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

In the crystal of the title compound, C7H9N3O4, mol-ecules are linked by weak C-H⋯O hydrogen bonds into chains along the a-axis direction. The dihedral angle between the ring and the nitro group is 3.03 (6), while that between the ring and the acetate group is 85.01 (3)°.

Related literature

For the synthesis of the title compound, see: Pavlik et al. (2011 ▶); Kasai et al. (2001 ▶). For the structural identification of nitro­imidazoles, see: Larina & Lopyrev (2009 ▶). For biological activities of this class of compounds, see: Gaonkar et al. (2009 ▶); Olender et al. (2009 ▶). For our previous work on imidazole derivatives, see: Chelghoum et al. (2011 ▶); Bahnous et al. (2012 ▶).

Experimental

Crystal data

C7H9N3O4

M = 199.17

Monoclinic,

a = 4.6619 (2) Å

b = 17.3256 (7) Å

c = 11.1490 (4) Å

β = 103.204 (2)°

V = 876.70 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 150 K

0.35 × 0.3 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.937, T max = 0.985

7665 measured reflections

1991 independent reflections

1753 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.088

S = 1.09

1991 reflections

129 parameters

H-atom parameters constrained

Δρmax = 0.26 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CRYSCAL (local program).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011914/yk2093sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011914/yk2093Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813011914/yk2093Isup3.cml

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

C7H9N3O4	F(000) = 416
Mr = 199.17	Dx = 1.509 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3719 reflections
a = 4.6619 (2) Å	θ = 3.8–27.5°
b = 17.3256 (7) Å	µ = 0.13 mm−1
c = 11.1490 (4) Å	T = 150 K
β = 103.204 (2)°	Prism, colourless
V = 876.70 (6) Å3	0.35 × 0.3 × 0.12 mm
Z = 4

Bruker APEXII CCD diffractometer	1753 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.8°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −6→5
Tmin = 0.937, Tmax = 0.985	k = −22→22
7665 measured reflections	l = −14→13
1991 independent 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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0409P)2 + 0.2051P] where P = (Fo2 + 2Fc2)/3
1991 reflections	(Δ/σ)max = 0.002
129 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.21 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
C1	0.6041 (3)	−0.02718 (8)	0.85178 (13)	0.0358 (3)
H1A	0.5668	−0.0689	0.7909	0.054*
H1B	0.5828	−0.0469	0.9317	0.054*
H1C	0.8046	−0.0075	0.8596	0.054*
O2	0.39315 (19)	0.03498 (5)	0.81191 (8)	0.0303 (2)
C3	0.4191 (2)	0.06977 (6)	0.70857 (10)	0.0215 (2)
O4	0.58536 (18)	0.05011 (5)	0.64611 (8)	0.0268 (2)
C5	0.2106 (3)	0.13799 (6)	0.67831 (10)	0.0227 (2)
H5A	0.0069	0.1194	0.6459	0.027*
H5B	0.2144	0.1684	0.7538	0.027*
N6	0.3015 (2)	0.18625 (5)	0.58664 (8)	0.0199 (2)
C7	0.2472 (2)	0.17282 (6)	0.46184 (10)	0.0201 (2)
N8	0.4024 (2)	0.21960 (5)	0.40814 (8)	0.0215 (2)
C9	0.5615 (2)	0.26266 (6)	0.50325 (10)	0.0199 (2)
C10	0.5056 (2)	0.24382 (6)	0.61419 (10)	0.0211 (2)
H10	0.5892	0.2657	0.6925	0.025*
C11	0.0408 (3)	0.11215 (7)	0.39924 (11)	0.0277 (3)
H11A	−0.0054	0.1211	0.3101	0.042*
H11B	−0.1411	0.1141	0.4292	0.042*
H11C	0.1327	0.0613	0.4172	0.042*
N12	0.7683 (2)	0.31975 (5)	0.48349 (9)	0.0228 (2)
O13	0.80836 (19)	0.32840 (5)	0.37915 (8)	0.0315 (2)
O14	0.8988 (2)	0.35710 (5)	0.57330 (8)	0.0361 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0406 (7)	0.0303 (7)	0.0373 (7)	0.0065 (6)	0.0110 (6)	0.0126 (6)
O2	0.0335 (5)	0.0293 (5)	0.0315 (5)	0.0039 (4)	0.0143 (4)	0.0106 (4)
C3	0.0218 (5)	0.0203 (5)	0.0228 (5)	−0.0043 (4)	0.0061 (4)	0.0001 (4)
O4	0.0290 (4)	0.0248 (4)	0.0293 (4)	0.0039 (3)	0.0124 (4)	0.0003 (3)
C5	0.0231 (6)	0.0243 (6)	0.0235 (6)	0.0000 (4)	0.0112 (4)	0.0016 (4)
N6	0.0223 (5)	0.0196 (4)	0.0191 (5)	0.0021 (4)	0.0075 (4)	−0.0002 (3)
C7	0.0198 (5)	0.0208 (5)	0.0197 (5)	0.0062 (4)	0.0045 (4)	−0.0001 (4)
N8	0.0232 (5)	0.0230 (5)	0.0185 (5)	0.0051 (4)	0.0054 (4)	0.0013 (4)
C9	0.0215 (5)	0.0177 (5)	0.0215 (5)	0.0037 (4)	0.0068 (4)	0.0014 (4)
C10	0.0243 (5)	0.0198 (5)	0.0200 (5)	0.0003 (4)	0.0067 (4)	−0.0009 (4)
C11	0.0265 (6)	0.0282 (6)	0.0276 (6)	0.0002 (5)	0.0043 (5)	−0.0051 (5)
N12	0.0238 (5)	0.0212 (5)	0.0245 (5)	0.0040 (4)	0.0080 (4)	0.0037 (4)
O13	0.0340 (5)	0.0365 (5)	0.0279 (5)	−0.0001 (4)	0.0154 (4)	0.0069 (4)
O14	0.0417 (6)	0.0349 (5)	0.0318 (5)	−0.0141 (4)	0.0084 (4)	−0.0049 (4)

