A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone

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

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Abstract

Molecules of 2-iodobenzaldehyde 4-nitrophenylhydrazone, C13H10IN3O2, are effectively planar and are linked by an N-H...O hydrogen bond [H...O=2.04 Angstrom, N...O=2.905 (6) Angstrom and NDH...O=166degrees] and a two-centre iodo-nitro interaction [I...O=3.361 (4) Angstrom] into a chain of edge-fused R-3(3) (18) rings. There are no direction-specific interactions between adjacent chains. Molecules of 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone, C13H9IN4O4, are disordered over two orientations with occupancies of 0.681 (5) and 0.319 (5). In the major orientation, there are no direction-specific intermolecular interactions, while for the minor form, a single C-H...O hydrogen bond generates centrosymmetric dimers.

Original languageEnglish
Pages (from-to)o98-o101
Number of pages4
JournalActa Crystallographica Section C, Crystal Structure Communications
VolumeC59
DOIs
Publication statusPublished - 2003

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Hydrogen
Hydrogen bonds
Molecules
Dimers
2,4-dinitrophenylhydrazone
Direction compound

Keywords

  • pi-stacking interactions
  • interlay

Cite this

@article{f51f61190ca045c69e063a52f461ca58,
title = "A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone",
abstract = "Molecules of 2-iodobenzaldehyde 4-nitrophenylhydrazone, C13H10IN3O2, are effectively planar and are linked by an N-H...O hydrogen bond [H...O=2.04 Angstrom, N...O=2.905 (6) Angstrom and NDH...O=166degrees] and a two-centre iodo-nitro interaction [I...O=3.361 (4) Angstrom] into a chain of edge-fused R-3(3) (18) rings. There are no direction-specific interactions between adjacent chains. Molecules of 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone, C13H9IN4O4, are disordered over two orientations with occupancies of 0.681 (5) and 0.319 (5). In the major orientation, there are no direction-specific intermolecular interactions, while for the minor form, a single C-H...O hydrogen bond generates centrosymmetric dimers.",
keywords = "pi-stacking interactions, interlay",
author = "C Glidewell and Low, {J N} and Skakle, {J M S} and Wardell, {J L}",
year = "2003",
doi = "10.1107/S0108270103001379",
language = "English",
volume = "C59",
pages = "o98--o101",
journal = "Acta Crystallographica Section C, Crystal Structure Communications",
issn = "0108-2701",
publisher = "Wiley-Blackwell",

}

TY - JOUR

T1 - A chain of edge-fused rings generated by the combination of an N-H center dot center dot center dot O hydrogen bond and an iodo-nitro interaction in 2-iodobenzaldehyde 4-nitrophenylhydrazone versus disordered and effectively isolated molecules in 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone

AU - Glidewell, C

AU - Low, J N

AU - Skakle, J M S

AU - Wardell, J L

PY - 2003

Y1 - 2003

N2 - Molecules of 2-iodobenzaldehyde 4-nitrophenylhydrazone, C13H10IN3O2, are effectively planar and are linked by an N-H...O hydrogen bond [H...O=2.04 Angstrom, N...O=2.905 (6) Angstrom and NDH...O=166degrees] and a two-centre iodo-nitro interaction [I...O=3.361 (4) Angstrom] into a chain of edge-fused R-3(3) (18) rings. There are no direction-specific interactions between adjacent chains. Molecules of 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone, C13H9IN4O4, are disordered over two orientations with occupancies of 0.681 (5) and 0.319 (5). In the major orientation, there are no direction-specific intermolecular interactions, while for the minor form, a single C-H...O hydrogen bond generates centrosymmetric dimers.

AB - Molecules of 2-iodobenzaldehyde 4-nitrophenylhydrazone, C13H10IN3O2, are effectively planar and are linked by an N-H...O hydrogen bond [H...O=2.04 Angstrom, N...O=2.905 (6) Angstrom and NDH...O=166degrees] and a two-centre iodo-nitro interaction [I...O=3.361 (4) Angstrom] into a chain of edge-fused R-3(3) (18) rings. There are no direction-specific interactions between adjacent chains. Molecules of 2-iodobenzaldehyde 2,4-dinitrophenylhydrazone, C13H9IN4O4, are disordered over two orientations with occupancies of 0.681 (5) and 0.319 (5). In the major orientation, there are no direction-specific intermolecular interactions, while for the minor form, a single C-H...O hydrogen bond generates centrosymmetric dimers.

KW - pi-stacking interactions

KW - interlay

U2 - 10.1107/S0108270103001379

DO - 10.1107/S0108270103001379

M3 - Article

VL - C59

SP - o98-o101

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

SN - 0108-2701

ER -