3,4-Dihydr­oxy-N′-(2-hydroxy­benzyl­idene)benzohydrazide–methanol–water (2/1/3)

Hong-Bo Ma; Shan-Shan Huang; Yun-Peng Diao

doi:10.1107/S1600536807065038

. 2007 Dec 6;64(Pt 1):o210. doi: 10.1107/S1600536807065038

3,4-Dihydroxy-N′-(2-hydroxybenzylidene)benzohydrazide–methanol–water (2/1/3)

Hong-Bo Ma ^a, Shan-Shan Huang ^b,^*, Yun-Peng Diao ^b,^*

PMCID: PMC2915271 PMID: 21200776

Abstract

The asymmetric unit of the title compound, C₁₄H₁₂N₂O₄·0.5CH₄O·1.5H₂O, consists of two Schiff base molecules, three water molecules and one methanol molecule. The dihedral angle between the two benzene rings is 7.8 (2)° in one of the molecules and 4.0 (2)° in the other. Intramolecular O—H⋯O and O—H⋯N hydrogen bonds are observed. Molecules are linked into a three-dimensional network by O—H⋯O and N—H⋯O intermolecular hydrogen bonds.

Related literature

For the biological properties of Schiff base compounds, see: Brückner et al. (2000 ▶); Harrop et al. (2003 ▶); Ren et al. (2002 ▶). For related structures, see: Diao (2007 ▶); Diao et al. (2007 ▶); Huang et al. (2007 ▶); Li et al. (2007 ▶).

Experimental

Crystal data

C₁₄H₁₂N₂O₄·0.5CH₄O·1.5H₂O
M _r = 315.30
Triclinic,
a = 10.707 (2) Å
b = 11.994 (2) Å
c = 14.103 (3) Å
α = 111.56 (3)°
β = 103.13 (3)°
γ = 104.72 (3)°
V = 1522.2 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 298 (2) K
0.17 × 0.15 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.982, T _max = 0.984
9348 measured reflections
6429 independent reflections
2812 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.055
wR(F ²) = 0.144
S = 0.97
6429 reflections
438 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2000 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807065038/ci2538sup1.cif

e-64-0o210-sup1.cif^{(23.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065038/ci2538Isup2.hkl

e-64-0o210-Isup2.hkl^{(314.6KB, 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
O10—H10B⋯O7ⁱ	0.85 (2)	1.96 (1)	2.793 (3)	168 (3)
O10—H10A⋯O6ⁱⁱ	0.85 (1)	2.10 (1)	2.938 (3)	173 (3)
O11—H11A⋯O8	0.85 (2)	2.09 (1)	2.925 (3)	170 (3)
O12—H12A⋯O11ⁱⁱⁱ	0.85 (2)	1.94 (1)	2.770 (3)	165 (3)
N1—H1A⋯O10	0.91 (3)	1.96 (3)	2.844 (3)	167 (3)
O12—H12B⋯O2^iv	0.85 (2)	2.04 (1)	2.889 (3)	177 (3)
O11—H11B⋯O9^v	0.85 (3)	1.95 (3)	2.765 (3)	162 (3)
N3—H3⋯O12	0.90 (3)	1.96 (3)	2.845 (3)	165 (3)
O8—H8⋯N4	0.82	1.87	2.589 (3)	146
O6—H6⋯O9^vi	0.82	2.04	2.834 (3)	161
O5—H5⋯O3^vi	0.82	1.86	2.670 (3)	170
O4—H4⋯N2	0.82	1.84	2.561 (3)	146
O2—H2⋯O1	0.82	2.29	2.725 (3)	114
O2—H2⋯O11^vii	0.82	1.93	2.703 (3)	158
O1—H1⋯O7^vii	0.82	1.88	2.695 (3)	172

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

Acknowledgments

This project is supported by a research grant from Dalian Medical University.

supplementary crystallographic information

Comment

Schiff base compounds have received much attention in recent years. Some of the complexes have been found to have pharmacological and antitumor properties (Brückner et al., 2000; Harrop et al., 2003; Ren et al., 2002). As part of our research programme on the structure of Schiff base compounds (Diao, 2007; Diao et al., 2007; Li et al., 2007; Huang et al., 2007), we report here the structure of the title compound.

The asymmetric unit of the title compound consists of two Schiff base molecules, three water molecules and one methanol molecule (Fig. 1). The corresponding bond lengths and angles in the two Schiff base molecules are nearly identical. The dihedral angle between the C1—C6 and C9—C14 benzene rings is 7.8 (2)° and that between the C15—C20 and C23—C28 benzene rings is 4.0 (2)°. The structure of each molecule is stabilized by O—H···O and O—H···N intramolecular hydrogen bonds.

In the crystal structure, the molecules are linked through intermolecular O—H···O and N—H···O hydrogen bonds (Table 1), forming a three-dimensional network (Fig. 2).

Experimental

Salicylaldehyde (1.0 mmol, 122.1 mg) and 3,4-dihydroxybenzoic acid hydrazide (1.0 mmol, 168.2 mg) were dissolved in a methanol solution (70 ml). The mixture was stirred at room temperature for 1 h and filtered. After keeping the filtrate in air for a week, yellow block-shaped crystals were formed.