scholarly journals Two 3-amino-1H-pyrazol-2-ium salts containing organic anions, and an orthorhombic polymorph of 3-amino-1H-pyrazol-2-ium nitrate

2021 ◽  
Vol 77 (1) ◽  
pp. 34-41
Author(s):  
Sreeramapura D. Archana ◽  
Channappa N. Kavitha ◽  
Hemmige S. Yathirajan ◽  
Sabine Foro ◽  
Christopher Glidewell
Keyword(s):  
Nitric Acid ◽  
Hydrogen Bonds ◽  
Fumaric Acid ◽  
Positive Charge ◽  
Three Dimensional ◽  
Organic Anions ◽  
Dilute Solution ◽  
Related Compounds

Co-crystallization from methanol of 3-amino-1H-pyrazole with 3,5-dinitrobenzoic acid produces 3-amino-1H-pyrazol-2-ium 3,5-dinitrobenzoate monohydrate, C3H6N3 +·C7H3N2O6 −·H2O, (I), while similar co-crystallization of this pyrazole with an equimolar quantity of fumaric acid produces bis(3-amino-1H-pyrazol-2-ium) fumarate–fumaric acid (1/1), 2C3H6N3 +·C4H2O4 2−·C4H4O4, (II). The reaction of 3-amino-1H-pyrazole with a dilute solution of nitric acid in methanol yields a second, orthorhombic polymorph of 3-amino-1H-pyrazol-2-ium nitrate, C3H6N3 +·NO3 −, (III). In each of (I)–(III), the bond distances in the cation provide evidence for extensive delocalization of the positive charge. In each of (I) and (II), an extensive series of O—H...O and N—H...O hydrogen bonds links the components into complex sheets, while in the structure of (III), the ions are linked by multiple N—H...O hydrogen bonds into a three-dimensional arrangement. Comparisons are made with the structures of some related compounds.

scholarly journals Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in zero, one, two and three dimensions

2020 ◽  
Vol 76 (11) ◽  
pp. 1779-1793
Author(s):  
Chayanna Harish Chinthal ◽  
Channappa N. Kavitha ◽  
Hemmige S. Yathirajan ◽  
Sabine Foro ◽  
Ravindranath S. Rathore ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Assembly ◽  
Organic Anions ◽  
Three Dimensions ◽  
Ribbon Structure ◽  
Related Compounds ◽  
Fumarate Salt

Fifteen 4-(2-methoxyphenyl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. In the isostructural 4-chlorobenzoate and 4-bromobenzoate salts, C11H17N2O+·C7H4ClO2 − (I) and C11H17N2O+·C7H4BrO2 − (II), and the 4-iodobenzoate salt C11H17N2O+·C7H4IO2 − (III), the ions are linked by N—H...O hydrogen bonds, forming centrosymmetric R 4 4(12) four-ion aggregates; a similar aggregate is formed in the 2-chlorobenzoate salt (V), isomeric with (I). In the 2-fluorobenzoate salt C11H17N2O+·C7H4FO2 − (IV), and the isomorphous pair of salts, the 2-bromobenzoate (VI), isomeric with (II) and 2-iodobenzoate (VII), isomeric with (III), N—H...O and C—H...π(arene) interactions link the components into three-dimensional arrays. Four-ion R 4 4(12) aggregates are also found in the 2-methylbenzoate, 4-aminobenzoate and 4-nitrobenzoate salts, C11H17N2O+·C8H7O2 − (VIII), C11H17N2O+·C7H6NO2 − (IX) and C11H17N2O+·C7H4NO4 − (X), but those in (IX) are linked into complex sheets by an additional N—H...O hydrogen bond. In the 3,5-dinitrobenzoate salt, C11H17N2O+·C7H3N2O6 −·2H2O (XI), N—H...O and O—H...O hydrogen bonds link the components into a complex ribbon structure. In the picrate salt, C11H17N2O+·C6H2N3O7 − (XII), the four-ion aggregates are linked into chains of rings by C—H...O hydrogen bonds. In the hydrogen maleate salt, C11H17N2O+·C4H3O4 − (XIII), two- and three-centre hydrogen bonds link the ions into a ribbon structure while both anions contain very short but asymmetric O—H...O hydrogen bonds, having O...O distances of 2.4447 (16) and 2.4707 (17) Å. O—H...O Hydrogen bonds link the anions in the hydrogen fumarate salt (XIV), isomeric with (XIII), into chains that are linked into sheets via N—H...O hydrogen bonds. In the hydrogen (2R,3R)-tartrate salt, C11H17N2O+·C4H5O6 −·1.698H2O (XV), the anions are linked into sheets by O—H...O hydrogen bonds. Comparisons are made with the structures of some related compounds.

