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Volume 69 
Part 6 
Pages o857-o858  
June 2013  

Received 10 April 2013
Accepted 27 April 2013
Online 11 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.049
wR = 0.146
Data-to-parameter ratio = 12.4
Details
Open access

6'-(1,3-Diphenyl-1H-pyrazol-4-yl)-7'-(1H-indol-3-ylcarbonyl)-2-oxo-1-(prop-2-en-1-yl)-5',6',7',7a'-tetrahydro-1'H-spiro[indoline-3,5'-pyrrolo[1,2-c][1,3]thiazole]-7'-carbonitrile

aDepartment of Physics, S.M.K. Fomra Institute of Technology, Thaiyur, Chennai 603 103, India,bIndustrial Chemistry Laboratory, Central Leather Research Institute, Adyar, Chennai 600 020, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
Correspondence e-mail: a_sp59@yahoo.in

In the title compound, C41H32N6O2S, the pyrrolothiazole ring system is folded about the bridging N-C bond. The thiazolidine and pyrrolidine rings adopt envelope (with the fused C atom as the flap) and twisted conformations, respectively. The two phenyl rings attached to the pyrazole ring are twisted from the plane of the latter by 6.8 (1) and 52.8 (1)°. The allyl group is disordered over two conformations in a 0.805 (6):0.195 (6) ratio. In the crystal, pairs of N-H...O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For the biological activity of spiroheterocycles, see: Kilonda et al. (1995[Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820-5824.]); Ferguson et al. (2005[Ferguson, N. M., Cummings, D. A. T., Cauchemez, S., Fraser, C., Riley, S., Meeyai, A., Iamsirithaworn, S. & Burke, D. S. (2005). Nature (London), 437, 209-214.]). For related structures, see: Jagadeesan et al. (2012a[Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012a). Acta Cryst. E68, o382-o383.],b[Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012b). Acta Cryst. E68, o2505-o2506.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C41H32N6O2S

  • Mr = 672.80

  • Monoclinic, P 21 /n

  • a = 10.7396 (10) Å

  • b = 16.3471 (14) Å

  • c = 20.112 (2) Å

  • [beta] = 105.485 (4)°

  • V = 3402.7 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.14 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.972

  • 25634 measured reflections

  • 5983 independent reflections

  • 3281 reflections with I > 2[sigma](I)

  • Rint = 0.049

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.146

  • S = 1.06

  • 5983 reflections

  • 483 parameters

  • 48 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N5-H5A...O1i 0.92 (4) 1.92 (4) 2.822 (4) 166 (3)
Symmetry code: (i) -x, -y, -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: CV5404 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and BioPhysics, University of Madras, Chennai, India, for the data collection.

References

Bruker. (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
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]
Ferguson, N. M., Cummings, D. A. T., Cauchemez, S., Fraser, C., Riley, S., Meeyai, A., Iamsirithaworn, S. & Burke, D. S. (2005). Nature (London), 437, 209-214.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012a). Acta Cryst. E68, o382-o383.  [CSD] [CrossRef] [ChemPort] [details]
Jagadeesan, G., Sethusankar, K., Prasanna, R. & Raghunathan, R. (2012b). Acta Cryst. E68, o2505-o2506.  [CSD] [CrossRef] [ChemPort] [details]
Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820-5824.  [CrossRef] [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, o857-o858   [ doi:10.1107/S1600536813011513 ]

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