scholarly journals 1-{(E)-[4-(4-Hydroxyphenyl)butan-2-ylidene]amino}-3-phenylthiourea: crystal structure, Hirshfeld surface analysis and computational study

2021 ◽  
Vol 77 (8) ◽  
pp. 788-794
Author(s):  
Ming Yueh Tan ◽  
Huey Chong Kwong ◽  
Karen A. Crouse ◽  
Thahira B. S. A. Ravoof ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Computational Study ◽  
Molecular Packing ◽  
Hirshfeld Surface ◽  
Major Contributor ◽  
Aromatic Rings ◽  
Thiourea Derivative ◽  
Dispersion Energy ◽  
Layer Region ◽  
Imine Bond

The title thiourea derivative, C17H19N3OS, adopts a U-shaped conformation with the dihedral angle between the terminal aromatic rings being 73.64 (5)°. The major twist in the molecule occurs about the ethane bond with the Ci—Ce—Ce—Cb torsion angle being −78.12 (18)°; i = imine, e = ethane and b = benzene. The configuration about the imine bond is E, the N-bound H atoms lie on opposite sides of the molecule and an intramolecular amine-N—H...N(imine) hydrogen bond is evident. In the molecular packing, hydroxyl-O—H...S(thione) and amine-N—H...O hydrogen bonding feature within a linear, supramolecular chain. The chains are connected into a layer in the ab plane by a combination of methylene-C—H...S(thione), methylene-C—H...O(hydroxyl), methyl-C—H...π(phenyl) and phenyl-C—H...π(hydroxybenzene) interactions. The layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surface highlights the presence of weak methyl-C—H...O(hydroxyl) and H...H interactions in the inter-layer region. Computational chemistry indicates that dispersion energy is the major contributor to the overall stabilization of the molecular packing.

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.

scholarly journals Di-n-butyl[N′-(3-methoxy-2-oxidobenzylidene)-N-phenylcarbamohydrazonothioato]tin(IV): crystal structure, Hirshfeld surface analysis and computational study

2021 ◽  
Vol 77 (3) ◽  
pp. 286-293
Author(s):  
Enis Nadia Md Yusof ◽  
Huey Chong Kwong ◽  
Thiruventhan Karunakaran ◽  
Thahira B. S. A. Ravoof ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonding ◽  
Schiff Base ◽  
Computational Study ◽  
Hirshfeld Surface ◽  
Energy Term ◽  
Dispersion Energy ◽  
Trigonal Bipyramidal ◽  
Base Derivative ◽  
Layer Region

The title diorganotin Schiff base derivative, [Sn(C4H9)2(C15H13N3O2S)], features a penta-coordinated tin centre defined by the N,O,S-donor atoms of the di-anionic Schiff base ligand and two methylene-C atoms of the n-butyl substituents. The resultant C2NOS donor set defines a geometry intermediate between trigonal–bipyramidal and square-pyramidal. In the crystal, amine-N—H...O(methoxy) hydrogen bonding is found in a helical, supramolecular chain propagating along the b-axis direction. The chains are assembled into a layer parallel to (\overline{1}01) with methylene-C—H...π(phenyl) interactions prominent; layers stack without directional interactions between them. The analysis of the calculated Hirshfeld surface showed the presence of weak methylene-C—H...π(phenyl) interactions and short H...H contacts in the inter-layer region. Consistent with the nature of the identified contacts, the stabilization of the crystal is dominated by the dispersion energy term.

scholarly journals 1-Ethyl 2-methyl 3,4-bis(acetyloxy)pyrrolidine-1,2-dicarboxylate: crystal structure, Hirshfeld surface analysis and computational chemistry

2020 ◽  
Vol 76 (6) ◽  
pp. 967-972 ◽  
Author(s):  
Sofia Dallasta Pedroso ◽  
Ignez Caracelli ◽  
Julio Zukerman-Schpector ◽  
Monica Soto-Monsalve ◽  
Regina H. De Almeida Santos ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hirshfeld Surface ◽  
Double Layers ◽  
Equatorial Position ◽  
Two Dimensional ◽  
Energy Term ◽  
Pyrrolidine Ring ◽  
Dispersion Energy ◽  
Compound C ◽  
Layer Region

The title compound, C13H19NO8, is based on a tetra-substituted pyrrolidine ring, which has a twisted conformation about the central C—C bond; the Cm—Ca—Ca—Cme torsion angle is 38.26 (15)° [m = methylcarboxylate, a = acetyloxy and me = methylene]. While the N-bound ethylcarboxylate group occupies an equatorial position, the remaining substituents occupy axial positions. In the crystal, supramolecular double-layers are formed by weak methyl- and methylene-C—H...O(carbonyl) interactions involving all four carbonyl-O atoms. The two-dimensional arrays stack along the c axis without directional interactions between them. The Hirshfeld surface is dominated by H...H (55.7%) and H...C/C...H (37.0%) contacts; H...H contacts are noted in the inter-double-layer region. The interaction energy calculations point to the importance of the dispersion energy term in the stabilization of the crystal.

scholarly journals 4-Benzyl-1-(4-nitrophenyl)-1H-1,2,3-triazole: crystal structure and Hirshfeld analysis

2017 ◽  
Vol 73 (11) ◽  
pp. 1716-1720 ◽  
Author(s):  
Julio Zukerman-Schpector ◽  
Sofia Dallasta Pedroso ◽  
Lucas Sousa Madureira ◽  
Márcio Weber Paixão ◽  
Akbar Ali ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Torsion Angle ◽  
Title Compound ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Aromatic Rings ◽  
Compound C ◽  
Centroid Distance ◽  
Hirshfeld Analysis ◽  
Intermolecular Contacts

The molecule in the title compound, C15H12N4O2, has a twistedL-shape with the dihedral angle between the aromatic rings of the N-bound benzene and C-bound benzyl groups being 70.60 (9)°. The nitro group is co-planar with the benzene ring to which it is connected [C—C—N—O torsion angle = 0.4 (3)°]. The three-dimensional packing is stabilized by a combination of methylene-C—H...O(nitro), methylene-C—H...π(phenyl), phenyl-C—H...π(triazolyl) and nitro-O...π(nitrobenzene) interactions, along with weak π(triazolyl)–π(nitrobenzene) contacts [inter-centroid distance = 3.8386 (10) Å]. The importance of the specified intermolecular contacts has been verified by an analysis of the calculated Hirshfeld surface.

scholarly journals A cinnamaldehyde Schiff base ofS-(4-methylbenzyl) dithiocarbazate: crystal structure, Hirshfeld surface analysis and computational study

2017 ◽  
Vol 73 (4) ◽  
pp. 543-549 ◽  
Author(s):  
Enis Nadia Md Yusof ◽  
Mohamed I. M. Tahir ◽  
Thahira B. S. A. Ravoof ◽  
Sang Loon Tan ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Mirror Symmetry ◽  
Computational Study ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Hydrogen Atoms ◽  
Benzyl Substituent

The title dithiocarbazate ester (I), C18H18N2S2[systematic name: (E)-4-methylbenzyl 2-[(E)-3-phenylallylidene]hydrazinecarbodithioate, comprises an almost planar central CN2S2residue [r.m.s. deviation = 0.0131 Å]. The methylene(tolyl-4) group forms a dihedral angle of 72.25 (4)° with the best plane through the remaining non-hydrogen atoms [r.m.s. deviation = 0.0586 Å] so the molecule approximates mirror symmetry with the 4-tolyl group bisected by the plane. The configuration about both double bonds in the N—N=C—C=C chain isE; the chain has an alltransconformation. In the crystal, eight-membered centrosymmetric thioamide synthons, {...HNCS}2, are formedviaN—H...S(thione) hydrogen bonds. Connections between the dimersviaC—H...π interactions lead to a three-dimensional architecture. A Hirshfeld surface analysis shows that (I) possesses an interaction profile similar to that of a closely related analogue with anS-bound benzyl substituent, (II). Computational chemistry indicates the dimeric species of (II) connectedviaN—H...S hydrogen bonds is about 0.94 kcal mol−1more stable than that in (I).

scholarly journals 1-{(E)-[3-(1H-Imidazol-1-yl)-1-phenylpropylidene]amino}-3-(2-methylphenyl)urea

2012 ◽  
Vol 68 (6) ◽  
pp. o1848-o1849 ◽  
Author(s):  
Mohamed I. Attia ◽  
Mohamed N. Aboul-Enein ◽  
Nasser R. El-Brollosy ◽  
Seik Weng Ng ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Three Dimensional ◽  
Imidazole Ring ◽  
Dihedral Angles ◽  
Aromatic Rings ◽  
Compound C ◽  
Imine Bond ◽  
Supramolecular Chains

In the title compound, C20H21N5O, the conformation about the imine bond [1.289 (3) Å] is E. Overall, the molecule is disk-shaped with the imidazole ring located above the remainder of the molecule and with the dihedral angles of 10.97 (15) and 12.11 (15)°, respectively, between the imidazole ring and the phenyl and methylbenzene rings; the dihedral angle between the aromatic rings is 8.17 (14)°. Within the urea unit, the N—H atoms are anti to each other and one of the N—H atoms forms an intramolecular N—H...N hydrogen bond. Helical supramolecular chains along [001] are formed via N—H...N(imidazole) hydrogen bonds in the crystal structure. These are connected into a three-dimensional architecture by C—H...O(carbonyl) and C—H...π interactions.

scholarly journals Crystal structure and Hirshfeld surface analysis of (2E)-3-(3-bromo-4-fluorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one

2018 ◽  
Vol 74 (8) ◽  
pp. 1063-1066 ◽  
Author(s):  
S. N. Sheshadri ◽  
Zeliha Atioğlu ◽  
Mehmet Akkurt ◽  
M. K. Veeraiah ◽  
Ching Kheng Quah ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Aromatic Rings ◽  
Compound C ◽  
Graph Set

