N′-(3-Fluorobenzylidene)-4-hydroxy-3-methoxybenzohydrazide methanol monosolvate

In the title compound, C15H13FN2O3·CH3OH, the dihedral angle between the benzene rings of the benzohydrazone molecule is 5.3 (3)°. The C atom of the methoxy group is almost coplanar with its attached ring [deviation = 0.017 (2) Å]. The r.m.s. deviation of the 21 non-H atoms of the hydrazone molecule is 0.106 Å. In the crystal, the components are linked by Om—H⋯Oh, Nh—H⋯Om and Oh—H⋯Oh (m = methanol and h = hydrazone) hydrogen bonds, forming (001) layers.


Qian-Shou Zong Comment
In this paper, the title new benzohydrazide compound, (I), which crystallised as a methanol solvate, is reported.
The dihedral angle between the benzene rings C1-C6 and C9-C14 of the benzohydrazone molecule is 5.3 (3)°. The bond lengths in the benzohydrazone molecule are comparable to those in similar benzohydrazone compounds (Horkaew et al., 2012;Fun et al., 2011;Zhang, 2011). In the crystal, the benzohydrazone molecules are linked by methanol molecules through hydrogen bonds (Table 1), to form layers parallel to the ab plane (Fig. 2).

Experimental
3-Fluorobenzaldehyde (0.124 g, 1 mmol) and 4-hydroxy-3-methoxybenzohydrazide (0.182 g, 1 mmol) were mixed in methanol. The mixture was stirred at room temperature for 1 h to give a colorless solution. Colourless blocks were obtained by slow evaporation from the solution in air.

Refinement
H1 was located from an electronic map and restrained with N-H distance of 0.90 (1) Å. All other H atoms were placed at calculated positions and refined using a riding model approximation, with C-H = 0.93 or 0.96 Å, O-H = 0.82 Å, and with U iso (H) = 1.2U eq (C) or 1.5U eq (methyl C and O).

Special details
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.