2-[4-(Trifluoro­meth­oxy)phen­yl]-1H-benzimidazole

Nikhath Fathima; M S Krishnamurthy; Noor Shahina Begum

doi:10.1107/S1600536813001220

. 2013 Jan 19;69(Pt 2):o264. doi: 10.1107/S1600536813001220

2-[4-(Trifluoromethoxy)phenyl]-1H-benzimidazole

Nikhath Fathima ^a, M S Krishnamurthy ^a, Noor Shahina Begum ^a,^*

PMCID: PMC3569794 PMID: 23424540

Abstract

In the title compound, C₁₄H₉F₃N₂O, the best planes of the benzimidazole group and benzene ring form a dihedral angle of 26.68 (3)°. In the crystal, N—H⋯N hydrogen bonds link the molecules into infinite chains parallel to the c axis. Stacking interactions between the benzimidazole groups [centroid–centroid distance = 3.594 (5) Å] assemble the molecules into layers parallel to (100). The trifluoromethyl group is disordered over three sets of sites with site-occupancy factors of 0.787 (4), 0.107 (7) and 0.106 (7).

Related literature

For therapeutic and medicinal properties of benzimidazole derivatives, see: Chimirri et al. (1991 ▶); Benavides et al. (1995 ▶); Ishihara et al. (1994 ▶); Kubo et al. (1993 ▶). For related structures, see: Jian et al. (2006 ▶); Rashid, Tahir, Yusof et al. (2007 ▶); Rashid, Tahir, Kanwal et al. (2007 ▶). graphic file with name e-69-0o264-scheme1.jpg

Experimental

Crystal data

C₁₄H₉F₃N₂O
M _r = 278.23
Monoclinic,
a = 14.476 (6) Å
b = 9.312 (4) Å
c = 9.835 (4) Å
β = 108.192 (8)°
V = 1259.5 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 296 K
0.18 × 0.16 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.978, T _max = 0.980
6284 measured reflections
2209 independent reflections
1333 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.157
S = 1.00
2209 reflections
210 parameters
21 restraints
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and CAMERON (Watkin et al., 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Click here for additional data file.^{(16.2KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813001220/gk2550sup1.cif

e-69-0o264-sup1.cif^{(16.2KB, cif)}

Click here for additional data file.^{(106.4KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813001220/gk2550Isup2.hkl

e-69-0o264-Isup2.hkl^{(106.4KB, hkl)}

Click here for additional data file.^{(4.9KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813001220/gk2550Isup3.cml

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
N2—H21⋯N1ⁱ	0.86	2.07	2.864 (4)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance.

supplementary crystallographic information

Comment

Benzimidazole and its derivatives are known to exhibit a wide variety of pharmacological activities such as anti-HIV (Chimirri et al., 1991), antihistaminic (Benavides et al., 1995), antiulcer (Ishihara et al., 1994), antihypertensive (Kubo et al., 1993). The benzimidazole and phenyl groups form a dihedral angle of 26.68 (3)°. The bond lengths and angles of the benzimidazole moiety in the title compound are in good agreement with those observed in other benzimidazole derivatives (Jian et al., 2006; Rashid, Tahir, Yusof et al., 2007; Rashid, Tahir, Kanwal et al., 2007). The N1—C8 and N2—C8 distances were found to be 1.338 (5) Å and 1.356 (5) Å, respectively. The trifluoromethyl group is disordered over three sites with occupancy factors 0.787 (4), 0.107 (7) and 0.106 (7). The molecules are linked by intermolecular N—H···N hydrogen bonds to form infinite chains parallel to the c axis. Additionally, the crystal packing is further stabilized by π -π stacking interactions between the benzimidazole groups [interplanar distance 3.594 (5) Å].

Experimental

A mixture of 4-(trifluoromethoxy)benzaldehyde (10 mmol, 0.19 g) and o-phenyldiamine (10 mmol, 0.19 g) in benzene (2 ml) was refluxed for 6 h on a water bath. The reaction mixture was cooled. The solid separated, was filtered and dried (yield: 0.26 g, 75% and m.p. 503–508 K). Pale yellow crystals of the title compound were obtained by slow evaporation from a solution in ethyl acetate.