scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile

2020 ◽  
Vol 76 (8) ◽  
pp. 1195-1200
Author(s):  
Md. Serajul Haque Faizi ◽  
Emine Berrin Cinar ◽  
Alev Sema Aydin ◽  
Erbil Agar ◽  
Necmi Dege ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Condensation Reaction ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Orthorhombic Space Group ◽  
Compound C ◽  
Dimensional Network

The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 2-aminobenzonitrile, and crystallizes in the orthorhombic space group Pbca. The phenol ring is inclined to the benzonitrile ring by 25.65 (3)°. The configuration about the C=N bond is E, stabilized by a strong intramolecular O—H...N hydrogen bond that forms an S(6) ring motif. In the crystal, C—H...O and C—H...N interactions lead to the formation of sheets perpendicular to the a axis. C—H...π interactions, forming polymeric chains along the a-axis direction, connect these sheets into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H...H and C...H/H...C interactions. The density functional theory (DFT) optimized structure at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO–LUMO energy gap is given.

scholarly journals Crystal structure, Hirshfeld surface analysis, interaction energy and DFT studies of 4-[(4-allyl-2-methoxyphenoxy)methyl]-1-(4-methoxyphenyl)-1H-1,2,3-triazole

2020 ◽  
Vol 76 (6) ◽  
pp. 962-966
Author(s):  
Abdelmaoujoud Taia ◽  
Mohamed Essaber ◽  
Abdeljalil Aatif ◽  
Karim Chkirate ◽  
Tuncer Hökelek ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Hydrogen Bond Energy ◽  
Dimensional Network ◽  
Phenyl Rings

In the title molecule, C20H21N3O3, the allyl substituent is rotated out of the plane of its attached phenyl ring [torsion angle 100.66 (15)°]. In the crystal, C—HMthphn...OMthphn (Mthphn = methoxyphenyl) hydrogen bonds lead to the formation of (100) layers that are connected into a three-dimensional network by C—H...π(ring) interactions, together with π–π stacking interactions [centroid-to-centroid distance = 3.7318 (10) Å] between parallel phenyl rings. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (48.7%) and H...C/C...H (23.3%) interactions. Computational chemistry reveals that the C—HMthphn...OMthphn hydrogen bond energy is 47.1 kJ mol−1. The theoretical structure, optimized by density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level, is compared with the experimentally determined molecular structure. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-2-{[(3-chloro-4-methylphenyl)imino]methyl}-4-methylphenol

2020 ◽  
Vol 76 (8) ◽  
pp. 1320-1324
Author(s):  
Md. Serajul Haque Faizi ◽  
Emine Berrin Cinar ◽  
Alev Sema Aydin ◽  
Erbil Agar ◽  
Necmi Dege ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Condensation Reaction ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Monoclinic Space Group ◽  
Compound C ◽  
The Density Functional Theory

The title compound, C15H14ClNO, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 3-chloro-4-methylaniline, and crystallizes in the monoclinic space group P21/c. The 3-chlorobenzene ring is inclined to the phenol ring by 9.38 (11)°. The configuration about the C=N bond is E and an intramolecular O—H...N hydrogen bond forms an S(6) ring motif. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are from H...H (43.8%) and C...H/H...C (26.7%) interactions. The density functional theory (DFT) optimized structure at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO–LUMO energy gap is provided.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)-6-methoxyphenol

2020 ◽  
Vol 76 (5) ◽  
pp. 605-610
Author(s):  
Ballo Daouda ◽  
Nanou Tiéba Tuo ◽  
Tuncer Hökelek ◽  
Kangah Niameke Jean-Baptiste ◽  
Kodjo Charles Guillaume ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C

