Ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate: a triclinic polymorph

The title compound, C₁₂H₁₄N₂O₄, crystallizes in the triclinic space group P-1. The previously reported polymorph occurs in the monoclinic space group P2₁/c, and has two independent mol­ecules in the asymmetric unit [Wang (2010). Acta Cryst. E66, o2822]. The di­hydro­pyrimidine ring adopts a screw-boat conformation. The furan ring is positioned axially and makes a dihedral angle of 85.94 (7)° with the mean plane through the pyrimidine ring. In the crystal, mol­ecules are linked via pairs of N—H...O hydrogen bonds, forming inversion dimers with an R₂²(8) ring motif. The dimers are linked by N—H...O and C—H...O hydrogen bonds, forming chains propagating along the a-axis direction.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.042
• wR factor = 0.123
• Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT031_ALERT_4_B Refined Extinction Parameter within Range ......      2.000 Sigma

Alert level C
PLAT242_ALERT_2_C Low    'MainMol' Ueq as Compared to Neighbors of         C9 Check
PLAT397_ALERT_2_C Deviating  C-O-C  Angle from 120 Deg for  O4          106.8 Degree

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details found  in the CIF     Please Do !
PLAT007_ALERT_5_G Number of Unrefined Donor-H Atoms ..............          2 Report
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.002 Degree
PLAT793_ALERT_4_G The Model has Chirality at C4      (Centro SPGR)          S Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          3 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Ethyl 4-(furan-2-yl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate

Crystal data

C12H14N2O4	Z = 2
Mr = 250.25	F(000) = 264
Triclinic, P1	Dx = 1.373 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4670 (2) Å	Cell parameters from 2458 reflections
b = 8.8307 (3) Å	θ = 2.2–26.3°
c = 10.5426 (3) Å	µ = 0.10 mm^−1
α = 106.833 (2)°	T = 296 K
β = 108.557 (2)°	Block, colourless
γ = 99.420 (2)°	0.19 × 0.16 × 0.13 mm
V = 605.20 (3) Å^3

Data collection

Bruker Kappa APEXII CCD diffractometer	2458 independent reflections
Radiation source: fine-focus sealed tube	2116 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
ω and φ scan	θmax = 26.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −9→9
Tmin = 0.980, Tmax = 0.987	k = −10→10
9061 measured reflections	l = −13→12

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.042	H-atom parameters constrained
wR(F^2) = 0.123	w = 1/[σ^2(Fo^2) + (0.0596P)^2 + 0.1739P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max < 0.001
2458 reflections	Δρmax = 0.31 e Å^−3
166 parameters	Δρmin = −0.36 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.010 (5)

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O4	0.7408 (2)	0.90463 (16)	0.92870 (14)	0.0670 (4)
C10	0.5796 (3)	0.7209 (3)	0.9849 (2)	0.0647 (5)
H10	0.5005	0.6241	0.9791	0.078*
C11	0.6772 (3)	0.8695 (3)	1.1090 (2)	0.0699 (6)
H11	0.6753	0.8875	1.1999	0.084*
C12	0.7690 (3)	0.9745 (3)	1.0699 (2)	0.0725 (6)
H12	0.8433	1.0821	1.1296	0.087*
O1	0.32040 (15)	0.90923 (14)	0.55610 (13)	0.0463 (3)
N2	0.60593 (17)	0.84873 (15)	0.56522 (14)	0.0391 (3)
H2	0.6340	0.9242	0.5326	0.047*
O2	1.01790 (16)	0.58238 (15)	0.69053 (14)	0.0529 (3)
C3	0.71862 (19)	0.65870 (17)	0.66569 (15)	0.0346 (3)
O3	0.79382 (16)	0.45399 (13)	0.75180 (13)	0.0474 (3)
C6	0.8590 (2)	0.56456 (18)	0.70103 (16)	0.0378 (3)
N1	0.39886 (17)	0.70961 (15)	0.64088 (13)	0.0384 (3)
H1	0.2789	0.6658	0.6263	0.046*
C1	0.4345 (2)	0.82776 (18)	0.58816 (15)	0.0354 (3)
C2	0.73651 (19)	0.75677 (17)	0.59092 (15)	0.0350 (3)
C4	0.5541 (2)	0.65133 (17)	0.72213 (16)	0.0354 (3)
H4	0.4969	0.5358	0.7054	0.042*
C9	0.6239 (2)	0.74810 (18)	0.87951 (16)	0.0388 (3)
C7	0.9206 (3)	0.3533 (2)	0.7928 (2)	0.0510 (4)
H7A	1.0495	0.4230	0.8629	0.061*
H7B	0.9365	0.2840	0.7093	0.061*
C5	0.8859 (2)	0.7784 (2)	0.52603 (19)	0.0501 (4)
H5A	1.0055	0.8581	0.5979	0.075*
H5B	0.8361	0.8162	0.4486	0.075*
H5C	0.9118	0.6749	0.4900	0.075*
C8	0.8261 (4)	0.2502 (3)	0.8552 (3)	0.0700 (6)
H8A	0.8160	0.3200	0.9399	0.105*
H8B	0.9041	0.1790	0.8801	0.105*
H8C	0.6969	0.1848	0.7861	0.105*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O4	0.0817 (9)	0.0548 (8)	0.0514 (7)	−0.0049 (7)	0.0300 (7)	0.0097 (6)
C10	0.0792 (13)	0.0694 (12)	0.0645 (12)	0.0188 (10)	0.0445 (11)	0.0339 (10)
C11	0.0797 (14)	0.0946 (16)	0.0453 (10)	0.0336 (12)	0.0338 (10)	0.0241 (10)
C12	0.0817 (14)	0.0704 (13)	0.0480 (10)	0.0099 (11)	0.0246 (10)	0.0043 (9)
O1	0.0360 (6)	0.0589 (7)	0.0635 (7)	0.0228 (5)	0.0282 (5)	0.0348 (6)
N2	0.0326 (6)	0.0449 (7)	0.0532 (7)	0.0143 (5)	0.0248 (5)	0.0260 (6)
O2	0.0403 (6)	0.0607 (7)	0.0782 (8)	0.0246 (5)	0.0336 (6)	0.0363 (6)
C3	0.0303 (7)	0.0343 (7)	0.0405 (7)	0.0091 (5)	0.0179 (6)	0.0110 (6)
O3	0.0455 (6)	0.0469 (6)	0.0666 (7)	0.0214 (5)	0.0303 (5)	0.0300 (6)
C6	0.0362 (7)	0.0360 (7)	0.0431 (8)	0.0109 (6)	0.0196 (6)	0.0121 (6)
N1	0.0261 (6)	0.0458 (7)	0.0495 (7)	0.0094 (5)	0.0190 (5)	0.0215 (6)
C1	0.0292 (6)	0.0404 (7)	0.0383 (7)	0.0100 (6)	0.0157 (5)	0.0138 (6)
C2	0.0292 (7)	0.0371 (7)	0.0399 (7)	0.0091 (6)	0.0171 (6)	0.0116 (6)
C4	0.0320 (7)	0.0342 (7)	0.0470 (8)	0.0105 (5)	0.0211 (6)	0.0177 (6)
C9	0.0370 (7)	0.0426 (8)	0.0473 (8)	0.0155 (6)	0.0229 (6)	0.0214 (6)
C7	0.0530 (9)	0.0506 (9)	0.0620 (10)	0.0262 (8)	0.0265 (8)	0.0274 (8)
C5	0.0438 (9)	0.0659 (11)	0.0649 (10)	0.0250 (8)	0.0362 (8)	0.0357 (9)
C8	0.0852 (15)	0.0629 (12)	0.0862 (14)	0.0319 (11)	0.0446 (12)	0.0428 (11)

Geometric parameters (Å, º)

