N′-(2,4-Dimethoxy­benzyl­idene)-3,4,5-trihydroxy­benzohydrazide ethanol solvate

Abeer A Alhadi; Siti Munirah Saharin; Hapipah Mohd Ali; Ward T Robinson; Mahmood A Abdulla

doi:10.1107/S1600536809018947

. 2009 May 23;65(Pt 6):o1373. doi: 10.1107/S1600536809018947

N′-(2,4-Dimethoxybenzylidene)-3,4,5-trihydroxybenzohydrazide ethanol solvate

Abeer A Alhadi ^a, Siti Munirah Saharin ^a, Hapipah Mohd Ali ^a,^*, Ward T Robinson ^a, Mahmood A Abdulla ^b

PMCID: PMC2969598 PMID: 21583222

Abstract

The title compound, C₁₆H₁₆N₂O₆·C₂H₅OH, was synthesized from 3,4,5-trihydroxybenzoylhydrazide and 2,4-dimethoxybenzaldehyde in ethanol. The compound is not planar, with the two aromatic planes of the two aromatic rings twisted by 15.6 (1)°. The hydroxy groups are involved in both intramolecular O—H⋯O and intermolecular O—H⋯N and O—H⋯O hydrogen bonds and a C—H⋯O interaction also occurs.

Related literature

For related compounds, see Abdul Alhadi et al. (2009 ▶). For the parent N′-(2-hydroxybenzylidene)benzohydrazide, see Lyubchova et al. (1995 ▶).

Experimental

Crystal data

C₁₆H₁₆N₂O₆·C₂H₆O
M _r = 378.38
Monoclinic,
a = 7.8347 (1) Å
b = 17.5412 (3) Å
c = 13.0230 (2) Å
β = 93.936 (1)°
V = 1785.53 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.31 × 0.16 × 0.12 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.967, T _max = 0.987
19580 measured reflections
5188 independent reflections
3586 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.121
S = 1.02
5188 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018947/hg2510sup1.cif

e-65-o1373-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018947/hg2510Isup2.hkl

e-65-o1373-Isup2.hkl^{(254.1KB, 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
O2—H2⋯O3	0.84	2.54	2.9325 (13)	109
O3—H3⋯O2	0.84	2.54	2.9325 (13)	110
O4—H4⋯O3	0.84	2.25	2.7009 (14)	114
N1—H1′⋯O7ⁱ	0.88	2.04	2.8844 (15)	160
O2—H2⋯O1ⁱⁱ	0.84	1.86	2.6871 (13)	170
O2—H2⋯N2ⁱⁱ	0.84	2.57	2.9293 (15)	107
O3—H3⋯O1ⁱⁱ	0.84	1.88	2.7200 (13)	177
O4—H4⋯O6ⁱⁱⁱ	0.84	2.14	2.7366 (14)	127
C14—H14⋯O2^iv	0.95	2.42	3.3539 (17)	167

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

Acknowledgments

The authors thank the University of Malaya for funding this study (Science Fund Grant 12-0-03-2031, 12-02-03-2051 and PJP FS350-2008)

supplementary crystallographic information

Experimental

A mixture of 3,4,5-trihydroxybenzoylhydrazide and 2,4-dimethoxybenzaldehyde were heated in ethanol (50 ml) for 12 h. The yellow crystals were obtained by recrystallization from ethanol.