cis-Bis[4-amino-N-(pyrimidin-2-yl)benzene-sulfonamido-κN,N']bis-(dimethyl sulfoxide-κO)cadmium.

The complete mol-ecule of the title compound, [Cd(C(10)H(9)N(4)O(2)S)(2)(C(2)H(6)OS)(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 dimethyl-sulfoxide mol-ecules. The resulting N(4)O(2) donor set displays a distorted trigonal-prismatic coordination geometry. The S atom and methyl groups of dimethyl-sulfoxide are disordered over two sets of sites, with site occupancies of 0.715 (4) and 0.285 (4). The crystal structure features inter-molecular 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 = 767.20

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.102

S = 1.09

3503 reflections

235 parameters

30 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.74 e Å−3

Δρmin = −0.78 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cd(C10H9N4O2S)2(C2H6OS)2]	F(000) = 1560
Mr = 767.20	Dx = 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

Nonius KappaCCD diffractometer	3503 independent reflections
Radiation source: fine-focus sealed tube	2545 reflections with I > 2σ(I)
graphite	Rint = 0.088
ω scans	θmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −21→18
Tmin = 0.803, Tmax = 0.835	k = −19→19
21431 measured reflections	l = −15→15

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(Fo2) + (0.0172P)2 + 6.2081P] where P = (Fo2 + 2Fc2)/3
3503 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.74 e Å−3
30 restraints	Δρmin = −0.78 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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)

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) ; (ii) .