6-(3,5-Dimethyl­benz­yl)-5-ethyl-1-[(3-phenyl­prop­oxy)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/S1600536811055723

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o316

doi:10.1107/S1600536811055723

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6-(3,5-Dimethylbenzyl)-5-ethyl-1-[(3-phenylpropoxy)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, 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 of the title compound, C₂₅H₃₀N₂O₃, is approximately planar (r.m.s. deviation = 0.003 Å); the C atom at the 5-position deviates by 0.012 (3) Å from the mean plane and the C atom at the 6-position by 0.038 (3) Å. In the molecule, the pyrimidine ring is oriented at 86.72 (9) and 59.75 (9)° with respect to the two benzene rings, and the two benzene rings are inclined to each other at 58.35 (9)°. In the crystal, the amino group is hydrogen-bond donor to the exocyclic O atom at the 4-position of an adjacent molecule, the hydrogen bond generating an inversion dimer.

Related literature

For the applications and synthesis of the title compound, see: El-Brollosy et al. (2009 ).

Experimental

Crystal data

C₂₅H₃₀N₂O₃
M_r = 406.51
Triclinic, $[P \overline 1]$
a = 4.8276 (4) Å
b = 14.9398 (10) Å
c = 15.4574 (12) Å
α = 76.949 (6)°
β = 89.296 (6)°
γ = 88.267 (6)°
V = 1085.53 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.980, T_max = 0.996
7623 measured reflections
4974 independent reflections
3719 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.167
S = 1.04
4974 reflections
277 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.89 (1)	1.94 (1)	2.826 (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/S1600536811055723/xu5425sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055723/xu5425Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055723/xu5425Isup3.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 planar; the C atom at the 5-position deviates by 0.012 (3) Å from the mean plane and the C atom at the 6-position by 0.038 (3) Å (Fig. 1). The amino group is hydrogen-bond donor to the exocyclic O atom at the 4-position, the hydrogen bond generating a centrosymmetric dimer (Table 1, Fig. 1).

Related literature top

For the applications and synthesis of the title compound, see: El-Brollosy et al. (2009).

Experimental top

The compound 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 C₂₅H₃₀N₂O₃ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Dimeric hydrogen-bonded structure.

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

Crystal data top

C₂₅H₃₀N₂O₃	Z = 2
M_r = 406.51	F(000) = 436
Triclinic, P1	D_x = 1.244 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8276 (4) Å	Cell parameters from 2909 reflections
b = 14.9398 (10) Å	θ = 2.7–27.5°
c = 15.4574 (12) Å	µ = 0.08 mm⁻¹
α = 76.949 (6)°	T = 100 K
β = 89.296 (6)°	Prism, colorless
γ = 88.267 (6)°	0.25 × 0.20 × 0.05 mm
V = 1085.53 (14) Å³

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4974 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	3719 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.039
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.6°, θ_min = 2.7°
ω scan	h = −6→4
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −19→19
T_min = 0.980, T_max = 0.996	l = −20→18
7623 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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0802P)² + 0.2053P] where P = (F_o² + 2F_c²)/3
4974 reflections	(Δ/σ)_max = 0.001
277 parameters	Δρ_max = 0.39 e Å⁻³
1 restraint	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₅H₃₀N₂O₃	γ = 88.267 (6)°
M_r = 406.51	V = 1085.53 (14) Å³
Triclinic, P1	Z = 2
a = 4.8276 (4) Å	Mo Kα radiation
b = 14.9398 (10) Å	µ = 0.08 mm⁻¹
c = 15.4574 (12) Å	T = 100 K
α = 76.949 (6)°	0.25 × 0.20 × 0.05 mm
β = 89.296 (6)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	4974 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	3719 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.996	R_int = 0.039
7623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	1 restraint
wR(F²) = 0.167	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.39 e Å⁻³
4974 reflections	Δρ_min = −0.29 e Å⁻³
277 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.7285 (3)	0.74030 (9)	0.40923 (8)	0.0227 (3)
O2	0.2592 (3)	0.47945 (8)	0.42401 (8)	0.0216 (3)
O3	0.2541 (3)	0.89685 (8)	0.27377 (8)	0.0188 (3)
N1	0.4879 (3)	0.61150 (10)	0.41488 (9)	0.0167 (3)
H1	0.572 (4)	0.5837 (12)	0.4647 (8)	0.014 (5)*
N2	0.4166 (3)	0.73931 (10)	0.29812 (9)	0.0151 (3)
C1	0.5563 (4)	0.69986 (12)	0.37641 (11)	0.0169 (4)
C2	0.2987 (4)	0.55921 (12)	0.38339 (11)	0.0174 (4)
C3	0.1581 (4)	0.60349 (12)	0.30160 (11)	0.0160 (4)
C4	0.2187 (4)	0.69150 (12)	0.26177 (11)	0.0156 (4)
C5	−0.0516 (4)	0.54575 (12)	0.26870 (12)	0.0186 (4)
H5A	−0.1999	0.5869	0.2367	0.022*
H5B	−0.1376	0.5044	0.3205	0.022*
C6	0.0717 (4)	0.48772 (14)	0.20714 (13)	0.0276 (5)
H6A	−0.0749	0.4526	0.1881	0.041*
H6B	0.2147	0.4453	0.2389	0.041*
H6C	0.1542	0.5281	0.1550	0.041*
C7	0.0796 (4)	0.74447 (12)	0.17790 (11)	0.0174 (4)
H7A	0.0081	0.8038	0.1887	0.021*
H7B	−0.0822	0.7096	0.1667	0.021*
C8	0.2569 (4)	0.76452 (12)	0.09395 (11)	0.0165 (4)
C9	0.4438 (4)	0.69892 (12)	0.07253 (12)	0.0184 (4)
H9	0.4670	0.6407	0.1124	0.022*
C10	0.5962 (4)	0.71790 (13)	−0.00650 (12)	0.0208 (4)
C11	0.5603 (4)	0.80409 (13)	−0.06396 (12)	0.0217 (4)
H11	0.6650	0.8178	−0.1175	0.026*
C12	0.3753 (4)	0.87043 (13)	−0.04483 (12)	0.0230 (4)
C13	0.2259 (4)	0.84895 (12)	0.03477 (12)	0.0195 (4)
H13	0.0991	0.8936	0.0488	0.023*
C14	0.7919 (4)	0.64610 (15)	−0.03046 (13)	0.0297 (5)
H14A	0.9592	0.6757	−0.0584	0.045*
H14B	0.7005	0.6158	−0.0719	0.045*
H14C	0.8429	0.6003	0.0234	0.045*
C15	0.3370 (5)	0.96336 (14)	−0.10683 (13)	0.0317 (5)
H15A	0.3628	1.0115	−0.0741	0.048*
H15B	0.1497	0.9693	−0.1316	0.048*
H15C	0.4735	0.9697	−0.1551	0.048*
C16	0.4702 (4)	0.83684 (11)	0.25921 (11)	0.0169 (4)
H16A	0.6428	0.8536	0.2849	0.020*
H16B	0.5000	0.8449	0.1945	0.020*
