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2,6-Bis(trifluoro-meth-yl)benzoic acid.

ABSTRACT: 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.

SUBMITTER: Tobin JM

PROVIDER: S-EPMC2969748 | biostudies-literature | 2009 May

REPOSITORIES: biostudies-literature

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2,6-Bis(trifluoro-meth-yl)benzoic acid.

Tobin John M JM Masuda Jason D JD

Acta crystallographica. Section E, Structure reports online 20090507 Pt 6

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. ...[more]

PMID: 21583086

Similar Datasets

A new polymorph of 2,6-bis-(trifluoro-meth-yl)benzoic acid.

Project description:The asymmetric unit of a second polymorph of the title compound, C(9)H(4)F(6)O(2), contains five independent mol-ecules, which form hydrogen-bonded O-H?O dimers about inversion centers. The most significant structural difference between this structure and that of the first polymorph [Tobin & Masuda (2009 ?). Acta Cryst. E65, o1217] is the hydrogen-bonded, dimeric orientation of the carb-oxy-lic acid functionalities.

| S-EPMC3089103 | biostudies-other

2-Methyl-sulfonyl-4-(trifluoro-meth-yl)benzoic acid.

Project description:In the title mol-ecule, C(9)H(7)F(3)O(4)S, the S and the methyl C atoms of the methyl-sulfonyl group deviate from the benzene ring plane by 0.185?(2) and -1.394?(3)?Å, respectively. In the crystal, O-H?O hydrogen bonds link the mol-ecules into chains along [201]. Weak C-H?O inter-actions further link these chains into layers parallel to the ac plane.

| S-EPMC3379423 | biostudies-literature

N,N'-Bis[4-(trifluoro-meth-yl)phen-yl]pyridine-2,6-dicarboxamide.

Project description:In the title mol-ecule, C(21)H(13)F(6)N(3)O(2), the pyridine ring forms dihedral angles of 1.7?(1) and 5.2?(1)° with the two benzene rings. In the crystal structure, inter-molecular N-H?O hydrogen bonds and ??? inter-actions [centroid-centroid distance of 3.628?(3)?Å between aromatic rings] link mol-ecules into stacks along the c axis. The two trifluoro-methyl groups are each rotationally disordered between two orientations, with occupancy ratios of 0.58?(1):0.42?(1) and 0.55?(1):0.45?(1).

| S-EPMC2979671 | biostudies-literature

2-(Trifluoro-meth-yl)benzoic acid.

Project description:In the title compound, C(8)H(5)F(3)O(2), a halogenated derivative of benzoic acid, the carboxyl group is tilted by 16.8?(3)° with respect to the plane of the aromatic ring. In the crystal, O-H?O hydrogen bonding gives rise to carb-oxy-lic acid dimers, which are further connected into double chains along [1,1/4,1] by C-H?O contacts. C-H?F and C-F?? contacts are also observed.

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3-[2-Chloro-4-(trifluoro-meth-yl)phen-oxy]benzoic acid.

Project description:The asymmetric unit of the title compound, C(14)H(8)ClF(3)O(3), comprises two independent mol-ecules. The rings in each molecule are connected together via O-H?O hydrogen bonds to form classical hydrogen-bonded carb-oxy-lic acid dimers. The dihedral angles between the benzene rings are 80.7?(1) and 68.7?(1)°.

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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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Diethyl 2,6-dihy-droxy-4-(3-nitro-phen-yl)-2,6-bis-(trifluoro-meth-yl)piperidine-3,5-dicarboxyl-ate.

Project description:In the title compound, C(19)H(20)F(6)N(2)O(8), the eth-oxy and ethyl groups are disordered over two sets of sites, with occupancy ratios of 0.212?(18):0.788?(18) and 0.746?(6):0.254?(6), respectively. The piperidine ring adopts a chair conformation. In the mol-ecule, intra-molecular O-H?O hydrogen bonds form two S(6) ring motifs. In the crystal, mol-ecules are linked via O-H?O and C-H?O hydrogen bonds, forming dimers.

| S-EPMC3275076 | biostudies-literature

3,5-Bis[(pyridin-4-yl)meth-oxy]benzoic acid.

Project description:Single crystals of the title compound, C19H16N2O4, were obtained under hydro-thermal conditions by an unintended recrystallization of the employed microcrystalline starting material. The [(pyridin-4-yl)meth-oxy]benzoic acid unit is nearly planar, with a maximum deviation from the least-squares plane of 0.194?(2)?Å. This plane is inclined by 35.82?(6)° to that defined by the second (pyridin-4-yl)meth-oxy group [in which the largest deviation from the least-squares plane is 0.013?(2)?Å]. In the crystal, mol-ecules are linked by O-H?N hydrogen bonds involving the acid hy-droxy group and a pyridine N atom into chains parallel to [-201].

| S-EPMC3588300 | biostudies-literature

The co-crystal N,N'-bis-[(pyridin-1-ium-2-yl)meth-yl]ethane-dithio-amide bis-(2,6-di-nitro-benzoate)-2,6-di-nitro-benzoic acid (1/4).

Project description:The asymmetric unit of title co-crystal, C14H16N4S2 (2+)·2C7H3N2O6 (-)·4C7H4N2O6, comprises a centrosymmetric dipyridinium dication, a 2,6-di-nitro-benzoate anion and two independent 2,6-di-nitro-benzoic acid mol-ecules. The pyridin-ium rings are each approximately perpendicular to the central di-thio-amide unit [dihedral angle = 80.67?(12)°]. The carboxyl-ate/carb-oxy-lic acid groups are approximately perpendicular to the benzene ring to which they are attached [dihedral angles = 78.85?(16), 81.46?(19) and 71.28?(15)°]. By contrast, the major twist exhibited by a nitro group is manifested in a dihedral angle of 32.66?(17)°. The most prominent feature of the crystal packing is linear supra-molecular chains along [1-10], featuring O-H?O(carboxyl-ate) and pyridinium-N-H?O hydrogen bonds. These are consolidated into a three-dimensional architecture by thio-amide-nitro N-H?O, C-H?O and ?-? [inter-centroid distance = 3.524?(2)?Å] inter-actions. One of the nitro O atoms was refined over two sites; the major site was 0.65?(7) occupied.

| S-EPMC3790379 | biostudies-literature

1,2-Bis{bis-[4-(trifluoro-meth-yl)phen-yl]phosphino}ethane.

Project description:Crystals of the title compound, C(30)H(20)F(12)P(2) or R(2)PCH(2)CH(2)PR(2) (R = 4-C(6)H(4)CF(3)), were inadvertently prepared while attempting to recrystallize a crude sample of trans-Re(Cl)(N(2))(R(2)PCH(2)CH(2)PR(2))(2) from diethyl ether. The molecule lies on a center of inversion. One of the rings lies approximately in the P-C-C-P plane; the dihedral angle is 174.53°.The other ring is not quite perpendicular; the dihedral angle is 71.1°. The compound is isostructural with the R = Ph, 4-C(6)H(4)CH(3) and 4-C(6)H(4)CH(2)CH(3) analogues. It is well known that the basicity of phosphines and diphosphines can be altered by changing the electron-donating ability of R; however, the structural parameters for the title compound do not significantly differ from those of the aforementioned substituted-phenyl compounds.

| S-EPMC2960220 | biostudies-literature

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