8-Bromo-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbo­nitrile

Suresh, G.; Srinivasan, J.; Bakthadoss, M.; Aravindhan, S.

doi:10.1107/S1600536813002511

Volume 69
Part 2
Page o312
February 2013

Received 28 December 2012
Accepted 24 January 2013
Online 31 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R = 0.047
wR = 0.102
Data-to-parameter ratio = 16.0
Details

8-Bromo-3-phenyl-3a,4-dihydro-3H-chromeno[4,3-c]isoxazole-3a-carbonitrile

G. Suresh,^a J. Srinivasan,^b M. Bakthadoss ^b and S. Aravindhan ^a ^*

^aDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, and ^bDepartment of Organic Chemistry, University of Madras, Chennai 600 025, India
Correspondence e-mail: aravindhanpresidency@gmail.com

In the title compound, C₁₇H₁₁BrN₂O₂, the five-membered isoxazole ring has an envelope conformation with the C atom bearing the phenyl ring as the flap. The pyran ring has a half-chair conformation. In the chromeno ring system, the dihedral angle between the mean plane of the pyran ring and the benzene ring is 4.68 (2)°. The dihedral angle between the mean planes of the chromeno ring system and the isoxazole ring is 13.79 (15)°. The latter forms a dihedral angle of 34.10 (17)° with the phenyl ring. In the crystal, molecules are linked by C-HN hydrogen bonds, forming an undulating two-dimensional network parallel to the ab plane.

Related literature

For the biological importance of 4H-chromene derivatives, see: Cai (2007, 2008); Cai et al. (2006); Caine (1993); Gabor (1988); Brooks (1998); Valenti et al. (1993); Hyana & Saimoto (1987); Tang et al. (2007). For related structures, see: Gangadharan et al. (2011); Swaminathan et al. (2011). For puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₇H₁₁BrN₂O₂
M_r = 355.19
Monoclinic, P 2₁ /c
a = 15.1034 (8) Å
b = 6.0676 (3) Å
c = 16.0865 (10) Å
= 99.953 (2)°
V = 1452.00 (14) Å³
Z = 4
Mo K radiation
= 2.84 mm^-1
T = 298 K
0.35 × 0.28 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.437, T_max = 0.601
9947 measured reflections
3175 independent reflections
2214 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.102
S = 1.09
3175 reflections
199 parameters
H-atom parameters constrained
_max = 0.68 e Å^-3
_min = -0.96 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2N2ⁱ	0.93	2.62	3.519 (5)	164
C15-H15N2ⁱⁱ	0.93	2.61	3.334 (5)	135
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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: SHELXL97 and PLATON.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2547 ).

Acknowledgements

GS and SA thank UGC, India, for financial support. GS also thanks the SAIF, IIT-Madras, for for the instrumentation facility.

References

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Caine, B. (1993). Science, 260, 1814-1816.
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Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.
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Swaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o905.
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Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.

organic compounds