Isomeric N -(iodophenyl)nitrophthalimides: interplay of C—H...O hydrogen bonds, iodo...nitro and iodo...carbonyl interactions, and aromatic π...π stacking interactions (original) (raw)
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Isomeric nitrophthalimides: sheets built from N-H...O and C-H...O hydrogen bonds
Acta crystallographica. Section C, Crystal structure communications, 2004
Molecules of 3-nitrophthalimide, C(8)H(4)N(2)O(4), are linked into sheets by a combination of one N-H...O hydrogen bond [H...O = 1.99 angstroms, N...O = 2.8043 (14) angstroms and N-H...O = 176 degrees] and two independent C-H...O hydrogen bonds [H...O = 2.36 and 2.56 angstroms, C...O = 3.1639 (16) and 3.4386 (16) angstroms, and C-H...O = 142 and 153 degrees], and these sheets are linked into pairs by a single pi-pi stacking interaction. Molecules of isomeric 4-nitrophthalimide are linked into sheets by a combination of one three-centre N-H...(O)(2) hydrogen bond [H...O = 2.14 and 2.55 angstroms, N...O = 2.974 (3) and 3.231 (3) angstroms, N-H...O = 151 and 131 degrees, and O...H...O = 76 degrees] and two independent two-centre C-H...O hydrogen bonds [H...O = 2.38 and 2.54 angstroms, C...O = 3.257 (4) and 3.452 (4) angstroms, and C-H...O = 156 and 168 degrees].
Acta Crystallographica Section C-crystal Structure Communications, 2003
nation of these two ions might therefore be reasonably expected to give rise to a planar supramolecular system. Cocrystallization of piperazine and squaric acid from organic solvents such as light alcohols, acetone or tetrahydrofuran gave extremely rapid precipitation of very tiny crystals wholly unsuitable for single-crystal X-ray diffraction, presumably because of the rather low solubility of the ionic product in these solvents. Cocrystallization from water, however, provided excellent crystals of the dihydrate, (C4H12N4)2+'(C404) 2-'-2H20, (1), whose structure is reported here.
Acta Crystallographica Section B Structural Science, 2004
Molecules of 2-iodo-N-(4-nitrobenzyl)aniline, 4-O2NC6H4CH2NHC6H4I-2′ (1) are linked into chains by C—H...O hydrogen bonds. In the isomeric compound 3-iodo-N-(4-nitrobenzyl)aniline (2) a combination of N—H...O and C—H...O hydrogen bonds and iodo...nitro and aromatic π...π stacking interactions links the molecules into a three-dimensional framework structure. The two-dimensional supramolecular structure of 4-iodo-N-(4-nitrobenzyl)aniline (6) is built from a combination of C—H...O and N—H...π(arene) hydrogen bonds and aromatic π...π stacking interactions. 2-Iodo-N-(2-nitrobenzyl)aniline (7) crystallizes with two molecules in the asymmetric unit and these molecules are linked into ladders by a combination of N—H...O and C—H...O hydrogen bonds and iodo...nitro and aromatic π...π stacking interactions. Comparisons are made between the supramolecular structures of these compounds and those of other isomers, in terms both of the types of direction-specific intermolecular interactions exhibi...
Acta crystallographica. Section C, Crystal structure communications, 2002
In 2,6-diiodo-4-nitrophenol, C(6)H(3)I(2)NO(3), the molecules are linked, by an O-H...O hydrogen bond and two iodo-nitro interactions, into sheets, which are further linked into a three-dimensional framework by aromatic pi-pi-stacking interactions. The molecules of 2,6-diiodo-4-nitrophenyl acetate, C(8)H(5)I(2)NO(4), lie across a mirror plane in space group Pnma, with the acetyl group on the mirror, and they are linked by a single iodo-nitro interaction to form isolated sheets. The molecules of 2,6-diiodo-4-nitroanisole, C(7)H(5)I(2)NO(3), are linked into isolated chains by a single two-centre iodo-nitro interaction.
N-(4-fluorophenyl)-4-nitrophthalimide: tripartite hydrogen-bonded sheets
Acta crystallographica. Section C, Crystal structure communications, 2004
Molecules of the title compound, C14H7FN2O4, are linked by two C-H...O hydrogen bonds [H...O = 2.42 and 2.44 A, C...O = 3.173 (9) and 3.313 (10) A, and C-H...O = 134 and 157 degrees] into deep tripartite sheets, where the central layer is built from hydrogen-bonded R(6)6(24) rings and where the F atoms all lie on the exterior surfaces of the sheets.
Acta Crystallographica Section B Structural Science, 2002
Nine isomeric nitrobenzylidene-iodoanilines, O 2 NC 6 H 4 CH NC 6 H 4 I [(I)±(IX)], have been synthesized and the structures of all except 4-nitrobenzylidene-4 H-iodoaniline (IX) have been analyzed. 2-Nitrobenzylidene-2 H-iodoaniline (I) contains isolated molecules, while 3-nitrobenzylidene-2 H-iodoaniline (II) and 2-nitrobenzylidene-3 H-iodoaniline (IV) both contain chains of molecules linked by CÐHÁ Á ÁO hydrogen bonds: similar chains in 4-nitrobenzylidene-2 H-iodoaniline (III) are further linked by aromatic %Á Á Á% stacking interactions, forming sheets. In both 3-nitrobenzylidene-3 H-iodoaniline and 4-nitrobenzylidene-3 H-iodoaniline, (V) and (VI), a combination of CÐHÁ Á ÁO hydrogen bonds and iodoÁ Á Ánitro interactions generates molecular ladders that are linked into sheets by aromatic %Á Á Á% stacking interactions, while in 2-nitrobenzylidene-4 H-iodoaniline and 3-nitrobenzylidene-4 Hiodoaniline, (VII) and (VIII), which both crystallize with Z H = 2 in C2/c and P " 1, respectively, the combination of CÐHÁ Á ÁO hydrogen bonds and iodoÁ Á Ánitro interactions generates sheets, which in (VIII) are further linked by %Á Á Á% stacking interactions to form a three-dimensional structure. The 4,4 H-isomer (IX) crystallizes in Fdd2 with Z H = 2, but both molecules are intractably disordered.
Chemistry of Materials, 1997
The synthesis, characterization, and crystal chemistry of N,N′-diphenylisophthalamide (1) and pyridine-2,6-dicarboxylic acid bisphenylamide (2) are described. Through a combination of single-crystal X-ray diffraction and molecular orbital and crystal packing calculations, the important intermolecular interactions have been determined. The structures have been compared with the closely related structures, N,N′-bis(3-hydroxyphenyl)isophthalamide (3) and N,N′-dimethyl-N,N′-diphenylisophthalamide (4). Crystalline 1 and 2 are isostructural, but there are subtle differences in the conformations and packing as a consequence of intramolecular hydrogen bonding in 2. This reduces the deviation from planarity in the molecular conformation of 2 and consequently lengthens the intermolecular hydrogen bonding distances. This is reflected in the lattice energies of 1 and 2 (-40.9 and-38.7 kcal/mol, respectively) and in the stacking energies of these compounds. For the compounds that do not contain an N atom in the central ring the progression 3, 1, 4 represents a reduction in the hydrogen-bonding options, reflected in the respective lattice energies:-51.3,-40.9, and-33.3 kcal/mol. The difference between 3 and 1 is in excellent agreement with predictions based on group contributions in structure 3. In 4 there are no hydrogen bonding options and so C-H‚‚‚O interactions play a much more important role.
Acta crystallographica. Section C, Crystal structure communications, 2005
The supramolecular structures of the three isomeric (E,E)-1-(2-iodophenyl)-4-(2/3/4-nitrophenyl)-2,3-diaza-1,3-butadienes, C14H10IN3O2, are compared. In the 2-nitro isomer, the molecules are disordered across centres of inversion in space group C2/c and are linked into chains by a two-centre iodo-nitro interaction. The molecules of the 3-nitro isomer are linked into a three-dimensional framework by a combination of C-H...O and C-H...I hydrogen bonds and aromatic pi-pi stacking interactions, while molecules of the 4-nitro isomer are linked into sheets by a C-H...O hydrogen bond and a two-centre iodo-nitro interaction.