2,4,6,8-Tetra­kis(2-fluoro­phen­yl)-3,7-diaza­bicyclo­[3.3.1]nonan-9-one

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

doi:10.1107/S1600536812051574

Volume 69
Part 2
Page o179
February 2013

Received 24 November 2012
Accepted 21 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.053
wR = 0.163
Data-to-parameter ratio = 15.1
Details

2,4,6,8-Tetrakis(2-fluorophenyl)-3,7-diazabicyclo[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 title compound, C₃₁H₂₄F₄N₂O, exists in a chair-boat conformation with an equatorial orientation of the 2-fluorophenyl groups on both sides of the secondary amino group of the chair form. The benzene rings in the `chair' part are inclined to each other at 19.4 (1)°, while the equivalent angle between the benzene rings in the `boat' part is 75.6 (1)°. One F atom was treated as disordered over two positions in a 0.838 (4):0.162 (4) ratio. In the crystal, N-HO hydrogen bonds link the molecules into chains along [001] and these chains are held together via weak N-HF and C-HF interactions.

Related literature

For the synthesis and stereochemistry of 3,7-diazabicyclo[3.3.1]nonan-9-ones, see: Parthiban et al. (2008). For the biological activity of 3,7-diazabicyclo[3.3.1]nonan-9-one derivatives and related structures, see: Park et al. (2012); Parthiban et al. (2009, 2010); Asakawa (1995); Jeyaraman & Avila (1981). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₃₁H₂₄F₄N₂O
M_r = 516.52
Monoclinic, P 2₁ /c
a = 12.5610 (11) Å
b = 15.9118 (13) Å
c = 13.0221 (8) Å
= 103.207 (3)°
V = 2533.9 (3) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.45 × 0.35 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004) T_min = 0.955, T_max = 0.978
18116 measured reflections
5466 independent reflections
3571 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.053
wR(F²) = 0.163
S = 1.05
5466 reflections
361 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.48 e Å^-3
_min = -0.40 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1NO1ⁱ	0.86 (2)	2.26 (2)	3.119 (2)	175.2 (19)
N2-H2NF1ⁱⁱ	0.92 (2)	2.46 (2)	3.332 (2)	158.4 (17)
C22-H22F4ⁱⁱⁱ	0.93	2.52	3.345 (3)	148
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y, -z+2.

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, 2012); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5368 ).

Acknowledgements

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

References

Asakawa, Y. (1995). In Progress in the Chemistry of Organic Natural Products, edited by G. W. Moore, R. E. Steglich & W. Tamm. New York: Springer-Verlag.
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. (2012). J. Appl. Cryst. 45, 849-854.
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.
Park, D. H., Ramkumar, V. & Parthiban, P. (2012). Acta Cryst. E68, o1481.
Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 6981-6985.
Parthiban, P., Kabilan, S., Ramkumar, V. & Jeong, Y. T. (2010). Bioorg. Med. Chem. Lett. 20, 6452-6458.
Parthiban, P., Ramachandran, R., Aridoss, G. & Kabilan, S. (2008). Magn. Reson. Chem. 46, 780-785.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds