Solvent-dependent polymorphism in isomeric N-(nitrobenzylidene)iodoanilines

G  Ferguson; C  Glidewell; J N  Low; J M S  Skakle; J L  Wardell

doi:10.1107/S0108270105016239

Solvent-dependent polymorphism in isomeric N-(nitrobenzylidene)iodoanilines

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

Physics

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

10 Citations (Scopus)

Abstract

Three of the nine isomeric N-(nitrobenzylidene)iodoanilines, C13H9IN2O2, have been found, when crystallized from acetone, to yield polymorphs which differ from those obtained upon crystallization from ethanol. In the second polymorph of 2-iodo-N-(2-nitrobenzylidene)aniline, the molecules are disordered across inversion centres in space group C2/c, but there are no direction-specific interactions between the molecules. In the second polymorph of 2-iodo-N-(3-nitrobenzylidene)aniline, the molecules adopt a different conformation from those in the first polymorph, and they are linked into sheets by a combination of a three-centre iodo-nitro interaction and an aromatic - stacking interaction, both of which are absent from the supramolecular structure of the first polymorph. The second polymorph of 3-iodo-N-(2-nitrobenzylidene)aniline crystallizes with Z' = 2 in space group P21, and the molecules are linked into sheets by one C-HO hydrogen bond and two C-H(arene) hydrogen bonds.

Formula: C52H36I4N8O8, C13H9IN2O2 and C13H9IN2O2

Original language	English
Pages (from-to)	o445-o449
Number of pages	5
Journal	Acta Crystallographica Section C, Crystal Structure Communications
Volume	C61
DOIs	https://doi.org/10.1107/S0108270105016239
Publication status	Published - 2005

Keywords

Pi-stacking interactions
Center-dot-nitro
Crystal-structure prediction
Small organic-molecules
Hydrogen-bonds
Interplay
1,4-diiodobenzene
Patterns

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@article{65ba8e183da0415b8dc2ba48594bf63f,

title = "Solvent-dependent polymorphism in isomeric N-(nitrobenzylidene)iodoanilines",

abstract = "Three of the nine isomeric N-(nitrobenzylidene)iodoanilines, C13H9IN2O2, have been found, when crystallized from acetone, to yield polymorphs which differ from those obtained upon crystallization from ethanol. In the second polymorph of 2-iodo-N-(2-nitrobenzylidene)aniline, the molecules are disordered across inversion centres in space group C2/c, but there are no direction-specific interactions between the molecules. In the second polymorph of 2-iodo-N-(3-nitrobenzylidene)aniline, the molecules adopt a different conformation from those in the first polymorph, and they are linked into sheets by a combination of a three-centre iodo-nitro interaction and an aromatic - stacking interaction, both of which are absent from the supramolecular structure of the first polymorph. The second polymorph of 3-iodo-N-(2-nitrobenzylidene)aniline crystallizes with Z' = 2 in space group P21, and the molecules are linked into sheets by one C-HO hydrogen bond and two C-H(arene) hydrogen bonds. Formula: C52H36I4N8O8, C13H9IN2O2 and C13H9IN2O2 ",

keywords = "Pi-stacking interactions, Center-dot-nitro, Crystal-structure prediction, Small organic-molecules, Hydrogen-bonds, Interplay, 1,4-diiodobenzene, Patterns",

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

year = "2005",

doi = "10.1107/S0108270105016239",

language = "English",

volume = "C61",

pages = "o445--o449",

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

issn = "0108-2701",

publisher = "Wiley-Blackwell ",

}

TY - JOUR

T1 - Solvent-dependent polymorphism in isomeric N-(nitrobenzylidene)iodoanilines

AU - Ferguson, G

AU - Glidewell, C

AU - Low, J N

AU - Skakle, J M S

AU - Wardell, J L

PY - 2005

Y1 - 2005

N2 - Three of the nine isomeric N-(nitrobenzylidene)iodoanilines, C13H9IN2O2, have been found, when crystallized from acetone, to yield polymorphs which differ from those obtained upon crystallization from ethanol. In the second polymorph of 2-iodo-N-(2-nitrobenzylidene)aniline, the molecules are disordered across inversion centres in space group C2/c, but there are no direction-specific interactions between the molecules. In the second polymorph of 2-iodo-N-(3-nitrobenzylidene)aniline, the molecules adopt a different conformation from those in the first polymorph, and they are linked into sheets by a combination of a three-centre iodo-nitro interaction and an aromatic - stacking interaction, both of which are absent from the supramolecular structure of the first polymorph. The second polymorph of 3-iodo-N-(2-nitrobenzylidene)aniline crystallizes with Z' = 2 in space group P21, and the molecules are linked into sheets by one C-HO hydrogen bond and two C-H(arene) hydrogen bonds. Formula: C52H36I4N8O8, C13H9IN2O2 and C13H9IN2O2

AB - Three of the nine isomeric N-(nitrobenzylidene)iodoanilines, C13H9IN2O2, have been found, when crystallized from acetone, to yield polymorphs which differ from those obtained upon crystallization from ethanol. In the second polymorph of 2-iodo-N-(2-nitrobenzylidene)aniline, the molecules are disordered across inversion centres in space group C2/c, but there are no direction-specific interactions between the molecules. In the second polymorph of 2-iodo-N-(3-nitrobenzylidene)aniline, the molecules adopt a different conformation from those in the first polymorph, and they are linked into sheets by a combination of a three-centre iodo-nitro interaction and an aromatic - stacking interaction, both of which are absent from the supramolecular structure of the first polymorph. The second polymorph of 3-iodo-N-(2-nitrobenzylidene)aniline crystallizes with Z' = 2 in space group P21, and the molecules are linked into sheets by one C-HO hydrogen bond and two C-H(arene) hydrogen bonds. Formula: C52H36I4N8O8, C13H9IN2O2 and C13H9IN2O2

KW - Pi-stacking interactions

KW - Center-dot-nitro

KW - Crystal-structure prediction

KW - Small organic-molecules

KW - Hydrogen-bonds

KW - Interplay

KW - 1,4-diiodobenzene

KW - Patterns

U2 - 10.1107/S0108270105016239

DO - 10.1107/S0108270105016239

M3 - Article

SN - 0108-2701

VL - C61

SP - o445-o449

JO - Acta Crystallographica Section C, Crystal Structure Communications

JF - Acta Crystallographica Section C, Crystal Structure Communications

ER -

Solvent-dependent polymorphism in isomeric N-(nitrobenzylidene)iodoanilines

Abstract

Keywords

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