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The title compounds, both C(13)H(11)NO(3), exist as the keto-amine tautomers, and the formal hydroxyl H atoms, which display strong intramolecular hydrogen bonds, are located on the N atoms. This is a verification of the preference for the keto-amine tautomeric form in the solid state. The 2-hydroxy isomer has two independent molecules, with the molecules linked by intramolecular N-H.O and O-H.O and intermolecular O-H.O hydrogen bonds into three-dimensional networks.

The title compound, C13H11NO3, adopts the keto–amine tautomeric form, with the H atom located on N rather than on O. This H atom is involved in a strong intra­molecular hydrogen bond. There are two independent molecules in the asymmetric unit. The mol­ecules are linked by intra­molecular N—H·O and O—H·O and inter­molecular O—H·O hydrogen bonds into a three‐dimensional network.

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Key indicatorsSingle-crystal X-ray study T = 293 K Mean (C-C) = 0.006 Å R factor = 0.035 wR factor = 0.069 Data-to-parameter ratio = 14.0For details of how these key indicators were automatically derived from the article, see

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Key indicators: single-crystal X-ray study; T = 293 K; mean (C-C) = 0.004 Å; R factor = 0.043; wR factor = 0.112; data-to-parameter ratio = 16.3.In the title compound, C 13 H 18 ClNO 4 , the molecules are linked only by weak van der Waals interactions. The boat form of the six-membered ring is almost symmetric with respect to the epoxy bridge. The three five-membered rings adopt envelope conformations. Related literatureFor related literature, see: Brickwood et al. (1999); Christoffers & Baro (2005); Cremer & Pople (1975); Koşar et al. (2007); Prajapati et al. (1993).Experimental Crystal data C 13 H 18 ClNO 4 M r = 287.73 Monoclinic, P2 1 =c a = 18.7133 (15) Å b = 8.3800 (8) Å c = 9.2123 (7) Å = 90.134 (7) V = 1444.6 (2) Å 3 Z = 4 Mo K radiation = 0.27 mm À1 T = 293 (2) K 0.50 Â 0.32 Â 0.03 mm Data collection Stoe IPDSII diffractometer Absorption correction: integration (X-RED; Stoe & Cie, 2002) T min = 0.911, T max = 0.992 11238 measured reflections 3390 independent reflections 1847 reflections with I > 2(I) R int = 0.045 Refinement R[F 2 > 2(F 2 )] = 0.043 wR(F 2 ) = 0.112 S = 0.88 3390 reflections 208 parametersH atoms treated by a mixture of independent and constrained refinement Á max = 0.16 e Å À3 Á min = À0.17 e Å À3

In this work, the structure of (E)-2-{[2- (hydroxymethyl) phenylimino]methyl}-5-methoxyphenol was characterized by X-ray single crystal diffraction technique, infrared spectroscopy, and quantum chemical computational methods as both experimental and theoretically. The compound crystallizes in the triclinic space group P1 with a ¼ 9.4601 (5) Å , b ¼ 11.7273 (7) Å , c ¼ 12.4400 (8) Å , a ¼ 88.179 (5) , b ¼ 71.442 (4) , c ¼ 84.977 (5) , and Z ¼ 4. X-Ray study shows that both enol-imine and keto-amine tautomeric forms coexist in the asymmetric unit as two independent molecules. The molecular geometry was also optimized at the B3LYP/6-311G(d,p) level by using density functional theory started from the crystallographically achieved parameters of molecule. From the optimized geometry of the molecule, molecular electrostatic potential was evaluated, frontier molecular orbitals and natural bond orbital analysis were performed, and vibrational frequencies were computed theoretically. The polarizable continuum model calculations starting from the optimized geometry were also carried out in both gaseous and solution phase to investigate the energetic behavior and dipole moment of the title compound with the same level of theory. Results and Discussion MOLECULAR GEOMETRYAn ORTEP-3 plot with the atom-numbering scheme of the title compound is shown in Figure 3 FIGURE 1. Enol-imine (a), keto-amine (b), and zwitterionic (c) forms of o-hydroxy Schiff bases.FIGURE 2.