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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 [sigma](C-C) = 0.008 Å
R = 0.067
wR = 0.180
Data-to-parameter ratio = 15.4
Details
Open access

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

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[Washburn, W. N. (2009). J. Med. Chem. 52, 1785-1794.]); Meng et al. (2008[Meng, M., et al. (2008). J. Med. Chem. 51, 1145-1149.]). For the crystal structures of related cyclopropane derivatives, see: DeLacy & Kennard (1972[DeLacy, T. P. & Kennard, C. H. L. (1972). J. Chem. Soc. Perkin Trans. 2, pp. 2141-2147.]); Lauher & Ibers (1975[Lauher, J. W. & Ibers, J. A. (1975). J. Am. Chem. Soc. 97, 561-567.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14BrCl3O

  • Mr = 420.54

  • Monoclinic, C 2/c

  • a = 27.447 (13) Å

  • b = 8.886 (4) Å

  • c = 28.861 (14) Å

  • [beta] = 98.348 (8)°

  • V = 6965 (6) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 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[Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]) Tmin = 0.603, Tmax = 0.694

  • 26327 measured reflections

  • 6143 independent reflections

  • 4903 reflections with I > 2[sigma](I)

  • Rint = 0.104

Refinement
  • R[F2 > 2[sigma](F2)] = 0.067

  • wR(F2) = 0.180

  • S = 1.09

  • 6143 reflections

  • 399 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.54 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
C3-H3...Cg1i 0.95 2.66 3.665 (3) 161
C20-H20...Cg2ii 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[Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [CrossRef] [ChemPort] [ISI]
Meng, M., et al. (2008). J. Med. Chem. 51, 1145-1149.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rigaku/MSC (2009). CrystalClear-SM Expert and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Washburn, W. N. (2009). J. Med. Chem. 52, 1785-1794.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o405  [ doi:10.1107/S1600536813003735 ]

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