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Volume 69 
Part 3 
Page o317  
March 2013  

Received 18 December 2012
Accepted 21 January 2013
Online 2 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.002 Å
R = 0.055
wR = 0.166
Data-to-parameter ratio = 23.0
Details
Open access

1'-(1,3-Diphenyl-1H-pyrazol-4-yl)-1''-methyl-2',3',5',6',7',7a'-octahydro-1'H-dispiro[1-benzopyran-3,2'-pyrrolizine-3',3''-indoline]-2'',4-dione

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

In the title compound C38H32N4O3, one pyrrolidine ring adopts an envelope conformation with the N atom as the flap while other pyrrolidine ring adopts an twisted conformation. The pyrrolizine ring forms dihedral angles of 79.24 (5) and 77.57 (5)° with the chromene and indole rings, respectively. The carbonyl O atoms deviate from the least-square planes through the chromene and indole rings by 0.0113 (12) and 0.0247 (12) Å, respectively. In the crystal, non-classical C-H...O interactions link the molecules, generating an C(9) chain along the b-axis direction.

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: Fun et al. (2011[Fun, H.-K., Chia, T. S., Malladi, S., Isloor, A. M. & Shivananda, K. N. (2011). Acta Cryst. E67, o2822-o2823.]). 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
  • C38H32N4O3

  • Mr = 592.68

  • Triclinic, [P \overline 1]

  • a = 10.8240 (3) Å

  • b = 10.8382 (3) Å

  • c = 13.9127 (4) Å

  • [alpha] = 70.290 (1)°

  • [beta] = 88.946 (2)°

  • [gamma] = 73.578 (1)°

  • V = 1468.47 (7) 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

  • 35301 measured reflections

  • 9340 independent reflections

  • 5865 reflections with I > 2[sigma](I)

  • Rint = 0.032

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

  • wR(F2) = 0.166

  • S = 1.06

  • 9340 reflections

  • 406 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C34-H33...O3i 0.93 2.59 3.523 (3) 178
Symmetry code: (i) x, y+1, z.

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; 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 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) 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: RK2391 ).


Acknowledgements

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

References

Baraldi, P. G., Manfredini, S., Romagnoli, R., Stevanato, L., Zaid, A. N. & Manservigi, R. (1998). Nucleosides Nucleotides, 17, 2165-2171.  [CrossRef] [ChemPort]
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]
Fun, H.-K., Chia, T. S., Malladi, S., Isloor, A. M. & Shivananda, K. N. (2011). Acta Cryst. E67, o2822-o2823.  [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] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o317  [ doi:10.1107/S1600536813002043 ]

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