Crystal structures and supra­molecular features of 9,9-dimethyl-3,7-di­aza­bicyclo­[3.3.1]nonane-2,4,6,8-tetra­one, 3,7-di­aza­spiro­[bi­cyclo­[3.3.1]nonane-9,1′-cyclo­penta­ne]-2,4,6,8-tetra­one and 9-methyl-9-phenyl-3,7-di­aza­bicyclo­[3.3.1]nonane-2,4,6,8-tetra­one di­methyl­formamide monosolvate

Acta Crystallographica Section E: Crystallographic Communications

Manaenkova, M.A.¹  Vasilev, E.V.¹  Vatsadze, S.Z.¹  Khrustalev, V.N.²  Venskovsky, N.U.² 

[1] Department of Chemistry, Moscow State University, 1 Leninskie Gory, Moscow 119991, Russian Federation;Inorganic Chemistry Department, Faculty of Science, Peoples' Friendship University of Russia (RUDN University), 6 Miklukho-Maklay St., Moscow 117198, Russian Federation

关键词: CRYSTAL STRUCTURE;    ALCALOIDES;    DIAZABICYCLO[3.3.1]NONANES;    TETRAONES;    SUPRAMOLECULAR CHEMISTRY;    HYDROGEN-BONDING INTERACTIONS;    CRYSTAL STRUCTURE;   

DOI  :  10.1107/S2056989017009458

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

Compounds (I), C9H10N2O4, (II), C11H12N2O4, and (III), C14H12N2O4·C3H7NO represent 9,9-disubstituted-3,7-di­aza­bicyclo­[3.3.1]nonane-2,4,6,8-tetra­one deriv­atives with very similar mol­ecular geometries for the bicyclic framework: the dihedral angle between the planes of the imide groups is 74.87 (6), 73.86 (3) and 74.83 (6)° in (I)–(III), respectively. The dimethyl derivative (I) is positioned on a crystallographic twofold axis and its overall geometry deviates only slightly from idealized C2v symmetry. The spiro-cyclo­pentane derivative (II) and the phen­yl/methyl analog (III) retain only inter­nal Cs symmetry, which in the case of (II) coincides with crystallographic mirror symmetry. The cyclo­pentane moiety in (II) adopts an envelope conformation, with the spiro C atom deviating from the mean plane of the rest of the ring by 0.548 (2) Å. In compound (III), an N—H⋯O hydrogen bond is formed with the di­methyl­formamide solvent mol­ecule. In the crystal, both (I) and (II) form similar zigzag hydrogen-bonded ribbons through double inter­molecular N—H⋯O hydrogen bonds. However, whereas in (I) the ribbons are formed by two trans-arranged O=C—N—H amide fragments, the amide fragments are cis-positioned in (II). The formation of ribbons in (III) is apparently disrupted by participation of one of its N—H groups in hydrogen bonding with the solvent mol­ecule. As a result, the mol­ecules of (III) form zigzag chains rather than the ribbons through inter­molecular N—H⋯O hydrogen bonds. The crystal of (I) was a pseudo-merohedral twin.

【 授权许可】

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