6-Propyl-2-thio­uracil versus 6-meth­oxy­methyl-2-thio­uracil: enhancing the hydrogen-bonded synthon motif by replacement of a methyl­ene group with an O atom

Hützler, W.M.; Egert, E.; Bolte, M.

doi:10.1107/S2053229616011281

6-Propyl-2-thiouracil versus 6-methoxymethyl-2-thiouracil: enhancing the hydrogen-bonded synthon motif by replacement of a methylene group with an O atom

The understanding of intermolecular interactions is a key objective of crystal engineering in order to exploit the derived knowledge for the rational design of new molecular solids with tailored physical and chemical properties. The tools and theories of crystal engineering are indispensable for the rational design of (pharmaceutical) cocrystals. The results of cocrystallization experiments of the antithyroid drug 6-propyl-2-thiouracil (PTU) with 2,4-diaminopyrimidine (DAPY), and of 6-methoxymethyl-2-thiouracil (MOMTU) with DAPY and 2,4,6-triaminopyrimidine (TAPY), respectively, are reported. PTU and MOMTU show a high structural similarity and differ only in the replacement of a methylene group (-CH₂-) with an O atom in the side chain, thus introducing an additional hydrogen-bond acceptor in MOMTU. Both molecules contain an ADA hydrogen-bonding site (A = acceptor and D = donor), while the coformers DAPY and TAPY both show complementary DAD sites and therefore should be capable of forming a mixed ADA/DAD synthon with each other, i.e. N-H

O, N-H

N and N-H

S hydrogen bonds. The experiments yielded one solvated cocrystal salt of PTU with DAPY, four different solvates of MOMTU, one ionic cocrystal of MOMTU with DAPY and one cocrystal salt of MOMTU with TAPY, namely 2,4-diaminopyrimidinium 6-propyl-2-thiouracilate-2,4-diaminopyrimidine-N,N-dimethylacetamide-water (1/1/1/1) (the systematic name for 6-propyl-2-thiouracilate is 6-oxo-4-propyl-2-sulfanylidene-1,2,3,6-tetrahydropyrimidin-1-ide), C₄H₇N₄⁺·C₇H₉N₂OS^-·C₄H₆N₄·C₄H₉NO·H₂O, (I), 6-methoxymethyl-2-thiouracil-N,N-dimethylformamide (1/1), C₆H₈N₂O₂S·C₃H₇NO, (II), 6-methoxymethyl-2-thiouracil-N,N-dimethylacetamide (1/1), C₆H₈N₂O₂S·C₄H₉NO, (III), 6-methoxymethyl-2-thiouracil-dimethyl sulfoxide (1/1), C₆H₈N₂O₂S·C₂H₆OS, (IV), 6-methoxymethyl-2-thiouracil-1-methylpyrrolidin-2-one (1/1), C₆H₈N₂O₂S·C₅H₉NO, (V), 2,4-diaminopyrimidinium 6-methoxymethyl-2-thiouracilate (the systematic name for 6-methoxymethyl-2-thiouracilate is 4-methoxymethyl-6-oxo-2-sulfanylidene-1,2,3,6-tetrahydropyrimidin-1-ide), C₄H₇N₄⁺·C₆H₇N₂O₂S^-, (VI), and 2,4,6-triaminopyrimidinium 6-methoxymethyl-2-thiouracilate-6-methoxymethyl-2-thiouracil (1/1), C₄H₈N₅⁺·C₆H₇N₂O₂S^-·C₆H₈N₂O₂S, (VII). Whereas in (I) only an AA/DD hydrogen-bonding interaction was formed, the structures of (VI) and (VII) both display the desired ADA/DAD synthon. Conformational studies on the side chains of PTU and MOMTU also revealed a significant deviation for cocrystals (VI) and (VII), leading to the desired enhancement of the hydrogen-bond pattern within the crystal.

Keywords: antithyroid drug; crystal engineering; cocrystallization; crystal structure; 6-propyl-2-thiouracil; 6-methoxymethyl-2-thiouracil; hydrogen bonding; PTU; MOMTU.

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616011281/sk3632sup1.cif Contains datablocks I, II, III, IV, V, VI, VII, New_Global_Publ_Block
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011281/sk3632Isup2.hkl Contains datablock I
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011281/sk3632IIsup3.hkl Contains datablock II
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011281/sk3632IIIsup4.hkl Contains datablock III
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011281/sk3632IVsup5.hkl Contains datablock IV
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011281/sk3632Vsup6.hkl Contains datablock V
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011281/sk3632VIsup7.hkl Contains datablock VI
	Structure factor file (CIF format) https://doi.org/10.1107/S2053229616011281/sk3632VIIsup8.hkl Contains datablock VII

CCDC references: 1492078; 1492077; 1492076; 1492075; 1492074; 1492073; 1492072

Computing details top

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) 2,4-Diaminopyrimidinium 6-propyl-2-thiouracilate–2,4-diaminopyrimidine–N,N-dimethylacetamide–water (1/1/1/1) top

Crystal data top

C₄H₇N₄⁺·C₇H₉N₂OS⁻·C₄H₆N₄·C₄H₉NO·H₂O	Z = 2
M_r = 495.62	F(000) = 528
Triclinic, P1	D_x = 1.366 Mg m⁻³
a = 7.9688 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.2412 (15) Å	Cell parameters from 14644 reflections
c = 14.6144 (19) Å	θ = 3.5–26.3°
α = 109.442 (10)°	µ = 0.18 mm⁻¹
β = 92.075 (11)°	T = 173 K
γ = 100.877 (11)°	Block, colourless
V = 1205.4 (3) Å³	0.38 × 0.36 × 0.21 mm

Data collection top

Stoe IPDS II two-circle diffractometer	3603 reflections with I > 2σ(I)
ω scans	R_int = 0.032
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	θ_max = 25.9°, θ_min = 3.5°
T_min = 0.603, T_max = 1.000	h = −9→9
9557 measured reflections	k = −13→11
4597 independent reflections	l = −17→17

Refinement top

Refinement on F²	35 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.054P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
4597 reflections	Δρ_max = 0.19 e Å⁻³
366 parameters	Δρ_min = −0.20 e Å⁻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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.51428 (17)	0.85642 (13)	0.35474 (9)	0.0224 (3)
H1A	0.468 (2)	0.8413 (18)	0.2952 (11)	0.027*
C2A	0.44781 (19)	0.77685 (15)	0.40334 (11)	0.0216 (3)
S21A	0.26827 (5)	0.65970 (4)	0.34882 (3)	0.02654 (12)
N3A	0.52164 (16)	0.79135 (13)	0.49124 (9)	0.0222 (3)
C4A	0.66143 (19)	0.88909 (16)	0.53404 (11)	0.0228 (3)
O41A	0.72441 (14)	0.90499 (11)	0.61940 (8)	0.0274 (3)
C5A	0.7323 (2)	0.97072 (16)	0.48180 (11)	0.0248 (3)
H5A	0.8321	1.0368	0.5097	0.030*
C6A	0.65715 (19)	0.95369 (16)	0.39266 (11)	0.0232 (3)
C7A	0.7142 (2)	1.03117 (17)	0.32944 (11)	0.0293 (4)
H7A1	0.6139	1.0597	0.3085	0.035*
H7A2	0.7527	0.9743	0.2701	0.035*
C8A	0.8573 (2)	1.14874 (17)	0.37629 (12)	0.0272 (4)
H8A1	0.9588	1.1217	0.3975	0.033*
H8A2	0.8195	1.2078	0.4348	0.033*
C9A	0.9076 (2)	1.21998 (19)	0.30578 (13)	0.0363 (4)
H9A1	0.9528	1.1637	0.2499	0.055*
H9A2	0.9959	1.2980	0.3392	0.055*
H9A3	0.8063	1.2441	0.2828	0.055*
N1B	0.38988 (17)	0.60096 (14)	0.56980 (9)	0.0248 (3)
H1B	0.428 (2)	0.6611 (17)	0.5413 (13)	0.030*
C2B	0.4700 (2)	0.61183 (16)	0.65706 (11)	0.0235 (3)
N21B	0.60890 (19)	0.70450 (15)	0.69387 (11)	0.0317 (3)
H21B	0.643 (3)	0.7629 (18)	0.6656 (14)	0.038*
H22B	0.661 (2)	0.714 (2)	0.7480 (12)	0.038*
N3B	0.41373 (17)	0.53316 (14)	0.70571 (9)	0.0255 (3)
C4B	0.2757 (2)	0.43810 (16)	0.66475 (12)	0.0257 (3)
N41B	0.2244 (2)	0.35909 (16)	0.71302 (11)	0.0336 (3)
H41B	0.290 (2)	0.366 (2)	0.7646 (13)	0.040*
H42B	0.139 (2)	0.2924 (18)	0.6887 (14)	0.040*
C5B	0.1860 (2)	0.42229 (17)	0.57334 (12)	0.0306 (4)
H5B	0.0871	0.3554	0.5453	0.037*
C6B	0.2478 (2)	0.50628 (17)	0.52897 (12)	0.0288 (4)
H6B	0.1914	0.4993	0.4684	0.035*
N1C	0.44880 (18)	0.64827 (14)	−0.00738 (9)	0.0282 (3)
C2C	0.43674 (19)	0.68453 (16)	0.08921 (11)	0.0238 (3)
N21C	0.47227 (19)	0.60313 (15)	0.13482 (10)	0.0282 (3)
H21C	0.481 (2)	0.5263 (16)	0.0978 (13)	0.034*
H22C	0.426 (2)	0.611 (2)	0.1893 (12)	0.034*
N3C	0.39832 (17)	0.79512 (13)	0.14604 (9)	0.0243 (3)
C4C	0.3619 (2)	0.87596 (16)	0.10151 (11)	0.0253 (3)
N41C	0.3222 (2)	0.98561 (15)	0.15690 (11)	0.0328 (3)
H41C	0.308 (3)	0.998 (2)	0.2180 (12)	0.039*
H42C	0.284 (3)	1.0359 (19)	0.1295 (14)	0.039*
C5C	0.3690 (2)	0.84510 (18)	−0.00032 (12)	0.0298 (4)
H5C	0.3433	0.9010	−0.0328	0.036*
C6C	0.4139 (2)	0.73251 (18)	−0.04926 (12)	0.0301 (4)
H6C	0.4213	0.7114	−0.1173	0.036*
O1W	0.94931 (16)	1.14740 (14)	0.70712 (10)	0.0372 (3)
H11W	0.880 (2)	1.1958 (16)	0.7042 (15)	0.045*
H12W	0.896 (2)	1.0701 (10)	0.6764 (14)	0.045*
C1X	0.1515 (3)	1.1099 (2)	−0.06990 (14)	0.0456 (5)
H1XA	0.0398	1.0902	−0.1082	0.068*	0.670 (6)
H1XB	0.1793	1.0297	−0.0674	0.068*	0.670 (6)
H1XC	0.2403	1.1518	−0.1005	0.068*	0.670 (6)
H1XD	0.1277	1.0916	−0.1401	0.068*	0.330 (6)
H1XE	0.2747	1.1191	−0.0536	0.068*	0.330 (6)
H1XF	0.0868	1.0386	−0.0525	0.068*	0.330 (6)
O21X	0.18737 (17)	1.18464 (14)	0.11191 (9)	0.0394 (3)
C31X	0.0683 (3)	1.3918 (2)	0.13807 (14)	0.0434 (5)
H3XA	0.1269	1.4801	0.1462	0.065*	0.670 (6)
H3XB	0.1210	1.3637	0.1868	0.065*	0.670 (6)
H3XC	−0.0535	1.3893	0.1468	0.065*	0.670 (6)
H3XD	0.0283	1.4273	0.0905	0.065*	0.330 (6)
H3XE	−0.0254	1.3738	0.1763	0.065*	0.330 (6)
H3XF	0.1653	1.4545	0.1818	0.065*	0.330 (6)
C32X	0.0475 (3)	1.3351 (2)	−0.04973 (14)	0.0455 (5)
H4XA	0.1482	1.3937	−0.0587	0.068*	0.670 (6)
H4XB	−0.0509	1.3770	−0.0418	0.068*	0.670 (6)
H4XC	0.0207	1.2557	−0.1070	0.068*	0.670 (6)
H4XD	0.0301	1.3015	−0.1212	0.068*	0.330 (6)
H4XE	−0.0591	1.3561	−0.0239	0.068*	0.330 (6)
H4XF	0.1393	1.4131	−0.0277	0.068*	0.330 (6)
C2X	0.1435 (3)	1.1999 (3)	0.0332 (2)	0.0291 (8)	0.670 (6)
N3X	0.0845 (3)	1.3035 (3)	0.0379 (2)	0.0314 (8)	0.670 (6)
C2X'	0.1261 (6)	1.2661 (5)	0.0841 (4)	0.0249 (16)	0.330 (6)
N3X'	0.0975 (5)	1.2343 (5)	−0.0134 (3)	0.0258 (15)	0.330 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0256 (6)	0.0212 (7)	0.0185 (6)	0.0026 (5)	0.0025 (5)	0.0057 (5)
C2A	0.0240 (7)	0.0193 (8)	0.0215 (7)	0.0071 (6)	0.0065 (6)	0.0056 (6)
S21A	0.0276 (2)	0.0242 (2)	0.0240 (2)	−0.00230 (16)	0.00039 (15)	0.00779 (16)
N3A	0.0231 (6)	0.0207 (7)	0.0220 (6)	0.0034 (5)	0.0027 (5)	0.0071 (5)
C4A	0.0229 (7)	0.0219 (8)	0.0245 (8)	0.0079 (6)	0.0047 (6)	0.0073 (6)
O41A	0.0298 (6)	0.0279 (7)	0.0239 (6)	0.0013 (5)	−0.0023 (4)	0.0113 (5)
C5A	0.0236 (8)	0.0231 (9)	0.0257 (8)	0.0007 (6)	0.0037 (6)	0.0081 (7)
C6A	0.0232 (7)	0.0222 (8)	0.0230 (7)	0.0048 (6)	0.0060 (6)	0.0062 (6)
C7A	0.0338 (9)	0.0295 (9)	0.0225 (8)	−0.0012 (7)	0.0031 (6)	0.0106 (7)
C8A	0.0266 (8)	0.0256 (9)	0.0287 (8)	0.0027 (7)	0.0065 (6)	0.0098 (7)
C9A	0.0396 (10)	0.0311 (10)	0.0379 (9)	0.0000 (8)	0.0120 (8)	0.0147 (8)
N1B	0.0278 (7)	0.0232 (8)	0.0248 (7)	0.0052 (6)	0.0040 (5)	0.0101 (6)
C2B	0.0259 (8)	0.0213 (8)	0.0238 (7)	0.0076 (6)	0.0051 (6)	0.0066 (6)
N21B	0.0336 (8)	0.0300 (8)	0.0299 (7)	−0.0044 (6)	−0.0034 (6)	0.0151 (6)
N3B	0.0271 (7)	0.0238 (7)	0.0257 (7)	0.0033 (6)	0.0030 (5)	0.0099 (6)
C4B	0.0247 (8)	0.0230 (9)	0.0307 (8)	0.0061 (7)	0.0052 (6)	0.0102 (7)
N41B	0.0311 (8)	0.0328 (9)	0.0381 (8)	−0.0028 (7)	−0.0006 (6)	0.0194 (7)
C5B	0.0285 (8)	0.0271 (9)	0.0328 (9)	0.0009 (7)	−0.0011 (7)	0.0094 (7)
C6B	0.0290 (8)	0.0286 (9)	0.0269 (8)	0.0048 (7)	−0.0011 (6)	0.0082 (7)
N1C	0.0346 (7)	0.0257 (8)	0.0221 (7)	0.0043 (6)	0.0039 (5)	0.0065 (6)
C2C	0.0216 (7)	0.0236 (9)	0.0240 (7)	0.0011 (6)	0.0022 (6)	0.0073 (7)
N21C	0.0390 (8)	0.0244 (8)	0.0230 (7)	0.0097 (6)	0.0071 (6)	0.0083 (6)
N3C	0.0260 (7)	0.0240 (7)	0.0214 (6)	0.0037 (6)	0.0025 (5)	0.0068 (6)
C4C	0.0226 (7)	0.0256 (9)	0.0271 (8)	0.0031 (6)	0.0024 (6)	0.0096 (7)
N41C	0.0456 (9)	0.0309 (9)	0.0261 (7)	0.0151 (7)	0.0066 (6)	0.0111 (7)
C5C	0.0339 (9)	0.0309 (10)	0.0263 (8)	0.0046 (7)	0.0014 (7)	0.0134 (7)
C6C	0.0364 (9)	0.0307 (10)	0.0220 (8)	0.0044 (7)	0.0039 (7)	0.0090 (7)
O1W	0.0301 (6)	0.0309 (7)	0.0447 (7)	0.0002 (5)	−0.0005 (5)	0.0094 (6)
C1X	0.0442 (11)	0.0476 (13)	0.0343 (10)	0.0136 (10)	0.0049 (8)	−0.0017 (9)
O21X	0.0417 (7)	0.0465 (9)	0.0371 (7)	0.0108 (6)	0.0009 (5)	0.0234 (6)
C31X	0.0524 (12)	0.0326 (11)	0.0365 (10)	0.0072 (9)	0.0084 (8)	0.0013 (8)
C32X	0.0541 (12)	0.0495 (13)	0.0395 (10)	0.0077 (10)	−0.0024 (9)	0.0263 (10)
C2X	0.0237 (13)	0.0339 (18)	0.0300 (17)	0.0029 (12)	0.0028 (11)	0.0131 (15)
N3X	0.0357 (13)	0.0298 (16)	0.0285 (15)	0.0055 (11)	0.0022 (10)	0.0108 (13)
C2X'	0.026 (3)	0.026 (3)	0.024 (3)	0.004 (2)	0.003 (2)	0.010 (3)
N3X'	0.027 (2)	0.030 (3)	0.019 (3)	0.006 (2)	0.0009 (18)	0.007 (2)

Geometric parameters (Å, º) top

N1A—C2A	1.363 (2)	N21C—H22C	0.875 (15)
N1A—C6A	1.371 (2)	N3C—C4C	1.346 (2)
N1A—H1A	0.881 (14)	C4C—N41C	1.333 (2)
C2A—N3A	1.3389 (19)	C4C—C5C	1.417 (2)
C2A—S21A	1.7099 (16)	N41C—H41C	0.871 (15)
N3A—C4A	1.367 (2)	N41C—H42C	0.883 (16)
C4A—O41A	1.2698 (19)	C5C—C6C	1.352 (3)
C4A—C5A	1.430 (2)	C5C—H5C	0.9500
C5A—C6A	1.352 (2)	C6C—H6C	0.9500
C5A—H5A	0.9500	O1W—H11W	0.854 (9)
C6A—C7A	1.495 (2)	O1W—H12W	0.851 (9)
C7A—C8A	1.513 (2)	C1X—C2X	1.521 (4)
C7A—H7A1	0.9900	C1X—N3X'	1.519 (5)
C7A—H7A2	0.9900	C1X—H1XA	0.9800
C8A—C9A	1.524 (2)	C1X—H1XB	0.9800
C8A—H8A1	0.9900	C1X—H1XC	0.9800
C8A—H8A2	0.9900	C1X—H1XD	0.9800
C9A—H9A1	0.9800	C1X—H1XE	0.9800
C9A—H9A2	0.9800	C1X—H1XF	0.9800
C9A—H9A3	0.9800	O21X—C2X	1.265 (3)
N1B—C6B	1.358 (2)	O21X—C2X'	1.282 (5)
N1B—C2B	1.363 (2)	C31X—N3X	1.496 (3)
N1B—H1B	0.919 (15)	C31X—C2X'	1.536 (5)
C2B—N21B	1.322 (2)	C31X—H3XA	0.9800
C2B—N3B	1.334 (2)	C31X—H3XB	0.9800
N21B—H21B	0.892 (16)	C31X—H3XC	0.9800
N21B—H22B	0.846 (15)	C31X—H3XD	0.9800
N3B—C4B	1.339 (2)	C31X—H3XE	0.9800
C4B—N41B	1.325 (2)	C31X—H3XF	0.9800
C4B—C5B	1.432 (2)	C32X—N3X	1.473 (3)
N41B—H41B	0.875 (15)	C32X—N3X'	1.511 (5)
N41B—H42B	0.876 (16)	C32X—H4XA	0.9800
C5B—C6B	1.345 (3)	C32X—H4XB	0.9800
C5B—H5B	0.9500	C32X—H4XC	0.9800
C6B—H6B	0.9500	C32X—H4XD	0.9800
N1C—C2C	1.345 (2)	C32X—H4XE	0.9800
N1C—C6C	1.350 (2)	C32X—H4XF	0.9800
C2C—N3C	1.343 (2)	C2X—N3X	1.319 (4)
C2C—N21C	1.361 (2)	C2X'—N3X'	1.347 (7)
N21C—H21C	0.870 (15)

C2A—N1A—C6A	122.29 (13)	C2C—N3C—C4C	116.90 (13)
C2A—N1A—H1A	118.8 (13)	N41C—C4C—N3C	117.56 (15)
C6A—N1A—H1A	118.8 (13)	N41C—C4C—C5C	121.91 (16)
N3A—C2A—N1A	120.44 (14)	N3C—C4C—C5C	120.52 (15)
N3A—C2A—S21A	121.60 (12)	C4C—N41C—H41C	119.7 (15)
N1A—C2A—S21A	117.96 (11)	C4C—N41C—H42C	120.1 (14)
C2A—N3A—C4A	119.91 (14)	H41C—N41C—H42C	118 (2)
O41A—C4A—N3A	118.89 (14)	C6C—C5C—C4C	117.06 (16)
O41A—C4A—C5A	121.84 (14)	C6C—C5C—H5C	121.5
N3A—C4A—C5A	119.27 (13)	C4C—C5C—H5C	121.5
C6A—C5A—C4A	119.91 (15)	N1C—C6C—C5C	124.07 (15)
C6A—C5A—H5A	120.0	N1C—C6C—H6C	118.0
C4A—C5A—H5A	120.0	C5C—C6C—H6C	118.0
C5A—C6A—N1A	118.12 (15)	H11W—O1W—H12W	106.5 (17)
C5A—C6A—C7A	126.41 (15)	C2X—C1X—H1XA	109.5
N1A—C6A—C7A	115.47 (13)	C2X—C1X—H1XB	109.5
C6A—C7A—C8A	115.43 (13)	H1XA—C1X—H1XB	109.5
C6A—C7A—H7A1	108.4	C2X—C1X—H1XC	109.5
C8A—C7A—H7A1	108.4	H1XA—C1X—H1XC	109.5
C6A—C7A—H7A2	108.4	H1XB—C1X—H1XC	109.5
C8A—C7A—H7A2	108.4	N3X'—C1X—H1XD	109.5
H7A1—C7A—H7A2	107.5	N3X'—C1X—H1XE	109.5
C7A—C8A—C9A	111.40 (14)	H1XD—C1X—H1XE	109.5
C7A—C8A—H8A1	109.3	N3X'—C1X—H1XF	109.5
C9A—C8A—H8A1	109.3	H1XD—C1X—H1XF	109.5
C7A—C8A—H8A2	109.3	H1XE—C1X—H1XF	109.5
C9A—C8A—H8A2	109.3	N3X—C31X—H3XA	109.5
H8A1—C8A—H8A2	108.0	N3X—C31X—H3XB	109.5
C8A—C9A—H9A1	109.5	H3XA—C31X—H3XB	109.5
C8A—C9A—H9A2	109.5	N3X—C31X—H3XC	109.5
H9A1—C9A—H9A2	109.5	H3XA—C31X—H3XC	109.5
C8A—C9A—H9A3	109.5	H3XB—C31X—H3XC	109.5
H9A1—C9A—H9A3	109.5	C2X'—C31X—H3XD	109.5
H9A2—C9A—H9A3	109.5	C2X'—C31X—H3XE	109.5
C6B—N1B—C2B	119.72 (15)	H3XD—C31X—H3XE	109.5
C6B—N1B—H1B	120.6 (12)	C2X'—C31X—H3XF	109.5
C2B—N1B—H1B	119.5 (12)	H3XD—C31X—H3XF	109.5
N21B—C2B—N3B	119.55 (15)	H3XE—C31X—H3XF	109.5
N21B—C2B—N1B	117.83 (15)	N3X—C32X—H4XA	109.5
N3B—C2B—N1B	122.62 (15)	N3X—C32X—H4XB	109.5
C2B—N21B—H21B	120.9 (13)	H4XA—C32X—H4XB	109.5
C2B—N21B—H22B	120.1 (15)	N3X—C32X—H4XC	109.5
H21B—N21B—H22B	119 (2)	H4XA—C32X—H4XC	109.5
C2B—N3B—C4B	117.82 (14)	H4XB—C32X—H4XC	109.5
N41B—C4B—N3B	116.93 (15)	N3X'—C32X—H4XD	109.5
N41B—C4B—C5B	121.10 (16)	N3X'—C32X—H4XE	109.5
N3B—C4B—C5B	121.97 (15)	H4XD—C32X—H4XE	109.5
C4B—N41B—H41B	117.8 (15)	N3X'—C32X—H4XF	109.5
C4B—N41B—H42B	121.5 (14)	H4XD—C32X—H4XF	109.5
H41B—N41B—H42B	120 (2)	H4XE—C32X—H4XF	109.5
C6B—C5B—C4B	117.13 (16)	O21X—C2X—N3X	118.6 (3)
C6B—C5B—H5B	121.4	O21X—C2X—C1X	126.8 (3)
C4B—C5B—H5B	121.4	N3X—C2X—C1X	114.6 (3)
C5B—C6B—N1B	120.71 (15)	C2X—N3X—C32X	121.9 (3)
C5B—C6B—H6B	119.6	C2X—N3X—C31X	116.2 (3)
N1B—C6B—H6B	119.6	C32X—N3X—C31X	121.8 (2)
C2C—N1C—C6C	114.83 (15)	O21X—C2X'—N3X'	114.8 (5)
N3C—C2C—N1C	126.57 (15)	O21X—C2X'—C31X	133.9 (4)
N3C—C2C—N21C	116.44 (14)	N3X'—C2X'—C31X	111.2 (4)
N1C—C2C—N21C	116.95 (15)	C2X'—N3X'—C32X	116.7 (4)
C2C—N21C—H21C	116.9 (13)	C2X'—N3X'—C1X	113.1 (4)
C2C—N21C—H22C	114.6 (14)	C32X—N3X'—C1X	129.3 (3)
H21C—N21C—H22C	118 (2)

