tert-Butyl 2-(1H-benzimidazol-1-yl)acetate.

In the title compound, C(13)H(16)N(2)O(2), the planes of the benzimidazole ring system and the acetate O-C=O fragment make a dihedral angle of 84.5 (3)°. In the crystal, mol-ecules are connected through C-H⋯N hydrogen bonds to form infinite chains in the [-110] direction.

Related literature

For related structures, see: Al-Mohammed et al. (2012 ▶); Fu et al. (2009 ▶); Xu et al. (2008 ▶).

Experimental

Crystal data

C13H16N2O2

M = 232.28

Monoclinic,

a = 5.4204 (2) Å

b = 11.3319 (4) Å

c = 19.8771 (7) Å

β = 96.609 (3)°

V = 1212.81 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.19 × 0.13 × 0.04 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.984, T max = 0.997

3829 measured reflections

1244 independent reflections

1091 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.076

S = 1.04

1244 reflections

157 parameters

2 restraints

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002814/gk2453sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002814/gk2453Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002814/gk2453Isup3.cml

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

C13H16N2O2	F(000) = 496
Mr = 232.28	Dx = 1.272 Mg m−3
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1057 reflections
a = 5.4204 (2) Å	θ = 3.6–26.4°
b = 11.3319 (4) Å	µ = 0.09 mm−1
c = 19.8771 (7) Å	T = 100 K
β = 96.609 (3)°	Tablet, colourless
V = 1212.81 (8) Å3	0.19 × 0.13 × 0.04 mm
Z = 4

Bruker APEXII CCD diffractometer	1244 independent reflections
Radiation source: fine-focus sealed tube	1091 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
φ and ω scans	θmax = 26.5°, θmin = 3.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.984, Tmax = 0.997	k = −14→14
3829 measured reflections	l = −24→24

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0394P)2 + 0.180P] where P = (Fo2 + 2Fc2)/3
1244 reflections	(Δ/σ)max < 0.001
157 parameters	Δρmax = 0.17 e Å−3
2 restraints	Δρmin = −0.20 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
O1	0.0330 (4)	0.41863 (16)	0.04890 (10)	0.0302 (5)
O2	0.2082 (3)	0.59850 (13)	0.07085 (9)	0.0174 (4)
N1	0.3020 (3)	0.38525 (17)	−0.05825 (10)	0.0193 (5)
N2	0.3571 (4)	0.19170 (18)	−0.07541 (12)	0.0243 (5)
C1	0.4419 (5)	0.2870 (2)	−0.04255 (14)	0.0227 (6)
H1	0.5871	0.2872	−0.0108	0.027*
C2	0.1057 (4)	0.3507 (2)	−0.10483 (12)	0.0183 (5)
C3	−0.0961 (4)	0.4127 (2)	−0.13641 (13)	0.0222 (6)
H3	−0.1195	0.4943	−0.1282	0.027*
C4	−0.2609 (5)	0.3489 (2)	−0.18058 (14)	0.0250 (6)
H4	−0.4014	0.3879	−0.2035	0.030*
C5	−0.2268 (5)	0.2281 (2)	−0.19258 (13)	0.0228 (6)
H5	−0.3446	0.1872	−0.2232	0.027*
C6	−0.0250 (5)	0.1677 (2)	−0.16060 (14)	0.0225 (6)
H6	−0.0019	0.0862	−0.1690	0.027*
C7	0.1446 (4)	0.2301 (2)	−0.11554 (13)	0.0192 (5)
C8	0.3234 (4)	0.4973 (2)	−0.02268 (13)	0.0183 (5)
H8A	0.2671	0.5617	−0.0544	0.022*
H8B	0.4997	0.5119	−0.0056	0.022*
C9	0.1684 (4)	0.4977 (2)	0.03638 (13)	0.0187 (5)
C10	0.0928 (4)	0.6199 (2)	0.13424 (13)	0.0200 (5)
C11	0.1856 (5)	0.5282 (2)	0.18666 (14)	0.0264 (6)
H11A	0.1199	0.4505	0.1722	0.040*
H11B	0.1293	0.5487	0.2303	0.040*
H11C	0.3675	0.5260	0.1914	0.040*
C12	0.1849 (5)	0.7429 (2)	0.15475 (15)	0.0256 (6)
H12A	0.3668	0.7432	0.1612	0.038*
H12B	0.1214	0.7655	0.1971	0.038*
H12C	0.1257	0.7992	0.1191	0.038*
C13	−0.1878 (5)	0.6198 (2)	0.11925 (15)	0.0271 (6)
H13A	−0.2380	0.6743	0.0819	0.041*
H13B	−0.2616	0.6451	0.1596	0.041*
H13C	−0.2454	0.5400	0.1065	0.041*

