Cocrystals of 6-methyl-2-thio­uracil: presence of the acceptor-donor-acceptor/donor-acceptor-donor synthon

The results of seven cocrystallization experiments of the anti­thyroid drug 6-methyl-2-thio­uracil (MTU), C₅H₆N₂OS, with 2,4-di­amino­pyrimidine, 2,4,6-tri­amino­pyrimidine and 6-amino-3H-isocytosine (viz. 2,6-diamino-3H-pyrimidin-4-one) are reported. MTU features an ADA (A = acceptor and D = donor) hydrogen-bonding site, while the three coformers show complementary DAD hydrogen-bonding sites and therefore should be capable of forming an ADA/DAD N-H...O/N-H...N/N-H...S synthon with MTU. The experiments yielded one cocrystal and six cocrystal solvates, namely 6-methyl-2-thio­uracil-2,4-di­amino­pyrimidine-1-methyl­pyrrolidin-2-one (1/1/2), C₅H₆N₂OS·C₄H₆N₄·2C₅H₉NO, (I), 6-methyl-2-thio­uracil-2,4-di­amino­pyrimidine (1/1), C₅H₆N₂OS·C₄H₆N₄, (II), 6-methyl-2-thio­uracil-2,4-di­amino­pyrimidine-N,N-di­methyl­acetamide (2/1/2), 2C₅H₆N₂OS·C₄H₆N₄·2C₄H₉NO, (III), 6-methyl-2-thio­uracil-2,4-di­amino­pyrimidine-N,N-di­methyl­formamide (2/1/2), C₅H₆N₂OS·0.5C₄H₆N₄·C₃H₇NO, (IV), 2,4,6-tri­amino­pyri­mi­din­ium 6-methyl-2-thio­uracilate-6-methyl-2-thio­uracil-N,N-di­methyl­formamide (1/1/2), C₄H₈N₅⁺·C₅H₅N₂OS^-·C₅H₆N₂OS·2C₃H₇NO, (V), 6-methyl-2-thio­uracil-6-am­ino-3H-isocytosine-N,N-di­methyl­formamide (1/1/1), C₅H₆N₂OS·C₄H₆N₄O·C₃H₇NO, (VI), and 6-methyl-2-thio­uracil-6-amino-3H-isocytosine-dimethyl sulfoxide (1/1/1), C₅H₆N₂OS·C₄H₆N₄O·C₂H₆OS, (VII). Whereas in cocrystal (I) an R₂²(8) inter­action similar to the Watson-Crick adenine/uracil base pair is formed and a two-dimensional hydrogen-bonding network is observed, the cocrystals (II)-(VII) contain the triply hydrogen-bonded ADA/DAD N-H...O/N-H...N/N-H...S synthon and show a one-dimensional hydrogen-bonding network. Although 2,4-di­amino­pyrimidine possesses only one DAD hydrogen-bonding site, it is, due to orientational disorder, triply connected to two MTU mol­ecules in (III) and (IV).

S1. Introduction

In order to design new crystalline forms of a compound with different physical properties, especially of active pharmaceutical ingredients, cocrystallization is a versatile and powerful method (Blagden et al., 2007; Shan & Zaworotko, 2008; Schultheiss & Newman, 2009). A key step within the development of the crystallization strategy is the identification of suitable coformers. Thus different tools of crystal engineering are usually applied. One of the most important design elements are hydrogen bonds, since they are highly directional and therefore obtain a good predi­cta­bility once the preferred inter­action motif of the compounds has been determined (Etter, 1991; Prins et al., 2001). For example, triply hydrogen-bonded synthons show a high stability and are often used as potential building blocks (Desiraju, 1995, 2007; Aakeröy, 1997). The combination of three hydrogen bonds gives three possible synthon types, viz. AAA/DDD, AAD/DDA or ADA/DAD (D = donor and A = acceptor). When the relative stability of these three synthons is evaluated, secondary inter­actions must be taken into account. The synthon AAA/DDD, which contains solely attractive secondary inter­actions, is therefore more stable than the AAD/DDA motif where an equal number of attractive and repulsive secondary inter­actions is observed. On the other hand, the latter is more stable than the ADA/DAD motif which shows only repulsive secondary inter­actions (Jorgensen & Pranata, 1990; Pranata et al., 1991).

The anti­thyroid drug 6-methyl-2-thio­uracil (Hershman & Van Middlesworth, 1962), in the following referred to as MTU, exhibits an ADA and an AD binding site. A search of the Cambridge Structural Database (CSD, Version 5.36 of November 2014, plus one update; Groom & Allen, 2014) revealed that no cocrystals of MTU are known. Therefore, we decided to cocrystallize MTU with 2,4-di­amino­pyrimidine (DAPY), 2,4,6-tri­amino­pyrimidine (TAPY) and 6-amino-3H-isocytosine (AICT), which show complementary DAD hydrogen-bonding sites. The experiments were supposed to validate if the ADA/DAD N—H···O/N—H···N/N—H···S synthon is formed or if other motifs are preferred instead.

S2. Experimental

S2.1. Synthesis and crystallization

Isothermal solvent evaporation experiments under different conditions with the commercially available compounds and various solvents yielded the seven cocrystal structures (I)–(VII). In Table 1, the crystallization conditions are summarized. All solvents were used as supplied without further purification.

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. 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 and 1.2U_eq(C) for secondary and aromatic H atoms. For the H atoms of the methyl groups, free rotation about their local threefold axis was allowed, except for the disordered methyl groups of molecule A in (IV) and (V), and for those of the disordered DMAC molecules in (III).

H atoms bonded to N atoms were refined isotropically with the N—H distances restrained to 0.88 (2) Å. Their isotropic displacement parameters were coupled to the U_eq parameters of the parent N atoms, with U_iso(H) = 1.2U_eq(N). In (III), H atoms bonded to minor occupied atom N41' were refined using a riding model, with N—H = 0.88 Å and U_iso(H) = 1.2U_eq(N).

In (I) and (VI), an isotropic extinction factor was refined, and in (I) one reflection was omitted.

In (IV) and (V), the H atoms of the methyl group at atom C6A show a rotational disorder [site-occupancy factors for the predominant conformation: 0.66 (3) in (IV) and 0.71 (3) in (V)].

In (II), (III) and (IV), the DAPY molecules are disordered [site-occupancy factors: 0.5 for (II) and (IV), and 0.818 (5) for the major occupied orientation in (III)]. The two DAPY molecules in (II) lie perpendicular to crystallographic mirror planes along C2B/C, N21B/C and C5B/C. In (IV), the DAPY molecule is disordered over a crystallographic twofold rotation axis along C2B, N21B and C5B. The DAPY molecule in (III) is disordered over a pseudo-mirror plane along C2C, N21C and C5C, perpendicular to the molecular plane.

In (III), the DMAC molecules are disordered over a pseudo-mirror plane along O21X/Y and C32X/Y, perpendicular to the molecular plane [site-occupancy factor for the major occupied orientation: 0.898 (4) for X and 0.615 (6) for Y]. For both DMAC molecules, similarity restraints for the 1,2- and 1,3-distances were applied, as well as similar-ADP and rigid-bond restraints (SIMU and DELU in SHELXL2014; Sheldrick, 2015).

S3. Results and discussion

6-Methyl-2-thio­uracil–2,4-di­amino­pyrimidine–1-methyl­pyrrolidin-2-one (1/1/2), (I), crystallizes in the monoclinic space group C2/c with one MTU molecule (A), one DAPY molecule (B) and two NMP molecules (X and Y) within the asymmetric unit. A and B form an R₂²(8) hydrogen-bonding pattern (Bernstein et al., 1995) consisting of one N—H···O and one N—H···N hydrogen bond, similar to the inter­actions in the Watson–Crick adenine/uracil base-pair-yielding dimers (Fig. 1). Each of the two molecules forms one additional hydrogen bond to the solvent molecules, whereby A is linked to X and B to Y. Molecules A, B and X show a coplanar arrangement (r.m.s. deviation for all non-H atoms = 0.064 Å) and enclose a dihedral angle of 64.89 (4)° with the mean plane through all non-H atoms of Y. In the crystal, further hydrogen bonds are formed, viz. a pair of crystallographically equivalent N—H···N R₂²(8) hydrogen bonds that connect B to another DAPY molecule, which enclose a dihedral angle of 70.44 (3)°, and one N—H···O hydrogen bond, establishing a connection to an additional NMP molecule Y (Fig. 2 and Table 3). As a result, a two-dimensional network parallel to (001) is formed whereby the mean planes of the MTU–DAPY dimers are orientated parallel to (112).

The asymmetric unit of cocrystal (II), namely 6-methyl-2-thio­uracil–2,4-di­amino­pyrimidine (1/1) (space group Pnma), comprises one MTU molecule (A) and two independent halves of disordered DAPY molecules (B and C). A and B are linked via R₂²(8) N—H···N and N—H···O hydrogen bonds. Due to the disorder of B, an additional N—H···S hydrogen bond is formed between atoms N41B and S21A, thus establishing the desired ADA/DAD inter­action (Fig. 3). Molecules A and C are connected by an N—H···N hydrogen bond and also, as a result of the disorder of atom N41C, form an N—H···S hydrogen bond, resulting in an R₂²(8) pattern. The molecules are tilted against each other, enclosing dihedral angles of 33.13 (12)° between molecules A and B, and 52.85 (12)° between molecules A and C with respect to the planes through all non-H atoms of each molecule. In the crystal packing, the molecules form `double' chains along the b axis stabilized by additional N—H···O hydrogen bonds [Fig. 4, Fig. S1 (in the Supporting information) and Table 4].

The cocrystal 6-methyl-2-thio­uracil–2,4-di­amino­pyrimidine–N,N-di­methyl­acetamide (2/1/2), (III), is triclinic (space group P1), with two MTU molecules (A and B) one disordered DAPY molecule (C) and two disordered DMAC molecules (X and Y) in the asymmetric unit. All molecules show an almost coplanar arrangement (Fig. 5; r.m.s. deviation for all non-H atoms = 0.126 Å). Molecules A and C form the ADA/DAD N—H···S/N—H···N/N—H···O inter­action when C adopts its major occupied orientation, while R₂²(8) N—H···N and N—H···O hydrogen bonds are formed if the minor occupied orientation of C is present. For the inter­actions between molecules B and C, the hydrogen-bonding pattern is vice versa. Each of the MTU molecules is linked to one of the DMAC molecules via one N—H···O hydrogen bond connecting A with X and B with Y. In the crystal, additional N—H···O hydrogen bonds yield chains running along the a axis, with the mean plane through all non-H atoms lying parallel to (014) (Fig. 6 and Table 5).

The fourth cocrystal between MTU and DAPY, namely 6-methyl-2-thio­uracil–2,4-di­amino­pyrimidine–N,N-di­methyl­formamide (2/1/2), (IV), crystallizes in the monoclinic space group C2/c with one MTU molecule (A), one half of a disordered DAPY molecule (B) and one DMF molecule (X) in the asymmetric unit. Molecules A, B and C show a nearly coplanar arrangement (Fig. 7; r.m.s. deviation for all non-H atoms = 0.103 Å). The hydrogen-bonding pattern is similar to that observed in (III). Molecules A and B form ADA/DAD inter­actions or an R₂²(8) hydrogen-bonding pattern, depending on the orientation of the disordered DAPY molecule. The MTU molecule is linked to the solvent molecule via one N—H···O hydrogen bond. As in (III), the crystal packing is stabilized by an additional N—H···O hydrogen bond between molecule B and a symmetry-equivalent of molecule A, leading to a similar arrangement of chains, which are parallel to (201) (Fig. 8 and Table 6).

The asymmetric unit of the structure of 2,4,6-tri­amino­pyrimidinium 6-methyl-2-thio­uracilate–6-methyl-2-thio­uracil–N,N-di­methyl­formamide (1/1/2), (V) (space group P2₁/m), contains one neutral MTU molecule (A), one 6-methyl-2-thio­uracilate ion (B), which is formed from MTU by deprotonation at atom N3B, one 2,4,6-tri­amino­pyrimidinium ion (C), formed from TAPY by protonation at atom N3C, and two DMF molecules (X and Y), whereby all five entities are located on a crystallographic mirror plane. Both A and B show a three-point N—H···S/N—H···N/N—H···O hydrogen-bonding inter­action with C, but the patterns are different. There is an ADA/DAD pattern between molecules A and C, while an AAA/DDD motif is present between molecules B and C (Fig. 9). In the crystal, two additional N—H···O hydrogen bonds are formed which establish an R₄²(12) hydrogen-bonding pattern, leading to a one-dimensional network running along the a axis (Fig. 10 and Table 7). This arrangement is similar to that observed in (IV), but in contrast the two DMF molecules adopt different orientations, i.e. in the A/X molecule pair, the H atom at C1X points towards S21A, while that at C1Y in the B/Y molecule pair points towards C61B.

6-Methyl-2-thio­uracil–6-amino-(3H)-isocytosine–N,N-di­methyl­formamide (1/1/1), (VI), is also monoclinic (space group P2₁/n), with one MTU molecule (A), one AICT molecule (B) and one DMF molecule (X) in the asymmetric unit. A and B are connected to dimers by the ADA/DAD inter­action and A and X are linked via a single N—H···O hydrogen bond (Fig. 11). In the crystal packing, three further N—H···O hydrogen bonds are formed yielding R₄³(14) and R₂¹(6) patterns which connect each the A–B heterodimer with four adjacent dimers. As a result, layer-like ribbons are formed, with the mean plane through all non-H atoms oriented parallel to (101) (Fig. 12 and Table 8).

The component molecules of the second cocrystal formed between MTU and AICT, 6-methyl-2-thio­uracil–6-amino-3H-isocytosine–di­methyl sulfoxide (1/1/1), (VII), show the same hydrogen-bonding pattern as observed in (VI), but the crystal packing is somewhat different. The space group is P2₁/c and the asymmetric unit comprises one MTU molecule (A) and one AICT molecule (B), which are connected to a dimer via the ADA/DAD inter­action, together with one solvent molecule (X), linked to A by a single N—H···O hydrogen bond (Fig. 13). As in (VI), three additional N—H···O hydrogen bonds form R₄³(14) and R₂¹(6) patterns connecting the A–B heterodimer with four adjacent dimers (Fig. 14 and Table 9). In contrast to (VI), the resulting ribbons show a vaulted shape, with a dihedral angle of 71.80 (3)° between the molecular planes of MTU molecules A and Aⁱ. As a result, in the crystal packing, a wave-like arrangement is observed (see Figs. S2 and S3 in the Supporting information), with the one-dimensional hydrogen bonding extending in the c-axis direction.

A comparison of the structures of the seven cocrystals reveals that only in (I) is the desired ADA/DAD N—H···S/N—H···N/N—H···O synthon not formed. In (III) and (IV), surprisingly, a 2:1 ratio of MTU and DAPY is found and due to an orientational disorder of DAPY a double ADA/DAD inter­action is simulated. Also, in structure (V), a 2:1 ratio of MTU and the coformer is observed, but in this case a `true' double ADA/DAD inter­action is expected since the coformer TAPY possesses two DAD binding sites. However, only one ADA/DAD inter­action is observed, while the second motif is changed into AAA/DDD due to proton transfer from MTU to TAPY. In (III) and (IV), the solvent molecules show the same orientation with respect to the S atom of the MTU molecules, while in (V) the solvent molecules show two different orientations. Another difference becomes obvious when comparing the orientation of the C═S groups in adjacent ribbons. While these groups show a parallel orientation in (IV) and (V) they are anti­parallel in (III). Structures (VI) and (VII) show identical hydrogen-bonding inter­actions and differ only in the packing of the resulting ribbons. In all structures exhibiting an ADA/DAD inter­action [i.e. (II)–(VII)], one-dimensional networks are formed; in (III)–(VI), a layer-like arrangement is found and in (VII) undulated layers are observed.

In conclusion, six of the seven cocrystal structures contain the ADA/DAD N—H···S/N—H···N/N—H···O synthon and only in one structure a heterodimer with an AD/DA inter­action is formed instead. Hence, it is shown that the ADA/DAD synthon is a feasible building block for the design of cocrystals of MTU, leading to hydrogen-bonded one-dimensional networks with either chains or a layer-like arrangement of the molecules.

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) for (I), (IV), (V), (VI), (VII); SHELXD (Sheldrick, 2008) for (II), (III). Program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015) for (I), (II), (III), (IV), (V), (VII); SHELXL3013 (Sheldrick, 2015) for (VI). For all compounds, 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 hydrogen bonds.
	Fig. 2. A partial packing diagram for (I). Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) -x+1, y, -z+1/2; (ii) x+1/2, y+1/2, z.]
	Fig. 3. A perspective view of (II), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds. Atoms without labels are displayed for the sake of clarity but are not part of the asymmetric unit. Atoms N41B and N41C are disordered and for each only one of the two equally occupied positions is shown.
	Fig. 4. A partial packing diagram for (II). Hydrogen bonds are shown as dashed lines. Only one position for each of disordered atoms N41B and N41C is shown. [Symmetry code: (i) -x+1, -y+1, -z+1].
	Fig. 5. A perspective view of (III), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds. Molecules C, X and Y are disordered and only the major occupied sites are shown.
	Fig. 6. A partial packing diagram for (III). Hydrogen bonds are shown as dashed lines. For disordered molecules C, X and Y, only the major occupied sites are displayed. [Symmetry code: (i) x-1, y, z.]
	Fig. 7. A perspective view of (IV), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds. Atoms without labels are displayed for the sake of clarity but are not part of the asymmetric unit. Atom N41B adopts two equally occupied positions of which only one is shown.
	Fig. 8. A partial packing diagram for (IV). Hydrogen bonds are shown as dashed lines. Only one position is shown for disordered atom N41B. [Symmetry code: (i) x, y+1, z.]
	Fig. 9. A perspective view of (V), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 10. A partial packing diagram for (V). Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) x+1, y, z.]
	Fig. 11. A perspective view of (VI), 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 (VI). Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) x-1/2, -y+1/2, z-1/2; (ii) x+1, y, z+1.]
	Fig. 13. A perspective view of (VII), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 14. A partial packing diagram for (VII). Hydrogen bonds are shown as dashed lines. [Symmetry codes: (i) x, -y+3/2, z-1/2; (ii) x, y, z+1.]

(I) 6-Methyl-2-thiouracil–2,4-diaminopyrimidine–1-methylpyrrolidin-2-one (1/1/2)

Crystal data

C5H6N2OS·C4H6N4·2C5H9NO	F(000) = 1920
Mr = 450.57	Dx = 1.298 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.9475 (5) Å	Cell parameters from 20467 reflections
b = 8.1618 (3) Å	θ = 2.0–26.6°
c = 40.9157 (14) Å	µ = 0.18 mm^−1
β = 98.148 (3)°	T = 173 K
V = 4610.7 (3) Å^3	Block, colourless
Z = 8	0.38 × 0.28 × 0.24 mm

Data collection

Stoe IPDS II two-circle diffractometer	3920 reflections with I > 2σ(I)
ω scans	Rint = 0.059
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	θmax = 25.9°, θmin = 2.0°
Tmin = 0.940, Tmax = 0.959	h = −17→17
17630 measured reflections	k = −10→10
4449 independent reflections	l = −50→50

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.044	w = 1/[σ^2(Fo^2) + (0.0661P)^2 + 2.2641P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max < 0.001
S = 1.04	Δρmax = 0.26 e Å^−3
4449 reflections	Δρmin = −0.22 e Å^−3
302 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
6 restraints	Extinction coefficient: 0.0153 (12)

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.

