Interplay of hydrogen bonds, iodo...nitro interactions and aromatic π...π stacking interactions in iodo-nitroanilines

2002 ◽  
Vol 58 (4) ◽  
pp. 701-709 ◽  
Author(s):  
Simon J. Garden ◽  
Silvia P. Fontes ◽  
James L. Wardell ◽  
Janet M. S. Skakle ◽  
John N. Low ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Nitro Group ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Single Type ◽  
Stacking Interactions ◽  
Π Stacking ◽  
Independent Molecules ◽  
Related Compounds ◽  
Centrosymmetric Dimers

Molecules of 2-iodo-5-nitroaniline (I) are linked by N—H...O hydrogen bonds into centrosymmetric dimers and by asymmetric three-centre iodo...nitro interactions into chains, so forming chains of fused centrosymmetric rings: these chains are linked by aromatic π...π stacking interactions to form a three-dimensional structure. In the isomeric 4-iodo-2-nitroaniline (II), each of the two independent molecules forms hydrogen-bonded chains that are linked by two-centre iodo...nitro interactions into sheets of two types, each containing only a single type of molecule: π...π stacking interactions are absent. In 2,4-diiodo-3-nitroaniline (III), where the nitro group is almost orthogonal to the aryl ring, a combination of N—H...O hydrogen bonds and two distinct two-centre iodo...nitro interactions links the molecules into a three-dimensional framework that is reinforced by aromatic π...π stacking interactions. Bond lengths and conformations are discussed and comparisons are drawn with related compounds.

scholarly journals Different patterns of supramolecular assembly in constitutionally similar 6-arylimidazo[2,1-b][1,3,4]thiadiazoles

2014 ◽  
Vol 70 (9) ◽  
pp. 920-926 ◽  
Author(s):  
Aletti S. Praveen ◽  
Hemmige S. Yathirajan ◽  
Manpreet Kaur ◽  
Badiadka Narayana ◽  
Eric C. Hosten ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Reaction Times ◽  
Supramolecular Assembly ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Aryl Group ◽  
Π Stacking ◽  
Related Compounds ◽  
Centrosymmetric Dimers

Four imidazo[2,1-b][1,3,4]thiadiazoles containing a simply-substituted 6-aryl group have been synthesized by reaction of 2-amino-1,3,4-thiadiazoles with bromoacetylarenes using microwave irradiation and brief reaction times. 6-(2-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H6ClN3S, (I), 6-(2-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C11H8ClN3S, (II), 6-(3,4-dichlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H5Cl2N3S, (III), and 6-(4-fluoro-3-methoxyphenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C12H10FN3OS, (IV), crystallize withZ′ values of 2, 1, 1 and 2 respectively. The molecular skeletons are all nearly planar and the dihedral angles between the imidazole and aryl rings are 1.51 (8) and 7.28 (8)° in (I), 9.65 (7)° in (II), 10.44 (8)° in (III), and 1.05 (8) and 7.21 (8)° in (IV). The molecules in (I) are linked by three independent C—H...N hydrogen bonds to form ribbons containing alternatingR22(8) andR44(18) rings, and these ribbons are linked into a three-dimensional array by three independent π-stacking interactions. Both (II) and (III) contain centrosymmetric dimers formed by π-stacking interactions but hydrogen bonds are absent, and the molecules of (IV) are linked into centrosymmetricR22(8) dimers by C—H...N hydrogen bonds. Comparisons are made with a number of related compounds.

Conformational preferences and supramolecular aggregation in 2-nitrophenylthiolates: disulfides and thiosulfonates

2000 ◽  
Vol 56 (5) ◽  
pp. 893-905 ◽  
Author(s):  
Christopher Glidewell ◽  
John N. Low ◽  
James L. Wardell
Keyword(s):  
Hydrogen Bonds ◽  
Nitro Group ◽  
Molecular Conformation ◽  
Three Dimensional ◽  
Asymmetric Unit ◽  
Aryl Ring ◽  
Conformational Preferences ◽  
Independent Molecules ◽  
Centrosymmetric Dimers ◽  
Supramolecular Aggregation

In each of the asymmetrically substituted disulfides 2-nitro-4′-methyldiphenyl disulfide, C13H11NO2S2 (1), 2-nitro-4′-chlorodiphenyl disulfide, C12H8ClNO2S2 (2), 2,4-dinitro-4′-methyldiphenyl disulfide, C13H10N2O4S2 (3), and 2,4-dinitrophenyl-2′-methoxycarbonylmethyl disulfide, C9H8N2O6S2 (4), and in both of the symmetrically substituted disulfides bis(2-nitrophenyl) disulfide, C12H8N2O4S2 (5), and bis(2-nitro-4-trifluoromethylphenyl) disulfide, C14H6F6N2O4S2 (6), the 2-nitro groups are essentially coplanar with the adjacent aryl ring and the S atom remote from the nitrated aryl ring is also essentially coplanar and transoid to the nitro group. In S-(2-nitrophenyl) 2-nitrobenzene thiosulfonate, C12H8N2O6S2 (7), which contains three independent molecules in the asymmetric unit, all six of the independent nitro groups are twisted out of the plane of the adjacent aryl rings. The crystal structures of (1)–(3) contain isolated molecules, that of (4) contains centrosymmetric dimers held together by C—H...O hydrogen bonds, while in the structures of (5)—(7), respectively, the C—H...O hydrogen bonds generate one-, two- and three-dimensional arrays. The interplay between molecular conformation and supramolecular aggregation is discussed.

Nine isomeric nitrobenzylidene-iodoanilines: interplay of C—H...O hydrogen bonds, iodo...nitro interactions and aromatic π...π stacking interactions

2002 ◽  
Vol 58 (5) ◽  
pp. 864-876 ◽  
Author(s):  
Christopher Glidewell ◽  
R. Alan Howie ◽  
John N. Low ◽  
Janet M. S. Skakle ◽  
Solange M. S. V. Wardell ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Dimensional Structure ◽  
Stacking Interactions ◽  
Three Dimensional Structure ◽  
Π Stacking ◽  
Isolated Molecules

Nine isomeric nitrobenzylidene-iodoanilines, O2NC6H4CH= NC6H4I [(I)–(IX)], have been synthesized and the structures of all except 4-nitrobenzylidene-4′-iodoaniline (IX) have been analyzed. 2-Nitrobenzylidene-2′-iodoaniline (I) contains isolated molecules, while 3-nitrobenzylidene-2′-iodoaniline (II) and 2-nitrobenzylidene-3′-iodoaniline (IV) both contain chains of molecules linked by C—H...O hydrogen bonds: similar chains in 4-nitrobenzylidene-2′-iodoaniline (III) are further linked by aromatic π...π stacking interactions, forming sheets. In both 3-nitrobenzylidene-3′-iodoaniline and 4-nitrobenzylidene-3′-iodoaniline, (V) and (VI), a combination of C—H...O hydrogen bonds and iodo...nitro interactions generates molecular ladders that are linked into sheets by aromatic π...π stacking interactions, while in 2-nitrobenzylidene-4′-iodoaniline and 3-nitrobenzylidene-4′-iodoaniline, (VII) and (VIII), which both crystallize with Z′ = 2 in C2/c and P\bar 1, respectively, the combination of C—H...O hydrogen bonds and iodo...nitro interactions generates sheets, which in (VIII) are further linked by π...π stacking interactions to form a three-dimensional structure. The 4,4′-isomer (IX) crystallizes in Fdd2 with Z′ = 2, but both molecules are intractably disordered.

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.

scholarly journals Crystal structures of five (2-chloroquinolin-3-yl)methyl ethers: supramolecular assembly in one and two dimensions mediated by hydrogen bonding and π–π stacking

2015 ◽  
Vol 71 (6) ◽  
pp. 609-617 ◽  
Author(s):  
Haliwana B. V. Sowmya ◽  
Tholappanavara H. Suresha Kumara ◽  
Nagendrappa Gopalpur ◽  
Jerry P. Jasinski ◽  
Sean P. Millikan ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Supramolecular Assembly ◽  
Two Dimensions ◽  
Single Type ◽  
Stacking Interactions ◽  
The Third ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Independent Molecules

In the molecules of the title compounds, methyl 5-bromo-2-[(2-chloroquinolin-3-yl)methoxy]benzoate, C18H13BrClNO3, (I), methyl 5-bromo-2-[(2-chloro-6-methylquinolin-3-yl)methoxy]benzoate, C19H15BrClNO3, (II), methyl 2-[(2-chloro-6-methylquinolin-3-yl)methoxy]benzoate, C19H16ClNO3, (III), which crystallizes withZ′ = 4 in space groupP212121, and 2-chloro-3-[(naphthalen-1-yloxy)methyl]quinoline, C20H14ClNO, (IV), the non-H atoms are nearly coplanar, but in {5-[(2-chloroquinolin-3-yl)methoxy]-4-(hydroxymethyl)-6-methylpyridin-3-yl}methanol, C18H17ClN2O3, (V), the planes of the quinoline unit and of the unfused pyridine ring are almost parallel, although not coplanar. The molecules of (I) are linked by two independent π–π stacking interactions to form chains, but there are no hydrogen bonds present in the structure. In (II), the molecules are weakly linked into chains by a single type of π–π stacking interaction. In (III), three of the four independent molecules are linked by π–π stacking interactions but the other molecule does not participate in such interactions. Weak C—H...O hydrogen bonds link the molecules into three types of chains, two of which contain just one type of independent molecule while the third type of chain contains two types of molecule. The molecules of (IV) are linked into chains by a C—H...π(arene) hydrogen bond, but π–π stacking interactions are absent. In (V), there is an intramolecular O—H...O hydrogen bond, and molecules are linked into sheets by a combination of O—H...N hydrogen bonds and π–π stacking interactions.

scholarly journals Crystal structure of 2-bromo-1,4-dihydroxy-9,10-anthraquinone

2014 ◽  
Vol 70 (10) ◽  
pp. o1130-o1130 ◽  
Author(s):  
Wataru Furukawa ◽  
Munenori Takehara ◽  
Yoshinori Inoue ◽  
Chitoshi Kitamura
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Compound C ◽  
Π Stacking ◽  
Dimensional Network

In an attempt to brominate 1,4-dipropoxy-9,10-anthraquinone, a mixture of products, including the title compound, C14H7BrO4, was obtained. The molecule is essentially planar (r.m.s. deviation = 0.029 Å) and two intramolecular O—H...O hydrogen bonds occur. In the crystal, the molecules are linked by weak C—H...O hydrogen bonds, Br...O contacts [3.240 (5) Å], and π–π stacking interactions [shortest centroid–centroid separation = 3.562 (4) Å], generating a three-dimensional network.

scholarly journals 7-Nitro-2-phenylimidazo[2,1-b][1,3]benzothiazole

2014 ◽  
Vol 70 (2) ◽  
pp. o143-o144 ◽  
Author(s):  
Alexander S. Bunev ◽  
Elena V. Sukhonosova ◽  
Vladimir E. Statsyuk ◽  
Gennady I. Ostapenko ◽  
Victor N. Khrustalev
Keyword(s):  
Nitro Group ◽  
Phenyl Ring ◽  
Three Dimensional ◽  
Interplanar Distance ◽  
Stacking Interactions ◽  
Π Stacking ◽  
The Mean ◽  
Title Molecule

In the title molecule, C15H9N3O2S, the central imidazo[2,1-b][1,3]benzothiazole heterotricyclic unit is essentially planar (r.m.s. deviation = 0.021 Å). The terminal phenyl ring and nitro group are twisted by 9.06 (1) and 11.02 (4)°, respectively, from the mean plane of the heterotricycle. In the crystal, molecules are linked by π–π stacking interactions into columns along [100]; the interplanar distance between neighboring imidazo[2,1-b][1,3]benzothiazole planes within the columns is 3.370 (2) Å. Furthermore, the columns interact with each other by secondary S...O [2.9922 (10) and 3.1988 (11) Å] interactions, forming a three-dimensional framework.

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.

Crystal structures and Hirshfeld surface analysis of four 1,4-bis(methoxyphenyl)-2,3-diazabuta-1,3-dienes: comparisons of the intermolecular interactions in related compounds

2019 ◽  
Vol 234 (1) ◽  
pp. 59-71 ◽  
Author(s):  
Ligia R. Gomes ◽  
John N. Low ◽  
Nathasha R. de L. Correira ◽  
Thais C.M. Noguiera ◽  
Alessandra C. Pinheiro ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Intermolecular Interactions ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Dimensional Structure ◽  
Intermolecular Hydrogen Bonds ◽  
Π Interactions ◽  
Isomeric Compound ◽  
Related Compounds

Abstract The crystal structures of four azines, namely 1-3-bis(4-methoxyphenyl)-2,3-diaza-1,4-butadiene, 1, 1,3-bis(2,3-dimethoxyphenyl)-2,3-diaza-1,4-butadiene, 2, 1,3-bis(2-hydroxy-3-methoxyphenyl)-2,3-diaza-1,4-butadiene, 3, and 1,3-bis(2-hydroxy-4-methoxyphenyl)-2,3-diaza-1,4-butadiene, 4, are reported. Molecules of 3 and 4, and both independent molecules of 2, Mol A and Mol B, possess inversion centers. The central C=N–N=C units in each molecule is planar with an (E,E) conformation. The intermolecular interactions found in the four compounds are C–H···O, C–H–N, C–H---π and π---π interactions. However, there is no consistent set of intermolecular interactions for the four compounds. Compound, 1, has a two-dimensional undulating sheet structure, generated from C–H···O and C–H···N intermolecular hydrogen bonds. The only recognized intermolecular interaction in 2 is a C–H···O hydrogen bond, which results in a zig-zag chain of alternating molecules, Mol A and Mol B. While 3 forms a puckered sheet of molecules, solely via C–H···π interactions, its isomeric compound, 4, has a more elaborate three-dimensional structure generated from a combination of C–H···O hydrogen bonds, C–H···π and π···π interactions. The findings in this study, based on both PLATON and Hirshfeld approaches, for the four representative compounds match well the reported structural findings in the literature of related compounds, which are based solely on geometric parameters.

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