(E)-4-Amino-N'-(3-nitro-benzyl-idene)benzohydrazide.

In the title compound, C(14)H(12)N(4)O(3), the dihedral angle between the benzene rings is 7.6 (4)°. In the crystal, infinite sheets linked by N-H⋯O and bifurcated N-H⋯(O,N) hydrogen bonds propagate in the (10-1) plane, in which R(4) (4)(36) loops are apparent. Neighbouring layers may inter-act by way of very weak π-π stacking inter-actions [centroid-centroid distances = 3.9329 (13) and 4.0702 (13) Å].

Related literature

For related structures and background references to hydrazones, see: Cao (2009 ▶); Zhou & Yang (2010 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C14H12N4O3

M = 284.28

Monoclinic,

a = 7.8909 (16) Å

b = 11.153 (2) Å

c = 14.709 (3) Å

β = 92.00 (3)°

V = 1293.7 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.20 × 0.15 × 0.12 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.981, T max = 0.987

11091 measured reflections

2952 independent reflections

2756 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.161

S = 1.06

2952 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.22 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812014110/hb6724sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812014110/hb6724Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812014110/hb6724Isup3.cml

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

C14H12N4O3	F(000) = 592
Mr = 284.28	Dx = 1.460 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3352 reflections
a = 7.8909 (16) Å	θ = 1.4–27.5°
b = 11.153 (2) Å	µ = 0.11 mm−1
c = 14.709 (3) Å	T = 296 K
β = 92.00 (3)°	Prism, yellow
V = 1293.7 (4) Å3	0.20 × 0.15 × 0.12 mm
Z = 4

Bruker SMART CCD diffractometer	2952 independent reflections
Radiation source: fine-focus sealed tube	2756 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.044
φ and ω scans	θmax = 27.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
Tmin = 0.981, Tmax = 0.987	k = −14→14
11091 measured reflections	l = −19→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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0851P)2 + 0.6295P] where P = (Fo2 + 2Fc2)/3
2952 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.13734 (17)	0.68729 (12)	0.42167 (9)	0.0318 (3)
O2	−0.0202 (2)	0.28779 (13)	0.14494 (10)	0.0405 (4)
O3	0.00112 (17)	0.09872 (13)	0.11390 (9)	0.0352 (4)
N1	0.3895 (2)	0.95096 (15)	0.79084 (11)	0.0333 (4)
H1B	0.3783	1.0286	0.7780	0.040*
H1A	0.4796	0.9306	0.8255	0.040*
N2	0.2130 (2)	0.52763 (13)	0.50999 (10)	0.0280 (4)
H2	0.2400	0.5032	0.5640	0.034*
N3	0.18734 (19)	0.44493 (14)	0.44124 (10)	0.0270 (3)
N4	0.02597 (19)	0.18540 (14)	0.16438 (10)	0.0286 (4)
C1	0.3493 (2)	0.87791 (17)	0.71707 (12)	0.0266 (4)
C2	0.2528 (2)	0.92102 (17)	0.64211 (12)	0.0294 (4)
H2A	0.2201	1.0011	0.6402	0.035*
C3	0.2060 (2)	0.84555 (16)	0.57111 (12)	0.0278 (4)
H3	0.1413	0.8756	0.5222	0.033*
C4	0.2540 (2)	0.72489 (16)	0.57130 (12)	0.0253 (4)
C5	0.3551 (2)	0.68367 (17)	0.64523 (12)	0.0286 (4)
H5	0.3921	0.6045	0.6459	0.034*
C6	0.4007 (2)	0.75809 (17)	0.71689 (12)	0.0289 (4)
H6	0.4663	0.7282	0.7655	0.035*
C7	0.1965 (2)	0.64721 (16)	0.49378 (12)	0.0259 (4)
C8	0.2188 (2)	0.33609 (17)	0.46441 (12)	0.0288 (4)
H8	0.2524	0.3187	0.5242	0.035*
C9	0.2025 (2)	0.23928 (16)	0.39805 (12)	0.0272 (4)
C10	0.1297 (2)	0.25889 (16)	0.31199 (12)	0.0262 (4)
H10	0.0924	0.3350	0.2949	0.031*
C11	0.1133 (2)	0.16422 (16)	0.25250 (12)	0.0259 (4)
C12	0.1707 (2)	0.04973 (17)	0.27327 (13)	0.0317 (4)
H12	0.1596	−0.0123	0.2312	0.038*
C13	0.2455 (3)	0.03068 (17)	0.35892 (14)	0.0345 (4)
H13	0.2862	−0.0450	0.3748	0.041*
C14	0.2596 (2)	0.12410 (18)	0.42087 (13)	0.0320 (4)
H14	0.3078	0.1100	0.4785	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0356 (7)	0.0343 (7)	0.0249 (7)	0.0026 (6)	−0.0065 (5)	0.0016 (5)
O2	0.0494 (9)	0.0321 (8)	0.0390 (8)	0.0013 (6)	−0.0126 (7)	0.0013 (6)
O3	0.0339 (7)	0.0356 (7)	0.0356 (7)	−0.0054 (6)	−0.0054 (6)	−0.0092 (6)
N1	0.0338 (9)	0.0346 (9)	0.0312 (8)	−0.0009 (7)	−0.0027 (7)	−0.0080 (7)
N2	0.0357 (8)	0.0278 (8)	0.0200 (7)	−0.0016 (6)	−0.0046 (6)	−0.0012 (6)
N3	0.0278 (8)	0.0290 (8)	0.0240 (7)	−0.0020 (6)	−0.0015 (6)	−0.0035 (6)
N4	0.0267 (8)	0.0298 (8)	0.0294 (8)	−0.0023 (6)	−0.0011 (6)	−0.0009 (6)
C1	0.0210 (8)	0.0326 (9)	0.0262 (9)	−0.0028 (7)	0.0021 (6)	−0.0045 (7)
C2	0.0314 (9)	0.0256 (8)	0.0312 (9)	−0.0025 (7)	0.0011 (7)	−0.0001 (7)
C3	0.0277 (9)	0.0288 (9)	0.0267 (9)	−0.0001 (7)	−0.0016 (7)	0.0021 (7)
C4	0.0237 (8)	0.0290 (9)	0.0233 (8)	−0.0012 (7)	0.0008 (6)	−0.0008 (7)
C5	0.0282 (9)	0.0270 (9)	0.0302 (9)	0.0004 (7)	−0.0031 (7)	−0.0019 (7)
C6	0.0263 (9)	0.0344 (10)	0.0255 (9)	0.0006 (7)	−0.0057 (7)	−0.0009 (7)
C7	0.0233 (8)	0.0302 (9)	0.0239 (8)	0.0002 (7)	−0.0008 (6)	0.0000 (7)
C8	0.0283 (9)	0.0320 (9)	0.0256 (9)	0.0004 (7)	−0.0043 (7)	−0.0011 (7)
C9	0.0248 (8)	0.0292 (9)	0.0274 (9)	−0.0001 (7)	−0.0011 (7)	−0.0008 (7)
C10	0.0233 (8)	0.0258 (8)	0.0294 (9)	−0.0009 (7)	0.0002 (7)	−0.0005 (7)
C11	0.0240 (8)	0.0282 (9)	0.0254 (9)	−0.0017 (7)	0.0001 (7)	−0.0002 (7)
C12	0.0343 (10)	0.0271 (9)	0.0337 (10)	0.0014 (8)	0.0025 (8)	−0.0030 (7)
C13	0.0377 (10)	0.0282 (9)	0.0376 (10)	0.0084 (8)	0.0013 (8)	0.0012 (8)
C14	0.0323 (10)	0.0344 (10)	0.0292 (9)	0.0046 (8)	−0.0017 (7)	0.0030 (7)

O1—C7	1.228 (2)	C4—C5	1.403 (3)
O2—N4	1.229 (2)	C4—C7	1.490 (2)
O3—N4	1.231 (2)	C5—C6	1.380 (2)
N1—C1	1.385 (2)	C5—H5	0.9300
N1—H1B	0.8899	C6—H6	0.9300
N1—H1A	0.8900	C8—C9	1.458 (2)
N2—C7	1.360 (2)	C8—H8	0.9300
N2—N3	1.378 (2)	C9—C10	1.389 (3)
N2—H2	0.8600	C9—C14	1.398 (3)
N3—C8	1.283 (2)	C10—C11	1.375 (2)
N4—C11	1.466 (2)	C10—H10	0.9300
C1—C6	1.397 (3)	C11—C12	1.385 (3)
C1—C2	1.403 (3)	C12—C13	1.389 (3)
C2—C3	1.382 (3)	C12—H12	0.9300
C2—H2A	0.9300	C13—C14	1.386 (3)
C3—C4	1.398 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C1—N1—H1B	112.8	C5—C6—H6	119.7
C1—N1—H1A	117.1	C1—C6—H6	119.7
H1B—N1—H1A	116.1	O1—C7—N2	122.65 (17)
C7—N2—N3	121.12 (15)	O1—C7—C4	123.07 (17)
C7—N2—H2	119.4	N2—C7—C4	114.27 (15)
N3—N2—H2	119.4	N3—C8—C9	120.75 (17)
C8—N3—N2	114.60 (15)	N3—C8—H8	119.6
O2—N4—O3	123.35 (16)	C9—C8—H8	119.6
O2—N4—C11	118.80 (15)	C10—C9—C14	118.88 (17)
O3—N4—C11	117.84 (15)	C10—C9—C8	121.15 (17)
N1—C1—C6	120.38 (17)	C14—C9—C8	119.97 (16)
N1—C1—C2	121.16 (17)	C11—C10—C9	119.06 (17)
C6—C1—C2	118.44 (17)	C11—C10—H10	120.5
C3—C2—C1	120.58 (17)	C9—C10—H10	120.5
C3—C2—H2A	119.7	C10—C11—C12	123.03 (17)
C1—C2—H2A	119.7	C10—C11—N4	118.02 (16)
C2—C3—C4	121.31 (17)	C12—C11—N4	118.92 (16)
C2—C3—H3	119.3	C11—C12—C13	117.80 (17)
C4—C3—H3	119.3	C11—C12—H12	121.1
C3—C4—C5	117.62 (16)	C13—C12—H12	121.1
C3—C4—C7	118.86 (16)	C14—C13—C12	120.21 (18)
C5—C4—C7	123.52 (17)	C14—C13—H13	119.9
C6—C5—C4	121.40 (17)	C12—C13—H13	119.9
C6—C5—H5	119.3	C13—C14—C9	120.99 (18)
C4—C5—H5	119.3	C13—C14—H14	119.5
C5—C6—C1	120.60 (17)	C9—C14—H14	119.5
C7—N2—N3—C8	175.27 (16)	N2—N3—C8—C9	−178.03 (15)
N1—C1—C2—C3	−176.57 (17)	N3—C8—C9—C10	−9.4 (3)
C6—C1—C2—C3	1.8 (3)	N3—C8—C9—C14	171.08 (18)
C1—C2—C3—C4	−0.5 (3)	C14—C9—C10—C11	1.1 (3)
C2—C3—C4—C5	−1.5 (3)	C8—C9—C10—C11	−178.44 (16)
C2—C3—C4—C7	178.64 (16)	C9—C10—C11—C12	−1.9 (3)
C3—C4—C5—C6	2.3 (3)	C9—C10—C11—N4	176.03 (15)
C7—C4—C5—C6	−177.89 (17)	O2—N4—C11—C10	4.2 (2)
C4—C5—C6—C1	−1.0 (3)	O3—N4—C11—C10	−175.03 (16)
N1—C1—C6—C5	177.33 (17)	O2—N4—C11—C12	−177.78 (17)
C2—C1—C6—C5	−1.1 (3)	O3—N4—C11—C12	3.0 (2)
N3—N2—C7—O1	9.7 (3)	C10—C11—C12—C13	1.0 (3)
N3—N2—C7—C4	−171.05 (15)	N4—C11—C12—C13	−176.84 (16)
C3—C4—C7—O1	14.6 (3)	C11—C12—C13—C14	0.6 (3)
C5—C4—C7—O1	−165.29 (17)	C12—C13—C14—C9	−1.3 (3)
C3—C4—C7—N2	−164.70 (16)	C10—C9—C14—C13	0.5 (3)
C5—C4—C7—N2	15.5 (3)	C8—C9—C14—C13	180.00 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1i	0.86	2.47	3.183 (2)	141
N2—H2···O3ii	0.86	2.44	3.041 (2)	127
N1—H1A···O1iii	0.89	2.27	3.106 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1i	0.86	2.47	3.183 (2)	141
N2—H2⋯O3ii	0.86	2.44	3.041 (2)	127
N1—H1A⋯O1iii	0.89	2.27	3.106 (2)	156

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