Bis[benzyl 3-(3-phenyl­prop-2-enyl­idene)dithio­carbazato-κ2N3,S]cadmium

Reza, M.S.; Islam, M.A.A.A.A.; Tarafder, M.T.H.; Sheikh, M.C.; Zangrando, E.

doi:10.1107/S1600536812028127

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 7| July 2012| Pages m976-m977

https://doi.org/10.1107/S1600536812028127

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Bis[benzyl 3-(3-phenylprop-2-enylidene)dithiocarbazato-κ²N³,S]cadmium

M. S. Reza,^a M. A. A. A. A. Islam,^a M. T. H. Tarafder,^b ^* M. C. Sheikh ^c and E. Zangrando ^d

^aDepartment of Chemistry, Rajshahi University of Engineering and Technology, Rajshahi 6204, Bangladesh, ^bDepartment of Chemistry, Rajshahi University, Rajshahi 6205, Bangladesh, ^cDepartment of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan, and ^dDepartment of Chemical and Pharmaceutical Science, Via L. Giorgieri 1, 34127 Trieste, Italy
^*Correspondence e-mail: ttofazzal@yahoo.com

(Received 19 June 2012; accepted 21 June 2012; online 30 June 2012)

In the title complex, [Cd(C₁₇H₁₅N₂S₂)₂], the Cd^II ion is located on a twofold rotation axis and exhibits a coordination number of four within a very distorted coordination environment that is best described as bisphenoidal. The two deprotonated Schiff base ligands chelate the Cd^II ion through the azomethine N and the thiolate S atom. The dihedral angle between the two chelating ligands is 84.01 (9)°. Weak intermolecular C—H⋯S interactions lead to the formation of chains along the c axis.

Related literature

For the structure of uncoordinated Schiff bases, see: Tarafder, Crouse et al. (2008 ); Tarafder, Islam et al. (2008 ). For the isotypic Zn and Hg analogues, see: Fun et al. (2008 ); Islam et al. (2012 ). For the coordination behaviour of metal ions (Co, Ni, Cu, Zn, Cd and Hg) with the cinnamaldehyde Schiff base of S-methyldithiocarbazate, see: Liu et al. (2009 ); Abram et al. (2006 ). For the bioactivity of transition metal complexes of similar Schiff base ligands, see: Chew et al. (2004 ); How et al. (2008 ); Maia et al. (2010 ).

Experimental

Crystal data

[Cd(C₁₇H₁₅N₂S₂)₂]
M_r = 735.26
Orthorhombic, P b c n
a = 36.2497 (7) Å
b = 9.9940 (2) Å
c = 8.9392 (2) Å
V = 3238.49 (12) Å³
Z = 4
Cu Kα radiation
μ = 8.05 mm⁻¹
T = 173 K
0.3 × 0.3 × 0.1 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ) T_min = 0.325, T_max = 0.448
10761 measured reflections
2964 independent reflections
2439 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.115
S = 1.02
2964 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 1.36 e Å⁻³
Δρ_min = −0.52 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cd—N1	2.306 (2)
Cd—S1	2.4285 (9)

N1ⁱ—Cd—N1	103.00 (12)
N1ⁱ—Cd—S1	119.99 (6)
N1—Cd—S1	80.27 (6)
S1—Cd—S1ⁱ	149.19 (5)
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯S2ⁱⁱ	0.95	2.75	3.690 (4)	170
Symmetry code: (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1995); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536812028127/wm2651sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812028127/wm2651Isup2.hkl

checkCIF report

Comment top

In continuation of our interest in exploring the chemistry of Schiff bases derived from S-benzyldithiocarbazate (Tarafder, Crouse et al., 2008; Tarafder, Islam et al., 2008) and of their metal complexes, due to their intriguing coordination behaviour, physico-chemical properties, and potential biological activities, we have completed the syntheses of group 12 metal complexes with the same Schiff base, viz. bis[benzyl N'-(3-phenylprop-2-enylidene)dithiocarbazate]. For the coordination behaviour of metal ions (Co, Ni, Cu, Zn, Cd, and Hg) with the cinnamaldehyde Schiff base of S-methyldithiocarbazate, see: Liu et al. (2009); Abram et al., (2006). For the bioactivity of transition metal complexes of similar Schiff base ligands, see: Chew et al. (2004); How et al. (2008); Maia et al. (2010).

