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Six new 1-aroyl-4-(4-methoxyphenyl)piperazines have been prepared, using coupling reactions between benzoic acids and N-(4-methoxyphenyl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-methoxyphenyl)piperazine, C18H20N2O2, (I). The molecules of 1-(2-fluorobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19FN2O2, (II), are linked by two C--H···O hydrogen bonds to form chains of rings, which are linked into sheets by an aromatic π-π stacking interaction. 1-(2-Chlorobenzoyl)-4-(4-methoxyphenyl) piperazine, C18H19ClN2O2, (III), 1-(2-bromobenzoyl)-4-(4-methoxyphenyl) piperazine, C18H19BrN2O2, (IV), and 1-(2-iodobenzoyl)-4-(4-methoxyphenyl) piperazine, C18H19IN2O2, (V), are isomorphous, but in (III) the aroyl ring is disordered over two sets of atomic sites having occupancies of 0.942 (2) and 0.058 (2). In each of (III)-(V), a combination of two C--H···π(arene) hydrogen bonds links the molecules into sheets. A single O--H···O hydrogen bond links the molecules of 1-(2-hydroxybenzoyl)-4-(4-methoxyphenyl) piperazine, C18H20N2O3, (VI), into simple chains. Comparisons are made with the structures of some related compounds. [ABSTRACT FROM AUTHOR]

In the title compound, C61H15ClN2O3, the heterocyclic ring adopts an envelope conformation, folded across the N⋯N line, with the 2,5-di­meth­oxy­phenyl unit occupying a quasi-axial site. There are two N—H⋯O hydrogen bonds in the structure: one hydrogen bond links mol­ecules related by a 41 screw axis to form a C(6) chain, and the other links inversion-related pairs of mol­ecules to form an R2²(8) ring. The ring motif links all of the chains into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds. [ABSTRACT FROM AUTHOR]

In each of the compounds 1-[(1,3-benzodioxol-5-yl)methyl]-4-(3-fluorobenzoyl)-piperazine, C19H19FN2O3 (I), 1-[(1,3-benzodioxol-5-yl)methyl]-4-(2,6-difluorobenzoyl) piperazine, C19H18F2N2O3 (II), and 1-[(1,3-benzodioxol-5-yl)methyl]-4-(2,4-dichlorobenzoyl)piperazine, C19H19Cl2N2O3 (III), the piperazine rings adopt a chair conformation with the (1,3-benzodioxol-5-yl)methyl substituent occupying an equatorial site: the five-membered rings are all slightly folded across the O...O line leading to envelope conformations. The dihedral angle between the planar amidic fragment and the haloaryl ring is 62.97 (5)° in (I) but 77.72 (12)° and 75.50 (5)° in (II) and (III), respectively. Despite their similarity in constitution and conformation, the supramolecular interactions in (I)-(III) differ: in (I), a combination of C--H...O and C--H...π(arene) hydrogen bonds links the molecules into a three-dimensional framework structure, but there are no hydrogen bonds of any sort in either (II) or (III), although the structure of (III) contains a short Cl...Cl contact between inversion-related pairs of molecules. [ABSTRACT FROM AUTHOR]

The syntheses and structures of five molecular salts of protonated 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine (C11H19N2S+) with different deprotonated carboxylic acids (4-methylbenzoic acid, 4-bromobenzoic acid, 3,5-dinitrobenzoic acid, fumaric acid and succinic acid) are reported, namely 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 4-methylbenzoate, C11H19N2S+·C8H7O2 -, (I), 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 4-bromobenzoate, C11H19N2S+·-C7H4BrO2 -, (II), 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium 3,5-dinitrobenzoate, C11H19N2S+·C7H3N2O6 -, (III), bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) fumarate, 2C11H19N2S+·C4H2O4 2-,(IV), and the 1:1 co-crystal of bis(2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium) succinate and 2-amino-4,4,7,7-tetramethyl-4,5,6,7-tetrahydro-1,3-benzothiazol-3-ium hydrogen succinate 4,4,7,7-tetramethyl-3a,5,6,7a-tetrahydrobenzothiazol-2-ylamine, 1.5C11H19N2S+·0.5C4H4O4 2-·0.5C4H5O4 -. 0.5C11H18N2S, (V). In every case, the cation protonation occurs at the N atom of the thiazole ring and the sixmembered ring adopts a half-chair conformation (in some cases, the deviating methylene groups are disordered over two sets of sites). The C--N bond lengths of the nominal -NH+＝C--NH2 fragment of the cation are indistinguishable, indicating a significant contribution of the -NH--C＝N+H2 resonance form to the structure. The packing for (I)-(V) features a robust local R2 ²(8) loop motif in which the cation forms two near-linear N--H...O hydrogen bonds from the N+--H group and syn H atom of the amine group to the carboxylate group of an adjacent anion [(V) shows disorder of one of these bonds over N--H...O and N...H--O contributors but the same R2 2(8) loop results for both disorder components]. The anti H atom of the -NH2 group also forms an N--H...O hydrogen bond, which results in [001] chains in (I) and (II), isolated centrosymmetric tetramers in (III) and [100] chains in (IV) and (V). Hirshfeld fingerprint plots and contact percentages for the different types of contacts of the cations are discussed. [ABSTRACT FROM AUTHOR]

In the molecule of the title compound, C15H14N2O2, the 2-ethylphenyl group is disordered over two sets of atomic sites having occupancies of 0.515 (19) and 0.485 (19), and the dihedral angle between the two partial-occupancy aryl rings is 6(2)°. A combination of C--H...O hydrogen bonds and nitroπ ...(arene) interactions links the molecules into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds [ABSTRACT FROM AUTHOR]

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, C20H16ClNO2S, (I), N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]‐4‐phenylbenzamide, C26H20ClNO2S, (II), and 2‐bromo‐N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]benzamide, C20H15BrClNO2S, (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, C20H15ClINO2S, (IV), and N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]‐2‐methoxybenzamide, C21H18ClNO3S, (V), the molecules are fully ordered, but in N‐[3‐(2‐chlorobenzoyl)‐5‐ethylthiophen‐2‐yl]‐2,6‐difluorobenzamide, C20H14ClF2NO2S, (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, C15H13N3O4, (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. [ABSTRACT FROM AUTHOR]

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, C22H18FNO2S, (I), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[ b]thiophen-2-yl)-4-chlorobenzamide, C22H18ClNO2S, (II), N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[ b]thiophen-2-yl)-2,6-difluorobenzamide, C22H17F2NO2S, (III), and N-(3-benzoyl-4,5,6,7-tetrahydrobenzo[ b]thiophen-2-yl)-2-methoxybenzamide, C23H21NO3S, (IV), the last of which crystallizes with Z′ = 2 in the space group P, 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. [ABSTRACT FROM AUTHOR]

In each of 1-(4-fluorophenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1 H-pyrazolo[4,3- c]pyridine, C21H19F4N3O2S, (I), 1-(4-chlorophenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1 H-pyrazolo[4,3- c]pyridine, C21H19ClF3N3O2S, (II), and 1-(3-methylphenyl)-5-methylsulfonyl-3-[4-(trifluoromethyl)phenyl]-4,5,6,7-tetrahydro-1 H-pyrazolo[4,3- c]pyridine, C22H22F3N3O2S, (III), the reduced pyridine ring adopts a half-chair conformation with the methylsulfonyl substituent occupying an equatorial site. Although compounds (I) and (II) are not isostructural, having the space groups Pbca and P212121, respectively, their molecular conformations are very similar, but the conformation of compound (III) differs from those of (I) and (II) in the relative orientation of the N-benzyl and methylsulfonyl substituents. In compounds (II) and (III), but not in (I), the trifluoromethyl groups are disordered over two sets of atomic sites. Molecules of (I) are linked into centrosymmetric dimers by C-H...π(arene) hydrogen bonds, molecules of (II) are linked by two C-H...O hydrogen bonds to form ribbons of R33(18) rings, which are themselves further linked by a C-Cl...π(arene) interaction, and a combination of C-H...O and C-H...π(arene) hydrogen bonds links the molecules of (III) into sheets. Comparisons are made with the structures of some related compounds. [ABSTRACT FROM AUTHOR]

