organic compounds
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
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038517/bh2045sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038517/bh2045Isup2.hkl |
CCDC reference: 602166
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
C14H16N2O2S | Z = 2 |
Mr = 276.35 | F(000) = 292 |
Triclinic, P1 | Dx = 1.357 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3730 (15) Å | Cell parameters from 25 reflections |
b = 9.5000 (19) Å | θ = 4–14° |
c = 11.059 (2) Å | µ = 0.24 mm−1 |
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 tube | θmax = 25.0°, θmin = 2.0° |
Graphite monochromator | h = −8→0 |
ω scans | k = −11→10 |
2591 measured reflections | l = −13→13 |
2386 independent reflections | 3 standard reflections every 100 reflections |
1603 reflections with I > 2σ(I) | intensity decay: <1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.065 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.181 | H-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 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.52 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
S1 | 0.20336 (15) | 0.09428 (14) | 0.54877 (11) | 0.0443 (4) | |
O1 | 0.8056 (4) | 0.4283 (4) | 0.6638 (3) | 0.0473 (8) | |
O2 | 0.5557 (4) | 0.5441 (4) | 0.7550 (3) | 0.0502 (8) | |
N1 | 0.5210 (4) | 0.1505 (4) | 0.5904 (3) | 0.0353 (8) | |
H1A | 0.5734 | 0.0962 | 0.5429 | 0.042* | |
N2 | 0.2451 (5) | 0.3010 (4) | 0.6457 (3) | 0.0350 (8) | |
H2A | 0.1278 | 0.3152 | 0.6630 | 0.042* | |
C1 | 0.5400 (8) | 0.7199 (7) | 0.8642 (6) | 0.0698 (16) | |
H1B | 0.6026 | 0.7829 | 0.8862 | 0.105* | |
H1C | 0.5274 | 0.6405 | 0.9423 | 0.105* | |
H1D | 0.4130 | 0.7891 | 0.8170 | 0.105* | |
C2 | 0.6576 (7) | 0.6391 (6) | 0.7830 (5) | 0.0504 (12) | |
H2B | 0.6699 | 0.7180 | 0.7030 | 0.060* | |
H2C | 0.7871 | 0.5697 | 0.8290 | 0.060* | |
C3 | 0.6437 (6) | 0.4460 (5) | 0.6939 (4) | 0.0338 (9) | |
C4 | 0.5269 (5) | 0.3567 (5) | 0.6711 (4) | 0.0304 (9) | |
C5 | 0.3328 (5) | 0.3996 (5) | 0.6688 (4) | 0.0305 (8) | |
C6 | 0.1911 (6) | 0.5436 (5) | 0.6875 (5) | 0.0473 (12) | |
H6A | 0.2592 | 0.6069 | 0.7029 | 0.071* | |
H6B | 0.1254 | 0.5094 | 0.7608 | 0.071* | |
H6C | 0.0973 | 0.6072 | 0.6109 | 0.071* | |
C7 | 0.3322 (6) | 0.1845 (5) | 0.5980 (3) | 0.0318 (9) | |
C8 | 0.6473 (5) | 0.1992 (5) | 0.6575 (4) | 0.0316 (9) | |
H8A | 0.7484 | 0.2174 | 0.6032 | 0.038* | |
C9 | 0.7469 (5) | 0.0645 (5) | 0.7871 (4) | 0.0313 (9) | |
C10 | 0.6885 (6) | 0.0700 (5) | 0.9052 (4) | 0.0386 (10) | |
H10A | 0.5853 | 0.1596 | 0.9062 | 0.046* | |
C11 | 0.7795 (7) | −0.0537 (5) | 1.0205 (4) | 0.0460 (11) | |
H11A | 0.7385 | −0.0472 | 1.0986 | 0.055* | |
C12 | 0.9304 (7) | −0.1866 (6) | 1.0204 (4) | 0.0480 (11) | |
H12A | 0.9923 | −0.2706 | 1.0984 | 0.058* | |
C13 | 0.9907 (6) | −0.1961 (6) | 0.9044 (5) | 0.0504 (12) | |
H13A | 1.0925 | −0.2871 | 0.9042 | 0.061* | |
C14 | 0.9011 (6) | −0.0719 (5) | 0.7895 (4) | 0.0414 (10) | |
H14A | 0.9440 | −0.0788 | 0.7118 | 0.050* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0350 (6) | 0.0556 (7) | 0.0611 (7) | −0.0210 (5) | 0.0034 (5) | −0.0393 (6) |
O1 | 0.0303 (16) | 0.064 (2) | 0.069 (2) | −0.0247 (15) | 0.0129 (14) | −0.0418 (17) |
O2 | 0.0413 (17) | 0.063 (2) | 0.081 (2) | −0.0324 (16) | 0.0196 (16) | −0.0542 (18) |
N1 | 0.0279 (17) | 0.049 (2) | 0.0425 (19) | −0.0126 (16) | 0.0000 (14) | −0.0339 (17) |
N2 | 0.0271 (17) | 0.043 (2) | 0.049 (2) | −0.0170 (16) | 0.0092 (15) | −0.0285 (17) |
C1 | 0.067 (4) | 0.085 (4) | 0.104 (4) | −0.046 (3) | 0.028 (3) | −0.072 (4) |
C2 | 0.051 (3) | 0.053 (3) | 0.074 (3) | −0.033 (2) | 0.013 (2) | −0.040 (3) |
C3 | 0.033 (2) | 0.035 (2) | 0.038 (2) | −0.0127 (18) | 0.0014 (17) | −0.0178 (18) |
C4 | 0.028 (2) | 0.036 (2) | 0.034 (2) | −0.0127 (18) | 0.0038 (16) | −0.0201 (18) |
C5 | 0.032 (2) | 0.034 (2) | 0.032 (2) | −0.0141 (17) | 0.0010 (16) | −0.0174 (17) |
C6 | 0.028 (2) | 0.048 (3) | 0.079 (3) | −0.011 (2) | 0.003 (2) | −0.041 (3) |
C7 | 0.032 (2) | 0.040 (2) | 0.030 (2) | −0.0154 (18) | 0.0018 (16) | −0.0191 (18) |
C8 | 0.0255 (19) | 0.041 (2) | 0.039 (2) | −0.0155 (18) | 0.0036 (16) | −0.0248 (18) |
C9 | 0.0259 (19) | 0.039 (2) | 0.040 (2) | −0.0170 (18) | 0.0003 (16) | −0.0223 (18) |
C10 | 0.037 (2) | 0.045 (2) | 0.042 (2) | −0.017 (2) | 0.0046 (19) | −0.025 (2) |
C11 | 0.058 (3) | 0.051 (3) | 0.038 (2) | −0.026 (3) | 0.004 (2) | −0.021 (2) |
C12 | 0.045 (3) | 0.048 (3) | 0.049 (3) | −0.019 (2) | −0.009 (2) | −0.013 (2) |
C13 | 0.033 (2) | 0.045 (3) | 0.066 (3) | −0.005 (2) | −0.006 (2) | −0.021 (2) |
C14 | 0.031 (2) | 0.051 (3) | 0.052 (3) | −0.016 (2) | 0.0064 (19) | −0.030 (2) |
Geometric parameters (Å, º) top
S1—C7 | 1.679 (4) | C4—C8 | 1.514 (5) |
O1—C3 | 1.210 (5) | C5—C6 | 1.489 (5) |
O2—C3 | 1.328 (5) | C6—H6A | 0.9600 |
O2—C2 | 1.461 (5) | C6—H6B | 0.9600 |
N1—C7 | 1.326 (5) | C6—H6C | 0.9600 |
N1—C8 | 1.473 (4) | C8—C9 | 1.523 (5) |
N1—H1A | 0.8600 | C8—H8A | 0.9800 |
N2—C7 | 1.353 (5) | C9—C10 | 1.387 (5) |
N2—C5 | 1.393 (4) | C9—C14 | 1.392 (5) |
N2—H2A | 0.8600 | C10—C11 | 1.372 (6) |
C1—C2 | 1.471 (6) | C10—H10A | 0.9300 |
C1—H1B | 0.9600 | C11—C12 | 1.366 (6) |
C1—H1C | 0.9600 | C11—H11A | 0.9300 |
C1—H1D | 0.9600 | C12—C13 | 1.379 (6) |
C2—H2B | 0.9700 | C12—H12A | 0.9300 |
C2—H2C | 0.9700 | C13—C14 | 1.369 (6) |
C3—C4 | 1.475 (5) | C13—H13A | 0.9300 |
C4—C5 | 1.344 (5) | C14—H14A | 0.9300 |
C3—O2—C2 | 118.1 (3) | C5—C6—H6C | 109.5 |
C7—N1—C8 | 124.5 (3) | H6A—C6—H6C | 109.5 |
C7—N1—H1A | 117.7 | H6B—C6—H6C | 109.5 |
C8—N1—H1A | 117.7 | N1—C7—N2 | 116.0 (3) |
C7—N2—C5 | 124.4 (3) | N1—C7—S1 | 123.2 (3) |
C7—N2—H2A | 117.8 | N2—C7—S1 | 120.8 (3) |
C5—N2—H2A | 117.8 | N1—C8—C4 | 108.9 (3) |
C2—C1—H1B | 109.5 | N1—C8—C9 | 110.0 (3) |
C2—C1—H1C | 109.5 | C4—C8—C9 | 113.2 (3) |
H1B—C1—H1C | 109.5 | N1—C8—H8A | 108.2 |
C2—C1—H1D | 109.5 | C4—C8—H8A | 108.2 |
H1B—C1—H1D | 109.5 | C9—C8—H8A | 108.2 |
H1C—C1—H1D | 109.5 | C10—C9—C14 | 117.6 (4) |
O2—C2—C1 | 106.5 (3) | C10—C9—C8 | 122.7 (4) |
O2—C2—H2B | 110.4 | C14—C9—C8 | 119.7 (3) |
C1—C2—H2B | 110.4 | C11—C10—C9 | 121.5 (4) |
O2—C2—H2C | 110.4 | C11—C10—H10A | 119.3 |
C1—C2—H2C | 110.4 | C9—C10—H10A | 119.3 |
H2B—C2—H2C | 108.6 | C12—C11—C10 | 119.9 (4) |
O1—C3—O2 | 123.2 (3) | C12—C11—H11A | 120.0 |
O1—C3—C4 | 123.6 (4) | C10—C11—H11A | 120.0 |
O2—C3—C4 | 113.1 (3) | C11—C12—C13 | 119.9 (4) |
C5—C4—C3 | 125.9 (3) | C11—C12—H12A | 120.0 |
C5—C4—C8 | 120.2 (3) | C13—C12—H12A | 120.0 |
C3—C4—C8 | 113.8 (3) | C14—C13—C12 | 120.1 (4) |
C4—C5—N2 | 118.5 (3) | C14—C13—H13A | 119.9 |
C4—C5—C6 | 128.4 (3) | C12—C13—H13A | 119.9 |
N2—C5—C6 | 113.1 (3) | C13—C14—C9 | 121.0 (4) |
C5—C6—H6A | 109.5 | C13—C14—H14A | 119.5 |
C5—C6—H6B | 109.5 | C9—C14—H14A | 119.5 |
H6A—C6—H6B | 109.5 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···S1i | 0.86 | 2.50 | 3.334 (3) | 165 |
N2—H2A···O1ii | 0.86 | 2.25 | 3.078 (4) | 162 |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) x−1, y, z. |