(2,2′-Bipyridine-κ2N,N′)bis­(N-ethyl-N-phenyl­dithio­carbamato-κ2S,S′)cadmium(II) chloro­form solvate

Baba, I.; Nik Intan, N.I.; Yamin, B.M.; Ng, S.W.

doi:10.1107/S1600536809041294

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1364

https://doi.org/10.1107/S1600536809041294

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(2,2′-Bipyridine-κ²N,N′)bis(N-ethyl-N-phenyldithiocarbamato-κ²S,S′)cadmium(II) chloroform solvate

Ibrahim Baba,^a Nik Ismail Nik Intan,^a Bohari M. Yamin ^a and Seik Weng Ng ^b ^*

^aSchool of Chemical Sciences, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor Darul Ehsan, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 9 October 2009; accepted 9 October 2009; online 17 October 2009)

In the title compound, [Cd(C₉H₁₀NS₂)₂(C₁₀H₈N₂)]·CHCl₃, the Cd^II atom exists in an all-cis distorted octahedral geometry. Chelation is isobidentate for one dithiocarbamate ligand and anisobidentate for the other. The chloroform solvent molecule is disordered over two positions of equal occupancy.

Related literature

For the crystal structures of other cadmium dithiocarbamate–2,2′-bipyridine adducts, see: Airoldi et al. (1990 ); Deng et al. (2007 ); Ivanchenko et al. (2000 ).

Experimental

Crystal data

[Cd(C₉H₁₀NS₂)₂(C₁₀H₈N₂)]·CHCl₃
M_r = 780.55
Monoclinic, P 2₁ /c
a = 7.1911 (6) Å
b = 27.752 (3) Å
c = 17.1907 (16) Å
β = 99.620 (5)°
V = 3382.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.16 mm⁻¹
T = 293 K
0.23 × 0.06 × 0.01 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.777, T_max = 0.989
18956 measured reflections
5964 independent reflections
4307 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.170
S = 1.31
5964 reflections
358 parameters
76 restraints
H-atom parameters constrained
Δρ_max = 0.85 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536809041294/xu2633sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809041294/xu2633Isup2.hkl

checkCIF report

Related literature top

For the crystal structures of other cadmium dithiocarbamate–2,2'-bipyridine adducts, see: Airoldi et al. (1990); Deng et al. (2007); Ivanchenko et al. (2000).

Experimental top

Ethylphenylamine (20 mmol) and carbon disulfide (20 mmol) were dissolved in ethanol (50 ml) at 277 K. Calcium chloride (10 mmol) and 2,2'-bipyridine (10 mmol) dissolved in ethanol (50 mmol) was then added. The white solid that precipitated was collected and recrystallized from an ethanol-chloroform mixture.

Structure description top

For the crystal structures of other cadmium dithiocarbamate–2,2'-bipyridine adducts, see: Airoldi et al. (1990); Deng et al. (2007); Ivanchenko et al. (2000).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Cd(C₁₀H₈N₂)(C₉H₁₀NS₂)₂^.CHCl₃ at the 50% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.

(2,2'-Bipyridine-κ²N,N')bis(N-ethyl-N- phenyldithiocarbamato-κ²S,S')cadmium(II) chloroform solvate top

Crystal data top

[Cd(C₉H₁₀NS₂)₂(C₁₀H₈N₂)]·CHCl₃	F(000) = 1576
M_r = 780.55	D_x = 1.533 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2492 reflections
a = 7.1911 (6) Å	θ = 2.5–20.1°
b = 27.752 (3) Å	µ = 1.16 mm⁻¹
c = 17.1907 (16) Å	T = 293 K
β = 99.620 (5)°	Plate, yellow
V = 3382.5 (6) Å³	0.23 × 0.06 × 0.01 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5964 independent reflections
Radiation source: fine-focus sealed tube	4307 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
Detector resolution: 8.33 pixels mm^-1	θ_max = 25.0°, θ_min = 1.4°
φ and ω scans	h = −8→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −27→33
T_min = 0.777, T_max = 0.989	l = −20→20
18956 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.170	H-atom parameters constrained
S = 1.31	w = 1/[σ²(F_o²) + (0.05P)² + 5.0P] where P = (F_o² + 2F_c²)/3
5964 reflections	(Δ/σ)_max = 0.001
358 parameters	Δρ_max = 0.85 e Å⁻³
76 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Cd(C₉H₁₀NS₂)₂(C₁₀H₈N₂)]·CHCl₃	V = 3382.5 (6) Å³
M_r = 780.55	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.1911 (6) Å	µ = 1.16 mm⁻¹
b = 27.752 (3) Å	T = 293 K
c = 17.1907 (16) Å	0.23 × 0.06 × 0.01 mm
β = 99.620 (5)°

Data collection top

Bruker SMART APEX diffractometer	5964 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4307 reflections with I > 2σ(I)
T_min = 0.777, T_max = 0.989	R_int = 0.056
18956 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.070	76 restraints
wR(F²) = 0.170	H-atom parameters constrained
S = 1.31	Δρ_max = 0.85 e Å⁻³
5964 reflections	Δρ_min = −0.72 e Å⁻³
358 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Cd1	0.64381 (8)	0.753688 (19)	0.52186 (3)	0.0473 (2)
Cl1	0.484 (3)	0.6172 (12)	0.3411 (19)	0.163 (3)	0.50
Cl2	0.3864 (15)	0.5394 (4)	0.4309 (8)	0.201 (4)	0.50
Cl3	0.7627 (15)	0.5707 (5)	0.4502 (9)	0.219 (4)	0.50
Cl1'	0.479 (3)	0.6169 (12)	0.3297 (19)	0.163 (3)	0.50
Cl2'	0.2584 (15)	0.5496 (5)	0.3957 (8)	0.201 (4)	0.50
Cl3'	0.6405 (16)	0.5623 (5)	0.4624 (9)	0.219 (4)	0.50
S1	0.6020 (3)	0.84105 (7)	0.57280 (13)	0.0553 (5)
S2	0.9794 (3)	0.80367 (8)	0.55465 (14)	0.0620 (6)
S3	0.3644 (3)	0.69545 (9)	0.55197 (13)	0.0648 (6)
S4	0.7601 (3)	0.68697 (8)	0.63055 (13)	0.0603 (6)
N1	0.9189 (8)	0.8918 (2)	0.6032 (5)	0.069 (2)
N2	0.4809 (7)	0.6337 (2)	0.6669 (4)	0.0562 (17)
N3	0.7617 (8)	0.7162 (2)	0.4173 (3)	0.0520 (16)
N4	0.4490 (8)	0.7698 (2)	0.3965 (3)	0.0485 (15)
C1	0.8430 (10)	0.8488 (3)	0.5790 (4)	0.0511 (19)
C2	1.1238 (10)	0.8984 (4)	0.6258 (9)	0.142 (6)
H2A	1.1532	0.9172	0.6738	0.170*
H2B	1.1876	0.8675	0.6337	0.170*
C3	1.179 (2)	0.9245 (6)	0.5578 (9)	0.190 (8)
H3A	1.3126	0.9306	0.5680	0.285*
H3B	1.1126	0.9546	0.5505	0.285*
H3C	1.1486	0.9053	0.5110	0.285*
C4	0.8064 (7)	0.93085 (18)	0.6236 (4)	0.066 (2)
C5	0.7457 (9)	0.9666 (2)	0.5687 (3)	0.082 (3)
H5	0.7698	0.9639	0.5173	0.098*
C6	0.6491 (8)	1.0065 (2)	0.5904 (5)	0.089 (3)
H6	0.6085	1.0304	0.5536	0.107*
C7	0.6131 (8)	1.0105 (2)	0.6671 (5)	0.096 (4)
H7	0.5484	1.0372	0.6816	0.115*
C8	0.6738 (10)	0.9748 (3)	0.7220 (4)	0.106 (4)
H8	0.6497	0.9775	0.7734	0.127*
C9	0.7704 (9)	0.9349 (2)	0.7003 (4)	0.092 (3)
H9	0.8110	0.9110	0.7371	0.110*
C10	0.5316 (9)	0.6685 (3)	0.6205 (4)	0.0444 (17)
C11	0.2868 (9)	0.6185 (3)	0.6667 (5)	0.074 (3)
H11A	0.2024	0.6449	0.6486	0.089*
H11B	0.2707	0.6105	0.7201	0.089*
C12	0.2348 (17)	0.5758 (3)	0.6147 (7)	0.109 (4)
H12A	0.1066	0.5668	0.6163	0.164*
H12B	0.3168	0.5493	0.6328	0.164*
H12C	0.2477	0.5837	0.5615	0.164*
C13	0.6215 (7)	0.61172 (18)	0.7254 (3)	0.0520 (19)
C14	0.6465 (8)	0.62834 (18)	0.8028 (3)	0.065 (2)
H14	0.5752	0.6541	0.8160	0.078*
C15	0.7781 (9)	0.6064 (2)	0.8604 (3)	0.084 (3)
H15	0.7948	0.6175	0.9121	0.101*
C16	0.8846 (8)	0.5679 (2)	0.8406 (4)	0.093 (3)
H16	0.9726	0.5532	0.8792	0.112*
C17	0.8596 (8)	0.5513 (2)	0.7633 (4)	0.090 (3)
H17	0.9309	0.5255	0.7501	0.108*
C18	0.7281 (9)	0.5732 (2)	0.7057 (3)	0.076 (3)
H18	0.7114	0.5621	0.6540	0.092*
C19	0.9258 (11)	0.6929 (3)	0.4302 (5)	0.071 (3)
H19	0.9829	0.6873	0.4821	0.085*
C20	1.0139 (13)	0.6769 (4)	0.3707 (6)	0.082 (3)
H20	1.1280	0.6605	0.3822	0.098*
C21	0.9331 (13)	0.6851 (3)	0.2945 (6)	0.073 (3)
H21	0.9920	0.6752	0.2530	0.088*
C22	0.7648 (13)	0.7082 (3)	0.2806 (5)	0.067 (2)
H22	0.7058	0.7136	0.2290	0.080*
C23	0.6803 (10)	0.7236 (3)	0.3425 (4)	0.0488 (18)
C24	0.4952 (10)	0.7492 (3)	0.3318 (4)	0.0512 (18)
C25	0.3768 (12)	0.7501 (3)	0.2588 (5)	0.064 (2)
H25	0.4117	0.7350	0.2151	0.077*
C26	0.2083 (14)	0.7738 (4)	0.2528 (6)	0.080 (3)
H26	0.1269	0.7751	0.2048	0.096*
C27	0.1606 (12)	0.7954 (4)	0.3178 (7)	0.081 (3)
H27	0.0460	0.8114	0.3149	0.098*
C28	0.2842 (11)	0.7932 (3)	0.3876 (5)	0.063 (2)
H28	0.2518	0.8089	0.4312	0.076*
C29	0.5297 (17)	0.5900 (6)	0.4329 (14)	0.117 (6)	0.50
H29	0.5059	0.6125	0.4741	0.141*	0.50
C29'	0.4379 (19)	0.5918 (6)	0.4173 (13)	0.117 (6)	0.50
H29'	0.4021	0.6168	0.4522	0.141*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0559 (3)	0.0480 (3)	0.0360 (3)	−0.0026 (3)	0.0020 (2)	−0.0005 (3)
Cl1	0.184 (4)	0.141 (3)	0.178 (6)	−0.006 (3)	0.071 (3)	−0.005 (4)
Cl2	0.221 (7)	0.174 (5)	0.217 (7)	−0.039 (6)	0.063 (6)	0.007 (5)
Cl3	0.225 (7)	0.212 (6)	0.208 (6)	0.018 (6)	0.000 (6)	−0.007 (5)
Cl1'	0.184 (4)	0.141 (3)	0.178 (6)	−0.006 (3)	0.071 (3)	−0.005 (4)
Cl2'	0.221 (7)	0.174 (5)	0.217 (7)	−0.039 (6)	0.063 (6)	0.007 (5)
Cl3'	0.225 (7)	0.212 (6)	0.208 (6)	0.018 (6)	0.000 (6)	−0.007 (5)
S1	0.0463 (10)	0.0549 (12)	0.0626 (13)	−0.0009 (9)	0.0029 (9)	−0.0126 (10)
S2	0.0562 (12)	0.0569 (12)	0.0749 (15)	0.0013 (10)	0.0168 (11)	−0.0120 (11)
S3	0.0468 (11)	0.0820 (15)	0.0588 (13)	−0.0022 (11)	−0.0107 (10)	0.0217 (11)
S4	0.0455 (10)	0.0728 (14)	0.0572 (13)	−0.0096 (10)	−0.0072 (9)	0.0204 (11)
N1	0.041 (4)	0.056 (4)	0.113 (6)	−0.005 (3)	0.017 (4)	−0.025 (4)
N2	0.044 (3)	0.064 (4)	0.056 (4)	−0.005 (3)	−0.002 (3)	0.013 (3)
N3	0.050 (4)	0.065 (4)	0.037 (4)	0.001 (3)	−0.003 (3)	−0.010 (3)
N4	0.049 (3)	0.055 (4)	0.039 (4)	0.002 (3)	0.001 (3)	0.004 (3)
C1	0.055 (4)	0.054 (5)	0.044 (4)	−0.004 (4)	0.006 (4)	−0.008 (4)
C2	0.138 (12)	0.066 (7)	0.254 (19)	−0.006 (7)	0.127 (13)	−0.033 (9)
C3	0.109 (11)	0.182 (18)	0.27 (2)	0.035 (12)	0.010 (14)	−0.054 (17)
C4	0.051 (5)	0.059 (5)	0.086 (7)	−0.016 (4)	0.004 (5)	−0.019 (5)
C5	0.066 (6)	0.079 (7)	0.095 (8)	0.006 (5)	−0.005 (5)	−0.028 (6)
C6	0.061 (6)	0.075 (7)	0.120 (10)	0.003 (5)	−0.017 (6)	−0.030 (6)
C7	0.073 (6)	0.061 (6)	0.154 (12)	−0.008 (5)	0.018 (7)	−0.039 (7)
C8	0.114 (9)	0.077 (8)	0.136 (11)	−0.005 (7)	0.050 (8)	−0.044 (8)
C9	0.101 (8)	0.059 (6)	0.123 (10)	−0.005 (6)	0.039 (7)	−0.008 (6)
C10	0.044 (4)	0.054 (4)	0.032 (4)	0.000 (3)	−0.002 (3)	0.000 (3)
C11	0.064 (5)	0.080 (6)	0.076 (7)	−0.003 (5)	0.006 (5)	0.014 (5)
C12	0.114 (9)	0.097 (8)	0.114 (10)	−0.028 (7)	0.012 (8)	−0.003 (7)
C13	0.055 (4)	0.046 (4)	0.057 (5)	−0.001 (4)	0.013 (4)	0.012 (4)
C14	0.082 (6)	0.052 (5)	0.058 (5)	0.003 (4)	−0.001 (5)	0.003 (4)
C15	0.098 (7)	0.085 (7)	0.060 (6)	−0.011 (6)	−0.013 (5)	0.012 (5)
C16	0.079 (7)	0.103 (8)	0.092 (8)	0.018 (6)	−0.004 (6)	0.038 (7)
C17	0.073 (6)	0.096 (8)	0.102 (8)	0.038 (6)	0.017 (6)	0.032 (7)
C18	0.088 (6)	0.087 (7)	0.058 (6)	0.022 (6)	0.023 (5)	0.010 (5)
C19	0.056 (5)	0.099 (7)	0.054 (5)	0.018 (5)	−0.005 (4)	−0.009 (5)
C20	0.058 (5)	0.094 (7)	0.091 (8)	0.021 (5)	0.005 (5)	−0.021 (6)
C21	0.070 (6)	0.085 (7)	0.066 (6)	−0.008 (5)	0.017 (5)	−0.026 (5)
C22	0.085 (6)	0.075 (6)	0.040 (5)	−0.006 (5)	0.008 (4)	−0.005 (4)
C23	0.053 (4)	0.052 (4)	0.039 (4)	−0.013 (4)	−0.001 (4)	−0.004 (3)
C24	0.057 (4)	0.048 (4)	0.047 (4)	−0.013 (4)	0.006 (4)	0.009 (4)
C25	0.067 (5)	0.068 (5)	0.050 (5)	−0.005 (5)	−0.013 (4)	0.007 (4)
C26	0.069 (6)	0.094 (7)	0.068 (7)	−0.010 (6)	−0.018 (5)	0.013 (6)
C27	0.046 (5)	0.084 (7)	0.108 (9)	0.008 (5)	−0.005 (5)	0.017 (6)
C28	0.051 (5)	0.061 (5)	0.077 (6)	0.005 (4)	0.010 (4)	0.012 (4)
C29	0.126 (11)	0.105 (8)	0.121 (9)	0.009 (8)	0.022 (9)	0.010 (7)
C29'	0.126 (11)	0.105 (8)	0.121 (9)	0.009 (8)	0.022 (9)	0.010 (7)

Geometric parameters (Å, º) top

Cd1—N3	2.355 (6)	C8—C9	1.3900
Cd1—N4	2.408 (6)	C8—H8	0.9300
Cd1—S1	2.612 (2)	C9—H9	0.9300
Cd1—S4	2.664 (2)	C11—C12	1.493 (5)
Cd1—S3	2.696 (2)	C11—H11A	0.9700
Cd1—S2	2.759 (2)	C11—H11B	0.9700
Cl1—C29	1.731 (9)	C12—H12A	0.9600
Cl2—C29	1.740 (9)	C12—H12B	0.9600
Cl3—C29	1.737 (9)	C12—H12C	0.9600
Cl1'—C29'	1.730 (9)	C13—C14	1.3900
Cl2'—C29'	1.736 (9)	C13—C18	1.3900
Cl3'—C29'	1.736 (9)	C14—C15	1.3900
S1—C1	1.731 (8)	C14—H14	0.9300
S2—C1	1.686 (8)	C15—C16	1.3900
S3—C10	1.709 (7)	C15—H15	0.9300
S4—C10	1.703 (7)	C16—C17	1.3900
N1—C1	1.350 (9)	C16—H16	0.9300
N1—C4	1.430 (7)	C17—C18	1.3900
N1—C2	1.471 (5)	C17—H17	0.9300
N2—C10	1.341 (9)	C18—H18	0.9300
N2—C13	1.438 (7)	C19—C20	1.363 (12)
N2—C11	1.458 (5)	C19—H19	0.9300
N3—C19	1.332 (10)	C20—C21	1.362 (13)
N3—C23	1.335 (9)	C20—H20	0.9300
N4—C28	1.338 (9)	C21—C22	1.354 (12)
N4—C24	1.341 (10)	C21—H21	0.9300
C2—C3	1.486 (5)	C22—C23	1.379 (11)
C2—H2A	0.9700	C22—H22	0.9300
C2—H2B	0.9700	C23—C24	1.493 (11)
C3—H3A	0.9600	C24—C25	1.394 (11)
C3—H3B	0.9600	C25—C26	1.367 (13)
C3—H3C	0.9600	C25—H25	0.9300
C4—C5	1.3900	C26—C27	1.362 (14)
C4—C9	1.3900	C26—H26	0.9300
C5—C6	1.3900	C27—C28	1.370 (12)
C5—H5	0.9300	C27—H27	0.9300
C6—C7	1.3900	C28—H28	0.9300
C6—H6	0.9300	C29—H29	0.9800
C7—C8	1.3900	C29'—H29'	0.9800
C7—H7	0.9300

N3—Cd1—N4	68.2 (2)	N2—C11—H11B	109.2
N3—Cd1—S1	137.94 (17)	C12—C11—H11B	109.2
N4—Cd1—S1	92.60 (15)	H11A—C11—H11B	107.9
N3—Cd1—S4	96.75 (16)	C11—C12—H12A	109.5
N4—Cd1—S4	145.52 (15)	C11—C12—H12B	109.5
S1—Cd1—S4	116.75 (7)	H12A—C12—H12B	109.5
N3—Cd1—S3	104.88 (16)	C11—C12—H12C	109.5
N4—Cd1—S3	86.69 (15)	H12A—C12—H12C	109.5
S1—Cd1—S3	111.16 (7)	H12B—C12—H12C	109.5
S4—Cd1—S3	66.76 (6)	C14—C13—C18	120.0
N3—Cd1—S2	87.94 (15)	C14—C13—N2	119.5 (5)
N4—Cd1—S2	116.60 (15)	C18—C13—N2	120.5 (5)
S1—Cd1—S2	67.08 (6)	C13—C14—C15	120.0
S4—Cd1—S2	92.56 (7)	C13—C14—H14	120.0
S3—Cd1—S2	156.49 (7)	C15—C14—H14	120.0
C1—S1—Cd1	88.0 (3)	C14—C15—C16	120.0
C1—S2—Cd1	84.2 (3)	C14—C15—H15	120.0
C10—S3—Cd1	86.2 (3)	C16—C15—H15	120.0
C10—S4—Cd1	87.3 (2)	C17—C16—C15	120.0
C1—N1—C4	122.0 (6)	C17—C16—H16	120.0
C1—N1—C2	121.8 (7)	C15—C16—H16	120.0
C4—N1—C2	115.1 (7)	C16—C17—C18	120.0
C10—N2—C13	119.5 (5)	C16—C17—H17	120.0
C10—N2—C11	124.2 (6)	C18—C17—H17	120.0
C13—N2—C11	116.1 (6)	C17—C18—C13	120.0
C19—N3—C23	118.0 (7)	C17—C18—H18	120.0
C19—N3—Cd1	120.6 (5)	C13—C18—H18	120.0
C23—N3—Cd1	120.7 (5)	N3—C19—C20	122.8 (8)
C28—N4—C24	116.8 (7)	N3—C19—H19	118.6
C28—N4—Cd1	124.3 (5)	C20—C19—H19	118.6
C24—N4—Cd1	118.4 (5)	C19—C20—C21	119.4 (8)
N1—C1—S2	120.8 (6)	C19—C20—H20	120.3
N1—C1—S1	118.5 (6)	C21—C20—H20	120.3
S2—C1—S1	120.7 (4)	C22—C21—C20	118.2 (9)
C3—C2—N1	104.0 (11)	C22—C21—H21	120.9
C3—C2—H2A	111.0	C20—C21—H21	120.9
N1—C2—H2A	111.0	C21—C22—C23	120.5 (8)
C3—C2—H2B	111.0	C21—C22—H22	119.8
N1—C2—H2B	111.0	C23—C22—H22	119.8
H2A—C2—H2B	109.0	N3—C23—C22	121.1 (7)
C2—C3—H3A	109.5	N3—C23—C24	115.5 (7)
C2—C3—H3B	109.5	C22—C23—C24	123.4 (7)
H3A—C3—H3B	109.5	N4—C24—C25	122.7 (8)
C2—C3—H3C	109.5	N4—C24—C23	116.1 (6)
H3A—C3—H3C	109.5	C25—C24—C23	121.2 (7)
H3B—C3—H3C	109.5	C26—C25—C24	118.5 (9)
C5—C4—C9	120.0	C26—C25—H25	120.8
C5—C4—N1	120.0 (6)	C24—C25—H25	120.8
C9—C4—N1	119.8 (6)	C27—C26—C25	119.4 (9)
C6—C5—C4	120.0	C27—C26—H26	120.3
C6—C5—H5	120.0	C25—C26—H26	120.3
C4—C5—H5	120.0	C26—C27—C28	118.9 (9)
C5—C6—C7	120.0	C26—C27—H27	120.5
C5—C6—H6	120.0	C28—C27—H27	120.5
C7—C6—H6	120.0	N4—C28—C27	123.7 (9)
C8—C7—C6	120.0	N4—C28—H28	118.2
C8—C7—H7	120.0	C27—C28—H28	118.2
C6—C7—H7	120.0	Cl1—C29—Cl3	108.6 (8)
C9—C8—C7	120.0	Cl1—C29—Cl2	108.2 (7)
C9—C8—H8	120.0	Cl3—C29—Cl2	107.8 (7)
C7—C8—H8	120.0	Cl1—C29—H29	110.7
C8—C9—C4	120.0	Cl3—C29—H29	110.7
C8—C9—H9	120.0	Cl2—C29—H29	110.7
C4—C9—H9	120.0	Cl1'—C29'—Cl2'	108.3 (7)
N2—C10—S4	120.7 (5)	Cl1'—C29'—Cl3'	109.0 (8)
N2—C10—S3	119.7 (5)	Cl2'—C29'—Cl3'	108.5 (7)
S4—C10—S3	119.6 (4)	Cl1'—C29'—H29'	110.3
N2—C11—C12	112.0 (7)	Cl2'—C29'—H29'	110.3
N2—C11—H11A	109.2	Cl3'—C29'—H29'	110.3
C12—C11—H11A	109.2

