A 1:2 co-crystal of 2,2'-thiodi-benzoic acid and tri-phenyl-phosphane oxide: crystal structure, Hirshfeld surface analysis and computational study.

ABSTRACT: The asymmetric unit of the title co-crystal, 2,2'-thiodi-benzoic acid-tri-phenyl-phosphane oxide (1/2), C14H10O4S·2C18H15OP, comprises two mol-ecules of 2,2'-thiodi-benzoic acid [TDBA; systematic name: 2-[(2-carb-oxy-phen-yl)sulfan-yl]benzoic acid] and four mol-ecules of tri-phenyl-phosphane oxide [TPPO; systematic name: (di-phenyl-phosphor-yl)benzene]. The two TDBA mol-ecules are twisted about their di-sulfide bonds and exhibit dihedral angles of 74.40?(5) and 72.58?(5)° between the planes through the two SC6H4 residues. The carb-oxy-lic acid groups are tilted out of the planes of the rings to which they are attached forming a range of CO2/C6 dihedral angles of 19.87?(6)-60.43?(8)°. Minor conformational changes are exhibited in the TPPO mol-ecules with the range of dihedral angles between phenyl rings being -2.1?(1) to -62.8?(1)°. In the mol-ecular packing, each TDBA acid mol-ecule bridges two TPPO mol-ecules via hy-droxy-O-H?O(oxide) hydrogen bonds to form two three-mol-ecule aggregates. These are connected into a three-dimensional architecture by TPPO-C-H?O(oxide, carbon-yl) and TDBA-C-H?(oxide, carbon-yl) inter-actions. The importance of H?H, O?H/H?O and C?H/H?C contacts to the calculated Hirshfeld surfaces has been demonstrated. In terms of individual mol-ecules, O?H/H?O contacts are more important for the TDBA (ca 28%) than for the TPPO mol-ecules (ca 13%), as expected from the chemical composition of these species. Computational chemistry indicates the four independent hy-droxy-O-H?O(oxide) hydrogen bonds in the crystal impart about the same energy (ca 52?kJ?mol-1), with DTBA-phenyl-C-H?O(oxide) inter-actions being next most stabilizing (ca 40?kJ?mol-1).

SUBMITTER: Tan SL 

PROVIDER: S-EPMC6281110 | biostudies-literature | 2018 Dec

REPOSITORIES: biostudies-literature