(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithio­ate

Mahabaleshwaraiah, N.M.; Kumar, K.M.; Kotresh, O.; Al-eryani, W.F.A.; Devarajegowda, H.C.

doi:10.1107/S1600536812018004

Volume 68
Part 6
Page o1584
June 2012

Received 21 April 2012
Accepted 23 April 2012
Online 2 May 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.035
wR = 0.099
Data-to-parameter ratio = 14.0
Details

(5,7-Dimethyl-2-oxo-2H-chromen-4-yl)methyl pyrrolidine-1-carbodithioate

N. M. Mahabaleshwaraiah,^a K. Mahesh Kumar,^a O. Kotresh,^a Waleed Fadl Ali Al-eryani ^b and H. C. Devarajegowda ^b ^*

^aDepartment of Chemistry, Karnatak Science College, Dharwad 580 001, Karnataka, 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, C₁₇H₁₉NO₂S₂, the 2H-chromene ring system is almost planar, with a maximum deviation of 0.044 (2) Å, and the pyrrolidine ring adopts an envelope conformation. The dihedral angle between the 2H-chromene system and the planar part of the pyrrolidine ring is 83.65 (8)°. A weak intramolecular C-HS hydrogen bond occurs. The crystal structure features C-HO hydrogen bonds and [pi] - [pi] interactions, with a centroid-centroid distance of 3.5728 (16) Å.

Related literature

For biological properties of coumarins, see: Adavi et al. (2004); Laurin et al. (1999); Kulkarni et al. (2006). For related structures, see: Kumar et al. (2012); Kant et al. (2012). For synthetic details, see: Shastri et al. (2004); Vasilliev & Polackov (2000).

Experimental

Crystal data

C₁₇H₁₉NO₂S₂
M_r = 333.45
Monoclinic, P 2₁ /c
a = 13.7023 (4) Å
b = 15.9082 (4) Å
c = 7.5511 (2) Å
= 103.358 (1)°
V = 1601.45 (7) Å³
Z = 4
Mo K radiation
= 0.34 mm^-1
T = 293 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: scan (SADABS; Sheldrick, 2007) T_min = 0.770, T_max = 1.000
12677 measured reflections
2805 independent reflections
2410 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.099
S = 1.07
2805 reflections
201 parameters
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11BS2	0.97	2.51	3.172 (2)	126
C18-H18O4ⁱ	0.93	2.52	3.411 (3)	161
C22-H22CS1	0.96	2.81	3.564 (2)	137
Symmetry code: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: WN2472 ).

Acknowledgements

The authors acknowledge the Universities Sophisticated Instrumental Centre, Karnatak University, Dharwad, for CCD X-ray facilities, single-crystal X-ray diffractometer, GCMS, IR, CHNS and NMR data. NMM is grateful to Karnatak Science College, Dharwad, for providing laboratory facilities. He is also thankful to P C Jabin Science College, Hubli and UGC for allowing him to do research under FIP.

References

Adavi, H. H., Kusanur, R. A., Kulkarni, M. V. (2004). J. Indian Chem. Soc. 81, 981-986.
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Kant, R., Gupta, V. K., Kapoor, K., Kour, G., Kumar, K. M., Mahabaleshwaraiah, N. M. & Kotresh, O. (2012). Acta Cryst. E68, o1104-o1105.
Kulkarni, M. V., Kulkarni, G. M., Lin, C. H. & Sun, C. M. (2006). Curr. Med. Chem. 13, 2795-2818.
Kumar, K. M., Kour, D., Kapoor, K., Mahabaleshwaraiah, N. M., Kotresh, O., Gupta, V. K. & Kant, R. (2012). Acta Cryst. E68, o878-o879.
Laurin, P., Ferround, D., Schio, L., Klich, M., Hamelin, C. D., Mowais, P., Lassaigne, P., Bonnefoy, A. & Musicki, B. (1999). Bioorg. Med. Chem. Lett. 9, 2875-2877.
Shastri, L. A., Ghate, M. D. & Kulkarni, M. V. (2004). Indian J. Chem. Sect. B, 43, 2416-2422.
Sheldrick, G. M. (2007). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vasilliev, A. N. & Polackov, A. D. (2000). Molecules, 5, 1014-1017.

organic compounds