Polymorphism in <i>N</i>-(3-Hydroxyphenyl)-3-methoxybenzamide
<i>N</i>-(3-hydroxyphenyl)-3-methoxybenzamide was synthesised by amide coupling. After crystallisation, single-crystal X-ray diffraction revealed two distinct polymorphs of the compound: one in the orthorhombic space group <i>Pna</i>2<sub>1</sub> with one molecule...
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| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-12-01
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| Series: | Crystals |
| Subjects: | |
| Online Access: | https://www.mdpi.com/2073-4352/14/12/1070 |
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| Summary: | <i>N</i>-(3-hydroxyphenyl)-3-methoxybenzamide was synthesised by amide coupling. After crystallisation, single-crystal X-ray diffraction revealed two distinct polymorphs of the compound: one in the orthorhombic space group <i>Pna</i>2<sub>1</sub> with one molecule in the asymmetric unit (<i>Z</i>′ = 1) and a second in the triclinic space group <i>P</i>-1 with two molecules in the asymmetric unit (<i>Z</i>′ = 2). A comparison of the structures reveals that the differences between the two can be attributed to conformational variations, disorder, and the dimensionality of the hydrogen bonding networks, with one forming a three-dimensional net and the other forming layers that exhibit approximate <i>p</i>2<sub>1</sub>/<i>b</i>11 layer group symmetry. Molecular dynamics simulations and well-tempered metadynamics-enhanced sampling calculations provide insight into the transition of one polymorph into the other at room temperature. The efficiency of the crystal packing is assessed by a comparison of the densities and melting points of the two structures. |
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| ISSN: | 2073-4352 |