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Acta Cryst. (2007). E63, m3023    [ doi:10.1107/S1600536807055857 ]

Bis[3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]cadmium(II) tetrahydrate

K. Zhao, X.-H. Yin, Y. Feng and J. Zhu

Abstract top

In the title compound, [Cd(C11H9ClN3O2)2]·4H2O, the CdII atom is coordinated by four N atoms and two O atoms from two picolinate ligands in a distorted octahedral geometry. In the crystal structure, molecules are linked together by intermolecular O-H...O hydrogen bonds.

Comment top

In recent years, there has been an increasing interest in the coordination chemistry due to the increased recognition of it's role in catalysis enzymatic reactions, magnetism and molecular architectures (Costamagna et al., 1992; Bhatia et al., 1981). We report here the crystal structure of a new zinc(II) complex with the ligand 6-(3-chloro- (3,5-dimethyl-1H-pyrazol-1-yl)) picolinic acid(CDPA)·(I) (Fig.1).

The title compound, (I), consists of a cadmium(II) complex cation and four uncoordinated water molecules. In the cation (Fig. 1), the Cd atom is six-coordinated by four N atoms and two O atomsfrom two CDPA ligands. The Cd(II) atom is a slightly distorted octahedral environment. The Cd–O bond lengths are 2.243 (3) and 2.266 (3) Å,The Cd—N distances range from 2.320 (3) to 2.350 (3) Å. The C1–C2 bond length is 1.533 (6) Å, being in the normal C–C ranges in cadmium carboxylate complexes. The angles around Cd(II) atom are from 68.54 (11) to 139.29 (11)°. The CDPA molecule acts as a bidentate ligand.

In the title compound, the oxygen atoms contribute to the formation of intermolecular hydrogen bonds involving water O atoms. (Table 1).

Related literature top

For related literature, see: Bhatia et al. (1981); Costamagna et al. (1992).

Experimental top

6-(3-chloro-(3,5-dimethyl-1H-pyrazol-1-yl))picolinic acid, and CdCl2. 6H2O were available commercially and were used without further purification. Equimolar 6-(3-chloro-(3,5-dimethyl-1H-pyrazol-1-yl))picolinic acid (1 mmol, 250 mg) was dissolved in anhydrous alcohol (15 ml). The mixture was stirred to give a clear solution, To this solution was added CdCl2·6H2O (0.5 mmol, 142 mg) in anhydrous alcohol (10 ml). After keeping the resulting solution in air to evaporate about half of the solvents, dark red prisms of the title compound were formed. The crystals were isolated, washed with alcohol three times and dried in a vacuum desiccator using silica gel (Yield 75%). Elemental analysis: found: C, 38.43; H, 3.92; N, 12.15; O, 18.76; calc. for C22H26CdCl2N6O8: C, 38.53; H, 3.82; N, 12.25; O, 18.66%.

Refinement top

All the H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with N—H and C—H distances of 0.90 Å and 0.96 Å, respectively. They were treated as riding atoms, with Uiso(H) = 1.2Ueq(C), Uiso(H) = 1.2Ueq(N) and Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top
[Figure 1] Fig. 1. The structure of the title compound (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme.
[Figure 2] Fig. 2. Crystal packing of (I) showing the hydrogen bonded interactions as dashed lines.
Bis[3-chloro-6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinato]cadmium(II) tetrahydrate top
Crystal data top
[Cd(C11H9ClN3O2)2]·4H2OZ = 2
Mr = 685.79F000 = 692
Triclinic, P1Dx = 1.689 Mg m−3
Hall symbol: -P 1Mo Kα radiation
λ = 0.71073 Å
a = 10.1790 (10) ÅCell parameters from 3835 reflections
b = 11.4140 (14) Åθ = 2.6–27.6º
c = 13.4240 (18) ŵ = 1.07 mm−1
α = 114.745 (3)ºT = 298 (2) K
β = 102.249 (2)ºBlock, colorless
γ = 96.4280 (10)º0.51 × 0.50 × 0.48 mm
V = 1348.3 (3) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		4645 independent reflections
Radiation source: fine-focus sealed tube3752 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.020
T = 298(2) Kθmax = 25.0º
phi and ω scansθmin = 1.7º
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→11
Tmin = 0.613, Tmax = 0.629k = −6→13
6989 measured reflectionsl = −15→13
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)] = 0.037H-atom parameters constrained
wR(F2) = 0.101  w = 1/[σ2(Fo2) + (0.0431P)2 + 1.4843P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4645 reflectionsΔρmax = 0.68 e Å−3
352 parametersΔρmin = −0.60 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Cd(C11H9ClN3O2)2]·4H2Oγ = 96.4280 (10)º
Mr = 685.79V = 1348.3 (3) Å3
Triclinic, P1Z = 2
a = 10.1790 (10) ÅMo Kα
b = 11.4140 (14) ŵ = 1.07 mm−1
c = 13.4240 (18) ÅT = 298 (2) K
α = 114.745 (3)º0.51 × 0.50 × 0.48 mm
β = 102.249 (2)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		4645 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		3752 reflections with I > 2σ(I)
Tmin = 0.613, Tmax = 0.629Rint = 0.020
6989 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.037352 parameters
wR(F2) = 0.101H-atom parameters constrained
S = 1.05Δρmax = 0.68 e Å−3
4645 reflectionsΔρmin = −0.60 e Å−3
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 > 2sigma(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
Cd10.28358 (3)0.52895 (3)0.75795 (3)0.04744 (13)
Cl10.28940 (15)0.04201 (12)0.81008 (14)0.0788 (4)
Cl2−0.05630 (14)0.92388 (12)0.82716 (12)0.0679 (4)
N10.3954 (3)0.3897 (3)0.8128 (2)0.0354 (7)
N20.5982 (3)0.5488 (3)0.8803 (3)0.0366 (7)
N30.5202 (3)0.6247 (3)0.8477 (3)0.0429 (8)
N40.1674 (3)0.6646 (3)0.6998 (3)0.0363 (7)
N50.2145 (3)0.5588 (3)0.5272 (3)0.0412 (7)
N60.2745 (3)0.4811 (3)0.5704 (3)0.0461 (8)
O10.1292 (3)0.3403 (4)0.7077 (3)0.0696 (10)
O20.0848 (4)0.1492 (4)0.7108 (5)0.1164 (18)
O30.2019 (4)0.6588 (4)0.8981 (3)0.0711 (10)
O40.1175 (5)0.8337 (4)0.9710 (3)0.0928 (13)
O50.1574 (4)0.7985 (4)0.1750 (3)0.0868 (11)
H5A0.09020.81340.20330.104*
H5B0.14190.80980.11520.104*
O60.8516 (7)0.0186 (7)0.5197 (7)0.194 (3)
H6A0.92470.05650.57550.232*
H6B0.8737−0.02570.45930.232*
O70.5992 (8)0.1002 (12)0.6502 (7)0.320 (7)
H7D0.67610.13150.70210.384*
H7E0.61270.09840.58930.384*
O80.3705 (9)0.9082 (10)0.5599 (7)0.252 (5)
H8A0.30110.93450.53630.303*
H8B0.44170.97090.58760.303*
C10.1637 (5)0.2515 (5)0.7311 (4)0.0619 (13)
C20.3166 (4)0.2746 (4)0.7924 (3)0.0411 (9)
C30.3773 (4)0.1916 (4)0.8290 (4)0.0471 (10)
C40.5165 (5)0.2285 (4)0.8846 (4)0.0583 (12)
H40.55790.17300.90910.070*
C50.5943 (4)0.3456 (4)0.9043 (4)0.0520 (11)
H50.68800.37140.94280.062*
C60.5290 (4)0.4244 (4)0.8650 (3)0.0348 (8)
C70.8520 (4)0.5611 (5)0.9700 (4)0.0592 (12)
H7A0.93790.62130.99000.089*
H7B0.85090.47620.91070.089*
H7C0.84180.55231.03620.089*
C80.7345 (4)0.6139 (4)0.9277 (3)0.0425 (9)
C90.7415 (5)0.7315 (4)0.9249 (4)0.0526 (11)
H90.82080.79750.95090.063*
C100.6079 (4)0.7357 (4)0.8756 (4)0.0479 (10)
C110.5576 (6)0.8428 (5)0.8524 (5)0.0756 (15)
H11A0.48410.80360.78210.113*
H11B0.63210.89620.84600.113*
H11C0.52430.89710.91410.113*
C120.1458 (4)0.7485 (4)0.8925 (4)0.0494 (10)
C130.1089 (4)0.7461 (4)0.7743 (3)0.0379 (8)
C140.0228 (4)0.8155 (4)0.7387 (4)0.0433 (9)
C15−0.0012 (4)0.7982 (4)0.6274 (4)0.0498 (10)
H15−0.05880.84450.60300.060*
C160.0583 (4)0.7141 (4)0.5526 (4)0.0458 (10)
H160.04110.70110.47750.055*
C170.1456 (4)0.6489 (4)0.5942 (3)0.0371 (8)
C180.1855 (6)0.5966 (7)0.3503 (5)0.0856 (18)
H18A0.23020.57460.29070.128*
H18B0.21000.69070.39780.128*
H18C0.08730.56820.31680.128*
C190.2308 (4)0.5284 (5)0.4213 (4)0.0521 (11)
C200.3009 (5)0.4300 (5)0.3984 (4)0.0618 (13)
H200.32740.38840.33220.074*
C210.3260 (4)0.4027 (4)0.4918 (4)0.0520 (11)
C220.3962 (6)0.3021 (5)0.5088 (5)0.0752 (15)
H22A0.46160.34250.58340.113*
H22B0.44340.26750.45160.113*
H22C0.32880.23130.50230.113*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.04307 (19)0.0611 (2)0.0546 (2)0.02603 (15)0.01381 (14)0.03812 (16)
Cl10.0807 (9)0.0469 (7)0.1047 (11)0.0000 (6)0.0116 (8)0.0413 (7)
Cl20.0791 (8)0.0659 (7)0.0984 (10)0.0460 (7)0.0555 (8)0.0525 (7)
N10.0331 (16)0.0381 (17)0.0355 (16)0.0099 (13)0.0052 (13)0.0188 (14)
N20.0322 (16)0.0397 (17)0.0433 (18)0.0124 (14)0.0090 (14)0.0235 (15)
N30.0434 (19)0.0458 (19)0.050 (2)0.0178 (16)0.0146 (16)0.0289 (16)
N40.0327 (16)0.0420 (17)0.0405 (18)0.0120 (14)0.0097 (14)0.0242 (14)
N50.0399 (18)0.0475 (19)0.0367 (18)0.0136 (15)0.0072 (14)0.0204 (15)
N60.050 (2)0.0453 (19)0.048 (2)0.0194 (16)0.0143 (16)0.0230 (16)
O10.0348 (16)0.094 (3)0.089 (2)0.0062 (16)−0.0037 (16)0.063 (2)
O20.059 (2)0.095 (3)0.180 (5)−0.020 (2)−0.024 (3)0.085 (3)
O30.086 (2)0.108 (3)0.0575 (19)0.066 (2)0.0353 (18)0.056 (2)
O40.154 (4)0.099 (3)0.058 (2)0.078 (3)0.054 (2)0.042 (2)
O50.092 (3)0.102 (3)0.079 (3)0.045 (2)0.029 (2)0.044 (2)
O60.153 (6)0.172 (6)0.193 (7)0.002 (5)−0.010 (5)0.061 (5)
O70.161 (7)0.516 (18)0.122 (6)−0.095 (9)0.018 (5)0.049 (8)
O80.207 (8)0.286 (11)0.192 (8)0.021 (8)0.069 (7)0.045 (8)
C10.043 (2)0.066 (3)0.074 (3)0.000 (2)0.000 (2)0.039 (3)
C20.040 (2)0.041 (2)0.039 (2)0.0070 (18)0.0069 (17)0.0176 (17)
C30.054 (3)0.037 (2)0.051 (2)0.0104 (19)0.011 (2)0.0229 (19)
C40.058 (3)0.045 (3)0.076 (3)0.016 (2)0.006 (2)0.037 (2)
C50.040 (2)0.052 (3)0.069 (3)0.012 (2)0.004 (2)0.037 (2)
C60.0330 (19)0.038 (2)0.0331 (19)0.0126 (16)0.0072 (16)0.0166 (16)
C70.035 (2)0.077 (3)0.068 (3)0.008 (2)0.004 (2)0.042 (3)
C80.039 (2)0.050 (2)0.042 (2)0.0084 (18)0.0131 (18)0.0239 (19)
C90.049 (3)0.052 (3)0.054 (3)−0.001 (2)0.014 (2)0.025 (2)
C100.056 (3)0.046 (2)0.055 (3)0.016 (2)0.023 (2)0.031 (2)
C110.086 (4)0.058 (3)0.104 (4)0.022 (3)0.031 (3)0.053 (3)
C120.048 (2)0.062 (3)0.050 (3)0.023 (2)0.022 (2)0.030 (2)
C130.035 (2)0.040 (2)0.047 (2)0.0115 (17)0.0160 (17)0.0248 (18)
C140.040 (2)0.041 (2)0.064 (3)0.0161 (18)0.024 (2)0.033 (2)
C150.042 (2)0.056 (3)0.073 (3)0.022 (2)0.016 (2)0.046 (2)
C160.043 (2)0.054 (2)0.048 (2)0.0135 (19)0.0087 (19)0.033 (2)
C170.0321 (19)0.042 (2)0.041 (2)0.0068 (16)0.0073 (16)0.0236 (17)
C180.092 (4)0.137 (5)0.063 (3)0.055 (4)0.038 (3)0.063 (4)
C190.048 (2)0.070 (3)0.040 (2)0.017 (2)0.0142 (19)0.025 (2)
C200.061 (3)0.076 (3)0.045 (3)0.025 (3)0.023 (2)0.018 (2)
C210.046 (2)0.054 (3)0.053 (3)0.018 (2)0.016 (2)0.019 (2)
C220.079 (4)0.068 (3)0.088 (4)0.043 (3)0.032 (3)0.033 (3)
Geometric parameters (Å, °) top
Cd1—O32.243 (3)C3—C41.377 (6)
Cd1—O12.266 (3)C4—C51.364 (6)
Cd1—N62.320 (3)C4—H40.9300
Cd1—N12.322 (3)C5—C61.383 (5)
Cd1—N42.331 (3)C5—H50.9300
Cd1—N32.350 (3)C7—C81.508 (6)
Cl1—C31.726 (4)C7—H7A0.9600
Cl2—C141.728 (4)C7—H7B0.9600
N1—C61.319 (4)C7—H7C0.9600
N1—C21.346 (5)C8—C91.353 (6)
N2—C81.371 (5)C9—C101.396 (6)
N2—N31.378 (4)C9—H90.9300
N2—C61.423 (5)C10—C111.498 (6)
N3—C101.323 (5)C11—H11A0.9600
N4—C171.317 (5)C11—H11B0.9600
N4—C131.348 (5)C11—H11C0.9600
N5—C191.368 (5)C12—C131.539 (6)
N5—N61.378 (4)C13—C141.385 (5)
N5—C171.419 (5)C14—C151.385 (6)
N6—C211.318 (5)C15—C161.370 (6)
O1—C11.245 (5)C15—H150.9300
O2—C11.230 (6)C16—C171.393 (5)
O3—C121.248 (5)C16—H160.9300
O4—C121.213 (5)C18—C191.498 (7)
O5—H5A0.8500C18—H18A0.9600
O5—H5B0.8501C18—H18B0.9600
O6—H6A0.8500C18—H18C0.9600
O6—H6B0.8500C19—C201.359 (6)
O7—H7D0.8500C20—C211.394 (7)
O7—H7E0.8501C20—H200.9300
O8—H8A0.8500C21—C221.489 (6)
O8—H8B0.8501C22—H22A0.9600
C1—C21.533 (6)C22—H22B0.9600
C2—C31.384 (5)C22—H22C0.9600
O3—Cd1—O195.33 (14)H7A—C7—H7B109.5
O3—Cd1—N6138.84 (11)C8—C7—H7C109.5
O1—Cd1—N694.09 (13)H7A—C7—H7C109.5
O3—Cd1—N1110.04 (11)H7B—C7—H7C109.5
O1—Cd1—N170.52 (11)C9—C8—N2106.1 (4)
N6—Cd1—N1110.88 (11)C9—C8—C7127.7 (4)
O3—Cd1—N470.45 (11)N2—C8—C7126.2 (4)
O1—Cd1—N4108.27 (11)C8—C9—C10107.5 (4)
N6—Cd1—N468.54 (11)C8—C9—H9126.3
N1—Cd1—N4178.70 (11)C10—C9—H9126.3
O3—Cd1—N398.39 (13)N3—C10—C9110.2 (4)
O1—Cd1—N3139.29 (11)N3—C10—C11120.3 (4)
N6—Cd1—N3100.11 (12)C9—C10—C11129.6 (4)
N1—Cd1—N368.76 (11)C10—C11—H11A109.5
N4—Cd1—N3112.44 (11)C10—C11—H11B109.5
C6—N1—C2121.9 (3)H11A—C11—H11B109.5
C6—N1—Cd1121.2 (2)C10—C11—H11C109.5
C2—N1—Cd1116.8 (2)H11A—C11—H11C109.5
C8—N2—N3110.5 (3)H11B—C11—H11C109.5
C8—N2—C6131.3 (3)O4—C12—O3125.4 (4)
N3—N2—C6118.1 (3)O4—C12—C13119.1 (4)
C10—N3—N2105.7 (3)O3—C12—C13115.5 (4)
C10—N3—Cd1137.9 (3)N4—C13—C14119.0 (4)
N2—N3—Cd1116.4 (2)N4—C13—C12114.0 (3)
C17—N4—C13122.1 (3)C14—C13—C12127.0 (3)
C17—N4—Cd1120.9 (2)C13—C14—C15118.9 (4)
C13—N4—Cd1116.4 (2)C13—C14—Cl2123.1 (3)
C19—N5—N6110.3 (3)C15—C14—Cl2118.1 (3)
C19—N5—C17132.0 (3)C16—C15—C14121.3 (4)
N6—N5—C17117.6 (3)C16—C15—H15119.4
C21—N6—N5106.4 (3)C14—C15—H15119.4
C21—N6—Cd1135.9 (3)C15—C16—C17117.0 (4)
N5—N6—Cd1117.3 (2)C15—C16—H16121.5
C1—O1—Cd1121.6 (3)C17—C16—H16121.5
C12—O3—Cd1122.4 (3)N4—C17—C16121.6 (3)
H5A—O5—H5B108.5N4—C17—N5114.7 (3)
H6A—O6—H6B108.5C16—C17—N5123.6 (3)
H7D—O7—H7E108.5C19—C18—H18A109.5
H8A—O8—H8B108.5C19—C18—H18B109.5
O2—C1—O1125.3 (4)H18A—C18—H18B109.5
O2—C1—C2118.2 (4)C19—C18—H18C109.5
O1—C1—C2116.5 (4)H18A—C18—H18C109.5
N1—C2—C3118.9 (3)H18B—C18—H18C109.5
N1—C2—C1114.5 (4)C20—C19—N5105.8 (4)
C3—C2—C1126.6 (4)C20—C19—C18128.4 (4)
C4—C3—C2119.2 (4)N5—C19—C18125.7 (4)
C4—C3—Cl1116.7 (3)C19—C20—C21107.8 (4)
C2—C3—Cl1124.1 (3)C19—C20—H20126.1
C5—C4—C3120.9 (4)C21—C20—H20126.1
C5—C4—H4119.6N6—C21—C20109.6 (4)
C3—C4—H4119.6N6—C21—C22121.1 (4)
C4—C5—C6117.7 (4)C20—C21—C22129.3 (4)
C4—C5—H5121.1C21—C22—H22A109.5
C6—C5—H5121.1C21—C22—H22B109.5
N1—C6—C5121.4 (3)H22A—C22—H22B109.5
N1—C6—N2115.3 (3)C21—C22—H22C109.5
C5—C6—N2123.3 (3)H22A—C22—H22C109.5
C8—C7—H7A109.5H22B—C22—H22C109.5
C8—C7—H7B109.5
O3—Cd1—N1—C6−91.2 (3)N1—C2—C3—C4−0.3 (6)
O1—Cd1—N1—C6−179.9 (3)C1—C2—C3—C4−178.9 (4)
N6—Cd1—N1—C693.2 (3)N1—C2—C3—Cl1179.4 (3)
N4—Cd1—N1—C6157 (5)C1—C2—C3—Cl10.8 (6)
N3—Cd1—N1—C60.2 (3)C2—C3—C4—C50.3 (7)
O3—Cd1—N1—C286.4 (3)Cl1—C3—C4—C5−179.5 (4)
O1—Cd1—N1—C2−2.2 (3)C3—C4—C5—C6−0.9 (7)
N6—Cd1—N1—C2−89.1 (3)C2—N1—C6—C5−1.7 (6)
N4—Cd1—N1—C2−26 (5)Cd1—N1—C6—C5175.8 (3)
N3—Cd1—N1—C2177.8 (3)C2—N1—C6—N2180.0 (3)
C8—N2—N3—C10−0.3 (4)Cd1—N1—C6—N2−2.5 (4)
C6—N2—N3—C10177.2 (3)C4—C5—C6—N11.6 (6)
C8—N2—N3—Cd1177.9 (2)C4—C5—C6—N2179.8 (4)
C6—N2—N3—Cd1−4.6 (4)C8—N2—C6—N1−178.4 (4)
O3—Cd1—N3—C10−71.9 (4)N3—N2—C6—N14.7 (5)
O1—Cd1—N3—C10179.7 (4)C8—N2—C6—C53.3 (6)
N6—Cd1—N3—C1071.1 (4)N3—N2—C6—C5−173.7 (4)
N1—Cd1—N3—C10179.7 (4)N3—N2—C8—C90.0 (4)
N4—Cd1—N3—C100.3 (4)C6—N2—C8—C9−177.1 (4)
O3—Cd1—N3—N2110.6 (2)N3—N2—C8—C7−177.9 (4)
O1—Cd1—N3—N22.2 (3)C6—N2—C8—C75.0 (7)
N6—Cd1—N3—N2−106.3 (2)N2—C8—C9—C100.2 (5)
N1—Cd1—N3—N22.3 (2)C7—C8—C9—C10178.1 (4)
N4—Cd1—N3—N2−177.1 (2)N2—N3—C10—C90.5 (4)
O3—Cd1—N4—C17−173.3 (3)Cd1—N3—C10—C9−177.2 (3)
O1—Cd1—N4—C17−84.0 (3)N2—N3—C10—C11−179.8 (4)
N6—Cd1—N4—C173.1 (3)Cd1—N3—C10—C112.5 (7)
N1—Cd1—N4—C17−61 (5)C8—C9—C10—N3−0.4 (5)
N3—Cd1—N4—C1795.5 (3)C8—C9—C10—C11179.9 (5)
O3—Cd1—N4—C13−1.8 (3)Cd1—O3—C12—O4−168.9 (4)
O1—Cd1—N4—C1387.5 (3)Cd1—O3—C12—C1312.2 (5)
N6—Cd1—N4—C13174.6 (3)C17—N4—C13—C140.2 (5)
N1—Cd1—N4—C13111 (5)Cd1—N4—C13—C14−171.2 (3)
N3—Cd1—N4—C13−93.0 (3)C17—N4—C13—C12179.1 (3)
C19—N5—N6—C21−0.7 (4)Cd1—N4—C13—C127.7 (4)
C17—N5—N6—C21177.3 (3)O4—C12—C13—N4168.1 (4)
C19—N5—N6—Cd1173.2 (3)O3—C12—C13—N4−12.9 (5)
C17—N5—N6—Cd1−8.8 (4)O4—C12—C13—C14−13.1 (7)
O3—Cd1—N6—C21179.8 (4)O3—C12—C13—C14165.9 (4)
O1—Cd1—N6—C21−77.3 (4)N4—C13—C14—C150.4 (6)
N1—Cd1—N6—C21−6.6 (4)C12—C13—C14—C15−178.3 (4)
N4—Cd1—N6—C21174.6 (4)N4—C13—C14—Cl2−179.3 (3)
N3—Cd1—N6—C2164.4 (4)C12—C13—C14—Cl21.9 (6)
O3—Cd1—N6—N58.3 (4)C13—C14—C15—C160.1 (6)
O1—Cd1—N6—N5111.2 (3)Cl2—C14—C15—C16179.8 (3)
N1—Cd1—N6—N5−178.1 (2)C14—C15—C16—C17−1.1 (6)
N4—Cd1—N6—N53.2 (2)C13—N4—C17—C16−1.3 (6)
N3—Cd1—N6—N5−107.1 (3)Cd1—N4—C17—C16169.7 (3)
O3—Cd1—O1—C1−107.2 (4)C13—N4—C17—N5−179.6 (3)
N6—Cd1—O1—C1112.9 (4)Cd1—N4—C17—N5−8.6 (4)
N1—Cd1—O1—C12.2 (4)C15—C16—C17—N41.7 (6)
N4—Cd1—O1—C1−178.4 (4)C15—C16—C17—N5179.9 (4)
N3—Cd1—O1—C12.2 (5)C19—N5—C17—N4−171.2 (4)
O1—Cd1—O3—C12−113.7 (4)N6—N5—C17—N411.3 (5)
N6—Cd1—O3—C12−11.3 (5)C19—N5—C17—C1610.5 (6)
N1—Cd1—O3—C12175.1 (4)N6—N5—C17—C16−167.0 (3)
N4—Cd1—O3—C12−6.2 (4)N6—N5—C19—C200.5 (5)
N3—Cd1—O3—C12104.7 (4)C17—N5—C19—C20−177.1 (4)
Cd1—O1—C1—O2176.9 (5)N6—N5—C19—C18−176.8 (5)
Cd1—O1—C1—C2−1.8 (6)C17—N5—C19—C185.6 (8)
C6—N1—C2—C31.0 (5)N5—C19—C20—C21−0.1 (5)
Cd1—N1—C2—C3−176.6 (3)C18—C19—C20—C21177.1 (5)
C6—N1—C2—C1179.8 (4)N5—N6—C21—C200.6 (5)
Cd1—N1—C2—C12.2 (4)Cd1—N6—C21—C20−171.5 (3)
O2—C1—C2—N1−179.1 (5)N5—N6—C21—C22−178.5 (4)
O1—C1—C2—N1−0.4 (6)Cd1—N6—C21—C229.4 (7)
O2—C1—C2—C3−0.4 (8)C19—C20—C21—N6−0.3 (6)
O1—C1—C2—C3178.3 (4)C19—C20—C21—C22178.6 (5)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O2i0.852.313.155 (6)176
O5—H5B···O4ii0.852.032.883 (6)176
O6—H6A···O2iii0.851.962.804 (10)176
O6—H6B···O2iv0.852.293.135 (10)176
O7—H7D···O5v0.851.912.757 (9)176
O7—H7E···O8v0.852.022.866 (13)176
O8—H8A···O6v0.851.822.664 (13)177
O8—H8B···O7vi0.851.822.670 (15)177
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z−1; (iii) x+1, y, z; (iv) −x+1, −y, −z+1; (v) −x+1, −y+1, −z+1; (vi) x, y+1, z.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O2i0.852.313.155 (6)176
O5—H5B···O4ii0.852.032.883 (6)176
O6—H6A···O2iii0.851.962.804 (10)176
O6—H6B···O2iv0.852.293.135 (10)176
O7—H7D···O5v0.851.912.757 (9)176
O7—H7E···O8v0.852.022.866 (13)176
O8—H8A···O6v0.851.822.664 (13)177
O8—H8B···O7vi0.851.822.670 (15)177
Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z−1; (iii) x+1, y, z; (iv) −x+1, −y, −z+1; (v) −x+1, −y+1, −z+1; (vi) x, y+1, z.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (20761002) for support. This research was sponsored by the Fund of the Talent Highland Research Program of Guangxi University (205121), the Science Foundation of the State Ethnic Affairs Commission (07GX05), the Development Foundation of Guangxi Research Institute of Chemical Industry, and the Science Foundation of Guangxi University for Nationalities (0409032, 0409012,0509ZD047).

references
References top

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