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Volume 69 
Part 4 
Pages o604-o605  
April 2013  

Received 8 March 2013
Accepted 20 March 2013
Online 28 March 2013

Key indicators
Single-crystal X-ray study
T = 90 K
Mean [sigma](C-C) = 0.001 Å
R = 0.032
wR = 0.087
Data-to-parameter ratio = 27.9
Details
Open access

(Z)-1-(2-Hydroxyethyl)-4-(2-methoxybenzylidene)-2-methyl-1H-imidazol-5(4H)-one

aDepartment of Chemistry, Southern University, Baton Rouge, LA 70813, USA, and bDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
Correspondence e-mail: ffroncz@lsu.edu

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-H...N contact occurs. In the crystal, O-H...N hydrogen bonds link the molecules, forming chains along the b-axis direction. C-H...O hydrogen bonds are also observed.

Related literature

For background to green fluorescent protein, see: Shimomura et al. (1962[Shimomura, O., Johnson, F. H. & Saiga, Y. (1962). J. Cell. Comp. Physiol. 59, 223-239.]); Shimomura (2009[Shimomura, O. (2009). Angew. Chem. Int. Ed. Engl. 48, 5590-5602.]); Remington (2006[Remington, S. J. (2006). Curr. Opin. Struct. Biol. 16, 714-721.]); Tsien (1998[Tsien, R. Y. (1998). Annu. Rev. Biochem. 67, 509-544.]); Chalfie et al. (1994[Chalfie, M., Tu, Y., Euskirchen, G., Ward, W. W. & Prasher, D. C. (1994). Science, 263, 802-805.]); Prasher et al. (1992[Prasher, D. C., Eckenrode, V. K., Ward, W. W., Prendergast, F. G. & Cormier, M. J. (1992). Gene, 111, 229-233.]). For the synthesis, see: Yampolsky et al. (2005[Yampolsky, I. V., Remington, S. J., Martynov, V. I., Potapov, V. K., Lukyanov, S. & Lukyanov, K. A. (2005). Biochemistry, 44, 5788-5793.]); Bailly et al.(2004[Bailly, F., Maurin, C., Teissier, E., Vezin, H. & Cotelle, P. (2004). Bioorg. Med. Chem. 12, 5611-5618.]); Wenge & Wagenknecht (2011[Wenge, U. & Wagenknecht, H.-A. (2011). Synthesis, 3, 0502-0508.]). For related structures, see: Naumov et al. (2010[Naumov, P., Kowalik, J., Solntsev, K. M., Baldridge, A., Moon, J.-S., Kranz, C. & Tolbert, L. M. (2010). J. Am. Chem. Soc. 132, 5845-5857.]); Bhattacharjya et al. (2005[Bhattacharjya, G., Govardhan, S. & Ramanathan, G. (2005). J. Mol. Struct. 752, 98-103.]); Oshimi et al. (2002[Oshimi, K., Kubo, K., Kawasaki, A., Maekawa, K., Igarashi, T. & Sakurai, T. (2002). Tetrahedron Lett. 43, 3291-3294.]); Dong et al. (2009[Dong, J., Solntsev, K. M. & Tolbert, L. M. (2009). J. Am. Chem. Soc. 131, 662-670.]). For Bijvoet pair analysis, see: Hooft et al. (2008[Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16N2O3

  • Mr = 260.29

  • Monoclinic, P 21

  • a = 9.2188 (5) Å

  • b = 7.2767 (4) Å

  • c = 9.5620 (5) Å

  • [beta] = 93.625 (6)°

  • V = 640.16 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 90 K

  • 0.35 × 0.25 × 0.17 mm

Data collection
  • Bruker Kappa APEXII DUO CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.967, Tmax = 0.984

  • 9385 measured reflections

  • 4943 independent reflections

  • 4720 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.087

  • S = 1.06

  • 4943 reflections

  • 177 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1605 Friedel pairs

  • Flack parameter: -0.9 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3O...N2i 0.879 (16) 2.001 (16) 2.8771 (9) 174.2 (15)
C4-H4B...O1ii 0.99 2.54 3.2993 (10) 133
C9-H9...N2 0.95 2.52 3.1729 (10) 126
C14-H14A...O1iii 0.98 2.52 3.3475 (12) 141
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+1]; (ii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5304 ).


Acknowledgements

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.

References

Bailly, F., Maurin, C., Teissier, E., Vezin, H. & Cotelle, P. (2004). Bioorg. Med. Chem. 12, 5611-5618.  [CrossRef] [PubMed] [ChemPort]
Bhattacharjya, G., Govardhan, S. & Ramanathan, G. (2005). J. Mol. Struct. 752, 98-103.  [CrossRef] [ChemPort]
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chalfie, M., Tu, Y., Euskirchen, G., Ward, W. W. & Prasher, D. C. (1994). Science, 263, 802-805.  [CrossRef] [ChemPort] [PubMed] [ISI]
Dong, J., Solntsev, K. M. & Tolbert, L. M. (2009). J. Am. Chem. Soc. 131, 662-670.  [CrossRef] [PubMed] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Hooft, R. W. W., Straver, L. H. & Spek, A. L. (2008). J. Appl. Cryst. 41, 96-103.  [ISI] [CrossRef] [ChemPort] [details]
Naumov, P., Kowalik, J., Solntsev, K. M., Baldridge, A., Moon, J.-S., Kranz, C. & Tolbert, L. M. (2010). J. Am. Chem. Soc. 132, 5845-5857.  [CrossRef] [ChemPort] [PubMed]
Oshimi, K., Kubo, K., Kawasaki, A., Maekawa, K., Igarashi, T. & Sakurai, T. (2002). Tetrahedron Lett. 43, 3291-3294.  [ISI] [CSD] [CrossRef] [ChemPort]
Prasher, D. C., Eckenrode, V. K., Ward, W. W., Prendergast, F. G. & Cormier, M. J. (1992). Gene, 111, 229-233.  [CrossRef] [PubMed] [ChemPort] [ISI]
Remington, S. J. (2006). Curr. Opin. Struct. Biol. 16, 714-721.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shimomura, O. (2009). Angew. Chem. Int. Ed. Engl. 48, 5590-5602.  [CrossRef] [PubMed] [ChemPort]
Shimomura, O., Johnson, F. H. & Saiga, Y. (1962). J. Cell. Comp. Physiol. 59, 223-239.  [CrossRef] [PubMed] [ChemPort] [ISI]
Tsien, R. Y. (1998). Annu. Rev. Biochem. 67, 509-544.  [ISI] [CrossRef] [ChemPort] [PubMed]
Wenge, U. & Wagenknecht, H.-A. (2011). Synthesis, 3, 0502-0508.
Yampolsky, I. V., Remington, S. J., Martynov, V. I., Potapov, V. K., Lukyanov, S. & Lukyanov, K. A. (2005). Biochemistry, 44, 5788-5793.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o604-o605   [ doi:10.1107/S1600536813007770 ]

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