2,4-Diamino-6-phenyl-1,3,5-triazin-1-ium nitrate: intriguing crystal structure with high Z′/Z′′ and hydrogen bond numbers and Hirshfeld surface analysis of intermolecular interactions

CrystEngComm ◽  
2021 ◽  
Author(s):  
Nicoleta Caimac ◽  
Elena Melnic ◽  
Diana Chisca ◽  
Marina S. Fonari
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Surface Analysis ◽  
Intermolecular Interactions ◽  
Title Compound ◽  
Ionic Species ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Asymmetric Unit ◽  
Space Group

The title compound crystallises in the triclinic centrosymmetric space group P1̄ with an intriguing high number of crystallographically unique binary salt-like adducts (Z′ = 8) and a total number of ionic species (Z′′ = 16) in the asymmetric unit.

scholarly journals (3aS,4R,5R,6S,7aR)-4,5-Dibromo-2-[4-(trifluoromethyl)phenyl]-2,3,3a,4,5,6,7,7a-octahydro-3a,6-epoxy-1H-isoindol-1-one: crystal structure and Hirshfeld surface analysis

2021 ◽  
Vol 77 (5) ◽  
pp. 466-472
Author(s):  
Dmitriy F. Mertsalov ◽  
Kseniia A. Alekseeva ◽  
Magrycheva S. Daria ◽  
Maxim E. Cheshigin ◽  
Sevim Türktekin Çelikesir ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Asymmetric Unit ◽  
Compound C ◽  
Independent Molecules ◽  
Molecular Layers

The asymmetric unit of the title compound, C15H12Br2F3NO2, consists of two crystallographically independent molecules. In both molecules, the pyrrolidine and tetrahydrofuran rings adopt an envelope conformation. In the crystal, molecule pairs generate centrosymmetric rings with R 2 2(8) motifs linked by C—H...O hydrogen bonds. These pairs of molecules form a tetrameric supramolecular motif, leading to molecular layers parallel to the (100) plane by C—H...π and C—Br...π interactions. Interlayer van der Waals and interhalogen interactions stabilize molecular packing. The F atoms of the CF3 groups of both molecules are disordered over two sets of sites with refined site occupancies of 0.60 (3)/0.40 (3) and 0.640 (15)/0.360 (15). The most important contributions to the surface contacts of both molecules are from H...H (23.8 and 22.4%), Br...H/H...Br (18.3 and 12.3%), O...H/H...O (14.3 and 9.7%) and F...H/H...F (10.4 and 19.1%) interactions, as concluded from a Hirshfeld surface analysis.

scholarly journals Crystal structure and Hirshfeld surface analysis of methyl 1-(2,4-dichlorobenzyl)-5-methyl-1H-pyrazole-3-carboxylate

2018 ◽  
Vol 9 (4) ◽  
pp. 347-352
Author(s):  
Abdullah Aydin ◽  
Mehmet Akkurt ◽  
Zehra Tugce Gur ◽  
Erden Banoglu
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Crystal Data ◽  
Asymmetric Unit ◽  
Triclinic Space Group ◽  
Intermolecular Contacts

The title compound, C13H12Cl2N2O2, crystallizes with six molecules in the asymmetric unit, such that, the 1H-pyrazole rings are essentially planar. The six molecules are stabilized by intramolecular C-H···N and C-H···Cl interactions and the crystal structure is stabilized by intermolecular C-H···O hydrogen bonds, forming molecular sheets into paralel to the (-1 1 0) plane. These sheets are connected to each other by C-H···O hydrogen bonds and C-H···π interactions. In the Hirshfeld surface analysis, the H···H, Cl···H/H···Cl, C···H/H···C, O···H/H···O, N···H/H···N, Cl···Cl, Cl···O/O···Cl interactions add to 95.8% of the intermolecular contacts of the Hirshfeld surface area. The remaining contributions (2.9%) correspond to Cl···C/C···Cl, C···O/O···C, O···O and N···N interactions. Crystal Data for C13H12Cl2N2O2 (M = 299.15 g/mol): Triclinic, space group P-1 (no. 2), a = 12.0505(10) Å, b = 12.3189(11) Å, c = 29.184(3) Å, α = 88.565(4)°, β = 89.296(4)°, γ = 76.833(4)°, V = 4217.0(7) Å3, Z = 12, T = 296(2) K, μ(MoKα) = 0.460 mm-1, Dcalc = 1.414 g/cm3, 83073 reflections measured (2.8° ≤ 2Θ ≤ 47°), 12426 unique (Rint = 0.0411, Rsigma = 0.0235) which were used in all calculations. The final R1 was 0.0662 (I > 2σ(I)) and wR2 was 0.2481 (all data).

scholarly journals Crystal structure of N,N,N′,N′-tetramethylethanediamine

2022 ◽  
Vol 78 (1) ◽  
Author(s):  
Tobias Schrimpf ◽  
Felix Otte ◽  
Carsten Strohmann
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Intermolecular Interactions ◽  
Title Compound ◽  
Van Der Waals ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Organolithium Chemistry ◽  
Amine Ligand

The title compound N,N,N′,N′-tetramethylethanediamine, C6H16N2, is a bidentate amine ligand commonly used in organolithium chemistry for deaggregation. Crystals were grown at 243 K from n-pentane solution. The complete molecule is generated by a crystallographic center of symmetry and the conformation of the diamine is antiperiplanar. To investigate the intermolecular interactions, a Hirshfeld surface analysis was performed. It showed that H...H (van der Waals) interactions dominate with a contact percentage of 92.3%.

