2-[Anilino(phen­yl)meth­yl]cyclo­heptan­one

Eftekhari-Sis, B.; Mohajer, S.; Zirak, M.; Mozaffarnia, S.; Büyükgüngör, O.

doi:10.1107/S1600536812050659

Volume 69
Part 1
Page o109
January 2013

Received 18 August 2012
Accepted 12 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.136
Data-to-parameter ratio = 17.0
Details

2-[Anilino(phenyl)methyl]cycloheptanone

Bagher Eftekhari-Sis,^a ^* Sahar Mohajer,^a Maryam Zirak,^b Sakineh Mozaffarnia ^a and Orhan Büyükgüngör ^c

^aDepartment of Chemistry, University of Maragheh, Maragheh, Iran,^bDepartment of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran, and ^cDepartment of Physics, Ondokuz Mayis University, TR-55139, Samsun, Turkey
Correspondence e-mail: eftekharisis@maragheh.ac.ir

In the title compound, C₂₀H₂₃NO, the cycloheptanone ring adopts a twist-chair conformation, with the aminomethyl substituent in an equatorial position. The relative configuration of the two stereocenters is R,R. In the crystal, molecules are linked by N-HO hydrogen bonds into chains along [100].

Related literature

For the synthesis of title compound and related compounds, see: Eftekhari-Sis et al. (2013). For the biological activity of -amino ketones, see: Arend et al. (1998); Jadhav et al. (2008); Kalluraya et al. (2001). For information on the Mannich reaction, see, for example: Eftekhari-Sis et al. (2006); Azizi et al. (2006); Cordova (2004). For the crystal structures of related compounds, see: Eftekhari-Sis et al. (2012); Yuan et al. (2007); Fun et al. (2009). For puckering parameters, see: Evans & Boeyens (1989).

Experimental

Crystal data

C₂₀H₂₃NO
M_r = 293.39
Monoclinic, P 2₁ /c
a = 5.7534 (4) Å
b = 16.1336 (8) Å
c = 18.1980 (13) Å
= 99.371 (6)°
V = 1666.65 (19) Å³
Z = 4
Mo K radiation
= 0.07 mm^-1
T = 296 K
0.72 × 0.56 × 0.27 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.965, T_max = 0.985
10757 measured reflections
3449 independent reflections
2170 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.136
S = 1.01
3449 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.26 e Å^-3
_min = -0.13 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	0.879 (19)	2.23 (2)	3.065 (2)	158.4 (16)
Symmetry code: (i) x+1, y, z.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2069 ).

Acknowledgements

The research council of the University of Maragheh is acknowledged for financial support.

References

Arend, M., Westermann, B. & Risch, N. (1998). Angew. Chem. Int. Ed. 37, 1044-1070.
Azizi, N., Torkiyan, L. & Saidi, M. R. (2006). Org. Lett. 8, 2079-2082.
Cordova, A. (2004). Acc. Chem. Res. 37, 102-112.
Eftekhari-Sis, B., Abdollahifar, A., Hashemi, M. M. & Zirak, M. (2006). Eur. J. Org. Chem. pp. 5152-5157.
Eftekhari-Sis, B., Mohajer, S. & Büyükgüngör, O. (2012). Acta Cryst. E68, o2829.
Eftekhari-Sis, B., Mohajer, S., Mahdavinia, G. R. & Büyükgüngör, O. (2013). RSC Advances. Submitted.
Evans, D. G. & Boeyens, J. C. A. (1989). Acta Cryst. B45, 581-590.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Fun, H.-K., Chantrapromma, S., Rai, S., Shetty, P. & Isloor, A. M. (2009). Acta Cryst. E65, o539-o540.
Jadhav, V. J., Kulkarni, M. V., Rasal, V. P., Biradar, S. S. & Vinay, M. D. (2008). Eur. J. Med. Chem. 43, 1721-1729.
Kalluraya, B., Isloor, A. M., Chimbalkar, R. & Shenoy, S. (2001). Indian J. Heterocycl. Chem. pp. 239-240.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.
Yuan, G.-X., Sun, J.-B., Zhang, L.-H. & Lu, G. (2007). Acta Cryst. E63, o3960.

organic compounds