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32 results on '"Abdelwahed Auhmani"'

1. Crystal structure of (R)-5-[(R)-3-(4-chlorophenyl)-5-methyl-4,5-dihydroisoxazol-5-yl]-2-methylcyclohex-2-enone

Author

Ali Oubella, My Youssef Ait Itto, Aziz Auhmani, Abdelkhalek Riahi, Jean-Claude Daran, and Abdelwahed Auhmani

Subjects
isoxazole derivatives, absolute configuration, natural products, pharmaceutical activities, crystal structure, Crystallography, QD901-999
Abstract

The title compound, C17H18ClNO2, was prepared and isolated as a pure diastereoisomer, using column chromatography followed by a succession of fractional crystallizations. Its exact structure was fully identified via 1H NMR and confirmed by X-ray diffraction. It is built up from a central five-membered dihydroisoxazole ring to which a p-chlorophenyl group and a cyclohex-2-enone ring are attached in the 3 and 5 positions. The cyclohex-2-one and isoxazoline rings each exhibit an envelope conformation. The crystal packing features C—H...O, C—H...N and C—H...π interactions, which generate a three-dimensional network.

Published
2020
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2. Crystal structure of 2-isopropyl-4-methoxy-5-methylphenyl 4-methylbenzenesulfonate

Author

Yassine Laamari, Aziz Auhmani, My Youssef Ait Itto, Jean-Claude Daran, Abdelwahed Auhmani, and Mostafa Kouili

Subjects
crystal structure, organic synthesis, tosylation of alcohols, drug synthesis, Crystallography, QD901-999
Abstract

The title compound, C18H22O4S, an hemisynthetic product, was obtained by the tosylation reaction of the naturally occurring meroterpene p-methoxythymol. The molecule comprises a tetrasubstitued phenyl ring linked to a toluenesulfonate through one of its O atoms. In the crystal, C—H...O and C—H...π interactions link the molecules, forming a three-dimensional network.

Published
2018
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3. Crystal structure of dimethyl 2-((2Z,5Z)-5-(2-methoxy-2-oxoethylidene)-2-{(E)-[2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene]hydrazinylidene}-4-oxothiazolidin-3-yl)fumarate

Author

Abdellah N'ait Ousidi, My Youssef Ait Itto, Aziz Auhmani, Abdelkhalek Riahi, Abdelwahed Auhmani, and Jean-Claude Daran

Subjects
crystal structure, heterocyclic compounds, thiazolidine derivatives, natural product, Crystallography, QD901-999
Abstract

The crystal structure and the conformation of the title compound, C22H27N3O7S, were determined from the synthetic pathway and by X-ray analysis. This compound is a new 4-thiazolidinone derivative prepared and isolated as pure product from thiosemicarbazone carvone. The molecule is built up from an oxothiazolidine ring tetrasubstituted by a methoxy–oxoethylidene, a maleate, an oxygen and a cyclohexylidene–hydrazone. The cyclohexylidene ring is statistically disordered over two positions, resulting in an inversion of configuration for the substituted carbon.

Published
2017
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4. Crystal structure of (1S,3R,8R,9R)-2,2-dichloro-3,7,7-trimethyl-10-methylenetricyclo[6.4.0.01,3]dodecan-9-ol

Author

Ahmed Benzalim, Aziz Auhmani, Abdoullah Bimoussa, My Youssef Ait Itto, Jean-Claude Daran, and Abdelwahed Auhmani

Subjects
crystal structure, absolute configuration, sesquiterpenes, asymmetric synthesis, natural products, Crystallography, QD901-999
Abstract

The title compound, C16H24Cl2O, was synthesized by treating (1S,3R,8S,9R,10S)-2,2-dichloro-3,7,7,10-tetramethyl-9,10-epoxytricyclo[6.4.0.01,3]dodecane with a concentrated solution of hydrobromic acid. It is built up from three fused rings: a cycloheptane ring, a cyclohexyl ring bearing alkene and hydroxy substituents, and a cyclopropane ring bearing two chlorine atoms. The asymmetric unit contains two molecules linked by an O—H...O hydrogen bond. In the crystal, further O—H...O hydrogen bonds build up an R44(8) cyclic tetramer. One of the molecules presents disorder that affects the seven-membered ring. In both molecules, the six-membered rings display a chair conformation, whereas the seven-membered rings display conformations intermediate between boat and twist-boat for the non-disordered molecule and either a chair or boat and twist-boat for the disordered molecule owing to the disorder. The absolute configuration for both molecules is 1S,3R,8R,9R and was deduced from the chemical pathway and further confirmed by the X-ray structural analysis.

Published
2016
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5. (1S,3R,8R,11S)-2,2,11-Tribromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

Author

Abdoullah Bimoussa, Aziz Auhmani, My Youssef Ait Itto, Jean-Claude Daran, and Abdelwahed Auhmani

Subjects
crystal structure, absolute configuration, sesquiterpene, asymmetric synthesis, natural products, Crystallography, QD901-999
Abstract

The title compound, C16H22Br4, was synthesized in two steps from β-himachalene, which was isolated from essential oil of the Atlas cedar (cedrus atlantica). It is built up from three fused rings, a seven-membered heptane ring, a six-membered cyclohexyl ring bearing both a bromine and a bromomethyl substituent, and a three-membered propane ring bearing two Br atoms. In the crystal, molecules are linked by C—H...Br hydrogen bonds, forming chains propagating along [001]. The absolute configuration was deduced from the chemical pathway and confirmed by resonant scattering [Flack parameter = 0.012 (10)].

Published
2016
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6. Crystal structure of (1R,3S,8R,11R)-11-acetyl-3,7,7-trimethyl-10-oxatricyclo[6.4.0.01,3]dodecan-9-one

Author

Abdoullah Bismoussa, My Youssef Ait Itto, Jean-Claude Daran, Abdelwahed Auhmani, and Aziz Auhmani

Subjects
Lactones, fused rings, biological activities, crystal structure, Crystallography, QD901-999
Abstract

The title compound, C16H24O3, is built up from three fused rings, a six-membered, a seven-membered and a three-membered ring. The absolute configuration of the title compound was determined as (1R,3S,8R,11R) based on the synthetic pathway. The six-membered ring has an half-chair conformation whereas the seven-membered ring displays a boat conformation. In the cyrstal, C—H...O hydrogen bonds build up a two-dimensional network parallel to (0 0 1). The crystal studied was an inversion twin with a minor twin component of 34%.

Published
2015
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7. Crystal structure of (1R,2S,4R,7R,8S,9R)-3,3-dichloro-8,9-epoxy-4,8,12,12-tetramethyltricyclo[5.5.0.02,4]dodecane

Author

Ahmed Benzalim, Aziz Auhmani, My Youssef Ait Itto, Jean-Claude Daran, and Abdelwahed Auhmani

Subjects
crystal structure, absolute configuration, natural products, epoxide, Crystallography, QD901-999
Abstract

The title compound, C16H24Cl2O, is built up from two fused six- and seven-membered rings which bear a dichlorocyclopropane group and an epoxy group, respectively. In the molecule, the six-membered ring adopts an envelope configuration with the C atom linking the epoxy ring at the flap, while the seven-membered ring adopts a boat–sofa conformation.

Published
2015
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8. (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl benzoate

Author

Radouane Oubabi, Aziz Auhmani, My Youssef Ait Itto, Abdelwahed Auhmani, and Jean-Claude Daran

Subjects
crystal structure, Crystallography, QD901-999
Abstract

The title compound, C27H34O2, was hemisynthesized through direct benzoylation of the naturally occurring meroterpene totarol. The central fused six-membered ring has a half-chair conformation, whereas the terminal six-membered ring displays a chair conformation. The dihedral angle between the fused benzene ring and the benzoyl benzene ring is 73.05 (14)°. The S,S chirality of the molecule is consistent with the synthetic pathway, and confirmed by the refinement of the Flack parameter.

Published
2014
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9. (1S,3S,8R,9S,10R)-9,10-Epoxy-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodecane

Author

Abdoullah Bimoussa, Aziz Auhmani, My Youssef Ait Itto, Jean-Claude Daran, and Abdelwahed Auhmani

Subjects
Crystallography, QD901-999
Abstract

The title compound, C16H26O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-9-ene with metachloroperbenzoic acid. The molecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present.

Published
2014
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10. (4bS,8aS)-1-Isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl acetate

Author

Radouane Oubabi, Aziz Auhmani, My Youssef Ait Itto, Abdelwahed Auhmani, and Jean-Claude Daran

Subjects
Crystallography, QD901-999
Abstract

The hemisynthesis of the title compound, C22H32O2, was carried out through direct acetylation reaction of the naturally occurring diterpene totarol [systematic name: (4bS,8aS)-4b,8,8-trimethyl-1-propan-2-yl-5,6,7,8a,9,10-hexahydrophenanthren-2-ol]. The molecule is built up from three fused six membered rings, one saturated and two unsaturated. The central unsaturated ring has a half-chair conformation, whereas the other unsaturated ring displays a chair conformation. The absolute configuration is deduced from the chemical pathway. The value of the Hooft parameter [−0.10 (6)] allowed this absolute configuration to be confirmed.

Published
2014
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11. Absolute configuration of (1S,3R,8R)-10-bromomethyl-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

Author

Abdoullah Bimoussa, Aziz Auhmani, My Youssef Ait Itto, Jean-Claude Daran, and Abdelwahed Auhmani

Subjects
Crystallography, QD901-999
Abstract

The absolute configuration of the title compound, C16H23BrCl2, has been deduced from the chemical pathway and fully confirmed by refinement of the Flack and Hooft parameters. The six-membered ring adopts a half-chair conformation, whereas the seven-membered ring is a twisted chair. The molecular packing within the crystal is stabilized only by van der Waals interactions.

Published
2013
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12. Crystal structure of (

Author

Ali, Oubella, My Youssef, Ait Itto, Aziz, Auhmani, Abdelkhalek, Riahi, Jean-Claude, Daran, and Abdelwahed, Auhmani

Subjects
absolute configuration, crystal structure, natural products, pharmaceutical activities, isoxazole derivatives, Research Communications
Abstract

The title compound is a pure diastereoisomer built up from a central five-membered di­hydro­isoxazole ring substituted in the 3 and 5 positions by a p-chloro­phenyl group and a cyclo­hex-2-enone ring. The cyclo­hex-2-one and the isoxazoline rings both exhibit an envelope conformation. The crystal packing features C—H⋯O, C—H⋯N and C—H⋯π inter­actions., The title compound, C17H18ClNO2, was prepared and isolated as a pure diastereoisomer, using column chromatography followed by a succession of fractional crystallizations. Its exact structure was fully identified via 1H NMR and confirmed by X-ray diffraction. It is built up from a central five-membered di­hydro­isoxazole ring to which a p-chloro­phenyl group and a cyclo­hex-2-enone ring are attached in the 3 and 5 positions. The cyclo­hex-2-one and isoxazoline rings each exhibit an envelope conformation. The crystal packing features C—H⋯O, C—H⋯N and C—H⋯π inter­actions, which generate a three-dimensional network.

Published
2020

13. Synthesis, crystal structure, DFT studies and Hirshfeld surface analysis of novel isoxazole derivatives

Author

El Mostafa Ketatni, Lahcen El Ammari, Abdelwahed Auhmani, My Youssef Ait Itto, Mostafa Khouili, Aziz Auhmani, Mohamed Saadi, and Yassine Laamari

Subjects
010405 organic chemistry, Hydrogen bond, Organic Chemistry, Intermolecular force, Supramolecular chemistry, Crystal structure, 010402 general chemistry, 01 natural sciences, Cycloaddition, 0104 chemical sciences, Analytical Chemistry, Inorganic Chemistry, Crystal, chemistry.chemical_compound, Crystallography, chemistry, Molecular orbital, Isoxazole, Spectroscopy
Abstract

This article describes firstly the synthesis of a new series of isoxazole 5a-e from p-methoxythymol, extracted from Tetraclinis Articulata, as starting material involving 1,3-dipolar cycloaddition reaction and secondly a detailed study of the molecular packing and intermolecular interactions in crystals of five related 5-((2-isopropyl-4-‑methoxy‑5-methylphenoxy)methyl)-3-phenylisoxazole derivatives. All compounds were synthesized and subjected to solid state characterization by single-crystal X-ray diffraction analysis, and to studies with the use of NMR and Hirshfeld surface analysis. All structures display intermolecular C—H···O hydrogen bonding and C—H···π interactions, forming layers in the crystal lattice. The crystal structures of compounds 5a; 5c and 5d are consolidated by π—π interactions. Hirshfeld surface analysis, the dnorm surfaces, electrostatic potential and two-dimensional fingerprint plots were examined to verify the contributions of the different intermolecular contacts within the supramolecular structure. The most important contributions for the crystal packing are from H···H, H···C/C···H and O···H/H···O interactions. Additionally, DFT calculations have been used to analyze the electronic and geometric frontier molecular orbital and Molecular Electrostatic Potential map analyses of the compounds were produced using the optimized structures.

