trans-4-(1-Naphth­yl)-2-oxo-1,3-oxazolidine-5-carboxylic acid

Yang, J.-Y.; Ming, Z.-H.; An, J.; Hua, Q.-L.; Lu, L.-Q.

doi:10.1107/S1600536808019132

Volume 64
Part 8
Page o1484
August 2008

Received 25 May 2008
Accepted 24 June 2008
Online 12 July 2008

Key indicators
Single-crystal X-ray study
T = 292 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.093
Data-to-parameter ratio = 12.7
Details

trans-4-(1-Naphthyl)-2-oxo-1,3-oxazolidine-5-carboxylic acid

Jiao-Yan Yang,^a Zhi-Hui Ming,^b Jing An,^b Qiu-Lin Hua ^b and Liang-Qiu Lu ^b ^*

^aCollege of Life Sciences, Central China Normal University, Wuhan 430079, People's Republic of China, and ^bKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
Correspondence e-mail: luliangqiu@mails.ccnu.edu.cn

The crystal structure of the title compound, C₁₄H₁₁NO₄, is influenced by N-HO and O-HO hydrogen bonds, linking molecules into one-dimensional tapes running along the [010] direction.

Related literature

For general backgroud regarding the title compound, see: Lu et al. (2008). For patterns in hydrogen bonding, see: Bernstein et al. (1995). For related literature, see: Barbachyn & Ford (2003); Evans (1982); Mukhtar & Wright (2005).

Experimental

Crystal data

C₁₄H₁₁NO₄
M_r = 257.24
Orthorhombic, P b c a
a = 8.7159 (17) Å
b = 12.817 (3) Å
c = 20.737 (4) Å
V = 2316.6 (8) Å³
Z = 8
Mo K radiation
= 0.11 mm^-1
T = 292 (2) K
0.47 × 0.38 × 0.35 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: none
12484 measured reflections
2266 independent reflections
2008 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.093
S = 1.04
2266 reflections
178 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.19 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1AO4ⁱ	0.94 (2)	1.72 (2)	2.6591 (15)	174 (2)
N1-H1O2ⁱⁱ	0.834 (17)	2.247 (17)	3.0097 (18)	152.0 (15)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BG2191 ).

Acknowledgements

We thank Dr Xiang-Gao Meng for the X-ray data collection.

References

Barbachyn, M. R. & Ford, C. W. (2003). Angew. Chem. Int. Ed. 42, 2010-2023.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Evans, D. A. (1982). Aldrichimica Acta, 15, 23-32.
Lu, L. Q., Cao, Y. J., Liu, X. P., An, J., Yao, C. J., Ming, Z. H. & Xiao, W. J. (2008). J. Am. Chem. Soc. 130, 6946-6948.
Mukhtar, T. A. & Wright, G. D. (2005). Chem. Rev. 105, 529-542.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.

organic compounds