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

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

doi:10.1107/S1600536808005643

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m518-m519

doi:10.1107/S1600536808005643

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

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

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

(Received 25 February 2008; accepted 28 February 2008; online 5 March 2008)

In the title Zn^II complex, [Zn(C₁₇H₁₅N₂S₂)₂], the Zn^II atom lies on a twofold rotation axis. It exists in a tetrahedral geometry, chelated by two deprotonated Schiff base ligands. The dihedral angle between each ligand is 71.48 (8)°. Molecules are connected by weak C—H⋯S intermolecular interactions into chains along the c axis. The crystal structure is further stabilized by C—H⋯π interactions involving the phenyl ring of the 3-phenylprop-2-enylidene unit.

Related literature

For the synthesis and structure of S-benzyldithiocarbazates, see: Ali & Tarafder (1977 ); Shanmuga Sundara Raj et al. (2000 ). For the structures of Zn^II complexes, see: Latheef et al. (2007 ); Tarafder, Chew et al. (2002 ). For the structures of other metal dithiocarbazates, see: Ali et al. (2001 , 2002 , 2008 ); Chew et al. (2004 ); Crouse et al. (2004 ); Tarafder et al. (2001 , 2008 ); Tarafder, Chew et al. (2002); Tarafder, Jin et al. (2002 ). For the bioactivity of metal S-benzyldithiocarbazates, see, for example: Ali et al. (2001, 2002); Tarafder et al. (2001); Tarafder, Jin et al. (2002).

Experimental

Crystal data

[Zn(C₁₇H₁₅N₂S₂)₂]
M_r = 688.23
Orthorhombic, P b c n
a = 36.0897 (4) Å
b = 9.9310 (1) Å
c = 8.7633 (1) Å
V = 3140.83 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.08 mm⁻¹
T = 100.0 (1) K
0.37 × 0.25 × 0.17 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.692, T_max = 0.841
82655 measured reflections
4580 independent reflections
4071 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.091
S = 1.15
4580 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯S2ⁱ	0.93	2.76	3.6697 (17)	167
C11—H11B⋯Cg1ⁱⁱ	0.97	2.98	3.5785 (17)	121
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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/S1600536808005643/ng2427sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808005643/ng2427Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of the ligands derived from S-benzyldithiocarbazate (SBDTC) had been of immense interests because of their intriguing coordination chemistry as well as their increasingly important biomedical properties (Ali et al., 2001; 2002; Tarafder et al., 2001; Tarafder, Jin et al., 2002b). Synthesis (Ali & Tarafder, 1977) and structure (Shanmuga Sundara Raj et al., 2000) of SBDTC were reported. We have previously reported the Schiff bases complexes derived from dithiocarbazate derivatives (Ali et al., 2001; 2002; 2008; Chew et al., 2004; Crouse et al., 2004; Tarafder et al., 2001, 2008; Tarafder, Chew et al., 2002; Tarafder, Jin et al., 2002). In continuation of our interests, we report herein the X-ray structure of the zinc(II) complex of Schiff base ligand of SBDTC which is found to be isostructural with the copper(II) analog (Tarafder et al., 2008).

The Zn^II atom of the title complex, lies on a twofold rotation axis and therefore the asymmetric unit contains one-half of a molecule (Fig. 1). The ligands coordinate to the Zn^II through the two azomethine nitrogen and the two thiolate sulfur atoms forming a distorted tetrahedral geometry (Fig. 1). Both the two nitrogen atoms (N1 and N1A) and two sulfur atoms (S1 and S1A) from the two ligands are coordinated at opposite positions. The NS chelation results in the two five membered Zn^II-bidentate rings (Zn1, N1, N2, C8, S1), atom Zn1 having a maximum deviation of 0.0839 (5) Å. The dihedral angle between these Zn^II-bidentate rings is 80.03 (4) °. The smaller angle around Zn^II is 86.96 (3) ° for N1—Zn1—S1. The N—Zn—N and S—Zn—S bond angles are 104.32 (7) ° and 134.49 (2) °, respectively. The Zn1—N1 distance of 2.0662 (12) Å is slightly longer compared to the [Zn(C₁₄H₁₈N₃OS)₂] by Latheef et al., 2007 (Zn—N = 2.026 (3) and 2.040 (3) Å) whereas the Zn1—S1 distance of 2.2636 (4) Å in the title complex is in the same range (Zn—S = 2.2597 (13) and 2.2462 (12) Å (Latheef et al., 2007)). The mean plane of the prop-2-enylidene moiety (C7/C8/C9/N1/N2) makes a dihedral angle of 12.25 (12)° with mean plane of the attached C1–C6 phenyl ring. Atoms N1, N2, C10, S1 and S2 lie on the same plane and this plane makes a dihedral angle of 76.75 (6) ° with the C12–C17 phenyl ring. The dihedral angle between the two phenhyl rings (C1–C6 and C12–C17) is 71.48 (8)°. Bond lengths and angles observed in the Schiff base ligand are of normal values.

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 is further stabilized by C—H···π interactions (Table 1) involving the C1–C6 phenyl ring (centroid Cg₁) of the 3-phenylprop-2-enylidene moiety.

Related literature top

For the synthesis and structure of S-benzyldithiocarbazates, see: Ali & Tarafder (1977); Shanmuga Sundara Raj et al. (2000). For the structures of Zn^II complexes, see: Latheef et al. (2007); Tarafder et al. (2002a). For the structures of other metal dithiocarbazates, see: Ali et al. (2001, 2002, 2008); Chew et al. (2004); Crouse et al. (2004); Tarafder et al. (2001, 2008); Tarafder, Chew et al. (2002); Tarafder, Jin et al. (2002). For the bioactivity of metal S-benzyldithiocarbazates, see: for example, Ali et al. (2001, 2002); Tarafder et al. (2001); Tarafder, Jin et al. (2002).

Experimental top

The Schiff base ligand was prepared following the literature procedure (Tarafder et al., 2008) 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). The mixture was refluxed for 10 min. The yellow precipitate, which formed, was isolated and washed with hot ethanol. The yellow solid was recrystallized from absolute ethanol (Yield: 1.52 g, 46%). The zinc complex was synthesized by adding the solution of the Schiff base ligand (0.31 g, 1 mmol) in absolute ethanol (70 ml) to a solution of zinc nitrate hexahydrate (0.15 g, 0.5 mmol) in absolute ethanol (5 ml) and stirred under boiling condition for 10 min. A resultant yellow precipitate was separated and washed with hot ethanol (Yield: 0.29 g, 63%). Yellow single crystals of the title complex were crystallized from a mixture solution of chloroform/absolute ethanol (70:5 v/v) after 40 days at room temperature and further recrystallized from chloroform (40 ml) by slow evaporation at 296 K after 10 days, M.p 457–458 K.

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 asymmetric unit of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering. Atoms labelled with suffix A are generated by the symmetry operation (-x, y, 1/2 - z).
	Fig. 2. 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]zinc(II) top

Crystal data top

[Zn(C₁₇H₁₅N₂S₂)₂]	D_x = 1.455 Mg m⁻³
M_r = 688.23	Melting point = 457–458 K
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4580 reflections
a = 36.0897 (4) Å	θ = 1.1–30.0°
b = 9.9310 (1) Å	µ = 1.08 mm⁻¹
c = 8.7633 (1) Å	T = 100 K
V = 3140.83 (6) Å³	Block, yellow
Z = 4	0.37 × 0.25 × 0.17 mm
F(000) = 1424

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4580 independent reflections
Radiation source: fine-focus sealed tube	4071 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 8.33 pixels mm^-1	θ_max = 30.0°, θ_min = 1.1°
ω scans	h = −50→50
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
T_min = 0.692, T_max = 0.841	l = −12→12
82655 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.091	H-atom parameters constrained
S = 1.15	w = 1/[σ²(F_o²) + (0.0478P)² + 1.4067P] where P = (F_o² + 2F_c²)/3
4580 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

[Zn(C₁₇H₁₅N₂S₂)₂]	V = 3140.83 (6) Å³
M_r = 688.23	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 36.0897 (4) Å	µ = 1.08 mm⁻¹
b = 9.9310 (1) Å	T = 100 K
c = 8.7633 (1) Å	0.37 × 0.25 × 0.17 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	4580 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4071 reflections with I > 2σ(I)
T_min = 0.692, T_max = 0.841	R_int = 0.042
82655 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.091	H-atom parameters constrained
S = 1.15	Δρ_max = 0.49 e Å⁻³
4580 reflections	Δρ_min = −0.32 e Å⁻³
195 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
Zn1	0.0000	0.42216 (2)	0.2500	0.01855 (8)
S1	−0.056843 (10)	0.51031 (4)	0.20596 (5)	0.02295 (9)
S2	−0.126368 (10)	0.40453 (4)	0.31408 (5)	0.02541 (10)
N1	−0.02538 (3)	0.29452 (12)	0.40410 (14)	0.0177 (2)
N2	−0.06402 (3)	0.29289 (12)	0.40147 (14)	0.0183 (2)
C1	0.10940 (4)	0.21479 (15)	0.60174 (17)	0.0215 (3)
H1A	0.1007	0.2854	0.5420	0.026*
C2	0.14657 (4)	0.20851 (16)	0.63939 (18)	0.0238 (3)
H2B	0.1627	0.2745	0.6040	0.029*
C3	0.16001 (4)	0.10408 (18)	0.72987 (18)	0.0251 (3)
H3A	0.1851	0.0999	0.7541	0.030*
C4	0.13595 (4)	0.00646 (18)	0.78363 (19)	0.0263 (3)
H4A	0.1448	−0.0627	0.8451	0.032*
C5	0.09847 (4)	0.01154 (17)	0.74589 (18)	0.0233 (3)
H5A	0.0824	−0.0543	0.7825	0.028*
C6	0.08479 (4)	0.11508 (15)	0.65326 (16)	0.0191 (3)
C7	0.04530 (4)	0.11779 (15)	0.61642 (17)	0.0197 (3)
H7A	0.0304	0.0534	0.6627	0.024*
C8	0.02865 (4)	0.20541 (15)	0.52127 (17)	0.0203 (3)
H8A	0.0434	0.2660	0.4676	0.024*
C9	−0.01069 (4)	0.20968 (15)	0.49886 (16)	0.0194 (3)
H9A	−0.0258	0.1509	0.5530	0.023*
C10	−0.07830 (4)	0.38814 (15)	0.31855 (16)	0.0188 (3)
C11	−0.14245 (4)	0.29477 (17)	0.46680 (18)	0.0239 (3)
H11A	−0.1382	0.2011	0.4407	0.029*
H11B	−0.1295	0.3146	0.5611	0.029*
C12	−0.18343 (4)	0.32244 (15)	0.48382 (17)	0.0216 (3)
C13	−0.19570 (4)	0.42883 (18)	0.5729 (2)	0.0300 (3)
H13A	−0.1785	0.4831	0.6226	0.036*
C14	−0.23315 (5)	0.4555 (2)	0.5890 (2)	0.0327 (4)
H14A	−0.2410	0.5265	0.6503	0.039*
C15	−0.25893 (4)	0.37653 (18)	0.51415 (19)	0.0281 (3)
H15A	−0.2841	0.3942	0.5249	0.034*
C16	−0.24710 (4)	0.27147 (19)	0.4234 (2)	0.0316 (4)
H16A	−0.2644	0.2187	0.3722	0.038*
C17	−0.20951 (4)	0.24407 (17)	0.4082 (2)	0.0281 (3)
H17A	−0.2018	0.1729	0.3470	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.01629 (12)	0.02017 (13)	0.01920 (13)	0.000	0.00389 (8)	0.000
S1	0.02122 (17)	0.02294 (18)	0.02470 (18)	0.00512 (13)	0.00525 (14)	0.00599 (14)
S2	0.01511 (16)	0.0341 (2)	0.02701 (19)	0.00377 (14)	−0.00046 (13)	0.00913 (15)
N1	0.0135 (5)	0.0205 (5)	0.0191 (5)	0.0002 (4)	0.0008 (4)	−0.0007 (4)
N2	0.0131 (5)	0.0227 (6)	0.0191 (5)	−0.0007 (4)	−0.0003 (4)	0.0002 (5)
C1	0.0198 (6)	0.0222 (7)	0.0226 (7)	0.0018 (5)	−0.0006 (5)	0.0003 (5)
C2	0.0176 (6)	0.0265 (7)	0.0272 (7)	−0.0010 (5)	0.0016 (5)	−0.0024 (6)
C3	0.0168 (6)	0.0325 (8)	0.0260 (7)	0.0047 (6)	−0.0026 (5)	−0.0048 (6)
C4	0.0240 (7)	0.0294 (8)	0.0255 (7)	0.0061 (6)	−0.0039 (6)	0.0025 (6)
C5	0.0214 (7)	0.0241 (7)	0.0243 (7)	0.0016 (6)	−0.0001 (5)	0.0029 (6)
C6	0.0166 (6)	0.0224 (6)	0.0184 (6)	0.0019 (5)	−0.0006 (5)	−0.0011 (5)
C7	0.0163 (6)	0.0228 (7)	0.0199 (6)	−0.0003 (5)	0.0008 (5)	−0.0003 (5)
C8	0.0155 (6)	0.0235 (7)	0.0219 (6)	−0.0004 (5)	0.0011 (5)	0.0008 (5)
C9	0.0164 (6)	0.0226 (7)	0.0192 (6)	−0.0007 (5)	0.0009 (5)	0.0008 (5)
C10	0.0156 (6)	0.0227 (7)	0.0182 (6)	0.0008 (5)	0.0010 (5)	−0.0008 (5)
C11	0.0151 (6)	0.0301 (8)	0.0266 (7)	0.0006 (5)	−0.0003 (5)	0.0060 (6)
C12	0.0148 (6)	0.0268 (7)	0.0230 (7)	0.0001 (5)	−0.0011 (5)	0.0044 (6)
C13	0.0212 (7)	0.0377 (9)	0.0311 (8)	−0.0008 (6)	−0.0057 (6)	−0.0092 (7)
C14	0.0235 (8)	0.0425 (10)	0.0322 (8)	0.0068 (7)	−0.0010 (6)	−0.0106 (8)
C15	0.0153 (6)	0.0392 (9)	0.0297 (8)	0.0025 (6)	0.0009 (6)	0.0018 (7)
C16	0.0172 (7)	0.0347 (9)	0.0428 (10)	−0.0042 (6)	−0.0036 (6)	−0.0053 (7)
C17	0.0189 (7)	0.0273 (8)	0.0380 (9)	−0.0004 (6)	−0.0015 (6)	−0.0070 (7)

Geometric parameters (Å, º) top

Zn1—N1	2.0662 (12)	C6—C7	1.4616 (19)
Zn1—N1ⁱ	2.0662 (12)	C7—C8	1.347 (2)
Zn1—S1ⁱ	2.2634 (4)	C7—H7A	0.9300
Zn1—S1	2.2636 (4)	C8—C9	1.4337 (19)
S1—C10	1.7450 (15)	C8—H8A	0.9300
S2—C10	1.7428 (14)	C9—H9A	0.9300
S2—C11	1.8210 (16)	C11—C12	1.5118 (19)
N1—C9	1.2964 (18)	C11—H11A	0.9700
N1—N2	1.3948 (15)	C11—H11B	0.9700
N2—C10	1.2994 (19)	C12—C13	1.386 (2)
C1—C2	1.383 (2)	C12—C17	1.390 (2)
C1—C6	1.405 (2)	C13—C14	1.384 (2)
C1—H1A	0.9300	C13—H13A	0.9300
C2—C3	1.393 (2)	C14—C15	1.382 (2)
C2—H2B	0.9300	C14—H14A	0.9300
C3—C4	1.384 (2)	C15—C16	1.379 (2)
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.393 (2)	C16—C17	1.390 (2)
C4—H4A	0.9300	C16—H16A	0.9300
C5—C6	1.400 (2)	C17—H17A	0.9300
C5—H5A	0.9300

N1—Zn1—N1ⁱ	104.32 (7)	C7—C8—C9	123.08 (13)
N1—Zn1—S1ⁱ	121.84 (3)	C7—C8—H8A	118.5
N1ⁱ—Zn1—S1ⁱ	86.96 (3)	C9—C8—H8A	118.5
N1—Zn1—S1	86.96 (3)	N1—C9—C8	120.80 (13)
N1ⁱ—Zn1—S1	121.84 (3)	N1—C9—H9A	119.6
S1ⁱ—Zn1—S1	134.50 (2)	C8—C9—H9A	119.6
C10—S1—Zn1	92.11 (5)	N2—C10—S2	118.39 (11)
C10—S2—C11	104.17 (7)	N2—C10—S1	130.26 (11)
C9—N1—N2	114.33 (12)	S2—C10—S1	111.35 (8)
C9—N1—Zn1	129.50 (10)	C12—C11—S2	105.99 (10)
N2—N1—Zn1	116.07 (9)	C12—C11—H11A	110.5
C10—N2—N1	113.42 (12)	S2—C11—H11A	110.5
C2—C1—C6	120.33 (14)	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	120.48 (14)	C13—C12—C17	118.62 (14)
C1—C2—H2B	119.8	C13—C12—C11	120.44 (14)
C3—C2—H2B	119.8	C17—C12—C11	120.92 (14)
C4—C3—C2	119.80 (14)	C14—C13—C12	121.01 (15)
C4—C3—H3A	120.1	C14—C13—H13A	119.5
C2—C3—H3A	120.1	C12—C13—H13A	119.5
C3—C4—C5	120.19 (15)	C15—C14—C13	120.01 (16)
C3—C4—H4A	119.9	C15—C14—H14A	120.0
C5—C4—H4A	119.9	C13—C14—H14A	120.0
C4—C5—C6	120.44 (15)	C16—C15—C14	119.63 (15)
C4—C5—H5A	119.8	C16—C15—H15A	120.2
C6—C5—H5A	119.8	C14—C15—H15A	120.2
C5—C6—C1	118.75 (13)	C15—C16—C17	120.35 (15)
C5—C6—C7	119.05 (13)	C15—C16—H16A	119.8
C1—C6—C7	122.18 (13)	C17—C16—H16A	119.8
C8—C7—C6	125.72 (14)	C12—C17—C16	120.37 (15)
C8—C7—H7A	117.1	C12—C17—H17A	119.8
C6—C7—H7A	117.1	C16—C17—H17A	119.8

