Bis[benzyl N′-(3-phenyl­prop-2-enyl­idene)hydrazinecarbodithio­ato-κ2N′,S]copper(II)

Tarafder, M.T.H.; Islam, M.T.; Islam, M.A.A.A.A.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536808002262

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 2| February 2008| Pages m416-m417

doi:10.1107/S1600536808002262

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Bis[benzyl N′-(3-phenylprop-2-enylidene)hydrazinecarbodithioato-κ²N′,S]copper(II)

M. T. H. Tarafder,^a ^* M. Toihidul Islam,^a M. A. A. A. A. Islam,^b Suchada Chantrapromma ^c ‡ and Hoong-Kun Fun ^d §

^aDepartment of Chemistry, Rajshahi University, Rajshahi 6205, Bangladesh, ^bDepartment of Chemistry, Rajshahi University of Engineering and Technology, Rajshahi 6205, Bangladesh, ^cDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^dX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: ttofazzal@yahoo.com

(Received 18 January 2008; accepted 22 January 2008; online 25 January 2008)

The Cu^II atom of the title complex, [Cu(C₁₇H₁₅N₂S₂)₂], lies on a twofold rotation axis, and is in a distorted tetrahedral geometry with the two bidentate N₂S₂ Schiff bases. In the crystal structure, the molecules are interconnected into chains along the c axis by weak C—H⋯S intermolecular interactions. The crystal packing is further stabilized by C—H⋯π interactions.

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 Cu^II 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_r = 686.45
Orthorhombic, P b c n
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.083
S = 1.04
6922 reflections
196 parameters
H-atom parameters constrained
Δρ_max = 0.52 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

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) $[-x, y, -z+{\script{3\over 2}}]$ .

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) $[x, -y, z+{\script{1\over 2}}]$ ; (iii) x, y, z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Synthesis (Ali & Tarafder, 1977) and crystal structure (Shanmuga Sundara Raj et al., 2000) of S-benzyldithiocarbazate (SBDTC) have been reported. We have been greatly involved in the chemistry of Schiff bases derived from SBDTC, and also on their metal complexes because of their interesting physico-chemical properties and potentially useful biological activities (Ali et al., 2002, 2008; Tarafder et al., 2001, 2002). In continuation of our interests, we report herein the syntheses of the cinnamaldehyde Schiff base of SBDTC and its copper complex, along with the x-ray structural analysis of the four-coordinated Cu^II complex.

The Cu^II atom of the title complex, lies on a twofold rotation axis and the asymmetric unit therefore contains one-half of a molecule (Fig. 1). Based on other thiosemicarbazones (Ali et al., 2002; Tarafder et al., 2001, 2002), the coordination mode of the Cu^II complex is as expected, i.e bis-chelated through the two azomethine nitrogen atoms and the two thiolate sulfur atoms. The Cu^II center is in a distorted tetrahedral geometry with the N₂S₂ donor atoms of the two Schiff base ligands (Fig. 1). Both nitrogen atoms (N1 and N1A) and sulfur atoms (S1 and S1A) from the two ligands are coordinated at opposite positions. The N—Cu—N and S—Cu—S bond angles are 104.29 (5)° and 134.452 (14)°, respectively, and reflective of the elongation of the Cu—S bond length [ca 0.19 Å] over the Cu—N bond length. The Cu1—N1 and Cu1—S1 distances of 2.0663 (10) Å and 2.2648 (3) Å, respectively, are in the same range as those in other four coordination Cu^II complexes of the related Schiff base ligands (Ali et al., 2008; Castiñeiras et al., 1998; Goswami & Eichhorn, 2000). The Cu^II-bidentate rings are slightly non-planar. The Cu1—S1—N1A—N2A—C10 ring has a maximum deviation of 0.085 (1) Å for the N1A atom. The mean plane of the propenyl moiety (C7/C8/C9) makes a dihedral angle of 12.15 (9)° with mean plane of the attached C1–C6 benzene ring. The dihedral angle between the C1–C6 and C12–C17 phenyl rings of the two ligands is 8.73 (7)°. Bond lengths and angles observed in the Schiff base ligand are of normal values (Allen et al., 1987).

In the crystal packing (Fig. 2), the molecules are interconnected by weak C—H···S intermolecular interactions (Table 1) into chains along the c axis. The crystal structure is further stabilized by C—H···π interactions (Table 2) involving the C1—C6 benzene ring (centroid Cg1).

Related literature top

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 Cu^II 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 top

The Schiff base ligand was prepared by adding cinamaldehyde (1.32 g, 10 mmol) to a hot solution of S-benzyldithiocarbazate (SBDTC) (1.98 g, 10 mmol) in absolute ethanol (40 ml), as reported previously (Ali & Tarafder, 1977). The mixture was refluxed for 10 min. The yellow precipitate which formed was isolated and washed with hot ethanol. The yellow solid product was recrystallized from absolute ethanol (yield: 1.52 g, 46%). The copper complex was synthesized by adding the copper nitrate trihydrate (0.31 g, 0.5 mmol) in ethanol (10 ml) to a hot solution of the above Schiff base ligand (0.31 g, 1 mmol) in ethanol (80 ml) and the reaction mixture was refluxed for 5 min when a brownish precipitate was formed. The product was separated and washed with hot ethanol (yield: 0.32 g, 74%). Green single crystals of the title complex were recrystallized from a chloroform-absolute ethanol (10:3 V/V) solution after 20 d at room temperature.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids. Atoms labelled with the suffix A are generated by the symmetry operation (-x, y, 3/2 - z).
	Fig. 2. Part of the crystal packing of the title compound, viewed along the b axis. Intermolecular C—H···S weak interactions are shown as dashed lines.

Bis[benzyl N'-(3-phenylprop-2-enylidene)hydrazinecarbodithioato- κ²N',S]copper(II) top

Crystal data top

[Cu(C₁₇H₁₅N₂S₂)₂]	F(000) = 1420
M_r = 686.45	D_x = 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 = 2.1–35.0°
b = 9.9372 (2) Å	µ = 0.99 mm⁻¹
c = 8.7598 (2) Å	T = 100 K
V = 3146.00 (11) Å³	Plate, green
Z = 4	0.57 × 0.29 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6922 independent reflections
Radiation source: fine-focus sealed tube	5675 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 8.33 pixels mm^-1	θ_max = 35.0°, θ_min = 2.1°
ω scans	h = −58→57
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −16→16
T_min = 0.603, T_max = 0.906	l = −13→14
84850 measured reflections

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0303P)² + 2.083P] where P = (F_o² + 2F_c²)/3
6922 reflections	(Δ/σ)_max = 0.001
196 parameters	Δρ_max = 0.52 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Cu(C₁₇H₁₅N₂S₂)₂]	V = 3146.00 (11) Å³
M_r = 686.45	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 36.1410 (7) Å	µ = 0.99 mm⁻¹
b = 9.9372 (2) Å	T = 100 K
c = 8.7598 (2) Å	0.57 × 0.29 × 0.10 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	6922 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	5675 reflections with I > 2σ(I)
T_min = 0.603, T_max = 0.906	R_int = 0.047
84850 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.04	Δρ_max = 0.52 e Å⁻³
6922 reflections	Δρ_min = −0.43 e Å⁻³
196 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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) x, −y, z+1/2; (iii) x, y, z+1.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₇H₁₅N₂S₂)₂]
M_r	686.45
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	36.1410 (7), 9.9372 (2), 8.7598 (2)
V (Å³)	3146.00 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.57 × 0.29 × 0.10

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.603, 0.906
No. of measured, independent and observed [I > 2σ(I)] reflections	84850, 6922, 5675
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.807

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.083, 1.04
No. of reflections	6922
No. of parameters	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.52, −0.43

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) top

Cu1—N1	2.0663 (10)	Cu1—S1	2.2649 (3)

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

Symmetry code: (i) −x, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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) x, −y, z+1/2; (iii) x, y, z+1.

Footnotes

‡Additional correspondence author, email: suchada.c@psu.ac.th.

§Additional correspondence author, email: hkfun@usm.my.

Acknowledgements

MTHT and MTI thank Rajshahi University for financial support. The authors thank the Malaysian Government and Universiti Sains Malaysia for the Scientific Advancement Grant Allocation (SAGA) grant No. 304/PFIZIK/653003/A118.

References

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