Ethyl 6-methyl-3-(2-methyl-prop-1-en-yl)-2-oxo-4-phenyl-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

In the mol-ecule of the title compound, C(18)H(22)N(2)O(3), the dihydro-pyrimidinone ring adopts an envelope conformation. The dihedral angle between the phenyl ring and the mean plane through the enamine fragment is 86.04 (7)°. The mol-ecular conformation is stabilized by an intra-molecular C-H⋯O hydrogen bond. In the crystal, inter-molecular N-H⋯O hydrogen bonds link pairs of mol-ecules into centrosymmetric dimers.

Related literature

For general background to and pharmaceutical applications of pyrimidino­nes, see: Atwal (1990 ▶); Matsuda & Hirao (1965 ▶); Müller et al. (2008 ▶). For a related structure, see: Fun et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H22N2O3

M = 314.38

Monoclinic,

a = 14.114 (4) Å

b = 8.298 (2) Å

c = 14.629 (4) Å

β = 93.959 (2)°

V = 1709.3 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.25 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.979, T max = 0.982

11929 measured reflections

3180 independent reflections

2474 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.129

S = 0.96

3180 reflections

216 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042243/rz2648sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042243/rz2648Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811042243/rz2648Isup3.cml

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

C18H22N2O3	F(000) = 672
Mr = 314.38	Dx = 1.222 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4330 reflections
a = 14.114 (4) Å	θ = 2.8–26.4°
b = 8.298 (2) Å	µ = 0.08 mm−1
c = 14.629 (4) Å	T = 296 K
β = 93.959 (2)°	Block, colourless
V = 1709.3 (8) Å3	0.25 × 0.24 × 0.22 mm
Z = 4

Bruker APEXII CCD diffractometer	3180 independent reflections
Radiation source: fine-focus sealed tube	2474 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 25.5°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→17
Tmin = 0.979, Tmax = 0.982	k = −10→8
11929 measured reflections	l = −17→17

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ2(Fo2) + (0.0463P)2 + 1.3266P] where P = (Fo2 + 2Fc2)/3
3180 reflections	(Δ/σ)max = 0.001
216 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.33 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
C1	0.72325 (13)	0.1486 (2)	0.41220 (12)	0.0366 (4)
C2	0.77888 (13)	0.0257 (2)	0.44302 (13)	0.0388 (4)
C3	0.92081 (13)	0.1942 (2)	0.44340 (12)	0.0371 (4)
C4	0.76336 (12)	0.3183 (2)	0.41569 (13)	0.0365 (4)
H4	0.7332	0.3778	0.3636	0.044*
C5	0.62397 (14)	0.1386 (3)	0.37604 (14)	0.0437 (5)
C6	0.48677 (19)	−0.0234 (4)	0.3462 (2)	0.0869 (10)
H6A	0.4503	0.0676	0.3662	0.104*
H6B	0.4827	−0.0246	0.2798	0.104*
C7	0.4492 (2)	−0.1689 (5)	0.3797 (2)	0.1148 (14)
H7A	0.4801	−0.2590	0.3534	0.172*
H7B	0.3822	−0.1738	0.3631	0.172*
H7C	0.4598	−0.1723	0.4452	0.172*
C8	0.75390 (16)	−0.1477 (3)	0.45539 (18)	0.0582 (6)
H8A	0.6965	−0.1551	0.4867	0.087*
H8B	0.8045	−0.2006	0.4909	0.087*
H8C	0.7447	−0.1986	0.3965	0.087*
C9	0.91126 (13)	0.4621 (2)	0.38297 (14)	0.0423 (5)
H9	0.9533	0.5070	0.4277	0.051*
C10	0.89706 (15)	0.5394 (3)	0.30492 (15)	0.0497 (5)
C11	0.9448 (2)	0.7003 (3)	0.2919 (2)	0.0760 (8)
H11A	0.9780	0.7327	0.3485	0.114*
H11B	0.8977	0.7796	0.2738	0.114*
H11C	0.9891	0.6907	0.2453	0.114*
C12	0.8374 (2)	0.4801 (4)	0.22492 (17)	0.0868 (9)
H12A	0.8216	0.3690	0.2342	0.130*
H12B	0.8717	0.4900	0.1707	0.130*
H12C	0.7802	0.5427	0.2179	0.130*
C13	0.73992 (13)	0.4064 (2)	0.50270 (14)	0.0406 (5)
C14	0.79880 (18)	0.4024 (3)	0.58146 (16)	0.0579 (6)
H14	0.8564	0.3481	0.5816	0.070*
C15	0.7738 (2)	0.4779 (3)	0.66064 (19)	0.0778 (8)
H15	0.8146	0.4739	0.7133	0.093*
C16	0.6894 (2)	0.5584 (3)	0.6617 (2)	0.0795 (9)
H16	0.6726	0.6086	0.7150	0.095*
C17	0.6301 (2)	0.5647 (3)	0.5843 (2)	0.0730 (8)
H17	0.5726	0.6193	0.5849	0.088*
C18	0.65490 (15)	0.4902 (3)	0.50460 (18)	0.0551 (6)
H18	0.6143	0.4964	0.4519	0.066*
N1	0.87357 (11)	0.0582 (2)	0.46786 (12)	0.0415 (4)
N2	0.86624 (10)	0.31325 (18)	0.40381 (11)	0.0374 (4)
O1	1.00791 (9)	0.20302 (17)	0.45540 (10)	0.0488 (4)
O2	0.57967 (10)	0.2533 (2)	0.34516 (12)	0.0628 (5)
O3	0.58555 (10)	−0.0075 (2)	0.38094 (12)	0.0618 (5)
H1	0.9093 (16)	−0.018 (3)	0.4888 (15)	0.052 (6)*

	U11	U22	U33	U12	U13	U23
C1	0.0337 (10)	0.0370 (10)	0.0396 (10)	−0.0014 (8)	0.0047 (8)	0.0009 (8)
C2	0.0366 (10)	0.0362 (10)	0.0439 (10)	−0.0029 (8)	0.0062 (8)	0.0002 (8)
C3	0.0342 (10)	0.0368 (10)	0.0408 (10)	0.0020 (8)	0.0050 (8)	0.0024 (8)
C4	0.0295 (9)	0.0357 (10)	0.0444 (10)	0.0011 (8)	0.0028 (7)	0.0067 (8)
C5	0.0379 (11)	0.0466 (12)	0.0467 (11)	−0.0047 (9)	0.0040 (8)	−0.0024 (9)
C6	0.0550 (16)	0.082 (2)	0.120 (2)	−0.0265 (15)	−0.0249 (16)	0.0113 (18)
C7	0.086 (2)	0.162 (4)	0.094 (2)	−0.071 (2)	−0.0088 (18)	0.022 (2)
C8	0.0497 (13)	0.0388 (12)	0.0861 (17)	−0.0040 (10)	0.0037 (12)	0.0065 (11)
C9	0.0349 (10)	0.0401 (11)	0.0520 (12)	−0.0039 (8)	0.0029 (8)	0.0080 (9)
C10	0.0520 (12)	0.0454 (12)	0.0524 (12)	0.0005 (10)	0.0096 (10)	0.0089 (10)
C11	0.0805 (18)	0.0615 (16)	0.0869 (19)	−0.0118 (14)	0.0118 (15)	0.0278 (14)
C12	0.125 (3)	0.087 (2)	0.0479 (14)	−0.0181 (19)	0.0008 (15)	0.0073 (14)
C13	0.0396 (10)	0.0284 (10)	0.0548 (12)	−0.0030 (8)	0.0101 (9)	0.0036 (8)
C14	0.0628 (14)	0.0543 (14)	0.0564 (13)	0.0086 (12)	0.0015 (11)	−0.0065 (11)
C15	0.106 (2)	0.0690 (18)	0.0584 (15)	0.0009 (17)	0.0081 (15)	−0.0119 (13)
C16	0.106 (2)	0.0566 (17)	0.081 (2)	−0.0116 (16)	0.0432 (18)	−0.0182 (14)
C17	0.0653 (16)	0.0461 (14)	0.112 (2)	0.0006 (12)	0.0415 (16)	−0.0130 (15)
C18	0.0432 (12)	0.0420 (12)	0.0813 (16)	0.0004 (10)	0.0141 (11)	−0.0041 (11)
N1	0.0340 (9)	0.0335 (9)	0.0569 (10)	0.0033 (7)	0.0017 (7)	0.0096 (8)
N2	0.0305 (8)	0.0344 (9)	0.0476 (9)	0.0014 (7)	0.0051 (6)	0.0078 (7)
O1	0.0296 (7)	0.0477 (9)	0.0691 (9)	0.0014 (6)	0.0025 (6)	0.0112 (7)
O2	0.0429 (8)	0.0586 (10)	0.0841 (11)	0.0027 (8)	−0.0149 (8)	0.0068 (9)
O3	0.0425 (8)	0.0567 (10)	0.0846 (12)	−0.0162 (7)	−0.0085 (8)	0.0058 (8)

C1—C2	1.346 (3)	C9—C10	1.313 (3)
C1—C5	1.465 (3)	C9—N2	1.432 (2)
C1—C4	1.517 (3)	C9—H9	0.9300
C2—N1	1.387 (2)	C10—C12	1.478 (3)
C2—C8	1.495 (3)	C10—C11	1.514 (3)
C3—O1	1.232 (2)	C11—H11A	0.9600
C3—N2	1.357 (2)	C11—H11B	0.9600
C3—N1	1.371 (2)	C11—H11C	0.9600
C4—N2	1.475 (2)	C12—H12A	0.9600
C4—C13	1.524 (3)	C12—H12B	0.9600
C4—H4	0.9800	C12—H12C	0.9600
C5—O2	1.209 (2)	C13—C14	1.374 (3)
C5—O3	1.332 (3)	C13—C18	1.389 (3)
C6—C7	1.419 (4)	C14—C15	1.384 (3)
C6—O3	1.457 (3)	C14—H14	0.9300
C6—H6A	0.9700	C15—C16	1.366 (4)
C6—H6B	0.9700	C15—H15	0.9300
C7—H7A	0.9600	C16—C17	1.362 (4)
C7—H7B	0.9600	C16—H16	0.9300
C7—H7C	0.9600	C17—C18	1.386 (4)
C8—H8A	0.9600	C17—H17	0.9300
C8—H8B	0.9600	C18—H18	0.9300
C8—H8C	0.9600	N1—H1	0.85 (2)
C2—C1—C5	126.84 (18)	C9—C10—C11	119.8 (2)
C2—C1—C4	118.95 (16)	C12—C10—C11	115.4 (2)
C5—C1—C4	114.19 (16)	C10—C11—H11A	109.5
C1—C2—N1	118.06 (17)	C10—C11—H11B	109.5
C1—C2—C8	129.24 (18)	H11A—C11—H11B	109.5
N1—C2—C8	112.70 (17)	C10—C11—H11C	109.5
O1—C3—N2	123.30 (17)	H11A—C11—H11C	109.5
O1—C3—N1	120.66 (17)	H11B—C11—H11C	109.5
N2—C3—N1	116.02 (16)	C10—C12—H12A	109.5
N2—C4—C1	109.75 (15)	C10—C12—H12B	109.5
N2—C4—C13	112.60 (15)	H12A—C12—H12B	109.5
C1—C4—C13	111.80 (15)	C10—C12—H12C	109.5
N2—C4—H4	107.5	H12A—C12—H12C	109.5
C1—C4—H4	107.5	H12B—C12—H12C	109.5
C13—C4—H4	107.5	C14—C13—C18	118.0 (2)
O2—C5—O3	122.32 (18)	C14—C13—C4	122.37 (18)
O2—C5—C1	123.19 (19)	C18—C13—C4	119.65 (19)
O3—C5—C1	114.49 (18)	C13—C14—C15	121.1 (2)
C7—C6—O3	109.2 (3)	C13—C14—H14	119.4
C7—C6—H6A	109.8	C15—C14—H14	119.4
O3—C6—H6A	109.8	C16—C15—C14	120.2 (3)
C7—C6—H6B	109.8	C16—C15—H15	119.9
O3—C6—H6B	109.8	C14—C15—H15	119.9
H6A—C6—H6B	108.3	C17—C16—C15	119.7 (3)
C6—C7—H7A	109.5	C17—C16—H16	120.1
C6—C7—H7B	109.5	C15—C16—H16	120.1
H7A—C7—H7B	109.5	C16—C17—C18	120.4 (3)
C6—C7—H7C	109.5	C16—C17—H17	119.8
H7A—C7—H7C	109.5	C18—C17—H17	119.8
H7B—C7—H7C	109.5	C17—C18—C13	120.6 (2)
C2—C8—H8A	109.5	C17—C18—H18	119.7
C2—C8—H8B	109.5	C13—C18—H18	119.7
H8A—C8—H8B	109.5	C3—N1—C2	124.64 (17)
C2—C8—H8C	109.5	C3—N1—H1	114.6 (15)
H8A—C8—H8C	109.5	C2—N1—H1	119.2 (15)
H8B—C8—H8C	109.5	C3—N2—C9	118.14 (15)
C10—C9—N2	124.28 (19)	C3—N2—C4	120.31 (15)
C10—C9—H9	117.9	C9—N2—C4	117.11 (15)
N2—C9—H9	117.9	C5—O3—C6	116.56 (19)
C9—C10—C12	124.8 (2)
C5—C1—C2—N1	174.98 (18)	C15—C16—C17—C18	−0.1 (4)
C4—C1—C2—N1	−6.5 (3)	C16—C17—C18—C13	0.8 (4)
C5—C1—C2—C8	−5.1 (4)	C14—C13—C18—C17	−1.1 (3)
C4—C1—C2—C8	173.4 (2)	C4—C13—C18—C17	176.9 (2)
C2—C1—C4—N2	31.5 (2)	O1—C3—N1—C2	−168.31 (18)
C5—C1—C4—N2	−149.80 (16)	N2—C3—N1—C2	10.0 (3)
C2—C1—C4—C13	−94.2 (2)	C1—C2—N1—C3	−16.6 (3)
C5—C1—C4—C13	84.5 (2)	C8—C2—N1—C3	163.42 (19)
C2—C1—C5—O2	−176.1 (2)	O1—C3—N2—C9	−6.1 (3)
C4—C1—C5—O2	5.3 (3)	N1—C3—N2—C9	175.65 (16)
C2—C1—C5—O3	4.7 (3)	O1—C3—N2—C4	−161.77 (18)
C4—C1—C5—O3	−173.87 (17)	N1—C3—N2—C4	20.0 (3)
N2—C9—C10—C12	−4.0 (4)	C10—C9—N2—C3	134.3 (2)
N2—C9—C10—C11	177.0 (2)	C10—C9—N2—C4	−69.3 (3)
N2—C4—C13—C14	−33.4 (3)	C1—C4—N2—C3	−38.9 (2)
C1—C4—C13—C14	90.7 (2)	C13—C4—N2—C3	86.3 (2)
N2—C4—C13—C18	148.68 (18)	C1—C4—N2—C9	165.15 (16)
C1—C4—C13—C18	−87.2 (2)	C13—C4—N2—C9	−69.6 (2)
C18—C13—C14—C15	0.7 (3)	O2—C5—O3—C6	0.5 (3)
C4—C13—C14—C15	−177.2 (2)	C1—C5—O3—C6	179.7 (2)
C13—C14—C15—C16	0.0 (4)	C7—C6—O3—C5	−163.3 (3)
C14—C15—C16—C17	−0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2	0.93	2.58	3.176 (3)	123.
N1—H1···O1i	0.85 (2)	2.06 (2)	2.915 (2)	177 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2	0.93	2.58	3.176 (3)	123
N1—H1⋯O1i	0.85 (2)	2.06 (2)	2.915 (2)	177 (2)

Symmetry code: (i) .