C17	0.2175 (4)	0.90085 (12)	0.36571 (11)	0.0197 (4)
H17A	0.3996	0.9041	0.3934	0.024*
H17B	0.1242	0.8452	0.3989	0.024*
C18	0.0417 (4)	0.98597 (12)	0.36809 (12)	0.0202 (4)
H18A	−0.0194	0.9832	0.4300	0.024*
H18B	−0.1260	0.9863	0.3318	0.024*
C19	0.1936 (4)	1.07554 (12)	0.33360 (13)	0.0230 (4)
H19A	0.3619	1.0752	0.3697	0.028*
H19B	0.2536	1.0787	0.2715	0.028*
C20	0.0166 (4)	1.15986 (12)	0.33684 (12)	0.0192 (4)
C21	−0.1760 (4)	1.19492 (13)	0.27088 (12)	0.0226 (4)
H21	−0.1878	1.1679	0.2210	0.027*
C22	−0.3515 (4)	1.26880 (13)	0.27654 (13)	0.0248 (4)
H22	−0.4838	1.2912	0.2312	0.030*
C23	−0.3344 (4)	1.31006 (13)	0.34816 (13)	0.0240 (4)
H23	−0.4567	1.3598	0.3528	0.029*
C24	−0.1361 (4)	1.27772 (13)	0.41292 (12)	0.0232 (4)
H24	−0.1187	1.3067	0.4612	0.028*
C25	0.0366 (4)	1.20321 (12)	0.40744 (12)	0.0207 (4)
H25	0.1703	1.1814	0.4524	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0282 (7)	0.0184 (7)	0.0228 (7)	−0.0030 (6)	−0.0061 (6)	−0.0063 (5)
O2	0.0311 (7)	0.0122 (6)	0.0209 (6)	−0.0008 (5)	−0.0045 (6)	−0.0022 (5)
O3	0.0256 (7)	0.0144 (6)	0.0171 (6)	0.0028 (5)	0.0006 (5)	−0.0060 (5)
N1	0.0237 (8)	0.0121 (7)	0.0137 (7)	0.0013 (6)	−0.0042 (6)	−0.0020 (6)
N2	0.0192 (7)	0.0118 (7)	0.0145 (7)	−0.0008 (6)	0.0002 (6)	−0.0036 (6)
C1	0.0189 (9)	0.0156 (9)	0.0175 (8)	0.0010 (7)	0.0010 (7)	−0.0067 (7)
C2	0.0201 (9)	0.0144 (8)	0.0190 (9)	0.0007 (7)	0.0032 (7)	−0.0067 (7)
C3	0.0174 (9)	0.0157 (9)	0.0160 (8)	0.0021 (7)	0.0010 (7)	−0.0065 (7)
C4	0.0183 (8)	0.0146 (9)	0.0147 (8)	0.0020 (7)	0.0019 (7)	−0.0057 (7)
C5	0.0208 (9)	0.0144 (9)	0.0205 (9)	−0.0008 (7)	−0.0019 (7)	−0.0039 (7)
C6	0.0350 (11)	0.0242 (10)	0.0277 (10)	−0.0064 (9)	0.0021 (9)	−0.0138 (8)
C7	0.0188 (9)	0.0152 (9)	0.0177 (8)	0.0009 (7)	0.0003 (7)	−0.0031 (7)
C8	0.0196 (9)	0.0159 (9)	0.0150 (8)	−0.0018 (7)	−0.0023 (7)	−0.0053 (7)
C9	0.0216 (9)	0.0168 (9)	0.0175 (8)	0.0004 (7)	−0.0040 (7)	−0.0053 (7)
C10	0.0206 (9)	0.0242 (10)	0.0195 (9)	0.0012 (8)	−0.0029 (7)	−0.0088 (8)
C11	0.0242 (10)	0.0257 (10)	0.0168 (9)	−0.0047 (8)	0.0026 (7)	−0.0076 (8)
C12	0.0336 (11)	0.0190 (9)	0.0170 (9)	−0.0042 (8)	−0.0011 (8)	−0.0047 (7)
C13	0.0263 (10)	0.0155 (9)	0.0177 (8)	0.0017 (7)	−0.0023 (7)	−0.0062 (7)
C14	0.0300 (11)	0.0360 (12)	0.0249 (10)	0.0083 (9)	0.0005 (8)	−0.0117 (9)
C15	0.0512 (14)	0.0206 (10)	0.0223 (10)	−0.0020 (9)	0.0085 (9)	−0.0033 (8)
C16	0.0214 (9)	0.0117 (8)	0.0174 (8)	0.0006 (7)	0.0025 (7)	−0.0032 (7)
C17	0.0275 (10)	0.0169 (9)	0.0162 (8)	−0.0011 (8)	0.0036 (7)	−0.0067 (7)
C18	0.0242 (9)	0.0174 (9)	0.0212 (9)	−0.0025 (7)	0.0046 (7)	−0.0087 (7)
C19	0.0246 (10)	0.0162 (9)	0.0304 (10)	−0.0007 (8)	0.0049 (8)	−0.0097 (8)
C20	0.0205 (9)	0.0143 (9)	0.0237 (9)	−0.0055 (7)	0.0068 (7)	−0.0058 (7)
C21	0.0276 (10)	0.0193 (9)	0.0233 (9)	−0.0048 (8)	0.0020 (8)	−0.0092 (8)
C22	0.0259 (10)	0.0195 (10)	0.0282 (10)	−0.0029 (8)	−0.0055 (8)	−0.0032 (8)
C23	0.0249 (10)	0.0150 (9)	0.0320 (10)	−0.0001 (8)	0.0035 (8)	−0.0055 (8)
C24	0.0303 (10)	0.0195 (9)	0.0219 (9)	−0.0023 (8)	0.0043 (8)	−0.0094 (8)
C25	0.0231 (9)	0.0175 (9)	0.0215 (9)	−0.0027 (7)	0.0002 (7)	−0.0041 (7)

