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

In the title mol-ecule, C13H13N3O2, the planes of the benzene and imidazole rings form a dihedral angle of 7.72 (5)°. In the crystal, mol-ecules are linked by weak C-H⋯N and C-H⋯O hydrogen bonds, forming layers parallel to (100). A weak C-H⋯π inter-action connects these layers into a three-dimensional network. A π-π stacking inter-action, with a centroid-centroid distance of 3.5373 (9) Å, is also observed.

Related literature

For the synthesis and applications of imidazole derivatives, see: Mamedov et al. (2011 ▶); De Luca (2006 ▶); Teimouri & Chermahini (2011 ▶); Achar et al. (2010 ▶); Özkay et al. (2010 ▶); Shingalapur et al. (2009 ▶); Bhatia & Shanbhag (1984 ▶); Hoffer & Grunberg (1974 ▶). For the biological activity of nitro­imidazole derivatives, see: Trivedi et al. (2011 ▶); Leitsch et al. (2011 ▶); Luo et al. (2010 ▶); Saadeh et al. (2009 ▶); Thompson et al. (2009 ▶); Carvalho et al. (2006 ▶); Alliouche et al. (2014 ▶); Hunkeler et al. (1981 ▶); Tanigawara et al. (1999 ▶).

Experimental

Crystal data

C13H13N3O2

M = 243.26

Monoclinic,

a = 7.1774 (8) Å

b = 15.7931 (16) Å

c = 10.7901 (11) Å

β = 101.798 (6)°

V = 1197.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 150 K

0.16 × 0.06 × 0.05 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T min = 0.891, T max = 1.000

9856 measured reflections

2113 independent reflections

1958 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.094

S = 1.05

2113 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.31 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/S1600536814017243/lh5721sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017243/lh5721Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814017243/lh5721Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814017243/lh5721fig1.tif

The mol­ecular structure structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

c . DOI: 10.1107/S1600536814017243/lh5721fig2.tif

The crystal packing of (I) viewed along the c axis showing weak C—H⋯O hydrogen bonds as dashed lines.

Click here for additional data file.

a . DOI: 10.1107/S1600536814017243/lh5721fig3.tif

The crystal packing of (I) viewed along the a axis showing weak C—H⋯O and C—H⋯N hydrogen bonds as dashed lines.

CCDC reference: 1016150

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

C13H13N3O2	F(000) = 512
Mr = 243.26	Dx = 1.35 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6402 reflections
a = 7.1774 (8) Å	θ = 2.3–25.1°
b = 15.7931 (16) Å	µ = 0.09 mm−1
c = 10.7901 (11) Å	T = 150 K
β = 101.798 (6)°	Needle, colorless
V = 1197.3 (2) Å3	0.16 × 0.06 × 0.05 mm
Z = 4

Bruker APEXII diffractometer	1958 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
CCD rotation images, thin slices scans	θmax = 25.1°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −8→8
Tmin = 0.891, Tmax = 1.000	k = −18→18
9856 measured reflections	l = −12→12
2113 independent 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.712P] where P = (Fo2 + 2Fc2)/3
2113 reflections	(Δ/σ)max = 0.005
165 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.31 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
N2	0.41984 (15)	0.20989 (7)	0.58571 (10)	0.0142 (3)
O1B	0.58852 (16)	0.36479 (6)	0.59448 (9)	0.0234 (3)
O1A	0.62422 (14)	0.36871 (6)	0.79969 (9)	0.0214 (3)
N3	0.37372 (15)	0.13617 (7)	0.75347 (10)	0.0136 (3)
N1	0.56745 (16)	0.33418 (7)	0.69608 (10)	0.0154 (3)
C12	0.16578 (19)	−0.08459 (9)	0.37141 (12)	0.0173 (3)
H12	0.1714	−0.0947	0.457	0.021*
C1	0.47447 (18)	0.25439 (8)	0.69479 (12)	0.0138 (3)
C7	0.20697 (18)	−0.00361 (8)	0.33138 (12)	0.0148 (3)
C3	0.35902 (18)	0.13706 (8)	0.62364 (12)	0.0136 (3)
C9	0.15285 (19)	−0.05791 (9)	0.11606 (13)	0.0177 (3)
H9	0.1512	−0.0485	0.0308	0.021*
C5	0.29083 (19)	0.06490 (8)	0.54450 (12)	0.0157 (3)
H5	0.265	0.0148	0.5831	0.019*
C2	0.44778 (18)	0.21119 (8)	0.79988 (12)	0.0141 (3)
H2	0.4744	0.2293	0.8837	0.017*
C11	0.11685 (19)	−0.14954 (9)	0.28511 (13)	0.0187 (3)
H11	0.0879	−0.2025	0.3138	0.022*
C6	0.26340 (18)	0.06724 (8)	0.41831 (12)	0.0157 (3)
H6	0.2821	0.1192	0.3821	0.019*
C10	0.10965 (19)	−0.13770 (9)	0.15583 (13)	0.0182 (3)
C4	0.3300 (2)	0.06497 (8)	0.82950 (12)	0.0169 (3)
H4A	0.4249	0.0217	0.8324	0.025*
H4B	0.2073	0.0424	0.7921	0.025*
H4C	0.3293	0.0841	0.9139	0.025*
C13	0.0545 (2)	−0.20885 (10)	0.06267 (14)	0.0255 (3)
H13A	−0.0782	−0.2215	0.055	0.038*
H13B	0.1287	−0.2582	0.092	0.038*
H13C	0.0779	−0.1923	−0.0184	0.038*
C8	0.19843 (19)	0.00802 (9)	0.20157 (12)	0.0168 (3)
H8	0.224	0.0613	0.1722	0.02*

