Ethyl (E)-1-(2-styryl-1H-benzimidazol-1-yl)acetate.

In the title compound, C(19)H(18)NO(2), the dihedral angle between the benzimidazole and phenyl ring planes is 18.18 (17)°. The atoms of the ethyl side chain are disordered over two sets of sites in a 0.50:0.50 ratio. In the crystal, inter-molecular C-H⋯O hydrogen bonds and C-H⋯π contacts help to consolidate the packing.

Related literature

For further synthetic details, see: Hang & Ye (2008 ▶). For background on benzimidazoles, see: Göker et al. (1999 ▶); Özbey et al. (1998 ▶).

Experimental

Crystal data

C19H18N2O2

M = 307.36

Orthorhombic,

a = 12.021 (2) Å

b = 14.369 (3) Å

c = 9.7517 (18) Å

V = 1684.4 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 298 (2) K

0.25 × 0.25 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) T min = 0.884, T max = 0.984

16640 measured reflections

2046 independent reflections

1545 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.151

S = 1.07

2046 reflections

215 parameters

43 restraints

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809019825/hb2982sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019825/hb2982Isup2.hkl

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

C19H18N2O2	F(000) = 652
Mr = 307.36	Dx = 1.212 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 3237 reflections
a = 12.021 (2) Å	θ = 2.5–27.5°
b = 14.369 (3) Å	µ = 0.08 mm−1
c = 9.7517 (18) Å	T = 298 K
V = 1684.4 (5) Å3	Prism, colourless
Z = 4	0.25 × 0.25 × 0.20 mm

Rigaku SCXmini diffractometer	2046 independent reflections
Radiation source: fine-focus sealed tube	1545 reflections with I > 2σ(I)
graphite	Rint = 0.056
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 2.8°
CCD_Profile_fitting scans	h = −15→15
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −18→18
Tmin = 0.884, Tmax = 0.984	l = −12→12
16640 measured reflections

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0802P)2 + 0.1398P] where P = (Fo2 + 2Fc2)/3
2046 reflections
215 parameters	Δρmax = 0.16 e Å−3
43 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
N1	0.1633 (2)	0.13879 (18)	0.1323 (3)	0.0509 (6)
N2	0.0004 (2)	0.14329 (18)	0.0204 (3)	0.0558 (7)
C5	0.1630 (2)	0.0626 (2)	0.0454 (3)	0.0500 (7)
O1	0.3290 (2)	0.2529 (2)	0.0215 (3)	0.0743 (7)
O2	0.4352 (2)	0.2271 (2)	0.2042 (3)	0.0925 (10)
C3	0.3424 (3)	0.2197 (2)	0.1332 (4)	0.0570 (8)
C6	0.0611 (3)	0.0668 (2)	−0.0229 (4)	0.0543 (8)
C11	0.0644 (2)	0.1847 (2)	0.1111 (3)	0.0493 (7)
C12	0.0354 (3)	0.2693 (2)	0.1853 (4)	0.0559 (8)
H12A	0.0799	0.2873	0.2586	0.067*
C13	−0.0510 (3)	0.3216 (2)	0.1534 (4)	0.0587 (8)
H13A	−0.0924	0.3024	0.0780	0.070*
C14	−0.0894 (3)	0.4059 (2)	0.2221 (4)	0.0586 (8)
C4	0.2583 (3)	0.1664 (2)	0.2144 (3)	0.0539 (7)
H4A	0.2932	0.1113	0.2524	0.065*
H4B	0.2329	0.2046	0.2903	0.065*
C7	0.0364 (3)	−0.0019 (3)	−0.1204 (4)	0.0675 (10)
H7A	−0.0309	−0.0015	−0.1675	0.081*
C15	−0.1778 (4)	0.4562 (3)	0.1668 (5)	0.0794 (12)
H15A	−0.2105	0.4360	0.0856	0.095*
C19	−0.0430 (3)	0.4385 (3)	0.3420 (4)	0.0715 (10)
H19A	0.0171	0.4072	0.3806	0.086*
C9	0.2151 (4)	−0.0720 (3)	−0.0755 (4)	0.0763 (11)
H9A	0.2658	−0.1190	−0.0953	0.092*
C18	−0.0843 (4)	0.5169 (3)	0.4058 (5)	0.0863 (13)
H18A	−0.0519	0.5378	0.4867	0.104*
C8	0.1142 (4)	−0.0697 (3)	−0.1441 (5)	0.0804 (12)
H8A	0.0987	−0.1157	−0.2085	0.096*
C10	0.2420 (3)	−0.0058 (2)	0.0215 (4)	0.0652 (9)
H10A	0.3094	−0.0070	0.0684	0.078*
C16	−0.2178 (4)	0.5352 (3)	0.2300 (6)	0.0944 (14)
H16A	−0.2757	0.5686	0.1902	0.113*
C17	−0.1726 (5)	0.5644 (3)	0.3512 (6)	0.0941 (15)
H17A	−0.2015	0.6161	0.3962	0.113*
C1	0.5262 (14)	0.283 (2)	0.143 (3)	0.128 (3)	0.50
H1A	0.5213	0.2820	0.0437	0.153*	0.50
H1B	0.5218	0.3470	0.1738	0.153*	0.50
C2	0.628 (3)	0.241 (2)	0.188 (3)	0.137 (8)	0.50
H2B	0.6899	0.2732	0.1468	0.206*	0.50
H2C	0.6296	0.1769	0.1606	0.206*	0.50
H2D	0.6336	0.2453	0.2858	0.206*	0.50
C1'	0.5333 (14)	0.271 (2)	0.137 (3)	0.128 (3)	0.50
H1'A	0.5564	0.2338	0.0590	0.153*	0.50
H1'B	0.5147	0.3327	0.1058	0.153*	0.50
C2'	0.621 (3)	0.275 (2)	0.237 (3)	0.137 (8)	0.50
H2'A	0.6839	0.3070	0.1982	0.206*	0.50
H2'B	0.6429	0.2130	0.2622	0.206*	0.50
H2'C	0.5958	0.3078	0.3167	0.206*	0.50

	U11	U22	U33	U12	U13	U23
N1	0.0473 (13)	0.0574 (15)	0.0480 (13)	−0.0008 (12)	−0.0054 (12)	−0.0040 (13)
N2	0.0486 (13)	0.0628 (16)	0.0560 (15)	−0.0030 (13)	−0.0017 (13)	−0.0031 (15)
C5	0.0513 (17)	0.0551 (17)	0.0434 (17)	−0.0044 (15)	0.0014 (14)	−0.0030 (14)
O1	0.0745 (16)	0.0925 (18)	0.0560 (14)	−0.0139 (14)	−0.0052 (14)	0.0121 (15)
O2	0.0618 (15)	0.125 (2)	0.090 (2)	−0.0270 (16)	−0.0254 (16)	0.043 (2)
C3	0.0547 (18)	0.0639 (19)	0.0525 (19)	−0.0027 (16)	−0.0054 (15)	−0.0003 (17)
C6	0.0513 (18)	0.0607 (18)	0.0510 (17)	−0.0093 (15)	0.0032 (14)	−0.0006 (16)
C11	0.0451 (16)	0.0533 (16)	0.0495 (17)	−0.0047 (14)	0.0063 (14)	0.0020 (15)
C12	0.0571 (19)	0.0557 (18)	0.0550 (19)	−0.0045 (16)	0.0044 (15)	0.0012 (16)
C13	0.0571 (19)	0.0631 (19)	0.0560 (19)	0.0008 (16)	−0.0026 (15)	−0.0011 (17)
C14	0.0614 (19)	0.0538 (17)	0.0604 (19)	0.0014 (16)	0.0056 (18)	0.0043 (17)
C4	0.0559 (18)	0.0615 (16)	0.0442 (15)	−0.0003 (17)	−0.0074 (15)	0.0007 (16)
C7	0.060 (2)	0.074 (2)	0.068 (2)	−0.0138 (19)	−0.0028 (18)	−0.015 (2)
C15	0.082 (3)	0.071 (2)	0.085 (3)	0.016 (2)	−0.010 (2)	−0.005 (2)
C19	0.075 (2)	0.073 (2)	0.067 (2)	0.0104 (19)	0.0006 (19)	−0.005 (2)
C9	0.082 (3)	0.068 (2)	0.079 (2)	0.010 (2)	0.002 (2)	−0.017 (2)
C18	0.105 (3)	0.080 (3)	0.074 (3)	0.006 (3)	−0.003 (3)	−0.016 (2)
C8	0.089 (3)	0.072 (2)	0.080 (3)	−0.010 (2)	0.000 (2)	−0.027 (2)
C10	0.0597 (18)	0.0716 (19)	0.064 (2)	0.0050 (18)	−0.0025 (18)	−0.0081 (19)
C16	0.100 (4)	0.082 (3)	0.101 (3)	0.034 (3)	−0.008 (3)	−0.003 (3)
C17	0.112 (4)	0.074 (3)	0.096 (3)	0.025 (3)	0.022 (3)	−0.004 (3)
C1	0.078 (3)	0.160 (7)	0.145 (6)	−0.048 (4)	−0.024 (4)	0.068 (6)
C2	0.086 (5)	0.18 (2)	0.151 (19)	−0.025 (9)	−0.005 (10)	0.031 (12)
C1'	0.078 (3)	0.160 (7)	0.145 (6)	−0.048 (4)	−0.024 (4)	0.068 (6)
C2'	0.086 (5)	0.18 (2)	0.151 (19)	−0.025 (9)	−0.005 (10)	0.031 (12)

N1—C11	1.376 (4)	C15—H15A	0.9300
N1—C5	1.384 (4)	C19—C18	1.380 (6)
N1—C4	1.450 (4)	C19—H19A	0.9300
N2—C11	1.314 (4)	C9—C10	1.380 (5)
N2—C6	1.385 (4)	C9—C8	1.387 (6)
C5—C10	1.387 (5)	C9—H9A	0.9300
C5—C6	1.395 (4)	C18—C17	1.369 (7)
O1—C3	1.200 (5)	C18—H18A	0.9300
O2—C3	1.318 (4)	C8—H8A	0.9300
O2—C1	1.482 (9)	C10—H10A	0.9300
O2—C1'	1.485 (9)	C16—C17	1.367 (8)
C3—C4	1.495 (5)	C16—H16A	0.9300
C6—C7	1.402 (5)	C17—H17A	0.9300
C11—C12	1.457 (5)	C1—C2	1.434 (10)
C12—C13	1.318 (5)	C1—H1A	0.9700
C12—H12A	0.9300	C1—H1B	0.9700
C13—C14	1.459 (5)	C2—H2B	0.9600
C13—H13A	0.9300	C2—H2C	0.9600
C14—C19	1.378 (5)	C2—H2D	0.9600
C14—C15	1.393 (5)	C1'—C2'	1.436 (10)
C4—H4A	0.9700	C1'—H1'A	0.9700
C4—H4B	0.9700	C1'—H1'B	0.9700
C7—C8	1.370 (6)	C2'—H2'A	0.9600
C7—H7A	0.9300	C2'—H2'B	0.9600
C15—C16	1.378 (6)	C2'—H2'C	0.9600
C11—N1—C5	106.6 (2)	C10—C9—C8	121.3 (4)
C11—N1—C4	129.2 (3)	C10—C9—H9A	119.3
C5—N1—C4	123.8 (3)	C8—C9—H9A	119.3
C11—N2—C6	104.9 (3)	C17—C18—C19	120.7 (5)
N1—C5—C10	131.4 (3)	C17—C18—H18A	119.6
N1—C5—C6	105.1 (3)	C19—C18—H18A	119.6
C10—C5—C6	123.5 (3)	C7—C8—C9	122.2 (4)
C3—O2—C1	117.2 (11)	C7—C8—H8A	118.9
C3—O2—C1'	118.4 (10)	C9—C8—H8A	118.9
C1—O2—C1'	8(3)	C9—C10—C5	116.3 (4)
O1—C3—O2	124.0 (3)	C9—C10—H10A	121.8
O1—C3—C4	126.4 (3)	C5—C10—H10A	121.8
O2—C3—C4	109.6 (3)	C17—C16—C15	120.0 (5)
N2—C6—C5	110.6 (3)	C17—C16—H16A	120.0
N2—C6—C7	130.8 (3)	C15—C16—H16A	120.0
C5—C6—C7	118.7 (3)	C16—C17—C18	119.4 (4)
N2—C11—N1	112.9 (3)	C16—C17—H17A	120.3
N2—C11—C12	124.9 (3)	C18—C17—H17A	120.3
N1—C11—C12	122.2 (3)	C2—C1—O2	106 (2)
C13—C12—C11	123.1 (3)	C2—C1—H1A	110.5
C13—C12—H12A	118.4	O2—C1—H1A	110.5
C11—C12—H12A	118.4	C2—C1—H1B	110.5
C12—C13—C14	127.9 (3)	O2—C1—H1B	110.5
C12—C13—H13A	116.1	H1A—C1—H1B	108.6
C14—C13—H13A	116.1	C1—C2—H2B	109.5
C19—C14—C15	117.4 (4)	C1—C2—H2C	109.5
C19—C14—C13	122.9 (3)	H2B—C2—H2C	109.5
C15—C14—C13	119.6 (3)	C1—C2—H2D	109.5
N1—C4—C3	112.3 (3)	H2B—C2—H2D	109.5
N1—C4—H4A	109.1	H2C—C2—H2D	109.5
C3—C4—H4A	109.1	C2'—C1'—O2	108 (2)
N1—C4—H4B	109.1	C2'—C1'—H1'A	110.1
C3—C4—H4B	109.1	O2—C1'—H1'A	110.1
H4A—C4—H4B	107.9	C2'—C1'—H1'B	110.1
C8—C7—C6	118.0 (4)	O2—C1'—H1'B	110.1
C8—C7—H7A	121.0	H1'A—C1'—H1'B	108.4
C6—C7—H7A	121.0	C1'—C2'—H2'A	109.5
C16—C15—C14	121.4 (5)	C1'—C2'—H2'B	109.5
C16—C15—H15A	119.3	H2'A—C2'—H2'B	109.5
C14—C15—H15A	119.3	C1'—C2'—H2'C	109.5
C14—C19—C18	121.0 (4)	H2'A—C2'—H2'C	109.5
C14—C19—H19A	119.5	H2'B—C2'—H2'C	109.5
C18—C19—H19A	119.5
C11—N1—C5—C10	178.2 (4)	C12—C13—C14—C15	174.9 (4)
C4—N1—C5—C10	4.8 (5)	C11—N1—C4—C3	−91.5 (4)
C11—N1—C5—C6	−0.8 (3)	C5—N1—C4—C3	80.3 (4)
C4—N1—C5—C6	−174.2 (3)	O1—C3—C4—N1	13.5 (5)
C1—O2—C3—O1	2.3 (17)	O2—C3—C4—N1	−167.8 (3)
C1'—O2—C3—O1	−6.5 (17)	N2—C6—C7—C8	178.9 (4)
C1—O2—C3—C4	−176.4 (16)	C5—C6—C7—C8	−0.3 (5)
C1'—O2—C3—C4	174.8 (16)	C19—C14—C15—C16	−0.4 (6)
C11—N2—C6—C5	0.7 (4)	C13—C14—C15—C16	178.8 (4)
C11—N2—C6—C7	−178.6 (4)	C15—C14—C19—C18	1.2 (6)
N1—C5—C6—N2	0.1 (3)	C13—C14—C19—C18	−177.9 (4)
C10—C5—C6—N2	−179.0 (3)	C14—C19—C18—C17	0.0 (7)
N1—C5—C6—C7	179.5 (3)	C6—C7—C8—C9	−0.1 (7)
C10—C5—C6—C7	0.4 (5)	C10—C9—C8—C7	0.4 (7)
C6—N2—C11—N1	−1.2 (4)	C8—C9—C10—C5	−0.3 (6)
C6—N2—C11—C12	180.0 (3)	N1—C5—C10—C9	−178.9 (3)
C5—N1—C11—N2	1.3 (4)	C6—C5—C10—C9	−0.1 (5)
C4—N1—C11—N2	174.2 (3)	C14—C15—C16—C17	−1.7 (8)
C5—N1—C11—C12	−179.8 (3)	C15—C16—C17—C18	2.9 (8)
C4—N1—C11—C12	−7.0 (5)	C19—C18—C17—C16	−2.0 (8)
N2—C11—C12—C13	−11.1 (5)	C3—O2—C1—C2	−147.8 (16)
N1—C11—C12—C13	170.2 (3)	C1'—O2—C1—C2	−47 (14)
C11—C12—C13—C14	178.3 (3)	C3—O2—C1'—C2'	177.1 (14)
C12—C13—C14—C19	−5.9 (6)	C1—O2—C1'—C2'	94 (16)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O1i	0.97	2.47	3.409 (4)	162
C4—H4A···Cg2ii	0.97	2.67	3.577 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O1i	0.97	2.47	3.409 (4)	162
C4—H4A⋯Cg2ii	0.97	2.67	3.577 (4)	156

Symmetry codes: (i) ; (ii) ; (iii) .