Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055857/hg2342sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055857/hg2342Isup2.hkl |
CCDC reference: 665033
Key indicators
- Single-crystal X-ray study
- T = 298 K
- R factor = 0.037
- wR factor = 0.101
- Data-to-parameter ratio = 13.2
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
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%.
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).
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).
[Cd(C11H9ClN3O2)2]·4H2O | Z = 2 |
Mr = 685.79 | F(000) = 692 |
Triclinic, P1 | Dx = 1.689 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.179 (1) Å | Cell parameters from 3835 reflections |
b = 11.4140 (14) Å | θ = 2.6–27.6° |
c = 13.4240 (18) Å | µ = 1.07 mm−1 |
α = 114.745 (3)° | T = 298 K |
β = 102.249 (2)° | Block, colorless |
γ = 96.428 (1)° | 0.51 × 0.50 × 0.48 mm |
V = 1348.3 (3) Å3 |
Bruker SMART CCD area-detector diffractometer | 4645 independent reflections |
Radiation source: fine-focus sealed tube | 3752 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.020 |
phi and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→11 |
Tmin = 0.613, Tmax = 0.629 | k = −6→13 |
6989 measured reflections | l = −15→13 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0431P)2 + 1.4843P] where P = (Fo2 + 2Fc2)/3 |
4645 reflections | (Δ/σ)max < 0.001 |
352 parameters | Δρmax = 0.68 e Å−3 |
0 restraints | Δρmin = −0.60 e Å−3 |
[Cd(C11H9ClN3O2)2]·4H2O | γ = 96.428 (1)° |
Mr = 685.79 | V = 1348.3 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 10.179 (1) Å | Mo Kα radiation |
b = 11.4140 (14) Å | µ = 1.07 mm−1 |
c = 13.4240 (18) Å | T = 298 K |
α = 114.745 (3)° | 0.51 × 0.50 × 0.48 mm |
β = 102.249 (2)° |
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 = 0.629 | Rint = 0.020 |
6989 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.101 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.68 e Å−3 |
4645 reflections | Δρmin = −0.60 e Å−3 |
352 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cd1 | 0.28358 (3) | 0.52895 (3) | 0.75795 (3) | 0.04744 (13) | |
Cl1 | 0.28940 (15) | 0.04201 (12) | 0.81008 (14) | 0.0788 (4) | |
Cl2 | −0.05630 (14) | 0.92388 (12) | 0.82716 (12) | 0.0679 (4) | |
N1 | 0.3954 (3) | 0.3897 (3) | 0.8128 (2) | 0.0354 (7) | |
N2 | 0.5982 (3) | 0.5488 (3) | 0.8803 (3) | 0.0366 (7) | |
N3 | 0.5202 (3) | 0.6247 (3) | 0.8477 (3) | 0.0429 (8) | |
N4 | 0.1674 (3) | 0.6646 (3) | 0.6998 (3) | 0.0363 (7) | |
N5 | 0.2145 (3) | 0.5588 (3) | 0.5272 (3) | 0.0412 (7) | |
N6 | 0.2745 (3) | 0.4811 (3) | 0.5704 (3) | 0.0461 (8) | |
O1 | 0.1292 (3) | 0.3403 (4) | 0.7077 (3) | 0.0696 (10) | |
O2 | 0.0848 (4) | 0.1492 (4) | 0.7108 (5) | 0.1164 (18) | |
O3 | 0.2019 (4) | 0.6588 (4) | 0.8981 (3) | 0.0711 (10) | |
O4 | 0.1175 (5) | 0.8337 (4) | 0.9710 (3) | 0.0928 (13) | |
O5 | 0.1574 (4) | 0.7985 (4) | 0.1750 (3) | 0.0868 (11) | |
H5A | 0.0902 | 0.8134 | 0.2033 | 0.104* | |
H5B | 0.1419 | 0.8098 | 0.1152 | 0.104* | |
O6 | 0.8516 (7) | 0.0186 (7) | 0.5197 (7) | 0.194 (3) | |
H6A | 0.9247 | 0.0565 | 0.5755 | 0.232* | |
H6B | 0.8737 | −0.0257 | 0.4593 | 0.232* | |
O7 | 0.5992 (8) | 0.1002 (12) | 0.6502 (7) | 0.320 (7) | |
H7D | 0.6761 | 0.1315 | 0.7021 | 0.384* | |
H7E | 0.6127 | 0.0984 | 0.5893 | 0.384* | |
O8 | 0.3705 (9) | 0.9082 (10) | 0.5599 (7) | 0.252 (5) | |
H8A | 0.3011 | 0.9345 | 0.5363 | 0.303* | |
H8B | 0.4417 | 0.9709 | 0.5876 | 0.303* | |
C1 | 0.1637 (5) | 0.2515 (5) | 0.7311 (4) | 0.0619 (13) | |
C2 | 0.3166 (4) | 0.2746 (4) | 0.7924 (3) | 0.0411 (9) | |
C3 | 0.3773 (4) | 0.1916 (4) | 0.8290 (4) | 0.0471 (10) | |
C4 | 0.5165 (5) | 0.2285 (4) | 0.8846 (4) | 0.0583 (12) | |
H4 | 0.5579 | 0.1730 | 0.9091 | 0.070* | |
C5 | 0.5943 (4) | 0.3456 (4) | 0.9043 (4) | 0.0520 (11) | |
H5 | 0.6880 | 0.3714 | 0.9428 | 0.062* | |
C6 | 0.5290 (4) | 0.4244 (4) | 0.8650 (3) | 0.0348 (8) | |
C7 | 0.8520 (4) | 0.5611 (5) | 0.9700 (4) | 0.0592 (12) | |
H7A | 0.9379 | 0.6213 | 0.9900 | 0.089* | |
H7B | 0.8509 | 0.4762 | 0.9107 | 0.089* | |
H7C | 0.8418 | 0.5523 | 1.0362 | 0.089* | |
C8 | 0.7345 (4) | 0.6139 (4) | 0.9277 (3) | 0.0425 (9) | |
C9 | 0.7415 (5) | 0.7315 (4) | 0.9249 (4) | 0.0526 (11) | |
H9 | 0.8208 | 0.7975 | 0.9509 | 0.063* | |
C10 | 0.6079 (4) | 0.7357 (4) | 0.8756 (4) | 0.0479 (10) | |
C11 | 0.5576 (6) | 0.8428 (5) | 0.8524 (5) | 0.0756 (15) | |
H11A | 0.4841 | 0.8036 | 0.7821 | 0.113* | |
H11B | 0.6321 | 0.8962 | 0.8460 | 0.113* | |
H11C | 0.5243 | 0.8971 | 0.9141 | 0.113* | |
C12 | 0.1458 (4) | 0.7485 (4) | 0.8925 (4) | 0.0494 (10) | |
C13 | 0.1089 (4) | 0.7461 (4) | 0.7743 (3) | 0.0379 (8) | |
C14 | 0.0228 (4) | 0.8155 (4) | 0.7387 (4) | 0.0433 (9) | |
C15 | −0.0012 (4) | 0.7982 (4) | 0.6274 (4) | 0.0498 (10) | |
H15 | −0.0588 | 0.8445 | 0.6030 | 0.060* | |
C16 | 0.0583 (4) | 0.7141 (4) | 0.5526 (4) | 0.0458 (10) | |
H16 | 0.0411 | 0.7011 | 0.4775 | 0.055* | |
C17 | 0.1456 (4) | 0.6489 (4) | 0.5942 (3) | 0.0371 (8) | |
C18 | 0.1855 (6) | 0.5966 (7) | 0.3503 (5) | 0.0856 (18) | |
H18A | 0.2302 | 0.5746 | 0.2907 | 0.128* | |
H18B | 0.2100 | 0.6907 | 0.3978 | 0.128* | |
H18C | 0.0873 | 0.5682 | 0.3168 | 0.128* | |
C19 | 0.2308 (4) | 0.5284 (5) | 0.4213 (4) | 0.0521 (11) | |
C20 | 0.3009 (5) | 0.4300 (5) | 0.3984 (4) | 0.0618 (13) | |
H20 | 0.3274 | 0.3884 | 0.3322 | 0.074* | |
C21 | 0.3260 (4) | 0.4027 (4) | 0.4918 (4) | 0.0520 (11) | |
C22 | 0.3962 (6) | 0.3021 (5) | 0.5088 (5) | 0.0752 (15) | |
H22A | 0.4616 | 0.3425 | 0.5834 | 0.113* | |
H22B | 0.4434 | 0.2675 | 0.4516 | 0.113* | |
H22C | 0.3288 | 0.2313 | 0.5023 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cd1 | 0.04307 (19) | 0.0611 (2) | 0.0546 (2) | 0.02603 (15) | 0.01381 (14) | 0.03812 (16) |
Cl1 | 0.0807 (9) | 0.0469 (7) | 0.1047 (11) | 0.0000 (6) | 0.0116 (8) | 0.0413 (7) |
Cl2 | 0.0791 (8) | 0.0659 (7) | 0.0984 (10) | 0.0460 (7) | 0.0555 (8) | 0.0525 (7) |
N1 | 0.0331 (16) | 0.0381 (17) | 0.0355 (16) | 0.0099 (13) | 0.0052 (13) | 0.0188 (14) |
N2 | 0.0322 (16) | 0.0397 (17) | 0.0433 (18) | 0.0124 (14) | 0.0090 (14) | 0.0235 (15) |
N3 | 0.0434 (19) | 0.0458 (19) | 0.050 (2) | 0.0178 (16) | 0.0146 (16) | 0.0289 (16) |
N4 | 0.0327 (16) | 0.0420 (17) | 0.0405 (18) | 0.0120 (14) | 0.0097 (14) | 0.0242 (14) |
N5 | 0.0399 (18) | 0.0475 (19) | 0.0367 (18) | 0.0136 (15) | 0.0072 (14) | 0.0204 (15) |
N6 | 0.050 (2) | 0.0453 (19) | 0.048 (2) | 0.0194 (16) | 0.0143 (16) | 0.0230 (16) |
O1 | 0.0348 (16) | 0.094 (3) | 0.089 (2) | 0.0062 (16) | −0.0037 (16) | 0.063 (2) |
O2 | 0.059 (2) | 0.095 (3) | 0.180 (5) | −0.020 (2) | −0.024 (3) | 0.085 (3) |
O3 | 0.086 (2) | 0.108 (3) | 0.0575 (19) | 0.066 (2) | 0.0353 (18) | 0.056 (2) |
O4 | 0.154 (4) | 0.099 (3) | 0.058 (2) | 0.078 (3) | 0.054 (2) | 0.042 (2) |
O5 | 0.092 (3) | 0.102 (3) | 0.079 (3) | 0.045 (2) | 0.029 (2) | 0.044 (2) |
O6 | 0.153 (6) | 0.172 (6) | 0.193 (7) | 0.002 (5) | −0.010 (5) | 0.061 (5) |
O7 | 0.161 (7) | 0.516 (18) | 0.122 (6) | −0.095 (9) | 0.018 (5) | 0.049 (8) |
O8 | 0.207 (8) | 0.286 (11) | 0.192 (8) | 0.021 (8) | 0.069 (7) | 0.045 (8) |
C1 | 0.043 (2) | 0.066 (3) | 0.074 (3) | 0.000 (2) | 0.000 (2) | 0.039 (3) |
C2 | 0.040 (2) | 0.041 (2) | 0.039 (2) | 0.0070 (18) | 0.0069 (17) | 0.0176 (17) |
C3 | 0.054 (3) | 0.037 (2) | 0.051 (2) | 0.0104 (19) | 0.011 (2) | 0.0229 (19) |
C4 | 0.058 (3) | 0.045 (3) | 0.076 (3) | 0.016 (2) | 0.006 (2) | 0.037 (2) |
C5 | 0.040 (2) | 0.052 (3) | 0.069 (3) | 0.012 (2) | 0.004 (2) | 0.037 (2) |
C6 | 0.0330 (19) | 0.038 (2) | 0.0331 (19) | 0.0126 (16) | 0.0072 (16) | 0.0166 (16) |
C7 | 0.035 (2) | 0.077 (3) | 0.068 (3) | 0.008 (2) | 0.004 (2) | 0.042 (3) |
C8 | 0.039 (2) | 0.050 (2) | 0.042 (2) | 0.0084 (18) | 0.0131 (18) | 0.0239 (19) |
C9 | 0.049 (3) | 0.052 (3) | 0.054 (3) | −0.001 (2) | 0.014 (2) | 0.025 (2) |
C10 | 0.056 (3) | 0.046 (2) | 0.055 (3) | 0.016 (2) | 0.023 (2) | 0.031 (2) |
C11 | 0.086 (4) | 0.058 (3) | 0.104 (4) | 0.022 (3) | 0.031 (3) | 0.053 (3) |
C12 | 0.048 (2) | 0.062 (3) | 0.050 (3) | 0.023 (2) | 0.022 (2) | 0.030 (2) |
C13 | 0.035 (2) | 0.040 (2) | 0.047 (2) | 0.0115 (17) | 0.0160 (17) | 0.0248 (18) |
C14 | 0.040 (2) | 0.041 (2) | 0.064 (3) | 0.0161 (18) | 0.024 (2) | 0.033 (2) |
C15 | 0.042 (2) | 0.056 (3) | 0.073 (3) | 0.022 (2) | 0.016 (2) | 0.046 (2) |
C16 | 0.043 (2) | 0.054 (2) | 0.048 (2) | 0.0135 (19) | 0.0087 (19) | 0.033 (2) |
C17 | 0.0321 (19) | 0.042 (2) | 0.041 (2) | 0.0068 (16) | 0.0073 (16) | 0.0236 (17) |
C18 | 0.092 (4) | 0.137 (5) | 0.063 (3) | 0.055 (4) | 0.038 (3) | 0.063 (4) |
C19 | 0.048 (2) | 0.070 (3) | 0.040 (2) | 0.017 (2) | 0.0142 (19) | 0.025 (2) |
C20 | 0.061 (3) | 0.076 (3) | 0.045 (3) | 0.025 (3) | 0.023 (2) | 0.018 (2) |
C21 | 0.046 (2) | 0.054 (3) | 0.053 (3) | 0.018 (2) | 0.016 (2) | 0.019 (2) |
C22 | 0.079 (4) | 0.068 (3) | 0.088 (4) | 0.043 (3) | 0.032 (3) | 0.033 (3) |
Cd1—O3 | 2.243 (3) | C3—C4 | 1.377 (6) |
Cd1—O1 | 2.266 (3) | C4—C5 | 1.364 (6) |
Cd1—N6 | 2.320 (3) | C4—H4 | 0.9300 |
Cd1—N1 | 2.322 (3) | C5—C6 | 1.383 (5) |
Cd1—N4 | 2.331 (3) | C5—H5 | 0.9300 |
Cd1—N3 | 2.350 (3) | C7—C8 | 1.508 (6) |
Cl1—C3 | 1.726 (4) | C7—H7A | 0.9600 |
Cl2—C14 | 1.728 (4) | C7—H7B | 0.9600 |
N1—C6 | 1.319 (4) | C7—H7C | 0.9600 |
N1—C2 | 1.346 (5) | C8—C9 | 1.353 (6) |
N2—C8 | 1.371 (5) | C9—C10 | 1.396 (6) |
N2—N3 | 1.378 (4) | C9—H9 | 0.9300 |
N2—C6 | 1.423 (5) | C10—C11 | 1.498 (6) |
N3—C10 | 1.323 (5) | C11—H11A | 0.9600 |
N4—C17 | 1.317 (5) | C11—H11B | 0.9600 |
N4—C13 | 1.348 (5) | C11—H11C | 0.9600 |
N5—C19 | 1.368 (5) | C12—C13 | 1.539 (6) |
N5—N6 | 1.378 (4) | C13—C14 | 1.385 (5) |
N5—C17 | 1.419 (5) | C14—C15 | 1.385 (6) |
N6—C21 | 1.318 (5) | C15—C16 | 1.370 (6) |
O1—C1 | 1.245 (5) | C15—H15 | 0.9300 |
O2—C1 | 1.230 (6) | C16—C17 | 1.393 (5) |
O3—C12 | 1.248 (5) | C16—H16 | 0.9300 |
O4—C12 | 1.213 (5) | C18—C19 | 1.498 (7) |
O5—H5A | 0.8500 | C18—H18A | 0.9600 |
O5—H5B | 0.8501 | C18—H18B | 0.9600 |
O6—H6A | 0.8500 | C18—H18C | 0.9600 |
O6—H6B | 0.8500 | C19—C20 | 1.359 (6) |
O7—H7D | 0.8500 | C20—C21 | 1.394 (7) |
O7—H7E | 0.8501 | C20—H20 | 0.9300 |
O8—H8A | 0.8500 | C21—C22 | 1.489 (6) |
O8—H8B | 0.8501 | C22—H22A | 0.9600 |
C1—C2 | 1.533 (6) | C22—H22B | 0.9600 |
C2—C3 | 1.384 (5) | C22—H22C | 0.9600 |
O3—Cd1—O1 | 95.33 (14) | H7A—C7—H7B | 109.5 |
O3—Cd1—N6 | 138.84 (11) | C8—C7—H7C | 109.5 |
O1—Cd1—N6 | 94.09 (13) | H7A—C7—H7C | 109.5 |
O3—Cd1—N1 | 110.04 (11) | H7B—C7—H7C | 109.5 |
O1—Cd1—N1 | 70.52 (11) | C9—C8—N2 | 106.1 (4) |
N6—Cd1—N1 | 110.88 (11) | C9—C8—C7 | 127.7 (4) |
O3—Cd1—N4 | 70.45 (11) | N2—C8—C7 | 126.2 (4) |
O1—Cd1—N4 | 108.27 (11) | C8—C9—C10 | 107.5 (4) |
N6—Cd1—N4 | 68.54 (11) | C8—C9—H9 | 126.3 |
N1—Cd1—N4 | 178.70 (11) | C10—C9—H9 | 126.3 |
O3—Cd1—N3 | 98.39 (13) | N3—C10—C9 | 110.2 (4) |
O1—Cd1—N3 | 139.29 (11) | N3—C10—C11 | 120.3 (4) |
N6—Cd1—N3 | 100.11 (12) | C9—C10—C11 | 129.6 (4) |
N1—Cd1—N3 | 68.76 (11) | C10—C11—H11A | 109.5 |
N4—Cd1—N3 | 112.44 (11) | C10—C11—H11B | 109.5 |
C6—N1—C2 | 121.9 (3) | H11A—C11—H11B | 109.5 |
C6—N1—Cd1 | 121.2 (2) | C10—C11—H11C | 109.5 |
C2—N1—Cd1 | 116.8 (2) | H11A—C11—H11C | 109.5 |
C8—N2—N3 | 110.5 (3) | H11B—C11—H11C | 109.5 |
C8—N2—C6 | 131.3 (3) | O4—C12—O3 | 125.4 (4) |
N3—N2—C6 | 118.1 (3) | O4—C12—C13 | 119.1 (4) |
C10—N3—N2 | 105.7 (3) | O3—C12—C13 | 115.5 (4) |
