(E)-4-Amino-N'-(2-nitro-benzyl-idene)benzohydrazide.

The title Schiff base compound, C(14)H(12)N(4)O(3), displays an E conformation with respect to the C=N double bond [1.268 (3) Å]. The dihedral angle between the benzene rings is 3.2 (5)°, consistent with an essentially planar mol-ecule. In the crystal, N-H⋯O and N-H⋯N hydrogen bonds, as well as C-H⋯O inter-actions, link the mol-ecules into layers that stack along the c axis.

Related literature

For the coordination chemistry of Schiff base and n class="Chemical">hydrazone compounds, see: Kucukguzel et al. (2006 ▶); Khattab et al. (2005 ▶); Karthikeyan et al. (2006 ▶). For a closely related 4-amino­benzohydrazide and its Schiff base structures and further background references, see: Xu (2012 ▶); Shi & Li (2012 ▶); Bakir & Green (2002 ▶).

Experimental

Crystal data

C14H12N4O3

M = 284.28

Monoclinic,

a = 6.4594 (13) Å

b = 4.5998 (13) Å

c = 20.598 (5) Å

β = 95.08 (4)°

V = 609.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.11 mm−1

T = 296 K

0.25 × 0.18 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.976, T max = 0.989

4632 measured reflections

2710 independent reflections

1516 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.111

S = 1.05

2710 reflections

190 parameters

H-atom parameters constrained

Δρmax = 0.27 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/S1600536812020855/tk5092sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812020855/tk5092Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812020855/tk5092Isup3.cml

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

C14H12N4O3	F(000) = 296
Mr = 284.28	Dx = 1.549 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7138 reflections
a = 6.4594 (13) Å	θ = 1.4–27.5°
b = 4.5998 (13) Å	µ = 0.11 mm−1
c = 20.598 (5) Å	T = 296 K
β = 95.08 (4)°	Block, yellow
V = 609.6 (3) Å3	0.25 × 0.18 × 0.10 mm
Z = 2

Bruker SMART CCD area-detector diffractometer	2710 independent reflections
Radiation source: fine-focus sealed tube	1516 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→7
Tmin = 0.976, Tmax = 0.989	k = −6→5
4632 measured reflections	l = −26→24

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0576P)2 + 0.2479P] where P = (Fo2 + 2Fc2)/3
2710 reflections	(Δ/σ)max < 0.001
190 parameters	Δρmax = 0.27 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	0.6908 (3)	1.3470 (4)	0.16727 (9)	0.0252 (4)
O2	0.5696 (3)	0.5737 (5)	0.40854 (9)	0.0335 (5)
O3	0.3389 (3)	0.4666 (5)	0.47354 (9)	0.0338 (5)
N1	1.4552 (3)	0.7167 (6)	0.05402 (10)	0.0248 (5)
H1A	1.5039	0.8252	0.0236	0.030*
H1B	1.5583	0.6443	0.0811	0.030*
N2	0.6727 (3)	0.9187 (5)	0.21889 (9)	0.0193 (4)
H2	0.7097	0.7415	0.2215	0.023*
N3	0.5305 (3)	1.0250 (5)	0.25824 (9)	0.0198 (4)
N4	0.3968 (3)	0.6017 (5)	0.42806 (10)	0.0241 (5)
C1	1.2814 (3)	0.8062 (6)	0.08357 (11)	0.0196 (5)
C2	1.2309 (3)	0.6722 (6)	0.14030 (11)	0.0194 (5)
H2A	1.3134	0.5234	0.1585	0.023*
C3	1.0579 (3)	0.7606 (6)	0.16970 (11)	0.0190 (5)
H3	1.0271	0.6715	0.2078	0.023*
C4	0.9293 (3)	0.9809 (6)	0.14297 (11)	0.0188 (5)
C5	0.9786 (3)	1.1101 (6)	0.08586 (11)	0.0200 (5)
H5	0.8938	1.2555	0.0671	0.024*
C6	1.1522 (3)	1.0262 (6)	0.05623 (11)	0.0213 (5)
H6	1.1827	1.1162	0.0182	0.026*
C7	0.7535 (3)	1.0973 (6)	0.17592 (11)	0.0189 (5)
C8	0.4572 (3)	0.8400 (6)	0.29566 (11)	0.0196 (5)
H8	0.5066	0.6525	0.2978	0.024*
C9	0.2917 (3)	0.9327 (6)	0.33548 (11)	0.0188 (5)
C10	0.2529 (3)	0.8118 (6)	0.39485 (11)	0.0194 (5)
C11	0.0792 (4)	0.8859 (6)	0.42611 (11)	0.0230 (6)
H11	0.0555	0.7975	0.4650	0.028*
C12	−0.0568 (4)	1.0909 (7)	0.39888 (12)	0.0264 (6)
H12	−0.1735	1.1405	0.4191	0.032*
C13	−0.0189 (4)	1.2225 (6)	0.34132 (12)	0.0245 (5)
H13	−0.1085	1.3647	0.3236	0.029*
C14	0.1523 (3)	1.1439 (6)	0.30967 (12)	0.0218 (5)
H14	0.1746	1.2331	0.2707	0.026*

	U11	U22	U33	U12	U13	U23
O1	0.0270 (9)	0.0148 (9)	0.0353 (10)	0.0046 (7)	0.0107 (7)	0.0022 (8)
O2	0.0270 (8)	0.0396 (13)	0.0347 (10)	0.0120 (9)	0.0078 (7)	0.0073 (10)
O3	0.0390 (10)	0.0295 (12)	0.0336 (10)	0.0006 (9)	0.0069 (8)	0.0107 (10)
N1	0.0206 (9)	0.0285 (13)	0.0269 (10)	0.0033 (10)	0.0103 (7)	−0.0009 (11)
N2	0.0187 (9)	0.0158 (10)	0.0247 (9)	0.0043 (8)	0.0083 (7)	0.0010 (9)
N3	0.0182 (8)	0.0198 (11)	0.0223 (9)	0.0026 (8)	0.0061 (7)	−0.0025 (9)
N4	0.0269 (10)	0.0202 (11)	0.0256 (10)	0.0020 (9)	0.0052 (8)	−0.0012 (10)
C1	0.0170 (10)	0.0202 (13)	0.0222 (10)	−0.0017 (10)	0.0047 (8)	−0.0073 (11)
C2	0.0182 (10)	0.0164 (13)	0.0236 (11)	0.0029 (9)	0.0021 (8)	−0.0020 (10)
C3	0.0193 (10)	0.0154 (13)	0.0232 (11)	−0.0012 (9)	0.0060 (8)	−0.0008 (10)
C4	0.0164 (9)	0.0189 (13)	0.0215 (10)	0.0004 (10)	0.0034 (7)	−0.0039 (10)
C5	0.0204 (10)	0.0170 (12)	0.0227 (11)	0.0012 (10)	0.0024 (8)	0.0011 (11)
C6	0.0232 (11)	0.0208 (13)	0.0208 (10)	−0.0012 (10)	0.0068 (8)	−0.0008 (10)
C7	0.0181 (10)	0.0171 (12)	0.0222 (11)	−0.0012 (10)	0.0044 (8)	−0.0026 (11)
C8	0.0188 (9)	0.0181 (12)	0.0223 (10)	0.0010 (10)	0.0038 (8)	−0.0014 (11)
C9	0.0157 (9)	0.0153 (12)	0.0258 (11)	−0.0009 (9)	0.0045 (8)	−0.0028 (10)
C10	0.0188 (10)	0.0153 (12)	0.0243 (11)	0.0014 (10)	0.0028 (8)	−0.0007 (11)
C11	0.0251 (11)	0.0230 (15)	0.0223 (11)	−0.0018 (11)	0.0094 (8)	−0.0004 (11)
C12	0.0203 (10)	0.0318 (16)	0.0283 (12)	0.0023 (11)	0.0084 (9)	−0.0031 (13)
C13	0.0223 (10)	0.0216 (14)	0.0293 (12)	0.0035 (11)	0.0020 (9)	−0.0028 (12)
C14	0.0215 (10)	0.0187 (14)	0.0254 (11)	0.0013 (10)	0.0035 (8)	0.0010 (11)

O1—C7	1.226 (3)	C4—C5	1.380 (3)
O2—N4	1.226 (3)	C4—C7	1.474 (3)
O3—N4	1.211 (3)	C5—C6	1.378 (3)
N1—C1	1.386 (3)	C5—H5	0.9300
N1—H1A	0.8900	C6—H6	0.9300
N1—H1B	0.8900	C8—C9	1.467 (3)
N2—C7	1.346 (3)	C8—H8	0.9300
N2—N3	1.368 (3)	C9—C10	1.386 (3)
N2—H2	0.8600	C9—C14	1.397 (3)
N3—C8	1.268 (3)	C10—C11	1.385 (3)
N4—C10	1.470 (3)	C11—C12	1.378 (4)
C1—C2	1.385 (3)	C11—H11	0.9300
C1—C6	1.398 (3)	C12—C13	1.372 (4)
C2—C3	1.379 (3)	C12—H12	0.9300
C2—H2A	0.9300	C13—C14	1.381 (3)
C3—C4	1.393 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—H14	0.9300
C1—N1—H1A	120.0	C5—C6—H6	119.9
C1—N1—H1B	115.0	C1—C6—H6	119.9
H1A—N1—H1B	111.2	O1—C7—N2	121.8 (2)
C7—N2—N3	119.3 (2)	O1—C7—C4	122.1 (2)
C7—N2—H2	120.4	N2—C7—C4	116.1 (2)
N3—N2—H2	120.4	N3—C8—C9	118.3 (2)
C8—N3—N2	115.1 (2)	N3—C8—H8	120.9
O3—N4—O2	123.5 (2)	C9—C8—H8	120.9
O3—N4—C10	118.12 (19)	C10—C9—C14	117.0 (2)
O2—N4—C10	118.3 (2)	C10—C9—C8	125.2 (2)
C2—C1—N1	119.9 (2)	C14—C9—C8	117.8 (2)
C2—C1—C6	118.8 (2)	C9—C10—C11	121.9 (2)
N1—C1—C6	121.0 (2)	C9—C10—N4	121.26 (19)
C3—C2—C1	120.0 (2)	C11—C10—N4	116.7 (2)
C3—C2—H2A	119.9	C12—C11—C10	119.5 (2)
C1—C2—H2A	119.9	C12—C11—H11	120.2
C2—C3—C4	121.2 (2)	C10—C11—H11	120.2
C2—C3—H3	119.4	C11—C12—C13	119.7 (2)
C4—C3—H3	119.4	C11—C12—H12	120.2
C5—C4—C3	118.2 (2)	C13—C12—H12	120.2
C5—C4—C7	119.0 (2)	C12—C13—C14	120.6 (2)
C3—C4—C7	122.6 (2)	C12—C13—H13	119.7
C6—C5—C4	121.0 (2)	C14—C13—H13	119.7
C6—C5—H5	119.4	C13—C14—C9	121.2 (2)
C4—C5—H5	119.4	C13—C14—H14	119.4
C5—C6—C1	120.2 (2)	C9—C14—H14	119.4
C7—N2—N3—C8	177.7 (2)	N3—C8—C9—C10	−152.8 (2)
N1—C1—C2—C3	−179.9 (2)	N3—C8—C9—C14	32.2 (3)
C6—C1—C2—C3	−1.3 (4)	C14—C9—C10—C11	2.8 (4)
C1—C2—C3—C4	0.9 (4)	C8—C9—C10—C11	−172.1 (2)
C2—C3—C4—C5	0.1 (4)	C14—C9—C10—N4	−176.2 (2)
C2—C3—C4—C7	−174.8 (2)	C8—C9—C10—N4	8.9 (4)
C3—C4—C5—C6	−0.8 (4)	O3—N4—C10—C9	−167.6 (2)
C7—C4—C5—C6	174.3 (2)	O2—N4—C10—C9	12.8 (4)
C4—C5—C6—C1	0.3 (4)	O3—N4—C10—C11	13.3 (3)
C2—C1—C6—C5	0.7 (4)	O2—N4—C10—C11	−166.2 (2)
N1—C1—C6—C5	179.2 (2)	C9—C10—C11—C12	−1.9 (4)
N3—N2—C7—O1	−6.0 (3)	N4—C10—C11—C12	177.2 (2)
N3—N2—C7—C4	170.59 (19)	C10—C11—C12—C13	−0.5 (4)
C5—C4—C7—O1	−22.4 (4)	C11—C12—C13—C14	1.8 (4)
C3—C4—C7—O1	152.4 (2)	C12—C13—C14—C9	−0.7 (4)
C5—C4—C7—N2	161.0 (2)	C10—C9—C14—C13	−1.6 (4)
C3—C4—C7—N2	−24.1 (3)	C8—C9—C14—C13	173.8 (2)
N2—N3—C8—C9	−175.25 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N1i	0.89	2.44	3.287 (4)	162
N1—H1B···O1ii	0.89	2.35	3.164 (3)	153
N2—H2···O1iii	0.86	2.13	2.843 (3)	142
C2—H2A···O1ii	0.93	2.56	3.329 (3)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N1i	0.89	2.44	3.287 (4)	162
N1—H1B⋯O1ii	0.89	2.35	3.164 (3)	153
N2—H2⋯O1iii	0.86	2.13	2.843 (3)	142
C2—H2A⋯O1ii	0.93	2.56	3.329 (3)	140

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