1,3-Bis(2-methyl-prop-2-eno-yl)-1H-benz-imidazol-2(3H)-one.

The mol-ecules of the title compound, C15H14N2O3, possesses crystallographically imposed twofold rotational symmetry, so the asymmetric unit contains one half-mol-ecule. The fused-ring system deviates significantly from planarity; the planes of the five- and six-membered rings are twisted with respect to each other by 3.0 (1)°. In the crystal, weak C-H⋯O hydrogen bonds link mol-ecules related by translation in [010] into chains.

Related literature

For applications of substituted benzimidazoles, see: Gravatt et al. (1994 ▶); Srikanth et al. (2011 ▶). For the crystal structures of related compounds, see: Ouzidan et al. (2011 ▶); Kandri Rodi et al. (2011 ▶).

Experimental

Crystal data

C15H14N2O3

M = 270.28

Monoclinic,

a = 16.6359 (9) Å

b = 8.8629 (5) Å

c = 9.6221 (4) Å

β = 102.775 (2)°

V = 1383.59 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.22 × 0.18 × 0.10 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.980, T max = 0.991

4086 measured reflections

1165 independent reflections

1042 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.208

S = 1.16

1165 reflections

93 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.36 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); 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 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011380/cv5390sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011380/cv5390Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011380/cv5390Isup3.cml

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

C15H14N2O3	F(000) = 568
Mr = 270.28	Dx = 1.298 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3023 reflections
a = 16.6359 (9) Å	θ = 2.6–28.4°
b = 8.8629 (5) Å	µ = 0.09 mm−1
c = 9.6221 (4) Å	T = 298 K
β = 102.775 (2)°	Prism, colourless
V = 1383.59 (12) Å3	0.22 × 0.18 × 0.10 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1165 independent reflections
Radiation source: fine-focus sealed tube	1042 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
phi and ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −16→19
Tmin = 0.980, Tmax = 0.991	k = −10→10
4086 measured reflections	l = −11→7

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.208	H-atom parameters constrained
S = 1.16	w = 1/[σ2(Fo2) + (0.1442P)2 + 0.5014P] where P = (Fo2 + 2Fc2)/3
1165 reflections	(Δ/σ)max < 0.001
93 parameters	Δρmax = 0.41 e Å−3
2 restraints	Δρmin = −0.36 e Å−3

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
C1	0.47013 (18)	0.8707 (3)	0.7898 (4)	0.0750 (10)
H1	0.4508	0.9622	0.8167	0.090*
C2	0.43851 (17)	0.7372 (3)	0.8301 (3)	0.0601 (8)
H2	0.3981	0.7370	0.8832	0.072*
C3	0.46936 (12)	0.6045 (2)	0.7882 (2)	0.0444 (6)
C4	0.5000	0.3574 (3)	0.7500	0.0437 (8)
C5	0.38571 (13)	0.4045 (2)	0.8743 (2)	0.0461 (7)
C6	0.34437 (13)	0.2572 (2)	0.8323 (2)	0.0529 (7)
N1	0.44820 (10)	0.45224 (19)	0.80638 (19)	0.0430 (6)
O1	0.5000	0.2222 (2)	0.7500	0.0654 (8)
O2	0.36526 (12)	0.4856 (2)	0.9606 (2)	0.0703 (7)
C7	0.31257 (19)	0.2319 (4)	0.6791 (2)	0.0781 (10)
H7A	0.3577	0.2117	0.6345	0.117*
H7B	0.2836	0.3201	0.6371	0.117*
H7C	0.2757	0.1472	0.6655	0.117*
C8	0.3311 (2)	0.1649 (4)	0.9330 (3)	0.0889 (11)
H8A	0.2999	0.0779	0.9084	0.107*
H8B	0.3529	0.1870	1.0284	0.107*

	U11	U22	U33	U12	U13	U23
C1	0.0787 (19)	0.0326 (12)	0.117 (3)	0.0049 (10)	0.0282 (17)	−0.0064 (13)
C2	0.0603 (15)	0.0416 (13)	0.0812 (19)	0.0069 (10)	0.0217 (14)	−0.0045 (11)
C3	0.0411 (11)	0.0326 (12)	0.0578 (14)	0.0014 (7)	0.0071 (10)	0.0007 (8)
C4	0.0413 (15)	0.0329 (14)	0.0592 (19)	0.000	0.0162 (13)	0.000
C5	0.0396 (11)	0.0463 (13)	0.0546 (14)	0.0070 (8)	0.0152 (10)	0.0035 (9)
C6	0.0398 (12)	0.0520 (13)	0.0710 (17)	−0.0020 (9)	0.0208 (11)	0.0046 (10)
N1	0.0389 (9)	0.0329 (10)	0.0599 (12)	0.0014 (6)	0.0166 (8)	0.0003 (7)
O1	0.0647 (16)	0.0316 (13)	0.111 (2)	0.000	0.0435 (15)	0.000
O2	0.0726 (13)	0.0674 (12)	0.0816 (14)	0.0023 (9)	0.0399 (11)	−0.0090 (9)
C7	0.0629 (17)	0.077 (2)	0.089 (2)	−0.0211 (13)	0.0050 (16)	0.0023 (15)
C8	0.100 (2)	0.081 (2)	0.095 (2)	−0.0197 (18)	0.0398 (19)	0.0097 (17)

C1—C1i	1.382 (6)	C5—O2	1.203 (3)
C1—C2	1.385 (4)	C5—N1	1.410 (3)
C1—H1	0.9300	C5—C6	1.489 (3)
C2—C3	1.378 (3)	C6—C8	1.3242 (19)
C2—H2	0.9300	C6—C7	1.4689 (19)
C3—C3i	1.383 (4)	C7—H7A	0.9600
C3—N1	1.415 (3)	C7—H7B	0.9600
C4—O1	1.198 (4)	C7—H7C	0.9600
C4—N1	1.397 (2)	C8—H8A	0.9300
C4—N1i	1.397 (2)	C8—H8B	0.9300
C1i—C1—C2	121.28 (17)	C8—C6—C7	124.0 (3)
C1i—C1—H1	119.4	C8—C6—C5	119.0 (2)
C2—C1—H1	119.4	C7—C6—C5	116.65 (19)
C3—C2—C1	117.3 (3)	C4—N1—C5	125.50 (19)
C3—C2—H2	121.4	C4—N1—C3	109.53 (17)
C1—C2—H2	121.4	C5—N1—C3	124.95 (17)
C2—C3—C3i	121.42 (15)	C6—C7—H7A	109.5
C2—C3—N1	131.2 (2)	C6—C7—H7B	109.5
C3i—C3—N1	107.37 (11)	H7A—C7—H7B	109.5
O1—C4—N1	127.01 (12)	C6—C7—H7C	109.5
O1—C4—N1i	127.01 (12)	H7A—C7—H7C	109.5
N1—C4—N1i	106.0 (2)	H7B—C7—H7C	109.5
O2—C5—N1	119.4 (2)	C6—C8—H8A	120.0
O2—C5—C6	121.8 (2)	C6—C8—H8B	120.0
N1—C5—C6	118.77 (18)	H8A—C8—H8B	120.0
C1i—C1—C2—C3	0.3 (6)	N1i—C4—N1—C3	−1.51 (11)
C1—C2—C3—C3i	1.4 (5)	O2—C5—N1—C4	153.7 (2)
C1—C2—C3—N1	−177.0 (2)	C6—C5—N1—C4	−28.9 (3)
O2—C5—C6—C8	−46.6 (4)	O2—C5—N1—C3	−24.6 (3)
N1—C5—C6—C8	136.0 (3)	C6—C5—N1—C3	152.8 (2)
O2—C5—C6—C7	126.7 (3)	C2—C3—N1—C4	−177.4 (2)
N1—C5—C6—C7	−50.7 (3)	C3i—C3—N1—C4	4.0 (3)
O1—C4—N1—C5	0.0 (2)	C2—C3—N1—C5	1.1 (4)
N1i—C4—N1—C5	180.0 (2)	C3i—C3—N1—C5	−177.4 (2)
O1—C4—N1—C3	178.48 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1ii	0.93	2.57	3.193 (3)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O1i	0.93	2.57	3.193 (3)	124

Symmetry code: (i) .