Intramolecular and intermolecular geometry of thiophenes with oxygen-containing substituents

Blake, Alexander J.; Clark, Bernard A. J.; Gierens, Hedi; Gould, Robert O.; Hunter, George; McNab, Hamish; Morrow, Mark; Sommerville, Craig C.

doi:10.1107/s0108768199003547

Cited by 16 publications

(20 citation statements)

References 10 publications

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“…We present here the structure of 3-acetylthiophene, (I), and compare it with those of two simple 3-substituted thiophenes, i.e. 3-methoxythiophene, (II) (refcode GUFJEW; Blake et al, 1999), and 3-thiophenecarboxylic acid, (III) [refcodes THIPAC (Hudson & Robertson, 1964) and THIPAC01 (Roux et al, 2003)].…”

Section: Commentmentioning

confidence: 99%

1-(Thiophen-3-yl)ethanone

2011

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The structure of the title compound, C(6)H(6)OS, exhibits a flip-type disorder of the thiophene ring [occupancy ratio = 0.848 (3):0.152 (3)], which is typical for many thiophene derivatives. The puckered thiophene ring is essentially coplanar with the plane formed by the non-H atoms of the acetyl substituent, similar to its simple analogues, i.e. 3-acetyl-2-carboxythiophene, 4-acetyl-3-carboxythiophene and 3,5-diacetyl-2-ethylamino-4-methylthiophene. In the crystal structure, molecules are connected by C-H···π hydrogen bonds, forming a sheet parallel to the (001) plane. Moreover, an inspection of the crystal lattice reveals that there are short S···O contacts connecting the molecules of adjacent sheets. Comparison of the title crystal structure with its simple 3-methoxythiophene analogue shows a close similarity in the herringbone arrangement of molecules and in the presence of C-H···π interactions and S···O contacts.

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Section: Commentmentioning

confidence: 99%

1-(Thiophen-3-yl)ethanone

2011

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“…The molecular diagrams given to the participants in the CSP workshops (I±III, VII for CSP1999; IV±VI for CSP2001). Experimental structures references: I (Boese & Garbarczyk, 1998), II (Blake et al, 1999), III (Clegg et al, 2001), IV (Howie & Skakle, 2001), V (Fronczek & Garcia, 2001), VI (Hursthouse, 2001), VII (Boese et al, 1999).…”

Section: Figurementioning

confidence: 99%

Crystal structure prediction of small organic molecules: a second blind test

Motherwell

Ammon

Dunitz

et al. 2002

Acta Crystallogr B Struct Sci

370

266

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The first collaborative workshop on crystal structure prediction (CSP1999) has been followed by a second workshop (CSP2001) held at the Cambridge Crystallographic Data Centre. The 17 participants were given only the chemical diagram for three organic molecules and were invited to test their prediction programs within a range of named common space groups. Several different computer programs were used, using the methodology wherein a molecular model is used to construct theoretical crystal structures in given space groups, and prediction is usually based on the minimum calculated lattice energy. A maximum of three predictions were allowed per molecule. The results showed two correct predictions for the first molecule, four for the second molecule and none for the third molecule (which had torsional flexibility). The correct structure was often present in the sorted low-energy lists from the participants but at a ranking position greater than three. The use of non-indexed powder diffraction data was investigated in a secondary test, after completion of the ab initio submissions. Although no one method can be said to be completely reliable, this workshop gives an objective measure of the success and failure of current methodologies.

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“…Molecular diagrams of the organic compounds presented to the authors in December 1998 for crystal structure prediction. (I): 3-oxabicyclo(3.2.0)hepta-1,4-diene (Boese & Garbarczyk, 1998); (II): 4-hydroxy-2-thiophenecarbonitrile (Blake et al, 1999); (III): 2-(2-phenylethenyl)-1,3,2-benzodioxaborole (Clegg & Scott, 1998); propane (Boese et al, 1999a,b).…”

Section: Figurementioning

confidence: 99%

A test of crystal structure prediction of small organic molecules

Lommerse

Motherwell

Ammon

et al. 2000

Acta Crystallogr B Struct Sci

410

295

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A collaborative workshop was held in May 1999 at the Cambridge Crystallographic Data Centre to test how well currently available methods of crystal structure prediction perform when given only the atomic connectivity for an organic compound. A blind test was conducted on a selection of four compounds and a wide range of methodologies representing, the principal computer programs currently available were used. There were 11 participants who were allowed to propose at most three structures for each compound. No program gave consistently reliable results. However, seven proposed structures were close to an experimental one and were classified as "correct". One compound occurred in two polymorphs, but only one form was predicted correctly among the calculated structures. The basic problem with lattice energy based methods of crystal structure prediction is that many structures are found within a few kJ mol(-1) of the global minimum. The fine detail of the force-field methodology and parametrization influences the energy ranking within each method. Nevertheless, present methods may be useful in providing a set of structures as possible polymorphs for a given molecular structure.

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Intramolecular and intermolecular geometry of thiophenes with oxygen-containing substituents

Cited by 16 publications

References 10 publications

1-(Thiophen-3-yl)ethanone

1-(Thiophen-3-yl)ethanone

Crystal structure prediction of small organic molecules: a second blind test

A test of crystal structure prediction of small organic molecules

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