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The title compound, [Zn2(C15H12N2O2)2(C2H6OS)2], is a centrosymmetric dimer via a Zn—O bridge of 2.0038 (13) Å, with a Zn...Zn separation of 3.1370 (13) Å. The geometry of the five-coordinate environment of the Zn atoms is close to trigonal bipyramidal.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803016118/cv6208sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803016118/cv6208Isup2.hkl
Contains datablock I

CCDC reference: 221651

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.024
  • wR factor = 0.068
  • Data-to-parameter ratio = 17.2

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








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 = 791.53F(000) = 408
Triclinic, P1Dx = 1.564 Mg m3
a = 7.690 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.214 (6) ÅCell parameters from 8764 reflections
c = 11.643 (6) Åθ = 1.7–27.5°
α = 98.479 (13)°µ = 1.60 mm1
β = 94.262 (12)°T = 293 K
γ = 110.338 (13)°Block, pale yellow
V = 840.3 (8) Å30.54 × 0.48 × 0.33 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
3804 independent reflections
Radiation source: fine-focus sealed tube3653 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.019
Detector resolution: 83.66 pixels mm-1θmax = 27.5°, θmin = 1.7°
ω scansh = 99
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1313
Tmin = 0.454, Tmax = 0.588l = 1515
10556 measured reflections
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)] = 0.024H-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 reflectionsΔρmax = 0.27 e Å3
221 parametersΔρmin = 0.31 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0148 (15)
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.14613 (2)0.136649 (15)0.580740 (13)0.03043 (8)
O10.04398 (15)0.05128 (11)0.40604 (9)0.0337 (2)
O20.1765 (2)0.26529 (12)0.73532 (10)0.0450 (3)
O30.39014 (17)0.10438 (14)0.59157 (12)0.0474 (3)
S10.47569 (6)0.03285 (5)0.67222 (5)0.04877 (12)
N10.19441 (18)0.32797 (12)0.52931 (11)0.0313 (2)
N20.20450 (19)0.43653 (13)0.62061 (11)0.0349 (3)
C10.12854 (19)0.10700 (15)0.31867 (12)0.0284 (3)
C20.1213 (2)0.01710 (16)0.21375 (13)0.0353 (3)
H20.05310.07970.20500.042*
C30.2129 (3)0.06852 (18)0.12297 (14)0.0403 (3)
H30.20490.00660.05400.048*
C40.3163 (2)0.21148 (19)0.13437 (14)0.0417 (4)
