N′-(3-Bromo-5-chloro-2-hydroxy­benzyl­idene)-2-methoxy­benzohydrazide

Jin-Long Hou

doi:10.1107/S1600536809010198

. 2009 Mar 25;65(Pt 4):o851. doi: 10.1107/S1600536809010198

N′-(3-Bromo-5-chloro-2-hydroxybenzylidene)-2-methoxybenzohydrazide

Jin-Long Hou ^a,^*

PMCID: PMC2969039 PMID: 21582569

Abstract

The title compound, C₁₅H₁₂BrClN₂O₃, was obtained by the condensation reaction between 3-bromo-5-chloro-2-hydroxybenzaldehyde and 2-methoxybenzohydrazide. The molecule is essentially planar, with a dihedral angle between the two benzene rings of 4.7 (2)°, and displays an E configuration about the C=N double bond. The molecular conformation is stabilized by intramolecular O—H⋯N and N—H⋯O hydrogen bonds. In the crystal structure, molecules are linked into zigzag chains running parallel to the c axis by intermolecular C—H⋯O hydrogen bonds. The chains are further connected through aromatic π–π stacking interactions with centroid–centroid distances of 3.583 (4) Å.

Related literature

For the biological properties of hydrazone compounds, see: Cukurovali et al. (2006 ▶); Karthikeyan et al. (2006 ▶); Kucukguzel et al. (2006 ▶). For the crystal structures of related hydrazone compounds, see: Mohd Lair et al. (2009 ▶); Fun et al. (2008 ▶); Zhang et al. (2009 ▶); Khaledi et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₂BrClN₂O₃
M _r = 383.63
Monoclinic,
a = 10.883 (1) Å
b = 12.863 (2) Å
c = 10.950 (1) Å
β = 96.027 (3)°
V = 1524.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 2.89 mm⁻¹
T = 298 K
0.12 × 0.12 × 0.10 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.709, T _max = 0.746
4397 measured reflections
2323 independent reflections
1906 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.062
S = 1.02
2323 reflections
205 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ▶), 671 Friedel pairs
Flack parameter: 0.068 (12)

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 datablocks global, I. DOI: 10.1107/S1600536809010198/rz2301sup1.cif

e-65-0o851-sup1.cif^{(16.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010198/rz2301Isup2.hkl

e-65-0o851-Isup2.hkl^{(114.2KB, 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
O1—H1⋯N1	0.82	1.83	2.549 (4)	146
N2—H2⋯O3	0.895 (10)	1.92 (3)	2.623 (4)	134 (4)
C6—H6⋯O2ⁱ	0.93	2.45	3.315 (6)	154

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financially support from Qiqihar University is gratefully acknowledged.

supplementary crystallographic information

Comment

Hydrazones derived from the condensation reactions of hydrazides with aldehydes show excellent biological properties (Cukurovali et al., 2006; Karthikeyan et al., 2006; Kucukguzel et al., 2006). In the last two years, several hydrazone compounds have been structurally characterized (Mohd Lair et al., 2009; Fun et al., 2008; Zhang et al., 2009; Khaledi et al., 2008). In this paper, the synthesis and crystal structure of the title compound, derived from the condensation reaction of 3-bromo-5-chloro-2-hydroxybenzaldehyde and 2-methoxybenzohydrazide, is reported.

The molecular structure of the title compound is shown in Fig. 1. The molecule is essentially planar (mean deviation 0.010 (4) Å) and displays an E configuration about the C═N double bond. All bond lengths are within normal ranges (Allen et al., 1987). The molecular conformation is stabilized by intramolecular O—H···N and N—H···O hydrogen bonds (Table 1). In the crystal structure, the molecules are linked into zig-zag chains running parallel to the c axis by intermolecular C—H···O hydrogen bonds. The chains are further connected by aromatic π-π stacking interactions: Cp1···Cp2ⁱ = 3.583 (4) Å, perpendicular interplanar distance = 3.430 (4) Å, Cp1···Cp2ⁱ offset = 1.037 (3) Å [Cp1 and Cp2 are the centroids of the C9–C14 and C1–C6 armatic rings, respectively. Symmetry code: (i) -1/2+x, -1/2+y, z].

Experimental

3-Bromo-5-chloro-2-hydroxybenzaldehyde (1.0 mmol, 235.5 mg) and 2-methoxybenzohydrazide (1.0 mmol, 166.2 mg) were mixed and refluxed with stirring for two hours. Yellow single crystals were formed after slow evaporation of the solution in air for a week.