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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807061533/at2502sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807061533/at2502Isup2.hkl |
CCDC reference: 674164
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean
(C-C) = 0.005 Å
- R factor = 0.038
- wR factor = 0.118
- Data-to-parameter ratio = 15.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.98 PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - O1 .. 9.75 su PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - O2 .. 8.96 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Zn1 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C18 PLAT731_ALERT_1_C Bond Calc 0.89(4), Rep 0.883(19) ...... 2.11 su-Ra O2 -H21O 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.89(4), Rep 0.881(19) ...... 2.11 su-Ra O2 -H22O 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(4), Rep 0.883(19) ...... 2.11 su-Ra O2 -H21O 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.89(4), Rep 0.881(19) ...... 2.11 su-Ra O2 -H22O 1.555 1.555
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 9 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
The ligand was obtained according to the procedure previously described (Xue et al., 2000). Compound (I) was prepared by a literature procedure (Macías et al., 2003). Single crystals of (I) suitable for X-ray data collection appeared after a few days from a methanol solution.
The O-bound H atoms were located in difference map and were refined with restrained geometry (Nardelli, 1999), viz. O—H distances were restrained to 0.85 (2) Å and H···H distances were restrained to 1.365 (2) Å, thus leading to the angle of 107°.
The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93Å (aromatic), 0.96Å (methyl). All H atoms were refined with isotropic displacement parameters (set to 1.2 or 1.5 times of the Ueq of the parent atom).
The interest to develop the coordination chemistry of pyrazolone derivatives is because of their biological and medicinal properties. They present a variety of biological activities ranging from anti-tumour, fungicide, bactericide, antiinflamatory and anti-viral activities (Prasad and Agarwal, 2007; Hernández-Delgadillo et al., 2006; Raman et al., 2003; Burdulene et al., 1999). As part of our efforts to investigate transition metal (II) complexes based on 4-aminoantypirine derivatives and sulfonamide pharmacophoric group, we describe the X-ray characterization of the title compound, (I).
The ZnII ion has a tetrahedral coordination formed by the two sulfonamide N atoms and the two water molecules (Table 1). The bond angles around the central Zn atom are close to the 109° angle of an ideal tetrahedral value. Both hydrogen atoms of each water molecule are involved in an intermolecular O—H···O [O—H···O = 2.52 (3) Å, O—H···O = 2.05 (3) Å, respectively] and an intramolecular O—H···O [O—H···O = 2.06 (2) Å, O—H···O = 2.22 (3) Å, respectively] hydrogen bonds (Table 2).
For related literature, see: Burdulene et al. (1999); Hernández-Delgadillo & Cruz (2006); Macías et al. (2003); Nardelli (1999); Prasad & Agarwal (2007); Raman et al. (2003); Xue et al. (2000).
Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
![]() | Fig. 1. Molecular structure of (I), showing the atom labeling and displacement ellipsoids drawn at the 50% probability level. |
