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. 2019 Mar 26;75(Pt 4):470-474.
doi: 10.1107/S2056989019003220. eCollection 2019 Apr 1.

(Z)-3-({[3-Meth-oxy-5-(tri-fluoro-meth-yl)phen-yl]imino}meth-yl)benzene-1,2-diol

Sibel Demir Kanmazalp  1 , Onur Erman Doĝan  2 , Necmi Dege  3 , Erbil Aĝar  2 , Hakan Bulbul  3 , Irina A Golenya  4
Affiliations

(Z)-3-({[3-Meth-oxy-5-(tri-fluoro-meth-yl)phen-yl]imino}meth-yl)benzene-1,2-diol

Sibel Demir Kanmazalp et al. Acta Crystallogr E Crystallogr Commun. .

Abstract

The title compound, C15H12F3NO3, crystallizes with one mol-ecule in the asymmetric unit. The mean planes of the two phenyl rings of the Schiff base moiety, bearing the OH groups and the imine group, respectively, are inclined to each other by 4.91 (1)°. In the crystal, mol-ecules are linked via pairs of bifurcated O-H⋯O hydrogen bonds between the phenol OH groups, forming inversion dimers with an R 1 2(5) ring motif. The structure exhibits also intra-molecular O-H⋯N and C-H⋯F hydrogen-bonding inter-actions. Hirshfeld surfaces analysis and two-dimensional fingerprint plots were applied to qu-antify the inter-molecular inter-actions. The three F atoms of the tri-fluoro-methyl group are disordered over two sets of sites, with occupancy factors of 0.578 (8) and 0.422 (8). The crystal studied was refined as an inversion twin.

Keywords: Hirshfeld surface analysis; O⋯O inter­action; Schiff base; crystal structure.

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Figures

Figure 1
Figure 1
The mol­ecular structure of the title compound with the atomic numbering scheme. The dashed line shows the intra­molecular O—H⋯N hydrogen bond. Displacement ellipsoids are drawn at the 50% probability level.
Figure 2
Figure 2
Unit-cell packing diagram for the title compound. Intra- and inter­molecular hydrogen bonds are shown as dashed lines. [Symmetry code: (i) −x − 1, −y, z − formula image.]
Figure 3
Figure 3
View of the three-dimensional Hirshfeld surface of the title compound plotted over d norm (in the range −0.211 to 1.077 a.u.), d e and d i.
Figure 4
Figure 4
Two-dimensional fingerprint plots of the crystal with the relative contributions of the atom pairs to the Hirshfeld surface.
Figure 5
Figure 5
Hirshfeld surface mapped over d norm to visualize the inter­molecular inter­actions.
See this image and copyright information in PMC

References

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