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2-(2-甲基苯甲酰基)苯甲酸:一种γ-酮酸中的双分子氢键

2-(2-Methyl-benzo-yl)benzoic acid: catemeric hydrogen bonding in a γ-keto acid.

作者信息

Platosz Natalia A, Lalancette Roger A, Thompson Hugh W, Newman Jacob M, Schachter Ari

机构信息

Carl A. Olson Memorial Laboratories, Department of Chemistry, Rutgers University, Newark, NJ 07102 , USA.

出版信息

Acta Crystallogr Sect E Struct Rep Online. 2013 Sep 18;69(Pt 10):o1547-8. doi: 10.1107/S1600536813025099. eCollection 2013.

Abstract

The crystal structure of the title compound, C15H12O3, displays catemeric aggregation involving O-H⋯O hydrogen bonds progressing from the carboxyl group of one mol-ecule to the ketone O atom of another glide-related neighbor. The mol-ecule is twisted, with the toluene 80.61 (3)° out of plane with respect to the phenyl group of the benzoic acid. The acid group makes a dihedral angle of 13.79 (14)° with the attached phenyl ring. The mol-ecules are achiral, but the space group glide planes create alternating conformational chirality in the chain units. The four hydrogen-bonding chains progress along [001] in an A-A-B-B pattern (right-to-left versus left-to-right), and are related to each other by the center of symmetry at (0.5, 0.5, 0.5) in the chosen cell. There is one close contact (2.54 Å) between a phenyl H atom and the acid carbonyl from a symmetry-related mol-ecule.

摘要

标题化合物C₁₅H₁₂O₃的晶体结构呈现出二聚体聚集,涉及从一个分子的羧基到另一个滑移相关相邻分子的酮O原子的O—H⋯O氢键。该分子呈扭曲状,甲苯相对于苯甲酸的苯基平面外倾80.61 (3)°。酸基团与相连的苯环形成13.79 (14)°的二面角。分子是非手性的,但空间群滑移面在链单元中产生交替的构象手性。四条氢键链沿[001]以A - A - B - B模式(从右到左与从左到右)延伸,并通过所选晶胞中(0.5, 0.5, 0.5)处的对称中心相互关联。一个苯基H原子与一个对称相关分子的酸羰基之间存在一个近距离接触(2.54 Å)。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/56d4/3790413/72ede798bf6e/e-69-o1547-fig1.jpg

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