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Volume 69 
Part 9 
Page o1382  
September 2013  

Received 14 July 2013
Accepted 27 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.109
Data-to-parameter ratio = 13.7
Details
Open access

2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl pyrrolidine-1-carbodithioate

aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, and bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

There are two independent molecules in the asymmetric unit of the title compound, C16H15NO3S2, in which the pyrrolidine rings adopt envelope conformations, with a methylene C atom as the flap. The dihedral angles betweeen the near-planar 2H-chromene ring systems [maximum deviations = 0.0167 (20) and 0.0136 (19) Å] and the pyrrolidine rings (all atoms) are 83.83 (11) and 82.43 (11)°. In the crystal, inversion dimers linked by pairs of C-H...O hydrogen bonds occur for one of the molecules. Further C-H...O links involving both molecules generate a three-dimensional network.

Related literature

For a related structure and the synthesis of the title compound, see: Mahabaleshwaraiah et al. (2012[Mahabaleshwaraiah, N. M., Kumar, K. M., Kotresh, O., Al-eryani, W. F. A. & Devarajegowda, H. C. (2012). Acta Cryst. E68, o1566.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15NO3S2

  • Mr = 333.41

  • Triclinic, [P \overline 1]

  • a = 9.7158 (2) Å

  • b = 12.5040 (2) Å

  • c = 13.5925 (2) Å

  • [alpha] = 106.415 (1)°

  • [beta] = 100.882 (1)°

  • [gamma] = 94.854 (1)°

  • V = 1538.74 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.36 mm-1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 21575 measured reflections

  • 5420 independent reflections

  • 4477 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.109

  • S = 1.09

  • 5420 reflections

  • 397 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9A-H9A...O5Bi 0.93 2.48 3.307 (2) 149
C15A-H15A...O5Bi 0.93 2.50 3.319 (3) 147
C9B-H9B...O5Ai 0.93 2.46 3.288 (3) 149
C15B-H15B...O5Ai 0.93 2.50 3.319 (3) 146
C17B-H17B...O3Bii 0.97 2.47 3.432 (3) 170
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+1, -z+2.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, 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.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7109 ).


Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the CCD X-ray facilities, the X-ray data collection and the GCMS, IR, CHNS and NMR data. KMM is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison,Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Mahabaleshwaraiah, N. M., Kumar, K. M., Kotresh, O., Al-eryani, W. F. A. & Devarajegowda, H. C. (2012). Acta Cryst. E68, o1566.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1382  [ doi:10.1107/S1600536813020965 ]

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