The Structure of Crystalline Agnotobenzaldehyde

Wayland E. Noland, Glen C. Gullickson, Henrik van Lengerich, Paul J. Erdman, Kenneth J. Tritch

Research output: Contribution to journalArticlepeer-review

Abstract

Abstract: Agnotobenzaldehyde was first reported by Dr. Eugen Bamberger in 1906, from a Zn-promoted reduction of 2-nitrobenzaldehyde. He determined the empirical formula to be C14H12N2O5. Subsequent work determined the chemical structure of the solution form by IR and NMR analysis, but the structure of the crystal form remained inconclusive. In the present work, the structure of crystalline agnotobenzaldehyde has been found to be rac-(3R)-1-[(S)-hydroxy(2-nitrophenyl)methyl]-1,3-dihydro-2,1-benzisoxazol-3-ol. Crystals are orthorhombic with the Pbca space group. At 173(2) K, a = 13.8066(14), b = 8.4412(9), c = 22.832(2) Å, and V = 2660.9(5) Å3 with Z = 8. Poly(O–H⋯) C4 4(8) chains of alternating intra- and inter-molecular hydrogen bonds form along the b axis. These chains probably affect the regio- and diastereo-specificity of cyclization. Graphical Abstract: The crystalline form of agnotobenzaldehyde has a different molecular structure than the solution form, and features hydrogen bond chains that probably control the stereo- and regio-specificity of the hydroxyl and isoxazole moieties. [Figure not available: see fulltext.].

Original languageEnglish (US)
Pages (from-to)80-85
Number of pages6
JournalJournal of Chemical Crystallography
Volume47
Issue number3-4
DOIs
StatePublished - Aug 1 2017

Keywords

  • Hydrogen-bonding
  • Nitrogen heterocycles
  • Reduction
  • Zinc

Fingerprint Dive into the research topics of 'The Structure of Crystalline Agnotobenzaldehyde'. Together they form a unique fingerprint.

Cite this