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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 [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.116
Data-to-parameter ratio = 13.5
Details
Open access

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

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-H...O interaction, which closes an S(7) ring. In the crystal, inversion dimers linked by pairs of N-H...O hydrogen bonds generate R22(8) loops.

Related literature

For a related structure, see: Jamal et al. (2011[Jamal, R. A., Ashiq, U., Yousuf, S. & Ain, Q. ul (2011). Acta Cryst. E67, o2166.]). For background to Schiff bases, see: Chaluvaraju & Zaranappa (2011[Chaluvaraju, K. C. & Zaranappa (2011). Res. J. Pharm. Biol. Chem. Sci. 2, 541-546.]); Khan et al. (2009[Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15N3O

  • Mr = 265.31

  • Monoclinic, P 21 /c

  • a = 9.463 (2) Å

  • b = 17.303 (4) Å

  • c = 8.5403 (18) Å

  • [beta] = 104.427 (5)°

  • V = 1354.3 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.971, Tmax = 0.995

  • 7875 measured reflections

  • 2448 independent reflections

  • 1783 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.116

  • S = 1.08

  • 2448 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15A...O1 0.97 2.21 2.916 (2) 128
N1-H1A...O1i 0.86 1.99 2.844 (2) 172
Symmetry code: (i) -x+1, -y, -z-1.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CSD] [CrossRef] [details]
Khan, K. M., Khan, M., Ali, M., Taha, M., Rasheed, S., Perveen, S. & Choudhary, M. I. (2009). Bioorg. Med. Chem. 17, 7795-7801.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3473  [ doi:10.1107/S1600536812047988 ]

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