scholarly journals Crystal structures of hibiscus acid and hibiscus acid dimethyl ester isolated fromHibiscus sabdariffa(Malvaceae)

2017 ◽  
Vol 73 (9) ◽  
pp. 1368-1371 ◽  
Author(s):  
Ahmed M. Zheoat ◽  
Alexander I. Gray ◽  
John O. Igoli ◽  
Alan R. Kennedy ◽  
Valerie A. Ferro
Keyword(s):  
Hydrogen Bonding ◽  
Dimethyl Sulfoxide ◽  
Dimethyl Ester ◽  
Biologically Active ◽  
Hibiscus Sabdariffa ◽  
Compound I ◽  
One Dimensional ◽  
Acid Dimethyl Ester ◽  
Solvent Molecules ◽  
Compound Ii

The biologically active title compounds have been isolated fromHibiscus sabdariffaplants, hibiscus acid as a dimethyl sulfoxide monosolvate [systematic name: (2S,3R)-3-hydroxy-5-oxo-2,3,4,5-tetrahydrofuran-2,3-dicarboxylic acid dimethyl sulfoxide monosolvate], C6H6O7·C2H6OS, (I), and hibiscus acid dimethyl ester [systematic name: dimethyl (2S,3R)-3-hydroxy-5-oxo-2,3,4,5-tetrahydrofuran-2,3-dicarboxylate], C8H10O7, (II). Compound (I) forms a layered structure with alternating layers of lactone and solvent molecules, that include a two-dimensional hydrogen-bonding construct. Compound (II) has two crystallographically independent and conformationally similar molecules per asymmetric unit and forms a one-dimensional hydrogen-bonding construct. The known absolute configuration for both compounds has been confirmed.

Synthesis and crystal structures of some bis(3-methyl-1H-indol-2-yl)(salicyl)methanes

2019 ◽  
Vol 75 (1) ◽  
pp. 65-69
Author(s):  
Wyatt Cole ◽  
Stephanie L. Hemmingson ◽  
Audrey C. Eisenberg ◽  
Catherine A. Ulman ◽  
Joseph M. Tanski ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Dimethyl Sulfoxide ◽  
Crystal Structures ◽  
Double Layer ◽  
Acid Catalysis ◽  
Double Layers ◽  
One Dimensional ◽  
Salicylaldehyde Derivatives ◽  
Central Carbon ◽  
Solvent Molecules

Four 2,2′-bisindolylmethanes (BIMs), a useful class of polyindolyl species joined to a central carbon, were synthesized using salicylaldehyde derivatives and simple acid catalysis; these are 2-[bis(3-methyl-1H-indol-2-yl)methyl]-6-methylphenol, (IIa), 2-[bis(3-methyl-1H-indol-2-yl)methyl]-4,6-dichlorophenol, (IIb), 2-[bis(3-methyl-1H-indol-2-yl)methyl]-4-nitrophenol, (IIc), and 2-[bis(3-methyl-1H-indol-2-yl)methyl]-4,6-di-tert-butylphenol, (IId). BIMs (IIa) and (IIb) were characterized crystallographically as the dimethyl sulfoxide (DMSO) disolvates, i.e. C26H24N2O·2C2H6OS and C25H20Cl2N2O·2C2H6OS, respectively. Both form strikingly similar one-dimensional hydrogen-bonding chain motifs with the DMSO solvent molecules. BIM (IIa) packs into double layers of chains whose orientations alternate every double layer, while (IIb) forms more simply packed chains along the a axis. BIM (IIa) has a remarkably long c axis.

Hydrogen bonding due to regioisomerism and its effect on the supramolecular architecture of diethyl 2-[(2/4-hydroxyanilino)methylidene]malonates

2012 ◽  
Vol 69 (1) ◽  
pp. 70-73 ◽  
Author(s):  
Andivelu Ilangovan ◽  
Perumal Venkatesan ◽  
Rajendran Ganesh Kumar
Keyword(s):  
Hydrogen Bonding ◽  
Intramolecular Hydrogen Bonding ◽  
Mirror Plane ◽  
Supramolecular Architecture ◽  
Intermolecular Hydrogen Bonding ◽  
Compound I ◽  
Monoclinic Crystal ◽  
One Dimensional ◽  
Intramolecular Hydrogen ◽  
Compound Ii

Diethyl 2-[(2-hydroxyanilino)methylidene]malonate, (I), and diethyl 2-[(4-hydroxyanilino)methylidene]malonate, (II), both C14H17NO5, crystallize in centrosymmetric orthorhombic and monoclinic crystal systems, respectively. Compound (I) resides on a crystallographic mirror plane and displays bifurcated intramolecular hydrogen bonding, as well as intermolecular hydrogen bonding due to the position of the hydroxy group. Compound (II) has a single intramolecular N—H...O hydrogen bond. Infinite one-dimensional head-to-tail chains formed by O—H...O hydrogen bonding are present in both structures. The molecular packing is mainly influenced by the intermolecular O—H...O interactions. Additionally, C—H...O interactions crosslinking the chains are found in (II).

ZnIIand CuIIcomplexes generated from 5-(pyridin-4-yl)-3-[2-(pyridin-4-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione

2013 ◽  
Vol 69 (7) ◽  
pp. 716-720 ◽  
Author(s):  
Hang-Ju Zhao ◽  
Jian-Ping Ma ◽  
Qi-Kui Liu ◽  
Yu-Bin Dong
Keyword(s):  
Coordination Polymer ◽  
Stacking Interactions ◽  
The Novel ◽  
Two Dimensional ◽  
Compound I ◽  
Coordination Environment ◽  
Dimensional Network ◽  
Solvent Molecules ◽  
Compound Ii ◽  
Nitrate Anions

A new 1,3,4-oxadiazole-containing bispyridyl ligand, namely 5-(pyridin-4-yl)-3-[2-(pyridin-4-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione (L), has been used to create the novel complexes tetranitratobis{μ-5-(pyridin-4-yl)-3-[2-(pyridin-4-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione}zinc(II), [Zn2(NO3)4(C14H12N4OS)2], (I), andcatena-poly[[[dinitratocopper(II)]-bis{μ-5-(pyridin-4-yl)-3-[2-(pyridin-4-yl)ethyl]-1,3,4-oxadiazole-2(3H)-thione}] nitrate acetonitrile sesquisolvate dichloromethane sesquisolvate], {[Cu(NO3)(C14H12N4OS)2]NO3·1.5CH3CN·1.5CH2Cl2}n, (II). Compound (I) presents a distorted rectangular centrosymmetric Zn2L2ring (dimensions 9.56 × 7.06 Å), where each ZnIIcentre lies in a {ZnN2O4} coordination environment. These binuclear zinc metallocycles are linked into a two-dimensional network through nonclassical C—H...O hydrogen bonds. The resulting sheets lie parallel to theacplane. Compound (II), which crystallizes as a nonmerohedral twin, is a coordination polymer with double chains of CuIIcentres linked by bridgingLligands, propagating parallel to the crystallographicaaxis. The CuIIcentres adopt a distorted square-pyramidal CuN4O coordination environment with apical O atoms. The chains in (II) are interlinkedviatwo kinds of π–π stacking interactions along [0\overline 11]. In addition, the structure of (II) contains channels parallel to the crystallographicadirection. The guest components in these channels consist of dichloromethane and acetonitrile solvent molecules and uncoordinated nitrate anions.

Two nickel(II) bis[(pyridin-2-yl)methyl]amine complexes with homophthalic and benzene-1,2,4,5-tetracarboxylic acids

2014 ◽  
Vol 70 (6) ◽  
pp. 541-546 ◽  
Author(s):  
Ana María Atria ◽  
Maria Teresa Garland ◽  
Ricardo Baggio
Keyword(s):  
Water Molecules ◽  
Charge Balance ◽  
Compound I ◽  
Carboxylate Ligands ◽  
Crystal Water ◽  
One Dimensional ◽  
Bridging Ligand ◽  
Methyl Amine ◽  
Compound Ii ◽  
Bonding Scheme

Two new NiIIcomplexes involving the ancillary ligand bis[(pyridin-2-yl)methyl]amine (bpma) and two different carboxylate ligands,i.e.homophthalate [hph; systematic name: 2-(2-carboxylatophenyl)acetate] and benzene-1,2,4,5-tetracarboxylate (btc), namelycatena-poly[[aqua{bis[(pyridin-2-yl)methyl]amine-κ3N,N′,N′′}nickel(II)]-μ-2-(2-carboxylatophenyl)aceteto-κ2O:O′], [Ni(C9H6O4)(C12H13N3)(H2O)]n, and (μ-benzene-1,2,4,5-tetracarboxylato-κ4O1,O2:O4,O5)bis(aqua{bis[(pyridin-2-yl)methyl]amine-κ3N,N′,N′′}nickel(II)) bis(triaqua{bis[(pyridin-2-yl)methyl]amine-κ3N,N′,N′′}nickel(II)) benzene-1,2,4,5-tetracarboxylate hexahydrate, [Ni2(C10H2O8)(C12H13N3)2(H2O)2]·[Ni(C12H13N3)(H2O)3]2(C10H2O8)·6H2O, (II), are presented. Compound (I) is a one-dimensional polymer with hph acting as a bridging ligand and with the chains linked by weak C—H...O interactions. The structure of compound (II) is much more complex, with two independent NiIIcentres having different environments, one of them as part of centrosymmetric [Ni(bpma)(H2O)]2(btc) dinuclear complexes and the other in mononuclear [Ni(bpma)(H2O)3]2+cations which (in a 2:1 ratio) provide charge balance for btc4−anions. A profuse hydrogen-bonding scheme, where both coordinated and crystal water molecules play a crucial role, provides the supramolecular linkage of the different groups.

Crystal structure and hydrogen bonding in the hydrated cocrystalline salt tryptaminium–3,5-dinitrobenzoate–quinoline–water (3/3/2/2)

2016 ◽  
Vol 72 (10) ◽  
pp. 738-742 ◽  
Author(s):  
Daniel E. Lynch ◽  
Graham Smith ◽  
Tony D. Keene ◽  
Peter N. Horton
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Crystal Packing ◽  
Ternary Systems ◽  
Causative Factor ◽  
Asymmetric Unit ◽  
One Dimensional ◽  
Solvent Molecules ◽  
Ring Centroid ◽  
Low Symmetry

The study of ternary systems is interesting because it introduces the concept of molecular preference/competition into the system where one molecule may be displaced because the association between the other two is significantly stronger. Current definitions of a tertiary system indicate that solvent molecules are excluded from the molecule count of the system and some of the latest definitions state that any molecule that is not a solid in the parent form at room temperature should also be excluded from the molecule count. In the structure of the quinoline adduct hydrate of tryptaminium 3,5-dinitrobenzoate, 3C10H13N2+·3C7H3N2O6−·2C9H7N·2H2O, the asymmetric unit comprises multiple cation and anion species which are conformationally similar among each type set. In the crystal, a one-dimensional hydrogen-bonded supramolecular structure is generated through extensive intra- and inter-unit aminium N—H...O and N—H...N, and water O—H...O hydrogen bonds. Within the central-core hydrogen-bonding associations, conjoined cyclicR44(10),R53(10) andR44(12) motifs are generated. The unit is expanded into a one-dimensional column-like polymer extending along [010]. Present also in the crystal packing of the structure are a total of 19 π–π interactions involving both cation, anion and quinoline species [ring-centroid separation range = 3.395 (3)–3.797 (3) Å], as well as a number of weak C—H...O hydrogen-bonding associations. The presence of the two water molecules in the crystal structure is considered to be the principal causative factor in the low symmetry of the asymmetric unit.

scholarly journals Six tris(bipyridyl)iron(II) complexes with 2-substituted 1,1,3,3-tetracyanopropenide, perchlorate and tetrafluoridoborate anions; order versus disorder, hydrogen bonding and C—N...π interactions

2018 ◽  
Vol 74 (12) ◽  
pp. 1717-1726
Author(s):  
Abderezak Addala ◽  
Zouaoui Setifi ◽  
Yukio Morimoto ◽  
Beñat Artetxe ◽  
Takashi Matsumoto ◽  
...  
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Compound I ◽  
Π Interactions ◽  
Chain Compounds ◽  
Compound Ii ◽  
Ionic Components

Structures are reported for six closely related salts of tris(bipyridyl)iron(II) cations, namely tris(2,2′-bipyridine)iron(II) bis(1,1,3,3-tetracyano-2-methoxypropenide) 0.776-hydrate, [Fe(C10H8N2)3](C8H3N4O)2.0.776H2O, (I), tris(2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(propylsulfanyl)propenide perchlorate, [Fe(C10H8N2)3](C10H7N4S)(ClO4), (II), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-methoxypropenide tetrafluoridoborate ethanol 0.926-solvate, [Fe(C12H12N2)3](C8H3N4O)(BF4).0.926C2H2O, (III), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-ethoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4O)(BF4), (IV), tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-(ethylsufanyl)propenide tetrafluoridoborate, [Fe(C12H12N2)3](C9H5N4S)(BF4), (V), and tris(5,5′-dimethyl-2,2′-bipyridine)iron(II) 1,1,3,3-tetracyano-2-propoxypropenide tetrafluoridoborate, [Fe(C12H12N2)3](C10H7N4O)(BF4), (VI). In compound (I), one of the anions is disordered over two sets of atomic sites with equal occupancies while, in the second anion, just one of the C(CN)2 units is disordered, again over two sets of atomic sites with equal occupancies: the anionic components are linked by multiple C—H...N hydrogen bonds to form a three-dimensional framework. In compound (II), the polynitrile anion is disordered over two sets of atomic sites with occupancies in the approximate ratio 3:1, while the perchlorate anion is disordered over three sets of atomic sites: there are C—N...π interactions between the cations and the polynitrile anion. The polynitrile anion in compound (III) is fully ordered, but the tetrafluoridoborate anion is disordered over two sets of atomic sites with occupancies 0.671 (4) and 0.329 (4): the cations and the tetrafluoridoborate anions are linked by C—H...F interactions to form an interrupted chain. Compounds (IV) and (V) are isostructural and all of the ionic components are fully ordered in both of them: the cations and tetrafluoridoborate anions are linked into C 2 2(12) chains. The polynitrile anion in compound (VI) is disordered over two sets of atomic sites with approximately equal occupancies, and here the chains formed by the cations and the tetrafluoridoborate anions are of the C 2 2(13) type.

Syntheses and crystal structures of two heterometallic iodoplumbates containing mixed-valence copper(I/II)

2017 ◽  
Vol 73 (12) ◽  
pp. 1098-1103 ◽  
Author(s):  
Le-Qing Fan ◽  
Xiao-Tong Zhu
Keyword(s):  
Mixed Valence ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Compound I ◽  
One Dimensional ◽  
Face To Face ◽  
Hydrogen Bonding Interactions ◽  
Compound Ii ◽  
Solvothermal Conditions ◽  
Phenanthroline Ligands

Mixed-valence copper(I/II) atoms have been introduced successfully into a Pb/I skeleton to obtain two heterometallic iodoplumbates, namely poly[bis(tetra-n-butylammonium) [bis(μ3-dimethyldithiocarbamato)dodeca-μ3-iodido-hexa-μ2-iodido-tetracopper(I)copper(II)hexalead(II)]], {(C16H36N)2[Cu4 ICuIIPb6(C3H6NS2)2I18]} n , (I), and poly[[μ3-iodido-tri-μ2-iodido-iodido[bis(1,10-phenanthroline)copper(I)]copper(I)copper(II)lead(II)] hemiiodine], {[CuICuIIPbI5(C12H8N2)2]·0.5I2} n , (II), under solution and solvothermal conditions, respectively. Compound (I) contains two-dimensional anionic layers, which are built upon the linkages of CuII(S2CNMe2)2 units and one-dimensional anionic Pb/I/CuI chains. Tetra-n-butylammonium cations are located between the anionic layers and connected to them via C—H...I hydrogen-bonding interactions. Compound (II) exhibits a one-dimensional neutral structure, which is composed of [PbI5] square pyramids, [CuII4] tetrahedra and [CuIIN4I] trigonal bipyramids. Face-to-face aromatic π–π stacking interactions between adjacent 1,10-phenanthroline ligands stabilize the structure and assemble compound (II) into a three-dimensional supramolecular structure. I2 molecules lie in the voids of the structure.

scholarly journals Structural characterization of hydrogen bonding for antipyrine derivatives: Single-crystal X-ray diffraction and theoretical studies

2021 ◽  
Vol 16 (2) ◽  
pp. 113-137
Author(s):  
N. S. Rukk ◽  
R. S. Shamsiev ◽  
D. V. Albov ◽  
S. N. Mudretsova
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Electron Density ◽  
Bond Formation ◽  
Intermolecular Hydrogen Bond ◽  
X Ray Diffraction ◽  
Compound I ◽  
Hydrogen Bond Formation ◽  
Compound Ii

Objectives. The paper is devoted to the crystal structure characterization of 5-methyl-2-phenyl4H-pyrazol-3-one (compound I) and 2-(4-chlorophenyl)-5-methyl-4H-pyrazol-3-one (compound II).Methods. Single-crystal X-ray diffraction studies and theoretical calculations: Density functional theory and quantum theory of atoms in molecules.Results. In the solid state, the crystal structure of compound I is characterized by the alternation of OH and NH tautomers connected via O–H---O and N–H---N hydrogen bonds. For compound II, the existence of chains built from the NH monomers via hydrogen bonding can be explained by the peculiarities of cooperative effects. In the framework of quantum theory of atoms in molecules, the following topological characteristics are calculated for all dimers: electron density, Laplacian of electron density, density of kinetic, potential, and total energy in the critical point of the intermolecular hydrogen bond. It is concluded that the hydrogen bond in dimers 1–4, 7 (compound I), and 8–11 (compound II) can be assigned to the intermediate (between covalent and dispersion types) interaction owing to hydrogen bond formation with the participation of electronegative oxygen- (and/or nitrogen-) atoms, whereas H-bond in dimers 5 and 6 (compound I) can be attributed to the dispersion one (no hydrogen bond formation or weak H-bond formation), and it represents the weak interaction, being in agreement with length for intermolecular hydrogen bond in dimers. The electron density and total energy density values demonstrate that the strongest intermolecular H-bonds take place in dimers 1 (OH---O), 4 (OH---O), 7 (OH---N), 8 (OH---O), 9 (NH---N), and 11 (OH---N). The results obtained for compounds I and II are compared with data for antipyrine (1,2-dihydro-1,5-dimethyl-2-phenyl-3H-pyrazol-3-one; compound III)Conclusions. An important role of intermolecular hydrogen bonding in the crystal packing, molecule association and self-organization via dimer- or more extended species formation has been demonstrated. 

scholarly journals The crystal structures of three clozapinium salts: different molecular configurations, and supramolecular assembly in one, two and three dimensions

2015 ◽  
Vol 71 (4) ◽  
pp. 406-413 ◽  
Author(s):  
Manpreet Kaur ◽  
Jerry P. Jasinski ◽  
Hemmige S. Yathirajan ◽  
Channappa N. Kavitha ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Dimethyl Sulfoxide ◽  
Three Dimensional ◽  
Supramolecular Assembly ◽  
Three Dimensions ◽  
Planar Geometry ◽  
Compound I ◽  
Protonation Site ◽  
Piperazine Ring ◽  
Compound Ii

The structures of three salts derived from clozapine, 8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine, are reported, namely, clozapinium 3,5-dinitrobenzoate dimethyl sulfoxide monosolvate, C18H20ClN4+·C7H3N2O6−·C2H6OS, (I), where the dimethyl sulfoxide component is disordered over two sets of atomic sites having occupancies 0.627 (2) and 0.373 (2); clozapinium hydrogen maleate 0.21-hydrate, C18H20ClN4+·C4H3O4−·0.21H2O, (II), and clozapinium 2-hydroxybenzoate, C18H20ClN4+·C7H5O3−, (III). In all three salts, the protonation site is the methylated N atom of the piperazine ring, and the dimensions and conformations of the fused tricyclic system are very similar. However, differences are apparent in the piperazine component: in both compounds (II) and (III), the unprotonated N atom of this ring has a pyramidal geometry, but in compound (I) this atom has a planar geometry. In compound (III), both N-substituents in this ring occupy equatorial sites, but in compound (II) the fused tricyclic system occupies an axial site of the piperazine ring. The independent components of compound (I) are linked within the selected asymmetric unit by a combination of N—H...O and C—H...O hydrogen bonds, and these hydrogen-bonded aggregates are linked into chains by an aromatic π–π stacking interaction. In compound (II), the components are linked into sheets by a combination of O—H...O, N—H...O and C—H...O hydrogen bonds, and in compound (III), a combination of N—H...O, C—H...O and C—H...N hydrogen bonds links the components into a three-dimensional framework structure. Comparisons are made with some similar compounds.

N-[2-(Aminocarbonyl)phenyl]-4-hydroxy-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide dimethyl sulfoxide solvate

2007 ◽  
Vol 63 (11) ◽  
pp. o4215-o4216 ◽  
Author(s):  
Muhammad Zia-ur-Rehman ◽  
Jamil Anwar Choudary ◽  
Mark R. J. Elsegood ◽  
Hamid Latif Siddiqui ◽  
George W. Weaver
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Dimethyl Sulfoxide ◽  
Title Compound ◽  
Dmso Molecule ◽  
Biologically Active ◽  
Intermolecular Hydrogen Bonds ◽  
Compound C ◽  
Hydrogen Bonded

The title compound, C16H13N3O5S·C2H6OS, is of interest as a precursor to biologically active (benzothiazin-3-yl)quinazolinones and its structure is reported here as the dimethyl sulfoxide (DMSO) solvate. The structure displays intramolecular N—H...O and O—H...O hydrogen bonding, giving rise to six-membered hydrogen-bonded rings, with head-to-tail intermolecular pairs of N—H...O hydrogen bonds linking pairs of neighbouring molecules and two independent N—H...O=S intermolecular hydrogen bonds to the DMSO molecule resulting in the pairs of molecules being linked into stepped chains parallel to a.

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