scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 4-methyl-2-({[4-(trifluoromethyl)phenyl]imino}methyl)phenol

2020 ◽  
Vol 76 (8) ◽  
pp. 1325-1330
Author(s):  
Md. Serajul Haque Faizi ◽  
Emine Berrin Cinar ◽  
Onur Erman Dogan ◽  
Alev Sema Aydin ◽  
Erbil Agar ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C ◽  
The Density Functional Theory ◽  
Homo Lumo

The title compound, C15H12F3NO, crystallizes with one molecule in the asymmetric unit. The configuration of the C=N bond is E and there is an intramolecular O—H...N hydrogen bond present, forming an S(6) ring motif. The dihedral angle between the mean planes of the phenol and the 4-trifluoromethylphenyl rings is 44.77 (3)°. In the crystal, molecules are linked by C—H...O interactions, forming polymeric chains extending along the a-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from C...H/H...C (29.2%), H...H (28.6%), F...H/H...F (25.6%), O...H/H...O (5.7%) and F...F (4.6%) interactions. The density functional theory (DFT) optimized structure at the B3LYP/6-311 G(d,p) level is compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap. The crystal studied was refined as an inversion twin.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 6-bromo-3-(12-bromododecyl)-2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine

2020 ◽  
Vol 76 (5) ◽  
pp. 677-682 ◽  
Author(s):  
Zainab Jabri ◽  
Karim Jarmoni ◽  
Tuncer Hökelek ◽  
Joel T. Mague ◽  
Safia Sabir ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Side Chain ◽  
Functional Theory ◽  
Compound C ◽  
Homo Lumo

The title compound, C24H30Br2N4O2, consists of a 2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine entity with a 12-bromododecyl substituent attached to the pyridine N atom. The middle eight-carbon portion of the side chain is planar to within 0.09 (1) Å and makes a dihedral angle of 21.9 (8)° with the mean plane of the imidazolopyridine moiety, giving the molecule a V-shape. In the crystal, the imidazolopyridine units are associated through slipped π–π stacking interactions together with weak C—HPyr...ONtr and C—HBrmdcyl...ONtr (Pyr = pyridine, Ntr = nitro and Brmdcyl = bromododecyl) hydrogen bonds. The 12-bromododecyl chains overlap with each other between the stacks. The terminal –CH2Br group of the side chain shows disorder over two resolved sites in a 0.902 (3):0.098 (3) ratio. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (48.1%), H...Br/Br...H (15.0%) and H...O/O...H (12.8%) interactions. The optimized molecular structure, using density functional theory at the B3LYP/ 6–311 G(d,p) level, is compared with the experimentally determined 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 (E)-4-methyl-2-{[(4-methylphenyl)imino]methyl}phenol

2020 ◽  
Vol 76 (7) ◽  
pp. 1075-1079
Author(s):  
Nermin Kahveci Yagci ◽  
Md. Serajul Haque Faizi ◽  
Alev Sema Aydin ◽  
Necmi Dege ◽  
Onur Erman Dogan ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C ◽  
The Density Functional Theory ◽  
Homo Lumo

In the title compound, C15H15NO, the configuration of the C=N bond of the Schiff base is E, and an intramolecular O—H...N hydrogen bond is observed, forming an intramolecular S(6) ring motif. The phenol ring is inclined by 45.73 (2)° from the plane of the aniline ring. In the crystal, molecules are linked along the b axis by O—H...N and C—H...O hydrogen bonds, forming polymeric chains. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H...H (56.9%) and H...C/C...H (31.2%) interactions. The density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined molecular structure, and the HOMO–LUMO energy gap is provided. The crystal studied was refined as an inversion twin.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-4-methyl-2-{[(2-methyl-3-nitrophenyl)imino]methyl}phenol

2020 ◽  
Vol 76 (10) ◽  
pp. 1551-1556
Author(s):  
Emine Berrin Cinar ◽  
Md. Serajul Haque Faizi ◽  
Nermin Kahveci Yagci ◽  
Onur Erman Dogan ◽  
Alev Sema Aydin ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C ◽  
Homo Lumo ◽  
Phenol Ring

The title compound, C15H14N2O3, was prepared by condensation of 2-hydroxy-5-methyl-benzaldehyde and 2-methyl-3-nitro-phenylamine in ethanol. The configuration of the C=N bond is E. An intramolecular O—H...N hydrogen bond is present, forming an S(6) ring motif and inducing the phenol ring and the Schiff base to be nearly coplanar [C—C—N—C torsion angle of 178.53 (13)°]. In the crystal, molecules are linked by C—H...O interactions, forming chains along the b-axis direction. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (37.2%), C...H (30.7%) and O...H (24.9%) interactions. The gas phase density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level is compared to 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 DFT study of N-(2-amino-5-methylphenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide

2021 ◽  
Vol 77 (6) ◽  
pp. 638-642
Author(s):  
Gamal Al Ati ◽  
Karim Chkirate ◽  
Joel T. Mague ◽  
Nadeem Abad ◽  
Redouane Achour ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Layer Structure ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Lumo Energy ◽  
Functional Theory ◽  
Homo Lumo

The title molecule, C13H16N4O, adopts an angular conformation. In the crystal a layer structure is generated by N—H...O and N—H...N hydrogen bonds together with C—H...π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (53.8%), H...C/C...H (21.7%), H...N/N...H (13.6%), and H...O/O...H (10.8%) interactions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 5.0452 eV.

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 (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one

2019 ◽  
Vol 75 (1) ◽  
pp. 58-63 ◽  
Author(s):  
Muhamad Fikri Zaini ◽  
Ibrahim Abdul Razak ◽  
Mohamad Zahid Anis ◽  
Suhana Arshad
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Significant Contribution ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Basis Set ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Homo Lumo

The asymmetric unit of the title halogenated chalcone derivative, C15H10BrFO, contains two independent molecules, both adopting an s-cis configuration with respect to the C=O and C=C bonds. In the crystal, centrosymmetrically related molecules are linked into dimers via intermolecular hydrogen bonds, forming rings with R 1 2(6), R 2 2(10) and R 2 2(14) graph-set motifs. The dimers are further connected by C—H...O interactions into chains parallel to [001]. A Hirshfeld surface analysis suggests that the most significant contribution to the crystal packing is by H...H contacts (26.3%). Calculations performed on the optimized structure obtained using density functional theory (DFT) at B3LYP with the 6–311 G++(d,p) basis set reveal that the HOMO–LUMO energy gap is 4.12 eV, indicating the suitability of this crystal for optoelectronic and biological applications. The nucleophilic and electrophilic binding site regions are elucidated using the molecular electrostatic potential (MEP).

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.

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