scholarly journals The crystal structures of three disordered 2-substituted benzimidazole esters

2021 ◽  
Vol 77 (5) ◽  
pp. 473-479
Author(s):  
Chayanna Harish Chinthal ◽  
Hemmige S. Yathirajan ◽  
Nagaraja Manju ◽  
Balakrishna Kalluraya ◽  
Sabine Foro ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Stacking Interaction ◽  
Π Stacking ◽  
Donor And Acceptor ◽  
Π Stacking Interaction ◽  
Related Compounds

The crystal structures of three benzimidazole esters containing aryl or heterocyclic substituents at position 2 are reported, and all three exhibit disorder of molecular entities. In ethyl 1-methyl-2-[4-(prop-2-ynoxy)phenyl]-1H-benzimidazole-5-carboxylate, C20H18N2O3, (I), the prop-2-yn-1-oxyphenyl unit is disordered over two sets of atomic sites having effectively equal occupancies, 0.506 (5) and 0.494 (5). The propyl substituent in ethyl 1-propyl-2-(pyren-1-yl)-1H-benzimidazole-5-carboxylate, C29H24N2O2, (II), is disordered over two sets of atomic sites having occupancies 0.601 (8) and 0.399 (8), and the ester unit in ethyl 1-methyl-2-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1H-benzimidazole-5-carboxylate, C21H19ClN4O2 (III), is disordered over two sets of atomic sites having occupancies 0.645 (7) and 0.355 (7). In each of the C—H...π(arene) hydrogen bonds in (I), the donor and acceptor form parts of different disorder components, so that no continuous aggregation is possible. The molecules of (II) are linked by a single C—H...O hydrogen bond into C(10) chains, which are linked into sheets by a π–π stacking interaction, whereas those of (III) are just linked into C(13) chains, again by a single C—H...O hydrogen bond. Comparisons are made with the structures of some related compounds.

scholarly journals Six 1-aroyl-4-(4-methoxyphenyl)piperazines: similar molecular structures but different patterns of supramolecular assembly

2019 ◽  
Vol 75 (8) ◽  
pp. 1253-1260 ◽  
Author(s):  
Haruvegowda Kiran Kumar ◽  
Hemmige S. Yathirajan ◽  
Belakavadi K. Sagar ◽  
Sabine Foro ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Supramolecular Assembly ◽  
Molecular Structures ◽  
Benzoic Acids ◽  
Coupling Reactions ◽  
Stacking Interaction ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Related Compounds

Six new 1-aroyl-4-(4-methoxyphenyl)piperazines have been prepared, using coupling reactions between benzoic acids and N-(4-methoxyphenyl)piperazine. There are no significant hydrogen bonds in the structure of 1-benzoyl-4-(4-methoxyphenyl)piperazine, C18H20N2O2, (I). The molecules of 1-(2-fluorobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19FN2O2, (II), are linked by two C—H...O hydrogen bonds to form chains of rings, which are linked into sheets by an aromatic π–π stacking interaction. 1-(2-Chlorobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19ClN2O2, (III), 1-(2-bromobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19BrN2O2, (IV), and 1-(2-iodobenzoyl)-4-(4-methoxyphenyl)piperazine, C18H19IN2O2, (V), are isomorphous, but in (III) the aroyl ring is disordered over two sets of atomic sites having occupancies of 0.942 (2) and 0.058 (2). In each of (III)–(V), a combination of two C—H...π(arene) hydrogen bonds links the molecules into sheets. A single O—H...O hydrogen bond links the molecules of 1-(2-hydroxybenzoyl)-4-(4-methoxyphenyl)piperazine, C18H20N2O3, (VI), into simple chains. Comparisons are made with the structures of some related compounds.

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.

Hydrogen-bonded bilayers in 7-benzyl-3-tert-butyl-1-phenyl-4,5,6,7-tetrahydro-1H-spiro[pyrazolo[3,4-b]pyridine-5,2′-indan]-1′,3′-dione

2013 ◽  
Vol 69 (8) ◽  
pp. 884-887 ◽  
Author(s):  
Jairo Quiroga ◽  
Dayana Pantoja ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Pyridine Ring ◽  
Stacking Interaction ◽  
Tert Butyl ◽  
Compound C ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Conformation Intermediate

In the title compound, C31H29N3O2, the reduced pyridine ring adopts a conformation intermediate between the envelope and half-chair forms. The aryl rings of the benzyl and phenyl substituents are nearly parallel and overlap, indicative of an intramolecular π–π stacking interaction. A combination of two C—H...O hydrogen bonds and one C—H...N hydrogen bond links the molecules into a bilayer havingtert-butyl groups on both faces.<!?tpb=19.5pt>

Hydrogen-bonded sheet structures in methyl 4-(4-chloroanilino)-3-nitrobenzoate and methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate

2012 ◽  
Vol 69 (1) ◽  
pp. 77-81
Author(s):  
Edwar Cortés ◽  
Rodrigo Abonía ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Stacking Interactions ◽  
Electronic Polarization ◽  
Stacking Interaction ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Hydrogen Bonded

In methyl 4-(4-chloroanilino)-3-nitrobenzoate, C14H11ClN2O4, (I), there is an intramolecular N—H...O hydrogen bond and the intramolecular distances provide evidence for electronic polarization of theo-quinonoid type. The molecules are linked into sheets built from N—H...O, C—H...O and C—H...π(arene) hydrogen bonds, together with an aromatic π–π stacking interaction. The molecules of methyl 1-benzyl-2-(4-chlorophenyl)-1H-benzimidazole-5-carboxylate, C22H17ClN2O2, (II), are also linked into sheets, this time by a combination of C—H...π(arene) hydrogen bonds and aromatic π–π stacking interactions.

2-(4-Methylbenzoyloxymethyl)-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)tetrahydrofuran-3-yl 4-methylbenzoate

2007 ◽  
Vol 63 (3) ◽  
pp. o1395-o1397 ◽  
Author(s):  
H. S. Yathirajan ◽  
Anil N. Mayekar ◽  
B. K. Sarojini ◽  
B. Narayana ◽  
Michael Bolte
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Crystal Packing ◽  
Geometric Parameters ◽  
Stacking Interaction ◽  
Compound C ◽  
Π Stacking ◽  
Π Stacking Interaction

The title compound, C26H26N2O7, is a thiamidine derivative. Geometric parameters are in the usual ranges. The crystal packing is stabilized by a classical N—H...O hydrogen bond, several weak C—H...O hydrogen bonds and a π–π stacking interaction.

scholarly journals Isomeric N-(iodophenyl)nitrobenzamides form different three-dimensional framework structures

2006 ◽  
Vol 62 (5) ◽  
pp. 931-943 ◽  
Author(s):  
James L. Wardell ◽  
John N. Low ◽  
Janet M. S. Skakle ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Supramolecular Structure ◽  
Three Dimensional ◽  
Space Group ◽  
Stacking Interaction ◽  
Π Stacking ◽  
Π Stacking Interaction

The isomeric N-(iodophenyl)nitrobenzamides, C13H9IN2O3, all form different three-dimensional framework structures. Molecules of N-(2-iodophenyl)-3-nitrobenzamide (II) are linked by a combination of N—H...O and C—H...O hydrogen bonds and a two-centre iodo...carbonyl interaction. The supramolecular structure of N-(2-iodophenyl)-4-nitrobenzamide (III) is built from one N—H...O and two C—H...O hydrogen bonds, but short I...O contacts are absent from the structure. In N-(3-iodophenyl)-2-nitrobenzamide (IV), which crystallizes with Z′ = 2 in space group P21, the structure contains two N—H...O hydrogen bonds, four C—H...O hydrogen bonds, two two-centre iodo...nitro interactions and an aromatic π...π stacking interaction. The structure of N-(3-iodophenyl)-3-nitrobenzamide (V) contains one N—H...O hydrogen bond and three C—H...O hydrogen bonds, together with a two-centre iodo...nitro interaction and an aromatic π...π stacking interaction, while in N-(3-iodophenyl)-4-nitrobenzamide (VI), the combination of one N—H...O hydrogen bond and two C—H...O hydrogen bonds is augmented not only by a two-centre iodo...nitro interaction and an aromatic π...π stacking interaction, but also by a dipolar carbonyl...carbonyl interaction. In the supramolecular structure of N-(4-iodophenyl)-4-nitrobenzamide (IX), which crystallizes with Z′ = 2 in space group P\overline 1, there are two N—H...O hydrogen bonds, four C—H...O hydrogen bonds and two three-centre iodo...nitro interactions.

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 Crystal structures of two 6-(2-hydroxybenzoyl)-5H-thiazolo[3,2-a]pyrimidin-5-ones

2015 ◽  
Vol 71 (7) ◽  
pp. 766-771
Author(s):  
Ligia R. Gomes ◽  
John Nicolson Low ◽  
Fernando Cagide ◽  
Fernanda Borges
Keyword(s):  
Hydrogen Bond ◽  
Carboxylic Acid ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Mechanism Of Formation ◽  
Π Stacking ◽  
Heterocyclic Moiety

The title compounds, 6-(2-hydroxybenzyl)-5H-thiazolo[3,2-a]pyrimidin-5-one, C13H8N2O3S, (1), and 6-(2-hydroxybenzyl)-3-methyl-5H-thiazolo[3,2-a]pyrimidin-5-one, C14H10N2O3S, (2), were synthesized when a chromone-3-carboxylic acid, activated with (benzotriazol-1-yloxy)tripyrrolidinylphosphonium hexafluoridophosphate (PyBOP), was reacted with a primary heteromamine. Instead of the expected amidation, the unusual title thiazolopyrimidine-5-one derivatives were obtained serendipitously and a mechanism of formation is proposed. Both compounds present an intramolecular O—H...O hydrogen bond, which generates anS(6) ring. The dihedral angles between the heterocyclic moiety and the 2-hydroxybenzoyl ring are 55.22 (5) and 46.83 (6)° for (1) and (2), respectively. In the crystals, the molecules are linked by weak C—H...O hydrogen bonds and π–π stacking interactions.

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