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Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 64| Part 7| July 2008| Pages m851-m852

Bis(5-chloro­salicylato-κO)bis­­(1,10-phenanthroline-κ2N,N′)cadmium(II)

aDepartment of Chemistry, Longyan University, Longyan, Fujian 364000, People's Republic of China
*Correspondence e-mail: wendecai1227@yahoo.com.cn

(Received 7 May 2008; accepted 25 May 2008; online 7 June 2008)

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 ππ 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[Lemoine, P., Viossat, B., Dung, N. H., Tomas, A., Morgant, G., Greenaway, F. T. & Sorenson, J. R. J. (2004). J. Inorg. Biochem. 98, 1734-1749.]); Melnik et al. (2001[Melnik, M., Koman, M., Moncol, J. & Glowiak, T. (2001). J. Coord. Chem. 53, 173-177.]); Wen, Liu & Ribas (2007[Wen, D.-C., Liu, S.-X. & Ribas, J. (2007). Polyhedron, 26, 3849-3856.]); Wen & Ying (2007[Wen, D. & Ying, S. (2007). Acta Cryst. E63, m2407-m2408.]); Wen, Ta et al. (2007[Wen, D., Ta, H., Zhong, C., Xie, T. & Wu, L. (2007). Acta Cryst. E63, m2446-m2447.]); Yin et al. (2004[Yin, M.-C., Yuan, L.-J., Ai, C.-C., Wang, C.-W., Yuan, E.-T. & Sun, J.-T. (2004). Polyhedron, 23, 529-536.]); Zhu et al. (2003[Zhu, L.-G., Kitagawa, S., Miyasaka, H. & Chang, H.-C. (2003). Inorg. Chim. Acta, 355, 121-126.]).

[Scheme 1]

Experimental

Crystal data
  • [Cd(C7H4ClO3)2(C12H8N2)2]

  • Mr = 815.91

  • Orthorhombic, P 21 21 21

  • 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)

  • Rint = 0.086

Refinement
  • R[F2 > 2σ(F2)] = 0.045

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), with 3402 Friedel pairs

  • Flack parameter: 0.00 (19)

Table 1
Selected geometric parameters (Å, °)

Cd1—O4 2.261 (3)
Cd1—O1 2.336 (4)
Cd1—N4 2.400 (3)
Cd1—N2 2.400 (4)
Cd1—N1 2.422 (3)
Cd1—N3 2.423 (3)
O4—Cd1—O1 82.14 (12)
O4—Cd1—N4 125.46 (12)
O1—Cd1—N4 83.28 (13)
O4—Cd1—N2 86.00 (13)
O1—Cd1—N2 156.59 (12)
N4—Cd1—N2 87.33 (12)
O4—Cd1—N1 84.29 (12)
O1—Cd1—N1 129.12 (13)
N4—Cd1—N1 141.39 (12)
N2—Cd1—N1 69.12 (12)
O4—Cd1—N3 164.68 (11)
O1—Cd1—N3 97.76 (14)
N4—Cd1—N3 69.51 (11)
N2—Cd1—N3 98.95 (13)
N1—Cd1—N3 83.98 (12)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H3⋯O2 0.82 1.76 2.504 (6) 149
O6—H6⋯O5 0.82 1.83 2.553 (6) 147
C15—H15A⋯O2 0.93 2.45 3.181 (6) 136
C36—H36A⋯O5 0.93 2.34 3.134 (6) 143
C24—H24A⋯O3i 0.93 2.42 3.185 (6) 140
Symmetry code: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL-Plus (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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 ππ 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).

Related literature top

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

Experimental top

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 top

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).

Computing details top

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

Figures top
[Figure 1] Fig. 1. Molecular structure of the title complex with displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A packing view of the title complex, showing the O—H···O and C—H···O hydrogen bonds and the ππ interactions as dashed lines.
Bis(5-chlorosalicylato-κO)bis(1,10-phenanthroline-κ2N,N')cadmium(II) top
Crystal data top
[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 = 3.1–27.5°
b = 16.495 (4) ŵ = 0.86 mm1
c = 18.862 (5) ÅT = 293 K
V = 3363.9 (14) Å3Block, colourless
Z = 40.25 × 0.23 × 0.22 mm
F(000) = 1640
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
5812 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.086
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω scansh = 1214
32955 measured reflectionsk = 2121
7696 independent reflectionsl = 2424
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0296P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
7696 reflectionsΔρmax = 0.64 e Å3
461 parametersΔρmin = 0.55 e Å3
0 restraintsAbsolute structure: Flack (1983), with 3402 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (19)
Crystal data top
[Cd(C7H4ClO3)2(C12H8N2)2]V = 3363.9 (14) Å3
Mr = 815.91Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 10.812 (3) ŵ = 0.86 mm1
b = 16.495 (4) ÅT = 293 K
c = 18.862 (5) Å0.25 × 0.23 × 0.22 mm
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
5812 reflections with I > 2σ(I)
32955 measured reflectionsRint = 0.086
7696 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.086Δρmax = 0.64 e Å3
S = 1.01Δρmin = 0.55 e Å3
7696 reflectionsAbsolute structure: Flack (1983), with 3402 Friedel pairs
461 parametersAbsolute structure parameter: 0.00 (19)
0 restraints
Special details top

