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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 [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.053
wR = 0.163
Data-to-parameter ratio = 15.1
Details
Open access

2,4,6,8-Tetrakis(2-fluorophenyl)-3,7-diazabicyclo[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 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-H...O hydrogen bonds link the molecules into chains along [001] and these chains are held together via weak N-H...F and C-H...F interactions.

Related literature

For the synthesis and stereochemistry of 3,7-diazabicyclo[3.3.1]nonan-9-ones, see: Parthiban et al. (2008[Parthiban, P., Ramachandran, R., Aridoss, G. & Kabilan, S. (2008). Magn. Reson. Chem. 46, 780-785.]). For the biological activity of 3,7-diazabicyclo[3.3.1]nonan-9-one derivatives and related structures, see: Park et al. (2012[Park, D. H., Ramkumar, V. & Parthiban, P. (2012). Acta Cryst. E68, o1481.]); Parthiban et al. (2009[Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 6981-6985.], 2010[Parthiban, P., Kabilan, S., Ramkumar, V. & Jeong, Y. T. (2010). Bioorg. Med. Chem. Lett. 20, 6452-6458.]); Asakawa (1995[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.]); Jeyaraman & Avila (1981[Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C31H24F4N2O

  • Mr = 516.52

  • Monoclinic, P 21 /c

  • a = 12.5610 (11) Å

  • b = 15.9118 (13) Å

  • c = 13.0221 (8) Å

  • [beta] = 103.207 (3)°

  • V = 2533.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2004). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.955, Tmax = 0.978

  • 18116 measured reflections

  • 5466 independent reflections

  • 3571 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N...O1i 0.86 (2) 2.26 (2) 3.119 (2) 175.2 (19)
N2-H2N...F1ii 0.92 (2) 2.46 (2) 3.332 (2) 158.4 (17)
C22-H22...F4iii 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[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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jeyaraman, R. & Avila, S. (1981). Chem. Rev. 81, 149-174.  [CrossRef] [ChemPort] [ISI]
Park, D. H., Ramkumar, V. & Parthiban, P. (2012). Acta Cryst. E68, o1481.  [CSD] [CrossRef] [details]
Parthiban, P., Aridoss, G., Rathika, P., Ramkumar, V. & Kabilan, S. (2009). Bioorg. Med. Chem. Lett. 19, 6981-6985.  [CSD] [CrossRef] [PubMed] [ChemPort]
Parthiban, P., Kabilan, S., Ramkumar, V. & Jeong, Y. T. (2010). Bioorg. Med. Chem. Lett. 20, 6452-6458.  [CSD] [CrossRef] [ChemPort] [PubMed]
Parthiban, P., Ramachandran, R., Aridoss, G. & Kabilan, S. (2008). Magn. Reson. Chem. 46, 780-785.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o179  [ doi:10.1107/S1600536812051574 ]

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