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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 [sigma](C-C) = 0.005 Å
R = 0.047
wR = 0.102
Data-to-parameter ratio = 16.0
Details
Open access

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

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-H...N 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[Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.], 2008[Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.]); Cai et al. (2006[Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.]); Caine (1993[Caine, B. (1993). Science, 260, 1814-1816.]); Gabor (1988[Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.]); Brooks (1998[Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.]); Valenti et al. (1993[Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.]); Hyana & Saimoto (1987[Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.]); Tang et al. (2007[Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.]). For related structures, see: Gangadharan et al. (2011[Gangadharan, R., SethuSankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o942.]); Swaminathan et al. (2011[Swaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o905.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H11BrN2O2

  • Mr = 355.19

  • Monoclinic, P 21 /c

  • a = 15.1034 (8) Å

  • b = 6.0676 (3) Å

  • c = 16.0865 (10) Å

  • [beta] = 99.953 (2)°

  • V = 1452.00 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.437, Tmax = 0.601

  • 9947 measured reflections

  • 3175 independent reflections

  • 2214 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.102

  • S = 1.09

  • 3175 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.68 e Å-3

  • [Delta][rho]min = -0.96 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...N2i 0.93 2.62 3.519 (5) 164
C15-H15...N2ii 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[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: 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

Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.  [CrossRef]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.  [PubMed]
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.  [ISI] [PubMed] [ChemPort]
Caine, B. (1993). Science, 260, 1814-1816.  [CrossRef] [ChemPort] [PubMed] [ISI]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.
Gangadharan, R., SethuSankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o942.  [CSD] [CrossRef] [details]
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Swaminathan, K., Sethusankar, K., Murugan, G. & Bakthadoss, M. (2011). Acta Cryst. E67, o905.  [CSD] [CrossRef] [details]
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.  [CSD] [CrossRef] [details]
Valenti, P., Da Re, P., Rampa, A., Montanari, P., Carrara, M. & Cima, L. (1993). Anticancer Drug. Des. 8, 349-360.  [ChemPort] [PubMed]


Acta Cryst (2013). E69, o312  [ doi:10.1107/S1600536813002511 ]

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