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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): m714.
Published online 2010 May 29. doi:  10.1107/S1600536810019148
PMCID: PMC2979405

Bis{1,2-bis­[2-(1H-imidazol-1-yl)eth­oxy]ethane-κ2 N 3,N 3′}dichloridocadmium(II) monohydrate

Abstract

The asymmetric unit of the title compound, [CdCl2(C12H18N4O2)2]·H2O, contains one water mol­ecule and two halves of a [CdCl2(BIEE)2] complex mol­ecule {BIEE is 1,2-bis­[2-(1H-imidazol-1-yl)eth­oxy]ethane}, with the CdII atoms lying on inversion centres. Each metal atom displays an elongated octa­hedral coordination geometry provided by two trans-arranged chloride anions and four N atoms from two BIEE ligands. Weak O—H(...)Cl hydrogen-bond inter­actions contribute to the stability of the crystal packing.

Related literature

For general background to flexible bis­(imidazole) ligands, see: Liu et al. (2007 [triangle]); Wen et al. (2007 [triangle]); Jin et al. (2006 [triangle]). For a related structure, see: Liu et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m714-scheme1.jpg

Experimental

Crystal data

  • [CdCl2(C12H18N4O2)2]·H2O
  • M r = 701.92
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m714-efi1.jpg
  • a = 15.3629 (13) Å
  • b = 11.0659 (9) Å
  • c = 18.4492 (16) Å
  • β = 102.558 (1)°
  • V = 3061.4 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.94 mm−1
  • T = 293 K
  • 0.26 × 0.22 × 0.20 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.793, T max = 0.835
  • 21862 measured reflections
  • 5691 independent reflections
  • 4148 reflections with I > 2σ(I)
  • R int = 0.022

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.087
  • S = 1.04
  • 5691 reflections
  • 372 parameters
  • 8 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.53 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810019148/rz2451sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810019148/rz2451Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20971004), the Key Project of the Chinese Ministry of Education (No. 210102) and the Natural Science Foundation of the Educational Commission of Anhui Province of China (No. KJ2010A229).

supplementary crystallographic information

Comment

A large number of beautiful metal organic frameworks (MOFs) of ingenious design based on flexible bis(imidazole) ligands, such as (N-im)2(CH2)n (n = 1-4), have recently been constructed (Liu et al., 2007; Wen et al., 2007; Jin et al., 2006). These ligands bearing alkyl spacers are good choices of N-donor ligands, because the flexible nature of the spacers allows the ligands to bend and rotate when it coordinates to metal centers. The structures and properties also can be modified by changing the spacer groups, for an instance, by varying the length of the spacer. We designed and prepared a long ligand, 1,2-bis(2-(1H-imidazol-1-yl)ethoxy)ethane (BIEE), which is longer than 1,1'-(2,2'-oxybis(ethane-2,1-diyl))bis(1H-imidazole)) (obbm). The increasing length may control the physical dimensions of the crystalline architecture and, accordingly, affects the internal chemistry of the coordination polymers. Therefore, the exploration of this ligand is necessary in order to enrich and develop this field.

The molecular structure of the title compound is shown in Fig. 1. The asymmetric unit contains one water molecule and two crystallographically independent half of a [CdCl2(BIEE)2] complex molecule, with the metal atoms lying on inversion centres. Each cadmium(II) atom displays an elongated octahedral coordination geometry, with four N atoms from two BIEE ligands providing the equatorial plane and two Cl anions at the axial positions. The Cd—N lengths range from 2.328 (2) to 2.365 (2) Å; these values agree well with those observed in [Cd(NCS)2(1-vinylimidazole)4] (Liu et al., 2010). The values of the bond angles around the cadmium atoms are close to those expected for a regular octahedral geometry, the largest deviation being observed for the N8—Cd1—N5 angle [91.68 (8)°]. Weak O—H···Cl interactions (Table 1) contribute to the stability of the crystal packing (Fig. 2).

Experimental

An aqueous solution (15 ml) of CdCl2.2.5H2O (0.23 g, 1.0 mmol) was added slowly with constant stirring to a solution of 1,1'-(2,2'-oxybis(ethane-2,1-diyl))bis(1H-imidazole)) (0.21 g, 0.1 mmol) in water (20 ml). The reaction mixture was then heated to reflux for 3 h. The resulting mixture was left to stand at room temperature for three weeks. Colourless block crystals suitable for X-ray analysis were obtained on slow evaporation of the solvent. Yield: 67% (based on Cd).

Refinement

The water H atoms were located in a difference Fourier map and refined with the O—H bond distances restrained to 0.86 Å. All other H atoms were positioned geometrically, with C—H = 0.93–0.97 Å, and constrained to ride on their parent atoms, with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms are omitted for clarity.
Fig. 2.
Packing diagram of the title compound viewed along the b axis. Hydrogen bonds are shown as dashed lines.

Crystal data

[CdCl2(C12H18N4O2)2]·H2OF(000) = 1440
Mr = 701.92Dx = 1.523 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9598 reflections
a = 15.3629 (13) Åθ = 2.2–27.2°
b = 11.0659 (9) ŵ = 0.94 mm1
c = 18.4492 (16) ÅT = 293 K
β = 102.558 (1)°Block, colorless
V = 3061.4 (4) Å30.26 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer5691 independent reflections
Radiation source: sealed tube4148 reflections with I > 2σ(I)
graphiteRint = 0.022
phi and ω scansθmax = 25.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −18→18
Tmin = 0.793, Tmax = 0.835k = −13→13
21862 measured reflectionsl = −22→22

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.030Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H atoms treated by a mixture of independent and constrained refinement
S = 1.04w = 1/[σ2(Fo2) + (0.0331P)2 + 3.6911P] where P = (Fo2 + 2Fc2)/3
5691 reflections(Δ/σ)max < 0.001
372 parametersΔρmax = 0.53 e Å3
8 restraintsΔρmin = −0.38 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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)

