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 Feb 1;74(Pt 2):203-211. doi: 10.1107/S2053229618000657. Epub 2018 Jan 23.
Six closely related N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]arylamides have been synthesized and structurally characterized, together with a representative reaction intermediate. In each of N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]benzamide, CHClNOS, (I), N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]-4-phenylbenzamide, CHClNOS, (II), and 2-bromo-N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]benzamide, CHBrClNOS, (III), the molecules are disordered over two sets of atomic sites, with occupancies of 0.894 (8) and 0.106 (8) in (I), 0.832 (5) and 0.168 (5) in (II), and 0.7006 (12) and 0.2994 (12) in (III). In each of N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]-2-iodobenzamide, CHClINOS, (IV), and N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]-2-methoxybenzamide, CHClNOS, (V), the molecules are fully ordered, but in N-[3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl]-2,6-difluorobenzamide, CHClFNOS, (VI), which crystallizes with Z' = 2 in the space group C2/c, one of the two independent molecules is fully ordered, while the other is disordered over two sets of atomic sites having occupancies of 0.916 (3) and 0.084 (3). All of the molecules in compounds (I)-(VI) exhibit an intramolecular N-H...O hydrogen bond. The molecules of (I) and (VI) are linked by C-H...O hydrogen bonds to form finite zero-dimensional dimers, which are cyclic in (I) and acyclic in (VI), those of (III) are linked by C-H...π(arene) hydrogen bonds to form simple chains, and those of (IV) and (V) are linked into different types of chains of rings, built in each case from a combination of C-H...O and C-H...π(arene) hydrogen bonds. Two C-H...O hydrogen bonds link the molecules of (II) into sheets containing three types of ring. In benzotriazol-1-yl 3,4-dimethoxybenzoate, CHNO, (VII), the benzoate component is planar and makes a dihedral angle of 84.51 (6)° with the benzotriazole unit. Comparisons are made with related compounds.
已合成了六种密切相关的N-[3-(2-氯苯甲酰基)-5-乙基噻吩-2-基]芳基酰胺，并对其进行了结构表征，同时还表征了一种代表性的反应中间体。在N-[3-(2-氯苯甲酰基)-5-乙基噻吩-2-基]苯甲酰胺（CHClNOS，(I)）、N-[3-(2-氯苯甲酰基)-5-乙基噻吩-2-基]-4-苯基苯甲酰胺（CHClNOS，(II)）和2-溴-N-[3-(2-氯苯甲酰基)-5-乙基噻吩-2-基]苯甲酰胺（CHBrClNOS，(III)）中，分子在两组原子位置上无序排列，在(I)中占有率分别为0.894 (8)和0.106 (8)，在(II)中为0.832 (5)和0.168 (5)，在(III)中为0.7006 (12)和0.2994 (12)。在N-[3-(2-氯苯甲酰基)-5-乙基噻吩-2-基]-2-碘苯甲酰胺（CHClINOS，(IV)）和N-[3-(2-氯苯甲酰基)-5-乙基噻吩-2-基]-2-甲氧基苯甲酰胺（CHClNOS，(V)）中，分子完全有序，但在N-[3-(2-氯苯甲酰基)-5-乙基噻吩-2-基]-2,6-二氟苯甲酰胺（CHClFNOS，(VI)）中，其在空间群C2/c中以Z' = 2结晶，两个独立分子中的一个完全有序，而另一个在两组原子位置上无序排列，占有率分别为0.916 (3)和0.084 (3)。化合物(I)-(VI)中的所有分子都表现出分子内N-H...O氢键。(I)和(VI)的分子通过C-H...O氢键相连形成有限的零维二聚体，在(I)中为环状，在(VI)中为非环状，(III)的分子通过C-H...π(芳烃)氢键相连形成简单链，(IV)和(V)的分子连接成不同类型的环链，每种情况都是由C-H...O和C-H...π(芳烃)氢键组合而成。两个C-H...O氢键将(II)的分子连接成片层，该片层包含三种类型的环。在苯并三唑-1-基3,4-二甲氧基苯甲酸酯（CHNO，(VII)）中，苯甲酸酯部分是平面的，与苯并三唑单元的二面角为84.51 (6)°。并与相关化合物进行了比较。
