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Journal logoIUCrDATA
ISSN: 2414-3146

November 2019 issue

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Cover illustration: The crystal structure of the fumarate salt of the synthetic psychedelic 4-HO-DPT is reported as its tetra­hydrate (systematic name: bis­{[2-(4-hy­droxy-1H-indol-3-yl)eth­yl]bis­(propan-2-yl)aza­nium} but-2-enedioate tetra­hydrate). 4-Hy­droxy-N,N-di-n-propyl­tryptamine, or 4-HO-DPT, is a derivative of psilocin, which is the primary active psychedelic in `magic' mushrooms. Psilocin is the metabolite of psilocybin and its synthetic analogue psilacetin, and is a serotonin-2a agonist which results in its mood-altering effects. Tryptamines, both naturally occurring and their synthetic derivatives have garnered a great deal of inter­est because of their potential to treat depression and post-traumatic stress disorder (PTSD). The solid-state structures of bioactive tryptamine mol­ecules are significant because they define each mol­ecule's physical identity, thereby providing the foundation for all downstream research. For example, such fundamental structural characterization is essential for understanding each mol­ecule's biological and clinical properties via structure-activity relationships. To help further elucidate these properties, the structure of 4-HO-DPT is reported. See: Chadeayne, Pham, Golen & Manke [IUCrData (2019). 4, x191469].

inorganic compounds


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The crystal structure model of RbBrF4 was refined against single-crystal X-ray diffraction data collected at 100 K and compared with the previous results.

metal-organic compounds


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In the title compound, a hydrogen-bonded octa­molybdate anion is coordinated to a protonated bis­(dialk­yl)ammonium ether salt.

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The asymmetric unit of the title compound contains four indium(III) complex anions, four sodium(I) cations and sixteen water mol­ecules. The indium(III) complex anions and sodium(I) cations are alternately connected through coordination bonds between Na+ ions and the carboxyl­ate groups of the complex anions, forming an infinite sixfold left-handed helix along the c-axis direction. In the crystal, the helices are linked by O—H⋯O hydrogen bonds between water mol­ecules bound to Na+ ions and carboxyl­ate groups.

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The title dinuclear complex features a methanol mol­ecule bridging two copper centres.

organic compounds


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The title compound was synthesized via the base-assisted reaction of piperazine and 2-nitro­benyl bromide in toluene

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The title structure crystallizes in a triclinic unit cell as an ion pair with a single disordered solvent mol­ecule. Hydrogen bonding is observed between the carb­oxy­lic acid moiety and the tetra­hydro­furan solvent.

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The title mol­ecule exists in a thio­ketone form, in which weak intra­molecular N—H⋯O and C—H⋯O hydrogen bonds are observed. In the crystal, inter­molecular N—H⋯S and N—H⋯O hydrogen bonds, and π–π inter­actions link the mol­ecules, forming a three-dimensional network.

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The crystal structure of the fumarate salt of the synthetic psychedelic 4-HO-DPT is reported as its tetra­hydrate. A series of N—H⋯O and O—H⋯O hydrogen bonds connect the ions and water mol­ecules of crystallization into a three-dimensional network.

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In the title compound, the dihedral angle between the pyridine and benzene rings is 55.68 (11)°. In the crystal, N—H⋯N hydrogen bonds link the mol­ecules into [010] chains.

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In the title compound, which crystallizes with two mol­ecules in the asymmetric unit, the C≡C distances are almost the same but the Csp3—C≡C angles differ somewhat.

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The title 1,3,4-oxa­diazole derivative is essentially planar, with a dihedral angle of 6.101 (17)° between the phenyl and oxa­diazole rings.

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The title com­pound crystallizes with two independent mol­ecules and one di­chloro­methane solvent mol­ecule in the asymmetric unit. The crystal packing is stabilized by C—H⋯O hydrogen bonds.

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In the title compound, the triazole ring system is inclined at dihedral angles of 4.14 (18) and 69.24 (11)° with the naphthalene ring system and phenyl ring, respectively. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into double columns propagating along the b-axis direction.

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The title compound was prepared by alkynylation of 4-iodo­nitro­benzene, with 1,3-dili­thio­propyne, in the presence of CuI and catalytic amounts of Pd(PPh3)2Cl2.
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