1-[(Cyclo-propyl-meth-oxy)meth-yl]-5-ethyl-6-(4-methyl-benzyl)-1,2,3,4-tetra-hydro-pyrimidine-2,4-dione.

The pyrimidine ring in the title compound, C(19)H(24)N(2)O(3), is nearly planar (r.m.s. deviation = 0.008 Å); the C atom at the 5-position deviates by 0.054 (3) Å from the mean plane and the C atom at the 6-position by 0.006 (3) Å in the opposite direction. The benzene ring is approximately perpendicular to the pyrimidine ring [dihedral angle = 83.90 (10)°]. The amino group is hydrogen-bond donor to the exocyclic O atom at the 2-position of an adjacent mol-ecule, the hydrogen bond generating an inversion dimer. The cyclo-propyl ring is disordered over two sets of sites with the major component having 71.5 (4)% occupancy.

Related literature

For the synthesis, see: El-Brollosy et al. (2009 ▶).

Experimental

Crystal data

C19H24N2O3

M = 328.40

Monoclinic,

a = 15.6080 (13) Å

b = 8.1330 (6) Å

c = 27.496 (2) Å

β = 93.397 (7)°

V = 3484.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.979, T max = 0.987

7060 measured reflections

4006 independent reflections

2446 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.155

S = 1.06

4006 reflections

232 parameters

20 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811055681/xu5423sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055681/xu5423Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055681/xu5423Isup3.cml

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

C19H24N2O3	F(000) = 1408
Mr = 328.40	Dx = 1.252 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1703 reflections
a = 15.6080 (13) Å	θ = 2.6–27.5°
b = 8.1330 (6) Å	µ = 0.09 mm−1
c = 27.496 (2) Å	T = 100 K
β = 93.397 (7)°	Irregular, colorless
V = 3484.2 (5) Å3	0.25 × 0.20 × 0.15 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	4006 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	2446 reflections with I > 2σ(I)
Mirror	Rint = 0.044
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scan	h = −20→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −7→10
Tmin = 0.979, Tmax = 0.987	l = −35→21
7060 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0471P)2 + 1.5059P] where P = (Fo2 + 2Fc2)/3
4006 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 0.22 e Å−3
20 restraints	Δρmin = −0.26 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.50675 (10)	0.53293 (18)	0.43772 (5)	0.0306 (4)
O2	0.72573 (10)	0.51944 (19)	0.55353 (6)	0.0337 (4)
O3	0.61688 (10)	0.75562 (18)	0.34641 (5)	0.0322 (4)
N1	0.61833 (12)	0.5257 (2)	0.49464 (7)	0.0252 (4)
H1	0.5798 (12)	0.508 (3)	0.5165 (7)	0.036 (7)*
N2	0.64326 (12)	0.5688 (2)	0.41308 (6)	0.0251 (4)
C1	0.58460 (15)	0.5419 (3)	0.44798 (8)	0.0256 (5)
C2	0.70469 (15)	0.5330 (2)	0.51006 (8)	0.0260 (5)
C3	0.76385 (15)	0.5573 (3)	0.47165 (8)	0.0261 (5)
C4	0.73229 (15)	0.5764 (2)	0.42504 (8)	0.0253 (5)
C5	0.85735 (15)	0.5580 (3)	0.48899 (9)	0.0316 (6)
H5A	0.8648	0.6277	0.5184	0.038*
H5B	0.8913	0.6074	0.4634	0.038*
C6	0.89235 (16)	0.3854 (3)	0.50097 (10)	0.0394 (6)
H6A	0.9522	0.3936	0.5136	0.059*
H6B	0.8891	0.3180	0.4714	0.059*
H6C	0.8580	0.3344	0.5256	0.059*
C7	0.78826 (15)	0.6035 (3)	0.38279 (8)	0.0306 (6)
H7A	0.8437	0.6504	0.3954	0.037*
H7B	0.7603	0.6858	0.3606	0.037*
C8	0.80601 (14)	0.4493 (3)	0.35365 (8)	0.0286 (5)
C9	0.80732 (16)	0.2935 (3)	0.37445 (9)	0.0354 (6)
H9	0.7922	0.2810	0.4072	0.043*
C10	0.83032 (16)	0.1554 (3)	0.34834 (8)	0.0354 (6)
H10	0.8311	0.0506	0.3636	0.042*
C11	0.85223 (15)	0.1686 (3)	0.30026 (8)	0.0331 (6)
C12	0.84815 (15)	0.3240 (3)	0.27877 (9)	0.0369 (6)
H12	0.8607	0.3357	0.2456	0.044*
C13	0.82606 (15)	0.4618 (3)	0.30501 (8)	0.0340 (6)
H13	0.8246	0.5664	0.2896	0.041*
C14	0.87809 (17)	0.0183 (3)	0.27244 (9)	0.0457 (7)
H14A	0.9128	0.0518	0.2456	0.069*
H14B	0.8265	−0.0390	0.2593	0.069*
H14C	0.9117	−0.0554	0.2944	0.069*
C15	0.60855 (15)	0.5928 (3)	0.36212 (8)	0.0285 (5)
H15A	0.6393	0.5192	0.3404	0.034*
H15B	0.5471	0.5617	0.3597	0.034*
C16	0.55665 (16)	0.8680 (3)	0.36619 (9)	0.0326 (6)
H16A	0.5479	0.8404	0.4006	0.039*	0.715 (4)
H16B	0.5006	0.8618	0.3474	0.039*	0.715 (4)
H16C	0.5778	0.8995	0.3995	0.039*	0.285 (4)
H16D	0.5009	0.8113	0.3686	0.039*	0.285 (4)
C17	0.5939 (2)	1.0366 (4)	0.36259 (12)	0.0311 (8)	0.715 (4)
H17	0.6480	1.0583	0.3829	0.037*	0.715 (4)
C18	0.5821 (3)	1.1319 (4)	0.31577 (14)	0.0401 (9)	0.715 (4)
H18A	0.6284	1.2083	0.3074	0.048*	0.715 (4)
H18B	0.5518	1.0771	0.2876	0.048*	0.715 (4)
C19	0.5321 (8)	1.1730 (14)	0.3578 (5)	0.0357 (18)	0.715 (4)
H19A	0.4703	1.1451	0.3558	0.043*	0.715 (4)
H19B	0.5467	1.2760	0.3756	0.043*	0.715 (4)
C17'	0.5430 (5)	1.0209 (9)	0.3360 (3)	0.0311 (8)	0.285
H17'	0.5189	1.0059	0.3018	0.037*	0.285 (4)
C18'	0.6114 (7)	1.1436 (12)	0.3439 (4)	0.0401 (9)	0.285
H18C	0.6306	1.2021	0.3149	0.048*	0.285 (4)
H18D	0.6579	1.1186	0.3688	0.048*	0.285 (4)
C19'	0.521 (2)	1.192 (4)	0.3624 (15)	0.0357 (18)	0.285
H19C	0.4865	1.2742	0.3436	0.043*	0.285 (4)
H19D	0.5140	1.1902	0.3979	0.043*	0.285 (4)

	U11	U22	U33	U12	U13	U23
O1	0.0354 (10)	0.0381 (9)	0.0179 (8)	−0.0015 (7)	−0.0004 (7)	0.0037 (7)
O2	0.0468 (10)	0.0358 (9)	0.0176 (9)	−0.0012 (8)	−0.0050 (7)	0.0035 (7)
O3	0.0479 (10)	0.0299 (8)	0.0192 (9)	0.0014 (8)	0.0055 (7)	0.0056 (7)
N1	0.0359 (11)	0.0256 (10)	0.0140 (10)	−0.0014 (9)	0.0009 (8)	0.0030 (8)
N2	0.0356 (11)	0.0265 (9)	0.0131 (9)	−0.0029 (8)	0.0007 (8)	0.0014 (7)
C1	0.0378 (14)	0.0231 (11)	0.0158 (11)	−0.0015 (10)	0.0010 (10)	0.0027 (9)
C2	0.0398 (14)	0.0184 (10)	0.0191 (12)	0.0003 (10)	−0.0039 (10)	−0.0001 (9)
C3	0.0359 (13)	0.0212 (11)	0.0210 (12)	−0.0011 (10)	−0.0005 (10)	0.0005 (9)
C4	0.0352 (13)	0.0181 (10)	0.0226 (12)	−0.0026 (10)	0.0009 (10)	0.0005 (9)
C5	0.0388 (14)	0.0276 (12)	0.0278 (13)	−0.0026 (11)	−0.0029 (10)	0.0041 (10)
C6	0.0416 (15)	0.0349 (14)	0.0408 (16)	0.0035 (12)	−0.0052 (12)	0.0027 (11)
C7	0.0381 (14)	0.0317 (12)	0.0221 (13)	−0.0057 (11)	0.0034 (10)	0.0044 (10)
C8	0.0297 (12)	0.0378 (13)	0.0183 (12)	−0.0035 (10)	0.0008 (9)	−0.0004 (10)
C9	0.0492 (16)	0.0383 (14)	0.0193 (13)	0.0005 (12)	0.0066 (11)	−0.0012 (10)
C10	0.0508 (15)	0.0362 (13)	0.0191 (13)	0.0040 (12)	0.0018 (11)	−0.0009 (10)
C11	0.0303 (13)	0.0510 (15)	0.0177 (12)	0.0049 (11)	−0.0034 (9)	−0.0066 (11)
C12	0.0370 (14)	0.0591 (17)	0.0148 (12)	−0.0020 (12)	0.0027 (10)	0.0015 (11)
C13	0.0366 (13)	0.0446 (14)	0.0205 (13)	−0.0051 (12)	−0.0001 (10)	0.0044 (11)
C14	0.0458 (16)	0.0653 (18)	0.0256 (14)	0.0110 (14)	−0.0011 (12)	−0.0125 (13)
C15	0.0421 (14)	0.0308 (12)	0.0124 (11)	−0.0009 (11)	−0.0007 (10)	0.0016 (9)
C16	0.0436 (15)	0.0329 (13)	0.0211 (13)	0.0016 (11)	0.0018 (10)	0.0042 (10)
C17	0.0378 (18)	0.0338 (17)	0.0212 (17)	−0.0049 (15)	−0.0034 (12)	0.0026 (14)
C18	0.058 (2)	0.0379 (18)	0.024 (2)	0.0008 (18)	0.0071 (16)	0.0057 (18)
C19	0.045 (4)	0.025 (3)	0.038 (3)	0.006 (2)	0.009 (2)	−0.004 (2)
C17'	0.0378 (18)	0.0338 (17)	0.0212 (17)	−0.0049 (15)	−0.0034 (12)	0.0026 (14)
C18'	0.058 (2)	0.0379 (18)	0.024 (2)	0.0008 (18)	0.0071 (16)	0.0057 (18)
C19'	0.045 (4)	0.025 (3)	0.038 (3)	0.006 (2)	0.009 (2)	−0.004 (2)

