N-Cyclo­hexyl-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/S1600536809001251

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o309

doi:10.1107/S1600536809001251

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N-Cyclohexyl-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 4 January 2009; accepted 11 January 2009; online 14 January 2009)

In the molecule of the title compound, C₂₀H₂₅N₃O₃, the aromatic rings are oriented at a dihedral angle of 88.36 (3)°. The cyclohexane ring adopts a chair conformation. In the crystal structure, intermolecular N—H⋯O and O—H⋯N hydrogen bonds link the molecules. C—H⋯π interactions are also present.

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 ). For ring-puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₀H₂₅N₃O₃
M_r = 355.43
Monoclinic, P 2₁ /n
a = 7.1563 (12) Å
b = 19.637 (2) Å
c = 13.2746 (18) Å
β = 101.740 (2)°
V = 1826.5 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.23 × 0.16 × 0.14 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.980, T_max = 0.988
9491 measured reflections
3216 independent reflections
1916 reflections with I > 2σ(I)
R_int = 0.073

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.104
S = 1.02
3216 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 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	1.98	2.813 (3)	162
O1—H1A⋯N2ⁱⁱ	0.82	1.95	2.753 (3)	168
N3—H3⋯O2ⁱⁱⁱ	0.86	2.19	2.992 (4)	155
C17—H17B⋯Cg2^iv	0.97	2.47	3.440 (3)	177
C20—H20A⋯Cg2^v	0.97	2.74	3.629 (3)	152
Symmetry codes: (i) x+1, y, z; (ii) -x+2, -y+2, -z+2; (iii) -x+2, -y+2, -z+1; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) -x, -y, -z+1. Cg2 is centroid of the C8–C13 ring.

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 (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001251/hk2610sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809001251/hk2610Isup2.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 88.36 (3)°. The cyclohexane ring C (C15-C20), having total puckering amplitude, Q_T, of 0.565 (3) Å, chair conformation [ϕ = -30.33 (3)° and θ = 4.00 (3)°] (Cremer & Pople, 1975).

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. There also exist C–H···π interactions (Table 1).

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). For ring-puckering parameters, see: Cremer & Pople (1975). Cg2 is centroid of the C8–C13 ring.

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 cyclohexanamine (1 mmol) at 373 K in glacial acetic acid under microwave irradiation (maximum power 250 W, initial power 100 W) for 18 min (yield; 83%, m.p. 534–536 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 (Bruker, 1998); software used to prepare material for publication: SHELXTL (Bruker, 1998).

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

Crystal data top

C₂₀H₂₅N₃O₃	F(000) = 760
M_r = 355.43	D_x = 1.293 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 534–536 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.1563 (12) Å	Cell parameters from 1921 reflections
b = 19.637 (2) Å	θ = 2.6–27.7°
c = 13.2746 (18) Å	µ = 0.09 mm⁻¹
β = 101.740 (2)°	T = 298 K
V = 1826.5 (4) Å³	Block, colorless
Z = 4	0.23 × 0.16 × 0.14 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3216 independent reflections
Radiation source: fine-focus sealed tube	1916 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.073
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→8
T_min = 0.980, T_max = 0.988	k = −23→21
9491 measured reflections	l = −15→15

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0354P)²] where P = (F_o² + 2F_c²)/3
3216 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₀H₂₅N₃O₃	V = 1826.5 (4) Å³
M_r = 355.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.1563 (12) Å	µ = 0.09 mm⁻¹
b = 19.637 (2) Å	T = 298 K
c = 13.2746 (18) Å	0.23 × 0.16 × 0.14 mm
β = 101.740 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3216 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1916 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.988	R_int = 0.073
9491 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	Δρ_max = 0.16 e Å⁻³
3216 reflections	Δρ_min = −0.19 e Å⁻³
235 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
O1	0.8327 (2)	1.04303 (8)	0.89288 (11)	0.0456 (5)
H1A	0.8598	1.0297	0.9526	0.068*
O2	1.1335 (2)	1.04358 (9)	0.60752 (11)	0.0511 (5)
O3	0.5892 (2)	0.93937 (8)	0.69802 (11)	0.0447 (4)
N1	1.2782 (3)	1.00038 (10)	0.76292 (14)	0.0387 (5)
H1	1.3786	0.9909	0.7394	0.046*
N2	1.1340 (3)	0.99789 (9)	0.90587 (13)	0.0367 (5)
N3	0.7956 (3)	0.91122 (9)	0.59665 (13)	0.0378 (5)
H3	0.8514	0.9251	0.5488	0.045*
C1	1.2753 (3)	0.98462 (12)	0.86043 (17)	0.0396 (6)
H1B	1.3815	0.9626	0.8987	0.048*
C2	0.9778 (3)	1.02944 (11)	0.84599 (16)	0.0316 (5)
C3	0.9650 (3)	1.04690 (10)	0.74467 (15)	0.0290 (5)
C4	1.1234 (3)	1.03189 (11)	0.69730 (17)	0.0346 (6)
C5	0.6857 (3)	0.95565 (11)	0.63376 (16)	0.0329 (6)
C6	0.6872 (3)	1.02749 (11)	0.59477 (16)	0.0350 (6)
H6A	0.5572	1.0422	0.5679	0.042*
H6B	0.7563	1.0291	0.5391	0.042*
C7	0.7820 (3)	1.07626 (11)	0.68124 (15)	0.0317 (6)
H7	0.6931	1.0795	0.7283	0.038*
C8	0.8005 (3)	1.14835 (11)	0.64204 (16)	0.0302 (5)
C9	0.6815 (3)	1.17248 (12)	0.55327 (17)	0.0366 (6)
H9	0.6022	1.1421	0.5108	0.044*
C10	0.6781 (3)	1.24068 (12)	0.52658 (18)	0.0400 (6)
H10	0.5952	1.2553	0.4672	0.048*
C11	0.7955 (4)	1.28759 (12)	0.58638 (19)	0.0393 (6)
C12	0.9218 (4)	1.26311 (12)	0.67173 (19)	0.0412 (6)
H12	1.0068	1.2931	0.7115	0.049*
C13	0.9251 (3)	1.19530 (12)	0.69940 (17)	0.0367 (6)
H13	1.0118	1.1806	0.7573	0.044*
C14	0.7807 (4)	1.36269 (12)	0.5595 (2)	0.0587 (8)
H14A	0.8643	1.3731	0.5135	0.088*
H14B	0.8168	1.3892	0.6212	0.088*
H14C	0.6517	1.3734	0.5269	0.088*
C15	0.8280 (3)	0.84081 (11)	0.63122 (17)	0.0367 (6)
H15	0.7200	0.8266	0.6614	0.044*
C16	1.0092 (4)	0.83383 (13)	0.71338 (18)	0.0488 (7)
H16A	0.9999	0.8627	0.7714	0.059*
H16B	1.1174	0.8492	0.6857	0.059*
C17	1.0429 (4)	0.76056 (13)	0.75025 (19)	0.0532 (7)
H17A	1.1649	0.7576	0.7979	0.064*
H17B	0.9442	0.7473	0.7868	0.064*
C18	1.0418 (4)	0.71171 (14)	0.6614 (2)	0.0593 (8)
H18A	1.1538	0.7198	0.6324	0.071*
H18B	1.0483	0.6653	0.6869	0.071*
C19	0.8642 (4)	0.72005 (12)	0.5780 (2)	0.0556 (8)
H19A	0.7536	0.7057	0.6043	0.067*
H19B	0.8738	0.6910	0.5202	0.067*
C20	0.8367 (4)	0.79365 (12)	0.54125 (18)	0.0435 (6)
H20A	0.9418	0.8070	0.5095	0.052*
H20B	0.7195	0.7975	0.4900	0.052*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0413 (10)	0.0669 (13)	0.0301 (9)	0.0186 (9)	0.0109 (8)	0.0084 (8)
O2	0.0557 (12)	0.0680 (13)	0.0339 (10)	0.0139 (10)	0.0193 (9)	0.0113 (8)
O3	0.0467 (11)	0.0426 (10)	0.0503 (10)	0.0067 (8)	0.0227 (9)	0.0080 (8)
N1	0.0312 (12)	0.0497 (13)	0.0373 (11)	0.0088 (10)	0.0120 (10)	0.0044 (10)
N2	0.0357 (12)	0.0444 (13)	0.0295 (11)	0.0122 (10)	0.0057 (9)	0.0041 (9)
N3	0.0432 (13)	0.0354 (12)	0.0390 (11)	0.0032 (10)	0.0185 (10)	0.0063 (9)
C1	0.0356 (15)	0.0456 (15)	0.0353 (14)	0.0085 (12)	0.0020 (12)	0.0041 (11)
C2	0.0292 (13)	0.0365 (14)	0.0286 (13)	0.0043 (11)	0.0047 (11)	−0.0004 (10)
C3	0.0301 (13)	0.0301 (13)	0.0257 (12)	0.0031 (11)	0.0030 (10)	0.0007 (10)
C4	0.0371 (15)	0.0360 (14)	0.0304 (13)	0.0042 (12)	0.0061 (12)	0.0026 (11)
C5	0.0296 (14)	0.0373 (15)	0.0302 (13)	−0.0008 (11)	0.0024 (11)	0.0011 (11)
C6	0.0363 (15)	0.0344 (14)	0.0319 (13)	0.0028 (11)	0.0016 (11)	0.0038 (10)
C7	0.0340 (14)	0.0347 (14)	0.0263 (12)	0.0042 (11)	0.0059 (11)	0.0018 (10)
C8	0.0277 (13)	0.0324 (14)	0.0305 (13)	0.0052 (11)	0.0063 (11)	0.0021 (11)
C9	0.0315 (14)	0.0359 (15)	0.0403 (14)	−0.0024 (11)	0.0020 (12)	0.0036 (11)
C10	0.0372 (15)	0.0397 (15)	0.0420 (15)	0.0012 (13)	0.0053 (12)	0.0081 (12)
C11	0.0348 (15)	0.0356 (15)	0.0493 (16)	0.0008 (12)	0.0130 (13)	0.0031 (12)
C12	0.0328 (15)	0.0378 (15)	0.0537 (17)	−0.0081 (12)	0.0104 (13)	−0.0084 (12)
C13	0.0292 (14)	0.0418 (15)	0.0376 (14)	0.0014 (12)	0.0034 (12)	−0.0012 (11)
C14	0.066 (2)	0.0381 (17)	0.0760 (19)	0.0006 (14)	0.0241 (16)	0.0061 (14)
C15	0.0355 (15)	0.0356 (15)	0.0413 (14)	0.0049 (11)	0.0132 (12)	0.0074 (11)
C16	0.0460 (17)	0.0539 (17)	0.0462 (16)	0.0012 (14)	0.0090 (14)	0.0077 (13)
C17	0.0423 (17)	0.0642 (19)	0.0551 (17)	0.0101 (14)	0.0148 (14)	0.0224 (15)
C18	0.0567 (19)	0.0523 (19)	0.075 (2)	0.0196 (15)	0.0281 (17)	0.0207 (15)
C19	0.059 (2)	0.0414 (17)	0.071 (2)	0.0062 (14)	0.0233 (17)	−0.0026 (14)
C20	0.0406 (16)	0.0427 (16)	0.0477 (15)	0.0063 (13)	0.0099 (13)	−0.0021 (12)

Geometric parameters (Å, º) top

N1—C1	1.335 (3)	C10—H10	0.9300
N1—C4	1.406 (3)	C11—C12	1.384 (3)
N1—H1	0.8600	C11—C14	1.516 (3)
N2—C1	1.305 (3)	C12—C13	1.380 (3)
N2—C2	1.380 (3)	C12—H12	0.9300
N3—C5	1.334 (3)	C13—H13	0.9300
N3—C15	1.460 (3)	C14—H14A	0.9600
N3—H3	0.8600	C14—H14B	0.9600
O1—C2	1.341 (2)	C14—H14C	0.9600
O1—H1A	0.8200	C15—C16	1.522 (3)
O2—C4	1.230 (2)	C15—C20	1.523 (3)
O3—C5	1.244 (2)	C15—H15	0.9800
C1—H1B	0.9300	C16—C17	1.523 (3)
C2—C3	1.373 (3)	C16—H16A	0.9700
C3—C4	1.435 (3)	C16—H16B	0.9700
C3—C7	1.519 (3)	C17—C18	1.519 (4)
C5—C6	1.504 (3)	C17—H17A	0.9700
C6—C7	1.542 (3)	C17—H17B	0.9700
C6—H6A	0.9700	C18—C19	1.515 (4)
C6—H6B	0.9700	C18—H18A	0.9700
C7—C8	1.523 (3)	C18—H18B	0.9700
C7—H7	0.9800	C19—C20	1.525 (3)
C8—C9	1.390 (3)	C19—H19A	0.9700
C8—C13	1.396 (3)	C19—H19B	0.9700
C9—C10	1.384 (3)	C20—H20A	0.9700
C9—H9	0.9300	C20—H20B	0.9700
C10—C11	1.383 (3)

C1—N1—C4	122.5 (2)	C13—C12—H12	119.1
C1—N1—H1	118.8	C11—C12—H12	119.1
C4—N1—H1	118.8	C12—C13—C8	121.2 (2)
C1—N2—C2	115.89 (18)	C12—C13—H13	119.4
C5—N3—C15	124.82 (18)	C8—C13—H13	119.4
C5—N3—H3	117.6	C11—C14—H14A	109.5
C15—N3—H3	117.6	C11—C14—H14B	109.5
C2—O1—H1A	109.5	H14A—C14—H14B	109.5
N2—C1—N1	124.6 (2)	C11—C14—H14C	109.5
N2—C1—H1B	117.7	H14A—C14—H14C	109.5
N1—C1—H1B	117.7	H14B—C14—H14C	109.5
O1—C2—C3	120.1 (2)	N3—C15—C16	111.59 (19)
O1—C2—N2	115.78 (18)	N3—C15—C20	111.02 (18)
C3—C2—N2	124.1 (2)	C16—C15—C20	110.01 (19)
C2—C3—C4	118.5 (2)	N3—C15—H15	108.0
C2—C3—C7	121.06 (19)	C16—C15—H15	108.0
C4—C3—C7	120.26 (18)	C20—C15—H15	108.0
O2—C4—N1	119.2 (2)	C15—C16—C17	111.8 (2)
O2—C4—C3	126.4 (2)	C15—C16—H16A	109.3
N1—C4—C3	114.34 (18)	C17—C16—H16A	109.3
O3—C5—N3	122.4 (2)	C15—C16—H16B	109.3
O3—C5—C6	121.4 (2)	C17—C16—H16B	109.3
N3—C5—C6	116.14 (19)	H16A—C16—H16B	107.9
C5—C6—C7	111.05 (17)	C18—C17—C16	111.8 (2)
C5—C6—H6A	109.4	C18—C17—H17A	109.3
C7—C6—H6A	109.4	C16—C17—H17A	109.3
C5—C6—H6B	109.4	C18—C17—H17B	109.3
C7—C6—H6B	109.4	C16—C17—H17B	109.3
H6A—C6—H6B	108.0	H17A—C17—H17B	107.9
C3—C7—C8	114.65 (18)	C19—C18—C17	111.7 (2)
C3—C7—C6	112.09 (17)	C19—C18—H18A	109.3
C8—C7—C6	112.24 (17)	C17—C18—H18A	109.3
C3—C7—H7	105.7	C19—C18—H18B	109.3
C8—C7—H7	105.7	C17—C18—H18B	109.3
C6—C7—H7	105.7	H18A—C18—H18B	107.9
C9—C8—C13	116.8 (2)	C18—C19—C20	111.7 (2)
C9—C8—C7	121.7 (2)	C18—C19—H19A	109.3
C13—C8—C7	121.2 (2)	C20—C19—H19A	109.3
C10—C9—C8	121.5 (2)	C18—C19—H19B	109.3
C10—C9—H9	119.2	C20—C19—H19B	109.3
C8—C9—H9	119.2	H19A—C19—H19B	107.9
C11—C10—C9	121.4 (2)	C15—C20—C19	110.4 (2)
C11—C10—H10	119.3	C15—C20—H20A	109.6
C9—C10—H10	119.3	C19—C20—H20A	109.6
C10—C11—C12	117.3 (2)	C15—C20—H20B	109.6
C10—C11—C14	120.5 (2)	C19—C20—H20B	109.6
C12—C11—C14	122.2 (2)	H20A—C20—H20B	108.1
C13—C12—C11	121.7 (2)

C2—N2—C1—N1	1.1 (3)	C3—C7—C8—C9	153.35 (19)
C4—N1—C1—N2	−1.8 (4)	C6—C7—C8—C9	24.0 (3)
C1—N2—C2—O1	180.0 (2)	C3—C7—C8—C13	−33.2 (3)
C1—N2—C2—C3	−0.1 (3)	C6—C7—C8—C13	−162.62 (19)
O1—C2—C3—C4	179.7 (2)	C13—C8—C9—C10	−4.0 (3)
N2—C2—C3—C4	−0.3 (3)	C7—C8—C9—C10	169.7 (2)
O1—C2—C3—C7	−5.2 (3)	C8—C9—C10—C11	1.0 (3)
N2—C2—C3—C7	174.9 (2)	C9—C10—C11—C12	2.5 (3)
C1—N1—C4—O2	−178.3 (2)	C9—C10—C11—C14	−176.1 (2)
C1—N1—C4—C3	1.3 (3)	C10—C11—C12—C13	−3.1 (3)
C2—C3—C4—O2	179.2 (2)	C14—C11—C12—C13	175.5 (2)
C7—C3—C4—O2	4.0 (4)	C11—C12—C13—C8	0.1 (3)
C2—C3—C4—N1	−0.3 (3)	C9—C8—C13—C12	3.4 (3)
C7—C3—C4—N1	−175.56 (18)	C7—C8—C13—C12	−170.3 (2)
C15—N3—C5—O3	−4.8 (3)	C5—N3—C15—C16	−94.9 (3)
C15—N3—C5—C6	174.2 (2)	C5—N3—C15—C20	142.0 (2)
O3—C5—C6—C7	66.6 (3)	N3—C15—C16—C17	179.60 (18)
N3—C5—C6—C7	−112.4 (2)	C20—C15—C16—C17	−56.7 (3)
C2—C3—C7—C8	117.4 (2)	C15—C16—C17—C18	54.0 (3)
C4—C3—C7—C8	−67.5 (3)	C16—C17—C18—C19	−52.2 (3)
C2—C3—C7—C6	−113.1 (2)	C17—C18—C19—C20	54.0 (3)
C4—C3—C7—C6	62.0 (3)	N3—C15—C20—C19	−178.2 (2)
C5—C6—C7—C3	44.5 (2)	C16—C15—C20—C19	57.8 (3)
C5—C6—C7—C8	175.24 (18)	C18—C19—C20—C15	−57.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	1.98	2.813 (3)	162
O1—H1A···N2ⁱⁱ	0.82	1.95	2.753 (3)	168
N3—H3···O2ⁱⁱⁱ	0.86	2.19	2.992 (4)	155
C17—H17B···Cg2^iv	0.97	2.47	3.440 (3)	177
C20—H20A···Cg2^v	0.97	2.74	3.629 (3)	152

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

Experimental details

Crystal data
Chemical formula	C₂₀H₂₅N₃O₃
M_r	355.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.1563 (12), 19.637 (2), 13.2746 (18)
β (°)	101.740 (2)
V (Å³)	1826.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.23 × 0.16 × 0.14

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.980, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	9491, 3216, 1916
R_int	0.073
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.104, 1.02
No. of reflections	3216
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.19

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	1.98	2.813 (3)	162
O1—H1A···N2ⁱⁱ	0.82	1.95	2.753 (3)	168
N3—H3···O2ⁱⁱⁱ	0.86	2.19	2.992 (4)	155
C17—H17B···Cg2^iv	0.97	2.47	3.440 (3)	177
C20—H20A···Cg2^v	0.97	2.74	3.629 (3)	152

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

Acknowledgements

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

References

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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