5-(Methoxycarbonyl)thiophene-2-carboxylic acid

Xia, Guangming; Ji, Muwei; Lü, Ping; Sun, Guangmin; Xu, Wenfang

doi:10.1107/s1600536809053161

Cited by 6 publications

(1 citation statement)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Such differences also appear between carboxyl group and thiophene ring, with 2.8(2)°, 0.9(4)°and 9.4(1)°, respectively. In the thiophene ring the C-S distances are in the range of 1.705(2)-1.712(2) Å and the C-S-C angles are in the range of 90.5-90.7°, similar to other 2-thiophenecarboxylic acid compounds [2,3]. In the title structure, all molecules are connected to hydrogen-bonded dimers.…”

Section: Discussionmentioning

confidence: 53%

Crystal structure of 4-phenyl-5-(trifluoromethyl)-thiophene-2-carboxylic acid, C12H7F3O2S

Zhu

Zhang

Shi

2013

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

Source of material 4-Phenyl-5-(trifluoromethyl)thiophene-2-carboxylic acid was prepared by using 1,1,1-trifluoro-3-phenylpropan-2-one, phosphorous oxychloride and methyl 2-mercaptoacetate as raw materials according to the method of literature [1]. The colorless block-shaped crystals suitable for X-ray diffraction were obtained by slow evaporation of a methanol solution for a few days. Experimental detailsHydrogen atomes were positioned geometrically and allowed to ride on theier parent atoms with C-H = 0.93 Å, except for H1, H3 and H5 (U iso (H) = 1.2U eq (parent atom)).Discussion 2-Thiophenecarboxylic acid and its derivatives are important pharmaceutical intermediates [1]. In the crystal structure of the title compound, there are three crystallographically independent molecules. The bond distances and angles in these molecules are essentially the same within experimental error, but the dihedral angles between the phenyl and thiophene rings in these molecules display differences, with 43.10(8)°, 44.95(8)°and 38.99(9)°, respectively. Such differences also appear between carboxyl group and thiophene ring, with 2.8(2)°, 0.9(4)°and 9.4(1)°, respectively. In the thiophene ring the C-S distances are in the range of 1.705(2)-1.712(2) Å and the C-S-C angles are in the range of 90.5-90.7°, similar to other 2-thiophenecarboxylic acid compounds [2,3]. In the title structure, all molecules are connected to hydrogen-bonded dimers. Two crystallographic independent molecules are linked to each other with O1-H1···O4 (O···O = 2.640(2) Å, angle 174(3)°) and O3-H3···O2 (O···O = 2.646(2) Å, angle 178(3)°) form an asymmetric dimer. The third crystallographic independent molecule forms a dimer with a symmetry related molecule O5-H5···O6 (-x+1, -y+1, -z+1; O···O = 2.638(2) Å, O-H···O = 176(3)°).

show abstract

Section: Discussionmentioning

confidence: 53%

Crystal structure of 4-phenyl-5-(trifluoromethyl)-thiophene-2-carboxylic acid, C12H7F3O2S

Zhu

Zhang

Shi

2013

Zeitschrift Für Kristallographie - New Crystal Structures

View full text Add to dashboard Cite

show abstract

Dimethyl 3,3′-diphenyl-2,2′-[(S)-thiophene-2,5-diylbis(carbonylazanediyl)]dipropanoate

Xia

Liu

et al. 2010

Acta Cryst E

Self Cite

View full text Add to dashboard Cite

The asymmetric unit of the title compound, C26H26N2O6S, contains two independent molecules; each has twofold symmetry with the S atom and the mid-point of the C—C bond of the thiophene ring located on a twofold rotation axis. In the two molecules, the terminal benzene rings are oriented at dihedral angles of 65.8 (3) and 63.5 (3)° with respect to the central thiophene rings. The methoxycarbonyl group of one molecule is disordered over two positions with site-occupancy factors of 0.277 (12) and 0.723 (12). Intermolecular N—H⋯O hydrogen bonding is present in the crystal structure.

show abstract