1-[(Cyclo­propyl­meth­oxy)meth­yl]-5-ethyl-6-(4-methyl­benzyl)-1,2,3,4-tetra­hydro­pyrimidine-2,4-dione

El-Brollosy, N.R.; El-Emam, A.A.; Al-Deeb, O.A.; Ng, S.W.

doi:10.1107/S1600536811055681

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o348

doi:10.1107/S1600536811055681

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1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6-(4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione

Nasser R. El-Brollosy,^a Ali A. El-Emam,^a Omar A. Al-Deeb ^a and Seik Weng Ng ^b,^c ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 December 2011; accepted 26 December 2011; online 11 January 2012)

The pyrimidine ring in the title compound, C₁₉H₂₄N₂O₃, 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 molecule, the hydrogen bond generating an inversion dimer. The cyclopropyl 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_r = 328.40
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.155
S = 1.06
4006 reflections
232 parameters
20 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) -x+1, -y+1, -z+1.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811055681/xu5423sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811055681/xu5423Isup3.cml

checkCIF report

Comment top

The compound (Scheme I) was synthesized for an evaluation of its anti-viral activity against HIV-1 (El-Brollosy et al., 2009). The pyrimidine ring is nearly planar; 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 (Fig. 1). The amino group is hydrogen-bond donor to the exocyclic O atom at the 2-position, the hydrogen bond generating a centrosymmetric dimer (Table 1, Fig. 2).

Related literature top

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

Experimental top

The compound (Scheme I) was synthesized by using a reported method (El-Brollosy et al., 2009), and was recrystallized from ethanol.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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).

Figures top

	Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C₁₉H₂₄N₂O₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder is not shown.
	Fig. 2. Dimeric hydrogen-bonded structure.

1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6-(4-methylbenzyl)-1,2,3,4- tetrahydropyrimidine-2,4-dione top

Crystal data top

C₁₉H₂₄N₂O₃	F(000) = 1408
M_r = 328.40	D_x = 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

Data collection top

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 monochromator	R_int = 0.044
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.6°
ω scan	h = −20→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −7→10
T_min = 0.979, T_max = 0.987	l = −35→21
7060 measured reflections

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)] = 0.061	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(F_o²) + (0.0471P)² + 1.5059P] where P = (F_o² + 2F_c²)/3
4006 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.22 e Å⁻³
20 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₉H₂₄N₂O₃	V = 3484.2 (5) Å³
M_r = 328.40	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 15.6080 (13) Å	µ = 0.09 mm⁻¹
b = 8.1330 (6) Å	T = 100 K
c = 27.496 (2) Å	0.25 × 0.20 × 0.15 mm
β = 93.397 (7)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4006 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2446 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.987	R_int = 0.044
7060 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	20 restraints
wR(F²) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.22 e Å⁻³
4006 reflections	Δρ_min = −0.26 e Å⁻³
232 parameters

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

	x	y	z	U_iso*/U_eq	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₄N₂O₃
M_r	328.40
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	15.6080 (13), 8.1330 (6), 27.496 (2)
β (°)	93.397 (7)
V (Å³)	3484.2 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.979, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7060, 4006, 2446
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.155, 1.06
No. of reflections	4006
No. of parameters	232
No. of restraints	20
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.26

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Acknowledgements

We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, and the University of Malaya for supporting this study.

References

Agilent (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
El-Brollosy, N. R., Al-Deeb, O. A., El-Emam, A. A., Pedersen, E. B., La Colla, P., Collu, G., Sanna, G. & Loddo, R. (2009). Arch. Pharm. Chem. Life Sci. 342, 663–670. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 2| February 2012| Page o348

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

1-[(Cyclo­propyl­meth­­oxy)meth­yl]-5-ethyl-6-(4-methyl­benzyl)-1,2,3,4-tetra­hydro­pyrimidine-2,4-dione

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1-[(Cyclopropylmethoxy)methyl]-5-ethyl-6-(4-methylbenzyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione