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The strong classical O\u2013H\u2009\u00b7\u2009\u00b7\u2009\u00b7\u2009N hydrogen bonds involving the oxime group generate C(3) chains in compound <jats:bold>1<\/jats:bold>, in contrast to the R<jats:sup>2<\/jats:sup>\n                  <jats:sub>2<\/jats:sub>(6) dimers formed in compounds <jats:bold>2\u20134<\/jats:bold>; such arrangements have been shown to be the most frequently found for oximes other than salicylaldoximes (2-hydroxybenzaldehyde oximes). In general, weaker intermolecular interactions involving the X substituents, as well as C\u2013H\u2009\u00b7\u2009\u00b7\u2009\u00b7\u2009O and \u03c0\u2009\u00b7\u2009\u00b7\u2009\u00b7\u2009\u03c0 interactions have significant effects on the supramolecular arrays generated in the aggegation. A further important interaction in compound <jats:bold>1<\/jats:bold>, and to a lesser extent in compound <jats:bold>4<\/jats:bold>, is a \u03c0(C=N)\u2009\u00b7\u2009\u00b7\u2009\u00b7\u2009\u03c0(phenyl) molecular stacking. A data base search has indicated that short Cg(C=N)\u2009\u00b7\u2009\u00b7\u2009\u00b7\u2009Cg(phenyl) distances, &lt;3.3 \u00c5 (Cg\u2009=\u2009centre of gravity), have been found in various compounds, including other oximes. A theoretical study was carried out starting from the crystal structure data of compound <jats:bold>1<\/jats:bold>, with optimisation at the BLYP-D3\/def2-DZVP level, as well as at the higher PBE0\/ma-def2-TZVP level. Breakdown of the interaction energy into separate contributions was achieved using SAPT (using the jun-cc-pvdz basis set). Overall, the calculations indicate that the \u03c0(C=N) \u00b7\u00b7\u2009\u00b7\u2009\u03c0(phenyl) interaction is attractive, with a magnitude of 14\u201318 kJ mol<jats:sup>\u22121<\/jats:sup>.<\/jats:p>","DOI":"10.1515\/znb-2018-0222","type":"journal-article","created":{"date-parts":[[2019,3,30]],"date-time":"2019-03-30T20:25:40Z","timestamp":1553977540000},"page":"319-334","source":"Crossref","is-referenced-by-count":5,"title":["Different substituent effects on the supramolecular arrays in some (<i>E<\/i>)-halo- and nitro-benzaldehyde oximes: confirmation of attractive \u03c0(C=N)\u00b7\u00b7\u00b7\u03c0(phenyl) interactions"],"prefix":"10.1515","volume":"74","author":[{"given":"Ligia R.","family":"Gomes","sequence":"first","affiliation":[{"name":"FP-ENAS-Faculdade de Ci\u00eancias de Sa\u00fade, Escola Superior de Sa\u00fade da UFP , Universidade Fernando Pessoa , Rua Carlos da Maia, 296 , P-4200-150 Porto , Portugal"},{"name":"REQUIMTE, Departamento de Qu\u00edmica e Bioqu\u00edmica , Faculdade de Ci\u00eancias da, Universidade do Porto , Rua do Campo Alegre, 687 , P-4169-007 Porto , Portugal"}]},{"given":"John N.","family":"Low","sequence":"additional","affiliation":[{"name":"Department of Chemistry , University of Aberdeen , Meston Walk, Old Aberdeen , AB24 3UE, Scotland , UK"}]},{"given":"Tanja","family":"van Mourik","sequence":"additional","affiliation":[{"name":"School of Chemistry , University of St. Andrews , North Haugh, St. Andrews , Fife KY16 9ST, Scotland , UK"}]},{"given":"Herbert","family":"Fr\u00fcchtl","sequence":"additional","affiliation":[{"name":"School of Chemistry , University of St. Andrews , North Haugh, St. Andrews , Fife KY16 9ST, Scotland , UK"}]},{"given":"Marcus V.N.","family":"de Souza","sequence":"additional","affiliation":[{"name":"Instituto de Tecnologia em F\u00e1rmacos e Farmanguinhos, Funda\u00e7\u00e3o Oswaldo Cruz , 21041-250 Rio de Janeiro, RJ , Brazil"}]},{"given":"Cristiane F.","family":"da Costa","sequence":"additional","affiliation":[{"name":"Instituto de Tecnologia em F\u00e1rmacos e Farmanguinhos, Funda\u00e7\u00e3o Oswaldo Cruz , 21041-250 Rio de Janeiro, RJ , Brazil"}]},{"given":"James L.","family":"Wardell","sequence":"additional","affiliation":[{"name":"Department of Chemistry , University of Aberdeen , Meston Walk, Old Aberdeen , AB24 3UE, Scotland , UK"},{"name":"Instituto de Tecnologia em F\u00e1rmacos e Farmanguinhos, Funda\u00e7\u00e3o Oswaldo Cruz , 21041-250 Rio de Janeiro, RJ , Brazil"}]}],"member":"374","published-online":{"date-parts":[[2019,4,2]]},"reference":[{"key":"2025041407314313662_j_znb-2018-0222_ref_001_w2aab3b7c75b1b6b1ab2b1b1Aa","doi-asserted-by":"crossref","unstructured":"E. 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