Sagar Belakavadi K, Yathirajan Hemmige S, Rathore Ravindranath S, Glidewell Christopher
Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysuru 570 006, India.
Centre for Biological Sciences (Bioinformatics), School of Earth, Biological and Environmental Sciences, Central University of South Bihar, Patna 800 014, India.
Acta Crystallogr C Struct Chem. 2018 Jan 1;74(Pt 1):45-53. doi: 10.1107/S2053229617017326.
Four closely related N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamides, bearing different substituents on the benzamide ring, have been synthesized and structurally characterized. In each of N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-3-fluorobenzamide, CHFNOS, (I), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-4-chlorobenzamide, CHClNOS, (II), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2,6-difluorobenzamide, CHFNOS, (III), and N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)-2-methoxybenzamide, CHNOS, (IV), the last of which crystallizes with Z' = 2 in the space group P-1, the fused six-membered ring adopts a half-chair conformation. In each of (I)-(III), this ring is disordered over two sets of atomic sites having occupancies of 0.811 (6) and 0.189 (6) in (I), 0.645 (7) and 0.355 (7) in (II), and 0.784 (6) and 0.216 (6) in (III), such that the two disorder components of the ring are almost enantiomeric. Molecules of (I) are linked into chains by π-π stacking interactions, and those of (II) are linked into chains by a C-H...π hydrogen bond. A combination of two C-H...O hydrogen bonds and two C-H...π hydrogen bonds links the molecules of (III) into complex sheets, but the molecules of (IV) are linked by a combination of two hydrogen bonds, one each of the C-H...O and C-H...π types, to form centrosymmetric tetramers. The structures of (I)-(IV) are compared with that of the unsubstituted analogue N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophen-2-yl)benzamide and a new refinement of the parent amine 2-amino-3-benzoyl-4,5,6,7-tetrahydrobenzo[b]thiophene, using the original data set, has found that here too the fused six-membered ring exhibits conformational disorder, with occupancies of 0.887 (9) and 0.113 (9). Comparisons are made with some related compounds.
已合成并对四种紧密相关的N-(3-苯甲酰基-4,5,6,7-四氢苯并[b]噻吩-2-基)苯甲酰胺进行了结构表征，这些苯甲酰胺环上带有不同的取代基。在N-(3-苯甲酰基-4,5,6,7-四氢苯并[b]噻吩-2-基)-3-氟苯甲酰胺（CHFNOS，(I)）、N-(3-苯甲酰基-4,5,6,7-四氢苯并[b]噻吩-2-基)-4-氯苯甲酰胺（CHClNOS，(II)）、N-(3-苯甲酰基-4,5,6,7-四氢苯并[b]噻吩-2-基)-2,6-二氟苯甲酰胺（CHFNOS，(III)）和N-(3-苯甲酰基-4,5,6,7-四氢苯并[b]噻吩-2-基)-2-甲氧基苯甲酰胺（CHNOS，(IV)）中，其中最后一种在空间群P-1中以Z' = 2结晶，稠合的六元环呈半椅式构象。在(I) - (III)中，该环在两组原子位置上无序，在(I)中占有率分别为0.811 (6)和0.189 (6)，在(II)中为0.645 (7)和0.355 (7)，在(III)中为0.784 (6)和0.216 (6)，使得环的两个无序组分几乎呈对映体关系。(I)的分子通过π-π堆积相互作用连接成链，(II)的分子通过C-H...π氢键连接成链。两个C-H...O氢键和两个C-H...π氢键的组合将(III)的分子连接成复杂的片层，但(IV)的分子通过两个氢键（一个C-H...O型和一个C-H...π型）的组合连接形成中心对称的四聚体。将(I) - (IV)的结构与未取代类似物N-(3-苯甲酰基-4,5,6,7-四氢苯并[b]噻吩-2-基)苯甲酰胺的结构进行了比较，并且使用原始数据集对母体胺2-氨基-3-苯甲酰基-4,5,6,7-四氢苯并[b]噻吩进行了新的精修，发现此处稠合的六元环也表现出构象无序，占有率分别为0.887 (9)和0.113 (9)。还与一些相关化合物进行了比较。