In the present complex the Cd^II ion lies on a twofold rotation axis and therefore the asymmetric unit contains one-half of the molecule (Fig. 1). The fourfold coordination is best described as bisphenoidal, with the Cd^II ion being chelated by two benzyl N'-(3-phenylprop-2-enylidene)dithiocarbazate ligands through the azomethine nitrogen and the thiolate sulfur donors. The two chelating five-membered rings form a dihedral angle of 84.01 (9)°. Since the structure is isotypic with those of Zn (Fun et al., 2008) and Hg (Islam et al., 2012), it is worthwhile to compare the geometries around the metal ions. The M—N bond lengths in the series follow the trend Zn < Cd < Hg (2.0662 (12), 2.306 (2), 2.489 (3) Å) in agreement with the respective ionic radii. On the other hand, among the M—S bond lengths, the Cd—S one is the longest, with values of 2.2636 (4), 2.4285 (9), 2.3668 (11) Å along this series. Moreover, the bite angle N1—Cd—S1 of 80.27 (6)° is in between the values for the Zn (86.96 (3)°) and Hg (77.93 (6)°) complexes.

The crystal packing is consolidated by weak C13–H13···S2 interactions , giving rise to a chain motif extending along the c axis.

Related literature top

For the structure of uncoordinated Schiff bases, see: Tarafder, Crouse et al. (2008); Tarafder, Islam et al. (2008). For the isotypic Zn and Hg analogues, see: Fun et al. (2008); Islam et al. (2012). For the coordination behaviour of metal ions (Co, Ni, Cu, Zn, Cd and Hg) with the cinnamaldehyde Schiff base of S-methyldithiocarbazate, see: Liu et al. (2009); Abram et al. (2006). For the bioactivity of transition metal complexes of similar Schiff base ligands, see: Chew et al. (2004); How et al. (2008); Maia et al. (2010).

Experimental top

The Schiff base, benzyl N'-(3-phenylprop-2-enylidene)hydrazinecarbodithioate was prepared as prevoiusly reported (Tarafder, Islam et al., 2008). Cadmium(II) acetate dihydrate (0.066 g, 0.25 mmol) dissolved in absolute ethanol (20 ml) was added to a hot absolute ethanol solution (50 ml) of the Schiff base (0.163 g, 0.5 mmol) under refluxing condition, which was continued for 2 h. The yellow precipitate which formed was filtered off, washed with hot ethanol and dried in vacuo over anhydrous CaCl₂. Yield: 0.199 g (87%). 54 mg of the compound was dissolved in chloroform (10 ml) at room temperature and mixed with toluene (5 ml). The resultant solution was allowed to stand at ambient temperature. Yellow square-shaped flat single crystals developed after 7 days. (m.p.= 438 K).

Structure description top

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1995); cell refinement: RAPID-AUTO (Rigaku, 1995); data reduction: RAPID-AUTO (Rigaku, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. An ORTEP drawing (ellipsoids at the 50% probability level) of the title compound with the atom labelling scheme. [Symmetry code: (i) -x + 1, y, -z + 3/2.]

Bis[benzyl 3-(3-phenylprop-2-enylidene)dithiocarbazato- κ²N³,S]cadmium top

Crystal data top

[Cd(C₁₇H₁₅N₂S₂)₂]	F(000) = 1496
M_r = 735.26	D_x = 1.508 Mg m⁻³
Orthorhombic, Pbcn	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2n 2ab	Cell parameters from 29242 reflections
a = 36.2497 (7) Å	θ = 3.7–68.2°
b = 9.9940 (2) Å	µ = 8.05 mm⁻¹
c = 8.9392 (2) Å	T = 173 K
V = 3238.49 (12) Å³	Prism, yellow
Z = 4	0.3 × 0.3 × 0.1 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2964 independent reflections
Radiation source: fine-focus sealed tube	2439 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
Detector resolution: 10.000 pixels mm^-1	θ_max = 68.3°, θ_min = 4.6°
ω scans	h = −42→43
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	k = −11→12
T_min = 0.325, T_max = 0.448	l = −10→10
10761 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0606P)²] where P = (F_o² + 2F_c²)/3
2964 reflections	(Δ/σ)_max = 0.001
195 parameters	Δρ_max = 1.36 e Å⁻³
0 restraints	Δρ_min = −0.52 e Å⁻³

Crystal data top

[Cd(C₁₇H₁₅N₂S₂)₂]	V = 3238.49 (12) Å³
M_r = 735.26	Z = 4
Orthorhombic, Pbcn	Cu Kα radiation
a = 36.2497 (7) Å	µ = 8.05 mm⁻¹
b = 9.9940 (2) Å	T = 173 K
c = 8.9392 (2) Å	0.3 × 0.3 × 0.1 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	2964 independent reflections
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	2439 reflections with I > 2σ(I)
T_min = 0.325, T_max = 0.448	R_int = 0.079
10761 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.02	Δρ_max = 1.36 e Å⁻³
2964 reflections	Δρ_min = −0.52 e Å⁻³
195 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cd	0.5000	0.44301 (4)	0.7500	0.04150 (16)
N1	0.52779 (6)	0.2994 (3)	0.9175 (3)	0.0358 (6)
N2	0.56616 (6)	0.2968 (3)	0.9179 (3)	0.0367 (6)
S1	0.56402 (2)	0.50756 (11)	0.71527 (10)	0.0483 (3)
S2	0.62987 (2)	0.39583 (11)	0.83639 (11)	0.0540 (3)
C1	0.51250 (9)	0.2128 (3)	1.0048 (3)	0.0398 (7)
H1	0.5276	0.1511	1.0578	0.048*
C2	0.47320 (8)	0.2078 (3)	1.0235 (3)	0.0395 (7)
H2	0.4587	0.2715	0.9710	0.047*
C3	0.45573 (8)	0.1191 (4)	1.1103 (4)	0.0415 (8)
H3	0.4705	0.0526	1.1570	0.050*
C4	0.41607 (8)	0.1147 (3)	1.1403 (3)	0.0381 (7)
C5	0.39164 (8)	0.2100 (4)	1.0849 (4)	0.0436 (8)
H5	0.4007	0.2808	1.0244	0.052*
C6	0.35458 (8)	0.2033 (4)	1.1162 (4)	0.0476 (9)
H6	0.3383	0.2695	1.0779	0.057*
C7	0.34086 (9)	0.1000 (4)	1.2038 (4)	0.0511 (9)
H7	0.3152	0.0949	1.2243	0.061*
C8	0.36437 (11)	0.0055 (5)	1.2607 (4)	0.0516 (10)
H8	0.3550	−0.0643	1.3220	0.062*
C9	0.40186 (10)	0.0116 (5)	1.2288 (4)	0.0455 (8)
H9	0.4180	−0.0550	1.2675	0.055*
C10	0.58178 (8)	0.3856 (3)	0.8347 (3)	0.0391 (7)
C11	0.64403 (8)	0.2893 (4)	0.9912 (4)	0.0455 (8)
H11A	0.6300	0.3118	1.0829	0.055*
H11B	0.6399	0.1939	0.9668	0.055*
C12	0.68464 (8)	0.3169 (3)	1.0126 (3)	0.0413 (8)
C13	0.69639 (9)	0.4203 (4)	1.1010 (5)	0.0577 (10)
H13	0.6787	0.4747	1.1506	0.069*
C14	0.73377 (10)	0.4472 (4)	1.1193 (5)	0.0619 (12)
H14	0.7415	0.5188	1.1818	0.074*
C15	0.75932 (9)	0.3706 (4)	1.0474 (4)	0.0538 (10)
H15	0.7849	0.3884	1.0598	0.065*
C16	0.74806 (8)	0.2689 (4)	0.9579 (5)	0.0593 (10)
H16	0.7659	0.2167	0.9065	0.071*
C17	0.71095 (8)	0.2401 (4)	0.9404 (4)	0.0517 (9)
H17	0.7035	0.1675	0.8787	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.0334 (2)	0.0470 (3)	0.0440 (2)	0.000	−0.01208 (12)	0.000
N1	0.0262 (12)	0.0447 (16)	0.0365 (13)	0.0008 (11)	−0.0011 (10)	0.0027 (12)
N2	0.0255 (12)	0.0478 (17)	0.0368 (13)	0.0013 (11)	0.0000 (10)	0.0006 (12)
S1	0.0401 (5)	0.0524 (6)	0.0525 (5)	−0.0107 (4)	−0.0125 (4)	0.0125 (4)
S2	0.0278 (4)	0.0780 (7)	0.0562 (5)	−0.0073 (4)	0.0006 (3)	0.0214 (5)
C1	0.0286 (14)	0.050 (2)	0.0411 (16)	0.0016 (14)	−0.0024 (13)	0.0023 (15)
C2	0.0269 (14)	0.051 (2)	0.0408 (16)	0.0021 (14)	−0.0023 (12)	0.0052 (15)
C3	0.0308 (16)	0.052 (2)	0.0422 (17)	0.0037 (14)	−0.0054 (13)	0.0017 (15)
C4	0.0285 (15)	0.049 (2)	0.0368 (16)	−0.0030 (13)	−0.0014 (12)	−0.0023 (14)
C5	0.0337 (16)	0.049 (2)	0.0481 (18)	−0.0035 (14)	0.0000 (14)	0.0018 (16)
C6	0.0289 (16)	0.056 (2)	0.058 (2)	−0.0016 (15)	−0.0051 (14)	−0.0033 (18)
C7	0.0328 (18)	0.068 (3)	0.053 (2)	−0.0074 (17)	0.0038 (16)	−0.013 (2)
C8	0.044 (2)	0.058 (3)	0.054 (2)	−0.013 (2)	0.0063 (14)	0.0020 (17)
C9	0.0410 (19)	0.047 (2)	0.0486 (19)	0.0003 (17)	−0.0010 (14)	0.0020 (16)
C10	0.0301 (15)	0.049 (2)	0.0382 (16)	−0.0005 (14)	−0.0046 (12)	0.0002 (15)
C11	0.0256 (15)	0.060 (2)	0.0504 (19)	0.0024 (14)	0.0032 (13)	0.0102 (17)
C12	0.0256 (15)	0.055 (2)	0.0438 (17)	0.0007 (13)	0.0037 (12)	0.0050 (16)
C13	0.0376 (19)	0.071 (3)	0.065 (3)	0.0062 (17)	0.0113 (17)	−0.014 (2)
C14	0.046 (2)	0.075 (3)	0.065 (3)	−0.0093 (19)	−0.0016 (18)	−0.017 (2)
C15	0.0273 (16)	0.077 (3)	0.057 (2)	−0.0049 (17)	−0.0021 (15)	0.004 (2)
C16	0.0286 (18)	0.068 (3)	0.081 (3)	0.0077 (17)	0.0040 (16)	−0.010 (2)
C17	0.0330 (17)	0.054 (2)	0.068 (2)	0.0011 (15)	0.0028 (16)	−0.0126 (19)

Geometric parameters (Å, º) top

Cd—N1ⁱ	2.306 (2)	C6—H6	0.9500
Cd—N1	2.306 (2)	C7—C8	1.370 (6)
Cd—S1	2.4285 (9)	C7—H7	0.9500
Cd—S1ⁱ	2.4285 (9)	C8—C9	1.390 (5)
N1—C1	1.291 (4)	C8—H8	0.9500
N1—N2	1.391 (3)	C9—H9	0.9500
N2—C10	1.288 (4)	C11—C12	1.510 (4)
S1—C10	1.744 (3)	C11—H11A	0.9900
S2—C10	1.746 (3)	C11—H11B	0.9900
S2—C11	1.819 (3)	C12—C13	1.368 (5)
C1—C2	1.435 (4)	C12—C17	1.384 (4)
C1—H1	0.9500	C13—C14	1.391 (4)
C2—C3	1.337 (4)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.362 (5)
C3—C4	1.463 (4)	C14—H14	0.9500
C3—H3	0.9500	C15—C16	1.356 (5)
C4—C5	1.392 (4)	C15—H15	0.9500
C4—C9	1.398 (5)	C16—C17	1.385 (4)
C5—C6	1.374 (4)	C16—H16	0.9500
C5—H5	0.9500	C17—H17	0.9500
C6—C7	1.388 (5)

N1ⁱ—Cd—N1	103.00 (12)	C7—C8—C9	120.2 (4)
N1ⁱ—Cd—S1	119.99 (6)	C7—C8—H8	119.9
N1—Cd—S1	80.27 (6)	C9—C8—H8	119.9
N1ⁱ—Cd—S1ⁱ	80.27 (6)	C8—C9—C4	120.6 (4)
N1—Cd—S1ⁱ	119.99 (6)	C8—C9—H9	119.7
S1—Cd—S1ⁱ	149.19 (5)	C4—C9—H9	119.7
C1—N1—N2	114.6 (2)	N2—C10—S1	132.2 (2)
C1—N1—Cd	128.5 (2)	N2—C10—S2	118.3 (2)
N2—N1—Cd	116.73 (17)	S1—C10—S2	109.45 (17)
C10—N2—N1	115.2 (2)	C12—C11—S2	105.4 (2)
C10—S1—Cd	95.10 (11)	C12—C11—H11A	110.7
C10—S2—C11	104.71 (14)	S2—C11—H11A	110.7
N1—C1—C2	121.3 (3)	C12—C11—H11B	110.7
N1—C1—H1	119.3	S2—C11—H11B	110.7
C2—C1—H1	119.3	H11A—C11—H11B	108.8
C3—C2—C1	124.1 (3)	C13—C12—C17	118.2 (3)
C3—C2—H2	117.9	C13—C12—C11	121.0 (3)
C1—C2—H2	117.9	C17—C12—C11	120.8 (3)
C2—C3—C4	126.3 (3)	C12—C13—C14	121.1 (3)
C2—C3—H3	116.9	C12—C13—H13	119.4
C4—C3—H3	116.9	C14—C13—H13	119.4
C5—C4—C9	118.1 (3)	C15—C14—C13	119.9 (4)
C5—C4—C3	122.7 (3)	C15—C14—H14	120.1
C9—C4—C3	119.2 (3)	C13—C14—H14	120.1
C6—C5—C4	121.1 (3)	C16—C15—C14	119.6 (3)
C6—C5—H5	119.5	C16—C15—H15	120.2
C4—C5—H5	119.5	C14—C15—H15	120.2
C5—C6—C7	120.1 (3)	C15—C16—C17	121.0 (3)
C5—C6—H6	119.9	C15—C16—H16	119.5
C7—C6—H6	119.9	C17—C16—H16	119.5
C8—C7—C6	119.9 (3)	C12—C17—C16	120.1 (3)
C8—C7—H7	120.0	C12—C17—H17	119.9
C6—C7—H7	120.0	C16—C17—H17	119.9

N1ⁱ—Cd—N1—C1	−62.5 (2)	C6—C7—C8—C9	−1.1 (6)
S1—Cd—N1—C1	178.8 (3)	C7—C8—C9—C4	0.8 (6)
S1ⁱ—Cd—N1—C1	23.7 (3)	C5—C4—C9—C8	−0.3 (5)
N1ⁱ—Cd—N1—N2	111.98 (19)	C3—C4—C9—C8	179.3 (3)
S1—Cd—N1—N2	−6.76 (17)	N1—N2—C10—S1	−2.2 (4)
S1ⁱ—Cd—N1—N2	−161.87 (15)	N1—N2—C10—S2	176.47 (19)
C1—N1—N2—C10	−177.9 (3)	Cd—S1—C10—N2	−3.1 (3)
Cd—N1—N2—C10	6.8 (3)	Cd—S1—C10—S2	178.22 (14)
N1ⁱ—Cd—S1—C10	−95.26 (13)	C11—S2—C10—N2	−10.3 (3)
N1—Cd—S1—C10	4.21 (13)	C11—S2—C10—S1	168.62 (18)
S1ⁱ—Cd—S1—C10	138.83 (11)	C10—S2—C11—C12	−169.8 (2)
N2—N1—C1—C2	176.4 (2)	S2—C11—C12—C13	86.4 (3)
Cd—N1—C1—C2	−9.0 (4)	S2—C11—C12—C17	−92.0 (3)
N1—C1—C2—C3	178.8 (3)	C17—C12—C13—C14	−0.6 (6)
C1—C2—C3—C4	176.1 (3)	C11—C12—C13—C14	−179.1 (3)
C2—C3—C4—C5	−3.2 (5)	C12—C13—C14—C15	0.7 (6)
C2—C3—C4—C9	177.2 (3)	C13—C14—C15—C16	0.2 (6)
C9—C4—C5—C6	0.1 (5)	C14—C15—C16—C17	−1.1 (6)
C3—C4—C5—C6	−179.5 (3)	C13—C12—C17—C16	−0.2 (5)
C4—C5—C6—C7	−0.3 (5)	C11—C12—C17—C16	178.2 (3)
C5—C6—C7—C8	0.8 (5)	C15—C16—C17—C12	1.1 (6)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···S2ⁱⁱ	0.95	2.75	3.690 (4)	170

Symmetry code: (ii) x, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	[Cd(C₁₇H₁₅N₂S₂)₂]
M_r	735.26
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	173
a, b, c (Å)	36.2497 (7), 9.9940 (2), 8.9392 (2)
V (Å³)	3238.49 (12)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	8.05
Crystal size (mm)	0.3 × 0.3 × 0.1

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Rigaku, 1995)
T_min, T_max	0.325, 0.448
No. of measured, independent and observed [I > 2σ(I)] reflections	10761, 2964, 2439
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.115, 1.02
No. of reflections	2964
No. of parameters	195
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.36, −0.52

Computer programs: RAPID-AUTO (Rigaku, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), CrystalStructure (Rigaku, 2010), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Cd—N1	2.306 (2)	Cd—S1	2.4285 (9)

N1ⁱ—Cd—N1	103.00 (12)	N1—Cd—S1	80.27 (6)
N1ⁱ—Cd—S1	119.99 (6)	S1—Cd—S1ⁱ	149.19 (5)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···S2ⁱⁱ	0.95	2.75	3.690 (4)	170

Symmetry code: (ii) x, −y+1, z+1/2.

Acknowledgements

The authors MAAAAI and MSR are grateful to the Department of Chemistry, Rajshahi University of Engineering and Technology, for the provision of laboratory facilities. MTHT thanks the Department of Chemistry, Rajshahi University, for supplying the necessary chemicals. MCS acknowledges the Department of Chemistry, Toyama University, for providing funds for the X-ray single-crystal facility.

References

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