[Zn(C17H14Cl2N3O3S)2(H2O)2] | F(000) = 1888 |
Mr = 923.95 | Dx = 1.568 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 8931 reflections |
a = 15.0683 (7) Å | θ = 1.9–25.0° |
b = 12.3009 (5) Å | µ = 1.07 mm−1 |
c = 21.8256 (9) Å | T = 299 K |
β = 104.681 (4)° | Prism, colourless |
V = 3913.4 (3) Å3 | 0.50 × 0.42 × 0.36 mm |
Z = 4 |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 7987 independent reflections |
Radiation source: fine-focus sealed tube | 5392 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
Rotation method data acquisition using ω and phi scans. | θmax = 26.4°, θmin = 2.2° |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | h = −18→18 |
Tmin = 0.597, Tmax = 0.698 | k = −11→15 |
29052 measured reflections | l = −27→27 |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0463P)2 + 4.1837P] where P = (Fo2 + 2Fc2)/3 |
7987 reflections | (Δ/σ)max = 0.001 |
512 parameters | Δρmax = 0.73 e Å−3 |
6 restraints | Δρmin = −0.56 e Å−3 |
[Zn(C17H14Cl2N3O3S)2(H2O)2] | V = 3913.4 (3) Å3 |
Mr = 923.95 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.0683 (7) Å | µ = 1.07 mm−1 |
b = 12.3009 (5) Å | T = 299 K |
c = 21.8256 (9) Å | 0.50 × 0.42 × 0.36 mm |
β = 104.681 (4)° |
Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector | 7987 independent reflections |
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007) | 5392 reflections with I > 2σ(I) |
Tmin = 0.597, Tmax = 0.698 | Rint = 0.023 |
29052 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 6 restraints |
wR(F2) = 0.118 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.73 e Å−3 |
7987 reflections | Δρmin = −0.56 e Å−3 |
512 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 | ||
C1 | 0.5603 (2) | 0.6796 (3) | 0.28912 (16) | 0.0409 (7) | |
C2 | 0.5768 (2) | 0.6727 (3) | 0.35422 (16) | 0.0440 (8) | |
H2 | 0.5301 | 0.6517 | 0.3725 | 0.053* | |
C3 | 0.6630 (2) | 0.6972 (3) | 0.39213 (17) | 0.0494 (9) | |
C4 | 0.7332 (2) | 0.7298 (3) | 0.36661 (19) | 0.0527 (9) | |
H4 | 0.7902 | 0.7481 | 0.3927 | 0.063* | |
C5 | 0.7176 (2) | 0.7347 (3) | 0.3020 (2) | 0.0530 (9) | |
H5 | 0.7647 | 0.7554 | 0.2841 | 0.064* | |
C6 | 0.6323 (2) | 0.7093 (3) | 0.26338 (17) | 0.0469 (8) | |
C7 | 0.4364 (2) | 0.4486 (2) | 0.24139 (14) | 0.0333 (7) | |
C8 | 0.5111 (2) | 0.3709 (3) | 0.25951 (14) | 0.0346 (7) | |
C9 | 0.3639 (2) | 0.4081 (3) | 0.25942 (15) | 0.0383 (7) | |
C10 | 0.5135 (2) | 0.1837 (3) | 0.30486 (14) | 0.0389 (7) | |
C11 | 0.6071 (2) | 0.1694 (3) | 0.32822 (15) | 0.0439 (8) | |
H11 | 0.6464 | 0.2290 | 0.3344 | 0.053* | |
C12 | 0.6417 (3) | 0.0660 (3) | 0.34219 (17) | 0.0528 (9) | |
H12 | 0.7046 | 0.0560 | 0.3576 | 0.063* | |
C13 | 0.5844 (3) | −0.0222 (3) | 0.33367 (18) | 0.0583 (10) | |
H13 | 0.6083 | −0.0913 | 0.3442 | 0.070* | |
C14 | 0.4915 (3) | −0.0087 (3) | 0.3095 (2) | 0.0577 (10) | |
H14 | 0.4527 | −0.0687 | 0.3029 | 0.069* | |
C15 | 0.4561 (2) | 0.0943 (3) | 0.29522 (17) | 0.0477 (8) | |
H15 | 0.3932 | 0.1036 | 0.2790 | 0.057* | |
C16 | 0.2069 (2) | 0.3622 (3) | 0.00350 (14) | 0.0396 (7) | |
C17 | 0.1821 (2) | 0.2601 (3) | −0.02154 (16) | 0.0466 (8) | |
H17 | 0.2209 | 0.2220 | −0.0408 | 0.056* | |
C18 | 0.1005 (3) | 0.2152 (4) | −0.0180 (2) | 0.0654 (11) | |
C19 | 0.0418 (3) | 0.2701 (5) | 0.0092 (2) | 0.0807 (15) | |
H19 | −0.0139 | 0.2390 | 0.0106 | 0.097* | |
C20 | 0.0652 (3) | 0.3710 (5) | 0.0345 (2) | 0.0777 (15) | |
H20 | 0.0253 | 0.4087 | 0.0531 | 0.093* | |
C21 | 0.1481 (2) | 0.4170 (3) | 0.03238 (17) | 0.0557 (10) | |
C22 | 0.4052 (2) | 0.2880 (2) | 0.08708 (13) | 0.0334 (7) | |
C23 | 0.4841 (2) | 0.2373 (3) | 0.07336 (14) | 0.0350 (7) | |
C24 | 0.3656 (2) | 0.2139 (3) | 0.11794 (14) | 0.0360 (7) | |
C25 | 0.5654 (2) | 0.0663 (3) | 0.11081 (16) | 0.0399 (7) | |
C26 | 0.6037 (2) | 0.0348 (3) | 0.06249 (17) | 0.0479 (8) | |
H26 | 0.5750 | 0.0518 | 0.0206 | 0.057* | |
C27 | 0.6851 (3) | −0.0223 (3) | 0.0771 (2) | 0.0608 (10) | |
H27 | 0.7117 | −0.0434 | 0.0449 | 0.073* | |
C28 | 0.7271 (3) | −0.0482 (3) | 0.1386 (2) | 0.0641 (11) | |
H28 | 0.7824 | −0.0860 | 0.1481 | 0.077* | |
C29 | 0.6876 (3) | −0.0182 (3) | 0.1860 (2) | 0.0616 (10) | |
H29 | 0.7156 | −0.0371 | 0.2277 | 0.074* | |
C30 | 0.6065 (2) | 0.0399 (3) | 0.17273 (17) | 0.0492 (8) | |
H30 | 0.5802 | 0.0609 | 0.2051 | 0.059* | |
C31 | 0.2695 (2) | 0.4531 (3) | 0.25029 (19) | 0.0547 (9) | |
H31A | 0.2563 | 0.5015 | 0.2146 | 0.066* | |
H31B | 0.2656 | 0.4920 | 0.2876 | 0.066* | |
H31C | 0.2258 | 0.3946 | 0.2427 | 0.066* | |
C32 | 0.3580 (3) | 0.2902 (4) | 0.34843 (19) | 0.0653 (11) | |
H32A | 0.3842 | 0.2232 | 0.3673 | 0.078* | |
H32B | 0.2924 | 0.2865 | 0.3401 | 0.078* | |
H32C | 0.3803 | 0.3492 | 0.3769 | 0.078* | |
C33 | 0.2803 (2) | 0.2221 (3) | 0.14020 (16) | 0.0452 (8) | |
H33A | 0.2929 | 0.1995 | 0.1837 | 0.054* | |
H33B | 0.2340 | 0.1760 | 0.1147 | 0.054* | |
H33C | 0.2592 | 0.2960 | 0.1366 | 0.054* | |
C34 | 0.3762 (3) | 0.0120 (3) | 0.1241 (2) | 0.0578 (10) | |
H34A | 0.4233 | −0.0411 | 0.1395 | 0.069* | |
H34B | 0.3460 | −0.0036 | 0.0808 | 0.069* | |
H34C | 0.3324 | 0.0096 | 0.1493 | 0.069* | |
N1 | 0.44014 (18) | 0.5439 (2) | 0.20587 (12) | 0.0362 (6) | |
N2 | 0.47815 (17) | 0.2898 (2) | 0.29227 (12) | 0.0380 (6) | |
N3 | 0.38412 (17) | 0.3080 (2) | 0.28874 (13) | 0.0418 (6) | |
N4 | 0.37893 (17) | 0.3976 (2) | 0.07149 (11) | 0.0359 (6) | |
N5 | 0.48516 (17) | 0.1322 (2) | 0.09505 (12) | 0.0382 (6) | |
N6 | 0.41734 (17) | 0.1203 (2) | 0.12843 (12) | 0.0391 (6) | |
O1 | 0.5833 (2) | 0.4718 (3) | 0.12585 (15) | 0.0683 (8) | |
H11O | 0.625 (2) | 0.516 (3) | 0.118 (2) | 0.082* | |
H12O | 0.582 (3) | 0.418 (2) | 0.0979 (17) | 0.082* | |
O2 | 0.4242 (3) | 0.6670 (3) | 0.07039 (15) | 0.0901 (11) | |
H21O | 0.431 (4) | 0.721 (3) | 0.0980 (18) | 0.108* | |
H22O | 0.451 (3) | 0.692 (4) | 0.0415 (17) | 0.108* | |
O3 | 0.39205 (16) | 0.6519 (2) | 0.28993 (11) | 0.0501 (6) | |
O4 | 0.42301 (18) | 0.74189 (19) | 0.19750 (12) | 0.0553 (6) | |
O5 | 0.34501 (15) | 0.3405 (2) | −0.04321 (10) | 0.0480 (6) | |
O6 | 0.30904 (17) | 0.5236 (2) | −0.01506 (11) | 0.0535 (6) | |
O7 | 0.58658 (14) | 0.3693 (2) | 0.24759 (11) | 0.0461 (6) | |
O8 | 0.54446 (15) | 0.27471 (18) | 0.04963 (11) | 0.0441 (5) | |
Cl1 | 0.68388 (7) | 0.68768 (11) | 0.47414 (5) | 0.0732 (3) | |
Cl2 | 0.62100 (8) | 0.71621 (9) | 0.18265 (5) | 0.0690 (3) | |
Cl3 | 0.07311 (10) | 0.08467 (13) | −0.04885 (9) | 0.1168 (6) | |
Cl4 | 0.17694 (9) | 0.54153 (11) | 0.06876 (6) | 0.0899 (4) | |
S1 | 0.44404 (6) | 0.65578 (7) | 0.24313 (4) | 0.03951 (19) | |
S2 | 0.31731 (5) | 0.41072 (7) | 0.00093 (4) | 0.03802 (19) | |
Zn1 | 0.45325 (3) | 0.52527 (3) | 0.116433 (17) | 0.03809 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0483 (19) | 0.0283 (16) | 0.0476 (19) | −0.0001 (14) | 0.0150 (15) | −0.0068 (15) |
C2 | 0.0430 (18) | 0.0366 (18) | 0.054 (2) | 0.0020 (14) | 0.0149 (16) | −0.0062 (16) |
C3 | 0.052 (2) | 0.044 (2) | 0.051 (2) | 0.0089 (16) | 0.0104 (17) | −0.0064 (17) |
C4 | 0.0405 (19) | 0.043 (2) | 0.072 (3) | 0.0043 (16) | 0.0109 (18) | −0.0070 (19) |
C5 | 0.049 (2) | 0.039 (2) | 0.077 (3) | −0.0023 (16) | 0.0265 (19) | −0.0066 (19) |
C6 | 0.061 (2) | 0.0317 (17) | 0.054 (2) | −0.0056 (16) | 0.0260 (18) | −0.0063 (16) |
C7 | 0.0366 (16) | 0.0326 (16) | 0.0326 (15) | 0.0011 (13) | 0.0127 (13) | 0.0015 (13) |
C8 | 0.0351 (16) | 0.0368 (17) | 0.0328 (15) | −0.0030 (13) | 0.0101 (13) | −0.0013 (14) |
C9 | 0.0386 (17) | 0.0355 (17) | 0.0437 (17) | 0.0072 (14) | 0.0158 (14) | 0.0043 (15) |
C10 | 0.0437 (18) | 0.0388 (18) | 0.0346 (16) | 0.0035 (14) | 0.0108 (14) | 0.0083 (14) |
C11 | 0.0434 (18) | 0.045 (2) | 0.0407 (17) | 0.0015 (15) | 0.0048 (14) | 0.0002 (16) |
C12 | 0.048 (2) | 0.055 (2) | 0.048 (2) | 0.0158 (18) | 0.0000 (16) | −0.0009 (18) |
C13 | 0.072 (3) | 0.041 (2) | 0.060 (2) | 0.013 (2) | 0.013 (2) | 0.0081 (19) |
C14 | 0.061 (2) | 0.038 (2) | 0.073 (3) | −0.0053 (17) | 0.015 (2) | 0.0061 (19) |
C15 | 0.0412 (18) | 0.042 (2) | 0.058 (2) | −0.0020 (15) | 0.0092 (16) | 0.0106 (17) |
C16 | 0.0343 (16) | 0.050 (2) | 0.0336 (16) | 0.0065 (14) | 0.0068 (13) | 0.0073 (15) |
C17 | 0.0419 (19) | 0.052 (2) | 0.0443 (19) | −0.0029 (16) | 0.0073 (15) | 0.0061 (17) |
C18 | 0.048 (2) | 0.072 (3) | 0.070 (3) | −0.011 (2) | 0.004 (2) | 0.015 (2) |
C19 | 0.040 (2) | 0.122 (5) | 0.080 (3) | −0.009 (3) | 0.016 (2) | 0.019 (3) |
C20 | 0.043 (2) | 0.129 (5) | 0.065 (3) | 0.027 (3) | 0.022 (2) | 0.010 (3) |
C21 | 0.049 (2) | 0.073 (3) | 0.046 (2) | 0.0192 (19) | 0.0139 (16) | 0.0030 (19) |
C22 | 0.0346 (15) | 0.0334 (16) | 0.0321 (15) | −0.0023 (13) | 0.0083 (12) | 0.0006 (13) |
C23 | 0.0352 (16) | 0.0356 (17) | 0.0349 (16) | −0.0033 (13) | 0.0104 (13) | 0.0035 (14) |
C24 | 0.0367 (16) | 0.0393 (18) | 0.0327 (15) | −0.0031 (14) | 0.0102 (13) | 0.0008 (14) |
C25 | 0.0431 (18) | 0.0289 (16) | 0.0489 (19) | −0.0004 (14) | 0.0139 (15) | 0.0008 (15) |
C26 | 0.0486 (19) | 0.045 (2) | 0.052 (2) | 0.0025 (16) | 0.0163 (16) | −0.0065 (17) |
C27 | 0.060 (2) | 0.048 (2) | 0.083 (3) | 0.0109 (19) | 0.032 (2) | −0.007 (2) |
C28 | 0.052 (2) | 0.043 (2) | 0.097 (3) | 0.0128 (18) | 0.019 (2) | 0.010 (2) |
C29 | 0.067 (3) | 0.049 (2) | 0.065 (2) | 0.005 (2) | 0.009 (2) | 0.016 (2) |
C30 | 0.055 (2) | 0.043 (2) | 0.051 (2) | 0.0042 (17) | 0.0167 (17) | 0.0036 (17) |
C31 | 0.043 (2) | 0.056 (2) | 0.071 (2) | 0.0095 (17) | 0.0243 (18) | 0.012 (2) |
C32 | 0.067 (3) | 0.073 (3) | 0.069 (3) | 0.014 (2) | 0.041 (2) | 0.029 (2) |
C33 | 0.0418 (18) | 0.052 (2) | 0.0458 (18) | 0.0006 (16) | 0.0184 (15) | 0.0066 (17) |
C34 | 0.062 (2) | 0.046 (2) | 0.074 (3) | −0.0101 (18) | 0.034 (2) | 0.002 (2) |
N1 | 0.0462 (15) | 0.0300 (14) | 0.0340 (13) | −0.0019 (11) | 0.0133 (11) | 0.0005 (11) |
N2 | 0.0339 (13) | 0.0354 (15) | 0.0464 (15) | 0.0016 (11) | 0.0133 (12) | 0.0086 (12) |
N3 | 0.0370 (14) | 0.0426 (16) | 0.0515 (16) | 0.0043 (12) | 0.0215 (12) | 0.0135 (13) |
N4 | 0.0387 (14) | 0.0328 (14) | 0.0356 (13) | 0.0014 (11) | 0.0081 (11) | 0.0045 (12) |
N5 | 0.0389 (14) | 0.0349 (15) | 0.0462 (15) | 0.0005 (11) | 0.0206 (12) | 0.0058 (12) |
N6 | 0.0411 (14) | 0.0342 (15) | 0.0475 (15) | 0.0002 (12) | 0.0211 (12) | 0.0076 (12) |