H40.38320.24600.07500.050*
C50.3189 (2)0.30231 (17)0.23475 (14)0.0371 (3)
H50.38690.39880.24110.045*
C60.2237 (2)0.25588 (15)0.32816 (12)0.0292 (3)
C70.2284 (2)0.36361 (14)0.42882 (13)0.0306 (3)
C80.2737 (3)0.51533 (16)0.41435 (15)0.0439 (4)
H8A0.19410.55420.45580.066*
H8B0.25370.51880.33270.066*
H8C0.40210.56990.44530.066*
C90.1922 (2)0.39056 (15)0.71993 (13)0.0317 (3)
C100.1986 (2)0.49549 (15)0.82521 (13)0.0322 (3)
C110.1421 (2)0.60873 (16)0.81514 (14)0.0382 (3)
H110.10490.62230.74130.046*
C120.1404 (3)0.70174 (18)0.91395 (17)0.0468 (4)
H120.09930.77600.90640.056*
C130.1995 (3)0.68450 (19)1.02362 (16)0.0487 (4)
H130.19840.74701.09010.058*
C140.2602 (3)0.5742 (2)1.03419 (16)0.0496 (4)
H140.30320.56371.10780.060*
C150.2576 (3)0.47891 (18)0.93562 (15)0.0416 (4)
H150.29560.40330.94360.050*
C160.3582 (4)0.1511 (2)0.6226 (2)0.0628 (6)
H16A0.22540.17290.61430.094*
H16B0.39140.20190.67820.094*
H16C0.39360.17880.54810.094*
C170.3808 (3)0.0488 (3)0.80627 (18)0.0621 (5)
H17A0.41840.14740.84100.093*
H17B0.42610.00040.85900.093*
H17C0.24670.00730.79110.093*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.03728 (11)0.02167 (10)0.02983 (11)0.00794 (7)0.00497 (7)0.00377 (6)
O10.0407 (6)0.0247 (5)0.0287 (5)0.0027 (4)0.0097 (4)0.0041 (4)
O20.0760 (9)0.0252 (5)0.0319 (5)0.0163 (5)0.0085 (5)0.0041 (4)
O30.0424 (6)0.0499 (7)0.0594 (8)0.0213 (5)0.0147 (5)0.0241 (6)
S10.0369 (2)0.0564 (3)0.0597 (3)0.02079 (19)0.00825 (18)0.0210 (2)
N10.0380 (6)0.0246 (5)0.0298 (6)0.0103 (5)0.0052 (5)0.0025 (4)
N20.0463 (7)0.0252 (6)0.0316 (6)0.0123 (5)0.0067 (5)0.0011 (5)
C10.0288 (6)0.0283 (6)0.0280 (6)0.0097 (5)0.0054 (5)0.0061 (5)
C20.0411 (8)0.0302 (7)0.0338 (7)0.0124 (6)0.0083 (6)0.0035 (6)
C30.0521 (9)0.0421 (8)0.0302 (7)0.0211 (7)0.0116 (6)0.0045 (6)
C40.0491 (9)0.0462 (9)0.0347 (8)0.0182 (7)0.0169 (7)0.0148 (7)
C50.0419 (8)0.0342 (7)0.0363 (8)0.0114 (6)0.0107 (6)0.0129 (6)
C60.0308 (6)0.0280 (7)0.0290 (6)0.0100 (5)0.0048 (5)0.0070 (5)
C70.0324 (7)0.0247 (6)0.0323 (7)0.0076 (5)0.0028 (5)0.0057 (5)
C80.0624 (11)0.0273 (7)0.0397 (8)0.0122 (7)0.0069 (7)0.0088 (6)
C90.0340 (7)0.0243 (6)0.0330 (7)0.0071 (5)0.0049 (5)0.0019 (5)
C100.0335 (7)0.0253 (6)0.0329 (7)0.0051 (5)0.0083 (5)0.0026 (5)
C110.0436 (8)0.0312 (7)0.0383 (8)0.0125 (6)0.0070 (6)0.0038 (6)
