cis-Bis[4-amino-N-(pyrimidin-2-yl)benzene­sulfonamido-κ2N,N′]bis­(dimethyl sulfoxide-κO)cadmium

Hossain, G.M.G.

doi:10.1107/S1600536811010816

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m505-m506

doi:10.1107/S1600536811010816

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cis-Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamido-κ²N,N′]bis(dimethyl sulfoxide-κO)cadmium

G. M. Golzar Hossain ^a ^*

^aDepartment of Chemistry, University of Dhaka, Dhaka 1000, Bangladesh
^*Correspondence e-mail: acsbd@yahoo.com

(Received 14 February 2011; accepted 23 March 2011; online 26 March 2011)

The complete molecule of the title compound, [Cd(C₁₀H₉N₄O₂S)₂(C₂H₆OS)₂], is completed by the application of a twofold rotation axis. The Cd^II atom is six coordinated by two bidentate sulfadiazinate anions and two dimethylsulfoxide molecules. The resulting N₄O₂ donor set displays a distorted trigonal–prismatic coordination geometry. The S atom and methyl groups of dimethylsulfoxide are disordered over two sets of sites, with site occupancies of 0.715 (4) and 0.285 (4). The crystal structure features intermolecular N—H⋯N and N—H⋯O hydrogen bonds that lead to the formation of layers in the ab plane.

Related literature

For related structures, see: Heren et al. (2006 ); Hossain & Amoroso (2007 ). For background to hydrogen bonds formed by sulfadiazinate anions, see: Paşaoğlu et al. (2008 ).

Experimental

Crystal data

[Cd(C₁₀H₉N₄O₂S)₂(C₂H₆OS)₂]
M_r = 767.20
Orthorhombic, P b c n
a = 16.9168 (5) Å
b = 15.2448 (3) Å
c = 11.8402 (3) Å
V = 3053.51 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.04 mm⁻¹
T = 150 K
0.22 × 0.20 × 0.18 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (Blessing, 1995 ) T_min = 0.803, T_max = 0.835
21431 measured reflections
3503 independent reflections
2545 reflections with I > 2σ(I)
R_int = 0.088

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.102
S = 1.09
3503 reflections
235 parameters
30 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.78 e Å⁻³

Table 1
Selected bond lengths (Å)

Cd1—O1	2.268 (3)
Cd1—N11	2.305 (3)
Cd1—N12	2.452 (3)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N14—H14A⋯N13ⁱ	0.94 (3)	2.30 (3)	3.168 (5)	152 (4)
N14—H14B⋯O11ⁱⁱ	0.95 (3)	2.02 (3)	2.967 (5)	173 (4)
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Hooft, 1998 ); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811010816/tk2721sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811010816/tk2721Isup2.hkl

checkCIF report

Comment top

In an attempt to prepare a complex of sulfadiazine with the cadmium(II) ion in methanol by the reaction of a cadmium salt and sulfadiazine followed by crystallization from dimethylsulfoxide, the compound isolated was shown by crystallography to have the formula [Cd(C₁₀H₉N₄O₂S)₂](DMSO)₂.

The six coordinate cadmium complex is trigonal prismatic, Fig. 1. The C18–N14 bond distance of 1.366 (5) Å and the C15–S11–N11–C11 torsion angle of 66.1 (3) ° are comparable to those observed in related structures (Heren et al., 2006; Hossain & Amoroso, 2007). The Cd—O bond distance is shorter than the Cd—N bonds (Table 1). The dihedral angle between the aromatic rings of the anion of 88.65 (12) ° and this is greater than value of 71.10 (14) ° in the sulfadiazinate anion (Hossain & Amoroso, 2007). This is because in the latter the molecule is not bonded to a metal ion. The packing of (I) (Fig. 2) is stabilized by intermolecular N—H···N and N—H···O hydrogen bonds (Table 2) occurring between the anions in accord with a literature precedent (Paşaoğlu, et al., 2008). This hydrogen bonding leads to layers in the ab plane, Fig. 2.

Related literature top

For related structures, see: Heren et al. (2006); Hossain & Amoroso (2007). For background to hydrogen bonds formed by sulfadiazinate anions, see: Paşaoğlu et al. (2008).

Experimental top

The sodium salt of sulfadiazine (5.446 g, 2 mmol) was dissolved in hot methanol (50 ml) and a methanol solution (10 ml) of (CH₃COO)₂Cd.2H₂O (2.6647 g, 1 mmol) was added slowly with constant stirring on a hot plate. A white precipitate was formed and the mixture was stirred for a further 2 h. The precipitate was filtered off and dried over silica gel. It was then dissolved in dimethylsulfoxide solution (50 ml), Colourless blocks were filtered off and dried over silica gel.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms. The S atom and methyl groups of dimethylsulfoxide are disordered over two sites, with occupancies of 0.715 (4) and 0.285 (4)
	Fig. 2. The packing of (I), viewed down the a-axis, showing one layer of molecules connected by N—H···N and N—H···O hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonding have been omitted.

cis-Bis[4-amino-N-(pyrimidin-2-yl)benzenesulfonamido- κ²N,N']bis(dimethyl sulfoxide-κO)cadmium top

Crystal data top

[Cd(C₁₀H₉N₄O₂S)₂(C₂H₆OS)₂]	F(000) = 1560
M_r = 767.20	D_x = 1.669 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3503 reflections
a = 16.9168 (5) Å	θ = 2.9–27.5°
b = 15.2448 (3) Å	µ = 1.04 mm⁻¹
c = 11.8402 (3) Å	T = 150 K
V = 3053.51 (13) Å³	Block, white
Z = 4	0.22 × 0.20 × 0.18 mm

Data collection top

Nonius KappaCCD diffractometer	3503 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.088
ω scans	θ_max = 27.5°, θ_min = 3.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −21→18
T_min = 0.803, T_max = 0.835	k = −19→19
21431 measured reflections	l = −15→15

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ²(F_o²) + (0.0172P)² + 6.2081P] where P = (F_o² + 2F_c²)/3
3503 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.74 e Å⁻³
30 restraints	Δρ_min = −0.78 e Å⁻³

Crystal data top

[Cd(C₁₀H₉N₄O₂S)₂(C₂H₆OS)₂]	V = 3053.51 (13) Å³
M_r = 767.20	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 16.9168 (5) Å	µ = 1.04 mm⁻¹
b = 15.2448 (3) Å	T = 150 K
c = 11.8402 (3) Å	0.22 × 0.20 × 0.18 mm

Data collection top

Nonius KappaCCD diffractometer	3503 independent reflections
Absorption correction: multi-scan (Blessing, 1995)	2545 reflections with I > 2σ(I)
T_min = 0.803, T_max = 0.835	R_int = 0.088
21431 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	30 restraints
wR(F²) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	Δρ_max = 0.74 e Å⁻³
3503 reflections	Δρ_min = −0.78 e Å⁻³
235 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	Occ. (<1)
Cd1	0.0000	0.12725 (2)	0.2500	0.02037 (13)
S11	−0.15957 (6)	0.26178 (6)	0.36236 (8)	0.0199 (2)
O11	−0.20168 (16)	0.21509 (17)	0.2743 (2)	0.0270 (7)
O12	−0.19685 (16)	0.26244 (17)	0.4719 (2)	0.0257 (6)
N11	−0.07346 (19)	0.21814 (19)	0.3648 (3)	0.0198 (7)
N12	0.05166 (19)	0.1969 (2)	0.4215 (3)	0.0199 (7)
N13	−0.0247 (2)	0.3085 (2)	0.5150 (3)	0.0249 (8)
N14	−0.1601 (2)	0.6222 (2)	0.1768 (3)	0.0303 (8)
H14A	−0.129 (2)	0.630 (3)	0.111 (3)	0.049 (15)*
H14B	−0.204 (2)	0.655 (3)	0.204 (4)	0.050 (15)*
C11	−0.0156 (2)	0.2441 (2)	0.4378 (3)	0.0192 (8)
C12	0.1152 (2)	0.2199 (3)	0.4811 (3)	0.0262 (9)
H12	0.1637	0.1901	0.4685	0.031*
C13	0.1122 (3)	0.2854 (3)	0.5601 (4)	0.0328 (11)
H13	0.1575	0.3016	0.6026	0.039*
C14	0.0402 (3)	0.3271 (3)	0.5751 (4)	0.0329 (11)
H14	0.0367	0.3714	0.6313	0.039*
C15	−0.1503 (2)	0.3716 (2)	0.3178 (3)	0.0206 (8)
C16	−0.1968 (3)	0.4361 (3)	0.3654 (3)	0.0280 (10)
H16	−0.2269	0.4232	0.4312	0.034*
C17	−0.2005 (3)	0.5188 (3)	0.3195 (4)	0.0288 (10)
H17	−0.2336	0.5619	0.3530	0.035*
C18	−0.1556 (2)	0.5402 (2)	0.2229 (3)	0.0231 (9)
C19	−0.1065 (3)	0.4757 (3)	0.1783 (4)	0.0312 (10)
H19	−0.0739	0.4889	0.1152	0.037*
C20	−0.1045 (3)	0.3927 (3)	0.2248 (4)	0.0332 (11)
H20	−0.0711	0.3493	0.1924	0.040*
O1	−0.08770 (19)	0.01537 (18)	0.2349 (2)	0.0364 (8)
S1	−0.08063 (10)	−0.05478 (10)	0.14466 (12)	0.0277 (5)	0.715 (4)
S1'	−0.1400 (3)	−0.0149 (3)	0.1457 (3)	0.0378 (15)	0.285 (4)
C1	−0.1509 (6)	−0.0296 (6)	0.0397 (7)	0.068 (2)	0.715 (4)
H1A	−0.2036	−0.0265	0.0739	0.101*	0.715 (4)
H1B	−0.1504	−0.0753	−0.0185	0.101*	0.715 (4)
H1C	−0.1379	0.0271	0.0053	0.101*	0.715 (4)
C2	−0.1237 (6)	−0.1479 (5)	0.2028 (7)	0.051 (2)	0.715 (4)
H2A	−0.0896	−0.1710	0.2628	0.076*	0.715 (4)
H2B	−0.1304	−0.1925	0.1440	0.076*	0.715 (4)
H2C	−0.1754	−0.1327	0.2346	0.076*	0.715 (4)
C1'	−0.0900 (11)	−0.0263 (12)	0.0231 (14)	0.042 (4)	0.285 (4)
H1'1	−0.0843	0.0311	−0.0132	0.064*	0.285 (4)
H1'2	−0.1192	−0.0659	−0.0271	0.064*	0.285 (4)
H1'3	−0.0375	−0.0508	0.0384	0.064*	0.285 (4)
C2'	−0.1696 (10)	−0.1245 (11)	0.1724 (15)	0.040 (4)	0.285 (4)
H2'1	−0.1269	−0.1646	0.1512	0.060*	0.285 (4)
H2'2	−0.2169	−0.1380	0.1278	0.060*	0.285 (4)
H2'3	−0.1816	−0.1315	0.2529	0.060*	0.285 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.0263 (2)	0.0129 (2)	0.0219 (2)	0.000	−0.00159 (18)	0.000
S11	0.0156 (5)	0.0151 (5)	0.0291 (5)	−0.0010 (4)	−0.0004 (4)	0.0004 (4)
O11	0.0217 (15)	0.0207 (15)	0.0386 (17)	−0.0055 (12)	−0.0096 (13)	−0.0029 (12)
O12	0.0208 (15)	0.0236 (15)	0.0328 (15)	0.0002 (12)	0.0050 (12)	0.0048 (12)
N11	0.0178 (17)	0.0148 (16)	0.0269 (17)	0.0027 (13)	−0.0023 (15)	−0.0019 (13)
N12	0.0162 (17)	0.0201 (17)	0.0234 (16)	0.0028 (14)	0.0008 (14)	0.0010 (13)
N13	0.0215 (19)	0.0261 (18)	0.0270 (18)	−0.0002 (15)	0.0013 (15)	−0.0092 (14)
N14	0.039 (2)	0.0210 (18)	0.0309 (19)	0.0042 (18)	0.0156 (18)	0.0058 (15)
C11	0.017 (2)	0.0179 (19)	0.0223 (19)	−0.0025 (16)	0.0031 (16)	0.0003 (15)
C12	0.018 (2)	0.033 (2)	0.028 (2)	0.0020 (18)	−0.0021 (18)	0.0006 (18)
C13	0.023 (2)	0.042 (3)	0.033 (2)	−0.004 (2)	−0.0073 (19)	−0.010 (2)
C14	0.028 (3)	0.038 (3)	0.033 (2)	−0.002 (2)	−0.005 (2)	−0.017 (2)
C15	0.018 (2)	0.0148 (19)	0.029 (2)	0.0010 (17)	−0.0021 (17)	0.0018 (15)
C16	0.032 (3)	0.022 (2)	0.030 (2)	0.0020 (19)	0.0095 (19)	0.0010 (17)
C17	0.030 (2)	0.019 (2)	0.038 (2)	0.0068 (19)	0.012 (2)	−0.0014 (17)
C18	0.024 (2)	0.0173 (19)	0.028 (2)	−0.0019 (17)	−0.0015 (18)	−0.0007 (15)
C19	0.036 (3)	0.020 (2)	0.038 (2)	−0.0013 (19)	0.020 (2)	0.0011 (18)
C20	0.037 (3)	0.016 (2)	0.047 (3)	0.0023 (19)	0.019 (2)	−0.0017 (18)
O1	0.048 (2)	0.0229 (15)	0.0381 (17)	−0.0132 (15)	−0.0010 (15)	−0.0059 (13)
S1	0.0303 (11)	0.0219 (8)	0.0310 (8)	−0.0015 (7)	−0.0025 (7)	−0.0043 (6)
S1'	0.040 (3)	0.038 (3)	0.036 (2)	−0.001 (2)	0.0012 (19)	−0.0055 (18)
C1	0.074 (4)	0.066 (4)	0.063 (4)	0.014 (4)	−0.024 (4)	−0.011 (3)
C2	0.071 (4)	0.031 (3)	0.050 (4)	−0.012 (3)	0.008 (3)	−0.003 (3)
C1'	0.051 (6)	0.039 (6)	0.037 (6)	−0.004 (5)	0.005 (5)	−0.002 (4)
C2'	0.041 (6)	0.036 (6)	0.043 (6)	−0.008 (5)	0.005 (5)	−0.006 (4)

