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Volume 69 
Part 12 
Page o1746  
December 2013  

Received 21 October 2013
Accepted 31 October 2013
Online 6 November 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.043
wR = 0.133
Data-to-parameter ratio = 13.8
Details
Open access

16-Methyl-11-(2-methyl­phen­yl)-14-phenyl-8,12-dioxa-14,15-di­aza­tetra­cyclo­[8.7.0.02,7.013,17]hepta­deca-2(7),3,5,13(17),15-penta­ene-10-carbo­nitrile

aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India,bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India,cDepartment of Organic Chemistry, University of Madras, Guindy campus, Chennai 600 025, India, and dDepartment 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, C28H23N3O2, the pyrazole ring makes a dihedral angle of 16.90 (6)° with the phenyl ring to which it is attached. Both di­hydro­pyran rings exhibit half-chair conformations. Intramolecular C-H...O interactions generate S(6) and S(8) ring motifs. In the crystal, weak C-H...O and C-H...[pi] interactions occur.

Related literature

For the biological activities of 4H-chromenes see: Cai et al. (2006[Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.]); 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.]); 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: Ponnusamy et al. (2013[Ponnusamy, R., Sabari, V., Sivakumar, G., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o267-o268.]); Kanchanadevi et al. (2013[Kanchanadevi, J., Anbalagan, G., Kannan, D., Gunasekaran, B., Manivannan, V. & Bakthadoss, N. (2013). Acta Cryst. E69, o1035.]).

[Scheme 1]

Experimental

Crystal data
  • C28H23N3O2

  • Mr = 433.49

  • Triclinic, [P \overline 1]

  • a = 9.021 (5) Å

  • b = 9.604 (5) Å

  • c = 15.254 (5) Å

  • [alpha] = 72.720 (5)°

  • [beta] = 76.997 (5)°

  • [gamma] = 63.875 (5)°

  • V = 1126.1 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.980, Tmax = 0.983

  • 20066 measured reflections

  • 4154 independent reflections

  • 3085 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.133

  • S = 1.03

  • 4154 reflections

  • 300 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C6-H6...O1 0.93 2.37 2.952 (2) 120
C28-H28C...O2 0.96 2.47 3.310 (3) 146
C16-H16A...O2i 0.97 2.56 3.380 (2) 143
C20-H20...Cg1ii 0.96 2.86 3.567 (3) 134
Symmetry codes: (i) -x, -y, -z+2; (ii) x-1, y+1, z.

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: BT6941 ).


References

Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.  [CrossRef]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.  [Web of Science] [PubMed] [ChemPort]
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.
Kanchanadevi, J., Anbalagan, G., Kannan, D., Gunasekaran, B., Manivannan, V. & Bakthadoss, N. (2013). Acta Cryst. E69, o1035.  [CSD] [CrossRef] [IUCr Journals]
Ponnusamy, R., Sabari, V., Sivakumar, G., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o267-o268.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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]
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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, o1746  [ doi:10.1107/S1600536813029905 ]

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