Supramolecular structures of three isomeric (E,E)-1-(2-iodophenyl)-4-(nitrophenyl)-2,3-diaza-1,3-butadienes: changes in intermolecular interactions consequent upon changes of substituent location

C Glidewell, J N Low, J M S Skakle, J L Wardell

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Abstract

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, π-π 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.

Original languageEnglish
Pages (from-to)o312-o316
Number of pages5
JournalActa Crystallographica Section C, Crystal Structure Communications
VolumeC61
DOIs
Publication statusPublished - 2005

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Isomers
Hydrogen
Molecules
Hydrogen bonds
4-nitrophenyl
1,3-butadiene

Keywords

  • CENTER-DOT-O
  • PI-STACKING INTERACTIONS
  • SOFT HYDROGEN-BONDS
  • NITRO INTERACTIONS
  • COMBINATION
  • INTERPLAY
  • CRYSTALS
  • 2,4-DINITROPHENYLHYDRAZONE
  • 4-NITROPHENYLHYDRAZONE
  • PATTERNS

Cite this

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title = "Supramolecular structures of three isomeric (E,E)-1-(2-iodophenyl)-4-(nitrophenyl)-2,3-diaza-1,3-butadienes: changes in intermolecular interactions consequent upon changes of substituent location",
abstract = "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, π-π 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.",
keywords = "CENTER-DOT-O, PI-STACKING INTERACTIONS, SOFT HYDROGEN-BONDS, NITRO INTERACTIONS, COMBINATION, INTERPLAY, CRYSTALS, 2,4-DINITROPHENYLHYDRAZONE, 4-NITROPHENYLHYDRAZONE, PATTERNS",
author = "C Glidewell and Low, {J N} and Skakle, {J M S} and Wardell, {J L}",
year = "2005",
doi = "10.1107/S0108270105009248",
language = "English",
volume = "C61",
pages = "o312--o316",
journal = "Acta Crystallographica Section C, Crystal Structure Communications",
issn = "0108-2701",
publisher = "Wiley-Blackwell",

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TY - JOUR

T1 - Supramolecular structures of three isomeric (E,E)-1-(2-iodophenyl)-4-(nitrophenyl)-2,3-diaza-1,3-butadienes: changes in intermolecular interactions consequent upon changes of substituent location

AU - Glidewell, C

AU - Low, J N

AU - Skakle, J M S

AU - Wardell, J L

PY - 2005

Y1 - 2005

N2 - 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, π-π 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.

AB - 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, π-π 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.

KW - CENTER-DOT-O

KW - PI-STACKING INTERACTIONS

KW - SOFT HYDROGEN-BONDS

KW - NITRO INTERACTIONS

KW - COMBINATION

KW - INTERPLAY

KW - CRYSTALS

KW - 2,4-DINITROPHENYLHYDRAZONE

KW - 4-NITROPHENYLHYDRAZONE

KW - PATTERNS

U2 - 10.1107/S0108270105009248

DO - 10.1107/S0108270105009248

M3 - Article

VL - C61

SP - o312-o316

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

ER -