Research Article: 4-Butyl­amino-3-nitro­benzoic acid

Date Published: May 01, 2009

Publisher: International Union of Crystallography

Author(s): Shivanagere Nagojappa Narendra Babu, Aisyah Saad Abdul Rahim, Hasnah Osman, Samuel Robinson Jebas, Hoong-Kun Fun.


The asymmetric unit of the title compound, C11H14N2O4, comprises four crystallographically independent mol­ecules (A, B, C and D) with similar geometries. In each mol­ecule, the butyl­amino side chain is in an extended conformation, and the carboxyl and butyl­amino groups are almost coplanar with the attached benzene ring; the nitro group is slightly twisted away from the benzene ring. In the asymmetric unit, the benzene rings of mol­ecules A, B and C are stacked parallel to one another, with a centroid–centroid distance of 3.6197 (11) or 3.6569 (11) Å, indicating π–π inter­actions. An intra­molecular N—H⋯O hydrogen bond is observed in each independent mol­ecule. In addition to the π–π inter­actions, the crystal packing is consolidated by inter­molecular O—H⋯O and C—H⋯O hydrogen bonds and C—H⋯π inter­actions. The crystal studied was a non-merohedral twin. The minor twin component refined to a value of 0.290 (1).

Partial Text

For the synthesis of nitro­benzoic acid derivatives, see: Ishida et al. (2006 ▶); Mohd Maidin et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).




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