Abstract
Crystal and molecular structures for aryl- and benzyl-substituted 3-hydroxy-3,4-dihydroisobenzopyran-1-one are described. For the 4,4-dimethyl derivative, two monoclinic modifications are produced on sublimation: (1) P21/c, a = 23.668(6) Å b = 11.749(4) Å c = 7.215(2) Å β = 96.70(2)○; V = 1992.6(10) Å3; (2) P21/c, a = 11.509(4) Å, b = 12.429(4) Å, c = 6.933(2) Å, β = 91.12(3)○, V = 991.6(6) Å. In both, hydroxy groups are pseudoaxial, and molecules form dimeric complementary but noncooperative hydrogen bonds. In the 6-methoxy derivative (3), P21/c; a = 14.185(7) Å b = 4.105(4) Å c = 15.598(13) Å β = 98.59(6)○; V = 898.1(10) Å3, the hydroxy group is pseudoequatorial, and the intermolecular hydrogen bonding forms infinite chains. In the 4,4-dimethyl-7-nitro derivative (4), C2/c, a = 19.365(4), b = 8.425(2), c = 13.464(4), β = 92.62(2), V = 2194.2(7) Å3, the hydroxy group is pseudoaxial, and the intermolecular hydrogen bonding forms chains. Compared to the unmethylated compounds, the interbond angles within the ring at the dimethylated carbon are contracted.
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Cooper, W.J., Smith, T.N., Barker, A.K. et al. Pseudoacids. III: formation and structures of new cyclic oxocarboxylic acids. Journal of Chemical Crystallography 33, 375–384 (2003). https://doi.org/10.1023/A:1024226029750
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DOI: https://doi.org/10.1023/A:1024226029750