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

Wang, X.-H.; Hao, W.-J.; Tu, S.-J.

doi:10.1107/S1600536809001391

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 3| March 2009| Page o488

doi:10.1107/S1600536809001391

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

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

^aSchool of Chemistry and Chemical Engineering, Xuzhou Normal University, Xuzhou 221116, People's Republic of China
^*Correspondence e-mail: laotu2001@263.net

(Received 11 January 2009; accepted 12 January 2009; online 6 February 2009)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.041
wR(F²) = 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

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
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

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

Crystal data top

C₁₉H₂₃N₃O₃	F(000) = 728
M_r = 341.40	D_x = 1.220 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 547–549 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.6798 (10) Å	Cell parameters from 2142 reflections
b = 14.8279 (16) Å	θ = 2.4–25.3°
c = 11.8422 (12) Å	µ = 0.08 mm⁻¹
β = 115.022 (2)°	T = 298 K
V = 1858.4 (3) Å³	Block, colorless
Z = 4	0.40 × 0.38 × 0.23 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3262 independent reflections
Radiation source: fine-focus sealed tube	1965 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −13→13
T_min = 0.967, T_max = 0.981	k = −17→9
9104 measured reflections	l = −14→14

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0557P)² + 0.3901P] where P = (F_o² + 2F_c²)/3
3262 reflections	(Δ/σ)_max = 0.001
281 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₉H₂₃N₃O₃	V = 1858.4 (3) Å³
M_r = 341.40	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.6798 (10) Å	µ = 0.08 mm⁻¹
b = 14.8279 (16) Å	T = 298 K
c = 11.8422 (12) Å	0.40 × 0.38 × 0.23 mm
β = 115.022 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3262 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1965 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.981	R_int = 0.034
9104 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	Δρ_max = 0.17 e Å⁻³
3262 reflections	Δρ_min = −0.21 e Å⁻³
281 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.51033 (15)	0.18524 (10)	0.24325 (14)	0.0478 (4)
O2	0.58111 (16)	0.48802 (10)	0.17050 (14)	0.0519 (5)
H2	0.5650	0.5192	0.1084	0.078*
O3	0.36199 (16)	0.38438 (11)	0.37082 (15)	0.0565 (5)
N1	0.45054 (17)	0.24273 (12)	0.04951 (16)	0.0415 (5)
H1	0.4223	0.1907	0.0181	0.050*
N2	0.47888 (17)	0.39142 (12)	0.00944 (16)	0.0407 (5)
N3	0.36553 (17)	0.50839 (13)	0.26475 (16)	0.0436 (5)
H3	0.4105	0.5496	0.2520	0.052*
C1	0.5061 (2)	0.25152 (15)	0.1789 (2)	0.0366 (5)
C2	0.5537 (2)	0.33982 (14)	0.22258 (19)	0.0348 (5)
C3	0.5389 (2)	0.40604 (15)	0.13651 (19)	0.0369 (5)
C4	0.4392 (2)	0.31040 (16)	−0.0272 (2)	0.0430 (6)
H4	0.4004	0.2992	−0.1125	0.052*
C5	0.4234 (2)	0.44262 (15)	0.3448 (2)	0.0414 (6)
C6	0.5653 (2)	0.44127 (15)	0.4011 (2)	0.0433 (6)
H6A	0.5977	0.4429	0.4912	0.052*
H6B	0.5957	0.4945	0.3746	0.052*
C7	0.6153 (2)	0.35575 (14)	0.36151 (19)	0.0385 (5)
H7	0.5905	0.3047	0.3988	0.046*
C8	0.7589 (2)	0.35570 (16)	0.4198 (2)	0.0493 (6)
C9	0.822 (3)	0.3612 (18)	0.342 (3)	0.059 (4)	0.51 (3)
H9	0.7759	0.3626	0.2559	0.071*	0.51 (3)
C9'	0.838 (3)	0.382 (2)	0.370 (3)	0.069 (5)	0.49 (3)
H9'	0.8043	0.4040	0.2884	0.082*	0.49 (3)
C10	0.952 (3)	0.3646 (19)	0.392 (3)	0.074 (4)	0.51 (3)
H10	0.9918	0.3698	0.3383	0.089*	0.51 (3)
C10'	0.970 (3)	0.377 (2)	0.437 (2)	0.083 (6)	0.49 (3)
H10'	1.0222	0.3923	0.3991	0.100*	0.49 (3)
C11	1.025 (4)	0.361 (2)	0.517 (3)	0.072 (6)	0.51 (3)
C11'	1.023 (4)	0.350 (3)	0.561 (3)	0.080 (8)	0.49 (3)
C12	0.964 (2)	0.3535 (19)	0.596 (2)	0.082 (5)	0.51 (3)
H12	1.0112	0.3506	0.6818	0.098*	0.51 (3)
C12'	0.943 (3)	0.3240 (16)	0.611 (2)	0.084 (5)	0.49 (3)
H12'	0.9764	0.3037	0.6925	0.101*	0.49 (3)
C13	0.833 (4)	0.351 (2)	0.545 (4)	0.070 (6)	0.51 (3)
H13	0.7942	0.3453	0.5991	0.084*	0.51 (3)
C13'	0.813 (4)	0.327 (2)	0.544 (4)	0.070 (5)	0.49 (3)
H13'	0.7611	0.3088	0.5821	0.084*	0.49 (3)
C14	1.1676 (18)	0.3628 (15)	0.573 (2)	0.110 (5)	0.51 (3)
H14A	1.1995	0.3023	0.5824	0.164*	0.51 (3)
H14B	1.1991	0.3914	0.6534	0.164*	0.51 (3)
H14C	1.1948	0.3960	0.5194	0.164*	0.51 (3)
C14'	1.1691 (19)	0.3465 (18)	0.635 (2)	0.121 (7)	0.49 (3)
H14D	1.1905	0.3341	0.7209	0.181*	0.49 (3)
H14E	1.2045	0.4035	0.6277	0.181*	0.49 (3)
H14F	1.2024	0.2998	0.6011	0.181*	0.49 (3)
C15	0.2281 (2)	0.51310 (17)	0.1977 (2)	0.0539 (7)
H15	0.1881	0.5034	0.2546	0.065*
C16	0.1793 (3)	0.4455 (2)	0.0910 (3)	0.0839 (10)
H16A	0.2334	0.3927	0.1108	0.101*
H16B	0.0941	0.4264	0.0743	0.101*
C17	0.1810 (3)	0.4946 (3)	−0.0198 (3)	0.1004 (12)
H17A	0.2484	0.4714	−0.0390	0.121*
H17B	0.1014	0.4860	−0.0921	0.121*
C18	0.2015 (3)	0.5919 (3)	0.0119 (3)	0.0961 (12)
H18A	0.1392	0.6282	−0.0534	0.115*
H18B	0.2851	0.6103	0.0221	0.115*
C19	0.1885 (3)	0.60299 (19)	0.1318 (3)	0.0689 (8)
H19A	0.1018	0.6169	0.1158	0.083*
H19B	0.2428	0.6510	0.1816	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0550 (12)	0.0301 (10)	0.0396 (11)	−0.0049 (9)	0.0201 (9)	−0.0058 (9)
N2	0.0532 (12)	0.0373 (11)	0.0322 (10)	−0.0031 (9)	0.0187 (9)	−0.0019 (8)
N3	0.0434 (12)	0.0401 (11)	0.0451 (11)	0.0029 (9)	0.0167 (9)	0.0092 (9)
O1	0.0608 (11)	0.0341 (9)	0.0479 (10)	0.0002 (8)	0.0222 (8)	0.0041 (7)
O2	0.0760 (12)	0.0353 (9)	0.0387 (9)	−0.0096 (8)	0.0189 (8)	0.0005 (7)
O3	0.0634 (12)	0.0471 (10)	0.0624 (11)	0.0063 (9)	0.0300 (9)	0.0180 (9)
C1	0.0384 (13)	0.0360 (13)	0.0370 (13)	0.0040 (10)	0.0176 (10)	−0.0014 (10)
C2	0.0396 (13)	0.0326 (12)	0.0320 (12)	0.0015 (10)	0.0150 (10)	−0.0005 (10)
C3	0.0435 (13)	0.0342 (13)	0.0324 (13)	−0.0015 (10)	0.0155 (11)	−0.0039 (10)
C4	0.0534 (15)	0.0426 (15)	0.0342 (13)	−0.0021 (12)	0.0196 (11)	−0.0062 (11)
C5	0.0538 (15)	0.0362 (13)	0.0349 (13)	0.0062 (12)	0.0195 (11)	−0.0003 (11)
C6	0.0509 (15)	0.0420 (14)	0.0310 (12)	0.0038 (11)	0.0114 (11)	−0.0028 (10)
C7	0.0445 (14)	0.0340 (12)	0.0323 (12)	0.0025 (10)	0.0116 (10)	0.0012 (10)
C8	0.0484 (15)	0.0392 (14)	0.0495 (16)	0.0021 (12)	0.0102 (13)	−0.0047 (12)
C9	0.041 (8)	0.064 (9)	0.064 (9)	−0.007 (6)	0.014 (7)	−0.012 (6)
C9'	0.049 (7)	0.076 (14)	0.062 (11)	−0.009 (9)	0.007 (8)	0.001 (7)
C10	0.047 (9)	0.092 (9)	0.070 (13)	−0.004 (6)	0.013 (10)	−0.010 (8)
C10'	0.047 (10)	0.108 (12)	0.074 (19)	−0.011 (7)	0.006 (12)	−0.012 (11)
C11	0.050 (8)	0.084 (9)	0.067 (18)	−0.003 (6)	0.009 (12)	0.005 (13)
C11'	0.054 (10)	0.090 (13)	0.071 (18)	0.006 (10)	0.003 (12)	−0.003 (12)
C12	0.054 (10)	0.097 (14)	0.068 (9)	−0.011 (10)	0.000 (7)	−0.004 (8)
C12'	0.058 (10)	0.081 (11)	0.078 (7)	−0.006 (7)	−0.007 (6)	0.014 (7)
C13	0.054 (12)	0.078 (15)	0.057 (6)	−0.006 (9)	0.003 (7)	−0.004 (10)
C13'	0.054 (12)	0.078 (15)	0.058 (6)	−0.006 (9)	0.003 (7)	−0.003 (10)
C14	0.056 (5)	0.126 (9)	0.106 (13)	0.000 (5)	−0.005 (9)	0.007 (10)
C14'	0.054 (5)	0.150 (14)	0.112 (13)	0.000 (7)	−0.010 (10)	−0.010 (12)
C15	0.0443 (15)	0.0508 (16)	0.0633 (17)	0.0038 (12)	0.0195 (13)	0.0137 (13)
C16	0.0547 (19)	0.068 (2)	0.097 (3)	−0.0028 (16)	0.0014 (17)	−0.0018 (19)
C17	0.084 (3)	0.133 (4)	0.082 (3)	0.023 (2)	0.033 (2)	−0.003 (2)
C18	0.077 (2)	0.119 (3)	0.078 (2)	−0.004 (2)	0.0194 (19)	0.036 (2)
C19	0.0533 (17)	0.0587 (18)	0.083 (2)	0.0101 (14)	0.0174 (15)	0.0209 (16)

Geometric parameters (Å, º) top

O1—C1	1.232 (2)	C12—C13	1.39 (5)
O2—C3	1.310 (2)	C12—H12	0.9300
O2—H2	0.8200	C13—H13	0.9300
O3—C5	1.242 (3)	C14—H14A	0.9600
N1—C4	1.322 (3)	C14—H14B	0.9600
N1—C1	1.395 (3)	C14—H14C	0.9600
N1—H1	0.8600	C9'—C10'	1.41 (5)
N2—C4	1.295 (3)	C9'—H9'	0.9300
N2—C3	1.382 (3)	C10'—C11'	1.38 (3)
N3—C5	1.328 (3)	C10'—H10'	0.9300
N3—C15	1.460 (3)	C11'—C12'	1.35 (4)
N3—H3	0.8600	C11'—C14'	1.56 (4)
C1—C2	1.431 (3)	C12'—C13'	1.38 (6)
C2—C3	1.373 (3)	C12'—H12'	0.9300
C2—C7	1.510 (3)	C13'—H13'	0.9300
C4—H4	0.9300	C14'—H14D	0.9600
C5—C6	1.503 (3)	C14'—H14E	0.9600
C6—C7	1.549 (3)	C14'—H14F	0.9600
C6—H6A	0.9700	C15—C19	1.515 (3)
C6—H6B	0.9700	C15—C16	1.523 (4)
C7—C8	1.520 (3)	C15—H15	0.9800
C7—H7	0.9800	C16—C17	1.509 (5)
C8—C9'	1.35 (4)	C16—H16A	0.9700
C8—C13	1.37 (4)	C16—H16B	0.9700
C8—C13'	1.40 (4)	C17—C18	1.485 (5)
C8—C9	1.41 (3)	C17—H17A	0.9700
C9—C10	1.38 (5)	C17—H17B	0.9700
C9—H9	0.9300	C18—C19	1.500 (4)
C10—C11	1.37 (3)	C18—H18A	0.9700
C10—H10	0.9300	C18—H18B	0.9700
C11—C12	1.39 (4)	C19—H19A	0.9700
C11—C14	1.51 (4)	C19—H19B	0.9700

C3—O2—H2	109.5	C11—C14—H14A	109.5
C4—N1—C1	123.31 (19)	C11—C14—H14B	109.5
C4—N1—H1	118.3	H14A—C14—H14B	109.5
C1—N1—H1	118.3	C11—C14—H14C	109.5
C4—N2—C3	117.10 (19)	H14A—C14—H14C	109.5
C5—N3—C15	122.2 (2)	H14B—C14—H14C	109.5
C5—N3—H3	118.9	C8—C9'—C10'	121 (3)
C15—N3—H3	118.9	C8—C9'—H9'	119.3
O1—C1—N1	118.9 (2)	C10'—C9'—H9'	119.3
O1—C1—C2	126.8 (2)	C11'—C10'—C9'	121 (3)
N1—C1—C2	114.31 (19)	C11'—C10'—H10'	119.7
C3—C2—C1	118.59 (19)	C9'—C10'—H10'	119.7
C3—C2—C7	123.34 (18)	C12'—C11'—C10'	118 (3)
C1—C2—C7	118.06 (18)	C12'—C11'—C14'	123 (2)
O2—C3—C2	121.54 (19)	C10'—C11'—C14'	120 (2)
O2—C3—N2	115.58 (18)	C11'—C12'—C13'	123 (3)
C2—C3—N2	122.88 (19)	C11'—C12'—H12'	118.7
N2—C4—N1	123.8 (2)	C13'—C12'—H12'	118.7
N2—C4—H4	118.1	C12'—C13'—C8	120 (3)
N1—C4—H4	118.1	C12'—C13'—H13'	119.9
O3—C5—N3	121.0 (2)	C8—C13'—H13'	119.9
O3—C5—C6	121.7 (2)	C11'—C14'—H14D	109.5
N3—C5—C6	117.3 (2)	C11'—C14'—H14E	109.5
C5—C6—C7	111.29 (18)	H14D—C14'—H14E	109.5
C5—C6—H6A	109.4	C11'—C14'—H14F	109.5
C7—C6—H6A	109.4	H14D—C14'—H14F	109.5
C5—C6—H6B	109.4	H14E—C14'—H14F	109.5
C7—C6—H6B	109.4	N3—C15—C19	110.4 (2)
H6A—C6—H6B	108.0	N3—C15—C16	111.1 (2)
C2—C7—C8	114.88 (19)	C19—C15—C16	103.1 (2)
C2—C7—C6	112.99 (17)	N3—C15—H15	110.7
C8—C7—C6	110.36 (18)	C19—C15—H15	110.7
C2—C7—H7	105.9	C16—C15—H15	110.7
C8—C7—H7	105.9	C17—C16—C15	105.4 (3)
C6—C7—H7	105.9	C17—C16—H16A	110.7
C9'—C8—C13	104.8 (18)	C15—C16—H16A	110.7
C9'—C8—C13'	118 (2)	C17—C16—H16B	110.7
C13—C8—C9	116 (2)	C15—C16—H16B	110.7
C13'—C8—C9	125 (2)	H16A—C16—H16B	108.8
C9'—C8—C7	129.0 (14)	C18—C17—C16	108.0 (3)
C13—C8—C7	124.3 (17)	C18—C17—H17A	110.1
C13'—C8—C7	113.3 (17)	C16—C17—H17A	110.1
C9—C8—C7	119.2 (12)	C18—C17—H17B	110.1
C10—C9—C8	121 (2)	C16—C17—H17B	110.1
C10—C9—H9	119.6	H17A—C17—H17B	108.4
C8—C9—H9	119.6	C17—C18—C19	106.0 (3)
C11—C10—C9	122 (3)	C17—C18—H18A	110.5
C11—C10—H10	119.0	C19—C18—H18A	110.5
C9—C10—H10	119.0	C17—C18—H18B	110.5
C10—C11—C12	118 (3)	C19—C18—H18B	110.5
C10—C11—C14	123 (3)	H18A—C18—H18B	108.7
C12—C11—C14	119 (2)	C18—C19—C15	105.1 (3)
C13—C12—C11	120 (3)	C18—C19—H19A	110.7
C13—C12—H12	120.1	C15—C19—H19A	110.7
C11—C12—H12	120.1	C18—C19—H19B	110.7
C8—C13—C12	123 (3)	C15—C19—H19B	110.7
C8—C13—H13	118.5	H19A—C19—H19B	108.8
C12—C13—H13	118.5

