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Volume 69 
Part 10 
Pages o1577-o1578  
October 2013  

Received 17 September 2013
Accepted 18 September 2013
Online 21 September 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.141
Data-to-parameter ratio = 18.8
Details
Open access

tert-Butyl 4-{[2-amino-4-(2-hydroxyphenyl)pyrimidin-5-yl]methyl}piperazine-1-carboxylate

aP. S. Science and H. D. Patel Arts College, S. V. Campus, Kadi, Gujarat, 382 715, India,bDepartment of Physics, Bhavan's Sheth R. A. College of Science, Ahmedabad, Gujarat, 380 001, India, and cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: Edward.Tiekink@gmail.com

In the title compound, C20H27N5O3, the central piperazine ring adopts a chair conformation, with the N-bound carboxylate and methylene substituents occupying bisectional and equatorial orientations, respectively. A twist is evident between the aromatic rings [dihedral angle = 25.61 (9)°] but an intramolecular O-H...N hydrogen bond persists between these. Supramolecular tapes along [1-10] are formed in the crystal packing through N(amino)-H...O(hydroxyl) and N(amino)-H...N(pyrimidinyl) hydrogen bonds, and these are linked into layers in the ab plane by [pi]-[pi] interactions [inter-centroid distance between pyrimidinyl rings = 3.5919 (9) Å].

Related literature

For the biological activity of pyrimidine-containing heterocyclic compounds, see: Topalis et al. (2011[Topalis, D., Pradere, U., Roy, V., Caillat, C., Azzouzi, A., Broggi, J., Andrei, G., Lin, L., Eriksson, S., Alexandre, J. A. C., El-Amri, C., Deville-Bonne, D., Meyer, P., Balzarini, J. & Agrofoglio, L. A. (2011). J. Med. Chem. 54, 222-232.]); Sbardella et al. (2011[Sbardella, G., Mai, A., Bartolini, S., Castellano, S., Cirilli, R., Rotili, D., Milite, C., Santoriallo, M., Orlando, S., Sciamanna, I., Serafino, A., Lavia, P. & Spadafora, C. (2011). J. Med. Chem. 54, 5927-5936.]); Zhang et al. (2011[Zhang, Z., Wallace, M. B., Feng, J., Stefford, J. A., Skene, R. J., Shi, L., Lee, B., Aertgeerts, K., Jennings, A., Xu, R., Kassel, D. B., Kaldor, S. W., Navre, M., Webb, D. R. & Gwaltney, S. L. (2011). J. Med. Chem. 54, 510-524.]). For the synthesis, see: Patel et al. (2011[Patel, M. C., Gajera, N. N. & Rajani, D. P. (2011). Pharma Chem. 3, 422-432.]).

[Scheme 1]

Experimental

Crystal data
  • C20H27N5O3

  • Mr = 385.47

  • Monoclinic, P 21 /n

  • a = 6.1925 (2) Å

  • b = 8.2636 (2) Å

  • c = 40.7287 (11) Å

  • [beta] = 93.513 (2)°

  • V = 2080.27 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.47 × 0.35 × 0.31 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SADABS and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.997

  • 20251 measured reflections

  • 4985 independent reflections

  • 3339 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.141

  • S = 1.04

  • 4984 reflections

  • 265 parameters

  • 3 restraints

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

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H1O...N4 0.83 (1) 1.80 (2) 2.560 (2) 151 (3)
N5-H1N...N3i 0.86 (1) 2.19 (1) 3.054 (2) 179 (2)
N5-H2N...O3ii 0.86 (1) 2.29 (1) 3.139 (2) 169 (2)
Symmetry codes: (i) -x+3, -y+1, -z; (ii) -x+2, -y+2, -z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SADABS and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SADABS 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.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5347 ).


Acknowledgements

The authors are grateful to the Department of Science and Technology (DST), and SAIF, IIT Madras, Chennai, India, for the X-ray data collection. MCP is thankful to the University Grant Commission, New Delhi, India, for research funding under research project No. 39-715/2010(SR). The authors also thank the Ministry of Higher Education, Malaysia, for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/03).

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2004). APEX2, SADABS and SAINT, Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Patel, M. C., Gajera, N. N. & Rajani, D. P. (2011). Pharma Chem. 3, 422-432.  [ChemPort]
Sbardella, G., Mai, A., Bartolini, S., Castellano, S., Cirilli, R., Rotili, D., Milite, C., Santoriallo, M., Orlando, S., Sciamanna, I., Serafino, A., Lavia, P. & Spadafora, C. (2011). J. Med. Chem. 54, 5927-5936.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Topalis, D., Pradere, U., Roy, V., Caillat, C., Azzouzi, A., Broggi, J., Andrei, G., Lin, L., Eriksson, S., Alexandre, J. A. C., El-Amri, C., Deville-Bonne, D., Meyer, P., Balzarini, J. & Agrofoglio, L. A. (2011). J. Med. Chem. 54, 222-232.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Zhang, Z., Wallace, M. B., Feng, J., Stefford, J. A., Skene, R. J., Shi, L., Lee, B., Aertgeerts, K., Jennings, A., Xu, R., Kassel, D. B., Kaldor, S. W., Navre, M., Webb, D. R. & Gwaltney, S. L. (2011). J. Med. Chem. 54, 510-524.  [Web of Science] [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o1577-o1578   [ doi:10.1107/S1600536813025774 ]

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