research papers Structural study of a manganese(II) ‘picket-fence’ porphyrin complex ISSN 2053-2296
Qiang Yu,a,b Xiangjun Li,b Diansheng Liua and Jianfeng Lib* a
Research Institute of Applied Chemistry, Shanxi University, Taiyuan, Shanxi 030006, People’s Republic of China, and College of Materials Science and Opto-electronic Technology, University of Chinese Academy of Sciences, YianQi Lake, HuaiRou District, Beijing 101408, People’s Republic of China. *Correspondence e-mail: [email protected] b
Received 28 April 2015 Accepted 15 May 2015 Edited by A. L. Spek, Utrecht University, The Netherlands Keywords: picket-fence porphyrin; cryptand222; manganese(II); potassium; crystal structure; 24-atom mean plane; near-planar conformation. CCDC reference: 1401463 Supporting information: this article has supporting information at journals.iucr.org/c
‘Picket-fence’ porphyrin compounds are used in the investigation of interactions of hemes with dioxygen, carbon monoxide, nitric monoxide and imidazole ligands. (Cryptand-222)potassium chlorido[meso-tetra( , , , -o-pivalamidophenyl)porphyrinato]manganese tetrahydrofuran monosolvate (cryptand-222 is 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane), [K(C18H36N2O6)][Mn(C64H64N8O4)Cl]C4H8O or [K(222)][Mn(TpivPP)Cl]THF [systematic name for TpivPP: 5,10,15,20-tetrakis(2-tert-butanamidophenyl)porphyrin], is a fivecoordinate high-spin manganese(II) picket-fence porphyrin complex. It crystallizes with a potassium cation chelated inside a cryptand-222 molecule; the ˚ , respectively. average K—O and K—N distances are 2.83 (4) and 2.995 (13) A All four protecting tert-butyl pickets of the porphyrin are ordered. The porphyrin plane is nearly planar, as indicated by the atomic displacements and the dihedral angles between the mean planes of the pyrrole rings and the 24atom mean plane. The axial chloride ligand is located inside the molecular cavity on the hindered porphyrin side and the Mn—Cl bond is tilted slightly off the normal to the porphyrin plane by 3.68 (2) . The out-of-plane displacement of ˚, the metal centre relative to the 24-atom mean plane (24) is 0.7013 (4) A indicating a noticeable porphyrin core doming.
1. Introduction
# 2015 International Union of Crystallography
Acta Cryst. (2015). C71, 545–548
The picket-fence porphyrin model compound meso-tetra( , , , -o-pivalamidophenyl)porphyrin (denoted TpivPP) is a representative example used in the investigation of interactions of hemes with dioxygen, carbon monoxide, nitric monoxide and imidazole ligands. The first crystal structure of a picket-fence metalloporphyrin, namely [Fe(TpivPP)(1-MeIm)(O2)] (where 1-MeIm is 1-methylimidazole), was reported by Collman et al. (1975). Subsequently, many other iron and cobalt picket-fence porphyrin complexes were reported, e.g. four-coordinate [Co(TpivPP)] (Jene & Ibers, 2000), five-coordinate [K(222)][Fe(TpivPP)(OC6H5)] (Nasri et al., 1987), [Na(222)][Fe(TpivPP)(N3)] (Hachem et al., 2009), [Co(TpivPP)(2-MeHIm)] (2-MeHIm = 2-methylimidazole; Li et al., 2010), six-coordinate [Na(18C6)][Co(TpivPP)(SC6HF4)(O2)] (SC6HF4 = 2,3,5,6tetrafluorophenylthiolate and 18C6 = 18-crown-6; Doppelt et al., 1987), [Fe(TpivPP)(1-MeIm)2] (Li et al., 2008), [Co(TpivPP)(1-MeIm)(O2)] (Li et al., 2012) and [Fe(TpivPP)(1EtIm)(O2)] (1-EtIm = 1-ethylimidazole; Li et al., 2013). The geometric and electronic structures of three imidazole-ligated manganese(II) picket-fence porphyrin complexes have been reported recently, namely [Mn(TpivPP)(RIm)] (RIm = 1-MeIm, 1-EtIm and 2-MeHIm; Yu et al., 2015). We report here the structural properties of the five-coordinate picketfence porphyrin complex [K(222)][Mn(TpivPP)Cl]THF, (I). http://dx.doi.org/10.1107/S2053229615009304
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research papers 2. Experimental
Table 1
2.1. Synthesis and crystallization
Black block-shaped crystals were obtained from a frustrated attempt to obtain a manganese–peroxo porphyrin complex. [H2(TpivPP)], [MnIII(TpivPP)Cl] and [MnIII(TpivPP)]2O were prepared according to a local modification of a reported synthesis (Collman et al., 1975). [MnIII(TpivPP)]2O {10 mg, 9.33 10 3 mmol, with an [MnIII(TpivPP)Cl] impurity} was reduced in the presence of ethanethiol (1 ml). After a 48 h reaction time, the solution was evaporated to dryness under vacuum. The resulting purple solid was dried for an additional 30 min and then dissolved in tetrahydrofuran (THF, 2.5 ml). A twofold excess of kryptofix 222 and a fourfold excess potassium superoxide, KO2, were added to the solution. The mixture was stirred overnight and transferred to glass tubes which were layered with hexanes as nonsolvent. Crystals were collected after 30 d.
Experimental details. Crystal data Chemical formula Mr Crystal system, space group Temperature (K) ˚) a, b, c (A ( ) ˚ 3) V (A Z Radiation type (mm 1) Crystal size (mm) Data collection Diffractometer Absorption correction
[K(C18H36N2O6)][Mn(C64H64N8O4)Cl]C4H8O 1587.31 Monoclinic, P21/n 200 17.2598 (3), 21.2990 (3), 22.7585 (3) 96.378 (2) 8314.6 (2) 4 Mo K 0.31 0.20 0.20 0.10
Agilent Xcalibur (Eos, Gemini) diffractometer Multi-scan (CrysAlis PRO; Agilent, 2011) 0.984, 1.000 65981, 18558, 14238
Tmin, Tmax No. of measured, independent and observed [I > 2(I)] reflections Rint ˚ 1) (sin /)max (A
0.034 0.676
Refinement R[F 2 > 2(F 2)], wR(F 2), S No. of reflections No. of parameters No. of restraints H-atom treatment ˚ 3) max, min (e A
0.047, 0.113, 1.02 18558 992 5 H-atom parameters constrained 1.11, 0.97
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).
of weak distance restraints. No attempt was made to model the disorder.
3. Results and discussion
2.2. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were placed in ˚ and C—H = 0.95, calculated positions, with N—H = 0.88 A ˚ 0.98 or 0.99 A for aryl, methyl or methine H atoms, respectively, and refined using a riding model with fixed isotropic displacement parameters, i.e. Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) otherwise. The THF solvent molecule was found to be disordered and the C—C and C—O bond lengths appear unsatisfactory, even with the application
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[K(C18H36N2O6)][Mn(C64H64N8O4)Cl]C4H8O
In the title complex, [K(222)][Mn(TpivPP)Cl]THF, (I) (Fig. 1) (space group P21/n), the counter-ion to the negatively charged manganese(II) picket-fence porphyrinate is a potassium cation chelated inside a kryptofix 222 (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane, 222) molecule. The six O and two N atoms of kryptofix 222 bind to the potassium cation through electrostatic interactions. The average K—O ˚ , respecand K—N distances are 2.83 (4) and 2.995 (13) A tively. The axial chloride ligand of the anion is located inside the molecular cavity on the hindered porphyrin side. The Mn—Cl ˚ and is tilted slightly [by 3.68 (2) ] bond lengths is 2.3704 (6) A from the normal to the porphyrin plane (Fig. 2). The oxidation state of manganese can differ, but the observed Mn—Cl bond length in (I) is almost the same as that of [MnIII(TPP)Cl] [TPP ˚ ; Tulinsky & Chen, 1977]. is tetraphenylporphyrin; 2.363 (3) A The reason for the similar bond lengths with different oxidation states could be that for high-spin manganese(II), the occupied dx2–y2 orbital has little interaction with the axial ligand (VanAtta et al., 1987). All four protecting tert-butyl pickets are ordered, similar to the five-coordinate analogues Acta Cryst. (2015). C71, 545–548
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Figure 2 Diagram illustrating the off-axis tilt of the axial ligand, the near-planar conformation and the core dome of the [Mn(TpivPP)Cl] anion. The dashed line indicates the position of the normal to the porphyrin plane.
The porphyrin atoms of the [Mn(TpivPP)Cl] anion presents a near-planar conformation. The displacements of the porphyrin meso-C and -C atoms from the mean plane are ˚ (Fig. 3). The near-planar conformation can also be 0.11 A seen by noting the dihedral angles between the 24-atom mean plane and the pyrrole-ring mean planes. For the pyrrole rings containing atoms N1, N2 and N4, the dihedral angles are 1.39 (8), 4.29 (8) and 3.07 (8) , respectively. The N3-pyrrole ring has the largest dihedral angle [5.26 (8) ]. This is consistent with the slightly shorter Mn—N3 bond length [2.1452 (16) ˚ ]. FeIII is versus 2.1538 (16), 2.1529 (15) and 2.1550 (16) A II isoelectronic with Mn and a near-planar conformation was found in the molecular structure of [Fe(TpivPP)Cl] (Dhifet et al., 2011). The dihedral angles between the mean planes of the pendent benzene rings and the 24-atom mean plane in
Figure 1 Displacement ellipsoid plots (50% probability level) of the components of [K(222)][Mn(TpivPP)Cl]THF, (I), i.e. (a) the [Mn(TpivPP)Cl] anion, (b) the [K(222)]+ cation and (c) the THF solvent molecule, showing the atom-labelling scheme.
[Fe(TpivPP)Cl] (Dhifet et al., 2011) and [K(222)][Fe(TpivPP)Cl] (Schappacher et al., 1983). Additional quantitative information on the structure of (I) is given in Fig. 3, which displays the displacements of each ˚ ) from the 24-atom porphyrin core atom (in units of 0.01 A mean plane. The average Mn—Np (Np is a porphyrin N atom) ˚ . The out-of-plane displacement of bond length is 2.152 (4) A the metal centre relative to the 24-atom mean plane (24) is ˚ . As can be seen in Fig. 2, the porphyrin core 0.7013 (4) A presents an obvious doming. The overall structural features of [Mn(TpivPP)Cl] are those expected for a high-spin MnII species (Kirner et al., 1977). Acta Cryst. (2015). C71, 545–548
Figure 3 Formal diagram of the porphyrinate core of [Mn(TpivPP)Cl] . Averaged ˚ ) and angles (in ) values of the chemically unique bond distances (in A are shown. The numbers in parentheses are the s.u. values calculated assuming that the averaged values were all drawn from the same ˚ ) of the population. The perpendicular displacements (in units of 0.01 A porphyrin core atoms from the 24-atom mean plane are also displayed. In the diagram, positive values of the displacement are towards the hindered porphyrin side. Yu et al.
[K(C18H36N2O6)][Mn(C64H64N8O4)Cl]C4H8O
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research papers [K(222)][Mn(TpivPP)Cl] are more perpendicular than those in [K(222)][Mn(TPP)Cl] (VanAtta et al., 1987). For the benzene rings at atoms C301, C302, C303 and C304, the dihedral angles are 73.27 (5), 86.43 (5), 74.67 (4) and 78.09 (5) , respectively. However, in the structure of [K(222)][Mn(TPP)Cl], the corresponding angles are 67.15, 69.46, 89.04 and 55.99 . The reason for this could be the steric effect of the tert-butyl groups of the picket-fence porphyrin, which hinders the rotation of the benzene rings to which they are attached (Figs. 1 and 4).
Acknowledgements The authors thank the CAS Hundred Talent Program and the National Natural Science Foundation of China (grant no. 21371167, to JL).
References
Figure 4
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Collman, J. P., Gagne, R. R., Reed, C., Halbert, T. R., Lang, G. & Robinson, W. T. (1975). J. Am. Chem. Soc. 97, 1427–1439. Dhifet, M., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2011). Acta Cryst. E67, m460–m461. Doppelt, P., Fischer, J., Ricard, L. & Weiss, R. (1987). New J. Chem. 11, 357–364. Hachem, I., Belkhiria, M. S., Giorgi, M., Schulz, C. E. & Nasri, H. (2009). Polyhedron, 28, 954–958. Jene, P. G. & Ibers, J. A. (2000). Inorg. Chem. 39, 3823–3827. Kirner, J. F., Reed, C. A. & Scheidt, W. R. (1977). J. Am. Chem. Soc. 99, 2557–2563. Li, J., Nair, S. M., Noll, B. C., Schulz, C. E. & Scheidt, W. R. (2008). Inorg. Chem. 47, 3841–3850. Li, J., Noll, B. C., Oliver, A. G., Ferraudi, G., Lappin, A. G. & Scheidt, W. R. (2010). Inorg. Chem. 49, 2398–2406. Li, J., Noll, B. C., Oliver, A. G. & Scheidt, W. R. (2012). J. Am. Chem. Soc. 134, 10595–10606.
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View of the molecular packing of [K(222)][Mn(TpivPP)Cl]THF, (I), in the crystal. H atoms have been omitted for clarity.
Li, J., Noll, B. C., Oliver, A. G., Schulz, C. E. & Scheidt, W. R. (2013). J. Am. Chem. Soc. 135, 15627–15641. Nasri, H., Fischer, J., Weiss, R., Bill, E. & Trautwein, A. (1987). J. Am. Chem. Soc. 109, 2549–2550. Schappacher, M., Ricard, L., Weiss, R., Montiel-Montoya, R., Gonser, U., Bill, E. & Trautwein, A. (1983). Inorg. Chim. Acta, 78, L9–L12. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Tulinsky, A. & Chen, B. M. L. (1977). J. Am. Chem. Soc. 99, 3647– 3651. VanAtta, R. B., Strouse, C. E., Hanson, L. K. & Valentine, J. S. (1987). J. Am. Chem. Soc. 109, 1425–1434. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Yu, Q., Liu, Y. H., Liu, D. S. & Li, J. F. (2015). Dalton Trans. 44, 9382– 9390.
Acta Cryst. (2015). C71, 545–548
supporting information
supporting information Acta Cryst. (2015). C71, 545-548
[doi:10.1107/S2053229615009304]
Structural study of a manganese(II) `picket-fence′ porphyrin complex Qiang Yu, Xiangjun Li, Diansheng Liu and Jianfeng Li Computing details Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010). (4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)potassium chlorido[meso-5,10,15,20-tetrakis(2tert-butanamidophenyl)porphyrinato(2-)]manganese(II) tetrahydrofuran monosolvate Crystal data [K(C18H36N2O6)][MnCl(C64H64N8O4)]·C4H8O Mr = 1587.31 Monoclinic, P21/n a = 17.2598 (3) Å b = 21.2990 (3) Å c = 22.7585 (3) Å β = 96.378 (2)° V = 8314.6 (2) Å3 Z=4
F(000) = 3372 Dx = 1.268 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 17336 reflections θ = 3.0–28.7° µ = 0.31 mm−1 T = 200 K Block, black 0.20 × 0.20 × 0.10 mm
Data collection Agilent Xcalibur (Eos, Gemini) diffractometer Detector resolution: 16.2141 pixels mm-1 ω scans Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) Tmin = 0.984, Tmax = 1.000 65981 measured reflections
18558 independent reflections 14238 reflections with I > 2σ(I) Rint = 0.034 θmax = 28.7°, θmin = 3.0° h = −23→19 k = −28→27 l = −28→29
Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.047 wR(F2) = 0.113 S = 1.02 18558 reflections 992 parameters 5 restraints
Acta Cryst. (2015). C71, 545-548
Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0411P)2 + 8.2684P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.003 Δρmax = 1.11 e Å−3 Δρmin = −0.97 e Å−3
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supporting information Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Cl1 K1 Mn1 C101 C102 C103 C104 C105 C106 C107 C108 C201 H20A C202 H20B C203 H20C C204 H20D C205 H20E C206 H20F C207 H20G C208 H20H C301 C302 C303 C304 N1 N2 N3 N4
x
y
z
Uiso*/Ueq
0.97749 (3) 1.24267 (3) 1.03128 (2) 0.97515 (11) 0.89637 (11) 0.90017 (11) 0.98416 (11) 1.11881 (11) 1.19913 (11) 1.19430 (11) 1.10914 (12) 0.90592 (12) 0.8963 0.85766 (12) 0.8075 0.86796 (12) 0.8198 0.91904 (12) 0.9134 1.19125 (12) 1.2020 1.24077 (12) 1.2929 1.23004 (12) 1.2807 1.17776 (12) 1.1848 1.04113 (12) 0.86537 (11) 1.05262 (11) 1.23065 (11) 0.96709 (9) 0.97041 (9) 1.12525 (9) 1.12068 (9)
0.96273 (3) 0.83486 (2) 0.93078 (2) 0.79137 (9) 0.85782 (9) 0.97245 (9) 1.04917 (9) 1.05626 (9) 0.98915 (9) 0.87459 (9) 0.79850 (9) 0.75679 (9) 0.7135 0.79761 (9) 0.7885 1.02762 (9) 1.0301 1.07491 (9) 1.1171 1.08912 (9) 1.1317 1.04800 (9) 1.0561 0.81770 (9) 0.8139 0.77105 (9) 0.7282 0.76548 (9) 0.91263 (9) 1.08175 (8) 0.93356 (9) 0.85288 (7) 0.98696 (7) 0.99570 (7) 0.86154 (7)
0.82146 (2) 0.54958 (2) 0.73482 (2) 0.71035 (8) 0.66039 (8) 0.63512 (8) 0.65560 (8) 0.70925 (8) 0.75751 (8) 0.78299 (8) 0.76439 (8) 0.68826 (9) 0.6943 0.65756 (9) 0.6377 0.60465 (9) 0.5802 0.61741 (8) 0.6039 0.72555 (8) 0.7170 0.75514 (9) 0.7713 0.80801 (9) 0.8287 0.79640 (9) 0.8072 0.74344 (8) 0.63264 (8) 0.67595 (8) 0.78361 (8) 0.69335 (7) 0.66582 (7) 0.72941 (7) 0.75741 (7)
0.02712 (12) 0.02032 (10) 0.01402 (7) 0.0165 (4) 0.0167 (4) 0.0150 (4) 0.0147 (4) 0.0151 (4) 0.0157 (4) 0.0169 (4) 0.0169 (4) 0.0215 (4) 0.026* 0.0213 (4) 0.026* 0.0188 (4) 0.023* 0.0181 (4) 0.022* 0.0179 (4) 0.021* 0.0185 (4) 0.022* 0.0205 (4) 0.025* 0.0207 (4) 0.025* 0.0165 (4) 0.0155 (4) 0.0146 (4) 0.0162 (4) 0.0155 (3) 0.0143 (3) 0.0146 (3) 0.0163 (3)
Acta Cryst. (2015). C71, 545-548
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supporting information C1 C2 H2A C3 H3A C4 H4A C5 H5A C6 C7 C8 C9 H9A H9B H9C C10 H10A H10B H10C C11 H11A H11B H11C C12 C13 H13A C14 H14A C15 H15A C16 H16A C17 C18 C19 C20 H20I H20J H20K C21 H21A H21B H21C C22 H22A H22B H22C
1.03725 (11) 1.04129 (12) 1.0494 1.03375 (14) 1.0371 1.02134 (14) 1.0156 1.01716 (14) 1.0090 1.02489 (13) 1.01490 (12) 1.01983 (14) 0.98399 (16) 0.9300 1.0142 0.9848 1.10654 (15) 1.1330 1.1122 1.1299 0.97894 (18) 1.0024 0.9846 0.9235 0.78675 (12) 0.77998 (13) 0.8255 0.70741 (14) 0.7032 0.64133 (13) 0.5916 0.64638 (13) 0.6004 0.71942 (12) 0.67842 (12) 0.71798 (12) 0.65501 (14) 0.6197 0.6254 0.6794 0.76366 (14) 0.8040 0.7280 0.7882 0.77277 (14) 0.8133 0.7971 0.7430
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0.69649 (9) 0.65275 (9) 0.6669 0.58907 (10) 0.5599 0.56839 (10) 0.5248 0.61058 (10) 0.5959 0.67494 (9) 0.71404 (10) 0.77528 (10) 0.83125 (11) 0.8214 0.8402 0.8681 0.78806 (12) 0.7948 0.8256 0.7520 0.76489 (13) 0.7289 0.8025 0.7566 0.90490 (9) 0.88326 (10) 0.8773 0.87030 (10) 0.8544 0.88063 (10) 0.8726 0.90258 (10) 0.9102 0.91347 (10) 0.92934 (10) 0.93555 (10) 0.93514 (13) 0.9708 0.8959 0.9385 0.99744 (11) 0.9974 1.0327 1.0018 0.87984 (11) 0.8799 0.8833 0.8406
0.75621 (9) 0.71149 (9) 0.6731 0.72143 (10) 0.6903 0.77712 (10) 0.7841 0.82283 (10) 0.8611 0.81275 (9) 0.91515 (9) 0.95107 (9) 0.91606 (11) 0.9008 0.8830 0.9420 0.96934 (12) 0.9339 0.9943 0.9914 1.00635 (11) 1.0284 1.0313 0.9948 0.59845 (9) 0.54047 (9) 0.5212 0.51064 (10) 0.4714 0.53809 (10) 0.5172 0.59557 (10) 0.6139 0.62637 (9) 0.72783 (10) 0.79131 (10) 0.83337 (11) 0.8244 0.8285 0.8742 0.79764 (11) 0.7705 0.7881 0.8384 0.80564 (11) 0.7787 0.8465 0.8008
0.0180 (4) 0.0213 (4) 0.026* 0.0268 (5) 0.032* 0.0296 (5) 0.036* 0.0292 (5) 0.035* 0.0224 (4) 0.0219 (4) 0.0258 (5) 0.0362 (6) 0.054* 0.054* 0.054* 0.0392 (6) 0.059* 0.059* 0.059* 0.0427 (7) 0.064* 0.064* 0.064* 0.0184 (4) 0.0231 (4) 0.028* 0.0278 (5) 0.033* 0.0288 (5) 0.035* 0.0274 (5) 0.033* 0.0215 (4) 0.0235 (4) 0.0246 (5) 0.0349 (6) 0.052* 0.052* 0.052* 0.0327 (5) 0.049* 0.049* 0.049* 0.0311 (5) 0.047* 0.047* 0.047*
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supporting information C23 C24 H24A C25 H25A C26 H26A C27 H27A C28 C29 C30 C31 H31A H31B H31C C32 H32A H32B H32C C33 H33A H33B H33C C34 C35 H35A C36 H36A C37 H37A C38 H38A C39 C40 C41 C42 H42A H42B H42C C43 H43A H43B H43C C44 H44A H44B H44C
1.05898 (11) 1.10624 (12) 1.1332 1.11491 (12) 1.1470 1.07609 (12) 1.0819 1.02905 (12) 1.0030 1.01956 (11) 0.91079 (12) 0.87020 (13) 0.86661 (15) 0.8408 0.8371 0.9196 0.91032 (15) 0.9635 0.8810 0.9123 0.78705 (14) 0.7617 0.7888 0.7575 1.31150 (11) 1.37498 (12) 1.3667 1.45029 (12) 1.4934 1.46185 (12) 1.5133 1.39985 (12) 1.4088 1.32409 (12) 1.25169 (13) 1.16770 (13) 1.12256 (15) 1.1206 1.1487 1.0694 1.12716 (16) 1.1259 1.0738 1.1559 1.17019 (17) 1.1990 1.1169 1.1962
Acta Cryst. (2015). C71, 545-548
1.14865 (9) 1.16328 (9) 1.1305 1.22454 (10) 1.2336 1.27234 (9) 1.3145 1.25913 (9) 1.2923 1.19760 (9) 1.21558 (10) 1.18985 (10) 1.24381 (11) 1.2801 1.2304 1.2555 1.13319 (12) 1.1447 1.1198 1.0987 1.17247 (12) 1.2091 1.1381 1.1591 0.93851 (9) 0.91747 (9) 0.8988 0.92319 (9) 0.9095 0.94905 (10) 0.9522 0.97045 (10) 0.9883 0.96565 (9) 1.01610 (10) 1.02912 (11) 0.96738 (12) 0.9471 0.9396 0.9759 1.07239 (13) 1.0520 1.0808 1.1120 1.06009 (15) 1.0997 1.0684 1.0321
0.65651 (8) 0.61260 (9) 0.5952 0.59375 (9) 0.5635 0.61968 (9) 0.6073 0.66328 (9) 0.6809 0.68158 (8) 0.74252 (9) 0.79408 (9) 0.83828 (10) 0.8181 0.8704 0.8545 0.82526 (11) 0.8413 0.8575 0.7969 0.76875 (11) 0.7488 0.7403 0.8009 0.81507 (8) 0.78820 (9) 0.7501 0.81594 (9) 0.7967 0.87173 (10) 0.8912 0.89987 (9) 0.9383 0.87165 (9) 0.94914 (9) 0.96172 (10) 0.96264 (12) 0.9239 0.9929 0.9717 0.91395 (13) 0.8753 0.9226 0.9135 1.02221 (13) 1.0221 1.0312 1.0523
0.0150 (4) 0.0200 (4) 0.024* 0.0224 (4) 0.027* 0.0213 (4) 0.026* 0.0200 (4) 0.024* 0.0161 (4) 0.0214 (4) 0.0230 (4) 0.0334 (5) 0.050* 0.050* 0.050* 0.0358 (6) 0.054* 0.054* 0.054* 0.0353 (6) 0.053* 0.053* 0.053* 0.0167 (4) 0.0194 (4) 0.023* 0.0213 (4) 0.026* 0.0229 (4) 0.027* 0.0229 (4) 0.028* 0.0204 (4) 0.0235 (4) 0.0288 (5) 0.0410 (6) 0.062* 0.062* 0.062* 0.0455 (7) 0.068* 0.068* 0.068* 0.0512 (8) 0.077* 0.077* 0.077*
sup-4
supporting information N5 H5 N6 H6A N7 H7A N8 H8A O1 O2 O3 O4 C45 H45A H45B C46 H46A H46B C47 H47A H47B C48 H48A H48B C49 H49A H49B C50 H50A H50B C51 H51A H51B C52 H52A H52B C53 H53A H53B C54 H54A H54B C55 H55A H55B C56 H56A H56B
1.01866 (12) 1.0169 0.72999 (10) 0.7770 0.97367 (10) 0.9870 1.25761 (10) 1.2128 1.01091 (11) 0.60861 (9) 0.88698 (10) 1.30841 (10) 1.10066 (15) 1.0632 1.0736 1.16806 (16) 1.2073 1.1499 1.26249 (14) 1.2418 1.3048 1.29397 (14) 1.3343 1.2516 1.36470 (14) 1.3255 1.3994 1.41170 (13) 1.4486 1.4429 1.15582 (15) 1.1901 1.1127 1.20183 (15) 1.1700 1.2157 1.31928 (14) 1.3333 1.2910 1.39149 (13) 1.4284 1.4172 1.43878 (13) 1.4662 1.4749 1.41402 (13) 1.3855 1.4612
Acta Cryst. (2015). C71, 545-548
0.72094 (8) 0.7600 0.93052 (9) 0.9440 1.18289 (8) 1.1491 0.98548 (9) 0.9767 0.66306 (7) 0.92353 (8) 1.26286 (8) 1.03157 (8) 0.71835 (12) 0.7505 0.6773 0.71585 (11) 0.6853 0.7020 0.77805 (12) 0.7640 0.7490 0.84330 (12) 0.8448 0.8726 0.92053 (11) 0.9543 0.9214 0.93084 (11) 0.8954 0.9697 0.67707 (11) 0.6554 0.6480 0.69025 (12) 0.7154 0.6503 0.73152 (12) 0.6900 0.7554 0.76615 (11) 0.7675 0.7443 0.86426 (10) 0.8460 0.8640 0.93042 (10) 0.9474 0.9565
0.85641 (8) 0.8436 0.68634 (8) 0.6992 0.72734 (7) 0.7483 0.89729 (8) 0.8765 0.93834 (7) 0.71525 (7) 0.71641 (8) 0.98270 (7) 0.47510 (11) 0.4581 0.4723 0.43892 (11) 0.4564 0.3982 0.40014 (10) 0.3600 0.4155 0.39747 (9) 0.3698 0.3830 0.45440 (10) 0.4467 0.4226 0.51358 (10) 0.5214 0.5116 0.56856 (11) 0.5429 0.5748 0.62732 (11) 0.6522 0.6480 0.67259 (10) 0.6901 0.7008 0.66123 (10) 0.6978 0.6303 0.63496 (10) 0.6030 0.6719 0.61939 (10) 0.6513 0.6176
0.0294 (4) 0.035* 0.0280 (4) 0.034* 0.0185 (3) 0.022* 0.0259 (4) 0.031* 0.0340 (4) 0.0342 (4) 0.0380 (4) 0.0359 (4) 0.0342 (6) 0.041* 0.041* 0.0345 (6) 0.041* 0.041* 0.0321 (5) 0.038* 0.038* 0.0307 (5) 0.037* 0.037* 0.0290 (5) 0.035* 0.035* 0.0270 (5) 0.032* 0.032* 0.0347 (6) 0.042* 0.042* 0.0346 (6) 0.042* 0.042* 0.0317 (5) 0.038* 0.038* 0.0285 (5) 0.034* 0.034* 0.0260 (5) 0.031* 0.031* 0.0272 (5) 0.033* 0.033*
sup-5
supporting information C57 H57A H57B C58 H58A H58B C59 H59A H59B C60 H60A H60B C61 H61A H61B C62 H62A H62B N9 N10 O5 O6 O7 O8 O9 O10 C1S H1SA H1SB C2S H2SA H2SB C3S H3SA H3SB C4S H4SA H4SB O1S
1.05497 (14) 1.0684 1.0119 1.02657 (14) 1.0129 0.9794 1.06258 (13) 1.0100 1.0603 1.11973 (14) 1.1022 1.1232 1.25191 (14) 1.2627 1.2330 1.32497 (14) 1.3116 1.3614 1.12303 (11) 1.36440 (10) 1.20222 (9) 1.32680 (9) 1.27090 (9) 1.37130 (8) 1.08639 (9) 1.19450 (9) 0.8305 (3) 0.7983 0.8485 0.7867 (2) 0.7939 0.7306 0.8140 (3) 0.7700 0.8330 0.8726 (3) 0.9156 0.8530 0.9006 (3)
0.75530 (12) 0.7560 0.7249 0.81928 (12) 0.8196 0.8303 0.92577 (11) 0.9337 0.9317 0.97002 (11) 1.0137 0.9628 0.99785 (11) 0.9801 1.0414 0.99754 (10) 1.0097 1.0294 0.73303 (9) 0.93620 (8) 0.77693 (7) 0.86139 (7) 0.72376 (7) 0.82805 (7) 0.86347 (7) 0.96118 (7) 0.6000 (2) 0.5620 0.6002 0.6539 (2) 0.6852 0.6433 0.6784 (3) 0.6801 0.7218 0.64305 (16) 0.6704 0.6184 0.59968 (19)
0.56505 (12) 0.6085 0.5561 0.54515 (11) 0.5017 0.5640 0.54597 (10) 0.5579 0.5027 0.57695 (11) 0.5690 0.6201 0.59118 (11) 0.6314 0.5946 0.56081 (11) 0.5189 0.5796 0.53768 (8) 0.56310 (8) 0.43767 (7) 0.45499 (6) 0.61824 (6) 0.64252 (6) 0.56131 (7) 0.55722 (7) 0.59808 (19) 0.5890 0.6409 0.58276 (17) 0.6151 0.5754 0.5303 (3) 0.4985 0.5379 0.51159 (13) 0.5016 0.4761 0.56226 (17)
0.0355 (6) 0.043* 0.043* 0.0344 (6) 0.041* 0.041* 0.0292 (5) 0.035* 0.035* 0.0322 (5) 0.039* 0.039* 0.0308 (5) 0.037* 0.037* 0.0296 (5) 0.035* 0.035* 0.0279 (4) 0.0222 (4) 0.0281 (3) 0.0275 (3) 0.0270 (3) 0.0246 (3) 0.0286 (3) 0.0266 (3) 0.107 (2) 0.129* 0.129* 0.0717 (11) 0.086* 0.086* 0.148 (3) 0.178* 0.178* 0.0720 (12) 0.086* 0.086* 0.1484 (17)
Atomic displacement parameters (Å2)
Cl1 K1 Mn1 C101 C102
U11
U22
U33
U12
U13
U23
0.0302 (3) 0.0197 (2) 0.01294 (14) 0.0174 (10) 0.0145 (9)
0.0293 (3) 0.0203 (2) 0.01214 (14) 0.0139 (9) 0.0157 (9)
0.0231 (2) 0.0209 (2) 0.01662 (14) 0.0185 (9) 0.0201 (9)
0.0045 (2) 0.00031 (17) 0.00003 (11) −0.0004 (8) −0.0019 (8)
0.0085 (2) 0.00216 (17) 0.00004 (11) 0.0036 (8) 0.0034 (8)
−0.0006 (2) −0.00032 (17) 0.00194 (11) 0.0005 (7) −0.0016 (8)
Acta Cryst. (2015). C71, 545-548
sup-6
supporting information C103 C104 C105 C106 C107 C108 C201 C202 C203 C204 C205 C206 C207 C208 C301 C302 C303 C304 N1 N2 N3 N4 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26
0.0130 (9) 0.0156 (9) 0.0163 (9) 0.0144 (9) 0.0160 (10) 0.0183 (10) 0.0196 (10) 0.0187 (10) 0.0156 (10) 0.0182 (10) 0.0204 (10) 0.0157 (10) 0.0179 (10) 0.0219 (11) 0.0197 (10) 0.0132 (9) 0.0166 (10) 0.0128 (9) 0.0152 (8) 0.0131 (8) 0.0141 (8) 0.0153 (8) 0.0165 (10) 0.0229 (11) 0.0329 (13) 0.0394 (14) 0.0418 (14) 0.0269 (11) 0.0205 (11) 0.0321 (12) 0.0515 (16) 0.0385 (15) 0.0625 (19) 0.0163 (10) 0.0230 (11) 0.0322 (13) 0.0219 (11) 0.0175 (11) 0.0175 (10) 0.0157 (10) 0.0156 (10) 0.0212 (12) 0.0293 (13) 0.0251 (12) 0.0140 (9) 0.0194 (10) 0.0200 (11) 0.0194 (10)
Acta Cryst. (2015). C71, 545-548
0.0161 (9) 0.0138 (9) 0.0138 (9) 0.0158 (9) 0.0168 (9) 0.0142 (9) 0.0164 (10) 0.0170 (10) 0.0187 (10) 0.0150 (9) 0.0128 (9) 0.0189 (10) 0.0188 (10) 0.0149 (9) 0.0134 (9) 0.0163 (9) 0.0129 (9) 0.0191 (10) 0.0133 (8) 0.0131 (8) 0.0133 (8) 0.0146 (8) 0.0133 (9) 0.0186 (10) 0.0163 (10) 0.0137 (10) 0.0178 (10) 0.0159 (10) 0.0229 (11) 0.0227 (11) 0.0245 (12) 0.0274 (12) 0.0408 (15) 0.0130 (9) 0.0205 (10) 0.0243 (11) 0.0281 (12) 0.0278 (12) 0.0190 (10) 0.0202 (10) 0.0267 (11) 0.0489 (15) 0.0304 (12) 0.0334 (13) 0.0133 (9) 0.0170 (10) 0.0212 (10) 0.0140 (9)
0.0161 (9) 0.0153 (9) 0.0154 (9) 0.0167 (9) 0.0178 (9) 0.0182 (9) 0.0282 (11) 0.0275 (11) 0.0215 (10) 0.0207 (9) 0.0203 (9) 0.0204 (9) 0.0240 (10) 0.0250 (10) 0.0168 (9) 0.0172 (9) 0.0149 (8) 0.0164 (9) 0.0179 (8) 0.0167 (8) 0.0159 (7) 0.0186 (8) 0.0240 (10) 0.0230 (10) 0.0313 (11) 0.0356 (12) 0.0291 (11) 0.0248 (10) 0.0214 (10) 0.0226 (10) 0.0325 (12) 0.0494 (15) 0.0265 (12) 0.0249 (10) 0.0249 (10) 0.0242 (11) 0.0330 (12) 0.0358 (12) 0.0272 (10) 0.0347 (12) 0.0321 (11) 0.0358 (13) 0.0390 (13) 0.0345 (12) 0.0168 (9) 0.0239 (10) 0.0262 (11) 0.0293 (11)
0.0007 (7) 0.0011 (7) 0.0007 (7) −0.0001 (7) 0.0028 (8) 0.0018 (8) −0.0033 (8) −0.0041 (8) 0.0011 (8) 0.0019 (8) −0.0008 (8) −0.0026 (8) 0.0033 (8) 0.0044 (8) 0.0008 (8) −0.0015 (7) 0.0000 (7) 0.0010 (8) −0.0006 (6) −0.0003 (6) 0.0005 (6) 0.0004 (6) 0.0012 (8) −0.0005 (8) 0.0007 (9) 0.0018 (9) 0.0010 (10) 0.0019 (8) −0.0008 (8) 0.0007 (9) 0.0100 (11) −0.0037 (11) −0.0072 (13) −0.0018 (8) −0.0009 (9) −0.0062 (9) −0.0073 (9) −0.0038 (9) −0.0020 (8) −0.0019 (8) −0.0018 (9) −0.0017 (11) −0.0079 (10) 0.0027 (10) −0.0013 (7) 0.0003 (8) −0.0030 (8) −0.0030 (8)
0.0020 (7) 0.0043 (7) 0.0022 (7) 0.0016 (7) 0.0018 (8) 0.0023 (8) 0.0013 (8) −0.0011 (8) −0.0014 (8) 0.0005 (8) 0.0014 (8) −0.0002 (8) −0.0011 (8) 0.0004 (8) 0.0038 (8) 0.0018 (7) 0.0038 (7) 0.0003 (7) 0.0009 (6) 0.0018 (6) −0.0003 (6) 0.0007 (6) 0.0013 (8) 0.0046 (8) 0.0043 (10) 0.0041 (10) 0.0091 (10) 0.0043 (9) −0.0010 (8) 0.0023 (9) 0.0042 (11) −0.0052 (12) 0.0131 (12) −0.0027 (8) −0.0007 (9) −0.0084 (9) −0.0113 (9) −0.0019 (9) −0.0012 (8) 0.0035 (9) 0.0049 (9) 0.0084 (10) 0.0058 (10) 0.0019 (10) −0.0025 (7) 0.0035 (8) 0.0034 (8) −0.0034 (8)
0.0000 (7) 0.0001 (7) −0.0009 (7) −0.0006 (7) 0.0012 (8) 0.0024 (8) 0.0014 (8) 0.0011 (8) 0.0028 (8) 0.0032 (8) −0.0012 (8) −0.0013 (8) 0.0043 (8) 0.0054 (8) 0.0021 (7) 0.0004 (7) −0.0012 (7) −0.0007 (8) 0.0017 (6) 0.0012 (6) 0.0011 (6) 0.0020 (6) 0.0028 (8) 0.0021 (8) −0.0003 (9) 0.0044 (9) 0.0078 (9) 0.0023 (8) 0.0051 (8) 0.0020 (9) −0.0010 (10) −0.0052 (11) −0.0025 (11) 0.0050 (8) 0.0028 (9) 0.0022 (9) 0.0087 (10) 0.0078 (10) 0.0028 (8) −0.0012 (9) −0.0051 (9) −0.0040 (11) −0.0090 (11) 0.0002 (10) 0.0005 (7) −0.0002 (8) 0.0057 (9) 0.0058 (8)
sup-7
supporting information C27 C28 C29 C30 C31 C32 C33 C34 C35 C36 C37 C38 C39 C40 C41 C42 C43 C44 N5 N6 N7 N8 O1 O2 O3 O4 C45 C46 C47 C48 C49 C50 C51 C52 C53 C54 C55 C56 C57 C58 C59 C60 C61 C62 N9 N10 O5 O6
0.0204 (10) 0.0150 (9) 0.0204 (11) 0.0246 (11) 0.0375 (14) 0.0410 (15) 0.0312 (13) 0.0149 (10) 0.0193 (10) 0.0155 (10) 0.0141 (10) 0.0186 (10) 0.0173 (10) 0.0252 (11) 0.0236 (12) 0.0344 (14) 0.0304 (14) 0.0366 (16) 0.0519 (13) 0.0138 (9) 0.0206 (9) 0.0140 (9) 0.0537 (11) 0.0137 (8) 0.0376 (10) 0.0265 (9) 0.0334 (13) 0.0454 (15) 0.0329 (13) 0.0297 (13) 0.0262 (12) 0.0203 (11) 0.0360 (14) 0.0338 (14) 0.0334 (13) 0.0276 (12) 0.0196 (11) 0.0237 (11) 0.0240 (12) 0.0200 (12) 0.0225 (11) 0.0284 (12) 0.0306 (13) 0.0277 (12) 0.0274 (10) 0.0193 (9) 0.0302 (9) 0.0274 (8)
Acta Cryst. (2015). C71, 545-548
0.0131 (9) 0.0147 (9) 0.0203 (10) 0.0224 (10) 0.0326 (13) 0.0343 (13) 0.0435 (15) 0.0148 (9) 0.0153 (9) 0.0161 (10) 0.0227 (10) 0.0290 (11) 0.0204 (10) 0.0203 (10) 0.0305 (12) 0.0402 (15) 0.0450 (16) 0.068 (2) 0.0139 (8) 0.0405 (11) 0.0136 (8) 0.0406 (11) 0.0240 (8) 0.0492 (11) 0.0329 (9) 0.0440 (10) 0.0322 (13) 0.0264 (12) 0.0400 (14) 0.0440 (14) 0.0328 (12) 0.0277 (11) 0.0262 (12) 0.0335 (13) 0.0353 (13) 0.0290 (12) 0.0312 (12) 0.0267 (11) 0.0399 (14) 0.0457 (15) 0.0366 (13) 0.0338 (13) 0.0222 (11) 0.0177 (10) 0.0271 (10) 0.0192 (9) 0.0285 (8) 0.0342 (9)
0.0258 (10) 0.0177 (9) 0.0236 (10) 0.0227 (10) 0.0315 (12) 0.0342 (13) 0.0317 (12) 0.0195 (9) 0.0236 (10) 0.0325 (11) 0.0306 (11) 0.0198 (10) 0.0233 (10) 0.0249 (10) 0.0326 (12) 0.0516 (16) 0.0607 (18) 0.0502 (17) 0.0240 (9) 0.0294 (10) 0.0216 (8) 0.0224 (9) 0.0226 (8) 0.0396 (9) 0.0466 (10) 0.0355 (9) 0.0352 (13) 0.0301 (12) 0.0233 (11) 0.0186 (10) 0.0294 (11) 0.0341 (12) 0.0415 (14) 0.0360 (13) 0.0256 (11) 0.0273 (11) 0.0265 (11) 0.0308 (11) 0.0436 (14) 0.0378 (13) 0.0294 (11) 0.0362 (12) 0.0395 (13) 0.0438 (13) 0.0285 (10) 0.0282 (9) 0.0256 (8) 0.0211 (7)
0.0004 (8) −0.0012 (7) 0.0022 (8) 0.0022 (9) 0.0003 (11) 0.0090 (11) −0.0092 (11) −0.0001 (7) 0.0011 (8) 0.0024 (8) −0.0015 (8) −0.0041 (9) 0.0003 (8) 0.0003 (9) −0.0012 (9) −0.0091 (12) 0.0114 (12) −0.0015 (14) 0.0028 (8) −0.0066 (8) 0.0028 (7) 0.0002 (8) −0.0088 (8) −0.0033 (7) 0.0188 (8) −0.0007 (8) −0.0088 (11) −0.0012 (11) 0.0089 (11) 0.0058 (11) 0.0009 (10) −0.0021 (9) −0.0094 (10) −0.0086 (11) 0.0005 (11) 0.0028 (10) −0.0022 (9) −0.0031 (9) −0.0104 (10) −0.0047 (10) 0.0094 (10) 0.0083 (10) 0.0051 (10) −0.0020 (9) −0.0046 (8) 0.0012 (7) 0.0019 (7) −0.0034 (7)
−0.0010 (8) −0.0019 (7) 0.0027 (8) 0.0060 (9) 0.0093 (10) 0.0140 (11) 0.0059 (10) −0.0015 (8) 0.0025 (8) 0.0036 (8) −0.0030 (8) −0.0034 (8) 0.0010 (8) 0.0019 (9) 0.0041 (9) 0.0184 (12) 0.0040 (13) 0.0110 (13) 0.0109 (9) 0.0017 (7) 0.0039 (7) −0.0019 (7) −0.0039 (7) 0.0029 (7) 0.0192 (8) −0.0035 (7) −0.0045 (11) −0.0022 (11) 0.0032 (10) 0.0042 (9) 0.0094 (9) 0.0081 (9) 0.0025 (11) 0.0021 (11) −0.0002 (10) −0.0047 (9) −0.0010 (9) 0.0018 (9) 0.0083 (11) 0.0039 (10) 0.0076 (9) 0.0114 (10) 0.0041 (10) 0.0062 (10) 0.0002 (8) 0.0040 (7) 0.0031 (7) 0.0027 (6)
−0.0010 (8) 0.0002 (8) −0.0010 (8) −0.0008 (9) −0.0072 (10) 0.0123 (11) 0.0004 (11) 0.0044 (8) 0.0025 (8) 0.0048 (9) 0.0074 (9) 0.0021 (9) 0.0036 (8) −0.0004 (9) −0.0103 (10) −0.0085 (13) 0.0009 (14) −0.0302 (15) 0.0049 (7) −0.0059 (9) 0.0029 (7) −0.0065 (8) 0.0081 (7) −0.0027 (8) 0.0166 (8) −0.0168 (8) −0.0056 (10) −0.0085 (10) −0.0082 (10) −0.0006 (10) 0.0065 (10) 0.0013 (10) 0.0032 (11) 0.0131 (11) 0.0110 (10) 0.0069 (9) −0.0021 (9) −0.0070 (10) 0.0009 (11) −0.0047 (11) −0.0032 (10) −0.0094 (10) −0.0103 (10) −0.0023 (10) −0.0004 (8) −0.0017 (7) −0.0063 (7) 0.0021 (6)
sup-8
supporting information O7 O8 O9 O10 C1S C2S C3S C4S O1S
0.0259 (8) 0.0184 (7) 0.0197 (8) 0.0245 (8) 0.173 (5) 0.047 (2) 0.069 (3) 0.132 (4) 0.208 (5)
0.0293 (8) 0.0260 (8) 0.0333 (9) 0.0254 (8) 0.094 (3) 0.095 (3) 0.221 (7) 0.056 (2) 0.121 (3)
0.0251 (8) 0.0286 (8) 0.0325 (8) 0.0308 (8) 0.060 (2) 0.078 (2) 0.162 (5) 0.0294 (15) 0.104 (3)
−0.0033 (7) 0.0004 (6) 0.0009 (7) 0.0036 (6) −0.073 (4) 0.0011 (19) 0.038 (4) 0.028 (2) 0.046 (3)
0.0006 (6) 0.0000 (6) 0.0018 (6) 0.0078 (6) 0.040 (3) 0.0303 (18) 0.043 (3) 0.0154 (18) −0.036 (3)
0.0078 (6) 0.0032 (6) −0.0007 (7) −0.0080 (7) 0.004 (2) 0.044 (2) 0.146 (5) 0.0140 (14) 0.006 (2)
Geometric parameters (Å, º) Cl1—Mn1 K1—O6 K1—O9 K1—O10 K1—O5 K1—O7 K1—O8 K1—N9 K1—N10 Mn1—N3 Mn1—N2 Mn1—N1 Mn1—N4 C101—N1 C101—C301 C101—C201 C102—N1 C102—C302 C102—C202 C103—N2 C103—C302 C103—C203 C104—N2 C104—C303 C104—C204 C105—N3 C105—C303 C105—C205 C106—N3 C106—C304 C106—C206 C107—N4 C107—C304 C107—C207 C108—N4 C108—C301
Acta Cryst. (2015). C71, 545-548
2.3704 (6) 2.7851 (15) 2.8068 (16) 2.8271 (15) 2.8463 (15) 2.8478 (15) 2.8950 (15) 2.9862 (19) 3.0039 (18) 2.1452 (16) 2.1529 (15) 2.1538 (16) 2.1550 (16) 1.369 (2) 1.406 (3) 1.445 (3) 1.364 (2) 1.405 (3) 1.444 (3) 1.366 (2) 1.407 (3) 1.444 (3) 1.370 (2) 1.404 (3) 1.450 (3) 1.369 (2) 1.408 (3) 1.445 (3) 1.369 (2) 1.407 (3) 1.449 (3) 1.366 (2) 1.403 (3) 1.448 (3) 1.369 (2) 1.406 (3)
C30—C32 C30—C33 C30—C31 C31—H31A C31—H31B C31—H31C C32—H32A C32—H32B C32—H32C C33—H33A C33—H33B C33—H33C C34—C35 C34—C39 C35—C36 C35—H35A C36—C37 C36—H36A C37—C38 C37—H37A C38—C39 C38—H38A C39—N8 C40—O4 C40—N8 C40—C41 C41—C44 C41—C42 C41—C43 C42—H42A C42—H42B C42—H42C C43—H43A C43—H43B C43—H43C C44—H44A
1.527 (3) 1.531 (3) 1.533 (3) 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 1.387 (3) 1.406 (3) 1.386 (3) 0.9500 1.378 (3) 0.9500 1.384 (3) 0.9500 1.395 (3) 0.9500 1.409 (3) 1.218 (3) 1.362 (3) 1.534 (3) 1.523 (3) 1.530 (3) 1.534 (4) 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800
sup-9
supporting information C108—C208 C201—C202 C201—H20A C202—H20B C203—C204 C203—H20C C204—H20D C205—C206 C205—H20E C206—H20F C207—C208 C207—H20G C208—H20H C301—C1 C302—C12 C303—C23 C304—C34 C1—C2 C1—C6 C2—C3 C2—H2A C3—C4 C3—H3A C4—C5 C4—H4A C5—C6 C5—H5A C6—N5 C7—O1 C7—N5 C7—C8 C8—C11 C8—C9 C8—C10 C9—H9A C9—H9B C9—H9C C10—H10A C10—H10B C10—H10C C11—H11A C11—H11B C11—H11C C12—C13 C12—C17 C13—C14 C13—H13A C14—C15
Acta Cryst. (2015). C71, 545-548
1.443 (3) 1.345 (3) 0.9500 0.9500 1.349 (3) 0.9500 0.9500 1.350 (3) 0.9500 0.9500 1.348 (3) 0.9500 0.9500 1.501 (3) 1.496 (3) 1.500 (3) 1.500 (3) 1.387 (3) 1.405 (3) 1.384 (3) 0.9500 1.381 (3) 0.9500 1.383 (3) 0.9500 1.399 (3) 0.9500 1.408 (3) 1.213 (2) 1.354 (3) 1.537 (3) 1.526 (3) 1.526 (3) 1.533 (3) 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 1.390 (3) 1.397 (3) 1.385 (3) 0.9500 1.378 (3)
C44—H44B C44—H44C N5—H5 N6—H6A N7—H7A N8—H8A C45—N9 C45—C46 C45—H45A C45—H45B C46—O5 C46—H46A C46—H46B C47—O5 C47—C48 C47—H47A C47—H47B C48—O6 C48—H48A C48—H48B C49—O6 C49—C50 C49—H49A C49—H49B C50—N10 C50—H50A C50—H50B C51—N9 C51—C52 C51—H51A C51—H51B C52—O7 C52—H52A C52—H52B C53—O7 C53—C54 C53—H53A C53—H53B C54—O8 C54—H54A C54—H54B C55—O8 C55—C56 C55—H55A C55—H55B C56—N10 C56—H56A C56—H56B
0.9800 0.9800 0.8800 0.8800 0.8800 0.8800 1.467 (3) 1.499 (4) 0.9900 0.9900 1.430 (3) 0.9900 0.9900 1.418 (3) 1.496 (3) 0.9900 0.9900 1.421 (3) 0.9900 0.9900 1.420 (3) 1.509 (3) 0.9900 0.9900 1.468 (3) 0.9900 0.9900 1.465 (3) 1.504 (3) 0.9900 0.9900 1.424 (3) 0.9900 0.9900 1.423 (3) 1.495 (3) 0.9900 0.9900 1.417 (3) 0.9900 0.9900 1.423 (3) 1.504 (3) 0.9900 0.9900 1.465 (3) 0.9900 0.9900
sup-10
supporting information C14—H14A C15—C16 C15—H15A C16—C17 C16—H16A C17—N6 C18—O2 C18—N6 C18—C19 C19—C20 C19—C22 C19—C21 C20—H20I C20—H20J C20—H20K C21—H21A C21—H21B C21—H21C C22—H22A C22—H22B C22—H22C C23—C24 C23—C28 C24—C25 C24—H24A C25—C26 C25—H25A C26—C27 C26—H26A C27—C28 C27—H27A C28—N7 C29—O3 C29—N7 C29—C30
0.9500 1.383 (3) 0.9500 1.392 (3) 0.9500 1.404 (3) 1.213 (3) 1.368 (3) 1.534 (3) 1.526 (3) 1.530 (3) 1.534 (3) 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 1.394 (3) 1.400 (3) 1.387 (3) 0.9500 1.386 (3) 0.9500 1.379 (3) 0.9500 1.390 (3) 0.9500 1.412 (3) 1.217 (3) 1.366 (3) 1.533 (3)
C57—N9 C57—C58 C57—H57A C57—H57B C58—O9 C58—H58A C58—H58B C59—O9 C59—C60 C59—H59A C59—H59B C60—O10 C60—H60A C60—H60B C61—O10 C61—C62 C61—H61A C61—H61B C62—N10 C62—H62A C62—H62B C1S—C2S C1S—O1S C1S—H1SA C1S—H1SB C2S—C3S C2S—H2SA C2S—H2SB C3S—C4S C3S—H3SA C3S—H3SB C4S—O1S C4S—H4SA C4S—H4SB
1.468 (3) 1.501 (4) 0.9900 0.9900 1.415 (3) 0.9900 0.9900 1.421 (3) 1.484 (3) 0.9900 0.9900 1.425 (3) 0.9900 0.9900 1.421 (3) 1.504 (3) 0.9900 0.9900 1.471 (3) 0.9900 0.9900 1.397 (6) 1.532 (6) 0.9900 0.9900 1.431 (5) 0.9900 0.9900 1.365 (6) 0.9900 0.9900 1.515 (4) 0.9900 0.9900
O6—K1—O9 O6—K1—O10 O9—K1—O10 O6—K1—O5 O9—K1—O5 O10—K1—O5 O6—K1—O7 O9—K1—O7 O10—K1—O7 O5—K1—O7 O6—K1—O8 O9—K1—O8
