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Acta Cryst. (2008). E64, m414    [ doi:10.1107/S1600536808002201 ]

Bis{[mu]-N'-[1-(5-bromo-2-oxidophenyl)ethylidene]benzenesulfonohydrazidato}-[kappa]3O2,N':N;[kappa]3N:O2,N'-bis[(dimethyl sulfoxide-[kappa]O)copper(II)]

H. M. Ali, M. Laila, R. M. Rizal and S. W. Ng

Abstract top

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 top

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

Experimental top

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 top

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.

Computing details top

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

Figures top
[Figure 1] 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].
Bis{µ-N'-[1-(5-bromo-2- oxidophenyl)ethylidene]benzenesulfonohydrazidato}- κ3O2,N':N;κ3N:N',O2-bis[(dimethyl sulfoxide-κO)copper(II)] top
Crystal data top
[Cu2(C15H11BrN2O3S)2(C2H6OS)2]Z = 1
Mr = 1017.77F(000) = 510
Triclinic, P1Dx = 1.778 Mg m−3
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 mm−1
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 top
Bruker APEXII
diffractometer		4318 independent reflections
Radiation source: medium-focus sealed tube3788 reflections with I > 2σ(I)
GraphiteRint = 0.027
φ 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 top
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 = 1.21 w = 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 Å−3
0 restraintsΔρmin = −0.89 e Å−3
Crystal data top
[Cu2(C15H11BrN2O3S)2(C2H6OS)2]γ = 70.691 (1)°
Mr = 1017.77V = 950.56 (3) Å3
Triclinic, P1Z = 1
a = 8.0831 (1) ÅMo Kα radiation
b = 10.4972 (2) ŵ = 3.49 mm−1
c = 12.9481 (2) ÅT = 123 K
α = 68.157 (1)°0.40 × 0.31 × 0.20 mm
β = 74.928 (1)°
Data collection top
Bruker APEXII
diffractometer		3788 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.027
Tmin = 0.335, Tmax = 0.542θmax = 27.5°
12330 measured reflectionsStandard reflections: 0
4318 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.151Δρmax = 1.75 e Å−3
S = 1.21Δρmin = −0.89 e Å−3
4318 reflectionsAbsolute structure: ?
238 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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.
Table 1
Selected geometric parameters (Å) top
Cu1—O11.894 (3)Cu1—N11.967 (3)
Cu1—O41.986 (3)Cu1—N2i2.026 (3)
Symmetry codes: (i) −x+2, −y+1, −z.
Acknowledgements top

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.

references
References top

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.

Westrip, S. P. (2008). publCIF. In preparation.