Crystal structure and Hirshfeld analysis of the kryptoracemate: bis(mefloquinium) chloride p-fluorobenzenesulphonate

Jotani, Mukesh M.; Wardell, James L.; Tiekink, Edward R. T.

doi:10.1515/zkri-2015-1914

Cited by 15 publications

(12 citation statements)

References 32 publications

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“…The Hirshfeld surface calculations were carried out for the polymorphs 1 and 2 in accord with a recent study on an organic salt [39]. The results provide additional insight into the influence of non-covalent interactions on their molecular packing and assist in differentiating between the independent species found in 1 and 2.…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

Supramolecular association in the triclinic (Z′=1) and monoclinic (Z′=4) polymorphs of 4-(4-acetylphenyl)piperazin-1-ium 2-amino-4-nitrobenzoate

Jotani¹,

Wardell

Tiekink

2018

Zeitschrift Für Kristallographie - Crystalline Materials

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Crystallography reveals two polymorphs for the salt [4-(4-acetylphenyl)piperazin-1-ium][2-amino-4-nitrobenzoate], a monoclinic form (2; modelled as P21/n with Z′=4) formed directly from the reaction mixture, and a triclinic form (1; Z′=1) isolated from recrystallisation. Relatively minor differences are noted in the conformations of the anions and of the cations, mainly relating to the twist of, respectively, the carboxylate groups and piperazin-1-ium rings with respect to the phenyl rings they are connected to. The key feature of the packing of both forms is the formation of charge-assisted ammonium-N–H···O (carboxylate) hydrogen bonds which lead to cyclic 12-membered {···HNH ···OCO}2 synthons in the case of 1 but, supramolecular chains in 2. The three-dimensional architecture in the crystal of 1 is further stabilised by amine-N–H···O (nitro) and amine-N–H···O (acetyl) hydrogen bonds, leading to double-layers in the bc-plane, which are linked along the a-axis by methylene-C–H···O (carboxylate) and π-stacking interactions. The combination of ammonium-N–H···O (carboxylate) and amine-N–H···O (carboxylate, acetyl) hydrogen bonds consolidate the three-dimensional packing in the crystal of 2. The greater crystal density, packing efficiency and calculated lattice energy for 1 compared with 2, suggest the former to be the thermodynamically most stable crystal. An analysis of the Hirshfeld surfaces for 1 and 2 reveal distinctive features that differentiate between the constituents of the two forms and between the ions comprising the asymmetric unit of 2.

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Section: Hirshfeld Surface Analysismentioning

confidence: 99%

Supramolecular association in the triclinic (Z′=1) and monoclinic (Z′=4) polymorphs of 4-(4-acetylphenyl)piperazin-1-ium 2-amino-4-nitrobenzoate

Jotani¹,

Wardell

Tiekink

2018

Zeitschrift Für Kristallographie - Crystalline Materials

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“…A review of this phenomenon has appeared for organic compounds (Fá biá n & Brock, 2010) where such behaviour is found in only 0.1% of structures. There are about 30 mefloquine/derivatives in the Cambridge Structural Database (Groom et al, 2016) and of these, there are two examples of kryptoracemates (Jotani et al, 2016;Wardell, Wardell et al, 2016). Further, in a very recent study, 34 new mefloquine salts were reported of which two were kryptoracemates (Engwerda et al, 2019).…”

Section: Database Surveymentioning

confidence: 99%

Bis(mefloquinium) butanedioate ethanol monosolvate: crystal structure and Hirshfeld surface analysis

Wardell

Jotani²,

Tiekink

2019

Acta Cryst E

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The asymmetric unit of the centrosymmetric title salt solvate, 2C17H17F6N2O+· C4H4O4 2−·CH3CH2OH, (systematic name: 2-{[2,8-bis(trifluoromethyl)quinolin-4-yl](hydroxy)methyl}piperidin-1-ium butanedioate ethanol monosolvate) comprises two independent cations, with almost superimposable conformations and each approximating the shape of the letter L, a butanedioate dianion with an all-trans conformation and an ethanol solvent molecule. In the crystal, supramolecular chains along the a-axis direction are sustained by charge-assisted hydroxy-O—H...O(carboxylate) and ammonium-N—H...O(carboxylate) hydrogen bonds. These are connected into a layer via C—F...π(pyridyl) contacts and π–π stacking interactions between quinolinyl-C6 and –NC5 rings of the independent cations of the asymmetric unit [inter-centroid separations = 3.6784 (17) and 3.6866 (17) Å]. Layers stack along the c-axis direction with no directional interactions between them. The analysis of the calculated Hirshfeld surface reveals the significance of the fluorine atoms in surface contacts. Thus, by far the greatest contribution to the surface contacts, i.e. 41.2%, are of the type F...H/H...F and many of these occur in the inter-layer region. However, these contacts occur at separations beyond the sum of the van der Waals radii for these atoms. It is noted that H...H contacts contribute 29.8% to the overall surface, with smaller contributions from O...H/H...O (14.0%) and F...F (5.7%) contacts.

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“…The Hirshfeld surfaces calculated for (I) were performed in accord with recent studies (Jotani et al, 2016) Intra-and intermolecular interactions (Å , ) for (I).…”

Section: Hirshfeld Surface Analysismentioning

confidence: 99%

N-(6-Methoxypyridin-2-yl)-1-(pyridin-2-ylmethyl)-1H-pyrazole-3-carboxamide: crystal structure and Hirshfeld surface analysis

Ramani

Shah

Jotani³

et al. 2018

Acta Cryst E

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Crystal structure and Hirshfeld analysis of the kryptoracemate: bis(mefloquinium) chloride p-fluorobenzenesulphonate

Cited by 15 publications

References 32 publications

Supramolecular association in the triclinic (Z′=1) and monoclinic (Z′=4) polymorphs of 4-(4-acetylphenyl)piperazin-1-ium 2-amino-4-nitrobenzoate

Supramolecular association in the triclinic (Z′=1) and monoclinic (Z′=4) polymorphs of 4-(4-acetylphenyl)piperazin-1-ium 2-amino-4-nitrobenzoate

Bis(mefloquinium) butanedioate ethanol monosolvate: crystal structure and Hirshfeld surface analysis

N-(6-Methoxypyridin-2-yl)-1-(pyridin-2-ylmethyl)-1H-pyrazole-3-carboxamide: crystal structure and Hirshfeld surface analysis

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