Synthesis and crystal structures of 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde) and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde)

Journal Article · Thu Nov 22 00:00:00 EST 2018 · Acta Crystallographica. Section E, Crystallographic Communications

DOI:https://doi.org/10.1107/S2056989018016316· OSTI ID:1630006

Sausa, Rosario C. ^[1]; Lastovickova, Dominika N. ^[2]; La Scala, John J. ^[3]

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1. US Army Research Laboratory, RDRL-WML-B, Aberdeen Proving Ground, MD (United States)
2. US Army Research Laboratory, RDRL-WML-G, Aberdeen Proving Ground, MD (United States). Also an ORISE Postdoctoral Research Fellow
3. US Army Research Laboratory, RDRL-WML-G, Aberdeen Proving Ground, MD (United States)

The title compounds 5,5'-(propane-2,2-diyl)bis(2-hydroxybenzaldehyde), C₁₇H₁₆O₄, (1), and 5,5'-(propane-2,2-diyl)bis(2-hydroxyisophthalaldehyde), C₁₉H₁₆O₆, (2), crystallize with one molecule in the asymmetric unit. In molecule (1), a >C(CH₃)₂group bridges two nearly planar salicylaldehyde groups [r.m.s deviations = 0.010 (1) and 0.025 (2) Å], each comprising a planar phenyl ring bonded with a hydroxyl and an aldehyde group. Similarly, compound (2) has the same bridging group, but it connects two nearly planar appendants [r.m.s deviations = 0.034 (1) and 0.035 (1) Å], each comprising a phenyl ring bonded with a hydroxyl and two aldehyde groups. Molecule (1) exhibits a bridge angle of 109.5 (2)° with the salicylaldehyde planes subtending a dihedral angle of 88.4 (1)°. In contrast, molecule (2) presents a bridge angle of 108.9 (2)° with its appendants subtending a dihedral angle of 79.6 (3)°. Both molecules exhibit two intramolecular O—H...O hydrogen bonds involving the phenolic H atoms and carboxyl O-atom acceptors. In the crystal of (2), O—H...O hydrogen bonds between one of the hydroxyl H atoms and a carboxyl O atom from a symmetry-related molecule form a chain along [10\overline{1}]. In addition, (2) exhibits a strong visible luminescence when excited with ultraviolet radiation.

• Research Organization: Oak Ridge Inst. for Science and Education (ORISE), Oak Ridge, TN (United States)
• Sponsoring Organization: USDOE
• Grant/Contract Number: SC0014664
• OSTI ID: 1630006
• Journal Information: Acta Crystallographica. Section E, Crystallographic Communications, Vol. 74, Issue 12; ISSN 2056-9890
• Publisher: International Union of Crystallography
• Country of Publication: United States
• Language: English