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) top
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)
H10A0.00110.72970.61650.069*
C110.0181 (5)0.6095 (3)0.6050 (3)0.0580 (15)
H11A0.09760.61040.58630.070*
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)
Cl20.02954 (12)0.44667 (9)0.58967 (9)0.0661 (4)
Atomic displacement parameters (Å2) top
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, º) top
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—C1588.3 (4)C14—C8—C13—C12177.4 (5)
O1—Cd1—N1—C1513.3 (4)Cd1—O4—C14—O54.5 (7)
N4—Cd1—N1—C15127.7 (4)Cd1—O4—C14—C8175.4 (4)
N2—Cd1—N1—C15176.2 (4)C13—C8—C14—O44.4 (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—O52.0 (8)
N4—Cd1—N1—C2650.3 (4)C26—N1—C15—C160.0 (7)
N2—Cd1—N1—C265.8 (3)Cd1—N1—C15—C16177.9 (4)
N3—Cd1—N1—C2696.1 (3)N1—C15—C16—C171.1 (8)
O4—Cd1—N2—C2492.3 (4)C15—C16—C17—C180.5 (8)
O1—Cd1—N2—C2432.7 (6)C16—C17—C18—C261.2 (8)
N4—Cd1—N2—C2433.6 (4)C16—C17—C18—C19177.6 (5)
N1—Cd1—N2—C24177.7 (4)C17—C18—C19—C20178.6 (5)
N3—Cd1—N2—C24102.3 (4)C26—C18—C19—C202.6 (8)
O4—Cd1—N2—C2592.4 (3)C18—C19—C20—C211.9 (8)
O1—Cd1—N2—C25152.0 (3)C19—C20—C21—C254.6 (7)
N4—Cd1—N2—C25141.8 (3)C19—C20—C21—C22175.9 (5)
N1—Cd1—N2—C257.0 (3)C25—C21—C22—C231.0 (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—C230.9 (7)
N4—Cd1—N3—C27176.3 (5)Cd1—N2—C24—C23174.3 (4)
N2—Cd1—N3—C2799.9 (4)C22—C23—C24—N21.1 (8)
N1—Cd1—N3—C2732.2 (4)C24—N2—C25—C212.0 (6)
O4—Cd1—N3—C38168.0 (4)Cd1—N2—C25—C21173.6 (3)
O1—Cd1—N3—C3879.4 (3)C24—N2—C25—C26176.7 (4)
N4—Cd1—N3—C380.4 (3)Cd1—N2—C25—C267.7 (5)
N2—Cd1—N3—C3884.1 (3)C22—C21—C25—N21.1 (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—C3675.4 (4)C20—C21—C25—C262.8 (7)
N2—Cd1—N4—C3683.1 (4)C15—N1—C26—C181.9 (6)
N1—Cd1—N4—C36134.1 (4)Cd1—N1—C26—C18176.3 (3)
N3—Cd1—N4—C36176.3 (4)C15—N1—C26—C25177.5 (4)
O4—Cd1—N4—C37175.3 (3)Cd1—N1—C26—C254.4 (5)
O1—Cd1—N4—C3799.9 (3)C17—C18—C26—N12.4 (7)
N2—Cd1—N4—C37101.6 (3)C19—C18—C26—N1176.4 (4)
N1—Cd1—N4—C3750.6 (4)C17—C18—C26—C25176.9 (4)
N3—Cd1—N4—C371.0 (3)C19—C18—C26—C254.3 (6)
O4—Cd1—O1—C775.3 (3)N2—C25—C26—N12.1 (6)
N4—Cd1—O1—C7157.4 (4)C21—C25—C26—N1179.1 (4)
N2—Cd1—O1—C7135.6 (4)N2—C25—C26—C18177.2 (4)
N1—Cd1—O1—C70.7 (4)C21—C25—C26—C181.5 (6)
N3—Cd1—O1—C789.2 (3)C38—N3—C27—C281.5 (8)
O1—Cd1—O4—C1483.4 (4)Cd1—N3—C27—C28177.3 (4)
N4—Cd1—O4—C147.4 (4)N3—C27—C28—C290.4 (9)
N2—Cd1—O4—C1476.4 (4)C27—C28—C29—C301.9 (9)
N1—Cd1—O4—C14145.8 (4)C28—C29—C30—C381.6 (9)
N3—Cd1—O4—C14174.0 (5)C28—C29—C30—C31177.7 (6)
C6—C1—C2—O3176.7 (5)C29—C30—C31—C32174.7 (6)
C7—C1—C2—O37.7 (8)C38—C30—C31—C324.6 (9)
C6—C1—C2—C30.4 (8)C30—C31—C32—C332.8 (9)
C7—C1—C2—C3175.2 (5)C31—C32—C33—C371.7 (8)
O3—C2—C3—C4176.6 (6)C31—C32—C33—C34179.7 (6)
C1—C2—C3—C40.5 (10)C37—C33—C34—C350.6 (8)
C2—C3—C4—C50.4 (9)C32—C33—C34—C35179.3 (6)
C3—C4—C5—C61.4 (9)C33—C34—C35—C360.7 (9)
C3—C4—C5—Cl1179.2 (5)C37—N4—C36—C350.7 (8)
C4—C5—C6—C11.4 (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—C33174.9 (4)
Cd1—O1—C7—O222.3 (7)C36—N4—C37—C38177.1 (5)
Cd1—O1—C7—C1155.3 (4)Cd1—N4—C37—C381.5 (6)
C6—C1—C7—O2179.1 (5)C34—C33—C37—N40.6 (7)
C2—C1—C7—O25.4 (8)C32—C33—C37—N4179.3 (5)
C6—C1—C7—O13.2 (7)C34—C33—C37—C38177.0 (5)
C2—C1—C7—O1172.4 (5)C32—C33—C37—C384.3 (7)
C13—C8—C9—O6178.5 (5)C27—N3—C38—C301.8 (7)
C14—C8—C9—O61.0 (8)Cd1—N3—C38—C30178.0 (4)
C13—C8—C9—C100.2 (8)C27—N3—C38—C37176.0 (4)
C14—C8—C9—C10177.3 (5)Cd1—N3—C38—C370.2 (5)
O6—C9—C10—C11178.4 (6)C29—C30—C38—N30.2 (8)
C8—C9—C10—C110.1 (9)C31—C30—C38—N3179.6 (5)
C9—C10—C11—C120.1 (10)C29—C30—C38—C37177.5 (5)
C10—C11—C12—C130.2 (9)C31—C30—C38—C371.8 (7)
C10—C11—C12—Cl2178.2 (5)N4—C37—C38—N31.2 (7)
C11—C12—C13—C80.0 (8)C33—C37—C38—N3175.4 (4)
Cl2—C12—C13—C8178.1 (4)N4—C37—C38—C30179.0 (5)
C9—C8—C13—C120.2 (7)C33—C37—C38—C302.5 (7)
Hydrogen-bond geometry (Å, º) top
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 code: (i) x+1, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formula[Cd(C7H4ClO3)2(C12H8N2)2]
Mr815.91
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)10.812 (3), 16.495 (4), 18.862 (5)
V3)3363.9 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.86
Crystal size (mm)0.25 × 0.23 × 0.22
Data collection
DiffractometerRigaku R-AXIS RAPID IP
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
32955, 7696, 5812
Rint0.086
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.086, 1.01
No. of reflections7696
No. of parameters461
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.64, 0.55
Absolute structureFlack (1983), with 3402 Friedel pairs
Absolute structure parameter0.00 (19)

Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Selected geometric parameters (Å, º) top
Cd1—O42.261 (3)Cd1—N22.400 (4)
Cd1—O12.336 (4)Cd1—N12.422 (3)
Cd1—N42.400 (3)Cd1—N32.423 (3)
O4—Cd1—O182.14 (12)N4—Cd1—N1141.39 (12)
O4—Cd1—N4125.46 (12)N2—Cd1—N169.12 (12)
O1—Cd1—N483.28 (13)O4—Cd1—N3164.68 (11)
O4—Cd1—N286.00 (13)O1—Cd1—N397.76 (14)
O1—Cd1—N2156.59 (12)N4—Cd1—N369.51 (11)
N4—Cd1—N287.33 (12)N2—Cd1—N398.95 (13)
O4—Cd1—N184.29 (12)N1—Cd1—N383.98 (12)
O1—Cd1—N1129.12 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O20.821.762.504 (6)149.2
O6—H6···O50.821.832.553 (6)146.7
C15—H15A···O20.932.453.181 (6)135.7
C36—H36A···O50.932.343.134 (6)143.4
C24—H24A···O3i0.932.423.185 (6)139.8
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

Acknowledgements

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

References

First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationLemoine, P., Viossat, B., Dung, N. H., Tomas, A., Morgant, G., Greenaway, F. T. & Sorenson, J. R. J. (2004). J. Inorg. Biochem. 98, 1734–1749.  Web of Science CSD CrossRef PubMed CAS Google Scholar
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First citationWen, D. & Ying, S. (2007). Acta Cryst. E63, m2407–m2408.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationYin, M.-C., Yuan, L.-J., Ai, C.-C., Wang, C.-W., Yuan, E.-T. & Sun, J.-T. (2004). Polyhedron, 23, 529–536.  Web of Science CSD CrossRef CAS Google Scholar
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Volume 64| Part 7| July 2008| Pages m851-m852
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