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Volume 69 
Part 11 
Pages o1684-o1685  
November 2013  

Received 7 August 2013
Accepted 13 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.031
wR = 0.102
Data-to-parameter ratio = 17.0
Details
Open access

(7-Chloro-2-oxo-2H-chromen-4-yl)methyl 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

In the title compound, C15H14ClNO2S2, the 2H-chromene ring system is essentially planar, with a maximum deviation of 0.0133 (10) Å. Three C atoms and their attached H atoms of the pyrrolidine ring are disordered [occupany ratio 0.874 (7):0.126 (7)] with both disorder components adopting a twisted conformation. The dihedral angle between the 2H-chromene ring system and the major occupancy component of the pyrrolidine ring is 89.45 (7)°. In the crystal, inversion dimers linked by pairs of C-H...S and C-H...O inter­actions generate R22(24) and R22(10) loops, respectively. Further C-H...O hydrogen bonds link the dimers into [100] chains. C-H...[pi] inter­actions also occur and there is very weak [pi]-[pi] stacking [inter­planar spacing = 3.650 (5) Å; centroid-centroid distance = 4.095 (7) Å] between inversion-related chloro­benzene rings.

Related literature

For biological applications of coumarins and di­thio­carbamates, see: Brillon (1992[Brillon, D. (1992). Sulfur Rep. 12, 297-332.]); Burns et al. (2010[Burns, M., Lloyd-Jones, G. C., Moseley, J. D. & Renny, J. S. (2010). J. Org. Chem. 75, 6347-6353.]); Kawaii et al. (2001[Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M. & Yoshizawa, Y. (2001). Anticancer Res. 21, 917-923.]); Khan et al. (2004[Khan, K. M., Saify, Z. S., Khan, M. Z., Zia-Ullah, Choudhary, M. I., Atta-Ur-Rahman, Perveen, S., Chohan, Z. H. & Supuran, C. T. (2004). J. Enzyme Inhib. Med. Chem. 19, 373-379.]); Yu et al. (2003[Yu, D., Suzuki, M., Xie, L., Morris-Natschke, S. L. & Lee, K. H. (2003). Med. Res. Rev. 23, 322-345.]). For details of the synthesis and a related structure with comparison bond lengths, 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
  • C15H14ClNO2S2

  • Mr = 339.84

  • Triclinic, [P \overline 1]

  • a = 7.9073 (2) Å

  • b = 9.2891 (2) Å

  • c = 10.8865 (2) Å

  • [alpha] = 84.474 (1)°

  • [beta] = 79.798 (1)°

  • [gamma] = 72.437 (1)°

  • V = 749.52 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.54 mm-1

  • T = 296 K

  • 0.22 × 0.18 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.]) Tmin = 0.770, Tmax = 1.000

  • 16446 measured reflections

  • 3417 independent reflections

  • 3136 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.031

  • wR(F2) = 0.102

  • S = 1.18

  • 3417 reflections

  • 201 parameters

  • 6 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C7-C12 ring.

D-H...A D-H H...A D...A D-H...A
C9-H9...S3i 0.93 2.87 3.7910 (16) 170
C21-H21B...O5ii 0.97 2.60 3.3434 (19) 134
C16-H16B...Cg4ii 0.97 2.93 3.761 (1) 144
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART 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: 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: PK2494 ).


Acknowledgements

The authors acknowledge the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for CCD X-ray facilities, single-crystal X-ray diffractometer, GCMS, IR, CHNS and NMR data. NMM is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities. He is also thankful to P. C. Jabin Science College, Hubli and UGC for permission to do research under FIP.

References

Brillon, D. (1992). Sulfur Rep. 12, 297-332.  [ChemPort]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burns, M., Lloyd-Jones, G. C., Moseley, J. D. & Renny, J. S. (2010). J. Org. Chem. 75, 6347-6353.  [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kawaii, S., Tomono, Y., Ogawa, K., Sugiura, M., Yano, M. & Yoshizawa, Y. (2001). Anticancer Res. 21, 917-923.  [PubMed] [ChemPort]
Khan, K. M., Saify, Z. S., Khan, M. Z., Zia-Ullah, Choudhary, M. I., Atta-Ur-Rahman, Perveen, S., Chohan, Z. H. & Supuran, C. T. (2004). J. Enzyme Inhib. Med. Chem. 19, 373-379.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Mahabaleshwaraiah, N. M., Kumar, K. M., Kotresh, O., Al-eryani, W. F. A. & Devarajegowda, H. C. (2012). Acta Cryst. E68, o1566.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2007). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Yu, D., Suzuki, M., Xie, L., Morris-Natschke, S. L. & Lee, K. H. (2003). Med. Res. Rev. 23, 322-345.  [Web of Science] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1684-o1685   [ doi:10.1107/S1600536813028080 ]

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