Two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine
Two monoclinic (P21/c; Z′ = 1) polymorphs, α (from methanol) and β (from ethanol, n-propanol and iso-propanol), of a bioactive pyrazolo[3,4-d]pyrimidine derivative have been isolated and characterised by X-ray crystallography as well as by a range of computational chemistry techniques. The different...
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MDPI
2023
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| Online Access: | http://eprints.sunway.edu.my/2289/ http://eprints.sunway.edu.my/2289/1/crystals%202023%2013%20974.pdf |
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| author | Tan, Sang Loon * Tan, Yee Seng * Ng, Jia Hui Dolzhenko, Anton V Tiekink, Edward R. T. * |
| author_facet | Tan, Sang Loon * Tan, Yee Seng * Ng, Jia Hui Dolzhenko, Anton V Tiekink, Edward R. T. * |
| author_sort | Tan, Sang Loon * |
| building | SU Institutional Repository |
| collection | Online Access |
| description | Two monoclinic (P21/c; Z′ = 1) polymorphs, α (from methanol) and β (from ethanol, n-propanol and iso-propanol), of a bioactive pyrazolo[3,4-d]pyrimidine derivative have been isolated and characterised by X-ray crystallography as well as by a range of computational chemistry techniques. The different conformations observed for the molecules in the crystals are due to the dictates of molecular packing as revealed by geometry-optimisation calculations. The crucial difference in the molecular packing pertains to the formation of phenylamino-N–H···N(pyrazolyl) hydrogen bonding within supramolecular chains with either helical (α-form; 21-screw symmetry) or zigzag (β-form; glide symmetry). As a consequence, the molecular packing is quite distinct in the polymorphs. Lattice energy calculations indicate the β-form is more stable by 11 kJ/mol than the α-form. |
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| format | Article |
| id | sunway-2289 |
| institution | Sunway University |
| institution_category | Local University |
| language | English |
| last_indexed | 2025-11-14T21:20:20Z |
| publishDate | 2023 |
| publisher | MDPI |
| recordtype | eprints |
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| spelling | sunway-22892023-06-20T00:13:01Z http://eprints.sunway.edu.my/2289/ Two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine Tan, Sang Loon * Tan, Yee Seng * Ng, Jia Hui Dolzhenko, Anton V Tiekink, Edward R. T. * QD Chemistry Two monoclinic (P21/c; Z′ = 1) polymorphs, α (from methanol) and β (from ethanol, n-propanol and iso-propanol), of a bioactive pyrazolo[3,4-d]pyrimidine derivative have been isolated and characterised by X-ray crystallography as well as by a range of computational chemistry techniques. The different conformations observed for the molecules in the crystals are due to the dictates of molecular packing as revealed by geometry-optimisation calculations. The crucial difference in the molecular packing pertains to the formation of phenylamino-N–H···N(pyrazolyl) hydrogen bonding within supramolecular chains with either helical (α-form; 21-screw symmetry) or zigzag (β-form; glide symmetry). As a consequence, the molecular packing is quite distinct in the polymorphs. Lattice energy calculations indicate the β-form is more stable by 11 kJ/mol than the α-form. MDPI 2023-06-19 Article PeerReviewed text en cc_by_4 http://eprints.sunway.edu.my/2289/1/crystals%202023%2013%20974.pdf Tan, Sang Loon * and Tan, Yee Seng * and Ng, Jia Hui and Dolzhenko, Anton V and Tiekink, Edward R. T. * (2023) Two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine. Crystals, 13 (6). p. 974. ISSN 2073-4352 https://www.mdpi.com/2073-4352/13/6/974 10.3390/cryst13060974 |
| spellingShingle | QD Chemistry Tan, Sang Loon * Tan, Yee Seng * Ng, Jia Hui Dolzhenko, Anton V Tiekink, Edward R. T. * Two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine |
| title | Two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine |
| title_full | Two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine |
| title_fullStr | Two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine |
| title_full_unstemmed | Two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine |
| title_short | Two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine |
| title_sort | two conformational polymorphs of a bioactive pyrazolo[3,4-d]pyrimidine |
| topic | QD Chemistry |
| url | http://eprints.sunway.edu.my/2289/ http://eprints.sunway.edu.my/2289/ http://eprints.sunway.edu.my/2289/ http://eprints.sunway.edu.my/2289/1/crystals%202023%2013%20974.pdf |