Halogen Bond as Controlling the Crystal Structure of 4-Amino-3,5-Dihalogenobenzoic Acid and Its Effect on the Positional Ordering/Disordering of Acid Protons

2014 ◽  
Vol 14 (12) ◽  
pp. 6189-6196 ◽  
Author(s):  
Kouhei Ueda ◽  
Masaharu Oguni ◽  
Tetsuo Asaji
Keyword(s):  
Crystal Structure ◽  
Halogen Bond

scholarly journals Cocrystal Assembled by Pyrene Derivative and 1,4-Diiodotetrafluorobenzene via a C=O···I Halogen Bond

Crystals ◽  
2018 ◽  
Vol 8 (10) ◽  
pp. 392 ◽  
Author(s):  
Qi Feng ◽  
Wenhui Huan ◽  
Jiali Wang ◽  
Fang Guo ◽  
Jiadan Lu ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Halogen Bond ◽  
Hirshfeld Surface ◽  
Vibration Band ◽  
Characteristic Vibration ◽  
Face To Face ◽  
The Face ◽  
Ft Ir ◽  
Conjugated Compounds ◽  
Ft Ir Spectroscopy

Cocrystal formation is a strategy used to modify the solid-state properties of a given molecule. In this study, a new cocrystal assembled by 1,4-Diiodotetrafluorobenzene (1,4-DITFB) and a pyrene derivative, 1-acetyl-3-phenyl-5-(1-pyrenyl)-pyrazoline (APPP), was synthesized. Due to the twisted structure of APPP, the crystal structure is greatly different with some large π-conjugated compounds, which exhibits edge-to-face π-stacked arrangement between 1,4-DITFB and pyrene rings, rather than the face-to-face π-stacked arrangement. Hirshfeld surface analysis and the shift of characteristic vibration band of the carbonyl group in FT-IR spectroscopy suggest the formation of a C=O···I halogen bond.

scholarly journals Noncovalent Interactions between 1,3,5-Trifluoro-2,4,6-triiodobenzene and a Series of 1,10-Phenanthroline Derivatives: A Combined Theoretical and Experimental Study

Crystals ◽  
2019 ◽  
Vol 9 (3) ◽  
pp. 140 ◽  
Author(s):  
Yu Zhang ◽  
Jian-Ge Wang ◽  
Weizhou Wang
Keyword(s):  
Crystal Structure ◽  
Crystal Structures ◽  
Quantum Chemical ◽  
Halogen Bond ◽  
Noncovalent Interactions ◽  
Stacking Interactions ◽  
Halogen Bonds ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Structural Competition

How many strong C−I⋯N halogen bonds can one 1,3,5-trifluoro-2,4,6-triiodobenzene molecule form in a crystal structure? To answer this question, we investigated in detail the noncovalent interactions between 1,3,5-trifluoro-2,4,6-triiodobenzene and a series of 1,10-phenanthroline derivatives by employing a combined theoretical and experimental method. The results of the quantum chemical calculations and crystallographic experiments clearly show that there is a structural competition between a C−I⋯N halogen bond and π⋯π stacking interaction. For example, when there are much stronger π⋯π stacking interactions between two 1,10-phenanthroline derivative molecules or between two 1,3,5-trifluoro-2,4,6-triiodobenzene molecules in the crystal structures, then one 1,3,5-trifluoro-2,4,6-triiodobenzene molecule forms only one C−I⋯N halogen bond with one 1,10-phenanthroline derivative molecule. Another example is when π⋯π stacking interactions in the crystal structures are not much stronger, one 1,3,5-trifluoro-2,4,6-triiodobenzene molecule can form two C−I⋯N halogen bonds with two 1,10-phenanthroline derivative molecules.

Crystal structure and photoreactivity of a halogen-bonded cocrystal based upon 1,2-diiodoperchlorobenzene and 1,2-bis(pyridin-4-yl)ethylene

2020 ◽  
Vol 76 (6) ◽  
pp. 557-561
Author(s):  
Eric Bosch ◽  
Jessica D. Battle ◽  
Ryan H. Groeneman
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Ultraviolet Light ◽  
Halogen Bond ◽  
Cycloaddition Reaction ◽  
Solvent Free ◽  
Halogen Bonds ◽  
Face To Face ◽  
Similar Yield

