(2,2′-Bipyridine-κ2N,N′)bis­(N-isopropyl-N-methyl­dithio­carbamato-κ2S,S′)cadmium

Wahab, N.A.A.; Baba, I.; Mohamed Tahir, M.I.; Tiekink, E.R.T.

doi:10.1107/S1600536811012414

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages m551-m552

doi:10.1107/S1600536811012414

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(2,2′-Bipyridine-κ²N,N′)bis(N-isopropyl-N-methyldithiocarbamato-κ²S,S′)cadmium

Nor Asiken Abdul Wahab,^a Ibrahim Baba,^a ‡ Mohamed Ibrahim Mohamed Tahir ^b and Edward R. T. Tiekink ^c ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Malaysia, ^bDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 3 April 2011; accepted 4 April 2011; online 7 April 2011)

The Cd^II atom in the title compound, [Cd(C₅H₁₀NS₂)₂(C₁₀H₈N₂)], exists in an N₂S₄ donor set defined by two chelating dithiocarbamate anions as well as a 2,2′-bipyridine ligand. The coordination geometry approximates a trigonal prism. The crystal packing features weak C—H⋯S interactions, leading to linear supramolecular chains along the a axis. The primary connections between these are by π–π stacking interactions [ring centroid distance between centrosymmetrically related pyridyl rings = 3.7455 (10) Å]. Overall, the crystal structure may be described as comprising double layers of molecules that stack along the b axis.

Related literature

For related structures of pyridyl adducts of cadmium dithiocarbamtes, see: Song & Tiekink (2009 ); Broker & Tiekink (2011 ); Jamaluddin et al. (2011 ).

Experimental

Crystal data

[Cd(C₅H₁₀NS₂)₂(C₁₀H₈N₂)]
M_r = 565.10
Monoclinic, P 2₁ /n
a = 9.6061 (2) Å
b = 28.6277 (4) Å
c = 9.8187 (2) Å
β = 112.860 (2)°
V = 2488.07 (8) Å³
Z = 4
Mo Kα radiation
μ = 1.23 mm⁻¹
T = 150 K
0.17 × 0.13 × 0.05 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.853, T_max = 0.941
53095 measured reflections
5700 independent reflections
5013 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.053
S = 1.03
5700 reflections
268 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd—S1	2.6463 (5)
Cd—S2	2.7128 (5)
Cd—S3	2.6518 (5)
Cd—S4	2.6490 (5)
Cd—N3	2.4122 (14)
Cd—N4	2.4191 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯S2ⁱ	0.95	2.78	3.712 (2)	167
Symmetry code: (i) x-1, y, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811012414/hb5834sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811012414/hb5834Isup2.hkl

checkCIF report

Comment top

In continuation of systematic structural studies of various pyridyl adducts of cadmium dithiocarbamates (Song & Tiekink, 2009; Broker & Tiekink, 2011; Jamaluddin et al., 2011), the title compound Cd[S₂CN(Me)iPr)₂]₂(2,2'-bipyridine), (I), was investigated. The Cd^II atom is coordinated by two dithiocarbamate ligands, each essentially forming symmetric Cd—S bonds, and a symmetrically chelating 2,2'-bipyridine ligand, Fig. 1 and Table 1. The equivalence in the Cd—S bond distances is reflected in the narrow range of associated C≐S bond distances, i.e. 1.7168 (18) to 1.7290 (17) Å. A small twist is noted between the pyridyl rings of the 2,2'-bipyridine ligand as seen in the dihedral angle of 9.25 (9) ° formed between the rings. The N₂S₄ donor set defines a distorted trigonal prismatic geometry.

The crystal packing of (I) features linear supramolecular chains along the a axis that are sustained by C—H···S interactions, Fig. 2 and Table 2. Chains lie in the ac plane and inter-digitate via π–π interactions with centrosymmetrically related layers to form a double layer [ring centroid(N3-pyridyl)···ring centroid(N3-centroid)ⁱ = 3.7455 (10) Å for i: 2 - x, 1 - y, 1 - z]. Double layers stack along the b axis and are separated by hydrophobic interactions, Fig. 3.

