Yennawar Hemant P, Tierney John, Hullihen Patrick D, Silverberg Lee J
Department of Chemistry, Pennsylvania State University, University Park, PA 16802, USA.
Pennsylvania State University, Brandywine Campus, 312 M Main Building, 25, Yearsley Mill Rd, Media, PA 19063, USA.
Acta Crystallogr E Crystallogr Commun. 2015 Feb 11;71(Pt 3):264-7. doi: 10.1107/S2056989015001954. eCollection 2015 Mar 1.
In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thia-zolidine ring is attached to two chloro-phenyl rings. The chloro-phenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) is trans to the chloro-phenyl ring on the 2-carbon. The chloro-phenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thia-zolidine ring has a twisted conformation on the S-Cmethine bond in (1), and an envelope conformation with the S atom 0.715 (3) Å out of the plane of other four atoms in (2). In the crystal of (1), mol-ecules are linked by C-H⋯O hydrogen bonds, as well as by slipped parallel π-π inter-actions [inter-centroid distance = 3.840 (3) Å] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), mol-ecules are linked via C-H⋯O and C-H⋯Cl hydrogen bonds, forming slabs parallel to (001).
在标题化合物C15H11Cl2NOS（1）和C15H11Cl2NO2S（2）的晶体结构中，其中（2）是（1）的氧化形式，噻唑烷环连接到两个氯苯环上。2-碳原子位置上的氯苯环与（1）中S原子的方向相同，而在（2）中，S原子指向相反方向。（2）中手性S原子上的O原子与2-碳上的氯苯环呈反式。每个结构中的氯苯环平面接近正交，在（1）和（2）中的二面角分别为78.61（6）°和87.46（8）°。（1）中噻唑烷环在S-C次甲基键上具有扭曲构象，（2）中噻唑烷环具有信封式构象，S原子偏离其他四个原子平面0.715（3）Å。在（1）的晶体中，分子通过C-H⋯O氢键以及通过反演相关苯环之间的滑移平行π-π相互作用[质心间距 = 3.840（3）Å]相连，形成平行于（001）的片层。在（2）的晶体中，分子通过C-H⋯O和C-H⋯Cl氢键相连，形成平行于（001）的平板。
