2-Chloro-4-nitro-1H-imidazole.

The mol-ecule of the title compound, C(3)H(2)ClN(3)O(2), is almost planar; the dihedral angle between the imidazole ring and the nitro group is 1.7 (2)°. In the crystal structure, pairs of inter-molecular C-H⋯O hydrogen bonds link inversion-related mol-ecules into dimers, generating R(2) (2)(10) ring motifs. The dimers are inter-connected into two-dimensional networks parallel to (102) via inter-molecular N-H⋯N hydrogen bonds. Further stabilization is provided by short inter-molecular Cl⋯O inter-actions [3.142 (2) and 3.1475 (19) Å].

Related literature

For general background to and applications of imidazole derivatives, see: Anuradha et al. (2006 ▶); Clark & Macquarrie (1996 ▶); Jadhav et al. (2008 ▶); Kolavi et al. (2006 ▶); Susanta et al. (2000 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For related 4-nitro­imidazole crystal structures, see: Ségalas et al. (1992 ▶); De Bondt et al. (1993 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C3H2ClN3O2

M = 147.53

Monoclinic,

a = 5.905 (2) Å

b = 10.033 (4) Å

c = 9.150 (3) Å

β = 105.180 (8)°

V = 523.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.64 mm−1

T = 100 K

0.29 × 0.19 × 0.04 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.837, T max = 0.977

5484 measured reflections

1509 independent reflections

1195 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.097

S = 1.11

1509 reflections

90 parameters

All H-atom parameters refined

Δρmax = 0.42 e Å−3

Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024542/ci5106sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024542/ci5106Isup2.hkl

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

C3H2ClN3O2	F(000) = 296
Mr = 147.53	Dx = 1.873 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2073 reflections
a = 5.905 (2) Å	θ = 3.6–30.0°
b = 10.033 (4) Å	µ = 0.64 mm−1
c = 9.150 (3) Å	T = 100 K
β = 105.180 (8)°	Plate, yellow
V = 523.2 (3) Å3	0.29 × 0.19 × 0.04 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	1509 independent reflections
Radiation source: fine-focus sealed tube	1195 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 30.0°, θmin = 3.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→8
Tmin = 0.837, Tmax = 0.977	k = −13→14
5484 measured reflections	l = −12→12

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	All H-atom parameters refined
S = 1.11	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.1822P] where P = (Fo2 + 2Fc2)/3
1509 reflections	(Δ/σ)max = 0.001
90 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Cl1	0.72178 (8)	0.63986 (4)	0.10842 (5)	0.01869 (15)
O1	0.0169 (3)	0.65199 (14)	0.47907 (19)	0.0268 (4)
O2	0.1231 (3)	0.84048 (13)	0.40048 (18)	0.0250 (3)
N1	0.4713 (3)	0.49414 (15)	0.25596 (19)	0.0157 (3)
N2	0.4212 (3)	0.71387 (14)	0.26450 (18)	0.0151 (3)
N3	0.1318 (3)	0.71851 (16)	0.41138 (19)	0.0190 (3)
C1	0.5304 (3)	0.61677 (16)	0.2149 (2)	0.0149 (4)
C2	0.3104 (3)	0.51281 (17)	0.3371 (2)	0.0164 (4)
C3	0.2845 (3)	0.64762 (17)	0.3405 (2)	0.0150 (4)
H1N1	0.525 (4)	0.417 (3)	0.240 (3)	0.025 (6)*
H2	0.246 (4)	0.441 (3)	0.375 (3)	0.025 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0218 (2)	0.0162 (2)	0.0214 (3)	−0.00093 (16)	0.01140 (19)	0.00052 (17)
O1	0.0311 (8)	0.0228 (7)	0.0340 (9)	−0.0028 (6)	0.0221 (7)	−0.0015 (6)
O2	0.0308 (8)	0.0120 (6)	0.0351 (9)	0.0043 (5)	0.0140 (7)	−0.0022 (6)
N1	0.0193 (8)	0.0096 (7)	0.0196 (8)	0.0010 (6)	0.0078 (7)	−0.0003 (6)
N2	0.0179 (8)	0.0107 (6)	0.0184 (8)	0.0001 (5)	0.0075 (6)	0.0000 (6)
N3	0.0206 (8)	0.0151 (7)	0.0231 (9)	0.0008 (6)	0.0090 (7)	−0.0017 (6)
C1	0.0174 (9)	0.0113 (8)	0.0163 (9)	−0.0013 (6)	0.0053 (7)	−0.0004 (6)
C2	0.0186 (9)	0.0114 (8)	0.0208 (10)	−0.0010 (6)	0.0082 (8)	0.0001 (7)
C3	0.0167 (9)	0.0122 (8)	0.0170 (9)	−0.0007 (6)	0.0060 (7)	−0.0019 (7)

Cl1—C1	1.690 (2)	N2—C1	1.313 (2)
O1—N3	1.228 (2)	N2—C3	1.368 (2)
O2—N3	1.228 (2)	N3—C3	1.430 (2)
N1—C1	1.359 (2)	C2—C3	1.362 (2)
N1—C2	1.363 (3)	C2—H2	0.93 (3)
N1—H1N1	0.86 (3)
C1—N1—C2	107.01 (15)	N2—C1—Cl1	124.11 (14)
C1—N1—H1N1	129.2 (17)	N1—C1—Cl1	122.87 (14)
C2—N1—H1N1	123.7 (17)	C3—C2—N1	104.32 (16)
C1—N2—C3	102.95 (15)	C3—C2—H2	135.0 (16)
O2—N3—O1	124.46 (17)	N1—C2—H2	120.7 (16)
O2—N3—C3	118.46 (16)	C2—C3—N2	112.71 (17)
O1—N3—C3	117.08 (16)	C2—C3—N3	126.29 (18)
N2—C1—N1	113.01 (17)	N2—C3—N3	120.99 (16)
C3—N2—C1—N1	−0.4 (2)	C1—N2—C3—C2	0.0 (2)
C3—N2—C1—Cl1	178.70 (15)	C1—N2—C3—N3	−179.05 (17)
C2—N1—C1—N2	0.6 (2)	O2—N3—C3—C2	−177.8 (2)
C2—N1—C1—Cl1	−178.52 (14)	O1—N3—C3—C2	1.9 (3)
C1—N1—C2—C3	−0.5 (2)	O2—N3—C3—N2	1.1 (3)
N1—C2—C3—N2	0.3 (2)	O1—N3—C3—N2	−179.10 (18)
N1—C2—C3—N3	179.32 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2i	0.86 (3)	2.07 (3)	2.900 (2)	163 (2)
C2—H2···O1ii	0.92 (3)	2.48 (3)	3.317 (3)	151 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2i	0.86 (3)	2.07 (3)	2.900 (2)	163 (2)
C2—H2⋯O1ii	0.92 (3)	2.48 (3)	3.317 (3)	151 (2)

Symmetry codes: (i) ; (ii) .