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Volume 64 
Part 4 
Page o678  
April 2008  

Received 22 February 2008
Accepted 29 February 2008
Online 7 March 2008


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Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.121
Data-to-parameter ratio = 12.7
Details

2-Phenyl-4-(3,4,5-trimethoxybenzylidene)-1,3-oxazol-5(4H)-one

Yi-Feng Suna,b* and Yi-Ping Cuia

aAdvanced Photonics Center, School of Electronic Science and Engineering, Southeast University, 210096 Nanjing, Jiangsu, People's Republic of China, and bDepartment of Chemistry, Taishan University, 271021 Taian, Shandong, People's Republic of China
Correspondence e-mail: sunyf50@hotmail.com

The title compound, C19H17NO5, was synthesized as part of a continuing project involving the structures of oxazolone derivatives. The molecule adopts a Z configuration about the central olefinic bond. The 2-phenyl ring is slightly twisted out of the plane of the oxazolone ring system by 11.2 (2)°. The crystal structure is stabilized by weak intermolecular C-H...O hydrogen bonds.

Related literature

For background literature, see: Aaglawe et al. (2003[Aaglawe, M. J., Dhule, S. S., Bahekar, S. S., Wakte, P. S. & Shinde, D. B. (2003). J. Korean Chem. Soc. 47, 133-136.]); Grassi et al. (2004[Grassi, G., Foti, F., Risitano, F., Cordaro, M., Nicolo, F. & Bruno, G. (2004). J. Mol. Struct. 698, 81-86.]); Khan et al. (2006[Khan, K. M., Mughal, U. R., Khan, M. T. H., Ullah, Z., Perveen, S. & Choudhary, M. I. (2006). Bioorg. Med. Chem. 14, 6027-6033.]); Song et al. (2001[Song, H.-C., Sun, Y.-F., Li, W.-M., Xu, Z.-L., Zhang, L.-Z. & Cai, Z.-G. (2001). Acta Chim. Sinica, 59, 1563-1565.]). For related structures, see: Sun et al. (2007[Sun, Y.-F., Wang, X.-L., Li, J.-K., Zheng, Z.-B. & Wu, R.-T. (2007). Acta Cryst. E63, o4426.]); Imhof & Garms (2005[Imhof, W. & Garms, S. (2005). Acta Cryst. E61, m1413-m1415.]); Song et al. (2004[Song, H.-C., Wen, H. & Li, W.-M. (2004). Spectrochim. Acta Part A, 60, 1587-1591.]); Vasuki et al. (2001[Vasuki, G., Parthasarathi, V., Ramamurthi, K., Singh, R. M. & Srivastava, A. (2001). Acta Cryst. E57, o120-o121.]).

[Scheme 1]

Experimental

Crystal data

  • C19H17NO5

  • Mr = 339.34

  • Triclinic, [P \overline 1]

  • a = 7.3897 (5) Å

  • b = 8.1532 (6) Å

  • c = 14.0023 (9) Å

  • [alpha] = 86.917 (5)°

  • [beta] = 83.306 (4)°

  • [gamma] = 82.471 (5)°

  • V = 830.02 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 273 (2) K

  • 0.15 × 0.12 × 0.10 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.985, Tmax = 0.990

  • 4665 measured reflections

  • 2904 independent reflections

  • 2056 reflections with I > 2[sigma](I)

  • Rint = 0.020
Refinement

  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.121

  • S = 1.04

  • 2904 reflections

  • 229 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16...O1i 0.93 2.59 3.503 (2) 168
C6-H6...O3ii 0.93 2.62 3.420 (2) 144
Symmetry codes: (i) -x+1, -y, -z; (ii) -x, -y+2, -z.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1997[Bruker (1997). 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2085 ).

Acknowledgements

This project was supported by the Jiangsu Planned Projects for Postdoctoral Research Funds (grant No. 0701001B).

References

Aaglawe, M. J., Dhule, S. S., Bahekar, S. S., Wakte, P. S. & Shinde, D. B. (2003). J. Korean Chem. Soc. 47, 133-136.
Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Grassi, G., Foti, F., Risitano, F., Cordaro, M., Nicolo, F. & Bruno, G. (2004). J. Mol. Struct. 698, 81-86.
Imhof, W. & Garms, S. (2005). Acta Cryst. E61, m1413-m1415.
Khan, K. M., Mughal, U. R., Khan, M. T. H., Ullah, Z., Perveen, S. & Choudhary, M. I. (2006). Bioorg. Med. Chem. 14, 6027-6033.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Song, H.-C., Sun, Y.-F., Li, W.-M., Xu, Z.-L., Zhang, L.-Z. & Cai, Z.-G. (2001). Acta Chim. Sinica, 59, 1563-1565.
Song, H.-C., Wen, H. & Li, W.-M. (2004). Spectrochim. Acta Part A, 60, 1587-1591.
Sun, Y.-F., Wang, X.-L., Li, J.-K., Zheng, Z.-B. & Wu, R.-T. (2007). Acta Cryst. E63, o4426.
Vasuki, G., Parthasarathi, V., Ramamurthi, K., Singh, R. M. & Srivastava, A. (2001). Acta Cryst. E57, o120-o121.

Acta Cryst (2008). E64, o678  [ doi:10.1107/S1600536808005746 ]

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