Two Conformational Polymorphs of a Bioactive Pyrazolo[3,4-<i>d</i>]pyrimidine
Two monoclinic (<i>P</i>2<sub>1</sub>/<i>c</i>; <i>Z</i>′ = 1) polymorphs, <b>α</b> (from methanol) and <b>β</b> (from ethanol, n-propanol and iso-propanol), of a bioactive pyrazolo[3,4-<i>d</i>]pyrimidine derivative...
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| Format: | Article |
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MDPI AG
2023-06-01
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| Series: | Crystals |
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| Online Access: | https://www.mdpi.com/2073-4352/13/6/974 |
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| author | Sang Loon Tan Yee Seng Tan Jia Hui Ng Anton V. Dolzhenko Edward R. T. Tiekink |
| author_facet | Sang Loon Tan Yee Seng Tan Jia Hui Ng Anton V. Dolzhenko Edward R. T. Tiekink |
| author_sort | Sang Loon Tan |
| collection | DOAJ |
| description | Two monoclinic (<i>P</i>2<sub>1</sub>/<i>c</i>; <i>Z</i>′ = 1) polymorphs, <b>α</b> (from methanol) and <b>β</b> (from ethanol, n-propanol and iso-propanol), of a bioactive pyrazolo[3,4-<i>d</i>]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 (<b>α</b>-form; 2<sub>1</sub>-screw symmetry) or zigzag (<b>β</b>-form; glide symmetry). As a consequence, the molecular packing is quite distinct in the polymorphs. Lattice energy calculations indicate the <b>β</b>-form is more stable by 11 kJ/mol than the <b>α</b>-form. |
| first_indexed | 2024-03-11T02:35:49Z |
| format | Article |
| id | doaj.art-6bf93431df4f48e488007425136fdc94 |
| institution | Directory Open Access Journal |
| issn | 2073-4352 |
| language | English |
| last_indexed | 2024-03-11T02:35:49Z |
| publishDate | 2023-06-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Crystals |
| spelling | doaj.art-6bf93431df4f48e488007425136fdc942023-11-18T09:57:21ZengMDPI AGCrystals2073-43522023-06-0113697410.3390/cryst13060974Two Conformational Polymorphs of a Bioactive Pyrazolo[3,4-<i>d</i>]pyrimidineSang Loon Tan0Yee Seng Tan1Jia Hui Ng2Anton V. Dolzhenko3Edward R. T. Tiekink4Research Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, Bandar Sunway 47500, Selangor Darul Ehsan, MalaysiaResearch Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, Bandar Sunway 47500, Selangor Darul Ehsan, MalaysiaSchool of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway 47500, Selangor Darul Ehsan, MalaysiaSchool of Pharmacy, Monash University Malaysia, Jalan Lagoon Selatan, Bandar Sunway 47500, Selangor Darul Ehsan, MalaysiaResearch Centre for Crystalline Materials, School of Medical and Life Sciences, Sunway University, Bandar Sunway 47500, Selangor Darul Ehsan, MalaysiaTwo monoclinic (<i>P</i>2<sub>1</sub>/<i>c</i>; <i>Z</i>′ = 1) polymorphs, <b>α</b> (from methanol) and <b>β</b> (from ethanol, n-propanol and iso-propanol), of a bioactive pyrazolo[3,4-<i>d</i>]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 (<b>α</b>-form; 2<sub>1</sub>-screw symmetry) or zigzag (<b>β</b>-form; glide symmetry). As a consequence, the molecular packing is quite distinct in the polymorphs. Lattice energy calculations indicate the <b>β</b>-form is more stable by 11 kJ/mol than the <b>α</b>-form.https://www.mdpi.com/2073-4352/13/6/974polymorphismcrystal structurelattice energyHirshfeld surface analysisinteraction energy |
| spellingShingle | Sang Loon Tan Yee Seng Tan Jia Hui Ng Anton V. Dolzhenko Edward R. T. Tiekink Two Conformational Polymorphs of a Bioactive Pyrazolo[3,4-<i>d</i>]pyrimidine Crystals polymorphism crystal structure lattice energy Hirshfeld surface analysis interaction energy |
| title | Two Conformational Polymorphs of a Bioactive Pyrazolo[3,4-<i>d</i>]pyrimidine |
| title_full | Two Conformational Polymorphs of a Bioactive Pyrazolo[3,4-<i>d</i>]pyrimidine |
| title_fullStr | Two Conformational Polymorphs of a Bioactive Pyrazolo[3,4-<i>d</i>]pyrimidine |
| title_full_unstemmed | Two Conformational Polymorphs of a Bioactive Pyrazolo[3,4-<i>d</i>]pyrimidine |
| title_short | Two Conformational Polymorphs of a Bioactive Pyrazolo[3,4-<i>d</i>]pyrimidine |
| title_sort | two conformational polymorphs of a bioactive pyrazolo 3 4 i d i pyrimidine |
| topic | polymorphism crystal structure lattice energy Hirshfeld surface analysis interaction energy |
| url | https://www.mdpi.com/2073-4352/13/6/974 |
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