C1—O2	1.4578 (15)	C7—N8	1.3178 (15)
C1—H1A	0.98	C7—C11	1.4869 (16)
C1—H1B	0.98	N8—C9	1.3682 (15)
C1—H1C	0.98	C9—C10	1.3607 (15)
O2—C3	1.3299 (13)	C9—N12	1.4329 (14)
C3—O4	1.2036 (13)	C10—H10	0.95
C3—C5	1.5183 (16)	C11—H11A	0.98
C5—N6	1.4564 (14)	C11—H11B	0.98
C5—H5A	0.99	C11—H11C	0.98
C5—H5B	0.99	N12—O13	1.2287 (12)
N6—C10	1.3641 (15)	N12—O14	1.2302 (13)
N6—C7	1.3760 (14)
O2—C1—H1A	109.5	N8—C7—N6	111.22 (10)
O2—C1—H1B	109.5	N8—C7—C11	125.81 (10)
H1A—C1—H1B	109.5	N6—C7—C11	122.96 (10)
O2—C1—H1C	109.5	C7—N8—C9	103.89 (9)
H1A—C1—H1C	109.5	C10—C9—N8	113.02 (10)
H1B—C1—H1C	109.5	C10—C9—N12	125.50 (10)
C3—O2—C1	114.24 (9)	N8—C9—N12	121.46 (10)
O4—C3—O2	124.82 (11)	C9—C10—N6	103.85 (10)
O4—C3—C5	123.76 (10)	C9—C10—H10	128.1
O2—C3—C5	111.41 (9)	N6—C10—H10	128.1
N6—C5—C3	109.20 (9)	C7—C11—H11A	109.5
N6—C5—H5A	109.8	C7—C11—H11B	109.5
C3—C5—H5A	109.8	H11A—C11—H11B	109.5
N6—C5—H5B	109.8	C7—C11—H11C	109.5
C3—C5—H5B	109.8	H11A—C11—H11C	109.5
H5A—C5—H5B	108.3	H11B—C11—H11C	109.5
C10—N6—C7	108.01 (9)	O13—N12—O14	123.54 (10)
C10—N6—C5	124.16 (9)	O13—N12—C9	118.87 (10)
C7—N6—C5	126.63 (10)	O14—N12—C9	117.58 (9)
C1—O2—C3—O4	4.91 (17)	C11—C7—N8—C9	−178.43 (10)
C1—O2—C3—C5	−175.23 (10)	C7—N8—C9—C10	−0.55 (12)
O4—C3—C5—N6	−15.79 (15)	C7—N8—C9—N12	178.05 (9)
O2—C3—C5—N6	164.35 (9)	N8—C9—C10—N6	−0.03 (12)
C3—C5—N6—C10	−86.81 (12)	N12—C9—C10—N6	−178.57 (10)
C3—C5—N6—C7	79.17 (13)	C7—N6—C10—C9	0.58 (12)
C10—N6—C7—N8	−0.99 (12)	C5—N6—C10—C9	168.78 (10)
C5—N6—C7—N8	−168.81 (10)	C10—C9—N12—O13	176.38 (10)
C10—N6—C7—C11	178.38 (10)	N8—C9—N12—O13	−2.04 (15)
C5—N6—C7—C11	10.55 (16)	C10—C9—N12—O14	−2.92 (16)
N6—C7—N8—C9	0.92 (11)	N8—C9—N12—O14	178.66 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5A···O4i	0.99	2.30	3.2350 (16)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O4i	0.99	2.30	3.2350 (16)	156

Symmetry code: (i) .