scholarly journals 2-[(2,4,6-Trimethylbenzene)sulfonyl]phthalazin-1(2H)-one: crystal structure, Hirshfeld surface analysis and computational study

2020 ◽  
Vol 76 (5) ◽  
pp. 697-702
Author(s):  
David Chukwuma Izuogu ◽  
Jonnie Niyi Asegbeloyin ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Computational Study ◽  
Hirshfeld Surface ◽  
Stacking Interactions ◽  
Interaction Energies ◽  
X Ray ◽  
Hirshfeld Surfaces ◽  
Π Stacking ◽  
Centroid Distance ◽  
Dispersion Terms

The X-ray crystal structure of the title phthalazin-1-one derivative, C17H16N2O3S {systematic name: 2-[(2,4,6-trimethylbenzene)sulfonyl]-1,2-dihydrophthalazin-1-one}, features a tetrahedral sulfoxide-S atom, connected to phthalazin-1-one and mesityl residues. The dihedral angle [83.26 (4)°] between the organic substituents is consistent with the molecule having the shape of the letter V. In the crystal, phthalazinone-C6-C—H...O(sulfoxide) and π(phthalazinone-N2C4)–π(phthalazinone-C6) stacking [inter-centroid distance = 3.5474 (9) Å] contacts lead to a linear supramolecular tape along the a-axis direction; tapes assemble without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of the C—H...O and π-stacking interactions but, also H...H and C—H...C contacts. The calculation of the interaction energies indicate the importance of dispersion terms with the greatest energies calculated for the C—H...O and π-stacking interactions.

scholarly journals 2-{(1E)-[(E)-2-(2,6-Dichlorobenzylidene)hydrazin-1-ylidene]methyl}phenol: crystal structure, Hirshfeld surface analysis and computational study

2019 ◽  
Vol 75 (10) ◽  
pp. 1423-1428 ◽  
Author(s):  
Rohit B. Manawar ◽  
Mitesh B. Gondaliya ◽  
Manish K. Shah ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Computational Study ◽  
Hirshfeld Surface ◽  
Stacking Interactions ◽  
Interaction Energies ◽  
Compound C ◽  
Hirshfeld Surfaces ◽  
Π Stacking ◽  
Schiff Base Compound ◽  
Van Der Waals Radii ◽  
Base Compound

The title Schiff base compound, C14H10Cl2N2O, features an E configuration about each of the C=N imine bonds. Overall, the molecule is approximately planar with the dihedral angle between the central C2N2 residue (r.m.s. deviation = 0.0371 Å) and the peripheral hydroxybenzene and chlorobenzene rings being 4.9 (3) and 7.5 (3)°, respectively. Nevertheless, a small twist is evident about the central N—N bond [the C—N—N—C torsion angle = −172.7 (2)°]. An intramolecular hydroxy-O—H...N(imine) hydrogen bond closes an S(6) loop. In the crystal, π–π stacking interactions between hydroxy- and chlorobenzene rings [inter-centroid separation = 3.6939 (13) Å] lead to a helical supramolecular chain propagating along the b-axis direction; the chains pack without directional interactions between them. The calculated Hirshfeld surfaces point to the importance of H...H and Cl...H/H...Cl contacts to the overall surface, each contributing approximately 29% of all contacts. However, of these only Cl...H contacts occur at separations less than the sum of the van der Waals radii. The aforementioned π–π stacking interactions contribute 12.0% to the overall surface contacts. The calculation of the interaction energies in the crystal indicates significant contributions from the dispersion term.

scholarly journals 2-[(1E)-[(Z)-2-({[(1Z)-[(E)-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study

2020 ◽  
Vol 76 (8) ◽  
pp. 1245-1250
Author(s):  
Georgiana Paulus ◽  
Huey Chong Kwong ◽  
Karen A. Crouse ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Torsion Angle ◽  
Computational Study ◽  
Hirshfeld Surface ◽  
Interaction Energies ◽  
Orthogonal Relationship ◽  
Hirshfeld Surfaces ◽  
Layer Region ◽  
Imine Bond ◽  
Dispersion Term

The complete molecule of the title hydrazine carbodithioate derivative, C32H30N4O2S4, is generated by a crystallographic twofold axis that bisects the disulfide bond. The molecule is twisted about this bond with the C—S—S—C torsion angle of 90.70 (8)° indicating an orthogonal relationship between the symmetry-related halves of the molecule. The conformation about the imine bond [1.282 (2) Å] is E and there is limited delocalization of π-electron density over the CN2C residue as there is a twist about the N—N bond [C—N—N—C torsion angle = −166.57 (15)°]. An intramolecular hydroxyl-O—H...N(imine) hydrogen bond closes an S(6) loop. In the crystal, methylene-C—H...π(tolyl) contacts assemble molecules into a supramolecular layer propagating in the ab plane: the layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of H...H contacts, which contribute 46.7% of all contacts followed by H...C/C...H contacts [25.5%] reflecting, in part, the C—H...π(tolyl) contacts. The calculation of the interaction energies confirm the importance of the dispersion term and the influence of the stabilizing H...H contacts in the inter-layer region.

X-ray Crystal Structure of Gallium Tris- (8-hydroxyquinoline):  Intermolecular π−π Stacking Interactions in the Solid State

1999 ◽  
Vol 11 (3) ◽  
pp. 530-532 ◽  
Author(s):  
Yue Wang ◽  
Weixing Zhang ◽  
Yanqin Li ◽  
Ling Ye ◽  
Guangdi Yang
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Stacking Interactions ◽  
X Ray ◽  
Π Stacking

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 4-(furan-2-yl)-2-(6-methyl-2,4-dioxopyran-3-ylidene)-2,3,4,5-tetrahydro-1H-1,5-benzodiazepine

2021 ◽  
Vol 77 (8) ◽  
pp. 834-838
Author(s):  
Mohamed El Hafi ◽  
Sanae Lahmidi ◽  
Lhoussaine El Ghayati ◽  
Tuncer Hökelek ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Energy Calculation ◽  
Boat Conformation ◽  
Stacking Interactions ◽  
Π Stacking

The title compound {systematic name: (S,E)-3-[4-(furan-2-yl)-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-2-ylidene]-6-methyl-2H-pyran-2,4(3H)-dione}, C19H16N2O4, is constructed from a benzodiazepine ring system linked to furan and pendant dihydropyran rings, where the benzene and furan rings are oriented at a dihedral angle of 48.7 (2)°. The pyran ring is modestly non-planar [largest deviation of 0.029 (4) Å from the least-squares plane] while the tetrahydrodiazepine ring adopts a boat conformation. The rotational orientation of the pendant dihydropyran ring is partially determined by an intramolecular N—HDiazp...ODhydp (Diazp = diazepine and Dhydp = dihydropyran) hydrogen bond. In the crystal, layers of molecules parallel to the bc plane are formed by N—HDiazp...ODhydp hydrogen bonds and slipped π–π stacking interactions. The layers are connected by additional slipped π–π stacking interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (46.8%), H...O/O...H (23.5%) and H...C/C...H (15.8%) interactions, indicating that van der Waals interactions are the dominant forces in the crystal packing. Computational chemistry indicates that in the crystal the N—H...O hydrogen-bond energy is 57.5 kJ mol−1.

Synthesis and crystal structure of a novel prochiral ketoimine: (E)-acetophenoneO-diphenylphosphoryl oxime

2015 ◽  
Vol 71 (3) ◽  
pp. 181-184
Author(s):  
Sean H. Majer ◽  
Joseph M. Tanski
Keyword(s):  
Crystal Structure ◽  
Solid State ◽  
Stacking Interactions ◽  
Synthesis And Crystal Structure ◽  
X Ray ◽  
Face To Face ◽  
Π Stacking

A novel activated prochiral ketoimine, (E)-acetophenoneO-diphenylphosphoryl oxime, C20H18NO2P, with an electron-withdrawing substituent on the imine N atom similar to other prochiral ketoimines, has been synthesized and the X-ray crystal stucture determined. The molecules pack together in the solid stateviaweak intermolecular C—H...O interactions and both face-to-face and edge-to-face π-stacking interactions.

scholarly journals N-Methyl-N-nitroso-p-toluenesulfonamide

2014 ◽  
Vol 70 (7) ◽  
pp. o782-o782
Author(s):  
Kartik Rai ◽  
Vincent Wu ◽  
Priya Gupta ◽  
David A. Laviska ◽  
Benny C. Chan
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Title Compound ◽  
Methyl Groups ◽  
Stacking Interactions ◽  
Aromatic Rings ◽  
Compound C ◽  
Π Stacking ◽  
Centroid Distance

The crystal structure of the title compound, C8H10N2O3S, displays predominant C—H...O hydrogen-bonding and π–π stacking interactions. The hydrogen bonds are between the O atoms of the sulfonyl group and H atoms on methyl groups. The π–π stacking interactions occur between adjacent aromatic rings, with a centroid–centroid distance of 3.868 (11) Å. These interactions lead to the formation of chains parallel to (101).

scholarly journals Crystal structure of diethyl {2,2,2-trichloro-1-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)-4-methylpentanamido]ethyl}phosphonate

2018 ◽  
Vol 74 (7) ◽  
pp. 915-917
Author(s):  
V. S. Brovarets ◽  
O. V. Golovchenko ◽  
E. B. Rusanov ◽  
J. A. Rusanova
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Stacking Interactions ◽  
Compound C ◽  
Π Stacking ◽  
Centroid Distance ◽  
Acceptor Atom ◽  
The Mean

In the title phosphorylated compound, C20H26Cl3N2O6P, the phthalimide unit is essentially planar (r.m.s. deviation = 0.0129 Å) and the O atoms of this unit deviate from the mean plane by 0.080 (3) and 0.041 (3) Å. In the crystal, pairs of molecules are linked by N—H...O and weak C—H...O hydrogen bonds involving the same acceptor atom, forming inversion dimers. In addition, π–π stacking interactions between the phthalimide groups, with a centroid–centroid distance of 3.7736 (13) Å, and further weak C—H...O hydrogen bonds connect the inversion dimers into columns along [0-11].

scholarly journals 3-(2-Pyridyl)-5-(4-pyridyl)-4-(p-tolyl)-1H-1,2,4-triazole

2009 ◽  
Vol 65 (6) ◽  
pp. o1225-o1225
Author(s):  
Lu-Tong Yuan ◽  
Hai Zhang ◽  
Zuo-Xiang Wang ◽  
Zhi-Rong Qu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Title Compound ◽  
Triazole Ring ◽  
Dihedral Angles ◽  
Stacking Interactions ◽  
Compound C ◽  
Hydrogen Bonding Interactions ◽  
Π Stacking ◽  
Centroid Distance

In the molecule of the title compound, C19H15N5, the dihedral angles formed by the plane of the triazole ring with those of the 2-pyridyl, 4-pyridyl andp-tolyl rings are 28.12 (10), 34.62 (10) and 71.43 (9)°, respectively. The crystal structure is consolidated by C—H...π hydrogen-bonding interactions and by π–π stacking interactions, with a centroid–centroid distance of 3.794 (4) Å.

scholarly journals A 2:1 co-crystal ofp-nitrobenzoic acid andN,N′-bis(pyridin-3-ylmethyl)ethanediamide: crystal structure and Hirshfeld surface analysis

2016 ◽  
Vol 72 (1) ◽  
pp. 76-82 ◽  
Author(s):  
Sabrina Syed ◽  
Siti Nadiah Abdul Halim ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Dihedral Angles ◽  
Inversion Symmetry ◽  
Stacking Interactions ◽  
Nitrobenzoic Acid ◽  
Hirshfeld Surfaces ◽  
Centroid Distance ◽  
Benzene Rings

The title 2:1 co-crystal, 2C7H5NO4·C14H14N4O2, in which the complete diamide molecule is generated by crystallographic inversion symmetry, features a three-molecule aggregate sustained by hydroxyl-O—H...N(pyridyl) hydrogen bonds. Thep-nitrobenzoic acid molecule is non-planar, exhibiting twists of both the carboxylic acid and nitro groups, which form dihedral angles of 10.16 (9) and 4.24 (4)°, respectively, with the benzene ring. The diamide molecule has a conformation approximating to a Z shape, with the pyridyl rings lying to either side of the central, almost planar diamide residue (r.m.s. deviation of the eight atoms being 0.025 Å), and forming dihedral angles of 77.22 (6)° with it. In the crystal, three-molecule aggregates are linked into a linear supramolecular ladder sustained by amide-N—H...O(nitro) hydrogen bonds and orientated along [10-4]. The ladders are connected into a double layerviapyridyl- and benzene-C—H...O(amide) interactions, which, in turn, are connected into a three-dimensional architectureviaπ–π stacking interactions between pyridyl and benzene rings [inter-centroid distance = 3.6947 (8) Å]. An evaluation of the Hirshfeld surfaces confirm the importance of intermolecular interactions involving oxygen atoms as well as the π–π interactions.

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