scholarly journals Three-dimensional hydrogen-bonded framework structures in flunarizinium nicotinate and flunarizinediium bis(4-toluenesulfonate) dihydrate

2014 ◽  
Vol 70 (8) ◽  
pp. 805-811 ◽  
Author(s):  
Channappa N. Kavitha ◽  
Hemmige S. Yathirajan ◽  
Manpreet Kaur ◽  
Eric C. Hosten ◽  
Richard Betz ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Ion Pairs ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Framework Structure ◽  
Independent Components ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Ionic Components

The structures of two salts of flunarizine, namely 1-bis[(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine, C26H26F2N2, are reported. In flunarizinium nicotinate {systematic name: 4-bis[(4-fluorophenyl)methyl]-1-[(2E)-3-phenylprop-2-en-1-yl]piperazin-1-ium pyridine-3-carboxylate}, C26H27F2N2+·C6H4NO2−, (I), the two ionic components are linked by a short charge-assisted N—H...O hydrogen bond. The ion pairs are linked into a three-dimensional framework structure by three independent C—H...O hydrogen bonds, augmented by C—H...π(arene) hydrogen bonds and an aromatic π–π stacking interaction. In flunarizinediium bis(4-toluenesulfonate) dihydrate {systematic name: 1-[bis(4-fluorophenyl)methyl]-4-[(2E)-3-phenylprop-2-en-1-yl]piperazine-1,4-diium bis(4-methylbenzenesulfonate) dihydrate}, C26H28F2N22+·2C7H7O3S−·2H2O, (II), one of the anions is disordered over two sites with occupancies of 0.832 (6) and 0.168 (6). The five independent components are linked into ribbons by two independent N—H...O hydrogen bonds and four independent O—H...O hydrogen bonds, and these ribbons are linked to form a three-dimensional framework by two independent C—H...O hydrogen bonds, but C—H...π(arene) hydrogen bonds and aromatic π–π stacking interactions are absent from the structure of (II). Comparisons are made with some related structures.

scholarly journals Isomers and polymorphs of (E,E)-1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadienes

2006 ◽  
Vol 62 (4) ◽  
pp. 666-675 ◽  
Author(s):  
Christopher Glidewell ◽  
John N. Low ◽  
Janet M. S. Skakle ◽  
James L. Wardell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Space Group ◽  
Stacking Interaction ◽  
Space Groups ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Polymorphic Forms

The structures of five of the possible six isomers of (E,E)-1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadiene are reported, including two polymorphs of one of the isomers. (E,E)-1,4-Bis(2-nitrophenyl)-2,3-diaza-1,3-butadiene, C14H10N4O4 (I), crystallizes in two polymorphic forms (Ia) and (Ib) in which the molecules lie across centres of inversion in space groups P21/n and P21/c, respectively: the molecules in (Ia) and (Ib) are linked into chains by aromatic π...π stacking interactions and C—H...π(arene) hydrogen bonds, respectively. Molecules of (E,E)-1-(2-nitrophenyl)-4-(3-nitrophenyl)-2,3-diaza-1,3-butadiene (II) are linked into sheets by two independent C—H...O hydrogen bonds. The molecules of (E,E)-1,4-bis(3-nitrophenyl)-2,3-diaza-1,3-butadiene (III) lie across inversion centres in the space group P21/n, and a combination of a C—H...O hydrogen bond and a π...π stacking interaction links the molecules into sheets. A total of four independent C—H...O hydrogen bonds link the molecules of (E,E)-1-(3-nitrophenyl)-4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene (IV) into sheets. In (E,E)-1,4-bis(4-nitrophenyl)-2,3-diaza-1,3-butadiene (V) the molecules, which lie across centres of inversion in the space group P21/n, are linked by just two independent C—H...O hydrogen bonds into a three-dimensional framework.

scholarly journals Isomeric N-(iodophenyl)nitrophthalimides: interplay of C—H...O hydrogen bonds, iodo...nitro and iodo...carbonyl interactions, and aromatic π...π stacking interactions

2005 ◽  
Vol 61 (2) ◽  
pp. 227-237 ◽  
Author(s):  
Christopher Glidewell ◽  
John N. Low ◽  
Janet M. S. Skakle ◽  
Solange M. S. V. Wardell ◽  
James L. Wardell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Structures ◽  
Stacking Interactions ◽  
Stacking Interaction ◽  
Π Stacking ◽  
Π Stacking Interaction

The six isomeric N-(iodophenyl)nitrophthalimides, C14H7IN2O4, have been synthesized and the structures of five of them are reported. In N-(4-iodophenyl)-4-nitrophthalimide [(I), orthorhombic P212121] the molecules are linked into sheets by a combination of four independent C—H...O hydrogen bonds, but I...O interactions are absent. The isomers N-(3-iodophenyl)-4-nitrophthalimide [(II), monoclinic P21/c] and N-(2-iodophenyl)-4-nitrophthalimide [(III), monoclinic P21/n] both form sheets, but in (II) the molecules are linked by a combination of one two-centre iodo...nitro interaction and one C—H...O hydrogen bond into sheets containing R_4^4(30) rings, while in (III) they are linked by an iodo...carbonyl interaction and a C—H...O hydrogen bond into sheets or R_4^4(26) rings. Three-dimensional supramolecular structures are formed in both N-(4-iodophenyl)-3-nitrophthalimide [(IV), monoclinic P21/n] and N-(3-iodophenyl)-3-nitrophthalimide [(V), orthorhombic, P212121]. In (IV) the molecules are linked by a three-centre iodo...nitro interaction, three C—H...O hydrogen bonds and an aromatic π...π stacking interaction, but the framework in (V) is generated by a two-centre iodo...nitro interaction and only two C—H...O hydrogen bonds: aromatic π...π stacking interactions are absent from (V).

scholarly journals 4-Bromo-β-(2-oxoquinolin-4-yloxy)cinnamonitrile: a three-dimensional framework structure built from N—H...O and C—H...O hydrogen bonds, and bromo–carbonyl and aromatic π–π stacking interactions

2006 ◽  
Vol 62 (7) ◽  
pp. o3056-o3058 ◽  
Author(s):  
Silvia Cruz ◽  
José M. de la Torre ◽  
Justo Cobo ◽  
John N. Low ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Framework Structure ◽  
Stacking Interaction ◽  
Compound C ◽  
Π Stacking ◽  
Π Stacking Interaction

In the title compound, C18H11BrN2O2, the molecules are linked into sheets by a combination of one N—H...O and two C—H...O hydrogen bonds, and the sheets are linked by an aromatic π–π stacking interaction.

Iodo-nitroarenesulfonamides: interplay of hard and soft hydrogen bonds, I...O interactions and aromatic π...π stacking interactions

2001 ◽  
Vol 58 (1) ◽  
pp. 94-108 ◽  
Author(s):  
Craig J. Kelly ◽  
Janet M. S. Skakle ◽  
James L. Wardell ◽  
Solange M. S. V. Wardell ◽  
John N. Low ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Space Group ◽  
Rotation Axes ◽  
Π Stacking ◽  
Structural Database ◽  
A Chain

Molecules of N-(4′-iodophenylsulfonyl)-4-nitroaniline, 4-O2NC6H4NHSO2C6H4I-4′ (1), are linked by three-centre I...O2N interactions into chains and these chains are linked into a three-dimensional framework by C—H...O hydrogen bonds. In the isomeric N-(4′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4NHSO2C6H4NO2-4′ (2), the chains generated by the I...O2N interactions are again linked into a three-dimensional framework by C—H...O hydrogen bonds. Molecules of N,N-bis(3′-nitrophenylsulfonyl)-4-iodoaniline, 4-IC6H4N(SO2C6H4NO2-3′)2 (3), lie across twofold rotation axes in space group C2/c and they are linked into chains by paired I...O=S interactions: these chains are linked into sheets by a C—H...O hydrogen bond, and the sheets are linked into a three-dimensional framework by aromatic π...π stacking interactions. In N-(4′-iodophenylsulfonyl)-3-nitroaniline, 3-O2NC6H4NHSO2C6H4I-4′ (4), there are R^2_2(8) rings formed by hard N—H...O=S hydrogen bonds and R^2_2(24) rings formed by two-centre I...nitro interactions, which together generate a chain of fused rings: the combination of a C—H...O hydrogen bond and aromatic π...π stacking interactions links the chains into sheets. Molecules of N-(4′-iodophenylsulfonyl)-4-methyl-2-nitroaniline, 4-CH3-2-O2NC6H3NHSO2C6H4I-4′ (5), are linked by N—H...O=S and C—H...O(nitro) hydrogen bonds into a chain containing alternating R^2_2(8) and R^2_2(10) rings, but there are no I...O interactions of either type. There are two molecules in the asymmetric unit of N-(4′-iodophenylsulfonyl)-2-nitroaniline, 2-O2NC6H4NHSO2C6H4I-4′ (6), and the combination of an I...O=S interaction and a hard N—H...O(nitro) hydrogen bond links the two types of molecule to form a cyclic, centrosymmetric four-component aggregate. C—H...O hydrogen bonds link these four-molecule aggregates to form a molecular ladder. Comparisons are made with structures retrieved from the Cambridge Structural Database.

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.

Methyl (3aRS,3cRS,6cSR,7RS,8RS,8aSR)-2,5-bis(4-chlorophenyl)-7,9-bis(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4,6-tetraoxododecahydro-1H-dipyrrolo[3,4-a:3′,4′-f]pyrrolizine-3b-carboxylate dimethylformamide disolvate: a three-dimensional hydrogen-bonded framework

2012 ◽  
Vol 68 (11) ◽  
pp. o439-o442 ◽  
Author(s):  
Jairo Quiroga ◽  
Jaime Gálvez ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Mirror Symmetry ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Envelope Conformation ◽  
Π Stacking ◽  
Conformation Intermediate ◽  
Solvent Molecules ◽  
Molecular Components

The racemic title dipyrrolopyrrolizine compound crystallizes from dimethylformamide as a disolvate, C55H39Cl2N7O6·2C3H7NO. None of the four fused heterocyclic rings is planar; one adopts an envelope conformation, two others adopt half-chair conformations and the fourth adopts a conformation intermediate between an envelope and a half-chair. The arrangement of the ring fusions is such as to preclude the possibility of internal mirror symmetry. The three independent molecular components are weakly linked by C—H...O hydrogen bonds, and the dipyrrolopyrrolizine molecules are linked by a combination of four C—H...O and one C—H...π(arene) hydrogen bond to form a three-dimensional framework, from which the dimethylformamide solvent molecules are pendent. However, aromatic π–π stacking interactions are absent in the structure.

scholarly journals Nine N-aryl-2-chloronicotinamides: supramolecular structures in one, two and three dimensions

2006 ◽  
Vol 62 (4) ◽  
pp. 651-665 ◽  
Author(s):  
Silvia Cuffini ◽  
Christopher Glidewell ◽  
John N. Low ◽  
Aline G. de Oliveira ◽  
Marcus V. N. de Souza ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Supramolecular Structures ◽  
Three Dimensions ◽  
Compound Viii ◽  
Stacking Interactions ◽  
Compound I ◽  
Π Stacking ◽  
Compound Ii

Structures are reported here for eight further substituted N-aryl-2-chloronicotinamides, 2-ClC5H3NCONHC6H4 X-4′. When X = H, compound (I) (C12H9ClN2O), the molecules are linked into sheets by N—H...N, C—H...π(pyridyl) and C—H...π(arene) hydrogen bonds. For X = CH3, compound (II) (C13H11ClN2O, triclinic P\bar 1 with Z′ = 2), the molecules are linked into sheets by N—H...O, C—H...O and C—H...π(arene) hydrogen bonds. Compound (III), where X = F, crystallizes as a monohydrate (C12H8ClFN2O·H2O) and sheets are formed by N—H...O, O—H...O and O—H...N hydrogen bonds and aromatic π...π stacking interactions. Crystals of compound (IV), where X = Cl (C12H8Cl2N2O, monoclinic P21 with Z′ = 4) exhibit inversion twinning: the molecules are linked by N—H...O hydrogen bonds into four independent chains, linked in pairs by C—H...π(arene) hydrogen bonds. When X = Br, compound (V) (C12H8BrClN2O), the molecules are linked into sheets by N—H...O and C—H...N hydrogen bonds, while in compound (VI), where X = I (C12H8ClIN2O), the molecules are linked into a three-dimensional framework by N—H...O and C—H...π(arene) hydrogen bonds and an iodo...N(pyridyl) interaction. For X = CH3O, compound (VII) (C13H11ClN2O2), the molecules are linked into chains by a single N—H...O hydrogen bond. Compound (VIII) (C13H8ClN3O, triclinic P\bar 1 with Z′ = 2), where X = CN, forms a complex three-dimensional framework by N—H...N, C—H...N and C—H...O hydrogen bonds and two independent aromatic π...π stacking interactions.

Reactions between arylhydrazinium chlorides and 2-chloroquinoline-3-carbaldehydes: molecular and supramolecular structures of a hydrazone, a 4,9-dihydro-1H-pyrazolo[3,4-b]quinoline and two 1H-pyrazolo[3,4-b]quinolines

2016 ◽  
Vol 72 (9) ◽  
pp. 670-678 ◽  
Author(s):  
Tholappanavara H. Suresha Kumara ◽  
Gopalpur Nagendrappa ◽  
Nanjappa Chandrika ◽  
Haliwana B. V. Sowmya ◽  
Manpreet Kaur ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Biological Activities ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Compound I ◽  
Space Group ◽  
Π Stacking ◽  
Wide Range ◽  
A Chain

Hydrazone derivatives exhibit a wide range of biological activities, while pyrazolo[3,4-b]quinoline derivatives, on the other hand, exhibit both antimicrobial and antiviral activity, so that all new derivatives in these chemical classes are potentially of value. Dry grinding of a mixture of 2-chloroquinoline-3-carbaldehyde and 4-methylphenylhydrazinium chloride gives (E)-1-[(2-chloroquinolin-3-yl)methylidene]-2-(4-methylphenyl)hydrazine, C17H14ClN3, (I), while the same regents in methanol in the presence of sodium cyanoborohydride give 1-(4-methylphenyl)-4,9-dihydro-1H-pyrazolo[3,4-b]quinoline, C17H15N3, (II). The reactions between phenylhydrazinium chloride and either 2-chloroquinoline-3-carbaldehyde or 2-chloro-6-methylquinoline-3-carbaldehyde give, respectively, 1-phenyl-1H-pyrazolo[3,4-b]quinoline, C16H11N3, (III), which crystallizes in the space groupPbcnas a nonmerohedral twin havingZ′ = 3, or 6-methyl-1-phenyl-1H-pyrazolo[3,4-b]quinoline, C17H13N3, (IV), which crystallizes in the space groupR\overline{3}. The molecules of compound (I) are linked into sheets by a combination of N—H...N and C—H...π(arene) hydrogen bonds, and the molecules of compound (II) are linked by a combination of N—H...N and C—H...π(arene) hydrogen bonds to form a chain of rings. In the structure of compound (III), one of the three independent molecules forms chains generated by C—H...π(arene) hydrogen bonds, with a second type of molecule linked to the chains by a second C—H...π(arene) hydrogen bond and the third type of molecule linked to the chain by multiple π–π stacking interactions. A single C—H...π(arene) hydrogen bond links the molecules of compound (IV) into cyclic centrosymmetric hexamers having \overline{3} (S6) symmetry, which are themselves linked into a three-dimensional array by π–π stacking interactions.

scholarly journals 4-(Diphenylamino)benzaldehyde 4-phenylthiosemicarbazone

2012 ◽  
Vol 68 (8) ◽  
pp. o2402-o2403 ◽  
Author(s):  
Rafael Mendoza-Meroño ◽  
Laura Menéndez-Taboada ◽  
Santiago García-Granda
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Phenyl Ring ◽  
Crystal Packing ◽  
Stacking Interactions ◽  
Π Stacking ◽  
Phenyl Rings ◽  
Π Stacking Interaction ◽  
Title Molecule ◽  
Ring Motif

The title molecule, C26H22N4S, is composed of three main parts,viz.a triphenylamine group is connected to a phenyl ring by a thiosemicarbazone moiety. The C= N double bond has anEconformation. The crystal packing is dominated by strong hydrogen bonds through the thiosemicarbazone moiety, with pairs of N—H...S hydrogen bonds linking the molecules to form inversion dimers with anR22(8) ring motif. An intramolecular N—H...N hydrogen bond is also present, generating anS(5) ring motif. Although the structure contains four phenyl rings, π–π stacking interactions are not formed between them, probably due to the conformation adopted by the triphenylamine group. However, a weak π–π stacking interaction is observed between the phenyl ring and the delocalized thiosemicarbazone moiety.

Contrasting the supramolecular structures in the isomeric pair 5-bromo-3-nitrosalicylaldehyde phenylhydrazone and 3-bromo-5-nitrosalicylaldehyde phenylhydrazone

2013 ◽  
Vol 69 (2) ◽  
pp. 150-155 ◽  
Author(s):  
Ligia R. Gomes ◽  
John Nicolson Low ◽  
James L. Wardell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Hydroxy Group ◽  
Three Dimensional ◽  
Supramolecular Structures ◽  
Zigzag Chain ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Π Stacking ◽  
Independent Molecules

Isomeric 5-bromo-3-nitrosalicylaldehyde phenylhydrazone and 3-bromo-5-nitrosalicylaldehyde phenylhydrazone, C13H10BrN3O3, both crystallize with two molecules in the asymmetric unit. In both isomers, an intramolecular O—H...N hydrogen bond links the hydroxy group and the imine N atom. In the 5-bromo-3-nitro isomer, there are two independent N—H...O hydrogen-bonded chains, each molecule in the asymmetric unit forming its own chain. These chains are then linked to form a three-dimensional framework by a combination of weak C—H...O, C—H...Br, C—H...π and π–π stacking interactions. In the 3-bromo-5-nitro isomer, N—H...O hydrogen bonds link the independent molecules alternately into a zigzag chain, which is reinforced by a weak C—H...O interaction. Individual chains are linked by a C—H...Br interaction and a three-dimensional framework is generated by π–π stacking interactions.

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