(IUCr) 2-Bromobenzaldehyde cyanohydrin

Volume 64
Part 1
Page o55
January 2008

Received 3 October 2007
Accepted 9 October 2007
Online 6 December 2007

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.004 Å
R = 0.032
wR = 0.083
Data-to-parameter ratio = 18.1
Details

2-Bromobenzaldehyde cyanohydrin

Richard Betz,^a Franziska Betzler ^a and Peter Klüfers ^a ^*

^aLudwig-Maximilians-Universität, Department Chemie und Biochemie, Butenandtstrasse 5-13, 81377 München, Germany
Correspondence e-mail: kluef@cup.uni-muenchen.de

The title compound [alternatively called (2-bromophenyl)(hydroxy)acetonitrile], C₈H₆BrNO, is the reaction product of 2-bromobenzaldehyde and hydrogen cyanide. Bond lengths and angles are normal. In the crystal structure, an intermolecular hydrogen bond between the hydroxy group and the nitrile N atom is established. In agreement with bonding considerations, a linear C-NH acceptor geometry is observed. Each molecule is a single donor and a single acceptor; extended hydrogen-bonded chains are formed along [100].

Related literature

For the synthesis of the title compound, see: Becker et al. (2001). For the crystal structure of a related compound, see: Flores-Morales et al. (2003). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₈H₆BrNO
M_r = 212.05
Orthorhombic, P b c a
a = 8.0538 (3) Å
b = 13.9970 (5) Å
c = 14.2969 (5) Å
V = 1611.68 (10) Å³
Z = 8
Mo K radiation
= 5.04 mm^-1
T = 200 (2) K
0.14 × 0.09 × 0.03 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001) T_min = 0.624, T_max = 0.86
19593 measured reflections
1844 independent reflections
1351 reflections with I > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.083
S = 1.02
1844 reflections
102 parameters
Only H-atom displacement parameters refined
_max = 0.29 e Å^-3
_min = -0.59 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O-H82Nⁱ	0.84	2.01	2.844 (3)	170
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH2526 ).

Acknowledgements

The authors thank Dr Peter Mayer and Sandra Albrecht for professional support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Becker, H. G. O., Beckert, R., Domschke, G., Fanghänel, E., Habicher, W. D., Metz, P., Pavel, D. & Schwetlick, K. (2001). Organikum - Organisch-chemisches Grundpraktikum. Weinheim: Wiley-VCH.
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Flores-Morales, V., Fernández-Zertuche, M. & Ordóñez, M. (2003). Tetrahedron Asymmetry, 14, 2693-2698.
Nonius (2004). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Sheldrick, G. M. (2001). SADABS. Version 2. University of Göttingen, Germany.

organic compounds