Literature DB >> 19726856

5-Nitro-N4,N6-diphenylpyrimidine-4,6-diamine: polarized molecules linked into pi-stacked chains via three-centre C-H...(O)2 hydrogen bonds.

Ricaurte Rodríguez1, Manuel Nogueras, Justo Cobo, Christopher Glidewell.   

Abstract

Molecules of the title compound, C(16)H(13)N(5)O(2), have no internal symmetry despite the symmetric pattern of substitution in the pyrimidine ring. The intramolecular distances indicate polarization of the electronic structure. There are two intramolecular N-H...O hydrogen bonds and molecules are linked into centrosymmetric dimers by pairs of three-centre C-H...(O)(2) hydrogen bonds. These dimers are linked into chains by means of a pi-pi stacking interaction.

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Year:  2009        PMID: 19726856      PMCID: PMC2737422          DOI: 10.1107/S0108270109029618

Source DB:  PubMed          Journal:  Acta Crystallogr C        ISSN: 0108-2701            Impact factor:   1.172


  11 in total

1.  The Cambridge Structural Database: a quarter of a million crystal structures and rising.

Authors:  Frank H Allen
Journal:  Acta Crystallogr B       Date:  2002-05-29

2.  (E)-3-{2-amino-4-ethoxy-6-[N-(4-methoxyphenyl)-N-methylamino]pyrimidin-5-yl}-1-phenylprop-2-en-1-one: a boat-shaped pyrimidine ring and a chain of hydrogen-bonded R4(2)(8) and R2(2)(20) rings.

Authors:  Jorge Trilleras; Jairo Quiroga; John N Low; Justo Cobo; Christopher Glidewell
Journal:  Acta Crystallogr C       Date:  2007-11-30       Impact factor: 1.172

3.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

4.  A three-dimensional hydrogen-bonded framework in 2-amino-4,6-bis[N-methyl-N-(4-methylphenyl)amino]pyrimidine-5-carbaldehyde and hydrogen-bonded sheets in 2-amino-4-(indolin-1-yl)-6-methoxypyrimidine-5-carbaldehyde.

Authors:  John N Low; Jorge Trilleras; Justo Cobo; Antonio Marchal; Christopher Glidewell
Journal:  Acta Crystallogr C       Date:  2007-10-24       Impact factor: 1.172

5.  Symmetrically 4,6-disubstituted 2-aminopyrimidines and 2-amino-5-nitrosopyrimidines: interplay of molecular, molecular-electronic and supramolecular structures.

Authors:  Antonio Quesada; Antonio Marchal; Manuel Melguizo; John N Low; Christopher Glidewell
Journal:  Acta Crystallogr B       Date:  2004-01-21

6.  N6-substituted 2-amino-4-chloro-5-formylpyrimidines: puckered versus planar pyrimidine rings, and hydrogen-bonded aggregation in zero, one, two and three dimensions.

Authors:  Justo Cobo; Jorge Trilleras; Jairo Quiroga; Antonio Marchal; Manuel Nogueras; John N Low; Christopher Glidewell
Journal:  Acta Crystallogr B       Date:  2008-09-15

7.  2-Amino-4-chloro-5-formyl-6-[methyl(2-methylphenyl)amino]pyrimidine and 2-amino-4-chloro-5-formyl-6-[(2-methoxyphenyl)methylamino]pyrimidine are isostructural and form hydrogen-bonded sheets of R2(2)8 and R6(6)32 rings.

Authors:  Jorge Trilleras; Jairo Quiroga; Justo Cobo; Christopher Glidewell
Journal:  Acta Crystallogr C       Date:  2008-12-13       Impact factor: 1.172

8.  supramolecular structures of N(4)-substituted 2,4-diamino-6-benzyloxy-5-nitrosopyrimidines.

Authors:  Manuel Melguizo; Antonio Quesada; John N Low; Christopher Glidewell
Journal:  Acta Crystallogr B       Date:  2003-03-26

9.  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.

Authors:  Christopher Glidewell; John N Low; Manuel Melguizo; Antonio Quesada
Journal:  Acta Crystallogr C       Date:  2002-12-10       Impact factor: 1.172

10.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
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