Ethyl 6-methyl-2-oxo-4-phenyl-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

The title compound, C(14)H(16)N(2)O(3), belongs to a group of esters of 2-oxo- and 1,2,3,4-tetra-hydro-pyrimidine-5-carboxylic acids, which exhibit a wide spectrum of biological activities. The dihydro-pyrimidine ring adopts a screw-boat conformation. The crystal packing is stabilized by strong N-H⋯O and weak C-H⋯O inter-molecular hydrogen bonds. An intra-molecular C-H⋯O hydrogen bond is also present.

Related literature

For related literature, see: Atwal et al. (1991 ▶); Broughton et al. (1975 ▶); Cremer & Pople (1975 ▶); Kappe et al. (1997 ▶); Li et al. (2005 ▶); Nardelli (1983 ▶); Overman et al. (1995 ▶).

Experimental

Crystal data

C14H16N2O3

M = 260.29

Triclinic,

a = 7.5495 (2) Å

b = 8.9797 (3) Å

c = 11.0812 (3) Å

α = 107.843 (2)°

β = 108.603 (1)°

γ = 98.244 (2)°

V = 653.07 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 (2) K

0.3 × 0.2 × 0.2 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: none

16135 measured reflections

3710 independent reflections

2972 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.159

S = 1.00

3710 reflections

174 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808025610/bt2758sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808025610/bt2758Isup2.hkl

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

C14H16N2O3	Z = 2
Mr = 260.29	F000 = 276
Triclinic, P1	Dx = 1.324 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 7.5495 (2) Å	Cell parameters from 5321 reflections
b = 8.9797 (3) Å	θ = 2.5–24.1º
c = 11.0812 (3) Å	µ = 0.09 mm−1
α = 107.843 (2)º	T = 293 (2) K
β = 108.603 (1)º	Needle, colourless
γ = 98.244 (2)º	0.3 × 0.2 × 0.2 mm
V = 653.07 (4) Å3

Bruker APEXII CCD area-detector diffractometer	2972 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
Monochromator: graphite	θmax = 29.7º
T = 293(2) K	θmin = 2.5º
ω and φ scans	h = −9→10
Absorption correction: None	k = −12→12
16135 measured reflections	l = −15→15
3710 independent reflections

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)] = 0.047	H-atom parameters constrained
wR(F2) = 0.159	w = 1/[σ2(Fo2) + (0.0959P)2 + 0.106P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
3710 reflections	Δρmax = 0.34 e Å−3
174 parameters	Δρmin = −0.33 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
O1	−0.18468 (12)	0.90274 (12)	0.54481 (10)	0.0472 (2)
O2	0.51966 (14)	0.59340 (12)	0.67258 (11)	0.0546 (3)
O3	0.30937 (13)	0.47104 (11)	0.73822 (10)	0.0473 (2)
N1	−0.09885 (13)	0.70875 (12)	0.62494 (10)	0.0389 (2)
H1	−0.2165	0.6651	0.6107	0.047*
N2	0.10294 (14)	0.85056 (13)	0.55737 (11)	0.0413 (2)
H2	0.1288	0.9264	0.5285	0.050*
C1	0.2277 (2)	0.89996 (17)	0.91862 (15)	0.0542 (3)
H1A	0.2782	0.9495	0.8699	0.065*
C2	0.2660 (3)	0.9866 (2)	1.05616 (17)	0.0711 (5)
H2A	0.3398	1.0942	1.0982	0.085*
C3	0.1961 (3)	0.9148 (3)	1.12917 (17)	0.0757 (5)
H3	0.2226	0.9726	1.2212	0.091*
C4	0.0872 (4)	0.7575 (3)	1.0669 (2)	0.0860 (6)
H4	0.0400	0.7079	1.1170	0.103*
C5	0.0461 (3)	0.6709 (2)	0.93002 (18)	0.0663 (4)
H5	−0.0292	0.5638	0.8885	0.080*
C6	0.11595 (16)	0.74226 (14)	0.85451 (12)	0.0380 (2)
C7	0.05617 (15)	0.65119 (13)	0.70151 (12)	0.0351 (2)
H7	0.0032	0.5360	0.6808	0.042*
C8	−0.06779 (16)	0.82505 (14)	0.57613 (12)	0.0363 (2)
C9	0.23610 (16)	0.76219 (13)	0.58195 (12)	0.0371 (2)
C10	0.22084 (15)	0.66550 (13)	0.65175 (11)	0.0353 (2)
C11	0.3835 (2)	0.7861 (2)	0.52121 (17)	0.0556 (4)
H11A	0.5017	0.8612	0.5918	0.083*
H11B	0.3354	0.8286	0.4511	0.083*
H11C	0.4080	0.6839	0.4817	0.083*
C12	0.36538 (16)	0.57600 (13)	0.68571 (12)	0.0387 (2)
C13	0.4443 (2)	0.37945 (18)	0.77957 (16)	0.0533 (3)
H13A	0.5686	0.4526	0.8461	0.064*
H13B	0.4638	0.3116	0.7006	0.064*
C14	0.3605 (3)	0.2774 (2)	0.8412 (2)	0.0736 (5)
H14A	0.3373	0.3455	0.9171	0.110*
H14B	0.4495	0.2185	0.8729	0.110*
H14C	0.2403	0.2023	0.7733	0.110*

