1-(5-Bromo-2-chloro­phen­yl)-2,2-di­chloro-1-(4-eth­oxy­phen­yl)cyclo­propane

Han, S.; Shi, Y.; Yuli, W.; Zhao, G.; Xu, W.

doi:10.1107/S1600536813003735

Volume 69
Part 3
Page o405
March 2013

Received 31 January 2013
Accepted 6 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 113 K
Mean (C-C) = 0.008 Å
R = 0.067
wR = 0.180
Data-to-parameter ratio = 15.4
Details

1-(5-Bromo-2-chlorophenyl)-2,2-dichloro-1-(4-ethoxyphenyl)cyclopropane

Shuwen Han,^a,^b Yongheng Shi,^a,^b Wang Yuli,^b Guilong Zhao ^b and Weiren Xu ^a,^b ^*

^aGraduate School, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, People's Republic of China, and ^bTianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
Correspondence e-mail: weiren.xu@yahoo.com

The asymmetric unit of the title compound, C₁₇H₁₄BrCl₃O, contains two independent molecules with different dihedral angles between the benzene rings [79.2 (1) and 72.7 (1)°]. In the crystal, weak C-H [pi] interactions link molecules related by translation along the b axis into two crystallographically independent chains.

Related literature

For background to sodium-glucose cotransporter 2 (SGLT2) inhibitors, see: Washburn (2009); Meng et al. (2008). For the crystal structures of related cyclopropane derivatives, see: DeLacy & Kennard (1972); Lauher & Ibers (1975).

Experimental

Crystal data

C₁₇H₁₄BrCl₃O
M_r = 420.54
Monoclinic, C 2/c
a = 27.447 (13) Å
b = 8.886 (4) Å
c = 28.861 (14) Å
= 98.348 (8)°
V = 6965 (6) Å³
Z = 16
Mo K radiation
= 2.82 mm^-1
T = 113 K
0.20 × 0.18 × 0.14 mm

Data collection

Rigaku Saturn724 CCD diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2009) T_min = 0.603, T_max = 0.694
26327 measured reflections
6143 independent reflections
4903 reflections with I > 2(I)
R_int = 0.104

Refinement

R[F² > 2(F²)] = 0.067
wR(F²) = 0.180
S = 1.09
6143 reflections
399 parameters
H-atom parameters constrained
_max = 1.54 e Å^-3
_min = -0.89 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10-C15 ring and Cg2 is the centroid of the C27-C32 ring.

D-HA	D-H	HA	DA	D-HA
C3-H3Cg1ⁱ	0.95	2.66	3.665 (3)	161
C20-H20Cg2ⁱⁱ	0.95	2.60	3.480 (9)	155
Symmetry codes: (i) x, y-1, z; (ii) x, y+1, 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: CV5386 ).

References

DeLacy, T. P. & Kennard, C. H. L. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 2141-2147.
Lauher, J. W. & Ibers, J. A. (1975). J. Am. Chem. Soc. 97, 561-567.
Meng, M., et al. (2008). J. Med. Chem. 51, 1145-1149.
Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Washburn, W. N. (2009). J. Med. Chem. 52, 1785-1794.

organic compounds