In the molecule of the title compound, C17H14BrFO3, the aromatic rings are tilted with respect to the enone bridge by 13.63 (14) and 4.27 (15)°, and form a dihedral angle 17.91 (17)°. In the crystal, centrosymmetrically related molecules are linked by pairs of C—H...O hydrogen bonds into dimeric units, forming rings of R 2 2(14) graph-set motif. The dimers are further connected by weak C—H...O hydrogen interactions, forming layers parallel to (10\overline{1}). Hirshfeld surface analysis shows that van der Waals interactions constitute the major contribution to the intermolecular interactions, with H...H contacts accounting for 29.7% of the surface.

scholarly journals Synthesis, crystal structure and Hirshfeld surface analysis of N-(4-chlorophenyl)-5-cyclopropyl-1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxamide

2020 ◽  
Vol 76 (5) ◽  
pp. 756-760
Author(s):  
Nazariy Pokhodylo ◽  
Yurii Slyvka ◽  
Volodymyr Pavlyuk
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Triazole Ring ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Frontier Molecular Orbitals ◽  
Asymmetric Unit ◽  
Aromatic Rings ◽  
Compound C ◽  
Subsequent Acid

The title compound, C19H17ClN4O2, was obtained via a two-step synthesis involving the enol-mediated click Dimroth reaction of 4-azidoanisole with methyl 3-cyclopropyl-3-oxopropanoate leading to the 5-cyclopropyl-1-(4-methoxyphenyl)-1H-1,2,3-triazole-4-carboxylic acid and subsequent acid amidation with 4-chloroaniline by 1,1′-carbonyldiimidazole (CDI). It crystallizes in space group P21/n, with one molecule in the asymmetric unit. In the extended structure, two molecules arranged in a near coplanar fashion relative to the triazole ring planes are interconnected by N—H...N and C—H...N hydrogen bonds into a homodimer. The formation of dimers is a consequence of the above interaction and the edge-to-face stacking of aromatic rings, which are turned by 58.0 (3)° relative to each other. The dimers are linked by C—H...O interactions into ribbons. DFT calculations demonstrate that the frontier molecular orbitals are well separated in energy and the HOMO is largely localized on the 4-chlorophenyl amide motif while the LUMO is associated with aryltriazole grouping. A Hirshfeld surface analysis was performed to further analyse the intermolecular interactions.

scholarly journals Synthesis and Crystal Structure of Bis(2-phenylpyridine-C,N’)-bis(acetonitrile)iridium(III)hexafluorophosphate Showing Three Anion/Cation Couples in the Asymmetric Unit

Crystals ◽  
2019 ◽  
Vol 9 (12) ◽  
pp. 617 ◽  
Author(s):  
Elisa Fresta ◽  
Marco Milanesio ◽  
Giorgio Volpi ◽  
Claudia Barolo ◽  
Eleonora Conterosito
Keyword(s):  
Crystal Structure ◽  
Title Compound ◽  
Driving Force ◽  
Hirshfeld Surface ◽  
Asymmetric Unit ◽  
Aromatic Rings ◽  
Synthesis And Crystal Structure ◽  
Space Group ◽  
Distorted Octahedral ◽  
Torsional Angles

The title compound bis(2-phenylpyridine-C,N’)-bis(acetonitrile)iridium(III)hexafluorophosphate, a six-coordinate iridium(III) complex, crystallizes in the P-1 space group. Iridium is in a distorted octahedral (n = 6) coordination with the N,C’ atoms of two phenylpyridine and the N atoms of two acetonitrile ligands. The peculiarity of this structure is that three independent moieties of the title compound and three PF6− anions, to counterbalance the charge, are observed in the asymmetric unit and this is a rather uncommon fact among the Cambridge Crystallographic Database (CSD) entries. The three couples are almost identical conformers with very similar torsional angles. The packing, symmetry, and space group were accurately analyzed and described also by means of Hirshfeld surface analysis, which is able to underline subtle differences among the three anion/cation couples in the asymmetric unit. The driving force of the packing is the clustering of the aromatic rings and the maximization of acetonitrile:PF6− interactions. The asymmetry of the cluster is the cause of the unusual number of moieties in the asymmetric unit.

scholarly journals Crystal structure and Hirshfeld surface analysis of 4-{2,2-dichloro-1-[(E)-(4-fluorophenyl)diazenyl]ethenyl}-N,N-dimethylaniline

2020 ◽  
Vol 76 (6) ◽  
pp. 811-815 ◽  
Author(s):  
Kadriye Özkaraca ◽  
Mehmet Akkurt ◽  
Namiq Q. Shikhaliyev ◽  
Ulviyya F. Askerova ◽  
Gulnar T. Suleymanova ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Two Dimensional ◽  
Aromatic Rings ◽  
Compound C

In the title compound, C16H14Cl2FN3, the dihedral angle between the two aromatic rings is 64.12 (14)°. The crystal structure is stabilized by a short Cl...H contact, C—Cl...π and van der Waals interactions. The Hirshfeld surface analysis and two-dimensional fingerprint plots show that H...H (33.3%), Cl...H/H...Cl (22.9%) and C...H/H...C (15.5%) interactions are the most important contributors towards the crystal packing.

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