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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808015687/wn2261sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808015687/wn2261Isup2.hkl
Contains datablock I

CCDC reference: 696386

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.045
  • wR factor = 0.087
  • Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for Cl1 -- C5 .. 5.36 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C5 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT850_ALERT_4_C Check Flack Parameter Exact Value 0.00 and su .. 0.19
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 7696 Count of symmetry unique reflns 4306 Completeness (_total/calc) 178.73% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3390 Fraction of Friedel pairs measured 0.787 Are heavy atom types Z>Si present yes PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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.
 

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