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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015826/cv2225sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015826/cv2225Isup2.hkl
Contains datablock I

CCDC reference: 647178

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

Computing details top

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 top
Crystal data top
C14H16N2O4F(000) = 1168
Mr = 276.29Dx = 1.406 Mg m3
Monoclinic, C2/cMelting point: 490 K
Hall symbol: -C 2ycMo Kα radiation, λ = 0.71073 Å
a = 20.757 (3) ÅCell parameters from 1277 reflections
b = 9.042 (2) Åθ = 2.5–22.2°
c = 13.919 (2) ŵ = 0.10 mm1
β = 92.313 (3)°T = 298 K
V = 2610.2 (9) Å3Prism, white
Z = 80.32 × 0.16 × 0.13 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
2308 independent reflections
Radiation source: fine-focus sealed tube1363 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
φ and ω scansθmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2421
Tmin = 0.967, Tmax = 0.987k = 1010
6587 measured reflectionsl = 1416
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0508P)2 + 2.0298P]
where P = (Fo2 + 2Fc2)/3
2308 reflections(Δ/σ)max < 0.001
181 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.22 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.07708 (11)0.6935 (2)1.11033 (16)0.0397 (6)
H10.08690.70101.17070.048*
N20.04431 (10)0.8044 (2)0.96781 (16)0.0385 (6)
H20.02070.86970.93850.046*
O10.13181 (11)0.3171 (2)0.95946 (14)0.0543 (6)
O20.07365 (11)0.3977 (2)0.83254 (15)0.0605 (7)
O30.03723 (10)0.9281 (2)1.10907 (14)0.0491 (6)
O40.06549 (9)0.8956 (2)0.76659 (14)0.0509 (6)
H40.06640.95870.72430.076*
C10.09483 (14)0.4163 (3)0.9137 (2)0.0384 (7)
C20.08496 (12)0.5514 (3)0.96959 (19)0.0339 (7)
C30.08734 (13)0.5583 (3)1.06554 (19)0.0359 (7)
C40.05200 (12)0.8162 (3)1.0631 (2)0.0359 (7)
C50.07301 (12)0.6888 (3)0.90913 (18)0.0324 (6)
H50.04160.66320.85740.039*
C60.13346 (12)0.7449 (3)0.86283 (19)0.0330 (7)
C70.12675 (14)0.8508 (3)0.79024 (19)0.0376 (7)
C80.17964 (16)0.9065 (3)0.7466 (2)0.0501 (8)
H80.17450.97700.69820.060*
C90.24035 (17)0.8579 (4)0.7747 (3)0.0599 (10)
H90.27620.89520.74480.072*
C100.24832 (15)0.7548 (4)0.8464 (3)0.0563 (9)
H100.28950.72270.86520.068*
C110.19527 (13)0.6986 (3)0.8904 (2)0.0430 (8)
H110.20090.62900.93920.052*
C120.09848 (16)0.4337 (3)1.1353 (2)0.0506 (8)
H12A0.08590.34211.10510.076*
H12B0.07330.44961.19070.076*
H12C0.14340.42961.15460.076*
C130.14261 (17)0.1766 (3)0.9126 (2)0.0576 (9)
H13A0.16330.19190.85210.069*
H13B0.10190.12610.89960.069*
C140.1840 (2)0.0889 (4)0.9778 (3)0.0836 (13)
H14A0.22290.14290.99340.125*
H14B0.19460.00270.94730.125*
H14C0.16180.06881.03560.125*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0515 (15)0.0381 (14)0.0292 (13)0.0083 (12)0.0024 (11)0.0034 (11)
N20.0480 (14)0.0361 (14)0.0317 (14)0.0115 (11)0.0044 (11)0.0001 (11)
O10.0826 (16)0.0335 (12)0.0459 (13)0.0172 (11)0.0091 (11)0.0100 (10)
O20.1005 (18)0.0426 (13)0.0374 (13)0.0055 (12)0.0081 (12)0.0054 (10)
O30.0637 (13)0.0392 (12)0.0446 (13)0.0117 (10)0.0053 (10)0.0118 (10)
O40.0513 (13)0.0526 (14)0.0483 (13)0.0072 (10)0.0043 (10)0.0173 (11)
C10.0532 (18)0.0333 (17)0.0289 (16)0.0052 (14)0.0021 (13)0.0028 (13)
C20.0418 (16)0.0278 (16)0.0323 (16)0.0005 (12)0.0051 (12)0.0004 (12)
C30.0435 (17)0.0317 (16)0.0326 (16)0.0001 (13)0.0035 (12)0.0002 (13)
C40.0357 (16)0.0346 (17)0.0379 (17)0.0012 (13)0.0052 (13)0.0009 (14)
C50.0407 (16)0.0270 (15)0.0294 (15)0.0027 (12)0.0014 (12)0.0012 (12)
C60.0385 (16)0.0262 (15)0.0345 (16)0.0013 (12)0.0052 (12)0.0056 (12)
C70.0495 (18)0.0333 (17)0.0300 (16)0.0019 (14)0.0031 (13)0.0031 (13)
C80.065 (2)0.045 (2)0.0409 (18)0.0131 (17)0.0139 (16)0.0016 (15)
C90.057 (2)0.055 (2)0.069 (3)0.0129 (18)0.0283 (18)0.013 (2)
C100.0410 (19)0.052 (2)0.077 (3)0.0036 (16)0.0092 (17)0.013 (2)
C110.0441 (18)0.0335 (17)0.051 (2)0.0031 (14)0.0004 (15)0.0038 (14)
C120.076 (2)0.0385 (19)0.0371 (18)0.0014 (16)0.0052 (15)0.0054 (15)
C130.089 (3)0.0302 (18)0.054 (2)0.0091 (17)0.0035 (18)0.0113 (16)
C140.119 (3)0.045 (2)0.084 (3)0.023 (2)0.026 (2)0.017 (2)
Geometric parameters (Å, º) top
N1—C41.381 (3)C6—C71.395 (4)
N1—C31.392 (3)C7—C81.372 (4)
N1—H10.8600C8—C91.376 (4)
N2—C41.334 (3)C8—H80.9300
N2—C51.468 (3)C9—C101.371 (5)
N2—H20.8600C9—H90.9300
O1—C11.326 (3)C10—C111.379 (4)
O1—C131.450 (3)C10—H100.9300
O2—C11.208 (3)C11—H110.9300
O3—C41.242 (3)C12—H12A0.9600
O4—C71.362 (3)C12—H12B0.9600
O4—H40.8200C12—H12C0.9600
C1—C21.467 (4)C13—C141.459 (4)
C2—C31.336 (4)C13—H13A0.9700
C2—C51.515 (3)C13—H13B0.9700
C3—C121.499 (4)C14—H14A0.9600
C5—C61.521 (4)C14—H14B0.9600
C5—H50.9800C14—H14C0.9600
C6—C111.389 (4)
C4—N1—C3123.6 (2)C8—C7—C6121.0 (3)
C4—N1—H1118.2C7—C8—C9119.8 (3)
C3—N1—H1118.2C7—C8—H8120.1
C4—N2—C5125.1 (2)C9—C8—H8120.1
C4—N2—H2117.4C10—C9—C8120.4 (3)
C5—N2—H2117.4C10—C9—H9119.8
C1—O1—C13118.3 (2)C8—C9—H9119.8
C7—O4—H4109.5C9—C10—C11120.0 (3)
O2—C1—O1122.4 (3)C9—C10—H10120.0
O2—C1—C2124.0 (3)C11—C10—H10120.0
O1—C1—C2113.5 (2)C10—C11—C6120.7 (3)
C3—C2—C1124.7 (2)C10—C11—H11119.6
C3—C2—C5121.0 (2)C6—C11—H11119.6
C1—C2—C5114.3 (2)C3—C12—H12A109.5
C2—C3—N1119.3 (2)C3—C12—H12B109.5
C2—C3—C12127.6 (3)H12A—C12—H12B109.5
N1—C3—C12113.1 (2)C3—C12—H12C109.5
O3—C4—N2123.7 (3)H12A—C12—H12C109.5
O3—C4—N1120.3 (3)H12B—C12—H12C109.5
N2—C4—N1115.9 (2)O1—C13—C14107.1 (3)
N2—C5—C2109.6 (2)O1—C13—H13A110.3
N2—C5—C6111.0 (2)C14—C13—H13A110.3
C2—C5—C6112.9 (2)O1—C13—H13B110.3
N2—C5—H5107.7C14—C13—H13B110.3
C2—C5—H5107.7H13A—C13—H13B108.5
C6—C5—H5107.7C13—C14—H14A109.5
C11—C6—C7118.1 (3)C13—C14—H14B109.5
C11—C6—C5123.4 (2)H14A—C14—H14B109.5
C7—C6—C5118.4 (2)C13—C14—H14C109.5
O4—C7—C8122.6 (3)H14A—C14—H14C109.5
O4—C7—C6116.4 (2)H14B—C14—H14C109.5
C13—O1—C1—O25.1 (4)C1—C2—C5—N2162.4 (2)
C13—O1—C1—C2177.5 (3)C3—C2—C5—C6105.4 (3)
O2—C1—C2—C3155.7 (3)C1—C2—C5—C673.2 (3)
O1—C1—C2—C326.9 (4)N2—C5—C6—C11109.1 (3)
O2—C1—C2—C525.8 (4)C2—C5—C6—C1114.5 (4)
O1—C1—C2—C5151.6 (2)N2—C5—C6—C769.5 (3)
C1—C2—C3—N1180.0 (2)C2—C5—C6—C7166.9 (2)
C5—C2—C3—N11.6 (4)C11—C6—C7—O4178.7 (2)
C1—C2—C3—C121.7 (5)C5—C6—C7—O40.0 (4)
C5—C2—C3—C12179.9 (3)C11—C6—C7—C80.7 (4)
C4—N1—C3—C213.4 (4)C5—C6—C7—C8179.3 (2)
C4—N1—C3—C12165.1 (2)O4—C7—C8—C9179.2 (3)
C5—N2—C4—O3166.5 (2)C6—C7—C8—C90.1 (4)
C5—N2—C4—N114.4 (4)C7—C8—C9—C100.4 (5)
C3—N1—C4—O3171.8 (2)C8—C9—C10—C110.3 (5)
C3—N1—C4—N27.3 (4)C9—C10—C11—C60.3 (5)
C4—N2—C5—C226.4 (3)C7—C6—C11—C100.7 (4)
C4—N2—C5—C699.1 (3)C5—C6—C11—C10179.3 (3)
C3—C2—C5—N219.0 (3)C1—O1—C13—C14179.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.453.205 (5)147
N2—H2···O3ii0.862.273.117 (4)167
O4—H4···O3iii0.821.982.755 (4)158
Symmetry codes: (i) x, y+1, z+1/2; (ii) x, y+2, z+2; (iii) x, y+2, z1/2.
 

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