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The solid-state structure of the title compound, C14H16N2O4, is characterized by hydrogen-bonding inter­actions, linking the mol­ecules into chains. Hydrogen-bonding inter­actions between neighbouring chains form a two-dimensional network.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008609/bt2027sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008609/bt2027Isup2.hkl
Contains datablock I

CCDC reference: 604984

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C)= 0.003 Å
  • R factor = 0.052
  • wR factor = 0.139
  • Data-to-parameter ratio = 12.7

checkCIF/PLATON results

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No errors found in this datablock

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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, 2002); software used to prepare material for publication: SHELXL97.

Methyl 4-(3-methoxyphenyl)-6-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate top
Crystal data top
C14H16N2O4Z = 2
Mr = 276.29F(000) = 292
Triclinic, P1Dx = 1.385 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.5344 (8) ÅCell parameters from 1648 reflections
b = 7.5833 (8) Åθ = 2.5–25.0°
c = 12.8025 (14) ŵ = 0.10 mm1
α = 78.355 (2)°T = 298 K
β = 81.757 (2)°Block, colourless
γ = 68.040 (2)°0.33 × 0.25 × 0.18 mm
V = 662.58 (12) Å3
Data collection top
Bruker APEX area-detector
diffractometer
2336 independent reflections
Radiation source: fine-focus sealed tube2127 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.010
φ and ω scansθmax = 25.2°, θmin = 1.6°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 89
Tmin = 0.957, Tmax = 0.972k = 89
3528 measured reflectionsl = 1511
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)] = 0.052Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0662P)2 + 0.2894P]
where P = (Fo2 + 2Fc2)/3
2336 reflections(Δ/σ)max = 0.011
184 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.24 e Å3
Special details top

Experimental. 1H NMR (DMSO-d): δ 9.23 (s, 1H), 7.76 (s, 1H), 7.26–7.22 (m, 1H), 6.83–6.78 (m, 3H), 5.13 (s, 1H), 3.73 (s, 3H), 3.54 (s, 3H), 2.25 (s, 3H). 13C NMR (DMSO-d): δ 165.8, 159.3, 152.2, 148.8, 146.1, 129.6, 118.1, 112.4, 112.1, 98.8, 54.9, 53.6, 50.8, 17.8.

