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Volume 69 
Part 11 
Page o1683  
November 2013  

Received 14 October 2013
Accepted 16 October 2013
Online 23 October 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.109
Data-to-parameter ratio = 20.5
Details
Open access

(6-Meth­oxy-2-oxo-2H-chromen-4-yl)methyl piperidine-1-carbodi­thio­ate

aDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India,bDepartment of Physics, Sri D Devaraja Urs Govt. First Grade College, Hunsur 571 105, Mysore District, Karnataka, India, and cDepartment 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, C17H19NO3S2, the maximum deviation of atoms in the 2H-chromene ring system is 0.0097 (14) Å and the piperidine ring adopts a chair conformation. The dihedral angle between the 2H-chromene ring and the piperidine ring (all atoms) is 87.59 (8)°. In the crystal, inversion dimers linked by pairs of C-H...O inter­actions generate R22(22) loops. Further C-H...O hydrogen bonds link the dimers into [110] chains and weak aromatic [pi]-[pi] stacking [shortest centroid-centroid distance = 3.824 (8) Å] is also observed.

Related literature

For a related structure and the synthesis, 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
  • C17H19NO3S2

  • Mr = 349.45

  • Triclinic, [P \overline 1]

  • a = 6.9731 (2) Å

  • b = 10.2310 (3) Å

  • c = 11.9955 (3) Å

  • [alpha] = 92.024 (1)°

  • [beta] = 90.176 (1)°

  • [gamma] = 106.497 (1)°

  • V = 819.96 (4) Å3

  • Z = 2

  • 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: multi-scan (SADABS; Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.770, Tmax = 1.000

  • 17441 measured reflections

  • 4261 independent reflections

  • 3513 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.109

  • S = 1.04

  • 4261 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.28 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
C19-H19B...O5i 0.97 2.50 3.410 (2) 157
C23-H23A...O3ii 0.97 2.60 3.365 (2) 136
Symmetry codes: (i) -x, -y, -z+1; (ii) x-1, y-1, z.

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: HB7152 ).


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. KMK is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities.

References

Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1683  [ doi:10.1107/S1600536813028432 ]

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