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The reaction of 1-amino­anthraquinone with 7,7′,8,8′-tetra­cyano­quinodimethane yielded the title charge-transfer complex, C14H9NO2·C12H4N4. The mol­ecules have maximum deviations from the mean planes through the non-H atoms of 0.0769 (14) Å for an oxo O atom and 0.1175 (17) Å for a cyano N atom, respectively. The dihedral angle between the two planes is 3.55 (3)°. In the crystal, mol­ecules are stacked into columns along the a-axis direction. Pairs of N—H...N and N—H...O inter­actions connect the mol­ecules perpendicular to the stacking direction. Additionally, an intra­molecular N—H...O hydrogen-bond inter­action is observed for 1-amino­anthraquinone.

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In the title compound, C10H11N3O2S, the 1,3-benzodioxole and hydrazinecarbothio­amide fragments are nearly planar [(mean deviations from planarity for non-H atoms of 0.0325 (12) Å and 0.0707 (10) Å, respectively] and subtend a dihedral angle of 29.06 (5)°. In the crystal, mol­ecules are linked by pairs of almost linear N—H...S hydrogen bonds, forming inversion dimers. These dimers are additionally connected by weaker and strongly bent N—H...S inter­actions into chains along [101]. There is one additional weak N—H...O contact which, if considered as an inter­action, leads to the formation of a three-dimensional network.

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In the title compound, C15H11BrN4OS, the least-squares plane through the 5-bromo­isatin fragment forms a dihedral angle of 13.63 (14)° with the phenyl ring. The mol­ecular conformation features intra­molecular N—H...N and N—H...O hydrogen bonds. In the crystal, mol­ecules are connected via pairs of N—H...O inter­actions into centrosymmetric dimers. Additionally, π–π stacking inter­actions link mol­ecules into chains parallel to the a axis with short C...C distances being observed between the phenyl and thio­carbonyl [3.236 (8) Å] groups and between the thio­carbonyl and carbonyl [3.351 (4) Å] groups of stacked mol­ecules.

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In the title compound, C9H11N3S, there is an intra­molecular O—H...O hydrogen bond involving the OH group and the adjacent methoxy O atom. The mol­ecule is essentially planar, with the maximum deviation from the mean plane of the non-H atoms being 0.1127 (14) Å for the methyl C atom. In the crystal, mol­ecules are connected via centrosymmetric pairs of N—H...S and O—H...O hydrogen bonds into a two-dimensional network parallel to (10-3).
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