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2-(2-溴苄叉基)-5-(4-羟基苯基)-7-甲基-3-氧代-2,3-二氢-5H-1,3-噻唑并[3,2-a]嘧啶-6-羧酸甲酯

Methyl 2-(2-bromo-benzyl-idene)-5-(4-hy-droxy-phen-yl)-7-methyl-3-oxo-2,3-dihydro-5H-1,3-thia-zolo[3,2-a]pyrimidine-6-carboxyl-ate.

作者信息

Nagarajaiah H, Fathima Nikhath, Begum Noor Shahina

机构信息

Department of Studies in Chemistry, Bangalore University, Bangalore 560 001, Karnataka, India.

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2012 Apr 1;68(Pt 4):o1257-8. doi: 10.1107/S1600536812013311. Epub 2012 Mar 31.

Abstract

In the title compound, C(22)H(17)BrN(2)O(4)S, the central dihydropyrimidine ring, with a chiral C atom, is significantly puckered and adopts a half-chair conformation with the chiral C atom displaced from the mean plane of the remaining ring atoms by 0.305 (6) Å. The hydroxy-phenyl ring is positioned axially to the pyrimidine ring and almost bisects it, the dihedral angle between the mean-planes of the two rings being 89.78 (12)°. The meth-oxy-carbonyl group is disordered over two sites with an occupancy ratio of 0.568 (5):0.432 (5), resulting in a major and a minor conformer. In the crystal, O-H⋯N and C-H⋯S inter-actions result in sheets along the c axis. The supra-molecular assembly is stabilized by π-π stacking inter-actions between the 2-bromo-benzyl-idene and thia-zolopyrimidine rings [centroid-centroid distance = 3.632 (1) Å]. In addition, C-H⋯π inter-actions are also observed in the crystal structure.

摘要

在标题化合物C₂₂H₁₇BrN₂O₄S中,具有一个手性碳原子的中心二氢嘧啶环明显呈褶皱状,采取半椅式构象,手性碳原子偏离其余环原子的平均平面0.305 (6) Å。羟基苯环轴向位于嘧啶环上且几乎将其平分,两个环的平均平面之间的二面角为89.78 (12)°。甲氧基羰基在两个位置上无序,占有率比为0.568 (5):0.432 (5),产生一个主要构象体和一个次要构象体。在晶体中,O—H⋯N和C—H⋯S相互作用导致沿c轴形成层状结构。超分子组装通过2-溴亚苄基环和噻唑并嘧啶环之间的π-π堆积相互作用得以稳定[质心-质心距离 = 3.632 (1) Å]。此外,在晶体结构中还观察到C—H⋯π相互作用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/243c/3344184/4dea407533db/e-68-o1257-fig1.jpg

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