6-(3,5-Dimethyl-benz-yl)-5-ethyl-1-[(2-phenyl-eth-oxy)meth-yl]pyrimidine-2,4(1H,3H)dione.

In the title pyrimidine derivative, C(24)H(28)N(2)O(3), 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-dimethyl-benzyl substituent, whereas it is nearly parallel to the benzene ring of the pheneth-oxy-methyl unit, with a dihedral angle of 8.17 (8)°. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol-ecules are linked by a pair of amide-uracil N-H⋯O hydrogen bonds into an inversion R(2) (2)(8) dimer. These dimers are stacked along the b axis through π-π inter-actions with a centroid-centroid distance of 3.9517 (8) Å. Weak C-H⋯π inter-actions 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 = 392.48

Triclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.05

3863 reflections

270 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.18 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812009841/is5086sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812009841/is5086Isup3.cml

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

C24H28N2O3	Z = 2
Mr = 392.48	F(000) = 420
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0599P)2 + 0.2589P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
3863 reflections	Δρmax = 0.27 e Å−3
270 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .