1-(2-Methyl-5-nitro-1H-imidazol-1-yl)acetone.

In the mol-ecule of the title compound, C7H9N3O3, the nitro and carbonyl groups are tilted with respect to the imidazole ring by 9.16 (6) and 65.47 (7)°, respectively. Neighbouring chains are linked via C-H⋯N and C-H⋯O hydrogen bonds forming two-dimensional slab-like networks lying parallel to (01-1).

Related literature

For the anti­biotic properties of metronidazole and mecnidazole, see: Lin et al. (2012 ▶); Almirall et al. (2011 ▶); Zhang et al. (2011 ▶). For the crystal structure of related imidazoles, see: Yousuf et al. (2012 ▶); Zeb et al. (2012 ▶).

Experimental

Crystal data

C7H9N3O3

M = 183.17

Monoclinic,

a = 4.7548 (4) Å

b = 12.3971 (9) Å

c = 14.8580 (11) Å

β = 97.350 (2)°

V = 868.62 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 273 K

0.52 × 0.33 × 0.24 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.944, T max = 0.974

5030 measured reflections

1614 independent reflections

1328 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.122

S = 1.06

1614 reflections

120 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813006569/rz5048sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006569/rz5048Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006569/rz5048Isup3.cml

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

C7H9N3O3	F(000) = 384
Mr = 183.17	Dx = 1.401 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1790 reflections
a = 4.7548 (4) Å	θ = 2.8–26.7°
b = 12.3971 (9) Å	µ = 0.11 mm−1
c = 14.8580 (11) Å	T = 273 K
β = 97.350 (2)°	Block, colorless
V = 868.62 (12) Å3	0.52 × 0.33 × 0.24 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	1614 independent reflections
Radiation source: fine-focus sealed tube	1328 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.019
ω scan	θmax = 25.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −5→5
Tmin = 0.944, Tmax = 0.974	k = −14→15
5030 measured reflections	l = −14→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0591P)2 + 0.2124P] where P = (Fo2 + 2Fc2)/3
1614 reflections	(Δ/σ)max < 0.001
120 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.15 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	−0.1621 (4)	0.29596 (12)	0.33611 (13)	0.0887 (5)
O2	0.1562 (3)	0.37418 (11)	0.26792 (12)	0.0791 (5)
O3	−0.2465 (3)	0.53369 (11)	0.15962 (9)	0.0622 (4)
N1	−0.0008 (3)	0.57463 (11)	0.33181 (9)	0.0424 (4)
N2	−0.2805 (3)	0.59824 (13)	0.43940 (10)	0.0574 (4)
N3	−0.0337 (3)	0.37691 (12)	0.31638 (12)	0.0589 (4)
C1	−0.1098 (3)	0.47575 (13)	0.35252 (12)	0.0464 (4)
C2	−0.2784 (4)	0.49243 (16)	0.41793 (12)	0.0554 (5)
H2B	−0.3781	0.4389	0.4442	0.067*
C3	−0.1137 (4)	0.64611 (14)	0.38648 (11)	0.0485 (4)
C4	−0.0467 (5)	0.76284 (16)	0.38973 (15)	0.0728 (6)
H4A	−0.1214	0.7951	0.4404	0.109*
H4B	−0.1305	0.7965	0.3346	0.109*
H4C	0.1552	0.7725	0.3963	0.109*
C5	0.1509 (3)	0.60187 (13)	0.25566 (11)	0.0444 (4)
H5A	0.3240	0.5598	0.2597	0.053*
H5B	0.2034	0.6775	0.2595	0.053*
C6	−0.0235 (3)	0.58087 (13)	0.16507 (12)	0.0451 (4)
C7	0.1011 (4)	0.62131 (17)	0.08469 (13)	0.0653 (5)
H7A	−0.0270	0.6069	0.0307	0.098*
H7B	0.2783	0.5855	0.0810	0.098*
H7C	0.1326	0.6976	0.0905	0.098*

