N—H...S and N—H...O hydrogen bonds: `pure' and `mixed' R²₂(8) patterns in the crystal structures of eight 2-thio­uracil derivatives

The preferred hydrogen-bonding patterns in the crystal structures of 5-propyl-2-thio­uracil, C₇H₁₀N₂OS, (I), 5-meth­oxy-2-thio­uracil, C₅H₆N₂O₂S, (II), 5-meth­oxy-2-thio­uracil–N,N-di­methyl­acetamide (1/1), C₅H₆N₂O₂S·C₄H₉NO, (IIa), 5,6-dimethyl-2-thio­uracil, C₆H₈N₂OS, (III), 5,6-dimethyl-2-thio­uracil–1-methyl­pyrrolidin-2-one (1/1), C₆H₈N₂OS·C₅H₉NO, (IIIa), 5,6-dimethyl-2-thio­uracil–N,N-di­methyl­formamide (2/1), 2C₆H₈N₂OS·C₃H₇NO, (IIIb), 5,6-dimethyl-2-thio­uracil–N,N-di­methyl­acetamide (2/1), 2C₆H₈N₂OS·C₄H₉NO, (IIIc), and 5,6-dimethyl-2-thio­uracil–di­methyl ­sulfoxide (2/1), 2C₆H₈N₂OS·C₂H₆OS, (IIId), were analysed. All eight structures contain R²₂(8) patterns. In (II), (IIa), (III) and (IIIa), they are formed by two N—H...S hydrogen bonds, and in (I) by alternating pairs of N—H...S and N—H...O hydrogen bonds. In contrast, the structures of (IIIb), (IIIc) and (IIId) contain `mixed' R²₂(8) patterns with one N—H...S and one N—H...O hydrogen bond, as well as R²₂(8) motifs with two N—H...O hydrogen bonds.

S1. Introduction

Active pharmaceutical ingredients (APIs) are usually delivered as solid drugs containing a crystalline form of the API. Due to their higher stablility and reproducibility, the use of crystalline forms is favoured over amorphous forms (Shan & Zaworotko, 2008). Because of poor solubilities APIs may show a low bioavailability. New crystalline forms of APIs with higher solubility and therefore improved bioavailability can be obtained by synthesizing pharmaceutical co-crystals (Blagden et al., 2007; Schultheiss & Newman, 2009; Vishweshwar et al., 2006). Since non-covalent inter­actions like hydrogen bonds play a dominant role in the molecular recognition process during co-crystal formation, it is helpful to know the preferred hydrogen-bonding pattern of an API.

2-Thio­uracil derivatives are potential candidates for the preparation of pharmaceutical co-crystals. They show anti-thyroid activity, since they inhibit the biosynthesis of the thyroid hormone thyroxine as well as its deiodinative metabolism in peripheral tissues, whereby the relative anti-thyroid activity depends on the residues at atoms C5 and C6 of the pyrimidine ring (Hershman & Van Middlesworth, 1962; Hershman, 1964; Visser et al., 1979). In crystal structures of 2-thio­uracil derivatives, R²₂(8) (Bernstein et al., 1995) is the most abundant hydrogen-bonding pattern (Hützler & Bolte, 2013a); these patterns consist of either two N—H···S or two N—H···O hydrogen bonds [`pure' R<sup>2</sup><sub>2</sub>(8) patterns]. In order to find also `mixed' R²₂(8) patterns consisting of one N—H···S and one N—H···O hydrogen bond, we investigated the three 2-thio­uracil derivatives 5-propyl-2-thio­uracil, 5-meth­oxy-2-thio­uracil and 5,6-di­methyl-2-thio­uracil crystallized alone and as co-crystals with a variety of solvents.

S2. Experimental

S2.1. Synthesis and crystallization

Isothermal solvent evaporation experiments under different conditions with commercially available 2-thio­uracil derivatives and various solvents in which they show an appropriate solubility yielded the title eight new crystal structures, (I)-(IIId) (Table 1). All solvents were used as supplied without further purification. In order to optimize the crystal quality, experiments at different temperatures and with varied crystallization rates were carried out. However, for structures (IIa), (IIIa) and (IIId) only moderate improvement of the crystal quality could be observed.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. All H atoms except those of the disordered solvent molecules were initially located by difference Fourier synthesis. Subsequently, all H atoms bonded to C atoms were refined using a riding model, with methyl C—H = 0.98 Å, secondary C—H = 0.99 Å and aromatic C—H = 0.95 Å, and with U_iso(H) = 1.5U_eq(C) for methyl H atoms or 1.2U_eq(C) for secondary and aromatic H atoms. For all methyl groups, except those of the disordered solvent molecules, free rotation about their local threefold axis was allowed.

In (II), (IIa), (IIIb), (IIIc) and (IIId), isotropic refinement of N-bound H atoms resulted in the isotropic displacement parameters of the H atoms being smaller than the corresponding equivalent displacement parameters of the N atoms. Therefore, the isotropic displacement parameters of the H atoms were coupled to the equivalent displacement parameters of the parent N atoms, with U_iso(H) = 1.2U_eq(N). Additionally, in (II), (IIa), (III), (IIIc) and (IIId) the N—H distances were restrained to 0.88 (2) Å.

In (IIa), the DMAC molecules are disordered over a pseudo-mirror plane along O21(X/Y)···C32(X/Y) lying perpendicular to the plane through all non-H atoms of X/Y [site-occupancy factors for the major occupied orientation of 0.669 (12) for X and 0.756 (11) for Y]. For the solvent molecules, similarity restraints for the 1,2 and 1,3 distances were applied, as well as the similar-ADP restraint (SIMU) and rigid-bond restraint (DELU) (SHELXL97; Sheldrick, 2008).

In (III), an isotropic extinction parameter was refined. In (IIIc), the DMAC molecule shows disorder over two equally occupied positions which do not lie in a common plane. Similarity restraints for the 1,2 and 1,3 distances were applied. The methyl groups at C5 of both 5,6-di­methyl-2-thio­uracil molecules show a rotational disorder [site-occupancy factors for the major occupied orientation of 0.70 (2) for C51A and 0.57 (2) for C51B]. In (IIa) and (IIId), respectively, three reflections with bad F_o/F_c agreement were omitted.

S3. Results and discussion

5-Propyl-2-thio­uracil, (I), crystallizes in the triclinic space group P1 with two molecules, A and B, in the asymmetric unit (Fig. 1). The pyrimidine rings of both molecules are planar [r.m.s. deviations for all non-H atoms of the rings = 0.029 Å (for A) and 0.022 Å (for B)] and are tilted towards each other, enclosing a dihedral angle of 30.59 (4)°. The propyl groups exhibit different conformations in A and B: whereas the side chain of molecule A is twisted, with the planes through the ring and the propyl group enclosing a dihedral angle of 73.18 (8)°, it is extended in molecule B, with a dihedral angle of 2.0 (3)°. The molecules are connected by alternating R²₂(8) inter­actions consisting of either two N—H···S or two N—H···O hydrogen bonds, resulting in chains running along the c axis (Fig. 2, Table 3). In the crystal packing, adjacent chains show a tubular arrangement (see extra figure in supplementary information).

5-Meth­oxy-2-thio­uracil, (II), crystallizes in the monoclinic space group P2₁/c with one planar molecule in the asymmetric unit [r.m.s. deviation for all non-H atoms = 0.012 Å], whereby atoms C4A and C52A exhibit an anti-periplanar conformation (Fig. 3). In the crystal packing, the molecules are connected to homodimers stabilized by R²₂(8) N—H···S hydrogen bonds. Adjacent homodimers are linked to each other by bifurcated R²₁(5) N—H···O hydrogen bonds and enclose a dihedral angle of 6.75 (7)°, resulting in layers parallel to (102) (Fig. 4, Table 4).

The DMAC solvate, (IIa), crystallizes in the monoclinic space group P2₁/m. The asymmetric unit consists of two molecules of 5-meth­oxy-2-thio­uracil, A and B, and two disordered DMAC molecules, whereby all four molecules lie on a mirror plane. Molecules A and B are connected by R²₂(8) N—H···S hydrogen bonds and show further N—H···O hydrogen bonds with the solvent molecules (Fig. 5, Table 5). In the crystal packing, the A–B homodimers are arranged parallel to (010) (Fig. 6).

5,6-Di­methyl-2-thio­uracil, (III), crystallizes in the monoclinic space group P2₁/c with one planar molecule in the asymmetric unit [r.m.s. deviation for all non-H atoms = 0.037 Å] (Fig. 7). The molecules show R²₂(8) N—H···S hydrogen-bonding inter­actions stabilizing the homodimers, which are further connected by N—H···O hydrogen bonds, yielding R⁴₄(16) patterns and thus forming ribbons running along the a axis (Fig. 8, Table 6).

The NMP solvate, (IIIa), crystallizes in the orthorhombic space group Pbca with one planar 5,6-di­methyl-2-thio­uracil molecule, A, [r.m.s. deviation for all non-H atoms = 0.015 Å] and one NMP molecule, X, in the asymmetric unit, which are connected by an N—H···O hydrogen bond (Fig. 9). The planes through all non-H atoms of A and X, respectively, enclose a dihedral angle of 55.49 (6)°. In the crystal packing, the 5,6-di­methyl-2-thio­uracil molecules form dimers parallel to (010) stabilized by R²₂(8) N—H···S hydrogen bonds (Fig. 10, Table 7).

The DMF solvate, (IIIb), crystallizes in the triclinic space group P1 with two 5,6-di­methyl-2-thio­uracil molecules, A and B, and one solvent molecule, X, in the asymmetric unit; all three molecules lie in a common plane [r.m.s. deviation for all non-H atoms = 0.048 Å]. This time molecules A and B are linked by one N—H···S and one N—H···O hydrogen bond, thus forming a `mixed' R²₂(8) pattern, and molecule B is further connected to the solvent molecule by an N—H···O hydrogen bond (Fig. 11). In the crystal packing, the 5,6-di­methyl-2-thio­uracil molecules form tetra­mers through two additional R²₂(8) N—H···O hydrogen bonds. The tetra­mers are arranged parallel to (213) and show only van der Waals inter­actions between each other (Fig. 12, Table 8).

The asymmetric unit of the DMAC solvate, (IIIc), which also crystallizes in the space group P1, consists of two 5,6-di­methyl-2-thio­uracil molecules, A and B, and one DMAC molecule. This last is disordered over two positions, X and Y, whereby only X lies in a common plane with A and B (Fig. 13a; r.m.s. deviation for all non-H atoms of A, B and X = 0.096 Å). The planes through X and Y enclose a dihedral angle of 70.71 (16)° (Fig. 13b). As in (IIIb), molecules A and B are connected by a `mixed' R²₂(8) pattern consisting of one N—H···S and one N—H···O hydrogen bond, and molecule B forms one additional N—H···O hydrogen bond with the solvent molecule. Stabilized by two further R²₂(8) N—H···O hydrogen bonds, the 5,6-di­methyl-2-thio­uracil molecules are connected into tetra­mers that are arranged parallel to (210) (Fig. 14, Table 9).

Compound (IIId) crystallizes in the monoclinic space group P2₁/n with two coplanar 5,6-di­methyl-2-thio­uracil molecules, A and B (r.m.s. deviation for all non-H atoms = 0.062 Å), and one DMSO molecule, X, in the asymmetric unit (Fig. 15). The planes through molecules A and B and through all non-H atoms of X, respectively, are almost perpendicular [dihedral angle = 78.93 (17)°]. Molecules A and B are again connected to each other via a `mixed' R²₂(8) pattern, and molecule B is further connected to X by an N—H···O hydrogen bond. Similar to (IIIc), in the crystal structure one additional R²₂(8) N—H···O hydrogen-bonding inter­action is formed between molecules A, yielding tetra­mers that are arranged alternately parallel to (221) and (221), respectively (Fig. 16, Table 10).

All eight structures contain R²₂(8) homodimers, which is in agreement with the result of a previous Cambridge Structural Database (CSD; Allen, 2002) substructure search for 2-thio­uracil derivatives (Hützler & Bolte, 2013a). In (I), (II), (IIa), (III) and (IIIa), the R²₂(8) motifs consist of two N—H···S hydrogen bonds, and (I) shows additional R²₂(8) motifs consisting of two N—H···O hydrogen bonds. In (IIIb), (IIIc) and (IIId), `mixed' R²₂(8) patterns containing one N—H···S and one N—H···O hydrogen bond are formed, as well as R²₂(8) motifs with two N—H···O hydrogen bonds. These three structures show the same hydrogen-bonding pattern between the 5,6-di­methyl-2-thio­uracil molecules and the respective solvent molecules, while the crystal packing of the tetra­mers is clearly different.

In structures (IIa) and (IIIa), the O atoms of the 2-thio­uracil group do not form hydrogen bonds but participate only in van der Waals inter­actions. Comparing (I) with the structure of the isomeric compound 6-propyl-2-thio­uracil (CSD refcode UXIXUV01; Tutughamiarso & Egert, 2011), equal hydrogen-bonding patterns are found in both structures but differences are observed for the conformation of the propyl side-chains. Whereas the dihedral angle between the planes through the propyl group and the pyrimidine ring is similar for both molecules in UXIXUV01 [26.0 (2) and 29.8 (2)°, respectively], it is clearly different in (I) [73.18 (8) and 2.0 (3)°]. A search of the CSD (Version 5.34 of November 2012, plus three updates; Allen, 2002) yielded one further structure of each of the two isomers, namely the structure of the dioxane monosolvate of 5-propyl-2-thio­uracil (Hützler & Bolte, 2013b) and the dioxane hemisolvate of 6-propyl-2-thio­uracil (refcode BUWYOH; Okabe et al., 1983). In both structures, R²₂(8) N—H···O homodimers are formed and the propyl side-chains are coplanar with the pyrimidine rings, whereas the S atoms do not participate in hydrogen bonds.

In summary, and in agreement with our previous work on 2-thio­uracil derivatives, R²₂(8) is the favoured hydrogen-bonding pattern in all eight structures (I)–(IIId). In five of the structures, R²₂(8) N—H···S hydrogen bonds are formed, and three structures contain `mixed' R²₂(8) patterns with one N—H···S and one N—H···O hydrogen bond. Additional R²₂(8) N—H···O hydrogen bonds are observed in four of these structures.

Related literature

For related literature, see: Allen (2002); Bernstein et al. (1995); Blagden et al. (2007); Hützler & Bolte (2013a, 2013b); Hershman (1964); Hershman & Van Middlesworth (1962); Okabe et al. (1983); Schultheiss & Newman (2009); Shan & Zaworotko (2008); Sheldrick (2008); Tutughamiarso & Egert (2011); Vishweshwar et al. (2006); Visser et al. (1979).

Computing details

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: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

Fig. 1. A perspective view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate N—H···S hydrogen bonds.

Fig. 2. A partial packing diagram for (I). N—H···S and N—H···O hydrogen bonds are shown as dashed lines. [Symmetry code: (i) x, y, z - 1.]

Fig. 3. A perspective view of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Fig. 4. A partial packing diagram for (II), showing a layer parallel to (102). Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) x + 1, -y + 3/2, z + 1/2; (ii) -x + 1, -y + 1, -z + 1.]

Fig. 5. A perspective view of (IIa), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds. The dimethylacetamide molecules X and Y are disordered and only the major occupied sites are shown.

Fig. 6. A partial packing diagram for (IIa), showing the dimers arranged parallel to (010). Hydrogen bonds are shown as dashed lines.

Fig. 7. A perspective view of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Fig. 8. A partial packing diagram for (III). Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) -x + 1, -y + 1, -z + 1; (ii) x - 1, y, z.]

Fig. 9. A perspective view of (IIIa), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates an N—H···O hydrogen bond.

Fig. 10. A partial packing diagram for (IIIa). Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) -x + 2, -y + 1, -z + 1.]

Fig. 11. A perspective view of (IIIb), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.

Fig. 12. A partial packing diagram for (IIIb). Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) -x, -y - 1, -z + 1.]

Fig. 13. A perspective view of (IIIc), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. In (a) only site X, and in (b) only site Y, of the disordered DMAC molecule is shown (site occupancy factors of 0.50). Dashed lines indicate hydrogen bonds.

Fig. 14. A partial packing diagram for (IIIc). Hydrogen bonds are shown as dashed lines. The disordered DMAC molecules are not displayed. [Symmetry code: (i) -x + 1, -y + 2, -z + 1.]

Fig. 15. A perspective view of (IIId), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.

Fig. 16. A partial packing diagram for (IIId). Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) -x + 2, - y + 1, -z.]

