A 1:2 co-crystal of 2,2′-dithiodibenzoic acid and benzoic acid: crystal structure, Hirshfeld surface analysis and computational study

Abstract

The asymmetric unit of the title 1:2 co-crystal has a half mol­ecule of twofold symmetric di­thiodi­benzoic acid and a full mol­ecule of benzoic acid. These are connected into three-mol­ecule aggregates via hy­droxy-O—H⋯O(hy­droxy) hydrogen bonds.

Crystal structure of hemikis(cyclohexane-1,4-diammonium) (pyridine-2-carboxylate), [C6H16N2]0.5[C6H4NO2]

“…To the best of our knowledge, no reports on cocrystals of these Schiff base molecules exist. Recent studies of co-crystals designed to incorporate n-mercaptobenzoic acid as a conformer [10,11] resulted in unexpected outcomes, e.g. oxidation of the thiol, a well known phenomenon for n-mercaptobenzoic acids [12], and desulfurization [13], again observed previously [14].…”

Structural systematics in isomorphous binary co-crystal solvates comprising 2,2′-dithiodibenzoic acid, 4-halobenzoic acid and dimethylformamide (1 : 1 : 1), for halide = chloride, bromide and iodide

“…As expected, the eight-membered {⋯HOCO} 2 synthon resulting from the interaction between DTBA and 4- X BA gives rise to the most stable interaction energies with E interaction in the range of −70.9 to −73.2 kJ mol −1 ; these results are consistent with E interaction values of −69.8 to −73.2 kJ mol −1 obtained for some closely related analogues. 10,12,18 The most stable synthon is found in 3 and correlated with the influence of the less electronegative iodide atom. The next most stable synthon is the interaction between DTBA and DMF through the {⋯OCO⋯OCOH} heterosynthon, with a narrow range of E interaction values (−58.9 to −59.9 kJ mol −1 ).…”

“…Thus, the 1 : 1 co-crystallisation (DMF/toluene) of 2-MBA with benzoic acid (BA) gives rise to the anticipated three-molecule aggregate, BA⋯DTBA⋯BA, mediated by dissymmetric {⋯HOCO} 2 synthons. 18 An analogous experiment where BA was substituted by 2-chlorobenzoic acid (2-ClBA) yielded a different three-molecule aggregate formulated as 2-ClBA⋯DTBA⋯DMF, featuring one dissymmetric {⋯HOCO} 2 synthon and one {⋯HCO⋯HOCO} heterosynthon. 12 When 3-BrBA was employed and toluene was substituted by benzene, a supramolecular chain {DTBA} n was formed mediated by symmetric {⋯HOCO} 2 synthons, as were centrosymmetric dimers, {3-BrBA} 2 , again mediated by symmetric {⋯HOCO} 2 synthons.…”

Microcrystalline solid–solid transformations of conformationally-responsive solvates, desolvates and a salt of N,N′-(1,4-phenylene)dioxalamic acid: the energetics of hydrogen bonding and n/π → π* interactions

“…Nevertheless, the E tot values of the hetero R 2 2 (n) n = 7, 8 are larger than those reported for other hetero R 2 2 (7) involving O–H⋯N(py) HB (−49.4 to −52.0 kJ mol −1 range) 45 but smaller than the reported value for homo R 2 2 (8) in carboxylic acids (−73.0 kJ mol −1 ). 46…”

“…The Hirshfeld surfaces (HSs) of H 2 pOx•2S, mapped over the d norm (range 0.4 Å to 3.0 Å), are shown in 45 but smaller than the reported value for homo R 2 2 (8) in carboxylic acids (−73.0 kJ mol −1 ). 46 In addition, the amide N-H⋯O HB motif is the first directing energy contributor to the framework of the (HDMA) 2 pOx salt, the second in H 2 (10) with E tot = −61.9 kJ mol −1 , in benzylic oxalamides. 7 In both DMSO and DMF solvates, the third largest contributor to the E The nature of the attractive energy involved in O-H⋯O HB motifs, as the dominant interaction, is mainly electrostatic with a mean percent contribution to the stabilization energy (%E ele ) value of 73(±3)%, Table 1.…”