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Volume 69 
Part 9 
Pages o1431-o1432  
September 2013  

Received 31 July 2013
Accepted 9 August 2013
Online 14 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.091
Data-to-parameter ratio = 15.1
Details
Open access

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

aDepartment of Physics, Y. Y. D. Govt. First Grade College, Belur 573 115, Hassan, Karnataka, India,bDepartment of Physics, AVK College for Women, Hassan 573 201, Karnataka, India,cDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India, and dDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C15H16ClNO2S2, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.023 (2) Å. In the crystal, C-H...O hydrogen bonds give R21(7) motifs, which generate [100] chains. C-H...[pi] and [pi]-[pi] interactions between chromene moieties [shortest ring centroid-centroid distance = 3.6199 (13) Å] consolidate the packing.

Related literature

For biological applications of coumarins and dithiocarbamates, see: Abd Elhafez et al. (2003[Abd Elhafez, O. M., El Khrisy, A. M., Badria, F. & Fathy, A. M. (2003). Arch. Pharm. Res. 26, 686-696.]); Basanagouda et al. (2009[Basanagouda, M., Kulkarni, M. V., Sharma, D., Gupta, V. K., Pranesha, Sandhyarani, P. & Rasal, V. P. (2009). J. Chem. Sci. 121, 485-495.]); Borges et al. (2009[Borges, F., Roleira, F., Milhazes, N., Uriarte, E. & Santana, L. (2009). Front. Med. Chem. 4, 23-85.]); Bottomeley et al. (1985[Bottomeley, P., Hodless, R. A. & Smart, N. A. (1985). Residue Rev. 95, 45-89.]); Emmanuel-Giota et al. (2001[Emmanuel-Giota, A. A., Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2001). J. Heterocycl. Chem. 38, 717-722.]); Hamdi & Dixneuf (2007[Hamdi, N. & Dixneuf, P. H. (2007). In Topics in Heterocyclic Chemistry. Berlin, Heidelberg: Springer-Verlag.]); Marchenko et al. (2006[Marchenko, M. M., Kopyl'chuk, G. P., Shmarakov, I. A., Ketsa, O. V. & Kushnir, V. M. (2006). Pharm. Chem. J. 40, 296-297.]); Teramoto et al. (1980[Teramoto, S., Saito, R. & Shirasu, Y. (1980). Teratology, 21, 71-78.]); Trapkov et al. (1996[Trapkov, V. A., Parfenov, E. A. & Smirnov, L. D. (1996). Pharm. Chem. J. 30, 445-447.]). For a related structure and the synthesis of the title compound, see: Kumar et al. (2012[Kumar, K. M., Kour, D., Kapoor, K., Mahabaleshwaraiah, N. M., Kotresh, O., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o878-o879.]).

[Scheme 1]

Experimental

Crystal data
  • C15H16ClNO2S2

  • Mr = 341.86

  • Monoclinic, P 21 /c

  • a = 7.7005 (2) Å

  • b = 23.3452 (8) Å

  • c = 9.7016 (3) Å

  • [beta] = 110.349 (2)°

  • V = 1635.21 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.49 mm-1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2007[Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 11261 measured reflections

  • 2865 independent reflections

  • 2413 reflections with I > 2[sigma](I)

  • Rint = 0.024

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

  • wR(F2) = 0.091

  • S = 1.08

  • 2865 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C14/C15/C18-C21 ring.

D-H...A D-H H...A D...A D-H...A
C12-H12A...O5i 0.97 2.43 3.264 (3) 144
C18-H18...O5i 0.93 2.54 3.424 (3) 159
C8-H8A...Cg2ii 0.97 2.95 3.792 (3) 146
Symmetry codes: (i) x+1, y, z; (ii) x, y, 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: ZS2274 ).


Acknowledgements

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

References

Abd Elhafez, O. M., El Khrisy, A. M., Badria, F. & Fathy, A. M. (2003). Arch. Pharm. Res. 26, 686-696.  [PubMed] [ChemPort]
Basanagouda, M., Kulkarni, M. V., Sharma, D., Gupta, V. K., Pranesha, Sandhyarani, P. & Rasal, V. P. (2009). J. Chem. Sci. 121, 485-495.  [CSD] [CrossRef] [ChemPort]
Borges, F., Roleira, F., Milhazes, N., Uriarte, E. & Santana, L. (2009). Front. Med. Chem. 4, 23-85.
Bottomeley, P., Hodless, R. A. & Smart, N. A. (1985). Residue Rev. 95, 45-89.  [PubMed]
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Emmanuel-Giota, A. A., Fylaktakidou, K. C., Hadjipavlou-Litina, D. J., Litinas, K. E. & Nicolaides, D. N. (2001). J. Heterocycl. Chem. 38, 717-722.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hamdi, N. & Dixneuf, P. H. (2007). In Topics in Heterocyclic Chemistry. Berlin, Heidelberg: Springer-Verlag.
Kumar, K. M., Kour, D., Kapoor, K., Mahabaleshwaraiah, N. M., Kotresh, O., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o878-o879.  [CSD] [CrossRef] [ChemPort] [details]
Marchenko, M. M., Kopyl'chuk, G. P., Shmarakov, I. A., Ketsa, O. V. & Kushnir, V. M. (2006). Pharm. Chem. J. 40, 296-297.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Teramoto, S., Saito, R. & Shirasu, Y. (1980). Teratology, 21, 71-78.  [CrossRef] [ChemPort] [PubMed] [ISI]
Trapkov, V. A., Parfenov, E. A. & Smirnov, L. D. (1996). Pharm. Chem. J. 30, 445-447.  [CrossRef]


Acta Cryst (2013). E69, o1431-o1432   [ doi:10.1107/S160053681302240X ]

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