N-Cyclo-hexyl-3-(4-hydr-oxy-6-oxo-1,6-dihydro-pyrimidin-5-yl)-3-p-tolyl-propanamide.

In the mol-ecule of the title compound, C(20)H(25)N(3)O(3), the aromatic rings are oriented at a dihedral angle of 88.36 (3)°. The cyclo-hexane ring adopts a chair conformation. In the crystal structure, inter-molecular N-H⋯O and O-H⋯N hydrogen bonds link the mol-ecules. C-H⋯π inter-actions 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 = 355.43

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.104

S = 1.02

3216 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.19 e Å−3

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 ▶).

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001251/hk2610Isup2.hkl

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

C20H25N3O3	F(000) = 760
Mr = 355.43	Dx = 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

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

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(Fo2) + (0.0354P)2] where P = (Fo2 + 2Fc2)/3
3216 reflections	(Δ/σ)max = 0.001
235 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg2iv	0.97	2.47	3.440 (3)	177
C20—H20A···Cg2v	0.97	2.74	3.629 (3)	152

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⋯Cg2iv	0.97	2.47	3.440 (3)	177
C20—H20A⋯Cg2v	0.97	2.74	3.629 (3)	152

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg2 is centroid of the C8–C13 ring.