A Model for Resonance-Assisted Hydrogen Bonding in Crystals and Its Graph Set Analysis

2001 ◽  
Vol 105 (28) ◽  
pp. 6938-6942 ◽  
Author(s):  
Robert W. Munn ◽  
Craig J. Eckhardt
Keyword(s):  
Hydrogen Bonding ◽  
Graph Set ◽  
Graph Set Analysis

Patterns in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals

1995 ◽  
Vol 34 (15) ◽  
pp. 1555-1573 ◽  
Author(s):  
Joel Bernstein ◽  
Raymond E. Davis ◽  
Liat Shimoni ◽  
Ning-Leh Chang
Keyword(s):  
Hydrogen Bonding ◽  
Graph Set ◽  
Graph Set Analysis

The supramolecular architecture of 4-aminoacetophenone (1-(4-fluorophenyl)ethylidene)hydrazone hydrate. Double T-contacts and extremely low-density water layers in a mixed azine

1998 ◽  
Vol 76 (10) ◽  
pp. 1371-1378 ◽  
Author(s):  
Michael Lewis ◽  
Charles L Barnes ◽  
Rainer Glaser
Keyword(s):  
Hydrogen Bonding ◽  
Water Layer ◽  
Low Density ◽  
Supramolecular Architecture ◽  
State Structure ◽  
Supramolecular Synthon ◽  
X Ray ◽  
Water Layers ◽  
Graph Set ◽  
Graph Set Analysis

The crystal structure of unsymmetrical azine 4-aminoacetophenone (1-(4-fluorophenyl)ethylidene)hydrazone hydrate, 1·H2O, was determined. Comparison to the X-ray structures of the symmetrical 4-fluoro- and 4-aminoacetophenone azines, 2 and 3, respectively, reinforces the view of the azine bridge as a conjugation stopper. The focus of the analysis lies with the supramolecular architecture. The structure demonstrates azines as double T-contact synthons and suggests that novel L-type arene-arene contacts also might play a significant role in the supramolecular architecture. The absence of inter-water hydrogen bonding in an extremely low-density water layer is one of the surprising and unique features of the solid-state structure of the title compound. The water layers connect azine layers through a hydrogen bonded network which is described by graph set analysis.Key words: arene-arene interaction, hydrogen bonding, graph set analysis, azine, supramolecular synthon, low density water monolayer.

ChemInform Abstract: Pattern in Hydrogen Bonding: Functionality and Graph Set Analysis in Crystals

ChemInform ◽  
2010 ◽  
Vol 26 (47) ◽  
pp. no-no
Author(s):  
J. BERNSTEIN ◽  
R. E. DAVIS ◽  
L. SHIMONI ◽  
N.-L. CHANG
Keyword(s):  
Hydrogen Bonding ◽  
Graph Set ◽  
Graph Set Analysis

Hydrogen-bonding patterns in the cocrystal 2,4-diamino-6-phenyl-1,3,5-triazine–sorbic acid (1/1)

2007 ◽  
Vol 63 (11) ◽  
pp. o4450-o4451 ◽  
Author(s):  
Kaliyaperumal Thanigaimani ◽  
Packianathan Thomas Muthiah ◽  
Daniel E. Lynch
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Sorbic Acid ◽  
Carboxyl Group ◽  
Amino Group ◽  
Acid Molecule ◽  
Asymmetric Unit ◽  
Graph Set ◽  
Bonding Patterns

In the title cocrystal, C9H9N5·C6H8O2, the asymmetric unit contains one 2,4-diamino-6-phenyl-1,3,5-triazine molecule and a sorbic acid molecule. The triazine molecules are base-paired [with a graph set of R 2 2(8)] on either side via N—H...N hydrogen bonds, forming a supramolecular ribbon along the c axis. Each triazine molecule interacts with the carboxyl group of a sorbic acid molecule via N—H...O and O—H...N hydrogen bonds, generating R 2 2(8) motifs. The supramolecular ribbons are interlinked by N—H...O hydrogen bonds involving the 2-amino group of the triazine molecules and the carboxyl O atom of the sorbic acid molecule.

Supramolecular hydrogen-bonding patterns in two cocrystals of the N(7)–H tautomeric form ofN6-benzoyladenine:N6-benzoyladenine–3-hydroxypyridinium-2-carboxylate (1/1) andN6-benzoyladenine–DL-tartaric acid (1/1)

2015 ◽  
Vol 71 (11) ◽  
pp. 985-990 ◽  
Author(s):  
Ammasai Karthikeyan ◽  
Robert Swinton Darious ◽  
Packianathan Thomas Muthiah ◽  
Franc Perdih
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Tartaric Acid ◽  
Dihedral Angle ◽  
Tautomeric Form ◽  
Stacking Interactions ◽  
Graph Set ◽  
Purine Ring ◽  
Ring Motif

Two novel cocrystals of the N(7)—H tautomeric form ofN6-benzoyladenine (BA), namelyN6-benzoyladenine–3-hydroxypyridinium-2-carboxylate (3HPA) (1/1), C12H9N5O·C6H5NO3, (I), andN6-benzoyladenine–DL-tartaric acid (TA) (1/1), C12H9N5O·C4H6O6, (II), are reported. In both cocrystals, theN6-benzoyladenine molecule exists as the N(7)—H tautomer, and this tautomeric form is stabilized by intramolecular N—H...O hydrogen bonding between the benzoyl C=O group and the N(7)—H hydrogen on the Hoogsteen site of the purine ring, forming anS(7) motif. The dihedral angle between the adenine and phenyl planes is 0.94 (8)° in (I) and 9.77 (8)° in (II). In (I), the Watson–Crick face of BA (N6—H and N1; purine numbering) interacts with the carboxylate and phenol groups of 3HPA through N—H...O and O—H...N hydrogen bonds, generating a ring-motif heterosynthon [graph setR22(6)]. However, in (II), the Hoogsteen face of BA (benzoyl O atom and N7; purine numbering) interacts with TA (hydroxy and carbonyl O atoms) through N—H...O and O—H...O hydrogen bonds, generating a different heterosynthon [graph setR22(4)]. Both crystal structures are further stabilized by π–π stacking interactions.

Polymorphism of urea–barbituric acid co-crystals

2008 ◽  
Vol 64 (5) ◽  
pp. 623-632 ◽  
Author(s):  
Marlena Gryl ◽  
Anna Krawczuk ◽  
Katarzyna Stadnicka
Keyword(s):  
Barbituric Acid ◽  
Spatial Arrangement ◽  
Structural Components ◽  
Space Groups ◽  
The Third ◽  
Tautomeric Forms ◽  
Polymorphic Forms ◽  
Graph Set ◽  
Graph Set Analysis ◽  
Level Analysis

The crystal structures of three polymorphs found for the addition complex of urea and barbituric acid are described and compared. Two polymorphs are monoclinic, space groups P21/c and Cc, whereas the third is triclinic, P\bar 1. The displacement of electron density towards the mesomeric forms, corresponding to the tautomeric forms of higher stability, of the barbituric acid molecule seem to influence the type of hydrogen bonds formed, which in turn determines the different packing topology in the polymorphs. While the polymorphic forms can be easily differentiated at the first-level graph-set analysis of their hydrogen-bonding patterns, a higher-level analysis enables important features of the mutual spatial arrangement of the structural components to be revealed.

scholarly journals Hydrogen-bonding patterns in 2-amino-4,6-dimethoxypyrimidine–4-aminobenzoic acid (1/1)

2006 ◽  
Vol 62 (7) ◽  
pp. o2976-o2978 ◽  
Author(s):  
Kaliyaperumal Thanigaimani ◽  
Packianathan Thomas Muthiah ◽  
Daniel E. Lynch
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Carboxyl Group ◽  
Acid Molecule ◽  
Aminobenzoic Acid ◽  
Graph Set ◽  
Supramolecular Chain ◽  
Bonding Patterns ◽  
Hydrogen Bonded

In the title cocrystal, C6H9N3O2·C7H7NO2, the 2-amino-4,6-dimethoxypyrimidine molecule interacts with the carboxyl group of the 4-aminobenzoic acid molecule through N—H...O and O—H...N hydrogen bonds, forming a cyclic hydrogen-bonded motif [R 2 2(8)]. This motif further self-organizes through N—H...O hydrogen bonds to generate an array of six hydrogen bonds with the rings having the graph-set notation R 2 3(6), R 2 2(8), R 4 2(8), R 2 2(8) and R 2 3(6). The 4-aminobenzoic acid molecules self-assemble via N—H...O hydrogen bonds to form a supramolecular chain along the c axis.

scholarly journals 1H-Pyrazol-2-ium hydrogen oxalate

2012 ◽  
Vol 68 (6) ◽  
pp. o1911-o1911 ◽  
Author(s):  
Chun-Hua Yu ◽  
Run-Qiang Zhu
Keyword(s):  
Hydrogen Bonding ◽  
Title Compound ◽  
Compound C ◽  
Graph Set ◽  
Centrosymmetric Dimers

In the title compound, C3H5N2 +·C2HO4 −, the anions form centrosymmetric dimers through cyclic O—H...O hydrogen-bonding associations [graph set R 2 2(10)]. These dimers are then linked through a cyclic R 4 2(10) N—H...O hydrogen-bonding association involving two cations and the carboxyl O-atom acceptors of separate anions, giving chain structures extending across the (111) plane.

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