Likelihood of atom–atom contacts in crystal structures of halogenated organic compounds

Jelsch, Christian; Soudani, Sarra; Nasr, C. Ben

doi:10.1107/s2052252515003255

Cited by 76 publications

(66 citation statements)

References 35 publications

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“…4e6). The enrichment ratios [25] of contacts between the different chemical species were computed in order to highlight which contacts are favored and are likely to be the crystal driving force. Hydrogen atoms bound to carbon (Hc) are distinguished from the polar hydrogen atoms bound to oxygen or nitrogen (Hn/o).…”

Section: Hirshfeld Surface Contacts Analysismentioning

confidence: 99%

Structural, crystal structure, Hirshfeld surface analysis and physicochemical studies of a new chlorocadmate template by 1-(2-hydroxyethyl)piperazine

Soudani

Jeanneau

Jelsch³

et al. 2016

Journal of Molecular Structure

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Section: Hirshfeld Surface Contacts Analysismentioning

confidence: 99%

Structural, crystal structure, Hirshfeld surface analysis and physicochemical studies of a new chlorocadmate template by 1-(2-hydroxyethyl)piperazine

Soudani

Jeanneau

Jelsch³

et al. 2016

Journal of Molecular Structure

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“…[25][26][27][28][29][30][40][41][42] All self contacts between charged atoms (O, N, H N ) are generally avoided as they are not favourable from an electrostatic viewpoint. 95,96 However, in the Cloo and Clmo crystal structures, the N-H and N acceptor atoms are in close proximity resulting in the formation of a double N-H…N hydrogen bond with graph set R 2 2 (8) (around a two-fold axis and inversion centre, respectively) leading to secondary H N …H N contacts. [43][44][45][46] The vast majority of intermolecular interactions are hydrophobic in nature, they constitute the five most represented contacts and four of them have C xy proportions larger than 11%.…”

Section: Contacts Analysismentioning

confidence: 99%

At the Interface of Isomorphous Behavior in a 3 × 3 Isomer Grid of Monochlorobenzamides: Analyses of the Interaction Landscapes via Contact Enrichment Studies

Gallagher

Farrell

Hehir

et al. 2019

Crystal Growth & Design

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The physicochemical properties of a 33 isomer grid of mono-chlorobenzamides (Clxx) are reported with comprehensive studies of their crystal structures and interaction environments (Clx = para-/meta-/ortho-chlorobenzoyl and x = para-/meta-/orthoaminopyridine substitutions). The nine compound Clxx series was synthesised from the three p-/m-/o-chlorobenzoyl chlorides and three p-/m-/o-aminopyridine isomers using standard synthetic procedures. Clxx exhibits some similarities to the related Fxx and Brxx congeners e.g. the isomorphous behaviour of Clpp (para-Chloro-N'-(parapyridyl)benzamide) with several close relatives, and there are five isomorphous pairs of Clxx and Brxx crystal structures. Notably Clmp and Clpm both crystallise with Z'=4 in space group P but show important differences. The overall lack of isomers crystallising with solvate molecules is noteworthy, except for Clmm(H 2 O). In all Clxx crystal structures, strong N-H…N hydrogen bonds form, however, Clpo also crystallises as the unexpected Clpo_O polymorph with N-H…O=C intermolecular hydrogen bonding. The Clxo triad (with orthopyridines) exhibits the expected cyclic N-H…N dimer formation with R 2 2 (8) hydrogen bonded rings. The H C atom type, forming weak C-H…Cl hydrogen bonds, is the only favoured interaction partner of chlorine in Clxx. Conformational analyses (gas phase) together with crystal contact enrichment studies place Clxx in context and at the interface of hydrogen and halogen bonding interactions, though strong hydrogen bonding dominates. In Clxx the interaction energies with nearest neighbours are shown to contribute to most of the lattice electrostatic energies. The melting temperatures T m show correlation with both molecular symmetry (Carnelley's rule) and total electrostatic energy of the weak interactions; in addition, these T m values can be well predicted from a linear fit combining both descriptors. In Clxx, N-H…N hydrogen bonds dominate, largely in the absence of solvates, and with five Clxx forming isomorphous pairs with Brxx analogues; Clpp being isomorphous with several close benzamide relatives. Analysis of T m reveals correlations involving both symmetry and electrostatic energies.

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“…The second group includes organofluorine aromatic compounds where intermolecular interactions between fluorine atoms play a significant role in the stabilization of crystal packing. Moreover, fluorine atoms' interactions can be of many types-weak hydrogen bonds, halogen bonds, F···F interactions, and F···π interactions [68]. Besides, a noticeable contribution to the stabilization of crystal packing is played by other intermolecular interactions with the participation of the π-systems of phenyl rings [69,70].…”

Section: Intermolecular Interactions In the In Situ Crystallized Compmentioning

confidence: 99%

Organoelement Compounds Crystallized In Situ: Weak Intermolecular Interactions and Lattice Energies

2019

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The in situ crystallization is the most suitable way to obtain a crystal of a low-melting-point compound to determine its structure via X-Ray diffraction. Herein, the intermolecular interactions and some crystal properties of low-melting-point organoelement compounds (lattice energies, melting points, etc.) are discussed. The discussed structures were divided into two groups: organoelement compounds of groups 13–16 and organofluorine compounds with other halogen atoms (Cl, Br, I). The most of intermolecular interactions in the first group are represented by weak hydrogen bonds and H···H interactions. The crystal packing of the second group of compounds is stabilized by various interactions between halogen atoms in conjunction with hydrogen bonding and stacking interactions. The data on intermolecular interactions from the analysis of crystal packing allowed us to obtain correlations between lattice energies and Hirshfeld molecular surface areas, molecular volumes, and melting points.

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Likelihood of atom–atom contacts in crystal structures of halogenated organic compounds

Abstract: The analysis, based on Hirshfeld surfaces, reveals which atoms are the preferred partners of halogens in crystal packing contacts.

Cited by 76 publications

References 35 publications

Structural, crystal structure, Hirshfeld surface analysis and physicochemical studies of a new chlorocadmate template by 1-(2-hydroxyethyl)piperazine

Structural, crystal structure, Hirshfeld surface analysis and physicochemical studies of a new chlorocadmate template by 1-(2-hydroxyethyl)piperazine

At the Interface of Isomorphous Behavior in a 3 × 3 Isomer Grid of Monochlorobenzamides: Analyses of the Interaction Landscapes via Contact Enrichment Studies

Organoelement Compounds Crystallized In Situ: Weak Intermolecular Interactions and Lattice Energies

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