(E)-4-[(4-Fluorobenzylidene)amino]-3-[1-(4-isobutylphenyl)ethyl]-1-(morpholinomethyl)-1H-1,2,4-triazole-5(4H)-thione methanol hemisolvate

In the title compound, C26H32FN5OS·0.5CH4O, the methyl group of the methanol solvent molecule is disordered over two sites with equal occupancies and the solvent is further disordered about a crystallographic twofold rotation axis. The organic molecule exists in a trans configuration with respect to the acyclic C=N bond. An intramolecular C—H⋯S hydrogen bond generates an S(6) ring motif. The morpholine ring adopts a chair conformation. The essentially planar 1,2,4-triazole ring [maximum deviation = 0.013 (2) Å] forms dihedral angles of 11.21 (10) and 67.53 (11)°, respectively, with the fluorophenyl unit and the isobutyl-substituted benzene ring. The crystal structure is stabilized by a weak intermolecular C—H⋯π interaction.

In the title compound, C 26 H 32 FN 5 OSÁ0.5CH 4 O, the methyl group of the methanol solvent molecule is disordered over two sites with equal occupancies and the solvent is further disordered about a crystallographic twofold rotation axis. The organic molecule exists in a trans configuration with respect to the acyclic C N bond. An intramolecular C-HÁ Á ÁS hydrogen bond generates an S(6) ring motif. The morpholine ring adopts a chair conformation. The essentially planar 1,2,4-triazole ring [maximum deviation = 0.013 (2) Å ] forms dihedral angles of 11.21 (10) and 67.53 (11) , respectively, with the fluorophenyl unit and the isobutyl-substituted benzene ring. The crystal structure is stabilized by a weak intermolecular C-HÁ Á Á interaction.
The bond lengths and angles are consistent to those observed in closely related structures (Goh et al., 2010a,b).
In the crystal structure, no significant intermolecular hydrogen bonds are observed. The crystal structure is stabilized by a weak intermolecular C22-H22A···Cg1 interactions (Table 1) involving the 1,2,4-triazole ring.

Experimental
A mixture of Schiff base (0.01 mol) and formaldehyde (40 %, 2 ml) in ethanol (15 ml) was taken to this solution morpholine (0.01 mol) was added. The reaction mixture was stirred at room temperature for two days. The solid product obtained was collected by filtration, washed with ethanol and dried. Colourless single crystals suitable for X-ray analysis were obtained from a 1:2 mixture of N,N-dimethylformamide and methanol by slow evaporation.

Refinement
All hydrogen atoms were placed in their calculated positions, with C-H = 0.93 -0.98 Å, and refined using a riding model with U iso = 1.2 or 1.5 U eq (C). A rotating group model was used for the C19, C20 and C21 methyl groups. The methanol solvent molecule is refined with a fixed occupancy of 0.5. The atom C27 of methanol solvent molecule is disordered over two positions with an equal occupancy of 0.25. Both the disordered components are further disordered over a crystallography two-fold rotation. A short intermolecular H15A···H27E interactions [2.04 Å] is also observed. Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme. An intramolecular hydrogen bond is shown as dashed line. The open bond in the solvent molecule indicates a disordered component.

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.