Shakuntala K, Naveen S, Lokanath N K, Suchetan P A
Department of Chemistry, Sri Bhuvanendra College, Karkala 574 104, India.
Institution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India.
Acta Crystallogr E Crystallogr Commun. 2017 Apr 11;73(Pt 5):673-677. doi: 10.1107/S2056989017005230. eCollection 2017 May 1.
The crystal structures of three isomeric compounds of formula CHClNOS, namely 3,5-di-chloro--(2,3-di-methyl-phen-yl)-benzene-sulfonamide (I), 3,5-di-chloro--(2,6-di-methyl-phen-yl)benzene-sulfonamide (II) and 3,5-di-chloro--(3,5-di-methyl-phen-yl)benzene-sulfonamide (III) are described. The mol-ecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3 (6)° in (I), 42.1 (2)° in (II) and 54.4 (3)° in (III). The mol-ecular conformation of (II) is stabilized by intra-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The crystal structure of (I) features N-H⋯O hydrogen-bonded (8) loops inter-connected (7) chains of C-H⋯O inter-actions, forming a three-dimensional architecture. The structure also features π-π inter-actions [⋯ = 3.6970 (14) Å]. In (II), N-H⋯O hydrogen-bonded (8) loops are inter-connected π-π inter-actions [inter-centroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to the axis. In (III), adjacent (4) chains of N-H⋯O hydrogen-bonded mol-ecules running parallel to [010] are connected C-H⋯π inter-actions, forming sheets parallel to the plane. Neighbouring sheets are linked offset π-π inter-actions [inter-centroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.
描述了分子式为CHClNOS的三种同分异构体化合物的晶体结构,即3,5-二氯-N-(2,3-二甲基苯基)苯磺酰胺(I)、3,5-二氯-N-(2,6-二甲基苯基)苯磺酰胺(II)和3,5-二氯-N-(3,5-二甲基苯基)苯磺酰胺(III)。这三种化合物的分子均呈U形,两个芳环在(I)中的倾斜角度为41.3 (6)°,在(II)中为42.1 (2)°,在(III)中为54.4 (3)°。(II)的分子构象通过分子内C-H⋯O氢键和C-H⋯π相互作用得以稳定。(I)的晶体结构具有由N-H⋯O氢键连接的(8)环,这些环相互连接形成(7)条C-H⋯O相互作用链,构成三维结构。该结构还具有π-π相互作用[⋯ = 3.6970 (14) Å]。在(II)中,N-H⋯O氢键连接的(8)环通过π-π相互作用[质心间距 = 3.606 (3) Å]相互连接,形成平行于c轴的一维结构。在(III)中,平行于[010]的相邻(4)条由N-H⋯O氢键连接的分子链通过C-H⋯π相互作用相连,形成平行于bc平面的片层。相邻片层通过错位π-π相互作用[质心间距 = 3.8303 (16) Å]相连,形成三维结构。