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

Park, D.H.; Ramkumar, V.; Parthiban, P.

doi:10.1107/S1600536812044856

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 (C-C) = 0.003 Å
R = 0.051
wR = 0.150
Data-to-parameter ratio = 19.3
Details

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

Dong Ho Park,^a V. Ramkumar ^b and P. Parthiban ^a ^*

^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-HO 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) and for their biological properties, see: Jeyaraman & Avila (1981); Park et al. (2012a); Parthiban et al. (2010a,b; 2011a). For similar structures, see: Park et al. (2012b); Parthiban et al. (2009a,b; 2011b). For conformational analysis, see: Kalsi (1997); Cremer & Pople (1975).

Experimental

Crystal data

C₂₄H₂₉NO₃
M_r = 379.49
Triclinic, $[P \overline 1]$
a = 9.7981 (3) Å
b = 13.6139 (5) Å
c = 16.7098 (6) Å
= 74.363 (2)°
= 80.464 (2)°
= 83.563 (2)°
V = 2111.42 (13) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.973, T_max = 0.983
27579 measured reflections
9839 independent reflections
6037 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.150
S = 1.02
9839 reflections
509 parameters
H-atom parameters constrained
_max = 0.53 e Å^-3
_min = -0.45 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C23-H23AO1A	0.97	2.42	3.311 (3)	153
C23A-H23CO1	0.97	2.43	3.297 (3)	149

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); 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); 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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.
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.
Park, D. H., Ramkumar, V. & Parthiban, P. (2012b). Acta Cryst. E68, o2841.
Park, D. H., Venkatesn, J., Kim, S. K. & Prthiban, P. (2012a). Bioorg. Med. Chem. Lett. 22, 6004-6009.
Parthiban, P., Ramkumar, V. & Jeong, Y. T. (2009b). Acta Cryst. E65, o3103.
Parthiban, P., Ramkumar, V., Kim, M. S., Son, S. M. & Jeong, Y. T. (2009a). Acta Cryst. E65, o1383.
Parthiban, P., Ramkumar, V., Park, D. H. & Jeong, Y. T. (2011b). Acta Cryst. E67, o1475-o1476.
Parthiban, P., Rathika, P., Park, K. S. & Jeong, Y. T. (2010b). Monatsh. Chem. 141, 79-93.
Parthiban, P., Rathika, P., Ramkumar, V., Son, S. M. & Jeong, Y. T. (2010a). Bioorg. Med. Chem. Lett. 20, 1642-1647.
Parthiban, P., Subalakshmi, V., Balasubramanian, K., Islam, Md. N., Choi, J. S. & Jeong, Y. T. (2011a). Bioorg. Med. Chem. Lett. 21, 2287-2296.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds