Crystal structure, Hirshfeld surface analysis and Pixel calculations of the monohydrate of (E)-3-(2-hydroxy-5-methoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one: occurrence of π interactions

2021 ◽  
Vol 76 (1) ◽  
pp. 27-38
Author(s):  
Ligia R. Gomes ◽  
John N. Low ◽  
Alan B. Turner ◽  
James L. Wardell
Keyword(s):  
Crystal Structure ◽  
Water Molecule ◽  
Surface Analysis ◽  
Small Deviation ◽  
Lattice Energy ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Face To Face ◽  
Π Interactions ◽  
Detailed Structural Analysis

Abstract A detailed structural analysis has been carried out on the monohydrate of (E)-3-(2-hydroxy-5-methoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one, 1·H 2 O. The molecule, 1, shows a small deviation from planarity with an interplanar angle between the phenyl groups of 13.32(6)°. Classical O–H⋯O hydrogen bonds involving the water molecule play significant roles in determining the overall structure. The chalcone molecules in the structure are linked directly by C–H⋯O and off-set face-to-face π⋯π intermolecular interactions, as well as indirectly via interactions involving the water molecule in an elaborate spiralling hydrogen bonding scheme. The relative contributions of various intermolecular contacts were investigated using Hirshfeld surface analysis and the associated two dimensional fingerprint plots. Pairs of molecules were identified in the crystal structure using the Pixel method. The Pixel lattice energy calculations revealed that the dispersion and the Coulombic components were the major contributors to the packing stabilization. Comparisons were made between the structures of 1·H 2 O and hydroxylated (E)-3-(2-hydroxyphenyl)-1-phenyl-prop-2-en-1-one derivatives, in particular in regards to the participation of π interactions.

scholarly journals 6-Methyl-2-oxo-N-(quinolin-6-yl)-2H-chromene-3-carboxamide: crystal structure and Hirshfeld surface analysis

2016 ◽  
Vol 72 (8) ◽  
pp. 1121-1125
Author(s):  
Lígia R. Gomes ◽  
John Nicolson Low ◽  
André Fonseca ◽  
Maria João Matos ◽  
Fernanda Borges
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Surface Analysis ◽  
Coumarin Derivative ◽  
Hirshfeld Surface ◽  
Supramolecular Structures ◽  
Hirshfeld Surface Analysis ◽  
Quinoline Ring ◽  
Π Interactions

The title coumarin derivative, C20H14N2O3, displays intramolecular N—H...O and weak C—H...O hydrogen bonds, which probably contribute to the approximate planarity of the molecule [dihedral angle between the coumarin and quinoline ring systems = 6.08 (6)°]. The supramolecular structures feature C—H...O hydrogen bonds and π–π interactions, as confirmed by Hirshfeld surface analyses.

scholarly journals Bis{4-methylbenzyl 2-[4-(propan-2-yl)benzylidene]hydrazinecarbodithioato-κ2N2,S}nickel(II): crystal structure and Hirshfeld surface analysis

2017 ◽  
Vol 73 (3) ◽  
pp. 397-402 ◽  
Author(s):  
Enis Nadia Md Yusof ◽  
Thahira B. S. A. Ravoof ◽  
Mohamed I. M. Tahir ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Chelate Ring ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Planar Geometry ◽  
Π Interactions ◽  
Centroid Distance ◽  
Square Planar

The complete molecule of the title hydrazine carbodithioate complex, [Ni(C19H21N2S2)2], is generated by the application of a centre of inversion. The NiIIatom isN,S-chelated by two hydrazinecarbodithioate ligands, which provide atrans-N2S2donor set that defines a distorted square-planar geometry. The conformation of the five-membered chelate ring is an envelope with the NiIIatom being the flap atom. In the crystal,p-tolyl-C—H...π(benzene-iPr),iPr-C—H...π(p-tolyl) and π–π interactions [betweenp-tolyl rings with inter-centroid distance = 3.8051 (12) Å] help to consolidate the three-dimensional architecture. The analysis of the Hirshfeld surface confirms the importance of H-atom contacts in establishing the packing.

A structural framework of biologically active coumarin derivatives: crystal structure and Hirshfeld surface analysis

CrystEngComm ◽  
2014 ◽  
Vol 16 (29) ◽  
pp. 6654-6663 ◽  
Author(s):  
Magdalena Małecka ◽  
Elzbieta Budzisz
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Hirshfeld Surface ◽  
Biologically Active ◽  
Hirshfeld Surface Analysis ◽  
Coumarin Derivatives ◽  
Π Interactions ◽  
Structural Framework ◽  
Lipophilicity Parameter

The relation between the lipophilicity parameter (log P) and the contribution of C–H⋯π interactions to the Hirshfeld surface has been investigated.

scholarly journals Crystal structure and Hirshfeld surface analysis of the naturally occurring cassane-type diterpenoid, 6β-cinnamoyl-7β-hydroxyvouacapen-5α-ol

