Tetra­kis(2-amino­thia­zole-κN3)dichloridocadmium(II)

Kim, C.-H.; Kim, I.H.

doi:10.1107/S1600536809051770

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page m13

doi:10.1107/S1600536809051770

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Tetrakis(2-aminothiazole-κN³)dichloridocadmium(II)

Chong-Hyeak Kim ^a and Inn Hoe Kim ^b ^*

^aCenter for Chemical Analysis, Korea Research Institute of Chemical Technology, PO Box 107, Yuseong, Daejeon 305-600, Republic of Korea, and ^bDepartment of Chemistry, Konyang University, Nonsan 320-711, Republic of Korea
^*Correspondence e-mail: ihkim@konyang.ac.kr

(Received 26 November 2009; accepted 1 December 2009; online 4 December 2009)

In the title complex, [CdCl₂(C₃H₄N₂S)₄],the Cd^II atom has an trans-Cl₂N₄ octahedral coordination geometry defined by four N atoms derived from the four 2-aminothiazole ligands and two Cl atoms. The amino groups participate in intra- and intermolecular N—H⋯N and N—H⋯Cl hydrogen bonding that stabilizes both the molecular and crystal structures.

Related literature

For the coordination properties of heterocycles, see: Raper (1994 ); Karlin & Zubieta (1983 ). For the structures of related aminothiazole complexes, see: Batı et al. (2006 ); Davarski et al. (1996 ); Macíček & Davarski (1993 ); Maniukiewicz (2004 ); Raper et al. (1981 ); Suh et al. (2005 , 2007 , 2009 ).

Experimental

Crystal data

[CdCl₂(C₃H₄N₂S)₄]
M_r = 583.87
Monoclinic, P 2₁ /c
a = 8.6056 (1) Å
b = 15.2838 (2) Å
c = 16.2097 (2) Å
β = 103.605 (1)°
V = 2072.18 (4) Å³
Z = 4
Mo Kα radiation
μ = 1.73 mm⁻¹
T = 296 K
0.40 × 0.19 × 0.08 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.544, T_max = 0.870
21163 measured reflections
5159 independent reflections
4532 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.052
S = 1.05
5159 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N16—H16A⋯N23	0.86	2.63	3.277 (2)	133
N16—H16A⋯Cl1	0.86	2.81	3.3903 (19)	126
N16—H16B⋯Cl2ⁱ	0.86	2.52	3.2941 (18)	151
N26—H26A⋯Cl2	0.86	2.41	3.1722 (17)	149
N26—H26B⋯Cl1ⁱⁱ	0.86	2.51	3.3300 (16)	161
N36—H36A⋯N43	0.86	2.61	3.324 (2)	142
N36—H36B⋯Cl1ⁱⁱⁱ	0.86	2.63	3.3810 (18)	147
N46—H46A⋯Cl1	0.86	2.44	3.2135 (18)	150
N46—H46B⋯N36^iv	0.86	2.56	3.417 (2)	177
Symmetry codes: (i) x+1, y, z; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) x-1, y, z; (iv) -x, -y, -z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809051770/tk2590sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809051770/tk2590Isup2.hkl

checkCIF report

Comment top

Some heterocyclic organic compounds have biologically useful properties, having anti-tumour, anti-fungal, and anti-infection activities. Amongst these, aminothiazoles are an important type of N,S-containing heterocycle (Raper, 1994). The N and S atoms play a key role in the coordination of metals at the active sites of various metallobiomelecules (Karlin & Zubieta, 1983). The crystal structures of aminothiazole complexes have attracted recent interest (Suh et al., 2005, 2007, 2009; Batı et al., 2006; Davarski et al., 1996; Macíček & Davarski, 1993; Maniukiewicz, 2004; Raper et al., 1981). Herein, we report the synthesis and crystal structure of the title complex, (I).

As shown in Fig. 1, the complex (I) comprises discrete Cd(C₃H₄N₂S)₄Cl₂ molecules. The octahedral Cd^II coordination environment is defined by four N atoms derived from four neutral monodentate 2-aminothiazole ligands and two Cl atoms [Cd—Cl = 2.6294 (5) and 2.6560 (4) Å, and Cd—N = 2.3569 (14)-2.4432 (14) Å]. The Cl atoms occupy trans positions. The amino groups participate in intra- and inter-molecular N—H···N and N—H···Cl hydrogen bonds (Table 1). In the crystal structure molecules are interconnected by these interactions into a three-dimensional hydrogen bond network (Fig. 2).

Related literature top

For the coordination properties of heterocycles, see: Raper (1994); Karlin & Zubieta (1983). For the structures of related aminothiazole complexes, see: Batı et al. (2006); Davarski et al. (1996); Macíček & Davarski (1993); Maniukiewicz (2004); Raper et al. (1981); Suh et al. (2005, 2007, 2009).

Experimental top

A water–ethanol (1:1) solution (40 ml) of 2-aminothiazole (5 mmol) was added dropwise to a water–ethanol (1:1) solution (40 ml) of CdCl₂.2.5H₂O (2 mmol) with stirring. The small amount of precipitates formed from the mixed solution were filtered off. The filtered solution was allowed to stand at room temperature. After several days, yellow blocks were obtained. Analysis found: C 24.95, H 2.74, N 19.11, S 21.72, Cd 19.30%; C₁₂H₁₆CdCl₂N₈S₄ requires: C 24.68, H 2.76, N 19.20, S 21.96, Cl 12.14, Cd 19.25%.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view of the unit cell contents of (I). The C–H atoms have been omitted for reasons of clarity (dashed lines).

Tetrakis(2-aminothiazole-κN³)dichloridocadmium(II) top

Crystal data top

[CdCl₂(C₃H₄N₂S)₄]	F(000) = 1160
M_r = 583.87	D_x = 1.872 Mg m⁻³ D_m = 1.87 Mg m⁻³ D_m measured by flotation method
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5290 reflections
a = 8.6056 (1) Å	θ = 2.7–28.3°
b = 15.2838 (2) Å	µ = 1.73 mm⁻¹
c = 16.2097 (2) Å	T = 296 K
β = 103.605 (1)°	Block, yellow
V = 2072.18 (4) Å³	0.40 × 0.19 × 0.08 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	5159 independent reflections
Radiation source: fine-focus sealed tube	4532 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.544, T_max = 0.87	k = −20→20
21163 measured reflections	l = −20→21

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)] = 0.021	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.052	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0234P)² + 0.6132P] where P = (F_o² + 2F_c²)/3
5159 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[CdCl₂(C₃H₄N₂S)₄]	V = 2072.18 (4) Å³
M_r = 583.87	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.6056 (1) Å	µ = 1.73 mm⁻¹
b = 15.2838 (2) Å	T = 296 K
c = 16.2097 (2) Å	0.40 × 0.19 × 0.08 mm
β = 103.605 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	5159 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	4532 reflections with I > 2σ(I)
T_min = 0.544, T_max = 0.87	R_int = 0.020
21163 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	0 restraints
wR(F²) = 0.052	H-atom parameters constrained
S = 1.05	Δρ_max = 0.36 e Å⁻³
5159 reflections	Δρ_min = −0.30 e Å⁻³
244 parameters