xyzUiso*/Ueq
Cd10.50000.00000.50000.03408 (9)
Cd20.00000.50000.50000.03731 (10)
Cl10.35374 (6)0.07994 (8)0.40345 (5)0.0623 (3)
Cl2−0.14291 (6)0.51856 (10)0.38908 (5)0.0654 (3)
N10.06622 (17)0.6671 (2)0.45294 (15)0.0453 (6)
N20.1595 (2)0.7621 (3)0.39710 (16)0.0555 (7)
N30.0872 (3)0.2692 (3)0.3298 (2)0.0799 (11)
N40.06263 (18)0.3669 (3)0.42699 (17)0.0508 (7)
N50.58186 (17)0.1608 (2)0.46622 (14)0.0398 (6)
N60.61728 (16)0.3470 (2)0.44305 (13)0.0373 (6)
N70.48013 (18)0.2327 (2)0.69235 (13)0.0394 (6)
N80.46279 (17)0.1245 (2)0.59039 (13)0.0386 (6)
O10.1550 (2)0.6593 (3)0.25676 (15)0.0883 (10)
O20.1213 (4)0.4214 (4)0.2164 (2)0.148 (2)
O30.60598 (15)0.42888 (19)0.70446 (12)0.0457 (5)
O40.62769 (15)0.51267 (18)0.56526 (12)0.0456 (5)
O1W0.6777 (2)0.5003 (4)0.26691 (19)0.0850 (10)
C10.6641 (2)0.1620 (3)0.44932 (19)0.0488 (8)
H10.69930.09400.44760.059*
C20.6870 (2)0.2762 (3)0.43540 (18)0.0460 (8)
H20.73980.30120.42310.055*
C30.5561 (2)0.2744 (3)0.46206 (16)0.0392 (7)
H30.50210.30100.47120.047*
C40.6131 (2)0.4790 (3)0.43723 (17)0.0444 (8)
H4A0.55150.50490.43040.053*
H4B0.63480.50430.39400.053*
C50.6676 (2)0.5382 (3)0.50518 (17)0.0436 (7)
H5A0.72810.50730.51520.052*
H5B0.66970.62480.49770.052*
C60.6773 (2)0.5605 (3)0.63323 (17)0.0454 (8)
H6A0.69210.64440.62670.055*
H6B0.73240.51560.64910.055*
C70.6227 (2)0.5509 (3)0.68994 (18)0.0472 (8)
H7A0.65380.58950.73540.057*
H7B0.56660.59270.67260.057*
C80.5455 (2)0.4203 (3)0.75265 (17)0.0462 (8)
H8A0.49130.46430.73180.055*
H8B0.57200.45550.80050.055*
C90.5243 (2)0.2903 (3)0.76207 (16)0.0499 (8)
H9A0.57910.24720.78260.060*
H9B0.48600.28410.79740.060*
C100.5194 (2)0.1621 (3)0.65024 (16)0.0408 (7)
H100.57960.14180.66180.049*
C110.3925 (2)0.2424 (3)0.65710 (17)0.0442 (8)
H110.34850.28630.67290.053*
C120.3827 (2)0.1752 (3)0.59443 (17)0.0416 (7)
H120.32960.16510.55950.050*
C130.0398 (3)0.3551 (4)0.3545 (2)0.0640 (10)
H13−0.00410.40100.32400.077*
C140.1286 (2)0.2831 (3)0.4502 (3)0.0665 (11)
H140.15800.26960.49910.080*
C150.1439 (3)0.2235 (4)0.3904 (4)0.0868 (16)
H150.18560.16240.39060.104*
C160.0786 (4)0.2352 (6)0.2505 (3)0.131 (3)
H16A0.10190.15400.24900.157*
H16B0.01560.23240.22730.157*
C170.1193 (6)0.3070 (6)0.2090 (3)0.139 (3)
H17A0.18070.28000.21690.167*
H17B0.09200.29030.15750.167*
C180.1213 (7)0.5041 (6)0.1698 (3)0.153 (3)
H18A0.06040.50980.14160.184*
H18B0.15610.47350.13580.184*
C190.1489 (4)0.6200 (5)0.1849 (3)0.0984 (16)
H19A0.10810.67300.15200.118*
H19B0.20710.62900.17300.118*
C200.1985 (3)0.7675 (4)0.2759 (2)0.0749 (12)
H20A0.15800.83380.25850.090*
H20B0.24850.77380.25180.090*
C210.2309 (3)0.7774 (4)0.3559 (2)0.0711 (11)
H21A0.25830.85610.36750.085*
H21B0.27630.71660.37230.085*
C220.1212 (3)0.8467 (3)0.4339 (2)0.0635 (10)
H220.13210.92950.43520.076*
C230.1232 (2)0.6563 (3)0.40966 (19)0.0506 (8)
H230.13690.58320.38990.061*
C240.0646 (2)0.7880 (3)0.4682 (2)0.0588 (9)
H240.02990.82410.49760.071*
H1WA0.678 (5)0.550 (6)0.230 (3)0.19 (3)*
H1WB0.7311 (18)0.505 (5)0.292 (3)0.12 (2)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.04100 (18)0.02596 (15)0.03493 (17)−0.00286 (12)0.00747 (13)−0.00432 (12)
Cd20.03589 (17)0.04115 (18)0.03550 (17)−0.00300 (13)0.00907 (13)0.00258 (13)
Cl10.0565 (5)0.0578 (5)0.0629 (5)0.0116 (4)−0.0079 (4)−0.0091 (4)
Cl20.0485 (5)0.0866 (7)0.0535 (5)−0.0051 (5)−0.0056 (4)0.0107 (5)
N10.0415 (15)0.0459 (15)0.0483 (15)−0.0039 (12)0.0091 (12)0.0062 (13)
N20.0594 (19)0.0520 (17)0.0558 (18)−0.0209 (15)0.0145 (15)0.0010 (14)
N30.091 (3)0.061 (2)0.107 (3)−0.018 (2)0.062 (2)−0.030 (2)
N40.0454 (16)0.0502 (16)0.0607 (18)−0.0017 (13)0.0199 (14)−0.0053 (14)
N50.0420 (14)0.0334 (13)0.0442 (14)−0.0046 (11)0.0096 (12)−0.0012 (11)
N60.0453 (15)0.0339 (13)0.0328 (13)−0.0049 (11)0.0086 (11)0.0011 (10)
N70.0552 (17)0.0327 (13)0.0325 (13)−0.0055 (12)0.0142 (12)−0.0016 (10)
N80.0483 (15)0.0322 (13)0.0361 (13)−0.0023 (11)0.0112 (12)−0.0025 (11)
O10.111 (2)0.103 (2)0.0575 (17)−0.053 (2)0.0321 (16)−0.0108 (16)
O20.293 (6)0.086 (3)0.085 (3)−0.037 (3)0.083 (3)−0.021 (2)
O30.0581 (14)0.0379 (12)0.0451 (12)−0.0010 (10)0.0197 (11)−0.0046 (10)
O40.0514 (13)0.0461 (13)0.0399 (12)−0.0151 (10)0.0112 (10)−0.0070 (10)
O1W0.0576 (19)0.133 (3)0.0605 (19)0.0083 (19)0.0039 (16)−0.016 (2)
C10.0482 (19)0.0413 (18)0.058 (2)0.0046 (15)0.0131 (16)−0.0043 (16)
C20.0413 (18)0.0467 (18)0.053 (2)−0.0050 (15)0.0175 (15)−0.0033 (15)
C30.0403 (17)0.0369 (16)0.0419 (17)−0.0026 (13)0.0121 (14)0.0008 (13)
C40.059 (2)0.0336 (16)0.0378 (17)−0.0056 (14)0.0052 (15)0.0076 (13)
C50.054 (2)0.0332 (15)0.0440 (18)−0.0085 (14)0.0118 (15)0.0051 (14)
C60.0509 (19)0.0383 (17)0.0449 (18)−0.0109 (15)0.0057 (15)−0.0062 (14)
C70.054 (2)0.0383 (17)0.0477 (19)−0.0041 (15)0.0081 (16)−0.0113 (15)
C80.061 (2)0.0445 (18)0.0348 (16)−0.0075 (16)0.0136 (15)−0.0097 (14)
C90.073 (2)0.0488 (19)0.0286 (16)−0.0135 (17)0.0135 (15)−0.0028 (14)
C100.0435 (17)0.0406 (17)0.0397 (17)−0.0043 (14)0.0117 (14)−0.0021 (14)
C110.060 (2)0.0324 (16)0.0443 (18)0.0069 (15)0.0204 (16)−0.0002 (14)
C120.0473 (18)0.0330 (16)0.0422 (17)0.0031 (14)0.0049 (14)0.0038 (13)
C130.069 (3)0.059 (2)0.068 (3)−0.004 (2)0.026 (2)−0.015 (2)
C140.046 (2)0.053 (2)0.102 (3)0.0028 (18)0.021 (2)0.006 (2)
C150.066 (3)0.049 (2)0.162 (5)−0.003 (2)0.061 (3)−0.020 (3)
C160.169 (6)0.119 (5)0.140 (5)−0.065 (4)0.110 (5)−0.085 (4)
C170.235 (8)0.112 (5)0.068 (4)−0.037 (5)0.028 (4)−0.029 (3)
C180.268 (10)0.119 (6)0.057 (3)−0.041 (6)0.003 (5)−0.014 (3)
C190.138 (5)0.107 (4)0.060 (3)−0.013 (4)0.042 (3)0.001 (3)
C200.074 (3)0.077 (3)0.080 (3)−0.019 (2)0.031 (2)0.010 (2)
C210.066 (3)0.073 (3)0.080 (3)−0.026 (2)0.028 (2)0.000 (2)
C220.069 (3)0.043 (2)0.075 (3)−0.0130 (19)0.008 (2)0.0078 (19)
C230.050 (2)0.0487 (19)0.055 (2)−0.0121 (16)0.0150 (17)0.0019 (16)
C240.058 (2)0.051 (2)0.069 (2)−0.0039 (18)0.0163 (19)−0.0040 (18)

Geometric parameters (Å, °)

Cd1—N82.328 (2)C2—H20.9300
Cd1—N8i2.328 (2)C3—H30.9300
Cd1—N52.340 (2)C4—C51.499 (4)
Cd1—N5i2.340 (2)C4—H4A0.9700
Cd1—Cl12.6951 (9)C4—H4B0.9700
Cd1—Cl1i2.6952 (9)C5—H5A0.9700
Cd2—N4ii2.339 (3)C5—H5B0.9700
Cd2—N42.339 (3)C6—C71.480 (4)
Cd2—N12.365 (3)C6—H6A0.9700
Cd2—N1ii2.365 (3)C6—H6B0.9700
Cd2—Cl22.6639 (9)C7—H7A0.9700
Cd2—Cl2ii2.6639 (9)C7—H7B0.9700
N1—C231.313 (4)C8—C91.493 (4)
N1—C241.368 (4)C8—H8A0.9700
N2—C231.338 (4)C8—H8B0.9700
N2—C221.363 (5)C9—H9A0.9700
N2—C211.473 (4)C9—H9B0.9700
N3—C131.337 (5)C10—H100.9300
N3—C151.357 (6)C11—C121.355 (4)
N3—C161.487 (6)C11—H110.9300
N4—C131.313 (5)C12—H120.9300
N4—C141.372 (5)C13—H130.9300
N5—C31.315 (4)C14—C151.350 (6)
N5—C11.366 (4)C14—H140.9300
N6—C31.340 (4)C15—H150.9300
N6—C21.360 (4)C16—C171.348 (7)
N6—C41.464 (4)C16—H16A0.9700
N7—C101.335 (4)C16—H16B0.9700
N7—C111.366 (4)C17—H17A0.9700
N7—C91.464 (4)C17—H17B0.9700
N8—C101.316 (4)C18—C191.360 (7)
N8—C121.370 (4)C18—H18A0.9700
O1—C191.378 (5)C18—H18B0.9700
O1—C201.379 (5)C19—H19A0.9700
O2—C181.256 (7)C19—H19B0.9700
O2—C171.273 (7)C20—C211.456 (6)
O3—C71.411 (4)C20—H20A0.9700
O3—C81.422 (4)C20—H20B0.9700
O4—C51.407 (4)C21—H21A0.9700
O4—C61.420 (4)C21—H21B0.9700
O1W—H1WA0.88 (6)C22—C241.348 (5)
O1W—H1WB0.85 (2)C22—H220.9300
C1—C21.351 (4)C23—H230.9300
C1—H10.9300C24—H240.9300
N8—Cd1—N8i180.00 (9)C7—C6—H6B110.0
N8—Cd1—N588.32 (8)H6A—C6—H6B108.3
N8i—Cd1—N591.68 (8)O3—C7—C6110.9 (3)
N8—Cd1—N5i91.68 (8)O3—C7—H7A109.5
N8i—Cd1—N5i88.32 (8)C6—C7—H7A109.5
N5—Cd1—N5i180.0O3—C7—H7B109.5
N8—Cd1—Cl188.85 (7)C6—C7—H7B109.5
N8i—Cd1—Cl191.15 (7)H7A—C7—H7B108.0
N5—Cd1—Cl189.63 (7)O3—C8—C9109.0 (3)
N5i—Cd1—Cl190.37 (7)O3—C8—H8A109.9
N8—Cd1—Cl1i91.15 (7)C9—C8—H8A109.9
N8i—Cd1—Cl1i88.85 (7)O3—C8—H8B109.9
N5—Cd1—Cl1i90.37 (7)C9—C8—H8B109.9
N5i—Cd1—Cl1i89.63 (7)H8A—C8—H8B108.3
Cl1—Cd1—Cl1i180.0N7—C9—C8112.9 (2)
N4ii—Cd2—N4179.999 (1)N7—C9—H9A109.0
N4ii—Cd2—N189.01 (10)C8—C9—H9A109.0
N4—Cd2—N190.99 (10)N7—C9—H9B109.0
N4ii—Cd2—N1ii90.99 (10)C8—C9—H9B109.0
N4—Cd2—N1ii89.01 (10)H9A—C9—H9B107.8
N1—Cd2—N1ii180.0N8—C10—N7111.9 (3)
N4ii—Cd2—Cl291.17 (8)N8—C10—H10124.1
N4—Cd2—Cl288.84 (8)N7—C10—H10124.1
N1—Cd2—Cl290.36 (7)C12—C11—N7106.2 (3)
N1ii—Cd2—Cl289.65 (7)C12—C11—H11126.9
N4ii—Cd2—Cl2ii88.83 (8)N7—C11—H11126.9
N4—Cd2—Cl2ii91.17 (8)C11—C12—N8109.7 (3)
