scholarly journals Crystal structure, Hirshfeld surface analysis, and DFT studies of N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide

2021 ◽  
Vol 12 (4) ◽  
pp. 439-449
Author(s):  
Cemal Koray Ozer ◽  
Ummuhan Solmaz ◽  
Hakan Arslan
Keyword(s):  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Intramolecular Hydrogen Bonds ◽  
Homo And Lumo ◽  
Intramolecular Hydrogen

N-(2-Chlorophenylcarbamothioyl)cyclohexanecarboxamide was characterized by a single crystal X-ray diffraction study. Crystal data for this compound, C14H17ClN2OS; Monoclinic, space group P21/n with Z = 4, a = 5.2385(10) Å, b = 17.902(4) Å, c = 15.021(3) Å, β = 90.86(3)°, V = 1408.5(5) Å3, T = 153(2) K, μ(MoKα) = 0.413 mm-1, Dcalc = 1.400 g/cm3, 9840 reflections measured (7.082° ≤ 2Θ ≤ 50.378°), 2519 unique (Rint = 0.0406, Rsigma = 0.0335) which were used in all calculations. The final R1 was 0.0397 (I > 2σ(I)) and wR2 was 0.0887 (all data). The puckering parameters (q2 = 0.019(3) Å, q3 = 0.578(3) Å, θ = 1.0(3)° and φ = 51(8)°) of the title compound show that the cyclohexane ring adopts a chair conformation. The molecular conformation of the title compound is stabilized by intramolecular hydrogen bonds (N2-H2⋅⋅⋅Cl1, N2-H2⋅⋅⋅O1, and C2-H2A⋅⋅⋅S1) and intermolecular hydrogen bonds (N1-H1⋅⋅⋅S1i and C9-HA⋅⋅⋅S1ii: 2-x, 2-y, 1-z). The intramolecular hydrogen bonds (N2-H2⋅⋅⋅O1 and C2-H2A⋅⋅⋅S1) are also form two pseudo-six-membered rings. Density functional theory optimized structure in the gaseous phase at B3LYP/6-311G(d,p) level of theory has been compared with the experimentally defined molecular structure. The molecular orbitals HOMO and LUMO with the energy gap for the title compound are calculated and the estimated energy gap (ΔE) between the HOMO and LUMO energies levels of the title compound is 3.5399 eV, which implies that the title molecule is very reactive. The Hirshfeld surface analysis reveals that the most important contributions to crystal packing are from H···H (49.0%), H···C/C···H (12.5%), H···Cl/Cl···H (10.9%), and H···S/S···H (10.0%) interactions. The energy-framework calculations are used to analyze and visualize the three-dimensional topology of the crystal packing. The intermolecular energy analysis confirmed a significant contribution of dispersion to the stabilization of molecular packings in the title compound.

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, 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 (3S,3aR,6aS)-3-(1,3-diphenyl-1H-pyrazol-4-yl)-5-(4-methoxyphenyl)-2-phenyl-3,3a,4,5,6,6a-hexahydro-2H-pyrrolo[3,4-d][1,2]oxazole-4,6-dione

2021 ◽  
Vol 77 (4) ◽  
pp. 356-359
Author(s):  
Shaaban K. Mohamed ◽  
Awad I. Said ◽  
Joel T. Mague ◽  
Talaat I. El-Emary ◽  
Mehmet Akkurt ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Compound C ◽  
Chiral Carbon

In the title compound, C33H26N4O4, the two fused five-membered rings and their N-bound aromatic substituents form a pincer-like motif. The relative conformations about the three chiral carbon atoms are established. In the crystal, a combination of C—H...O and C—H...N hydrogen bonds and C—H...π(ring) interactions leads to the formation of layers parallel to the bc plane. A Hirshfeld surface analysis indicates that the most significant contributions to the crystal packing are from H...H (44.3%), C...H/H...C (29.8%) and O...H/H...O (15.0%) contacts.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 1-benzyl-3-[(1-benzyl-1H-1,2,3-triazol-5-yl)methyl]-2,3-dihydro-1H-1,3-benzodiazol-2-one monohydrate

2020 ◽  
Vol 76 (1) ◽  
pp. 95-101
Author(s):  
Asmaa Saber ◽  
Nada Kheira Sebbar ◽  
Tuncer Hökelek ◽  
Mohamed Labd Taha ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Close Approach ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Dimensional Structure

In the title molecule, C24H21N5O·H2O, the dihydrobenzodiazole moiety is not quite planar, while the whole molecule adopts a U-shaped conformation in which there is a close approach of the two benzyl groups. In the crystal, chains of alternating molecules and lattice water extending along [201] are formed by O—HUncoordW...ODhyr and O—HUncoordW...NTrz (UncoordW = uncoordinated water, Dhyr = dihydro and Trz = triazole) hydrogen bonds. The chains are connected into layers parallel to (010) by C—HTrz...OUncoordW hydrogen bonds with the dihydrobenzodiazole units in adjacent layers intercalating to form head-to-tail π-stacking [centroid-to-centroid distance = 3.5694 (11) Å] interactions between them, which generates the overall three-dimensional structure. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (52.1%), H...C/C...H (23.8%) and O...H/H...O (11.2%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. 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 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 1-{[2-oxo-3-(prop-1-en-2-yl)-2,3-dihydro-1H-1,3-benzodiazol-1-yl]methyl}-3-(prop-1-en-2-yl)-2,3-dihydro-1H-1,3-benzodiazol-2-one

2018 ◽  
Vol 74 (12) ◽  
pp. 1746-1750 ◽  
Author(s):  
Asmaa Saber ◽  
Nada Kheira Sebbar ◽  
Tuncer Hökelek ◽  
Brahim Hni ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Dihedral Angle ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Compound C ◽  
Hydrogen Bonded

In the title compound, C21H20N4O2, the intramolecular C—H...O hydrogen-bonded benzodiazolone moieties are planar to within 0.017 (1) and 0.026 (1) Å, and are oriented at a dihedral angle of 57.35 (3)°. In the crystal, two sets of intermolecular C—H...O hydrogen bonds generate layers parallel to the bc plane. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (51.8%), H...C/C...H (30.7%) and H...O/O...H (11.2%) interactions.

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 4-aminopyridinium thiocyanate–4-aminopyridine (1/1)

2020 ◽  
Vol 76 (9) ◽  
pp. 1535-1538
Author(s):  
M. Renugadevi ◽  
A. Sinthiya ◽  
Kumaradhas Poomani ◽  
Suganya Suresh
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Compound C

In the crystals of the title compound, C5H7N2 +·CNS−·C5H6N2, the components are linked by three N—H...N and two N—H...S hydrogen bonds, resulting in two interpenetrating three-dimensional networks. Hirshfeld surface analysis shows that the most important contributions to the crystal packing are from H...H (36.6%), C...H/H...C (20.4%), S...H/H...S (19.7%) and N...H/H...N (13.4%) interactions.

scholarly journals Crystal structure and Hirshfeld surface analysis of a new benzodiazepine derivative: 4-dichloromethyl-2,3-dihydro-1H-1,5-benzodiazepin-2-one

2019 ◽  
Vol 75 (1) ◽  
pp. 33-37 ◽  
Author(s):  
Karim Chkirate ◽  
Sevgi Kansiz ◽  
Khalid Karrouchi ◽  
Joel T. Mague ◽  
Necmi Dege ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Compound C ◽  
The Mean ◽  
Ring Motif

In the title compound, C10H8Cl2N2O, the seven-membered diazepine ring adopts a boat-shaped conformation. The mean planes of the two rings of the benzodiazepine unit are inclined to each other by 22.05 (6)°. In the crystal, molecules are linked by pairs of N—H...O hydrogen bonds, forming inversion dimers with anR22(8) ring motif. The dimers are linked by C—H...π interactions, forming layers lying parallel to (10\overline{1}). The roles of the intermolecular interactions in the crystal packing were clarified using Hirshfeld surface analysis; the most important contributions are from Cl...H/H...Cl (30.5%) and H...H (22.5%) interactions.

scholarly journals Crystal structure and Hirshfeld surface analysis of (3Z)-7-methoxy-3-(2-phenylhydrazinylidene)-1-benzofuran-2(3H)-one

2021 ◽  
Vol 77 (9) ◽  
Author(s):  
Zeliha Atioğlu ◽  
Mehmet Akkurt ◽  
Ulviyya F. Askerova ◽  
Sevinc H. Mukhtarova ◽  
Rizvan K. Askerov ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Title Compound ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Stacking Interactions ◽  
Compound C ◽  
Ring Motif

In the title compound, C15H12N2O3, pairs of molecules are linked into dimers by N—H...O hydrogen bonds, forming an R 2 2(12) ring motif, with the dimers stacked along the a axis. These dimers are connected through π–π stacking interactions between the centroids of the benzene and furan rings of their 2,3-dihydro-1-benzofuran ring systems. Furthermore, there exists a C—H...π interaction that consolidates the crystal packing. A Hirshfeld surface analysis indicates that the most important contacts are H...H (40.7%), O...H/H...O (24.7%), C...H/H...C (16.1%) and C...C (8.8%).

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