scholarly journals Interplay of Hydrogen and Halogen Bonding in the Crystal Structures of 2,6‐Dihalogenated Phenols

2021 ◽  
Vol 6 (33) ◽  
pp. 8736-8740
Author(s):  
Jonathan O. Bauer ◽  
Sarah Koschabek ◽  
Alexander Falk
Keyword(s):  
Crystal Structures ◽  
Halogen Bonding

Halogen-bonding in a new family of tris(haloanilato)metallate(iii) magnetic molecular building blocks

2014 ◽  
Vol 43 (19) ◽  
pp. 7006-7019 ◽  
Author(s):  
Matteo Atzori ◽  
Flavia Artizzu ◽  
Elisa Sessini ◽  
Luciano Marchiò ◽  
Danilo Loche ◽  
...  
Keyword(s):  
Magnetic Properties ◽  
Dft Calculations ◽  
Crystal Structures ◽  
General Formula ◽  
Halogen Bonding ◽  
Building Blocks ◽  
New Family ◽  
Molecular Building Blocks

Here we report on new tris(haloanilato)metallate(iii) complexes with general formula [M(X2An)3]3−, their crystal structures, DFT calculations and magnetic properties.

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

IUCrJ ◽  
2015 ◽  
Vol 2 (3) ◽  
pp. 327-340 ◽  
Author(s):  
Christian Jelsch ◽  
Sarra Soudani ◽  
Cherif Ben Nasr
Keyword(s):  
Chemical Composition ◽  
Crystal Structures ◽  
Organic Compounds ◽  
Chemical Species ◽  
Halogen Bonding ◽  
Molecular Surface ◽  
Analysis Tool ◽  
Halogenated Organic Compounds ◽  
High Propensity ◽  
Crystal Contacts

The likelihood of occurrence of intermolecular contacts in crystals of halogenated organic compounds has been analysed statistically using tools based on the Hirshfeld surface. Several families of small halogenated molecules (containing organic F, Cl, Br or I atoms) were analysed, based on chemical composition and aromatic or aliphatic character. The behaviour of crystal contacts was also probed for molecules containing O or N. So-called halogen bonding (a halogen making short interactions with O or N, or a π interaction with C) is generally disfavoured, except when H is scarce on the molecular surface. Similarly, halogen...halogen contacts are more rare than expected, except for molecules that are poor in H. In general, the H atom is found to be the preferred partner of organic halogen atoms in crystal structures. On the other hand, C...C interactions in parallel π-stacking have a high propensity to occur in halogenated aromatic molecules. The behaviour of the four different halogen species (F, Cl, Br, I) is compared in several chemical composition contexts. The analysis tool can be refined by distinguishing several types for a given chemical species, such as H atoms bound to O or C. Such distinction shows, for instance, that C—H...Cl and O—H...O are the preferred interactions in compounds containing both O and Cl.

4,5-Dihaloimidazolium-based ionic liquids: effects of halogen-bonding on crystal structures and ionic conductivity

RSC Advances ◽  
2013 ◽  
Vol 3 (43) ◽  
pp. 19952 ◽  
Author(s):  
Tomohiro Mukai ◽  
Keiko Nishikawa
Keyword(s):  
Ionic Liquids ◽  
Ionic Conductivity ◽  
Crystal Structures ◽  
Halogen Bonding

Crystal structures of four δ-keto esters and a Cambridge Structural Database analysis of cyano–halogen interactions

2015 ◽  
Vol 71 (10) ◽  
pp. 921-928 ◽  
Author(s):  
Kulsoom Kamal ◽  
Hardesh K. Maurya ◽  
Atul Gupta ◽  
Prema G. Vasudev
Keyword(s):  
Crystal Structures ◽  
Crystal Packing ◽  
Noncovalent Interactions ◽  
Halogen Bonding ◽  
Cambridge Structural Database ◽  
Database Analysis ◽  
Molecular Conformations ◽  
Keto Esters ◽  
Organic Molecular Crystals ◽  
Structural Database

The revived interest in halogen bonding as a tool in pharmaceutical cocrystals and drug design has indicated that cyano–halogen interactions could play an important role. The crystal structures of four closely related δ-keto esters, which differ only in the substitution at a single C atom (by H, OMe, Cl and Br), are compared, namely ethyl 2-cyano-5-oxo-5-phenyl-3-(piperidin-1-yl)pent-2-enoate, C19H22N2O3, (1), ethyl 2-cyano-5-(4-methoxyphenyl)-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C20H24N2O4, (2), ethyl 5-(4-chlorophenyl)-2-cyano-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C19H21ClN2O3, (3), and the previously published ethyl 5-(4-bromophenyl)-2-cyano-5-oxo-3-(piperidin-1-yl)pent-2-enoate, C19H21BrN2O3, (4) [Maurya, Vasudev & Gupta (2013).RSC Adv.3, 12955–12962]. The molecular conformations are very similar, while there are differences in the molecular assemblies. Intermolecular C—H...O hydrogen bonds are found to be the primary interactions in the crystal packing and are present in all four structures. The halogenated derivatives have additional aromatic–aromatic interactions and cyano–halogen interactions, further stabilizing the molecular packing. A database analysis of cyano–halogen interactions using the Cambridge Structural Database [CSD; Groom & Allen (2014).Angew. Chem. Int. Ed.53, 662–671] revealed that about 13% of the organic molecular crystals containing both cyano and halogen groups have cyano–halogen interactions in their packing. Three geometric parameters for the C—X...N[triple-bond]C interaction (X = F, Cl, Br or I),viz.the N...Xdistance and the C—X...N and C—N...Xangles, were analysed. The results indicate that all the short cyano–halogen contacts in the CSD can be classified as halogen bonds, which are directional noncovalent interactions.

scholarly journals The Role of Halogen Bonding in Crystal Structures of 3-Halogeno Cytisine Derivatives

2012 ◽  
Vol 42 (7) ◽  
pp. 685-690 ◽  
Author(s):  
Anna K. Przybył ◽  
Maciej Kubicki
Keyword(s):  
Crystal Structures ◽  
Halogen Bonding ◽  
Cytisine Derivatives

[2+2] Halogen-bonded boxes employing azobenzenes

2019 ◽  
Vol 55 (60) ◽  
pp. 8768-8771 ◽  
Author(s):  
Esther Nieland ◽  
Thomas Topornicki ◽  
Tom Kunde ◽  
Bernd M. Schmidt
Keyword(s):  
Crystal Structures ◽  
Halogen Bonding

Herein, we report the synthesis and crystal structures of three [2+2] supramolecular boxes assembled by halogen bonding.

The role of weak hydrogen and halogen bonding interactions in the assembly of a series of Hg(ii) coordination polymers

2015 ◽  
Vol 44 (12) ◽  
pp. 5703-5712 ◽  
Author(s):  
Alireza Azhdari Tehrani ◽  
Ali Morsali ◽  
Maciej Kubicki
Keyword(s):  
Crystal Structures ◽  
Coordination Polymers ◽  
Halogen Bonding ◽  
Theoretical Methods

A series of eight new Hg(ii) complexes based on the L4-X ligands, where L is (E)-4-halo-N-(pyridin-4-ylmethylene)aniline, were synthesized and characterized and their supramolecular crystal structures were studied by different geometrical and theoretical methods.

Utilizing plane group symmetry to favor noncentrosymmetry in three-dimensional crystals

2020 ◽  
Vol 98 (7) ◽  
pp. 327-331
Author(s):  
Ren A. Wiscons ◽  
Adam J. Matzger
Keyword(s):  
Crystal Structures ◽  
Second Harmonic ◽  
Three Dimensional ◽  
Halogen Bonding ◽  
Two Dimensions ◽  
Group Symmetry ◽  
Inversion Symmetry ◽  
Closest Packing ◽  
Symmetry Operators ◽  
Plane Group

Materials that lack inversion symmetry (noncentrosymmetric) demonstrate a diversity of desirable optical and electronic properties in bulk such as second harmonic generation, chiral emission, and piezo-, pyro-, and ferro-electricity. Unfortunately, it is challenging to reliably access noncentrosymmetric packing motifs because the closest packing of molecules is often achieved through inversion symmetry operators, leading to the relatively low occurrence of noncentrosymmetry in organic crystals. In this study, the occurrence of noncentrosymmetry in materials that adopt planar packing motifs is investigated because molecular species achieve closest packing in two dimensions through rotations and (or) glides, symmetry operators that do not individually lead to centrosymmetry. It is found that of the 18 crystal structures investigated here adopting planar packing motifs, 13 structures (72%) are noncentrosymmetric showing in-plane polarization. The 13 noncentrosymmetric crystal structures differ from the centrosymmetric structures by directional halogen bonding interactions or steric collisions that align the polarization directions of neighboring layers, leading to bulk structural polarity. The results from this investigation will be of use for designing noncentrosymmetric materials for application in optical and electronic devices.

Probing the O⋯Br–Br halogen bonding in X-ray crystal structures with ab initio calculations

CrystEngComm ◽  
2012 ◽  
Vol 14 (5) ◽  
pp. 1833 ◽  
Author(s):  
Rabindranath Lo ◽  
Amar Ballabh ◽  
Ajeet Singh ◽  
Parthasarathi Dastidar ◽  
Bishwajit Ganguly
Keyword(s):  
Ab Initio Calculations ◽  
Ab Initio ◽  
Crystal Structures ◽  
Halogen Bonding ◽  
X Ray

Crystal Structures and Spin crossover of Iron(III) Cocrystal Formed via Halogen Bonding

2021 ◽  
Author(s):  
Hikaru Zenno ◽  
Ryohei Akiyoshi ◽  
Masaaki Nakamura ◽  
Yoshitiro Sekine ◽  
Shinya Hayami
Keyword(s):  
Crystal Structures ◽  
Spin Crossover ◽  
Halogen Bonding
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