1233 ISSN 1063-7745, Crystallography Reports, 2021, Vol. 66, No. 7, pp. 1233–1237. © Pleiades Publishing, Inc., 2021. Synthesis and Crystal Structure Analysis of 3,3'-[(3-Sulfanyl Phenyl)Methylene]Bis(4-Hydroxy-2H-1-Benzopyran-2-One) : 5-Methyl-1,3-Thiazol-2(3H)-Imine G. Sharma a , S. Anthal a , M. B. Deshmukh b , P. P. Mohire b , T. R. Bhosale b , C. Sudarsanakumar c , and R. Kant a, * a X-ray Crystallography Laboratory, Department of Physics, University of Jammu, Jammu Tawi, 180006 India b Department of Chemistry, Shivaji University, Kolhapur, 416004 India c School of Pure and Applied Physics, Mahatma Gandhi University, Kottayam, 686560 Kerala * e-mail: rkant.ju@gmail.com Received August 29, 2020; revised March 31, 2021; accepted March 31, 2021 Abstract—The structure of 3,3'-[(3-sulfanylphenyl)methylene]bis(4-hydroxy-2H-1-benzopyran-2-one) : 5-methyl-1,3-thiazol-2(3H)-imine was determined by X-ray crystallography. It crystallizes in the mono- clinic crystal system with space group Cc. The unit cell parameters are: a = 20.1008(12) Å, b = 15.2487(9) Å, c = 8.3462(4) Å, β = 92.86(2)°, and Z = 4. The crystal structure has been solved by using direct methods and refined by full matrix least squares procedures to a final R-factor of 0.040 (wR(F 2 ) = 0.097) for 5152 observed reflections. The bond angles around the chromene moieties are almost identical but deviate significantly from the values observed in some analogous structures. There exists few C–H⋅⋅⋅O/O–H⋅⋅⋅O intramolecular hydro- gen interactions, besides intermolecular interactions of the type N–H⋅⋅⋅O, S–H⋅⋅⋅N, O–H⋅⋅⋅N, and C–H⋅⋅⋅S, respectively. DOI: 10.1134/S1063774521070166 INTRODUCTION Chromene derivatives are important intermediates in various naturally occurring substances such as alka- loids, anthocyanins, polyphenols, tocopherols and flavonoids [1]. Many substituted 2-aminochromene derivatives have been utilized in cosmetic and pigment industry [2]. Lonchocarpin is another natural chromene with yellow orange crystals which is isolated from the ether extract of seeds and roots of Lonchocar- pus scericeus [3]. Fused chromene scaffolds have also several relevance’s in heterocyclic chemistry field [4] such as anticancer [5–9], anti-tuberculotic [10], anti- microbial [11], anti-inflammatory [12], antioxidant [13], analgesic [14], antimalarial [15], and anti-HIV [16] activities. The 2H-chromene nucleus also present in health promoting agents like polyphenols [17] and are a favoured scaffold found in many biologically active molecules [18–20]. 4-Hydroxy benzopyran 2-one acts as an anticoagulant for the treatment of thrombo- embolic conditions. The anticoagulant activity of bis- benzopyran results from inhibition of a vitamin K- dependent step in the hepatic synthesis of clotting fac- tors II (prothrombin). The presence of thiazole moiety enhances the fibrinogen receptor antagonists with antithrombotic activity [21]. Therefore, the synthesis and structural characterization of the title compound was undertaken. EXPERIMENTAL Synthesis A mixture of 4-hydroxycoumarin (1 mmol) and 3-mercapto benzaldehyde (1 mmol), with 5 mL LTTM was taken in a 50 mL round bottomed flask and srirred at room temperature to get Knoevenagel prod- uct, monitored by TLC and then 2-amino 5-methyl 1,3-thiazole (1 mmol) were added and the same reac- tion mixture further ref luxed for 20 min. The progress of the reaction was monitored by TLC using petro- leum ether –ethyl acetate (8 : 2 ) then cooled to room temperature. The solid product formed was col- lected by simple filtration, washed with ethanol and diethyl ether. Finally, the crude product was recrystal- lized from ethanol to obtain the pure crystalline prod- uct. Yield: 55%, m.p.: 206°C. The reaction scheme of the compound is shown in Fig. 1. Yield, 55%, m.p. 206°C; IR (v max ) cm –1 : 3400– 3300 (SH), 3250 (NH), 2920 (C–H), 1668 (C=O), 1604 (C=C); 1 H NMR (DMSO-d 6 ) : δ (ppm) 2.15 (3H, s, CH 3 ), 4.8 (1H, s, NH of thiazole ring), 6.2 (1H, s, CH benzylic proton), 6.8–8.1 (13H, m, aromatic protons v/v STRUCTURE OF ORGANIC COMPOUNDS