N3—Cd1—S1—C1	−57.8 (3)	N1—C4—C5—C6	−175.0 (5)
N4—Cd1—S1—C1	−117.5 (3)	C4—C5—C6—C7	0.0
S4—Cd1—S1—C1	81.3 (3)	C5—C6—C7—C8	0.0
S3—Cd1—S1—C1	155.1 (3)	C6—C7—C8—C9	0.0
S2—Cd1—S1—C1	0.4 (3)	C7—C8—C9—C4	0.0
N3—Cd1—S2—C1	144.9 (3)	C5—C4—C9—C8	0.0
N4—Cd1—S2—C1	80.6 (3)	N1—C4—C9—C8	175.0 (5)
S1—Cd1—S2—C1	−0.4 (3)	C13—N2—C10—S4	−0.1 (10)
S4—Cd1—S2—C1	−118.5 (3)	C11—N2—C10—S4	174.8 (6)
S3—Cd1—S2—C1	−91.0 (3)	C13—N2—C10—S3	−178.9 (5)
N3—Cd1—S3—C10	92.9 (3)	C11—N2—C10—S3	−4.0 (10)
N4—Cd1—S3—C10	159.3 (3)	Cd1—S4—C10—N2	−175.7 (6)
S1—Cd1—S3—C10	−109.2 (3)	Cd1—S4—C10—S3	3.1 (4)
S4—Cd1—S3—C10	1.9 (3)	Cd1—S3—C10—N2	175.7 (6)
S2—Cd1—S3—C10	−28.2 (3)	Cd1—S3—C10—S4	−3.1 (4)
N3—Cd1—S4—C10	−105.2 (3)	C10—N2—C11—C12	95.3 (10)
N4—Cd1—S4—C10	−44.4 (4)	C13—N2—C11—C12	−89.6 (9)
S1—Cd1—S4—C10	101.0 (3)	C10—N2—C13—C14	96.2 (7)
S3—Cd1—S4—C10	−1.9 (3)	C11—N2—C13—C14	−79.1 (7)
S2—Cd1—S4—C10	166.6 (3)	C10—N2—C13—C18	−85.7 (7)
N4—Cd1—N3—C19	174.9 (7)	C11—N2—C13—C18	98.9 (7)
S1—Cd1—N3—C19	106.6 (6)	C18—C13—C14—C15	0.0
S4—Cd1—N3—C19	−37.2 (6)	N2—C13—C14—C15	178.1 (5)
S3—Cd1—N3—C19	−104.9 (6)	C13—C14—C15—C16	0.0
S2—Cd1—N3—C19	55.1 (6)	C14—C15—C16—C17	0.0
N4—Cd1—N3—C23	4.6 (5)	C15—C16—C17—C18	0.0
S1—Cd1—N3—C23	−63.6 (6)	C16—C17—C18—C13	0.0
S4—Cd1—N3—C23	152.5 (5)	C14—C13—C18—C17	0.0
S3—Cd1—N3—C23	84.8 (5)	N2—C13—C18—C17	−178.0 (5)
S2—Cd1—N3—C23	−115.2 (5)	C23—N3—C19—C20	0.7 (13)
N3—Cd1—N4—C28	174.0 (6)	Cd1—N3—C19—C20	−169.8 (7)
S1—Cd1—N4—C28	−44.5 (6)	N3—C19—C20—C21	0.5 (15)
S4—Cd1—N4—C28	105.0 (6)	C19—C20—C21—C22	−1.4 (15)
S3—Cd1—N4—C28	66.5 (6)	C20—C21—C22—C23	1.2 (14)
S2—Cd1—N4—C28	−110.1 (6)	C19—N3—C23—C22	−0.9 (11)
N3—Cd1—N4—C24	2.5 (5)	Cd1—N3—C23—C22	169.6 (6)
S1—Cd1—N4—C24	144.0 (5)	C19—N3—C23—C24	179.0 (7)
S4—Cd1—N4—C24	−66.4 (6)	Cd1—N3—C23—C24	−10.4 (8)
S3—Cd1—N4—C24	−104.9 (5)	C21—C22—C23—N3	0.0 (13)
S2—Cd1—N4—C24	78.4 (5)	C21—C22—C23—C24	180.0 (7)
C4—N1—C1—S2	179.5 (6)	C28—N4—C24—C25	−2.2 (11)
C2—N1—C1—S2	−13.4 (13)	Cd1—N4—C24—C25	169.9 (6)
C4—N1—C1—S1	0.0 (11)	C28—N4—C24—C23	179.4 (6)
C2—N1—C1—S1	167.1 (8)	Cd1—N4—C24—C23	−8.5 (8)
Cd1—S2—C1—N1	−178.8 (7)	N3—C23—C24—N4	12.3 (9)
Cd1—S2—C1—S1	0.7 (4)	C22—C23—C24—N4	−167.7 (7)
Cd1—S1—C1—N1	178.8 (7)	N3—C23—C24—C25	−166.1 (7)
Cd1—S1—C1—S2	−0.7 (5)	C22—C23—C24—C25	13.8 (11)
C1—N1—C2—C3	104.8 (12)	N4—C24—C25—C26	1.1 (12)
C4—N1—C2—C3	−87.3 (12)	C23—C24—C25—C26	179.4 (8)
C1—N1—C4—C5	−97.3 (8)	C24—C25—C26—C27	−0.3 (14)
C2—N1—C4—C5	94.8 (9)	C25—C26—C27—C28	0.6 (15)
C1—N1—C4—C9	87.7 (8)	C24—N4—C28—C27	2.5 (12)
C2—N1—C4—C9	−80.2 (9)	Cd1—N4—C28—C27	−169.0 (7)
C9—C4—C5—C6	0.0	C26—C27—C28—N4	−1.8 (14)

Experimental details

Crystal data
Chemical formula	[Cd(C₉H₁₀NS₂)₂(C₁₀H₈N₂)]·CHCl₃
M_r	780.55
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	7.1911 (6), 27.752 (3), 17.1907 (16)
β (°)	99.620 (5)
V (Å³)	3382.5 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.16
Crystal size (mm)	0.23 × 0.06 × 0.01

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.777, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	18956, 5964, 4307
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.070, 0.170, 1.31
No. of reflections	5964
No. of parameters	358
No. of restraints	76
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.85, −0.72

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

We thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08–27-111 and 06–01-02-SF0539) and the University of Malaya for supporting this study.

References

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