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4'-Chloro-biphenyl-3-yl 2,2,2-trichloro-ethyl sulfate.

ABSTRACT: The title compound, C(14)H(10)Cl(4)O(4)S, is a 2,2,2-trichloro-ethyl-protected precursor of 4'-chloro-biphenyl-3-yl sulfate, a sulfuric acid ester of 4'-chloro-biphenyl-3-ol. The C(aromatic)-O and O-S bond lengths of the C(aromatic)-O-S unit are comparable to those in structurally analogous biphenyl-4-yl 2,2,2-trichloro-ethyl sulfates with no electro-negative chlorine substituent in the benzene ring with the sulfate ester group. The dihedral angle between the aromatic rings is 27.47 (6)°.

SUBMITTER: Li X

PROVIDER: S-EPMC3008081 | biostudies-literature | 2010 Aug

REPOSITORIES: biostudies-literature

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4'-Chloro-biphenyl-3-yl 2,2,2-trichloro-ethyl sulfate.

Li Xueshu X Parkin Sean S Duffel Michael W MW Robertson Larry W LW Lehmler Hans-Joachim HJ

Acta crystallographica. Section E, Structure reports online 20100818 Pt 9

The title compound, C(14)H(10)Cl(4)O(4)S, is a 2,2,2-trichloro-ethyl-protected precursor of 4'-chloro-biphenyl-3-yl sulfate, a sulfuric acid ester of 4'-chloro-biphenyl-3-ol. The C(aromatic)-O and O-S bond lengths of the C(aromatic)-O-S unit are comparable to those in structurally analogous biphenyl-4-yl 2,2,2-trichloro-ethyl sulfates with no electro-negative chlorine substituent in the benzene ring with the sulfate ester group. The dihedral angle between the aromatic rings is 27.47 (6)°. ...[more]

PMID: 21588655

Similar Datasets

4'-Chloro-biphenyl-4-yl 2,2,2-trichloro-ethyl sulfate.

Project description:The title compound, C(14)H(10)Cl(4)O(4)S, is an inter-mediate in the synthesis of the PCB sulfate monoester of 4'-chloro-biphenyl-4-ol. Both the sulfate monoester and 4'-chloro-biphenyl-4-ol are metabolites of PCB 3 (4-chloro-biphen-yl). There are two mol-ecules with different conformations in the asymmetric unit. The solid state dihedral angles between the benzene rings are 18.52 (10) and 41.84 (16)° in the two mol-ecules, whereas the dihedral angles between the least-squares plane of the sulfated benzene ring and O-S (Ar-C-O-S) are 66.2 (3) and 89.3 (3)°. The crystal was an inversion twin with a refined component fraction of 0.44 (7).

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Project description:The mol-ecular structure of the title compound, C(14)H(11)Cl(3)O(4)S, displays a biphenyl dihedral angle of 4.9 (2)° between the benzene rings, which is significantly smaller than the calculated dihedral angle of 41.2° of biphenyl derivatives without ortho substituents. The C(Ar)-O bond length of 1.432 (4) Å is comparable with other sulfuric acid biphenyl-4-yl ester 2,2,2-trichloro-ether ester derivatives without electronegative substituents in the sulfated phenyl ring.

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3',4'-Dichloro-biphenyl-4-yl 2,2,2-trichloro-ethyl sulfate.

Project description:The four independent mol-ecules in the asymmetric unit of the title compound, C(14)H(9)Cl(5)O(4)S, are related by pseudo-inversion centres. The mol-ecules have C(aromatic)-O bond lengths ranging from 1.426 (10) to 1.449 (9) Å and biphenyl-4-yl sulfate ester bond lengths ranging from 1.563 (6) to 1.586 (6) Å, which is comparable to structurally related sulfuric acid diesters. The dihedral angles between the benzene rings range from 22.5 (4) to 29.1 (4)° and are significantly smaller than the calculated dihedral angle of 41.2°.

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[N-(1-Aza-nidyl-2,2,2-trichloro-ethyl-idene)-2,2,2-trichloro-ethanimidamide]-copper(II).

Project description:The title compound, [Cu(C(4)H(2)Cl(6)N(3))(2)], was obtained by the reaction of CCl(3)CN with ammonia in presence of CuCl. The Cu(II) atom is located about an inversion centre. The mol-ecule consists of three planar units (one central square CuN(4) and two C(2)N(3) fragments), adopting a staircase-like structure. The six-membered metallocycles have a sofa conformation with the Cu atom out of the plane of the 1,3,5-triaza-penta-dienyl ligands by 0.246 (5) Å. The ipso-C atoms of the CCl(3) substituents are slightly out of the 1,3,5-triaza-penta-dienyl planes by 0.149 (6) and -0.106 (6) Å. The CCl(3) groups of each 1,3,5-triaza-penta-dienyl ligand are practically in the energetic-ally favourable mutually eclipsed conformation. In the crystal, the mol-ecules are packed in stacks along the a axis. The mol-ecules in the stacks are held together by two additional axial Cu⋯Cl inter-actions of 3.354 (2) Å. Taking the axial Cu⋯Cl inter-actions into account, the Cu(II) atom exhibits a distorted [4 + 2]-octa-hedral coordination environment. The stacks are bound to each other by weak inter-molecular attractive Cl⋯Cl [3.505 (2)-3.592 (3) Å] inter-actions.

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Project description:The title compound, C(11)H(16)Cl(4), was synthesized by the reaction of (1S)-β-pinene with triethyl-amine in the presence of ZnCl(2). The cyclo-hexene ring assumes a half-boat conformation. The crystal packing is governed only by van der Waals inter-actions. The structure, which has been refined in P2(1), presents a striking P2(1)/m pseudosymmetry.

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N,N'-Bis(2-chloro-benz-yl)-N''-(2,2,2-trichloro-acet-yl)phospho-ric triamide.

Project description:The P atom in the title compound, C(16)H(15)Cl(5)N(3)O(2)P, exhibits a tetra-hedral coordination geometry and the phosphoryl and carbonyl groups are anti with respect to one another. The dihedral angle between the benzene rings is 44.90 (15)°. One of the 2-chloro-benzyl-amido fragments is disordered over two sets of sites with occupancies of 0.8823 (17) and 0.1177 (17). In the crystal, adjacent mol-ecules are linked via N-H⋯O(P) and N-H⋯O(C) hydrogen bonds into an extended chain running parallel to the a axis.

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2,2,2-Trichloro-N-(3-nitro-phen-yl)acetamide.

Project description:In the title compound, C(8)H(5)Cl(3)N(2)O(3), the dihedral angle between the nitro-phenyl ring and the acetamide group is 5.47 (6)°. In the crystal, N-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into chains running parallel to the b axis.

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2,2,2-Trichloro-N-(3,4-dimethyl-phen-yl)acetamide.

Project description:The conformation of the N-H bond in the title compound, C(10)H(10)Cl(3)NO, is anti to the C=O bond. The amide H atom exhibits both intra-molecular N-H⋯Cl and inter-molecular N-H⋯O hydrogen bonding. The latter inter-actions link the mol-ecules into infinite chains.

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2,2,2-Trichloro-N-(2,5-dimethyl-phen-yl)acetamide.

Project description:The N-H bond in the title compound, C(10)H(10)Cl(3)NO, is syn to the 2-methyl and anti to the 5-methyl substituent of the aromatic ring. Adjacent mol-ecules are linked into chains through N-H⋯O hydrogen bonding. Two Cl atoms are each disordered equally over two sites.

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