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Acta Crystallogr Sect E Struct Rep Online. 2008 July 1; 64(Pt 7): m851–m852.
Published online 2008 June 7. doi:  10.1107/S1600536808015687
PMCID: PMC2961793

Bis(5-chloro­salicylato-κO)bis­(1,10-phenanthroline-κ2 N,N′)cadmium(II)

Abstract

In the title complex, [Cd(C7H4ClO3)2(C12H8N2)2], the Cd atom is coordinated by two 5-chloro­salicylate ligands and two 1,10-phenanthroline ligands, displaying a distorted octa­hedral coordination geometry. The crystal structure is stabilized by O—H(...)O and C—H(...)O hydrogen bonds and π–π inter­actions between the 1,10-phenanthroline ligands and 5-chloro­salicylate ligands, with a centroid–centroid distance between neighbouring aromatic rings of 3.730 (1) Å.

Related literature

For related literature, see: Lemoine et al. (2004 [triangle]); Melnik et al. (2001 [triangle]); Wen, Liu & Ribas (2007 [triangle]); Wen & Ying (2007 [triangle]); Wen, Ta et al. (2007 [triangle]); Yin et al. (2004 [triangle]); Zhu et al. (2003 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0m851-scheme1.jpg

Experimental

Crystal data

  • [Cd(C7H4ClO3)2(C12H8N2)2]
  • M r = 815.91
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m851-efi1.jpg
  • a = 10.812 (3) Å
  • b = 16.495 (4) Å
  • c = 18.862 (5) Å
  • V = 3363.9 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.86 mm−1
  • T = 293 (2) K
  • 0.25 × 0.23 × 0.22 mm

Data collection

  • Rigaku R-AXIS RAPID IP diffractometer
  • Absorption correction: none
  • 32955 measured reflections
  • 7696 independent reflections
  • 5812 reflections with I > 2σ(I)
  • R int = 0.086

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.086
  • S = 1.01
  • 7696 reflections
  • 461 parameters
  • H-atom parameters constrained
  • Δρmax = 0.64 e Å−3
  • Δρmin = −0.55 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 3402 Friedel pairs
  • Flack parameter: 0.00 (19)

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Selected geometric parameters (Å, °)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015687/wn2261sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015687/wn2261Isup2.hkl

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

Acknowledgments

This work was supported financially by the Education Department of Fujian Province (grant No. JA02261) and Longyan Science and Technology Bureau (grant No. 2003LY03).

supplementary crystallographic information

Comment

Salicylic acid and its derivatives continue to attract attention because of their versatile coordination modes (Zhu et al., 2003; Yin et al., 2004; Wen, Liu & Ribas, 2007) and biological applications (Lemoine et al., 2004). We report here the structure of a Cd (II) complex with the 5-chlorosalicylate ligand (Melnik et al., 2001; Wen & Ying, 2007; Wen, Ta et al., 2007). The title complex, Cd(C7H4ClO3)2 (C12H8N2)2, was synthesized under hydrothermal conditions.

The Cd atom is coordinated in a distorted octahedral coordination geometry by two O atoms from two 5-chlorosalicylate ligands and four N atoms from two 1,10-phenanthroline ligands (Fig. 1 and Table 1). The crystal structure is stabilized by O—H···O and C—H···O hydrogen bonds (Table 2), and π–π interactions between the 1,10-phenanthroline ligands and 5-chlorosalicylate ligands, with a centroid–centroid distance between neighbouring aromatic rings of 3.730 (1) Å (Fig. 2).

Experimental

A mixture of Cd(NO3)2.6H2O (0.1 mmol), 1,10-phenanthroline (0.1 mmol), 5-chlorosalicylic acid (0.2 mmol) and distilled water (10 ml) was put into a Teflon-lined autoclave (20 ml) and then heated at 130 °C for 48 h. Colorless, block-like crystals of the title compound suitable for X-ray analysis were collected from the reaction mixture.

Refinement

H atoms on C atoms were positioned geometrically and refined as riding, with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). H atoms of hydroxyl groups were found in a difference Fourier map; they were then placed in calculated positions and refined as riding, with O—H = 0.82 Å and Uiso(H) = 1.2Ueq(O).

Figures

Fig. 1.
Molecular structure of the title complex with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.
Fig. 2.
A packing view of the title complex, showing the O—H···O and C—H···O hydrogen bonds and the π–π interactions as dashed lines.

Crystal data

[Cd(C7H4ClO3)2(C12H8N2)2]Dx = 1.611 Mg m3
Mr = 815.91Mo Kα radiation λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 7696 reflections
a = 10.812 (3) Åθ = 3.1–27.5º
b = 16.495 (4) ŵ = 0.86 mm1
c = 18.862 (5) ÅT = 293 (2) K
V = 3363.9 (14) Å3Block, colourless
Z = 40.25 × 0.23 × 0.22 mm
F000 = 1640

Data collection

Rigaku R-AXIS RAPID IP diffractometer5812 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.086
Monochromator: graphiteθmax = 27.5º
T = 293(2) Kθmin = 3.1º
ω scansh = −12→14
Absorption correction: nonek = −21→21
32955 measured reflectionsl = −24→24
7696 independent reflections

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045  w = 1/[σ2(Fo2) + (0.0296P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.086(Δ/σ)max = 0.001
S = 1.01Δρmax = 0.64 e Å3
7696 reflectionsΔρmin = −0.55 e Å3
461 parametersExtinction correction: none
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 3402 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.00 (19)

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*/Ueq
Cd10.59780 (3)0.543762 (17)0.728736 (18)0.03400 (8)
N10.6215 (3)0.42023 (19)0.6606 (2)0.0351 (8)
N20.6379 (3)0.57366 (19)0.6064 (2)0.0405 (9)
N30.8074 (3)0.51532 (19)0.7668 (2)0.0376 (8)
N40.7042 (3)0.66724 (19)0.7571 (2)0.0386 (9)
O10.5104 (3)0.5619 (2)0.8409 (2)0.0605 (10)
O20.5242 (4)0.4294 (3)0.8289 (2)0.0812 (13)
O30.3784 (5)0.3371 (2)0.8932 (3)0.1014 (17)
H30.43800.35120.86930.122*
O40.3969 (3)0.5341 (2)0.69660 (18)0.0548 (8)
O50.4036 (4)0.6686 (2)0.6992 (2)0.0669 (10)
O60.2125 (4)0.7513 (2)0.6663 (2)0.0731 (12)
H60.28420.74340.67860.088*
C10.3742 (4)0.4805 (2)0.9087 (3)0.0388 (11)
C20.3237 (6)0.4034 (3)0.9218 (3)0.0581 (15)
C30.2220 (6)0.3961 (4)0.9663 (4)0.0672 (17)
H3A0.18830.34510.97470.081*
C40.1713 (5)0.4616 (4)0.9977 (3)0.0624 (15)
H4A0.10290.45601.02720.075*
C50.2221 (4)0.5366 (3)0.9854 (3)0.0528 (13)
C60.3213 (4)0.5468 (3)0.9411 (3)0.0452 (11)
H6A0.35280.59840.93290.054*
C70.4778 (5)0.4913 (4)0.8564 (3)0.0526 (13)
C80.2189 (4)0.6063 (3)0.6605 (3)0.0405 (11)
C90.1585 (5)0.6802 (3)0.6510 (3)0.0493 (13)
C100.0397 (5)0.6807 (3)0.6231 (3)0.0572 (16)
H10A−0.00110.72970.61650.069*
C11−0.0181 (5)0.6095 (3)0.6050 (3)0.0580 (15)
H11A−0.09760.61040.58630.070*
C120.0422 (4)0.5369 (3)0.6149 (3)0.0473 (12)
C130.1593 (4)0.5347 (3)0.6422 (3)0.0397 (11)
H13A0.19910.48520.64850.048*
C140.3497 (4)0.6014 (3)0.6875 (3)0.0484 (12)
C150.6077 (5)0.3456 (2)0.6847 (3)0.0438 (11)
H15A0.58410.33910.73180.053*
C160.6260 (5)0.2764 (3)0.6442 (3)0.0531 (14)
H16A0.61360.22520.66350.064*
C170.6625 (5)0.2852 (3)0.5757 (3)0.0556 (14)
H17A0.67600.23970.54760.067*
C180.6800 (4)0.3631 (3)0.5471 (3)0.0443 (12)
C190.7225 (5)0.3769 (3)0.4766 (3)0.0563 (14)
H19A0.74150.33270.44800.068*
C200.7358 (5)0.4521 (4)0.4505 (3)0.0573 (13)
H20A0.76610.45950.40480.069*
C210.7036 (4)0.5214 (3)0.4930 (3)0.0448 (12)
C220.7083 (5)0.6011 (3)0.4667 (3)0.0592 (15)
H22A0.73360.61090.42030.071*
C230.6757 (6)0.6634 (3)0.5094 (3)0.0614 (16)
H23A0.67590.71640.49240.074*
C240.6420 (5)0.6471 (3)0.5792 (3)0.0499 (14)
H24A0.62120.69060.60830.060*
C250.6666 (4)0.5101 (3)0.5636 (3)0.0353 (10)
C260.6559 (4)0.4298 (2)0.5917 (3)0.0342 (10)
C270.8556 (4)0.4427 (3)0.7750 (3)0.0476 (11)
H27A0.80710.39790.76370.057*
C280.9760 (5)0.4291 (3)0.7999 (3)0.0541 (14)
H28A1.00640.37670.80520.065*
C291.0470 (5)0.4942 (3)0.8160 (3)0.0561 (14)
H29A1.12800.48680.83120.067*
C300.9987 (4)0.5725 (3)0.8097 (3)0.0442 (12)
C311.0676 (4)0.6433 (3)0.8284 (3)0.0568 (15)
H31A1.15000.63790.84160.068*
C321.0166 (5)0.7175 (3)0.8272 (3)0.0576 (15)
H32A1.06240.76230.84160.069*
C330.8916 (5)0.7276 (2)0.8039 (3)0.0449 (11)
C340.8324 (5)0.8039 (3)0.8018 (3)0.0583 (15)
H34A0.87470.85010.81640.070*
C350.7141 (4)0.8102 (3)0.7785 (4)0.0566 (14)
H35A0.67400.86010.77740.068*
C360.6538 (4)0.7391 (3)0.7561 (3)0.0498 (14)
H36A0.57300.74350.73960.060*
C370.8229 (4)0.6599 (2)0.7804 (3)0.0358 (10)
C380.8774 (4)0.5804 (2)0.7848 (2)0.0363 (10)
Cl10.15573 (18)0.61989 (11)1.02771 (12)0.1006 (7)
Cl2−0.02954 (12)0.44667 (9)0.58967 (9)0.0661 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cd10.02979 (13)0.03431 (13)0.03791 (16)−0.00051 (14)−0.00110 (16)−0.00186 (15)
N10.034 (2)0.0349 (16)0.037 (2)−0.0032 (15)0.0010 (17)−0.0025 (15)
N20.049 (2)0.0334 (17)0.039 (2)−0.0031 (16)−0.0037 (18)0.0030 (16)
N30.0365 (17)0.0416 (17)0.035 (2)−0.0004 (15)0.000 (2)−0.0025 (18)
N40.0321 (17)0.0408 (17)0.043 (3)−0.0007 (15)0.0025 (17)−0.0043 (17)
O10.053 (2)0.088 (3)0.041 (2)−0.014 (2)0.0066 (17)0.001 (2)
O20.079 (3)0.103 (3)0.061 (3)0.018 (2)0.021 (2)−0.019 (2)
O30.140 (4)0.051 (2)0.113 (4)−0.002 (3)0.036 (4)−0.015 (2)
O40.0339 (15)0.066 (2)0.065 (2)0.008 (2)−0.0101 (18)−0.0056 (18)
O50.0520 (19)0.072 (2)0.077 (3)−0.022 (2)−0.012 (2)−0.0070 (19)
O60.076 (3)0.0439 (19)0.100 (4)−0.0039 (19)−0.018 (3)−0.004 (2)
C10.038 (3)0.044 (2)0.034 (3)0.0016 (19)0.000 (2)0.0017 (19)
C20.075 (4)0.048 (3)0.051 (4)−0.001 (3)−0.002 (3)−0.001 (3)
C30.070 (4)0.060 (3)0.071 (5)−0.017 (3)0.004 (4)0.019 (3)
C40.051 (3)0.077 (4)0.060 (4)−0.001 (3)0.007 (3)0.018 (4)
C50.047 (3)0.056 (3)0.055 (3)0.013 (3)0.010 (2)0.001 (3)
C60.046 (2)0.043 (2)0.047 (3)0.000 (3)0.003 (2)0.011 (3)
C70.047 (3)0.072 (3)0.039 (3)0.001 (3)−0.005 (2)−0.006 (3)
C80.030 (2)0.048 (3)0.043 (3)−0.003 (2)−0.001 (2)−0.001 (2)
C90.049 (3)0.047 (3)0.052 (4)0.000 (2)0.001 (3)0.001 (2)
C100.051 (3)0.049 (3)0.072 (5)0.011 (3)−0.005 (3)0.010 (3)
C110.034 (3)0.069 (3)0.071 (4)0.003 (3)−0.012 (3)0.005 (3)
C120.031 (2)0.054 (3)0.056 (3)−0.007 (2)−0.003 (2)0.011 (3)
C130.031 (2)0.041 (2)0.048 (3)0.000 (2)−0.004 (2)0.009 (2)
C140.035 (2)0.066 (3)0.043 (3)−0.008 (3)0.000 (2)0.001 (3)
C150.050 (3)0.036 (2)0.046 (3)−0.001 (2)0.008 (3)0.0002 (19)
C160.065 (4)0.033 (2)0.062 (4)0.000 (2)0.008 (3)0.001 (2)
C170.064 (4)0.046 (3)0.057 (4)0.003 (3)0.008 (3)−0.007 (3)
C180.042 (3)0.047 (3)0.044 (3)−0.003 (2)−0.005 (2)−0.009 (2)
C190.063 (3)0.062 (3)0.044 (4)−0.005 (3)0.001 (3)−0.019 (3)
C200.064 (3)0.079 (3)0.029 (3)−0.006 (3)0.000 (2)−0.007 (3)
C210.048 (3)0.057 (3)0.029 (3)−0.011 (2)−0.006 (2)0.005 (2)
C220.069 (4)0.073 (4)0.035 (3)−0.019 (3)−0.008 (3)0.009 (3)
C230.083 (4)0.048 (3)0.053 (4)−0.011 (3)−0.014 (3)0.015 (3)
C240.055 (3)0.037 (2)0.057 (4)−0.001 (2)−0.005 (3)0.004 (2)
C250.029 (2)0.042 (2)0.035 (3)−0.0043 (19)−0.008 (2)−0.003 (2)
C260.029 (2)0.039 (2)0.034 (3)−0.0043 (18)−0.007 (2)0.0000 (19)
C270.051 (2)0.044 (3)0.048 (3)0.005 (2)−0.004 (3)−0.004 (3)
C280.059 (3)0.048 (3)0.055 (4)0.013 (2)−0.004 (3)0.003 (2)
C290.043 (3)0.070 (3)0.055 (4)0.009 (3)−0.012 (3)0.004 (3)
C300.034 (2)0.049 (3)0.049 (3)−0.002 (2)−0.006 (2)0.005 (2)
C310.037 (3)0.064 (3)0.070 (4)−0.002 (2)−0.021 (3)−0.001 (3)
C320.045 (3)0.058 (3)0.070 (4)−0.010 (3)−0.017 (3)0.000 (3)
C330.040 (2)0.048 (2)0.046 (3)−0.010 (2)−0.003 (3)0.002 (2)
C340.054 (3)0.044 (3)0.077 (4)−0.012 (2)−0.004 (3)−0.014 (3)
C350.053 (3)0.039 (2)0.078 (4)0.007 (2)−0.008 (3)−0.009 (3)
C360.039 (2)0.045 (2)0.066 (4)0.004 (2)−0.007 (2)−0.001 (2)
C370.034 (2)0.041 (2)0.033 (3)−0.0050 (18)0.003 (2)−0.002 (2)
C380.036 (2)0.044 (2)0.029 (3)−0.0012 (18)−0.0002 (19)0.0018 (18)
Cl10.1042 (14)0.0923 (12)0.1054 (17)0.0301 (10)0.0478 (12)0.0013 (11)
Cl20.0482 (7)0.0668 (8)0.0834 (11)−0.0173 (7)−0.0204 (7)0.0048 (8)

Geometric parameters (Å, °)

Cd1—O42.261 (3)C12—Cl21.745 (5)
Cd1—O12.336 (4)C13—H13A0.9300
Cd1—N42.400 (3)C15—C161.388 (6)
Cd1—N22.400 (4)C15—H15A0.9300
Cd1—N12.422 (3)C16—C171.360 (8)
Cd1—N32.423 (3)C16—H16A0.9300
N1—C151.320 (5)C17—C181.406 (7)
N1—C261.361 (6)C17—H17A0.9300
N2—C241.316 (5)C18—C261.410 (6)
N2—C251.359 (5)C18—C191.425 (7)
N3—C271.316 (5)C19—C201.343 (8)
N3—C381.357 (5)C19—H19A0.9300
N4—C361.304 (5)C20—C211.438 (7)
N4—C371.362 (5)C20—H20A0.9300
O1—C71.252 (6)C21—C251.403 (7)
O2—C71.250 (6)C21—C221.407 (7)
O3—C21.356 (6)C22—C231.352 (8)
O3—H30.8200C22—H22A0.9300
O4—C141.233 (6)C23—C241.393 (8)
O5—C141.272 (5)C23—H23A0.9300
O6—C91.342 (6)C24—H24A0.9300
O6—H60.8200C25—C261.433 (6)
C1—C61.377 (6)C27—C281.402 (7)
C1—C21.405 (7)C27—H27A0.9300
C1—C71.504 (7)C28—C291.355 (7)
C2—C31.389 (8)C28—H28A0.9300
C3—C41.348 (8)C29—C301.397 (6)
C3—H3A0.9300C29—H29A0.9300
C4—C51.374 (8)C30—C381.399 (6)
C4—H4A0.9300C30—C311.430 (6)
C5—C61.370 (7)C31—C321.343 (7)
C5—Cl11.743 (5)C31—H31A0.9300
C6—H6A0.9300C32—C331.430 (7)
C8—C131.390 (6)C32—H32A0.9300
C8—C91.394 (6)C33—C371.412 (6)
C8—C141.506 (6)C33—C341.414 (6)
C9—C101.388 (7)C34—C351.356 (7)
C10—C111.372 (7)C34—H34A0.9300
C10—H10A0.9300C35—C361.407 (6)
C11—C121.376 (7)C35—H35A0.9300
C11—H11A0.9300C36—H36A0.9300
C12—C131.368 (6)C37—C381.441 (6)
O4—Cd1—O182.14 (12)N1—C15—C16124.1 (5)
O4—Cd1—N4125.46 (12)N1—C15—H15A117.9
O1—Cd1—N483.28 (13)C16—C15—H15A117.9
O4—Cd1—N286.00 (13)C17—C16—C15118.5 (4)
O1—Cd1—N2156.59 (12)C17—C16—H16A120.7
N4—Cd1—N287.33 (12)C15—C16—H16A120.7
O4—Cd1—N184.29 (12)C16—C17—C18120.0 (5)
O1—Cd1—N1129.12 (13)C16—C17—H17A120.0
N4—Cd1—N1141.39 (12)C18—C17—H17A120.0
N2—Cd1—N169.12 (12)C17—C18—C26117.3 (5)
O4—Cd1—N3164.68 (11)C17—C18—C19123.1 (5)
O1—Cd1—N397.76 (14)C26—C18—C19119.5 (4)
N4—Cd1—N369.51 (11)C20—C19—C18121.6 (5)
N2—Cd1—N398.95 (13)C20—C19—H19A119.2
N1—Cd1—N383.98 (12)C18—C19—H19A119.2
C15—N1—C26117.9 (4)C19—C20—C21120.3 (5)
C15—N1—Cd1126.1 (3)C19—C20—H20A119.9
C26—N1—Cd1116.0 (3)C21—C20—H20A119.9
C24—N2—C25118.1 (4)C25—C21—C22118.0 (5)
C24—N2—Cd1124.7 (3)C25—C21—C20119.5 (4)
