(Z)-3-(1-Benzofuran-2-yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylonitrile

In the title compound, C20H17NO4, the double bond of the acrylonitrile group separating the 1-benzofuran moiety from the 3,4,5-trimeth­oxy­phenyl ring has Z geometry. The 1-benzofuran groups are π–π stacked with inversion-related counterparts such that the furan ring centroid–centroid distance is 3.804 (5) Å. The dihedral angle between the planes of the trimeth­oxy­phenyl ring and the acrylonitrile group is 24.2 (2)°

Crystal structure of ( E

The title compound, C33H35NO6 [systematic name: (Z)-3-(4-{(E)-[(E)-1a,5-dimethyl-9-oxo-2,3,7,7a-tetrahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-8(1aH,6H,9H,10aH,10bH)-ylidene]methyl}phenyl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile methanol hemisolvate], C33H35NO6·0.5CH3OH, was prepared by the reaction of (Z)-3-(4-iodophenyl)-2-(3,4,5-trimethoxyphenyl)acrylonitrile with parthenolide [systematic name: (E)-1a,5-dimethyl-8-methylene-2,3,6,7,7a,8,10a,10b-octahydrooxireno[2′,3′:9,10]cyclodeca[1,2-b]furan-9(1aH)-one] under Heck reaction conditions. The molecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings with a {4-[(Z)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}methylidene group as a substituent. The 4-[(Z)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl group on the parthenolide exocyclic double bond is oriented in a trans position to the lactone ring to form the E isomer. The dihedral angle between the benzene ring of the phenyl moiety and the lactone ring mean plane is 21.93 (4)°

(Z)-3-(1H-Indol-3-yl)-2-(3,4,5-tri­methoxy­phen­yl)acrylonitrile

In the title compound, C20H18N2O3, the C=C bond of the acrylonitrile group that links the indole and the 3,4,5-trimeth­oxy­phenyl rings has Z geometry, with dihedral angles between the plane of the acrylonitrile unit and the planes of the benzene and indole ring systems of 21.96 (5) and 38.94 (7)°, respectively. The acrylonitrile group is planar (r.m.s. deviation from planarity = 0.037 Å). Mol­ecules are linked into head-to-tail chains that propagate along the b-axis direction by bifurcated N—H⋯O inter­molecular hydrogen bonds, which form an R 1 2(5) motif between the indole NH group and the two meth­oxy O atoms furthest from the nitrile group

Crystal Structure of (\u3cem\u3eE\u3c/em\u3e)-13-(pyrimidin-5-yl)parthenolide

The title compound, C19H22N2O3, {systematic name (1aR,4E,7aS,8E,10aS,10bR)-1a,5-dimethyl-8-[(pyrimidin-5-yl)­methylid­ene]-2,3,6,7,7a,8,10a,10b-octa­hydro­oxireno[2′,3′:9,10]cyclo­deca­[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-methyl­ene-2,3,6,7,7a,8,10a,10b-octa­hydro­oxireno[2′,3′:9,10]cyclodeca­[1,2-b]furan-9(1aH)-one] with 5-bromo­pyrimidine under Heck reaction conditions, and was identified as an E isomer. The mol­ecule 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)°

3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-3-hydr­oxy-1-phenyl­indolin-2-one ethanol solvate

In the title compound, C18H16N4O3·C2H5OH, mol­ecules are linked into chains by a series of inter­molecular N—H⋯O, N—H⋯N and O—H⋯O hydrogen bonds which stabilize the crystal structure. The indole and creatinine units make a dihedral angle of 56.45 (4)°. The title compound has two chiral centres. The crystal structure indicates the compound is racemic (RR and SS)

(Z)-Methyl 4-({3-[(2,5-dioxoimidazolidin-4-yl­idene)meth­yl]-1H-indol-1-yl}meth­yl)benzoate

In the title compound, C21H17N3O4, pairs of mol­ecules form a planar[maximum deviation 0.0566 (9) Å] centrosymmetric imidazole dimer via two N—H⋯O hydrogen bonds. These dimeric units are linked by further N—H⋯O hydrogen bonds between the ester carbonyl group and the imidazolidine ring, formiing chains parallel to the c-axis direction. In addition, there are π–π stacking inter­actions between the planar imidazole pairs, with an inter­planar spacing of 3.301 (2) Å. There is a double bond with Z geometry connecting the imidazolidine and indole units

3-(2-Amino-1-methyl-4-oxo-4,5-dihydro-1H-imidazol-5-yl)-5-fluoro-3-hydr­oxy-1-methyl­indolin-2-one methanol hemisolvate

In the title compound, C13H13FN4O3·0.5CH3OH, mol­ecules are packed in the crystal structure by a series of O—H⋯N, N—H⋯O, N—H⋯F and O—H⋯O inter­molecular hydrogen bonds. The indole and creatinine units make a dihedral angle of 60.80 (4)°

Comparison Crystal Structure Conformations of Two Structurally Related Biphenyl Analogues: 4,4\u27-bis[3-(pyrrolidin-1-yl)prop-1-yn-1-yl]-1,1\u27-biphenyl and 4,4\u27-bis{3-[(\u3cem\u3eS\u3c/em\u3e)-2-methylpyrrolidin-1-yl]prop-1-yn-1-yl}-1,1\u27-biphenyl

The title compounds, C26H28N2, (I), and C28H32N2, (II), were designed based on the structure of the potent 910 nicotinic acetyl­choline receptor antagonist ZZ161C {1,1\u27-[[1,1\u27-biphen­yl]-4,4\u27-diylbis(prop-2-yne-3,1-di­yl)]bis­(3,4-di­methyl­pyridin-1-ium) bromide}. In order to improve the druglikeness properties of ZZ161C for potential oral administration, the title compounds (I) and (II) were prepared by coupling 4,4\u27-bis­(3-bromo­prop-1-yn-1-yl)-1,1\u27-biphenyl with pyrrol­idine, (I), and (S)-2-methyl­pyrrolidine, (II), respectively, in aceto­nitrile at room temperature. The asymmetric unit of (I) contains two half mol­ecules that each sit on sites of crystallographic inversion. As a result, the biphenyl ring systems in compound (I) are coplanar. The biphenyl ring system in compound (II), however, has a dihedral angle of 28.76 (11)°. In (I), the two independent mol­ecules differ in the orientation of the pyrrolidine ring (the nitro­gen lone pair points towards the biphenyl rings in one mol­ecule, but away from the rings in the other). The torsion angles about the ethynyl groups between the planes of the phenyl rings and the pyrrolidine ring N atoms are 84.15 (10) and -152.89 (10)°. In compound (II), the corresponding torsion angles are 122.0 (3) and 167.0 (3)°, with the nitro­gen lone pairs at both ends of the mol­ecule directed away from the central biphenyl rings

Crystal Structures of (\u3cem\u3eZ\u3c/em\u3e)-5-[2-(benzo[\u3cem\u3eb\u3c/em\u3e]thiophen-2-yl)-1-(3,5-dimethoxyphenyl)ethenyl]-1\u3cem\u3eH\u3c/em\u3e-tetrazole and (\u3cem\u3eZ\u3c/em\u3e)-5-[2-(benzo[\u3cem\u3eb\u3c/em\u3e]thiophen-3-yl)-1-(3,4,5-trimethoxyphenyl)ethenyl]-1\u3cem\u3eH\u3c/em\u3e-tetrazole

(Z)-5-[2-(Benzo[b]thio­phen-2-yl)-1-(3,5-di­meth­oxy­phen­yl)ethen­yl]-1H-tetrazole methanol monosolvate, C19H16N4O2S·CH3OH, (I), was prepared by the reaction of (Z)-3-(benzo[b]thio­phen-2-yl)-2-(3,5-di­meth­oxy­phen­yl)acrylo­nitrile with tri­butyl­tin azide via a [3 + 2]cyclo­addition azide condensation reaction. The structurally related compound (Z)-5-[2-(benzo[b]thio­phen-3-yl)-1-(3,4,5-tri­meth­oxy­phen­yl)ethen­yl]-1H-tetra­zole, C20H18N4O3S, (II), was prepared by the reaction of (Z)-3-(benzo[b]thio­phen-3-yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylo­nitrile with tri­butyl­tin azide. Crystals of (I) have two mol­ecules in the asymmetric unit (Z′ = 2), whereas crystals of (II) have Z′ = 1. The benzo­thio­phene rings in (I) and (II) are almost planar, with r.m.s deviations from the mean plane of 0.0084 and 0.0037 Å in (I) and 0.0084 Å in (II). The tetra­zole rings of (I) and (II) make dihedral angles with the mean planes of the benzo­thio­phene rings of 88.81 (13) and 88.92 (13)° in (I), and 60.94 (6)° in (II). The di­meth­oxy­phenyl and tri­meth­oxy­phenyl rings make dihedral angles with the benzo­thio­phene rings of 23.91 (8) and 24.99 (8)° in (I) and 84.47 (3)° in (II). In both structures, mol­ecules are linked into hydrogen-bonded chains. In (I), these chains involve both tetra­zole and methanol, and are parallel to the b axis. In (II), mol­ecules are linked into chains parallel to the a axis by N—H⋯N hydrogen bonds between adjacent tetra­zole rings

Crystal Structure of (\u3cem\u3eE\u3c/em\u3e)-13-{4-[(\u3cem\u3eZ\u3c/em\u3e)-2-cyano-2-(3,4,5-trimethoxyphenyl)ethenyl]phenyl}parthenolide methanol hemisolvate

The title compound, C33H35NO6 [systematic name: (Z)-3-(4-{(E)-[(E)-1a,5-dimethyl-9-oxo-2,3,7,7a-tetra­hydro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-8(1aH,6H,9H,10aH,10bH)-yl­idene]meth­yl}phen­yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylo­ni­trile methanol hemisolvate], C33H35NO6·0.5CH3OH, was prepared by the reaction of (Z)-3-(4-iodo­phen­yl)-2-(3,4,5-tri­meth­oxy­phen­yl)acrylo­nitrile with parthenolide [systematic name: (E)-1a,5-dimethyl-8-methyl­ene-2,3,6,7,7a,8,10a,10b-octa­hy­dro­oxireno[2′,3′:9,10]cyclo­deca­[1,2-b]furan-9(1aH)-one] under Heck reaction conditions. The mol­ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings with a {4-[(Z)-2-cyano-2-(3,4,5-tri­meth­oxy­phen­yl)ethen­yl]phen­yl}methyl­idene group as a substituent. The 4-[(Z)-2-cyano-2-(3,4,5-tri­meth­oxy­phen­yl)ethen­yl]phenyl group on the parthenolide exocyclic double bond is oriented in a trans position to the lactone ring to form the E isomer. The dihedral angle between the benzene ring of the phenyl moiety and the lactone ring mean plane is 21.93 (4)°