(E)-N′-[1-(Thio­phen-2-yl)ethyl­idene]benzohydrazide

Shang Shan; Yan-Lan Huang; Han-Qi Guo; Deng-Feng Li; Jian Sun

doi:10.1107/S1600536811033101

. 2011 Aug 27;67(Pt 9):o2498. doi: 10.1107/S1600536811033101

(E)-N′-[1-(Thiophen-2-yl)ethylidene]benzohydrazide

Shang Shan ^a,^*, Yan-Lan Huang ^a, Han-Qi Guo ^a, Deng-Feng Li ^a, Jian Sun ^a

PMCID: PMC3200815 PMID: 22059048

Abstract

The title compound, C₁₃H₁₂N₂OS, was obtained from the condensation reaction of 2-acetylthiophene and benzohydrazide. In the molecule, the formohydrazide fragment is approximately planar (r.m.s deviation = 0.0146 Å) and the mean plane is oriented at dihedral angles of 24.47 (11) and 28.86 (13)°, respectively, to the phenyl and thiophene rings. The thiophene and phenyl rings make a dihedral angle of 53.21 (8)°. The benzamide fragment and thiophene ring are located on the opposite sides of the C=N bond, showing an E conformation. Classical intermolecular N—H⋯O hydrogen bonds and weak C—H⋯O interactions are present in the crystal structure: three such bonds occur to the same O-atom acceptor.

Related literature

For applications of hydrazone derivatives in the biological field, see: Okabe et al. (1993 ▶). For general background to this work, see: Qiang et al. (2007 ▶). For a related structures, see: Xia et al. (2009 ▶); Shan et al. (2011 ▶)

Experimental

Crystal data

C₁₃H₁₂N₂OS
M _r = 244.31
Orthorhombic,
a = 9.906 (3) Å
b = 10.542 (5) Å
c = 22.870 (5) Å
V = 2388.3 (14) Å³
Z = 8
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 294 K
0.32 × 0.29 × 0.28 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
7859 measured reflections
2153 independent reflections
1552 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.101
S = 1.03
2153 reflections
155 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033101/xu6116sup1.cif

e-67-o2498-sup1.cif^{(15.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033101/xu6116Isup2.hkl

e-67-o2498-Isup2.hkl^{(103.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033101/xu6116Isup3.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	0.86	2.50	3.340 (3)	166
C2—H2⋯O1ⁱ	0.93	2.43	3.251 (3)	147
C13—H13A⋯O1ⁱ	0.96	2.40	3.246 (3)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

The work was supported by the Natural Science Foundation of Zhejiang Province, China (No. M203027).

supplementary crystallographic information

Comment

The hydrazone derivatives has attracted our much attention because they have shown to be potential DNA damaging and mutagenic agents (Okabe et al., 1993). As part of the ongoing investigation on the relationship between structure and property of hydrazone derivatives (Qiang et al., 2007) the title compound has recently been prepared in our laboratory and its crystal structure is reported here.

The molecular structure of the title compound is shown in Fig. 1. In the molecule, the formohydrazide fragment is approximately co-planar [r.m.s deviation = 0.0146 Å] and the mean plane is oriented with respect to the phenyl ring and thiophene ring at 24.47 (11) and 28.86 (13)°, respectively. The N2—C8 bond length of 1.286 (2) Å shows a typical C═N double bond. The thiophene and benzamide units are located on the opposite sites of the C═N bond, showing an E configuration.

Intermolecular N—H···O and weak C—H···O hydrogen bonding is present in the crystal structure (Table 1).

Experimental

Benzohydrazide (0.68 g, 5 mmol) was dissolved in ethanol (25 ml), then acetic acid (0.2 ml) was added to the ethanol solution with stirring. The solution was heated at about 333 K for several minutes until it became clear. 2-Acetylthiophene (0.63 g, 5 mmol) was then added slowly into the solution, and the mixture solution was refluxed for 6 h. After cooling to room temperature, yellow microcrystals appeared. The microcrystals were separated from the solution and washed with cold water three times. Recrystallization was performed twice with absolute methanol to obtain single crystals of the title compound.