N′-[1-(2-Amino­phen­yl)ethyl­idene]benzo­hydrazide

Vinod P Singh; Shweta Singh

doi:10.1107/S1600536810010937

. 2010 Apr 24;66(Pt 5):o1172. doi: 10.1107/S1600536810010937

N′-[1-(2-Aminophenyl)ethylidene]benzohydrazide

Vinod P Singh ^a,^*, Shweta Singh ^a

PMCID: PMC2979270 PMID: 21579213

Abstract

The title compound, C₁₅H₁₅N₃O, was obtained by a condensation reaction between o-aminoacetophenone and benzoyl hydrazine. The molecule displays an E configuration about the C=N bond. Intramolecular N—H⋯N hydrogen bonds are formed between the 2-aminophenyl and imine groups. In the crystal, dimers are formed between molecules linked by intermolecular N—H⋯O hydrogen bonds from the 2-aminophenyl group. In addition there are intermolecular N—H⋯O hydrogen bonds between the amine and carbonyl groups of adjacent molecules. The molecule is twisted rather than planar due to a steric interaction between the central amide group and the two outer benzene rings. The dihedral angles between this central group and the two rings are 23.29 (9) and 24.96 (9)°.

Related literature

For the biological properties of hydrazones derived from the condensation reactions of hydrazides with aldehydes or ketones, see: Gupta et al. (2007 ▶); Kocyigit-Kaymakcioglu et al. (2009 ▶); Kou et al. (2009 ▶); Mahalingam et al. (2009 ▶); Sundaraval et al. (2009 ▶); Yin et al. (2007 ▶); Zhang et al. (2007 ▶). For related structures, see: Fun et al. (2008a ▶,b ▶); Qiu & Zhao (2008 ▶); Qiu (2009 ▶); Ren (2009 ▶); Xiao & Wei (2009 ▶).

Experimental

Crystal data

C₁₅H₁₅N₃O
M _r = 253.30
Monoclinic,
a = 13.7531 (10) Å
b = 5.1575 (3) Å
c = 18.7178 (13) Å
β = 105.917 (7)°
V = 1276.78 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.33 × 0.25 × 0.13 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.780, T _max = 1.000
5257 measured reflections
2894 independent reflections
1839 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.125
S = 0.98
2894 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1999 ▶); software used to prepare material for publication: CIFTAB (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010937/bv2135sup1.cif

e-66-o1172-sup1.cif^{(17.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010937/bv2135Isup2.hkl

e-66-o1172-Isup2.hkl^{(139.2KB, hkl)}

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
N3—H3B⋯O1ⁱ	0.86	2.41	3.1611 (15)	147
N1—H1A⋯O1ⁱⁱ	0.86	2.29	3.0856 (16)	154
N1—H1B⋯N2	0.86	2.03	2.6626 (16)	130

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

Acknowledgments

The authors thank the CSIR for financial support.

supplementary crystallographic information

Comment

Hydrazones derived from the condensation reactions of hydrazides with aldehydes or ketones show excellent biological properties, such as antimicrobial, antitubercular, anticancer and antimalarial (Kocyigit-Kaymakcioglu et al., 2009; Kou et al., 2009; Mahalingam et al.., 2009; Sundaravel et al., 2009; Yin et al., 2007; Zhang et al.,2007. The hydrazones are also important for their use as plasticizers and stabilizers for polymers, polymerization initiators, antioxidants and as indicators (Gupta et al., 2007). Recently, a large number of hydrazone compounds have been reported (Qiu et al., 2008; Qiu, 2009; Ren et al., 2009). In this paper, a new hydrazone compound, derived from the condensation reaction of 2-aminoacetophenone and benzoyl hydrazine, has been reported.

The molecular structure of the title compound is shown in the fig. 1. The molecule and displays an E configuration about the C=N double bond. All bond lengths are within normal ranges (Xiao et al., 2009; Fun et al., 2008a,b). The molecular conformation is stabilized by an intramolecular N—H···.O hydrogen bond and short contact bonds (Fig. 1). In the crystal there are both inter- and intra-molecular hydrogen bonding involving the amine protons. In-plane dimers (r.m.s. deviation for N1 N2 N3 C10–C16 and equivalent atoms = 0.016 Å) are formed between molecules linked by N—H···O hydrogen bonds from the 2-aminophenyl moiety (Fig. 2). In addition there are intermolecular out of plane N—H···O hydrogen bonds between amine and carbonyl group of adjoining molecules (Fig. 3). Intramolecular N—H···N hydrogen bonds are formed between the 2-aminophenyl and imine moieties within the same molecule. The molecule is twisted rather than planar due to steric interaction between the central amide group and the two end groups. The torsion angles between this central group and the two ends are 23.29 (9) and 24.96 (9)° respectively.

Experimental

An ethanolic solution of benzoyl hydazine (50 ml, 6.8 g) was taken in a round bottom flask followed by dropwise addition of ethanolic solution of o-aminoacetophenone (50 ml, 6.05 ml) with stirring. The above solution was refluxed for 4-5 h and gave a yellow transparent solution. On keeping the solution in open air for 5-6 h in a beaker, yellow crystals of the product were obtained.