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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Jan 25;64(Pt 2):m414. doi: 10.1107/S1600536808002201

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)]

Hapipah M Ali a, Musalem Laila a, Razali M Rizal a, Seik Weng Ng a,*
PMCID: PMC2960193  PMID: 21201360

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).graphic file with name e-64-0m414-scheme1.jpg

Experimental

Crystal data

  • [Cu2(C15H11BrN2O3S)2(C2H6OS)2]

  • M r = 1017.77

  • Triclinic, Inline graphic

  • 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) 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); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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).

Supplementary Material

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

e-64-0m414-sup1.cif (19.3KB, cif)

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

e-64-0m414-Isup2.hkl (211.5KB, hkl)

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

Table 1. Selected bond lengths (Å).

Cu1—O1 1.894 (3)
Cu1—O4 1.986 (3)
Cu1—N1 1.967 (3)
Cu1—N2i 2.026 (3)

Symmetry code: (i) Inline graphic.

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.

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 = 1017.77 F(000) = 510
Triclinic, P1 Dx = 1.778 Mg m3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 8.0831 (1) Å Cell parameters from 7546 reflections
b = 10.4972 (2) Å θ = 2.7–31.0°
c = 12.9481 (2) Å µ = 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 diffractometer 4318 independent reflections
Radiation source: medium-focus sealed tube 3788 reflections with I > 2σ(I)
Graphite Rint = 0.027
φ and ω scans θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −10→10
Tmin = 0.335, Tmax = 0.542 k = −13→13
12330 measured reflections l = −16→16

Refinement

Refinement on F2 Primary atom site location: structure-invariant direct methods
Least-squares matrix: full Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151 H-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 parameters Δρmax = 1.75 e Å3
0 restraints Δρmin = −0.89 e Å3

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

x y z Uiso*/Ueq
Br1 0.33316 (6) 0.23924 (5) 0.54963 (4) 0.03789 (17)
Cu1 1.09563 (6) 0.32031 (5) 0.10740 (4) 0.02020 (15)
S1 1.13219 (13) 0.63204 (10) 0.05283 (8) 0.0213 (2)
S2 1.41379 (13) 0.06832 (10) 0.18255 (8) 0.0230 (2)
O1 1.0528 (4) 0.2167 (3) 0.2622 (3) 0.0285 (6)
O2 1.2628 (4) 0.4956 (3) 0.0677 (3) 0.0278 (6)
O3 1.1615 (4) 0.7489 (3) −0.0472 (3) 0.0292 (7)
O4 1.3150 (4) 0.1704 (3) 0.0840 (2) 0.0253 (6)
N1 0.9142 (4) 0.4879 (3) 0.1354 (3) 0.0195 (6)
N2 0.9352 (4) 0.6205 (3) 0.0558 (3) 0.0198 (6)
C1 0.8917 (5) 0.2298 (4) 0.3191 (3) 0.0219 (8)
C2 0.8558 (6) 0.1098 (5) 0.4082 (3) 0.0269 (9)
H2 0.9472 0.0236 0.4212 0.032*
C3 0.6946 (6) 0.1120 (5) 0.4770 (3) 0.0274 (9)
H3 0.6759 0.0294 0.5370 0.033*
C4 0.5591 (6) 0.2368 (5) 0.4575 (3) 0.0249 (8)
C5 0.5843 (5) 0.3557 (4) 0.3695 (4) 0.0243 (8)
H5 0.4889 0.4393 0.3569 0.029*
C6 0.7481 (5) 0.3565 (4) 0.2975 (3) 0.0208 (7)
C7 0.7691 (5) 0.4889 (4) 0.2075 (3) 0.0217 (8)
C8 0.6221 (7) 0.6230 (5) 0.1999 (5) 0.0392 (12)
H8A 0.6631 0.7033 0.1428 0.059*
H8B 0.5875 0.6396 0.2731 0.059*
H8C 0.5198 0.6135 0.1788 0.059*
C10 1.1190 (5) 0.6831 (4) 0.1713 (3) 0.0220 (8)
C11 1.1381 (6) 0.5793 (5) 0.2752 (4) 0.0269 (8)
H11 1.1558 0.4822 0.2833 0.032*
C12 1.1307 (6) 0.6200 (5) 0.3673 (4) 0.0318 (9)
H12 1.1418 0.5505 0.4393 0.038*
C13 1.1072 (6) 0.7618 (5) 0.3547 (4) 0.0327 (10)
H13 1.1064 0.7884 0.4174 0.039*
C14 1.0849 (6) 0.8649 (5) 0.2507 (4) 0.0304 (9)
H14 1.0656 0.9622 0.2429 0.036*
C15 1.0910 (6) 0.8258 (4) 0.1583 (4) 0.0249 (8)
H15 1.0761 0.8957 0.0869 0.030*
C16 1.6285 (6) 0.0005 (5) 0.1132 (4) 0.0294 (9)
H16A 1.6190 −0.0542 0.0690 0.044*
H16B 1.7060 −0.0613 0.1694 0.044*
H16C 1.6786 0.0797 0.0631 0.044*
C17 1.4719 (6) 0.1775 (5) 0.2371 (4) 0.0310 (9)
H17A 1.3669 0.2215 0.2823 0.046*
H17B 1.5168 0.2519 0.1746 0.046*
H17C 1.5640 0.1193 0.2844 0.046*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
Br1 0.0284 (3) 0.0359 (3) 0.0357 (3) −0.01063 (19) 0.00829 (19) −0.0030 (2)
Cu1 0.0171 (3) 0.0210 (3) 0.0222 (3) −0.00342 (18) −0.00075 (18) −0.00929 (19)
S1 0.0190 (5) 0.0249 (5) 0.0240 (5) −0.0098 (4) 0.0014 (3) −0.0118 (4)
S2 0.0192 (5) 0.0238 (5) 0.0253 (5) −0.0066 (4) −0.0020 (4) −0.0070 (4)
O1 0.0205 (14) 0.0309 (15) 0.0248 (14) 0.0000 (12) −0.0005 (11) −0.0063 (12)
O2 0.0179 (14) 0.0312 (16) 0.0391 (17) −0.0064 (12) 0.0007 (12) −0.0200 (13)
O3 0.0320 (17) 0.0352 (16) 0.0255 (15) −0.0200 (14) 0.0015 (13) −0.0095 (13)
O4 0.0220 (14) 0.0278 (14) 0.0245 (14) 0.0011 (11) −0.0040 (11) −0.0130 (12)
N1 0.0206 (16) 0.0187 (15) 0.0205 (15) −0.0074 (12) −0.0020 (12) −0.0063 (12)
N2 0.0201 (16) 0.0205 (15) 0.0214 (15) −0.0094 (12) −0.0014 (12) −0.0074 (12)
C1 0.0202 (18) 0.0271 (19) 0.0204 (18) −0.0047 (15) −0.0025 (14) −0.0113 (15)
C2 0.030 (2) 0.0246 (19) 0.0213 (19) 0.0012 (16) −0.0058 (16) −0.0085 (15)
C3 0.036 (2) 0.0252 (19) 0.0199 (18) −0.0089 (17) −0.0040 (17) −0.0047 (15)
C4 0.024 (2) 0.029 (2) 0.0213 (18) −0.0088 (16) 0.0002 (15) −0.0081 (16)
C5 0.0196 (18) 0.0247 (19) 0.028 (2) −0.0055 (15) −0.0014 (15) −0.0090 (16)
C6 0.0190 (18) 0.0193 (17) 0.0245 (18) −0.0061 (14) −0.0008 (15) −0.0081 (14)
C7 0.0190 (18) 0.0202 (18) 0.0255 (19) −0.0070 (14) 0.0012 (15) −0.0084 (15)
C8 0.030 (2) 0.021 (2) 0.046 (3) −0.0012 (18) 0.011 (2) −0.0033 (19)
C10 0.0177 (18) 0.0252 (19) 0.0275 (19) −0.0056 (15) −0.0009 (15) −0.0149 (16)
C11 0.025 (2) 0.026 (2) 0.029 (2) −0.0045 (16) −0.0016 (16) −0.0115 (16)
C12 0.029 (2) 0.038 (2) 0.027 (2) −0.0038 (19) −0.0042 (17) −0.0122 (18)
C13 0.030 (2) 0.044 (3) 0.032 (2) −0.0112 (19) −0.0001 (18) −0.023 (2)
C14 0.030 (2) 0.030 (2) 0.037 (2) −0.0118 (18) 0.0038 (18) −0.0194 (19)
C15 0.024 (2) 0.0241 (19) 0.027 (2) −0.0099 (16) 0.0023 (16) −0.0099 (16)
C16 0.023 (2) 0.027 (2) 0.038 (2) −0.0021 (16) −0.0020 (17) −0.0153 (18)
C17 0.031 (2) 0.038 (2) 0.031 (2) −0.0086 (19) −0.0062 (18) −0.0181 (19)

Geometric parameters (Å, °)

Br1—C4 1.902 (4) C5—H5 0.9500
Cu1—O1 1.894 (3) C6—C7 1.472 (5)
Cu1—O4 1.986 (3) C7—C8 1.501 (6)
Cu1—N1 1.967 (3) C8—H8A 0.9800
Cu1—N2i 2.026 (3) C8—H8B 0.9800
S1—O3 1.445 (3) C8—H8C 0.9800
S1—O2 1.450 (3) C10—C11 1.388 (6)
S1—N2 1.626 (3) C10—C15 1.390 (6)
S1—C10 1.772 (4) C11—C12 1.391 (6)
S2—O4 1.537 (3) C11—H11 0.9500
S2—C17 1.779 (4) C12—C13 1.387 (7)
S2—C16 1.781 (4) C12—H12 0.9500
O1—C1 1.310 (5) C13—C14 1.389 (7)
N1—C7 1.295 (5) C13—H13 0.9500
N1—N2 1.423 (4) C14—C15 1.388 (6)
N2—Cu1i 2.026 (3) C14—H14 0.9500
C1—C2 1.410 (6) C15—H15 0.9500
C1—C6 1.438 (5) C16—H16A 0.9800
C2—C3 1.372 (6) C16—H16B 0.9800
C2—H2 0.9500 C16—H16C 0.9800
C3—C4 1.388 (6) C17—H17A 0.9800
C3—H3 0.9500 C17—H17B 0.9800
C4—C5 1.374 (6) C17—H17C 0.9800
C5—C6 1.407 (6)
O1—Cu1—N1 89.77 (13) C1—C6—C7 122.5 (4)
O1—Cu1—O4 91.02 (13) N1—C7—C6 119.4 (3)
N1—Cu1—O4 167.44 (13) N1—C7—C8 120.8 (4)
O1—Cu1—N2i 153.28 (14) C6—C7—C8 119.7 (4)
N1—Cu1—N2i 93.89 (13) C7—C8—H8A 109.5
O4—Cu1—N2i 91.03 (13) C7—C8—H8B 109.5
O3—S1—O2 118.67 (19) H8A—C8—H8B 109.5
O3—S1—N2 105.18 (18) C7—C8—H8C 109.5
O2—S1—N2 112.07 (17) H8A—C8—H8C 109.5
O3—S1—C10 107.86 (19) H8B—C8—H8C 109.5
O2—S1—C10 106.05 (19) C11—C10—C15 121.3 (4)
N2—S1—C10 106.37 (18) C11—C10—S1 119.2 (3)
O4—S2—C17 105.9 (2) C15—C10—S1 119.5 (3)
O4—S2—C16 102.9 (2) C10—C11—C12 118.8 (4)
C17—S2—C16 98.1 (2) C10—C11—H11 120.6
C1—O1—Cu1 121.3 (3) C12—C11—H11 120.6
S2—O4—Cu1 120.97 (17) C13—C12—C11 120.3 (4)
C7—N1—N2 117.5 (3) C13—C12—H12 119.8
C7—N1—Cu1 127.0 (3) C11—C12—H12 119.8
N2—N1—Cu1 114.7 (2) C12—C13—C14 120.3 (4)
N1—N2—S1 108.2 (2) C12—C13—H13 119.9
N1—N2—Cu1i 122.8 (2) C14—C13—H13 119.9
S1—N2—Cu1i 105.85 (17) C15—C14—C13 119.9 (4)
O1—C1—C2 117.5 (4) C15—C14—H14 120.0
O1—C1—C6 125.2 (4) C13—C14—H14 120.0
C2—C1—C6 117.3 (4) C14—C15—C10 119.3 (4)
C3—C2—C1 122.9 (4) C14—C15—H15 120.4
C3—C2—H2 118.5 C10—C15—H15 120.4
C1—C2—H2 118.5 S2—C16—H16A 109.5
C2—C3—C4 119.0 (4) S2—C16—H16B 109.5
C2—C3—H3 120.5 H16A—C16—H16B 109.5
C4—C3—H3 120.5 S2—C16—H16C 109.5
C5—C4—C3 120.7 (4) H16A—C16—H16C 109.5
C5—C4—Br1 119.9 (3) H16B—C16—H16C 109.5
C3—C4—Br1 119.3 (3) S2—C17—H17A 109.5
C4—C5—C6 121.5 (4) S2—C17—H17B 109.5
C4—C5—H5 119.2 H17A—C17—H17B 109.5
C6—C5—H5 119.2 S2—C17—H17C 109.5
C5—C6—C1 118.4 (4) H17A—C17—H17C 109.5
C5—C6—C7 119.0 (4) H17B—C17—H17C 109.5
N1—Cu1—O1—C1 40.0 (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—C5 3.2 (6)
N1—Cu1—O4—S2 70.5 (7) O1—C1—C6—C7 −0.9 (6)
N2i—Cu1—O4—S2 −176.4 (2) C2—C1—C6—C7 179.6 (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—C6 15.4 (5)
N2i—Cu1—N1—C7 119.1 (3) N2—N1—C7—C8 5.6 (6)
O1—Cu1—N1—N2 155.5 (3) Cu1—N1—C7—C8 −164.3 (4)
O4—Cu1—N1—N2 61.8 (7) C5—C6—C7—N1 −174.6 (4)
N2i—Cu1—N1—N2 −51.0 (3) C1—C6—C7—N1 9.1 (6)
C7—N1—N2—S1 132.6 (3) C5—C6—C7—C8 5.1 (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—Cu1i 67.3 (3) O2—S1—C10—C11 −35.1 (4)
O3—S1—N2—N1 166.0 (2) N2—S1—C10—C11 84.4 (4)
O2—S1—N2—N1 35.8 (3) O3—S1—C10—C15 16.4 (4)
C10—S1—N2—N1 −79.7 (3) O2—S1—C10—C15 144.5 (3)
O3—S1—N2—Cu1i 32.7 (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—Cu1i 146.95 (18) S1—C10—C11—C12 178.8 (3)
Cu1—O1—C1—C2 148.7 (3) C10—C11—C12—C13 −0.9 (7)
Cu1—O1—C1—C6 −30.8 (5) C11—C12—C13—C14 2.1 (7)
O1—C1—C2—C3 177.1 (4) C12—C13—C14—C15 −1.7 (7)
C6—C1—C2—C3 −3.3 (6) C13—C14—C15—C10 0.1 (7)
C1—C2—C3—C4 1.1 (7) C11—C10—C15—C14 1.1 (6)
C2—C3—C4—C5 1.3 (7) S1—C10—C15—C14 −178.5 (3)
C2—C3—C4—Br1 178.2 (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

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

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-64-0m414-sup1.cif (19.3KB, cif)

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

e-64-0m414-Isup2.hkl (211.5KB, hkl)

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


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