Marimuthu Sangavi, Narayanasamy Kumaraguru, Ray J Butcher, Colin D McMillen
{"title":"5-氟胞嘧啶脲（2/1）、5-氟胞嘧啶-5-氟胞嘧啶鎓-3,5-二硝基水杨酸盐（2/1/1）和 2-氨基-4-氯-6-甲基嘧啶-6-氯烟酸（1/1）中的氢键相互作用。","authors":"Marimuthu Sangavi, Narayanasamy Kumaraguru, Ray J Butcher, Colin D McMillen","doi":"10.1107/S2053229624000615","DOIUrl":null,"url":null,"abstract":"<p><p>Three new compounds, namely, 5-fluorocytosine-urea (2/1), 2C<sub>4</sub>H<sub>4</sub>FN<sub>3</sub>O·CH<sub>4</sub>N<sub>2</sub>O, (I), 5-fluorocytosine-5-fluorocytosinium 3,5-dinitrosalicylate-water (2/1/1), 2C<sub>4</sub>H<sub>4</sub>FN<sub>3</sub>O·C<sub>4</sub>H<sub>5</sub>FN<sub>3</sub>O<sup>+</sup>·C<sub>7</sub>H<sub>2</sub>N<sub>2</sub>O<sub>7</sub><sup>-</sup>·H<sub>2</sub>O, (II), and 2-amino-4-chloro-6-methylpyrimidine-6-chloronicotinic acid (1/1), C<sub>6</sub>H<sub>4</sub>ClNO<sub>2</sub>·C<sub>5</sub>H<sub>6</sub>ClN<sub>3</sub>, (III), have been synthesized and characterized by single-crystal X-ray diffraction. In compound (I), 5-fluorocytosine (5FC) molecules A and B form two different homosynthons [R<sub>2</sub><sup>2</sup>(8) ring motif], one formed via N-H...O hydrogen bonds and the second via N-H...N hydrogen bonds. In addition to this interaction, a sequence of fused-ring motifs [R<sub>2</sub><sup>1</sup>(6), R<sub>3</sub><sup>3</sup>(8), R<sub>2</sub><sup>2</sup>(8), R<sub>4</sub><sup>3</sup>(10) and R<sub>2</sub><sup>2</sup>(8)] are formed, generating a supramolecular ladder-like hydrogen-bonded pattern. In compound (II), 5FC and 5-fluorocytosinium are linked by triple hydrogen bonds, generating two fused-ring motifs [R<sub>2</sub><sup>2</sup>(8)]. The neutral 5FC and protonated 5-fluorocytosinum cation form a dimeric synthon [R<sub>2</sub><sup>2</sup>(8) ring motif] via N-H...O and N-H...N hydrogen bonds. On either side of the dimeric synthon, the neutral 5FC, 5-fluorocytosinium cation, 3,5-dinitrosalicylate anion and water molecule are hydrogen bonded through N-H...O, N-H...N, N-H...OW and OW-HW...O hydrogen bonds, forming a large ring motif [R<sub>10</sub><sup>10</sup>(56)], leading to a three-dimensional supramolecular network. In compound (III), 2-amino-4-chloro-6-methylpyrimidine (ACP) interacts with the carboxylic acid group of 6-chloronicotinic acid via N-H...O and O-H...O hydrogen bonds, generating an R<sub>2</sub><sup>2</sup>(8) primary ring motif. Furthermore, the ACP molecules form a base pair via N-H...N hydrogen bonds. The primary motif and base pair combine to form tetrameric units, which are further connected by Cl...Cl interactions. In addition to this hydrogen-bonding interaction, compounds (I) and (III) are further enriched by π-π stacking interactions.</p>","PeriodicalId":7115,"journal":{"name":"Acta Crystallographica Section C Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":0.7000,"publicationDate":"2024-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Hydrogen-bonding interactions in 5-fluorocytosine-urea (2/1), 5-fluorocytosine-5-fluorocytosinium 3,5-dinitrosalicylate-water (2/1/1) and 2-amino-4-chloro-6-methylpyrimidine-6-chloronicotinic acid (1/1).\",\"authors\":\"Marimuthu Sangavi, Narayanasamy Kumaraguru, Ray J Butcher, Colin D McMillen\",\"doi\":\"10.1107/S2053229624000615\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Three new compounds, namely, 5-fluorocytosine-urea (2/1), 2C<sub>4</sub>H<sub>4</sub>FN<sub>3</sub>O·CH<sub>4</sub>N<sub>2</sub>O, (I), 5-fluorocytosine-5-fluorocytosinium 3,5-dinitrosalicylate-water (2/1/1), 2C<sub>4</sub>H<sub>4</sub>FN<sub>3</sub>O·C<sub>4</sub>H<sub>5</sub>FN<sub>3</sub>O<sup>+</sup>·C<sub>7</sub>H<sub>2</sub>N<sub>2</sub>O<sub>7</sub><sup>-</sup>·H<sub>2</sub>O, (II), and 2-amino-4-chloro-6-methylpyrimidine-6-chloronicotinic acid (1/1), C<sub>6</sub>H<sub>4</sub>ClNO<sub>2</sub>·C<sub>5</sub>H<sub>6</sub>ClN<sub>3</sub>, (III), have been synthesized and characterized by single-crystal X-ray diffraction. In compound (I), 5-fluorocytosine (5FC) molecules A and B form two different homosynthons [R<sub>2</sub><sup>2</sup>(8) ring motif], one formed via N-H...O hydrogen bonds and the second via N-H...N hydrogen bonds. In addition to this interaction, a sequence of fused-ring motifs [R<sub>2</sub><sup>1</sup>(6), R<sub>3</sub><sup>3</sup>(8), R<sub>2</sub><sup>2</sup>(8), R<sub>4</sub><sup>3</sup>(10) and R<sub>2</sub><sup>2</sup>(8)] are formed, generating a supramolecular ladder-like hydrogen-bonded pattern. In compound (II), 5FC and 5-fluorocytosinium are linked by triple hydrogen bonds, generating two fused-ring motifs [R<sub>2</sub><sup>2</sup>(8)]. The neutral 5FC and protonated 5-fluorocytosinum cation form a dimeric synthon [R<sub>2</sub><sup>2</sup>(8) ring motif] via N-H...O and N-H...N hydrogen bonds. On either side of the dimeric synthon, the neutral 5FC, 5-fluorocytosinium cation, 3,5-dinitrosalicylate anion and water molecule are hydrogen bonded through N-H...O, N-H...N, N-H...OW and OW-HW...O hydrogen bonds, forming a large ring motif [R<sub>10</sub><sup>10</sup>(56)], leading to a three-dimensional supramolecular network. In compound (III), 2-amino-4-chloro-6-methylpyrimidine (ACP) interacts with the carboxylic acid group of 6-chloronicotinic acid via N-H...O and O-H...O hydrogen bonds, generating an R<sub>2</sub><sup>2</sup>(8) primary ring motif. Furthermore, the ACP molecules form a base pair via N-H...N hydrogen bonds. The primary motif and base pair combine to form tetrameric units, which are further connected by Cl...Cl interactions. In addition to this hydrogen-bonding interaction, compounds (I) and (III) are further enriched by π-π stacking interactions.</p>\",\"PeriodicalId\":7115,\"journal\":{\"name\":\"Acta Crystallographica Section C Structural Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":0.7000,\"publicationDate\":\"2024-02-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Acta Crystallographica Section C Structural Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1107/S2053229624000615\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2024/1/23 0:00:00\",\"PubModel\":\"Epub\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Acta Crystallographica Section C Structural Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1107/S2053229624000615","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/1/23 0:00:00","PubModel":"Epub","JCR":"Q4","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Hydrogen-bonding interactions in 5-fluorocytosine-urea (2/1), 5-fluorocytosine-5-fluorocytosinium 3,5-dinitrosalicylate-water (2/1/1) and 2-amino-4-chloro-6-methylpyrimidine-6-chloronicotinic acid (1/1).
Three new compounds, namely, 5-fluorocytosine-urea (2/1), 2C4H4FN3O·CH4N2O, (I), 5-fluorocytosine-5-fluorocytosinium 3,5-dinitrosalicylate-water (2/1/1), 2C4H4FN3O·C4H5FN3O+·C7H2N2O7-·H2O, (II), and 2-amino-4-chloro-6-methylpyrimidine-6-chloronicotinic acid (1/1), C6H4ClNO2·C5H6ClN3, (III), have been synthesized and characterized by single-crystal X-ray diffraction. In compound (I), 5-fluorocytosine (5FC) molecules A and B form two different homosynthons [R22(8) ring motif], one formed via N-H...O hydrogen bonds and the second via N-H...N hydrogen bonds. In addition to this interaction, a sequence of fused-ring motifs [R21(6), R33(8), R22(8), R43(10) and R22(8)] are formed, generating a supramolecular ladder-like hydrogen-bonded pattern. In compound (II), 5FC and 5-fluorocytosinium are linked by triple hydrogen bonds, generating two fused-ring motifs [R22(8)]. The neutral 5FC and protonated 5-fluorocytosinum cation form a dimeric synthon [R22(8) ring motif] via N-H...O and N-H...N hydrogen bonds. On either side of the dimeric synthon, the neutral 5FC, 5-fluorocytosinium cation, 3,5-dinitrosalicylate anion and water molecule are hydrogen bonded through N-H...O, N-H...N, N-H...OW and OW-HW...O hydrogen bonds, forming a large ring motif [R1010(56)], leading to a three-dimensional supramolecular network. In compound (III), 2-amino-4-chloro-6-methylpyrimidine (ACP) interacts with the carboxylic acid group of 6-chloronicotinic acid via N-H...O and O-H...O hydrogen bonds, generating an R22(8) primary ring motif. Furthermore, the ACP molecules form a base pair via N-H...N hydrogen bonds. The primary motif and base pair combine to form tetrameric units, which are further connected by Cl...Cl interactions. In addition to this hydrogen-bonding interaction, compounds (I) and (III) are further enriched by π-π stacking interactions.
期刊介绍：
Acta Crystallographica Section C: Structural Chemistry is continuing its transition to a journal that publishes exciting science with structural content, in particular, important results relating to the chemical sciences. Section C is the journal of choice for the rapid publication of articles that highlight interesting research facilitated by the determination, calculation or analysis of structures of any type, other than macromolecular structures. Articles that emphasize the science and the outcomes that were enabled by the study are particularly welcomed. Authors are encouraged to include mainstream science in their papers, thereby producing manuscripts that are substantial scientific well-rounded contributions that appeal to a broad community of readers and increase the profile of the authors.
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