{N,N′-[2,2′-(Ethane-1,2-diyldisulfanediyl)di-o-phenyl­ene]bis­(quinoline-2-carboxamidato)}copper(II)

Meghdadi, S.; Mirkhani, V.; Ford, P.C.

doi:10.1107/S1600536811019581

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m820-m821

doi:10.1107/S1600536811019581

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{N,N′-[2,2′-(Ethane-1,2-diyldisulfanediyl)di-o-phenylene]bis(quinoline-2-carboxamidato)}copper(II)

Soraia Meghdadi,^a ^* Valiollah Mirkhani ^a and Peter C. Ford ^b

^aDepartment of Chemistry, University of Isfahan, Isfahan 81746-73441, Iran, and ^bDepartment of Chemistry and Biochemistry, University of California, Santa Barbara, California, 93106, USA
^*Correspondence e-mail: smeghdad@cc.iut.ac.ir

(Received 8 May 2011; accepted 24 May 2011; online 28 May 2011)

In the title compound, [Cu(C₃₄H₂₄N₄O₂S₂)] or [Cu(bqdapte)], where H₂bqdapte is 1,2-{bis[2-(quinoline-2-carboxamido)phenyl]sulfanyl}ethane, the Cu^II ion is coordinated to the dianionic hexadentate bqdapte²⁻ ligand by two amide and two quinoline N atoms and two thioether S atoms. In the observed conformation of the hexadentate ligand, the quinoline rings attain positions related by a twofold axis. The Cu atom displays a Jahn–Teller-distorted octahedral CuN₄S₂ geometry axially compressed along the two trans-configured Cu—N_amidate bonds.

Related literature

For general background to the applications of transition metal complexes of hybrid N,S-donor ligands, see: Kouroulis et al. (2009 ); Lee et al. (2007 ); Ronson et al. (2006 ); Sarkar et al. (2009 ); Tavacoli et al. (2003 ); Xie et al. (2005 ). For related structures, see: Kouroulis et al. (2009); Sarkar et al. (2009); Singh & Mukherjee (2005 ); Sunatsuki et al. (1998 ); Zhang et al. (2004 ). For the synthesis of the ligand see: Meghdadi et al. (2011 ).

Experimental

Crystal data

[Cu(C₃₄H₂₄N₄O₂S₂)]
M_r = 648.23
Orthorhombic, P c c n
a = 11.4124 (15) Å
b = 13.5097 (18) Å
c = 18.606 (2) Å
V = 2868.6 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.95 mm⁻¹
T = 150 K
0.30 × 0.25 × 0.08 mm

Data collection

Bruker SMART 100 diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2003 ) T_min = 0.770, T_max = 0.927
21464 measured reflections
2926 independent reflections
2467 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.119
S = 1.22
2926 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 0.83 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019581/qk2010sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019581/qk2010Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of transition metal complexes with flexible hybrid N,S-donor ligands has been the focus of growing attention (Sarkar et al. 2009) due to their application in designing new molecular architectures (Ronson et al., 2006; Tavacoli et al.., 2003; Xie et al.., 2005) and in bioinorganic chemistry (Kouroulis et al. 2009; Lee et al., 2007). Many of these efforts have been devoted to the design and synthesis of new caboxamide ligands (Kouroulis et al. 2009; Singh & Mukherjee 2005; Sunatsuki et al., 1998; Zhang et al., 2004). The bioinorganic relevance of copper and its crucial role in many biological and catalytic functions have stimulated efforts towards the design, synthesis, and characterization of copper complexes as models for providing better understanding of biological systems and for the development of efficient catalysts (Lee et al., 2007; Zhang et al., 2004). In continuation of our studies on carboxamido metal complexes, we herein report the synthesis and structure of the title compound, [Cu(C₃₄H₂₄N₄O₂S₂)], (I), and make a brief comparison with reported structures.

