3-Amino-N′-(2-oxoindolin-3-yl­idene)benzohydrazide

Rifat Ara Jamal; Uzma Ashiq; Sammer Yousuf; Qurrat ul Ain

doi:10.1107/S1600536811029242

. 2011 Jul 30;67(Pt 8):o2166. doi: 10.1107/S1600536811029242

3-Amino-N′-(2-oxoindolin-3-ylidene)benzohydrazide

Rifat Ara Jamal ^a,^*, Uzma Ashiq ^a, Sammer Yousuf ^b, Qurrat ul Ain ^a

PMCID: PMC3213601 PMID: 22091178

Abstract

The title compound, C₁₅H₁₂N₄O₂, contains two substituted benzohydrazide and indole rings linked via a C=N double bond. The dihedral angle between the benzene ring and the indole ring system is 11.38 (10)°. The molecular structure is stabilized by an intramolecular N—H⋯O hydrogen bond, forming a six-membered ring. The crystal structure is consolidated by intermolecular N—H⋯O and C—H⋯O interactions, which result in sheets.

Related literature

For the biological activity of related compounds, see: Ashiq et al. (2008 ▶); Maqsood et al. (2006 ▶); Sarangapani & Reddy (1994 ▶). For related structures, see: Bai et al. (2006 ▶); Yang & Pan (2004 ▶).

Experimental

Crystal data

C₁₅H₁₂N₄O₂
M _r = 280.29
Monoclinic,
a = 8.8036 (8) Å
b = 8.9040 (7) Å
c = 17.0732 (14) Å
β = 92.335 (2)°
V = 1337.21 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.17 × 0.17 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.984, T _max = 0.989
7637 measured reflections
2491 independent reflections
1551 reflections with I > 2σ(I)
R _int = 0.047

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.122
S = 0.99
2491 reflections
198 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029242/pv2431sup1.cif

e-67-o2166-sup1.cif^{(18KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029242/pv2431Isup2.hkl

e-67-o2166-Isup2.hkl^{(122.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029242/pv2431Isup3.cml

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
N1—H1A⋯O2ⁱ	0.86	2.02	2.785 (2)	148
N3—H3A⋯O1	0.86	2.09	2.757 (2)	133
N4—H4C⋯N2ⁱⁱ	0.86 (2)	2.61 (2)	3.423 (3)	158 (2)
C12—H12A⋯O1ⁱⁱⁱ	0.93	2.59	3.424 (3)	149

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

Acknowledgments

The authors are thankful to the Higher Education Commission (HEC) Pakistan for financial support under the National Research Grants Program for Universities (grant No. 20–1862/R&D/10).

supplementary crystallographic information

Comment

Compounds containing hydrazide moiety have been revealed to exhibit a wide variety of interesting biological properties (Ashiq et al. 2008; Maqsood et al. 2006). In a quest to expand and further explore the biological significance of hydrazides, we have undertken a task to synthesize new Schiff bases of isatin with hydrazides. Isatins are very important compounds due to their antifungal properties (Sarangapani & Reddy, 1994). In this article we report the synthesis and crystal structure of the title compound.

The title molecule (Fig. 1) consists of substituted benzohydrazide and indole rings linked by C═N bond. The dihedral angle between the two substituted benzene (C10—C15) and indole ring (N1/C1—C8) is 11.38 (10)°. The bond lengths and angles are in normal range as in other structurally related compounds (Bai et al. 2006; Yang & Pan, 2004). The geometry of the molecule is stabilized by N3—H3A···O1 intramolecular hydrogen bond resulting in a six membered ring. In the crystal structure, the molecules are linked to form two-dimensional sheets via N1—H1A···O2, N4—H4C···N2 and C12—H12A···O1 intermolecular hydrogen bonds (Tab. 1 & Fig. 2).

Experimental

To a solution of 2,3-indolinedione (10 mmol, 1.47 g) in 15 ml of ethanol with a few drops of glacial acetic acid and 3-aminobenzohydrazide (10 mmol, 1.51 g) in 15 ml ethanol were added. The mixture was refluxed for 2 h and a solid was obtained upon removal of the solvent by rotary evaporation. The resulting solid was washed with ethanol to afford the title compound (yield 75%). The crystals of the title compound suitable for XRD analysis were grown from a mixture of ethanol and methanol (1:1) by slow evaporation at room temperature.