N-Cyclo­hexyl-3-fluoro­benzamide

Saeed, A.; Khera, R.A.; Abbas, N.; Flörke, U.

doi:10.1107/S1600536808034478

Volume 64
Part 11
Page o2209
November 2008

Received 15 October 2008
Accepted 22 October 2008
Online 25 October 2008

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
Disorder in main residue
R = 0.035
wR = 0.098
Data-to-parameter ratio = 9.9
Details

N-Cyclohexyl-3-fluorobenzamide

Aamer Saeed,^a ^* Rasheed Ahmad Khera,^a Naeem Abbas ^a and Ulrich Flörke ^b

^aDepartment of Chemistry, Quaid-I-Azam University, Islamabad 45320, Pakistan, and ^bDepartment Chemie, Fakultät für Naturwissenschaften, Universität Paderborn, Warburgerstrasse 100, D-33098 Paderborn, Germany
Correspondence e-mail: aamersaeed@yahoo.com

In the title molecule, C₁₃H₁₆FNO, the amide (N-C=O) plane is oriented at an angle of 29.9 (2)° with respect to the aromatic ring. The cyclohexane ring adopts the usual chair conformation. In the crystal structure, intermolecular N-HO hydrogen bonds link the molecules into chains along [100]. A weak C-HF interaction is also observed. The F atom is disordered over two positions with occupancy factors of 0.873 (3) and 0.127 (3).

Related literature

For related structures, see: Chopra & Guru Row (2005); Saeed et al. (2008a,b).

Experimental

Crystal data

C₁₃H₁₆FNO
M_r = 221.27
Monoclinic, P 2₁
a = 5.267 (3) Å
b = 6.599 (4) Å
c = 16.755 (9) Å
= 90.090 (17)°
V = 582.4 (6) Å³
Z = 2
Mo K radiation
= 0.09 mm^-1
T = 120 (2) K
0.45 × 0.40 × 0.21 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.962, T_max = 0.978
5071 measured reflections
1492 independent reflections
1420 reflections with I > 2(I)
R_int = 0.034

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.098
S = 1.05
1492 reflections
150 parameters
1 restraint
H-atom parameters constrained
_max = 0.25 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	0.88	2.25	3.050 (2)	152
C5-H5AF1ⁱⁱ	0.95	2.58	3.310 (3)	134
Symmetry codes: (i) x+1, y, z; (ii) $[-x+2, y+{\script{1\over 2}}, -z+1]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: CI2689 ).

Acknowledgements

NA is grateful to the Higher Education Commission of Pakistan for financial support for a PhD programme.

References

Bruker (2002). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chopra, D. & Guru Row, T. N. (2005). Cryst. Growth Des. 5, 1679-1681.
Saeed, A., Abbas, N., Hussain, S. & Flörke, U. (2008a). Acta Cryst. E64, o773.
Saeed, A., Khera, R. A., Batool, M., Shaheen, U. & Flörke, U. (2008b). Acta Cryst. E64, o1625.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds