Pseudopolymorphs of 2,6-diamino­pyrimidin-4-one and 2-amino-6-methyl­pyrimidin-4-one: one or two tautomers present in the same crystal

Gerhardt, V.; Tutughamiarso, M.; Bolte, M.

doi:10.1107/S0108270111013072

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 67| Part 5| May 2011| Pages o179-o187

doi:10.1107/S0108270111013072

Pseudopolymorphs of 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one: one or two tautomers present in the same crystal

Valeska Gerhardt,^a Maya Tutughamiarso ^a and Michael Bolte ^b ^*

^aInstitut für Organische Chemie und Chemische Biologie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany, and ^bInstitut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 6 April 2011; accepted 7 April 2011; online 14 April 2011)

The derivatives of pyrimidin-4-one can adopt either a 1H- or a 3H-tautomeric form, which affects the hydrogen-bonding interactions in cocrystals with compounds containing complementary functional groups. In order to study their tautomeric preferences, we crystallized 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one. During various crystallization attempts, four structures of 2,6-diaminopyrimidin-4-one were obtained, namely solvent-free 2,6-diaminopyrimidin-4-one, C₄H₆N₄O, (I), 2,6-diaminopyrimidin-4-one–dimethylformamide–water (3/4/1), C₄H₆N₄O·1.33C₃H₇NO·0.33H₂O, (Ia), 2,6-diaminopyrimidin-4-one dimethylacetamide monosolvate, C₄H₆N₄O·C₄H₉NO, (Ib), and 2,6-diaminopyrimidin-4-one–N-methylpyrrolidin-2-one (3/2), C₄H₆N₄O·1.5C₅H₉NO, (Ic). The 2,6-diaminopyrimidin-4-one molecules exist only as 3H-tautomers. They form ribbons characterized by R²₂(8) hydrogen-bonding interactions, which are further connected to form three-dimensional networks. An intermolecular N—H⋯N interaction between amine groups is observed only in (I). This might be the reason for the pyramidalization of the amine group. Crystallization experiments on 2-amino-6-methylpyrimidin-4-one yielded two isostructural pseudopolymorphs, namely 2-amino-6-methylpyrimidin-4(3H)-one–2-amino-6-methylpyrimidin-4(1H)-one–dimethylacetamide (1/1/1), C₅H₇N₃O·C₅H₇N₃O·C₄H₉NO, (IIa), and 2-amino-6-methylpyrimidin-4(3H)-one–2-amino-6-methylpyrimidin-4(1H)-one–N-methylpyrrolidin-2-one (1/1/1), C₅H₇N₃O·C₅H₇N₃O·C₅H₉NO, (IIb). In both structures, a 1:1 mixture of 1H- and 3H-tautomers is present, which are linked by three hydrogen bonds similar to a Watson–Crick C–G base pair.

Comment

Pyrimidin-4-one derivatives are of particular interest in pharmacology and molecular biology. They include nucleobases and many important pharmaceutical drugs, e.g. anti-inflammatory (Kawade et al., 2011 ), anticancer (Lu et al., 2007 ), antihistaminic and bronchorelaxant agents (Youssouf et al., 2008 ). Pyrimidin-4-one can exist in three tautomeric forms: as a 1H- or 3H-tautomer or as a hydroxypyrimidine. An NMR study revealed that the preference of each tautomeric form depends on its state, although no hydroxypyrimidine form has ever been observed. In the solid state, only the 3H-tautomer has been found, while in polar solvents, a mixture of 1H-and 3H-tautomers is observed (López et al., 2000 ). These results agree with the two crystal structures containing pyrimidin-4-one in the Cambridge Structural Database (CSD, Version 5.31 of November 2009, plus four updates; Allen, 2002 ), which confirmed that the 3H-tautomer is preferred [CSD refcodes BAGQUV (Vaillancourt et al., 1998 ) and XOLHOW (Bhogala et al., 2008 )].

We are interested in the hydrogen-bonding interaction between pyrimidin-4-one derivatives and compounds containing complementary functional groups. Since the occurrence of tautomers results in different synthon combinations (Bhogala et al., 2008), we crystallized 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one to study their tautomeric preferences. Four structures of 2,6-diaminopyrimidin-4-one were obtained during various crystallization experiments, namely solvent-free 2,6-diaminopyrimidin-4-one, (I), a dimethylformamide–water solvate (3/4/1), (Ia), a dimethylacetamide monosolvate, (Ib), and an N-methylpyrrolidin-2-one (3/2) solvate, (Ic). Another N-methylpyrrolidin-2-one solvate of minor crystal quality was also obtained (Gerhardt et al., 2011 ). All 2,6-diaminopyrimidin-4-one molecules exist as 3H-tautomers. Crystallization attempts on 2-amino-6-methylpyrimidin-4-one yielded two pseudopolymorphs, namely dimethylacetamide monosolvate, (IIa), and N-methylpyrrolidin-2-one monosolvate, (IIb). In both structures, a 1:1 mixture of 1H- and 3H-tautomers is present.

with two N—H⋯N hydrogen bonds (Fig. 2

). This arrangement is similar to that in the cytosine–guanine base pair. The ribbons are rippled and further connected into layers by R₄³(12) interactions. Other N—H⋯O hydrogen bonds stabilize the layers to form a three-dimensional network.

Compound (Ia) formed during crystallization attempts from dimethylformamide (DMF). It crystallizes in the monoclinic space group P2₁ with three planar 2,6-diaminopyrimidin-4-one molecules (r.m.s deviations = 0.008, 0.012 and 0.013 Å for all non-H atoms) and four DMF molecules. Since we used non-water-free solvent, one water molecule is also present in the asymmetric unit (Fig. 3). The three 2,6-diaminopyrimidin-4-one molecules show different hydrogen-bond arrangements. Molecules A and B are connected by either R₂²(8) N—H⋯O or R₂²(8) N—H⋯N bonds to form planar ribbons running parallel to ( $[\overline{1}]$ 01) (Fig. 4). The ribbons are further stabilized by hydrogen bonds to the solvent molecules. One DMF molecule is N—H⋯O hydrogen bonded only to molecule A, while another DMF molecule links molecules A and B by two N—H⋯O hydrogen bonds. Furthermore, chains running along the a axis consisting of N—H⋯O hydrogen-bonded molecules C are observed (Fig. 5). The chain is stabilized by N—H⋯O hydrogen bonds with the participation of solvent molecules. One of the two DMF molecules linked to molecule C is disordered over two sites with a planar arrangement (r.m.s deviation = 0.011 Å). The packing of (Ia) shows ribbons and chains, which are connected by N—H⋯O hydrogen bonds to form a three-dimensional network. The water molecule forms hydrogen bonds bridging the three 2,6-diaminopyrimidin-4-one molecules and thus additionally stabilizes the structure.

The dimethylacetamide (DMAC) monosolvate, (Ib), crystallizes in the monoclinic space group Cc with two 2,6-diaminopyrimidin-4-one (r.m.s deviations = 0.013 and 0.025 Å for all non-H atoms) and two DMAC molecules in the asymmetric unit (Fig. 6). In the packing of (Ib), ribbons consisting of 2,6-diaminopyrimidin-4-one molecules run in two different directions [parallel to ( $[\overline{1}]$ 11) and ( $[\overline{1}]$ $[\overline{1}]$ 1)]. Similar to (Ia), the molecules are stabilized either by N—H⋯O or by N—H⋯N hydrogen bonds with an R₂²(8) pattern (Fig. 7). These ribbons are further N—H⋯O hydrogen bonded to form channels, in which solvent molecules are located (Fig. 8). One DMAC molecule is coplanar with the 2,6-diaminopyrimidin-4-one molecules and shows only van der Waals interactions, while the O atom of the other DMAC molecule is threefold N—H⋯O hydrogen bonded to 2,6-diaminopyrimidin-4-one molecules.

