3-(4-Chloro­phen­yl)-5-phenyl-4,5-di­hydro-1,3-oxazole

Islor, A.M.; Yaradoni, R.; Garudachari, B.; Gerber, T.; Hosten, E.; Betz, R.

doi:10.1107/S1600536812043711

Volume 68
Part 11
Page o3215
November 2012

Received 9 October 2012
Accepted 22 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 200 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.103
Data-to-parameter ratio = 19.2
Details

3-(4-Chlorophenyl)-5-phenyl-4,5-dihydro-1,3-oxazole

Arun M. Islor,^a Rajiv Yaradoni,^a B. Garudachari,^a Thomas Gerber,^b Eric Hosten ^b and Richard Betz ^b ^*

^aNational Institute of Technology-Karnataka, Department of Chemistry, Medicinal Chemistry Laboratory, Surathkal, Mangalore 575 025, India, and ^bNelson Mandela Metropolitan University, Summerstrand Campus, Department of Chemistry, University Way, Summerstrand, PO Box 77000, Port Elizabeth, 6031, South Africa
Correspondence e-mail: richard.betz@webmail.co.za

In the title compound, C₁₅H₁₂ClNO, the isoxazoline ring adopts an envelope conformation with the C atom bearing an unsubstituted phenyl ring as the flap atom. The chlorinated phenyl group is nearly in-plane with the four coplanar atoms of the heterocycle and the corresponding mean planes enclosing an angle of 1.16 (7)°. The unsubstituted phenyl group attached to the envelope flap atom approaches a nearly perpendicular orientation relative to the isoxazoline ring with a dihedral angle of 74.93 (7)°. In the crystal, weak C-HO, C-HN and C-H [pi] interactions connect the molecules into layers perpendicular to the a axis.

Related literature

For the biological and medicinal importance of isoxazole compounds, see: Miller et al. (2009); Prasad et al. (2007). For their use in ring-opening polymerizations, see: Wiesbrock et al. (2005). For the puckering analysis of five-membered rings, see: Cremer & Pople (1975). For graph-set analysis of hydrogen bonds, see: Etter et al. (1990); Bernstein et al. (1995).

Experimental

Crystal data

C₁₅H₁₂ClNO
M_r = 257.71
Monoclinic, C 2/c
a = 29.797 (5) Å
b = 10.717 (5) Å
c = 8.086 (5) Å
= 103.088 (5)°
V = 2515 (2) Å³
Z = 8
Mo K radiation
= 0.29 mm^-1
T = 200 K
0.58 × 0.42 × 0.21 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.850, T_max = 0.943
11843 measured reflections
3132 independent reflections
2637 reflections with I > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.103
S = 1.03
3132 reflections
163 parameters
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11-C16 ring.

D-HA	D-H	HA	DA	D-HA
C12-H12N1ⁱ	0.95	2.74	3.657 (2)	163
C12-H12O1ⁱ	0.95	2.65	3.390 (2)	135
C2-H2BO1ⁱⁱ	0.99	2.67	3.466 (2)	138
C26-H26O1ⁱⁱ	0.95	2.70	3.431 (2)	134
C22-H22Cgⁱⁱⁱ	0.95	2.81	3.721 (3)	162
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2526 ).

Acknowledgements

AMI is thankful to the Department of Atomic Energy, Board for Research in Nuclear Sciences, Government of India, for the Young Scientist award.

References

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Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256-262.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Miller, J. J., Rajaram, S., Pfaffenroth, C. & Sigman, M. S. (2009). Tetrahedron, 65, 3110-3119.
Prasad, Y. R., Kumar, P. R. & Ramesh, B. (2007). Int. J. Chem. Sci. 5, 542-548.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Wiesbrock, F., Hoogenboom, R., Leenen, M. A. M., Meier, M. A. R. & Schubert, U. S. (2005). Macromolecules, 38, 5025-5034.

organic compounds