(4-Meth­oxy­phen­yl)(4-propyl­cyclo­hex­yl)methanone

Wang, L.; Chang, Z.-Q.; Zhang, J.; Li, C.-M.

doi:10.1107/S1600536813003644

Volume 69
Part 3
Page o404
March 2013

Received 30 January 2013
Accepted 5 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.002 Å
R = 0.045
wR = 0.129
Data-to-parameter ratio = 19.5
Details

(4-Methoxyphenyl)(4-propylcyclohexyl)methanone

Ling Wang,^a Zi-Qian Chang,^a Jie Zhang ^a and Cheng-Min Li ^a ^*

^aPharmacy Department of the Second Artillery General Hospital, Beijing 100088, People's Republic of China
Correspondence e-mail: chengmin_li@yahoo.com

The asymmetric unit of the title compound, C₁₇H₂₄O₂, contains two independent molecules with different conformations. The least-squares plane through the cyclohexane ring makes dihedral angles of 52.9 (5) and 81.4 (4)° with the benzene ring in the two molecules. The cyclohexane ring adopts a chair conformation in both molecules. In the crystal, weak C-HO hydrogen bonds link molecules related by translation in [100] into two crystallographically independent chains.

Related literature

For the antihyperglycemic activity of SGLT2 inhibitors, see: Washburn (2009); Zhao et al. (2011); Shao et al. (2011). For the structure of (5-bromo-2-methoxyphenyl)(4-ethylcyclohexyl)methanone, see: Wang et al. (2011).

Experimental

Crystal data

C₁₇H₂₄O₂
M_r = 260.36
Triclinic, $[P \overline 1]$
a = 5.679 (1) Å
b = 7.3260 (12) Å
c = 35.020 (4) Å
= 93.74 (1)°
= 91.877 (6)°
= 94.436 (1)°
V = 1448.5 (4) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 113 K
0.18 × 0.16 × 0.14 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009) T_min = 0.986, T_max = 0.989
14496 measured reflections
6762 independent reflections
5234 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.129
S = 1.03
6762 reflections
347 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9O1ⁱ	1.00	2.58	3.4661 (14)	147
C26-H26O3ⁱⁱ	1.00	2.58	3.5200 (14)	156
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z.

Data collection: CrystalClear (Rigaku/MSC, 2009); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CV5385 ).

References

Rigaku/MSC (2009). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Shao, H., Gao, Y. L., Lou, Y. Y., Wang, Y. L., Liu, W., Xu, W. R., Wang, J. W., Zhao, G. L. & Tang, L. D. (2011). Chin. J. Org. Chem. 31, 836-842.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, L., Chang, Z., Ding, C., Shao, H. & Sun, J. (2011). Acta Cryst. E67, o1173.
Washburn, W. N. (2009). J. Med. Chem. 52, 1785-1794.
Zhao, W. J., Shi, Y. H., Zhao, G. L., Wang, Y. L., Shao, H., Tang, L. D. & Wang, J. W. (2011). Chin. Chem. Lett. 22, 1215-1218.

organic compounds