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

Manjunatha, M.N.; Ziaulla, M.; Begum, N.S.; Nagasundara, K.R.

doi:10.1107/S1600536811018058

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m771

doi:10.1107/S1600536811018058

Open

access

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

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

^aDepartment of Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India
^*Correspondence e-mail: noorsb@rediffmail.com

(Received 12 February 2011; accepted 12 May 2011; online 20 May 2011)

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, P b c a
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[F² > 2σ(F²)] = 0.034
wR(F²) = 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

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
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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 top

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%).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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).

Figures top

	Fig. 1. ORTEP (Farrugia, 1997) view of the title compound, showing 50% probability ellipsoids and the atom numbering scheme.
	Fig. 2. A unit cell packing of the title compound showing intermolecular interactions with dotted lines. H-atoms not involved in hydrogen bonding have been excluded.

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

Crystal data top

(C₁₄H₁₃N₂S)₂[CdBr₄]·C₂H₆O	F(000) = 3744
M_r = 960.76	D_x = 1.867 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 7467 reflections
a = 22.1321 (15) Å	θ = 1.8–27.0°
b = 13.8746 (10) Å	µ = 5.47 mm⁻¹
c = 22.2594 (16) Å	T = 123 K
V = 6835.3 (8) Å³	Block, yellow
Z = 8	0.20 × 0.18 × 0.18 mm

Data collection top

Bruker SMART APEX CCD detector diffractometer	7467 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5951 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.084
ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
T_min = 0.408, T_max = 0.439	k = −17→17
93968 measured reflections	l = −28→28

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 0.79	w = 1/[σ²(F_o²) + (0.0318P)² + 49.2262P] where P = (F_o² + 2F_c²)/3
7467 reflections	(Δ/σ)_max = 0.001
407 parameters	Δρ_max = 0.87 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

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

Data collection top

Bruker SMART APEX CCD detector diffractometer	7467 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5951 reflections with I > 2σ(I)
T_min = 0.408, T_max = 0.439	R_int = 0.084
93968 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 0.79	w = 1/[σ²(F_o²) + (0.0318P)² + 49.2262P] where P = (F_o² + 2F_c²)/3
7467 reflections	Δρ_max = 0.87 e Å⁻³
407 parameters	Δρ_min = −0.69 e Å⁻³

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.348496 (11)	0.21808 (2)	0.361336 (13)	0.02080 (7)
Br1	0.326079 (18)	0.11642 (3)	0.26634 (2)	0.02983 (11)
Br2	0.399388 (19)	0.11298 (3)	0.441935 (19)	0.02699 (10)
Br3	0.425609 (17)	0.35205 (3)	0.330092 (18)	0.02342 (9)
Br4A	0.25223 (3)	0.29865 (10)	0.40079 (6)	0.0445 (4)	0.828 (5)
Br4B	0.2514 (2)	0.2592 (6)	0.4250 (3)	0.0302 (17)*	0.106 (3)
Br4C	0.2621 (4)	0.3426 (10)	0.3968 (3)	0.028 (3)*	0.068 (4)
S1	0.11862 (4)	0.36770 (8)	0.16669 (5)	0.0261 (2)
S2	0.64644 (5)	0.09455 (8)	0.43078 (5)	0.0259 (2)
N1	0.42680 (14)	0.3486 (2)	0.18313 (16)	0.0184 (7)
H1N	0.4190 (18)	0.346 (3)	0.217 (2)	0.011 (11)*
N2	0.41912 (14)	0.3569 (2)	0.08615 (16)	0.0172 (7)
H2N	0.405 (2)	0.362 (3)	0.051 (2)	0.022 (12)*
N3	0.45281 (14)	0.1032 (2)	0.19059 (16)	0.0186 (7)
H3N	0.429 (2)	0.100 (4)	0.218 (2)	0.038 (15)*
N4	0.53761 (15)	0.1058 (2)	0.14156 (16)	0.0208 (7)
H4N	0.575 (2)	0.103 (3)	0.136 (2)	0.034 (13)*
O1	0.15209 (14)	0.1207 (3)	0.39651 (19)	0.0460 (9)
H1	0.1697	0.1741	0.3994	0.069*
C1	0.72537 (18)	0.1017 (3)	0.4124 (2)	0.0306 (10)
H1A	0.7375	0.0434	0.3907	0.046*
H1B	0.7491	0.1073	0.4494	0.046*
H1C	0.7326	0.1583	0.3871	0.046*
C2	0.61084 (17)	0.0962 (3)	0.36033 (19)	0.0194 (8)
C3	0.64147 (17)	0.0996 (3)	0.3056 (2)	0.0229 (9)
H3	0.6844	0.1015	0.3049	0.027*
C4	0.60955 (16)	0.1002 (3)	0.25272 (19)	0.0214 (8)
H4	0.6307	0.1015	0.2156	0.026*
C5	0.54640 (17)	0.0990 (3)	0.25268 (18)	0.0184 (8)
C6	0.51621 (16)	0.0957 (3)	0.30770 (18)	0.0196 (8)
H6	0.4733	0.0944	0.3084	0.024*
C7	0.54755 (17)	0.0943 (3)	0.36072 (19)	0.0212 (8)
H7	0.5264	0.0920	0.3978	0.025*
C8	0.51336 (16)	0.1021 (3)	0.19612 (18)	0.0181 (8)
C9	0.49220 (16)	0.1105 (3)	0.09894 (18)	0.0205 (8)
C10	0.43776 (17)	0.1091 (3)	0.13000 (18)	0.0186 (8)
C11	0.38240 (17)	0.1154 (3)	0.1008 (2)	0.0234 (9)
H11	0.3452	0.1145	0.1222	0.028*
C12	0.38445 (18)	0.1230 (3)	0.0395 (2)	0.0252 (9)
H12	0.3476	0.1283	0.0179	0.030*
C13	0.43935 (19)	0.1233 (3)	0.0071 (2)	0.0279 (9)
H13	0.4386	0.1280	−0.0354	0.034*
C14	0.49412 (19)	0.1170 (3)	0.0366 (2)	0.0271 (9)
H14	0.5313	0.1170	0.0154	0.033*
C15	0.08636 (17)	0.3561 (3)	0.0930 (2)	0.0263 (9)
H15A	0.1001	0.4096	0.0677	0.039*
H15B	0.0422	0.3575	0.0959	0.039*
H15C	0.0992	0.2949	0.0751	0.039*
C16	0.19661 (16)	0.3623 (3)	0.15389 (19)	0.0209 (8)
C17	0.22338 (16)	0.3494 (3)	0.09802 (19)	0.0203 (8)
H17	0.1987	0.3427	0.0633	0.024*
C18	0.28564 (16)	0.3464 (3)	0.09239 (18)	0.0197 (8)
H18	0.3034	0.3379	0.0539	0.024*
C19	0.32244 (16)	0.3556 (3)	0.14304 (18)	0.0182 (8)
C20	0.29562 (17)	0.3688 (3)	0.19946 (19)	0.0233 (8)
H20	0.3202	0.3754	0.2342	0.028*
C21	0.23346 (18)	0.3722 (3)	0.2046 (2)	0.0253 (9)
H21	0.2155	0.3813	0.2430	0.030*
C22	0.38773 (16)	0.3542 (3)	0.13739 (17)	0.0172 (7)
C23	0.48535 (16)	0.3490 (3)	0.16087 (18)	0.0180 (8)
C24	0.54085 (17)	0.3457 (3)	0.1900 (2)	0.0253 (9)
H24	0.5440	0.3420	0.2325	0.030*
C25	0.59109 (18)	0.3483 (3)	0.1532 (2)	0.0301 (10)
H25	0.6301	0.3463	0.1710	0.036*
C26	0.58653 (17)	0.3537 (3)	0.0909 (2)	0.0273 (9)
H26	0.6225	0.3555	0.0676	0.033*
C27	0.53125 (17)	0.3566 (3)	0.0619 (2)	0.0235 (9)
H27	0.5280	0.3602	0.0194	0.028*
C28	0.48085 (16)	0.3539 (3)	0.09907 (18)	0.0174 (7)
C29	0.22850 (16)	0.0414 (3)	0.45435 (18)	0.0460 (13)
H29A	0.2535	0.0992	0.4589	0.069*
H29B	0.2542	−0.0160	0.4559	0.069*
H29C	0.1988	0.0388	0.4869	0.069*
C30	0.19621 (16)	0.0449 (3)	0.39490 (18)	0.0428 (12)
H30A	0.2256	0.0570	0.3622	0.051*
H30B	0.1761	−0.0176	0.3871	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.01375 (12)	0.02995 (15)	0.01871 (15)	0.00150 (11)	−0.00061 (11)	−0.00047 (12)
Br1	0.01902 (18)	0.0486 (3)	0.0218 (2)	−0.00511 (18)	0.00033 (16)	−0.00842 (19)
Br2	0.0268 (2)	0.0371 (2)	0.0170 (2)	0.00091 (17)	−0.00239 (16)	0.00446 (17)
Br3	0.02397 (19)	0.0292 (2)	0.0171 (2)	−0.00377 (16)	−0.00242 (16)	0.00177 (16)
Br4A	0.0152 (3)	0.0288 (7)	0.0897 (8)	0.0002 (3)	0.0138 (3)	−0.0106 (5)
S1	0.0164 (4)	0.0349 (6)	0.0269 (6)	0.0037 (4)	0.0056 (4)	0.0071 (5)
S2	0.0231 (5)	0.0303 (5)	0.0241 (6)	0.0015 (4)	−0.0071 (4)	−0.0005 (4)
N1	0.0197 (16)	0.0236 (17)	0.0121 (18)	0.0033 (13)	−0.0002 (13)	0.0013 (14)
N2	0.0143 (14)	0.0235 (16)	0.0137 (18)	−0.0019 (12)	−0.0029 (13)	−0.0010 (13)
N3	0.0138 (15)	0.0223 (17)	0.0196 (19)	−0.0024 (12)	0.0015 (13)	0.0029 (14)
N4	0.0147 (15)	0.0261 (17)	0.0218 (19)	0.0031 (13)	0.0018 (13)	0.0018 (14)
O1	0.0256 (16)	0.052 (2)	0.060 (3)	0.0025 (15)	−0.0133 (17)	−0.010 (2)