C120.0521 (10)0.0340 (8)0.0535 (10)0.0173 (7)0.0120 (8)0.0008 (7)
C130.0544 (10)0.0408 (9)0.0420 (9)0.0116 (8)0.0137 (8)0.0086 (7)
C140.0611 (11)0.0501 (10)0.0320 (8)0.0152 (8)0.0057 (7)0.0032 (7)
C150.0520 (9)0.0349 (8)0.0370 (8)0.0154 (7)0.0056 (7)0.0052 (6)
C160.0834 (15)0.0495 (11)0.0719 (14)0.0351 (11)0.0308 (12)0.0241 (10)
C170.0633 (13)0.0793 (15)0.0472 (11)0.0308 (11)0.0017 (9)0.0129 (10)
Geometric parameters (Å, º) top
Zn1—O1i2.0038 (13)C5—H50.9300
Zn1—O22.0117 (14)C6—C71.474 (2)
Zn1—O32.0131 (16)C7—C81.504 (2)
Zn1—N12.0466 (16)C8—H8A0.9600
Zn1—O12.0683 (15)C8—H8B0.9600
Zn1—Zn1i3.1370 (13)C8—H8C0.9600
O1—C11.3391 (17)C9—C101.490 (2)
O1—Zn1i2.0038 (13)C10—C151.385 (2)
O2—C91.2834 (19)C10—C111.387 (2)
O3—S11.5142 (14)C11—C121.384 (2)
S1—C161.761 (2)C11—H110.9300
S1—C171.781 (2)C12—C131.380 (3)
N1—C71.294 (2)C12—H120.9300
N1—N21.3949 (17)C13—C141.379 (3)
N2—C91.309 (2)C13—H130.9300
C1—C21.401 (2)C14—C151.385 (2)
C1—C61.423 (2)C14—H140.9300
C2—C31.381 (2)C15—H150.9300
C2—H20.9300C16—H16A0.9600
C3—C41.379 (3)C16—H16B0.9600
C3—H30.9300C16—H16C0.9600
C4—C51.375 (2)C17—H17A0.9600
C4—H40.9300C17—H17B0.9600
C5—C61.405 (2)C17—H17C0.9600
O2—Zn1—O1155.78 (5)C1—C6—C7124.43 (13)
O1i—Zn1—O2105.70 (6)N1—C7—C6120.18 (13)
O1i—Zn1—O3103.94 (6)N1—C7—C8120.15 (13)
O2—Zn1—O3101.22 (6)C6—C7—C8119.68 (13)
O1i—Zn1—N1146.72 (5)C7—C8—H8A109.5
O2—Zn1—N178.70 (6)C7—C8—H8B109.5
O3—Zn1—N1107.52 (5)H8A—C8—H8B109.5
O1i—Zn1—O179.24 (5)C7—C8—H8C109.5
O3—Zn1—O1100.46 (5)H8A—C8—H8C109.5
N1—Zn1—O184.59 (5)H8B—C8—H8C109.5
O1i—Zn1—Zn1i40.37 (4)O2—C9—N2126.53 (13)
O2—Zn1—Zn1i140.73 (4)O2—C9—C10117.31 (13)
O3—Zn1—Zn1i105.88 (5)N2—C9—C10116.15 (13)
N1—Zn1—Zn1i118.16 (5)C15—C10—C11118.91 (14)
O1—Zn1—Zn1i38.87 (3)C15—C10—C9120.01 (14)
C1—O1—Zn1i134.94 (9)C11—C10—C9121.06 (14)
C1—O1—Zn1122.63 (9)C12—C11—C10120.56 (16)
Zn1i—O1—Zn1100.76 (5)C12—C11—H11119.7
C9—O2—Zn1110.64 (10)C10—C11—H11119.7
S1—O3—Zn1132.71 (8)C13—C12—C11120.13 (17)
O3—S1—C16105.77 (11)C13—C12—H12119.9
O3—S1—C17106.45 (10)C11—C12—H12119.9
C16—S1—C1798.33 (12)C14—C13—C12119.66 (16)
C7—N1—N2116.66 (12)C14—C13—H13120.2
C7—N1—Zn1129.87 (10)C12—C13—H13120.2
N2—N1—Zn1113.29 (10)C13—C14—C15120.28 (17)
C9—N2—N1110.39 (12)C13—C14—H14119.9
O1—C1—C2119.44 (13)C15—C14—H14119.9
O1—C1—C6121.98 (12)C10—C15—C14120.43 (17)
C2—C1—C6118.57 (13)C10—C15—H15119.8
C3—C2—C1121.68 (14)C14—C15—H15119.8
C3—C2—H2119.2S1—C16—H16A109.5
C1—C2—H2119.2S1—C16—H16B109.5
C4—C3—C2120.16 (15)H16A—C16—H16B109.5
C4—C3—H3119.9S1—C16—H16C109.5
C2—C3—H3119.9H16A—C16—H16C109.5
C5—C4—C3119.03 (15)H16B—C16—H16C109.5
C5—C4—H4120.5S1—C17—H17A109.5
C3—C4—H4120.5S1—C17—H17B109.5
C4—C5—C6122.96 (15)H17A—C17—H17B109.5
C4—C5—H5118.5S1—C17—H17C109.5
C6—C5—H5118.5H17A—C17—H17C109.5
C5—C6—C1117.35 (13)H17B—C17—H17C109.5
C5—C6—C7118.22 (13)
O1i—Zn1—O1—C1167.26 (14)Zn1—O1—C1—C634.09 (18)
O2—Zn1—O1—C188.33 (16)O1—C1—C2—C3177.18 (15)
O3—Zn1—O1—C164.89 (12)C6—C1—C2—C33.8 (2)
N1—Zn1—O1—C141.96 (11)C1—C2—C3—C40.6 (3)
Zn1i—Zn1—O1—C1167.26 (14)C2—C3—C4—C53.2 (3)
O1i—Zn1—O1—Zn1i0.0 (1)C3—C4—C5—C61.3 (3)
O2—Zn1—O1—Zn1i104.41 (12)C4—C5—C6—C13.0 (2)
O3—Zn1—O1—Zn1i102.37 (6)C4—C5—C6—C7176.88 (15)
N1—Zn1—O1—Zn1i150.78 (6)O1—C1—C6—C5175.57 (14)
O1i—Zn1—O2—C9140.38 (12)C2—C1—C6—C55.5 (2)
O3—Zn1—O2—C9111.52 (12)O1—C1—C6—C74.5 (2)
N1—Zn1—O2—C95.66 (11)C2—C1—C6—C7174.44 (14)
O1—Zn1—O2—C941.63 (19)N2—N1—C7—C6179.03 (12)
Zn1i—Zn1—O2—C9115.40 (11)Zn1—N1—C7—C64.3 (2)
O1i—Zn1—O3—S145.18 (12)N2—N1—C7—C80.7 (2)
O2—Zn1—O3—S164.30 (13)Zn1—N1—C7—C8175.49 (12)
N1—Zn1—O3—S1145.85 (11)C5—C6—C7—N1159.11 (14)
O1—Zn1—O3—S1126.56 (12)C1—C6—C7—N121.0 (2)
Zn1i—Zn1—O3—S186.98 (12)C5—C6—C7—C820.7 (2)
Zn1—O3—S1—C1676.50 (14)C1—C6—C7—C8159.27 (15)
Zn1—O3—S1—C1727.41 (15)Zn1—O2—C9—N25.8 (2)
O1i—Zn1—N1—C789.04 (16)Zn1—O2—C9—C10174.65 (10)
O2—Zn1—N1—C7169.51 (15)N1—N2—C9—O21.2 (2)
O3—Zn1—N1—C771.18 (14)N1—N2—C9—C10179.26 (12)
O1—Zn1—N1—C728.11 (14)O2—C9—C10—C1524.2 (2)
Zn1i—Zn1—N1—C748.44 (15)N2—C9—C10—C15155.36 (15)
O1i—Zn1—N1—N296.05 (12)O2—C9—C10—C11154.23 (15)
O2—Zn1—N1—N25.39 (10)N2—C9—C10—C1126.2 (2)
O3—Zn1—N1—N2103.73 (10)C15—C10—C11—C121.5 (2)
O1—Zn1—N1—N2156.98 (10)C9—C10—C11—C12176.98 (15)
Zn1i—Zn1—N1—N2136.65 (9)C10—C11—C12—C131.6 (3)
C7—N1—N2—C9171.55 (14)C11—C12—C13—C140.0 (3)
Zn1—N1—N2—C94.08 (15)C12—C13—C14—C151.6 (3)
Zn1i—O1—C1—C215.2 (2)C11—C10—C15—C140.1 (3)
Zn1—O1—C1—C2146.97 (11)C9—C10—C15—C14178.62 (16)
Zn1i—O1—C1—C6163.73 (11)C13—C14—C15—C101.7 (3)
Symmetry code: (i) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.333.167 (3)149
C16—H16C···O3ii0.962.423.258 (4)145
Symmetry codes: (i) x, y, z+1; (ii) x+1, y, z+1.
 

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