scholarly journals Twelve 4-(4-methoxyphenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions

2019 ◽  
Vol 75 (10) ◽  
pp. 1494-1506 ◽  
Author(s):  
Haruvegowda Kiran Kumar ◽  
Hemmige S. Yathirajan ◽  
Sabine Foro ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Assembly ◽  
Organic Anions ◽  
Three Dimensions ◽  
Space Group ◽  
Dimensional Array ◽  
A Chain ◽  
Related Compounds

Twelve 4-(4-methoxyphenyl)piperazin-1-ium salts containing organic anions have been prepared and structurally characterized. The monohydrated benzoate, 4-fluorobenzoate, 4-chlorobenzoate and 4-bromobenzoate salts, C11H17N2O+·C7H5O2 −·H2O (I), C11H17N2O+·C7H4FO2 −·H2O (II), C11H17N2O+·C7H4ClO2 −·H2O (III), and C11H17N2O+·C7H4BrO2 −·H2O (IV), respectively, are isomorphous and all exhibit disorder in the 4-methoxyphenyl unit: the components are linked by N—H...O and O—H...O hydrogen bond to form chains of rings. The unsolvated 2-hydroxybenzoate, pyridine-3-carboxylate and 2-hydroxy-3,5-dinitrobenzoate salts, C11H17N2O+·C7H5O3 − (V), C11H17N2O+·C6H4NO2 − (VI) and C11H17N2O+·C7H3N2O7 − (VII), respectively, are all fully ordered: the components of (V) are linked by multiple N—H...O hydrogen bonds to form a chain of rings; those of (VI) are linked into a three-dimensional framework by a combination of N—H...O, C—H...O and C—H...N hydrogen bonds and those of (VII), where the anion has a structure reminiscent of the picrate anion, are linked into a three-dimensional array by N—H...O and C—H...O hydrogen bonds. The hydrogensuccinate and hydrogenfumarate salts, C11H17N2O+·C4H5O4 − (VIII) and C11H17N2O+·C4H3O3 − (IX), respectively, are isomorphous, and both exhibit disorder in the anionic component: N—H...O and O—H...O hydrogen bonds link the ions into sheets, which are further linked by C—H...π(arene) interactions. The anion of the hydrogenmaleate salt, C11H17N2O+·C4H3O3 − (X), contains a very short and nearly symmetrical O...H...O hydrogen bond, and N—H...O hydrogen bonds link the anions into chains of rings. The ions in the trichloroacetate salt, C11H17N2O+·C2Cl3O2 − (XI), are linked into simple chains by N—H...O hydrogen bonds. In the hydrated chloranilate salt, 2C11H17N2O+·C6Cl2O4 2−·2H2O (XII), which crystallizes as a non-merohedral twin, the anion lies across a centre of inversion in space group P21/n, and a combination of N—H...O and O—H...O hydrogen bonds generates complex sheets. Comparisons are made with the structures of some related compounds.

scholarly journals Crystal structure ofL-tryptophan–fumaric acid–water (1/1/1)

2015 ◽  
Vol 71 (9) ◽  
pp. o661-o662 ◽  
Author(s):  
M. Lydia Caroline ◽  
S. Kumaresan ◽  
P. G. Aravindan ◽  
M. Peer Mohamed ◽  
G. Mani
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Fumaric Acid ◽  
Solvent Molecule ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Acid Molecule ◽  
Water Solvent ◽  
Compound C ◽  
Tryptophan Molecule

In the title compound, C11H12N2O2·C4H4O4·H2O, the L-tryptophan molecule crystallized as a zwitterion, together with a neutral fumaric acid molecule and a water solvent molecule. In the crystal, the three components are linked by a series of N—H...O, O—H...O and C—H...O hydrogen bonds, forming slabs lying parallel to (001). The slabs are connected by O—H...O hydrogen bonds, involving inversion-related fumaric acid groups, leading to the formation of a three-dimensional structure.

Crystal structures and Hirshfeld surface analysis of four 1,4-bis(methoxyphenyl)-2,3-diazabuta-1,3-dienes: comparisons of the intermolecular interactions in related compounds

2019 ◽  
Vol 234 (1) ◽  
pp. 59-71 ◽  
Author(s):  
Ligia R. Gomes ◽  
John N. Low ◽  
Nathasha R. de L. Correira ◽  
Thais C.M. Noguiera ◽  
Alessandra C. Pinheiro ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Dimensional Structure ◽  
Intermolecular Hydrogen Bonds ◽  
Π Interactions ◽  
Isomeric Compound ◽  
Related Compounds

Abstract The crystal structures of four azines, namely 1-3-bis(4-methoxyphenyl)-2,3-diaza-1,4-butadiene, 1, 1,3-bis(2,3-dimethoxyphenyl)-2,3-diaza-1,4-butadiene, 2, 1,3-bis(2-hydroxy-3-methoxyphenyl)-2,3-diaza-1,4-butadiene, 3, and 1,3-bis(2-hydroxy-4-methoxyphenyl)-2,3-diaza-1,4-butadiene, 4, are reported. Molecules of 3 and 4, and both independent molecules of 2, Mol A and Mol B, possess inversion centers. The central C=N–N=C units in each molecule is planar with an (E,E) conformation. The intermolecular interactions found in the four compounds are C–H···O, C–H–N, C–H---π and π---π interactions. However, there is no consistent set of intermolecular interactions for the four compounds. Compound, 1, has a two-dimensional undulating sheet structure, generated from C–H···O and C–H···N intermolecular hydrogen bonds. The only recognized intermolecular interaction in 2 is a C–H···O hydrogen bond, which results in a zig-zag chain of alternating molecules, Mol A and Mol B. While 3 forms a puckered sheet of molecules, solely via C–H···π interactions, its isomeric compound, 4, has a more elaborate three-dimensional structure generated from a combination of C–H···O hydrogen bonds, C–H···π and π···π interactions. The findings in this study, based on both PLATON and Hirshfeld approaches, for the four representative compounds match well the reported structural findings in the literature of related compounds, which are based solely on geometric parameters.

Salts of maleic and fumaric acids with organic polyamines: comparison of isomeric acids as building blocks in supramolecular chemistry

2003 ◽  
Vol 59 (1) ◽  
pp. 100-117 ◽  
Author(s):  
Katharine F. Bowes ◽  
George Ferguson ◽  
Alan J. Lough ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Supramolecular Chemistry ◽  
Fumaric Acid ◽  
Maleic Acid ◽  
Rotation Axis ◽  
Three Dimensional ◽  
Building Blocks ◽  
Ionic Components ◽  
Acid Compound

Maleic acid and fumaric acid both readily form adducts with organic diamines: maleic acid usually forms 2:1 adducts with bases, while fumaric acid usually forms 1:1 adducts, and the supramolecular stuctures within the two series are not simply related. The 1:2 adducts formed by 1,2-bis(4-pyridyl)ethane and by 4,4′-bipyridyl, respectively, with maleic acid, compounds (1) and (2), are salts [{(diamine)H2}2+]·[(C4H3O4)−]2 in which the cations lie across a centre of inversion and a twofold rotation axis, respectively. The ions are linked by N—H...O hydrogen bonds into three-ion aggregates, which are further linked by C—H...O hydrogen bonds into two- and three-dimensional arrays, respectively. In the fumarate salts formed by 2,2′-dipyridylamine (1:1) and 1,4-diazabicyclo[2.2.2]octane (1:2), compounds (3) and (4), the ionic components are linked into molecular ladders. The 1:1 adduct of 4,4′-bipyridyl and fumaric acid, compound (5), contains two neutral components, both of which lie across centres of inversion; these components are linked into chains by a single O—H...N hydrogen bond and thence into sheets by C—H...O hydrogen bonds. The corresponding adduct formed by 1,4-diazabicyclo[2.2.2]octane, compound (6), is a salt that again contains chains linked into sheets by C—H...O hydrogen bonds. In the 1:1 adducts, compounds (7), (8) and (10), that are formed between 1,2-bis(4-pyridyl)ethane, 4,4′-trimethylenedipyridine and hexamethylenetetramine, respectively, with fumaric acid, and in the 1:2 adduct, compound (9), of 2,2′-dipyridylamine and maleic acid, the chains that are generated by the hard hydrogen bonds are linked by C—H...O hydrogen bonds to form, in each case, a single three-dimensional framework. In the 1:1 adduct, compound (11), of 2,2′-bipyridyl and fumaric acid the hydrogen bonds generate two interwoven three-dimensional frameworks.

A hydrogen-bonded tetramer in (2RS,4SR)-7-bromo-2-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-naphtho[1,2-b]azepin-4-ol and a three-dimensional hydrogen-bonded framework in (2RS,4SR)-2-(3-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1H-naphtho[1,2-b]azepin-4-ol

2013 ◽  
Vol 69 (4) ◽  
pp. 448-452 ◽  
Author(s):  
Andrés F. Yépes ◽  
Alirio Palma ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Space Groups ◽  
Dimensional Array ◽  
Compound Ii ◽  
Related Compounds ◽  
Hydrogen Bonded

(2RS,4SR)-7-Bromo-2-(2-methylphenyl)-2,3,4,5-tetrahydro-1H-naphtho[1,2-b]azepin-4-ol, C21H20BrNO, (I), and (2RS,4SR)-2-(3-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1H-naphtho[1,2-b]azepin-4-ol, C19H19NOS, (II), both crystallize withZ′ = 2 in the space groupsP21/candCc, respectively; compound (II) crystallizes as a nonmerohedral twin, with twin fractions 0.183 (2) and 0.817 (2). The molecules of (I) are linked by O—H...O and O—H...N hydrogen bonds to form a cyclic centrosymmetricR44(16) tetramer. The molecules of (II) are linked by O—H...O hydrogen bonds to form aC22(4) chain and these chains are weakly linked by a single C—H...π(thienyl) interaction to form a three-dimensional array. Comparisons are made with some related compounds.

Interplay of hydrogen bonds, iodo...nitro interactions and aromatic π...π stacking interactions in iodo-nitroanilines

2002 ◽  
Vol 58 (4) ◽  
pp. 701-709 ◽  
Author(s):  
Simon J. Garden ◽  
Silvia P. Fontes ◽  
James L. Wardell ◽  
Janet M. S. Skakle ◽  
John N. Low ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Nitro Group ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Single Type ◽  
Stacking Interactions ◽  
Π Stacking ◽  
Independent Molecules ◽  
Related Compounds ◽  
Centrosymmetric Dimers

Molecules of 2-iodo-5-nitroaniline (I) are linked by N—H...O hydrogen bonds into centrosymmetric dimers and by asymmetric three-centre iodo...nitro interactions into chains, so forming chains of fused centrosymmetric rings: these chains are linked by aromatic π...π stacking interactions to form a three-dimensional structure. In the isomeric 4-iodo-2-nitroaniline (II), each of the two independent molecules forms hydrogen-bonded chains that are linked by two-centre iodo...nitro interactions into sheets of two types, each containing only a single type of molecule: π...π stacking interactions are absent. In 2,4-diiodo-3-nitroaniline (III), where the nitro group is almost orthogonal to the aryl ring, a combination of N—H...O hydrogen bonds and two distinct two-centre iodo...nitro interactions links the molecules into a three-dimensional framework that is reinforced by aromatic π...π stacking interactions. Bond lengths and conformations are discussed and comparisons are drawn with related compounds.

scholarly journals Different patterns of supramolecular assembly in constitutionally similar 6-arylimidazo[2,1-b][1,3,4]thiadiazoles

2014 ◽  
Vol 70 (9) ◽  
pp. 920-926 ◽  
Author(s):  
Aletti S. Praveen ◽  
Hemmige S. Yathirajan ◽  
Manpreet Kaur ◽  
Badiadka Narayana ◽  
Eric C. Hosten ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Reaction Times ◽  
Supramolecular Assembly ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Aryl Group ◽  
Π Stacking ◽  
Related Compounds ◽  
Centrosymmetric Dimers

Four imidazo[2,1-b][1,3,4]thiadiazoles containing a simply-substituted 6-aryl group have been synthesized by reaction of 2-amino-1,3,4-thiadiazoles with bromoacetylarenes using microwave irradiation and brief reaction times. 6-(2-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H6ClN3S, (I), 6-(2-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C11H8ClN3S, (II), 6-(3,4-dichlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H5Cl2N3S, (III), and 6-(4-fluoro-3-methoxyphenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C12H10FN3OS, (IV), crystallize withZ′ values of 2, 1, 1 and 2 respectively. The molecular skeletons are all nearly planar and the dihedral angles between the imidazole and aryl rings are 1.51 (8) and 7.28 (8)° in (I), 9.65 (7)° in (II), 10.44 (8)° in (III), and 1.05 (8) and 7.21 (8)° in (IV). The molecules in (I) are linked by three independent C—H...N hydrogen bonds to form ribbons containing alternatingR22(8) andR44(18) rings, and these ribbons are linked into a three-dimensional array by three independent π-stacking interactions. Both (II) and (III) contain centrosymmetric dimers formed by π-stacking interactions but hydrogen bonds are absent, and the molecules of (IV) are linked into centrosymmetricR22(8) dimers by C—H...N hydrogen bonds. Comparisons are made with a number of related compounds.

Kinetic behaviour investigations and crystal structure of nitric acid dihydrate

2001 ◽  
Vol 57 (1) ◽  
pp. 27-35 ◽  
Author(s):  
N. Lebrun ◽  
F. Mahe ◽  
J. Lamiot ◽  
M. Foulon ◽  
J. C. Petit ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Nitric Acid ◽  
Hydrogen Bonds ◽  
Single Crystal ◽  
Three Dimensional ◽  
Thermal Conditions ◽  
Kinetic Behaviour ◽  
Hydrogen Bond Networks ◽  
Atomic Distance

X-ray powder diffraction experiments are performed to prove the possible crystallization of nitric acid dihydrate (HNO3·2H2O, further denoted NAD) and to determine the best thermal conditions for growing a single crystal. It is shown that the kinetic behaviour of NAD strongly depends on the preliminary thermal treatment. One good single crystal obtained by an in situ adapted Bridgman method procedure enabled determination of the crystal structure. The intensities of diffracted lines with h odd are all very weak. The H atom of nitric acid is delocalized to one water molecule leading to an association of equimolar nitrate (NO3 −) and an H5O2 + ionic group. The asymmetric unit contains two such molecules. These two molecules are related by a pseudo a/2 translation (with a 0.3 Å mean atomic distance difference), except for one H atom of the water molecules (0.86 Å) because of their different orientations in the two molecules. The two molecules, linked by very strong hydrogen bonds, are arranged in layers. Two layers which are linked by weaker hydrogen bonds are approximately oriented along the c axis. The structure may be described by translations of this set of two layers along the c axis without hydrogen bonds leading to a two-dimensional hydrogen-bond network. The structures of the monohydrate (NAM) and trihydrate (NAT) are re-determined for comparisons. These structures may be described by one- and three-dimensional hydrogen-bond networks, respectively.

scholarly journals Three 4-(4-fluorophenyl)piperazin-1-ium salts containing organic anions: supramolecular assembly in one, two and three dimensions

2020 ◽  
Vol 76 (6) ◽  
pp. 841-847 ◽  
Author(s):  
Chayanna Harish Chinthal ◽  
Hemmige S. Yathirajan ◽  
Sreeramapura D. Archana ◽  
Sabine Foro ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Assembly ◽  
Organic Anions ◽  
Three Dimensions ◽  
Carboxyl Groups ◽  
Rotation Symmetry ◽  
Independent Components ◽  
Multiple Hydrogen Bonds

Three salts containing the 4-(4-fluorophenyl)piperazin-1-ium cation have been prepared and structurally characterized. In 4-(4-fluorophenyl)piperazin-1-ium 2-hydroxy-3,5-dinitrobenzoate, C10H14FN2 +·C7H3N2O7 −, (I), the anion contains an intramolecular O—H...O hydrogen bond, and it has a structure similar to that of the picrate ion. The cations and anions are linked into [001] chains of rings by a combination of two three-centre N—H...(O)2 hydrogen bonds. The anion in 4-(4-fluorophenyl)piperazin-1-ium hydrogen oxalate, C10H14FN2 +·C2HO4 −, (II), is planar, and the cations and anions are linked into (100) sheets by multiple hydrogen bonds including two-centre N—H...O, three-centre N—H...(O)2, O—H...O, C—H...O and C—H...π(arene) types. In 4-(4-fluorophenyl)piperazin-1-ium hydrogen (2R,3R)-tartrate monohydrate, C10H14FN2 +·C4H5O6 −·H2O, (III), the anion exhibits an approximate non-crystallographic twofold rotation symmetry with antiperiplanar carboxyl groups. A combination of eight hydrogen bonds, encompassing two- and three-centre N—H...O systems, O—H...O and C—H...π(arene) types, link the independent components into a three-dimensional framework. Comparisons are made with some related structures.

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