1-(3-Chloro-phen-yl)-2-methyl-4-nitro-1H-imidazole-5-carboxamide.

In the crystal structure of the title compound, C(11)H(9)ClN(4)O(3), pairs of N-H⋯N(imidazole) hydrogen bonds connect the mol-ecules into centrosymmetric dimers, which are further connected by N-H⋯O(carbamo-yl) hydrogen bonds into C(4) chains along [010]. Inter-play of these two kinds of hydrogen bonds connect the mol-ecules into layers perpendicular to [101]. The imidazole [maximum deviation 0.0069 (9) Å] and phenyl rings are inclined at a dihedral angle of 58.44 (6)°; the nitro group is almost coplanar [dihedral angle 5.8 (2)°] with the imidazole ring while the carbamoyl group is almost perpendicular [70.15 (13)°] to it.

Related literature

For the synthesis, see: Suwiński et al. (1994 ▶). For similar nitro­imidazole derivatives, see: Kubicki (2004a ▶,b ▶). For a recent experimental charge density study of a nitro­imidazole derivative, see: Paul et al. (2011 ▶).

Experimental

Crystal data

C11H9ClN4O3

M = 280.67

Monoclinic,

a = 21.8417 (14) Å

b = 7.3710 (4) Å

c = 16.2467 (10) Å

β = 108.680 (7)°

V = 2477.9 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.32 mm−1

T = 295 K

0.25 × 0.2 × 0.08 mm

Data collection

Agilent Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.833, T max = 1.000

4943 measured reflections

2702 independent reflections

2185 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.104

S = 1.04

2702 reflections

197 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.32 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811036609/zk2021sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811036609/zk2021Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811036609/zk2021Isup3.cml

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

C11H9ClN4O3	F(000) = 1152
Mr = 280.67	Dx = 1.505 Mg m−3
Monoclinic, Ce2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1970 reflections
a = 21.8417 (14) Å	θ = 2.6–27.8°
b = 7.3710 (4) Å	µ = 0.32 mm−1
c = 16.2467 (10) Å	T = 295 K
β = 108.680 (7)°	Plate, colourless
V = 2477.9 (3) Å3	0.25 × 0.2 × 0.08 mm
Z = 8

Agilent Xcalibur Sapphire2 diffractometer	2702 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2185 reflections with I > 2σ(I)
graphite	Rint = 0.019
Detector resolution: 8.1929 pixels mm-1	θmax = 27.9°, θmin = 2.8°
ω–scan	h = −28→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −9→9
Tmin = 0.833, Tmax = 1.000	l = −19→20
4943 measured 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0514P)2 + 1.4411P] where P = (Fo2 + 2Fc2)/3
2702 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.32 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 > 2σ(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
N1	0.17359 (6)	0.85257 (17)	0.33362 (8)	0.0271 (3)
C11	0.12098 (7)	0.8118 (2)	0.25590 (9)	0.0293 (3)
C12	0.09423 (8)	0.6397 (2)	0.24501 (11)	0.0332 (4)
H12	0.1077 (9)	0.552 (3)	0.2894 (12)	0.037 (5)*
C13	0.04732 (8)	0.6004 (2)	0.16645 (11)	0.0379 (4)
Cl13	0.01602 (3)	0.38209 (7)	0.14854 (4)	0.05910 (19)
C14	0.02578 (10)	0.7283 (3)	0.10197 (12)	0.0504 (5)
H14	−0.0065 (11)	0.699 (3)	0.0509 (15)	0.064 (7)*
C15	0.05307 (10)	0.8993 (3)	0.11556 (13)	0.0560 (6)
H15	0.0382 (12)	0.991 (4)	0.0733 (17)	0.072 (7)*
C16	0.10138 (9)	0.9419 (3)	0.19203 (12)	0.0415 (4)
H16	0.1217 (10)	1.055 (3)	0.2009 (13)	0.046 (5)*
C2	0.17800 (8)	0.9965 (2)	0.38931 (10)	0.0305 (3)
C21	0.12317 (10)	1.1186 (3)	0.38571 (14)	0.0502 (5)
H21A	0.1342	1.1920	0.4372	0.075*
H21B	0.0856	1.0473	0.3821	0.075*
H21C	0.1142	1.1955	0.3355	0.075*
N3	0.23569 (7)	1.00575 (17)	0.44768 (8)	0.0310 (3)
C4	0.26864 (7)	0.8643 (2)	0.42808 (9)	0.0266 (3)
N4	0.33550 (7)	0.83535 (19)	0.47546 (8)	0.0339 (3)
O41	0.36067 (7)	0.9295 (2)	0.53941 (9)	0.0568 (4)
O42	0.36375 (6)	0.7157 (2)	0.44992 (9)	0.0543 (4)
C5	0.23205 (7)	0.76476 (19)	0.35908 (9)	0.0249 (3)
C51	0.24424 (7)	0.5998 (2)	0.31274 (9)	0.0267 (3)
O51	0.24669 (7)	0.61445 (15)	0.23864 (7)	0.0387 (3)
N51	0.24967 (7)	0.44533 (19)	0.35555 (9)	0.0342 (3)
H51A	0.2520 (9)	0.444 (3)	0.4089 (13)	0.039 (5)*
H51B	0.2552 (9)	0.346 (3)	0.3297 (12)	0.037 (5)*

	U11	U22	U33	U12	U13	U23
N1	0.0274 (6)	0.0263 (6)	0.0261 (6)	0.0018 (5)	0.0067 (5)	−0.0005 (5)
C11	0.0257 (7)	0.0328 (8)	0.0273 (7)	0.0001 (6)	0.0054 (6)	−0.0001 (6)
C12	0.0332 (8)	0.0334 (8)	0.0308 (8)	−0.0010 (7)	0.0071 (7)	0.0005 (7)
C13	0.0336 (9)	0.0394 (9)	0.0379 (9)	−0.0081 (7)	0.0073 (7)	−0.0065 (7)
Cl13	0.0610 (3)	0.0487 (3)	0.0575 (3)	−0.0197 (2)	0.0048 (3)	−0.0114 (2)
C14	0.0399 (10)	0.0630 (13)	0.0362 (10)	−0.0071 (9)	−0.0046 (8)	0.0027 (9)
C15	0.0496 (12)	0.0587 (13)	0.0426 (10)	−0.0043 (10)	−0.0093 (9)	0.0181 (10)
C16	0.0367 (9)	0.0388 (10)	0.0409 (9)	−0.0040 (8)	0.0012 (7)	0.0092 (8)
C2	0.0370 (8)	0.0255 (7)	0.0299 (7)	0.0026 (6)	0.0118 (6)	−0.0003 (6)
C21	0.0482 (11)	0.0447 (11)	0.0579 (12)	0.0155 (9)	0.0174 (9)	−0.0052 (9)
N3	0.0387 (7)	0.0269 (7)	0.0272 (6)	0.0012 (6)	0.0103 (6)	−0.0035 (5)
C4	0.0303 (8)	0.0266 (7)	0.0215 (6)	0.0000 (6)	0.0066 (6)	0.0000 (6)
N4	0.0332 (7)	0.0368 (7)	0.0279 (6)	−0.0020 (6)	0.0045 (6)	−0.0023 (6)
O41	0.0461 (8)	0.0674 (9)	0.0430 (7)	−0.0046 (7)	−0.0050 (6)	−0.0219 (7)
O42	0.0351 (7)	0.0607 (9)	0.0597 (8)	0.0109 (6)	0.0049 (6)	−0.0182 (7)
C5	0.0278 (7)	0.0243 (7)	0.0219 (6)	0.0008 (6)	0.0071 (6)	0.0016 (5)
C51	0.0283 (7)	0.0257 (7)	0.0245 (7)	0.0003 (6)	0.0062 (6)	−0.0027 (6)
O51	0.0627 (8)	0.0305 (6)	0.0268 (6)	0.0056 (6)	0.0196 (5)	0.0008 (5)
N51	0.0530 (9)	0.0239 (7)	0.0266 (7)	0.0029 (6)	0.0142 (6)	−0.0014 (6)

N1—C5	1.3719 (19)	C2—C21	1.484 (2)
N1—C2	1.3774 (19)	C21—H21A	0.9600
N1—C11	1.4408 (19)	C21—H21B	0.9600
C11—C16	1.377 (2)	C21—H21C	0.9600
C11—C12	1.384 (2)	N3—C4	1.361 (2)
C12—C13	1.388 (2)	C4—C5	1.364 (2)
C12—H12	0.94 (2)	C4—N4	1.432 (2)
C13—C14	1.376 (3)	N4—O42	1.2228 (19)
C13—Cl13	1.7360 (18)	N4—O41	1.2236 (18)
C14—C15	1.381 (3)	C5—C51	1.498 (2)
C14—H14	0.93 (2)	C51—O51	1.2270 (18)
C15—C16	1.384 (3)	C51—N51	1.319 (2)
C15—H15	0.94 (3)	N51—H51A	0.85 (2)
C16—H16	0.93 (2)	N51—H51B	0.87 (2)
C2—N3	1.314 (2)
C5—N1—C2	107.62 (12)	N1—C2—C21	123.73 (15)
C5—N1—C11	124.74 (12)	C2—C21—H21A	109.5
C2—N1—C11	127.22 (13)	C2—C21—H21B	109.5
C16—C11—C12	121.72 (15)	H21A—C21—H21B	109.5
C16—C11—N1	118.89 (15)	C2—C21—H21C	109.5
C12—C11—N1	119.27 (14)	H21A—C21—H21C	109.5
C11—C12—C13	117.78 (15)	H21B—C21—H21C	109.5
C11—C12—H12	121.0 (11)	C2—N3—C4	104.35 (13)
C13—C12—H12	121.2 (11)	N3—C4—C5	112.95 (14)
C14—C13—C12	121.94 (17)	N3—C4—N4	120.85 (13)
C14—C13—Cl13	119.18 (14)	C5—C4—N4	126.15 (14)
C12—C13—Cl13	118.87 (14)	O42—N4—O41	123.99 (15)
C13—C14—C15	118.62 (17)	O42—N4—C4	117.62 (13)
C13—C14—H14	119.8 (15)	O41—N4—C4	118.38 (14)
C15—C14—H14	121.6 (15)	C4—C5—N1	103.76 (13)
C14—C15—C16	121.11 (18)	C4—C5—C51	134.27 (14)
C14—C15—H15	120.4 (15)	N1—C5—C51	121.97 (13)
C16—C15—H15	118.5 (15)	O51—C51—N51	124.64 (14)
C11—C16—C15	118.79 (18)	O51—C51—C5	119.48 (13)
C11—C16—H16	119.2 (13)	N51—C51—C5	115.84 (13)
C15—C16—H16	122.0 (12)	C51—N51—H51A	121.0 (14)
N3—C2—N1	111.31 (14)	C51—N51—H51B	118.4 (12)
N3—C2—C21	124.90 (15)	H51A—N51—H51B	120.2 (19)
C5—N1—C11—C16	−115.99 (18)	C21—C2—N3—C4	177.36 (16)
C2—N1—C11—C16	55.6 (2)	C2—N3—C4—C5	−0.99 (17)
C5—N1—C11—C12	60.0 (2)	C2—N3—C4—N4	176.64 (14)
C2—N1—C11—C12	−128.44 (17)	N3—C4—N4—O42	−173.81 (15)
C16—C11—C12—C13	1.1 (3)	C5—C4—N4—O42	3.5 (2)
N1—C11—C12—C13	−174.80 (15)	N3—C4—N4—O41	7.2 (2)
C11—C12—C13—C14	−2.3 (3)	C5—C4—N4—O41	−175.54 (15)
C11—C12—C13—Cl13	176.52 (12)	N3—C4—C5—N1	1.33 (17)
C12—C13—C14—C15	1.6 (3)	N4—C4—C5—N1	−176.15 (14)
Cl13—C13—C14—C15	−177.23 (17)	N3—C4—C5—C51	−179.51 (15)
C13—C14—C15—C16	0.4 (3)	N4—C4—C5—C51	3.0 (3)
C12—C11—C16—C15	0.8 (3)	C2—N1—C5—C4	−1.11 (15)
N1—C11—C16—C15	176.73 (17)	C11—N1—C5—C4	171.84 (13)
C14—C15—C16—C11	−1.6 (3)	C2—N1—C5—C51	179.59 (13)
C5—N1—C2—N3	0.58 (17)	C11—N1—C5—C51	−7.5 (2)
C11—N1—C2—N3	−172.15 (14)	C4—C5—C51—O51	−110.4 (2)
C5—N1—C2—C21	−176.59 (16)	N1—C5—C51—O51	68.6 (2)
C11—N1—C2—C21	10.7 (2)	C4—C5—C51—N51	71.6 (2)
N1—C2—N3—C4	0.23 (17)	N1—C5—C51—N51	−109.36 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N51—H51A···N3i	0.85 (2)	2.29 (2)	3.130 (2)	169.2 (18)
N51—H51B···O51ii	0.87 (2)	2.03 (2)	2.8938 (19)	171.3 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N51—H51A⋯N3i	0.85 (2)	2.29 (2)	3.130 (2)	169.2 (18)
N51—H51B⋯O51ii	0.87 (2)	2.03 (2)	2.8938 (19)	171.3 (18)

Symmetry codes: (i) ; (ii) .