Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies
A mixture of the E and Z isomers of ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate was synthesized and characterized by elemental analysis, attenuated total reflectance-Fourier transform infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopy. The structure of the Z isomer was de...
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| Veröffentlicht in: | Journal of molecular structure 2016-09, Vol.1120, p.333-340 |
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| creator | Matos, Catiúcia R.M.O. Vitorino, Letícia S. de Oliveira, Pedro H.R. de Souza, Maria Cecília B.V. Cunha, Anna C. Boechat, Fernanda da C.S. Resende, Jackson A.L.C. Carneiro, José Walkimar de M. Ronconi, Célia M. |
| description | A mixture of the E and Z isomers of ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate was synthesized and characterized by elemental analysis, attenuated total reflectance-Fourier transform infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopy. The structure of the Z isomer was determined by single crystal X-ray diffraction, which revealed a three-dimensional supramolecular network governed by CH⋯N, CH⋯O, and CH⋯F hydrogen bonds and π⋯π stacking interactions. The combination of these interactions plays an important role in stabilizing the self-assembly process and the molecular conformation. Hirshfeld surface analysis indicated the roles of the noncovalent interactions in the crystal packing, which were quantified by fingerprint plots and DFT calculations.
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•The (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate isomer was crystallized.•The extended network of the isomer was investigated.•Hirshfeld surface analysis and DFT studies of the extended network were carried out. |
| doi_str_mv | 10.1016/j.molstruc.2016.05.033 |
| format | Article |
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•The (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate isomer was crystallized.•The extended network of the isomer was investigated.•Hirshfeld surface analysis and DFT studies of the extended network were carried out.</description><identifier>ISSN: 0022-2860</identifier><identifier>EISSN: 1872-8014</identifier><identifier>DOI: 10.1016/j.molstruc.2016.05.033</identifier><language>eng</language><publisher>Elsevier B.V</publisher><subject>Acrylates ; Bonding ; Crystal structure ; DFT studies ; Ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate E and Z isomers ; Fingerprints ; Hirshfeld surface analysis ; Isomers ; Molecular structure ; Noncovalent interactions ; Self assembly ; Stacking ; Three dimensional</subject><ispartof>Journal of molecular structure, 2016-09, Vol.1120, p.333-340</ispartof><rights>2016 Elsevier B.V.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c345t-c534120da0e50d0febf05247a2043e636b3e5ce79d6fe6a08b6efc2524f2ac2e3</citedby><cites>FETCH-LOGICAL-c345t-c534120da0e50d0febf05247a2043e636b3e5ce79d6fe6a08b6efc2524f2ac2e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.molstruc.2016.05.033$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,777,781,3537,27905,27906,45976</link.rule.ids></links><search><creatorcontrib>Matos, Catiúcia R.M.O.</creatorcontrib><creatorcontrib>Vitorino, Letícia S.</creatorcontrib><creatorcontrib>de Oliveira, Pedro H.R.</creatorcontrib><creatorcontrib>de Souza, Maria Cecília B.V.</creatorcontrib><creatorcontrib>Cunha, Anna C.</creatorcontrib><creatorcontrib>Boechat, Fernanda da C.S.</creatorcontrib><creatorcontrib>Resende, Jackson A.L.C.</creatorcontrib><creatorcontrib>Carneiro, José Walkimar de M.</creatorcontrib><creatorcontrib>Ronconi, Célia M.</creatorcontrib><title>Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies</title><title>Journal of molecular structure</title><description>A mixture of the E and Z isomers of ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate was synthesized and characterized by elemental analysis, attenuated total reflectance-Fourier transform infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopy. The structure of the Z isomer was determined by single crystal X-ray diffraction, which revealed a three-dimensional supramolecular network governed by CH⋯N, CH⋯O, and CH⋯F hydrogen bonds and π⋯π stacking interactions. The combination of these interactions plays an important role in stabilizing the self-assembly process and the molecular conformation. Hirshfeld surface analysis indicated the roles of the noncovalent interactions in the crystal packing, which were quantified by fingerprint plots and DFT calculations.
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•The (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate isomer was crystallized.•The extended network of the isomer was investigated.•Hirshfeld surface analysis and DFT studies of the extended network were carried out.</description><subject>Acrylates</subject><subject>Bonding</subject><subject>Crystal structure</subject><subject>DFT studies</subject><subject>Ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate E and Z isomers</subject><subject>Fingerprints</subject><subject>Hirshfeld surface analysis</subject><subject>Isomers</subject><subject>Molecular structure</subject><subject>Noncovalent interactions</subject><subject>Self assembly</subject><subject>Stacking</subject><subject>Three dimensional</subject><issn>0022-2860</issn><issn>1872-8014</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNqFkc-KFDEQxhtRcFx9BclxBkxbSTo97U3ZdV1hwYPrxUvIpCtMhnRnTHWEfgmf2ayjZ0_1h-_7qOLXNK8FtAJE__bUTinSkotrZZ1b0C0o9aTZiGEv-QCie9psAKTkcujhefOC6AQAopo3za-v5ZxtDUBXos3MEuF0iCtLnm2_7zguxzUyyd1q58QV32477mNJOZ2POK9xZ6cwpx2zLq_RLviG1YYWG9mfi5aS6-ouZDp6jCOjkr11yOxs40qBajOym9uHqi5jQHrZPPM2Er76W6-ab7cfH67v-P2XT5-vP9xzpzq9cKdVJySMFlDDCB4PHrTs9lZCp7BX_UGhdrh_N_YeewvDoUfvZJV4aZ1EddVsL7nnnH4UpMVMgRzGaGdMhYwYpNbdIKSo0v4idTkRZfTmnMNk82oEmEcA5mT-ATCPAAxoUwFU4_uLEesjPwNmQy7g7HAMGd1ixhT-F_Eb29aUuA</recordid><startdate>20160915</startdate><enddate>20160915</enddate><creator>Matos, Catiúcia R.M.O.</creator><creator>Vitorino, Letícia S.</creator><creator>de Oliveira, Pedro H.R.</creator><creator>de Souza, Maria Cecília B.V.</creator><creator>Cunha, Anna C.</creator><creator>Boechat, Fernanda da C.S.</creator><creator>Resende, Jackson A.L.C.</creator><creator>Carneiro, José Walkimar de M.</creator><creator>Ronconi, Célia M.</creator><general>Elsevier B.V</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20160915</creationdate><title>Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies</title><author>Matos, Catiúcia R.M.O. ; Vitorino, Letícia S. ; de Oliveira, Pedro H.R. ; de Souza, Maria Cecília B.V. ; Cunha, Anna C. ; Boechat, Fernanda da C.S. ; Resende, Jackson A.L.C. ; Carneiro, José Walkimar de M. ; Ronconi, Célia M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c345t-c534120da0e50d0febf05247a2043e636b3e5ce79d6fe6a08b6efc2524f2ac2e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Acrylates</topic><topic>Bonding</topic><topic>Crystal structure</topic><topic>DFT studies</topic><topic>Ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate E and Z isomers</topic><topic>Fingerprints</topic><topic>Hirshfeld surface analysis</topic><topic>Isomers</topic><topic>Molecular structure</topic><topic>Noncovalent interactions</topic><topic>Self assembly</topic><topic>Stacking</topic><topic>Three dimensional</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Matos, Catiúcia R.M.O.</creatorcontrib><creatorcontrib>Vitorino, Letícia S.</creatorcontrib><creatorcontrib>de Oliveira, Pedro H.R.</creatorcontrib><creatorcontrib>de Souza, Maria Cecília B.V.</creatorcontrib><creatorcontrib>Cunha, Anna C.</creatorcontrib><creatorcontrib>Boechat, Fernanda da C.S.</creatorcontrib><creatorcontrib>Resende, Jackson A.L.C.</creatorcontrib><creatorcontrib>Carneiro, José Walkimar de M.</creatorcontrib><creatorcontrib>Ronconi, Célia M.</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Journal of molecular structure</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Matos, Catiúcia R.M.O.</au><au>Vitorino, Letícia S.</au><au>de Oliveira, Pedro H.R.</au><au>de Souza, Maria Cecília B.V.</au><au>Cunha, Anna C.</au><au>Boechat, Fernanda da C.S.</au><au>Resende, Jackson A.L.C.</au><au>Carneiro, José Walkimar de M.</au><au>Ronconi, Célia M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies</atitle><jtitle>Journal of molecular structure</jtitle><date>2016-09-15</date><risdate>2016</risdate><volume>1120</volume><spage>333</spage><epage>340</epage><pages>333-340</pages><issn>0022-2860</issn><eissn>1872-8014</eissn><abstract>A mixture of the E and Z isomers of ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate was synthesized and characterized by elemental analysis, attenuated total reflectance-Fourier transform infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopy. The structure of the Z isomer was determined by single crystal X-ray diffraction, which revealed a three-dimensional supramolecular network governed by CH⋯N, CH⋯O, and CH⋯F hydrogen bonds and π⋯π stacking interactions. The combination of these interactions plays an important role in stabilizing the self-assembly process and the molecular conformation. Hirshfeld surface analysis indicated the roles of the noncovalent interactions in the crystal packing, which were quantified by fingerprint plots and DFT calculations.
[Display omitted]
•The (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate isomer was crystallized.•The extended network of the isomer was investigated.•Hirshfeld surface analysis and DFT studies of the extended network were carried out.</abstract><pub>Elsevier B.V</pub><doi>10.1016/j.molstruc.2016.05.033</doi><tpages>8</tpages></addata></record> |
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| subjects | Acrylates Bonding Crystal structure DFT studies Ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate E and Z isomers Fingerprints Hirshfeld surface analysis Isomers Molecular structure Noncovalent interactions Self assembly Stacking Three dimensional |
| title | Supramolecular assembly of (Z)-ethyl 2-cyano-3-((4-fluorophenyl)amino) acrylate, crystal structure, Hirshfeld surface analysis and DFT studies |
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