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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): m1409–m1410.
Published online 2009 October 23. doi:  10.1107/S1600536809042044
PMCID: PMC2971083

Di-μ-chlorido-bis­[(2′-carb­oxybiphen­yl-2-carboxyl­ato-κO)(2,2′:6′,2′′-terpyridine-κ3 N,N′,N′′)cadmium(II)] hemihydrate

Abstract

In the centrosymmetric dinuclear title compound, [Cd2(C14H9O4)2Cl2(C15H11N3)2]·0.5H2O, each of the CdII ions is coordinated by three N atoms from a chelating 2,2′:6′,2′′-terpyridine ligand, two bridging Cl atoms and one O atom of a 2′-carb­oxy-[1,1′-biphen­yl]-2-carboxyl­ate anion. The coordination environment is distorted octa­hedral. In the crystal, inter­molecular O—H(...)O hydrogen bonds link symmetry-related mol­ecules, forming an infinite chain. The half-occupancy water mol­ecule is disordered over two general sites with 0.25 occupancy and is, in turn, disordered over an inversion center.

Related literature

For background chemistry, see: Meng et al. (2004 [triangle]). For related structures, see: Liu (2009 [triangle]); Xian et al. (2008 [triangle]); Qu & Li (2008 [triangle]); Han et al. (2008 [triangle]); Du et al. (2008 [triangle]); Wang et al. (2008 [triangle]); Kurawa et al. (2008 [triangle]); An et al. (2009 [triangle]); Seidel & Oppel (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1409-scheme1.jpg

Experimental

Crystal data

  • [Cd2(C14H9O4)2Cl2(C15H11N3)2]·0.5H2O
  • M r = 1253.67
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1409-efi1.jpg
  • a = 9.5673 (18) Å
  • b = 11.575 (2) Å
  • c = 12.565 (2) Å
  • α = 96.233 (4)°
  • β = 96.927 (4)°
  • γ = 108.132 (3)°
  • V = 1297.0 (4) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 0.99 mm−1
  • T = 296 K
  • 0.28 × 0.26 × 0.24 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.770, T max = 0.798
  • 7084 measured reflections
  • 4529 independent reflections
  • 3969 reflections with I > 2σ(I)
  • R int = 0.059

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.124
  • S = 1.01
  • 4529 reflections
  • 353 parameters
  • H-atom parameters constrained
  • Δρmax = 1.33 e Å−3
  • Δρmin = −0.98 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg & Putz, 1999 [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/S1600536809042044/nk2006sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042044/nk2006Isup2.hkl

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

supplementary crystallographic information

Comment

Various coordination modes and potential applications in catalysis, fluorescent materials, NLO materials and so on (Meng et al. 2004) have been described. Here we report the crystal structure of the title complex prepared from CdCl2 and 2'-carboxy-[1,1'-biphenyl]-2-carboxylate ligand (see experimental).

In the centrosymmetric dinuclear title compound, showing in Fig. 1, each of the CdII ions is coordinated by three N atoms from a chelating 2,2':6',2''-terpyridine ligand, two bridging Cl atoms and one O atom of a 2'-carboxy-[1,1'-biphenyl]-2-carboxylate anion. The coordination environment is distorted octahedral. In the dimeric structure, two CdII ions are bridged through the Cl atoms, resulting in a planar Cd2Cl2 core. One of the bridging Cd—Cl bonds is significantly longer than the other. The half-occupancy water molecule is disordered over two general sites with occupancies of 0.25 and 0.25, and is, in turn, disordered over an inversion center.

In the crystal packing, the complex molecules are linked into a one-dimensional infinite chain links supramolecular structure (Fig. 2) by intra- and intermolecular O—H···O, C—H···O and C—H···Cl hydrogen bonding interactions involving the solvent water molecules, the carboxyl group. groups and the chloride (Table 1).

Experimental

The title complound was synthesized hydrothermally in a Teflon-lined autoclave (25 ml) by heating a mixture of [1,1'-biphenyl]-2,2'-dicarboxylic acid (0.2 mmol), 2,2':6',2''-terpyridine (0.4 mmol) and CdCl2.2.5H2O (0.2 mmol) in water (10 ml) at 393 K for 3 d. Crystals suitable for X-ray analysis were obtained.

Refinement

All H atoms were included in calculated positions, with C—H bond lengths fixed at 0.92 Å (carboxyl –COOH), 0.93Å (aryl group) and O—H = 0.85 Å and were refined in the riding-model approximation. Uiso(H) values were calculated at 1.5 Ueq(C) for carboxyl groups and 1.2 Ueq(C) otherwise.

Figures

Fig. 1.
The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as small spheres of arbitrary radius.
Fig. 2.
Crystal packing of the title complound. Hydrogen-bond interactions are drawn with dashed lines.

Crystal data

[Cd2(C14H9O4)2Cl2(C15H11N3)2]·0.5H2OZ = 1
Mr = 1253.67F(000) = 629
Triclinic, P1Dx = 1.605 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5673 (18) ÅCell parameters from 4272 reflections
b = 11.575 (2) Åθ = 3.0–27.8°
c = 12.565 (2) ŵ = 0.99 mm1
α = 96.233 (4)°T = 296 K
β = 96.927 (4)°Block, colourless
γ = 108.132 (3)°0.28 × 0.26 × 0.24 mm
V = 1297.0 (4) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer4529 independent reflections
Radiation source: sealed tube3969 reflections with I > 2σ(I)
graphiteRint = 0.059
ω scansθmax = 25.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→6
Tmin = 0.770, Tmax = 0.798k = −11→13
7084 measured reflectionsl = −13→14

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0854P)2] where P = (Fo2 + 2Fc2)/3
4529 reflections(Δ/σ)max = 0.001
353 parametersΔρmax = 1.33 e Å3
0 restraintsΔρmin = −0.98 e Å3

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)

