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

C. Glidewell, Janet Mabel Scott Skakle, S. M. S. V. Wardell, J. L. Wardell

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Abstract

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 P2(1)2(1)2(1)] the molecules are linked into sheets by a combination of four independent C - H center dot center dot center dot O hydrogen bonds, but I center dot center dot center dot 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 center dot center dot center dot nitro interaction and one C - H center dot center dot center dot O hydrogen bond into sheets containing R-4(4)(30) rings, while in (III) they are linked by an iodo center dot center dot center dot carbonyl interaction and a C - H center dot center dot center dot 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 center dot center dot center dot nitro interaction, three C - H center dot center dot center dot O hydrogen bonds and an aromatic pi center dot center dot center dot pi stacking interaction, but the framework in ( V) is generated by a two-centre iodo center dot center dot center dot nitro interaction and only two C - H center dot center dot center dot O hydrogen bonds: aromatic pi center dot center dot center dot pi stacking interactions are absent from (V).

Original languageEnglish
Pages (from-to)227-237
Number of pages10
JournalActa Crystallographica Section B, Structural Science
VolumeB61
DOIs
Publication statusPublished - 2005

Keywords

  • CRYSTAL-STRUCTURE PREDICTION
  • SMALL ORGANIC-MOLECULES
  • COMBINATION
  • SHEETS
  • 2,4-DINITROPHENYLHYDRAZONE
  • 4-NITROPHENYLHYDRAZONE
  • PATTERNS
  • RINGS
  • HARD

Cite this

@article{737e28675d0d42928c6a1b33d594a3f1,
title = "Isomeric N-(iodophenyl)nitrophthalimides: interplay of C-H...O hydrogen bonds, iodo...nitro and iodo...carbonyl interactions, and aromatic p...p stacking",
abstract = "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 P2(1)2(1)2(1)] the molecules are linked into sheets by a combination of four independent C - H center dot center dot center dot O hydrogen bonds, but I center dot center dot center dot 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 center dot center dot center dot nitro interaction and one C - H center dot center dot center dot O hydrogen bond into sheets containing R-4(4)(30) rings, while in (III) they are linked by an iodo center dot center dot center dot carbonyl interaction and a C - H center dot center dot center dot 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 center dot center dot center dot nitro interaction, three C - H center dot center dot center dot O hydrogen bonds and an aromatic pi center dot center dot center dot pi stacking interaction, but the framework in ( V) is generated by a two-centre iodo center dot center dot center dot nitro interaction and only two C - H center dot center dot center dot O hydrogen bonds: aromatic pi center dot center dot center dot pi stacking interactions are absent from (V).",
keywords = "CRYSTAL-STRUCTURE PREDICTION, SMALL ORGANIC-MOLECULES, COMBINATION, SHEETS, 2,4-DINITROPHENYLHYDRAZONE, 4-NITROPHENYLHYDRAZONE, PATTERNS, RINGS, HARD",
author = "C. Glidewell and Skakle, {Janet Mabel Scott} and Wardell, {S. M. S. V.} and Wardell, {J. L.}",
year = "2005",
doi = "10.1107/S0108768105004234",
language = "English",
volume = "B61",
pages = "227--237",
journal = "Acta Crystallographica Section B, Structural Science",
issn = "0108-7681",
publisher = "International Union of Crystallography",

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TY - JOUR

T1 - Isomeric N-(iodophenyl)nitrophthalimides: interplay of C-H...O hydrogen bonds, iodo...nitro and iodo...carbonyl interactions, and aromatic p...p stacking

AU - Glidewell, C.

AU - Skakle, Janet Mabel Scott

AU - Wardell, S. M. S. V.

AU - Wardell, J. L.

PY - 2005

Y1 - 2005

N2 - 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 P2(1)2(1)2(1)] the molecules are linked into sheets by a combination of four independent C - H center dot center dot center dot O hydrogen bonds, but I center dot center dot center dot 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 center dot center dot center dot nitro interaction and one C - H center dot center dot center dot O hydrogen bond into sheets containing R-4(4)(30) rings, while in (III) they are linked by an iodo center dot center dot center dot carbonyl interaction and a C - H center dot center dot center dot 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 center dot center dot center dot nitro interaction, three C - H center dot center dot center dot O hydrogen bonds and an aromatic pi center dot center dot center dot pi stacking interaction, but the framework in ( V) is generated by a two-centre iodo center dot center dot center dot nitro interaction and only two C - H center dot center dot center dot O hydrogen bonds: aromatic pi center dot center dot center dot pi stacking interactions are absent from (V).

AB - 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 P2(1)2(1)2(1)] the molecules are linked into sheets by a combination of four independent C - H center dot center dot center dot O hydrogen bonds, but I center dot center dot center dot 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 center dot center dot center dot nitro interaction and one C - H center dot center dot center dot O hydrogen bond into sheets containing R-4(4)(30) rings, while in (III) they are linked by an iodo center dot center dot center dot carbonyl interaction and a C - H center dot center dot center dot 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 center dot center dot center dot nitro interaction, three C - H center dot center dot center dot O hydrogen bonds and an aromatic pi center dot center dot center dot pi stacking interaction, but the framework in ( V) is generated by a two-centre iodo center dot center dot center dot nitro interaction and only two C - H center dot center dot center dot O hydrogen bonds: aromatic pi center dot center dot center dot pi stacking interactions are absent from (V).

KW - CRYSTAL-STRUCTURE PREDICTION

KW - SMALL ORGANIC-MOLECULES

KW - COMBINATION

KW - SHEETS

KW - 2,4-DINITROPHENYLHYDRAZONE

KW - 4-NITROPHENYLHYDRAZONE

KW - PATTERNS

KW - RINGS

KW - HARD

U2 - 10.1107/S0108768105004234

DO - 10.1107/S0108768105004234

M3 - Article

VL - B61

SP - 227

EP - 237

JO - Acta Crystallographica Section B, Structural Science

JF - Acta Crystallographica Section B, Structural Science

SN - 0108-7681

ER -