Crystal structure, spectroscopic studies and theoretical studies of thio­barbituric acid derivatives: understanding the hydrogen-bonding patterns

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.

Computing details

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)

Crystal data

C10H14N2O3S	F(000) = 512
Mr = 242.29	Dx = 1.430 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.6212 (1) Å	Cell parameters from 8036 reflections
b = 12.5742 (4) Å	θ = 2.7–28.3°
c = 19.3936 (6) Å	µ = 0.28 mm^−1
β = 92.869 (1)°	T = 100 K
V = 1125.51 (6) Å^3	Rod, colourless
Z = 4	0.29 × 0.23 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	2704 independent reflections
Radiation source: sealed tube	2309 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
φ and ω scans	θmax = 28.3°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −5→6
Tmin = 0.911, Tmax = 0.978	k = −16→15
14896 measured reflections	l = −25→24

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.030	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.041P)^2 + 0.5533P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.002
2704 reflections	Δρmax = 0.40 e Å^−3
146 parameters	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7202 (3)	0.48420 (11)	0.60194 (7)	0.0266 (3)
H1A	0.8478	0.4238	0.6134	0.040*
H1B	0.5607	0.4853	0.6334	0.040*
H1C	0.6415	0.4771	0.5543	0.040*
C2	0.8914 (3)	0.58714 (10)	0.60935 (7)	0.0210 (3)
H2A	0.9735	0.5935	0.6573	0.025*
H2B	1.0545	0.5853	0.5781	0.025*
C3	0.5442 (3)	0.72435 (9)	0.64289 (6)	0.0160 (2)
C4	0.2000 (3)	0.86382 (11)	0.67718 (7)	0.0221 (3)
H4A	0.1216	0.8095	0.7082	0.027*
H4B	0.0344	0.9021	0.6543	0.027*
C5	0.3853 (4)	0.94198 (11)	0.71960 (8)	0.0302 (3)
H5A	0.2676	0.9758	0.7541	0.045*
H5B	0.5475	0.9041	0.7430	0.045*
H5C	0.4603	0.9965	0.6891	0.045*
C6	0.3421 (3)	0.85049 (10)	0.55737 (6)	0.0174 (2)
C7	0.5078 (3)	0.80209 (9)	0.50516 (6)	0.0170 (2)
C8	0.7076 (3)	0.71693 (10)	0.52324 (6)	0.0183 (2)
C9	0.4614 (3)	0.83582 (10)	0.43682 (7)	0.0191 (2)
C10	0.6033 (3)	0.79100 (11)	0.37626 (7)	0.0251 (3)
H10A	0.4933	0.8115	0.3338	0.038*
H10B	0.6090	0.7133	0.3799	0.038*
H10C	0.8013	0.8186	0.3751	0.038*
N1	0.7069 (2)	0.68092 (8)	0.59257 (5)	0.0165 (2)
N2	0.3693 (2)	0.81041 (8)	0.62405 (5)	0.0167 (2)
O1	0.8729 (2)	0.67545 (8)	0.48428 (5)	0.0281 (2)
O2	0.1740 (2)	0.92637 (7)	0.54481 (5)	0.0236 (2)
O3	0.2780 (2)	0.91243 (8)	0.42115 (5)	0.0240 (2)
H3	0.2035	0.9341	0.4572	0.036*
S1	0.55504 (7)	0.67705 (2)	0.72282 (2)	0.02091 (10)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0310 (7)	0.0206 (6)	0.0278 (7)	0.0059 (5)	−0.0021 (5)	−0.0034 (5)
C2	0.0181 (6)	0.0226 (6)	0.0219 (6)	0.0061 (5)	−0.0021 (5)	0.0006 (5)
C3	0.0139 (5)	0.0162 (5)	0.0179 (6)	−0.0027 (4)	−0.0008 (4)	−0.0016 (4)
C4	0.0217 (6)	0.0239 (6)	0.0213 (6)	0.0049 (5)	0.0070 (5)	−0.0015 (5)
C5	0.0407 (9)	0.0231 (7)	0.0272 (7)	0.0010 (6)	0.0064 (6)	−0.0074 (5)
C6	0.0152 (6)	0.0182 (5)	0.0188 (6)	−0.0015 (4)	−0.0010 (4)	−0.0007 (4)
C7	0.0153 (6)	0.0188 (6)	0.0167 (6)	−0.0015 (4)	0.0000 (4)	−0.0001 (4)
C8	0.0165 (6)	0.0204 (6)	0.0178 (6)	−0.0007 (4)	0.0004 (4)	−0.0002 (5)
C9	0.0162 (6)	0.0214 (6)	0.0194 (6)	−0.0033 (4)	−0.0008 (4)	0.0009 (5)
C10	0.0277 (7)	0.0304 (7)	0.0170 (6)	0.0007 (5)	0.0007 (5)	0.0005 (5)
N1	0.0150 (5)	0.0175 (5)	0.0170 (5)	0.0019 (4)	−0.0004 (4)	0.0003 (4)
N2	0.0162 (5)	0.0175 (5)	0.0164 (5)	0.0014 (4)	0.0017 (4)	−0.0009 (4)
O1	0.0285 (5)	0.0351 (6)	0.0214 (5)	0.0119 (4)	0.0075 (4)	0.0014 (4)
O2	0.0239 (5)	0.0232 (5)	0.0235 (5)	0.0076 (4)	−0.0008 (4)	0.0018 (4)
O3	0.0247 (5)	0.0271 (5)	0.0200 (5)	0.0036 (4)	−0.0008 (4)	0.0028 (4)
S1	0.02501 (18)	0.02170 (17)	0.01597 (16)	−0.00059 (11)	0.00046 (11)	0.00196 (11)

Geometric parameters (Å, º)

C1—C2	1.5202 (19)	C5—H5B	0.9800
C1—H1A	0.9800	C5—H5C	0.9800
C1—H1B	0.9800	C6—O2	1.2469 (15)
C1—H1C	0.9800	C6—N2	1.3877 (16)
C2—N1	1.4818 (15)	C6—C7	1.4350 (17)
C2—H2A	0.9900	C7—C9	1.3979 (17)
C2—H2B	0.9900	C7—C8	1.4457 (17)
C3—N1	1.3746 (16)	C8—O1	1.2184 (16)
C3—N2	1.3887 (15)	C8—N1	1.4188 (16)
C3—S1	1.6588 (12)	C9—O3	1.3089 (15)
C4—N2	1.4849 (15)	C9—C10	1.4847 (18)
C4—C5	1.518 (2)	C10—H10A	0.9800
C4—H4A	0.9900	C10—H10B	0.9800
C4—H4B	0.9900	C10—H10C	0.9800
C5—H5A	0.9800	O3—H3	0.8400
C2—C1—H1A	109.5	H5B—C5—H5C	109.5
C2—C1—H1B	109.5	O2—C6—N2	119.10 (11)
H1A—C1—H1B	109.5	O2—C6—C7	122.41 (11)
C2—C1—H1C	109.5	N2—C6—C7	118.49 (11)
H1A—C1—H1C	109.5	C9—C7—C6	118.59 (11)
H1B—C1—H1C	109.5	C9—C7—C8	121.36 (11)
N1—C2—C1	111.45 (10)	C6—C7—C8	119.99 (11)
N1—C2—H2A	109.3	O1—C8—N1	118.83 (11)
C1—C2—H2A	109.3	O1—C8—C7	125.41 (12)
N1—C2—H2B	109.3	N1—C8—C7	115.75 (11)
C1—C2—H2B	109.3	O3—C9—C7	120.68 (12)
H2A—C2—H2B	108.0	O3—C9—C10	113.72 (11)
N1—C3—N2	117.05 (10)	C7—C9—C10	125.59 (12)
N1—C3—S1	121.94 (9)	C9—C10—H10A	109.5
N2—C3—S1	121.01 (9)	C9—C10—H10B	109.5
N2—C4—C5	111.49 (11)	H10A—C10—H10B	109.5
N2—C4—H4A	109.3	C9—C10—H10C	109.5
C5—C4—H4A	109.3	H10A—C10—H10C	109.5
N2—C4—H4B	109.3	H10B—C10—H10C	109.5
C5—C4—H4B	109.3	C3—N1—C8	124.98 (10)
H4A—C4—H4B	108.0	C3—N1—C2	119.30 (10)
C4—C5—H5A	109.5	C8—N1—C2	115.70 (10)
C4—C5—H5B	109.5	C6—N2—C3	123.53 (10)
H5A—C5—H5B	109.5	C6—N2—C4	117.14 (10)
C4—C5—H5C	109.5	C3—N2—C4	119.33 (10)
H5A—C5—H5C	109.5	C9—O3—H3	109.5
O2—C6—C7—C9	−5.16 (18)	O1—C8—N1—C3	176.16 (12)
N2—C6—C7—C9	174.28 (11)	C7—C8—N1—C3	−3.50 (17)
O2—C6—C7—C8	177.67 (11)	O1—C8—N1—C2	−5.83 (17)
N2—C6—C7—C8	−2.89 (17)	C7—C8—N1—C2	174.51 (10)
C9—C7—C8—O1	8.3 (2)	C1—C2—N1—C3	84.75 (14)
C6—C7—C8—O1	−174.57 (12)	C1—C2—N1—C8	−93.38 (13)
C9—C7—C8—N1	−172.03 (11)	O2—C6—N2—C3	178.14 (11)
C6—C7—C8—N1	5.06 (17)	C7—C6—N2—C3	−1.32 (17)
C6—C7—C9—O3	2.29 (18)	O2—C6—N2—C4	−1.88 (17)
C8—C7—C9—O3	179.42 (11)	C7—C6—N2—C4	178.66 (11)
C6—C7—C9—C10	−177.00 (12)	N1—C3—N2—C6	2.99 (17)
C8—C7—C9—C10	0.13 (19)	S1—C3—N2—C6	−177.18 (9)
N2—C3—N1—C8	−0.42 (17)	N1—C3—N2—C4	−176.99 (10)
S1—C3—N1—C8	179.74 (9)	S1—C3—N2—C4	2.84 (15)
N2—C3—N1—C2	−178.36 (10)	C5—C4—N2—C6	−98.68 (13)
S1—C3—N1—C2	1.80 (15)	C5—C4—N2—C3	81.30 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···S1	0.98	2.88	3.4223 (15)	116
C10—H10A···S1^i	0.98	2.88	3.8316 (14)	163
O3—H3···O2	0.84	1.71	2.4756 (13)	150
O3—H3···O2^ii	0.84	2.47	3.0073 (13)	122

Symmetry codes: (i) x−1/2, −y+3/2, z−1/2; (ii) −x, −y+2, −z+1.

1,3-Diethyl-5-propionyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (A02)

Crystal data

C11H16N2O3S	F(000) = 272
Mr = 256.32	Dx = 1.409 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 4.9140 (1) Å	Cell parameters from 7194 reflections
b = 12.9450 (3) Å	θ = 2.7–27.5°
c = 9.7630 (3) Å	µ = 0.27 mm^−1
β = 103.474 (1)°	T = 100 K
V = 603.95 (3) Å^3	Block, colourless
Z = 2	0.19 × 0.14 × 0.07 mm

Data collection

Bruker APEXII CCD diffractometer	8623 independent reflections
Radiation source: sealed tube	8469 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −6→6
Tmin = 0.940, Tmax = 0.991	k = −16→16
8623 measured reflections	l = −12→12

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.027	w = 1/[σ^2(Fo^2) + (0.0441P)^2 + 0.0526P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.070	(Δ/σ)max < 0.001
S = 1.09	Δρmax = 0.21 e Å^−3
8623 reflections	Δρmin = −0.26 e Å^−3
158 parameters	Absolute structure: Flack x determined using 1252 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraint	Absolute structure parameter: 0.034 (16)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.3177 (3)	0.72567 (12)	0.49804 (17)	0.0214 (4)
O2	0.1016 (3)	0.37732 (11)	0.38393 (16)	0.0186 (3)
C5	0.1988 (4)	0.54922 (16)	0.4577 (2)	0.0146 (4)
N2	0.4821 (4)	0.64360 (14)	0.32802 (19)	0.0155 (4)
C1	−0.1348 (5)	0.58442 (19)	0.7760 (3)	0.0281 (6)
H1A	−0.030796	0.526690	0.828470	0.042*
H1B	−0.324936	0.561794	0.730933	0.042*
H1C	−0.143850	0.641443	0.840824	0.042*
C2	0.0123 (4)	0.62058 (18)	0.6641 (2)	0.0191 (5)
H2A	−0.093981	0.679108	0.612254	0.023*
H2B	0.200516	0.646446	0.711133	0.023*
C3	0.0435 (4)	0.53884 (15)	0.5607 (2)	0.0159 (4)
C4	0.2242 (4)	0.46125 (17)	0.3735 (2)	0.0155 (4)
N1	0.3909 (3)	0.46756 (14)	0.27790 (19)	0.0157 (4)
C6	0.4312 (4)	0.37043 (16)	0.2038 (2)	0.0176 (5)
H6A	0.434322	0.311261	0.268416	0.021*
H6B	0.614315	0.372912	0.178006	0.021*
C7	0.2017 (4)	0.35365 (19)	0.0718 (2)	0.0234 (5)
H7A	0.020823	0.347983	0.097378	0.035*
H7B	0.238772	0.289922	0.025153	0.035*
H7C	0.197113	0.412224	0.007745	0.035*
C8	0.5062 (4)	0.55963 (19)	0.2455 (2)	0.0160 (4)
C9	0.3308 (4)	0.64530 (17)	0.4348 (2)	0.0158 (4)
O3	−0.0832 (3)	0.45221 (11)	0.57302 (17)	0.0198 (3)
H3	−0.053435	0.409823	0.513011	0.030*
C11	0.6030 (4)	0.74399 (18)	0.2997 (2)	0.0198 (5)
H11A	0.771894	0.731567	0.263124	0.024*
H11B	0.660559	0.783241	0.388804	0.024*
C12	0.3955 (5)	0.80712 (19)	0.1941 (3)	0.0261 (5)
H12A	0.334132	0.767587	0.106781	0.039*
H12B	0.484358	0.871449	0.174372	0.039*
H12C	0.233420	0.823310	0.232739	0.039*
S1	0.66844 (10)	0.56606 (5)	0.11383 (6)	0.02182 (15)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0278 (8)	0.0164 (8)	0.0221 (8)	−0.0033 (6)	0.0104 (7)	−0.0031 (6)
O2	0.0214 (7)	0.0139 (7)	0.0221 (8)	−0.0018 (6)	0.0085 (6)	0.0006 (6)
C5	0.0156 (8)	0.0131 (12)	0.0152 (9)	0.0000 (8)	0.0036 (7)	0.0004 (8)
N2	0.0164 (8)	0.0136 (9)	0.0172 (10)	−0.0022 (7)	0.0053 (7)	−0.0004 (7)
C1	0.0436 (13)	0.0212 (14)	0.0252 (12)	0.0035 (10)	0.0193 (11)	0.0023 (9)
C2	0.0241 (10)	0.0177 (11)	0.0176 (11)	0.0017 (9)	0.0090 (9)	−0.0006 (8)
C3	0.0150 (9)	0.0154 (11)	0.0166 (10)	0.0025 (8)	0.0022 (8)	0.0027 (8)
C4	0.0133 (9)	0.0162 (10)	0.0164 (10)	0.0025 (8)	0.0020 (8)	0.0035 (8)
N1	0.0180 (9)	0.0138 (9)	0.0161 (9)	0.0020 (7)	0.0056 (7)	−0.0005 (7)
C6	0.0198 (10)	0.0127 (11)	0.0217 (11)	0.0033 (8)	0.0080 (9)	−0.0015 (8)
C7	0.0252 (11)	0.0235 (13)	0.0217 (12)	0.0033 (9)	0.0056 (9)	−0.0043 (10)
C8	0.0135 (8)	0.0163 (10)	0.0178 (10)	0.0018 (9)	0.0027 (8)	0.0007 (9)
C9	0.0150 (9)	0.0166 (11)	0.0152 (11)	0.0012 (8)	0.0021 (8)	0.0015 (9)
O3	0.0249 (8)	0.0143 (8)	0.0234 (9)	−0.0015 (6)	0.0122 (7)	−0.0008 (6)
C11	0.0228 (10)	0.0165 (11)	0.0218 (12)	−0.0057 (8)	0.0089 (9)	0.0003 (9)
C12	0.0334 (12)	0.0172 (12)	0.0320 (14)	0.0044 (10)	0.0163 (11)	0.0074 (10)
S1	0.0268 (3)	0.0199 (3)	0.0233 (3)	0.0010 (2)	0.0151 (2)	0.0016 (2)

Geometric parameters (Å, º)

O1—C9	1.219 (3)	N1—C8	1.388 (3)
O2—C4	1.258 (3)	N1—C6	1.487 (3)
C5—C3	1.403 (3)	C6—C7	1.517 (3)
C5—C4	1.427 (3)	C6—H6A	0.9900
C5—C9	1.444 (3)	C6—H6B	0.9900
N2—C8	1.375 (3)	C7—H7A	0.9800
N2—C9	1.415 (3)	C7—H7B	0.9800
N2—C11	1.481 (3)	C7—H7C	0.9800
C1—C2	1.518 (3)	C8—S1	1.665 (2)
C1—H1A	0.9800	O3—H3	0.8400
C1—H1B	0.9800	C11—C12	1.510 (3)
C1—H1C	0.9800	C11—H11A	0.9900
C2—C3	1.495 (3)	C11—H11B	0.9900
C2—H2A	0.9900	C12—H12A	0.9800
C2—H2B	0.9900	C12—H12B	0.9800
C3—O3	1.302 (2)	C12—H12C	0.9800
C4—N1	1.380 (3)
C3—C5—C4	118.13 (18)	C7—C6—H6A	109.2
C3—C5—C9	122.15 (18)	N1—C6—H6B	109.2
C4—C5—C9	119.72 (18)	C7—C6—H6B	109.2
C8—N2—C9	125.18 (18)	H6A—C6—H6B	107.9
C8—N2—C11	119.42 (17)	C6—C7—H7A	109.5
C9—N2—C11	115.24 (18)	C6—C7—H7B	109.5
C2—C1—H1A	109.5	H7A—C7—H7B	109.5
C2—C1—H1B	109.5	C6—C7—H7C	109.5
H1A—C1—H1B	109.5	H7A—C7—H7C	109.5
C2—C1—H1C	109.5	H7B—C7—H7C	109.5
H1A—C1—H1C	109.5	N2—C8—N1	116.74 (17)
H1B—C1—H1C	109.5	N2—C8—S1	122.36 (17)
C3—C2—C1	114.14 (19)	N1—C8—S1	120.90 (17)
C3—C2—H2A	108.7	O1—C9—N2	119.02 (19)
C1—C2—H2A	108.7	O1—C9—C5	125.34 (19)
C3—C2—H2B	108.7	N2—C9—C5	115.63 (18)
C1—C2—H2B	108.7	C3—O3—H3	109.5
H2A—C2—H2B	107.6	N2—C11—C12	111.45 (17)
O3—C3—C5	120.04 (19)	N2—C11—H11A	109.3
O3—C3—C2	114.87 (18)	C12—C11—H11A	109.3
C5—C3—C2	125.08 (18)	N2—C11—H11B	109.3
O2—C4—N1	118.5 (2)	C12—C11—H11B	109.3
O2—C4—C5	122.33 (19)	H11A—C11—H11B	108.0
N1—C4—C5	119.19 (18)	C11—C12—H12A	109.5
C4—N1—C8	122.91 (18)	C11—C12—H12B	109.5
C4—N1—C6	116.51 (17)	H12A—C12—H12B	109.5
C8—N1—C6	120.51 (17)	C11—C12—H12C	109.5
N1—C6—C7	112.16 (17)	H12A—C12—H12C	109.5
N1—C6—H6A	109.2	H12B—C12—H12C	109.5
C4—C5—C3—O3	−3.1 (3)	C11—N2—C8—N1	179.47 (16)
C9—C5—C3—O3	176.66 (18)	C9—N2—C8—S1	175.37 (14)
C4—C5—C3—C2	175.57 (18)	C11—N2—C8—S1	0.2 (3)
C9—C5—C3—C2	−4.6 (3)	C4—N1—C8—N2	9.3 (3)
C1—C2—C3—O3	6.4 (3)	C6—N1—C8—N2	−173.90 (16)
C1—C2—C3—C5	−172.34 (19)	C4—N1—C8—S1	−171.45 (15)
C3—C5—C4—O2	3.6 (3)	C6—N1—C8—S1	5.3 (3)
C9—C5—C4—O2	−176.22 (18)	C8—N2—C9—O1	−177.70 (19)
C3—C5—C4—N1	−175.80 (18)	C11—N2—C9—O1	−2.4 (3)
C9—C5—C4—N1	4.4 (3)	C8—N2—C9—C5	1.3 (3)
O2—C4—N1—C8	171.61 (18)	C11—N2—C9—C5	176.63 (16)
C5—C4—N1—C8	−9.0 (3)	C3—C5—C9—O1	−1.6 (3)
O2—C4—N1—C6	−5.3 (3)	C4—C5—C9—O1	178.24 (19)
C5—C4—N1—C6	174.09 (16)	C3—C5—C9—N2	179.51 (18)
C4—N1—C6—C7	87.0 (2)	C4—C5—C9—N2	−0.7 (3)
C8—N1—C6—C7	−90.0 (2)	C8—N2—C11—C12	88.9 (2)
C9—N2—C8—N1	−5.4 (3)	C9—N2—C11—C12	−86.7 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O2^i	0.99	2.57	3.385 (3)	140
C6—H6A···O1^ii	0.99	2.57	3.440 (3)	146
C11—H11B···O2^iii	0.99	2.56	3.541 (3)	170
O3—H3···O2	0.84	1.67	2.440 (2)	151

Symmetry codes: (i) −x, y+1/2, −z+1; (ii) −x+1, y−1/2, −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)

Crystal data

C18H29N3O5S	Dx = 1.354 Mg m^−3
Mr = 399.50	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 9709 reflections
a = 8.3816 (12) Å	θ = 2.3–27.6°
b = 9.6258 (14) Å	µ = 0.20 mm^−1
c = 24.297 (3) Å	T = 100 K
V = 1960.3 (5) Å^3	Block, colourless
Z = 4	0.33 × 0.25 × 0.21 mm
F(000) = 856

Data collection

Bruker APEXII CCD diffractometer	15360 independent reflections
Radiation source: sealed tube	14556 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 27.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −10→8
Tmin = 0.925, Tmax = 0.968	k = −12→12
15360 measured reflections	l = −31→28

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.028	w = 1/[σ^2(Fo^2) + (0.0272P)^2 + 0.5031P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.070	(Δ/σ)max = 0.001
S = 1.04	Δρmax = 0.47 e Å^−3
15360 reflections	Δρmin = −0.30 e Å^−3
264 parameters	Absolute structure: Flack x determined using 1707 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
5 restraints	Absolute structure parameter: 0.001 (2)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.2383 (3)	0.8543 (3)	0.93914 (10)	0.0272 (6)
H1A	0.176111	0.780871	0.921212	0.041*
H1B	0.165661	0.921401	0.956221	0.041*
H1C	0.306906	0.813187	0.967456	0.041*
C2	0.3395 (3)	0.9267 (2)	0.89713 (9)	0.0179 (5)
H2A	0.269559	0.974270	0.870259	0.021*
H2B	0.405263	0.998194	0.915642	0.021*
C8	0.3789 (3)	0.7723 (2)	0.81999 (9)	0.0147 (5)
C9	0.4471 (3)	0.6340 (2)	0.73724 (9)	0.0157 (5)
C10	0.2971 (2)	0.6640 (2)	0.70544 (9)	0.0154 (5)
H10	0.244444	0.748873	0.720766	0.018*
C15	0.6228 (3)	0.8459 (2)	0.56077 (10)	0.0204 (5)
C14	0.4478 (3)	0.7825 (2)	0.63569 (9)	0.0170 (5)
C17	0.6270 (3)	0.7970 (3)	0.50255 (10)	0.0302 (6)
H17A	0.528464	0.824740	0.483854	0.045*
H17B	0.636686	0.695525	0.501853	0.045*
H17C	0.718745	0.838476	0.483697	0.045*
C3	0.5935 (3)	0.8077 (2)	0.88664 (9)	0.0172 (5)
C6	0.6383 (3)	0.6611 (2)	0.80864 (9)	0.0170 (5)
N2	0.6884 (2)	0.72189 (19)	0.85597 (8)	0.0165 (4)
C4	0.8554 (3)	0.6961 (3)	0.87195 (10)	0.0249 (6)
H4A	0.894512	0.774890	0.894399	0.030*
H4B	0.922293	0.690459	0.838428	0.030*
C5	0.8721 (3)	0.5651 (3)	0.90395 (12)	0.0366 (7)
H5A	0.839680	0.486213	0.881032	0.055*
H5B	0.804131	0.569445	0.936715	0.055*
H5C	0.983622	0.553283	0.915187	0.055*
C11	0.1811 (3)	0.5412 (2)	0.70810 (10)	0.0190 (5)
H11	0.228993	0.463815	0.686188	0.023*
C12	0.1553 (3)	0.4880 (3)	0.76531 (10)	0.0252 (6)
H12A	0.079967	0.410248	0.764402	0.038*
H12B	0.111986	0.562602	0.788342	0.038*
H12C	0.257240	0.456467	0.780629	0.038*
C13	0.0255 (3)	0.5789 (3)	0.68128 (11)	0.0294 (6)
H13A	0.045063	0.607953	0.643222	0.044*
H13B	−0.024473	0.655239	0.701633	0.044*
H13C	−0.045504	0.498008	0.681496	0.044*
C18	0.5949 (3)	0.9999 (2)	0.56391 (12)	0.0336 (7)
H18A	0.676742	1.048385	0.542446	0.050*
H18B	0.600427	1.030111	0.602386	0.050*
H18C	0.489215	1.021770	0.548949	0.050*
C16	0.7711 (3)	0.8032 (3)	0.59051 (11)	0.0279 (6)
H16A	0.782223	0.701934	0.588917	0.042*
H16B	0.764416	0.832903	0.629021	0.042*
H16C	0.863932	0.846781	0.573080	0.042*
N1	0.4442 (2)	0.83019 (18)	0.86787 (7)	0.0140 (4)
C7	0.4840 (3)	0.6877 (2)	0.78880 (9)	0.0139 (5)
N3	0.3372 (2)	0.6871 (2)	0.64868 (8)	0.0170 (4)
O1	0.24103 (17)	0.79625 (16)	0.80922 (6)	0.0184 (4)
O2	0.73574 (18)	0.58447 (17)	0.78407 (7)	0.0210 (4)
O3	0.54486 (19)	0.55537 (17)	0.71284 (7)	0.0203 (4)
O4	0.50057 (18)	0.86552 (17)	0.66745 (6)	0.0223 (4)
O5	0.48618 (18)	0.77041 (17)	0.58289 (6)	0.0192 (4)
S1	0.66106 (8)	0.88046 (6)	0.94304 (3)	0.02442 (16)
H3	0.327 (3)	0.624 (2)	0.6266 (9)	0.027 (7)*
H2	0.695 (3)	0.563 (5)	0.7528 (9)	0.03 (2)*	0.50 (7)
H3A	0.627 (3)	0.549 (5)	0.7338 (10)	0.03 (2)*	0.50 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0309 (14)	0.0277 (13)	0.0229 (13)	0.0047 (12)	0.0080 (12)	−0.0008 (12)
C2	0.0224 (12)	0.0172 (11)	0.0141 (12)	0.0049 (11)	0.0003 (10)	−0.0028 (9)
C8	0.0179 (12)	0.0122 (10)	0.0141 (11)	−0.0019 (10)	0.0012 (10)	0.0018 (9)
C9	0.0157 (12)	0.0134 (11)	0.0179 (12)	−0.0023 (11)	0.0042 (9)	0.0013 (10)
C10	0.0150 (12)	0.0169 (12)	0.0142 (11)	−0.0007 (9)	−0.0004 (9)	−0.0017 (10)
C15	0.0230 (12)	0.0185 (11)	0.0196 (12)	−0.0056 (10)	0.0075 (11)	0.0014 (10)
C14	0.0179 (12)	0.0176 (11)	0.0155 (12)	0.0025 (11)	−0.0008 (10)	0.0002 (10)
C17	0.0366 (16)	0.0328 (15)	0.0211 (13)	−0.0102 (13)	0.0074 (12)	−0.0023 (12)
C3	0.0217 (13)	0.0130 (11)	0.0168 (12)	−0.0013 (10)	−0.0012 (10)	0.0031 (10)
C6	0.0191 (12)	0.0148 (11)	0.0172 (12)	−0.0009 (10)	0.0021 (10)	0.0014 (9)
N2	0.0139 (10)	0.0171 (9)	0.0186 (10)	0.0012 (8)	−0.0026 (8)	−0.0002 (9)
C4	0.0152 (12)	0.0308 (14)	0.0286 (14)	0.0040 (12)	−0.0070 (11)	−0.0051 (12)
C5	0.0322 (15)	0.0345 (15)	0.0430 (18)	0.0137 (13)	−0.0141 (14)	−0.0005 (14)
C11	0.0184 (12)	0.0192 (12)	0.0192 (13)	−0.0032 (10)	0.0012 (10)	−0.0004 (10)
C12	0.0254 (13)	0.0251 (13)	0.0251 (14)	−0.0051 (12)	0.0032 (11)	0.0050 (11)
C13	0.0205 (13)	0.0364 (15)	0.0314 (15)	−0.0089 (12)	−0.0048 (11)	0.0080 (13)
C18	0.0482 (17)	0.0222 (13)	0.0304 (16)	−0.0015 (13)	0.0112 (14)	0.0046 (12)
C16	0.0215 (13)	0.0319 (15)	0.0303 (15)	−0.0054 (12)	0.0054 (11)	−0.0049 (13)
N1	0.0149 (10)	0.0143 (9)	0.0128 (9)	0.0016 (8)	−0.0001 (8)	−0.0001 (8)
C7	0.0128 (11)	0.0143 (11)	0.0145 (11)	−0.0008 (9)	0.0008 (9)	0.0017 (9)
N3	0.0203 (10)	0.0178 (10)	0.0129 (10)	−0.0044 (9)	−0.0010 (9)	−0.0026 (9)
O1	0.0139 (8)	0.0234 (9)	0.0180 (9)	0.0036 (7)	−0.0011 (7)	−0.0028 (7)
O2	0.0167 (8)	0.0258 (10)	0.0205 (10)	0.0058 (7)	0.0008 (8)	−0.0050 (8)
O3	0.0172 (9)	0.0247 (9)	0.0190 (9)	0.0048 (8)	−0.0003 (8)	−0.0065 (7)
O4	0.0264 (9)	0.0207 (8)	0.0199 (9)	−0.0064 (8)	0.0019 (7)	−0.0045 (8)
O5	0.0211 (9)	0.0230 (9)	0.0134 (8)	−0.0070 (7)	0.0028 (7)	−0.0002 (7)
S1	0.0295 (3)	0.0236 (3)	0.0201 (3)	0.0030 (3)	−0.0098 (3)	−0.0048 (3)

Geometric parameters (Å, º)

C1—C2	1.499 (3)	C6—O2	1.252 (3)
C1—H1A	0.9800	C6—N2	1.357 (3)
C1—H1B	0.9800	C6—C7	1.404 (3)
C1—H1C	0.9800	N2—C4	1.474 (3)
C2—N1	1.462 (3)	C4—C5	1.488 (3)
C2—H2A	0.9900	C4—H4A	0.9900
C2—H2B	0.9900	C4—H4B	0.9900
C8—O1	1.207 (3)	C5—H5A	0.9800
C8—N1	1.401 (3)	C5—H5B	0.9800
C8—C7	1.419 (3)	C5—H5C	0.9800
C9—O3	1.263 (3)	C11—C12	1.497 (3)
C9—C7	1.390 (3)	C11—C13	1.502 (3)
C9—C10	1.504 (3)	C11—H11	1.0000
C10—N3	1.437 (3)	C12—H12A	0.9800
C10—C11	1.532 (3)	C12—H12B	0.9800
C10—H10	1.0000	C12—H12C	0.9800
C15—O5	1.459 (3)	C13—H13A	0.9800
C15—C17	1.491 (3)	C13—H13B	0.9800
C15—C16	1.496 (3)	C13—H13C	0.9800
C15—C18	1.503 (3)	C18—H18A	0.9800
C14—O4	1.196 (3)	C18—H18B	0.9800
C14—O5	1.328 (3)	C18—H18C	0.9800
C14—N3	1.343 (3)	C16—H16A	0.9800
C17—H17A	0.9800	C16—H16B	0.9800
C17—H17B	0.9800	C16—H16C	0.9800
C17—H17C	0.9800	N3—H3	0.816 (18)
C3—N1	1.349 (3)	O2—H2	0.860 (3)
C3—N2	1.368 (3)	O3—H3A	0.860 (3)
C3—S1	1.640 (2)
C2—C1—H1A	109.5	N2—C4—H4B	109.3
C2—C1—H1B	109.5	C5—C4—H4B	109.3
H1A—C1—H1B	109.5	H4A—C4—H4B	107.9
C2—C1—H1C	109.5	C4—C5—H5A	109.5
H1A—C1—H1C	109.5	C4—C5—H5B	109.5
H1B—C1—H1C	109.5	H5A—C5—H5B	109.5
N1—C2—C1	112.05 (19)	C4—C5—H5C	109.5
N1—C2—H2A	109.2	H5A—C5—H5C	109.5
C1—C2—H2A	109.2	H5B—C5—H5C	109.5
N1—C2—H2B	109.2	C12—C11—C13	111.1 (2)
C1—C2—H2B	109.2	C12—C11—C10	113.2 (2)
H2A—C2—H2B	107.9	C13—C11—C10	110.26 (19)
O1—C8—N1	118.5 (2)	C12—C11—H11	107.3
O1—C8—C7	126.0 (2)	C13—C11—H11	107.3
N1—C8—C7	115.43 (19)	C10—C11—H11	107.3
O3—C9—C7	120.1 (2)	C11—C12—H12A	109.5
O3—C9—C10	114.61 (19)	C11—C12—H12B	109.5
C7—C9—C10	125.3 (2)	H12A—C12—H12B	109.5
N3—C10—C9	109.09 (18)	C11—C12—H12C	109.5
N3—C10—C11	107.94 (19)	H12A—C12—H12C	109.5
C9—C10—C11	111.15 (18)	H12B—C12—H12C	109.5
N3—C10—H10	109.5	C11—C13—H13A	109.5
C9—C10—H10	109.5	C11—C13—H13B	109.5
C11—C10—H10	109.5	H13A—C13—H13B	109.5
O5—C15—C17	102.17 (18)	C11—C13—H13C	109.5
O5—C15—C16	109.71 (18)	H13A—C13—H13C	109.5
C17—C15—C16	110.6 (2)	H13B—C13—H13C	109.5
O5—C15—C18	110.53 (19)	C15—C18—H18A	109.5
C17—C15—C18	111.3 (2)	C15—C18—H18B	109.5
C16—C15—C18	112.1 (2)	H18A—C18—H18B	109.5
O4—C14—O5	126.3 (2)	C15—C18—H18C	109.5
O4—C14—N3	124.1 (2)	H18A—C18—H18C	109.5
O5—C14—N3	109.6 (2)	H18B—C18—H18C	109.5
C15—C17—H17A	109.5	C15—C16—H16A	109.5
C15—C17—H17B	109.5	C15—C16—H16B	109.5
H17A—C17—H17B	109.5	H16A—C16—H16B	109.5
C15—C17—H17C	109.5	C15—C16—H16C	109.5
H17A—C17—H17C	109.5	H16A—C16—H16C	109.5
H17B—C17—H17C	109.5	H16B—C16—H16C	109.5
N1—C3—N2	116.87 (19)	C3—N1—C8	125.37 (18)
N1—C3—S1	122.31 (17)	C3—N1—C2	119.59 (19)
N2—C3—S1	120.81 (17)	C8—N1—C2	114.98 (17)
O2—C6—N2	117.1 (2)	C9—C7—C6	116.5 (2)
O2—C6—C7	123.0 (2)	C9—C7—C8	123.8 (2)
N2—C6—C7	119.8 (2)	C6—C7—C8	119.6 (2)
C6—N2—C3	122.84 (19)	C14—N3—C10	119.53 (19)
C6—N2—C4	116.39 (19)	C14—N3—H3	115.5 (18)
C3—N2—C4	120.72 (19)	C10—N3—H3	119.3 (18)
N2—C4—C5	111.7 (2)	C6—O2—H2	107.6 (4)
N2—C4—H4A	109.3	C9—O3—H3A	106.6 (4)
C5—C4—H4A	109.3	C14—O5—C15	120.17 (18)
O3—C9—C10—N3	−41.3 (3)	C7—C8—N1—C2	174.93 (18)
C7—C9—C10—N3	137.3 (2)	C1—C2—N1—C3	−92.5 (2)
O3—C9—C10—C11	77.6 (2)	C1—C2—N1—C8	90.1 (2)
C7—C9—C10—C11	−103.8 (3)	O3—C9—C7—C6	6.1 (3)
O2—C6—N2—C3	−180.0 (2)	C10—C9—C7—C6	−172.4 (2)
C7—C6—N2—C3	1.2 (3)	O3—C9—C7—C8	−177.47 (19)
O2—C6—N2—C4	2.8 (3)	C10—C9—C7—C8	4.0 (3)
C7—C6—N2—C4	−176.0 (2)	O2—C6—C7—C9	−5.4 (3)
N1—C3—N2—C6	0.2 (3)	N2—C6—C7—C9	173.3 (2)
S1—C3—N2—C6	−179.03 (17)	O2—C6—C7—C8	178.0 (2)
N1—C3—N2—C4	177.34 (19)	N2—C6—C7—C8	−3.3 (3)
S1—C3—N2—C4	−1.9 (3)	O1—C8—C7—C9	8.4 (4)
C6—N2—C4—C5	−86.0 (3)	N1—C8—C7—C9	−172.6 (2)
C3—N2—C4—C5	96.7 (3)	O1—C8—C7—C6	−175.3 (2)
N3—C10—C11—C12	168.4 (2)	N1—C8—C7—C6	3.7 (3)
C9—C10—C11—C12	48.8 (3)	O4—C14—N3—C10	−11.4 (3)
N3—C10—C11—C13	−66.4 (2)	O5—C14—N3—C10	169.31 (19)
C9—C10—C11—C13	174.0 (2)	C9—C10—N3—C14	−53.7 (3)
N2—C3—N1—C8	0.4 (3)	C11—C10—N3—C14	−174.61 (19)
S1—C3—N1—C8	179.63 (17)	O4—C14—O5—C15	11.1 (3)
N2—C3—N1—C2	−176.76 (18)	N3—C14—O5—C15	−169.58 (18)
S1—C3—N1—C2	2.5 (3)	C17—C15—O5—C14	177.0 (2)
O1—C8—N1—C3	176.7 (2)	C16—C15—O5—C14	59.7 (3)
C7—C8—N1—C3	−2.3 (3)	C18—C15—O5—C14	−64.4 (3)
O1—C8—N1—C2	−6.0 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1	1.00	2.20	2.863 (3)	123
C11—H11···N2^i	1.00	2.64	3.615 (3)	166
C18—H18A···S1^ii	0.98	2.86	3.760 (3)	154
C18—H18B···O4	0.98	2.39	2.937 (3)	115
C16—H16B···O4	0.98	2.42	3.000 (3)	117
N3—H3···S1^i	0.82 (2)	2.89 (2)	3.698 (2)	170 (2)
O2—H2···O3	0.86 (1)	1.59 (1)	2.374 (2)	150 (1)
O3—H3A···O2	0.86 (1)	1.56 (1)	2.374 (2)	156 (1)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) −x+3/2, −y+2, z−1/2.

1,3-Diethyl-4,6-dioxo-2-thioxo-<i.N-(p-tolyl)hexahydropyrimidine-5-carbothioamide (A13)

Crystal data

C16H19N3O2S2	F(000) = 736
Mr = 349.46	Dx = 1.467 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.8156 (2) Å	Cell parameters from 9954 reflections
b = 21.7395 (7) Å	θ = 2.3–28.6°
c = 15.1912 (5) Å	µ = 0.35 mm^−1
β = 95.656 (1)°	T = 100 K
V = 1582.61 (10) Å^3	Rod, yellow
Z = 4	0.19 × 0.12 × 0.11 mm

Data collection

Bruker APEXII CCD diffractometer	4036 independent reflections
Radiation source: sealed tube	3430 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 28.7°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −6→6
Tmin = 0.925, Tmax = 0.976	k = −28→29
25387 measured reflections	l = −16→20

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.031	H-atom parameters constrained
wR(F^2) = 0.078	w = 1/[σ^2(Fo^2) + (0.0319P)^2 + 0.9919P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.003
4036 reflections	Δρmax = 0.38 e Å^−3
212 parameters	Δρmin = −0.25 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6364 (3)	0.05024 (7)	1.11011 (9)	0.0200 (3)
H1A	0.444617	0.059313	1.122381	0.030*
H1B	0.738110	0.031661	1.162536	0.030*
H1C	0.633537	0.021547	1.060273	0.030*
C2	0.7801 (3)	0.10933 (6)	1.08713 (9)	0.0165 (3)
H2B	0.802275	0.136248	1.139925	0.020*
H2C	0.968596	0.099599	1.070263	0.020*
C3	0.4240 (3)	0.18473 (6)	1.03472 (8)	0.0130 (2)
C4	0.2647 (3)	0.21854 (6)	0.96914 (8)	0.0122 (2)
C5	0.0575 (3)	0.26444 (6)	0.99080 (8)	0.0124 (2)
C6	−0.2913 (3)	0.33867 (6)	0.91476 (8)	0.0132 (3)
C7	−0.4266 (3)	0.34618 (6)	0.82949 (9)	0.0153 (3)
H7	−0.379058	0.320332	0.782841	0.018*
C8	−0.6294 (3)	0.39103 (6)	0.81270 (9)	0.0166 (3)
H8	−0.719285	0.395317	0.754494	0.020*
C9	−0.7045 (3)	0.43003 (6)	0.87935 (9)	0.0159 (3)
C10	−0.9212 (3)	0.47956 (7)	0.86014 (10)	0.0200 (3)
H10A	−1.107692	0.461102	0.855538	0.030*
H10B	−0.891626	0.499911	0.804258	0.030*
H10C	−0.904996	0.509862	0.908134	0.030*
C11	0.6700 (3)	0.12958 (6)	0.92701 (9)	0.0132 (2)
C12	0.5668 (3)	0.15332 (6)	0.76841 (8)	0.0148 (3)
H12A	0.767628	0.145225	0.764691	0.018*
H12B	0.516924	0.191291	0.734493	0.018*
C13	0.3974 (3)	0.09994 (7)	0.72690 (9)	0.0184 (3)
H13A	0.453484	0.061833	0.758223	0.028*
H13B	0.431028	0.096098	0.664552	0.028*
H13C	0.198559	0.107472	0.731147	0.028*
C14	0.3072 (3)	0.20499 (6)	0.87829 (8)	0.0124 (2)
C15	−0.5709 (3)	0.42136 (6)	0.96368 (9)	0.0187 (3)
H15	−0.621330	0.446804	1.010404	0.022*
C16	−0.3657 (3)	0.37673 (6)	0.98239 (9)	0.0183 (3)
H16	−0.277263	0.372309	1.040768	0.022*
N1	0.6200 (2)	0.14275 (5)	1.01321 (7)	0.0132 (2)
N2	−0.0813 (2)	0.29283 (5)	0.92183 (7)	0.0134 (2)
H2A	−0.032193	0.280534	0.870382	0.016*
N3	0.5180 (2)	0.16309 (5)	0.86255 (7)	0.0125 (2)
O1	0.1706 (2)	0.22802 (4)	0.81289 (6)	0.0156 (2)
O2	0.4004 (2)	0.18827 (4)	1.11873 (6)	0.0158 (2)
H2	0.282227	0.215350	1.127983	0.024*
S1	0.90026 (7)	0.07630 (2)	0.90407 (2)	0.01698 (9)
S2	−0.00427 (8)	0.27972 (2)	1.09736 (2)	0.01633 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0230 (8)	0.0181 (7)	0.0185 (7)	0.0025 (6)	0.0010 (6)	0.0038 (5)
C2	0.0157 (7)	0.0187 (7)	0.0143 (6)	0.0026 (5)	−0.0029 (5)	0.0022 (5)
C3	0.0126 (6)	0.0126 (6)	0.0137 (6)	−0.0027 (5)	0.0009 (5)	0.0000 (5)
C4	0.0134 (6)	0.0123 (6)	0.0108 (5)	−0.0010 (5)	0.0011 (5)	−0.0007 (4)
C5	0.0133 (6)	0.0116 (6)	0.0125 (6)	−0.0027 (5)	0.0015 (5)	−0.0009 (4)
C6	0.0134 (6)	0.0121 (6)	0.0143 (6)	0.0003 (5)	0.0023 (5)	0.0002 (5)
C7	0.0170 (7)	0.0159 (6)	0.0129 (6)	−0.0007 (5)	0.0016 (5)	−0.0012 (5)
C8	0.0167 (7)	0.0172 (6)	0.0151 (6)	−0.0008 (5)	−0.0015 (5)	0.0009 (5)
C9	0.0133 (6)	0.0145 (6)	0.0201 (6)	−0.0016 (5)	0.0027 (5)	0.0025 (5)
C10	0.0165 (7)	0.0179 (7)	0.0252 (7)	0.0027 (5)	0.0008 (6)	0.0020 (5)
C11	0.0120 (6)	0.0121 (6)	0.0155 (6)	−0.0027 (5)	0.0018 (5)	0.0005 (5)
C12	0.0162 (7)	0.0174 (6)	0.0116 (6)	0.0011 (5)	0.0053 (5)	−0.0003 (5)
C13	0.0204 (7)	0.0205 (7)	0.0146 (6)	−0.0005 (5)	0.0034 (5)	−0.0048 (5)
C14	0.0123 (6)	0.0113 (6)	0.0134 (6)	−0.0024 (5)	0.0011 (5)	−0.0009 (4)
C15	0.0227 (7)	0.0169 (7)	0.0171 (6)	0.0048 (6)	0.0046 (5)	−0.0014 (5)
C16	0.0235 (7)	0.0183 (7)	0.0130 (6)	0.0042 (6)	0.0005 (5)	−0.0007 (5)
N1	0.0132 (6)	0.0134 (5)	0.0128 (5)	0.0002 (4)	−0.0004 (4)	0.0009 (4)
N2	0.0161 (6)	0.0138 (5)	0.0105 (5)	0.0025 (4)	0.0019 (4)	−0.0006 (4)
N3	0.0130 (6)	0.0133 (5)	0.0115 (5)	−0.0003 (4)	0.0023 (4)	−0.0005 (4)
O1	0.0188 (5)	0.0169 (5)	0.0109 (4)	0.0030 (4)	0.0004 (4)	0.0003 (3)
O2	0.0181 (5)	0.0188 (5)	0.0105 (4)	0.0032 (4)	0.0011 (4)	0.0006 (4)
S1	0.01535 (17)	0.01646 (17)	0.01953 (17)	0.00346 (12)	0.00381 (13)	0.00027 (12)
S2	0.02104 (18)	0.01790 (17)	0.01023 (15)	0.00360 (13)	0.00249 (12)	−0.00065 (12)

Geometric parameters (Å, º)

C1—C2	1.516 (2)	C9—C10	1.5078 (19)
C1—H1A	0.9800	C10—H10A	0.9800
C1—H1B	0.9800	C10—H10B	0.9800
C1—H1C	0.9800	C10—H10C	0.9800
C2—N1	1.4876 (16)	C11—N3	1.3726 (16)
C2—H2B	0.9900	C11—N1	1.3846 (17)
C2—H2C	0.9900	C11—S1	1.6639 (14)
C3—O2	1.2947 (16)	C12—N3	1.4874 (16)
C3—N1	1.3752 (17)	C12—C13	1.5192 (19)
C3—C4	1.4038 (17)	C12—H12A	0.9900
C4—C14	1.4453 (17)	C12—H12B	0.9900
C4—C5	1.4711 (18)	C13—H13A	0.9800
C5—N2	1.3370 (16)	C13—H13B	0.9800
C5—S2	1.7071 (13)	C13—H13C	0.9800
C6—C16	1.3931 (18)	C14—O1	1.2415 (16)
C6—C7	1.4011 (18)	C14—N3	1.4019 (17)
C6—N2	1.4164 (17)	C15—C16	1.3942 (19)
C7—C8	1.3855 (19)	C15—H15	0.9500
C7—H7	0.9500	C16—H16	0.9500
C8—C9	1.395 (2)	N2—H2A	0.8800
C8—H8	0.9500	O2—H2	0.8400
C9—C15	1.3885 (19)
C2—C1—H1A	109.5	H10A—C10—H10C	109.5
C2—C1—H1B	109.5	H10B—C10—H10C	109.5
H1A—C1—H1B	109.5	N3—C11—N1	115.75 (11)
C2—C1—H1C	109.5	N3—C11—S1	122.66 (10)
H1A—C1—H1C	109.5	N1—C11—S1	121.58 (10)
H1B—C1—H1C	109.5	N3—C12—C13	112.27 (11)
N1—C2—C1	111.91 (11)	N3—C12—H12A	109.2
N1—C2—H2B	109.2	C13—C12—H12A	109.2
C1—C2—H2B	109.2	N3—C12—H12B	109.2
N1—C2—H2C	109.2	C13—C12—H12B	109.2
C1—C2—H2C	109.2	H12A—C12—H12B	107.9
H2B—C2—H2C	107.9	C12—C13—H13A	109.5
O2—C3—N1	113.75 (11)	C12—C13—H13B	109.5
O2—C3—C4	124.99 (12)	H13A—C13—H13B	109.5
N1—C3—C4	121.24 (12)	C12—C13—H13C	109.5
C3—C4—C14	116.88 (12)	H13A—C13—H13C	109.5
C3—C4—C5	122.11 (12)	H13B—C13—H13C	109.5
C14—C4—C5	120.98 (11)	O1—C14—N3	117.45 (11)
N2—C5—C4	115.81 (11)	O1—C14—C4	124.63 (12)
N2—C5—S2	122.21 (10)	N3—C14—C4	117.92 (11)
C4—C5—S2	121.98 (9)	C9—C15—C16	122.49 (13)
C16—C6—C7	118.85 (12)	C9—C15—H15	118.8
C16—C6—N2	126.56 (12)	C16—C15—H15	118.8
C7—C6—N2	114.56 (11)	C6—C16—C15	119.45 (12)
C8—C7—C6	120.49 (12)	C6—C16—H16	120.3
C8—C7—H7	119.8	C15—C16—H16	120.3
C6—C7—H7	119.8	C3—N1—C11	123.34 (11)
C7—C8—C9	121.49 (12)	C3—N1—C2	117.49 (11)
C7—C8—H8	119.3	C11—N1—C2	119.16 (11)
C9—C8—H8	119.3	C5—N2—C6	133.01 (11)
C15—C9—C8	117.22 (13)	C5—N2—H2A	113.5
C15—C9—C10	121.62 (13)	C6—N2—H2A	113.5
C8—C9—C10	121.16 (12)	C11—N3—C14	124.58 (11)
C9—C10—H10A	109.5	C11—N3—C12	119.10 (11)
C9—C10—H10B	109.5	C14—N3—C12	116.26 (10)
H10A—C10—H10B	109.5	C3—O2—H2	109.5
C9—C10—H10C	109.5
O2—C3—C4—C14	−175.61 (12)	C4—C3—N1—C11	−1.66 (19)
N1—C3—C4—C14	2.86 (19)	O2—C3—N1—C2	−1.73 (17)
O2—C3—C4—C5	2.6 (2)	C4—C3—N1—C2	179.63 (12)
N1—C3—C4—C5	−178.90 (12)	N3—C11—N1—C3	2.49 (18)
C3—C4—C5—N2	−179.38 (12)	S1—C11—N1—C3	−177.43 (10)
C14—C4—C5—N2	−1.21 (18)	N3—C11—N1—C2	−178.82 (11)
C3—C4—C5—S2	−0.13 (18)	S1—C11—N1—C2	1.26 (17)
C14—C4—C5—S2	178.04 (10)	C1—C2—N1—C3	89.70 (14)
C16—C6—C7—C8	0.5 (2)	C1—C2—N1—C11	−89.06 (15)
N2—C6—C7—C8	−177.64 (12)	C4—C5—N2—C6	−179.88 (13)
C6—C7—C8—C9	0.2 (2)	S2—C5—N2—C6	0.9 (2)
C7—C8—C9—C15	−1.1 (2)	C16—C6—N2—C5	15.8 (2)
C7—C8—C9—C10	178.74 (13)	C7—C6—N2—C5	−166.23 (14)
C3—C4—C14—O1	175.27 (12)	N1—C11—N3—C14	−5.00 (18)
C5—C4—C14—O1	−3.0 (2)	S1—C11—N3—C14	174.92 (10)
C3—C4—C14—N3	−4.98 (18)	N1—C11—N3—C12	177.82 (11)
C5—C4—C14—N3	176.76 (11)	S1—C11—N3—C12	−2.26 (17)
C8—C9—C15—C16	1.3 (2)	O1—C14—N3—C11	−173.84 (12)
C10—C9—C15—C16	−178.54 (14)	C4—C14—N3—C11	6.40 (18)
C7—C6—C16—C15	−0.3 (2)	O1—C14—N3—C12	3.41 (17)
N2—C6—C16—C15	177.58 (13)	C4—C14—N3—C12	−176.35 (11)
C9—C15—C16—C6	−0.6 (2)	C13—C12—N3—C11	85.26 (15)
O2—C3—N1—C11	176.97 (12)	C13—C12—N3—C14	−92.15 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O2^i	0.95	2.62	3.3136 (16)	130
C13—H13A···S1	0.98	2.95	3.4766 (15)	115
C16—H16···S2	0.95	2.51	3.1509 (14)	125
N2—H2A···O1	0.88	1.79	2.5671 (15)	147
O2—H2···S2	0.84	1.99	2.7802 (10)	157

Symmetry code: (i) x−1, −y+1/2, z−1/2.

5-(1-Aminoethylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (A17)

Crystal data

C10H15N3O2S	F(000) = 1024
Mr = 241.31	Dx = 1.400 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.8983 (4) Å	Cell parameters from 9096 reflections
b = 9.8458 (3) Å	θ = 1.7–28.4°
c = 18.2217 (6) Å	µ = 0.27 mm^−1
β = 98.250 (2)°	T = 100 K
V = 2290.10 (13) Å^3	Block, colourless
Z = 8	0.19 × 0.13 × 0.09 mm

Data collection

Bruker APEXII CCD diffractometer	5036 independent reflections
Radiation source: sealed tube	4323 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 27.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −16→16
Tmin = 0.941, Tmax = 0.985	k = −12→12
14727 measured reflections	l = −23→22

Refinement

Refinement on F^2	3 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.033	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0456P)^2 + 0.8588P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.004
5036 reflections	Δρmax = 0.28 e Å^−3
291 parameters	Δρmin = −0.27 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C6	0.61243 (11)	0.27480 (14)	0.36078 (8)	0.0203 (3)
H6A	0.6519	0.2775	0.3187	0.030*
H6B	0.6093	0.3662	0.3816	0.030*
H6C	0.5412	0.2422	0.3440	0.030*
C7	0.66566 (10)	0.18105 (13)	0.41878 (7)	0.0150 (3)
C10	0.68959 (10)	0.07191 (13)	0.54211 (7)	0.0149 (3)
C4	0.72421 (11)	−0.01292 (14)	0.66991 (8)	0.0191 (3)
H4A	0.7107	0.0230	0.7184	0.023*
H4B	0.7971	0.0108	0.6640	0.023*
C5	0.71329 (12)	−0.16651 (15)	0.67012 (9)	0.0248 (3)
H5A	0.7629	−0.2047	0.7106	0.037*
H5B	0.6417	−0.1909	0.6772	0.037*
H5C	0.7282	−0.2031	0.6227	0.037*
C3	0.55336 (10)	0.09224 (13)	0.62285 (7)	0.0156 (3)
C9	0.53259 (10)	0.21474 (13)	0.50361 (7)	0.0155 (3)
C2	0.38748 (10)	0.20954 (14)	0.57743 (8)	0.0178 (3)
H2A	0.3550	0.1377	0.6046	0.021*
H2B	0.3450	0.2196	0.5280	0.021*
C1	0.38662 (11)	0.34275 (15)	0.61955 (9)	0.0234 (3)
H1A	0.3143	0.3670	0.6246	0.035*
H1B	0.4275	0.3326	0.6689	0.035*
H1C	0.4175	0.4145	0.5923	0.035*
C20	0.15999 (10)	0.69458 (13)	0.29638 (7)	0.0147 (3)
C13	0.00875 (10)	0.80458 (13)	0.33995 (8)	0.0164 (3)
C14	−0.00593 (10)	0.80558 (14)	0.47372 (8)	0.0191 (3)
H14A	−0.0333	0.8988	0.4643	0.023*
H14B	0.0466	0.8081	0.5190	0.023*
C15	−0.09521 (11)	0.71255 (17)	0.48682 (9)	0.0278 (3)
H15A	−0.1269	0.7459	0.5292	0.042*
H15B	−0.1481	0.7112	0.4425	0.042*
H15C	−0.0683	0.6204	0.4973	0.042*
C17	0.27977 (10)	0.55276 (13)	0.38352 (8)	0.0157 (3)
C16	0.34694 (11)	0.51622 (15)	0.32607 (8)	0.0206 (3)
H16A	0.4017	0.4528	0.3474	0.031*
H16B	0.3794	0.5985	0.3095	0.031*
H16C	0.3037	0.4733	0.2837	0.031*
C19	0.13125 (10)	0.67181 (13)	0.42765 (7)	0.0149 (3)
C12	0.02386 (11)	0.79835 (15)	0.20565 (8)	0.0209 (3)
H12A	−0.0535	0.8050	0.1995	0.025*
H12B	0.0422	0.7236	0.1735	0.025*
C11	0.06788 (13)	0.93049 (16)	0.18012 (9)	0.0276 (3)
H11A	0.0390	0.9473	0.1282	0.041*
H11B	0.0486	1.0054	0.2109	0.041*
H11C	0.1444	0.9240	0.1848	0.041*
C8	0.62892 (10)	0.15566 (13)	0.48761 (7)	0.0146 (3)
N2	0.65158 (8)	0.05361 (11)	0.61006 (6)	0.0152 (2)
N3	0.49530 (8)	0.16758 (11)	0.56810 (6)	0.0150 (2)
N1	0.74982 (9)	0.12103 (12)	0.40227 (6)	0.0173 (2)
H1D	0.7846	0.0640	0.4339	0.021*
H1E	0.7716	0.1377	0.3596	0.021*
N5	0.06334 (8)	0.76423 (11)	0.28415 (6)	0.0157 (2)
N6	0.04578 (8)	0.76099 (11)	0.41021 (6)	0.0154 (2)
C18	0.19109 (10)	0.64012 (13)	0.36918 (7)	0.0145 (3)
N4	0.30665 (9)	0.49831 (12)	0.44921 (7)	0.0197 (3)
H4C	0.2697	0.5156	0.4852	0.024*
H4D	0.3616	0.4445	0.4573	0.024*
O1	0.47924 (7)	0.29948 (10)	0.46500 (5)	0.0213 (2)
O2	0.77401 (7)	0.01732 (10)	0.53471 (5)	0.0197 (2)
O3	0.20935 (7)	0.68444 (10)	0.24372 (5)	0.0187 (2)
O4	0.15024 (7)	0.62872 (10)	0.49193 (5)	0.0192 (2)
S1	0.50759 (3)	0.05125 (4)	0.70094 (2)	0.02191 (10)
S2	−0.09755 (3)	0.90311 (4)	0.32209 (2)	0.02713 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C6	0.0229 (7)	0.0194 (7)	0.0191 (7)	0.0044 (6)	0.0048 (5)	0.0033 (5)
C7	0.0151 (6)	0.0133 (6)	0.0162 (6)	−0.0016 (5)	0.0008 (5)	−0.0027 (5)
C10	0.0147 (6)	0.0127 (6)	0.0168 (7)	−0.0016 (5)	0.0009 (5)	−0.0017 (5)
C4	0.0177 (7)	0.0214 (7)	0.0165 (7)	0.0002 (5)	−0.0030 (5)	0.0030 (5)
C5	0.0236 (7)	0.0215 (7)	0.0280 (8)	0.0024 (6)	−0.0004 (6)	0.0059 (6)
C3	0.0176 (6)	0.0138 (6)	0.0151 (6)	−0.0024 (5)	0.0014 (5)	−0.0035 (5)
C9	0.0154 (6)	0.0152 (6)	0.0155 (6)	−0.0002 (5)	0.0010 (5)	−0.0030 (5)
C2	0.0128 (6)	0.0205 (7)	0.0203 (7)	0.0007 (5)	0.0031 (5)	−0.0041 (5)
C1	0.0180 (7)	0.0243 (7)	0.0278 (8)	0.0030 (6)	0.0028 (6)	−0.0085 (6)
C20	0.0137 (6)	0.0114 (6)	0.0186 (6)	−0.0022 (5)	0.0014 (5)	−0.0028 (5)
C13	0.0145 (6)	0.0131 (6)	0.0209 (7)	0.0002 (5)	0.0005 (5)	−0.0020 (5)
C14	0.0174 (6)	0.0205 (7)	0.0202 (7)	0.0027 (5)	0.0050 (5)	−0.0058 (5)
C15	0.0203 (7)	0.0337 (8)	0.0313 (8)	−0.0015 (6)	0.0098 (6)	−0.0033 (7)
C17	0.0139 (6)	0.0129 (6)	0.0201 (7)	−0.0017 (5)	0.0013 (5)	−0.0022 (5)
C16	0.0170 (7)	0.0216 (7)	0.0238 (8)	0.0052 (5)	0.0050 (5)	−0.0003 (6)
C19	0.0126 (6)	0.0129 (6)	0.0190 (7)	−0.0012 (5)	0.0012 (5)	−0.0012 (5)
C12	0.0205 (7)	0.0234 (7)	0.0171 (7)	0.0026 (6)	−0.0032 (5)	−0.0001 (6)
C11	0.0313 (8)	0.0261 (8)	0.0238 (8)	0.0019 (6)	−0.0017 (6)	0.0066 (6)
C8	0.0143 (6)	0.0135 (6)	0.0159 (6)	0.0002 (5)	0.0019 (5)	−0.0011 (5)
N2	0.0148 (5)	0.0154 (5)	0.0146 (6)	0.0007 (4)	0.0000 (4)	0.0010 (4)
N3	0.0134 (5)	0.0153 (5)	0.0165 (6)	0.0008 (4)	0.0028 (4)	−0.0019 (4)
N1	0.0169 (6)	0.0184 (6)	0.0171 (6)	0.0029 (4)	0.0046 (4)	0.0009 (5)
N5	0.0153 (5)	0.0150 (5)	0.0163 (6)	0.0016 (4)	0.0001 (4)	0.0001 (4)
N6	0.0133 (5)	0.0144 (5)	0.0184 (6)	0.0015 (4)	0.0021 (4)	−0.0029 (4)
C18	0.0132 (6)	0.0131 (6)	0.0171 (6)	−0.0004 (5)	0.0022 (5)	−0.0018 (5)
N4	0.0169 (6)	0.0214 (6)	0.0205 (6)	0.0064 (5)	0.0020 (5)	0.0019 (5)
O1	0.0192 (5)	0.0241 (5)	0.0209 (5)	0.0093 (4)	0.0035 (4)	0.0046 (4)
O2	0.0156 (4)	0.0216 (5)	0.0217 (5)	0.0056 (4)	0.0023 (4)	0.0026 (4)
O3	0.0189 (5)	0.0208 (5)	0.0171 (5)	0.0006 (4)	0.0050 (4)	0.0005 (4)
O4	0.0193 (5)	0.0221 (5)	0.0165 (5)	0.0034 (4)	0.0036 (4)	0.0019 (4)
S1	0.02434 (19)	0.02587 (19)	0.01656 (18)	−0.00022 (14)	0.00644 (14)	0.00183 (14)
S2	0.02287 (19)	0.0292 (2)	0.0281 (2)	0.01446 (15)	−0.00076 (15)	−0.00179 (16)

Geometric parameters (Å, º)

C6—C7	1.4940 (18)	C20—C18	1.4338 (19)
C6—H6A	0.9800	C13—N6	1.3695 (18)
C6—H6B	0.9800	C13—N5	1.3758 (17)
C6—H6C	0.9800	C13—S2	1.6729 (13)
C7—N1	1.3083 (17)	C14—N6	1.4828 (16)
C7—C8	1.4251 (18)	C14—C15	1.517 (2)
C10—O2	1.2390 (16)	C14—H14A	0.9900
C10—N2	1.4071 (17)	C14—H14B	0.9900
C10—C8	1.4337 (18)	C15—H15A	0.9800
C4—N2	1.4842 (17)	C15—H15B	0.9800
C4—C5	1.519 (2)	C15—H15C	0.9800
C4—H4A	0.9900	C17—N4	1.3120 (18)
C4—H4B	0.9900	C17—C18	1.4250 (18)
C5—H5A	0.9800	C17—C16	1.4953 (18)
C5—H5B	0.9800	C16—H16A	0.9800
C5—H5C	0.9800	C16—H16B	0.9800
C3—N2	1.3743 (17)	C16—H16C	0.9800
C3—N3	1.3754 (18)	C19—O4	1.2367 (16)
C3—S1	1.6667 (14)	C19—N6	1.4095 (16)
C9—O1	1.2352 (16)	C19—C18	1.4367 (17)
C9—N3	1.4107 (17)	C12—N5	1.4864 (17)
C9—C8	1.4390 (18)	C12—C11	1.519 (2)
C2—N3	1.4838 (16)	C12—H12A	0.9900
C2—C1	1.5204 (19)	C12—H12B	0.9900
C2—H2A	0.9900	C11—H11A	0.9800
C2—H2B	0.9900	C11—H11B	0.9800
C1—H1A	0.9800	C11—H11C	0.9800
C1—H1B	0.9800	N1—H1D	0.8800
C1—H1C	0.9800	N1—H1E	0.8800
C20—O3	1.2294 (16)	N4—H4C	0.8800
C20—N5	1.4123 (16)	N4—H4D	0.8800
C7—C6—H6A	109.5	C14—C15—H15A	109.5
C7—C6—H6B	109.5	C14—C15—H15B	109.5
H6A—C6—H6B	109.5	H15A—C15—H15B	109.5
C7—C6—H6C	109.5	C14—C15—H15C	109.5
H6A—C6—H6C	109.5	H15A—C15—H15C	109.5
H6B—C6—H6C	109.5	H15B—C15—H15C	109.5
N1—C7—C8	120.98 (12)	N4—C17—C18	120.92 (12)
N1—C7—C6	115.39 (12)	N4—C17—C16	115.89 (12)
C8—C7—C6	123.62 (12)	C18—C17—C16	123.19 (12)
O2—C10—N2	117.57 (12)	C17—C16—H16A	109.5
O2—C10—C8	125.10 (12)	C17—C16—H16B	109.5
N2—C10—C8	117.30 (11)	H16A—C16—H16B	109.5
N2—C4—C5	113.10 (11)	C17—C16—H16C	109.5
N2—C4—H4A	109.0	H16A—C16—H16C	109.5
C5—C4—H4A	109.0	H16B—C16—H16C	109.5
N2—C4—H4B	109.0	O4—C19—N6	118.00 (12)
C5—C4—H4B	109.0	O4—C19—C18	124.98 (12)
H4A—C4—H4B	107.8	N6—C19—C18	117.01 (11)
C4—C5—H5A	109.5	N5—C12—C11	113.38 (12)
C4—C5—H5B	109.5	N5—C12—H12A	108.9
H5A—C5—H5B	109.5	C11—C12—H12A	108.9
C4—C5—H5C	109.5	N5—C12—H12B	108.9
H5A—C5—H5C	109.5	C11—C12—H12B	108.9
H5B—C5—H5C	109.5	H12A—C12—H12B	107.7
N2—C3—N3	116.45 (11)	C12—C11—H11A	109.5
N2—C3—S1	121.73 (10)	C12—C11—H11B	109.5
N3—C3—S1	121.81 (10)	H11A—C11—H11B	109.5
O1—C9—N3	117.90 (12)	C12—C11—H11C	109.5
O1—C9—C8	125.76 (13)	H11A—C11—H11C	109.5
N3—C9—C8	116.31 (11)	H11B—C11—H11C	109.5
N3—C2—C1	111.89 (11)	C7—C8—C10	119.54 (11)
N3—C2—H2A	109.2	C7—C8—C9	120.88 (12)
C1—C2—H2A	109.2	C10—C8—C9	119.57 (12)
N3—C2—H2B	109.2	C3—N2—C10	124.04 (11)
C1—C2—H2B	109.2	C3—N2—C4	119.84 (11)
H2A—C2—H2B	107.9	C10—N2—C4	116.12 (11)
C2—C1—H1A	109.5	C3—N3—C9	124.50 (11)
C2—C1—H1B	109.5	C3—N3—C2	119.26 (11)
H1A—C1—H1B	109.5	C9—N3—C2	116.17 (11)
C2—C1—H1C	109.5	C7—N1—H1D	120.0
H1A—C1—H1C	109.5	C7—N1—H1E	120.0
H1B—C1—H1C	109.5	H1D—N1—H1E	120.0
O3—C20—N5	117.43 (12)	C13—N5—C20	123.88 (11)
O3—C20—C18	125.76 (12)	C13—N5—C12	120.33 (11)
N5—C20—C18	116.81 (11)	C20—N5—C12	115.74 (11)
N6—C13—N5	116.97 (11)	C13—N6—C19	124.23 (11)
N6—C13—S2	121.99 (10)	C13—N6—C14	120.08 (11)
N5—C13—S2	121.04 (10)	C19—N6—C14	115.67 (11)
N6—C14—C15	112.37 (11)	C17—C18—C20	120.40 (12)
N6—C14—H14A	109.1	C17—C18—C19	119.85 (12)
C15—C14—H14A	109.1	C20—C18—C19	119.74 (11)
N6—C14—H14B	109.1	C17—N4—H4C	120.0
C15—C14—H14B	109.1	C17—N4—H4D	120.0
H14A—C14—H14B	107.9	H4C—N4—H4D	120.0
N1—C7—C8—C10	5.16 (19)	N6—C13—N5—C20	−7.27 (18)
C6—C7—C8—C10	−175.35 (12)	S2—C13—N5—C20	172.41 (10)
N1—C7—C8—C9	−175.84 (12)	N6—C13—N5—C12	175.36 (11)
C6—C7—C8—C9	3.6 (2)	S2—C13—N5—C12	−4.96 (17)
O2—C10—C8—C7	−0.1 (2)	O3—C20—N5—C13	−167.99 (12)
N2—C10—C8—C7	177.99 (11)	C18—C20—N5—C13	12.88 (18)
O2—C10—C8—C9	−179.13 (12)	O3—C20—N5—C12	9.49 (17)
N2—C10—C8—C9	−1.02 (18)	C18—C20—N5—C12	−169.64 (11)
O1—C9—C8—C7	−7.1 (2)	C11—C12—N5—C13	92.32 (15)
N3—C9—C8—C7	170.88 (11)	C11—C12—N5—C20	−85.25 (15)
O1—C9—C8—C10	171.89 (13)	N5—C13—N6—C19	−4.06 (18)
N3—C9—C8—C10	−10.12 (18)	S2—C13—N6—C19	176.25 (10)
N3—C3—N2—C10	−8.11 (18)	N5—C13—N6—C14	177.13 (11)
S1—C3—N2—C10	172.50 (10)	S2—C13—N6—C14	−2.55 (17)
N3—C3—N2—C4	172.44 (11)	O4—C19—N6—C13	−172.51 (12)
S1—C3—N2—C4	−6.95 (17)	C18—C19—N6—C13	8.68 (18)
O2—C10—N2—C3	−170.97 (12)	O4—C19—N6—C14	6.34 (17)
C8—C10—N2—C3	10.78 (19)	C18—C19—N6—C14	−172.46 (11)
O2—C10—N2—C4	8.51 (17)	C15—C14—N6—C13	88.19 (15)
C8—C10—N2—C4	−169.74 (11)	C15—C14—N6—C19	−90.71 (14)
C5—C4—N2—C3	89.41 (15)	N4—C17—C18—C20	−177.45 (12)
C5—C4—N2—C10	−90.08 (14)	C16—C17—C18—C20	2.01 (19)
N2—C3—N3—C9	−4.72 (18)	N4—C17—C18—C19	1.37 (19)
S1—C3—N3—C9	174.67 (10)	C16—C17—C18—C19	−179.17 (12)
N2—C3—N3—C2	178.38 (11)	O3—C20—C18—C17	−7.7 (2)
S1—C3—N3—C2	−2.23 (17)	N5—C20—C18—C17	171.32 (11)
O1—C9—N3—C3	−168.30 (12)	O3—C20—C18—C19	173.46 (12)
C8—C9—N3—C3	13.55 (18)	N5—C20—C18—C19	−7.50 (18)
O1—C9—N3—C2	8.69 (17)	O4—C19—C18—C17	0.0 (2)
C8—C9—N3—C2	−169.46 (11)	N6—C19—C18—C17	178.75 (11)
C1—C2—N3—C3	87.13 (15)	O4—C19—C18—C20	178.86 (12)
C1—C2—N3—C9	−90.02 (14)	N6—C19—C18—C20	−2.43 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O3^i	0.98	2.43	3.3103 (17)	149
N1—H1D···O2	0.88	1.92	2.5977 (15)	133
N1—H1E···O3^i	0.88	1.99	2.8540 (15)	168
N4—H4C···O4	0.88	1.92	2.6029 (15)	133
N4—H4D···O1	0.88	2.07	2.9473 (15)	172

Symmetry code: (i) −x+1, y−1/2, −z+1/2.

5-(1-Aminopropylidene)-1,3-diethyl-2-thioxodihydropyrimidine-4,6(1H,5H)-dione (A18)

Crystal data

C11H17N3O2S	Dx = 1.383 Mg m^−3
Mr = 255.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 5433 reflections
a = 4.9625 (3) Å	θ = 2.6–27.3°
b = 10.6358 (7) Å	µ = 0.26 mm^−1
c = 23.2402 (15) Å	T = 100 K
V = 1226.62 (14) Å^3	Rod, orange
Z = 4	0.25 × 0.11 × 0.09 mm
F(000) = 544

Data collection

Bruker APEXII CCD diffractometer	10534 independent reflections
Radiation source: sealed tube	9991 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.000
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −6→6
Tmin = 0.924, Tmax = 0.988	k = −13→13
10534 measured reflections	l = −30→28

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.032	w = 1/[σ^2(Fo^2) + (0.0273P)^2 + 0.4988P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.076	(Δ/σ)max = 0.001
S = 1.03	Δρmax = 0.28 e Å^−3
10534 reflections	Δρmin = −0.22 e Å^−3
154 parameters	Absolute structure: Flack x determined using 1038 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: −0.02 (3)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.6440 (6)	0.8030 (2)	0.90953 (10)	0.0193 (5)
H1A	0.614519	0.878231	0.933081	0.029*
H1B	0.830720	0.774705	0.913955	0.029*
H1C	0.609323	0.823020	0.869034	0.029*
C2	0.4537 (5)	0.6994 (2)	0.92894 (10)	0.0176 (6)
H2A	0.486896	0.680627	0.970053	0.021*
H2B	0.265388	0.728966	0.925109	0.021*
C3	0.6710 (5)	0.4948 (2)	0.91284 (9)	0.0165 (5)
C4	0.8881 (5)	0.2876 (2)	0.89628 (11)	0.0187 (6)
H4A	1.043489	0.326064	0.916389	0.022*
H4B	0.956508	0.245498	0.861222	0.022*
C5	0.7578 (6)	0.1907 (3)	0.93530 (11)	0.0259 (7)
H5A	0.890515	0.126206	0.945486	0.039*
H5B	0.692791	0.231900	0.970376	0.039*
H5C	0.605865	0.151385	0.915244	0.039*
C6	−0.1787 (6)	0.4847 (2)	0.68889 (11)	0.0237 (6)
H6A	−0.297294	0.553048	0.676335	0.035*
H6B	−0.056686	0.461776	0.657430	0.035*
H6C	−0.287702	0.411508	0.699611	0.035*
C7	−0.0142 (5)	0.5278 (2)	0.74073 (10)	0.0159 (5)
H7A	0.089865	0.603344	0.729509	0.019*
H7B	−0.140542	0.553209	0.771579	0.019*
C8	0.1772 (5)	0.4330 (2)	0.76485 (10)	0.0147 (5)
C9	0.3485 (5)	0.4573 (2)	0.81314 (10)	0.0135 (5)
C10	0.5338 (5)	0.3619 (2)	0.83171 (10)	0.0150 (5)
C11	0.3302 (5)	0.5736 (2)	0.84439 (10)	0.0145 (5)
N1	0.4895 (4)	0.58329 (19)	0.89474 (8)	0.0146 (5)
N2	0.6952 (4)	0.38770 (18)	0.87954 (8)	0.0147 (5)
O1	0.5626 (4)	0.25808 (16)	0.80789 (7)	0.0204 (4)
O2	0.1876 (4)	0.66376 (16)	0.83154 (7)	0.0205 (4)
N3	0.1851 (5)	0.32251 (19)	0.73951 (8)	0.0185 (5)
H3A	0.295382	0.263996	0.752250	0.022*
H3B	0.080206	0.307096	0.709809	0.022*
S1	0.85678 (15)	0.51436 (6)	0.97179 (3)	0.02579 (18)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0194 (14)	0.0181 (13)	0.0205 (13)	0.0008 (12)	−0.0006 (12)	−0.0028 (10)
C2	0.0162 (13)	0.0207 (14)	0.0158 (12)	0.0013 (11)	0.0010 (10)	−0.0055 (11)
C3	0.0150 (12)	0.0178 (13)	0.0168 (12)	−0.0028 (12)	0.0009 (9)	0.0027 (10)
C4	0.0165 (14)	0.0193 (14)	0.0203 (13)	0.0043 (11)	−0.0024 (11)	0.0031 (10)
C5	0.0295 (17)	0.0211 (14)	0.0269 (15)	−0.0008 (12)	−0.0015 (12)	0.0086 (12)
C6	0.0252 (15)	0.0207 (14)	0.0251 (13)	0.0009 (13)	−0.0074 (11)	−0.0006 (12)
C7	0.0141 (12)	0.0152 (13)	0.0183 (12)	0.0005 (11)	−0.0011 (10)	0.0013 (10)
C8	0.0140 (13)	0.0143 (12)	0.0157 (12)	−0.0003 (11)	0.0036 (10)	0.0026 (10)
C9	0.0126 (12)	0.0140 (12)	0.0138 (11)	−0.0001 (10)	0.0018 (10)	0.0008 (9)
C10	0.0135 (13)	0.0168 (13)	0.0149 (12)	−0.0017 (10)	0.0022 (10)	0.0027 (10)
C11	0.0120 (13)	0.0170 (12)	0.0143 (12)	−0.0022 (11)	0.0007 (10)	0.0019 (10)
N1	0.0142 (11)	0.0155 (11)	0.0141 (11)	0.0002 (9)	−0.0003 (9)	−0.0005 (9)
N2	0.0134 (11)	0.0133 (10)	0.0173 (10)	0.0001 (9)	−0.0014 (9)	0.0025 (8)
O1	0.0221 (11)	0.0159 (10)	0.0232 (10)	0.0044 (8)	−0.0022 (8)	−0.0034 (8)
O2	0.0219 (11)	0.0170 (9)	0.0226 (9)	0.0058 (8)	−0.0049 (8)	−0.0016 (7)
N3	0.0225 (13)	0.0158 (11)	0.0173 (10)	0.0022 (10)	−0.0053 (9)	−0.0017 (9)
S1	0.0308 (4)	0.0239 (4)	0.0227 (3)	−0.0017 (3)	−0.0131 (3)	0.0009 (3)

Geometric parameters (Å, º)

C1—C2	1.520 (4)	C6—C7	1.526 (3)
C1—H1A	0.9800	C6—H6A	0.9800
C1—H1B	0.9800	C6—H6B	0.9800
C1—H1C	0.9800	C6—H6C	0.9800
C2—N1	1.480 (3)	C7—C8	1.494 (3)
C2—H2A	0.9900	C7—H7A	0.9900
C2—H2B	0.9900	C7—H7B	0.9900
C3—N1	1.369 (3)	C8—N3	1.315 (3)
C3—N2	1.383 (3)	C8—C9	1.432 (3)
C3—S1	1.664 (2)	C9—C10	1.436 (3)
C4—N2	1.483 (3)	C9—C11	1.437 (3)
C4—C5	1.518 (3)	C10—O1	1.243 (3)
C4—H4A	0.9900	C10—N2	1.398 (3)
C4—H4B	0.9900	C11—O2	1.228 (3)
C5—H5A	0.9800	C11—N1	1.416 (3)
C5—H5B	0.9800	N3—H3A	0.8800
C5—H5C	0.9800	N3—H3B	0.8800
C2—C1—H1A	109.5	C7—C6—H6C	109.5
C2—C1—H1B	109.5	H6A—C6—H6C	109.5
H1A—C1—H1B	109.5	H6B—C6—H6C	109.5
C2—C1—H1C	109.5	C8—C7—C6	115.7 (2)
H1A—C1—H1C	109.5	C8—C7—H7A	108.4
H1B—C1—H1C	109.5	C6—C7—H7A	108.4
N1—C2—C1	111.8 (2)	C8—C7—H7B	108.4
N1—C2—H2A	109.3	C6—C7—H7B	108.4
C1—C2—H2A	109.3	H7A—C7—H7B	107.4
N1—C2—H2B	109.3	N3—C8—C9	119.7 (2)
C1—C2—H2B	109.3	N3—C8—C7	117.0 (2)
H2A—C2—H2B	107.9	C9—C8—C7	123.3 (2)
N1—C3—N2	116.8 (2)	C8—C9—C10	119.2 (2)
N1—C3—S1	122.12 (18)	C8—C9—C11	121.0 (2)
N2—C3—S1	121.03 (19)	C10—C9—C11	119.8 (2)
N2—C4—C5	111.7 (2)	O1—C10—N2	117.6 (2)
N2—C4—H4A	109.3	O1—C10—C9	124.6 (2)
C5—C4—H4A	109.3	N2—C10—C9	117.8 (2)
N2—C4—H4B	109.3	O2—C11—N1	117.8 (2)
C5—C4—H4B	109.3	O2—C11—C9	125.8 (2)
H4A—C4—H4B	107.9	N1—C11—C9	116.4 (2)
C4—C5—H5A	109.5	C3—N1—C11	124.9 (2)
C4—C5—H5B	109.5	C3—N1—C2	119.2 (2)
H5A—C5—H5B	109.5	C11—N1—C2	115.9 (2)
C4—C5—H5C	109.5	C3—N2—C10	123.9 (2)
H5A—C5—H5C	109.5	C3—N2—C4	120.0 (2)
H5B—C5—H5C	109.5	C10—N2—C4	115.9 (2)
C7—C6—H6A	109.5	C8—N3—H3A	120.0
C7—C6—H6B	109.5	C8—N3—H3B	120.0
H6A—C6—H6B	109.5	H3A—N3—H3B	120.0
C6—C7—C8—N3	−0.2 (3)	S1—C3—N1—C2	−0.8 (3)
C6—C7—C8—C9	179.6 (2)	O2—C11—N1—C3	−175.6 (2)
N3—C8—C9—C10	2.3 (4)	C9—C11—N1—C3	5.1 (3)
C7—C8—C9—C10	−177.5 (2)	O2—C11—N1—C2	3.7 (3)
N3—C8—C9—C11	−175.3 (2)	C9—C11—N1—C2	−175.6 (2)
C7—C8—C9—C11	4.9 (4)	C1—C2—N1—C3	90.0 (3)
C8—C9—C10—O1	1.7 (4)	C1—C2—N1—C11	−89.4 (3)
C11—C9—C10—O1	179.4 (2)	N1—C3—N2—C10	−4.6 (3)
C8—C9—C10—N2	−179.0 (2)	S1—C3—N2—C10	175.80 (18)
C11—C9—C10—N2	−1.3 (3)	N1—C3—N2—C4	179.9 (2)
C8—C9—C11—O2	−5.3 (4)	S1—C3—N2—C4	0.3 (3)
C10—C9—C11—O2	177.1 (2)	O1—C10—N2—C3	−174.9 (2)
C8—C9—C11—N1	174.0 (2)	C9—C10—N2—C3	5.7 (3)
C10—C9—C11—N1	−3.7 (3)	O1—C10—N2—C4	0.8 (3)
N2—C3—N1—C11	−1.1 (3)	C9—C10—N2—C4	−178.6 (2)
S1—C3—N1—C11	178.49 (19)	C5—C4—N2—C3	90.3 (3)
N2—C3—N1—C2	179.6 (2)	C5—C4—N2—C10	−85.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···S1^i	0.98	2.80	3.662 (3)	147
C7—H7A···O1^ii	0.99	2.54	3.507 (3)	166
N3—H3A···O1	0.88	1.85	2.550 (3)	135
N3—H3B···O2^iii	0.88	2.24	3.000 (3)	145

Symmetry codes: (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.