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Volume 69 
Part 10 
Page o1533  
October 2013  

Received 18 August 2013
Accepted 26 August 2013
Online 12 September 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
R = 0.044
wR = 0.123
Data-to-parameter ratio = 25.2
Details
Open access

8-Bromo-3-(4-ethylphenyl)-1-phenyl-3,3a,4,9b-tetrahydro-1H-chromeno[4,3-c]isoxazole-3a-carbonitrile

aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601204, India,bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India,cDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India,dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram District, Chennai 603 203, Tamil Nadu, India, and eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

In the title compound, C25H21BrN2O2, the fused isoxazolidine ring adopts an envelope conformation with the N atom at the flap and the mean plane of the ring makes dihedral angles of 54.37 (12) and 87.32 (13)°, respectively, with the adjacent phenyl and benzene rings. The tetrahydropyran ring has a half-chair conformation. In the crystal, molecules are linked into a double-column structure along the b-axis direction through weak C-H...O and C-H...[pi] interactions.

Related literature

For the biological activity of cyanoacrylates, see: Zhang et al. (2009[Zhang, D., Zhang, X. & Guo, L. (2009). Acta Cryst. E65, o90.]); Obniska et al. (2005[Obniska, J., Jurczyk, S., Zejc, A., Kaminski, K., Tatarczynska, E. & Stachowicz, K. (2005). Pharmacol. Rep. 57, 170-175.]). For related structures, see: Ye et al. (2009[Ye, Y., Shen, W.-L. & Wei, X.-W. (2009). Acta Cryst. E65, o2636.]); Suresh et al. (2012[Suresh, G., Sabari, V., Srinivasan, J., Mannickam, B. & Aravindhan, S. (2012). Acta Cryst. E68, o570.]); Kanchanadevi et al. (2013[Kanchanadevi, J., Anbalagan, G., Selvakumar, R., Bakthadoss, M., Gunasekaran, B. & Manivannan, V. (2013). Acta Cryst. E69, o1354.]).

[Scheme 1]

Experimental

Crystal data
  • C25H21BrN2O2

  • Mr = 461.35

  • Triclinic, [P \overline 1]

  • a = 9.8813 (3) Å

  • b = 9.9921 (3) Å

  • c = 11.1587 (3) Å

  • [alpha] = 94.125 (2)°

  • [beta] = 92.196 (2)°

  • [gamma] = 101.500 (2)°

  • V = 1075.27 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.94 mm-1

  • T = 295 K

  • 0.25 × 0.20 × 0.15 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.620, Tmax = 0.748

  • 27480 measured reflections

  • 6895 independent reflections

  • 4405 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.123

  • S = 1.02

  • 6895 reflections

  • 274 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.54 e Å-3

  • [Delta][rho]min = -0.81 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg3, Cg4 and Cg5 are the centroids of the C1-C4/C8/C9, C10-C15 and C17-C22 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C11-H11...O1i 0.93 2.57 3.475 (2) 165
C3-H3...Cg5ii 0.93 2.78 3.491 (3) 134
C5-H5B...Cg3i 0.97 2.86 3.730 (4) 149
C22-H22...Cg4iii 0.93 2.95 3.628 (3) 131
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x, y+1, z; (iii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5299 ).


References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kanchanadevi, J., Anbalagan, G., Selvakumar, R., Bakthadoss, M., Gunasekaran, B. & Manivannan, V. (2013). Acta Cryst. E69, o1354.  [CSD] [CrossRef] [IUCr Journals]
Obniska, J., Jurczyk, S., Zejc, A., Kaminski, K., Tatarczynska, E. & Stachowicz, K. (2005). Pharmacol. Rep. 57, 170-175.  [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Suresh, G., Sabari, V., Srinivasan, J., Mannickam, B. & Aravindhan, S. (2012). Acta Cryst. E68, o570.  [CSD] [CrossRef] [IUCr Journals]
Ye, Y., Shen, W.-L. & Wei, X.-W. (2009). Acta Cryst. E65, o2636.  [CSD] [CrossRef] [IUCr Journals]
Zhang, D., Zhang, X. & Guo, L. (2009). Acta Cryst. E65, o90.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1533  [ doi:10.1107/S1600536813023982 ]

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