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In the title salt, C14H16N+·Cl, the complete cation and complete anion are generated by the application of mirror symmetry. The mol­ecule is nonplanar, as seen in the dihedral angle between the terminal phenyl rings [70.92 (5)°]. In the crystal, N—H...Cl hydrogen bonds involving both aza­nium H atoms link the ions into a zigzag supra­molecular chain along [100].

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In the title compound, C15H14N2O2S, the central C2N2OS moiety is planar (r.m.s. deviation of fitted atoms = 0.0336 Å). This is ascribed to the formation of an S(6) loop stabilized by an intra­molecular N—H...O hydrogen bond; additional intramolecular N—H...O and C—H...S contacts are also noted. The dihedral angles between the central unit and the phenyl and benzene rings are 23.79 (7) and 29.52 (5)°, respectively. The thione S and ketone O atoms are mutually anti, as are the N—H H atoms; the O atoms lie to the same side of the mol­ecule. Centrosymmetric eight-membered {...HNC=S}2 synthons feature in the crystal packing. The resulting inversion dimers stack along the a axis and are connected into a three-dimensional structure by C—H...O and C—H...π inter­actions.

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In the title hemisolvate, C14H11ClN2OS·0.5CH2Cl2, an anti disposition is found for the thione and ketone atoms, as well as the N—H H atoms; the dichloro­methane C atom lies on a twofold axis. The central chromophore (including the two adjacent ipso C atoms) is planar (r.m.s. deviation = 0.021 Å) owing to the presence of an intra­molecular N—H...O hydrogen bond, which closes an S(6) loop. Significant twists are evident in the mol­ecule, the dihedral angles between the central moiety and the phenyl and benzene rings being 29.52 (7) and 40.02 (7)°, respectively. In the crystal, eight-membered {...HNC= S}2 synthons with twofold symmetry form via N—H...S hydrogen bonds. The dimers are connected into a supra­molecular chain along [111] by C—H...O inter­actions. The chains stack along the c axis, forming columns which define channels in which the occluded dichloro­methane mol­ecules reside.
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