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

In the title mol­ecule, C₁₄H₁₆N₂O₄, all bond lengths and angles are normal. The crystal packing is stabilized by inter­molecular O—H...O hydrogen bonds involving the hydr­oxy and keto groups, and by N—H...O hydrogen bonds involving the amino and keto groups.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.048
• wR factor = 0.135
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.58 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.20 Ratio

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000) and DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXTL.

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

Crystal data

C14H16N2O4	F(000) = 1168
Mr = 276.29	Dx = 1.406 Mg m^−3
Monoclinic, C2/c	Melting point: 490 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 20.757 (3) Å	Cell parameters from 1277 reflections
b = 9.042 (2) Å	θ = 2.5–22.2°
c = 13.919 (2) Å	µ = 0.10 mm^−1
β = 92.313 (3)°	T = 298 K
V = 2610.2 (9) Å^3	Prism, white
Z = 8	0.32 × 0.16 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer	2308 independent reflections
Radiation source: fine-focus sealed tube	1363 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.046
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −24→21
Tmin = 0.967, Tmax = 0.987	k = −10→10
6587 measured reflections	l = −14→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0508P)^2 + 2.0298P] where P = (Fo^2 + 2Fc^2)/3
2308 reflections	(Δ/σ)max < 0.001
181 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

Special details

Experimental. Elemental analysis, calculated for C₁₄H₁₆N₂O₄: C 60.86, H 5.84, N 10.14%; found: C 61.13, H 5.74, N 10.21%.

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.07708 (11)	0.6935 (2)	1.11033 (16)	0.0397 (6)
H1	0.0869	0.7010	1.1707	0.048*
N2	0.04431 (10)	0.8044 (2)	0.96781 (16)	0.0385 (6)
H2	0.0207	0.8697	0.9385	0.046*
O1	0.13181 (11)	0.3171 (2)	0.95946 (14)	0.0543 (6)
O2	0.07365 (11)	0.3977 (2)	0.83254 (15)	0.0605 (7)
O3	0.03723 (10)	0.9281 (2)	1.10907 (14)	0.0491 (6)
O4	0.06549 (9)	0.8956 (2)	0.76659 (14)	0.0509 (6)
H4	0.0664	0.9587	0.7243	0.076*
C1	0.09483 (14)	0.4163 (3)	0.9137 (2)	0.0384 (7)
C2	0.08496 (12)	0.5514 (3)	0.96959 (19)	0.0339 (7)
C3	0.08734 (13)	0.5583 (3)	1.06554 (19)	0.0359 (7)
C4	0.05200 (12)	0.8162 (3)	1.0631 (2)	0.0359 (7)
C5	0.07301 (12)	0.6888 (3)	0.90913 (18)	0.0324 (6)
H5	0.0416	0.6632	0.8574	0.039*
C6	0.13346 (12)	0.7449 (3)	0.86283 (19)	0.0330 (7)
C7	0.12675 (14)	0.8508 (3)	0.79024 (19)	0.0376 (7)
C8	0.17964 (16)	0.9065 (3)	0.7466 (2)	0.0501 (8)
H8	0.1745	0.9770	0.6982	0.060*
C9	0.24035 (17)	0.8579 (4)	0.7747 (3)	0.0599 (10)
H9	0.2762	0.8952	0.7448	0.072*
C10	0.24832 (15)	0.7548 (4)	0.8464 (3)	0.0563 (9)
H10	0.2895	0.7227	0.8652	0.068*
C11	0.19527 (13)	0.6986 (3)	0.8904 (2)	0.0430 (8)
H11	0.2009	0.6290	0.9392	0.052*
C12	0.09848 (16)	0.4337 (3)	1.1353 (2)	0.0506 (8)
H12A	0.0859	0.3421	1.1051	0.076*
H12B	0.0733	0.4496	1.1907	0.076*
H12C	0.1434	0.4296	1.1546	0.076*
C13	0.14261 (17)	0.1766 (3)	0.9126 (2)	0.0576 (9)
H13A	0.1633	0.1919	0.8521	0.069*
H13B	0.1019	0.1261	0.8996	0.069*
C14	0.1840 (2)	0.0889 (4)	0.9778 (3)	0.0836 (13)
H14A	0.2229	0.1429	0.9934	0.125*
H14B	0.1946	−0.0027	0.9473	0.125*
H14C	0.1618	0.0688	1.0356	0.125*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0515 (15)	0.0381 (14)	0.0292 (13)	0.0083 (12)	−0.0024 (11)	−0.0034 (11)
N2	0.0480 (14)	0.0361 (14)	0.0317 (14)	0.0115 (11)	0.0044 (11)	−0.0001 (11)
O1	0.0826 (16)	0.0335 (12)	0.0459 (13)	0.0172 (11)	−0.0091 (11)	−0.0100 (10)
O2	0.1005 (18)	0.0426 (13)	0.0374 (13)	0.0055 (12)	−0.0081 (12)	−0.0054 (10)
O3	0.0637 (13)	0.0392 (12)	0.0446 (13)	0.0117 (10)	0.0053 (10)	−0.0118 (10)
O4	0.0513 (13)	0.0526 (14)	0.0483 (13)	0.0072 (10)	−0.0043 (10)	0.0173 (11)
C1	0.0532 (18)	0.0333 (17)	0.0289 (16)	−0.0052 (14)	0.0021 (13)	0.0028 (13)
C2	0.0418 (16)	0.0278 (16)	0.0323 (16)	0.0005 (12)	0.0051 (12)	−0.0004 (12)
C3	0.0435 (17)	0.0317 (16)	0.0326 (16)	0.0001 (13)	0.0035 (12)	−0.0002 (13)
C4	0.0357 (16)	0.0346 (17)	0.0379 (17)	0.0012 (13)	0.0052 (13)	−0.0009 (14)
C5	0.0407 (16)	0.0270 (15)	0.0294 (15)	0.0027 (12)	0.0014 (12)	−0.0012 (12)
C6	0.0385 (16)	0.0262 (15)	0.0345 (16)	0.0013 (12)	0.0052 (12)	−0.0056 (12)
C7	0.0495 (18)	0.0333 (17)	0.0300 (16)	−0.0019 (14)	0.0031 (13)	−0.0031 (13)
C8	0.065 (2)	0.045 (2)	0.0409 (18)	−0.0131 (17)	0.0139 (16)	0.0016 (15)
C9	0.057 (2)	0.055 (2)	0.069 (3)	−0.0129 (18)	0.0283 (18)	−0.013 (2)
C10	0.0410 (19)	0.052 (2)	0.077 (3)	0.0036 (16)	0.0092 (17)	−0.013 (2)
C11	0.0441 (18)	0.0335 (17)	0.051 (2)	0.0031 (14)	−0.0004 (15)	−0.0038 (14)
C12	0.076 (2)	0.0385 (19)	0.0371 (18)	0.0014 (16)	0.0052 (15)	0.0054 (15)
C13	0.089 (3)	0.0302 (18)	0.054 (2)	0.0091 (17)	0.0035 (18)	−0.0113 (16)
C14	0.119 (3)	0.045 (2)	0.084 (3)	0.023 (2)	−0.026 (2)	−0.017 (2)

Geometric parameters (Å, º)

