5-Bromo-2-hy­droxy­benzonitrile

Oh, S.; Tanski, J.M.

doi:10.1107/S1600536812031716

Volume 68
Part 9
Page o2617
September 2012

Received 5 July 2012
Accepted 11 July 2012
Online 1 August 2012

Key indicators
Single-crystal X-ray study
T = 125 K
Mean (C-C) = 0.005 Å
R = 0.043
wR = 0.100
Data-to-parameter ratio = 22.5
Details

5-Bromo-2-hydroxybenzonitrile

Scott Oh ^a and Joseph M. Tanski ^a ^*

^aDepartment of Chemistry, Vassar College, Poughkeepsie, NY 12604, USA
Correspondence e-mail: jotanski@vassar.edu

The title compound, C₇H₄BrNO, crystallizes with two molecules in the asymmetric unit. The two molecules exhibit nearly linear C-C [triple bond] N nitrile bond angles of 179.1 (4) and 177.1 (4)°. In the crystal, the molecules are linked into a one-dimensional hydrogen-bonded chain by interactions between the phenol H atom and the nitrile N atom [NO = 2.805 (4) and 2.810 (4) Å].

Related literature

For information on the synthesis of the title compound, see: Anwar & Hansen (2008); Bonnichon et al. (1999); Oberhauser (1997); Tamilselvan et al. (2009). For use as a synthetic reagent, see: Jiang et al. (2011); Tsuhako et al. (2012); Wetzel et al. (2011). For a related crystal structure, see: Beswick et al. (1996).

Experimental

Crystal data

C₇H₄BrNO
M_r = 198.01
Triclinic, $[P \overline 1]$
a = 3.8422 (3) Å
b = 8.5166 (7) Å
c = 21.6507 (18) Å
= 97.074 (1)°
= 91.991 (1)°
= 97.068 (1)°
V = 696.83 (10) Å³
Z = 4
Mo K radiation
= 5.82 mm^-1
T = 125 K
0.20 × 0.07 × 0.03 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.389, T_max = 0.845
11040 measured reflections
4213 independent reflections
3254 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.100
S = 1.03
4213 reflections
187 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 1.67 e Å^-3
_min = -0.57 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1N2	0.83 (2)	1.98 (2)	2.805 (4)	170 (5)
O2-H2N1ⁱ	0.84 (2)	1.98 (2)	2.810 (4)	175 (5)
Symmetry code: (i) x-1, y+1, z.

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; 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: RK2372 ).

Acknowledgements

This work was supported by Vassar College. X-ray facilities were provided by the US National Science Foundation (grant No. 0521237 to JMT).

References

Anwar, H. F. & Hansen, T. V. (2008). Tetrahedron Lett. 49, 4443-4445.
Beswick, C., Kubicki, M. & Codding, P. W. (1996). Acta Cryst. C52, 3171-3173.
Bonnichon, F., Grabner, G., Guyot, G. & Richard, C. (1999). J. Chem. Soc. Perkin Trans. 2, pp. 1203-1210.
Bruker (2007). SAINT, SADABS and APEX2. Bruxer AXS Inc., Madison, Wisconsin, USA.
Jiang, S., Tala, S. R., Lu, H., Abo-Dya, N. E., Avan, I., Gyanda, K., Lu, L., Katritzky, A. R. & Debnath, A. K. (2011). J. Med. Chem. 54, 572-579.
Oberhauser, T. (1997). J. Org. Chem. 62, 4504-4506.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tamilselvan, P., Basavaraju, Y. B., Sampathkumar, E. & Murugesan, R. (2009). Catal. Commun. 10, 716-719.
Tsuhako, A. L., et al. (2012). Bioorg. Med. Chem. Lett. 22, 3732-3738.
Wetzel, M., Marchais-Oberwinkler, S., Perspicace, E., Möller, G., Adamski, J. & Hartmann, R. W. (2011). J. Med. Chem. 54, 7547-7557.

organic compounds