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Redetermination of 2,6-dimethoxy-benzoic acid.

ABSTRACT: The crystal structure of the title compound, C(9)H(10)O(4), was first reported by Swaminathan, Vimala & Lotter [Acta Cryst. (1976), B32, 1897-1900]. It has been re-examined, improving the precision of the derived geometric parameters. The asymmetric unit comprises a non-planar independent mol-ecule, as the meth-oxy substituents force the carb-oxy group to be twisted away from the plane of the aromatic ring by 56.12?(9)°. Due to the anti-planar conformation adopted by the OH group, the mol-ecular components do not form the conventional dimeric units, but are associated in the crystal in chains stabilized by linear O-H?O hydrogen bonds, involving the OH groups and the carbonyl O atoms, which form C(3) motifs.

SUBMITTER: Portalone G

PROVIDER: S-EPMC2968263 | biostudies-other | 2009

REPOSITORIES: biostudies-other

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Redetermination of 2,6-dimethoxy-benzoic acid.

Portalone Gustavo G

Acta crystallographica. Section E, Structure reports online 20090117 Pt 2

The crystal structure of the title compound, C(9)H(10)O(4), was first reported by Swaminathan, Vimala & Lotter [Acta Cryst. (1976), B32, 1897-1900]. It has been re-examined, improving the precision of the derived geometric parameters. The asymmetric unit comprises a non-planar independent mol-ecule, as the meth-oxy substituents force the carb-oxy group to be twisted away from the plane of the aromatic ring by 56.12 (9)°. Due to the anti-planar conformation adopted by the OH group, the mol-ecular ...[more]

PMID: 21581932

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Redetermination of 3-methyl-benzoic acid.

Project description:The asymmetric unit of the title compound, C(8)H(8)O(2), contains two crystallographically independent mol-ecules, which form dimers linked by O⋯H-O hydrogen bonds. The benzene rings in the dimers are inclined at a dihedral angle of 7.30 (8)° and both methyl groups display rotational disorder. This redetermination results in a crystal structure with significantly higher precision than the original determination [Ellas & García-Blanco (1963 ▶). Acta Cryst. 16, 434], in which the authors reported only the unit-cell parameters and space group, without any detailed information on the atomic arrangement. In the crystal, dimers are connected by weak C-H⋯O inter-actions, forming R(2) (2)(10) and R(4) (4)(18) rings along [110] and an infinite zigzag chain of dimers along the [001] direction also occurs.

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2,6-Difluoro-benzoic acid.

Project description:In the title compound, C(7)H(4)F(2)O(2), the dihedral angle between the benzene ring and the carboxyl-ate group is 33.70?(14)°. In the crystal structure, inversion dimers linked by pairs of O-H?O hydro-gren bonds occur, generating R(2) (2)(8) loops. The dimers are linked into sheets lying parallel to (102) by C-H?F hydrogen bonds.

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A redetermination of 2-nitro-benzoic acid.

Project description:The crystal structure of the title compound, C(7)H(5)NO(4), was first reported by Kurahashi, Fukuyo & Shimada [(1967). Bull. Chem. Soc. Jpn, 40, 1296]. It has been re-examined, improving the precision of the derived geometric parameters. The asymmetric unit comprises a non-planar independent mol-ecule, as the nitro and the carb-oxy substituents force each other to be twisted away from the plane of the aromatic ring by 54.9 (2) and 24.0 (2)°, respectively. The mol-ecules form a conventional dimeric unit via centrosymmetric inter-molecular hydrogen bonds.

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Project description:The title compound, C(9)H(4)F(6)O(2), contains two mol-ecules in the asymmetric unit, one of which exhibits disorder in both of its trifluoro-methyl groups. The dihedral angles between the benzene ring and the carboxyl group are 71.5 (2) and 99.3 (2)° in the two independent mol-ecules. The compound exhibits a catemeric structure resulting from inter-molecular O-H⋯O hydrogen bonding between the carboxyl groups.

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Project description:The benzoic acid mol-ecule of the title compound, C4H5ClN4·C7H6O2, is approximately planar, with a dihedral angle of 1.28?(9)° between the carb-oxy group and the benzene ring. In the crystal, two acid and two base mol-ecules are linked through N-H?O and O-H?N hydrogen bonds, forming a centrosymmetric 2 + 2 unit with R2(2)(8) and R4(2)(8) motifs. These units are further linked through a pair of N-H?N hydrogen bonds into a tape structure along [1-20]. The crystal structure also features weak ?-? [centroid-centroid distance = 3.5984?(11)?Å] and C-H?? inter-actions.

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2,6-Di-bromo-3,4,5-tri-meth-oxy-benzoic acid.

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A new polymorph of 2,6-dimeth-oxy-benzoic acid.

Project description:A new crystalline form of 2,6-dimeth-oxy-benzoic acid, C(9)H(10)O(4), crystallizing in a tetra-gonal unit cell has been identified during screening for co-crystals. The asymmetric unit comprises a non-planar independent mol-ecule with a synplanar conformation of the carb-oxy group. The sterically bulky o-meth-oxy substituents force the carb-oxy group to be twisted away from the plane of the benzene ring by 65.72 (15)°. The carb-oxy group is disordered over two sites about the C-C bond [as indicated by the almost equal C-O distances of 1.254 (3) and 1.250 (3) Å], the occupancies of the disordered carboxym H atoms being 0.53 (5) and 0.47 (5). In the known ortho-rhom-bic form reported by Swaminathan et al. [Acta Cryst. (1976), B32, 1897-1900], due to the anti-planar conformation adopted by the OH group, the mol-ecular components are associated in the crystal in chains stabilized by linear O-H⋯O hydrogen bonds. However, in the new tetra-gonal polymorph, mol-ecules form dimeric units via pairs of O-H⋯O hydrogen bonds between the carb-oxy groups.

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

Project description: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.

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Redetermination of 1,4-dimethoxy-benzene.

Project description:The structure of the centrosymmetric title compound, C(8)H(10)O(2), originally determined by Goodwin et al. [Acta Cryst.(1950), 3, 279-284], has been redetermined to modern standards of precision to aid in its use as a model compound for (13)C chemical-shift tensor measurements in single-crystal NMR studies. In the crystal structure, a C-H?O inter-action helps to establish the packing.

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2-[2,6-Bis(pyrazin-2-yl)pyridin-4-yl]benzoic acid.

Project description:In the title compound, C20H13N5O2, the two pyrazine rings are nearly coplanar with the central pyridine ring, forming dihedral angles of 2.21?(9) and 4.57?(9)°. In contrast, the strong steric hindrance caused by the ortho-carboxyl group on the phenyl ring makes this ring rotate out of the attached pyridine ring plane by 52.60?(9)°. The carboxyl group is twisted from the phenyl ring by 22.6?(1)°. In the crystal, aromatic ?-? stacking inter-actions [centroid-centroid distances = 3.9186?(4) and 3.9794?(5)?Å] occur between the anti-parallel mol-ecules, generating infinite chains along [100]. O-H?O hydrogen bonds connect the chains, leading to the formation of a two-dimensional supra-molecular network parallel to (010). Inter-molecular C-H?N hydrogen bonds are also observed.

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