C6A—N1A—C2A—N3A	−0.1 (2)	N3B—C4B—C5B—C6B	1.0 (3)
C6A—N1A—C2A—S21A	179.58 (11)	C4B—C5B—C6B—N1B	0.4 (3)
N1A—C2A—N3A—C4A	2.1 (2)	C2B—N1B—C6B—C5B	−0.6 (2)
S21A—C2A—N3A—C4A	−177.64 (11)	C6C—N1C—C2C—N3C	−1.7 (2)
C2A—N3A—C4A—O41A	176.63 (14)	C6C—N1C—C2C—N21C	−179.45 (14)
C2A—N3A—C4A—C5A	−3.2 (2)	N1C—C2C—N3C—C4C	2.6 (2)
O41A—C4A—C5A—C6A	−177.34 (15)	N21C—C2C—N3C—C4C	−179.60 (14)
N3A—C4A—C5A—C6A	2.5 (2)	C2C—N3C—C4C—N41C	179.46 (15)
C4A—C5A—C6A—N1A	−0.6 (2)	C2C—N3C—C4C—C5C	−1.5 (2)
C4A—C5A—C6A—C7A	179.44 (16)	N41C—C4C—C5C—C6C	178.75 (16)
C2A—N1A—C6A—C5A	−0.6 (2)	N3C—C4C—C5C—C6C	−0.2 (2)
C2A—N1A—C6A—C7A	179.39 (14)	C2C—N1C—C6C—C5C	−0.4 (2)
C5A—C6A—C7A—C8A	−7.5 (3)	C4C—C5C—C6C—N1C	1.2 (3)
N1A—C6A—C7A—C8A	172.48 (14)	O21X—C2X—N3X—C32X	173.6 (2)
C6A—C7A—C8A—C9A	179.29 (15)	C1X—C2X—N3X—C32X	−6.2 (3)
C6B—N1B—C2B—N21B	179.34 (16)	O21X—C2X—N3X—C31X	−2.4 (3)
C6B—N1B—C2B—N3B	−0.6 (2)	C1X—C2X—N3X—C31X	177.69 (19)
N21B—C2B—N3B—C4B	−178.04 (15)	O21X—C2X'—N3X'—C32X	−172.3 (3)
N1B—C2B—N3B—C4B	1.9 (2)	C31X—C2X'—N3X'—C32X	10.6 (5)
C2B—N3B—C4B—N41B	178.38 (15)	O21X—C2X'—N3X'—C1X	−2.4 (6)
C2B—N3B—C4B—C5B	−2.1 (2)	C31X—C2X'—N3X'—C1X	−179.6 (3)
N41B—C4B—C5B—C6B	−179.50 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N3C	0.88 (1)	2.09 (1)	2.9644 (18)	170 (2)
N1B—H1B···N3A	0.92 (2)	1.89 (2)	2.806 (2)	175 (2)
N21B—H21B···O41A	0.89 (2)	1.95 (2)	2.834 (2)	173 (2)
N21B—H22B···O21Xⁱ	0.85 (2)	2.17 (2)	2.965 (2)	157 (2)
N41B—H41B···N21Cⁱⁱ	0.88 (2)	2.25 (2)	3.092 (2)	161 (2)
N41B—H42B···O1Wⁱⁱⁱ	0.88 (2)	2.10 (2)	2.891 (2)	150 (2)
N21C—H21C···N1C^iv	0.87 (2)	2.16 (2)	3.017 (2)	169 (2)
N21C—H22C···S21A	0.88 (2)	2.63 (2)	3.5018 (16)	172 (2)
N41C—H41C···O41Aⁱ	0.87 (2)	2.31 (2)	3.1499 (19)	162 (2)
N41C—H42C···O21X	0.88 (2)	2.05 (2)	2.903 (2)	162 (2)
O1W—H11W···S21Aⁱ	0.85 (1)	2.48 (1)	3.2975 (15)	161 (2)
O1W—H12W···O41A	0.85 (1)	1.99 (1)	2.8189 (18)	166 (2)

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

(II) 6-Methoxymethyl-2-thiouracil–N,N-dimethylformamide (1/1) top

Crystal data top

C₆H₈N₂O₂S·C₃H₇NO	Z = 2
M_r = 245.30	F(000) = 260
Triclinic, P1	D_x = 1.354 Mg m⁻³
a = 7.2516 (16) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9841 (17) Å	Cell parameters from 13024 reflections
c = 10.736 (2) Å	θ = 3.4–26.0°
α = 109.275 (16)°	µ = 0.27 mm⁻¹
β = 109.132 (17)°	T = 173 K
γ = 97.283 (17)°	Block, colourless
V = 601.7 (2) Å³	0.42 × 0.28 × 0.21 mm

Data collection top

Stoe IPDS II two-circle diffractometer	2024 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.066
ω scans	θ_max = 25.6°, θ_min = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −8→8
T_min = 0.624, T_max = 1.000	k = −10→10
5137 measured reflections	l = −12→13
2227 independent reflections

Refinement top

Refinement on F²	2 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.068P)² + 0.1405P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2227 reflections	Δρ_max = 0.52 e Å⁻³
154 parameters	Δρ_min = −0.31 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.7425 (2)	0.46056 (17)	0.52577 (14)	0.0274 (3)
H1A	0.765 (3)	0.536 (2)	0.492 (2)	0.033*
C2A	0.6163 (2)	0.3111 (2)	0.43389 (17)	0.0267 (3)
S21A	0.50109 (6)	0.26165 (5)	0.25776 (4)	0.03182 (18)
N3A	0.5911 (2)	0.20246 (17)	0.49346 (15)	0.0311 (3)
H3A	0.512 (3)	0.105 (2)	0.436 (2)	0.037*
C4A	0.6812 (3)	0.2324 (2)	0.63817 (18)	0.0334 (4)
O41A	0.6490 (2)	0.12101 (16)	0.67850 (14)	0.0479 (4)
C5A	0.8103 (3)	0.3936 (2)	0.72892 (17)	0.0309 (4)
H5A	0.8756	0.4240	0.8295	0.037*
C6A	0.8385 (2)	0.50167 (19)	0.67072 (16)	0.0274 (4)
C7A	0.9776 (3)	0.6709 (2)	0.75269 (17)	0.0302 (4)
H7A1	1.0787	0.6852	0.7112	0.036*
H7A2	0.8992	0.7527	0.7465	0.036*
O8A	1.0757 (2)	0.69386 (15)	0.89669 (13)	0.0418 (4)
C9A	1.2028 (3)	0.8568 (2)	0.98193 (19)	0.0403 (4)
H9A1	1.3077	0.8766	0.9462	0.060*
H9A2	1.2665	0.8702	1.0822	0.060*
H9A3	1.1210	0.9350	0.9758	0.060*
C1X	0.7595 (3)	0.6581 (2)	0.29652 (19)	0.0353 (4)
H1X	0.7198	0.5441	0.2394	0.042*
O11X	0.7994 (2)	0.70015 (16)	0.42590 (14)	0.0429 (3)
N2X	0.7671 (2)	0.75817 (19)	0.23034 (17)	0.0378 (4)
C3X	0.8247 (4)	0.9337 (3)	0.3069 (3)	0.0540 (6)
H3X1	0.8283	0.9605	0.4040	0.081*
H3X2	0.7260	0.9803	0.2558	0.081*
H3X3	0.9590	0.9791	0.3127	0.081*
C4X	0.7260 (4)	0.6968 (3)	0.0781 (2)	0.0556 (6)
H4X1	0.6986	0.5774	0.0394	0.083*
H4X2	0.8437	0.7436	0.0643	0.083*
H4X3	0.6080	0.7281	0.0279	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0345 (7)	0.0258 (7)	0.0221 (7)	0.0057 (6)	0.0091 (6)	0.0128 (6)
C2A	0.0312 (8)	0.0285 (8)	0.0215 (8)	0.0076 (6)	0.0104 (6)	0.0115 (6)
S21A	0.0396 (3)	0.0336 (3)	0.0191 (2)	0.00593 (19)	0.0069 (2)	0.01265 (19)
N3A	0.0417 (8)	0.0256 (7)	0.0207 (7)	0.0011 (6)	0.0085 (6)	0.0096 (6)
C4A	0.0438 (10)	0.0318 (9)	0.0224 (8)	0.0047 (7)	0.0098 (7)	0.0132 (7)
O41A	0.0742 (10)	0.0327 (7)	0.0248 (6)	−0.0055 (6)	0.0081 (6)	0.0157 (5)
C5A	0.0389 (9)	0.0295 (9)	0.0208 (8)	0.0050 (7)	0.0075 (7)	0.0114 (7)
C6A	0.0305 (8)	0.0285 (8)	0.0221 (8)	0.0077 (7)	0.0089 (7)	0.0105 (7)
C7A	0.0360 (9)	0.0291 (8)	0.0235 (8)	0.0042 (7)	0.0090 (7)	0.0125 (7)
O8A	0.0569 (8)	0.0333 (7)	0.0204 (6)	−0.0060 (6)	0.0043 (6)	0.0103 (5)
C9A	0.0495 (11)	0.0341 (9)	0.0249 (8)	−0.0018 (8)	0.0093 (8)	0.0067 (7)
C1X	0.0447 (10)	0.0331 (9)	0.0332 (9)	0.0115 (7)	0.0150 (8)	0.0191 (8)
O11X	0.0650 (9)	0.0359 (7)	0.0300 (7)	0.0104 (6)	0.0156 (6)	0.0197 (6)
N2X	0.0498 (9)	0.0387 (8)	0.0322 (8)	0.0144 (7)	0.0144 (7)	0.0234 (7)
C3X	0.0773 (16)	0.0379 (11)	0.0534 (13)	0.0170 (10)	0.0215 (11)	0.0295 (10)
C4X	0.0765 (16)	0.0655 (14)	0.0344 (11)	0.0209 (12)	0.0228 (11)	0.0299 (11)

Geometric parameters (Å, º) top

N1A—C2A	1.355 (2)	O8A—C9A	1.432 (2)
N1A—C6A	1.374 (2)	C9A—H9A1	0.9800
N1A—H1A	0.892 (15)	C9A—H9A2	0.9800
C2A—N3A	1.356 (2)	C9A—H9A3	0.9800
C2A—S21A	1.6695 (16)	C1X—O11X	1.232 (2)
N3A—C4A	1.388 (2)	C1X—N2X	1.324 (2)
N3A—H3A	0.873 (16)	C1X—H1X	0.9500
C4A—O41A	1.239 (2)	N2X—C3X	1.445 (3)
C4A—C5A	1.432 (2)	N2X—C4X	1.452 (2)
C5A—C6A	1.345 (2)	C3X—H3X1	0.9800
C5A—H5A	0.9500	C3X—H3X2	0.9800
C6A—C7A	1.500 (2)	C3X—H3X3	0.9800
C7A—O8A	1.4037 (19)	C4X—H4X1	0.9800
C7A—H7A1	0.9900	C4X—H4X2	0.9800
C7A—H7A2	0.9900	C4X—H4X3	0.9800

C2A—N1A—C6A	122.65 (14)	O8A—C9A—H9A1	109.5
C2A—N1A—H1A	119.5 (13)	O8A—C9A—H9A2	109.5
C6A—N1A—H1A	117.8 (13)	H9A1—C9A—H9A2	109.5
N1A—C2A—N3A	115.86 (14)	O8A—C9A—H9A3	109.5
N1A—C2A—S21A	122.40 (12)	H9A1—C9A—H9A3	109.5
N3A—C2A—S21A	121.74 (13)	H9A2—C9A—H9A3	109.5
C2A—N3A—C4A	125.72 (15)	O11X—C1X—N2X	125.54 (17)
C2A—N3A—H3A	117.8 (14)	O11X—C1X—H1X	117.2
C4A—N3A—H3A	116.5 (14)	N2X—C1X—H1X	117.2
O41A—C4A—N3A	119.34 (16)	C1X—N2X—C3X	121.77 (17)
O41A—C4A—C5A	125.40 (16)	C1X—N2X—C4X	121.46 (17)
N3A—C4A—C5A	115.25 (14)	C3X—N2X—C4X	116.72 (17)
C6A—C5A—C4A	119.53 (15)	N2X—C3X—H3X1	109.5
C6A—C5A—H5A	120.2	N2X—C3X—H3X2	109.5
C4A—C5A—H5A	120.2	H3X1—C3X—H3X2	109.5
C5A—C6A—N1A	120.98 (15)	N2X—C3X—H3X3	109.5
C5A—C6A—C7A	124.70 (15)	H3X1—C3X—H3X3	109.5
N1A—C6A—C7A	114.29 (14)	H3X2—C3X—H3X3	109.5
O8A—C7A—C6A	108.71 (13)	N2X—C4X—H4X1	109.5
O8A—C7A—H7A1	109.9	N2X—C4X—H4X2	109.5
C6A—C7A—H7A1	109.9	H4X1—C4X—H4X2	109.5
O8A—C7A—H7A2	109.9	N2X—C4X—H4X3	109.5
C6A—C7A—H7A2	109.9	H4X1—C4X—H4X3	109.5
H7A1—C7A—H7A2	108.3	H4X2—C4X—H4X3	109.5
C7A—O8A—C9A	111.19 (13)

C6A—N1A—C2A—N3A	−0.6 (2)	C4A—C5A—C6A—C7A	−176.78 (16)
C6A—N1A—C2A—S21A	−179.70 (12)	C2A—N1A—C6A—C5A	−0.3 (3)
N1A—C2A—N3A—C4A	0.6 (3)	C2A—N1A—C6A—C7A	177.82 (14)
S21A—C2A—N3A—C4A	179.71 (14)	C5A—C6A—C7A—O8A	1.9 (2)
C2A—N3A—C4A—O41A	−178.41 (17)	N1A—C6A—C7A—O8A	−176.14 (14)
C2A—N3A—C4A—C5A	0.2 (3)	C6A—C7A—O8A—C9A	−176.91 (14)
O41A—C4A—C5A—C6A	177.48 (18)	O11X—C1X—N2X—C3X	−0.3 (3)
N3A—C4A—C5A—C6A	−1.1 (3)	O11X—C1X—N2X—C4X	177.15 (19)
C4A—C5A—C6A—N1A	1.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O11X	0.89 (2)	1.86 (2)	2.7462 (19)	176 (2)
N3A—H3A···O41Aⁱ	0.87 (2)	1.95 (2)	2.820 (2)	175 (2)

Symmetry code: (i) −x+1, −y, −z+1.

(III) 6-Methoxymethyl-2-thiouracil–N,N-dimethylacetamide (1/1) top

Crystal data top

C₆H₈N₂O₂S·C₄H₉NO	Z = 2
M_r = 259.32	F(000) = 276
Triclinic, P1	D_x = 1.344 Mg m⁻³
a = 8.2090 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1804 (17) Å	Cell parameters from 5511 reflections
c = 9.5617 (17) Å	θ = 3.2–26.3°
α = 65.128 (14)°	µ = 0.25 mm⁻¹
β = 83.198 (15)°	T = 173 K
γ = 78.854 (14)°	Plate, colourless
V = 640.9 (2) Å³	0.23 × 0.10 × 0.08 mm

Data collection top

Stoe IPDS II two-circle diffractometer	1840 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.031
ω scans	θ_max = 25.9°, θ_min = 3.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→10
T_min = 0.409, T_max = 1.000	k = −11→10
5010 measured reflections	l = −10→11
2436 independent reflections

Refinement top

Refinement on F²	22 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.035	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.079	w = 1/[σ²(F_o²) + (0.0416P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max = 0.001
2436 reflections	Δρ_max = 0.23 e Å⁻³
183 parameters	Δρ_min = −0.18 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.77783 (18)	0.41167 (16)	0.13885 (18)	0.0239 (3)
H1A	0.849 (2)	0.359 (2)	0.103 (2)	0.029*
C2A	0.7597 (2)	0.35147 (19)	0.2938 (2)	0.0244 (4)
S21A	0.87409 (6)	0.18067 (5)	0.40823 (6)	0.03405 (15)
N3A	0.64058 (18)	0.44049 (17)	0.35064 (19)	0.0259 (3)
H3A	0.626 (2)	0.408 (2)	0.444 (3)	0.031*
C4A	0.5354 (2)	0.57888 (19)	0.2636 (2)	0.0292 (4)
O41A	0.42760 (18)	0.64592 (16)	0.32888 (16)	0.0434 (4)
C5A	0.5628 (2)	0.63325 (19)	0.1014 (2)	0.0281 (4)
H5A	0.4963	0.7287	0.0344	0.034*
C6A	0.6827 (2)	0.54994 (19)	0.0422 (2)	0.0251 (4)
C7A	0.7243 (2)	0.5993 (2)	−0.1257 (2)	0.0279 (4)
H7A1	0.8303	0.6431	−0.1531	0.033*
H7A2	0.7372	0.5040	−0.1518	0.033*
O8A	0.59492 (15)	0.71896 (14)	−0.20872 (15)	0.0331 (3)
C9A	0.6363 (3)	0.7874 (2)	−0.3684 (2)	0.0427 (5)
H9A1	0.7281	0.8484	−0.3873	0.064*
H9A2	0.5394	0.8608	−0.4239	0.064*
H9A3	0.6701	0.7004	−0.4047	0.064*
C1X	1.1881 (3)	0.0361 (2)	0.1016 (3)	0.0470 (6)
H1XA	1.3012	0.0564	0.1011	0.071*	0.833 (6)
H1XB	1.1931	−0.0703	0.0992	0.071*	0.833 (6)
H1XC	1.1264	0.0374	0.1954	0.071*	0.833 (6)
H1XD	1.2678	−0.0650	0.1415	0.071*	0.167 (6)
H1XE	1.2252	0.1197	0.1230	0.071*	0.167 (6)
H1XF	1.0785	0.0167	0.1520	0.071*	0.167 (6)
O21X	0.98693 (17)	0.27546 (16)	−0.03148 (17)	0.0423 (4)
C31X	1.0673 (3)	0.2913 (3)	−0.3094 (3)	0.0551 (6)
H3XA	1.0260	0.2407	−0.3674	0.083*	0.833 (6)
H3XB	1.1461	0.3623	−0.3753	0.083*	0.833 (6)
H3XC	0.9739	0.3558	−0.2767	0.083*	0.833 (6)
H3XD	1.1543	0.2211	−0.3419	0.083*	0.167 (6)
H3XE	0.9589	0.2856	−0.3385	0.083*	0.167 (6)
H3XF	1.0887	0.4038	−0.3601	0.083*	0.167 (6)
C32X	1.2881 (3)	0.0434 (3)	−0.1921 (3)	0.0528 (6)
H4XA	1.3167	−0.0460	−0.0922	0.079*	0.833 (6)
H4XB	1.3855	0.0965	−0.2395	0.079*	0.833 (6)
H4XC	1.2531	0.0005	−0.2598	0.079*	0.833 (6)
H4XE	1.3616	−0.0586	−0.1370	0.079*	0.167 (6)
H4XD	1.2192	0.0276	−0.2599	0.079*	0.167 (6)
H4XF	1.3552	0.1282	−0.2541	0.079*	0.167 (6)
C2X	1.1030 (3)	0.1645 (3)	−0.0358 (3)	0.0319 (7)	0.833 (6)
N3X	1.1533 (3)	0.1611 (3)	−0.1696 (3)	0.0378 (7)	0.833 (6)
C2X'	1.0672 (10)	0.2353 (9)	−0.1356 (8)	0.018 (3)	0.167 (6)
N3X'	1.1769 (10)	0.0948 (10)	−0.0762 (8)	0.025 (3)	0.167 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0224 (7)	0.0270 (7)	0.0213 (8)	0.0005 (5)	0.0005 (6)	−0.0112 (6)
C2A	0.0218 (8)	0.0261 (8)	0.0278 (11)	−0.0048 (6)	−0.0013 (7)	−0.0130 (7)
S21A	0.0353 (3)	0.0313 (2)	0.0295 (3)	0.00720 (18)	−0.0077 (2)	−0.01033 (19)
N3A	0.0303 (8)	0.0270 (7)	0.0181 (8)	−0.0004 (6)	−0.0002 (6)	−0.0089 (6)
C4A	0.0298 (10)	0.0272 (8)	0.0280 (11)	−0.0003 (7)	0.0009 (8)	−0.0112 (8)
O41A	0.0502 (8)	0.0415 (7)	0.0271 (8)	0.0160 (6)	0.0026 (6)	−0.0139 (6)
C5A	0.0306 (9)	0.0245 (8)	0.0234 (10)	0.0003 (7)	−0.0011 (7)	−0.0061 (7)
C6A	0.0234 (9)	0.0263 (8)	0.0250 (10)	−0.0072 (6)	−0.0010 (7)	−0.0086 (7)
C7A	0.0245 (9)	0.0327 (9)	0.0226 (10)	−0.0033 (7)	0.0025 (7)	−0.0090 (8)
O8A	0.0317 (7)	0.0357 (6)	0.0209 (7)	−0.0005 (5)	0.0004 (5)	−0.0033 (5)
C9A	0.0457 (12)	0.0462 (11)	0.0241 (11)	−0.0114 (9)	0.0021 (9)	−0.0018 (9)
C1X	0.0447 (12)	0.0391 (10)	0.0466 (14)	−0.0102 (9)	−0.0145 (10)	−0.0025 (10)
O21X	0.0398 (8)	0.0487 (8)	0.0400 (9)	0.0098 (6)	−0.0006 (6)	−0.0271 (7)
C31X	0.0605 (15)	0.0771 (16)	0.0286 (13)	−0.0235 (12)	−0.0030 (11)	−0.0167 (12)
C32X	0.0488 (13)	0.0545 (12)	0.0628 (17)	0.0030 (10)	0.0088 (11)	−0.0388 (12)
C2X	0.0295 (13)	0.0361 (14)	0.0346 (17)	−0.0081 (11)	−0.0007 (11)	−0.0177 (13)
N3X	0.0339 (13)	0.0477 (14)	0.0425 (17)	−0.0057 (11)	0.0044 (11)	−0.0305 (13)
C2X'	0.018 (5)	0.018 (5)	0.019 (7)	−0.003 (4)	0.000 (4)	−0.008 (5)
N3X'	0.027 (5)	0.025 (5)	0.024 (6)	0.010 (4)	−0.003 (5)	−0.017 (5)

Geometric parameters (Å, º) top

N1A—C2A	1.347 (2)	C1X—H1XD	0.9800
N1A—C6A	1.370 (2)	C1X—H1XE	0.9800
N1A—H1A	0.82 (2)	C1X—H1XF	0.9800
C2A—N3A	1.363 (2)	O21X—C2X	1.264 (3)
C2A—S21A	1.6639 (17)	O21X—C2X'	1.273 (6)
N3A—C4A	1.381 (2)	C31X—N3X	1.506 (3)
N3A—H3A	0.82 (2)	C31X—C2X'	1.519 (7)
C4A—O41A	1.238 (2)	C31X—H3XA	0.9800
C4A—C5A	1.419 (3)	C31X—H3XB	0.9800
C5A—C6A	1.348 (2)	C31X—H3XC	0.9800
C5A—H5A	0.9500	C31X—H3XD	0.9799
C6A—C7A	1.489 (3)	C31X—H3XE	0.9799
C7A—O8A	1.407 (2)	C31X—H3XF	0.9800
C7A—H7A1	0.9900	C32X—N3X	1.455 (3)
C7A—H7A2	0.9900	C32X—N3X'	1.523 (6)
O8A—C9A	1.412 (2)	C32X—H4XA	0.9800
C9A—H9A1	0.9800	C32X—H4XB	0.9800
C9A—H9A2	0.9800	C32X—H4XC	0.9800
C9A—H9A3	0.9800	C32X—H4XE	0.9800
C1X—C2X	1.484 (3)	C32X—H4XD	0.9800
C1X—N3X'	1.561 (7)	C32X—H4XF	0.9800
C1X—H1XA	0.9800	C2X—N3X	1.308 (4)
C1X—H1XB	0.9800	C2X'—N3X'	1.361 (8)
C1X—H1XC	0.9800

C2A—N1A—C6A	123.67 (14)	N3X'—C1X—H1XF	109.5
C2A—N1A—H1A	116.1 (14)	H1XD—C1X—H1XF	109.5
C6A—N1A—H1A	120.2 (14)	H1XE—C1X—H1XF	109.5
N1A—C2A—N3A	115.21 (15)	N3X—C31X—H3XA	109.5
N1A—C2A—S21A	122.58 (12)	N3X—C31X—H3XB	109.5
N3A—C2A—S21A	122.21 (14)	H3XA—C31X—H3XB	109.5
C2A—N3A—C4A	125.69 (16)	N3X—C31X—H3XC	109.5
C2A—N3A—H3A	118.1 (13)	H3XA—C31X—H3XC	109.5
C4A—N3A—H3A	116.2 (13)	H3XB—C31X—H3XC	109.5
O41A—C4A—N3A	119.71 (17)	C2X'—C31X—H3XD	109.6
O41A—C4A—C5A	125.05 (15)	C2X'—C31X—H3XE	109.5
N3A—C4A—C5A	115.24 (15)	H3XD—C31X—H3XE	109.5
C6A—C5A—C4A	120.24 (16)	C2X'—C31X—H3XF	109.3
C6A—C5A—H5A	119.9	H3XD—C31X—H3XF	109.5
C4A—C5A—H5A	119.9	H3XE—C31X—H3XF	109.5
C5A—C6A—N1A	119.88 (17)	N3X—C32X—H4XA	109.5
C5A—C6A—C7A	124.37 (15)	N3X—C32X—H4XB	109.5
N1A—C6A—C7A	115.74 (14)	H4XA—C32X—H4XB	109.5
O8A—C7A—C6A	108.52 (13)	N3X—C32X—H4XC	109.5
O8A—C7A—H7A1	110.0	H4XA—C32X—H4XC	109.5
C6A—C7A—H7A1	110.0	H4XB—C32X—H4XC	109.5
O8A—C7A—H7A2	110.0	N3X'—C32X—H4XE	109.5
C6A—C7A—H7A2	110.0	N3X'—C32X—H4XD	109.5
H7A1—C7A—H7A2	108.4	H4XE—C32X—H4XD	109.5
C7A—O8A—C9A	111.53 (13)	N3X'—C32X—H4XF	109.5
O8A—C9A—H9A1	109.5	H4XE—C32X—H4XF	109.5
O8A—C9A—H9A2	109.5	H4XD—C32X—H4XF	109.5
H9A1—C9A—H9A2	109.5	O21X—C2X—N3X	118.7 (3)
O8A—C9A—H9A3	109.5	O21X—C2X—C1X	124.4 (2)
H9A1—C9A—H9A3	109.5	N3X—C2X—C1X	116.9 (2)
H9A2—C9A—H9A3	109.5	C2X—N3X—C32X	124.6 (3)
C2X—C1X—H1XA	109.5	C2X—N3X—C31X	117.1 (2)
C2X—C1X—H1XB	109.5	C32X—N3X—C31X	118.3 (2)
H1XA—C1X—H1XB	109.5	O21X—C2X'—N3X'	112.6 (6)
C2X—C1X—H1XC	109.5	O21X—C2X'—C31X	138.3 (6)
H1XA—C1X—H1XC	109.5	N3X'—C2X'—C31X	108.9 (5)
H1XB—C1X—H1XC	109.5	C2X'—N3X'—C32X	116.4 (6)
N3X'—C1X—H1XD	109.5	C2X'—N3X'—C1X	111.1 (5)
N3X'—C1X—H1XE	109.5	C32X—N3X'—C1X	131.2 (5)
H1XD—C1X—H1XE	109.5

C6A—N1A—C2A—N3A	−1.5 (2)	C5A—C6A—C7A—O8A	−14.3 (2)
C6A—N1A—C2A—S21A	178.47 (13)	N1A—C6A—C7A—O8A	167.01 (14)
N1A—C2A—N3A—C4A	3.2 (2)	C6A—C7A—O8A—C9A	171.95 (15)
S21A—C2A—N3A—C4A	−176.77 (15)	O21X—C2X—N3X—C32X	178.3 (2)
C2A—N3A—C4A—O41A	177.25 (17)	C1X—C2X—N3X—C32X	−1.6 (3)
C2A—N3A—C4A—C5A	−3.0 (3)	O21X—C2X—N3X—C31X	−0.1 (3)
O41A—C4A—C5A—C6A	−179.24 (18)	C1X—C2X—N3X—C31X	−179.93 (19)
N3A—C4A—C5A—C6A	1.0 (3)	O21X—C2X'—N3X'—C32X	−175.6 (6)
C4A—C5A—C6A—N1A	0.4 (3)	C31X—C2X'—N3X'—C32X	9.0 (10)
C4A—C5A—C6A—C7A	−178.22 (17)	O21X—C2X'—N3X'—C1X	−7.3 (11)
C2A—N1A—C6A—C5A	−0.2 (3)	C31X—C2X'—N3X'—C1X	177.2 (5)
C2A—N1A—C6A—C7A	178.58 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21X	0.82 (2)	1.92 (2)	2.717 (2)	164 (2)
N3A—H3A···O41Aⁱ	0.82 (2)	2.03 (2)	2.838 (2)	173.0 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

(IV) 6-Methoxymethyl-2-thiouracil–dimethyl sulfoxide (1/1) top

Crystal data top

C₆H₈N₂O₂S·C₂H₆OS	F(000) = 528
M_r = 250.33	D_x = 1.385 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1891 (7) Å	Cell parameters from 9266 reflections
b = 17.7131 (13) Å	θ = 3.4–26.2°
c = 8.3032 (8) Å	µ = 0.43 mm⁻¹
β = 94.643 (8)°	T = 173 K
V = 1200.46 (18) Å³	Plate, colourless
Z = 4	0.25 × 0.23 × 0.05 mm

Data collection top

Stoe IPDS II two-circle diffractometer	1908 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.076
ω scans	θ_max = 25.8°, θ_min = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→10
T_min = 0.355, T_max = 1.000	k = −18→21
9943 measured reflections	l = −10→10
2304 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.087	w = 1/[σ²(F_o²) + (0.0463P)²] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2304 reflections	Δρ_max = 0.24 e Å⁻³
145 parameters	Δρ_min = −0.23 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.38163 (18)	0.29077 (9)	0.29629 (19)	0.0211 (3)
H1A	0.322 (3)	0.2592 (14)	0.240 (3)	0.025*
C2A	0.3421 (2)	0.36449 (12)	0.2892 (2)	0.0226 (4)
S21A	0.18079 (6)	0.39693 (3)	0.17256 (6)	0.03033 (15)
N3A	0.44147 (18)	0.41119 (10)	0.38232 (19)	0.0227 (3)
H3A	0.408 (3)	0.4559 (15)	0.389 (3)	0.027*
C4A	0.5747 (2)	0.38916 (11)	0.4850 (2)	0.0241 (4)
O41A	0.65283 (17)	0.43686 (8)	0.56769 (19)	0.0333 (4)
C5A	0.6066 (2)	0.31025 (11)	0.4876 (2)	0.0241 (4)
H5A	0.6980	0.2909	0.5524	0.029*
C6A	0.5074 (2)	0.26294 (11)	0.3982 (2)	0.0211 (4)
C7A	0.5209 (2)	0.17921 (11)	0.4063 (2)	0.0242 (4)
H7A1	0.4188	0.1573	0.4424	0.029*
H7A2	0.5381	0.1586	0.2981	0.029*
O8A	0.65454 (17)	0.16055 (8)	0.5164 (2)	0.0342 (4)
C9A	0.6807 (3)	0.08162 (13)	0.5286 (3)	0.0418 (6)
H9A1	0.5834	0.0574	0.5668	0.063*
H9A2	0.7756	0.0716	0.6052	0.063*
H9A3	0.7011	0.0613	0.4223	0.063*
C1X	−0.0230 (2)	0.19779 (15)	0.2874 (3)	0.0385 (5)
H1X1	0.0547	0.1905	0.3823	0.058*
H1X2	−0.1285	0.1750	0.3074	0.058*
H1X3	−0.0379	0.2519	0.2669	0.058*
S2X	0.05480 (5)	0.15411 (3)	0.11607 (6)	0.02723 (15)
O21X	0.22723 (16)	0.18299 (9)	0.11312 (18)	0.0323 (4)
C3X	0.0753 (3)	0.06106 (15)	0.1922 (4)	0.0482 (6)
H3X1	0.1316	0.0298	0.1165	0.072*
H3X2	−0.0335	0.0400	0.2051	0.072*
H3X3	0.1393	0.0618	0.2972	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0231 (7)	0.0189 (9)	0.0215 (8)	−0.0019 (6)	0.0019 (6)	−0.0041 (7)
C2A	0.0244 (8)	0.0234 (10)	0.0205 (9)	−0.0030 (7)	0.0042 (7)	−0.0009 (8)
S21A	0.0314 (3)	0.0255 (3)	0.0324 (3)	0.0037 (2)	−0.00794 (19)	−0.0018 (2)
N3A	0.0258 (7)	0.0161 (8)	0.0259 (8)	0.0000 (6)	0.0006 (6)	−0.0016 (7)
C4A	0.0244 (8)	0.0229 (11)	0.0249 (9)	−0.0021 (7)	0.0011 (7)	−0.0019 (8)
O41A	0.0332 (7)	0.0220 (8)	0.0425 (9)	−0.0023 (6)	−0.0102 (6)	−0.0064 (7)
C5A	0.0231 (8)	0.0221 (10)	0.0270 (10)	0.0010 (7)	0.0003 (7)	−0.0019 (8)
C6A	0.0208 (8)	0.0221 (10)	0.0213 (9)	0.0004 (7)	0.0062 (6)	−0.0019 (8)
C7A	0.0266 (9)	0.0209 (11)	0.0253 (9)	0.0000 (7)	0.0041 (7)	−0.0005 (8)
O8A	0.0341 (7)	0.0206 (8)	0.0466 (9)	0.0053 (6)	−0.0057 (6)	0.0025 (7)
C9A	0.0479 (12)	0.0222 (12)	0.0557 (15)	0.0103 (9)	0.0061 (10)	0.0063 (11)
C1X	0.0306 (10)	0.0524 (16)	0.0333 (11)	0.0049 (9)	0.0079 (8)	0.0025 (11)
S2X	0.0241 (2)	0.0312 (3)	0.0260 (3)	−0.00505 (19)	−0.00019 (17)	0.0006 (2)
O21X	0.0288 (7)	0.0334 (9)	0.0361 (8)	−0.0107 (6)	0.0111 (6)	−0.0122 (7)
C3X	0.0475 (13)	0.0310 (14)	0.0657 (17)	−0.0102 (11)	0.0025 (11)	0.0066 (12)

Geometric parameters (Å, º) top

N1A—C2A	1.345 (3)	C7A—H7A2	0.9900
N1A—C6A	1.371 (2)	O8A—C9A	1.417 (3)
N1A—H1A	0.85 (2)	C9A—H9A1	0.9800
C2A—N3A	1.357 (2)	C9A—H9A2	0.9800
C2A—S21A	1.6750 (18)	C9A—H9A3	0.9800
N3A—C4A	1.385 (2)	C1X—S2X	1.782 (2)
N3A—H3A	0.84 (3)	C1X—H1X1	0.9800
C4A—O41A	1.234 (2)	C1X—H1X2	0.9800
C4A—C5A	1.422 (3)	C1X—H1X3	0.9800
C5A—C6A	1.347 (3)	S2X—O21X	1.5039 (13)
C5A—H5A	0.9500	S2X—C3X	1.769 (3)
C6A—C7A	1.488 (3)	C3X—H3X1	0.9800
C7A—O8A	1.407 (2)	C3X—H3X2	0.9800
C7A—H7A1	0.9900	C3X—H3X3	0.9800

C2A—N1A—C6A	122.83 (16)	H7A1—C7A—H7A2	108.4
C2A—N1A—H1A	119.1 (15)	C7A—O8A—C9A	112.54 (17)
C6A—N1A—H1A	118.0 (15)	O8A—C9A—H9A1	109.5
N1A—C2A—N3A	115.82 (16)	O8A—C9A—H9A2	109.5
N1A—C2A—S21A	122.27 (14)	H9A1—C9A—H9A2	109.5
N3A—C2A—S21A	121.91 (16)	O8A—C9A—H9A3	109.5
C2A—N3A—C4A	125.79 (18)	H9A1—C9A—H9A3	109.5
C2A—N3A—H3A	115.5 (16)	H9A2—C9A—H9A3	109.5
C4A—N3A—H3A	117.8 (16)	S2X—C1X—H1X1	109.5
O41A—C4A—N3A	119.77 (18)	S2X—C1X—H1X2	109.5
O41A—C4A—C5A	125.31 (18)	H1X1—C1X—H1X2	109.5
N3A—C4A—C5A	114.89 (17)	S2X—C1X—H1X3	109.5
C6A—C5A—C4A	120.08 (18)	H1X1—C1X—H1X3	109.5
C6A—C5A—H5A	120.0	H1X2—C1X—H1X3	109.5
C4A—C5A—H5A	120.0	O21X—S2X—C3X	105.10 (10)
C5A—C6A—N1A	120.38 (18)	O21X—S2X—C1X	105.20 (10)
C5A—C6A—C7A	123.76 (18)	C3X—S2X—C1X	98.57 (13)
N1A—C6A—C7A	115.82 (16)	S2X—C3X—H3X1	109.5
O8A—C7A—C6A	108.32 (16)	S2X—C3X—H3X2	109.5
O8A—C7A—H7A1	110.0	H3X1—C3X—H3X2	109.5
C6A—C7A—H7A1	110.0	S2X—C3X—H3X3	109.5
O8A—C7A—H7A2	110.0	H3X1—C3X—H3X3	109.5
C6A—C7A—H7A2	110.0	H3X2—C3X—H3X3	109.5

C6A—N1A—C2A—N3A	4.1 (2)	C4A—C5A—C6A—N1A	4.3 (3)
C6A—N1A—C2A—S21A	−176.06 (13)	C4A—C5A—C6A—C7A	−173.43 (17)
N1A—C2A—N3A—C4A	−1.8 (3)	C2A—N1A—C6A—C5A	−5.5 (3)
S21A—C2A—N3A—C4A	178.36 (15)	C2A—N1A—C6A—C7A	172.38 (16)
C2A—N3A—C4A—O41A	−177.66 (17)	C5A—C6A—C7A—O8A	−1.8 (2)
C2A—N3A—C4A—C5A	0.8 (3)	N1A—C6A—C7A—O8A	−179.58 (15)
O41A—C4A—C5A—C6A	176.36 (19)	C6A—C7A—O8A—C9A	−178.12 (17)
N3A—C4A—C5A—C6A	−2.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21X	0.85 (2)	1.85 (2)	2.692 (2)	170 (2)
N3A—H3A···O41Aⁱ	0.84 (3)	2.00 (3)	2.840 (2)	173 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

(V) 6-Methoxymethyl-2-thiouracil–1-methylpyrrolidin-2-one (1/1) top

Crystal data top

C₆H₈N₂O₂S·C₅H₉NO	Z = 2
M_r = 271.33	F(000) = 288
Triclinic, P1	D_x = 1.392 Mg m⁻³
a = 6.7673 (13) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9189 (15) Å	Cell parameters from 11541 reflections
c = 10.4097 (17) Å	θ = 3.4–26.2°
α = 82.868 (13)°	µ = 0.26 mm⁻¹
β = 74.093 (13)°	T = 173 K
γ = 74.741 (13)°	Plate, colourless
V = 647.3 (2) Å³	0.46 × 0.32 × 0.21 mm

Data collection top

Stoe IPDS II two-circle diffractometer	2201 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.042
ω scans	θ_max = 25.8°, θ_min = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −8→8
T_min = 0.320, T_max = 1.000	k = −11→12
5425 measured reflections	l = −12→12
2463 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.112	w = 1/[σ²(F_o²) + (0.0635P)² + 0.1726P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
2463 reflections	Δρ_max = 0.35 e Å⁻³
171 parameters	Δρ_min = −0.24 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.2166 (2)	0.61812 (15)	0.44620 (15)	0.0274 (3)
H1A	0.212 (3)	0.560 (2)	0.508 (2)	0.033*
C2A	0.1376 (3)	0.75446 (17)	0.47248 (17)	0.0261 (4)
S21A	0.03886 (8)	0.80756 (4)	0.62876 (4)	0.03244 (17)
N3A	0.1445 (2)	0.84523 (15)	0.36394 (14)	0.0286 (3)
H3A	0.093 (3)	0.934 (2)	0.380 (2)	0.034*
C4A	0.2241 (3)	0.81094 (18)	0.22971 (17)	0.0302 (4)
O41A	0.2211 (2)	0.90486 (14)	0.14224 (13)	0.0408 (4)
C5A	0.3028 (3)	0.66335 (18)	0.21180 (17)	0.0294 (4)
H5A	0.3581	0.6302	0.1242	0.035*
C6A	0.2983 (3)	0.57248 (18)	0.31858 (17)	0.0269 (4)
C7A	0.3780 (3)	0.41709 (18)	0.31069 (16)	0.0312 (4)
H7A1	0.4961	0.3834	0.3545	0.037*
H7A2	0.2632	0.3706	0.3579	0.037*
O8A	0.4480 (2)	0.38354 (13)	0.17585 (12)	0.0371 (3)
C9A	0.5266 (3)	0.23571 (18)	0.16689 (18)	0.0370 (4)
H9A1	0.6479	0.2040	0.2066	0.056*
H9A2	0.5711	0.2129	0.0727	0.056*
H9A3	0.4149	0.1888	0.2152	0.056*
N1X	0.2742 (3)	0.19225 (16)	0.75295 (15)	0.0340 (4)
C11X	0.3703 (4)	0.0967 (2)	0.6468 (2)	0.0426 (5)
H11A	0.3841	0.1497	0.5601	0.064*
H11B	0.2813	0.0315	0.6523	0.064*
H11C	0.5107	0.0441	0.6559	0.064*
C2X	0.2251 (3)	0.33122 (19)	0.73198 (17)	0.0308 (4)
O21X	0.2520 (2)	0.39172 (13)	0.62024 (13)	0.0409 (4)
C3X	0.1354 (3)	0.3987 (2)	0.86378 (19)	0.0392 (4)
H3X1	−0.0037	0.4646	0.8663	0.047*
H3X2	0.2325	0.4500	0.8803	0.047*
C4X	0.1123 (4)	0.2760 (3)	0.9670 (2)	0.0541 (6)
H4X1	0.1707	0.2840	1.0424	0.065*
H4X2	−0.0386	0.2744	1.0027	0.065*
C5X	0.2356 (4)	0.1440 (2)	0.8940 (2)	0.0458 (5)
H5X1	0.3704	0.1040	0.9198	0.055*
H5X2	0.1516	0.0725	0.9133	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0355 (8)	0.0226 (7)	0.0223 (7)	−0.0054 (6)	−0.0081 (6)	0.0038 (6)
C2A	0.0275 (8)	0.0249 (8)	0.0258 (8)	−0.0066 (6)	−0.0075 (6)	0.0014 (6)
S21A	0.0461 (3)	0.0259 (2)	0.0222 (2)	−0.00665 (19)	−0.00590 (18)	−0.00027 (16)
N3A	0.0371 (8)	0.0223 (7)	0.0234 (7)	−0.0041 (6)	−0.0070 (6)	0.0017 (6)
C4A	0.0362 (9)	0.0280 (9)	0.0242 (8)	−0.0062 (7)	−0.0065 (7)	0.0014 (7)
O41A	0.0611 (9)	0.0272 (6)	0.0261 (6)	−0.0046 (6)	−0.0073 (6)	0.0069 (5)
C5A	0.0357 (9)	0.0269 (9)	0.0229 (8)	−0.0047 (7)	−0.0067 (7)	0.0002 (7)
C6A	0.0289 (8)	0.0260 (8)	0.0254 (8)	−0.0053 (7)	−0.0078 (6)	−0.0007 (6)
C7A	0.0440 (10)	0.0247 (8)	0.0220 (8)	−0.0061 (7)	−0.0073 (7)	0.0018 (6)
O8A	0.0589 (9)	0.0227 (6)	0.0231 (6)	−0.0031 (6)	−0.0064 (5)	−0.0002 (5)
C9A	0.0516 (12)	0.0250 (9)	0.0282 (9)	−0.0024 (8)	−0.0059 (8)	−0.0025 (7)
N1X	0.0424 (9)	0.0293 (8)	0.0294 (8)	−0.0091 (6)	−0.0116 (6)	0.0088 (6)
C11X	0.0496 (12)	0.0296 (10)	0.0483 (12)	−0.0071 (8)	−0.0143 (9)	−0.0018 (9)
C2X	0.0361 (9)	0.0287 (8)	0.0270 (9)	−0.0078 (7)	−0.0093 (7)	0.0039 (7)
O21X	0.0620 (9)	0.0276 (7)	0.0275 (6)	−0.0079 (6)	−0.0083 (6)	0.0071 (5)
C3X	0.0397 (11)	0.0477 (11)	0.0295 (9)	−0.0090 (9)	−0.0068 (8)	−0.0076 (8)
C4X	0.0558 (14)	0.0745 (16)	0.0259 (10)	−0.0112 (12)	−0.0101 (9)	0.0091 (10)
C5X	0.0492 (12)	0.0516 (12)	0.0356 (11)	−0.0169 (10)	−0.0152 (9)	0.0220 (9)

Geometric parameters (Å, º) top

N1A—C2A	1.349 (2)	C9A—H9A3	0.9800
N1A—C6A	1.375 (2)	N1X—C2X	1.335 (2)
N1A—H1A	0.81 (2)	N1X—C11X	1.443 (3)
C2A—N3A	1.353 (2)	N1X—C5X	1.461 (2)
C2A—S21A	1.6740 (17)	C11X—H11A	0.9800
N3A—C4A	1.403 (2)	C11X—H11B	0.9800
N3A—H3A	0.88 (2)	C11X—H11C	0.9800
C4A—O41A	1.219 (2)	C2X—O21X	1.231 (2)
C4A—C5A	1.437 (2)	C2X—C3X	1.502 (3)
C5A—C6A	1.340 (2)	C3X—C4X	1.531 (3)
C5A—H5A	0.9500	C3X—H3X1	0.9900
C6A—C7A	1.498 (2)	C3X—H3X2	0.9900
C7A—O8A	1.405 (2)	C4X—C5X	1.521 (3)
C7A—H7A1	0.9900	C4X—H4X1	0.9900
C7A—H7A2	0.9900	C4X—H4X2	0.9900
O8A—C9A	1.428 (2)	C5X—H5X1	0.9900
C9A—H9A1	0.9800	C5X—H5X2	0.9900
C9A—H9A2	0.9800

C2A—N1A—C6A	123.10 (15)	C2X—N1X—C11X	123.51 (15)
C2A—N1A—H1A	118.9 (15)	C2X—N1X—C5X	114.21 (16)
C6A—N1A—H1A	117.9 (15)	C11X—N1X—C5X	122.15 (16)
N1A—C2A—N3A	115.42 (15)	N1X—C11X—H11A	109.5
N1A—C2A—S21A	122.25 (13)	N1X—C11X—H11B	109.5
N3A—C2A—S21A	122.33 (13)	H11A—C11X—H11B	109.5
C2A—N3A—C4A	126.47 (15)	N1X—C11X—H11C	109.5
C2A—N3A—H3A	116.2 (14)	H11A—C11X—H11C	109.5
C4A—N3A—H3A	117.4 (14)	H11B—C11X—H11C	109.5
O41A—C4A—N3A	118.98 (16)	O21X—C2X—N1X	123.80 (17)
O41A—C4A—C5A	127.00 (16)	O21X—C2X—C3X	126.55 (17)
N3A—C4A—C5A	114.03 (15)	N1X—C2X—C3X	109.65 (15)
C6A—C5A—C4A	120.04 (16)	C2X—C3X—C4X	104.24 (17)
C6A—C5A—H5A	120.0	C2X—C3X—H3X1	110.9
C4A—C5A—H5A	120.0	C4X—C3X—H3X1	110.9
C5A—C6A—N1A	120.94 (16)	C2X—C3X—H3X2	110.9
C5A—C6A—C7A	124.18 (16)	C4X—C3X—H3X2	110.9
N1A—C6A—C7A	114.89 (15)	H3X1—C3X—H3X2	108.9
O8A—C7A—C6A	109.38 (14)	C5X—C4X—C3X	106.24 (16)
O8A—C7A—H7A1	109.8	C5X—C4X—H4X1	110.5
C6A—C7A—H7A1	109.8	C3X—C4X—H4X1	110.5
O8A—C7A—H7A2	109.8	C5X—C4X—H4X2	110.5
C6A—C7A—H7A2	109.8	C3X—C4X—H4X2	110.5
H7A1—C7A—H7A2	108.2	H4X1—C4X—H4X2	108.7
C7A—O8A—C9A	109.95 (13)	N1X—C5X—C4X	103.71 (16)
O8A—C9A—H9A1	109.5	N1X—C5X—H5X1	111.0
O8A—C9A—H9A2	109.5	C4X—C5X—H5X1	111.0
H9A1—C9A—H9A2	109.5	N1X—C5X—H5X2	111.0
O8A—C9A—H9A3	109.5	C4X—C5X—H5X2	111.0
H9A1—C9A—H9A3	109.5	H5X1—C5X—H5X2	109.0
H9A2—C9A—H9A3	109.5

C6A—N1A—C2A—N3A	−0.3 (2)	N1A—C6A—C7A—O8A	177.35 (15)
C6A—N1A—C2A—S21A	179.96 (13)	C6A—C7A—O8A—C9A	179.35 (15)
N1A—C2A—N3A—C4A	0.1 (3)	C11X—N1X—C2X—O21X	1.8 (3)
S21A—C2A—N3A—C4A	179.90 (14)	C5X—N1X—C2X—O21X	177.87 (19)
C2A—N3A—C4A—O41A	−179.44 (17)	C11X—N1X—C2X—C3X	−177.93 (18)
C2A—N3A—C4A—C5A	0.4 (3)	C5X—N1X—C2X—C3X	−1.9 (2)
O41A—C4A—C5A—C6A	178.98 (19)	O21X—C2X—C3X—C4X	173.2 (2)
N3A—C4A—C5A—C6A	−0.9 (3)	N1X—C2X—C3X—C4X	−7.1 (2)
C4A—C5A—C6A—N1A	0.8 (3)	C2X—C3X—C4X—C5X	12.8 (2)
C4A—C5A—C6A—C7A	−179.44 (17)	C2X—N1X—C5X—C4X	10.0 (2)
C2A—N1A—C6A—C5A	−0.2 (3)	C11X—N1X—C5X—C4X	−173.86 (19)
C2A—N1A—C6A—C7A	−179.98 (16)	C3X—C4X—C5X—N1X	−13.7 (2)
C5A—C6A—C7A—O8A	−2.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21X	0.81 (2)	1.92 (2)	2.707 (2)	165 (2)
N3A—H3A···S21Aⁱ	0.88 (2)	2.48 (2)	3.3421 (17)	167.5 (19)

Symmetry code: (i) −x, −y+2, −z+1.

(VI) 2,4-Diaminopyrimidinium 6-methoxymethyl-2-thiouracilate top

Crystal data top

C₄H₇N₄⁺·C₆H₇N₂O₂S⁻	F(000) = 592
M_r = 282.33	D_x = 1.468 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.6843 (4) Å	Cell parameters from 6197 reflections
b = 13.9818 (19) Å	θ = 2.6–27.2°
c = 19.5128 (19) Å	µ = 0.26 mm⁻¹
β = 91.450 (8)°	T = 173 K
V = 1277.6 (2) Å³	Needle, colourless
Z = 4	0.24 × 0.11 × 0.09 mm

Data collection top

Stoe IPDS II two-circle diffractometer	1706 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.166
ω scans	θ_max = 26.9°, θ_min = 2.6°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −5→5
T_min = 0.555, T_max = 1.000	k = −17→17
11870 measured reflections	l = −24→24
2702 independent reflections

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.068	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.168	w = 1/[σ²(F_o²) + (0.0789P)²] where P = (F_o² + 2F_c²)/3
S = 0.96	(Δ/σ)_max < 0.001
2702 reflections	Δρ_max = 0.40 e Å⁻³
191 parameters	Δρ_min = −0.34 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
N1A	0.7479 (6)	0.2435 (2)	0.19795 (15)	0.0354 (6)
C2A	0.7478 (7)	0.3381 (2)	0.19214 (18)	0.0371 (8)
S21A	0.95035 (19)	0.40816 (6)	0.24635 (5)	0.0425 (3)
N3A	0.5832 (5)	0.3810 (2)	0.14207 (15)	0.0358 (6)
H3A	0.584 (8)	0.4415 (14)	0.139 (2)	0.043*
C4A	0.4059 (7)	0.3337 (2)	0.09655 (19)	0.0372 (8)
O41A	0.2538 (5)	0.37915 (18)	0.05477 (14)	0.0459 (6)
C5A	0.4172 (7)	0.2321 (3)	0.10203 (19)	0.0417 (8)
H5A	0.3093	0.1929	0.0712	0.050*
C6A	0.5851 (7)	0.1922 (2)	0.15213 (18)	0.0365 (7)
C7A	0.5961 (8)	0.0851 (3)	0.1635 (2)	0.0453 (9)
H7A1	0.7878	0.0678	0.1821	0.054*
H7A2	0.4549	0.0677	0.1982	0.054*
O8A	0.5396 (5)	0.03116 (16)	0.10343 (13)	0.0399 (6)
C9A	0.7828 (8)	0.0259 (3)	0.0615 (2)	0.0546 (10)
H9A1	0.8334	0.0903	0.0461	0.082*
H9A2	0.7393	−0.0146	0.0216	0.082*
H9A3	0.9435	−0.0016	0.0879	0.082*
N1B	0.6451 (6)	0.7657 (2)	0.15944 (16)	0.0381 (7)
H1B	0.754 (7)	0.805 (2)	0.1823 (19)	0.046*
C2B	0.6919 (7)	0.6694 (2)	0.16259 (18)	0.0359 (7)
N21B	0.8959 (6)	0.6389 (2)	0.20503 (17)	0.0403 (7)
H21B	0.987 (7)	0.676 (3)	0.2345 (17)	0.048*
H22B	0.918 (8)	0.5768 (14)	0.210 (2)	0.048*
N3B	0.5437 (6)	0.6076 (2)	0.12437 (15)	0.0376 (6)
C4B	0.3423 (7)	0.6424 (2)	0.08094 (18)	0.0372 (8)
N41B	0.1917 (6)	0.5813 (2)	0.04333 (17)	0.0456 (8)
H41B	0.211 (8)	0.5189 (15)	0.046 (2)	0.055*
H42B	0.056 (6)	0.601 (3)	0.0153 (17)	0.055*
C5B	0.2906 (7)	0.7427 (3)	0.07484 (19)	0.0412 (8)
H5B	0.1524	0.7668	0.0428	0.049*
C6B	0.4426 (7)	0.8016 (3)	0.11553 (18)	0.0390 (8)
H6B	0.4089	0.8686	0.1137	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0393 (14)	0.0334 (14)	0.0330 (16)	0.0027 (11)	−0.0082 (12)	−0.0010 (12)
C2A	0.0361 (16)	0.0387 (18)	0.0360 (19)	0.0057 (14)	−0.0060 (14)	0.0006 (14)
S21A	0.0489 (5)	0.0335 (4)	0.0439 (5)	0.0002 (4)	−0.0211 (4)	−0.0007 (4)
N3A	0.0367 (14)	0.0327 (14)	0.0374 (15)	0.0022 (12)	−0.0122 (12)	0.0003 (12)
C4A	0.0363 (16)	0.0368 (18)	0.0380 (19)	0.0010 (13)	−0.0088 (14)	−0.0001 (14)
O41A	0.0492 (13)	0.0381 (13)	0.0491 (15)	0.0047 (11)	−0.0246 (12)	−0.0002 (11)
C5A	0.0450 (19)	0.040 (2)	0.0390 (19)	−0.0005 (15)	−0.0158 (16)	−0.0049 (15)
C6A	0.0395 (17)	0.0326 (17)	0.0371 (18)	0.0003 (13)	−0.0024 (14)	−0.0004 (14)
C7A	0.056 (2)	0.0358 (19)	0.044 (2)	−0.0024 (16)	−0.0117 (17)	−0.0017 (16)
O8A	0.0415 (12)	0.0367 (12)	0.0412 (14)	−0.0014 (10)	−0.0029 (10)	−0.0049 (11)
C9A	0.048 (2)	0.054 (2)	0.062 (3)	0.0018 (18)	0.0074 (19)	−0.009 (2)
N1B	0.0410 (15)	0.0333 (15)	0.0394 (17)	−0.0031 (12)	−0.0078 (13)	−0.0015 (12)
C2B	0.0355 (16)	0.0351 (17)	0.0370 (18)	−0.0027 (13)	−0.0043 (14)	0.0006 (14)
N21B	0.0450 (16)	0.0319 (15)	0.0431 (18)	−0.0018 (12)	−0.0180 (13)	−0.0002 (13)
N3B	0.0373 (13)	0.0360 (15)	0.0389 (16)	−0.0026 (11)	−0.0095 (12)	0.0014 (12)
C4B	0.0359 (16)	0.0372 (18)	0.0380 (19)	0.0003 (13)	−0.0085 (14)	0.0012 (15)
N41B	0.0473 (16)	0.0382 (16)	0.0501 (18)	0.0026 (13)	−0.0254 (14)	0.0015 (14)
C5B	0.0402 (18)	0.0377 (18)	0.045 (2)	0.0045 (14)	−0.0095 (16)	0.0040 (16)
C6B	0.0418 (17)	0.0333 (18)	0.042 (2)	0.0006 (14)	−0.0029 (15)	0.0067 (15)

Geometric parameters (Å, º) top

N1A—C2A	1.328 (4)	C9A—H9A3	0.9800
N1A—C6A	1.364 (4)	N1B—C6B	1.358 (5)
C2A—N3A	1.367 (4)	N1B—C2B	1.365 (4)
C2A—S21A	1.711 (4)	N1B—H1B	0.865 (19)
N3A—C4A	1.371 (4)	C2B—N21B	1.320 (4)
N3A—H3A	0.848 (19)	C2B—N3B	1.326 (4)
C4A—O41A	1.243 (4)	N21B—H21B	0.877 (19)
C4A—C5A	1.426 (5)	N21B—H22B	0.878 (19)
C5A—C6A	1.358 (5)	N3B—C4B	1.343 (4)
C5A—H5A	0.9500	C4B—N41B	1.319 (5)
C6A—C7A	1.514 (5)	C4B—C5B	1.428 (5)
C7A—O8A	1.413 (4)	N41B—H41B	0.878 (19)
C7A—H7A1	0.9900	N41B—H42B	0.873 (19)
C7A—H7A2	0.9900	C5B—C6B	1.337 (5)
O8A—C9A	1.421 (4)	C5B—H5B	0.9500
C9A—H9A1	0.9800	C6B—H6B	0.9500
C9A—H9A2	0.9800

C2A—N1A—C6A	117.9 (3)	O8A—C9A—H9A3	109.5
N1A—C2A—N3A	119.8 (3)	H9A1—C9A—H9A3	109.5
N1A—C2A—S21A	121.2 (3)	H9A2—C9A—H9A3	109.5
N3A—C2A—S21A	119.0 (3)	C6B—N1B—C2B	120.1 (3)
C2A—N3A—C4A	125.0 (3)	C6B—N1B—H1B	119 (3)
C2A—N3A—H3A	119 (3)	C2B—N1B—H1B	121 (3)
C4A—N3A—H3A	116 (3)	N21B—C2B—N3B	120.1 (3)
O41A—C4A—N3A	120.4 (3)	N21B—C2B—N1B	117.4 (3)
O41A—C4A—C5A	125.3 (3)	N3B—C2B—N1B	122.4 (3)
N3A—C4A—C5A	114.3 (3)	C2B—N21B—H21B	123 (3)
C6A—C5A—C4A	118.8 (3)	C2B—N21B—H22B	118 (3)
C6A—C5A—H5A	120.6	H21B—N21B—H22B	117 (4)
C4A—C5A—H5A	120.6	C2B—N3B—C4B	117.9 (3)
C5A—C6A—N1A	124.1 (3)	N41B—C4B—N3B	118.3 (3)
C5A—C6A—C7A	121.8 (3)	N41B—C4B—C5B	120.1 (3)
N1A—C6A—C7A	114.0 (3)	N3B—C4B—C5B	121.5 (3)
O8A—C7A—C6A	113.7 (3)	C4B—N41B—H41B	124 (3)
O8A—C7A—H7A1	108.8	C4B—N41B—H42B	121 (3)
C6A—C7A—H7A1	108.8	H41B—N41B—H42B	115 (4)
O8A—C7A—H7A2	108.8	C6B—C5B—C4B	118.0 (3)
C6A—C7A—H7A2	108.8	C6B—C5B—H5B	121.0
H7A1—C7A—H7A2	107.7	C4B—C5B—H5B	121.0
C7A—O8A—C9A	111.6 (3)	C5B—C6B—N1B	120.0 (3)
O8A—C9A—H9A1	109.5	C5B—C6B—H6B	120.0
O8A—C9A—H9A2	109.5	N1B—C6B—H6B	120.0
H9A1—C9A—H9A2	109.5

C6A—N1A—C2A—N3A	1.2 (5)	N1A—C6A—C7A—O8A	−153.8 (3)
C6A—N1A—C2A—S21A	−178.9 (3)	C6A—C7A—O8A—C9A	79.4 (4)
N1A—C2A—N3A—C4A	1.7 (5)	C6B—N1B—C2B—N21B	178.5 (3)
S21A—C2A—N3A—C4A	−178.2 (3)	C6B—N1B—C2B—N3B	−0.6 (5)
C2A—N3A—C4A—O41A	176.6 (3)	N21B—C2B—N3B—C4B	−178.6 (3)
C2A—N3A—C4A—C5A	−3.9 (5)	N1B—C2B—N3B—C4B	0.4 (5)
O41A—C4A—C5A—C6A	−177.3 (4)	C2B—N3B—C4B—N41B	−179.2 (3)
N3A—C4A—C5A—C6A	3.2 (5)	C2B—N3B—C4B—C5B	1.0 (5)
C4A—C5A—C6A—N1A	−0.6 (6)	N41B—C4B—C5B—C6B	178.0 (3)
C4A—C5A—C6A—C7A	176.8 (3)	N3B—C4B—C5B—C6B	−2.2 (6)
C2A—N1A—C6A—C5A	−1.7 (5)	C4B—C5B—C6B—N1B	2.0 (5)
C2A—N1A—C6A—C7A	−179.3 (3)	C2B—N1B—C6B—C5B	−0.7 (5)
C5A—C6A—C7A—O8A	28.6 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···N3B	0.85 (2)	2.35 (2)	3.192 (4)	174 (4)
N1B—H1B···S21Aⁱ	0.87 (2)	2.42 (2)	3.280 (3)	176 (4)
N21B—H21B···N1Aⁱ	0.88 (2)	2.02 (2)	2.889 (4)	170 (4)
N21B—H22B···S21A	0.88 (2)	2.47 (2)	3.333 (3)	169 (4)
N41B—H41B···O41A	0.88 (2)	1.97 (2)	2.850 (4)	178 (4)
N41B—H42B···O41Aⁱⁱ	0.87 (2)	1.99 (2)	2.850 (4)	169 (4)
C6B—H6B···O8Aⁱⁱⁱ	0.95	2.36	3.251 (4)	155

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

(VII) 2,4,6-Triaminopyrimidinium 6-methoxymethyl-2-thiouracilate–6-methoxymethyl-2-thiouracil (1/1) top

Crystal data top

C₄H₈N₅⁺·C₆H₇N₂O₂S⁻·C₆H₈N₂O₂S	D_x = 1.507 Mg m⁻³
M_r = 469.55	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P222₁	Cell parameters from 41700 reflections
a = 6.8086 (4) Å	θ = 3.3–26.3°
b = 8.1414 (5) Å	µ = 0.30 mm⁻¹
c = 18.6651 (14) Å	T = 173 K
V = 1034.64 (12) Å³	Block, colourless
Z = 2	0.15 × 0.13 × 0.11 mm
F(000) = 492

Data collection top

Stoe IPDS II two-circle diffractometer	1975 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.025
ω scans	θ_max = 25.9°, θ_min = 3.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −8→8
T_min = 0.566, T_max = 1.000	k = −9→9
17255 measured reflections	l = −22→22
1999 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.024	w = 1/[σ²(F_o²) + (0.030P)² + 0.3621P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.062	(Δ/σ)_max < 0.001
S = 1.13	Δρ_max = 0.18 e Å⁻³
1999 reflections	Δρ_min = −0.18 e Å⁻³
162 parameters	Absolute structure: Refined as an inversion twin.
6 restraints	Absolute structure parameter: 0.66 (9)

Special details top

Refinement. Refined as a 2-component inversion twin.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.2088 (3)	0.5028 (2)	0.08899 (10)	0.0194 (4)
H1A	0.115 (3)	0.548 (3)	0.0638 (13)	0.023*
C2A	0.3466 (3)	0.6089 (3)	0.11521 (11)	0.0186 (4)
S21A	0.31890 (9)	0.81098 (7)	0.10002 (3)	0.02424 (15)
N3A	0.5000 (3)	0.5441 (2)	0.15099 (10)	0.0224 (4)
H3A	0.590 (7)	0.602 (6)	0.171 (3)	0.027*	0.5
C4A	0.5234 (3)	0.3777 (3)	0.16050 (11)	0.0224 (5)
O41A	0.6737 (2)	0.32473 (19)	0.19069 (9)	0.0275 (4)
C5A	0.3714 (3)	0.2718 (3)	0.13413 (13)	0.0246 (5)
H5A	0.3788	0.1565	0.1417	0.029*
C6A	0.2178 (3)	0.3373 (3)	0.09853 (11)	0.0192 (4)
C7A	0.0527 (3)	0.2359 (3)	0.06922 (12)	0.0220 (5)
H7A1	0.1056	0.1376	0.0446	0.026*
H7A2	−0.0338	0.1988	0.1087	0.026*
O8A	−0.0544 (2)	0.3329 (2)	0.02058 (9)	0.0281 (4)
C9A	−0.2150 (4)	0.2467 (4)	−0.01019 (15)	0.0360 (6)
H9A1	−0.1654	0.1566	−0.0400	0.054*
H9A2	−0.2925	0.3220	−0.0398	0.054*
H9A3	−0.2980	0.2019	0.0280	0.054*
C2B	1.0000	0.6519 (4)	0.2500	0.0181 (6)
N21B	1.0000	0.4893 (3)	0.2500	0.0209 (5)
H22B	0.901 (3)	0.436 (3)	0.2300 (13)	0.025*
N3B	0.8501 (3)	0.7307 (2)	0.21802 (10)	0.0189 (4)
H3B	0.749 (6)	0.677 (6)	0.204 (3)	0.023*	0.5
C4B	0.8477 (3)	0.8980 (3)	0.21894 (11)	0.0198 (5)
N41B	0.6963 (3)	0.9717 (2)	0.18818 (12)	0.0303 (5)
H41B	0.600 (4)	0.918 (4)	0.1688 (15)	0.036*
H42B	0.682 (5)	1.074 (3)	0.1932 (15)	0.036*
C5B	1.0000	0.9848 (4)	0.2500	0.0204 (6)
H5B	1.0000	1.1015	0.2500	0.024*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0169 (9)	0.0207 (9)	0.0206 (9)	0.0016 (7)	−0.0026 (7)	0.0027 (7)
C2A	0.0189 (11)	0.0186 (10)	0.0182 (10)	0.0015 (9)	0.0039 (8)	0.0002 (7)
S21A	0.0249 (3)	0.0155 (2)	0.0323 (3)	0.0005 (3)	−0.0089 (2)	0.0006 (2)
N3A	0.0228 (9)	0.0221 (10)	0.0223 (9)	0.0038 (9)	−0.0028 (7)	−0.0001 (7)
C4A	0.0218 (12)	0.0234 (11)	0.0219 (10)	0.0047 (9)	−0.0038 (9)	−0.0006 (8)
O41A	0.0238 (8)	0.0218 (7)	0.0369 (8)	0.0037 (8)	−0.0123 (7)	−0.0010 (7)
C5A	0.0266 (12)	0.0181 (11)	0.0289 (11)	0.0027 (9)	−0.0067 (9)	0.0011 (9)
C6A	0.0197 (10)	0.0198 (10)	0.0179 (9)	0.0004 (8)	0.0017 (8)	0.0000 (8)
C7A	0.0207 (10)	0.0219 (11)	0.0234 (10)	−0.0018 (9)	−0.0036 (9)	0.0041 (9)
O8A	0.0286 (8)	0.0230 (8)	0.0328 (8)	−0.0046 (8)	−0.0133 (7)	0.0044 (7)
C9A	0.0280 (13)	0.0383 (14)	0.0415 (15)	−0.0089 (11)	−0.0154 (12)	0.0056 (11)
C2B	0.0175 (15)	0.0197 (16)	0.0173 (13)	0.000	0.0050 (12)	0.000
N21B	0.0204 (13)	0.0143 (13)	0.0280 (14)	0.000	−0.0069 (11)	0.000
N3B	0.0161 (9)	0.0159 (9)	0.0248 (9)	−0.0006 (7)	−0.0028 (8)	−0.0001 (7)
C4B	0.0210 (12)	0.0182 (10)	0.0203 (10)	0.0011 (9)	−0.0015 (9)	0.0007 (8)
N41B	0.0286 (11)	0.0172 (9)	0.0451 (12)	0.0044 (9)	−0.0164 (10)	−0.0020 (8)
C5B	0.0237 (16)	0.0126 (14)	0.0247 (15)	0.000	−0.0035 (13)	0.000

Geometric parameters (Å, º) top

N1A—C6A	1.361 (3)	C9A—H9A1	0.9800
N1A—C2A	1.366 (3)	C9A—H9A2	0.9800
N1A—H1A	0.88 (2)	C9A—H9A3	0.9800
C2A—N3A	1.347 (3)	C2B—N21B	1.323 (4)
C2A—S21A	1.680 (2)	C2B—N3Bⁱ	1.345 (2)
N3A—C4A	1.375 (3)	C2B—N3B	1.345 (2)
N3A—H3A	0.86 (3)	N21B—H22B	0.88 (2)
C4A—O41A	1.245 (3)	N3B—C4B	1.362 (3)
C4A—C5A	1.435 (3)	N3B—H3B	0.86 (3)
C5A—C6A	1.349 (3)	C4B—N41B	1.324 (3)
C5A—H5A	0.9500	C4B—C5B	1.382 (3)
C6A—C7A	1.498 (3)	N41B—H41B	0.87 (2)
C7A—O8A	1.407 (3)	N41B—H42B	0.84 (2)
C7A—H7A1	0.9900	C5B—C4Bⁱ	1.382 (3)
C7A—H7A2	0.9900	C5B—H5B	0.9500
O8A—C9A	1.421 (3)

C6A—N1A—C2A	123.27 (18)	C7A—O8A—C9A	112.49 (18)
C6A—N1A—H1A	121.3 (18)	O8A—C9A—H9A1	109.5
C2A—N1A—H1A	115.4 (18)	O8A—C9A—H9A2	109.5
N3A—C2A—N1A	117.53 (19)	H9A1—C9A—H9A2	109.5
N3A—C2A—S21A	123.65 (17)	O8A—C9A—H9A3	109.5
N1A—C2A—S21A	118.81 (16)	H9A1—C9A—H9A3	109.5
C2A—N3A—C4A	122.7 (2)	H9A2—C9A—H9A3	109.5
C2A—N3A—H3A	123 (4)	N21B—C2B—N3Bⁱ	118.50 (14)
C4A—N3A—H3A	114 (4)	N21B—C2B—N3B	118.50 (14)
O41A—C4A—N3A	119.7 (2)	N3Bⁱ—C2B—N3B	123.0 (3)
O41A—C4A—C5A	122.7 (2)	C2B—N21B—H22B	119.3 (18)
N3A—C4A—C5A	117.7 (2)	C2B—N3B—C4B	118.7 (2)
C6A—C5A—C4A	119.4 (2)	C2B—N3B—H3B	120 (4)
C6A—C5A—H5A	120.3	C4B—N3B—H3B	120 (4)
C4A—C5A—H5A	120.3	N41B—C4B—N3B	117.2 (2)
C5A—C6A—N1A	119.4 (2)	N41B—C4B—C5B	122.3 (2)
C5A—C6A—C7A	122.9 (2)	N3B—C4B—C5B	120.5 (2)
N1A—C6A—C7A	117.66 (18)	C4B—N41B—H41B	123 (2)
O8A—C7A—C6A	108.38 (18)	C4B—N41B—H42B	119 (2)
O8A—C7A—H7A1	110.0	H41B—N41B—H42B	117 (3)
C6A—C7A—H7A1	110.0	C4B—C5B—C4Bⁱ	118.5 (3)
O8A—C7A—H7A2	110.0	C4B—C5B—H5B	120.8
C6A—C7A—H7A2	110.0	C4Bⁱ—C5B—H5B	120.8
H7A1—C7A—H7A2	108.4

C6A—N1A—C2A—N3A	1.3 (3)	C2A—N1A—C6A—C7A	177.77 (19)
C6A—N1A—C2A—S21A	−179.87 (17)	C5A—C6A—C7A—O8A	−165.2 (2)
N1A—C2A—N3A—C4A	1.2 (3)	N1A—C6A—C7A—O8A	15.5 (3)
S21A—C2A—N3A—C4A	−177.52 (17)	C6A—C7A—O8A—C9A	−180.0 (2)
C2A—N3A—C4A—O41A	176.1 (2)	N21B—C2B—N3B—C4B	178.90 (15)
C2A—N3A—C4A—C5A	−3.3 (3)	N3Bⁱ—C2B—N3B—C4B	−1.10 (15)
O41A—C4A—C5A—C6A	−176.4 (2)	C2B—N3B—C4B—N41B	−178.75 (18)
N3A—C4A—C5A—C6A	3.1 (3)	C2B—N3B—C4B—C5B	2.2 (3)
C4A—C5A—C6A—N1A	−0.7 (3)	N41B—C4B—C5B—C4Bⁱ	179.9 (3)
C4A—C5A—C6A—C7A	−180.0 (2)	N3B—C4B—C5B—C4Bⁱ	−1.12 (15)
C2A—N1A—C6A—C5A	−1.5 (3)

Symmetry code: (i) −x+2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O8Aⁱⁱ	0.88 (2)	2.18 (2)	3.031 (2)	164 (2)
N21B—H22B···O41A	0.88 (2)	1.94 (2)	2.821 (2)	176 (3)
N3A—H3A···N3B	0.86 (3)	2.24 (3)	3.091 (3)	173 (5)
N3B—H3B···N3A	0.86 (3)	2.24 (3)	3.091 (3)	172 (5)
N41B—H41B···S21A	0.87 (2)	2.46 (2)	3.320 (2)	169 (3)
N41B—H42B···O41Aⁱⁱⁱ	0.84 (2)	2.04 (2)	2.879 (3)	171 (3)

Symmetry codes: (ii) x, −y+1, −z; (iii) x, y+1, z.

Crystallization conditions of (I)–(VII) top

PTU is 6-propyl-2-thiouracil, DAPY is 2,4-diaminopyrimidine, DMAC is N,N-dimethylacetamide, MOMTU is 6-methoxymethyl-2-thiouracil, DMF is N,N-dimethylformamide, DMSO is dimethyl sulfoxide, NMP is 1-methylpyrrolidin-2-one and TAPY is 2,4,6-triaminopyrimidine.

Crystal	Compound (1) (mg, mmol)	Coformer (mg, mmol)	Solvent (µl)	Temperature (K)
(I)	PTU (2.5, 0.015)	DAPY (3.4, 0.031)	DMAC (140)	295
(II)	MOMTU (4.0, 0.023)	-	DMF (70)	277
(III)	MOMTU (4.9, 0.028)	-	DMAC (110)	295
(IV)	MOMTU (5.6, 0.033)	DAPY (1.8, 0.016)	DMSO (65)	323
(V)	MOMTU (4.0, 0.023)	-	NMP (70)	277
(VI)	MOMTU (2.8, 0.016)	DAPY (1.8, 0.016)	DMSO (40)	295
(VII)	MOMTU (5.3, 0.031)	TAPY (2.0, 0.016)	DMF (270)	323

Selected torsion angles (°) for the structures containing PTU derived from the Cambridge Structural Database top

CSD refcode	ω (°)	Φ (°)
BUYWOH	173.8	170.3
HAFLAC	176.1	179.7
UXIXUV01	152.9 (3)	-174.9 (3)
	148.6 (3)	-178.8 (3)
CALFUS	162.10 (17)	-78.4 (2)
	150.28 (17)	176.90 (17)
CALGAZ	178.7 (3)	-178.2 (3)
	–178.2 (3)	178.8 (3)
	176.9 (3)	178.1 (3)
	176.7 (3)	178.0 (3)
	-178.4 (3)	-177.4 (3)
	-178.0 (3)	179.8 (3)

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Text
		Plain Text

6-Propyl-2-thio­uracil versus 6-meth­oxy­methyl-2-thio­uracil: enhancing the hydrogen-bonded synthon motif by replacement of a methyl­ene group with an O atom

Supporting information

6-Propyl-2-thiouracil versus 6-methoxymethyl-2-thiouracil: enhancing the hydrogen-bonded synthon motif by replacement of a methylene group with an O atom