Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties
Ciprofloxacin (CfH, C17H18FN3O3) crystallizes with 2‐thiobarbituric (H2tba) and barbituric acid (H2ba) in the aqueous solution to yield salt CfH2(Htba)·3H2O (1), salt cocrystal CfH2(Hba)(H2ba)·3H2O (2), and salt CfH2(Hba)·H2O (3). The compounds are structurally characterized by the X‐ray single‐crys...
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| Veröffentlicht in: | Journal of physical organic chemistry 2018-03, Vol.31 (3), p.n/a |
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| creator | Golovnev, Nicolay N. Molokeev, Maxim S. Lesnikov, Maxim K. Atuchin, Victor V. |
| description | Ciprofloxacin (CfH, C17H18FN3O3) crystallizes with 2‐thiobarbituric (H2tba) and barbituric acid (H2ba) in the aqueous solution to yield salt CfH2(Htba)·3H2O (1), salt cocrystal CfH2(Hba)(H2ba)·3H2O (2), and salt CfH2(Hba)·H2O (3). The compounds are structurally characterized by the X‐ray single‐crystal diffraction. The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba−/Hba− and CfH2+ ions, and H2ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2. There are different π‐π interactions in 1 to 3. The compounds have been characterized by powder X‐ray diffraction, thermogravimetry/differential scanning calorimetry, and Fourier transform infrared spectroscopy. The compounds dehydration ends at 130°C to 150°C, and their oxidative decomposition is observed in the range of 250°C to 275°C.
Ciprofloxacin (C17H18FN3O3) crystallizes with 2‐thiobarbituric and barbituric acid in the aqueous solution to yield salt CfH2(Htba)·3H2O (1), salt cocrystal CfH2(Hba)(H2ba)·3H2O (2), and salt CfH2(Hba)·H2O (3). The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba−/Hba− and CfH2+ ions, and H2ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2. |
| doi_str_mv | 10.1002/poc.3773 |
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Ciprofloxacin (C17H18FN3O3) crystallizes with 2‐thiobarbituric and barbituric acid in the aqueous solution to yield salt CfH2(Htba)·3H2O (1), salt cocrystal CfH2(Hba)(H2ba)·3H2O (2), and salt CfH2(Hba)·H2O (3). The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba−/Hba− and CfH2+ ions, and H2ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2.</description><identifier>ISSN: 0894-3230</identifier><identifier>EISSN: 1099-1395</identifier><identifier>DOI: 10.1002/poc.3773</identifier><language>eng</language><publisher>Bognor Regis: Wiley Subscription Services, Inc</publisher><subject>barbituric and thiobarbituric acids ; Chemical bonds ; ciprofloxacin ; Crystal structure ; Dehydration ; Diffraction ; Fourier transforms ; Hydrogen bonds ; infrared spectroscopy ; salt cocrystal ; thermal stability ; Thermogravimetry ; Water chemistry ; X‐ray diffraction</subject><ispartof>Journal of physical organic chemistry, 2018-03, Vol.31 (3), p.n/a</ispartof><rights>Copyright © 2017 John Wiley & Sons, Ltd.</rights><rights>Copyright © 2018 John Wiley & Sons, Ltd.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3273-36e3f21114568e828e013fcf14e60339891b5167c47309598e76f1c90891bab33</citedby><cites>FETCH-LOGICAL-c3273-36e3f21114568e828e013fcf14e60339891b5167c47309598e76f1c90891bab33</cites><orcidid>0000-0002-0951-5276 ; 0000-0002-9507-3709 ; 0000-0002-8297-0945 ; 0000-0002-7424-5604</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fpoc.3773$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fpoc.3773$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Golovnev, Nicolay N.</creatorcontrib><creatorcontrib>Molokeev, Maxim S.</creatorcontrib><creatorcontrib>Lesnikov, Maxim K.</creatorcontrib><creatorcontrib>Atuchin, Victor V.</creatorcontrib><title>Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties</title><title>Journal of physical organic chemistry</title><description>Ciprofloxacin (CfH, C17H18FN3O3) crystallizes with 2‐thiobarbituric (H2tba) and barbituric acid (H2ba) in the aqueous solution to yield salt CfH2(Htba)·3H2O (1), salt cocrystal CfH2(Hba)(H2ba)·3H2O (2), and salt CfH2(Hba)·H2O (3). The compounds are structurally characterized by the X‐ray single‐crystal diffraction. The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba−/Hba− and CfH2+ ions, and H2ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2. There are different π‐π interactions in 1 to 3. The compounds have been characterized by powder X‐ray diffraction, thermogravimetry/differential scanning calorimetry, and Fourier transform infrared spectroscopy. The compounds dehydration ends at 130°C to 150°C, and their oxidative decomposition is observed in the range of 250°C to 275°C.
Ciprofloxacin (C17H18FN3O3) crystallizes with 2‐thiobarbituric and barbituric acid in the aqueous solution to yield salt CfH2(Htba)·3H2O (1), salt cocrystal CfH2(Hba)(H2ba)·3H2O (2), and salt CfH2(Hba)·H2O (3). The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba−/Hba− and CfH2+ ions, and H2ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2.</description><subject>barbituric and thiobarbituric acids</subject><subject>Chemical bonds</subject><subject>ciprofloxacin</subject><subject>Crystal structure</subject><subject>Dehydration</subject><subject>Diffraction</subject><subject>Fourier transforms</subject><subject>Hydrogen bonds</subject><subject>infrared spectroscopy</subject><subject>salt cocrystal</subject><subject>thermal stability</subject><subject>Thermogravimetry</subject><subject>Water chemistry</subject><subject>X‐ray diffraction</subject><issn>0894-3230</issn><issn>1099-1395</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNp1kE9LAzEQxYMoWKvgRwh48bJ1stnNbrxJ8R8U6qGeQzZNaMrarEmWtt_e7NaDF0_Dm_ebN_AQuiUwIwD5Q-fUjFYVPUMTApxnhPLyHE2g5kVGcwqX6CqELUDyymqCDqu9w0G2MWC5W-O40aPCyil_DFG22BmsbOedad1BKrvDexs3CbSukb6xsfdWjbd_pbLr8IhXQ1r0vUpbPTIpp9M-Wh2u0YWRbdA3v3OKPl-eV_O3bLF8fZ8_LTJF84pmlGlqckJIUbJa13mtgVCjDCk0A0p5zUlTElapoqLAS17rihmiOAyGbCidortTbnr93esQxdb1fpdeihyAcQY1KxJ1f6KUdyF4bUTn7Zf0R0FADL2K1KsYek1odkL3ttXHfznxsZyP_A-yJHnH</recordid><startdate>201803</startdate><enddate>201803</enddate><creator>Golovnev, Nicolay N.</creator><creator>Molokeev, Maxim S.</creator><creator>Lesnikov, Maxim K.</creator><creator>Atuchin, Victor V.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-0951-5276</orcidid><orcidid>https://orcid.org/0000-0002-9507-3709</orcidid><orcidid>https://orcid.org/0000-0002-8297-0945</orcidid><orcidid>https://orcid.org/0000-0002-7424-5604</orcidid></search><sort><creationdate>201803</creationdate><title>Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties</title><author>Golovnev, Nicolay N. ; Molokeev, Maxim S. ; Lesnikov, Maxim K. ; Atuchin, Victor V.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3273-36e3f21114568e828e013fcf14e60339891b5167c47309598e76f1c90891bab33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>barbituric and thiobarbituric acids</topic><topic>Chemical bonds</topic><topic>ciprofloxacin</topic><topic>Crystal structure</topic><topic>Dehydration</topic><topic>Diffraction</topic><topic>Fourier transforms</topic><topic>Hydrogen bonds</topic><topic>infrared spectroscopy</topic><topic>salt cocrystal</topic><topic>thermal stability</topic><topic>Thermogravimetry</topic><topic>Water chemistry</topic><topic>X‐ray diffraction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Golovnev, Nicolay N.</creatorcontrib><creatorcontrib>Molokeev, Maxim S.</creatorcontrib><creatorcontrib>Lesnikov, Maxim K.</creatorcontrib><creatorcontrib>Atuchin, Victor V.</creatorcontrib><collection>CrossRef</collection><jtitle>Journal of physical organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Golovnev, Nicolay N.</au><au>Molokeev, Maxim S.</au><au>Lesnikov, Maxim K.</au><au>Atuchin, Victor V.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties</atitle><jtitle>Journal of physical organic chemistry</jtitle><date>2018-03</date><risdate>2018</risdate><volume>31</volume><issue>3</issue><epage>n/a</epage><issn>0894-3230</issn><eissn>1099-1395</eissn><abstract>Ciprofloxacin (CfH, C17H18FN3O3) crystallizes with 2‐thiobarbituric (H2tba) and barbituric acid (H2ba) in the aqueous solution to yield salt CfH2(Htba)·3H2O (1), salt cocrystal CfH2(Hba)(H2ba)·3H2O (2), and salt CfH2(Hba)·H2O (3). The compounds are structurally characterized by the X‐ray single‐crystal diffraction. The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba−/Hba− and CfH2+ ions, and H2ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2. There are different π‐π interactions in 1 to 3. The compounds have been characterized by powder X‐ray diffraction, thermogravimetry/differential scanning calorimetry, and Fourier transform infrared spectroscopy. The compounds dehydration ends at 130°C to 150°C, and their oxidative decomposition is observed in the range of 250°C to 275°C.
Ciprofloxacin (C17H18FN3O3) crystallizes with 2‐thiobarbituric and barbituric acid in the aqueous solution to yield salt CfH2(Htba)·3H2O (1), salt cocrystal CfH2(Hba)(H2ba)·3H2O (2), and salt CfH2(Hba)·H2O (3). The numerous intermolecular hydrogen bonds N–H⋯O and O–H⋯O formed by water molecules, Htba−/Hba− and CfH2+ ions, and H2ba molecules stabilize the crystal structures of 1 to 3. Hydrogen bonds form a 2D plane network in the salts of 1 and 3 and a 3D network in the salt cocrystal of 2.</abstract><cop>Bognor Regis</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/poc.3773</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-0951-5276</orcidid><orcidid>https://orcid.org/0000-0002-9507-3709</orcidid><orcidid>https://orcid.org/0000-0002-8297-0945</orcidid><orcidid>https://orcid.org/0000-0002-7424-5604</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | barbituric and thiobarbituric acids Chemical bonds ciprofloxacin Crystal structure Dehydration Diffraction Fourier transforms Hydrogen bonds infrared spectroscopy salt cocrystal thermal stability Thermogravimetry Water chemistry X‐ray diffraction |
| title | Two salts and the salt cocrystal of ciprofloxacin with thiobarbituric and barbituric acids: The structure and properties |
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