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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 [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.136
Data-to-parameter ratio = 17.0
Details
Open access

2-[Anilino(phenyl)methyl]cycloheptanone

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-H...O hydrogen bonds into chains along [100].

Related literature

For the synthesis of title compound and related compounds, see: Eftekhari-Sis et al. (2013[Eftekhari-Sis, B., Mohajer, S., Mahdavinia, G. R. & Büyükgüngör, O. (2013). RSC Advances. Submitted.]). For the biological activity of [beta]-amino ketones, see: Arend et al. (1998[Arend, M., Westermann, B. & Risch, N. (1998). Angew. Chem. Int. Ed. 37, 1044-1070.]); Jadhav et al. (2008[Jadhav, V. J., Kulkarni, M. V., Rasal, V. P., Biradar, S. S. & Vinay, M. D. (2008). Eur. J. Med. Chem. 43, 1721-1729.]); Kalluraya et al. (2001[Kalluraya, B., Isloor, A. M., Chimbalkar, R. & Shenoy, S. (2001). Indian J. Heterocycl. Chem. pp. 239-240.]). For information on the Mannich reaction, see, for example: Eftekhari-Sis et al. (2006[Eftekhari-Sis, B., Abdollahifar, A., Hashemi, M. M. & Zirak, M. (2006). Eur. J. Org. Chem. pp. 5152-5157.]); Azizi et al. (2006[Azizi, N., Torkiyan, L. & Saidi, M. R. (2006). Org. Lett. 8, 2079-2082.]); Cordova (2004[Cordova, A. (2004). Acc. Chem. Res. 37, 102-112.]). For the crystal structures of related compounds, see: Eftekhari-Sis et al. (2012[Eftekhari-Sis, B., Mohajer, S. & Büyükgüngör, O. (2012). Acta Cryst. E68, o2829.]); Yuan et al. (2007[Yuan, G.-X., Sun, J.-B., Zhang, L.-H. & Lu, G. (2007). Acta Cryst. E63, o3960.]); Fun et al. (2009[Fun, H.-K., Chantrapromma, S., Rai, S., Shetty, P. & Isloor, A. M. (2009). Acta Cryst. E65, o539-o540.]). For puckering parameters, see: Evans & Boeyens (1989[Evans, D. G. & Boeyens, J. C. A. (1989). Acta Cryst. B45, 581-590.]).

[Scheme 1]

Experimental

Crystal data
  • C20H23NO

  • Mr = 293.39

  • Monoclinic, P 21 /c

  • a = 5.7534 (4) Å

  • b = 16.1336 (8) Å

  • c = 18.1980 (13) Å

  • [beta] = 99.371 (6)°

  • V = 1666.65 (19) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Stoe & Cie (2002). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.965, Tmax = 0.985

  • 10757 measured reflections

  • 3449 independent reflections

  • 2170 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 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[Stoe & Cie (2002). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008)[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


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.  [ISI] [CrossRef]
Azizi, N., Torkiyan, L. & Saidi, M. R. (2006). Org. Lett. 8, 2079-2082.  [ISI] [CrossRef] [PubMed] [ChemPort]
Cordova, A. (2004). Acc. Chem. Res. 37, 102-112.  [ISI] [PubMed] [ChemPort]
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.  [CSD] [CrossRef] [details]
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.  [CrossRef] [ISI] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fun, H.-K., Chantrapromma, S., Rai, S., Shetty, P. & Isloor, A. M. (2009). Acta Cryst. E65, o539-o540.  [CSD] [CrossRef] [details]
Jadhav, V. J., Kulkarni, M. V., Rasal, V. P., Biradar, S. S. & Vinay, M. D. (2008). Eur. J. Med. Chem. 43, 1721-1729.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
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.  [CrossRef] [details]
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.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o109  [ doi:10.1107/S1600536812050659 ]

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