scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of (S)-10-propargylpyrrolo[2,1-c][1,4]benzodiazepine-5,11-dione

2020 ◽  
Vol 76 (4) ◽  
pp. 467-472
Author(s):  
Dounia Jeroundi ◽  
Ahmed Mazzah ◽  
Tuncer Hökelek ◽  
El Mestafa El Hadrami ◽  
Catherine Renard ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C

The title compound, C15H14N2O2, consists of pyrrole and benzodiazepine units linked to a propargyl moiety, where the pyrrole and diazepine rings adopt half-chair and boat conformations, respectively. The absolute configuration was assigned on the the basis of L-proline, which was used in the synthesis of benzodiazepine. In the crystal, weak C—HBnz...ODiazp and C—HProprg...ODiazp (Bnz = benzene, Diazp = diazepine and Proprg = propargyl) hydrogen bonds link the molecules into two-dimensional networks parallel to the bc plane, enclosing R 4 4(28) ring motifs, with the networks forming oblique stacks along the a-axis direction. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (49.8%), H...C/C...H (25.7%) and H...O/O...H (20.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—H...O hydrogen-bond energies are 38.8 (for C—HBnz...ODiazp) and 27.1 (for C—HProprg...ODiazp) kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)-6-methoxyphenol

2020 ◽  
Vol 76 (5) ◽  
pp. 605-610
Author(s):  
Ballo Daouda ◽  
Nanou Tiéba Tuo ◽  
Tuncer Hökelek ◽  
Kangah Niameke Jean-Baptiste ◽  
Kodjo Charles Guillaume ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C

The title compound, C18H16N2O2, consists of perimidine and methoxyphenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar C4N2 ring adopting an envelope conformation with the NCN group hinged by 47.44 (7)° with respect to the best plane of the other five atoms. In the crystal, O—HPhnl...NPrmdn and N—HPrmdn...OPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Weak C—H...π interactions may further stabilize the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (49.0%), H...C/C...H (35.8%) and H...O/O...H (12.0%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the O—HPhnl...NPrmdn and N—HPrmdn...OPhnl hydrogen-bond energies are 58.4 and 38.0 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-chloroethyl 2-oxo-1-(prop-2-yn-1-yl)-1,2-dihydroquinoline-4-carboxylate

2019 ◽  
Vol 75 (10) ◽  
pp. 1411-1417
Author(s):  
Sonia Hayani ◽  
Yassir Filali Baba ◽  
Tuncer Hökelek ◽  
Fouad Ouazzani Chahdi ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C

The title compound, C15H12ClNO3, consists of a 1,2-dihydroquinoline-4-carboxylate unit with 2-chloroethyl and propynyl substituents, where the quinoline moiety is almost planar and the propynyl substituent is nearly perpendicular to its mean plane. In the crystal, the molecules form zigzag stacks along the a-axis direction through slightly offset π-stacking interactions between inversion-related quinoline moieties which are tied together by intermolecular C—HPrpnyl...OCarbx and C—HChlethy...OCarbx (Prpnyl = propynyl, Carbx = carboxylate and Chlethy = chloroethyl) hydrogen bonds. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (29.9%), H...O/O...H (21.4%), H...C/C... H (19.4%), H...Cl/Cl...H (16.3%) and C...C (8.6%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HPrpnyl...OCarbx and C—HChlethy...OCarbx hydrogen bond energies are 67.1 and 61.7 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of methyl 4-[3,6-bis(pyridin-2-yl)pyridazin-4-yl]benzoate

2019 ◽  
Vol 75 (11) ◽  
pp. 1672-1678
Author(s):  
Mouad Filali ◽  
Lhoussaine El Ghayati ◽  
Tuncer Hökelek ◽  
Joel T. Mague ◽  
Abdessalam Ben-Tama ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C

The title compound, C22H16N4O2, contains two pyridine rings and one methoxycarbonylphenyl group attached to a pyridazine ring which deviates very slightly from planarity. In the crystal, ribbons consisting of inversion-related chains of molecules extending along the a-axis direction are formed by C—HMthy...OCarbx (Mthy = methyl and Carbx = carboxylate) hydrogen bonds. The ribbons are connected into layers parallel to the bc plane by C—HBnz...π(ring) (Bnz = benzene) interactions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (39.7%), H...C/C...H (27.5%), H...N/N...H (15.5%) and O...H/H...O (11.1%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—HMthy...OCarbx hydrogen-bond energies are 62.0 and 34.3 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)phenol

2020 ◽  
Vol 76 (6) ◽  
pp. 798-802
Author(s):  
Ballo Daouda ◽  
Nanou Tiéba Tuo ◽  
Niameke Jean-Baptiste Kangah ◽  
Tuncer Hökelek ◽  
Charles Guillaume Kodjo ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Compound C ◽  
Independent Molecules

The asymmetric unit of the title compound, C17H14N2O, contains two independent molecules each consisting of perimidine and phenol units. The tricyclic perimidine units contain naphthalene ring systems and non-planar C4N2 rings adopting envelope conformations with the C atoms of the NCN groups hinged by 44.11 (7) and 48.50 (6)° with respect to the best planes of the other five atoms. Intramolecular O—H...N hydrogen bonds may help to consolidate the molecular conformations. The two independent molecules are linked through an N—H...O hydrogen bond. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (52.9%) and H...C/C...H (39.5%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 5-bromo-1-{2-[2-(2-chloroethoxy)ethoxy]ethyl}indoline-2,3-dione

2019 ◽  
Vol 75 (9) ◽  
pp. 1372-1378
Author(s):  
Omar Abdellaoui ◽  
Tuncer Hökelek ◽  
Frédéric Capet ◽  
Catherine Renard ◽  
Amal Haoudi ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Dimensional Structure ◽  
Compound C

The title compound, C14H15BrClNO4, consists of a 5-bromoindoline-2,3-dione unit linked to a 1-{2-[2-(2-chloroethoxy)ethoxy]ethyl} moiety. In the crystal, a series of C—H...O hydrogen bonds link the molecules to form a supramolecular three-dimensional structure, enclosing R 2 2(8), R 2 2(12), R 2 2(18) and R 2 2(22) ring motifs. π–π contacts between the five-membered dione rings may further stabilize the structure, with a centroid–centroid distance of 3.899 (2) Å. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (28.1%), H...O/O...H (23.5%), H...Br/Br...H (13.8%), H...Cl/Cl...H (13.0%) and H...C/C...H (10.2%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO—LUMO behaviour was elucidated to determine the energy gap. The chloroethoxyethoxyethyl side chain atoms are disordered over two sets of sites with an occupancy ratio of 0.665 (8):0.335 (6).

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 1,3-bis[2-methoxy-4-(prop-2-en-1-yl)phenoxy]propane

2020 ◽  
Vol 76 (3) ◽  
pp. 344-348 ◽  
Author(s):  
Abdelmaoujoud Taia ◽  
Mohamed Essaber ◽  
Tuncer Hökelek ◽  
Abdeljalil Aatif ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Molecular Structures ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C

The asymmetric unit of the title compound, C23H28O4, comprises two half-molecules, with the other half of each molecule being completed by the application of twofold rotation symmetry. The two completed molecules both have a V-shaped appearance but differ in their conformations. In the crystal, each independent molecule forms chains extending parallel to the b axis with its symmetry-related counterparts through C—H...π(ring) interactions. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (65.4%), H...C/C...H (21.8%) and H...O/O...H (12.3%) interactions. Optimized structures using density functional theory (DFT) at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structures in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 4-[(prop-2-en-1-yloxy)methyl]-3,6-bis(pyridin-2-yl)pyridazine

2019 ◽  
Vol 75 (9) ◽  
pp. 1321-1326 ◽  
Author(s):  
Mouad Filali ◽  
Nada Kheira Sebbar ◽  
Tuncer Hökelek ◽  
Joel T. Mague ◽  
Said Chakroune ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Hydrogen Bond Energy ◽  
Functional Theory ◽  
Compound C

The title compound, C18H16N4O, consists of a 3,6-bis(pyridin-2-yl)pyridazine moiety linked to a 4-[(prop-2-en-1-yloxy)methyl] group. The pyridine-2-yl rings are oriented at a dihedral angle of 17.34 (4)° and are rotated slightly out of the plane of the pyridazine ring. In the crystal, C—HPyrd...NPyrdz (Pyrd = pyridine and Pyrdz = pyridazine) hydrogen bonds and C—HPrpoxy...π (Prpoxy = prop-2-en-1-yloxy) interactions link the molecules, forming deeply corrugated layers approximately parallel to the bc plane and stacked along the a-axis direction. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (48.5%), H...C/C...H (26.0%) and H...N/N...H (17.1%) contacts, hydrogen bonding and van der Waals interactions being the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the C—HPyrd...NPyrdz hydrogen-bond energy is 64.3 kJ mol−1. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of ethyl 2-{4-[(2-ethoxy-2-oxoethyl)(phenyl)carbamoyl]-2-oxo-1,2-dihydroquinolin-1-yl}acetate

2019 ◽  
Vol 75 (11) ◽  
pp. 1753-1758
Author(s):  
Yassir Filali Baba ◽  
Sonia Hayani ◽  
Tuncer Hökelek ◽  
Manpreet Kaur ◽  
Jerry Jasinski ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Intermolecular Hydrogen Bond ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Compound C

The title compound, C24H24N2O6, consists of ethyl 2-(1,2,3,4-tetrahydro-2-oxoquinolin-1-yl)acetate and 4-[(2-ethoxy-2-oxoethyl)(phenyl)carbomoyl] units, where the oxoquinoline unit is almost planar and the acetate substituent is nearly perpendicular to its mean plane. In the crystal, C—HOxqn...OEthx and C—HPhyl...OCarbx (Oxqn = oxoquinolin, Ethx = ethoxy, Phyl = phenyl and Carbx = carboxylate) weak hydrogen bonds link the molecules into a three-dimensional network sturucture. A π–π interaction between the constituent rings of the oxoquinoline unit, with a centroid–centroid distance of 3.675 (1) Å may further stabilize the structure. Both terminal ethyl groups are disordered over two sets of sites. The ratios of the refined occupanies are 0.821 (8):0.179 (8) and 0.651 (18):0.349 (18). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (53.9%), H...O/O...H (28.5%) and H...C/C...H (11.8%) interactions. Weak intermolecular hydrogen-bond interactions and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) geometric optimized structures at the B3LYP/6-311G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO molecular orbital behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis, interaction energy, and DFT studies of cholesteryl heptanoate

2021 ◽  
Vol 77 (7) ◽  
pp. 686-691
Author(s):  
Nurcan Akduran ◽  
Tuncay Karakurt ◽  
Tuncer Hökelek
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Axis Direction ◽  
Compound C

The title compound, C34H58O2, consists of cholesteryl and heptanoate units, in which the six-membered rings adopt chair and twisted-boat conformations while the five-membered ring adopts an envelope conformation. In the crystal, the molecules are aligned along the a-axis direction and stacked along the b-axis direction. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (92.4%) and H...O/O...H (6.1%) interactions. van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/ 6–31 G(d) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap, and the molecular electrostatic potential (MEP) of the compound was investigated.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT study of (2Z)-2-(4-fluorobenzylidene)-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzothiazin-3-one

2019 ◽  
Vol 75 (3) ◽  
pp. 372-377 ◽  
Author(s):  
Brahim Hni ◽  
Nada Kheira Sebbar ◽  
Tuncer Hökelek ◽  
Younes Ouzidan ◽  
Ahmed Moussaif ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Boat Conformation ◽  
Compound C

The title compound, C18H12FNOS, is built up from a 4-fluorobenzylidene moiety and a dihydrobenzothiazine unit with a propynyl substituent, with the heterocyclic portion of the dihydrobenzothiazine unit adopting a shallow boat conformation with the propynyl substituent nearly perpendicular to it. The two benzene rings are oriented at a dihedral angle of 43.02 (6)°. In the crystal, C—HFlurphen...FFlurphen (Flurphen = fluorophenyl) hydrogen bonds link the molecules into inversion dimers, enclosing R 2 2(8) ring motifs, with the dimers forming oblique stacks along the a-axis direction. Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (33.9%), H...C/C...H (26.7%), H...F/F...H (10.9%) and C...C (10.6%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

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