scholarly journals Three closely related dibenzazepine carboxylic acids: hydrogen-bonded aggregation in one, two and three dimensions

2014 ◽  
Vol 70 (3) ◽  
pp. 332-337 ◽  
Author(s):  
Carlos M. Sanabría ◽  
Alirio Palma ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Carboxylic Acids ◽  
Three Dimensional ◽  
Three Dimensions ◽  
Framework Structure ◽  
Hydrogen Bonded

In the structure of (6R*,11R*)-5-acetyl-11-ethyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-carboxylic acid, C19H19NO3, (I), the molecules are linked into sheets by a combination of O—H...O and C—H...O hydrogen bonds; in the structure of the monomethyl analogue (6RS,11SR)-5-acetyl-11-ethyl-2-methyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-carboxylic acid, C20H21NO3, (II), the molecules are linked into simpleC(7) chains by O—H...O hydrogen bonds; and in the structure of the dimethyl analogue (6RS,11SR)-5-acetyl-11-ethyl-1,3-dimethyl-6,11-dihydro-5H-dibenzo[b,e]azepine-6-carboxylic acid, C21H23NO3, (III), a combination of O—H...O, C—H...O and C—H...π(arene) hydrogen bonds links the molecules into a three-dimensional framework structure. None of these structures exhibits theR22(8) dimer motif characteristic of simple carboxylic acids.

Adducts of 1,4,8,11-tetraazacyclotetradecane with carboxylic acids: hydrogen-bonded supramolecular structures in two or three dimensions

2004 ◽  
Vol 60 (1) ◽  
pp. 65-75 ◽  
Author(s):  
Choudhury M. Zakaria ◽  
Alan J. Lough ◽  
George Ferguson ◽  
Christopher Glidewell
Keyword(s):  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Water Molecule ◽  
Carboxylic Acids ◽  
Rotation Axis ◽  
Three Dimensional ◽  
Supramolecular Structures ◽  
Three Dimensions ◽  
Water Molecules ◽  
Two Dimensional

Four solvated salt-type adducts derived from cyclam (1,4,8,11-tetraazacyclotetradecane) and carboxylic acids have been structurally characterized. In the salt derived from adamantane-1-carboxylic acid, 4,11-diaza-1,8-diazoniacyclotetradecane bis(adamantane-1-carboxylate) tetrahydrate, (1) (monoclinic, P21/c, Z′ = 0.5), where the cation lies across a centre of inversion, the anions and the water molecules form chains of edge-fused R_4^2(8) and R_6^6(16) rings, which are linked into sheets by the cations. In the 4-aminobenzoate salt, 4,11-diaza-1,8-diazoniacyclotetradecane bis(4-aminobenzoate) monohydrate, (2) (monoclinic, C2/c, Z′ = 0.5), where the cation lies across a centre of inversion and the water molecule lies across a twofold rotation axis, the cations and anions generate a three-dimensional framework, readily analysed in terms of two distinct two-dimensional substructures, viz. (10\overline 1) sheets of R_8^6(46) rings, and pairwise interwoven (100) sheets, reinforced by water molecules. The 3-hydroxybenzoate salt, 4,11-diaza-1,8-diazoniacyclotetradecane bis(3-hydroxybenzoate) dihydrate, (3) (monoclinic, Pc, Z′ = 1), contains a three-dimensional framework constructed from anions and water molecules only, which encapsulates large voids and within which the cations are linked to the anion–water framework via N—H...O hydrogen bonds. There are two independent cations in 4,11-diaza-1,8-diazoniacyclotetradecane 5-hydroxyisophthalate(2−) methanol solvate, (4) (monoclinic, P21/c, Z′ = 1), both lying across centres of inversion but with entirely different configurations. The anions alone form simple chains, and these chains are linked by the two types of cation into a three-dimensional framework from which the methanol molecules are pendent. Comparisons are made with carboxylate complexes of the [Ni(cyclam)]2+ cation and with carboxylate salts derived from meso-5,5,7,12,12,14-hexamethyl-1,4,8,11-tetraazacyclotetradecane.

N 6-Substituted 2-amino-4-chloro-5-formylpyrimidines: puckered versus planar pyrimidine rings, and hydrogen-bonded aggregation in zero, one, two and three dimensions

2008 ◽  
Vol 64 (5) ◽  
pp. 596-609 ◽  
Author(s):  
Justo Cobo ◽  
Jorge Trilleras ◽  
Jairo Quiroga ◽  
Antonio Marchal ◽  
Manuel Nogueras ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Electronic Structures ◽  
Negative Charge ◽  
Positive Charge ◽  
Three Dimensional ◽  
Three Dimensions ◽  
Framework Structure ◽  
Molecular Electronic ◽  
Twist Boat ◽  
Hydrogen Bonded

The structures of 12 new N 6-substituted 2-amino-4-chloro-5-formylpyrimidines, where the N 6 substituent is of the type NHR or NR 1 R 2, have been determined. The intramolecular dimensions provide strong evidence for the development of polarized, charge-separated molecular-electronic structures, with the positive charge delocalized over the two exocyclic amino N atoms and with negative charge on the formyl O atom. This polarization appears to be independent of the significant puckering, in seven of the compounds, of the pyrimidine rings from planarity towards boat, twist-boat or screw-boat conformations. In 11 of the compounds studied here, N—H...N hydrogen bonds link pairs of molecules into centrosymmetric R_2^2(8) dimer units, and their overall crystal structures are determined by the patterns of hydrogen bonds by which these units are further linked. Examples are reported in which no further hydrogen bonding occurs; in which the R_2^2(8) dimers are linked into chains of rings, or into sheets; and in which sheets are formed by the π-stacking of hydrogen-bonded chains of rings. In the sole structure lacking the R_2^2(8) dimer motif, N—H...O and N—H...N hydrogen bonds cooperate to generate a three-dimensional framework structure.

scholarly journals Three isomeric 1-(2-chloronicotinoyl)-2-(nitrophenyl)hydrazines, including three polymorphs of 1-(2-chloronicotinoyl)-2-(2-nitrophenyl)hydrazine: hydrogen-bonded supramolecular structures in two and three dimensions

2007 ◽  
Vol 63 (1) ◽  
pp. 101-110 ◽  
Author(s):  
Solange M. S. V. Wardell ◽  
Marcus V. N. de Souza ◽  
James L. Wardell ◽  
John N. Low ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Three Dimensions ◽  
Framework Structure ◽  
Stacking Interaction ◽  
Space Groups ◽  
Isomeric Compound ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Polymorphic Forms

1-(2-Chloronicotinoyl)-2-(2-nitrophenyl)hydrazine, C12H9ClN4O3, crystallizes in three polymorphic forms, two monoclinic forms in space groups Cc (Ia) and P21 (Ib), and an orthorhombic form in space group Pbcn (Ic). In the Cc polymorph (Ia) the molecules are linked into sheets by combinations of one N—H...O and two C—H...O hydrogen bonds, while in the P21 polymorph (Ib) the molecules are linked into sheets by combinations of three hydrogen bonds, one each of N—H...O, C—H...N and C—H...O types. In the orthorhombic polymorph (Ic) the molecules are linked into a complex three-dimensional framework structure by a combination of one N—H...O, one N—H...N and three C—H...O hydrogen bonds, and an aromatic π...π stacking interaction. In the isomeric compound 1-(2-chloronicotinoyl)-2-(3-nitrophenyl)hydrazine (II) the molecules are again linked into a three-dimensional framework, this time by a combination of three hydrogen bonds, one each of N—H...O, N—H...N and C—H...O types, weakly augmented by a π...π stacking interaction. The molecules of 1-(2-chloronicotinoyl)-2-(4-nitrophenyl)hydrazine (III) are linked into sheets by a combination of three hydrogen bonds, one each of N—H...O, N—H...N and C—H...O types.

Hydrogen bonding in two ammonium salts of 5-sulfosalicylic acid: ammonium 3-carboxy-4-hydroxybenzenesulfonate monohydrate and triammonium 3-carboxy-4-hydroxybenzenesulfonate 3-carboxylato-4-hydroxybenzenesulfonate

2013 ◽  
Vol 69 (5) ◽  
pp. 534-537 ◽  
Author(s):  
Graham Smith ◽  
Urs D. Wermuth
Keyword(s):  
Hydrogen Bonding ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Ammonium Salts ◽  
Framework Structure ◽  
Sulfosalicylic Acid ◽  
Crystalline Materials ◽  
Rotation Axes ◽  
Ammonium N

The structures of two ammonium salts of 3-carboxy-4-hydroxybenzenesulfonic acid (5-sulfosalicylic acid, 5-SSA) have been determined at 200 K. In the 1:1 hydrated salt, ammonium 3-carboxy-4-hydroxybenzenesulfonate monohydrate, NH4+·C7H5O6S−·H2O, (I), the 5-SSA−monoanions give two types of head-to-tail laterally linked cyclic hydrogen-bonding associations, both with graph-setR44(20). The first involves both carboxylic acid O—H...Owaterand water O—H...Osulfonatehydrogen bonds at one end, and ammonium N—H...Osulfonateand N—H...Ocarboxyhydrogen bonds at the other. The second association is centrosymmetric, with end linkages through water O—H...Osulfonatehydrogen bonds. These conjoined units form stacks downcand are extended into a three-dimensional framework structure through N—H...O and water O—H...O hydrogen bonds to sulfonate O-atom acceptors. Anhydrous triammonium 3-carboxy-4-hydroxybenzenesulfonate 3-carboxylato-4-hydroxybenzenesulfonate, 3NH4+·C7H4O6S2−·C7H5O6S−, (II), is unusual, having both dianionic 5-SSA2−and monoanionic 5-SSA−species. These are linked by a carboxylic acid O—H...O hydrogen bond and, together with the three ammonium cations (two on general sites and the third comprising two independent half-cations lying on crystallographic twofold rotation axes), give a pseudo-centrosymmetric asymmetric unit. Cation–anion hydrogen bonding within this layered unit involves a cyclicR33(8) association which, together with extensive peripheral N—H...O hydrogen bonding involving both sulfonate and carboxy/carboxylate acceptors, gives a three-dimensional framework structure. This work further demonstrates the utility of the 5-SSA−monoanion for the generation of stable hydrogen-bonded crystalline materials, and provides the structure of a dianionic 5-SSA2−species of which there are only a few examples in the crystallographic literature.

Two closely related, and unexpected, quinolinone derivatives: a three-dimensional hydrogen-bonded framework structure and a hydrogen-bonded molecular ribbon ofR22(18) andR44(24) rings

2012 ◽  
Vol 68 (6) ◽  
pp. o220-o225
Author(s):  
Daniel Insuasty ◽  
Rodrigo Abonía ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Unit Cell ◽  
Isomeric Form ◽  
Framework Structure ◽  
Space Group ◽  
Solvent Molecules ◽  
Hydrogen Bonded

1,5-Bis(4-chlorophenyl)-3-(2-oxo-1,2-dihydroquinolin-3-yl)pentane-1,5-dione, (Ia), and 1,5-bis(2-chlorophenyl)-3-(2-oxo-1,2-dihydroquinolin-3-yl)pentane-1,5-dione, (Ib), crystallize as an 84:16 mixture, 0.84C26H19Cl2NO3·0.16C26H19Cl2NO3, in the space groupI41/a, where the molecules of the two isomers occupy very similar sites in the unit cell. A combination of one N—H...O hydrogen bond and one C—H...O hydrogen bond links the molecules, regardless of isomeric form, into a single three-dimensional framework structure. The molecules of (9RS,10RS)-8,9-bis(4-chlorobenzyl)-10-(2-oxo-1,2-dihydroquinolin-3-yl)-5,6,9,10-tetrahydrophenanthridine, C36H22Cl2N2O4, (II), are linked by two hydrogen bonds, one each of the N—H...O and C—H...O types, into a molecular ribbon in which centrosymmetric rings ofR22(18) andR44(24) types alternate. The hydrogen-bonded ribbons enclose channels, which contain highly disordered solvent molecules.

Three closely related thienyl-substituted 1,4-epoxynaphtho[1,2-b]azepines: hydrogen-bonded assembly in one, two and three dimensions

2013 ◽  
Vol 69 (3) ◽  
pp. 307-312 ◽  
Author(s):  
Andrés F. Yépes ◽  
Alirio Palma ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Geometrical Isomer ◽  
Three Dimensions ◽  
Racemic Mixtures ◽  
Hydrogen Bonded

(2R,4S)-2-(3-Methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C19H17NOS, (I), crystallizes with a single enantiomer in each crystal, whereas its geometrical isomer (2RS,4SR)-2-(5-methylthiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxy-naphtho[1,2-b]azepine, (II), and (2RS,4SR)-2-(5-bromothiophen-2-yl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine, C18H14BrNOS, (III), both crystallize as racemic mixtures. A combination of one C—H...O hydrogen bond and two C—H...π(arene) hydrogen bonds links the molecules of (I) into a three-dimensional framework; the molecules of (II) are linked into aC(4)C(4)[R22(7)] chain of rings by a combination of C—H...N and C—H...O hydrogen bonds; and in (III), whereZ′ = 2, a combination of four C—H...π(arene) hydrogen bonds and two C—H...π(thienyl) hydrogen bonds links the molecules into complex sheets. Comparisons are made with the assembly patterns in some aryl-substituted 1,4-epoxynaphtho[1,2-b]azepines.

(Z)-5-[(5-Methyl-1H-imidazol-4-yl)methylidene]-2-sulfanylidene-1,3-thiazolidin-4-one monohydrate: a three-dimensional hydrogen-bonded framework structure

2012 ◽  
Vol 68 (11) ◽  
pp. o468-o471 ◽  
Author(s):  
Alberto Insuasty ◽  
Braulio Insuasty ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Title Compound ◽  
Three Dimensional ◽  
Organic Component ◽  
Framework Structure ◽  
Compound C ◽  
Molecular Components ◽  
Hydrogen Bonded

The non-H atoms in the organic component of the title compound, C8H7N3OS2·H2O, are almost coplanar, as the dihedral angle between the two ring planes is only 1.8 (2)°; there is a wide C—C—C angle of 127.8 (3)° at the methine C atom linking the two rings. The molecular components are linked into a three-dimensional framework structure by two-centre hydrogen bonds of N—H...O and O—H...N types, together with a three-centre O—H...(N,S) system. Comparisons are made with some (Z)-5-arylmethylidene-2-sulfanylidene-1,3-thiazolidin-4-ones.

scholarly journals Tris(2,2′-bipyridine)iron(II) bis(1,1,3,3-tetracyano-2-ethoxypropenide) dihydrate: chiral hydrogen-bonded frameworks interpenetrate in three dimensions

2014 ◽  
Vol 70 (5) ◽  
pp. 465-469 ◽  
Author(s):  
Zouaoui Setifi ◽  
Fatima Setifi ◽  
Habib Boughzala ◽  
Adel Beghidja ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Three Dimensions ◽  
Water Molecules ◽  
Space Group ◽  
Rotation Axes ◽  
Hydrogen Bonded

In the title compound, [Fe(C10H8N2)3](C9H5N4O)2·2H2O, the chiral cations lie across twofold rotation axes in the space group C2/c. The anions and the water molecules are linked by two independent O—H...N hydrogen bonds to form C 2 2(8) chains, and these chains are linked by the cations via C—H...N and C—H...O hydrogen bonds to form two interpenetrating three-dimensional frameworks, each of which contains only one enantiomeric form of the chiral cation.

Salts of 3,5-dinitrobenzoic acid with organic diamines: hydrogen-bonded supramolecular structures in one, two and three dimensions

2001 ◽  
Vol 57 (2) ◽  
pp. 201-212 ◽  
Author(s):  
Colin J. Burchell ◽  
Christopher Glidewell ◽  
Alan J. Lough ◽  
George Ferguson
Keyword(s):  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Secondary Amine ◽  
Tertiary Amine ◽  
Primary Amine ◽  
Three Dimensional ◽  
Supramolecular Structures ◽  
Three Dimensions ◽  
Two Dimensional ◽  
One Dimensional

The trigonally trisubstituted carboxylic acid 3,5-dinitrobenzoic acid, (O2N)2C6H3COOH, forms 2:1 salts with a range of organic diamines L, with the general composition [LH2]2+·[{(O2N)2C6H3COO}−]2. When L is a bis-tertiary amine the hard N—H...O hydrogen bonds generate finite three-component aggregates, anion...cation...anion, and these aggregates are further linked by soft C—H...O hydrogen bonds to form one-dimensional molecular ladders when L is N,N,N′,N′′-tetramethyl-1,2-diaminoethane and chains of rings when L is 4,4′-dipyridylethane or 4,4′-dipyridylethene; two-dimensional sheets are formed when L is 1,4-diazabicyclo[2.2.2]octane and a three-dimensional framework is formed when L is N,N′-dimethylpiperazine. When L is the bis-secondary amine piperazine, the hard N—H...O and soft C—H...O hydrogen bonds each generate continuous motifs in the form of distinct chains of rings, the combination of which generates sheets, while when L is the bis-primary amine 1,2-diaminoethane the hard N—H...O hydrogen bonds alone generate a three-dimensional framework.

scholarly journals Hydrogen-bonded adducts of triphenylsilanol with diamines: a finite ten-molecule aggregate, and chain, sheet and framework structures built from O—H...O, O—H...N and C—H...π(arene) hydrogen bonds

2004 ◽  
Vol 60 (2) ◽  
pp. 238-248 ◽  
Author(s):  
David E. Turkington ◽  
Alan J. Lough ◽  
George Ferguson ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Framework Structure ◽  
Orientational Disorder ◽  
A Chain ◽  
Molecular Components ◽  
Hydrogen Bonded

The structures of five hydrogen-bonded adducts of triphenylsilanol, Ph3SiOH, with diamines have been determined. In the 4:1 adduct formed with 1,4-diazabicyclo[2.2.2]octane, (Ph3SiOH)4·C6H12N2 (I) (triclinic, P\bar 1, Z′ = 2), there are two independent five-component aggregates built from O—H...N and O—H...O hydrogen bonds, in one of which the diamine exhibits orientational disorder: these two aggregates are linked into a cyclic ten-molecule unit by means of two independent C—H...π(arene) hydrogen bonds. The 4:1 adduct formed with 1,2-bis(4-pyridyl)ethene, (Ph3SiOH)4·C12H10N2 (II) (triclinic, P\bar 1, Z′ = 0.5), forms a similar five-component aggregate which lies across a centre of inversion: a single C—H...π(arene) hydrogen bond links these aggregates into a molecular ladder. With N,N′-dimethylpiperazine, triphenylsilanol forms a 2:1 adduct, (Ph3SiOH)2·C6H14N2 (III) (monoclinic, P21/c, Z′ = 0.5), in which a three-component aggregate built from O—H...N hydrogen bonds lies across a centre of inversion: two independent C—H...π(arene) hydrogen bonds link these aggregates into sheets. In the hydrated 2:1 adduct formed with 1,2-bis(4′-bipyridyl)ethane, (Ph3SiOH)2·C12H12N2·H2O (IV) (triclinic, P\bar 1, Z′ = 1), a combination of two independent O—H...O and two independent N—H...O hydrogen bonds links the five molecular components into a centrosymmetric eight-molecule aggregate, and six independent C—H...π(arene) hydrogen bonds link these chains into a continuous three-dimensional framework structure. In the dihydrated 2:1 adduct formed with 4,4′-bipyridyl, (Ph3SiOH)2·C10H8N2·(H2O)2 (V) (triclinic, P\bar 1, Z′ = 1), a combination of four independent O—H...O and two independent N—H...O hydrogen bonds links the five molecular components into a chain of rings, and four independent C—H...π(arene) hydrogen bonds link these chains into a continuous three-dimensional framework structure.

Sign in / Sign up

Export Citation Format

Share Document