Ethyl 2-(2-methyl-1H-benzimidazol-1-yl)acetate.

A new benzimidazole compound, C(12)H(14)N(2)O(2), has been synthesized by the reaction of 2-methyl-1H-benzimidazole and ethyl 2-bromo-acetate. In the crystal structure, weak inter-molecular C-H⋯N hydrogen bonds link the mol-ecules into chains. π⋯π Contacts (centroid⋯centroid distance = 3.713 Å) are observed. A C-H⋯π inter-action is also present. The N-C-C-O torsion angle is 178.4 (2)°.

Related literature

For related literature, see: Aaker et al. (2005 ▶).

Experimental

Crystal data

C12H14N2O2

M = 218.25

Monoclinic,

a = 10.854 (2) Å

b = 4.7959 (10) Å

c = 11.842 (2) Å

β = 111.42 (3)°

V = 573.9 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 295 (2) K

0.2 × 0.1 × 0.1 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.990, T max = 1.000 (expected range = 0.981–0.991)

5696 measured reflections

1323 independent reflections

1085 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.089

S = 1.12

1323 reflections

145 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.10 e Å−3

Δρmin = −0.15 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, New_Global_Publ_Block. DOI: 10.1107/S160053680802672X/wn2276sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802672X/wn2276Isup2.hkl

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

C12H14N2O2	F000 = 232
Mr = 218.25	Dx = 1.263 Mg m−3
Monoclinic, Pn	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P -2yac	Cell parameters from 6060 reflections
a = 10.854 (2) Å	θ = 6.4–55.1º
b = 4.7959 (10) Å	µ = 0.09 mm−1
c = 11.842 (2) Å	T = 295 (2) K
β = 111.42 (3)º	Prism, colorless
V = 573.9 (2) Å3	0.2 × 0.1 × 0.1 mm
Z = 2

Rigaku SCXmini diffractometer	1323 independent reflections
Radiation source: fine-focus sealed tube	1085 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.033
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 294(2) K	θmin = 3.2º
CCD_Profile_fitting scans	h = −14→14
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −6→6
Tmin = 0.990, Tmax = 1.000	l = −15→15
5696 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)] = 0.041	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0435P)2 + 0.018P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
1323 reflections	Δρmax = 0.10 e Å−3
145 parameters	Δρmin = −0.15 e Å−3
2 restraints	Extinction correction: none
Primary atom site location: structure-invariant direct methods

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 > 2σ(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
O2	0.14135 (17)	0.1457 (4)	0.20123 (14)	0.0515 (5)
C5	0.1006 (3)	−0.1654 (5)	−0.2701 (2)	0.0449 (6)
C1	0.3029 (2)	−0.2567 (6)	−0.0948 (2)	0.0471 (6)
H1A	0.3572	−0.2219	−0.0148	0.056*
N2	0.12080 (19)	0.0836 (4)	−0.10788 (17)	0.0412 (5)
C10	0.1019 (2)	0.0363 (5)	0.0906 (2)	0.0413 (5)
C9	0.1639 (2)	0.1907 (6)	0.0146 (2)	0.0425 (6)
H9A	0.1409	0.3867	0.0121	0.051*
H9B	0.2594	0.1753	0.0518	0.051*
N1	−0.0107 (2)	0.0004 (5)	−0.30007 (18)	0.0497 (6)
O1	0.0293 (2)	−0.1587 (4)	0.05777 (18)	0.0685 (6)
C4	0.1383 (3)	−0.3615 (6)	−0.3381 (2)	0.0576 (8)
H4A	0.0850	−0.3960	−0.4184	0.069*
C6	0.1845 (2)	−0.1163 (5)	−0.1499 (2)	0.0390 (6)
C7	0.0038 (2)	0.1447 (5)	−0.2017 (2)	0.0454 (6)
C2	0.3361 (3)	−0.4510 (7)	−0.1649 (2)	0.0540 (7)
H2A	0.4147	−0.5501	−0.1311	0.065*
C3	0.2550 (3)	−0.5027 (7)	−0.2850 (3)	0.0596 (7)
H3A	0.2805	−0.6350	−0.3296	0.072*
C12	0.1640 (3)	0.1400 (8)	0.4080 (3)	0.0737 (10)
H12A	0.1322	0.0602	0.4666	0.111*
H12B	0.1510	0.3383	0.4051	0.111*
H12C	0.2565	0.0999	0.4306	0.111*
C8	−0.0919 (3)	0.3503 (6)	−0.1883 (3)	0.0598 (8)
H8A	−0.1666	0.3635	−0.2632	0.090*
H8B	−0.0500	0.5293	−0.1683	0.090*
H8C	−0.1212	0.2914	−0.1248	0.090*
C11	0.0894 (3)	0.0179 (7)	0.2857 (3)	0.0617 (8)
H11A	0.1016	−0.1826	0.2873	0.074*
H11B	−0.0044	0.0568	0.2617	0.074*

	U11	U22	U33	U12	U13	U23
O2	0.0623 (12)	0.0550 (11)	0.0392 (10)	−0.0084 (9)	0.0209 (9)	−0.0061 (8)
C5	0.0512 (15)	0.0505 (15)	0.0271 (11)	−0.0146 (12)	0.0075 (11)	0.0011 (11)
C1	0.0448 (14)	0.0577 (16)	0.0327 (12)	−0.0087 (12)	0.0070 (10)	−0.0014 (12)
N2	0.0423 (11)	0.0447 (12)	0.0312 (10)	−0.0065 (9)	0.0069 (8)	−0.0003 (9)
C10	0.0419 (13)	0.0418 (13)	0.0383 (13)	0.0019 (11)	0.0126 (10)	−0.0012 (11)
C9	0.0452 (14)	0.0437 (15)	0.0345 (12)	−0.0095 (11)	0.0095 (10)	−0.0074 (10)
N1	0.0493 (12)	0.0502 (13)	0.0363 (12)	−0.0092 (11)	0.0000 (9)	0.0043 (10)
O1	0.0865 (15)	0.0659 (14)	0.0564 (12)	−0.0334 (12)	0.0301 (11)	−0.0148 (10)
C4	0.0744 (19)	0.0620 (18)	0.0291 (13)	−0.0186 (16)	0.0102 (13)	−0.0110 (13)
C6	0.0432 (13)	0.0434 (14)	0.0283 (12)	−0.0123 (11)	0.0104 (10)	0.0010 (10)
C7	0.0426 (14)	0.0450 (14)	0.0395 (14)	−0.0087 (12)	0.0041 (11)	0.0077 (11)
C2	0.0499 (15)	0.0627 (19)	0.0483 (17)	0.0003 (14)	0.0166 (13)	−0.0013 (14)
C3	0.0726 (19)	0.0613 (18)	0.0468 (17)	−0.0082 (15)	0.0242 (15)	−0.0129 (14)
C12	0.083 (2)	0.095 (3)	0.0472 (17)	0.0068 (19)	0.0283 (16)	0.0017 (17)
C8	0.0515 (16)	0.0546 (16)	0.0659 (19)	0.0001 (14)	0.0127 (14)	0.0089 (14)
C11	0.0716 (19)	0.073 (2)	0.0508 (18)	−0.0011 (16)	0.0346 (15)	−0.0009 (15)

