Two N-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1H-1,2,4-triazol-3-yl]methyl}benzamides as disordered ethanol monosolvates

Abstract

<jats:p>Two new <jats:italic>N</jats:italic>-{[4-(3-aryl-4-sydnonylideneamino)-5-sulfanylidene-1<jats:italic>H</jats:italic>-1,2,4-triazol-3-yl]methyl}benzamides have been prepared by acid-promoted condensation reactions between 3-aryl-4-formylsydnones and <jats:italic>N</jats:italic>-[(4-amino-5-sulfanylidene-1<jats:italic>H</jats:italic>-1,2,4-triazol-3-yl)methyl]benzamide, and both have been crystallized as ethanol monosolvates. <jats:italic>N</jats:italic>-{[4-(3-Phenyl-4-sydnonylideneamino)-5-sulfanylidene-1<jats:italic>H</jats:italic>-1,2,4-triazol-3-yl]methyl}benzamide ethanol monosolvate, C<jats:sub>19</jats:sub>H<jats:sub>15</jats:sub>N<jats:sub>7</jats:sub>O<jats:sub>3</jats:sub>S·C<jats:sub>2</jats:sub>H<jats:sub>6</jats:sub>O (<jats:bold>I</jats:bold>), and <jats:italic>N</jats:italic>-({4-[3-(4-methylphenyl)-4-sydnonylideneamino]-5-sulfanylidene-1<jats:italic>H</jats:italic>-1,2,4-triazol-3-yl}methyl)benzamide ethanol monosolvate, C<jats:sub>20</jats:sub>H<jats:sub>17</jats:sub>N<jats:sub>7</jats:sub>O<jats:sub>3</jats:sub>S·C<jats:sub>2</jats:sub>H<jats:sub>6</jats:sub>O (<jats:bold>II</jats:bold>), differ only in the presence of a methyl group for (<jats:bold>II</jats:bold>) instead of a hydrogen atom for (<jats:bold>I</jats:bold>), and in both of them the ethanol component is disordered over two sets of atomic sites having occupancies of 0.836 (6) and 0.164 (6) in (<jats:bold>I</jats:bold>), and 0.906 (6) and 0.094 (6) in (<jats:bold>II</jats:bold>). Combinations of O—H...O and N—H...O hydrogen bonds link the molecules into cyclic, centrosymmetric four-molecule aggregates. Comparisons are made with the structures of some related compounds.</jats:p>