N′-(2-Hydr­oxy-5-nitro­benzyl­idene)-2-(1H-indol-3-yl)acetohydrazide

Subramaniam Puvaneswary; Hapipah M Ali; Ward T Robinson; Seik Weng Ng

doi:10.1107/S1600536808026044

. 2008 Aug 16;64(Pt 9):o1777. doi: 10.1107/S1600536808026044

N′-(2-Hydroxy-5-nitrobenzylidene)-2-(1H-indol-3-yl)acetohydrazide

Subramaniam Puvaneswary ^a, Hapipah M Ali ^a, Ward T Robinson ^a, Seik Weng Ng ^a,^*

PMCID: PMC2960495 PMID: 21201757

Abstract

The molecule of the title compound, C₁₇H₁₄N₄O₄, uses its amide –NH– group to form a hydrogen bond to the amido –C(=O)– group of an adjacent molecule to furnish a linear chain structure. The hydroxy group forms an intramolecular hydrogen bond; the indolyl –NH– unit does not engage in any strong hydrogen-bonding interactions.

Related literature

For similar compounds, see: Martin Reyes et al. (1986 ▶); Martin Zarza et al. (1989 ▶).

Experimental

Crystal data

C₁₇H₁₄N₄O₄
M _r = 338.32
Orthorhombic,
a = 9.5387 (2) Å
b = 11.2724 (3) Å
c = 29.7796 (7) Å
V = 3202.0 (1) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 100 (2) K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: none
47721 measured reflections
3679 independent reflections
2059 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.160
S = 1.02
3679 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 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/S1600536808026044/bq2091sup1.cif

e-64-o1777-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026044/bq2091Isup2.hkl

e-64-o1777-Isup2.hkl^{(180.5KB, 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⋯N2	0.84	1.85	2.583 (2)	146
N3—H3n⋯O4ⁱ	0.88	2.07	2.827 (2)	144

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Science Fund (12–02-03–2031, 12–02-03–2051) and the University of Malaya (PJP) for supporting this study. We are grateful to the University of Malaya for the purchase of the diffractometer.

supplementary crystallographic information

Comment

There are many examples of Schiff bases derived from the condensation of salicylaldehyde and substituted salicyldehydes with hydrazides such as the ones reported by Martin Reyes et al. (1986) and Martin Zarza et al. (1989). The title compound (Fig. 1) is another example. The molecule uses its amido –NH– group to form a hydrogen bond to the amido –C(=O)– group of an adjacent molecule to furnish a linear chain structure.

Experimental

The Schiff base was prepared by refluxing a solution of indole-3-acetic acid hydrazide (0.34 g, 1.80 mmol) and 5-nitrosalicylaldehyde (0.30 g, 1.80 mmol) in acidified ethanol (25 ml) for 2 h. On cooling to room temperature, yellow crystals separated out.