(E)-4-Amino-N′-(3-nitro­benzyl­idene)benzohydrazide

Shu-Qing Xu

doi:10.1107/S1600536812014110

. 2012 Apr 6;68(Pt 5):o1320. doi: 10.1107/S1600536812014110

(E)-4-Amino-N′-(3-nitrobenzylidene)benzohydrazide

Shu-Qing Xu ^a,^*

PMCID: PMC3344459 PMID: 22590221

Abstract

In the title compound, C₁₄H₁₂N₄O₃, 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 interact by way of very weak π–π stacking interactions [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 _r = 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
Δρ_max = 0.22 e Å⁻³
Δρ_min = −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.

Supplementary Material

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

e-68-o1320-sup1.cif^{(17KB, cif)}

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

e-68-o1320-Isup2.hkl^{(144.9KB, hkl)}

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

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

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

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

Acknowledgments

This work was supported by the Natural Science Foundation of Guangxi Province (grant No. 2011GXNSFA018123). The author also acknowledges financial support from the Natural Science Foundation of Education Bureau of Guangxi Province (grant No. 201106LX537).

supplementary crystallographic information

Comment

As an extension of recent studies of hydrazone Schiff bases, (Cao, 2009; Zhou & Yang, 2010), the title compound was prepared and characterized.

As shown in Fig. 1, the asymmetric unit of the title compound, (I), contains one independent molecule displaying an E configuration with respect to its C═N double bond. The dihedral angle between the two benzene rings is 7.6 (4) °. The bond lengths and angles are as expected for a compound of this type and agree with the other ligands belonging to the hydrazone series. The C8═N3 and C7═O1 bond lengths of 1.283 (2) and 1.228 (2) Å, respectively, conform to the values for double bonds. Whereas the C1-N1, C8-N3, C11-N4 and N2-N3 [1.385 (2), 1.360 (2), 1.466 (2) and 1.378 (2) Å, respectively] bond lengths correspond to a single bond. In the crystal packing, it is noted that one of amino H (H1A) and amide H2 are involved in forming intermolecular N—H···O and N—H···N hydrogen bonds, which link the molecules into a R⁴₄(36) graph-set notation (Fig. 2 and Table 1). These rings form an alternating sequence, in turn, linking the molecules into a two-dimensional supramolecular sheet structure parallel to (101). Neighboring layers are further interacting with each other through weak π–π stacking interactions [centroid to centroid distances of the benzene C1/C6 and C9/C14 rings are 3.93 (6) and 4.07 (6) Å].

Experimental

3-Nitrobenzaldehyde (1 mmol, 0.151 g) and 4-aminobenzohydrazide (1 mmol, 0.151 g) were dissolved in MeOH (20 ml). The mixture was stirred for 6 hours at room temperature to give a yellow solution. Yellow prisms were formed by gradual evaporation of the solvent over a period of 5 days at room temperature.