N′-(3-Bromo-5-chloro-2-hy­droxy­benzyl­idene)-2H-1,3-benzodioxole-5-carbo­hydrazide

Jiao Wei; Hong-Yan Ban; Xiao-Zhi Sun

doi:10.1107/S160053681201433X

. 2012 Apr 6;68(Pt 5):o1336–o1337. doi: 10.1107/S160053681201433X

N′-(3-Bromo-5-chloro-2-hydroxybenzylidene)-2H-1,3-benzodioxole-5-carbohydrazide

Jiao Wei ^a, Hong-Yan Ban ^a,^*, Xiao-Zhi Sun ^a

PMCID: PMC3344473 PMID: 22590235

Abstract

The asymmetric unit of the title hydrazone compound, C₁₅H₁₀BrClN₂O₄, contains two independent molecules. The dihedral angles between the benzene rings are 38.7 (3)° in one molecule and 24.3 (3)° in the other. Both molecules exist in trans conformations with respect to the C=N double bonds of the central methylidene units. Intramolecular O—H⋯N contacts are observed in both molecules, forming S(6) rings. In the crystal, molecules are linked through N—H⋯O hydrogen bonds into chains along the a axis.

Related literature

For the biological activity of hydrazones, see: Zhong et al. (2007 ▶); Raj et al. (2007 ▶); Jimenez-Pulido et al. (2008 ▶). For related structures, see: Ban (2010 ▶); Ban & Li (2008a ▶,b ▶); Li & Ban (2009a ▶,b ▶); Yehye et al. (2008 ▶); Fun et al. (2008a ▶,b ▶); Yang et al. (2008 ▶); Ejsmont et al. (2008 ▶); Yang (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₀BrClN₂O₄
M _r = 397.61
Triclinic,
a = 9.769 (2) Å
b = 13.041 (3) Å
c = 13.251 (3) Å
α = 75.558 (2)°
β = 78.745 (2)°
γ = 76.527 (2)°
V = 1572.9 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.80 mm⁻¹
T = 298 K
0.12 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.730, T _max = 0.767
8062 measured reflections
5662 independent reflections
3817 reflections with I > 2σ(I)
R _int = 0.019

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.137
S = 1.01
5662 reflections
423 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.23 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201433X/sj5231sup1.cif

e-68-o1336-sup1.cif^{(29.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201433X/sj5231Isup2.hkl

e-68-o1336-Isup2.hkl^{(277.2KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201433X/sj5231Isup3.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
N2—H2⋯O4ⁱ	0.90 (1)	2.00 (2)	2.872 (4)	162 (5)
O3—H3⋯N3	0.82	1.92	2.637 (4)	145
O1—H1⋯N1	0.82	1.85	2.561 (4)	145

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the 7th issue of the Undergraduate’s Research and Training Project of the University of Science and Technology Liaoning, and the Youth Foundation of the University of Science and Technology Liaoning (2010Y06).

supplementary crystallographic information

Comment

Hydrazone compounds derived from the condensation of aldehydes with hydrazides have been demonstrated to possess excellent biological activities (Zhong et al., 2007; Raj et al., 2007; Jimenez-Pulido et al., 2008). Due to the easy synthesis of such compounds, a number of hydrazone compounds have been synthesized and structurally characterized (Yehye et al., 2008; Fun et al., 2008a,b; Yang et al., 2008; Ejsmont et al., 2008; Yang, 2006). Recently, we have reported several such compounds (Ban, 2010; Ban & Li, 2008a,b; Li & Ban, 2009a,b). We report here the crystal structure of the new title benzohydrazide derivative.

The asymmetric unit of the title hydrazone compound, Fig. 1, contains two independent molecules. The dihedral angles between the two benzene rings are 38.7 (3) and 24.3 (3)°, respectively. The molecules exist in trans configuration with respect to the central methylidene units. Intramolecular O1—H1···N1 and O3—H3···N3 contacts are observed forming S(6) rings (Bernstein et al., 1995). In the crystal structure, molecules are linked through intermolecular N—H···O hydrogen bonds (Table 1), forming chains along the a axis, Fig. 2.

Experimental

The title compound was prepared by refluxing 3-bromo-5-chlorosalicylaldehyde (1.0 mol, 0.23 g) with [3,4]dioxolebenzohydrazide (1.0 mol, 0.18 g) in methanol (50 ml). Excess methanol was removed from the mixture by distillation. A colourless solid product was filtered, and washed three times with methanol. Colourless block-shaped crystals of the title compound were obtained from a methanol solution of the compound by slow evaporation in air.