xyzUiso*/UeqOcc. (<1)
Cd10.89580 (3)0.91082 (2)0.60537 (2)0.03337 (14)
Cl11.04993 (13)0.86663 (10)0.46861 (10)0.0456 (3)
N11.0075 (4)1.0318 (3)0.7764 (3)0.0380 (8)
N20.7167 (4)0.9594 (3)0.6971 (3)0.0315 (7)
N30.6578 (4)0.8338 (3)0.4963 (3)0.0379 (8)
O10.8489 (4)0.7257 (3)0.6690 (3)0.0480 (7)
O21.0910 (4)0.7855 (3)0.7351 (2)0.0473 (7)
O31.2591 (4)0.7729 (3)0.8974 (2)0.0490 (8)
H3A1.20600.76910.83990.073*
O41.4450 (4)0.7087 (4)0.9518 (3)0.0715 (11)
C10.9344 (5)0.5939 (3)0.7723 (3)0.0359 (9)
C20.8088 (5)0.5557 (4)0.8212 (3)0.0446 (10)
H20.73800.59540.81370.054*
C30.7870 (6)0.4608 (4)0.8802 (4)0.0500 (12)
H30.70360.43810.91420.060*
C40.8886 (6)0.3989 (4)0.8894 (4)0.0532 (13)
H40.87490.33520.93040.064*
C51.0103 (6)0.4316 (4)0.8374 (4)0.0480 (11)
H51.07610.38700.84140.058*
C61.0381 (5)0.5304 (3)0.7786 (3)0.0362 (9)
C71.1713 (5)0.5553 (3)0.7216 (3)0.0369 (9)
C81.3159 (5)0.6283 (4)0.7719 (3)0.0387 (9)
C91.4367 (5)0.6326 (4)0.7207 (4)0.0503 (11)
H91.53220.67860.75620.060*
C101.4179 (7)0.5693 (5)0.6174 (5)0.0644 (15)
H101.49980.57420.58280.077*
C111.2763 (7)0.4989 (5)0.5660 (4)0.0659 (15)
H111.26270.45680.49610.079*
C121.1544 (6)0.4905 (4)0.6176 (4)0.0484 (11)
H121.05990.44100.58270.058*
C130.9598 (5)0.7096 (4)0.7199 (3)0.0379 (9)
C141.3450 (5)0.7058 (4)0.8823 (4)0.0458 (11)
C151.1542 (6)1.0720 (4)0.8099 (4)0.0524 (12)
H151.21471.05210.76340.063*
C161.2213 (6)1.1415 (5)0.9098 (5)0.0651 (15)
H161.32441.16900.92990.078*
C171.1310 (7)1.1688 (5)0.9785 (5)0.0679 (16)
H171.17231.21391.04720.081*
C180.9788 (6)1.1290 (4)0.9454 (4)0.0549 (12)
H180.91681.14720.99140.066*
C190.9188 (5)1.0611 (3)0.8423 (3)0.0379 (9)
C200.7568 (5)1.0186 (3)0.7991 (3)0.0360 (9)
C210.6505 (6)1.0399 (4)0.8586 (4)0.0490 (11)
H210.67861.08240.92910.059*
C220.5042 (6)0.9969 (4)0.8106 (4)0.0582 (13)
H220.43201.00880.84990.070*
C230.4613 (5)0.9365 (4)0.7058 (4)0.0504 (12)
H230.36170.90820.67320.060*
C240.5730 (4)0.9188 (3)0.6493 (4)0.0367 (9)
C250.5410 (4)0.8528 (3)0.5354 (3)0.0370 (9)
C260.3985 (5)0.8115 (4)0.4741 (4)0.0545 (12)
H260.31910.82620.50240.065*
C270.3772 (6)0.7487 (5)0.3713 (5)0.0657 (15)
H270.28280.72020.32930.079*
C280.4959 (6)0.7279 (5)0.3300 (4)0.0609 (14)
H280.48330.68600.26020.073*
C290.6342 (6)0.7711 (4)0.3953 (4)0.0498 (11)
H290.71440.75630.36840.060*
O1W0.4261 (19)0.4352 (14)0.9220 (13)0.082 (5)0.25
H1WA0.40410.40790.98010.099*0.25
H1WB0.39280.49430.91410.099*0.25

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.0282 (2)0.0394 (2)0.0330 (2)0.01333 (13)0.00468 (13)0.00142 (13)
Cl10.0510 (7)0.0417 (5)0.0576 (7)0.0264 (5)0.0265 (5)0.0117 (5)
N10.037 (2)0.0405 (18)0.0375 (18)0.0179 (15)0.0011 (15)−0.0009 (14)
N20.0292 (18)0.0307 (16)0.0391 (18)0.0148 (13)0.0105 (14)0.0045 (13)
N30.0338 (19)0.0389 (18)0.0416 (19)0.0134 (15)0.0049 (15)0.0054 (15)
O10.0488 (19)0.0480 (17)0.0532 (19)0.0249 (15)0.0036 (15)0.0120 (14)
O20.049 (2)0.0382 (15)0.0574 (19)0.0157 (14)0.0107 (15)0.0130 (14)
O30.052 (2)0.0532 (18)0.0356 (16)0.0137 (16)0.0057 (14)−0.0074 (14)
O40.056 (2)0.085 (3)0.058 (2)0.010 (2)−0.0181 (18)0.0130 (19)
C10.039 (2)0.0345 (19)0.031 (2)0.0106 (17)−0.0013 (17)0.0006 (16)
C20.040 (3)0.049 (2)0.042 (2)0.014 (2)0.0034 (19)0.0007 (19)
C30.045 (3)0.051 (3)0.042 (3)−0.001 (2)0.007 (2)0.006 (2)
C40.062 (3)0.043 (2)0.048 (3)0.006 (2)0.005 (2)0.016 (2)
C50.058 (3)0.038 (2)0.047 (3)0.014 (2)0.003 (2)0.0102 (19)
C60.039 (2)0.0317 (19)0.033 (2)0.0102 (17)−0.0032 (17)0.0005 (16)
C70.046 (3)0.0321 (19)0.036 (2)0.0194 (18)0.0039 (18)0.0052 (16)
C80.041 (2)0.036 (2)0.043 (2)0.0174 (18)0.0052 (19)0.0100 (17)
C90.041 (3)0.047 (2)0.070 (3)0.022 (2)0.012 (2)0.015 (2)
C100.074 (4)0.057 (3)0.079 (4)0.034 (3)0.037 (3)0.012 (3)
C110.091 (5)0.058 (3)0.058 (3)0.036 (3)0.029 (3)−0.007 (2)
C120.057 (3)0.043 (2)0.044 (2)0.021 (2)0.002 (2)−0.0056 (19)
C130.046 (3)0.040 (2)0.032 (2)0.020 (2)0.0075 (18)0.0031 (17)
C140.043 (3)0.048 (2)0.037 (2)0.003 (2)0.001 (2)0.0098 (19)
C150.044 (3)0.055 (3)0.055 (3)0.021 (2)−0.005 (2)−0.007 (2)
C160.047 (3)0.057 (3)0.078 (4)0.019 (2)−0.024 (3)−0.020 (3)
C170.075 (4)0.059 (3)0.061 (3)0.035 (3)−0.026 (3)−0.023 (3)
C180.068 (3)0.055 (3)0.044 (3)0.033 (3)−0.002 (2)−0.008 (2)
C190.049 (3)0.0319 (19)0.036 (2)0.0203 (18)0.0048 (19)0.0027 (16)
C200.043 (2)0.0335 (19)0.036 (2)0.0175 (17)0.0098 (18)0.0083 (16)
C210.057 (3)0.052 (3)0.047 (3)0.027 (2)0.022 (2)0.005 (2)
C220.058 (3)0.058 (3)0.070 (3)0.027 (2)0.035 (3)0.009 (3)
C230.030 (2)0.056 (3)0.070 (3)0.019 (2)0.018 (2)0.007 (2)
C240.032 (2)0.0327 (19)0.050 (2)0.0146 (16)0.0097 (18)0.0098 (17)
C250.031 (2)0.0304 (19)0.050 (2)0.0097 (16)0.0021 (18)0.0116 (17)
C260.034 (3)0.058 (3)0.072 (3)0.020 (2)−0.003 (2)0.007 (2)
C270.042 (3)0.071 (3)0.067 (4)0.009 (2)−0.018 (3)−0.001 (3)
C280.056 (3)0.058 (3)0.053 (3)0.011 (2)−0.012 (2)−0.010 (2)
C290.048 (3)0.051 (3)0.048 (3)0.019 (2)−0.002 (2)−0.004 (2)
O1W0.094 (13)0.085 (11)0.094 (12)0.060 (10)0.012 (10)0.039 (10)

Geometric parameters (Å, °)

Cd1—O12.301 (3)C9—C101.381 (7)
Cd1—N22.349 (3)C9—H90.9300
Cd1—N32.362 (3)C10—C111.380 (8)
Cd1—N12.363 (3)C10—H100.9300
Cd1—Cl12.5058 (11)C11—C121.384 (7)
Cd1—Cl1i2.7520 (12)C11—H110.9300
Cl1—Cd1i2.7520 (11)C12—H120.9300
N1—C151.331 (6)C15—C161.378 (7)
N1—C191.345 (5)C15—H150.9300
N2—C201.336 (5)C16—C171.372 (8)
N2—C241.345 (5)C16—H160.9300
N3—C251.342 (5)C17—C181.379 (8)
N3—C291.347 (6)C17—H170.9300
O1—C131.247 (5)C18—C191.394 (6)
O2—C131.266 (5)C18—H180.9300
O3—C141.312 (6)C19—C201.484 (6)
O3—H3A0.8200C20—C211.398 (6)
O4—C141.204 (6)C21—C221.367 (7)
C1—C21.387 (6)C21—H210.9300
C1—C61.405 (6)C22—C231.372 (7)
C1—C131.521 (6)C22—H220.9300
C2—C31.369 (6)C23—C241.405 (6)
C2—H20.9300C23—H230.9300
C3—C41.377 (7)C24—C251.496 (6)
C3—H30.9300C25—C261.394 (6)
C4—C51.374 (7)C26—C271.371 (7)
C4—H40.9300C26—H260.9300
C5—C61.403 (6)C27—C281.379 (8)
C5—H50.9300C27—H270.9300
C6—C71.502 (6)C28—C291.383 (7)
C7—C121.399 (6)C28—H280.9300
C7—C81.405 (6)C29—H290.9300
C8—C91.380 (6)O1W—H1WA0.8500
C8—C141.512 (6)O1W—H1WB0.8500
O1—Cd1—N291.38 (11)C10—C11—H11119.8
O1—Cd1—N388.97 (11)C12—C11—H11119.8
N2—Cd1—N369.18 (12)C11—C12—C7120.9 (5)
O1—Cd1—N194.88 (12)C11—C12—H12119.5
N2—Cd1—N169.08 (12)C7—C12—H12119.5
N3—Cd1—N1138.15 (12)O1—C13—O2124.4 (4)
O1—Cd1—Cl196.17 (8)O1—C13—C1117.7 (4)
N2—Cd1—Cl1166.28 (9)O2—C13—C1117.7 (4)
N3—Cd1—Cl199.44 (9)O4—C14—O3121.6 (5)
N1—Cd1—Cl1121.40 (9)O4—C14—C8121.8 (5)
O1—Cd1—Cl1i179.22 (8)O3—C14—C8116.6 (4)
N2—Cd1—Cl1i87.87 (8)N1—C15—C16123.5 (5)
N3—Cd1—Cl1i90.99 (8)N1—C15—H15118.2
N1—Cd1—Cl1i84.62 (9)C16—C15—H15118.2
Cl1—Cd1—Cl1i84.61 (3)C17—C16—C15117.8 (5)
Cd1—Cl1—Cd1i95.39 (3)C17—C16—H16121.1
C15—N1—C19118.9 (4)C15—C16—H16121.1
C15—N1—Cd1122.7 (3)C16—C17—C18119.7 (5)
C19—N1—Cd1118.4 (3)C16—C17—H17120.1
C20—N2—C24120.8 (3)C18—C17—H17120.1
C20—N2—Cd1119.6 (3)C17—C18—C19119.3 (5)
C24—N2—Cd1119.4 (3)C17—C18—H18120.3
C25—N3—C29118.3 (4)C19—C18—H18120.3
C25—N3—Cd1119.3 (3)N1—C19—C18120.7 (4)
C29—N3—Cd1122.4 (3)N1—C19—C20116.6 (3)
C13—O1—Cd1115.1 (3)C18—C19—C20122.7 (4)
C14—O3—H3A109.5N2—C20—C21120.8 (4)
C2—C1—C6119.7 (4)N2—C20—C19115.9 (3)
