%0 Generic
%A Manoj, K.
%A Gonnade, Rajesh G.
%A Bhadbhade, Mohan M.
%A Shashidhar, Mysore S.
%D 2006
%T Subtle Crossover from C−H···O to SO···CO Short Contacts in the
Association of Diastereomers of
2,4(6)-Di-O-benzoyl-6(4)-O-[(1S)-10-camphorsulfonyl]-myo-inositol
1,3,5-Orthoformate upon Formation of Pseudopolymorphs
%U https://acs.figshare.com/articles/dataset/Subtle_Crossover_from_C_H_O_to_S_O_C_O_Short_Contacts_in_the_Association_of_Diastereomers_of_2_4_6_Di_i_O_i_benzoyl_6_4_i_O_i_1_i_S_i_10_camphorsulfonyl_i_m_i_i_yo_i_inositol_1_3_5_Orthoformate_upon_Formation_of_Pseudopolymorphs/3077266
%R 10.1021/cg060127l.s002
%2 https://ndownloader.figshare.com/files/4783066
%K receptor proteins
%K electron count
%K host molecules
%K symmetry axes
%K Molecular association
%K nonplanar guests
%K Subtle Crossover
%K diastereomeric association
%K guest selectivity experiments
%K space groups P 21
%K solvated forms II
%K sulfonyl drugs
%K form III
%K guest inclusion
%X Diastereomers of 2,4(6)-di-O-benzoyl-6(4)-O-[(1S)-10-camphorsulfonyl]-myo-inositol 1,3,5-orthoformate associate
via weak interactions to form “head-to-head” dimers in their crystals. Molecular association through C−H···O short contacts do not
leave any void for the guest inclusion, while association through SO···CO bridging produces pseudopolymorphs. Three crystalline
modifications are observed for the title compound: form I, monoclinic P21, without any guest solvent, and solvated forms II and
III, that belong to monoclinic space groups P21 and C2, respectively. A majority of solvates, which include pyridine, dichloromethane,
benzene, tetrahydrofuran, and cyclohexanone as guests, belong to form III. All these guests have 2-fold symmetry axes (C2) with
their electron count within 40−62 electrons; guest selectivity experiments indicate that planar aromatic guests (pyridine, benzene)
bind better to the host molecules as compared to nonplanar guests (dioxane, cyclohexanone). The molecular packing that is created
thorough channels in the crystal (avoiding interpenetration of the layers) are of interest because of their potential application in
molecular separation by forming selective inclusions. The diastereomeric association via SO···CO dipolar short contacts, a
consistent feature observed in all the solvates, is thought to have relevance in the binding of sulfonyl drugs to the CO moieties of
the receptor proteins.
%I ACS Publications