3-(benzo[d]thiazol-2-YL)phenol and 4-(benzo[d]thiazol-2-YL)phenol: Crystal Structure Determination, DFT Calculations and Visualizing Intermolecular Interactions Using Hirshfeld Surface Analysis. (12th April 2016)

• Record Type: Journal Article
• Authors: Mudsainiyan, R. K.; Jassal, A. K.
• Is Part Of: Molecular crystals and liquid crystals. Volume 629(2016)
• Page Start: 120
• Page End: 134
• Publication Date: 2016-04-12
• Subjects: Centrosymmetric -- 2D-fingerprint plot -- hirshfeld surface -- positional isomers -- space group -- two-dimensi-onal framework; Molecular crystals -- Periodicals; Liquid crystals -- Periodicals; Liquid crystals; Molecular crystals; Periodicals; 548
• DOI: 10.1080/15421406.2015.1107812
• Languages: English
• ISSNs: 1542-1406

Abstract

ABSTRACT: This article describes the synthesis and X-ray crystal structure analysis of3-(benzo[ d ]thiazol-2-yl) phenol (I) and 4-(benzo[ d ]thiazol-2-yl)phenol (II), crystallized in centrosymmetric triclinic and orthorhombic space groups respectively. The packing in the unit cell of these two positional isomers are different resulting difference in various types of intermolecular interactions (C-H…S, O-H…Ow and O-H…N) connect the molecules into 2D frameworks. Due to presence of lattice water in compound (I ), H-bonding interactions are strong and melting point of (I ) is comparatively higher than (II ). The DFT optimized molecular geometries in (I ) and (II ) agree closely with those obtained from crystallographic studies. GRAPHICAL ABSTRACT: The compounds(I) and(II) have been crystallized in centrosymmetric space groups. The DFT optimized molecular geometries in both compounds agree closely with those obtained from the crystallographic studies. An interplay of O-H…Ow and O-H…N type strong hydrogen bonds and C-H…S type weak interactions connect the molecules of (I ) and (II ) into 2D framework. Hirshfeld surface analysis of (I ) indicates that the H…H and H…π contacts can account for 47.4% and 18.7%, respectively, of the Hirshfeld surface area, whereas the corresponding fraction in (II ) is 36.5% and 29.5%, respectively.