Six new 1-aroyl-4-(4-meth-oxy-phen-yl)piperazines have been prepared, using coupling reactions between benzoic acids and N -(4-meth-oxy-phen-yl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-meth-oxy-phen-yl)piperazine, C 18 H 20 N 2 O 2 , (I). The mol-ecules of 1-(2-fluoro-benzo-yl)-4-(4-meth-oxy-phen-yl)piperazine, C 18 H 19 FN 2 O 2 , (II), are linked by two C-H⋯O hydrogen bonds to form chains of rings, which are linked into sheets by an aromatic π-π stacking inter-action. 1-(2-Chloro-benzo-yl)-4-(4-meth-oxy-phen-yl)piperazine, C 18 H 19 ClN 2 O 2 , (III), 1-(2-bromo-benzo-yl)-4-(4-meth-oxy-phen-yl)piperazine, C 18 H 19 BrN 2 O 2 , (IV), and 1-(2-iodo-benzo-yl)-4-(4-meth-oxyphen-yl)piperazine, C 18 H 19 IN 2 O 2 , (V), are isomorphous, but in (III) the aroyl ring is disordered over two sets of atomic sites having occupancies of 0.942 (2) and 0.058 (2). In each of (III)-(V), a combination of two C-H⋯π(arene) hydrogen bonds links the mol-ecules into sheets. A single O-H⋯O hydrogen bond links the mol-ecules of 1-(2-hy-droxy-benzo-yl)-4-(4-meth-oxy-phen-yl)piperazine, C 18 H 20 N 2 O 3 , (VI), into simple chains. Comparisons are made with the structures of some related compounds.

In the title compound, C 61 H 15 ClN 2 O 3 , the heterocyclic ring adopts an envelope conformation, folded across the N⋯N line, with the 2,5-di-meth-oxy-phenyl unit occupying a quasi-axial site. There are two N-H⋯O hydrogen bonds in the structure: one hydrogen bond links mol-ecules related by a 4 1 screw axis to form a C (6) chain, and the other links inversion-related pairs of mol-ecules to form an R 2 2 (8) ring. The ring motif links all of the chains into a continuous three-dimensional framework structure. Comparisons are made with the structures of some related compounds.

In both 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3- benzo-thia-zol-3-ium benzoate, C 11 H 19 N 2 S + ·C 7 H 5 O 2 - , (I), and 2-amino-4,4,7,7-tetra-methyl-4,5,6,7-tetra-hydro-1,3-benzo-thia-zol-3-ium picrate (2,4,6-tri-nitro-phenolate), C 11 H 19 N 2 S + ·C 6 H 2 N 3 O 7 - , (II), the cations are conformationally chiral as the six-membered rings adopt half-chair conformations, which are disordered over two sets of atomic sites giving approximately enanti-omeric disorder. For both cations, the bond lengths indicate delocalization of the positive charge comparable to that in an amidinium cation. The bond lengths in the picrate anion in (II) are consistent with extensive delocalization of the negative charge into the ring and onto the nitro groups, in two of which the O atoms are disordered over two sets of sites. In (I), the ionic components are linked by N-H⋯O hydrogen bonds to form a chain of rings, and in (II), the N-H⋯O hydrogen bonds link the components into centrosymmetric four-ion aggregates containing seven hydrogen bonded rings of four different types.

In the title compound, C15H12N4O4, the dihedral angle between the heterocyclic rings is 12.60 (8)°, and that between the benzene ring and the adjacent heterocyclic ring is 85.14 (6)°. In the crystal, a combination of N-H⋯O and O-H⋯O hydrogen bonds link mol-ecules related by a glide plane into a C(5) C(6)[R (2) 2(9)] chain of rings, which is a distinctly different packing motif to those observed in hydrated modifications of this compound.