N′-(5-Bromo-2-hydr­oxy-3-methoxy­benzyl­idene)-4-hydr­oxy-3-methoxy­benzohydrazide dihydrate

Jiu-Fu Lu; Suo-Tian Min; Hong-Guang Ge; Xiao-Hui Ji; Yue-Fei Bai

doi:10.1107/S1600536809033522

. 2009 Aug 29;65(Pt 9):o2259. doi: 10.1107/S1600536809033522

N′-(5-Bromo-2-hydroxy-3-methoxybenzylidene)-4-hydroxy-3-methoxybenzohydrazide dihydrate

Jiu-Fu Lu ^a,^*, Suo-Tian Min ^a, Hong-Guang Ge ^a, Xiao-Hui Ji ^a, Yue-Fei Bai ^b

PMCID: PMC2970095 PMID: 21577655

Abstract

In the title compound, C₁₆H₁₅BrN₂O₅·2H₂O, the dihedral angle between the two aromatic rings is 2.9 (2)° and an intramolecular O—H⋯N hydrogen bond is observed. One of the water molecule is disordered over two positions, with occupancies of 0.83 (3) and 0.17 (3). In the crystal structure, molecules are linked into a three-dimensional network by intermolecular O—H⋯O, O—H⋯(O,O), O—H⋯N and N—H⋯O hydrogen bonds. π–π interactions involving Br-substituted benzene rings, with a centroid–centroid distance of 3.552 (3) Å are also observed.

Related literature

For related structures, see: Lu et al. (2008a ▶,b ▶,c ▶); Abdul Alhadi et al. (2009 ▶); Mohd Lair et al. (2009 ▶); Narayana et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₆H₁₅BrN₂O₅·2H₂O
M _r = 431.24
Monoclinic,
a = 9.262 (2) Å
b = 8.679 (2) Å
c = 24.289 (5) Å
β = 112.42 (3)°
V = 1804.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 2.32 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T _min = 0.618, T _max = 0.654
14447 measured reflections
3897 independent reflections
1997 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.135
S = 1.02
3897 reflections
261 parameters
20 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536809033522/ci2888sup1.cif

e-65-o2259-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033522/ci2888Isup2.hkl

e-65-o2259-Isup2.hkl^{(191KB, 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
O7—H7B⋯O1	0.85 (5)	2.34 (5)	2.875 (4)	122 (4)
O7—H7B⋯O2	0.85 (5)	2.22 (5)	3.027 (5)	159 (5)
O7—H7A⋯O6A	0.85 (5)	2.06 (2)	2.884 (10)	163 (6)
O6A—H6B⋯O7ⁱ	0.85 (1)	1.91 (4)	2.740 (8)	163 (5)
O6A—H6A⋯O3	0.85 (1)	1.92 (2)	2.715 (6)	154 (4)
N2—H2⋯O5ⁱⁱ	0.90	2.14	3.028 (4)	169
O5—H5⋯O6Bⁱⁱⁱ	0.82	1.85	2.64 (3)	163
O5—H5⋯O6Aⁱⁱⁱ	0.82	1.81	2.618 (5)	166
O1—H1⋯N1	0.82	1.83	2.550 (4)	145

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors thank the Scientific Research Foundation of Shaanxi University of Technology for financial support (project No. SLGQD0708).

supplementary crystallographic information

Comment

Schiff bases and their metal complexes have received much attention in recent years. As part of our investigation on the crystal structures of Schiff bases derived from the condensation of aldehydes with benzohydrazides (Lu et al., 2008a,b,c), we report herein the crystal structure of the title new Schiff base compound.

The title compound (Fig. 1) consists of a Schiff base molecule and two water molecules of crystallization. The bond lengths have normal values (Allen et al., 1987) and are comparable to those observed in related structures (Abdul Alhadi et al., 2009; Mohd Lair et al., 2009; Narayana et al., 2007). The dihedral angle between the two aromatic rings is 2.9 (2)°, indicating that they are approximately coplanar. An intramolecular O—H···N hydrogen bond is observed (Fig. 1).

In the crystal structure, the molecules are linked into layers parallel to the ab direction by intermolecular N—H···O and O—H···O hydrogen bonds (Table 1 and Fig. 2).

Experimental

The title compound was prepared by the Schiff base condensation of 5-bromo-2-hydroxy-3-methoxybenzaldehyde (0.1 mol) and 4-hydroxy-3-methoxybenzohydrazide (0.1 mmol) in 95% ethanol (50 ml). The excess ethanol was removed by distillation. The colourless solid obtained was filtered and washed with ethanol. Single crystals suitable for X-ray diffraction were obatined by slow evaporation of a 95% ethanol solution at room temperature.