6-(3,5-Dimethyl­benz­yl)-5-ethyl-1-[(2-phenyl­eth­oxy)meth­yl]pyrimidine-2,4(1H,3H)dione

El-Brollosy, N.R.; Attia, M.I.; Ghabbour, H.A.; Chantrapromma, S.; Fun, H.-K.

doi:10.1107/S1600536812009841

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages o1031-o1032

doi:10.1107/S1600536812009841

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6-(3,5-Dimethylbenzyl)-5-ethyl-1-[(2-phenylethoxy)methyl]pyrimidine-2,4(1H,3H)dione

Nasser R. El-Brollosy,^a Mohamed I. Attia,^a Hazem A. Ghabbour,^a Suchada Chantrapromma ^b ‡ and Hoong-Kun Fun ^c ^*§

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia, ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and ^cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
^*Correspondence e-mail: hkfun@usm.my

(Received 29 February 2012; accepted 6 March 2012; online 10 March 2012)

In the title pyrimidine derivative, C₂₄H₂₈N₂O₃, the uracil unit is essentially planar with an r.m.s. deviation of 0.0054 (1) Å for the eight non-H atoms. The pyrimidine ring is tilted by a dihedral angle of 77.08 (7)° with respect to the aromatic ring of the 3,5-dimethylbenzyl substituent, whereas it is nearly parallel to the benzene ring of the phenethoxymethyl unit, with a dihedral angle of 8.17 (8)°. An intramolecular C—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by a pair of amide–uracil N—H⋯O hydrogen bonds into an inversion R₂²(8) dimer. These dimers are stacked along the b axis through π–π interactions with a centroid–centroid distance of 3.9517 (8) Å. Weak C—H⋯π interactions are also present.

Related literature

For bond-length data, see: Allen et al. (1987 ). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ). For background to anti-viral HIV therapies, see: El-Brollosy et al. (2007 , 2008 , 2009 ); Hopkins et al. (1996 , 1999 ). For related structures, see: El-Brollosy et al. (2011 , 2012 ).

Experimental

Crystal data

C₂₄H₂₈N₂O₃
M_r = 392.48
Triclinic, $[P \overline 1]$
a = 8.34310 (1) Å
b = 8.47760 (1) Å
c = 15.9821 (2) Å
α = 91.5660 (1)°
β = 91.7820 (1)°
γ = 109.8350 (1)°
V = 1061.97 (1) Å³
Z = 2
Cu Kα radiation
μ = 0.65 mm⁻¹
T = 296 K
0.58 × 0.40 × 0.31 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.705, T_max = 0.824
13575 measured reflections
3863 independent reflections
3542 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.123
S = 1.05
3863 reflections
270 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C15–C20 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1ⁱ	0.889 (18)	1.969 (18)	2.8558 (15)	175.7 (17)
C14—H14B⋯O3	0.97	2.36	3.0349 (18)	126
C21—H21B⋯Cg3ⁱⁱ	0.96	2.90	3.845 (3)	170
C22—H22C⋯Cg3ⁱⁱⁱ	0.96	2.92	3.861 (3)	166
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y, -z+1; (iii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812009841/is5086sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812009841/is5086Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812009841/is5086Isup3.cml

checkCIF report

Comment top

Non-nucleoside reverse transcriptase inhibitors (NNRTIs) are very promising therapies in the treatment of human immunodeficiency virus (HIV) (Hopkins et al., 1996, 1999). In continuation to our interest in NNRTIs (El-Brollosy et al., 2007, 2008, 2009), and as part of on-going structural studies of pyrimidine derivatives (El-Brollosy et al., 2011), we synthesized the title compound (I) as a potential non-nucleoside reverse transcriptase inhibitor. It showed a good antiviral activity against HIV-1 (El-Brollosy et al., 2009). Herein, the crystal structure of (I) was reported.

In the title pyrimidine derivative, C₂₄H₂₈N₂O₃, the uracil unit is essentialy planar with an r.m.s. deviation of 0.0054 (1) Å for the eight non-H atoms (C1–C4/N1/N2/O1/O2). The 3,5-dimethylbenzyl unit is also planar with an r.m.s. deviation of 0.0049 (2) Å for the nine non-H atoms (C14–C22). The pyrimidine ring is tilted with the aromatic ring (C15–C20) of the 3,5-dimethylbenzyl substituent by a dihedral angle of 77.08 (7)°, whereas nearly parallel to the C8–C13 benzene ring of the phenylethoxymethyl unit with a dihedral angle of 8.17 (7)°. The dihedral angle between the two benzene rings (C8–C13 and C15–C20) is 82.14 (8)°. The orientation of the ethyl and phenethoxymethyl groups respected to the uracil can be indicated by the torsion angles C1–C2–C23–C24 = -85.87 (19)°, and C6–O3–C5–N1 = -67.31 (14)° and C5–O3–C6–C7 = 159.11 (12)°. Intramolecular weak C14—H14B···O3 interaction generates an S(6) ring motif (Fig. 1) (Bernstein et al., 1995). The bond distances in (I) are within normal ranges (Allen et al., 1987) and comparable to the related structures (El-Brollosy et al., 2011, 2012).

In the crystal packing, (Fig. 2), the two molecules are linked by a pair of N2—H1N2···O1 hydrogen bonds (Table 1) into a centrosymmetric R²₂(8) dimer (Bernstein et al., 1995). These dimers are stacked along the b axis (Fig. 2) through π–π interactions with a Cg1···Cg2^{iv, v} distance of 3.9517 (8) Å [symmetry codes: (iv) x, -1+y, z; (v) x, 1+y, z]. Weak C—H···π interactions (Table 1) are also present.

Related literature top

For bond-length data, see: Allen et al. (1987). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For background to anti-viral HIV therapies, see: El-Brollosy et al. (2007, 2008, 2009); Hopkins et al. (1996, 1999). For related structures, see: El-Brollosy et al. (2011, 2012).

Experimental top

5-Ethyl-6-(3,5-dimethylbenzyl)uracil (0.258 g, 1 mmol) was stirred in anhydrous CH₃CN (15 ml) under nitrogen and N,O-bis(trimethylsilyl)acetamide (0.87 ml, 3.5 mol) was added. After a clear solution was obtained (10 min), the reaction mixture was cooled to 223 K and trimethylsilyl trifluoromethanesulphonate (0.18 ml, 1 mmol) was added followed by dropwise addition of bis-(2-phenylethyloxy)methane (0.512 g, 2 mmol). The mixture was stirred at room temperature for 4 hr. The reaction was quenched with saturated aqueous NaHCO₃ solution (5 ml) and evaporated under reduced pressure. The residue was extracted with ether (3 × 50 ml), the combined organic fractions were collected, dried (MgSO₄) and evaporated under reduced pressure. The residue was chromatographed on silica gel column with CHCl₃ to afford a white solid, which was recrystallized from ethanol to obtain the title compound as colorless crystals. Yield: 201 mg (51 %), M.p.: 396–398 K.

Structure description top

For bond-length data, see: Allen et al. (1987). For details of hydrogen-bond motifs, see: Bernstein et al. (1995). For background to anti-viral HIV therapies, see: El-Brollosy et al. (2007, 2008, 2009); Hopkins et al. (1996, 1999). For related structures, see: El-Brollosy et al. (2011, 2012).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Only the non-aromatic benzyl H and amide H atoms were shown for clarify.
	Fig. 2. The crystal packing diagram of the title compound, viewed along the b axis. Only H atoms involving in intermolecular hydrogen bonds are drawn for clarify. N—H···O hydrogen bonds are shown as dashed lines.

6-(3,5-Dimethylbenzyl)-5-ethyl-1-[(2-phenylethoxy)methyl]pyrimidine- 2,4(1H,3H)dione top

Crystal data top

C₂₄H₂₈N₂O₃	Z = 2
M_r = 392.48	F(000) = 420
Triclinic, P1	D_x = 1.227 Mg m⁻³
Hall symbol: -P 1	Melting point = 396–398 K
a = 8.34310 (1) Å	Cu Kα radiation, λ = 1.54178 Å
b = 8.47760 (1) Å	Cell parameters from 3863 reflections
c = 15.9821 (2) Å	θ = 2.8–70.0°
α = 91.5660 (1)°	µ = 0.65 mm⁻¹
β = 91.7820 (1)°	T = 296 K
γ = 109.8350 (1)°	Block, colorless
V = 1061.97 (1) Å³	0.58 × 0.40 × 0.31 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3863 independent reflections
Radiation source: sealed tube	3542 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
φ and ω scans	θ_max = 70.0°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.705, T_max = 0.824	k = −10→10
13575 measured reflections	l = −19→19

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.123	w = 1/[σ²(F_o²) + (0.0599P)² + 0.2589P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.001
3863 reflections	Δρ_max = 0.27 e Å⁻³
270 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0158 (11)

Crystal data top

C₂₄H₂₈N₂O₃	γ = 109.8350 (1)°
M_r = 392.48	V = 1061.97 (1) Å³
Triclinic, P1	Z = 2
a = 8.34310 (1) Å	Cu Kα radiation
b = 8.47760 (1) Å	µ = 0.65 mm⁻¹
c = 15.9821 (2) Å	T = 296 K
α = 91.5660 (1)°	0.58 × 0.40 × 0.31 mm
β = 91.7820 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3863 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3542 reflections with I > 2σ(I)
T_min = 0.705, T_max = 0.824	R_int = 0.022
13575 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.123	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.27 e Å⁻³
3863 reflections	Δρ_min = −0.18 e Å⁻³
270 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

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

	x	y	z	U_iso*/U_eq
N1	0.73374 (14)	0.17782 (14)	0.18049 (7)	0.0389 (3)
N2	0.86631 (15)	0.35816 (15)	0.07678 (7)	0.0416 (3)
H1N2	0.855 (2)	0.413 (2)	0.0316 (12)	0.050 (4)*
O1	1.15299 (13)	0.46537 (13)	0.07074 (6)	0.0516 (3)
O2	0.57921 (14)	0.25880 (15)	0.08011 (7)	0.0586 (3)
O3	0.56324 (12)	−0.10907 (12)	0.19600 (6)	0.0465 (3)
C1	0.89379 (17)	0.18893 (16)	0.21512 (8)	0.0372 (3)
C2	1.03943 (17)	0.28209 (17)	0.18009 (8)	0.0398 (3)
C3	1.02860 (18)	0.37579 (17)	0.10647 (8)	0.0400 (3)
C4	0.71675 (18)	0.26506 (17)	0.11021 (8)	0.0408 (3)
C5	0.57628 (17)	0.05835 (18)	0.21083 (9)	0.0439 (3)
H5A	0.5718	0.0791	0.2706	0.053*
H5B	0.4793	0.0771	0.1835	0.053*
C6	0.5432 (2)	−0.1640 (2)	0.10923 (9)	0.0496 (4)
H6A	0.6137	−0.0757	0.0755	0.060*
H6B	0.4253	−0.1918	0.0897	0.060*
C7	0.5968 (2)	−0.3174 (2)	0.10163 (11)	0.0545 (4)
H7A	0.5223	−0.4062	0.1337	0.065*
H7B	0.5846	−0.3567	0.0434	0.065*
C8	0.77867 (19)	−0.27984 (17)	0.13271 (9)	0.0457 (3)
C9	0.8179 (2)	−0.33678 (19)	0.20831 (10)	0.0511 (4)
H9A	0.7302	−0.4020	0.2402	0.061*
C10	0.9850 (2)	−0.2985 (2)	0.23730 (11)	0.0561 (4)
H10A	1.0087	−0.3380	0.2883	0.067*
C11	1.1160 (2)	−0.2024 (2)	0.19109 (12)	0.0579 (4)
H11A	1.2285	−0.1770	0.2105	0.070*
C12	1.0798 (2)	−0.1441 (2)	0.11607 (12)	0.0614 (4)
H12A	1.1682	−0.0782	0.0847	0.074*
C13	0.9130 (2)	−0.1827 (2)	0.08704 (10)	0.0545 (4)
H13A	0.8901	−0.1430	0.0360	0.065*
C14	0.89232 (19)	0.09042 (18)	0.29230 (8)	0.0430 (3)
H14A	1.0062	0.0871	0.3029	0.052*
H14B	0.8170	−0.0241	0.2806	0.052*
C15	0.83675 (18)	0.15601 (18)	0.37173 (8)	0.0433 (3)
C16	0.8249 (2)	0.31421 (19)	0.38003 (9)	0.0491 (4)
H16A	0.8513	0.3851	0.3353	0.059*
C17	0.7738 (2)	0.3697 (2)	0.45442 (10)	0.0573 (4)
C18	0.7354 (2)	0.2618 (3)	0.52015 (10)	0.0642 (5)
H18A	0.7011	0.2972	0.5699	0.077*
C19	0.7467 (2)	0.1027 (2)	0.51394 (9)	0.0597 (4)
C20	0.7976 (2)	0.0516 (2)	0.43944 (9)	0.0523 (4)
H20A	0.8059	−0.0549	0.4344	0.063*
C21	0.7013 (3)	−0.0151 (3)	0.58581 (12)	0.0859 (7)
H21A	0.7585	−0.0957	0.5808	0.129*
H21B	0.5802	−0.0724	0.5842	0.129*
H21C	0.7364	0.0481	0.6380	0.129*
C22	0.7617 (3)	0.5431 (3)	0.46177 (14)	0.0814 (6)
H22A	0.6780	0.5439	0.5015	0.122*
H22B	0.7287	0.5734	0.4081	0.122*
H22C	0.8705	0.6222	0.4803	0.122*
C23	1.21678 (19)	0.2957 (2)	0.21143 (10)	0.0509 (4)
H23A	1.2136	0.1883	0.2322	0.061*
H23B	1.2922	0.3205	0.1649	0.061*
C24	1.2888 (3)	0.4295 (3)	0.28019 (13)	0.0758 (5)
H24A	1.3994	0.4298	0.2989	0.114*
H24B	1.2142	0.4065	0.3263	0.114*
H24C	1.2987	0.5372	0.2591	0.114*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0382 (6)	0.0428 (6)	0.0351 (5)	0.0130 (5)	0.0022 (4)	0.0040 (4)
N2	0.0461 (6)	0.0448 (6)	0.0340 (6)	0.0152 (5)	0.0002 (5)	0.0083 (5)
O1	0.0464 (6)	0.0569 (6)	0.0462 (6)	0.0096 (5)	0.0055 (4)	0.0146 (5)
O2	0.0461 (6)	0.0739 (8)	0.0567 (7)	0.0212 (5)	−0.0057 (5)	0.0165 (5)
O3	0.0450 (5)	0.0460 (5)	0.0447 (5)	0.0105 (4)	0.0018 (4)	0.0049 (4)
C1	0.0413 (7)	0.0390 (7)	0.0321 (6)	0.0148 (6)	−0.0005 (5)	−0.0003 (5)
C2	0.0419 (7)	0.0420 (7)	0.0349 (6)	0.0133 (6)	0.0006 (5)	0.0021 (5)
C3	0.0442 (7)	0.0393 (7)	0.0346 (6)	0.0120 (6)	0.0025 (5)	0.0006 (5)
C4	0.0435 (7)	0.0438 (7)	0.0364 (6)	0.0165 (6)	−0.0012 (5)	0.0019 (5)
C5	0.0387 (7)	0.0503 (8)	0.0418 (7)	0.0135 (6)	0.0060 (5)	0.0033 (6)
C6	0.0455 (8)	0.0550 (9)	0.0478 (8)	0.0177 (7)	−0.0073 (6)	−0.0035 (6)
C7	0.0501 (9)	0.0463 (8)	0.0630 (9)	0.0129 (7)	−0.0099 (7)	−0.0063 (7)
C8	0.0472 (8)	0.0377 (7)	0.0527 (8)	0.0161 (6)	−0.0016 (6)	−0.0064 (6)
C9	0.0487 (8)	0.0435 (8)	0.0588 (9)	0.0122 (7)	0.0035 (7)	0.0046 (6)
C10	0.0566 (9)	0.0526 (9)	0.0604 (9)	0.0208 (8)	−0.0064 (7)	0.0038 (7)
C11	0.0437 (8)	0.0571 (9)	0.0740 (11)	0.0190 (7)	−0.0016 (7)	−0.0018 (8)
C12	0.0506 (9)	0.0626 (10)	0.0719 (11)	0.0190 (8)	0.0167 (8)	0.0082 (8)
C13	0.0589 (9)	0.0562 (9)	0.0520 (9)	0.0240 (8)	0.0054 (7)	0.0045 (7)
C14	0.0465 (7)	0.0439 (7)	0.0388 (7)	0.0153 (6)	0.0008 (5)	0.0076 (5)
C15	0.0442 (7)	0.0470 (8)	0.0339 (7)	0.0093 (6)	−0.0027 (5)	0.0054 (5)
C16	0.0574 (9)	0.0488 (8)	0.0370 (7)	0.0127 (7)	0.0015 (6)	0.0039 (6)
C17	0.0604 (10)	0.0636 (10)	0.0446 (8)	0.0177 (8)	−0.0007 (7)	−0.0067 (7)
C18	0.0635 (10)	0.0863 (13)	0.0354 (8)	0.0165 (9)	0.0033 (7)	−0.0063 (7)
C19	0.0591 (9)	0.0743 (11)	0.0346 (7)	0.0082 (8)	−0.0019 (6)	0.0100 (7)
C20	0.0575 (9)	0.0543 (9)	0.0394 (7)	0.0113 (7)	−0.0019 (6)	0.0115 (6)
C21	0.0950 (15)	0.1073 (17)	0.0425 (9)	0.0158 (13)	0.0066 (9)	0.0258 (10)
C22	0.1037 (16)	0.0772 (13)	0.0676 (12)	0.0374 (12)	0.0066 (11)	−0.0150 (10)
C23	0.0451 (8)	0.0563 (9)	0.0510 (8)	0.0163 (7)	0.0024 (6)	0.0109 (7)
C24	0.0590 (11)	0.0903 (14)	0.0677 (11)	0.0142 (10)	−0.0150 (9)	−0.0076 (10)

Geometric parameters (Å, º) top

N1—C4	1.3913 (17)	C12—C13	1.379 (2)
N1—C1	1.4014 (17)	C12—H12A	0.9300
N1—C5	1.4664 (17)	C13—H13A	0.9300
N2—C4	1.3643 (18)	C14—C15	1.519 (2)
N2—C3	1.3783 (18)	C14—H14A	0.9700
N2—H1N2	0.887 (19)	C14—H14B	0.9700
O1—C3	1.2270 (17)	C15—C16	1.381 (2)
O2—C4	1.2141 (17)	C15—C20	1.3926 (19)
O3—C5	1.3992 (17)	C16—C17	1.398 (2)
O3—C6	1.4372 (18)	C16—H16A	0.9300
C1—C2	1.3524 (19)	C17—C18	1.385 (3)
C1—C14	1.5065 (17)	C17—C22	1.509 (3)
C2—C3	1.4548 (18)	C18—C19	1.385 (3)
C2—C23	1.5128 (19)	C18—H18A	0.9300
C5—H5A	0.9700	C19—C20	1.383 (2)
C5—H5B	0.9700	C19—C21	1.514 (2)
C6—C7	1.514 (2)	C20—H20A	0.9300
C6—H6A	0.9700	C21—H21A	0.9600
C6—H6B	0.9700	C21—H21B	0.9600
C7—C8	1.505 (2)	C21—H21C	0.9600
C7—H7A	0.9700	C22—H22A	0.9600
C7—H7B	0.9700	C22—H22B	0.9600
C8—C9	1.384 (2)	C22—H22C	0.9600
C8—C13	1.387 (2)	C23—C24	1.511 (3)
C9—C10	1.381 (2)	C23—H23A	0.9700
C9—H9A	0.9300	C23—H23B	0.9700
C10—C11	1.372 (2)	C24—H24A	0.9600
C10—H10A	0.9300	C24—H24B	0.9600
C11—C12	1.373 (3)	C24—H24C	0.9600
C11—H11A	0.9300

C4—N1—C1	121.92 (11)	C12—C13—C8	121.12 (15)
C4—N1—C5	116.53 (11)	C12—C13—H13A	119.4
C1—N1—C5	121.18 (11)	C8—C13—H13A	119.4
C4—N2—C3	126.71 (11)	C1—C14—C15	116.09 (11)
C4—N2—H1N2	115.1 (11)	C1—C14—H14A	108.3
C3—N2—H1N2	118.2 (11)	C15—C14—H14A	108.3
C5—O3—C6	114.94 (11)	C1—C14—H14B	108.3
C2—C1—N1	121.22 (12)	C15—C14—H14B	108.3
C2—C1—C14	122.80 (12)	H14A—C14—H14B	107.4
N1—C1—C14	115.98 (11)	C16—C15—C20	118.73 (14)
C1—C2—C3	118.98 (12)	C16—C15—C14	123.13 (12)
C1—C2—C23	124.62 (12)	C20—C15—C14	118.14 (13)
C3—C2—C23	116.39 (12)	C15—C16—C17	121.23 (14)
O1—C3—N2	120.07 (12)	C15—C16—H16A	119.4
O1—C3—C2	123.99 (13)	C17—C16—H16A	119.4
N2—C3—C2	115.93 (12)	C18—C17—C16	118.24 (16)
O2—C4—N2	122.00 (12)	C18—C17—C22	121.61 (16)
O2—C4—N1	122.80 (13)	C16—C17—C22	120.15 (16)
N2—C4—N1	115.20 (11)	C17—C18—C19	121.94 (15)
O3—C5—N1	112.94 (11)	C17—C18—H18A	119.0
O3—C5—H5A	109.0	C19—C18—H18A	119.0
N1—C5—H5A	109.0	C20—C19—C18	118.37 (15)
O3—C5—H5B	109.0	C20—C19—C21	120.28 (18)
N1—C5—H5B	109.0	C18—C19—C21	121.34 (17)
H5A—C5—H5B	107.8	C19—C20—C15	121.50 (16)
O3—C6—C7	107.77 (12)	C19—C20—H20A	119.3
O3—C6—H6A	110.2	C15—C20—H20A	119.3
C7—C6—H6A	110.2	C19—C21—H21A	109.5
O3—C6—H6B	110.2	C19—C21—H21B	109.5
C7—C6—H6B	110.2	H21A—C21—H21B	109.5
H6A—C6—H6B	108.5	C19—C21—H21C	109.5
C8—C7—C6	111.71 (12)	H21A—C21—H21C	109.5
C8—C7—H7A	109.3	H21B—C21—H21C	109.5
C6—C7—H7A	109.3	C17—C22—H22A	109.5
C8—C7—H7B	109.3	C17—C22—H22B	109.5
C6—C7—H7B	109.3	H22A—C22—H22B	109.5
H7A—C7—H7B	107.9	C17—C22—H22C	109.5
C9—C8—C13	117.69 (14)	H22A—C22—H22C	109.5
C9—C8—C7	121.57 (14)	H22B—C22—H22C	109.5
C13—C8—C7	120.71 (14)	C24—C23—C2	113.15 (14)
C10—C9—C8	121.20 (15)	C24—C23—H23A	108.9
C10—C9—H9A	119.4	C2—C23—H23A	108.9
C8—C9—H9A	119.4	C24—C23—H23B	108.9
C11—C10—C9	120.18 (15)	C2—C23—H23B	108.9
C11—C10—H10A	119.9	H23A—C23—H23B	107.8
C9—C10—H10A	119.9	C23—C24—H24A	109.5
C10—C11—C12	119.56 (15)	C23—C24—H24B	109.5
C10—C11—H11A	120.2	H24A—C24—H24B	109.5
C12—C11—H11A	120.2	C23—C24—H24C	109.5
C11—C12—C13	120.24 (16)	H24A—C24—H24C	109.5
C11—C12—H12A	119.9	H24B—C24—H24C	109.5
C13—C12—H12A	119.9

C4—N1—C1—C2	−1.78 (19)	C13—C8—C9—C10	−0.1 (2)
C5—N1—C1—C2	170.99 (12)	C7—C8—C9—C10	−178.47 (14)
C4—N1—C1—C14	178.71 (12)	C8—C9—C10—C11	0.0 (2)
C5—N1—C1—C14	−8.52 (17)	C9—C10—C11—C12	0.3 (3)
N1—C1—C2—C3	1.72 (19)	C10—C11—C12—C13	−0.4 (3)
C14—C1—C2—C3	−178.80 (12)	C11—C12—C13—C8	0.4 (3)
N1—C1—C2—C23	−177.60 (12)	C9—C8—C13—C12	−0.1 (2)
C14—C1—C2—C23	1.9 (2)	C7—C8—C13—C12	178.30 (14)
C4—N2—C3—O1	−179.20 (13)	C2—C1—C14—C15	109.79 (15)
C4—N2—C3—C2	1.31 (19)	N1—C1—C14—C15	−70.71 (16)
C1—C2—C3—O1	179.10 (13)	C1—C14—C15—C16	−14.3 (2)
C23—C2—C3—O1	−1.5 (2)	C1—C14—C15—C20	166.30 (13)
C1—C2—C3—N2	−1.44 (18)	C20—C15—C16—C17	−0.3 (2)
C23—C2—C3—N2	177.93 (12)	C14—C15—C16—C17	−179.73 (14)
C3—N2—C4—O2	179.05 (13)	C15—C16—C17—C18	0.1 (3)
C3—N2—C4—N1	−1.3 (2)	C15—C16—C17—C22	−179.92 (16)
C1—N1—C4—O2	−178.91 (13)	C16—C17—C18—C19	0.2 (3)
C5—N1—C4—O2	8.0 (2)	C22—C17—C18—C19	−179.82 (18)
C1—N1—C4—N2	1.45 (18)	C17—C18—C19—C20	−0.2 (3)
C5—N1—C4—N2	−171.63 (11)	C17—C18—C19—C21	−178.89 (18)
C6—O3—C5—N1	−67.31 (14)	C18—C19—C20—C15	−0.1 (3)
C4—N1—C5—O3	108.67 (13)	C21—C19—C20—C15	178.66 (16)
C1—N1—C5—O3	−64.47 (16)	C16—C15—C20—C19	0.3 (2)
C5—O3—C6—C7	159.11 (12)	C14—C15—C20—C19	179.75 (14)
O3—C6—C7—C8	−58.84 (17)	C1—C2—C23—C24	−85.87 (19)
C6—C7—C8—C9	106.27 (16)	C3—C2—C23—C24	94.80 (17)
C6—C7—C8—C13	−72.06 (19)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.889 (18)	1.969 (18)	2.8558 (15)	175.7 (17)
C14—H14B···O3	0.97	2.36	3.0349 (18)	126
C21—H21B···Cg3ⁱⁱ	0.96	2.90	3.845 (3)	170
C22—H22C···Cg3ⁱⁱⁱ	0.96	2.92	3.861 (3)	166

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y, −z+1; (iii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₈N₂O₃
M_r	392.48
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.34310 (1), 8.47760 (1), 15.9821 (2)
α, β, γ (°)	91.5660 (1), 91.7820 (1), 109.8350 (1)
V (Å³)	1061.97 (1)
Z	2
Radiation type	Cu Kα
µ (mm⁻¹)	0.65
Crystal size (mm)	0.58 × 0.40 × 0.31

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.705, 0.824
No. of measured, independent and observed [I > 2σ(I)] reflections	13575, 3863, 3542
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.123, 1.05
No. of reflections	3863
No. of parameters	270
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.18

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C15–C20 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1ⁱ	0.889 (18)	1.969 (18)	2.8558 (15)	175.7 (17)
C14—H14B···O3	0.97	2.36	3.0349 (18)	126
C21—H21B···Cg3ⁱⁱ	0.96	2.90	3.845 (3)	170
C22—H22C···Cg3ⁱⁱⁱ	0.96	2.92	3.861 (3)	166

Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y, −z+1; (iii) −x+2, −y+1, −z+1.

Footnotes

‡Thomson Reuters ResearcherID: A-5085-2009.

§College of Pharmacy (Visiting Professor), King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia. Thomson Reuters ResearcherID: A-3561-2009.

Acknowledgements

The financial support of the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, Riyadh, Saudia Arabia, is greatly appreciated. HKF and SC thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks the King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CSD CrossRef Web of Science Google Scholar
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Hopkins, A. L., Ren, J., Esnouf, R. M., Willcox, B. E., Jones, E. Y., Ross, C., Miyasaka, T., Walker, R. T., Tanaka, H., Stammers, D. K. & Stuart, D. I. (1996). J. Med. Chem. 39, 1589–1600. CrossRef CAS PubMed Web of Science Google Scholar
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Volume 68| Part 4| April 2012| Pages o1031-o1032

doi:10.1107/S1600536812009841

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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-phenyl­eth­­oxy)meth­yl]pyrimidine-2,4(1H,3H)dione

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

6-(3,5-Dimethylbenzyl)-5-ethyl-1-[(2-phenylethoxy)methyl]pyrimidine-2,4(1H,3H)dione