3-Anilinothio­carbonyl-4-hydroxy­chromen-2-one

Rajni Kant; Lovely Sarmal; Sabeta Kohli; Kamni; Mehtab Parveen

doi:10.1107/S1600536809011246

. 2009 Mar 31;65(Pt 4):o938. doi: 10.1107/S1600536809011246

3-Anilinothiocarbonyl-4-hydroxychromen-2-one

Rajni Kant ^a,^*, Lovely Sarmal ^a, Sabeta Kohli ^a, Kamni ^b, Mehtab Parveen ^c

PMCID: PMC2969103 PMID: 21582638

Abstract

The geometrical parameters of the title compound, C₁₆H₁₁NO₃S, are in the usual ranges. The two aromatic residues are not coplanar and are twisted by a dihedral angle of 66.63 (6)°. The crystal structure is stabilized by N—H⋯O and O—H⋯S interactions.

Related literature

For literature on coumarins, see: Campbell (1959 ▶); Murray et al. (1982 ▶); Wolska et al. (1990 ▶); Harvey (1999 ▶); Matern et al. (1999 ▶); Yang et al. (1992 ▶); Tsai et al. (2000 ▶).

Experimental

Crystal data

C₁₆H₁₁NO₃S
M _r = 297.33
Monoclinic,
a = 14.8059 (9) Å
b = 5.5245 (4) Å
c = 17.4438 (12) Å
β = 109.091 (7)°
V = 1348.34 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 293 K
0.30 × 0.24 × 0.18 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: none
11450 measured reflections
4408 independent reflections
2320 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.134
S = 1.01
4408 reflections
235 parameters
All H-atom parameters refined
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: CrysAlisPro (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlisPro; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011246/jh2075sup1.cif

e-65-0o938-sup1.cif^{(15.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011246/jh2075Isup2.hkl

e-65-0o938-Isup2.hkl^{(211.6KB, hkl)}

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
N1—H1A⋯O2	0.96 (2)	1.77 (2)	2.5923 (19)	141 (2)
O3—H3A⋯S1	1.05 (2)	1.81 (3)	2.8163 (15)	159 (2)

Open in a new tab

Acknowledgments

The authors are thankful to the Department of Science and Technology of the Government of India for funding under research project SR/S2/CMP-47/2003.

supplementary crystallographic information

Comment

Coumarins belong to a group of compounds known as benzopyrones, all of which consist of a benzene ring joined to a pyrone moiety.

Coumarins are found to have a wide spectrum of biological activity, e.g. antithronbotic effect, vascodilating effect on vessel, tonic influence on capillary blood vessels, reduction of blood pressure, antispastic and photosensitizing effect (Wolska et al., 1990).

Interestingly, coumarins exhibit inhibitory effect on DNA gyrase, which may be linked to anti-HIV (human immuno deficiency virus) activity (Matern et al., 1999).

Coumarins are also found to exhibit anti-malarial activity (Yang et al., 1992).

Recently Collinin, isolated from Zathoxylum Schinifolium, has been found to exhibit anti-HBV (hepatitis B virus) activity (Tsai et al., 2000).

Owing to the general importance of these coumarin analogues we report herein the synthesis and crystal structure of a new coumarin 3-anilinothiocarbonyl-4-hydroxychromen-2-one, (I).

The geometrical parameters (i.e. bond distances and angles) of (I) are in the usual ranges. The two aromatic residues are not coplanar and are twisted by a dihedral angle of 66.63 (6)°. The crystal structure is stabilized by X—H···A interactions.

Experimental

Scheme1: The mixture of 4-hydroxy coumarin, phenylisothiocyanate was taken in THF.The base Na₂CO₃ was also added to it. The reaction mixture was refluxed on water bath for three hours. Progress of the reaction was monitored by TLC. After completion the reaction mixture was poured into water and worked up with ether and then in ethyl acetate. The ether layer showed the presence of three compounds from which the title compound (I) was separated by column chromatography followed by crystallization from chloroform-methanol as white crystalline solid. Melting point: 421–423 K.