2-[(1H-Benzimidazol-2-yl)sulfan­yl]-1-phenyl­ethanone

Hatem A Abdel-Aziz; Tze Shyang Chia; Hoong-Kun Fun

doi:10.1107/S1600536812028747

. 2012 Jun 30;68(Pt 7):o2262. doi: 10.1107/S1600536812028747

2-[(1H-Benzimidazol-2-yl)sulfanyl]-1-phenylethanone

Hatem A Abdel-Aziz ^a, Tze Shyang Chia ^b, Hoong-Kun Fun ^b,^*,^‡

PMCID: PMC3394045 PMID: 22798910

Abstract

The title compound, C₁₅H₁₂N₂OS, adopts a twisted V-shape, with the S atom as the pivot. The benzimidazole ring system [maximum deviation = 0.015 (1) Å] makes a dihedral angle of 78.56 (7)° with the phenyl ring. The O atom of the ketone group is close to coplanar with its adjacent ring [O—C—C—C torsion angle = 11.0 (2)°]. In the crystal, molecules are linked by N—H⋯N hydrogen bonds into an infinite chain along [001]. The crystal packing also features a C—H⋯π interaction.

Related literature

For a related structure. see: Abdel-Aziz et al. (2011 ▶). For the synthesis, see: D’Amico et al. (1964 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond lengths, see: Allen et al. (1987) ▶.

Experimental

Crystal data

C₁₅H₁₂N₂OS
M _r = 268.33
Monoclinic,
a = 14.7849 (13) Å
b = 9.2643 (8) Å
c = 9.7859 (8) Å
β = 106.792 (1)°
V = 1283.24 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 K
0.32 × 0.11 × 0.07 mm

Data collection

Bruker APEX DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.927, T _max = 0.983
13644 measured reflections
3722 independent reflections
3094 reflections with I > 2σ(I)’
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.096
S = 1.05
3722 reflections
176 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812028747/hb6869sup1.cif

e-68-o2262-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812028747/hb6869Isup2.hkl

e-68-o2262-Isup2.hkl^{(182.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812028747/hb6869Isup3.cml

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

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

Cg1 is the centroid of the N1/N2/C1/C6/C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯N1ⁱ	0.880 (19)	1.95 (2)	2.8250 (16)	175.8 (18)
C4—H4A⋯Cg1ⁱⁱ	0.93	2.82	3.4175 (15)	123

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

Acknowledgments

HKF and TSC thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSC also thanks the Malaysian Government and USM for the award of a research fellowship. The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University.

supplementary crystallographic information

Comment

In continuation to our reports on the chemistry and the biological activity of benzimidazoles (Abdel-Aziz et al., 2011), we report herein the crystal structure of the title compound.

The asymmetric unit of the title compound is shown in Fig. 1. The molecule adopts a twisted V shape with S atom as the pivot, which is identical to a related structure (Abdel-Aziz et al., 2011). The benzimidazole ring system (N1/N2/C1–C7) is essentially planar [maximum deviation = 0.015 (1) Å at atom C1] and makes a dihedral angle of 78.56 (7)° with the terminal C10–C15 benzene ring. The ketone group (C9═O1) is almost coplanar with the C10–C15 benzene ring as indicated by the O1—C9—C10—C11 torsion angle of 11.0 (2)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal (Fig. 2), molecules are linked by N2—H1N2···N1 hydrogen bond into an infinite chain along the c-axis. The crystal packing is further stabilized by C—H···π interaction (Table 1), involving Cg1, which is the centroid of N1/N2/C1/C6/C7 ring.

Experimental

The title compound was prepared by the reaction of 1H-benzo[d]imidazole-2-thiol and 2-bromo-1-phenylethanone in ethanol in the presence of potassium hydroxide (D'Amico et al., 1964). Colourless needles were crystallised from ethanol solution.