Geometric parameters (Å, º) top

O1—C1	1.222 (2)	C12—C13	1.397 (3)
O2—C2	1.234 (2)	C12—C15	1.506 (3)
O3—C16	1.404 (2)	C13—H13	0.9500
O3—C17	1.444 (2)	C14—H14A	0.9800
N1—C1	1.368 (2)	C14—H14B	0.9800
N1—C2	1.381 (2)	C14—H14C	0.9800
N1—H1	0.885 (9)	C15—H15A	0.9800
N2—C1	1.393 (2)	C15—H15B	0.9800
N2—C4	1.405 (2)	C15—H15C	0.9800
N2—C16	1.475 (2)	C16—H16A	0.9900
C2—C3	1.454 (2)	C16—H16B	0.9900
C3—C4	1.359 (2)	C17—C18	1.514 (2)
C3—C5	1.514 (2)	C17—H17A	0.9900
C4—C7	1.511 (2)	C17—H17B	0.9900
C5—C6	1.529 (3)	C18—C19	1.530 (3)
C5—H5A	0.9900	C18—H18A	0.9900
C5—H5B	0.9900	C18—H18B	0.9900
C6—H6A	0.9800	C19—C20	1.511 (2)
C6—H6B	0.9800	C19—H19A	0.9900
C6—H6C	0.9800	C19—H19B	0.9900
C7—C8	1.523 (2)	C20—C21	1.390 (3)
C7—H7A	0.9900	C20—C25	1.395 (3)
C7—H7B	0.9900	C21—C22	1.389 (3)
C8—C13	1.386 (2)	C21—H21	0.9500
C8—C9	1.404 (2)	C22—C23	1.388 (3)
C9—C10	1.395 (2)	C22—H22	0.9500
C9—H9	0.9500	C23—C24	1.389 (3)
C10—C11	1.397 (3)	C23—H23	0.9500
C10—C14	1.513 (3)	C24—C25	1.388 (3)
C11—C12	1.393 (3)	C24—H24	0.9500
C11—H11	0.9500	C25—H25	0.9500

C16—O3—C17	113.95 (13)	C10—C14—H14A	109.5
C1—N1—C2	126.47 (14)	C10—C14—H14B	109.5
C1—N1—H1	118.3 (13)	H14A—C14—H14B	109.5
C2—N1—H1	115.2 (13)	C10—C14—H14C	109.5
C1—N2—C4	122.09 (14)	H14A—C14—H14C	109.5
C1—N2—C16	116.28 (14)	H14B—C14—H14C	109.5
C4—N2—C16	121.44 (14)	C12—C15—H15A	109.5
O1—C1—N1	121.59 (16)	C12—C15—H15B	109.5
O1—C1—N2	123.13 (16)	H15A—C15—H15B	109.5
N1—C1—N2	115.28 (15)	C12—C15—H15C	109.5
O2—C2—N1	119.97 (15)	H15A—C15—H15C	109.5
O2—C2—C3	123.88 (16)	H15B—C15—H15C	109.5
N1—C2—C3	116.15 (15)	O3—C16—N2	113.40 (14)
C4—C3—C2	119.14 (16)	O3—C16—H16A	108.9
C4—C3—C5	125.36 (15)	N2—C16—H16A	108.9
C2—C3—C5	115.50 (15)	O3—C16—H16B	108.9
C3—C4—N2	120.86 (15)	N2—C16—H16B	108.9
C3—C4—C7	123.32 (16)	H16A—C16—H16B	107.7
N2—C4—C7	115.82 (14)	O3—C17—C18	107.67 (14)
C3—C5—C6	113.79 (15)	O3—C17—H17A	110.2
C3—C5—H5A	108.8	C18—C17—H17A	110.2
C6—C5—H5A	108.8	O3—C17—H17B	110.2
C3—C5—H5B	108.8	C18—C17—H17B	110.2
C6—C5—H5B	108.8	H17A—C17—H17B	108.5
H5A—C5—H5B	107.7	C17—C18—C19	113.32 (15)
C5—C6—H6A	109.5	C17—C18—H18A	108.9
C5—C6—H6B	109.5	C19—C18—H18A	108.9
H6A—C6—H6B	109.5	C17—C18—H18B	108.9
C5—C6—H6C	109.5	C19—C18—H18B	108.9
H6A—C6—H6C	109.5	H18A—C18—H18B	107.7
H6B—C6—H6C	109.5	C20—C19—C18	112.78 (15)
C4—C7—C8	116.78 (14)	C20—C19—H19A	109.0
C4—C7—H7A	108.1	C18—C19—H19A	109.0
C8—C7—H7A	108.1	C20—C19—H19B	109.0
C4—C7—H7B	108.1	C18—C19—H19B	109.0
C8—C7—H7B	108.1	H19A—C19—H19B	107.8
H7A—C7—H7B	107.3	C21—C20—C25	118.12 (17)
C13—C8—C9	118.59 (16)	C21—C20—C19	120.98 (16)
C13—C8—C7	119.19 (16)	C25—C20—C19	120.87 (17)
C9—C8—C7	122.17 (15)	C22—C21—C20	121.14 (17)
C10—C9—C8	120.99 (17)	C22—C21—H21	119.4
C10—C9—H9	119.5	C20—C21—H21	119.4
C8—C9—H9	119.5	C23—C22—C21	120.25 (18)
C11—C10—C9	118.59 (17)	C23—C22—H22	119.9
C11—C10—C14	120.58 (17)	C21—C22—H22	119.9
C9—C10—C14	120.82 (17)	C22—C23—C24	119.15 (17)
C12—C11—C10	121.78 (17)	C22—C23—H23	120.4
C12—C11—H11	119.1	C24—C23—H23	120.4
C10—C11—H11	119.1	C25—C24—C23	120.34 (17)
C11—C12—C13	118.06 (17)	C25—C24—H24	119.8
C11—C12—C15	121.73 (17)	C23—C24—H24	119.8
C13—C12—C15	120.21 (17)	C24—C25—C20	120.95 (17)
C8—C13—C12	121.99 (17)	C24—C25—H25	119.5
C8—C13—H13	119.0	C20—C25—H25	119.5
C12—C13—H13	119.0

C2—N1—C1—O1	−179.48 (16)	C7—C8—C9—C10	177.55 (16)
C2—N1—C1—N2	0.4 (2)	C8—C9—C10—C11	0.4 (3)
C4—N2—C1—O1	−179.83 (16)	C8—C9—C10—C14	−178.39 (17)
C16—N2—C1—O1	−4.8 (2)	C9—C10—C11—C12	−0.8 (3)
C4—N2—C1—N1	0.3 (2)	C14—C10—C11—C12	178.03 (17)
C16—N2—C1—N1	175.32 (14)	C10—C11—C12—C13	0.6 (3)
C1—N1—C2—O2	178.90 (16)	C10—C11—C12—C15	179.97 (19)
C1—N1—C2—C3	−0.5 (3)	C9—C8—C13—C12	−0.3 (3)
O2—C2—C3—C4	−179.46 (17)	C7—C8—C13—C12	−177.79 (16)
N1—C2—C3—C4	−0.1 (2)	C11—C12—C13—C8	−0.1 (3)
O2—C2—C3—C5	1.5 (2)	C15—C12—C13—C8	−179.45 (18)
N1—C2—C3—C5	−179.14 (15)	C17—O3—C16—N2	66.98 (18)
C2—C3—C4—N2	0.7 (2)	C1—N2—C16—O3	−103.56 (17)
C5—C3—C4—N2	179.69 (15)	C4—N2—C16—O3	71.52 (19)
C2—C3—C4—C7	−178.51 (15)	C16—O3—C17—C18	163.75 (14)
C5—C3—C4—C7	0.5 (3)	O3—C17—C18—C19	−70.60 (19)
C1—N2—C4—C3	−0.9 (2)	C17—C18—C19—C20	−179.67 (15)
C16—N2—C4—C3	−175.63 (15)	C18—C19—C20—C21	−81.0 (2)
C1—N2—C4—C7	178.43 (14)	C18—C19—C20—C25	97.2 (2)
C16—N2—C4—C7	3.6 (2)	C25—C20—C21—C22	−2.5 (3)
C4—C3—C5—C6	91.8 (2)	C19—C20—C21—C22	175.80 (17)
C2—C3—C5—C6	−89.18 (19)	C20—C21—C22—C23	1.0 (3)
C3—C4—C7—C8	−110.06 (19)	C21—C22—C23—C24	1.3 (3)
N2—C4—C7—C8	70.7 (2)	C22—C23—C24—C25	−2.0 (3)
C4—C7—C8—C13	−141.21 (17)	C23—C24—C25—C20	0.5 (3)
C4—C7—C8—C9	41.3 (2)	C21—C20—C25—C24	1.7 (3)
C13—C8—C9—C10	0.1 (3)	C19—C20—C25—C24	−176.55 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.89 (1)	1.94 (1)	2.826 (2)	178 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₅H₃₀N₂O₃
M_r	406.51
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	4.8276 (4), 14.9398 (10), 15.4574 (12)
α, β, γ (°)	76.949 (6), 89.296 (6), 88.267 (6)
V (Å³)	1085.53 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.20 × 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	0.980, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	7623, 4974, 3719
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.167, 1.04
No. of reflections	4974
No. of parameters	277
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)	0.39, −0.29

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	0.89 (1)	1.94 (1)	2.826 (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, Oxfordshire, 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 o316

doi:10.1107/S1600536811055723

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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-[(3-phenyl­prop­­oxy)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-[(3-phenylpropoxy)methyl]-1,2,3,4-tetrahydropyrimidine-2,4-dione