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(1S,3'S,3a'R,6'S)-6'-(2-氯苯基)-3'-[(2R,3S)-1-(4-甲氧基苯基)-4-氧代-3-苯基氮杂环丁烷-2-基]-2-氧代-3',3'a,4',6'-四氢-2H,2'H-螺[苊烯-1,1'-吡咯并[1,2-c][1,3]噻唑]-2',2'-二腈

(1S,3'S,3a'R,6'S)-6'-(2-Chloro-phen-yl)-3'-[(2R,3S)-1-(4-meth-oxy-phen-yl)-4-oxo-3-phenyl-azetidin-2-yl]-2-oxo-3',3'a,4',6'-tetra-hydro-2H,2'H-spiro-[ace-naphthyl-ene-1,1'-pyrrolo-[1,2-c][1,3]thia-zole]-2',2'-dicarbo-nitrile.

作者信息

Devi Seenivasan Karthiga, Srinivasan Thothadri, Rajesh Raju, Raghunathan Raghavachary, Velmurugan Devadasan

机构信息

Centre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India.

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2013 Apr 17;69(Pt 5):o750-1. doi: 10.1107/S1600536813009276. Print 2013 May 1.

Abstract

The mol-ecular conformation of the title compound, C41H29ClN4O3S, is stabilized by intra-molecular C-H⋯O and C-H⋯Cl hydrogen bonds. The thia-zole ring adopts an envelope conformation with the N atom as the flap, while the pyrrolidine ring has a twisted conformation on the N-C bond involving the spiro C atom. The β la-ctam ring makes dihedral angles of 39.74 (15) and 16.21 (16)° with the mean planes of the thia-zole and pyrrolidine rings, respectively. The thia-zole ring mean plane makes dihedral angles of 23.79 (13) and 70.88 (13) ° with the pyrrolidine and cyclo-pentane rings, respectively, while the pyrrolidine ring makes a dihedral angle of 85.63 (13)° with the cyclo-pentane ring. The O atom attached to the β la-ctam ring deviates from its mean plane by 0.040 (2) Å, while the O atom attached to the cyclo-pentane ring deviates from its mean plane by 0.132 (2) Å. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds, forming chains along [010], and C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.6928 (17) Å].

摘要

标题化合物C41H29ClN4O3S的分子构象通过分子内C-H⋯O和C-H⋯Cl氢键得以稳定。噻唑环采取以N原子为翻盖的信封式构象,而吡咯烷环在涉及螺C原子的N-C键上具有扭曲构象。β-内酰胺环与噻唑环和吡咯烷环的平均平面分别形成39.74 (15)°和16.21 (16)°的二面角。噻唑环平均平面与吡咯烷环和环戊烷环的平均平面分别形成23.79 (13)°和70.88 (13)°的二面角,而吡咯烷环与环戊烷环形成85.63 (13)°的二面角。连接到β-内酰胺环的O原子偏离其平均平面0.040 (2) Å,而连接到环戊烷环的O原子偏离其平均平面0.132 (2) Å。在晶体中,分子通过C-H⋯O氢键相连,沿[010]方向形成链状结构,并且存在C-H⋯π和π-π相互作用[质心-质心距离 = 3.6928 (17) Å]。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1a53/3648279/1fa0df640462/e-69-0o750-fig1.jpg

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