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Six 1-halobenzoyl-4-(2-meth-oxy-phen-yl)piperazines having Z' values of one, two or four; disorder, pseudosymmetry, twinning and supra-molecular assembly in one, two or three dimensions.

ABSTRACT: Six 1-halobenzoyl-4-(2-meth-oxy-phen-yl)piperazines have been prepared using carbodi-imide-mediated coupling reactions between halo-benzoic acids and N-(2-meth-oxy-phen-yl)piperazine. The mol-ecules of 1-(4-fluoro-benzo-yl)-4-(2-meth-oxy-phen-yl)piperazine, C₁₈H₁₉FN₂O₂ (I), are linked into a chain of rings by a combination of C-H?O and C-H??(arene) hydrogen bonds. 1-(4-Chloro-benzo-yl)-4-(2-meth-oxy-phen-yl)piperazine, C₁₈H₁₉ClN₂O₂ (II), crystallizes in the space group Pca2₁ with Z' = 4 and it exhibits both pseudosymmetry and inversion twinning: a combination of six C-H?O and two C-H??(arene) hydrogen bonds generate a three-dimensional assembly. In 1-(4-bromo-benzo-yl)-4-(2-meth-oxy-phen-yl)piperazine, C₁₈H₁₉BrN₂O₂ (III), which also crystallizes in space group Pca2₁ but with Z' = 2, the bromo-benzoyl unit in one of the mol-ecules is disordered. Pseudosymmetry and inversion twinning are again present, and a combination of three C-H?O and one C-H??(arene) hydrogen bonds generate a two-dimensional assembly. A single C-H?O hydrogen bond links the mol-ecules of 1-(4-iodo-benzo-yl)-4-(2-meth-oxy-phen-yl)piperazine, C₁₈H₁₉IN₂O₂ (IV), into simple chains but in the isomeric 3-iodo-benzoyl analogue (V), which crystallizes in space group P2₁2₁2₁ with Z' = 2, a two-dimensional assembly is generated by a combination of four C-H?O and two C-H??(arene) hydrogen bonds; pseudosymmetry and inversion twinning are again present. A single C-H?O hydrogen bond links the mol-ecules of 1-(2-fluoro-benzo-yl)-4-(2-meth-oxy-phen-yl)piperazine, C₁₈H₁₉FN₂O₂ (VI), into simple chains. Comparisons are made with the structures of some related compounds.

SUBMITTER: Harish Chinthal C

PROVIDER: S-EPMC7784055 | biostudies-literature | 2021 Jan

REPOSITORIES: biostudies-literature

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Six 1-halobenzoyl-4-(2-meth-oxy-phen-yl)piperazines having Z' values of one, two or four; disorder, pseudosymmetry, twinning and supra-molecular assembly in one, two or three dimensions.

Harish Chinthal Chayanna C Kavitha Channappa N CN Yathirajan Hemmige S HS Foro Sabine S Glidewell Christopher C

Acta crystallographica. Section E, Crystallographic communications 20210101 Pt 1

Six 1-halobenzoyl-4-(2-meth-oxy-phen-yl)piperazines have been prepared using carbodi-imide-mediated coupling reactions between halo-benzoic acids and N-(2-meth-oxy-phen-yl)piperazine. The mol-ecules of 1-(4-fluoro-benzo-yl)-4-(2-meth-oxy-phen-yl)piperazine, C18H19FN2O2 (I), are linked into a chain of rings by a combination of C-H⋯O and C-H⋯π(arene) hydrogen bonds. 1-(4-Chloro-benzo-yl)-4-(2-meth-oxy-phen-yl)piperazine, C18H19</su ...[more]

PMID: 33520274

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Project description:Twelve 4-(4-meth-oxy-phen-yl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. The monohydrated benzoate, 4-fluoro-benzoate, 4-chloro-benzoate and 4-bromo-benzoate salts, C11H17N2O+·C7H5O2 -·H2O (I), C11H17N2O+·C7H4FO2 -·H2O (II), C11H17N2O+·C7H4ClO2 -·H2O (III), and C11H17N2O+·C7H4BrO2 -·H2O (IV), respectively, are isomorphous and all exhibit disorder in the 4-meth-oxy-phenyl unit: the components are linked by N-H⋯O and O-H⋯O hydrogen bond to form chains of rings. The unsolvated 2-hy-droxy-benzoate, pyridine-3-carboxyl-ate and 2-hy-droxy-3,5-di-nitro-benzoate salts, C11H17N2O+·C7H5O3 - (V), C11H17N2O+·C6H4NO2 - (VI) and C11H17N2O+·C7H3N2O7 - (VII), respectively, are all fully ordered: the components of (V) are linked by multiple N-H⋯O hydrogen bonds to form a chain of rings; those of (VI) are linked into a three-dimensional framework by a combination of N-H⋯O, C-H⋯O and C-H⋯N hydrogen bonds and those of (VII), where the anion has a structure reminiscent of the picrate anion, are linked into a three-dimensional array by N-H⋯O and C-H⋯O hydrogen bonds. The hydrogensuccinate and hydrogenfumarate salts, C11H17N2O+·C4H5O4 - (VIII) and C11H17N2O+·C4H3O3 - (IX), respectively, are isomorphous, and both exhibit disorder in the anionic component: N-H⋯O and O-H⋯O hydrogen bonds link the ions into sheets, which are further linked by C-H⋯π(arene) inter-actions. The anion of the hydrogenmaleate salt, C11H17N2O+·C4H3O3 - (X), contains a very short and nearly symmetrical O⋯H⋯O hydrogen bond, and N-H⋯O hydrogen bonds link the anions into chains of rings. The ions in the tri-chloro-acetate salt, C11H17N2O+·C2Cl3O2 - (XI), are linked into simple chains by N-H⋯O hydrogen bonds. In the hydrated chloranilate salt, 2C11H17N2O+·C6Cl2O4 2-·2H2O (XII), which crystallizes as a non-merohedral twin, the anion lies across a centre of inversion in space group P21/n, and a combination of N-H⋯O and O-H⋯O hydrogen bonds generates complex sheets. Comparisons are made with the structures of some related compounds.

Project description:Fifteen 4-(2-meth-oxy-phen-yl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. In the isostructural 4-chloro-benzoate and 4-bromo-benzoate salts, C11H17N2O+·C7H4ClO2 - (I) and C11H17N2O+·C7H4BrO2 - (II), and the 4-iodo-benzoate salt C11H17N2O+·C7H4IO2 - (III), the ions are linked by N-H⋯O hydrogen bonds, forming centrosymmetric R 4 4(12) four-ion aggregates; a similar aggregate is formed in the 2-chloro-benzoate salt (V), isomeric with (I). In the 2-fluoro-benzoate salt C11H17N2O+·C7H4FO2 - (IV), and the isomorphous pair of salts, the 2-bromo-benzoate (VI), isomeric with (II) and 2-iodo-benzoate (VII), isomeric with (III), N-H⋯O and C-H⋯π(arene) interactions link the components into three-dimensional arrays. Four-ion R 4 4(12) aggregates are also found in the 2-methyl-benzoate, 4-amino-benzoate and 4-nitro-benzoate salts, C11H17N2O+·C8H7O2 - (VIII), C11H17N2O+·C7H6NO2 - (IX) and C11H17N2O+·C7H4NO4 - (X), but those in (IX) are linked into complex sheets by an additional N-H⋯O hydrogen bond. In the 3,5-dinitrobenzoate salt, C11H17N2O+·C7H3N2O6 -·2H2O (XI), N-H⋯O and O-H⋯O hydrogen bonds link the components into a complex ribbon structure. In the picrate salt, C11H17N2O+·C6H2N3O7 - (XII), the four-ion aggregates are linked into chains of rings by C-H⋯O hydrogen bonds. In the hydrogen maleate salt, C11H17N2O+·C4H3O4 - (XIII), two- and three-centre hydrogen bonds link the ions into a ribbon structure while both anions contain very short but asymmetric O-H⋯O hydrogen bonds, having O⋯O distances of 2.4447 (16) and 2.4707 (17) Å. O-H⋯O Hydrogen bonds link the anions in the hydrogen fumarate salt (XIV), isomeric with (XIII), into chains that are linked into sheets via N-H⋯O hydrogen bonds. In the hydrogen (2R,3R)-tartrate salt, C11H17N2O+·C4H5O6 -·1.698H2O (XV), the anions are linked into sheets by O-H⋯O hydrogen bonds. Comparisons are made with the structures of some related compounds.

Dataset Information

Six 1-halobenzoyl-4-(2-meth-oxy-phen-yl)piperazines having Z' values of one, two or four; disorder, pseudosymmetry, twinning and supra-molecular assembly in one, two or three dimensions.

Publications

Six 1-halobenzoyl-4-(2-meth-oxy-phen-yl)piperazines having <i>Z</i>' values of one, two or four; disorder, pseudosymmetry, twinning and supra-molecular assembly in one, two or three dimensions.

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