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Volume 69 
Part 1 
Page o105  
January 2013  

Received 9 December 2012
Accepted 13 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.057
wR = 0.143
Data-to-parameter ratio = 14.0
Details
Open access

2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoromethyl)phenyl]-1,4,5,6,7,8-hexahydroquinoline-3-carbonitrile

aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, and bDepartment of Chemistry, Shivaji University, Kolhapur 416 004 (MS), India
Correspondence e-mail: rkvk.paper11@gmail.com

In the title molecule, C19H18F3N3O, the dihydropyridine and cyclohexene rings both adopt sofa conformations. The five essentially planar atoms of the dihydropyridine ring [maximum deviation = 0.039 (2) Å] form a dihedral angle of 88.19 (8)° with the benzene ring. The F atoms of the trifluoromethyl group were refined as disordered over two sets of sites in a 0.840 (3):0.160 (3) ratio. In the crystal, N-H...O and N-H...N hydrogen bonds link molecules into a two-dimensional network parallel to (100).

Related literature

For applications of dihydropyridines, see: Mayler et al. (1989[Mayler, W. G. (1989). In Calcium Antagonist. London: Academic Press.]); Triggle et al.(1989[Triggle, D. J., Langs, D. A. & Jamis, R. A. (1989). Med. Res. Rev. 9, 123-180.]); Leon et al. (2008[Leon, R., Rios, C., Contelles, J. M., Lopez, G. M., Garcia, A. G. & Villarroya, M. (2008). Eur. J. Med. Chem. 43, 668-674.]). For related structures, see: Jiang et al. (2006[Jiang, H., Wang, X.-S., Zhang, M.-M., Li, Y.-L. & Shi, D.-Q. (2006). Acta Cryst. E62, o1184-o1186.]); Tu et al. (2005[Tu, S., Zhang, J., Zhu, X., Xu, J. & Wang, Q. (2005). Acta Cryst. E61, o983-o985.]). For ring conformations, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). In Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18F3N3O

  • Mr = 361.36

  • Monoclinic, C 2/c

  • a = 24.2434 (6) Å

  • b = 9.6030 (2) Å

  • c = 15.2426 (4) Å

  • [beta] = 93.960 (2)°

  • V = 3540.15 (15) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.896, Tmax = 1.000

  • 42194 measured reflections

  • 3469 independent reflections

  • 2462 reflections with I > 2[sigma](I)

  • Rint = 0.059

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.143

  • S = 1.03

  • 3469 reflections

  • 247 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.86 2.39 3.117 (2) 143
N16-H16A...N20ii 0.86 2.12 2.966 (3) 168
N16-H16B...O1i 0.86 2.08 2.897 (2) 158
Symmetry codes: (i) [x, -y+1, z+{\script{1\over 2}}]; (ii) -x, -y+2, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5570 ).


Acknowledgements

RK acknowledges the Department of Science & Technology for access to the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

Duax, W. L. & Norton, D. A. (1975). In Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jiang, H., Wang, X.-S., Zhang, M.-M., Li, Y.-L. & Shi, D.-Q. (2006). Acta Cryst. E62, o1184-o1186.  [CrossRef] [details]
Leon, R., Rios, C., Contelles, J. M., Lopez, G. M., Garcia, A. G. & Villarroya, M. (2008). Eur. J. Med. Chem. 43, 668-674.  [ISI] [PubMed] [ChemPort]
Mayler, W. G. (1989). In Calcium Antagonist. London: Academic Press.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Triggle, D. J., Langs, D. A. & Jamis, R. A. (1989). Med. Res. Rev. 9, 123-180.  [CrossRef] [ChemPort] [PubMed] [ISI]
Tu, S., Zhang, J., Zhu, X., Xu, J. & Wang, Q. (2005). Acta Cryst. E61, o983-o985.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o105  [ doi:10.1107/S1600536812050684 ]

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