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

In the title compound, C(9)H(14)N(2)O(2), the imidazole ring and the acetate O-C=O plane make a dihedral angle of 80.54 (12)°. In the crystal, mol-ecules are connected via pairs of C-H⋯O hydrogen bonds, forming centrosymmetric dimers.

Related literature

For related structures, see: Pak et al. (2003 ▶); Wang et al. (2010 ▶).

Experimental

Crystal data

C9H14N2O2

M = 182.22

Monoclinic,

a = 10.558 (2) Å

b = 9.287 (2) Å

c = 11.047 (2) Å

β = 117.157 (4)°

V = 963.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.33 × 0.27 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.971, T max = 0.996

6535 measured reflections

2208 independent reflections

1688 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.097

S = 1.05

2208 reflections

121 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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/S1600536812001067/is5051sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812001067/is5051Isup2.hkl

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

C9H14N2O2	F(000) = 392
Mr = 182.22	Dx = 1.256 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 771 reflections
a = 10.558 (2) Å	θ = 3.0–29.0°
b = 9.287 (2) Å	µ = 0.09 mm−1
c = 11.047 (2) Å	T = 100 K
β = 117.157 (4)°	Plate, colorless
V = 963.9 (4) Å3	0.33 × 0.27 × 0.05 mm
Z = 4

Bruker APEXII CCD diffractometer	2208 independent reflections
Radiation source: fine-focus sealed tube	1688 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→13
Tmin = 0.971, Tmax = 0.996	k = −12→12
6535 measured reflections	l = −14→11

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0352P)2 + 0.2973P] where P = (Fo2 + 2Fc2)/3
2208 reflections	(Δ/σ)max < 0.001
121 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.27 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	0.58413 (11)	0.82030 (11)	0.21337 (11)	0.0244 (3)
O2	0.42983 (10)	0.63596 (10)	0.11631 (10)	0.0177 (2)
N1	1.01459 (13)	0.74927 (14)	0.30780 (13)	0.0250 (3)
N2	0.79333 (12)	0.67798 (12)	0.17766 (12)	0.0164 (3)
C1	0.91215 (15)	0.66189 (16)	0.29694 (15)	0.0210 (3)
H1	0.9207	0.5949	0.3653	0.025*
C2	0.95672 (16)	0.82623 (16)	0.18788 (16)	0.0231 (3)
H2	1.0055	0.8989	0.1650	0.028*
C3	0.82115 (15)	0.78441 (15)	0.10713 (15)	0.0197 (3)
H3	0.7584	0.8211	0.0198	0.024*
C4	0.65738 (15)	0.60761 (15)	0.13621 (15)	0.0188 (3)
H4A	0.6720	0.5166	0.1876	0.023*
H4B	0.6155	0.5835	0.0382	0.023*
C5	0.55466 (15)	0.70313 (15)	0.16122 (14)	0.0169 (3)
C6	0.30955 (14)	0.69930 (15)	0.13399 (14)	0.0178 (3)
C7	0.35240 (16)	0.71586 (17)	0.28396 (15)	0.0228 (3)
H7A	0.3916	0.6247	0.3308	0.034*
H7B	0.2688	0.7420	0.2957	0.034*
H7C	0.4245	0.7916	0.3225	0.034*
C8	0.26438 (16)	0.84140 (16)	0.05766 (16)	0.0230 (3)
H8A	0.3393	0.9133	0.1028	0.035*
H8B	0.1761	0.8747	0.0572	0.035*
H8C	0.2487	0.8278	−0.0362	0.035*
C9	0.19439 (15)	0.58562 (16)	0.06881 (15)	0.0230 (3)
H9A	0.1688	0.5775	−0.0281	0.034*
H9B	0.1102	0.6134	0.0790	0.034*
H9C	0.2299	0.4927	0.1135	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0231 (6)	0.0202 (5)	0.0320 (6)	−0.0045 (4)	0.0144 (5)	−0.0086 (4)
O2	0.0141 (5)	0.0182 (5)	0.0222 (5)	−0.0015 (4)	0.0096 (4)	−0.0035 (4)
N1	0.0185 (7)	0.0306 (7)	0.0238 (7)	−0.0012 (5)	0.0077 (6)	−0.0052 (6)
N2	0.0143 (6)	0.0174 (6)	0.0177 (6)	−0.0016 (5)	0.0075 (5)	−0.0027 (5)
C1	0.0195 (7)	0.0230 (7)	0.0192 (7)	0.0036 (6)	0.0076 (6)	0.0006 (6)
C2	0.0199 (7)	0.0233 (7)	0.0290 (8)	−0.0039 (6)	0.0138 (7)	−0.0026 (6)
C3	0.0213 (8)	0.0209 (7)	0.0191 (7)	0.0001 (6)	0.0111 (6)	0.0010 (6)
C4	0.0159 (7)	0.0177 (7)	0.0241 (8)	−0.0026 (5)	0.0102 (6)	−0.0037 (6)
C5	0.0163 (7)	0.0188 (7)	0.0148 (7)	−0.0015 (5)	0.0064 (6)	0.0003 (5)
C6	0.0147 (7)	0.0191 (7)	0.0210 (7)	0.0024 (5)	0.0094 (6)	−0.0002 (6)
C7	0.0218 (8)	0.0268 (8)	0.0216 (8)	0.0020 (6)	0.0116 (6)	−0.0015 (6)
C8	0.0216 (8)	0.0222 (7)	0.0259 (8)	0.0028 (6)	0.0114 (7)	0.0028 (6)
C9	0.0165 (8)	0.0241 (7)	0.0288 (8)	−0.0011 (6)	0.0107 (7)	−0.0011 (6)

O1—C5	1.2039 (17)	C4—H4B	0.9900
O2—C5	1.3325 (16)	C6—C7	1.513 (2)
O2—C6	1.4910 (16)	C6—C9	1.5207 (19)
N1—C1	1.3131 (19)	C6—C8	1.5209 (19)
N1—C2	1.379 (2)	C7—H7A	0.9800
N2—C1	1.3503 (18)	C7—H7B	0.9800
N2—C3	1.3709 (18)	C7—H7C	0.9800
N2—C4	1.4482 (17)	C8—H8A	0.9800
C1—H1	0.9500	C8—H8B	0.9800
C2—C3	1.353 (2)	C8—H8C	0.9800
C2—H2	0.9500	C9—H9A	0.9800
C3—H3	0.9500	C9—H9B	0.9800
C4—C5	1.5208 (19)	C9—H9C	0.9800
C4—H4A	0.9900
C5—O2—C6	121.56 (10)	O2—C6—C9	102.05 (11)
C1—N1—C2	104.32 (12)	C7—C6—C9	111.34 (12)
C1—N2—C3	106.85 (12)	O2—C6—C8	109.88 (11)
C1—N2—C4	127.15 (12)	C7—C6—C8	112.35 (12)
C3—N2—C4	125.75 (12)	C9—C6—C8	111.06 (12)
N1—C1—N2	112.36 (13)	C6—C7—H7A	109.5
N1—C1—H1	123.8	C6—C7—H7B	109.5
N2—C1—H1	123.8	H7A—C7—H7B	109.5
C3—C2—N1	110.88 (13)	C6—C7—H7C	109.5
C3—C2—H2	124.6	H7A—C7—H7C	109.5
N1—C2—H2	124.6	H7B—C7—H7C	109.5
C2—C3—N2	105.60 (13)	C6—C8—H8A	109.5
C2—C3—H3	127.2	C6—C8—H8B	109.5
N2—C3—H3	127.2	H8A—C8—H8B	109.5
N2—C4—C5	111.43 (11)	C6—C8—H8C	109.5
N2—C4—H4A	109.3	H8A—C8—H8C	109.5
C5—C4—H4A	109.3	H8B—C8—H8C	109.5
N2—C4—H4B	109.3	C6—C9—H9A	109.5
C5—C4—H4B	109.3	C6—C9—H9B	109.5
H4A—C4—H4B	108.0	H9A—C9—H9B	109.5
O1—C5—O2	126.65 (13)	C6—C9—H9C	109.5
O1—C5—C4	124.35 (13)	H9A—C9—H9C	109.5
O2—C5—C4	108.99 (11)	H9B—C9—H9C	109.5
O2—C6—C7	109.68 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4B···O2i	0.99	2.56	3.3768 (18)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4B⋯O2i	0.99	2.56	3.3768 (18)	140

Symmetry code: (i) .