Limits...
Crystal structure of 5-hy-droxy-5-propyl-barbituric acid.

Gelbrich T, Griesser UJ - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: This framework has the topology of the 5-connected nov net.Each mol-ecule is linked to five other mol-ecules via six hydrogen bonds, and the descriptor of the hydrogen-bonded structure is F65[4(4).6(6)-nov].The crystal packing is isostructural with that of the previously reported 5-hy-droxy-5-ethyl analogue.

View Article: PubMed Central - HTML - PubMed

Affiliation: University of Innsbruck, Institute of Pharmacy, Innrain 52, 6020 Innsbruck, Austria.

ABSTRACT
Mol-ecules of the title compound, C7H10N2O4, systematic name 5-hy-droxy-5-propyl-pyrimidine-2,4,6(1H,3H,5H)-trione, form a hydrogen-bonded framework which is based on three independent hydrogen bonds, N-H⋯O(carbon-yl), N-H⋯O(hy-droxy) and O-H⋯O(carbon-yl). This framework has the topology of the 5-connected nov net. Each mol-ecule is linked to five other mol-ecules via six hydrogen bonds, and the descriptor of the hydrogen-bonded structure is F65[4(4).6(6)-nov]. The crystal packing is isostructural with that of the previously reported 5-hy-droxy-5-ethyl analogue.

No MeSH data available.


Asymmetric unit with displacement ellipsoids drawn at the 50% probability level and hydrogen atoms drawn as spheres of arbitrary size.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC4645085&req=5

fig1: Asymmetric unit with displacement ellipsoids drawn at the 50% probability level and hydrogen atoms drawn as spheres of arbitrary size.

Mentions: The mol­ecule of the title compound (Fig. 1 ▸) displays a pyrim­idine ring (N1/C2/N3/C4/C5/C6) in a C5-envelope conformation. The ring puckering parameters calculated with PLATON (Spek, 2009 ▸) are θ = 134.4 (3), Φ = 52.2 (5)° and Q = 0.2420 (14) Å. The distance of C5 from the mean plane defined by the other four ring atoms [maximum deviation: N3; −0.033 (1) Å] is −0.342 (2) Å. At ring atom C5 the propyl substituent adopts a trans conformation, and the corresponding torsion angle C5—C8—C9—C10 is −164.80 (13)°. The C5—C8—C9—C10 fragment is twisted significantly out of the plane defined by atoms C8, C5 and C2, which bis­ects the pyrimidine­trione fragment into two approximately sym­met­rical halves, resulting in a pseudo-torsion angle C2⋯C5—C8—C9 of −125.69 (11)°. Closer inspection suggests that this particular geometry may help to prevent unfavourably close intra­molecular contacts between the O7 hy­droxy group and the CH2 group at C9, and may be also facilitate the participation of the hy­droxy group in complex inter­molecular hydrogen-bonding inter­actions.


Crystal structure of 5-hy-droxy-5-propyl-barbituric acid.

Gelbrich T, Griesser UJ - Acta Crystallogr E Crystallogr Commun (2015)

Asymmetric unit with displacement ellipsoids drawn at the 50% probability level and hydrogen atoms drawn as spheres of arbitrary size.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645085&req=5

fig1: Asymmetric unit with displacement ellipsoids drawn at the 50% probability level and hydrogen atoms drawn as spheres of arbitrary size.
Mentions: The mol­ecule of the title compound (Fig. 1 ▸) displays a pyrim­idine ring (N1/C2/N3/C4/C5/C6) in a C5-envelope conformation. The ring puckering parameters calculated with PLATON (Spek, 2009 ▸) are θ = 134.4 (3), Φ = 52.2 (5)° and Q = 0.2420 (14) Å. The distance of C5 from the mean plane defined by the other four ring atoms [maximum deviation: N3; −0.033 (1) Å] is −0.342 (2) Å. At ring atom C5 the propyl substituent adopts a trans conformation, and the corresponding torsion angle C5—C8—C9—C10 is −164.80 (13)°. The C5—C8—C9—C10 fragment is twisted significantly out of the plane defined by atoms C8, C5 and C2, which bis­ects the pyrimidine­trione fragment into two approximately sym­met­rical halves, resulting in a pseudo-torsion angle C2⋯C5—C8—C9 of −125.69 (11)°. Closer inspection suggests that this particular geometry may help to prevent unfavourably close intra­molecular contacts between the O7 hy­droxy group and the CH2 group at C9, and may be also facilitate the participation of the hy­droxy group in complex inter­molecular hydrogen-bonding inter­actions.

Bottom Line: This framework has the topology of the 5-connected nov net.Each mol-ecule is linked to five other mol-ecules via six hydrogen bonds, and the descriptor of the hydrogen-bonded structure is F65[4(4).6(6)-nov].The crystal packing is isostructural with that of the previously reported 5-hy-droxy-5-ethyl analogue.

View Article: PubMed Central - HTML - PubMed

Affiliation: University of Innsbruck, Institute of Pharmacy, Innrain 52, 6020 Innsbruck, Austria.

ABSTRACT
Mol-ecules of the title compound, C7H10N2O4, systematic name 5-hy-droxy-5-propyl-pyrimidine-2,4,6(1H,3H,5H)-trione, form a hydrogen-bonded framework which is based on three independent hydrogen bonds, N-H⋯O(carbon-yl), N-H⋯O(hy-droxy) and O-H⋯O(carbon-yl). This framework has the topology of the 5-connected nov net. Each mol-ecule is linked to five other mol-ecules via six hydrogen bonds, and the descriptor of the hydrogen-bonded structure is F65[4(4).6(6)-nov]. The crystal packing is isostructural with that of the previously reported 5-hy-droxy-5-ethyl analogue.

No MeSH data available.