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

Praveen, A.S.; Jasinski, J.P.; Golen, J.A.; Yathirajan, H.S.; Narayana, B.

doi:10.1107/S1600536811054493

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 (C-C) = 0.002 Å
R = 0.047
wR = 0.132
Data-to-parameter ratio = 24.0
Details

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

A. S. Praveen,^a Jerry P. Jasinski,^b ^* James A. Golen,^b H. S. Yathirajan ^a and B. Narayana ^c

^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-HO hydrogen bonds. Weak C-HO 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). For barbitone, the first barbiturate hypnotic sedative, see: Russell (1945). For the similarity of related N-substituted 2-arylacetamides to the lateral chain of natural benzylpenicillin, see: Mijin & Marinkovic (2006); Mijin et al. (2008). For the coordination abilities of amides, see: Wu et al. (2008, 2010). For related structures, see: John et al. (2010); Nogueira et al. (2010); Praveen et al. (2011); Selig et al. (2010); Wen et al. (2010). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₅H₁₇N₃O₃
M_r = 287.32
Triclinic, $[P \overline 1]$
a = 7.1536 (6) Å
b = 8.2070 (7) Å
c = 13.8259 (10) Å
= 74.420 (7)°
= 86.540 (6)°
= 69.186 (8)°
V = 730.30 (10) Å³
Z = 2
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.961, T_max = 0.980
8350 measured reflections
4735 independent reflections
3887 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(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
_max = 0.37 e Å^-3
_min = -0.22 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3NO3ⁱ	0.875 (15)	1.979 (15)	2.8535 (12)	176.0 (14)
C3-H3O2ⁱⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
John, P., Ahmad, W., Khan, I. U., Sharif, S. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2048.
Mijin, D. & Marinkovic, A. (2006). Synth. Commun. 36, 193-198.
Mijin, D. Z., Prascevic, M. & Petrovic, S. D. (2008). J. Serb. Chem. Soc. 73, 945-950.
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.
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.
Russell, J. A. (1945). Annu. Rev. Biochem. 14, 309-332.
Selig, R., Schollmeyer, D., Albrecht, W. & Laufer, S. (2010). Acta Cryst. E66, o1132.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wen, Y.-H., Qin, H.-Q. & Wen, H.-L. (2010). Acta Cryst. E66, o3294.
Wu, W.-N., Cheng, F.-X., Yan, L. & Tang, N. (2008). J. Coord. Chem. 61, 2207- 2215.
Wu, W.-N., Wang, Y., Zhang, A.-Y., Zhao, R.-Q. & Wang, Q.-F. (2010). Acta Cryst. E66, m288.

organic compounds