1-{[Dimeth­yl(phen­yl)sil­yl]meth­yl}-3-(2-phenyl­eth­yl)-1H-benzimidazol-3-ium bromide monohydrate

Akkurt, M.; Küçükbay, H.; Şireci, N.; Büyükgüngör, O.

doi:10.1107/S1600536812034915

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages o2718-o2719

doi:10.1107/S1600536812034915

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1-{[Dimethyl(phenyl)silyl]methyl}-3-(2-phenylethyl)-1H-benzimidazol-3-ium bromide monohydrate

Mehmet Akkurt,^a ^* Hasan Küçükbay,^b Nihat Şireci ^c and Orhan Büyükgüngör ^d

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, Faculty of Arts and Sciences, Ínönü University, 44280 Malatya, Turkey, ^cDepartment of Chemistry, Faculty of Education, Adiyaman University, 02040 Adiyaman, Turkey, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 30 July 2012; accepted 7 August 2012; online 15 August 2012)

The title compound, C₂₄H₂₇N₂Si⁺·Br⁻·H₂O, was synthesized from 1-(dimethylphenylsilylmethyl)-1H-benzimidazole and (2-bromoethyl)benzene in dimethylformamide. 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, molecules are linked by O—H⋯Br, C—H⋯Br and C—H⋯O hydrogen bonds. In addition, the structure features π–π stacking interactions, 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_r = 469.48
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.069
wR(F²) = 0.173
S = 1.03
5536 reflections
244 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.82 e Å⁻³
Δρ_min = −0.53 e Å⁻³

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) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812034915/nr2031sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812034915/nr2031Isup3.cml

checkCIF report

Comment top

Heterocyclic compounds play an important role in biological systems and in many industrial fields. One of the these type heterocyclic compounds, benzimidazole is also an important pharmacophore in new drug designed and synthesized (Tavman et al., 2005; Küçükbay et al., 2004). Benzimidazol containing compounds o display a wide range of pharmacological activities, and are used for therapeutic purposes as anti-fungal, anti-bacterial, anti-helmintic, hypotensive, vasodilator, spasmolytic and anti-ulser activities. We also investigated their some anti-microbial activities (Küçükbay et al., 1995; Çetinkaya et al., 1996; Küçükbay et al., 2010; Küçükbay et al., 2011; Yılmaz et al., 2011). Alkylsilyl substituted benzimidazole derivatives exhibit important in vitro cytotoxic activity. For example, 1-(3-trimethylsilylpropyl)benzimidazole inhibits carcinoma S180 tumour growth in dose 1 mg.kg^-1 by 62% (on ICR mice) (Lukevics et al., 2001). The objective of this study is to synthesize and to elucidate the crystal structure of a new silyl benzimidazole compound.

In the title compound (I), (Fig. 1), the benzimidazole ring system (N1/N2/C1–C7) is nearly planar with a maximum deviation of 0.015 (5) Å for C6. The dihedral angle between the two terminal phenyl rings (C10–C15 and C19–C24) is 77.1 (3)°. The orientation of the two phenyl rings towards the benzimidazole-ring is remarkable [73.0 (3)° and 39.6 (2)°, respectively]. The values of the bond lengths and bond angles in (I) are in normal range, and they are in a good agreement with those found in similar compounds (Akkurt et al., 2010a,b; Baktır et al., 2010). The Si atom adopts distorted tetrahedral geometries in (I) and the angles around the Si atoms vary from 108.4 (3)° to 112.12 (17)°.

In the crystal, molecules are linked by O···H···Br, C—H···Br and C—H···O hydrogen bonds (Table 1 and Fig. 2). Furthermore, face-to-face π-π stacking interactions between parallel benzimidazole ring systems [Fig.3; Cg1···Cg2(1 - x, 1 - y, -z) = 3.644 (3) Å; where Cg1 and Cg2 are the centroids of the N1/N2/C1/C6/C7 and C1–C6 rings, respectively] help to the stabilization of the crystal structure.

Related literature top

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 top

A mixture of 1-(dimethylphenylsilylmethyl)benzimidazole (1.34 g, 5.0 mmol) and (2-bromoethyl)benzene (0.7 ml, 5.1 mmol) in dimethylformamide (5 ml) was refluxed for 3 h. The mixture was then cooled and the volatiles were removed under vacuum. The residue was crystallized from a dimethylformamide/ethanol (1:1). White crystals of the title compound (2.05 g, 87%) were obtained, mp 415–416 K: υ_(C=N) = 1557 cm^-1. Anal. found: C 61.12, H 6.21, N 5.56%. Calculated for C₂₄H₂₉BrN₂OSi: C 61.40, H 6.23, N 5.97%. ¹H NMR (δ, DMSO-d₆): 9.51 (s, 1H, NCHN), 8.02–7.99 (m, 2H, C₆H₄ ), 7.84–7.81 (m, 2H, C₆H₄ ), 7.62–7.19 (m, 10H, C₆H₅ phenethyl and 5H C₆H₅Si), 4.78 (t, 2H, CH₂ phenethyl, J= 7.2 Hz), 4.38 (s, 2H, CH₂Si), 3,20 (t, 2H, CH₂ phenethyl, J= 7.2 Hz) and 0.31 (s, 6H, Si(CH₃)₂). ¹³C NMR (δ, DMSO-d₆): 141.3 (NCHN), 137.3, 134.7, 134.3, 131.9, 131.1, 130.5, 129.2, 129.1, 128.5, 127.4, 126.9, 126.5, 114.3 and 114.0 (C₆H₄—ArH; C₆H₅– phenethyl and C₆H₅Si), 47.9 (CH₂ phenethyl), 37.9 (CH₂Si) 35.1 (CH₂ phenethyl), and -3.9 (Si(CH₃)₂).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); 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).

Figures top

The molecule of the title compound (I), showing the atom labelling scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.

View of the packing and hydrogen bonding interactions of (I) along the a axis in the unitcell. All hydrogen atoms not involved in hydrogen bonding, two phenyl rings and two ethyl groups have been omitted for clarity.

A view of the intermolecular face-to-face π–π stacking interactions between parallel benzimidazole ring systems, along the b axis in the crystal structure of (I). All hydrogen atoms, bromide ions and water molecules has been omitted for clarity. [Cg1 and Cg2 are the centroids of the N1/N2/C1/C6/C7 and C1–C6 rings, respectively. Symmetry code: (i) = 1 - x, 1 - y, -z].

1-{[Dimethyl(phenyl)silyl]methyl}-3-(2-phenylethyl)-1H-benzimidazol- 3-ium bromide monohydrate top

Crystal data top

C₂₄H₂₇N₂Si⁺·Br⁻·H₂O	F(000) = 976
M_r = 469.48	D_x = 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

Data collection top

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	R_int = 0.074
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.7°, θ_min = 2.3°
ω scans	h = −19→19
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→11
T_min = 0.656, T_max = 0.803	l = −23→22
19519 measured reflections

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)] = 0.069	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(F_o²) + (0.0795P)² + 0.0123P] where P = (F_o² + 2F_c²)/3
5536 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.82 e Å⁻³
3 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

C₂₄H₂₇N₂Si⁺·Br⁻·H₂O	V = 2411.8 (3) Å³
M_r = 469.48	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.1750 (11) Å	µ = 1.77 mm⁻¹
b = 8.9097 (6) Å	T = 296 K
c = 17.9440 (14) Å	0.26 × 0.20 × 0.13 mm
β = 96.235 (6)°

Data collection top

Stoe IPDS 2 diffractometer	5536 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3023 reflections with I > 2σ(I)
T_min = 0.656, T_max = 0.803	R_int = 0.074
19519 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	3 restraints
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.82 e Å⁻³
5536 reflections	Δρ_min = −0.53 e Å⁻³
244 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₇N₂Si⁺·Br⁻·H₂O
M_r	469.48
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	15.1750 (11), 8.9097 (6), 17.9440 (14)
β (°)	96.235 (6)
V (Å³)	2411.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.77
Crystal size (mm)	0.26 × 0.20 × 0.13

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.656, 0.803
No. of measured, independent and observed [I > 2σ(I)] reflections	19519, 5536, 3023
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.654

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.173, 1.03
No. of reflections	5536
No. of parameters	244
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.82, −0.53

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) −x+1, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x, −y+3/2, z−1/2.

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). HK and NŞ also thank the İnönü University Research Fund (project No. 2011/144) and the Adıyaman University Research Fund (ADYÜBAP-EFBAP2011–0008) for financial support of this study.

References

Akkurt, M., Çelik, Í., Küçükbay, H., Şireci, N. & Büyükgüngör, O. (2010a). Acta Cryst. E66, o1770–o1771. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Volume 68| Part 9| September 2012| Pages o2718-o2719

doi:10.1107/S1600536812034915

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

1-{[Dimeth­yl(phen­yl)sil­yl]meth­yl}-3-(2-phenyl­eth­yl)-1H-benzimidazol-3-ium bromide monohydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-{[Dimethyl(phenyl)silyl]methyl}-3-(2-phenylethyl)-1H-benzimidazol-3-ium bromide monohydrate