128.21 (5) 92.10 (5) 59.68 (5) 59.56 (5) 92.09 (5) 115.02 (5) 121.37 (5) 103.64 (5) 142.25 (5) 98.09 (5) 98.72 (4) 127.48 (5)
C30—C32—H32A C30—C32—H32B H32A—C32—H32B C30—C32—H32C H32A—C32—H32C H32B—C32—H32C C30—C33—H33A C30—C33—H33B H33A—C33—H33B C30—C33—H33C H33A—C33—H33C H33B—C33—H33C
109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5
Acta Cryst. (2015). C71, 545-548
sup-11
supporting information O10—K1—O8 O5—K1—O8 O7—K1—O8 O6—K1—N9 O9—K1—N9 O10—K1—N9 O5—K1—N9 O7—K1—N9 O8—K1—N9 O6—K1—N10 O9—K1—N10 O10—K1—N10 O5—K1—N10 O7—K1—N10 O8—K1—N10 N9—K1—N10 N3—Mn1—N2 N3—Mn1—N1 N2—Mn1—N1 N3—Mn1—N4 N2—Mn1—N4 N1—Mn1—N4 N3—Mn1—Cl1 N2—Mn1—Cl1 N1—Mn1—Cl1 N4—Mn1—Cl1 N1—C101—C301 N1—C101—C201 C301—C101—C201 N1—C102—C302 N1—C102—C202 C302—C102—C202 N2—C103—C302 N2—C103—C203 C302—C103—C203 N2—C104—C303 N2—C104—C204 C303—C104—C204 N3—C105—C303 N3—C105—C205 C303—C105—C205 N3—C106—C304 N3—C106—C206 C304—C106—C206 N4—C107—C304 N4—C107—C207 C304—C107—C207 N4—C108—C301
Acta Cryst. (2015). C71, 545-548
102.11 (5) 136.39 (5) 59.13 (4) 119.46 (5) 60.27 (5) 119.45 (5) 60.37 (5) 61.36 (5) 119.76 (5) 60.97 (5) 120.19 (5) 61.12 (5) 120.16 (5) 117.76 (5) 59.36 (5) 179.11 (5) 84.88 (6) 145.77 (6) 85.58 (6) 85.92 (6) 146.39 (6) 84.10 (6) 103.37 (4) 104.04 (4) 110.84 (5) 109.53 (5) 125.28 (17) 109.59 (17) 125.13 (17) 125.76 (17) 109.71 (17) 124.52 (18) 125.18 (17) 109.51 (16) 125.30 (18) 125.26 (17) 109.27 (16) 125.36 (17) 125.06 (17) 109.55 (16) 125.36 (17) 125.42 (17) 109.56 (16) 125.01 (18) 125.45 (17) 109.44 (17) 125.09 (18) 125.32 (17)
C35—C34—C39 C35—C34—C304 C39—C34—C304 C36—C35—C34 C36—C35—H35A C34—C35—H35A C37—C36—C35 C37—C36—H36A C35—C36—H36A C36—C37—C38 C36—C37—H37A C38—C37—H37A C37—C38—C39 C37—C38—H38A C39—C38—H38A C38—C39—C34 C38—C39—N8 C34—C39—N8 O4—C40—N8 O4—C40—C41 N8—C40—C41 C44—C41—C42 C44—C41—C43 C42—C41—C43 C44—C41—C40 C42—C41—C40 C43—C41—C40 C41—C42—H42A C41—C42—H42B H42A—C42—H42B C41—C42—H42C H42A—C42—H42C H42B—C42—H42C C41—C43—H43A C41—C43—H43B H43A—C43—H43B C41—C43—H43C H43A—C43—H43C H43B—C43—H43C C41—C44—H44A C41—C44—H44B H44A—C44—H44B C41—C44—H44C H44A—C44—H44C H44B—C44—H44C C7—N5—C6 C7—N5—H5 C6—N5—H5
119.16 (18) 120.36 (17) 120.46 (17) 121.17 (19) 119.4 119.4 119.16 (19) 120.4 120.4 121.18 (19) 119.4 119.4 119.76 (19) 120.1 120.1 119.55 (19) 123.53 (19) 116.90 (18) 122.7 (2) 122.98 (19) 114.31 (18) 108.9 (2) 110.2 (2) 109.5 (2) 108.34 (19) 109.91 (19) 110.0 (2) 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 129.58 (18) 115.2 115.2
sup-12
supporting information N4—C108—C208 C301—C108—C208 C202—C201—C101 C202—C201—H20A C101—C201—H20A C201—C202—C102 C201—C202—H20B C102—C202—H20B C204—C203—C103 C204—C203—H20C C103—C203—H20C C203—C204—C104 C203—C204—H20D C104—C204—H20D C206—C205—C105 C206—C205—H20E C105—C205—H20E C205—C206—C106 C205—C206—H20F C106—C206—H20F C208—C207—C107 C208—C207—H20G C107—C207—H20G C207—C208—C108 C207—C208—H20H C108—C208—H20H C108—C301—C101 C108—C301—C1 C101—C301—C1 C102—C302—C103 C102—C302—C12 C103—C302—C12 C104—C303—C105 C104—C303—C23 C105—C303—C23 C107—C304—C106 C107—C304—C34 C106—C304—C34 C102—N1—C101 C102—N1—Mn1 C101—N1—Mn1 C103—N2—C104 C103—N2—Mn1 C104—N2—Mn1 C106—N3—C105 C106—N3—Mn1 C105—N3—Mn1 C107—N4—C108
Acta Cryst. (2015). C71, 545-548
109.51 (17) 125.18 (17) 106.96 (18) 126.5 126.5 107.10 (18) 126.5 126.5 107.25 (17) 126.4 126.4 106.94 (17) 126.5 126.5 107.20 (17) 126.4 126.4 106.89 (18) 126.6 126.6 107.04 (18) 126.5 126.5 107.11 (17) 126.4 126.4 125.56 (17) 118.54 (17) 115.90 (17) 126.51 (18) 114.88 (17) 118.60 (17) 126.15 (17) 117.32 (16) 116.34 (16) 126.70 (18) 117.32 (17) 115.99 (17) 106.61 (16) 124.53 (13) 125.62 (13) 107.01 (15) 125.51 (12) 125.56 (12) 106.81 (16) 125.36 (12) 126.35 (13) 106.89 (16)
C18—N6—C17 C18—N6—H6A C17—N6—H6A C29—N7—C28 C29—N7—H7A C28—N7—H7A C40—N8—C39 C40—N8—H8A C39—N8—H8A N9—C45—C46 N9—C45—H45A C46—C45—H45A N9—C45—H45B C46—C45—H45B H45A—C45—H45B O5—C46—C45 O5—C46—H46A C45—C46—H46A O5—C46—H46B C45—C46—H46B H46A—C46—H46B O5—C47—C48 O5—C47—H47A C48—C47—H47A O5—C47—H47B C48—C47—H47B H47A—C47—H47B O6—C48—C47 O6—C48—H48A C47—C48—H48A O6—C48—H48B C47—C48—H48B H48A—C48—H48B O6—C49—C50 O6—C49—H49A C50—C49—H49A O6—C49—H49B C50—C49—H49B H49A—C49—H49B N10—C50—C49 N10—C50—H50A C49—C50—H50A N10—C50—H50B C49—C50—H50B H50A—C50—H50B N9—C51—C52 N9—C51—H51A C52—C51—H51A
129.93 (18) 115.0 115.0 126.88 (17) 116.6 116.6 130.20 (18) 114.9 114.9 113.8 (2) 108.8 108.8 108.8 108.8 107.7 108.99 (19) 109.9 109.9 109.9 109.9 108.3 109.51 (18) 109.8 109.8 109.8 109.8 108.2 108.91 (18) 109.9 109.9 109.9 109.9 108.3 108.85 (18) 109.9 109.9 109.9 109.9 108.3 114.01 (18) 108.8 108.8 108.8 108.8 107.6 114.3 (2) 108.7 108.7
sup-13
supporting information C107—N4—Mn1 C108—N4—Mn1 C2—C1—C6 C2—C1—C301 C6—C1—C301 C3—C2—C1 C3—C2—H2A C1—C2—H2A C4—C3—C2 C4—C3—H3A C2—C3—H3A C3—C4—C5 C3—C4—H4A C5—C4—H4A C4—C5—C6 C4—C5—H5A C6—C5—H5A C5—C6—C1 C5—C6—N5 C1—C6—N5 O1—C7—N5 O1—C7—C8 N5—C7—C8 C11—C8—C9 C11—C8—C10 C9—C8—C10 C11—C8—C7 C9—C8—C7 C10—C8—C7 C8—C9—H9A C8—C9—H9B H9A—C9—H9B C8—C9—H9C H9A—C9—H9C H9B—C9—H9C C8—C10—H10A C8—C10—H10B H10A—C10—H10B C8—C10—H10C H10A—C10—H10C H10B—C10—H10C C8—C11—H11A C8—C11—H11B H11A—C11—H11B C8—C11—H11C H11A—C11—H11C H11B—C11—H11C C13—C12—C17
Acta Cryst. (2015). C71, 545-548
124.74 (13) 126.10 (13) 118.55 (18) 120.56 (18) 120.79 (18) 121.67 (19) 119.2 119.2 119.3 (2) 120.3 120.3 120.6 (2) 119.7 119.7 120.0 (2) 120.0 120.0 119.83 (19) 123.37 (19) 116.77 (18) 122.6 (2) 122.07 (19) 115.29 (18) 110.2 (2) 109.2 (2) 109.3 (2) 108.19 (19) 112.96 (18) 106.84 (18) 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 119.25 (19)
N9—C51—H51B C52—C51—H51B H51A—C51—H51B O7—C52—C51 O7—C52—H52A C51—C52—H52A O7—C52—H52B C51—C52—H52B H52A—C52—H52B O7—C53—C54 O7—C53—H53A C54—C53—H53A O7—C53—H53B C54—C53—H53B H53A—C53—H53B O8—C54—C53 O8—C54—H54A C53—C54—H54A O8—C54—H54B C53—C54—H54B H54A—C54—H54B O8—C55—C56 O8—C55—H55A C56—C55—H55A O8—C55—H55B C56—C55—H55B H55A—C55—H55B N10—C56—C55 N10—C56—H56A C55—C56—H56A N10—C56—H56B C55—C56—H56B H56A—C56—H56B N9—C57—C58 N9—C57—H57A C58—C57—H57A N9—C57—H57B C58—C57—H57B H57A—C57—H57B O9—C58—C57 O9—C58—H58A C57—C58—H58A O9—C58—H58B C57—C58—H58B H58A—C58—H58B O9—C59—C60 O9—C59—H59A C60—C59—H59A
108.7 108.7 107.6 109.41 (19) 109.8 109.8 109.8 109.8 108.2 109.08 (18) 109.9 109.9 109.9 109.9 108.3 109.21 (19) 109.8 109.8 109.8 109.8 108.3 108.75 (18) 109.9 109.9 109.9 109.9 108.3 114.08 (17) 108.7 108.7 108.7 108.7 107.6 114.5 (2) 108.6 108.6 108.6 108.6 107.6 108.72 (19) 109.9 109.9 109.9 109.9 108.3 108.50 (19) 110.0 110.0
sup-14
supporting information C13—C12—C302 C17—C12—C302 C14—C13—C12 C14—C13—H13A C12—C13—H13A C15—C14—C13 C15—C14—H14A C13—C14—H14A C14—C15—C16 C14—C15—H15A C16—C15—H15A C15—C16—C17 C15—C16—H16A C17—C16—H16A C16—C17—C12 C16—C17—N6 C12—C17—N6 O2—C18—N6 O2—C18—C19 N6—C18—C19 C20—C19—C22 C20—C19—C18 C22—C19—C18 C20—C19—C21 C22—C19—C21 C18—C19—C21 C19—C20—H20I C19—C20—H20J H20I—C20—H20J C19—C20—H20K H20I—C20—H20K H20J—C20—H20K C19—C21—H21A C19—C21—H21B H21A—C21—H21B C19—C21—H21C H21A—C21—H21C H21B—C21—H21C C19—C22—H22A C19—C22—H22B H22A—C22—H22B C19—C22—H22C H22A—C22—H22C H22B—C22—H22C C24—C23—C28 C24—C23—C303 C28—C23—C303 C25—C24—C23
Acta Cryst. (2015). C71, 545-548
120.38 (18) 120.08 (18) 120.5 (2) 119.8 119.8 119.7 (2) 120.2 120.2 121.0 (2) 119.5 119.5 119.4 (2) 120.3 120.3 120.1 (2) 123.0 (2) 116.81 (18) 123.0 (2) 123.9 (2) 113.14 (18) 109.16 (19) 108.48 (18) 109.50 (18) 109.90 (19) 110.32 (19) 109.45 (19) 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 118.38 (17) 119.46 (17) 122.16 (17) 121.59 (19)
O9—C59—H59B C60—C59—H59B H59A—C59—H59B O10—C60—C59 O10—C60—H60A C59—C60—H60A O10—C60—H60B C59—C60—H60B H60A—C60—H60B O10—C61—C62 O10—C61—H61A C62—C61—H61A O10—C61—H61B C62—C61—H61B H61A—C61—H61B N10—C62—C61 N10—C62—H62A C61—C62—H62A N10—C62—H62B C61—C62—H62B H62A—C62—H62B C51—N9—C45 C51—N9—C57 C45—N9—C57 C51—N9—K1 C45—N9—K1 C57—N9—K1 C56—N10—C50 C56—N10—C62 C50—N10—C62 C56—N10—K1 C50—N10—K1 C62—N10—K1 C47—O5—C46 C47—O5—K1 C46—O5—K1 C49—O6—C48 C49—O6—K1 C48—O6—K1 C53—O7—C52 C53—O7—K1 C52—O7—K1 C54—O8—C55 C54—O8—K1 C55—O8—K1 C58—O9—C59 C58—O9—K1 C59—O9—K1
110.0 110.0 108.4 110.10 (18) 109.6 109.6 109.6 109.6 108.2 108.49 (18) 110.0 110.0 110.0 110.0 108.4 113.32 (18) 108.9 108.9 108.9 108.9 107.7 109.76 (19) 110.11 (19) 110.12 (19) 108.72 (13) 110.34 (13) 107.74 (13) 110.12 (17) 109.19 (17) 109.66 (17) 111.32 (12) 107.93 (12) 108.60 (12) 111.04 (17) 114.11 (13) 115.94 (12) 111.65 (17) 117.87 (12) 117.93 (13) 110.61 (17) 115.37 (13) 113.64 (13) 111.31 (16) 114.16 (12) 117.13 (12) 111.98 (17) 120.80 (13) 115.74 (13)
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supporting information C25—C24—H24A C23—C24—H24A C26—C25—C24 C26—C25—H25A C24—C25—H25A C27—C26—C25 C27—C26—H26A C25—C26—H26A C26—C27—C28 C26—C27—H27A C28—C27—H27A C27—C28—C23 C27—C28—N7 C23—C28—N7 O3—C29—N7 O3—C29—C30 N7—C29—C30 C32—C30—C33 C32—C30—C29 C33—C30—C29 C32—C30—C31 C33—C30—C31 C29—C30—C31 C30—C31—H31A C30—C31—H31B H31A—C31—H31B C30—C31—H31C H31A—C31—H31C H31B—C31—H31C
Acta Cryst. (2015). C71, 545-548
119.2 119.2 119.05 (19) 120.5 120.5 120.51 (18) 119.7 119.7 120.40 (19) 119.8 119.8 120.07 (18) 121.63 (18) 118.23 (17) 122.21 (19) 120.73 (19) 117.06 (17) 110.0 (2) 114.59 (18) 106.69 (17) 109.68 (19) 108.89 (19) 106.82 (18) 109.5 109.5 109.5 109.5 109.5 109.5
C61—O10—C60 C61—O10—K1 C60—O10—K1 C2S—C1S—O1S C2S—C1S—H1SA O1S—C1S—H1SA C2S—C1S—H1SB O1S—C1S—H1SB H1SA—C1S—H1SB C1S—C2S—C3S C1S—C2S—H2SA C3S—C2S—H2SA C1S—C2S—H2SB C3S—C2S—H2SB H2SA—C2S—H2SB C4S—C3S—C2S C4S—C3S—H3SA C2S—C3S—H3SA C4S—C3S—H3SB C2S—C3S—H3SB H3SA—C3S—H3SB C3S—C4S—O1S C3S—C4S—H4SA O1S—C4S—H4SA C3S—C4S—H4SB O1S—C4S—H4SB H4SA—C4S—H4SB C4S—O1S—C1S
110.92 (16) 111.37 (12) 115.33 (13) 108.0 (3) 110.1 110.1 110.1 110.1 108.4 106.8 (4) 110.4 110.4 110.4 110.4 108.6 112.5 (4) 109.1 109.1 109.1 109.1 107.8 106.5 (3) 110.4 110.4 110.4 110.4 108.6 101.4 (4)
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Qiang Yu,a,b Xiangjun Li,b Diansheng Liua and Jianfeng Lib* a
Research Institute of Applied Chemistry, Shanxi University, Taiyuan, Shanxi 030006, People’s Republic of China, and College of Materials Science and Opto-electronic Technology, University of Chinese Academy of Sciences, YianQi Lake, HuaiRou District, Beijing 101408, People’s Republic of China. *Correspondence e-mail: [email protected] b
Received 28 April 2015 Accepted 15 May 2015 Edited by A. L. Spek, Utrecht University, The Netherlands Keywords: picket-fence porphyrin; cryptand222; manganese(II); potassium; crystal structure; 24-atom mean plane; near-planar conformation. CCDC reference: 1401463 Supporting information: this article has supporting information at journals.iucr.org/c
‘Picket-fence’ porphyrin compounds are used in the investigation of interactions of hemes with dioxygen, carbon monoxide, nitric monoxide and imidazole ligands. (Cryptand-222)potassium chlorido[meso-tetra( , , , -o-pivalamidophenyl)porphyrinato]manganese tetrahydrofuran monosolvate (cryptand-222 is 4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane), [K(C18H36N2O6)][Mn(C64H64N8O4)Cl]C4H8O or [K(222)][Mn(TpivPP)Cl]THF [systematic name for TpivPP: 5,10,15,20-tetrakis(2-tert-butanamidophenyl)porphyrin], is a fivecoordinate high-spin manganese(II) picket-fence porphyrin complex. It crystallizes with a potassium cation chelated inside a cryptand-222 molecule; the ˚ , respectively. average K—O and K—N distances are 2.83 (4) and 2.995 (13) A All four protecting tert-butyl pickets of the porphyrin are ordered. The porphyrin plane is nearly planar, as indicated by the atomic displacements and the dihedral angles between the mean planes of the pyrrole rings and the 24atom mean plane. The axial chloride ligand is located inside the molecular cavity on the hindered porphyrin side and the Mn—Cl bond is tilted slightly off the normal to the porphyrin plane by 3.68 (2) . The out-of-plane displacement of ˚, the metal centre relative to the 24-atom mean plane (24) is 0.7013 (4) A indicating a noticeable porphyrin core doming.
1. Introduction
# 2015 International Union of Crystallography
Acta Cryst. (2015). C71, 545–548
The picket-fence porphyrin model compound meso-tetra( , , , -o-pivalamidophenyl)porphyrin (denoted TpivPP) is a representative example used in the investigation of interactions of hemes with dioxygen, carbon monoxide, nitric monoxide and imidazole ligands. The first crystal structure of a picket-fence metalloporphyrin, namely [Fe(TpivPP)(1-MeIm)(O2)] (where 1-MeIm is 1-methylimidazole), was reported by Collman et al. (1975). Subsequently, many other iron and cobalt picket-fence porphyrin complexes were reported, e.g. four-coordinate [Co(TpivPP)] (Jene & Ibers, 2000), five-coordinate [K(222)][Fe(TpivPP)(OC6H5)] (Nasri et al., 1987), [Na(222)][Fe(TpivPP)(N3)] (Hachem et al., 2009), [Co(TpivPP)(2-MeHIm)] (2-MeHIm = 2-methylimidazole; Li et al., 2010), six-coordinate [Na(18C6)][Co(TpivPP)(SC6HF4)(O2)] (SC6HF4 = 2,3,5,6tetrafluorophenylthiolate and 18C6 = 18-crown-6; Doppelt et al., 1987), [Fe(TpivPP)(1-MeIm)2] (Li et al., 2008), [Co(TpivPP)(1-MeIm)(O2)] (Li et al., 2012) and [Fe(TpivPP)(1EtIm)(O2)] (1-EtIm = 1-ethylimidazole; Li et al., 2013). The geometric and electronic structures of three imidazole-ligated manganese(II) picket-fence porphyrin complexes have been reported recently, namely [Mn(TpivPP)(RIm)] (RIm = 1-MeIm, 1-EtIm and 2-MeHIm; Yu et al., 2015). We report here the structural properties of the five-coordinate picketfence porphyrin complex [K(222)][Mn(TpivPP)Cl]THF, (I). http://dx.doi.org/10.1107/S2053229615009304
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research papers 2. Experimental
Table 1
2.1. Synthesis and crystallization
Black block-shaped crystals were obtained from a frustrated attempt to obtain a manganese–peroxo porphyrin complex. [H2(TpivPP)], [MnIII(TpivPP)Cl] and [MnIII(TpivPP)]2O were prepared according to a local modification of a reported synthesis (Collman et al., 1975). [MnIII(TpivPP)]2O {10 mg, 9.33 10 3 mmol, with an [MnIII(TpivPP)Cl] impurity} was reduced in the presence of ethanethiol (1 ml). After a 48 h reaction time, the solution was evaporated to dryness under vacuum. The resulting purple solid was dried for an additional 30 min and then dissolved in tetrahydrofuran (THF, 2.5 ml). A twofold excess of kryptofix 222 and a fourfold excess potassium superoxide, KO2, were added to the solution. The mixture was stirred overnight and transferred to glass tubes which were layered with hexanes as nonsolvent. Crystals were collected after 30 d.
Experimental details. Crystal data Chemical formula Mr Crystal system, space group Temperature (K) ˚) a, b, c (A ( ) ˚ 3) V (A Z Radiation type (mm 1) Crystal size (mm) Data collection Diffractometer Absorption correction
[K(C18H36N2O6)][Mn(C64H64N8O4)Cl]C4H8O 1587.31 Monoclinic, P21/n 200 17.2598 (3), 21.2990 (3), 22.7585 (3) 96.378 (2) 8314.6 (2) 4 Mo K 0.31 0.20 0.20 0.10
Agilent Xcalibur (Eos, Gemini) diffractometer Multi-scan (CrysAlis PRO; Agilent, 2011) 0.984, 1.000 65981, 18558, 14238
Tmin, Tmax No. of measured, independent and observed [I > 2(I)] reflections Rint ˚ 1) (sin /)max (A
0.034 0.676
Refinement R[F 2 > 2(F 2)], wR(F 2), S No. of reflections No. of parameters No. of restraints H-atom treatment ˚ 3) max, min (e A
0.047, 0.113, 1.02 18558 992 5 H-atom parameters constrained 1.11, 0.97
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010).
of weak distance restraints. No attempt was made to model the disorder.
3. Results and discussion
2.2. Refinement
Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were placed in ˚ and C—H = 0.95, calculated positions, with N—H = 0.88 A ˚ 0.98 or 0.99 A for aryl, methyl or methine H atoms, respectively, and refined using a riding model with fixed isotropic displacement parameters, i.e. Uiso(H) = 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C,N) otherwise. The THF solvent molecule was found to be disordered and the C—C and C—O bond lengths appear unsatisfactory, even with the application
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[K(C18H36N2O6)][Mn(C64H64N8O4)Cl]C4H8O
In the title complex, [K(222)][Mn(TpivPP)Cl]THF, (I) (Fig. 1) (space group P21/n), the counter-ion to the negatively charged manganese(II) picket-fence porphyrinate is a potassium cation chelated inside a kryptofix 222 (4,7,13,16,21,24-hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane, 222) molecule. The six O and two N atoms of kryptofix 222 bind to the potassium cation through electrostatic interactions. The average K—O ˚ , respecand K—N distances are 2.83 (4) and 2.995 (13) A tively. The axial chloride ligand of the anion is located inside the molecular cavity on the hindered porphyrin side. The Mn—Cl ˚ and is tilted slightly [by 3.68 (2) ] bond lengths is 2.3704 (6) A from the normal to the porphyrin plane (Fig. 2). The oxidation state of manganese can differ, but the observed Mn—Cl bond length in (I) is almost the same as that of [MnIII(TPP)Cl] [TPP ˚ ; Tulinsky & Chen, 1977]. is tetraphenylporphyrin; 2.363 (3) A The reason for the similar bond lengths with different oxidation states could be that for high-spin manganese(II), the occupied dx2–y2 orbital has little interaction with the axial ligand (VanAtta et al., 1987). All four protecting tert-butyl pickets are ordered, similar to the five-coordinate analogues Acta Cryst. (2015). C71, 545–548
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Figure 2 Diagram illustrating the off-axis tilt of the axial ligand, the near-planar conformation and the core dome of the [Mn(TpivPP)Cl] anion. The dashed line indicates the position of the normal to the porphyrin plane.
The porphyrin atoms of the [Mn(TpivPP)Cl] anion presents a near-planar conformation. The displacements of the porphyrin meso-C and -C atoms from the mean plane are ˚ (Fig. 3). The near-planar conformation can also be 0.11 A seen by noting the dihedral angles between the 24-atom mean plane and the pyrrole-ring mean planes. For the pyrrole rings containing atoms N1, N2 and N4, the dihedral angles are 1.39 (8), 4.29 (8) and 3.07 (8) , respectively. The N3-pyrrole ring has the largest dihedral angle [5.26 (8) ]. This is consistent with the slightly shorter Mn—N3 bond length [2.1452 (16) ˚ ]. FeIII is versus 2.1538 (16), 2.1529 (15) and 2.1550 (16) A II isoelectronic with Mn and a near-planar conformation was found in the molecular structure of [Fe(TpivPP)Cl] (Dhifet et al., 2011). The dihedral angles between the mean planes of the pendent benzene rings and the 24-atom mean plane in
Figure 1 Displacement ellipsoid plots (50% probability level) of the components of [K(222)][Mn(TpivPP)Cl]THF, (I), i.e. (a) the [Mn(TpivPP)Cl] anion, (b) the [K(222)]+ cation and (c) the THF solvent molecule, showing the atom-labelling scheme.
[Fe(TpivPP)Cl] (Dhifet et al., 2011) and [K(222)][Fe(TpivPP)Cl] (Schappacher et al., 1983). Additional quantitative information on the structure of (I) is given in Fig. 3, which displays the displacements of each ˚ ) from the 24-atom porphyrin core atom (in units of 0.01 A mean plane. The average Mn—Np (Np is a porphyrin N atom) ˚ . The out-of-plane displacement of bond length is 2.152 (4) A the metal centre relative to the 24-atom mean plane (24) is ˚ . As can be seen in Fig. 2, the porphyrin core 0.7013 (4) A presents an obvious doming. The overall structural features of [Mn(TpivPP)Cl] are those expected for a high-spin MnII species (Kirner et al., 1977). Acta Cryst. (2015). C71, 545–548
Figure 3 Formal diagram of the porphyrinate core of [Mn(TpivPP)Cl] . Averaged ˚ ) and angles (in ) values of the chemically unique bond distances (in A are shown. The numbers in parentheses are the s.u. values calculated assuming that the averaged values were all drawn from the same ˚ ) of the population. The perpendicular displacements (in units of 0.01 A porphyrin core atoms from the 24-atom mean plane are also displayed. In the diagram, positive values of the displacement are towards the hindered porphyrin side. Yu et al.
[K(C18H36N2O6)][Mn(C64H64N8O4)Cl]C4H8O
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Acknowledgements The authors thank the CAS Hundred Talent Program and the National Natural Science Foundation of China (grant no. 21371167, to JL).
References
Figure 4
Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Collman, J. P., Gagne, R. R., Reed, C., Halbert, T. R., Lang, G. & Robinson, W. T. (1975). J. Am. Chem. Soc. 97, 1427–1439. Dhifet, M., Belkhiria, M. S., Daran, J.-C. & Nasri, H. (2011). Acta Cryst. E67, m460–m461. Doppelt, P., Fischer, J., Ricard, L. & Weiss, R. (1987). New J. Chem. 11, 357–364. Hachem, I., Belkhiria, M. S., Giorgi, M., Schulz, C. E. & Nasri, H. (2009). Polyhedron, 28, 954–958. Jene, P. G. & Ibers, J. A. (2000). Inorg. Chem. 39, 3823–3827. Kirner, J. F., Reed, C. A. & Scheidt, W. R. (1977). J. Am. Chem. Soc. 99, 2557–2563. Li, J., Nair, S. M., Noll, B. C., Schulz, C. E. & Scheidt, W. R. (2008). Inorg. Chem. 47, 3841–3850. Li, J., Noll, B. C., Oliver, A. G., Ferraudi, G., Lappin, A. G. & Scheidt, W. R. (2010). Inorg. Chem. 49, 2398–2406. Li, J., Noll, B. C., Oliver, A. G. & Scheidt, W. R. (2012). J. Am. Chem. Soc. 134, 10595–10606.
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View of the molecular packing of [K(222)][Mn(TpivPP)Cl]THF, (I), in the crystal. H atoms have been omitted for clarity.
Li, J., Noll, B. C., Oliver, A. G., Schulz, C. E. & Scheidt, W. R. (2013). J. Am. Chem. Soc. 135, 15627–15641. Nasri, H., Fischer, J., Weiss, R., Bill, E. & Trautwein, A. (1987). J. Am. Chem. Soc. 109, 2549–2550. Schappacher, M., Ricard, L., Weiss, R., Montiel-Montoya, R., Gonser, U., Bill, E. & Trautwein, A. (1983). Inorg. Chim. Acta, 78, L9–L12. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Sheldrick, G. M. (2015). Acta Cryst. C71, 3–8. Tulinsky, A. & Chen, B. M. L. (1977). J. Am. Chem. Soc. 99, 3647– 3651. VanAtta, R. B., Strouse, C. E., Hanson, L. K. & Valentine, J. S. (1987). J. Am. Chem. Soc. 109, 1425–1434. Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Yu, Q., Liu, Y. H., Liu, D. S. & Li, J. F. (2015). Dalton Trans. 44, 9382– 9390.
