3-(2-Ethyl-2-phenyl­hydrazin-1-yl­idene)indolin-2-one

Ashiq, U.; Jamal, R.A.; Ismail, H.; Khan, K.M.; Yousuf, S.

doi:10.1107/S1600536812047988

Volume 68
Part 12
Page o3473
December 2012

Received 20 November 2012
Accepted 21 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.003 Å
R = 0.047
wR = 0.116
Data-to-parameter ratio = 13.5
Details

3-(2-Ethyl-2-phenylhydrazin-1-ylidene)indolin-2-one

Uzma Ashiq,^a ^* Rifat Ara Jamal,^a Hina Ismail,^a Khalid Mohammed Khan ^b and Sammer Yousuf ^b ^*

^aDepartment of Chemistry, University of Karachi, Karachi 75270, Pakistan, and ^bH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: uzzmma@hotmail.com, dr.sammer.yousuf@gmail.com

In the title compound, C₁₆H₁₅N₃O, the dihedral angle between the indole ring system (r.m.s. deviation = 0.020 Å) and the phenyl ring is 14.49 (9)°. The molecular conformation is supported by an intramolecular C-HO interaction, which closes an S(7) ring. In the crystal, inversion dimers linked by pairs of N-HO hydrogen bonds generate R₂²(8) loops.

Related literature

For a related structure, see: Jamal et al. (2011). For background to Schiff bases, see: Chaluvaraju & Zaranappa (2011); Khan et al. (2009).

Experimental

Crystal data

C₁₆H₁₅N₃O
M_r = 265.31
Monoclinic, P 2₁ /c
a = 9.463 (2) Å
b = 17.303 (4) Å
c = 8.5403 (18) Å
= 104.427 (5)°
V = 1354.3 (5) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 273 K
0.35 × 0.18 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000) T_min = 0.971, T_max = 0.995
7875 measured reflections
2448 independent reflections
1783 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.116
S = 1.08
2448 reflections
181 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15AO1	0.97	2.21	2.916 (2)	128
N1-H1AO1ⁱ	0.86	1.99	2.844 (2)	172
Symmetry code: (i) -x+1, -y, -z-1.

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: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6996 ).

Acknowledgements

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).

References

Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chaluvaraju, K. C. & Zaranappa (2011). Res. J. Pharm. Biol. Chem. Sci. 2, 541-546.
Jamal, R. A., Ashiq, U., Yousuf, S. & Ain, Q. ul (2011). Acta Cryst. E67, o2166.
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds