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metal-organic compounds
cis-Bis[N′-(4-bromobenzoyl)-N,N-dimethylthioureato-κ2O,S]copper(II)
aDepartment of Chemistry, Faculty of Education, Mersin University, Mersin, TR 33169, Turkey, bDepartment of Chemistry, University of Paderborn, Paderborn D-33098, Germany, cDepartment of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey, and dDepartment of Chemistry, Emory University, Atlanta, GA 30322, USA
*Correspondence e-mail: hakan.arslan.acad@gmail.com
The 10H10BrN2OS)2], contains two independent complex molecules with almost identical conformations. Two S and two O atoms form the coordination environment of the Cu atom, resulting in a slightly distorted square-planar coordination. The S atoms are in a cis configuration. The is stabilized by weak intermolecular C—H⋯Br hydrogen-bonding interactions.
of the title compound, [Cu(CRelated literature
For the synthesis of the title compound, see: Binzet et al. (2009); Emen et al. (2005
). For complexes with thiourea derivatives, see: Sacht et al. (2000
); Arslan et al. (2009
); Avşar et al. (2002
, 2003
); Mansuroğlu et al. (2008
); Henderson et al. (2002
). For related compounds, see: Arslan et al. (2003
, 2006
). For puckering parameters, see: Cremer & Pople (1975
).
Experimental
Crystal data
|
Refinement
|
|
Data collection: SMART (Bruker, 2002); cell SAINT (Bruker, 2002
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: OLEX2 (Dolomanov et al., 2009
); software used to prepare material for publication: SHELXTL (Sheldrick, 2008
), OLEX2, publCIF (Westrip, 2010
) and Mercury (Macrae et al., 2006
).
Supporting information
10.1107/S1600536811015789/bt5534sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536811015789/bt5534Isup2.hkl
A solution of 4-bromobenzoyl chloride (0.005 M) in acetone (50 cm3) was added dropwise to a suspension of potassium thiocyanate (0.005 M) in anhydrous acetone (50 cm3). The reaction mixture was heated under reflux for 30 min and then cooled to room temperature. A solution of dimethylamine (0.005 M) in acetone (30 cm3) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 300 cm3) was added and the solution filtered. The solid product was washed with water and purified by recrystallization from ethanol: dichloromethane (1: 2). M.p.: 222–224 °C. C20H20Br2CuN4O2S2: C, 37.78; H, 3.17; N, 8.81. Found: C, 37.97; H, 3.20; N, 8.79%.
H atom positions were clearly derived from difference Fourier maps and refined using a riding model, fixing the bond lengths at 0.98 and 0.95 Å for CH3 and CH(aromatic), respectively. The displacement parameters of the H atoms were constrained with Uiso(H) = 1.2Ueq (C) or 1.5Ueq (methyl C).
Data collection: SMART (Bruker, 2002); cell
SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and Mercury (Macrae et al., 2006).[Cu(C10H10BrN2OS)2] | Z = 4 |
Mr = 635.88 | F(000) = 1260 |
Triclinic, P1 | Dx = 1.825 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.1780 (11) Å | Cell parameters from 3977 reflections |
b = 11.0028 (13) Å | θ = 2.3–28.7° |
c = 23.241 (3) Å | µ = 4.60 mm−1 |
α = 94.857 (2)° | T = 120 K |
β = 96.144 (3)° | Prism, red |
γ = 95.095 (2)° | 0.28 × 0.21 × 0.12 mm |
V = 2313.7 (5) Å3 |
Bruker SMART APEX diffractometer | 10926 independent reflections |
Radiation source: sealed tube | 8446 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ϕ and ω scans | θmax = 27.9°, θmin = 0.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −11→12 |
Tmin = 0.359, Tmax = 0.608 | k = −14→14 |
20433 measured reflections | l = −30→28 |
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)] = 0.042 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0696P)2] where P = (Fo2 + 2Fc2)/3 |
10926 reflections | (Δ/σ)max = 0.001 |
