scholarly journals Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 9-(3-bromo-4-hydroxy-5-methoxyphenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

2021 ◽  
Vol 77 (11) ◽  
pp. 1170-1174
Author(s):  
N. Suresh Babu ◽  
V. Sughanya ◽  
D. Praveenkumar ◽  
M. L. Sundararajan
Keyword(s):  
Title Compound ◽  
Crystal Packing ◽  
Chemical Reactivity ◽  
Hirshfeld Surface ◽  
Frontier Molecular Orbital ◽  
Boat Conformation ◽  
Pyran Ring ◽  
Compound C ◽  
Molecular Orbital Analysis ◽  
Fused Ring System

In the fused ring system of the title compound, C24H27BrO5, the mean plane and maximum deviations of the central pyran ring are 0.0384 (2) and 0.0733 (2) Å, respectively. The cyclohexenone rings both adopt envelope conformations with the tetra-substituted C atoms as flap atoms, whereas the central pyran ring adopts a flattened boat conformation. The central pyran and phenyl substituent rings are almost perpendicular to each other, making a dihedral angle of 89.71 (2)°. In the crystal, pairs of molecules are linked via O—H...O hydrogen bonds, forming inversion dimers with an R 2 2(20) ring motif. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (50.6%), O...H/H...O (22.9%) and C...H/H...C (11.1%) contacts. Quantum chemical calculations for the frontier molecular orbitals were undertaken to determine the chemical reactivity of the title compound.

scholarly journals Crystal structure, Hirshfeld surface and frontier molecular orbital analysis of 10-benzyl-9-(3-ethoxy-4-hydroxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

2020 ◽  
Vol 76 (4) ◽  
pp. 585-588
Author(s):  
N. Suresh Babu ◽  
V. Sughanya ◽  
A. Dhandapani ◽  
R. Kalaivanan
Keyword(s):  
Title Compound ◽  
Crystal Packing ◽  
Chemical Reactivity ◽  
Hirshfeld Surface ◽  
Frontier Molecular Orbital ◽  
Helical Chain ◽  
Boat Conformation ◽  
Compound C ◽  
The Mean ◽  
Dihydropyridine Ring

In the fused ring system of the title compound, C32H37NO4, the central dihydropyridine ring adopts a flattened boat conformation, the mean and maximum deviations of the dihydropyridine ring being 0.1429 (2) and 0.2621 (2) Å, respectively. The two cyclohexenone rings adopt envelope conformations with the tetrasubstituted C atoms as flap atoms. The benzene and phenyl rings form dihedral angles of 85.81 (2) and 88.90 (2)°, respectively, with the mean plane of the dihydropyridine ring. In the crystal, molecules are linked via an O—H...O hydrogen bond, forming a helical chain along the b-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (65.2%), O...H/H...O (18.8%) and C...H/H...C (13.9%) contacts. Quantum chemical calculations for the frontier molecular orbitals were undertake to determine the chemical reactivity of the title compound.

scholarly journals 12-(3,4,5-Trimethoxyphenyl)-2,3,4,12-tetrahydro-1H-5-oxatetraphen-1-one: crystal structure and Hirshfeld surface analysis

2016 ◽  
Vol 72 (6) ◽  
pp. 809-814
Author(s):  
Mukesh M. Jotani ◽  
P. Iniyavan ◽  
V. Vijayakumar ◽  
S. Sarveswari ◽  
Yee Seng Tan ◽  
...  
Keyword(s):  
Least Squares ◽  
Dihedral Angle ◽  
Title Compound ◽  
Molecular Conformation ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Boat Conformation ◽  
Pyran Ring ◽  
Π Interactions ◽  
Compound C

In the title compound, C26H24O5, the pyran ring has a flattened-boat conformation, with the 1,4-related ether O and methine C atoms lying 0.1205 (18) and 0.271 (2) Å, respectively, above the least-squares plane involving the doubly bonded C atoms (r.m.s deviation = 0.0208 Å). An envelope conformation is found for the cyclohexene ring, with the flap atom being the middle methylene C atom, lying 0.616 (2) Å out of the plane defined by the remaining atoms (r.m.s. deviation = 0.0173 Å). The fused four-ring system is approximately planar, with the dihedral angle between the least-squares planes through the cyclohexene and naphthyl rings being 10.78 (7)°. The trisubstituted benzene ring occupies a position almost perpendicular to the pyran ring [dihedral angle = 83.97 (4)°]. The most prominent feature of the packing is the formation of zigzag supramolecular chains mediated by aryl-C—H...O(methoxy) interactions; chains are connected into a three-dimensional architecture by methylene- and methyl-C—H...π interactions. The prevalence of C—H...O and C—H...π interactions is confirmed by an analysis of the Hirshfeld surface. A comparison with related structures suggests that the molecular conformation of the title compound is relatively robust with respect to varying substitution patterns at the methine C atom of the pyran ring.

scholarly journals Crystal structure of 3-amino-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile

2015 ◽  
Vol 71 (7) ◽  
pp. o481-o482 ◽  
Author(s):  
Mehmet Akkurt ◽  
Peter N. Horton ◽  
Shaaban K. Mohamed ◽  
Sabry H. H. Younes ◽  
Mustafa R. Albayati
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Crystal Packing ◽  
Ring System ◽  
Boat Conformation ◽  
Naphthalene Ring ◽  
Pyran Ring ◽  
Compound C ◽  
The Mean

In the title compound, C20H13ClN2O, the chlorobenzene ring is almost perpendicular to the mean plane of the naphthalene ring system, making a dihedral angle of 81.26 (8)°. The 4H-pyran ring fused with the naphthalene ring system has a flattened boat conformation. In the crystal, N—H...N hydrogen bonds generate chains along theb-axis direction. Further N—H...N hydrogen bonds link these chains into sheets parallel to (010). The crystal packing also features C—H...π interactions. The crystal studied was an inversion twin with a 0.557 (16):0.443 (16) domain ratio.

scholarly journals Crystal structure, Hirshfeld surface analysis and HOMO–LUMO analysis of (E)-N′-(3-hydroxy-4-methoxybenzylidene)nicotinohydrazide monohydrate

2019 ◽  
Vol 75 (6) ◽  
pp. 804-807
Author(s):  
Palaniyappan Sivajeyanthi ◽  
Bellarmin Edison ◽  
Kasthuri Balasubramani ◽  
Ganesan Premkumar ◽  
Toka Swu
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Frontier Molecular Orbital ◽  
Compound C ◽  
Molecular Orbital Analysis ◽  
Homo Lumo ◽  
Orbital Analysis

The molecule of the title Schiff base compound, C14H13N3O3·H2O, displays a trans configuration with respect to the C=N bond. The dihedral angle between the benzene and pyridine rings is 29.63 (7)°. The crystal structure features intermolecular N—H...O, C—H...O, O—H...O and O—H...N hydrogen-bonding interactions, leading to the formation of a supramolecular framework. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (37.0%), O...H/H...O (23.7%)), C...H/H...C (17.6%) and N...H/H...N (11.9%) interactions. The title compound has also been characterized by frontier molecular orbital analysis.

scholarly journals Crystal structure, Hirshfeld surface analysis and HOMO–LUMO analysis of (E)-4-bromo-N′-(4-methoxybenzylidene)benzohydrazide

2018 ◽  
Vol 74 (10) ◽  
pp. 1500-1503 ◽  
Author(s):  
Kasthuri Balasubramani ◽  
Ganesan Premkumar ◽  
Palaniyappan Sivajeyanthi ◽  
Muthaiah Jeevaraj ◽  
Bellarmin Edison ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Frontier Molecular Orbital ◽  
Compound C ◽  
Dimensional Network ◽  
Molecular Orbital Analysis ◽  
Homo Lumo

The title Schiff base compound, C15H13BrN2O2, displays an E configuration with respect to the C=N double bond, which forms a dihedral angle of 58.06 (9)° with the benzene ring. In the crystal, the molecules are linked into chains parallel to the b axis by N—H...O and C—H...O hydrogen bonds, giving rise to rings with an R 2 1(6) graph-set motif. The chains are further linked into a three-dimensional network by C—H...π interactions. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from C...H (33.2%), H...H (27.7%), Br...H/H...Br (14.2%) and O...H/H...O (13.6%) interactions. The title compound has also been characterized by frontier molecular orbital analysis.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy, DFT and antibacterial activity studies of (Z)-4-hexyl-2-(4-methylbenzylidene)-2H-benzo[b][1,4]thiazin-3(4H)-one

2020 ◽  
Vol 76 (6) ◽  
pp. 889-895
Author(s):  
Ghizlane Sebbar ◽  
Brahim Hni ◽  
Tuncer Hökelek ◽  
Joel T. Mague ◽  
Nada Kheira Sebbar ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Antibacterial Activity ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Boat Conformation ◽  
Compound C

The title compound, C22H25NOS, consists of methylbenzylidene and benzothiazine units linked to a hexyl moiety, where the thiazine ring adopts a screw-boat conformation. In the crystal, inversion dimers are formed by weak C—HMthn...OBnzthz hydrogen bonds and are linked into chains extending along the a-axis direction by weak C—HBnz...OBnzthz (Bnz = benzene, Bnzthz = benzothiazine and Mthn = methine) hydrogen bonds. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (59.2%) and H...C/C...H (27.9%) 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—HBnz...OBnzthz and C—HMthn...OBnzthz hydrogen-bond energies are 75.3 and 56.5 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. Moreover, the antibacterial activity of the title compound was evaluated against gram-positive and gram-negative bacteria.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy, DFT and antibacterial activity studies of ethyl 2-[(2Z)-2-(2-chlorobenzylidene)-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl]acetate

2020 ◽  
Vol 76 (5) ◽  
pp. 629-636
Author(s):  
Ghizlane Sebbar ◽  
Ellouz Mohamed ◽  
Tuncer Hökelek ◽  
Joel T. Mague ◽  
Nada Kheira Sebbar ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Antibacterial Activity ◽  
Surface Analysis ◽  
Title Compound ◽  
Density Functional ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Boat Conformation ◽  
Compound C

The title compound, C19H16ClNO3S, consists of chlorophenyl methylidene and dihydrobenzothiazine units linked to an acetate moiety, where the thiazine ring adopts a screw-boat conformation. In the crystal, two sets of weak C—HPh...ODbt (Ph = phenyl and Dbt = dihydrobenzothiazine) hydrogen bonds form layers of molecules parallel to the bc plane. The layers stack along the a-axis direction with intercalation of the ester chains. The crystal studied was a two component twin with a refined BASF of 0.34961 (5). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (37.5%), H...C/C...H (24.6%) and H...O/O...H (16.7%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—HPh...ODbt hydrogen bond energies are 38.3 and 30.3 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. Moreover, the antibacterial activity of the title compound has been evaluated against gram-positive and gram-negative bacteria.

scholarly journals 4-(4-Methoxyphenyl)-5,7-dimethylchroman-2-one

IUCrData ◽  
2016 ◽  
Vol 1 (3) ◽  
Author(s):  
Jaqueline Evangelista Queiroz ◽  
Giuliana Muniz Vila Verde ◽  
Mariette Miguens Pereira ◽  
Manuela Ramos Silva ◽  
Gilberto L. B. Aquino
Keyword(s):  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Title Compound ◽  
Boat Conformation ◽  
Pyran Ring ◽  
Axis Direction ◽  
Π Interactions ◽  
Microwave Assisted ◽  
Compound C ◽  
The Mean

In the title compound, C18H18O3, a dihydrocoumarin synthesizedviaa microwave-assisted hydroarylation reaction, the 4-methoxyphenyl ring is inclined to the mean plane of the coumarin moiety by 78.21 (9)°. The pyran ring has a screw-boat conformation and its mean plane is inclined to the fused benzene ring by 13.88 (11)°. In the crystal, molecules are linkedviaC—H...O hydrogen bonds, forming ribbons along theb-axis direction. The ribbons are linkedviaC—H...π interactions, forming slabs parallel to theabplane.

scholarly journals (Z)-4-n-Butyl-2-(4-chlorobenzylidene)-2H-1,4-benzothiazin-3(4H)-one

IUCrData ◽  
2017 ◽  
Vol 2 (6) ◽  
Author(s):  
Mohamed Ellouz ◽  
Nada Kheira Sebbar ◽  
Younes Ouzidan ◽  
Manpreet Kaur ◽  
El Mokhtar Essassi ◽  
...  
Keyword(s):  
Hydrogen Bond ◽  
Dihedral Angle ◽  
Intermolecular Interactions ◽  
Title Compound ◽  
Crystal Packing ◽  
Boat Conformation ◽  
Compound C ◽  
Phenyl Rings

In the title compound, C19H18ClNOS, the thiazin-3-one ring adopts a slightly distorted screw-boat conformation. An intramolecular C—H...S hydrogen bond encloses anS(6) ring and affects the overall conformation of the molecule. The dihedral angle between the two phenyl rings is 52.3 (2)°. In the crystal, weak C—H...O intermolecular interactions stabilize the crystal packing.

scholarly journals 9-(2,4-Dinitrophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione

2013 ◽  
Vol 69 (2) ◽  
pp. o281-o281 ◽  
Author(s):  
N. Sureshbabu ◽  
V. Sughanya
Keyword(s):  
Dihedral Angle ◽  
Title Compound ◽  
Maximum Deviation ◽  
Boat Conformation ◽  
Pyran Ring ◽  
Compound C ◽  
The Mean

In the title compound, C23H24N2O7, the central 4H-pyran ring adopts a flattened boat conformation, whereas both cyclohexenone rings adopt envelope conformations, the C atom bearing the dimethyl substituent being the flap atom in each case. The mean and maximum deviation of the pyran ring are 0.0379 (4) and 0.0605 (3) Å. The mean plane of the pyran ring and the dinitrobenzene ring make a dihedral angle of 85.88 (2)°.

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