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

	x	y	z	Uiso*/Ueq
N1A	0.20053 (9)	0.38539 (16)	0.03379 (3)	0.0399 (3)
H1A	0.2103 (12)	0.424 (2)	0.0145 (4)	0.048*
C2A	0.27205 (10)	0.41254 (18)	0.05938 (3)	0.0388 (3)
S21A	0.37186 (3)	0.51727 (5)	0.05458 (2)	0.04795 (17)
N3A	0.25643 (9)	0.35139 (16)	0.08908 (3)	0.0402 (3)
H3A	0.3035 (11)	0.361 (2)	0.1066 (4)	0.048*
C4A	0.17400 (11)	0.2659 (2)	0.09475 (4)	0.0439 (4)
O41A	0.16813 (9)	0.21340 (17)	0.12273 (3)	0.0569 (3)
C5A	0.10174 (11)	0.2464 (2)	0.06674 (4)	0.0458 (4)
H5A	0.0429	0.1921	0.0691	0.055*
C6A	0.11602 (11)	0.30425 (19)	0.03690 (4)	0.0418 (3)
C61A	0.04551 (12)	0.2816 (2)	0.00623 (4)	0.0523 (4)
H61A	0.0668	0.1910	−0.0067	0.078*
H61B	0.0419	0.3824	−0.0069	0.078*
H61C	−0.0186	0.2566	0.0121	0.078*
N1B	0.39775 (9)	0.38963 (16)	0.14669 (3)	0.0429 (3)
C2B	0.39090 (11)	0.32839 (18)	0.17693 (3)	0.0405 (3)
N21B	0.31472 (11)	0.2322 (2)	0.18013 (3)	0.0533 (4)
H21B	0.2685 (13)	0.221 (3)	0.1632 (4)	0.064*
H22B	0.3088 (14)	0.195 (3)	0.1996 (4)	0.064*
N3B	0.45418 (9)	0.35313 (16)	0.20450 (3)	0.0406 (3)
C4B	0.53318 (11)	0.44281 (19)	0.20177 (4)	0.0403 (3)
N41B	0.59609 (10)	0.4652 (2)	0.22930 (3)	0.0495 (3)
H41B	0.5859 (14)	0.416 (2)	0.2477 (4)	0.059*
H42B	0.6495 (12)	0.521 (2)	0.2290 (5)	0.059*
C5B	0.54775 (12)	0.51074 (19)	0.17109 (4)	0.0444 (4)
H5B	0.6035	0.5742	0.1687	0.053*
C6B	0.47774 (12)	0.48045 (19)	0.14504 (4)	0.0446 (4)
H6B	0.4858	0.5265	0.1243	0.054*
N1X	0.20113 (12)	0.57152 (19)	−0.08256 (3)	0.0557 (4)
C11X	0.10974 (16)	0.5073 (3)	−0.09833 (5)	0.0722 (6)
H11A	0.0800	0.4414	−0.0825	0.108*
H11B	0.1206	0.4387	−0.1171	0.108*
H11C	0.0666	0.5982	−0.1061	0.108*
C2X	0.23073 (13)	0.5613 (2)	−0.05053 (4)	0.0498 (4)
O21X	0.18904 (10)	0.48554 (17)	−0.03060 (3)	0.0636 (4)
C3X	0.32337 (14)	0.6574 (2)	−0.04226 (5)	0.0616 (5)
H3X1	0.3747	0.5886	−0.0299	0.074*
H3X2	0.3130	0.7548	−0.0288	0.074*
C4X	0.35085 (17)	0.7080 (3)	−0.07539 (6)	0.0767 (6)
H4X1	0.4062	0.6422	−0.0808	0.092*
H4X2	0.3687	0.8254	−0.0753	0.092*
C5X	0.25957 (18)	0.6753 (3)	−0.10055 (5)	0.0703 (6)
H5X1	0.2254	0.7788	−0.1074	0.084*
H5X2	0.2763	0.6188	−0.1204	0.084*
N1Y	0.28744 (13)	0.1377 (2)	0.30168 (4)	0.0636 (4)
C11Y	0.20338 (19)	0.2384 (3)	0.30255 (6)	0.0819 (6)
H11D	0.2228	0.3426	0.3134	0.123*
H11E	0.1579	0.1818	0.3149	0.123*
H11F	0.1721	0.2595	0.2800	0.123*
C2Y	0.31855 (15)	0.0906 (3)	0.27389 (4)	0.0627 (5)
O21Y	0.27970 (11)	0.1220 (2)	0.24569 (3)	0.0788 (5)
C3Y	0.4097 (2)	−0.0074 (4)	0.28289 (7)	0.0910 (8)
H3Y1	0.4648	0.0461	0.2743	0.109*
H3Y2	0.4017	−0.1192	0.2735	0.109*
C4Y	0.4271 (2)	−0.0142 (3)	0.32012 (7)	0.0866 (7)
H4Y1	0.4915	0.0320	0.3287	0.104*
H4Y2	0.4244	−0.1287	0.3279	0.104*
C5Y	0.34745 (19)	0.0870 (3)	0.33169 (5)	0.0731 (6)
H5Y1	0.3098	0.0207	0.3456	0.088*
H5Y2	0.3747	0.1833	0.3445	0.088*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0421 (6)	0.0453 (7)	0.0317 (6)	−0.0052 (5)	0.0033 (5)	0.0009 (5)
C2A	0.0424 (7)	0.0413 (7)	0.0326 (7)	−0.0015 (6)	0.0050 (6)	−0.0007 (6)
S21A	0.0447 (2)	0.0607 (3)	0.0382 (2)	−0.01528 (17)	0.00502 (16)	0.00312 (16)
N3A	0.0407 (6)	0.0472 (7)	0.0324 (6)	−0.0082 (5)	0.0037 (5)	0.0005 (5)
C4A	0.0455 (8)	0.0500 (8)	0.0366 (8)	−0.0103 (6)	0.0077 (6)	−0.0017 (6)
O41A	0.0594 (7)	0.0770 (8)	0.0344 (6)	−0.0257 (6)	0.0072 (5)	0.0039 (5)
C5A	0.0421 (8)	0.0551 (9)	0.0402 (8)	−0.0120 (7)	0.0061 (6)	−0.0029 (7)
C6A	0.0410 (7)	0.0447 (8)	0.0391 (8)	−0.0045 (6)	0.0032 (6)	−0.0039 (6)
C61A	0.0483 (9)	0.0633 (10)	0.0431 (9)	−0.0106 (8)	−0.0012 (7)	−0.0018 (7)
N1B	0.0463 (7)	0.0509 (7)	0.0312 (6)	−0.0070 (6)	0.0045 (5)	0.0020 (5)
C2B	0.0441 (7)	0.0444 (8)	0.0332 (7)	−0.0026 (6)	0.0058 (6)	0.0005 (6)
N21B	0.0533 (8)	0.0706 (9)	0.0343 (7)	−0.0214 (7)	0.0010 (6)	0.0074 (6)
N3B	0.0416 (6)	0.0474 (7)	0.0324 (6)	−0.0033 (5)	0.0035 (5)	0.0010 (5)
C4B	0.0417 (7)	0.0441 (8)	0.0348 (7)	−0.0005 (6)	0.0042 (6)	0.0004 (6)
N41B	0.0441 (7)	0.0658 (9)	0.0367 (7)	−0.0097 (6)	−0.0005 (6)	0.0062 (6)
C5B	0.0450 (8)	0.0511 (9)	0.0370 (8)	−0.0081 (6)	0.0056 (6)	0.0032 (6)
C6B	0.0498 (8)	0.0505 (9)	0.0338 (7)	−0.0058 (7)	0.0065 (6)	0.0044 (6)
N1X	0.0709 (9)	0.0575 (8)	0.0378 (7)	0.0031 (7)	0.0045 (6)	0.0025 (6)
C11X	0.0699 (13)	0.0812 (14)	0.0585 (12)	0.0098 (10)	−0.0149 (10)	−0.0131 (10)
C2X	0.0597 (10)	0.0492 (9)	0.0394 (8)	0.0011 (7)	0.0026 (7)	0.0034 (7)
O21X	0.0746 (9)	0.0735 (9)	0.0404 (7)	−0.0183 (7)	0.0006 (6)	0.0106 (6)
C3X	0.0630 (11)	0.0525 (10)	0.0665 (12)	−0.0059 (8)	−0.0012 (9)	0.0012 (8)
C4X	0.0746 (13)	0.0655 (12)	0.0964 (17)	−0.0024 (10)	0.0339 (12)	0.0077 (11)
C5X	0.1026 (16)	0.0615 (11)	0.0524 (11)	0.0082 (11)	0.0300 (11)	0.0102 (9)
N1Y	0.0876 (11)	0.0638 (9)	0.0387 (8)	−0.0133 (8)	0.0066 (7)	0.0045 (7)
C11Y	0.0978 (17)	0.0765 (14)	0.0734 (14)	0.0014 (13)	0.0193 (12)	0.0106 (12)
C2Y	0.0734 (12)	0.0738 (12)	0.0404 (9)	−0.0335 (10)	0.0060 (8)	−0.0041 (8)
O21Y	0.0838 (10)	0.1152 (12)	0.0363 (7)	−0.0523 (9)	0.0042 (6)	0.0009 (7)
C3Y	0.0838 (16)	0.1028 (19)	0.0854 (17)	−0.0163 (14)	0.0084 (13)	−0.0299 (14)
C4Y	0.0903 (17)	0.0787 (15)	0.0865 (17)	−0.0133 (13)	−0.0024 (14)	0.0153 (12)
C5Y	0.1074 (17)	0.0653 (12)	0.0416 (10)	−0.0170 (12)	−0.0061 (10)	0.0046 (8)

Geometric parameters (Å, º)

N1A—C2A	1.3582 (18)	N1X—C5X	1.447 (3)
N1A—C6A	1.3736 (19)	C11X—H11A	0.9800
N1A—H1A	0.877 (14)	C11X—H11B	0.9800
C2A—N3A	1.3595 (19)	C11X—H11C	0.9800
C2A—S21A	1.6686 (15)	C2X—O21X	1.233 (2)
N3A—C4A	1.3920 (19)	C2X—C3X	1.508 (3)
N3A—H3A	0.906 (14)	C3X—C4X	1.517 (3)
C4A—O41A	1.2361 (18)	C3X—H3X1	0.9900
C4A—C5A	1.424 (2)	C3X—H3X2	0.9900
C5A—C6A	1.350 (2)	C4X—C5X	1.543 (3)
C5A—H5A	0.9500	C4X—H4X1	0.9900
C6A—C61A	1.492 (2)	C4X—H4X2	0.9900
C61A—H61A	0.9800	C5X—H5X1	0.9900
C61A—H61B	0.9800	C5X—H5X2	0.9900
C61A—H61C	0.9800	N1Y—C2Y	1.330 (2)
N1B—C6B	1.349 (2)	N1Y—C11Y	1.436 (3)
N1B—C2B	1.3506 (19)	N1Y—C5Y	1.445 (3)
C2B—N21B	1.342 (2)	C11Y—H11D	0.9800
C2B—N3B	1.3453 (19)	C11Y—H11E	0.9800
N21B—H21B	0.880 (15)	C11Y—H11F	0.9800
N21B—H22B	0.869 (15)	C2Y—O21Y	1.230 (2)
N3B—C4B	1.3406 (19)	C2Y—C3Y	1.503 (4)
C4B—N41B	1.339 (2)	C3Y—C4Y	1.509 (4)
C4B—C5B	1.413 (2)	C3Y—H3Y1	0.9900
N41B—H41B	0.882 (15)	C3Y—H3Y2	0.9900
N41B—H42B	0.874 (15)	C4Y—C5Y	1.514 (4)
C5B—C6B	1.362 (2)	C4Y—H4Y1	0.9900
C5B—H5B	0.9500	C4Y—H4Y2	0.9900
C6B—H6B	0.9500	C5Y—H5Y1	0.9900
N1X—C2X	1.320 (2)	C5Y—H5Y2	0.9900
N1X—C11X	1.443 (3)
C2A—N1A—C6A	123.60 (13)	H11B—C11X—H11C	109.5
C2A—N1A—H1A	116.5 (12)	O21X—C2X—N1X	125.32 (17)
C6A—N1A—H1A	119.9 (12)	O21X—C2X—C3X	125.58 (16)
N1A—C2A—N3A	115.84 (13)	N1X—C2X—C3X	109.10 (16)
N1A—C2A—S21A	121.79 (11)	C2X—C3X—C4X	104.95 (16)
N3A—C2A—S21A	122.36 (11)	C2X—C3X—H3X1	110.8
C2A—N3A—C4A	125.01 (13)	C4X—C3X—H3X1	110.8
C2A—N3A—H3A	119.1 (11)	C2X—C3X—H3X2	110.8
C4A—N3A—H3A	115.8 (11)	C4X—C3X—H3X2	110.8
O41A—C4A—N3A	119.53 (14)	H3X1—C3X—H3X2	108.8
O41A—C4A—C5A	125.04 (14)	C3X—C4X—C5X	105.08 (16)
N3A—C4A—C5A	115.42 (13)	C3X—C4X—H4X1	110.7
C6A—C5A—C4A	120.69 (14)	C5X—C4X—H4X1	110.7
C6A—C5A—H5A	119.7	C3X—C4X—H4X2	110.7
C4A—C5A—H5A	119.7	C5X—C4X—H4X2	110.7
C5A—C6A—N1A	119.41 (13)	H4X1—C4X—H4X2	108.8
C5A—C6A—C61A	123.59 (14)	N1X—C5X—C4X	103.45 (16)
N1A—C6A—C61A	116.98 (13)	N1X—C5X—H5X1	111.1
C6A—C61A—H61A	109.5	C4X—C5X—H5X1	111.1
C6A—C61A—H61B	109.5	N1X—C5X—H5X2	111.1
H61A—C61A—H61B	109.5	C4X—C5X—H5X2	111.1
C6A—C61A—H61C	109.5	H5X1—C5X—H5X2	109.0
H61A—C61A—H61C	109.5	C2Y—N1Y—C11Y	123.57 (18)
H61B—C61A—H61C	109.5	C2Y—N1Y—C5Y	115.09 (19)
C6B—N1B—C2B	114.55 (13)	C11Y—N1Y—C5Y	121.28 (18)
N21B—C2B—N3B	116.12 (13)	N1Y—C11Y—H11D	109.5
N21B—C2B—N1B	117.75 (13)	N1Y—C11Y—H11E	109.5
N3B—C2B—N1B	126.12 (13)	H11D—C11Y—H11E	109.5
C2B—N21B—H21B	119.0 (14)	N1Y—C11Y—H11F	109.5
C2B—N21B—H22B	118.3 (14)	H11D—C11Y—H11F	109.5
H21B—N21B—H22B	122.1 (19)	H11E—C11Y—H11F	109.5
C4B—N3B—C2B	117.48 (12)	O21Y—C2Y—N1Y	126.0 (2)
N41B—C4B—N3B	116.92 (13)	O21Y—C2Y—C3Y	125.8 (2)
N41B—C4B—C5B	122.31 (14)	N1Y—C2Y—C3Y	108.14 (19)
N3B—C4B—C5B	120.77 (13)	C2Y—C3Y—C4Y	106.1 (2)
C4B—N41B—H41B	119.3 (13)	C2Y—C3Y—H3Y1	110.5
C4B—N41B—H42B	121.2 (14)	C4Y—C3Y—H3Y1	110.5
H41B—N41B—H42B	119.3 (19)	C2Y—C3Y—H3Y2	110.5
C6B—C5B—C4B	116.52 (14)	C4Y—C3Y—H3Y2	110.5
C6B—C5B—H5B	121.7	H3Y1—C3Y—H3Y2	108.7
C4B—C5B—H5B	121.7	C3Y—C4Y—C5Y	106.0 (2)
N1B—C6B—C5B	124.53 (14)	C3Y—C4Y—H4Y1	110.5
N1B—C6B—H6B	117.7	C5Y—C4Y—H4Y1	110.5
C5B—C6B—H6B	117.7	C3Y—C4Y—H4Y2	110.5
C2X—N1X—C11X	123.59 (17)	C5Y—C4Y—H4Y2	110.5
C2X—N1X—C5X	115.02 (16)	H4Y1—C4Y—H4Y2	108.7
C11X—N1X—C5X	120.70 (17)	N1Y—C5Y—C4Y	104.64 (18)
N1X—C11X—H11A	109.5	N1Y—C5Y—H5Y1	110.8
N1X—C11X—H11B	109.5	C4Y—C5Y—H5Y1	110.8
H11A—C11X—H11B	109.5	N1Y—C5Y—H5Y2	110.8
N1X—C11X—H11C	109.5	C4Y—C5Y—H5Y2	110.8
H11A—C11X—H11C	109.5	H5Y1—C5Y—H5Y2	108.9
C6A—N1A—C2A—N3A	1.1 (2)	C4B—C5B—C6B—N1B	−0.9 (2)
C6A—N1A—C2A—S21A	−177.92 (12)	C11X—N1X—C2X—O21X	6.2 (3)
N1A—C2A—N3A—C4A	−0.3 (2)	C5X—N1X—C2X—O21X	176.65 (18)
S21A—C2A—N3A—C4A	178.71 (12)	C11X—N1X—C2X—C3X	−173.63 (17)
C2A—N3A—C4A—O41A	178.83 (15)	C5X—N1X—C2X—C3X	−3.2 (2)
C2A—N3A—C4A—C5A	−1.1 (2)	O21X—C2X—C3X—C4X	173.00 (19)
O41A—C4A—C5A—C6A	−178.08 (17)	N1X—C2X—C3X—C4X	−7.2 (2)
N3A—C4A—C5A—C6A	1.9 (2)	C2X—C3X—C4X—C5X	13.7 (2)
C4A—C5A—C6A—N1A	−1.2 (2)	C2X—N1X—C5X—C4X	11.9 (2)
C4A—C5A—C6A—C61A	177.14 (15)	C11X—N1X—C5X—C4X	−177.36 (17)
C2A—N1A—C6A—C5A	−0.4 (2)	C3X—C4X—C5X—N1X	−15.2 (2)
C2A—N1A—C6A—C61A	−178.81 (14)	C11Y—N1Y—C2Y—O21Y	−1.9 (3)
C6B—N1B—C2B—N21B	−177.82 (15)	C5Y—N1Y—C2Y—O21Y	−178.88 (18)
C6B—N1B—C2B—N3B	1.5 (2)	C11Y—N1Y—C2Y—C3Y	177.9 (2)
N21B—C2B—N3B—C4B	177.17 (14)	C5Y—N1Y—C2Y—C3Y	1.0 (2)
N1B—C2B—N3B—C4B	−2.1 (2)	O21Y—C2Y—C3Y—C4Y	−179.16 (19)
C2B—N3B—C4B—N41B	−179.33 (14)	N1Y—C2Y—C3Y—C4Y	1.0 (3)
C2B—N3B—C4B—C5B	1.2 (2)	C2Y—C3Y—C4Y—C5Y	−2.4 (3)
N41B—C4B—C5B—C6B	−179.26 (16)	C2Y—N1Y—C5Y—C4Y	−2.5 (2)
N3B—C4B—C5B—C6B	0.2 (2)	C11Y—N1Y—C5Y—C4Y	−179.54 (19)
C2B—N1B—C6B—C5B	0.1 (2)	C3Y—C4Y—C5Y—N1Y	2.9 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21X	0.88 (1)	1.90 (2)	2.7413 (17)	162 (2)
N3A—H3A···N1B	0.91 (1)	1.96 (1)	2.8674 (18)	175 (2)
N21B—H21B···O41A	0.88 (2)	2.01 (2)	2.8914 (18)	175 (2)
N21B—H22B···O21Y	0.87 (2)	2.07 (2)	2.9351 (19)	173 (2)
N41B—H41B···N3B^i	0.88 (2)	2.17 (2)	3.0334 (19)	166 (2)
N41B—H42B···O21Y^ii	0.87 (2)	2.02 (2)	2.8565 (19)	159 (2)

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

(II) 6-Methyl-2-thiouracil–2,4-diaminopyrimidine (1/1)

Crystal data

C5H6N2OS·C4H6N4	Dx = 1.453 Mg m^−3
Mr = 252.31	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pnma	Cell parameters from 4338 reflections
a = 6.9996 (8) Å	θ = 3.3–25.9°
b = 19.223 (2) Å	µ = 0.28 mm^−1
c = 17.143 (2) Å	T = 173 K
V = 2306.6 (4) Å^3	Plate, colourless
Z = 8	0.14 × 0.10 × 0.09 mm
F(000) = 1056

Data collection

Stoe IPDS II two-circle diffractometer	1279 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.103
ω scans	θmax = 25.7°, θmin = 3.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −8→7
Tmin = 0.965, Tmax = 0.977	k = −23→23
11786 measured reflections	l = −17→20
2234 independent reflections

Refinement

Refinement on F^2	8 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.111	w = 1/[σ^2(Fo^2) + (0.0416P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.93	(Δ/σ)max < 0.001
2234 reflections	Δρmax = 0.26 e Å^−3
197 parameters	Δρmin = −0.23 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.2237 (4)	0.44072 (12)	0.55117 (17)	0.0328 (7)
H1A	0.218 (5)	0.4007 (11)	0.5768 (17)	0.039*
C2A	0.2346 (4)	0.49946 (16)	0.59457 (17)	0.0310 (6)
S21A	0.21417 (15)	0.49976 (5)	0.69140 (5)	0.0503 (3)
N3A	0.2653 (4)	0.55891 (12)	0.55375 (16)	0.0279 (6)
H3A	0.283 (4)	0.5981 (11)	0.5821 (16)	0.033*
C4A	0.2883 (5)	0.56398 (14)	0.4742 (2)	0.0314 (7)
O41A	0.3216 (3)	0.62137 (10)	0.44443 (12)	0.0399 (6)
C5A	0.2679 (5)	0.49955 (17)	0.43221 (17)	0.0327 (7)
H5A	0.2757	0.4992	0.3769	0.039*
C6A	0.2378 (4)	0.43998 (15)	0.4713 (2)	0.0301 (8)
C61A	0.2194 (5)	0.37000 (15)	0.4343 (2)	0.0403 (9)
H61A	0.2278	0.3747	0.3775	0.061*
H61B	0.0957	0.3496	0.4483	0.061*
H61C	0.3225	0.3397	0.4529	0.061*
C2B	0.2918 (6)	0.7500	0.6008 (3)	0.0280 (10)
N21B	0.2073 (6)	0.7500	0.5310 (2)	0.0319 (9)
H21B	0.217 (5)	0.7139 (12)	0.5017 (16)	0.038*
N3B	0.3282 (4)	0.68777 (11)	0.63403 (15)	0.0317 (6)
C4B	0.4142 (5)	0.68906 (17)	0.7040 (2)	0.0388 (8)
H4B	0.4431	0.6461	0.7287	0.047*	0.5
N41B	0.4704 (9)	0.6345 (3)	0.7398 (4)	0.0409 (14)	0.5
H41B	0.446 (10)	0.5924 (17)	0.724 (4)	0.049*	0.5
H42B	0.534 (9)	0.635 (4)	0.783 (2)	0.049*	0.5
C5B	0.4626 (7)	0.7500	0.7420 (3)	0.0461 (13)
H5B	0.5253	0.7500	0.7911	0.055*
C2C	0.2411 (6)	0.2500	0.6172 (3)	0.0271 (10)
N21C	0.4098 (6)	0.2500	0.5813 (3)	0.0402 (11)
H21C	0.474 (5)	0.2879 (12)	0.590 (2)	0.048*
N3C	0.1610 (4)	0.31182 (11)	0.63317 (17)	0.0370 (7)
C4C	−0.0051 (5)	0.31044 (17)	0.6716 (2)	0.0449 (9)
H4C	−0.0613	0.3535	0.6864	0.054*	0.5
N41C	−0.0641 (8)	0.3658 (3)	0.7131 (4)	0.0402 (15)	0.5
H41C	0.014 (8)	0.402 (2)	0.713 (4)	0.048*	0.5
H42C	−0.169 (7)	0.369 (3)	0.742 (4)	0.048*	0.5
C5C	−0.0986 (7)	0.2500	0.6909 (3)	0.0393 (11)
H5C	−0.2197	0.2500	0.7159	0.047*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0342 (17)	0.0237 (14)	0.0405 (19)	0.0028 (11)	0.0034 (14)	0.0034 (11)
C2A	0.0294 (16)	0.0250 (12)	0.0385 (15)	0.0010 (12)	0.0009 (15)	0.0055 (16)
S21A	0.0831 (7)	0.0352 (4)	0.0326 (4)	−0.0001 (5)	0.0087 (6)	0.0047 (4)
N3A	0.0310 (16)	0.0243 (13)	0.0282 (16)	0.0003 (10)	−0.0001 (12)	0.0011 (10)
C4A	0.0272 (17)	0.0318 (17)	0.035 (2)	0.0013 (12)	−0.0018 (16)	0.0008 (13)
O41A	0.0522 (16)	0.0291 (11)	0.0384 (14)	0.0002 (10)	0.0035 (13)	0.0087 (9)
C5A	0.0306 (18)	0.0367 (14)	0.0306 (15)	0.0036 (13)	0.0007 (14)	−0.0023 (16)
C6A	0.0200 (17)	0.0330 (16)	0.0374 (19)	0.0043 (11)	−0.0011 (15)	−0.0050 (14)
C61A	0.039 (2)	0.0333 (17)	0.049 (2)	−0.0009 (14)	0.0036 (18)	−0.0099 (14)
C2B	0.020 (2)	0.033 (2)	0.030 (3)	0.000	0.010 (2)	0.000
N21B	0.038 (2)	0.0302 (18)	0.028 (2)	0.000	0.000 (2)	0.000
N3B	0.0312 (16)	0.0319 (13)	0.0321 (15)	0.0059 (11)	0.0026 (14)	0.0029 (11)
C4B	0.0272 (18)	0.0522 (19)	0.037 (2)	0.0118 (14)	0.0037 (16)	0.0097 (16)
N41B	0.046 (4)	0.035 (3)	0.042 (4)	0.008 (2)	−0.007 (3)	0.009 (3)
C5B	0.031 (3)	0.079 (4)	0.029 (3)	0.000	−0.006 (2)	0.000
C2C	0.027 (3)	0.026 (2)	0.029 (2)	0.000	0.004 (2)	0.000
N21C	0.033 (2)	0.029 (2)	0.058 (3)	0.000	0.018 (2)	0.000
N3C	0.0306 (16)	0.0253 (13)	0.0553 (19)	0.0011 (10)	0.0091 (15)	−0.0048 (12)
C4C	0.035 (2)	0.0377 (17)	0.062 (3)	0.0060 (14)	0.0078 (19)	−0.0164 (16)
N41C	0.034 (3)	0.035 (3)	0.052 (4)	0.004 (2)	0.012 (3)	−0.015 (3)
C5C	0.030 (3)	0.053 (3)	0.035 (3)	0.000	0.010 (3)	0.000

Geometric parameters (Å, º)

N1A—C2A	1.354 (4)	C4B—N41B	1.277 (6)
N1A—C6A	1.373 (5)	C4B—C5B	1.382 (4)
N1A—H1A	0.887 (18)	C4B—H4B	0.9500
C2A—N3A	1.357 (4)	N41B—H41B	0.87 (2)
C2A—S21A	1.666 (3)	N41B—H42B	0.87 (2)
N3A—C4A	1.376 (4)	C5B—C4B^i	1.382 (4)
N3A—H3A	0.904 (17)	C5B—H5B	0.9500
C4A—O41A	1.238 (4)	C2C—N21C	1.331 (6)
C4A—C5A	1.440 (4)	C2C—N3C^ii	1.342 (3)
C5A—C6A	1.343 (4)	C2C—N3C	1.342 (3)
C5A—H5A	0.9500	N21C—H21C	0.870 (18)
C6A—C61A	1.493 (4)	N3C—C4C	1.337 (4)
C61A—H61A	0.9800	C4C—N41C	1.346 (6)
C61A—H61B	0.9800	C4C—C5C	1.374 (4)
C61A—H61C	0.9800	C4C—H4C	0.9500
C2B—N21B	1.336 (6)	N41C—H41C	0.89 (2)
C2B—N3B^i	1.349 (3)	N41C—H42C	0.89 (2)
C2B—N3B	1.349 (3)	C5C—C4C^ii	1.374 (4)
N21B—H21B	0.859 (17)	C5C—H5C	0.9500
N3B—C4B	1.343 (4)
C2A—N1A—C6A	123.5 (2)	C4B—N3B—C2B	116.4 (3)
C2A—N1A—H1A	117 (2)	N41B—C4B—N3B	123.5 (4)
C6A—N1A—H1A	119 (2)	N41B—C4B—C5B	113.2 (4)
N1A—C2A—N3A	115.3 (3)	N3B—C4B—C5B	123.1 (3)
N1A—C2A—S21A	123.0 (2)	N3B—C4B—H4B	118.5
N3A—C2A—S21A	121.6 (2)	C5B—C4B—H4B	118.5
C2A—N3A—C4A	126.1 (2)	C4B—N41B—H41B	123 (5)
C2A—N3A—H3A	117 (2)	C4B—N41B—H42B	124 (5)
C4A—N3A—H3A	117 (2)	H41B—N41B—H42B	112 (7)
O41A—C4A—N3A	119.6 (3)	C4B—C5B—C4B^i	115.9 (5)
O41A—C4A—C5A	125.4 (3)	C4B—C5B—H5B	122.0
N3A—C4A—C5A	115.0 (3)	C4B^i—C5B—H5B	122.0
C6A—C5A—C4A	120.0 (3)	N21C—C2C—N3C^ii	117.7 (2)
C6A—C5A—H5A	120.0	N21C—C2C—N3C	117.7 (2)
C4A—C5A—H5A	120.0	N3C^ii—C2C—N3C	124.6 (4)
C5A—C6A—N1A	120.0 (3)	C2C—N21C—H21C	112 (2)
C5A—C6A—C61A	124.8 (3)	C4C—N3C—C2C	116.5 (3)
N1A—C6A—C61A	115.2 (3)	N3C—C4C—N41C	120.8 (4)
C6A—C61A—H61A	109.5	N3C—C4C—C5C	123.3 (3)
C6A—C61A—H61B	109.5	N41C—C4C—C5C	113.3 (4)
H61A—C61A—H61B	109.5	N3C—C4C—H4C	118.3
C6A—C61A—H61C	109.5	C5C—C4C—H4C	118.3
H61A—C61A—H61C	109.5	C4C—N41C—H41C	116 (5)
H61B—C61A—H61C	109.5	C4C—N41C—H42C	127 (4)
N21B—C2B—N3B^i	117.5 (2)	H41C—N41C—H42C	117 (6)
N21B—C2B—N3B	117.5 (2)	C4C—C5C—C4C^ii	115.5 (4)
N3B^i—C2B—N3B	125.0 (4)	C4C—C5C—H5C	122.3
C2B—N21B—H21B	119 (2)	C4C^ii—C5C—H5C	122.3
C6A—N1A—C2A—N3A	−1.5 (5)	N21B—C2B—N3B—C4B	179.7 (4)
C6A—N1A—C2A—S21A	179.1 (2)	N3B^i—C2B—N3B—C4B	−2.8 (6)
N1A—C2A—N3A—C4A	−0.9 (5)	C2B—N3B—C4B—N41B	−174.6 (4)
S21A—C2A—N3A—C4A	178.5 (3)	C2B—N3B—C4B—C5B	0.7 (5)
C2A—N3A—C4A—O41A	−177.7 (3)	N41B—C4B—C5B—C4B^i	176.8 (4)
C2A—N3A—C4A—C5A	3.1 (5)	N3B—C4B—C5B—C4B^i	1.1 (7)
O41A—C4A—C5A—C6A	177.9 (3)	N21C—C2C—N3C—C4C	−177.8 (4)
N3A—C4A—C5A—C6A	−3.0 (5)	N3C^ii—C2C—N3C—C4C	3.9 (6)
C4A—C5A—C6A—N1A	0.9 (5)	C2C—N3C—C4C—N41C	157.1 (5)
C4A—C5A—C6A—C61A	−178.4 (3)	C2C—N3C—C4C—C5C	−3.6 (6)
C2A—N1A—C6A—C5A	1.4 (5)	N3C—C4C—C5C—C4C^ii	3.3 (7)
C2A—N1A—C6A—C61A	−179.2 (3)	N41C—C4C—C5C—C4C^ii	−158.7 (4)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···N3C	0.89 (2)	2.00 (2)	2.883 (4)	171 (3)
N3A—H3A···N3B	0.90 (2)	1.97 (2)	2.868 (3)	174 (3)
N21B—H21B···O41A	0.86 (2)	2.16 (2)	2.993 (3)	164 (3)
N41B—H41B···S21A	0.87 (2)	2.47 (4)	3.258 (6)	150 (6)
N21C—H21C···O41A^iii	0.87 (2)	2.33 (2)	3.137 (3)	154 (3)
N41C—H41C···S21A	0.89 (2)	2.37 (2)	3.250 (6)	170 (6)

Symmetry code: (iii) −x+1, −y+1, −z+1.

(III) 6-Methyl-2-thiouracil–2,4-diaminopyrimidine–dimethylacetamide (2/1/2)

Crystal data

2C5H6N2OS·C4H6N4·2C4H9NO	Z = 2
Mr = 568.73	F(000) = 604
Triclinic, P1	Dx = 1.299 Mg m^−3
a = 8.2095 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.8069 (11) Å	Cell parameters from 12180 reflections
c = 14.3391 (13) Å	θ = 3.2–26.0°
α = 89.914 (7)°	µ = 0.23 mm^−1
β = 76.230 (7)°	T = 173 K
γ = 83.418 (7)°	Block, colourless
V = 1454.1 (2) Å^3	0.30 × 0.22 × 0.18 mm

Data collection

Stoe IPDS II two-circle diffractometer	4514 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.030
ω scans	θmax = 25.6°, θmin = 3.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→9
Tmin = 0.939, Tmax = 0.961	k = −15→15
11080 measured reflections	l = −14→17
5400 independent reflections

