2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoro­meth­yl)phen­yl]-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile

Kant, R.; Gupta, V.K.; Kapoor, K.; Patil, D.R.; Chandam, D.R.; Deshmukh, M.B.

doi:10.1107/S1600536813004522

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.061
wR = 0.126
Data-to-parameter ratio = 13.4
Details

2-Amino-7,7-dimethyl-5-oxo-4-[3-(trifluoromethyl)phenyl]-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

Rajni Kant,^a ^* Vivek K. Gupta,^a Kamini Kapoor,^a D. R. Patil,^b D. R. Chandam ^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, 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-HN hydrogen bonds and these dimers are further linked by N-HO 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); Khaksar et al. (2012); Fotouhi et al. (2007). For related structures, see: Wang (2011); Anthal et al. (2012); Kant et al. (2013). For ring conformations, see: Duax & Norton (1975).

Experimental

Crystal data

C₁₉H₁₇F₃N₂O₂
M_r = 362.35
Monoclinic, C 2/c
a = 23.7543 (6) Å
b = 9.3871 (2) Å
c = 15.8857 (4) Å
= 94.704 (2)°
V = 3530.33 (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 = 0.766, T_max = 1.000
40937 measured reflections
3467 independent reflections
2538 reflections with I > 2(I)
R_int = 0.065

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.126
S = 1.03
3467 reflections
258 parameters
10 restraints
H-atom parameters constrained
_max = 0.26 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N21-H21AN20ⁱ	0.86	2.17	3.025 (3)	171
N21-H21BO2ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (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: 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.
Bhattacharyya, P., Pradhan, K., Paul, S. & Das, A. S. (2012). Tetrahedron Lett. 53, 4687-4691.
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.
Fotouhi, L., Heravi, M. M., Fatehi, A. & Bakhtiari, K. (2007). Tetrahedron Lett. 48, 5379-5381.
Kant, R., Gupta, V. K., Kapoor, K., Patil, D. R., Mulik, A. G. & Deshmukh, M. B. (2013). Acta Cryst. E69, o105.
Khaksar, S., Rouhollahpour, A. & Talesh, S. M. (2012). J. Fluorine Chem. 141, 12-15.
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.
Wang, X. (2011). Acta Cryst. E67, o832.

organic compounds