4-[(2-Methyl-5-oxo-4,5-dihydro-1,3-oxazol-4-yl­idene)meth­yl]phenyl acetate

Guo, P.; Wang, C.; Chen, J.; Mou, D.

doi:10.1107/S1600536809032243

Volume 65
Part 9
Page o2215
September 2009

Received 2 June 2009
Accepted 14 August 2009
Online 22 August 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.061
wR = 0.164
Data-to-parameter ratio = 14.8
Details

4-[(2-Methyl-5-oxo-4,5-dihydro-1,3-oxazol-4-ylidene)methyl]phenyl acetate

Pengran Guo,^a Chang Wang,^b Jianghan Chen ^b and Dehai Mou ^b ^*

^aSchool of Environmental Science and Engineering, Sun Yat-Sen University, Guangzhou 510275, People's Republic of China, and ^bGuangdong Provincial Key Laboratory of Emergency Testing for Dangerous Chemicals, China National Analytical Center, Guangzhou 510070, People's Republic of China
Correspondence e-mail: guopengran@gmail.com

In the title compound, C₁₃H₁₁NO₄, an intramolecular C-HN interaction helps to establish the conformation. In the crystal, two C-HO contacts stack adjacent molecules into a one-dimensional double chain running in the a-axis direction.

Related literature

The title compound is an important medical intermediate, see: Baker (1951).

Experimental

Crystal data

C₁₃H₁₁NO₄
M_r = 245.23
Triclinic, $[P \overline 1]$
a = 5.5802 (15) Å
b = 7.446 (2) Å
c = 15.012 (4) Å
= 94.322 (4)°
= 93.156 (4)°
= 108.136 (4)°
V = 589.1 (3) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 293 K
0.14 × 0.13 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SAINT-Plus; Bruker, 2003) T_min = 0.985, T_max = 0.992
3324 measured reflections
2264 independent reflections
1707 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.164
S = 1.04
2264 reflections
153 parameters
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C4-H4N1	0.93	2.45	3.098 (4)	127
C7-H7O2ⁱ	0.93	2.53	3.417 (4)	160
C13-H13BO4ⁱⁱ	0.96	2.50	3.382 (4)	152
Symmetry codes: (i) -x+1, -y+1, -z; (ii) x+1, y, z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2130 ).

Acknowledgements

This work was supported by Guangdong Provincial Key Laboratory of Emergency Testing for Dangerous Chemicals, China National Analytical Center (Guangzhou), People's Republic of China.

References

Baker, L. E. (1951). J. Biol. Chem. 193, 809-819.
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsion, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds