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Volume 69 
Part 3 
Pages o417-o418  
March 2013  

Received 11 February 2013
Accepted 15 February 2013
Online 20 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.061
wR = 0.126
Data-to-parameter ratio = 13.4
Details
Open access

2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoromethyl)phenyl]-5,6,7,8-tetrahydro-4H-chromene-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, C19H17F3N2O2, the fused cyclohexene and pyran rings adopt sofa and flattened boat conformations, respectively. The four essentially planar atoms of the pyran ring [maximum deviation = 0.008 (2) Å] form a dihedral angle of 88.13 (9)° with the benzene ring. The F atoms of the trifluoromethyl group were refined as disordered over three sets of sites in a 0.507 (7):0.330 (7):0.163 (3) ratio. In the crystal, molecules are connected into inversion dimers via pairs of N-H...N hydrogen bonds and these dimers are further linked by N-H...O hydrogen bonds into a two-dimensional network parallel to (100).

Related literature

For the biological activity of 4H-pyran derivatives, see: Bhattacharyya et al.(2012[Bhattacharyya, P., Pradhan, K., Paul, S. & Das, A. S. (2012). Tetrahedron Lett. 53, 4687-4691.]); Khaksar et al. (2012[Khaksar, S., Rouhollahpour, A. & Talesh, S. M. (2012). J. Fluorine Chem. 141, 12-15.]); Fotouhi et al. (2007[Fotouhi, L., Heravi, M. M., Fatehi, A. & Bakhtiari, K. (2007). Tetrahedron Lett. 48, 5379-5381.]). For related structures, see: Wang (2011[Wang, X. (2011). Acta Cryst. E67, o832.]); Anthal et al. (2012[Anthal, S., Brahmachari, G., Laskar, S., Banerjee, B., Kant, R. & Gupta, V. K. (2012). Acta Cryst. E68, o2592-o2593.]); Kant et al. (2013[Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Mulik, A. G. & Deshmukh, M. B. (2013). Acta Cryst. E69, o105.]). For ring conformations, see: Duax & Norton (1975[Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.]).

[Scheme 1]

Experimental

Crystal data
  • C19H17F3N2O2

  • Mr = 362.35

  • Monoclinic, C 2/c

  • a = 23.7543 (6) Å

  • b = 9.3871 (2) Å

  • c = 15.8857 (4) Å

  • [beta] = 94.704 (2)°

  • V = 3530.33 (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 = 0.766, Tmax = 1.000

  • 40937 measured reflections

  • 3467 independent reflections

  • 2538 reflections with I > 2[sigma](I)

  • Rint = 0.065

Refinement
  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.126

  • S = 1.03

  • 3467 reflections

  • 258 parameters

  • 10 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N21-H21A...N20i 0.86 2.17 3.025 (3) 171
N21-H21B...O2ii 0.86 2.10 2.934 (2) 163
Symmetry codes: (i) -x, -y+2, -z+2; (ii) [x, -y+1, z+{\script{1\over 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 for Windows (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: LH5585 ).


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

Anthal, S., Brahmachari, G., Laskar, S., Banerjee, B., Kant, R. & Gupta, V. K. (2012). Acta Cryst. E68, o2592-o2593.  [CSD] [CrossRef] [details]
Bhattacharyya, P., Pradhan, K., Paul, S. & Das, A. S. (2012). Tetrahedron Lett. 53, 4687-4691.  [ISI] [CSD] [CrossRef] [ChemPort]
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Fotouhi, L., Heravi, M. M., Fatehi, A. & Bakhtiari, K. (2007). Tetrahedron Lett. 48, 5379-5381.  [ISI] [CrossRef] [ChemPort]
Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Mulik, A. G. & Deshmukh, M. B. (2013). Acta Cryst. E69, o105.  [CSD] [CrossRef] [details]
Khaksar, S., Rouhollahpour, A. & Talesh, S. M. (2012). J. Fluorine Chem. 141, 12-15.  [ISI] [CrossRef]
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]
Wang, X. (2011). Acta Cryst. E67, o832.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o417-o418   [ doi:10.1107/S1600536813004522 ]

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