Ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

The asymmetric unit of the title compound, C(12)H(14)N(2)O(4), contains two independent mol-ecules. In one independent mol-ecule, the furanyl fragment is rotationally disordered between two orientations in a 0.625 (6):0.375 (6) ratio. In the crystal, inter-molecular pyrimidine-pyrimidinone N-H⋯O hydrogen bonds link the mol-ecules into centrosymmetric tetra-mers, which are further associated into ribbons extending in [010] via weak inter-molecular pyrimidine-carboxyl N-H⋯O hydrogen bonds.

Related literature

The Biginelli reaction is the most important procedure in the synthesis of 3,4-dihydro­pyrimidin-2-(1H)-ones, see: Biginelli (1893 ▶). For related structures, see: Nizam Mohideen et al. (2008 ▶); Qing-Fang et al. (2007 ▶).

Experimental

Crystal data

C12H14N2O4

M = 250.25

Monoclinic,

a = 12.1720 (14) Å

b = 13.3180 (15) Å

c = 17.116 (2) Å

α = 90°

β = 118.300 (2)°

γ = 90°

V = 2443.0 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.48 × 0.45 × 0.17 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.983

11604 measured reflections

4298 independent reflections

1943 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.237

S = 0.94

4298 reflections

338 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040456/cv2771sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040456/cv2771Isup2.hkl

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

C12H14N2O4	F(000) = 1056
Mr = 250.25	Dx = 1.361 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1720 (14) Å	Cell parameters from 1664 reflections
b = 13.3180 (15) Å	θ = 2.3–22.3°
c = 17.116 (2) Å	µ = 0.10 mm−1
β = 118.300 (2)°	T = 298 K
V = 2443.0 (5) Å3	Block, yellow
Z = 8	0.48 × 0.45 × 0.17 mm

Bruker SMART APEX CCD area-detector diffractometer	4298 independent reflections
Radiation source: fine-focus sealed tube	1943 reflections with I > 2σ(I)
graphite	Rint = 0.069
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.952, Tmax = 0.983	k = −14→15
11604 measured reflections	l = −20→19

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)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.237	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.1244P)2] where P = (Fo2 + 2Fc2)/3
4298 reflections	(Δ/σ)max = 0.001
338 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	Occ. (<1)
N1	0.0677 (3)	0.8975 (2)	0.4632 (2)	0.0478 (9)
H1	0.0351	0.9555	0.4437	0.057*
N2	0.0574 (3)	0.7467 (2)	0.5219 (2)	0.0479 (8)
H2	0.0468	0.7135	0.5609	0.057*
N3	0.8736 (3)	0.6124 (2)	0.7072 (2)	0.0499 (9)
H3	0.8988	0.5511	0.7182	0.060*
N4	0.8981 (3)	0.7698 (2)	0.6635 (2)	0.0497 (8)
H4	0.9196	0.8075	0.6321	0.060*
O1	−0.0199 (2)	0.88634 (18)	0.55364 (19)	0.0574 (8)
O2	0.3239 (6)	0.8613 (5)	0.5879 (5)	0.086 (2)	0.625 (6)
C4'	0.3192 (18)	0.9228 (13)	0.5941 (13)	0.086 (2)	0.375 (6)
H4'	0.2672	0.9425	0.6173	0.103*	0.375 (6)
O3	0.2203 (2)	0.7669 (2)	0.32562 (17)	0.0565 (8)
O4	0.1728 (3)	0.6108 (2)	0.3447 (2)	0.0686 (9)
O5	0.9657 (3)	0.63333 (18)	0.6200 (2)	0.0600 (8)
O6	0.6054 (4)	0.6411 (3)	0.5976 (3)	0.1107 (13)
O7	0.7327 (3)	0.7358 (2)	0.85737 (19)	0.0690 (9)
O8	0.7471 (3)	0.8936 (2)	0.8223 (2)	0.0780 (10)
C1	0.0329 (3)	0.8474 (3)	0.5145 (3)	0.0456 (10)
C2	0.1585 (3)	0.8589 (3)	0.4384 (3)	0.0429 (10)
H2A	0.1438	0.8907	0.3826	0.052*
C3	0.2873 (4)	0.8830 (3)	0.5074 (3)	0.0559 (11)
C4	0.3859 (8)	0.9166 (7)	0.4951 (7)	0.079 (2)	0.625 (6)
H4A	0.3852	0.9349	0.4424	0.094*	0.625 (6)
C5	0.4870 (15)	0.9164 (9)	0.5815 (12)	0.086 (4)	0.625 (6)
H5	0.5680	0.9359	0.5966	0.103*	0.625 (6)
C6	0.448 (2)	0.8828 (11)	0.6403 (17)	0.091 (4)	0.625 (6)
H6	0.4943	0.8764	0.7016	0.109*	0.625 (6)
O2'	0.3875 (9)	0.8450 (8)	0.5162 (7)	0.079 (2)	0.375 (6)
C5'	0.459 (4)	0.924 (2)	0.636 (3)	0.091 (4)	0.375 (6)
H5'	0.5116	0.9619	0.6855	0.109*	0.375 (6)
C6'	0.492 (3)	0.8685 (16)	0.598 (2)	0.086 (4)	0.375 (6)
H6'	0.5725	0.8445	0.6184	0.103*	0.375 (6)
C7	0.1783 (3)	0.6992 (3)	0.3629 (2)	0.0461 (9)
C8	0.1410 (3)	0.7470 (2)	0.4236 (2)	0.0408 (9)
C9	0.0980 (3)	0.6952 (3)	0.4705 (2)	0.0425 (9)
C10	0.0877 (4)	0.5845 (3)	0.4755 (3)	0.0621 (12)
H10A	0.0024	0.5646	0.4395	0.093*
H10B	0.1149	0.5652	0.5359	0.093*
H10C	0.1390	0.5523	0.4542	0.093*
C11	0.2614 (4)	0.7310 (3)	0.2650 (3)	0.0666 (12)
H11A	0.1938	0.6969	0.2155	0.080*
H11B	0.3299	0.6842	0.2946	0.080*
C12	0.3030 (4)	0.8203 (4)	0.2328 (3)	0.0828 (15)
H12A	0.2344	0.8660	0.2037	0.124*
H12B	0.3312	0.7988	0.1918	0.124*
H12C	0.3700	0.8533	0.2823	0.124*
C13	0.9139 (3)	0.6678 (3)	0.6603 (3)	0.0473 (10)
C14	0.7910 (3)	0.6476 (3)	0.7409 (3)	0.0477 (10)
H14	0.8183	0.6161	0.7989	0.057*
C15	0.6605 (4)	0.6159 (3)	0.6829 (3)	0.0588 (12)
C16	0.5810 (5)	0.5651 (4)	0.7005 (4)	0.0925 (17)
H16	0.5969	0.5387	0.7552	0.111*
C17	0.4691 (6)	0.5587 (5)	0.6215 (6)	0.113 (2)
H17	0.3961	0.5281	0.6141	0.136*
C18	0.4851 (6)	0.6031 (6)	0.5604 (6)	0.126 (3)
H18	0.4254	0.6087	0.5011	0.151*
C19	0.7596 (4)	0.8057 (3)	0.8129 (3)	0.0563 (11)
C20	0.8035 (3)	0.7603 (3)	0.7555 (2)	0.0452 (9)
C21	0.8509 (3)	0.8162 (3)	0.7128 (2)	0.0444 (9)
C22	0.8605 (4)	0.9280 (3)	0.7135 (3)	0.0591 (12)
H22A	0.7799	0.9562	0.6756	0.089*
H22B	0.9178	0.9474	0.6924	0.089*
H22C	0.8901	0.9524	0.7729	0.089*
C23	0.6852 (5)	0.7708 (4)	0.9158 (3)	0.0831 (15)
H23A	0.6148	0.8154	0.8839	0.100*
H23B	0.7496	0.8074	0.9654	0.100*
C24	0.6464 (5)	0.6833 (5)	0.9477 (4)	0.110 (2)
H24A	0.5780	0.6508	0.8987	0.165*
H24B	0.6206	0.7041	0.9903	0.165*
H24C	0.7150	0.6373	0.9753	0.165*

	U11	U22	U33	U12	U13	U23
N1	0.047 (2)	0.0349 (18)	0.072 (2)	0.0098 (14)	0.037 (2)	0.0113 (15)
N2	0.058 (2)	0.0331 (19)	0.065 (2)	0.0014 (15)	0.0384 (19)	0.0075 (14)
N3	0.053 (2)	0.0363 (18)	0.074 (2)	0.0055 (14)	0.041 (2)	0.0085 (15)
N4	0.056 (2)	0.0355 (19)	0.068 (2)	0.0017 (15)	0.038 (2)	0.0059 (15)
O1	0.0673 (18)	0.0414 (16)	0.088 (2)	0.0067 (13)	0.0563 (18)	0.0067 (14)
O2	0.068 (3)	0.082 (5)	0.086 (4)	−0.010 (4)	0.019 (3)	0.002 (5)
C4'	0.068 (3)	0.082 (5)	0.086 (4)	−0.010 (4)	0.019 (3)	0.002 (5)
O3	0.0712 (19)	0.0502 (17)	0.0654 (18)	−0.0097 (13)	0.0466 (17)	−0.0051 (13)
O4	0.089 (2)	0.0406 (18)	0.097 (2)	−0.0088 (15)	0.061 (2)	−0.0133 (15)
O5	0.0728 (19)	0.0429 (17)	0.091 (2)	0.0006 (14)	0.0604 (19)	0.0001 (14)
O6	0.077 (3)	0.116 (3)	0.105 (3)	−0.018 (2)	0.015 (3)	0.006 (2)
O7	0.083 (2)	0.070 (2)	0.076 (2)	−0.0077 (16)	0.055 (2)	−0.0078 (16)
O8	0.100 (3)	0.052 (2)	0.105 (3)	−0.0020 (17)	0.066 (2)	−0.0134 (17)
C1	0.041 (2)	0.041 (2)	0.064 (3)	0.0000 (17)	0.032 (2)	0.0031 (19)
C2	0.044 (2)	0.037 (2)	0.055 (2)	−0.0022 (17)	0.030 (2)	0.0033 (17)
C3	0.049 (3)	0.041 (2)	0.074 (3)	−0.001 (2)	0.027 (3)	−0.004 (2)
C4	0.058 (3)	0.084 (6)	0.090 (5)	−0.003 (5)	0.031 (4)	−0.011 (5)
C5	0.052 (4)	0.090 (11)	0.100 (9)	−0.006 (8)	0.024 (6)	−0.015 (9)
C6	0.068 (6)	0.081 (14)	0.095 (6)	−0.007 (10)	0.016 (5)	−0.005 (11)
O2'	0.058 (3)	0.084 (6)	0.090 (5)	−0.003 (5)	0.031 (4)	−0.011 (5)
C5'	0.068 (6)	0.081 (14)	0.095 (6)	−0.007 (10)	0.016 (5)	−0.005 (11)
C6'	0.052 (4)	0.090 (11)	0.100 (9)	−0.006 (8)	0.024 (6)	−0.015 (9)
C7	0.043 (2)	0.045 (3)	0.053 (2)	−0.0040 (18)	0.025 (2)	−0.0023 (19)
C8	0.040 (2)	0.033 (2)	0.053 (2)	−0.0022 (16)	0.025 (2)	−0.0002 (16)
C9	0.041 (2)	0.037 (2)	0.057 (2)	−0.0012 (16)	0.029 (2)	−0.0004 (17)
C10	0.079 (3)	0.035 (2)	0.091 (3)	−0.009 (2)	0.055 (3)	−0.005 (2)
C11	0.075 (3)	0.070 (3)	0.071 (3)	−0.005 (2)	0.048 (3)	−0.004 (2)
C12	0.086 (4)	0.094 (4)	0.088 (4)	−0.023 (3)	0.057 (3)	−0.005 (3)
C13	0.044 (2)	0.039 (2)	0.064 (3)	0.0000 (17)	0.029 (2)	0.0050 (18)
C14	0.049 (2)	0.044 (2)	0.059 (3)	0.0016 (18)	0.033 (2)	0.0051 (18)
C15	0.054 (3)	0.049 (3)	0.081 (4)	−0.005 (2)	0.038 (3)	−0.007 (2)
C16	0.077 (4)	0.106 (5)	0.107 (5)	−0.027 (3)	0.054 (4)	−0.013 (3)
C17	0.068 (4)	0.110 (6)	0.161 (7)	−0.021 (4)	0.054 (5)	−0.043 (5)
C18	0.069 (5)	0.127 (6)	0.123 (7)	−0.007 (4)	−0.002 (5)	−0.019 (5)
C19	0.046 (3)	0.059 (3)	0.066 (3)	−0.005 (2)	0.028 (2)	−0.003 (2)
C20	0.038 (2)	0.041 (2)	0.057 (2)	0.0002 (17)	0.022 (2)	−0.0021 (18)
C21	0.038 (2)	0.037 (2)	0.058 (3)	−0.0007 (16)	0.022 (2)	−0.0011 (17)
C22	0.063 (3)	0.039 (2)	0.080 (3)	−0.0017 (19)	0.037 (3)	0.000 (2)
C23	0.103 (4)	0.090 (4)	0.082 (3)	−0.009 (3)	0.065 (3)	−0.013 (3)
C24	0.122 (5)	0.140 (6)	0.106 (4)	−0.030 (4)	0.084 (4)	−0.017 (4)