567 parameters | Δρmax = 0.98 e Å−3 |
0 restraints | Δρmin = −0.84 e Å−3 |
[Cu(C10H10BrN2OS)2] | γ = 95.095 (2)° |
Mr = 635.88 | V = 2313.7 (5) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.1780 (11) Å | Mo Kα radiation |
b = 11.0028 (13) Å | µ = 4.60 mm−1 |
c = 23.241 (3) Å | T = 120 K |
α = 94.857 (2)° | 0.28 × 0.21 × 0.12 mm |
β = 96.144 (3)° |
Bruker SMART APEX diffractometer | 10926 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 8446 reflections with I > 2σ(I) |
Tmin = 0.359, Tmax = 0.608 | Rint = 0.029 |
20433 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.117 | H-atom parameters constrained |
S = 1.00 | Δρmax = 0.98 e Å−3 |
10926 reflections | Δρmin = −0.84 e Å−3 |
567 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cu1 | 0.28252 (5) | 0.12213 (4) | 0.428728 (19) | 0.02274 (11) | |
Br1 | 0.37548 (5) | −0.19864 (4) | 0.753935 (17) | 0.03539 (11) | |
Br2 | 1.00293 (4) | 0.48331 (4) | 0.664265 (18) | 0.03169 (10) | |
S1 | 0.13289 (10) | −0.01269 (8) | 0.37520 (4) | 0.02310 (19) | |
S2 | 0.26287 (10) | 0.23785 (8) | 0.35908 (4) | 0.02323 (19) | |
O1 | 0.2935 (3) | 0.0289 (2) | 0.49212 (11) | 0.0255 (6) | |
O2 | 0.4210 (3) | 0.2305 (2) | 0.47515 (11) | 0.0250 (5) | |
N1 | 0.0876 (3) | −0.1172 (3) | 0.47730 (13) | 0.0210 (6) | |
N2 | −0.0790 (3) | −0.1706 (3) | 0.39781 (13) | 0.0240 (6) | |
N3 | 0.5181 (3) | 0.3709 (3) | 0.41560 (13) | 0.0214 (6) | |
N4 | 0.4318 (3) | 0.4184 (3) | 0.32595 (13) | 0.0240 (7) | |
C1 | 0.0445 (4) | −0.1031 (3) | 0.42136 (16) | 0.0214 (7) | |
C2 | −0.1409 (4) | −0.1633 (4) | 0.33765 (17) | 0.0308 (9) | |
H2A | −0.1534 | −0.0776 | 0.3314 | 0.046* | |
H2B | −0.2368 | −0.2121 | 0.3300 | 0.046* | |
H2C | −0.0741 | −0.1952 | 0.3112 | 0.046* | |
C3 | −0.1613 (4) | −0.2547 (4) | 0.43166 (18) | 0.0294 (8) | |
H3A | −0.1034 | −0.2607 | 0.4691 | 0.044* | |
H3B | −0.1799 | −0.3361 | 0.4101 | 0.044* | |
H3C | −0.2553 | −0.2234 | 0.4383 | 0.044* | |
C4 | 0.2079 (4) | −0.0569 (3) | 0.50652 (15) | 0.0200 (7) | |
C5 | 0.2476 (4) | −0.0921 (3) | 0.56630 (15) | 0.0211 (7) | |
C6 | 0.1521 (4) | −0.1724 (3) | 0.59169 (16) | 0.0241 (7) | |
H6A | 0.0620 | −0.2067 | 0.5701 | 0.029* | |
C7 | 0.1876 (4) | −0.2026 (3) | 0.64818 (17) | 0.0278 (8) | |
H7A | 0.1217 | −0.2559 | 0.6656 | 0.033* | |
C8 | 0.3206 (4) | −0.1534 (3) | 0.67833 (15) | 0.0252 (8) | |
C9 | 0.4182 (4) | −0.0729 (3) | 0.65460 (17) | 0.0259 (8) | |
H9A | 0.5086 | −0.0393 | 0.6762 | 0.031* | |
C10 | 0.3797 (4) | −0.0429 (3) | 0.59820 (16) | 0.0247 (8) | |
H10A | 0.4447 | 0.0120 | 0.5813 | 0.030* | |
C11 | 0.4137 (4) | 0.3472 (3) | 0.36911 (16) | 0.0213 (7) | |
C12 | 0.5545 (4) | 0.5137 (4) | 0.33028 (18) | 0.0339 (9) | |
H12A | 0.5697 | 0.5556 | 0.3697 | 0.051* | |
H12B | 0.5324 | 0.5730 | 0.3022 | 0.051* | |
H12C | 0.6440 | 0.4765 | 0.3219 | 0.051* | |
C13 | 0.3332 (4) | 0.4071 (4) | 0.27193 (16) | 0.0289 (8) | |
H13A | 0.2945 | 0.3211 | 0.2620 | 0.043* | |
H13B | 0.3873 | 0.4355 | 0.2407 | 0.043* | |
H13C | 0.2513 | 0.4571 | 0.2768 | 0.043* | |
C14 | 0.5131 (4) | 0.3156 (3) | 0.46358 (15) | 0.0207 (7) | |
C15 | 0.6319 (4) | 0.3585 (3) | 0.51186 (15) | 0.0198 (7) | |
C16 | 0.7371 (4) | 0.4549 (3) | 0.50670 (16) | 0.0269 (8) | |
H16A | 0.7326 | 0.4953 | 0.4721 | 0.032* | |
C17 | 0.8489 (4) | 0.4928 (4) | 0.55177 (17) | 0.0291 (8) | |
H17A | 0.9212 | 0.5581 | 0.5481 | 0.035* | |
C18 | 0.8525 (4) | 0.4340 (3) | 0.60154 (16) | 0.0234 (7) | |
C19 | 0.7489 (4) | 0.3378 (3) | 0.60788 (17) | 0.0272 (8) | |
H19A | 0.7529 | 0.2980 | 0.6427 | 0.033* | |
C20 | 0.6396 (4) | 0.3010 (3) | 0.56235 (16) | 0.0254 (8) | |
H20A | 0.5684 | 0.2348 | 0.5660 | 0.031* | |
Cu2 | 0.35911 (5) | 0.18310 (4) | 0.070914 (19) | 0.02242 (11) | |
Br3 | 0.00952 (4) | −0.42199 (4) | −0.175362 (17) | 0.03082 (10) | |
Br4 | 0.73008 (5) | 0.17128 (4) | −0.253135 (18) | 0.03850 (12) | |
S3 | 0.25683 (10) | 0.14812 (8) | 0.14730 (4) | 0.02390 (19) | |
S4 | 0.45871 (11) | 0.35186 (8) | 0.11731 (4) | 0.0259 (2) | |
O3 | 0.2718 (3) | 0.0415 (2) | 0.02839 (11) | 0.0256 (6) | |
O4 | 0.4483 (3) | 0.2068 (2) | 0.00413 (11) | 0.0256 (6) | |
N5 | 0.0961 (3) | −0.0513 (3) | 0.08088 (13) | 0.0216 (6) | |
N6 | 0.0270 (3) | 0.0084 (3) | 0.16917 (13) | 0.0252 (7) | |
N7 | 0.6098 (3) | 0.3874 (3) | 0.02166 (13) | 0.0228 (6) | |
N8 | 0.6605 (3) | 0.5243 (3) | 0.10071 (13) | 0.0235 (6) | |
C21 | 0.1191 (4) | 0.0278 (3) | 0.12893 (15) | 0.0205 (7) | |
C22 | −0.0890 (5) | −0.0925 (4) | 0.15936 (19) | 0.0373 (10) | |
H22A | −0.1277 | −0.1036 | 0.1181 | 0.056* | |
H22B | −0.1685 | −0.0742 | 0.1827 | 0.056* | |
H22C | −0.0490 | −0.1678 | 0.1706 | 0.056* | |
C23 | 0.0390 (4) | 0.0848 (4) | 0.22442 (16) | 0.0285 (8) | |
H23A | 0.1327 | 0.0755 | 0.2473 | 0.043* | |
H23B | −0.0426 | 0.0592 | 0.2461 | 0.043* | |
H23C | 0.0349 | 0.1708 | 0.2169 | 0.043* | |
C24 | 0.1727 (4) | −0.0415 (3) | 0.03654 (15) | 0.0200 (7) | |
C25 | 0.1355 (4) | −0.1392 (3) | −0.01296 (15) | 0.0196 (7) | |
C26 | 0.2139 (4) | −0.1347 (3) | −0.06115 (16) | 0.0228 (7) | |
H26A | 0.2928 | −0.0726 | −0.0612 | 0.027* | |
C27 | 0.1772 (4) | −0.2202 (3) | −0.10896 (16) | 0.0234 (7) | |
H27A | 0.2297 | −0.2169 | −0.1419 | 0.028* | |
C28 | 0.0628 (4) | −0.3107 (3) | −0.10794 (15) | 0.0222 (7) | |
C29 | −0.0135 (4) | −0.3181 (3) | −0.06067 (17) | 0.0278 (8) | |
H29A | −0.0906 | −0.3817 | −0.0605 | 0.033* | |
C30 | 0.0227 (4) | −0.2317 (3) | −0.01284 (16) | 0.0244 (8) | |
H30A | −0.0301 | −0.2361 | 0.0200 | 0.029* | |
C31 | 0.5819 (4) | 0.4225 (3) | 0.07554 (15) | 0.0205 (7) | |
C32 | 0.7652 (4) | 0.5938 (3) | 0.06970 (18) | 0.0315 (9) | |
H32A | 0.8643 | 0.5695 | 0.0797 | 0.047* | |
H32B | 0.7645 | 0.6816 | 0.0809 | 0.047* | |
H32C | 0.7371 | 0.5768 | 0.0277 | 0.047* | |
C33 | 0.6478 (5) | 0.5730 (4) | 0.15988 (17) | 0.0311 (9) | |
H33A | 0.5494 | 0.6001 | 0.1620 | 0.047* | |
H33B | 0.7223 | 0.6428 | 0.1713 | 0.047* | |
H33C | 0.6631 | 0.5091 | 0.1862 | 0.047* | |
C34 | 0.5439 (4) | 0.2865 (3) | −0.00926 (15) | 0.0211 (7) | |
C35 | 0.5885 (4) | 0.2613 (3) | −0.06848 (15) | 0.0211 (7) | |
C36 | 0.6950 (4) | 0.3395 (3) | −0.08950 (17) | 0.0281 (8) | |
H36A | 0.7396 | 0.4107 | −0.0660 | 0.034* | |
C37 | 0.7353 (4) | 0.3128 (4) | −0.14478 (17) | 0.0309 (9) | |
H37A | 0.8079 | 0.3654 | −0.1592 | 0.037* | |
C38 | 0.6697 (4) | 0.2099 (4) | −0.17848 (15) | 0.0266 (8) | |
C39 | 0.5635 (4) | 0.1312 (3) | −0.15925 (17) | 0.0276 (8) | |
H39A | 0.5190 | 0.0605 | −0.1831 | 0.033* | |
C40 | 0.5238 (4) | 0.1586 (3) | −0.10393 (16) | 0.0244 (8) | |
H40A | 0.4507 | 0.1057 | −0.0900 | 0.029* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cu1 | 0.0229 (2) | 0.0228 (2) | 0.0215 (2) | −0.00394 (17) | 0.00288 (18) | 0.00245 (17) |
Br1 | 0.0406 (2) | 0.0475 (3) | 0.0205 (2) | 0.01112 (19) | 0.00464 (17) | 0.00856 (17) |
Br2 | 0.0305 (2) | 0.0327 (2) | 0.0279 (2) | −0.00079 (16) | −0.00602 (16) | −0.00411 (16) |
S1 | 0.0268 (5) | 0.0224 (4) | 0.0186 (4) | −0.0055 (3) | 0.0029 (3) | 0.0018 (3) |
S2 | 0.0219 (4) | 0.0224 (4) | 0.0236 (5) | −0.0054 (3) | −0.0014 (3) | 0.0046 (3) |
O1 | 0.0259 (13) | 0.0274 (13) | 0.0217 (14) | −0.0076 (11) | 0.0007 (11) | 0.0068 (11) |
O2 | 0.0240 (13) | 0.0286 (13) | 0.0205 (13) | −0.0107 (11) | 0.0024 (10) | 0.0048 (11) |
N1 | 0.0221 (15) | 0.0215 (14) | 0.0199 (15) | −0.0009 (12) | 0.0054 (12) | 0.0037 (12) |
N2 | 0.0229 (15) | 0.0240 (15) | 0.0233 (16) | −0.0053 (12) | 0.0017 (12) | 0.0012 (12) |
N3 | 0.0220 (15) | 0.0208 (14) | 0.0201 (16) | −0.0034 (12) | 0.0020 (12) | 0.0009 (12) |
N4 | 0.0270 (16) | 0.0261 (16) | 0.0177 (16) | −0.0058 (13) | 0.0018 (13) | 0.0051 (12) |
C1 | 0.0214 (17) | 0.0166 (16) | 0.0260 (19) | 0.0018 (13) | 0.0051 (14) | −0.0014 (14) |
C2 | 0.026 (2) | 0.035 (2) | 0.027 (2) | −0.0080 (17) | −0.0052 (16) | 0.0016 (17) |
C3 | 0.028 (2) | 0.0276 (19) | 0.030 (2) | −0.0130 (16) | 0.0052 (16) | 0.0012 (16) |
C4 | 0.0207 (17) | 0.0198 (16) | 0.0193 (18) | 0.0015 (13) | 0.0033 (14) | 0.0000 (13) |
C5 | 0.0243 (18) | 0.0193 (16) | 0.0195 (18) | 0.0010 (14) | 0.0031 (14) | 0.0012 (13) |
C6 | 0.0234 (18) | 0.0239 (18) | 0.0242 (19) | −0.0016 (14) | 0.0030 (15) | 0.0024 (15) |
C7 | 0.030 (2) | 0.0271 (19) | 0.028 (2) | 0.0007 (16) | 0.0085 (16) | 0.0053 (16) |
C8 | 0.031 (2) | 0.0302 (19) | 0.0159 (18) | 0.0079 (16) | 0.0032 (15) | 0.0030 (15) |
C9 | 0.0213 (18) | 0.0299 (19) | 0.027 (2) | 0.0029 (15) | 0.0028 (15) | 0.0030 (16) |
C10 | 0.0208 (18) | 0.0254 (18) | 0.028 (2) | −0.0015 (14) | 0.0062 (15) | 0.0027 (15) |
C11 | 0.0196 (17) | 0.0184 (16) | 0.0259 (19) | 0.0016 (13) | 0.0040 (14) | 0.0011 (14) |
C12 | 0.034 (2) | 0.037 (2) | 0.028 (2) | −0.0113 (18) | 0.0008 (17) | 0.0107 (18) |
C13 | 0.031 (2) | 0.033 (2) | 0.022 (2) | −0.0026 (16) | −0.0005 (16) | 0.0062 (16) |
C14 | 0.0206 (17) | 0.0194 (16) | 0.0217 (18) | 0.0014 (13) | 0.0045 (14) | −0.0024 (14) |
C15 | 0.0216 (17) | 0.0199 (16) | 0.0181 (17) | 0.0014 (13) | 0.0046 (14) | 0.0000 (13) |
C16 | 0.034 (2) | 0.0258 (19) | 0.0196 (19) | −0.0066 (16) | −0.0014 (15) | 0.0066 (15) |
C17 | 0.033 (2) | 0.0273 (19) | 0.024 (2) | −0.0115 (16) | 0.0042 (16) | 0.0006 (15) |
C18 | 0.0233 (18) | 0.0228 (17) | 0.0214 (19) | 0.0000 (14) | −0.0018 (14) | −0.0051 (14) |
C19 | 0.033 (2) | 0.0256 (19) | 0.0214 (19) | −0.0040 (16) | 0.0014 (16) | 0.0049 (15) |
C20 | 0.029 (2) | 0.0203 (17) | 0.026 (2) | −0.0085 (14) | 0.0051 (15) | 0.0047 (15) |
Cu2 | 0.0251 (2) | 0.0211 (2) | 0.0201 (2) | −0.00261 (17) | 0.00350 (18) | 0.00064 (17) |
Br3 | 0.0370 (2) | 0.0287 (2) | 0.0227 (2) | −0.00348 (16) | −0.00316 (16) | −0.00510 (15) |
Br4 | 0.0525 (3) | 0.0426 (2) | 0.0223 (2) | 0.0032 (2) | 0.01448 (19) | 0.00322 (17) |
S3 | 0.0280 (5) | 0.0236 (4) | 0.0182 (4) | −0.0060 (4) | 0.0041 (4) | −0.0015 (3) |
S4 | 0.0328 (5) | 0.0213 (4) | 0.0224 (5) | −0.0072 (4) | 0.0093 (4) | −0.0027 (4) |
O3 | 0.0311 (14) | 0.0226 (13) | 0.0208 (14) | −0.0098 (11) | 0.0064 (11) | −0.0025 (10) |
O4 | 0.0329 (14) | 0.0243 (13) | 0.0183 (13) | −0.0085 (11) | 0.0073 (11) | 0.0006 (10) |
N5 | 0.0221 (15) | 0.0241 (15) | 0.0170 (15) | −0.0012 (12) | −0.0009 (12) | 0.0007 (12) |
N6 | 0.0260 (16) | 0.0285 (16) | 0.0195 (16) | −0.0073 (13) | 0.0062 (13) | −0.0013 (13) |
N7 | 0.0256 (16) | 0.0223 (15) | 0.0210 (16) | −0.0020 (12) | 0.0067 (12) | 0.0040 (12) |
N8 | 0.0295 (16) | 0.0210 (15) | 0.0188 (16) | −0.0060 (12) | 0.0054 (13) | −0.0003 (12) |
C21 | 0.0209 (17) | 0.0198 (16) | 0.0207 (18) | −0.0002 (13) | 0.0011 (14) | 0.0051 (14) |
C22 | 0.033 (2) | 0.042 (2) | 0.034 (2) | −0.0151 (19) | 0.0097 (18) | −0.0004 (19) |
C23 | 0.032 (2) | 0.0298 (19) | 0.024 (2) | −0.0039 (16) | 0.0099 (16) | −0.0006 (16) |
C24 | 0.0202 (17) | 0.0179 (16) | 0.0204 (18) | −0.0020 (13) | −0.0005 (14) | 0.0018 (13) |
C25 | 0.0227 (18) | 0.0207 (16) | 0.0143 (17) | −0.0001 (13) | −0.0005 (13) | 0.0007 (13) |
C26 | 0.0221 (18) | 0.0221 (17) | 0.0233 (19) | −0.0040 (14) | 0.0026 (14) | 0.0033 (14) |
C27 | 0.0265 (19) | 0.0267 (18) | 0.0175 (18) | −0.0018 (15) | 0.0069 (14) | 0.0042 (14) |
C28 | 0.0280 (19) | 0.0214 (17) | 0.0146 (17) | 0.0016 (14) | −0.0051 (14) | −0.0029 (13) |
C29 | 0.027 (2) | 0.0268 (19) | 0.027 (2) | −0.0080 (15) | 0.0014 (16) | 0.0015 (16) |
C30 | 0.0275 (19) | 0.0243 (18) | 0.0206 (19) | −0.0044 (15) | 0.0048 (15) | 0.0019 (14) |
C31 | 0.0213 (17) | 0.0211 (17) | 0.0188 (18) | 0.0004 (13) | 0.0007 (14) | 0.0038 (14) |
C32 | 0.037 (2) | 0.0241 (19) | 0.032 (2) | −0.0093 (17) | 0.0070 (18) | 0.0040 (16) |
C33 | 0.040 (2) | 0.0255 (19) | 0.024 (2) | −0.0085 (17) | 0.0031 (17) | −0.0088 (16) |
C34 | 0.0250 (18) | 0.0190 (16) | 0.0199 (18) | 0.0008 (14) | 0.0046 (14) | 0.0052 (14) |
C35 | 0.0252 (18) | 0.0188 (16) | 0.0193 (18) | 0.0000 (14) | 0.0039 (14) | 0.0030 (13) |
C36 | 0.032 (2) | 0.0240 (18) | 0.027 (2) | −0.0070 (16) | 0.0071 (16) | 0.0016 (15) |
C37 | 0.034 (2) | 0.029 (2) | 0.030 (2) | −0.0044 (17) | 0.0117 (17) | 0.0039 (16) |
C38 | 0.035 (2) | 0.032 (2) | 0.0140 (18) | 0.0074 (17) | 0.0064 (15) | 0.0038 (15) |
C39 | 0.035 (2) | 0.0251 (18) | 0.022 (2) | −0.0010 (16) | 0.0028 (16) | 0.0014 (15) |
C40 | 0.0286 (19) | 0.0218 (17) | 0.0222 (19) | −0.0025 (15) | 0.0047 (15) | 0.0014 (14) |
Cu1—O2 | 1.850 (3) | Cu2—O3 | 1.842 (2) |
Cu1—O1 | 1.864 (3) | Cu2—O4 | 1.857 (2) |
Cu1—S1 | 2.1433 (10) | Cu2—S3 | 2.1423 (10) |
Cu1—S2 | 2.1451 (10) | Cu2—S4 | 2.1435 (10) |
Br1—C8 | 1.895 (4) | Br3—C28 | 1.897 (3) |
Br2—C18 | 1.904 (4) | Br4—C38 | 1.903 (4) |
S1—C1 | 1.738 (4) | S3—C21 | 1.739 (4) |
S2—C11 | 1.734 (4) | S4—C31 | 1.741 (4) |
O1—C4 | 1.265 (4) | O3—C24 | 1.271 (4) |
O2—C14 | 1.270 (4) | O4—C34 | 1.266 (4) |
N1—C4 | 1.324 (4) | N5—C24 | 1.315 (4) |
N1—C1 | 1.344 (5) | N5—C21 | 1.342 (4) |
N2—C1 | 1.336 (4) | N6—C21 | 1.344 (4) |
N2—C2 | 1.464 (5) | N6—C22 | 1.454 (5) |
N2—C3 | 1.474 (5) | N6—C23 | 1.462 (5) |
N3—C14 | 1.318 (5) | N7—C34 | 1.329 (5) |
N3—C11 | 1.356 (4) | N7—C31 | 1.337 (4) |
N4—C11 | 1.339 (4) | N8—C31 | 1.332 (4) |
N4—C13 | 1.456 (5) | N8—C33 | 1.453 (5) |
N4—C12 | 1.459 (5) | N8—C32 | 1.463 (5) |
C2—H2A | 0.9800 | C22—H22A | 0.9800 |
C2—H2B | 0.9800 | C22—H22B | 0.9800 |
C2—H2C | 0.9800 | C22—H22C | 0.9800 |
C3—H3A | 0.9800 | C23—H23A | 0.9800 |
C3—H3B | 0.9800 | C23—H23B | 0.9800 |
C3—H3C | 0.9800 | C23—H23C | 0.9800 |
C4—C5 | 1.490 (5) | C24—C25 | 1.496 (5) |
C5—C10 | 1.391 (5) | C25—C30 | 1.386 (5) |
C5—C6 | 1.400 (5) | C25—C26 | 1.397 (5) |
C6—C7 | 1.393 (5) | C26—C27 | 1.386 (5) |
C6—H6A | 0.9500 | C26—H26A | 0.9500 |
C7—C8 | 1.382 (5) | C27—C28 | 1.385 (5) |
C7—H7A | 0.9500 | C27—H27A | 0.9500 |
C8—C9 | 1.393 (5) | C28—C29 | 1.369 (5) |
C9—C10 | 1.395 (5) | C29—C30 | 1.391 (5) |
C9—H9A | 0.9500 | C29—H29A | 0.9500 |
C10—H10A | 0.9500 | C30—H30A | 0.9500 |
C12—H12A | 0.9800 | C32—H32A | 0.9800 |
C12—H12B | 0.9800 | C32—H32B | 0.9800 |
C12—H12C | 0.9800 | C32—H32C | 0.9800 |
C13—H13A | 0.9800 | C33—H33A | 0.9800 |
C13—H13B | 0.9800 | C33—H33B | 0.9800 |
C13—H13C | 0.9800 | C33—H33C | 0.9800 |
C14—C15 | 1.493 (5) | C34—C35 | 1.488 (5) |
C15—C20 | 1.377 (5) | C35—C40 | 1.389 (5) |
C15—C16 | 1.391 (5) | C35—C36 | 1.399 (5) |
C16—C17 | 1.394 (5) | C36—C37 | 1.390 (5) |
C16—H16A | 0.9500 | C36—H36A | 0.9500 |
C17—C18 | 1.371 (5) | C37—C38 | 1.373 (5) |
C17—H17A | 0.9500 | C37—H37A | 0.9500 |
C18—C19 | 1.387 (5) | C38—C39 | 1.381 (5) |
C19—C20 | 1.385 (5) | C39—C40 | 1.390 (5) |
C19—H19A | 0.9500 | C39—H39A | 0.9500 |
C20—H20A | 0.9500 | C40—H40A | 0.9500 |
O2—Cu1—O1 | 84.47 (11) | O3—Cu2—O4 | 83.73 (11) |
O2—Cu1—S1 | 176.03 (9) | O3—Cu2—S3 | 94.44 (8) |
O1—Cu1—S1 | 93.66 (8) | O4—Cu2—S3 | 177.74 (8) |
O2—Cu1—S2 | 94.24 (8) | O3—Cu2—S4 | 177.64 (9) |
O1—Cu1—S2 | 176.26 (9) | O4—Cu2—S4 | 94.60 (8) |
S1—Cu1—S2 | 87.84 (4) | S3—Cu2—S4 | 87.27 (4) |
C1—S1—Cu1 | 107.27 (13) | C21—S3—Cu2 | 108.25 (12) |
C11—S2—Cu1 | 108.03 (13) | C31—S4—Cu2 | 109.18 (12) |
C4—O1—Cu1 | 132.3 (2) | C24—O3—Cu2 | 134.5 (2) |
C14—O2—Cu1 | 132.4 (2) | C34—O4—Cu2 | 134.3 (2) |
C4—N1—C1 | 122.7 (3) | C24—N5—C21 | 123.0 (3) |
C1—N2—C2 | 121.9 (3) | C21—N6—C22 | 120.4 (3) |
C1—N2—C3 | 121.5 (3) | C21—N6—C23 | 122.5 (3) |
C2—N2—C3 | 116.6 (3) | C22—N6—C23 | 117.1 (3) |
C14—N3—C11 | 123.1 (3) | C34—N7—C31 | 123.3 (3) |
C11—N4—C13 | 123.4 (3) | C31—N8—C33 | 122.6 (3) |
C11—N4—C12 | 121.3 (3) | C31—N8—C32 | 121.2 (3) |
C13—N4—C12 | 115.3 (3) | C33—N8—C32 | 116.2 (3) |
N2—C1—N1 | 115.7 (3) | N5—C21—N6 | 115.7 (3) |
N2—C1—S1 | 116.1 (3) | N5—C21—S3 | 128.6 (3) |
N1—C1—S1 | 128.2 (3) | N6—C21—S3 | 115.7 (3) |
N2—C2—H2A | 109.5 | N6—C22—H22A | 109.5 |
N2—C2—H2B | 109.5 | N6—C22—H22B | 109.5 |
H2A—C2—H2B | 109.5 | H22A—C22—H22B | 109.5 |
N2—C2—H2C | 109.5 | N6—C22—H22C | 109.5 |
H2A—C2—H2C | 109.5 | H22A—C22—H22C | 109.5 |
H2B—C2—H2C | 109.5 | H22B—C22—H22C | 109.5 |
N2—C3—H3A | 109.5 | N6—C23—H23A | 109.5 |
N2—C3—H3B | 109.5 | N6—C23—H23B | 109.5 |
H3A—C3—H3B | 109.5 | H23A—C23—H23B | 109.5 |
N2—C3—H3C | 109.5 | N6—C23—H23C | 109.5 |
H3A—C3—H3C | 109.5 | H23A—C23—H23C | 109.5 |
H3B—C3—H3C | 109.5 | H23B—C23—H23C | 109.5 |
O1—C4—N1 | 129.9 (3) | O3—C24—N5 | 129.5 (3) |
O1—C4—C5 | 114.2 (3) | O3—C24—C25 | 114.3 (3) |
N1—C4—C5 | 115.8 (3) | N5—C24—C25 | 116.1 (3) |
C10—C5—C6 | 119.0 (3) | C30—C25—C26 | 119.4 (3) |
C10—C5—C4 | 120.1 (3) | C30—C25—C24 | 121.7 (3) |
C6—C5—C4 | 120.9 (3) | C26—C25—C24 | 118.9 (3) |
C7—C6—C5 | 120.9 (4) | C27—C26—C25 | 120.3 (3) |
C7—C6—H6A | 119.6 | C27—C26—H26A | 119.8 |
C5—C6—H6A | 119.6 | C25—C26—H26A | 119.8 |
C8—C7—C6 | 118.6 (4) | C28—C27—C26 | 119.0 (3) |
C8—C7—H7A | 120.7 | C28—C27—H27A | 120.5 |
C6—C7—H7A | 120.7 | C26—C27—H27A | 120.5 |
C7—C8—C9 | 122.2 (3) | C29—C28—C27 | 121.5 (3) |
C7—C8—Br1 | 119.5 (3) | C29—C28—Br3 | 120.4 (3) |
C9—C8—Br1 | 118.3 (3) | C27—C28—Br3 | 118.0 (3) |
C8—C9—C10 | 118.2 (4) | C28—C29—C30 | 119.4 (3) |
C8—C9—H9A | 120.9 | C28—C29—H29A | 120.3 |
C10—C9—H9A | 120.9 | C30—C29—H29A | 120.3 |
C5—C10—C9 | 121.1 (3) | C25—C30—C29 | 120.3 (3) |
C5—C10—H10A | 119.4 | C25—C30—H30A | 119.9 |
C9—C10—H10A | 119.4 | C29—C30—H30A | 119.9 |
N4—C11—N3 | 114.6 (3) | N8—C31—N7 | 115.4 (3) |
N4—C11—S2 | 117.0 (3) | N8—C31—S4 | 115.9 (3) |
N3—C11—S2 | 128.4 (3) | N7—C31—S4 | 128.7 (3) |
N4—C12—H12A | 109.5 | N8—C32—H32A | 109.5 |
N4—C12—H12B | 109.5 | N8—C32—H32B | 109.5 |
H12A—C12—H12B | 109.5 | H32A—C32—H32B | 109.5 |
N4—C12—H12C | 109.5 | N8—C32—H32C | 109.5 |
H12A—C12—H12C | 109.5 | H32A—C32—H32C | 109.5 |
H12B—C12—H12C | 109.5 | H32B—C32—H32C | 109.5 |
N4—C13—H13A | 109.5 | N8—C33—H33A | 109.5 |
N4—C13—H13B | 109.5 | N8—C33—H33B | 109.5 |
H13A—C13—H13B | 109.5 | H33A—C33—H33B | 109.5 |
N4—C13—H13C | 109.5 | N8—C33—H33C | 109.5 |
H13A—C13—H13C | 109.5 | H33A—C33—H33C | 109.5 |
H13B—C13—H13C | 109.5 | H33B—C33—H33C | 109.5 |
O2—C14—N3 | 129.5 (3) | O4—C34—N7 | 129.7 (3) |
O2—C14—C15 | 114.5 (3) | O4—C34—C35 | 114.2 (3) |
N3—C14—C15 | 116.0 (3) | N7—C34—C35 | 116.1 (3) |
C20—C15—C16 | 119.0 (3) | C40—C35—C36 | 118.9 (3) |
C20—C15—C14 | 119.8 (3) | C40—C35—C34 | 119.9 (3) |
C16—C15—C14 | 121.3 (3) | C36—C35—C34 | 121.3 (3) |
C15—C16—C17 | 120.7 (3) | C37—C36—C35 | 119.9 (4) |
C15—C16—H16A | 119.7 | C37—C36—H36A | 120.1 |
C17—C16—H16A | 119.7 | C35—C36—H36A | 120.1 |
C18—C17—C16 | 118.8 (3) | C38—C37—C36 | 119.6 (4) |
C18—C17—H17A | 120.6 | C38—C37—H37A | 120.2 |
C16—C17—H17A | 120.6 | C36—C37—H37A | 120.2 |
C17—C18—C19 | 121.7 (3) | C37—C38—C39 | 122.0 (3) |
C17—C18—Br2 | 120.1 (3) | C37—C38—Br4 | 119.3 (3) |
C19—C18—Br2 | 118.1 (3) | C39—C38—Br4 | 118.7 (3) |
C20—C19—C18 | 118.5 (3) | C38—C39—C40 | 118.0 (4) |
C20—C19—H19A | 120.8 | C38—C39—H39A | 121.0 |
C18—C19—H19A | 120.8 | C40—C39—H39A | 121.0 |
C15—C20—C19 | 121.4 (3) | C35—C40—C39 | 121.6 (3) |
C15—C20—H20A | 119.3 | C35—C40—H40A | 119.2 |
C19—C20—H20A | 119.3 | C39—C40—H40A | 119.2 |
O1—Cu1—S1—C1 | 22.70 (14) | O3—Cu2—S3—C21 | −11.88 (15) |
S2—Cu1—S1—C1 | −153.87 (12) | S4—Cu2—S3—C21 | 166.49 (13) |
O2—Cu1—S2—C11 | 16.75 (15) | O4—Cu2—S4—C31 | −4.72 (15) |
S1—Cu1—S2—C11 | −159.88 (13) | S3—Cu2—S4—C31 | 174.00 (13) |
