{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,2]],"date-time":"2026-09-02T06:18:14Z","timestamp":1788329894222,"version":"build-2803163510"},"reference-count":30,"publisher":"International Union of Crystallography (IUCr)","issue":"6","license":[{"start":{"date-parts":[[2026,5,22]],"date-time":"2026-05-22T00:00:00Z","timestamp":1779408000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"},{"start":{"date-parts":[[2026,5,22]],"date-time":"2026-05-22T00:00:00Z","timestamp":1779408000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/legalcode"}],"funder":[{"name":"RUDN University Scientific Projects Grant System","award":["021422\u20132-000"],"award-info":[{"award-number":["021422\u20132-000"]}]},{"name":"Hacettepe University Scientific Research Project Unit","award":["013 D04 602 004"],"award-info":[{"award-number":["013 D04 602 004"]}]}],"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":[[2026,5,16]]},"published-print":{"date-parts":[[2026,6,1]]},"abstract":"<jats:p>\n                    The title compound, C\n                    <jats:sub>20<\/jats:sub>\n                    H\n                    <jats:sub>19<\/jats:sub>\n                    NO\n                    <jats:sub>3<\/jats:sub>\n                    , consists of a benzyl moiety bonded to the nitrogen atom of a 1\n                    <jats:italic>H<\/jats:italic>\n                    -benzo[\n                    <jats:italic>f<\/jats:italic>\n                    ]isoindole-4-carboxylic acid group. The fused pyrrole and cyclohexene rings of the isoindole group are in envelope and flattened-boat conformations, respectively. The planar benzene rings are oriented at a dihedral angle of 69.64\u2005(3)\u00b0. In the crystal, O\u2014H...O and C\u2014H...O hydrogen bonds link the molecules, enclosing\n                    <jats:italic>R<\/jats:italic>\n                    <jats:sup>2<\/jats:sup>\n                    <jats:sub>2<\/jats:sub>\n                    (14) and\n                    <jats:italic>R<\/jats:italic>\n                    <jats:sup>2<\/jats:sup>\n                    <jats:sub>2<\/jats:sub>\n                    (9) ring motifs, into infinite double-chains along the\n                    <jats:italic>a<\/jats:italic>\n                    -axis direction. \u03c0\u2013\u03c0 stacking interactions and C\u2014H...\u03c0(ring) interactions help to consolidate the packing. Hirshfeld surface analysis revealed that the most important contributions for the crystal packing are from H...H (52.2%), H...C\/C...H (24.0%) and H...O\/O...H (21.2%) interactions. The volume of the crystal voids and the percentage of free space were calculated to be 92.25\u2005\u00c5\n                    <jats:sup>3<\/jats:sup>\n                    and 11.52%, showing that there is no large cavity in the crystal packing. Computational methods revealed O\u2014H...O and C\u2014H...O hydrogen-bonding energies of \u2212103.8, \u221282.2 and \u221235.5\u2005kJ\u2005mol\n                    <jats:sup>\u22121<\/jats:sup>\n                    . Evaluations of the electrostatic, dispersion and total energy frameworks indicate that the stabilization is dominated by the electrostatic energy contributions.\n                  <\/jats:p>","DOI":"10.1107\/s2056989026005189","type":"journal-article","created":{"date-parts":[[2026,5,20]],"date-time":"2026-05-20T10:33:44Z","timestamp":1779273224000},"page":"722-727","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":0,"title":["Synthesis, crystal structure determination, Hirshfeld surface and crystal void analyses, interaction energy calculations and energy frameworks of (3a\n                    <i>RS<\/i>\n                    ,4\n                    <i>RS<\/i>\n                    ,9a\n                    <i>RS<\/i>\n                    )-2-benzyl-3-oxo-2,3,3a,4,9,9a-hexahydro-1\n                    <i>H<\/i>\n                    -benzo[\n                    <i>f<\/i>\n                    ]isoindole-4-carboxylic acid"],"prefix":"10.1107","volume":"82","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-6414-7122","authenticated-orcid":true,"given":"Kseniia A.","family":"Alekseeva","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8602-4382","authenticated-orcid":true,"given":"Tuncer","family":"H\u00f6kelek","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8806-2975","authenticated-orcid":true,"given":"Victor N.","family":"Khrustalev","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Maxim Y.","family":"Kolomeytsev","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Anastasia A.","family":"Pronina","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4175-5656","authenticated-orcid":true,"given":"Alebel N.","family":"Belay","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Khudayar I.","family":"Hasanov","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"329","published-online":{"date-parts":[[2026,5,22]]},"reference":[{"key":"yz2079_bb1","doi-asserted-by":"crossref","first-page":"40","DOI":"10.1107\/S2056989025010709","volume":"82","author":"Alekseeva","year":"2026","journal-title":"Acta Cryst. 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