C4—N1—C1—O1	178.5 (2)	C7—C8—C9—C10	177.6 (19)
C4—N1—C1—C2	−1.8 (3)	C8—C9—C10—C11	2 (4)
O1—C1—C2—C3	−179.2 (2)	C9—C10—C11—C12	0 (5)
N1—C1—C2—C3	1.2 (3)	C9—C10—C11—C14	179 (3)
O1—C1—C2—C7	−0.4 (3)	C10—C11—C12—C13	0 (5)
N1—C1—C2—C7	179.93 (18)	C14—C11—C12—C13	−180 (3)
C1—C2—C3—O2	−179.52 (19)	C9'—C8—C13—C12	−13 (3)
C7—C2—C3—O2	1.8 (3)	C13'—C8—C13—C12	126 (14)
C1—C2—C3—N2	0.7 (3)	C9—C8—C13—C12	2 (4)
C7—C2—C3—N2	−178.0 (2)	C7—C8—C13—C12	−178 (2)
C4—N2—C3—O2	178.1 (2)	C11—C12—C13—C8	−1 (5)
C4—N2—C3—C2	−2.1 (3)	C13—C8—C9'—C10'	16 (3)
C3—N2—C4—N1	1.5 (3)	C13'—C8—C9'—C10'	3 (3)
C1—N1—C4—N2	0.5 (3)	C9—C8—C9'—C10'	−118 (10)
C15—N3—C5—O3	−3.8 (3)	C7—C8—C9'—C10'	−179.8 (17)
C15—N3—C5—C6	175.70 (19)	C8—C9'—C10'—C11'	−4 (5)
O3—C5—C6—C7	63.5 (3)	C9'—C10'—C11'—C12'	4 (5)
N3—C5—C6—C7	−115.9 (2)	C9'—C10'—C11'—C14'	−179 (2)
C3—C2—C7—C8	−80.4 (3)	C10'—C11'—C12'—C13'	−2 (5)
C1—C2—C7—C8	100.9 (2)	C14'—C11'—C12'—C13'	−179 (3)
C3—C2—C7—C6	47.4 (3)	C11'—C12'—C13'—C8	1 (5)
C1—C2—C7—C6	−131.3 (2)	C9'—C8—C13'—C12'	−1 (4)
C5—C6—C7—C2	50.0 (2)	C13—C8—C13'—C12'	−47 (10)
C5—C6—C7—C8	−179.86 (19)	C9—C8—C13'—C12'	18 (4)
C2—C7—C8—C9'	31.9 (16)	C7—C8—C13'—C12'	−179 (2)
C6—C7—C8—C9'	−97.3 (16)	C5—N3—C15—C19	169.8 (2)
C2—C7—C8—C13	−166.3 (17)	C5—N3—C15—C16	−76.5 (3)
C6—C7—C8—C13	64.5 (18)	N3—C15—C16—C17	−89.0 (3)
C2—C7—C8—C13'	−150.5 (16)	C19—C15—C16—C17	29.2 (3)
C6—C7—C8—C13'	80.4 (16)	C15—C16—C17—C18	−12.2 (4)
C2—C7—C8—C9	13.8 (13)	C16—C17—C18—C19	−10.0 (4)
C6—C7—C8—C9	−115.4 (13)	C17—C18—C19—C15	28.6 (3)
C9'—C8—C9—C10	50 (8)	N3—C15—C19—C18	83.0 (3)
C13—C8—C9—C10	−2 (3)	C16—C15—C19—C18	−35.7 (3)
C13'—C8—C9—C10	−20 (3)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₃N₃O₃
M_r	341.40
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.6798 (10), 14.8279 (16), 11.8422 (12)
β (°)	115.022 (2)
V (Å³)	1858.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.38 × 0.23

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.967, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	9104, 3262, 1965
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.130, 1.03
No. of reflections	3262
No. of parameters	281
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.21

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x+1, −y+1, −z; (iii) −x+1, y+1/2, −z+1/2.

Acknowledgements

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

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. CrossRef Web of Science Google Scholar
Bruker (1998). SMART, SAINT and SADABS. Bruker AXS, Inc., Madison, Wisconsin, USA. Google Scholar
Erian, A. W. (1993). Chem. Rev. 93, 1991–2005. CrossRef CAS Web of Science Google Scholar
Janeba, Z., Balzarini, J., Andrei, G., Robert Snoeck, R., De Clercq, E. & Robins, M. J. (2005). J. Med. Chem. 48, 4690–4696. Web of Science CrossRef PubMed CAS Google Scholar
Johar, M., Manning, T., Kunimoto, D. Y. & Kumar, R. (2005). Bioorg. Med. Chem. 13, 6663—6671. Web of Science CrossRef Google Scholar
Lagoja, I. M. (2005). Chem. Biodivers. 2, 1–50. Web of Science CrossRef PubMed CAS Google Scholar
Mathews, A. & Asokan, C. V. (2007). Tetrahedron, 63, 7845–7849. Web of Science CrossRef CAS Google Scholar
Michael, J. P. (2005). Nat. Prod. Rep. 22, 627–646. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soloducho, J., Doskocz, J., Cabaj, J. & Roszak, S. (2003). Tetrahedron, 59, 4761–4766. Web of Science CrossRef CAS Google Scholar

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

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Experimental

Crystal data

Data collection

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organic compounds

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