O2—Cu1—O1—C4 | 161.0 (3) | O4—Cu2—O3—C24 | −173.4 (3) |
S1—Cu1—O1—C4 | −22.5 (3) | S3—Cu2—O3—C24 | 7.9 (3) |
O1—Cu1—O2—C14 | 159.3 (3) | O3—Cu2—O4—C34 | −176.0 (4) |
S2—Cu1—O2—C14 | −24.2 (3) | S4—Cu2—O4—C34 | 5.6 (3) |
C2—N2—C1—N1 | 178.8 (3) | C24—N5—C21—N6 | 177.0 (3) |
C3—N2—C1—N1 | 0.0 (5) | C24—N5—C21—S3 | −5.8 (5) |
C2—N2—C1—S1 | −3.6 (4) | C22—N6—C21—N5 | −0.2 (5) |
C3—N2—C1—S1 | 177.6 (3) | C23—N6—C21—N5 | 178.8 (3) |
C4—N1—C1—N2 | 179.7 (3) | C22—N6—C21—S3 | −177.8 (3) |
C4—N1—C1—S1 | 2.5 (5) | C23—N6—C21—S3 | 1.2 (5) |
Cu1—S1—C1—N2 | 162.9 (2) | Cu2—S3—C21—N5 | 14.2 (4) |
Cu1—S1—C1—N1 | −19.8 (3) | Cu2—S3—C21—N6 | −168.6 (2) |
Cu1—O1—C4—N1 | 7.8 (6) | Cu2—O3—C24—N5 | 0.8 (6) |
Cu1—O1—C4—C5 | −170.2 (2) | Cu2—O3—C24—C25 | 178.3 (2) |
C1—N1—C4—O1 | 7.7 (6) | C21—N5—C24—O3 | −4.0 (6) |
C1—N1—C4—C5 | −174.3 (3) | C21—N5—C24—C25 | 178.5 (3) |
O1—C4—C5—C10 | −8.1 (5) | O3—C24—C25—C30 | −175.4 (3) |
N1—C4—C5—C10 | 173.6 (3) | N5—C24—C25—C30 | 2.5 (5) |
O1—C4—C5—C6 | 170.5 (3) | O3—C24—C25—C26 | 2.7 (5) |
N1—C4—C5—C6 | −7.9 (5) | N5—C24—C25—C26 | −179.4 (3) |
C10—C5—C6—C7 | 0.3 (5) | C30—C25—C26—C27 | 1.4 (5) |
C4—C5—C6—C7 | −178.3 (3) | C24—C25—C26—C27 | −176.7 (3) |
C5—C6—C7—C8 | −1.2 (5) | C25—C26—C27—C28 | −0.6 (5) |
C6—C7—C8—C9 | 1.4 (5) | C26—C27—C28—C29 | −0.6 (6) |
C6—C7—C8—Br1 | −177.2 (3) | C26—C27—C28—Br3 | 177.2 (3) |
C7—C8—C9—C10 | −0.8 (5) | C27—C28—C29—C30 | 1.1 (6) |
Br1—C8—C9—C10 | 177.9 (3) | Br3—C28—C29—C30 | −176.8 (3) |
C6—C5—C10—C9 | 0.4 (5) | C26—C25—C30—C29 | −1.0 (5) |
C4—C5—C10—C9 | 179.0 (3) | C24—C25—C30—C29 | 177.1 (3) |
C8—C9—C10—C5 | −0.2 (5) | C28—C29—C30—C25 | −0.3 (6) |
C13—N4—C11—N3 | 179.3 (3) | C33—N8—C31—N7 | −177.8 (3) |
C12—N4—C11—N3 | −0.4 (5) | C32—N8—C31—N7 | 2.2 (5) |
C13—N4—C11—S2 | −0.8 (5) | C33—N8—C31—S4 | 1.4 (5) |
C12—N4—C11—S2 | 179.6 (3) | C32—N8—C31—S4 | −178.5 (3) |
C14—N3—C11—N4 | 175.5 (3) | C34—N7—C31—N8 | 178.5 (3) |
C14—N3—C11—S2 | −4.5 (5) | C34—N7—C31—S4 | −0.6 (5) |
Cu1—S2—C11—N4 | 171.5 (2) | Cu2—S4—C31—N8 | −175.2 (2) |
Cu1—S2—C11—N3 | −8.5 (3) | Cu2—S4—C31—N7 | 3.8 (4) |
Cu1—O2—C14—N3 | 16.2 (6) | Cu2—O4—C34—N7 | −3.4 (6) |
Cu1—O2—C14—C15 | −164.1 (2) | Cu2—O4—C34—C35 | 176.1 (2) |
C11—N3—C14—O2 | 3.5 (6) | C31—N7—C34—O4 | −0.5 (6) |
C11—N3—C14—C15 | −176.3 (3) | C31—N7—C34—C35 | −179.9 (3) |
O2—C14—C15—C20 | 3.8 (5) | O4—C34—C35—C40 | 1.1 (5) |
N3—C14—C15—C20 | −176.5 (3) | N7—C34—C35—C40 | −179.3 (3) |
O2—C14—C15—C16 | −177.1 (3) | O4—C34—C35—C36 | −178.9 (3) |
N3—C14—C15—C16 | 2.7 (5) | N7—C34—C35—C36 | 0.7 (5) |
C20—C15—C16—C17 | 0.2 (6) | C40—C35—C36—C37 | −0.7 (6) |
C14—C15—C16—C17 | −179.0 (3) | C34—C35—C36—C37 | 179.3 (3) |
C15—C16—C17—C18 | −0.6 (6) | C35—C36—C37—C38 | 0.3 (6) |
C16—C17—C18—C19 | 0.5 (6) | C36—C37—C38—C39 | 0.1 (6) |
C16—C17—C18—Br2 | −179.8 (3) | C36—C37—C38—Br4 | −178.0 (3) |
C17—C18—C19—C20 | 0.0 (6) | C37—C38—C39—C40 | −0.1 (6) |
Br2—C18—C19—C20 | −179.7 (3) | Br4—C38—C39—C40 | 178.0 (3) |
C16—C15—C20—C19 | 0.4 (5) | C36—C35—C40—C39 | 0.7 (6) |
C14—C15—C20—C19 | 179.6 (3) | C34—C35—C40—C39 | −179.3 (3) |
C18—C19—C20—C15 | −0.5 (6) | C38—C39—C40—C35 | −0.3 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13C···Br2i | 0.98 | 2.92 | 3.809 (4) | 150 |
C19—H19A···Br4ii | 0.95 | 2.91 | 3.858 (4) | 174 |
C27—H27A···Br1iii | 0.95 | 2.90 | 3.849 (4) | 176 |
C37—H37A···Br3iv | 0.95 | 2.93 | 3.845 (4) | 163 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) x, y, z−1; (iv) x+1, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | [Cu(C10H10BrN2OS)2] |
Mr | 635.88 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 120 |
a, b, c (Å) | 9.1780 (11), 11.0028 (13), 23.241 (3) |
α, β, γ (°) | 94.857 (2), 96.144 (3), 95.095 (2) |
V (Å3) | 2313.7 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 4.60 |
Crystal size (mm) | 0.28 × 0.21 × 0.12 |
Data collection | |
Diffractometer | Bruker SMART APEX diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.359, 0.608 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20433, 10926, 8446 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.658 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.117, 1.00 |
No. of reflections | 10926 |
No. of parameters | 567 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.98, −0.84 |
Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), SHELXTL (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), publCIF (Westrip, 2010) and Mercury (Macrae et al., 2006).
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13C···Br2i | 0.98 | 2.92 | 3.809 (4) | 150 |
C19—H19A···Br4ii | 0.95 | 2.91 | 3.858 (4) | 174 |
C27—H27A···Br1iii | 0.95 | 2.90 | 3.849 (4) | 176 |
C37—H37A···Br3iv | 0.95 | 2.93 | 3.845 (4) | 163 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y, z+1; (iii) x, y, z−1; (iv) x+1, y+1, z. |
Acknowledgements
This work was supported by Mersin University Research Fund [project Nos. BAP-ECZ-F-TBB-(HA) 2004–3 and BAP-FEF-KB-(NK) 2006–3].
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
The ability of thiourea derivatives to complex with transition metal cations is well known (Arslan et al., 2009; Avşar et al., 2002, Arslan et al., 2006). Thioureas are able to coordinate a range of metal centers as neutral ligands, monoanions or dianions (Sacht et al., 2000; Henderson et al., 2002). The oxygen, nitrogen and sulfur donors of thioureas provide a multitude of bonding possibilities.
In view of this information and in continuation of our research into the thiourea derivatives, we synthesized and characterized a series of substituted thiourea derivatives (Binzet et al., 2009; Arslan et al., 2003; Avşar et al., 2003; Emen et al., 2005; Mansuroğlu et al., 2008). The title compound, cis-bis(N,N-dimethyl-N'-4-bromobenzoylthioureato)copper(II), (I), is another example of our synthesized thiourea derivatives that contains both aryl and alkyl groups.
There are two similar molecules in the asymmetric unit, so discussion will primarily focus on one of these independent molecules; see Fig. 1 and 2 for a view of one of the two independent molecules. There is very little difference between the bond lengths and angles of these molecules. The crystal structure of the title compound confirms N,N-dimethyl-N'-4-bromobenzoylthiourea ligand is a bidentate chelating ligand, coordinating to the copper atom through the thiocarbonyl and carbonyl groups. The central copper atom shows slightly distorted square-planar coordination and the sulfur atoms are in a cis configuration. The maximum deviations from the S2O2 mean plane are 0.065 (3) Å for oxygen, 0.054 (1) Å for sulfur and 0.000 (1) Å for copper. The Cu1/S2/C11/N3/C14/O2 ring adopts an envelope conformation with puckering parameter Q = 0.2593 (19) Å, θ = 121.0 (7)°, ϕ = 181.3 (8) ° (Cremer & Pople, 1975). Cu—O [average 1.857 (3) Å] and Cu—S [average 2.1442 (10) Å] bond lengths are in the expected ranges. The dihedral angle between these chelate planes of 6.23 (10)° indicates slight distortion from square planar towards tetrahedral geometry. C–O, C–S and C–N bond lengths of the complex suggest considerable electronic delocalization in the chelate rings. The bond lengths of the carbonyl O1–C4 1.265 (4) Å; O2–C14 1.270 (4) Å and thiocarbonyl S1–C1 1.738 (4) Å; S2–C11 1.734 (4) Å groups lie between those for double and single bonds, similar to related structures (Arslan et al. 2003, 2006; Avşar et al., 2003; Binzet et al., 2009), while both C–O and C–S bond lengths are typical of double bonds in the free ligand. The other bond lengths in title compound show normal values.