Crystal structure of (E)-1-methyl-2-[2-(2-methoxphen-yl)ethen-yl]-4-nitro-1H-imidazole.

In the asymmetric unit of the title compound, C13H13N3O3, the 2-(2-methoxphen-yl)ethenyl unit is connected to the methyl-nitro-imidazole 1-methyl-4-nitro-1H-imidazole moiety. The mol-ecule is quasi-planar and the planes of the two rings form a dihedral angle of 0.92 (11)°. The crystal packing can be described as layers parallel to the (011) plane, stabilized by inter-molecular C-H⋯O hydrogen bonding, resulting in the formation of an infinite three-dimensional network linking these layers. Strong π-π stacking inter-actions are observed, viz. benzene-benzene, imidazole-imidazole and benzene-imidazole rings, with centroid-centroid distances of 3.528 (2), 3.457 (2) and 3.544 (2) Å, respectively. Intensity statistics indicated twinning by non-merohedry, with refined weighs of the twin components of 0.3687:0.6313.

Related literature

For the synthesis and applications of this important class of compounds, see: Hori et al. (1997 ▶); Bourdin-Trunz et al. (2011 ▶). For our previous work on imidazole derivatives, see: Alliouche et al. (2014 ▶); Zama et al. (2013 ▶); Bahnous et al. (2012 ▶).

Experimental

Crystal data

C13H13N3O3

M = 259.26

Triclinic,

a = 7.9339 (18) Å

b = 8.1994 (19) Å

c = 10.452 (3) Å

α = 68.877 (17)°

β = 75.037 (17)°

γ = 76.182 (17)°

V = 604.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 150 K

0.19 × 0.12 × 0.08 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.754, T max = 1.000

5177 measured reflections

5177 independent reflections

3712 reflections with I > 2σ(I)

Refinement

R[F 2 > 2σ(F 2)] = 0.088

wR(F 2) = 0.282

S = 1.06

5171 reflections

176 parameters

H-atom parameters constrained

Δρmax = 0.49 e Å−3

Δρmin = −0.42 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); 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 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814017206/hg5400sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017206/hg5400Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S1600536814017206/hg5400fig1.tif

The structure of the title compound with the atomic labelling scheme. Displacement are drawn at the 50% probability level.

Click here for additional data file.

a . DOI: 10.1107/S1600536814017206/hg5400fig2.tif

A diagram of the layered crystal packing of (I) viewed down the a axis and showing hydrogen bond [C—H⋯O] as dashed line.

CCDC reference: 1015965

Additional supporting information: crystallographic information; 3D view; checkCIF report

C13H13N3O3	Z = 2
Mr = 259.26	F(000) = 272
Triclinic, P1	Dx = 1.424 Mg m−3
a = 7.9339 (18) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1994 (19) Å	Cell parameters from 1356 reflections
c = 10.452 (3) Å	θ = 2.7–24.6°
α = 68.877 (17)°	µ = 0.10 mm−1
β = 75.037 (17)°	T = 150 K
γ = 76.182 (17)°	Block, yellow
V = 604.7 (2) Å3	0.19 × 0.12 × 0.08 mm

Bruker APEXII diffractometer	3712 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0
CCD rotation images, thin slices scans	θmax = 25.3°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −9→9
Tmin = 0.754, Tmax = 1.000	k = −9→9
5177 measured reflections	l = −12→12
5177 independent reflections

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)] = 0.088	H-atom parameters constrained
wR(F2) = 0.282	w = 1/[σ2(Fo2) + (0.1745P)2 + 0.1919P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
5171 reflections	Δρmax = 0.49 e Å−3
176 parameters	Δρmin = −0.42 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.045 (12)

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	0.4178 (3)	0.2400 (3)	0.2786 (3)	0.0256 (6)
O3	1.0969 (3)	0.6148 (3)	0.0846 (2)	0.0219 (6)
O2	0.1531 (3)	0.2922 (3)	0.3961 (3)	0.0238 (6)
N1	0.3026 (4)	0.3303 (4)	0.3420 (3)	0.0167 (7)
N2	0.5059 (3)	0.5331 (4)	0.2979 (3)	0.0162 (7)
N3	0.3292 (3)	0.7076 (3)	0.4156 (3)	0.0134 (6)
C1	0.3460 (4)	0.4809 (4)	0.3545 (3)	0.0142 (7)
C2	0.4934 (4)	0.6726 (4)	0.3362 (3)	0.0125 (7)
C5	0.6299 (4)	0.7796 (5)	0.3004 (3)	0.0172 (8)
H5	0.6018	0.8867	0.319	0.021*
C6	0.7973 (4)	0.7279 (4)	0.2408 (3)	0.0151 (7)
H6	0.8198	0.6187	0.2261	0.018*
C7	0.9464 (4)	0.8227 (4)	0.1968 (3)	0.0139 (7)
C8	1.1027 (4)	0.7634 (4)	0.1144 (3)	0.0159 (8)
C13	1.2438 (4)	0.5580 (5)	−0.0106 (4)	0.0273 (9)
H13C	1.2622	0.6542	−0.0961	0.041*
H13A	1.22	0.4604	−0.0296	0.041*
H13B	1.3478	0.5214	0.0299	0.041*
C4	0.2711 (4)	0.8439 (5)	0.4845 (3)	0.0196 (8)
H4A	0.1465	0.8508	0.5215	0.029*
H4B	0.2948	0.9563	0.418	0.029*
H4C	0.3339	0.814	0.5591	0.029*
C3	0.2328 (4)	0.5873 (4)	0.4277 (3)	0.0139 (7)
H3	0.117	0.5778	0.4744	0.017*
C9	1.2469 (4)	0.8506 (5)	0.0702 (3)	0.0207 (8)
H9	1.349	0.81	0.0154	0.025*
C10	1.2392 (5)	0.9970 (5)	0.1072 (3)	0.0233 (8)
H10	1.3369	1.0544	0.0781	0.028*
C11	1.0871 (4)	1.0600 (5)	0.1876 (3)	0.0211 (8)
H11	1.0818	1.1602	0.2116	0.025*
C12	0.9434 (4)	0.9723 (5)	0.2317 (3)	0.0199 (8)
H12	0.8418	1.0144	0.2863	0.024*

	U11	U22	U33	U12	U13	U23
O1	0.0232 (13)	0.0238 (14)	0.0331 (14)	−0.0046 (11)	0.0055 (11)	−0.0199 (12)
O3	0.0169 (13)	0.0238 (14)	0.0257 (13)	−0.0036 (10)	0.0029 (10)	−0.0135 (11)
O2	0.0142 (13)	0.0280 (15)	0.0313 (14)	−0.0066 (11)	0.0037 (11)	−0.0154 (12)
N1	0.0173 (15)	0.0150 (15)	0.0183 (14)	−0.0021 (12)	−0.0013 (12)	−0.0077 (12)
N2	0.0144 (14)	0.0181 (15)	0.0159 (14)	−0.0007 (12)	−0.0022 (11)	−0.0070 (12)
N3	0.0139 (14)	0.0113 (14)	0.0162 (13)	−0.0006 (11)	−0.0005 (11)	−0.0083 (11)
C1	0.0135 (16)	0.0166 (17)	0.0122 (16)	−0.0007 (13)	−0.0053 (13)	−0.0032 (13)
C2	0.0120 (16)	0.0162 (17)	0.0099 (14)	−0.0020 (13)	−0.0029 (13)	−0.0043 (13)
C5	0.0170 (18)	0.0181 (17)	0.0207 (17)	−0.0027 (14)	−0.0072 (14)	−0.0086 (15)
C6	0.0155 (17)	0.0144 (17)	0.0177 (16)	0.0010 (14)	−0.0055 (13)	−0.0084 (14)
C7	0.0154 (17)	0.0165 (17)	0.0089 (15)	−0.0037 (14)	−0.0028 (13)	−0.0018 (13)
C8	0.0143 (17)	0.0193 (18)	0.0134 (16)	−0.0016 (14)	−0.0034 (14)	−0.0047 (14)
C13	0.0200 (19)	0.033 (2)	0.0253 (19)	0.0037 (17)	0.0043 (15)	−0.0167 (17)
C4	0.0171 (17)	0.0219 (18)	0.0232 (17)	−0.0021 (15)	−0.0010 (14)	−0.0137 (15)
C3	0.0126 (17)	0.0178 (18)	0.0129 (15)	−0.0037 (14)	−0.0026 (13)	−0.0058 (13)
C9	0.0150 (17)	0.029 (2)	0.0163 (17)	−0.0043 (15)	−0.0043 (14)	−0.0036 (15)
C10	0.026 (2)	0.030 (2)	0.0173 (17)	−0.0148 (16)	−0.0081 (15)	−0.0020 (16)
C11	0.0237 (19)	0.025 (2)	0.0201 (17)	−0.0062 (16)	−0.0086 (15)	−0.0092 (16)
C12	0.0187 (18)	0.025 (2)	0.0176 (17)	−0.0039 (15)	−0.0067 (14)	−0.0068 (15)

O1—N1	1.241 (3)	C7—C8	1.406 (4)
O3—C8	1.375 (4)	C8—C9	1.383 (5)
O3—C13	1.429 (4)	C13—H13C	0.96
O2—N1	1.236 (3)	C13—H13A	0.96
N1—C1	1.415 (4)	C13—H13B	0.96
N2—C2	1.317 (4)	C4—H4A	0.96
N2—C1	1.354 (4)	C4—H4B	0.96
N3—C3	1.339 (4)	C4—H4C	0.96
N3—C2	1.380 (4)	C3—H3	0.93
N3—C4	1.464 (4)	C9—C10	1.372 (5)
C1—C3	1.380 (4)	C9—H9	0.93
C2—C5	1.445 (5)	C10—C11	1.386 (5)
C5—C6	1.351 (5)	C10—H10	0.93
C5—H5	0.93	C11—C12	1.382 (5)
C6—C7	1.455 (5)	C11—H11	0.93
C6—H6	0.93	C12—H12	0.93
C7—C12	1.394 (5)
C8—O3—C13	117.1 (3)	O3—C13—H13A	109.5
O2—N1—O1	122.5 (3)	H13C—C13—H13A	109.5
O2—N1—C1	119.0 (3)	O3—C13—H13B	109.5
O1—N1—C1	118.4 (3)	H13C—C13—H13B	109.5
C2—N2—C1	103.9 (3)	H13A—C13—H13B	109.5
C3—N3—C2	108.4 (2)	N3—C4—H4A	109.5
C3—N3—C4	124.7 (3)	N3—C4—H4B	109.5
C2—N3—C4	126.7 (3)	H4A—C4—H4B	109.5
N2—C1—C3	112.9 (3)	N3—C4—H4C	109.5
N2—C1—N1	123.0 (3)	H4A—C4—H4C	109.5
C3—C1—N1	124.1 (3)	H4B—C4—H4C	109.5
N2—C2—N3	111.1 (3)	N3—C3—C1	103.7 (3)
N2—C2—C5	125.9 (3)	N3—C3—H3	128.1
N3—C2—C5	123.0 (3)	C1—C3—H3	128.1
C6—C5—C2	121.7 (3)	C10—C9—C8	120.0 (3)
C6—C5—H5	119.2	C10—C9—H9	120
C2—C5—H5	119.2	C8—C9—H9	120
C5—C6—C7	127.7 (3)	C9—C10—C11	120.6 (3)
C5—C6—H6	116.1	C9—C10—H10	119.7
C7—C6—H6	116.1	C11—C10—H10	119.7
C12—C7—C8	117.2 (3)	C12—C11—C10	119.2 (3)
C12—C7—C6	123.3 (3)	C12—C11—H11	120.4
C8—C7—C6	119.5 (3)	C10—C11—H11	120.4
O3—C8—C9	124.8 (3)	C11—C12—C7	121.9 (3)
O3—C8—C7	114.1 (3)	C11—C12—H12	119
C9—C8—C7	121.1 (3)	C7—C12—H12	119
O3—C13—H13C	109.5
C2—N2—C1—C3	0.3 (3)	C13—O3—C8—C9	−6.8 (5)
C2—N2—C1—N1	−178.3 (3)	C13—O3—C8—C7	173.6 (3)
O2—N1—C1—N2	−179.5 (3)	C12—C7—C8—O3	179.6 (3)
O1—N1—C1—N2	1.5 (4)	C6—C7—C8—O3	−0.6 (4)
O2—N1—C1—C3	2.0 (5)	C12—C7—C8—C9	−0.1 (5)
O1—N1—C1—C3	−176.9 (3)	C6—C7—C8—C9	179.8 (3)
C1—N2—C2—N3	0.1 (3)	C2—N3—C3—C1	0.6 (3)
C1—N2—C2—C5	−179.2 (3)	C4—N3—C3—C1	−175.4 (3)
C3—N3—C2—N2	−0.5 (3)	N2—C1—C3—N3	−0.5 (3)
C4—N3—C2—N2	175.4 (3)	N1—C1—C3—N3	178.1 (3)
C3—N3—C2—C5	178.9 (3)	O3—C8—C9—C10	−179.3 (3)
C4—N3—C2—C5	−5.3 (5)	C7—C8—C9—C10	0.3 (5)
N2—C2—C5—C6	−10.8 (5)	C8—C9—C10—C11	−0.7 (5)
N3—C2—C5—C6	170.0 (3)	C9—C10—C11—C12	0.8 (5)
C2—C5—C6—C7	178.6 (3)	C10—C11—C12—C7	−0.5 (5)
C5—C6—C7—C12	11.0 (5)	C8—C7—C12—C11	0.1 (5)
C5—C6—C7—C8	−168.8 (3)	C6—C7—C12—C11	−179.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.93	2.45	3.271 (4)	147
C4—H4B···O1ii	0.96	2.53	3.465 (5)	165
C6—H6···O3	0.93	2.31	2.685 (4)	103
C6—H6···N2	0.93	2.60	2.935 (4)	102

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.93	2.45	3.271 (4)	147
C4—H4B⋯O1ii	0.96	2.53	3.465 (5)	165
C6—H6⋯O3	0.93	2.31	2.685 (4)	103
C6—H6⋯N2	0.93	2.60	2.935 (4)	102

Symmetry codes: (i) ; (ii) .