Crystal structures of two chiral piperidine derivatives: 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one and 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione

Acta Crystallographica Section E: Crystallographic Communications

Romero, N.³  Terá⁴  Roa, L.F.⁶  Gnecco, D.⁷  s, S.^1,12  Bernè^1,13  n, J.L.^1,16 

[1] Centro de QuíInstituto de FíUniversidad Juámica de Ciencias Bámica, Instituto de Ciencias, Benemén Acadén, Jalpa de Mén, Tabasco, Mexico;ndez AP 24, Cunduacánoma de Puebla, 72570 Puebla, Pue., Mexico;noma de Puebla, Av. San Claudio y 18 Sur, 72570 Puebla, Pue., Mexico;noma de Tabasco, Divisiórez Autórita Universidad Autósica, Benemésicas, Km. 1 carretera Cunduacá

关键词: CRYSTAL STRUCTURE;    PIPERIDINE;    PIPERIDONE;    THIONE;    RING CONFORMATION;   

DOI  :  10.1107/S2056989015017119

学科分类：数学（综合）

来源: International Union of Crystallography

【 摘 要 】

The crystal structures of the two title piperidine derivatives show different conformations for the six-membered heterocycle. The N-substituted 4-piperidinone 1-[(1R)-2-hy­droxy-1-phenyl­eth­yl]piperidin-4-one, C13H17NO2, (I), has a chair conformation, while the piperidine substituted in position 2 with a thio­carbonyl group, 8-[(1S)-1-phenyl­eth­yl]-1,4-dioxa-8-aza­spiro­[4.5]decane-7-thione, C15H19NO2S, (II), features a half-chair conformation. Comparison of the two structures, and data retrieved from the literature, suggests that the conformational flexibility is mainly related to the hybridization state of the C atom α to the piperidinic N atom: a Csp3 atom favours the chair conformer, while a Csp2 atom distorts the ring towards a half-chair conformer. In the crystal structure of (I), weak C—H⋯O hydrogen bonds link the mol­ecules into supra­molecular chains propagating along the b-axis direction. In the crystal of (II), the mol­ecules are linked by weak C—H⋯S contacts into supra­molecular chains propagating along the b-axis direction.

【 授权许可】

CC BY