Investigation of polar crystalline materials containing hydrochlorothiazide: electron density distribution and optical properties

2021 ◽  
Vol 77 (6) ◽  
Author(s):  
Joanna Wojnarska ◽  
Marlena Gryl ◽  
Tomasz Seidler ◽  
Katarzyna Marta Stadnicka
Keyword(s):  
Optical Properties ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Electron Density ◽  
Intermolecular Interactions ◽  
Second Harmonic ◽  
Functional Materials ◽  
Linear Birefringence ◽  
Structure Property ◽  
Second Harmonic Generation Efficiency

The polar hydrochlorothiazide polymorph (I) (systematic name: 6-chloro-1,1-dioxo-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide, C7H8ClN3O4S2) and, recently designed by us, the polar 2-aminopyridine hydrochlorothiazide water <1/1/1> (C7H8ClN3O4S2·C5H6N2·H2O), (II), have been investigated. The crystal structures of both materials were determined using the single-crystal X-ray diffraction technique. The intermolecular interactions in (I) and (II) were studied in detail via topological electron-density analysis. The obtained results showed hydrogen bonds with a character intermediate between closed-shell and shared-shell in both crystal structures. The most important hydrogen bonds in (I) are formed between sulfonamide groups, whereas in (II), water molecules play a crucial role as they interconnect 2-aminopyridine and hydrochlorothiazide molecules. Calculations of the optical properties revealed that both materials exhibit large linear birefringence, twice that of calcite. The theoretically predicted second harmonic generation efficiency is four times and five times larger than that of KH2PO4 for (I) and (II), respectively. The information gathered on intermolecular interactions and structure–property correlations was used to identify the best strategies for the future design of new functional materials of this kind.

scholarly journals L-alaninium perrhenate: crystal structure and non-linear optical properties

2014 ◽  
Vol 12 (10) ◽  
pp. 1016-1022 ◽  
Author(s):  
Vitor Rodrigues ◽  
Maria Costa ◽  
Etelvina Gomes ◽  
Dmitry Isakov ◽  
Michael Belsley
Keyword(s):  
Crystal Structure ◽  
Optical Properties ◽  
Second Harmonic ◽  
Negative Ions ◽  
Damage Threshold ◽  
Linear Optics ◽  
Second Harmonic Generation Efficiency ◽  
Non Linear ◽  
Linear Optical Properties ◽  
Linear Optical

AbstractThe crystal structure and non-linear optical properties of L-alaninium perrhenate, C3H8NO2+ ReO4 −, are reported. The protonated amino acid and the perrhenate anion have their usual geometries. The three-dimensional hydrogen-bonded network can be seen as a stacking of layers parallel to the (100) planes. Each layer is formed by chains of alternating positive and negative ions along the b and c axes. Hydrogen bonding of adjacent layers forms alternating chains along the a axis. A high damage threshold and a second-harmonic generation efficiency three times that of KDP make this new material potentially useful in non-linear optics.

scholarly journals Crystal structures of (2E)-1-(3-bromothiophen-2-yl)-3-(2-methoxyphenyl)prop-2-en-1-one and (2E)-1-(3-bromothiophen-2-yl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one

2015 ◽  
Vol 71 (8) ◽  
pp. 965-971 ◽  
Author(s):  
Vasant S. Naik ◽  
Venkataraya Shettigar ◽  
Tyler S. Berglin ◽  
Jillian S. Coburn ◽  
Jerry P. Jasinski ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Intramolecular Interaction ◽  
Intramolecular Interactions ◽  
Inversion Symmetry ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Space Group ◽  
Independent Molecules

In the molecules of the title compounds, (2E)-1-(3-bromo-thiophen-2-yl)-3-(2-methoxyphenyl)prop-2-en-1-one, C14H11BrO2S, (I), which crystallizes in the space groupP-1 with four independent molecules in the asymmetric unit (Z′ = 8), and (2E)-1-(3-bromothiophen-2-yl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one, C15H13BrO3S, (II), which crystallizes withZ′ = 8 in the space groupI2/a, the non-H atoms are nearly coplanar. The molecules of (I) pack with inversion symmetry stacked diagonally along thea-axis direction. Weak C—H...Br intramolecular interactions in each of the four molecules in the asymmetric unit are observed. In (II), weak C—H...O, bifurcated three-center intermolecular interactions forming dimers along with weak C—H...π and π–π stacking interactions are observed, linking the molecules into sheets along [001]. A weak C—H...Br intramolecular interaction is also present. There are no classical hydrogen bonds present in either 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.

A topological analysis of the interion interactions of tetraphenylphosphonium squarate

2006 ◽  
Vol 84 (5) ◽  
pp. 804-811 ◽  
Author(s):  
David Wolstenholme ◽  
Manuel AS Aquino ◽  
T Stanley Cameron ◽  
Joseph D Ferrara ◽  
Katherine N Robertson
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Electron Density ◽  
Intermolecular Interactions ◽  
Critical Points ◽  
Topological Analysis ◽  
Van Der Waals ◽  
Van Der Waals Interactions ◽  
Multipole Refinement ◽  
Diverse Interactions

The tetraphenylphosphonium squarate salt crystallizes with a number of diverse interactions, which all have the potential to be classified as hydrogen bonds. The squarate anions are found as dimers linked by O-H···O interactions. The multipole refinement of the tetraphenylphosphonium squarate was performed using the Hansen–Coppens model followed by topological analysis of its intermolecular interactions. A total of 28 interactions were found among the symmetry related molecules, which include a number of C-H···Cπ, C-H···O, and C-H···H-C interactions, along with the O-H···O interaction. With the criteria for hydrogen bonding proposed by Popelier and Koch, it is possible to determine which of these interactions are hydrogen bonds and which are van der Waals interactions. Both linear and exponentially dependent correlations can be seen for the properties of the bond critical points involving the intermolecular interactions that fulfill these criteria. All this leads to a better understanding of the role that hydrogen bonds play in the formation of small organic compounds.Key words: electron density, multiple refinement, hydrogen bonds.

Bases, solvates and salts: new benzimidazole- and pyridine-scaffolded ligands

2020 ◽  
Vol 76 (4) ◽  
pp. 367-374
Author(s):  
Aleksandra Bocian ◽  
Adam Gorczyński ◽  
Dawid Marcinkowski ◽  
Grzegorz Dutkiewicz ◽  
Violetta Patroniak ◽  
...  
Keyword(s):  
Schiff Base ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Stabilization Energy ◽  
Interaction Energies ◽  
Free Base ◽  
Schiff Base Ligands ◽  
Π Interactions ◽  
Charged Ligands

The intermolecular interactions in the structures of a series of Schiff base ligands have been thoroughly studied. These ligands can be obtained in different forms, namely, as the free base 2-[(2E)-2-(1H-imidazol-4-ylmethylidene)-1-methylhydrazinyl]pyridine, C10H11N5, 1, the hydrates 2-[(2E)-2-(1H-imidazol-2-ylmethylidene)-1-methylhydrazinyl]-1H-benzimidazole monohydrate, C12H12N6·H2O, 2, and 2-{(2E)-1-methyl-2-[(1-methyl-1H-imidazol-2-yl)methylidene]hydrazinyl}-1H-benzimidazole 1.25-hydrate, C13H14N6·1.25H2O, 3, the monocationic hydrate 5-{(1E)-[2-(1H-1,3-benzodiazol-2-yl)-2-methylhydrazinylidene]methyl}-1H-imidazol-3-ium trifluoromethanesulfonate monohydrate, C12H13N6 +·CF3O3S−·H2O, 5, and the dicationic 2-{(2E)-1-methyl-2-[(1H-imidazol-3-ium-2-yl)methylidene]hydrazinyl}pyridinium bis(trifluoromethanesulfonate), C10H13N5 2+·2CF3O3S−, 6. The connection between the forms and the preferred intermolecular interactions is described and further studied by means of the calculation of the interaction energies between the neutral and charged components of the crystal structures. These studies show that, in general, the most important contribution to the stabilization energy of the crystal is provided by π–π interactions, especially between charged ligands, while the details of the crystal architecture are influenced by directional interactions, especially relatively strong hydrogen bonds. In one of the structures, a very interesting example of the nontypical F...O interaction was found and its length, 2.859 (2) Å, is one of the shortest ever reported.

Different supramolecular architectures mediated by different weak interactions in the crystals of three N-aryl-2,5-dimethoxybenzenesulfonamides

2017 ◽  
Vol 73 (10) ◽  
pp. 833-844 ◽  
Author(s):  
K. Shakuntala ◽  
S. Naveen ◽  
N. K. Lokanath ◽  
P. A. Suchetan ◽  
M. Abdoh
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Weak Interactions ◽  
Three Dimensional ◽  
Shape Index ◽  
Intramolecular Interactions ◽  
Molecular Conformations ◽  
Supramolecular Architectures ◽  
The Relationship

The synthesis and evaluation of the pharmacological activities of molecules containing the sulfonamide moiety have attracted interest as these compounds are important pharmacophores. The crystal structures of three closely related N-aryl-2,5-dimethoxybenzenesulfonamides, namely N-(2,3-dichlorophenyl)-2,5-dimethoxybenzenesulfonamide, C14H13Cl2NO4S, (I), N-(2,4-dichlorophenyl)-2,5-dimethoxybenzenesulfonamide, C14H13Cl2NO4S, (II), and N-(2,4-dimethylphenyl)-2,5-dimethoxybenzenesulfonamide, C16H19NO4S, (III), are described. The asymmetric unit of (I) consists of two symmetry-independent molecules, while those of (II) and (III) contain one molecule each. The molecular conformations are stabilized by different intramolecular interactions, viz. C—H...O interactions in (I), N—H...Cl and C—H...O interactions in (II), and C—H...O interactions in (III). The crystals of the three compounds display different supramolecular architectures built by various weak intermolecular interactions of the types C—H...O, C—H...Cl, C—H...π(aryl), π(aryl)–π(aryl) and Cl...Cl. A detailed Hirshfeld surface analysis of these compounds has also been conducted in order to understand the relationship between the crystal structures. The d norm and shape-index surfaces of (I)–(III) support the presence of various intermolecular interactions in the three structures. Analysis of the fingerprint plots reveals that the greatest contribution to the Hirshfeld surfaces is from H...H contacts, followed by H...O/O...H contacts. In addition, comparisons are made with the structures of some related compounds. Putative N—H...O hydrogen bonds are observed in 29 of the 30 reported structures, wherein the N—H...O hydrogen bonds form either C(4) chain motifs or R 2 2(8) rings. Further comparison reveals that the characteristics of the N—H...O hydrogen-bond motifs, the presence of other interactions and the resultant supramolecular architecture is largely decided by the position of the substituents on the benzenesulfonyl ring, with the nature and position of the substituents on the aniline ring exerting little effect. On the other hand, the crystal structures of (I)–(III) display several weak interactions other than the common N—H...O hydrogen bonds, resulting in supramolecular architectures varying from one- to three-dimensional depending on the nature and position of the substituents on the aniline ring.

Crystal structures and Hirshfeld surface analyses of a des-A-B-aromatic steroidal compound, and two of its derivatives, having a trans-2,3,4,5-tetrahydro-3a-methyl-7-methoxybenz[e]indane skeleton – structural comparisons with reported tetrahydrobenz[e]indene derivatives

2019 ◽  
Vol 74 (9) ◽  
pp. 649-663
Author(s):  
Ligia R. Gomes ◽  
John N. Low ◽  
Alan B. Turner ◽  
Alexander W. Nowicki ◽  
Thomas C. Baddeley ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Hirshfeld Surface ◽  
Dimensional Structure ◽  
Monoclinic Space Group ◽  
Asymmetric Unit ◽  
Space Group ◽  
Π Interactions ◽  
Independent Molecules

AbstractThe crystal structures and Hirshfeld surface analyses of the des-A-B-aromatic steroid derivative, (3a,9b)-1,2,3a,4,5,9b-hexahydro-7-methoxy-3a-methyl-3H-benz[e]-inden-3-one (or 5-methoxy-des-A-estra-5,7,9-triene-17-one) 1, its acetohydrazide derivative, 2, and its hydrazone derivative, 3, are reported. All three compounds crystallize in chiral space groups: compounds 1 and 2 in the orthorhombic space group P212121 each with one molecule in the asymmetric unit, and compound 3 in the monoclinic space group P21 with two similar but independent molecules, Mol A and Mol B, in the asymmetric unit. Both the five-membered and six-membered non-aromatic rings in all three compounds have envelope or near envelope shapes. In compounds 2 and 3 the N=N units have (E)-arrangements. The intermolecular interactions in crystals of compound 1 are C–H · · · O hydrogen bonds and C–H · · · π interactions, in compound 2 N–H · · · O and C–H · · · O hydrogen bonds and C–H · · · π interactions are present, while in compound 3 there are just C–H · · · π interactions. An important substructure in 1 is a sheet of molecules, composed of ${\rm{R}}_6^6(44)$ rings, formed from C–H · · · O(methoxy) and C–H · · · O(carbonyl) hydrogen bonds, the molecules of which form columns linked via the B and D rings, i.e. in a head-to-tail fashion. Compound 2 is an acylhydrazonyl compound, in which the two independent molecules are linked into asymmetric dimers via strong classical N–H · · · O hydrogen bonds, with the formation of ${\rm{R}}_2^2(8)$ rings. In both 1 and 2, further intermolecular interactions result in 3-dimensional structures, while compound 3 has a 1-dimensional structure arising from C–H · · · O interactions generating spiral chains. The results have been compared with existing data.

Structural insight from intermolecular interactions and energy framework analyses of 2-substituted 6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-ones

2021 ◽  
Vol 77 (3) ◽  
Author(s):  
Akmaljon G. Tojiboev ◽  
Burkhon Zh. Elmuradov ◽  
Halima Mouhib ◽  
Kambarali K. Turgunov ◽  
Askar Sh. Abdurazakov ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Gas Phase ◽  
Intermolecular Interactions ◽  
Correction Term ◽  
Three Dimensional ◽  
Dispersion Interactions ◽  
Additional Information ◽  
Experimental Crystal ◽  
The Impact

The crystal structures of three mackinazolinone derivatives (2-amino-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one at room temperature, and 2-nitro-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one and N-(11-oxo-6,8,9,11-tetrahydro-7H-pyrido[2,1-b]quinazolin-2-yl)benzamide at 100 K) are explored using X-ray crystallography. To delineate the different intermolecular interactions and the respective interaction energies in the crystal architectures, energy framework analyses were carried out using the CE-B3LYP/6-31G(d,p) method implemented in the CrystalExplorer software. In the structures the different molecules are linked by C—H...O, C—H...N and N—H...O hydrogen bonds. Together with these hydrogen bonds, C—H...π and C—O...π interactions are involved in the formation of a three-dimensional crystal network. A Hirshfeld surface analysis allows the visualization of the two-dimensional fingerprint plots and the quantification of the contributions of H...H, H...C/C...H and H...O/O...H contacts throughout the different crystal structures. To obtain additional information on the intrinsic properties of our targets and to compare the experimental crystal structures with their respective conformations in the gas phase, quantum chemical calculations at the B3LYP-D3BJ/6-311++G(d,p) level of theory, including Grimme's D3 correction term and BJ damping functions, were carried out to account for intramolecular dispersion interactions. The identified energy gaps between the highest occupied and the lowest unoccupied molecular orbitals (HOMO–LUMO gap) of our targets in the gas phase and in two implicit solvents (methanol and dimethyl sulfoxide) allow us to quantify the impact of different substituents on the reactivity of mackinazolinone derivatives.

scholarly journals Supramolecular organization of complexes of aryl hydrazones with SnCl3and SnCl4

2014 ◽  
Vol 70 (a1) ◽  
pp. C657-C657
Author(s):  
Alexander Korlyukov ◽  
Anna Vologzhanina ◽  
Evgenia Voronova ◽  
Natalia Shmatkova ◽  
Inna Seifullina
Keyword(s):  
Crystal Structures ◽  
Electron Density ◽  
Intermolecular Interactions ◽  
Active Species ◽  
Biologically Active ◽  
Supramolecular Organization ◽  
Halogen Bonds ◽  
Covalent Interaction ◽  
Theoretical Approaches ◽  
Density Analysis

Chelate complexes of main group metals with N,O-chelating Schiff Base ligands have been reported as perspective models for biologically active species. The derivatives of aryl hydrazones are among the most widely used ligands of such type. In our study, crystal structures of aryl hydrazones with SnCl3and SnCl4are discussed: the presence of aromatic fragments, amine groups and chlorine atoms therein are responsible for the coexistence of strong hydrogen and halogen bonds as well as stacking and Cl...π interactions. Interplay between these types of interactions and their role in stabilization of crystal structures is the subject of particular interest. We studied all these aspects in complexes of aryl hydrazones using different theoretical approaches: those based on Stockholder partitioning, molecular electrostatic potential, non-covalent interaction index, AIM theory – together with Espinosa-Mollins-Lecomte correlation to estimate the energy of all intermolecular interactions in crystals by means of electron density analysis from periodic quantum chemical calculations (VASP code). Our results showed that the presence of intermolecular interactions led to a noticeable redistribution of electron density in crystal as compared to an isolated molecule. Although Cl...π, stacking interactions and halogen bonds are numerous in the crystals of these complexes, their contribution to the energy of their crystal lattice does not exceed 30%. The work was supported by Council of the President of the Russian Federation (grant MD-3589.2014.3).

scholarly journals Crystal structures of (E)-(3-ethyl-1-methyl-2,6-diphenylpiperidin-4-ylidene)amino phenyl carbonate and (E)-(3-isopropyl-1-methyl-2,6-diphenylpiperidin-4-ylidene)amino phenyl carbonate

2014 ◽  
Vol 70 (10) ◽  
pp. 199-202 ◽  
Author(s):  
B. Raghuvarman ◽  
R. Sivakumar ◽  
V. Thanikachalam ◽  
S. Aravindhan
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angle ◽  
Intermolecular Interactions ◽  
Three Dimensional ◽  
Piperidine Ring ◽  
Dihedral Angles ◽  
Π Interactions ◽  
Dimensional Network ◽  
Phenyl Rings

In the title compounds, C27H28N2O3, (I), and C28H30N2O3, (II), the conformation about the C=N bond isE. The piperidine rings adopt chair conformations with the attached phenyl rings almost normal to their mean planes, the dihedral angles being 85.82 (8) and 85.84 (7)° in (I), and 87.98 (12) and 86.42 (13)° in (II). The phenyl rings are inclined to one another by 52.87 (8)° in (I) and by 60.51 (14)° in (II). The main difference in the conformation of the two compounds is the angle of inclination of the phenoxycarbonyl ring to the piperidine ring mean plane. In (I), these two planes are almost coplanar, with a dihedral angle of 2.05 (8)°, while in (II), this angle is 45.24 (13)°. In the crystal of (I), molecules are linked by C—H...O hydrogen bonds, forming inversion dimers withR22(14) loops. The dimers are linkedviaC—H...π interactions forming a three-dimensional network. In the crystal of (II), there are no significant intermolecular interactions present.

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