Special details top

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
Cd	0.237289 (14)	0.127887 (8)	0.242806 (7)	0.02555 (5)
Cl1	0.41984 (5)	0.15665 (3)	0.13431 (3)	0.03443 (10)
Cl2	0.05073 (6)	0.10433 (3)	0.34816 (3)	0.03723 (11)
S11	0.72017 (6)	−0.00335 (3)	0.42080 (3)	0.04305 (13)
C12	0.6028 (2)	0.07360 (12)	0.35499 (11)	0.0312 (4)
N13	0.44963 (17)	0.05509 (9)	0.33585 (9)	0.0304 (3)
C14	0.4223 (2)	−0.02238 (12)	0.37465 (12)	0.0369 (4)
H14A	0.3200	−0.0453	0.3682	0.044*
C15	0.5505 (3)	−0.06232 (13)	0.42170 (13)	0.0432 (5)
H15	0.5485	−0.1146	0.4508	0.052*
N16	0.6685 (2)	0.14549 (12)	0.33020 (12)	0.0482 (5)
H16A	0.6089	0.1839	0.2992	0.058*
H16B	0.7702	0.1532	0.3453	0.058*
S21	0.44426 (7)	0.38898 (3)	0.41822 (3)	0.04409 (13)
C22	0.3558 (2)	0.28774 (11)	0.39147 (11)	0.0292 (4)
N23	0.34496 (18)	0.26409 (9)	0.31227 (9)	0.0295 (3)
C24	0.4114 (2)	0.32847 (12)	0.27081 (12)	0.0367 (4)
H24A	0.4153	0.3226	0.2142	0.044*
C25	0.4692 (3)	0.39916 (14)	0.31605 (13)	0.0440 (5)
H25	0.5160	0.4468	0.2956	0.053*
N26	0.3052 (2)	0.23949 (10)	0.44936 (10)	0.0400 (4)
H26A	0.2620	0.1892	0.4356	0.048*
H26B	0.3159	0.2589	0.5002	0.048*
S31	−0.24063 (6)	0.26745 (4)	0.06541 (4)	0.04824 (14)
C32	−0.1262 (2)	0.18601 (12)	0.12468 (11)	0.0327 (4)
N33	0.02729 (18)	0.20338 (10)	0.14653 (9)	0.0311 (3)
C34	0.0573 (2)	0.28381 (12)	0.11430 (12)	0.0384 (4)
H34A	0.1601	0.3066	0.1230	0.046*
C35	−0.0703 (3)	0.32678 (14)	0.06998 (13)	0.0467 (5)
H35	−0.0670	0.3814	0.0451	0.056*
N36	−0.1933 (2)	0.10964 (11)	0.14150 (12)	0.0458 (4)
H36A	−0.1340	0.0685	0.1683	0.055*
H36B	−0.2950	0.1024	0.1254	0.055*
S41	0.07311 (8)	−0.15017 (3)	0.08737 (4)	0.05010 (14)
C42	0.1437 (2)	−0.04377 (12)	0.10337 (11)	0.0319 (4)
N43	0.13773 (18)	−0.01062 (9)	0.17752 (9)	0.0309 (3)
C44	0.0725 (2)	−0.07152 (12)	0.22319 (12)	0.0385 (4)
H44A	0.0581	−0.0591	0.2771	0.046*
C45	0.0316 (3)	−0.14861 (13)	0.18614 (13)	0.0446 (5)
H45	−0.0129	−0.1948	0.2101	0.054*
N46	0.1983 (2)	−0.00158 (11)	0.04363 (10)	0.0455 (4)
H46A	0.2329	0.0512	0.0524	0.055*
H46B	0.1987	−0.0272	−0.0035	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd	0.02192 (7)	0.02708 (7)	0.02791 (7)	0.00039 (5)	0.00638 (5)	0.00172 (5)
Cl1	0.0292 (2)	0.0456 (3)	0.0302 (2)	−0.00291 (19)	0.01048 (17)	0.00135 (18)
Cl2	0.0292 (2)	0.0449 (3)	0.0411 (2)	−0.00374 (19)	0.01530 (19)	−0.0022 (2)
S11	0.0319 (3)	0.0432 (3)	0.0476 (3)	0.0073 (2)	−0.0034 (2)	0.0046 (2)
C12	0.0268 (9)	0.0340 (9)	0.0320 (9)	0.0029 (7)	0.0052 (7)	−0.0023 (7)
N13	0.0257 (7)	0.0313 (8)	0.0331 (8)	0.0016 (6)	0.0047 (6)	0.0035 (6)
C14	0.0342 (10)	0.0359 (10)	0.0395 (10)	−0.0050 (8)	0.0063 (8)	0.0053 (8)
C15	0.0451 (12)	0.0348 (10)	0.0462 (11)	0.0008 (9)	0.0033 (9)	0.0097 (9)
N16	0.0252 (9)	0.0486 (10)	0.0682 (12)	−0.0030 (7)	0.0054 (8)	0.0154 (9)
S21	0.0559 (3)	0.0367 (3)	0.0391 (3)	−0.0151 (2)	0.0100 (2)	−0.0074 (2)
C22	0.0275 (9)	0.0268 (8)	0.0313 (9)	0.0013 (7)	0.0028 (7)	−0.0005 (7)
N23	0.0310 (8)	0.0275 (7)	0.0295 (7)	−0.0006 (6)	0.0063 (6)	0.0009 (6)
C24	0.0377 (10)	0.0407 (11)	0.0310 (9)	−0.0061 (8)	0.0066 (8)	0.0035 (8)
C25	0.0495 (13)	0.0413 (11)	0.0411 (11)	−0.0136 (9)	0.0103 (9)	0.0042 (9)
N26	0.0550 (11)	0.0371 (9)	0.0281 (8)	−0.0106 (8)	0.0101 (7)	−0.0006 (7)
S31	0.0343 (3)	0.0509 (3)	0.0531 (3)	0.0143 (2)	−0.0025 (2)	0.0033 (2)
C32	0.0275 (9)	0.0375 (10)	0.0317 (9)	0.0055 (8)	0.0045 (7)	−0.0035 (8)
N33	0.0261 (8)	0.0324 (8)	0.0330 (8)	0.0028 (6)	0.0036 (6)	0.0023 (6)
C34	0.0361 (11)	0.0364 (10)	0.0414 (10)	−0.0012 (8)	0.0067 (8)	0.0057 (8)
C35	0.0504 (13)	0.0384 (11)	0.0483 (12)	0.0074 (10)	0.0056 (10)	0.0097 (9)
N36	0.0262 (9)	0.0461 (10)	0.0622 (11)	−0.0022 (7)	0.0045 (8)	0.0047 (8)
S41	0.0633 (4)	0.0360 (3)	0.0516 (3)	−0.0144 (3)	0.0148 (3)	−0.0128 (2)
C42	0.0263 (9)	0.0302 (9)	0.0369 (10)	−0.0011 (7)	0.0029 (7)	−0.0014 (7)
N43	0.0302 (8)	0.0266 (7)	0.0352 (8)	−0.0018 (6)	0.0064 (6)	−0.0013 (6)
C44	0.0405 (11)	0.0370 (10)	0.0380 (10)	−0.0067 (8)	0.0096 (8)	0.0005 (8)
C45	0.0468 (13)	0.0361 (10)	0.0497 (12)	−0.0121 (9)	0.0086 (10)	0.0030 (9)
N46	0.0569 (12)	0.0439 (10)	0.0374 (9)	−0.0117 (8)	0.0147 (8)	−0.0049 (7)