C25—N2—Cd1117.0 (3)C22—C21—C20122.5 (5)
C27—N3—C38118.0 (4)C23—C22—C21119.4 (5)
C27—N3—Cd1125.6 (3)C23—C22—H22A120.3
C38—N3—Cd1116.3 (2)C21—C22—H22A120.3
C36—N4—C37118.6 (4)C22—C23—C24119.0 (5)
C36—N4—Cd1124.6 (3)C22—C23—H23A120.5
C37—N4—Cd1116.7 (2)C24—C23—H23A120.5
C7—O1—Cd1101.9 (3)N2—C24—C23123.7 (5)
C2—O3—H3109.5N2—C24—H24A118.2
C14—O4—Cd1111.8 (3)C23—C24—H24A118.2
C9—O6—H6109.5N2—C25—C21121.8 (4)
C6—C1—C2118.7 (4)N2—C25—C26118.4 (4)
C6—C1—C7120.4 (4)C21—C25—C26119.8 (4)
C2—C1—C7120.8 (4)N1—C26—C18122.1 (4)
O3—C2—C3121.1 (5)N1—C26—C25118.9 (4)
O3—C2—C1119.4 (5)C18—C26—C25119.1 (5)
C3—C2—C1119.4 (5)N3—C27—C28123.6 (4)
C4—C3—C2121.3 (5)N3—C27—H27A118.2
C4—C3—H3A119.4C28—C27—H27A118.2
C2—C3—H3A119.4C29—C28—C27118.3 (4)
C3—C4—C5119.0 (5)C29—C28—H28A120.9
C3—C4—H4A120.5C27—C28—H28A120.9
C5—C4—H4A120.5C28—C29—C30120.2 (4)
C6—C5—C4121.8 (5)C28—C29—H29A119.9
C6—C5—Cl1120.3 (4)C30—C29—H29A119.9
C4—C5—Cl1117.9 (4)C29—C30—C38117.7 (4)
C5—C6—C1119.8 (5)C29—C30—C31122.7 (4)
C5—C6—H6A120.1C38—C30—C31119.6 (4)
C1—C6—H6A120.1C32—C31—C30121.8 (4)
O2—C7—O1123.4 (5)C32—C31—H31A119.1
O2—C7—C1118.3 (5)C30—C31—H31A119.1
O1—C7—C1118.3 (5)C31—C32—C33119.9 (5)
C13—C8—C9119.6 (4)C31—C32—H32A120.1
C13—C8—C14118.2 (4)C33—C32—H32A120.1
C9—C8—C14122.1 (4)C37—C33—C34117.2 (4)
O6—C9—C10118.6 (5)C37—C33—C32120.2 (4)
O6—C9—C8122.2 (5)C34—C33—C32122.7 (4)
C10—C9—C8119.2 (5)C35—C34—C33120.3 (4)
C11—C10—C9120.7 (5)C35—C34—H34A119.8
C11—C10—H10A119.6C33—C34—H34A119.8
C9—C10—H10A119.6C34—C35—C36118.1 (4)
C10—C11—C12119.7 (5)C34—C35—H35A121.0
C10—C11—H11A120.2C36—C35—H35A121.0
C12—C11—H11A120.2N4—C36—C35124.0 (4)
C13—C12—C11120.9 (5)N4—C36—H36A118.0
C13—C12—Cl2119.4 (4)C35—C36—H36A118.0
C11—C12—Cl2119.7 (4)N4—C37—C33121.8 (4)
C12—C13—C8120.0 (5)N4—C37—C38119.0 (4)
C12—C13—H13A120.0C33—C37—C38119.1 (4)
C8—C13—H13A120.0N3—C38—C30122.2 (4)
O4—C14—O5124.8 (5)N3—C38—C37118.5 (4)
O4—C14—C8119.0 (4)C30—C38—C37119.2 (4)
O5—C14—C8116.2 (5)
O4—Cd1—N1—C15−88.3 (4)C14—C8—C13—C12−177.4 (5)
O1—Cd1—N1—C15−13.3 (4)Cd1—O4—C14—O5−4.5 (7)
N4—Cd1—N1—C15127.7 (4)Cd1—O4—C14—C8175.4 (4)