	U11	U22	U33	U12	U13	U23
O1	0.1009 (12)	0.0431 (8)	0.1246 (15)	−0.0117 (8)	0.0248 (10)	0.0121 (8)
O2	0.0790 (10)	0.0538 (9)	0.1115 (13)	0.0122 (7)	0.0387 (9)	−0.0036 (8)
O3	0.0539 (8)	0.0678 (9)	0.0641 (9)	−0.0109 (6)	0.0049 (6)	−0.0016 (6)
N1	0.0423 (7)	0.0430 (8)	0.0437 (8)	−0.0021 (6)	0.0123 (6)	0.0018 (6)
N2	0.0622 (9)	0.0651 (10)	0.0487 (9)	−0.0007 (7)	0.0216 (7)	0.0031 (7)
N3	0.0590 (9)	0.0430 (9)	0.0751 (11)	0.0029 (7)	0.0098 (8)	0.0065 (7)
C1	0.0465 (9)	0.0426 (9)	0.0509 (10)	−0.0010 (7)	0.0098 (7)	0.0075 (7)
C2	0.0541 (10)	0.0610 (12)	0.0530 (11)	−0.0045 (9)	0.0138 (8)	0.0145 (9)
C3	0.0529 (9)	0.0508 (10)	0.0432 (9)	−0.0007 (8)	0.0112 (8)	−0.0011 (7)
C4	0.0993 (16)	0.0555 (12)	0.0684 (14)	−0.0068 (11)	0.0296 (12)	−0.0125 (10)
C5	0.0436 (8)	0.0444 (9)	0.0479 (9)	−0.0045 (7)	0.0159 (7)	0.0003 (7)
C6	0.0457 (9)	0.0395 (9)	0.0518 (10)	0.0047 (7)	0.0124 (7)	−0.0012 (7)
C7	0.0693 (12)	0.0784 (14)	0.0502 (11)	−0.0027 (10)	0.0151 (9)	0.0038 (10)

O1—N3	1.230 (2)	C3—C4	1.481 (3)
O2—N3	1.225 (2)	C4—H4A	0.9600
O3—C6	1.205 (2)	C4—H4B	0.9600
N1—C3	1.358 (2)	C4—H4C	0.9600
N1—C1	1.381 (2)	C5—C6	1.510 (2)
N1—C5	1.457 (2)	C5—H5A	0.9700
N2—C3	1.326 (2)	C5—H5B	0.9700
N2—C2	1.350 (3)	C6—C7	1.486 (3)
N3—C1	1.404 (2)	C7—H7A	0.9600
C1—C2	1.352 (2)	C7—H7B	0.9600
C2—H2B	0.9300	C7—H7C	0.9600
C3—N1—C1	104.93 (14)	C3—C4—H4C	109.5
C3—N1—C5	125.87 (14)	H4A—C4—H4C	109.5
C1—N1—C5	128.02 (14)	H4B—C4—H4C	109.5
C3—N2—C2	105.74 (15)	N1—C5—C6	112.47 (13)
O2—N3—O1	122.92 (17)	N1—C5—H5A	109.1
O2—N3—C1	119.63 (15)	C6—C5—H5A	109.1
O1—N3—C1	117.45 (17)	N1—C5—H5B	109.1
C2—C1—N1	107.35 (15)	C6—C5—H5B	109.1
C2—C1—N3	127.87 (16)	H5A—C5—H5B	107.8
N1—C1—N3	124.56 (15)	O3—C6—C7	123.21 (16)
N2—C2—C1	109.97 (15)	O3—C6—C5	121.44 (15)
N2—C2—H2B	125.0	C7—C6—C5	115.35 (14)
C1—C2—H2B	125.0	C6—C7—H7A	109.5
N2—C3—N1	112.01 (16)	C6—C7—H7B	109.5
N2—C3—C4	124.07 (16)	H7A—C7—H7B	109.5
N1—C3—C4	123.86 (16)	C6—C7—H7C	109.5
C3—C4—H4A	109.5	H7A—C7—H7C	109.5
C3—C4—H4B	109.5	H7B—C7—H7C	109.5
H4A—C4—H4B	109.5
C3—N1—C1—C2	−0.39 (18)	C2—N2—C3—N1	−0.6 (2)
C5—N1—C1—C2	−168.41 (15)	C2—N2—C3—C4	−177.73 (19)
C3—N1—C1—N3	−175.31 (16)	C1—N1—C3—N2	0.60 (18)
C5—N1—C1—N3	16.7 (3)	C5—N1—C3—N2	168.96 (14)
O2—N3—C1—C2	−168.38 (18)	C1—N1—C3—C4	177.77 (18)
O1—N3—C1—C2	11.0 (3)	C5—N1—C3—C4	−13.9 (3)
O2—N3—C1—N1	5.5 (3)	C3—N1—C5—C6	−106.10 (18)
O1—N3—C1—N1	−175.14 (16)	C1—N1—C5—C6	59.6 (2)
C3—N2—C2—C1	0.3 (2)	N1—C5—C6—O3	−9.0 (2)
N1—C1—C2—N2	0.1 (2)	N1—C5—C6—C7	171.59 (15)
N3—C1—C2—N2	174.76 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···N2i	0.93	2.56	3.361 (2)	144
C5—H5B···O2ii	0.97	2.57	3.527 (2)	167
C7—H7B···O3iii	0.96	2.49	3.340 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯N2i	0.93	2.56	3.361 (2)	144
C5—H5B⋯O2ii	0.97	2.57	3.527 (2)	167
C7—H7B⋯O3iii	0.96	2.49	3.340 (2)	147

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