C10—N3—Cd1 | 137.9 (3) | N4—C13—C14 | 119.0 (4) |
N2—N3—Cd1 | 116.4 (2) | N4—C13—C12 | 114.0 (3) |
C17—N4—C13 | 122.1 (3) | C14—C13—C12 | 127.0 (3) |
C17—N4—Cd1 | 120.9 (2) | C13—C14—C15 | 118.9 (4) |
C13—N4—Cd1 | 116.4 (2) | C13—C14—Cl2 | 123.1 (3) |
C19—N5—N6 | 110.3 (3) | C15—C14—Cl2 | 118.1 (3) |
C19—N5—C17 | 132.0 (3) | C16—C15—C14 | 121.3 (4) |
N6—N5—C17 | 117.6 (3) | C16—C15—H15 | 119.4 |
C21—N6—N5 | 106.4 (3) | C14—C15—H15 | 119.4 |
C21—N6—Cd1 | 135.9 (3) | C15—C16—C17 | 117.0 (4) |
N5—N6—Cd1 | 117.3 (2) | C15—C16—H16 | 121.5 |
C1—O1—Cd1 | 121.6 (3) | C17—C16—H16 | 121.5 |
C12—O3—Cd1 | 122.4 (3) | N4—C17—C16 | 121.6 (3) |
H5A—O5—H5B | 108.5 | N4—C17—N5 | 114.7 (3) |
H6A—O6—H6B | 108.5 | C16—C17—N5 | 123.6 (3) |
H7D—O7—H7E | 108.5 | C19—C18—H18A | 109.5 |
H8A—O8—H8B | 108.5 | C19—C18—H18B | 109.5 |
O2—C1—O1 | 125.3 (4) | H18A—C18—H18B | 109.5 |
O2—C1—C2 | 118.2 (4) | C19—C18—H18C | 109.5 |
O1—C1—C2 | 116.5 (4) | H18A—C18—H18C | 109.5 |
N1—C2—C3 | 118.9 (3) | H18B—C18—H18C | 109.5 |
N1—C2—C1 | 114.5 (4) | C20—C19—N5 | 105.8 (4) |
C3—C2—C1 | 126.6 (4) | C20—C19—C18 | 128.4 (4) |
C4—C3—C2 | 119.2 (4) | N5—C19—C18 | 125.7 (4) |
C4—C3—Cl1 | 116.7 (3) | C19—C20—C21 | 107.8 (4) |
C2—C3—Cl1 | 124.1 (3) | C19—C20—H20 | 126.1 |
C5—C4—C3 | 120.9 (4) | C21—C20—H20 | 126.1 |
C5—C4—H4 | 119.6 | N6—C21—C20 | 109.6 (4) |
C3—C4—H4 | 119.6 | N6—C21—C22 | 121.1 (4) |
C4—C5—C6 | 117.7 (4) | C20—C21—C22 | 129.3 (4) |
C4—C5—H5 | 121.1 | C21—C22—H22A | 109.5 |
C6—C5—H5 | 121.1 | C21—C22—H22B | 109.5 |
N1—C6—C5 | 121.4 (3) | H22A—C22—H22B | 109.5 |
N1—C6—N2 | 115.3 (3) | C21—C22—H22C | 109.5 |
C5—C6—N2 | 123.3 (3) | H22A—C22—H22C | 109.5 |
C8—C7—H7A | 109.5 | H22B—C22—H22C | 109.5 |
C8—C7—H7B | 109.5 | ||
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—C6 | 93.2 (3) | N1—C2—C3—Cl1 | 179.4 (3) |
N4—Cd1—N1—C6 | 157 (5) | C1—C2—C3—Cl1 | 0.8 (6) |
N3—Cd1—N1—C6 | 0.2 (3) | C2—C3—C4—C5 | 0.3 (7) |
O3—Cd1—N1—C2 | 86.4 (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—C5 | 175.8 (3) |
N3—Cd1—N1—C2 | 177.8 (3) | C2—N1—C6—N2 | 180.0 (3) |
C8—N2—N3—C10 | −0.3 (4) | Cd1—N1—C6—N2 | −2.5 (4) |
C6—N2—N3—C10 | 177.2 (3) | C4—C5—C6—N1 | 1.6 (6) |
C8—N2—N3—Cd1 | 177.9 (2) | C4—C5—C6—N2 | 179.8 (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—N1 | 4.7 (5) |
