1-(2-Hydr­oxy-3,4-dimethoxy­phen­yl)-2-(4-methoxy­phen­yl)ethanone

Xiao, Z.-P.; Xiao, H.-Y.

doi:10.1107/S1600536808036258

Volume 64
Part 12
Page o2324
December 2008

Received 19 October 2008
Accepted 6 November 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.071
wR = 0.215
Data-to-parameter ratio = 12.9
Details

1-(2-Hydroxy-3,4-dimethoxyphenyl)-2-(4-methoxyphenyl)ethanone

Zhu-Ping Xiao ^a ^* and He-Ying Xiao ^a

^aCollege of Chemistry & Chemical Engineering, Jishou University, Jishou 416000, People's Republic of China
Correspondence e-mail: xiaozhuping2005@163.com

In the title compound, C₁₇H₁₈O₅, the pyrogallol group is almost coplanar with the mean plane of the attached carbonyl group [dihedral angle of 1.95 (13)°] and makes a dihedral angle of 56.01 (10)° with the other benzene ring. Of the three methoxy groups, only one is significantly twisted relative to its attached benzene ring [C-O-C-C torsion angles of 4.0 (5), 3.9 (6) and -106.3 (4)°]. Intramolecular O-HO and C-HO hydrogen bonds help to establish the conformation, and the packing is consolidated by C-HO interactions and [pi] - [pi] stacking interactions [centroid-centroid separation = 3.735 (2) Å].

Related literature

For background on the properties of deoxybenzoins, see: Kiuchi et al. (1990); Li et al. (2008); Niwa et al. (1999); Papoutsi et al. (2007); Parmar et al. (1996); Sanduja et al. (1985); Xiao et al. (2008); Xiao, Fang et al. (2007); Xiao, Shi et al. (2007).

Experimental

Crystal data

C₁₇H₁₈O₅
M_r = 302.31
Monoclinic, P 2₁ /c
a = 14.431 (3) Å
b = 14.073 (3) Å
c = 7.4610 (15) Å
= 92.86 (3)°
V = 1513.3 (5) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 (2) K
0.30 × 0.30 × 0.30 mm

Data collection

Enraf-Nonius CAD-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.971, T_max = 0.971
2893 measured reflections
2667 independent reflections
1543 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.071
wR(F²) = 0.215
S = 1.03
2667 reflections
206 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H18O1	0.89 (4)	1.78 (4)	2.583 (4)	148 (4)
C15-H15AO2	0.96	2.56	3.086 (5)	115
C11-H11O3ⁱ	0.93	2.51	3.259 (4)	138
C17-H17BO4ⁱⁱ	0.96	2.59	3.315 (6)	133
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf-Nonius, 1989); 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: HB2823 ).

Acknowledgements

The work was financed by a grant (No. JDKYZZ0801) from Jishou University for talent introduction, China.

References

Enraf-Nonius (1989). CAD-4 Software. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Kiuchi, F., Chen, X. & Tsuda, Y. (1990). Heterocycles, 31, 629-36.
Li, H.-Q., Xue, J.-Y., Shi, L., Gui, S.-Y. & Zhu, H.-L. (2008). Eur. J. Med. Chem. 43, 662-667.
Niwa, K., Hashimoto, M., Morishita, S., Yokoyama, Y., Mori, H. & Tamaya, T. (1999). J. Cancer Res. 90, 726-32.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Papoutsi, Z., Kassi, E., Fokialakis, N., Mitakou, S., Lambrinidis, G., Mikros, E. & Moutsatsou, P. (2007). Steroids, 72, 693-704.
Parmar, V. S., Bisht, K. S., Jain, R., Singh, S., Sharma, S. K., Gupta, S., Malhotra, S., Tyagi, O. D., Vardhan, A. & Pati, H. N. (1996). Indian J. Chem. Sect. B, 35, 220-232.
Sanduja, R., Weinheimer, A. J. & Alam, M. (1985). J. Chem. Res. Synop. pp. 56-57.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Xiao, Z.-P., Fang, R.-Q., Shi, L., Ding, H., Xu, C. & Zhu, H.-L. (2007). Can. J. Chem. 85, 951-957.
Xiao, Z.-P., Li, H.-Q., Xue, J.-Y., Shi, L. & Zhu, H.-L. (2008). Synth. Commun. 38, 525-529.
Xiao, Z.-P., Shi, D.-H., Li, H.-Q., Zhang, L.-N., Xu, C. & Zhu, H.-L. (2007). Bioorg. Med. Chem. 15, 3703-3710.

organic compounds