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Trimethyl citrate, C 9 H 14 O 7 (systematic name: trimethyl 2-hy-droxy-propane-1,2,3-tri-carboxyl-ate), 2 , was prepared by the esterification of citric acid and methanol in the presence of thionyl chloride at 273 K. The bond lengths and angles in 2 compare closely with those observed in citric acid. The C-C bonds adjacent to the terminal carboxyl groups are significantly shorter than those around the central C atom. The central carboxyl-ate group and the hy-droxy group occur in the normal planar arrangement with an r.m.s. deviation of 0.0171 Å from the mean plane involving all six atoms in the central unit. The crystal structure is almost completely dominated by the formation of inversion dimers through an O-H⋯O hydrogen bond, together with an extensive array of weaker C-H⋯O contacts. These generate a three-dimensional network structure with mol-ecules stacked along the c -axis direction.

Inversion dimers dominate the crystal packing in the structure of trimethyl citrate (trimethyl 2-hydroxypropane-1,2,3-tricarboxylate)