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Volume 69 
Part 9 
Page o1454  
September 2013  

Received 2 August 2013
Accepted 5 August 2013
Online 21 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.035
wR = 0.090
Data-to-parameter ratio = 14.2
Details
Open access

2-Oxo-2-(2-oxo-2H-chromen-3-yl)ethyl diethyldithiocarbamate

aDepartment of Physics, Y. Y. D. Govt. First Grade College, Belur 573 115, Hassan, Karnataka, India,bDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India,cDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, and dP. G. Department of Physics, LVD College, Raichur 584 103, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C16H17NO3S2, the dihedral angles between the O/C/C/S group and the 2H-chromene ring system and the thiocarbamate group are 14.46 (9) and 83.30 (9)°, respectively. The bond-angle sum at the N atom is 360.0°. One of the methyl C atoms lies above the thiocarbamate plane and one lies below it [deviations = 1.264 (3) and -1.147 (3) Å, respectively]. In the crystal, inversion dimers linked by pairs of C-H...O hydrogen bonds generate R22(10) loops. Weak aromatic [pi]-[pi] stacking interactions [shortest centroid-centroid distance = 3.8138 (11) Å] are also observed.

Related literature

For backgrond to chromenes, a related structure and the synthesis of the title compound, see: Kumar et al. (2012[Kumar, K. M., Devarajegowda, H. C., Jeyaseelan, S., Mahabaleshwaraiah, N. M. & Kotresh, O. (2012). Acta Cryst. E68, o1657.]).

[Scheme 1]

Experimental

Crystal data
  • C16H17NO3S2

  • Mr = 335.43

  • Orthorhombic, P b c n

  • a = 16.3379 (5) Å

  • b = 9.6445 (3) Å

  • c = 20.5078 (6) Å

  • V = 3231.43 (17) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART CCD diffractometer

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

  • 12047 measured reflections

  • 2831 independent reflections

  • 2129 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.090

  • S = 1.05

  • 2831 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...O5i 0.93 2.49 3.198 (2) 134
Symmetry code: (i) -x, -y+1, -z+1.

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: HB7115 ).


Acknowledgements

The authors thank the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for the X-ray data collection and the GCMS, IR, CHNS and NMR data. KMK thanks 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]
Kumar, K. M., Devarajegowda, H. C., Jeyaseelan, S., Mahabaleshwaraiah, N. M. & Kotresh, O. (2012). Acta Cryst. E68, o1657.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1454  [ doi:10.1107/S1600536813021806 ]

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