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Crystal structure of methyl 4-(4-hy ­ droxy ­ phen ­ yl)-6-methyl-2-oxo-1,2,3,4-tetra ­ hydro ­ pyrimidine-5-carboxyl ­ ate monohydrate

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ABSTRACT

The title hydrate, C13H14N2O4·H2O, crystallizes with two formula units in the asymmetric unit (Z′ = 2). The dihedral angles between the planes of the tetra­hydro­pyrimidine ring and the 4-hy­droxy­phenyl ring and ester group are 86.78 (4) and 6.81 (6)°, respectively, for one mol­ecule and 89.35 (4) and 3.02 (4)° for the other. In the crystal, the organic mol­ecules form a dimer, linked by a pair of N—H⋯O hydrogen bonds. The hydroxy groups of the organic mol­ecules donate O—H⋯O hydrogen bonds to water mol­ecules. Further, the hy­droxy group accepts N—H⋯O hydrogen bonds from amides whereas the water mol­ecules donate O—H⋯O hydrogen bonds to the both the amide and ester carbonyl groups. Other weak inter­actions, including C—H⋯O, C—H⋯π and π–π, further consolidate the packing, generating a three-dimensional network.

No MeSH data available.


Three-dimensional crystal structure of the title compound showing the role of the water mol­ecules in the hydrogen-bonding network.
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fig3: Three-dimensional crystal structure of the title compound showing the role of the water mol­ecules in the hydrogen-bonding network.

Mentions: In the crystal of (I), the DHPM mol­ecules form dimers through N—H⋯O hydrogen bonds with an (8) graph-set motif (Fig. 2 ▸). The hy­droxy groups of the di­hydro­pyrimidine mol­ecules donate O—H⋯O hydrogen bonds to water mol­ecules, which may explain the preference for the monohydrated crystalline form. Further, the hy­droxy group accepts N—H⋯O hydrogen bonds from amide groups whereas the water mol­ecule donates O—H⋯O hydrogen bonds to the both the amide and ester carbonyl groups (Table 1 ▸). The key role of the water mol­ecule in the hydrogen-bonding network is shown in Fig. 3 ▸.


Crystal structure of methyl 4-(4-hy ­ droxy ­ phen ­ yl)-6-methyl-2-oxo-1,2,3,4-tetra ­ hydro ­ pyrimidine-5-carboxyl ­ ate monohydrate
Three-dimensional crystal structure of the title compound showing the role of the water mol­ecules in the hydrogen-bonding network.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC5120719&req=5

fig3: Three-dimensional crystal structure of the title compound showing the role of the water mol­ecules in the hydrogen-bonding network.
Mentions: In the crystal of (I), the DHPM mol­ecules form dimers through N—H⋯O hydrogen bonds with an (8) graph-set motif (Fig. 2 ▸). The hy­droxy groups of the di­hydro­pyrimidine mol­ecules donate O—H⋯O hydrogen bonds to water mol­ecules, which may explain the preference for the monohydrated crystalline form. Further, the hy­droxy group accepts N—H⋯O hydrogen bonds from amide groups whereas the water mol­ecule donates O—H⋯O hydrogen bonds to the both the amide and ester carbonyl groups (Table 1 ▸). The key role of the water mol­ecule in the hydrogen-bonding network is shown in Fig. 3 ▸.

View Article: PubMed Central - HTML - PubMed

ABSTRACT

The title hydrate, C13H14N2O4·H2O, crystallizes with two formula units in the asymmetric unit (Z′ = 2). The dihedral angles between the planes of the tetra­hydro­pyrimidine ring and the 4-hy­droxy­phenyl ring and ester group are 86.78 (4) and 6.81 (6)°, respectively, for one mol­ecule and 89.35 (4) and 3.02 (4)° for the other. In the crystal, the organic mol­ecules form a dimer, linked by a pair of N—H⋯O hydrogen bonds. The hydroxy groups of the organic mol­ecules donate O—H⋯O hydrogen bonds to water mol­ecules. Further, the hy­droxy group accepts N—H⋯O hydrogen bonds from amides whereas the water mol­ecules donate O—H⋯O hydrogen bonds to the both the amide and ester carbonyl groups. Other weak inter­actions, including C—H⋯O, C—H⋯π and π–π, further consolidate the packing, generating a three-dimensional network.

No MeSH data available.