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Crystal structure of 2-bromo-benzoic acid at 120?K: a redetermination.

ABSTRACT: The crystal structure of the title compound, C7H5BrO2, was originally studied using photographic data at room temperature with Cu K? radiation [Ferguson & Sim (1962 ?). Acta Cryst. 15, 346-350]. The present study was undertaken at 120?K with a CCD diffractometer using Cu K? radiation, and resulted in improved geometrical parameters. In the mol-ecule, the carb-oxy group is inclined to the benzene ring by 18.7?(2)° and there is a close intra-molecular Br?O contact of 3.009?(3)?Å. In the crystal, mol-ecules are linked by pairs of O-H?O hydrogen bonds, forming inversion dimers with the classical R 2 (2)(8) ring motif for carb-oxy-lic acids. Neighbouring dimers are linked by weak C-H?O hydrogen bonds, forming tapes propagating in [1-10]. Adjacent tapes inter-act by slipped parallel ?-? inter-actions [inter-centroid distance = 3.991?(2), inter-planar distance = 3.509?(2)?Å, slippage = 1.900?Å] to form columns approximately along the b-axis direction. Neighbouring columns inter-act dispersively, forming a three-dimensional framework structure.

SUBMITTER: Kowalska K

PROVIDER: S-EPMC4257184 | biostudies-literature | 2014 Oct

REPOSITORIES: biostudies-literature

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Crystal structure of 2-bromo-benzoic acid at 120 K: a redetermination.

Kowalska Kornelia K Trzybiński Damian D Sikorski Artur A

Acta crystallographica. Section E, Structure reports online 20140930 Pt 10

The crystal structure of the title compound, C7H5BrO2, was originally studied using photographic data at room temperature with Cu Kα radiation [Ferguson & Sim (1962 ▶). Acta Cryst. 15, 346-350]. The present study was undertaken at 120 K with a CCD diffractometer using Cu Kα radiation, and resulted in improved geometrical parameters. In the mol-ecule, the carb-oxy group is inclined to the benzene ring by 18.7 (2)° and there is a close intra-molecular Br⋯O contact of 3.009 (3) Å. In the crystal, m ...[more]

PMID: 25484717

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Project description:The structure of zymonic acid (systematic name: 4-hy-droxy-2-methyl-5-oxo-2,5-di-hydro-furan-2-carb-oxy-lic acid), C6H6O5, which had previously eluded crystallographic determination, is presented here for the first time. It forms by intra-molecular condensation of parapyruvic acid, which is the product of aldol condensation of pyruvic acid. A redetermination of the crystal structure of pyruvic acid (systematic name: 2-oxo-propanoic acid), C3H4O3, at low temperature (90 K) and with increased precision, is also presented [for the previous structure, see: Harata et al. (1977 ▸). Acta Cryst. B33, 210-212]. In zymonic acid, the hy-droxy-lactone ring is close to planar (r.m.s. deviation = 0.0108 Å) and the dihedral angle between the ring and the plane formed by the bonds of the methyl and carb-oxy-lic acid carbon atoms to the ring is 88.68 (7)°. The torsion angle of the carb-oxy-lic acid group relative to the ring is 12.04 (16)°. The pyruvic acid mol-ecule is almost planar, having a dihedral angle between the carb-oxy-lic acid and methyl-ketone groups of 3.95 (6)°. Inter-molecular inter-actions in both crystal structures are dominated by hydrogen bonding. The common R 2 2(8) hydrogen-bonding motif links carb-oxy-lic acid groups on adjacent mol-ecules in both structures. In zymonic acid, this results in dimers about a crystallographic twofold of space group C2/c, which forces the carb-oxy-lic acid group to be disordered exactly 50:50, which scrambles the carbonyl and hydroxyl groups and gives an apparent equalization of the C-O bond lengths [1.2568 (16) and 1.2602 (16) Å]. The other hydrogen bonds in zymonic acid (O-H⋯O and weak C-H⋯O), link mol-ecules across a 21-screw axis, and generate an R 2 2(9) motif. These hydrogen-bonding inter-actions propagate to form extended pleated sheets in the ab plane. Stacking of these zigzag sheets along c involves only van der Waals contacts. In pyruvic acid, inversion-related mol-ecules are linked into R 2 2(8) dimers, with van der Waals inter-actions between dimers as the only other inter-molecular contacts.

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Crystal structure of 2-bromo-benzoic acid at 120?K: a redetermination.

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Crystal structure of 2-bromo-benzoic acid at 120 K: a redetermination.

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