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

ABSTRACT: 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%).

SUBMITTER: Atioglu Z

PROVIDER: S-EPMC8423015 | biostudies-literature |

REPOSITORIES: biostudies-literature

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

Project description: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.

| S-EPMC8647749 | biostudies-literature

(E)-4-{[2-(2-Furylcarbon-yl)hydrazinyl-idene]meth-yl}-2-meth-oxy-phenyl acetate.

Project description:The mol-ecule of the title Schiff base compound, C(15)H(14)N(2)O(5), was obtained from a condensation reaction of 4-acet-oxy-3-meth-oxy-benzaldehyde and 2-furyl-carbonyl-hydrazide. In the mol-ecule, the furyl ring makes a dihedral angle of 14.63 (10)° with the benzene ring. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into chains along the b axis. Futhermore, weak C-H⋯O inter-actions connect the chains, forming corrugated layers parallel to (001). The dihedral angle between the rings is 14.63 (10)°.

| S-EPMC3099912 | biostudies-literature

Synthesis, crystal structure and Hirshfeld surface analysis of 2-chloro-3-[(<i>E</i>)-(2-phenyl-hydrazinyl-idene)meth-yl]quinoline.

Project description:A new quinoline-based hydrazone, C16H12ClN3, was synthesized by a condensation reaction of 2-chloro-3-formyl-quinoline with phenyl-hydrazine. The quinoline ring system is essentially planar (r.m.s. deviation = 0.012?Å), and forms a dihedral angle of 8.46?(10)° with the phenyl ring. The mol-ecule adopts an E configuration with respect to the central C=N bond. In the crystal, mol-ecules are linked by a C-H??-phenyl inter-action, forming zigzag chains propagating along the [10] direction. The N-H hydrogen atom does not participate in hydrogen bonding but is directed towards the phenyl ring of an adjacent mol-ecule, so linking the chains via weak N-H?? inter-actions to form of a three-dimensional structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H?H (35.5%), C?H/H?C (33.7%), Cl?H/H?Cl (12.3%), N?H/H?N (9.5%) contacts.

| S-EPMC6659329 | biostudies-literature

1-Chloro-1-[(4-meth-oxy-phen-yl)hydrazinyl-idene]propan-2-one.

Project description:The non-H atoms of the title compound, C(10)H(11)ClN(2)O(2), lie nearly on a plane (r.m.s. deviation = 0.150?Å), and the C=N double bond has a Z configuration. In the crystal, adjacent mol-ecules are linked by an N-H?O(carbon-yl) hydrogen bond, forming a chain running along [201].

| S-EPMC3212343 | biostudies-literature

Crystal structure of 2-(5-meth-oxy-1-benzo-furan-3-yl)acetic acid.

Project description:The benzo-furan residue in the title compound, C11H10O4, is essentially planar (the r.m.s. deviation for the nine non-H atoms = 0.011 Å). While the meth-oxy group is coplanar with the fused ring system [C-C-O-C torsion angle = 3.1 (3)°], the acetic acid residue occupies a position almost prime [C-C-C-C = 77.0 (2)°]. In the crystal, centrosymmetrically related mol-ecules are linked by O-H⋯O hydrogen bonds to form eight-membered {⋯HOCO}2 synthons. The dimeric aggregates assemble into supra-molecular layers in the ab plane via benzene-C-H⋯O(ring) inter-actions.

| S-EPMC4719975 | biostudies-literature

5-(Biphenyl-4-yl)-3-(3-meth-oxy-benzyl-idene)furan-2(3H)-one.

Project description:In the title compound, C(24)H(18)O(3), the dihedral angles between the mean planes of the five-membered furan ring and the meth-oxy-substituted benzene and the adjacent and outer biphenyl benzene rings are 2.43 (7), 4.48 (7) and 30.47 (8)°, respectively. The crystal packing is stabilized by weak C-H⋯O and C-H⋯π inter-molecular hydrogen bonds and π-π stacking inter-actions [centroid-centroid distances = 3.8752 (8) and 3.8331 (8) Å].

| S-EPMC3200951 | biostudies-literature

(Z)-3-Hydrazinyl-idene-1-phenyl-indolin-2-one.

