5-(Diphenyl­methyl­idene)pyrrolidin-2-one

Hsu, T.-F.; Chen, Y.-R.; Huang, B.-H.; Chen, M.-J.

doi:10.1107/S1600536812043851

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 (C-C) = 0.003 Å
R = 0.074
wR = 0.225
Data-to-parameter ratio = 17.4
Details

5-(Diphenylmethylidene)pyrrolidin-2-one

Tzu-Fang Hsu,^a Yan-Ru Chen,^a Bor-Hunn Huang ^b and Ming-Jen Chen ^a ^*

^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-HO 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); Enders & Han (2008). For a related structure containing intermolecular N-HO=C hydrogen bonds, see: Asiri et al. (2012).

Experimental

Crystal data

C₁₇H₁₅NO
M_r = 249.30
Triclinic, $[P \overline 1]$
a = 7.135 (2) Å
b = 7.885 (2) Å
c = 12.184 (4) Å
= 89.76 (3)°
= 75.09 (3)°
= 85.65 (2)°
V = 660.4 (4) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.542, T_max = 1.000
5549 measured reflections
2999 independent reflections
1951 reflections with I > 2(I)
R_int = 0.052

Refinement

R[F² > 2(F²)] = 0.074
wR(F²) = 0.225
S = 1.06
2999 reflections
172 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N-H0AOⁱ	0.86	2.11	2.921 (2)	157
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: 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.
Enders, D. & Han, J. (2008). Tetrahedron Asymmetry, 19, 1367-1371.
Fujihara, H. & Tomioka, K. (1999). J. Chem. Soc. Perkin Trans. 1, pp. 2377-2382.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds