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In addition to their wide-ranging applications in the pharmaceutical industry, thio­barbituric acid (TBA) derivatives are also known to possess applications in engineering and materials science. 20 TBA derivatives, with diversity at the N and C-5 positions through acyl­ation, Schiff base formation, Knoevenagel condensation, thio­amide and enamine formation, were studied. The absolute configurations for six derivatives, namely 5-acetyl-1,3-diethyl-2-thioxodi­hydro­pyrimidine-4,6(1H,5H)-dione, C10H14N2O3S, A01, 1,3-diethyl-5-propionyl-2-thioxodi­hydro­pyrimidine-4,6(1H,5H)-dione, C11H16N2O3S, A02, tert-butyl [1-(1,3-diethyl-4,6-dioxo-2-thioxohexa­hydro­pyrimidin-5-yl)-3-methyl-1-oxobutan-2-yl]carbamate, C18H29N3O5S, A06, 1,3-diethyl-4,6-dioxo-2-thioxo-N-(p-tol­yl)hexa­hydro­pyrimidine-5-carbo­thio­amide, C16H19N3O2S2, A13, 5-(1-amino­ethyl­idene)-1,3-diethyl-2-thioxodi­hydro­pyrimidine-4,6(1H,5H)-dione, C10H15N3O2S, A17, and 5-(1-amino­propyl­idene)-1,3-diethyl-2-thioxodi­hydro­pyrimidine-4,6(1H,5H)-dione, C11H17N3O2S, A18, were confirmed by single-crystal X-ray crystallography, which indicates the formation of intra­molecular hydrogen bonding in all six cases and inter­molecular hydrogen bonding for A17. In A13, the presence of two intra­molecular hydrogen bonds was observed. The stabilization of the enol form over the keto form was confirmed by computation. In order to convert the keto form to the enol form, an energy barrier of 55.05 kcal mol−1 needs to be overcome, as confirmed by transition-state calculations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229618015516/fp3065sup1.cif
Contains datablocks A01, A02, A06, A13, A17, A18, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015516/fp3065A01sup2.hkl
Contains datablock A01

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015516/fp3065A02sup3.hkl
Contains datablock A02

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015516/fp3065A06sup4.hkl
Contains datablock A06

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015516/fp3065A13sup5.hkl
Contains datablock A13

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015516/fp3065A17sup6.hkl
Contains datablock A17

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2053229618015516/fp3065A18sup7.hkl
Contains datablock A18

pdf

Portable Document Format (PDF) file https://doi.org/10.1107/S2053229618015516/fp3065sup8.pdf
Spectra for A01-A20: HPLC, NMR, IR and HRMS

CCDC references: 1822987; 1822988; 1822985; 1822984; 1822986; 1822983

Computing details top

For all structures, data collection: APEX2 (Bruker, 2008); cell refinement: SAINT-Plus (Bruker, 2008); data reduction: SAINT-Plus and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

5-Acetyl-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (A01) top
Crystal data top
C10H14N2O3SF(000) = 512
Mr = 242.29Dx = 1.430 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 4.6212 (1) ÅCell parameters from 8036 reflections
b = 12.5742 (4) Åθ = 2.7–28.3°
c = 19.3936 (6) ŵ = 0.28 mm1
β = 92.869 (1)°T = 100 K
V = 1125.51 (6) Å3Rod, colourless
Z = 40.29 × 0.23 × 0.12 mm
Data collection top
Bruker APEXII CCD
diffractometer
2704 independent reflections
Radiation source: sealed tube2309 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
φ and ω scansθmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 56
Tmin = 0.911, Tmax = 0.978k = 1615
14896 measured reflectionsl = 2524
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.041P)2 + 0.5533P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
2704 reflectionsΔρmax = 0.40 e Å3
146 parametersΔρmin = 0.19 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. School of Chemsitry and Physics University of KwaZulu-Natal Private Bag X 54001 Durban 4000

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7202 (3)0.48420 (11)0.60194 (7)0.0266 (3)
H1A0.84780.42380.61340.040*
H1B0.56070.48530.63340.040*
H1C0.64150.47710.55430.040*
C20.8914 (3)0.58714 (10)0.60935 (7)0.0210 (3)
H2A0.97350.59350.65730.025*
H2B1.05450.58530.57810.025*
C30.5442 (3)0.72435 (9)0.64289 (6)0.0160 (2)
C40.2000 (3)0.86382 (11)0.67718 (7)0.0221 (3)
H4A0.12160.80950.70820.027*
H4B0.03440.90210.65430.027*
C50.3853 (4)0.94198 (11)0.71960 (8)0.0302 (3)
H5A0.26760.97580.75410.045*
H5B0.54750.90410.74300.045*
H5C0.46030.99650.68910.045*
C60.3421 (3)0.85049 (10)0.55737 (6)0.0174 (2)
C70.5078 (3)0.80209 (9)0.50516 (6)0.0170 (2)
C80.7076 (3)0.71693 (10)0.52324 (6)0.0183 (2)
C90.4614 (3)0.83582 (10)0.43682 (7)0.0191 (2)
C100.6033 (3)0.79100 (11)0.37626 (7)0.0251 (3)
H10A0.49330.81150.33380.038*
H10B0.60900.71330.37990.038*
H10C0.80130.81860.37510.038*
N10.7069 (2)0.68092 (8)0.59257 (5)0.0165 (2)
N20.3693 (2)0.81041 (8)0.62405 (5)0.0167 (2)
O10.8729 (2)0.67545 (8)0.48428 (5)0.0281 (2)
O20.1740 (2)0.92637 (7)0.54481 (5)0.0236 (2)
O30.2780 (2)0.91243 (8)0.42115 (5)0.0240 (2)
H30.20350.93410.45720.036*
S10.55504 (7)0.67705 (2)0.72282 (2)0.02091 (10)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0310 (7)0.0206 (6)0.0278 (7)0.0059 (5)0.0021 (5)0.0034 (5)
C20.0181 (6)0.0226 (6)0.0219 (6)0.0061 (5)0.0021 (5)0.0006 (5)
C30.0139 (5)0.0162 (5)0.0179 (6)0.0027 (4)0.0008 (4)0.0016 (4)
C40.0217 (6)0.0239 (6)0.0213 (6)0.0049 (5)0.0070 (5)0.0015 (5)
C50.0407 (9)0.0231 (7)0.0272 (7)0.0010 (6)0.0064 (6)0.0074 (5)
C60.0152 (6)0.0182 (5)0.0188 (6)0.0015 (4)0.0010 (4)0.0007 (4)
C70.0153 (6)0.0188 (6)0.0167 (6)0.0015 (4)0.0000 (4)0.0001 (4)
C80.0165 (6)0.0204 (6)0.0178 (6)0.0007 (4)0.0004 (4)0.0002 (5)
C90.0162 (6)0.0214 (6)0.0194 (6)0.0033 (4)0.0008 (4)0.0009 (5)
C100.0277 (7)0.0304 (7)0.0170 (6)0.0007 (5)0.0007 (5)0.0005 (5)
N10.0150 (5)0.0175 (5)0.0170 (5)0.0019 (4)0.0004 (4)0.0003 (4)
N20.0162 (5)0.0175 (5)0.0164 (5)0.0014 (4)0.0017 (4)0.0009 (4)
O10.0285 (5)0.0351 (6)0.0214 (5)0.0119 (4)0.0075 (4)0.0014 (4)
O20.0239 (5)0.0232 (5)0.0235 (5)0.0076 (4)0.0008 (4)0.0018 (4)
O30.0247 (5)0.0271 (5)0.0200 (5)0.0036 (4)0.0008 (4)0.0028 (4)
S10.02501 (18)0.02170 (17)0.01597 (16)0.00059 (11)0.00046 (11)0.00196 (11)
Geometric parameters (Å, º) top
C1—C21.5202 (19)C5—H5B0.9800
C1—H1A0.9800C5—H5C0.9800
C1—H1B0.9800C6—O21.2469 (15)
C1—H1C0.9800C6—N21.3877 (16)
C2—N11.4818 (15)C6—C71.4350 (17)
C2—H2A0.9900C7—C91.3979 (17)
C2—H2B0.9900C7—C81.4457 (17)
C3—N11.3746 (16)C8—O11.2184 (16)
C3—N21.3887 (15)C8—N11.4188 (16)
C3—S11.6588 (12)C9—O31.3089 (15)
C4—N21.4849 (15)C9—C101.4847 (18)
C4—C51.518 (2)C10—H10A0.9800
C4—H4A0.9900C10—H10B0.9800
C4—H4B0.9900C10—H10C0.9800
C5—H5A0.9800O3—H30.8400
C2—C1—H1A109.5H5B—C5—H5C109.5
C2—C1—H1B109.5O2—C6—N2119.10 (11)
H1A—C1—H1B109.5O2—C6—C7122.41 (11)
C2—C1—H1C109.5N2—C6—C7118.49 (11)
H1A—C1—H1C109.5C9—C7—C6118.59 (11)
H1B—C1—H1C109.5C9—C7—C8121.36 (11)
N1—C2—C1111.45 (10)C6—C7—C8119.99 (11)
N1—C2—H2A109.3O1—C8—N1118.83 (11)
C1—C2—H2A109.3O1—C8—C7125.41 (12)
N1—C2—H2B109.3N1—C8—C7115.75 (11)
C1—C2—H2B109.3O3—C9—C7120.68 (12)
H2A—C2—H2B108.0O3—C9—C10113.72 (11)
N1—C3—N2117.05 (10)C7—C9—C10125.59 (12)
N1—C3—S1121.94 (9)C9—C10—H10A109.5
N2—C3—S1121.01 (9)C9—C10—H10B109.5
N2—C4—C5111.49 (11)H10A—C10—H10B109.5
N2—C4—H4A109.3C9—C10—H10C109.5
C5—C4—H4A109.3H10A—C10—H10C109.5
N2—C4—H4B109.3H10B—C10—H10C109.5
C5—C4—H4B109.3C3—N1—C8124.98 (10)
H4A—C4—H4B108.0C3—N1—C2119.30 (10)
C4—C5—H5A109.5C8—N1—C2115.70 (10)
C4—C5—H5B109.5C6—N2—C3123.53 (10)
H5A—C5—H5B109.5C6—N2—C4117.14 (10)
C4—C5—H5C109.5C3—N2—C4119.33 (10)
H5A—C5—H5C109.5C9—O3—H3109.5
O2—C6—C7—C95.16 (18)O1—C8—N1—C3176.16 (12)
N2—C6—C7—C9174.28 (11)C7—C8—N1—C33.50 (17)
O2—C6—C7—C8177.67 (11)O1—C8—N1—C25.83 (17)
N2—C6—C7—C82.89 (17)C7—C8—N1—C2174.51 (10)
C9—C7—C8—O18.3 (2)C1—C2—N1—C384.75 (14)
C6—C7—C8—O1174.57 (12)C1—C2—N1—C893.38 (13)
C9—C7—C8—N1172.03 (11)O2—C6—N2—C3178.14 (11)
C6—C7—C8—N15.06 (17)C7—C6—N2—C31.32 (17)
C6—C7—C9—O32.29 (18)O2—C6—N2—C41.88 (17)
C8—C7—C9—O3179.42 (11)C7—C6—N2—C4178.66 (11)
C6—C7—C9—C10177.00 (12)N1—C3—N2—C62.99 (17)
C8—C7—C9—C100.13 (19)S1—C3—N2—C6177.18 (9)
N2—C3—N1—C80.42 (17)N1—C3—N2—C4176.99 (10)
S1—C3—N1—C8179.74 (9)S1—C3—N2—C42.84 (15)
N2—C3—N1—C2178.36 (10)C5—C4—N2—C698.68 (13)
S1—C3—N1—C21.80 (15)C5—C4—N2—C381.30 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5B···S10.982.883.4223 (15)116
C10—H10A···S1i0.982.883.8316 (14)163
O3—H3···O20.841.712.4756 (13)150
O3—H3···O2ii0.842.473.0073 (13)122
Symmetry codes: (i) x1/2, y+3/2, z1/2; (ii) x, y+2, z+1.
1,3-Diethyl-5-propionyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (A02) top
Crystal data top
C11H16N2O3SF(000) = 272
Mr = 256.32Dx = 1.409 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 4.9140 (1) ÅCell parameters from 7194 reflections
b = 12.9450 (3) Åθ = 2.7–27.5°
c = 9.7630 (3) ŵ = 0.27 mm1
β = 103.474 (1)°T = 100 K
V = 603.95 (3) Å3Block, colourless
Z = 20.19 × 0.14 × 0.07 mm
Data collection top
Bruker APEXII CCD
diffractometer
8623 independent reflections
Radiation source: sealed tube8469 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
φ and ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 66
Tmin = 0.940, Tmax = 0.991k = 1616
8623 measured reflectionsl = 1212
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.027 w = 1/[σ2(Fo2) + (0.0441P)2 + 0.0526P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.070(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.21 e Å3
8623 reflectionsΔρmin = 0.26 e Å3
158 parametersAbsolute structure: Flack x determined using 1252 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.034 (16)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3177 (3)0.72567 (12)0.49804 (17)0.0214 (4)
O20.1016 (3)0.37732 (11)0.38393 (16)0.0186 (3)
C50.1988 (4)0.54922 (16)0.4577 (2)0.0146 (4)
N20.4821 (4)0.64360 (14)0.32802 (19)0.0155 (4)
C10.1348 (5)0.58442 (19)0.7760 (3)0.0281 (6)
H1A0.0307960.5266900.8284700.042*
H1B0.3249360.5617940.7309330.042*
H1C0.1438500.6414430.8408240.042*
C20.0123 (4)0.62058 (18)0.6641 (2)0.0191 (5)
H2A0.0939810.6791080.6122540.023*
H2B0.2005160.6464460.7111330.023*
C30.0435 (4)0.53884 (15)0.5607 (2)0.0159 (4)
C40.2242 (4)0.46125 (17)0.3735 (2)0.0155 (4)
N10.3909 (3)0.46756 (14)0.27790 (19)0.0157 (4)
C60.4312 (4)0.37043 (16)0.2038 (2)0.0176 (5)
H6A0.4343220.3112610.2684160.021*
H6B0.6143150.3729120.1780060.021*
C70.2017 (4)0.35365 (19)0.0718 (2)0.0234 (5)
H7A0.0208230.3479830.0973780.035*
H7B0.2387720.2899220.0251530.035*
H7C0.1971130.4122240.0077450.035*
C80.5062 (4)0.55963 (19)0.2455 (2)0.0160 (4)
C90.3308 (4)0.64530 (17)0.4348 (2)0.0158 (4)
O30.0832 (3)0.45221 (11)0.57302 (17)0.0198 (3)
H30.0534350.4098230.5130110.030*
C110.6030 (4)0.74399 (18)0.2997 (2)0.0198 (5)
H11A0.7718940.7315670.2631240.024*
H11B0.6605590.7832410.3888040.024*
C120.3955 (5)0.80712 (19)0.1941 (3)0.0261 (5)
H12A0.3341320.7675870.1067810.039*
H12B0.4843580.8714490.1743720.039*
H12C0.2334200.8233100.2327390.039*
S10.66844 (10)0.56606 (5)0.11383 (6)0.02182 (15)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0278 (8)0.0164 (8)0.0221 (8)0.0033 (6)0.0104 (7)0.0031 (6)
O20.0214 (7)0.0139 (7)0.0221 (8)0.0018 (6)0.0085 (6)0.0006 (6)
C50.0156 (8)0.0131 (12)0.0152 (9)0.0000 (8)0.0036 (7)0.0004 (8)
N20.0164 (8)0.0136 (9)0.0172 (10)0.0022 (7)0.0053 (7)0.0004 (7)
C10.0436 (13)0.0212 (14)0.0252 (12)0.0035 (10)0.0193 (11)0.0023 (9)
C20.0241 (10)0.0177 (11)0.0176 (11)0.0017 (9)0.0090 (9)0.0006 (8)
C30.0150 (9)0.0154 (11)0.0166 (10)0.0025 (8)0.0022 (8)0.0027 (8)
C40.0133 (9)0.0162 (10)0.0164 (10)0.0025 (8)0.0020 (8)0.0035 (8)
N10.0180 (9)0.0138 (9)0.0161 (9)0.0020 (7)0.0056 (7)0.0005 (7)
C60.0198 (10)0.0127 (11)0.0217 (11)0.0033 (8)0.0080 (9)0.0015 (8)
C70.0252 (11)0.0235 (13)0.0217 (12)0.0033 (9)0.0056 (9)0.0043 (10)
C80.0135 (8)0.0163 (10)0.0178 (10)0.0018 (9)0.0027 (8)0.0007 (9)
C90.0150 (9)0.0166 (11)0.0152 (11)0.0012 (8)0.0021 (8)0.0015 (9)
O30.0249 (8)0.0143 (8)0.0234 (9)0.0015 (6)0.0122 (7)0.0008 (6)
C110.0228 (10)0.0165 (11)0.0218 (12)0.0057 (8)0.0089 (9)0.0003 (9)
C120.0334 (12)0.0172 (12)0.0320 (14)0.0044 (10)0.0163 (11)0.0074 (10)
S10.0268 (3)0.0199 (3)0.0233 (3)0.0010 (2)0.0151 (2)0.0016 (2)
Geometric parameters (Å, º) top
O1—C91.219 (3)N1—C81.388 (3)
O2—C41.258 (3)N1—C61.487 (3)
C5—C31.403 (3)C6—C71.517 (3)
C5—C41.427 (3)C6—H6A0.9900
C5—C91.444 (3)C6—H6B0.9900
N2—C81.375 (3)C7—H7A0.9800
N2—C91.415 (3)C7—H7B0.9800
N2—C111.481 (3)C7—H7C0.9800
C1—C21.518 (3)C8—S11.665 (2)
C1—H1A0.9800O3—H30.8400
C1—H1B0.9800C11—C121.510 (3)
C1—H1C0.9800C11—H11A0.9900
C2—C31.495 (3)C11—H11B0.9900
C2—H2A0.9900C12—H12A0.9800
C2—H2B0.9900C12—H12B0.9800
C3—O31.302 (2)C12—H12C0.9800
C4—N11.380 (3)
C3—C5—C4118.13 (18)C7—C6—H6A109.2
C3—C5—C9122.15 (18)N1—C6—H6B109.2
C4—C5—C9119.72 (18)C7—C6—H6B109.2
C8—N2—C9125.18 (18)H6A—C6—H6B107.9
C8—N2—C11119.42 (17)C6—C7—H7A109.5
C9—N2—C11115.24 (18)C6—C7—H7B109.5
C2—C1—H1A109.5H7A—C7—H7B109.5
C2—C1—H1B109.5C6—C7—H7C109.5
H1A—C1—H1B109.5H7A—C7—H7C109.5
C2—C1—H1C109.5H7B—C7—H7C109.5
H1A—C1—H1C109.5N2—C8—N1116.74 (17)
H1B—C1—H1C109.5N2—C8—S1122.36 (17)
C3—C2—C1114.14 (19)N1—C8—S1120.90 (17)
C3—C2—H2A108.7O1—C9—N2119.02 (19)
C1—C2—H2A108.7O1—C9—C5125.34 (19)
C3—C2—H2B108.7N2—C9—C5115.63 (18)
C1—C2—H2B108.7C3—O3—H3109.5
H2A—C2—H2B107.6N2—C11—C12111.45 (17)
O3—C3—C5120.04 (19)N2—C11—H11A109.3
O3—C3—C2114.87 (18)C12—C11—H11A109.3
C5—C3—C2125.08 (18)N2—C11—H11B109.3
O2—C4—N1118.5 (2)C12—C11—H11B109.3
O2—C4—C5122.33 (19)H11A—C11—H11B108.0
N1—C4—C5119.19 (18)C11—C12—H12A109.5
C4—N1—C8122.91 (18)C11—C12—H12B109.5
C4—N1—C6116.51 (17)H12A—C12—H12B109.5
C8—N1—C6120.51 (17)C11—C12—H12C109.5
N1—C6—C7112.16 (17)H12A—C12—H12C109.5
N1—C6—H6A109.2H12B—C12—H12C109.5
C4—C5—C3—O33.1 (3)C11—N2—C8—N1179.47 (16)
C9—C5—C3—O3176.66 (18)C9—N2—C8—S1175.37 (14)
C4—C5—C3—C2175.57 (18)C11—N2—C8—S10.2 (3)
C9—C5—C3—C24.6 (3)C4—N1—C8—N29.3 (3)
C1—C2—C3—O36.4 (3)C6—N1—C8—N2173.90 (16)
C1—C2—C3—C5172.34 (19)C4—N1—C8—S1171.45 (15)
C3—C5—C4—O23.6 (3)C6—N1—C8—S15.3 (3)
C9—C5—C4—O2176.22 (18)C8—N2—C9—O1177.70 (19)
C3—C5—C4—N1175.80 (18)C11—N2—C9—O12.4 (3)
C9—C5—C4—N14.4 (3)C8—N2—C9—C51.3 (3)
O2—C4—N1—C8171.61 (18)C11—N2—C9—C5176.63 (16)
C5—C4—N1—C89.0 (3)C3—C5—C9—O11.6 (3)
O2—C4—N1—C65.3 (3)C4—C5—C9—O1178.24 (19)
C5—C4—N1—C6174.09 (16)C3—C5—C9—N2179.51 (18)
C4—N1—C6—C787.0 (2)C4—C5—C9—N20.7 (3)
C8—N1—C6—C790.0 (2)C8—N2—C11—C1288.9 (2)
C9—N2—C8—N15.4 (3)C9—N2—C11—C1286.7 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···O2i0.992.573.385 (3)140
C6—H6A···O1ii0.992.573.440 (3)146
C11—H11B···O2iii0.992.563.541 (3)170
O3—H3···O20.841.672.440 (2)151
Symmetry codes: (i) x, y+1/2, z+1; (ii) x+1, y1/2, z+1; (iii) x+1, y+1/2, z+1.
tert-Butyl [1-(1,3-diethyl-4,6-dioxo-2-thioxohexahydropyrimidin-5-yl)-3-methyl-1-oxobutan-2-yl)carbamate (A06) top
Crystal data top
C18H29N3O5SDx = 1.354 Mg m3
Mr = 399.50Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 9709 reflections
a = 8.3816 (12) Åθ = 2.3–27.6°
b = 9.6258 (14) ŵ = 0.20 mm1
c = 24.297 (3) ÅT = 100 K
V = 1960.3 (5) Å3Block, colourless
Z = 40.33 × 0.25 × 0.21 mm
F(000) = 856
Data collection top
Bruker APEXII CCD
diffractometer
15360 independent reflections
Radiation source: sealed tube14556 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
φ and ω scansθmax = 27.7°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 108
Tmin = 0.925, Tmax = 0.968k = 1212
15360 measured reflectionsl = 3128
Refinement top
Refinement on F2Hydrogen site location: mixed
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.028 w = 1/[σ2(Fo2) + (0.0272P)2 + 0.5031P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.070(Δ/σ)max = 0.001
S = 1.04Δρmax = 0.47 e Å3
15360 reflectionsΔρmin = 0.30 e Å3
264 parametersAbsolute structure: Flack x determined using 1707 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
5 restraintsAbsolute structure parameter: 0.001 (2)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.2383 (3)0.8543 (3)0.93914 (10)0.0272 (6)
H1A0.1761110.7808710.9212120.041*
H1B0.1656610.9214010.9562210.041*
H1C0.3069060.8131870.9674560.041*
C20.3395 (3)0.9267 (2)0.89713 (9)0.0179 (5)
H2A0.2695590.9742700.8702590.021*
H2B0.4052630.9981940.9156420.021*
C80.3789 (3)0.7723 (2)0.81999 (9)0.0147 (5)
C90.4471 (3)0.6340 (2)0.73724 (9)0.0157 (5)
C100.2971 (2)0.6640 (2)0.70544 (9)0.0154 (5)
H100.2444440.7488730.7207660.018*
C150.6228 (3)0.8459 (2)0.56077 (10)0.0204 (5)
C140.4478 (3)0.7825 (2)0.63569 (9)0.0170 (5)
C170.6270 (3)0.7970 (3)0.50255 (10)0.0302 (6)
H17A0.5284640.8247400.4838540.045*
H17B0.6366860.6955250.5018530.045*
H17C0.7187450.8384760.4836970.045*
C30.5935 (3)0.8077 (2)0.88664 (9)0.0172 (5)
C60.6383 (3)0.6611 (2)0.80864 (9)0.0170 (5)
N20.6884 (2)0.72189 (19)0.85597 (8)0.0165 (4)
C40.8554 (3)0.6961 (3)0.87195 (10)0.0249 (6)
H4A0.8945120.7748900.8943990.030*
H4B0.9222930.6904590.8384280.030*
C50.8721 (3)0.5651 (3)0.90395 (12)0.0366 (7)
H5A0.8396800.4862130.8810320.055*
H5B0.8041310.5694450.9367150.055*
H5C0.9836220.5532830.9151870.055*
C110.1811 (3)0.5412 (2)0.70810 (10)0.0190 (5)
H110.2289930.4638150.6861880.023*
C120.1553 (3)0.4880 (3)0.76531 (10)0.0252 (6)
H12A0.0799670.4102480.7644020.038*
H12B0.1119860.5626020.7883420.038*
H12C0.2572400.4564670.7806290.038*
C130.0255 (3)0.5789 (3)0.68128 (11)0.0294 (6)
H13A0.0450630.6079530.6432220.044*
H13B0.0244730.6552390.7016330.044*
H13C0.0455040.4980080.6814960.044*
C180.5949 (3)0.9999 (2)0.56391 (12)0.0336 (7)
H18A0.6767421.0483850.5424460.050*
H18B0.6004271.0301110.6023860.050*
H18C0.4892151.0217700.5489490.050*
C160.7711 (3)0.8032 (3)0.59051 (11)0.0279 (6)
H16A0.7822230.7019340.5889170.042*
H16B0.7644160.8329030.6290210.042*
H16C0.8639320.8467810.5730800.042*
N10.4442 (2)0.83019 (18)0.86787 (7)0.0140 (4)
C70.4840 (3)0.6877 (2)0.78880 (9)0.0139 (5)
N30.3372 (2)0.6871 (2)0.64868 (8)0.0170 (4)
O10.24103 (17)0.79625 (16)0.80922 (6)0.0184 (4)
O20.73574 (18)0.58447 (17)0.78407 (7)0.0210 (4)
O30.54486 (19)0.55537 (17)0.71284 (7)0.0203 (4)
O40.50057 (18)0.86552 (17)0.66745 (6)0.0223 (4)
O50.48618 (18)0.77041 (17)0.58289 (6)0.0192 (4)
S10.66106 (8)0.88046 (6)0.94304 (3)0.02442 (16)
H30.327 (3)0.624 (2)0.6266 (9)0.027 (7)*
H20.695 (3)0.563 (5)0.7528 (9)0.03 (2)*0.50 (7)
H3A0.627 (3)0.549 (5)0.7338 (10)0.03 (2)*0.50 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0309 (14)0.0277 (13)0.0229 (13)0.0047 (12)0.0080 (12)0.0008 (12)
C20.0224 (12)0.0172 (11)0.0141 (12)0.0049 (11)0.0003 (10)0.0028 (9)
C80.0179 (12)0.0122 (10)0.0141 (11)0.0019 (10)0.0012 (10)0.0018 (9)
C90.0157 (12)0.0134 (11)0.0179 (12)0.0023 (11)0.0042 (9)0.0013 (10)
C100.0150 (12)0.0169 (12)0.0142 (11)0.0007 (9)0.0004 (9)0.0017 (10)
C150.0230 (12)0.0185 (11)0.0196 (12)0.0056 (10)0.0075 (11)0.0014 (10)
C140.0179 (12)0.0176 (11)0.0155 (12)0.0025 (11)0.0008 (10)0.0002 (10)
C170.0366 (16)0.0328 (15)0.0211 (13)0.0102 (13)0.0074 (12)0.0023 (12)
C30.0217 (13)0.0130 (11)0.0168 (12)0.0013 (10)0.0012 (10)0.0031 (10)
C60.0191 (12)0.0148 (11)0.0172 (12)0.0009 (10)0.0021 (10)0.0014 (9)
N20.0139 (10)0.0171 (9)0.0186 (10)0.0012 (8)0.0026 (8)0.0002 (9)
C40.0152 (12)0.0308 (14)0.0286 (14)0.0040 (12)0.0070 (11)0.0051 (12)
C50.0322 (15)0.0345 (15)0.0430 (18)0.0137 (13)0.0141 (14)0.0005 (14)
C110.0184 (12)0.0192 (12)0.0192 (13)0.0032 (10)0.0012 (10)0.0004 (10)
C120.0254 (13)0.0251 (13)0.0251 (14)0.0051 (12)0.0032 (11)0.0050 (11)
C130.0205 (13)0.0364 (15)0.0314 (15)0.0089 (12)0.0048 (11)0.0080 (13)
C180.0482 (17)0.0222 (13)0.0304 (16)0.0015 (13)0.0112 (14)0.0046 (12)
C160.0215 (13)0.0319 (15)0.0303 (15)0.0054 (12)0.0054 (11)0.0049 (13)
N10.0149 (10)0.0143 (9)0.0128 (9)0.0016 (8)0.0001 (8)0.0001 (8)
C70.0128 (11)0.0143 (11)0.0145 (11)0.0008 (9)0.0008 (9)0.0017 (9)
N30.0203 (10)0.0178 (10)0.0129 (10)0.0044 (9)0.0010 (9)0.0026 (9)
O10.0139 (8)0.0234 (9)0.0180 (9)0.0036 (7)0.0011 (7)0.0028 (7)
O20.0167 (8)0.0258 (10)0.0205 (10)0.0058 (7)0.0008 (8)0.0050 (8)
O30.0172 (9)0.0247 (9)0.0190 (9)0.0048 (8)0.0003 (8)0.0065 (7)
O40.0264 (9)0.0207 (8)0.0199 (9)0.0064 (8)0.0019 (7)0.0045 (8)
O50.0211 (9)0.0230 (9)0.0134 (8)0.0070 (7)0.0028 (7)0.0002 (7)
S10.0295 (3)0.0236 (3)0.0201 (3)0.0030 (3)0.0098 (3)0.0048 (3)
Geometric parameters (Å, º) top
C1—C21.499 (3)C6—O21.252 (3)
C1—H1A0.9800C6—N21.357 (3)
C1—H1B0.9800C6—C71.404 (3)
C1—H1C0.9800N2—C41.474 (3)
C2—N11.462 (3)C4—C51.488 (3)
C2—H2A0.9900C4—H4A0.9900
C2—H2B0.9900C4—H4B0.9900
C8—O11.207 (3)C5—H5A0.9800
C8—N11.401 (3)C5—H5B0.9800
C8—C71.419 (3)C5—H5C0.9800
C9—O31.263 (3)C11—C121.497 (3)
C9—C71.390 (3)C11—C131.502 (3)
C9—C101.504 (3)C11—H111.0000
C10—N31.437 (3)C12—H12A0.9800
C10—C111.532 (3)C12—H12B0.9800
C10—H101.0000C12—H12C0.9800
C15—O51.459 (3)C13—H13A0.9800
C15—C171.491 (3)C13—H13B0.9800
C15—C161.496 (3)C13—H13C0.9800
C15—C181.503 (3)C18—H18A0.9800
C14—O41.196 (3)C18—H18B0.9800
C14—O51.328 (3)C18—H18C0.9800
C14—N31.343 (3)C16—H16A0.9800
C17—H17A0.9800C16—H16B0.9800
C17—H17B0.9800C16—H16C0.9800
C17—H17C0.9800N3—H30.816 (18)
C3—N11.349 (3)O2—H20.860 (3)
C3—N21.368 (3)O3—H3A0.860 (3)
C3—S11.640 (2)
C2—C1—H1A109.5N2—C4—H4B109.3
C2—C1—H1B109.5C5—C4—H4B109.3
H1A—C1—H1B109.5H4A—C4—H4B107.9
C2—C1—H1C109.5C4—C5—H5A109.5
H1A—C1—H1C109.5C4—C5—H5B109.5
H1B—C1—H1C109.5H5A—C5—H5B109.5
N1—C2—C1112.05 (19)C4—C5—H5C109.5
N1—C2—H2A109.2H5A—C5—H5C109.5
C1—C2—H2A109.2H5B—C5—H5C109.5
N1—C2—H2B109.2C12—C11—C13111.1 (2)
C1—C2—H2B109.2C12—C11—C10113.2 (2)
H2A—C2—H2B107.9C13—C11—C10110.26 (19)
O1—C8—N1118.5 (2)C12—C11—H11107.3
O1—C8—C7126.0 (2)C13—C11—H11107.3
N1—C8—C7115.43 (19)C10—C11—H11107.3
O3—C9—C7120.1 (2)C11—C12—H12A109.5
O3—C9—C10114.61 (19)C11—C12—H12B109.5
C7—C9—C10125.3 (2)H12A—C12—H12B109.5
N3—C10—C9109.09 (18)C11—C12—H12C109.5
N3—C10—C11107.94 (19)H12A—C12—H12C109.5
C9—C10—C11111.15 (18)H12B—C12—H12C109.5
N3—C10—H10109.5C11—C13—H13A109.5
C9—C10—H10109.5C11—C13—H13B109.5
C11—C10—H10109.5H13A—C13—H13B109.5
O5—C15—C17102.17 (18)C11—C13—H13C109.5
O5—C15—C16109.71 (18)H13A—C13—H13C109.5
C17—C15—C16110.6 (2)H13B—C13—H13C109.5
O5—C15—C18110.53 (19)C15—C18—H18A109.5
C17—C15—C18111.3 (2)C15—C18—H18B109.5
C16—C15—C18112.1 (2)H18A—C18—H18B109.5
O4—C14—O5126.3 (2)C15—C18—H18C109.5
O4—C14—N3124.1 (2)H18A—C18—H18C109.5
O5—C14—N3109.6 (2)H18B—C18—H18C109.5
C15—C17—H17A109.5C15—C16—H16A109.5
C15—C17—H17B109.5C15—C16—H16B109.5
H17A—C17—H17B109.5H16A—C16—H16B109.5
C15—C17—H17C109.5C15—C16—H16C109.5
H17A—C17—H17C109.5H16A—C16—H16C109.5
H17B—C17—H17C109.5H16B—C16—H16C109.5
N1—C3—N2116.87 (19)C3—N1—C8125.37 (18)
N1—C3—S1122.31 (17)C3—N1—C2119.59 (19)
N2—C3—S1120.81 (17)C8—N1—C2114.98 (17)
O2—C6—N2117.1 (2)C9—C7—C6116.5 (2)
O2—C6—C7123.0 (2)C9—C7—C8123.8 (2)
N2—C6—C7119.8 (2)C6—C7—C8119.6 (2)
C6—N2—C3122.84 (19)C14—N3—C10119.53 (19)
C6—N2—C4116.39 (19)C14—N3—H3115.5 (18)
C3—N2—C4120.72 (19)C10—N3—H3119.3 (18)
N2—C4—C5111.7 (2)C6—O2—H2107.6 (4)
N2—C4—H4A109.3C9—O3—H3A106.6 (4)
C5—C4—H4A109.3C14—O5—C15120.17 (18)
O3—C9—C10—N341.3 (3)C7—C8—N1—C2174.93 (18)
C7—C9—C10—N3137.3 (2)C1—C2—N1—C392.5 (2)
O3—C9—C10—C1177.6 (2)C1—C2—N1—C890.1 (2)
C7—C9—C10—C11103.8 (3)O3—C9—C7—C66.1 (3)
O2—C6—N2—C3180.0 (2)C10—C9—C7—C6172.4 (2)
C7—C6—N2—C31.2 (3)O3—C9—C7—C8177.47 (19)
O2—C6—N2—C42.8 (3)C10—C9—C7—C84.0 (3)
C7—C6—N2—C4176.0 (2)O2—C6—C7—C95.4 (3)
N1—C3—N2—C60.2 (3)N2—C6—C7—C9173.3 (2)
S1—C3—N2—C6179.03 (17)O2—C6—C7—C8178.0 (2)
N1—C3—N2—C4177.34 (19)N2—C6—C7—C83.3 (3)
S1—C3—N2—C41.9 (3)O1—C8—C7—C98.4 (4)
C6—N2—C4—C586.0 (3)N1—C8—C7—C9172.6 (2)
C3—N2—C4—C596.7 (3)O1—C8—C7—C6175.3 (2)
N3—C10—C11—C12168.4 (2)N1—C8—C7—C63.7 (3)
C9—C10—C11—C1248.8 (3)O4—C14—N3—C1011.4 (3)
N3—C10—C11—C1366.4 (2)O5—C14—N3—C10169.31 (19)
C9—C10—C11—C13174.0 (2)C9—C10—N3—C1453.7 (3)
N2—C3—N1—C80.4 (3)C11—C10—N3—C14174.61 (19)
S1—C3—N1—C8179.63 (17)O4—C14—O5—C1511.1 (3)
N2—C3—N1—C2176.76 (18)N3—C14—O5—C15169.58 (18)
S1—C3—N1—C22.5 (3)C17—C15—O5—C14177.0 (2)
O1—C8—N1—C3176.7 (2)C16—C15—O5—C1459.7 (3)
C7—C8—N1—C32.3 (3)C18—C15—O5—C1464.4 (3)
O1—C8—N1—C26.0 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O11.002.202.863 (3)123
C11—H11···N2i1.002.643.615 (3)166
C18—H18A···S1ii0.982.863.760 (3)154
C18—H18B···O40.982.392.937 (3)115
C16—H16B···O40.982.423.000 (3)117
N3—H3···S1i0.82 (2)2.89 (2)3.698 (2)170 (2)
O2—H2···O30.86 (1)1.59 (1)2.374 (2)150 (1)
O3—H3A···O20.86 (1)1.56 (1)2.374 (2)156 (1)
Symmetry codes: (i) x+1, y1/2, z+3/2; (ii) x+3/2, y+2, z1/2.
1,3-Diethyl-4,6-dioxo-2-thioxo-<i.N-(p-tolyl)hexahydropyrimidine-5-carbothioamide (A13) top
Crystal data top
C16H19N3O2S2F(000) = 736
Mr = 349.46Dx = 1.467 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 4.8156 (2) ÅCell parameters from 9954 reflections
b = 21.7395 (7) Åθ = 2.3–28.6°
c = 15.1912 (5) ŵ = 0.35 mm1
β = 95.656 (1)°T = 100 K
V = 1582.61 (10) Å3Rod, yellow
Z = 40.19 × 0.12 × 0.11 mm
Data collection top
Bruker APEXII CCD
diffractometer
4036 independent reflections
Radiation source: sealed tube3430 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 28.7°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 66
Tmin = 0.925, Tmax = 0.976k = 2829
25387 measured reflectionsl = 1620
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.031H-atom parameters constrained
wR(F2) = 0.078 w = 1/[σ2(Fo2) + (0.0319P)2 + 0.9919P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.003
4036 reflectionsΔρmax = 0.38 e Å3
212 parametersΔρmin = 0.25 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6364 (3)0.05024 (7)1.11011 (9)0.0200 (3)
H1A0.4446170.0593131.1223810.030*
H1B0.7381100.0316611.1625360.030*
H1C0.6335370.0215471.0602730.030*
C20.7801 (3)0.10933 (6)1.08713 (9)0.0165 (3)
H2B0.8022750.1362481.1399250.020*
H2C0.9685960.0995991.0702630.020*
C30.4240 (3)0.18473 (6)1.03472 (8)0.0130 (2)
C40.2647 (3)0.21854 (6)0.96914 (8)0.0122 (2)
C50.0575 (3)0.26444 (6)0.99080 (8)0.0124 (2)
C60.2913 (3)0.33867 (6)0.91476 (8)0.0132 (3)
C70.4266 (3)0.34618 (6)0.82949 (9)0.0153 (3)
H70.3790580.3203320.7828410.018*
C80.6294 (3)0.39103 (6)0.81270 (9)0.0166 (3)
H80.7192850.3953170.7544940.020*
C90.7045 (3)0.43003 (6)0.87935 (9)0.0159 (3)
C100.9212 (3)0.47956 (7)0.86014 (10)0.0200 (3)
H10A1.1076920.4611020.8555380.030*
H10B0.8916260.4999110.8042580.030*
H10C0.9049960.5098620.9081340.030*
C110.6700 (3)0.12958 (6)0.92701 (9)0.0132 (2)
C120.5668 (3)0.15332 (6)0.76841 (8)0.0148 (3)
H12A0.7676280.1452250.7646910.018*
H12B0.5169240.1912910.7344930.018*
C130.3974 (3)0.09994 (7)0.72690 (9)0.0184 (3)
H13A0.4534840.0618330.7582230.028*
H13B0.4310280.0960980.6645520.028*
H13C0.1985590.1074720.7311470.028*
C140.3072 (3)0.20499 (6)0.87829 (8)0.0124 (2)
C150.5709 (3)0.42136 (6)0.96368 (9)0.0187 (3)
H150.6213300.4468041.0104040.022*
C160.3657 (3)0.37673 (6)0.98239 (9)0.0183 (3)
H160.2772630.3723091.0407680.022*
N10.6200 (2)0.14275 (5)1.01321 (7)0.0132 (2)
N20.0813 (2)0.29283 (5)0.92183 (7)0.0134 (2)
H2A0.0321930.2805340.8703820.016*
N30.5180 (2)0.16309 (5)0.86255 (7)0.0125 (2)
O10.1706 (2)0.22802 (4)0.81289 (6)0.0156 (2)
O20.4004 (2)0.18827 (4)1.11873 (6)0.0158 (2)
H20.2822270.2153501.1279830.024*
S10.90026 (7)0.07630 (2)0.90407 (2)0.01698 (9)
S20.00427 (8)0.27972 (2)1.09736 (2)0.01633 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0230 (8)0.0181 (7)0.0185 (7)0.0025 (6)0.0010 (6)0.0038 (5)
C20.0157 (7)0.0187 (7)0.0143 (6)0.0026 (5)0.0029 (5)0.0022 (5)
C30.0126 (6)0.0126 (6)0.0137 (6)0.0027 (5)0.0009 (5)0.0000 (5)
C40.0134 (6)0.0123 (6)0.0108 (5)0.0010 (5)0.0011 (5)0.0007 (4)
C50.0133 (6)0.0116 (6)0.0125 (6)0.0027 (5)0.0015 (5)0.0009 (4)
C60.0134 (6)0.0121 (6)0.0143 (6)0.0003 (5)0.0023 (5)0.0002 (5)
C70.0170 (7)0.0159 (6)0.0129 (6)0.0007 (5)0.0016 (5)0.0012 (5)
C80.0167 (7)0.0172 (6)0.0151 (6)0.0008 (5)0.0015 (5)0.0009 (5)
C90.0133 (6)0.0145 (6)0.0201 (6)0.0016 (5)0.0027 (5)0.0025 (5)
C100.0165 (7)0.0179 (7)0.0252 (7)0.0027 (5)0.0008 (6)0.0020 (5)
C110.0120 (6)0.0121 (6)0.0155 (6)0.0027 (5)0.0018 (5)0.0005 (5)
C120.0162 (7)0.0174 (6)0.0116 (6)0.0011 (5)0.0053 (5)0.0003 (5)
C130.0204 (7)0.0205 (7)0.0146 (6)0.0005 (5)0.0034 (5)0.0048 (5)
C140.0123 (6)0.0113 (6)0.0134 (6)0.0024 (5)0.0011 (5)0.0009 (4)
C150.0227 (7)0.0169 (7)0.0171 (6)0.0048 (6)0.0046 (5)0.0014 (5)
C160.0235 (7)0.0183 (7)0.0130 (6)0.0042 (6)0.0005 (5)0.0007 (5)
N10.0132 (6)0.0134 (5)0.0128 (5)0.0002 (4)0.0004 (4)0.0009 (4)
N20.0161 (6)0.0138 (5)0.0105 (5)0.0025 (4)0.0019 (4)0.0006 (4)
N30.0130 (6)0.0133 (5)0.0115 (5)0.0003 (4)0.0023 (4)0.0005 (4)
O10.0188 (5)0.0169 (5)0.0109 (4)0.0030 (4)0.0004 (4)0.0003 (3)
O20.0181 (5)0.0188 (5)0.0105 (4)0.0032 (4)0.0011 (4)0.0006 (4)
S10.01535 (17)0.01646 (17)0.01953 (17)0.00346 (12)0.00381 (13)0.00027 (12)
S20.02104 (18)0.01790 (17)0.01023 (15)0.00360 (13)0.00249 (12)0.00065 (12)
Geometric parameters (Å, º) top
C1—C21.516 (2)C9—C101.5078 (19)
C1—H1A0.9800C10—H10A0.9800
C1—H1B0.9800C10—H10B0.9800
C1—H1C0.9800C10—H10C0.9800
C2—N11.4876 (16)C11—N31.3726 (16)
C2—H2B0.9900C11—N11.3846 (17)
C2—H2C0.9900C11—S11.6639 (14)
C3—O21.2947 (16)C12—N31.4874 (16)
C3—N11.3752 (17)C12—C131.5192 (19)
C3—C41.4038 (17)C12—H12A0.9900
C4—C141.4453 (17)C12—H12B0.9900
C4—C51.4711 (18)C13—H13A0.9800
C5—N21.3370 (16)C13—H13B0.9800
C5—S21.7071 (13)C13—H13C0.9800
C6—C161.3931 (18)C14—O11.2415 (16)
C6—C71.4011 (18)C14—N31.4019 (17)
C6—N21.4164 (17)C15—C161.3942 (19)
C7—C81.3855 (19)C15—H150.9500
C7—H70.9500C16—H160.9500
C8—C91.395 (2)N2—H2A0.8800
C8—H80.9500O2—H20.8400
C9—C151.3885 (19)
C2—C1—H1A109.5H10A—C10—H10C109.5
C2—C1—H1B109.5H10B—C10—H10C109.5
H1A—C1—H1B109.5N3—C11—N1115.75 (11)
C2—C1—H1C109.5N3—C11—S1122.66 (10)
H1A—C1—H1C109.5N1—C11—S1121.58 (10)
H1B—C1—H1C109.5N3—C12—C13112.27 (11)
N1—C2—C1111.91 (11)N3—C12—H12A109.2
N1—C2—H2B109.2C13—C12—H12A109.2
C1—C2—H2B109.2N3—C12—H12B109.2
N1—C2—H2C109.2C13—C12—H12B109.2
C1—C2—H2C109.2H12A—C12—H12B107.9
H2B—C2—H2C107.9C12—C13—H13A109.5
O2—C3—N1113.75 (11)C12—C13—H13B109.5
O2—C3—C4124.99 (12)H13A—C13—H13B109.5
N1—C3—C4121.24 (12)C12—C13—H13C109.5
C3—C4—C14116.88 (12)H13A—C13—H13C109.5
C3—C4—C5122.11 (12)H13B—C13—H13C109.5
C14—C4—C5120.98 (11)O1—C14—N3117.45 (11)
N2—C5—C4115.81 (11)O1—C14—C4124.63 (12)
N2—C5—S2122.21 (10)N3—C14—C4117.92 (11)
C4—C5—S2121.98 (9)C9—C15—C16122.49 (13)
C16—C6—C7118.85 (12)C9—C15—H15118.8
C16—C6—N2126.56 (12)C16—C15—H15118.8
C7—C6—N2114.56 (11)C6—C16—C15119.45 (12)
C8—C7—C6120.49 (12)C6—C16—H16120.3
C8—C7—H7119.8C15—C16—H16120.3
C6—C7—H7119.8C3—N1—C11123.34 (11)
C7—C8—C9121.49 (12)C3—N1—C2117.49 (11)
C7—C8—H8119.3C11—N1—C2119.16 (11)
C9—C8—H8119.3C5—N2—C6133.01 (11)
C15—C9—C8117.22 (13)C5—N2—H2A113.5
C15—C9—C10121.62 (13)C6—N2—H2A113.5
C8—C9—C10121.16 (12)C11—N3—C14124.58 (11)
C9—C10—H10A109.5C11—N3—C12119.10 (11)
C9—C10—H10B109.5C14—N3—C12116.26 (10)
H10A—C10—H10B109.5C3—O2—H2109.5
C9—C10—H10C109.5
O2—C3—C4—C14175.61 (12)C4—C3—N1—C111.66 (19)
N1—C3—C4—C142.86 (19)O2—C3—N1—C21.73 (17)
O2—C3—C4—C52.6 (2)C4—C3—N1—C2179.63 (12)
N1—C3—C4—C5178.90 (12)N3—C11—N1—C32.49 (18)
C3—C4—C5—N2179.38 (12)S1—C11—N1—C3177.43 (10)
C14—C4—C5—N21.21 (18)N3—C11—N1—C2178.82 (11)
C3—C4—C5—S20.13 (18)S1—C11—N1—C21.26 (17)
C14—C4—C5—S2178.04 (10)C1—C2—N1—C389.70 (14)
C16—C6—C7—C80.5 (2)C1—C2—N1—C1189.06 (15)
N2—C6—C7—C8177.64 (12)C4—C5—N2—C6179.88 (13)
C6—C7—C8—C90.2 (2)S2—C5—N2—C60.9 (2)
C7—C8—C9—C151.1 (2)C16—C6—N2—C515.8 (2)
C7—C8—C9—C10178.74 (13)C7—C6—N2—C5166.23 (14)
C3—C4—C14—O1175.27 (12)N1—C11—N3—C145.00 (18)
C5—C4—C14—O13.0 (2)S1—C11—N3—C14174.92 (10)
C3—C4—C14—N34.98 (18)N1—C11—N3—C12177.82 (11)
C5—C4—C14—N3176.76 (11)S1—C11—N3—C122.26 (17)
C8—C9—C15—C161.3 (2)O1—C14—N3—C11173.84 (12)
C10—C9—C15—C16178.54 (14)C4—C14—N3—C116.40 (18)
C7—C6—C16—C150.3 (2)O1—C14—N3—C123.41 (17)
N2—C6—C16—C15177.58 (13)C4—C14—N3—C12176.35 (11)
C9—C15—C16—C60.6 (2)C13—C12—N3—C1185.26 (15)
O2—C3—N1—C11176.97 (12)C13—C12—N3—C1492.15 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C7—H7···O2i0.952.623.3136 (16)130
C13—H13A···S10.982.953.4766 (15)115
C16—H16···S20.952.513.1509 (14)125
N2—H2A···O10.881.792.5671 (15)147
O2—H2···S20.841.992.7802 (10)157
Symmetry code: (i) x1, y+1/2, z1/2.
