6-(3,5-Dimethyl­benz­yl)-5-ethyl-1-[(2-phen­oxy­eth­oxy)meth­yl]-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/S1600536811039821

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2839

doi:10.1107/S1600536811039821

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6-(3,5-Dimethylbenzyl)-5-ethyl-1-[(2-phenoxyethoxy)methyl]-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, PO Box 2457 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 26 September 2011; accepted 28 September 2011; online 5 October 2011)

The six-membered ring of the uracil part of the title compound, C₂₄H₂₈N₂O₄, is nearly planar (r.m.s. deviation = 0.013 Å); the aromatic ring of the 3,5-dimethylbenzyl substitutent is aligned at 85.4 (1)° with respect to this mean plane. The phenyl ring of the substituent at the 1-position takes up two orientations in a 1:1 ratio. In the crystal, two molecules are liked by a pair of N—H⋯O hydrogen bonds, generating a centrosymmetric hydrogen-bonded dimer.

Related literature

For the background to our studies on antiviral HIV chemicals, see: El-Brollosy et al. (2007 , 2008 , 2009 ).

Experimental

Crystal data

C₂₄H₂₈N₂O₄
M_r = 408.48
Monoclinic, P 2₁ /n
a = 16.1116 (6) Å
b = 4.8211 (2) Å
c = 27.5125 (10) Å
β = 92.574 (3)°
V = 2134.90 (14) Å³
Z = 4
Cu Kα radiation
μ = 0.70 mm⁻¹
T = 100 K
0.20 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.873, T_max = 0.966
6587 measured reflections
4115 independent reflections
2940 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.130
S = 1.03
4115 reflections
272 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.33 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.92 (3)	1.94 (3)	2.859 (2)	173 (2)
Symmetry code: (i) -x+1, -y+2, -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/S1600536811039821/xu5341sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811039821/xu5341Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811039821/xu5341Isup3.cml

checkCIF report

Comment top

Non-nucleoside reverse transcriptase inhibitors (NNRTIs) are chemicals for treating the human immunodeficiency virus (HIV), and the synthesis of such compounds represents a major thrust of our studies. We have synthesized several analogs of emivirine, TNK-651 and GCA-186 (El-Brollosy et al., 2007; 2008; 2009). We have synthesized the title compound (Scheme I) as a GCA-186 analog but with phenoxyethoxymethyl and ethyl substituents instead of ethoxymethyl and isopropyl at the 1- and 5-positions. Its antiviral activity against HIV will be reported elsewhere.

The six-membered ring of the uracil part is planar. The aromatic ring of the 3,5-dimethylbenzyl substitutent is aligned at 85.4 (1)° with respect to this plane. The phenyl ring of the substituent at the 1-position is disordered over two orientations in a 1:1 ratio (Fig. 1). Two molecules are liked by an N–H···O hydrogen bond to generate a centrosymmetric hydrogen-bonded dimer (Table 1).

Related literature top

For the background to our studies on antiviral HIV chemicals, see: El-Brollosy et al. (2007, 2008, 2009).

Experimental top

5-Ethyl-6-(3,5-dimethylbenzyl)uracil (0.258 g,1 mmol) was stirred in anhydrous acetontrile (15 ml) under nitrogen and N,O-bis(trimethylsilyl)acetamide (0.87 ml, 3.5 mol) was added. The clear solution -50° C and trimethylsilyl trifluoromethanesulfonate (0.18 ml, 1 mmol) was added followed by the dropwise addition of bis-(phenoxyethyloxy)methane (0.576 mg, 2 mmol). The mixture was stirred at room temperature for 4 h. The reaction was quenched with saturate sodium bicarbonate soluiton (5 ml). The solvent was evaporated under reduced pressure. The residue was extracted with ether (3 x 50 ml); the combined organic fractions were dried over magnesium sulfate. The solvent was removed and the residue was chromatographed on silica gel column with chloroform to afford a white solid. This was recrystallized from ethanol to yield the title compound as colorless crystals.

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 C₂₄H₂₈N₂O₄ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. The disorder in the phenyl ring is not shown.

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

Crystal data top

C₂₄H₂₈N₂O₄	F(000) = 872
M_r = 408.48	D_x = 1.271 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 1976 reflections
a = 16.1116 (6) Å	θ = 2.7–74.3°
b = 4.8211 (2) Å	µ = 0.70 mm⁻¹
c = 27.5125 (10) Å	T = 100 K
β = 92.574 (3)°	Prism, colorless
V = 2134.90 (14) Å³	0.20 × 0.10 × 0.05 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4115 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2940 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.036
Detector resolution: 10.4041 pixels mm^-1	θ_max = 74.4°, θ_min = 3.1°
ω scans	h = −17→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −5→5
T_min = 0.873, T_max = 0.966	l = −19→34
6587 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0602P)²] where P = (F_o² + 2F_c²)/3
4115 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.20 e Å⁻³
1 restraint	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₄H₂₈N₂O₄	V = 2134.90 (14) Å³
M_r = 408.48	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 16.1116 (6) Å	µ = 0.70 mm⁻¹
b = 4.8211 (2) Å	T = 100 K
c = 27.5125 (10) Å	0.20 × 0.10 × 0.05 mm
β = 92.574 (3)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4115 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	2940 reflections with I > 2σ(I)
T_min = 0.873, T_max = 0.966	R_int = 0.036
6587 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
4115 reflections	Δρ_min = −0.33 e Å⁻³
272 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.41200 (10)	0.7342 (4)	0.49973 (5)	0.0225 (4)
H1	0.4438 (15)	0.827 (5)	0.4779 (8)	0.048 (7)*
N2	0.38205 (9)	0.6427 (3)	0.58001 (5)	0.0188 (3)
O1	0.34103 (8)	0.5312 (3)	0.43648 (4)	0.0288 (3)
O2	0.48232 (8)	0.9577 (3)	0.56125 (4)	0.0268 (3)
O3	0.44380 (7)	0.4797 (3)	0.65593 (4)	0.0248 (3)
O4	0.56832 (8)	0.5868 (3)	0.72760 (5)	0.0324 (4)
C1	0.35269 (11)	0.5509 (4)	0.48060 (6)	0.0207 (4)
C2	0.30735 (11)	0.3942 (4)	0.51623 (6)	0.0200 (4)
C3	0.24618 (11)	0.1866 (5)	0.49479 (7)	0.0265 (5)
H3A	0.2372	0.0400	0.5192	0.032*
H3B	0.2706	0.0976	0.4663	0.032*
C4	0.16242 (13)	0.3118 (6)	0.47889 (8)	0.0397 (6)
H4A	0.1283	0.1710	0.4618	0.060*
H4B	0.1711	0.4688	0.4571	0.060*
H4C	0.1341	0.3762	0.5076	0.060*
C5	0.32268 (11)	0.4450 (4)	0.56414 (6)	0.0187 (4)
C6	0.42908 (11)	0.7878 (4)	0.54791 (6)	0.0204 (4)
C7	0.27874 (11)	0.2963 (4)	0.60376 (6)	0.0208 (4)
H7A	0.3209	0.2359	0.6288	0.025*
H7B	0.2525	0.1271	0.5896	0.025*
C8	0.21249 (11)	0.4626 (4)	0.62863 (6)	0.0201 (4)
C9	0.16152 (11)	0.6537 (4)	0.60390 (6)	0.0210 (4)
H9	0.1699	0.6903	0.5705	0.025*
C10	0.09878 (11)	0.7921 (4)	0.62691 (7)	0.0244 (4)
C11	0.08768 (12)	0.7369 (4)	0.67617 (7)	0.0267 (5)
H11	0.0455	0.8325	0.6925	0.032*
C12	0.13705 (11)	0.5453 (4)	0.70170 (6)	0.0244 (4)
C13	0.19980 (11)	0.4113 (4)	0.67758 (6)	0.0229 (4)
H13	0.2346	0.2825	0.6949	0.028*
C14	0.04326 (12)	0.9954 (5)	0.59964 (8)	0.0326 (5)
H14A	0.0550	0.9909	0.5650	0.049*
H14B	0.0535	1.1826	0.6125	0.049*
H14C	−0.0150	0.9453	0.6037	0.049*
C15	0.12262 (13)	0.4790 (5)	0.75430 (7)	0.0335 (5)
H15A	0.1071	0.6487	0.7713	0.050*
H15B	0.1736	0.4029	0.7698	0.050*
H15C	0.0778	0.3424	0.7560	0.050*
C16	0.39924 (11)	0.6934 (4)	0.63250 (6)	0.0212 (4)
H16A	0.4311	0.8682	0.6365	0.025*
H16B	0.3458	0.7180	0.6484	0.025*
C17	0.53086 (11)	0.4743 (5)	0.64639 (7)	0.0297 (5)
H17A	0.5493	0.6616	0.6368	0.036*
H17B	0.5406	0.3453	0.6192	0.036*
C18	0.57914 (12)	0.3821 (5)	0.69086 (7)	0.0317 (5)
H18A	0.5587	0.1998	0.7018	0.038*
H18B	0.6387	0.3638	0.6840	0.038*
C19	0.6138 (7)	0.580 (2)	0.7701 (2)	0.0314 (7)	0.50
C20	0.6750 (6)	0.3880 (17)	0.7837 (2)	0.0428 (16)	0.50
H20	0.6865	0.2373	0.7628	0.051*	0.50
C21	0.7193 (4)	0.4169 (15)	0.8279 (2)	0.0473 (14)	0.50
H21	0.7611	0.2860	0.8373	0.057*	0.50
C22	0.7025 (4)	0.6374 (15)	0.85853 (18)	0.0386 (18)	0.50
H22	0.7328	0.6572	0.8888	0.046*	0.50
C23	0.6413 (6)	0.8290 (14)	0.8449 (2)	0.0400 (17)	0.50
H23	0.6298	0.9797	0.8658	0.048*	0.50
C24	0.5969 (7)	0.800 (2)	0.8007 (2)	0.0365 (14)	0.50
H24	0.5551	0.9309	0.7914	0.044*	0.50
C19'	0.6218 (7)	0.570 (2)	0.7688 (2)	0.0314 (7)	0.50
C20'	0.6910 (6)	0.3974 (18)	0.7719 (2)	0.0428 (16)	0.50
H20'	0.7033	0.2811	0.7453	0.051*	0.50
C21'	0.7423 (4)	0.3952 (17)	0.8139 (2)	0.0473 (14)	0.50
H21'	0.7896	0.2774	0.8160	0.057*	0.50
C22'	0.7244 (4)	0.5654 (18)	0.85281 (19)	0.0386 (18)	0.50
H22'	0.7594	0.5639	0.8815	0.046*	0.50
C23'	0.6552 (5)	0.7379 (15)	0.84974 (19)	0.0400 (17)	0.50
H23'	0.6429	0.8542	0.8764	0.048*	0.50
C24'	0.6039 (6)	0.740 (2)	0.8077 (2)	0.0365 (14)	0.50
H24'	0.5566	0.8579	0.8056	0.044*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0214 (8)	0.0306 (10)	0.0160 (7)	−0.0053 (7)	0.0047 (6)	0.0009 (7)
N2	0.0188 (7)	0.0235 (9)	0.0142 (7)	−0.0030 (7)	0.0028 (6)	−0.0016 (7)
O1	0.0305 (7)	0.0412 (9)	0.0151 (6)	−0.0050 (7)	0.0035 (5)	−0.0015 (6)
O2	0.0257 (7)	0.0348 (8)	0.0202 (6)	−0.0111 (6)	0.0040 (5)	0.0003 (6)
O3	0.0187 (6)	0.0374 (8)	0.0182 (6)	0.0007 (6)	0.0013 (5)	0.0028 (6)
O4	0.0285 (7)	0.0444 (9)	0.0235 (7)	0.0064 (7)	−0.0068 (6)	−0.0081 (7)
C1	0.0197 (9)	0.0259 (11)	0.0166 (9)	0.0023 (8)	0.0032 (7)	0.0006 (8)
C2	0.0184 (9)	0.0216 (10)	0.0200 (9)	−0.0009 (7)	0.0019 (7)	−0.0011 (8)
C3	0.0287 (11)	0.0323 (12)	0.0186 (9)	−0.0090 (9)	0.0009 (8)	−0.0010 (9)
C4	0.0278 (11)	0.0587 (17)	0.0320 (11)	−0.0065 (11)	−0.0045 (9)	−0.0122 (12)
C5	0.0167 (8)	0.0205 (10)	0.0191 (8)	0.0016 (7)	0.0028 (7)	0.0000 (8)
C6	0.0178 (9)	0.0252 (10)	0.0183 (9)	0.0000 (8)	0.0035 (7)	0.0013 (8)
C7	0.0201 (9)	0.0234 (10)	0.0191 (9)	−0.0024 (8)	0.0031 (7)	−0.0005 (8)
C8	0.0176 (8)	0.0233 (10)	0.0196 (9)	−0.0055 (7)	0.0038 (7)	−0.0007 (8)
C9	0.0194 (9)	0.0253 (10)	0.0185 (9)	−0.0047 (8)	0.0021 (7)	0.0011 (8)
C10	0.0206 (9)	0.0243 (11)	0.0281 (10)	−0.0030 (8)	−0.0001 (8)	−0.0005 (9)
C11	0.0211 (9)	0.0309 (12)	0.0286 (10)	−0.0014 (8)	0.0069 (8)	−0.0041 (9)
C12	0.0213 (9)	0.0336 (12)	0.0186 (9)	−0.0064 (9)	0.0038 (7)	−0.0019 (9)
C13	0.0211 (9)	0.0286 (11)	0.0191 (9)	−0.0024 (8)	0.0010 (7)	0.0042 (8)
C14	0.0253 (10)	0.0321 (12)	0.0405 (12)	0.0011 (9)	0.0010 (9)	0.0029 (11)
C15	0.0292 (10)	0.0508 (15)	0.0210 (10)	−0.0065 (10)	0.0078 (8)	−0.0011 (10)
C16	0.0200 (9)	0.0281 (11)	0.0156 (8)	−0.0024 (8)	0.0022 (7)	−0.0029 (8)
C17	0.0177 (9)	0.0481 (14)	0.0235 (10)	−0.0014 (9)	0.0032 (7)	−0.0040 (10)
C18	0.0258 (10)	0.0389 (13)	0.0301 (11)	0.0067 (9)	−0.0033 (8)	−0.0086 (10)
C19	0.0248 (19)	0.0451 (15)	0.0237 (10)	−0.0112 (13)	−0.0055 (10)	0.0059 (10)
C20	0.040 (4)	0.0552 (19)	0.032 (3)	−0.001 (2)	−0.012 (3)	0.009 (2)
C21	0.039 (4)	0.063 (2)	0.038 (4)	0.002 (3)	−0.013 (2)	0.009 (3)
C22	0.030 (3)	0.058 (4)	0.0265 (18)	−0.013 (3)	−0.008 (2)	0.012 (2)
C23	0.042 (3)	0.059 (5)	0.0179 (14)	−0.010 (3)	−0.0079 (14)	0.011 (2)
C24	0.0328 (18)	0.062 (4)	0.0146 (19)	−0.0076 (19)	−0.0034 (13)	0.006 (2)
C19'	0.0248 (19)	0.0451 (15)	0.0237 (10)	−0.0112 (13)	−0.0055 (10)	0.0059 (10)
C20'	0.040 (4)	0.0552 (19)	0.032 (3)	−0.001 (2)	−0.012 (3)	0.009 (2)
C21'	0.039 (4)	0.063 (2)	0.038 (4)	0.002 (3)	−0.013 (2)	0.009 (3)
C22'	0.030 (3)	0.058 (4)	0.0265 (18)	−0.013 (3)	−0.008 (2)	0.012 (2)
C23'	0.042 (3)	0.059 (5)	0.0179 (14)	−0.010 (3)	−0.0079 (14)	0.011 (2)
C24'	0.0328 (18)	0.062 (4)	0.0146 (19)	−0.0076 (19)	−0.0034 (13)	0.006 (2)

Geometric parameters (Å, º) top

N1—C6	1.366 (2)	C13—H13	0.9500
N1—C1	1.388 (2)	C14—H14A	0.9800
N1—H1	0.92 (3)	C14—H14B	0.9800
N2—C6	1.380 (2)	C14—H14C	0.9800
N2—C5	1.406 (2)	C15—H15A	0.9800
N2—C16	1.479 (2)	C15—H15B	0.9800
O1—C1	1.224 (2)	C15—H15C	0.9800
O2—C6	1.230 (2)	C16—H16A	0.9900
O3—C16	1.396 (2)	C16—H16B	0.9900
O3—C17	1.439 (2)	C17—C18	1.488 (3)
O4—C19	1.352 (6)	C17—H17A	0.9900
O4—C19'	1.395 (6)	C17—H17B	0.9900
O4—C18	1.429 (2)	C18—H18A	0.9900
C1—C2	1.459 (2)	C18—H18B	0.9900
C2—C5	1.352 (2)	C19—C20	1.3900
C2—C3	1.506 (3)	C19—C24	1.3900
C3—C4	1.525 (3)	C20—C21	1.3900
C3—H3A	0.9900	C20—H20	0.9500
C3—H3B	0.9900	C21—C22	1.3900
C4—H4A	0.9800	C21—H21	0.9500
C4—H4B	0.9800	C22—C23	1.3900
C4—H4C	0.9800	C22—H22	0.9500
C5—C7	1.508 (2)	C23—C24	1.3900
C7—C8	1.522 (2)	C23—H23	0.9500
C7—H7A	0.9900	C24—H24	0.9500
C7—H7B	0.9900	C19'—C20'	1.3900
C8—C9	1.392 (3)	C19'—C24'	1.3900
C8—C13	1.393 (2)	C20'—C21'	1.3900
C9—C10	1.388 (3)	C20'—H20'	0.9500
C9—H9	0.9500	C21'—C22'	1.3900
C10—C11	1.401 (3)	C21'—H21'	0.9500
C10—C14	1.504 (3)	C22'—C23'	1.3900
C11—C12	1.389 (3)	C22'—H22'	0.9500
C11—H11	0.9500	C23'—C24'	1.3900
C12—C13	1.393 (3)	C23'—H23'	0.9500
C12—C15	1.510 (2)	C24'—H24'	0.9500

C6—N1—C1	126.42 (16)	H14B—C14—H14C	109.5
C6—N1—H1	116.5 (15)	C12—C15—H15A	109.5
C1—N1—H1	117.1 (15)	C12—C15—H15B	109.5
C6—N2—C5	122.04 (15)	H15A—C15—H15B	109.5
C6—N2—C16	117.20 (15)	C12—C15—H15C	109.5
C5—N2—C16	120.70 (15)	H15A—C15—H15C	109.5
C16—O3—C17	114.49 (15)	H15B—C15—H15C	109.5
C19—O4—C18	121.0 (4)	O3—C16—N2	113.50 (15)
C19'—O4—C18	116.3 (4)	O3—C16—H16A	108.9
O1—C1—N1	119.88 (17)	N2—C16—H16A	108.9
O1—C1—C2	124.54 (18)	O3—C16—H16B	108.9
N1—C1—C2	115.58 (15)	N2—C16—H16B	108.9
C5—C2—C1	119.08 (17)	H16A—C16—H16B	107.7
C5—C2—C3	126.12 (17)	O3—C17—C18	109.48 (15)
C1—C2—C3	114.80 (16)	O3—C17—H17A	109.8
C2—C3—C4	113.85 (18)	C18—C17—H17A	109.8
C2—C3—H3A	108.8	O3—C17—H17B	109.8
C4—C3—H3A	108.8	C18—C17—H17B	109.8
C2—C3—H3B	108.8	H17A—C17—H17B	108.2
C4—C3—H3B	108.8	O4—C18—C17	107.43 (17)
H3A—C3—H3B	107.7	O4—C18—H18A	110.2
C3—C4—H4A	109.5	C17—C18—H18A	110.2
C3—C4—H4B	109.5	O4—C18—H18B	110.2
H4A—C4—H4B	109.5	C17—C18—H18B	110.2
C3—C4—H4C	109.5	H18A—C18—H18B	108.5
H4A—C4—H4C	109.5	O4—C19—C20	126.9 (6)
H4B—C4—H4C	109.5	O4—C19—C24	113.0 (6)
C2—C5—N2	121.15 (16)	C20—C19—C24	120.0
C2—C5—C7	123.20 (17)	C19—C20—C21	120.0
N2—C5—C7	115.65 (15)	C19—C20—H20	120.0
O2—C6—N1	121.52 (16)	C21—C20—H20	120.0
O2—C6—N2	122.85 (16)	C22—C21—C20	120.0
N1—C6—N2	115.63 (16)	C22—C21—H21	120.0
C5—C7—C8	115.86 (16)	C20—C21—H21	120.0
C5—C7—H7A	108.3	C23—C22—C21	120.0
C8—C7—H7A	108.3	C23—C22—H22	120.0
C5—C7—H7B	108.3	C21—C22—H22	120.0
C8—C7—H7B	108.3	C24—C23—C22	120.0
H7A—C7—H7B	107.4	C24—C23—H23	120.0
C9—C8—C13	118.74 (17)	C22—C23—H23	120.0
C9—C8—C7	122.65 (16)	C23—C24—C19	120.0
C13—C8—C7	118.53 (17)	C23—C24—H24	120.0
C10—C9—C8	121.43 (17)	C19—C24—H24	120.0
C10—C9—H9	119.3	C20'—C19'—C24'	120.0
C8—C9—H9	119.3	C20'—C19'—O4	123.3 (6)
C9—C10—C11	118.53 (18)	C24'—C19'—O4	116.7 (6)
C9—C10—C14	120.98 (17)	C19'—C20'—C21'	120.0
C11—C10—C14	120.49 (18)	C19'—C20'—H20'	120.0
C12—C11—C10	121.36 (18)	C21'—C20'—H20'	120.0
C12—C11—H11	119.3	C20'—C21'—C22'	120.0
C10—C11—H11	119.3	C20'—C21'—H21'	120.0
C11—C12—C13	118.63 (17)	C22'—C21'—H21'	120.0
C11—C12—C15	121.06 (18)	C23'—C22'—C21'	120.0
C13—C12—C15	120.30 (18)	C23'—C22'—H22'	120.0
C12—C13—C8	121.29 (18)	C21'—C22'—H22'	120.0
C12—C13—H13	119.4	C22'—C23'—C24'	120.0
C8—C13—H13	119.4	C22'—C23'—H23'	120.0
C10—C14—H14A	109.5	C24'—C23'—H23'	120.0
C10—C14—H14B	109.5	C23'—C24'—C19'	120.0
H14A—C14—H14B	109.5	C23'—C24'—H24'	120.0
C10—C14—H14C	109.5	C19'—C24'—H24'	120.0
H14A—C14—H14C	109.5

C6—N1—C1—O1	176.73 (18)	C15—C12—C13—C8	177.89 (18)
C6—N1—C1—C2	−2.7 (3)	C9—C8—C13—C12	0.6 (3)
O1—C1—C2—C5	−176.43 (18)	C7—C8—C13—C12	−176.36 (17)
N1—C1—C2—C5	3.0 (3)	C17—O3—C16—N2	75.77 (19)
O1—C1—C2—C3	3.4 (3)	C6—N2—C16—O3	−104.31 (19)
N1—C1—C2—C3	−177.20 (16)	C5—N2—C16—O3	72.9 (2)
C5—C2—C3—C4	97.0 (2)	C16—O3—C17—C18	144.73 (17)
C1—C2—C3—C4	−82.8 (2)	C19—O4—C18—C17	−170.9 (7)
C1—C2—C5—N2	−0.8 (3)	C19'—O4—C18—C17	−167.2 (6)
C3—C2—C5—N2	179.36 (17)	O3—C17—C18—O4	−64.1 (2)
C1—C2—C5—C7	179.49 (17)	C19'—O4—C19—C20	−35 (10)
C3—C2—C5—C7	−0.3 (3)	C18—O4—C19—C20	1.0 (12)
C6—N2—C5—C2	−2.0 (3)	C19'—O4—C19—C24	142 (11)
C16—N2—C5—C2	−179.04 (17)	C18—O4—C19—C24	177.9 (3)
C6—N2—C5—C7	177.74 (16)	O4—C19—C20—C21	176.7 (12)
C16—N2—C5—C7	0.7 (2)	C24—C19—C20—C21	0.0
C1—N1—C6—O2	−178.95 (17)	C19—C20—C21—C22	0.0
C1—N1—C6—N2	0.1 (3)	C20—C21—C22—C23	0.0
C5—N2—C6—O2	−178.63 (17)	C21—C22—C23—C24	0.0
C16—N2—C6—O2	−1.5 (3)	C22—C23—C24—C19	0.0
C5—N2—C6—N1	2.3 (3)	O4—C19—C24—C23	−177.1 (10)
C16—N2—C6—N1	179.49 (16)	C20—C19—C24—C23	0.0
C2—C5—C7—C8	−104.9 (2)	C19—O4—C19'—C20'	156 (11)
N2—C5—C7—C8	75.4 (2)	C18—O4—C19'—C20'	10.5 (10)
C5—C7—C8—C9	35.4 (2)	C19—O4—C19'—C24'	−25 (10)
C5—C7—C8—C13	−147.79 (18)	C18—O4—C19'—C24'	−170.5 (4)
C13—C8—C9—C10	−0.2 (3)	C24'—C19'—C20'—C21'	0.0
C7—C8—C9—C10	176.65 (18)	O4—C19'—C20'—C21'	178.9 (11)
C8—C9—C10—C11	0.4 (3)	C19'—C20'—C21'—C22'	0.0
C8—C9—C10—C14	−179.14 (17)	C20'—C21'—C22'—C23'	0.0
C9—C10—C11—C12	−1.0 (3)	C21'—C22'—C23'—C24'	0.0
C14—C10—C11—C12	178.52 (18)	C22'—C23'—C24'—C19'	0.0
C10—C11—C12—C13	1.4 (3)	C20'—C19'—C24'—C23'	0.0
C10—C11—C12—C15	−177.69 (19)	O4—C19'—C24'—C23'	−179.0 (10)
C11—C12—C13—C8	−1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.92 (3)	1.94 (3)	2.859 (2)	173 (2)

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₈N₂O₄
M_r	408.48
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	16.1116 (6), 4.8211 (2), 27.5125 (10)
β (°)	92.574 (3)
V (Å³)	2134.90 (14)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.20 × 0.10 × 0.05

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.873, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	6587, 4115, 2940
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.130, 1.03
No. of reflections	4115
No. of parameters	272
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.33

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···O2ⁱ	0.92 (3)	1.94 (3)	2.859 (2)	173 (2)

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

We thank 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
El-Brollosy, N. R., Al-Omar, M. A., Al-Deeb, O. A., El-Emam, A. A. & Nielsen, C. (2007). J. Chem. Res. pp. 263–267. Google Scholar
El-Brollosy, N. R., Sorensen, E. R., Pedersen, E. B., Sanna, G., La Colla, P. & Loddo, R. (2008). Arch. Pharm. Chem. Life Sci. 341, 9–19. 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 67| Part 11| November 2011| Page o2839

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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