Compound (Ic) crystallizes as an N-methylpyrrolidin-2-one (NMP) solvate with two 2,6-diaminopyrimidin-4-one and three solvent molecules in the asymmetric unit (Fig. 9). The 2,6-diaminopyrimidin-4-one molecules are planar (r.m.s deviations = 0.005 and 0.012 Å for all non-H atoms). R₂²(8) interactions involving either two N—H⋯O or two N—H⋯N hydrogen bonds are again present. Both interactions connect molecules A to form ribbons running parallel to (111), which are additionally stabilized by N—H⋯O bonds between molecule A and one NMP molecule (Fig. 10). In contrast, molecules B form dimers stabilized by R₂²(8) N—H⋯N hydrogen bonds. Two NMP molecules are N—H⋯O hydrogen bonded to each molecule B, and thus inversion-symmetric arrangements of two molecules B and two NMP molecules are formed (Fig. 11). These link the ribbons to form a three-dimensional network.

The two isostructural 2-amino-6-methylpyrimidin-4-one solvates, (IIa) and (IIb), crystallize in the triclinic space group P $[\overline{1}]$ with similar lattice parameters. A 1:1 ratio of 1H- and 3H-tautomers is present in both crystal structures. The asymmetric unit of (IIa) consists of the two tautomers and one DMAC molecule (Fig. 12), while (IIb) crystallizes with the two tautomers and one disordered NMP molecule (Fig. 13). In both structures, the molecules are coplanar with each other, and both the hydrogen-bonding interactions and the crystal packings are similar (Figs. 14 and 15). The two tautomers are linked by two R₂²(8) interactions involving N—H⋯O and N—H⋯N bonds, forming a dimer related to the cytosine–guanine base pair. Two symmetry-equivalent dimers are further connected by two N—H⋯N interactions with an R₂²(8) pattern to give a tetramer. The O atoms of the solvent molecules, either DMAC in (IIa) or NMP in (IIb), adopt identical postions and are R₂¹(6) N—H⋯O hydrogen bonded to the 3H-tautomer. The crystal structures show layers parallel to the (210) plane containing discrete arrangements of the tetramers.

In order to study the preference of the 1H- and 3H-tautomeric forms, a CSD substructure search for pyrimidin-4-one derivatives was undertaken. 15 entries for the 1H form, 39 entries for the 3H form and five entries with both tautomeric forms were found [refcodes ICYTIN (Sharma & McConnell, 1965 ), ICYTIN01 (Portalone & Colapietro, 2007 ), LEJLAN and LEJLOB (Bannister et al., 1994 ), and ZERMIS (Toledo et al., 1995 )]. Examining only entries containing 2,6-diaminopyrimidin-4-one, no 1H-tautomer has been reported [refcodes SEYDIJ (Skoweranda et al., 1990 ) and GIMZUY (Subashini et al., 2007 )]. The preference for the 3H-tautomeric form is also shown in two recently reported polymorphs of the monohydrate (Suleiman Gwaram et al., 2011 ), in the NMP solvate with minor crystal quality (Gerhardt et al., 2011) and in the four crystal structures above, viz. (I) and (Ia)–(Ic). A possible explanation for the absence of the 1H-tautomeric form might be the repulsion of the H atoms from the three amino groups presenting an adjacent donor–donor–donor hydrogen-bonding site. In contrast, 2-amino-6-methylpyrimidin-4-one exists in both 1H- and 3H-tautomeric forms. In the solvent-free P2₁/n structure it exists as a 1H-tautomer (refcode FETSEC; Lowe et al., 1987 ), while in the solvent-free C2/c polymorph, both 1H- and 3H-tautomers are shown as a result of disordered H atoms (refcode ZERMIS; Toledo et al., 1995). The 3H-tautomeric form is observed in its cocrystals with glutaric acid and adipic acid (refcodes ZUKXAE and ZUKXEI; Liao et al., 1996 ). Interestingly, only in the solvates (IIa) and (IIb) do both tautomers exist in a 1:1 ratio.

Almost all 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one molecules are planar. The pyramidalization of one amine group in (I) is also observed in the orthorhombic polymorph of 2,6-diaminopyrimidin-4-one monohydrate [refcode SEYDIJ (Skoweranda et al., 1990), form I according to Suleiman Gwaram et al. (2011)]. Similar to (I), one C—NH₂ bond is longer than the other [1.334 (2) and 1.359 (2) Å], and the sums of the bond angles at the N atoms are 360 and 354°. Different C—NH₂ bond lengths are also observed in the monoclinic polymorph [form III according to Suleiman Gwaram et al. (2011); C—NH₂ = 1.323 (4) and 1.354 (4) Å], but both amine groups are planar [sums of the bond angles at the N atoms = 359 (2) and 356 (2)°, respectively].

Comparing the hydrogen-bond arrangements formed by the 2,6-diaminopyrimidin-4-one molecules, ribbons characterized by R₂²(8) interactions involving either two N—H⋯O or two N—H⋯N bonds are observed in all structures. However, an intermolecular N—H⋯N interaction between the amine groups is only observed in (I) and in the orthorhombic polymorph (form I), which may explain the pyramidalization of one amine group in these two structures. The crystal packings in the various structures show three-dimensional networks additionally stabilized by solvent molecules. The 1H- and 3H-tautomers of 2-amino-6-methylpyrimidin-4-one are linked by three hydrogen bonds, similar to what is observed in the Watson–Crick C–G base pair. Identical arrangements are observed in the five CSD entries for pyrimidin-4-one derivatives containing both tautomeric forms. Altogether, (I) and (Ia)–(Ic) confirm the 3H-tautomer preference of 2,6-diaminopyrimidin-4-one, while there is no preference for 2-amino-6-methylpyrimidin-4-one. It can exist as a 1H- or 3H-tautomer, or as a 1:1 mixture of both tautomers, as shown in the crystal structures of (IIa) and (IIb).

Figure 1
A perspective view of (I)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A partial packing diagram for (I)

. Hydrogen bonds are shown as dashed lines.

Figure 3
A perspective view of (Ia)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds. One of the dimethylformamide molecules (molecule Y) is disordered and only the major occupied site is shown.

Figure 4
A partial packing diagram for (Ia)

. Hydrogen bonds are shown as dashed lines. Only DMF molecules linked to molecules A and B are shown.

Figure 5
A partial packing diagram for (Ia)

. Dashed lines indicate hydrogen bonds. Only DMF molecules linked to molecules C are shown. One of the solvent molecules is disordered and its minor occupied site has been omitted.

Figure 6
A perspective view of (Ib)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.

Figure 7
A partial packing diagram for (Ib)

. Hydrogen bonds are shown as dashed lines. The solvent molecules, which are only stabilized by van der Waals interactions, have been omitted.

Figure 8
A partial packing diagram for (Ib)

. Hydrogen bonds are shown as dashed lines.

Figure 9
A perspective view of (Ic)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.

Figure 10
A partial packing diagram for (Ic)

. Hydrogen bonds are shown as dashed lines. Only molecules A and solvent molecules connected to them are shown.

Figure 11
A partial packing diagram for (Ic)

. Hydrogen bonds are shown as dashed lines. Only molecules B and solvent molecules connected to them are shown.

Figure 12
A perspective view of (IIa)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.

Figure 13
A perspective view of (IIb)

, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds. The solvent molecule is disordered and only the major occupied site is shown.

Figure 14
A partial packing diagram for (IIa)

. Hydrogen bonds are shown as dashed lines.

Figure 15
A partial packing diagram for (IIb)

. Hydrogen bonds are shown as dashed lines. The minor occupied sites of the solvent molecules have been omitted.

Experimental

Solvent evaporation experiments with commercially available 2,6-diaminopyrimidin-4-one under different conditions yielded (I) and (Ia)–(Ic) (Table 7). Single crystals of (IIa) and (IIb) were obtained by crystallization of commercially available 2-amino-6-methylpyrimidin-4-one (Table 8). None of the solvents used in the experiments was water-free.

Compound (I)

Crystal data

C₄H₆N₄O
M_r = 126.13
Monoclinic, P 2₁ /c
a = 7.7150 (9) Å
b = 9.7229 (7) Å
c = 7.4514 (8) Å
β = 114.453 (8)°
V = 508.81 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 173 K
0.45 × 0.35 × 0.30 mm

Data collection

Stoe IPDS II two-circle diffractometer
7117 measured reflections
953 independent reflections
737 reflections with I > 2σ(I)
R_int = 0.128

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.092
S = 0.97
953 reflections
103 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21—H21A⋯O41ⁱ	0.90 (2)	1.98 (2)	2.8678 (17)	165.9 (19)
N21—H21B⋯N61ⁱⁱ	0.89 (2)	2.34 (2)	3.1304 (19)	147.9 (18)
N3—H3⋯N1ⁱⁱ	0.92 (2)	2.15 (2)	3.0370 (17)	163.2 (17)
N61—H61B⋯N1ⁱⁱⁱ	0.89 (2)	2.34 (2)	3.2131 (18)	166.8 (16)
N61—H61A⋯O41^iv	0.89 (2)	2.05 (2)	2.9296 (18)	172.5 (17)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) -x+1, -y+1, -z+1; (iv) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Compound (Ia)

Crystal data

C₄H₆N₄O·4/3C₃H₇NO·1/3H₂O
M_r = 229.59
Monoclinic, P 2₁
a = 7.4417 (6) Å
b = 25.3217 (18) Å
c = 9.8578 (7) Å
β = 108.476 (6)°
V = 1761.8 (2) Å³
Z = 6
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.50 × 0.30 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer
28505 measured reflections
3380 independent reflections
2636 reflections with I > 2σ(I)
R_int = 0.170

Refinement

R[F² > 2σ(F²)] = 0.040
wR(F²) = 0.085
S = 0.91
3380 reflections
459 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 2
Hydrogen-bond geometry (Å, °) for (Ia)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21A—H21A⋯N1Bⁱ	0.88	2.11	2.985 (4)	170
N21A—H21B⋯O1Xⁱ	0.88	2.12	2.820 (4)	136
N3A—H3A⋯O41B	0.88	1.86	2.734 (3)	175
N61A—H61B⋯O1W	0.88	2.05	2.872 (4)	155
N21B—H21C⋯N1Aⁱⁱ	0.88	2.05	2.931 (4)	175
N21B—H21D⋯O1V	0.88	2.07	2.920 (4)	161
N3B—H3B⋯O41A	0.88	1.95	2.812 (3)	167
N61B—H61C⋯O1X	0.88	2.16	3.028 (4)	168
N61B—H61D⋯O41C	0.88	2.02	2.886 (4)	169
N21C—H21E⋯O41Aⁱⁱⁱ	0.88	2.11	2.945 (4)	158
N21C—H21F⋯O1Z	0.88	2.10	2.874 (4)	146
N3C—H3C⋯O1V^iv	0.88	2.03	2.890 (3)	166
N61C—H61E⋯O41C^v	0.88	1.97	2.744 (3)	147
N61C—H61F⋯O1Y	0.88	2.07	2.949 (4)	173
O1V—H1V⋯N1C^vi	0.84 (1)	2.06 (2)	2.856 (3)	157 (3)
O1V—H2V⋯O41A	0.84 (1)	1.96 (2)	2.751 (3)	156 (4)
Symmetry codes: (i) x+1, y, z+1; (ii) x-1, y, z-1; (iii) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (iv) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (v) x+1, y, z; (vi) $[-x+1, y-{\script{1\over 2}}, -z+1]$ .

Compound (Ib)

Crystal data

C₄H₆N₄O·C₄H₉NO
M_r = 213.25
Monoclinic, C c
a = 19.1494 (13) Å
b = 7.8704 (4) Å
c = 14.9104 (11) Å
β = 104.868 (6)°
V = 2172.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.50 × 0.35 × 0.30 mm

Data collection

Stoe IPDS II two-circle diffractometer
12494 measured reflections
2054 independent reflections
1922 reflections with I > 2σ(I)
R_int = 0.096

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.126
S = 1.04
2054 reflections
277 parameters
22 restraints
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 3
Hydrogen-bond geometry (Å, °) for (Ib)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21A—H21A⋯N1B	0.88	2.07	2.946 (4)	171
N21A—H21B⋯O2X	0.88	2.46	3.176 (4)	139
N3A—H3A⋯O41Bⁱ	0.88	1.89	2.765 (3)	174
N61A—H61A⋯O2Xⁱⁱ	0.88	2.15	2.939 (4)	150
N61A—H61B⋯O41Bⁱⁱⁱ	0.88	2.22	2.975 (4)	144
N21B—H21C⋯N1A	0.88	2.16	3.029 (4)	172
N3B—H3B⋯O41A^iv	0.88	1.84	2.700 (4)	166
N61B—H61C⋯O2X	0.88	2.17	2.960 (4)	149
N61B—H61D⋯O41A^v	0.88	1.95	2.813 (4)	165
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (v) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Compound (Ic)

Crystal data

C₄H₆N₄O·3/2C₅H₉NO
M_r = 274.83
Triclinic, $[P \overline 1]$
a = 8.4550 (9) Å
b = 10.0803 (9) Å
c = 17.0735 (15) Å
α = 75.558 (7)°
β = 78.222 (8)°
γ = 81.363 (8)°
V = 1371.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.25 × 0.20 × 0.20 mm

Data collection

Stoe IPDS II two-circle diffractometer
18821 measured reflections
5116 independent reflections
2940 reflections with I > 2σ(I)
R_int = 0.091

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.127
S = 0.91
5116 reflections
355 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 4
Hydrogen-bond geometry (Å, °) for (Ic)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21A—H21A⋯O2Xⁱ	0.88	2.22	3.092 (3)	169
N21A—H21B⋯O41B	0.88	2.00	2.756 (3)	143
N3A—H3A⋯O41Aⁱⁱ	0.88	1.87	2.750 (3)	177
N61A—H61A⋯N1Aⁱ	0.88	2.15	3.023 (3)	169
N61A—H61B⋯O2X	0.88	2.14	2.891 (3)	142
N21B—H21C⋯O2Zⁱⁱⁱ	0.88	2.12	2.989 (3)	170
N21B—H21D⋯O2Y	0.88	2.06	2.832 (3)	146
N3B—H3B⋯O2Y	0.88	2.15	2.904 (3)	143
N61B—H61C⋯N1Bⁱⁱⁱ	0.88	2.13	3.001 (3)	170
N61B—H61D⋯O2Z	0.88	2.11	2.840 (3)	139
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) -x+2, -y+1, -z.

Compound (IIa)

Crystal data

C₅H₇N₃O·C₅H₇N₃O·C₄H₉NO
M_r = 337.39
Triclinic, $[P \overline 1]$
a = 7.8763 (13) Å
b = 9.6078 (17) Å
c = 12.3115 (19) Å
α = 108.780 (13)°
β = 95.194 (13)°
γ = 99.959 (13)°
V = 858.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.40 × 0.25 × 0.10 mm

Data collection

Stoe IPDS II two-circle diffractometer
7199 measured reflections
3208 independent reflections
1427 reflections with I > 2σ(I)
R_int = 0.131

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.204
S = 0.82
3208 reflections
223 parameters
H-atom parameters constrained
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 5
Hydrogen-bond geometry (Å, °) for (IIa)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21A—H21A⋯O41B	0.88	1.92	2.803 (4)	178
N21A—H21B⋯O2X	0.88	2.06	2.843 (4)	147
N1A—H1A⋯O2X	0.88	2.02	2.807 (4)	149
N3B—H3B⋯N3A	0.88	1.97	2.844 (4)	177
N21B—H21C⋯N1Bⁱ	0.88	2.10	2.969 (4)	172
N21B—H21D⋯O41A	0.88	2.00	2.877 (4)	173
Symmetry code: (i) -x+1, -y, -z.

Compound (IIb)

Crystal data

C₅H₇N₃O·C₅H₇N₃O·C₅H₉NO
M_r = 349.40
Triclinic, $[P \overline 1]$
a = 7.3321 (7) Å
b = 9.8805 (9) Å
c = 12.5860 (12) Å
α = 102.835 (7)°
β = 98.830 (8)°
γ = 91.555 (8)°
V = 876.70 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 173 K
0.45 × 0.35 × 0.25 mm

Data collection

Stoe IPDS II two-circle diffractometer
13229 measured reflections
3267 independent reflections
1883 reflections with I > 2σ(I)
R_int = 0.149

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.176
S = 0.82
3267 reflections
242 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.34 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 6
Hydrogen-bond geometry (Å, °) for (IIb)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1A—H1A⋯O2X	0.88	2.00	2.800 (3)	151
N21A—H21A⋯O41B	0.88	1.92	2.794 (3)	173
N21A—H21B⋯O2X	0.88	2.09	2.869 (3)	146
N3B—H3B⋯N3A	0.88	1.97	2.838 (3)	171
N21B—H21D⋯O41A	0.88	2.01	2.888 (3)	179
N21B—H21C⋯N1Bⁱ	0.88	2.09	2.962 (3)	172
Symmetry code: (i) -x+1, -y+2, -z+2.

Table 7
Crystallization of 2,6-diaminopyrimidin-4-one

Crystal	2,6-Diaminopyrimidin-4-one (mg, mmol)	Solvent	Temperature
(I)	4.2, 0.033	Methanol (500 µl)	323 K
(Ia)	1.9, 0.015	DMF (100 µl)	Room temperature
(Ib)	2.1, 0.017	DMAC (200 µl)	323 K
(Ic)	3.0, 0.024	NMP (50 µl)	Room temperature

Table 8
Crystallization of 2-amino-6-methylpyrimidin-4-one

Crystal	2-Amino-6-methylpyrimidin-4-one (mg, mmol)	Solvent	Temperature
(IIa)	2.3, 0.018	DMAC (150 µl)	277 K
(IIb)	1.9, 0.015	NMP (50 µl)	323 K

The H atoms, except those bonded to disordered solvent atoms and to solvent water, were initially located by difference Fourier synthesis. Subsequently, 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 or 1.2U_eq(C) for secondary and aromatic H atoms. In (I), H atoms bonded to N atoms were refined isotropically, while in the other structures, they were refined using a riding model, with amide and terminal N—H = 0.88 Å and with U_iso(H) = 1.2U_eq(N). For the water molecule in (Ia), the following restraints were applied during refinement: O—H = 0.84 (1) Å and H⋯H = 1.40 (1) Å, with U_iso(H) = 1.2U_eq(O). Similarity restraints were applied for the 1,2 and 1,3 distances of both DMAC molecules in (Ib), and for the minor occupied orientation of the NMP molecule in (IIb).

In (Ia), all C atoms of one DMF molecule are disordered over two positions, with a site-occupation factor of 0.67 (1) for the major occupied orientation. In (IIb), the NMP molecule is disordered over a pseudo-mirror plane along atoms O2X and C5Y. The site-occupation factor for the major occupied orientation is 0.78 (1). The disordered atoms in (Ia) and (IIb) were refined isotropically.

The E-value distribution of (Ib) could not be used as a hint for or against a centrosymmetric space group (mean value of |E² − 1| = 0.874). A refinement attempt for (Ib) in the centrosymmetric space group C2/c showed difference electron densities higher than 0.50 e Å⁻³ within the nonsolvent molecule, and both solvent molecules are highly disordered. In spite of a possible higher symmetry, tested by ADDSYM (Le Page, 1987 , 1988 ; Spek, 2009 ), (Ib) was refined in the noncentrosymmetric space group Cc, which led to ordered solvent molecules. For (Ia) and (Ib), Friedel pairs were merged prior to refinement, due to the absence of anomalous scatterers. The absolute structure was arbitrarily assigned.

For all compounds, data collection: X-AREA (Stoe & Cie, 2001 ); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Version 2.2; Macrae et al., 2008 ) and XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, Ia, Ib, Ic, IIa, IIb, global. DOI: 10.1107/S0108270111013072/sk3407sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270111013072/sk3407Isup2.hkl

Structure factors: contains datablock Ia. DOI: 10.1107/S0108270111013072/sk3407Iasup3.hkl

Structure factors: contains datablock Ib. DOI: 10.1107/S0108270111013072/sk3407Ibsup4.hkl

Structure factors: contains datablock Ic. DOI: 10.1107/S0108270111013072/sk3407Icsup5.hkl

Structure factors: contains datablock IIa. DOI: 10.1107/S0108270111013072/sk3407IIasup6.hkl

Structure factors: contains datablock IIb. DOI: 10.1107/S0108270111013072/sk3407IIbsup7.hkl

Comment top

Pyrimidin-4-one derivatives are of particular interest in pharmacology and molecular biology. They include nucleobases and many important pharmaceutical drugs, e.g. anti-inflammatory (Kawade et al., 2011), anticancer (Lu et al., 2007), antihistaminic and bronchorelaxant agents (Youssouf et al., 2008). Pyrimidin-4-one can exist in three tautomeric forms: a (1H) or a (3H) tautomer or as a hydroxypyrimidine. An NMR study revealed that the preference of each tautomeric form depends on its state, although no hydroxypyrimidine form has ever been observed. In the solid state, only the (3H) tautomer has been found, while in polar solvents, a mixture of (1H) and (3H) tautomers is observed (López et al., 2000). These results agree with the two crystal structures containing pyrimidin-4-one in the Cambridge Structural Database (CSD, Version 5.31 of November 2009, plus four updates; Allen, 2002), which confirmed that the (3H) tautomer is preferred [CSD refcodes BAGQUV (Vaillancourt et al., 1998) and XOLHOW (Bhogala et al., 2008)].

We are interested in the hydrogen-bonding interaction between pyrimidin-4-one derivatives and compounds containing complementary functional groups. Since the occurrence of tautomers results in different synthon combinations (Bhogala et al., 2008), we crystallized 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one to study their tautomeric preferences. Four structures of 2,6-diaminopyrimidin-4-one were obtained during various crystallization experiments, namely solvent-free 2,6-diaminopyrimidin-4-one, (I), a dimethylformamide–water solvate (3/4/1), (Ia), a dimethylacetamide monosolvate, (Ib), and an N-methyl-2-pyrrolidone (3/2) solvate, (Ic). Another N-methyl-2-pyrrolidone solvate of minor crystal quality was also obtained (Gerhardt et al., 2011). All 2,6-diaminopyrimidin-4-one molecules exist as (3H) tautomers. Crystallization attempts on 2-amino-6-methylpyrimidin-4-one yielded two pseudopolymorphs, namely dimethylacetamide monosolvate, (IIa), and N-methyl-2-pyrrolidone monosolvate, (IIb). In both structures, a 1:1 mixture of (1H) and (3H) tautomers is present.

2,6-Diaminopyrimidin-4-one, (I), crystallizes in the monoclinic space group P2₁/c with one molecule in the asymmetric unit (Fig. 1). One amine group is planar and twisted slightly out of the plane of the ring, while the other is pyramidalized and shows a longer C—NH₂ bond than the planar one [sums of the C—N—H and H—N—H angles at the N atoms = 359.1 (N21) and 347.3° (N61); C—NH₂ = 1.337 (2) (N21) and 1.365 (2) Å (N61)]. The 2,6-diaminopyrimidin-4-one molecules form ribbons characterized by three hydrogen bonds, consisting of one R²₂(8) interaction (Bernstein et al., 1995) with N—H···O and N—H···N hydrogen bonds, and another R²₂(8) interaction with two N—H···N hydrogen bonds (Fig. 2). This arrangement is similar to that in the cytosine–guanine base pair. The ribbons are rippled and further connected into layers by R³₄(12) interactions. Other N—H···O hydrogen bonds stabilize the layers to form a three-dimensional network.

Compound (Ia) formed during crystallization attempts from dimethylformamide (DMF). It crystallizes in the monoclinic space group P2₁ with three planar 2,6-diaminopyrimidin-4-one molecules (r.m.s deviations = 0.008, 0.012 and 0.013 Å for all non-H atoms) and four DMF molecules. Since we used non-water-free solvent, one water molecule is also present in the asymmetric unit (Fig. 3). The three 2,6-diaminopyrimidin-4-one molecules show different hydrogen-bond arrangements. Molecules A and B are connected by either R²₂(8) N—H···O or R²₂(8) N—H···N bonds to form planar ribbons running parallel to (101) (Fig. 4). The ribbons are further stabilized by hydrogen bonds to the solvent molecules. One DMF molecule is N—H···O hydrogen-bonded only to molecule A, while another DMF molecule links molecules A and B by two N—H···O hydrogen bonds. Furthermore, chains running along the a axis consisting of N—H···O hydrogen-bonded molecules C are observed (Fig. 5). The chain is stabilized by N—H···O hydrogen bonds with the participation of solvent molecules. One of the two DMF molecules linked to molecule C is disordered over two sites with a planar arrangement (r.m.s deviation = 0.011 Å). The packing of (Ia) shows ribbons and chains, which are connected by N—H···O hydrogen bonds to form a three-dimensional network. The water molecule forms hydrogen bonds bridging the three 2,6-diaminopyrimidin-4-one molecules and thus additionally stabilizes the structure.

The dimethylacetamide (DMAC) monosolvate, (Ib), crystallizes in the monoclinic space group Cc with two 2,6-diaminopyrimidin-4-one (r.m.s deviations 0.013 and 0.025 Å for all non-H atoms) and two DMAC molecules in the asymmetric unit (Fig. 6). In the packing of (Ib), ribbons consisting of 2,6-diaminopyrimidin-4-one molecules run in two different directions [parallel to (111) and (111)]. Similar to (Ia), the molecules are stabilized either by N—H···O or by N—H···N hydrogen bonds with an R²₂(8) pattern (Fig. 7). These ribbons are further N—H···O hydrogen-bonded to form channels, in which solvent molecules are located (Fig. 8). One DMAC molecule is coplanar with the 2,6-diaminopyrimidin-4-one molecules and shows only van der Waals interactions, while the O atom of the other DMAC molecule is threefold N—H···O hydrogen-bonded to 2,6-diaminopyrimidin-4-one molecules.

Compound (Ic) crystallizes as an N-methyl-2-pyrrolidinone (NMP) solvate with two 2,6-diaminopyrimidin-4-one and three solvent molecules in the asymmetric unit (Fig. 9). The 2,6-diaminopyrimidin-4-one molecules are planar (r.m.s deviations 0.005 and 0.012 Å for all non-H atoms). R²₂(8) interactions involving either two N—H···O or two N—H···N hydrogen bonds are again present. Both interactions connect molecules A to form ribbons running parallel to (111), which are additionally stabilized by N—H···O bonds between molecule A and one NMP molecule (Fig. 10). In contrast, molecules B form dimers stabilized by R²₂(8) N—H···N hydrogen bonds. Two NMP molecules are N—H···O hydrogen-bonded to each molecule B, thus inversion-symmetric arrangements of two molecules B and two NMP molecules are formed (Fig. 11). These link the ribbons to form a three-dimensional network.

The two isostructural 2-amino-6-methylpyrimidin-4-one solvates, (IIa) and (IIb), crystallize in the triclinic space group P1 with similar lattice parameters. A 1:1 ratio of (1H) and (3H) tautomers is present in both crystals. The asymmetric unit of (IIa) consists of the two tautomers and one disordered DMAC molecule (Fig. 12), while (IIb) crystallizes with the two tautomers and one NMP molecule (Fig. 13). In both structures, the molecules are coplanar with each other, and both the hydrogen-bonding interactions and the crystal packings are similar (Figs. 14 and 15). The two tautomers are linked by two R²₂(8) interactions involving N—H···O and N—H···N bonds, forming a dimer related to the cytosine–guanine base pair. Two symmetry-equivalent dimers are further connected by two N—H···N interactions with an R²₂(8) pattern to give a tetramer. The O atoms of the solvent molecules, either DMAC in (IIa) or NMP in (IIb), adopt identical postions and are R¹₂(6) N—H···O hydrogen-bonded to the (3H) tautomer. The crystal structures show layers parallel to the (210) plane containing discrete arrangements of the tetramers.

In order to study the preference of the (1H) and (3H) tautomeric forms, a CSD substructure search for pyrimidin-4-one derivatives was undertaken. 15 entries for the (1H), 39 entries for the (3H) and five entries with both tautomeric forms were found [refcodes ICYTIN (Sharma & McConnell, 1965), ICYTIN01 (Portalone & Colapietro, 2007), LEJLAN and LEJLOB (Bannister et al., 1994), and ZERMIS (Toledo et al., 1995)]. Examining only entries containing 2,6-diaminopyrimidin-4-one, no (1H) tautomer has been reported [refcodes SEYDIJ (Skoweranda et al., 1990) and GIMZUY (Subashini et al., 2007)]. The preference for the (3H) tautomeric form is also shown in two recently reported polymorphs of the monohydrate (Suleiman Gwaram et al., 2011), in the NMP solvate with minor crystal quality (Gerhardt et al., 2011) and in the four crystal structures above, (I) and (Ia)–(Ic). A possible explanation for the absence of the (1H) tautomeric form might be the repulsion of the H atoms from the three amino groups presenting an adjacent donor–donor–donor hydrogen-bonding site. In contrast, 2-amino-6-methylpyrimidin-4-one exists in both (1H) and (3H) tautomeric forms. In the solvent-free P2₁/n structure it exists as a (1H) tautomer [refcode FETSEC (Lowe et al., 1987)], while in the solvent-free C2/c polymorph, both (1H) and (3H) tautomers are shown as a result of disordered H atoms [refcode ZERMIS (Toledo et al., 1995)]. The (3H) tautomeric form is observed in its cocrystals with glutaric acid and adipic acid [refcodes ZUKXAE and ZUKXEI (Liao et al., 1996)]. Interestingly, only in the solvates (IIa) and (IIb) do both tautomers exist in a 1:1 ratio.

Almost all 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one molecules are planar. The pyramidalization of one amine group in (I) is also observed in the orthorhombic polymorph of 2,6-diaminopyrimidin-4-one monohydrate [refcode SEYDIJ (Skoweranda et al., 1990), form I according to Suleiman Gwaram et al., 2011]. Similar to (I), one C—NH₂ bond is longer than the other [1.334 (2) and 1.359 (2) Å], and the sums of the bond angles at the N atoms are 360 and 354°. Different C—NH₂ bond lengths are also observed in the monoclinic polymorph [form III according to Suleiman Gwaram et al., 2011; C—NH₂ = 1.323 (4) and 1.354 (4) Å], but both amine groups are planar [sums of the bond angles at the N atoms = 359 (2) and 356 (2)°, respectively].

Comparing the hydrogen-bond arrangements formed by the 2,6-diaminopyrimidin-4-one molecules, ribbons characterized by R²₂(8) interactions involving either two N—H···O or two N—H···N bonds are observed in all structures. However, an intermolecular N—H···N interaction between the amine groups is only observed in (I) and in the orthorhombic polymorph (form I), which may explain the pyramidalization of one amine group in these two structures. The crystal packings in the various structures show three-dimensional networks additionally stabilized by solvent molecules. The (1H) and (3H) tautomers of 2-amino-6-methylpyrimidin-4-one are linked by three hydrogen bonds, similar to what is observed in the Watson–Crick C–G base pair. Identical arrangements are observed in the five CSD entries for pyrimidin-4-one derivatives containing both tautomeric forms. Altogether, (I) and (Ia)–(Ic) confirm the (3H) tautomer preference of 2,6-diaminopyrimidin-4-one, while there is no preference for 2-amino-6-methylpyrimidin-4-one. It can exist as a (1H), a (3H) or a 1:1 mixture of both tautomers, as shown in the crystal structures of (IIa) and (IIb).

Related literature top

For related literature, see: Allen (2002); Bannister et al. (1994); Bernstein et al. (1995); Bhogala et al. (2008); Gerhardt et al. (2011); Kawade et al. (2011); López et al. (2000); Le Page (1987, 1988); Liao et al. (1996); Lowe et al. (1987); Lu et al. (2007); Portalone & Colapietro (2007); Sharma & McConnell (1965); Skoweranda et al. (1990); Spek (2009); Subashini et al. (2007); Suleiman Gwaram, Khaledi, Mohd Ali & Olmstead (2011); Toledo et al. (1995); Vaillancourt et al. (1998); Youssouf et al. (2008).

Experimental top

Computing details top

For all compounds, data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Version 2.2; Macrae et al., 2008) and XP (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. A perspective view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial packing diagram for (I). Hydrogen bonds are shown as dashed lines.
	Fig. 3. A perspective view of (Ia), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds. One of the dimethylformamide molecules (molecule Y) is disordered; only the major occupied site is shown.
	Fig. 4. A partial packing diagram for (Ia). Hydrogen bonds are shown as dashed lines. Only DMF molecules linked to molecules A and B are shown.
	Fig. 5. A partial packing diagram for (Ia). Dashed lines indicate hydrogen bonds. Only DMF molecules linked to molecules C are shown. One of the solvent molecules is disordered and its minor occupied site has been omitted.
	Fig. 6. A perspective view of (Ib), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 7. A partial packing diagram for (Ib). Hydrogen bonds are shown as dashed lines. The solvent molecules, which are only stabilized by van der Waals interactions, have been omitted.
	Fig. 8. A partial packing diagram for (Ib). Hydrogen bonds are shown as dashed lines.
	Fig. 9. A perspective view of (Ic), 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 (Ic). Hydrogen bonds are shown as dashed lines. Only molecules A and solvent molecules connected to them are shown.
	Fig. 11. A partial packing diagram for (Ic). Hydrogen bonds are shown as dashed lines. Only molecules B and solvent molecules connected to them are shown.
	Fig. 12. A perspective view of (IIa), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds.
	Fig. 13. A perspective view of (IIb), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Dashed lines indicate hydrogen bonds. The solvent molecule is disordered and only the major occupied site is shown.
	Fig. 14. A partial packing diagram for (IIa). Hydrogen bonds are shown as dashed lines.
	Fig. 15. A partial packing diagram for (IIb). Hydrogen bonds are shown as dashed lines. The minor occupied sites of the solvent molecules have been omitted.

(I) 2,6-diaminopyrimidin-4-one top

Crystal data top

C₄H₆N₄O	F(000) = 264
M_r = 126.13	D_x = 1.647 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3967 reflections
a = 7.7150 (9) Å	θ = 3.6–25.9°
b = 9.7229 (7) Å	µ = 0.13 mm⁻¹
c = 7.4514 (8) Å	T = 173 K
β = 114.453 (8)°	Plate, colourless
V = 508.81 (9) Å³	0.45 × 0.35 × 0.30 mm
Z = 4

Data collection top

Stoe IPDS II two-circle diffractometer	737 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.128
Graphite monochromator	θ_max = 25.6°, θ_min = 3.6°
ω scans	h = −9→9
7117 measured reflections	k = −11→10
953 independent reflections	l = −9→9

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.092	w = 1/[σ²(F_o²) + (0.0533P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max < 0.001
953 reflections	Δρ_max = 0.19 e Å⁻³
103 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.050 (9)

Crystal data top

C₄H₆N₄O	V = 508.81 (9) Å³
M_r = 126.13	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7150 (9) Å	µ = 0.13 mm⁻¹
b = 9.7229 (7) Å	T = 173 K
c = 7.4514 (8) Å	0.45 × 0.35 × 0.30 mm
β = 114.453 (8)°

Data collection top

Stoe IPDS II two-circle diffractometer	737 reflections with I > 2σ(I)
7117 measured reflections	R_int = 0.128
953 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.092	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.19 e Å⁻³
953 reflections	Δρ_min = −0.29 e Å⁻³
103 parameters