5-(1-Aminoethylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (A17) top
Crystal data top
C10H15N3O2SF(000) = 1024
Mr = 241.31Dx = 1.400 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 12.8983 (4) ÅCell parameters from 9096 reflections
b = 9.8458 (3) Åθ = 1.7–28.4°
c = 18.2217 (6) ŵ = 0.27 mm1
β = 98.250 (2)°T = 100 K
V = 2290.10 (13) Å3Block, colourless
Z = 80.19 × 0.13 × 0.09 mm
Data collection top
Bruker APEXII CCD
diffractometer
5036 independent reflections
Radiation source: sealed tube4323 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
φ and ω scansθmax = 27.2°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 1616
Tmin = 0.941, Tmax = 0.985k = 1212
14727 measured reflectionsl = 2322
Refinement top
Refinement on F23 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.088 w = 1/[σ2(Fo2) + (0.0456P)2 + 0.8588P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.004
5036 reflectionsΔρmax = 0.28 e Å3
291 parametersΔρmin = 0.27 e Å3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C60.61243 (11)0.27480 (14)0.36078 (8)0.0203 (3)
H6A0.65190.27750.31870.030*
H6B0.60930.36620.38160.030*
H6C0.54120.24220.34400.030*
C70.66566 (10)0.18105 (13)0.41878 (7)0.0150 (3)
C100.68959 (10)0.07191 (13)0.54211 (7)0.0149 (3)
C40.72421 (11)0.01292 (14)0.66991 (8)0.0191 (3)
H4A0.71070.02300.71840.023*
H4B0.79710.01080.66400.023*
C50.71329 (12)0.16651 (15)0.67012 (9)0.0248 (3)
H5A0.76290.20470.71060.037*
H5B0.64170.19090.67720.037*
H5C0.72820.20310.62270.037*
C30.55336 (10)0.09224 (13)0.62285 (7)0.0156 (3)
C90.53259 (10)0.21474 (13)0.50361 (7)0.0155 (3)
C20.38748 (10)0.20954 (14)0.57743 (8)0.0178 (3)
H2A0.35500.13770.60460.021*
H2B0.34500.21960.52800.021*
C10.38662 (11)0.34275 (15)0.61955 (9)0.0234 (3)
H1A0.31430.36700.62460.035*
H1B0.42750.33260.66890.035*
H1C0.41750.41450.59230.035*
C200.15999 (10)0.69458 (13)0.29638 (7)0.0147 (3)
C130.00875 (10)0.80458 (13)0.33995 (8)0.0164 (3)
C140.00593 (10)0.80558 (14)0.47372 (8)0.0191 (3)
H14A0.03330.89880.46430.023*
H14B0.04660.80810.51900.023*
C150.09521 (11)0.71255 (17)0.48682 (9)0.0278 (3)
H15A0.12690.74590.52920.042*
H15B0.14810.71120.44250.042*
H15C0.06830.62040.49730.042*
C170.27977 (10)0.55276 (13)0.38352 (8)0.0157 (3)
C160.34694 (11)0.51622 (15)0.32607 (8)0.0206 (3)
H16A0.40170.45280.34740.031*
H16B0.37940.59850.30950.031*
H16C0.30370.47330.28370.031*
C190.13125 (10)0.67181 (13)0.42765 (7)0.0149 (3)
C120.02386 (11)0.79835 (15)0.20565 (8)0.0209 (3)
H12A0.05350.80500.19950.025*
H12B0.04220.72360.17350.025*
C110.06788 (13)0.93049 (16)0.18012 (9)0.0276 (3)
H11A0.03900.94730.12820.041*
H11B0.04861.00540.21090.041*
H11C0.14440.92400.18480.041*
C80.62892 (10)0.15566 (13)0.48761 (7)0.0146 (3)
N20.65158 (8)0.05361 (11)0.61006 (6)0.0152 (2)
N30.49530 (8)0.16758 (11)0.56810 (6)0.0150 (2)
N10.74982 (9)0.12103 (12)0.40227 (6)0.0173 (2)
H1D0.78460.06400.43390.021*
H1E0.77160.13770.35960.021*
N50.06334 (8)0.76423 (11)0.28415 (6)0.0157 (2)
N60.04578 (8)0.76099 (11)0.41021 (6)0.0154 (2)
C180.19109 (10)0.64012 (13)0.36918 (7)0.0145 (3)
N40.30665 (9)0.49831 (12)0.44921 (7)0.0197 (3)
H4C0.26970.51560.48520.024*
H4D0.36160.44450.45730.024*
O10.47924 (7)0.29948 (10)0.46500 (5)0.0213 (2)
O20.77401 (7)0.01732 (10)0.53471 (5)0.0197 (2)
O30.20935 (7)0.68444 (10)0.24372 (5)0.0187 (2)
O40.15024 (7)0.62872 (10)0.49193 (5)0.0192 (2)
S10.50759 (3)0.05125 (4)0.70094 (2)0.02191 (10)
S20.09755 (3)0.90311 (4)0.32209 (2)0.02713 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C60.0229 (7)0.0194 (7)0.0191 (7)0.0044 (6)0.0048 (5)0.0033 (5)
C70.0151 (6)0.0133 (6)0.0162 (6)0.0016 (5)0.0008 (5)0.0027 (5)
C100.0147 (6)0.0127 (6)0.0168 (7)0.0016 (5)0.0009 (5)0.0017 (5)
C40.0177 (7)0.0214 (7)0.0165 (7)0.0002 (5)0.0030 (5)0.0030 (5)
C50.0236 (7)0.0215 (7)0.0280 (8)0.0024 (6)0.0004 (6)0.0059 (6)
C30.0176 (6)0.0138 (6)0.0151 (6)0.0024 (5)0.0014 (5)0.0035 (5)
C90.0154 (6)0.0152 (6)0.0155 (6)0.0002 (5)0.0010 (5)0.0030 (5)
C20.0128 (6)0.0205 (7)0.0203 (7)0.0007 (5)0.0031 (5)0.0041 (5)
C10.0180 (7)0.0243 (7)0.0278 (8)0.0030 (6)0.0028 (6)0.0085 (6)
C200.0137 (6)0.0114 (6)0.0186 (6)0.0022 (5)0.0014 (5)0.0028 (5)
C130.0145 (6)0.0131 (6)0.0209 (7)0.0002 (5)0.0005 (5)0.0020 (5)
C140.0174 (6)0.0205 (7)0.0202 (7)0.0027 (5)0.0050 (5)0.0058 (5)
C150.0203 (7)0.0337 (8)0.0313 (8)0.0015 (6)0.0098 (6)0.0033 (7)
C170.0139 (6)0.0129 (6)0.0201 (7)0.0017 (5)0.0013 (5)0.0022 (5)
C160.0170 (7)0.0216 (7)0.0238 (8)0.0052 (5)0.0050 (5)0.0003 (6)
C190.0126 (6)0.0129 (6)0.0190 (7)0.0012 (5)0.0012 (5)0.0012 (5)
C120.0205 (7)0.0234 (7)0.0171 (7)0.0026 (6)0.0032 (5)0.0001 (6)
C110.0313 (8)0.0261 (8)0.0238 (8)0.0019 (6)0.0017 (6)0.0066 (6)
C80.0143 (6)0.0135 (6)0.0159 (6)0.0002 (5)0.0019 (5)0.0011 (5)
N20.0148 (5)0.0154 (5)0.0146 (6)0.0007 (4)0.0000 (4)0.0010 (4)
N30.0134 (5)0.0153 (5)0.0165 (6)0.0008 (4)0.0028 (4)0.0019 (4)
N10.0169 (6)0.0184 (6)0.0171 (6)0.0029 (4)0.0046 (4)0.0009 (5)
N50.0153 (5)0.0150 (5)0.0163 (6)0.0016 (4)0.0001 (4)0.0001 (4)
N60.0133 (5)0.0144 (5)0.0184 (6)0.0015 (4)0.0021 (4)0.0029 (4)
C180.0132 (6)0.0131 (6)0.0171 (6)0.0004 (5)0.0022 (5)0.0018 (5)
N40.0169 (6)0.0214 (6)0.0205 (6)0.0064 (5)0.0020 (5)0.0019 (5)
O10.0192 (5)0.0241 (5)0.0209 (5)0.0093 (4)0.0035 (4)0.0046 (4)
O20.0156 (4)0.0216 (5)0.0217 (5)0.0056 (4)0.0023 (4)0.0026 (4)
O30.0189 (5)0.0208 (5)0.0171 (5)0.0006 (4)0.0050 (4)0.0005 (4)
O40.0193 (5)0.0221 (5)0.0165 (5)0.0034 (4)0.0036 (4)0.0019 (4)
S10.02434 (19)0.02587 (19)0.01656 (18)0.00022 (14)0.00644 (14)0.00183 (14)
S20.02287 (19)0.0292 (2)0.0281 (2)0.01446 (15)0.00076 (15)0.00179 (16)
Geometric parameters (Å, º) top
C6—C71.4940 (18)C20—C181.4338 (19)
C6—H6A0.9800C13—N61.3695 (18)
C6—H6B0.9800C13—N51.3758 (17)
C6—H6C0.9800C13—S21.6729 (13)
C7—N11.3083 (17)C14—N61.4828 (16)
C7—C81.4251 (18)C14—C151.517 (2)
C10—O21.2390 (16)C14—H14A0.9900
C10—N21.4071 (17)C14—H14B0.9900
C10—C81.4337 (18)C15—H15A0.9800
C4—N21.4842 (17)C15—H15B0.9800
C4—C51.519 (2)C15—H15C0.9800
C4—H4A0.9900C17—N41.3120 (18)
C4—H4B0.9900C17—C181.4250 (18)
C5—H5A0.9800C17—C161.4953 (18)
C5—H5B0.9800C16—H16A0.9800
C5—H5C0.9800C16—H16B0.9800
C3—N21.3743 (17)C16—H16C0.9800
C3—N31.3754 (18)C19—O41.2367 (16)
C3—S11.6667 (14)C19—N61.4095 (16)
C9—O11.2352 (16)C19—C181.4367 (17)
C9—N31.4107 (17)C12—N51.4864 (17)
C9—C81.4390 (18)C12—C111.519 (2)
C2—N31.4838 (16)C12—H12A0.9900
C2—C11.5204 (19)C12—H12B0.9900
C2—H2A0.9900C11—H11A0.9800
C2—H2B0.9900C11—H11B0.9800
C1—H1A0.9800C11—H11C0.9800
C1—H1B0.9800N1—H1D0.8800
C1—H1C0.9800N1—H1E0.8800
C20—O31.2294 (16)N4—H4C0.8800
C20—N51.4123 (16)N4—H4D0.8800
