Isopropyl 2,2-bis­(4-bromo­phen­yl)-2-hy­droxy­acetate

Smith, G.

doi:10.1107/S1600536812044571

Volume 68
Part 12
Page o3276
December 2012

Received 27 October 2012
Accepted 28 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.010 Å
Disorder in main residue
R = 0.055
wR = 0.156
Data-to-parameter ratio = 16.2
Details

Isopropyl 2,2-bis(4-bromophenyl)-2-hydroxyacetate

Graham Smith ^a ^*

^aScience and Engineering Faculty, Queensland University of Technology, GPO Box 2434, Brisbane, Queensland 4001, Australia
Correspondence e-mail: g.smith@qut.edu.au

The title compound, C₁₇H₁₆Br₂O₃, which is a restricted commercial acaricide (common name bromopropylate), has two independent and conformationally similar molecules in the asymmetric unit [dihedral angles between the planes of the two phenyl rings = 68.7 (4) and 77.4 (5)°]. The C atoms of the isopropyl group of one of the molecules are disordered over two sites with occupancies of 0.638 (16) and 0.362 (16). Minor non-merohedral twinning was also present in the crystal. Intermolecular O-HO hydrogen-bonding interactions involving the hydroxy groups and carboxyl O-atom acceptors give separate centrosymmetric homodimers through cyclic hydrogen-bonding motifs [graph set R₂²(10)].

Related literature

For background information on bromopropylate, see: O'Neil (2001). For the structures of benzilic acid and an analogous benzilate ester, see: Qui et al. (2007); Fu et al. (2006). For graph-set analysis, see: Etter et al. (1990).

Experimental

Crystal data

C₁₇H₁₆Br₂O₃
M_r = 428.10
Triclinic, $[P \overline 1]$
a = 10.2036 (6) Å
b = 10.2166 (6) Å
c = 17.6687 (13) Å
= 83.775 (5)°
= 73.346 (6)°
= 72.937 (5)°
V = 1686.4 (2) Å³
Z = 4
Mo K radiation
= 4.82 mm^-1
T = 200 K
0.30 × 0.20 × 0.12 mm

Data collection

Oxford Diffraction Gemini-S CCD-detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.581, T_max = 0.980
21160 measured reflections
6627 independent reflections
5435 reflections with I > 2(I)
R_int = 0.048

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.156
S = 1.08
6627 reflections
408 parameters
H-atom parameters constrained
_max = 1.20 e Å^-3
_min = -1.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O11A-H11AO22Aⁱ	0.94	1.99	2.866 (6)	154
O11C-H11CO22Cⁱⁱ	0.82	2.17	2.828 (6)	137
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y, -z.

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) within WinGX (Farrugia, 1999); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5277 ).

Acknowledgements

The author acknowledges financial support from the Australian Research Council and the Science and Engineering Faculty and the University Library, Queensland University of Technology.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies Ltd, Yarnton, England.
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Fu, D.-C., Sun, F.-X., Liu, Q. & Lv, H.-J. (2006). Acta Cryst. E62, o5284-o5285.
O'Neil, M. C. (2001). The Merck Index, 13th ed., p. 239. Whitehouse Station, NJ, USA: Merck & Co. Inc.
Qui, Y., Wang, K., Liu, Y., Deng, H., Sun, F. & Cai, Y. (2007). Inorg. Chim. Acta, 360, 1819-1824.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds