Structural Studies on Chemical Models of Enzymatic Catalysis: 2-Acetoxy-3-methylbenzoic Acid

Article abstract of DOI:10.1107/S0567740881006729

C10H10O4, monoclinic, P2₁/c, a=4.910 (1), b=11.702 (2), c=17.233 (6) Angstroem, β=98.36 (2) deg, Z=4, d_c=1.317 (1) Mg m^-3, R=0.032 for 615 observed data measured by diffractometer.The carboxyl group is twisted by 11.9 (6) deg out of the plane of the aromatic ring, and the acetoxy group is also twisted out of plane by 85.5 (5) deg.The ester oxygen atom O(3) lies out of plane of the aromatic ring by 0.17 (1) Angstroem.The carboxyl group is oriented such that its shorter C-O bond is syn to the acetoxy group, unlike aspirin in which it is anti.The molecule forms dimers with linear, asymmetric hydrogen bonds having O...O 2.627 (3) Angstroem.