Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 2 (February 2013)


organic compounds



Acta Cryst. (2013). C69, 162-171    [ doi:10.1107/S0108270112051049 ]

Six closely related 4,6-disubstituted 2-amino-5-formyl­pyrimidines: different ring conformations, polarized electronic structures, and hydrogen-bonded assembly in zero, one, two and three dimensions

L. M. Acosta, A. F. Yepes, A. Palma, J. Cobo and C. Glidewell

Abstract: In each of ethyl N-{2-amino-5-formyl-6-[meth­yl(phen­yl)amino]­pyrimidin-4-yl}glycinate, C16H19N5O3, (I), N-{2-amino-5-formyl-6-[meth­yl(phen­yl)amino]­pyrimidin-4-yl}glycin­amide, C14H16N6O2, (II), and ethyl 3-amino-N-{2-amino-5-formyl-6-[meth­yl(phen­yl)amino]­pyrimidin-4-yl}propionate, C17H21N5O3, (III), the pyrimidine ring is effectively planar, but in each of methyl N-{2-amino-6-[benz­yl(meth­yl)amino]-5-formyl­pyrimidin-4-yl}glycinate, C16H19N5O3, (IV), ethyl 3-amino-N-{2-amino-6-[benz­yl(meth­yl)amino]-5-formylpyrimidin-4-yl}propionate, C18H23N5O3, (V), and ethyl 3-amino-N-[2-amino-5-formyl-6-(piperidin-4-yl)pyrimidin-4-yl]propionate, C15H23N5O3, (VI), the pyrimidine ring is folded into a boat conformation. The bond lengths in each of (I)-(VI) provide evidence for significant polarization of the electronic structure. The mol­ecules of (I) are linked by paired N-H...N hydrogen bonds to form isolated dimeric aggregates, and those of (III) are linked by a combination of N-H...N and N-H...O hydrogen bonds into a chain of edge-fused rings. In the structure of (IV), mol­ecules are linked into sheets by means of two hydrogen bonds, both of N-H...O type, in the structure of (V) by three hydrogen bonds, two of N-H...N type and one of C-H...O type, and in the structure of (VI) by four hydrogen bonds, all of N-H...O type. Mol­ecules of (II) are linked into a three-dimensional framework structure by a combination of three N-H...O hydrogen bonds and one C-H...O hydrogen bond.

Formula: C16H19N5O3, C14H16N6O2, C17H21N5O3, C18H23N5O3 and C15H23N5O3


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Structure factor file (CIF format) (147.5 kbytes)
[ doi:10.1107/S0108270112051049/yf3022Isup2.hkl ]
Contains datablock I


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Structure factor file (CIF format) (130.6 kbytes)
[ doi:10.1107/S0108270112051049/yf3022IIsup3.hkl ]
Contains datablock II


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Structure factor file (CIF format) (155.1 kbytes)
[ doi:10.1107/S0108270112051049/yf3022IIIsup4.hkl ]
Contains datablock III


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Structure factor file (CIF format) (147.9 kbytes)
[ doi:10.1107/S0108270112051049/yf3022IVsup5.hkl ]
Contains datablock IV


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Structure factor file (CIF format) (160.5 kbytes)
[ doi:10.1107/S0108270112051049/yf3022Vsup6.hkl ]
Contains datablock V


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Structure factor file (CIF format) (158.3 kbytes)
[ doi:10.1107/S0108270112051049/yf3022VIsup7.hkl ]
Contains datablock VI


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