Geometric parameters (Å, º) top

Cd1—O1	2.268 (3)	C16—H16	0.9500
Cd1—O1ⁱ	2.268 (3)	C17—C18	1.412 (6)
Cd1—N11ⁱ	2.305 (3)	C17—H17	0.9500
Cd1—N11	2.305 (3)	C18—C19	1.391 (6)
Cd1—N12	2.452 (3)	C19—C20	1.380 (6)
Cd1—N12ⁱ	2.452 (3)	C19—H19	0.9500
S11—O12	1.442 (3)	C20—H20	0.9500
S11—O11	1.449 (3)	O1—S1'	1.452 (5)
S11—N11	1.602 (3)	O1—S1	1.516 (3)
S11—C15	1.762 (4)	S1—C2	1.738 (7)
N11—C11	1.364 (5)	S1—C1	1.763 (8)
N12—C12	1.333 (5)	S1'—C1'	1.689 (16)
N12—C11	1.361 (5)	S1'—C2'	1.774 (18)
N13—C14	1.339 (5)	C1—H1A	0.9800
N13—C11	1.351 (5)	C1—H1B	0.9800
N14—C18	1.366 (5)	C1—H1C	0.9800
N14—H14A	0.94 (3)	C2—H2A	0.9800
N14—H14B	0.95 (3)	C2—H2B	0.9800
C12—C13	1.369 (6)	C2—H2C	0.9800
C12—H12	0.9500	C1'—H1'1	0.9800
C13—C14	1.385 (6)	C1'—H1'2	0.9800
C13—H13	0.9500	C1'—H1'3	0.9800
C14—H14	0.9500	C2'—H2'1	0.9800
C15—C16	1.381 (5)	C2'—H2'2	0.9800
C15—C20	1.385 (6)	C2'—H2'3	0.9800
C16—C17	1.373 (6)

O1—Cd1—O1ⁱ	82.45 (16)	N13—C14—H14	118.1
O1—Cd1—N11ⁱ	139.32 (10)	C13—C14—H14	118.1
O1ⁱ—Cd1—N11ⁱ	98.40 (11)	C16—C15—C20	118.6 (4)
O1—Cd1—N11	98.40 (11)	C16—C15—S11	120.3 (3)
O1ⁱ—Cd1—N11	139.32 (10)	C20—C15—S11	120.6 (3)
N11ⁱ—Cd1—N11	106.09 (15)	C17—C16—C15	121.2 (4)
O1—Cd1—N12	128.62 (10)	C17—C16—H16	119.4
O1ⁱ—Cd1—N12	91.54 (11)	C15—C16—H16	119.4
N11ⁱ—Cd1—N12	92.06 (11)	C16—C17—C18	120.5 (4)
N11—Cd1—N12	56.20 (11)	C16—C17—H17	119.7
O1—Cd1—N12ⁱ	91.54 (11)	C18—C17—H17	119.7
O1ⁱ—Cd1—N12ⁱ	128.62 (10)	N14—C18—C19	121.9 (4)
N11ⁱ—Cd1—N12ⁱ	56.20 (11)	N14—C18—C17	120.3 (4)
N11—Cd1—N12ⁱ	92.06 (11)	C19—C18—C17	117.8 (4)
N12—Cd1—N12ⁱ	128.72 (14)	C20—C19—C18	120.7 (4)
O12—S11—O11	115.81 (17)	C20—C19—H19	119.6
O12—S11—N11	112.60 (17)	C18—C19—H19	119.6
O11—S11—N11	104.83 (17)	C19—C20—C15	121.1 (4)
O12—S11—C15	107.54 (17)	C19—C20—H20	119.4
O11—S11—C15	107.16 (17)	C15—C20—H20	119.4
N11—S11—C15	108.61 (17)	S1'—O1—S1	46.5 (2)
C11—N11—S11	122.9 (3)	S1'—O1—Cd1	134.0 (2)
C11—N11—Cd1	99.3 (2)	S1—O1—Cd1	122.32 (18)
S11—N11—Cd1	136.84 (18)	O1—S1—C2	105.3 (3)
C12—N12—C11	117.4 (3)	O1—S1—C1	106.8 (3)
C12—N12—Cd1	147.1 (3)	C2—S1—C1	100.1 (5)
C11—N12—Cd1	92.8 (2)	O1—S1'—C1'	110.7 (7)
C14—N13—C11	114.8 (3)	O1—S1'—C2'	110.0 (6)
C18—N14—H14A	114 (3)	C1'—S1'—C2'	101.4 (9)
C18—N14—H14B	114 (3)	S1'—C1'—H1'1	109.5
H14A—N14—H14B	130 (4)	S1'—C1'—H1'2	109.5
N13—C11—N12	125.1 (3)	H1'1—C1'—H1'2	109.5
N13—C11—N11	123.9 (3)	S1'—C1'—H1'3	109.5
N12—C11—N11	110.9 (3)	H1'1—C1'—H1'3	109.5
N12—C12—C13	121.6 (4)	H1'2—C1'—H1'3	109.5
N12—C12—H12	119.2	S1'—C2'—H2'1	109.5
C13—C12—H12	119.2	S1'—C2'—H2'2	109.5
C12—C13—C14	117.1 (4)	H2'1—C2'—H2'2	109.5
C12—C13—H13	121.5	S1'—C2'—H2'3	109.5
C14—C13—H13	121.5	H2'1—C2'—H2'3	109.5
N13—C14—C13	123.8 (4)	H2'2—C2'—H2'3	109.5

