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

H C Devarajegowda; K Mahesh Kumar; S Seenivasa; H K Arunkashi; O Kotresh

doi:10.1107/S1600536812051847

. 2013 Jan 9;69(Pt 2):o192. doi: 10.1107/S1600536812051847

(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, O Kotresh ^b

PMCID: PMC3569253 PMID: 23424476

Abstract

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—H⋯S hydrogen bond occurs. In the crystal, C—H⋯O hydrogen bonds generate R ₂ ²(8) rings and π–π 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,
a = 7.0026 (5) Å
b = 7.9939 (6) Å
c = 14.8033 (11) Å
α = 75.433 (4)°
β = 86.642 (4)°
γ = 78.355 (4)°
V = 785.49 (10) Å³
Z = 2
Mo Kα radiation
μ = 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 > 2σ(I)
R _int = 0.024

Refinement

R[F ² > 2σ(F ²)] = 0.027
wR(F ²) = 0.073
S = 1.06
2725 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.15 e Å⁻³

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 Material

Click here for additional data file.^{(18.2KB, cif)}

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812051847/gw2129sup1.cif

e-69-0o192-sup1.cif^{(18.2KB, cif)}

Click here for additional data file.^{(131KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812051847/gw2129Isup2.hkl

e-69-0o192-Isup2.hkl^{(131KB, hkl)}

Click here for additional data file.^{(6.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812051847/gw2129Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O6ⁱ	0.93	2.55	3.4582 (19)	166
C17—H17B⋯O3ⁱⁱ	0.96	2.57	3.386 (2)	143
C18—H18B⋯S2	0.97	2.55	3.1527 (14)	120

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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.

supplementary crystallographic information

Comment

As part of our ongoing studies of coumarins (or 2H-chromen-2-ones) with possible biological activities (Kumar et al., 2012), we now describe the structure of (6-methoxy-2-oxo-2H-chromen-4-yl) methyl morpholine-4-carbodithioate.

The asymmetric unit of (6-methoxy-2-oxo-2H-chromen-4-yl)methyl morpholine-4-carbodithioate is shown in Fig. 1. The 2H-chromene ring system (O3/C8–C16) is essentially planar, with a maximum deviation of 0.070 (1) Å for atom C8 and the morpholine ring adopts a chair conformation: the bond-angle sum for its N7 atom is 357.9 Å. The dihedral angle between the 2H-chromene (O3/C8–C16) ring and the morpholine (N7/O5/C20–C23) ring is 89.09 (6)°. In the crystal structure, (Fig. 2), intermolecular C14—H14···O6 and C17B—H17B···O3 and intramolecular C18—H18B···S2 hydrogen bonds observed and also π–π interactions between fused benzene Cg₍₃₎ (C11–C16) rings of chromene [shortest centroid–centroid distance = 3.5487 (8) Å] further stabilize the crystal packing

Experimental

This compound was prepared according to the reported method (Kumar et al., 2012). Colourless needles of the title compound were grown from a mixed solution of EtOH / CHCl₃(V/V = 1/1) by slow evaporation at room temperature. Colour: yellowish. Yield= 84%, m.p.481 K.