Ethyl 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetate.

In the title compound, C(8)H(11)N(3)O(4), the dihedral angle between the imidazole ring and the ethyl acetate plane is 103.1 (8)°. The crystal packing is stabilized by weak inter-molecular C-H⋯O and C-H⋯N hydrogen bonds.

Related literature

For the possible use of nitro­imidazole derivatives as radio sensitizers, to enhance the lethal effect of ionizing radiation on hypoxic tissues, see: Brown (1989 ▶); Chapman (1979 ▶); Chu et al. (2004 ▶).

Experimental

Crystal data

C8H11N3O4

M = 213.20

Orthorhombic,

a = 4.416 (3) Å

b = 10.290 (6) Å

c = 20.769 (12) Å

V = 943.7 (10) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 103 K

0.53 × 0.53 × 0.18 mm

Data collection

Rigaku SPIDER diffractometer

7883 measured reflections

1306 independent reflections

1161 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.082

S = 1.00

1306 reflections

138 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.20 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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/S1600536810037098/pv2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810037098/pv2327Isup2.hkl

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

C8H11N3O4	F(000) = 448
Mr = 213.20	Dx = 1.501 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2529 reflections
a = 4.416 (3) Å	θ = 3.6–27.6°
b = 10.290 (6) Å	µ = 0.12 mm−1
c = 20.769 (12) Å	T = 103 K
V = 943.7 (10) Å3	Chunk, colorless
Z = 4	0.53 × 0.53 × 0.18 mm

Rigaku SPIDER diffractometer	1161 reflections with I > 2σ(I)
Radiation source: Rotating Anode	Rint = 0.037
graphite	θmax = 27.6°, θmin = 3.6°
ω scans	h = −5→5
7883 measured reflections	k = −13→13
1306 independent reflections	l = −27→27

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.082	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0463P)2 + 0.16P] where P = (Fo2 + 2Fc2)/3
1306 reflections	(Δ/σ)max < 0.001
138 parameters	Δρmax = 0.24 e Å−3
0 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	0.3643 (3)	0.58804 (13)	0.42377 (6)	0.0166 (3)
O2	0.7058 (4)	0.74979 (13)	0.42394 (6)	0.0192 (3)
O3	1.0605 (4)	0.80751 (14)	0.14662 (6)	0.0249 (4)
O4	1.1820 (4)	1.00386 (14)	0.17463 (7)	0.0232 (4)
N1	0.5079 (4)	0.82884 (15)	0.30422 (7)	0.0138 (3)
N2	0.7748 (4)	1.00021 (15)	0.27284 (7)	0.0153 (4)
N3	1.0373 (4)	0.90341 (16)	0.18170 (7)	0.0177 (4)
C1	0.6719 (5)	0.78850 (18)	0.25230 (8)	0.0158 (4)
H1	0.6754	0.7046	0.2332	0.019*
C2	0.8285 (5)	0.89536 (18)	0.23422 (8)	0.0146 (4)
C3	0.5780 (5)	0.95693 (18)	0.31538 (9)	0.0154 (4)
C4	0.4430 (5)	1.03335 (19)	0.36860 (9)	0.0188 (4)
H4A	0.5425	1.1183	0.3711	0.023*
H4B	0.4712	0.9868	0.4093	0.023*
H4C	0.2262	1.0455	0.3606	0.023*
C5	0.3162 (5)	0.74537 (19)	0.34314 (8)	0.0163 (4)
H5A	0.2462	0.6708	0.3170	0.020*
H5B	0.1357	0.7945	0.3576	0.020*
C6	0.4893 (5)	0.69604 (18)	0.40139 (8)	0.0155 (4)
C7	0.5214 (5)	0.52893 (19)	0.47784 (9)	0.0200 (4)
H7A	0.4783	0.5775	0.5180	0.024*
H7B	0.7428	0.5295	0.4704	0.024*
C8	0.4071 (6)	0.39131 (19)	0.48318 (10)	0.0237 (5)
H8A	0.1868	0.3921	0.4889	0.028*
H8B	0.5021	0.3489	0.5203	0.028*
H8C	0.4582	0.3435	0.4438	0.028*

	U11	U22	U33	U12	U13	U23
O1	0.0165 (8)	0.0124 (6)	0.0210 (6)	−0.0005 (6)	0.0002 (6)	0.0040 (5)
O2	0.0182 (8)	0.0166 (7)	0.0228 (7)	−0.0028 (7)	−0.0031 (6)	−0.0004 (5)
O3	0.0315 (9)	0.0198 (7)	0.0233 (7)	0.0025 (8)	0.0062 (6)	−0.0028 (6)
O4	0.0218 (9)	0.0181 (7)	0.0298 (7)	−0.0029 (8)	0.0051 (6)	0.0062 (6)
N1	0.0141 (9)	0.0111 (7)	0.0161 (7)	−0.0023 (7)	−0.0004 (6)	0.0009 (6)
N2	0.0175 (9)	0.0113 (7)	0.0171 (7)	−0.0002 (7)	−0.0004 (6)	0.0006 (6)
N3	0.0188 (10)	0.0151 (8)	0.0191 (7)	0.0027 (8)	0.0007 (7)	0.0041 (6)
C1	0.0193 (11)	0.0118 (9)	0.0164 (8)	−0.0006 (9)	−0.0007 (8)	−0.0003 (7)
C2	0.0159 (10)	0.0128 (9)	0.0151 (8)	0.0010 (9)	−0.0004 (7)	0.0012 (7)
C3	0.0177 (11)	0.0093 (8)	0.0193 (8)	−0.0015 (8)	−0.0029 (8)	0.0004 (7)
C4	0.0225 (12)	0.0147 (9)	0.0193 (8)	0.0001 (9)	0.0018 (8)	−0.0004 (7)
C5	0.0144 (10)	0.0137 (9)	0.0207 (9)	−0.0033 (9)	0.0008 (7)	0.0029 (7)
C6	0.0163 (10)	0.0117 (8)	0.0184 (8)	0.0016 (9)	0.0042 (8)	−0.0009 (7)
C7	0.0219 (12)	0.0187 (10)	0.0193 (9)	0.0028 (9)	−0.0005 (8)	0.0058 (7)
C8	0.0308 (13)	0.0164 (10)	0.0239 (10)	0.0040 (10)	0.0011 (9)	0.0039 (8)

O1—C6	1.325 (2)	C3—C4	1.482 (3)
O1—C7	1.453 (2)	C4—H4A	0.9800
O2—C6	1.199 (2)	C4—H4B	0.9800
O3—N3	1.231 (2)	C4—H4C	0.9800
O4—N3	1.224 (2)	C5—C6	1.518 (3)
N1—C1	1.364 (2)	C5—H5A	0.9900
N1—C3	1.374 (2)	C5—H5B	0.9900
N1—C5	1.452 (2)	C7—C8	1.507 (3)
N2—C3	1.317 (3)	C7—H7A	0.9900
N2—C2	1.365 (2)	C7—H7B	0.9900
N3—C2	1.431 (2)	C8—H8A	0.9800
C1—C2	1.352 (3)	C8—H8B	0.9800
C1—H1	0.9500	C8—H8C	0.9800
C6—O1—C7	115.04 (16)	H4B—C4—H4C	109.5
C1—N1—C3	107.79 (17)	N1—C5—C6	110.35 (17)
C1—N1—C5	124.75 (16)	N1—C5—H5A	109.6
C3—N1—C5	127.24 (17)	C6—C5—H5A	109.6
C3—N2—C2	103.97 (16)	N1—C5—H5B	109.6
O4—N3—O3	124.24 (17)	C6—C5—H5B	109.6
O4—N3—C2	118.48 (16)	H5A—C5—H5B	108.1
O3—N3—C2	117.28 (17)	O2—C6—O1	125.57 (18)
C2—C1—N1	104.11 (16)	O2—C6—C5	123.93 (18)
C2—C1—H1	127.9	O1—C6—C5	110.49 (17)
N1—C1—H1	127.9	O1—C7—C8	106.88 (17)
C1—C2—N2	112.99 (17)	O1—C7—H7A	110.3
C1—C2—N3	126.05 (17)	C8—C7—H7A	110.3
N2—C2—N3	120.94 (17)	O1—C7—H7B	110.3
N2—C3—N1	111.11 (17)	C8—C7—H7B	110.3
N2—C3—C4	125.90 (17)	H7A—C7—H7B	108.6
N1—C3—C4	122.98 (18)	C7—C8—H8A	109.5
C3—C4—H4A	109.5	C7—C8—H8B	109.5
C3—C4—H4B	109.5	H8A—C8—H8B	109.5
H4A—C4—H4B	109.5	C7—C8—H8C	109.5
C3—C4—H4C	109.5	H8A—C8—H8C	109.5
H4A—C4—H4C	109.5	H8B—C8—H8C	109.5
C3—N1—C1—C2	−1.0 (2)	C1—N1—C3—N2	0.8 (2)
C5—N1—C1—C2	−176.05 (18)	C5—N1—C3—N2	175.61 (18)
N1—C1—C2—N2	1.0 (2)	C1—N1—C3—C4	−179.65 (18)
N1—C1—C2—N3	179.56 (18)	C5—N1—C3—C4	−4.8 (3)
C3—N2—C2—C1	−0.6 (2)	C1—N1—C5—C6	94.6 (2)
C3—N2—C2—N3	−179.20 (17)	C3—N1—C5—C6	−79.4 (2)
O4—N3—C2—C1	−173.7 (2)	C7—O1—C6—O2	−3.9 (3)
O3—N3—C2—C1	5.9 (3)	C7—O1—C6—C5	177.17 (16)
O4—N3—C2—N2	4.7 (3)	N1—C5—C6—O2	23.4 (3)
O3—N3—C2—N2	−175.69 (18)	N1—C5—C6—O1	−157.72 (16)
C2—N2—C3—N1	−0.1 (2)	C6—O1—C7—C8	−163.26 (16)
C2—N2—C3—C4	−179.70 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O4i	0.99	2.56	3.338 (3)	135
C5—H5A···N2i	0.99	2.56	3.509 (3)	160
C5—H5B···O2ii	0.99	2.39	3.175 (3)	136
C7—H7A···O2iii	0.99	2.46	3.362 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O4i	0.99	2.56	3.338 (3)	135
C5—H5A⋯N2i	0.99	2.56	3.509 (3)	160
C5—H5B⋯O2ii	0.99	2.39	3.175 (3)	136
C7—H7A⋯O2iii	0.99	2.46	3.362 (3)	151

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