2-Hydr­oxy-(2-methyl-1H-indol-3-ylmethyl­idene)benzohydrazide ethanol solvate

Wagee A Yehye; Azhar Ariffin; Seik Weng Ng

doi:10.1107/S1600536808011756

. 2008 May 3;64(Pt 6):o960. doi: 10.1107/S1600536808011756

2-Hydroxy-(2-methyl-1H-indol-3-ylmethylidene)benzohydrazide ethanol solvate

Wagee A Yehye ^a, Azhar Ariffin ^a, Seik Weng Ng ^a,^*

PMCID: PMC2961492 PMID: 21202690

Abstract

In the title compound, C₁₇H₁₅N₃O₂·C₂H₆O, Schiff base molecules are linked by a hydroxy–amido hydrogen bond into a helical chain running along the b axis. This chain is consolidated by two other hydrogen bonds; the ethanol solvent molecule is a hydrogen-bond donor to the amide group and a hydrogen-bond acceptor for the indolyl NH group of an adjacent Schiff base molecule.

Related literature

For reports on the medicinal properties of the unsubstituted compound, indol-3-ylmethylidene-2-hydroxybenzohydrazide, see: Alemany et al. (1967 ▶); Fujikawa et al. (1966 ▶); Nakata et al. (1966 ▶); Singh et al. (1984 ▶).

Experimental

Crystal data

C₁₇H₁₅N₃O₂·C₂H₆O
M _r = 339.39
Monoclinic,
a = 7.5907 (1) Å
b = 11.2269 (2) Å
c = 20.3014 (3) Å
β = 91.924 (1)°
V = 1729.11 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 (2) K
0.34 × 0.27 × 0.12 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
20827 measured reflections
3967 independent reflections
2869 reflections with I > 2σ(I)
R _int = 0.056

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.162
S = 1.13
3967 reflections
230 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.30 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 global, I. DOI: 10.1107/S1600536808011756/sg2238sup1.cif

e-64-0o960-sup1.cif^{(18.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011756/sg2238Isup2.hkl

e-64-0o960-Isup2.hkl^{(194.5KB, 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—H1o⋯O2ⁱ	0.84	1.76	2.594 (2)	176
O3—H3o⋯O2	0.84	2.02	2.843 (2)	165
N1—H1n⋯O1	0.88	1.91	2.618 (2)	136
N3—H3n⋯O3ⁱⁱ	0.88	1.96	2.824 (2)	168

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

Acknowledgments

We acknowledge the SAGA grant (06–02-03–0147) for support of this study, and the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

There are no reports of the title Schiff base but there are several reports on the medicinal properties of the unsubstituted compound, indol-3-ylmethylidene-2-hydroxybenzohydrazide (Alemany et al., 1967; Fujikawa et al., 1966; Nakata et al., 1966; Singh et al., 1984). The methyl-substituted title compound (Scheme I, Fig. 1) is a planar molecule that is linked by a hydroxy···amido hydrogen bond into a helical chain that runs along the b-axis of the monoclinic unit cell (Fig. 2). The chain is consolidated by two other hydrogen bonds: the ethanol molecule is hydrogen-bond donor to the amido unit well as hydrogen-bond acceptor to the amino_indolyl unit of adjacent Schiff bases.

Experimental

2-Hydroxybenzohyrazide (0.60 g, 4 mmol) and 2-methyl-1H-indole-3-carboxaldehyde (0.63 g, 4 mmol) were heated in ethanol (30 ml) for 3 h. The solvent was removed by evaporation and the light brown product recrystallized from ethanol.