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Volume 69 
Part 10 
Page o1525  
October 2013  

Received 3 August 2013
Accepted 4 September 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.125
Data-to-parameter ratio = 13.5
Details
Open access

2,4-Bis(4-fluorophenyl)-1,5-dimethyl-3-azabicyclo[3.3.1]nonan-9-one

aDepartment of Physics, Seethalakshmi Ramaswami College (Autonomous), Tiruchirappalli 620 002, India,bDepartment of Physics, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli 621 112, India, and cDepartment of Chemistry, Annamalai University, Annamalai Nagar 608 002, India
Correspondence e-mail: raghema2000@yahoo.co.in

The asymmetric unit of the title compound, C22H23F2NO, contains two independent molecules, A and B. The bicyclic system adopts a twin-chair conformation in both molecules. The dihedral angles between the fluorophenyl rings are 55.27 (8) and 56.37 (7)° in molecules A and B, respectively. The NH groups are not involved in hydrogen bonding due to the steric hindrance of fluorophenyl groups. The crystal structure features weak C-H...O interactions.

Related literature

For related structures, see: Venkateswaramoorthi et al. (2013[Venkateswaramoorthi, R., Rizwana Begum, S., Hema, R., Krishnasamy, K. & Anitha, A. G. (2013). Acta Cryst. E69, o768.]); Pham et al. (1998[Pham, M., Gdaniec, M. & Polonski, T. (1998). J. Org. Chem. 63, 3731-3734.]). For the synthesis of 1,5-dimethyl-2,4-diphenyl-3-azabicyclo[3.3.1]nonan-9-one derivatives, see: Venkateswaramoorthi et al. (2012[Venkateswaramoorthi, R., Xavier, J. J. F., Krishnasamy, K. & Saleem, H. (2012). J. Mol. Struct. 1012, 119-125.]). 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
  • C22H23F2NO

  • Mr = 355.41

  • Monoclinic, P 21 /n

  • a = 8.8470 (3) Å

  • b = 20.5656 (8) Å

  • c = 20.6403 (9) Å

  • [beta] = 98.633 (2)°

  • V = 3712.8 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.35 × 0.35 × 0.30 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.973

  • 32409 measured reflections

  • 6363 independent reflections

  • 3974 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.125

  • S = 1.01

  • 6363 reflections

  • 473 parameters

  • 3 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18...O2i 0.93 2.50 3.395 (3) 163
C44-H44...O1ii 0.93 2.47 3.369 (3) 161
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (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: BH2483 ).


Acknowledgements

The authors are thankful to the SAIF, IIT Madras, for the data collection. SR thanks the University Grants Commission for the financial support of this work (MRP-4335/12).

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Pham, M., Gdaniec, M. & Polonski, T. (1998). J. Org. Chem. 63, 3731-3734.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Venkateswaramoorthi, R., Rizwana Begum, S., Hema, R., Krishnasamy, K. & Anitha, A. G. (2013). Acta Cryst. E69, o768.  [CSD] [CrossRef] [IUCr Journals]
Venkateswaramoorthi, R., Xavier, J. J. F., Krishnasamy, K. & Saleem, H. (2012). J. Mol. Struct. 1012, 119-125.  [Web of Science] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o1525  [ doi:10.1107/S1600536813024689 ]

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