Refinement

Refinement on F^2	264 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0563P)^2 + 0.3449P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
5400 reflections	Δρmax = 0.34 e Å^−3
417 parameters	Δρmin = −0.26 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.45478 (17)	0.96529 (11)	0.63713 (10)	0.0274 (3)
H1A	0.410 (2)	1.0264 (13)	0.6207 (14)	0.033*
C2A	0.3567 (2)	0.88686 (12)	0.66301 (11)	0.0262 (3)
S21A	0.15266 (5)	0.90090 (3)	0.66124 (3)	0.03432 (13)
N3A	0.43471 (17)	0.79672 (11)	0.69065 (10)	0.0279 (3)
H3A	0.377 (2)	0.7436 (13)	0.7066 (14)	0.034*
C4A	0.6030 (2)	0.78048 (13)	0.69412 (12)	0.0296 (4)
O41A	0.66039 (15)	0.69456 (9)	0.71935 (10)	0.0400 (3)
C5A	0.6972 (2)	0.86709 (13)	0.66526 (12)	0.0309 (4)
H5A	0.8131	0.8615	0.6664	0.037*
C6A	0.6232 (2)	0.95624 (13)	0.63654 (12)	0.0287 (3)
C61A	0.7149 (2)	1.04783 (14)	0.60124 (14)	0.0366 (4)
H61A	0.8249	1.0398	0.6176	0.055*
H61B	0.6485	1.1127	0.6315	0.055*
H61C	0.7317	1.0512	0.5314	0.055*
N1B	0.53903 (17)	0.04939 (11)	0.86396 (10)	0.0296 (3)
H1B	0.501 (2)	−0.0102 (13)	0.8852 (14)	0.036*
C2B	0.4328 (2)	0.12959 (13)	0.84211 (12)	0.0282 (3)
S21B	0.22937 (5)	0.11895 (3)	0.85068 (4)	0.03592 (13)
N3B	0.50420 (17)	0.21859 (11)	0.81230 (11)	0.0301 (3)
H3B	0.439 (2)	0.2708 (13)	0.8008 (14)	0.036*
C4B	0.6731 (2)	0.23176 (14)	0.80270 (14)	0.0350 (4)
O41B	0.72348 (16)	0.31615 (10)	0.77527 (12)	0.0485 (4)
C5B	0.7756 (2)	0.14273 (14)	0.82645 (13)	0.0349 (4)
H5B	0.8928	0.1458	0.8204	0.042*
C6B	0.7077 (2)	0.05468 (13)	0.85730 (12)	0.0310 (4)
C61B	0.8046 (2)	−0.04043 (15)	0.88667 (14)	0.0395 (4)
H61D	0.9255	−0.0331	0.8686	0.059*
H61E	0.7833	−0.1030	0.8543	0.059*
H61F	0.7686	−0.0476	0.9564	0.059*
N1C	0.29400 (18)	0.40736 (12)	0.77383 (11)	0.0361 (3)
C2C	0.3541 (2)	0.50040 (13)	0.75200 (13)	0.0324 (4)
N21C	0.51981 (19)	0.50244 (13)	0.74292 (15)	0.0453 (4)
H21C	0.586 (3)	0.4483 (15)	0.7502 (17)	0.054*
H22C	0.562 (3)	0.5620 (15)	0.7349 (17)	0.054*
N3C	0.26437 (18)	0.59105 (12)	0.73741 (12)	0.0369 (3)
C4C	0.0981 (2)	0.58694 (16)	0.74605 (15)	0.0426 (4)
H4C	0.0290	0.6488	0.7364	0.051*	0.182 (5)
C5C	0.0240 (2)	0.49327 (17)	0.76904 (16)	0.0481 (5)
H5C	−0.0933	0.4907	0.7755	0.058*
C6C	0.1277 (2)	0.40755 (16)	0.78137 (15)	0.0408 (4)
H6C	0.0804	0.3435	0.7963	0.049*	0.818 (5)
N41C	0.0045 (3)	0.67242 (17)	0.7335 (2)	0.0594 (9)	0.818 (5)
H41C	0.054 (4)	0.7283 (19)	0.713 (2)	0.071*	0.818 (5)
H42C	−0.103 (3)	0.675 (3)	0.729 (2)	0.071*	0.818 (5)
N41'	0.0469 (11)	0.3370 (7)	0.7899 (8)	0.052 (3)	0.182 (5)
H41'	0.0954	0.2724	0.7921	0.062*	0.182 (5)
H42'	−0.0624	0.3486	0.7940	0.062*	0.182 (5)
C1X	0.0801 (3)	1.2088 (2)	0.5787 (2)	0.0658 (7)
H1XA	0.0125	1.2534	0.6329	0.099*	0.898 (4)
H1XB	0.0719	1.1347	0.5940	0.099*	0.898 (4)
H1XC	0.0377	1.2250	0.5214	0.099*	0.898 (4)
H1XD	−0.0361	1.2350	0.5772	0.099*	0.102 (4)
H1XE	0.0845	1.1906	0.6446	0.099*	0.102 (4)
H1XF	0.1184	1.1463	0.5365	0.099*	0.102 (4)
O21X	0.37568 (18)	1.16082 (10)	0.57009 (11)	0.0451 (3)
C31X	0.4755 (4)	1.34632 (19)	0.51789 (19)	0.0666 (7)
H3XA	0.5501	1.2800	0.5129	0.100*	0.898 (4)
H3XB	0.4851	1.3881	0.5731	0.100*	0.898 (4)
H3XC	0.5085	1.3857	0.4591	0.100*	0.898 (4)
H3XD	0.4106	1.4111	0.5040	0.100*	0.102 (4)
H3XE	0.5647	1.3228	0.4608	0.100*	0.102 (4)
H3XF	0.5266	1.3598	0.5713	0.100*	0.102 (4)
C32X	0.1741 (5)	1.4083 (2)	0.5147 (2)	0.0883 (10)
H4XA	0.1983	1.4255	0.4466	0.132*	0.898 (4)
H4XB	0.1772	1.4709	0.5533	0.132*	0.898 (4)
H4XC	0.0618	1.3846	0.5338	0.132*	0.898 (4)
H4XD	0.0558	1.4300	0.5146	0.132*	0.102 (4)
H4XE	0.2455	1.4153	0.4502	0.132*	0.102 (4)
H4XF	0.2082	1.4530	0.5604	0.132*	0.102 (4)
C1Y	0.1704 (3)	−0.1831 (2)	0.93008 (18)	0.0604 (6)
H1YA	0.1510	−0.2234	0.8765	0.091*	0.615 (6)
H1YB	0.1485	−0.1078	0.9193	0.091*	0.615 (6)
H1YC	0.0943	−0.2012	0.9901	0.091*	0.615 (6)
H1YD	0.0584	−0.2059	0.9365	0.091*	0.385 (6)
H1YE	0.2112	−0.1581	0.8650	0.091*	0.385 (6)
H1YF	0.1631	−0.1261	0.9769	0.091*	0.385 (6)
O21Y	0.46831 (18)	−0.15098 (10)	0.91848 (11)	0.0472 (3)
C31Y	0.5723 (4)	−0.3364 (2)	0.9634 (2)	0.0738 (8)
H3YA	0.6203	−0.3957	0.9184	0.111*	0.615 (6)
H3YB	0.5807	−0.3565	1.0283	0.111*	0.615 (6)
H3YC	0.6346	−0.2760	0.9441	0.111*	0.615 (6)
H3YD	0.5160	−0.4001	0.9772	0.111*	0.385 (6)
H3YE	0.6113	−0.3160	1.0195	0.111*	0.385 (6)
H3YF	0.6692	−0.3501	0.9082	0.111*	0.385 (6)
C32Y	0.2586 (4)	−0.38080 (18)	0.9845 (2)	0.0726 (8)
H4YA	0.3080	−0.4515	0.9594	0.109*	0.615 (6)
H4YB	0.1668	−0.3560	0.9540	0.109*	0.615 (6)
H4YC	0.2140	−0.3829	1.0541	0.109*	0.615 (6)
H4YD	0.1413	−0.3912	0.9869	0.109*	0.385 (6)
H4YE	0.2787	−0.3873	1.0490	0.109*	0.385 (6)
H4YF	0.3348	−0.4341	0.9412	0.109*	0.385 (6)
C2X	0.2632 (3)	1.22962 (17)	0.56005 (16)	0.0411 (6)	0.898 (4)
N3X	0.3016 (3)	1.32414 (15)	0.53055 (15)	0.0519 (6)	0.898 (4)
C2X'	0.3546 (12)	1.2584 (7)	0.5462 (14)	0.039 (4)	0.102 (4)
N3X'	0.1943 (12)	1.2935 (7)	0.5445 (12)	0.047 (4)	0.102 (4)
C2Y	0.3552 (5)	−0.2100 (3)	0.9370 (2)	0.0399 (10)	0.615 (6)
N3Y	0.3913 (5)	−0.3077 (2)	0.9629 (2)	0.0533 (11)	0.615 (6)
C2Y'	0.4457 (7)	−0.2458 (4)	0.9403 (4)	0.0376 (14)	0.385 (6)
N3Y'	0.2906 (6)	−0.2740 (3)	0.9483 (3)	0.0394 (14)	0.385 (6)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0250 (7)	0.0263 (7)	0.0307 (7)	−0.0047 (5)	−0.0057 (6)	0.0029 (5)
C2A	0.0243 (8)	0.0278 (8)	0.0260 (8)	−0.0042 (6)	−0.0045 (6)	0.0012 (6)
S21A	0.0208 (2)	0.0362 (2)	0.0467 (3)	−0.00462 (16)	−0.00888 (17)	0.01143 (18)
N3A	0.0217 (6)	0.0281 (7)	0.0352 (8)	−0.0068 (5)	−0.0075 (6)	0.0051 (6)
C4A	0.0231 (8)	0.0316 (8)	0.0349 (9)	−0.0047 (6)	−0.0083 (7)	0.0013 (7)
O41A	0.0268 (6)	0.0334 (6)	0.0644 (9)	−0.0068 (5)	−0.0187 (6)	0.0130 (6)
C5A	0.0226 (8)	0.0370 (9)	0.0355 (9)	−0.0094 (7)	−0.0088 (7)	0.0033 (7)
C6A	0.0271 (8)	0.0333 (8)	0.0270 (8)	−0.0101 (7)	−0.0058 (6)	−0.0006 (6)
C61A	0.0344 (9)	0.0376 (9)	0.0412 (10)	−0.0166 (7)	−0.0101 (8)	0.0078 (8)
N1B	0.0261 (7)	0.0292 (7)	0.0326 (8)	0.0000 (6)	−0.0066 (6)	0.0031 (6)
C2B	0.0258 (8)	0.0303 (8)	0.0272 (8)	0.0004 (6)	−0.0054 (6)	0.0006 (6)
S21B	0.0236 (2)	0.0369 (2)	0.0488 (3)	−0.00511 (16)	−0.01088 (18)	0.00844 (19)
N3B	0.0216 (7)	0.0285 (7)	0.0401 (8)	0.0006 (5)	−0.0087 (6)	0.0045 (6)
C4B	0.0252 (8)	0.0378 (9)	0.0415 (10)	−0.0025 (7)	−0.0078 (7)	0.0048 (8)
O41B	0.0280 (6)	0.0389 (7)	0.0796 (11)	−0.0065 (5)	−0.0136 (7)	0.0181 (7)
C5B	0.0208 (8)	0.0440 (10)	0.0395 (10)	0.0002 (7)	−0.0085 (7)	0.0061 (8)
C6B	0.0257 (8)	0.0371 (9)	0.0280 (8)	0.0036 (7)	−0.0057 (7)	0.0015 (7)
C61B	0.0312 (9)	0.0447 (10)	0.0403 (10)	0.0057 (8)	−0.0091 (8)	0.0080 (8)
N1C	0.0268 (7)	0.0376 (8)	0.0449 (9)	−0.0103 (6)	−0.0072 (6)	0.0021 (7)
C2C	0.0244 (8)	0.0352 (9)	0.0382 (10)	−0.0030 (7)	−0.0087 (7)	−0.0001 (7)
N21C	0.0238 (8)	0.0297 (8)	0.0857 (14)	−0.0057 (6)	−0.0184 (8)	0.0122 (8)
N3C	0.0239 (7)	0.0400 (8)	0.0488 (9)	−0.0042 (6)	−0.0122 (6)	0.0047 (7)
C4C	0.0268 (9)	0.0505 (11)	0.0528 (12)	−0.0008 (8)	−0.0158 (8)	0.0018 (9)
C5C	0.0245 (9)	0.0611 (13)	0.0605 (13)	−0.0124 (9)	−0.0103 (9)	−0.0022 (10)
C6C	0.0278 (9)	0.0450 (10)	0.0503 (12)	−0.0117 (8)	−0.0070 (8)	−0.0010 (8)
N41C	0.0265 (11)	0.0376 (12)	0.122 (2)	−0.0090 (8)	−0.0305 (12)	0.0301 (12)
N41'	0.033 (5)	0.027 (5)	0.097 (9)	−0.014 (4)	−0.015 (5)	0.014 (4)
C1X	0.0441 (12)	0.0692 (15)	0.0753 (17)	−0.0042 (11)	0.0017 (12)	−0.0036 (13)
O21X	0.0471 (8)	0.0323 (7)	0.0557 (9)	−0.0048 (6)	−0.0115 (7)	0.0110 (6)
C31X	0.0923 (19)	0.0496 (13)	0.0565 (14)	−0.0365 (13)	−0.0017 (13)	−0.0040 (11)
C32X	0.129 (3)	0.0474 (14)	0.0687 (17)	0.0378 (15)	−0.0078 (17)	0.0070 (12)
C1Y	0.0478 (12)	0.0782 (16)	0.0502 (13)	0.0146 (11)	−0.0123 (10)	−0.0041 (12)
O21Y	0.0451 (8)	0.0361 (7)	0.0594 (9)	−0.0040 (6)	−0.0108 (7)	0.0090 (6)
C31Y	0.0840 (18)	0.0663 (15)	0.0636 (16)	0.0371 (14)	−0.0245 (14)	−0.0060 (12)
C32Y	0.106 (2)	0.0439 (13)	0.0626 (16)	−0.0259 (13)	−0.0004 (15)	0.0096 (11)
C2X	0.0498 (14)	0.0354 (12)	0.0348 (12)	−0.0018 (10)	−0.0049 (10)	−0.0011 (9)
N3X	0.0697 (15)	0.0302 (10)	0.0496 (12)	0.0008 (10)	−0.0053 (11)	0.0049 (8)
C2X'	0.047 (7)	0.033 (7)	0.035 (9)	−0.008 (6)	−0.002 (8)	0.002 (7)
N3X'	0.053 (7)	0.035 (7)	0.045 (9)	0.016 (5)	−0.005 (8)	0.004 (6)
C2Y	0.049 (2)	0.034 (2)	0.0328 (17)	0.0020 (17)	−0.0048 (15)	0.0006 (13)
N3Y	0.070 (2)	0.0334 (18)	0.0508 (18)	0.0018 (16)	−0.0063 (16)	0.0079 (13)
C2Y'	0.045 (3)	0.026 (3)	0.036 (3)	0.008 (2)	−0.005 (2)	0.003 (2)
N3Y'	0.047 (3)	0.028 (2)	0.040 (2)	−0.005 (2)	−0.003 (2)	0.0068 (17)

Geometric parameters (Å, º)

