1-(2-Bromophenyl)ethane-1,2-diyl 1,1′-biphenyl-2,2′-dicarboxylate

Fun, H.-K.; Quah, C.K.; Wu, D.

doi:10.1107/S1600536812018053

Volume 68
Part 5
Page o1552
May 2012

Received 20 April 2012
Accepted 23 April 2012
Online 28 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.004 Å
R = 0.039
wR = 0.102
Data-to-parameter ratio = 22.0
Details

1-(2-Bromophenyl)ethane-1,2-diyl 1,1'-biphenyl-2,2'-dicarboxylate

Hoong-Kun Fun,^a ^*⁺ Ching Kheng Quah ^a ⁺⁺ and Dongdong Wu ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing, 210093, People's Republic of China
Correspondence e-mail: hkfun@usm.my

In the title compound, C₂₂H₁₅BrO₄, the bromobenzene ring is inclined at dihedral angles of 23.87 (11) and 52.37 (11)° with respect to the planes of the two benzene rings. The two benzene rings of the biphenyl unit form a dihedral angle of 49.08 (11)°. In the crystal, molecules are linked into [100] chains by C-HO hydrogen bonds.

Related literature

For a related structure, references to other similar structures and chemical and biological background, see: Fun et al. (2012). For the preparation, see: Wu et al. (2012).

Experimental

Crystal data

C₂₂H₁₅BrO₄
M_r = 423.25
Monoclinic, P 2₁ /c
a = 8.0436 (9) Å
b = 21.775 (2) Å
c = 12.8809 (11) Å
= 125.613 (5)°
V = 1834.1 (3) Å³
Z = 4
Mo K radiation
= 2.27 mm^-1
T = 296 K
0.41 × 0.23 × 0.17 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.456, T_max = 0.702
17934 measured reflections
5372 independent reflections
3377 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.102
S = 1.02
5372 reflections
244 parameters
H-atom parameters constrained
_max = 0.50 e Å^-3
_min = -0.64 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C21-H21AO1ⁱ	0.93	2.44	3.321 (3)	158
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6749 ).

Acknowledgements

HKF and CKQ thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160). Financial support from the National Natural Science Foundation of China (20972067) is acknowledged.

References

Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Fun, H.-K., Quah, C. K. & Wu, D. (2012). Acta Cryst. E68, accepted [IS5123].
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wu, D., Wang, L., Xu, K., Song, J., Fun, H-K., Xu, J. & Zhang, Y. (2012). Chem. Commun. 48, 1168-1170.

organic compounds