Ethyl 6-methyl-3-(2-methyl­prop-1-en­yl)-2-oxo-4-phenyl-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

Wang, X.-C.; Tang, X.-H.; Da, Y.-X.; Zhang, Z.; Quan, Z.-J.

doi:10.1107/S1600536811042243

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2993

doi:10.1107/S1600536811042243

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Ethyl 6-methyl-3-(2-methylprop-1-enyl)-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Xi-Cun Wang,^a ^* Xue-Hong Tang,^a Yu-Xia Da,^a Zhang Zhang ^a and Zheng-Jun Quan ^a

^aGansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: wangxicun@nwnu.edu.cn

(Received 3 October 2011; accepted 13 October 2011; online 22 October 2011)

In the molecule of the title compound, C₁₈H₂₂N₂O₃, the dihydropyrimidinone ring adopts an envelope conformation. The dihedral angle between the phenyl ring and the mean plane through the enamine fragment is 86.04 (7)°. The molecular conformation is stabilized by an intramolecular C—H⋯O hydrogen bond. In the crystal, intermolecular N—H⋯O hydrogen bonds link pairs of molecules into centrosymmetric dimers.

Related literature

For general background to and pharmaceutical applications of pyrimidinones, see: Atwal (1990 ); Matsuda & Hirao (1965 ); Müller et al. (2008 ). For a related structure, see: Fun et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₈H₂₂N₂O₃
M_r = 314.38
Monoclinic, P 2₁ /c
a = 14.114 (4) Å
b = 8.298 (2) Å
c = 14.629 (4) Å
β = 93.959 (2)°
V = 1709.3 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.25 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.979, T_max = 0.982
11929 measured reflections
3180 independent reflections
2474 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.129
S = 0.96
3180 reflections
216 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.42 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
C18—H18⋯O2	0.93	2.58	3.176 (3)	123
N1—H1⋯O1ⁱ	0.85 (2)	2.06 (2)	2.915 (2)	177 (2)
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811042243/rz2648sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811042243/rz2648Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811042243/rz2648Isup3.cml

checkCIF report

Comment top

3,4-Dihydropyrimidinones are compounds that have been drawn widespread attention due to their pharmaceutical applications. A variety of dihydropyrimidinone derivatives have been screened for antihypertension (Atwal, 1990) and antibacterial (Matsuda & Hirao, 1965) activities. At the same time, nitrogen-containing compounds, such as amines, enamines, and imines, are valuable and commercially important bulk chemicals, specialty chemicals, and pharmaceuticals (Müller et al., 2008). As a result, dihydropyrimidin-2-ones-containing enamines can be synthesized by a new approach. As a continuation of our study on series of dihydropyrimidinone derivatives, we report herein the crystal structure of the title compound.

In the title compound (Fig. 1) bond lengths (Allen et al., 1987) and angles are within normal ranges, and are comparable with those observed in a closely related structure (Fun et al., 2009). The six-membered dihydropyrimidinone ring assumes an envelope conformation, with atom C4 displaced by 0.478 (2) Å from the mean plane of the other atoms. The dihedral angles formed by the mean plane through the enamine fragment (N2/C9–C12) and the phenyl ring is 86.04 (7)°. An intramolecular C—H···O hydrogen bond stabilizes the molecular conformation (Table 1). In the crystal, pairs of centrosymmetrically related molecules are linked by N—H···O hydrogen bonds into dimers (Fig. 2) generating rings of R₂²(8) graph-set motif.

Related literature top

For general background to and pharmaceutical applications of pyrimidinones, see: Atwal (1990); Matsuda & Hirao (1965); Müller et al. (2008). For a related structure, see: Fun et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was synthesized by refluxing a mixture of 3,4-dihydropyrimidinone (1.0 mmol), isobutyraldehyde (2.0 mmol), and trimethylsilyl chloride (2.5 mmol) in anhydrous CH₂Cl₂ (10 ml) for 12 h. After completion of the reaction monitored by thin layer chromatography (TLC), the crude product was purified by column chromatography over silica gel with ethyl acetate/petroleum ether (1:1 v/v to afford the pure the title compound as the unique product. Crystals suitable for X-ray diffraction analysis were obtained on slow evaporation of an ethanol solution (yield 75%).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 30% probability level. H atoms are omitted.
	Fig. 2. A view of a centrosymmetric dimeric unit formed via intermolecular hydrogen bonds (dashed lines) in the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Ethyl 6-methyl-3-(2-methylprop-1-enyl)-2-oxo-4-phenyl- 1,2,3,4-tetrahydropyrimidine-5-carboxylate top

Crystal data top

C₁₈H₂₂N₂O₃	F(000) = 672
M_r = 314.38	D_x = 1.222 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4330 reflections
a = 14.114 (4) Å	θ = 2.8–26.4°
b = 8.298 (2) Å	µ = 0.08 mm⁻¹
c = 14.629 (4) Å	T = 296 K
β = 93.959 (2)°	Block, colourless
V = 1709.3 (8) Å³	0.25 × 0.24 × 0.22 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	3180 independent reflections
Radiation source: fine-focus sealed tube	2474 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −16→17
T_min = 0.979, T_max = 0.982	k = −10→8
11929 measured reflections	l = −17→17

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.0463P)² + 1.3266P] where P = (F_o² + 2F_c²)/3
3180 reflections	(Δ/σ)_max = 0.001
216 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₁₈H₂₂N₂O₃	V = 1709.3 (8) Å³
M_r = 314.38	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 14.114 (4) Å	µ = 0.08 mm⁻¹
b = 8.298 (2) Å	T = 296 K
c = 14.629 (4) Å	0.25 × 0.24 × 0.22 mm
β = 93.959 (2)°

Data collection top

Bruker APEXII CCD diffractometer	3180 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	2474 reflections with I > 2σ(I)
T_min = 0.979, T_max = 0.982	R_int = 0.020
11929 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.42 e Å⁻³
3180 reflections	Δρ_min = −0.33 e Å⁻³
216 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
C1	0.72325 (13)	0.1486 (2)	0.41220 (12)	0.0366 (4)
C2	0.77888 (13)	0.0257 (2)	0.44302 (13)	0.0388 (4)
C3	0.92081 (13)	0.1942 (2)	0.44340 (12)	0.0371 (4)
C4	0.76336 (12)	0.3183 (2)	0.41569 (13)	0.0365 (4)
H4	0.7332	0.3778	0.3636	0.044*
C5	0.62397 (14)	0.1386 (3)	0.37604 (14)	0.0437 (5)
C6	0.48677 (19)	−0.0234 (4)	0.3462 (2)	0.0869 (10)
H6A	0.4503	0.0676	0.3662	0.104*
H6B	0.4827	−0.0246	0.2798	0.104*
C7	0.4492 (2)	−0.1689 (5)	0.3797 (2)	0.1148 (14)
H7A	0.4801	−0.2590	0.3534	0.172*
H7B	0.3822	−0.1738	0.3631	0.172*
H7C	0.4598	−0.1723	0.4452	0.172*
C8	0.75390 (16)	−0.1477 (3)	0.45539 (18)	0.0582 (6)
H8A	0.6965	−0.1551	0.4867	0.087*
H8B	0.8045	−0.2006	0.4909	0.087*
H8C	0.7447	−0.1986	0.3965	0.087*
C9	0.91126 (13)	0.4621 (2)	0.38297 (14)	0.0423 (5)
H9	0.9533	0.5070	0.4277	0.051*
C10	0.89706 (15)	0.5394 (3)	0.30492 (15)	0.0497 (5)
C11	0.9448 (2)	0.7003 (3)	0.2919 (2)	0.0760 (8)
H11A	0.9780	0.7327	0.3485	0.114*
H11B	0.8977	0.7796	0.2738	0.114*
H11C	0.9891	0.6907	0.2453	0.114*
C12	0.8374 (2)	0.4801 (4)	0.22492 (17)	0.0868 (9)
H12A	0.8216	0.3690	0.2342	0.130*
H12B	0.8717	0.4900	0.1707	0.130*
H12C	0.7802	0.5427	0.2179	0.130*
C13	0.73992 (13)	0.4064 (2)	0.50270 (14)	0.0406 (5)
C14	0.79880 (18)	0.4024 (3)	0.58146 (16)	0.0579 (6)
H14	0.8564	0.3481	0.5816	0.070*
C15	0.7738 (2)	0.4779 (3)	0.66064 (19)	0.0778 (8)
H15	0.8146	0.4739	0.7133	0.093*
C16	0.6894 (2)	0.5584 (3)	0.6617 (2)	0.0795 (9)
H16	0.6726	0.6086	0.7150	0.095*
C17	0.6301 (2)	0.5647 (3)	0.5843 (2)	0.0730 (8)
H17	0.5726	0.6193	0.5849	0.088*
C18	0.65490 (15)	0.4902 (3)	0.50460 (18)	0.0551 (6)
H18	0.6143	0.4964	0.4519	0.066*
N1	0.87357 (11)	0.0582 (2)	0.46786 (12)	0.0415 (4)
N2	0.86624 (10)	0.31325 (18)	0.40381 (11)	0.0374 (4)
O1	1.00791 (9)	0.20302 (17)	0.45540 (10)	0.0488 (4)
O2	0.57967 (10)	0.2533 (2)	0.34516 (12)	0.0628 (5)
O3	0.58555 (10)	−0.0075 (2)	0.38094 (12)	0.0618 (5)
H1	0.9093 (16)	−0.018 (3)	0.4888 (15)	0.052 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0337 (10)	0.0370 (10)	0.0396 (10)	−0.0014 (8)	0.0047 (8)	0.0009 (8)
C2	0.0366 (10)	0.0362 (10)	0.0439 (10)	−0.0029 (8)	0.0062 (8)	0.0002 (8)
C3	0.0342 (10)	0.0368 (10)	0.0408 (10)	0.0020 (8)	0.0050 (8)	0.0024 (8)
C4	0.0295 (9)	0.0357 (10)	0.0444 (10)	0.0011 (8)	0.0028 (7)	0.0067 (8)
C5	0.0379 (11)	0.0466 (12)	0.0467 (11)	−0.0047 (9)	0.0040 (8)	−0.0024 (9)
C6	0.0550 (16)	0.082 (2)	0.120 (2)	−0.0265 (15)	−0.0249 (16)	0.0113 (18)
C7	0.086 (2)	0.162 (4)	0.094 (2)	−0.071 (2)	−0.0088 (18)	0.022 (2)
C8	0.0497 (13)	0.0388 (12)	0.0861 (17)	−0.0040 (10)	0.0037 (12)	0.0065 (11)
C9	0.0349 (10)	0.0401 (11)	0.0520 (12)	−0.0039 (8)	0.0029 (8)	0.0080 (9)
C10	0.0520 (12)	0.0454 (12)	0.0524 (12)	0.0005 (10)	0.0096 (10)	0.0089 (10)
C11	0.0805 (18)	0.0615 (16)	0.0869 (19)	−0.0118 (14)	0.0118 (15)	0.0278 (14)
C12	0.125 (3)	0.087 (2)	0.0479 (14)	−0.0181 (19)	0.0008 (15)	0.0073 (14)
C13	0.0396 (10)	0.0284 (10)	0.0548 (12)	−0.0030 (8)	0.0101 (9)	0.0036 (8)
C14	0.0628 (14)	0.0543 (14)	0.0564 (13)	0.0086 (12)	0.0015 (11)	−0.0065 (11)
C15	0.106 (2)	0.0690 (18)	0.0584 (15)	0.0009 (17)	0.0081 (15)	−0.0119 (13)
C16	0.106 (2)	0.0566 (17)	0.081 (2)	−0.0116 (16)	0.0432 (18)	−0.0182 (14)
C17	0.0653 (16)	0.0461 (14)	0.112 (2)	0.0006 (12)	0.0415 (16)	−0.0130 (15)
C18	0.0432 (12)	0.0420 (12)	0.0813 (16)	0.0004 (10)	0.0141 (11)	−0.0041 (11)
N1	0.0340 (9)	0.0335 (9)	0.0569 (10)	0.0033 (7)	0.0017 (7)	0.0096 (8)
N2	0.0305 (8)	0.0344 (9)	0.0476 (9)	0.0014 (7)	0.0051 (6)	0.0078 (7)
O1	0.0296 (7)	0.0477 (9)	0.0691 (9)	0.0014 (6)	0.0025 (6)	0.0112 (7)
O2	0.0429 (8)	0.0586 (10)	0.0841 (11)	0.0027 (8)	−0.0149 (8)	0.0068 (9)
O3	0.0425 (8)	0.0567 (10)	0.0846 (12)	−0.0162 (7)	−0.0085 (8)	0.0058 (8)

Geometric parameters (Å, º) top

C1—C2	1.346 (3)	C9—C10	1.313 (3)
C1—C5	1.465 (3)	C9—N2	1.432 (2)
C1—C4	1.517 (3)	C9—H9	0.9300
C2—N1	1.387 (2)	C10—C12	1.478 (3)
C2—C8	1.495 (3)	C10—C11	1.514 (3)
C3—O1	1.232 (2)	C11—H11A	0.9600
C3—N2	1.357 (2)	C11—H11B	0.9600
C3—N1	1.371 (2)	C11—H11C	0.9600
C4—N2	1.475 (2)	C12—H12A	0.9600
C4—C13	1.524 (3)	C12—H12B	0.9600
C4—H4	0.9800	C12—H12C	0.9600
C5—O2	1.209 (2)	C13—C14	1.374 (3)
C5—O3	1.332 (3)	C13—C18	1.389 (3)
C6—C7	1.419 (4)	C14—C15	1.384 (3)
C6—O3	1.457 (3)	C14—H14	0.9300
C6—H6A	0.9700	C15—C16	1.366 (4)
C6—H6B	0.9700	C15—H15	0.9300
C7—H7A	0.9600	C16—C17	1.362 (4)
C7—H7B	0.9600	C16—H16	0.9300
C7—H7C	0.9600	C17—C18	1.386 (4)
C8—H8A	0.9600	C17—H17	0.9300
C8—H8B	0.9600	C18—H18	0.9300
C8—H8C	0.9600	N1—H1	0.85 (2)

C2—C1—C5	126.84 (18)	C9—C10—C11	119.8 (2)
C2—C1—C4	118.95 (16)	C12—C10—C11	115.4 (2)
C5—C1—C4	114.19 (16)	C10—C11—H11A	109.5
C1—C2—N1	118.06 (17)	C10—C11—H11B	109.5
C1—C2—C8	129.24 (18)	H11A—C11—H11B	109.5
N1—C2—C8	112.70 (17)	C10—C11—H11C	109.5
O1—C3—N2	123.30 (17)	H11A—C11—H11C	109.5
O1—C3—N1	120.66 (17)	H11B—C11—H11C	109.5
N2—C3—N1	116.02 (16)	C10—C12—H12A	109.5
N2—C4—C1	109.75 (15)	C10—C12—H12B	109.5
N2—C4—C13	112.60 (15)	H12A—C12—H12B	109.5
C1—C4—C13	111.80 (15)	C10—C12—H12C	109.5
N2—C4—H4	107.5	H12A—C12—H12C	109.5
C1—C4—H4	107.5	H12B—C12—H12C	109.5
C13—C4—H4	107.5	C14—C13—C18	118.0 (2)
O2—C5—O3	122.32 (18)	C14—C13—C4	122.37 (18)
O2—C5—C1	123.19 (19)	C18—C13—C4	119.65 (19)
O3—C5—C1	114.49 (18)	C13—C14—C15	121.1 (2)
C7—C6—O3	109.2 (3)	C13—C14—H14	119.4
C7—C6—H6A	109.8	C15—C14—H14	119.4
O3—C6—H6A	109.8	C16—C15—C14	120.2 (3)
C7—C6—H6B	109.8	C16—C15—H15	119.9
O3—C6—H6B	109.8	C14—C15—H15	119.9
H6A—C6—H6B	108.3	C17—C16—C15	119.7 (3)
C6—C7—H7A	109.5	C17—C16—H16	120.1
C6—C7—H7B	109.5	C15—C16—H16	120.1
H7A—C7—H7B	109.5	C16—C17—C18	120.4 (3)
C6—C7—H7C	109.5	C16—C17—H17	119.8
H7A—C7—H7C	109.5	C18—C17—H17	119.8
H7B—C7—H7C	109.5	C17—C18—C13	120.6 (2)
C2—C8—H8A	109.5	C17—C18—H18	119.7
C2—C8—H8B	109.5	C13—C18—H18	119.7
H8A—C8—H8B	109.5	C3—N1—C2	124.64 (17)
C2—C8—H8C	109.5	C3—N1—H1	114.6 (15)
H8A—C8—H8C	109.5	C2—N1—H1	119.2 (15)
H8B—C8—H8C	109.5	C3—N2—C9	118.14 (15)
C10—C9—N2	124.28 (19)	C3—N2—C4	120.31 (15)
C10—C9—H9	117.9	C9—N2—C4	117.11 (15)
N2—C9—H9	117.9	C5—O3—C6	116.56 (19)
C9—C10—C12	124.8 (2)

