N-Cyclo­pentyl-3-(4-hydr­oxy-6-oxo-1,6-dihydro­pyrimidin-5-yl)-3-p-tolyl­propanamide

Xing-Han Wang; Wen-Juan Hao; Shu-Jiang Tu

doi:10.1107/S1600536809001391

. 2009 Feb 6;65(Pt 3):o488. doi: 10.1107/S1600536809001391

N-Cyclopentyl-3-(4-hydroxy-6-oxo-1,6-dihydropyrimidin-5-yl)-3-p-tolylpropanamide

Xing-Han Wang ^a, Wen-Juan Hao ^a, Shu-Jiang Tu ^a,^*

PMCID: PMC2968560 PMID: 21582155

Abstract

In the molecule of the title compound, C₁₉H₂₃N₃O₃, the six-membered rings are oriented at a dihedral angle of 73.06 (3)°. The cyclopentyl ring adopts an envelope conformation. In the crystal structure, intermolecular N—H⋯O and O—H⋯N hydrogen bonds link the molecules. In the tolyl ring, the H atoms and all but one of the C atoms are disordered over two positions and were refined with occupancies of 0.51 (3) and 0.49 (3).

Related literature

For general background, see: Johar et al. (2005 ▶); Janeba et al. (2005 ▶); Soloducho et al. (2003 ▶); Mathews & Asokan (2007 ▶); Lagoja (2005 ▶); Michael (2005 ▶); Erian (1993 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₉H₂₃N₃O₃
M _r = 341.40
Monoclinic,
a = 11.6798 (10) Å
b = 14.8279 (16) Å
c = 11.8422 (12) Å
β = 115.022 (2)°
V = 1858.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 (2) K
0.40 × 0.38 × 0.23 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.967, T _max = 0.981
9104 measured reflections
3262 independent reflections
1965 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.130
S = 1.03
3262 reflections
281 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; 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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001391/hk2612sup1.cif

e-65-0o488-sup1.cif^{(23.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001391/hk2612Isup2.hkl

e-65-0o488-Isup2.hkl^{(160KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	1.93	2.692 (3)	147
O2—H2⋯N2ⁱⁱ	0.82	1.83	2.639 (3)	167
N3—H3⋯O1ⁱⁱⁱ	0.86	2.20	3.017 (3)	158

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

We thank the Natural Science Foundation of China (grant No. 20672090) and the Natural Science Foundation of Jiangsu Province (grant No. BK2006033).

supplementary crystallographic information

Comment

The pyrimidines and their derivatives as a class of extremely important heterocyclic compounds are used in a wide array of synthetic and industrial applications. Not only they are an integral part of the genetic materials, viz. DNA and RNA as nucleotides and nucleosides but also play critical roles especially in pharmaceutical fields (Johar et al., 2005; Janeba et al., 2005). Some pyrimidine derivatives can give stable and good quality nanomaterials having many important electrical and optical properties (Soloducho et al., 2003; Mathews & Asokan, 2007), and also used as functional materials (Lagoja, 2005; Michael, 2005; Erian, 1993). We report herein the crystal structure of the title compound.

In the molecule of the title compound (Fig 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. Rings A (N1/N2/C1-C4) and B (C8-C13) are, of course, planar, and they are oriented at a dihedral angle of 73.06 (3)°. The five-membered ring C (C15-C19) adopts envelope conformation with C15 atom displaced by -0.511 (3) Å from the plane of the other ring atoms.

In the crystal structure, intermolecular N-H···O and O-H···N hydrogen bonds (Table 1) link the molecules, in which they may be effective in the stabilization of the structure.

Experimental

The title compound was prepared by the reaction of p-tolylidene-Meldrum's acid (1 mmol) with 6-hydroxypyrimidin-4(3H)-one (1 mmol) and cyclopentanamine (1 mmol) at 373 K in glacial acetic acid under microwave irradiation (maximum power 250 W, initial power 100 W) for 20 min (yield; 87%, m.p. 547–549 K). Crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation.