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Crystal structure of 13-(E)-(2-amino-benzyl-idene)parthenolide.

ABSTRACT: The title compound, C₂₁H₂₅NO₃ [systematic name: (1aR,4E,7aS,8E,10aS,10bR)-8-(2-amino-benzyl-idene)-1a,5-dimethyl-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-9(1aH)-one], was synthesized by the reaction of parthenolide [systematic name (1aR,7aS,10aS,10bS,E)-1a,5-dimethyl-8-methyl-ene-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-9(1aH)-one] with 2-iodo-aniline via Heck reaction conditions. The mol-ecule is composed of fused ten-, five- (lactone), and three-membered (epoxide) rings. The lactone ring shows a flattened envelope-type conformation (r.m.s. deviation from planarity = 0.0477 Å), and bears a 2-amino-benzyl-idene substituent that is disordered over two conformations [occupancy factors 0.901 (4) and 0.099 (4)]. The ten-membered ring has an approximate chair-chair conformation. The dihedral angle between the 2-amino-benzyl-idine moiety (major component) and the lactone ring (mean plane) is 59.93 (7)°. There are no conventional hydrogen bonds, but there are a number of weaker C-H⋯O-type inter-actions.

SUBMITTER: Bommagani S

PROVIDER: S-EPMC6218918 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure of [2-({2-[(2-azanidyl-benzyl-idene)amino]-benzyl-idene}amino)-4-chloro-phenol-ato]nickel(II).

Project description:The title complex, [Ni(C20H14ClN3O)], with an asymmetrically chloride-appended Schiff base ligand has been synthesized and structurally characterized at 100 K. In the compound, the central nickel(II) ion has a square-planar coordination geometry with N3O donors of the π-conjugated tetra-dentate Schiff base ligand. In the crystal, the complexes are connected into an inversion dimer via an Ni⋯Ni inter-action [3.1753 (5) Å] and a pair of π-π inter-actions [centroid-centroid distance = 3.8416 (16) Å]. The dimers are linked via a C-H⋯Cl hydrogen bond, forming a chain along the c-axis direction. The dimer chains inter-act with each other through π-π inter-actions [centroid-centroid distance = 3.8736 (16) Å], forming a layer expanding parallel to the ac plane.

| S-EPMC5382639 | biostudies-literature

Crystal structure of 4-[(E)-(4-nitro-benzyl-idene)amino]-phenol.

Project description:The asymmetric unit of the title compound, C13H10N2O3, contains four independent mol-ecules (I, II, III and IV). Mol-ecule IV shows whole-mol-ecule disorder over two sets of adjacent sites in a 0.669?(10):0.331?(10) ratio. The dihedral angles between the aromatic rings are 32.30?(13)° in mol-ecule I, 2.24?(14)° in II, 41.61?(13)° in III, 5.0?(5)° in IV (major component) and 10.2?(3)° in IV (minor component). In the crystal, mol-ecules are linked into layers lying parallel to (024) by C-H?O and O-H?O inter-actions. The layers inter-act by C-H?? and weak aromatic ?-? stacking inter-actions [centroid-centroid distances = 3.8476?(16), 3.725?(3) and 3.733?(5)?Å].

| S-EPMC4384620 | biostudies-literature

Crystal structure of 3-benzyl-1-[(cyclo-hexyl-idene)amino]-thio-urea.

Project description:The conformation of the title compound, C14H19N3S, is partially determined by an intra-molecular N-H⋯N hydro-gen-bond inter-action, although the N-H⋯N angle of 108° is quite small. The cyclo-hexyl-idene ring has a chair conformation and its mean plane is inclined to the benzene ring by 46.30 (8)°. In the crystal, mol-ecules are linked by pairs of N-H⋯S hydrogen bonds, forming inversion dimers, with an R 2 (2)(8) ring motif. The dimers are reinforced by pairs of C-H⋯S hydrogen bonds, and are linked by further weak C-H⋯S hydrogen bonds, forming chains propagating along [100].

| S-EPMC4719888 | biostudies-literature

Crystal structure of (E)-13-(pyrimidin-5-yl)parthenolide.

Project description:The title compound, C19H22N2O3, {systematic name (1aR,4E,7aS,8E,10aS,10bR)-1a,5-dimethyl-8-[(pyrimidin-5-yl)-methylid-ene]-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-9(1aH)-one} was obtained from the reaction of parthenolide [systematic name (1aR,7aS,10aS,10bR,E)-1a,5-dimethyl-8-methyl-ene-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclodeca-[1,2-b]furan-9(1aH)-one] with 5-bromo-pyrimidine under Heck reaction conditions, and was identified as an E isomer. The mol-ecule possesses ten-, five- (lactone) and three-membered (epoxide) rings with a pyrimidine group as a substituent. The ten-membered ring displays an approximate chair-chair conformation, while the lactone ring shows a flattened envelope-type conformation. The dihedral angle between the pyrimidine moiety and the lactone ring system is 29.43?(7)°.

| S-EPMC4719832 | biostudies-other

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.

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Crystal structure of 1,3-bis-[(<i>E</i>)-benzyl-idene-amino]-propan-2-ol.

Project description:In the title compound, C17H18N2O, the central carbon atom with the OH substituent and one of the (E)-benzyl-idene-amino substituents are disordered over two sets of sites with occupancies of 0.851 (4) and 0.149 (4). The relative positions of the two disorder components is equivalent to a rotation of approximately 60° about the C-N single bond. In the crystal, the mol-ecules are held together by O-H⋯N hydrogen bonds, forming simple C(5) chains along the b-axis direction. In addition, pairs of the chains are further aggregated by weak C-H⋯π inter-actions.

| S-EPMC5382637 | biostudies-literature

(E)-13-(4-Amino-phen-yl)parthenolide.

Project description:The title compound, C21H25NO3 [systematic name: (3aS,9aR,10aR,10bS,E)-3-[(E)-4-(4-amino-benzyl-idene)-6,9a-dimethyl-3a,4,5,8,9,9a,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-2(3H)-one] was obtained from the reaction of parthenolide [synonym: 4,5-ep-oxy-germacra-1(10),11(13)-dieno-12,6-lactone] with 4-iodo-aniline under Heck reaction conditions. It was identified as the E-isomer (conformation about the exocyclic methyl-idene C=C bond; the conformation about the C=C bond in the ten-membered ring is also E). The mol-ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings with a 4-amino-phenyl group as a substituent. The ten-membered ring displays an approximate chair-chair conformation, while the lactone ring has an envelope conformation with the C atom bonded to the ring O atom as the flap. The dihedral angle between the benzene ring of the 4-amino-phenyl moiety and the lactone ring mean plane is 23.50?(8)°. In the crystal, mol-ecules are linked via N-H?O hydrogen bonds, between the amine group and the lactone and epoxide ring O atoms, forming chains propagating along the b-axis direction. Adjacent chains are linked via C-H?O inter-actions, forming an undulating two-dimensional network lying parallel to the plane (001). The absolute structure of the mol-ecule in the crystal was confirmed by resonance scattering [Flack parameter = 0.03?(3)].

| S-EPMC3884358 | biostudies-literature

Crystal structure of 3-benzyl-1-[(1,2,3,4-tetra-hydro-naphthalen-1-yl-idene)amino]-thio-urea.

Project description:In the title compound, C18H19N3S, the dihedral angle between the planes of the benzene rings is 58.63 (8)°. The six-membered ring bonded to the thio-semicarbazide group (r.m.s. deviation = 0.038 Å) adopts a sofa conformation, with one of the methyl-ene-group C atoms as the flap. A short intra-molecular N-H⋯N contact is observed. In the crystal, mol-ecules are linked by weak N-H⋯S inter-actions to generate C(4) chains propagating in the [010] direction, with adjacent mol-ecules related by glide symmetry.

| S-EPMC4719930 | biostudies-literature

Crystal structure of 5-[4-(di-ethyl-amino)-benzyl-idene]-2,2-dimethyl-1,3-dioxane-4,6-dione.

Project description:The title compound, C17H21NO4, consists of substituted Meldrum's acid with a [4-(di-ethyl-amino)-phen-yl]methyl-idene fragment attached to the fifth position. The heterocycle assumes a distorted boat conformation. The planar part of heterocycle is almost coplanar with the benzene ring due to the presence of a long conjugated system in the mol-ecule. This leads to the formation of C-H⋯O-type intra-molecular contacts. As a result of the absence of hydrogen-bond donors in the structure, the crystal packing is controlled by van der Waals forces and weak C-H⋯O inter-actions, which associate the mol-ecules into inversion dimers.

| S-EPMC4647437 | biostudies-literature

Crystal structure of 1,3-bis-[(<i>E</i>)-4-meth-oxy-benzyl-idene-amino]-propan-2-ol.

Project description:The title Schiff base, C19H22N2O3, was synthesized via the condensation reaction of 1,3-di-amino-propan-2-ol with 4-meth-oxy-benzaldehyde using water as solvent. The mol-ecule exists in an E,E conformation with respect to the C=N imine bonds and the dihedral angle between the aromatic rings is 37.25?(15)°. In the crystal, O-H?N hydrogen bonds link the mol-ecules into infinite C(5) chains propagating along the a-axis direction. The packing of these chains is consolidated by C-H?O inter-actions and C-H?? short contacts, forming a three-dimensional network.

| S-EPMC5137596 | biostudies-literature

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