N2—Cd1—N1—C15−176.2 (4)C13—C8—C14—O4−4.4 (8)
N3—Cd1—N1—C1581.8 (4)C9—C8—C14—O4178.1 (5)
O4—Cd1—N1—C2693.7 (3)C13—C8—C14—O5175.5 (5)
O1—Cd1—N1—C26168.7 (3)C9—C8—C14—O5−2.0 (8)
N4—Cd1—N1—C26−50.3 (4)C26—N1—C15—C160.0 (7)
N2—Cd1—N1—C265.8 (3)Cd1—N1—C15—C16−177.9 (4)
N3—Cd1—N1—C26−96.1 (3)N1—C15—C16—C171.1 (8)
O4—Cd1—N2—C2492.3 (4)C15—C16—C17—C18−0.5 (8)
O1—Cd1—N2—C2432.7 (6)C16—C17—C18—C26−1.2 (8)
N4—Cd1—N2—C24−33.6 (4)C16—C17—C18—C19177.6 (5)
N1—Cd1—N2—C24177.7 (4)C17—C18—C19—C20178.6 (5)
N3—Cd1—N2—C24−102.3 (4)C26—C18—C19—C20−2.6 (8)
O4—Cd1—N2—C25−92.4 (3)C18—C19—C20—C21−1.9 (8)
O1—Cd1—N2—C25−152.0 (3)C19—C20—C21—C254.6 (7)
N4—Cd1—N2—C25141.8 (3)C19—C20—C21—C22−175.9 (5)
N1—Cd1—N2—C25−7.0 (3)C25—C21—C22—C23−1.0 (7)
N3—Cd1—N2—C2573.0 (3)C20—C21—C22—C23179.5 (5)
O4—Cd1—N3—C277.9 (8)C21—C22—C23—C242.0 (8)
O1—Cd1—N3—C2796.5 (4)C25—N2—C24—C23−0.9 (7)
N4—Cd1—N3—C27176.3 (5)Cd1—N2—C24—C23174.3 (4)
N2—Cd1—N3—C27−99.9 (4)C22—C23—C24—N2−1.1 (8)
N1—Cd1—N3—C27−32.2 (4)C24—N2—C25—C212.0 (6)
O4—Cd1—N3—C38−168.0 (4)Cd1—N2—C25—C21−173.6 (3)
O1—Cd1—N3—C38−79.4 (3)C24—N2—C25—C26−176.7 (4)
N4—Cd1—N3—C380.4 (3)Cd1—N2—C25—C267.7 (5)
N2—Cd1—N3—C3884.1 (3)C22—C21—C25—N2−1.1 (7)
N1—Cd1—N3—C38151.8 (3)C20—C21—C25—N2178.5 (4)
O4—Cd1—N4—C360.0 (5)C22—C21—C25—C26177.6 (4)
O1—Cd1—N4—C36−75.4 (4)C20—C21—C25—C26−2.8 (7)
N2—Cd1—N4—C3683.1 (4)C15—N1—C26—C18−1.9 (6)
N1—Cd1—N4—C36134.1 (4)Cd1—N1—C26—C18176.3 (3)
N3—Cd1—N4—C36−176.3 (4)C15—N1—C26—C25177.5 (4)
O4—Cd1—N4—C37175.3 (3)Cd1—N1—C26—C25−4.4 (5)
O1—Cd1—N4—C3799.9 (3)C17—C18—C26—N12.4 (7)
N2—Cd1—N4—C37−101.6 (3)C19—C18—C26—N1−176.4 (4)
N1—Cd1—N4—C37−50.6 (4)C17—C18—C26—C25−176.9 (4)
N3—Cd1—N4—C37−1.0 (3)C19—C18—C26—C254.3 (6)
O4—Cd1—O1—C775.3 (3)N2—C25—C26—N1−2.1 (6)
N4—Cd1—O1—C7−157.4 (4)C21—C25—C26—N1179.1 (4)
N2—Cd1—O1—C7135.6 (4)N2—C25—C26—C18177.2 (4)
N1—Cd1—O1—C7−0.7 (4)C21—C25—C26—C18−1.5 (6)
N3—Cd1—O1—C7−89.2 (3)C38—N3—C27—C28−1.5 (8)
O1—Cd1—O4—C1483.4 (4)Cd1—N3—C27—C28−177.3 (4)
N4—Cd1—O4—C147.4 (4)N3—C27—C28—C29−0.4 (9)
N2—Cd1—O4—C14−76.4 (4)C27—C28—C29—C301.9 (9)
N1—Cd1—O4—C14−145.8 (4)C28—C29—C30—C38−1.6 (9)
N3—Cd1—O4—C14174.0 (5)C28—C29—C30—C31177.7 (6)
C6—C1—C2—O3−176.7 (5)C29—C30—C31—C32−174.7 (6)
C7—C1—C2—O37.7 (8)C38—C30—C31—C324.6 (9)
C6—C1—C2—C30.4 (8)C30—C31—C32—C33−2.8 (9)
C7—C1—C2—C3−175.2 (5)C31—C32—C33—C37−1.7 (8)
O3—C2—C3—C4176.6 (6)C31—C32—C33—C34179.7 (6)
C1—C2—C3—C4−0.5 (10)C37—C33—C34—C350.6 (8)
C2—C3—C4—C5−0.4 (9)C32—C33—C34—C35179.3 (6)
C3—C4—C5—C61.4 (9)C33—C34—C35—C36−0.7 (9)
C3—C4—C5—Cl1−179.2 (5)C37—N4—C36—C35−0.7 (8)
C4—C5—C6—C1−1.4 (8)Cd1—N4—C36—C35174.5 (4)
Cl1—C5—C6—C1179.1 (4)C34—C35—C36—N40.8 (9)
C2—C1—C6—C50.5 (7)C36—N4—C37—C330.7 (7)
C7—C1—C6—C5176.1 (5)Cd1—N4—C37—C33−174.9 (4)
Cd1—O1—C7—O222.3 (7)C36—N4—C37—C38177.1 (5)
Cd1—O1—C7—C1−155.3 (4)Cd1—N4—C37—C381.5 (6)
C6—C1—C7—O2179.1 (5)C34—C33—C37—N4−0.6 (7)
C2—C1—C7—O2−5.4 (8)C32—C33—C37—N4−179.3 (5)
C6—C1—C7—O1−3.2 (7)C34—C33—C37—C38−177.0 (5)
C2—C1—C7—O1172.4 (5)C32—C33—C37—C384.3 (7)
C13—C8—C9—O6−178.5 (5)C27—N3—C38—C301.8 (7)
C14—C8—C9—O6−1.0 (8)Cd1—N3—C38—C30178.0 (4)
C13—C8—C9—C10−0.2 (8)C27—N3—C38—C37−176.0 (4)
C14—C8—C9—C10177.3 (5)Cd1—N3—C38—C370.2 (5)
O6—C9—C10—C11178.4 (6)C29—C30—C38—N3−0.2 (8)
C8—C9—C10—C110.1 (9)C31—C30—C38—N3−179.6 (5)
C9—C10—C11—C120.1 (10)C29—C30—C38—C37177.5 (5)
C10—C11—C12—C13−0.2 (9)C31—C30—C38—C37−1.8 (7)
C10—C11—C12—Cl2−178.2 (5)N4—C37—C38—N3−1.2 (7)
C11—C12—C13—C80.0 (8)C33—C37—C38—N3175.4 (4)
Cl2—C12—C13—C8178.1 (4)N4—C37—C38—C30−179.0 (5)
C9—C8—C13—C120.2 (7)C33—C37—C38—C30−2.5 (7)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.762.504 (6)149
O6—H6···O50.821.832.553 (6)147
C15—H15A···O20.932.453.181 (6)136
C36—H36A···O50.932.343.134 (6)143
C24—H24A···O3i0.932.423.185 (6)140

Symmetry codes: (i) −x+1, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2261).

References

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  • Yin, M.-C., Yuan, L.-J., Ai, C.-C., Wang, C.-W., Yuan, E.-T. & Sun, J.-T. (2004). Polyhedron, 23, 529–536.
  • Zhu, L.-G., Kitagawa, S., Miyasaka, H. & Chang, H.-C. (2003). Inorg. Chim. Acta, 355, 121–126.

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