1-Benzyl-3-[(trimethyl-sil-yl)meth-yl]benzimidazolium chloride monohydrate.

The title compound, C(18)H(23)N(2)Si(+)·Cl(-)·H(2)O, was synthesized from 1-[(trimethyl-sil-yl)meth-yl]benzimidazole and benzyl chloride in dimethyl-formamide. The benzimidazole ring system is approximately planar, with a maximum deviation of 0.022 (2) Å, and makes an angle of 74.80 (12)° with the phenyl ring. The crystal packing is stabilized by O-H⋯Cl, C-H⋯Cl, C-H⋯O and C-H⋯π inter-actions between symmetry-related mol-ecules together with π-π stacking inter-actions between the imidazolium and benzene rings [centroid-centroid distance = 3.5690 (15) Å] and between the benzene rings [centroid-centroid distance = 3.7223 (14) Å].

Related literature

For general background to benzimidazole compounds and for the biological activity of related structures, see: Galal et al. (2009 ▶); Huang et al. (2006 ▶); Küçükbay & Durmaz (1997 ▶); Küçükbay et al. (1995 ▶, 2003 ▶, 2004 ▶, 2010 ▶); Lukevics et al. (2001 ▶); Singh & Lown (2000 ▶); Tavman et al. (2005 ▶); Turner & Denny (1996 ▶); Williams et al. (2002 ▶); Yılmaz & Küçükbay (2009 ▶); Çetinkaya et al. (1996 ▶). For similar structures, see: Akkurt et al. (2008 ▶, 2010 ▶).

Experimental

Crystal data

C18H23N2Si+·Cl−·H2O

M = 348.94

Triclinic,

a = 9.3592 (7) Å

b = 10.9500 (9) Å

c = 11.0522 (8) Å

α = 117.594 (6)°

β = 103.295 (6)°

γ = 92.094 (6)°

V = 963.39 (15) Å3

Z = 2

Mo Kα radiation

μ = 0.27 mm−1

T = 296 K

0.57 × 0.50 × 0.36 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.859, T max = 0.909

12149 measured reflections

3987 independent reflections

3241 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.135

S = 1.07

3987 reflections

211 parameters

H-atom parameters constrained

Δρmax = 0.32 e Å−3

Δρmin = −0.32 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), 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/S1600536810024128/dn2582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024128/dn2582Isup2.hkl

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

C18H23N2Si+·Cl−·H2O	Z = 2
Mr = 348.94	F(000) = 372
Triclinic, P1	Dx = 1.203 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3592 (7) Å	Cell parameters from 28124 reflections
b = 10.9500 (9) Å	θ = 2.1–28.0°
c = 11.0522 (8) Å	µ = 0.27 mm−1
α = 117.594 (6)°	T = 296 K
β = 103.295 (6)°	Prism, colourless
γ = 92.094 (6)°	0.57 × 0.50 × 0.36 mm
V = 963.39 (15) Å3

Stoe IPDS 2 diffractometer	3987 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3241 reflections with I > 2σ(I)
plane graphite	Rint = 0.029
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.1°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −13→12
Tmin = 0.859, Tmax = 0.909	l = −13→13
12149 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) = 0.135	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0637P)2 + 0.2683P] where P = (Fo2 + 2Fc2)/3
3987 reflections	(Δ/σ)max < 0.001
211 parameters	Δρmax = 0.32 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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	0.53328 (7)	0.20172 (7)	0.79168 (6)	0.05705 (19)
N1	0.72385 (17)	0.36741 (17)	0.52896 (17)	0.0466 (4)
N2	0.59349 (17)	0.36730 (17)	0.66907 (17)	0.0466 (4)
C1	0.4923 (2)	0.33506 (19)	0.54087 (19)	0.0428 (4)
C2	0.3377 (2)	0.3101 (2)	0.4971 (2)	0.0521 (5)
H2	0.2816	0.3104	0.5566	0.063*
C3	0.2721 (2)	0.2847 (2)	0.3611 (2)	0.0587 (5)
H3	0.1688	0.2667	0.3276	0.070*
C4	0.3560 (2)	0.2853 (3)	0.2717 (2)	0.0592 (5)
H4	0.3071	0.2682	0.1806	0.071*
C5	0.5084 (2)	0.3104 (2)	0.3150 (2)	0.0532 (5)
H5	0.5641	0.3111	0.2555	0.064*
C6	0.57570 (19)	0.33479 (19)	0.4512 (2)	0.0432 (4)
C7	0.7293 (2)	0.3855 (2)	0.6574 (2)	0.0505 (5)
H7	0.8165	0.4079	0.7293	0.061*
C8	0.8534 (2)	0.3833 (2)	0.4794 (2)	0.0547 (5)
H8A	0.9413	0.4273	0.5602	0.066*
H8B	0.8371	0.4442	0.4377	0.066*
C9	0.8803 (2)	0.2461 (2)	0.3720 (2)	0.0510 (5)
C10	0.8520 (3)	0.2111 (3)	0.2308 (3)	0.0717 (7)
H10	0.8171	0.2741	0.2014	0.086*
C11	0.8748 (3)	0.0831 (4)	0.1329 (3)	0.0935 (10)
H11	0.8546	0.0600	0.0377	0.112*
C12	0.9272 (3)	−0.0100 (3)	0.1753 (4)	0.0947 (10)
H12	0.9404	−0.0970	0.1089	0.114*
C13	0.9600 (3)	0.0255 (3)	0.3158 (4)	0.0909 (10)
H13	0.9980	−0.0367	0.3451	0.109*
C14	0.9372 (3)	0.1527 (3)	0.4141 (3)	0.0700 (7)
H14	0.9602	0.1760	0.5095	0.084*
C15	0.5549 (3)	0.3754 (2)	0.7947 (2)	0.0549 (5)
H15A	0.4625	0.4122	0.8003	0.066*
H15B	0.6320	0.4406	0.8796	0.066*
C16	0.3837 (3)	0.0757 (3)	0.6328 (3)	0.0812 (8)
H16A	0.4063	0.0662	0.5487	0.122*
H16B	0.2907	0.1090	0.6377	0.122*
H16C	0.3767	−0.0135	0.6297	0.122*
C17	0.4849 (4)	0.2374 (4)	0.9569 (3)	0.1001 (10)
H17A	0.4744	0.1524	0.9619	0.150*
H17B	0.3928	0.2732	0.9569	0.150*
H17C	0.5624	0.3050	1.0376	0.150*
C18	0.7121 (3)	0.1391 (3)	0.7877 (3)	0.0899 (9)
H18A	0.7028	0.0478	0.7796	0.135*
H18B	0.7869	0.2023	0.8737	0.135*
H18C	0.7403	0.1344	0.7076	0.135*
O1	0.9113 (3)	0.6314 (2)	0.9603 (2)	0.1024 (7)
H1A	0.9910	0.6000	0.9420	0.154*
H1B	0.9090	0.6350	1.0380	0.154*
Cl1	1.14370 (9)	0.44812 (10)	0.80296 (8)	0.0961 (3)

	U11	U22	U33	U12	U13	U23
Si1	0.0616 (4)	0.0668 (4)	0.0477 (3)	0.0106 (3)	0.0191 (3)	0.0301 (3)
N1	0.0349 (8)	0.0565 (9)	0.0533 (9)	0.0048 (7)	0.0145 (7)	0.0295 (8)
N2	0.0448 (9)	0.0524 (9)	0.0460 (8)	0.0074 (7)	0.0162 (7)	0.0251 (7)
C1	0.0401 (9)	0.0458 (9)	0.0466 (9)	0.0086 (7)	0.0162 (8)	0.0238 (8)
C2	0.0404 (10)	0.0611 (12)	0.0632 (12)	0.0110 (9)	0.0240 (9)	0.0324 (10)
C3	0.0358 (10)	0.0717 (14)	0.0673 (13)	0.0081 (9)	0.0120 (9)	0.0339 (11)
C4	0.0471 (12)	0.0770 (14)	0.0527 (11)	0.0088 (10)	0.0087 (9)	0.0333 (11)
C5	0.0486 (11)	0.0686 (13)	0.0516 (11)	0.0106 (9)	0.0193 (9)	0.0340 (10)
C6	0.0343 (9)	0.0484 (10)	0.0507 (10)	0.0068 (7)	0.0145 (8)	0.0260 (8)
C7	0.0418 (10)	0.0554 (11)	0.0511 (11)	0.0031 (8)	0.0079 (8)	0.0260 (9)
C8	0.0360 (10)	0.0667 (13)	0.0736 (13)	0.0050 (9)	0.0216 (9)	0.0412 (11)
C9	0.0311 (9)	0.0671 (12)	0.0673 (12)	0.0090 (8)	0.0197 (9)	0.0400 (10)
C10	0.0529 (13)	0.1023 (19)	0.0737 (15)	0.0312 (13)	0.0236 (12)	0.0498 (15)
C11	0.0647 (17)	0.126 (3)	0.0702 (17)	0.0308 (17)	0.0212 (14)	0.0299 (17)
C12	0.0684 (18)	0.0793 (19)	0.120 (3)	0.0195 (15)	0.0432 (18)	0.0266 (18)
C13	0.087 (2)	0.088 (2)	0.146 (3)	0.0402 (16)	0.069 (2)	0.077 (2)
C14	0.0671 (15)	0.0864 (17)	0.0943 (18)	0.0279 (13)	0.0444 (14)	0.0631 (15)
C15	0.0599 (12)	0.0622 (12)	0.0420 (10)	0.0129 (10)	0.0203 (9)	0.0217 (9)
C16	0.0781 (18)	0.0771 (17)	0.0790 (17)	−0.0077 (13)	0.0151 (14)	0.0347 (14)
C17	0.142 (3)	0.111 (2)	0.0703 (17)	0.022 (2)	0.0513 (19)	0.0526 (17)
C18	0.0818 (19)	0.093 (2)	0.088 (2)	0.0247 (16)	0.0135 (16)	0.0423 (17)
O1	0.1114 (17)	0.0974 (15)	0.0822 (13)	0.0288 (13)	0.0144 (12)	0.0355 (12)
Cl1	0.0818 (5)	0.1278 (7)	0.0780 (5)	0.0348 (4)	0.0259 (4)	0.0465 (4)

Si1—C18	1.834 (3)	C9—C10	1.378 (3)
Si1—C17	1.850 (3)	C9—C14	1.383 (3)
Si1—C16	1.852 (3)	C10—C11	1.380 (4)
Si1—C15	1.890 (2)	C10—H10	0.9300
N1—C7	1.328 (3)	C11—C12	1.368 (5)
N1—C6	1.386 (2)	C11—H11	0.9300
N1—C8	1.476 (2)	C12—C13	1.367 (5)
N2—C7	1.324 (2)	C12—H12	0.9300
N2—C1	1.387 (2)	C13—C14	1.376 (4)
N2—C15	1.478 (2)	C13—H13	0.9300
C1—C2	1.389 (3)	C14—H14	0.9300
C1—C6	1.394 (2)	C15—H15A	0.9700
C2—C3	1.374 (3)	C15—H15B	0.9700
C2—H2	0.9300	C16—H16A	0.9600
C3—C4	1.398 (3)	C16—H16B	0.9600
C3—H3	0.9300	C16—H16C	0.9600
C4—C5	1.369 (3)	C17—H17A	0.9600
C4—H4	0.9300	C17—H17B	0.9600
C5—C6	1.384 (3)	C17—H17C	0.9600
C5—H5	0.9300	C18—H18A	0.9600
C7—H7	0.9300	C18—H18B	0.9600
C8—C9	1.497 (3)	C18—H18C	0.9600
C8—H8A	0.9700	O1—H1A	0.8598
C8—H8B	0.9700	O1—H1B	0.8466
C18—Si1—C17	111.82 (16)	C14—C9—C8	120.0 (2)
C18—Si1—C16	110.58 (15)	C9—C10—C11	120.5 (3)
C17—Si1—C16	110.93 (16)	C9—C10—H10	119.8
C18—Si1—C15	107.44 (14)	C11—C10—H10	119.8
C17—Si1—C15	105.86 (13)	C12—C11—C10	120.2 (3)
C16—Si1—C15	110.04 (12)	C12—C11—H11	119.9
C7—N1—C6	108.20 (15)	C10—C11—H11	119.9
C7—N1—C8	125.70 (17)	C13—C12—C11	119.7 (3)
C6—N1—C8	126.08 (16)	C13—C12—H12	120.1
C7—N2—C1	108.16 (15)	C11—C12—H12	120.1
C7—N2—C15	126.39 (17)	C12—C13—C14	120.4 (3)
C1—N2—C15	125.43 (16)	C12—C13—H13	119.8
N2—C1—C2	131.97 (17)	C14—C13—H13	119.8
N2—C1—C6	106.56 (16)	C13—C14—C9	120.4 (3)
C2—C1—C6	121.45 (18)	C13—C14—H14	119.8
C3—C2—C1	116.40 (18)	C9—C14—H14	119.8
C3—C2—H2	121.8	N2—C15—Si1	113.64 (13)
C1—C2—H2	121.8	N2—C15—H15A	108.8
C2—C3—C4	122.03 (19)	Si1—C15—H15A	108.8
C2—C3—H3	119.0	N2—C15—H15B	108.8
C4—C3—H3	119.0	Si1—C15—H15B	108.8
C5—C4—C3	121.6 (2)	H15A—C15—H15B	107.7
C5—C4—H4	119.2	Si1—C16—H16A	109.5
C3—C4—H4	119.2	Si1—C16—H16B	109.5
C4—C5—C6	116.92 (18)	H16A—C16—H16B	109.5
C4—C5—H5	121.5	Si1—C16—H16C	109.5
C6—C5—H5	121.5	H16A—C16—H16C	109.5
C5—C6—N1	131.92 (17)	H16B—C16—H16C	109.5
C5—C6—C1	121.62 (17)	Si1—C17—H17A	109.5
N1—C6—C1	106.41 (16)	Si1—C17—H17B	109.5
N2—C7—N1	110.68 (17)	H17A—C17—H17B	109.5
N2—C7—H7	124.7	Si1—C17—H17C	109.5
N1—C7—H7	124.7	H17A—C17—H17C	109.5
N1—C8—C9	112.22 (16)	H17B—C17—H17C	109.5
N1—C8—H8A	109.2	Si1—C18—H18A	109.5
C9—C8—H8A	109.2	Si1—C18—H18B	109.5
N1—C8—H8B	109.2	H18A—C18—H18B	109.5
C9—C8—H8B	109.2	Si1—C18—H18C	109.5
H8A—C8—H8B	107.9	H18A—C18—H18C	109.5
C10—C9—C14	118.7 (2)	H18B—C18—H18C	109.5
C10—C9—C8	121.3 (2)	H1A—O1—H1B	107.0
C7—N2—C1—C2	−178.0 (2)	C15—N2—C7—N1	178.44 (17)
C15—N2—C1—C2	3.6 (3)	C6—N1—C7—N2	−0.3 (2)
C7—N2—C1—C6	0.1 (2)	C8—N1—C7—N2	178.18 (18)
C15—N2—C1—C6	−178.27 (17)	C7—N1—C8—C9	109.6 (2)
N2—C1—C2—C3	178.1 (2)	C6—N1—C8—C9	−72.2 (2)
C6—C1—C2—C3	0.2 (3)	N1—C8—C9—C10	108.7 (2)
C1—C2—C3—C4	−0.6 (3)	N1—C8—C9—C14	−72.5 (2)
C2—C3—C4—C5	0.4 (4)	C14—C9—C10—C11	2.3 (4)
C3—C4—C5—C6	0.2 (3)	C8—C9—C10—C11	−178.8 (2)
C4—C5—C6—N1	−177.7 (2)	C9—C10—C11—C12	−0.5 (4)
C4—C5—C6—C1	−0.6 (3)	C10—C11—C12—C13	−1.5 (5)
C7—N1—C6—C5	177.7 (2)	C11—C12—C13—C14	1.7 (5)
C8—N1—C6—C5	−0.7 (3)	C12—C13—C14—C9	0.2 (4)
C7—N1—C6—C1	0.3 (2)	C10—C9—C14—C13	−2.2 (3)
C8—N1—C6—C1	−178.13 (17)	C8—C9—C14—C13	179.0 (2)
N2—C1—C6—C5	−177.97 (18)	C7—N2—C15—Si1	−91.7 (2)
C2—C1—C6—C5	0.4 (3)	C1—N2—C15—Si1	86.4 (2)
N2—C1—C6—N1	−0.2 (2)	C18—Si1—C15—N2	60.61 (19)
C2—C1—C6—N1	178.10 (18)	C17—Si1—C15—N2	−179.77 (18)
C1—N2—C7—N1	0.1 (2)	C16—Si1—C15—N2	−59.84 (19)

Cg3 is the centroid of the C9–C14 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Cl1	0.86	2.45	3.257 (2)	157
O1—H1B···Cl1i	0.85	2.45	3.250 (3)	158
C7—H7···O1	0.93	2.51	3.170 (3)	128
C8—H8A···Cl1	0.97	2.81	3.703 (2)	153
C3—H3···Cg3ii	0.93	2.69	3.526 (2)	151

	Centroid–centroid	plane–plane	offset
Cg1···Cg2i	3.5690 (15)	3.430 (1)	16.0
Cg2···Cg2i	3.7223 (14)	3.446 (1)	22.2

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C9–C14 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Cl1	0.86	2.45	3.257 (2)	157
O1—H1B⋯Cl1i	0.85	2.45	3.250 (3)	158
C7—H7⋯O1	0.93	2.51	3.170 (3)	128
C8—H8A⋯Cl1	0.97	2.81	3.703 (2)	153
C3—H3⋯Cg3ii	0.93	2.69	3.526 (2)	151

Symmetry codes: (i) ; (ii) .