Acta Cryst. (2015). C71, 545–548
supporting information
supporting information Acta Cryst. (2015). C71, 545-548
[doi:10.1107/S2053229615009304]
Structural study of a manganese(II) `picket-fence′ porphyrin complex Qiang Yu, Xiangjun Li, Diansheng Liu and Jianfeng Li Computing details Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015) and publCIF (Westrip, 2010). (4,7,13,16,21,24-Hexaoxa-1,10-diazabicyclo[8.8.8]hexacosane)potassium chlorido[meso-5,10,15,20-tetrakis(2tert-butanamidophenyl)porphyrinato(2-)]manganese(II) tetrahydrofuran monosolvate Crystal data [K(C18H36N2O6)][MnCl(C64H64N8O4)]·C4H8O Mr = 1587.31 Monoclinic, P21/n a = 17.2598 (3) Å b = 21.2990 (3) Å c = 22.7585 (3) Å β = 96.378 (2)° V = 8314.6 (2) Å3 Z=4
F(000) = 3372 Dx = 1.268 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 17336 reflections θ = 3.0–28.7° µ = 0.31 mm−1 T = 200 K Block, black 0.20 × 0.20 × 0.10 mm
Data collection Agilent Xcalibur (Eos, Gemini) diffractometer Detector resolution: 16.2141 pixels mm-1 ω scans Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) Tmin = 0.984, Tmax = 1.000 65981 measured reflections
18558 independent reflections 14238 reflections with I > 2σ(I) Rint = 0.034 θmax = 28.7°, θmin = 3.0° h = −23→19 k = −28→27 l = −28→29
Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.047 wR(F2) = 0.113 S = 1.02 18558 reflections 992 parameters 5 restraints
Acta Cryst. (2015). C71, 545-548
Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ2(Fo2) + (0.0411P)2 + 8.2684P] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max = 0.003 Δρmax = 1.11 e Å−3 Δρmin = −0.97 e Å−3
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supporting information Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
Cl1 K1 Mn1 C101 C102 C103 C104 C105 C106 C107 C108 C201 H20A C202 H20B C203 H20C C204 H20D C205 H20E C206 H20F C207 H20G C208 H20H C301 C302 C303 C304 N1 N2 N3 N4
x
y
z
Uiso*/Ueq
0.97749 (3) 1.24267 (3) 1.03128 (2) 0.97515 (11) 0.89637 (11) 0.90017 (11) 0.98416 (11) 1.11881 (11) 1.19913 (11) 1.19430 (11) 1.10914 (12) 0.90592 (12) 0.8963 0.85766 (12) 0.8075 0.86796 (12) 0.8198 0.91904 (12) 0.9134 1.19125 (12) 1.2020 1.24077 (12) 1.2929 1.23004 (12) 1.2807 1.17776 (12) 1.1848 1.04113 (12) 0.86537 (11) 1.05262 (11) 1.23065 (11) 0.96709 (9) 0.97041 (9) 1.12525 (9) 1.12068 (9)
0.96273 (3) 0.83486 (2) 0.93078 (2) 0.79137 (9) 0.85782 (9) 0.97245 (9) 1.04917 (9) 1.05626 (9) 0.98915 (9) 0.87459 (9) 0.79850 (9) 0.75679 (9) 0.7135 0.79761 (9) 0.7885 1.02762 (9) 1.0301 1.07491 (9) 1.1171 1.08912 (9) 1.1317 1.04800 (9) 1.0561 0.81770 (9) 0.8139 0.77105 (9) 0.7282 0.76548 (9) 0.91263 (9) 1.08175 (8) 0.93356 (9) 0.85288 (7) 0.98696 (7) 0.99570 (7) 0.86154 (7)
0.82146 (2) 0.54958 (2) 0.73482 (2) 0.71035 (8) 0.66039 (8) 0.63512 (8) 0.65560 (8) 0.70925 (8) 0.75751 (8) 0.78299 (8) 0.76439 (8) 0.68826 (9) 0.6943 0.65756 (9) 0.6377 0.60465 (9) 0.5802 0.61741 (8) 0.6039 0.72555 (8) 0.7170 0.75514 (9) 0.7713 0.80801 (9) 0.8287 0.79640 (9) 0.8072 0.74344 (8) 0.63264 (8) 0.67595 (8) 0.78361 (8) 0.69335 (7) 0.66582 (7) 0.72941 (7) 0.75741 (7)
0.02712 (12) 0.02032 (10) 0.01402 (7) 0.0165 (4) 0.0167 (4) 0.0150 (4) 0.0147 (4) 0.0151 (4) 0.0157 (4) 0.0169 (4) 0.0169 (4) 0.0215 (4) 0.026* 0.0213 (4) 0.026* 0.0188 (4) 0.023* 0.0181 (4) 0.022* 0.0179 (4) 0.021* 0.0185 (4) 0.022* 0.0205 (4) 0.025* 0.0207 (4) 0.025* 0.0165 (4) 0.0155 (4) 0.0146 (4) 0.0162 (4) 0.0155 (3) 0.0143 (3) 0.0146 (3) 0.0163 (3)
Acta Cryst. (2015). C71, 545-548
sup-2
supporting information C1 C2 H2A C3 H3A C4 H4A C5 H5A C6 C7 C8 C9 H9A H9B H9C C10 H10A H10B H10C C11 H11A H11B H11C C12 C13 H13A C14 H14A C15 H15A C16 H16A C17 C18 C19 C20 H20I H20J H20K C21 H21A H21B H21C C22 H22A H22B H22C
1.03725 (11) 1.04129 (12) 1.0494 1.03375 (14) 1.0371 1.02134 (14) 1.0156 1.01716 (14) 1.0090 1.02489 (13) 1.01490 (12) 1.01983 (14) 0.98399 (16) 0.9300 1.0142 0.9848 1.10654 (15) 1.1330 1.1122 1.1299 0.97894 (18) 1.0024 0.9846 0.9235 0.78675 (12) 0.77998 (13) 0.8255 0.70741 (14) 0.7032 0.64133 (13) 0.5916 0.64638 (13) 0.6004 0.71942 (12) 0.67842 (12) 0.71798 (12) 0.65501 (14) 0.6197 0.6254 0.6794 0.76366 (14) 0.8040 0.7280 0.7882 0.77277 (14) 0.8133 0.7971 0.7430
Acta Cryst. (2015). C71, 545-548
0.69649 (9) 0.65275 (9) 0.6669 0.58907 (10) 0.5599 0.56839 (10) 0.5248 0.61058 (10) 0.5959 0.67494 (9) 0.71404 (10) 0.77528 (10) 0.83125 (11) 0.8214 0.8402 0.8681 0.78806 (12) 0.7948 0.8256 0.7520 0.76489 (13) 0.7289 0.8025 0.7566 0.90490 (9) 0.88326 (10) 0.8773 0.87030 (10) 0.8544 0.88063 (10) 0.8726 0.90258 (10) 0.9102 0.91347 (10) 0.92934 (10) 0.93555 (10) 0.93514 (13) 0.9708 0.8959 0.9385 0.99744 (11) 0.9974 1.0327 1.0018 0.87984 (11) 0.8799 0.8833 0.8406
0.75621 (9) 0.71149 (9) 0.6731 0.72143 (10) 0.6903 0.77712 (10) 0.7841 0.82283 (10) 0.8611 0.81275 (9) 0.91515 (9) 0.95107 (9) 0.91606 (11) 0.9008 0.8830 0.9420 0.96934 (12) 0.9339 0.9943 0.9914 1.00635 (11) 1.0284 1.0313 0.9948 0.59845 (9) 0.54047 (9) 0.5212 0.51064 (10) 0.4714 0.53809 (10) 0.5172 0.59557 (10) 0.6139 0.62637 (9) 0.72783 (10) 0.79131 (10) 0.83337 (11) 0.8244 0.8285 0.8742 0.79764 (11) 0.7705 0.7881 0.8384 0.80564 (11) 0.7787 0.8465 0.8008
0.0180 (4) 0.0213 (4) 0.026* 0.0268 (5) 0.032* 0.0296 (5) 0.036* 0.0292 (5) 0.035* 0.0224 (4) 0.0219 (4) 0.0258 (5) 0.0362 (6) 0.054* 0.054* 0.054* 0.0392 (6) 0.059* 0.059* 0.059* 0.0427 (7) 0.064* 0.064* 0.064* 0.0184 (4) 0.0231 (4) 0.028* 0.0278 (5) 0.033* 0.0288 (5) 0.035* 0.0274 (5) 0.033* 0.0215 (4) 0.0235 (4) 0.0246 (5) 0.0349 (6) 0.052* 0.052* 0.052* 0.0327 (5) 0.049* 0.049* 0.049* 0.0311 (5) 0.047* 0.047* 0.047*
sup-3
supporting information C23 C24 H24A C25 H25A C26 H26A C27 H27A C28 C29 C30 C31 H31A H31B H31C C32 H32A H32B H32C C33 H33A H33B H33C C34 C35 H35A C36 H36A C37 H37A C38 H38A C39 C40 C41 C42 H42A H42B H42C C43 H43A H43B H43C C44 H44A H44B H44C
1.05898 (11) 1.10624 (12) 1.1332 1.11491 (12) 1.1470 1.07609 (12) 1.0819 1.02905 (12) 1.0030 1.01956 (11) 0.91079 (12) 0.87020 (13) 0.86661 (15) 0.8408 0.8371 0.9196 0.91032 (15) 0.9635 0.8810 0.9123 0.78705 (14) 0.7617 0.7888 0.7575 1.31150 (11) 1.37498 (12) 1.3667 1.45029 (12) 1.4934 1.46185 (12) 1.5133 1.39985 (12) 1.4088 1.32409 (12) 1.25169 (13) 1.16770 (13) 1.12256 (15) 1.1206 1.1487 1.0694 1.12716 (16) 1.1259 1.0738 1.1559 1.17019 (17) 1.1990 1.1169 1.1962
Acta Cryst. (2015). C71, 545-548
1.14865 (9) 1.16328 (9) 1.1305 1.22454 (10) 1.2336 1.27234 (9) 1.3145 1.25913 (9) 1.2923 1.19760 (9) 1.21558 (10) 1.18985 (10) 1.24381 (11) 1.2801 1.2304 1.2555 1.13319 (12) 1.1447 1.1198 1.0987 1.17247 (12) 1.2091 1.1381 1.1591 0.93851 (9) 0.91747 (9) 0.8988 0.92319 (9) 0.9095 0.94905 (10) 0.9522 0.97045 (10) 0.9883 0.96565 (9) 1.01610 (10) 1.02912 (11) 0.96738 (12) 0.9471 0.9396 0.9759 1.07239 (13) 1.0520 1.0808 1.1120 1.06009 (15) 1.0997 1.0684 1.0321
0.65651 (8) 0.61260 (9) 0.5952 0.59375 (9) 0.5635 0.61968 (9) 0.6073 0.66328 (9) 0.6809 0.68158 (8) 0.74252 (9) 0.79408 (9) 0.83828 (10) 0.8181 0.8704 0.8545 0.82526 (11) 0.8413 0.8575 0.7969 0.76875 (11) 0.7488 0.7403 0.8009 0.81507 (8) 0.78820 (9) 0.7501 0.81594 (9) 0.7967 0.87173 (10) 0.8912 0.89987 (9) 0.9383 0.87165 (9) 0.94914 (9) 0.96172 (10) 0.96264 (12) 0.9239 0.9929 0.9717 0.91395 (13) 0.8753 0.9226 0.9135 1.02221 (13) 1.0221 1.0312 1.0523
0.0150 (4) 0.0200 (4) 0.024* 0.0224 (4) 0.027* 0.0213 (4) 0.026* 0.0200 (4) 0.024* 0.0161 (4) 0.0214 (4) 0.0230 (4) 0.0334 (5) 0.050* 0.050* 0.050* 0.0358 (6) 0.054* 0.054* 0.054* 0.0353 (6) 0.053* 0.053* 0.053* 0.0167 (4) 0.0194 (4) 0.023* 0.0213 (4) 0.026* 0.0229 (4) 0.027* 0.0229 (4) 0.028* 0.0204 (4) 0.0235 (4) 0.0288 (5) 0.0410 (6) 0.062* 0.062* 0.062* 0.0455 (7) 0.068* 0.068* 0.068* 0.0512 (8) 0.077* 0.077* 0.077*
sup-4
supporting information N5 H5 N6 H6A N7 H7A N8 H8A O1 O2 O3 O4 C45 H45A H45B C46 H46A H46B C47 H47A H47B C48 H48A H48B C49 H49A H49B C50 H50A H50B C51 H51A H51B C52 H52A H52B C53 H53A H53B C54 H54A H54B C55 H55A H55B C56 H56A H56B
1.01866 (12) 1.0169 0.72999 (10) 0.7770 0.97367 (10) 0.9870 1.25761 (10) 1.2128 1.01091 (11) 0.60861 (9) 0.88698 (10) 1.30841 (10) 1.10066 (15) 1.0632 1.0736 1.16806 (16) 1.2073 1.1499 1.26249 (14) 1.2418 1.3048 1.29397 (14) 1.3343 1.2516 1.36470 (14) 1.3255 1.3994 1.41170 (13) 1.4486 1.4429 1.15582 (15) 1.1901 1.1127 1.20183 (15) 1.1700 1.2157 1.31928 (14) 1.3333 1.2910 1.39149 (13) 1.4284 1.4172 1.43878 (13) 1.4662 1.4749 1.41402 (13) 1.3855 1.4612
Acta Cryst. (2015). C71, 545-548
0.72094 (8) 0.7600 0.93052 (9) 0.9440 1.18289 (8) 1.1491 0.98548 (9) 0.9767 0.66306 (7) 0.92353 (8) 1.26286 (8) 1.03157 (8) 0.71835 (12) 0.7505 0.6773 0.71585 (11) 0.6853 0.7020 0.77805 (12) 0.7640 0.7490 0.84330 (12) 0.8448 0.8726 0.92053 (11) 0.9543 0.9214 0.93084 (11) 0.8954 0.9697 0.67707 (11) 0.6554 0.6480 0.69025 (12) 0.7154 0.6503 0.73152 (12) 0.6900 0.7554 0.76615 (11) 0.7675 0.7443 0.86426 (10) 0.8460 0.8640 0.93042 (10) 0.9474 0.9565
0.85641 (8) 0.8436 0.68634 (8) 0.6992 0.72734 (7) 0.7483 0.89729 (8) 0.8765 0.93834 (7) 0.71525 (7) 0.71641 (8) 0.98270 (7) 0.47510 (11) 0.4581 0.4723 0.43892 (11) 0.4564 0.3982 0.40014 (10) 0.3600 0.4155 0.39747 (9) 0.3698 0.3830 0.45440 (10) 0.4467 0.4226 0.51358 (10) 0.5214 0.5116 0.56856 (11) 0.5429 0.5748 0.62732 (11) 0.6522 0.6480 0.67259 (10) 0.6901 0.7008 0.66123 (10) 0.6978 0.6303 0.63496 (10) 0.6030 0.6719 0.61939 (10) 0.6513 0.6176
0.0294 (4) 0.035* 0.0280 (4) 0.034* 0.0185 (3) 0.022* 0.0259 (4) 0.031* 0.0340 (4) 0.0342 (4) 0.0380 (4) 0.0359 (4) 0.0342 (6) 0.041* 0.041* 0.0345 (6) 0.041* 0.041* 0.0321 (5) 0.038* 0.038* 0.0307 (5) 0.037* 0.037* 0.0290 (5) 0.035* 0.035* 0.0270 (5) 0.032* 0.032* 0.0347 (6) 0.042* 0.042* 0.0346 (6) 0.042* 0.042* 0.0317 (5) 0.038* 0.038* 0.0285 (5) 0.034* 0.034* 0.0260 (5) 0.031* 0.031* 0.0272 (5) 0.033* 0.033*
sup-5
supporting information C57 H57A H57B C58 H58A H58B C59 H59A H59B C60 H60A H60B C61 H61A H61B C62 H62A H62B N9 N10 O5 O6 O7 O8 O9 O10 C1S H1SA H1SB C2S H2SA H2SB C3S H3SA H3SB C4S H4SA H4SB O1S
1.05497 (14) 1.0684 1.0119 1.02657 (14) 1.0129 0.9794 1.06258 (13) 1.0100 1.0603 1.11973 (14) 1.1022 1.1232 1.25191 (14) 1.2627 1.2330 1.32497 (14) 1.3116 1.3614 1.12303 (11) 1.36440 (10) 1.20222 (9) 1.32680 (9) 1.27090 (9) 1.37130 (8) 1.08639 (9) 1.19450 (9) 0.8305 (3) 0.7983 0.8485 0.7867 (2) 0.7939 0.7306 0.8140 (3) 0.7700 0.8330 0.8726 (3) 0.9156 0.8530 0.9006 (3)
0.75530 (12) 0.7560 0.7249 0.81928 (12) 0.8196 0.8303 0.92577 (11) 0.9337 0.9317 0.97002 (11) 1.0137 0.9628 0.99785 (11) 0.9801 1.0414 0.99754 (10) 1.0097 1.0294 0.73303 (9) 0.93620 (8) 0.77693 (7) 0.86139 (7) 0.72376 (7) 0.82805 (7) 0.86347 (7) 0.96118 (7) 0.6000 (2) 0.5620 0.6002 0.6539 (2) 0.6852 0.6433 0.6784 (3) 0.6801 0.7218 0.64305 (16) 0.6704 0.6184 0.59968 (19)
0.56505 (12) 0.6085 0.5561 0.54515 (11) 0.5017 0.5640 0.54597 (10) 0.5579 0.5027 0.57695 (11) 0.5690 0.6201 0.59118 (11) 0.6314 0.5946 0.56081 (11) 0.5189 0.5796 0.53768 (8) 0.56310 (8) 0.43767 (7) 0.45499 (6) 0.61824 (6) 0.64252 (6) 0.56131 (7) 0.55722 (7) 0.59808 (19) 0.5890 0.6409 0.58276 (17) 0.6151 0.5754 0.5303 (3) 0.4985 0.5379 0.51159 (13) 0.5016 0.4761 0.56226 (17)
0.0355 (6) 0.043* 0.043* 0.0344 (6) 0.041* 0.041* 0.0292 (5) 0.035* 0.035* 0.0322 (5) 0.039* 0.039* 0.0308 (5) 0.037* 0.037* 0.0296 (5) 0.035* 0.035* 0.0279 (4) 0.0222 (4) 0.0281 (3) 0.0275 (3) 0.0270 (3) 0.0246 (3) 0.0286 (3) 0.0266 (3) 0.107 (2) 0.129* 0.129* 0.0717 (11) 0.086* 0.086* 0.148 (3) 0.178* 0.178* 0.0720 (12) 0.086* 0.086* 0.1484 (17)
