N′-(2,6-Dichloro­benzyl­idene)furan-2-carbohydrazide

Jun Xu

doi:10.1107/S160053681201639X

. 2012 Apr 21;68(Pt 5):o1455. doi: 10.1107/S160053681201639X

N′-(2,6-Dichlorobenzylidene)furan-2-carbohydrazide

Jun Xu ^a,^*

PMCID: PMC3344570 PMID: 22590332

Abstract

In the title compound, C₁₂H₈Cl₂N₂O₂, the dihedral angle between the furan and benzene rings is 72.90 (16)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds, generating C(4) chains propagating in [100].

Related literature

For related structures, see: Okabe et al. (1993 ▶); Ohba (1996 ▶); Bakir & Gyles (2003 ▶).

Experimental

Crystal data

C₁₂H₈Cl₂N₂O₂
M _r = 283.10
Monoclinic,
a = 4.9046 (3) Å
b = 19.1113 (12) Å
c = 12.9469 (9) Å
β = 91.565 (5)°
V = 1213.10 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.53 mm⁻¹
T = 293 K
0.21 × 0.18 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.814, T _max = 0.847
4654 measured reflections
2464 independent reflections
1679 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.126
S = 1.01
2464 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); 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/S160053681201639X/hb6741sup1.cif

e-68-o1455-sup1.cif^{(14.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201639X/hb6741Isup2.hkl

e-68-o1455-Isup2.hkl^{(121.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201639X/hb6741Isup3.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—H1A⋯O1ⁱ	0.86	2.07	2.890 (2)	159

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Several phenylhydrazone derivatives have been shown to be potentially DNA-damaging and are mutagenic agents (Okabe et al., 1993). As part of our ongoing studies of these materials, we synthesized the title compound, (I), and the crystal structure is presented herein. In the molecular structure of the compound, the molecular is not planar, the furyl ring makes a dihedral angle of 72.90 (16)° with the benzene ring. Bond lengths and angles are in agreement with other hydrazone derivatives (Ohba, 1996; Bakir & Gyles, 2003).

In the crystal, molecules are linked by N—H···O hydrogen bonds, generating one-dimensional chains.

Experimental

Furan-2-carbohydrazine (1 mmol, 0.126 g) was dissolved in anhydrous ethanol (10 ml), The mixture was stirred for several minitutes at 351k, 2,6-Dichlorobenzaldehyde (1 mmol, 0.175 g) in ethanol (20 mm l) was added dropwise and the mixture was stirred at refluxing temperature for 2 h. The product was isolated and recrystallized from DMF. Colorless blocks were obtained by slow evaporation of the compound dissoived in a mixture of ethanol and DMF.