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

Abstract

The six isomeric N-(iodophenyl)nitrophthalimides, C(14)H(7)IN(2)O(4), have been synthesized and the structures of five of them are reported. In N-(4-iodophenyl)-4-nitrophthalimide [(I), orthorhombic P2(1)2(1)2(1)] 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 P2(1)/c] and N-(2-iodophenyl)-4-nitrophthalimide [(III), monoclinic P2(1)/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 P2(1)/n] and N-(3-iodophenyl)-3-nitrophthalimide [(V), orthorhombic, P2(1)2(1)2(1)]. In (IV) the molecules are linked by a three-centre iodo...nitro interaction, three C-H...O hydrogen bonds and an aromatic pi...pi 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 pi...pi stacking interactions are absent from (V).

Steric Control in the Synthesis of Phosphinous Acid-Coordinated Mono- and Binuclear Platinum(II) Complexes

“…This ionic bond character, in agreement with the longer Pt−Cl(1) length observed (2.398 Å) compared with Pt−Cl(2) (2.390 Å), suggested that the chlorine atom is involved in a weaker CH···Cl bond. Moreover, the distance between nitrogen and chlorine atoms (3.179 Å) is in agreement with typical distances N···Cl (2.91−3.52 Å) …”

“…The third kind of hydrogen bond, which involved a C−H---O interaction, , is well established. , These interactions are not restricted to small molecules but have also been reported for biological systems such as proteins, nucleic acids, and carbohydrates . Moreover, these interactions can persist in liquid phase .…”

Structure-Directing Weak Interactions with 1,4-Diiodotetrafluorobenzene Convert One-Dimensional Arrays of [MII(acac)2] Species into Three-Dimensional Networks

“…Relevant bifurcated halogen bonding C–I···μ 2 -(O,O) was repeatedly reported. − Our CCDC search also allowed the verification of FIB-free structures where BXBs span 3–6-membered systems, viz. 3-membered cycles C–I···μ 2 -(O,O)-(ROOR), 4-membered systems C–I···μ 2 -(O,O)-(OXO) (where X = N, ,,,− C, S, , Cl, or such metal centers as Co, Cd, Cu), 5-membered moieties C–I···μ 2 -(O,O)-(OXXO) (X–X = C–C ,, ), and 6-membered species C–I···μ 2 -(O,O)-(OXXXO) (X–X–X = N–C–C, S–N–S). As far as metal-containing fragments C–I···μ 2 -(O,O)-(OMO) ,, (Figure ) are concerned, all these moieties are formed by bifunctional complexes featuring both XB donor (iodine) and XB acceptor (oxygen) centers in one molecule, whereas in our cases supramolecular organization is determined by an external XB donor (the iodines of FIB) and two oxygen centers of each of the acac complexes.…”

Structural study of three o-hydroxyacetophenone derivatives using X-ray powder diffraction: interplay of weak intermolecular interactions

“…4 Desiraju and coworkers have demonstrated various supramolecular synthons based on C-H/O interactions. 5,6 The effectiveness of C-H/p hydrogen bonds has been reviewed on the basis of crystallographic findings and Cambridge Structural Database (CSD) analyses. 7 It is thus useful to design new compounds comprising a rigid core with multiple donor atoms and having different substitutions, and to study their structural features as well as the interplay of weak interactions in building possible supramolecular assemblies.…”