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Volume 68 
Part 11 
Page o3224  
November 2012  

Received 16 October 2012
Accepted 23 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.074
wR = 0.225
Data-to-parameter ratio = 17.4
Details
Open access

5-(Diphenylmethylidene)pyrrolidin-2-one

aDepartment of Applied Cosmetology and Graduate Institute of Cosmetic Science, Hungkuang University, Taichung 433, Taiwan, and bDepartment of Chemistry, National Chung Hsing University, Taichung 402, Taiwan
Correspondence e-mail: mjchen@sunrise.hk.edu.tw

In the title compound, C17H15NO, the dihedral angle between the phenyl rings is 80.1 (2)°. In the crystal, molecules are linked by pairs of N-H...O hydrogen bonds, forming inversion dimers.

Related literature

The title compound is a pyrrolidin-2-one derivative. For the preparation of related structures, see: Fujihara & Tomioka (1999[Fujihara, H. & Tomioka, K. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 2377-2382.]); Enders & Han (2008[Enders, D. & Han, J. (2008). Tetrahedron Asymmetry, 19, 1367-1371.]). For a related structure containing intermolecular N-H...O=C hydrogen bonds, see: Asiri et al. (2012[Asiri, A. M., Zayed, M. E. M., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2020.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15NO

  • Mr = 249.30

  • Triclinic, [P \overline 1]

  • a = 7.135 (2) Å

  • b = 7.885 (2) Å

  • c = 12.184 (4) Å

  • [alpha] = 89.76 (3)°

  • [beta] = 75.09 (3)°

  • [gamma] = 85.65 (2)°

  • V = 660.4 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 293 K

  • 0.70 × 0.50 × 0.35 mm

Data collection
  • Agilent Xcalibur (Sapphire3, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.542, Tmax = 1.000

  • 5549 measured reflections

  • 2999 independent reflections

  • 1951 reflections with I > 2[sigma](I)

  • Rint = 0.052

Refinement
  • R[F2 > 2[sigma](F2)] = 0.074

  • wR(F2) = 0.225

  • S = 1.06

  • 2999 reflections

  • 172 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N-H0A...Oi 0.86 2.11 2.921 (2) 157
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: LH5547 ).


Acknowledgements

We gratefully acknowledge financial support in part from the National Science Council, Taiwan (NSC 99-2119-M-241- 001-MY2). Helpful comments from the reviewers were also greatly appreciated.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Asiri, A. M., Zayed, M. E. M., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o2020.  [CSD] [CrossRef] [details]
Enders, D. & Han, J. (2008). Tetrahedron Asymmetry, 19, 1367-1371.  [ISI] [CrossRef] [ChemPort]
Fujihara, H. & Tomioka, K. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 2377-2382.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3224  [ doi:10.1107/S1600536812043851 ]

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