title: Structure of 3,4,5-trihydroxybenzoic acid octyl ester (octyl gallate) dihydrate at 123 K. A non-mesogenic amphiphilic molecule.
abstract: The crystal structure of 3,4,5-trihydroxybenzoic acid octyl ester (octyl gallate) dihydrate, C15H22O5.2H2O, is triclinic, P1, with a = 6.617 (1) [6.648 (1)], b = 9.956 (2) [9.995 (3)], c = 14.088 (4) [14.327 (7)] A, alpha = 79.08 (2) [79.78 (3)], beta = 85.58 (3) [86.59 (4)], gamma = 70.80 (2) [70.99 (3)] degrees, V = 860.5 A3, Z = 2, Dx = 1.229 1.229 [1.183] g cm-3, lambda(Mo K alpha) = 0.7093 A, mu = 0.58 cm-1, F(000) = 344 at 123 K [290 K]. The structure was solved by direct methods and refined to R(F2) = 0.059 for 302 parameters and 3655 observations. The alkyl chain of the molecule is in the fully extended conformation. The molecular packing is head-to-head bilayer with interdigitizing alkyl chains. The gallate head groups are hydrogen bonded with the water molecules to form a strong system of intra- and intermolecular hydrogen bonds consisting of finite and infinite chains. The crystals undergo crystal-to-crystal phase transitions at 365 K on heating and at 333 K on cooling, but despite the molecular packing which is analogous to that of the mesogenic alkyl glycosides, there is no thermotropic liquid crystal phase prior to the formation of the isotropic liquid phases at 376 K. Similary, no lyotropic liquid crystal phases are observed at room temperature in contact with a mixture of water and propanediol in which the crystals are soluble.
authors.affiliation: Department of Crystallography, university of Pittsburg, PA 15260.
authors.forename: G A
authors.initials: GA
authors.lastname: Jeffrey
authors.forename: Y
authors.initials: Y
authors.lastname: Yeon
mesh_terms: D002152:Calorimetry, Differential Scanning; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D003460:Crystallization; D003461:Crystallography; D005707:Gallic Acid / Q000031:analogs & derivatives* / Q000737:chemistry; D008961:Models, Structural; D008968:Molecular Conformation; D013816:Thermodynamics; D014961:X-Ray Diffraction
chemical_list: C016627:octyl gallate; D005707:Gallic Acid