2-(1H-Benzimidazol-1-yl)-1-phenyl-ethanone.

In the mol-ecule of the title compound, C(15)H(12)N(2)O, the planar benzimidazole system is oriented at a dihedral angle of 80.43 (5)° with respect to the phenyl ring. In the crystal structure, non-classical inter-molecular C-H⋯N and C-H⋯O hydrogen bonds link the mol-ecules into layers parallel to the ab plane.

Related literature

For general backgroud, see: Göker et al. (2002 ▶); Özden et al. (2004 ▶); Özel Güven et al. (2007a ▶,b ▶); Schar et al. (1976 ▶). For related literature, see: Peeters et al. (1997 ▶); Freer et al. (1986 ▶); Özel Güven et al. (2007 ▶).

Experimental

Crystal data

C15H12N2O

M = 236.27

Monoclinic,

a = 5.0475 (2) Å

b = 11.2319 (6) Å

c = 10.3517 (5) Å

β = 96.620 (3)°

V = 582.96 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 120 (2) K

0.45 × 0.22 × 0.03 mm

Data collection

Bruker–Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.962, T max = 0.997

6918 measured reflections

2639 independent reflections

2265 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.119

S = 1.06

2639 reflections

212 parameters

1 restraint

All H-atom parameters refined

Δρmax = 0.23 e Å−3

Δρmin = −0.22 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; 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, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808019107/si2097sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808019107/si2097Isup2.hkl

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

C15H12N2O	F000 = 248
Mr = 236.27	Dx = 1.346 Mg m−3
Monoclinic, P21	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1379 reflections
a = 5.0475 (2) Å	θ = 2.9–27.5º
b = 11.2319 (6) Å	µ = 0.09 mm−1
c = 10.3517 (5) Å	T = 120 (2) K
β = 96.620 (3)º	Plate, colorless
V = 582.96 (5) Å3	0.45 × 0.22 × 0.03 mm
Z = 2

Bruker–Nonius Roper CCD camera on κ-goniostat diffractometer	2639 independent reflections
Radiation source: fine-focus sealed tube	2265 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.057
Detector resolution: 9.091 pixels mm-1	θmax = 27.5º
T = 120(2) K	θmin = 3.6º
φ and ω scans	h = −6→6
Absorption correction: multi-scan(SADABS; Sheldrick, 2007)	k = −14→14
Tmin = 0.962, Tmax = 0.997	l = −13→13
6918 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	All H-atom parameters refined
wR(F2) = 0.119	w = 1/[σ2(Fo2) + (0.0651P)2 + 0.019P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
2639 reflections	Δρmax = 0.23 e Å−3
212 parameters	Δρmin = −0.22 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.091 (14)

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
O1	0.0968 (3)	0.55671 (14)	0.26162 (13)	0.0288 (4)
N1	0.3784 (3)	0.56655 (14)	0.05460 (15)	0.0236 (4)
N2	0.3592 (4)	0.41520 (16)	−0.08838 (17)	0.0301 (4)
C1	0.4848 (4)	0.46224 (19)	0.0180 (2)	0.0265 (4)
H1	0.651 (6)	0.432 (3)	0.074 (3)	0.048 (7)*
C2	0.1553 (4)	0.49603 (17)	−0.12561 (19)	0.0251 (4)
C3	−0.0424 (4)	0.49415 (19)	−0.2318 (2)	0.0288 (5)
H3	−0.051 (5)	0.422 (2)	−0.291 (2)	0.034 (6)*
C4	−0.2249 (4)	0.5857 (2)	−0.2443 (2)	0.0315 (5)
H4	−0.366 (5)	0.584 (3)	−0.317 (3)	0.045 (7)*
C5	−0.2133 (4)	0.67987 (19)	−0.1537 (2)	0.0293 (5)
H5	−0.340 (4)	0.742 (2)	−0.168 (2)	0.020 (5)*
C6	−0.0171 (4)	0.68387 (18)	−0.0477 (2)	0.0258 (4)
H6	−0.013 (5)	0.753 (3)	0.011 (3)	0.048 (7)*
C7	0.1634 (4)	0.59090 (17)	−0.03658 (18)	0.0237 (4)
C8	0.4659 (4)	0.63860 (18)	0.16674 (18)	0.0241 (4)
H81	0.481 (4)	0.720 (2)	0.143 (2)	0.025 (5)*
H82	0.642 (4)	0.609 (2)	0.203 (2)	0.025 (5)*
C9	0.2788 (4)	0.62815 (17)	0.27150 (18)	0.0222 (4)
C10	0.3283 (4)	0.70936 (18)	0.38542 (18)	0.0226 (4)
C11	0.5216 (4)	0.79730 (19)	0.39188 (18)	0.0273 (5)
H11	0.646 (4)	0.805 (2)	0.326 (2)	0.024 (5)*
C12	0.5582 (4)	0.8738 (2)	0.4985 (2)	0.0310 (5)
H12	0.695 (5)	0.934 (2)	0.503 (2)	0.031 (6)*
C13	0.3975 (4)	0.8617 (2)	0.5977 (2)	0.0351 (5)
H13	0.420 (5)	0.920 (3)	0.678 (3)	0.047 (7)*
C14	0.2068 (5)	0.7743 (2)	0.5926 (2)	0.0352 (5)
H14	0.089 (6)	0.761 (3)	0.658 (3)	0.061 (9)*
C15	0.1691 (4)	0.69726 (19)	0.4872 (2)	0.0284 (5)
H15	0.036 (4)	0.636 (2)	0.481 (2)	0.025 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0307 (7)	0.0341 (8)	0.0215 (7)	−0.0053 (6)	0.0026 (5)	0.0005 (6)
N1	0.0279 (8)	0.0236 (8)	0.0200 (8)	−0.0005 (7)	0.0049 (6)	−0.0003 (6)
N2	0.0377 (9)	0.0257 (8)	0.0282 (9)	−0.0016 (8)	0.0098 (7)	−0.0009 (7)
C1	0.0316 (10)	0.0239 (9)	0.0249 (10)	−0.0013 (8)	0.0071 (8)	0.0010 (8)
C2	0.0276 (9)	0.0245 (10)	0.0245 (10)	−0.0034 (8)	0.0085 (7)	−0.0015 (8)
C3	0.0341 (10)	0.0313 (11)	0.0219 (10)	−0.0098 (9)	0.0075 (8)	−0.0055 (8)
C4	0.0300 (11)	0.0417 (12)	0.0230 (10)	−0.0051 (9)	0.0034 (8)	0.0013 (8)
C5	0.0303 (10)	0.0336 (12)	0.0244 (10)	0.0019 (9)	0.0052 (8)	0.0009 (8)
C6	0.0297 (10)	0.0265 (10)	0.0222 (9)	0.0016 (8)	0.0072 (7)	−0.0015 (8)
C7	0.0271 (9)	0.0276 (10)	0.0170 (9)	−0.0050 (8)	0.0045 (7)	0.0006 (8)
C8	0.0269 (10)	0.0256 (11)	0.0200 (9)	−0.0007 (8)	0.0029 (8)	−0.0002 (8)
C9	0.0210 (9)	0.0241 (9)	0.0207 (9)	0.0012 (8)	−0.0003 (7)	0.0034 (7)
C10	0.0249 (9)	0.0246 (9)	0.0173 (9)	0.0043 (8)	−0.0022 (7)	0.0027 (7)
C11	0.0293 (10)	0.0311 (11)	0.0218 (10)	−0.0011 (9)	0.0041 (8)	0.0027 (8)
C12	0.0378 (11)	0.0294 (11)	0.0248 (10)	−0.0045 (10)	−0.0001 (9)	−0.0017 (8)
C13	0.0464 (13)	0.0341 (12)	0.0248 (11)	−0.0012 (10)	0.0043 (9)	−0.0040 (9)
C14	0.0414 (11)	0.0437 (13)	0.0222 (10)	−0.0004 (10)	0.0101 (9)	−0.0020 (9)
C15	0.0297 (10)	0.0311 (11)	0.0243 (10)	−0.0029 (9)	0.0032 (7)	0.0015 (8)

