The crystalline forms of nine hydrochloride salts of substituted tryptamines

2021 ◽  
Vol 77 (10) ◽  
pp. 615-620
Author(s):  
Duyen N. K. Pham ◽  
Zachary S. Belanger ◽  
Andrew R. Chadeayne ◽  
James A. Golen ◽  
David R. Manke
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Two Dimensional ◽  
One Dimensional ◽  
Hydrogen Bonding Networks ◽  
Hydrogen Bonding Network ◽  
Crystalline Forms

The crystal structures of the hydrochloride salts of nine substituted tryptamines, namely, 1-methyltryptammonium chloride, C11H15N2 +·Cl−, (1), 2-methyl-1-phenyltryptammonium chloride, C17H19N2 +·Cl−, (2), 5-methoxytryptammonium chloride, C11H15N2O+·Cl−, (3), 5-bromotryptammonium chloride, C10H12BrN2 +·Cl−, (4), 5-chlorotryptammonium chloride, C10H12ClN2 +·Cl−, (5), 5-fluorotryptammonium chloride, C10H12FN2 +·Cl−, (6), 5-methyltryptammonium chloride, C11H15N2 +·Cl−, (7), 6-fluorotryptammonium chloride, C10H12FN2 +·Cl−, (8), and 7-methyltryptammonium chloride, C11H15N2 +·Cl−, (9), are reported. The seven tryptamines with N—H indoles, (3)–(9), show very similar structures, with N—H...Cl hydrogen-bonding networks forming two-dimensional sheets in the crystals. These sheets are combinations of R 4 2(8) and R 4 2(18) rings, and C 2 1(4) and C 2 1(9) chains. Substitution at the indole N atom reduces the dimensionality of the hydrogen-bonding network, with compounds (1) and (2) demonstrating one-dimensional chains that are a combination of different rings and parallel chains.

scholarly journals Crystal structures ofN′-aminopyridine-2-carboximidamide andN′-{[1-(pyridin-2-yl)ethylidene]amino}pyridine-2-carboximidamide

2017 ◽  
Vol 73 (7) ◽  
pp. 1021-1025
Author(s):  
Francois Eya'ane Meva ◽  
Timothy John Prior ◽  
David John Evans ◽  
Emmanuel Roland Mang
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Dimensional Chain ◽  
Two Dimensional ◽  
One Dimensional ◽  
Bond Lengths ◽  
Hydrogen Bonding Interactions ◽  
Hydrogen Bonding Network

The crystal structures ofN′-aminopyridine-2-carboximidamide (C6H8N4),1, andN′-{[1-(pyridin-2-yl)ethylidene]amino}pyridine-2-carboximidamide (C13H13N5),2, are described. The non-H atoms in compound1are nearly planar (r.m.s. deviation from planarity = 0.0108 Å), while2is twisted about the central N—N bond by 17.8 (2)°. Both molecules are linked by intermolecular N—H...N hydrogen-bonding interactions;1forms a two-dimensional hydrogen-bonding network and for2the network is a one-dimensional chain. The bond lengths of these molecules are similar to those in other literature reports of azine and diimine systems.

Cocrystals of 6-methyl-2-thiouracil: presence of the acceptor–donor–acceptor/donor–acceptor–donor synthon

2015 ◽  
Vol 71 (3) ◽  
pp. 229-238 ◽  
Author(s):  
Wilhelm Maximilian Hützler ◽  
Ernst Egert
Keyword(s):  
Hydrogen Bonding ◽  
Antithyroid Drug ◽  
Two Dimensional ◽  
Orientational Disorder ◽  
One Dimensional ◽  
Donor Acceptor ◽  
Hydrogen Bonding Network ◽  
Hydrogen Bonding Site ◽  
Uracil Base ◽  
Bonding Site

The results of seven cocrystallization experiments of the antithyroid drug 6-methyl-2-thiouracil (MTU), C5H6N2OS, with 2,4-diaminopyrimidine, 2,4,6-triaminopyrimidine and 6-amino-3H-isocytosine (viz.2,6-diamino-3H-pyrimidin-4-one) are reported. MTU features anADA(A= acceptor andD= donor) hydrogen-bonding site, while the three coformers show complementaryDADhydrogen-bonding sites and therefore should be capable of forming anADA/DADN—H...O/N—H...N/N—H...S synthon with MTU. The experiments yielded one cocrystal and six cocrystal solvates, namely 6-methyl-2-thiouracil–2,4-diaminopyrimidine–1-methylpyrrolidin-2-one (1/1/2), C5H6N2OS·C4H6N4·2C5H9NO, (I), 6-methyl-2-thiouracil–2,4-diaminopyrimidine (1/1), C5H6N2OS·C4H6N4, (II), 6-methyl-2-thiouracil–2,4-diaminopyrimidine–N,N-dimethylacetamide (2/1/2), 2C5H6N2OS·C4H6N4·2C4H9NO, (III), 6-methyl-2-thiouracil–2,4-diaminopyrimidine–N,N-dimethylformamide (2/1/2), C5H6N2OS·0.5C4H6N4·C3H7NO, (IV), 2,4,6-triaminopyrimidinium 6-methyl-2-thiouracilate–6-methyl-2-thiouracil–N,N-dimethylformamide (1/1/2), C4H8N5+·C5H5N2OS−·C5H6N2OS·2C3H7NO, (V), 6-methyl-2-thiouracil–6-amino-3H-isocytosine–N,N-dimethylformamide (1/1/1), C5H6N2OS·C4H6N4O·C3H7NO, (VI), and 6-methyl-2-thiouracil–6-amino-3H-isocytosine–dimethyl sulfoxide (1/1/1), C5H6N2OS·C4H6N4O·C2H6OS, (VII). Whereas in cocrystal (I) anR22(8) interaction similar to the Watson–Crick adenine/uracil base pair is formed and a two-dimensional hydrogen-bonding network is observed, the cocrystals (II)–(VII) contain the triply hydrogen-bondedADA/DADN—H...O/N—H...N/N—H...S synthon and show a one-dimensional hydrogen-bonding network. Although 2,4-diaminopyrimidine possesses only oneDADhydrogen-bonding site, it is, due to orientational disorder, triply connected to two MTU molecules in (III) and (IV).

scholarly journals Crystal structures, Hirshfeld atom refinements and Hirshfeld surface analyses of tris(4,5-dihydrofuran-2-yl)methylsilane and tris(4,5-dihydrofuran-2-yl)phenylsilane

2020 ◽  
Vol 76 (9) ◽  
pp. 1514-1519
Author(s):  
Anna Krupp ◽  
Eva Rebecca Barth ◽  
Rana Seymen ◽  
Carsten Strohmann
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Surface Analysis ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Supramolecular Network ◽  
Two Dimensional ◽  
One Dimensional ◽  
Atom Model ◽  
Hydrogen Bonding Interactions

The title compounds, C13H18O3Si (1) and C18H20O3Si (2), represent functionalizable dihydrofuranylsilanes, which permit substitution by a variety of nucleophiles. The crystal structures of 1 and 2 display weak intermolecular C—H...O hydrogen-bonding interactions (quantified by Hirshfeld surface analysis), leading to a two-dimensional supramolecular network for 1 and a one-dimensional supramolecular network for 2. The crystal structures of 1 and 2 were refined both on the basis of the independent atom model (IAM) and the Hirshfeld atom refinement (HAR) approach, and the results are comparatively discussed.

Assembly of C-propyl-pyrogallol[4]arene with bipyridine-based spacers and solvent molecules

2020 ◽  
Vol 75 (4) ◽  
pp. 341-345
Author(s):  
Xiao-Li Liu ◽  
Jing-Long Liu ◽  
Hong-Mei Yang ◽  
Ai-Quan Jia ◽  
Qian-Feng Zhang
Keyword(s):  
Mixed Solvent ◽  
Polymer Structure ◽  
Brick Wall ◽  
Two Dimensional ◽  
One Dimensional ◽  
X Ray ◽  
X Ray Crystallography ◽  
Wave Trough ◽  
Hydrogen Bonding Networks ◽  
Solvent Molecules

AbstractCo-crystallization of C-propyl-pyrogallol[4]arene (PgC3) with 4,4′-bipyridine (bpy) in ethanol afforded a multi-component complex (PgC3) · 3(bpy) ·(EtOH) (1) that consists of a one-dimensional brick-wall framework, which was formed by four pyrogallol[4]arene molecules and two juxtaposed bpy molecules, entrapping two other bpy molecules as guests within each cavity. Heating a mixture of PgC3 and trans-1,2-bis-(4-pyridyl)ethylene (bpe) in an ethanol-water mixed solvent allowed the isolation of a multi-component complex (PgC3) ·(bpe) · 2(EtOH) ·(H2O) (2), which has a two-dimensional wave-like polymer structure with the bpe molecules embedded in the wave trough between two PgC3 molecules. Single-crystal X-ray crystallography was utilized to investigate the hydrogen bonding networks of the multi-component complexes 1 and 2.