	U11	U22	U33	U12	U13	U23
O1	0.0402 (11)	0.0241 (10)	0.0279 (11)	−0.0125 (8)	0.0109 (9)	−0.0047 (9)
O2	0.0196 (9)	0.0158 (8)	0.0172 (9)	0.0005 (7)	0.0035 (7)	−0.0026 (7)
N1	0.0221 (11)	0.0165 (10)	0.0191 (12)	0.0029 (8)	0.0013 (9)	−0.0011 (9)
N2	0.0288 (12)	0.0191 (11)	0.0239 (12)	0.0041 (9)	−0.0013 (10)	−0.0012 (10)
C1	0.0253 (14)	0.0225 (13)	0.0196 (13)	0.0059 (11)	0.0001 (11)	−0.0002 (11)
C2	0.0214 (13)	0.0185 (12)	0.0153 (14)	0.0003 (10)	0.0037 (10)	−0.0018 (10)
C3	0.0249 (14)	0.0187 (12)	0.0224 (14)	0.0045 (10)	0.0001 (11)	−0.0023 (11)
C4	0.0273 (14)	0.0250 (14)	0.0221 (15)	0.0067 (11)	0.0008 (12)	−0.0008 (11)
C5	0.0266 (14)	0.0251 (14)	0.0163 (13)	0.0001 (11)	−0.0001 (11)	−0.0051 (11)
C6	0.0317 (15)	0.0164 (12)	0.0197 (14)	0.0010 (10)	0.0045 (11)	−0.0024 (10)
C7	0.0242 (14)	0.0186 (12)	0.0148 (13)	0.0031 (10)	0.0022 (10)	−0.0004 (10)
C8	0.0205 (12)	0.0176 (12)	0.0167 (13)	−0.0013 (10)	0.0019 (10)	−0.0030 (10)
C9	0.0210 (12)	0.0180 (12)	0.0163 (13)	0.0017 (10)	−0.0011 (10)	0.0007 (10)
C10	0.0188 (13)	0.0264 (13)	0.0152 (13)	−0.0015 (10)	0.0036 (10)	−0.0033 (11)
C11	0.0268 (14)	0.0341 (14)	0.0180 (13)	−0.0007 (12)	0.0016 (11)	0.0008 (12)
C12	0.0255 (13)	0.0250 (12)	0.0273 (15)	−0.0010 (11)	0.0071 (11)	−0.0092 (12)
C13	0.0167 (13)	0.0394 (15)	0.0255 (15)	−0.0004 (11)	0.0031 (11)	−0.0029 (13)

O1—C9	1.203 (3)	C6—C7	1.399 (4)
O2—C9	1.336 (3)	C6—H6	0.9500
O2—C10	1.490 (3)	C8—C9	1.520 (3)
N1—C1	1.363 (3)	C8—H8A	0.9900
N1—C2	1.384 (3)	C8—H8B	0.9900
N1—C8	1.451 (3)	C10—C11	1.516 (4)
N2—C1	1.317 (3)	C10—C13	1.516 (3)
N2—C7	1.394 (3)	C10—C12	1.520 (4)
C1—H1	0.9500	C11—H11A	0.9800
C2—C3	1.388 (3)	C11—H11B	0.9800
C2—C7	1.402 (3)	C11—H11C	0.9800
C3—C4	1.383 (4)	C12—H12A	0.9800
C3—H3	0.9500	C12—H12B	0.9800
C4—C5	1.406 (4)	C12—H12C	0.9800
C4—H4	0.9500	C13—H13A	0.9800
C5—C6	1.382 (4)	C13—H13B	0.9800
C5—H5	0.9500	C13—H13C	0.9800
C9—O2—C10	120.91 (18)	C9—C8—H8B	109.4
C1—N1—C2	106.6 (2)	H8A—C8—H8B	108.0
C1—N1—C8	126.3 (2)	O1—C9—O2	126.7 (2)
C2—N1—C8	125.84 (19)	O1—C9—C8	124.2 (2)
C1—N2—C7	104.24 (19)	O2—C9—C8	109.14 (18)
N2—C1—N1	113.8 (2)	O2—C10—C11	109.36 (19)
N2—C1—H1	123.1	O2—C10—C13	110.1 (2)
N1—C1—H1	123.1	C11—C10—C13	112.4 (2)
N1—C2—C3	131.6 (2)	O2—C10—C12	102.64 (19)
N1—C2—C7	105.1 (2)	C11—C10—C12	111.8 (2)
C3—C2—C7	123.3 (2)	C13—C10—C12	110.1 (2)
C4—C3—C2	116.1 (2)	C10—C11—H11A	109.5
C4—C3—H3	121.9	C10—C11—H11B	109.5
C2—C3—H3	121.9	H11A—C11—H11B	109.5
C3—C4—C5	122.0 (2)	C10—C11—H11C	109.5
C3—C4—H4	119.0	H11A—C11—H11C	109.5
C5—C4—H4	119.0	H11B—C11—H11C	109.5
C6—C5—C4	121.1 (2)	C10—C12—H12A	109.5
C6—C5—H5	119.5	C10—C12—H12B	109.5
C4—C5—H5	119.5	H12A—C12—H12B	109.5
C5—C6—C7	118.2 (2)	C10—C12—H12C	109.5
C5—C6—H6	120.9	H12A—C12—H12C	109.5
C7—C6—H6	120.9	H12B—C12—H12C	109.5
N2—C7—C6	130.4 (2)	C10—C13—H13A	109.5
N2—C7—C2	110.3 (2)	C10—C13—H13B	109.5
C6—C7—C2	119.4 (2)	H13A—C13—H13B	109.5
N1—C8—C9	111.03 (18)	C10—C13—H13C	109.5
N1—C8—H8A	109.4	H13A—C13—H13C	109.5
C9—C8—H8A	109.4	H13B—C13—H13C	109.5
N1—C8—H8B	109.4

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O1	0.98	2.47	3.033 (3)	116
C13—H13C···O1	0.98	2.42	2.995 (3)	117
C3—H3···N2i	0.95	2.48	3.406 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N2i	0.95	2.48	3.406 (3)	165

Symmetry code: (i) .