Abstract
Hexa-methyl-ene-tetra-mine carboacetamino-phenborane, a mol-ecule with two pharmacophores attached to a central carb-oxy-borate moiety, was synthesized and crystals were grown with an acetamino-phen co-crystal former to result in the title 1:1 co-crystal [hexa-methyl-ene-tetra-mine 4-acetamido-phenyl 2-boranyl-acetate-4-acet-amido-phenol (1/1)], C15H22BN5O3·C8H9NO2. In the first of these mol-ecules, both the borate-ester and acetyl-amino groups are considerably twisted away from the plane of the inter-vening benzene ring [dihedral angles = 76.89 (9) and 65.42 (9)°, respectively]. The extended structure of this co-crystal features N-H⋯O and O-H⋯O hydrogen bonds, which link the components into (100) sheets and weak C-H⋯O hydrogen bonds help to consolidate the structure.
Highlights
Hexamethylenetetramine carboacetaminophenborane, a molecule with two pharmacophores attached to a central carboxyborate moiety, was synthesized and crystals were grown with an acetaminophen co-crystal former to result in the title 1:1 co-crystal [hexamethylenetetramine 4-acetamidophenyl 2-boranylacetate–4-acetamidophenol (1/1)], C15H22BN5O3ÁC8H9NO2
Our interest in amine carboxyboranes stemmed from their innate structure that undergoes decarbonylation to produce CO, H2, and the amine group when placed in aqueous solution
As part of this work, we describe the crystal structure of the title co-crystal, C15H22BN5O3ÁC8H9NO2, (I), which resulted from the synthetic concept that conjugating two different pharmacophores to the carboxyborate moiety may make a molecule that has multiple biological effects
Summary
Crystal structures of pure drugs are of great interest in the pharmaceutical industry since these structures provide an understanding of the intermolecular interactions that explain the physical and chemical properties of the solid (Desiraju, 2007). A group of organo–boron compounds, namely amine carboxyboranes, have been studied extensively for their diverse biological effects such as anti-inflammatory, antineoplastic and anti-osteoporotic activities (Hall et al, 1995, 1990; Murphy et al, 1996). Their fundamental structure contains tetravalent amines connected to a boron atom of the carboxyborane moiety with an N—B coordinate covalent bond (Spielvogel et al, 1976). The only significant difference is in the slightly longer C9—O2 single bond, 1.399 (2) Ain the difunctionalized title compound compared to 1.353 (3) Ain CORCB-1. In the co-crystallized acetaminophen molecule in (I), the dihedral angle between the C18–C23 benzene ring and the acetylamino C16/C17/N6/O5 grouping is 54.61 (10)
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