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Volume 69 
Part 6 
Page o882  
June 2013  

Received 18 March 2013
Accepted 6 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.099
Data-to-parameter ratio = 12.9
Details
Open access

4-(Adamantan-1-yl)-2-(4-fluorophenyl)quinoline

aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín, 762 72, Czech Republic, and bDepartment of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
Correspondence e-mail: rvicha@ft.utb.cz

In the molecule of the title compound, C25H24FN, the dihedral angle between the best planes of the quinoline fragment (rings A and B) and the benzene ring (C) is 9.51 (4)°. In the crystal, molecules are linked into centrosymmetric dimers via pairs of weak C-H...F interactions. The molecules are stacked into chains along the a axis by weak off-set [pi]-[pi] interactions between the A and C rings of translation-related molecules with a centroid-centroid distance of 3.6440 (2) Å.

Related literature

For the preparation and spectroscopic properties of the title compound, see: Kozubková et al. (2012[Kozubková, Z., Rouchal, M., Necas, M. & Vícha, R. (2012). Helv. Chim. Acta, 95, 1003-1017.]). For related structures, see: Kozubková et al. (2012[Kozubková, Z., Rouchal, M., Necas, M. & Vícha, R. (2012). Helv. Chim. Acta, 95, 1003-1017.]); Prabhuswamy et al. (2012[Prabhuswamy, M., Swaroop, T. R., Madan Kumar, S., Rangappa, K. S. & Lokanath, N. K. (2012). Acta Cryst. E68, o3250.]). For the biological activity of related compounds, see: Nayyar et al. (2009[Nayyar, A., Patel, S. R., Shaikh, M., Coutinho, E. & Jain, R. (2009). Eur. J. Med. Chem. 44, 2017-2029.]).

[Scheme 1]

Experimental

Crystal data
  • C25H24FN

  • Mr = 357.45

  • Triclinic, [P \overline 1]

  • a = 6.4604 (3) Å

  • b = 10.9964 (4) Å

  • c = 12.9074 (5) Å

  • [alpha] = 93.205 (3)°

  • [beta] = 96.446 (3)°

  • [gamma] = 100.507 (3)°

  • V = 893.14 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 120 K

  • 0.60 × 0.40 × 0.20 mm

Data collection
  • Oxford Diffraction Xcalibur diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]) Tmin = 0.971, Tmax = 1.000

  • 9490 measured reflections

  • 3142 independent reflections

  • 2445 reflections with I > 2[sigma](I)

  • Rint = 0.015

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.099

  • S = 1.08

  • 3142 reflections

  • 244 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12...F1i 0.95 2.61 3.2955 (12) 129
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]); data reduction: CrysAlis RED; 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2093 ).


Acknowledgements

The financial support of this work by the Internal Founding Agency of Tomas Bata University in Zlin (project No. IGA/FT/2013/008) is gratefully acknowledged.

References

Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Kozubková, Z., Rouchal, M., Necas, M. & Vícha, R. (2012). Helv. Chim. Acta, 95, 1003-1017.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Nayyar, A., Patel, S. R., Shaikh, M., Coutinho, E. & Jain, R. (2009). Eur. J. Med. Chem. 44, 2017-2029.  [ISI] [CrossRef] [PubMed] [ChemPort]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Prabhuswamy, M., Swaroop, T. R., Madan Kumar, S., Rangappa, K. S. & Lokanath, N. K. (2012). Acta Cryst. E68, o3250.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o882  [ doi:10.1107/S1600536813012336 ]

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