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

Devarajegowda, H.C.; Kumar, K.M.; Seenivasa, S.; Arunkashi, H.K.; Kotresh, O.

doi:10.1107/S1600536812051847

Volume 69
Part 2
Page o192
February 2013

Received 2 November 2012
Accepted 25 December 2012
Online 9 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.027
wR = 0.073
Data-to-parameter ratio = 13.1
Details

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

H. C. Devarajegowda,^a ^* K. Mahesh Kumar,^b S. Seenivasa,^c H. K. Arunkashi ^a and O. Kotresh ^b

^aDepartment of Physics, Yuvaraja's College (Constituent College), University of Mysore, Mysore 570 005, Karnataka, India,^bDepartment of Chemistry, Karnatak University's Karnatak Science College, Dharwad, Karnataka 580 001, India, and ^cDeapartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103, Karnataka, India
Correspondence e-mail: devarajegowda@yahoo.com

In the title compound, C₁₆H₁₇NO₄S₂, the 2H-chromene ring system is nearly planar, with a maximum deviation of 0.070 (1) Å, and the morpholine ring adopts a chair conformation; the bond-angle sum for its N atom is 357.9°. The dihedral angle between the the 2H-chromene ring and the best plane through the morpholine ring is 89.09 (6)°. An intramolecular C-HS hydrogen bond occurs. In the crystal, C-HO hydrogen bonds generate R₂²(8) rings and [pi] - [pi] interactions occur between fused benzene rings of the chromene system [shortest centroid-centroid distance = 3.5487 (8) Å].

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

C₁₆H₁₇NO₄S₂
M_r = 351.43
Triclinic, $[P \overline 1]$
a = 7.0026 (5) Å
b = 7.9939 (6) Å
c = 14.8033 (11) Å
= 75.433 (4)°
= 86.642 (4)°
= 78.355 (4)°
V = 785.49 (10) Å³
Z = 2
Mo K radiation
= 0.36 mm^-1
T = 296 K
0.24 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) T_min = 0.770, T_max = 1.000
13583 measured reflections
2725 independent reflections
2482 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.073
S = 1.06
2725 reflections
208 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C14-H14O6ⁱ	0.93	2.55	3.4582 (19)	166
C17-H17BO3ⁱⁱ	0.96	2.57	3.386 (2)	143
C18-H18BS2	0.97	2.55	3.1527 (14)	120
Symmetry codes: (i) -x-1, -y+1, -z+1; (ii) x, y-1, z.

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 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2129 ).

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 (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds