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

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.

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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]

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989019014038 ◽

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%).

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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

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989018015219 ◽

2018 ◽

Vol 74 (12) ◽

pp. 1746-1750 ◽

Cited By ~ 3

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.

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

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989019003700 ◽

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.

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Synthesis, crystallographic analysis and Hirshfeld surface analysis of 4-bromo-2-{[2-(5-bromo-2-nitrophenyl)hydrazin-1-ylidene]methyl}-5-fluorophenol

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989018014627 ◽

2018 ◽

Vol 74 (11) ◽

pp. 1628-1632

Author(s):

Mavise Yaman ◽

Ercan Aydemir ◽

Necmi Dege ◽

Erbil Agar ◽

Turganbay S. Iskenderov

Keyword(s):

Hydrogen Bonds ◽

Dihedral Angle ◽

Surface Analysis ◽

Title Compound ◽

Crystal Packing ◽

Crystallographic Analysis ◽

Hirshfeld Surface ◽

Hirshfeld Surface Analysis ◽

Compound C ◽

Benzene Rings

The title compound, C13H8Br2FN3O3, is nearly planar with a dihedral angle of 10.6 (4)° between the two benzene rings. Intramolecular N—H...O and O—H...N hydrogen bonds occur. In the crystal, the molecules are linked by weak C—H...O and C—H...Br hydrogen bonds. The roles of the intermolecular interactions in the crystal packing were clarified using Hirshfeld surface analysis.

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Crystal structure and Hirshfeld surface analysis of 1-(4-chlorophenyl)-2-{[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]sulfanyl}ethanone

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989017003978 ◽

2017 ◽

Vol 73 (4) ◽

pp. 524-527

Author(s):

Rajesh Kumar ◽

Shafqat Hussain ◽

Khalid M. Khan ◽

Shahnaz Perveen ◽

Sammer Yousuf

Keyword(s):

Crystal Structure ◽

Hydrogen Bonding ◽

Surface Analysis ◽

Title Compound ◽

Crystal Packing ◽

Hirshfeld Surface ◽

Hirshfeld Surface Analysis ◽

Dihedral Angles ◽

Compound C ◽

Benzene Rings

In the title compound, C16H10Cl2N2O2S, the dihedral angles formed by the chloro-substituted benzene rings with the central oxadiazole ring are 6.54 (9) and 6.94 (8)°. In the crystal, C—H...N hydrogen bonding links the molecules into undulating ribbons running parallel to thebaxis. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are the H...C (18%), H...H (17%), H...Cl (16.6%), H...O (10.4%), H...N (8.9%) and H...S (5.9%) interactions.

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

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989019000707 ◽

2019 ◽

Vol 75 (2) ◽

pp. 237-241 ◽

Cited By ~ 10

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.

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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

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989021002358 ◽

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.

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Crystal structure, Hirshfeld surface analysis and computational study of 2-chloro-N-[4-(methylsulfanyl)phenyl]acetamide

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989020002960 ◽

2020 ◽

Vol 76 (4) ◽

pp. 594-598

Author(s):

Sitthichok Mongkholkeaw ◽

Apisit Songsasen ◽

Tanwawan Duangthongyou ◽

Kittipong Chainok ◽

Songwut Suramitr ◽

...

Keyword(s):

Surface Analysis ◽

Title Compound ◽

Crystal Packing ◽

Computational Study ◽

Dft Method ◽

Hirshfeld Surface ◽

Basis Set ◽

Hirshfeld Surface Analysis ◽

Compound C ◽

Out Of Plane

In the title compound, C9H10ClNOS, the amide functional group –C(=O)NH– adopts a trans conformation with the four atoms nearly coplanar. This conformation promotes the formation of a C(4) hydrogen-bonded chain propagating along the [010] direction. The central part of the molecule, including the six-membered ring, the S and N atoms, is fairly planar (r.m.s. deviation of 0.014). The terminal methyl group and the C(=O)CH2 group are slightly deviating out-of-plane while the terminal Cl atom is almost in-plane. Hirshfeld surface analysis of the title compound suggests that the most significant contacts in the crystal are H...H, H...Cl/Cl...H, H...C/C...H, H...O/O...H and H...S/S...H. π–π interactions between inversion-related molecules also contribute to the crystal packing. DFT calculations have been performed to optimize the structure of the title compound using the CAM-B3LYP functional and the 6–311 G(d,p) basis set. The theoretical absorption spectrum of the title compound was calculated using the TD–DFT method. The analysis of frontier orbitals revealed that the π–π* electronic transition was the major contributor to the absorption peak in the electronic spectrum.

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Crystal structure and Hirshfeld surface analysis of 4-{[(E)-4-(heptyloxy)benzylidene]amino}-N-(naphthalen-2-yl)-1,3-thiazol-2-amine

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989020007951 ◽

2020 ◽

Vol 76 (7) ◽

pp. 1092-1095

Author(s):

Ropak A. Sheakh Mohamad ◽

Hashim J. Aziz ◽

Wali M. Hamad

Keyword(s):

Crystal Structure ◽

Dihedral Angle ◽

Surface Analysis ◽

Torsion Angle ◽

Crystal Packing ◽

Hirshfeld Surface ◽

Hirshfeld Surface Analysis ◽

Thiazole Ring ◽

Torsion Angles ◽

Compound C

In the title compound, C27H28N2OS, the naphthalene unit is planar to within 0.015 (2) Å and makes a dihedral angle of 14.24 (16)° with the thiazole ring. The anisole ring is inclined to the thiazole ring by a dihedral angle of 13.18 (23)°. The torsion angle between the heptyl chain and the anisole ring is 61.1 (4)°. These dihedral and torsion angles render the molecule non-planar. In the crystal, molecules are linked by C—H...π interactions, forming zigzag chains that propagate parallel to the b axis. The roles of the various intermolecular interactions in the crystal packing were clarified by Hirshfeld surface analysis; the most important contributions are from H...H (51.5%) and C...H/H...C (31.8%) contacts.

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Synthesis, crystal structure and Hirshfeld surface analysis of 5-cyclopropyl-N-(2-hydroxyethyl)-1-(4-methylphenyl)-1H-1,2,3-triazole-4-carboxamide

Acta Crystallographica Section E Crystallographic Communications ◽

10.1107/s2056989021009774 ◽

2021 ◽

Vol 77 (10) ◽

pp. 1043-1047

Author(s):

Nazariy T. Pokhodylo ◽

Yurii Slyvka ◽

Volodymyr Pavlyuk

Keyword(s):

Crystal Structure ◽

Dihedral Angle ◽

Surface Analysis ◽

Title Compound ◽

Triazole Ring ◽

Hirshfeld Surface ◽

Hirshfeld Surface Analysis ◽

Compound C ◽

Activity Screening ◽

The Mean

The title compound, C15H18N4O2, was obtained via a two-step synthesis (Dimroth reaction and amidation) for anticancer activity screening and was selected from a 1H-1,2,3-triazole-4-carboxamide library. The cyclopropyl ring is oriented almost perpendicular to the benzene ring [dihedral angle = 87.9 (1)°], while the dihedral angle between the mean plane of the cyclopropyl ring and that of the triazole ring is 55.6 (1)°. In the crystal, the molecules are linked by O—H...O and C—H...N interactions into infinite ribbons propagating in the [001] direction, which are interconnected by weak C—H...O interactions into layers. The intermolecular interactions were characterized via Hirshfeld surface analysis, which indicated that the largest fingerprint contact percentages are H...H (55.5%), N...H/H...N (15.4%), C...H/H...C (13.2%) and O...H/H...O (12.9%).

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