The formation of a photoreactive cocrystal based upon 1,2-diiodoperchlorobenzene (1,2-C6I2Cl4 ) and trans-1,2-bis(pyridin-4-yl)ethylene (BPE) has been achieved. The resulting cocrystal, 2(1,2-C6I2Cl4 )·(BPE) or C6Cl4I2·0.5C12H10N2, comprises planar sheets of the components held together by the combination of I...N halogen bonds and halogen–halogen contacts. Notably, the 1,2-C6I2Cl4 molecules π-stack in a homogeneous and face-to-face orientation that results in an infinite column of the halogen-bond donor. As a consequence of this stacking arrangement and I...N halogen bonds, molecules of BPE also stack in this type of pattern. In particular, neighbouring ethylene groups in BPE are found to be parallel and within the accepted distance for a photoreaction. Upon exposure to ultraviolet light, the cocrystal undergoes a solid-state [2 + 2] cycloaddition reaction that produces rctt-tetrakis(pyridin-4-yl)cyclobutane (TPCB) with an overall yield of 89%. A solvent-free approach utilizing dry vortex grinding of the components also resulted in a photoreactive material with a similar yield.

scholarly journals The Effect of Pressure on Halogen Bonding in 4-Iodobenzonitrile

Molecules ◽  
2019 ◽  
Vol 24 (10) ◽  
pp. 2018 ◽  
Author(s):  
Nico Giordano ◽  
Sergejs Afanasjevs ◽  
Christine M. Beavers ◽  
Claire L. Hobday ◽  
Konstantin V. Kamenev ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Halogen Bond ◽  
Ambient Pressure ◽  
Halogen Bonding ◽  
Optical Transmittance ◽  
Monoclinic Space Group ◽  
Ambient Conditions ◽  
Π Interactions ◽  
Transparent Crystal ◽  
Triclinic Phase

The crystal structure of 4-iodobenzonitrile, which is monoclinic (space group I2/a) under ambient conditions, contains chains of molecules linked through C≡N···I halogen-bonds. The chains interact through CH···I, CH···N and π-stacking contacts. The crystal structure remains in the same phase up to 5.0 GPa, the b axis compressing by 3.3%, and the a and c axes by 12.3 and 10.9 %. Since the chains are exactly aligned with the crystallographic b axis these data characterise the compressibility of the I···N interaction relative to the inter-chain interactions, and indicate that the halogen bond is the most robust intermolecular interaction in the structure, shortening from 3.168(4) at ambient pressure to 2.840(1) Å at 5.0 GPa. The π∙∙∙π contacts are most sensitive to pressure, and in one case the perpendicular stacking distance shortens from 3.6420(8) to 3.139(4) Å. Packing energy calculations (PIXEL) indicate that the π∙∙∙π interactions have been distorted into a destabilising region of their potentials at 5.0 GPa. The structure undergoes a transition to a triclinic ( P 1 ¯ ) phase at 5.5 GPa. Over the course of the transition, the initially colourless and transparent crystal darkens on account of formation of microscopic cracks. The resistance drops by 10% and the optical transmittance drops by almost two orders of magnitude. The I···N bond increases in length to 2.928(10) Å and become less linear [<C−I∙∙∙N = 166.2(5)°]; the energy stabilises by 2.5 kJ mol−1 and the mixed C-I/I..N stretching frequency observed by Raman spectroscopy increases from 249 to 252 cm−1. The driving force of the transition is shown to be relief of strain built-up in the π∙∙∙π interactions rather than minimisation of the molar volume. The triclinic phase persists up to 8.1 GPa.

Nontypical iodine–halogen bonds in the crystal structure of (3E)-8-chloro-3-iodomethylidene-2,3-dihydro-1,4-oxazino[2,3,4-ij]quinolin-4-ium triiodide

2016 ◽  
Vol 72 (4) ◽  
pp. 341-345 ◽  
Author(s):  
E. V. Bartashevich ◽  
V. I. Batalov ◽  
I. D. Yushina ◽  
A. I. Stash ◽  
Y. S. Chen
Keyword(s):  
Crystal Structure ◽  
Rare Case ◽  
Halogen Bond ◽  
Spectroscopic Properties ◽  
Halogen Bonds ◽  
X Ray Diffraction ◽  
Weakly Bound ◽  
X Ray ◽  
Raman Spectroscopic

Two kinds of iodine–iodine halogen bonds are the focus of our attention in the crystal structure of the title salt, C12H8ClINO+·I3−, described by X-ray diffraction. The first kind is a halogen bond, reinforced by charges, between the I atom of the heterocyclic cation and the triiodide anion. The second kind is the rare case of a halogen bond between the terminal atoms of neighbouring triiodide anions. The influence of relatively weakly bound iodine inside an asymmetric triiodide anion on the thermal and Raman spectroscopic properties has been demonstrated.

scholarly journals Azobenzene-based difunctional halogen-bond donor: towards the engineering of photoresponsive co-crystals

2013 ◽  
Vol 70 (1) ◽  
pp. 149-156 ◽  
Author(s):  
Marco Saccone ◽  
Giancarlo Terraneo ◽  
Tullio Pilati ◽  
Gabriella Cavallo ◽  
Arri Priimagi ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
X Ray Diffraction ◽  
Donor Molecule ◽  
X Ray ◽  
Covalent Interaction ◽  
Material Systems ◽  
Azo Group ◽  
Insight Into

Halogen bonding is emerging as a powerful non-covalent interaction in the context of supramolecular photoresponsive materials design, particularly due to its high directionality. In order to obtain further insight into the solid-state features of halogen-bonded photoactive molecules, three halogen-bonded co-crystals containing an azobenzene-based difunctional halogen-bond donor molecule, (E)-bis(4-iodo-2,3,5,6-tetrafluorophenyl)diazene, C12F8I2N2, have been synthesized and structurally characterized by single-crystal X-ray diffraction. The crystal structure of the non-iodinated homologue (E)-bis(2,3,5,6-tetrafluorophenyl)diazene, C12H2F8N2, is also reported. It is demonstrated that the studied halogen-bond donor molecule is a reliable tecton for assembling halogen-bonded co-crystals with potential photoresponsive behaviour. The azo group is not involved in any specific intermolecular interactions in any of the co-crystals studied, which is an interesting feature in the context of enhanced photoisomerization behaviour and photoactive properties of the material systems.

scholarly journals 1,3,5-Trifluoro-2,4,6-triiodobenzene–piperazine (2/1)

IUCrData ◽  
2021 ◽  
Vol 6 (10) ◽  
Author(s):  
Christelle Hajjar ◽  
Jeffrey S. Ovens ◽  
David L. Bryce
Keyword(s):  
Crystal Structure ◽  
Nitrogen Atom ◽  
Bond Angle ◽  
Halogen Bond ◽  
Covalent Bond ◽  
Halogen Bonding ◽  
The Other ◽  
Linear Interaction ◽  
Compound C ◽  
Van Der Waals Radii

The single-crystal structure of the title compound, C4H10N2·2C6F3I3, features a moderately strong halogen bond between one of the three crystallographically distinct iodine atoms and the nitrogen atom. The iodine–nitrogen distance is 2.820 (3) Å, corresponding to 80% of the sum of their van der Waals radii. The C—I...N halogen bond angle is 178.0 (1)°, consistent with the linear interaction of nitrogen via a σ-hole opposite the carbon–iodine covalent bond. The other two iodine atoms do not engage in halogen bonding. Some weak C—H...F and —H...I interactions are also observed. The complete piperazine molecule is generated by symmetry.

Redox reactive (RNC)CuII species stabilized in the solid state via halogen bond with I2

2018 ◽  
Vol 233 (6) ◽  
pp. 371-377 ◽  
Author(s):  
Margarita Bulatova ◽  
Anna A. Melekhova ◽  
Alexander S. Novikov ◽  
Daniil. M. Ivanov ◽  
Nadezhda A. Bokach
Keyword(s):  
Crystal Structure ◽  
Electron Density Distribution ◽  
Halogen Bond ◽  
Topological Analysis ◽  
Halogen Bonding ◽  
Molecular Iodine ◽  
X Ray Diffraction ◽  
Covalent Character ◽  
X Ray ◽  
Model Complex

AbstractThe crystal structure of [Cu2(μ-O)(μ-I)2(CNXyl)4]·I2(2·I2) was determined from single-crystal X-ray diffraction data. The adduct2·I2represents the first example of structurally characterized isocyanide-copper(II) complexes. In the structure of2·I2,2forms independent chains connected through molecular iodine via I···I–I···I halogen bonding. The DFT calculations and topological analysis of the electron density distribution within the formalism of Bader’s theory (QTAIM method) were performed for model complex2·I2and the obtained results allowed the attribution of these contacts to moderate strength (3.8–5.3 kcal/mol) non-covalent contacts exhibiting some covalent character.

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