Comparison of the crystal structures and Hirshfeld surface analysis of five N-(4-methylbenzenesulfonyl)glycine hydrazone derivatives

2018 ◽  
Vol 74 (11) ◽  
pp. 1553-1560
Author(s):  
H. Purandara ◽  
Sabine Foro ◽  
B. Thimme Gowda
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Surface Analysis ◽  
Hirshfeld Surface ◽  
Amide Group ◽  
Hirshfeld Surface Analysis ◽  
Torsion Angles ◽  
Fingerprint Plots ◽  
Ring Motif ◽  
Bonding Patterns

The crystal structures of N-(4-methylbenzenesulfonyl)glycine hydrazone and four derivatives with four different substituents have been investigated, namely, (E)-N-{2-[2-(benzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H17N3O3S, (I), (E)-N-{2-[2-(4-bromobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16BrN3O3S, (II), (E)-N-{2-[2-(4-chlorobenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C16H16ClN3O3S, (III), (E)-N-(2-{2-[4-(dimethylamino)benzylidene]hydrazinyl}-2-oxoethyl)-4-methylbenzenesulfonamide, C18H22N4O3S, (IV), and (E)-N-{2-[2-(4-methoxybenzylidene)hydrazinyl]-2-oxoethyl}-4-methylbenzenesulfonamide, C17H19N3O4S, (V). The molecules in all five crystal structures show similar conformations and hydrogen-bonding patterns. The central part of the molecule, i.e. C—C—N—N=C, is almost linear in all the structures, with the C—C—N—N torsion angles ranging from −178.3 (1) to −180.0 (2)° and the C—N—N=C torsion angles ranging from −178.5 (4) to −179.8 (3)°. The conformation of the N—H and C=O bonds in the amide group of the hydrazone part is syn in all the compounds. In all the structures, sulfonamide and hydrazone dimers with R 2 2(8) ring motifs are observed, which are further augmented by C—H...O interactions. A common feature of each of (I)–(V) is the formation of sulfonamide and hydrazone dimers with an R 2 2(8) ring motif. Hirshfeld surface analyses gave fingerprint plots for H...H, O...H/H...O, N...H/H...N, C...H/H...C and other contacts. The H...H contacts show large surfaces, whereas the O...H plots show the presence of O...H/O...H contacts with the two characteristic long sharp spikes.

scholarly journals Hirshfeld surface analysis and crystal structure of N-(2-methoxyphenyl)acetamide

2019 ◽  
Vol 75 (6) ◽  
pp. 830-833
Author(s):  
Mavise Yaman ◽  
Necmi Dege ◽  
Mzgin M. Ayoob ◽  
Awaz J. Hussein ◽  
Mohammed K. Samad ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Amide Group ◽  
Hirshfeld Surface Analysis ◽  
Two Dimensional ◽  
Torsion Angles ◽  
Compound C ◽  
Unexpected Product

The title compound, C9H11NO2, was obtained as unexpected product from the reaction of (4-{2-benzyloxy-5-[(E)-(3-chloro-4-methylphenyl)diazenyl]benzylidene}-2-phenyloxazol-5(4H)-one) with 2-methoxyaniline in the presence of acetic acid as solvent. The amide group is not coplanar with the benzene ring, as shown by the C—N—C—O and C—N—C—C torsion angles of −2.5 (3) and 176.54 (19)°, respectively. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H...H (53.9%), C...H/H...C (21.4%), O...H/H...O (21.4%) and N...H/H...N (1.7%) interactions.

scholarly journals Two dialkylammonium salts of 2-amino-4-nitrobenzoic acid: crystal structures and Hirshfeld surface analysis

2016 ◽  
Vol 72 (12) ◽  
pp. 1691-1699 ◽  
Author(s):  
James L. Wardell ◽  
Mukesh M. Jotani ◽  
Edward R. T. Tiekink
Keyword(s):  
Hydrogen Bonding ◽  
Hydrogen Bonds ◽  
Crystal Structures ◽  
Surface Analysis ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Dihedral Angles ◽  
Asymmetric Unit ◽  
Nitrobenzoic Acid ◽  
Ammonium N

The crystal structures of two ammonium salts of 2-amino-4-nitrobenzoic acid are described, namely dimethylazanium 2-amino-4-nitrobenzoate, C2H8N+·C7H5N2O4−, (I), and dibutylazanium 2-amino-4-nitrobenzoate, C8H20N+·C7H5N2O4−, (II). The asymmetric unit of (I) comprises a single cation and a single anion. In the anion, small twists are noted for the carboxylate and nitro groups from the ring to which they are connected, as indicated by the dihedral angles of 11.45 (13) and 3.71 (15)°, respectively; the dihedral angle between the substituents is 7.9 (2)°. The asymmetric unit of (II) comprises two independent pairs of cations and anions. In the cations, different conformations are noted in the side chains in that three chains have an all-trans[(+)-antiperiplanar] conformation, while one has a distinctive kink resulting in a (+)-synclinal conformation. The anions, again, exhibit twists with the dihedral angles between the carboxylate and nitro groups and the ring being 12.73 (6) and 4.30 (10)°, respectively, for the first anion and 8.1 (4) and 12.6 (3)°, respectively, for the second. The difference between anions in (I) and (II) is that in the anions of (II), the terminal groups are conrotatory, forming dihedral angles of 17.02 (8) and 19.0 (5)°, respectively. In each independent anion of (I) and (II), an intramolecular amino-N—H...O(carboxylate) hydrogen bond is formed. In the crystal of (I), anions are linked into a jagged supramolecular chain by charge-assisted amine-N—H...O(carboxylate) hydrogen bonds and these are connected into layersviacharge-assisted ammonium-N—H...O(carboxylate) hydrogen bonds. The resulting layers stack along theaaxis, being connected by nitro-N—O...π(arene) and methyl-C—H...O(nitro) interactions. In the crystal of (II), the anions are connected into four-ion aggregates by charge-assisted amino-N—H...O(carboxylate) hydrogen bonding. The formation of ammonium-N—H...O(carboxylate) hydrogen bonds, involving all ammonium-N—H and carboxylate O atoms leads to a three-dimensional architecture; additional C—H...O(nitro) interactions contribute to the packing. The Hirshfeld surface analysis confirms the importance of the hydrogen bonding in both crystal structures. Indeed, O...H/H...O interactions contribute nearly 50% to the entire Hirshfeld surface in (I).

Hirshfeld surface analysis of the 1,1′-(ethane-1,2-diyl)dipyridinium dication in two new salts: perchlorate and peroxodisulfate

2014 ◽  
Vol 70 (2) ◽  
pp. 230-235 ◽  
Author(s):  
Mostafa Gholizadeh ◽  
Mehrdad Pourayoubi ◽  
Masoumeh Farimaneh ◽  
Atekeh Tarahhomi ◽  
Michal Dušek ◽  
...  
Keyword(s):  
Crystal Structures ◽  
Surface Analysis ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Inversion Symmetry ◽  
Two Dimensional ◽  
Fingerprint Plots ◽  
Intermolecular Contacts

In the title salts, C12H14N22+·2ClO4−, (I), and C12H14N22+·S2O82−, (II), the dication is organized around an inversion centre located at the centre of the –CH2CH2– bridge and the two pyridine segments areantiwith respect to one another. The peroxodisulfate anion in (II) also exhibits inversion symmetry. Hirshfeld surface analysis shows closely similar Hirshfeld surface shapes for the dications in the two salts, reflecting similar intermolecular contacts and similar conformations. The two-dimensional fingerprint plots (FPs) are quite asymmetric, due to the presence of more than one component (cation and anion). The most striking of the complementary features for each of the FPs of the dications is the broad green spike in the regionde>di, without the presence of a corresponding spike in the regionde<di, reflecting the absence of O...H contacts. Moreover, H...O interactions (51% in the dications of both salts) outnumber other contacts in both crystal structures.

