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The six halogen derivatives crystallise in the <jats:italic>monoclinic<\/jats:italic> group <jats:italic>P<\/jats:italic>2<jats:sub>1<\/jats:sub>\/<jats:italic>c<\/jats:italic>. In each case, the asymmetric unit is one half of the molecule, with the molecules lying across inversion centres, midway between the N\u2013N bonds, with the central C\u2013C=N\u2013N=C\u2013C fragments having all transoid conformations. Each of the six molecules deviates a little from overall planarity. The \u03c0\u00b7\u00b7\u00b7\u03c0 stacking interactions are the most important intermolecular interactions in each of the six compounds. In the cases of <jats:bold>3<\/jats:bold> and <jats:bold>4<\/jats:bold>, the \u03c0\u00b7\u00b7\u00b7\u03c0 stacks are augmented by additional C\u2013X\u00b7\u00b7\u00b7\u03c0 (X=Cl or Br) interactions, while in <jats:bold>4<\/jats:bold>, the \u03c0\u00b7\u00b7\u00b7\u03c0 stacks are linked by weak Br\u00b7\u00b7\u00b7Br interactions, and in <jats:bold>3<\/jats:bold>, weak Cl\u00b7\u00b7\u00b7Cl contacts are considered to be also involved in cementing the supra molecular arrangements. The short separations of the layers within the stacks and the extent of the overlaps of the \u03c0 systems point to significant strengths of the \u03c0\u00b7\u00b7\u00b7\u03c0 interactions. Comparisons with published structures of related chloro and fluoro compounds indicated similar results: related iodo derivatives, IC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>CH=N\u2013N=CHC<jats:sub>6<\/jats:sub>H<jats:sub>4<\/jats:sub>I do not possess as strong \u03c0\u00b7\u00b7\u00b7\u03c0 interactions. The Hirshfeld analysis indicated further intermolecular contacts which fell outside the normal PLATON cutoff values.<\/jats:p>","DOI":"10.1515\/zkri-2017-2081","type":"journal-article","created":{"date-parts":[[2018,1,28]],"date-time":"2018-01-28T10:02:30Z","timestamp":1517133750000},"page":"135-143","source":"Crossref","is-referenced-by-count":1,"title":["Crystal structures and Hirshfeld surface analyses of halogen substituted azine derivatives, 1,4-bis(halophenyl)-2,3-diazabuta-1,3-dienes"],"prefix":"10.1515","volume":"233","author":[{"given":"Nathasha R.","family":"de L Correira","sequence":"first","affiliation":[{"name":"FioCruz-Funda\u00e7\u00e3o Oswaldo Cruz, Instituto de Tecnologia em F\u00e1rmacos-Far-Manguinhos , Rua Sizenando Nabuco, 100, Manguinhos , 21041-250 Rio de Janeiro, RJ , Brazil"}]},{"given":"Thais C.M.","family":"Noguiera","sequence":"additional","affiliation":[{"name":"FioCruz-Funda\u00e7\u00e3o Oswaldo Cruz, Instituto de Tecnologia em F\u00e1rmacos-Far-Manguinhos , Rua Sizenando Nabuco, 100, Manguinhos , 21041-250 Rio de Janeiro, RJ , Brazil"}]},{"given":"Alessandra C.","family":"Pinheiro","sequence":"additional","affiliation":[{"name":"FioCruz-Funda\u00e7\u00e3o Oswaldo Cruz, Instituto de Tecnologia em F\u00e1rmacos-Far-Manguinhos , Rua Sizenando Nabuco, 100, Manguinhos , 21041-250 Rio de Janeiro, RJ , Brazil"}]},{"given":"Marcus V.N.","family":"de Souza","sequence":"additional","affiliation":[{"name":"FioCruz-Funda\u00e7\u00e3o Oswaldo Cruz, Instituto de Tecnologia em F\u00e1rmacos-Far-Manguinhos , Rua Sizenando Nabuco, 100, Manguinhos , 21041-250 Rio de Janeiro, RJ , Brazil"}]},{"given":"Ligia R.","family":"Gomes","sequence":"additional","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 , Old Aberdeen, AB24 3UE , Scotland , UK"}]},{"given":"James L.","family":"Wardell","sequence":"additional","affiliation":[{"name":"FioCruz-Funda\u00e7\u00e3o Oswaldo Cruz, Instituto de Tecnologia em F\u00e1rmacos-Far-Manguinhos , Rua Sizenando Nabuco, 100, Manguinhos , 21041-250 Rio de Janeiro, RJ , Brazil"},{"name":"Department of Chemistry , University of Aberdeen , Old Aberdeen, AB24 3UE , Scotland , UK"}]},{"given":"Solange M.S.V.","family":"Wardell","sequence":"additional","affiliation":[{"name":"CHEMSOL , 1 Harcourt Road, Aberdeen AB15 5NY , Scotland , UK"}]}],"member":"374","published-online":{"date-parts":[[2017,10,18]]},"reference":[{"key":"2022033122370585905_j_zkri-2017-2081_ref_001_w2aab3b7c36b1b6b1ab2b1b1Aa","doi-asserted-by":"crossref","unstructured":"J. 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