Atom interaction propensities of oxygenated chemical functions in crystal packings

Jelsch, Christian; Bisseyou, Yvon Bibila Mayaya

doi:10.1107/s2052252516020200

Cited by 24 publications

(25 citation statements)

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“…R-factor definitions as R[F 2 > 2(F 2 )], wR(F 2 ). 51 Methods [58][59][60][61][62] Electrostatic energy calculations were performed with the MoProSuite software. 58 The multipolar electron density of the molecules was modelled by transfer of the ELMAM2 charge density database without further refinement.…”

Section: Materials Methods and Equipmentmentioning

confidence: 99%

“…61 The polar H N and hydrophobic H C atoms were distinguished. Crystal contact enrichment ratios were averaged, as noted by Jelsch and Bisseyou: 62 arithmetically and harmonically, for values smaller and larger than unity, respectively. 62 Supplementary Figures and Tables are provided (ESI; Figures S4-S10; Tables S4-S7).…”

Section: Materials Methods and Equipmentmentioning

confidence: 99%

“…Crystal contact enrichment ratios were averaged, as noted by Jelsch and Bisseyou: 62 arithmetically and harmonically, for values smaller and larger than unity, respectively. 62 Supplementary Figures and Tables are provided (ESI; Figures S4-S10; Tables S4-S7). Dimers Footnotes: C 6 is the (C11,...,C16) benzene ring and C 5 N is the (C21,...,C26) pyridine ring defined for the least squares (LS) planes in Scheme 2; the bridging amide plane is defined as the 5 atom C ipso -C(O)NC ipso (or C11, C1, O1, N1, C21) LS plane, with reference to…”

Section: Materials Methods and Equipmentmentioning

confidence: 99%

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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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Section: Materials Methods and Equipmentmentioning

confidence: 99%

Section: Materials Methods and Equipmentmentioning

confidence: 99%

Section: Materials Methods and Equipmentmentioning

confidence: 99%

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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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“…Hydrogen bonding plays an important role in the crystallization of molecules (Minkov et al, 2015;Zick & Geiger, 2018;Swinton Darious et al, 2018;Bekö et al, 2014) and has a strong influence on phase transitions (Fortes et al, 2014;Binns et al, 2016). It is worth noting that not only strong N-HÁ Á ÁO and O-HÁ Á ÁO hydrogen bonds, but also weak C-HÁ Á ÁO hydrogen bonds, are important in the formation of structural networks in crystals (Jelsch & Bibila Mayaya Bisseyou, 2017). As early as 1982, Taylor & Kennard (1982) provided evidence for the presence of dominant C-HÁ Á ÁO interactions in crystals.…”

Section: Introductionmentioning

confidence: 98%

Three new quinuclidine-based structures: second harmonic generation response for 1,2-bis(1-azoniabicyclo[2.2.2]octan-3-ylidene)hydrazine dichloride

et al. 2019

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The crystal structures of three quinuclidine‐based compounds, namely (1‐azabicyclo[2.2.2]octan‐3‐ylidene)hydrazine monohydrate, C7H13N3·H2O (1), 1,2‐bis(1‐azabicyclo[2.2.2]octan‐3‐ylidene)hydrazine, C14H22N4 (2), and 1,2‐bis(1‐azoniabicyclo[2.2.2]octan‐3‐ylidene)hydrazine dichloride, C14H24N42+·2Cl− (3), are reported. In the crystal structure of 1, the quinuclidine‐substituted hydrazine and water molecules are linked through N—H…O and O—H…N hydrogen bonds, forming a two‐dimensional array. The compound crystallizes in the centrosymmetric space group P21/c. Compound 2 was refined in the space group Pccn and exhibits no hydrogen bonding. However, its hydrochloride form 3 crystallizes in the noncentrosymmetric space group Pc. It shows a three‐dimensional network structure via intermolecular hydrogen bonding (N—H…C and N/C—H…Cl). Compound 3, with its acentric structure, shows strong second harmonic activity.

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“…Nowadays, information about the crystal structures of discrete organic and organometallic compounds allows us to reformulate principles of their packing [23,24], and to investigate intermolecular interactions more thoroughly. Not only information about geometry and frequency of occurrence of an unusual interaction, synthon, or tecton is extracted from the CSD to support a conclusion about its' role in crystal packing and electronic effects that cause its' appearance [25][26][27][28][29]; but it is also recommended to additionally compare interaction occurrence relative to what would be expected at random [30][31][32][33]. Crystals 2019, 9, 478 3 of 40Data about molecular geometry-from bond lengths and angles to torsions and ring geometry-form the basis of our understanding of the energetics of molecular conformation.…”

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confidence: 99%

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

Вологжанина

2019

Crystals

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Intermolecular interactions of organic, inorganic, and organometallic compounds are the key to many composition-structure and structure-property networks. In this review, some of these relations and the tools developed by the Cambridge Crystallographic Data Center (CCDC) to analyze them and design solid forms with desired properties are described. The potential of studies supported by the Cambridge Structural Database (CSD)-Materials tools for investigation of dynamic processes in crystals, for analysis of biologically active, high energy, optical, (electro)conductive, and other functional crystalline materials, and for the prediction of novel solid forms (polymorphs, co-crystals, solvates) are discussed. Besides, some unusual applications, the potential for further development and limitations of the CCDC software are reported. Crystals 2019, 9, 478 2 of 40 these fields, the manuscript cites only (i) recent works devoted to the analysis of correlations between intermolecular interactions and properties of a small molecule (for example its inclination to form polymorphs, solvates, and co-crystals), or a corresponding solid (from a well-known requirement for non-linear optical materials to crystallize in acentric space groups, to recent studies devoted to the effect of solvent presence on mechanical properties), and (ii) the corresponding software developed to investigate these correlations and to design novel solid forms with desired physicochemical properties. As the description of structure-property networks describes mainly the papers published in the last 10 years in the field of organic, organometallic, and coordination crystals, then the software under discussion will be limited with those developed by the Cambridge Crystallographic Data Centre (CCDC) for material chemistry and crystallography. Various examples of applications of the CCDC software to functional materials including their combination with other software, and restrictions found, will be given.First, the Cambridge Structural Database (CSD) and components of the CSD-Enterprise will be described in Section 2. Then, some properties related to the appearance of a given supramolecular associate, and the tools to search for an associate in the CSD will be reported in Section 3. The properties of solids dependent on the crystal morphology, the Bravais, Friedel, Donnay, and Harker (BFDH) tool for crystal morphology prediction and its' application to affect crystal morphology, polymorphism, and solvatomorphism will be reported in Section 4. Knowledge-based predictions of H-bonded polymorphism, co-crystal formation, mapping of likely intermolecular interactions, and conformer generation for the synthesis of novel functional materials will be discussed in Section 5, and the analysis of local connectivity and whole architectures of solvent molecules in Section 6. Finally, Section 7 contains information about Python API algorithms compatible with the CSD-Enterprise and about some examples of the successful combination of the CSD-Enterprise tools with exte...

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Atom interaction propensities of oxygenated chemical functions in crystal packings

Abstract: Intermolecular crystal contacts formed by different oxygen atom types are investigated.

Cited by 24 publications

References 60 publications

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

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

Three new quinuclidine-based structures: second harmonic generation response for 1,2-bis(1-azoniabicyclo[2.2.2]octan-3-ylidene)hydrazine dichloride

Intermolecular Interactions in Functional Crystalline Materials: From Data to Knowledge

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