scholarly journals Crystal structure and Hirshfeld surface analysis of two 5,11-methanobenzo[g][1,2,4]triazolo[1,5-c][1,3,5]oxadiazocine derivatives

2019 ◽  
Vol 75 (4) ◽  
pp. 492-498
Author(s):  
Mustafa Kemal Gumus ◽  
Sevgi Kansiz ◽  
Cigdem Yuksektepe Ataol ◽  
Necmi Dege ◽  
Igor O. Fritsky
Keyword(s):  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Pyridine Ring ◽  
Molecular Electrostatic Potential ◽  
Potential Surface ◽  
Crystal Packing ◽  
Triazole Ring ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Molecular Electrostatic Potential Surface

In the title compounds, 9-bromo-2,5-dimethyl-11,12-dihydro-5H-5,11-methanobenzo[g][1,2,4]triazolo[1,5-c][1,3,5]oxadiazocine, C13H13BrN4O (I), and 7-methoxy-5-methyl-2-(pyridin-4-yl)-11,12-dihydro-5H-5,11-methanobenzo[g][1,2,4]triazolo[1,5-c][1,3,5]oxadiazocine, C18H17N5O2 (II), the triazole ring is inclined to the benzene ring by 85.15 (9) and 76.98 (5)° in compounds I and II, respectively. In II, the pyridine ring is almost coplanar with the triazole ring, having a dihedral angle of 4.19 (8)°. In the crystal of I, pairs of N—H...N hydrogen bonds link the molecules to form inversion dimers with an R 2 2(8) ring motif. The dimers are linked by C—H...π and C—Br...π interactions forming layers parallel to the bc plane. In the crystal of II, molecules are linked by N—H...N and C—H...O hydrogen bonds forming chains propagating along the b-axis direction. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, and the molecular electrostatic potential surface was also analysed. The Hirshfeld surface analysis of I suggests that the most significant contributions to the crystal packing are H...H (42.4%) and O...H/H...O (17.9%) contacts. For compound II, the H...H (48.5%), C...H/H...C (19.6%) and N...H/H...N (16.9%) interactions are the most important contributions.

scholarly journals Crystal structure and Hirshfeld surface analysis of 4-(2,6-dichlorobenzyl)-6-phenylpyridazin-3(2H)-one

2019 ◽  
Vol 75 (5) ◽  
pp. 650-654 ◽  
Author(s):  
Fouad El Kali ◽  
Sevgi Kansiz ◽  
Said Daoui ◽  
Rafik Saddik ◽  
Necmi Dege ◽  
...  
Keyword(s):  
Dihedral Angle ◽  
Surface Analysis ◽  
Title Compound ◽  
Molecular Electrostatic Potential ◽  
Potential Surface ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Compound C ◽  
Molecular Electrostatic Potential Surface

The asymmetric unit of the title compound, C17H12Cl2N2O, contains one independent molecule. The molecule is not planar, the phenyl and pyridazine rings are twisted with respect to each other, making a dihedral angle of 29.96 (2)° and the dichlorophenyl ring is nearly perpendicular to the pyridazine ring, with a dihedral angle of 82.38 (11)°. In the crystal, pairs of N—H...O hydrogen bonds link the molecules to form inversion dimers with an R 2 2(8) ring motif. The dimers are linked by C—H...O interactions, forming layers parallel to the bc plane. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, and the molecular electrostatic potential surface was also analysed. The Hirshfeld surface analysis of the title compound suggests that the most significant contributions to the crystal packing are by H...H (31.4%), Cl...H/H...Cl (19.9%) and C...H/H...C (19%) contacts.

scholarly journals Crystal structure and Hirshfeld surface analysis of (2E,2′E)-1,1′-[selenobis(4,1-phenylene)]bis[3-(4-chlorophenyl)prop-2-en-1-one]

2019 ◽  
Vol 75 (11) ◽  
pp. 1724-1728
Author(s):  
Hazem Bouraoui ◽  
Youcef Mechehoud ◽  
Souheyla Chetioui ◽  
Rachid Touzani ◽  
Meriem Medjani ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Molecular Electrostatic Potential ◽  
Potential Surface ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Two Dimensional ◽  
Compound C ◽  
Benzene Rings ◽  
Molecular Electrostatic Potential Surface

In the title compound, C30H20Cl2O2Se, the C—Se—C angle is 99.0 (2)°, with the dihedral angle between the planes of the attached benzene rings being 79.1 (3)°. The average endocyclic angles (Se—C—C) facing the Se atom are 122.1 (5) and 122.2 (5)°. The Se atom is essentially coplanar with the attached benzene rings, deviating by 0.075 (1) and 0.091 (1) Å. In the two phenylene(4-chlorophenyl)prop-2-en-1-one units, the benzene rings are inclined to each other by 44.6 (3) and 7.8 (3)°. In the crystal, the molecules stack up the a axis, forming layers parallel to the ac plane. There are no significant classical intermolecular interactions present. Hirshfeld surface analysis, two-dimensional fingerprint plots and the molecular electrostatic potential surface were used to analyse the crystal packing. The Hirshfeld surface analysis suggests that the most significant contributions to the crystal packing are by C...H/H...C contacts (17.7%).

scholarly journals Hirshfeld surface analysis and crystal structure of 7-methoxy-5-methyl-2-phenyl-11,12-dihydro-5,11-methano-1,2,4-triazolo[1,5-c][1,3,5]benzoxadiazocine

2018 ◽  
Vol 74 (9) ◽  
pp. 1211-1214 ◽  
Author(s):  
Mustafa Kemal Gumus ◽  
Sevgi Kansiz ◽  
Necmi Dege ◽  
Valentina A. Kalibabchuk
Keyword(s):  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Triazole Ring ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Supramolecular Network ◽  
Compound C ◽  
Benzene Rings

The title compound, C19H18N4O2, crystallizes with two independent molecules in the asymmetric unit. The triazole ring is inclined to the benzene rings by 9.63 (13) and 87.37 (12)° in one molecule, and by 4.46 (13) and 86.15 (11)° in the other. In the crystal, classical N—H...N hydrogen bonds, weak C—H...O hydrogen bonds and weak C—H...π interactions link the molecules into a three-dimensional supramolecular network. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to investigate the intermolecular interactions present in the crystal, indicating that the most important contributions for the crystal packing are from H...H (51.4%), H...C/C...H (26.7%), H...O/O...H (8.9%) and H...N/N...H (8%) interactions.

scholarly journals Crystal structure and Hirshfeld surface analysis of ethyl 2-{4-[(3-methyl-2-oxo-1,2-dihydroquinoxalin-1-yl)methyl]-1H-1,2,3-triazol-1-yl}acetate

2018 ◽  
Vol 74 (11) ◽  
pp. 1648-1652 ◽  
Author(s):  
Nadeem Abad ◽  
Youssef Ramli ◽  
Tuncer Hökelek ◽  
Nada Kheira Sebbar ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Triazole Ring ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Compound C ◽  
Π Stacking ◽  
Centroid Distance

The molecule of the title compound, C16H17N5O3, is build up from two fused six-membered rings linked to a 1,2,3-triazole ring, which is attached to an ethyl azido-acetate group. The dihydroqinoxalinone portion is planar to within 0.0512 (12) Å and is oriented at a dihedral angle of 87.83 (5)° with respect to the pendant triazole ring. In the crystal, a combination of intermolecular C—H...O and C—H...N hydrogen bonds together with slipped π-stacking [centroid–centroid distance = 3.7772 (12) Å] and C—H...π (ring) interactions lead to the formation of chains extending along the c-axis direction. Additional C—H...O hydrogen bonds link these chains into layers parallel to the bc plane and the layers are tied together by complementary π-stacking [centroid–centroid distance = 3.5444 (12) Å] interactions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (44.5%), H...O/O...H (18.8%), H...N/N...H (17.0%) and H...C/C...H (10.4%) interactions.

scholarly journals Crystal structure and Hirshfeld surface analysis of ethyl 2-({5-acetyl-3-cyano-6-methyl-4-[(E)-2-phenylethenyl]pyridin-2-yl}sulfanyl)acetate

2021 ◽  
Vol 77 (7) ◽  
pp. 730-733
Author(s):  
Safiyyah A. H. Al-Waleedy ◽  
Shaaban K. Mohamed ◽  
Joel T. Mague ◽  
Mehmet Akkurt ◽  
Mohamed S. Abbady ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Pyridine Ring ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Axis Direction ◽  
Title Molecule

In the title molecule, C21H20N2O3S, the styryl and ester substituents are displaced to opposite sides of the plane of the pyridine ring. In the crystal, C—H...O hydrogen bonds form chains extending parallel to the a-axis direction, which pack with partial intercalation of the styryl and ester substituents. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H...H (43.6%), C...H/H...C (15.6%), O...H/H...O (14.9%) and N...H/H...N (11.2%) contacts.

scholarly journals Crystal structure, Hirshfeld surface analysis and contact enrichment ratios of 1-(2,7-dimethylimidazo[1,2-a]pyridin-3-yl)-2-(1,3-dithiolan-2-ylidene)ethanone monohydrate

2019 ◽  
Vol 75 (12) ◽  
pp. 1934-1939 ◽  
Author(s):  
Yvon Bibila Mayaya Bisseyou ◽  
Mahama Ouattara ◽  
Pénétjiligué Adama Soro ◽  
R. C. A. Yao-Kakou ◽  
Abodou Jules Tenon
Keyword(s):  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Enrichment Ratio ◽  
Water Molecules ◽  
Hybrid Compound ◽  
Compound C ◽  
Hybrid Molecules

In the title hydrated hybrid compound C14H14N2OS2·H2O, the planar imidazo[1,2-a]pyridine ring system is linked to the 1,3-dithiolane moiety by an enone bridge. The atoms of the C—C bond in the 1,3-dithiolane ring are disordered over two positions with occupancies of 0.579 (14) and 0.421 (14) and both disordered rings adopt a half-chair conformation. The oxygen atom of the enone bridge is involved in a weak intramolecular C—H...O hydrogen bond, which generates an S(6) graph-set motif. In the crystal, the hybrid molecules are associated in R 2 2(14) dimeric units by weak C—H...O interactions. O—H...O hydrogen bonds link the water molecules, forming infinite self-assembled chains along the b-axis direction to which the dimers are connected via O—H...N hydrogen bonding. Analysis of intermolecular contacts using Hirshfeld surface analysis and contact enrichment ratio descriptors indicate that hydrogen bonds induced by water molecules are the main driving force in the crystal packing formation.

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

2019 ◽  
Vol 75 (2) ◽  
pp. 237-241 ◽  
Author(s):  
Zeliha Atioğlu ◽  
Mehmet Akkurt ◽  
Namiq Q. Shikhaliyev ◽  
Gulnar T. Suleymanova ◽  
Khanim N. Bagirova ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Benzene Ring ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Ring Form ◽  
Compound C

In the title compound, C14H8Cl2FN3O2, the 4-fluorophenyl ring and the nitro-substituted benzene ring form a dihedral angle of 63.29 (8)°. In the crystal, molecules are linked by C—H...O hydrogen bonds into chains running parallel to the c axis. The crystal packing is further stabilized by C—Cl...π, C—F...π and N—O...π interactions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...O/O...H (15.5%), H...H (15.3%), Cl...H/H...Cl (13.8%), C...H/H...C (9.5%) and F...H/H...F (8.2%) interactions.

scholarly journals Crystal structure and Hirshfeld surface analysis of N,N′-[ethane-1,2-diylbis(oxy)]bis(4-methylbenzenesulfonamide)

2019 ◽  
Vol 75 (1) ◽  
pp. 81-85
Author(s):  
Seher Meral ◽  
Sevgi Kansiz ◽  
Necmi Dege ◽  
Aysen Alaman Agar ◽  
Galyna G. Tsapyuk
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Rotation Axis ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Two Dimensional ◽  
Compound C ◽  
Supramolecular Chains

In the molecule of the title compound, C16H20N2O6S2, the mid-point of the C—C bond of the central ethane moiety is located on a twofold rotation axis. In the crystal, molecules are linked by N—H...O hydrogen bonds into supramolecular chains propagating along the [101] direction. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (43.1%), O...H/H...O (40.9%), C...H/H...C (8.8%) and C...C (5.5%) interactions.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy calculation of 1-decyl-2,3-dihydro-1H-benzimidazol-2-one

2021 ◽  
Vol 77 (5) ◽  
pp. 559-563
Author(s):  
Younesse Ait Elmachkouri ◽  
Asmaa Saber ◽  
Ezaddine Irrou ◽  
Bushra Amer ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Dimensional Structure ◽  
Energy Calculation ◽  
Model C ◽  
Hydrogen Bond Energies

The title molecule, C17H26N2O, adopts an L-shaped conformation, with the straight n-decyl chain positioned nearly perpendicular to the dihydrobenzimidazole moiety. The dihydrobenzimidazole portion is not quite planar as there is a dihedral angle of 1.20 (6)° between the constituent planes. In the crystal, N—H...O hydrogen bonds form inversion dimers, which are connected into the three-dimensional structure by C—H...O hydrogen bonds and C—H...π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (75.9%), H...C/C...H (12.5%) and H...O/O...H (7.0%) interactions. Based on computational chemistry using the CE–B3LYP/6–31 G(d,p) energy model, C—H...O hydrogen bond energies are −74.9 (for N—H...O) and −42.7 (for C—H...O) kJ mol−1.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 3-{(2Z)-2-[(2,4-dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl}propanenitrile

2019 ◽  
Vol 75 (6) ◽  
pp. 721-727 ◽  
Author(s):  
Nada Kheira Sebbar ◽  
Brahim Hni ◽  
Tuncer Hökelek ◽  
Abdelhakim Jaouhar ◽  
Mohamed Labd Taha ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Boat Conformation ◽  
Compound C

The title compound, C18H12Cl2N2OS, consists of a dihydrobenzothiazine unit linked by a –CH group to a 2,4-dichlorophenyl substituent, and to a propanenitrile unit is folded along the S...N axis and adopts a flattened-boat conformation. The propanenitrile moiety is nearly perpendicular to the mean plane of the dihydrobenzothiazine unit. In the crystal, C—HBnz...NPrpnit and C—HPrpnit...OThz (Bnz = benzene, Prpnit = propanenitrile and Thz = thiazine) hydrogen bonds link the molecules into inversion dimers, enclosing R 2 2(16) and R 2 2(12) ring motifs, which are linked into stepped ribbons extending along [110]. The ribbons are linked in pairs by complementary C=O...Cl interactions. π–π contacts between the benzene and phenyl rings, [centroid–centroid distance = 3.974 (1) Å] may further stabilize the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (23.4%), H...Cl/Cl...H (19.5%), H...C/C...H (13.5%), H...N/N...H (13.3%), C...C (10.4%) and H...O/O...H (5.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry calculations indicate that the two independent C—HBnz...NPrpnit and C—HPrpnit...OThz hydrogen bonds in the crystal impart about the same energy (ca 43 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.

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