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Volume 68 
Part 1 
Pages o226-o227  
January 2012  

Received 18 December 2011
Accepted 18 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.132
Data-to-parameter ratio = 24.0
Details
Open access

N-(4,6-Dimethoxypyrimidin-2-yl)-2-(3-methylphenyl)acetamide

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri, 574 199, India
Correspondence e-mail: jjasinski@keene.edu

In the title compound, C15H17N3O3, the dihedral angle between the pyrimidine and benzene rings is 87.0 (7)°. In the crystal, molecules are linked into inversion dimers with R22(8) graph-set motifs by a pair of N-H...O hydrogen bonds. Weak C-H...O hydrogen bonds and intermolecular [pi]-[pi] interactions [centroid-centroid distance = 3.544 (1) Å] are also observed.

Related literature

For the pyrimidine ring in vitamins, see: Cox (1968[Cox, R. A. (1968). Q. Rev. Chem. Soc. 22, 499-526.]). For barbitone, the first barbiturate hypnotic sedative, see: Russell (1945[Russell, J. A. (1945). Annu. Rev. Biochem. 14, 309-332.]). For the similarity of related N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006[Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.]); Mijin et al. (2008[Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.]). For the coordination abilities of amides, see: Wu et al. (2008[Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207- 2215.], 2010[Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.]). For related structures, see: John et al. (2010[John, P., Ahmad, W., Khan, I. U., Sharif, S. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2048.]); Nogueira et al. (2010[Nogueira, T. C. M., Souza, M. V. N. de, Wardell, J. L., Wardell, S. M. S. V. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o177.]); Praveen et al. (2011[Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1826.]); Selig et al. (2010[Selig, R., Schollmeyer, D., Albrecht, W. & Laufer, S. (2010). Acta Cryst. E66, o1132.]); Wen et al. (2010[Wen, Y.-H., Qin, H.-Q. & Wen, H.-L. (2010). Acta Cryst. E66, o3294.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C15H17N3O3

  • Mr = 287.32

  • Triclinic, [P \overline 1]

  • a = 7.1536 (6) Å

  • b = 8.2070 (7) Å

  • c = 13.8259 (10) Å

  • [alpha] = 74.420 (7)°

  • [beta] = 86.540 (6)°

  • [gamma] = 69.186 (8)°

  • V = 730.30 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 173 K

  • 0.42 × 0.34 × 0.22 mm

Data collection
  • Oxford Diffraction Xcalibur Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.961, Tmax = 0.980

  • 8350 measured reflections

  • 4735 independent reflections

  • 3887 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.132

  • S = 1.02

  • 4735 reflections

  • 197 parameters

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

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3N...O3i 0.875 (15) 1.979 (15) 2.8535 (12) 176.0 (14)
C3-H3...O2ii 0.93 2.52 3.4459 (12) 177
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+1, -y+2, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5034 ).


Acknowledgements

ASP thanks the UoM for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Cox, R. A. (1968). Q. Rev. Chem. Soc. 22, 499-526.  [CrossRef] [ChemPort]
John, P., Ahmad, W., Khan, I. U., Sharif, S. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2048.  [CSD] [CrossRef] [details]
Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.  [ISI] [CrossRef] [ChemPort]
Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.  [ISI] [CrossRef] [ChemPort]
Nogueira, T. C. M., Souza, M. V. N. de, Wardell, J. L., Wardell, S. M. S. V. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o177.  [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Praveen, A. S., Jasinski, J. P., Golen, J. A., Narayana, B. & Yathirajan, H. S. (2011). Acta Cryst. E67, o1826.  [CSD] [CrossRef] [details]
Russell, J. A. (1945). Annu. Rev. Biochem. 14, 309-332.  [CrossRef] [ChemPort]
Selig, R., Schollmeyer, D., Albrecht, W. & Laufer, S. (2010). Acta Cryst. E66, o1132.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wen, Y.-H., Qin, H.-Q. & Wen, H.-L. (2010). Acta Cryst. E66, o3294.  [CSD] [CrossRef] [details]
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207- 2215.  [ISI] [CrossRef] [ChemPort]
Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o226-o227   [ doi:10.1107/S1600536811054493 ]

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