rac- N-(4-Eth-oxy-phen-yl)-3-hy-droxy-butanamide

James E Hines Iii; Zechariah Myles; Garrick Breaux; Frank R Fronczek; Rao M Uppu

doi:10.1107/S2414314623002316

rac- N-(4-Eth-oxy-phen-yl)-3-hy-droxy-butanamide

IUCrdata. 2023 Mar 15;8(Pt 3):x230231. doi: 10.1107/S2414314623002316. eCollection 2023 Mar.

Authors

James E Hines Iii¹, Zechariah Myles¹, Garrick Breaux¹, 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

In the title compound, racemic bucetin [systematic name: N-(4-eth-oxy-phen-yl)-3-hydroxy-butanamide], C₁₂H₁₇NO₃, the mol-ecule is in an extended conformation as illustrated by the C-O-C-C torsion angle [170.14 (15)°] in the eth-oxy group and the subsequent C-N-C-C [-177.24 (16)°], N-C-C-C [170.08 (15)°] and C-C-C-C [171.41 (15)°] torsion angles in the butanamide chain. In the crystal, the O-H group donates an inter-molecular O-H⋯O hydrogen bond to the amide carbonyl oxygen atom and also accepts an inter-molecular N-H⋯O hydrogen bond from an adjacent N-H group. The former forms 12-membered dimeric rings about inversion centers, and the latter form chains in the [001] direction. The overall hydrogen-bonded network is two-dimensional, with no propagation in the [100] direction.

Keywords: bucetin; crystal structure; hydrogen bonding; non-opioid analgesics.

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 GM103424–20 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.