O2—C10	1.329 (3)	C4—C3	1.370 (5)
O2—C11	1.451 (3)	C4—H4A	0.9300
C5—N1	1.380 (4)	C7—C8	1.482 (4)
C5—C4	1.393 (4)	C2—C3	1.395 (4)
C5—C6	1.401 (3)	C2—H2A	0.9300
C1—C2	1.380 (4)	C3—H3A	0.9300
C1—C6	1.385 (4)	C12—C11	1.497 (4)
C1—H1A	0.9300	C12—H12A	0.9600
N2—C6	1.376 (3)	C12—H12B	0.9600
N2—C7	1.379 (3)	C12—H12C	0.9600
N2—C9	1.446 (3)	C8—H8A	0.9600
C10—O1	1.193 (3)	C8—H8B	0.9600
C10—C9	1.502 (3)	C8—H8C	0.9600
C9—H9A	0.9700	C11—H11A	0.9700
C9—H9B	0.9700	C11—H11B	0.9700
N1—C7	1.315 (3)
C10—O2—C11	116.5 (2)	N1—C7—C8	125.7 (2)
N1—C5—C4	130.8 (2)	N2—C7—C8	122.1 (2)
N1—C5—C6	110.3 (2)	C1—C2—C3	121.8 (3)
C4—C5—C6	118.8 (3)	C1—C2—H2A	119.1
C2—C1—C6	116.5 (2)	C3—C2—H2A	119.1
C2—C1—H1A	121.7	C4—C3—C2	120.9 (3)
C6—C1—H1A	121.7	C4—C3—H3A	119.5
C6—N2—C7	107.06 (19)	C2—C3—H3A	119.5
C6—N2—C9	126.07 (19)	C11—C12—H12A	109.5
C7—N2—C9	126.7 (2)	C11—C12—H12B	109.5
O1—C10—O2	124.6 (2)	H12A—C12—H12B	109.5
O1—C10—C9	125.3 (2)	C11—C12—H12C	109.5
O2—C10—C9	110.04 (19)	H12A—C12—H12C	109.5
N2—C9—C10	112.00 (19)	H12B—C12—H12C	109.5
N2—C9—H9A	109.2	C7—C8—H8A	109.5
C10—C9—H9A	109.2	C7—C8—H8B	109.5
N2—C9—H9B	109.2	H8A—C8—H8B	109.5
C10—C9—H9B	109.2	C7—C8—H8C	109.5
H9A—C9—H9B	107.9	H8A—C8—H8C	109.5
C7—N1—C5	105.4 (2)	H8B—C8—H8C	109.5
C3—C4—C5	119.0 (3)	O2—C11—C12	107.0 (3)
C3—C4—H4A	120.5	O2—C11—H11A	110.3
C5—C4—H4A	120.5	C12—C11—H11A	110.3
N2—C6—C1	132.1 (2)	O2—C11—H11B	110.3
N2—C6—C5	105.0 (2)	C12—C11—H11B	110.3
C1—C6—C5	122.9 (2)	H11A—C11—H11B	108.6
N1—C7—N2	112.2 (2)
C11—O2—C10—O1	−1.1 (4)	C2—C1—C6—C5	0.2 (3)
C11—O2—C10—C9	180.0 (2)	N1—C5—C6—N2	0.1 (3)
C6—N2—C9—C10	−93.6 (3)	C4—C5—C6—N2	−179.8 (2)
C7—N2—C9—C10	80.8 (3)	N1—C5—C6—C1	179.1 (2)
O1—C10—C9—N2	2.6 (4)	C4—C5—C6—C1	−0.8 (4)
O2—C10—C9—N2	−178.4 (2)	C5—N1—C7—N2	0.6 (3)
C4—C5—N1—C7	179.5 (3)	C5—N1—C7—C8	−179.1 (2)
C6—C5—N1—C7	−0.4 (3)	C6—N2—C7—N1	−0.6 (3)
N1—C5—C4—C3	−179.0 (3)	C9—N2—C7—N1	−175.9 (2)
C6—C5—C4—C3	0.9 (4)	C6—N2—C7—C8	179.1 (2)
C7—N2—C6—C1	−178.6 (3)	C9—N2—C7—C8	3.9 (4)
C9—N2—C6—C1	−3.3 (4)	C6—C1—C2—C3	0.2 (4)
C7—N2—C6—C5	0.3 (2)	C5—C4—C3—C2	−0.5 (4)
C9—N2—C6—C5	175.6 (2)	C1—C2—C3—C4	−0.1 (4)
C2—C1—C6—N2	179.0 (3)	C10—O2—C11—C12	170.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···N1i	0.97	2.61	3.532 (3)	159
C8—H8C···Cg1ii	0.97	2.74	3.633 (5)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯N1i	0.97	2.61	3.532 (3)	159
C8—H8C⋯Cg1ii	0.97	2.74	3.633 (5)	155

Symmetry codes: (i) ; (ii) . Cg1 is the centroid of the imidazole ring.