Project description:The indoline fused-ring system of the title Schiff base, C(14)H(11)N(3)O, is planar (r.m.s. deviation = 0.005?Å); the phenyl substituent is aligned at 66.5?(1)° with respect to the ring system. The amino -NH(2) unit forms an intra-molecular hydrogen bond with the carbonyl O atom. Mol-ecules are connected by an inter-molecular N-H?N hydrogen bond, generating a zigzag chain that runs along the short c axis of the unit cell.

| S-EPMC3009040 | biostudies-literature

2-[(4-Chloro-phen-yl)sulfan-yl]-2-meth-oxy-1-phenyl-ethan-1-one: crystal structure and Hirshfeld surface analysis.

Project description:The title compound, C15H13ClO2S, comprises (4-chloro-phen-yl)sulfanyl, benzaldehyde and meth-oxy residues linked at a chiral methine-C atom (the crystal is racemic). A twist in the methine-C-C(carbon-yl) bond [O-C-C-O torsion angle = 19.3?(7)°] leads to a dihedral angle of 22.2?(5)° between the benzaldehyde and methine+meth-oxy residues. The chloro-benzene ring is folded to lie over the O atoms, with the dihedral angle between the benzene rings being 42.9?(2)°. In the crystal, the carbonyl-O atom accepts two C-H?O inter-actions with methyl- and methine-C-H atoms being the donors. The result is an helical supra-molecular chain aligned along the c axis; chains pack with no directional inter-actions between them. An analysis of the Hirshfeld surface points to the important contributions of weak H?H and C?C contacts to the mol-ecular packing.

| S-EPMC5947492 | biostudies-literature

1-(2-Meth-oxy-phen-yl)-2-{[2-(2-meth-oxy-phen-yl)hydrazinyl-idene](nitro)-meth-yl}diazene.

Project description:In the title compound, C(15)H(15)N(5)O(4), a nitro-formazan derivative, the formazan unit is essentially planar with an r.m.s. deviation of 0.0204?(6)?Å and adopts a closed syn,s-cis configuration with an intra-molecular N-H?N hydrogen bond. The formazan plane makes dihedral angles of 4.32?(5) and 24.35?(5)° with the benzene rings. The dihedral angle between the formazan plane and the nitro group is 12.58?(8)°. In the crystal, C-H?O inter-actions connect the mol-ecules into an inversion dimer.

| S-EPMC3295411 | biostudies-literature

Crystal structure of (3E)-5-nitro-3-(2-phenyl-hydrazinyl-idene)-1H-indol-2(3H)-one.

Project description:The reaction between 5-nitro-isatin and phenyl-hydrazine in acidic ethanol yields the title compound, C14H10N4O3, whose mol-ecular structure deviates slightly from a planar geometry (r.m.s. deviation = 0.065?Å for the mean plane through all non-H atoms). An intra-molecular N-H?O hydrogen bond is present, forming a ring of graph-set motif S(6). In the crystal, mol-ecules are linked by N-H?O and C-H?O hydrogen-bonding inter-actions into a two-dimensional network along (120), and rings of graph-set motif R22(8), R22(26) and R44(32) are observed. Additionally, a Hirshfeld surface analysis suggests that the mol-ecules are stacked along [100] through C=O?Cg inter-actions and indicates that the most important contributions for the crystal structure are O?H (28.5%) and H?H (26.7%) inter-actions. An in silico evaluation of the title compound with the DHFR enzyme (di-hydro-folate reductase) was performed. The isatin-hydrazone derivative and the active site of the selected enzyme show N-H?O(ASP29), N-H?O(ILE96) and Cg?Cg(PHE33) inter-actions.

| S-EPMC5290558 | biostudies-literature

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