scholarly journals Crystal structure and Hirshfeld surface analysis of a bromochalcone: (E)-1-(3-bromophenyl)-3-(2,6-dichlorophenyl)prop-2-en-1-one

2019 ◽  
Vol 75 (2) ◽  
pp. 264-267
Author(s):  
S. Bindya ◽  
C. S. Chidan Kumar ◽  
S. Naveen ◽  
B. P. Siddaraju ◽  
Ching Kheng Quah ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Two Dimensional ◽  
Axis Direction ◽  
Π Interactions ◽  
Fingerprint Plots ◽  
Intermolecular Contacts ◽  
Ring Motif

In the title chalcone derivative, C15H9BrCl2O, the aryl rings are inclined to each by 14.49 (17)°, and the configuration about the C=C bond is E. There is a short intramolecular C—H...Cl contact present resulting in the formation of an S(6) ring motif. In the crystal, the shortest intermolecular contacts are Cl...O contacts [3.173 (3) Å] that link the molecules to form a 21 helix propagating along the b-axis direction. The helices stack up the short crystallographic a axis, and are linked by offset π–π interactions [intercentroid distance = 3.983 (1) Å], forming layers lying parallel to the ab plane. A quantification of the intermolecular contacts in the crystal were estimated using Hirshfeld surface analysis and two-dimensional fingerprint plots.

scholarly journals Crystal structures, Hirshfeld atom refinements and Hirshfeld surface analyses of tris(4,5-dihydrofuran-2-yl)methylsilane and tris(4,5-dihydrofuran-2-yl)phenylsilane

2020 ◽  
Vol 76 (9) ◽  
pp. 1514-1519
Author(s):  
Anna Krupp ◽  
Eva Rebecca Barth ◽  
Rana Seymen ◽  
Carsten Strohmann
Keyword(s):  
Hydrogen Bonding ◽  
Crystal Structures ◽  
Surface Analysis ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Supramolecular Network ◽  
Two Dimensional ◽  
One Dimensional ◽  
Atom Model ◽  
Hydrogen Bonding Interactions

The title compounds, C13H18O3Si (1) and C18H20O3Si (2), represent functionalizable dihydrofuranylsilanes, which permit substitution by a variety of nucleophiles. The crystal structures of 1 and 2 display weak intermolecular C—H...O hydrogen-bonding interactions (quantified by Hirshfeld surface analysis), leading to a two-dimensional supramolecular network for 1 and a one-dimensional supramolecular network for 2. The crystal structures of 1 and 2 were refined both on the basis of the independent atom model (IAM) and the Hirshfeld atom refinement (HAR) approach, and the results are comparatively discussed.

scholarly journals Crystal structure and Hirshfeld surface analysis of ethyl (E)-4-[(4-hydroxy-3-methoxy-5-nitrobenzylidene)amino]benzoate

2018 ◽  
Vol 74 (8) ◽  
pp. 1079-1082
Author(s):  
Antony Samy Victoria ◽  
Palaniyappan Sivajeyanthi ◽  
Natarajan Elangovan ◽  
Kasthuri Balasubramani ◽  
Thathan Kolochi ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Compound C ◽  
High Propensity ◽  
Benzene Rings ◽  
Schiff Base Compound ◽  
Ring Motif ◽  
Base Compound

The title Schiff base compound, C17H16N2O6, has an E configuration with respect to the C=N bond, with a dihedral angle between the two benzene rings of 31.90 (12)°. There is an intramolecular O—H...Onitro hydrogen bond present forming an S(6) ring motif. In the crystal, molecules are linked by pairs of O—H...O hydrogen bonds, forming inversion dimers enclosing an R 2 2(4) ring motif. The dimers are linked about an inversion centre by pairs of C—H...O hydrogen bonds, which enclose R 2 2(22) loops, forming chains propagating along the [10\overline{3}] direction. Hirshfeld surface analysis and fingerprint plots show enrichment ratios for the H...H, O...H and C...H contacts, indicating a high propensity of such interactions in the crystal. Both the nitro group and the CH3–CH2–O– group are positionally disordered.

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