N′-(2,4-Dinitro­phen­yl)benzohydrazide

Aamer Saeed; Ifzan Arshad; Ulrich Flörke

doi:10.1107/S1600536812030619

. 2012 Jul 10;68(Pt 8):o2418. doi: 10.1107/S1600536812030619

N′-(2,4-Dinitrophenyl)benzohydrazide

Aamer Saeed ^a,^*, Ifzan Arshad ^a, Ulrich Flörke ^b

PMCID: PMC3414336 PMID: 22904869

Abstract

In the title compound, C₁₃H₁₀N₄O₅, the aromatic ring planes are close to perpendicular [dihedral angle = 75.94 (5)°] and the C—N—N—C torsion angle is 88.7 (2)°. Both nitro groups lie close to their attached ring plane, with C—C—N—O torsion angles of 3.1 (2) and 5.3 (2)°. This allows for the formation of an intramolecular N—H⋯O hydrogen bond, which closes an S(6) ring. In the crystal, N—H⋯O hydrogen bonds link the molecules into zigzag chains extending along [100].

Related literature

For a related structure, see: Wardell et al. (2007 ▶).

Experimental

Crystal data

C₁₃H₁₀N₄O₅
M _r = 302.25
Monoclinic,
a = 13.5714 (10) Å
b = 8.4621 (6) Å
c = 11.4547 (9) Å
β = 93.830 (2)°
V = 1312.55 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 130 K
0.48 × 0.20 × 0.19 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.944, T _max = 0.977
6295 measured reflections
1673 independent reflections
1599 reflections with I > 2σ(I)
R _int = 0.018

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.083
S = 1.06
1673 reflections
206 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812030619/hb6871sup1.cif

e-68-o2418-sup1.cif^{(17.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030619/hb6871Isup2.hkl

e-68-o2418-Isup2.hkl^{(82.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812030619/hb6871Isup3.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
N1—H1⋯O1ⁱ	0.92 (3)	1.96 (3)	2.803 (2)	151 (2)
N2—H2⋯O3ⁱⁱ	0.81 (3)	2.30 (2)	2.968 (2)	140 (2)
N2—H2⋯O3	0.81 (3)	2.02 (2)	2.606 (2)	129 (2)

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

Acknowledgments

AS gratefully acknowledges a research grant from the Higher Education Commission of Pakistan under the project No. 4-279/PAK-US/HEC 2010-917 (Pakistan–US Science and Technology Cooperation Program).

supplementary crystallographic information

Comment

The PhC(O)NNPh core moiety of the title compound (Figure 1) is similar to that of N-anilino-4-nitrobenzamide (Wardell et al., 2007) with different ring substituents. The molecular conformation is determined by an intra-molecular N2–H···O3 hydrogen bond with H···O3 2.02 (2) Å and an associated torsion angle N2–C8–C9–N3 of -0.1 (3)°. The inter-molecular hydrogen bonds N1–H···O1(-x+0.5, y+0.5, -z) with H···O 1.96 (3) Å and N-H···O 151 (2)° as well as N2–H···O3(-x, y, -z) with H···O 2.30 (2) Å and C-H···O 140 (2)° link molecules into zigzag chains extended along the a-axis (Figure 2).

Experimental

2,4-Dinitrophenyl hydrazine (2.8 mmol) in dry CH₂Cl₂ was treated with benzoyl chloride (2.8 mmol) and the mixture was refluxed for 3 hours. On completion of reaction, the mixture was allowed to cool and excess of solvent was evaporated under reduced pressure. Yellow prisms of the title compound were recrystallized from ethanol solution by slow evaporation of the solvent at room temperature (m.p 213-215°C).