1-(Prop-2-en-1-yl)-3-[(trimethyl-sil-yl)meth-yl]benzimidazolium bromide monohydrate.

In the title compound, C(14)H(21)N(2)Si(+)·Br(-)·H(2)O, the benzimidazole ring system is almost planar [maximum deviation = 0.021 (2) Å]. In the crystal, O-H⋯Br and C-H⋯O hydrogen bonds link the ions via the O atoms of the water mol-ecules. In addition, there are π-π stacking inter-actions between the centroids of the benzene and imidazole rings of the benzimidazole ring system [centroid-centroid distances = 3.521 (3) and 3.575 (2) Å].

Related literature

For the anti­tumour activity of alkyl­silyl-substituted benzimidazole derivatives, see: Kleemann et al. (2009 ▶); Lukevics et al. (2001 ▶); Ignatovich et al. (2010 ▶). For the pharmacological activity of benzimidazole compounds, see: Singh & Lown (2000 ▶); Huang et al. (2006 ▶); Turner & Denny (1996 ▶); Galal et al. (2009 ▶); Küçükbay et al. (2003 ▶, 2004 ▶, 2009 ▶, 2010a ▶,b ▶); Şireci et al. (2010 ▶); Yılmaz & Küçükbay (2009 ▶); Yılmaz et al. (2010 ▶). For the structures of similar benzimidazole derivatives, see: Akkurt et al. (2008 ▶, 2010a ▶,b ▶); Yıldırım et al. (2006 ▶). For π–π inter­actions, see: Janiak (2000 ▶).

Experimental

Crystal data

C14H21N2Si+·Br−·H2O

M = 343.33

Triclinic,

a = 8.9063 (2) Å

b = 10.4720 (2) Å

c = 10.9439 (3) Å

α = 66.542 (4)°

β = 71.479 (4)°

γ = 80.625 (5)°

V = 887.07 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.38 mm−1

T = 294 K

0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T min = 0.647, T max = 0.647

18957 measured reflections

3618 independent reflections

2202 reflections with I > 2σ(I)

R int = 0.073

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.121

S = 1.02

3618 reflections

175 parameters

3 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.35 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033015/dn2597sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033015/dn2597Isup2.hkl

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

C14H21N2Si+·Br−·H2O	Z = 2
Mr = 343.33	F(000) = 356
Triclinic, P1	Dx = 1.285 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9063 (2) Å	Cell parameters from 3185 reflections
b = 10.4720 (2) Å	θ = 2.4–26.4°
c = 10.9439 (3) Å	µ = 2.38 mm−1
α = 66.542 (4)°	T = 294 K
β = 71.479 (4)°	Block, white
γ = 80.625 (5)°	0.20 × 0.20 × 0.20 mm
V = 887.07 (5) Å3

Rigaku R-AXIS RAPID-S diffractometer	3618 independent reflections
Radiation source: Sealed Tube	2202 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.073
Detector resolution: 10.0000 pixels mm-1	θmax = 26.4°, θmin = 2.4°
dtprofit.ref scans	h = −11→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −13→13
Tmin = 0.647, Tmax = 0.647	l = −13→13
18957 measured reflections

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0356P)2 + 0.3659P] where P = (Fo2 + 2Fc2)/3
3618 reflections	(Δ/σ)max = 0.006
175 parameters	Δρmax = 0.30 e Å−3
3 restraints	Δρmin = −0.35 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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
Si1	0.53721 (14)	0.18235 (12)	0.70600 (11)	0.0684 (3)
N1	0.6155 (3)	0.3381 (3)	0.8362 (3)	0.0570 (7)
N2	0.7515 (3)	0.3069 (3)	0.9818 (3)	0.0624 (8)
C1	0.5921 (4)	0.3128 (4)	1.0536 (4)	0.0562 (9)
C2	0.5185 (5)	0.3059 (4)	1.1879 (4)	0.0669 (10)
H2	0.5760	0.2927	1.2499	0.080*
C3	0.3555 (5)	0.3197 (4)	1.2249 (4)	0.0722 (11)
H3	0.3016	0.3143	1.3147	0.087*
C4	0.2689 (5)	0.3415 (4)	1.1314 (4)	0.0673 (10)
H4	0.1590	0.3509	1.1604	0.081*
C5	0.3419 (4)	0.3495 (4)	0.9978 (4)	0.0625 (9)
H5	0.2844	0.3649	0.9353	0.075*
C6	0.5059 (4)	0.3332 (4)	0.9609 (3)	0.0546 (8)
C7	0.7597 (4)	0.3221 (4)	0.8533 (4)	0.0634 (10)
H7	0.8535	0.3216	0.7846	0.076*
C8	0.5773 (5)	0.3529 (4)	0.7092 (3)	0.0634 (10)
H8A	0.6649	0.3954	0.6294	0.076*
H8B	0.4847	0.4153	0.7007	0.076*
C9	0.7201 (6)	0.0716 (5)	0.7079 (6)	0.1093 (17)
H9A	0.7050	−0.0136	0.7007	0.164*
H9B	0.7453	0.0508	0.7931	0.164*
H9C	0.8055	0.1197	0.6310	0.164*
C10	0.4835 (6)	0.2278 (6)	0.5440 (5)	0.1070 (17)
H10A	0.3868	0.2840	0.5472	0.160*
H10B	0.4690	0.1442	0.5337	0.160*
H10C	0.5666	0.2790	0.4667	0.160*
C11	0.3721 (6)	0.0963 (5)	0.8586 (5)	0.1049 (16)
H11A	0.3672	0.0022	0.8668	0.157*
H11B	0.2741	0.1463	0.8470	0.157*
H11C	0.3897	0.0958	0.9409	0.157*
C12	0.8871 (5)	0.2883 (5)	1.0387 (4)	0.0781 (12)
H12A	0.8701	0.3488	1.0902	0.094*
H12B	0.9831	0.3152	0.9629	0.094*
C13	0.9078 (5)	0.1417 (5)	1.1316 (6)	0.0889 (14)
H13	0.9301	0.0731	1.0937	0.107*
C14	0.8967 (6)	0.1037 (6)	1.2611 (7)	0.1190 (19)
H14A	0.8744	0.1698	1.3021	0.143*
H14B	0.9109	0.0101	1.3139	0.143*
O1W	1.0389 (5)	0.3039 (4)	0.5704 (4)	0.1283 (12)
H1W	1.0104	0.3435	0.4962	0.192*
H2W	1.0969	0.3573	0.5761	0.192*
Br1	0.85464 (5)	0.48204 (5)	0.31301 (5)	0.0895 (2)

	U11	U22	U33	U12	U13	U23
Si1	0.0770 (8)	0.0756 (7)	0.0588 (6)	−0.0017 (6)	−0.0259 (6)	−0.0264 (6)
N1	0.0539 (18)	0.067 (2)	0.0517 (17)	−0.0005 (14)	−0.0141 (14)	−0.0253 (15)
N2	0.0522 (18)	0.076 (2)	0.065 (2)	−0.0021 (15)	−0.0165 (15)	−0.0321 (17)
C1	0.052 (2)	0.064 (2)	0.055 (2)	−0.0033 (17)	−0.0155 (17)	−0.0241 (18)
C2	0.071 (3)	0.080 (3)	0.055 (2)	−0.005 (2)	−0.018 (2)	−0.029 (2)
C3	0.072 (3)	0.082 (3)	0.059 (2)	−0.007 (2)	−0.005 (2)	−0.030 (2)
C4	0.054 (2)	0.073 (3)	0.072 (3)	−0.0029 (19)	−0.008 (2)	−0.031 (2)
C5	0.055 (2)	0.066 (2)	0.066 (2)	0.0009 (18)	−0.0174 (19)	−0.0259 (19)
C6	0.052 (2)	0.061 (2)	0.053 (2)	−0.0012 (16)	−0.0122 (17)	−0.0258 (17)
C7	0.053 (2)	0.076 (3)	0.062 (2)	−0.0019 (18)	−0.0085 (18)	−0.032 (2)
C8	0.069 (2)	0.072 (3)	0.045 (2)	−0.0009 (19)	−0.0158 (18)	−0.0188 (18)
C9	0.107 (4)	0.087 (3)	0.137 (5)	0.015 (3)	−0.043 (3)	−0.044 (3)
C10	0.121 (4)	0.144 (5)	0.079 (3)	−0.010 (3)	−0.041 (3)	−0.053 (3)
C11	0.120 (4)	0.103 (4)	0.090 (3)	−0.039 (3)	−0.011 (3)	−0.035 (3)
C12	0.056 (2)	0.107 (4)	0.085 (3)	−0.005 (2)	−0.027 (2)	−0.042 (3)
C13	0.067 (3)	0.099 (4)	0.115 (4)	0.009 (2)	−0.044 (3)	−0.044 (3)
C14	0.098 (4)	0.117 (5)	0.130 (5)	0.009 (3)	−0.055 (4)	−0.022 (4)
O1W	0.124 (3)	0.130 (3)	0.132 (3)	−0.002 (2)	−0.047 (2)	−0.042 (2)
Br1	0.0699 (3)	0.1215 (4)	0.0769 (3)	0.0007 (3)	−0.0195 (2)	−0.0391 (3)

Si1—C9	1.840 (5)	C8—H8A	0.9700
Si1—C10	1.842 (4)	C8—H8B	0.9700
Si1—C11	1.854 (5)	C9—H9A	0.9600
Si1—C8	1.893 (4)	C9—H9B	0.9600
N1—C7	1.329 (4)	C9—H9C	0.9600
N1—C6	1.390 (4)	C10—H10A	0.9600
N1—C8	1.478 (4)	C10—H10B	0.9600
N2—C7	1.330 (4)	C10—H10C	0.9600
N2—C1	1.392 (4)	C11—H11A	0.9600
N2—C12	1.480 (5)	C11—H11B	0.9600
C1—C2	1.383 (5)	C11—H11C	0.9600
C1—C6	1.390 (5)	C12—C13	1.486 (6)
C2—C3	1.377 (5)	C12—H12A	0.9700
C2—H2	0.9300	C12—H12B	0.9700
C3—C4	1.397 (5)	C13—C14	1.285 (7)
C3—H3	0.9300	C13—H13	0.9300
C4—C5	1.372 (5)	C14—H14A	0.9300
C4—H4	0.9300	C14—H14B	0.9300
C5—C6	1.387 (5)	O1W—H1W	0.8512
C5—H5	0.9300	O1W—H2W	0.8513
C7—H7	0.9300
C9—Si1—C10	111.7 (2)	Si1—C8—H8A	108.8
C9—Si1—C11	110.6 (2)	N1—C8—H8B	108.8
C10—Si1—C11	110.6 (2)	Si1—C8—H8B	108.8
C9—Si1—C8	107.8 (2)	H8A—C8—H8B	107.7
C10—Si1—C8	105.9 (2)	Si1—C9—H9A	109.5
C11—Si1—C8	110.15 (19)	Si1—C9—H9B	109.5
C7—N1—C6	108.0 (3)	H9A—C9—H9B	109.5
C7—N1—C8	126.3 (3)	Si1—C9—H9C	109.5
C6—N1—C8	125.7 (3)	H9A—C9—H9C	109.5
C7—N2—C1	107.9 (3)	H9B—C9—H9C	109.5
C7—N2—C12	126.3 (3)	Si1—C10—H10A	109.5
C1—N2—C12	125.8 (3)	Si1—C10—H10B	109.5
C2—C1—C6	121.7 (3)	H10A—C10—H10B	109.5
C2—C1—N2	131.6 (3)	Si1—C10—H10C	109.5
C6—C1—N2	106.7 (3)	H10A—C10—H10C	109.5
C3—C2—C1	116.5 (3)	H10B—C10—H10C	109.5
C3—C2—H2	121.8	Si1—C11—H11A	109.5
C1—C2—H2	121.8	Si1—C11—H11B	109.5
C2—C3—C4	121.9 (4)	H11A—C11—H11B	109.5
C2—C3—H3	119.0	Si1—C11—H11C	109.5
C4—C3—H3	119.0	H11A—C11—H11C	109.5
C5—C4—C3	121.7 (4)	H11B—C11—H11C	109.5
C5—C4—H4	119.2	N2—C12—C13	111.7 (3)
C3—C4—H4	119.2	N2—C12—H12A	109.3
C4—C5—C6	116.6 (3)	C13—C12—H12A	109.3
C4—C5—H5	121.7	N2—C12—H12B	109.3
C6—C5—H5	121.7	C13—C12—H12B	109.3
C5—C6—N1	131.6 (3)	H12A—C12—H12B	107.9
C5—C6—C1	121.7 (3)	C14—C13—C12	124.1 (5)
N1—C6—C1	106.7 (3)	C14—C13—H13	118.0
N2—C7—N1	110.8 (3)	C12—C13—H13	118.0
N2—C7—H7	124.6	C13—C14—H14A	120.0
N1—C7—H7	124.6	C13—C14—H14B	120.0
N1—C8—Si1	113.9 (2)	H14A—C14—H14B	120.0
N1—C8—H8A	108.8	H1W—O1W—H2W	109.9

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1W	0.93	2.46	3.351 (5)	161.
O1W—H1W···Br1	0.85	2.62	3.445 (4)	165.
O1W—H2W···Br1i	0.85	2.59	3.360 (4)	152.

ring 1/ring 2	ccd	ipd	sa
Cg1->Cg2ii	3.521 (3)	3.386	15.9
Cg2->Cg2ii	3.575 (2)	3.396	18.2

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1W	0.93	2.46	3.351 (5)	161
O1W—H1W⋯Br1	0.85	2.62	3.445 (4)	165
O1W—H2W⋯Br1i	0.85	2.59	3.360 (4)	152

Symmetry code: (i) .