(I) 5-Propyl-2-thiouracil

Crystal data

C7H10N2OS	Z = 4
Mr = 170.23	F(000) = 360
Triclinic, P1	Dx = 1.332 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6637 (10) Å	Cell parameters from 796 reflections
b = 10.3098 (13) Å	θ = 4.8–25.8°
c = 10.7255 (13) Å	µ = 0.33 mm^−1
α = 76.253 (10)°	T = 173 K
β = 71.401 (9)°	Plate, colourless
γ = 70.983 (9)°	0.30 × 0.22 × 0.10 mm
V = 848.81 (18) Å^3

Data collection

Stoe IPDS II two-circle diffractometer	3163 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	2609 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.062
ω scans	θmax = 25.6°, θmin = 3.7°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→10
Tmin = 0.909, Tmax = 0.968	k = −10→12
6626 measured reflections	l = −13→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0665P)^2] where P = (Fo^2 + 2Fc^2)/3
3163 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.28 e Å^−3
0 restraints	Δρmin = −0.27 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.3051 (2)	0.45551 (17)	0.82058 (16)	0.0235 (3)
H1A	0.319 (3)	0.437 (3)	0.742 (3)	0.037 (7)*
C2A	0.2239 (2)	0.3828 (2)	0.92877 (18)	0.0212 (4)
S21A	0.16424 (7)	0.24586 (5)	0.92301 (5)	0.02809 (16)
N3A	0.19600 (19)	0.42747 (17)	1.04530 (15)	0.0207 (3)
H3A	0.140 (3)	0.388 (3)	1.116 (3)	0.039 (7)*
C4A	0.2502 (2)	0.53309 (19)	1.06252 (18)	0.0200 (4)
O41A	0.22742 (17)	0.55611 (15)	1.17572 (13)	0.0256 (3)
C5A	0.3350 (2)	0.60788 (19)	0.94146 (18)	0.0205 (4)
C6A	0.3576 (2)	0.5649 (2)	0.82643 (19)	0.0228 (4)
H6A	0.4124	0.6125	0.7458	0.027*
C7A	0.3900 (2)	0.7288 (2)	0.94915 (19)	0.0247 (4)
H7A1	0.4838	0.7422	0.8698	0.030*
H7A2	0.4337	0.7074	1.0286	0.030*
C8A	0.2484 (3)	0.8625 (2)	0.9569 (2)	0.0315 (5)
H8A1	0.1536	0.8483	1.0351	0.038*
H8A2	0.2898	0.9356	0.9705	0.038*
C9A	0.1833 (3)	0.9120 (2)	0.8338 (3)	0.0382 (5)
H9A1	0.2763	0.9268	0.7559	0.057*
H9A2	0.0940	0.9994	0.8440	0.057*
H9A3	0.1374	0.8420	0.8218	0.057*
N1B	0.1119 (2)	0.28846 (18)	0.62556 (16)	0.0237 (4)
H1B	0.142 (3)	0.278 (3)	0.698 (3)	0.035 (7)*
C2B	0.1926 (2)	0.3567 (2)	0.51504 (18)	0.0209 (4)
S21B	0.34459 (6)	0.42710 (5)	0.51087 (5)	0.02622 (15)
N3B	0.1442 (2)	0.36483 (18)	0.40380 (15)	0.0223 (3)
H3B	0.185 (3)	0.416 (3)	0.330 (3)	0.035 (6)*
C4B	0.0271 (2)	0.3032 (2)	0.39524 (19)	0.0233 (4)
O41B	0.00085 (18)	0.31258 (16)	0.28713 (13)	0.0301 (3)
C5B	−0.0556 (2)	0.2313 (2)	0.51874 (19)	0.0225 (4)
C6B	−0.0116 (2)	0.2296 (2)	0.62874 (19)	0.0247 (4)
H6B	−0.0676	0.1864	0.7116	0.030*
C7B	−0.1881 (2)	0.1669 (2)	0.5174 (2)	0.0284 (4)
H7B1	−0.1354	0.0985	0.4546	0.034*
H7B2	−0.2777	0.2404	0.4829	0.034*
C8B	−0.2703 (3)	0.0952 (3)	0.6508 (2)	0.0406 (6)
H8B1	−0.3284	0.1636	0.7134	0.049*
H8B2	−0.1818	0.0227	0.6874	0.049*
C9B	−0.3979 (3)	0.0289 (3)	0.6388 (3)	0.0535 (7)
H9B1	−0.4866	0.1007	0.6038	0.080*
H9B2	−0.4489	−0.0163	0.7267	0.080*
H9B3	−0.3402	−0.0402	0.5783	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0308 (9)	0.0260 (9)	0.0152 (8)	−0.0110 (7)	−0.0049 (6)	−0.0030 (6)
C2A	0.0207 (8)	0.0228 (9)	0.0196 (9)	−0.0042 (7)	−0.0075 (7)	−0.0019 (7)
S21A	0.0417 (3)	0.0269 (3)	0.0228 (3)	−0.0177 (2)	−0.0114 (2)	−0.00111 (19)
N3A	0.0240 (8)	0.0231 (8)	0.0161 (8)	−0.0095 (7)	−0.0051 (6)	−0.0007 (6)
C4A	0.0203 (8)	0.0196 (9)	0.0194 (9)	−0.0045 (7)	−0.0067 (7)	−0.0009 (7)
O41A	0.0341 (7)	0.0284 (7)	0.0172 (7)	−0.0116 (6)	−0.0068 (5)	−0.0044 (5)
C5A	0.0197 (8)	0.0197 (9)	0.0205 (9)	−0.0049 (7)	−0.0059 (7)	0.0000 (7)
C6A	0.0245 (9)	0.0233 (10)	0.0198 (9)	−0.0084 (8)	−0.0057 (7)	0.0008 (7)
C7A	0.0277 (9)	0.0248 (10)	0.0241 (10)	−0.0115 (8)	−0.0085 (8)	0.0002 (8)
C8A	0.0362 (11)	0.0255 (11)	0.0350 (11)	−0.0095 (9)	−0.0103 (9)	−0.0055 (9)
C9A	0.0399 (12)	0.0281 (11)	0.0471 (14)	−0.0098 (9)	−0.0193 (10)	0.0051 (10)
N1B	0.0279 (8)	0.0298 (9)	0.0171 (8)	−0.0124 (7)	−0.0079 (6)	−0.0014 (7)
C2B	0.0218 (8)	0.0220 (9)	0.0187 (9)	−0.0049 (7)	−0.0047 (7)	−0.0051 (7)
S21B	0.0286 (3)	0.0364 (3)	0.0193 (2)	−0.0175 (2)	−0.00474 (18)	−0.00463 (19)
N3B	0.0256 (8)	0.0282 (9)	0.0154 (8)	−0.0123 (7)	−0.0048 (6)	−0.0017 (7)
C4B	0.0258 (9)	0.0262 (10)	0.0197 (9)	−0.0093 (8)	−0.0059 (7)	−0.0034 (7)
O41B	0.0345 (7)	0.0442 (9)	0.0185 (7)	−0.0213 (7)	−0.0079 (6)	−0.0012 (6)
C5B	0.0223 (9)	0.0236 (9)	0.0222 (9)	−0.0070 (8)	−0.0063 (7)	−0.0027 (7)
C6B	0.0274 (9)	0.0260 (10)	0.0217 (9)	−0.0107 (8)	−0.0064 (7)	−0.0006 (8)
C7B	0.0278 (10)	0.0310 (11)	0.0302 (11)	−0.0137 (9)	−0.0084 (8)	−0.0026 (9)
C8B	0.0373 (12)	0.05 (14)	0.0379 (12)	−0.0257 (11)	−0.0074 (10)	0.0032 (11)
C9B	0.0435 (14)	0.0550 (16)	0.0675 (18)	−0.0324 (13)	−0.0129 (13)	0.0050 (14)

Geometric parameters (Å, º)

N1A—C2A	1.347 (2)	N1B—C2B	1.336 (2)
N1A—C6A	1.367 (2)	N1B—C6B	1.380 (2)
N1A—H1A	0.87 (3)	N1B—H1B	0.87 (3)
C2A—N3A	1.357 (2)	C2B—N3B	1.362 (2)
C2A—S21A	1.6738 (19)	C2B—S21B	1.6827 (18)
N3A—C4A	1.387 (2)	N3B—C4B	1.396 (2)
N3A—H3A	0.85 (3)	N3B—H3B	0.88 (3)
C4A—O41A	1.234 (2)	C4B—O41B	1.227 (2)
C4A—C5A	1.451 (2)	C4B—C5B	1.446 (3)
C5A—C6A	1.344 (3)	C5B—C6B	1.346 (3)
C5A—C7A	1.500 (2)	C5B—C7B	1.507 (2)
C6A—H6A	0.9500	C6B—H6B	0.9500
C7A—C8A	1.516 (3)	C7B—C8B	1.513 (3)
C7A—H7A1	0.9900	C7B—H7B1	0.9900
C7A—H7A2	0.9900	C7B—H7B2	0.9900
C8A—C9A	1.513 (3)	C8B—C9B	1.527 (3)
C8A—H8A1	0.9900	C8B—H8B1	0.9900
C8A—H8A2	0.9900	C8B—H8B2	0.9900
C9A—H9A1	0.9800	C9B—H9B1	0.9800
C9A—H9A2	0.9800	C9B—H9B2	0.9800
C9A—H9A3	0.9800	C9B—H9B3	0.9800
C2A—N1A—C6A	123.21 (17)	C2B—N1B—C6B	123.23 (17)
C2A—N1A—H1A	119.4 (17)	C2B—N1B—H1B	118.0 (17)
C6A—N1A—H1A	117.2 (17)	C6B—N1B—H1B	118.7 (17)
N1A—C2A—N3A	114.69 (16)	N1B—C2B—N3B	115.11 (16)
N1A—C2A—S21A	123.52 (14)	N1B—C2B—S21B	123.23 (14)
N3A—C2A—S21A	121.78 (14)	N3B—C2B—S21B	121.66 (14)
C2A—N3A—C4A	126.52 (16)	C2B—N3B—C4B	126.00 (16)
C2A—N3A—H3A	118.1 (18)	C2B—N3B—H3B	118.9 (16)
C4A—N3A—H3A	115.4 (18)	C4B—N3B—H3B	115.0 (16)
O41A—C4A—N3A	119.80 (16)	O41B—C4B—N3B	119.57 (17)
O41A—C4A—C5A	124.56 (16)	O41B—C4B—C5B	124.65 (17)
N3A—C4A—C5A	115.62 (16)	N3B—C4B—C5B	115.79 (16)
C6A—C5A—C4A	117.07 (16)	C6B—C5B—C4B	117.29 (16)
C6A—C5A—C7A	123.31 (16)	C6B—C5B—C7B	124.17 (17)
C4A—C5A—C7A	119.61 (16)	C4B—C5B—C7B	118.51 (17)
C5A—C6A—N1A	122.76 (17)	C5B—C6B—N1B	122.43 (17)
C5A—C6A—H6A	118.6	C5B—C6B—H6B	118.8
N1A—C6A—H6A	118.6	N1B—C6B—H6B	118.8
C5A—C7A—C8A	113.00 (16)	C5B—C7B—C8B	115.32 (17)
C5A—C7A—H7A1	109.0	C5B—C7B—H7B1	108.4
C8A—C7A—H7A1	109.0	C8B—C7B—H7B1	108.4
C5A—C7A—H7A2	109.0	C5B—C7B—H7B2	108.4
C8A—C7A—H7A2	109.0	C8B—C7B—H7B2	108.4
H7A1—C7A—H7A2	107.8	H7B1—C7B—H7B2	107.5
C9A—C8A—C7A	113.33 (18)	C7B—C8B—C9B	111.6 (2)
C9A—C8A—H8A1	108.9	C7B—C8B—H8B1	109.3
C7A—C8A—H8A1	108.9	C9B—C8B—H8B1	109.3
C9A—C8A—H8A2	108.9	C7B—C8B—H8B2	109.3
C7A—C8A—H8A2	108.9	C9B—C8B—H8B2	109.3
H8A1—C8A—H8A2	107.7	H8B1—C8B—H8B2	108.0
C8A—C9A—H9A1	109.5	C8B—C9B—H9B1	109.5
C8A—C9A—H9A2	109.5	C8B—C9B—H9B2	109.5
H9A1—C9A—H9A2	109.5	H9B1—C9B—H9B2	109.5
C8A—C9A—H9A3	109.5	C8B—C9B—H9B3	109.5
H9A1—C9A—H9A3	109.5	H9B1—C9B—H9B3	109.5
H9A2—C9A—H9A3	109.5	H9B2—C9B—H9B3	109.5
C6A—N1A—C2A—N3A	0.7 (3)	C6B—N1B—C2B—N3B	0.1 (3)
C6A—N1A—C2A—S21A	−178.14 (15)	C6B—N1B—C2B—S21B	−179.39 (16)
N1A—C2A—N3A—C4A	−3.6 (3)	N1B—C2B—N3B—C4B	−3.5 (3)
S21A—C2A—N3A—C4A	175.22 (14)	S21B—C2B—N3B—C4B	176.00 (15)
C2A—N3A—C4A—O41A	−174.34 (18)	C2B—N3B—C4B—O41B	−176.28 (19)
C2A—N3A—C4A—C5A	4.4 (3)	C2B—N3B—C4B—C5B	3.7 (3)
O41A—C4A—C5A—C6A	176.48 (18)	O41B—C4B—C5B—C6B	179.5 (2)
N3A—C4A—C5A—C6A	−2.2 (2)	N3B—C4B—C5B—C6B	−0.5 (3)
O41A—C4A—C5A—C7A	−4.6 (3)	O41B—C4B—C5B—C7B	−2.2 (3)
N3A—C4A—C5A—C7A	176.74 (16)	N3B—C4B—C5B—C7B	177.79 (17)
C4A—C5A—C6A—N1A	−0.3 (3)	C4B—C5B—C6B—N1B	−2.6 (3)
C7A—C5A—C6A—N1A	−179.20 (17)	C7B—C5B—C6B—N1B	179.24 (19)
C2A—N1A—C6A—C5A	1.2 (3)	C2B—N1B—C6B—C5B	2.9 (3)
C6A—C5A—C7A—C8A	96.4 (2)	C6B—C5B—C7B—C8B	−1.1 (3)
C4A—C5A—C7A—C8A	−82.4 (2)	C4B—C5B—C7B—C8B	−179.3 (2)
C5A—C7A—C8A—C9A	−64.1 (2)	C5B—C7B—C8B—C9B	−178.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···S21B	0.87 (3)	2.44 (3)	3.3030 (18)	170 (2)
N3A—H3A···O41B^i	0.85 (3)	1.99 (3)	2.835 (2)	175 (3)
N1B—H1B···S21A	0.87 (3)	2.42 (3)	3.2715 (18)	168 (2)
N3B—H3B···O41A^ii	0.88 (3)	1.94 (3)	2.811 (2)	168 (2)

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

(II) 5-Methoxy-2-thiouracil

Crystal data

C5H6N2O2S	F(000) = 328
Mr = 158.18	Dx = 1.604 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5816 reflections
a = 4.3141 (6) Å	θ = 4.3–26.0°
b = 16.9101 (18) Å	µ = 0.43 mm^−1
c = 8.9965 (12) Å	T = 173 K
β = 93.593 (10)°	Plate, colourless
V = 655.02 (14) Å^3	0.32 × 0.11 × 0.06 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	1228 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	1072 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.077
ω scans	θmax = 25.6°, θmin = 4.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −5→5
Tmin = 0.876, Tmax = 0.975	k = −19→20
5186 measured reflections	l = −10→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.061P)^2 + 0.3198P] where P = (Fo^2 + 2Fc^2)/3
1228 reflections	(Δ/σ)max = 0.026
98 parameters	Δρmax = 0.39 e Å^−3
2 restraints	Δρmin = −0.22 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.7438 (4)	0.69293 (11)	0.6715 (2)	0.0234 (4)
H1A	0.873 (6)	0.6937 (17)	0.749 (3)	0.028*
C2A	0.6591 (5)	0.62132 (13)	0.6188 (3)	0.0232 (5)
S21A	0.81851 (13)	0.53700 (3)	0.68480 (7)	0.0281 (2)
N3A	0.4334 (4)	0.62184 (11)	0.5068 (2)	0.0232 (4)
H3A	0.379 (6)	0.5762 (12)	0.470 (3)	0.028*
C4A	0.2857 (5)	0.68713 (13)	0.4440 (3)	0.0229 (5)
O41A	0.0816 (4)	0.68022 (10)	0.34415 (19)	0.0290 (4)
C5A	0.3928 (5)	0.76207 (14)	0.5064 (3)	0.0233 (5)
O51A	0.2461 (4)	0.82563 (9)	0.44278 (19)	0.0272 (4)
C52A	0.3363 (7)	0.90080 (15)	0.5061 (3)	0.0344 (6)
H52A	0.2944	0.9015	0.6119	0.052*
H52B	0.2174	0.9430	0.4540	0.052*
H52C	0.5585	0.9093	0.4956	0.052*
C6A	0.6145 (5)	0.76281 (14)	0.6169 (3)	0.0240 (5)
H6A	0.6842	0.8118	0.6584	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0205 (10)	0.0279 (10)	0.0210 (10)	−0.0007 (7)	−0.0042 (8)	−0.0001 (7)
C2A	0.0191 (11)	0.0287 (12)	0.0220 (12)	−0.0027 (8)	0.0026 (9)	0.0019 (9)
S21A	0.0287 (3)	0.0263 (3)	0.0280 (4)	0.0008 (2)	−0.0079 (2)	0.0015 (2)
N3A	0.0229 (10)	0.0238 (10)	0.0223 (10)	−0.0029 (7)	−0.0040 (7)	−0.0003 (7)
C4A	0.0204 (11)	0.0271 (11)	0.0211 (12)	−0.0002 (8)	0.0017 (9)	0.0005 (9)
O41A	0.0288 (9)	0.0305 (9)	0.0260 (9)	0.0001 (7)	−0.0112 (7)	−0.0007 (7)
C5A	0.0211 (11)	0.0270 (12)	0.0219 (11)	−0.0005 (8)	0.0015 (9)	0.0008 (9)
O51A	0.0287 (9)	0.0234 (8)	0.0283 (9)	0.0014 (6)	−0.0085 (7)	−0.0004 (7)
C52A	0.0417 (15)	0.0242 (12)	0.0360 (15)	−0.0001 (10)	−0.0071 (12)	−0.0019 (10)
C6A	0.0221 (11)	0.0259 (11)	0.0239 (11)	−0.0016 (8)	0.0002 (9)	−0.0015 (9)

Geometric parameters (Å, º)

N1A—C2A	1.343 (3)	C4A—C5A	1.450 (3)
N1A—C6A	1.384 (3)	C5A—C6A	1.336 (3)
N1A—H1A	0.862 (18)	C5A—O51A	1.356 (3)
C2A—N3A	1.357 (3)	O51A—C52A	1.437 (3)
C2A—S21A	1.675 (2)	C52A—H52A	0.9800
N3A—C4A	1.378 (3)	C52A—H52B	0.9800
N3A—H3A	0.867 (17)	C52A—H52C	0.9800
C4A—O41A	1.223 (3)	C6A—H6A	0.9500
C2A—N1A—C6A	123.4 (2)	C6A—C5A—C4A	119.5 (2)
C2A—N1A—H1A	116.5 (19)	O51A—C5A—C4A	113.59 (19)
C6A—N1A—H1A	119.9 (19)	C5A—O51A—C52A	115.23 (18)
N1A—C2A—N3A	115.0 (2)	O51A—C52A—H52A	109.5
N1A—C2A—S21A	123.09 (18)	O51A—C52A—H52B	109.5
N3A—C2A—S21A	121.87 (17)	H52A—C52A—H52B	109.5
C2A—N3A—C4A	127.0 (2)	O51A—C52A—H52C	109.5
C2A—N3A—H3A	116.4 (19)	H52A—C52A—H52C	109.5
C4A—N3A—H3A	117 (2)	H52B—C52A—H52C	109.5
O41A—C4A—N3A	121.2 (2)	C5A—C6A—N1A	120.7 (2)
O41A—C4A—C5A	124.4 (2)	C5A—C6A—H6A	119.7
N3A—C4A—C5A	114.4 (2)	N1A—C6A—H6A	119.7
C6A—C5A—O51A	126.9 (2)
C6A—N1A—C2A—N3A	−0.2 (3)	O41A—C4A—C5A—O51A	−0.4 (3)
C6A—N1A—C2A—S21A	179.57 (17)	N3A—C4A—C5A—O51A	179.68 (19)
N1A—C2A—N3A—C4A	−0.3 (3)	C6A—C5A—O51A—C52A	−2.1 (3)
S21A—C2A—N3A—C4A	179.89 (18)	C4A—C5A—O51A—C52A	177.4 (2)
C2A—N3A—C4A—O41A	−179.1 (2)	O51A—C5A—C6A—N1A	179.8 (2)
C2A—N3A—C4A—C5A	0.8 (3)	C4A—C5A—C6A—N1A	0.4 (3)
O41A—C4A—C5A—C6A	179.1 (2)	C2A—N1A—C6A—C5A	0.2 (3)
N3A—C4A—C5A—C6A	−0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O51A^i	0.86 (2)	2.32 (2)	3.176 (3)	170 (3)
N1A—H1A···O41A^i	0.86 (2)	2.45 (3)	2.975 (3)	120 (2)
N3A—H3A···S21A^ii	0.87 (2)	2.49 (2)	3.337 (2)	167 (3)

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

(IIa) 5-Methoxy-2-thiouracil–dimethylacetamide (1/1)

Crystal data

C5H6N2O2S·C4H9NO	F(000) = 520
Mr = 245.30	Dx = 1.383 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 6964 reflections
a = 13.225 (3) Å	θ = 3.3–26.3°
b = 6.4726 (8) Å	µ = 0.27 mm^−1
c = 13.867 (3) Å	T = 173 K
β = 97.170 (15)°	Needle, colourless
V = 1177.7 (4) Å^3	0.30 × 0.18 × 0.12 mm
Z = 4

Data collection

Stoe IPDS II two-circle- diffractometer	2470 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	1767 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.116
ω scans	θmax = 26.0°, θmin = 3.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −16→16
Tmin = 0.923, Tmax = 0.968	k = −6→7
9319 measured reflections	l = −16→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.077	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0805P)^2 + 1.0888P] where P = (Fo^2 + 2Fc^2)/3
2470 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.50 e Å^−3
260 restraints	Δρmin = −0.42 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.4575 (3)	0.2500	0.4657 (3)	0.0276 (12)
H1A	0.521 (2)	0.2500	0.457 (4)	0.033*
C2A	0.3837 (4)	0.2500	0.3902 (4)	0.0243 (12)
S21A	0.40863 (10)	0.2500	0.27431 (9)	0.0307 (4)
N3A	0.2870 (3)	0.2500	0.4151 (3)	0.0231 (10)
H3A	0.238 (3)	0.2500	0.367 (3)	0.028*
C4A	0.2582 (4)	0.2500	0.5079 (4)	0.0247 (12)
O41A	0.1683 (3)	0.2500	0.5203 (3)	0.0336 (11)
C5A	0.3443 (4)	0.2500	0.5847 (3)	0.0250 (12)
O51A	0.3163 (3)	0.2500	0.6754 (3)	0.0322 (10)
C52A	0.3996 (5)	0.2500	0.7525 (4)	0.0351 (15)
H5AA	0.3728	0.2500	0.8153	0.053*
H5AB	0.4413	0.3736	0.7475	0.053*	0.50
H5AC	0.4413	0.1264	0.7475	0.053*	0.50
C6A	0.4388 (4)	0.2500	0.5616 (4)	0.0281 (13)
H6A	0.4946	0.2500	0.6119	0.034*
N1B	0.0340 (3)	0.2500	0.0507 (3)	0.0271 (11)
H1B	−0.0328 (19)	0.2500	0.055 (4)	0.033*
C2B	0.1056 (4)	0.2500	0.1274 (4)	0.0245 (12)
S21B	0.07768 (11)	0.2500	0.24316 (10)	0.0317 (4)
N3B	0.2032 (4)	0.2500	0.1060 (3)	0.0271 (11)
H3B	0.252 (3)	0.2500	0.155 (3)	0.033*
C4B	0.2344 (4)	0.2500	0.0135 (4)	0.0262 (13)
O41B	0.3242 (3)	0.2500	0.0038 (3)	0.0348 (11)
C5B	0.1509 (4)	0.2500	−0.0646 (4)	0.0262 (12)
O51B	0.1820 (3)	0.2500	−0.1534 (2)	0.0289 (10)
C52B	0.1029 (5)	0.2500	−0.2340 (4)	0.0346 (15)
H5BA	0.1334	0.2500	−0.2949	0.052*
H5BB	0.0606	0.3736	−0.2312	0.052*	0.50
H5BC	0.0606	0.1264	−0.2312	0.052*	0.50
C6B	0.0548 (4)	0.2500	−0.0441 (4)	0.0272 (13)
H6B	0.0002	0.2500	−0.0956	0.033*
C1X	0.7726 (6)	0.2500	0.6700 (4)	0.0525 (19)
H1XA	0.8468	0.2500	0.6866	0.079*	0.668 (12)
H1XB	0.7440	0.1264	0.6971	0.079*	0.334 (6)
H1XC	0.7440	0.3736	0.6971	0.079*	0.334 (6)
H1XD	0.8268	0.2500	0.7250	0.079*	0.332 (12)
H1XE	0.7303	0.1264	0.6729	0.079*	0.166 (6)
H1XF	0.7303	0.3736	0.6729	0.079*	0.166 (6)
O21X	0.6582 (3)	0.2500	0.5152 (3)	0.0462 (13)
C31X	0.8023 (8)	0.2500	0.4064 (4)	0.079 (3)
H3XA	0.8652	0.2500	0.3758	0.119*	0.668 (12)
H3XB	0.7623	0.3736	0.3862	0.119*	0.334 (6)
H3XC	0.7623	0.1264	0.3862	0.119*	0.334 (6)
H3XD	0.8763	0.2500	0.4244	0.119*	0.332 (12)
H3XE	0.7822	0.3736	0.3679	0.119*	0.166 (6)
H3XF	0.7822	0.1264	0.3679	0.119*	0.166 (6)
C32X	0.9290 (4)	0.2500	0.5650 (5)	0.053 (2)
H4XA	0.9788	0.2500	0.5183	0.079*	0.668 (12)
H4XB	0.9387	0.1264	0.6059	0.079*	0.334 (6)
H4XC	0.9387	0.3736	0.6059	0.079*	0.334 (6)
H4XD	0.9697	0.2500	0.6292	0.079*	0.332 (12)
H4XE	0.9450	0.3736	0.5290	0.079*	0.166 (6)
H4XF	0.9450	0.1264	0.5290	0.079*	0.166 (6)
C1Y	−0.2416 (5)	0.2500	0.1663 (4)	0.0428 (16)
H1YA	−0.3113	0.2500	0.1834	0.064*	0.759 (11)
H1YB	−0.2057	0.3736	0.1932	0.064*	0.380 (6)
H1YC	−0.2057	0.1264	0.1932	0.064*	0.380 (6)
H1YD	−0.2807	0.2500	0.2219	0.064*	0.241 (11)
H1YE	−0.1986	0.3736	0.1688	0.064*	0.120 (6)
H1YF	−0.1986	0.1264	0.1688	0.064*	0.120 (6)
O21Y	−0.1696 (3)	0.2500	0.0108 (3)	0.0442 (13)
C31Y	−0.3446 (5)	0.2500	−0.0982 (4)	0.0478 (18)
H3YA	−0.4167	0.2500	−0.1253	0.072*	0.759 (11)
H3YB	−0.3114	0.1264	−0.1202	0.072*	0.380 (6)
H3YC	−0.3114	0.3736	−0.1202	0.072*	0.380 (6)
H3YD	−0.4139	0.2500	−0.0800	0.072*	0.241 (11)
H3YE	−0.3347	0.1264	−0.1367	0.072*	0.120 (6)
H3YF	−0.3347	0.3736	−0.1367	0.072*	0.120 (6)
C32Y	−0.4266 (4)	0.2500	0.0601 (5)	0.054 (2)
H4YA	−0.4880	0.2500	0.0126	0.081*	0.759 (11)
H4YB	−0.4261	0.3736	0.1009	0.081*	0.380 (6)
H4YC	−0.4261	0.1264	0.1009	0.081*	0.380 (6)
H4YD	−0.4517	0.2500	0.1236	0.081*	0.241 (11)
H4YE	−0.4513	0.1264	0.0237	0.081*	0.120 (6)
H4YF	−0.4513	0.3736	0.0237	0.081*	0.120 (6)
C2X	0.7460 (5)	0.2500	0.5592 (5)	0.029 (2)	0.668 (12)
N3X	0.8280 (5)	0.2500	0.5137 (5)	0.034 (2)	0.668 (12)
C2X'	0.7488 (6)	0.2500	0.4993 (7)	0.030 (4)	0.332 (12)
N3X'	0.8189 (6)	0.2500	0.5769 (6)	0.030 (4)	0.332 (12)
C2Y	−0.2447 (5)	0.2500	0.0572 (4)	0.0291 (19)	0.759 (11)
N3Y	−0.3362 (4)	0.2500	0.0089 (4)	0.0337 (19)	0.759 (11)
C2Y'	−0.2670 (7)	0.2500	−0.0058 (7)	0.031 (5)	0.241 (11)
N3Y'	−0.3133 (7)	0.2500	0.0739 (7)	0.034 (5)	0.241 (11)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.018 (2)	0.042 (4)	0.023 (2)	0.000	0.0026 (18)	0.000
C2A	0.024 (3)	0.026 (3)	0.022 (2)	0.000	0.000 (2)	0.000
S21A	0.0232 (7)	0.0454 (11)	0.0232 (6)	0.000	0.0021 (5)	0.000
N3A	0.016 (2)	0.029 (3)	0.024 (2)	0.000	−0.0014 (16)	0.000
C4A	0.023 (3)	0.023 (3)	0.029 (3)	0.000	0.007 (2)	0.000
O41A	0.019 (2)	0.047 (3)	0.035 (2)	0.000	0.0035 (16)	0.000
C5A	0.026 (3)	0.029 (4)	0.020 (2)	0.000	0.001 (2)	0.000
O51A	0.024 (2)	0.049 (3)	0.0233 (17)	0.000	0.0038 (15)	0.000
C52A	0.031 (3)	0.052 (5)	0.021 (2)	0.000	−0.003 (2)	0.000
C6A	0.026 (3)	0.030 (4)	0.026 (3)	0.000	−0.002 (2)	0.000
N1B	0.016 (2)	0.033 (3)	0.032 (2)	0.000	0.0048 (19)	0.000
C2B	0.022 (3)	0.020 (3)	0.030 (3)	0.000	−0.002 (2)	0.000
S21B	0.0230 (7)	0.0439 (11)	0.0277 (7)	0.000	0.0014 (5)	0.000
N3B	0.023 (2)	0.031 (3)	0.027 (2)	0.000	−0.0011 (18)	0.000
C4B	0.023 (3)	0.026 (4)	0.029 (3)	0.000	0.002 (2)	0.000
O41B	0.021 (2)	0.042 (3)	0.041 (2)	0.000	0.0005 (17)	0.000
C5B	0.025 (3)	0.025 (3)	0.028 (3)	0.000	0.003 (2)	0.000
O51B	0.0225 (19)	0.042 (3)	0.0217 (17)	0.000	0.0019 (14)	0.000
C52B	0.029 (3)	0.046 (5)	0.027 (3)	0.000	−0.002 (2)	0.000
C6B	0.020 (3)	0.032 (4)	0.028 (3)	0.000	−0.004 (2)	0.000
C1X	0.088 (6)	0.036 (4)	0.034 (3)	0.000	0.012 (3)	0.000
O21X	0.022 (2)	0.052 (4)	0.061 (3)	0.000	−0.0101 (19)	0.000
C31X	0.160 (9)	0.050 (6)	0.030 (3)	0.000	0.020 (4)	0.000
C32X	0.025 (3)	0.070 (6)	0.062 (4)	0.000	−0.002 (3)	0.000
C1Y	0.059 (4)	0.032 (4)	0.035 (3)	0.000	−0.002 (3)	0.000
O21Y	0.020 (2)	0.058 (4)	0.055 (3)	0.000	0.0060 (18)	0.000
C31Y	0.046 (4)	0.057 (5)	0.035 (3)	0.000	−0.015 (3)	0.000
C32Y	0.028 (3)	0.070 (6)	0.067 (4)	0.000	0.016 (3)	0.000
C2X	0.021 (4)	0.022 (5)	0.044 (5)	0.000	−0.004 (4)	0.000
N3X	0.025 (4)	0.039 (5)	0.036 (4)	0.000	−0.003 (3)	0.000
C2X'	0.030 (6)	0.022 (10)	0.035 (6)	0.000	−0.005 (6)	0.000
N3X'	0.031 (6)	0.030 (9)	0.028 (6)	0.000	−0.006 (5)	0.000
C2Y	0.025 (4)	0.029 (5)	0.032 (4)	0.000	−0.002 (3)	0.000
N3Y	0.018 (3)	0.038 (5)	0.045 (4)	0.000	0.003 (3)	0.000
C2Y'	0.022 (7)	0.036 (13)	0.034 (7)	0.000	0.001 (6)	0.000
N3Y'	0.025 (7)	0.041 (12)	0.037 (7)	0.000	0.006 (6)	0.000

Geometric parameters (Å, º)

N1A—C2A	1.339 (7)	C31X—H3XA	0.9800
N1A—C6A	1.383 (7)	C31X—H3XB	0.9800
N1A—H1A	0.86 (2)	C31X—H3XC	0.9800
C2A—N3A	1.366 (7)	C31X—H3XD	0.9800
C2A—S21A	1.680 (5)	C31X—H3XE	0.9800
N3A—C4A	1.387 (6)	C31X—H3XF	0.9800
N3A—H3A	0.87 (2)	C32X—N3X	1.433 (7)
C4A—O41A	1.222 (6)	C32X—N3X'	1.486 (8)
C4A—C5A	1.458 (8)	C32X—H4XA	0.9800
C5A—C6A	1.329 (8)	C32X—H4XB	0.9800
C5A—O51A	1.355 (6)	C32X—H4XC	0.9800
O51A—C52A	1.437 (7)	C32X—H4XD	0.9801
C52A—H5AA	0.9800	C32X—H4XE	0.9800
C52A—H5AB	0.9800	C32X—H4XF	0.9800
C52A—H5AC	0.9800	C1Y—N3Y'	1.497 (9)
C6A—H6A	0.9500	C1Y—C2Y	1.508 (7)
N1B—C2B	1.334 (7)	C1Y—H1YA	0.9800
N1B—C6B	1.376 (7)	C1Y—H1YB	0.9800
N1B—H1B	0.89 (2)	C1Y—H1YC	0.9800
C2B—N3B	1.360 (7)	C1Y—H1YD	0.9801
C2B—S21B	1.691 (5)	C1Y—H1YE	0.9800
N3B—C4B	1.396 (7)	C1Y—H1YF	0.9800
N3B—H3B	0.87 (2)	O21Y—C2Y	1.249 (6)
C4B—O41B	1.212 (6)	O21Y—C2Y'	1.280 (8)
C4B—C5B	1.447 (8)	C31Y—N3Y	1.476 (7)
C5B—C6B	1.336 (7)	C31Y—C2Y'	1.538 (8)
C5B—O51B	1.346 (6)	C31Y—H3YA	0.9800
O51B—C52B	1.433 (7)	C31Y—H3YB	0.9800
C52B—H5BA	0.9800	C31Y—H3YC	0.9800
C52B—H5BB	0.9800	C31Y—H3YD	0.9799
C52B—H5BC	0.9800	C31Y—H3YE	0.9800
C6B—H6B	0.9500	C31Y—H3YF	0.9800
C1X—N3X'	1.495 (8)	C32Y—N3Y	1.463 (6)
C1X—C2X	1.532 (7)	C32Y—N3Y'	1.486 (8)
C1X—H1XA	0.9800	C32Y—H4YA	0.9800
C1X—H1XB	0.9800	C32Y—H4YB	0.9800
C1X—H1XC	0.9800	C32Y—H4YC	0.9800
C1X—H1XD	0.9800	C32Y—H4YD	0.9800
C1X—H1XE	0.9799	C32Y—H4YE	0.9800
C1X—H1XF	0.9799	C32Y—H4YF	0.9800
O21X—C2X	1.243 (7)	C2X—N3X	1.321 (7)
O21X—C2X'	1.246 (8)	C2X'—N3X'	1.329 (9)
C31X—N3X	1.485 (7)	C2Y—N3Y	1.309 (7)
C31X—C2X'	1.546 (8)	C2Y'—N3Y'	1.328 (9)
C2A—N1A—C6A	123.5 (5)	H3XE—C31X—H3XF	109.5
C2A—N1A—H1A	121 (4)	N3X—C32X—H4XA	109.5
C6A—N1A—H1A	115 (4)	N3X—C32X—H4XB	109.5
N1A—C2A—N3A	114.6 (4)	H4XA—C32X—H4XB	109.5
N1A—C2A—S21A	122.5 (4)	N3X—C32X—H4XC	109.5
N3A—C2A—S21A	122.9 (4)	H4XA—C32X—H4XC	109.5
C2A—N3A—C4A	127.5 (5)	H4XB—C32X—H4XC	109.5
C2A—N3A—H3A	116 (4)	N3X'—C32X—H4XD	109.5
C4A—N3A—H3A	116 (4)	N3X'—C32X—H4XE	109.5
O41A—C4A—N3A	121.0 (5)	H4XD—C32X—H4XE	109.5
O41A—C4A—C5A	125.6 (5)	N3X'—C32X—H4XF	109.5
N3A—C4A—C5A	113.5 (4)	H4XD—C32X—H4XF	109.5
C6A—C5A—O51A	126.7 (5)	H4XE—C32X—H4XF	109.5
C6A—C5A—C4A	119.8 (5)	C2Y—C1Y—H1YA	109.5
O51A—C5A—C4A	113.5 (4)	C2Y—C1Y—H1YB	109.5
C5A—O51A—C52A	114.8 (4)	H1YA—C1Y—H1YB	109.5
O51A—C52A—H5AA	109.5	C2Y—C1Y—H1YC	109.5
O51A—C52A—H5AB	109.5	H1YA—C1Y—H1YC	109.5
H5AA—C52A—H5AB	109.5	H1YB—C1Y—H1YC	109.5
O51A—C52A—H5AC	109.5	N3Y'—C1Y—H1YD	109.5
H5AA—C52A—H5AC	109.5	N3Y'—C1Y—H1YE	109.5
H5AB—C52A—H5AC	109.5	H1YD—C1Y—H1YE	109.5
C5A—C6A—N1A	121.1 (5)	N3Y'—C1Y—H1YF	109.5
C5A—C6A—H6A	119.4	H1YD—C1Y—H1YF	109.5
N1A—C6A—H6A	119.4	H1YE—C1Y—H1YF	109.5
C2B—N1B—C6B	123.8 (5)	N3Y—C31Y—H3YA	109.5
C2B—N1B—H1B	124 (4)	N3Y—C31Y—H3YB	109.5
C6B—N1B—H1B	112 (4)	H3YA—C31Y—H3YB	109.5
N1B—C2B—N3B	115.1 (4)	N3Y—C31Y—H3YC	109.5
N1B—C2B—S21B	122.7 (4)	H3YA—C31Y—H3YC	109.5
N3B—C2B—S21B	122.2 (4)	H3YB—C31Y—H3YC	109.5
C2B—N3B—C4B	126.7 (5)	C2Y'—C31Y—H3YD	109.5
C2B—N3B—H3B	117 (4)	C2Y'—C31Y—H3YE	109.5
C4B—N3B—H3B	116 (4)	H3YD—C31Y—H3YE	109.5
O41B—C4B—N3B	120.5 (5)	C2Y'—C31Y—H3YF	109.5
O41B—C4B—C5B	125.7 (5)	H3YD—C31Y—H3YF	109.5
N3B—C4B—C5B	113.7 (5)	H3YE—C31Y—H3YF	109.5
C6B—C5B—O51B	127.0 (5)	N3Y—C32Y—H4YA	109.5
C6B—C5B—C4B	119.9 (5)	N3Y—C32Y—H4YB	109.5
O51B—C5B—C4B	113.1 (5)	H4YA—C32Y—H4YB	109.5
C5B—O51B—C52B	115.9 (4)	N3Y—C32Y—H4YC	109.5
O51B—C52B—H5BA	109.5	H4YA—C32Y—H4YC	109.5
O51B—C52B—H5BB	109.5	H4YB—C32Y—H4YC	109.5
H5BA—C52B—H5BB	109.5	N3Y'—C32Y—H4YD	109.5
O51B—C52B—H5BC	109.5	N3Y'—C32Y—H4YE	109.5
H5BA—C52B—H5BC	109.5	H4YD—C32Y—H4YE	109.5
H5BB—C52B—H5BC	109.5	N3Y'—C32Y—H4YF	109.5
C5B—C6B—N1B	120.8 (5)	H4YD—C32Y—H4YF	109.5
C5B—C6B—H6B	119.6	H4YE—C32Y—H4YF	109.5
N1B—C6B—H6B	119.6	O21X—C2X—N3X	122.6 (6)
C2X—C1X—H1XA	109.5	O21X—C2X—C1X	125.1 (6)
C2X—C1X—H1XB	109.5	N3X—C2X—C1X	112.3 (6)
H1XA—C1X—H1XB	109.5	C2X—N3X—C32X	122.2 (6)
C2X—C1X—H1XC	109.5	C2X—N3X—C31X	112.3 (6)
H1XA—C1X—H1XC	109.5	C32X—N3X—C31X	125.5 (6)
H1XB—C1X—H1XC	109.5	O21X—C2X'—N3X'	116.5 (8)
N3X'—C1X—H1XD	109.5	O21X—C2X'—C31X	134.2 (9)
N3X'—C1X—H1XE	109.5	N3X'—C2X'—C31X	109.3 (7)
H1XD—C1X—H1XE	109.5	C2X'—N3X'—C32X	120.2 (7)
N3X'—C1X—H1XF	109.5	C2X'—N3X'—C1X	112.3 (7)
H1XD—C1X—H1XF	109.5	C32X—N3X'—C1X	127.5 (7)
H1XE—C1X—H1XF	109.5	O21Y—C2Y—N3Y	118.7 (5)
N3X—C31X—H3XA	109.5	O21Y—C2Y—C1Y	126.4 (5)
N3X—C31X—H3XB	109.5	N3Y—C2Y—C1Y	114.9 (5)
H3XA—C31X—H3XB	109.5	C2Y—N3Y—C32Y	120.7 (6)
N3X—C31X—H3XC	109.5	C2Y—N3Y—C31Y	117.6 (5)
H3XA—C31X—H3XC	109.5	C32Y—N3Y—C31Y	121.6 (5)
H3XB—C31X—H3XC	109.5	O21Y—C2Y'—N3Y'	114.1 (8)
C2X'—C31X—H3XD	109.5	O21Y—C2Y'—C31Y	134.5 (9)
C2X'—C31X—H3XE	109.5	N3Y'—C2Y'—C31Y	111.3 (7)
H3XD—C31X—H3XE	109.5	C2Y'—N3Y'—C32Y	117.0 (7)
C2X'—C31X—H3XF	109.5	C2Y'—N3Y'—C1Y	113.8 (7)
H3XD—C31X—H3XF	109.5	C32Y—N3Y'—C1Y	129.1 (8)
C6A—N1A—C2A—N3A	0.000 (1)	N3X'—C32X—N3X—C31X	180.000 (2)
C6A—N1A—C2A—S21A	180.0	C2X'—C31X—N3X—C2X	0.000 (2)
N1A—C2A—N3A—C4A	0.000 (1)	C2X'—C31X—N3X—C32X	180.000 (2)
S21A—C2A—N3A—C4A	180.0	C2X—O21X—C2X'—N3X'	0.000 (3)
C2A—N3A—C4A—O41A	180.0	C2X—O21X—C2X'—C31X	180.000 (4)
C2A—N3A—C4A—C5A	0.000 (1)	N3X—C31X—C2X'—O21X	180.000 (3)
O41A—C4A—C5A—C6A	180.000 (1)	N3X—C31X—C2X'—N3X'	0.000 (3)
N3A—C4A—C5A—C6A	0.000 (1)	O21X—C2X'—N3X'—C32X	180.000 (2)
O41A—C4A—C5A—O51A	0.000 (1)	C31X—C2X'—N3X'—C32X	0.000 (1)
N3A—C4A—C5A—O51A	180.0	O21X—C2X'—N3X'—C1X	0.000 (2)
C6A—C5A—O51A—C52A	0.000 (2)	C31X—C2X'—N3X'—C1X	180.000 (1)
C4A—C5A—O51A—C52A	180.000 (1)	N3X—C32X—N3X'—C2X'	0.000 (2)
O51A—C5A—C6A—N1A	180.000 (1)	N3X—C32X—N3X'—C1X	180.000 (3)
C4A—C5A—C6A—N1A	0.000 (2)	C2X—C1X—N3X'—C2X'	0.000 (3)
C2A—N1A—C6A—C5A	0.000 (1)	C2X—C1X—N3X'—C32X	180.000 (3)
C6B—N1B—C2B—N3B	0.0	C2Y'—O21Y—C2Y—N3Y	0.0
C6B—N1B—C2B—S21B	180.0	C2Y'—O21Y—C2Y—C1Y	180.0
N1B—C2B—N3B—C4B	0.0	N3Y'—C1Y—C2Y—O21Y	180.0
S21B—C2B—N3B—C4B	180.0	N3Y'—C1Y—C2Y—N3Y	0.0
C2B—N3B—C4B—O41B	180.0	O21Y—C2Y—N3Y—C32Y	180.0
C2B—N3B—C4B—C5B	0.0	C1Y—C2Y—N3Y—C32Y	0.0
O41B—C4B—C5B—C6B	180.0	O21Y—C2Y—N3Y—C31Y	0.0
N3B—C4B—C5B—C6B	0.0	C1Y—C2Y—N3Y—C31Y	180.0
O41B—C4B—C5B—O51B	0.0	N3Y'—C32Y—N3Y—C2Y	0.0
N3B—C4B—C5B—O51B	180.0	N3Y'—C32Y—N3Y—C31Y	180.0
C6B—C5B—O51B—C52B	0.0	C2Y'—C31Y—N3Y—C2Y	0.0
C4B—C5B—O51B—C52B	180.0	C2Y'—C31Y—N3Y—C32Y	180.0
O51B—C5B—C6B—N1B	180.0	C2Y—O21Y—C2Y'—N3Y'	0.0
C4B—C5B—C6B—N1B	0.0	C2Y—O21Y—C2Y'—C31Y	180.0
C2B—N1B—C6B—C5B	0.0	N3Y—C31Y—C2Y'—O21Y	180.0
C2X'—O21X—C2X—N3X	0.000 (2)	N3Y—C31Y—C2Y'—N3Y'	0.0
C2X'—O21X—C2X—C1X	180.000 (2)	O21Y—C2Y'—N3Y'—C32Y	180.0
N3X'—C1X—C2X—O21X	180.000 (3)	C31Y—C2Y'—N3Y'—C32Y	0.0
N3X'—C1X—C2X—N3X	0.000 (2)	O21Y—C2Y'—N3Y'—C1Y	0.0
O21X—C2X—N3X—C32X	180.000 (2)	C31Y—C2Y'—N3Y'—C1Y	180.0
C1X—C2X—N3X—C32X	0.000 (2)	N3Y—C32Y—N3Y'—C2Y'	0.0
O21X—C2X—N3X—C31X	0.000 (2)	N3Y—C32Y—N3Y'—C1Y	180.0
C1X—C2X—N3X—C31X	180.000 (1)	C2Y—C1Y—N3Y'—C2Y'	0.0
N3X'—C32X—N3X—C2X	0.000 (2)	C2Y—C1Y—N3Y'—C32Y	180.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21X	0.86 (2)	1.89 (4)	2.658 (6)	147 (6)
N3A—H3A···S21B	0.87 (2)	2.55 (2)	3.420 (5)	172 (5)
N1B—H1B···O21Y	0.89 (2)	1.84 (3)	2.681 (6)	157 (6)
N3B—H3B···S21A	0.87 (2)	2.49 (2)	3.354 (5)	171 (5)

(III) 5,6-Dimethyl-2-thiouracil

Crystal data

C6H8N2OS	F(000) = 328
Mr = 156.20	Dx = 1.517 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 12075 reflections
a = 6.8295 (10) Å	θ = 3.4–26.1°
b = 15.2624 (18) Å	µ = 0.40 mm^−1
c = 7.0948 (11) Å	T = 173 K
β = 112.336 (11)°	Plate, colourless
V = 684.04 (17) Å^3	0.50 × 0.25 × 0.20 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	1285 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	1212 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.083
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −8→8
Tmin = 0.827, Tmax = 0.925	k = −17→18
5187 measured reflections	l = −8→7

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.057	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.149	w = 1/[σ^2(Fo^2) + (0.0769P)^2 + 0.358P] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max = 0.014
1285 reflections	Δρmax = 0.28 e Å^−3
102 parameters	Δρmin = −0.32 e Å^−3
2 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.060 (17)

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.2157 (3)	0.71481 (14)	0.4273 (3)	0.0454 (5)
H1A	0.085 (3)	0.714 (2)	0.414 (5)	0.062 (9)*
C2A	0.3172 (4)	0.63730 (17)	0.4424 (4)	0.0464 (6)
S21A	0.19292 (10)	0.54215 (4)	0.43357 (11)	0.0523 (4)
N3A	0.5214 (3)	0.64419 (15)	0.4632 (3)	0.0467 (6)
H3A	0.593 (4)	0.5962 (15)	0.478 (5)	0.056 (8)*
C4A	0.6330 (4)	0.72198 (17)	0.4746 (4)	0.0462 (6)
O41A	0.8178 (3)	0.71810 (12)	0.4909 (3)	0.0536 (5)
C5A	0.5161 (4)	0.80172 (17)	0.4663 (4)	0.0466 (6)
C51A	0.6322 (4)	0.88694 (19)	0.4896 (5)	0.0547 (7)
H51A	0.5307	0.9355	0.4557	0.082*
H51B	0.7089	0.8879	0.3976	0.082*
H51C	0.7329	0.8932	0.6307	0.082*
C6A	0.3095 (4)	0.79589 (17)	0.4392 (4)	0.0454 (6)
C61A	0.1667 (4)	0.87236 (18)	0.4199 (4)	0.0513 (7)
H61A	0.2429	0.9175	0.5187	0.077*
H61B	0.0426	0.8533	0.4467	0.077*
H61C	0.1208	0.8964	0.2817	0.077*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0400 (12)	0.0477 (12)	0.0515 (12)	0.0001 (8)	0.0205 (10)	0.0008 (8)
C2A	0.0468 (14)	0.0493 (14)	0.0462 (13)	0.0011 (10)	0.0211 (11)	0.0018 (10)
S21A	0.0480 (5)	0.0470 (5)	0.0659 (5)	−0.0018 (2)	0.0262 (4)	0.0017 (3)
N3A	0.0433 (12)	0.0459 (12)	0.0550 (12)	0.0027 (9)	0.0233 (10)	0.0019 (9)
C4A	0.0444 (14)	0.0479 (14)	0.0480 (13)	−0.0005 (10)	0.0196 (11)	0.0010 (10)
O41A	0.0424 (11)	0.0565 (11)	0.0661 (12)	0.0005 (8)	0.0255 (9)	0.0015 (9)
C5A	0.0452 (14)	0.0478 (14)	0.0492 (13)	−0.0011 (10)	0.0204 (11)	−0.0004 (10)
C51A	0.0468 (14)	0.0507 (15)	0.0689 (17)	−0.0010 (11)	0.0245 (13)	−0.0007 (13)
C6A	0.0450 (14)	0.0491 (14)	0.0436 (12)	0.0001 (10)	0.0184 (11)	0.0004 (10)
C61A	0.0485 (15)	0.0500 (16)	0.0590 (16)	0.0036 (11)	0.0243 (13)	0.0014 (11)

Geometric parameters (Å, º)

N1A—C2A	1.355 (3)	C5A—C6A	1.353 (4)
N1A—C6A	1.381 (3)	C5A—C51A	1.499 (4)
N1A—H1A	0.863 (18)	C51A—H51A	0.9800
C2A—N3A	1.350 (3)	C51A—H51B	0.9800
C2A—S21A	1.671 (3)	C51A—H51C	0.9800
N3A—C4A	1.396 (3)	C6A—C61A	1.494 (4)
N3A—H3A	0.865 (18)	C61A—H61A	0.9800
C4A—O41A	1.224 (3)	C61A—H61B	0.9800
C4A—C5A	1.444 (4)	C61A—H61C	0.9800
C2A—N1A—C6A	124.5 (2)	C5A—C51A—H51A	109.5
C2A—N1A—H1A	119 (2)	C5A—C51A—H51B	109.5
C6A—N1A—H1A	117 (2)	H51A—C51A—H51B	109.5
N3A—C2A—N1A	114.6 (2)	C5A—C51A—H51C	109.5
N3A—C2A—S21A	124.1 (2)	H51A—C51A—H51C	109.5
N1A—C2A—S21A	121.2 (2)	H51B—C51A—H51C	109.5
C2A—N3A—C4A	126.2 (2)	C5A—C6A—N1A	120.1 (2)
C2A—N3A—H3A	117 (2)	C5A—C6A—C61A	124.8 (2)
C4A—N3A—H3A	116 (2)	N1A—C6A—C61A	115.0 (2)
O41A—C4A—N3A	119.0 (2)	C6A—C61A—H61A	109.5
O41A—C4A—C5A	125.3 (2)	C6A—C61A—H61B	109.5
N3A—C4A—C5A	115.7 (2)	H61A—C61A—H61B	109.5
C6A—C5A—C4A	118.7 (2)	C6A—C61A—H61C	109.5
C6A—C5A—C51A	123.5 (2)	H61A—C61A—H61C	109.5
C4A—C5A—C51A	117.8 (2)	H61B—C61A—H61C	109.5
C6A—N1A—C2A—N3A	−2.4 (4)	O41A—C4A—C5A—C51A	−3.2 (4)
C6A—N1A—C2A—S21A	178.05 (19)	N3A—C4A—C5A—C51A	176.7 (2)
N1A—C2A—N3A—C4A	1.5 (4)	C4A—C5A—C6A—N1A	2.3 (4)
S21A—C2A—N3A—C4A	−178.9 (2)	C51A—C5A—C6A—N1A	−177.3 (2)
C2A—N3A—C4A—O41A	−179.1 (2)	C4A—C5A—C6A—C61A	−177.6 (2)
C2A—N3A—C4A—C5A	1.1 (4)	C51A—C5A—C6A—C61A	2.7 (4)
O41A—C4A—C5A—C6A	177.1 (2)	C2A—N1A—C6A—C5A	0.5 (4)
N3A—C4A—C5A—C6A	−3.0 (4)	C2A—N1A—C6A—C61A	−179.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O41A^i	0.86 (2)	2.09 (2)	2.920 (3)	160 (3)
N3A—H3A···S21A^ii	0.87 (2)	2.51 (2)	3.368 (2)	173 (3)

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

(IIIa) 5,6-Dimethyl-2-thiouracil–1-methylpyrrolidin-2-one (1/1)

Crystal data

C6H8N2OS·C5H9NO	F(000) = 1088
Mr = 255.34	Dx = 1.384 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 17691 reflections
a = 15.2437 (6) Å	θ = 3.4–26.1°
b = 6.8275 (17) Å	µ = 0.26 mm^−1
c = 23.555 (2) Å	T = 173 K
V = 2451.5 (7) Å^3	Needle, colourless
Z = 8	0.60 × 0.25 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer	2319 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	2081 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.110
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −18→18
Tmin = 0.860, Tmax = 0.950	k = −8→8
17581 measured reflections	l = −28→28

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ^2(Fo^2) + (0.0453P)^2 + 3.1075P] where P = (Fo^2 + 2Fc^2)/3
2319 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.80170 (12)	0.5026 (3)	0.59190 (8)	0.0177 (4)
H1A	0.809 (2)	0.532 (5)	0.6284 (16)	0.050 (10)*
C2A	0.87471 (14)	0.4924 (3)	0.56032 (10)	0.0178 (5)
S21A	0.97563 (4)	0.51414 (9)	0.58893 (2)	0.0235 (2)
N3A	0.86276 (13)	0.4627 (3)	0.50443 (8)	0.0193 (4)
H3A	0.907 (2)	0.459 (4)	0.4837 (12)	0.024 (7)*
C4A	0.78201 (15)	0.4458 (3)	0.47674 (9)	0.0202 (5)
O41A	0.78102 (12)	0.4195 (3)	0.42561 (7)	0.0308 (4)
C5A	0.70610 (14)	0.4616 (3)	0.51321 (10)	0.0195 (5)
C51A	0.61767 (16)	0.4481 (4)	0.48523 (11)	0.0277 (5)
H51A	0.5736	0.4096	0.5134	0.042*
H51B	0.6197	0.3501	0.4549	0.042*
H51C	0.6020	0.5758	0.4692	0.042*
C6A	0.71791 (14)	0.4883 (3)	0.56952 (9)	0.0172 (5)
C61A	0.64583 (15)	0.5045 (4)	0.61232 (10)	0.0231 (5)
H61A	0.6113	0.6226	0.6048	0.035*
H61B	0.6711	0.5123	0.6505	0.035*
H61C	0.6078	0.3890	0.6098	0.035*
N1X	0.86658 (13)	0.6219 (3)	0.79225 (8)	0.0234 (4)
C11X	0.82548 (19)	0.7986 (4)	0.81222 (12)	0.0349 (6)
H11A	0.8012	0.8710	0.7799	0.052*
H11B	0.8690	0.8799	0.8317	0.052*
H11C	0.7781	0.7652	0.8386	0.052*
C2X	0.85453 (15)	0.5458 (4)	0.74101 (9)	0.0213 (5)
O21X	0.80889 (11)	0.6194 (3)	0.70333 (7)	0.0262 (4)
C3X	0.90259 (17)	0.3541 (4)	0.73741 (10)	0.0274 (5)
H3X1	0.9371	0.3454	0.7019	0.033*
H3X2	0.8612	0.2424	0.7391	0.033*
C4X	0.9627 (2)	0.3563 (5)	0.78924 (12)	0.0383 (7)
H4X1	1.0218	0.4054	0.7792	0.046*
H4X2	0.9683	0.2237	0.8059	0.046*
C5X	0.91651 (17)	0.4958 (4)	0.83033 (10)	0.0309 (6)
H5X1	0.8773	0.4236	0.8565	0.037*
H5X2	0.9594	0.5722	0.8528	0.037*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0165 (10)	0.0230 (10)	0.0137 (9)	0.0001 (7)	0.0000 (7)	0.0004 (7)
C2A	0.0175 (11)	0.0171 (11)	0.0188 (11)	0.0002 (8)	0.0010 (8)	0.0013 (8)
S21A	0.0143 (3)	0.0376 (4)	0.0186 (3)	−0.0006 (2)	−0.0008 (2)	−0.0007 (2)
N3A	0.0153 (9)	0.0266 (10)	0.0159 (9)	−0.0022 (7)	0.0020 (7)	−0.0009 (8)
C4A	0.0212 (11)	0.0202 (11)	0.0191 (11)	−0.0030 (9)	−0.0038 (8)	0.0010 (9)
O41A	0.0311 (9)	0.0459 (11)	0.0154 (8)	−0.0056 (8)	−0.0020 (7)	−0.0034 (7)
C5A	0.0173 (11)	0.0191 (11)	0.0221 (11)	−0.0012 (8)	−0.0021 (9)	0.0021 (9)
C51A	0.0206 (12)	0.0360 (14)	0.0265 (12)	−0.0030 (10)	−0.0065 (9)	0.0043 (11)
C6A	0.0153 (10)	0.0147 (10)	0.0216 (11)	0.0010 (8)	0.0004 (8)	0.0019 (8)
C61A	0.0184 (11)	0.0269 (12)	0.0241 (12)	0.0011 (9)	0.0034 (9)	0.0002 (9)
N1X	0.0221 (10)	0.0315 (11)	0.0165 (9)	0.0005 (8)	−0.0014 (7)	−0.0024 (8)
C11X	0.0364 (14)	0.0386 (15)	0.0296 (13)	0.0050 (12)	−0.0006 (11)	−0.0094 (12)
C2X	0.0173 (10)	0.0290 (12)	0.0176 (11)	−0.0041 (9)	0.0020 (9)	0.0009 (9)
O21X	0.0252 (9)	0.0360 (10)	0.0173 (8)	0.0035 (7)	−0.0031 (6)	0.0009 (7)
C3X	0.0336 (13)	0.0277 (13)	0.0210 (12)	0.0022 (10)	0.0011 (10)	0.0005 (10)
C4X	0.0437 (16)	0.0431 (16)	0.0281 (13)	0.0154 (13)	−0.0055 (12)	0.0036 (12)
C5X	0.0292 (13)	0.0439 (15)	0.0194 (12)	0.0028 (11)	−0.0054 (10)	0.0014 (11)

Geometric parameters (Å, º)

N1A—C2A	1.340 (3)	C61A—H61C	0.9800
N1A—C6A	1.385 (3)	N1X—C2X	1.327 (3)
N1A—H1A	0.89 (4)	N1X—C11X	1.438 (3)
C2A—N3A	1.345 (3)	N1X—C5X	1.458 (3)
C2A—S21A	1.686 (2)	C11X—H11A	0.9800
N3A—C4A	1.398 (3)	C11X—H11B	0.9800
N3A—H3A	0.84 (3)	C11X—H11C	0.9800
C4A—O41A	1.218 (3)	C2X—O21X	1.235 (3)
C4A—C5A	1.445 (3)	C2X—C3X	1.502 (3)
C5A—C6A	1.351 (3)	C3X—C4X	1.526 (4)
C5A—C51A	1.503 (3)	C3X—H3X1	0.9900
C51A—H51A	0.9800	C3X—H3X2	0.9900
C51A—H51B	0.9800	C4X—C5X	1.529 (4)
C51A—H51C	0.9800	C4X—H4X1	0.9900
C6A—C61A	1.495 (3)	C4X—H4X2	0.9900
C61A—H61A	0.9800	C5X—H5X1	0.9900
C61A—H61B	0.9800	C5X—H5X2	0.9900
C2A—N1A—C6A	123.42 (19)	C2X—N1X—C11X	124.4 (2)
C2A—N1A—H1A	116 (2)	C2X—N1X—C5X	113.6 (2)
C6A—N1A—H1A	120 (2)	C11X—N1X—C5X	121.4 (2)
N1A—C2A—N3A	116.0 (2)	N1X—C11X—H11A	109.5
N1A—C2A—S21A	122.08 (17)	N1X—C11X—H11B	109.5
N3A—C2A—S21A	121.89 (17)	H11A—C11X—H11B	109.5
C2A—N3A—C4A	126.1 (2)	N1X—C11X—H11C	109.5
C2A—N3A—H3A	118 (2)	H11A—C11X—H11C	109.5
C4A—N3A—H3A	116 (2)	H11B—C11X—H11C	109.5
O41A—C4A—N3A	119.0 (2)	O21X—C2X—N1X	124.9 (2)
O41A—C4A—C5A	126.1 (2)	O21X—C2X—C3X	126.1 (2)
N3A—C4A—C5A	114.93 (19)	N1X—C2X—C3X	109.0 (2)
C6A—C5A—C4A	119.1 (2)	C2X—C3X—C4X	103.8 (2)
C6A—C5A—C51A	123.9 (2)	C2X—C3X—H3X1	111.0
C4A—C5A—C51A	116.9 (2)	C4X—C3X—H3X1	111.0
C5A—C51A—H51A	109.5	C2X—C3X—H3X2	111.0
C5A—C51A—H51B	109.5	C4X—C3X—H3X2	111.0
H51A—C51A—H51B	109.5	H3X1—C3X—H3X2	109.0
C5A—C51A—H51C	109.5	C3X—C4X—C5X	103.7 (2)
H51A—C51A—H51C	109.5	C3X—C4X—H4X1	111.0
H51B—C51A—H51C	109.5	C5X—C4X—H4X1	111.0
C5A—C6A—N1A	120.4 (2)	C3X—C4X—H4X2	111.0
C5A—C6A—C61A	125.0 (2)	C5X—C4X—H4X2	111.0
N1A—C6A—C61A	114.57 (19)	H4X1—C4X—H4X2	109.0
C6A—C61A—H61A	109.5	N1X—C5X—C4X	102.6 (2)
C6A—C61A—H61B	109.5	N1X—C5X—H5X1	111.2
H61A—C61A—H61B	109.5	C4X—C5X—H5X1	111.2
C6A—C61A—H61C	109.5	N1X—C5X—H5X2	111.2
H61A—C61A—H61C	109.5	C4X—C5X—H5X2	111.2
H61B—C61A—H61C	109.5	H5X1—C5X—H5X2	109.2
C6A—N1A—C2A—N3A	−1.4 (3)	C51A—C5A—C6A—C61A	1.3 (4)
C6A—N1A—C2A—S21A	178.98 (16)	C2A—N1A—C6A—C5A	0.4 (3)
N1A—C2A—N3A—C4A	1.4 (3)	C2A—N1A—C6A—C61A	−179.7 (2)
S21A—C2A—N3A—C4A	−179.00 (18)	C11X—N1X—C2X—O21X	2.4 (4)
C2A—N3A—C4A—O41A	179.8 (2)	C5X—N1X—C2X—O21X	174.3 (2)
C2A—N3A—C4A—C5A	−0.3 (3)	C11X—N1X—C2X—C3X	−175.7 (2)
O41A—C4A—C5A—C6A	179.1 (2)	C5X—N1X—C2X—C3X	−3.7 (3)
N3A—C4A—C5A—C6A	−0.7 (3)	O21X—C2X—C3X—C4X	168.3 (2)
O41A—C4A—C5A—C51A	−1.2 (4)	N1X—C2X—C3X—C4X	−13.7 (3)
N3A—C4A—C5A—C51A	178.9 (2)	C2X—C3X—C4X—C5X	24.4 (3)
C4A—C5A—C6A—N1A	0.7 (3)	C2X—N1X—C5X—C4X	19.4 (3)
C51A—C5A—C6A—N1A	−178.9 (2)	C11X—N1X—C5X—C4X	−168.4 (2)
C4A—C5A—C6A—C61A	−179.1 (2)	C3X—C4X—C5X—N1X	−26.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21X	0.89 (4)	1.86 (4)	2.745 (2)	171 (3)
N3A—H3A···S21A^i	0.84 (3)	2.48 (3)	3.306 (2)	170 (3)

Symmetry code: (i) −x+2, −y+1, −z+1.

(IIIb) 5,6-Dimethyl-2-thiouracil–dimethylformamide (2/1)

Crystal data

2C6H8N2OS·C3H7NO	Z = 2
Mr = 385.50	F(000) = 408
Triclinic, P1	Dx = 1.346 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5895 (13) Å	Cell parameters from 12306 reflections
b = 8.6241 (14) Å	θ = 3.4–26.1°
c = 15.350 (2) Å	µ = 0.30 mm^−1
α = 100.404 (13)°	T = 173 K
β = 95.341 (12)°	Plate, colourless
γ = 119.496 (11)°	0.45 × 0.35 × 0.25 mm
V = 951.2 (3) Å^3

Data collection

Stoe IPDS II two-circle diffractometer	3558 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	3064 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.051
ω scans	θmax = 25.8°, θmin = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→10
Tmin = 0.875, Tmax = 0.928	k = −10→10
7421 measured reflections	l = −16→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0607P)^2 + 0.5125P] where P = (Fo^2 + 2Fc^2)/3
3558 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.3943 (2)	0.0554 (2)	0.57837 (12)	0.0240 (4)
H1A	0.486 (4)	0.143 (4)	0.6124 (18)	0.029*
C2A	0.3457 (3)	−0.1070 (3)	0.59750 (14)	0.0237 (4)
S21A	0.45997 (7)	−0.12608 (7)	0.68532 (4)	0.02876 (16)
N3A	0.1937 (2)	−0.2558 (2)	0.54088 (12)	0.0246 (4)
H3A	0.153 (3)	−0.364 (4)	0.5538 (17)	0.030*
C4A	0.0897 (3)	−0.2538 (3)	0.46699 (14)	0.0250 (4)
O41A	−0.0482 (2)	−0.3984 (2)	0.42258 (11)	0.0323 (4)
C5A	0.1511 (3)	−0.0758 (3)	0.44965 (14)	0.0247 (4)
C51A	0.0431 (3)	−0.0661 (3)	0.37054 (16)	0.0314 (5)
H51A	−0.0051	0.0124	0.3921	0.047*
H51B	−0.0587	−0.1905	0.3389	0.047*
H51C	0.1226	−0.0139	0.3289	0.047*
C6A	0.2999 (3)	0.0740 (3)	0.50726 (14)	0.0241 (4)
C61A	0.3715 (3)	0.2682 (3)	0.50221 (16)	0.0304 (5)
H61A	0.3507	0.2703	0.4387	0.046*
H61B	0.5030	0.3431	0.5288	0.046*
H61C	0.3078	0.3186	0.5358	0.046*
N1B	1.0748 (3)	0.4922 (2)	0.88973 (13)	0.0281 (4)
H1B	1.151 (4)	0.514 (4)	0.935 (2)	0.034*
C2B	0.9367 (3)	0.3165 (3)	0.85468 (15)	0.0275 (4)
S21B	0.91797 (8)	0.14167 (8)	0.89440 (4)	0.03553 (18)
N3B	0.8139 (2)	0.2908 (3)	0.78298 (12)	0.0273 (4)
H3B	0.723 (4)	0.177 (4)	0.7581 (18)	0.033*
C4B	0.8216 (3)	0.4249 (3)	0.74337 (14)	0.0256 (4)
O41B	0.7010 (2)	0.3807 (2)	0.67621 (11)	0.0313 (4)
C5B	0.9722 (3)	0.6086 (3)	0.78350 (14)	0.0256 (4)
C51B	0.9870 (3)	0.7594 (3)	0.74328 (17)	0.0334 (5)
H51D	0.9473	0.8315	0.7815	0.050*
H51E	0.9089	0.7056	0.6823	0.050*
H51F	1.1144	0.8400	0.7396	0.050*
C6B	1.0951 (3)	0.6373 (3)	0.85639 (14)	0.0271 (4)
C61B	1.2603 (3)	0.8221 (3)	0.90410 (16)	0.0359 (5)
H61D	1.3406	0.8680	0.8618	0.054*
H61E	1.3267	0.8100	0.9554	0.054*
H61F	1.2218	0.9090	0.9263	0.054*
C1X	1.3533 (3)	0.4763 (3)	1.07379 (16)	0.0345 (5)
H1X	1.2663	0.3477	1.0524	0.041*
O11X	1.3421 (3)	0.5790 (3)	1.03053 (12)	0.0458 (4)
N2X	1.4782 (2)	0.5334 (3)	1.14775 (13)	0.0294 (4)
C3X	1.4884 (4)	0.4072 (4)	1.1959 (2)	0.0457 (6)
H3X1	1.3905	0.2805	1.1649	0.068*
H3X2	1.4741	0.4386	1.2581	0.068*
H3X3	1.6074	0.4173	1.1972	0.068*
C4X	1.6158 (3)	0.7279 (3)	1.18198 (18)	0.0396 (6)
H4X1	1.7304	0.7513	1.1641	0.059*
H4X2	1.6363	0.7632	1.2482	0.059*
H4X3	1.5737	0.8007	1.1567	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0235 (9)	0.0204 (8)	0.0221 (9)	0.0076 (7)	0.0007 (7)	0.0060 (7)
C2A	0.0239 (10)	0.0225 (9)	0.0241 (10)	0.0113 (8)	0.0055 (8)	0.0065 (8)
S21A	0.0281 (3)	0.0253 (3)	0.0285 (3)	0.0106 (2)	−0.0014 (2)	0.0109 (2)
N3A	0.0248 (9)	0.0194 (8)	0.0256 (9)	0.0082 (7)	0.0009 (7)	0.0092 (7)
C4A	0.0245 (10)	0.0251 (10)	0.0253 (10)	0.0127 (9)	0.0044 (8)	0.0072 (8)
O41A	0.0285 (8)	0.0250 (7)	0.0328 (8)	0.0079 (6)	−0.0040 (6)	0.0081 (6)
C5A	0.0263 (10)	0.0264 (10)	0.0237 (10)	0.0143 (8)	0.0057 (8)	0.0096 (8)
C51A	0.0335 (11)	0.0306 (11)	0.0292 (11)	0.0157 (9)	0.0009 (9)	0.0119 (9)
C6A	0.0259 (10)	0.0243 (10)	0.0248 (10)	0.0138 (8)	0.0077 (8)	0.0089 (8)
C61A	0.0349 (11)	0.0233 (10)	0.0300 (11)	0.0132 (9)	0.0024 (9)	0.0091 (8)
N1B	0.0270 (9)	0.0281 (9)	0.0242 (9)	0.0112 (8)	0.0002 (7)	0.0077 (7)
C2B	0.0279 (10)	0.0300 (11)	0.0260 (11)	0.0156 (9)	0.0073 (9)	0.0077 (9)
S21B	0.0408 (3)	0.0306 (3)	0.0361 (3)	0.0177 (3)	0.0058 (2)	0.0145 (2)
N3B	0.0261 (9)	0.0218 (9)	0.0282 (10)	0.0092 (8)	0.0015 (7)	0.0058 (7)
C4B	0.0255 (10)	0.0273 (10)	0.0252 (10)	0.0144 (9)	0.0063 (8)	0.0068 (8)
O41B	0.0291 (8)	0.0273 (8)	0.0310 (8)	0.0113 (6)	−0.0010 (7)	0.0069 (6)
C5B	0.0278 (10)	0.0244 (10)	0.0246 (10)	0.0126 (9)	0.0078 (8)	0.0083 (8)
C51B	0.0322 (11)	0.0279 (11)	0.0372 (13)	0.0129 (9)	0.0039 (9)	0.0120 (9)
C6B	0.0276 (10)	0.0265 (10)	0.0234 (10)	0.0117 (9)	0.0060 (8)	0.0050 (8)
C61B	0.0337 (12)	0.0281 (11)	0.0312 (12)	0.0066 (10)	0.0030 (10)	0.0059 (9)
C1X	0.0326 (12)	0.0309 (11)	0.0335 (12)	0.0139 (10)	0.0049 (10)	0.0033 (9)
O11X	0.0448 (10)	0.0487 (10)	0.0369 (10)	0.0209 (9)	−0.0062 (8)	0.0133 (8)
N2X	0.0313 (9)	0.0284 (9)	0.0298 (10)	0.0161 (8)	0.0043 (8)	0.0101 (7)
C3X	0.0516 (15)	0.0488 (15)	0.0550 (17)	0.0335 (13)	0.0163 (13)	0.0294 (13)
C4X	0.0326 (12)	0.0347 (13)	0.0399 (14)	0.0118 (10)	−0.0025 (10)	0.0064 (10)

Geometric parameters (Å, º)

N1A—C2A	1.348 (3)	N3B—H3B	0.88 (3)
N1A—C6A	1.379 (3)	C4B—O41B	1.246 (3)
N1A—H1A	0.81 (3)	C4B—C5B	1.429 (3)
C2A—N3A	1.357 (3)	C5B—C6B	1.361 (3)
C2A—S21A	1.674 (2)	C5B—C51B	1.493 (3)
N3A—C4A	1.386 (3)	C51B—H51D	0.9800
N3A—H3A	0.89 (3)	C51B—H51E	0.9800
C4A—O41A	1.229 (3)	C51B—H51F	0.9800
C4A—C5A	1.443 (3)	C6B—C61B	1.499 (3)
C5A—C6A	1.355 (3)	C61B—H61D	0.9800
C5A—C51A	1.498 (3)	C61B—H61E	0.9800
C51A—H51A	0.9800	C61B—H61F	0.9800
C51A—H51B	0.9800	C1X—O11X	1.232 (3)
C51A—H51C	0.9800	C1X—N2X	1.316 (3)
C6A—C61A	1.493 (3)	C1X—H1X	0.9500
C61A—H61A	0.9800	N2X—C4X	1.449 (3)
C61A—H61B	0.9800	N2X—C3X	1.453 (3)
C61A—H61C	0.9800	C3X—H3X1	0.9800
N1B—C2B	1.345 (3)	C3X—H3X2	0.9800
N1B—C6B	1.375 (3)	C3X—H3X3	0.9800
N1B—H1B	0.84 (3)	C4X—H4X1	0.9800
C2B—N3B	1.356 (3)	C4X—H4X2	0.9800
C2B—S21B	1.668 (2)	C4X—H4X3	0.9800
N3B—C4B	1.378 (3)
C2A—N1A—C6A	123.94 (18)	O41B—C4B—N3B	119.33 (19)
C2A—N1A—H1A	114.1 (19)	O41B—C4B—C5B	124.5 (2)
C6A—N1A—H1A	122.0 (19)	N3B—C4B—C5B	116.22 (19)
N1A—C2A—N3A	115.03 (18)	C6B—C5B—C4B	118.34 (19)
N1A—C2A—S21A	123.19 (16)	C6B—C5B—C51B	123.2 (2)
N3A—C2A—S21A	121.77 (15)	C4B—C5B—C51B	118.42 (19)
C2A—N3A—C4A	125.99 (17)	C5B—C51B—H51D	109.5
C2A—N3A—H3A	117.5 (16)	C5B—C51B—H51E	109.5
C4A—N3A—H3A	116.4 (16)	H51D—C51B—H51E	109.5
O41A—C4A—N3A	119.38 (18)	C5B—C51B—H51F	109.5
O41A—C4A—C5A	124.55 (19)	H51D—C51B—H51F	109.5
N3A—C4A—C5A	116.04 (18)	H51E—C51B—H51F	109.5
C6A—C5A—C4A	118.26 (19)	C5B—C6B—N1B	120.45 (19)
C6A—C5A—C51A	123.58 (19)	C5B—C6B—C61B	123.9 (2)
C4A—C5A—C51A	118.13 (19)	N1B—C6B—C61B	115.66 (19)
C5A—C51A—H51A	109.5	C6B—C61B—H61D	109.5
C5A—C51A—H51B	109.5	C6B—C61B—H61E	109.5
H51A—C51A—H51B	109.5	H61D—C61B—H61E	109.5
C5A—C51A—H51C	109.5	C6B—C61B—H61F	109.5
H51A—C51A—H51C	109.5	H61D—C61B—H61F	109.5
H51B—C51A—H51C	109.5	H61E—C61B—H61F	109.5
C5A—C6A—N1A	120.69 (18)	O11X—C1X—N2X	124.2 (2)
C5A—C6A—C61A	124.47 (19)	O11X—C1X—H1X	117.9
N1A—C6A—C61A	114.81 (18)	N2X—C1X—H1X	117.9
C6A—C61A—H61A	109.5	C1X—N2X—C4X	119.8 (2)
C6A—C61A—H61B	109.5	C1X—N2X—C3X	122.4 (2)
H61A—C61A—H61B	109.5	C4X—N2X—C3X	117.7 (2)
C6A—C61A—H61C	109.5	N2X—C3X—H3X1	109.5
H61A—C61A—H61C	109.5	N2X—C3X—H3X2	109.5
H61B—C61A—H61C	109.5	H3X1—C3X—H3X2	109.5
C2B—N1B—C6B	124.0 (2)	N2X—C3X—H3X3	109.5
C2B—N1B—H1B	117.6 (19)	H3X1—C3X—H3X3	109.5
C6B—N1B—H1B	118.5 (19)	H3X2—C3X—H3X3	109.5
N1B—C2B—N3B	114.82 (19)	N2X—C4X—H4X1	109.5
N1B—C2B—S21B	123.14 (17)	N2X—C4X—H4X2	109.5
N3B—C2B—S21B	122.04 (17)	H4X1—C4X—H4X2	109.5
C2B—N3B—C4B	126.21 (19)	N2X—C4X—H4X3	109.5
C2B—N3B—H3B	117.2 (18)	H4X1—C4X—H4X3	109.5
C4B—N3B—H3B	116.6 (18)	H4X2—C4X—H4X3	109.5
C6A—N1A—C2A—N3A	0.1 (3)	C6B—N1B—C2B—S21B	178.21 (16)
C6A—N1A—C2A—S21A	−178.86 (16)	N1B—C2B—N3B—C4B	1.6 (3)
N1A—C2A—N3A—C4A	0.7 (3)	S21B—C2B—N3B—C4B	−177.39 (17)
S21A—C2A—N3A—C4A	179.62 (16)	C2B—N3B—C4B—O41B	178.4 (2)
C2A—N3A—C4A—O41A	−178.0 (2)	C2B—N3B—C4B—C5B	−1.3 (3)
C2A—N3A—C4A—C5A	0.2 (3)	O41B—C4B—C5B—C6B	−179.5 (2)
O41A—C4A—C5A—C6A	176.3 (2)	N3B—C4B—C5B—C6B	0.2 (3)
N3A—C4A—C5A—C6A	−1.8 (3)	O41B—C4B—C5B—C51B	0.4 (3)
O41A—C4A—C5A—C51A	−1.8 (3)	N3B—C4B—C5B—C51B	−179.92 (19)
N3A—C4A—C5A—C51A	−179.94 (18)	C4B—C5B—C6B—N1B	0.5 (3)
C4A—C5A—C6A—N1A	2.6 (3)	C51B—C5B—C6B—N1B	−179.4 (2)
C51A—C5A—C6A—N1A	−179.41 (19)	C4B—C5B—C6B—C61B	179.1 (2)
C4A—C5A—C6A—C61A	−175.4 (2)	C51B—C5B—C6B—C61B	−0.8 (3)
C51A—C5A—C6A—C61A	2.6 (3)	C2B—N1B—C6B—C5B	−0.2 (3)
C2A—N1A—C6A—C5A	−1.7 (3)	C2B—N1B—C6B—C61B	−178.9 (2)
C2A—N1A—C6A—C61A	176.38 (19)	O11X—C1X—N2X—C4X	−1.1 (4)
C6B—N1B—C2B—N3B	−0.8 (3)	O11X—C1X—N2X—C3X	−179.0 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O41B	0.81 (3)	1.95 (3)	2.744 (2)	168 (3)
N3A—H3A···O41A^i	0.89 (3)	1.91 (3)	2.799 (2)	176 (2)
N1B—H1B···O11X	0.84 (3)	1.87 (3)	2.702 (3)	173 (3)
N3B—H3B···S21A	0.88 (3)	2.42 (3)	3.295 (2)	176 (2)

Symmetry code: (i) −x, −y−1, −z+1.

(IIIc) 5,6-Dimethyl2-thiouracil–dimethylacetamide (2/1)

Crystal data

2C6H8N2OS·C4H9NO	Z = 2
Mr = 399.53	F(000) = 424
Triclinic, P1	Dx = 1.362 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0876 (14) Å	Cell parameters from 10760 reflections
b = 11.1034 (17) Å	θ = 3.6–26.3°
c = 11.9115 (17) Å	µ = 0.30 mm^−1
α = 80.017 (12)°	T = 173 K
β = 70.979 (12)°	Plate, colourless
γ = 75.575 (13)°	0.38 × 0.24 × 0.22 mm
V = 974.4 (3) Å^3