Atomic displacement parameters (Å2)
Cl1 K1 Mn1 C101 C102
U11
U22
U33
U12
U13
U23
0.0302 (3) 0.0197 (2) 0.01294 (14) 0.0174 (10) 0.0145 (9)
0.0293 (3) 0.0203 (2) 0.01214 (14) 0.0139 (9) 0.0157 (9)
0.0231 (2) 0.0209 (2) 0.01662 (14) 0.0185 (9) 0.0201 (9)
0.0045 (2) 0.00031 (17) 0.00003 (11) −0.0004 (8) −0.0019 (8)
0.0085 (2) 0.00216 (17) 0.00004 (11) 0.0036 (8) 0.0034 (8)
−0.0006 (2) −0.00032 (17) 0.00194 (11) 0.0005 (7) −0.0016 (8)
Acta Cryst. (2015). C71, 545-548
sup-6
supporting information C103 C104 C105 C106 C107 C108 C201 C202 C203 C204 C205 C206 C207 C208 C301 C302 C303 C304 N1 N2 N3 N4 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15 C16 C17 C18 C19 C20 C21 C22 C23 C24 C25 C26
0.0130 (9) 0.0156 (9) 0.0163 (9) 0.0144 (9) 0.0160 (10) 0.0183 (10) 0.0196 (10) 0.0187 (10) 0.0156 (10) 0.0182 (10) 0.0204 (10) 0.0157 (10) 0.0179 (10) 0.0219 (11) 0.0197 (10) 0.0132 (9) 0.0166 (10) 0.0128 (9) 0.0152 (8) 0.0131 (8) 0.0141 (8) 0.0153 (8) 0.0165 (10) 0.0229 (11) 0.0329 (13) 0.0394 (14) 0.0418 (14) 0.0269 (11) 0.0205 (11) 0.0321 (12) 0.0515 (16) 0.0385 (15) 0.0625 (19) 0.0163 (10) 0.0230 (11) 0.0322 (13) 0.0219 (11) 0.0175 (11) 0.0175 (10) 0.0157 (10) 0.0156 (10) 0.0212 (12) 0.0293 (13) 0.0251 (12) 0.0140 (9) 0.0194 (10) 0.0200 (11) 0.0194 (10)
Acta Cryst. (2015). C71, 545-548
0.0161 (9) 0.0138 (9) 0.0138 (9) 0.0158 (9) 0.0168 (9) 0.0142 (9) 0.0164 (10) 0.0170 (10) 0.0187 (10) 0.0150 (9) 0.0128 (9) 0.0189 (10) 0.0188 (10) 0.0149 (9) 0.0134 (9) 0.0163 (9) 0.0129 (9) 0.0191 (10) 0.0133 (8) 0.0131 (8) 0.0133 (8) 0.0146 (8) 0.0133 (9) 0.0186 (10) 0.0163 (10) 0.0137 (10) 0.0178 (10) 0.0159 (10) 0.0229 (11) 0.0227 (11) 0.0245 (12) 0.0274 (12) 0.0408 (15) 0.0130 (9) 0.0205 (10) 0.0243 (11) 0.0281 (12) 0.0278 (12) 0.0190 (10) 0.0202 (10) 0.0267 (11) 0.0489 (15) 0.0304 (12) 0.0334 (13) 0.0133 (9) 0.0170 (10) 0.0212 (10) 0.0140 (9)
0.0161 (9) 0.0153 (9) 0.0154 (9) 0.0167 (9) 0.0178 (9) 0.0182 (9) 0.0282 (11) 0.0275 (11) 0.0215 (10) 0.0207 (9) 0.0203 (9) 0.0204 (9) 0.0240 (10) 0.0250 (10) 0.0168 (9) 0.0172 (9) 0.0149 (8) 0.0164 (9) 0.0179 (8) 0.0167 (8) 0.0159 (7) 0.0186 (8) 0.0240 (10) 0.0230 (10) 0.0313 (11) 0.0356 (12) 0.0291 (11) 0.0248 (10) 0.0214 (10) 0.0226 (10) 0.0325 (12) 0.0494 (15) 0.0265 (12) 0.0249 (10) 0.0249 (10) 0.0242 (11) 0.0330 (12) 0.0358 (12) 0.0272 (10) 0.0347 (12) 0.0321 (11) 0.0358 (13) 0.0390 (13) 0.0345 (12) 0.0168 (9) 0.0239 (10) 0.0262 (11) 0.0293 (11)
0.0007 (7) 0.0011 (7) 0.0007 (7) −0.0001 (7) 0.0028 (8) 0.0018 (8) −0.0033 (8) −0.0041 (8) 0.0011 (8) 0.0019 (8) −0.0008 (8) −0.0026 (8) 0.0033 (8) 0.0044 (8) 0.0008 (8) −0.0015 (7) 0.0000 (7) 0.0010 (8) −0.0006 (6) −0.0003 (6) 0.0005 (6) 0.0004 (6) 0.0012 (8) −0.0005 (8) 0.0007 (9) 0.0018 (9) 0.0010 (10) 0.0019 (8) −0.0008 (8) 0.0007 (9) 0.0100 (11) −0.0037 (11) −0.0072 (13) −0.0018 (8) −0.0009 (9) −0.0062 (9) −0.0073 (9) −0.0038 (9) −0.0020 (8) −0.0019 (8) −0.0018 (9) −0.0017 (11) −0.0079 (10) 0.0027 (10) −0.0013 (7) 0.0003 (8) −0.0030 (8) −0.0030 (8)
0.0020 (7) 0.0043 (7) 0.0022 (7) 0.0016 (7) 0.0018 (8) 0.0023 (8) 0.0013 (8) −0.0011 (8) −0.0014 (8) 0.0005 (8) 0.0014 (8) −0.0002 (8) −0.0011 (8) 0.0004 (8) 0.0038 (8) 0.0018 (7) 0.0038 (7) 0.0003 (7) 0.0009 (6) 0.0018 (6) −0.0003 (6) 0.0007 (6) 0.0013 (8) 0.0046 (8) 0.0043 (10) 0.0041 (10) 0.0091 (10) 0.0043 (9) −0.0010 (8) 0.0023 (9) 0.0042 (11) −0.0052 (12) 0.0131 (12) −0.0027 (8) −0.0007 (9) −0.0084 (9) −0.0113 (9) −0.0019 (9) −0.0012 (8) 0.0035 (9) 0.0049 (9) 0.0084 (10) 0.0058 (10) 0.0019 (10) −0.0025 (7) 0.0035 (8) 0.0034 (8) −0.0034 (8)
0.0000 (7) 0.0001 (7) −0.0009 (7) −0.0006 (7) 0.0012 (8) 0.0024 (8) 0.0014 (8) 0.0011 (8) 0.0028 (8) 0.0032 (8) −0.0012 (8) −0.0013 (8) 0.0043 (8) 0.0054 (8) 0.0021 (7) 0.0004 (7) −0.0012 (7) −0.0007 (8) 0.0017 (6) 0.0012 (6) 0.0011 (6) 0.0020 (6) 0.0028 (8) 0.0021 (8) −0.0003 (9) 0.0044 (9) 0.0078 (9) 0.0023 (8) 0.0051 (8) 0.0020 (9) −0.0010 (10) −0.0052 (11) −0.0025 (11) 0.0050 (8) 0.0028 (9) 0.0022 (9) 0.0087 (10) 0.0078 (10) 0.0028 (8) −0.0012 (9) −0.0051 (9) −0.0040 (11) −0.0090 (11) 0.0002 (10) 0.0005 (7) −0.0002 (8) 0.0057 (9) 0.0058 (8)
sup-7
supporting information C27 C28 C29 C30 C31 C32 C33 C34 C35 C36 C37 C38 C39 C40 C41 C42 C43 C44 N5 N6 N7 N8 O1 O2 O3 O4 C45 C46 C47 C48 C49 C50 C51 C52 C53 C54 C55 C56 C57 C58 C59 C60 C61 C62 N9 N10 O5 O6
0.0204 (10) 0.0150 (9) 0.0204 (11) 0.0246 (11) 0.0375 (14) 0.0410 (15) 0.0312 (13) 0.0149 (10) 0.0193 (10) 0.0155 (10) 0.0141 (10) 0.0186 (10) 0.0173 (10) 0.0252 (11) 0.0236 (12) 0.0344 (14) 0.0304 (14) 0.0366 (16) 0.0519 (13) 0.0138 (9) 0.0206 (9) 0.0140 (9) 0.0537 (11) 0.0137 (8) 0.0376 (10) 0.0265 (9) 0.0334 (13) 0.0454 (15) 0.0329 (13) 0.0297 (13) 0.0262 (12) 0.0203 (11) 0.0360 (14) 0.0338 (14) 0.0334 (13) 0.0276 (12) 0.0196 (11) 0.0237 (11) 0.0240 (12) 0.0200 (12) 0.0225 (11) 0.0284 (12) 0.0306 (13) 0.0277 (12) 0.0274 (10) 0.0193 (9) 0.0302 (9) 0.0274 (8)
Acta Cryst. (2015). C71, 545-548
0.0131 (9) 0.0147 (9) 0.0203 (10) 0.0224 (10) 0.0326 (13) 0.0343 (13) 0.0435 (15) 0.0148 (9) 0.0153 (9) 0.0161 (10) 0.0227 (10) 0.0290 (11) 0.0204 (10) 0.0203 (10) 0.0305 (12) 0.0402 (15) 0.0450 (16) 0.068 (2) 0.0139 (8) 0.0405 (11) 0.0136 (8) 0.0406 (11) 0.0240 (8) 0.0492 (11) 0.0329 (9) 0.0440 (10) 0.0322 (13) 0.0264 (12) 0.0400 (14) 0.0440 (14) 0.0328 (12) 0.0277 (11) 0.0262 (12) 0.0335 (13) 0.0353 (13) 0.0290 (12) 0.0312 (12) 0.0267 (11) 0.0399 (14) 0.0457 (15) 0.0366 (13) 0.0338 (13) 0.0222 (11) 0.0177 (10) 0.0271 (10) 0.0192 (9) 0.0285 (8) 0.0342 (9)
0.0258 (10) 0.0177 (9) 0.0236 (10) 0.0227 (10) 0.0315 (12) 0.0342 (13) 0.0317 (12) 0.0195 (9) 0.0236 (10) 0.0325 (11) 0.0306 (11) 0.0198 (10) 0.0233 (10) 0.0249 (10) 0.0326 (12) 0.0516 (16) 0.0607 (18) 0.0502 (17) 0.0240 (9) 0.0294 (10) 0.0216 (8) 0.0224 (9) 0.0226 (8) 0.0396 (9) 0.0466 (10) 0.0355 (9) 0.0352 (13) 0.0301 (12) 0.0233 (11) 0.0186 (10) 0.0294 (11) 0.0341 (12) 0.0415 (14) 0.0360 (13) 0.0256 (11) 0.0273 (11) 0.0265 (11) 0.0308 (11) 0.0436 (14) 0.0378 (13) 0.0294 (11) 0.0362 (12) 0.0395 (13) 0.0438 (13) 0.0285 (10) 0.0282 (9) 0.0256 (8) 0.0211 (7)
0.0004 (8) −0.0012 (7) 0.0022 (8) 0.0022 (9) 0.0003 (11) 0.0090 (11) −0.0092 (11) −0.0001 (7) 0.0011 (8) 0.0024 (8) −0.0015 (8) −0.0041 (9) 0.0003 (8) 0.0003 (9) −0.0012 (9) −0.0091 (12) 0.0114 (12) −0.0015 (14) 0.0028 (8) −0.0066 (8) 0.0028 (7) 0.0002 (8) −0.0088 (8) −0.0033 (7) 0.0188 (8) −0.0007 (8) −0.0088 (11) −0.0012 (11) 0.0089 (11) 0.0058 (11) 0.0009 (10) −0.0021 (9) −0.0094 (10) −0.0086 (11) 0.0005 (11) 0.0028 (10) −0.0022 (9) −0.0031 (9) −0.0104 (10) −0.0047 (10) 0.0094 (10) 0.0083 (10) 0.0051 (10) −0.0020 (9) −0.0046 (8) 0.0012 (7) 0.0019 (7) −0.0034 (7)
−0.0010 (8) −0.0019 (7) 0.0027 (8) 0.0060 (9) 0.0093 (10) 0.0140 (11) 0.0059 (10) −0.0015 (8) 0.0025 (8) 0.0036 (8) −0.0030 (8) −0.0034 (8) 0.0010 (8) 0.0019 (9) 0.0041 (9) 0.0184 (12) 0.0040 (13) 0.0110 (13) 0.0109 (9) 0.0017 (7) 0.0039 (7) −0.0019 (7) −0.0039 (7) 0.0029 (7) 0.0192 (8) −0.0035 (7) −0.0045 (11) −0.0022 (11) 0.0032 (10) 0.0042 (9) 0.0094 (9) 0.0081 (9) 0.0025 (11) 0.0021 (11) −0.0002 (10) −0.0047 (9) −0.0010 (9) 0.0018 (9) 0.0083 (11) 0.0039 (10) 0.0076 (9) 0.0114 (10) 0.0041 (10) 0.0062 (10) 0.0002 (8) 0.0040 (7) 0.0031 (7) 0.0027 (6)
−0.0010 (8) 0.0002 (8) −0.0010 (8) −0.0008 (9) −0.0072 (10) 0.0123 (11) 0.0004 (11) 0.0044 (8) 0.0025 (8) 0.0048 (9) 0.0074 (9) 0.0021 (9) 0.0036 (8) −0.0004 (9) −0.0103 (10) −0.0085 (13) 0.0009 (14) −0.0302 (15) 0.0049 (7) −0.0059 (9) 0.0029 (7) −0.0065 (8) 0.0081 (7) −0.0027 (8) 0.0166 (8) −0.0168 (8) −0.0056 (10) −0.0085 (10) −0.0082 (10) −0.0006 (10) 0.0065 (10) 0.0013 (10) 0.0032 (11) 0.0131 (11) 0.0110 (10) 0.0069 (9) −0.0021 (9) −0.0070 (10) 0.0009 (11) −0.0047 (11) −0.0032 (10) −0.0094 (10) −0.0103 (10) −0.0023 (10) −0.0004 (8) −0.0017 (7) −0.0063 (7) 0.0021 (6)
sup-8
supporting information O7 O8 O9 O10 C1S C2S C3S C4S O1S
0.0259 (8) 0.0184 (7) 0.0197 (8) 0.0245 (8) 0.173 (5) 0.047 (2) 0.069 (3) 0.132 (4) 0.208 (5)
0.0293 (8) 0.0260 (8) 0.0333 (9) 0.0254 (8) 0.094 (3) 0.095 (3) 0.221 (7) 0.056 (2) 0.121 (3)
0.0251 (8) 0.0286 (8) 0.0325 (8) 0.0308 (8) 0.060 (2) 0.078 (2) 0.162 (5) 0.0294 (15) 0.104 (3)
−0.0033 (7) 0.0004 (6) 0.0009 (7) 0.0036 (6) −0.073 (4) 0.0011 (19) 0.038 (4) 0.028 (2) 0.046 (3)
0.0006 (6) 0.0000 (6) 0.0018 (6) 0.0078 (6) 0.040 (3) 0.0303 (18) 0.043 (3) 0.0154 (18) −0.036 (3)
0.0078 (6) 0.0032 (6) −0.0007 (7) −0.0080 (7) 0.004 (2) 0.044 (2) 0.146 (5) 0.0140 (14) 0.006 (2)
Geometric parameters (Å, º) Cl1—Mn1 K1—O6 K1—O9 K1—O10 K1—O5 K1—O7 K1—O8 K1—N9 K1—N10 Mn1—N3 Mn1—N2 Mn1—N1 Mn1—N4 C101—N1 C101—C301 C101—C201 C102—N1 C102—C302 C102—C202 C103—N2 C103—C302 C103—C203 C104—N2 C104—C303 C104—C204 C105—N3 C105—C303 C105—C205 C106—N3 C106—C304 C106—C206 C107—N4 C107—C304 C107—C207 C108—N4 C108—C301
Acta Cryst. (2015). C71, 545-548
2.3704 (6) 2.7851 (15) 2.8068 (16) 2.8271 (15) 2.8463 (15) 2.8478 (15) 2.8950 (15) 2.9862 (19) 3.0039 (18) 2.1452 (16) 2.1529 (15) 2.1538 (16) 2.1550 (16) 1.369 (2) 1.406 (3) 1.445 (3) 1.364 (2) 1.405 (3) 1.444 (3) 1.366 (2) 1.407 (3) 1.444 (3) 1.370 (2) 1.404 (3) 1.450 (3) 1.369 (2) 1.408 (3) 1.445 (3) 1.369 (2) 1.407 (3) 1.449 (3) 1.366 (2) 1.403 (3) 1.448 (3) 1.369 (2) 1.406 (3)
C30—C32 C30—C33 C30—C31 C31—H31A C31—H31B C31—H31C C32—H32A C32—H32B C32—H32C C33—H33A C33—H33B C33—H33C C34—C35 C34—C39 C35—C36 C35—H35A C36—C37 C36—H36A C37—C38 C37—H37A C38—C39 C38—H38A C39—N8 C40—O4 C40—N8 C40—C41 C41—C44 C41—C42 C41—C43 C42—H42A C42—H42B C42—H42C C43—H43A C43—H43B C43—H43C C44—H44A
1.527 (3) 1.531 (3) 1.533 (3) 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 1.387 (3) 1.406 (3) 1.386 (3) 0.9500 1.378 (3) 0.9500 1.384 (3) 0.9500 1.395 (3) 0.9500 1.409 (3) 1.218 (3) 1.362 (3) 1.534 (3) 1.523 (3) 1.530 (3) 1.534 (4) 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800
sup-9
supporting information C108—C208 C201—C202 C201—H20A C202—H20B C203—C204 C203—H20C C204—H20D C205—C206 C205—H20E C206—H20F C207—C208 C207—H20G C208—H20H C301—C1 C302—C12 C303—C23 C304—C34 C1—C2 C1—C6 C2—C3 C2—H2A C3—C4 C3—H3A C4—C5 C4—H4A C5—C6 C5—H5A C6—N5 C7—O1 C7—N5 C7—C8 C8—C11 C8—C9 C8—C10 C9—H9A C9—H9B C9—H9C C10—H10A C10—H10B C10—H10C C11—H11A C11—H11B C11—H11C C12—C13 C12—C17 C13—C14 C13—H13A C14—C15
Acta Cryst. (2015). C71, 545-548
1.443 (3) 1.345 (3) 0.9500 0.9500 1.349 (3) 0.9500 0.9500 1.350 (3) 0.9500 0.9500 1.348 (3) 0.9500 0.9500 1.501 (3) 1.496 (3) 1.500 (3) 1.500 (3) 1.387 (3) 1.405 (3) 1.384 (3) 0.9500 1.381 (3) 0.9500 1.383 (3) 0.9500 1.399 (3) 0.9500 1.408 (3) 1.213 (2) 1.354 (3) 1.537 (3) 1.526 (3) 1.526 (3) 1.533 (3) 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 1.390 (3) 1.397 (3) 1.385 (3) 0.9500 1.378 (3)
C44—H44B C44—H44C N5—H5 N6—H6A N7—H7A N8—H8A C45—N9 C45—C46 C45—H45A C45—H45B C46—O5 C46—H46A C46—H46B C47—O5 C47—C48 C47—H47A C47—H47B C48—O6 C48—H48A C48—H48B C49—O6 C49—C50 C49—H49A C49—H49B C50—N10 C50—H50A C50—H50B C51—N9 C51—C52 C51—H51A C51—H51B C52—O7 C52—H52A C52—H52B C53—O7 C53—C54 C53—H53A C53—H53B C54—O8 C54—H54A C54—H54B C55—O8 C55—C56 C55—H55A C55—H55B C56—N10 C56—H56A C56—H56B
0.9800 0.9800 0.8800 0.8800 0.8800 0.8800 1.467 (3) 1.499 (4) 0.9900 0.9900 1.430 (3) 0.9900 0.9900 1.418 (3) 1.496 (3) 0.9900 0.9900 1.421 (3) 0.9900 0.9900 1.420 (3) 1.509 (3) 0.9900 0.9900 1.468 (3) 0.9900 0.9900 1.465 (3) 1.504 (3) 0.9900 0.9900 1.424 (3) 0.9900 0.9900 1.423 (3) 1.495 (3) 0.9900 0.9900 1.417 (3) 0.9900 0.9900 1.423 (3) 1.504 (3) 0.9900 0.9900 1.465 (3) 0.9900 0.9900