N1—C1	1.322 (4)	O2'—C6'	1.41 (3)
N1—C2	1.454 (4)	C5'—C6'	1.17 (6)
N1—H1	0.8600	C5'—H5'	0.9300
N2—C1	1.365 (4)	C6'—H6'	0.9300
N2—C9	1.379 (4)	C7—C8	1.462 (5)
N2—H2	0.8600	C8—C9	1.339 (5)
N3—C13	1.343 (5)	C9—C10	1.485 (5)
N3—C14	1.454 (4)	C10—H10A	0.9600
N3—H3	0.8600	C10—H10B	0.9600
N4—C21	1.373 (4)	C10—H10C	0.9600
N4—C13	1.377 (4)	C11—C12	1.496 (6)
N4—H4	0.8600	C11—H11A	0.9700
O1—C1	1.241 (4)	C11—H11B	0.9700
O2—C3	1.263 (8)	C12—H12A	0.9600
O2—C6	1.37 (2)	C12—H12B	0.9600
C4'—C3	1.44 (2)	C12—H12C	0.9600
C4'—C5'	1.50 (5)	C14—C15	1.480 (5)
C4'—H4'	0.9300	C14—C20	1.518 (5)
O3—C7	1.338 (4)	C14—H14	0.9800
O3—C11	1.430 (4)	C15—C16	1.327 (6)
O4—C7	1.211 (4)	C16—C17	1.395 (8)
O5—C13	1.224 (4)	C16—H16	0.9300
O6—C15	1.330 (6)	C17—C18	1.294 (9)
O6—C18	1.387 (7)	C17—H17	0.9300
O7—C19	1.337 (5)	C18—H18	0.9300
O7—C23	1.449 (5)	C19—C20	1.455 (5)
O8—C19	1.201 (4)	C20—C21	1.349 (5)
C2—C3	1.484 (5)	C21—C22	1.494 (5)
C2—C8	1.509 (5)	C22—H22A	0.9600
C2—H2A	0.9800	C22—H22B	0.9600
C3—O2'	1.262 (10)	C22—H22C	0.9600
C3—C4	1.387 (10)	C23—C24	1.458 (7)
C4—C5	1.405 (18)	C23—H23A	0.9700
C4—H4A	0.9300	C23—H23B	0.9700
C5—C6	1.38 (3)	C24—H24A	0.9600
C5—H5	0.9300	C24—H24B	0.9600
C6—H6	0.9300	C24—H24C	0.9600
C1—N1—C2	122.9 (3)	H10A—C10—H10B	109.5
C1—N1—H1	118.6	C9—C10—H10C	109.5
C2—N1—H1	118.6	H10A—C10—H10C	109.5
C1—N2—C9	123.9 (3)	H10B—C10—H10C	109.5
C1—N2—H2	118.0	O3—C11—C12	107.3 (4)
C9—N2—H2	118.0	O3—C11—H11A	110.3
C13—N3—C14	125.2 (3)	C12—C11—H11A	110.3
C13—N3—H3	117.4	O3—C11—H11B	110.3
C14—N3—H3	117.4	C12—C11—H11B	110.3
C21—N4—C13	125.1 (3)	H11A—C11—H11B	108.5
C21—N4—H4	117.5	C11—C12—H12A	109.5
C13—N4—H4	117.5	C11—C12—H12B	109.5
C3—O2—C6	112.1 (12)	H12A—C12—H12B	109.5
C3—C4'—C5'	101 (2)	C11—C12—H12C	109.5
C3—C4'—H4'	129.5	H12A—C12—H12C	109.5
C5'—C4'—H4'	129.5	H12B—C12—H12C	109.5
C7—O3—C11	117.6 (3)	O5—C13—N3	124.2 (4)
C15—O6—C18	106.5 (5)	O5—C13—N4	120.8 (3)
C19—O7—C23	117.0 (4)	N3—C13—N4	115.0 (4)
O1—C1—N1	123.9 (4)	N3—C14—C15	111.5 (3)
O1—C1—N2	120.4 (3)	N3—C14—C20	110.5 (3)
N1—C1—N2	115.6 (3)	C15—C14—C20	112.6 (3)
N1—C2—C3	110.7 (3)	N3—C14—H14	107.3
N1—C2—C8	109.4 (3)	C15—C14—H14	107.3
C3—C2—C8	111.0 (3)	C20—C14—H14	107.3
N1—C2—H2A	108.5	C16—C15—O6	109.7 (5)
C3—C2—H2A	108.5	C16—C15—C14	131.2 (5)
C8—C2—H2A	108.5	O6—C15—C14	119.1 (4)
O2'—C3—O2	87.6 (7)	C15—C16—C17	107.0 (6)
O2'—C3—C4	44.8 (5)	C15—C16—H16	126.5
O2—C3—C4	110.9 (6)	C17—C16—H16	126.5
O2'—C3—C4'	104.6 (10)	C18—C17—C16	107.7 (6)
O2—C3—C4'	35.0 (6)	C18—C17—H17	126.2
C4—C3—C4'	101.9 (9)	C16—C17—H17	126.2
O2'—C3—C2	127.2 (6)	C17—C18—O6	109.1 (7)
O2—C3—C2	120.8 (5)	C17—C18—H18	125.4
C4—C3—C2	127.8 (6)	O6—C18—H18	125.4
C4'—C3—C2	124.4 (9)	O8—C19—O7	121.5 (4)
C3—C4—C5	103.2 (10)	O8—C19—C20	127.3 (4)
C3—C4—H4A	128.4	O7—C19—C20	111.3 (4)
C5—C4—H4A	128.4	C21—C20—C19	121.7 (4)
C6—C5—C4	109.5 (15)	C21—C20—C14	119.5 (3)
C6—C5—H5	125.2	C19—C20—C14	118.8 (3)
C4—C5—H5	125.2	C20—C21—N4	119.7 (3)
O2—C6—C5	104.1 (18)	C20—C21—C22	126.7 (3)
O2—C6—H6	127.9	N4—C21—C22	113.5 (3)
C5—C6—H6	127.9	C21—C22—H22A	109.5
C3—O2'—C6'	113.1 (15)	C21—C22—H22B	109.5
C6'—C5'—C4'	110 (3)	H22A—C22—H22B	109.5
C6'—C5'—H5'	125.2	C21—C22—H22C	109.5
C4'—C5'—H5'	125.2	H22A—C22—H22C	109.5
C5'—C6'—O2'	108 (3)	H22B—C22—H22C	109.5
C5'—C6'—H6'	125.9	O7—C23—C24	107.9 (4)
O2'—C6'—H6'	125.9	O7—C23—H23A	110.1
O4—C7—O3	121.3 (3)	C24—C23—H23A	110.1
O4—C7—C8	127.4 (3)	O7—C23—H23B	110.1
O3—C7—C8	111.2 (3)	C24—C23—H23B	110.1
C9—C8—C7	122.9 (3)	H23A—C23—H23B	108.4
C9—C8—C2	118.2 (3)	C23—C24—H24A	109.5
C7—C8—C2	118.9 (3)	C23—C24—H24B	109.5
C8—C9—N2	119.1 (3)	H24A—C24—H24B	109.5
C8—C9—C10	127.9 (3)	C23—C24—H24C	109.5
N2—C9—C10	113.0 (3)	H24A—C24—H24C	109.5
C9—C10—H10A	109.5	H24B—C24—H24C	109.5
C9—C10—H10B	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	2.12	2.924 (4)	156
N2—H2···O5ii	0.86	2.02	2.851 (4)	162
N3—H3···O4iii	0.86	2.38	3.077 (4)	138
N4—H4···O1iv	0.86	2.10	2.952 (4)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	2.12	2.924 (4)	156
N2—H2⋯O5ii	0.86	2.02	2.851 (4)	162
N3—H3⋯O4iii	0.86	2.38	3.077 (4)	138
N4—H4⋯O1iv	0.86	2.10	2.952 (4)	174

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