The structure of complex (I), and the atomic numbering used, is shown in Fig. 1. The Cu(II) ion displays a Jahn-Teller distorted octahedral CuN₄S₂ geometry arising from the hexadentate thiocarboxamido ligand. This complex has a 2-fold axis passing through Cu and the midpoint of C17 and its symmetry related atom. Two quinoline nitrogen, two deprotonated amide nitrogen, and two thioether sulfur bind copper(II) in cis, trans, and cis orientations. The geometric parameters are listed below in the supplementary materials. The angles at the metal center between cis-positioned donor pairs span the range 80.23 (7) - 105.76 (8)° and are close to those reported for related complexes (Singh & Mukherjee, 2005; Zhang et al., 2004). The three trans angles, N1—Cu—N1ⁱ 171.46 (10)°, N2—Cu—S 163.79 (5)°, and N2ⁱ—Cu—Si 163.79 (5)°, deviate significantly from the ideal value of 180° for a regular octahedral structure. This is presumably due to the structural demands imparted by the hexadentate ligand. The dimethylene bridge of the five-membered CuS₂C₂ ring has gauche conformation. The equatorial plane is occupied by two N atoms from quinoline moieties at longer Cu–N distances [2.183 (2) Å] and two thioether sulfur atoms [2.523 (1) Å]. The axial positions are occupied by the two amido nitrogen atoms at shorter Cu–N1 distances [1.956 (2) Å]. This Cu–N1 bond distance lies in the range of normal values for copper(II) to deprotonated amido nitrogen bond distances (Sunatsuki et al., 1998). On the other hand, Cu–N2 bond distance is longer than normal value of 1.96–2.08 Å for the copper(II) to pyridyl nitrogen in related complexes. (Singh & Mukherjee, 2005; Sunatsuki et al., 1998; Zhang et al., 2004). In agreement with findings on a pair of analogous Cu and Ni complexes with pyridine replacing quinoline in the bqdapte ligand (Sunatsuki et al., 1998), the coordination of the copper(II) ion in the title compound can be described as a Jahn-Teller distorted axially compressed (N1 and N1ⁱ) and equatorially elongated octahedron (N2, S, N2ⁱ, Sⁱ).

Related literature top

For general background to the applications of transition metal complexes of hybrid N,S-donor ligands, see: Kouroulis et al. (2009); Lee et al. (2007); Ronson et al. (2006); Sarkar et al. (2009); Tavacoli et al. (2003); Xie et al. (2005). For related structures, see: Kouroulis et al. (2009); Sarkar et al. (2009); Singh & Mukherjee (2005); Sunatsuki et al. (1998); Zhang et al. (2004). For the synthesis of the ligand see: Meghdadi et al. (2011).

Experimental top

The ligand 1,4-bis[o-(quinoline-2-carboxamidophenyl)]-1,4-dithiobutane (H₂bqctb) was prepared according to a general method reported elsewhere (Meghdadi et al., 2011) by the reaction of quinaldic acid with 1,2-di(o-aminophenylthio)ethane (dapte) in the presence of triphenyl phosphite (TPP) and in tetrabutylammonium bromide (TBAB) as the reaction media.

The title complex was prepared as follows. To a stirring solution of H₂bqctb (58.6 mg, 0.1 mmol) in dichloromethane (20 ml) was added a solution of Cu(CH₃COO)₂.H₂O (20 mg, 0.1 mmol) in methanol (20 ml), and the mixture was stirred for 4 h. The final reaction mixture was filtered and the filtrate was left undisturbed for 24 h. Bright green crystals suitable for X-ray crystallography were obtained by slow evaporation of the filtrate at room temperature. The crystals were filtered off and washed with cold diethyl ether-dichloromethane (9/1), and dried under vacuum. Yield: 71%.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The ORTEP drawing of (I), with atom labeling scheme. Displacement ellipsoids are drawn at 50% probability level.

{N,N'-[2,2'-(Ethane-1,2-diyldisulfanediyl)di-o- phenylene]bis(quinoline-2-carboxamidato)}copper(II) top

Crystal data top

[Cu(C₃₄H₂₄N₄O₂S₂)]	D_x = 1.501 Mg m⁻³
M_r = 648.23	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 118 reflections
a = 11.4124 (15) Å	θ = 17.8–27.3°
b = 13.5097 (18) Å	µ = 0.95 mm⁻¹
c = 18.606 (2) Å	T = 150 K
V = 2868.6 (7) Å³	Plate, green
Z = 4	0.3 × 0.25 × 0.08 mm
F(000) = 1332

Data collection top

Bruker SMART 100 diffractometer	2926 independent reflections
Radiation source: fine-focus sealed tube	2467 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ω scans	θ_max = 26.4°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −14→14
T_min = 0.770, T_max = 0.927	k = −16→15
21464 measured reflections	l = −23→23

Refinement top

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.22	w = 1/[σ²(F_o²) + (0.072P)²] where P = (F_o² + 2F_c²)/3
2926 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.83 e Å⁻³
0 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

[Cu(C₃₄H₂₄N₄O₂S₂)]	V = 2868.6 (7) Å³
M_r = 648.23	Z = 4
Orthorhombic, Pccn	Mo Kα radiation
a = 11.4124 (15) Å	µ = 0.95 mm⁻¹
b = 13.5097 (18) Å	T = 150 K
c = 18.606 (2) Å	0.3 × 0.25 × 0.08 mm

Data collection top

Bruker SMART 100 diffractometer	2926 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	2467 reflections with I > 2σ(I)
T_min = 0.770, T_max = 0.927	R_int = 0.040
21464 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.22	Δρ_max = 0.83 e Å⁻³
2926 reflections	Δρ_min = −0.40 e Å⁻³
195 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.95359 (19)	0.63312 (18)	0.40463 (12)	0.0287 (5)
C2	0.97185 (18)	0.72050 (18)	0.45446 (11)	0.0254 (5)
C3	1.07936 (19)	0.72879 (19)	0.49149 (13)	0.0324 (6)
H3	1.1395	0.6837	0.4832	0.039*
C4	1.09359 (19)	0.80390 (19)	0.53956 (12)	0.0326 (6)
H4	1.1642	0.8112	0.5639	0.039*
C5	1.00127 (18)	0.87021 (17)	0.55221 (11)	0.0267 (5)
C6	1.0075 (2)	0.9476 (2)	0.60300 (13)	0.0329 (6)
H6	1.0766	0.9576	0.6285	0.040*
C7	0.9143 (2)	1.0077 (2)	0.61517 (12)	0.0336 (6)
H7	0.9200	1.0579	0.6492	0.040*
C8	0.8095 (2)	0.99472 (18)	0.57677 (13)	0.0320 (5)
H8	0.7460	1.0360	0.5858	0.038*
C9	0.80010 (19)	0.92180 (18)	0.52621 (12)	0.0284 (5)
H9	0.7308	0.9146	0.5004	0.034*
C10	0.89525 (18)	0.85719 (17)	0.51284 (11)	0.0236 (5)
C11	0.81073 (18)	0.54899 (17)	0.33282 (11)	0.0260 (5)
C12	0.85951 (19)	0.45376 (19)	0.33824 (13)	0.0321 (5)
H12	0.9200	0.4426	0.3707	0.039*
C13	0.8195 (2)	0.37658 (19)	0.29635 (13)	0.0358 (6)
H13	0.8535	0.3143	0.3010	0.043*
C14	0.7295 (2)	0.39057 (19)	0.24748 (13)	0.0340 (6)
H14	0.7045	0.3385	0.2186	0.041*
C15	0.6777 (2)	0.48159 (18)	0.24211 (12)	0.0309 (5)
H15	0.6162	0.4909	0.2100	0.037*
C16	0.71616 (19)	0.56053 (18)	0.28432 (12)	0.0267 (5)
C17	0.6849 (2)	0.7377 (2)	0.20459 (13)	0.0427 (7)
H17A	0.6677	0.6982	0.1623	0.051*
H17B	0.6410	0.7989	0.2005	0.051*
Cu	0.7500	0.7500	0.38326 (2)	0.02369 (16)
N1	0.84546 (16)	0.63022 (15)	0.37545 (9)	0.0242 (4)
N2	0.88397 (15)	0.78305 (15)	0.46349 (9)	0.0245 (4)
O	1.03533 (14)	0.57507 (15)	0.39668 (10)	0.0433 (5)
S	0.63335 (5)	0.67137 (5)	0.28325 (3)	0.03301 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0220 (11)	0.0413 (14)	0.0229 (11)	0.0030 (10)	0.0022 (9)	−0.0047 (10)
C2	0.0188 (10)	0.0374 (12)	0.0199 (10)	0.0012 (9)	−0.0004 (8)	−0.0011 (9)
C3	0.0200 (11)	0.0451 (14)	0.0321 (13)	0.0074 (10)	−0.0029 (9)	−0.0080 (11)
C4	0.0188 (11)	0.0490 (16)	0.0300 (12)	0.0028 (10)	−0.0053 (9)	−0.0047 (11)
C5	0.0225 (11)	0.0362 (13)	0.0212 (11)	0.0010 (9)	0.0002 (9)	0.0008 (9)
C6	0.0254 (12)	0.0450 (15)	0.0283 (12)	−0.0028 (10)	−0.0032 (9)	−0.0056 (11)
C7	0.0346 (13)	0.0385 (14)	0.0276 (12)	−0.0005 (11)	0.0019 (9)	−0.0086 (10)
C8	0.0284 (12)	0.0345 (13)	0.0331 (13)	0.0059 (10)	0.0062 (10)	−0.0002 (10)
C9	0.0228 (11)	0.0370 (14)	0.0255 (11)	0.0042 (10)	0.0026 (9)	0.0017 (10)
C10	0.0206 (10)	0.0320 (12)	0.0180 (10)	0.0008 (9)	0.0042 (8)	0.0027 (9)
C11	0.0222 (10)	0.0341 (13)	0.0216 (11)	−0.0017 (9)	0.0040 (9)	−0.0018 (9)
C12	0.0274 (11)	0.0410 (14)	0.0280 (12)	−0.0023 (10)	0.0020 (10)	0.0032 (11)
C13	0.0402 (13)	0.0314 (14)	0.0359 (13)	−0.0009 (11)	0.0079 (11)	0.0008 (10)
C14	0.0420 (14)	0.0330 (14)	0.0269 (12)	−0.0085 (11)	0.0052 (10)	−0.0045 (10)
C15	0.0327 (12)	0.0388 (14)	0.0212 (11)	−0.0093 (10)	0.0022 (9)	−0.0009 (10)
C16	0.0244 (10)	0.0352 (13)	0.0206 (11)	−0.0021 (9)	0.0028 (9)	−0.0006 (9)
C17	0.0633 (18)	0.0398 (16)	0.0249 (13)	0.0066 (13)	−0.0162 (12)	−0.0024 (10)
Cu	0.0172 (2)	0.0340 (3)	0.0199 (2)	−0.00048 (15)	0.000	0.000
N1	0.0192 (9)	0.0337 (11)	0.0199 (9)	0.0004 (8)	0.0008 (7)	−0.0029 (8)
N2	0.0174 (8)	0.0361 (10)	0.0201 (9)	0.0009 (8)	0.0012 (7)	0.0021 (8)
O	0.0219 (9)	0.0598 (13)	0.0481 (11)	0.0127 (8)	−0.0052 (8)	−0.0262 (9)
S	0.0244 (3)	0.0392 (4)	0.0354 (4)	0.0007 (2)	−0.0049 (2)	−0.0076 (3)

Geometric parameters (Å, º) top

C1—O	1.228 (3)	C11—N1	1.411 (3)
C1—N1	1.349 (3)	C11—C16	1.415 (3)
C1—C2	1.515 (3)	C12—C13	1.379 (4)
C2—N2	1.322 (3)	C12—H12	0.9300
C2—C3	1.412 (3)	C13—C14	1.385 (4)
C3—C4	1.362 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.368 (4)
C4—C5	1.403 (3)	C14—H14	0.9300
C4—H4	0.9300	C15—C16	1.395 (3)
C5—C6	1.411 (3)	C15—H15	0.9300
C5—C10	1.425 (3)	C16—S	1.771 (2)
C6—C7	1.357 (3)	C17—C17ⁱ	1.523 (6)
C6—H6	0.9300	C17—S	1.814 (3)
C7—C8	1.405 (3)	C17—H17A	0.9700
C7—H7	0.9300	C17—H17B	0.9700
C8—C9	1.366 (3)	Cu—N1ⁱ	1.9561 (19)
C8—H8	0.9300	Cu—N1	1.956 (2)
C9—C10	1.415 (3)	Cu—N2	2.1830 (18)
C9—H9	0.9300	Cu—N2ⁱ	2.1830 (18)
C10—N2	1.365 (3)	Cu—S	2.5225 (7)
C11—C12	1.405 (3)	Cu—Sⁱ	2.5225 (7)

O—C1—N1	128.9 (2)	C15—C14—C13	119.4 (2)
O—C1—C2	117.83 (19)	C15—C14—H14	120.3
N1—C1—C2	113.24 (19)	C13—C14—H14	120.3
N2—C2—C3	123.1 (2)	C14—C15—C16	120.6 (2)
N2—C2—C1	118.12 (19)	C14—C15—H15	119.7
C3—C2—C1	118.7 (2)	C16—C15—H15	119.7
C4—C3—C2	118.9 (2)	C15—C16—C11	121.0 (2)
C4—C3—H3	120.6	C15—C16—S	118.16 (17)
C2—C3—H3	120.6	C11—C16—S	120.48 (17)
C3—C4—C5	119.7 (2)	C17ⁱ—C17—S	115.10 (14)
C3—C4—H4	120.1	C17ⁱ—C17—H17A	108.5
C5—C4—H4	120.1	S—C17—H17A	108.5
C4—C5—C6	123.2 (2)	C17ⁱ—C17—H17B	108.5
C4—C5—C10	118.2 (2)	S—C17—H17B	108.5
C6—C5—C10	118.6 (2)	H17A—C17—H17B	107.5
C7—C6—C5	121.0 (2)	N1ⁱ—Cu—N1	171.48 (10)
C7—C6—H6	119.5	N1ⁱ—Cu—N2	105.76 (8)
C5—C6—H6	119.5	N1—Cu—N2	80.21 (7)
C6—C7—C8	120.5 (2)	N1ⁱ—Cu—N2ⁱ	80.21 (7)
C6—C7—H7	119.7	N1—Cu—N2ⁱ	105.76 (8)
C8—C7—H7	119.7	N2—Cu—N2ⁱ	93.71 (9)
C9—C8—C7	120.5 (2)	N1ⁱ—Cu—S	89.98 (6)
C9—C8—H8	119.8	N1—Cu—S	83.73 (5)
C7—C8—H8	119.8	N2—Cu—S	163.78 (5)
C8—C9—C10	120.4 (2)	N2ⁱ—Cu—S	92.79 (5)
C8—C9—H9	119.8	N1ⁱ—Cu—Sⁱ	83.73 (5)
C10—C9—H9	119.8	N1—Cu—Sⁱ	89.98 (6)
N2—C10—C9	119.90 (19)	N2—Cu—Sⁱ	92.79 (5)
N2—C10—C5	121.08 (19)	N2ⁱ—Cu—Sⁱ	163.78 (5)
C9—C10—C5	119.0 (2)	S—Cu—Sⁱ	84.93 (3)
C12—C11—N1	124.1 (2)	C1—N1—C11	120.39 (19)
C12—C11—C16	116.7 (2)	C1—N1—Cu	117.11 (16)
N1—C11—C16	119.1 (2)	C11—N1—Cu	121.92 (14)
C13—C12—C11	121.4 (2)	C2—N2—C10	118.88 (18)
C13—C12—H12	119.3	C2—N2—Cu	108.28 (15)
C11—C12—H12	119.3	C10—N2—Cu	132.55 (14)
C12—C13—C14	120.9 (2)	C16—S—C17	104.70 (12)
C12—C13—H13	119.6	C16—S—Cu	93.79 (7)
C14—C13—H13	119.6	C17—S—Cu	102.48 (9)

O—C1—C2—N2	−179.7 (2)	S—Cu—N1—C1	162.05 (16)
N1—C1—C2—N2	−0.6 (3)	Sⁱ—Cu—N1—C1	77.15 (15)
O—C1—C2—C3	−2.6 (3)	N2—Cu—N1—C11	173.02 (17)
N1—C1—C2—C3	176.5 (2)	N2ⁱ—Cu—N1—C11	81.90 (16)
N2—C2—C3—C4	0.8 (4)	S—Cu—N1—C11	−9.24 (15)
C1—C2—C3—C4	−176.1 (2)	Sⁱ—Cu—N1—C11	−94.14 (16)
C2—C3—C4—C5	1.0 (4)	C3—C2—N2—C10	−2.6 (3)
C3—C4—C5—C6	177.6 (2)	C1—C2—N2—C10	174.38 (19)
C3—C4—C5—C10	−1.0 (3)	C3—C2—N2—Cu	171.95 (19)
C4—C5—C6—C7	−177.6 (2)	C1—C2—N2—Cu	−11.1 (2)
C10—C5—C6—C7	1.0 (4)	C9—C10—N2—C2	−176.6 (2)
C5—C6—C7—C8	−0.6 (4)	C5—C10—N2—C2	2.5 (3)
C6—C7—C8—C9	−0.5 (4)	C9—C10—N2—Cu	10.4 (3)
C7—C8—C9—C10	1.2 (4)	C5—C10—N2—Cu	−170.41 (15)
C8—C9—C10—N2	178.4 (2)	N1ⁱ—Cu—N2—C2	−159.59 (15)
C8—C9—C10—C5	−0.8 (3)	N1—Cu—N2—C2	14.17 (15)
C4—C5—C10—N2	−0.8 (3)	N2ⁱ—Cu—N2—C2	119.54 (17)
C6—C5—C10—N2	−179.5 (2)	S—Cu—N2—C2	6.1 (3)
C4—C5—C10—C9	178.4 (2)	Sⁱ—Cu—N2—C2	−75.33 (15)
C6—C5—C10—C9	−0.3 (3)	N1ⁱ—Cu—N2—C10	13.9 (2)
N1—C11—C12—C13	178.2 (2)	N1—Cu—N2—C10	−172.3 (2)
C16—C11—C12—C13	2.2 (3)	N2ⁱ—Cu—N2—C10	−66.97 (17)
C11—C12—C13—C14	−0.1 (4)	S—Cu—N2—C10	179.59 (13)
C12—C13—C14—C15	−1.7 (4)	Sⁱ—Cu—N2—C10	98.16 (19)
C13—C14—C15—C16	1.2 (3)	C15—C16—S—C17	−83.65 (19)
C14—C15—C16—C11	1.0 (3)	C11—C16—S—C17	103.38 (19)
C14—C15—C16—S	−171.92 (18)	C15—C16—S—Cu	172.39 (17)
C12—C11—C16—C15	−2.7 (3)	C11—C16—S—Cu	−0.59 (18)
N1—C11—C16—C15	−178.84 (18)	C17ⁱ—C17—S—C16	−59.6 (3)
C12—C11—C16—S	170.09 (16)	C17ⁱ—C17—S—Cu	37.8 (3)
N1—C11—C16—S	−6.1 (3)	N1ⁱ—Cu—S—C16	178.82 (9)
O—C1—N1—C11	4.6 (4)	N1—Cu—S—C16	4.58 (9)
C2—C1—N1—C11	−174.42 (18)	N2—Cu—S—C16	12.6 (2)
O—C1—N1—Cu	−166.8 (2)	N2ⁱ—Cu—S—C16	−100.98 (9)
C2—C1—N1—Cu	14.1 (2)	Sⁱ—Cu—S—C16	95.11 (7)
C12—C11—N1—C1	24.9 (3)	N1ⁱ—Cu—S—C17	72.85 (11)
C16—C11—N1—C1	−159.3 (2)	N1—Cu—S—C17	−101.39 (11)
C12—C11—N1—Cu	−164.14 (16)	N2—Cu—S—C17	−93.4 (2)
C16—C11—N1—Cu	11.7 (3)	N2ⁱ—Cu—S—C17	153.05 (11)
N2—Cu—N1—C1	−15.69 (15)	Sⁱ—Cu—S—C17	−10.85 (9)
N2ⁱ—Cu—N1—C1	−106.81 (16)

Symmetry code: (i) −x+3/2, −y+3/2, z.

Experimental details

Crystal data
Chemical formula	[Cu(C₃₄H₂₄N₄O₂S₂)]
M_r	648.23
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	150
a, b, c (Å)	11.4124 (15), 13.5097 (18), 18.606 (2)
V (Å³)	2868.6 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.95
Crystal size (mm)	0.3 × 0.25 × 0.08

Data collection
Diffractometer	Bruker SMART 100 diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.770, 0.927
No. of measured, independent and observed [I > 2σ(I)] reflections	21464, 2926, 2467
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.119, 1.22
No. of reflections	2926
No. of parameters	195
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.83, −0.40

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

Partial support of this work by the Research Council of the University of Isfahan is gratefully acknowledged. Also acknowledged is partial support from the US National Science Foundation grant (NSF-CHE-0749524) to PCF.

References

Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kouroulis, K. N., Hadjikakou, S. K., Kourkoumelis, N., Kubicki, M., Male, L., Hursthouse, M., Skoulika, S., Metsios, A. K., Tyurin, V. Y., Dolganov, A. V., Milaeva, E. R. & Hadjiliadis, N. (2009). Dalton Trans. pp. 10446–10456. CrossRef Google Scholar
Lee, D.-H., Hatcher, L. Q., Vance, M. A., Sarangi, R., Milligan, A. E., Narducci Sarjeant, A. A., Incarvito, C. D., Rheingold, A. L., Hodgson, K. O., Hedman, B., Solomon, E. I. & Karlin, K. D. (2007). Inorg. Chem. 46, 6056–6068. Web of Science CrossRef PubMed CAS Google Scholar
Meghdadi, S., Mirkhani, V. & Ford, P. C. (2011). Synth. Commun. In the press. Google Scholar
Ronson, T. K., Adams, H. & Ward, M. D. (2006). CrystEngComm, 8, 497–501. CrossRef CAS Google Scholar
Sarkar, S., Patra, A., Drew, M. G. B., Zangrando, E. & Chattopadhyay, P. (2009). Polyhedron, 28, 1–6. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, A. K. & Mukherjee, R. (2005). Inorg. Chem. 44, 5813–5819. Web of Science CrossRef PubMed CAS Google Scholar
Sunatsuki, Y., Matsumoto, T., Fukushima, Y., Mimura, M., Hirohata, M., Matsumoto, N. & Kai, F. (1998). Polyhedron, 17, 1943–1952. CrossRef CAS Google Scholar
Tavacoli, S., Miller, T. A., Paul, R. L., Jeffery, J. C. & Ward, M. D. (2003). Polyhedron, 22, 507–514. CrossRef CAS Google Scholar
Xie, Y. B., Li, J. R. & Bu, X. H. (2005). Polyhedron, 24, 413–418. Web of Science CSD CrossRef CAS Google Scholar
Zhang, S., Tu, C., Wang, X., Yang, Z., Zhang, J., Lin, L., Ding, J. & Guo, Z. (2004). Eur. J. Inorg. Chem. pp. 4028–4035. CrossRef Google Scholar

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