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3,4,5-Trihydr-oxy-N'-(1H-indol-2-ylmethyl-idene)benzohydrazide-1H-indole-2-carbaldehyde azine-methanol (2/1/2).

ABSTRACT: The title compound, 2C(16)H(13)N(3)O(4)·C(18)H(14)N(4)·2CH(4)O, was crystallized from the reaction between 3,4,5-trihydroxy-benzoyl-hydrazine and indole-2-carbaldehyde in a mixture of ethanol and methanol. The compound is a stoichiometric 2:1 cocrystal of the methanol-solvated reaction product, 3,4,5-trihydr-oxy-N'-(1H-indol-2-ylmethyl-idene)benzohydrazide and 1H-indole-2-carbaldehyde azine that arose unexpectedly during the synthesis. The former mol-ecules are linked by O-H?O hydrogen bonds and also by ?-? stacking inter-actions between benzoyl-hydrazide rings into a two-dimensional network. The methanol solvent mol-ecules are hydrogen bonded to this network. The centrosymmetric azine mol-ecules are not engaged in hydrogen bonding.

SUBMITTER: Khaledi H

PROVIDER: S-EPMC2980105 | BioStudies | 2009-01-01

REPOSITORIES: biostudies

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1H-Indole-3-carbaldehyde azine.

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Project description:In the title compound, C(20)H(18)N(2)O(3), the C=C bond of the acrylonitrile group that links the indole and the 3,4,5-trimeth-oxy-phenyl 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). Mol-ecules are linked into head-to-tail chains that propagate along the b-axis direction by bifurcated N-H?O inter-molecular hydrogen bonds, which form an R(1) (2)(5) motif between the indole NH group and the two meth-oxy O atoms furthest from the nitrile group.

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Project description:(Z)-5-[2-(Benzo[b]thio-phen-2-yl)-1-(3,5-di-meth-oxy-phen-yl)ethen-yl]-1H-tetrazole methanol monosolvate, C19H16N4O2S·CH3OH, (I), was prepared by the reaction of (Z)-3-(benzo[b]thio-phen-2-yl)-2-(3,5-di-meth-oxy-phen-yl)acrylo-nitrile with tri-butyl-tin azide via a [3 + 2]cyclo-addition azide condensation reaction. The structurally related compound (Z)-5-[2-(benzo[b]thio-phen-3-yl)-1-(3,4,5-tri-meth-oxy-phen-yl)ethen-yl]-1H-tetra-zole, C20H18N4O3S, (II), was prepared by the reaction of (Z)-3-(benzo[b]thio-phen-3-yl)-2-(3,4,5-tri-meth-oxy-phen-yl)acrylo-nitrile with tri-butyl-tin azide. Crystals of (I) have two mol-ecules in the asymmetric unit (Z' = 2), whereas crystals of (II) have Z' = 1. The benzo-thio-phene 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 tetra-zole rings of (I) and (II) make dihedral angles with the mean planes of the benzo-thio-phene rings of 88.81?(13) and 88.92?(13)° in (I), and 60.94?(6)° in (II). The di-meth-oxy-phenyl and tri-meth-oxy-phenyl rings make dihedral angles with the benzo-thio-phene rings of 23.91?(8) and 24.99?(8)° in (I) and 84.47?(3)° in (II). In both structures, mol-ecules are linked into hydrogen-bonded chains. In (I), these chains involve both tetra-zole and methanol, and are parallel to the b axis. In (II), mol-ecules are linked into chains parallel to the a axis by N-H?N hydrogen bonds between adjacent tetra-zole rings.

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2-Hy-droxy-5-[(E)-(1H-indol-3-yl-methyl-idene)aza-nium-yl]benzoate.

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2010-01-01 | S-EPMC3011759 | BioStudies

1H-Indole-3-carbaldehyde thio-semi-carbazone.

Project description:The mol-ecules of the title compound, C(10)H(10)N(4)S, are linked by N-H(indole)?S hydrogen bonds to form a linear hydrogen-bonded chain. There are two independent mol-ecules in the asymmetric unit.

1000-01-01 | S-EPMC2961326 | BioStudies

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