O12—S11—N11—C11	−52.9 (3)	N12—C12—C13—C14	−0.2 (7)
O11—S11—N11—C11	−179.7 (3)	C11—N13—C14—C13	0.9 (6)
C15—S11—N11—C11	66.1 (3)	C12—C13—C14—N13	−2.1 (7)
O12—S11—N11—Cd1	140.9 (2)	O12—S11—C15—C16	−20.1 (4)
O11—S11—N11—Cd1	14.2 (3)	O11—S11—C15—C16	105.1 (3)
C15—S11—N11—Cd1	−100.1 (3)	N11—S11—C15—C16	−142.2 (3)
O1—Cd1—N11—C11	137.0 (2)	O12—S11—C15—C20	168.7 (3)
O1ⁱ—Cd1—N11—C11	48.8 (3)	O11—S11—C15—C20	−66.1 (4)
N11ⁱ—Cd1—N11—C11	−75.9 (2)	N11—S11—C15—C20	46.6 (4)
N12—Cd1—N11—C11	5.6 (2)	C20—C15—C16—C17	2.6 (6)
N12ⁱ—Cd1—N11—C11	−131.2 (2)	S11—C15—C16—C17	−168.8 (3)
O1—Cd1—N11—S11	−54.8 (3)	C15—C16—C17—C18	−1.0 (7)
O1ⁱ—Cd1—N11—S11	−142.9 (2)	C16—C17—C18—N14	179.3 (4)
N11ⁱ—Cd1—N11—S11	92.4 (3)	C16—C17—C18—C19	−1.6 (6)
N12—Cd1—N11—S11	173.9 (3)	N14—C18—C19—C20	−178.4 (4)
N12ⁱ—Cd1—N11—S11	37.1 (3)	C17—C18—C19—C20	2.5 (6)
O1—Cd1—N12—C12	125.0 (5)	C18—C19—C20—C15	−0.9 (7)
O1ⁱ—Cd1—N12—C12	43.4 (5)	C16—C15—C20—C19	−1.7 (7)
N11ⁱ—Cd1—N12—C12	−55.0 (5)	S11—C15—C20—C19	169.7 (4)
N11—Cd1—N12—C12	−163.1 (5)	O1ⁱ—Cd1—O1—S1'	−115.6 (4)
N12ⁱ—Cd1—N12—C12	−101.8 (5)	N11ⁱ—Cd1—O1—S1'	−21.5 (4)
O1—Cd1—N12—C11	−77.5 (2)	N11—Cd1—O1—S1'	105.5 (4)
O1ⁱ—Cd1—N12—C11	−159.1 (2)	N12—Cd1—O1—S1'	158.5 (3)
N11ⁱ—Cd1—N12—C11	102.5 (2)	N12ⁱ—Cd1—O1—S1'	13.1 (4)
N11—Cd1—N12—C11	−5.6 (2)	O1ⁱ—Cd1—O1—S1	−57.01 (18)
N12ⁱ—Cd1—N12—C11	55.66 (19)	N11ⁱ—Cd1—O1—S1	37.1 (3)
C14—N13—C11—N12	2.6 (6)	N11—Cd1—O1—S1	164.1 (2)
C14—N13—C11—N11	−176.9 (4)	N12—Cd1—O1—S1	−142.92 (18)
C12—N12—C11—N13	−4.7 (6)	N12ⁱ—Cd1—O1—S1	71.8 (2)
Cd1—N12—C11—N13	−171.2 (3)	S1'—O1—S1—C2	−86.3 (4)
C12—N12—C11—N11	174.9 (3)	Cd1—O1—S1—C2	151.5 (4)
Cd1—N12—C11—N11	8.4 (3)	S1'—O1—S1—C1	19.5 (4)
S11—N11—C11—N13	0.0 (5)	Cd1—O1—S1—C1	−102.7 (4)
Cd1—N11—C11—N13	170.5 (3)	S1—O1—S1'—C1'	−45.6 (7)
S11—N11—C11—N12	−179.5 (3)	Cd1—O1—S1'—C1'	50.6 (8)
Cd1—N11—C11—N12	−9.1 (3)	S1—O1—S1'—C2'	65.6 (7)
C11—N12—C12—C13	3.3 (6)	Cd1—O1—S1'—C2'	161.8 (6)
Cd1—N12—C12—C13	157.7 (4)

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
N14—H14A···N13ⁱⁱ	0.94 (3)	2.30 (3)	3.168 (5)	152 (4)
N14—H14B···O11ⁱⁱⁱ	0.95 (3)	2.02 (3)	2.967 (5)	173 (4)

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

Experimental details

Crystal data
Chemical formula	[Cd(C₁₀H₉N₄O₂S)₂(C₂H₆OS)₂]
M_r	767.20
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	150
a, b, c (Å)	16.9168 (5), 15.2448 (3), 11.8402 (3)
V (Å³)	3053.51 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.04
Crystal size (mm)	0.22 × 0.20 × 0.18

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (Blessing, 1995)
T_min, T_max	0.803, 0.835
No. of measured, independent and observed [I > 2σ(I)] reflections	21431, 3503, 2545
R_int	0.088
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.102, 1.09
No. of reflections	3503
No. of parameters	235
No. of restraints	30
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.78

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected bond lengths (Å) top

Cd1—O1	2.268 (3)	Cd1—N12	2.452 (3)
Cd1—N11	2.305 (3)	N14—C18	1.366 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N14—H14A···N13ⁱ	0.94 (3)	2.30 (3)	3.168 (5)	152 (4)
N14—H14B···O11ⁱⁱ	0.95 (3)	2.02 (3)	2.967 (5)	173 (4)

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

Acknowledgements

The author is grateful to the Ministry of Science and Information & Communication Technology for financial support and to the School of Chemistry, Cardiff University, Wales, for crystallographic services.

References

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