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N<\/jats:italic>-(6-hydroxyhexyl)-3,4,5-trimethoxybenzamide, C<jats:sub>16<\/jats:sub>H<jats:sub>25<\/jats:sub>NO<jats:sub>5<\/jats:sub>, (<jats:bold>1<\/jats:bold>),<jats:italic>N<\/jats:italic>-(6-anilinohexyl)-3,4,5-trimethoxybenzamide, C<jats:sub>22<\/jats:sub>H<jats:sub>30<\/jats:sub>N<jats:sub>2<\/jats:sub>O<jats:sub>4<\/jats:sub>, (<jats:bold>2<\/jats:bold>), and<jats:italic>N<\/jats:italic>-(6,6-diethoxyhexyl)-3,4,5-trimethoxybenzamide, C<jats:sub>20<\/jats:sub>H<jats:sub>33<\/jats:sub>NO<jats:sub>6<\/jats:sub>, (<jats:bold>3<\/jats:bold>), are described. These compounds differ only in the substituent at the end of the hexyl chain and the nature of these substituents determines the differences in hydrogen bonding between the molecules. In each molecule, the<jats:italic>m<\/jats:italic>-methoxy substituents are virtually coplanar with the benzyl ring, while the<jats:italic>p<\/jats:italic>-methoxy substituent is almost perpendicular. The carbonyl O atom of the amide rotamer is<jats:italic>trans<\/jats:italic>related with the amidic H atom. In each structure, the benzamide N\u2014H donor group and O acceptor atoms link the molecules into<jats:italic>C<\/jats:italic>(4) chains. In<jats:bold>1<\/jats:bold>, a terminal \u2013OH group links the molecules into a<jats:italic>C<\/jats:italic>(3) chain and the combined effect of the<jats:italic>C<\/jats:italic>(4) and<jats:italic>C<\/jats:italic>(3) chains is a ribbon made up of screw related<jats:italic>R<\/jats:italic><jats:sub>2<\/jats:sub><jats:sup>2<\/jats:sup>(17) rings in which the ...O\u2014H... chain lies in the centre of the ribbon and the trimethoxybenzyl groups forms the edges. In<jats:bold>2<\/jats:bold>, the combination of the benzamide<jats:italic>C<\/jats:italic>(4) chain and the hydrogen bond formed by the terminal N\u2014H group to an O atom of the 4-methoxy group link the molecules into a chain of<jats:italic>R<\/jats:italic><jats:sub>2<\/jats:sub><jats:sup>2<\/jats:sup>(17) rings. In<jats:bold>3<\/jats:bold>, the molecules are linked only by<jats:italic>C<\/jats:italic>(4) chains.<\/jats:p>","DOI":"10.1107\/s2056989016005958","type":"journal-article","created":{"date-parts":[[2016,4,26]],"date-time":"2016-04-26T11:26:43Z","timestamp":1461670003000},"page":"675-682","update-policy":"https:\/\/doi.org\/10.1107\/cm_01","source":"Crossref","is-referenced-by-count":2,"title":["Crystal structures of three 3,4,5-trimethoxybenzamide-based derivatives"],"prefix":"10.1107","volume":"72","author":[{"given":"Ligia R.","family":"Gomes","sequence":"first","affiliation":[]},{"given":"John Nicolson","family":"Low","sequence":"additional","affiliation":[]},{"given":"Catarina","family":"Oliveira","sequence":"additional","affiliation":[]},{"given":"Fernando","family":"Cagide","sequence":"additional","affiliation":[]},{"given":"Fernanda","family":"Borges","sequence":"additional","affiliation":[]}],"member":"329","published-online":{"date-parts":[[2016,4,15]]},"reference":[{"unstructured":"Agilent (2014). 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