Published
2021
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14. Hemisynthesis, crystal structure and inhibitory effect of sesquiterpenic thiosemicarbazones and thiazolidin-4-ones on the corrosion behaviour of stainless steel in 1 M H2SO4 solution

Author

A. Abouelfida, Moulay Youssef Ait Itto, Abdelaziz Benyaich, Olivier Mentré, Aziz Auhmani, Abdelwahed Auhmani, Abdoullah Bimoussa, El Mostafa Ketatni, Yassine Koumya, Unité de Catalyse et Chimie du Solide - UMR 8181 (UCCS), Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille, Centrale Lille Institut (CLIL)-Université d'Artois (UA)-Centrale Lille-Centre National de la Recherche Scientifique (CNRS)-Institut de Chimie du CNRS (INC)-Université de Lille, and Université d'Artois (UA)-Centrale Lille-Institut de Chimie du CNRS (INC)-Université de Lille-Centre National de la Recherche Scientifique (CNRS)

Subjects
crystal structure, Band gap, Cyclohexane conformation, C-HÁ Á ÁCl hydrogen bonding, Crystal structure, sesquiterpene hydrocarbon, [CHIM.INOR]Chemical Sciences/Inorganic chemistry, 010402 general chemistry, 010403 inorganic & nuclear chemistry, 01 natural sciences, thiazolidinone, DFT, essential oil, Inorganic Chemistry, chemistry.chemical_compound, thiosemicarbazone, Materials Chemistry, [CHIM]Chemical Sciences, Physical and Theoretical Chemistry, Semicarbazone, ComputingMilieux_MISCELLANEOUS, polarization, corrosion, Hydrogen bond, Absolute configuration, Condensed Matter Physics, computational chemistry, cyclic voltammetry, 0104 chemical sciences, Crystallography, hemisynthesis, chemistry, Flack parameter, Cyclic voltammetry
Abstract

Treatment of thiosemicarbazones prepared from sesquiterpenes with ethyl 2-bromoacetate in the presence of sodium acetate afforded the corresponding thiazolidin-4-ones. The structures of all the newly synthesized compounds were established by considering spectral and single-crystal X-ray diffraction data. The title compound, ethyl 2-((Z)-2-{(Z)-[(1aR,5aR,9aS)-1,1-dichloro-1a,5,5,7-tetramethyl-1a,2,3,4,5,5a,8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-8-ylidene]hydrazono}-4-oxothiazolidin-3-yl)acetate, C23H31Cl2N3O3S, 5, crystallizes in the orthorhombic noncentrosymmetric space group P212121 with Z = 4. Within the molecule in the crystal structure, the cyclohexene ring has an envelope conformation and the cycloheptane ring, to which it is fused, has a boat conformation. In the crystal, molecules are linked by C—H...Cl hydrogen bonds forming chains propagating along the b-axis direction. The absolute configuration of the molecule in the crystal could be fully confirmed from anomalous dispersion effects [Flack parameter = −0.04 (2)]. Thiosemicarbazones 1 and 2 are efficient inhibitors for steel corrosion in 1 M H2SO4 solution, with a maximum efficiency of 92.28% at 10−3 M. Furthermore, thiosemicarbazone compounds were found to be more efficient than thiazolidin-4-one derivatives. In addition, cyclic voltammetry was used to characterize the tested molecules, as well to estimate the experimental value of the energy band gap.

Published
2019
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15. New polysubstituted monoterpenic thiazolidinones: synthesis, spectroscopic and crystal structure studies

Author

Abdellah N'ait Ousidi, Aziz Auhmani, Abdelwahed Auhmani, Moulay Youssef Ait Itto, Abdelkhalek Riahi, Anthony Robert, Jean Claude Daran, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
010405 organic chemistry, Hydrogen bond, Chemistry, Crystal structure, Absolute configuration, Nuclear magnetic resonance spectroscopy, 010402 general chemistry, Condensed Matter Physics, 01 natural sciences, 0104 chemical sciences, Inorganic Chemistry, Crystallography, Synthesis, Thiazolidine derivatives, Materials Chemistry, Molecule, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Physical and Theoretical Chemistry, Monoterpenic compounds
Abstract

The synthesis of three new polysubstituted monoterpenic thiazolidin-4-ones, namely (Z)-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C14H21N3OS (2), (2Z,5Z)-5-[(dimethylamino)methylidene]-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C16H24N4OS (3), and (2Z,5Z)-5-[(dimethylamino)methylidene]-3-methyl-2-{(E)-[(1R,4R)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ylidene]hydrazinylidene}thiazolidin-4-one, C17H26N4OS (4), is reported, starting from the corresponding thiosemicarbazones obtained from naturally occurring (R)-camphor. All the newly obtained thiazolidin-4-ones have been fully characterized by HRMS and 1H and 13C (1D and 2D) NMR spectroscopy. Two of them, i.e. 2 and 3, were identified by single-crystal X-ray crystallography, confirming the synthetic pathway and the spectroscopic analyses. In 3, there are two roughly identical molecules within the asymmetric unit with the same absolute configuration. These two molecules are linked through N—H...O hydrogen bonds, building an R 2 2(8) graph-set motif.

Published
2018
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16. Hemisynthesis, crystal structure and inhibitory effect of sesquiterpenic thiosemicarbazones and thiazolidin-4-ones on the corrosion behaviour of stainless steel in 1 M H

Author

Abdoullah, Bimoussa, Yassine, Koumya, Abdesselam, Abouelfida, Moulay Youssef, Ait Itto, Abdelaziz, Benyaich, Olivier, Mentre, El Mostafa, Ketatni, Aziz, Auhmani, and Abdelwahed, Auhmani

Abstract

Treatment of thiosemicarbazones prepared from sesquiterpenes with ethyl 2-bromoacetate in the presence of sodium acetate afforded the corresponding thiazolidin-4-ones. The structures of all the newly synthesized compounds were established by considering spectral and single-crystal X-ray diffraction data. The title compound, ethyl 2-((Z)-2-{(Z)-[(1aR,5aR,9aS)-1,1-dichloro-1a,5,5,7-tetramethyl-1a,2,3,4,5,5a,8,9-octahydro-1H-benzo[a]cyclopropa[b][7]annulen-8-ylidene]hydrazono}-4-oxothiazolidin-3-yl)acetate, C

Published
2018

17. Crystal structure of 2-isopropyl-4-methoxy-5-methylphenyl 4-methylbenzenesulfonate

Author

Aziz Auhmani, Jean-Claude Daran, Mostafa Kouili, Abdelwahed Auhmani, My Youssef Ait Itto, Yassine Laamari, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), and Université Sultan Moulay Slimane (USMS )

Subjects
tosyl­ation of alcohols, Organic synthesis, Crystal structure, 010402 general chemistry, 010403 inorganic & nuclear chemistry, Ring (chemistry), 01 natural sciences, Medicinal chemistry, Research Communications, Crystal, chemistry.chemical_compound, Drug synthesis, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Tosylation of alcohols, Meroterpene, Crystallography, General Chemistry, Meth, Condensed Matter Physics, 3. Good health, 0104 chemical sciences, Sulfonate, chemistry, QD901-999, Isopropyl
Abstract

The title compound, an hemisynthetic product, was obtained by the tosyl­ation reaction of the naturally occurring meroterpene p-meth­oxy­thymol 1., The title compound, C18H22O4S, an hemisynthetic product, was obtained by the tosyl­ation reaction of the naturally occurring meroterpene p-meth­oxy­thymol. The mol­ecule comprises a tetra­substitued phenyl ring linked to a toluene­sulfonate through one of its O atoms. In the crystal, C—H⋯O and C—H⋯π inter­actions link the mol­ecules, forming a three-dimensional network.

Published
2018
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18. Crystal structure of dimethyl 2-((2 Z ,5 Z )-5-(2-methoxy-2-oxoethylidene)-2-{( E )-[2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enylidene]hydrazinylidene}-4-oxothiazolidin-3-yl)fumarate

Author

Abdelwahed Auhmani, Aziz Auhmani, Abdellah N'ait Ousidi, Jean-Claude Daran, Abdelkhalek Riahi, My Youssef Ait Itto, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Stereochemistry, Hydrazone, Crystal structure, 010403 inorganic & nuclear chemistry, Ring (chemistry), 01 natural sciences, Natural product, Research Communications, lcsh:Chemistry, chemistry.chemical_compound, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, chemistry.chemical_classification, 010405 organic chemistry, General Chemistry, Meth, Condensed Matter Physics, 3. Good health, 0104 chemical sciences, Thiazolidine derivatives, chemistry, lcsh:QD1-999, thia­zolidine derivatives, Heterocyclic compounds, Derivative (chemistry)
Abstract

The crystal structure of the title compound, dimethyl 2-((2Z,5Z)-5-(2-meth­oxy-2-oxo­ethyl­idene)-2-{(E)-[2-methyl-5-(prop-1-en-2-yl)cyclo­hex-2-enyl­idene]hydrazinyl­idene}-4-oxo­thia­zolidin-3-yl)fumarate displays a conformational disorder which inverts the configuration of the chiral C atom within the cyclo­hexyl­idene ring., The crystal structure and the conformation of the title compound, C22H27N3O7S, were determined from the synthetic pathway and by X-ray analysis. This compound is a new 4-thia­zolidinone derivative prepared and isolated as pure product from thio­semicarbazone carvone. The mol­ecule is built up from an oxo­thia­zolidine ring tetra­substituted by a meth­oxy–oxo­ethyl­idene, a maleate, an oxygen and a cyclo­hexyl­idene–hydrazone. The cyclo­hexyl­idene ring is statistically disordered over two positions, resulting in an inversion of configuration for the substituted carbon.

Published
2017
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19. (1S,3R,8R,11S)-2,2,11-Tribromo-10-bromomethyl-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

Author

Abdelwahed Auhmani, Jean-Claude Daran, Abdoullah Bimoussa, Aziz Auhmani, My Youssef Ait Itto, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Sesquiterpene, Stereochemistry, Substituent, chemistry.chemical_element, Crystal structure, 010402 general chemistry, 010403 inorganic & nuclear chemistry, 01 natural sciences, chemistry.chemical_compound, lcsh:QD901-999, Absolute configuration, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Ene reaction, Natural products, Heptane, Bromine, Chemistry, Hydrogen bond, Asymmetric synthesis, General Medicine, 0104 chemical sciences, Crystallography, lcsh:Crystallography, Flack parameter
Abstract

The title compound, C16H22Br4, was synthesized in two steps from β-himachalene, which was isolated from essential oil of the Atlas cedar (cedrus atlantica). It is built up from three fused rings, a seven-membered heptane ring, a six-membered cyclohexyl ring bearing both a bromine and a bromomethyl substituent, and a three-membered propane ring bearing two Br atoms. In the crystal, molecules are linked by C—H...Br hydrogen bonds, forming chains propagating along [001]. The absolute configuration was deduced from the chemical pathway and confirmed by resonant scattering [Flack parameter = 0.012 (10)].

Published
2016
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20. (3a R ,6 R )-3,3,6-Trimethyl-3,3a,4,5,6,7-hexahydro-2 H -indazole-2-carbothioamide

Author

Abdelwahed Auhmani, M. Berraho, Abdelkhalek Riahi, M.Y. Ait Itto, A. N’Ait Ousidi, Sylviane Chevreux, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Institut de Chimie Moléculaire de Reims - UMR 7312 (ICMR), SFR Condorcet, Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Centre National de la Recherche Scientifique (CNRS)-SFR CAP Santé (Champagne-Ardenne Picardie Santé), and Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Université de Picardie Jules Verne (UPJV)-Université de Reims Champagne-Ardenne (URCA)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
crystal structure, Stereochemistry, N—H...N hydrogen bonds, Cyclohexane conformation, Thio, Dihedral angle, thiosemicarbazide, 010403 inorganic & nuclear chemistry, Ring (chemistry), 01 natural sciences, N-HS hydrogen bonds, thio­semicarbazide, chemistry.chemical_compound, Amide, lcsh:QD901-999, [CHIM]Chemical Sciences, N—H...S hydrogen bonds, Indazole, 010405 organic chemistry, Hydrogen bond, [CHIM.ORGA]Chemical Sciences/Organic chemistry, carbo­thio­amide, General Medicine, HEXA, 3. Good health, 0104 chemical sciences, Crystallography, N-HN hydrogen bonds, chemistry, carbothioamide, indazole, lcsh:Crystallography
Abstract

The title compound, C11H19N3S, was prepared by the reaction of (R)-pulegone with thiosemicarbazide in acidic medium, using ethanol as solvent. The molecule is built up from fused six and five-membered rings. The six-membered ring adopts a chair conformation, while the five-membered ring displays an envelope conformation with the dimethyl-substituted C atom as the flap. The dihedral angle between the mean planes of the two rings is 20.35 (6)°. In the crystal, molecules are linked by N—H...N and N—H...S hydrogen bonds into chains running parallel to [100].

Published
2016
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21. Crystal structure of (1S,3R,8R,10S)-2,2-dichloro-10-hydroxy-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodecan-9-one

Author

M.Y. Ait Itto, Auhmani Abdelwahed, Jean-Claude Daran, Abdelwahed Auhmani, A. Benzalim, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
crystal structure, Ketone, natural products, Stereochemistry, Dimer, asymmetric synthesis, Crystal structure, 010402 general chemistry, Ring (chemistry), 01 natural sciences, Research Communications, lcsh:Chemistry, chemistry.chemical_compound, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, chemistry.chemical_classification, 010405 organic chemistry, Hydrogen bond, α-hy­droxy­ketone, Absolute configuration, Enantioselective synthesis, General Chemistry, hydrogen bonding, Condensed Matter Physics, 3. Good health, 0104 chemical sciences, absolute configuration, lcsh:QD1-999, chemistry, Flack parameter, α-hydroxyketone
Abstract

The asymmetric unit of title compound contains two independent mol­ecules which are built from three fused rings: a heptane ring, a cyclo­hexyl ring bearing a ketone and an alcohol group, and a three-membered cyclo­propane ring bearing two Cl atoms. In the crystal, the mol­ecules are linked by O—H⋯O and C—H⋯O hydrogen bonds, forming chains propagating along [100]., The asymmetric unit of the title compound, C16H24Cl2O2, contains two independent mol­ecules (A and B) which are built from three fused rings, viz. a seven-membered heptane ring, a six-membered cyclo­hexyl ring bearing a ketone and an alcohol group, and a cyclo­propane ring bearing two Cl atoms. In the crystal, the two mol­ecules are linked via two O—H⋯O hydrogen bonds, forming an A–B dimer with an R 2 2(10) ring motif. The A mol­ecules of these dimers are linked via a C—H⋯O hydrogen bond, forming chains propagating along the a-axis direction. Both mol­ecules have the same absolute configuration, i.e. 1S,3R,8R,10S, which is based on the synthetic pathway and further confirmed by resonant scattering [Flack parameter = 0.03 (5)].

Published
2016
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22. (1S,3S,8R,9S,10R)-9,10-Ep-oxy-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodeca-ne

Author

Aziz Auhmani, Abdoullah Bimoussa, My Youssef Ait Itto, Jean-Claude Daran, Abdelwahed Auhmani, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
biology, Chemistry, Cyclohexane conformation, Intermolecular force, General Chemistry, Condensed Matter Physics, Bioinformatics, biology.organism_classification, Ring (chemistry), Organic Papers, 3. Good health, Crystal, lcsh:Chemistry, Crystallography, lcsh:QD1-999, Tetra, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry
Abstract

The title compound, C16H26O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetramethyltricyclo[6.4.0.01,3]dodec-9-ene with metachloroperbenzoic acid. The molecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present.

Published
2014
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24. (4bS,8aS)-1-isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octahydrophenanthren-2-yl benzoate

Author

Jean-Claude Daran, Abdelwahed Auhmani, My Youssef Ait Itto, Aziz Auhmani, Radouane Oubabi, Laboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Faculté des Sciences Semlalia Marrakech, Laboratoire de chimie de coordination (LCC), Institut National Polytechnique (Toulouse) (Toulouse INP), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Université Toulouse III - Paul Sabatier (UT3), Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie de Toulouse (ICT-FR 2599), Université Fédérale Toulouse Midi-Pyrénées-Université Fédérale Toulouse Midi-Pyrénées-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Université Toulouse III - Paul Sabatier (UT3), and Université Fédérale Toulouse Midi-Pyrénées-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Institut de Recherche pour le Développement (IRD)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)

Subjects
Meroterpene, crystal structure, Crystallography, 010405 organic chemistry, Chemistry, Totarol, Cyclohexane conformation, General Chemistry, Dihedral angle, 010403 inorganic & nuclear chemistry, Condensed Matter Physics, Ring (chemistry), Bioinformatics, Organic Papers, 01 natural sciences, Medicinal chemistry, 0104 chemical sciences, 3. Good health, chemistry.chemical_compound, QD901-999, General Materials Science, [CHIM.COOR]Chemical Sciences/Coordination chemistry, Flack parameter, Chirality (chemistry), Isopropyl
Abstract

The title compound, C27H34O2, was hemisynthesized through direct benzoylation of the naturally occurring meroterpene totarol. The central fused six-membered ring has a half-chair conformation, whereas the terminal six-membered ring displays a chair conformation. The dihedral angle between the fused benzene ring and the benzoyl benzene ring is 73.05 (14)°. TheS,Schirality of the molecule is consistent with the synthetic pathway, and confirmed by the refinement of the Flack parameter.

Published
2014
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25. Absolute configuration of (1S,3R,8R)-10-bromomethyl-2,2-dichloro-3,7,7-trimethyltricyclo[6.4.0.01,3]dodec-9-ene

Author

Abdelwahed Auhmani, My Youssef Ait Itto, Jean-Claude Daran, Abdoullah Bimoussa, and Aziz Auhmani

Subjects
Crystallography, Chemistry, Absolute configuration, General Chemistry, Condensed Matter Physics, computer.software_genre, Ring (chemistry), Organic Papers, Crystal, symbols.namesake, QD901-999, symbols, General Materials Science, Data mining, van der Waals force, computer, Ene reaction
Abstract

The absolute configuration of the title compound, C16H23BrCl2, has been deduced from the chemical pathway and fully confirmed by refinement of the Flack and Hooft parameters. The six-membered ring adopts a half-chair conformation, whereas the seven-membered ring is a twisted chair. The molecular packing within the crystal is stabilized only by van der Waals interactions.

Published
2013

26. 2-Isopropyl-4-methoxy-5-methylphenyl acetate

Author

E.H. Soumhi, Mohamed Driss, R. Oubabi, Abdelwahed Auhmani, and M.Y. Ait Itto

Subjects
Hydrogen bond, Phenyl acetate, General Chemistry, Dihedral angle, Condensed Matter Physics, Ring (chemistry), Bioinformatics, Medicinal chemistry, Organic Papers, Crystal, lcsh:Chemistry, chemistry.chemical_compound, Zigzag, chemistry, lcsh:QD1-999, General Materials Science, Benzene, Isopropyl
Abstract

In the title compound, C13H18O3, the benzene ring is almost perpendicular to the acetoxy plane, making a dihedral angle of 89.33 (11)°. In the crystal, molecules are linked by weak C—H...O hydrogen bonds, forming a zigzag chain along thec-axis direction.

Published
2013

30. Crystal structure of (1S,3R,8R,10S)-2,2-di-chloro-10-hy-droxy-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodecan-9-one.

Author

Benzalim A, Auhmani A, Ait Itto MY, Daran JC, and Abdelwahed A

Abstract

The asymmetric unit of the title compound, C16H24Cl2O2, contains two independent mol-ecules (A and B) which are built from three fused rings, viz. a seven-membered heptane ring, a six-membered cyclo-hexyl ring bearing a ketone and an alcohol group, and a cyclo-propane ring bearing two Cl atoms. In the crystal, the two mol-ecules are linked via two O-H⋯O hydrogen bonds, forming an A-B dimer with an R 2 (2)(10) ring motif. The A mol-ecules of these dimers are linked via a C-H⋯O hydrogen bond, forming chains propagating along the a-axis direction. Both mol-ecules have the same absolute configuration, i.e. 1S,3R,8R,10S, which is based on the synthetic pathway and further confirmed by resonant scattering [Flack parameter = 0.03 (5)].

Published
2016
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31. (1R,3S,8R)-3,7,7,10-Tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-en-11-one.

Author

Bimoussa A, Auhmani A, Ait Itto MY, Daran JC, and Abdelwahed A

Abstract

The absolute configuration of the title compound, C16H24O, has been deduced from the chemical pathway. The six-membered ring has a roughly half-chair conformation with the quaternary C atom as the flap. The seven-membered ring displays a chair conformation. In the crystal, there is a weak C-H⋯O hydrogen bond between the methyl-ene group of the cyclo-propane ring and the carbonyl group of a screw-axis-related mol-ecule, which builds up a zigzag-like chain along the b-axis direction.

Published
2013
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32. Absolute configuration of (1R,3S,8R,11R)-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-en-11-ol.

Author

Abdoullah B, Aziz A, Ait Itto MY, Daran JC, and Abdelwahed A

Abstract

The absolute configuration of the title compound, C16H26O, was determined as (1R,3S,8R,11R) based mainly on the synthetic pathway but is also implied by the X-ray analysis. The mol-ecule contains fused six- and seven-membered rings. Part of the seven-membered ring was refined as disordered over two sets of sites with the occupancy ratio fixed at 0.86:0.14. The disorder corresponds to a major chair conformation and a minor boat conforation. In the crysyal, O-H⋯O hydrogen bonds connect the mol-ecules into chains parallel to the a axis.

Published
2013
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