Geometric parameters (Å, º) top

Cd—N13	2.3569 (14)	C25—H25	0.9300
Cd—N33	2.3886 (14)	N26—H26A	0.8600
Cd—N43	2.4308 (14)	N26—H26B	0.8600
Cd—N23	2.4432 (14)	S31—C35	1.711 (2)
Cd—Cl2	2.6294 (5)	S31—C32	1.7310 (19)
Cd—Cl1	2.6560 (4)	C32—N33	1.312 (2)
S11—C15	1.719 (2)	C32—N36	1.358 (2)
S11—C12	1.7420 (18)	N33—C34	1.384 (2)
C12—N13	1.312 (2)	C34—C35	1.335 (3)
C12—N16	1.340 (2)	C34—H34A	0.9300
N13—C14	1.387 (2)	C35—H35	0.9300
C14—C15	1.332 (3)	N36—H36A	0.8600
C14—H14A	0.9300	N36—H36B	0.8600
C15—H15	0.9300	S41—C45	1.721 (2)
N16—H16A	0.8600	S41—C42	1.7339 (18)
N16—H16B	0.8600	C42—N43	1.316 (2)
S21—C25	1.726 (2)	C42—N46	1.337 (2)
S21—C22	1.7341 (18)	N43—C44	1.387 (2)
C22—N23	1.316 (2)	C44—C45	1.332 (3)
C22—N26	1.344 (2)	C44—H44A	0.9300
N23—C24	1.388 (2)	C45—H45	0.9300
C24—C25	1.335 (3)	N46—H46A	0.8600
C24—H24A	0.9300	N46—H46B	0.8600

N13—Cd—N33	178.41 (5)	N23—C24—H24A	121.6
N13—Cd—N43	90.48 (5)	C24—C25—S21	109.85 (15)
N33—Cd—N43	90.07 (5)	C24—C25—H25	125.1
N13—Cd—N23	87.39 (5)	S21—C25—H25	125.1
N33—Cd—N23	92.07 (5)	C22—N26—H26A	120.0
N43—Cd—N23	177.85 (5)	C22—N26—H26B	120.0
N13—Cd—Cl2	91.13 (4)	H26A—N26—H26B	120.0
N33—Cd—Cl2	90.39 (4)	C35—S31—C32	89.29 (10)
N43—Cd—Cl2	87.53 (4)	N33—C32—N36	124.62 (17)
N23—Cd—Cl2	92.33 (4)	N33—C32—S31	114.17 (14)
N13—Cd—Cl1	90.66 (4)	N36—C32—S31	121.10 (14)
N33—Cd—Cl1	87.82 (4)	C32—N33—C34	110.08 (15)
N43—Cd—Cl1	93.36 (4)	C32—N33—Cd	129.62 (12)
N23—Cd—Cl1	86.84 (4)	C34—N33—Cd	119.74 (12)
Cl2—Cd—Cl1	177.991 (15)	C35—C34—N33	115.94 (19)
C15—S11—C12	89.30 (9)	C35—C34—H34A	122.0
N13—C12—N16	125.25 (17)	N33—C34—H34A	122.0
N13—C12—S11	113.89 (14)	C34—C35—S31	110.51 (16)
N16—C12—S11	120.83 (14)	C34—C35—H35	124.7
C12—N13—C14	110.17 (15)	S31—C35—H35	124.7
C12—N13—Cd	129.36 (12)	C32—N36—H36A	120.0
C14—N13—Cd	120.32 (12)	C32—N36—H36B	120.0
C15—C14—N13	116.44 (18)	H36A—N36—H36B	120.0
C15—C14—H14A	121.8	C45—S41—C42	89.42 (9)
N13—C14—H14A	121.8	N43—C42—N46	124.85 (17)
C14—C15—S11	110.20 (15)	N43—C42—S41	114.21 (14)
C14—C15—H15	124.9	N46—C42—S41	120.94 (14)
S11—C15—H15	124.9	C42—N43—C44	109.66 (15)
C12—N16—H16A	120.0	C42—N43—Cd	130.33 (12)
C12—N16—H16B	120.0	C44—N43—Cd	119.83 (11)
H16A—N16—H16B	120.0	C45—C44—N43	116.75 (18)
C25—S21—C22	89.25 (9)	C45—C44—H44A	121.6
N23—C22—N26	124.78 (16)	N43—C44—H44A	121.6
N23—C22—S21	114.54 (13)	C44—C45—S41	109.95 (15)
N26—C22—S21	120.69 (13)	C44—C45—H45	125.0
C22—N23—C24	109.57 (15)	S41—C45—H45	125.0
C22—N23—Cd	128.01 (11)	C42—N46—H46A	120.0
C24—N23—Cd	122.38 (11)	C42—N46—H46B	120.0
C25—C24—N23	116.79 (17)	H46A—N46—H46B	120.0
C25—C24—H24A	121.6

