N-Acetyl-2-hydroxy-N′-[methoxy(1-methylindol-2-yl)methyl]benzohydrazide

Wagee A Yehye; Noorsaadah Abdul Rahman; Azhar Ariffin; Seik Weng Ng

doi:10.1107/S1600536808026846

. 2008 Aug 23;64(Pt 9):o1824. doi: 10.1107/S1600536808026846

N-Acetyl-2-hydroxy-N′-[methoxy(1-methylindol-2-yl)methyl]benzohydrazide

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

PMCID: PMC2960481 PMID: 21201799

Abstract

In the crystal structure of the title Schiff-base, C₂₀H₂₁N₃O₄, the amino group forms an N—H⋯O hydrogen bond to the acetyl group of an adjacent molecule, forming a zigzag chain. The 2-hydroxy group is internally hydrogen bonded to the amido group though an O—H⋯O hydrogen bond.

Related literature

For medicinal uses of the precursor Schiff base, see: Jin et al. (2006 ▶); Joshi et al. (2008 ▶); Szczepankiewicz et al. (2001 ▶).

Experimental

Crystal data

C₂₀H₂₁N₃O₄
M _r = 367.40
Monoclinic,
a = 11.0075 (3) Å
b = 10.5197 (3) Å
c = 15.4479 (4) Å
β = 93.967 (2)°
V = 1784.51 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 (2) K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
16316 measured reflections
4072 independent reflections
2646 reflections with I > 2σ(I)
R _int = 0.065

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.120
S = 1.02
4072 reflections
255 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.26 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/S1600536808026846/tk2298sup1.cif

e-64-o1824-sup1.cif^{(20.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026846/tk2298Isup2.hkl

e-64-o1824-Isup2.hkl^{(199.6KB, 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
O1—H1o⋯O2	0.87 (1)	1.81 (2)	2.599 (2)	150 (3)
N1—H1n⋯O3ⁱ	0.85 (1)	2.01 (1)	2.812 (2)	157 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the University of Malaya for supporting this study (grant No. FS338/2008 A).

supplementary crystallographic information

Comment

The Schiff base, N'-[(1-methyl-1H-indol-2-yl)methylene]-2-hydroxybenzohydrazide, exhibits useful medicinal properties (Jin et al., 2006; Joshi et al., 2008; Szczepankiewicz et al., 2001). When dissolved in acetic anhydride, the compound undergoes a reaction to yield the title compound, (I), Fig. 1. Essentially, a mole of methyl acetate has been added across the carbon-nitrogen double-bond. In the crystal structure of (I), the amino group forms an N–H···O hydrogen bond to the acetyl group of an adjacent molecule to result in a zigzag chain that runs along the b-axis of the orthorhombic unit cell, Table 1. The 2-hydroxy group is internally hydrogen bonded to the amido group though an O–H···O hydrogen bond, Table 1.

Experimental

2-Hydroxybenzohydrazide was condensed with 1-methylindole-3-carboxaldehyde to yield the corresponding Schiff base. To N'-[(1-methyl-1H-indol-2-yl)methylene]-2-hydroxybenzohydrazide (0.88 g, 3 mmol) was added acetic anhydride (10 ml). The mixture was heated to 398–403 K until the reactants dissolved completely. After 2 h of heating, the mixture was cooled and then treated with ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was separated and dried over anhydrous sodium sulfate. The solvent was evaporated and the resulting solid was recrystallized from methanol to give (I) as colorless crystals.