[Journal logo]

Volume 69 
Part 5 
Page o711  
May 2013  

Received 27 February 2013
Accepted 8 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.055
wR = 0.166
Data-to-parameter ratio = 21.7
Details
Open access

1'-(1,3-Diphenyl-1H-pyrazol-4-yl)-2',3',5',6',7',7a'-hexahydro-1'H-dispiro[acenaphthylene-1,3'-pyrrolizine-2',3''-chromane]-2,4''(1H)-dione

aDepartment of Physics, Meenakshi College of Engineering, West K.K. Nagar, Chennai 600 078, India,bIndustrial Chemistry Lab, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
Correspondence e-mail: ksethusankar@yahoo.co.in

In the title compound, C41H31N3O3, the pyrazole and pyrrolidine rings adopt twisted conformations. The mean plane of the pyrazole ring forms dihedral angles of 9.11 (12) and 39.65 (11)° with the phenyl rings. The O atoms deviate from the mean planes of the chromene and acenaphthylene ring systems by 0.194 (15) and 0.079 (15) Å, respectively. In the crystal, molecules are linked via pairs of C-H...O interactions,forming inversion dimers with an R22(12) ring motif.

Related literature

For the biological activity of pyrazole derivatives, see: Mahajan et al. (1991[Mahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245-249.]); Baraldi et al. (1998[Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.]); Katayama & Oshiyama (1997[Katayama, H. & Oshiyama, T. (1997). Can. J. Chem. 75, 913-919.]); Chen & Li (1998[Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572-576.]). For a related structure, see: Jagadeesan et al. (2013[Jagadeesan, G., Sethusankar, K., Kathirvelan, D., Haribabu, J. & Reddy, B. S. R. (2013). Acta Cryst. E69, o317.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C41H31N3O3

  • Mr = 613.69

  • Triclinic, [P \overline 1]

  • a = 10.0183 (4) Å

  • b = 12.7374 (5) Å

  • c = 13.2489 (5) Å

  • [alpha] = 114.365 (2)°

  • [beta] = 96.960 (2)°

  • [gamma] = 92.281 (2)°

  • V = 1521.17 (11) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.975, Tmax = 0.983

  • 32812 measured reflections

  • 9207 independent reflections

  • 5094 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.166

  • S = 1.01

  • 9207 reflections

  • 424 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C22-H22...O3i 0.98 2.47 3.273 (2) 138
Symmetry code: (i) -x, -y+1, -z+1.

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.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2396 ).


Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection. KS thanks the University Grant Commission (UGC), India, for a Minor Research Project.

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.  [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, H. S. & Li, Z. M. (1998). Chem. J. Chin. Univ. 19, 572-576.  [ChemPort]
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]
Jagadeesan, G., Sethusankar, K., Kathirvelan, D., Haribabu, J. & Reddy, B. S. R. (2013). Acta Cryst. E69, o317.  [CSD] [CrossRef] [details]
Katayama, H. & Oshiyama, T. (1997). Can. J. Chem. 75, 913-919.  [CrossRef] [ChemPort] [ISI]
Mahajan, R. N., Havaldar, F. H. & Fernandes, P. S. (1991). J. Indian Chem. Soc. 68, 245-249.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o711  [ doi:10.1107/S1600536813009562 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.