O1 | 0.0611 (17) | 0.072 (2) | 0.080 (2) | −0.0129 (15) | 0.0329 (15) | −0.0137 (16) |
O2 | 0.156 (3) | 0.055 (2) | 0.062 (2) | −0.009 (2) | 0.033 (2) | 0.0071 (16) |
O3 | 0.0474 (13) | 0.0563 (15) | 0.0507 (13) | 0.0042 (11) | 0.0197 (11) | −0.0130 (12) |
O4 | 0.0726 (17) | 0.0336 (13) | 0.0566 (15) | 0.0086 (12) | 0.0109 (13) | 0.0037 (12) |
O5 | 0.0466 (13) | 0.0632 (16) | 0.0385 (12) | 0.0005 (12) | 0.0187 (10) | −0.0028 (12) |
O6 | 0.0624 (15) | 0.0448 (14) | 0.0498 (14) | −0.0028 (12) | 0.0074 (12) | 0.0156 (12) |
O7 | 0.0323 (12) | 0.0529 (15) | 0.0562 (14) | 0.0009 (10) | 0.0170 (10) | 0.0070 (12) |
O8 | 0.0415 (12) | 0.0425 (13) | 0.0549 (14) | −0.0006 (10) | 0.0244 (11) | 0.0090 (11) |
Cl1 | 0.0562 (6) | 0.1051 (9) | 0.0530 (6) | 0.0131 (6) | 0.0042 (4) | −0.0111 (6) |
Cl2 | 0.0884 (7) | 0.0679 (7) | 0.0600 (6) | −0.0338 (6) | 0.0361 (5) | −0.0118 (5) |
Cl3 | 0.0875 (9) | 0.0850 (10) | 0.1688 (15) | −0.0411 (8) | 0.0159 (9) | −0.0023 (10) |
Cl4 | 0.0998 (9) | 0.0860 (9) | 0.0894 (8) | 0.0301 (7) | 0.0343 (7) | −0.0232 (7) |
S1 | 0.0458 (4) | 0.0321 (4) | 0.0415 (4) | 0.0033 (3) | 0.0126 (3) | −0.0032 (3) |
S2 | 0.0391 (4) | 0.0404 (5) | 0.0346 (4) | −0.0002 (3) | 0.0096 (3) | 0.0048 (4) |
Zn1 | 0.0460 (2) | 0.0346 (2) | 0.0361 (2) | −0.00316 (17) | 0.01467 (16) | 0.00228 (16) |
C1—C2 | 1.382 (5) | C23—O8 | 1.243 (3) |
C1—C6 | 1.391 (5) | C23—N5 | 1.375 (4) |
C1—S1 | 1.809 (3) | C24—N6 | 1.377 (4) |
C2—C3 | 1.385 (5) | C24—C33 | 1.487 (4) |
C2—H2 | 0.9300 | C25—C30 | 1.375 (5) |
C3—C4 | 1.374 (5) | C25—C26 | 1.380 (5) |
C3—Cl1 | 1.741 (4) | C25—N5 | 1.423 (4) |
C4—C5 | 1.370 (5) | C26—C27 | 1.379 (5) |
C4—H4 | 0.9300 | C26—H26 | 0.9300 |
C5—C6 | 1.383 (5) | C27—C28 | 1.368 (6) |
C5—H5 | 0.9300 | C27—H27 | 0.9300 |
C6—Cl2 | 1.729 (4) | C28—C29 | 1.370 (6) |
C7—C9 | 1.348 (4) | C28—H28 | 0.9300 |
C7—N1 | 1.414 (4) | C29—C30 | 1.381 (5) |
C7—C8 | 1.452 (4) | C29—H29 | 0.9300 |
C8—O7 | 1.230 (3) | C30—H30 | 0.9300 |
C8—N2 | 1.390 (4) | C31—H31A | 0.9600 |
C9—N3 | 1.386 (4) | C31—H31B | 0.9600 |
C9—C31 | 1.492 (4) | C31—H31C | 0.9600 |
C10—C15 | 1.383 (5) | C32—N3 | 1.470 (4) |
C10—C11 | 1.384 (4) | C32—H32A | 0.9600 |
C10—N2 | 1.410 (4) | C32—H32B | 0.9600 |
C11—C12 | 1.379 (5) | C32—H32C | 0.9600 |
C11—H11 | 0.9300 | C33—H33A | 0.9600 |
C12—C13 | 1.370 (5) | C33—H33B | 0.9600 |
C12—H12 | 0.9300 | C33—H33C | 0.9600 |
C13—C14 | 1.375 (5) | C34—N6 | 1.462 (4) |
C13—H13 | 0.9300 | C34—H34A | 0.9600 |
C14—C15 | 1.380 (5) | C34—H34B | 0.9600 |
C14—H14 | 0.9300 | C34—H34C | 0.9600 |
C15—H15 | 0.9300 | N1—S1 | 1.592 (3) |
C16—C17 | 1.382 (5) | N1—Zn1 | 2.024 (2) |
C16—C21 | 1.386 (5) | N2—N3 | 1.417 (3) |
C16—S2 | 1.781 (3) | N4—S2 | 1.592 (3) |
C17—C18 | 1.369 (5) | N4—Zn1 | 2.031 (3) |
C17—H17 | 0.9300 | N5—N6 | 1.405 (3) |
C18—C19 | 1.362 (7) | O1—Zn1 | 2.028 (3) |
C18—Cl3 | 1.750 (5) | O1—H11O | 0.884 (18) |
C19—C20 | 1.367 (7) | O1—H12O | 0.896 (18) |
C19—H19 | 0.9300 | O2—Zn1 | 2.004 (3) |
C20—C21 | 1.384 (6) | O2—H21O | 0.883 (19) |
C20—H20 | 0.9300 | O2—H22O | 0.881 (19) |
C21—Cl4 | 1.729 (4) | O3—S1 | 1.437 (2) |
C22—C24 | 1.358 (4) | O4—S1 | 1.433 (2) |
C22—N4 | 1.422 (4) | O5—S2 | 1.433 (2) |
C22—C23 | 1.440 (4) | O6—S2 | 1.430 (3) |
C2—C1—C6 | 118.5 (3) | C28—C27—C26 | 120.6 (4) |
C2—C1—S1 | 117.2 (2) | C28—C27—H27 | 119.7 |
C6—C1—S1 | 124.3 (3) | C26—C27—H27 | 119.7 |
C1—C2—C3 | 119.8 (3) | C27—C28—C29 | 119.8 (4) |
C1—C2—H2 | 120.1 | C27—C28—H28 | 120.1 |
C3—C2—H2 | 120.1 | C29—C28—H28 | 120.1 |
C4—C3—C2 | 121.6 (3) | C28—C29—C30 | 120.8 (4) |
C4—C3—Cl1 | 118.6 (3) | C28—C29—H29 | 119.6 |
C2—C3—Cl1 | 119.8 (3) | C30—C29—H29 | 119.6 |
C5—C4—C3 | 118.7 (3) | C25—C30—C29 | 118.9 (3) |
C5—C4—H4 | 120.6 | C25—C30—H30 | 120.6 |
C3—C4—H4 | 120.6 | C29—C30—H30 | 120.6 |
C4—C5—C6 | 120.6 (3) | C9—C31—H31A | 109.5 |
C4—C5—H5 | 119.7 | C9—C31—H31B | 109.5 |
C6—C5—H5 | 119.7 | H31A—C31—H31B | 109.5 |
C5—C6—C1 | 120.8 (3) | C9—C31—H31C | 109.5 |
C5—C6—Cl2 | 116.6 (3) | H31A—C31—H31C | 109.5 |
C1—C6—Cl2 | 122.6 (3) | H31B—C31—H31C | 109.5 |
C9—C7—N1 | 127.9 (3) | N3—C32—H32A | 109.5 |
C9—C7—C8 | 107.8 (3) | N3—C32—H32B | 109.5 |
N1—C7—C8 | 124.0 (3) | H32A—C32—H32B | 109.5 |
O7—C8—N2 | 124.6 (3) | N3—C32—H32C | 109.5 |
O7—C8—C7 | 130.3 (3) | H32A—C32—H32C | 109.5 |
N2—C8—C7 | 105.0 (2) | H32B—C32—H32C | 109.5 |
C7—C9—N3 | 111.3 (3) | C24—C33—H33A | 109.5 |
C7—C9—C31 | 129.8 (3) | C24—C33—H33B | 109.5 |
N3—C9—C31 | 118.8 (3) | H33A—C33—H33B | 109.5 |
C15—C10—C11 | 119.7 (3) | C24—C33—H33C | 109.5 |
C15—C10—N2 | 121.0 (3) | H33A—C33—H33C | 109.5 |
C11—C10—N2 | 119.3 (3) | H33B—C33—H33C | 109.5 |
C12—C11—C10 | 119.5 (3) | N6—C34—H34A | 109.5 |
C12—C11—H11 | 120.3 | N6—C34—H34B | 109.5 |
C10—C11—H11 | 120.3 | H34A—C34—H34B | 109.5 |
C13—C12—C11 | 120.7 (3) | N6—C34—H34C | 109.5 |
C13—C12—H12 | 119.7 | H34A—C34—H34C | 109.5 |
C11—C12—H12 | 119.7 | H34B—C34—H34C | 109.5 |
C12—C13—C14 | 120.2 (4) | C7—N1—S1 | 116.0 (2) |
C12—C13—H13 | 119.9 | C7—N1—Zn1 | 117.49 (19) |
C14—C13—H13 | 119.9 | S1—N1—Zn1 | 126.19 (14) |
C13—C14—C15 | 119.7 (4) | C8—N2—C10 | 126.7 (3) |
C13—C14—H14 | 120.2 | C8—N2—N3 | 110.0 (2) |
C15—C14—H14 | 120.2 | C10—N2—N3 | 118.7 (2) |
C14—C15—C10 | 120.3 (3) | C9—N3—N2 | 105.4 (2) |
C14—C15—H15 | 119.8 | C9—N3—C32 | 117.7 (3) |
C10—C15—H15 | 119.8 | N2—N3—C32 | 114.7 (3) |
C17—C16—C21 | 118.8 (3) | C22—N4—S2 | 112.7 (2) |
C17—C16—S2 | 117.0 (2) | C22—N4—Zn1 | 122.10 (19) |
C21—C16—S2 | 124.1 (3) | S2—N4—Zn1 | 120.23 (14) |
C18—C17—C16 | 120.1 (4) | C23—N5—N6 | 109.3 (2) |
C18—C17—H17 | 120.0 | C23—N5—C25 | 123.6 (2) |
C16—C17—H17 | 120.0 | N6—N5—C25 | 120.0 (2) |
C19—C18—C17 | 121.1 (4) | C24—N6—N5 | 106.4 (2) |
C19—C18—Cl3 | 120.5 (4) | C24—N6—C34 | 122.6 (3) |
C17—C18—Cl3 | 118.4 (4) | N5—N6—C34 | 114.4 (3) |
C18—C19—C20 | 119.7 (4) | Zn1—O1—H11O | 120 (3) |
C18—C19—H19 | 120.1 | Zn1—O1—H12O | 108 (3) |
C20—C19—H19 | 120.1 | H11O—O1—H12O | 102 (2) |
C19—C20—C21 | 120.0 (4) | Zn1—O2—H21O | 110 (3) |
C19—C20—H20 | 120.0 | Zn1—O2—H22O | 126 (4) |
C21—C20—H20 | 120.0 | H21O—O2—H22O | 103 (3) |
C20—C21—C16 | 120.2 (4) | O4—S1—O3 | 117.03 (15) |
C20—C21—Cl4 | 118.1 (3) | O4—S1—N1 | 108.11 (14) |
C16—C21—Cl4 | 121.6 (3) | O3—S1—N1 | 112.20 (14) |
C24—C22—N4 | 128.6 (3) | O4—S1—C1 | 106.15 (16) |
C24—C22—C23 | 107.6 (3) | O3—S1—C1 | 103.70 (15) |
N4—C22—C23 | 123.8 (3) | N1—S1—C1 | 109.20 (14) |
O8—C23—N5 | 123.1 (3) | O6—S2—O5 | 116.33 (15) |
O8—C23—C22 | 131.0 (3) | O6—S2—N4 | 109.16 (14) |
N5—C23—C22 | 105.9 (2) | O5—S2—N4 | 113.04 (14) |
C22—C24—N6 | 110.0 (3) | O6—S2—C16 | 107.99 (15) |
C22—C24—C33 | 129.9 (3) | O5—S2—C16 | 104.64 (15) |
N6—C24—C33 | 120.1 (3) | N4—S2—C16 | 104.83 (14) |
C30—C25—C26 | 120.9 (3) | O2—Zn1—N1 | 108.83 (12) |
C30—C25—N5 | 121.0 (3) | O2—Zn1—O1 | 114.56 (15) |
C26—C25—N5 | 118.0 (3) | N1—Zn1—O1 | 105.49 (11) |
C27—C26—C25 | 119.1 (4) | O2—Zn1—N4 | 114.00 (13) |
C27—C26—H26 | 120.4 | N1—Zn1—N4 | 112.12 (10) |
C25—C26—H26 | 120.4 | O1—Zn1—N4 | 101.44 (11) |
C6—C1—C2—C3 | 1.3 (5) | C11—C10—N2—C8 | 47.2 (5) |
S1—C1—C2—C3 | −175.7 (3) | C15—C10—N2—N3 | 19.4 (4) |
C1—C2—C3—C4 | 0.8 (5) | C11—C10—N2—N3 | −159.5 (3) |
C1—C2—C3—Cl1 | −179.6 (3) | C7—C9—N3—N2 | 3.9 (4) |
C2—C3—C4—C5 | −2.0 (5) | C31—C9—N3—N2 | −178.1 (3) |
Cl1—C3—C4—C5 | 178.4 (3) | C7—C9—N3—C32 | 133.2 (3) |
C3—C4—C5—C6 | 1.2 (5) | C31—C9—N3—C32 | −48.8 (5) |
C4—C5—C6—C1 | 0.9 (5) | C8—N2—N3—C9 | −6.6 (3) |
C4—C5—C6—Cl2 | −179.0 (3) | C10—N2—N3—C9 | −164.0 (3) |
C2—C1—C6—C5 | −2.1 (5) | C8—N2—N3—C32 | −137.7 (3) |
S1—C1—C6—C5 | 174.7 (3) | C10—N2—N3—C32 | 65.0 (4) |
C2—C1—C6—Cl2 | 177.8 (3) | C24—C22—N4—S2 | −96.7 (3) |
S1—C1—C6—Cl2 | −5.4 (4) | C23—C22—N4—S2 | 85.3 (3) |
C9—C7—C8—O7 | 172.7 (3) | C24—C22—N4—Zn1 | 108.1 (3) |
N1—C7—C8—O7 | −2.0 (5) | C23—C22—N4—Zn1 | −69.8 (3) |
C9—C7—C8—N2 | −4.2 (3) | O8—C23—N5—N6 | 170.1 (3) |
N1—C7—C8—N2 | −178.8 (3) | C22—C23—N5—N6 | −7.3 (3) |
N1—C7—C9—N3 | 174.5 (3) | O8—C23—N5—C25 | 19.9 (5) |
C8—C7—C9—N3 | 0.1 (4) | C22—C23—N5—C25 | −157.6 (3) |
N1—C7—C9—C31 | −3.2 (6) | C30—C25—N5—C23 | 109.5 (4) |
C8—C7—C9—C31 | −177.7 (3) | C26—C25—N5—C23 | −67.0 (4) |
C15—C10—C11—C12 | −0.7 (5) | C30—C25—N5—N6 | −37.8 (4) |
N2—C10—C11—C12 | 178.3 (3) | C26—C25—N5—N6 | 145.8 (3) |
C10—C11—C12—C13 | −0.5 (5) | C22—C24—N6—N5 | −8.0 (3) |
C11—C12—C13—C14 | 1.6 (6) | C33—C24—N6—N5 | 172.4 (3) |
C12—C13—C14—C15 | −1.4 (6) | C22—C24—N6—C34 | −142.5 (3) |
C13—C14—C15—C10 | 0.2 (6) | C33—C24—N6—C34 | 38.0 (4) |
C11—C10—C15—C14 | 0.9 (5) | C23—N5—N6—C24 | 9.5 (3) |
N2—C10—C15—C14 | −178.1 (3) | C25—N5—N6—C24 | 161.0 (3) |
C21—C16—C17—C18 | 0.5 (5) | C23—N5—N6—C34 | 148.1 (3) |
S2—C16—C17—C18 | 176.4 (3) | C25—N5—N6—C34 | −60.4 (4) |
C16—C17—C18—C19 | 0.9 (6) | C7—N1—S1—O4 | −164.9 (2) |
C16—C17—C18—Cl3 | −178.7 (3) | Zn1—N1—S1—O4 | 21.9 (2) |
C17—C18—C19—C20 | −1.1 (7) | C7—N1—S1—O3 | −34.3 (3) |
Cl3—C18—C19—C20 | 178.4 (4) | Zn1—N1—S1—O3 | 152.46 (17) |
C18—C19—C20—C21 | −0.1 (7) | C7—N1—S1—C1 | 80.1 (2) |
C19—C20—C21—C16 | 1.5 (6) | Zn1—N1—S1—C1 | −93.1 (2) |
C19—C20—C21—Cl4 | −176.6 (4) | C2—C1—S1—O4 | 133.1 (3) |
C17—C16—C21—C20 | −1.6 (5) | C6—C1—S1—O4 | −43.7 (3) |
S2—C16—C21—C20 | −177.2 (3) | C2—C1—S1—O3 | 9.2 (3) |
C17—C16—C21—Cl4 | 176.3 (3) | C6—C1—S1—O3 | −167.6 (3) |
S2—C16—C21—Cl4 | 0.8 (4) | C2—C1—S1—N1 | −110.6 (3) |
C24—C22—C23—O8 | −174.8 (3) | C6—C1—S1—N1 | 72.6 (3) |
N4—C22—C23—O8 | 3.5 (5) | C22—N4—S2—O6 | −168.7 (2) |
C24—C22—C23—N5 | 2.3 (3) | Zn1—N4—S2—O6 | −13.0 (2) |
N4—C22—C23—N5 | −179.4 (3) | C22—N4—S2—O5 | −37.5 (2) |
N4—C22—C24—N6 | −174.6 (3) | Zn1—N4—S2—O5 | 118.13 (17) |
C23—C22—C24—N6 | 3.6 (3) | C22—N4—S2—C16 | 75.8 (2) |
N4—C22—C24—C33 | 5.0 (5) | Zn1—N4—S2—C16 | −128.50 (17) |
C23—C22—C24—C33 | −176.9 (3) | C17—C16—S2—O6 | 139.8 (2) |
C30—C25—C26—C27 | −1.1 (5) | C21—C16—S2—O6 | −44.6 (3) |
N5—C25—C26—C27 | 175.3 (3) | C17—C16—S2—O5 | 15.3 (3) |
C25—C26—C27—C28 | 0.5 (6) | C21—C16—S2—O5 | −169.1 (3) |
C26—C27—C28—C29 | 0.7 (6) | C17—C16—S2—N4 | −103.9 (3) |
C27—C28—C29—C30 | −1.3 (6) | C21—C16—S2—N4 | 71.7 (3) |
C26—C25—C30—C29 | 0.5 (5) | C7—N1—Zn1—O2 | 165.5 (2) |
N5—C25—C30—C29 | −175.8 (3) | S1—N1—Zn1—O2 | −21.4 (2) |
C28—C29—C30—C25 | 0.7 (6) | C7—N1—Zn1—O1 | −71.1 (2) |
C9—C7—N1—S1 | 76.1 (4) | S1—N1—Zn1—O1 | 101.98 (19) |
C8—C7—N1—S1 | −110.3 (3) | C7—N1—Zn1—N4 | 38.4 (2) |
C9—C7—N1—Zn1 | −110.1 (3) | S1—N1—Zn1—N4 | −148.45 (17) |
C8—C7—N1—Zn1 | 63.5 (3) | C22—N4—Zn1—O2 | 163.1 (2) |
O7—C8—N2—C10 | −15.3 (5) | S2—N4—Zn1—O2 | 9.8 (2) |
C7—C8—N2—C10 | 161.8 (3) | C22—N4—Zn1—N1 | −72.6 (2) |
O7—C8—N2—N3 | −170.4 (3) | S2—N4—Zn1—N1 | 134.01 (15) |
C7—C8—N2—N3 | 6.6 (3) | C22—N4—Zn1—O1 | 39.5 (2) |
C15—C10—N2—C8 | −133.8 (3) | S2—N4—Zn1—O1 | −113.89 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11O···O5i | 0.88 (2) | 2.52 (3) | 3.277 (4) | 145 (4) |
O1—H12O···O8 | 0.90 (2) | 2.06 (2) | 2.914 (4) | 160 (4) |
O2—H21O···O4 | 0.88 (2) | 2.22 (3) | 2.928 (4) | 137 (4) |
O2—H22O···O8i | 0.88 (2) | 2.05 (3) | 2.868 (4) | 154 (5) |
Symmetry code: (i) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C17H14Cl2N3O3S)2(H2O)2] |
Mr | 923.95 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 299 |
a, b, c (Å) | 15.0683 (7), 12.3009 (5), 21.8256 (9) |
β (°) | 104.681 (4) |
V (Å3) | 3913.4 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.07 |
Crystal size (mm) | 0.50 × 0.42 × 0.36 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector |
Absorption correction | Multi-scan (CrysAlis RED; Oxford Diffraction, 2007) |
Tmin, Tmax | 0.597, 0.698 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 29052, 7987, 5392 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.118, 1.09 |
No. of reflections | 7987 |
No. of parameters | 512 |
No. of restraints | 6 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.73, −0.56 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
N1—Zn1 | 2.024 (2) | O1—Zn1 | 2.028 (3) |
N4—Zn1 | 2.031 (3) | O2—Zn1 | 2.004 (3) |
O2—Zn1—N1 | 108.83 (12) | O2—Zn1—N4 | 114.00 (13) |
O2—Zn1—O1 | 114.56 (15) | N1—Zn1—N4 | 112.12 (10) |
N1—Zn1—O1 | 105.49 (11) | O1—Zn1—N4 | 101.44 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H11O···O5i | 0.884 (18) | 2.52 (3) | 3.277 (4) | 145 (4) |
O1—H12O···O8 | 0.896 (18) | 2.06 (2) | 2.914 (4) | 160 (4) |
O2—H21O···O4 | 0.883 (19) | 2.22 (3) | 2.928 (4) | 137 (4) |
O2—H22O···O8i | 0.881 (19) | 2.05 (3) | 2.868 (4) | 154 (5) |
Symmetry code: (i) −x+1, −y+1, −z. |
The interest to develop the coordination chemistry of pyrazolone derivatives is because of their biological and medicinal properties. They present a variety of biological activities ranging from anti-tumour, fungicide, bactericide, antiinflamatory and anti-viral activities (Prasad and Agarwal, 2007; Hernández-Delgadillo et al., 2006; Raman et al., 2003; Burdulene et al., 1999). As part of our efforts to investigate transition metal (II) complexes based on 4-aminoantypirine derivatives and sulfonamide pharmacophoric group, we describe the X-ray characterization of the title compound, (I).
The ZnII ion has a tetrahedral coordination formed by the two sulfonamide N atoms and the two water molecules (Table 1). The bond angles around the central Zn atom are close to the 109° angle of an ideal tetrahedral value. Both hydrogen atoms of each water molecule are involved in an intermolecular O—H···O [O—H···O = 2.52 (3) Å, O—H···O = 2.05 (3) Å, respectively] and an intramolecular O—H···O [O—H···O = 2.06 (2) Å, O—H···O = 2.22 (3) Å, respectively] hydrogen bonds (Table 2).