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Volume 69 
Part 8 
Pages o1345-o1346  
August 2013  

Received 10 May 2013
Accepted 20 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.104
Data-to-parameter ratio = 14.4
Details
Open access

1''-Allyl-5''-(4-methoxybenzylidene)-7'-(4-methoxyphenyl)-1',3',5',6',7',7a'-hexahydrodispiro[acenaphthylene-1,5'-pyrrolo[1,2-c][1,3]thiazole-6',3''-piperidine]-2,4''(1H)-dione

aDepartment of Chemistry, College of Sciences, King Saud University, PO Box 2455, Riyadh 11451, Saudi Arabia, and bDepartment of Physics, The Madura College, Madurai 625 011, India
Correspondence e-mail: ambujasureshj@yahoo.com

In the title compound, C39H36N2O4S, the piperidine ring adopts a twisted half-chair conformation. In the pyrrolothiazole fused-ring system, the pyrrole ring adopts an envelope conformation (with the C atom bound to the thiazole ring being the flap atom) and the thiazole ring also exhibits an envelope conformation (with the N atom bound to the pyrrole ring as the flap). The molecular structure features a weak intramolecular C-H...O interaction. In the crystal, a C-H...O interaction forms a linear chain along the diagonal of the ac plane, generating a C(14) graph-set motif. A weak C-H...[pi] interaction also occurs.

Related literature

For the importance of hetrocyclic rings, see: Guengerich et al. (1973[Guengerich, F. P., DiMari, S. J. & Broquist, H. P. (1973). J. Am. Chem. Soc. 95, 2055-2056.]); Lalezari & Schwartz (1988[Lalezari, I. & Schwartz, E. L. (1988). J. Med. Chem. 31, 1427-1429.]); Tsuge & Kanemasa (1989[Tsuge, O. & Kanemasa, S. (1989). Advances in Heterocyclic Chemistry, edited by A. R. Katritzky, Vol. 45, p. 231. San Diego: Academic Press.]); Puder et al. (2000[Puder, C., Krastel, P. & Zeeck, A. (2000). J. Nat. Prod. 63, 1258-1260.]); Nair & Suja (2007[Nair, V. & Suja, T. D. (2007). Tetrahedron, 63, 12247-12275.]). For related acenaphthylene structures, see: Suresh et al. (2011[Suresh, J., Vishnupriya, R., Kumar, R. R., Sivakumar, S. & Lakshman, P. L. N. (2011). Acta Cryst. E67, o3210.]). For additional conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). 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
  • C39H36N2O4S

  • Mr = 628.76

  • Monoclinic, P 21 /n

  • a = 11.3956 (7) Å

  • b = 20.1346 (12) Å

  • c = 14.3860 (8) Å

  • [beta] = 103.153 (1)°

  • V = 3214.2 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 293 K

  • 0.21 × 0.19 × 0.18 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.974

  • 26225 measured reflections

  • 5979 independent reflections

  • 4873 reflections with I > 2[sigma](I)

  • Rint = 0.024

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.104

  • S = 1.07

  • 5979 reflections

  • 415 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C52-C57 ring.

D-H...A D-H H...A D...A D-H...A
C2-H2B...O3 0.97 2.45 2.9587 (19) 113
C93-H93...O1i 0.93 2.49 3.343 (2) 153
C58-H58B...Cg1ii 0.96 2.85 3.487 (2) 125
Symmetry codes: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) -x+1, -y, -z+1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). 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: GW2135 ).


Acknowledgements

This project was supported by the Research Center, Deanship of Scientific Research, College of Science, King Saud University.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Guengerich, F. P., DiMari, S. J. & Broquist, H. P. (1973). J. Am. Chem. Soc. 95, 2055-2056.  [CrossRef] [ChemPort] [Web of Science]
Lalezari, I. & Schwartz, E. L. (1988). J. Med. Chem. 31, 1427-1429.  [CrossRef] [ChemPort] [PubMed] [Web of Science]
Nair, V. & Suja, T. D. (2007). Tetrahedron, 63, 12247-12275.  [Web of Science] [CrossRef] [ChemPort]
Puder, C., Krastel, P. & Zeeck, A. (2000). J. Nat. Prod. 63, 1258-1260.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
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]
Suresh, J., Vishnupriya, R., Kumar, R. R., Sivakumar, S. & Lakshman, P. L. N. (2011). Acta Cryst. E67, o3210.  [CSD] [CrossRef] [IUCr Journals]
Tsuge, O. & Kanemasa, S. (1989). Advances in Heterocyclic Chemistry, edited by A. R. Katritzky, Vol. 45, p. 231. San Diego: Academic Press.


Acta Cryst (2013). E69, o1345-o1346   [ doi:10.1107/S1600536813020084 ]

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