Co-Crystallisation of 1,4-Diiodotetrafluorobenzene with Three Different Symmetric Dipyridylacetylacetone Isomers Produces Four Halogen-Bonded Architectures

2017 ◽  
Vol 70 (5) ◽  
pp. 594 ◽  
Author(s):  
Joshua J. Brown ◽  
Aidan J. Brock ◽  
Michael C. Pfrunder ◽  
Julia P. Sarju ◽  
Abigail Z. Perry ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Halogen Bond ◽  
Three Dimensional ◽  
Halogen Bonding ◽  
Supramolecular Interactions ◽  
Ambient Conditions ◽  
Supramolecular Architectures ◽  
Crystallisation Behaviour ◽  
Π Stacking

The co-crystallisation behaviour of three symmetrical dipyridylacetylacetone ligands (1,3-di(2-pyridyl)-1,3-propanedione (o-bppdH), 1,3-di(3-pyridyl)-1,3-propanedione (m-bppdH), and 1,3-di(4-pyridyl)-1,3-propanedione (p-bppdH)), with the linear halogen-bond donor 1,4-diiodotetrafluorobenzene (1,4-DITFB) has been investigated. The reaction of these components under ambient conditions in a 1 : 1 stoichiometry produced four halogen-bonded assemblies ([o-bppdH·1,4-DITFB, [m-bppdH·1,4-DITFB], [2(m-bppdH)·1,4-DITFB], and [p-bppdH·1,4-DITFB]). The combination of multiple supramolecular interactions including halogen bonding, hydrogen bonding, and π-stacking produces a range of supramolecular architectures, including one-, two-, and three-dimensional motifs. The crystal structure of m-bppdH is also reported.

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.

scholarly journals Exploring the Halogen-Bonded Cocrystallization Potential of a Metal-Organic Unit Derived from Copper(ii) Chloride and 4-Aminoacetophenone

Materials ◽  
2020 ◽  
Vol 13 (10) ◽  
pp. 2385
Author(s):  
Vinko Nemec ◽  
Katarina Lisac ◽  
Marin Liović ◽  
Ivana Brekalo ◽  
Dominik Cinčić
Keyword(s):  
Hydrogen Bonding ◽  
Halogen Bond ◽  
Halogen Bonding ◽  
Building Blocks ◽  
Supramolecular Interactions ◽  
X Ray Diffraction ◽  
Square Planar ◽  
Metal Organic ◽  
Acetyl Group ◽  
Conventional Solution

In this work, we describe a novel halogen-bonded metal-organic cocrystal involving a square-planar Cu(ii) complex and 1,4-diiodotetrafluorobenzene (14tfib) by utilizing an amine ligand whose pendant acetyl group enables halogen bonding. The cocrystal was prepared by both mechanochemical synthesis (liquid-assisted grinding) and the conventional solution-based method. Crystal structure determination by single crystal X-ray diffraction revealed that the dominant supramolecular interactions are the I···O halogen bond between 14tfib and CuCl2(aap)2 building blocks, and the N–H···Cl hydrogen bonds between CuCl2(aap)2 molecules. The combination of halogen and hydrogen bonding leads to the formation of a 2D network. Overall, this work showcases an example of the possibility for extending the complexity of metal-organic crystal structures by using halogen bonding in a way that does not affect other hydrogen bonding synthons.

scholarly journals Redetermination of the crystal structure of 2-oxo-1,3-thiazolidin-4-iminium chloride

2019 ◽  
Vol 75 (4) ◽  
pp. 443-446
Author(s):  
Manickam Muthukkumar ◽  
Ammasai Karthikeyan ◽  
Madeshwaran Poovarasan ◽  
Vadivel Ruckmani ◽  
Dhanakotti Rajaram ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Three Dimensional ◽  
Chloride Anion ◽  
Supramolecular Interactions ◽  
Two Dimensional ◽  
Asymmetric Unit ◽  
Compound C ◽  
Dimensional Network ◽  
Supramolecular Chains

In the redetermination of the title compound, C3H5N2OS+·CI−, the asymmetric unit consists of one independent 2-oxo-1,3-thiazolidin-4-iminium cation and one independent chloride anion. The cation interacts with a chloride anion via N—H...Cl hydrogen bonds forming a supramolecular chain along [010]. These supramolecular chains are further extended by weak C—H...Cl and C—H...O interactions, forming a two-dimensional network parallel to (001). The crystal structure is further stabilized by weak C—O...π interactions, supporting a three-dimensional architecture. The structure was previously determined by Ananthamurthy & Murthy [Z. Kristallogr. (1975). 8, 356–367] but has been redetermined with higher precision to allow the hydrogen-bonding patterns and supramolecular interactions to be investigated.