O1—Cd1—N3—C10 | 179.7 (4) | C8—N2—C6—C5 | 3.3 (6) |
N6—Cd1—N3—C10 | 71.1 (4) | N3—N2—C6—C5 | −173.7 (4) |
N1—Cd1—N3—C10 | 179.7 (4) | N3—N2—C8—C9 | 0.0 (4) |
N4—Cd1—N3—C10 | 0.3 (4) | C6—N2—C8—C9 | −177.1 (4) |
O3—Cd1—N3—N2 | 110.6 (2) | N3—N2—C8—C7 | −177.9 (4) |
O1—Cd1—N3—N2 | 2.2 (3) | C6—N2—C8—C7 | 5.0 (7) |
N6—Cd1—N3—N2 | −106.3 (2) | N2—C8—C9—C10 | 0.2 (5) |
N1—Cd1—N3—N2 | 2.3 (2) | C7—C8—C9—C10 | 178.1 (4) |
N4—Cd1—N3—N2 | −177.1 (2) | N2—N3—C10—C9 | 0.5 (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—C17 | 3.1 (3) | Cd1—N3—C10—C11 | 2.5 (7) |
N1—Cd1—N4—C17 | −61 (5) | C8—C9—C10—N3 | −0.4 (5) |
N3—Cd1—N4—C17 | 95.5 (3) | C8—C9—C10—C11 | 179.9 (5) |
O3—Cd1—N4—C13 | −1.8 (3) | Cd1—O3—C12—O4 | −168.9 (4) |
O1—Cd1—N4—C13 | 87.5 (3) | Cd1—O3—C12—C13 | 12.2 (5) |
N6—Cd1—N4—C13 | 174.6 (3) | C17—N4—C13—C14 | 0.2 (5) |
N1—Cd1—N4—C13 | 111 (5) | Cd1—N4—C13—C14 | −171.2 (3) |
N3—Cd1—N4—C13 | −93.0 (3) | C17—N4—C13—C12 | 179.1 (3) |
C19—N5—N6—C21 | −0.7 (4) | Cd1—N4—C13—C12 | 7.7 (4) |
C17—N5—N6—C21 | 177.3 (3) | O4—C12—C13—N4 | 168.1 (4) |
C19—N5—N6—Cd1 | 173.2 (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—C21 | 179.8 (4) | O3—C12—C13—C14 | 165.9 (4) |
O1—Cd1—N6—C21 | −77.3 (4) | N4—C13—C14—C15 | 0.4 (6) |
N1—Cd1—N6—C21 | −6.6 (4) | C12—C13—C14—C15 | −178.3 (4) |
N4—Cd1—N6—C21 | 174.6 (4) | N4—C13—C14—Cl2 | −179.3 (3) |
N3—Cd1—N6—C21 | 64.4 (4) | C12—C13—C14—Cl2 | 1.9 (6) |
O3—Cd1—N6—N5 | 8.3 (4) | C13—C14—C15—C16 | 0.1 (6) |
O1—Cd1—N6—N5 | 111.2 (3) | Cl2—C14—C15—C16 | 179.8 (3) |
N1—Cd1—N6—N5 | −178.1 (2) | C14—C15—C16—C17 | −1.1 (6) |
N4—Cd1—N6—N5 | 3.2 (2) | C13—N4—C17—C16 | −1.3 (6) |
N3—Cd1—N6—N5 | −107.1 (3) | Cd1—N4—C17—C16 | 169.7 (3) |
O3—Cd1—O1—C1 | −107.2 (4) | C13—N4—C17—N5 | −179.6 (3) |
N6—Cd1—O1—C1 | 112.9 (4) | Cd1—N4—C17—N5 | −8.6 (4) |
N1—Cd1—O1—C1 | 2.2 (4) | C15—C16—C17—N4 | 1.7 (6) |
N4—Cd1—O1—C1 | −178.4 (4) | C15—C16—C17—N5 | 179.9 (4) |
N3—Cd1—O1—C1 | 2.2 (5) | C19—N5—C17—N4 | −171.2 (4) |
O1—Cd1—O3—C12 | −113.7 (4) | N6—N5—C17—N4 | 11.3 (5) |
N6—Cd1—O3—C12 | −11.3 (5) | C19—N5—C17—C16 | 10.5 (6) |
N1—Cd1—O3—C12 | 175.1 (4) | N6—N5—C17—C16 | −167.0 (3) |
N4—Cd1—O3—C12 | −6.2 (4) | N6—N5—C19—C20 | 0.5 (5) |
N3—Cd1—O3—C12 | 104.7 (4) | C17—N5—C19—C20 | −177.1 (4) |
Cd1—O1—C1—O2 | 176.9 (5) | N6—N5—C19—C18 | −176.8 (5) |
Cd1—O1—C1—C2 | −1.8 (6) | C17—N5—C19—C18 | 5.6 (8) |
C6—N1—C2—C3 | 1.0 (5) | N5—C19—C20—C21 | −0.1 (5) |
Cd1—N1—C2—C3 | −176.6 (3) | C18—C19—C20—C21 | 177.1 (5) |
C6—N1—C2—C1 | 179.8 (4) | N5—N6—C21—C20 | 0.6 (5) |
Cd1—N1—C2—C1 | 2.2 (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—C22 | 9.4 (7) |
O2—C1—C2—C3 | −0.4 (8) | C19—C20—C21—N6 | −0.3 (6) |
O1—C1—C2—C3 | 178.3 (4) | C19—C20—C21—C22 | 178.6 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2i | 0.85 | 2.31 | 3.155 (6) | 176 |
O5—H5B···O4ii | 0.85 | 2.03 | 2.883 (6) | 176 |
O6—H6A···O2iii | 0.85 | 1.96 | 2.804 (10) | 176 |
O6—H6B···O2iv | 0.85 | 2.29 | 3.135 (10) | 176 |
O7—H7D···O5v | 0.85 | 1.91 | 2.757 (9) | 176 |
O7—H7E···O8v | 0.85 | 2.02 | 2.866 (13) | 176 |
O8—H8A···O6v | 0.85 | 1.82 | 2.664 (13) | 177 |
O8—H8B···O7vi | 0.85 | 1.82 | 2.670 (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. |
Experimental details
Crystal data | |
Chemical formula | [Cd(C11H9ClN3O2)2]·4H2O |
Mr | 685.79 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 10.179 (1), 11.4140 (14), 13.4240 (18) |
α, β, γ (°) | 114.745 (3), 102.249 (2), 96.428 (1) |
V (Å3) | 1348.3 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.07 |
Crystal size (mm) | 0.51 × 0.50 × 0.48 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.613, 0.629 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6989, 4645, 3752 |
Rint | 0.020 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.101, 1.05 |
No. of reflections | 4645 |
No. of parameters | 352 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.68, −0.60 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2i | 0.85 | 2.306 | 3.155 (6) | 176.27 |
O5—H5B···O4ii | 0.85 | 2.034 | 2.883 (6) | 176.09 |
O6—H6A···O2iii | 0.85 | 1.956 | 2.804 (10) | 175.97 |
O6—H6B···O2iv | 0.85 | 2.286 | 3.135 (10) | 175.48 |
O7—H7D···O5v | 0.85 | 1.908 | 2.757 (9) | 176.44 |
O7—H7E···O8v | 0.85 | 2.017 | 2.866 (13) | 175.74 |
O8—H8A···O6v | 0.85 | 1.815 | 2.664 (13) | 176.86 |
O8—H8B···O7vi | 0.85 | 1.821 | 2.670 (15) | 176.83 |
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. |
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).