C15—S11—C12—N13	−0.25 (15)	C35—S31—C32—N33	0.69 (15)
C15—S11—C12—N16	177.77 (17)	C35—S31—C32—N36	−175.75 (17)
N16—C12—N13—C14	−177.55 (19)	N36—C32—N33—C34	175.40 (18)
S11—C12—N13—C14	0.36 (19)	S31—C32—N33—C34	−0.9 (2)
N16—C12—N13—Cd	7.0 (3)	N36—C32—N33—Cd	−13.3 (3)
S11—C12—N13—Cd	−175.09 (8)	S31—C32—N33—Cd	170.40 (8)
N43—Cd—N13—C12	131.98 (16)	N43—Cd—N33—C32	47.14 (16)
N23—Cd—N13—C12	−48.20 (15)	N23—Cd—N33—C32	−132.74 (16)
Cl2—Cd—N13—C12	−140.48 (15)	Cl2—Cd—N33—C32	−40.39 (15)
Cl1—Cd—N13—C12	38.61 (15)	Cl1—Cd—N33—C32	140.51 (15)
N43—Cd—N13—C14	−43.08 (13)	N43—Cd—N33—C34	−142.28 (14)
N23—Cd—N13—C14	136.74 (13)	N23—Cd—N33—C34	37.84 (14)
Cl2—Cd—N13—C14	44.46 (13)	Cl2—Cd—N33—C34	130.19 (13)
Cl1—Cd—N13—C14	−136.45 (13)	Cl1—Cd—N33—C34	−48.91 (13)
C12—N13—C14—C15	−0.3 (2)	C32—N33—C34—C35	0.7 (2)
Cd—N13—C14—C15	175.60 (14)	Cd—N33—C34—C35	−171.58 (14)
N13—C14—C15—S11	0.1 (2)	N33—C34—C35—S31	−0.2 (2)
C12—S11—C15—C14	0.05 (17)	C32—S31—C35—C34	−0.27 (17)
C25—S21—C22—N23	−0.46 (15)	C45—S41—C42—N43	0.69 (15)
C25—S21—C22—N26	179.14 (17)	C45—S41—C42—N46	−179.30 (17)
N26—C22—N23—C24	−178.86 (18)	N46—C42—N43—C44	179.12 (18)
S21—C22—N23—C24	0.72 (19)	S41—C42—N43—C44	−0.87 (19)
N26—C22—N23—Cd	−1.1 (3)	N46—C42—N43—Cd	−5.8 (3)
S21—C22—N23—Cd	178.50 (8)	S41—C42—N43—Cd	174.18 (8)
N13—Cd—N23—C22	−64.98 (15)	N13—Cd—N43—C42	−105.72 (16)
N33—Cd—N23—C22	116.52 (15)	N33—Cd—N43—C42	72.79 (16)
Cl2—Cd—N23—C22	26.04 (15)	Cl2—Cd—N43—C42	163.17 (16)
Cl1—Cd—N23—C22	−155.79 (15)	Cl1—Cd—N43—C42	−15.03 (16)
N13—Cd—N23—C24	112.54 (14)	N13—Cd—N43—C44	68.91 (14)
N33—Cd—N23—C24	−65.97 (14)	N33—Cd—N43—C44	−112.58 (14)
Cl2—Cd—N23—C24	−156.44 (13)	Cl2—Cd—N43—C44	−22.20 (13)
Cl1—Cd—N23—C24	21.73 (13)	Cl1—Cd—N43—C44	159.60 (13)
C22—N23—C24—C25	−0.7 (2)	C42—N43—C44—C45	0.7 (2)
Cd—N23—C24—C25	−178.63 (15)	Cd—N43—C44—C45	−174.98 (15)
N23—C24—C25—S21	0.4 (2)	N43—C44—C45—S41	−0.2 (2)
C22—S21—C25—C24	0.04 (17)	C42—S41—C45—C44	−0.28 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N16—H16A···N23	0.86	2.63	3.277 (2)	133
N16—H16A···Cl1	0.86	2.81	3.3903 (19)	126
N16—H16B···Cl2ⁱ	0.86	2.52	3.2941 (18)	151
N26—H26A···Cl2	0.86	2.41	3.1722 (17)	149
N26—H26B···Cl1ⁱⁱ	0.86	2.51	3.3300 (16)	161
N36—H36A···N43	0.86	2.61	3.324 (2)	142
N36—H36B···Cl1ⁱⁱⁱ	0.86	2.63	3.3810 (18)	147
N46—H46A···Cl1	0.86	2.44	3.2135 (18)	150
N46—H46B···N36^iv	0.86	2.56	3.417 (2)	177

