1-{[Dimeth-yl(phen-yl)sil-yl]meth-yl}-3-(2-phenyl-eth-yl)-1H-benzimidazol-3-ium bromide monohydrate.

The title compound, C(24)H(27)N(2)Si(+)·Br(-)·H(2)O, was synthesized from 1-(dimethyl-phenyl-silylmeth-yl)-1H-benzimidazole and (2-bromo-eth-yl)benzene in dimethyl-formamide. The benzimidazole ring system is nearly planar, with a maximum deviation of 0.015 (5) Å, and forms dihedral angles of 73.0 (3) and 39.6 (2)°, with the phenyl rings. In the crystal, mol-ecules are linked by O-H⋯Br, C-H⋯Br and C-H⋯O hydrogen bonds. In addition, the structure features π-π stacking inter-actions, with a face-to-face separation of 3.644 (3) Å between parallel benzimidazole ring systems.

Related literature

For general background to benzimidazole derivatives, see: Lukevics et al. (2001 ▶); Tavman et al. (2005 ▶); Küçükbay et al. (1995 ▶, 2004 ▶, 2010 ▶, 2011 ▶); Yılmaz et al. (2011 ▶); Çetinkaya et al. (1996 ▶). For similar structures, see: Akkurt et al. (2010a ▶,b ▶); Baktır et al. (2010 ▶).

Experimental

Crystal data

C24H27N2Si+·Br−·H2O

M = 469.48

Monoclinic,

a = 15.1750 (11) Å

b = 8.9097 (6) Å

c = 17.9440 (14) Å

β = 96.235 (6)°

V = 2411.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.77 mm−1

T = 296 K

0.26 × 0.20 × 0.13 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.656, T max = 0.803

19519 measured reflections

5536 independent reflections

3023 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.173

S = 1.03

5536 reflections

244 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.82 e Å−3

Δρmin = −0.53 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812034915/nr2031sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034915/nr2031Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034915/nr2031Isup3.cml

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

C24H27N2Si+·Br−·H2O	F(000) = 976
Mr = 469.48	Dx = 1.293 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 16623 reflections
a = 15.1750 (11) Å	θ = 1.9–28.0°
b = 8.9097 (6) Å	µ = 1.77 mm−1
c = 17.9440 (14) Å	T = 296 K
β = 96.235 (6)°	Prism, colourless
V = 2411.8 (3) Å3	0.26 × 0.20 × 0.13 mm
Z = 4

Stoe IPDS 2 diffractometer	5536 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3023 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.074
Detector resolution: 6.67 pixels mm-1	θmax = 27.7°, θmin = 2.3°
ω scans	h = −19→19
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→11
Tmin = 0.656, Tmax = 0.803	l = −23→22
19519 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0795P)2 + 0.0123P] where P = (Fo2 + 2Fc2)/3
5536 reflections	(Δ/σ)max < 0.001
244 parameters	Δρmax = 0.82 e Å−3
3 restraints	Δρmin = −0.53 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	0.78140 (10)	0.80539 (15)	0.01520 (8)	0.0622 (5)
N1	0.6284 (2)	0.4424 (4)	0.1286 (2)	0.0494 (11)
N2	0.6390 (2)	0.6253 (4)	0.0489 (2)	0.0504 (11)
C1	0.6113 (3)	0.3800 (5)	0.0576 (3)	0.0485 (14)
C2	0.5887 (3)	0.2349 (5)	0.0337 (3)	0.0615 (19)
C3	0.5739 (4)	0.2140 (6)	−0.0423 (3)	0.071 (2)
C4	0.5800 (4)	0.3300 (6)	−0.0928 (3)	0.0676 (19)
C5	0.6016 (3)	0.4728 (6)	−0.0695 (3)	0.0598 (17)
C6	0.6175 (3)	0.4968 (5)	0.0065 (3)	0.0479 (14)
C7	0.6444 (3)	0.5879 (5)	0.1201 (3)	0.0550 (17)
C8	0.6288 (3)	0.3604 (6)	0.1995 (3)	0.0611 (17)
C9	0.7112 (3)	0.3908 (4)	0.2537 (2)	0.092 (3)
C10	0.7978 (3)	0.3669 (4)	0.2238 (2)	0.0805 (14)
C11	0.8658 (3)	0.4673 (4)	0.2459 (2)	0.0805 (14)
C12	0.9508 (5)	0.4492 (9)	0.2211 (5)	0.103 (3)
C13	0.9606 (5)	0.3318 (9)	0.1751 (5)	0.104 (3)
C14	0.8930 (5)	0.2323 (9)	0.1538 (5)	0.105 (3)
C15	0.8145 (5)	0.2532 (7)	0.1779 (3)	0.0805 (14)
C16	0.6585 (3)	0.7756 (5)	0.0205 (3)	0.0600 (16)
C17	0.8383 (5)	0.8082 (7)	0.1119 (3)	0.088 (3)
C18	0.7921 (2)	0.9879 (4)	−0.03326 (19)	0.090 (3)
C19	0.8198 (2)	0.6457 (4)	−0.03916 (19)	0.0629 (17)
C20	0.7951 (2)	0.6338 (4)	−0.11654 (19)	0.073 (2)
C21	0.8174 (4)	0.5106 (8)	−0.1566 (4)	0.087 (3)
C22	0.8647 (5)	0.3947 (8)	−0.1216 (4)	0.093 (3)
C23	0.8905 (5)	0.4028 (7)	−0.0465 (5)	0.102 (3)
C24	0.8673 (4)	0.5258 (7)	−0.0051 (4)	0.085 (3)
Br1	0.59570 (4)	0.93585 (6)	0.20869 (3)	0.0720 (2)
OW1	0.5856 (3)	0.6540 (5)	0.3323 (3)	0.0960 (19)
H2	0.58390	0.15670	0.06740	0.0740*
H3	0.55930	0.11850	−0.06060	0.0850*
H4	0.56900	0.31030	−0.14380	0.0810*
H5	0.60550	0.55040	−0.10370	0.0720*
H7	0.65760	0.65480	0.15950	0.0660*
H8A	0.62500	0.25360	0.18900	0.0740*
H8B	0.57670	0.38860	0.22320	0.0740*
H9A	0.70880	0.49390	0.27070	0.1100*
H9B	0.70910	0.32680	0.29720	0.1100*
H11	0.85550	0.54710	0.27720	0.0970*
H12	0.99720	0.51450	0.23580	0.1230*
H13	1.01510	0.31750	0.15710	0.1240*
H14	0.90240	0.15150	0.12280	0.1260*
H15	0.76900	0.18660	0.16250	0.0970*
H16A	0.63720	0.85100	0.05320	0.0720*
H16B	0.62690	0.78870	−0.02900	0.0720*
H17A	0.81720	0.89180	0.13870	0.1320*
H17B	0.90100	0.81790	0.11010	0.1320*
H17C	0.82610	0.71650	0.13690	0.1320*
H18A	0.77150	1.06730	−0.00340	0.1350*
H18B	0.75710	0.98570	−0.08120	0.1350*
H18C	0.85310	1.00490	−0.04030	0.1350*
H20	0.76290	0.71120	−0.14130	0.0870*
H21	0.80020	0.50590	−0.20790	0.1050*
H22	0.87920	0.31120	−0.14890	0.1110*
H23	0.92380	0.32550	−0.02280	0.1230*
H24	0.88370	0.52800	0.04640	0.1030*
HW1	0.589 (5)	0.705 (8)	0.294 (3)	0.1450*
HW2	0.542 (4)	0.598 (8)	0.325 (4)	0.1450*

	U11	U22	U33	U12	U13	U23
Si1	0.0692 (9)	0.0560 (7)	0.0610 (9)	−0.0105 (7)	0.0047 (7)	0.0011 (6)
N1	0.052 (2)	0.0482 (18)	0.049 (2)	0.0002 (17)	0.0098 (16)	−0.0020 (17)
N2	0.051 (2)	0.0471 (18)	0.054 (2)	0.0046 (16)	0.0102 (18)	0.0005 (17)
C1	0.038 (2)	0.055 (2)	0.053 (3)	0.0007 (18)	0.007 (2)	−0.005 (2)
C2	0.058 (3)	0.053 (3)	0.074 (4)	−0.003 (2)	0.010 (3)	−0.004 (2)
C3	0.074 (4)	0.064 (3)	0.074 (4)	−0.009 (3)	0.004 (3)	−0.021 (3)
C4	0.067 (3)	0.082 (4)	0.054 (3)	−0.003 (3)	0.007 (3)	−0.015 (3)
C5	0.056 (3)	0.069 (3)	0.055 (3)	0.002 (2)	0.009 (2)	0.004 (2)
C6	0.037 (2)	0.055 (2)	0.052 (3)	0.0032 (19)	0.0064 (19)	−0.003 (2)
C7	0.059 (3)	0.048 (3)	0.059 (3)	0.001 (2)	0.011 (2)	−0.007 (2)
C8	0.064 (3)	0.067 (3)	0.054 (3)	−0.010 (2)	0.014 (2)	0.001 (2)
C9	0.100 (5)	0.103 (5)	0.073 (4)	0.004 (4)	0.014 (4)	0.014 (3)
C10	0.088 (3)	0.081 (2)	0.070 (2)	−0.0050 (18)	−0.0026 (19)	0.0080 (16)
C11	0.088 (3)	0.081 (2)	0.070 (2)	−0.0050 (18)	−0.0026 (19)	0.0080 (16)
C12	0.074 (5)	0.111 (6)	0.122 (6)	−0.013 (4)	0.005 (4)	0.024 (5)
C13	0.070 (4)	0.119 (6)	0.120 (6)	−0.014 (4)	0.003 (4)	0.017 (5)
C14	0.095 (5)	0.107 (5)	0.116 (6)	−0.003 (4)	0.020 (4)	0.015 (4)
C15	0.088 (3)	0.081 (2)	0.070 (2)	−0.0050 (18)	−0.0026 (19)	0.0080 (16)
C16	0.074 (3)	0.046 (2)	0.061 (3)	0.004 (2)	0.012 (3)	0.002 (2)
C17	0.098 (5)	0.087 (4)	0.076 (4)	−0.004 (3)	−0.010 (3)	−0.011 (3)
C18	0.112 (5)	0.068 (3)	0.092 (5)	−0.018 (3)	0.019 (4)	0.015 (3)
C19	0.054 (3)	0.069 (3)	0.065 (3)	−0.017 (2)	0.004 (2)	0.002 (3)
C20	0.062 (4)	0.086 (4)	0.071 (4)	−0.004 (3)	0.012 (3)	0.000 (3)
C21	0.072 (4)	0.114 (5)	0.077 (4)	−0.008 (4)	0.012 (3)	−0.018 (4)
C22	0.081 (5)	0.093 (4)	0.105 (6)	−0.011 (4)	0.016 (4)	−0.031 (4)
C23	0.110 (6)	0.080 (4)	0.114 (6)	0.012 (4)	−0.001 (5)	−0.010 (4)
C24	0.101 (5)	0.076 (4)	0.075 (4)	0.004 (3)	−0.007 (3)	−0.005 (3)
Br1	0.0904 (4)	0.0581 (3)	0.0677 (4)	−0.0022 (3)	0.0101 (3)	−0.0092 (3)
OW1	0.100 (4)	0.092 (3)	0.092 (3)	−0.004 (2)	−0.008 (3)	0.005 (2)

Si1—C16	1.896 (5)	C22—C23	1.364 (11)
Si1—C17	1.853 (6)	C23—C24	1.391 (10)
Si1—C18	1.859 (4)	C2—H2	0.9300
Si1—C19	1.854 (4)	C3—H3	0.9300
OW1—HW1	0.83 (6)	C4—H4	0.9300
OW1—HW2	0.83 (6)	C5—H5	0.9300
N1—C8	1.467 (6)	C7—H7	0.9300
N1—C1	1.388 (6)	C8—H8B	0.9700
N1—C7	1.331 (6)	C8—H8A	0.9700
N2—C6	1.394 (6)	C9—H9B	0.9700
N2—C7	1.314 (6)	C9—H9A	0.9700
N2—C16	1.474 (6)	C11—H11	0.9300
C1—C2	1.393 (6)	C12—H12	0.9300
C1—C6	1.397 (7)	C13—H13	0.9300
C2—C3	1.371 (8)	C14—H14	0.9300
C3—C4	1.384 (8)	C15—H15	0.9300
C4—C5	1.368 (8)	C16—H16B	0.9700
C5—C6	1.376 (8)	C16—H16A	0.9700
C8—C9	1.523 (6)	C17—H17A	0.9600
C9—C10	1.488 (6)	C17—H17B	0.9600
C10—C11	1.391 (6)	C17—H17C	0.9600
C10—C15	1.347 (7)	C18—H18A	0.9600
C11—C12	1.419 (9)	C18—H18C	0.9600
C12—C13	1.351 (12)	C18—H18B	0.9600
C13—C14	1.378 (11)	C20—H20	0.9300
C14—C15	1.324 (11)	C21—H21	0.9300
C19—C24	1.392 (7)	C22—H22	0.9300
C19—C20	1.402 (5)	C23—H23	0.9300
C20—C21	1.374 (8)	C24—H24	0.9300
C21—C22	1.370 (10)
C16—Si1—C17	108.4 (3)	C6—C5—H5	121.00
C16—Si1—C18	106.39 (18)	N2—C7—H7	124.00
C16—Si1—C19	106.61 (19)	N1—C7—H7	124.00
C17—Si1—C18	111.8 (2)	N1—C8—H8A	109.00
C17—Si1—C19	111.2 (2)	C9—C8—H8A	109.00
C18—Si1—C19	112.12 (17)	C9—C8—H8B	109.00
HW1—OW1—HW2	109 (7)	H8A—C8—H8B	108.00
C1—N1—C8	125.4 (4)	N1—C8—H8B	109.00
C7—N1—C8	127.0 (4)	C8—C9—H9A	108.00
C1—N1—C7	107.7 (4)	C10—C9—H9A	108.00
C6—N2—C7	108.0 (4)	C10—C9—H9B	108.00
C6—N2—C16	127.0 (4)	C8—C9—H9B	108.00
C7—N2—C16	124.9 (4)	H9A—C9—H9B	107.00
N1—C1—C2	132.0 (5)	C12—C11—H11	120.00
N1—C1—C6	106.6 (4)	C10—C11—H11	120.00
C2—C1—C6	121.4 (5)	C11—C12—H12	122.00
C1—C2—C3	116.1 (5)	C13—C12—H12	122.00
C2—C3—C4	122.3 (5)	C12—C13—H13	119.00
C3—C4—C5	121.7 (5)	C14—C13—H13	119.00
C4—C5—C6	117.3 (5)	C15—C14—H14	120.00
N2—C6—C1	106.4 (4)	C13—C14—H14	120.00
N2—C6—C5	132.4 (4)	C14—C15—H15	119.00
C1—C6—C5	121.2 (4)	C10—C15—H15	119.00
N1—C7—N2	111.4 (4)	Si1—C16—H16A	109.00
N1—C8—C9	113.0 (4)	Si1—C16—H16B	109.00
C8—C9—C10	116.1 (3)	N2—C16—H16B	109.00
C9—C10—C11	117.5 (3)	H16A—C16—H16B	108.00
C11—C10—C15	118.4 (5)	N2—C16—H16A	109.00
C9—C10—C15	124.1 (5)	Si1—C17—H17B	109.00
C10—C11—C12	120.6 (5)	Si1—C17—H17C	109.00
C11—C12—C13	116.4 (7)	H17A—C17—H17B	109.00
C12—C13—C14	122.7 (7)	H17A—C17—H17C	110.00
C13—C14—C15	119.2 (7)	H17B—C17—H17C	110.00
C10—C15—C14	122.8 (7)	Si1—C17—H17A	109.00
Si1—C16—N2	112.3 (3)	Si1—C18—H18A	109.00
Si1—C19—C20	120.9 (3)	Si1—C18—H18C	110.00
Si1—C19—C24	122.4 (4)	H18A—C18—H18B	109.00
C20—C19—C24	116.5 (4)	H18A—C18—H18C	110.00
C19—C20—C21	121.6 (4)	H18B—C18—H18C	109.00
C20—C21—C22	120.6 (6)	Si1—C18—H18B	109.00
C21—C22—C23	119.5 (7)	C21—C20—H20	119.00
C22—C23—C24	120.5 (7)	C19—C20—H20	119.00
C19—C24—C23	121.3 (6)	C20—C21—H21	120.00
C1—C2—H2	122.00	C22—C21—H21	120.00
C3—C2—H2	122.00	C23—C22—H22	120.00
C2—C3—H3	119.00	C21—C22—H22	120.00
C4—C3—H3	119.00	C22—C23—H23	120.00
C5—C4—H4	119.00	C24—C23—H23	120.00
C3—C4—H4	119.00	C19—C24—H24	119.00
C4—C5—H5	121.00	C23—C24—H24	119.00
C18—Si1—C19—C24	140.9 (4)	C2—C1—C6—C5	−0.1 (7)
C17—Si1—C19—C20	−170.9 (3)	C2—C1—C6—N2	178.6 (4)
C17—Si1—C16—N2	−67.2 (4)	N1—C1—C6—C5	−178.2 (4)
C16—Si1—C19—C20	71.1 (3)	C1—C2—C3—C4	−0.7 (8)
C19—Si1—C16—N2	52.7 (4)	C2—C3—C4—C5	0.2 (9)
C17—Si1—C19—C24	15.0 (5)	C3—C4—C5—C6	0.3 (8)
C18—Si1—C16—N2	172.5 (3)	C4—C5—C6—N2	−178.7 (5)
C16—Si1—C19—C24	−103.0 (4)	C4—C5—C6—C1	−0.3 (7)
C18—Si1—C19—C20	−44.9 (3)	N1—C8—C9—C10	−53.3 (5)
C7—N1—C1—C6	−0.4 (5)	C8—C9—C10—C11	141.8 (4)
C8—N1—C1—C2	2.1 (7)	C8—C9—C10—C15	−39.3 (6)
C1—N1—C8—C9	130.7 (4)	C11—C10—C15—C14	0.8 (8)
C7—N1—C8—C9	−49.0 (6)	C9—C10—C11—C12	178.4 (5)
C8—N1—C1—C6	179.9 (4)	C15—C10—C11—C12	−0.6 (7)
C1—N1—C7—N2	0.0 (5)	C9—C10—C15—C14	−178.1 (6)
C7—N1—C1—C2	−178.2 (5)	C10—C11—C12—C13	0.7 (10)
C8—N1—C7—N2	179.8 (4)	C11—C12—C13—C14	−1.1 (12)
C16—N2—C6—C1	175.7 (4)	C12—C13—C14—C15	1.3 (13)
C16—N2—C6—C5	−5.8 (8)	C13—C14—C15—C10	−1.2 (11)
C16—N2—C7—N1	−176.0 (4)	Si1—C19—C20—C21	−175.0 (4)
C7—N2—C6—C5	178.0 (5)	C24—C19—C20—C21	−0.5 (6)
C6—N2—C7—N1	0.3 (5)	Si1—C19—C24—C23	175.9 (5)
C7—N2—C6—C1	−0.5 (5)	C20—C19—C24—C23	1.5 (8)
C6—N2—C16—Si1	−92.5 (5)	C19—C20—C21—C22	0.2 (8)
C7—N2—C16—Si1	83.1 (5)	C20—C21—C22—C23	−0.7 (10)
N1—C1—C2—C3	178.1 (5)	C21—C22—C23—C24	1.6 (11)
C6—C1—C2—C3	0.6 (7)	C22—C23—C24—C19	−2.0 (10)
N1—C1—C6—N2	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
OW1—HW1···Br1	0.83 (6)	2.57 (7)	3.365 (5)	160 (6)
OW1—HW2···Br1i	0.83 (6)	2.56 (7)	3.384 (5)	175 (6)
C7—H7···Br1	0.93	2.85	3.597 (5)	138
C8—H8A···Br1ii	0.97	2.89	3.822 (5)	160
C16—H16B···OW1iii	0.97	2.55	3.494 (7)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW1—HW1⋯Br1	0.83 (6)	2.57 (7)	3.365 (5)	160 (6)
OW1—HW2⋯Br1i	0.83 (6)	2.56 (7)	3.384 (5)	175 (6)
C7—H7⋯Br1	0.93	2.85	3.597 (5)	138
C8—H8A⋯Br1ii	0.97	2.89	3.822 (5)	160
C16—H16B⋯OW1iii	0.97	2.55	3.494 (7)	164

Symmetry codes: (i) ; (ii) ; (iii) .