(3-Oxo-3H-benzo[f]chromen-1-yl)methyl piperidine-1-carbodithio­ate

Kotresh, O.; Kumar, K.M.; Mahabaleshwaraiah, N.M.; Arunkashi, H.K.; Devarajegowda, H.C.

doi:10.1107/S1600536812042870

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 (C-C) = 0.003 Å
R = 0.034
wR = 0.082
Data-to-parameter ratio = 13.2
Details

(3-Oxo-3H-benzo[f]chromen-1-yl)methyl piperidine-1-carbodithioate

O. Kotresh,^a K. Mahesh Kumar,^a N. M. Mahabaleshwaraiah,^a H. K. Arunkashi ^b and H. C. Devarajegowda ^b ^*

^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-HO 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).

Experimental

Crystal data

C₂₀H₁₉NO₂S₂
M_r = 369.48
Monoclinic, P 2₁ /c
a = 12.4508 (3) Å
b = 10.1924 (3) Å
c = 14.0188 (4) Å
= 100.953 (2)°
V = 1746.63 (8) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.770, T_max = 1.000
12000 measured reflections
2993 independent reflections
2380 reflections with I > 2(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.082
S = 1.06
2993 reflections
226 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11O4ⁱ	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); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); 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.
Kumar, K. M., Kour, D., Kapoor, K., Mahabaleshwaraiah, N. M., Kotresh, O., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o878-o879.
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin,USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds