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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 · · Acta Crystallographica. Section E, Crystallographic Communications
 [1];  [2];  [3]
  1. US Army Research Laboratory, RDRL-WML-B, Aberdeen Proving Ground, MD (United States); US Army Research Lab
  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)
+ Show Author Affiliations

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 Institute 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, Journal Name: Acta Crystallographica. Section E, Crystallographic Communications Journal Issue: 12 Vol. 74; ISSN ACSECI; ISSN 2056-9890
Publisher:
International Union of CrystallographyCopyright Statement
Country of Publication:
United States
Language:
English

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