Bis{μ-N-[1-(2-oxido­phenyl)­ethyl­idene]­benzohydr­azido}bis­[(di­methyl­sulfoxide)­zinc(II)]

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.

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

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Computing details

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)]

Crystal data

[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) Å^3	0.54 × 0.48 × 0.33 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.024	H-atom parameters constrained
wR(F^2) = 0.068	w = 1/[σ^2(Fo^2) + (0.0374P)^2 + 0.2073P] where P = (Fo^2 + 2Fc^2)/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+0.001xFc^2λ^3/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Zn1—O1^i	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—Zn1^i	3.1370 (13)	C8—H8C	0.9600
O1—C1	1.3391 (17)	C9—C10	1.490 (2)
O1—Zn1^i	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)
O1^i—Zn1—O2	105.70 (6)	N1—C7—C6	120.18 (13)
O1^i—Zn1—O3	103.94 (6)	N1—C7—C8	120.15 (13)
O2—Zn1—O3	101.22 (6)	C6—C7—C8	119.68 (13)
O1^i—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
O1^i—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
O1^i—Zn1—Zn1^i	40.37 (4)	O2—C9—N2	126.53 (13)
O2—Zn1—Zn1^i	140.73 (4)	O2—C9—C10	117.31 (13)
O3—Zn1—Zn1^i	105.88 (5)	N2—C9—C10	116.15 (13)
N1—Zn1—Zn1^i	118.16 (5)	C15—C10—C11	118.91 (14)
O1—Zn1—Zn1^i	38.87 (3)	C15—C10—C9	120.01 (14)
C1—O1—Zn1^i	134.94 (9)	C11—C10—C9	121.06 (14)
C1—O1—Zn1	122.63 (9)	C12—C11—C10	120.56 (16)
Zn1^i—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)
O1^i—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)
Zn1^i—Zn1—O1—C1	−167.26 (14)	C2—C3—C4—C5	−3.2 (3)
O1^i—Zn1—O1—Zn1^i	0.0 (1)	C3—C4—C5—C6	1.3 (3)
O2—Zn1—O1—Zn1^i	−104.41 (12)	C4—C5—C6—C1	3.0 (2)
O3—Zn1—O1—Zn1^i	102.37 (6)	C4—C5—C6—C7	−176.88 (15)
N1—Zn1—O1—Zn1^i	−150.78 (6)	O1—C1—C6—C5	175.57 (14)
O1^i—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)
Zn1^i—Zn1—O2—C9	−115.40 (11)	Zn1—N1—C7—C6	4.3 (2)
O1^i—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)
Zn1^i—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)
O1^i—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)
Zn1^i—Zn1—N1—C7	−48.44 (15)	N2—C9—C10—C15	−155.36 (15)
O1^i—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)
Zn1^i—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)
Zn1^i—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)
Zn1^i—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)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O2^i	0.93	2.33	3.167 (3)	149
C16—H16C···O3^ii	0.96	2.42	3.258 (4)	145

Symmetry codes: (i) −x, −y, −z+1; (ii) −x+1, −y, −z+1.