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Volume 69 
Part 7 
Page o1035  
July 2013  

Received 28 May 2013
Accepted 1 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.129
Data-to-parameter ratio = 13.0
Details
Open access

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

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,dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203, Tamil Nadu, India,eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India, and fDepartment of Organic Chemistry, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: phdguna@gmail.com, crystallography2010@gmail.com

In the title compound, C33H26N2O4, the pyrazole ring makes dihedral angles of 15.13 (7) and 60.80 (7)° with the adjacent phenyl rings. Both dihydropyran rings exhibit half-chair conformations. A weak intramolecular C-H...O interaction occurs. In the crystal, molecules are linked into inversion dimers through pairs of C-H...N interactions. Weak C-H...[pi] interactions are also observed.

Related literature

For the biological activity 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 a related structure, see: Ponnusamy et al. (2013[Ponnusamy, R., Sabari, V., Sivakumar, G., Bakthadoss, M. & Aravindhan, S. (2013). Acta Cryst. E69, o267-o268.]).

[Scheme 1]

Experimental

Crystal data
  • C33H26N2O4

  • Mr = 514.56

  • Monoclinic, P 21 /n

  • a = 11.916 (5) Å

  • b = 10.876 (5) Å

  • c = 21.153 (5) Å

  • [beta] = 105.797 (5)°

  • V = 2637.9 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 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

  • 40448 measured reflections

  • 4605 independent reflections

  • 3289 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.129

  • S = 1.01

  • 4605 reflections

  • 354 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg4 and Cg6 are the centroids of the N1/N2/C7/C24/C25, C1-C6 and C17-C22 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C18-H18...N2i 0.93 2.62 3.517 (3) 163
C6-H6...O1 0.93 2.26 2.877 (2) 123
C13-H13...Cg6ii 0.93 2.98 3.904 (8) 174
C18-H18...Cg1i 0.93 2.88 3.720 (5) 150
C23-H23...Cg4iii 0.98 2.86 3.787 (6) 159
Symmetry codes: (i) -x, -y+1, -z; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x, -y+2, -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: IS5278 ).


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.
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, o1035  [ doi:10.1107/S1600536813015213 ]

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