Related literature top

For related structures of pyridyl adducts of cadmium dithiocarbamtes, see: Song & Tiekink (2009); Broker & Tiekink (2011); Jamaluddin et al. (2011).

Experimental top

The title compound was prepared using an in situ method by the addition of carbon disulfide (0.02 mol) to an ethanolic solution (20 ml) of methylisopropropylamine (0.02 mol) and 2,2-bipyridine (0.01 mol) in ethanol (20 ml). The mixture was stirred for 1 h at 277 K. The resulting solution was added drop-wise to a solution of cadmium(II) dichloride (0.01 mol) in ethanol (20 ml). The mixture was stirred 3 h. The yellowish precipitate was filtered, washed with cold ethanol and dried in a desiccator. Recrystallization was from ethanol:chloroform (1:2 v/v) to yield yellow prisms of (I). M.pt. 473.6–475.2 K. Elemental analysis. Found (calculated) for C₂₂H₃₂CdN₄S₄: C, 42.63 (42.51); H 4.48 (4.99); N 10.74 (9.91); S 21.80 (22.70) %. UV (CHCl₃) λ_max 283.5 and 261.0 nm (L(π) → L(π*)). IR (KBr): ν(C—H) 2928 s; ν(C≐N) 1565 s; ν(N—C) 1468 m; ν(C≐S) 970 s; ν(Cd—S) 381 s cm^-1.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view of the linear supramolecular chain long the a axis in (I) mediated by C—H···S interactions (orange dashed lines) along the a axis.
	Fig. 3. A view in projection down the a axis of the crystal packing in (I) highlighting the π–π interactions (shown as purple dashed lines).

(2,2'-Bipyridine-κ²N,N')bis(N-isopropyl- N-methyldithiocarbamato-κ²S,S')cadmium top

Crystal data top

[Cd(C₅H₁₀NS₂)₂(C₁₀H₈N₂)]	F(000) = 1152
M_r = 565.10	D_x = 1.509 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 26576 reflections
a = 9.6061 (2) Å	θ = 2–29°
b = 28.6277 (4) Å	µ = 1.23 mm⁻¹
c = 9.8187 (2) Å	T = 150 K
β = 112.860 (2)°	Prism, yellow
V = 2488.07 (8) Å³	0.17 × 0.13 × 0.05 mm
Z = 4

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	5700 independent reflections
Radiation source: fine-focus sealed tube	5013 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 16.1952 pixels mm^-1	θ_max = 27.5°, θ_min = 2.4°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −37→37
T_min = 0.853, T_max = 0.941	l = −12→12
53095 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.053	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.023P)² + 0.9719P] where P = (F_o² + 2F_c²)/3
5700 reflections	(Δ/σ)_max = 0.002
268 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Cd(C₅H₁₀NS₂)₂(C₁₀H₈N₂)]	V = 2488.07 (8) Å³
M_r = 565.10	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.6061 (2) Å	µ = 1.23 mm⁻¹
b = 28.6277 (4) Å	T = 150 K
c = 9.8187 (2) Å	0.17 × 0.13 × 0.05 mm
β = 112.860 (2)°

Data collection top

Oxford Diffraction Xcaliber Eos Gemini diffractometer	5700 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	5013 reflections with I > 2σ(I)
T_min = 0.853, T_max = 0.941	R_int = 0.048
53095 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.053	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
5700 reflections	Δρ_min = −0.30 e Å⁻³
268 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	1.074719 (14)	0.619541 (4)	0.837624 (13)	0.02469 (5)
S1	1.13178 (5)	0.638504 (17)	1.11803 (5)	0.02979 (10)
S2	1.37352 (5)	0.615697 (17)	1.01159 (5)	0.03243 (10)
S3	0.88132 (5)	0.688040 (16)	0.71256 (5)	0.03348 (11)
S4	1.10292 (5)	0.651618 (17)	0.59657 (5)	0.03368 (11)
N1	1.42420 (16)	0.63344 (5)	1.29241 (16)	0.0285 (3)
N2	0.91865 (17)	0.72387 (5)	0.47972 (17)	0.0313 (3)
N3	1.09345 (17)	0.54076 (5)	0.75929 (16)	0.0282 (3)
N4	0.87517 (16)	0.56931 (5)	0.84481 (16)	0.0292 (3)
C1	1.32019 (19)	0.62947 (6)	1.15504 (19)	0.0254 (3)
C2	1.5853 (2)	0.63217 (9)	1.3206 (2)	0.0448 (5)
H2A	1.6125	0.6009	1.2987	0.067*
H2B	1.6444	0.6397	1.4245	0.067*
H2C	1.6070	0.6551	1.2573	0.067*
C3	1.3829 (2)	0.64480 (7)	1.41991 (19)	0.0296 (4)
H3	1.2720	0.6392	1.3881	0.036*
C4	1.4639 (3)	0.61310 (9)	1.5506 (3)	0.0521 (6)
H4A	1.4428	0.5804	1.5198	0.078*
H4B	1.4281	0.6196	1.6296	0.078*
H4C	1.5729	0.6188	1.5870	0.078*
C5	1.4115 (2)	0.69603 (7)	1.4595 (2)	0.0414 (5)
H5A	1.5206	0.7020	1.5016	0.062*
H5B	1.3688	0.7042	1.5322	0.062*
H5C	1.3637	0.7151	1.3705	0.062*
C6	0.96267 (19)	0.69114 (6)	0.58500 (19)	0.0253 (3)
C7	0.7956 (2)	0.75621 (7)	0.4673 (3)	0.0439 (5)
H7A	0.7009	0.7388	0.4401	0.066*
H7B	0.7853	0.7796	0.3912	0.066*
H7C	0.8185	0.7718	0.5624	0.066*
C8	0.9824 (2)	0.72780 (7)	0.3644 (2)	0.0374 (5)
H8	1.0722	0.7067	0.3931	0.045*
C9	1.0361 (3)	0.77737 (8)	0.3560 (2)	0.0491 (6)
H9A	0.9485	0.7980	0.3128	0.074*
H9B	1.0953	0.7777	0.2942	0.074*
H9C	1.0991	0.7883	0.4557	0.074*
C10	0.8681 (3)	0.71105 (8)	0.2173 (2)	0.0455 (5)
H10A	0.8415	0.6785	0.2264	0.068*
H10B	0.9116	0.7133	0.1423	0.068*
H10C	0.7772	0.7305	0.1880	0.068*
C11	1.1989 (2)	0.52925 (7)	0.7083 (2)	0.0359 (4)
H11	1.2712	0.5522	0.7104	0.043*
C12	1.2078 (2)	0.48551 (7)	0.6527 (2)	0.0405 (5)
H12	1.2837	0.4786	0.6162	0.049*
C13	1.1038 (2)	0.45225 (7)	0.6515 (2)	0.0405 (5)
H13	1.1069	0.4218	0.6140	0.049*
C14	0.9948 (2)	0.46353 (6)	0.7053 (2)	0.0349 (4)
H14	0.9226	0.4409	0.7059	0.042*
C15	0.99217 (19)	0.50838 (6)	0.75862 (18)	0.0269 (4)
C16	0.87718 (19)	0.52370 (6)	0.81662 (18)	0.0265 (4)
