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

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.

The title compound, C 15 H 12 BrClN 2 O 3 , 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-HÁ Á ÁN and N-HÁ Á ÁO hydrogen bonds. In the crystal structure, molecules are linked into zigzag chains running parallel to the c axis by intermolecular C-HÁ Á ÁO hydrogen bonds. The chains are further connected through aromaticstacking interactions with centroid-centroid distances of 3.583 (4) Å .

Experimental
Financially support from Qiqihar University is gratefully acknowledged.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2301).
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···Cp2 i = 3.583 (4) Å, perpendicular interplanar distance = 3.430 (4) Å, Cp1···Cp2 i 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]. 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.

Refinement
H2 was located in a difference Fourier map and refined isotropically, with the N-H distance restrained to 0.90 (1) Å, and with the U iso (H) value fixed at 0.08 Å 2 . All other H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C-H = 0.93-0.96 Å, O-H = 0.82 Å, and with U iso (H) set at 1.2U eq (C) or 1.5U eq (O).