scholarly journals Crystal structure, DFT calculations and Hirshfeld surface analysis of 3-(4-methylphenyl)-6-nitro-1H-indazole

2018 ◽  
Vol 74 (12) ◽  
pp. 1857-1861 ◽  
Author(s):  
Ali Ben-Yahia ◽  
Youness El Bakri ◽  
Chin-Hung Lai ◽  
El Mokhtar Essassi ◽  
Joel T. Mague
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Dft Calculations ◽  
Surface Analysis ◽  
Title Compound ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Asymmetric Unit ◽  
Compound C ◽  
Independent Molecules

The asymmetric unit of the title compound, C14H11N3O3, consists of two independent molecules having very similar conformations in which the indazole moieties are planar. The independent molecules are distinguished by small differences in the rotational orientations of the nitro groups. In the crystal, N—H...O and C—H...O hydrogen bonds form zigzag chains along the b-axis direction. Additional C—H...O hydrogen bonds link the chains into layers parallel to (10\overline{1}). These are connected by slipped π-stacking and C—H...π(ring) interactions.

scholarly journals 2-[(1E)-({[(Benzylsulfanyl)methanethioyl]amino}imino)methyl]-6-methoxyphenol: crystal structure and Hirshfeld surface analysis

2016 ◽  
Vol 72 (4) ◽  
pp. 516-521 ◽  
Author(s):  
Enis Nadia Md Yusof ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink ◽  
Thahira B. S. A. Ravoof
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Surface Analysis ◽  
Intermolecular Interactions ◽  
Phenyl Ring ◽  
Hirshfeld Surface ◽  
Geometric Parameters ◽  
Hirshfeld Surface Analysis

The title dithiocarbazate ester, C16H16N2O2S2, comprises two almost planar residues,i.e. the phenyl ring and the remaining 14 non-H atoms (r.m.s. deviation = 0.0410 Å). These are orientated perpendicularly, forming a dihedral angle of 82.72 (5)°. An intramolecular hydroxy-O—H...N(imine) hydrogen bond, leading to anS(6) loop, is noted. An analysis of the geometric parameters is consistent with the molecule existing as the thione tautomer, and the conformation about the C=N bond isE. The thione S and imine H atoms lie to the same side of the molecule, facilitating the formation of intermolecular N—H...S hydrogen bonds leading to eight-membered {...HNCS}2synthons in the crystal. These aggregates are connected by phenyl-C—H...O(hydroxy) interactions into a supramolecular layer in thebcplane; these stack with no directional interactions between them. An analysis of the Hirshfeld surface confirms the nature of the intermolecular interactions.

scholarly journals (E)-1-(Anthracen-9-yl)-3-(2-chloro-6-fluorophenyl)prop-2-en-1-one: crystal structure and Hirshfeld surface analysis

2016 ◽  
Vol 72 (5) ◽  
pp. 648-651 ◽  
Author(s):  
Amzar Ahlami Abdullah ◽  
Nur Hafiq Hanif Hassan ◽  
Suhana Arshad ◽  
Nuridayanti Che Khalib ◽  
Ibrahim Abdul Razak
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Compound C ◽  
Centrosymmetric Dimers ◽  
Ring Motif

In the title compound, C23H14ClFO, the enone moiety adopts anEconformation. The dihedral angle between the benzene and anthracene ring is 63.42 (8)° and an intramolecular C—H...F hydrogen bond generates anS(6) ring motif. In the crystal, molecules are arranged into centrosymmetric dimersviapairs of C—H...F hydrogen bonds. The crystal structure also features C—H...π and π–π interactions. Hirshfeld surface analysis was used to confirm the existence of intermolecular interactions.

scholarly journals Crystal structure and Hirshfeld surface analysis of N-[(Z)-(2-hydroxyphenyl)methylidene]aniline N-oxide

2021 ◽  
Vol 77 (6) ◽  
pp. 596-599
Author(s):  
Shaaban K. Mohamed ◽  
Awad I. Said ◽  
Joel T. Mague ◽  
Moustafa F. Aly ◽  
Mehmet Akkurt ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Compound C

The conformation of the title compound, C13H11NO2, is partially determined by a strong, intramolecular O—H...O hydrogen bond. The crystal packing consists of strongly corrugated layers parallel to the ac plane and associated through C—H...π(ring) interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most significant contributions to the crystal packing are from H...H (44.1%), C...H/H...C (29.4%) and O...H/H...O (17.3%) contacts.

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 Conformational dimorphism of 2,2′-methylenebis(isoindoline-1,3-dione)

2019 ◽  
Vol 75 (1) ◽  
pp. 49-52
Author(s):  
Tze Shyang Chia ◽  
Huey Chong Kwong ◽  
Ai Jia Sim ◽  
Weng Zhun Ng ◽  
Qin Ai Wong ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Intermolecular Interactions ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Asymmetric Unit ◽  
Molecular Conformations ◽  
Space Group ◽  
Lattice Energies

In this study, a new monoclinic polymorph (space group C2/c) of 2,2′-methylenebis(isoindoline-1,3-dione), C17H10N2O4, is reported and compared to the previously reported triclinic polymorph (space group P\overline{1}). Similarly, both polymorphs consist of a unique molecule in the asymmetric unit (Z′ = 1). The molecular conformations of the two polymorphs are very similar, as shown by the r.m.s. deviation of 0.368 Å (excluding all H atoms). The intermolecular interactions of both polymorphs are described along with the Hirshfeld surface analysis, and the lattice energies are calculated.

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.

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