metal-organic compounds Acta Crystallographica Section C

Received 27 August 2013 Accepted 2 October 2013

process providing the necessary charge balance to permit the construction of a wide range of coordination polymers (Perry et al., 2009). Dipyridyl ligands can also be added in the reaction systems to produce more complicated compounds, because these ligands can satisfy and even mediate the coordination requirements of the metal centres (Liu et al., 2010, 2011). Among the aforementioned ligands, flexible candidates can not only adopt various conformations but also show different coordination modes to bind metal atoms. Therefore, flexible ligands are more prone to forming complexes with unexpected structures (Sposato et al., 2010). We report herein the synthesis and structure of a cadmium coordination polymer, poly[aqua{2-1,4-bis[2-(pyridin-4-yl)ethenyl]benzene-2N:N0 }[42,20 -(1,4-phenylene)diacetato-4O,O0 :O00 ,O000 ]cadmium(II)], (I), which was constructed from the flexible ligands 1,4-bis[2(pyridin-4-yl)ethenyl]benzene (1,4-bpeb) and 2,20 -(1,4-phenylene)diacetic acid (1,4-H2pda) under hydrothermal conditions.

A novel three-dimensional CdII complex, poly[aqua{2-1,4bis[2-(pyridin-4-yl)ethenyl]benzene-2 N:N 0 }[4 -2,2 0 -(1,4phenylene)diacetato-4O,O0 :O00 ,O000 ]cadmium(II)], [Cd(C10H8O4)(C20H16N2)(H2O)]n, has been prepared by hydrothermal assembly of Cd(NO3)24H2O, 1,4-bis[2-(pyridin-4-yl)ethenyl]benzene (1,4-bpeb) and 2,20 -(1,4-phenylene)diacetic acid (1,4-H2pda). Each CdII centre is located on a twofold axis in a distorted pentagonal bipyramidal coordination environment formed by one O atom from a water molecule, which lies on the same twofold axis, four O atoms from two different 1,4pda ligands and two N atoms from two different 1,4-bpeb ligands. The CdII centres are bridged by the 1,4-bpeb and 1,4pda ligands, which lie across centres of inversion. The threedimensional net can be regarded as a diamondoid network by treating the CdII atoms as nodes and the 1,4-bpeb and 1,4-pda ligands as linkers. The single net leaves voids that are filled by mutual interpenetration of four independent equivalent frameworks in a fivefold interpenetrating architecture.

2. Experimental

Crystal Structure Communications ISSN 0108-2701

A fivefold interpenetrating diamondoid framework constructed by flexible dipyridyl and dicarboxylate ligands Jun-Feng Wang, Wen-Jing Guo and Fan-Zheng Deng* College of Chemistry and Materials Science, Huaibei Normal University, Huaibei 235000, Anhui, People’s Republic of China Correspondence e-mail: [email protected]

2.1. Synthesis and crystallization

Keywords: crystal structure; fivefold interpenetrating diamondoid framework; 2,20 -(1,4-phenylene)diacetic acid; metal–organic coordination polymers; 1,4-bis[2-(pyridin-4yl)ethenyl]benzene.

1. Introduction In recent years, metal–organic coordination polymers have been widely studied as they represent an important interface between synthetic chemistry and materials science, and they have fascinating topological structures, unique properties and reactivities that are not found in discrete coordination compounds (Abrahams et al., 1999; Kreno et al., 2012; Yoon et al., 2012). It is well known that the proper choice of metal ions and organic ligands is a key point in the design and synthesis of high-dimensional functional coordination polymers (Perry et al., 2009). Considering the various compounds reported to date, we noted that dianionic dicarboxylate ligands have been widely employed to conjoin cationic metal centres, in the

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A mixture of Cd(NO3)24H2O (31 mg, 0.1 mmol), 1,4-H2pda (19 mg, 0.1 mmol), 1,4-bpeb (28 mg, 0.1 mmol) and distilled water (10 ml) was added to a 25 ml Teflon-lined stainless steel autoclave. The autoclave was sealed and heated in an oven to 443 K for 2 d, and then cooled to ambient temperature at a rate of 5 K h1 to form yellow crystals of (I), which were washed with water–ethanol (1:1 v/v) and dried in air (yield 49 mg, 81%, based on Cd). Analysis calculated for C30H26CdN2O5: C 59.37, H 4.32, N 4.62%; found: C 59.76, H 4.03, N 4.91%. IR (KBr, , cm1): 3442 (m), 3031 (m), 1615 (s), 1558 (s), 1433 (m), 1384 (s), 1225 (w), 1203 (m), 1085 (m), 1026 (m), 957 (m), 834 (s), 756 (s), 718 (s), 619 (m), 554 (s), 435 (m). 2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. The unique H atom of the coordinated water molecule was located from a Fourier map

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metal-organic compounds Table 1 Experimental details. Crystal data Chemical formula Mr Crystal system, space group Temperature (K) ˚) a, b, c (A ( ) ˚ 3) V (A Z Radiation type  (mm1) Crystal size (mm) Data collection Diffractometer Absorption correction Tmin, Tmax No. of measured, independent and observed [I > 2(I)] reflections Rint ˚ 1) (sin /)max (A Refinement R[F 2 > 2(F 2)], wR(F 2), S No. of reflections No. of parameters H-atom treatment ˚ 3)
max,
min (e A

[Cd(C10H8O4)(C20H16N2)(H2O)] 606.94 Monoclinic, C2/c 223 18.537 (4), 16.886 (3), 8.3534 (17) 101.26 (3) 2564.4 (9) 4 Mo K 0.90 0.20  0.17  0.15

Bruker SMART CCD area-detector diffractometer Multi-scan (SADABS; Bruker, 1997) 0.841, 0.877 11458, 2937, 2641 0.033 0.649

0.032, 0.077, 1.14 2937 174 H-atom parameters constrained 1.19, 0.64

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

and included in the final refinement with the O—H distance ˚ and with Uiso(H) = 1.5Ueq(O). All other constrained to 0.85 A H atoms were placed in geometrically idealized positions, with ˚ for phenyl, pyridine and vinyl groups, and C—H = 0.94 A ˚ C—H = 0.98 A for the methylene group, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

3. Results and discussion As shown in Fig. 1, each CdII centre of the title compound, (I), has a {CdN2O5} coordination environment consisting of two N

Figure 2 A view of the one-dimensional [Cd(1,4-pda)]n chain in (I).

atoms from two 1,4-bpeb ligands, four O atoms from two 1,4pda ligands and one O atom from a water molecule. The coordination number and environment of the CdII centre are similar to those in {[Cd(suc)(bpfp)(H2O)]2H2O}n, (II) [suc is succinate and bpfp is bis(pyridin-4-ylformyl)piperazine; Pochodylo & LaDuca (2012)]. The coordination geometry is not a typical pentagonal bipyramid, in that the O3—Cd1—N1 and N1—Cd1—N1i angles [symmetry code: (i) x, y, z  12] are 84.15 (5) and 168.29 (9) , respectively, very different from a regular pentagonal bipyramidal angle. Thus, the geometry can be described as highly distorted pentagonal bipyramidal. The Cd—O and Cd—N bond lengths are similar to those found in (II). Each CdII cation is linked to a terminal aqua ligand to form a [Cd(H2O)]2+ unit, which sits on a twofold axis. These [Cd(OH2)]2+ units are interlinked by centrosymmetric bis-bidentate 1,4-pda ligands to afford a one-dimensional [Cd(1,4-pda)(H2O)]n chain (Fig. 2). The 1,4-bpeb ligands also act as centrosymmetric bridges to connect adjacent [Cd(1,4pda)(H2O)]n chains, giving rise to a three-dimensional [Cd(1,4-pda)(1,4-bpeb)(H2O)]n framework (Fig. 3). Topologically, each CdII cation acts as a strongly distorted tetrahedral node to form a single adamantane-type unit (Fig. 4). In each such adamantane-type unit, the Cd  Cd distance bridged by di˚ , while that separated by carboxylate groups is 11.636 (3) A ˚ 1,4-bpeb ligands is 20.704 (4) A. The void of such a net is big enough to allow the four other nets to penetrate, forming a fivefold interpenetrating 66-diamondoid framework (Fig. 5).

Figure 1 The coordination environment of the CdII cation in (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (i) x, y, z  12; (ii) x + 1, y + 1, z + 1; (iii) x  12, y + 12, z; (iv) x  1, y + 1, z  32; (v) x + 12, y + 12, z  12.] Acta Cryst. (2013). C69, 1328–1331

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Figure 3 A view of the three-dimensional network of (I).

Diamondoid networks have previously been identified in both ZnII and CdII compounds in which the metal centres are bridged by carboxylate and pyridine-based ligands (Blatov et al., 2004; Li et al., 2004; Zhou et al., 2012). In these structures, it is common for each of the metal centres to be coordinated by two pyridyl groups and two carboxylate groups, thus allowing each metal centre to serve as a 4-connecting node. In (I), a water molecule completes the coordination environment of the seven-coordinate metal centre, but it serves only as an appendage to the network and does not affect the topological description of the coordination polymer as a diamondoid network. There are numerous examples in the literature of interpenetration occurring with diamondoid networks, with the most common mode of interpenetration involving translation of equally spaced networks along a twofold axis (Batten & Robson, 1998; Blatov et al., 2004). In the structure of (I), there are five interpenetrating networks but the mode of interpenetration is very different to that commonly found, with the five nets not related by a translation along a twofold axis or

even a pseudo-twofold axis. Ermer (1988) also reported an unusual mode of fivefold interpenetration of diamondoid networks. Discussions of nonregular modes of interpenetration of diamondoid networks have been presented in the literature (Batten & Robson, 1998; Blatov et al., 2004). The flexibility of the organic ligands is also important for the formation of (I), because they can rotate freely to satisfy the coordination requirements of the metal centres as well as the packing modes of the whole structure. In contrast with the rigid dicarboxylate, the flexible 1,4-pda ligand allows adjustment of the angles between adjacent CdII centres, which determines the structure of (I). In summary, we have demonstrated the construction of a unique fivefold diamondoid framework, (I), from the hydrothermal reaction of Cd(NO3)24H2O with 1,4-bpeb and 1,4-

Figure 4

Figure 5

A view of an adamantane-type unit within the network of (I).

The fivefold interpenetrating diamondoid network in (I).

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metal-organic compounds H2pda. The results indicate that the terminal aqua ligands and flexible organic ligands may have significant effects on the formation of the final structure. It is expected that in other systems containing water, flexible carboxylate and dipyridinyl ligands can produce other multidimensional interpenetrating coordination polymers with interesting structures. This work was supported by Huaibei Normal University. Supplementary data for this paper are available from the IUCr electronic archives (Reference: YP3048). Services for accessing these data are described at the back of the journal.

References Abrahams, B. F., Batten, S. R., Grannas, M. J., Hamit, H., Hoskins, B. F. & Robson, R. (1999). Angew. Chem. Int. Ed. 38, 1475–1477. Batten, S. R. & Robson, R. (1998). Angew. Chem. Int. Ed. 37, 1460–1494.

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Blatov, V. A., Carlucci, L., Ciani, G. & Proserpio, D. M. (2004). CrystEngComm, 6, 377–395. Bruker (1997). SMART and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA. Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Ermer, O. (1988). J. Am. Chem. Soc. 110, 3141–3754. Kreno, L. E., Leong, K., Farha, O. K., Allendorf, M., Van Duyne, R. P. & Hupp, J. T. (2012). Chem. Rev. 112, 1105–1125. Li, X.-J., Cao, R., Sun, D.-F., Bi, W.-H., Wang, Y.-Q., Li, X. & Hong, M.-C. (2004). Cryst. Growth Des. 4, 775–780. Liu, D., Chang, Y.-J. & Lang, J.-P. (2011). CrystEngComm, 13, 1851–1857. Liu, D., Ren, Z.-G., Li, H.-X., Lang, J.-P., Li, N.-Y. & Abrahams, B. F. (2010). Angew. Chem. Int. Ed. 49, 4767–4770. Perry, J. J. IV, Perman, J. A. & Zaworotko, M. J. (2009). Chem. Soc. Rev. 38, 1400–1417. Pochodylo, A. L. & LaDuca, R. L. (2012). Inorg. Chim. Acta, 389, 191–201. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Spek, A. L. (2009). Acta Cryst. D65, 148–155. Sposato, L. K., Nettleman, J. A. & LaDuca, R. L. (2010). CrystEngComm, 12, 2374–2380. Yoon, M., Srirambalaji, R. & Kim, K. (2012). Chem. Rev. 112, 1196–1231. Zhou, X., Li, B., Li, G., Zhou, Q., Shi, Z. & Feng, S. (2012). CrystEngComm, 14, 4664–4669.

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supplementary materials Acta Cryst. (2013). C69, 1328-1331

[doi:10.1107/S0108270113027182]

A fivefold interpenetrating diamondoid framework constructed by flexible dipyridyl and dicarboxylate ligands Jun-Feng Wang, Wen-Jing Guo and Fan-Zheng Deng Computing details Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009). Poly[aqua{µ2-1,4-bis[2-(pyridin-4-yl)ethenyl]benzene-κ2N:N′}[µ4-2,2′-(1,4-phenylene)diacetatoκ4O,O′:O′′,O′′′]cadmium(II)] Crystal data [Cd(C10H8O4)(C20H16N2)(H2O)] Mr = 606.94 Monoclinic, C2/c Hall symbol: -C 2yc a = 18.537 (4) Å b = 16.886 (3) Å c = 8.3534 (17) Å β = 101.26 (3)° V = 2564.4 (9) Å3 Z=4

F(000) = 1232 Dx = 1.572 Mg m−3 Mo Kα radiation, λ = 0.71073 Å Cell parameters from 6132 reflections θ = 3.0–27.5° µ = 0.90 mm−1 T = 223 K Block, yellow 0.20 × 0.17 × 0.15 mm

Data collection Bruker SMART CCD area-detector diffractometer Radiation source: fine-focus sealed tube Graphite monochromator φ and ω scans Absorption correction: multi-scan (SADABS; Bruker, 1997) Tmin = 0.841, Tmax = 0.877

11458 measured reflections 2937 independent reflections 2641 reflections with I > 2σ(I) Rint = 0.033 θmax = 27.5°, θmin = 3.2° h = −24→17 k = −20→21 l = −10→9

Refinement Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.032 wR(F2) = 0.077 S = 1.14 2937 reflections 174 parameters 0 restraints Acta Cryst. (2013). C69, 1328-1331

Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained

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supplementary materials w = 1/[σ2(Fo2) + (0.0429P)2] where P = (Fo2 + 2Fc2)/3 (Δ/σ)max < 0.001 Δρmax = 1.19 e Å−3

Δρmin = −0.64 e Å−3 Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction coefficient: 0.0073 (4)

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)

Cd1 N1 O1 O2 O3 H1W C1 H1 C2 H2 C3 C4 H4 C5 H5 C6 H6 C7 H7 C8 C9 H9 C10 H10 C11 H11 C12 C13 H13 C14 H14A H14B C15

x

y

z

Uiso*/Ueq

0.0000 0.12006 (11) −0.04623 (11) −0.04436 (11) 0.0000 −0.0151 0.17741 (14) 0.1698 0.24752 (14) 0.2861 0.26146 (13) 0.20107 (14) 0.2071 0.13303 (14) 0.0935 0.33442 (14) 0.3665 0.35898 (14) 0.3269 0.43147 (13) 0.45649 (14) 0.4267 0.47621 (14) 0.4604 −0.20096 (14) −0.1679 −0.17611 (13) −0.22592 (15) −0.2099 −0.09549 (14) −0.0707 −0.0917 −0.05847 (12)

0.371789 (12) 0.38606 (11) 0.26880 (10) 0.38739 (10) 0.51095 (14) 0.5424 0.34306 (15) 0.3046 0.35233 (15) 0.3205 0.40866 (14) 0.45446 (14) 0.4942 0.44152 (14) 0.4730 0.41656 (15) 0.3731 0.48043 (15) 0.5240 0.48958 (14) 0.56443 (14) 0.6087 0.42438 (14) 0.3729 0.18840 (15) 0.1459 0.26537 (15) 0.32652 (15) 0.3791 0.28267 (17) 0.2340 0.3215 0.31506 (14)

−0.2500 −0.0941 (2) −0.1026 (2) 0.0024 (2) −0.2500 −0.3289 −0.1179 (3) −0.2010 −0.0264 (3) −0.0482 0.0984 (3) 0.1198 (3) 0.2002 0.0238 (3) 0.0413 0.2006 (3) 0.2057 0.2871 (3) 0.2788 0.3944 (3) 0.4483 (3) 0.4141 0.4496 (3) 0.4170 0.0389 (3) 0.0644 0.0695 (3) 0.0292 (3) 0.0483 0.1395 (3) 0.1845 0.2279 0.0051 (3)

0.02882 (11) 0.0344 (4) 0.0438 (4) 0.0413 (4) 0.0431 (6) 0.065* 0.0383 (5) 0.046* 0.0388 (5) 0.047* 0.0348 (5) 0.0395 (6) 0.047* 0.0378 (5) 0.045* 0.0384 (5) 0.046* 0.0380 (5) 0.046* 0.0342 (5) 0.0371 (5) 0.045* 0.0374 (5) 0.045* 0.0409 (6) 0.049* 0.0359 (5) 0.0426 (6) 0.051* 0.0430 (6) 0.052* 0.052* 0.0325 (5)

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supplementary materials Atomic displacement parameters (Å2)

Cd1 N1 O1 O2 O3 C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 C14 C15

U11

U22

U33

U12

U13

U23

0.02084 (15) 0.0245 (11) 0.0516 (12) 0.0469 (11) 0.0539 (17) 0.0313 (14) 0.0260 (13) 0.0251 (12) 0.0320 (14) 0.0279 (13) 0.0240 (13) 0.0288 (13) 0.0259 (13) 0.0300 (13) 0.0307 (14) 0.0355 (14) 0.0298 (13) 0.0410 (15) 0.0332 (14) 0.0193 (11)

0.02927 (16) 0.0354 (10) 0.0328 (9) 0.0355 (9) 0.0311 (12) 0.0361 (12) 0.0395 (13) 0.0355 (12) 0.0390 (13) 0.0381 (13) 0.0440 (14) 0.0390 (13) 0.0377 (13) 0.0329 (12) 0.0330 (12) 0.0407 (13) 0.0481 (14) 0.0361 (13) 0.0570 (16) 0.0391 (13)

0.03468 (16) 0.0402 (10) 0.0510 (10) 0.0410 (9) 0.0397 (12) 0.0438 (13) 0.0486 (14) 0.0408 (12) 0.0443 (13) 0.0449 (13) 0.0447 (13) 0.0444 (13) 0.0374 (11) 0.0456 (13) 0.0460 (13) 0.0465 (13) 0.0303 (11) 0.0507 (14) 0.0380 (13) 0.0364 (12)

0.000 0.0001 (8) −0.0015 (8) −0.0082 (8) 0.000 0.0012 (10) 0.0043 (10) −0.0042 (10) 0.0005 (10) 0.0040 (10) −0.0002 (10) −0.0013 (10) −0.0027 (10) 0.0015 (10) −0.0049 (10) 0.0005 (11) −0.0074 (10) −0.0090 (11) −0.0088 (12) −0.0022 (9)

0.00127 (9) −0.0010 (8) 0.0198 (8) 0.0069 (8) −0.0025 (11) −0.0020 (10) 0.0014 (10) −0.0013 (9) 0.0000 (10) 0.0012 (10) 0.0011 (10) 0.0028 (10) 0.0024 (9) 0.0006 (10) 0.0012 (10) 0.0082 (11) 0.0075 (9) 0.0091 (11) 0.0046 (10) −0.0013 (9)

0.000 0.0020 (8) 0.0004 (7) −0.0027 (7) 0.000 −0.0029 (10) −0.0018 (10) 0.0030 (9) −0.0059 (10) −0.0012 (10) −0.0016 (10) 0.0013 (10) −0.0012 (9) 0.0006 (9) −0.0033 (9) 0.0047 (10) 0.0014 (9) −0.0013 (10) 0.0055 (11) 0.0029 (9)

Geometric parameters (Å, º) Cd1—O3 Cd1—N1i Cd1—N1 Cd1—O1 Cd1—O1i Cd1—O2i Cd1—O2 Cd1—C15 Cd1—C15i N1—C1 N1—C5 O1—C15 O2—C15 O3—H1W C1—C2 C1—H1 C2—C3 C2—H2 C3—C4 C3—C6 C4—C5 C4—H4

2.350 (2) 2.361 (2) 2.361 (2) 2.3845 (17) 2.3845 (17) 2.4221 (18) 2.4221 (18) 2.745 (2) 2.745 (2) 1.334 (3) 1.346 (3) 1.246 (3) 1.250 (3) 0.8499 1.382 (3) 0.9400 1.397 (3) 0.9400 1.401 (3) 1.458 (3) 1.374 (3) 0.9400

C5—H5 C6—C7 C6—H6 C7—C8 C7—H7 C8—C9 C8—C10 C9—C10ii C9—H9 C10—C9ii C10—H10 C11—C12 C11—C13iii C11—H11 C12—C13 C12—C14 C13—C11iii C13—H13 C14—C15 C14—H14A C14—H14B

0.9400 1.328 (3) 0.9400 1.471 (3) 0.9400 1.390 (3) 1.401 (3) 1.380 (3) 0.9400 1.380 (3) 0.9400 1.386 (3) 1.387 (4) 0.9400 1.382 (4) 1.523 (3) 1.387 (4) 0.9400 1.526 (3) 0.9800 0.9800

O3—Cd1—N1i

84.15 (5)

C3—C2—H2

119.8

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supplementary materials O3—Cd1—N1 N1i—Cd1—N1 O3—Cd1—O1 N1i—Cd1—O1 N1—Cd1—O1 O3—Cd1—O1i N1i—Cd1—O1i N1—Cd1—O1i O1—Cd1—O1i O3—Cd1—O2i N1i—Cd1—O2i N1—Cd1—O2i O1—Cd1—O2i O1i—Cd1—O2i O3—Cd1—O2 N1i—Cd1—O2 N1—Cd1—O2 O1—Cd1—O2 O1i—Cd1—O2 O2i—Cd1—O2 O3—Cd1—C15 N1i—Cd1—C15 N1—Cd1—C15 O1—Cd1—C15 O1i—Cd1—C15 O2i—Cd1—C15 O2—Cd1—C15 O3—Cd1—C15i N1i—Cd1—C15i N1—Cd1—C15i O1—Cd1—C15i O1i—Cd1—C15i O2i—Cd1—C15i O2—Cd1—C15i C15—Cd1—C15i C1—N1—C5 C1—N1—Cd1 C5—N1—Cd1 C15—O1—Cd1 C15—O2—Cd1 Cd1—O3—H1W N1—C1—C2 N1—C1—H1 C2—C1—H1 C1—C2—C3 C1—C2—H2

84.14 (5) 168.29 (9) 136.83 (4) 87.94 (7) 100.65 (7) 136.83 (4) 100.64 (7) 87.94 (7) 86.35 (8) 83.75 (4) 87.28 (7) 91.45 (7) 138.24 (6) 54.03 (6) 83.76 (4) 91.45 (7) 87.28 (7) 54.03 (6) 138.24 (6) 167.51 (8) 110.42 (5) 89.50 (7) 94.59 (7) 26.95 (6) 112.49 (7) 165.07 (7) 27.09 (6) 110.42 (5) 94.59 (7) 89.50 (7) 112.49 (7) 26.95 (6) 27.09 (6) 165.07 (7) 139.16 (10) 117.0 (2) 123.71 (16) 119.27 (16) 92.89 (14) 91.02 (13) 128.6 123.1 (2) 118.4 118.4 120.4 (2) 119.8

C2—C3—C4 C2—C3—C6 C4—C3—C6 C5—C4—C3 C5—C4—H4 C3—C4—H4 N1—C5—C4 N1—C5—H5 C4—C5—H5 C7—C6—C3 C7—C6—H6 C3—C6—H6 C6—C7—C8 C6—C7—H7 C8—C7—H7 C9—C8—C10 C9—C8—C7 C10—C8—C7 C10ii—C9—C8 C10ii—C9—H9 C8—C9—H9 C9ii—C10—C8 C9ii—C10—H10 C8—C10—H10 C12—C11—C13iii C12—C11—H11 C13iii—C11—H11 C13—C12—C11 C13—C12—C14 C11—C12—C14 C12—C13—C11iii C12—C13—H13 C11iii—C13—H13 C12—C14—C15 C12—C14—H14A C15—C14—H14A C12—C14—H14B C15—C14—H14B H14A—C14—H14B O1—C15—O2 O1—C15—C14 O2—C15—C14 O1—C15—Cd1 O2—C15—Cd1 C14—C15—Cd1

115.8 (2) 121.0 (2) 123.2 (2) 120.2 (2) 119.9 119.9 123.4 (2) 118.3 118.3 125.0 (2) 117.5 117.5 126.3 (2) 116.8 116.8 118.0 (2) 120.0 (2) 122.0 (2) 121.9 (2) 119.0 119.0 120.1 (2) 120.0 120.0 120.6 (2) 119.7 119.7 118.3 (2) 120.6 (2) 121.1 (2) 121.1 (2) 119.4 119.4 109.57 (19) 109.8 109.8 109.8 109.8 108.2 122.1 (2) 118.6 (2) 119.3 (2) 60.16 (12) 61.90 (12) 176.42 (16)

Symmetry codes: (i) −x, y, −z−1/2; (ii) −x+1, −y+1, −z+1; (iii) −x−1/2, −y+1/2, −z.

Acta Cryst. (2013). C69, 1328-1331

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