N1—C4	1.381 (3)	C6—C7	1.395 (4)
N1—C3	1.392 (3)	C7—C8	1.372 (4)
N1—H1	0.8600	C8—C9	1.376 (4)
N2—C4	1.334 (3)	C8—H8	0.9300
N2—C5	1.468 (3)	C9—C10	1.371 (5)
N2—H2	0.8600	C9—H9	0.9300
O1—C1	1.326 (3)	C10—C11	1.379 (4)
O1—C13	1.450 (3)	C10—H10	0.9300
O2—C1	1.208 (3)	C11—H11	0.9300
O3—C4	1.242 (3)	C12—H12A	0.9600
O4—C7	1.362 (3)	C12—H12B	0.9600
O4—H4	0.8200	C12—H12C	0.9600
C1—C2	1.467 (4)	C13—C14	1.459 (4)
C2—C3	1.336 (4)	C13—H13A	0.9700
C2—C5	1.515 (3)	C13—H13B	0.9700
C3—C12	1.499 (4)	C14—H14A	0.9600
C5—C6	1.521 (4)	C14—H14B	0.9600
C5—H5	0.9800	C14—H14C	0.9600
C6—C11	1.389 (4)
C4—N1—C3	123.6 (2)	C8—C7—C6	121.0 (3)
C4—N1—H1	118.2	C7—C8—C9	119.8 (3)
C3—N1—H1	118.2	C7—C8—H8	120.1
C4—N2—C5	125.1 (2)	C9—C8—H8	120.1
C4—N2—H2	117.4	C10—C9—C8	120.4 (3)
C5—N2—H2	117.4	C10—C9—H9	119.8
C1—O1—C13	118.3 (2)	C8—C9—H9	119.8
C7—O4—H4	109.5	C9—C10—C11	120.0 (3)
O2—C1—O1	122.4 (3)	C9—C10—H10	120.0
O2—C1—C2	124.0 (3)	C11—C10—H10	120.0
O1—C1—C2	113.5 (2)	C10—C11—C6	120.7 (3)
C3—C2—C1	124.7 (2)	C10—C11—H11	119.6
C3—C2—C5	121.0 (2)	C6—C11—H11	119.6
C1—C2—C5	114.3 (2)	C3—C12—H12A	109.5
C2—C3—N1	119.3 (2)	C3—C12—H12B	109.5
C2—C3—C12	127.6 (3)	H12A—C12—H12B	109.5
N1—C3—C12	113.1 (2)	C3—C12—H12C	109.5
O3—C4—N2	123.7 (3)	H12A—C12—H12C	109.5
O3—C4—N1	120.3 (3)	H12B—C12—H12C	109.5
N2—C4—N1	115.9 (2)	O1—C13—C14	107.1 (3)
N2—C5—C2	109.6 (2)	O1—C13—H13A	110.3
N2—C5—C6	111.0 (2)	C14—C13—H13A	110.3
C2—C5—C6	112.9 (2)	O1—C13—H13B	110.3
N2—C5—H5	107.7	C14—C13—H13B	110.3
C2—C5—H5	107.7	H13A—C13—H13B	108.5
C6—C5—H5	107.7	C13—C14—H14A	109.5
C11—C6—C7	118.1 (3)	C13—C14—H14B	109.5
C11—C6—C5	123.4 (2)	H14A—C14—H14B	109.5
C7—C6—C5	118.4 (2)	C13—C14—H14C	109.5
O4—C7—C8	122.6 (3)	H14A—C14—H14C	109.5
O4—C7—C6	116.4 (2)	H14B—C14—H14C	109.5
C13—O1—C1—O2	−5.1 (4)	C1—C2—C5—N2	162.4 (2)
C13—O1—C1—C2	177.5 (3)	C3—C2—C5—C6	105.4 (3)
O2—C1—C2—C3	155.7 (3)	C1—C2—C5—C6	−73.2 (3)
O1—C1—C2—C3	−26.9 (4)	N2—C5—C6—C11	109.1 (3)
O2—C1—C2—C5	−25.8 (4)	C2—C5—C6—C11	−14.5 (4)
O1—C1—C2—C5	151.6 (2)	N2—C5—C6—C7	−69.5 (3)
C1—C2—C3—N1	−180.0 (2)	C2—C5—C6—C7	166.9 (2)
C5—C2—C3—N1	1.6 (4)	C11—C6—C7—O4	−178.7 (2)
C1—C2—C3—C12	−1.7 (5)	C5—C6—C7—O4	0.0 (4)
C5—C2—C3—C12	179.9 (3)	C11—C6—C7—C8	0.7 (4)
C4—N1—C3—C2	13.4 (4)	C5—C6—C7—C8	179.3 (2)
C4—N1—C3—C12	−165.1 (2)	O4—C7—C8—C9	179.2 (3)
C5—N2—C4—O3	166.5 (2)	C6—C7—C8—C9	−0.1 (4)
C5—N2—C4—N1	−14.4 (4)	C7—C8—C9—C10	−0.4 (5)
C3—N1—C4—O3	171.8 (2)	C8—C9—C10—C11	0.3 (5)
C3—N1—C4—N2	−7.3 (4)	C9—C10—C11—C6	0.3 (5)
C4—N2—C5—C2	26.4 (3)	C7—C6—C11—C10	−0.7 (4)
C4—N2—C5—C6	−99.1 (3)	C5—C6—C11—C10	−179.3 (3)
C3—C2—C5—N2	−19.0 (3)	C1—O1—C13—C14	−179.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	2.45	3.205 (5)	147
N2—H2···O3^ii	0.86	2.27	3.117 (4)	167
O4—H4···O3^iii	0.82	1.98	2.755 (4)	158

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