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Volume 69 
Part 12 
Pages o1849-o1850  
December 2013  

Received 31 October 2013
Accepted 14 November 2013
Online 30 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.053
wR = 0.155
Data-to-parameter ratio = 13.1
Details
Open access

(3aR,8bR)-3a,8b-Dihy­droxy-1-(4-meth­oxy­phen­yl)-2-methyl­sulfan­yl-3-nitro-1,8b-di­hydro­indeno­[1,2-b]pyrrol-4(3aH)-one

aDepartment of Physics, The Madura College, Madurai 625 011, India,bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

In the title compound, C19H16N2O6S, the pyrrolidine ring adopts a twisted conformation with puckering parameters q2 = 0.088 (3) Å and [Phi]2 = 61.5 (14)°. The cyclo­pentane ring adopts a twisted conformation with puckering parameters q2 = 0.099 (2) Å and [Phi]2 = 242.8 (14)°. A weak intra­molecular O-H...O inter­action occurs. In the crystal, pairs of C-H...O inter­actions generate dimers with graph-set motif R22(24) and they are interconnected by pairs of O-H...O hydrogen bonds, which link the mol­ecules into inversion dimers with graph-set motif R22(10).

Related literature

For the importance of pyrrolidine derivatives, see: Cordell (1981[Cordell, G. A. (1981). In Introduction to Alkaloids: A Biogenetic Approach. New York: Wiley International.]); Morais et al. (2009[Morais, C., Gobe, G., Johnson, D. W. & Healy, H. (2009). Angiogenesis, 12, 365-379.]); Bello et al. (2010[Bello, C., Cea, M., Dal Bello, G., Garuti, A., Rocco, I., Cirmena, G., Moran, E., Nahimana, A., Duchosal, M. A., Fruscione, F., Pronzato, P., Grossi, F., Patrone, F., Ballestrero, A., Dupuis, M., Sordat, B., Nencioni, A. & Vogel, P. (2010). Bioorg. Med. Chem. 18, 3320-3334.]); Obniska et al. (2010[Obniska, J., Kopytko, M., Zagórska, A., Chlebek, I. & Kaminski, K. (2010). Arch. Pharm. (Weinheim), 343, 333-341.]). For related structures, see: Liu et al. (2008[Liu, P., Liu, Z., Wang, X.-W. & Wang, W. (2008). Acta Cryst. E64, o1406.]); Ghorbani (2012[Ghorbani, M. H. (2012). Acta Cryst. E68, o2605.]). For additional conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C19H16N2O6S

  • Mr = 400.40

  • Monoclinic, P 21 /n

  • a = 13.6601 (7) Å

  • b = 8.5782 (5) Å

  • c = 15.2373 (8) Å

  • [beta] = 97.684 (3)°

  • V = 1769.46 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.23 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

  • 13771 measured reflections

  • 3311 independent reflections

  • 2661 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.053

  • wR(F2) = 0.155

  • S = 1.02

  • 3311 reflections

  • 253 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3...O5 0.82 2.50 3.014 (3) 122
O3-H3...O1i 0.82 2.06 2.821 (2) 155
C11-H11...O6ii 0.93 2.60 3.461 (3) 155
Symmetry codes: (i) -x+2, -y, -z+1; (ii) -x+1, -y+1, -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: ZQ2211 ).


Acknowledgements

JS and RAN thank the management of the Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (No. SR/FT/CS-073/2009)

References

Bello, C., Cea, M., Dal Bello, G., Garuti, A., Rocco, I., Cirmena, G., Moran, E., Nahimana, A., Duchosal, M. A., Fruscione, F., Pronzato, P., Grossi, F., Patrone, F., Ballestrero, A., Dupuis, M., Sordat, B., Nencioni, A. & Vogel, P. (2010). Bioorg. Med. Chem. 18, 3320-3334.  [CrossRef] [ChemPort] [PubMed]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.
Cordell, G. A. (1981). In Introduction to Alkaloids: A Biogenetic Approach. New York: Wiley International.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Ghorbani, M. H. (2012). Acta Cryst. E68, o2605.  [CSD] [CrossRef] [IUCr Journals]
Liu, P., Liu, Z., Wang, X.-W. & Wang, W. (2008). Acta Cryst. E64, o1406.  [CrossRef] [IUCr Journals]
Morais, C., Gobe, G., Johnson, D. W. & Healy, H. (2009). Angiogenesis, 12, 365-379.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Obniska, J., Kopytko, M., Zagórska, A., Chlebek, I. & Kaminski, K. (2010). Arch. Pharm. (Weinheim), 343, 333-341.  [CrossRef] [ChemPort] [PubMed]
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]


Acta Cryst (2013). E69, o1849-o1850   [ doi:10.1107/S1600536813031279 ]

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