[3-({(E)-2-[(4-Fluorophenyl)carbamo-thioyl]hydrazinylidene}methyl)-4-hy-droxy-benzyl]methyl-triphenyl-phos-phonium chloride

Abstract

The cation in the title salt, C(33)H(28)FN(3)OPS(+)·Cl(-), is highly twisted with the phospho-nium group occupying a position almost normal to the central hydroxyl-benzene ring [P-C-C-C tosrsion angle = -100.9 (3)°], and with the hydrazone substituent twisted out of the plane [C-C-C-N torsion angle = 13.1 (4)°]. The fluoro-benzene ring is twisted out of the plane of the adjacent thio-urea residue, forming a dihedral angle of 51.69 (10)°. The configuration about the C=N bond [1.281 (4) Å] is E, the O-H and N-H hydrogen atoms are syn, and in the thio-urea residue, the N-H hydrogen atoms are anti, allowing for the formation of an intra-molecular N-H⋯N hydrogen bond. In the crystal, dimeric aggregates mediated by N-H⋯S bonds are formed, which are linked to the Cl(-) anions by O-H⋯Cl hydrogen bonds. The four-component aggregates are linked into a three-dimensional structure by C-H⋯Cl inter-actions.

Fig. 1.

The molecular structures of the ions comprising the asymmetric unit of (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level.

Fig. 2.

A view in projection down the b axis of the crystal packing in (I) highlighting the mode of association between the constituent ions. The N—H···S, O—H···Cl and C—H···Cl interactions are shown as orange, blue and brown dashed lines, respectively.

Fig. 3.

A view in projection down the c axis of the crystal packing in (I) highlighting the stacking of layers along the a-direction. The N—H···S, O—H···Cl and C—H···Cl interactions are shown as orange, blue and brown dashed lines, respectively.