(5-Bromo-2-hydroxy­phen­yl)(phen­yl)methanone

Zheng, C.-Z.; Ji, C.-Y.; Chang, X.-L.; Zhang, L.-Q.

doi:10.1107/S160053680803969X

Volume 64
Part 12
Page o2486
December 2008

Received 22 November 2008
Accepted 25 November 2008
Online 29 November 2008

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.004 Å
R = 0.029
wR = 0.073
Data-to-parameter ratio = 13.2
Details

(5-Bromo-2-hydroxyphenyl)(phenyl)methanone

Chang-Zheng Zheng,^a Chang-You Ji,^a ^* Xiu-Li Chang ^b and Li-Qin Zhang ^a

^aCollege of Environmental and Chemical Engineering, Xi'an Polytechnic University, 710048 Xi'an, Shaanxi, People's Republic of China, and ^bDepartment of Materials Science and Chemical Engineering, Sichuan University of Science and Engineering , 643000 Zigong, Sichuan, People's Republic of China
Correspondence e-mail: jichangyou789456@126.com

In the title compound, C₁₃H₉BrO₂, the dihedral angle between the aromatic ring planes is 53.6 (1)°. The crystal structure is stabilized by intramolecular O-HO and intermolecular C-HO hydrogen bonding and C-H [pi] interactions.

Related literature

For the ability of aroylhydrazones to coordinate to metal ions and their biological activity, see: Singh et al. (1982); Salem (1998); Carcelli et al. (1995).

Experimental

Crystal data

C₁₃H₉BrO₂
M_r = 277.11
Monoclinic, P 2₁ /c
a = 15.9510 (18) Å
b = 5.8956 (6) Å
c = 12.1260 (14) Å
= 106.166 (2)°
V = 1095.2 (2) Å³
Z = 4
Mo K radiation
= 3.73 mm^-1
T = 298 K
0.15 × 0.10 × 0.06 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.604, T_max = 0.807
5479 measured reflections
1933 independent reflections
1578 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.072
S = 1.03
1933 reflections
146 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.52 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2	0.82	1.85	2.569 (3)	146
C3-H3O1ⁱ	0.93	2.60	3.488 (3)	160
C12-H12Cg1ⁱⁱ	0.93	2.93	3.596 (3)	130
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ . Cg1 is the centroid of the C8-C13 ring.

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); 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 (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2684 ).

Acknowledgements

This project was supported by the Postgraduate Foundation of Xi'an Polytechnic University (No. Y05-2-09)

References

Carcelli, M., Mazza, P., Pelizzi, G. & Zani, F. (1995). J. Inorg. Biochem. 57, 43-62.
Salem, A. A. (1998). Microchem. J. 60, 51-66.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Singh, R. B., Jain, P. & Singh, R. P. (1982). Talanta, 29, 77-84.

organic compounds