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 ▶).
Experimental
Crystal data
[Cu2(C15H11BrN2O3S)2(C2H6OS)2]
M r = 1017.77
Triclinic,
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
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002201/lh2588Isup2.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)
.
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 = 1017.77 | F(000) = 510 |
| Triclinic, P1 | Dx = 1.778 Mg m−3 |
| 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 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
| 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 Å−3 |
| 0 restraints | Δρmin = −0.89 e Å−3 |
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
- 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. [DOI] [PubMed]
- 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
Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002201/lh2588Isup2.hkl
Additional supplementary materials: crystallographic information; 3D view; checkCIF report