O1—C9	1.215 (2)	C7—C2	1.406 (3)
N1—C1	1.361 (3)	C8—H81	0.95 (3)
N1—C7	1.381 (2)	C8—H82	0.98 (2)
N1—C8	1.442 (3)	C9—C8	1.522 (3)
N2—C1	1.317 (3)	C10—C9	1.489 (3)
N2—C2	1.393 (3)	C10—C15	1.403 (3)
C1—H1	1.02 (3)	C11—C10	1.384 (3)
C3—C2	1.398 (3)	C11—C12	1.394 (3)
C3—C4	1.377 (3)	C11—H11	0.99 (2)
C3—H3	1.01 (3)	C12—H12	0.96 (3)
C4—H4	0.98 (3)	C13—C12	1.386 (3)
C5—C4	1.410 (3)	C13—C14	1.371 (3)
C5—H5	0.95 (2)	C13—H13	1.06 (3)
C6—C5	1.391 (3)	C14—C15	1.389 (3)
C6—C7	1.382 (3)	C14—H14	0.96 (3)
C6—H6	0.99 (3)	C15—H15	0.96 (2)
C1—N1—C7	106.55 (16)	N1—C8—H81	111.1 (13)
C1—N1—C8	127.82 (17)	N1—C8—H82	107.2 (13)
C7—N1—C8	125.63 (16)	C9—C8—H81	109.4 (13)
C1—N2—C2	103.83 (17)	C9—C8—H82	108.0 (13)
N1—C1—H1	116.9 (16)	H81—C8—H82	109.1 (19)
N2—C1—N1	114.25 (18)	O1—C9—C8	121.07 (16)
N2—C1—H1	128.8 (16)	O1—C9—C10	121.84 (17)
N2—C2—C3	130.22 (18)	C10—C9—C8	117.10 (15)
N2—C2—C7	110.35 (17)	C11—C10—C9	121.91 (17)
C3—C2—C7	119.43 (18)	C11—C10—C15	119.61 (18)
C2—C3—H3	117.7 (14)	C15—C10—C9	118.47 (18)
C4—C3—C2	118.14 (19)	C10—C11—C12	120.42 (18)
C4—C3—H3	124.0 (14)	C10—C11—H11	122.1 (13)
C3—C4—C5	121.5 (2)	C12—C11—H11	117.4 (13)
C3—C4—H4	118.4 (17)	C13—C12—C11	119.4 (2)
C5—C4—H4	120.1 (17)	C13—C12—H12	120.8 (15)
C6—C5—C4	121.3 (2)	C11—C12—H12	119.8 (15)
C6—C5—H5	120.4 (13)	C12—C13—H13	120.3 (15)
C4—C5—H5	118.3 (13)	C14—C13—C12	120.7 (2)
C5—C6—H6	118.1 (15)	C14—C13—H13	119.0 (15)
C7—C6—C5	116.34 (19)	C13—C14—C15	120.5 (2)
C7—C6—H6	125.5 (15)	C13—C14—H14	125 (2)
N1—C7—C2	105.01 (16)	C15—C14—H14	115 (2)
N1—C7—C6	131.69 (17)	C10—C15—H15	118.6 (13)
C6—C7—C2	123.30 (18)	C14—C15—C10	119.4 (2)
N1—C8—C9	111.88 (15)	C14—C15—H15	122.0 (13)
C7—N1—C1—N2	−0.3 (2)	N1—C7—C2—N2	0.66 (19)
C8—N1—C1—N2	178.87 (18)	N1—C7—C2—C3	−179.80 (17)
C1—N1—C7—C2	−0.21 (18)	C6—C7—C2—N2	−179.13 (17)
C1—N1—C7—C6	179.6 (2)	C6—C7—C2—C3	0.4 (3)
C8—N1—C7—C2	−179.44 (17)	O1—C9—C8—N1	7.0 (2)
C8—N1—C7—C6	0.3 (3)	C10—C9—C8—N1	−172.76 (16)
C1—N1—C8—C9	−105.9 (2)	C11—C10—C9—O1	−174.63 (18)
C7—N1—C8—C9	73.2 (2)	C11—C10—C9—C8	5.1 (3)
C2—N2—C1—N1	0.7 (2)	C15—C10—C9—O1	3.9 (3)
C1—N2—C2—C3	179.7 (2)	C15—C10—C9—C8	−176.38 (17)
C1—N2—C2—C7	−0.8 (2)	C9—C10—C15—C14	−178.14 (19)
C4—C3—C2—N2	178.8 (2)	C11—C10—C15—C14	0.4 (3)
C4—C3—C2—C7	−0.7 (3)	C10—C11—C12—C13	−0.6 (3)
C2—C3—C4—C5	0.6 (3)	C12—C11—C10—C9	178.37 (18)
C6—C5—C4—C3	−0.2 (3)	C12—C11—C10—C15	−0.1 (3)
C5—C6—C7—N1	−179.7 (2)	C14—C13—C12—C11	1.1 (3)
C5—C6—C7—C2	0.0 (3)	C12—C13—C14—C15	−0.8 (3)
C7—C6—C5—C4	−0.1 (3)	C13—C14—C15—C10	0.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H81···N2i	0.95 (2)	2.43 (2)	3.355 (3)	165.2 (17)
C8—H82···O1ii	0.98 (2)	2.38 (2)	3.351 (3)	170.1 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H81⋯N2i	0.95 (2)	2.43 (2)	3.355 (3)	165.2 (17)
C8—H82⋯O1ii	0.98 (2)	2.38 (2)	3.351 (3)	170.1 (17)

Symmetry codes: (i) ; (ii) .