N-tert-Butyl-N′-[5-cyano-2-(4-methylphenoxy)phenylsulfonyl]urea, a new TXA2receptor antagonist

2013 ◽  
Vol 69 (8) ◽  
pp. 901-903
Author(s):  
Sylvie-Mireille Bambi-Nyanguile ◽  
Peter Mangwala Kimpende ◽  
Bernard Pirotte ◽  
Luc Van Meervelt
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Crystal Packing ◽  
Theoretical Calculations ◽  
Intramolecular Hydrogen Bonding ◽  
Asymmetric Unit ◽  
Dimer Formation ◽  
Compound C ◽  
Structural Database ◽  
Intramolecular Hydrogen

The title compound, C19H21N3O4S, crystallizes in the space groupP2/cwith two molecules in the asymmetric unit. The conformation of both molecules is very similar and is mainly determined by an intramolecular N—H...O hydrogen bond between a urea N atom and a sulfonyl O atom. The O and second N atom of the urea groups are involved in dimer formationviaN—H...O hydrogen bonds. The intramolecular hydrogen-bonding motif and conformation of the C—SO2—NH(C=O)—NH—C fragment are explored and compared using the Cambridge Structural Database and theoretical calculations. The crystal packing is characterized by π–π stacking between the 5-cyanobenzene rings.

scholarly journals Conformational analysis and intramolecular interactions in monosubstituted phenylboranes and phenylboronic acids

2013 ◽  
Vol 9 ◽  
pp. 1127-1134 ◽  
Author(s):  
Josué M Silla ◽  
Rodrigo A Cormanich ◽  
Roberto Rittner ◽  
Matheus P Freitas
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Conformational Analysis ◽  
Conformational Equilibrium ◽  
Intramolecular Hydrogen Bonding ◽  
Intramolecular Interactions ◽  
Coupling Constant ◽  
Intramolecular Hydrogen ◽  
Phenylboronic Acids ◽  
Electron Donation

A 1 TS J F,H(O) coupling pathway, dictated by a hydrogen bond, in some 2-fluorobenzoic acids has been observed, while such an interaction does not occur in 2-fluorophenol. Thus, this work reports the conformational analysis of 2-fluorophenylboronic acid (1), in order to evaluate a possible intramolecular OH∙∙∙F hydrogen bond in comparison to an nF→pB interaction, which mimics the quantum nF→σ*OH hydrogen bond that would be expected in 2-fluorophenol. 2-Fluorophenylborane (3), which does not experience hydrogen bonding, was used to verify whether nF→pB interaction governs the conformational equilibrium in 1 due to a predominant OH∙∙∙F hydrogen bond or to other effects. A series of 2-X-phenylboranes (X = Cl, Br, NH2, PH2, OH and SH) were further computationally analyzed to search for electron donors to boron, capable of influencing the conformational equilibrium. Overall, the intramolecular OH∙∙∙F hydrogen bond in 1 is quite stabilizing and dictates the 1 h J F,H(O) coupling constant. Moreover, electron donation to the empty p orbital of boron (for noncoplanar BH2 moiety relative to the phenyl ring) is also significantly stabilizing for the NH2 and PH2 derivatives, but not enough to make the corresponding conformers appreciably populated, because of steric effects and the loss of πCC→pB resonance. Thus, the results found earlier for 2-fluorophenol about the lack of intramolecular hydrogen bonding are now corroborated.

scholarly journals Methyl 1-allyl-4-hydroxy-2,2-dioxo-1H-2λ6,1-benzothiazine-3-carboxylate

2013 ◽  
Vol 69 (11) ◽  
pp. o1698-o1698 ◽  
Author(s):  
Svitlana V. Shishkina ◽  
Igor V. Ukrainets ◽  
Lidiya A. Petrushova
Keyword(s):  
Hydrogen Bond ◽  
Asymmetric Unit ◽  
Torsion Angles ◽  
Compound C ◽  
Two Component ◽  
Independent Molecules ◽  
Population Ratio ◽  
Intramolecular Hydrogen ◽  
Vinyl Group ◽  
Planar Fragment

There are two independent molecules in the asymmetric unit of the title compound, C13H13NO5S, in both of which the ester substituent is nearly coplanar [C—C—C—O torsion angles = 2.7 (7) and −0.8 (7)°] with the planar fragment of the bicycle due to the formation of a strong O—H...O intramolecular hydrogen bond. The vinyl group at the ring N atom is approximately orthogonal to the heterocyclic mean plane [C—N—C—C torsion angles = 103.1 (6) and 98.2 (5)°]. The refinement was performed on a two-component, non-merohedrally twinned crystal [population ratio = 0.483 (3):0.517 (3).

scholarly journals (2Z)-2-Bromo-3-[3,5-dibromo-4-(ethylamino)phenyl]-1-(2,4-dichlorophenyl)prop-2-en-1-one

2007 ◽  
Vol 63 (11) ◽  
pp. o4308-o4309 ◽  
Author(s):  
Ray J. Butcher ◽  
Jerry P. Jasinski ◽  
Anil N. Mayekar ◽  
B. Narayana ◽  
H. S. Yathirajan
Keyword(s):  
Hydrogen Bond ◽  
Molecular Conformation ◽  
Crystal Packing ◽  
Phenyl Group ◽  
Hydrogen Bond Interactions ◽  
Compound C ◽  
Propyl Ketone ◽  
Phenyl Rings ◽  
The Mean ◽  
Intramolecular Hydrogen

In the title compound, C17H12Br3Cl2NO, the mean planes of the 3,5-dibromo-4-phenyl and 2,4-dichlorophenyl groups make a dihedral angle of 72.4 (2)°. The dihedral angles between the 2-bromoprop-2-en-1-one group and the two phenyl ring groups (3,5-dibromo-4-phenyl and 2,4-dichlorophenyl) are 71.1 (1) and 10.9 (4)°, respectively. The crystal packing is stabilized by intermolecular N—H...O hydrogen-bond interactions between the ethylamino H atom and the propyl ketone O atom, with the 3,5-dibromo-4-phenyl rings linked in chains in an alternate inverted pattern parallel and oblique to the ac face and diagonally along the a axis of the unit cell. An intramolecular hydrogen bond between the ethyl amino H atom and the 5-Br atom from the 3,5-dibromo-4-phenyl group helps stabilize the molecular conformation.

scholarly journals Relative substituent orientation in the structure ofcis-3-chloro-1,3-dimethyl-N-(4-nitrophenyl)-2-oxocyclopentane-1-carboxamide

2014 ◽  
Vol 70 (9) ◽  
pp. 121-123
Author(s):  
Matthias Zeller ◽  
Jonas Warneke ◽  
Vladimir Azov
Keyword(s):  
Hydrogen Bond ◽  
Crystal Packing ◽  
Membered Ring ◽  
Amide Group ◽  
Aromatic Rings ◽  
Methyl Group ◽  
Compound C ◽  
The Mean ◽  
Graph Set ◽  
Intramolecular Hydrogen

The structure of the title compound, C14H15ClN2O4, prepared by reaction of a methacryloyl dimer with nitroaniline, was determined to establish the relative substituent orientation on the cyclopentanone ring. In agreement with an earlier proposed reaction mechanism, the amide group and the methyl group adjacent to the chloro substituent adopt equatorial positions and relativecisorientation, whereas the Cl substituent itself and the methyl group adjacent to the amide have axial orientations relative to the mean plane of the five-membered ring. The conformation of the molecule is stabilized by one classical N—H...O (2.18 Å) and one non-classical C—H...O (2.23 Å) hydrogen bond, each possessing anS(6) graph-set motif. The crystal packing is defined by several non-classical intramolecular hydrogen bonds, as well as by partial stacking of the aromatic rings.

Theoretical aspects of the enhancement of metal binding affinity by intramolecular hydrogen bonding and modulating pKavalues

2017 ◽  
Vol 41 (24) ◽  
pp. 15110-15119 ◽  
Author(s):  
Ahmad Motahari ◽  
Alireza Fattahi
Keyword(s):  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Binding Affinity ◽  
Metal Binding ◽  
Intramolecular Hydrogen Bonding ◽  
Hydrogen Bond Network ◽  
Bond Network ◽  
The Stability ◽  
Intramolecular Hydrogen

The stability balance shows that the hydrogen bond network and modulation of pKavalues can enhance the metal binding affinity.

scholarly journals Crystal structure and Hirshfeld surface analysis of 4-allyl-2-methoxy-6-nitrophenol

2020 ◽  
Vol 76 (3) ◽  
pp. 461-465
Author(s):  
Yassine El Ghallab ◽  
Sanae Derfoufi ◽  
El Mostafa Ketatni ◽  
Mohamed Saadi ◽  
Lahcen El Ammari
Keyword(s):  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Stacking Interactions ◽  
Asymmetric Unit ◽  
Aromatic Rings ◽  
Compound C ◽  
Independent Molecules ◽  
Intramolecular Hydrogen

The asymmetric unit of the title compound, C10H11NO4, which was synthesized via nitration reaction of eugenol (4-allyl-2-methoxyphenol) with a mixture of nitric acid and sulfuric acid, consists of three independent molecules of similar geometry. Each molecule displays an intramolecular hydrogen bond involving the hydroxide and the nitro group forming an S(6) motif. The crystal cohesion is ensured by intermolecular C—H...O hydrogen bonds in addition to π–π stacking interactions between the aromatic rings [centroid–centroid distances = 3.6583 (17)–4.0624 (16) Å]. The Hirshfeld surface analysis and the two-dimensional fingerprint plots show that H...H (39.6%), O...H/H...O (37.7%), C...H/H...C (12.5%) and C...C (4%) are the most important contributors towards the crystal packing.

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