A discussion on the solid state organization of 4-pyridyl imino compounds and on the co-crystallization between their molecular precursors

Abstract

The synthesis and the crystal structures of several 4-pyridyl imino compounds are reported. Their solidstate organization is based on head-to-tail chains sustained by O-H/N hydrogen bonds; the supramolecular arrangement is analysed by means of the Hirshfeld surfaces and of the corresponding 2D-fingerprint plots. The co-crystallization between 4-aminobenzyl alcohol and 4-acetylpyridine is analysed, correlating reactivity trends and structural characters. In this context, the single crystal X-ray diffraction analyses of 4-aminobenzyl alcohol and 3,5-diphenyl-4-hydroxyaniline are also reported.

The X-ray Structure of 4-Aminobenzyl alcohol (4-Aminophenylmethanol)

“…The hydrogen-bonding pattern is remarkably different from those involved for the previously reported structure of 1 [6], and the other isomers 2 and 3. We attribute the isolation of a second form of 1 to recrystallization of our sample 1 3…”

“…In addition, hydrogen-bonding patterns in structures of the closely related ortho-, meta-and para-hydroxybenzyl alcohols 4-6 have been examined in detail [4,5] (Scheme 1). We determined the X-ray structure and, at that stage, found a previously published structure [6] but the two were markedly different. In this paper, we describe the crystal and molecular structure of the new polymorph of 1 and compare the observed hydrogen-bonding patterns with those for the originally reported polymorph and related compounds.…”

“…Schematic hydrogen bonding pattern in the crystal structure of Geometric parameters for intermolecular hydrogen bonding in 1 Hydrogen bonding pattern in the previously reported polymorph of 1 viewed along the c axis[6] …”

Solid-state supramolecular architectures of a series of Hg(ii) halide coordination compounds based on hydroxyl-substituted Schiff base ligands

“…The Schiff base ligands, 2-((pyridin-3ylmethylene)amino)phenol (L1) and 4-((pyridin-4-ylmethylene)amino)phenol (L2), were prepared according to the previously reported method. 28 The infrared spectra were recorded on a Nicolet Fourier Transform IR, Nicolet 100 spectrometer in the range 500-4000 cm -1 using the KBr disk technique. Elemental analyses (carbon, hydrogen and nitrogen) were performed using an ECS 4010 CHN-O made in Costech, Italy.…”

Cocrystal Systems of Pharmaceutical Interest: 2009

“…Structures of the cocrystal products, and identification of 3 supramolecular synthons useful for the prediction of structural motifs [61] Glutaric acid Urea Discovery of a new 1:1 cocrystal by construction of the ternary phase diagram [62] Fumaric acid Nicotinamide Characterization of the amide-acid heterosynthon in the 1:1 cocrystal and the amide-amide homosynthon in the 2:1 cocrystal [63] Cyanooxime compounds N-heterocycle compounds Study of the versatility of cyanooximes as hydrogen-bond donors when interacted with asymmetric ditopic N-heterocyclics 4-Aminobenzyl alcohol 4-Acetylpyridine Structural analysis of the 1:1 cocrystal, as well as the structures of several related compounds [69] 4-p-Hydroxyphenyl-2,2,4-trimethyl-chroman…”