C5—C1—C2—N1	174.98 (18)	C15—C16—C17—C18	−0.1 (4)
C4—C1—C2—N1	−6.5 (3)	C16—C17—C18—C13	0.8 (4)
C5—C1—C2—C8	−5.1 (4)	C14—C13—C18—C17	−1.1 (3)
C4—C1—C2—C8	173.4 (2)	C4—C13—C18—C17	176.9 (2)
C2—C1—C4—N2	31.5 (2)	O1—C3—N1—C2	−168.31 (18)
C5—C1—C4—N2	−149.80 (16)	N2—C3—N1—C2	10.0 (3)
C2—C1—C4—C13	−94.2 (2)	C1—C2—N1—C3	−16.6 (3)
C5—C1—C4—C13	84.5 (2)	C8—C2—N1—C3	163.42 (19)
C2—C1—C5—O2	−176.1 (2)	O1—C3—N2—C9	−6.1 (3)
C4—C1—C5—O2	5.3 (3)	N1—C3—N2—C9	175.65 (16)
C2—C1—C5—O3	4.7 (3)	O1—C3—N2—C4	−161.77 (18)
C4—C1—C5—O3	−173.87 (17)	N1—C3—N2—C4	20.0 (3)
N2—C9—C10—C12	−4.0 (4)	C10—C9—N2—C3	134.3 (2)
N2—C9—C10—C11	177.0 (2)	C10—C9—N2—C4	−69.3 (3)
N2—C4—C13—C14	−33.4 (3)	C1—C4—N2—C3	−38.9 (2)
C1—C4—C13—C14	90.7 (2)	C13—C4—N2—C3	86.3 (2)
N2—C4—C13—C18	148.68 (18)	C1—C4—N2—C9	165.15 (16)
C1—C4—C13—C18	−87.2 (2)	C13—C4—N2—C9	−69.6 (2)
C18—C13—C14—C15	0.7 (3)	O2—C5—O3—C6	0.5 (3)
C4—C13—C14—C15	−177.2 (2)	C1—C5—O3—C6	179.7 (2)
C13—C14—C15—C16	0.0 (4)	C7—C6—O3—C5	−163.3 (3)
C14—C15—C16—C17	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2	0.93	2.58	3.176 (3)	123
N1—H1···O1ⁱ	0.85 (2)	2.06 (2)	2.915 (2)	177 (2)

Symmetry code: (i) −x+2, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₂O₃
M_r	314.38
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	14.114 (4), 8.298 (2), 14.629 (4)
β (°)	93.959 (2)
V (Å³)	1709.3 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.24 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2008)
T_min, T_max	0.979, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	11929, 3180, 2474
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.129, 0.96
No. of reflections	3180
No. of parameters	216
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.33

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2	0.93	2.58	3.176 (3)	122.6
N1—H1···O1ⁱ	0.85 (2)	2.06 (2)	2.915 (2)	177 (2)

Symmetry code: (i) −x+2, −y, −z+1.

Acknowledgements

We are thankful for financial support from the National Nature Science Foundation of China (Nos. 20902073 and 21062017), the Natural Science Foundation of Gansu Province (No. 096RJZA116), and the Scientific and Technological Innovation Engineering Program of Northwest Normal University (nwnu-kjcxgc-03–64, nwnu-lkqn-10–15).

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. CrossRef Web of Science Google Scholar
Atwal, K. S. (1990). J. Med. Chem. 33, 1510–1515. CSD CrossRef CAS PubMed Web of Science Google Scholar
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fun, H.-K., Yeap, C. S., Babu, M. & Kalluraya, B. (2009). Acta Cryst. E65, o1188–o1189. Web of Science CSD CrossRef IUCr Journals Google Scholar
Matsuda, T. & Hirao, I. (1965). Nippon Kagaku Zasshi, 86, 1195–1197. CAS Google Scholar
Müller, T. E., Hultzsch, K. C., Yus, M., Foubelo, F. & Tada, M. (2008). Chem. Rev. 108, 3795–3892. PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 11| November 2011| Page o2993

doi:10.1107/S1600536811042243

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

Ethyl 6-methyl-3-(2-methyl­prop-1-en­yl)-2-oxo-4-phenyl-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Ethyl 6-methyl-3-(2-methylprop-1-enyl)-2-oxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxylate