The formation of paracetamol (acetaminophen) adducts with hydrogen-bond acceptors

2002 ◽  
Vol 58 (6) ◽  
pp. 1057-1066 ◽  
Author(s):  
Iain D. H. Oswald ◽  
David R. Allan ◽  
Pamela A. McGregor ◽  
W. D. Samuel Motherwell ◽  
Simon Parsons ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Crystal Structures ◽  
Systematic Study ◽  
Guest Molecule ◽  
Guest Molecules ◽  
Oh Groups ◽  
Stacking Interaction ◽  
Hydrogen Bond Interactions ◽  
Π Stacking Interaction ◽  
Graph Set

The crystal structures of five hemiadducts of paracetamol with 1,4-dioxane, N-methylmorpholine, morpholine, N,N-dimethylpiperazine and piperazine and a related 1:1 adduct of paracetamol with 4,4′-bipyridine are described. All structures are characterized by the formation of chains of paracetamol molecules, which are linked via either OH...O=C interactions [C(9) chains in graph-set notation] or NH...O=C interactions [C(4) chains], depending on the presence or absence of substituent groups on the guest molecule. In all cases except for the morpholine and bipyridine adducts these chains are connected by hydrogen-bond interactions with the guest molecules, which reside on crystallographic inversion centres. In the bipyridine adduct this linkage also involves a π-stacking interaction; in the morpholine adduct it is formed between the OH groups of two opposed paracetamol molecules. Most adducts (that with 4,4′-bipyridine is an exception) decompose on heating to give monoclinic paracetamol. This is the first systematic study of a series of co-crystals containing paracetamol.

scholarly journals The crystal structures of three disordered 2-substituted benzimidazole esters

2021 ◽  
Vol 77 (5) ◽  
pp. 473-479
Author(s):  
Chayanna Harish Chinthal ◽  
Hemmige S. Yathirajan ◽  
Nagaraja Manju ◽  
Balakrishna Kalluraya ◽  
Sabine Foro ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Stacking Interaction ◽  
Π Stacking ◽  
Donor And Acceptor ◽  
Π Stacking Interaction ◽  
Related Compounds

The crystal structures of three benzimidazole esters containing aryl or heterocyclic substituents at position 2 are reported, and all three exhibit disorder of molecular entities. In ethyl 1-methyl-2-[4-(prop-2-ynoxy)phenyl]-1H-benzimidazole-5-carboxylate, C20H18N2O3, (I), the prop-2-yn-1-oxyphenyl unit is disordered over two sets of atomic sites having effectively equal occupancies, 0.506 (5) and 0.494 (5). The propyl substituent in ethyl 1-propyl-2-(pyren-1-yl)-1H-benzimidazole-5-carboxylate, C29H24N2O2, (II), is disordered over two sets of atomic sites having occupancies 0.601 (8) and 0.399 (8), and the ester unit in ethyl 1-methyl-2-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1H-benzimidazole-5-carboxylate, C21H19ClN4O2 (III), is disordered over two sets of atomic sites having occupancies 0.645 (7) and 0.355 (7). In each of the C—H...π(arene) hydrogen bonds in (I), the donor and acceptor form parts of different disorder components, so that no continuous aggregation is possible. The molecules of (II) are linked by a single C—H...O hydrogen bond into C(10) chains, which are linked into sheets by a π–π stacking interaction, whereas those of (III) are just linked into C(13) chains, again by a single C—H...O hydrogen bond. Comparisons are made with the structures of some related compounds.

scholarly journals Formation of quinol co-crystals with hydrogen-bond acceptors

2005 ◽  
Vol 61 (1) ◽  
pp. 46-57 ◽  
Author(s):  
Iain D. H. Oswald ◽  
W. D. Samuel Motherwell ◽  
Simon Parsons
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Guest Molecule ◽  
Crystal Packing ◽  
Strong Hydrogen Bond ◽  
Hydrogen Bond Acceptor ◽  
Guest Molecules ◽  
Sterically Hindered

The crystal structures of eight new co-crystals of quinol with pyrazine, piperazine, morpholine, pyridine, piperidine, 4,4′-bipyridine, N-methylmorpholine and N,N′-dimethylpiperazine are reported. Quinol forms 1:1 co-crystals with pyrazine, piperazine and N,N′-dimethylpiperazine, but 1:2 co-crystals with morpholine, 4,4′-bipyridine, N-methylmorpholine, pyridine and piperidine. This difference can be rationalized in most cases by the presence of, respectively, two or one strong hydrogen-bond acceptor(s) in the guest molecule. The exception to this generalization is 4,4′-bipyridine, which forms a 1:2 co-crystal, possibly to optimize crystal packing. All structures are dominated by hydrogen bonding between quinol and the guest molecules. A doubly bridging motif, which connects pairs of quinol and guest molecules via NH...O or CH...O interactions, is present in all but the sterically hindered N,N′-dimethylpiperazine and N-methylmorpholine co-crystals.

scholarly journals Isomers and polymorphs of (E,E)-1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadienes

2006 ◽  
Vol 62 (4) ◽  
pp. 666-675 ◽  
Author(s):  
Christopher Glidewell ◽  
John N. Low ◽  
Janet M. S. Skakle ◽  
James L. Wardell
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Stacking Interactions ◽  
Space Group ◽  
Stacking Interaction ◽  
Space Groups ◽  
Π Stacking ◽  
Π Stacking Interaction ◽  
Polymorphic Forms

The structures of five of the possible six isomers of (E,E)-1,4-bis(nitrophenyl)-2,3-diaza-1,3-butadiene are reported, including two polymorphs of one of the isomers. (E,E)-1,4-Bis(2-nitrophenyl)-2,3-diaza-1,3-butadiene, C14H10N4O4 (I), crystallizes in two polymorphic forms (Ia) and (Ib) in which the molecules lie across centres of inversion in space groups P21/n and P21/c, respectively: the molecules in (Ia) and (Ib) are linked into chains by aromatic π...π stacking interactions and C—H...π(arene) hydrogen bonds, respectively. Molecules of (E,E)-1-(2-nitrophenyl)-4-(3-nitrophenyl)-2,3-diaza-1,3-butadiene (II) are linked into sheets by two independent C—H...O hydrogen bonds. The molecules of (E,E)-1,4-bis(3-nitrophenyl)-2,3-diaza-1,3-butadiene (III) lie across inversion centres in the space group P21/n, and a combination of a C—H...O hydrogen bond and a π...π stacking interaction links the molecules into sheets. A total of four independent C—H...O hydrogen bonds link the molecules of (E,E)-1-(3-nitrophenyl)-4-(4-nitrophenyl)-2,3-diaza-1,3-butadiene (IV) into sheets. In (E,E)-1,4-bis(4-nitrophenyl)-2,3-diaza-1,3-butadiene (V) the molecules, which lie across centres of inversion in the space group P21/n, are linked by just two independent C—H...O hydrogen bonds into a three-dimensional framework.

scholarly journals 1-Benzyl-2-[(2RS,3SR,6SR)-3-methyl-4-oxo-2,6-diphenylpiperidin-1-ylcarbonyl]-2-phenylethenyl phenylacetate

2006 ◽  
Vol 62 (4) ◽  
pp. o1443-o1445
Author(s):  
Kanagasabapathy Thanikasalam ◽  
Ramasubbu Jeyaraman ◽  
Krishnaswamy Panchanatheswaran ◽  
John N. Low ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Title Compound ◽  
Stacking Interaction ◽  
Compound C ◽  
Π Stacking ◽  
Π Stacking Interaction

Molecules of the title compound, C42H37NO4, are weakly linked into chains by a C—H...O hydrogen bond and pairs of such chains are linked by a single aromatic π–π stacking interaction.

scholarly journals Disordered sodium alkoxides from powder data: crystal structures of sodium ethoxide, propoxide, butoxide and pentoxide, and some of their solvates

2021 ◽  
Vol 77 (1) ◽  
pp. 68-82
Author(s):  
Maurice Beske ◽  
Stephanie Cronje ◽  
Martin U. Schmidt ◽  
Lukas Tapmeyer
Keyword(s):  
Hydrogen Bond ◽  
Crystal Structures ◽  
Sodium Ethoxide ◽  
Amyl Alcohol ◽  
X Ray Diffraction ◽  
Oh Groups ◽  
Space Group ◽  
X Ray ◽  
Alkyl Groups ◽  
Hydrogen Bond Networks

The crystal structures of sodium ethoxide (sodium ethanolate, NaOEt), sodium n-propoxide (sodium n-propanolate, NaO n Pr), sodium n-butoxide (sodium n-butanolate, NaO n Bu) and sodium n-pentoxide (sodium n-amylate, NaO n Am) were determined from powder X-ray diffraction data. NaOEt crystallizes in space group P 421 m, with Z = 2, and the other alkoxides crystallize in P4/nmm, with Z = 2. To resolve space-group ambiguities, a Bärnighausen tree was set up, and Rietveld refinements were performed with different models. In all structures, the Na and O atoms form a quadratic net, with the alkyl groups pointing outwards on both sides (anti-PbO type). The alkyl groups are disordered. The disorder becomes even more pronounced with increasing chain length. Recrystallization from the corresponding alcohols yielded four sodium alkoxide solvates: sodium ethoxide ethanol disolvate (NaOEt·2EtOH), sodium n-propoxide n-propanol disolvate (NaO n Pr·2 n PrOH), sodium isopropoxide isopropanol pentasolvate (NaO i Pr·5 i PrOH) and sodium tert-amylate tert-amyl alcohol monosolvate (NaO t Am· t AmOH, t Am = 2-methyl-2-butyl). Their crystal structures were determined by single-crystal X-ray diffraction. All these solvates form chain structures consisting of Na+, –O− and –OH groups, encased by alkyl groups. The hydrogen-bond networks diverge widely among the solvate structures. The hydrogen-bond topology of the i PrOH network in NaO i Pr·5 i PrOH shows branched hydrogen bonds and differs considerably from the networks in pure crystalline i PrOH.

(2RS,4SR)-7-Bromo-2-exo-(2-chlorophenyl)-2,3,4,5-tetrahydro-1,4-epoxynaphtho[1,2-b]azepine: sheets built by the π-stacking of hydrogen-bonded chains

2012 ◽  
Vol 68 (3) ◽  
pp. o123-o125 ◽  
Author(s):  
Andrés F. Yépes ◽  
Alirio Palma ◽  
Justo Cobo ◽  
Christopher Glidewell
Keyword(s):  
Hydrogen Bond ◽  
Title Compound ◽  
Stacking Interaction ◽  
Compound C ◽  
Π Stacking ◽  
Sheet Structure ◽  
Π Stacking Interaction ◽  
Hydrogen Bonded

The molecules of the title compound, C20H15BrClNO, are linked into chains by a C—H...π(arene) hydrogen bond, in which the acceptor is the brominated ring of the naphthalene unit, and these chains are linked by an aromatic π–π stacking interaction, again involving the naphthalene unit, into a sheet structure.

scholarly journals Crystal structures and hydrogen bond analysis of five amino acid conjugates of terephthalic and benzene-1,2,3-tricarboxylic acids

CrystEngComm ◽  
2014 ◽  
Vol 16 (35) ◽  
pp. 8243-8251 ◽  
Author(s):  
Anirban Karmakar ◽  
Clive L. Oliver ◽  
Ana E. Platero-Prats ◽  
Elina Laurila ◽  
Lars Öhrström
Keyword(s):  
Hydrogen Bond ◽  
Amino Acid ◽  
Crystal Structures ◽  
Hirshfeld Surface ◽  
Water Molecules ◽  
Narrow Channels ◽  
Amino Acid Conjugates ◽  
Graph Set ◽  
Hydrogen Bond Analysis ◽  
Hydrogen Bonded

This amino acid derived (red&blue) π-stacked (green) hydrogen bonded (striped) dimer forms a pcu-net with water molecules in the narrow channels. Four related molecules are also presented and all were subjected to graph set and Hirshfeld surface analyses.

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