(E)-N'-(4-Meth-oxy-benzyl-idene)-2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetohydrazide.

In the title compound, C(14)H(15)N(5)O(4), the central -C=N-N-C(=O)-C- bridge is nearly planar [maximum deviation = 0.037 (1) Å] and forms dihedral angles of 7.37 (9) and 73.33 (5)°, respectively, with the benzene and imidazole rings. The dihedral angle between the benzene and imidazole rings is 66.08 (9)°. The meth-oxy and nitro groups are nearly coplanar with the benzene and imidazole rings, respectively, with a C-O-C-C torsion angle of 5.9 (2)° and an O-N-C-C angle of -0.2 (2)°. In the crystal, mol-ecules are linked by a pair of N-H⋯O hydrogen bonds with an R(2) (2)(8) ring motif, forming an inversion dimer. The dimers are further inter-connected by C-H⋯O hydrogen bonds into a sheet parallel to the (111) plane. A C-H⋯π inter-action is also observed between the sheets.

Related literature

For applications and biological activities of imidazole derivatives, see: Frank & Kalluraya (2005 ▶); Dobler (2003 ▶); Gauthier & Duceppe (1984 ▶); Khan & n class="Chemical">Nandan (1997 ▶); Khabnadideh et al. (2003 ▶). For the stability of the temperature controller used for data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H15N5O4

M = 317.31

Triclinic,

a = 4.3366 (1) Å

b = 12.9773 (3) Å

c = 13.2138 (3) Å

α = 84.919 (2)°

β = 87.353 (2)°

γ = 84.611 (1)°

V = 736.90 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.51 × 0.19 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.947, T max = 0.988

15663 measured reflections

4303 independent reflections

3252 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.131

S = 1.03

4303 reflections

214 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAIn class="Chemical">NT; 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 datablock(s) global, I. DOI: 10.1107/S1600536812039621/is5195sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039621/is5195Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812039621/is5195Isup3.cml

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

C14H15N5O4	Z = 2
Mr = 317.31	F(000) = 332
Triclinic, P1	Dx = 1.430 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.3366 (1) Å	Cell parameters from 5229 reflections
b = 12.9773 (3) Å	θ = 2.3–30.0°
c = 13.2138 (3) Å	µ = 0.11 mm−1
α = 84.919 (2)°	T = 100 K
β = 87.353 (2)°	Plate, yellow
γ = 84.611 (1)°	0.51 × 0.19 × 0.11 mm
V = 736.90 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4303 independent reflections
Radiation source: fine-focus sealed tube	3252 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.035
φ and ω scans	θmax = 30.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.947, Tmax = 0.988	k = −18→18
15663 measured reflections	l = −18→18

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0518P)2 + 0.496P] where P = (Fo2 + 2Fc2)/3
4303 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.34 e Å−3
0 restraints	Δρmin = −0.31 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 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	−0.4105 (3)	0.76565 (9)	1.00477 (9)	0.0228 (3)
O2	1.0816 (3)	0.88398 (8)	0.42690 (8)	0.0168 (2)
O3	1.4713 (3)	0.47331 (9)	0.20227 (9)	0.0237 (3)
O4	1.5848 (3)	0.44149 (9)	0.36131 (9)	0.0256 (3)
N1	0.5223 (3)	0.85992 (9)	0.62488 (10)	0.0157 (3)
N2	0.7370 (3)	0.90552 (10)	0.55866 (10)	0.0151 (3)
N3	0.9336 (3)	0.68443 (9)	0.40406 (10)	0.0156 (3)
N4	1.0435 (3)	0.63333 (9)	0.24863 (10)	0.0164 (3)
N5	1.4374 (3)	0.49076 (9)	0.29156 (10)	0.0175 (3)
C1	−0.4567 (4)	0.65710 (13)	1.02022 (13)	0.0243 (4)
H1A	−0.6064	0.6458	1.0771	0.036*
H1B	−0.2590	0.6171	1.0357	0.036*
H1C	−0.5361	0.6344	0.9584	0.036*
C2	−0.2144 (4)	0.79626 (12)	0.92693 (12)	0.0178 (3)
C3	−0.0763 (4)	0.73140 (12)	0.85563 (12)	0.0181 (3)
H3A	−0.1178	0.6605	0.8593	0.022*
C4	0.1213 (4)	0.77065 (11)	0.77954 (12)	0.0164 (3)
H4A	0.2139	0.7261	0.7311	0.020*
C5	0.1872 (4)	0.87453 (11)	0.77251 (11)	0.0149 (3)
C6	0.0467 (4)	0.93826 (12)	0.84475 (12)	0.0193 (3)
H6A	0.0893	1.0090	0.8415	0.023*
C7	−0.1527 (4)	0.90054 (12)	0.92063 (12)	0.0204 (3)
H7A	−0.2477	0.9453	0.9685	0.025*
C8	0.4071 (4)	0.91518 (11)	0.69559 (12)	0.0155 (3)
H8A	0.4658	0.9836	0.6979	0.019*
C9	0.8830 (4)	0.84969 (11)	0.48733 (11)	0.0141 (3)
C10	0.7805 (4)	0.74033 (11)	0.48597 (12)	0.0172 (3)
H10A	0.8265	0.7006	0.5518	0.021*
H10B	0.5534	0.7452	0.4782	0.021*
C11	1.1547 (4)	0.60235 (11)	0.41596 (12)	0.0162 (3)
H11A	1.2447	0.5722	0.4771	0.019*
C12	1.2159 (4)	0.57381 (11)	0.31963 (12)	0.0156 (3)
C13	0.8741 (4)	0.70062 (11)	0.30221 (12)	0.0156 (3)
C14	0.6539 (4)	0.78659 (12)	0.26004 (13)	0.0197 (3)
H14A	0.6200	0.7773	0.1887	0.030*
H14B	0.7403	0.8531	0.2645	0.030*
H14C	0.4563	0.7861	0.2991	0.030*
H1N2	0.792 (5)	0.9681 (18)	0.5660 (16)	0.031 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0275 (7)	0.0223 (6)	0.0192 (6)	−0.0081 (5)	0.0062 (5)	−0.0019 (4)
O2	0.0186 (6)	0.0126 (5)	0.0197 (5)	−0.0047 (4)	0.0036 (4)	−0.0028 (4)
O3	0.0346 (7)	0.0162 (5)	0.0199 (6)	0.0018 (5)	0.0016 (5)	−0.0055 (4)
O4	0.0341 (7)	0.0176 (5)	0.0242 (6)	0.0067 (5)	−0.0071 (5)	−0.0021 (5)
N1	0.0165 (6)	0.0127 (5)	0.0178 (6)	−0.0019 (5)	0.0009 (5)	−0.0012 (5)
N2	0.0173 (7)	0.0104 (5)	0.0181 (6)	−0.0040 (5)	0.0031 (5)	−0.0033 (5)
N3	0.0200 (7)	0.0099 (5)	0.0174 (6)	−0.0032 (5)	0.0016 (5)	−0.0034 (4)
N4	0.0195 (7)	0.0113 (5)	0.0185 (6)	−0.0022 (5)	0.0003 (5)	−0.0023 (5)
N5	0.0228 (7)	0.0096 (5)	0.0204 (7)	−0.0017 (5)	−0.0009 (5)	−0.0025 (5)
C1	0.0275 (9)	0.0232 (8)	0.0224 (8)	−0.0092 (7)	0.0021 (7)	0.0024 (6)
C2	0.0183 (8)	0.0197 (7)	0.0155 (7)	−0.0027 (6)	0.0003 (6)	−0.0007 (6)
C3	0.0219 (8)	0.0135 (6)	0.0191 (7)	−0.0031 (6)	−0.0011 (6)	−0.0009 (5)
C4	0.0175 (8)	0.0140 (6)	0.0179 (7)	0.0000 (6)	0.0002 (6)	−0.0034 (5)
C5	0.0151 (7)	0.0128 (6)	0.0168 (7)	−0.0007 (6)	−0.0005 (6)	−0.0020 (5)
C6	0.0232 (8)	0.0131 (6)	0.0221 (8)	−0.0024 (6)	0.0008 (7)	−0.0045 (6)
C7	0.0231 (8)	0.0182 (7)	0.0204 (8)	−0.0022 (6)	0.0040 (7)	−0.0065 (6)
C8	0.0173 (7)	0.0112 (6)	0.0182 (7)	−0.0009 (6)	−0.0017 (6)	−0.0021 (5)
C9	0.0153 (7)	0.0111 (6)	0.0163 (7)	−0.0014 (5)	−0.0019 (6)	−0.0022 (5)
C10	0.0223 (8)	0.0128 (6)	0.0173 (7)	−0.0046 (6)	0.0050 (6)	−0.0047 (5)
C11	0.0205 (8)	0.0101 (6)	0.0185 (7)	−0.0034 (6)	−0.0003 (6)	−0.0015 (5)
C12	0.0178 (8)	0.0102 (6)	0.0190 (7)	−0.0023 (6)	0.0009 (6)	−0.0017 (5)
C13	0.0188 (8)	0.0096 (6)	0.0191 (7)	−0.0035 (6)	0.0002 (6)	−0.0029 (5)
C14	0.0229 (8)	0.0130 (6)	0.0229 (8)	0.0016 (6)	−0.0023 (7)	−0.0025 (6)

O1—C2	1.3599 (19)	C3—C4	1.384 (2)
O1—C1	1.437 (2)	C3—H3A	0.9500
O2—C9	1.2340 (18)	C4—C5	1.398 (2)
O3—N5	1.2206 (17)	C4—H4A	0.9500
O4—N5	1.2410 (18)	C5—C6	1.399 (2)
N1—C8	1.2825 (19)	C5—C8	1.460 (2)
N1—N2	1.3853 (17)	C6—C7	1.380 (2)
N2—C9	1.3394 (19)	C6—H6A	0.9500
N2—H1N2	0.88 (2)	C7—H7A	0.9500
N3—C11	1.368 (2)	C8—H8A	0.9500
N3—C13	1.376 (2)	C9—C10	1.5284 (19)
N3—C10	1.4565 (19)	C10—H10A	0.9900
N4—C13	1.3208 (19)	C10—H10B	0.9900
N4—C12	1.365 (2)	C11—C12	1.364 (2)
N5—C12	1.4371 (19)	C11—H11A	0.9500
C1—H1A	0.9800	C13—C14	1.485 (2)
C1—H1B	0.9800	C14—H14A	0.9800
C1—H1C	0.9800	C14—H14B	0.9800
C2—C3	1.396 (2)	C14—H14C	0.9800
C2—C7	1.399 (2)
C2—O1—C1	117.64 (13)	C5—C6—H6A	119.3
C8—N1—N2	115.67 (12)	C6—C7—C2	119.82 (14)
C9—N2—N1	118.95 (12)	C6—C7—H7A	120.1
C9—N2—H1N2	119.3 (14)	C2—C7—H7A	120.1
N1—N2—H1N2	121.5 (14)	N1—C8—C5	121.01 (13)
C11—N3—C13	107.62 (12)	N1—C8—H8A	119.5
C11—N3—C10	125.49 (13)	C5—C8—H8A	119.5
C13—N3—C10	126.83 (13)	O2—C9—N2	122.86 (13)
C13—N4—C12	103.74 (13)	O2—C9—C10	122.67 (13)
O3—N5—O4	124.20 (14)	N2—C9—C10	114.47 (13)
O3—N5—C12	119.08 (13)	N3—C10—C9	112.56 (12)
O4—N5—C12	116.72 (13)	N3—C10—H10A	109.1
O1—C1—H1A	109.5	C9—C10—H10A	109.1
O1—C1—H1B	109.5	N3—C10—H10B	109.1
H1A—C1—H1B	109.5	C9—C10—H10B	109.1
O1—C1—H1C	109.5	H10A—C10—H10B	107.8
H1A—C1—H1C	109.5	C12—C11—N3	103.93 (14)
H1B—C1—H1C	109.5	C12—C11—H11A	128.0
O1—C2—C3	124.58 (14)	N3—C11—H11A	128.0
O1—C2—C7	115.76 (14)	C11—C12—N4	113.11 (14)
C3—C2—C7	119.66 (14)	C11—C12—N5	125.50 (14)
C4—C3—C2	119.79 (14)	N4—C12—N5	121.40 (13)
C4—C3—H3A	120.1	N4—C13—N3	111.59 (14)
C2—C3—H3A	120.1	N4—C13—C14	125.55 (14)
C3—C4—C5	121.31 (14)	N3—C13—C14	122.82 (13)
C3—C4—H4A	119.3	C13—C14—H14A	109.5
C5—C4—H4A	119.3	C13—C14—H14B	109.5
C4—C5—C6	118.03 (14)	H14A—C14—H14B	109.5
C4—C5—C8	121.61 (13)	C13—C14—H14C	109.5
C6—C5—C8	120.30 (13)	H14A—C14—H14C	109.5
C7—C6—C5	121.39 (14)	H14B—C14—H14C	109.5
C7—C6—H6A	119.3
C8—N1—N2—C9	175.35 (14)	C13—N3—C10—C9	−74.30 (19)
C1—O1—C2—C3	5.9 (2)	O2—C9—C10—N3	−2.2 (2)
C1—O1—C2—C7	−174.01 (15)	N2—C9—C10—N3	177.07 (14)
O1—C2—C3—C4	−179.73 (15)	C13—N3—C11—C12	0.07 (16)
C7—C2—C3—C4	0.2 (3)	C10—N3—C11—C12	177.30 (13)
C2—C3—C4—C5	0.2 (2)	N3—C11—C12—N4	−0.37 (17)
C3—C4—C5—C6	−0.2 (2)	N3—C11—C12—N5	179.33 (13)
C3—C4—C5—C8	176.91 (15)	C13—N4—C12—C11	0.52 (17)
C4—C5—C6—C7	−0.3 (2)	C13—N4—C12—N5	−179.19 (13)
C8—C5—C6—C7	−177.45 (16)	O3—N5—C12—C11	−179.70 (15)
C5—C6—C7—C2	0.8 (3)	O4—N5—C12—C11	−0.2 (2)
O1—C2—C7—C6	179.25 (16)	O3—N5—C12—N4	0.0 (2)
C3—C2—C7—C6	−0.7 (3)	O4—N5—C12—N4	179.49 (14)
N2—N1—C8—C5	−177.68 (14)	C12—N4—C13—N3	−0.46 (16)
C4—C5—C8—N1	7.6 (2)	C12—N4—C13—C14	177.23 (15)
C6—C5—C8—N1	−175.37 (15)	C11—N3—C13—N4	0.26 (17)
N1—N2—C9—O2	−178.50 (14)	C10—N3—C13—N4	−176.93 (13)
N1—N2—C9—C10	2.3 (2)	C11—N3—C13—C14	−177.51 (14)
C11—N3—C10—C9	108.99 (16)	C10—N3—C13—C14	5.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2i	0.88 (2)	2.06 (2)	2.9372 (17)	176 (2)
C11—H11A···O4ii	0.95	2.28	3.186 (2)	160
C14—H14A···O1iii	0.98	2.46	3.434 (2)	173
C14—H14C···Cg1iv	0.98	2.74	3.4747 (18)	133

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N3/C11/C12/N4/C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2i	0.88 (2)	2.06 (2)	2.9372 (17)	176 (2)
C11—H11A⋯O4ii	0.95	2.28	3.186 (2)	160
C14—H14A⋯O1iii	0.98	2.46	3.434 (2)	173
C14—H14C⋯Cg1iv	0.98	2.74	3.4747 (18)	133

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