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  2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid and -benzamide: structural characterization of two precursors for antitubercular benzothiazinones

Richter, A., Goddard, R., Schlegel, T., Imming, P., & Seidel, R. W. (2021). 2-Chloro-3-nitro-5-(trifluoromethyl)benzoic acid and -benzamide: structural characterization of two precursors for antitubercular benzothiazinones. Acta Crystallographica Section E: Structure Reports Online, 77(2), 142-147. doi:10.1107/S2056989021000517.

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 Creators:
Richter, Adrian1, Author
Goddard, Richard2, Author              
Schlegel, Tom1, Author
Imming, Peter1, Author
Seidel, Rüdiger W.1, Author
Affiliations:
1Institut für Pharmazie, Martin-Luther-Universität Halle-Wittenberg, Wolfgang-Langenbeck-Str. 4, 06120 Halle (Saale), ou_persistent22              
2Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: benzothiazinones; BTZ043; PBTZ169; nitrobenzoic acids; nitrobenzamides; antituberculosis drugs; hydrogen bonds; crystal structure
 Abstract: 8-Nitro-1,3-benzothiazin-4-ones are a promising class of new antitubercular agents, two candidates of which, namely BTZ043 and PBTZ169 (INN: macozinone), have reached clinical trials. The crystal and molecular structures of two synthetic precursors, 2-chloro-3-nitro-5-(trifluoromethyl)benzoic acid, C8H3ClF3NO4 (1), and 2-chloro-3-nitro-5-(trifluoromethyl)benzamide, C8H4ClF3N2O3 (2), are reported. In 1 and 2, the respective carboxy, carboxamide and the nitro groups are significantly twisted out of the plane of the benzene ring. In 1, the nitro group is oriented almost perpendicular to the benzene ring plane. In the crystal, 1 and 2 form O—H...O and N—H...O hydrogen-bonded dimers, respectively, which in 2 extend into primary amide tapes along the [101] direction. The trifluoromethyl group in 2 exhibits rotational disorder with an occupancy ratio of 0.876 (3):0.124 (3).

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Language(s): eng - English
 Dates: 2021-01-012021-01-132021-02-01
 Publication Status: Published online
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1107/S2056989021000517
 Degree: -

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Title: Acta Crystallographica Section E: Structure Reports Online
  Other : Struct. Rep. Online
  Other : Structure Reports Online
  Abbreviation : Acta Crystallogr., Sect. E: Struct. Rep. Online
Source Genre: Journal
 Creator(s):
Affiliations:
Publ. Info: Chester, UK : International Union of Crystallography
Pages: - Volume / Issue: 77 (2) Sequence Number: - Start / End Page: 142 - 147 Identifier: ISSN: 1600-5368
CoNE: https://pure.mpg.de/cone/journals/resource/954925468297