1-(4-Chloro­phen­yl)-3-(2-meth­oxy­anilino)propan-1-one

Llovera, L.; Anzenbacher, P.; López, S.E.; González, T.

doi:10.1107/S1600536810054449

Volume 67
Part 2
Page o315
February 2011

Received 16 December 2010
Accepted 27 December 2010
Online 12 January 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.077
wR = 0.198
Data-to-parameter ratio = 16.7
Details

1-(4-Chlorophenyl)-3-(2-methoxyanilino)propan-1-one

Ligia Llovera,^a Pavel Anzenbacher Jr,^b Simón E. López ^a and Teresa González ^c ^*

^aLaboratorio 223, Departamento de Química, Universidad Simon Bolivar (USB), Apartado 47206, Caracas 1080-A, Venezuela,^bDepartment of Chemistry, Center for Photochemical Sciences, Bowling Green State University (BGSU), Bowling Green, OH 43-403, USA, and ^cCentro de Química, Instituto Venezolano de Investigaciones Científicas, Apartado 21827, Caracas 1020-A, Venezuela
Correspondence e-mail: tegonzal@ivic.gob.ve, tegonzal1969@gmail.com

In the title compound, C₁₆H₁₆ClNO₂, the molecule adopts a bowed conformation, with a dihedral angle of 39.9 (2)° between the aromatic rings. In the crystal, molecules are linked by C-HO hydrogen bonds, generating C(6) chains propagating in [010]. Very weak aromatic [pi] - [pi] stacking is also observed [centroid-centroid distance = 4.040 (2) Å].

Related literature

For the synthesis of quinoline derivatives, see: Peifer et al. (2007). For background to the antimicrobial activity of quinolines, see: Yamashkin & Oreshkina (2006). For further synthetic details, see: Dienys et al. (1977); Volkov et al. (2007).

Experimental

Crystal data

C₁₆H₁₆ClNO₂
M_r = 289.75
Orthorhombic, P b c a
a = 7.1690 (6) Å
b = 14.4303 (11) Å
c = 28.667 (3) Å
V = 2965.6 (4) Å³
Z = 8
Mo K radiation
= 0.26 mm^-1
T = 293 K
0.48 × 0.36 × 0.20 mm

Data collection

Rigaku AFC-7S Mercury diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998) T_min = 0.927, T_max = 0.950
31012 measured reflections
3035 independent reflections
2016 reflections with I > 2(I)
R_int = 0.057

Refinement

R[F² > 2(F²)] = 0.077
wR(F²) = 0.198
S = 1.14
3035 reflections
182 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C15-H15AO2ⁱ	0.93	2.49	3.414 (4)	171
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: CrystalStructure (Rigaku/MSC, 2005) and SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1999); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5773 ).

Acknowledgements

The authors thank the Decanato de Investigación y Desarrollo (DID-USB, Caracas) and the FONACIT-MCT (project LAB-97000821) for financial support. LL thanks the Decanato de Estudios de Postgrado (USB, Caracas) for a travel-training fellowship.

References

Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Dienys, G., Gureviciene, J., Cekuoliene, L. & Steponavicius, J. (1977). Lietuvus TSR Mokslu akademijos darbai Ser. B, 1, 33-38.
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan
Peifer, C., Kinkel, K., Abadleh, M., Schollmeyer, D. & Laufer, S. (2007). J. Med. Chem. 50, 1213-1221.
Rigaku/MSC (2005). CrystalClear and CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Volkov, S. V., Kutyakov, S. V., Levov, A. N., Polyakova, E. I., Anh, L. T., Soldatova, S. A., Terentiev, P. B. & Soldatenkov, A. T. (2007). Chem. Heterocycl. Compd, 43, 445-453.
Yamashkin, S. A. & Oreshkina, E. A. (2006). Chem. Heterocycl. Compd, 42, 701-718.

organic compounds