X-Ray Analysis of trans-9, 10-Dihydroxy-9,10-diphenyl-9,10-dihydroanthracene and Its 1:2 Molecular Complex with Methanol,and Structural Comparison with the Related 1:1 Ethanol and 1:1 1,4-Butanediol Adducts

trans-9,10-Dihydroxy-9,10-diphenyl-9,10-dihydroanthracene (2) and its 1:2 molecular complex (3) with methanol have been subjected to X-ray analysis. The crystal structure of 2 is built of discrete molecules held by π interactions between neighboring parallel phenyl rings and van der Waals forces, whereas that of 3 features virtually rhombic hydrogen-bonded (OH)₄ rings, each comprising two methanol fragments and two hydroxy groups, linking the molecular moieties into a chain-and-layer arrangement. The molecular stereochemistry, hydrogen bonding, and packing modes in these two compounds are compared with those in the 1:1 adducts of 2 with ethanol and 1,4-butanediol. Crystal data: for 2, space group P1, a = 6.814(1), b = 8.119(1), c = 9.053(1)Å, α = 103.66(1), β = 96.30(1), γ = 106.55(1)°, and Z = 1 : for 3, space group C2/c, a = 12.165(3), b = 12.484(3), c = 16.349(4)Å, β = 110.33(2)° and Z = 4. Based on observed MoKα data, the structures of 2 and 3 have been refined to R_F = 0.069 for 1139 reflections and R_F = 0.070 for 1412 reflections, respectively.