organic compounds
1-{[Dimethyl(phenyl)silyl]methyl}-3-(2-phenylethyl)-1H-benzimidazol-3-ium bromide monohydrate
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
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
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell 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
10.1107/S1600536812034915/nr2031sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812034915/nr2031Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812034915/nr2031Isup3.cml
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).
The water H atoms were located from a difference Fourier map and refined with distance restraints of O—H = 0.83 (2) Å and H···H = 1.35 (2) Å, and with Uiso(H) = 1.5 Ueq(O). The H atoms bonded to carbon atoms were positioned geometrically, with C—H = 0.93 Å (aromatic), 0.96 Å (methyl) and 0.97 Å (methylene) H atoms, respectively, and refined as riding with Uiso(H) = 1.5 Ueq(C) for the methyl groups and Uiso(H) = 1.2 Ueq(C) for others groups. Nine poorly fitted reflections (-2 0 2, -2 1 1, 7 2 0, 3 2 1, 0 1 6, 16 0 0, -4 0 2, -2 4 4, -2 1 7) were omitted from the refinement.
Data collection: X-AREA (Stoe & Cie, 2002); cell
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).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 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]. |
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 |
C24H27N2Si+·Br−·H2O | V = 2411.8 (3) Å3 |
Mr = 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)° |
Stoe IPDS 2 diffractometer | 5536 independent reflections |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | 3023 reflections with I > 2σ(I) |
Tmin = 0.656, Tmax = 0.803 | Rint = 0.074 |
19519 measured reflections |
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 | Δρmax = 0.82 e Å−3 |
5536 reflections | Δρmin = −0.53 e Å−3 |
244 parameters |
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 |
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 |
Mr | 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) |
Tmin, Tmax | 0.656, 0.803 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19519, 5536, 3023 |
Rint | 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 |
Δρmax, Δρmin (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).
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
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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.
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.