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Synthesis and crystal structure of 1,3-bis(4-hydroxyphenyl)- 1H-imidazol-3-ium chloride.
- Source :
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Acta Crystallographica Section E: Crystallographic Communications . Sep2019, Vol. 75 Issue 9, Following p1311-1315. 10p. - Publication Year :
- 2019
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Abstract
- Imidazolium salts are common building blocks for functional materials and in the synthesis of N-heterocyclic carbene (NHC) as σ-donor ligands for stable metal complexes. The title salt, 1,3-bis­(4-hy­droxy­phen­yl)-1H-imidazol-3-ium chloride (IOH·Cl), C15H13N2O2+·Cl−, is a new imidazolium salt with a hy­droxy functionality. The synthesis of IOH·Cl was achieved in high yield via a two-step procedure involving a di­aza­butadiene precursor followed by ring closure using tri­methylchloro­silane and paraformaldehyde. The structure of IOH·Cl consists of a central planar imidazolium ring (r.m.s. deviation = 0.0015 Å), with out-of-plane phenolic side arms. The dihedral angles between the 4-hy­droxy­phenyl substituents and the imidazole ring are 55.27 (7) and 48.85 (11)°. In the crystal, O—H···Cl hydrogen bonds connect the distal hy­droxy groups and Cl− anions in adjacent asymmetric units, one related by inversion (−x + 1, −y + 1, −z + 1) and one by the n-glide (x − ½, −y + ½, z − ½), with donor–acceptor distances of 2.977 (2) and 3.0130 (18) Å, respectively. The phenolic rings are each π–π stacked with their respective inversion-related [(−x + 1, −y + 1, −z + 1) and (−x, −y + 1, −z + 1)] counterparts, with inter­planar distances of 3.560 (3) and 3.778 (3) Å. The only other noteworthy inter­molecular inter­action is an O...O (not hydrogen bonded) close contact of 2.999 (3) Å between crystallographically different hy­droxy O atoms on translationally adjacent mol­ecules (x + 1, y, x + 1). [ABSTRACT FROM AUTHOR]
- Subjects :
- *CRYSTAL structure
*DIHEDRAL angles
*CHLORIDES
*HYDROGEN bonding
*SALT
Subjects
Details
- Language :
- English
- ISSN :
- 20569890
- Volume :
- 75
- Issue :
- 9
- Database :
- Academic Search Index
- Journal :
- Acta Crystallographica Section E: Crystallographic Communications
- Publication Type :
- Academic Journal
- Accession number :
- 138445909
- Full Text :
- https://doi.org/10.1107/S2056989019011058