<i>N</i>′-(4-Hydroxybenzylidene)isonicotinohydrazide

Deng, Qiling; Yu, Miao; Chen, Xin; Diao, Chun-Hua; Jing, Zuo‐Liang; Fan, Zhi

doi:10.1107/s1600536805022191

Cited by 8 publications

(7 citation statements)

References 3 publications

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“…Here, the structural features of the hydroxyl analogue of IsI and IsBr are investigated. So far, two X-ray structures of N 0 -(4-hydroxybenzylidene)isonicotinohydrazide have been reported, namely in pure form (IsOH) and as the monohydrate (IsOHÁH 2 O) (Deng et al, 2005;Tai et al, 2007). In IsOH, molecules are superposed in a parallel displaced stacking and head-to-tail mode, with rather short OÁ Á ÁCe (pyridyl ring centre) and NÁ Á ÁCe (phenyl ring centre) distances of 3.298 and 3.449 Å , respectively (Fig.…”

Section: Structural Features Of Isoniazid-based Hydrazonesmentioning

confidence: 99%

Crystal packing and theoretical analysis of halogen- and hydrogen-bonded hydrazones from pharmaceuticals. Evidence of type I and II halogen bonds in extended chains of dichloromethane

Berger

Soubhye

Wintjens

et al. 2018

Acta Crystallogr Sect B

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The supramolecular assembly of halogenated and hydroxyl hydrazones derived from two well known pharmaceuticals, isoniazid (IsX, where X = I, Br, OH) and hydralazine (HyX, where X = I, Br, OH), was studied by X-ray crystallography and theoretical methods. Crystal packing of IsI and HyI shows weak IÁ Á ÁN and IÁ Á Á halogen bonds, whereas the hydrogen bonds are dominant in the brominated scaffolds IsBr and HyBr. Although the calculated IÁ Á ÁN interaction strength appears almost three times weaker than the O-HÁ Á ÁN contacts in the isoniazid-based hydrazones, the higher directionality of the halogen bonds induces a linear and planar architecture of self-complementary tectons, observed only with the help of a bridging water molecule in the case of IsOH. Finally, the X-ray structure of HyOH is characterized by an unexpected linear arrangement of clathrated dichloromethane molecules bound through type I and II halogen bonds. This rare phenomenon, observed in less than ten structures, was studied by coupled cluster-based energy decomposition.

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Section: Structural Features Of Isoniazid-based Hydrazonesmentioning

confidence: 99%

Crystal packing and theoretical analysis of halogen- and hydrogen-bonded hydrazones from pharmaceuticals. Evidence of type I and II halogen bonds in extended chains of dichloromethane

Berger

Soubhye

Wintjens

et al. 2018

Acta Crystallogr Sect B

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“…Crystallization of HBIH molecules led to the formation of three different solid forms, which were governed by the employed conditions. Single crystals of PA were obtained by slow evaporation of the solution of p-hydroxybenzaldehyde isonicotinic acid hydrazone in methanol at 293 K. Forms PB and PC were reprepared by adopting different synthetic routes than their previously reported structures and therefore their crystal structures were redetermined by single-crystal X-ray diffraction to compare with the originally published structures [18,19]. All the crystallographic parameters are similar for the structures PB and PC.…”

Section: Comments On Synthesismentioning

confidence: 99%

Solid State Analysis and Theoretical Explorations on Polymorphic and Hydrate Forms of p-Hydroxybenzaldehyde Isonicotinichydrazone: Effect of Additives on Polymorphic Crystallization

Va²,

Jp³

et al. 2018

Preprint

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The reaction of p-hydroxybenzaldehyde with an equimolar amount of isonicotinic hydrazide afforded two polymorphic and hydrate forms of p-hydroxybenzaldehyde isonicotinichydrazone (HBIH) by varying the experimental reaction conditions. The compounds are fully characterized by means of single crystal and powder diffraction methods, vibrational spectroscopy (FT-IR and Raman), thermal and elemental analysis. The compound crystallizes in three different forms in two different space groups, P21/c (form PA and PB) and Pbca (PC). The Hirshfeld surface analysis shows the differences in the relative contributions of intermolecular interactions to the total Hirshfeld surface area for the HBIH molecules. The calculated pairwise interaction energies (104-116 kJ/mol) can be related to the stability of the crystals. Energy framework analysis identifies the interaction hierarchy and their topology. The geometry and conformation of the three forms are essentially similar which differ only by packing arrangement.

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“…For general background to metal complexes with Shiff bases, see: Kahwa et al (1986); Deng et al (2005). For related structures, see: Guo et al (2006); Jing et al (2005); Santos et al (2001); Yu et al (2005).…”

Section: Related Literaturementioning

confidence: 99%