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

Experimental details

Crystal data
Chemical formula	[CdCl₂(C₃H₄N₂S)₄]
M_r	583.87
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.6056 (1), 15.2838 (2), 16.2097 (2)
β (°)	103.605 (1)
V (Å³)	2072.18 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.73
Crystal size (mm)	0.40 × 0.19 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.544, 0.87
No. of measured, independent and observed [I > 2σ(I)] reflections	21163, 5159, 4532
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.052, 1.05
No. of reflections	5159
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.30

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N16—H16A···N23	0.86	2.63	3.277 (2)	132.7
N16—H16A···Cl1	0.86	2.81	3.3903 (19)	125.9
N16—H16B···Cl2ⁱ	0.86	2.52	3.2941 (18)	150.8
N26—H26A···Cl2	0.86	2.41	3.1722 (17)	148.8
N26—H26B···Cl1ⁱⁱ	0.86	2.51	3.3300 (16)	160.9
N36—H36A···N43	0.86	2.61	3.324 (2)	141.8
N36—H36B···Cl1ⁱⁱⁱ	0.86	2.63	3.3810 (18)	147.2
N46—H46A···Cl1	0.86	2.44	3.2135 (18)	150.3
N46—H46B···N36^iv	0.86	2.56	3.417 (2)	177.3

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

References

Batı, H., Yüksektepe, Ç., Çalı˛skan, N. & Büyükgüngör, O. (2006). Acta Cryst. E62, m2313–m2315. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Davarski, K., Macicek, J. & Konovalov, L. (1996). J. Coord. Chem. 38, 123–134. CrossRef CAS Web of Science Google Scholar
Karlin, K. D. & Zubieta, J. (1983). Biological and Inorganic Copper Chemistry. New York: Adenine Press. Google Scholar
Macíček, J. & Davarski, K. (1993). Acta Cryst. C49, 592–593. CSD CrossRef Web of Science IUCr Journals Google Scholar
Maniukiewicz, W. (2004). Acta Cryst. E60, m340–m341. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Raper, E. S. (1994). Coord. Chem. Rev. 129, 91–151. CrossRef CAS Web of Science Google Scholar
Raper, E. S., Oughtred, R. E., Nowell, I. W. & March, L. A. (1981). Acta Cryst. B37, 928–930. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suh, S. W., Kim, I. H. & Kim, C. H. (2005). Anal. Sci. Technol. 18, 386–390. Google Scholar
Suh, S. W., Kim, C.-H. & Kim, I. H. (2007). Acta Cryst. E63, m2177. Web of Science CSD CrossRef IUCr Journals Google Scholar
Suh, S. W., Kim, C.-H. & Kim, I. H. (2009). Acta Cryst. E65, m1054. Web of Science CSD CrossRef IUCr Journals Google Scholar

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