O1—C1	1.233 (3)	C12—C13	1.387 (3)
O2—C2	1.226 (2)	C12—H12	0.9500
O3—C15	1.401 (3)	C13—H13	0.9500
O3—C16	1.440 (3)	C14—H14A	0.9800
N1—C1	1.364 (3)	C14—H14B	0.9800
N1—C2	1.390 (3)	C14—H14C	0.9800
N1—H1	0.887 (10)	C15—H15A	0.9900
N2—C1	1.382 (3)	C15—H15B	0.9900
N2—C4	1.410 (3)	C16—C17	1.495 (4)
N2—C15	1.485 (3)	C16—C17'	1.503 (7)
C2—C3	1.457 (3)	C16—H16A	0.9900
C3—C4	1.354 (3)	C16—H16B	0.9900
C3—C5	1.508 (3)	C16—H16C	0.9900
C4—C7	1.511 (3)	C16—H16D	0.9900
C5—C6	1.535 (3)	C17—C19	1.471 (12)
C5—H5A	0.9900	C17—C18	1.505 (5)
C5—H5B	0.9900	C17—H17	1.0000
C6—H6A	0.9800	C18—C19	1.472 (12)
C6—H6B	0.9800	C18—H18A	0.9900
C6—H6C	0.9800	C18—H18B	0.9900
C7—C8	1.523 (3)	C19—H19A	0.9900
C7—H7A	0.9900	C19—H19B	0.9900
C7—H7B	0.9900	C17'—C18'	1.468 (14)
C8—C9	1.390 (3)	C17'—C19'	1.61 (3)
C8—C13	1.395 (3)	C17'—H17'	1.0000
C9—C10	1.391 (3)	C18'—C19'	1.57 (3)
C9—H9	0.9500	C18'—H18C	0.9900
C10—C11	1.389 (3)	C18'—H18D	0.9900
C10—H10	0.9500	C19'—H19C	0.9900
C11—C12	1.395 (3)	C19'—H19D	0.9900
C11—C14	1.509 (3)
C15—O3—C16	114.11 (17)	H14A—C14—H14C	109.5
C1—N1—C2	126.6 (2)	H14B—C14—H14C	109.5
C1—N1—H1	114.4 (16)	O3—C15—N2	112.32 (17)
C2—N1—H1	119.0 (16)	O3—C15—H15A	109.1
C1—N2—C4	121.93 (18)	N2—C15—H15A	109.1
C1—N2—C15	117.14 (18)	O3—C15—H15B	109.1
C4—N2—C15	120.92 (18)	N2—C15—H15B	109.1
O1—C1—N1	122.0 (2)	H15A—C15—H15B	107.9
O1—C1—N2	122.3 (2)	O3—C16—C17	107.0 (2)
N1—C1—N2	115.7 (2)	O3—C16—C17'	113.0 (4)
O2—C2—N1	119.5 (2)	O3—C16—H16A	110.3
O2—C2—C3	125.1 (2)	C17—C16—H16A	110.3
N1—C2—C3	115.44 (19)	C17'—C16—H16A	133.8
C4—C3—C2	119.4 (2)	O3—C16—H16B	110.3
C4—C3—C5	126.1 (2)	C17—C16—H16B	110.3
C2—C3—C5	114.5 (2)	H16A—C16—H16B	108.6
C3—C4—N2	120.9 (2)	O3—C16—H16C	109.0
C3—C4—C7	123.4 (2)	C17—C16—H16C	73.4
N2—C4—C7	115.69 (19)	C17'—C16—H16C	109.0
C3—C5—C6	112.95 (19)	O3—C16—H16D	109.0
C3—C5—H5A	109.0	C17'—C16—H16D	109.0
C6—C5—H5A	109.0	H16C—C16—H16D	107.8
C3—C5—H5B	109.0	C19—C17—C16	116.2 (5)
C6—C5—H5B	109.0	C19—C17—C18	59.3 (6)
H5A—C5—H5B	107.8	C16—C17—C18	120.0 (3)
C5—C6—H6A	109.5	C19—C17—H17	116.3
C5—C6—H6B	109.5	C16—C17—H17	116.3
H6A—C6—H6B	109.5	C18—C17—H17	116.3
C5—C6—H6C	109.5	C19—C18—C17	59.2 (6)
H6A—C6—H6C	109.5	C19—C18—H18A	117.8
H6B—C6—H6C	109.5	C17—C18—H18A	117.8
C4—C7—C8	114.55 (18)	C19—C18—H18B	117.8
C4—C7—H7A	108.6	C17—C18—H18B	117.8
C8—C7—H7A	108.6	H18A—C18—H18B	115.0
C4—C7—H7B	108.6	C18—C19—C17	61.5 (4)
C8—C7—H7B	108.6	C18—C19—H19A	117.6
H7A—C7—H7B	107.6	C17—C19—H19A	117.6
C9—C8—C13	117.5 (2)	C18—C19—H19B	117.6
C9—C8—C7	122.2 (2)	C17—C19—H19B	117.6
C13—C8—C7	120.2 (2)	H19A—C19—H19B	114.7
C8—C9—C10	121.4 (2)	C18'—C17'—C16	113.8 (7)
C8—C9—H9	119.3	C18'—C17'—C19'	61.3 (12)
C10—C9—H9	119.3	C16—C17'—C19'	119.4 (16)
C11—C10—C9	120.9 (2)	C18'—C17'—H17'	116.8
C11—C10—H10	119.5	C16—C17'—H17'	116.8
C9—C10—H10	119.5	C19'—C17'—H17'	116.8
C10—C11—C12	117.7 (2)	C17'—C18'—C19'	63.9 (12)
C10—C11—C14	120.5 (2)	C17'—C18'—H18C	117.4
C12—C11—C14	121.7 (2)	C19'—C18'—H18C	117.4
C13—C12—C11	121.2 (2)	C17'—C18'—H18D	117.4
C13—C12—H12	119.4	C19'—C18'—H18D	117.4
C11—C12—H12	119.4	H18C—C18'—H18D	114.4
C12—C13—C8	121.1 (2)	C18'—C19'—C17'	54.9 (12)
C12—C13—H13	119.5	C18'—C19'—H19C	118.3
C8—C13—H13	119.5	C17'—C19'—H19C	118.3
C11—C14—H14A	109.5	C18'—C19'—H19D	118.3
C11—C14—H14B	109.5	C17'—C19'—H19D	118.3
H14A—C14—H14B	109.5	H19C—C19'—H19D	115.5
C11—C14—H14C	109.5
C2—N1—C1—O1	179.7 (2)	C7—C8—C9—C10	−174.8 (2)
C2—N1—C1—N2	−0.2 (3)	C8—C9—C10—C11	−0.5 (4)
C4—N2—C1—O1	−178.97 (19)	C9—C10—C11—C12	−1.6 (4)
C15—N2—C1—O1	2.1 (3)	C9—C10—C11—C14	179.3 (2)
C4—N2—C1—N1	0.9 (3)	C10—C11—C12—C13	2.3 (4)
C15—N2—C1—N1	−177.95 (17)	C14—C11—C12—C13	−178.6 (2)
C1—N1—C2—O2	178.59 (19)	C11—C12—C13—C8	−0.9 (4)
C1—N1—C2—C3	−1.3 (3)	C9—C8—C13—C12	−1.3 (3)
O2—C2—C3—C4	−177.7 (2)	C7—C8—C13—C12	175.6 (2)
N1—C2—C3—C4	2.2 (3)	C16—O3—C15—N2	−75.0 (2)
O2—C2—C3—C5	2.4 (3)	C1—N2—C15—O3	109.0 (2)
N1—C2—C3—C5	−177.65 (17)	C4—N2—C15—O3	−69.9 (2)
C2—C3—C4—N2	−1.7 (3)	C15—O3—C16—C17	158.4 (2)
C5—C3—C4—N2	178.21 (19)	C15—O3—C16—C17'	−158.1 (4)
C2—C3—C4—C7	179.5 (2)	O3—C16—C17—C19	151.7 (6)
C5—C3—C4—C7	−0.7 (3)	C17'—C16—C17—C19	45.9 (8)
C1—N2—C4—C3	0.0 (3)	O3—C16—C17—C18	83.6 (3)
C15—N2—C4—C3	178.87 (18)	C17'—C16—C17—C18	−22.2 (5)
C1—N2—C4—C7	178.97 (19)	C16—C17—C18—C19	104.5 (6)
C15—N2—C4—C7	−2.2 (3)	C16—C17—C19—C18	−110.9 (4)
C4—C3—C5—C6	−104.2 (2)	O3—C16—C17'—C18'	−79.3 (7)
C2—C3—C5—C6	75.6 (3)	C17—C16—C17'—C18'	10.5 (5)
C3—C4—C7—C8	98.1 (2)	O3—C16—C17'—C19'	−148.5 (14)
N2—C4—C7—C8	−80.8 (2)	C17—C16—C17'—C19'	−58.7 (15)
C4—C7—C8—C9	−28.4 (3)	C16—C17'—C18'—C19'	−111.8 (18)
C4—C7—C8—C13	154.9 (2)	C16—C17'—C19'—C18'	102.6 (12)
C13—C8—C9—C10	1.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.89 (1)	1.93 (1)	2.816 (2)	178 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.89 (1)	1.93 (1)	2.816 (2)	178 (2)

Symmetry code: (i) .