C17	0.7754 (2)	0.58528 (7)	0.8983 (2)	0.0355 (4)
H17	0.7746	0.6177	0.9183	0.043*
C18	0.6735 (2)	0.55653 (8)	0.9256 (2)	0.0394 (5)
H18	0.6034	0.5689	0.9627	0.047*
C19	0.6762 (2)	0.50964 (8)	0.8977 (2)	0.0436 (5)
H19	0.6081	0.4890	0.9161	0.052*
C20	0.7787 (2)	0.49272 (7)	0.8427 (2)	0.0387 (4)
H20	0.7819	0.4603	0.8230	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.02824 (7)	0.02325 (7)	0.02276 (7)	0.00063 (5)	0.01010 (5)	0.00100 (5)
S1	0.0242 (2)	0.0389 (3)	0.0253 (2)	0.00347 (18)	0.00845 (17)	−0.00182 (18)
S2	0.0316 (2)	0.0385 (3)	0.0299 (2)	0.00315 (19)	0.01483 (19)	−0.00517 (19)
S3	0.0408 (3)	0.0309 (2)	0.0352 (3)	0.0088 (2)	0.0218 (2)	0.00636 (19)
S4	0.0373 (2)	0.0349 (2)	0.0347 (2)	0.01276 (19)	0.0204 (2)	0.01318 (19)
N1	0.0226 (7)	0.0347 (8)	0.0274 (8)	−0.0005 (6)	0.0089 (6)	−0.0037 (6)
N2	0.0307 (8)	0.0292 (8)	0.0381 (9)	0.0075 (6)	0.0177 (7)	0.0115 (6)
N3	0.0329 (8)	0.0267 (8)	0.0280 (8)	0.0006 (6)	0.0150 (6)	0.0020 (6)
N4	0.0288 (8)	0.0293 (8)	0.0291 (8)	0.0015 (6)	0.0108 (6)	0.0016 (6)
C1	0.0267 (8)	0.0203 (8)	0.0291 (9)	−0.0001 (6)	0.0109 (7)	0.0008 (6)
C2	0.0228 (9)	0.0629 (14)	0.0460 (12)	0.0012 (9)	0.0103 (9)	−0.0117 (10)
C3	0.0255 (8)	0.0390 (10)	0.0239 (9)	0.0000 (7)	0.0091 (7)	0.0016 (7)
C4	0.0520 (14)	0.0628 (15)	0.0412 (13)	0.0102 (11)	0.0177 (11)	0.0200 (11)
C5	0.0482 (12)	0.0441 (12)	0.0366 (11)	−0.0062 (9)	0.0217 (9)	−0.0101 (9)
C6	0.0257 (8)	0.0213 (8)	0.0284 (9)	−0.0028 (6)	0.0099 (7)	−0.0003 (7)
C7	0.0452 (12)	0.0355 (11)	0.0595 (14)	0.0161 (9)	0.0297 (11)	0.0192 (10)
C8	0.0332 (10)	0.0431 (11)	0.0405 (11)	0.0109 (8)	0.0191 (9)	0.0195 (9)
C9	0.0434 (12)	0.0626 (15)	0.0373 (12)	−0.0150 (11)	0.0115 (10)	0.0146 (10)
C10	0.0553 (13)	0.0397 (12)	0.0475 (13)	0.0006 (10)	0.0265 (11)	0.0006 (9)
C11	0.0420 (11)	0.0308 (10)	0.0415 (11)	0.0001 (8)	0.0234 (9)	0.0012 (8)
C12	0.0468 (12)	0.0376 (11)	0.0445 (12)	0.0083 (9)	0.0259 (10)	0.0009 (9)
C13	0.0465 (12)	0.0287 (10)	0.0446 (12)	0.0072 (9)	0.0160 (10)	−0.0030 (8)
C14	0.0350 (10)	0.0259 (9)	0.0404 (11)	−0.0001 (8)	0.0110 (8)	−0.0009 (8)
C15	0.0291 (9)	0.0249 (9)	0.0231 (8)	0.0017 (7)	0.0061 (7)	0.0044 (7)
C16	0.0248 (8)	0.0267 (9)	0.0248 (9)	0.0025 (7)	0.0062 (7)	0.0052 (7)
C17	0.0343 (10)	0.0365 (10)	0.0370 (11)	0.0046 (8)	0.0154 (8)	0.0001 (8)
C18	0.0298 (10)	0.0513 (13)	0.0397 (11)	0.0089 (9)	0.0164 (8)	0.0089 (9)
C19	0.0337 (10)	0.0461 (12)	0.0551 (13)	0.0011 (9)	0.0216 (10)	0.0161 (10)
C20	0.0355 (10)	0.0303 (10)	0.0513 (12)	0.0015 (8)	0.0181 (9)	0.0084 (9)

Geometric parameters (Å, º) top

Cd—S1	2.6463 (5)	C5—H5C	0.9800
Cd—S2	2.7128 (5)	C7—H7A	0.9800
Cd—S3	2.6518 (5)	C7—H7B	0.9800
Cd—S4	2.6490 (5)	C7—H7C	0.9800
Cd—N3	2.4122 (14)	C8—C10	1.512 (3)
Cd—N4	2.4191 (15)	C8—C9	1.523 (3)
S1—C1	1.7215 (18)	C8—H8	1.0000
S2—C1	1.7212 (18)	C9—H9A	0.9800
S3—C6	1.7168 (18)	C9—H9B	0.9800
S4—C6	1.7290 (17)	C9—H9C	0.9800
N1—C1	1.335 (2)	C10—H10A	0.9800
N1—C2	1.463 (2)	C10—H10B	0.9800
N1—C3	1.488 (2)	C10—H10C	0.9800
N2—C6	1.336 (2)	C11—C12	1.382 (3)
N2—C7	1.469 (2)	C11—H11	0.9500
N2—C8	1.486 (2)	C12—C13	1.377 (3)
N3—C11	1.334 (2)	C12—H12	0.9500
N3—C15	1.342 (2)	C13—C14	1.382 (3)
N4—C16	1.337 (2)	C13—H13	0.9500
N4—C17	1.340 (2)	C14—C15	1.390 (2)
C2—H2A	0.9800	C14—H14	0.9500
C2—H2B	0.9800	C15—C16	1.492 (2)
C2—H2C	0.9800	C16—C20	1.391 (3)
C3—C5	1.515 (3)	C17—C18	1.382 (3)
C3—C4	1.516 (3)	C17—H17	0.9500
C3—H3	1.0000	C18—C19	1.372 (3)
C4—H4A	0.9800	C18—H18	0.9500
C4—H4B	0.9800	C19—C20	1.382 (3)
C4—H4C	0.9800	C19—H19	0.9500
C5—H5A	0.9800	C20—H20	0.9500
C5—H5B	0.9800

N3—Cd—N4	67.15 (5)	N2—C6—S3	120.24 (13)
N3—Cd—S1	120.84 (4)	N2—C6—S4	120.93 (13)
N4—Cd—S1	86.43 (4)	S3—C6—S4	118.83 (10)
N3—Cd—S4	89.60 (4)	N2—C7—H7A	109.5
N4—Cd—S4	126.11 (4)	N2—C7—H7B	109.5
S1—Cd—S4	143.780 (17)	H7A—C7—H7B	109.5
N3—Cd—S3	132.02 (4)	N2—C7—H7C	109.5
N4—Cd—S3	91.86 (4)	H7A—C7—H7C	109.5
S1—Cd—S3	98.905 (15)	H7B—C7—H7C	109.5
S4—Cd—S3	68.057 (14)	N2—C8—C10	110.03 (16)
N3—Cd—S2	88.34 (4)	N2—C8—C9	111.10 (17)
N4—Cd—S2	127.89 (4)	C10—C8—C9	112.31 (16)
S1—Cd—S2	67.192 (14)	N2—C8—H8	107.7
S4—Cd—S2	97.251 (15)	C10—C8—H8	107.7
S3—Cd—S2	134.517 (16)	C9—C8—H8	107.7
C1—S1—Cd	87.98 (6)	C8—C9—H9A	109.5
C1—S2—Cd	85.84 (6)	C8—C9—H9B	109.5
C6—S3—Cd	86.59 (6)	H9A—C9—H9B	109.5
C6—S4—Cd	86.44 (6)	C8—C9—H9C	109.5
C1—N1—C2	120.67 (15)	H9A—C9—H9C	109.5
C1—N1—C3	121.93 (14)	H9B—C9—H9C	109.5
C2—N1—C3	117.02 (14)	C8—C10—H10A	109.5
C6—N2—C7	120.58 (15)	C8—C10—H10B	109.5
C6—N2—C8	122.85 (15)	H10A—C10—H10B	109.5
C7—N2—C8	116.46 (14)	C8—C10—H10C	109.5
C11—N3—C15	118.85 (16)	H10A—C10—H10C	109.5
C11—N3—Cd	120.81 (12)	H10B—C10—H10C	109.5
C15—N3—Cd	120.24 (11)	N3—C11—C12	123.01 (18)
C16—N4—C17	118.99 (16)	N3—C11—H11	118.5
C16—N4—Cd	119.95 (11)	C12—C11—H11	118.5
C17—N4—Cd	120.30 (12)	C13—C12—C11	118.27 (19)
N1—C1—S2	120.15 (13)	C13—C12—H12	120.9
N1—C1—S1	120.87 (13)	C11—C12—H12	120.9
S2—C1—S1	118.97 (10)	C12—C13—C14	119.36 (18)
N1—C2—H2A	109.5	C12—C13—H13	120.3
N1—C2—H2B	109.5	C14—C13—H13	120.3
H2A—C2—H2B	109.5	C13—C14—C15	119.15 (18)
N1—C2—H2C	109.5	C13—C14—H14	120.4
H2A—C2—H2C	109.5	C15—C14—H14	120.4
H2B—C2—H2C	109.5	N3—C15—C14	121.37 (17)
N1—C3—C5	110.28 (15)	N3—C15—C16	115.97 (15)
N1—C3—C4	111.39 (16)	C14—C15—C16	122.66 (16)
C5—C3—C4	112.32 (17)	N4—C16—C20	121.27 (17)
N1—C3—H3	107.5	N4—C16—C15	116.02 (15)
C5—C3—H3	107.5	C20—C16—C15	122.70 (16)
C4—C3—H3	107.5	N4—C17—C18	122.76 (19)
C3—C4—H4A	109.5	N4—C17—H17	118.6
C3—C4—H4B	109.5	C18—C17—H17	118.6
H4A—C4—H4B	109.5	C19—C18—C17	118.32 (19)
C3—C4—H4C	109.5	C19—C18—H18	120.8
H4A—C4—H4C	109.5	C17—C18—H18	120.8
H4B—C4—H4C	109.5	C18—C19—C20	119.48 (19)
C3—C5—H5A	109.5	C18—C19—H19	120.3
C3—C5—H5B	109.5	C20—C19—H19	120.3
H5A—C5—H5B	109.5	C19—C20—C16	119.17 (19)
C3—C5—H5C	109.5	C19—C20—H20	120.4
H5A—C5—H5C	109.5	C16—C20—H20	120.4
H5B—C5—H5C	109.5

N3—Cd—S1—C1	72.53 (7)	Cd—S2—C1—S1	−1.23 (9)
N4—Cd—S1—C1	133.16 (7)	Cd—S1—C1—N1	−179.36 (14)
S4—Cd—S1—C1	−70.74 (6)	Cd—S1—C1—S2	1.26 (9)
S3—Cd—S1—C1	−135.51 (6)	C1—N1—C3—C5	−100.74 (19)
S2—Cd—S1—C1	−0.76 (6)	C2—N1—C3—C5	72.2 (2)
N3—Cd—S2—C1	−123.88 (7)	C1—N1—C3—C4	133.84 (18)
N4—Cd—S2—C1	−64.86 (7)	C2—N1—C3—C4	−53.2 (2)
S1—Cd—S2—C1	0.76 (6)	C7—N2—C6—S3	−2.8 (2)
S4—Cd—S2—C1	146.73 (6)	C8—N2—C6—S3	−178.74 (14)
S3—Cd—S2—C1	80.51 (6)	C7—N2—C6—S4	177.74 (15)
N3—Cd—S3—C6	−69.81 (7)	C8—N2—C6—S4	1.8 (2)
N4—Cd—S3—C6	−130.23 (7)	Cd—S3—C6—N2	−176.65 (14)
S1—Cd—S3—C6	143.09 (6)	Cd—S3—C6—S4	2.79 (9)
S4—Cd—S3—C6	−1.72 (6)	Cd—S4—C6—N2	176.64 (14)
S2—Cd—S3—C6	76.43 (6)	Cd—S4—C6—S3	−2.79 (9)
N3—Cd—S4—C6	138.13 (7)	C6—N2—C8—C10	106.5 (2)
N4—Cd—S4—C6	77.20 (7)	C7—N2—C8—C10	−69.5 (2)
S1—Cd—S4—C6	−72.77 (6)	C6—N2—C8—C9	−128.48 (19)
S3—Cd—S4—C6	1.71 (6)	C7—N2—C8—C9	55.5 (2)
S2—Cd—S4—C6	−133.59 (6)	C15—N3—C11—C12	0.9 (3)
N4—Cd—N3—C11	175.46 (15)	Cd—N3—C11—C12	−175.40 (15)
S1—Cd—N3—C11	−113.83 (13)	N3—C11—C12—C13	−0.7 (3)
S4—Cd—N3—C11	45.48 (14)	C11—C12—C13—C14	0.0 (3)
S3—Cd—N3—C11	104.86 (14)	C12—C13—C14—C15	0.4 (3)
S2—Cd—N3—C11	−51.79 (14)	C11—N3—C15—C14	−0.4 (3)
N4—Cd—N3—C15	−0.80 (12)	Cd—N3—C15—C14	175.94 (13)
S1—Cd—N3—C15	69.92 (13)	C11—N3—C15—C16	−179.77 (16)
S4—Cd—N3—C15	−130.78 (12)	Cd—N3—C15—C16	−3.45 (19)
S3—Cd—N3—C15	−71.39 (13)	C13—C14—C15—N3	−0.3 (3)
S2—Cd—N3—C15	131.96 (12)	C13—C14—C15—C16	179.07 (17)
N3—Cd—N4—C16	5.64 (12)	C17—N4—C16—C20	−0.5 (3)
S1—Cd—N4—C16	−120.06 (12)	Cd—N4—C16—C20	169.56 (13)
S4—Cd—N4—C16	77.17 (13)	C17—N4—C16—C15	−179.46 (15)
S3—Cd—N4—C16	141.13 (12)	Cd—N4—C16—C15	−9.43 (19)
S2—Cd—N4—C16	−62.79 (14)	N3—C15—C16—N4	8.4 (2)
N3—Cd—N4—C17	175.54 (15)	C14—C15—C16—N4	−171.00 (16)
S1—Cd—N4—C17	49.84 (13)	N3—C15—C16—C20	−170.60 (16)
S4—Cd—N4—C17	−112.93 (13)	C14—C15—C16—C20	10.0 (3)
S3—Cd—N4—C17	−48.97 (14)	C16—N4—C17—C18	−0.1 (3)
S2—Cd—N4—C17	107.11 (13)	Cd—N4—C17—C18	−170.09 (14)
C2—N1—C1—S2	7.9 (2)	N4—C17—C18—C19	0.6 (3)
C3—N1—C1—S2	−179.35 (13)	C17—C18—C19—C20	−0.5 (3)
C2—N1—C1—S1	−171.46 (15)	C18—C19—C20—C16	−0.1 (3)
C3—N1—C1—S1	1.3 (2)	N4—C16—C20—C19	0.5 (3)
Cd—S2—C1—N1	179.38 (14)	C15—C16—C20—C19	179.47 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···S2ⁱ	0.95	2.78	3.712 (2)	167

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	[Cd(C₅H₁₀NS₂)₂(C₁₀H₈N₂)]
M_r	565.10
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	9.6061 (2), 28.6277 (4), 9.8187 (2)
β (°)	112.860 (2)
V (Å³)	2488.07 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.23
Crystal size (mm)	0.17 × 0.13 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.853, 0.941
No. of measured, independent and observed [I > 2σ(I)] reflections	53095, 5700, 5013
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.053, 1.03
No. of reflections	5700
No. of parameters	268
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.30

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Cd—S1	2.6463 (5)	Cd—S4	2.6490 (5)
Cd—S2	2.7128 (5)	Cd—N3	2.4122 (14)
Cd—S3	2.6518 (5)	Cd—N4	2.4191 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···S2ⁱ	0.95	2.78	3.712 (2)	167

Symmetry code: (i) x−1, y, z.

Footnotes

‡Additional correspondence author, e-mail: aibi@ukm.my.

Acknowledgements

The authors thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08–27-111), the Ministry of Higher Education (UKM-ST-06-FRGS0092–2010), Universiti Putra Malaysia and the University of Malaya for supporting this study.

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Broker, G. A. & Tiekink, E. R. T. (2011). Acta Cryst. E67, m320–m321. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Jamaluddin, N. A., Baba, I., Mohamed Tahir, M. I. & Tiekink, E. R. T. (2011). Acta Cryst. E67, m384–m385. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Song, J. C. & Tiekink, E. R. T. (2009). Acta Cryst. E65, m1669–m1670. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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