Data collection

Stoe IPDS II two-circle diffractometer	3730 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	3106 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.037
ω scans	θmax = 25.9°, θmin = 3.6°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→9
Tmin = 0.895, Tmax = 0.937	k = −13→13
7639 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0559P)^2 + 0.1516P] where P = (Fo^2 + 2Fc^2)/3
3730 reflections	(Δ/σ)max = 0.001
313 parameters	Δρmax = 0.25 e Å^−3
26 restraints	Δρmin = −0.21 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will bde even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.3340 (2)	0.66207 (13)	0.58902 (11)	0.0249 (3)
H1A	0.297 (3)	0.5985 (17)	0.5767 (17)	0.030*
C2A	0.3754 (2)	0.75101 (15)	0.49813 (14)	0.0242 (3)
S21A	0.36922 (7)	0.74289 (4)	0.36059 (3)	0.03193 (13)
N3A	0.42024 (19)	0.84895 (13)	0.52663 (11)	0.0244 (3)
H3A	0.455 (3)	0.9058 (17)	0.4683 (15)	0.029*
C4A	0.4291 (2)	0.86311 (15)	0.63825 (13)	0.0236 (3)
O41A	0.47355 (17)	0.95690 (11)	0.65117 (10)	0.0295 (3)
C5A	0.3834 (2)	0.76446 (15)	0.73080 (13)	0.0236 (3)
C51A	0.3892 (3)	0.77448 (17)	0.85373 (14)	0.0311 (4)
H51A	0.2680	0.7838	0.9094	0.047*	0.70 (2)
H51B	0.4381	0.8474	0.8520	0.047*	0.70 (2)
H51C	0.4653	0.6987	0.8800	0.047*	0.70 (2)
H51D	0.3199	0.8561	0.8795	0.047*	0.30 (2)
H51E	0.5135	0.7658	0.8522	0.047*	0.30 (2)
H51F	0.3380	0.7081	0.9096	0.047*	0.30 (2)
C6A	0.3366 (2)	0.66689 (15)	0.70329 (13)	0.0234 (3)
C61A	0.2851 (3)	0.55836 (16)	0.78930 (14)	0.0302 (4)
H61A	0.3675	0.5306	0.8378	0.045*
H61B	0.2908	0.4898	0.7453	0.045*
H61C	0.1630	0.5833	0.8414	0.045*
N1B	0.1510 (2)	0.32800 (13)	0.29838 (12)	0.0263 (3)
H1B	0.134 (3)	0.2957 (19)	0.2435 (16)	0.032*
C2B	0.1999 (2)	0.43911 (15)	0.27638 (14)	0.0254 (3)
S21B	0.23463 (7)	0.52253 (4)	0.14379 (4)	0.03505 (14)
N3B	0.22123 (19)	0.47809 (13)	0.37228 (11)	0.0246 (3)
H3B	0.254 (3)	0.5476 (16)	0.3609 (17)	0.030*
C4B	0.1970 (2)	0.41463 (15)	0.48489 (13)	0.0244 (3)
O41B	0.21867 (18)	0.46152 (12)	0.56460 (10)	0.0310 (3)
C5B	0.1465 (2)	0.29637 (15)	0.50123 (13)	0.0244 (3)
C51B	0.1225 (3)	0.22574 (17)	0.62268 (15)	0.0323 (4)
H52A	0.0139	0.2680	0.6789	0.048*	0.58 (2)
H52B	0.2261	0.2225	0.6495	0.048*	0.58 (2)
H52C	0.1120	0.1406	0.6191	0.048*	0.58 (2)
H52D	0.2223	0.1538	0.6199	0.048*	0.42 (2)
H52E	0.0099	0.1965	0.6480	0.048*	0.42 (2)
H52F	0.1197	0.2807	0.6796	0.048*	0.42 (2)
C6B	0.1247 (2)	0.25629 (15)	0.40680 (14)	0.0258 (3)
C61B	0.0766 (3)	0.13378 (16)	0.41013 (15)	0.0323 (4)
H61D	0.1856	0.0684	0.3928	0.049*
H61E	0.0150	0.1399	0.3502	0.049*
H61F	−0.0023	0.1128	0.4895	0.049*
C1X	0.178 (2)	0.2769 (15)	−0.0556 (14)	0.044 (3)	0.50
H1X1	0.0820	0.3131	−0.0923	0.066*	0.50
H1X2	0.2848	0.2383	−0.1156	0.066*	0.50
H1X3	0.2057	0.3428	−0.0239	0.066*	0.50
C2X	0.1186 (7)	0.1794 (4)	0.0443 (4)	0.0289 (8)	0.50
O21X	0.119 (2)	0.1867 (19)	0.1479 (11)	0.038 (3)	0.50
N3X	0.0769 (4)	0.0812 (3)	0.0174 (2)	0.0288 (6)	0.50
C31X	0.0193 (6)	−0.0165 (4)	0.1115 (3)	0.0374 (9)	0.50
H31A	0.0513	−0.0089	0.1822	0.056*	0.50
H31B	0.0786	−0.0987	0.0833	0.056*	0.50
H31C	−0.1105	−0.0072	0.1322	0.056*	0.50
C32X	0.0686 (6)	0.0729 (4)	−0.1012 (3)	0.0358 (8)	0.50
H32A	−0.0169	0.1453	−0.1232	0.054*	0.50
H32B	0.0300	−0.0040	−0.1013	0.054*	0.50
H32C	0.1872	0.0718	−0.1590	0.054*	0.50
C1Y	0.221 (2)	0.2818 (13)	−0.0646 (12)	0.045 (3)	0.50
H1Y1	0.1059	0.3407	−0.0476	0.067*	0.50
H1Y2	0.2442	0.2462	−0.1393	0.067*	0.50
H1Y3	0.3164	0.3257	−0.0724	0.067*	0.50
C2Y	0.2183 (7)	0.1795 (3)	0.0350 (3)	0.0278 (8)	0.50
O21Y	0.0942 (17)	0.1934 (17)	0.1297 (9)	0.0300 (17)	0.50
N3Y	0.3485 (4)	0.0775 (3)	0.0188 (2)	0.0291 (6)	0.50
C31Y	0.3569 (6)	−0.0213 (3)	0.1158 (3)	0.0359 (8)	0.50
H31D	0.4489	−0.0154	0.1503	0.054*	0.50
H31E	0.3866	−0.1028	0.0849	0.054*	0.50
H31F	0.2407	−0.0122	0.1774	0.054*	0.50
C32Y	0.5033 (6)	0.0665 (4)	−0.0892 (3)	0.0398 (9)	0.50
H32D	0.4624	0.0714	−0.1590	0.060*	0.50
H32E	0.5853	−0.0139	−0.0816	0.060*	0.50
H32F	0.5655	0.1346	−0.0988	0.060*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0336 (8)	0.0209 (7)	0.0230 (6)	−0.0106 (6)	−0.0098 (5)	0.0007 (5)
C2A	0.0250 (8)	0.0232 (8)	0.0239 (7)	−0.0067 (7)	−0.0068 (6)	0.0005 (6)
S21A	0.0485 (3)	0.0313 (2)	0.0215 (2)	−0.0180 (2)	−0.01356 (17)	0.00338 (16)
N3A	0.0298 (8)	0.0227 (7)	0.0221 (6)	−0.0098 (6)	−0.0086 (5)	0.0027 (5)
C4A	0.0226 (8)	0.0228 (8)	0.0240 (7)	−0.0031 (6)	−0.0067 (6)	−0.0017 (6)
O41A	0.0402 (7)	0.0236 (6)	0.0290 (6)	−0.0127 (5)	−0.0123 (5)	−0.0008 (5)
C5A	0.0247 (8)	0.0232 (8)	0.0222 (7)	−0.0030 (7)	−0.0073 (6)	−0.0021 (6)
C51A	0.0418 (10)	0.0278 (9)	0.0239 (8)	−0.0069 (8)	−0.0108 (7)	−0.0016 (6)
C6A	0.0249 (8)	0.0225 (8)	0.0215 (7)	−0.0030 (7)	−0.0073 (6)	−0.0004 (6)
C61A	0.0421 (10)	0.0262 (9)	0.0238 (8)	−0.0123 (8)	−0.0111 (7)	0.0037 (6)
N1B	0.0346 (8)	0.0222 (7)	0.0213 (6)	−0.0080 (6)	−0.0057 (6)	−0.0024 (5)
C2B	0.0249 (8)	0.0225 (8)	0.0263 (8)	−0.0046 (7)	−0.0047 (6)	−0.0020 (6)
S21B	0.0497 (3)	0.0300 (2)	0.0243 (2)	−0.0125 (2)	−0.01057 (18)	0.00578 (17)
N3B	0.0311 (8)	0.0184 (7)	0.0241 (7)	−0.0084 (6)	−0.0071 (5)	0.0010 (5)
C4B	0.0229 (8)	0.0227 (8)	0.0243 (7)	−0.0028 (6)	−0.0051 (6)	−0.0006 (6)
O41B	0.0410 (7)	0.0304 (6)	0.0260 (6)	−0.0142 (5)	−0.0123 (5)	−0.0001 (5)
C5B	0.0254 (8)	0.0204 (8)	0.0238 (7)	−0.0047 (6)	−0.0043 (6)	0.0011 (6)
C51B	0.0399 (10)	0.0266 (9)	0.0272 (8)	−0.0087 (8)	−0.0084 (7)	0.0050 (7)
C6B	0.0260 (8)	0.0209 (8)	0.0254 (8)	−0.0050 (7)	−0.0013 (6)	−0.0014 (6)
C61B	0.0425 (11)	0.0225 (8)	0.0299 (8)	−0.0113 (8)	−0.0044 (7)	−0.0026 (7)
C1X	0.057 (6)	0.033 (4)	0.043 (4)	−0.018 (4)	−0.014 (3)	0.002 (3)
C2X	0.031 (2)	0.029 (2)	0.029 (2)	−0.0054 (19)	−0.0120 (18)	−0.0015 (15)
O21X	0.062 (6)	0.036 (3)	0.025 (3)	−0.017 (4)	−0.024 (2)	−0.001 (2)
N3X	0.0390 (17)	0.0275 (15)	0.0227 (13)	−0.0097 (13)	−0.0114 (11)	−0.0013 (11)
C31X	0.048 (2)	0.034 (2)	0.0305 (18)	−0.0185 (19)	−0.0080 (16)	0.0030 (15)
C32X	0.048 (2)	0.038 (2)	0.0278 (17)	−0.0112 (18)	−0.0189 (16)	−0.0045 (14)
C1Y	0.073 (9)	0.028 (4)	0.031 (4)	−0.007 (4)	−0.024 (5)	0.012 (2)
C2Y	0.041 (2)	0.0238 (19)	0.0244 (18)	−0.010 (2)	−0.0148 (18)	−0.0017 (13)
O21Y	0.036 (3)	0.032 (2)	0.025 (4)	−0.010 (2)	−0.012 (3)	−0.004 (3)
N3Y	0.0383 (17)	0.0273 (15)	0.0233 (13)	−0.0106 (13)	−0.0115 (12)	0.0033 (11)
C31Y	0.049 (3)	0.0268 (18)	0.0370 (19)	−0.0110 (18)	−0.0230 (18)	0.0068 (15)
C32Y	0.040 (3)	0.040 (2)	0.0343 (19)	−0.009 (2)	−0.0043 (16)	−0.0038 (16)

Geometric parameters (Å, º)

N1A—C2A	1.348 (2)	C51B—H52D	0.9800
N1A—C6A	1.379 (2)	C51B—H52E	0.9800
N1A—H1A	0.880 (15)	C51B—H52F	0.9800
C2A—N3A	1.354 (2)	C6B—C61B	1.496 (2)
C2A—S21A	1.6739 (16)	C61B—H61D	0.9800
N3A—C4A	1.392 (2)	C61B—H61E	0.9800
N3A—H3A	0.878 (15)	C61B—H61F	0.9800
C4A—O41A	1.231 (2)	C1X—C2X	1.502 (12)
C4A—C5A	1.438 (2)	C1X—H1X1	0.9800
C5A—C6A	1.354 (2)	C1X—H1X2	0.9800
C5A—C51A	1.504 (2)	C1X—H1X3	0.9800
C51A—H51A	0.9800	C2X—O21X	1.251 (10)
C51A—H51B	0.9800	C2X—N3X	1.334 (5)
C51A—H51C	0.9800	N3X—C32X	1.456 (4)
C51A—H51D	0.9800	N3X—C31X	1.463 (4)
C51A—H51E	0.9800	C31X—H31A	0.9800
C51A—H51F	0.9800	C31X—H31B	0.9800
C6A—C61A	1.490 (2)	C31X—H31C	0.9800
C61A—H61A	0.9800	C32X—H32A	0.9800
C61A—H61B	0.9800	C32X—H32B	0.9800
C61A—H61C	0.9800	C32X—H32C	0.9800
N1B—C2B	1.346 (2)	C1Y—C2Y	1.492 (10)
N1B—C6B	1.377 (2)	C1Y—H1Y1	0.9800
N1B—H1B	0.858 (15)	C1Y—H1Y2	0.9800
C2B—N3B	1.363 (2)	C1Y—H1Y3	0.9800
C2B—S21B	1.6627 (16)	C2Y—O21Y	1.245 (11)
N3B—C4B	1.380 (2)	C2Y—N3Y	1.333 (5)
N3B—H3B	0.853 (15)	N3Y—C31Y	1.455 (4)
C4B—O41B	1.236 (2)	N3Y—C32Y	1.472 (5)
C4B—C5B	1.434 (2)	C31Y—H31D	0.9800
C5B—C6B	1.355 (2)	C31Y—H31E	0.9800
C5B—C51B	1.498 (2)	C31Y—H31F	0.9800
C51B—H52A	0.9800	C32Y—H32D	0.9800
C51B—H52B	0.9800	C32Y—H32E	0.9800
C51B—H52C	0.9800	C32Y—H32F	0.9800
C2A—N1A—C6A	124.04 (14)	C5B—C51B—H52A	109.5
C2A—N1A—H1A	118.9 (13)	C5B—C51B—H52B	109.5
C6A—N1A—H1A	117.0 (13)	C5B—C51B—H52C	109.5
N1A—C2A—N3A	114.98 (14)	C5B—C51B—H52D	109.5
N1A—C2A—S21A	122.83 (12)	C5B—C51B—H52E	109.5
N3A—C2A—S21A	122.19 (12)	H52D—C51B—H52E	109.5
C2A—N3A—C4A	125.95 (13)	C5B—C51B—H52F	109.5
C2A—N3A—H3A	117.2 (12)	H52D—C51B—H52F	109.5
C4A—N3A—H3A	116.7 (13)	H52E—C51B—H52F	109.5
O41A—C4A—N3A	118.97 (14)	C5B—C6B—N1B	120.36 (15)
O41A—C4A—C5A	125.06 (14)	C5B—C6B—C61B	124.03 (15)
N3A—C4A—C5A	115.97 (14)	N1B—C6B—C61B	115.59 (14)
C6A—C5A—C4A	118.42 (14)	C6B—C61B—H61D	109.5
C6A—C5A—C51A	122.97 (14)	C6B—C61B—H61E	109.5
C4A—C5A—C51A	118.61 (14)	H61D—C61B—H61E	109.5
C5A—C51A—H51A	109.5	C6B—C61B—H61F	109.5
C5A—C51A—H51B	109.5	H61D—C61B—H61F	109.5
C5A—C51A—H51C	109.5	H61E—C61B—H61F	109.5
C5A—C51A—H51D	109.5	O21X—C2X—N3X	121.2 (10)
C5A—C51A—H51E	109.5	O21X—C2X—C1X	120.8 (12)
H51D—C51A—H51E	109.5	N3X—C2X—C1X	117.9 (8)
C5A—C51A—H51F	109.5	C2X—N3X—C32X	122.2 (3)
H51D—C51A—H51F	109.5	C2X—N3X—C31X	119.9 (3)
H51E—C51A—H51F	109.5	C32X—N3X—C31X	117.6 (3)
C5A—C6A—N1A	120.65 (14)	C2Y—C1Y—H1Y1	109.5
C5A—C6A—C61A	124.69 (14)	C2Y—C1Y—H1Y2	109.5
N1A—C6A—C61A	114.66 (14)	H1Y1—C1Y—H1Y2	109.5
C6A—C61A—H61A	109.5	C2Y—C1Y—H1Y3	109.5
C6A—C61A—H61B	109.5	H1Y1—C1Y—H1Y3	109.5
H61A—C61A—H61B	109.5	H1Y2—C1Y—H1Y3	109.5
C6A—C61A—H61C	109.5	O21Y—C2Y—N3Y	122.9 (8)
H61A—C61A—H61C	109.5	O21Y—C2Y—C1Y	118.4 (10)
H61B—C61A—H61C	109.5	N3Y—C2Y—C1Y	118.6 (8)
C2B—N1B—C6B	124.58 (14)	C2Y—N3Y—C31Y	120.5 (3)
C2B—N1B—H1B	121.2 (14)	C2Y—N3Y—C32Y	122.6 (3)
C6B—N1B—H1B	114.3 (14)	C31Y—N3Y—C32Y	116.3 (3)
N1B—C2B—N3B	114.32 (14)	N3Y—C31Y—H31D	109.5
N1B—C2B—S21B	123.59 (12)	N3Y—C31Y—H31E	109.5
N3B—C2B—S21B	122.09 (12)	H31D—C31Y—H31E	109.5
C2B—N3B—C4B	126.00 (14)	N3Y—C31Y—H31F	109.5
C2B—N3B—H3B	116.6 (13)	H31D—C31Y—H31F	109.5
C4B—N3B—H3B	117.4 (13)	H31E—C31Y—H31F	109.5
O41B—C4B—N3B	119.39 (15)	N3Y—C32Y—H32D	109.5
O41B—C4B—C5B	124.13 (14)	N3Y—C32Y—H32E	109.5
N3B—C4B—C5B	116.48 (14)	H32D—C32Y—H32E	109.5
C6B—C5B—C4B	118.26 (14)	N3Y—C32Y—H32F	109.5
C6B—C5B—C51B	124.81 (15)	H32D—C32Y—H32F	109.5
C4B—C5B—C51B	116.93 (14)	H32E—C32Y—H32F	109.5
C6A—N1A—C2A—N3A	−0.4 (2)	C2B—N3B—C4B—O41B	−179.08 (16)
C6A—N1A—C2A—S21A	−179.44 (13)	C2B—N3B—C4B—C5B	0.7 (2)
N1A—C2A—N3A—C4A	1.0 (2)	O41B—C4B—C5B—C6B	179.12 (16)
S21A—C2A—N3A—C4A	−179.88 (13)	N3B—C4B—C5B—C6B	−0.6 (2)
C2A—N3A—C4A—O41A	179.32 (16)	O41B—C4B—C5B—C51B	−1.2 (3)
C2A—N3A—C4A—C5A	−0.9 (2)	N3B—C4B—C5B—C51B	179.08 (15)
O41A—C4A—C5A—C6A	179.86 (17)	C4B—C5B—C6B—N1B	0.1 (2)
N3A—C4A—C5A—C6A	0.1 (2)	C51B—C5B—C6B—N1B	−179.60 (16)
O41A—C4A—C5A—C51A	0.1 (3)	C4B—C5B—C6B—C61B	178.49 (16)
N3A—C4A—C5A—C51A	−179.63 (15)	C51B—C5B—C6B—C61B	−1.2 (3)
C4A—C5A—C6A—N1A	0.4 (2)	C2B—N1B—C6B—C5B	0.5 (3)
C51A—C5A—C6A—N1A	−179.79 (16)	C2B—N1B—C6B—C61B	−178.02 (16)
C4A—C5A—C6A—C61A	−179.66 (16)	O21X—C2X—N3X—C32X	177.4 (9)
C51A—C5A—C6A—C61A	0.1 (3)	C1X—C2X—N3X—C32X	−6.7 (10)
C2A—N1A—C6A—C5A	−0.4 (3)	O21X—C2X—N3X—C31X	3.9 (11)
C2A—N1A—C6A—C61A	179.74 (16)	C1X—C2X—N3X—C31X	179.7 (9)
C6B—N1B—C2B—N3B	−0.5 (2)	O21Y—C2Y—N3Y—C31Y	−3.5 (10)
C6B—N1B—C2B—S21B	178.75 (13)	C1Y—C2Y—N3Y—C31Y	176.3 (8)
N1B—C2B—N3B—C4B	−0.1 (2)	O21Y—C2Y—N3Y—C32Y	−174.3 (9)
S21B—C2B—N3B—C4B	−179.38 (13)	C1Y—C2Y—N3Y—C32Y	5.5 (9)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O41B	0.88 (2)	1.83 (2)	2.7111 (19)	175 (2)
N3A—H3A···O41A^i	0.88 (2)	1.96 (2)	2.8327 (18)	175 (2)
N1B—H1B···O21X	0.86 (2)	1.85 (2)	2.687 (15)	165 (2)
N1B—H1B···O21Y	0.86 (2)	2.06 (2)	2.910 (14)	171 (2)
N3B—H3B···S21A	0.85 (2)	2.56 (2)	3.4058 (15)	170 (2)

Symmetry code: (i) −x+1, −y+2, −z+1.

(IIId) 5,6-Dimethyl-2-thiouracil–dimethyl sulfoxide (2/1)

Crystal data

2C6H8N2OS·C2H6OS	F(000) = 824
Mr = 390.54	Dx = 1.382 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 13070 reflections
a = 8.1597 (14) Å	θ = 3.4–26.0°
b = 22.612 (3) Å	µ = 0.42 mm^−1
c = 10.5576 (17) Å	T = 173 K
β = 105.459 (13)°	Needle, colourless
V = 1877.5 (5) Å^3	0.55 × 0.15 × 0.10 mm
Z = 4

Data collection

Stoe IPDS II two-circle diffractometer	3518 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	2772 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	Rint = 0.116
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→9
Tmin = 0.804, Tmax = 0.960	k = −27→23
13972 measured reflections	l = −12→12

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.071	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.180	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0806P)^2 + 2.8969P] where P = (Fo^2 + 2Fc^2)/3
3518 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.43 e Å^−3
4 restraints	Δρmin = −0.34 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1A	0.8739 (4)	0.54261 (15)	0.3399 (3)	0.0198 (7)
H1A	0.830 (5)	0.538 (2)	0.406 (3)	0.024*
C2A	0.8742 (5)	0.49842 (17)	0.2538 (4)	0.0189 (8)
S21A	0.80280 (14)	0.43048 (5)	0.26911 (10)	0.0257 (3)
N3A	0.9328 (4)	0.51424 (15)	0.1504 (3)	0.0205 (7)
H3A	0.933 (6)	0.4853 (16)	0.096 (4)	0.025*
C4A	0.9912 (5)	0.56902 (18)	0.1275 (4)	0.0202 (8)
O41A	1.0435 (4)	0.57678 (13)	0.0288 (3)	0.0258 (7)
C5A	0.9825 (5)	0.61480 (18)	0.2206 (4)	0.0218 (8)
C51A	1.0367 (6)	0.6758 (2)	0.1970 (5)	0.0333 (10)
H51A	0.9376	0.6985	0.1483	0.050*
H51B	1.1206	0.6739	0.1459	0.050*
H51C	1.0874	0.6951	0.2815	0.050*
C6A	0.9263 (5)	0.59914 (18)	0.3258 (4)	0.0202 (8)
C61A	0.9149 (5)	0.64135 (17)	0.4327 (4)	0.0237 (8)
H61A	1.0253	0.6606	0.4679	0.036*
H61B	0.8838	0.6196	0.5032	0.036*
H61C	0.8283	0.6714	0.3970	0.036*
N1B	0.5470 (4)	0.38357 (16)	0.6755 (3)	0.0233 (7)
H1B	0.512 (6)	0.3497 (13)	0.701 (4)	0.028*
C2B	0.5876 (5)	0.38152 (18)	0.5598 (4)	0.0219 (8)
S21B	0.56248 (16)	0.32153 (5)	0.46540 (11)	0.0324 (3)
N3B	0.6542 (4)	0.43197 (15)	0.5266 (3)	0.0208 (7)
H3B	0.684 (6)	0.429 (2)	0.453 (3)	0.025*
C4B	0.6807 (5)	0.48410 (18)	0.5977 (4)	0.0203 (8)
O41B	0.7455 (4)	0.52696 (13)	0.5560 (3)	0.0250 (6)
C5B	0.6310 (5)	0.48390 (18)	0.7182 (4)	0.0197 (8)
C51B	0.6579 (6)	0.5401 (2)	0.7975 (4)	0.0271 (9)
H51D	0.6358	0.5327	0.8829	0.041*
H51E	0.5799	0.5706	0.7503	0.041*
H51F	0.7755	0.5535	0.8108	0.041*
C6B	0.5666 (5)	0.43343 (19)	0.7538 (4)	0.0222 (8)
C61B	0.5183 (5)	0.4258 (2)	0.8799 (4)	0.0269 (9)
H61D	0.6214	0.4225	0.9528	0.040*
H61E	0.4499	0.3898	0.8753	0.040*
H61F	0.4520	0.4601	0.8942	0.040*
C1X	0.2783 (6)	0.2095 (2)	0.6029 (5)	0.0390 (11)
H1X1	0.1612	0.2178	0.6051	0.058*
H1X2	0.2868	0.1684	0.5758	0.058*
H1X3	0.3101	0.2362	0.5402	0.058*
S2X	0.41773 (16)	0.22062 (5)	0.76211 (11)	0.0333 (3)
O21X	0.4316 (5)	0.28685 (15)	0.7835 (3)	0.0383 (8)
C3X	0.6074 (7)	0.1976 (3)	0.7238 (6)	0.0467 (13)
H3X1	0.6294	0.2234	0.6556	0.070*
H3X2	0.5943	0.1567	0.6919	0.070*
H3X3	0.7029	0.2000	0.8029	0.070*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0247 (17)	0.0162 (17)	0.0197 (16)	−0.0007 (13)	0.0082 (13)	−0.0005 (13)
C2A	0.0184 (18)	0.018 (2)	0.0209 (18)	0.0031 (15)	0.0066 (14)	0.0007 (15)
S21A	0.0360 (6)	0.0183 (5)	0.0280 (5)	−0.0038 (4)	0.0178 (4)	−0.0031 (4)
N3A	0.0256 (17)	0.0172 (17)	0.0207 (16)	−0.0001 (14)	0.0096 (13)	−0.0014 (13)
C4A	0.0186 (18)	0.022 (2)	0.0186 (18)	−0.0007 (15)	0.0017 (14)	0.0017 (15)
O41A	0.0343 (16)	0.0247 (16)	0.0223 (14)	−0.0042 (12)	0.0144 (12)	0.0006 (11)
C5A	0.0209 (19)	0.020 (2)	0.0238 (19)	0.0009 (15)	0.0042 (15)	−0.0016 (15)
C51A	0.045 (3)	0.027 (2)	0.031 (2)	−0.009 (2)	0.015 (2)	−0.0018 (18)
C6A	0.0188 (18)	0.020 (2)	0.0205 (18)	0.0038 (15)	0.0025 (14)	−0.0031 (15)
C61A	0.035 (2)	0.0147 (19)	0.0220 (19)	0.0031 (17)	0.0087 (16)	−0.0029 (15)
N1B	0.0257 (17)	0.0225 (19)	0.0226 (16)	−0.0011 (14)	0.0083 (13)	0.0010 (13)
C2B	0.0211 (19)	0.023 (2)	0.0213 (19)	0.0004 (16)	0.0048 (15)	−0.0007 (15)
S21B	0.0484 (7)	0.0225 (6)	0.0300 (6)	−0.0063 (5)	0.0167 (5)	−0.0065 (4)
N3B	0.0248 (17)	0.0200 (18)	0.0198 (15)	−0.0019 (13)	0.0099 (13)	−0.0010 (13)
C4B	0.0168 (18)	0.022 (2)	0.0216 (18)	0.0019 (15)	0.0044 (14)	0.0018 (16)
O41B	0.0303 (15)	0.0216 (15)	0.0266 (14)	−0.0021 (12)	0.0137 (12)	−0.0005 (11)
C5B	0.0159 (17)	0.021 (2)	0.0204 (18)	0.0024 (15)	0.0020 (14)	−0.0003 (15)
C51B	0.028 (2)	0.030 (2)	0.024 (2)	−0.0005 (18)	0.0090 (16)	−0.0053 (17)
C6B	0.0193 (18)	0.029 (2)	0.0175 (18)	0.0025 (16)	0.0026 (15)	−0.0005 (16)
C61B	0.030 (2)	0.030 (2)	0.024 (2)	−0.0030 (18)	0.0115 (17)	−0.0022 (17)
C1X	0.044 (3)	0.027 (3)	0.041 (3)	0.002 (2)	0.002 (2)	0.003 (2)
S2X	0.0462 (7)	0.0229 (6)	0.0312 (6)	−0.0036 (5)	0.0111 (5)	0.0071 (4)
O21X	0.060 (2)	0.0245 (17)	0.0340 (17)	−0.0076 (15)	0.0193 (15)	0.0002 (13)
C3X	0.044 (3)	0.033 (3)	0.061 (3)	0.003 (2)	0.010 (2)	0.013 (2)

Geometric parameters (Å, º)

N1A—C2A	1.351 (5)	N3B—C4B	1.383 (5)
N1A—C6A	1.368 (5)	N3B—H3B	0.877 (19)
N1A—H1A	0.873 (19)	C4B—O41B	1.240 (5)
C2A—N3A	1.352 (5)	C4B—C5B	1.434 (5)
C2A—S21A	1.666 (4)	C5B—C6B	1.351 (6)
N3A—C4A	1.372 (5)	C5B—C51B	1.505 (6)
N3A—H3A	0.875 (19)	C51B—H51D	0.9800
C4A—O41A	1.239 (5)	C51B—H51E	0.9800
C4A—C5A	1.442 (6)	C51B—H51F	0.9800
C5A—C6A	1.357 (6)	C6B—C61B	1.495 (5)
C5A—C51A	1.490 (6)	C61B—H61D	0.9800
C51A—H51A	0.9800	C61B—H61E	0.9800
C51A—H51B	0.9800	C61B—H61F	0.9800
C51A—H51C	0.9800	C1X—S2X	1.778 (5)
C6A—C61A	1.500 (5)	C1X—H1X1	0.9800
C61A—H61A	0.9800	C1X—H1X2	0.9800
C61A—H61B	0.9800	C1X—H1X3	0.9800
C61A—H61C	0.9800	S2X—O21X	1.514 (3)
N1B—C2B	1.349 (5)	S2X—C3X	1.778 (6)
N1B—C6B	1.382 (5)	C3X—H3X1	0.9800
N1B—H1B	0.882 (19)	C3X—H3X2	0.9800
C2B—N3B	1.350 (5)	C3X—H3X3	0.9800
C2B—S21B	1.663 (4)
C2A—N1A—C6A	124.2 (3)	C4B—N3B—H3B	120 (3)
C2A—N1A—H1A	122 (3)	O41B—C4B—N3B	119.6 (3)
C6A—N1A—H1A	113 (3)	O41B—C4B—C5B	124.4 (4)
N1A—C2A—N3A	114.3 (3)	N3B—C4B—C5B	116.0 (3)
N1A—C2A—S21A	123.6 (3)	C6B—C5B—C4B	118.2 (4)
N3A—C2A—S21A	122.1 (3)	C6B—C5B—C51B	124.6 (4)
C2A—N3A—C4A	126.6 (3)	C4B—C5B—C51B	117.2 (4)
C2A—N3A—H3A	114 (3)	C5B—C51B—H51D	109.5
C4A—N3A—H3A	120 (3)	C5B—C51B—H51E	109.5
O41A—C4A—N3A	119.3 (4)	H51D—C51B—H51E	109.5
O41A—C4A—C5A	124.2 (4)	C5B—C51B—H51F	109.5
N3A—C4A—C5A	116.4 (3)	H51D—C51B—H51F	109.5
C6A—C5A—C4A	117.4 (4)	H51E—C51B—H51F	109.5
C6A—C5A—C51A	123.9 (4)	C5B—C6B—N1B	120.9 (4)
C4A—C5A—C51A	118.7 (4)	C5B—C6B—C61B	124.0 (4)
C5A—C51A—H51A	109.5	N1B—C6B—C61B	115.0 (4)
C5A—C51A—H51B	109.5	C6B—C61B—H61D	109.5
H51A—C51A—H51B	109.5	C6B—C61B—H61E	109.5
C5A—C51A—H51C	109.5	H61D—C61B—H61E	109.5
H51A—C51A—H51C	109.5	C6B—C61B—H61F	109.5
H51B—C51A—H51C	109.5	H61D—C61B—H61F	109.5
C5A—C6A—N1A	121.1 (4)	H61E—C61B—H61F	109.5
C5A—C6A—C61A	123.5 (4)	S2X—C1X—H1X1	109.5
N1A—C6A—C61A	115.4 (3)	S2X—C1X—H1X2	109.5
C6A—C61A—H61A	109.5	H1X1—C1X—H1X2	109.5
C6A—C61A—H61B	109.5	S2X—C1X—H1X3	109.5
H61A—C61A—H61B	109.5	H1X1—C1X—H1X3	109.5
C6A—C61A—H61C	109.5	H1X2—C1X—H1X3	109.5
H61A—C61A—H61C	109.5	O21X—S2X—C1X	106.5 (2)
H61B—C61A—H61C	109.5	O21X—S2X—C3X	106.8 (2)
C2B—N1B—C6B	123.5 (4)	C1X—S2X—C3X	96.9 (3)
C2B—N1B—H1B	115 (3)	S2X—C3X—H3X1	109.5
C6B—N1B—H1B	121 (3)	S2X—C3X—H3X2	109.5
N1B—C2B—N3B	114.8 (4)	H3X1—C3X—H3X2	109.5
N1B—C2B—S21B	123.4 (3)	S2X—C3X—H3X3	109.5
N3B—C2B—S21B	121.8 (3)	H3X1—C3X—H3X3	109.5
C2B—N3B—C4B	126.5 (3)	H3X2—C3X—H3X3	109.5
C2B—N3B—H3B	113 (3)
C6A—N1A—C2A—N3A	0.6 (5)	C6B—N1B—C2B—N3B	1.7 (6)
C6A—N1A—C2A—S21A	−177.5 (3)	C6B—N1B—C2B—S21B	−179.5 (3)
N1A—C2A—N3A—C4A	0.7 (5)	N1B—C2B—N3B—C4B	−1.1 (6)
S21A—C2A—N3A—C4A	178.8 (3)	S21B—C2B—N3B—C4B	−179.9 (3)
C2A—N3A—C4A—O41A	179.0 (4)	C2B—N3B—C4B—O41B	179.0 (4)
C2A—N3A—C4A—C5A	−2.7 (6)	C2B—N3B—C4B—C5B	−0.3 (6)
O41A—C4A—C5A—C6A	−178.3 (4)	O41B—C4B—C5B—C6B	−178.0 (4)
N3A—C4A—C5A—C6A	3.5 (5)	N3B—C4B—C5B—C6B	1.3 (5)
O41A—C4A—C5A—C51A	1.0 (6)	O41B—C4B—C5B—C51B	0.9 (6)
N3A—C4A—C5A—C51A	−177.2 (4)	N3B—C4B—C5B—C51B	−179.8 (3)
C4A—C5A—C6A—N1A	−2.5 (5)	C4B—C5B—C6B—N1B	−0.8 (6)
C51A—C5A—C6A—N1A	178.2 (4)	C51B—C5B—C6B—N1B	−179.6 (4)
C4A—C5A—C6A—C61A	178.2 (3)	C4B—C5B—C6B—C61B	176.6 (4)
C51A—C5A—C6A—C61A	−1.1 (6)	C51B—C5B—C6B—C61B	−2.2 (6)
C2A—N1A—C6A—C5A	0.5 (6)	C2B—N1B—C6B—C5B	−0.8 (6)
C2A—N1A—C6A—C61A	179.8 (3)	C2B—N1B—C6B—C61B	−178.4 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O41B	0.87 (2)	1.90 (2)	2.776 (4)	176 (4)
N3A—H3A···O41A^i	0.88 (2)	1.96 (2)	2.837 (4)	174 (4)
N1B—H1B···O21X	0.88 (2)	1.88 (2)	2.746 (5)	168 (5)
N3B—H3B···S21A	0.88 (2)	2.39 (2)	3.258 (3)	171 (4)

Symmetry code: (i) −x+2, −y+1, −z.