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Crystal structures of (E)-3-(4-hy-droxy-benzyl-idene)chroman-4-one and (E)-3-(3-hy-droxy-benzyl-idene)-2-phenyl-chroman-4-one.

ABSTRACT: The synthesis and crystal structures of (E)-3-(4-hy-droxy-benzyl-idene)chroman-4-one, C₁₆H₁₂O₃, I, and (E)-3-(3-hy-droxy-benzyl-idene)-2-phenyl-chroman-4-one, C₂₂H₁₆O₃, II, are reported. These compounds are of inter-est with respect to biological activity. Both structures display inter-molecular C-H⋯O and O-H⋯O hydrogen bonding, forming layers in the crystal lattice. The crystal structure of compound I is consolidated by π-π inter-actions. The lipophilicity (logP) was determined as it is one of the parameters qualifying compounds as potential drugs. The logP value for compound I is associated with a larger contribution of C⋯H inter-action in the Hirshfeld surface.

SUBMITTER: Suchojad K

PROVIDER: S-EPMC6895947 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structures of (E)-N'-(2-hy-droxy-5-methyl-benzyl-idene)isonicotinohydrazide and (E)-N'-(5-fluoro-2-hy-droxy-benzyl-idene)isonicotinohydrazide.

Project description:Two derivatives of the well-known iron chelator, (E)-N'-(2-hy-droxy-benzyl-idene)isonicotinohydrazide (SIH), substituted in the 5-position of the 2-hy-droxy-benzene ring by a methyl and a fluorine group viz. (E)-N'-(2-hy-droxy-5-methyl-benzyl-idene)isonicotinohydrazide, C14H13N3O2, (I), and (E)-N'-(5-fluoro-2-hy-droxy-benzyl-idene)isonicotinohydrazide, C13H10FN3O2, (II), have been prepared and characterized by single-crystal X-ray diffraction, (1)H NMR and mass spectrometry. The mol-ecules of both compounds deviate slightly from planarity [r.m.s. deviations are 0.145 and 0.110 Å for (I) and (II), respectively] and adopt an E conformation with respect to the double bond of the hydrazone bridge. In each mol-ecule, there is an intra-molecular O-H⋯N hydrogen bond forming an S(6) ring motif. The dihedral angles between the mean planes of the isonicotinoyl ring and the cresol ring in (I) or the fluoro-phenol ring in (II) are 10.49 (6) and 9.43 (6)°, respectively. In the crystals of both compounds, zigzag chains are formed via N-H⋯N hydrogen bonds, in the [10-1] direction for (I) and [010] for (II). In (I), the chains are linked by weak C-H⋯π and π-π stacking inter-actions [centroid-to-centroid distances = 3.6783 (8) Å; inter-planar angle = 10.94 (5)°], leading to the formation of a three-dimensional supra-molecular architecture. In (II), adjacent chains are connected through C-H⋯O hydrogen bonds to form sheets parallel to (100), which enclose R 4 (4)(30) ring motifs. The sheets are linked by weak C-H⋯π and π-π [centroid-to-centroid distance = 3.7147 (8) Å; inter-planar angle = 10.94 (5)°] inter-actions, forming a three-dimensional supra-molecular architecture.

| S-EPMC4992920 | biostudies-literature

Crystal structure of 4-[(E)-(4-hy-droxy-benzyl-idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one.

Project description:The asymmetric unit of the title compound, C18H17N3O2, comprises three independent mol-ecules (1, 2 and 3). In mol-ecule 1, the dihedral angles between the pyrazolone ring and the pendant phenyl and hydroxybenzene rings are 54.43 (6) and 28.72 (6)°, respectively. The corresponding data for mol-ecule 2 are 86.84 (6) and 25.69 (5)°, respectively, and for mol-ecule 3 are 47.41 (7) and 17.09 (7)°, respectively. The three mol-ecules feature an intra-molecular C-H⋯O inter-action, which closes an S(6) ring in each case. In the crystal, mol-ecules are linked by O-H⋯O hydrogen bonds, which generate [100] chains incorporating all three asymmetric mol-ecules. Two weak C-H⋯O interactions connect three independent molecules to each other along the c-axis direction.

| S-EPMC4719916 | biostudies-literature

Crystal structure of (E)-4-hy-droxy-N'-(3-hy-droxy-benzyl-idene)benzohydrazide monohydrate.

Project description:In the title benzohydrazide hydrate, C14H12N2O3·H2O, the dihedral angle between the aromatic rings is 58.11 (6)° and the C=O and N-H groups adopt an anti orientation. The main twist in the mol-ecule occurs about the C(=O)-Car (ar = aromatic) bond, with an N-C(=O)-Car-Car torsion angle of -43.5 (2)°. In the crystal, the components are linked by N-H⋯O, O-H⋯N and O-H⋯O hydrogen bonds. These inter-actions generate [10-1] chains, with adjacent organic mol-ecules linked by inversion symmetry generating either pairs of N-H⋯O links [R 2 (2)(16) loops] or pairs of O-H⋯O links [R 2 (2)(20) loops]. Pairs of water mol-ecules are located in the R 2 (2)(20) loops and form their own O-H⋯O and O-H⋯N hydrogen bonds to adjacent organic mol-ecules in the chain. Finally, an inter-chain O-H⋯O hydrogen-bond link from the 4-hy-droxy group generates (010) sheets.

| S-EPMC4186143 | biostudies-literature

(Z)-4-(2-Hy-droxy-benzyl-idene)-1-methyl-2-phenyl-1H-imidazol-5(4H)-one.

Project description:In the title compound, C(17)H(14)N(2)O(2), the asymmetric unit comprises two mol-ecules that are comformationally similar [the dihedral angles between the phenyl rings in each are 46.35 (2) and 48.04 (3)°], with the conformation stabilized by intra-molecular O-H⋯N hydrogen bonds, which generate S(7) rings. In the crystal, inversion-related mol-ecules are linked by pairs of weak C-H⋯O hydrogen bonds, forming dimers with an R(2) (2)(16) graph-set motif. Weak inter-ring π-π stacking is observed in the structure, the shortest centroid-to-centroid distance being 3.7480 (13) Å.

| S-EPMC3297947 | biostudies-literature

6-Hy-droxy-5,7,8-trimethyl-chroman-2-one.

Project description:The title compound, C(12)H(14)O(3), consists of a chromanone unit with an -OH substituent at the 4-position and methyl substituents on the remaining C atoms of the aromatic ring. The fused pyran-one ring adopts a distorted envelope conformation with the methyl-ene group adjacent to the carbonyl carbon as the flap atom. The crystal structure is stabilized by classical O-H?O hydrogen bonds and weak C-H?O and C-H?? inter-actions, generating a three-dimensional network.

| S-EPMC3151777 | biostudies-literature

(2E)-N'-[(E)-2-Hy-droxy-benzyl-idene]-3-phenyl-prop-2-enohydrazide.

Project description:In the non-planar title compound, C(16)H(14)N(2)O(2), the dihedral angle between the phenyl rings is 16.67?(8)°. An E conformation is found for each of the imine [1.286?(2)?Å] and ethyl-ene [1.335?(2)?Å] bonds. The amide O and H atoms are anti, and an intra-molecular hy-droxy O-H?N hydrogen bond is noted. The formation of N-H?O(hy-droxy) hydrogen bonds in the crystal packing leads to helical chains along the b axis. Supra-molecular layers in the ab plane are formed as the chains are linked by C-H?O inter-actions.

| S-EPMC3394040 | biostudies-literature

(3E,5E)-3,5-Bis(4-hy-droxy-benzyl-idene)oxan-4-one.

Project description:In the title compound, C(19)H(16)O(4), there are two 4-hy-droxy-benzyl substituents on the oxan-4-one (tetra-hydro-pyran-4-one) ring, which exhibits an envelope conformation. The dihedral angles between pyran-one ring and the two benzene rings are 26.69?(9) and 36.01?(9)° while the benzene rings make a dihedral angle of 20.88?(10)°. In the crystal, mol-ecules are linked by inter-molecular O-H?O hydrogen bonds into a supra-molecular three-dimensional twofold inter-penetrating hydrogen-bonded network.

| S-EPMC3050132 | biostudies-literature

3-(3,4-Dichloro-benzyl-idene)chroman-4-one.

Project description:The distinctive feature of the structure of the title compound, C(16)H(10)Cl(2)O(2), is the formation of a zigzag chain along [100] via Cl?Cl inter-actions [3.591?(1) and 3.631?(1)?Å]. The chroman-one moiety is fused with the benzene ring and adopts a half-chair conformation. The dihedral angle between the benzene ring of the chromanone moiety and the dichlorobenzene plane is 56.14?(8)°.

| S-EPMC3515170 | biostudies-literature

3-Benzyl-idene-6-methoxy-chroman-4-one.

Project description:In the title compound, C(17)H(14)O(3), the dihedral angle between the phenyl ring and the benzene ring of the chromanone moiety is 67.78 (3)°. The six-membered heterocyclic ring of the chromanone moiety adopts a half-chair conformation. The structure is stabilized by weak inter-molecular C-H⋯O inter-actions that link the mol-ecules into inversion dimers.

| S-EPMC2959532 | biostudies-literature

2-Hy-droxy-N'-(4-hy-droxy-benzyl-idene)-3-methyl-benzohydrazide.

Project description:The title compound, C(15)H(14)N(2)O(3), was prepared by condensing 4-hy-droxy-benzaldehyde and 2-hy-droxy-3-methyl-benzo-hydra-zide in methanol. The two benzene rings make a dihedral angle of 19.03 (11)°. An intra-molecular O-H⋯O hydrogen bond is observed. The crystal structure is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds and C-H⋯O inter-actions, which lead to the formation of a three-dimensional network.

| S-EPMC3274990 | biostudies-literature

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