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Acta Cryst. (2011). E67, m505-m506    [ doi:10.1107/S1600536811010816 ]

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

G. M. G. Hossain

Abstract top

The complete molecule of the title compound, [Cd(C10H9N4O2S)2(C2H6OS)2], is completed by the application of a twofold rotation axis. The CdII 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.

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.

Refinement top

The S atoms and methyl groups of dimethylsulfoxide were disordered. This was modelled with two different orientations and from refinement the site occupancies were 0.715 (4):0.285 (4). The H atoms were positioned geometrically and refined using in the riding model approximation, with C—H = 0.95–0.98 Å, and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C). The N—H H atoms were located from a difference map and refined freely.

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
[Figure 1] 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)
[Figure 2] 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
Mr = 767.20Dx = 1.669 Mg m−3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 3503 reflections
a = 16.9168 (5) Åθ = 2.9–27.5°
b = 15.2448 (3) ŵ = 1.04 mm−1
c = 11.8402 (3) ÅT = 150 K
V = 3053.51 (13) Å3Block, white
Z = 40.22 × 0.20 × 0.18 mm
Data collection top
Nonius KappaCCD
diffractometer		3503 independent reflections
Radiation source: fine-focus sealed tube2545 reflections with I > 2σ(I)
graphiteRint = 0.088
ω scansθmax = 27.5°, θmin = 3.2°
Absorption correction: multi-scan
(Blessing, 1995)		h = −21→18
Tmin = 0.803, Tmax = 0.835k = −19→19
21431 measured reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102H 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 parametersΔρmax = 0.74 e Å−3
30 restraintsΔρmin = −0.78 e Å−3
Crystal data top
[Cd(C10H9N4O2S)2(C2H6OS)2]V = 3053.51 (13) Å3
Mr = 767.20Z = 4
Orthorhombic, PbcnMo Kα radiation
a = 16.9168 (5) ŵ = 1.04 mm−1
b = 15.2448 (3) ÅT = 150 K
c = 11.8402 (3) Å0.22 × 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)
Tmin = 0.803, Tmax = 0.835Rint = 0.088
21431 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.102Δρmax = 0.74 e Å−3
S = 1.09Δρmin = −0.78 e Å−3
3503 reflectionsAbsolute structure: ?
235 parametersFlack parameter: ?
30 restraintsRogers parameter: ?
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
xyzUiso*/UeqOcc. (<1)
Cd10.00000.12725 (2)0.25000.02037 (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)
N120.05166 (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)
C120.1152 (2)0.2199 (3)0.4811 (3)0.0262 (9)
H120.16370.19010.46850.031*
C130.1122 (3)0.2854 (3)0.5601 (4)0.0328 (11)
H130.15750.30160.60260.039*
C140.0402 (3)0.3271 (3)0.5751 (4)0.0329 (11)
H140.03670.37140.63130.039*
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)
H16−0.22690.42320.43120.034*
C17−0.2005 (3)0.5188 (3)0.3195 (4)0.0288 (10)
H17−0.23360.56190.35300.035*
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)
H19−0.07390.48890.11520.037*
C20−0.1045 (3)0.3927 (3)0.2248 (4)0.0332 (11)
H20−0.07110.34930.19240.040*
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−0.2036−0.02650.07390.101*0.715 (4)
H1B−0.1504−0.0753−0.01850.101*0.715 (4)
H1C−0.13790.02710.00530.101*0.715 (4)
C2−0.1237 (6)−0.1479 (5)0.2028 (7)0.051 (2)0.715 (4)
H2A−0.0896−0.17100.26280.076*0.715 (4)
H2B−0.1304−0.19250.14400.076*0.715 (4)
H2C−0.1754−0.13270.23460.076*0.715 (4)
C1'−0.0900 (11)−0.0263 (12)0.0231 (14)0.042 (4)0.285 (4)
H1'1−0.08430.0311−0.01320.064*0.285 (4)
H1'2−0.1192−0.0659−0.02710.064*0.285 (4)
H1'3−0.0375−0.05080.03840.064*0.285 (4)
C2'−0.1696 (10)−0.1245 (11)0.1724 (15)0.040 (4)0.285 (4)
H2'1−0.1269−0.16460.15120.060*0.285 (4)
H2'2−0.2169−0.13800.12780.060*0.285 (4)
H2'3−0.1816−0.13150.25290.060*0.285 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cd10.0263 (2)0.0129 (2)0.0219 (2)0.000−0.00159 (18)0.000
S110.0156 (5)0.0151 (5)0.0291 (5)−0.0010 (4)−0.0004 (4)0.0004 (4)
O110.0217 (15)0.0207 (15)0.0386 (17)−0.0055 (12)−0.0096 (13)−0.0029 (12)
O120.0208 (15)0.0236 (15)0.0328 (15)0.0002 (12)0.0050 (12)0.0048 (12)
N110.0178 (17)0.0148 (16)0.0269 (17)0.0027 (13)−0.0023 (15)−0.0019 (13)
N120.0162 (17)0.0201 (17)0.0234 (16)0.0028 (14)0.0008 (14)0.0010 (13)
N130.0215 (19)0.0261 (18)0.0270 (18)−0.0002 (15)0.0013 (15)−0.0092 (14)
N140.039 (2)0.0210 (18)0.0309 (19)0.0042 (18)0.0156 (18)0.0058 (15)
C110.017 (2)0.0179 (19)0.0223 (19)−0.0025 (16)0.0031 (16)0.0003 (15)
C120.018 (2)0.033 (2)0.028 (2)0.0020 (18)−0.0021 (18)0.0006 (18)
C130.023 (2)0.042 (3)0.033 (2)−0.004 (2)−0.0073 (19)−0.010 (2)
C140.028 (3)0.038 (3)0.033 (2)−0.002 (2)−0.005 (2)−0.017 (2)
C150.018 (2)0.0148 (19)0.029 (2)0.0010 (17)−0.0021 (17)0.0018 (15)
C160.032 (3)0.022 (2)0.030 (2)0.0020 (19)0.0095 (19)0.0010 (17)
C170.030 (2)0.019 (2)0.038 (2)0.0068 (19)0.012 (2)−0.0014 (17)
C180.024 (2)0.0173 (19)0.028 (2)−0.0019 (17)−0.0015 (18)−0.0007 (15)
C190.036 (3)0.020 (2)0.038 (2)−0.0013 (19)0.020 (2)0.0011 (18)
C200.037 (3)0.016 (2)0.047 (3)0.0023 (19)0.019 (2)−0.0017 (18)
O10.048 (2)0.0229 (15)0.0381 (17)−0.0132 (15)−0.0010 (15)−0.0059 (13)
S10.0303 (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)
C10.074 (4)0.066 (4)0.063 (4)0.014 (4)−0.024 (4)−0.011 (3)
C20.071 (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, °) top
Cd1—O12.268 (3)C16—H160.9500
Cd1—O1i2.268 (3)C17—C181.412 (6)
Cd1—N11i2.305 (3)C17—H170.9500
Cd1—N112.305 (3)C18—C191.391 (6)
Cd1—N122.452 (3)C19—C201.380 (6)
Cd1—N12i2.452 (3)C19—H190.9500
S11—O121.442 (3)C20—H200.9500
S11—O111.449 (3)O1—S1'1.452 (5)
S11—N111.602 (3)O1—S11.516 (3)
S11—C151.762 (4)S1—C21.738 (7)
N11—C111.364 (5)S1—C11.763 (8)
N12—C121.333 (5)S1'—C1'1.689 (16)
N12—C111.361 (5)S1'—C2'1.774 (18)
N13—C141.339 (5)C1—H1A0.9800
N13—C111.351 (5)C1—H1B0.9800
N14—C181.366 (5)C1—H1C0.9800
N14—H14A0.94 (3)C2—H2A0.9800
N14—H14B0.95 (3)C2—H2B0.9800
C12—C131.369 (6)C2—H2C0.9800
C12—H120.9500C1'—H1'10.9800
C13—C141.385 (6)C1'—H1'20.9800
C13—H130.9500C1'—H1'30.9800
C14—H140.9500C2'—H2'10.9800
C15—C161.381 (5)C2'—H2'20.9800
C15—C201.385 (6)C2'—H2'30.9800
C16—C171.373 (6)
O1—Cd1—O1i82.45 (16)N13—C14—H14118.1
O1—Cd1—N11i139.32 (10)C13—C14—H14118.1
O1i—Cd1—N11i98.40 (11)C16—C15—C20118.6 (4)
O1—Cd1—N1198.40 (11)C16—C15—S11120.3 (3)
O1i—Cd1—N11139.32 (10)C20—C15—S11120.6 (3)
N11i—Cd1—N11106.09 (15)C17—C16—C15121.2 (4)
O1—Cd1—N12128.62 (10)C17—C16—H16119.4
O1i—Cd1—N1291.54 (11)C15—C16—H16119.4
N11i—Cd1—N1292.06 (11)C16—C17—C18120.5 (4)
N11—Cd1—N1256.20 (11)C16—C17—H17119.7
O1—Cd1—N12i91.54 (11)C18—C17—H17119.7
O1i—Cd1—N12i128.62 (10)N14—C18—C19121.9 (4)
N11i—Cd1—N12i56.20 (11)N14—C18—C17120.3 (4)
N11—Cd1—N12i92.06 (11)C19—C18—C17117.8 (4)
N12—Cd1—N12i128.72 (14)C20—C19—C18120.7 (4)
O12—S11—O11115.81 (17)C20—C19—H19119.6
O12—S11—N11112.60 (17)C18—C19—H19119.6
O11—S11—N11104.83 (17)C19—C20—C15121.1 (4)
O12—S11—C15107.54 (17)C19—C20—H20119.4
O11—S11—C15107.16 (17)C15—C20—H20119.4
N11—S11—C15108.61 (17)S1'—O1—S146.5 (2)
C11—N11—S11122.9 (3)S1'—O1—Cd1134.0 (2)
C11—N11—Cd199.3 (2)S1—O1—Cd1122.32 (18)
S11—N11—Cd1136.84 (18)O1—S1—C2105.3 (3)
C12—N12—C11117.4 (3)O1—S1—C1106.8 (3)
C12—N12—Cd1147.1 (3)C2—S1—C1100.1 (5)
C11—N12—Cd192.8 (2)O1—S1'—C1'110.7 (7)
C14—N13—C11114.8 (3)O1—S1'—C2'110.0 (6)
C18—N14—H14A114 (3)C1'—S1'—C2'101.4 (9)
C18—N14—H14B114 (3)S1'—C1'—H1'1109.5
H14A—N14—H14B130 (4)S1'—C1'—H1'2109.5
N13—C11—N12125.1 (3)H1'1—C1'—H1'2109.5
N13—C11—N11123.9 (3)S1'—C1'—H1'3109.5
N12—C11—N11110.9 (3)H1'1—C1'—H1'3109.5
N12—C12—C13121.6 (4)H1'2—C1'—H1'3109.5
N12—C12—H12119.2S1'—C2'—H2'1109.5
C13—C12—H12119.2S1'—C2'—H2'2109.5
C12—C13—C14117.1 (4)H2'1—C2'—H2'2109.5
C12—C13—H13121.5S1'—C2'—H2'3109.5
C14—C13—H13121.5H2'1—C2'—H2'3109.5
N13—C14—C13123.8 (4)H2'2—C2'—H2'3109.5
O12—S11—N11—C11−52.9 (3)N12—C12—C13—C14−0.2 (7)
O11—S11—N11—C11−179.7 (3)C11—N13—C14—C130.9 (6)
C15—S11—N11—C1166.1 (3)C12—C13—C14—N13−2.1 (7)
O12—S11—N11—Cd1140.9 (2)O12—S11—C15—C16−20.1 (4)
O11—S11—N11—Cd114.2 (3)O11—S11—C15—C16105.1 (3)
C15—S11—N11—Cd1−100.1 (3)N11—S11—C15—C16−142.2 (3)
O1—Cd1—N11—C11137.0 (2)O12—S11—C15—C20168.7 (3)
O1i—Cd1—N11—C1148.8 (3)O11—S11—C15—C20−66.1 (4)
N11i—Cd1—N11—C11−75.9 (2)N11—S11—C15—C2046.6 (4)
N12—Cd1—N11—C115.6 (2)C20—C15—C16—C172.6 (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—N14179.3 (4)
N11i—Cd1—N11—S1192.4 (3)C16—C17—C18—C19−1.6 (6)
N12—Cd1—N11—S11173.9 (3)N14—C18—C19—C20−178.4 (4)
N12i—Cd1—N11—S1137.1 (3)C17—C18—C19—C202.5 (6)
O1—Cd1—N12—C12125.0 (5)C18—C19—C20—C15−0.9 (7)
O1i—Cd1—N12—C1243.4 (5)C16—C15—C20—C19−1.7 (7)
N11i—Cd1—N12—C12−55.0 (5)S11—C15—C20—C19169.7 (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—C11102.5 (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—C1155.66 (19)N11i—Cd1—O1—S137.1 (3)
C14—N13—C11—N122.6 (6)N11—Cd1—O1—S1164.1 (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—S171.8 (2)
Cd1—N12—C11—N13−171.2 (3)S1'—O1—S1—C2−86.3 (4)
C12—N12—C11—N11174.9 (3)Cd1—O1—S1—C2151.5 (4)
Cd1—N12—C11—N118.4 (3)S1'—O1—S1—C119.5 (4)
S11—N11—C11—N130.0 (5)Cd1—O1—S1—C1−102.7 (4)
Cd1—N11—C11—N13170.5 (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—C133.3 (6)Cd1—O1—S1'—C2'161.8 (6)
Cd1—N12—C12—C13157.7 (4)
Symmetry codes: (i) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N14—H14A···N13ii0.94 (3)2.30 (3)3.168 (5)152 (4)
N14—H14B···O11iii0.95 (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.
Table 1
Selected geometric parameters (Å) top
Cd1—O12.268 (3)Cd1—N122.452 (3)
Cd1—N112.305 (3)N14—C181.366 (5)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N14—H14A···N13i0.94 (3)2.30 (3)3.168 (5)152 (4)
N14—H14B···O11ii0.95 (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 top

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
References top

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