2-(2-Methyl-5-nitro-1H-imidazol-1-yl)ethyl N-methyl-carbamate.

In the title compound, C(8)H(12)N(4)O(4), the essentially planar methyl-carbamoyloxymethyl group [maximum deviation 0.038 (3) Å] and the imidazole ring make a dihedral angle of 48.47 (3)°. The crystal packing is stabilized by inter-molecular N-H⋯N and C-H⋯O hydrogen bonds, which link the mol-ecules into infinite ribbons running along the a axis, and by weak π-π stacking inter-actions [centroid-centroid distance = 3.894 (2) Å].

Related literature

For biological activity, see: Cina et al. (1996 ▶); Karamanakos et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H12N4O4

M = 228.22

Monoclinic,

a = 9.6959 (12) Å

b = 7.2898 (9) Å

c = 15.589 (2) Å

β = 101.400 (2)°

V = 1080.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 273 (2) K

0.15 × 0.12 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

5515 measured reflections

1921 independent reflections

1622 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.089

S = 1.05

1921 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808041676/hg2452sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808041676/hg2452Isup2.hkl

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

C8H12N4O4	F(000) = 480
Mr = 228.22	Dx = 1.403 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2505 reflections
a = 9.6959 (12) Å	θ = 2.7–27.1°
b = 7.2898 (9) Å	µ = 0.11 mm−1
c = 15.589 (2) Å	T = 273 K
β = 101.400 (2)°	Block, yellow
V = 1080.1 (2) Å3	0.15 × 0.12 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1622 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.015
graphite	θmax = 25.0°, θmin = 2.3°
φ and ω scans	h = −11→11
5515 measured reflections	k = −8→8
1921 independent reflections	l = −9→18

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031	H-atom parameters constrained
wR(F2) = 0.089	w = 1/[σ2(Fo2) + (0.0404P)2 + 0.2462P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
1921 reflections	Δρmax = 0.19 e Å−3
146 parameters	Δρmin = −0.14 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

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	0.41899 (13)	0.31179 (19)	0.60227 (7)	0.0673 (4)
O2	0.62309 (12)	0.35345 (19)	0.56977 (8)	0.0693 (4)
O3	0.06913 (10)	0.38773 (15)	0.39251 (7)	0.0495 (3)
O4	−0.13394 (10)	0.24805 (16)	0.40569 (7)	0.0516 (3)
N1	0.45446 (13)	0.11166 (19)	0.33518 (8)	0.0511 (3)
N2	0.32310 (11)	0.14897 (15)	0.43564 (7)	0.0368 (3)
N3	0.50075 (13)	0.29867 (17)	0.55195 (8)	0.0461 (3)
N4	−0.11627 (13)	0.41147 (18)	0.28483 (8)	0.0489 (3)
H4	−0.0602	0.4739	0.2598	0.059*
C1	0.45604 (14)	0.21818 (18)	0.46825 (9)	0.0374 (3)
C2	0.53355 (15)	0.1938 (2)	0.40604 (10)	0.0456 (4)
H2	0.6272	0.2283	0.4111	0.055*
C3	0.32821 (15)	0.0863 (2)	0.35445 (9)	0.0437 (4)
C4	0.20850 (19)	−0.0011 (3)	0.29424 (12)	0.0657 (5)
H4A	0.2356	−0.0287	0.2397	0.099*
H4B	0.1297	0.0812	0.2841	0.099*
H4C	0.1828	−0.1125	0.3200	0.099*
C5	0.20058 (15)	0.1428 (2)	0.47777 (10)	0.0453 (4)
H5A	0.2301	0.0991	0.5373	0.054*
H5B	0.1326	0.0562	0.4467	0.054*
C6	0.13134 (15)	0.3268 (2)	0.47920 (10)	0.0489 (4)
H6A	0.0591	0.3191	0.5141	0.059*
H6B	0.2007	0.4159	0.5064	0.059*
C7	−0.06789 (14)	0.34081 (19)	0.36319 (9)	0.0390 (3)
C8	−0.26021 (17)	0.3868 (2)	0.24023 (11)	0.0564 (4)
H8A	−0.2734	0.2632	0.2190	0.085*
H8B	−0.2811	0.4705	0.1918	0.085*
H8C	−0.3219	0.4104	0.2801	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.0660 (8)	0.0934 (10)	0.0442 (6)	−0.0052 (7)	0.0153 (6)	−0.0090 (6)
O2	0.0506 (7)	0.0844 (9)	0.0671 (8)	−0.0186 (6)	−0.0026 (6)	−0.0062 (7)
O3	0.0351 (5)	0.0590 (7)	0.0568 (7)	−0.0004 (5)	0.0146 (5)	0.0064 (5)
O4	0.0431 (6)	0.0645 (7)	0.0486 (6)	−0.0100 (5)	0.0123 (5)	0.0118 (5)
N1	0.0494 (7)	0.0567 (8)	0.0504 (8)	0.0087 (6)	0.0176 (6)	−0.0046 (6)
N2	0.0346 (6)	0.0373 (6)	0.0394 (6)	0.0021 (5)	0.0091 (5)	0.0027 (5)
N3	0.0447 (7)	0.0477 (7)	0.0436 (7)	−0.0008 (6)	0.0029 (6)	0.0050 (6)
N4	0.0441 (7)	0.0564 (8)	0.0491 (7)	−0.0010 (6)	0.0162 (6)	0.0130 (6)
C1	0.0350 (7)	0.0356 (7)	0.0410 (7)	0.0018 (6)	0.0062 (6)	0.0040 (6)
C2	0.0364 (8)	0.0477 (8)	0.0547 (9)	0.0043 (6)	0.0141 (7)	0.0042 (7)
C3	0.0459 (8)	0.0405 (8)	0.0439 (8)	0.0073 (6)	0.0071 (6)	−0.0020 (6)
C4	0.0633 (11)	0.0710 (12)	0.0582 (10)	−0.0002 (9)	0.0007 (8)	−0.0172 (9)
C5	0.0378 (7)	0.0522 (9)	0.0481 (8)	−0.0052 (6)	0.0138 (6)	0.0045 (7)
C6	0.0361 (8)	0.0641 (10)	0.0478 (9)	0.0024 (7)	0.0112 (6)	−0.0061 (7)
C7	0.0359 (7)	0.0385 (7)	0.0460 (8)	0.0023 (6)	0.0162 (6)	−0.0017 (6)
C8	0.0554 (10)	0.0609 (10)	0.0512 (9)	−0.0011 (8)	0.0062 (7)	0.0107 (8)

O1—N3	1.2241 (16)	C1—C2	1.3509 (19)
O2—N3	1.2303 (16)	C2—H2	0.9300
O3—C7	1.3605 (17)	C3—C4	1.485 (2)
O3—C6	1.4370 (18)	C4—H4A	0.9600
O4—C7	1.2140 (16)	C4—H4B	0.9600
N1—C3	1.3297 (19)	C4—H4C	0.9600
N1—C2	1.354 (2)	C5—C6	1.503 (2)
N2—C3	1.3555 (18)	C5—H5A	0.9700
N2—C1	1.3840 (17)	C5—H5B	0.9700
N2—C5	1.4673 (17)	C6—H6A	0.9700
N3—C1	1.4181 (18)	C6—H6B	0.9700
N4—C7	1.3233 (19)	C8—H8A	0.9600
N4—C8	1.442 (2)	C8—H8B	0.9600
N4—H4	0.8600	C8—H8C	0.9600
C7—O3—C6	116.02 (11)	H4A—C4—H4C	109.5
C3—N1—C2	105.99 (12)	H4B—C4—H4C	109.5
C3—N2—C1	105.22 (11)	N2—C5—C6	112.52 (12)
C3—N2—C5	126.14 (12)	N2—C5—H5A	109.1
C1—N2—C5	128.64 (11)	C6—C5—H5A	109.1
O1—N3—O2	123.20 (13)	N2—C5—H5B	109.1
O1—N3—C1	120.20 (12)	C6—C5—H5B	109.1
O2—N3—C1	116.60 (13)	H5A—C5—H5B	107.8
C7—N4—C8	121.95 (12)	O3—C6—C5	111.56 (12)
C7—N4—H4	119.0	O3—C6—H6A	109.3
C8—N4—H4	119.0	C5—C6—H6A	109.3
C2—C1—N2	107.35 (12)	O3—C6—H6B	109.3
C2—C1—N3	127.06 (13)	C5—C6—H6B	109.3
N2—C1—N3	125.59 (12)	H6A—C6—H6B	108.0
C1—C2—N1	109.76 (13)	O4—C7—N4	126.27 (13)
C1—C2—H2	125.1	O4—C7—O3	122.83 (13)
N1—C2—H2	125.1	N4—C7—O3	110.89 (12)
N1—C3—N2	111.67 (13)	N4—C8—H8A	109.5
N1—C3—C4	123.81 (14)	N4—C8—H8B	109.5
N2—C3—C4	124.52 (14)	H8A—C8—H8B	109.5
C3—C4—H4A	109.5	N4—C8—H8C	109.5
C3—C4—H4B	109.5	H8A—C8—H8C	109.5
H4A—C4—H4B	109.5	H8B—C8—H8C	109.5
C3—C4—H4C	109.5
C3—N2—C1—C2	−0.11 (15)	C1—N2—C3—N1	0.19 (16)
C5—N2—C1—C2	−179.97 (13)	C5—N2—C3—N1	−179.95 (13)
C3—N2—C1—N3	−179.87 (13)	C1—N2—C3—C4	179.78 (15)
C5—N2—C1—N3	0.3 (2)	C5—N2—C3—C4	−0.4 (2)
O1—N3—C1—C2	−179.83 (15)	C3—N2—C5—C6	−104.57 (16)
O2—N3—C1—C2	0.5 (2)	C1—N2—C5—C6	75.25 (18)
O1—N3—C1—N2	−0.1 (2)	C7—O3—C6—C5	91.29 (14)
O2—N3—C1—N2	−179.77 (13)	N2—C5—C6—O3	66.34 (16)
N2—C1—C2—N1	0.01 (16)	C8—N4—C7—O4	1.1 (2)
N3—C1—C2—N1	179.76 (13)	C8—N4—C7—O3	−178.06 (13)
C3—N1—C2—C1	0.11 (17)	C6—O3—C7—O4	−2.3 (2)
C2—N1—C3—N2	−0.19 (17)	C6—O3—C7—N4	176.83 (12)
C2—N1—C3—C4	−179.78 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···N1i	0.86	2.20	3.0416 (17)	165
C2—H2···O4ii	0.93	2.34	3.2492 (18)	166
C8—H8B···O4iii	0.96	2.57	3.498 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯N1i	0.86	2.20	3.0416 (17)	165
C2—H2⋯O4ii	0.93	2.34	3.2492 (18)	166
C8—H8B⋯O4iii	0.96	2.57	3.498 (2)	164

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