Bis{2-[4-(methyl­sulfan­yl)phen­yl]-1H-benzimidazol-3-ium} tetra­bromido­cadmate(II) ethanol monosolvate

M N Manjunatha; Mohamed Ziaulla; Noor Shahina Begum; K R Nagasundara

doi:10.1107/S1600536811018058

. 2011 May 20;67(Pt 6):m771. doi: 10.1107/S1600536811018058

Bis{2-[4-(methylsulfanyl)phenyl]-1H-benzimidazol-3-ium} tetrabromidocadmate(II) ethanol monosolvate

M N Manjunatha ^a, Mohamed Ziaulla ^a, Noor Shahina Begum ^a,^*, K R Nagasundara ^a

PMCID: PMC3120599 PMID: 21754655

Abstract

In the anion of the title compound, (C₁₄H₁₃N₂S)₂[CdBr₄]·C₂H₅OH, the Cd^II atom is in a distorted tetrahedral environment and one of the Br atoms is disordered over three sites with site-occupancy factors of 0.828 (5), 0.106 (3) and 0.068 (4). In the crystal, intermolecular N—H⋯O, C—H⋯O and N—H⋯Br interactions result in a two-dimensional polymeric network extending parallel to (010).

Related literature

For general background to benzimidazole derivatives, see: Huang & Scarborough (1999 ▶); Preston (1974 ▶); Zarrinmayeh et al. (1998 ▶); Zhu et al. (2000 ▶). For related structures, see: Ziaulla et al. (2011 ▶). For hydrogen bonding, see: Bernstein et al. (1995 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

(C₁₄H₁₃N₂S)₂[CdBr₄]·C₂H₆O
M _r = 960.76
Orthorhombic,
a = 22.1321 (15) Å
b = 13.8746 (10) Å
c = 22.2594 (16) Å
V = 6835.3 (8) Å³
Z = 8
Mo Kα radiation
μ = 5.47 mm⁻¹
T = 123 K
0.20 × 0.18 × 0.18 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.408, T _max = 0.439
93968 measured reflections
7467 independent reflections
5951 reflections with I > 2σ(I)
R _int = 0.084

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.079
S = 0.79
7467 reflections
407 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1996) ▶; software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018058/ds2093sup1.cif

e-67-0m771-sup1.cif^{(28.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018058/ds2093Isup2.hkl

e-67-0m771-Isup2.hkl^{(358.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Br3	0.79 (7)	2.51 (7)	3.272 (5)	164 (5)
N2—H2N⋯Br2ⁱ	0.81 (7)	2.50 (7)	3.267 (4)	160 (5)
N4—H4N⋯O1ⁱⁱ	0.83 (7)	1.88 (7)	2.679 (6)	161 (6)
C4—H4⋯O1ⁱⁱ	0.95	2.55	3.464 (8)	160

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance and Department of Science and Technology, (DST), India, for the data collection facility under the IRHPA–DST program. MNM thanks the M. S. Ramaiah Institute of Technology, Bangalore, for their support and encouragement.

supplementary crystallographic information

Comment

Benzimidazole derivatives are effective against the human cytomegalo virus (HCMV) (Zhu et al., 2000) and are also efficient selective neuropeptide Y Y1 receptor antagonists (Zarrinmayeh et al., 1998). In addition, benzimidazole derivatives exhibit a number of important pharmacological properties, such as antihistaminic, anti-ulcerative, antiallergic and antipyretic. The described methods for the synthesis of benzimidazoles make use of solid-phase synthesis via o-nitroanilines (Preston et al., 1974; Huang et al., 1999) or the condensation of o-phenylenediamines with carboxylic acid derivatives, aldehydes and aryl halides. The benzimidazole derivative has been used as a ligand for complexation with cadmium metal to give the above metal complex. In the title compound, as shown in Fig. 1, there are two cation,one tetrabormocadmate(II) anion and an ethanol molecule in the asymmetric unit. One of the coordinated bromine atom Br4 of the anion is disordered over three sites (Br4A/Br4B/Br4C) with site occupancy factors 0.83, 0,11 and 0.06 resulting in one major and two minor components.The Cd^II atom has a distorted tetrahedral geometry, coordinating with four terminal bromine atoms with the bond lengths in the range 2.5616 (7)Å to 2.6177 (6) Å. The Br—Cd—Br bond angles are between 111.37 (3)° and 107.14 (2)°, The benzimidazole and thiomethyl phenyl rings are virtually planar and inclined at an dihedral angle 5.19 (2)°. The molecular structure is primarly stablised by intramolecular N—H···Br interactions. The bond lengths and angles for the benzimidazole moiety of the molecule are in good agreement, within experimental errors, with those observed in other benzimidazole derivatives (Ziaulla et al., 2011). Further, the crystal structure is stabilized by intermolecular N—H···O, C—H···O and N—H···Br hydrogen bonds.

Experimental

An ethanolic solution (15 ml) of the 2-(4-Methyl sulfanyl phenyl)-1H- benzimidazole) (0.960 mg, 2 mmol) was added to a solution of cadmium(II) bromide (0.272 mg, 1 mmol) in ethanol (25 ml). The mixture was then treated with 48% HBr (2–3 ml) followed by liquid Br₂ (2–3 ml). The mixture was refluxed for nearly six hours during which yellow crystals suitable for X-ray analysis were obtained. The crystals were washed with cold ethanol and dried in vacuum over P₂O₅. (yield 1.23 mg, 85%).