Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in 2-amino-4,6-dimethoxy-5-nitropyrimidine and pi-stacked hydrogen-bonded sheets in 4-amino-2,6-dimethoxy-5-nitropyrimidine

C  Glidewell; J N  Low; M  Melguizo; A  Quesada

doi:10.1107/S0108270102020322

Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in 2-amino-4,6-dimethoxy-5-nitropyrimidine and pi-stacked hydrogen-bonded sheets in 4-amino-2,6-dimethoxy-5-nitropyrimidine

C Glidewell, J N Low, M Melguizo, A Quesada

School of Chemistry

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

Abstract

In 2-amino-4,6-dimethoxy-5-nitropyrimidine, C6H8N4O4, the molecules are linked by one N-H...N and one N-H...O hydrogen bond to form sheets built from alternating R-2(2) (8) and R-6(6) (32) rings. In isomeric 4-amino-2,6-dimethoxy-5-nitropyrimidine, C6H8N4O4, which crystallizes with Z' = 2 in P (1) over bar, the two independent molecules are linked into a dimer by two independent N-H...N hydrogen bonds. These dimers are linked into sheets by a combination of two-centre C-H...O and three-centre C-H...(O)(2) hydrogen bonds, and the sheets are further linked by two independent aromatic pi-pi-stacking interactions to form a three-dimensional structure.

Original language	English
Number of pages	5
Journal	Acta Crystallographica Section C-Crystal Structure Communications
Volume	59
DOIs	https://doi.org/10.1107/S0108270102020322
Publication status	Published - Jan 2003

Keywords

C-METHYLATED NITROANILINES
3-DIMENSIONAL FRAMEWORK
CRYSTALS

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@article{5247c6b06d3342a882a895b9fe88fbda,

title = "Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in 2-amino-4,6-dimethoxy-5-nitropyrimidine and pi-stacked hydrogen-bonded sheets in 4-amino-2,6-dimethoxy-5-nitropyrimidine",

abstract = "In 2-amino-4,6-dimethoxy-5-nitropyrimidine, C6H8N4O4, the molecules are linked by one N-H...N and one N-H...O hydrogen bond to form sheets built from alternating R-2(2) (8) and R-6(6) (32) rings. In isomeric 4-amino-2,6-dimethoxy-5-nitropyrimidine, C6H8N4O4, which crystallizes with Z' = 2 in P (1) over bar, the two independent molecules are linked into a dimer by two independent N-H...N hydrogen bonds. These dimers are linked into sheets by a combination of two-centre C-H...O and three-centre C-H...(O)(2) hydrogen bonds, and the sheets are further linked by two independent aromatic pi-pi-stacking interactions to form a three-dimensional structure.",

keywords = "C-METHYLATED NITROANILINES, 3-DIMENSIONAL FRAMEWORK, CRYSTALS",

author = "C Glidewell and Low, \{J N\} and M Melguizo and A Quesada",

year = "2003",

month = jan,

doi = "10.1107/S0108270102020322",

language = "English",

volume = "59",

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

issn = "1600-5759",

publisher = "International Union of Crystallography",

}

Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in 2-amino-4,6-dimethoxy-5-nitropyrimidine and pi-stacked hydrogen-bonded sheets in 4-amino-2,6-dimethoxy-5-nitropyrimidine. / Glidewell, C ; Low, J N ; Melguizo, M et al.
In: Acta Crystallographica Section C-Crystal Structure Communications, Vol. 59, 01.2003.

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

TY - JOUR

T1 - Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in 2-amino-4,6-dimethoxy-5-nitropyrimidine and pi-stacked hydrogen-bonded sheets in 4-amino-2,6-dimethoxy-5-nitropyrimidine

AU - Glidewell, C

AU - Low, J N

AU - Melguizo, M

AU - Quesada, A

PY - 2003/1

Y1 - 2003/1

N2 - In 2-amino-4,6-dimethoxy-5-nitropyrimidine, C6H8N4O4, the molecules are linked by one N-H...N and one N-H...O hydrogen bond to form sheets built from alternating R-2(2) (8) and R-6(6) (32) rings. In isomeric 4-amino-2,6-dimethoxy-5-nitropyrimidine, C6H8N4O4, which crystallizes with Z' = 2 in P (1) over bar, the two independent molecules are linked into a dimer by two independent N-H...N hydrogen bonds. These dimers are linked into sheets by a combination of two-centre C-H...O and three-centre C-H...(O)(2) hydrogen bonds, and the sheets are further linked by two independent aromatic pi-pi-stacking interactions to form a three-dimensional structure.

AB - In 2-amino-4,6-dimethoxy-5-nitropyrimidine, C6H8N4O4, the molecules are linked by one N-H...N and one N-H...O hydrogen bond to form sheets built from alternating R-2(2) (8) and R-6(6) (32) rings. In isomeric 4-amino-2,6-dimethoxy-5-nitropyrimidine, C6H8N4O4, which crystallizes with Z' = 2 in P (1) over bar, the two independent molecules are linked into a dimer by two independent N-H...N hydrogen bonds. These dimers are linked into sheets by a combination of two-centre C-H...O and three-centre C-H...(O)(2) hydrogen bonds, and the sheets are further linked by two independent aromatic pi-pi-stacking interactions to form a three-dimensional structure.

KW - C-METHYLATED NITROANILINES

KW - 3-DIMENSIONAL FRAMEWORK

KW - CRYSTALS

UR - https://www.scopus.com/pages/publications/0037254992

U2 - 10.1107/S0108270102020322

DO - 10.1107/S0108270102020322

M3 - Article

SN - 1600-5759

SN - 0108-2701

VL - 59

JO - Acta Crystallographica Section C-Crystal Structure Communications

JF - Acta Crystallographica Section C-Crystal Structure Communications

ER -

Hydrogen bonding in nitroaniline analogues: hydrogen-bonded sheets in 2-amino-4,6-dimethoxy-5-nitropyrimidine and pi-stacked hydrogen-bonded sheets in 4-amino-2,6-dimethoxy-5-nitropyrimidine

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