	U11	U22	U33	U12	U13	U23
O1	0.0364 (4)	0.0620 (5)	0.0619 (5)	0.0227 (4)	0.0271 (4)	0.0348 (5)
O2	0.0412 (5)	0.0638 (6)	0.0791 (7)	0.0260 (4)	0.0348 (5)	0.0359 (5)
O3	0.0454 (5)	0.0496 (5)	0.0621 (6)	0.0229 (4)	0.0290 (4)	0.0276 (4)
N1	0.0265 (4)	0.0462 (5)	0.0487 (5)	0.0090 (4)	0.0175 (4)	0.0211 (4)
N2	0.0337 (5)	0.0488 (5)	0.0569 (6)	0.0163 (4)	0.0268 (4)	0.0281 (5)
C1	0.0591 (8)	0.0482 (7)	0.0481 (7)	0.0069 (6)	0.0199 (6)	0.0127 (6)
C2	0.0693 (11)	0.0669 (9)	0.0531 (8)	0.0156 (8)	0.0146 (7)	0.0016 (7)
C3	0.0706 (11)	0.1122 (15)	0.0470 (8)	0.0445 (11)	0.0283 (8)	0.0187 (9)
C4	0.1003 (15)	0.1211 (18)	0.0684 (11)	0.0388 (14)	0.0585 (11)	0.0462 (12)
C5	0.0736 (10)	0.0732 (10)	0.0667 (9)	0.0123 (8)	0.0443 (8)	0.0307 (8)
C6	0.0327 (5)	0.0453 (6)	0.0446 (6)	0.0160 (4)	0.0208 (4)	0.0195 (5)
C7	0.0300 (5)	0.0336 (5)	0.0453 (6)	0.0088 (4)	0.0185 (4)	0.0152 (4)
C8	0.0290 (5)	0.0425 (5)	0.0397 (5)	0.0100 (4)	0.0162 (4)	0.0150 (4)
C9	0.0304 (5)	0.0407 (5)	0.0434 (6)	0.0112 (4)	0.0194 (4)	0.0138 (4)
C10	0.0306 (5)	0.0357 (5)	0.0410 (5)	0.0109 (4)	0.0182 (4)	0.0109 (4)
C11	0.0466 (7)	0.0753 (9)	0.0742 (9)	0.0281 (7)	0.0421 (7)	0.0416 (8)
C12	0.0353 (5)	0.0382 (5)	0.0436 (6)	0.0133 (4)	0.0184 (4)	0.0116 (4)
C13	0.0531 (8)	0.0576 (7)	0.0645 (8)	0.0292 (6)	0.0289 (7)	0.0302 (7)
C14	0.0817 (12)	0.0773 (11)	0.0928 (13)	0.0373 (9)	0.0446 (10)	0.0539 (10)

O1—C8	1.2310 (14)	C5—C6	1.3793 (18)
O2—C12	1.2133 (14)	C5—H5	0.9300
O3—C12	1.3359 (15)	C6—C7	1.5176 (16)
O3—C13	1.4481 (15)	C7—C10	1.5168 (14)
N1—C8	1.3398 (15)	C7—H7	0.9800
N1—C7	1.4716 (15)	C9—C10	1.3436 (16)
N1—H1	0.8600	C9—C11	1.4950 (15)
N2—C8	1.3684 (14)	C10—C12	1.4673 (15)
N2—C9	1.3788 (14)	C11—H11A	0.9600
N2—H2	0.8600	C11—H11B	0.9600
C1—C6	1.3712 (18)	C11—H11C	0.9600
C1—C2	1.393 (2)	C12—O2	1.2133 (14)
C1—H1A	0.9300	C13—C14	1.483 (2)
C2—C3	1.357 (3)	C13—H13A	0.9700
C2—H2A	0.9300	C13—H13B	0.9700
C3—C4	1.362 (3)	C14—H14A	0.9600
C3—H3	0.9300	C14—H14B	0.9600
C4—C5	1.382 (3)	C14—H14C	0.9600
C4—H4	0.9300
C12—O3—C13	116.09 (10)	O1—C8—N2	120.40 (10)
C8—N1—C7	123.94 (9)	N1—C8—N2	115.72 (10)
C8—N1—H1	118.0	C10—C9—N2	119.72 (10)
C7—N1—H1	118.0	C10—C9—C11	127.49 (11)
C8—N2—C9	124.03 (10)	N2—C9—C11	112.77 (10)
C8—N2—H2	118.0	C9—C10—C12	121.18 (10)
C9—N2—H2	118.0	C9—C10—C7	120.31 (10)
C6—C1—C2	120.50 (14)	C12—C10—C7	118.47 (10)
C6—C1—H1A	119.8	C9—C11—H11A	109.5
C2—C1—H1A	119.8	C9—C11—H11B	109.5
C3—C2—C1	120.33 (17)	H11A—C11—H11B	109.5
C3—C2—H2A	119.8	C9—C11—H11C	109.5
C1—C2—H2A	119.8	H11A—C11—H11C	109.5
C2—C3—C4	119.62 (15)	H11B—C11—H11C	109.5
C2—C3—H3	120.2	O2—C12—O3	122.18 (11)
C4—C3—H3	120.2	O2—C12—O3	122.18 (11)
C3—C4—C5	120.60 (17)	O2—C12—C10	126.44 (11)
C3—C4—H4	119.7	O2—C12—C10	126.44 (11)
C5—C4—H4	119.7	O3—C12—C10	111.36 (9)
C6—C5—C4	120.44 (17)	O3—C13—C14	107.69 (12)
C6—C5—H5	119.8	O3—C13—H13A	110.2
C4—C5—H5	119.8	C14—C13—H13A	110.2
C1—C6—C5	118.50 (13)	O3—C13—H13B	110.2
C1—C6—C7	121.28 (11)	C14—C13—H13B	110.2
C5—C6—C7	120.04 (12)	H13A—C13—H13B	108.5
N1—C7—C10	109.36 (9)	C13—C14—H14A	109.5
N1—C7—C6	109.37 (9)	C13—C14—H14B	109.5
C10—C7—C6	114.22 (9)	H14A—C14—H14B	109.5
N1—C7—H7	107.9	C13—C14—H14C	109.5
C10—C7—H7	107.9	H14A—C14—H14C	109.5
C6—C7—H7	107.9	H14B—C14—H14C	109.5
O1—C8—N1	123.84 (10)
C6—C1—C2—C3	1.3 (3)	C8—N2—C9—C11	165.78 (12)
C1—C2—C3—C4	−0.4 (3)	N2—C9—C10—C12	−176.93 (10)
C2—C3—C4—C5	−0.4 (3)	C11—C9—C10—C12	4.52 (19)
C3—C4—C5—C6	0.4 (3)	N2—C9—C10—C7	0.98 (17)
C2—C1—C6—C5	−1.3 (2)	C11—C9—C10—C7	−177.57 (12)
C2—C1—C6—C7	173.94 (13)	N1—C7—C10—C9	18.31 (14)
C4—C5—C6—C1	0.4 (3)	C6—C7—C10—C9	−104.61 (12)
C4—C5—C6—C7	−174.83 (16)	N1—C7—C10—C12	−163.72 (9)
C8—N1—C7—C10	−31.02 (15)	C6—C7—C10—C12	73.35 (12)
C8—N1—C7—C6	94.75 (12)	C13—O3—C12—O2	0.36 (18)
C1—C6—C7—N1	−75.26 (14)	C13—O3—C12—O2	0.36 (18)
C5—C6—C7—N1	99.89 (14)	C13—O3—C12—C10	−178.13 (10)
C1—C6—C7—C10	47.66 (15)	C9—C10—C12—O2	10.07 (19)
C5—C6—C7—C10	−137.19 (13)	C7—C10—C12—O2	−167.88 (12)
C7—N1—C8—O1	−160.27 (11)	C9—C10—C12—O2	10.07 (19)
C7—N1—C8—N2	22.03 (16)	C7—C10—C12—O2	−167.88 (12)
C9—N2—C8—O1	−175.96 (11)	C9—C10—C12—O3	−171.52 (10)
C9—N2—C8—N1	1.82 (17)	C7—C10—C12—O3	10.53 (14)
C8—N2—C9—C10	−12.97 (18)	C12—O3—C13—C14	177.11 (13)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	2.37	3.1773 (13)	156
N2—H2···O1ii	0.86	2.00	2.8568 (13)	178
C11—H11A···O1iii	0.96	2.58	3.1785 (16)	121
C11—H11C···O2	0.96	2.44	2.8379 (17)	105

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	2.37	3.1773 (13)	156
N2—H2⋯O1ii	0.86	2.00	2.8568 (13)	178
C11—H11A⋯O1iii	0.96	2.58	3.1785 (16)	121
C11—H11C⋯O2	0.96	2.44	2.8379 (17)	105

Symmetry codes: (i) ; (ii) ; (iii) .