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Volume 68 
Part 12 
Page o3282  
December 2012  

Received 19 September 2012
Accepted 30 October 2012
Online 3 November 2012

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.051
wR = 0.150
Data-to-parameter ratio = 19.3
Details
Open access

2,4-Bis(2-ethoxyphenyl)-3-azabicyclo[3.3.1]nonan-9-one

aDepartment of Biomedicinal Chemistry, Inje University, Gimhae, Gyeongnam 621 749, Republic of Korea, and bDepartment of Chemistry, IIT Madras, Chennai 600 036, TamilNadu, India
Correspondence e-mail: parthisivam@yahoo.co.in

The asymmetric unit of the title compound, C24H29NO3, contains two independent molecules, which each exibit a twin-chair conformation with an equatorial orientation of the ortho-ethoxyphenyl groups but different dihedral angles [41.3 (1) and 24.1 (1)°] between the benzene rings. In the crystal, pairs of weak C-H...O hydrogen bonds link the two different independent molecules into dimers.

Related literature

For the synthesis and stereochemistry of 3-azabicyclo[3.3.1]nonan-9-ones, see: Park et al. (2011[Park, D. H., Jeong, Y. T. & Parthiban, P. (2011). J. Mol. Struct. 1005, 31-44.]) and for their biological properties, see: Jeyaraman & Avila (1981[Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.]); Park et al. (2012a[Park, D. H., Venkatesn, J., Kim, S. K. & Prthiban, P. (2012a). Bioorg. Med. Chem. Lett. 22, 6004-6009.]); Parthiban et al. (2010a[Parthiban, P., Rathika, P., Ramkumar, V., Son, S. M. & Jeong, Y. T. (2010a). Bioorg. Med. Chem. Lett. 20, 1642-1647.],b[Parthiban, P., Rathika, P., Park, K. S. & Jeong, Y. T. (2010b). Monatsh. Chem. 141, 79-93.]; 2011a[Parthiban, P., Subalakshmi, V., Balasubramanian, K., Islam, Md. N., Choi, J. S. & Jeong, Y. T. (2011a). Bioorg. Med. Chem. Lett. 21, 2287-2296.]). For similar structures, see: Park et al. (2012b[Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o2841.]); Parthiban et al. (2009a[Parthiban, P., Ramkumar, V., Kim, M. S., Son, S. M. & Jeong, Y. T. (2009a). Acta Cryst. E65, o1383.],b[Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2009b). Acta Cryst. E65, o3103.]; 2011b[Parthiban, P., Ramkumar, V., Park, D. H. & Jeong, Y. T. (2011b). Acta Cryst. E67, o1475-o1476.]). For conformational analysis, see: Kalsi (1997[Kalsi, P. S. (1997). In Stereochemistry: Conformation and Mechanism. New Delhi: New Age International (P) Ltd.]); Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C24H29NO3

  • Mr = 379.49

  • Triclinic, [P \overline 1]

  • a = 9.7981 (3) Å

  • b = 13.6139 (5) Å

  • c = 16.7098 (6) Å

  • [alpha] = 74.363 (2)°

  • [beta] = 80.464 (2)°

  • [gamma] = 83.563 (2)°

  • V = 2111.42 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 298 K

  • 0.35 × 0.28 × 0.22 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.983

  • 27579 measured reflections

  • 9839 independent reflections

  • 6037 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.150

  • S = 1.02

  • 9839 reflections

  • 509 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.53 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C23-H23A...O1A 0.97 2.42 3.311 (3) 153
C23A-H23C...O1 0.97 2.43 3.297 (3) 149

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5345 ).


Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the X-ray data collection.

References

Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.  [CrossRef] [ChemPort] [ISI]
Kalsi, P. S. (1997). In Stereochemistry: Conformation and Mechanism. New Delhi: New Age International (P) Ltd.
Park, D. H., Jeong, Y. T. & Parthiban, P. (2011). J. Mol. Struct. 1005, 31-44.  [ISI] [CrossRef] [ChemPort]
Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o2841.  [CSD] [CrossRef] [details]
Park, D. H., Venkatesn, J., Kim, S. K. & Prthiban, P. (2012a). Bioorg. Med. Chem. Lett. 22, 6004-6009.  [CSD] [CrossRef] [ChemPort] [PubMed]
Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2009b). Acta Cryst. E65, o3103.  [CSD] [CrossRef] [details]
Parthiban, P., Ramkumar, V., Kim, M. S., Son, S. M. & Jeong, Y. T. (2009a). Acta Cryst. E65, o1383.  [CSD] [CrossRef] [details]
Parthiban, P., Ramkumar, V., Park, D. H. & Jeong, Y. T. (2011b). Acta Cryst. E67, o1475-o1476.  [CSD] [CrossRef] [ChemPort] [details]
Parthiban, P., Rathika, P., Park, K. S. & Jeong, Y. T. (2010b). Monatsh. Chem. 141, 79-93.  [CrossRef] [ChemPort]
Parthiban, P., Rathika, P., Ramkumar, V., Son, S. M. & Jeong, Y. T. (2010a). Bioorg. Med. Chem. Lett. 20, 1642-1647.  [CSD] [CrossRef] [ChemPort] [PubMed]
Parthiban, P., Subalakshmi, V., Balasubramanian, K., Islam, Md. N., Choi, J. S. & Jeong, Y. T. (2011a). Bioorg. Med. Chem. Lett. 21, 2287-2296.  [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3282  [ doi:10.1107/S1600536812044856 ]

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