Hydrogen bonds in the crystal structure of hydrophobic and hydrophilic COOH-functionalized imidazolium ionic liquids

CrystEngComm ◽  
2014 ◽  
Vol 16 (14) ◽  
pp. 3040-3046 ◽  
Author(s):  
Xiao-Peng Xuan ◽  
Liang-Liang Chang ◽  
Heng Zhang ◽  
Na Wang ◽  
Yang Zhao
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Ionic Liquids ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Carboxyl Group ◽  
Imidazolium Ionic Liquids

Hydrogen bonds such as the classic O–H⋯X (halide ion) hydrogen bond and the carboxyl group dimer were observed in the crystal structures of hydrophilic and hydrophobic COOH-functionalized imidazolium ionic liquids, respectively.

3-(4-Oxocyclohexyl)propionic acid monohydrate: hydrogen bonding in the hydrate of a ζ-keto acid

2007 ◽  
Vol 63 (3) ◽  
pp. o1173-o1175
Author(s):  
Stephanie M. Witko ◽  
Mark Davison ◽  
Hugh W. Thompson ◽  
Roger A. Lalancette
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Carboxyl Group ◽  
Keto Acid ◽  
Carbonyl Groups ◽  
O 178 ◽  
Network Of Hydrogen Bonds

In the title crystal structure, C9H14O3·H2O, the water molecule accepts a hydrogen bond from the carboxyl group [O...O = 2.6004 (13) Å and O—H...O = 163°], while donating hydrogen bonds to the ketone [O...O = 2.8193 (14) Å and O—H...O = 178 (2)°] and the acid carbonyl groups [O...O = 2.8010 (14) Å and O—H...O = 174 (2)°]. This creates a network of hydrogen bonds confined within a continuous flat ribbon two molecules in width and extending in the [101] direction.

scholarly journals Crystal structure ofrac-4-[2-(tert-butylazaniumyl)-1-hydroxyethyl]-2-(hydroxymethyl)phenol benzoate

2017 ◽  
Vol 73 (9) ◽  
pp. 1333-1335
Author(s):  
Wenju Liu ◽  
Qiliang Chen ◽  
Linda Yu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Dihedral Angle ◽  
Hydroxy Group ◽  
Carboxyl Group ◽  
Medium Strength ◽  
Benzoate Anion

The title salt, C13H22NO3+·C7H5O2−, comprises one salbutamol cation {systematic name: 4-[2-(tert-butylazaniumyl)-1-hydroxyethyl]-2-(hydroxymethyl)phenol} and a benzoate anion. The cation shows disorder of the hydroxy group [occupancy ratio 0.738 (3):0.262 (3)] at the stereogenic C atom. The non-planar benzoate anion [the dihedral angle between the benzene ring and the carboxyl group is 11.30 (8)°] is linked to the salbutamol cation by a medium-strength O—H...O hydrogen bond. Other intermolecular O—H...O and N—H...O hydrogen bonds of weaker nature give rise to [001] chains.

Hydrogen-bond coordination in organic crystal structures: statistics, predictions and applications

2014 ◽  
Vol 70 (1) ◽  
pp. 91-105 ◽  
Author(s):  
Peter T. A. Galek ◽  
James A. Chisholm ◽  
Elna Pidcock ◽  
Peter A. Wood
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Structural Stability ◽  
Statistical Models ◽  
Cambridge Structural Database ◽  
Acceptor Atom ◽  
Coordination Behaviour ◽  
Structural Database

Statistical models to predict the number of hydrogen bonds that might be formed by any donor or acceptor atom in a crystal structure have been derived using organic structures in the Cambridge Structural Database. This hydrogen-bond coordination behaviour has been uniquely defined for more than 70 unique atom types, and has led to the development of a methodology to construct hypothetical hydrogen-bond arrangements. Comparing the constructed hydrogen-bond arrangements with known crystal structures shows promise in the assessment of structural stability, and some initial examples of industrially relevant polymorphs, co-crystals and hydrates are described.

Crystal structure of tofacitinib dihydrogen citrate (Xeljanz®), (C16H21N6O)(H2C6H5O7)

2021 ◽  
pp. 1-8
Author(s):  
James A. Kaduk ◽  
Amy M. Gindhart ◽  
Thomas N. Blanton
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Powder Diffraction ◽  
Density Functional ◽  
Acid Group ◽  
Dimensional Network ◽  
Van Der Waals Contacts ◽  
Citrate Anion

The crystal structure of tofacitinib dihydrogen citrate (tofacitinib citrate) has been solved and refined using synchrotron X-ray powder diffraction data, and optimized using density functional techniques. Tofacitinib dihydrogen citrate crystallizes in space group P212121 (#19) with a = 5.91113(1), b = 12.93131(3), c = 30.43499(7) Å, V = 2326.411(6) Å3, and Z = 4. The crystal structure consists of corrugated layers perpendicular to the c-axis. Within the layers, cation⋯anion and anion⋯anion hydrogen bonds link the fragments into a two-dimensional network parallel to the ab-plane. Between the layers, there are only van der Waals contacts. A terminal carboxylic acid group in the citrate anion forms a strong charge-assisted hydrogen bond to the ionized central carboxylate group. The other carboxylic acid acts as a donor to the carbonyl group of the cation. The citrate hydroxy group forms an intramolecular charge-assisted hydrogen bond to the ionized central carboxylate. Two protonated nitrogen atoms in the cation act as donors to the ionized central carboxylate of the anion. These hydrogen bonds form a ring with the graph set symbol R2,2(8). The powder pattern has been submitted to ICDD® for inclusion in the Powder Diffraction File™ (PDF®).

6,9-Dibromo-2a,10b-diphenyl-2a,5,10,10b-tetrahydro-2H,3H-2,3,4a,10a-tetraazabenzo[g]cyclopenta[cd]azulene-1,4-dione monohydrate

2006 ◽  
Vol 62 (5) ◽  
pp. o1754-o1755
Author(s):  
Neng-Fang She ◽  
Sheng-Li Hu ◽  
Hui-Zhen Guo ◽  
An-Xin Wu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Title Compound ◽  
Supramolecular Structure ◽  
Hydrogen Bond Donor ◽  
Hydrogen Bond Acceptor ◽  
Compound C ◽  
Bifurcated Hydrogen Bond

The title compound, C24H18Br2N4O2·H2O, forms a supramolecular structure via N—H...O, O—H...O and C—H...O hydrogen bonds. In the crystal structure, the water molecule serves as a bifurcated hydrogen-bond acceptor and as a hydrogen-bond donor.

Crystal structure of osimertinib mesylate Form B (Tagrisso), (C28H34N7O2)(CH3O3S)

2021 ◽  
pp. 1-9
Author(s):  
James A. Kaduk ◽  
Nicholas C. Boaz ◽  
Emma L. Markun ◽  
Amy M. Gindhart ◽  
Thomas N. Blanton
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Powder Diffraction ◽  
Density Functional ◽  
Amino Nitrogen ◽  
Strong Hydrogen Bond ◽  
Powder Diffraction File ◽  
Dimethylamino Group ◽  
Intramolecular Hydrogen

The crystal structure of osimertinib mesylate Form B has been solved and refined using synchrotron X-ray powder diffraction data and optimized using density functional techniques. Osimertinib mesylate Form B crystallizes in space group P-1 (#2) with a = 11.42912(17), b = 11.72274(24), c = 13.32213(22) Å, α = 69.0265(5), β = 74.5914(4), γ = 66.4007(4)°, V = 1511.557(12) Å3, and Z = 2. The crystal structure is characterized by alternating layers of cation–anion and parallel stacking interactions parallel to the ab-planes. The cation is protonated at the nitrogen atom of the dimethylamino group, which forms a strong hydrogen bond between the cation and the anion. That hydrogen atom also participates in a weaker intramolecular hydrogen bond to an amino nitrogen. There are two additional N–H⋅⋅⋅O hydrogen bonds between the cation and the anion. Several C–H⋅⋅⋅O hydrogen bonds also link the cations and anions. The powder pattern has been submitted to ICDD® for inclusion in the Powder Diffraction File™.

Structure and properties of two new heteroleptic bismuth(III) dithiocabamates of the general composition Bi(S2CNH2)2X (X = Cl, SCN)

2022 ◽  
Vol 0 (0) ◽  
Author(s):  
Christoph Ludwig Teske ◽  
Huayna Terraschke ◽  
Sebastian Mangelsen ◽  
Wolfgang Bensch
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Electromagnetic Spectrum ◽  
Coordination Pattern ◽  
Structure And Properties ◽  
Acidic Solutions ◽  
Acetone Water ◽  
Asymmetric Coordination ◽  
3D Networks

Abstract The title compounds were prepared by precipitation from acidic solutions of the reactants in acetone/water. Bi(S2CNH2)2Cl (1) crystallizes in the non-centrosymmetric trigonal space group P32 with a = 8.6121(3) and c = 11.1554(4) Å, Z = 3; Bi(S2NH2)2SCN (2) in P21/c (monoclinic) with a = 5.5600(2), b = 14.3679(5), c = 12.8665(4) Å, and β = 90.37(3)°. In the crystal structure of 1 Bi3+ is in a sevenfold coordination of two bidentate and one monodentate S2CHNH2 − anions with an asymmetric coordination pattern of five Bi–S and two Bi–Cl− bonds. The linkage of these polyhedra via common Cl–S edges leads to a 1D polymeric structure with undulated chains propagating in the direction [001]. These chains are linked by strong and medium strong hydrogen bonds forming the 3D crystal structure. In the crystal structure of 2 the Bi3+ cation is in an eightfold coordination. The polyhedron can be described as a significantly distorted tetragonal anti-prism, capped by an additional S atom. Two of these prisms share a common quadrilateral face to form a “prism-double” (Bi2S10N2). These building units are linked by common edges, and the resulting 1D infinite angulated chains propagate along [100]. By contrast to organo-dithiocarbamate compounds, where C–H···X bridges are dominant, the interchain connections in the crystal structures of 1 and 2 are formed exclusively via N–H···S, N–H···Cl, and N–H···N interactions, generating the 3D networks. A significant eccentricity of the Bi3+ cation in the crystal structures of both complexes is observed. Both compounds emit light in the orange range of the electromagnetic spectrum.

scholarly journals Crystal structure of 2-methyl-N-{[2-(pyridin-2-yl)ethyl]carbamothioyl}benzamide

2015 ◽  
Vol 71 (9) ◽  
pp. o636-o636
Author(s):  
Nadiah Ameram ◽  
Farook Adam
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Thiourea Derivative ◽  
Π Interactions ◽  
Compound C ◽  
Benzene Rings ◽  
Ring Motif

In the title compound, C16H17N3OS, a benzoyl thiourea derivative, the planes of the pyridine and benzene rings are inclined to one another by 66.54 (9)°. There is an intramolecular N—H...O hydrogen bond present forming anS(6) ring motif. In the crystal, molecules are linkedviapairs of N—H...N hydrogen bonds, forming inversion dimers, which are reinforced by pairs of C—H...S hydrogen bonds. The dimers are linkedviaC—H...π interactions, forming ribbons along [010].

scholarly journals Crystal structure and hydrogen bonding in the water-stabilized proton-transfer salt brucinium 4-aminophenylarsonate tetrahydrate

2016 ◽  
Vol 72 (5) ◽  
pp. 751-755 ◽  
Author(s):  
Graham Smith ◽  
Urs D. Wermuth
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Network Structure ◽  
Three Dimensional ◽  
Water Molecules ◽  
Arsanilic Acid ◽  
Dimensional Network

In the structure of the brucinium salt of 4-aminophenylarsonic acid (p-arsanilic acid), systematically 2,3-dimethoxy-10-oxostrychnidinium 4-aminophenylarsonate tetrahydrate, (C23H27N2O4)[As(C6H7N)O2(OH)]·4H2O, the brucinium cations form the characteristic undulating and overlapping head-to-tail layered brucine substructures packed along [010]. The arsanilate anions and the water molecules of solvation are accommodated between the layers and are linked to them through a primary cation N—H...O(anion) hydrogen bond, as well as through water O—H...O hydrogen bonds to brucinium and arsanilate ions as well as bridging water O-atom acceptors, giving an overall three-dimensional network structure.

scholarly journals Crystal structure ofN-{4-[(6-chloropyridin-3-yl)methoxy]phenyl}-2,6-difluorobenzamide

2016 ◽  
Vol 72 (1) ◽  
pp. 60-62 ◽  
Author(s):  
Ying Liang ◽  
Li-Qiao Shi ◽  
Zi-Wen Yang
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Title Compound ◽  
Dihedral Angles ◽  
Π Interactions ◽  
Compound C

In the title compound, C19H13ClF2N2O2, the conformation of the N—H bond in the amide segment isantito the C=O bond. The molecule is not planar, with dihedral angles between the central benzene ring and the outer benzene and pyridyl rings of 73.35 (7) and 81.26 (6)°, respectively. A weak intramolecular C—H...O hydrogen bond occurs. In the crystal, N—H...N, C—H...O and C—H...F hydrogen bonds lead to the formation of dimers. The N—H...N inversion dimers are linked by π–π contacts between adjacent pyridine rings [centroid–centroid = 3.8541 (12) Å] and C—H...π interactions. These contacts combine to stack the molecules along theaaxis.

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