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Volume 68 
Part 11 
Page o3167  
November 2012  

Received 11 October 2012
Accepted 13 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.034
wR = 0.082
Data-to-parameter ratio = 13.2
Details
Open access

(3-Oxo-3H-benzo[f]chromen-1-yl)methyl piperidine-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, C20H19N O2S2,the 3Hbenzo-chromene ring system is nearly planar, with a maximum deviation of 0.036 (2) Å, and the piperidine ring adopts a chair conformation: the bond-angle sum for its N atom is 358.7°. The dihedral angle between the 3H-benzo[f]chromene ring and the piperidine ring is 89.07 (8)°. In the crystal, C-H...O hydrogen bonds lead to [010] C(6) chains and weak aromatic [pi]-[pi] interactions between the fused pyran ring and fused benzene ring of benzochromene [centroid-centroid distance = 3.652 (1) Å] are also observed.

Related literature

For a related structure, background to coumarins and details of 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
  • C20H19NO2S2

  • Mr = 369.48

  • Monoclinic, P 21 /c

  • a = 12.4508 (3) Å

  • b = 10.1924 (3) Å

  • c = 14.0188 (4) Å

  • [beta] = 100.953 (2)°

  • V = 1746.63 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.32 mm-1

  • T = 296 K

  • 0.24 × 0.20 × 0.12 mm

Data collection
  • Bruker SMART CCD 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

  • 12000 measured reflections

  • 2993 independent reflections

  • 2380 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.082

  • S = 1.06

  • 2993 reflections

  • 226 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C11-H11...O4i 0.93 2.56 3.308 (2) 138
Symmetry code: (i) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6973 ).


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

References

Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
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] [details]
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3167  [ doi:10.1107/S1600536812042870 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.