Polysulfonylamine, CLXXXIX [1]. Weitere Beispiele für die O-Protonierung von Harnstoffen mit Di(organosulfonyl)aminen: Bildung und Kristallstrukturen von 1,1-Dimethyluroniumdi( 4-fluorbenzolsulfonyl)amid und Di(1-methylharnstoff)- hydrogen(I)-di(4-fluorbenzolsulfonyl)amid/ Polysulfonylamines, CLXXXIX. Additional Examples of the O-Protonation of Ureas by Di(organosulfonyl)amines: Formation and Crystal Structures of 1,1-Dimethyluronium Di(4-fluorobenzenesulfonyl)amide and Di(1-methylurea)hydrogen(I)Di(4-fluorobenzenesulfonyl) amide

2010 ◽  
Vol 65 (11) ◽  
pp. 1363-1371 ◽  
Author(s):  
Christoph Wölper ◽  
Alejandra Rodríguez-Gimeno ◽  
Katherine Chulvi Iborra ◽  
Peter G. Jones ◽  
Armand Blaschette
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Proton Transfer ◽  
Petroleum Ether ◽  
Crystal Structures ◽  
Monoclinic Space Group ◽  
One Dimensional ◽  
Bond Lengths ◽  
Ionic Compounds ◽  
Specific Elongation

Co-crystallization of N-methyl-substituted ureas with di(organosulfonyl)amines, (RSO2)2NH, leads unpredictably to either molecular co-crystals or, via proton transfer, to uronium salts. As a sequel to former reports, this communication describes the formation and the crystal structures of the new ionic compounds 1,1-dimethyluronium di(4-fluorobenzenesulfonyl)amide (1, monoclinic, space group P21/c, Z´ = 1) and di(1-methylurea)hydrogen(I) di(4-fluorobenzenesulfonyl)amide (2, triclinic, P1̄, Z´ = 1); both salts were obtained from dichloromethane/petroleum ether. In the structure of 2, the urea moieties of the cationic homoconjugate are connected by a very short [O-H· · ·O]+ hydrogen bond [d(O· · ·O) = 244.6(2) pm, θ (O-H· · ·O)≈170°, bridging H atom asymmetrically disordered over two positions]. The O-protonation induces a specific elongation of the C-O bond lengths to 131.2(2) pm in 1 or 129.5(2) and 127.4(2) pm in 2, as compared to literature data of ca. 126 pm for the unprotonated ureas. Both crystal structures are dominated by conventional two- and threecentre hydrogen bonds, which involve the OH and all NH donors and give rise to one-dimensional cation-anion arrays. In particular, the ionic entities of 1 are alternatingly associated into simple chains propagated by glide-plane operations parallel to the c axis, whereas the donor-richer structure of 2 displays inversion symmetric dimers of formula units, which are further hydrogen-bonded into strands propagated by translation parallel to the a axis.

Aminkomplexe von Silber(I)-disulfonylamiden, Teil I: Sekund¨are Amine [1]

2011 ◽  
Vol 66 (5) ◽  
pp. 449-458
Author(s):  
Eva-Maria Zerbe ◽  
Christoph Wölper ◽  
Peter G. Jones
Keyword(s):  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Secondary Amine ◽  
Linear Arrays ◽  
Bond Angles ◽  
Bond Lengths ◽  
Ionic Compounds ◽  
State 1 ◽  
Molecular Compounds

We report the crystal structures of five amine-complexed silver(I) disulfonylamides of composition L2AgX (L = secondary amine, X = disulfonylamide anion) [1: bis(2,2,6,6-tetramethylpiperidine)- silver(I) dimesylamide, 2: bis(2,2,6,6-tetramethylpiperidine)(1,1,3,3-tetraoxo-1,3,2-benzodithiazolido) silver(I), 3: bis(diethylamine)(dimesylamido)silver(I), 4: bis(diethylamine)silver(I) 1,1,3,3-tetraoxo- 1,3,2-benzodithiazolide, 5: bis(dicyclohexylamine)silver(I) 1,1,3,3-tetraoxo-1,3,2-benzodithiazolide]. In the solid state 1, 4 and 5 are ionic compounds, whereas 2 and 3 appear to be molecular, but with long Ag-Ndisulfonylamide bonds (ca. 2.5 Å ), almost linear Namine-Ag-Namine bond angles (171, 158°) and S-N bond lengths more typical of purely ionic disulfonylamides. The packing of these complexes is governed by the formation of chains via motifs of Ag・ ・ ・O contacts and classical hydrogen bonds. The interaction motifs vary slightly depending on the steric demand of the amine substituents. For the molecular compounds, either new motifs appear (3) or intramolecular classical hydrogen bonds are formed, and linear arrays of molecules are generated by non-classical hydrogen bonds (2)

Zur Kristallchemie von Supersäuren: Bildung und Struktur der tiefschmelzenden Addukte SbF5 · CF3SO3H und SbF5 · 7 HF [1] / Crystal Chemistry of Superacids: Formation and Structure of the Low-Melting Adducts SbF5 · CF3SO3H and SbF5 · 7 HF [1]

1991 ◽  
Vol 46 (12) ◽  
pp. 1659-1663 ◽  
Author(s):  
Dietrich Mootz ◽  
Klemens Bartmann
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Chemistry ◽  
Unit Cell ◽  
Monoclinic Space Group ◽  
The Novel ◽  
Melting Diagram ◽  
Complex Molecules ◽  
One Dimensional

The melting diagram of the superacid system SbF5—CF3SO3H as well as of SbF5—HF has been studied by DTA and the crystal structure of one newly found low-melting adduct in each case determined. The adduct SbF5 · CF3SO3H (m.p. — 1°C, monoclinic, space group P21/c, Z = 4 formula units per unit cell) is composed of complex molecules F5SbOS(CF3)(O)OH which are linked by strong hydrogen bonds O-H ···F to infinite chains. The adduct SbF5 · 7HF (melting incongruently at —75°C, monoclinic, I 2/m, Z = 2) is a fluoronium salt, (H7F6)SbF6. The novel H7F6+ cation is formed as an unbranched chain by very strong hydrogen bonds between the respective F atoms, which become weaker from the center to the ends. A further hydrogen bond of this kind, between the cations and the octahedral SbF6- anions, again leads to a one-dimensional polymer.

scholarly journals Synthesis and crystal structures of [Ph3PCH2PPh3]I2 dichloromethane disolvate and [Ph3PCH2PPh3](BI4)2

2017 ◽  
Vol 73 (8) ◽  
pp. 1259-1263 ◽  
Author(s):  
Rakesh Ganguly ◽  
Violeta Jevtovic
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Bond Lengths ◽  
Solvent Molecules

Reaction of BI3 with carbodiphosphorane, C(PPh3)2, gives a mixture of the dicationic compounds, methylenebis(triphenylphosphonium) diiodide dichloromethane disolvate, C37H32P2 2+·2I−·2CH2Cl2 or [Ph3PCH2PPh3]I2·2CH2Cl2 (I), methylenebis(triphenylphosphonium) bis(tetraiodoborate), C37H32P2 2+·2BI4 − or [Ph3PCH2PPh3](BI4)2 (II). Solvents are the source of the protons at the ylidic C atom. The P—C—P angle is 124.1 (2)° for (I) and 121.7 (3)° for (II), while the two P—C bond lengths are 1.804 (4) and 1.807 (5) Å in (I), and 1.817 (5) and 1.829 (5) Å in (II). In the crystal of (I), the protons of the central P—CH2—P C atom exhibit weak C—H...I hydrogen bonds with the respective anions. The anions in turn are linked to the dichloromethane solvent molecules by C—H...I hydrogen bonds. In the crystal of (II), one of the BI4 − anions is linked to a phenyl H atom via a weak C—H...I hydrogen bond.

Polysulfonylamine, CXCII [1]. Polynäre Verbindungen aus Di(4-fluorbenzolsulfonyl) amin (FAH), 1,1,3-Trimethylharnstoff (TrMU) und Dimethylamin (Me2NH): Bildung und Strukturen des Cokristalls FAH·TrMU (Z′ = 1), des Salzes Me2NH2 +·FA– (Z′ = 6) und des Salz-Cokristalls FAH·TrMU·Me2NH2 +·FA– (Z′ = 1). Bemerkungen zur Oxophobie von C–F-Gruppen in Kristallstrukturen / Polysulfonylamines, CXCII. Polynary Compounds Based upon Di(4-fluorobenzenesulfonyl)amine (FAH), 1,1,3-Trimethylurea (TrMU) and Dimethylamine (Me2NH): Formation and Structures of the Cocrystal FAH·TrMU (Z′ = 1), the Salt Me2 NH2 +·FA− (Z′ = 6) and the Salt Cocrystal FAH·TrMU·Me2NH2 +·FA− (Z′ = 1). Comments on the Oxophobia of C–F Groups in Crystal Structures

2011 ◽  
Vol 66 (11) ◽  
pp. 1161-1174
Author(s):  
Christoph Wölper ◽  
Alejandra Rodríguez-Gimeno ◽  
Katherine Chulvi Iborra ◽  
Ina Dix ◽  
Matthias Freytag ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Petroleum Ether ◽  
Crystal Structures ◽  
Hydrolysis Reaction ◽  
Formula Unit ◽  
Halogen Bonds ◽  
Ionic Polymer ◽  
One Dimensional ◽  
Independent Unit ◽  
Salt Component

Cocrystallization of di(4-fluorobenzenesulfonyl)amine, (4-F-C6H4SO2)2NH (= FAH), with 1,3,3- trimethylurea (TrMU) from dichloromethane/petroleum ether afforded the molecular cocrystal FAH・TrMU (1, monoclinic, P21/n, Z′ = 1) and the salt cocrystal FAH・TrMU・Me2NH2+・FA− (2, monoclinic, P21, Z′ = 1). The minor product 2 resulted from a hydrolysis reaction of TrMU and was obtained by serendipity. The salt component of 2, Me2NH2+・FA− (3, monoclinic, C2, Z′ = 6), was prepared by metathesis of [Me2NH2]Cl with Ag[FA] and is not isomorphous to its previously reported congeners Me2NH2+・(4-X-C6H4SO2)2N− (4 - 7 for X = Cl, Br, I or Me, all monoclinic, Cc, Z′ = 1). The three new structures display one-dimensional arrays (catemers) based upon classical two- or three-centre hydrogen bonds that use N-H or N+-H groups as donors and S=O, C=O or N− groups as acceptors. In 1, the catemers consist of alternating FAH and TrMU molecules, in 3 of alternating Me2NH2+ and FA− ions (six independent formula units), in 2 of alternating Me2NH2+ and FA− ions (one independent unit) and FAH・ ・ ・ TrMU・ ・ ・ heterodimers acting as side-groups to the ionic polymer. The packings of 1 - 3 are completely devoid of short fluorine-oxygen contacts below the van derWaals limit, as are all the known crystal structures containing FAH or FA− entities (“oxophobia” of the C-F groups). The Z′ = 6 structure of 3 may be interpreted as a stratagem to avoid short F・ ・ ・O contacts, in contrast to the Z′ = 1 structures of 4 - 6, which exhibit hydrogen-bonded ion catemers similar to the catemer of 3, and two halogen bonds C-X・ ・ ・O=S per formula unit

Cyclic heterotetrameric and low-dimensional hydrogen-bonded polymeric structures in the morpholinium salts of ring-substituted benzoic acid analogues

2016 ◽  
Vol 72 (2) ◽  
pp. 105-111 ◽  
Author(s):  
Graham Smith ◽  
Daniel E. Lynch
Keyword(s):  
Hydrogen Bond ◽  
Secondary Structure ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Ion Pairs ◽  
Chain Structure ◽  
Organic Salt ◽  
Structure Generation ◽  
One Dimensional ◽  
Hydrogen Bonded

The morpholinium (tetrahydro-2H-1,4-oxazin-4-ium) cation has been used as a counter-ion in both inorganic and organic salt formation and particularly in metal complex stabilization. To examine the influence of interactive substituent groups in the aromatic rings of benzoic acids upon secondary structure generation, the anhydrous salts of morpholine with salicylic acid, C4H10NO+·C7H5O3−, (I), 3,5-dinitrosalicylic acid, C4H10NO+·C7H3N2O7−, (II), 3,5-dinitrobenzoic acid, C4H10NO+·C7H3N2O6−, (III), and 4-nitroanthranilic acid, C4H10NO+·C7H5N2O4−, (IV), have been prepared and their hydrogen-bonded crystal structures are described. In the crystal structures of (I), (III) and (IV), the cations and anions are linked by moderately strong N—H...Ocarboxylhydrogen bonds, but the secondary structure propagation differs among the three,viz.one-dimensional chains extending along [010] in (I), a discrete cyclic heterotetramer in (III), and in (IV), a heterotetramer with amine N—H...O hydrogen-bond extensions alongb, giving a two-layered ribbon structure. With the heterotetramers in both (III) and (IV), the ion pairs are linked though inversion-related N—H...Ocarboxylatehydrogen bonds, giving cyclicR44(12) motifs. With (II), in which the anion is a phenolate rather than a carboxylate, the stronger assocation is through a symmetric lateral three-centre cyclicR12(6) N—H...(O,O′) hydrogen-bonding linkage involving the phenolate and nitro O-atom acceptors of the anion, with extension through a weaker O—H...Ocarboxylhydrogen bond. This results in a one-dimensional chain structure extending along [100]. In the structures of two of the salts [i.e.(II) and (IV)], there are also π–π ring interactions, with ring-centroid separations of 3.5516 (9) and 3.7700 (9) Å in (II), and 3.7340 (9) Å in (IV).

Polysulfonylamine, CXII. Neues aus der Festkörperchemie der 2-Pyridone: Isolierung und Röntgenstrukturen von Bis(2-pyridon)hydrogen(I)- und Bis(6-methyl-2-pyridon)hydrogen(I)-dimesylamid / Polysulfonylamines, CXII. A Novel Solid-State Aspect of 2-Pyridones: Isolation and X-Ray Structures of Bis(2-pyridone)hydrogen(I) and Bis(6-methyl-2-pyridone)hydrogen(I) Dimesylamides

1999 ◽  
Vol 54 (5) ◽  
pp. 643-648 ◽  
Author(s):  
Karna Wijaya ◽  
Oliver Moers ◽  
Armand Blaschette ◽  
Peter G. Jones
Keyword(s):  
Hydrogen Bond ◽  
Solid State ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Monoclinic Space Group ◽  
Space Group ◽  
X Ray ◽  
Crystal Packings

The compounds (2-pyridone)2H+(MeSO2)2N- (1, monoclinic, space group P21/n ) and (6- methyl-2-pyridone)2H+(MeSO2)2N- (2, triclinic, P1) crystallize selectively and in good yields when the parent 2-pyridones (2-hydroxypyridines) are treated with the strong NH acid dimesylamine in acetonitrile or acetone. The corresponding 2-hydroxypyridinium salts could not be obtained. In the unprecedented crystal structures of 1 and 2, two pyridone units are linked by a proton to form very short and approximately symmetric O⋯H+ ⋯O hydrogen bonds, the adjacent C-O distances being appreciably elongated as compared to “free” pyridones [1: O ⋯ O 241.8(2), C -O 127.8(3) and 129.1(2) pm; 2: O ⋯ O 243.8(2), C -O 128.1(2) and 129.2(2) pm]. In both crystal packings, the homoconjugate cations and the dimesylamide anions are alternately associated into chains by an N - H ⋯ N “ and an N - H ⋯ O hydrogen bond.

scholarly journals Crystal structures of bis[2-(pyridin-2-yl)phenyl-κ2N,C1]rhodium(III) complexes containing an acetonitrile or monodentate thyminate(1−) ligand

2016 ◽  
Vol 72 (4) ◽  
pp. 543-547
Author(s):  
Mika Sakate ◽  
Haruka Hosoda ◽  
Takayoshi Suzuki
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Octahedral Coordination ◽  
Bond Lengths

The crystal structures of bis[2-(pyridin-2-yl)phenyl]rhodium(III) complexes with the metal in an octahedral coordination containing chloride and acetonitrile ligands, namely (OC-6-42)-acetonitrilechloridobis[2-(pyridin-2-yl)phenyl-κ2N,C1]rhodium(III), [RhCl(C11H8N)2(CH3CN)] (1), thyminate(1−) and methanol, namely (OC-6-42)-methanol(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ido-κN1)bis[2-(pyridin-2-yl)phenyl-κ2N,C1]rhodium(III), [Rh(C11H8N)2(C5H5N2O2)(CH3OH)]·CH3OH·0.5H2O (2), and thyminate(1−) and ethanol, namely (OC-6-42)-ethanol(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-ido-κN1)bis[2-(pyridin-2-yl)phenyl-κ2N,C1]rhodium(III), [Rh(C11H8N)2(C5H5N2O2)(C2H5OH)]·C2H5OH (3), are reported. The acetonitrile complex,1, is isostructural with the IrIIIanalog. In complexes2and3, the monodeprotonated thyminate (Hthym−) ligand coordinates to the RhIIIatom through the N atom, and the resulting Rh—N(Hthym) bond lengths are relatively long [2.261 (2) and 2.252 (2) Å for2and3, respectively] as compared to the Rh—N bonds in the related thyminate complexes. In each of the crystals of2and3, the complexes are linkedviaa pair of intermolecular N—H...O hydrogen bonds between neighbouring Hthym−ligands, forming an inversion dimer. A strong intramolecular O—H...O hydrogen bond between the thyminate(1−) and alcohol ligands in mutuallycispositions to each other is also observed.

scholarly journals Crystal structures of butyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate

2019 ◽  
Vol 75 (6) ◽  
pp. 880-887 ◽  
Author(s):  
Rosita Diana ◽  
Angela Tuzi ◽  
Barbara Panunzi ◽  
Antonio Carella ◽  
Ugo Caruso
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Molecular Structures ◽  
Antitumoral Activity ◽  
Space Group ◽  
One Dimensional ◽  
Axis Direction ◽  
Hydrogen Bonding Pattern ◽  
Butyl Group

The title benzofuran derivatives 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF1), C19H18N2O6, and 2-methoxyethyl 2-amino-5-hydroxy-4-(4-nitrophenyl)benzofuran-3-carboxylate (BF2), C18H16N2O7, recently attracted attention because of their promising antitumoral activity. BF1 crystallizes in the space group P\overline{1}. BF2 in the space group P21/c. The nitrophenyl group is inclined to benzofuran moiety with a dihedral angle between their mean planes of 69.2 (2)° in BF1 and 60.20 (6)° in BF2. A common feature in the molecular structures of BF1 and BF2 is the intramolecular N—H...Ocarbonyl hydrogen bond. In the crystal of BF1, the molecules are linked head-to-tail into a one-dimensional hydrogen-bonding pattern along the a-axis direction. In BF2, pairs of head-to-tail hydrogen-bonded chains of molecules along the b-axis direction are linked by O—H...Omethoxy hydrogen bonds. In BF1, the butyl group is disordered over two orientations with occupancies of 0.557 (13) and 0.443 (13).

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.

(1R*,5R*,7R*,8S*)-3-(3,4-Dihydroxybenzoyl)-4-hydroxy-8-methyl-1,5,7-tris(3-methyl-2-butenyl)-8-(4-methyl-3-pentenyl)bicyclo[3.3.1]non-3-ene-2,9-dione

2007 ◽  
Vol 63 (3) ◽  
pp. o1282-o1284 ◽  
Author(s):  
Bruno Ndjakou Lenta ◽  
Diderot Tchamo Noungoue ◽  
Krishna Prasad Devkota ◽  
Patrice Aime Fokou ◽  
Silvere Ngouela ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Medicinal Plant ◽  
Chair Conformation ◽  
The Other ◽  
Aryl Group ◽  
One Dimensional ◽  
Compound C ◽  
Bicyclic System ◽  
Symphonia Globulifera

The title compound, C38H50O6, also known as guttiferone A, was isolated from the medicinal plant Symphonia globulifera. It is a benzophenone derivative where one aryl group is derivatized to give a bicyclic system which has two prenyl groups attached to the bridgehead. One of the cyclohexane rings in the bicyclic system is in a chair form, while the other has a distorted half-chair conformation. In addition to an intramolecular O—H...O hydrogen bond, intermolecular O—H...O hydrogen bonds link molecules into one-dimensional chains.

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