sup-10
supporting information C14—H14A C15—C16 C15—H15A C16—C17 C16—H16A C17—N6 C18—O2 C18—N6 C18—C19 C19—C20 C19—C22 C19—C21 C20—H20I C20—H20J C20—H20K C21—H21A C21—H21B C21—H21C C22—H22A C22—H22B C22—H22C C23—C24 C23—C28 C24—C25 C24—H24A C25—C26 C25—H25A C26—C27 C26—H26A C27—C28 C27—H27A C28—N7 C29—O3 C29—N7 C29—C30
0.9500 1.383 (3) 0.9500 1.392 (3) 0.9500 1.404 (3) 1.213 (3) 1.368 (3) 1.534 (3) 1.526 (3) 1.530 (3) 1.534 (3) 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 0.9800 1.394 (3) 1.400 (3) 1.387 (3) 0.9500 1.386 (3) 0.9500 1.379 (3) 0.9500 1.390 (3) 0.9500 1.412 (3) 1.217 (3) 1.366 (3) 1.533 (3)
C57—N9 C57—C58 C57—H57A C57—H57B C58—O9 C58—H58A C58—H58B C59—O9 C59—C60 C59—H59A C59—H59B C60—O10 C60—H60A C60—H60B C61—O10 C61—C62 C61—H61A C61—H61B C62—N10 C62—H62A C62—H62B C1S—C2S C1S—O1S C1S—H1SA C1S—H1SB C2S—C3S C2S—H2SA C2S—H2SB C3S—C4S C3S—H3SA C3S—H3SB C4S—O1S C4S—H4SA C4S—H4SB
1.468 (3) 1.501 (4) 0.9900 0.9900 1.415 (3) 0.9900 0.9900 1.421 (3) 1.484 (3) 0.9900 0.9900 1.425 (3) 0.9900 0.9900 1.421 (3) 1.504 (3) 0.9900 0.9900 1.471 (3) 0.9900 0.9900 1.397 (6) 1.532 (6) 0.9900 0.9900 1.431 (5) 0.9900 0.9900 1.365 (6) 0.9900 0.9900 1.515 (4) 0.9900 0.9900
O6—K1—O9 O6—K1—O10 O9—K1—O10 O6—K1—O5 O9—K1—O5 O10—K1—O5 O6—K1—O7 O9—K1—O7 O10—K1—O7 O5—K1—O7 O6—K1—O8 O9—K1—O8
128.21 (5) 92.10 (5) 59.68 (5) 59.56 (5) 92.09 (5) 115.02 (5) 121.37 (5) 103.64 (5) 142.25 (5) 98.09 (5) 98.72 (4) 127.48 (5)
C30—C32—H32A C30—C32—H32B H32A—C32—H32B C30—C32—H32C H32A—C32—H32C H32B—C32—H32C C30—C33—H33A C30—C33—H33B H33A—C33—H33B C30—C33—H33C H33A—C33—H33C H33B—C33—H33C
109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5
Acta Cryst. (2015). C71, 545-548
sup-11
supporting information O10—K1—O8 O5—K1—O8 O7—K1—O8 O6—K1—N9 O9—K1—N9 O10—K1—N9 O5—K1—N9 O7—K1—N9 O8—K1—N9 O6—K1—N10 O9—K1—N10 O10—K1—N10 O5—K1—N10 O7—K1—N10 O8—K1—N10 N9—K1—N10 N3—Mn1—N2 N3—Mn1—N1 N2—Mn1—N1 N3—Mn1—N4 N2—Mn1—N4 N1—Mn1—N4 N3—Mn1—Cl1 N2—Mn1—Cl1 N1—Mn1—Cl1 N4—Mn1—Cl1 N1—C101—C301 N1—C101—C201 C301—C101—C201 N1—C102—C302 N1—C102—C202 C302—C102—C202 N2—C103—C302 N2—C103—C203 C302—C103—C203 N2—C104—C303 N2—C104—C204 C303—C104—C204 N3—C105—C303 N3—C105—C205 C303—C105—C205 N3—C106—C304 N3—C106—C206 C304—C106—C206 N4—C107—C304 N4—C107—C207 C304—C107—C207 N4—C108—C301
Acta Cryst. (2015). C71, 545-548
102.11 (5) 136.39 (5) 59.13 (4) 119.46 (5) 60.27 (5) 119.45 (5) 60.37 (5) 61.36 (5) 119.76 (5) 60.97 (5) 120.19 (5) 61.12 (5) 120.16 (5) 117.76 (5) 59.36 (5) 179.11 (5) 84.88 (6) 145.77 (6) 85.58 (6) 85.92 (6) 146.39 (6) 84.10 (6) 103.37 (4) 104.04 (4) 110.84 (5) 109.53 (5) 125.28 (17) 109.59 (17) 125.13 (17) 125.76 (17) 109.71 (17) 124.52 (18) 125.18 (17) 109.51 (16) 125.30 (18) 125.26 (17) 109.27 (16) 125.36 (17) 125.06 (17) 109.55 (16) 125.36 (17) 125.42 (17) 109.56 (16) 125.01 (18) 125.45 (17) 109.44 (17) 125.09 (18) 125.32 (17)
C35—C34—C39 C35—C34—C304 C39—C34—C304 C36—C35—C34 C36—C35—H35A C34—C35—H35A C37—C36—C35 C37—C36—H36A C35—C36—H36A C36—C37—C38 C36—C37—H37A C38—C37—H37A C37—C38—C39 C37—C38—H38A C39—C38—H38A C38—C39—C34 C38—C39—N8 C34—C39—N8 O4—C40—N8 O4—C40—C41 N8—C40—C41 C44—C41—C42 C44—C41—C43 C42—C41—C43 C44—C41—C40 C42—C41—C40 C43—C41—C40 C41—C42—H42A C41—C42—H42B H42A—C42—H42B C41—C42—H42C H42A—C42—H42C H42B—C42—H42C C41—C43—H43A C41—C43—H43B H43A—C43—H43B C41—C43—H43C H43A—C43—H43C H43B—C43—H43C C41—C44—H44A C41—C44—H44B H44A—C44—H44B C41—C44—H44C H44A—C44—H44C H44B—C44—H44C C7—N5—C6 C7—N5—H5 C6—N5—H5
119.16 (18) 120.36 (17) 120.46 (17) 121.17 (19) 119.4 119.4 119.16 (19) 120.4 120.4 121.18 (19) 119.4 119.4 119.76 (19) 120.1 120.1 119.55 (19) 123.53 (19) 116.90 (18) 122.7 (2) 122.98 (19) 114.31 (18) 108.9 (2) 110.2 (2) 109.5 (2) 108.34 (19) 109.91 (19) 110.0 (2) 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 129.58 (18) 115.2 115.2
sup-12
supporting information N4—C108—C208 C301—C108—C208 C202—C201—C101 C202—C201—H20A C101—C201—H20A C201—C202—C102 C201—C202—H20B C102—C202—H20B C204—C203—C103 C204—C203—H20C C103—C203—H20C C203—C204—C104 C203—C204—H20D C104—C204—H20D C206—C205—C105 C206—C205—H20E C105—C205—H20E C205—C206—C106 C205—C206—H20F C106—C206—H20F C208—C207—C107 C208—C207—H20G C107—C207—H20G C207—C208—C108 C207—C208—H20H C108—C208—H20H C108—C301—C101 C108—C301—C1 C101—C301—C1 C102—C302—C103 C102—C302—C12 C103—C302—C12 C104—C303—C105 C104—C303—C23 C105—C303—C23 C107—C304—C106 C107—C304—C34 C106—C304—C34 C102—N1—C101 C102—N1—Mn1 C101—N1—Mn1 C103—N2—C104 C103—N2—Mn1 C104—N2—Mn1 C106—N3—C105 C106—N3—Mn1 C105—N3—Mn1 C107—N4—C108
Acta Cryst. (2015). C71, 545-548
109.51 (17) 125.18 (17) 106.96 (18) 126.5 126.5 107.10 (18) 126.5 126.5 107.25 (17) 126.4 126.4 106.94 (17) 126.5 126.5 107.20 (17) 126.4 126.4 106.89 (18) 126.6 126.6 107.04 (18) 126.5 126.5 107.11 (17) 126.4 126.4 125.56 (17) 118.54 (17) 115.90 (17) 126.51 (18) 114.88 (17) 118.60 (17) 126.15 (17) 117.32 (16) 116.34 (16) 126.70 (18) 117.32 (17) 115.99 (17) 106.61 (16) 124.53 (13) 125.62 (13) 107.01 (15) 125.51 (12) 125.56 (12) 106.81 (16) 125.36 (12) 126.35 (13) 106.89 (16)
C18—N6—C17 C18—N6—H6A C17—N6—H6A C29—N7—C28 C29—N7—H7A C28—N7—H7A C40—N8—C39 C40—N8—H8A C39—N8—H8A N9—C45—C46 N9—C45—H45A C46—C45—H45A N9—C45—H45B C46—C45—H45B H45A—C45—H45B O5—C46—C45 O5—C46—H46A C45—C46—H46A O5—C46—H46B C45—C46—H46B H46A—C46—H46B O5—C47—C48 O5—C47—H47A C48—C47—H47A O5—C47—H47B C48—C47—H47B H47A—C47—H47B O6—C48—C47 O6—C48—H48A C47—C48—H48A O6—C48—H48B C47—C48—H48B H48A—C48—H48B O6—C49—C50 O6—C49—H49A C50—C49—H49A O6—C49—H49B C50—C49—H49B H49A—C49—H49B N10—C50—C49 N10—C50—H50A C49—C50—H50A N10—C50—H50B C49—C50—H50B H50A—C50—H50B N9—C51—C52 N9—C51—H51A C52—C51—H51A
129.93 (18) 115.0 115.0 126.88 (17) 116.6 116.6 130.20 (18) 114.9 114.9 113.8 (2) 108.8 108.8 108.8 108.8 107.7 108.99 (19) 109.9 109.9 109.9 109.9 108.3 109.51 (18) 109.8 109.8 109.8 109.8 108.2 108.91 (18) 109.9 109.9 109.9 109.9 108.3 108.85 (18) 109.9 109.9 109.9 109.9 108.3 114.01 (18) 108.8 108.8 108.8 108.8 107.6 114.3 (2) 108.7 108.7
sup-13
supporting information C107—N4—Mn1 C108—N4—Mn1 C2—C1—C6 C2—C1—C301 C6—C1—C301 C3—C2—C1 C3—C2—H2A C1—C2—H2A C4—C3—C2 C4—C3—H3A C2—C3—H3A C3—C4—C5 C3—C4—H4A C5—C4—H4A C4—C5—C6 C4—C5—H5A C6—C5—H5A C5—C6—C1 C5—C6—N5 C1—C6—N5 O1—C7—N5 O1—C7—C8 N5—C7—C8 C11—C8—C9 C11—C8—C10 C9—C8—C10 C11—C8—C7 C9—C8—C7 C10—C8—C7 C8—C9—H9A C8—C9—H9B H9A—C9—H9B C8—C9—H9C H9A—C9—H9C H9B—C9—H9C C8—C10—H10A C8—C10—H10B H10A—C10—H10B C8—C10—H10C H10A—C10—H10C H10B—C10—H10C C8—C11—H11A C8—C11—H11B H11A—C11—H11B C8—C11—H11C H11A—C11—H11C H11B—C11—H11C C13—C12—C17
Acta Cryst. (2015). C71, 545-548
124.74 (13) 126.10 (13) 118.55 (18) 120.56 (18) 120.79 (18) 121.67 (19) 119.2 119.2 119.3 (2) 120.3 120.3 120.6 (2) 119.7 119.7 120.0 (2) 120.0 120.0 119.83 (19) 123.37 (19) 116.77 (18) 122.6 (2) 122.07 (19) 115.29 (18) 110.2 (2) 109.2 (2) 109.3 (2) 108.19 (19) 112.96 (18) 106.84 (18) 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 119.25 (19)
N9—C51—H51B C52—C51—H51B H51A—C51—H51B O7—C52—C51 O7—C52—H52A C51—C52—H52A O7—C52—H52B C51—C52—H52B H52A—C52—H52B O7—C53—C54 O7—C53—H53A C54—C53—H53A O7—C53—H53B C54—C53—H53B H53A—C53—H53B O8—C54—C53 O8—C54—H54A C53—C54—H54A O8—C54—H54B C53—C54—H54B H54A—C54—H54B O8—C55—C56 O8—C55—H55A C56—C55—H55A O8—C55—H55B C56—C55—H55B H55A—C55—H55B N10—C56—C55 N10—C56—H56A C55—C56—H56A N10—C56—H56B C55—C56—H56B H56A—C56—H56B N9—C57—C58 N9—C57—H57A C58—C57—H57A N9—C57—H57B C58—C57—H57B H57A—C57—H57B O9—C58—C57 O9—C58—H58A C57—C58—H58A O9—C58—H58B C57—C58—H58B H58A—C58—H58B O9—C59—C60 O9—C59—H59A C60—C59—H59A
108.7 108.7 107.6 109.41 (19) 109.8 109.8 109.8 109.8 108.2 109.08 (18) 109.9 109.9 109.9 109.9 108.3 109.21 (19) 109.8 109.8 109.8 109.8 108.3 108.75 (18) 109.9 109.9 109.9 109.9 108.3 114.08 (17) 108.7 108.7 108.7 108.7 107.6 114.5 (2) 108.6 108.6 108.6 108.6 107.6 108.72 (19) 109.9 109.9 109.9 109.9 108.3 108.50 (19) 110.0 110.0
sup-14
supporting information C13—C12—C302 C17—C12—C302 C14—C13—C12 C14—C13—H13A C12—C13—H13A C15—C14—C13 C15—C14—H14A C13—C14—H14A C14—C15—C16 C14—C15—H15A C16—C15—H15A C15—C16—C17 C15—C16—H16A C17—C16—H16A C16—C17—C12 C16—C17—N6 C12—C17—N6 O2—C18—N6 O2—C18—C19 N6—C18—C19 C20—C19—C22 C20—C19—C18 C22—C19—C18 C20—C19—C21 C22—C19—C21 C18—C19—C21 C19—C20—H20I C19—C20—H20J H20I—C20—H20J C19—C20—H20K H20I—C20—H20K H20J—C20—H20K C19—C21—H21A C19—C21—H21B H21A—C21—H21B C19—C21—H21C H21A—C21—H21C H21B—C21—H21C C19—C22—H22A C19—C22—H22B H22A—C22—H22B C19—C22—H22C H22A—C22—H22C H22B—C22—H22C C24—C23—C28 C24—C23—C303 C28—C23—C303 C25—C24—C23
Acta Cryst. (2015). C71, 545-548
120.38 (18) 120.08 (18) 120.5 (2) 119.8 119.8 119.7 (2) 120.2 120.2 121.0 (2) 119.5 119.5 119.4 (2) 120.3 120.3 120.1 (2) 123.0 (2) 116.81 (18) 123.0 (2) 123.9 (2) 113.14 (18) 109.16 (19) 108.48 (18) 109.50 (18) 109.90 (19) 110.32 (19) 109.45 (19) 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 109.5 118.38 (17) 119.46 (17) 122.16 (17) 121.59 (19)
O9—C59—H59B C60—C59—H59B H59A—C59—H59B O10—C60—C59 O10—C60—H60A C59—C60—H60A O10—C60—H60B C59—C60—H60B H60A—C60—H60B O10—C61—C62 O10—C61—H61A C62—C61—H61A O10—C61—H61B C62—C61—H61B H61A—C61—H61B N10—C62—C61 N10—C62—H62A C61—C62—H62A N10—C62—H62B C61—C62—H62B H62A—C62—H62B C51—N9—C45 C51—N9—C57 C45—N9—C57 C51—N9—K1 C45—N9—K1 C57—N9—K1 C56—N10—C50 C56—N10—C62 C50—N10—C62 C56—N10—K1 C50—N10—K1 C62—N10—K1 C47—O5—C46 C47—O5—K1 C46—O5—K1 C49—O6—C48 C49—O6—K1 C48—O6—K1 C53—O7—C52 C53—O7—K1 C52—O7—K1 C54—O8—C55 C54—O8—K1 C55—O8—K1 C58—O9—C59 C58—O9—K1 C59—O9—K1
110.0 110.0 108.4 110.10 (18) 109.6 109.6 109.6 109.6 108.2 108.49 (18) 110.0 110.0 110.0 110.0 108.4 113.32 (18) 108.9 108.9 108.9 108.9 107.7 109.76 (19) 110.11 (19) 110.12 (19) 108.72 (13) 110.34 (13) 107.74 (13) 110.12 (17) 109.19 (17) 109.66 (17) 111.32 (12) 107.93 (12) 108.60 (12) 111.04 (17) 114.11 (13) 115.94 (12) 111.65 (17) 117.87 (12) 117.93 (13) 110.61 (17) 115.37 (13) 113.64 (13) 111.31 (16) 114.16 (12) 117.13 (12) 111.98 (17) 120.80 (13) 115.74 (13)
sup-15
supporting information C25—C24—H24A C23—C24—H24A C26—C25—C24 C26—C25—H25A C24—C25—H25A C27—C26—C25 C27—C26—H26A C25—C26—H26A C26—C27—C28 C26—C27—H27A C28—C27—H27A C27—C28—C23 C27—C28—N7 C23—C28—N7 O3—C29—N7 O3—C29—C30 N7—C29—C30 C32—C30—C33 C32—C30—C29 C33—C30—C29 C32—C30—C31 C33—C30—C31 C29—C30—C31 C30—C31—H31A C30—C31—H31B H31A—C31—H31B C30—C31—H31C H31A—C31—H31C H31B—C31—H31C
Acta Cryst. (2015). C71, 545-548
119.2 119.2 119.05 (19) 120.5 120.5 120.51 (18) 119.7 119.7 120.40 (19) 119.8 119.8 120.07 (18) 121.63 (18) 118.23 (17) 122.21 (19) 120.73 (19) 117.06 (17) 110.0 (2) 114.59 (18) 106.69 (17) 109.68 (19) 108.89 (19) 106.82 (18) 109.5 109.5 109.5 109.5 109.5 109.5
C61—O10—C60 C61—O10—K1 C60—O10—K1 C2S—C1S—O1S C2S—C1S—H1SA O1S—C1S—H1SA C2S—C1S—H1SB O1S—C1S—H1SB H1SA—C1S—H1SB C1S—C2S—C3S C1S—C2S—H2SA C3S—C2S—H2SA C1S—C2S—H2SB C3S—C2S—H2SB H2SA—C2S—H2SB C4S—C3S—C2S C4S—C3S—H3SA C2S—C3S—H3SA C4S—C3S—H3SB C2S—C3S—H3SB H3SA—C3S—H3SB C3S—C4S—O1S C3S—C4S—H4SA O1S—C4S—H4SA C3S—C4S—H4SB O1S—C4S—H4SB H4SA—C4S—H4SB C4S—O1S—C1S
110.92 (16) 111.37 (12) 115.33 (13) 108.0 (3) 110.1 110.1 110.1 110.1 108.4 106.8 (4) 110.4 110.4 110.4 110.4 108.6 112.5 (4) 109.1 109.1 109.1 109.1 107.8 106.5 (3) 110.4 110.4 110.4 110.4 108.6 101.4 (4)
sup-16
