3-Allyl-1-(2-cyano­benz­yl)-2-methyl­benzimidazol-3-ium bromide

Xiong-Bin Xu; Qiong Ye

doi:10.1107/S1600536807060874

. 2007 Dec 6;64(Pt 1):o23. doi: 10.1107/S1600536807060874

3-Allyl-1-(2-cyanobenzyl)-2-methylbenzimidazol-3-ium bromide

Xiong-Bin Xu ^a, Qiong Ye ^a,^*

PMCID: PMC2914985 PMID: 21200797

Abstract

In the title compound, C₁₉H₁₈N₃ ⁺·Br⁻, both the allyl and cyanophenyl groups are approximately perpendicular to the central benzimidazole unit, making dihedral angles of 89.7 (2) and 85.09 (13)°, respectively. The crystal packing is dominated by C—H⋯Br interactions, with each anion interacting with five neighboring cations.

Related literature

For olefin–copper coordination compounds, see: Ye et al. (2005 ▶). For the synthesis, see: Aakeroy et al. (2005 ▶). For a similar structure, see: Herrmann et al. (1997 ▶).

Experimental

Crystal data

C₁₉H₁₈N₃ ⁺·Br⁻
M _r = 368.27
Triclinic,
a = 9.123 (5) Å
b = 10.100 (4) Å
c = 10.520 (4) Å
α = 98.924 (2)°
β = 108.490 (18)°
γ = 102.851 (11)°
V = 869.2 (7) Å³
Z = 2
Mo Kα radiation
μ = 2.37 mm⁻¹
T = 293 (2) K
0.15 × 0.10 × 0.07 mm

Data collection

Rigaku Mercury2 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.872, T _max = 1.000 (expected range = 0.739–0.847)
9212 measured reflections
4233 independent reflections
3434 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.143
S = 0.92
4233 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Sheldrick, 1999 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807060874/fl2171sup1.cif

e-64-00o23-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807060874/fl2171Isup2.hkl

e-64-00o23-Isup2.hkl^{(207.4KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯Br1	0.93	2.91	3.738 (4)	149
C14—H14A⋯Br1ⁱ	0.97	2.82	3.740 (3)	158
C20—H20A⋯Br1ⁱⁱ	0.93	2.91	3.787 (4)	158
C29—H29A⋯Br1ⁱⁱⁱ	0.97	2.90	3.798 (3)	155
C29—H29B⋯Br1ⁱⁱ	0.97	2.91	3.848 (3)	164

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

Acknowledgments

This work was supported by a Start-up Grant from SEU to YQ.

supplementary crystallographic information

Comment

It has been almost a century since the discovery of olefin- copper coordination compounds. We are interested in obtaining stable olefin- copper(I) coordination compounds under solvothermal conditions since these compounds display novel cluster structures and interesting physical properties such as fluorescence, SHG and ferroelectric(Ye et al. (2005)). The title compound (Fig 1) was synthesized as part of this project. No unexpected bond distances and angles were found in (I). Both the allyl and cyano-phenyl groups are approximately perpendicular to the central benzimidazole moiety with dihedral angles of 89.72 (23)° and 85.09 (13)° respectively such that the phenyl ring and the olefin moeity are almost parallel to one another in a conformation similar to that found by Herrmann et al. (1997). Thus, the molecule could adopt an end-to-head or parallel packing mode to form tight stacking. However, no π-π interactions are found. Crystal packing is dominated by C—H···Br interactions with each anion cation interacting with five neighboring cations.

Experimental

2-((2-methyl-1H-benzo[d]imidazol-1-yl)methyl) benzonitrile (2.48 g) synthesized according to the procedure reported by (Aakeroy, et al.(2005) was dissolved in THF (30 ml) and allyl bromide;3- bromopropene (3.7 g) was added.The solution was stirred at 50° C for two days. The resulting white solid resultant was filterered out and washed twice with acetone to get 1.94 g of (I), (yield 66.7%). Colorless crystals suitable for X-ray diffraction were obtained by evaporation from methanol/water.