N1—Zn1—S1—C10	−6.84 (6)	C6—C7—C8—C9	−174.96 (14)
N1ⁱ—Zn1—S1—C10	98.14 (6)	N2—N1—C9—C8	−176.13 (12)
S1ⁱ—Zn1—S1—C10	−140.35 (5)	Zn1—N1—C9—C8	7.7 (2)
N1ⁱ—Zn1—N1—C9	64.77 (12)	C7—C8—C9—N1	−178.89 (14)
S1ⁱ—Zn1—N1—C9	−30.62 (14)	N1—N2—C10—S2	−176.19 (9)
S1—Zn1—N1—C9	−173.11 (13)	N1—N2—C10—S1	3.1 (2)
N1ⁱ—Zn1—N1—N2	−111.33 (10)	C11—S2—C10—N2	11.23 (14)
S1ⁱ—Zn1—N1—N2	153.28 (8)	C11—S2—C10—S1	−168.22 (8)
S1—Zn1—N1—N2	10.79 (9)	Zn1—S1—C10—N2	4.50 (14)
C9—N1—N2—C10	172.96 (13)	Zn1—S1—C10—S2	−176.13 (7)
Zn1—N1—N2—C10	−10.34 (15)	C10—S2—C11—C12	171.23 (11)
C6—C1—C2—C3	−0.6 (2)	S2—C11—C12—C13	−84.45 (16)
C1—C2—C3—C4	−0.6 (2)	S2—C11—C12—C17	94.11 (16)
C2—C3—C4—C5	0.8 (2)	C17—C12—C13—C14	1.2 (3)
C3—C4—C5—C6	0.1 (2)	C11—C12—C13—C14	179.80 (16)
C4—C5—C6—C1	−1.2 (2)	C12—C13—C14—C15	−0.8 (3)
C4—C5—C6—C7	−179.72 (14)	C13—C14—C15—C16	−0.1 (3)
C2—C1—C6—C5	1.4 (2)	C14—C15—C16—C17	0.6 (3)
C2—C1—C6—C7	179.91 (14)	C13—C12—C17—C16	−0.7 (3)
C5—C6—C7—C8	−175.41 (15)	C11—C12—C17—C16	−179.28 (16)
C1—C6—C7—C8	6.1 (2)	C15—C16—C17—C12	−0.2 (3)

Symmetry code: (i) −x, y, −z+1/2.

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	3.6697 (17)	167
C11—H11B···Cg1ⁱⁱⁱ	0.97	2.98	3.5785 (17)	121

Symmetry codes: (ii) x, −y+1, z+1/2; (iii) x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	[Zn(C₁₇H₁₅N₂S₂)₂]
M_r	688.23
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	100
a, b, c (Å)	36.0897 (4), 9.9310 (1), 8.7633 (1)
V (Å³)	3140.83 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.08
Crystal size (mm)	0.37 × 0.25 × 0.17

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.692, 0.841
No. of measured, independent and observed [I > 2σ(I)] reflections	82655, 4580, 4071
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.703

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.091, 1.15
No. of reflections	4580
No. of parameters	195
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.32

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···S2ⁱ	0.93	2.7569	3.6697 (17)	167
C11—H11B···Cg1ⁱⁱ	0.97	2.9763	3.5785 (17)	121

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x+1/2, −y+1/2, −z+1.

Footnotes

‡Additional correspondence author, e-mail: hkfun@usm.my.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th.

Acknowledgements

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

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