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
O10.8170 (3)0.7165 (3)0.97905 (13)0.0680 (5)
O20.7390 (2)0.3231 (2)0.71684 (13)0.0515 (4)
O30.5366 (2)0.2050 (2)0.67149 (15)0.0642 (5)
O40.1717 (2)1.09724 (19)0.51696 (12)0.0470 (4)
N10.4254 (2)0.8841 (2)0.60549 (13)0.0396 (4)
H10.47860.96950.59380.047*
N20.1834 (2)0.7904 (2)0.57488 (13)0.0401 (4)
H20.06700.82210.55930.048*
C10.8186 (4)0.7024 (4)1.09177 (19)0.0721 (8)
H1A0.73290.82101.11390.108*
H1B0.94620.67801.10930.108*
H1C0.77770.59871.12800.108*
C20.6514 (3)0.7290 (3)0.94125 (17)0.0466 (5)
C30.6660 (3)0.7093 (3)0.83413 (15)0.0407 (5)
H30.78300.68980.79420.049*
C40.5092 (3)0.7186 (2)0.78689 (15)0.0344 (4)
C50.3345 (3)0.7490 (3)0.84709 (17)0.0452 (5)
H50.22710.75630.81610.054*
C60.3215 (3)0.7683 (3)0.95278 (18)0.0572 (6)
H60.20450.78820.99280.069*
C70.4787 (4)0.7587 (3)1.00058 (17)0.0543 (6)
H70.46780.77221.07210.065*
C80.5282 (3)0.6985 (3)0.66926 (14)0.0341 (4)
H80.66450.66050.64450.041*
C90.2578 (3)0.9339 (3)0.56371 (15)0.0366 (4)
C100.2845 (3)0.5984 (3)0.60953 (14)0.0351 (4)
C110.4550 (3)0.5465 (3)0.65054 (14)0.0351 (4)
C120.1846 (3)0.4686 (3)0.59577 (19)0.0486 (5)
H12A0.25230.39600.53980.073*
H12B0.05580.54450.57730.073*
H12C0.18140.38190.66140.073*
C130.5743 (3)0.3433 (3)0.67917 (15)0.0393 (5)
C140.8675 (3)0.1284 (3)0.7474 (2)0.0595 (6)
H14A0.81390.06950.81110.089*
H14B0.98910.12980.76070.089*
H14C0.88510.05620.69080.089*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0711 (11)0.1001 (14)0.0448 (9)0.0377 (10)0.0183 (8)0.0142 (9)
O20.0454 (8)0.0380 (8)0.0694 (10)0.0068 (6)0.0182 (7)0.0108 (7)
O30.0688 (11)0.0346 (8)0.0940 (13)0.0172 (8)0.0273 (9)0.0088 (8)
O40.0485 (8)0.0334 (7)0.0618 (9)0.0168 (6)0.0214 (7)0.0028 (6)
N10.0447 (9)0.0368 (9)0.0439 (9)0.0234 (7)0.0148 (7)0.0043 (7)
N20.0373 (9)0.0343 (9)0.0535 (10)0.0160 (7)0.0139 (7)0.0041 (7)
C10.099 (2)0.0849 (19)0.0462 (14)0.0429 (17)0.0281 (14)0.0054 (12)
C20.0578 (13)0.0453 (12)0.0411 (11)0.0207 (10)0.0114 (9)0.0062 (9)
C30.0425 (11)0.0418 (11)0.0397 (11)0.0168 (9)0.0044 (8)0.0061 (8)
C40.0414 (10)0.0258 (9)0.0380 (10)0.0134 (7)0.0067 (8)0.0040 (7)
C50.0421 (11)0.0473 (12)0.0487 (12)0.0171 (9)0.0033 (9)0.0112 (9)
C60.0567 (14)0.0641 (15)0.0504 (13)0.0217 (12)0.0093 (11)0.0176 (11)
C70.0726 (16)0.0562 (13)0.0368 (11)0.0239 (12)0.0015 (10)0.0133 (10)
C80.0327 (9)0.0336 (9)0.0380 (10)0.0132 (8)0.0061 (7)0.0053 (7)
C90.0402 (10)0.0355 (10)0.0375 (10)0.0166 (8)0.0065 (8)0.0046 (8)
C100.0413 (10)0.0326 (10)0.0347 (9)0.0147 (8)0.0031 (8)0.0095 (7)
C110.0401 (10)0.0333 (10)0.0345 (10)0.0139 (8)0.0032 (8)0.0094 (7)
C120.0542 (13)0.0383 (11)0.0621 (14)0.0207 (10)0.0188 (10)0.0094 (9)
C130.0458 (11)0.0359 (10)0.0376 (10)0.0137 (9)0.0046 (8)0.0096 (8)
C140.0519 (13)0.0426 (12)0.0701 (16)0.0023 (10)0.0125 (11)0.0105 (11)
Geometric parameters (Å, º) top
O1—C21.367 (3)C4—C51.391 (3)
O1—C11.427 (3)C4—C81.525 (2)
O2—C131.340 (2)C5—C61.376 (3)
O2—C141.441 (2)C5—H50.9300
O3—C131.209 (2)C6—C71.382 (3)
O4—C91.235 (2)C6—H60.9300
N1—C91.334 (2)C7—H70.9300
N1—C81.466 (2)C8—C111.521 (2)
N1—H10.8600C8—H80.9800
N2—C91.374 (2)C10—C111.347 (3)
N2—C101.379 (2)C10—C121.493 (3)
N2—H20.8600C11—C131.466 (3)
C1—H1A0.9600C12—H12A0.9600
C1—H1B0.9600C12—H12B0.9600
C1—H1C0.9600C12—H12C0.9600
C2—C71.373 (3)C14—H14A0.9600
C2—C31.393 (3)C14—H14B0.9600
C3—C41.376 (3)C14—H14C0.9600
C3—H30.9300
C2—O1—C1117.3 (2)C6—C7—H7120.4
C13—O2—C14116.35 (17)N1—C8—C11109.47 (14)
C9—N1—C8126.55 (15)N1—C8—C4110.19 (15)
C9—N1—H1116.7C11—C8—C4112.78 (15)
C8—N1—H1116.7N1—C8—H8108.1
C9—N2—C10123.86 (16)C11—C8—H8108.1
C9—N2—H2118.1C4—C8—H8108.1
C10—N2—H2118.1O4—C9—N1123.50 (17)
O1—C1—H1A109.5O4—C9—N2120.59 (17)
O1—C1—H1B109.5N1—C9—N2115.91 (16)
H1A—C1—H1B109.5C11—C10—N2119.78 (16)
O1—C1—H1C109.5C11—C10—C12127.14 (17)
H1A—C1—H1C109.5N2—C10—C12113.08 (16)
H1B—C1—H1C109.5C10—C11—C13121.23 (17)
O1—C2—C7124.9 (2)C10—C11—C8120.57 (16)
O1—C2—C3115.2 (2)C13—C11—C8118.20 (16)
C7—C2—C3119.9 (2)C10—C12—H12A109.5
C4—C3—C2120.69 (19)C10—C12—H12B109.5
C4—C3—H3119.7H12A—C12—H12B109.5
C2—C3—H3119.7C10—C12—H12C109.5
C3—C4—C5119.27 (18)H12A—C12—H12C109.5
C3—C4—C8119.76 (17)H12B—C12—H12C109.5
C5—C4—C8120.96 (17)O3—C13—O2121.45 (18)
C6—C5—C4119.6 (2)O3—C13—C11126.83 (19)
C6—C5—H5120.2O2—C13—C11111.73 (16)
C4—C5—H5120.2O2—C14—H14A109.5
C5—C6—C7121.3 (2)O2—C14—H14B109.5
C5—C6—H6119.3H14A—C14—H14B109.5
C7—C6—H6119.3O2—C14—H14C109.5
C2—C7—C6119.2 (2)H14A—C14—H14C109.5
C2—C7—H7120.4H14B—C14—H14C109.5
C1—O1—C2—C710.6 (3)C8—N1—C9—N25.6 (3)
C1—O1—C2—C3169.5 (2)C10—N2—C9—O4168.65 (18)
O1—C2—C3—C4179.80 (18)C10—N2—C9—N111.0 (3)
C7—C2—C3—C40.3 (3)C9—N2—C10—C1110.5 (3)
C2—C3—C4—C50.4 (3)C9—N2—C10—C12169.51 (18)
C2—C3—C4—C8179.44 (17)N2—C10—C11—C13174.44 (17)
C3—C4—C5—C60.4 (3)C12—C10—C11—C135.6 (3)
C8—C4—C5—C6179.40 (18)N2—C10—C11—C86.1 (3)
C4—C5—C6—C70.2 (3)C12—C10—C11—C8173.91 (18)
O1—C2—C7—C6180.0 (2)N1—C8—C11—C1018.9 (2)
C3—C2—C7—C60.1 (3)C4—C8—C11—C10104.2 (2)
C5—C6—C7—C20.1 (4)N1—C8—C11—C13161.64 (16)
C9—N1—C8—C1119.3 (3)C4—C8—C11—C1375.3 (2)
C9—N1—C8—C4105.3 (2)C14—O2—C13—O30.0 (3)
C3—C4—C8—N1109.25 (19)C14—O2—C13—C11179.94 (17)
C5—C4—C8—N169.8 (2)C10—C11—C13—O30.9 (3)
C3—C4—C8—C11128.10 (18)C8—C11—C13—O3178.5 (2)
C5—C4—C8—C1152.9 (2)C10—C11—C13—O2179.00 (17)
C8—N1—C9—O4174.75 (18)C8—C11—C13—O21.5 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.862.413.146 (2)144
N2—H2···O4ii0.862.002.839 (2)165
Symmetry codes: (i) x, y+1, z; (ii) x, y+2, z+1.
 

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