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

Parthiban, P.; Ramkumar, V.; Kim, M.S.; Lim, K.T.; Jeong, Y.T.

doi:10.1107/S1600536808036660

Volume 64
Part 12
Page o2332
December 2008

Received 6 November 2008
Accepted 7 November 2008
Online 13 November 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.042
wR = 0.103
Data-to-parameter ratio = 19.4
Details

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

P. Parthiban,^a V. Ramkumar,^b Min Sung Kim,^a Kwon Taek Lim ^a and Yeon Tae Jeong ^a ^*

^aDivision of Image Science and Information Engineering, Pukyong National University, Busan 608 739, Republic of Korea, and ^bDepartment of Chemistry, IIT Madras, Chennai, Tamilnadu, India
Correspondence e-mail: ytjeong@pknu.ac.kr

The complete molecule of the title compound, C₂₀H₁₉Br₂NO, is generated by crystallographic mirror symmetry, with two C, one O and one N atom lying on the mirror plane. The compound exists in a twin-chair conformation with equatorial dispositions of the 3-bromophenyl groups [dihedral angle between rings = 27.37 (3)°]. The packing is stabilized by weak N-HO and C-HO interactions.

Related literature

For background, see: Barker et al. (2005); Jeyaraman & Avila (1981); Padegimas & Kovacic (1972); Smith-Verdier et al. (1983). For a similiar structure, see: Parthiban et al. (2008). For puckering parameters, see: Cremer & Pople (1975); Web & Becker (1967).

Experimental

Crystal data

C₂₀H₁₉Br₂NO
M_r = 449.18
Orthorhombic, P n m a
a = 7.1595 (6) Å
b = 24.5891 (19) Å
c = 10.2598 (6) Å
V = 1806.2 (2) Å³
Z = 4
Mo K radiation
= 4.49 mm^-1
T = 298 (2) K
0.34 × 0.25 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999) T_min = 0.310, T_max = 0.498 (expected range = 0.277-0.445)
12758 measured reflections
2286 independent reflections
1554 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.103
S = 1.05
2286 reflections
118 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.84 e Å^-3
_min = -0.71 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1AO1ⁱ	0.87 (5)	2.41 (5)	3.168 (5)	145 (4)
C1-H1O1ⁱⁱ	0.98	2.54	3.361 (4)	142
Symmetry codes: (i) x-1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+{\script{5\over 2}}]$ .

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2838 ).

Acknowledgements

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

References

Barker, D., Lin, D. H. S., Carland, J. E., Chu, C. P. Y., Chebib, M., Brimble, M. A., Savage, G. P. & McLeod, M. D. (2005). Bioorg. Med. Chem. 13, 4565-4575.
Bruker (1999). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.
Padegimas, S. J. & Kovacic, P. (1972). J. Org. Chem. 37, 2672-2676.
Parthiban, P., Ramkumar, V., Kim, M. S., Lim, K. T. & Jeong, Y. T. (2008). Acta Cryst. E64, o1586.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith-Verdier, P., Florencio, F. & García-Blanco, S. (1983). Acta Cryst. C39, 101-103.
Web, N. C. & Becker, M. R. (1967). J. Chem. Soc. B, pp. 1317-1321.

organic compounds