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Volume 69 
Part 4 
Pages o493-o494  
April 2013  

Received 27 February 2013
Accepted 28 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.049
wR = 0.154
Data-to-parameter ratio = 22.7
Details
Open access

(6'R*,7'R*)-7'-(1,3,-Diphenyl-1H-pyrazol-4-yl)-1,2,5',6',7',7a',3'',4''-octahydro-1'H,2''H-dispiro[acenaphthylene-1,5'-pyrrolo[1,2-c][1,3]thiazole-6',3''-[1]benzopyran]-2,4''-dione

aDepartment of Physics, Sree Krishna College of Engineering, Anicut, Vellore 632 001, India,bIndustrial Chemistry Labratory, Central Leather Research Institute, Adyar, Chennai 600 020, India,cDepartment of Physics, Mahendra Engineering College, Namakkal 637 503, India, and dDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
Correspondence e-mail: smurugavel27@gmail.com

In the title compound, C40H29N3O3S, the pyran ring adopts a sofa conformation, the thiazolidine ring adopts a twisted conformation and the pyrrolidine ring adopts an envelope conformation with the N atom as the flap. The pyrazole ring is essentially planar [maximum deviation = 0.002 (2) Å] and forms dihedral angles of 4.8 (1) and 39.0 (1)°, respectively, with the benzene rings attached to the N and C atoms. The acenapthylene ring system is approximately planar [maximum deviation = 0.058 (2) Å] and forms dihedral angles of 85.9 (1) and 48.5 (1)°, respectively, with the pyrollothiazole and chromene ring systems. The molecular conformation is stabilized by three weak intramolecular C-H...O hydrogen bonds, which generate one S(8) and two S(6) ring motifs. In the crystal, pairs of C-H...O hydrogen bonds link centrosymmetrically related molecules into dimers, generating R22(14) ring motifs. The crystal packing also features pairs of C-H...[pi] interactions, which link the dimers into a supramolecular chain along the b axis.

Related literature

For the biological properties 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, 437, 209-214.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]), and for asymmetry parameters, see: Duax et al. (1976[Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. L. Allinger, pp. 271-383. New York: John Wiley.]). For related structures, see: Wei et al. (2012[Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1265-o1266.]); Jagadeesan et al. (2013[Jagadeesan, G., Sethusankar, K., Kathirvelan, D., Haribabu, J. & Reddy, B. S. R. (2013). Acta Cryst. E69, o317.]). For hydrogen-bond motifs, 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
  • C40H29N3O3S

  • Mr = 631.72

  • Triclinic, [P \overline 1]

  • a = 9.9924 (6) Å

  • b = 13.2317 (8) Å

  • c = 13.2867 (8) Å

  • [alpha] = 116.900 (3)°

  • [beta] = 92.325 (2)°

  • [gamma] = 98.518 (3)°

  • V = 1537.79 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 293 K

  • 0.23 × 0.21 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.966, Tmax = 0.976

  • 36242 measured reflections

  • 9612 independent reflections

  • 6569 reflections with I > 2[sigma](I)

  • Rint = 0.029

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

  • wR(F2) = 0.154

  • S = 1.03

  • 9612 reflections

  • 424 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C23-C28 benzene ring.

D-H...A D-H H...A D...A D-H...A
C7-H7...O3 0.93 2.47 3.207 (2) 136
C29-H29A...O3 0.97 2.45 3.074 (2) 122
C17-H17...O3 0.98 2.52 3.091 (2) 117
C38-H38...O1i 0.93 2.40 3.226 (2) 148
C1-H1...Cgii 0.93 2.94 3.713 (3) 142
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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: TK5201 ).


Acknowledgements

The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Duax, W. L., Weeks, C. M. & Rohrer, D. C. (1976). Topics in Stereochemistry, Vol. 9, edited by E. L. Eliel & N. L. Allinger, pp. 271-383. New York: John Wiley.
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, 437, 209-214.  [ISI] [CrossRef] [PubMed] [ChemPort]
Jagadeesan, G., Sethusankar, K., Kathirvelan, D., Haribabu, J. & Reddy, B. S. R. (2013). Acta Cryst. E69, o317.  [CSD] [CrossRef] [details]
Kilonda, A., Compernolle, F. & Hoornaert, G. J. (1995). J. Org. Chem. 60, 5820-5824.  [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Wei, A. C., Ali, M. A., Choon, T. S., Arshad, S. & Razak, I. A. (2012). Acta Cryst. E68, o1265-o1266.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o493-o494   [ doi:10.1107/S1600536813005825 ]

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