Crystal structures and supra#173;molecular features of 9,9-dimethyl-3,7-di#173;aza#173;bicyclo#173;3.3.1nonane-2,4,6,8-tetra#173;one, 3,7-di#173;aza#173;spiro#173;bi#173;cyclo#173;3.3.1nonane-9,1#8242;-cyclo#173;penta#173;ne-2,4,6,8-tetra#173;one and 9-methyl-9-phenyl-3,7-di#173;aza#173;bicyclo#173;3.3.1nonane-2,4,6,8-tetra#173;one di#173;methyl#173;formamide monosolvate

Vatsadze S.Z.; Manaenkova M.A.; Vasilev E.V.Venskovsky N.U.Khrustalev V.N.

首页> 外文期刊>Acta Crystallographica Section E: Crystallographic Communications >Crystal structures and supra#173;molecular features of 9,9-dimethyl-3,7-di#173;aza#173;bicyclo#173;3.3.1nonane-2,4,6,8-tetra#173;one, 3,7-di#173;aza#173;spiro#173;bi#173;cyclo#173;3.3.1nonane-9,1#8242;-cyclo#173;penta#173;ne-2,4,6,8-tetra#173;one and 9-methyl-9-phenyl-3,7-di#173;aza#173;bicyclo#173;3.3.1nonane-2,4,6,8-tetra#173;one di#173;methyl#173;formamide monosolvate

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Crystal structures and supra#173;molecular features of 9,9-dimethyl-3,7-di#173;aza#173;bicyclo#173;3.3.1nonane-2,4,6,8-tetra#173;one, 3,7-di#173;aza#173;spiro#173;bi#173;cyclo#173;3.3.1nonane-9,1#8242;-cyclo#173;penta#173;ne-2,4,6,8-tetra#173;one and 9-methyl-9-phenyl-3,7-di#173;aza#173;bicyclo#173;3.3.1nonane-2,4,6,8-tetra#173;one di#173;methyl#173;formamide monosolvate

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Compounds (I), C9H10N2O4, (II), C11H12N2O4, and (III), C14H12N2O4#183;C3H7NO represent 9,9-disubstituted-3,7-di#173;aza#173;bicyclo#173;3.3.1nonane-2,4,6,8-tetra#173;one deriv#173;atives with very similar mol#173;ecular geometries for the bicyclic framework: the dihedral angle between the planes of the imide groups is 74.87#8197;(6), 73.86#8197;(3) and 74.83#8197;(6)#176; in (I)#8211;(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-cyclo#173;pentane derivative (II) and the phen#173;yl/methyl analog (III) retain only inter#173;nal Cs symmetry, which in the case of (II) coincides with crystallographic mirror symmetry. The cyclo#173;pentane 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#8197;(2)#8197;#197;. In compound (III), an N#8212;H#8943;O hydrogen bond is formed with the di#173;methyl#173;formamide solvent mol#173;ecule. In the crystal, both (I) and (II) form similar zigzag hydrogen-bonded ribbons through double inter#173;molecular N#8212;H#8943;O hydrogen bonds. However, whereas in (I) the ribbons are formed by two trans-arranged O#61;C#8212;N#8212;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#8212;H groups in hydrogen bonding with the solvent mol#173;ecule. As a result, the mol#173;ecules of (III) form zigzag chains rather than the ribbons through inter#173;molecular N#8212;H#8943;O hydrogen bonds. The crystal of (I) was a pseudo-merohedral twin.

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来源
《Acta Crystallographica Section E: Crystallographic Communications》 |2017年第7期|1097-1101|共5页
作者
Vatsadze S.Z.; Manaenkova M.A.; Vasilev E.V.Venskovsky N.U.Khrustalev V.N.;
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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;

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CRYSTAL STRUCTURE; ALCALOIDES; DIAZABICYCLO3.3.1NONANES; TETRAONES; SUPRAMOLECULAR CHEMISTRY; HYDROGEN-BONDING INTERACTIONS;

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