C1	0.0209 (19)	0.031 (2)	0.040 (3)	0.0003 (17)	−0.0128 (19)	0.002 (2)
C2	0.0216 (18)	0.0139 (17)	0.023 (2)	0.0013 (14)	−0.0059 (16)	0.0002 (15)
C3	0.0143 (17)	0.024 (2)	0.030 (2)	0.0039 (15)	0.0001 (16)	0.0005 (17)
C4	0.0147 (17)	0.027 (2)	0.023 (2)	0.0007 (15)	0.0014 (15)	−0.0019 (17)
C5	0.0180 (17)	0.0178 (18)	0.019 (2)	0.0018 (14)	0.0005 (15)	0.0007 (15)
C6	0.0149 (17)	0.0217 (19)	0.022 (2)	0.0015 (14)	0.0024 (15)	−0.0014 (16)
C7	0.0180 (17)	0.0232 (19)	0.022 (2)	0.0003 (15)	0.0050 (16)	−0.0001 (16)
C8	0.0168 (17)	0.0167 (18)	0.021 (2)	−0.0006 (14)	0.0010 (15)	0.0025 (16)
C9	0.0180 (18)	0.0240 (19)	0.020 (2)	0.0044 (15)	−0.0004 (15)	−0.0003 (16)
C10	0.0219 (18)	0.0176 (18)	0.016 (2)	−0.0021 (14)	0.0003 (15)	0.0011 (15)
C11	0.0181 (18)	0.0229 (19)	0.029 (2)	−0.0014 (15)	−0.0034 (16)	−0.0016 (17)
C12	0.026 (2)	0.024 (2)	0.026 (2)	0.0024 (16)	−0.0112 (17)	−0.0067 (17)
C13	0.035 (2)	0.033 (2)	0.015 (2)	0.0056 (18)	−0.0035 (17)	−0.0049 (18)
C14	0.027 (2)	0.031 (2)	0.023 (2)	0.0022 (17)	0.0060 (17)	−0.0015 (18)
C15	0.0160 (18)	0.034 (2)	0.029 (2)	0.0018 (16)	0.0002 (16)	0.0008 (19)
C16	0.0153 (17)	0.0181 (18)	0.029 (2)	0.0021 (14)	0.0042 (16)	0.0044 (16)
C17	0.0163 (17)	0.0217 (19)	0.023 (2)	−0.0010 (14)	−0.0014 (16)	−0.0011 (16)
C18	0.0169 (17)	0.0224 (19)	0.020 (2)	−0.0003 (14)	0.0039 (15)	0.0006 (16)
C19	0.0182 (17)	0.0171 (17)	0.019 (2)	0.0020 (14)	0.0016 (15)	0.0000 (15)
C20	0.0213 (19)	0.028 (2)	0.021 (2)	0.0022 (16)	0.0011 (16)	0.0035 (17)
C21	0.0239 (19)	0.032 (2)	0.020 (2)	0.0040 (16)	0.0048 (17)	0.0045 (18)
C22	0.0224 (18)	0.0138 (17)	0.015 (2)	−0.0001 (14)	0.0015 (15)	−0.0008 (15)
C23	0.0163 (17)	0.0182 (18)	0.019 (2)	−0.0007 (14)	−0.0027 (15)	−0.0016 (16)
C24	0.0214 (19)	0.031 (2)	0.024 (2)	0.0006 (16)	−0.0071 (17)	0.0011 (18)
C25	0.0187 (19)	0.035 (2)	0.036 (3)	−0.0032 (17)	−0.0103 (18)	0.000 (2)
C26	0.0157 (18)	0.038 (2)	0.028 (2)	0.0009 (16)	0.0009 (16)	0.0081 (19)
C27	0.0196 (18)	0.027 (2)	0.025 (2)	0.0007 (15)	0.0017 (16)	0.0024 (17)
C28	0.0163 (17)	0.0173 (17)	0.019 (2)	−0.0005 (14)	−0.0048 (15)	−0.0011 (15)
C29	0.048 (3)	0.054 (3)	0.036 (3)	−0.005 (3)	−0.006 (2)	−0.003 (3)
C30	0.031 (2)	0.049 (3)	0.049 (3)	0.007 (2)	−0.007 (2)	−0.009 (3)

Geometric parameters (Å, º) top

Cd1—Br4A	2.5612 (6)	C9—C14	1.390 (6)
Cd1—Br2	2.5717 (5)	C9—C10	1.389 (5)
Cd1—Br1	2.5898 (5)	C10—C11	1.390 (5)
Cd1—Br3	2.6175 (5)	C11—C12	1.370 (6)
Cd1—Br4B	2.636 (5)	C11—H11	0.9500
Cd1—Br4C	2.695 (8)	C12—C13	1.413 (6)
Br4A—Br4C	0.654 (14)	C12—H12	0.9500
Br4A—Br4B	0.768 (8)	C13—C14	1.382 (6)
Br4B—Br4C	1.338 (16)	C13—H13	0.9500
S1—C16	1.751 (4)	C14—H14	0.9500
S1—C15	1.797 (4)	C15—H15A	0.9800
S2—C2	1.755 (4)	C15—H15B	0.9800
S2—C1	1.797 (4)	C15—H15C	0.9800
N1—C22	1.338 (5)	C16—C17	1.389 (6)
N1—C23	1.387 (5)	C16—C21	1.400 (6)
N1—H1N	0.77 (4)	C17—C18	1.384 (5)
N2—C22	1.336 (5)	C17—H17	0.9500
N2—C28	1.397 (4)	C18—C19	1.397 (5)
N2—H2N	0.84 (5)	C18—H18	0.9500
N3—C8	1.346 (5)	C19—C20	1.401 (6)
N3—C10	1.392 (5)	C19—C22	1.451 (5)
N3—H3N	0.81 (5)	C20—C21	1.381 (5)
N4—C8	1.329 (5)	C20—H20	0.9500
N4—C9	1.384 (5)	C21—H21	0.9500
N4—H4N	0.84 (5)	C23—C28	1.381 (5)
O1—C30	1.435 (5)	C23—C24	1.390 (5)
O1—H1	0.8400	C24—C25	1.382 (6)
C1—H1A	0.9800	C24—H24	0.9500
C1—H1B	0.9800	C25—C26	1.392 (6)
C1—H1C	0.9800	C25—H25	0.9500
C2—C3	1.395 (6)	C26—C27	1.384 (5)
C2—C7	1.401 (5)	C26—H26	0.9500
C3—C4	1.373 (6)	C27—C28	1.390 (5)
C3—H3	0.9500	C27—H27	0.9500
C4—C5	1.398 (5)	C29—C30	1.5047
C4—H4	0.9500	C29—H29A	0.9800
C5—C6	1.396 (5)	C29—H29B	0.9800
C5—C8	1.457 (5)	C29—H29C	0.9800
C6—C7	1.369 (6)	C30—H30A	0.9900
C6—H6	0.9500	C30—H30B	0.9900
C7—H7	0.9500

Br4A—Cd1—Br2	111.87 (4)	C11—C10—N3	131.9 (4)
Br4A—Cd1—Br1	111.00 (2)	C12—C11—C10	116.2 (4)
Br2—Cd1—Br1	110.162 (19)	C12—C11—H11	121.9
Br4A—Cd1—Br3	108.88 (4)	C10—C11—H11	121.9
Br2—Cd1—Br3	107.605 (16)	C11—C12—C13	122.5 (4)
Br1—Cd1—Br3	107.142 (17)	C11—C12—H12	118.8
Br4A—Cd1—Br4B	16.92 (16)	C13—C12—H12	118.8
Br2—Cd1—Br4B	96.01 (16)	C14—C13—C12	120.8 (4)
Br1—Cd1—Br4B	113.60 (11)	C14—C13—H13	119.6
Br3—Cd1—Br4B	121.39 (17)	C12—C13—H13	119.6
Br4A—Cd1—Br4C	14.0 (3)	C13—C14—C9	116.8 (4)
Br2—Cd1—Br4C	118.01 (18)	C13—C14—H14	121.6
Br1—Cd1—Br4C	116.9 (2)	C9—C14—H14	121.6
Br3—Cd1—Br4C	94.9 (3)	S1—C15—H15A	109.5
Br4B—Cd1—Br4C	29.0 (3)	S1—C15—H15B	109.5
Br4C—Br4A—Br4B	140.2 (8)	H15A—C15—H15B	109.5
Br4C—Br4A—Cd1	94.7 (6)	S1—C15—H15C	109.5
Br4B—Br4A—Cd1	87.1 (4)	H15A—C15—H15C	109.5
Br4A—Br4B—Br4C	18.3 (5)	H15B—C15—H15C	109.5
Br4A—Br4B—Cd1	76.0 (4)	C17—C16—C21	119.1 (3)
Br4C—Br4B—Cd1	77.9 (4)	C17—C16—S1	124.9 (3)
Br4A—Br4C—Br4B	21.6 (5)	C21—C16—S1	116.0 (3)
Br4A—Br4C—Cd1	71.3 (6)	C18—C17—C16	120.6 (4)
Br4B—Br4C—Cd1	73.0 (5)	C18—C17—H17	119.7
C16—S1—C15	103.9 (2)	C16—C17—H17	119.7
C2—S2—C1	103.4 (2)	C17—C18—C19	120.3 (4)
C22—N1—C23	109.4 (3)	C17—C18—H18	119.9
C22—N1—H1N	127 (3)	C19—C18—H18	119.9
C23—N1—H1N	124 (3)	C18—C19—C20	119.2 (3)
C22—N2—C28	109.4 (3)	C18—C19—C22	120.6 (4)
C22—N2—H2N	127 (3)	C20—C19—C22	120.1 (4)
C28—N2—H2N	124 (3)	C21—C20—C19	120.1 (4)
C8—N3—C10	109.1 (3)	C21—C20—H20	120.0
C8—N3—H3N	126 (4)	C19—C20—H20	120.0
C10—N3—H3N	125 (4)	C20—C21—C16	120.6 (4)
C8—N4—C9	109.6 (3)	C20—C21—H21	119.7
C8—N4—H4N	122 (3)	C16—C21—H21	119.7
C9—N4—H4N	128 (3)	N2—C22—N1	108.4 (3)
C30—O1—H1	109.5	N2—C22—C19	126.3 (4)
S2—C1—H1A	109.5	N1—C22—C19	125.3 (4)
S2—C1—H1B	109.5	C28—C23—N1	106.8 (3)
H1A—C1—H1B	109.5	C28—C23—C24	122.0 (4)
S2—C1—H1C	109.5	N1—C23—C24	131.2 (4)
H1A—C1—H1C	109.5	C25—C24—C23	115.7 (4)
H1B—C1—H1C	109.5	C25—C24—H24	122.1
C3—C2—C7	119.5 (4)	C23—C24—H24	122.1
C3—C2—S2	124.2 (3)	C24—C25—C26	122.3 (4)
C7—C2—S2	116.3 (3)	C24—C25—H25	118.9
C4—C3—C2	119.9 (3)	C26—C25—H25	118.9
C4—C3—H3	120.0	C27—C26—C25	122.0 (4)
C2—C3—H3	120.0	C27—C26—H26	119.0
C3—C4—C5	121.0 (4)	C25—C26—H26	119.0
C3—C4—H4	119.5	C28—C27—C26	115.5 (4)
C5—C4—H4	119.5	C28—C27—H27	122.2
C6—C5—C4	118.6 (4)	C26—C27—H27	122.2
C6—C5—C8	121.3 (3)	C23—C28—C27	122.5 (3)
C4—C5—C8	120.1 (4)	C23—C28—N2	106.1 (3)
C7—C6—C5	120.9 (3)	C27—C28—N2	131.4 (4)
C7—C6—H6	119.5	C30—C29—H29A	109.5
C5—C6—H6	119.5	C30—C29—H29B	109.5
C6—C7—C2	120.1 (4)	H29A—C29—H29B	109.5
C6—C7—H7	120.0	C30—C29—H29C	109.5
C2—C7—H7	120.0	H29A—C29—H29C	109.5
N4—C8—N3	108.6 (3)	H29B—C29—H29C	109.5
N4—C8—C5	126.0 (3)	O1—C30—C29	108.9 (2)
N3—C8—C5	125.4 (4)	O1—C30—H30A	109.9
N4—C9—C14	131.7 (4)	C29—C30—H30A	109.9
N4—C9—C10	106.7 (3)	O1—C30—H30B	109.9
C14—C9—C10	121.6 (4)	C29—C30—H30B	109.9
C9—C10—C11	122.1 (4)	H30A—C30—H30B	108.3
C9—C10—N3	106.0 (3)

Br2—Cd1—Br4A—Br4C	118.8 (7)	C8—N4—C9—C14	178.9 (4)
Br1—Cd1—Br4A—Br4C	−117.7 (7)	C8—N4—C9—C10	−0.2 (4)
Br3—Cd1—Br4A—Br4C	0.0 (7)	N4—C9—C10—C11	178.3 (3)
Br4B—Cd1—Br4A—Br4C	140.1 (8)	C14—C9—C10—C11	−1.0 (6)
Br2—Cd1—Br4A—Br4B	−21.3 (4)	N4—C9—C10—N3	−0.2 (4)
Br1—Cd1—Br4A—Br4B	102.2 (4)	C14—C9—C10—N3	−179.4 (4)
Br3—Cd1—Br4A—Br4B	−140.1 (4)	C8—N3—C10—C9	0.6 (4)
Br4C—Cd1—Br4A—Br4B	−140.1 (8)	C8—N3—C10—C11	−177.7 (4)
Cd1—Br4A—Br4B—Br4C	93.9 (10)	C9—C10—C11—C12	0.1 (6)
Br4C—Br4A—Br4B—Cd1	−93.9 (10)	N3—C10—C11—C12	178.1 (4)
Br2—Cd1—Br4B—Br4A	160.2 (4)	C10—C11—C12—C13	0.8 (6)
Br1—Cd1—Br4B—Br4A	−84.7 (4)	C11—C12—C13—C14	−0.8 (6)
Br3—Cd1—Br4B—Br4A	45.3 (4)	C12—C13—C14—C9	−0.1 (6)
Br4C—Cd1—Br4B—Br4A	18.6 (5)	N4—C9—C14—C13	−178.1 (4)
Br4A—Cd1—Br4B—Br4C	−18.6 (5)	C10—C9—C14—C13	0.9 (6)
Br2—Cd1—Br4B—Br4C	141.6 (4)	C15—S1—C16—C17	−1.4 (4)
Br1—Cd1—Br4B—Br4C	−103.3 (4)	C15—S1—C16—C21	178.5 (3)
Br3—Cd1—Br4B—Br4C	26.7 (5)	C21—C16—C17—C18	0.0 (6)
Cd1—Br4A—Br4C—Br4B	−91.1 (9)	S1—C16—C17—C18	179.9 (3)
Br4B—Br4A—Br4C—Cd1	91.1 (9)	C16—C17—C18—C19	0.4 (6)
Cd1—Br4B—Br4C—Br4A	81.9 (10)	C17—C18—C19—C20	−0.6 (6)
Br4A—Br4B—Br4C—Cd1	−81.9 (10)	C17—C18—C19—C22	−178.8 (3)
Br2—Cd1—Br4C—Br4A	−67.1 (7)	C18—C19—C20—C21	0.3 (6)
Br1—Cd1—Br4C—Br4A	68.0 (7)	C22—C19—C20—C21	178.6 (4)
Br3—Cd1—Br4C—Br4A	−180.0 (7)	C19—C20—C21—C16	0.1 (6)
Br4B—Cd1—Br4C—Br4A	−22.6 (5)	C17—C16—C21—C20	−0.3 (6)
Br4A—Cd1—Br4C—Br4B	22.6 (5)	S1—C16—C21—C20	179.8 (3)
Br2—Cd1—Br4C—Br4B	−44.5 (5)	C28—N2—C22—N1	−0.6 (4)
Br1—Cd1—Br4C—Br4B	90.6 (4)	C28—N2—C22—C19	−179.7 (3)
Br3—Cd1—Br4C—Br4B	−157.4 (4)	C23—N1—C22—N2	0.8 (4)
C1—S2—C2—C3	1.6 (4)	C23—N1—C22—C19	179.9 (3)
C1—S2—C2—C7	−178.1 (3)	C18—C19—C22—N2	9.0 (6)
C7—C2—C3—C4	−0.6 (6)	C20—C19—C22—N2	−169.2 (4)
S2—C2—C3—C4	179.7 (3)	C18—C19—C22—N1	−169.9 (4)
C2—C3—C4—C5	1.0 (6)	C20—C19—C22—N1	11.8 (6)
C3—C4—C5—C6	−0.9 (6)	C22—N1—C23—C28	−0.7 (4)
C3—C4—C5—C8	178.5 (3)	C22—N1—C23—C24	179.1 (4)
C4—C5—C6—C7	0.4 (6)	C28—C23—C24—C25	0.4 (6)
C8—C5—C6—C7	−179.0 (4)	N1—C23—C24—C25	−179.4 (4)
C5—C6—C7—C2	0.0 (6)	C23—C24—C25—C26	−0.1 (6)
C3—C2—C7—C6	0.1 (6)	C24—C25—C26—C27	−0.2 (7)
S2—C2—C7—C6	179.8 (3)	C25—C26—C27—C28	0.1 (6)
C9—N4—C8—N3	0.6 (4)	N1—C23—C28—C27	179.3 (3)
C9—N4—C8—C5	−178.4 (4)	C24—C23—C28—C27	−0.5 (6)
C10—N3—C8—N4	−0.8 (4)	N1—C23—C28—N2	0.3 (4)
C10—N3—C8—C5	178.3 (3)	C24—C23—C28—N2	−179.5 (4)
C6—C5—C8—N4	179.6 (4)	C26—C27—C28—C23	0.2 (6)
C4—C5—C8—N4	0.2 (6)	C26—C27—C28—N2	178.9 (4)
C6—C5—C8—N3	0.8 (6)	C22—N2—C28—C23	0.2 (4)
C4—C5—C8—N3	−178.6 (4)	C22—N2—C28—C27	−178.7 (4)

Hydrogen-bond geometry (Å, º) top

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

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

Experimental details

Crystal data
Chemical formula	(C₁₄H₁₃N₂S)₂[CdBr₄]·C₂H₆O
M_r	960.76
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	123
a, b, c (Å)	22.1321 (15), 13.8746 (10), 22.2594 (16)
V (Å³)	6835.3 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	5.47
Crystal size (mm)	0.20 × 0.18 × 0.18

Data collection
Diffractometer	Bruker SMART APEX CCD detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.408, 0.439
No. of measured, independent and observed [I > 2σ(I)] reflections	93968, 7467, 5951
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.079, 0.79
No. of reflections	7467
No. of parameters	407
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
	w = 1/[σ²(F_o²) + (0.0318P)² + 49.2262P] where P = (F_o² + 2F_c²)/3
Δρ_max, Δρ_min (e Å⁻³)	0.87, −0.69

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and CAMERON (Watkin et al., 1996), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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	0.950	2.554	3.464 (8)	160

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

Acknowledgements

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.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker. (1998). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Huang, W. & Scarborough, R. M. (1999). Tetrahedron Lett. 40, 2665–2668. Web of Science CrossRef CAS Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Preston, P. N. (1974). Chem. Rev. 74, 279–314. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England. Google Scholar
Zarrinmayeh, H., Nunes, A. M., Ornstein, P. L., Zimmerman, D. M., Arnold, M. B., Schober, D. A., Gackenheimer, S. L., Bruns, R. F., Hipskind, P. A., Britton, T. C., Cantrell, B. E. & Gehlert, D. R. (1998). J. Med. Chem. 41, 2709–2719. Web of Science CSD CrossRef CAS PubMed Google Scholar
Zhu, Z., Lippa, B., Drach, J. C. & Townsend, L. B. (2000). J. Med. Chem. 43, 2430–2437. Web of Science CrossRef PubMed CAS Google Scholar
Ziaulla, M., Manjunatha, M. N., Sankolli, R., Nagasundara, K. R. & Begum, N. S. (2011). Acta Cryst. E67, o341–o342. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page m771

doi:10.1107/S1600536811018058

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

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