The title compound, C18H16N2O2, consists of perimidine and methoxyphenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar C4N2 ring adopting an envelope conformation with the NCN group hinged by 47.44 (7)° with respect to the best plane of the other five atoms. In the crystal, O—HPhnl...NPrmdn and N—HPrmdn...OPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Weak C—H...π interactions may further stabilize the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (49.0%), H...C/C...H (35.8%) and H...O/O...H (12.0%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the O—HPhnl...NPrmdn and N—HPrmdn...OPhnl hydrogen-bond energies are 58.4 and 38.0 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.

scholarly journals Crystal structure and Hirshfeld surface analysis of 2-{[(4-iodophenyl)imino]methyl}-4-nitrophenol

2020 ◽  
Vol 76 (7) ◽  
pp. 1146-1149
Author(s):  
Md. Serajul Haque Faizi ◽  
Tenzile Alagöz ◽  
Ruby Ahmed ◽  
Emine Berrin Cinar ◽  
Erbil Agar ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Condensation Reaction ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Orthorhombic Space Group ◽  
Compound C ◽  
Hydrogen Bonding Interactions ◽  
Packing Arrangement ◽  
Phenol Ring

The title compound, C13H9IN2O3, was synthesized by a condensation reaction between 2-hydroxy-5-nitrobenzaldehyde and 4-iodoaniline, and crystallizes in the orthorhombic space group Pna21. The 4-iodobenzene ring is inclined to the phenol ring by a dihedral angle of 39.1 (2)°. The configuration about the C=N double bond is E. The crystal structure features C—H...O hydrogen-bonding interactions. A Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the packing arrangement are O...H/H...O (26.9%) and H...H (22.0%) interactions.

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 3-amino-1-oxo-2,6,8-triphenyl-1,2,7,8-tetrahydroisoquinoline-4-carbonitrile

2021 ◽  
Vol 77 (2) ◽  
pp. 195-199
Author(s):  
Farid N. Naghiyev ◽  
Maria M. Grishina ◽  
Victor N. Khrustalev ◽  
Ali N. Khalilov ◽  
Mehmet Akkurt ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Ring System ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Boat Conformation ◽  
Compound C ◽  
Dimensional Network ◽  
Phenyl Rings

In the title compound, C28H21N3O, the 1,2-dihydropyridine ring of the 1,2,7,8-tetrahydroisoquinoline ring system is planar as expected, while the cyclohexa-1,3-diene ring has a twist-boat conformation, with Cremer–Pople parameters Q T = 0.367 (2) A, θ = 117.3 (3)° and φ = 327.3 (4)°. The dihedral angles between the best planes through the isoquinoline ring system and the three phenyl rings are 81.69 (12), 82.45 (11) and 47.36 (10)°. In the crystal, molecules are linked via N—H...O and C—H...N hydrogen bonds, forming a three-dimensional network. Furthermore, the crystal packing is dominated by C—H...π bonds with a strong interaction involving the phenyl H atoms. The role of the intermolecular interactions in the crystal packing was clarified using Hirshfeld surface analysis, and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (46.0%), C...H/H...C (35.1%) and N...H/H...N (10.5%) contacts.

scholarly journals Crystal structure and Hirshfeld surface analysis of (RS)-3-hydroxy-2-{[(3aRS,6RS,7aRS)-2-(4-methylphenylsulfonyl)-2,3,3a,6,7,7a-hexahydro-3a,6-epoxy-1H-isoindol-6-yl]methyl}isoindolin-1-one

2021 ◽  
Vol 77 (3) ◽  
pp. 260-265
Author(s):  
Dmitriy F. Mertsalov ◽  
Maryana A. Nadirova ◽  
Elena A. Sorokina ◽  
Marina A. Vinokurova ◽  
Sevim Türktekin Çelikesir ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Boat Conformation ◽  
Central Ring ◽  
Compound C ◽  
Dimensional Network ◽  
Phenyl Rings

The title compound, C24H24N2O5S, crystallizes with two independent molecules (A and B) in the asymmetric unit. In the central ring systems of both molecules, the tetrahydrofuran rings adopt envelope conformations, the pyrrolidine rings adopt a twisted-envelope conformation and the six-membered ring is in a boat conformation. In molecules A and B, the nine-membered groups attached to the central ring system are essentially planar (r.m.s. deviations of 0.002 and 0.003 Å, respectively). They form dihedral angles of 64.97 (9) and 56.06 (10)°, respectively, with the phenyl rings. In the crystal, strong intermolecular O—H...O hydrogen bonds and weak intermolecular C—H...O contacts link the molecules, forming a three-dimensional network. In addition weak π–π stacking interactions [centroid-to centroid distance = 3.7124 (13) Å] between the pyrrolidine rings of the nine-membered groups of A molecules are observed. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to quantify the intermolecular interactions present in the crystal, indicating that the environments of the two molecules are very similar. The most important contributions for the crystal packing are from H...H (55.8% for molecule A and 53.5% for molecule B), O...H/H...O (24.5% for molecule A and 26.3% for molecule B) and C...H/H...C (12.6% for molecule A and 15.7% for molecule B) interactions.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 6-bromo-3-(12-bromododecyl)-2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine

2020 ◽  
Vol 76 (5) ◽  
pp. 677-682 ◽  
Author(s):  
Zainab Jabri ◽  
Karim Jarmoni ◽  
Tuncer Hökelek ◽  
Joel T. Mague ◽  
Safia Sabir ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Side Chain ◽  
Functional Theory ◽  
Compound C ◽  
Homo Lumo

The title compound, C24H30Br2N4O2, consists of a 2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine entity with a 12-bromododecyl substituent attached to the pyridine N atom. The middle eight-carbon portion of the side chain is planar to within 0.09 (1) Å and makes a dihedral angle of 21.9 (8)° with the mean plane of the imidazolopyridine moiety, giving the molecule a V-shape. In the crystal, the imidazolopyridine units are associated through slipped π–π stacking interactions together with weak C—HPyr...ONtr and C—HBrmdcyl...ONtr (Pyr = pyridine, Ntr = nitro and Brmdcyl = bromododecyl) hydrogen bonds. The 12-bromododecyl chains overlap with each other between the stacks. The terminal –CH2Br group of the side chain shows disorder over two resolved sites in a 0.902 (3):0.098 (3) ratio. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (48.1%), H...Br/Br...H (15.0%) and H...O/O...H (12.8%) interactions. The optimized molecular structure, using density functional theory at the B3LYP/ 6–311 G(d,p) level, is compared with the experimentally determined 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 ethyl (4R,4aS)-2-methyl-5,8-dioxo-6-phenyl-4a,5,6,7,7a,8-hexahydro-4H-furo[2,3-f]isoindole-4-carboxylate

2021 ◽  
Vol 77 (2) ◽  
pp. 86-90
Author(s):  
Vladimir P. Zaytsev ◽  
Lala V. Chervyakova ◽  
Elena A. Sorokina ◽  
Kirill A. Vasilyev ◽  
Sevim Türktekin Çelikesir ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Three Dimensional ◽  
Chair Conformation ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Pyrrolidine Ring ◽  
Compound C ◽  
Dimensional Network ◽  
Centroid Distance ◽  
Puckering Parameters

In the title compound, C20H19NO5, the central six-membered ring has a slightly distorted half-chair conformation, with puckering parameters of Q T = 0.3387 (11) Å, θ = 49.11 (19)° and φ = 167.3 (2)°. The conformation of the fused pyrrolidine ring is that of an envelope. Molecules are connected by intermolecular C—H...O hydrogen bonds, C—H...π interactions and π–π stacking interactions [centroid-to-centroid distance = 3.9536 (11) Å, with a slippage of 2.047 Å], forming a three-dimensional network. The most important contributions to the surface contacts are from H...H (46.3%), O...H/H...O (31.5%) and C...H/H...C (17.3%) interactions, as concluded from a Hirshfeld surface analysis.

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.

Sign in / Sign up

Export Citation Format

Share Document