Crystal-to-crystal photodimerization of trans-cinnamamides

Hiroyuki Hosomi, Yoshikatsu Ito, Shigeru Ohba

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

In the crystals of trans-4-methylcinnamamide, C10H11NO (I), trans-4-chlorocinnamamide, C9H8ClNO (II), trans-3-(2-thienyl)acrylamide, C7H7NOS (III), and trans-cinnamamide, C9H9NO (IV), the shortest intermolecular C⋯C distances between the C=C double bonds are 3.670 (2), 3.632 (2), 3.762 (3) and 4.120 (2) Å, respectively, for the pair of molecules related by a center of symmetry. The structure analysis was also carried out for trans-2-(p-chlorophenyl)-cis-4-(p-chlorophenyl)-1-trans-3-diamidocyclobutane, C18H16Cl2-N2O2 (V), which is the α-type photodimer of (II). The N -H⋯O hydrogen-bond networks in (I)-(III) are composed of two-dimensional pleated sheets, and those in (IV) and (V) of one-dimensional flat ribbons. The single crystals of (I), (II) and (IV) were photoirradiated with a 250 W ultra-high-pressure mercury lamp through a band-pass filter or a long-pass filter for 2-5 h. The photodimer was produced in each crystal with retention of the single-crystal form. The populations of the dimers were converged to 86.2 (4), 48.4 (6) and 4.5 (2)% in the refinement of the crystals after photoirradiation, (I′), (II′) and (IV′), respectively. Although the intermolecular N-H⋯O hydrogen-bond network remained in (I′) and (II′), the network was partly broken in (IV′) in the process of photoreaction.

Original languageEnglish
Pages (from-to)682-689
Number of pages8
JournalActa Crystallographica Section B: Structural Science
Volume56
Issue number4
DOIs
Publication statusPublished - 2000 Aug

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

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