{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,7,30]],"date-time":"2026-07-30T15:39:51Z","timestamp":1785425991109,"version":"3.56.0"},"reference-count":39,"publisher":"International Union of Crystallography (IUCr)","issue":"8","license":[{"start":{"date-parts":[[2024,7,19]],"date-time":"2024-07-19T00:00:00Z","timestamp":1721347200000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2024,7,19]],"date-time":"2024-07-19T00:00:00Z","timestamp":1721347200000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"NSF","award":["DMR-2122108"],"award-info":[{"award-number":["DMR-2122108"]}]},{"DOI":"10.13039\/100000001","name":"National Science Foundation","doi-asserted-by":"publisher","award":["DMR-1933487"],"award-info":[{"award-number":["DMR-1933487"]}],"id":[{"id":"10.13039\/100000001","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["iucr.org","wiley.com","iucrj.org"],"crossmark-restriction":true},"short-container-title":["Acta Crystallogr E Cryst Commun","Acta Cryst E","Acta Cryst Sect E","Acta Crystallogr E","Acta Crystallogr Sect E","Acta Cryst E Cryst Commun","Acta Cryst Sect E Cryst Commun"],"accepted":{"date-parts":[[2024,7,11]]},"published-print":{"date-parts":[[2024,8,1]]},"abstract":"<jats:p>\n                    The crystal structures of two intermediates, 4-amino-3,5-difluorobenzonitrile, C\n                    <jats:sub>7<\/jats:sub>\n                    H\n                    <jats:sub>4<\/jats:sub>\n                    F\n                    <jats:sub>2<\/jats:sub>\n                    N\n                    <jats:sub>2<\/jats:sub>\n                    (\n                    <jats:bold>I<\/jats:bold>\n                    ), and ethyl 4-amino-3,5-difluorobenzoate, C\n                    <jats:sub>9<\/jats:sub>\n                    H\n                    <jats:sub>9<\/jats:sub>\n                    F\n                    <jats:sub>2<\/jats:sub>\n                    NO\n                    <jats:sub>2<\/jats:sub>\n                    (\n                    <jats:bold>II<\/jats:bold>\n                    ), along with a visible-light-responsive azobenzene derivative, diethyl 4,4\u2032-(diazene-1,2-diyl)bis(3,5-difluorobenzoate), C\n                    <jats:sub>18<\/jats:sub>\n                    H\n                    <jats:sub>14<\/jats:sub>\n                    F\n                    <jats:sub>4<\/jats:sub>\n                    N\n                    <jats:sub>2<\/jats:sub>\n                    O\n                    <jats:sub>4<\/jats:sub>\n                    (\n                    <jats:bold>III<\/jats:bold>\n                    ), obtained by four-step synthetic procedure, were studied using single-crystal X-ray diffraction. The molecules of\n                    <jats:bold>I<\/jats:bold>\n                    and\n                    <jats:bold>II<\/jats:bold>\n                    demonstrate the quinoid character of phenyl rings accompanied by the distortion of bond angles related to the presence of fluorine substituents in the 3 and 5 (\n                    <jats:italic>ortho<\/jats:italic>\n                    ) positions. In the crystals of\n                    <jats:bold>I<\/jats:bold>\n                    and\n                    <jats:bold>II<\/jats:bold>\n                    , the molecules are connected by N\u2014H...N, N\u2014H...F and N\u2014H...O hydrogen bonds, C\u2014H...F short contacts, and \u03c0-stacking interactions. In crystal of\n                    <jats:bold>III<\/jats:bold>\n                    , only stacking interactions between the molecules are found.\n                  <\/jats:p>","DOI":"10.1107\/s2056989024006819","type":"journal-article","created":{"date-parts":[[2024,7,19]],"date-time":"2024-07-19T03:35:36Z","timestamp":1721360136000},"page":"867-872","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Synthesis, molecular and crystal structures of 4-amino-3,5-difluorobenzonitrile, ethyl 4-amino-3,5-difluorobenzoate, and diethyl 4,4\u2032-(diazene-1,2-diyl)bis(3,5-difluorobenzoate)"],"prefix":"10.1107","volume":"80","author":[{"given":"Egor M.","family":"Novikov","sequence":"first","affiliation":[{"id":[{"id":"https:\/\/ror.org\/016tyxe19","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jesus","family":"Guillen Campos","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03taz7m60","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Javier","family":"Read de Alaniz","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/03taz7m60","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-2508-5368","authenticated-orcid":true,"given":"Marina S.","family":"Fonari","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7475-3206","authenticated-orcid":true,"given":"Tatiana V.","family":"Timofeeva","sequence":"additional","affiliation":[{"id":[{"id":"https:\/\/ror.org\/016tyxe19","id-type":"ROR","asserted-by":"publisher"}]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2024,7,19]]},"reference":[{"key":"jq2034_bb1","doi-asserted-by":"crossref","first-page":"14522","DOI":"10.1021\/jacs.0c05383","volume":"142","author":"Aggarwal","year":"2020","journal-title":"J. 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