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Volume 68 
Part 11 
Page o3173  
November 2012  

Received 4 October 2012
Accepted 10 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 233 K
Mean [sigma](C-C) = 0.003 Å
R = 0.036
wR = 0.099
Data-to-parameter ratio = 8.3
Details
Open access

L-Tyrosine isopropyl ester

aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, 4-72 Colombia, and bInstitute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria
Correspondence e-mail: arquevedop@unal.edu.co

The title compound, C12H17NO3, adopts a folded conformation with a C-C(NH2)-C(=O)-O torsion angle of -95.9 (2)°. In the crystal, molecules are linked by an O-H...N hydrogen bond, forming helical chains along the b-axis direction. Weak N-H...O and C-H...O hydrogen bonds are observed between the chains.

Related literature

For information about tyrosine alkyl esters as prodrugs and the structure and intermolecular interactions of L-tyrosine methyl ester compared to L-tyrosine and its ethyl and n-butyl esters, see: Nicolaï et al. (2011[Nicolaï, B., Mahé, N., Céolin, R., Rietveld, I., Barrio, M. & Tamarit, J.-L. (2011). Struct. Chem. 22, 649-659.]). For the n-butyl analogue, see: Qian et al. (2006[Qian, S.-S., Zhu, H.-L. & Tiekink, E. R. T. (2006). Acta Cryst. E62, o882-o884.]). For macrocyclization of tyrosine alkyl esters with formaldehyde, see: Quevedo & Moreno-Murillo (2009[Quevedo, R. & Moreno-Murillo, B. (2009). Tetrahedron Lett. 50, 936-938.]); Nuñez-Dallos et al. (2012[Nuñez-Dallos, N., Reyes, A. & Quevedo, R. (2012). Tetrahedron Lett. 53, 530-533.]). For a related structure of tyramine, see: Quevedo et al. (2012[Quevedo, R., Nuñez-Dallos, N., Wurst, K. & Duarte-Ruiz, A. (2012). J. Mol. Struct. 1029, 175-179.]).

[Scheme 1]

Experimental

Crystal data
  • C12H17NO3

  • Mr = 223.27

  • Orthorhombic, P 21 21 21

  • a = 5.4539 (1) Å

  • b = 14.0521 (3) Å

  • c = 16.5163 (4) Å

  • V = 1265.79 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 233 K

  • 0.4 × 0.3 × 0.2 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 8375 measured reflections

  • 1318 independent reflections

  • 1271 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.099

  • S = 1.07

  • 1318 reflections

  • 158 parameters

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

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3O...N1i 0.97 (4) 1.78 (4) 2.736 (3) 167 (3)
N1-H1N...O3ii 0.88 (2) 2.27 (2) 3.106 (2) 157 (2)
N1-H2N...O3iii 0.89 (3) 2.46 (3) 3.336 (3) 171 (2)
C2-H2...O1iv 0.99 2.37 3.314 (3) 159
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]; (iii) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) x+1, y, z.

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp 307-326. New York: Academic Press.]) and SCALEPACK; 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: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5203 ).


Acknowledgements

We thank the Universidad Nacional de Colombia for the financial support (DIB research project No. 14178).

References

Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Nicolaï, B., Mahé, N., Céolin, R., Rietveld, I., Barrio, M. & Tamarit, J.-L. (2011). Struct. Chem. 22, 649-659.
Nonius (1998). COLLECT. Nonius BV Delft, The Netherlands.
Nuñez-Dallos, N., Reyes, A. & Quevedo, R. (2012). Tetrahedron Lett. 53, 530-533.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp 307-326. New York: Academic Press.
Qian, S.-S., Zhu, H.-L. & Tiekink, E. R. T. (2006). Acta Cryst. E62, o882-o884.  [CSD] [CrossRef] [details]
Quevedo, R. & Moreno-Murillo, B. (2009). Tetrahedron Lett. 50, 936-938.  [ISI] [CrossRef] [ChemPort]
Quevedo, R., Nuñez-Dallos, N., Wurst, K. & Duarte-Ruiz, A. (2012). J. Mol. Struct. 1029, 175-179.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3173  [ doi:10.1107/S1600536812042377 ]

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