Synthesis and crystal structure of 2-(2-hydroxyphenyl)-1,3-bis(4-methoxybenzyl)-1,3-diazinan-5-ol

  • The redetermined structure of 2-(2-hy­droxy­phen­yl)-1,3-bis­(4-meth­oxy­benz­yl)-1,3-diazinan-5-ol, C26H30N2O4, at 173 K has ortho­rhom­bic (Pbca) symmetry. It was previously described by Bolte et al. [ Private Communication (refcode EWICEV). CCDC, Cambridge, England]. The title compound resulted from the condensation reaction between 1,3-bis­{[(4-meth­oxy­phen­yl)meth­yl]amino}­propan-2-ol and 2-hy­droxy­benzaldehyde in CH3OH. The structure exhibits disorder. One of the 4-meth­oxy­benzyl groups, the hy­droxy group bonded to the 1,3-diazinan ring, and the methyl group of the meth­oxy residue are disordered over two orientations, with occupancies of 0.807 (3)/0.193 (3), 0.642 (5)/0.358 (5), and 0.82 (4)/0.18 (4), respectively. The dihedral angles between the mean planes of the central 1,3-diazinan-5-ol and the 4-meth­oxy­phenyl rings (both occupancy components of the disordered ring) are 88.65 (13), 85.79 (14) and 83.4 (7)°. The crystal packing is sustained by C—H...O and O—H...π inter­actions, giving rise to infinite chains running along the b-axis direction.

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Author:Augusto RiveraORCiD, Jaime Ríos-MottaORCiD, Michael BolteORCiD
Parent Title (English):Acta Crystallographica. Section E, Crystallographic communications
Publisher:International Union of Crystallography
Place of publication:Chester
Document Type:Article
Year of Completion:2022
Year of first Publication:2022
Publishing Institution:Universitätsbibliothek Johann Christian Senckenberg
Release Date:2023/09/20
Tag:C-H...O interactions; Mannich-type bases; O-H...[pi] interactions; crystal structure; hexahydropyrimidine; intramolecular hydrogen bond
Page Number:12
First Page:742
Last Page:745
Institutes:Biochemie, Chemie und Pharmazie / Biochemie und Chemie
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 540 Chemie und zugeordnete Wissenschaften
Licence (German):License LogoCreative Commons - CC BY - Namensnennung 4.0 International