Hydrogen-bonding networks of purine derivatives and their bilayers for guest intercalation

CrystEngComm ◽  
2016 ◽  
Vol 18 (1) ◽  
pp. 62-67
Author(s):  
Yoona Jang ◽  
Seo Yeon Yoo ◽  
Hye Rin Gu ◽  
Yu Jin Lee ◽  
Young Shin Cha ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Two Dimensional ◽  
Purine Derivatives ◽  
Guest Molecules ◽  
Π Interactions ◽  
Hydrogen Bonding Networks ◽  
Hydrogen Bonded

6-Chloro-9-propyl-purin-2-amine (pr-GCl) forms two-dimensional hydrogen-bonded networks which in turn stack via π–π interactions, leading to the formation of bilayers that can accommodate organic guest molecules.

scholarly journals Crystal structures of 4-chloropyridine-2-carbonitrile and 6-chloropyridine-2-carbonitrile exhibit different intermolecular π-stacking, C—H...Nnitrileand C—H...Npyridineinteractions

2015 ◽  
Vol 71 (7) ◽  
pp. 852-856 ◽  
Author(s):  
Matthew J. Montgomery ◽  
Thomas J. O'Connor ◽  
Joseph M. Tanski
Keyword(s):  
Solid State ◽  
Crystal Structures ◽  
Pyridine Ring ◽  
Nitrile Group ◽  
Two Dimensional ◽  
One Dimensional ◽  
Face To Face ◽  
Π Stacking

The two title compounds are isomers of C6H3ClN2containing a pyridine ring, a nitrile group, and a chloro substituent. The molecules of each compound pack together in the solid state with offset face-to-face π-stacking, and intermolecular C—H...Nnitrileand C—H...Npyridineinteractions. 4-Chloropyridine-2-carbonitrile, (I), exhibits pairwise centrosymmetric head-to-head C—H...Nnitrileand C—H...Npyridineinteractions, forming one-dimensional chains, which are π-stacked in an offset face-to-face fashion. The intermolecular packing of the isomeric 6-chloropyridine-2-carbonitrile, (II), which differs only in the position of the chloro substituent on the pyridine ring, exhibits head-to-tail C—H...Nnitrileand C—H...Npyridineinteractions, forming two-dimensional sheets which are π-stacked in an offset face-to-face fashion. In contrast to (I), the offset face-to-face π-stacking in (II) is formed between molecules with alternating orientations of the chloro and nitrile substituents.

Polymorphs of phenazine hexacyanoferrate(II) hydrate: supramolecular isomerism in a 2D hydrogen-bonded network

2021 ◽  
Vol 77 (2) ◽  
pp. 211-218
Author(s):  
Ivica Cvrtila ◽  
Vladimir Stilinović
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
The Other ◽  
Two Dimensional ◽  
Structural Motifs ◽  
Supramolecular Isomerism ◽  
Other Hand ◽  
Π Stacking ◽  
Hydrogen Bonded

The crystal structures of two polymorphs of a phenazine hexacyanoferrate(II) salt/cocrystal, with the formula (Hphen)3[H2Fe(CN)6][H3Fe(CN)6]·2(phen)·2H2O, are reported. The polymorphs are comprised of (Hphen)2[H2Fe(CN)6] trimers and (Hphen)[(phen)2(H2O)2][H3Fe(CN)6] hexamers connected into two-dimensional (2D) hydrogen-bonded networks through strong hydrogen bonds between the [H2Fe(CN)6]2− and [H3Fe(CN)6]− anions. The layers are further connected by hydrogen bonds, as well as through π–π stacking of phenazine moieties. Aside from the identical 2D hydrogen-bonded networks, the two polymorphs share phenazine stacks comprising both protonated and neutral phenazine molecules. On the other hand, the polymorphs differ in the conformation, placement and orientation of the hydrogen-bonded trimers and hexamers within the hydrogen-bonded networks, which leads to different packing of the hydrogen-bonded layers, as well as to different hydrogen bonding between the layers. Thus, aside from an exceptional number of symmetry-independent units (nine in total), these two polymorphs show how robust structural motifs, such as charge-assisted hydrogen bonding or π-stacking, allow for different arrangements of the supramolecular units, resulting in polymorphism.

scholarly journals Investigation of glycerol hydrogen-bonding networks in choline chloride/glycerol eutectic-forming liquids using neutron diffraction

2019 ◽  
Vol 21 (39) ◽  
pp. 21782-21789 ◽  
Author(s):  
Adam H. Turner ◽  
John D. Holbrey
Keyword(s):  
Hydrogen Bonding ◽  
Neutron Diffraction ◽  
Neutron Scattering ◽  
Choline Chloride ◽  
Three Dimensional ◽  
Hydrogen Bonding Networks ◽  
Hydrogen Bonding Network

Neutron scattering reveals the persistent three-dimensional hydrogen-bonding network between glycerol molecules in the 1 : 2 choline chloride/glycerol eutectic.

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