scholarly journals Crystal structure of 4,4′-dibromo-2′,5′-dimethoxy-[1,1′-biphenyl]-2,5-dione (BrHBQBr)

2015 ◽  
Vol 71 (12) ◽  
pp. 1454-1456 ◽  
Author(s):  
Joseph E. Meany ◽  
Steven P. Kelley ◽  
Robert M. Metzger ◽  
Robin D. Rogers ◽  
Stephen A. Woski
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Dihedral Angle ◽  
Title Compound ◽  
Methoxy Group ◽  
Halogen Bonding ◽  
Stacking Interactions ◽  
Aromatic Rings ◽  
Compound C ◽  
Π Stacking

In the title compound, C14H10Br2O4, the dihedral angle between the aromatic rings is 67.29 (19)°. Both methoxy-group C atoms lie close to the plane of their attached ring [deviations = −0.130 (4) and 0.005 (5) Å]. In the crystal, molecules pack in a centrosymmetric fashion and interactviaa mixture of weak π–π stacking interactions [centroid–centoid separations = 4.044 (2) and 4.063 (3) Å], weak C—H...O hydrogen bonding, and Br...Br halogen bonding. This induces a geometry quite different than that predicted by theory.

scholarly journals Crystal structure of 2-bromo-1,4-dihydroxy-9,10-anthraquinone

2014 ◽  
Vol 70 (10) ◽  
pp. o1130-o1130 ◽  
Author(s):  
Wataru Furukawa ◽  
Munenori Takehara ◽  
Yoshinori Inoue ◽  
Chitoshi Kitamura
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Compound C ◽  
Π Stacking ◽  
Dimensional Network

In an attempt to brominate 1,4-dipropoxy-9,10-anthraquinone, a mixture of products, including the title compound, C14H7BrO4, was obtained. The molecule is essentially planar (r.m.s. deviation = 0.029 Å) and two intramolecular O—H...O hydrogen bonds occur. In the crystal, the molecules are linked by weak C—H...O hydrogen bonds, Br...O contacts [3.240 (5) Å], and π–π stacking interactions [shortest centroid–centroid separation = 3.562 (4) Å], generating a three-dimensional network.

3-n-Butyl-2-methoxy-1-benzothieno[3,2-d]pyrimidin-4(3H)-one

2006 ◽  
Vol 62 (4) ◽  
pp. o1319-o1320 ◽  
Author(s):  
Min-Hui Cao ◽  
Sheng-Zhen Xu ◽  
Yang-Gen Hu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Benzene Ring ◽  
Title Compound ◽  
Thiophene Ring ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Compound C ◽  
Π Stacking ◽  
Independent Molecules

The title compound, C15H16N2O2S, contains a five-membered thiophene ring fused to a benzene ring and a substituted pyrimidinone ring. All three rings in each of the independent molecules of the asymmetric unit lie in approximately the same plane. The crystal structure is stabilized by intermolecular C—H...O hydrogen bonding and π–π stacking interactions.

The crystal structure of gatehouseite

2011 ◽  
Vol 75 (6) ◽  
pp. 2823-2832
Author(s):  
P. Elliott ◽  
A. Pring
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Three Dimensional ◽  
Direct Methods ◽  
Chemical Analyses ◽  
X Ray Diffraction ◽  
X Ray ◽  
Manganese Phosphate ◽  
Phosphate Mineral ◽  
Unit Formula

AbstractThe crystal structure of the manganese phosphate mineral gatehouseite, ideally Mn52+(PO4)2(OH)4, space group P212121, a = 17.9733(18), b = 5.6916(11), c = 9.130(4) Å, V= 933.9(4) Å3, Z = 4, has been solved by direct methods and refined from single-crystal X-ray diffraction data (T = 293 K) to an R index of 3.76%. Gatehouseite is isostructural with arsenoclasite and with synthetic Mn52+(PO4)2(OH)4. The structure contains five octahedrally coordinated Mn sites, occupied by Mn plus very minor Mg with observed <Mn—O> distances from 2.163 to 2.239 Å. Two tetrahedrally coordinated P sites, occupied by P, Si and As, have <P—O> distances of 1.559 and 1.558 Å. The structure comprises two types of building unit. A strip of edge-sharing Mn(O,OH)6 octahedra, alternately one and two octahedra wide, extends along [010]. Chains of edge- and corner-shared Mn(O,OH)6 octahedra coupled by PO4 tetrahedra extend along [010]. By sharing octahedron and tetrahedron corners, these two units form a dense three-dimensional framework, which is further strengthened by weak hydrogen bonding. Chemical analyses by electron microprobe gave a unit formula of (Mn4.99Mg0.02)Σ5.01(P1.76Si0.07(As0.07)Σ2.03O8(OH)3.97.

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