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Crystal structure and Hirshfeld surface analysis of 3-[2-(3,5-di-methyl-phen-yl)hydrazinyl-idene]benzo-furan-2(3H)-one.

ABSTRACT: In the title compound, C₁₆H₁₄N₂O₂, the 2,3-di-hydro-1-benzo-furan ring system is essentially planar and makes a dihedral angle of 3.69 (7)° with the di-methyl-phenyl ring. The mol-ecular conformation is stabilized by an intra-molecular N-H⋯O hydrogen bond with an S(6) ring motif. In the crystal, mol-ecules are connected by C-H⋯π and π-π stacking inter-actions, forming a layer lying parallel to the (11) plane. One methyl group is disordered over two orientations, with occupancies of 0.67 (4) and 0.33 (4). Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (51.2%), O⋯H/H⋯O (17.9%), C⋯H/H⋯C (15.2%) and C⋯C (8.1%) contacts.

SUBMITTER: Atioglu Z

PROVIDER: S-EPMC8647749 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structures of isomeric 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)benzene-sulfonamide, 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide.

Project description:The crystal structures of three isomeric compounds of formula C14H13Cl2NO2S, namely 3,5-di-chloro-N-(2,3-di-methyl-phen-yl)-benzene-sulfonamide (I), 3,5-di-chloro-N-(2,6-di-methyl-phen-yl)benzene-sulfonamide (II) and 3,5-di-chloro-N-(3,5-di-methyl-phen-yl)benzene-sulfonamide (III) are described. The mol-ecules of all the three compounds are U-shaped with the two aromatic rings inclined at 41.3 (6)° in (I), 42.1 (2)° in (II) and 54.4 (3)° in (III). The mol-ecular conformation of (II) is stabilized by intra-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions. The crystal structure of (I) features N-H⋯O hydrogen-bonded R22(8) loops inter-connected via C(7) chains of C-H⋯O inter-actions, forming a three-dimensional architecture. The structure also features π-π inter-actions [Cg⋯Cg = 3.6970 (14) Å]. In (II), N-H⋯O hydrogen-bonded R22(8) loops are inter-connected via π-π inter-actions [inter-centroid distance = 3.606 (3) Å] to form a one-dimensional architecture running parallel to the a axis. In (III), adjacent C(4) chains of N-H⋯O hydrogen-bonded mol-ecules running parallel to [010] are connected via C-H⋯π inter-actions, forming sheets parallel to the ab plane. Neighbouring sheets are linked via offset π-π inter-actions [inter-centroid distance = 3.8303 (16) Å] to form a three-dimensional architecture.

| S-EPMC5418781 | biostudies-literature

Crystal structure of N'-[(E)-3,5-di-chloro-2-hy-droxy-benzyl-idene]-4-nitro-benzo-hydrazide di-methyl-formamide monosolvate.

Project description:In the title compound, C14H9Cl2N3O4·C3H7NO, the hydrazone mol-ecule adopts an E conformation with respect to azomethine bond, and the dihedral angle between the two aromatic rings [8.96 (11)°] shows that the rings are almost co-planar. The planar conformation of the mol-ecule is stabilized by the intra-molecular O-H⋯N hydrogen bond involving the OH group and azomethine N atom. The azomethine and keto bond distances [1.269 (2) and 1.210 (2) Å, respectively] are very close to the formal C=N and C=O bond lengths. The di-methyl-formamide solvent mol-ecule is connected to the hydrazone NH group via an N-H⋯O hydrogen bond. In the crystal, non-classical C-H⋯O and C-H⋯Cl hydrogen bonds link the mol-ecules into chains along [322]. A supra-molecular three-dimensional architecture is created by weak C-Cl⋯π [4.163 (3) Å, 83.26 (9)°] and π-π [centroid-centroid distance = 4.0395 (14) Å] inter-actions.

| S-EPMC4645068 | biostudies-literature

Crystal structure of diethyl (E)-2-[(benzo-furan-2-yl)methyl-idene]succinate.

Project description:The title compound, C17H18O5, was synthesized by a base-free catalytic Wittig reaction. The mol-ecule consists of a diethyl itaconate unit, which is connected via the C=C double bond to a benzo-furan moiety. The benzo-furan ring system (r.m.s. deviation = 0.007 Å) forms dihedral angles of 79.58 (4) and 12.12 (10)° with the mean planes through the cis and trans eth-oxy-carbonyl groups, respectively. An intra-molecular C-H⋯O hydrogen bond involving the O atom of the benzo-furan moiety is observed. In the crystal, mol-ecules are linked into ribbons running parallel to the b axis by C-H⋯O hydrogen bonds.

| S-EPMC4645082 | biostudies-literature

(Z)-5-(4-Bromo-phen-yl)-3-{[(3,5-di-chloro-phen-yl)amino]-methyl-idene}furan-2(3H)-one.

Project description:The title compound, C17H10BrCl2NO2, crystallizes in the monoclinic space group C2/c with a large cell volume of 6207 (3) Å3. The asymmetric unit of the title compound investigated at 120 K contains two crystallographically independent mol-ecules (Z' = 2). Each mol-ecule demonstrates slight non-planarity in the solid state and a Z-configuration for the exocyclic C=C bond. The crystal packing reveals the presence of π-π stacking inter-actions between the substituted benzene rings [centroid-centroid distances of 3.836 (5) Å, shift distances in the range 1.272-1.843 Å].

| S-EPMC9462252 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (3Z)-7-meth-oxy-3-(2-phenyl-hydrazinyl-idene)-1-benzo-furan-2(3H)-one.

Project description:In the title compound, C15H12N2O3, pairs of mol-ecules 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 inter-actions between the centroids of the benzene and furan rings of their 2,3-di-hydro-1-benzo-furan ring systems. Furthermore, there exists a C-H⋯π inter-action 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%).

| S-EPMC8423015 | biostudies-literature

(3-Chloro-phen-yl)[(E)-2-(1,3-di-thio-lan-2-yl-idene)hydrazinyl-idene]methyl 3-chloro-benzoate.

Project description:In the title compound, C17H12Cl2N2O2S2, the di-thia-cyclo-pentane ring has an envelope conformation with one of the methyl-ene C atoms as the flap. The chloro-phenyl rings make a dihedral angle of 82.63?(7)°. In the crystal, ?-? inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.547?(2)?Å] link the mol-ecules into inversion dimers. Weak non-classical C-H?X (X = O, N, Cl) inter-actions further consolidate the packing, forming a layer structure parallel to (110).

| S-EPMC3648247 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-1-(3,5-di-chloro-2-hy-droxy-phen-yl)-3-(5-methyl-furan-2-yl)prop-2-en-1-one.

Project description:The title chalcone derivative, C14H10Cl2O3, is almost planar, with a dihedral angle of 7.0?(2) ° between the 3,5-di-chloro-2-hy-droxy-phenyl and 5-methyl-furan rings. There is an intra-molecular O-H?O hydrogen bond present forming an S(6) ring motif. In the crystal, mol-ecules are linked by bifurcated C-H/H?O hydrogen bonds, enclosing an R 1 2(6) ring motif, forming a 21 helix propagating along the b-axis direction. The inter-molecular inter-actions were qu-anti-fied using Hirshfeld surface analysis.

| S-EPMC6176444 | biostudies-literature

Crystal structure of 3-(3,4-di-methyl-anilino)-2-benzo-furan-1(3H)-one.

Project description:In the title compound, C16H15NO2, the 2-benzo-furan-1(3H)-one and 3,4-di-methyl-aniline fragments are oriented with a dihedral angle of 89.12 (5)°. N-H⋯O hydrogen-bond inter-actions join mol-ecules into C(6) chains propagating along the a axis. In addition, there are π-π stacking inter-actions between the 2-benzo-furan-one benzene rings [centroid-centroid dis-tance = 3.7870 (13) Å] and C-H⋯π inter-actions between one of the methyl groups and the 3,4-di-methyl-aniline benzene ring.

| S-EPMC4459309 | biostudies-literature

Crystal structure of 5-(1-benzo-furan-2-yl)-3-(4-methyl-phen-yl)-4,5-di-hydro-1,2-oxazol-5-ol.

Project description:In the title compound, C18H15NO3, the isoxazole moiety adopts a shallow envelope conformation, with the C atom bearing the OH group displaced by 0.148 (1) Å from the mean plane through the other four atoms. The mean plane of this ring (all atoms) subtends dihedral angles of 87.19 (6) and 15.51 (7)° with the benzo-furan ring system (r.m.s. deviation = 0.007 Å) and the 4-methylphenyl ring, respectively. In the crystal, mol-ecules are linked by O-H⋯N hydrogen bonds, generating [001] C(5) chains, with adjacent mol-ecules in the chain related by c-glide symmetry. Weak C-H⋯O inter-actions link the chains into a three-dimensional network.

| S-EPMC4518973 | biostudies-literature

Crystal structure of N'-[4-(di-methyl-amino)-benzyl-idene]furan-2-carbohydrazide monohydrate.

Project description:The condensation of 2-furoic hydrazide and 4-dimethyl amino-benzaldehyde in ethanol yielded a yellow solid formulated as the title compound, C14H15N3O2·H2O. The crystal packing is stabilized by inter-molecular O(water)-H?O,N(carbohydrazide) and N-H?O(water) hydrogen bonds, which form a two-dimensional network along the bc plane. Additional C-H?O inter-actions link the mol-ecules into a three-dimensional network. The dihedral angle between the mean planes of the benzene and the furan ring is 34.47?(6)°. The carbohydrazide moiety, i.e., the C=N-N-C=O fragment and the benzene ring are almost coplanar, with an angle of 6.75?(9)° between their mean planes.

| S-EPMC7199266 | biostudies-literature

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