O4—C9	1.3575 (19)	O3—C7	1.4528 (19)
O4—C12	1.366 (2)	N1—C1	1.3444 (19)
C10—C9	1.328 (2)	N1—C4	1.4702 (18)
C10—C11	1.432 (3)	N1—H1	0.8600
C10—H10	0.9300	C2—C5	1.4967 (19)
C11—C12	1.301 (3)	C4—C9	1.496 (2)
C11—H11	0.9300	C4—H4	0.9800
C12—H12	0.9300	C7—C8	1.481 (3)
O1—C1	1.2312 (17)	C7—H7A	0.9700
N2—C1	1.3700 (17)	C7—H7B	0.9700
N2—C2	1.3791 (18)	C5—H5A	0.9600
N2—H2	0.8600	C5—H5B	0.9600
O2—C6	1.2152 (18)	C5—H5C	0.9600
C3—C2	1.347 (2)	C8—H8A	0.9600
C3—C6	1.465 (2)	C8—H8B	0.9600
C3—C4	1.5258 (18)	C8—H8C	0.9600
O3—C6	1.3378 (18)
C9—O4—C12	106.82 (15)	N2—C2—C5	112.94 (12)
C9—C10—C11	106.66 (18)	N1—C4—C9	109.89 (11)
C9—C10—H10	126.7	N1—C4—C3	109.59 (11)
C11—C10—H10	126.7	C9—C4—C3	113.30 (11)
C12—C11—C10	106.67 (17)	N1—C4—H4	108.0
C12—C11—H11	126.7	C9—C4—H4	108.0
C10—C11—H11	126.7	C3—C4—H4	108.0
C11—C12—O4	110.45 (19)	C10—C9—O4	109.38 (15)
C11—C12—H12	124.8	C10—C9—C4	133.32 (16)
O4—C12—H12	124.8	O4—C9—C4	116.85 (12)
C1—N2—C2	124.35 (12)	O3—C7—C8	107.47 (15)
C1—N2—H2	117.8	O3—C7—H7A	110.2
C2—N2—H2	117.8	C8—C7—H7A	110.2
C2—C3—C6	121.82 (12)	O3—C7—H7B	110.2
C2—C3—C4	119.48 (12)	C8—C7—H7B	110.2
C6—C3—C4	118.62 (12)	H7A—C7—H7B	108.5
C6—O3—C7	117.05 (12)	C2—C5—H5A	109.5
O2—C6—O3	122.08 (14)	C2—C5—H5B	109.5
O2—C6—C3	126.50 (14)	H5A—C5—H5B	109.5
O3—C6—C3	111.41 (12)	C2—C5—H5C	109.5
C1—N1—C4	123.44 (11)	H5A—C5—H5C	109.5
C1—N1—H1	118.3	H5B—C5—H5C	109.5
C4—N1—H1	118.3	C7—C8—H8A	109.5
O1—C1—N1	123.84 (12)	C7—C8—H8B	109.5
O1—C1—N2	120.65 (13)	H8A—C8—H8B	109.5
N1—C1—N2	115.45 (12)	C7—C8—H8C	109.5
C3—C2—N2	119.95 (12)	H8A—C8—H8C	109.5
C3—C2—C5	127.10 (13)	H8B—C8—H8C	109.5
C9—C10—C11—C12	1.0 (3)	C1—N2—C2—C3	−12.1 (2)
C10—C11—C12—O4	−0.8 (3)	C1—N2—C2—C5	166.89 (14)
C9—O4—C12—C11	0.3 (3)	C1—N1—C4—C9	91.93 (16)
C7—O3—C6—O2	−0.7 (2)	C1—N1—C4—C3	−33.18 (18)
C7—O3—C6—C3	−179.29 (12)	C2—C3—C4—N1	20.23 (18)
C2—C3—C6—O2	12.9 (2)	C6—C3—C4—N1	−162.82 (12)
C4—C3—C6—O2	−163.98 (15)	C2—C3—C4—C9	−102.90 (15)
C2—C3—C6—O3	−168.65 (13)	C6—C3—C4—C9	74.05 (16)
C4—C3—C6—O3	14.48 (18)	C11—C10—C9—O4	−0.8 (2)
C4—N1—C1—O1	−159.14 (14)	C11—C10—C9—C4	−172.63 (17)
C4—N1—C1—N2	23.7 (2)	C12—O4—C9—C10	0.3 (2)
C2—N2—C1—O1	−176.44 (13)	C12—O4—C9—C4	173.67 (15)
C2—N2—C1—N1	0.8 (2)	N1—C4—C9—C10	96.8 (2)
C6—C3—C2—N2	−177.23 (12)	C3—C4—C9—C10	−140.24 (19)
C4—C3—C2—N2	−0.4 (2)	N1—C4—C9—O4	−74.56 (16)
C6—C3—C2—C5	4.0 (2)	C3—C4—C9—O4	48.40 (18)
C4—C3—C2—C5	−179.20 (14)	C6—O3—C7—C8	175.87 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.86	2.00	2.855 (2)	176
N1—H1···O2^ii	0.86	2.34	3.142 (2)	156
C5—H5A···O1^iii	0.96	2.52	3.141 (2)	122

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y, z; (iii) x+1, y, z.