C7—C6—H6A109.5C14—C15—H15A109.5
C7—C6—H6B109.5C14—C15—H15B109.5
H6A—C6—H6B109.5H15A—C15—H15B109.5
C7—C6—H6C109.5C14—C15—H15C109.5
H6A—C6—H6C109.5H15A—C15—H15C109.5
H6B—C6—H6C109.5H15B—C15—H15C109.5
N1—C7—C8120.98 (12)N4—C17—C18120.92 (12)
N1—C7—C6115.39 (12)N4—C17—C16115.89 (12)
C8—C7—C6123.62 (12)C18—C17—C16123.19 (12)
O2—C10—N2117.57 (12)C17—C16—H16A109.5
O2—C10—C8125.10 (12)C17—C16—H16B109.5
N2—C10—C8117.30 (11)H16A—C16—H16B109.5
N2—C4—C5113.10 (11)C17—C16—H16C109.5
N2—C4—H4A109.0H16A—C16—H16C109.5
C5—C4—H4A109.0H16B—C16—H16C109.5
N2—C4—H4B109.0O4—C19—N6118.00 (12)
C5—C4—H4B109.0O4—C19—C18124.98 (12)
H4A—C4—H4B107.8N6—C19—C18117.01 (11)
C4—C5—H5A109.5N5—C12—C11113.38 (12)
C4—C5—H5B109.5N5—C12—H12A108.9
H5A—C5—H5B109.5C11—C12—H12A108.9
C4—C5—H5C109.5N5—C12—H12B108.9
H5A—C5—H5C109.5C11—C12—H12B108.9
H5B—C5—H5C109.5H12A—C12—H12B107.7
N2—C3—N3116.45 (11)C12—C11—H11A109.5
N2—C3—S1121.73 (10)C12—C11—H11B109.5
N3—C3—S1121.81 (10)H11A—C11—H11B109.5
O1—C9—N3117.90 (12)C12—C11—H11C109.5
O1—C9—C8125.76 (13)H11A—C11—H11C109.5
N3—C9—C8116.31 (11)H11B—C11—H11C109.5
N3—C2—C1111.89 (11)C7—C8—C10119.54 (11)
N3—C2—H2A109.2C7—C8—C9120.88 (12)
C1—C2—H2A109.2C10—C8—C9119.57 (12)
N3—C2—H2B109.2C3—N2—C10124.04 (11)
C1—C2—H2B109.2C3—N2—C4119.84 (11)
H2A—C2—H2B107.9C10—N2—C4116.12 (11)
C2—C1—H1A109.5C3—N3—C9124.50 (11)
C2—C1—H1B109.5C3—N3—C2119.26 (11)
H1A—C1—H1B109.5C9—N3—C2116.17 (11)
C2—C1—H1C109.5C7—N1—H1D120.0
H1A—C1—H1C109.5C7—N1—H1E120.0
H1B—C1—H1C109.5H1D—N1—H1E120.0
O3—C20—N5117.43 (12)C13—N5—C20123.88 (11)
O3—C20—C18125.76 (12)C13—N5—C12120.33 (11)
N5—C20—C18116.81 (11)C20—N5—C12115.74 (11)
N6—C13—N5116.97 (11)C13—N6—C19124.23 (11)
N6—C13—S2121.99 (10)C13—N6—C14120.08 (11)
N5—C13—S2121.04 (10)C19—N6—C14115.67 (11)
N6—C14—C15112.37 (11)C17—C18—C20120.40 (12)
N6—C14—H14A109.1C17—C18—C19119.85 (12)
C15—C14—H14A109.1C20—C18—C19119.74 (11)
N6—C14—H14B109.1C17—N4—H4C120.0
C15—C14—H14B109.1C17—N4—H4D120.0
H14A—C14—H14B107.9H4C—N4—H4D120.0
N1—C7—C8—C105.16 (19)N6—C13—N5—C207.27 (18)
C6—C7—C8—C10175.35 (12)S2—C13—N5—C20172.41 (10)
N1—C7—C8—C9175.84 (12)N6—C13—N5—C12175.36 (11)
C6—C7—C8—C93.6 (2)S2—C13—N5—C124.96 (17)
O2—C10—C8—C70.1 (2)O3—C20—N5—C13167.99 (12)
N2—C10—C8—C7177.99 (11)C18—C20—N5—C1312.88 (18)
O2—C10—C8—C9179.13 (12)O3—C20—N5—C129.49 (17)
N2—C10—C8—C91.02 (18)C18—C20—N5—C12169.64 (11)
O1—C9—C8—C77.1 (2)C11—C12—N5—C1392.32 (15)
N3—C9—C8—C7170.88 (11)C11—C12—N5—C2085.25 (15)
O1—C9—C8—C10171.89 (13)N5—C13—N6—C194.06 (18)
N3—C9—C8—C1010.12 (18)S2—C13—N6—C19176.25 (10)
N3—C3—N2—C108.11 (18)N5—C13—N6—C14177.13 (11)
S1—C3—N2—C10172.50 (10)S2—C13—N6—C142.55 (17)
N3—C3—N2—C4172.44 (11)O4—C19—N6—C13172.51 (12)
S1—C3—N2—C46.95 (17)C18—C19—N6—C138.68 (18)
O2—C10—N2—C3170.97 (12)O4—C19—N6—C146.34 (17)
C8—C10—N2—C310.78 (19)C18—C19—N6—C14172.46 (11)
O2—C10—N2—C48.51 (17)C15—C14—N6—C1388.19 (15)
C8—C10—N2—C4169.74 (11)C15—C14—N6—C1990.71 (14)
C5—C4—N2—C389.41 (15)N4—C17—C18—C20177.45 (12)
C5—C4—N2—C1090.08 (14)C16—C17—C18—C202.01 (19)
N2—C3—N3—C94.72 (18)N4—C17—C18—C191.37 (19)
S1—C3—N3—C9174.67 (10)C16—C17—C18—C19179.17 (12)
N2—C3—N3—C2178.38 (11)O3—C20—C18—C177.7 (2)
S1—C3—N3—C22.23 (17)N5—C20—C18—C17171.32 (11)
O1—C9—N3—C3168.30 (12)O3—C20—C18—C19173.46 (12)
C8—C9—N3—C313.55 (18)N5—C20—C18—C197.50 (18)
O1—C9—N3—C28.69 (17)O4—C19—C18—C170.0 (2)
C8—C9—N3—C2169.46 (11)N6—C19—C18—C17178.75 (11)
C1—C2—N3—C387.13 (15)O4—C19—C18—C20178.86 (12)
C1—C2—N3—C990.02 (14)N6—C19—C18—C202.43 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6A···O3i0.982.433.3103 (17)149
N1—H1D···O20.881.922.5977 (15)133
N1—H1E···O3i0.881.992.8540 (15)168
N4—H4C···O40.881.922.6029 (15)133
N4—H4D···O10.882.072.9473 (15)172
Symmetry code: (i) x+1, y1/2, z+1/2.
5-(1-Aminopropylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (A18) top
Crystal data top
C11H17N3O2SDx = 1.383 Mg m3
Mr = 255.33Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 5433 reflections
a = 4.9625 (3) Åθ = 2.6–27.3°
b = 10.6358 (7) ŵ = 0.26 mm1
c = 23.2402 (15) ÅT = 100 K
V = 1226.62 (14) Å3Rod, orange
Z = 40.25 × 0.11 × 0.09 mm
F(000) = 544
Data collection top
Bruker APEXII CCD
diffractometer
10534 independent reflections
Radiation source: sealed tube9991 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.000
φ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Bruker, 2012)
h = 66
Tmin = 0.924, Tmax = 0.988k = 1313
10534 measured reflectionsl = 3028
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.032 w = 1/[σ2(Fo2) + (0.0273P)2 + 0.4988P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076(Δ/σ)max = 0.001
S = 1.03Δρmax = 0.28 e Å3
10534 reflectionsΔρmin = 0.22 e Å3
154 parametersAbsolute structure: Flack x determined using 1038 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute structure parameter: 0.02 (3)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.6440 (6)0.8030 (2)0.90953 (10)0.0193 (5)
H1A0.6145190.8782310.9330810.029*
H1B0.8307200.7747050.9139550.029*
H1C0.6093230.8230200.8690340.029*
C20.4537 (5)0.6994 (2)0.92894 (10)0.0176 (6)
H2A0.4868960.6806270.9700530.021*
H2B0.2653880.7289660.9251090.021*
C30.6710 (5)0.4948 (2)0.91284 (9)0.0165 (5)
C40.8881 (5)0.2876 (2)0.89628 (11)0.0187 (6)
H4A1.0434890.3260640.9163890.022*
H4B0.9565080.2454980.8612220.022*
C50.7578 (6)0.1907 (3)0.93530 (11)0.0259 (7)
H5A0.8905150.1262060.9454860.039*
H5B0.6927910.2319000.9703760.039*
H5C0.6058650.1513850.9152440.039*
C60.1787 (6)0.4847 (2)0.68889 (11)0.0237 (6)
H6A0.2972940.5530480.6763350.035*
H6B0.0566860.4617760.6574300.035*
H6C0.2877020.4115080.6996110.035*
C70.0142 (5)0.5278 (2)0.74073 (10)0.0159 (5)
H7A0.0898650.6033440.7295090.019*
H7B0.1405420.5532090.7715790.019*
C80.1772 (5)0.4330 (2)0.76485 (10)0.0147 (5)
C90.3485 (5)0.4573 (2)0.81314 (10)0.0135 (5)
C100.5338 (5)0.3619 (2)0.83171 (10)0.0150 (5)
C110.3302 (5)0.5736 (2)0.84439 (10)0.0145 (5)
N10.4895 (4)0.58329 (19)0.89474 (8)0.0146 (5)
N20.6952 (4)0.38770 (18)0.87954 (8)0.0147 (5)
O10.5626 (4)0.25808 (16)0.80789 (7)0.0204 (4)
O20.1876 (4)0.66376 (16)0.83154 (7)0.0205 (4)
N30.1851 (5)0.32251 (19)0.73951 (8)0.0185 (5)
H3A0.2953820.2639960.7522500.022*
H3B0.0802060.3070960.7098090.022*
S10.85678 (15)0.51436 (6)0.97179 (3)0.02579 (18)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0194 (14)0.0181 (13)0.0205 (13)0.0008 (12)0.0006 (12)0.0028 (10)
C20.0162 (13)0.0207 (14)0.0158 (12)0.0013 (11)0.0010 (10)0.0055 (11)
C30.0150 (12)0.0178 (13)0.0168 (12)0.0028 (12)0.0009 (9)0.0027 (10)
C40.0165 (14)0.0193 (14)0.0203 (13)0.0043 (11)0.0024 (11)0.0031 (10)
C50.0295 (17)0.0211 (14)0.0269 (15)0.0008 (12)0.0015 (12)0.0086 (12)
C60.0252 (15)0.0207 (14)0.0251 (13)0.0009 (13)0.0074 (11)0.0006 (12)
C70.0141 (12)0.0152 (13)0.0183 (12)0.0005 (11)0.0011 (10)0.0013 (10)
C80.0140 (13)0.0143 (12)0.0157 (12)0.0003 (11)0.0036 (10)0.0026 (10)
C90.0126 (12)0.0140 (12)0.0138 (11)0.0001 (10)0.0018 (10)0.0008 (9)
C100.0135 (13)0.0168 (13)0.0149 (12)0.0017 (10)0.0022 (10)0.0027 (10)
C110.0120 (13)0.0170 (12)0.0143 (12)0.0022 (11)0.0007 (10)0.0019 (10)
N10.0142 (11)0.0155 (11)0.0141 (11)0.0002 (9)0.0003 (9)0.0005 (9)
N20.0134 (11)0.0133 (10)0.0173 (10)0.0001 (9)0.0014 (9)0.0025 (8)
O10.0221 (11)0.0159 (10)0.0232 (10)0.0044 (8)0.0022 (8)0.0034 (8)
O20.0219 (11)0.0170 (9)0.0226 (9)0.0058 (8)0.0049 (8)0.0016 (7)
N30.0225 (13)0.0158 (11)0.0173 (10)0.0022 (10)0.0053 (9)0.0017 (9)
S10.0308 (4)0.0239 (4)0.0227 (3)0.0017 (3)0.0131 (3)0.0009 (3)
Geometric parameters (Å, º) top
C1—C21.520 (4)C6—C71.526 (3)
C1—H1A0.9800C6—H6A0.9800
C1—H1B0.9800C6—H6B0.9800
C1—H1C0.9800C6—H6C0.9800
C2—N11.480 (3)C7—C81.494 (3)
C2—H2A0.9900C7—H7A0.9900
C2—H2B0.9900C7—H7B0.9900
C3—N11.369 (3)C8—N31.315 (3)
C3—N21.383 (3)C8—C91.432 (3)
C3—S11.664 (2)C9—C101.436 (3)
C4—N21.483 (3)C9—C111.437 (3)
C4—C51.518 (3)C10—O11.243 (3)
C4—H4A0.9900C10—N21.398 (3)
C4—H4B0.9900C11—O21.228 (3)
C5—H5A0.9800C11—N11.416 (3)
C5—H5B0.9800N3—H3A0.8800
C5—H5C0.9800N3—H3B0.8800
C2—C1—H1A109.5C7—C6—H6C109.5
C2—C1—H1B109.5H6A—C6—H6C109.5
H1A—C1—H1B109.5H6B—C6—H6C109.5
C2—C1—H1C109.5C8—C7—C6115.7 (2)
H1A—C1—H1C109.5C8—C7—H7A108.4
H1B—C1—H1C109.5C6—C7—H7A108.4
N1—C2—C1111.8 (2)C8—C7—H7B108.4
N1—C2—H2A109.3C6—C7—H7B108.4
C1—C2—H2A109.3H7A—C7—H7B107.4
N1—C2—H2B109.3N3—C8—C9119.7 (2)
C1—C2—H2B109.3N3—C8—C7117.0 (2)
H2A—C2—H2B107.9C9—C8—C7123.3 (2)
N1—C3—N2116.8 (2)C8—C9—C10119.2 (2)
N1—C3—S1122.12 (18)C8—C9—C11121.0 (2)
N2—C3—S1121.03 (19)C10—C9—C11119.8 (2)
N2—C4—C5111.7 (2)O1—C10—N2117.6 (2)
N2—C4—H4A109.3O1—C10—C9124.6 (2)
C5—C4—H4A109.3N2—C10—C9117.8 (2)
N2—C4—H4B109.3O2—C11—N1117.8 (2)
C5—C4—H4B109.3O2—C11—C9125.8 (2)
H4A—C4—H4B107.9N1—C11—C9116.4 (2)
C4—C5—H5A109.5C3—N1—C11124.9 (2)
C4—C5—H5B109.5C3—N1—C2119.2 (2)
H5A—C5—H5B109.5C11—N1—C2115.9 (2)
C4—C5—H5C109.5C3—N2—C10123.9 (2)
H5A—C5—H5C109.5C3—N2—C4120.0 (2)
H5B—C5—H5C109.5C10—N2—C4115.9 (2)
C7—C6—H6A109.5C8—N3—H3A120.0
C7—C6—H6B109.5C8—N3—H3B120.0
H6A—C6—H6B109.5H3A—N3—H3B120.0
C6—C7—C8—N30.2 (3)S1—C3—N1—C20.8 (3)
C6—C7—C8—C9179.6 (2)O2—C11—N1—C3175.6 (2)
N3—C8—C9—C102.3 (4)C9—C11—N1—C35.1 (3)
C7—C8—C9—C10177.5 (2)O2—C11—N1—C23.7 (3)
N3—C8—C9—C11175.3 (2)C9—C11—N1—C2175.6 (2)
C7—C8—C9—C114.9 (4)C1—C2—N1—C390.0 (3)
C8—C9—C10—O11.7 (4)C1—C2—N1—C1189.4 (3)
C11—C9—C10—O1179.4 (2)N1—C3—N2—C104.6 (3)
C8—C9—C10—N2179.0 (2)S1—C3—N2—C10175.80 (18)
C11—C9—C10—N21.3 (3)N1—C3—N2—C4179.9 (2)
C8—C9—C11—O25.3 (4)S1—C3—N2—C40.3 (3)
C10—C9—C11—O2177.1 (2)O1—C10—N2—C3174.9 (2)
C8—C9—C11—N1174.0 (2)C9—C10—N2—C35.7 (3)
C10—C9—C11—N13.7 (3)O1—C10—N2—C40.8 (3)
N2—C3—N1—C111.1 (3)C9—C10—N2—C4178.6 (2)
S1—C3—N1—C11178.49 (19)C5—C4—N2—C390.3 (3)
N2—C3—N1—C2179.6 (2)C5—C4—N2—C1085.6 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1A···S1i0.982.803.662 (3)147
C7—H7A···O1ii0.992.543.507 (3)166
N3—H3A···O10.881.852.550 (3)135
N3—H3B···O2iii0.882.243.000 (3)145
Symmetry codes: (i) x1/2, y+3/2, z+2; (ii) x+1, y+1/2, z+3/2; (iii) x, y1/2, z+3/2.
RMSD (r.m.s. deviation) values of fitted atoms of PDETBA and dihedral angles (°) between PDETBAPENOL, PDETBAPENAMINE and PDETBAPTHIOAMIDE observed in A01, A02, A06, A13, A17 and A18 top
CompoundRMSD of fitted atoms of PDETBAaDihedral angle [PDETBAPENOLb/PENAMINEc/PTHIOAMIDEd]
A010.01876.3 (1)
A020.02707.3 (2)
A060.01178.7 (2)
A130.01710.2 (2)
A170.0544, 0.04657.9 (2), 5.3 (2)
A180.02455.6 (2)
Notes: (a) Atoms used to define PDETBA: (A01) C3–C6–C7–C8–N1–N2; (A02) C4–C5–C9–N2–C8–N1; (A06) C8–C3–C6–N2–N1–C7; (A13) C3–C4–C11–C14–N1–N3; (A17) C3–C9–C10–C8–N3–N2; (A18) C3–C9–C10–C11–N1–N2. (b) Atoms used to define PENOL: (A01) C9–C10–O3; (A02) C1–C2–C3–O3; (A06) C9–C10–O3. (c) Atoms used to define PENAMINE: (A17) C6–C7–C8–N1; (A18) C6–C7–C8–N3. (d) Atoms used to define PTHIOAMIDE: (A13) C5–N2–S2.
Selected bond parameters (Å) observed in A01, A02, A06, A17 and A18 top
Bond parameterA01A02A06A17A18
Ccarbonyl—Ocarbonyla1.247 (2)1.257 (2)1.250 (2)1.239 (2) 1.237 (2)1.242 (2)
Ccarbonyl—Cethyleneb1.435 (2)1.430 (3)1.404 (2)1.434 (2) 1.437 (2)1.436 (3)
Cethylene—Cenol/enaminec1.398 (2)1.406 (3)1.394 (2)1.425 (2) 1.425 (2)1.430 (3)
Cenol/enamine—Oenol/Nenamined1.309 (2)1.301 (2)1.260 (2)1.308 (2) 1.312 (2)1.314 (2)
Notes: (a) A01 = C6—O2; A02 = C4—O2; A06 = C2—O6; A17 = C10—O2 and C19—O4; A18 = C10—O1; (b) A01 = C6—C7; A02 = C4—C5; A06 = C6—C7; A17 = C10—C8 and C19—C18; A18 = C10—C9; (c) A01 = C7—C8; A02 = C5—C3; A06 = C7—C9; A17 = C8—C7 and C18—C17; A18 = C9—C8; (d) A01 = C9—O3; A02 = C3—O3; A06 = C9—O3; A17 = C7—N1 and C17—N4; A18 = C8—N3.
Selected hydrogen-bonding pattern observed in A01, A02, A06, A17 and A18 top
D—H···AD—HH···AD···AD—H···A
A01
C10—H10A···S1i0.982.883.8316 (14)163
O3—H3···O20.841.712.4756 (13)150
A02
C2—H2A···O2i0.992.563.384 (2)140
C6—H6A···O1ii0.992.573.440 (2)146
C11—H11B···O2iii0.992.563.539 (2)170
O3—H3···O20.841.672.4395 (17)151
A06
C11—H11···N2i1.002.633.613 (3)166
C18—H18A···S1ii0.982.853.760 (2)154
N3—H3···S1i0.83 (1)2.87 (1)3.6957 (17)172 (2)
O2—H2H···O30.86 (1)1.59 (1)2.3723 (19)150 (1)
O3—H1H···O20.86 (1)1.56 (1)2.3723 (19)155 (1)
A13
N2—H2A···O10.881.792.5671 (15)147
O2—H2···S20.841.992.7802 (10)157
A17
C6—H6A···O3i0.982.433.3103 (17)149
N1—H1E···O3i0.881.992.8540 (15)168
N4—H4D···O10.882.072.9473 (15)172
A18
C1—H1A···S1i0.982.803.661 (2)147
C7—H7A···O1ii0.992.543.505 (2)166
N3—H3B···O2iii0.882.242.999 (2)145
Symmetry codes for A01: (i) x-1/2, -y+3/2, z-1/2; for A02: (i) -x, y+1/2, -z+1; (ii) -x+1, y-1/2, -z+1; (iii) -x+1, y+1/2, -z+1; for A06: (i) -x+1, y-1/2, -z+3/2; (ii) -x+3/2, -y+2, z-1/2; for A17: (i) -x+1, y-1/2, -z+1/2; for A18: (i) x-1/2, -y+3/2, -z+2; (ii) -x+1, y+1/2, -z+3/2; (iii) -x, y-1/2, -z+3/2.
Total energy and frontier orbital energy [B3LYP/6-311++G(d,p)] for A01 top
DFT (keto form)DFT (enol form)
Etotala-1123.12965976-1123.15077113
EHOMO-0.24121-0.23291
ELUMO-0.09332-0.09290
ΔEb0.147890.14001
Notes: (a) 1 Hartree = 4.35974417 × 10-18 J = 27.2113845 eV; (b) ΔE = ELUMO - EHOMO.
Calculated reaction profile using DFT [B3LYP/6-311++G(d,p)] top
Relative Energies (kcal mol-1)
Keto form0
Transition State43.51
Enol form-11.54
 

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