Supramolecular hydrogen-bonding patterns in a 1:1 co-crystal of the N(7)—H tautomeric form ofN⁶-benzoyladenine with 4-hydroxybenzoic acid

Abstract

The asymmetric unit of the title co-crystal contains one mol­ecule of N 6-benzoyl­adenine (BA) and one mol­ecule of 4-hy­droxy­benzoic acid (HBA). The N 6-benzoyl­adenine (BA) has an N(7)—H tautomeric form with non-protonated N-1 and N-3 atoms. This tautomeric form is stabilized by a typical intra­molecular N—H⋯O hydrogen bond on the Hoogsteen face of the purine ring. The primary robust (8) ring motif is formed in the Watson–Crick face via N—H⋯O and O—H⋯N hydrogen bonds.

Synthesis, intermolecular interactions and biological activities of two new organic–inorganic hybrids C6H10N2,2Br and C6H10N2,2Cl·H2O

“…Compounds (1) and (2) were prepared by mixing 2-picolylamine (1 mmol; 0.108 g) and 10 mL of distilled water. The resulting solutions were acidied with concentrated hydrobromic acid (1 mmol; 5 drops) for (1) and hydrochloric acid (1 mmol; 5 drops) for (2). The two mixture were stirred magnetically for 10 min at room temperature resulting in the formation of homogeneous solutions.…”

“…Crystal data, data collection and structure renement details for (1) and (2) are summarized in Table 1. Data for crystals (1), were collected on a Bruker D8 VENTURE AXS diffractometer using Mo-Ka radiation.…”

“…Crystal data, data collection and structure renement details for (1) and (2) are summarized in Table 1. Data for crystals (1), were collected on a Bruker D8 VENTURE AXS diffractometer using Mo-Ka radiation. The structure was solved by the dual-space algorithm using the SHELXT program 22 and then rened with full-matrix least-squares methods based on F 2 (SHELXL).…”

“…4(A) and (B), the 2D ngerprint plots from Hirshfeld surface analysis allows quantitative data to be obtained on percentage of element contribution interactions in the molecule. H/Br/Br/H for compound (1) and H/Cl/Cl/H for compound (2) corresponds to 56.3% and 43.8% of the total surface structure provided by the important role of hydrogen bonds in creating strong cohesion between molecules. In addition, the decomposition of ngerprint plots H/H reaction is widespread in the two compounds (1 and 2) and constitutes respectively 33.1% and 36.7% of the total area of Hirshfeld surface.…”

“…In the last twenty years, studies on the self-assembly of molecular salts as well as their hydrogen-bond interactions in the solid-state have evoked a multitude of interest among chemists owing to their intriguing structural diversities and potential applications. 1 Weak intermolecular interactions which are important in the elds of physical, chemical and life sciences represent the backbone of self-assembly processes and supramolecular architectures and exert directional and saturation effects. [2][3][4][5] The hydrogen bond, which is the most common among weak interactions, remains the most important and reliable means of enforcing molecular organization in the solidstate, [6][7][8][9][10][11][12][13] plays a critical role in many chemical and biological processes, and has been a subject of research interest.…”