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2-{( E )-[1-(2-Hydroxyethyl)-3,3-dimethyl-3 H -indol-1-ium-2-yl]vinyl}-6-hydroxymethyl-4-nitrophenolate dihydrate

Journal Article · · Acta Crystallographica. Section E
 [1];  [2];  [3];  [3]
  1. Sandia National Lab. (SNL-NM), Albuquerque, NM (United States); DOE/OSTI
  2. Sandia National Lab. (SNL-CA), Livermore, CA (United States)
  3. Sandia National Lab. (SNL-NM), Albuquerque, NM (United States)
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The title merocyanine-type molecule, C21H22N2O52H2O, crystallizes in a zwitterionic form and has an E configuration at the styryl C C bond. The styryl part of the molecule and the indolium ring are slightly twisted and form a dihedral angle of 13.4 (1). The 1.274 (3) A °C—O bond length in the phenolate fragment is the longest among similar molecules. Hydrogen bonds between solvent water molecules, two hydroxyl groups and the phenolate O atom dictate the packing arrangement of molecules in the crystal and join the molecules into a two-dimensional polymeric network which propagates parallel to (001). Four water molecules and four hydroxy groups form a centrosymmetric homodromic cyclic motif of O—HO hydrogen bonds. Another cyclic centrosymmetric motif is generated by four water molecules and two phenolate O atoms.

Research Organization:
Sandia National Laboratories, Albuquerque, NM (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
AC04-94AL85000
OSTI ID:
1625734
Journal Information:
Acta Crystallographica. Section E, Journal Name: Acta Crystallographica. Section E Journal Issue: 8 Vol. 65; ISSN 1600-5368
Publisher:
International Union of CrystallographyCopyright Statement
Country of Publication:
United States
Language:
English

References (7)

Structure of a new photochromic indoline spiropyran journal January 1985
Signal Processing at the Molecular Level journal May 2001
Digital Processing with a Three-State Molecular Switch journal May 2003
Proton exchange and isomerisation reactions of photochromic and reverse photochromic spiro-pyrans and their merocyanine forms journal January 1999
Mercury CSD 2.0 – new features for the visualization and investigation of crystal structures journal March 2008
A short history of SHELX journal December 2007
3-{2-[2-(3,5-Dinitro-2-oxidophenyl)ethyl]-3,3-dimethyl-3 H -indol-1-ium-1-yl}propanoic acid bis(dimethylformamide) solvate journal February 2003

Cited By (2)

Acidochromic spiropyran–merocyanine stabilisation in the solid state journal January 2018
Acidochromic spiropyran–merocyanine stabilisation in the solid state journal July 2018

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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
Crystallography