Ethyl 2-(3-acetyl-6-methyl-2-oxo-2H-pyran-4-yl­oxy)acetate

Rabnawaz, M.; Benson, S.D.; Khan, B.; Shah, M.R.

doi:10.1107/S1600536810001601

Volume 66
Part 2
Page o397
February 2010

Received 12 January 2010
Accepted 13 January 2010
Online 20 January 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.050
wR = 0.159
Data-to-parameter ratio = 18.3
Details

Ethyl 2-(3-acetyl-6-methyl-2-oxo-2H-pyran-4-yloxy)acetate

Muhammad Rabnawaz,^a Stacy D. Benson,^b Burhan Khan ^a and Muhammad Raza Shah ^a ^*

^aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan, and ^bOklahoma State University, Department of Chemistry, 107 Physical Sciences, Stillwater, OK 74078-3071, USA
Correspondence e-mail: raza_shahm@yahoo.com

The title compound, C₁₂H₁₄O₆, features a roughly planar molecule (r.m.s. deviation for all non-H atoms = 0.287 Å). In the crystal, the molecules are held together by C-HO hydrogen bonds.

Related literature

For the use of dehydroacetic acid as a starting material in the synthesis of heterocyclic ring systems, see: Prakash et al. (2004), and of biologically important molecules such as coumarins, see: Hernandez-Galan et al. (1993).

Experimental

Crystal data

C₁₂H₁₄O₆
M_r = 254.23
Triclinic, $[P \overline 1]$
a = 7.8258 (10) Å
b = 8.2722 (11) Å
c = 10.0838 (13) Å
= 77.374 (7)°
= 77.759 (6)°
= 88.857 (7)°
V = 622.28 (14) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 298 K
0.72 × 0.13 × 0.11 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.925, T_max = 0.988
14279 measured reflections
3039 independent reflections
2330 reflections with I > 2(I)
R_int = 0.036

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.159
S = 1.04
3039 reflections
166 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6A-H6A1O2ⁱ	0.96	2.53	3.462 (2)	165
C5-H5O3Aⁱ	0.93	2.38	3.3053 (19)	174
C2A-H2A1O3Aⁱ	0.97	2.57	3.355 (2)	138
C2E-H2E2O1ⁱⁱ	0.96	2.54	3.484 (3)	169
Symmetry codes: (i) x+1, y, z; (ii) x+1, y+1, z-1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in 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: BT5170 ).

Acknowledgements

The authors thank the Organization for the Prohibition of Chemical Weapons for financial support.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2008). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Hernandez-Galan, R., Salva, J., Massannet, G. M. & Collado, I. G. (1993). Tetrahedron, 49, 1701-1702.
Prakash, O., Kumar, A. & Singh, S. P. (2004). Heterocycles, 63, 1193-1194.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds