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Acta Crystallogr Sect E Struct Rep Online. 2008 February 1; 64(Pt 2): m414.
Published online 2008 January 25. doi:  10.1107/S1600536808002201
PMCID: PMC2960193

Bis{μ-N′-[1-(5-bromo-2-oxidophen­yl)ethyl­idene]benzene­sulfono­hydrazidato}-κ3 O 2,N′:N3 N:O 2,N′-bis­[(dimethyl sulfoxide-κO)copper(II)]

Abstract

In the title centrosymmetric dinuclear complex, [Cu2(C15H11BrN2O3S)2(C2H6OS)2], the CuII ion is N,O-chelated by a dianionic ligand, monocoordinated by the sulfonamide N atom of a symmetry-related ligand and coordinated by an O atom from a dimethyl sulfoxide ligand, forming a distorted square-planar coordination geometry.

Related literature

For the structure of 2′-[1-(2-hydroxy­phen­yl)ethyl­idene]benzene­sulfonohydrazide, see: Ali et al. (2007 [triangle]).

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Object name is e-64-0m414-scheme1.jpg

Experimental

Crystal data

  • [Cu2(C15H11BrN2O3S)2(C2H6OS)2]
  • M r = 1017.77
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m414-efi1.jpg
  • a = 8.0831 (1) Å
  • b = 10.4972 (2) Å
  • c = 12.9481 (2) Å
  • α = 68.157 (1)°
  • β = 74.928 (1)°
  • γ = 70.691 (1)°
  • V = 950.56 (3) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 3.49 mm−1
  • T = 123 (2) K
  • 0.40 × 0.31 × 0.20 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.335, T max = 0.542 (expected range = 0.308–0.497)
  • 12330 measured reflections
  • 4318 independent reflections
  • 3788 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.151
  • S = 1.21
  • 4318 reflections
  • 238 parameters
  • H-atom parameters constrained
  • Δρmax = 1.75 e Å−3
  • Δρmin = −0.89 e Å−3

Data collection: APEX2 (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002201/lh2588sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002201/lh2588Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank the University of Canterbury, New Zealand, for the diffraction measurements, and the Science Fund (12–02-03–2031) and the Fundamental Research Grant Scheme (FP064/2006 A) for supporting this study.

supplementary crystallographic information

Experimental

The Schiff base ligand was synthesized by refluxing 5-bromo-2-hydroxyacetophenone (0.6 g, 2.8 mmol) with benzene sulfonohydrazide (0.48 g,2.8 mmol)in ethanol for 2 h. The ligand then was refluxed with Copper (II) acetate for 5 h. The brown crystal were obtained by recrystalization the product from DMSO.

Refinement

All H atoms were placed in calculated positions (C–H = 0.95–0.98 Å) and were included in the refinement in the riding-model approximation with Uiso(H) set to 1.2Ueq(C) or 1.5Ueq(C) for methyl H atoms.

Figures

Fig. 1.
The molecular structure with displacement ellipsoids drawn at the 50% probability level, and H atoms shown as spheres of arbitrary radii [symmetry code: (i) -x + 2, -y + 1, -z].

Crystal data

[Cu2(C15H11BrN2O3S)2(C2H6OS)2]Z = 1
Mr = 1017.77F(000) = 510
Triclinic, P1Dx = 1.778 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.0831 (1) ÅCell parameters from 7546 reflections
b = 10.4972 (2) Åθ = 2.7–31.0°
c = 12.9481 (2) ŵ = 3.49 mm1
α = 68.157 (1)°T = 123 K
β = 74.928 (1)°Block, green
γ = 70.691 (1)°0.40 × 0.31 × 0.20 mm
V = 950.56 (3) Å3

Data collection

Bruker APEXII diffractometer4318 independent reflections
Radiation source: medium-focus sealed tube3788 reflections with I > 2σ(I)
GraphiteRint = 0.027
[var phi] and ω scansθmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −10→10
Tmin = 0.335, Tmax = 0.542k = −13→13
12330 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.21w = 1/[σ2(Fo2) + (0.0827P)2 + 1.8365P] where P = (Fo2 + 2Fc2)/3
4318 reflections(Δ/σ)max = 0.001
238 parametersΔρmax = 1.75 e Å3
0 restraintsΔρmin = −0.89 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Br10.33316 (6)0.23924 (5)0.54963 (4)0.03789 (17)
Cu11.09563 (6)0.32031 (5)0.10740 (4)0.02020 (15)
S11.13219 (13)0.63204 (10)0.05283 (8)0.0213 (2)
S21.41379 (13)0.06832 (10)0.18255 (8)0.0230 (2)
O11.0528 (4)0.2167 (3)0.2622 (3)0.0285 (6)
O21.2628 (4)0.4956 (3)0.0677 (3)0.0278 (6)
O31.1615 (4)0.7489 (3)−0.0472 (3)0.0292 (7)
O41.3150 (4)0.1704 (3)0.0840 (2)0.0253 (6)
N10.9142 (4)0.4879 (3)0.1354 (3)0.0195 (6)
N20.9352 (4)0.6205 (3)0.0558 (3)0.0198 (6)
C10.8917 (5)0.2298 (4)0.3191 (3)0.0219 (8)
C20.8558 (6)0.1098 (5)0.4082 (3)0.0269 (9)
H20.94720.02360.42120.032*
C30.6946 (6)0.1120 (5)0.4770 (3)0.0274 (9)
H30.67590.02940.53700.033*
C40.5591 (6)0.2368 (5)0.4575 (3)0.0249 (8)
C50.5843 (5)0.3557 (4)0.3695 (4)0.0243 (8)
H50.48890.43930.35690.029*
C60.7481 (5)0.3565 (4)0.2975 (3)0.0208 (7)
C70.7691 (5)0.4889 (4)0.2075 (3)0.0217 (8)
C80.6221 (7)0.6230 (5)0.1999 (5)0.0392 (12)
H8A0.66310.70330.14280.059*
H8B0.58750.63960.27310.059*
H8C0.51980.61350.17880.059*
C101.1190 (5)0.6831 (4)0.1713 (3)0.0220 (8)
C111.1381 (6)0.5793 (5)0.2752 (4)0.0269 (8)
H111.15580.48220.28330.032*
C121.1307 (6)0.6200 (5)0.3673 (4)0.0318 (9)
H121.14180.55050.43930.038*
C131.1072 (6)0.7618 (5)0.3547 (4)0.0327 (10)
H131.10640.78840.41740.039*
C141.0849 (6)0.8649 (5)0.2507 (4)0.0304 (9)
H141.06560.96220.24290.036*
C151.0910 (6)0.8258 (4)0.1583 (4)0.0249 (8)
H151.07610.89570.08690.030*
C161.6285 (6)0.0005 (5)0.1132 (4)0.0294 (9)
H16A1.6190−0.05420.06900.044*
H16B1.7060−0.06130.16940.044*
H16C1.67860.07970.06310.044*
C171.4719 (6)0.1775 (5)0.2371 (4)0.0310 (9)
H17A1.36690.22150.28230.046*
H17B1.51680.25190.17460.046*
H17C1.56400.11930.28440.046*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0284 (3)0.0359 (3)0.0357 (3)−0.01063 (19)0.00829 (19)−0.0030 (2)
Cu10.0171 (3)0.0210 (3)0.0222 (3)−0.00342 (18)−0.00075 (18)−0.00929 (19)
S10.0190 (5)0.0249 (5)0.0240 (5)−0.0098 (4)0.0014 (3)−0.0118 (4)
S20.0192 (5)0.0238 (5)0.0253 (5)−0.0066 (4)−0.0020 (4)−0.0070 (4)
O10.0205 (14)0.0309 (15)0.0248 (14)0.0000 (12)−0.0005 (11)−0.0063 (12)
O20.0179 (14)0.0312 (16)0.0391 (17)−0.0064 (12)0.0007 (12)−0.0200 (13)
O30.0320 (17)0.0352 (16)0.0255 (15)−0.0200 (14)0.0015 (13)−0.0095 (13)
O40.0220 (14)0.0278 (14)0.0245 (14)0.0011 (11)−0.0040 (11)−0.0130 (12)
N10.0206 (16)0.0187 (15)0.0205 (15)−0.0074 (12)−0.0020 (12)−0.0063 (12)
N20.0201 (16)0.0205 (15)0.0214 (15)−0.0094 (12)−0.0014 (12)−0.0074 (12)
C10.0202 (18)0.0271 (19)0.0204 (18)−0.0047 (15)−0.0025 (14)−0.0113 (15)
C20.030 (2)0.0246 (19)0.0213 (19)0.0012 (16)−0.0058 (16)−0.0085 (15)
C30.036 (2)0.0252 (19)0.0199 (18)−0.0089 (17)−0.0040 (17)−0.0047 (15)
C40.024 (2)0.029 (2)0.0213 (18)−0.0088 (16)0.0002 (15)−0.0081 (16)
C50.0196 (18)0.0247 (19)0.028 (2)−0.0055 (15)−0.0014 (15)−0.0090 (16)
C60.0190 (18)0.0193 (17)0.0245 (18)−0.0061 (14)−0.0008 (15)−0.0081 (14)
C70.0190 (18)0.0202 (18)0.0255 (19)−0.0070 (14)0.0012 (15)−0.0084 (15)
C80.030 (2)0.021 (2)0.046 (3)−0.0012 (18)0.011 (2)−0.0033 (19)
C100.0177 (18)0.0252 (19)0.0275 (19)−0.0056 (15)−0.0009 (15)−0.0149 (16)
C110.025 (2)0.026 (2)0.029 (2)−0.0045 (16)−0.0016 (16)−0.0115 (16)
C120.029 (2)0.038 (2)0.027 (2)−0.0038 (19)−0.0042 (17)−0.0122 (18)
C130.030 (2)0.044 (3)0.032 (2)−0.0112 (19)−0.0001 (18)−0.023 (2)
C140.030 (2)0.030 (2)0.037 (2)−0.0118 (18)0.0038 (18)−0.0194 (19)
C150.024 (2)0.0241 (19)0.027 (2)−0.0099 (16)0.0023 (16)−0.0099 (16)
C160.023 (2)0.027 (2)0.038 (2)−0.0021 (16)−0.0020 (17)−0.0153 (18)
C170.031 (2)0.038 (2)0.031 (2)−0.0086 (19)−0.0062 (18)−0.0181 (19)

Geometric parameters (Å, °)

Br1—C41.902 (4)C5—H50.9500
Cu1—O11.894 (3)C6—C71.472 (5)
Cu1—O41.986 (3)C7—C81.501 (6)
Cu1—N11.967 (3)C8—H8A0.9800
Cu1—N2i2.026 (3)C8—H8B0.9800
S1—O31.445 (3)C8—H8C0.9800
S1—O21.450 (3)C10—C111.388 (6)
S1—N21.626 (3)C10—C151.390 (6)
S1—C101.772 (4)C11—C121.391 (6)
S2—O41.537 (3)C11—H110.9500
S2—C171.779 (4)C12—C131.387 (7)
S2—C161.781 (4)C12—H120.9500
O1—C11.310 (5)C13—C141.389 (7)
N1—C71.295 (5)C13—H130.9500
N1—N21.423 (4)C14—C151.388 (6)
N2—Cu1i2.026 (3)C14—H140.9500
C1—C21.410 (6)C15—H150.9500
C1—C61.438 (5)C16—H16A0.9800
C2—C31.372 (6)C16—H16B0.9800
C2—H20.9500C16—H16C0.9800
C3—C41.388 (6)C17—H17A0.9800
C3—H30.9500C17—H17B0.9800
C4—C51.374 (6)C17—H17C0.9800
C5—C61.407 (6)
O1—Cu1—N189.77 (13)C1—C6—C7122.5 (4)
O1—Cu1—O491.02 (13)N1—C7—C6119.4 (3)
N1—Cu1—O4167.44 (13)N1—C7—C8120.8 (4)
O1—Cu1—N2i153.28 (14)C6—C7—C8119.7 (4)
N1—Cu1—N2i93.89 (13)C7—C8—H8A109.5
O4—Cu1—N2i91.03 (13)C7—C8—H8B109.5
O3—S1—O2118.67 (19)H8A—C8—H8B109.5
O3—S1—N2105.18 (18)C7—C8—H8C109.5
O2—S1—N2112.07 (17)H8A—C8—H8C109.5
O3—S1—C10107.86 (19)H8B—C8—H8C109.5
O2—S1—C10106.05 (19)C11—C10—C15121.3 (4)
N2—S1—C10106.37 (18)C11—C10—S1119.2 (3)
O4—S2—C17105.9 (2)C15—C10—S1119.5 (3)
O4—S2—C16102.9 (2)C10—C11—C12118.8 (4)
C17—S2—C1698.1 (2)C10—C11—H11120.6
C1—O1—Cu1121.3 (3)C12—C11—H11120.6
S2—O4—Cu1120.97 (17)C13—C12—C11120.3 (4)
C7—N1—N2117.5 (3)C13—C12—H12119.8
C7—N1—Cu1127.0 (3)C11—C12—H12119.8
N2—N1—Cu1114.7 (2)C12—C13—C14120.3 (4)
N1—N2—S1108.2 (2)C12—C13—H13119.9
N1—N2—Cu1i122.8 (2)C14—C13—H13119.9
S1—N2—Cu1i105.85 (17)C15—C14—C13119.9 (4)
O1—C1—C2117.5 (4)C15—C14—H14120.0
O1—C1—C6125.2 (4)C13—C14—H14120.0
C2—C1—C6117.3 (4)C14—C15—C10119.3 (4)
C3—C2—C1122.9 (4)C14—C15—H15120.4
C3—C2—H2118.5C10—C15—H15120.4
C1—C2—H2118.5S2—C16—H16A109.5
C2—C3—C4119.0 (4)S2—C16—H16B109.5
C2—C3—H3120.5H16A—C16—H16B109.5
C4—C3—H3120.5S2—C16—H16C109.5
C5—C4—C3120.7 (4)H16A—C16—H16C109.5
C5—C4—Br1119.9 (3)H16B—C16—H16C109.5
