N-(4-Meth-oxy-3-nitro-phen-yl)acetamide

James E Hines Iii; Ogad A Agu; Curtistine J Deere; Frank R Fronczek; Rao M Uppu

doi:10.1107/S2414314623002985

N-(4-Meth-oxy-3-nitro-phen-yl)acetamide

IUCrdata. 2023 Apr 4;8(Pt 4):x230298. doi: 10.1107/S2414314623002985. eCollection 2023 Apr.

Authors

James E Hines Iii¹, Ogad A Agu¹, Curtistine J Deere¹, Frank R Fronczek², Rao M Uppu¹

Affiliations

¹ Department of Environmental Toxicology, Southern University and A&M College, Baton Rouge, LA 70813, USA.
² Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA.

Abstract

The title compound, C₉H₁₀N₂O₄, crystallizes with a disordered nitro group in twinned crystals. Both the meth-oxy group and the acetamide groups are nearly coplanar with the phenyl ring, and the C-N-C-O torsion angle [0.2 (4)°] is also insignificantly different from zero. Overall, the 12-atom meth-oxy-phenyl-acetamide group is nearly planar, with an r.m.s. deviation of 0.042 Å. The nitro group is twisted out of this plane by about 30°, disordered into two orientations with opposite senses of twist. In the crystal, the N-H group donates a hydrogen bond to a nitro oxygen atom, generating chains propagating in the [101] direction. The amide carbonyl oxygen atom is not involved in the hydrogen bonding.

Keywords: N-alkoxyacetanilides; crystal structure; hydrogen bonding; nitro products; phenacetin congeners.

Grants and funding

The authors acknowledge the support from the National Institutes of Health (NIH) through the National Institute of General Medical Science (NIGMS) grant No. 5 P2O GM103424–17 and the US Department of Education (US DoE; Title III, HBGI Part B grant No. P031B040030). Its contents are solely the responsibility of authors and do not represent the official views of NIH, NIGMS, or US DoE. The upgrade of the diffractometer was made possible by grant No. LEQSF(2011–12)-ENH-TR-01, administered by the Louisiana Board of Regents.