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

doi:10.1107/S0108270103001379

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

School of Chemistry

Research output: Contribution to journal › Article › peer-review

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 language	English
Number of pages	4
Journal	Acta Crystallographica Section C-Crystal Structure Communications
Volume	59
DOIs	https://doi.org/10.1107/S0108270103001379
Publication status	Published - Mar 2003

Keywords

PI-STACKING INTERACTIONS
INTERPLAY

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Glidewell, C., Low, J. N., Skakle, J. M. S., & Wardell, J. L. (2003). 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. Acta Crystallographica Section C-Crystal Structure Communications, 59. https://doi.org/10.1107/S0108270103001379

Glidewell, C ; Low, J N ; Skakle, J M S et al. / 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. In: Acta Crystallographica Section C-Crystal Structure Communications. 2003 ; Vol. 59.

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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, INTERPLAY",

author = "C Glidewell and Low, {J N} and Skakle, {J M S} and Wardell, {J L}",

year = "2003",

month = mar,

doi = "10.1107/S0108270103001379",

language = "English",

volume = "59",

journal = "Acta Crystallographica Section C-Crystal Structure Communications",

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publisher = "International Union of Crystallography",

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Glidewell, C, Low, JN, Skakle, JMS & Wardell, JL 2003, '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', Acta Crystallographica Section C-Crystal Structure Communications, vol. 59. https://doi.org/10.1107/S0108270103001379

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. / Glidewell, C ; Low, J N ; Skakle, J M S et al.
In: Acta Crystallographica Section C-Crystal Structure Communications, Vol. 59, 03.2003.

Research output: Contribution to journal › Article › peer-review

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 - 2003/3

Y1 - 2003/3

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 - INTERPLAY

U2 - 10.1107/S0108270103001379

DO - 10.1107/S0108270103001379

M3 - Article

SN - 1600-5759

VL - 59

JO - Acta Crystallographica Section C-Crystal Structure Communications

JF - Acta Crystallographica Section C-Crystal Structure Communications

ER -

Glidewell C, Low JN, Skakle JMS, Wardell JL. 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. Acta Crystallographica Section C-Crystal Structure Communications. 2003 Mar;59. doi: 10.1107/S0108270103001379