2018 ◽  
Vol 74 (3) ◽  
pp. 385-389 ◽  
Author(s):  
K. Osahon Ogbeide ◽  
Rajesh Kumar ◽  
Mujeeb-Ur-Rehman ◽  
Bodunde Owolabi ◽  
Abiodun Falodun ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Π Interactions ◽  
Compound C ◽  
Naturally Occurring

The title compound, C29H36O5, a cassane-type diterpenoid {systematic name: (4aR,5R,6R,6aS,7R,11aS,11bR)-4a,6-dihydroxy-4,4,7,11b-tetramethyl-1,2,3,4,4a,5,6,6a,7,11,11a,11b-dodecahydrophenanthro[3,2-b]furan-5-yl 3-phenylprop-2-enoate}, was isolated from a medicinally important plant,Caesalpinia pulcherrima(Fabaceae). In the molecule, three cyclohexane rings aretrans-fused and adopt chair, chair and half-chair conformations. In the crystal, molecules are linkedviaO—H...O hydrogen bonds, forming a tape structure along theb-axis direction. The tapes are further linked into a double-tape structure through C—H...π interactions. The Hirshfeld surface analysis indicates that the contributions to the crystal packing are H...H (65.5%), C...H (18.7%), O...H (14.5%) and C...O (0.3%).

scholarly journals Crystal structure and Hirshfeld surface analysis of (E)-1-(2,6-dichlorophenyl)-2-(2-nitrobenzylidene)hydrazine

2020 ◽  
Vol 76 (8) ◽  
pp. 1173-1178 ◽  
Author(s):  
Sevim Türktekin Çelikesir ◽  
Mehmet Akkurt ◽  
Namiq Q. Shikhaliyev ◽  
Gulnar T. Suleymanova ◽  
Gulnare V. Babayeva ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Benzene Ring ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Face To Face ◽  
Ring Form ◽  
Compound C ◽  
Molecular Layers

In the title compound, C13H9Cl2N3O2, the 2,6-dichlorophenyl ring and the nitro-substituted benzene ring form a dihedral angle of 21.16 (14)°. In the crystal, face-to-face π–π stacking interactions occur along the a-axis direction between the centroids of the 2,6-dichlorophenyl ring and the nitro-substituted benzene ring. Furthermore, these molecules show intramolecular N—H...Cl and C—H...O contacts and are linked by intermolecular N—H...O and C—H...Cl hydrogen bonds, forming pairs of hydrogen-bonded molecular layers parallel to (20\overline{2}). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (23.0%), O...H/H...O (20.1%), Cl...H/H...Cl (19.0%), C...C (11.2%) and H...C/C...H (8.0%) interactions.

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

2019 ◽  
Vol 75 (8) ◽  
pp. 1190-1194
Author(s):  
Mehmet Akkurt ◽  
Namiq Q. Shikhaliyev ◽  
Ulviyya F. Askerova ◽  
Sevinc H. Mukhtarova ◽  
Gunay Z. Mammadova ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Benzene Ring ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Stacking Interactions ◽  
Aromatic Rings ◽  
Face To Face ◽  
Compound C

In the title compound, C16H11Cl2N3O, the 4-methoxy-substituted benzene ring makes a dihedral angle of 41.86 (9)° with the benzene ring of the benzonitrile group. In the crystal, molecules are linked into layers parallel to (020) by C—H...O contacts and face-to-face π–π stacking interactions [centroid–centroid distances = 3.9116 (14) and 3.9118 (14) Å] between symmetry-related aromatic rings along the a-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from Cl...H/H...Cl (22.8%), H...H (21.4%), N...H/H...N (16.1%), C...H/H...C (14.7%) and C...C (9.1%) interactions.

scholarly journals Crystal structure, Hirshfeld surface analysis and computational study of a rhodamine B–salicylaldehyde Schiff base derivative

2020 ◽  
Vol 76 (7) ◽  
pp. 1027-1032
Author(s):  
Songwut Suramitr ◽  
Jitpinan Teanwarawat ◽  
Nuttapong Ithiapa ◽  
Worawat Wattanathana ◽  
Anwaraporn Suramitr
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Hydroxyl Group ◽  
Quaternary Carbon Atom ◽  
Π Interactions

The molecular structure of the title compound {systematic name: 3′,6′-bis(diethylamino)-2-[(2-hydroxybenzylidene)amino]spiro[isoindoline-1,9′-xanthen]-3-one}, C35H36N4O3 or RbSa, can be seen as being composed of two parts sharing a central quaternary carbon atom. Both the xanthene and isoindole moieties are nearly planar: 14 atoms in the former moiety show an r.m.s. deviation of 0.0411 Å and eleven atoms in the latter moiety show an r.m.s. deviation of 0.0545 Å. These two planes are almost perpendicular to each other, the angle between the mean planes being 87.71 (2)°. The title compound appears to be in its enol form. The corresponding H atom was located and freely refined at a distance of 1.02 (3) Å from the O atom and 1.72 (2) Å from the N atom. The strong intramolecular hydrogen bond O—H...N bridging the hydroxyl group and its neighboring nitrogen atom forms an S(6) graph-set motif. Apart from the intramolecular O—H...N hydrogen bond, C—H...O interactions are observed between two neighbouring RbSa molecules related by an inversion center. The C—O donor–acceptor distance is 3.474 (2) Å. Moreover, C—H...π interactions are observed between the C—H bond of one of the ethyl groups and the centroid of the benzene ring of the isoindole moiety. The C...centroid distance is 3.8191 (15) Å. No π–π interactions are observed in the crystal structure as the shortest distance between ring centroids is more than 4 Å. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H, C...H/H...C, O...H/H...O and N...H/H...N interactions. DFT calculations at the CAM-B3LYP/6–31 G(d) level were carried out to gain a better understanding of the relative energies and the tautomerization process between two possible conformers (keto and enol), as well as the transition state of the title compound.

scholarly journals Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-fluorophenyl)ethenyl]diazene

2019 ◽  
Vol 75 (4) ◽  
pp. 465-469 ◽  
Author(s):  
Namiq Q. Shikhaliyev ◽  
Sevim Türktekin Çelikesir ◽  
Mehmet Akkurt ◽  
Khanim N. Bagirova ◽  
Gulnar T. Suleymanova ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Stacking Interactions ◽  
Face To Face ◽  
Compound C

In the title compound, C14H8Cl3FN2, the planes of the 4-fluorophenyl ring and the 4-chlorophenyl ring make a dihedral angle of 56.13 (13)°. In the crystal, molecules are stacked in a column along the a axis via a weak C—H...Cl hydrogen bond and face-to-face π–π stacking interactions [centroid–centroid distances = 3.8615 (18) and 3.8619 (18) Å]. The crystal packing is further stabilized by short Cl...Cl contacts. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from Cl...H/H...Cl (31.2%), H...H (14.8%), C...H/H...C (14.0%), F...H/H...F (12.8%), C...C (9.0%) and Cl...Cl (6.7%) interactions.

scholarly journals trans-Dichloridobis(dimethyl sulfoxide-κO)bis(4-fluorobenzyl-κC1)tin(IV): crystal structure and Hirshfeld surface analysis

2017 ◽  
Vol 73 (5) ◽  
pp. 667-672 ◽  
Author(s):  
Nur Adibah Binti Mohd Amin ◽  
Rusnah Syahila Duali Hussen ◽  
See Mun Lee ◽  
Nathan R. Halcovitch ◽  
Mukesh M. Jotani ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Dimethyl Sulfoxide ◽  
Surface Analysis ◽  
Three Dimensional ◽  
Molecular Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Coordination Geometry ◽  
Π Interactions ◽  
Dimensional Network

The SnIVatom in the title diorganotin compound, [Sn(C7H6F)2Cl2(C2H6OS)2], is located on a centre of inversion, resulting in the C2Cl2O2donor set having an all-transdisposition of like atoms. The coordination geometry approximates an octahedron. The crystal features C—H...F, C—H...Cl and C—H...π interactions, giving rise to a three-dimensional network. The respective influences of the Cl...H/H...Cl and F...H/H...F contacts to the molecular packing are clearly evident from the analysis of the Hirshfeld surface.

scholarly journals Crystal structure and Hirshfeld surface analysis of (aqua-κO)(methanol-κO)[N-(2-oxidobenzylidene)threoninato-κ3 O,N,O′]copper(II)

2020 ◽  
Vol 76 (9) ◽  
pp. 1539-1542
Author(s):  
Natsuki Katsuumi ◽  
Yuika Onami ◽  
Sayantan Pradhan ◽  
Tomoyuki Haraguchi ◽  
Takashiro Akitsu
Keyword(s):  
Crystal Structure ◽  
Water Molecule ◽  
Surface Analysis ◽  
Complex Molecule ◽  
Hirshfeld Surface ◽  
Title Complex ◽  
Hirshfeld Surface Analysis ◽  
Tridentate Ligand ◽  
Pyramidal Geometry ◽  
Square Pyramidal Geometry

In the title complex molecule, [Cu(C11H11NO4)(CH4O)(H2O)], the Cu atom is coordinated in a distorted square-pyramidal geometry by a tridentate ligand synthesized from L-threonine and salicylaldehyde, one methanol molecule and one water molecule. In the crystal, the molecules show intra- and intermolecular O—H...O hydrogen bonds. The Hirshfeld surface analysis indicates that the most important contributions to the packing are H...H (49.4%) and H...O/O...H (31.3%) contacts.

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