A new polymorph of ortho-ethoxy-trans-cinnamic acid: single-to-single-crystal phase transformation and mechanism

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The α-polymorph of ortho-ethoxy-trans-cinnamic acid (OETCA) undergoes a reversible single-crystal-to-single-crystal phase transformation at 333 K. The new high-temperature polymorph (α′-OETCA) is stable between 333 and 393 K with three molecules in the asymmetric unit (Z′ = 3), space group P . Unlike the other polymorphs (and solvate) of OETCA recently reported, two of the molecules in α′-OETCA deviate significantly from planarity. This conformational change results in the corrugated sheet-type structure of α′-OETCA. The sheets are made up of ribbons, each composed of hydrogen-bonded pairs (via the —COOH groups), which are further connected by CH…O interactions. When exposed to UV radiation the α′-OETCA polymorph can be stabilized below 333 K with ca 8% of the monomer converted into the photodimer. The crystal structures of α′-OETCA are reported at two temperatures above the phase transition point (at 345 and 375 K) as well as the stabilized forms at 173 and 293 K. A mechanism for the phase transition involving a cooperative conformational transformation coupled with a shift of layers of OETCA molecules is proposed. The α′-OETCA polymorph is also an example of a cinnamic acid derivative where two different potentially photoreactive environments exist in one crystal in which each unit cell has two non-centrosymmetric predimer sites and one centrosymmetric predimer site.

Keywords: phase transformation and mechanism; photodimer; polymorph

Document Type: Research Article

DOI: http://dx.doi.org/10.1107/S0108768104009048

Publication date: June 1, 2004

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