2-[(1H-Benzimidazol-2-yl)sulfan-yl]-1-phenyl-ethanone.

The title compound, C(15)H(12)N(2)OS, 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, mol-ecules are linked by N-H⋯N hydrogen bonds into an infinite chain along [001]. The crystal packing also features a C-H⋯π inter-action.

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 = 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

Δρmax = 0.51 e Å−3

Δρmin = −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 ▶).

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

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

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

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

C15H12N2OS	F(000) = 560
Mr = 268.33	Dx = 1.389 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5435 reflections
a = 14.7849 (13) Å	θ = 2.6–30.0°
b = 9.2643 (8) Å	µ = 0.24 mm−1
c = 9.7859 (8) Å	T = 100 K
β = 106.792 (1)°	Needle, colourless
V = 1283.24 (19) Å3	0.32 × 0.11 × 0.07 mm
Z = 4

Bruker APEX DUO CCD diffractometer	3722 independent reflections
Radiation source: fine-focus sealed tube	3094 reflections with I > 2σ(I)'
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 30.0°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −20→20
Tmin = 0.927, Tmax = 0.983	k = −10→13
13644 measured reflections	l = −13→13

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.7649P] where P = (Fo2 + 2Fc2)/3
3722 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.51 e Å−3
0 restraints	Δρmin = −0.41 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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
S1	0.27768 (2)	0.54949 (4)	0.10069 (4)	0.02057 (9)
O1	0.12453 (8)	0.75548 (13)	0.11153 (13)	0.0336 (3)
N1	0.33134 (8)	0.80747 (12)	0.01048 (12)	0.0170 (2)
N2	0.34377 (8)	0.79475 (12)	0.24453 (12)	0.0159 (2)
C1	0.36703 (9)	0.93757 (14)	0.07565 (14)	0.0155 (2)
C2	0.39488 (9)	1.06192 (15)	0.01768 (15)	0.0195 (3)
H2A	0.3892	1.0686	−0.0793	0.023*
C3	0.43124 (10)	1.17483 (15)	0.10989 (15)	0.0209 (3)
H3A	0.4504	1.2587	0.0739	0.025*
C4	0.43994 (9)	1.16595 (15)	0.25666 (15)	0.0198 (3)
H4A	0.4649	1.2439	0.3154	0.024*
C5	0.41217 (9)	1.04368 (14)	0.31575 (14)	0.0179 (3)
H5A	0.4175	1.0378	0.4126	0.021*
C6	0.37587 (8)	0.93011 (13)	0.22273 (14)	0.0149 (2)
C7	0.31869 (9)	0.72789 (14)	0.11564 (14)	0.0163 (2)
C8	0.16524 (10)	0.57212 (15)	−0.03317 (16)	0.0224 (3)
H8A	0.1767	0.6038	−0.1212	0.027*
H8B	0.1340	0.4790	−0.0513	0.027*
C9	0.09888 (10)	0.67930 (16)	0.00635 (16)	0.0229 (3)
C10	0.00060 (10)	0.69134 (16)	−0.09324 (16)	0.0224 (3)
C11	−0.05419 (11)	0.80839 (17)	−0.07551 (18)	0.0277 (3)
H11A	−0.0292	0.8754	−0.0038	0.033*
C12	−0.14568 (12)	0.82596 (19)	−0.1637 (2)	0.0335 (4)
H12A	−0.1814	0.9051	−0.1520	0.040*
C13	−0.18359 (11)	0.7248 (2)	−0.26939 (19)	0.0340 (4)
H13A	−0.2448	0.7364	−0.3290	0.041*
C14	−0.13037 (11)	0.6066 (2)	−0.28627 (18)	0.0327 (4)
H14A	−0.1565	0.5380	−0.3559	0.039*
C15	−0.03793 (11)	0.58989 (18)	−0.19947 (17)	0.0271 (3)
H15A	−0.0020	0.5114	−0.2123	0.033*
H1N2	0.3370 (13)	0.761 (2)	0.325 (2)	0.030 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.02627 (17)	0.01719 (15)	0.01866 (18)	−0.00276 (12)	0.00714 (13)	−0.00024 (13)
O1	0.0277 (5)	0.0396 (6)	0.0327 (7)	−0.0016 (5)	0.0075 (5)	−0.0181 (5)
N1	0.0216 (5)	0.0182 (5)	0.0112 (5)	−0.0013 (4)	0.0048 (4)	−0.0010 (4)
N2	0.0204 (5)	0.0178 (5)	0.0098 (5)	−0.0002 (4)	0.0050 (4)	0.0009 (4)
C1	0.0172 (5)	0.0176 (6)	0.0114 (6)	0.0005 (4)	0.0036 (4)	−0.0004 (5)
C2	0.0236 (6)	0.0214 (6)	0.0132 (6)	−0.0005 (5)	0.0048 (5)	0.0026 (5)
C3	0.0249 (6)	0.0177 (6)	0.0199 (7)	−0.0014 (5)	0.0062 (5)	0.0023 (5)
C4	0.0213 (6)	0.0187 (6)	0.0185 (7)	−0.0007 (5)	0.0044 (5)	−0.0042 (5)
C5	0.0205 (6)	0.0209 (6)	0.0116 (6)	0.0007 (5)	0.0037 (5)	−0.0018 (5)
C6	0.0154 (5)	0.0165 (5)	0.0126 (6)	0.0012 (4)	0.0038 (4)	0.0011 (5)
C7	0.0182 (6)	0.0180 (6)	0.0128 (6)	0.0003 (5)	0.0046 (5)	−0.0003 (5)
C8	0.0242 (6)	0.0234 (6)	0.0202 (7)	−0.0050 (5)	0.0072 (5)	−0.0067 (6)
C9	0.0242 (6)	0.0237 (6)	0.0222 (7)	−0.0046 (5)	0.0093 (6)	−0.0047 (6)
C10	0.0237 (6)	0.0253 (7)	0.0200 (7)	−0.0053 (5)	0.0091 (5)	0.0006 (6)
C11	0.0300 (7)	0.0249 (7)	0.0291 (8)	−0.0027 (6)	0.0101 (6)	0.0002 (6)
C12	0.0302 (8)	0.0341 (8)	0.0376 (10)	0.0035 (7)	0.0120 (7)	0.0092 (7)
C13	0.0247 (7)	0.0469 (10)	0.0290 (9)	−0.0046 (7)	0.0056 (6)	0.0120 (8)
C14	0.0301 (7)	0.0440 (9)	0.0229 (8)	−0.0120 (7)	0.0056 (6)	−0.0025 (7)
C15	0.0271 (7)	0.0316 (8)	0.0233 (8)	−0.0059 (6)	0.0084 (6)	−0.0044 (6)

S1—C7	1.7519 (13)	C5—H5A	0.9300
S1—C8	1.8070 (15)	C8—C9	1.5222 (19)
O1—C9	1.2148 (18)	C8—H8A	0.9700
N1—C7	1.3224 (17)	C8—H8B	0.9700
N1—C1	1.3941 (16)	C9—C10	1.502 (2)
N2—C7	1.3571 (17)	C10—C11	1.394 (2)
N2—C6	1.3790 (16)	C10—C15	1.395 (2)
N2—H1N2	0.880 (19)	C11—C12	1.388 (2)
C1—C2	1.3977 (18)	C11—H11A	0.9300
C1—C6	1.4088 (18)	C12—C13	1.388 (3)
C2—C3	1.3846 (19)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.386 (3)
C3—C4	1.407 (2)	C13—H13A	0.9300
C3—H3A	0.9300	C14—C15	1.394 (2)
C4—C5	1.3869 (19)	C14—H14A	0.9300
C4—H4A	0.9300	C15—H15A	0.9300
C5—C6	1.3934 (18)
C7—S1—C8	100.07 (6)	C9—C8—H8A	108.6
C7—N1—C1	104.24 (11)	S1—C8—H8A	108.6
C7—N2—C6	106.56 (11)	C9—C8—H8B	108.6
C7—N2—H1N2	126.9 (12)	S1—C8—H8B	108.6
C6—N2—H1N2	126.3 (12)	H8A—C8—H8B	107.6
N1—C1—C2	130.08 (12)	O1—C9—C10	120.88 (13)
N1—C1—C6	109.64 (11)	O1—C9—C8	121.87 (13)
C2—C1—C6	120.26 (12)	C10—C9—C8	117.22 (12)
C3—C2—C1	117.56 (12)	C11—C10—C15	119.34 (14)
C3—C2—H2A	121.2	C11—C10—C9	117.71 (13)
C1—C2—H2A	121.2	C15—C10—C9	122.94 (13)
C2—C3—C4	121.66 (12)	C12—C11—C10	120.72 (15)
C2—C3—H3A	119.2	C12—C11—H11A	119.6
C4—C3—H3A	119.2	C10—C11—H11A	119.6
C5—C4—C3	121.51 (13)	C11—C12—C13	119.69 (16)
C5—C4—H4A	119.2	C11—C12—H12A	120.2
C3—C4—H4A	119.2	C13—C12—H12A	120.2
C4—C5—C6	116.68 (12)	C14—C13—C12	120.09 (15)
C4—C5—H5A	121.7	C14—C13—H13A	120.0
C6—C5—H5A	121.7	C12—C13—H13A	120.0
N2—C6—C5	132.10 (12)	C13—C14—C15	120.36 (16)
N2—C6—C1	105.56 (11)	C13—C14—H14A	119.8
C5—C6—C1	122.34 (12)	C15—C14—H14A	119.8
N1—C7—N2	114.00 (12)	C14—C15—C10	119.79 (15)
N1—C7—S1	125.75 (10)	C14—C15—H15A	120.1
N2—C7—S1	120.22 (10)	C10—C15—H15A	120.1
C9—C8—S1	114.65 (10)
C7—N1—C1—C2	179.02 (13)	C6—N2—C7—S1	177.86 (9)
C7—N1—C1—C6	0.78 (14)	C8—S1—C7—N1	−57.99 (13)
N1—C1—C2—C3	−177.79 (13)	C8—S1—C7—N2	124.34 (11)
C6—C1—C2—C3	0.30 (19)	C7—S1—C8—C9	−57.82 (11)
C1—C2—C3—C4	−0.1 (2)	S1—C8—C9—O1	8.48 (19)
C2—C3—C4—C5	−0.2 (2)	S1—C8—C9—C10	−173.67 (10)
C3—C4—C5—C6	0.38 (19)	O1—C9—C10—C11	11.0 (2)
C7—N2—C6—C5	−178.49 (13)	C8—C9—C10—C11	−166.86 (13)
C7—N2—C6—C1	0.55 (13)	O1—C9—C10—C15	−167.78 (15)
C4—C5—C6—N2	178.68 (13)	C8—C9—C10—C15	14.4 (2)
C4—C5—C6—C1	−0.22 (19)	C15—C10—C11—C12	−1.0 (2)
N1—C1—C6—N2	−0.83 (14)	C9—C10—C11—C12	−179.88 (14)
C2—C1—C6—N2	−179.28 (11)	C10—C11—C12—C13	0.9 (2)
N1—C1—C6—C5	178.32 (11)	C11—C12—C13—C14	0.3 (2)
C2—C1—C6—C5	−0.12 (19)	C12—C13—C14—C15	−1.4 (2)
C1—N1—C7—N2	−0.44 (15)	C13—C14—C15—C10	1.2 (2)
C1—N1—C7—S1	−178.24 (10)	C11—C10—C15—C14	0.0 (2)
C6—N2—C7—N1	−0.07 (15)	C9—C10—C15—C14	178.74 (14)

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

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

Symmetry codes: (i) ; (ii) .