metal-organic compounds
The title compound, [Zn2(C15H12N2O2)2(C2H6OS)2], is a centrosymmetric dimer via a Zn—O bridge of 2.0038 (13) Å, with a ZnZn separation of 3.1370 (13) Å. The geometry of the five-coordinate environment of the Zn atoms is close to trigonal bipyramidal.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016118/cv6208sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016118/cv6208Isup2.hkl |
CCDC reference: 221651
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Bis{µ-N-[1-(2-
oxidophenyl)ethylidene]benzohydrazido}bis[(dimethylsulfoxido)zinc(II)] top
Crystal data top
[Zn2(C15H12N2O2)2(C2H6OS)2] | Z = 1 |
Mr = 791.53 | F(000) = 408 |
Triclinic, P1 | Dx = 1.564 Mg m−3 |
a = 7.690 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.214 (6) Å | Cell parameters from 8764 reflections |
c = 11.643 (6) Å | θ = 1.7–27.5° |
α = 98.479 (13)° | µ = 1.60 mm−1 |
β = 94.262 (12)° | T = 293 K |
γ = 110.338 (13)° | Block, pale yellow |
V = 840.3 (8) Å3 | 0.54 × 0.48 × 0.33 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3804 independent reflections |
Radiation source: fine-focus sealed tube | 3653 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.5°, θmin = 1.7° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −13→13 |
Tmin = 0.454, Tmax = 0.588 | l = −15→15 |
10556 measured reflections |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.024 | H-atom parameters constrained |
wR(F2) = 0.068 | w = 1/[σ2(Fo2) + (0.0374P)2 + 0.2073P] where P = (Fo2 + 2Fc2)/3 |
S = 1.10 | (Δ/σ)max < 0.001 |
3804 reflections | Δρmax = 0.27 e Å−3 |
221 parameters | Δρmin = −0.31 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0148 (15) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.14613 (2) | 0.136649 (15) | 0.580740 (13) | 0.03043 (8) | |
O1 | 0.04398 (15) | 0.05128 (11) | 0.40604 (9) | 0.0337 (2) | |
O2 | 0.1765 (2) | 0.26529 (12) | 0.73532 (10) | 0.0450 (3) | |
O3 | 0.39014 (17) | 0.10438 (14) | 0.59157 (12) | 0.0474 (3) | |
S1 | 0.47569 (6) | 0.03285 (5) | 0.67222 (5) | 0.04877 (12) | |
N1 | 0.19441 (18) | 0.32797 (12) | 0.52931 (11) | 0.0313 (2) | |
N2 | 0.20450 (19) | 0.43653 (13) | 0.62061 (11) | 0.0349 (3) | |
C1 | 0.12854 (19) | 0.10700 (15) | 0.31867 (12) | 0.0284 (3) | |
C2 | 0.1213 (2) | 0.01710 (16) | 0.21375 (13) | 0.0353 (3) | |
H2 | 0.0531 | −0.0797 | 0.2050 | 0.042* | |
C3 | 0.2129 (3) | 0.06852 (18) | 0.12297 (14) | 0.0403 (3) | |
H3 | 0.2049 | 0.0066 | 0.0540 | 0.048* | |
C4 | 0.3163 (2) | 0.21148 (19) | 0.13437 (14) | 0.0417 (4) | |
H4 | 0.3832 | 0.2460 | 0.0750 | 0.050* | |
C5 | 0.3189 (2) | 0.30231 (17) | 0.23475 (14) | 0.0371 (3) | |
H5 | 0.3869 | 0.3988 | 0.2411 | 0.045* | |
C6 | 0.2237 (2) | 0.25588 (15) | 0.32816 (12) | 0.0292 (3) | |
C7 | 0.2284 (2) | 0.36361 (14) | 0.42882 (13) | 0.0306 (3) | |
C8 | 0.2737 (3) | 0.51533 (16) | 0.41435 (15) | 0.0439 (4) | |
H8A | 0.1941 | 0.5542 | 0.4558 | 0.066* | |
H8B | 0.2537 | 0.5188 | 0.3327 | 0.066* | |
H8C | 0.4021 | 0.5699 | 0.4453 | 0.066* | |
C9 | 0.1922 (2) | 0.39056 (15) | 0.71993 (13) | 0.0317 (3) | |
C10 | 0.1986 (2) | 0.49549 (15) | 0.82521 (13) | 0.0322 (3) | |
C11 | 0.1421 (2) | 0.60873 (16) | 0.81514 (14) | 0.0382 (3) | |
H11 | 0.1049 | 0.6223 | 0.7413 | 0.046* | |
C12 | 0.1404 (3) | 0.70174 (18) | 0.91395 (17) | 0.0468 (4) | |
H12 | 0.0993 | 0.7760 | 0.9064 | 0.056* | |
C13 | 0.1995 (3) | 0.68450 (19) | 1.02362 (16) | 0.0487 (4) | |
H13 | 0.1984 | 0.7470 | 1.0901 | 0.058* | |
C14 | 0.2602 (3) | 0.5742 (2) | 1.03419 (16) | 0.0496 (4) | |
H14 | 0.3032 | 0.5637 | 1.1078 | 0.060* | |
C15 | 0.2576 (3) | 0.47891 (18) | 0.93562 (15) | 0.0416 (4) | |
H15 | 0.2956 | 0.4033 | 0.9436 | 0.050* | |
C16 | 0.3582 (4) | −0.1511 (2) | 0.6226 (2) | 0.0628 (6) | |
H16A | 0.2254 | −0.1729 | 0.6143 | 0.094* | |
H16B | 0.3914 | −0.2019 | 0.6782 | 0.094* | |
H16C | 0.3936 | −0.1788 | 0.5481 | 0.094* | |
C17 | 0.3808 (3) | 0.0488 (3) | 0.80627 (18) | 0.0621 (5) | |
H17A | 0.4184 | 0.1474 | 0.8410 | 0.093* | |
H17B | 0.4261 | 0.0004 | 0.8590 | 0.093* | |
H17C | 0.2467 | 0.0073 | 0.7911 | 0.093* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.03728 (11) | 0.02167 (10) | 0.02983 (11) | 0.00794 (7) | 0.00497 (7) | 0.00377 (6) |
O1 | 0.0407 (6) | 0.0247 (5) | 0.0287 (5) | 0.0027 (4) | 0.0097 (4) | 0.0041 (4) |
O2 | 0.0760 (9) | 0.0252 (5) | 0.0319 (5) | 0.0163 (5) | 0.0085 (5) | 0.0041 (4) |
O3 | 0.0424 (6) | 0.0499 (7) | 0.0594 (8) | 0.0213 (5) | 0.0147 (5) | 0.0241 (6) |
S1 | 0.0369 (2) | 0.0564 (3) | 0.0597 (3) | 0.02079 (19) | 0.00825 (18) | 0.0210 (2) |
N1 | 0.0380 (6) | 0.0246 (5) | 0.0298 (6) | 0.0103 (5) | 0.0052 (5) | 0.0025 (4) |
N2 | 0.0463 (7) | 0.0252 (6) | 0.0316 (6) | 0.0123 (5) | 0.0067 (5) | 0.0011 (5) |
C1 | 0.0288 (6) | 0.0283 (6) | 0.0280 (6) | 0.0097 (5) | 0.0054 (5) | 0.0061 (5) |
C2 | 0.0411 (8) | 0.0302 (7) | 0.0338 (7) | 0.0124 (6) | 0.0083 (6) | 0.0035 (6) |
C3 | 0.0521 (9) | 0.0421 (8) | 0.0302 (7) | 0.0211 (7) | 0.0116 (6) | 0.0045 (6) |
C4 | 0.0491 (9) | 0.0462 (9) | 0.0347 (8) | 0.0182 (7) | 0.0169 (7) | 0.0148 (7) |
C5 | 0.0419 (8) | 0.0342 (7) | 0.0363 (8) | 0.0114 (6) | 0.0107 (6) | 0.0129 (6) |
C6 | 0.0308 (6) | 0.0280 (7) | 0.0290 (6) | 0.0100 (5) | 0.0048 (5) | 0.0070 (5) |
C7 | 0.0324 (7) | 0.0247 (6) | 0.0323 (7) | 0.0076 (5) | 0.0028 (5) | 0.0057 (5) |
C8 | 0.0624 (11) | 0.0273 (7) | 0.0397 (8) | 0.0122 (7) | 0.0069 (7) | 0.0088 (6) |
C9 | 0.0340 (7) | 0.0243 (6) | 0.0330 (7) | 0.0071 (5) | 0.0049 (5) | 0.0019 (5) |
C10 | 0.0335 (7) | 0.0253 (6) | 0.0329 (7) | 0.0051 (5) | 0.0083 (5) | 0.0026 (5) |
C11 | 0.0436 (8) | 0.0312 (7) | 0.0383 (8) | 0.0125 (6) | 0.0070 (6) | 0.0038 (6) |
C12 | 0.0521 (10) | 0.0340 (8) | 0.0535 (10) | 0.0173 (7) | 0.0120 (8) | −0.0008 (7) |
C13 | 0.0544 (10) | 0.0408 (9) | 0.0420 (9) | 0.0116 (8) | 0.0137 (8) | −0.0086 (7) |
C14 | 0.0611 (11) | 0.0501 (10) | 0.0320 (8) | 0.0152 (8) | 0.0057 (7) | 0.0032 (7) |
C15 | 0.0520 (9) | 0.0349 (8) | 0.0370 (8) | 0.0154 (7) | 0.0056 (7) | 0.0052 (6) |
C16 | 0.0834 (15) | 0.0495 (11) | 0.0719 (14) | 0.0351 (11) | 0.0308 (12) | 0.0241 (10) |
C17 | 0.0633 (13) | 0.0793 (15) | 0.0472 (11) | 0.0308 (11) | 0.0017 (9) | 0.0129 (10) |
Geometric parameters (Å, º) top
Zn1—O1i | 2.0038 (13) | C5—H5 | 0.9300 |
Zn1—O2 | 2.0117 (14) | C6—C7 | 1.474 (2) |
Zn1—O3 | 2.0131 (16) | C7—C8 | 1.504 (2) |
Zn1—N1 | 2.0466 (16) | C8—H8A | 0.9600 |
Zn1—O1 | 2.0683 (15) | C8—H8B | 0.9600 |
Zn1—Zn1i | 3.1370 (13) | C8—H8C | 0.9600 |
O1—C1 | 1.3391 (17) | C9—C10 | 1.490 (2) |
O1—Zn1i | 2.0038 (13) | C10—C15 | 1.385 (2) |
O2—C9 | 1.2834 (19) | C10—C11 | 1.387 (2) |
O3—S1 | 1.5142 (14) | C11—C12 | 1.384 (2) |
S1—C16 | 1.761 (2) | C11—H11 | 0.9300 |
S1—C17 | 1.781 (2) | C12—C13 | 1.380 (3) |
N1—C7 | 1.294 (2) | C12—H12 | 0.9300 |
N1—N2 | 1.3949 (17) | C13—C14 | 1.379 (3) |
N2—C9 | 1.309 (2) | C13—H13 | 0.9300 |
C1—C2 | 1.401 (2) | C14—C15 | 1.385 (2) |
C1—C6 | 1.423 (2) | C14—H14 | 0.9300 |
C2—C3 | 1.381 (2) | C15—H15 | 0.9300 |
C2—H2 | 0.9300 | C16—H16A | 0.9600 |
C3—C4 | 1.379 (3) | C16—H16B | 0.9600 |
C3—H3 | 0.9300 | C16—H16C | 0.9600 |
C4—C5 | 1.375 (2) | C17—H17A | 0.9600 |
C4—H4 | 0.9300 | C17—H17B | 0.9600 |
C5—C6 | 1.405 (2) | C17—H17C | 0.9600 |
O2—Zn1—O1 | 155.78 (5) | C1—C6—C7 | 124.43 (13) |
O1i—Zn1—O2 | 105.70 (6) | N1—C7—C6 | 120.18 (13) |
O1i—Zn1—O3 | 103.94 (6) | N1—C7—C8 | 120.15 (13) |
O2—Zn1—O3 | 101.22 (6) | C6—C7—C8 | 119.68 (13) |
O1i—Zn1—N1 | 146.72 (5) | C7—C8—H8A | 109.5 |
O2—Zn1—N1 | 78.70 (6) | C7—C8—H8B | 109.5 |
O3—Zn1—N1 | 107.52 (5) | H8A—C8—H8B | 109.5 |
O1i—Zn1—O1 | 79.24 (5) | C7—C8—H8C | 109.5 |
O3—Zn1—O1 | 100.46 (5) | H8A—C8—H8C | 109.5 |
N1—Zn1—O1 | 84.59 (5) | H8B—C8—H8C | 109.5 |
O1i—Zn1—Zn1i | 40.37 (4) | O2—C9—N2 | 126.53 (13) |
O2—Zn1—Zn1i | 140.73 (4) | O2—C9—C10 | 117.31 (13) |
O3—Zn1—Zn1i | 105.88 (5) | N2—C9—C10 | 116.15 (13) |
N1—Zn1—Zn1i | 118.16 (5) | C15—C10—C11 | 118.91 (14) |
O1—Zn1—Zn1i | 38.87 (3) | C15—C10—C9 | 120.01 (14) |
C1—O1—Zn1i | 134.94 (9) | C11—C10—C9 | 121.06 (14) |
C1—O1—Zn1 | 122.63 (9) | C12—C11—C10 | 120.56 (16) |
Zn1i—O1—Zn1 | 100.76 (5) | C12—C11—H11 | 119.7 |
C9—O2—Zn1 | 110.64 (10) | C10—C11—H11 | 119.7 |
S1—O3—Zn1 | 132.71 (8) | C13—C12—C11 | 120.13 (17) |
O3—S1—C16 | 105.77 (11) | C13—C12—H12 | 119.9 |
O3—S1—C17 | 106.45 (10) | C11—C12—H12 | 119.9 |
C16—S1—C17 | 98.33 (12) | C14—C13—C12 | 119.66 (16) |
C7—N1—N2 | 116.66 (12) | C14—C13—H13 | 120.2 |
C7—N1—Zn1 | 129.87 (10) | C12—C13—H13 | 120.2 |
N2—N1—Zn1 | 113.29 (10) | C13—C14—C15 | 120.28 (17) |
C9—N2—N1 | 110.39 (12) | C13—C14—H14 | 119.9 |
O1—C1—C2 | 119.44 (13) | C15—C14—H14 | 119.9 |
O1—C1—C6 | 121.98 (12) | C10—C15—C14 | 120.43 (17) |
C2—C1—C6 | 118.57 (13) | C10—C15—H15 | 119.8 |
C3—C2—C1 | 121.68 (14) | C14—C15—H15 | 119.8 |
C3—C2—H2 | 119.2 | S1—C16—H16A | 109.5 |
C1—C2—H2 | 119.2 | S1—C16—H16B | 109.5 |
C4—C3—C2 | 120.16 (15) | H16A—C16—H16B | 109.5 |
C4—C3—H3 | 119.9 | S1—C16—H16C | 109.5 |
C2—C3—H3 | 119.9 | H16A—C16—H16C | 109.5 |
C5—C4—C3 | 119.03 (15) | H16B—C16—H16C | 109.5 |
C5—C4—H4 | 120.5 | S1—C17—H17A | 109.5 |
C3—C4—H4 | 120.5 | S1—C17—H17B | 109.5 |
C4—C5—C6 | 122.96 (15) | H17A—C17—H17B | 109.5 |
C4—C5—H5 | 118.5 | S1—C17—H17C | 109.5 |
C6—C5—H5 | 118.5 | H17A—C17—H17C | 109.5 |
C5—C6—C1 | 117.35 (13) | H17B—C17—H17C | 109.5 |
C5—C6—C7 | 118.22 (13) | ||
O1i—Zn1—O1—C1 | −167.26 (14) | Zn1—O1—C1—C6 | −34.09 (18) |
O2—Zn1—O1—C1 | 88.33 (16) | O1—C1—C2—C3 | −177.18 (15) |
O3—Zn1—O1—C1 | −64.89 (12) | C6—C1—C2—C3 | 3.8 (2) |
N1—Zn1—O1—C1 | 41.96 (11) | C1—C2—C3—C4 | 0.6 (3) |
Zn1i—Zn1—O1—C1 | −167.26 (14) | C2—C3—C4—C5 | −3.2 (3) |
O1i—Zn1—O1—Zn1i | 0.0 (1) | C3—C4—C5—C6 | 1.3 (3) |
O2—Zn1—O1—Zn1i | −104.41 (12) | C4—C5—C6—C1 | 3.0 (2) |
O3—Zn1—O1—Zn1i | 102.37 (6) | C4—C5—C6—C7 | −176.88 (15) |
N1—Zn1—O1—Zn1i | −150.78 (6) | O1—C1—C6—C5 | 175.57 (14) |
O1i—Zn1—O2—C9 | −140.38 (12) | C2—C1—C6—C5 | −5.5 (2) |
O3—Zn1—O2—C9 | 111.52 (12) | O1—C1—C6—C7 | −4.5 (2) |
N1—Zn1—O2—C9 | 5.66 (11) | C2—C1—C6—C7 | 174.44 (14) |
O1—Zn1—O2—C9 | −41.63 (19) | N2—N1—C7—C6 | 179.03 (12) |
Zn1i—Zn1—O2—C9 | −115.40 (11) | Zn1—N1—C7—C6 | 4.3 (2) |
O1i—Zn1—O3—S1 | −45.18 (12) | N2—N1—C7—C8 | −0.7 (2) |
O2—Zn1—O3—S1 | 64.30 (13) | Zn1—N1—C7—C8 | −175.49 (12) |
N1—Zn1—O3—S1 | 145.85 (11) | C5—C6—C7—N1 | −159.11 (14) |
O1—Zn1—O3—S1 | −126.56 (12) | C1—C6—C7—N1 | 21.0 (2) |
Zn1i—Zn1—O3—S1 | −86.98 (12) | C5—C6—C7—C8 | 20.7 (2) |
Zn1—O3—S1—C16 | 76.50 (14) | C1—C6—C7—C8 | −159.27 (15) |
Zn1—O3—S1—C17 | −27.41 (15) | Zn1—O2—C9—N2 | −5.8 (2) |
O1i—Zn1—N1—C7 | −89.04 (16) | Zn1—O2—C9—C10 | 174.65 (10) |
O2—Zn1—N1—C7 | 169.51 (15) | N1—N2—C9—O2 | 1.2 (2) |
O3—Zn1—N1—C7 | 71.18 (14) | N1—N2—C9—C10 | −179.26 (12) |
O1—Zn1—N1—C7 | −28.11 (14) | O2—C9—C10—C15 | 24.2 (2) |
Zn1i—Zn1—N1—C7 | −48.44 (15) | N2—C9—C10—C15 | −155.36 (15) |
O1i—Zn1—N1—N2 | 96.05 (12) | O2—C9—C10—C11 | −154.23 (15) |
O2—Zn1—N1—N2 | −5.39 (10) | N2—C9—C10—C11 | 26.2 (2) |
O3—Zn1—N1—N2 | −103.73 (10) | C15—C10—C11—C12 | −1.5 (2) |
O1—Zn1—N1—N2 | 156.98 (10) | C9—C10—C11—C12 | 176.98 (15) |
Zn1i—Zn1—N1—N2 | 136.65 (9) | C10—C11—C12—C13 | 1.6 (3) |
C7—N1—N2—C9 | −171.55 (14) | C11—C12—C13—C14 | 0.0 (3) |
Zn1—N1—N2—C9 | 4.08 (15) | C12—C13—C14—C15 | −1.6 (3) |
Zn1i—O1—C1—C2 | −15.2 (2) | C11—C10—C15—C14 | −0.1 (3) |
Zn1—O1—C1—C2 | 146.97 (11) | C9—C10—C15—C14 | −178.62 (16) |
Zn1i—O1—C1—C6 | 163.73 (11) | C13—C14—C15—C10 | 1.7 (3) |
Symmetry code: (i) −x, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O2i | 0.93 | 2.33 | 3.167 (3) | 149 |
C16—H16C···O3ii | 0.96 | 2.42 | 3.258 (4) | 145 |
Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1. |