C2—C1—C13117.9 (4)C21—C20—C19123.3 (4)
C6—C1—C13122.2 (4)C22—C21—C20118.4 (4)
C3—C2—C1121.2 (4)C22—C21—H21120.8
C3—C2—H2119.4C20—C21—H21120.8
C1—C2—H2119.4C21—C22—C23121.5 (4)
C2—C3—C4120.1 (5)C21—C22—H22119.3
C2—C3—H3120.0C23—C22—H22119.3
C4—C3—H3120.0C22—C23—C24117.7 (4)
C5—C4—C3119.6 (4)C22—C23—H23121.2
C5—C4—H4120.2C24—C23—H23121.2
C3—C4—H4120.2N2—C24—C23120.8 (4)
C4—C5—C6121.8 (4)N2—C24—C25116.1 (3)
C4—C5—H5119.1C23—C24—C25123.1 (4)
C6—C5—H5119.1N3—C25—C26121.9 (4)
C5—C6—C1117.5 (4)N3—C25—C24115.8 (4)
C5—C6—C7117.3 (4)C26—C25—C24122.3 (4)
C1—C6—C7125.1 (4)C27—C26—C25118.9 (5)
C12—C7—C8117.8 (4)C27—C26—H26120.6
C12—C7—C6118.3 (4)C25—C26—H26120.6
C8—C7—C6123.5 (4)C26—C27—C28120.0 (5)
C9—C8—C7120.5 (4)C26—C27—H27120.0
C9—C8—C14117.7 (4)C28—C27—H27120.0
C7—C8—C14121.8 (4)C27—C28—C29118.1 (5)
C8—C9—C10120.9 (5)C27—C28—H28120.9
C8—C9—H9119.5C29—C28—H28120.9
C10—C9—H9119.5N3—C29—C28122.9 (5)
C11—C10—C9119.3 (5)N3—C29—H29118.6
C11—C10—H10120.4C28—C29—H29118.6
C9—C10—H10120.4H1WA—O1W—H1WB109.5
C10—C11—C12120.5 (5)
O1—Cd1—Cl1—Cd1i−179.90 (8)C8—C9—C10—C11−1.5 (8)
N2—Cd1—Cl1—Cd1i57.1 (3)C9—C10—C11—C12−0.7 (8)
N3—Cd1—Cl1—Cd1i90.11 (9)C10—C11—C12—C71.6 (8)
N1—Cd1—Cl1—Cd1i−80.34 (10)C8—C7—C12—C11−0.4 (7)
Cl1i—Cd1—Cl1—Cd1i0.0C6—C7—C12—C11−172.7 (4)
O1—Cd1—N1—C1594.5 (4)Cd1—O1—C13—O2−1.7 (5)
N2—Cd1—N1—C15−175.9 (4)Cd1—O1—C13—C1175.0 (3)
N3—Cd1—N1—C15−171.6 (3)C2—C1—C13—O1−39.5 (5)
Cl1—Cd1—N1—C15−5.8 (4)C6—C1—C13—O1144.7 (4)
Cl1i—Cd1—N1—C15−86.1 (3)C2—C1—C13—O2137.4 (4)
O1—Cd1—N1—C19−85.5 (3)C6—C1—C13—O2−38.4 (5)
N2—Cd1—N1—C194.1 (3)C9—C8—C14—O4−45.6 (6)
N3—Cd1—N1—C198.5 (4)C7—C8—C14—O4135.2 (5)
Cl1—Cd1—N1—C19174.3 (2)C9—C8—C14—O3132.2 (4)
Cl1i—Cd1—N1—C1993.9 (3)C7—C8—C14—O3−47.1 (6)
O1—Cd1—N2—C2089.0 (3)C19—N1—C15—C160.7 (7)
N3—Cd1—N2—C20177.4 (3)Cd1—N1—C15—C16−179.2 (4)
N1—Cd1—N2—C20−5.7 (3)N1—C15—C16—C171.0 (8)
Cl1—Cd1—N2—C20−147.5 (3)C15—C16—C17—C18−1.4 (8)
Cl1i—Cd1—N2—C20−90.7 (3)C16—C17—C18—C190.2 (8)
O1—Cd1—N2—C24−85.8 (3)C15—N1—C19—C18−2.1 (6)
N3—Cd1—N2—C242.6 (3)Cd1—N1—C19—C18177.9 (3)
N1—Cd1—N2—C24179.5 (3)C15—N1—C19—C20177.5 (4)
Cl1—Cd1—N2—C2437.7 (5)Cd1—N1—C19—C20−2.6 (4)
Cl1i—Cd1—N2—C2494.5 (3)C17—C18—C19—N11.6 (7)
O1—Cd1—N3—C2591.9 (3)C17—C18—C19—C20−177.9 (4)
N2—Cd1—N3—C250.1 (3)C24—N2—C20—C21−0.1 (6)
N1—Cd1—N3—C25−4.2 (4)Cd1—N2—C20—C21−174.8 (3)
Cl1—Cd1—N3—C25−172.0 (3)C24—N2—C20—C19−178.8 (3)
Cl1i—Cd1—N3—C25−87.3 (3)Cd1—N2—C20—C196.4 (4)
O1—Cd1—N3—C29−88.3 (3)N1—C19—C20—N2−2.5 (5)
N2—Cd1—N3—C29179.9 (4)C18—C19—C20—N2177.0 (4)
N1—Cd1—N3—C29175.6 (3)N1—C19—C20—C21178.8 (4)
Cl1—Cd1—N3—C297.8 (3)C18—C19—C20—C21−1.7 (6)
Cl1i—Cd1—N3—C2992.5 (3)N2—C20—C21—C221.2 (6)
N2—Cd1—O1—C13−123.7 (3)C19—C20—C21—C22179.8 (4)
N3—Cd1—O1—C13167.1 (3)C20—C21—C22—C23−1.5 (7)
N1—Cd1—O1—C13−54.6 (3)C21—C22—C23—C240.8 (7)
Cl1—Cd1—O1—C1367.8 (3)C20—N2—C24—C23−0.7 (6)
C6—C1—C2—C33.2 (6)Cd1—N2—C24—C23174.1 (3)
C13—C1—C2—C3−172.7 (4)C20—N2—C24—C25−179.4 (3)
C1—C2—C3—C4−1.9 (7)Cd1—N2—C24—C25−4.7 (4)
C2—C3—C4—C5−1.1 (7)C22—C23—C24—N20.4 (6)
C3—C4—C5—C62.8 (7)C22—C23—C24—C25179.0 (4)
C4—C5—C6—C1−1.4 (6)C29—N3—C25—C26−1.0 (6)
C4—C5—C6—C7−177.8 (4)Cd1—N3—C25—C26178.8 (3)
C2—C1—C6—C5−1.6 (6)C29—N3—C25—C24177.8 (4)
C13—C1—C6—C5174.2 (4)Cd1—N3—C25—C24−2.3 (4)
C2—C1—C6—C7174.5 (4)N2—C24—C25—N34.6 (5)
C13—C1—C6—C7−9.7 (6)C23—C24—C25—N3−174.2 (4)
C5—C6—C7—C1285.8 (5)N2—C24—C25—C26−176.6 (4)
C1—C6—C7—C12−90.3 (5)C23—C24—C25—C264.7 (6)
C5—C6—C7—C8−86.0 (5)N3—C25—C26—C270.5 (7)
C1—C6—C7—C897.9 (5)C24—C25—C26—C27−178.2 (4)
C12—C7—C8—C9−1.7 (6)C25—C26—C27—C28−0.2 (8)
C6—C7—C8—C9170.2 (4)C26—C27—C28—C290.5 (8)
C12—C7—C8—C14177.5 (4)C25—N3—C29—C281.2 (7)
C6—C7—C8—C14−10.6 (6)Cd1—N3—C29—C28−178.6 (4)
C7—C8—C9—C102.7 (7)C27—C28—C29—N3−1.0 (8)
C14—C8—C9—C10−176.6 (4)

Symmetry codes: (i) −x+2, −y+2, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3A···O20.821.682.487 (4)169
O1W—H1WA···O4ii0.852.412.862 (14)114
O1W—H1WB···O4iii0.852.363.093 (16)145
C16—H16···O4iv0.932.433.284 (6)153
C21—H21···O3v0.932.493.405 (6)169
C26—H26···Cl1iii0.932.753.579 (5)149

Symmetry codes: (ii) −x+2, −y+1, −z+2; (iii) x−1, y, z; (iv) −x+3, −y+2, −z+2; (v) −x+2, −y+2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NK2006).

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