Received 8 March 2013
In the title compound, C14H16N2O3, an analog of the chromophore in green fluorescent protein, the methoxyphenyl substituent and the imidazole N adopt a Z conformation with respect to the C=C bond. Aside from the hydroxyethyl group, the molecule is approximately planar, with the five- and six-membered ring planes forming a dihedral angle of 9.3 (1)°. An intramolecular C-HN contact occurs. In the crystal, O-HN hydrogen bonds link the molecules, forming chains along the b-axis direction. C-HO hydrogen bonds are also observed.
For background to green fluorescent protein, see: Shimomura et al. (1962); Shimomura (2009); Remington (2006); Tsien (1998); Chalfie et al. (1994); Prasher et al. (1992). For the synthesis, see: Yampolsky et al. (2005); Bailly et al.(2004); Wenge & Wagenknecht (2011). For related structures, see: Naumov et al. (2010); Bhattacharjya et al. (2005); Oshimi et al. (2002); Dong et al. (2009). For Bijvoet pair analysis, see: Hooft et al. (2008).
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5304 ).
This research was made possible by a grant supplied by the National Science Foundation's Early CAREER program (Cooperative Agreement DMR-0449886)and by the National Science Foundations HBCU-RISE program (Cooperative Agreement HRD-1036588) at Southern University. The purchase of the NMR was made possible by the National Science Foundation's Major Research Instrument program (Cooperative Agreement CHE-0321591) at Southern University. The purchase of the FTIR at Southern University was made possible by the support from Louisiana Board of Regents (grant No. LEQSF(2005-2007)-ENH-TR-65). We also want to thank the US Department of Education: Title III Part B HBGI program (grant No. P031B040030) at Southern University. Upgrade of the diffractometer at LSU was made possible by grant No. LEQSF(2011-12)-ENH-TR-01, administered by the Louisiana Board of Regents.
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