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.

scholarly journals Crystal structure and Hirshfeld surface analysis of 2-{[7-acetyl-8-(4-chlorophenyl)-4-cyano-6-hydroxy-1,6-dimethyl-5,6,7,8-tetrahydroisoquinolin-3-yl]sulfanyl}-N-(4-chlorophenyl)acetamide

2021 ◽  
Vol 77 (5) ◽  
pp. 527-531
Author(s):  
Mehmet Akkurt ◽  
Islam S. Marae ◽  
Joel T. Mague ◽  
Shaaban K. Mohamed ◽  
Etify A. Bakhite ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Boat Conformation ◽  
Cyclohexene Ring ◽  
Title Molecule ◽  
Twist Boat

In the title molecule, C28H25Cl2N3O3S, the heterocyclic portion of the tetrahydroisoquinoline unit is planar while the cyclohexene ring adopts a twist-boat conformation. The two 4-chlorophenyl groups extend away from one side of this unit while the hydroxyl and acetyl groups extend away from the opposite side and form an intramolecular O—H...O hydrogen bond. The crystal packing consists of layers parallel to the bc plane. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (37.3%), Cl...H/H...Cl (17.6%), O...H/H...O (11.1%), C...H/H...C (10.9%) and N...H/H...N (9.7%) interactions.

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 Synthesis, crystal structure and Hirshfeld surface analysis of bis{2-[(pyridin-2-yl)amino]pyridinium} tetracyanonickelate(II)

2020 ◽  
Vol 76 (11) ◽  
pp. 1794-1798
Author(s):  
Zouaoui Setifi ◽  
Hela Ferjani ◽  
Fatima Setifi ◽  
Safa Ezzine ◽  
Mohammed Hadi Al-Douh
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bond ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Stacking Interactions ◽  
Two Dimensional ◽  
Molecular Salt

In the title molecular salt, (C10H10N3)2[Ni(CN)4], the dihedral angle between the pyridine rings in the cation is 1.92 (13)° and the complete anion is generated by a crystallographic centre of symmetry. An intramolecular N—H...N hydrogen bond occurs in the cation, which closes an S(6) ring. In the crystal, the components are linked by N—H...N and weak C—H...N hydrogen bonds, which generate chains propagating in the [101] direction. Weak aromatic π–π stacking interactions are also observed. A Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contact types in the crystal packing are N...H/H...N, C...H/H...C and H...H with contributions of 37.2, 28.3 and 21.9%, respectively.

scholarly journals Crystal structure and Hirshfeld surface analysis of (E)-2-(2,4,6-trimethylbenzylidene)-3,4-dihydronaphthalen-1(2H)-one

2019 ◽  
Vol 75 (6) ◽  
pp. 746-750
Author(s):  
Cemile Baydere ◽  
Merve Taşçı ◽  
Necmi Dege ◽  
Mustafa Arslan ◽  
Yusuf Atalay ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Flat Surface ◽  
Crystal Packing ◽  
Shape Index ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Stacking Interactions ◽  
Two Dimensional ◽  
Surface Patches ◽  
Π Stacking

A novel chalcone, C20H20O, derived from benzylidenetetralone, was synthesized via Claissen–Schmidt condensation between tetralone and 2,4,6-trimethylbenzaldehyde. In the crystal, molecules are linked by C—H...O hydrogen bonds, producing R 2 2(20) and R 2 4(12) ring motifs. In addition, weak C—H...π and π-stacking interactions are observed. The intermolecular interactions were investigated using Hirshfeld surface analysis and two-dimensional fingerprint plots, revealing that the most important contributions for the crystal packing are from H...H (66.0%), H...C/ C...H (22.3%), H...O/O...H (9.3%), and C...C (2.4%) interactions. Shape-index plots show π–π stacking interactions and the curvedness plots show flat surface patches characteristic of planar stacking.

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.

scholarly journals Crystal structure and Hirshfeld surface analysis of 6-((E)-2-{4-[2-(4-chlorophenyl)-2-oxoethoxy]phenyl}ethenyl)-4,5-dihydropyridazin-3(2H)-one

2022 ◽  
Vol 78 (1) ◽  
Author(s):  
Said Daoui ◽  
Israa Muwafaq ◽  
Emine Berrin Çınar ◽  
Abdulmalik Abudunia ◽  
Necmi Dege ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Dihedral Angles ◽  
Boat Conformation ◽  
Compound C ◽  
Pyridazine Ring ◽  
Centrosymmetric Dimers

The pyridazine ring in the title compound, C20H17ClN2O3, adopts a screw-boat conformation. The whole molecule is flattened, the dihedral angles subtended by the least-squares plane of the central aromatic ring with those of the terminal benzene and pyridazine rings being 15.18 (19) and 11.23 (19)°, respectively. In the crystal, the molecules are linked by pairs of N—H...O bonds into centrosymmetric dimers and by C—H...π contacts into columns. The results of the Hirshfeld surface analysis show that the most prominent interactions are H...H, accounting for 36.5% of overall crystal packing, and H...O/O...H (18.6% contribution) contacts.

scholarly journals Crystal structure, Hirshfeld surface analysis, interaction energy and DFT studies of (2Z)-2-(2,4-dichlorobenzylidene)-4-nonyl-3,4-dihydro-2H-1,4-benzothiazin-3-one

2020 ◽  
Vol 76 (2) ◽  
pp. 281-287 ◽  
Author(s):  
Brahim Hni ◽  
Nada Kheira Sebbar ◽  
Tuncer Hökelek ◽  
Achour Redouane ◽  
Joel T. Mague ◽  
...  
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, C24H27Cl2NOS, contains 1,4-benzothiazine and 2,4-dichlorophenylmethylidene units in which the dihydrothiazine ring adopts a screw-boat conformation. In the crystal, intermolecular C—HBnz...OThz (Bnz = benzene and Thz = thiazine) hydrogen bonds form chains of molecules extending along the a-axis direction, which are connected to their inversion-related counterparts by C—HBnz...ClDchlphy (Dchlphy = 2,4-dichlorophenyl) hydrogen bonds and C—HDchlphy...π (ring) interactions. These double chains are further linked by C—HDchlphy...OThz hydrogen bonds, forming stepped layers approximately parallel to (012). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (44.7%), C...H/H...C (23.7%), Cl...H/H...Cl (18.9%), O...H/H...O (5.0%) and S...H/H...S (4.8%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, C—HDchlphy...OThz, C—HBnz...OThz and C—HBnz...ClDchlphy hydrogen-bond energies are 134.3, 71.2 and 34.4 kJ mol−1, respectively. 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. The two carbon atoms at the end of the nonyl chain are disordered in a 0.562 (4)/0.438 (4) ratio.

scholarly journals Crystal structure and Hirshfeld surface analysis of 1-[(1-butyl-1H-1,2,3-triazol-4-yl)methyl]-3-methylquinoxalin-2(1H)-one

2018 ◽  
Vol 74 (12) ◽  
pp. 1815-1820
Author(s):  
Nadeem Abad ◽  
Youssef Ramli ◽  
Tuncer Hökelek ◽  
Nada Kheira Sebbar ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Triazole Ring ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Stacking Interactions ◽  
Ring Plane ◽  
Compound C ◽  
Centroid Distance

The title compound, C16H19N5O, is built up from a planar quinoxalinone ring system linked through a methylene bridge to a 1,2,3-triazole ring, which in turn carries ann-butyl substituent. The triazole ring is inclined by 67.09 (4)° to the quinoxalinone ring plane. In the crystal, the molecules form oblique stacks along thea-axis direction through intermolecular C—HTrz...NTrz(Trz = triazole) hydrogen bonds, and offset π-stacking interactions between quinoxalinone rings [centroid–centroid distance = 3.9107 (9) Å] and π–π interactions, which are associated pairwise by inversion-related C—HDhydqn...π(ring) (Dhydqn = dihydroquinoxaline) interactions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (52.7%), H...N/N...H (18.9%) and H...C/C...H (17.0%) 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.

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