Suchetan P A, Naveen S, Lokanath N K, Srivishnu K S, Supriya G M, Lakshmikantha H N
Department of Chemistry, University College of Science, Tumkur University, Tumkur 572 103, India.
Institution of Excellence, University of Mysore, Manasagangotri, Mysuru-6, India.
Acta Crystallogr E Crystallogr Commun. 2016 Mar 31;72(Pt 4):575-82. doi: 10.1107/S2056989016005089. eCollection 2016 Apr 1.
The crystal structures of three N-aryl-sulfonyl-4-fluoro-benzamides, namely 4-fluoro-N-(2-methyl-phenyl-sulfon-yl)benzamide, C14H12FNO3S, (I), N-(2-chloro-phenyl-sulfon-yl)-4-fluorobenzamide, C13H9ClFNO3S, (II), and N-(4-chloro-phenyl-sulfon-yl)-4-fluoro-benzamide monohydrate, C13H9ClFNO3S·H2O, (III), are described and compared with related structures. The asymmetric unit of (I) contains two independent mol-ecules (A and B), while that of (II) contains just one mol-ecule, and that of (III) contains a mol-ecule of water in addition to one main mol-ecule. The dihedral angle between the benzene rings is 82.83 (11)° in mol-ecule A and 85.01 (10)° in mol-ecule B of (I), compared to 89.91 (10)° in (II) and 81.82 (11)° in (III). The crystal structure of (I) features strong N-H⋯O hydrogen bonds between the A and B mol-ecules, resulting in an R 4 (4)(16) tetra-meric unit. These tetra-meric units are connected into sheets in the bc plane by various C-H⋯O inter-actions, and adjacent sheets are further inter-linked via C-H⋯πar-yl inter-actions, forming a three-dimensional architecture. The crystal structure is further stabilized by πar-yl-πar-yl and S=O⋯πar-yl inter-actions. In the crystal of (II), mol-ecules are connected into R 2 (2)(8) and R 2 (2)(14) dimers via N-H⋯O hydrogen bonds and C-H⋯O inter-actions, respectively; the dimers are further inter-connected via a weak C=O⋯πar-yl inter-action, leading to the formation of chains along [1-10]. In the crystal of (III), N-H⋯O and O-H⋯O hydrogen bonds involving both the main mol-ecule and the solvent water mol-ecule results in the formation of sheets parallel to the bc plane. The sheets are further connected by C-H⋯O inter-actions and weak C-Cl⋯πar-yl, C-F⋯πar-yl and S=O⋯πar-yl inter-actions, forming a three-dimensional architecture.
描述了三种N-芳基磺酰基-4-氟苯甲酰胺的晶体结构，即4-氟-N-(2-甲基苯基磺酰基)苯甲酰胺，C₁₄H₁₂FNO₃S，(I)；N-(2-氯苯基磺酰基)-4-氟苯甲酰胺，C₁₃H₉ClFNO₃S，(II)；以及N-(4-氯苯基磺酰基)-4-氟苯甲酰胺一水合物，C₁₃H₉ClFNO₃S·H₂O，(III)，并与相关结构进行了比较。(I)的不对称单元包含两个独立分子(A和B)，(II)的不对称单元仅包含一个分子，(III)的不对称单元除一个主要分子外还包含一个水分子。(I)中分子A的苯环之间的二面角为82.83 (11)°，分子B的为85.01 (10)°，而(II)中为89.91 (10)°，(III)中为81.82 (11)°。(I)的晶体结构特征是A和B分子之间存在强N-H⋯O氢键，形成一个R₄(4)(16)四聚体单元。这些四聚体单元通过各种C-H⋯O相互作用在bc平面上连接成片，相邻的片层通过C-H⋯π芳基相互作用进一步相互连接，形成三维结构。晶体结构通过π芳基-π芳基和S=O⋯π芳基相互作用进一步稳定。在(II)的晶体中，分子分别通过N-H⋯O氢键和C-H⋯O相互作用连接成R₂(2)(8)和R₂(2)(14)二聚体；这些二聚体通过弱C=O⋯π芳基相互作用进一步相互连接，导致沿[1-10]方向形成链。在(III)的晶体中，涉及主要分子和溶剂水分子的N-H⋯O和O-H⋯O氢键导致形成与bc平面平行的片层。这些片层通过C-H⋯O相互作用以及弱C-Cl⋯π芳基、C-F⋯π芳基和S=O⋯π芳基相互作用进一步连接，形成三维结构。