C3—C4—Br1119.3 (3)S2—C17—H17A109.5
C4—C5—C6121.5 (4)S2—C17—H17B109.5
C4—C5—H5119.2H17A—C17—H17B109.5
C6—C5—H5119.2S2—C17—H17C109.5
C5—C6—C1118.4 (4)H17A—C17—H17C109.5
C5—C6—C7119.0 (4)H17B—C17—H17C109.5
N1—Cu1—O1—C140.0 (3)C3—C4—C5—C6−1.3 (7)
O4—Cu1—O1—C1−152.5 (3)Br1—C4—C5—C6−178.1 (3)
N2i—Cu1—O1—C1−58.2 (5)C4—C5—C6—C1−1.1 (6)
C17—S2—O4—Cu1−58.7 (3)C4—C5—C6—C7−177.5 (4)
C16—S2—O4—Cu1−161.2 (2)O1—C1—C6—C5−177.2 (4)
O1—Cu1—O4—S2−23.1 (2)C2—C1—C6—C53.2 (6)
N1—Cu1—O4—S270.5 (7)O1—C1—C6—C7−0.9 (6)
N2i—Cu1—O4—S2−176.4 (2)C2—C1—C6—C7179.6 (4)
O1—Cu1—N1—C7−34.4 (4)N2—N1—C7—C6−174.7 (3)
O4—Cu1—N1—C7−128.1 (6)Cu1—N1—C7—C615.4 (5)
N2i—Cu1—N1—C7119.1 (3)N2—N1—C7—C85.6 (6)
O1—Cu1—N1—N2155.5 (3)Cu1—N1—C7—C8−164.3 (4)
O4—Cu1—N1—N261.8 (7)C5—C6—C7—N1−174.6 (4)
N2i—Cu1—N1—N2−51.0 (3)C1—C6—C7—N19.1 (6)
C7—N1—N2—S1132.6 (3)C5—C6—C7—C85.1 (6)
Cu1—N1—N2—S1−56.4 (3)C1—C6—C7—C8−171.2 (4)
C7—N1—N2—Cu1i−103.8 (4)O3—S1—C10—C11−163.2 (3)
Cu1—N1—N2—Cu1i67.3 (3)O2—S1—C10—C11−35.1 (4)
O3—S1—N2—N1166.0 (2)N2—S1—C10—C1184.4 (4)
O2—S1—N2—N135.8 (3)O3—S1—C10—C1516.4 (4)
C10—S1—N2—N1−79.7 (3)O2—S1—C10—C15144.5 (3)
O3—S1—N2—Cu1i32.7 (2)N2—S1—C10—C15−96.0 (3)
O2—S1—N2—Cu1i−97.6 (2)C15—C10—C11—C12−0.7 (6)
C10—S1—N2—Cu1i146.95 (18)S1—C10—C11—C12178.8 (3)
Cu1—O1—C1—C2148.7 (3)C10—C11—C12—C13−0.9 (7)
Cu1—O1—C1—C6−30.8 (5)C11—C12—C13—C142.1 (7)
O1—C1—C2—C3177.1 (4)C12—C13—C14—C15−1.7 (7)
C6—C1—C2—C3−3.3 (6)C13—C14—C15—C100.1 (7)
C1—C2—C3—C41.1 (7)C11—C10—C15—C141.1 (6)
C2—C3—C4—C51.3 (7)S1—C10—C15—C14−178.5 (3)
C2—C3—C4—Br1178.2 (3)

Symmetry codes: (i) −x+2, −y+1, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2588).

References

  • Ali, H. M., Laila, M., Wan Jefrey, B. & Ng, S. W. (2007). Acta Cryst. E63, o1617–o1618.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2005). APEX2 (Version 2.0-2) and SAINT (Version 7.12A). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2008). publCIF In preparation.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography