N′-[(E)-1-Phenyl­ethyl­idene]benzo­hydrazide

Hoong-Kun Fun; K V Sujith; P S Patil; B Kalluraya; Suchada Chantrapromma

doi:10.1107/S1600536808029218

. 2008 Sep 20;64(Pt 10):o1961–o1962. doi: 10.1107/S1600536808029218

N′-[(E)-1-Phenylethylidene]benzohydrazide

Hoong-Kun Fun ^a,^*, K V Sujith ^b, P S Patil ^c,^‡, B Kalluraya ^b, Suchada Chantrapromma ^d,^§

PMCID: PMC2959329 PMID: 21201163

Abstract

The title compound, C₁₅H₁₄N₂O, crystallized with two independent molecules in the asymmetric unit. Both molecules are non-planar and have an E configuration with respect to the C=N bond. The dihedral angles between the two benzene rings are 11.1 (2)° in one molecule and 12.40 (19)° in the other. In the crystal structure, the molecules are linked by N—H⋯O hydrogen bonds and weak C—H⋯O interactions into infinite one-dimensional chains along [1 0 0]. The crystal structure is further stabilized by N—H⋯O hydrogen bonds, weak C—H⋯O and very weak C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to the applications of hydrazone and benzohydrazide, see, for example: Bratenko et al. (1999 ▶); Raj et al. (2007 ▶); Rollas et al. (2002 ▶); Sridhar et al. (2003 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

C₁₅H₁₄N₂O
M _r = 238.28
Orthorhombic,
a = 8.2237 (6) Å
b = 5.5938 (4) Å
c = 52.839 (4) Å
V = 2430.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100.0 (1) K
0.50 × 0.22 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.959, T _max = 0.996
23699 measured reflections
3572 independent reflections
2925 reflections with I > 2σ(I)
R _int = 0.069

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.159
S = 1.08
3572 reflections
327 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029218/si2108sup1.cif

e-64-o1961-sup1.cif^{(25.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029218/si2108Isup2.hkl

e-64-o1961-Isup2.hkl^{(175.2KB, 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
N2A—H2NA⋯O2Aⁱ	0.91	1.95	2.857 (4)	170
N2B—H2NB⋯O2Bⁱⁱ	0.73	2.17	2.866 (4)	161
C14A—H14A⋯O2Aⁱ	0.93	2.38	3.108 (5)	135
C14B—H14B⋯O2Bⁱⁱ	0.93	2.38	3.113 (5)	135
C15A—H15A⋯O2Aⁱ	0.96	2.58	3.053 (5)	110
C15B—H15D⋯O2Bⁱⁱ	0.96	2.44	3.038 (5)	120
C1A—H1AA⋯Cg1ⁱⁱ	0.93	2.96	3.729 (4)	141
C4A—H4AA⋯Cg1ⁱⁱⁱ	0.93	2.95	3.724 (5)	141
C1B—H1BA⋯Cg2ⁱ	0.93	2.88	3.726 (4)	141
C4B—H4BA⋯Cg2^iv	0.93	2.94	3.714 (4)	141

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 and Cg2 are the centroids of the C1A–C6A and C1B–C6B phenyl rings, respectively.

Acknowledgments

This work is supported by the Department of Science and Technology (DST), Government of India, under grant No. SR/S2/LOP-17/2006. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Hydrazones are versatile intermediates and important building blocks. Hydrazones of aliphatic and aromatic methyl ketones yield pyrazole-4-carboxaldehyde upon diformylation on treatment with Vilsmeier reagent (Bratenko et al., 1999). Aryl hydrazones are important building blocks for the synthesis of a variety of heterocyclic compounds such as pyrazolines and pyrazoles (Sridhar et al., 2003). Aryl hydrazones have been most conveniently synthesized by the reaction of aryl hydrazines with carbonyl compounds. Hydrazones have been demonstrated to possess antimicrobial, anticonvulsant, analgesic, antiinflammatory, antiplatelet, antitubercular, anticancer and antitumoral activities (Rollas et al., 2002). Hydrazones possessing an azometine -NHN=CH- proton constitute an important class of compounds for new drug development. Therefore, many researchers have synthesized these compounds as well as their metal complexes as target structures and evaluated their biological activities (Raj et al., 2007; Zhang et al., 2007). These observations guided us to synthesize the title compound and its crystal structure was reported here.

In the asymmetric unit of the title compound (Fig. 1), there are two independent molecules A and B. Bond lengths in molecules A and B are slightly different but all are in normal ranges (Allen et al., 1987). Both molecules are not planar and exist in the E configuration which respect to the C═N bond. The dihedral angles between the two benzene rings are 11.1 (2)° in A and 12.40 (19)° in B. In molecule A, the interplanar angle between the mean plane through N2A/O2A/C8A/C9A and N1A/N2A/C6A/C7A/C15A planes = 20.8 (2)°. In molecule B atoms N1B, N2B, C7B and C15B lie on the same plane and this plane makes the dihedral angle with the mean plane through N2B/O2B/C8B/C9B = 20.4 (2)°.

Fig. 2 shows that the molecules are linked into chains along [1 0 0] through N—H···O hydrogen bonds and weak C—H···O and very weak C—H···π interactions (Table 1); Cg₁, Cg₂, Cg₃ and Cg₄ are the centroids of the C1A–C6A, C1B–C6B, C9A–C14A and C9B–C14B rings, respectively.

Experimental

The title compound was obtained by refluxing phenyl hydrazide (0.01 mol) and acetophenone (0.01 mol) in ethanol (30 ml) by adding 3 drops of concentrated Sulfuric acid for 3 hr. Excess ethanol was removed from the reaction mixture under reduced pressure. The solid product obtained was filtered, washed with ethanol and dried. Colorless single crystals of the title compound suitable for x-ray structure determination were grown by slow evaporation of an ethanol solution at room temperature.