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The title compound, C14H16N2O2S, was prepared by the reaction of benzaldehyde, ethyl acetoacetate and thio­urea sulfate. There are weak inter­molecular hydrogen-bond inter­actions in the crystal structure, involving the amine and thio­ketone groups as donors and acceptors, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038517/bh2045sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038517/bh2045Isup2.hkl
Contains datablock I

CCDC reference: 602166

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.065
  • wR factor = 0.181
  • Data-to-parameter ratio = 13.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.36 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C6
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 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 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1998); software used to prepare material for publication: WinGX (Farrugia, 1999).

Ethyl 6-methyl-4-phenyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate top
Crystal data top
C14H16N2O2SZ = 2
Mr = 276.35F(000) = 292
Triclinic, P1Dx = 1.357 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.3730 (15) ÅCell parameters from 25 reflections
b = 9.5000 (19) Åθ = 4–14°
c = 11.059 (2) ŵ = 0.24 mm1
α = 69.78 (3)°T = 293 K
β = 89.91 (3)°Block, yellow
γ = 69.89 (3)°0.25 × 0.20 × 0.18 mm
V = 676.5 (2) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.029
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.0°
Graphite monochromatorh = 80
ω scansk = 1110
2591 measured reflectionsl = 1313
2386 independent reflections3 standard reflections every 100 reflections
1603 reflections with I > 2σ(I) intensity decay: <1%
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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0816P)2 + 0.6409P]
where P = (Fo2 + 2Fc2)/3
2386 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.52 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.20336 (15)0.09428 (14)0.54877 (11)0.0443 (4)
O10.8056 (4)0.4283 (4)0.6638 (3)0.0473 (8)
O20.5557 (4)0.5441 (4)0.7550 (3)0.0502 (8)
N10.5210 (4)0.1505 (4)0.5904 (3)0.0353 (8)
H1A0.57340.09620.54290.042*
N20.2451 (5)0.3010 (4)0.6457 (3)0.0350 (8)
H2A0.12780.31520.66300.042*
C10.5400 (8)0.7199 (7)0.8642 (6)0.0698 (16)
H1B0.60260.78290.88620.105*
H1C0.52740.64050.94230.105*
H1D0.41300.78910.81700.105*
C20.6576 (7)0.6391 (6)0.7830 (5)0.0504 (12)
H2B0.66990.71800.70300.060*
H2C0.78710.56970.82900.060*
C30.6437 (6)0.4460 (5)0.6939 (4)0.0338 (9)
C40.5269 (5)0.3567 (5)0.6711 (4)0.0304 (9)
C50.3328 (5)0.3996 (5)0.6688 (4)0.0305 (8)
C60.1911 (6)0.5436 (5)0.6875 (5)0.0473 (12)
H6A0.25920.60690.70290.071*
H6B0.12540.50940.76080.071*
H6C0.09730.60720.61090.071*
C70.3322 (6)0.1845 (5)0.5980 (3)0.0318 (9)
C80.6473 (5)0.1992 (5)0.6575 (4)0.0316 (9)
H8A0.74840.21740.60320.038*
C90.7469 (5)0.0645 (5)0.7871 (4)0.0313 (9)
C100.6885 (6)0.0700 (5)0.9052 (4)0.0386 (10)
H10A0.58530.15960.90620.046*
C110.7795 (7)0.0537 (5)1.0205 (4)0.0460 (11)
H11A0.73850.04721.09860.055*
C120.9304 (7)0.1866 (6)1.0204 (4)0.0480 (11)
H12A0.99230.27061.09840.058*
C130.9907 (6)0.1961 (6)0.9044 (5)0.0504 (12)
H13A1.09250.28710.90420.061*
C140.9011 (6)0.0719 (5)0.7895 (4)0.0414 (10)
H14A0.94400.07880.71180.050*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0350 (6)0.0556 (7)0.0611 (7)0.0210 (5)0.0034 (5)0.0393 (6)
O10.0303 (16)0.064 (2)0.069 (2)0.0247 (15)0.0129 (14)0.0418 (17)
O20.0413 (17)0.063 (2)0.081 (2)0.0324 (16)0.0196 (16)0.0542 (18)
N10.0279 (17)0.049 (2)0.0425 (19)0.0126 (16)0.0000 (14)0.0339 (17)
N20.0271 (17)0.043 (2)0.049 (2)0.0170 (16)0.0092 (15)0.0285 (17)
C10.067 (4)0.085 (4)0.104 (4)0.046 (3)0.028 (3)0.072 (4)
C20.051 (3)0.053 (3)0.074 (3)0.033 (2)0.013 (2)0.040 (3)
C30.033 (2)0.035 (2)0.038 (2)0.0127 (18)0.0014 (17)0.0178 (18)
C40.028 (2)0.036 (2)0.034 (2)0.0127 (18)0.0038 (16)0.0201 (18)
C50.032 (2)0.034 (2)0.032 (2)0.0141 (17)0.0010 (16)0.0174 (17)
C60.028 (2)0.048 (3)0.079 (3)0.011 (2)0.003 (2)0.041 (3)
C70.032 (2)0.040 (2)0.030 (2)0.0154 (18)0.0018 (16)0.0191 (18)
C80.0255 (19)0.041 (2)0.039 (2)0.0155 (18)0.0036 (16)0.0248 (18)
C90.0259 (19)0.039 (2)0.040 (2)0.0170 (18)0.0003 (16)0.0223 (18)
C100.037 (2)0.045 (2)0.042 (2)0.017 (2)0.0046 (19)0.025 (2)
C110.058 (3)0.051 (3)0.038 (2)0.026 (3)0.004 (2)0.021 (2)
C120.045 (3)0.048 (3)0.049 (3)0.019 (2)0.009 (2)0.013 (2)
C130.033 (2)0.045 (3)0.066 (3)0.005 (2)0.006 (2)0.021 (2)
C140.031 (2)0.051 (3)0.052 (3)0.016 (2)0.0064 (19)0.030 (2)
Geometric parameters (Å, º) top
S1—C71.679 (4)C4—C81.514 (5)
O1—C31.210 (5)C5—C61.489 (5)
O2—C31.328 (5)C6—H6A0.9600
O2—C21.461 (5)C6—H6B0.9600
N1—C71.326 (5)C6—H6C0.9600
N1—C81.473 (4)C8—C91.523 (5)
N1—H1A0.8600C8—H8A0.9800
N2—C71.353 (5)C9—C101.387 (5)
N2—C51.393 (4)C9—C141.392 (5)
N2—H2A0.8600C10—C111.372 (6)
C1—C21.471 (6)C10—H10A0.9300
C1—H1B0.9600C11—C121.366 (6)
C1—H1C0.9600C11—H11A0.9300
C1—H1D0.9600C12—C131.379 (6)
C2—H2B0.9700C12—H12A0.9300
C2—H2C0.9700C13—C141.369 (6)
C3—C41.475 (5)C13—H13A0.9300
C4—C51.344 (5)C14—H14A0.9300
C3—O2—C2118.1 (3)C5—C6—H6C109.5
C7—N1—C8124.5 (3)H6A—C6—H6C109.5
C7—N1—H1A117.7H6B—C6—H6C109.5
C8—N1—H1A117.7N1—C7—N2116.0 (3)
C7—N2—C5124.4 (3)N1—C7—S1123.2 (3)
C7—N2—H2A117.8N2—C7—S1120.8 (3)
C5—N2—H2A117.8N1—C8—C4108.9 (3)
C2—C1—H1B109.5N1—C8—C9110.0 (3)
C2—C1—H1C109.5C4—C8—C9113.2 (3)
H1B—C1—H1C109.5N1—C8—H8A108.2
C2—C1—H1D109.5C4—C8—H8A108.2
H1B—C1—H1D109.5C9—C8—H8A108.2
H1C—C1—H1D109.5C10—C9—C14117.6 (4)
O2—C2—C1106.5 (3)C10—C9—C8122.7 (4)
O2—C2—H2B110.4C14—C9—C8119.7 (3)
C1—C2—H2B110.4C11—C10—C9121.5 (4)
O2—C2—H2C110.4C11—C10—H10A119.3
C1—C2—H2C110.4C9—C10—H10A119.3
H2B—C2—H2C108.6C12—C11—C10119.9 (4)
O1—C3—O2123.2 (3)C12—C11—H11A120.0
O1—C3—C4123.6 (4)C10—C11—H11A120.0
O2—C3—C4113.1 (3)C11—C12—C13119.9 (4)
C5—C4—C3125.9 (3)C11—C12—H12A120.0
C5—C4—C8120.2 (3)C13—C12—H12A120.0
C3—C4—C8113.8 (3)C14—C13—C12120.1 (4)
C4—C5—N2118.5 (3)C14—C13—H13A119.9
C4—C5—C6128.4 (3)C12—C13—H13A119.9
N2—C5—C6113.1 (3)C13—C14—C9121.0 (4)
C5—C6—H6A109.5C13—C14—H14A119.5
C5—C6—H6B109.5C9—C14—H14A119.5
H6A—C6—H6B109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···S1i0.862.503.334 (3)165
N2—H2A···O1ii0.862.253.078 (4)162
Symmetry codes: (i) x+1, y, z+1; (ii) x1, y, z.
 

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