N1A—C2A	1.355 (2)	C1X—H1XC	0.9800
N1A—C6A	1.372 (2)	C1X—H1XD	0.9800
N1A—H1A	0.882 (15)	C1X—H1XE	0.9800
C2A—N3A	1.360 (2)	C1X—H1XF	0.9800
C2A—S21A	1.6707 (16)	O21X—C2X	1.236 (3)
N3A—C4A	1.386 (2)	O21X—C2X'	1.298 (8)
N3A—H3A	0.872 (15)	C31X—N3X	1.457 (3)
C4A—O41A	1.235 (2)	C31X—C2X'	1.575 (8)
C4A—C5A	1.429 (2)	C31X—H3XA	0.9800
C5A—C6A	1.342 (2)	C31X—H3XB	0.9800
C5A—H5A	0.9500	C31X—H3XC	0.9800
C6A—C61A	1.490 (2)	C31X—H3XD	0.9800
C61A—H61A	0.9800	C31X—H3XE	0.9800
C61A—H61B	0.9800	C31X—H3XF	0.9800
C61A—H61C	0.9800	C32X—N3X	1.470 (3)
N1B—C2B	1.355 (2)	C32X—N3X'	1.532 (7)
N1B—C6B	1.374 (2)	C32X—H4XA	0.9800
N1B—H1B	0.883 (15)	C32X—H4XB	0.9800
C2B—N3B	1.363 (2)	C32X—H4XC	0.9800
C2B—S21B	1.6668 (17)	C32X—H4XD	0.9800
N3B—C4B	1.390 (2)	C32X—H4XE	0.9800
N3B—H3B	0.850 (15)	C32X—H4XF	0.9800
C4B—O41B	1.232 (2)	C1Y—N3Y'	1.502 (5)
C4B—C5B	1.428 (2)	C1Y—C2Y	1.543 (4)
C5B—C6B	1.343 (3)	C1Y—H1YA	0.9800
C5B—H5B	0.9500	C1Y—H1YB	0.9800
C6B—C61B	1.493 (2)	C1Y—H1YC	0.9800
C61B—H61D	0.9800	C1Y—H1YD	0.9800
C61B—H61E	0.9800	C1Y—H1YE	0.9800
C61B—H61F	0.9800	C1Y—H1YF	0.9800
N1C—C6C	1.343 (2)	O21Y—C2Y	1.243 (4)
N1C—C2C	1.349 (2)	O21Y—C2Y'	1.277 (5)
C2C—N21C	1.339 (2)	C31Y—N3Y	1.491 (4)
C2C—N3C	1.346 (2)	C31Y—C2Y'	1.556 (5)
N21C—H21C	0.853 (16)	C31Y—H3YA	0.9800
N21C—H22C	0.870 (16)	C31Y—H3YB	0.9800
N3C—C4C	1.348 (2)	C31Y—H3YC	0.9800
C4C—N41C	1.301 (3)	C31Y—H3YD	0.9800
C4C—C5C	1.410 (3)	C31Y—H3YE	0.9800
C4C—H4C	0.9500	C31Y—H3YF	0.9800
C5C—C6C	1.348 (3)	C32Y—N3Y'	1.491 (4)
C5C—H5C	0.9500	C32Y—N3Y	1.494 (4)
C6C—N41'	1.170 (8)	C32Y—H4YA	0.9800
C6C—H6C	0.9500	C32Y—H4YB	0.9800
N41C—H41C	0.880 (18)	C32Y—H4YC	0.9800
N41C—H42C	0.895 (18)	C32Y—H4YD	0.9800
N41'—H41'	0.8800	C32Y—H4YE	0.9800
N41'—H42'	0.8800	C32Y—H4YF	0.9800
C1X—N3X'	1.519 (8)	C2X—N3X	1.329 (3)
C1X—C2X	1.517 (3)	C2X'—N3X'	1.348 (9)
C1X—H1XA	0.9800	C2Y—N3Y	1.326 (5)
C1X—H1XB	0.9800	C2Y'—N3Y'	1.342 (7)
C2A—N1A—C6A	123.42 (14)	H1XE—C1X—H1XF	109.5
C2A—N1A—H1A	119.9 (13)	N3X—C31X—H3XA	109.5
C6A—N1A—H1A	116.7 (13)	N3X—C31X—H3XB	109.5
N1A—C2A—N3A	115.86 (14)	H3XA—C31X—H3XB	109.5
N1A—C2A—S21A	121.76 (12)	N3X—C31X—H3XC	109.5
N3A—C2A—S21A	122.39 (12)	H3XA—C31X—H3XC	109.5
C2A—N3A—C4A	125.09 (14)	H3XB—C31X—H3XC	109.5
C2A—N3A—H3A	119.0 (13)	C2X'—C31X—H3XD	109.5
C4A—N3A—H3A	115.9 (13)	C2X'—C31X—H3XE	109.5
O41A—C4A—N3A	119.27 (15)	H3XD—C31X—H3XE	109.5
O41A—C4A—C5A	125.37 (15)	C2X'—C31X—H3XF	109.5
N3A—C4A—C5A	115.34 (14)	H3XD—C31X—H3XF	109.5
C6A—C5A—C4A	120.49 (15)	H3XE—C31X—H3XF	109.5
C6A—C5A—H5A	119.8	N3X—C32X—H4XA	109.5
C4A—C5A—H5A	119.8	N3X—C32X—H4XB	109.5
C5A—C6A—N1A	119.78 (15)	H4XA—C32X—H4XB	109.5
C5A—C6A—C61A	123.54 (15)	N3X—C32X—H4XC	109.5
N1A—C6A—C61A	116.67 (15)	H4XA—C32X—H4XC	109.5
C6A—C61A—H61A	109.5	H4XB—C32X—H4XC	109.5
C6A—C61A—H61B	109.5	N3X'—C32X—H4XD	109.5
H61A—C61A—H61B	109.5	N3X'—C32X—H4XE	109.5
C6A—C61A—H61C	109.5	H4XD—C32X—H4XE	109.5
H61A—C61A—H61C	109.5	N3X'—C32X—H4XF	109.5
H61B—C61A—H61C	109.5	H4XD—C32X—H4XF	109.5
C2B—N1B—C6B	123.75 (15)	H4XE—C32X—H4XF	109.5
C2B—N1B—H1B	120.7 (13)	C2Y—C1Y—H1YA	109.5
C6B—N1B—H1B	115.6 (13)	C2Y—C1Y—H1YB	109.5
N1B—C2B—N3B	115.42 (14)	H1YA—C1Y—H1YB	109.5
N1B—C2B—S21B	121.90 (13)	C2Y—C1Y—H1YC	109.5
N3B—C2B—S21B	122.67 (12)	H1YA—C1Y—H1YC	109.5
C2B—N3B—C4B	125.31 (14)	H1YB—C1Y—H1YC	109.5
C2B—N3B—H3B	116.8 (14)	N3Y'—C1Y—H1YD	109.5
C4B—N3B—H3B	117.8 (14)	N3Y'—C1Y—H1YE	109.5
O41B—C4B—N3B	119.61 (15)	H1YD—C1Y—H1YE	109.5
O41B—C4B—C5B	125.10 (16)	N3Y'—C1Y—H1YF	109.5
N3B—C4B—C5B	115.29 (15)	H1YD—C1Y—H1YF	109.5
C6B—C5B—C4B	120.47 (16)	H1YE—C1Y—H1YF	109.5
C6B—C5B—H5B	119.8	N3Y—C31Y—H3YA	109.5
C4B—C5B—H5B	119.8	N3Y—C31Y—H3YB	109.5
C5B—C6B—N1B	119.74 (15)	H3YA—C31Y—H3YB	109.5
C5B—C6B—C61B	123.85 (16)	N3Y—C31Y—H3YC	109.5
N1B—C6B—C61B	116.40 (15)	H3YA—C31Y—H3YC	109.5
C6B—C61B—H61D	109.5	H3YB—C31Y—H3YC	109.5
C6B—C61B—H61E	109.5	C2Y'—C31Y—H3YD	109.5
H61D—C61B—H61E	109.5	C2Y'—C31Y—H3YE	109.5
C6B—C61B—H61F	109.5	H3YD—C31Y—H3YE	109.5
H61D—C61B—H61F	109.5	C2Y'—C31Y—H3YF	109.5
H61E—C61B—H61F	109.5	H3YD—C31Y—H3YF	109.5
C6C—N1C—C2C	115.34 (15)	H3YE—C31Y—H3YF	109.5
N21C—C2C—N3C	116.74 (16)	N3Y—C32Y—H4YA	109.5
N21C—C2C—N1C	116.75 (15)	N3Y—C32Y—H4YB	109.5
N3C—C2C—N1C	126.51 (16)	H4YA—C32Y—H4YB	109.5
C2C—N21C—H21C	122.8 (16)	N3Y—C32Y—H4YC	109.5
C2C—N21C—H22C	119.7 (16)	H4YA—C32Y—H4YC	109.5
H21C—N21C—H22C	117 (2)	H4YB—C32Y—H4YC	109.5
C2C—N3C—C4C	115.73 (16)	N3Y'—C32Y—H4YD	109.5
N41C—C4C—N3C	118.55 (19)	N3Y'—C32Y—H4YE	109.5
N41C—C4C—C5C	119.70 (18)	H4YD—C32Y—H4YE	109.5
N3C—C4C—C5C	121.75 (17)	N3Y'—C32Y—H4YF	109.5
N3C—C4C—H4C	119.1	H4YD—C32Y—H4YF	109.5
C5C—C4C—H4C	119.1	H4YE—C32Y—H4YF	109.5
C6C—C5C—C4C	116.82 (17)	O21X—C2X—N3X	120.0 (2)
C6C—C5C—H5C	121.6	O21X—C2X—C1X	121.7 (2)
C4C—C5C—H5C	121.6	N3X—C2X—C1X	118.3 (2)
N41'—C6C—N1C	129.6 (5)	C2X—N3X—C31X	118.4 (2)
N41'—C6C—C5C	106.2 (5)	C2X—N3X—C32X	122.6 (2)
N1C—C6C—C5C	123.86 (18)	C31X—N3X—C32X	119.0 (2)
N1C—C6C—H6C	118.1	O21X—C2X'—N3X'	113.9 (7)
C5C—C6C—H6C	118.1	O21X—C2X'—C31X	134.3 (7)
C4C—N41C—H41C	119 (2)	N3X'—C2X'—C31X	111.8 (6)
C4C—N41C—H42C	124 (2)	C2X'—N3X'—C1X	110.0 (6)
H41C—N41C—H42C	115 (3)	C2X'—N3X'—C32X	112.6 (6)
C6C—N41'—H41'	120.0	C1X—N3X'—C32X	137.2 (7)
C6C—N41'—H42'	120.0	O21Y—C2Y—N3Y	119.5 (4)
H41'—N41'—H42'	120.0	O21Y—C2Y—C1Y	126.6 (3)
C2X—C1X—H1XA	109.5	N3Y—C2Y—C1Y	113.9 (3)
C2X—C1X—H1XB	109.5	C2Y—N3Y—C31Y	114.2 (3)
H1XA—C1X—H1XB	109.5	C2Y—N3Y—C32Y	120.8 (3)
C2X—C1X—H1XC	109.5	C31Y—N3Y—C32Y	125.0 (3)
H1XA—C1X—H1XC	109.5	O21Y—C2Y'—N3Y'	117.7 (5)
H1XB—C1X—H1XC	109.5	O21Y—C2Y'—C31Y	129.4 (4)
N3X'—C1X—H1XD	109.5	N3Y'—C2Y'—C31Y	112.9 (4)
N3X'—C1X—H1XE	109.5	C2Y'—N3Y'—C32Y	117.8 (4)
H1XD—C1X—H1XE	109.5	C2Y'—N3Y'—C1Y	111.2 (4)
N3X'—C1X—H1XF	109.5	C32Y—N3Y'—C1Y	130.4 (4)
H1XD—C1X—H1XF	109.5
C6A—N1A—C2A—N3A	1.0 (2)	O21X—C2X—N3X—C32X	178.3 (2)
C6A—N1A—C2A—S21A	−179.18 (13)	C1X—C2X—N3X—C32X	−0.5 (3)
N1A—C2A—N3A—C4A	0.1 (2)	C2X'—C31X—N3X—C2X	1.7 (12)
S21A—C2A—N3A—C4A	−179.65 (13)	C2X'—C31X—N3X—C32X	178.8 (12)
C2A—N3A—C4A—O41A	−179.10 (16)	N3X'—C32X—N3X—C2X	−1.5 (11)
C2A—N3A—C4A—C5A	−0.4 (2)	N3X'—C32X—N3X—C31X	−178.5 (12)
O41A—C4A—C5A—C6A	178.13 (17)	C2X—O21X—C2X'—N3X'	−2.4 (9)
N3A—C4A—C5A—C6A	−0.5 (2)	C2X—O21X—C2X'—C31X	178 (3)
C4A—C5A—C6A—N1A	1.6 (3)	N3X—C31X—C2X'—O21X	179 (3)
C4A—C5A—C6A—C61A	−177.10 (16)	N3X—C31X—C2X'—N3X'	−0.9 (9)
C2A—N1A—C6A—C5A	−1.9 (3)	O21X—C2X'—N3X'—C1X	4 (2)
C2A—N1A—C6A—C61A	176.85 (15)	C31X—C2X'—N3X'—C1X	−176.1 (11)
C6B—N1B—C2B—N3B	0.0 (2)	O21X—C2X'—N3X'—C32X	−179.2 (12)
C6B—N1B—C2B—S21B	179.57 (13)	C31X—C2X'—N3X'—C32X	0 (2)
N1B—C2B—N3B—C4B	0.3 (3)	C2X—C1X—N3X'—C2X'	−0.8 (9)
S21B—C2B—N3B—C4B	−179.26 (14)	C2X—C1X—N3X'—C32X	−176 (3)
C2B—N3B—C4B—O41B	−179.81 (17)	N3X—C32X—N3X'—C2X'	0.5 (9)
C2B—N3B—C4B—C5B	0.2 (3)	N3X—C32X—N3X'—C1X	176 (3)
O41B—C4B—C5B—C6B	178.87 (19)	C2Y'—O21Y—C2Y—N3Y	4.4 (4)
N3B—C4B—C5B—C6B	−1.2 (3)	C2Y'—O21Y—C2Y—C1Y	−173.5 (6)
C4B—C5B—C6B—N1B	1.5 (3)	N3Y'—C1Y—C2Y—O21Y	173.4 (5)
C4B—C5B—C6B—C61B	−177.88 (17)	N3Y'—C1Y—C2Y—N3Y	−4.6 (3)
C2B—N1B—C6B—C5B	−0.9 (3)	O21Y—C2Y—N3Y—C31Y	−1.9 (4)
C2B—N1B—C6B—C61B	178.53 (16)	C1Y—C2Y—N3Y—C31Y	176.2 (2)
C6C—N1C—C2C—N21C	−179.27 (18)	O21Y—C2Y—N3Y—C32Y	−179.3 (3)
C6C—N1C—C2C—N3C	−0.1 (3)	C1Y—C2Y—N3Y—C32Y	−1.2 (4)
N21C—C2C—N3C—C4C	179.41 (18)	C2Y'—C31Y—N3Y—C2Y	−2.5 (4)
N1C—C2C—N3C—C4C	0.2 (3)	C2Y'—C31Y—N3Y—C32Y	174.8 (5)
C2C—N3C—C4C—N41C	179.5 (2)	N3Y'—C32Y—N3Y—C2Y	5.8 (3)
C2C—N3C—C4C—C5C	0.1 (3)	N3Y'—C32Y—N3Y—C31Y	−171.3 (5)
N41C—C4C—C5C—C6C	−179.8 (2)	C2Y—O21Y—C2Y'—N3Y'	3.9 (3)
N3C—C4C—C5C—C6C	−0.5 (3)	C2Y—O21Y—C2Y'—C31Y	−173.6 (8)
C2C—N1C—C6C—N41'	171.6 (8)	N3Y—C31Y—C2Y'—O21Y	172.3 (7)
C2C—N1C—C6C—C5C	−0.4 (3)	N3Y—C31Y—C2Y'—N3Y'	−5.2 (3)
C4C—C5C—C6C—N41'	−172.9 (6)	O21Y—C2Y'—N3Y'—C32Y	−173.2 (4)
C4C—C5C—C6C—N1C	0.6 (3)	C31Y—C2Y'—N3Y'—C32Y	4.7 (6)
C2X'—O21X—C2X—N3X	1.5 (14)	O21Y—C2Y'—N3Y'—C1Y	−0.6 (6)
C2X'—O21X—C2X—C1X	−179.7 (14)	C31Y—C2Y'—N3Y'—C1Y	177.2 (3)
N3X'—C1X—C2X—O21X	−176.9 (11)	N3Y—C32Y—N3Y'—C2Y'	1.6 (3)
N3X'—C1X—C2X—N3X	1.9 (11)	N3Y—C32Y—N3Y'—C1Y	−169.2 (6)
O21X—C2X—N3X—C31X	−4.7 (3)	C2Y—C1Y—N3Y'—C2Y'	−2.7 (3)
C1X—C2X—N3X—C31X	176.5 (2)	C2Y—C1Y—N3Y'—C32Y	168.7 (6)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21X	0.88 (2)	1.89 (2)	2.7447 (19)	165 (2)
N3A—H3A···N3C	0.87 (2)	2.26 (2)	3.120 (2)	171 (2)
N1B—H1B···O21Y	0.88 (2)	1.90 (2)	2.766 (2)	168 (2)
N3B—H3B···N1C	0.85 (2)	2.09 (2)	2.936 (2)	175 (2)
N21C—H21C···O41B	0.85 (2)	2.01 (2)	2.856 (2)	175 (2)
N21C—H22C···O41A	0.87 (2)	1.95 (2)	2.822 (2)	178 (2)
N41C—H41C···S21A	0.88 (2)	2.49 (2)	3.365 (2)	172 (3)
N41C—H42C···O41A^i	0.90 (2)	1.97 (2)	2.862 (2)	174 (3)
N41′—H41′···S21B	0.88	2.39	3.234 (9)	161
N41′—H42′···O41B^i	0.88	1.93	2.755 (9)	155

Symmetry code: (i) x−1, y, z.

(IV) 6-Methyl-2-thiouracil–2,4-diaminopyrimidine–dimethylformamide (2/1/2)

Crystal data

C5H6N2OS·0.5C4H6N4·C3H7NO	F(000) = 1144
Mr = 270.34	Dx = 1.315 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.9786 (15) Å	Cell parameters from 10267 reflections
b = 8.2010 (11) Å	θ = 3.5–26.3°
c = 22.568 (2) Å	µ = 0.24 mm^−1
β = 99.899 (8)°	T = 173 K
V = 2731.0 (5) Å^3	Needle, colourless
Z = 8	0.55 × 0.15 × 0.09 mm

Data collection

Stoe IPDS II two-circle diffractometer	2026 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.047
ω scans	θmax = 25.9°, θmin = 3.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −18→18
Tmin = 0.957, Tmax = 0.980	k = −10→10
10452 measured reflections	l = −24→27
2624 independent reflections

Refinement

Refinement on F^2	5 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.095	w = 1/[σ^2(Fo^2) + (0.0476P)^2 + 0.6173P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
2624 reflections	Δρmax = 0.19 e Å^−3
188 parameters	Δρmin = −0.18 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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.62272 (9)	0.34325 (19)	0.50684 (7)	0.0338 (3)
H1A	0.6395 (13)	0.389 (2)	0.4755 (8)	0.041*
C2A	0.60075 (11)	0.4457 (2)	0.54928 (9)	0.0313 (4)
S21A	0.61329 (3)	0.64761 (6)	0.54377 (2)	0.03786 (15)
N3A	0.56941 (10)	0.37360 (17)	0.59575 (7)	0.0331 (3)
H3A	0.5556 (13)	0.437 (2)	0.6244 (8)	0.040*
C4A	0.55733 (13)	0.2068 (2)	0.60169 (10)	0.0400 (5)
O41A	0.52625 (12)	0.15493 (18)	0.64540 (7)	0.0580 (4)
C5A	0.58231 (13)	0.1089 (2)	0.55504 (10)	0.0410 (5)
H5A	0.5763	−0.0063	0.5565	0.049*
C6A	0.61419 (11)	0.1779 (2)	0.50923 (9)	0.0358 (4)
C61A	0.64137 (14)	0.0844 (3)	0.45808 (11)	0.0466 (5)
H61A	0.6409	−0.0327	0.4668	0.070*	0.66 (3)
H61B	0.7024	0.1173	0.4529	0.070*	0.66 (3)
H61C	0.5985	0.1073	0.4211	0.070*	0.66 (3)
H61D	0.5935	0.0063	0.4424	0.070*	0.34 (3)
H61E	0.6979	0.0255	0.4723	0.070*	0.34 (3)
H61F	0.6504	0.1602	0.4261	0.070*	0.34 (3)
C2B	0.5000	0.4900 (3)	0.7500	0.0380 (6)
N21B	0.5000	0.3266 (3)	0.7500	0.0427 (6)
H21B	0.5127 (15)	0.277 (3)	0.7184 (8)	0.051*
N3B	0.52076 (11)	0.5639 (2)	0.70080 (9)	0.0435 (4)
C4B	0.51911 (14)	0.7282 (3)	0.70231 (12)	0.0536 (6)
H4B	0.5320	0.7861	0.6683	0.064*	0.5
N41B	0.5344 (3)	0.8133 (4)	0.66147 (17)	0.0455 (8)	0.5
H41B	0.551 (3)	0.756 (5)	0.6331 (16)	0.055*	0.5
H42B	0.532 (3)	0.920 (2)	0.662 (2)	0.055*	0.5
C5B	0.5000	0.8159 (4)	0.7500	0.0678 (11)
H5B	0.5000	0.9318	0.7500	0.081*
C1X	0.68279 (14)	0.5927 (3)	0.39205 (10)	0.0460 (5)
H1X	0.6630	0.6715	0.4178	0.055*
O11X	0.68408 (10)	0.4498 (2)	0.40787 (7)	0.0516 (4)
N2X	0.70698 (11)	0.6454 (2)	0.34158 (8)	0.0484 (4)
C3X	0.73637 (17)	0.5313 (4)	0.29970 (12)	0.0666 (7)
H3X1	0.7282	0.4195	0.3131	0.100*
H3X2	0.8005	0.5499	0.2981	0.100*
H3X3	0.7003	0.5475	0.2596	0.100*
C4X	0.70508 (18)	0.8165 (3)	0.32632 (12)	0.0634 (7)
H4X1	0.6791	0.8785	0.3564	0.095*
H4X2	0.6679	0.8325	0.2866	0.095*
H4X3	0.7669	0.8546	0.3257	0.095*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0355 (7)	0.0297 (8)	0.0371 (9)	−0.0013 (6)	0.0091 (6)	−0.0058 (7)
C2A	0.0314 (8)	0.0275 (9)	0.0340 (10)	0.0002 (7)	0.0026 (7)	−0.0044 (8)
S21A	0.0507 (3)	0.0242 (2)	0.0401 (3)	−0.0029 (2)	0.0118 (2)	−0.0011 (2)
N3A	0.0456 (8)	0.0205 (8)	0.0343 (9)	−0.0013 (6)	0.0102 (7)	−0.0038 (7)
C4A	0.0531 (11)	0.0250 (9)	0.0430 (12)	0.0002 (8)	0.0115 (9)	−0.0037 (9)
O41A	0.1016 (12)	0.0265 (7)	0.0541 (10)	−0.0058 (7)	0.0366 (9)	−0.0036 (7)
C5A	0.0503 (10)	0.0235 (9)	0.0500 (13)	0.0018 (7)	0.0112 (9)	−0.0071 (8)
C6A	0.0332 (8)	0.0288 (9)	0.0447 (12)	0.0013 (7)	0.0051 (8)	−0.0107 (8)
C61A	0.0488 (11)	0.0407 (11)	0.0528 (14)	−0.0012 (9)	0.0155 (10)	−0.0167 (10)
C2B	0.0381 (13)	0.0214 (13)	0.0498 (18)	0.000	−0.0056 (12)	0.000
N21B	0.0738 (16)	0.0206 (11)	0.0343 (14)	0.000	0.0111 (12)	0.000
N3B	0.0463 (9)	0.0239 (8)	0.0563 (12)	−0.0015 (6)	−0.0020 (8)	0.0096 (8)
C4B	0.0505 (12)	0.0244 (10)	0.0792 (18)	−0.0050 (8)	−0.0080 (11)	0.0150 (11)
N41B	0.079 (2)	0.0212 (17)	0.042 (2)	0.0013 (15)	0.0258 (18)	0.0043 (15)
C5B	0.067 (2)	0.0153 (15)	0.110 (3)	0.000	−0.015 (2)	0.000
C1X	0.0486 (11)	0.0559 (14)	0.0358 (12)	−0.0037 (9)	0.0136 (9)	−0.0060 (10)
O11X	0.0609 (9)	0.0505 (10)	0.0462 (9)	−0.0003 (7)	0.0175 (7)	−0.0010 (7)
N2X	0.0528 (9)	0.0610 (12)	0.0338 (10)	−0.0094 (9)	0.0145 (8)	−0.0070 (9)
C3X	0.0637 (14)	0.094 (2)	0.0473 (15)	−0.0027 (14)	0.0253 (12)	−0.0166 (14)
C4X	0.0738 (15)	0.0708 (18)	0.0463 (14)	−0.0179 (13)	0.0122 (11)	0.0082 (12)

Geometric parameters (Å, º)