	U11	U22	U33	U12	U13	U23
N2	0.0171 (6)	0.0135 (6)	0.0119 (5)	0.0024 (4)	0.0024 (4)	−0.0006 (4)
O1B	0.0390 (6)	0.0180 (5)	0.0150 (5)	−0.0046 (4)	0.0093 (4)	0.0023 (4)
O1A	0.0312 (6)	0.0174 (5)	0.0144 (5)	−0.0033 (4)	0.0019 (4)	−0.0040 (4)
N3	0.0162 (6)	0.0129 (6)	0.0118 (5)	0.0014 (4)	0.0033 (4)	0.0011 (4)
N1	0.0199 (6)	0.0129 (6)	0.0136 (6)	0.0026 (4)	0.0037 (4)	−0.0001 (4)
C12	0.0190 (7)	0.0184 (7)	0.0135 (6)	0.0014 (5)	0.0016 (5)	0.0007 (5)
C1	0.0164 (6)	0.0116 (6)	0.0135 (6)	0.0027 (5)	0.0034 (5)	−0.0002 (5)
C7	0.0122 (6)	0.0175 (7)	0.0147 (6)	0.0012 (5)	0.0024 (5)	−0.0013 (5)
C3	0.0137 (6)	0.0148 (7)	0.0123 (6)	0.0031 (5)	0.0028 (5)	0.0012 (5)
C9	0.0153 (7)	0.0249 (7)	0.0130 (6)	0.0016 (5)	0.0030 (5)	−0.0021 (5)
C5	0.0172 (7)	0.0139 (6)	0.0163 (7)	0.0003 (5)	0.0040 (5)	−0.0001 (5)
C2	0.0164 (6)	0.0134 (6)	0.0126 (6)	0.0028 (5)	0.0028 (5)	−0.0015 (5)
C11	0.0182 (7)	0.0150 (7)	0.0216 (7)	0.0007 (5)	0.0014 (5)	0.0013 (5)
C6	0.0158 (7)	0.0142 (7)	0.0176 (7)	0.0002 (5)	0.0043 (5)	0.0010 (5)
C10	0.0126 (6)	0.0207 (7)	0.0202 (7)	0.0029 (5)	0.0008 (5)	−0.0055 (6)
C4	0.0211 (7)	0.0165 (7)	0.0136 (6)	−0.0008 (5)	0.0049 (5)	0.0029 (5)
C13	0.0260 (8)	0.0249 (8)	0.0238 (8)	−0.0004 (6)	0.0009 (6)	−0.0088 (6)
C8	0.0157 (7)	0.0181 (7)	0.0170 (7)	−0.0003 (5)	0.0043 (5)	0.0011 (5)

N2—C3	1.3244 (17)	C9—C10	1.387 (2)
N2—C1	1.3581 (17)	C9—H9	0.93
O1B—N1	1.2354 (15)	C5—C6	1.3358 (19)
O1A—N1	1.2357 (15)	C5—H5	0.93
N3—C2	1.3522 (17)	C2—H2	0.93
N3—C3	1.3832 (16)	C11—C10	1.398 (2)
N3—C4	1.4631 (16)	C11—H11	0.93
N1—C1	1.4246 (17)	C6—H6	0.93
C12—C11	1.3816 (19)	C10—C13	1.5057 (19)
C12—C7	1.4006 (19)	C4—H4A	0.96
C12—H12	0.93	C4—H4B	0.96
C1—C2	1.3700 (18)	C4—H4C	0.96
C7—C8	1.4015 (19)	C13—H13A	0.96
C7—C6	1.4632 (18)	C13—H13B	0.96
C3—C5	1.4479 (18)	C13—H13C	0.96
C9—C8	1.3853 (19)	C8—H8	0.93
C3—N2—C1	103.69 (11)	N3—C2—H2	128
C2—N3—C3	108.00 (11)	C1—C2—H2	128
C2—N3—C4	125.37 (11)	C12—C11—C10	121.71 (13)
C3—N3—C4	126.51 (11)	C12—C11—H11	119.1
O1B—N1—O1A	123.54 (11)	C10—C11—H11	119.1
O1B—N1—C1	118.65 (11)	C5—C6—C7	126.59 (13)
O1A—N1—C1	117.80 (11)	C5—C6—H6	116.7
C11—C12—C7	120.71 (12)	C7—C6—H6	116.7
C11—C12—H12	119.6	C9—C10—C11	117.74 (12)
C7—C12—H12	119.6	C9—C10—C13	121.09 (13)
N2—C1—C2	113.28 (12)	C11—C10—C13	121.16 (13)
N2—C1—N1	121.19 (11)	N3—C4—H4A	109.5
C2—C1—N1	125.23 (12)	N3—C4—H4B	109.5
C12—C7—C8	117.33 (12)	H4A—C4—H4B	109.5
C12—C7—C6	123.28 (12)	N3—C4—H4C	109.5
C8—C7—C6	119.36 (12)	H4A—C4—H4C	109.5
N2—C3—N3	111.11 (11)	H4B—C4—H4C	109.5
N2—C3—C5	126.46 (12)	C10—C13—H13A	109.5
N3—C3—C5	122.40 (11)	C10—C13—H13B	109.5
C8—C9—C10	120.94 (12)	H13A—C13—H13B	109.5
C8—C9—H9	119.5	C10—C13—H13C	109.5
C10—C9—H9	119.5	H13A—C13—H13C	109.5
C6—C5—C3	122.75 (12)	H13B—C13—H13C	109.5
C6—C5—H5	118.6	C9—C8—C7	121.55 (13)
C3—C5—H5	118.6	C9—C8—H8	119.2
N3—C2—C1	103.93 (11)	C7—C8—H8	119.2
C3—N2—C1—C2	−0.46 (15)	C3—N3—C2—C1	0.06 (14)
C3—N2—C1—N1	173.57 (11)	C4—N3—C2—C1	176.18 (12)
O1B—N1—C1—N2	3.97 (18)	N2—C1—C2—N3	0.25 (15)
O1A—N1—C1—N2	−175.44 (11)	N1—C1—C2—N3	−173.49 (12)
O1B—N1—C1—C2	177.24 (12)	C7—C12—C11—C10	1.1 (2)
O1A—N1—C1—C2	−2.16 (19)	C3—C5—C6—C7	175.78 (12)
C11—C12—C7—C8	−0.70 (19)	C12—C7—C6—C5	2.8 (2)
C11—C12—C7—C6	−178.70 (12)	C8—C7—C6—C5	−175.12 (13)
C1—N2—C3—N3	0.48 (14)	C8—C9—C10—C11	−1.05 (19)
C1—N2—C3—C5	−177.57 (12)	C8—C9—C10—C13	178.22 (12)
C2—N3—C3—N2	−0.35 (14)	C12—C11—C10—C9	−0.2 (2)
C4—N3—C3—N2	−176.42 (11)	C12—C11—C10—C13	−179.50 (13)
C2—N3—C3—C5	177.79 (12)	C10—C9—C8—C7	1.5 (2)
C4—N3—C3—C5	1.73 (19)	C12—C7—C8—C9	−0.57 (19)
N2—C3—C5—C6	−7.0 (2)	C6—C7—C8—C9	177.51 (12)
N3—C3—C5—C6	175.11 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2i	0.93	2.49	3.3702 (17)	159
C4—H4C···O1Bi	0.96	2.54	3.2676 (17)	133
C13—H13B···O1Aii	0.96	2.59	3.5347 (19)	168
C4—H4B···Cgiii	0.96	2.61	3.4336 (16)	144

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N2i	0.93	2.49	3.3702 (17)	159
C4—H4C⋯O1B i	0.96	2.54	3.2676 (17)	133
C13—H13B⋯O1A ii	0.96	2.59	3.5347 (19)	168
C4—H4B⋯Cg iii	0.96	2.61	3.4336 (16)	144

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