Bis[benzyl N'-(3-phenyl-prop-2-enyl-idene)hydrazinecarbodithio-ato-κN',S]copper(II).

The Cu(II) atom of the title complex, [Cu(C(17)H(15)N(2)S(2))(2)], lies on a twofold rotation axis, and is in a distorted tetra-hedral geometry with the two bidentate N(2)S(2) Schiff bases. In the crystal structure, the mol-ecules are inter-connected into chains along the c axis by weak C-H⋯S inter-molecular inter-actions. The crystal packing is further stabilized by C-H⋯π inter-actions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For the synthesis and structures of S-benzyl­dithio­carbaza­tes, see: Ali & Tarafder (1977 ▶); Shanmuga Sundara Raj et al. (2000 ▶). For related CuII complexes, see: Ali et al. (2008 ▶); Castiñeiras et al. (1998 ▶); Goswami & Eichhorn (2000 ▶). For bioactivities of S-benzyl­dithio­carbazate metal complexes, see: Ali et al. (2002 ▶, 2008 ▶); Tarafder et al. (2001 ▶, 2002 ▶).

Experimental

Crystal data

[Cu(C17H15N2S2)2]

M = 686.45

Orthorhombic,

a = 36.1410 (7) Å

b = 9.9372 (2) Å

c = 8.7598 (2) Å

V = 3146.00 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.99 mm−1

T = 100.0 (1) K

0.57 × 0.29 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.603, T max = 0.906

84850 measured reflections

6922 independent reflections

5675 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.083

S = 1.04

6922 reflections

196 parameters

H-atom parameters constrained

Δρmax = 0.52 e Å−3

Δρmin = −0.43 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808002262/ci2558sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808002262/ci2558Isup2.hkl

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

[Cu(C17H15N2S2)2]	F000 = 1420
Mr = 686.45	Dx = 1.449 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 6922 reflections
a = 36.1410 (7) Å	θ = 2.1–35.0º
b = 9.9372 (2) Å	µ = 0.99 mm−1
c = 8.7598 (2) Å	T = 100.0 (1) K
V = 3146.00 (11) Å3	Plate, green
Z = 4	0.57 × 0.29 × 0.10 mm

Bruker SMART APEXII CCD area-detector diffractometer	6922 independent reflections
Radiation source: fine-focus sealed tube	5675 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.047
Detector resolution: 8.33 pixels mm-1	θmax = 35.0º
T = 100.0(1) K	θmin = 2.1º
ω scans	h = −58→57
Absorption correction: multi-scan(SADABS; Bruker, 2005)	k = −16→16
Tmin = 0.603, Tmax = 0.906	l = −13→14
84850 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.083	w = 1/[σ2(Fo2) + (0.0303P)2 + 2.083P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
6922 reflections	Δρmax = 0.52 e Å−3
196 parameters	Δρmin = −0.43 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temparture data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	0.0000	0.07778 (2)	0.7500	0.01578 (5)
S1	−0.056798 (8)	−0.01045 (3)	0.70614 (4)	0.02194 (6)
S2	−0.126264 (8)	0.09538 (4)	0.81392 (4)	0.02454 (7)
N1	0.02535 (3)	0.20538 (10)	0.59588 (11)	0.01718 (17)
N2	0.06393 (3)	0.20720 (10)	0.59855 (12)	0.01796 (17)
C1	−0.10931 (3)	0.28518 (12)	0.39861 (14)	0.0206 (2)
H1A	−0.1006	0.2148	0.4586	0.025*
C2	−0.14653 (3)	0.29131 (13)	0.36079 (15)	0.0229 (2)
H2A	−0.1626	0.2252	0.3961	0.027*
C3	−0.15998 (3)	0.39565 (14)	0.27034 (15)	0.0239 (2)
H3A	−0.1850	0.3998	0.2462	0.029*
C4	−0.13588 (4)	0.49338 (15)	0.21640 (16)	0.0251 (2)
H4A	−0.1447	0.5625	0.1548	0.030*
C5	−0.09847 (3)	0.48806 (13)	0.25450 (15)	0.0222 (2)
H5A	−0.0825	0.5539	0.2181	0.027*
C6	−0.08476 (3)	0.38468 (12)	0.34685 (13)	0.01828 (19)
C7	−0.04535 (3)	0.38225 (12)	0.38369 (14)	0.0192 (2)
H7A	−0.0305	0.4468	0.3374	0.023*
C8	−0.02862 (3)	0.29470 (12)	0.47880 (14)	0.0194 (2)
H8A	−0.0433	0.2341	0.5325	0.023*
C9	0.01065 (3)	0.29035 (12)	0.50134 (13)	0.01849 (19)
H9A	0.0258	0.3493	0.4474	0.022*
C10	−0.07825 (3)	0.11156 (12)	0.81865 (13)	0.01794 (19)
C11	−0.14240 (3)	0.20513 (14)	0.96662 (15)	0.0230 (2)
H11A	−0.1295	0.1852	1.0611	0.028*
H11B	−0.1381	0.2987	0.9405	0.028*
C12	−0.18327 (3)	0.17791 (13)	0.98351 (14)	0.0210 (2)
C13	−0.19556 (4)	0.07096 (16)	1.07276 (17)	0.0295 (3)
H13A	−0.1784	0.0166	1.1223	0.035*
C14	−0.23304 (4)	0.04438 (17)	1.08878 (18)	0.0326 (3)
H14A	−0.2409	−0.0266	1.1499	0.039*
C15	−0.25879 (3)	0.12346 (16)	1.01385 (16)	0.0282 (3)
H15A	−0.2839	0.1059	1.0246	0.034*
C16	−0.24696 (4)	0.22864 (16)	0.92307 (19)	0.0318 (3)
H16A	−0.2642	0.2813	0.8717	0.038*
C17	−0.20935 (4)	0.25621 (15)	0.90804 (18)	0.0284 (3)
H17A	−0.2016	0.3275	0.8471	0.034*

	U11	U22	U33	U12	U13	U23
Cu1	0.01427 (8)	0.01721 (9)	0.01586 (8)	0.000	0.00375 (6)	0.000
S1	0.02087 (12)	0.02213 (13)	0.02284 (13)	−0.00456 (10)	0.00520 (10)	−0.00534 (10)
S2	0.01540 (12)	0.03281 (16)	0.02541 (15)	−0.00349 (11)	−0.00031 (10)	−0.00859 (12)
N1	0.0146 (4)	0.0197 (4)	0.0172 (4)	0.0005 (3)	0.0006 (3)	−0.0007 (3)
N2	0.0132 (4)	0.0216 (4)	0.0190 (4)	−0.0009 (3)	0.0002 (3)	0.0003 (3)
C1	0.0179 (5)	0.0216 (5)	0.0222 (5)	0.0011 (4)	0.0005 (4)	0.0008 (4)
C2	0.0181 (5)	0.0250 (5)	0.0254 (6)	−0.0006 (4)	0.0010 (4)	−0.0017 (5)
C3	0.0180 (5)	0.0302 (6)	0.0236 (6)	0.0046 (4)	−0.0021 (4)	−0.0034 (5)
C4	0.0225 (5)	0.0287 (6)	0.0242 (6)	0.0055 (5)	−0.0033 (4)	0.0034 (5)
C5	0.0213 (5)	0.0231 (5)	0.0222 (5)	0.0013 (4)	−0.0004 (4)	0.0031 (4)
C6	0.0165 (4)	0.0205 (5)	0.0178 (5)	0.0017 (4)	−0.0001 (4)	−0.0009 (4)
C7	0.0169 (4)	0.0209 (5)	0.0199 (5)	−0.0002 (4)	0.0008 (4)	0.0006 (4)
C8	0.0153 (4)	0.0224 (5)	0.0203 (5)	−0.0004 (4)	0.0006 (4)	0.0016 (4)
C9	0.0161 (4)	0.0213 (5)	0.0181 (5)	−0.0003 (4)	0.0005 (4)	0.0009 (4)
C10	0.0159 (4)	0.0213 (5)	0.0167 (5)	−0.0014 (4)	0.0009 (3)	0.0001 (4)
C11	0.0153 (5)	0.0284 (6)	0.0254 (6)	−0.0008 (4)	−0.0003 (4)	−0.0058 (5)
C12	0.0149 (4)	0.0257 (5)	0.0223 (5)	0.0001 (4)	−0.0014 (4)	−0.0032 (4)
C13	0.0198 (5)	0.0381 (7)	0.0308 (7)	0.0006 (5)	−0.0043 (5)	0.0095 (6)
C14	0.0224 (6)	0.0428 (8)	0.0326 (7)	−0.0063 (5)	−0.0008 (5)	0.0105 (6)
C15	0.0159 (5)	0.0398 (7)	0.0290 (6)	−0.0030 (5)	0.0005 (4)	−0.0015 (6)
C16	0.0171 (5)	0.0363 (7)	0.0419 (8)	0.0034 (5)	−0.0039 (5)	0.0057 (6)
C17	0.0190 (5)	0.0294 (6)	0.0370 (7)	0.0005 (5)	−0.0012 (5)	0.0070 (5)

Cu1—N1i	2.0663 (10)	C6—C7	1.4606 (16)
Cu1—N1	2.0663 (10)	C7—C8	1.3478 (17)
Cu1—S1i	2.2648 (3)	C7—H7A	0.93
Cu1—S1	2.2649 (3)	C8—C9	1.4335 (16)
S1—C10	1.7442 (12)	C8—H8A	0.93
S2—C10	1.7432 (11)	C9—H9A	0.93
S2—C11	1.8217 (13)	C10—N2i	1.3027 (15)
N1—C9	1.2965 (15)	C11—C12	1.5088 (16)
N1—N2	1.3949 (13)	C11—H11A	0.97
N2—C10i	1.3027 (15)	C11—H11B	0.97
C1—C2	1.3866 (16)	C12—C17	1.3897 (18)
C1—C6	1.4037 (17)	C12—C13	1.3922 (19)
C1—H1A	0.93	C13—C14	1.3871 (19)
C2—C3	1.3926 (19)	C13—H13A	0.93
C2—H2A	0.93	C14—C15	1.384 (2)
C3—C4	1.388 (2)	C14—H14A	0.93
C3—H3A	0.93	C15—C16	1.381 (2)
C4—C5	1.3937 (17)	C15—H15A	0.93
C4—H4A	0.93	C16—C17	1.3927 (19)
C5—C6	1.3983 (17)	C16—H16A	0.93
C5—H5A	0.93	C17—H17A	0.93
N1i—Cu1—N1	104.29 (5)	C7—C8—C9	123.27 (11)
N1i—Cu1—S1i	121.90 (3)	C7—C8—H8A	118.4
N1—Cu1—S1i	86.94 (3)	C9—C8—H8A	118.4
N1i—Cu1—S1	86.94 (3)	N1—C9—C8	120.88 (11)
N1—Cu1—S1	121.90 (3)	N1—C9—H9A	119.6
S1i—Cu1—S1	134.452 (19)	C8—C9—H9A	119.6
C10—S1—Cu1	92.17 (4)	N2i—C10—S2	118.41 (9)
C10—S2—C11	104.25 (6)	N2i—C10—S1	130.18 (9)
C9—N1—N2	114.32 (10)	S2—C10—S1	111.41 (6)
C9—N1—Cu1	129.45 (8)	C12—C11—S2	106.15 (8)
N2—N1—Cu1	116.12 (7)	C12—C11—H11A	110.5
C10i—N2—N1	113.39 (10)	S2—C11—H11A	110.5
C2—C1—C6	120.33 (11)	C12—C11—H11B	110.5
C2—C1—H1A	119.8	S2—C11—H11B	110.5
C6—C1—H1A	119.8	H11A—C11—H11B	108.7
C1—C2—C3	120.49 (12)	C17—C12—C13	118.55 (11)
C1—C2—H2A	119.8	C17—C12—C11	121.14 (12)
C3—C2—H2A	119.8	C13—C12—C11	120.29 (11)
C4—C3—C2	119.71 (11)	C14—C13—C12	120.92 (13)
C4—C3—H3A	120.1	C14—C13—H13A	119.5
C2—C3—H3A	120.1	C12—C13—H13A	119.5
C3—C4—C5	120.07 (12)	C15—C14—C13	120.04 (14)
C3—C4—H4A	120.0	C15—C14—H14A	120.0
C5—C4—H4A	120.0	C13—C14—H14A	120.0
C4—C5—C6	120.68 (12)	C16—C15—C14	119.66 (12)
C4—C5—H5A	119.7	C16—C15—H15A	120.2
C6—C5—H5A	119.7	C14—C15—H15A	120.2
C5—C6—C1	118.71 (11)	C15—C16—C17	120.35 (13)
C5—C6—C7	119.04 (11)	C15—C16—H16A	119.8
C1—C6—C7	122.23 (11)	C17—C16—H16A	119.8
C8—C7—C6	125.77 (11)	C12—C17—C16	120.46 (13)
C8—C7—H7A	117.1	C12—C17—H17A	119.8
C6—C7—H7A	117.1	C16—C17—H17A	119.8
N1i—Cu1—S1—C10	6.84 (5)	C1—C6—C7—C8	−5.87 (19)
N1—Cu1—S1—C10	−98.11 (5)	C6—C7—C8—C9	174.88 (11)
S1i—Cu1—S1—C10	140.38 (4)	N2—N1—C9—C8	176.16 (10)
N1i—Cu1—N1—C9	−64.62 (10)	Cu1—N1—C9—C8	−7.90 (17)
S1i—Cu1—N1—C9	173.21 (11)	C7—C8—C9—N1	179.00 (12)
S1—Cu1—N1—C9	30.76 (12)	C11—S2—C10—N2i	−11.46 (12)
N1i—Cu1—N1—N2	111.27 (8)	C11—S2—C10—S1	168.25 (7)
S1i—Cu1—N1—N2	−10.91 (7)	Cu1—S1—C10—N2i	−4.35 (12)
S1—Cu1—N1—N2	−153.36 (7)	Cu1—S1—C10—S2	175.98 (6)
C9—N1—N2—C10i	−172.92 (11)	C10—S2—C11—C12	−171.27 (9)
Cu1—N1—N2—C10i	10.56 (12)	S2—C11—C12—C17	−94.14 (13)
C6—C1—C2—C3	0.38 (19)	S2—C11—C12—C13	84.28 (14)
C1—C2—C3—C4	0.7 (2)	C17—C12—C13—C14	−1.3 (2)
C2—C3—C4—C5	−0.9 (2)	C11—C12—C13—C14	−179.71 (14)
C3—C4—C5—C6	0.1 (2)	C12—C13—C14—C15	0.9 (2)
C4—C5—C6—C1	0.94 (19)	C13—C14—C15—C16	0.1 (2)
C4—C5—C6—C7	179.73 (12)	C14—C15—C16—C17	−0.7 (2)
C2—C1—C6—C5	−1.18 (18)	C13—C12—C17—C16	0.6 (2)
C2—C1—C6—C7	−179.93 (11)	C11—C12—C17—C16	179.09 (13)
C5—C6—C7—C8	175.39 (12)	C15—C16—C17—C12	0.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···S2ii	0.93	2.76	3.6698 (15)	167
C11—H11A···Cg1iii	0.97	2.98	3.5806 (14)	121

Cu1—N1	2.0663 (10)
Cu1—S1	2.2649 (3)

N1i—Cu1—N1	104.29 (5)
N1—Cu1—S1i	86.94 (3)
N1—Cu1—S1	121.90 (3)
S1i—Cu1—S1	134.452 (19)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯S2ii	0.93	2.76	3.6698 (15)	167
C11—H11A⋯Cg1iii	0.97	2.98	3.5806 (14)	121

Symmetry codes: (ii) ; (iii) .