N1A—C2A	1.356 (2)	N21B—H21B	0.868 (15)
N1A—C6A	1.364 (2)	N3B—C4B	1.348 (3)
N1A—H1A	0.874 (15)	C4B—N41B	1.209 (4)
C2A—N3A	1.356 (2)	C4B—C5B	1.365 (3)
C2A—S21A	1.6735 (18)	C4B—H4B	0.9500
N3A—C4A	1.390 (2)	N41B—H41B	0.870 (19)
N3A—H3A	0.882 (15)	N41B—H42B	0.878 (19)
C4A—O41A	1.236 (2)	C5B—C4B^i	1.365 (3)
C4A—C5A	1.424 (3)	C5B—H5B	0.9500
C5A—C6A	1.337 (3)	C1X—O11X	1.225 (3)
C5A—H5A	0.9500	C1X—N2X	1.326 (3)
C6A—C61A	1.499 (3)	C1X—H1X	0.9500
C61A—H61A	0.9800	N2X—C4X	1.444 (3)
C61A—H61B	0.9800	N2X—C3X	1.451 (3)
C61A—H61C	0.9800	C3X—H3X1	0.9800
C61A—H61D	0.9800	C3X—H3X2	0.9800
C61A—H61E	0.9800	C3X—H3X3	0.9800
C61A—H61F	0.9800	C4X—H4X1	0.9800
C2B—N21B	1.340 (3)	C4X—H4X2	0.9800
C2B—N3B^i	1.347 (2)	C4X—H4X3	0.9800
C2B—N3B	1.347 (2)
C2A—N1A—C6A	123.52 (17)	N3B^i—C2B—N3B	126.5 (3)
C2A—N1A—H1A	116.4 (14)	C2B—N21B—H21B	117.7 (16)
C6A—N1A—H1A	120.0 (14)	C2B—N3B—C4B	114.9 (2)
N1A—C2A—N3A	115.73 (16)	N41B—C4B—N3B	123.5 (3)
N1A—C2A—S21A	121.10 (15)	N41B—C4B—C5B	112.9 (2)
N3A—C2A—S21A	123.17 (14)	N3B—C4B—C5B	123.6 (2)
C2A—N3A—C4A	124.90 (16)	N3B—C4B—H4B	118.2
C2A—N3A—H3A	117.9 (14)	C5B—C4B—H4B	118.2
C4A—N3A—H3A	117.2 (14)	C4B—N41B—H41B	111 (3)
O41A—C4A—N3A	119.26 (18)	C4B—N41B—H42B	124 (3)
O41A—C4A—C5A	125.37 (18)	H41B—N41B—H42B	125 (5)
N3A—C4A—C5A	115.36 (18)	C4B—C5B—C4B^i	116.4 (3)
C6A—C5A—C4A	120.51 (18)	C4B—C5B—H5B	121.8
C6A—C5A—H5A	119.7	C4B^i—C5B—H5B	121.8
C4A—C5A—H5A	119.7	O11X—C1X—N2X	124.7 (2)
C5A—C6A—N1A	119.97 (17)	O11X—C1X—H1X	117.6
C5A—C6A—C61A	124.02 (18)	N2X—C1X—H1X	117.6
N1A—C6A—C61A	116.01 (18)	C1X—N2X—C4X	121.65 (19)
C6A—C61A—H61A	109.5	C1X—N2X—C3X	120.5 (2)
C6A—C61A—H61B	109.5	C4X—N2X—C3X	117.8 (2)
H61A—C61A—H61B	109.5	N2X—C3X—H3X1	109.5
C6A—C61A—H61C	109.5	N2X—C3X—H3X2	109.5
H61A—C61A—H61C	109.5	H3X1—C3X—H3X2	109.5
H61B—C61A—H61C	109.5	N2X—C3X—H3X3	109.5
C6A—C61A—H61D	109.5	H3X1—C3X—H3X3	109.5
C6A—C61A—H61E	109.5	H3X2—C3X—H3X3	109.5
H61D—C61A—H61E	109.5	N2X—C4X—H4X1	109.5
C6A—C61A—H61F	109.5	N2X—C4X—H4X2	109.5
H61D—C61A—H61F	109.5	H4X1—C4X—H4X2	109.5
H61E—C61A—H61F	109.5	N2X—C4X—H4X3	109.5
N21B—C2B—N3B^i	116.74 (13)	H4X1—C4X—H4X3	109.5
N21B—C2B—N3B	116.74 (13)	H4X2—C4X—H4X3	109.5
C6A—N1A—C2A—N3A	0.3 (3)	C2A—N1A—C6A—C5A	0.3 (3)
C6A—N1A—C2A—S21A	179.73 (14)	C2A—N1A—C6A—C61A	179.69 (16)
N1A—C2A—N3A—C4A	−1.2 (3)	N21B—C2B—N3B—C4B	179.35 (13)
S21A—C2A—N3A—C4A	179.43 (15)	N3B^i—C2B—N3B—C4B	−0.65 (13)
C2A—N3A—C4A—O41A	−178.34 (19)	C2B—N3B—C4B—N41B	−178.6 (3)
C2A—N3A—C4A—C5A	1.3 (3)	C2B—N3B—C4B—C5B	1.4 (3)
O41A—C4A—C5A—C6A	179.1 (2)	N41B—C4B—C5B—C4B^i	179.2 (3)
N3A—C4A—C5A—C6A	−0.5 (3)	N3B—C4B—C5B—C4B^i	−0.73 (14)
C4A—C5A—C6A—N1A	−0.2 (3)	O11X—C1X—N2X—C4X	−179.0 (2)
C4A—C5A—C6A—C61A	−179.52 (18)	O11X—C1X—N2X—C3X	1.1 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O11X	0.87 (2)	1.84 (2)	2.702 (2)	170 (2)
N3A—H3A···N3B	0.88 (2)	2.15 (2)	3.030 (3)	173 (2)
N21B—H21B···O41A	0.87 (2)	1.97 (2)	2.8335 (19)	173 (2)
N41B—H41B···S21A	0.87 (2)	2.52 (2)	3.373 (3)	167 (4)
N41B—H42B···O41A^ii	0.88 (2)	1.96 (2)	2.825 (4)	168 (5)

Symmetry code: (ii) x, y+1, z.

(V) 2,4,6-Triaminopyrimidinium 6-methyl-2-thiouracilate–6-methyl-2-thiouracil–dimethylformamide (1/1/1)

Crystal data

C4H8N5^+·C5H5N2OS^−·C5H6N2OS·2C3H7NO	F(000) = 588
Mr = 555.69	Dx = 1.367 Mg m^−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
a = 8.2680 (8) Å	Cell parameters from 20998 reflections
b = 6.6000 (4) Å	θ = 2.5–26.5°
c = 25.043 (2) Å	µ = 0.25 mm^−1
β = 98.887 (7)°	T = 173 K
V = 1350.16 (19) Å^3	Block, colourless
Z = 2	0.38 × 0.32 × 0.18 mm

Data collection

Stoe IPDS II two-circle diffractometer	2588 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.032
ω scans	θmax = 25.9°, θmin = 2.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→9
Tmin = 0.912, Tmax = 0.956	k = −8→8
10981 measured reflections	l = −30→30
2836 independent reflections

Refinement

Refinement on F^2	10 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.102	w = 1/[σ^2(Fo^2) + (0.0434P)^2 + 0.6067P] where P = (Fo^2 + 2Fc^2)/3
S = 1.15	(Δ/σ)max < 0.001
2836 reflections	Δρmax = 0.23 e Å^−3
244 parameters	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.

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.2568 (2)	0.2500	−0.07376 (8)	0.0303 (4)
H1A	0.277 (3)	0.2500	−0.1073 (8)	0.036*
C2A	0.3805 (3)	0.2500	−0.03157 (9)	0.0277 (5)
S21A	0.57544 (7)	0.2500	−0.04155 (2)	0.03333 (17)
N3A	0.3343 (2)	0.2500	0.01840 (8)	0.0285 (4)
H3A	0.416 (3)	0.2500	0.0454 (9)	0.034*
C4A	0.1757 (3)	0.2500	0.02881 (9)	0.0305 (5)
O41A	0.14919 (19)	0.2500	0.07611 (6)	0.0387 (4)
C5A	0.0527 (3)	0.2500	−0.01817 (9)	0.0336 (5)
H5A	−0.0598	0.2500	−0.0142	0.040*
C6A	0.0955 (3)	0.2500	−0.06796 (9)	0.0313 (5)
C61A	−0.0246 (3)	0.2500	−0.11931 (10)	0.0403 (6)
H61A	−0.1363	0.2500	−0.1107	0.060*	0.74 (3)
H62A	−0.0080	0.1288	−0.1404	0.060*	0.368 (16)
H63A	−0.0080	0.3712	−0.1404	0.060*	0.368 (16)
H64A	0.0347	0.2500	−0.1503	0.060*	0.26 (3)
H65A	−0.0935	0.3712	−0.1206	0.060*	0.132 (16)
H66A	−0.0935	0.1288	−0.1206	0.060*	0.132 (16)
N1B	0.4998 (2)	0.2500	0.42379 (7)	0.0303 (4)
H1B	0.558 (3)	0.2500	0.4559 (8)	0.036*
C2B	0.5791 (3)	0.2500	0.37962 (9)	0.0302 (5)
S21B	0.78692 (7)	0.2500	0.39207 (2)	0.0458 (2)
N3B	0.4938 (2)	0.2500	0.32940 (7)	0.0302 (4)
C4B	0.3265 (3)	0.2500	0.32283 (9)	0.0304 (5)
O41B	0.24638 (19)	0.2500	0.27568 (6)	0.0378 (4)
C5B	0.2457 (3)	0.2500	0.36933 (9)	0.0335 (5)
H5B	0.1295	0.2500	0.3650	0.040*
C6B	0.3340 (3)	0.2500	0.41956 (9)	0.0300 (5)
C61B	0.2622 (3)	0.2500	0.47071 (9)	0.0377 (6)
H61B	0.1425	0.2500	0.4621	0.056*
H62B	0.2985	0.3712	0.4918	0.056*	0.5
H63B	0.2985	0.1288	0.4918	0.056*	0.5
N1C	0.5835 (2)	0.2500	0.12805 (7)	0.0278 (4)
C2C	0.5317 (3)	0.2500	0.17556 (9)	0.0276 (5)
N21C	0.3722 (2)	0.2500	0.17763 (8)	0.0369 (5)
H21C	0.306 (3)	0.2500	0.1463 (9)	0.044*
H22C	0.330 (3)	0.2500	0.2071 (9)	0.044*
N3C	0.6346 (2)	0.2500	0.22384 (8)	0.0292 (4)
H3C	0.591 (3)	0.2500	0.2541 (8)	0.035*
C4C	0.8009 (3)	0.2500	0.22510 (9)	0.0296 (5)
N41C	0.8946 (2)	0.2500	0.27300 (8)	0.0406 (5)
H41C	0.854 (4)	0.2500	0.3032 (9)	0.049*
H42C	1.000 (2)	0.2500	0.2727 (13)	0.049*
C5C	0.8600 (3)	0.2500	0.17666 (9)	0.0297 (5)
H5C	0.9745	0.2500	0.1758	0.036*
C6C	0.7485 (3)	0.2500	0.12902 (9)	0.0274 (5)
N61C	0.8005 (2)	0.2500	0.08109 (8)	0.0341 (5)
H61C	0.905 (2)	0.2500	0.0787 (12)	0.041*
H62C	0.728 (3)	0.2500	0.0523 (9)	0.041*
C1X	0.4470 (3)	0.2500	−0.18893 (10)	0.0350 (5)
H1X	0.5350	0.2500	−0.1597	0.042*
O11X	0.3073 (2)	0.2500	−0.17780 (7)	0.0406 (4)
N2X	0.4844 (3)	0.2500	−0.23839 (8)	0.0357 (5)
C3X	0.3574 (3)	0.2500	−0.28540 (10)	0.0452 (7)
H3X1	0.2497	0.2500	−0.2736	0.068*
H3X2	0.3684	0.1288	−0.3071	0.068*	0.5
H3X3	0.3684	0.3712	−0.3071	0.068*	0.5
C4X	0.6536 (3)	0.2500	−0.24770 (12)	0.0480 (7)
H4X1	0.7266	0.2500	−0.2129	0.072*
H4X2	0.6742	0.3712	−0.2682	0.072*	0.5
H4X3	0.6742	0.1288	−0.2682	0.072*	0.5
C1Y	0.7031 (3)	0.2500	0.58127 (10)	0.0376 (6)
H1Y	0.6457	0.2500	0.6113	0.045*
O11Y	0.6206 (2)	0.2500	0.53625 (7)	0.0456 (5)
N2Y	0.8650 (2)	0.2500	0.59181 (8)	0.0365 (5)
C3Y	0.9650 (3)	0.2500	0.54872 (11)	0.0452 (7)
H3Y1	0.8937	0.2500	0.5136	0.068*
H3Y2	1.0342	0.1288	0.5518	0.068*	0.5
H3Y3	1.0342	0.3712	0.5518	0.068*	0.5
C4Y	0.9517 (3)	0.2500	0.64663 (10)	0.0495 (7)
H4Y1	0.8726	0.2500	0.6720	0.074*
H4Y2	1.0205	0.3712	0.6525	0.074*	0.5
H4Y3	1.0205	0.1288	0.6525	0.074*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0256 (9)	0.0436 (11)	0.0224 (9)	0.000	0.0057 (8)	0.000
C2A	0.0264 (11)	0.0317 (11)	0.0256 (11)	0.000	0.0057 (9)	0.000
S21A	0.0223 (3)	0.0524 (4)	0.0263 (3)	0.000	0.0072 (2)	0.000
N3A	0.0213 (9)	0.0415 (11)	0.0228 (9)	0.000	0.0038 (7)	0.000
C4A	0.0242 (11)	0.0417 (13)	0.0259 (11)	0.000	0.0051 (9)	0.000
O41A	0.0226 (8)	0.0714 (12)	0.0227 (8)	0.000	0.0058 (6)	0.000
C5A	0.0197 (10)	0.0520 (14)	0.0292 (12)	0.000	0.0043 (9)	0.000
C6A	0.0245 (11)	0.0408 (13)	0.0285 (12)	0.000	0.0032 (9)	0.000
C61A	0.0296 (12)	0.0621 (17)	0.0282 (12)	0.000	0.0015 (10)	0.000
N1B	0.0229 (9)	0.0478 (12)	0.0195 (9)	0.000	0.0017 (7)	0.000
C2B	0.0247 (11)	0.0436 (13)	0.0220 (10)	0.000	0.0030 (8)	0.000
S21B	0.0198 (3)	0.0935 (6)	0.0240 (3)	0.000	0.0027 (2)	0.000
N3B	0.0209 (9)	0.0473 (12)	0.0225 (9)	0.000	0.0036 (7)	0.000
C4B	0.0230 (11)	0.0420 (13)	0.0264 (11)	0.000	0.0040 (9)	0.000
O41B	0.0224 (8)	0.0685 (12)	0.0220 (8)	0.000	0.0017 (6)	0.000
C5B	0.0203 (10)	0.0549 (15)	0.0257 (11)	0.000	0.0046 (9)	0.000
C6B	0.0238 (11)	0.0422 (13)	0.0251 (11)	0.000	0.0068 (9)	0.000
C61B	0.0260 (11)	0.0639 (17)	0.0241 (11)	0.000	0.0071 (9)	0.000
N1C	0.0193 (9)	0.0415 (11)	0.0228 (9)	0.000	0.0038 (7)	0.000
C2C	0.0220 (10)	0.0376 (12)	0.0233 (10)	0.000	0.0032 (8)	0.000
N21C	0.0199 (9)	0.0691 (15)	0.0222 (9)	0.000	0.0049 (7)	0.000
N3C	0.0203 (9)	0.0461 (11)	0.0218 (9)	0.000	0.0046 (7)	0.000
C4C	0.0218 (10)	0.0413 (13)	0.0250 (11)	0.000	0.0018 (8)	0.000
N41C	0.0204 (9)	0.0797 (17)	0.0212 (10)	0.000	0.0015 (8)	0.000
C5C	0.0186 (10)	0.0455 (13)	0.0251 (11)	0.000	0.0040 (8)	0.000
C6C	0.0231 (10)	0.0354 (12)	0.0244 (10)	0.000	0.0060 (8)	0.000
N61C	0.0208 (9)	0.0600 (13)	0.0220 (9)	0.000	0.0048 (7)	0.000
C1X	0.0365 (13)	0.0415 (13)	0.0266 (11)	0.000	0.0035 (10)	0.000
O11X	0.0358 (10)	0.0577 (11)	0.0295 (9)	0.000	0.0088 (7)	0.000
N2X	0.0342 (11)	0.0480 (12)	0.0255 (10)	0.000	0.0061 (8)	0.000
C3X	0.0481 (16)	0.0606 (17)	0.0254 (12)	0.000	0.0010 (11)	0.000
C4X	0.0405 (15)	0.0672 (19)	0.0391 (14)	0.000	0.0153 (12)	0.000
C1Y	0.0326 (12)	0.0541 (16)	0.0261 (12)	0.000	0.0052 (10)	0.000
O11Y	0.0375 (10)	0.0692 (13)	0.0276 (9)	0.000	−0.0029 (7)	0.000
N2Y	0.0299 (10)	0.0583 (13)	0.0214 (9)	0.000	0.0041 (8)	0.000
C3Y	0.0368 (14)	0.0691 (19)	0.0316 (13)	0.000	0.0118 (11)	0.000
C4Y	0.0403 (14)	0.081 (2)	0.0253 (12)	0.000	−0.0018 (11)	0.000

Geometric parameters (Å, º)

N1A—C2A	1.352 (3)	N21C—H21C	0.883 (18)
N1A—C6A	1.364 (3)	N21C—H22C	0.862 (17)
N1A—H1A	0.883 (17)	N3C—C4C	1.370 (3)
C2A—N3A	1.364 (3)	N3C—H3C	0.886 (17)
C2A—S21A	1.669 (2)	C4C—N41C	1.324 (3)
N3A—C4A	1.376 (3)	C4C—C5C	1.376 (3)
N3A—H3A	0.878 (17)	N41C—H41C	0.872 (18)
C4A—O41A	1.237 (3)	N41C—H42C	0.869 (18)
C4A—C5A	1.432 (3)	C5C—C6C	1.391 (3)
C5A—C6A	1.348 (3)	C5C—H5C	0.9500
C5A—H5A	0.9500	C6C—N61C	1.336 (3)
C6A—C61A	1.499 (3)	N61C—H61C	0.872 (17)
C61A—H61A	0.9800	N61C—H62C	0.862 (17)
C61A—H62A	0.9800	C1X—O11X	1.229 (3)
C61A—H63A	0.9800	C1X—N2X	1.322 (3)
C61A—H64A	0.9800	C1X—H1X	0.9500
C61A—H65A	0.9800	N2X—C3X	1.451 (3)
C61A—H66A	0.9800	N2X—C4X	1.453 (3)
N1B—C6B	1.358 (3)	C3X—H3X1	0.9800
N1B—C2B	1.370 (3)	C3X—H3X2	0.9800
N1B—H1B	0.872 (17)	C3X—H3X3	0.9800
C2B—N3B	1.344 (3)	C4X—H4X1	0.9800
C2B—S21B	1.698 (2)	C4X—H4X2	0.9800
N3B—C4B	1.367 (3)	C4X—H4X3	0.9800
C4B—O41B	1.262 (3)	C1Y—O11Y	1.224 (3)
C4B—C5B	1.429 (3)	C1Y—N2Y	1.324 (3)
C5B—C6B	1.353 (3)	C1Y—H1Y	0.9500
C5B—H5B	0.9500	N2Y—C4Y	1.447 (3)
C6B—C61B	1.493 (3)	N2Y—C3Y	1.457 (3)
C61B—H61B	0.9800	C3Y—H3Y1	0.9800
C61B—H62B	0.9800	C3Y—H3Y2	0.9800
C61B—H63B	0.9800	C3Y—H3Y3	0.9800
N1C—C2C	1.325 (3)	C4Y—H4Y1	0.9800
N1C—C6C	1.360 (3)	C4Y—H4Y2	0.9800
C2C—N21C	1.328 (3)	C4Y—H4Y3	0.9800
C2C—N3C	1.367 (3)
C2A—N1A—C6A	123.41 (19)	C2C—N21C—H22C	124 (2)
C2A—N1A—H1A	120.7 (18)	H21C—N21C—H22C	119 (3)
C6A—N1A—H1A	115.9 (18)	C2C—N3C—C4C	120.37 (19)
N1A—C2A—N3A	115.59 (19)	C2C—N3C—H3C	118.5 (18)
N1A—C2A—S21A	120.95 (17)	C4C—N3C—H3C	121.2 (18)
N3A—C2A—S21A	123.46 (17)	N41C—C4C—N3C	117.7 (2)
C2A—N3A—C4A	125.75 (19)	N41C—C4C—C5C	124.1 (2)
C2A—N3A—H3A	114.7 (18)	N3C—C4C—C5C	118.1 (2)
C4A—N3A—H3A	119.5 (18)	C4C—N41C—H41C	123 (2)
O41A—C4A—N3A	119.7 (2)	C4C—N41C—H42C	116 (2)
O41A—C4A—C5A	125.4 (2)	H41C—N41C—H42C	122 (3)
N3A—C4A—C5A	114.9 (2)	C4C—C5C—C6C	118.5 (2)
C6A—C5A—C4A	120.4 (2)	C4C—C5C—H5C	120.7
C6A—C5A—H5A	119.8	C6C—C5C—H5C	120.7
C4A—C5A—H5A	119.8	N61C—C6C—N1C	116.4 (2)
C5A—C6A—N1A	120.0 (2)	N61C—C6C—C5C	120.5 (2)
C5A—C6A—C61A	124.0 (2)	N1C—C6C—C5C	123.0 (2)
N1A—C6A—C61A	116.0 (2)	C6C—N61C—H61C	121.3 (19)
C6A—C61A—H61A	109.5	C6C—N61C—H62C	118.3 (19)
C6A—C61A—H62A	109.5	H61C—N61C—H62C	120 (3)
H61A—C61A—H62A	109.5	O11X—C1X—N2X	125.2 (2)
C6A—C61A—H63A	109.5	O11X—C1X—H1X	117.4
H61A—C61A—H63A	109.5	N2X—C1X—H1X	117.4
H62A—C61A—H63A	109.5	C1X—N2X—C3X	121.0 (2)
C6A—C61A—H64A	109.5	C1X—N2X—C4X	121.4 (2)
C6A—C61A—H65A	109.5	C3X—N2X—C4X	117.6 (2)
H64A—C61A—H65A	109.5	N2X—C3X—H3X1	109.5
C6A—C61A—H66A	109.5	N2X—C3X—H3X2	109.5
H64A—C61A—H66A	109.5	H3X1—C3X—H3X2	109.5
H65A—C61A—H66A	109.5	N2X—C3X—H3X3	109.5
C6B—N1B—C2B	122.68 (19)	H3X1—C3X—H3X3	109.5
C6B—N1B—H1B	118.8 (18)	H3X2—C3X—H3X3	109.5
C2B—N1B—H1B	118.5 (18)	N2X—C4X—H4X1	109.5
N3B—C2B—N1B	120.5 (2)	N2X—C4X—H4X2	109.5
N3B—C2B—S21B	122.82 (17)	H4X1—C4X—H4X2	109.5
N1B—C2B—S21B	116.65 (17)	N2X—C4X—H4X3	109.5
C2B—N3B—C4B	119.20 (19)	H4X1—C4X—H4X3	109.5
O41B—C4B—N3B	119.2 (2)	H4X2—C4X—H4X3	109.5
O41B—C4B—C5B	121.2 (2)	O11Y—C1Y—N2Y	125.9 (2)
N3B—C4B—C5B	119.6 (2)	O11Y—C1Y—H1Y	117.1
C6B—C5B—C4B	120.3 (2)	N2Y—C1Y—H1Y	117.1
C6B—C5B—H5B	119.9	C1Y—N2Y—C4Y	121.8 (2)
C4B—C5B—H5B	119.9	C1Y—N2Y—C3Y	121.6 (2)
C5B—C6B—N1B	117.7 (2)	C4Y—N2Y—C3Y	116.6 (2)
C5B—C6B—C61B	124.6 (2)	N2Y—C3Y—H3Y1	109.5
N1B—C6B—C61B	117.6 (2)	N2Y—C3Y—H3Y2	109.5
C6B—C61B—H61B	109.5	H3Y1—C3Y—H3Y2	109.5
C6B—C61B—H62B	109.5	N2Y—C3Y—H3Y3	109.5
H61B—C61B—H62B	109.5	H3Y1—C3Y—H3Y3	109.5
C6B—C61B—H63B	109.5	H3Y2—C3Y—H3Y3	109.5
H61B—C61B—H63B	109.5	N2Y—C4Y—H4Y1	109.5
H62B—C61B—H63B	109.5	N2Y—C4Y—H4Y2	109.5
C2C—N1C—C6C	116.51 (19)	H4Y1—C4Y—H4Y2	109.5
N1C—C2C—N21C	119.7 (2)	N2Y—C4Y—H4Y3	109.5
N1C—C2C—N3C	123.41 (19)	H4Y1—C4Y—H4Y3	109.5
N21C—C2C—N3C	116.9 (2)	H4Y2—C4Y—H4Y3	109.5
C2C—N21C—H21C	116.5 (19)
C6A—N1A—C2A—N3A	0.000 (1)	C4B—C5B—C6B—N1B	0.000 (1)
C6A—N1A—C2A—S21A	180.000 (1)	C4B—C5B—C6B—C61B	180.000 (1)
N1A—C2A—N3A—C4A	0.000 (1)	C2B—N1B—C6B—C5B	0.000 (1)
S21A—C2A—N3A—C4A	180.000 (1)	C2B—N1B—C6B—C61B	180.000 (1)
C2A—N3A—C4A—O41A	180.000 (1)	C6C—N1C—C2C—N21C	180.000 (1)
C2A—N3A—C4A—C5A	0.000 (1)	C6C—N1C—C2C—N3C	0.000 (1)
O41A—C4A—C5A—C6A	180.000 (1)	N1C—C2C—N3C—C4C	0.000 (1)
N3A—C4A—C5A—C6A	0.000 (1)	N21C—C2C—N3C—C4C	180.000 (1)
C4A—C5A—C6A—N1A	0.000 (1)	C2C—N3C—C4C—N41C	180.000 (1)
C4A—C5A—C6A—C61A	180.000 (1)	C2C—N3C—C4C—C5C	0.000 (1)
C2A—N1A—C6A—C5A	0.000 (1)	N41C—C4C—C5C—C6C	180.000 (1)
C2A—N1A—C6A—C61A	180.000 (1)	N3C—C4C—C5C—C6C	0.000 (1)
C6B—N1B—C2B—N3B	0.000 (1)	C2C—N1C—C6C—N61C	180.000 (1)
C6B—N1B—C2B—S21B	180.000 (1)	C2C—N1C—C6C—C5C	0.000 (1)
N1B—C2B—N3B—C4B	0.000 (1)	C4C—C5C—C6C—N61C	180.000 (1)
S21B—C2B—N3B—C4B	180.000 (1)	C4C—C5C—C6C—N1C	0.000 (1)
C2B—N3B—C4B—O41B	180.000 (1)	O11X—C1X—N2X—C3X	0.000 (1)
C2B—N3B—C4B—C5B	0.000 (1)	O11X—C1X—N2X—C4X	180.000 (1)
O41B—C4B—C5B—C6B	180.000 (1)	O11Y—C1Y—N2Y—C4Y	180.000 (1)
N3B—C4B—C5B—C6B	0.000 (1)	O11Y—C1Y—N2Y—C3Y	0.000 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O11X	0.88 (2)	1.82 (2)	2.701 (2)	177 (3)
N3A—H3A···N1C	0.88 (2)	2.31 (2)	3.169 (3)	167 (2)
N1B—H1B···O11Y	0.87 (2)	2.00 (2)	2.839 (3)	162 (3)
N21C—H21C···O41A	0.88 (2)	2.02 (2)	2.901 (3)	178 (3)
N21C—H22C···O41B	0.86 (2)	1.95 (2)	2.811 (3)	177 (3)
N3C—H3C···N3B	0.89 (2)	2.16 (2)	3.049 (3)	178 (2)
N41C—H41C···S21B	0.87 (2)	2.38 (2)	3.241 (2)	171 (3)
N41C—H42C···O41B^i	0.87 (2)	2.03 (2)	2.899 (3)	177 (3)
N61C—H61C···O41A^i	0.87 (2)	2.03 (2)	2.905 (3)	178 (3)
N61C—H62C···S21A	0.86 (2)	2.49 (2)	3.336 (2)	167 (3)

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

(VI) 6-Methyl-2-thiouracil–6-amino-3H-isocytosine–dimethylformamide (1/1/1)

Crystal data

C5H6N2OS·C4H6N4O·C3H7NO	F(000) = 720
Mr = 341.40	Dx = 1.398 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.3559 (6) Å	Cell parameters from 22989 reflections
b = 30.068 (2) Å	θ = 2.9–26.6°
c = 8.1263 (7) Å	µ = 0.23 mm^−1
β = 115.534 (6)°	T = 173 K
V = 1621.8 (2) Å^3	Plate, colourless
Z = 4	0.40 × 0.28 × 0.13 mm

Data collection

Stoe IPDS II two-circle diffractometer	2686 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.088
ω scans	θmax = 26.0°, θmin = 2.9°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→9
Tmin = 0.925, Tmax = 0.970	k = −30→36
12580 measured reflections	l = −9→9
3119 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.047	w = 1/[σ^2(Fo^2) + (0.0752P)^2 + 0.1661P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.137	(Δ/σ)max = 0.014
S = 1.05	Δρmax = 0.17 e Å^−3
3119 reflections	Δρmin = −0.35 e Å^−3
233 parameters	Extinction correction: SHELXL3013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
7 restraints	Extinction coefficient: 0.052 (7)

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.

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

	x	y	z	Uiso*/Ueq
N1A	0.2107 (2)	0.54021 (5)	0.4616 (2)	0.0554 (4)
H1A	0.251 (3)	0.5675 (6)	0.509 (3)	0.066*
C2A	0.3094 (3)	0.50515 (6)	0.5672 (3)	0.0530 (4)
S21A	0.49426 (7)	0.51197 (2)	0.77513 (6)	0.0581 (2)
N3A	0.2427 (2)	0.46423 (5)	0.4922 (2)	0.0541 (4)
H3A	0.299 (3)	0.4400 (6)	0.554 (3)	0.065*
C4A	0.0902 (3)	0.45657 (7)	0.3188 (2)	0.0557 (4)
O41A	0.0453 (2)	0.41783 (5)	0.26477 (19)	0.0653 (4)
C5A	−0.0046 (3)	0.49538 (7)	0.2173 (3)	0.0575 (5)
H5A	−0.1105	0.4925	0.0981	0.069*
C6A	0.0551 (3)	0.53614 (7)	0.2898 (3)	0.0551 (4)
C61A	−0.0394 (3)	0.57872 (7)	0.1971 (3)	0.0631 (5)
H61A	−0.1280	0.5728	0.0685	0.095*
H62A	0.0662	0.5997	0.2055	0.095*
H63A	−0.1184	0.5915	0.2565	0.095*
N1B	0.4222 (2)	0.37462 (5)	0.6930 (2)	0.0550 (4)
C2B	0.3594 (3)	0.33685 (6)	0.6026 (2)	0.0549 (4)
N21B	0.1890 (3)	0.33560 (6)	0.4491 (2)	0.0655 (5)
H21B	0.134 (3)	0.3602 (7)	0.398 (3)	0.079*
H22B	0.156 (4)	0.3102 (6)	0.390 (3)	0.079*
N3B	0.4586 (2)	0.29747 (5)	0.6611 (2)	0.0565 (4)
H3B	0.414 (3)	0.2741 (6)	0.599 (3)	0.068*
C4B	0.6353 (3)	0.29360 (6)	0.8200 (3)	0.0561 (4)
O41B	0.7139 (2)	0.25554 (4)	0.86180 (19)	0.0660 (4)
C5B	0.7038 (3)	0.33296 (6)	0.9179 (3)	0.0580 (5)
H5B	0.8246	0.3332	1.0278	0.070*
C6B	0.5933 (3)	0.37189 (6)	0.8530 (3)	0.0556 (4)
N61B	0.6496 (3)	0.40973 (6)	0.9491 (2)	0.0651 (4)
H61B	0.762 (3)	0.4107 (9)	1.050 (3)	0.078*
H62B	0.584 (3)	0.4339 (7)	0.902 (3)	0.078*
C1X	0.4567 (3)	0.63490 (7)	0.7106 (3)	0.0667 (5)
H1X	0.5494	0.6114	0.7657	0.080*
O11X	0.2964 (2)	0.62540 (5)	0.5798 (2)	0.0749 (4)
N2X	0.5098 (3)	0.67515 (6)	0.7803 (2)	0.0653 (4)
C3X	0.3752 (4)	0.71295 (8)	0.7054 (3)	0.0759 (6)
H3X1	0.2581	0.7037	0.5947	0.114*
H3X2	0.4469	0.7368	0.6755	0.114*
H3X3	0.3303	0.7238	0.7955	0.114*
C4X	0.7010 (4)	0.68336 (8)	0.9354 (3)	0.0778 (6)
H4X1	0.7822	0.6561	0.9654	0.117*
H4X2	0.6772	0.6924	1.0403	0.117*
H4X3	0.7730	0.7071	0.9052	0.117*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0544 (8)	0.0506 (9)	0.0552 (8)	−0.0006 (7)	0.0179 (7)	−0.0015 (7)
C2A	0.0502 (9)	0.0524 (10)	0.0546 (10)	0.0015 (7)	0.0209 (8)	0.0007 (8)
S21A	0.0547 (3)	0.0545 (3)	0.0537 (3)	−0.00083 (19)	0.0127 (2)	−0.00218 (19)
N3A	0.0509 (8)	0.0521 (8)	0.0504 (8)	0.0008 (6)	0.0134 (6)	−0.0001 (7)
C4A	0.0489 (9)	0.0570 (11)	0.0537 (10)	−0.0004 (8)	0.0149 (8)	−0.0012 (8)
O41A	0.0647 (7)	0.0531 (8)	0.0586 (8)	−0.0028 (6)	0.0081 (6)	−0.0025 (6)
C5A	0.0509 (10)	0.0599 (11)	0.0530 (10)	0.0011 (8)	0.0140 (8)	0.0021 (8)
C6A	0.0490 (9)	0.0585 (11)	0.0539 (9)	0.0023 (8)	0.0184 (7)	0.0031 (8)
C61A	0.0592 (10)	0.0586 (12)	0.0629 (11)	0.0046 (9)	0.0182 (9)	0.0078 (9)
N1B	0.0512 (8)	0.0499 (9)	0.0537 (8)	0.0005 (6)	0.0131 (6)	−0.0025 (7)
C2B	0.0522 (9)	0.0509 (10)	0.0548 (10)	0.0015 (8)	0.0168 (8)	0.0003 (8)
N21B	0.0608 (9)	0.0510 (9)	0.0605 (10)	0.0026 (7)	0.0032 (8)	−0.0046 (7)
N3B	0.0575 (8)	0.0459 (8)	0.0550 (9)	0.0003 (7)	0.0136 (7)	−0.0015 (7)
C4B	0.0546 (9)	0.0515 (10)	0.0543 (10)	0.0033 (8)	0.0162 (8)	0.0040 (8)
O41B	0.0675 (8)	0.0501 (8)	0.0642 (8)	0.0063 (6)	0.0130 (7)	0.0036 (6)
C5B	0.0529 (9)	0.0536 (10)	0.0554 (10)	0.0010 (8)	0.0118 (8)	0.0002 (8)
C6B	0.0515 (9)	0.0540 (10)	0.0548 (10)	0.0000 (7)	0.0166 (8)	−0.0012 (8)
N61B	0.0631 (10)	0.0499 (9)	0.0606 (9)	0.0024 (7)	0.0063 (7)	−0.0048 (8)
C1X	0.0697 (11)	0.0565 (12)	0.0688 (12)	−0.0006 (9)	0.0250 (10)	0.0011 (9)
O11X	0.0744 (9)	0.0587 (9)	0.0747 (9)	−0.0031 (7)	0.0162 (8)	−0.0049 (7)
N2X	0.0682 (10)	0.0522 (9)	0.0685 (10)	−0.0018 (7)	0.0230 (9)	0.0008 (7)
C3X	0.0808 (14)	0.0574 (12)	0.0858 (15)	0.0056 (10)	0.0326 (12)	0.0029 (11)
C4X	0.0769 (14)	0.0702 (14)	0.0735 (14)	−0.0124 (11)	0.0202 (11)	−0.0011 (11)

Geometric parameters (Å, º)

N1A—C2A	1.356 (2)	N3B—C4B	1.387 (2)
N1A—C6A	1.377 (2)	N3B—H3B	0.846 (16)
N1A—H1A	0.901 (16)	C4B—O41B	1.261 (2)
C2A—N3A	1.367 (2)	C4B—C5B	1.394 (3)
C2A—S21A	1.6631 (19)	C5B—C6B	1.393 (3)
N3A—C4A	1.391 (2)	C5B—H5B	0.9500
N3A—H3A	0.882 (16)	C6B—N61B	1.341 (2)
C4A—O41A	1.238 (2)	N61B—H61B	0.879 (16)
C4A—C5A	1.425 (3)	N61B—H62B	0.865 (16)
C5A—C6A	1.349 (3)	C1X—O11X	1.233 (3)
C5A—H5A	0.9500	C1X—N2X	1.322 (3)
C6A—C61A	1.496 (3)	C1X—H1X	0.9500
C61A—H61A	0.9800	N2X—C4X	1.449 (3)
C61A—H62A	0.9800	N2X—C3X	1.457 (3)
C61A—H63A	0.9800	C3X—H3X1	0.9800
N1B—C2B	1.323 (2)	C3X—H3X2	0.9800
N1B—C6B	1.368 (2)	C3X—H3X3	0.9800
C2B—N21B	1.334 (2)	C4X—H4X1	0.9800
C2B—N3B	1.364 (2)	C4X—H4X2	0.9800
N21B—H21B	0.861 (16)	C4X—H4X3	0.9800
N21B—H22B	0.880 (16)
C2A—N1A—C6A	123.85 (17)	C2B—N3B—H3B	120.1 (16)
C2A—N1A—H1A	116.7 (15)	C4B—N3B—H3B	117.0 (16)
C6A—N1A—H1A	119.5 (15)	O41B—C4B—N3B	117.63 (17)
N1A—C2A—N3A	115.23 (16)	O41B—C4B—C5B	127.30 (17)
N1A—C2A—S21A	121.85 (15)	N3B—C4B—C5B	115.05 (17)
N3A—C2A—S21A	122.91 (14)	C4B—C5B—C6B	119.27 (17)
C2A—N3A—C4A	125.35 (16)	C4B—C5B—H5B	120.4
C2A—N3A—H3A	119.9 (15)	C6B—C5B—H5B	120.4
C4A—N3A—H3A	114.8 (15)	N61B—C6B—N1B	115.43 (17)
O41A—C4A—N3A	119.34 (17)	N61B—C6B—C5B	120.61 (17)
O41A—C4A—C5A	125.17 (17)	N1B—C6B—C5B	123.95 (17)
N3A—C4A—C5A	115.49 (17)	C6B—N61B—H61B	120.0 (17)
C6A—C5A—C4A	120.35 (17)	C6B—N61B—H62B	119.0 (17)
C6A—C5A—H5A	119.8	H61B—N61B—H62B	120 (2)
C4A—C5A—H5A	119.8	O11X—C1X—N2X	125.3 (2)
C5A—C6A—N1A	119.69 (18)	O11X—C1X—H1X	117.4
C5A—C6A—C61A	124.37 (18)	N2X—C1X—H1X	117.4
N1A—C6A—C61A	115.93 (18)	C1X—N2X—C4X	121.71 (19)
C6A—C61A—H61A	109.5	C1X—N2X—C3X	120.87 (19)
C6A—C61A—H62A	109.5	C4X—N2X—C3X	117.41 (18)
H61A—C61A—H62A	109.5	N2X—C3X—H3X1	109.5
C6A—C61A—H63A	109.5	N2X—C3X—H3X2	109.5
H61A—C61A—H63A	109.5	H3X1—C3X—H3X2	109.5
H62A—C61A—H63A	109.5	N2X—C3X—H3X3	109.5
C2B—N1B—C6B	115.73 (15)	H3X1—C3X—H3X3	109.5
N1B—C2B—N21B	120.36 (17)	H3X2—C3X—H3X3	109.5
N1B—C2B—N3B	123.04 (16)	N2X—C4X—H4X1	109.5
N21B—C2B—N3B	116.57 (17)	N2X—C4X—H4X2	109.5
C2B—N21B—H21B	119.2 (17)	H4X1—C4X—H4X2	109.5
C2B—N21B—H22B	117.7 (17)	N2X—C4X—H4X3	109.5
H21B—N21B—H22B	121 (2)	H4X1—C4X—H4X3	109.5
C2B—N3B—C4B	122.90 (16)	H4X2—C4X—H4X3	109.5
C6A—N1A—C2A—N3A	−0.6 (3)	C6B—N1B—C2B—N3B	−1.0 (3)
C6A—N1A—C2A—S21A	−179.11 (13)	N1B—C2B—N3B—C4B	−0.6 (3)
N1A—C2A—N3A—C4A	2.1 (3)	N21B—C2B—N3B—C4B	−178.78 (18)
S21A—C2A—N3A—C4A	−179.43 (14)	C2B—N3B—C4B—O41B	179.61 (17)
C2A—N3A—C4A—O41A	178.78 (17)	C2B—N3B—C4B—C5B	0.8 (3)
C2A—N3A—C4A—C5A	−2.0 (3)	O41B—C4B—C5B—C6B	−178.02 (19)
O41A—C4A—C5A—C6A	179.51 (18)	N3B—C4B—C5B—C6B	0.6 (3)
N3A—C4A—C5A—C6A	0.3 (3)	C2B—N1B—C6B—N61B	−176.36 (17)
C4A—C5A—C6A—N1A	1.0 (3)	C2B—N1B—C6B—C5B	2.6 (3)
C4A—C5A—C6A—C61A	−177.78 (17)	C4B—C5B—C6B—N61B	176.47 (19)
C2A—N1A—C6A—C5A	−0.9 (3)	C4B—C5B—C6B—N1B	−2.4 (3)
C2A—N1A—C6A—C61A	178.01 (16)	O11X—C1X—N2X—C4X	179.6 (2)
C6B—N1B—C2B—N21B	177.02 (17)	O11X—C1X—N2X—C3X	0.8 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O11X	0.90 (2)	1.82 (2)	2.713 (2)	172 (2)
N3A—H3A···N1B	0.88 (2)	2.25 (2)	3.132 (2)	175 (2)
N21B—H21B···O41A	0.86 (2)	2.00 (2)	2.848 (2)	170 (2)
N21B—H22B···O41B^i	0.88 (2)	2.06 (2)	2.856 (2)	151 (2)
N3B—H3B···O41B^i	0.85 (2)	2.06 (2)	2.815 (2)	149 (2)
N61B—H61B···O41A^ii	0.88 (2)	2.07 (2)	2.945 (2)	172 (2)
N61B—H62B···S21A	0.87 (2)	2.53 (2)	3.3708 (18)	163 (2)

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

(VII) 6-Methyl-2-thiouracil–6-amino-3H-isocytosine–dimethyl sulfoxide (1/1/1)

Crystal data

C5H6N2OS·C4H6N4O·C2H6OS	F(000) = 728
Mr = 346.43	Dx = 1.452 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.2520 (7) Å	Cell parameters from 20193 reflections
b = 23.9532 (19) Å	θ = 1.7–26.9°
c = 8.2133 (6) Å	µ = 0.36 mm^−1
β = 102.496 (6)°	T = 173 K
V = 1585.0 (2) Å^3	Plate, colourless
Z = 4	0.22 × 0.21 × 0.07 mm

Data collection

Stoe IPDS II two-circle diffractometer	2706 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.064
ω scans	θmax = 26.4°, θmin = 1.7°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→10
Tmin = 0.925, Tmax = 0.978	k = −29→29
13609 measured reflections	l = −10→9
3229 independent reflections

Refinement

Refinement on F^2	7 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.113	w = 1/[σ^2(Fo^2) + (0.0541P)^2 + 0.7321P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
3229 reflections	Δρmax = 0.35 e Å^−3
223 parameters	Δρmin = −0.32 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.

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

	x	y	z	Uiso*/Ueq
N1A	0.1018 (2)	0.42641 (8)	0.3836 (2)	0.0318 (4)
H1A	0.040 (3)	0.4003 (9)	0.416 (3)	0.038*
C2A	0.1819 (3)	0.46132 (9)	0.5040 (3)	0.0299 (5)
S21A	0.17565 (8)	0.45203 (3)	0.70382 (7)	0.03718 (17)
N3A	0.2681 (2)	0.50357 (8)	0.4504 (2)	0.0301 (4)
H3A	0.322 (3)	0.5273 (10)	0.524 (3)	0.036*
C4A	0.2767 (3)	0.51298 (10)	0.2863 (3)	0.0315 (5)
O41A	0.3617 (2)	0.55224 (7)	0.2531 (2)	0.0420 (4)
C5A	0.1840 (3)	0.47532 (10)	0.1667 (3)	0.0317 (5)
H5A	0.1814	0.4803	0.0514	0.038*
C6A	0.1002 (3)	0.43267 (10)	0.2175 (3)	0.0318 (5)
C61A	0.0057 (3)	0.38987 (11)	0.1041 (3)	0.0410 (6)
H61A	−0.0019	0.4012	−0.0120	0.061*
H62A	−0.1061	0.3864	0.1255	0.061*
H63A	0.0630	0.3539	0.1241	0.061*
N1B	0.4607 (2)	0.59726 (7)	0.6794 (2)	0.0282 (4)
C2B	0.5110 (2)	0.64257 (9)	0.6119 (3)	0.0262 (4)
N21B	0.5132 (3)	0.64312 (8)	0.4500 (2)	0.0330 (4)
H21B	0.473 (3)	0.6137 (9)	0.392 (3)	0.040*
H22B	0.540 (3)	0.6742 (9)	0.412 (3)	0.040*
N3B	0.5615 (2)	0.68989 (7)	0.6991 (2)	0.0276 (4)
H3B	0.589 (3)	0.7197 (9)	0.643 (3)	0.033*
C4B	0.5641 (3)	0.69499 (9)	0.8685 (3)	0.0267 (4)
O41B	0.6090 (2)	0.74137 (6)	0.9366 (2)	0.0323 (4)
C5B	0.5162 (3)	0.64760 (9)	0.9431 (3)	0.0296 (5)
H5B	0.5182	0.6474	1.0592	0.035*
C6B	0.4651 (3)	0.60021 (9)	0.8465 (3)	0.0280 (4)
N61B	0.4173 (3)	0.55420 (9)	0.9144 (3)	0.0372 (5)
H61B	0.411 (4)	0.5555 (12)	1.018 (2)	0.045*
H62B	0.377 (3)	0.5254 (9)	0.855 (3)	0.045*
C1X	−0.1873 (3)	0.25089 (11)	0.5982 (4)	0.0444 (6)
H1X1	−0.3008	0.2544	0.5318	0.067*
H1X2	−0.1902	0.2348	0.7072	0.067*
H1X3	−0.1230	0.2265	0.5401	0.067*
S2X	−0.09248 (7)	0.31824 (3)	0.62631 (8)	0.03668 (17)
O21X	−0.0699 (2)	0.33405 (8)	0.4553 (2)	0.0492 (5)
C3X	0.1057 (3)	0.29648 (12)	0.7398 (3)	0.0446 (6)
H3X1	0.1548	0.2706	0.6716	0.067*
H3X2	0.0937	0.2777	0.8425	0.067*
H3X3	0.1779	0.3291	0.7679	0.067*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0387 (10)	0.0285 (10)	0.0284 (10)	−0.0058 (8)	0.0080 (8)	0.0003 (8)
C2A	0.0346 (11)	0.0302 (11)	0.0259 (11)	−0.0001 (9)	0.0083 (9)	−0.0005 (9)
S21A	0.0509 (4)	0.0380 (3)	0.0250 (3)	−0.0088 (3)	0.0133 (2)	−0.0005 (2)
N3A	0.0381 (10)	0.0301 (10)	0.0230 (9)	−0.0060 (8)	0.0086 (8)	−0.0033 (8)
C4A	0.0393 (12)	0.0330 (12)	0.0239 (11)	−0.0024 (9)	0.0104 (9)	−0.0020 (9)
O41A	0.0614 (11)	0.0412 (10)	0.0270 (9)	−0.0201 (8)	0.0176 (8)	−0.0059 (7)
C5A	0.0392 (11)	0.0344 (12)	0.0222 (10)	−0.0028 (9)	0.0085 (9)	−0.0020 (9)
C6A	0.0351 (11)	0.0331 (12)	0.0272 (11)	0.0007 (9)	0.0065 (9)	−0.0015 (9)
C61A	0.0499 (14)	0.0391 (13)	0.0329 (13)	−0.0097 (11)	0.0066 (11)	−0.0060 (10)
N1B	0.0379 (9)	0.0258 (9)	0.0216 (9)	−0.0013 (7)	0.0078 (7)	−0.0002 (7)
C2B	0.0306 (10)	0.0246 (10)	0.0235 (10)	0.0016 (8)	0.0063 (8)	−0.0005 (8)
N21B	0.0519 (12)	0.0269 (10)	0.0221 (9)	−0.0058 (8)	0.0119 (8)	−0.0009 (8)
N3B	0.0376 (9)	0.0242 (9)	0.0220 (9)	−0.0017 (7)	0.0088 (7)	0.0006 (7)
C4B	0.0303 (10)	0.0280 (11)	0.0222 (10)	0.0028 (8)	0.0065 (8)	−0.0026 (8)
O41B	0.0439 (9)	0.0261 (8)	0.0277 (8)	−0.0027 (6)	0.0095 (7)	−0.0057 (6)
C5B	0.0403 (11)	0.0287 (11)	0.0212 (10)	−0.0004 (9)	0.0098 (9)	0.0003 (9)
C6B	0.0356 (11)	0.0272 (11)	0.0225 (10)	0.0009 (8)	0.0090 (8)	0.0007 (8)
N61B	0.0598 (13)	0.0304 (10)	0.0233 (10)	−0.0099 (9)	0.0132 (9)	−0.0006 (8)
C1X	0.0444 (14)	0.0398 (14)	0.0487 (16)	−0.0043 (11)	0.0090 (12)	0.0095 (12)
S2X	0.0364 (3)	0.0354 (3)	0.0378 (3)	0.0023 (2)	0.0071 (2)	0.0025 (2)
O21X	0.0627 (12)	0.0468 (11)	0.0340 (10)	−0.0190 (9)	0.0013 (8)	0.0081 (8)
C3X	0.0395 (13)	0.0540 (16)	0.0385 (14)	0.0049 (11)	0.0042 (11)	0.0008 (12)

Geometric parameters (Å, º)

N1A—C2A	1.353 (3)	N21B—H22B	0.858 (17)
N1A—C6A	1.370 (3)	N3B—C4B	1.393 (3)
N1A—H1A	0.882 (17)	N3B—H3B	0.902 (17)
C2A—N3A	1.363 (3)	C4B—O41B	1.263 (3)
C2A—S21A	1.668 (2)	C4B—C5B	1.388 (3)
N3A—C4A	1.383 (3)	C5B—C6B	1.397 (3)
N3A—H3A	0.877 (17)	C5B—H5B	0.9500
C4A—O41A	1.238 (3)	C6B—N61B	1.333 (3)
C4A—C5A	1.428 (3)	N61B—H61B	0.864 (18)
C5A—C6A	1.350 (3)	N61B—H62B	0.867 (17)
C5A—H5A	0.9500	C1X—S2X	1.786 (3)
C6A—C61A	1.487 (3)	C1X—H1X1	0.9800
C61A—H61A	0.9800	C1X—H1X2	0.9800
C61A—H62A	0.9800	C1X—H1X3	0.9800
C61A—H63A	0.9800	S2X—O21X	1.5051 (19)
N1B—C2B	1.326 (3)	S2X—C3X	1.776 (3)
N1B—C6B	1.367 (3)	C3X—H3X1	0.9800
C2B—N21B	1.334 (3)	C3X—H3X2	0.9800
C2B—N3B	1.357 (3)	C3X—H3X3	0.9800
N21B—H21B	0.875 (17)
C2A—N1A—C6A	123.9 (2)	C2B—N3B—C4B	122.47 (18)
C2A—N1A—H1A	116.1 (18)	C2B—N3B—H3B	118.3 (17)
C6A—N1A—H1A	119.8 (18)	C4B—N3B—H3B	119.2 (17)
N1A—C2A—N3A	115.4 (2)	O41B—C4B—C5B	127.5 (2)
N1A—C2A—S21A	121.46 (17)	O41B—C4B—N3B	117.33 (19)
N3A—C2A—S21A	123.09 (17)	C5B—C4B—N3B	115.19 (19)
C2A—N3A—C4A	125.14 (19)	C4B—C5B—C6B	119.6 (2)
C2A—N3A—H3A	118.8 (18)	C4B—C5B—H5B	120.2
C4A—N3A—H3A	116.0 (18)	C6B—C5B—H5B	120.2
O41A—C4A—N3A	119.3 (2)	N61B—C6B—N1B	115.56 (19)
O41A—C4A—C5A	124.9 (2)	N61B—C6B—C5B	121.0 (2)
N3A—C4A—C5A	115.8 (2)	N1B—C6B—C5B	123.5 (2)
C6A—C5A—C4A	120.0 (2)	C6B—N61B—H61B	117.9 (19)
C6A—C5A—H5A	120.0	C6B—N61B—H62B	122 (2)
C4A—C5A—H5A	120.0	H61B—N61B—H62B	119 (3)
C5A—C6A—N1A	119.7 (2)	S2X—C1X—H1X1	109.5
C5A—C6A—C61A	124.2 (2)	S2X—C1X—H1X2	109.5
N1A—C6A—C61A	116.0 (2)	H1X1—C1X—H1X2	109.5
C6A—C61A—H61A	109.5	S2X—C1X—H1X3	109.5
C6A—C61A—H62A	109.5	H1X1—C1X—H1X3	109.5
H61A—C61A—H62A	109.5	H1X2—C1X—H1X3	109.5
C6A—C61A—H63A	109.5	O21X—S2X—C3X	106.11 (13)
H61A—C61A—H63A	109.5	O21X—S2X—C1X	104.24 (12)
H62A—C61A—H63A	109.5	C3X—S2X—C1X	97.51 (13)
C2B—N1B—C6B	115.80 (18)	S2X—C3X—H3X1	109.5
N1B—C2B—N21B	119.88 (19)	S2X—C3X—H3X2	109.5
N1B—C2B—N3B	123.45 (19)	H3X1—C3X—H3X2	109.5
N21B—C2B—N3B	116.67 (19)	S2X—C3X—H3X3	109.5
C2B—N21B—H21B	116.6 (19)	H3X1—C3X—H3X3	109.5
C2B—N21B—H22B	115.8 (19)	H3X2—C3X—H3X3	109.5
H21B—N21B—H22B	127 (3)
C6A—N1A—C2A—N3A	−1.9 (3)	C6B—N1B—C2B—N21B	179.03 (19)
C6A—N1A—C2A—S21A	178.73 (17)	C6B—N1B—C2B—N3B	−1.2 (3)
N1A—C2A—N3A—C4A	0.8 (3)	N1B—C2B—N3B—C4B	−0.3 (3)
S21A—C2A—N3A—C4A	−179.87 (18)	N21B—C2B—N3B—C4B	179.50 (19)
C2A—N3A—C4A—O41A	−178.7 (2)	C2B—N3B—C4B—O41B	−178.12 (19)
C2A—N3A—C4A—C5A	1.2 (3)	C2B—N3B—C4B—C5B	1.9 (3)
O41A—C4A—C5A—C6A	177.7 (2)	O41B—C4B—C5B—C6B	178.0 (2)
N3A—C4A—C5A—C6A	−2.3 (3)	N3B—C4B—C5B—C6B	−2.1 (3)
C4A—C5A—C6A—N1A	1.3 (3)	C2B—N1B—C6B—N61B	−178.8 (2)
C4A—C5A—C6A—C61A	−177.4 (2)	C2B—N1B—C6B—C5B	1.0 (3)
C2A—N1A—C6A—C5A	0.9 (3)	C4B—C5B—C6B—N61B	−179.5 (2)
C2A—N1A—C6A—C61A	179.7 (2)	C4B—C5B—C6B—N1B	0.7 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O21X	0.88 (2)	1.89 (2)	2.758 (3)	167 (3)
N3A—H3A···N1B	0.88 (2)	2.26 (2)	3.132 (3)	171 (2)
N21B—H21B···O41A	0.88 (2)	1.97 (2)	2.836 (3)	174 (3)
N21B—H22B···O41B^i	0.86 (2)	2.10 (2)	2.886 (3)	153 (3)
N3B—H3B···O41B^i	0.90 (2)	1.98 (2)	2.807 (2)	153 (2)
N61B—H61B···O41A^ii	0.86 (2)	2.06 (2)	2.916 (3)	171 (3)
N61B—H62B···S21A	0.87 (2)	2.55 (2)	3.386 (2)	162 (3)

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