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
Publication statusPublished - 2000 Aug

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Hydrogen
Crystals
Acrylamide
Hydrogen bonds
Mercury
Single crystals
hydrogen bonds
crystals
Mercury vapor lamps
mercury lamps
single crystals
Bandpass filters
bandpass filters
Pressure
Dimers
ribbons
dimers
Population
filters
Molecules

ASJC Scopus subject areas

  • Structural Biology
  • Condensed Matter Physics

Cite this

Crystal-to-crystal photodimerization of trans-cinnamamides. / Hosomi, Hiroyuki; Ito, Yoshikatsu; Ohba, Shigeru.

In: Acta Crystallographica Section B: Structural Science, Vol. 56, No. 4, 08.2000, p. 682-689.

Research output: Contribution to journalArticle

Hosomi, Hiroyuki ; Ito, Yoshikatsu ; Ohba, Shigeru. / Crystal-to-crystal photodimerization of trans-cinnamamides. In: Acta Crystallographica Section B: Structural Science. 2000 ; Vol. 56, No. 4. pp. 682-689.
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