N1—Cd2—Cl2ii89.64 (7)C11—C12—H12125.2
N1ii—Cd2—Cl2ii90.35 (7)N8—C12—H12125.2
Cl2—Cd2—Cl2ii179.999 (1)N4—C13—N3112.0 (4)
C23—N1—C24105.0 (3)N4—C13—H13124.0
C23—N1—Cd2123.3 (2)N3—C13—H13124.0
C24—N1—Cd2131.4 (2)C15—C14—N4108.9 (4)
C23—N2—C22105.9 (3)C15—C14—H14125.5
C23—N2—C21125.1 (3)N4—C14—H14125.5
C22—N2—C21128.9 (3)C14—C15—N3107.2 (4)
C13—N3—C15106.5 (4)C14—C15—H15126.4
C13—N3—C16125.2 (5)N3—C15—H15126.4
C15—N3—C16128.3 (5)C17—C16—N3117.2 (5)
C13—N4—C14105.4 (3)C17—C16—H16A108.0
C13—N4—Cd2126.7 (3)N3—C16—H16A108.0
C14—N4—Cd2127.9 (3)C17—C16—H16B108.0
C3—N5—C1105.0 (3)N3—C16—H16B108.0
C3—N5—Cd1124.8 (2)H16A—C16—H16B107.3
C1—N5—Cd1130.2 (2)O2—C17—C16121.9 (6)
C3—N6—C2107.1 (3)O2—C17—H17A106.9
C3—N6—C4126.5 (3)C16—C17—H17A106.9
C2—N6—C4126.2 (3)O2—C17—H17B106.9
C10—N7—C11107.0 (2)C16—C17—H17B106.9
C10—N7—C9125.8 (3)H17A—C17—H17B106.7
C11—N7—C9127.2 (3)O2—C18—C19126.4 (5)
C10—N8—C12105.2 (2)O2—C18—H18A105.7
C10—N8—Cd1124.6 (2)C19—C18—H18A105.7
C12—N8—Cd1130.2 (2)O2—C18—H18B105.7
C19—O1—C20116.7 (3)C19—C18—H18B105.7
C18—O2—C17130.9 (5)H18A—C18—H18B106.2
C7—O3—C8110.7 (2)C18—C19—O1116.6 (5)
C5—O4—C6112.2 (2)C18—C19—H19A108.1
H1WA—O1W—H1WB102 (6)O1—C19—H19A108.1
C2—C1—N5110.1 (3)C18—C19—H19B108.1
C2—C1—H1124.9O1—C19—H19B108.1
N5—C1—H1124.9H19A—C19—H19B107.3
C1—C2—N6106.0 (3)O1—C20—C21111.4 (3)
C1—C2—H2127.0O1—C20—H20A109.3
N6—C2—H2127.0C21—C20—H20A109.3
N5—C3—N6111.7 (3)O1—C20—H20B109.3
N5—C3—H3124.1C21—C20—H20B109.3
N6—C3—H3124.1H20A—C20—H20B108.0
N6—C4—C5111.5 (3)C20—C21—N2112.7 (3)
N6—C4—H4A109.3C20—C21—H21A109.1
C5—C4—H4A109.3N2—C21—H21A109.1
N6—C4—H4B109.3C20—C21—H21B109.1
C5—C4—H4B109.3N2—C21—H21B109.1
H4A—C4—H4B108.0H21A—C21—H21B107.8
O4—C5—C4108.1 (2)C24—C22—N2107.1 (3)
O4—C5—H5A110.1C24—C22—H22126.4
C4—C5—H5A110.1N2—C22—H22126.4
O4—C5—H5B110.1N1—C23—N2112.5 (3)
C4—C5—H5B110.1N1—C23—H23123.7
H5A—C5—H5B108.4N2—C23—H23123.7
O4—C6—C7108.7 (3)C22—C24—N1109.4 (3)
O4—C6—H6A110.0C22—C24—H24125.3
C7—C6—H6A110.0N1—C24—H24125.3
O4—C6—H6B110.0
N4ii—Cd2—N1—C23173.1 (3)C5—O4—C6—C7169.1 (3)
N4—Cd2—N1—C23−6.9 (3)C8—O3—C7—C6−173.5 (3)
Cl2—Cd2—N1—C23−95.8 (3)O4—C6—C7—O364.0 (3)
Cl2ii—Cd2—N1—C2384.2 (3)C7—O3—C8—C9175.8 (3)
N4ii—Cd2—N1—C241.1 (3)C10—N7—C9—C8100.1 (4)
N4—Cd2—N1—C24−178.9 (3)C11—N7—C9—C8−78.3 (4)
Cl2—Cd2—N1—C2492.3 (3)O3—C8—C9—N7−62.2 (4)
Cl2ii—Cd2—N1—C24−87.7 (3)C12—N8—C10—N70.5 (3)
N1—Cd2—N4—C13−70.7 (3)Cd1—N8—C10—N7179.79 (18)
N1ii—Cd2—N4—C13109.3 (3)C11—N7—C10—N8−0.6 (3)
Cl2—Cd2—N4—C1319.7 (3)C9—N7—C10—N8−179.3 (3)
Cl2ii—Cd2—N4—C13−160.3 (3)C10—N7—C11—C120.4 (3)
N1—Cd2—N4—C14111.2 (3)C9—N7—C11—C12179.1 (3)
N1ii—Cd2—N4—C14−68.8 (3)N7—C11—C12—N8−0.1 (3)
Cl2—Cd2—N4—C14−158.5 (3)C10—N8—C12—C11−0.2 (3)
Cl2ii—Cd2—N4—C1421.5 (3)Cd1—N8—C12—C11−179.4 (2)
N8—Cd1—N5—C3−40.5 (3)C14—N4—C13—N3−0.2 (4)
N8i—Cd1—N5—C3139.5 (3)Cd2—N4—C13—N3−178.7 (2)
Cl1—Cd1—N5—C348.4 (2)C15—N3—C13—N4−0.1 (5)
Cl1i—Cd1—N5—C3−131.6 (2)C16—N3—C13—N4−178.9 (4)
N8—Cd1—N5—C1137.2 (3)C13—N4—C14—C150.4 (4)
N8i—Cd1—N5—C1−42.8 (3)Cd2—N4—C14—C15178.8 (2)
Cl1—Cd1—N5—C1−133.9 (3)N4—C14—C15—N3−0.4 (5)
Cl1i—Cd1—N5—C146.1 (3)C13—N3—C15—C140.3 (5)
N5—Cd1—N8—C10−68.9 (2)C16—N3—C15—C14179.1 (4)
N5i—Cd1—N8—C10111.1 (2)C13—N3—C16—C1779.4 (8)
Cl1—Cd1—N8—C10−158.6 (2)C15—N3—C16—C17−99.2 (8)
Cl1i—Cd1—N8—C1021.4 (2)C18—O2—C17—C16−147.6 (9)
N5—Cd1—N8—C12110.1 (2)N3—C16—C17—O2−38.2 (12)
N5i—Cd1—N8—C12−69.9 (2)C17—O2—C18—C19−159.6 (9)
Cl1—Cd1—N8—C1220.5 (2)O2—C18—C19—O1−18.3 (14)
Cl1i—Cd1—N8—C12−159.5 (2)C20—O1—C19—C18168.1 (6)
C3—N5—C1—C20.2 (4)C19—O1—C20—C21−158.1 (4)
Cd1—N5—C1—C2−177.9 (2)O1—C20—C21—N2−55.9 (5)
N5—C1—C2—N6−0.6 (4)C23—N2—C21—C2076.6 (5)
C3—N6—C2—C10.8 (4)C22—N2—C21—C20−108.3 (5)
C4—N6—C2—C1176.5 (3)C23—N2—C22—C241.0 (4)
C1—N5—C3—N60.4 (3)C21—N2—C22—C24−174.8 (4)
Cd1—N5—C3—N6178.53 (18)C24—N1—C23—N21.0 (4)
C2—N6—C3—N5−0.8 (3)Cd2—N1—C23—N2−172.7 (2)
C4—N6—C3—N5−176.5 (3)C22—N2—C23—N1−1.3 (4)
C3—N6—C4—C599.4 (4)C21—N2—C23—N1174.7 (3)
C2—N6—C4—C5−75.5 (4)N2—C22—C24—N1−0.4 (4)
C6—O4—C5—C4177.2 (3)C23—N1—C24—C22−0.3 (4)
N6—C4—C5—O4−66.5 (3)Cd2—N1—C24—C22172.7 (2)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1W—H1WB···Cl2iii0.85 (2)2.33 (3)3.165 (3)164 (5)
O1W—H1WA···Cl1iv0.88 (6)2.42 (5)3.198 (4)147 (7)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2451).

References

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  • Liu, Y. Y., Ma, J. F., Yang, J. & Su, Z. M. (2007). Cryst. Growth Des.7, 3027–3037.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wen, L. L., Lu, Z. D., Lin, J. G., Tian, Z. F., Zhu, H. Z. & Meng, Q. J. (2007). Cryst. Growth Des.7, 93–99.

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