Ethyl 1-[(4-acetyl-2-methoxy­phen­oxy)meth­yl]cyclo­propane-1-carboxyl­ate

Tang, T.; Gao, L.; Jia, H.-S.; Wu, Y.-M.; Ma, H.-F.

doi:10.1107/S1600536809000956

Volume 65
Part 2
Page o305
February 2009

Received 9 December 2008
Accepted 8 January 2009
Online 14 January 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.062
wR = 0.168
Data-to-parameter ratio = 14.2
Details

Ethyl 1-[(4-acetyl-2-methoxyphenoxy)methyl]cyclopropane-1-carboxylate

Ting Tang,^a Lei Gao,^a Hong-Sheng Jia,^b Ya-Ming Wu ^c and Hong-Fei Ma ^a ^*

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China,^bDepartment of Chemical Engineering, Chien-shlung Institute of Technology, Taicang 215411, People's Republic of China, and ^cDepartment of Applied Chemistry, Nanjing College of Chemical Technology, No. 625 Geguan Road, Dachang, Nanjing 210048, People's Republic of China
Correspondence e-mail: mhf2356@yahoo.com.cn

In the title compound, C₁₆H₂₀O₅, the dihedral angle between the planar rings, viz. benzene and cyclopropane, is 52.1 (2)°. Molecules are connected in the crystal via weak intermolecular C-HO hydrogen bonds, forming chains in the [001] direction.

Related literature

For details of the synthesis, see: Chen (2008).

Experimental

Crystal data

C₁₆H₂₀O₅
M_r = 292.32
Monoclinic, P 2₁ /c
a = 12.663 (3) Å
b = 8.5020 (17) Å
c = 14.676 (3) Å
= 107.25 (3)°
V = 1509.0 (5) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 (2) K
0.20 × 0.10 × 0.10 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.981, T_max = 0.991
2874 measured reflections
2732 independent reflections
1473 reflections with I > 2(I)
R_int = 0.039
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(F²)] = 0.062
wR(F²) = 0.168
S = 0.93
2732 reflections
193 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C7-H7AO1ⁱ	0.93	2.56	3.329 (4)	140
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1985); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: BH2213 ).

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Chen, G. P. (2008). Advenchen Laboratories, LLC, USA. WO Patent No. 2008112407.
Enraf-Nonius (1985). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds