A comparison of X-ray crystal structures including methyl 3,5-bis(hydroxymethyl)benzoate, its phenylethynyl extended derivative in polymorphous forms and the corresponding carboxylic acids

Abstract

Considering the specific supramolecular synthon design of carboxylic acid and alcoholic hydroxyl groups in the field of crystal engineering, we compared the solid state structures of particular benzoates and corresponding acids 1-4 both in the non-spacered (1, 2) and spacered (3, 4) forms. Based on the single crystal X-ray study, there is only a slight influence of the phenylacetylene spacer with regard to the layer lattice arrangement of the benzoates while referring to the benzoic acid analogues the addition of the spacer gives rise to a modification of the lattice from a layer to a tape structure. Dependent on the crystallization conditions, two crystalline polymorphs of compound 3 (3a, 3b) were obtained and discussed regarding their structural differences.

On the origin of surfaces-dependent growth of benzoic acid crystal inferred through the droplet evaporation method

“…The control of crystallization is essential both from scientific and technological perspectives. Formation of biominerals, production of pharmaceuticals, supermolecular chemistry, semiconductors manufacturing, or designing materials for nonlinear optics or biomineralization are some of potential areas of interests [1][2][3]. Probably one of the most popular methods of crystallization is solution evaporation.…”

Attempted covalent imitation of a supramolecular synthon moiety embedded in a crystalline hydrogen-bonded aggregate structure

“…Instead, zigzag and straight type hydrogen bonded networks are created to afford sheet and ladder structures depending on the kind of additionally present alkoxy substituents. More recently, crystal structures of related compounds that lack the alkoxy groups and feature extended benzoic acid frameworks ( Figure 1) were also reported to show packing patterns as expected [20]. Thus, one may well say that carboxylic acid dimer formation including consequences on the crystal structure has proven largely reliable in supramolecular tecton behavior.…”

“…Structural characterization of solid 1 was performed applying the single crystal structure X-ray diffraction technique while the crystal structures of the benzoic acid derivatives 2-4 ( Figure 1) serving as the compounds of comparison in the present study are already known from previous works [19,20]. Relevant crystallographic data of 1 are summarized in Table 1.…”

Redetermination of tetramethyl tetrathiafulvalene-2,3,6,7-tetracarboxylate

“…For a previously reported experimental procedure and physical data, see: Yoneda et al (1978). For C-HÁ Á ÁO hydrogen bonds, see: Desiraju & Steiner (1999); Katzsch et al (2011); Fischer et al (2011). For C-HÁ Á ÁS hydrogen bonds, see: Mata et al (2010); Novoa et al (1995); Lu et al (2005); Saad et al (2010).…”

“…The refinement shows the molecules being arranged in a layered structure (Fig. 2) stabilized by C-H•••O (Desiraju et al, 1999;Katzsch et al, 2011;Fischer et al, 2011) and C-H•••S contacts (Mata et al, 2010;Novoa et al, 1995) (Table 1). Two molecules each are associated forming special dimer type species (Fig.…”