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

Kant, R.; Gupta, V.K.; Kapoor, K.; Patil, D.R.; Mulik, A.G.; Deshmukh, M.B.

doi:10.1107/S1600536812050684

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.057
wR = 0.143
Data-to-parameter ratio = 14.0
Details

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

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a D. R. Patil,^b A. G. Mulik ^b and Madhukar B. Deshmukh ^b

^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-HO and N-HN hydrogen bonds link molecules into a two-dimensional network parallel to (100).

Related literature

For applications of dihydropyridines, see: Mayler et al. (1989); Triggle et al.(1989); Leon et al. (2008). For related structures, see: Jiang et al. (2006); Tu et al. (2005). For ring conformations, see: Duax & Norton (1975).

Experimental

Crystal data

C₁₉H₁₈F₃N₃O
M_r = 361.36
Monoclinic, C 2/c
a = 24.2434 (6) Å
b = 9.6030 (2) Å
c = 15.2426 (4) Å
= 93.960 (2)°
V = 3540.15 (15) Å³
Z = 8
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.896, T_max = 1.000
42194 measured reflections
3469 independent reflections
2462 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.143
S = 1.03
3469 reflections
247 parameters
6 restraints
H-atom parameters constrained
_max = 0.31 e Å^-3
_min = -0.39 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.86	2.39	3.117 (2)	143
N16-H16AN20ⁱⁱ	0.86	2.12	2.966 (3)	168
N16-H16BO1ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and PLATON (Spek, 2009); 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.
Jiang, H., Wang, X.-S., Zhang, M.-M., Li, Y.-L. & Shi, D.-Q. (2006). Acta Cryst. E62, o1184-o1186.
Leon, R., Rios, C., Contelles, J. M., Lopez, G. M., Garcia, A. G. & Villarroya, M. (2008). Eur. J. Med. Chem. 43, 668-674.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Triggle, D. J., Langs, D. A. & Jamis, R. A. (1989). Med. Res. Rev. 9, 123-180.
Tu, S., Zhang, J., Zhu, X., Xu, J. & Wang, Q. (2005). Acta Cryst. E61, o983-o985.