Vyacheslav S. Grinev, Anna E. Sklyar, Ilya A. Demeshko, Anastasia A. Lobankova, Nikita A. Barabanov, Alevtina Yu. Yegorova
{"title":"4-oxo-4-phenylbutanoic acid 多晶体的晶体结构、堆积特征、分子间氢键的 DFT 评估以及晶格能","authors":"Vyacheslav S. Grinev, Anna E. Sklyar, Ilya A. Demeshko, Anastasia A. Lobankova, Nikita A. Barabanov, Alevtina Yu. Yegorova","doi":"10.1007/s11224-024-02351-z","DOIUrl":null,"url":null,"abstract":"<div><p>Different crystal forms of pharmaceutically important compounds demonstrate non-equivalent physical properties and, thus, bioactivity. Taking into consideration the polymorphism is crucial for many applications due to the prominent variation in properties of solids of the same chemical substance but with different crystal packing. The structure of 4-oxo-4-phenylbutanoic acid, C<sub>10</sub>H<sub>10</sub>O<sub>3</sub>, at 120 K has monoclinic (<i>P</i>2<sub>1</sub><i>/c</i>) symmetry and is a <i>Z</i> = 8, <i>Z</i>′ = 2 polymorph (γ-form). The previously published two polymorphs with CCDC codes VERMAG (α-form) and VERMAG01 (β-form) crystallize with <i>Z</i> = 4, <i>Z</i>′ = 1 in the monoclinic space groups <i>P</i>2<sub>1</sub><i>/c</i> [<i>a</i> = 15.071 (10), <i>b</i> = 5.435 (9), <i>c</i> = 16.058 (10), <i>β</i> = 129.57 (10)°] and <i>P</i>2<sub>1</sub><i>/n</i> [<i>a</i> = 12.728 (6), <i>b</i> = 5.200 (3), <i>c</i> = 14.426 (6), <i>β</i> = 111.33 (3)°], respectively. Reported herein polymorph has a significantly larger cell volume of 1754.51 Å<sup>3</sup> [<i>a</i> = 15.2673 (6), <i>b</i> = 5.2028 (2), <i>c</i> = 22.3063 (8), <i>β</i> = 98.0217 (7)°]. Structurally, the γ-form differs from the two other known (RMSD does not exceed 0.2 Å). Only reported herein polymorph contains weak attractive C7—H7A···O3A close contacts between two neighboring molecules, giving some structural variety of the two crystallographically independent molecules as well as slight non-coplanarity between their phenyl rings. The previously reported polymorphs demonstrate carbonyl groups at position 4 unaffected. All polymorphs contain dimers of molecules bounded by two equivalent intermolecular hydrogen bonds. Investigation of three polymorphs of 4-oxo-4-phenylbutanoic acid highlights the importance of understanding the relationship between various parameters such as packing density, presence of different interactions within the crystal, and energy of the crystal lattice. This is of great importance for the development of new materials with specific physical properties and applications in various fields of science and technology, such as dyes and pigments, high-energy materials, and pharmaceuticals.</p></div>","PeriodicalId":780,"journal":{"name":"Structural Chemistry","volume":"35 6","pages":"2045 - 2053"},"PeriodicalIF":2.1000,"publicationDate":"2024-06-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Crystal structure, packing features, DFT evaluation of intermolecular hydrogen bonds, and crystal lattice energy of a polymorph of 4-oxo-4-phenylbutanoic acid\",\"authors\":\"Vyacheslav S. Grinev, Anna E. Sklyar, Ilya A. Demeshko, Anastasia A. Lobankova, Nikita A. Barabanov, Alevtina Yu. Yegorova\",\"doi\":\"10.1007/s11224-024-02351-z\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Different crystal forms of pharmaceutically important compounds demonstrate non-equivalent physical properties and, thus, bioactivity. Taking into consideration the polymorphism is crucial for many applications due to the prominent variation in properties of solids of the same chemical substance but with different crystal packing. The structure of 4-oxo-4-phenylbutanoic acid, C<sub>10</sub>H<sub>10</sub>O<sub>3</sub>, at 120 K has monoclinic (<i>P</i>2<sub>1</sub><i>/c</i>) symmetry and is a <i>Z</i> = 8, <i>Z</i>′ = 2 polymorph (γ-form). The previously published two polymorphs with CCDC codes VERMAG (α-form) and VERMAG01 (β-form) crystallize with <i>Z</i> = 4, <i>Z</i>′ = 1 in the monoclinic space groups <i>P</i>2<sub>1</sub><i>/c</i> [<i>a</i> = 15.071 (10), <i>b</i> = 5.435 (9), <i>c</i> = 16.058 (10), <i>β</i> = 129.57 (10)°] and <i>P</i>2<sub>1</sub><i>/n</i> [<i>a</i> = 12.728 (6), <i>b</i> = 5.200 (3), <i>c</i> = 14.426 (6), <i>β</i> = 111.33 (3)°], respectively. Reported herein polymorph has a significantly larger cell volume of 1754.51 Å<sup>3</sup> [<i>a</i> = 15.2673 (6), <i>b</i> = 5.2028 (2), <i>c</i> = 22.3063 (8), <i>β</i> = 98.0217 (7)°]. Structurally, the γ-form differs from the two other known (RMSD does not exceed 0.2 Å). Only reported herein polymorph contains weak attractive C7—H7A···O3A close contacts between two neighboring molecules, giving some structural variety of the two crystallographically independent molecules as well as slight non-coplanarity between their phenyl rings. The previously reported polymorphs demonstrate carbonyl groups at position 4 unaffected. All polymorphs contain dimers of molecules bounded by two equivalent intermolecular hydrogen bonds. Investigation of three polymorphs of 4-oxo-4-phenylbutanoic acid highlights the importance of understanding the relationship between various parameters such as packing density, presence of different interactions within the crystal, and energy of the crystal lattice. This is of great importance for the development of new materials with specific physical properties and applications in various fields of science and technology, such as dyes and pigments, high-energy materials, and pharmaceuticals.</p></div>\",\"PeriodicalId\":780,\"journal\":{\"name\":\"Structural Chemistry\",\"volume\":\"35 6\",\"pages\":\"2045 - 2053\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-06-14\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Structural Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s11224-024-02351-z\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Structural Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s11224-024-02351-z","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Crystal structure, packing features, DFT evaluation of intermolecular hydrogen bonds, and crystal lattice energy of a polymorph of 4-oxo-4-phenylbutanoic acid
Different crystal forms of pharmaceutically important compounds demonstrate non-equivalent physical properties and, thus, bioactivity. Taking into consideration the polymorphism is crucial for many applications due to the prominent variation in properties of solids of the same chemical substance but with different crystal packing. The structure of 4-oxo-4-phenylbutanoic acid, C10H10O3, at 120 K has monoclinic (P21/c) symmetry and is a Z = 8, Z′ = 2 polymorph (γ-form). The previously published two polymorphs with CCDC codes VERMAG (α-form) and VERMAG01 (β-form) crystallize with Z = 4, Z′ = 1 in the monoclinic space groups P21/c [a = 15.071 (10), b = 5.435 (9), c = 16.058 (10), β = 129.57 (10)°] and P21/n [a = 12.728 (6), b = 5.200 (3), c = 14.426 (6), β = 111.33 (3)°], respectively. Reported herein polymorph has a significantly larger cell volume of 1754.51 Å3 [a = 15.2673 (6), b = 5.2028 (2), c = 22.3063 (8), β = 98.0217 (7)°]. Structurally, the γ-form differs from the two other known (RMSD does not exceed 0.2 Å). Only reported herein polymorph contains weak attractive C7—H7A···O3A close contacts between two neighboring molecules, giving some structural variety of the two crystallographically independent molecules as well as slight non-coplanarity between their phenyl rings. The previously reported polymorphs demonstrate carbonyl groups at position 4 unaffected. All polymorphs contain dimers of molecules bounded by two equivalent intermolecular hydrogen bonds. Investigation of three polymorphs of 4-oxo-4-phenylbutanoic acid highlights the importance of understanding the relationship between various parameters such as packing density, presence of different interactions within the crystal, and energy of the crystal lattice. This is of great importance for the development of new materials with specific physical properties and applications in various fields of science and technology, such as dyes and pigments, high-energy materials, and pharmaceuticals.
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Structural Chemistry is an international forum for the publication of peer-reviewed original research papers that cover the condensed and gaseous states of matter and involve numerous techniques for the determination of structure and energetics, their results, and the conclusions derived from these studies. The journal overcomes the unnatural separation in the current literature among the areas of structure determination, energetics, and applications, as well as builds a bridge to other chemical disciplines. Ist comprehensive coverage encompasses broad discussion of results, observation of relationships among various properties, and the description and application of structure and energy information in all domains of chemistry.
We welcome the broadest range of accounts of research in structural chemistry involving the discussion of methodologies and structures,experimental, theoretical, and computational, and their combinations. We encourage discussions of structural information collected for their chemicaland biological significance.
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