Special details top

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

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

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

	x	y	z	U_iso*/U_eq
N1	0.44747 (17)	0.35695 (12)	0.61684 (17)	0.0152 (3)
C2	0.5269 (2)	0.23804 (14)	0.6958 (2)	0.0142 (3)
N21	0.7024 (2)	0.23796 (14)	0.8406 (2)	0.0185 (3)
H21A	0.747 (3)	0.320 (2)	0.897 (3)	0.037 (5)*
H21B	0.761 (3)	0.159 (2)	0.890 (3)	0.036 (5)*
N3	0.43741 (18)	0.11555 (13)	0.63261 (17)	0.0154 (3)
H3	0.490 (3)	0.036 (2)	0.698 (3)	0.035 (5)*
C4	0.2545 (2)	0.10530 (15)	0.4819 (2)	0.0149 (4)
O41	0.18451 (15)	−0.01289 (11)	0.43465 (15)	0.0208 (3)
C5	0.1700 (2)	0.23046 (14)	0.3980 (2)	0.0155 (4)
H5	0.0455	0.2321	0.2948	0.019*
C6	0.2692 (2)	0.35141 (14)	0.4666 (2)	0.0144 (4)
N61	0.1955 (2)	0.47663 (13)	0.38987 (19)	0.0176 (4)
H61B	0.286 (3)	0.535 (2)	0.393 (3)	0.029 (5)*
H61A	0.084 (3)	0.4742 (18)	0.286 (3)	0.023 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0150 (7)	0.0127 (6)	0.0150 (6)	0.0001 (5)	0.0033 (5)	0.0014 (5)
C2	0.0147 (7)	0.0141 (7)	0.0141 (7)	−0.0020 (5)	0.0065 (6)	−0.0010 (5)
N21	0.0151 (7)	0.0135 (7)	0.0197 (7)	−0.0001 (5)	0.0000 (5)	0.0002 (5)
N3	0.0154 (7)	0.0106 (6)	0.0168 (7)	0.0005 (5)	0.0034 (5)	0.0018 (5)
C4	0.0145 (8)	0.0156 (7)	0.0139 (7)	−0.0022 (6)	0.0050 (6)	−0.0014 (6)
O41	0.0194 (6)	0.0128 (6)	0.0225 (6)	−0.0018 (4)	0.0010 (4)	−0.0013 (4)
C5	0.0132 (7)	0.0156 (8)	0.0144 (7)	−0.0013 (5)	0.0024 (6)	−0.0006 (5)
C6	0.0158 (7)	0.0152 (7)	0.0135 (7)	0.0016 (6)	0.0073 (6)	0.0008 (6)
N61	0.0162 (7)	0.0129 (7)	0.0178 (7)	0.0003 (5)	0.0013 (6)	0.0012 (5)

Geometric parameters (Å, º) top

N1—C2	1.3266 (18)	C4—O41	1.2565 (18)
N1—C6	1.369 (2)	C4—C5	1.400 (2)
C2—N21	1.337 (2)	C5—C6	1.381 (2)
C2—N3	1.3592 (18)	C5—H5	0.9500
N21—H21A	0.90 (2)	C6—N61	1.3651 (18)
N21—H21B	0.89 (2)	N61—H61B	0.89 (2)
N3—C4	1.396 (2)	N61—H61A	0.89 (2)
N3—H3	0.92 (2)

C2—N1—C6	116.85 (12)	O41—C4—C5	127.08 (13)
N1—C2—N21	119.07 (13)	N3—C4—C5	115.22 (13)
N1—C2—N3	122.34 (14)	C6—C5—C4	119.38 (14)
N21—C2—N3	118.58 (13)	C6—C5—H5	120.3
C2—N21—H21A	116.1 (13)	C4—C5—H5	120.3
C2—N21—H21B	120.4 (13)	N61—C6—N1	114.26 (13)
H21A—N21—H21B	122.6 (19)	N61—C6—C5	122.25 (14)
C2—N3—C4	122.71 (13)	N1—C6—C5	123.49 (13)
C2—N3—H3	120.4 (12)	C6—N61—H61B	111.7 (12)
C4—N3—H3	116.5 (12)	C6—N61—H61A	115.3 (12)
O41—C4—N3	117.70 (13)	H61B—N61—H61A	120.3 (17)

C6—N1—C2—N21	178.82 (13)	O41—C4—C5—C6	−179.04 (13)
C6—N1—C2—N3	−0.1 (2)	N3—C4—C5—C6	0.14 (19)
N1—C2—N3—C4	−0.8 (2)	C2—N1—C6—N61	−179.36 (12)
N21—C2—N3—C4	−179.79 (13)	C2—N1—C6—C5	1.1 (2)
C2—N3—C4—O41	−179.95 (12)	C4—C5—C6—N61	179.39 (13)
C2—N3—C4—C5	0.8 (2)	C4—C5—C6—N1	−1.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21A···O41ⁱ	0.90 (2)	1.98 (2)	2.8678 (17)	165.9 (19)
N21—H21B···N61ⁱⁱ	0.89 (2)	2.34 (2)	3.1304 (19)	147.9 (18)
N3—H3···N1ⁱⁱ	0.92 (2)	2.15 (2)	3.0370 (17)	163.2 (17)
N61—H61B···N1ⁱⁱⁱ	0.89 (2)	2.34 (2)	3.2131 (18)	166.8 (16)
N61—H61A···O41^iv	0.89 (2)	2.05 (2)	2.9296 (18)	172.5 (17)

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

(Ia) 2,6-diaminopyrimidin-4-one dimethylformamide solvate hydrate (3/4/1) top

Crystal data top

C₄H₆N₄O·4/3C₃H₇NO·1/3H₂O	F(000) = 736
M_r = 229.59	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 12963 reflections
a = 7.4417 (6) Å	θ = 3.3–25.8°
b = 25.3217 (18) Å	µ = 0.10 mm⁻¹
c = 9.8578 (7) Å	T = 173 K
β = 108.476 (6)°	Block, colourless
V = 1761.8 (2) Å³	0.50 × 0.30 × 0.20 mm
Z = 6

Data collection top

Stoe IPDS II two-circle diffractometer	2636 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.170
Graphite monochromator	θ_max = 25.7°, θ_min = 3.3°
ω scans	h = −9→9
28505 measured reflections	k = −30→30
3380 independent reflections	l = −11→11

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.085	w = 1/[σ²(F_o²) + (0.0331P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
3380 reflections	Δρ_max = 0.19 e Å⁻³
459 parameters	Δρ_min = −0.19 e Å⁻³
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0121 (15)

Crystal data top

C₄H₆N₄O·4/3C₃H₇NO·1/3H₂O	V = 1761.8 (2) Å³
M_r = 229.59	Z = 6
Monoclinic, P2₁	Mo Kα radiation
a = 7.4417 (6) Å	µ = 0.10 mm⁻¹
b = 25.3217 (18) Å	T = 173 K
c = 9.8578 (7) Å	0.50 × 0.30 × 0.20 mm
β = 108.476 (6)°

Data collection top

Stoe IPDS II two-circle diffractometer	2636 reflections with I > 2σ(I)
28505 measured reflections	R_int = 0.170
3380 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	4 restraints
wR(F²) = 0.085	H atoms treated by a mixture of independent and constrained refinement
S = 0.91	Δρ_max = 0.19 e Å⁻³
3380 reflections	Δρ_min = −0.19 e Å⁻³
459 parameters

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.8108 (4)	0.30056 (11)	1.2152 (3)	0.0259 (6)
C2A	0.7168 (5)	0.34081 (12)	1.1395 (3)	0.0230 (7)
N21A	0.7359 (4)	0.38915 (11)	1.1972 (3)	0.0309 (7)
H21A	0.8108	0.3941	1.2854	0.037*
H21B	0.6735	0.4159	1.1471	0.037*
N3A	0.5984 (4)	0.33572 (10)	1.0033 (3)	0.0234 (6)
H3A	0.5375	0.3637	0.9584	0.028*
C4A	0.5718 (4)	0.28787 (13)	0.9342 (3)	0.0225 (7)
O41A	0.4577 (3)	0.28704 (9)	0.8053 (2)	0.0271 (5)
C5A	0.6701 (5)	0.24490 (13)	1.0084 (3)	0.0258 (7)
H5A	0.6584	0.2111	0.9648	0.031*
C6A	0.7865 (5)	0.25253 (13)	1.1483 (3)	0.0244 (7)
N61A	0.8847 (5)	0.21230 (11)	1.2270 (3)	0.0343 (7)
H61A	0.9583	0.2180	1.3152	0.041*
H61B	0.8754	0.1804	1.1902	0.041*
N1B	0.0210 (4)	0.41264 (10)	0.4808 (3)	0.0244 (6)
C2B	0.1126 (5)	0.37170 (13)	0.5545 (4)	0.0247 (7)
N21B	0.0823 (4)	0.32310 (11)	0.4976 (3)	0.0355 (8)
H21C	0.0015	0.3184	0.4113	0.043*
H21D	0.1431	0.2959	0.5465	0.043*
N3B	0.2387 (4)	0.37622 (11)	0.6873 (3)	0.0251 (6)
H3B	0.2939	0.3475	0.7315	0.030*
C4B	0.2846 (4)	0.42482 (13)	0.7568 (3)	0.0239 (7)
O41B	0.4079 (3)	0.42458 (9)	0.8790 (2)	0.0294 (5)
C5B	0.1879 (5)	0.46809 (12)	0.6809 (3)	0.0254 (7)
H5B	0.2092	0.5024	0.7218	0.030*
C6B	0.0601 (4)	0.46080 (12)	0.5451 (3)	0.0243 (7)
N61B	−0.0332 (4)	0.50164 (11)	0.4664 (3)	0.0308 (7)
H61C	−0.1126	0.4961	0.3801	0.037*
H61D	−0.0149	0.5339	0.5013	0.037*
N1C	0.4907 (4)	0.67315 (10)	0.4594 (3)	0.0249 (6)
C2C	0.3199 (5)	0.69608 (12)	0.4176 (3)	0.0240 (7)
N21C	0.2941 (4)	0.74136 (11)	0.3448 (3)	0.0321 (7)
H21E	0.3894	0.7561	0.3242	0.038*
H21F	0.1818	0.7565	0.3173	0.038*
N3C	0.1680 (4)	0.67483 (10)	0.4451 (3)	0.0230 (6)
H3C	0.0588	0.6915	0.4141	0.028*
C4C	0.1772 (4)	0.62771 (12)	0.5203 (3)	0.0219 (7)
O41C	0.0290 (3)	0.61173 (9)	0.5426 (2)	0.0296 (5)
C5C	0.3521 (4)	0.60245 (13)	0.5609 (3)	0.0241 (7)
H5C	0.3676	0.5693	0.6083	0.029*
C6C	0.5052 (4)	0.62643 (13)	0.5312 (3)	0.0244 (7)
N61C	0.6760 (4)	0.60401 (12)	0.5731 (3)	0.0384 (8)
H61E	0.7713	0.6194	0.5540	0.046*
H61F	0.6935	0.5739	0.6198	0.046*
O1V	0.2076 (3)	0.21935 (9)	0.6207 (3)	0.0271 (5)
H1V	0.271 (4)	0.2005 (12)	0.582 (3)	0.033*
H2V	0.278 (4)	0.2343 (13)	0.695 (2)	0.033*
C1W	0.9054 (6)	0.07825 (17)	1.0454 (4)	0.0463 (10)
H1W	0.9686	0.0643	1.1377	0.056*
O1W	0.8781 (5)	0.12587 (12)	1.0368 (3)	0.0677 (10)
N2W	0.8550 (5)	0.04439 (12)	0.9379 (3)	0.0374 (7)
C3W	0.7545 (8)	0.0628 (2)	0.7942 (5)	0.0633 (13)
H3W1	0.6252	0.0487	0.7638	0.095*
H3W2	0.8205	0.0506	0.7283	0.095*
H3W3	0.7499	0.1015	0.7934	0.095*
C4W	0.8889 (7)	−0.01146 (16)	0.9573 (5)	0.0553 (12)
H4W1	0.9636	−0.0186	1.0570	0.083*
H4W2	0.9588	−0.0237	0.8941	0.083*
H4W3	0.7676	−0.0301	0.9341	0.083*
C1X	−0.3644 (5)	0.52639 (15)	0.0612 (4)	0.0369 (9)
H1X	−0.4160	0.5085	−0.0274	0.044*
O1X	−0.3195 (4)	0.49928 (10)	0.1693 (3)	0.0489 (7)
N2X	−0.3477 (5)	0.57831 (12)	0.0562 (3)	0.0354 (7)
C3X	−0.2729 (8)	0.60950 (18)	0.1845 (5)	0.0715 (16)
H3X1	−0.2482	0.5866	0.2685	0.107*
H3X2	−0.3652	0.6367	0.1878	0.107*
H3X3	−0.1546	0.6264	0.1842	0.107*
C4X	−0.4038 (7)	0.60669 (19)	−0.0786 (4)	0.0546 (11)
H4X1	−0.4422	0.5814	−0.1579	0.082*
H4X2	−0.2967	0.6277	−0.0860	0.082*
H4X3	−0.5102	0.6301	−0.0828	0.082*
O1Y	0.7001 (4)	0.50147 (10)	0.7197 (3)	0.0422 (6)
N2Y	0.6245 (5)	0.42567 (14)	0.5915 (4)	0.0449 (9)
C1Y	0.7052 (8)	0.4531 (2)	0.7037 (6)	0.0360 (16)	0.672 (7)
H1Y	0.7785	0.4338	0.7850	0.043*	0.672 (7)
C3Y	0.6374 (10)	0.3704 (2)	0.5740 (8)	0.0472 (19)	0.672 (7)
H3YA	0.5587	0.3603	0.4775	0.071*	0.672 (7)
H3YB	0.5929	0.3520	0.6448	0.071*	0.672 (7)
H3YC	0.7695	0.3608	0.5877	0.071*	0.672 (7)
C4Y	0.5013 (8)	0.4555 (2)	0.4568 (6)	0.0419 (16)	0.672 (7)
H4YA	0.4469	0.4302	0.3795	0.063*	0.672 (7)
H4YB	0.5800	0.4810	0.4265	0.063*	0.672 (7)
H4YC	0.3989	0.4742	0.4792	0.063*	0.672 (7)
C1Y'	0.620 (2)	0.4736 (6)	0.6093 (17)	0.055 (4)*	0.328 (7)
H1Y'	0.5444	0.4928	0.5285	0.067*	0.328 (7)
C3Y'	0.557 (3)	0.3896 (8)	0.493 (2)	0.079 (6)*	0.328 (7)
H3YD	0.5932	0.3544	0.5341	0.118*	0.328 (7)
H3YE	0.6084	0.3951	0.4140	0.118*	0.328 (7)
H3YF	0.4184	0.3922	0.4567	0.118*	0.328 (7)
C4Y'	0.757 (2)	0.3919 (6)	0.7360 (14)	0.054 (4)*	0.328 (7)
H4YD	0.7488	0.3540	0.7145	0.081*	0.328 (7)
H4YE	0.7101	0.3987	0.8167	0.081*	0.328 (7)
H4YF	0.8894	0.4033	0.7609	0.081*	0.328 (7)
C1Z	−0.1313 (6)	0.7652 (2)	0.0294 (5)	0.0517 (11)
H1Z	−0.1460	0.7280	0.0278	0.062*
O1Z	−0.0400 (5)	0.78640 (15)	0.1449 (4)	0.0672 (10)
N2Z	−0.2084 (5)	0.79134 (14)	−0.0904 (4)	0.0443 (8)
C3Z	−0.1892 (7)	0.84789 (19)	−0.0986 (6)	0.0606 (13)
H3Z1	−0.1202	0.8618	−0.0035	0.091*
H3Z2	−0.3152	0.8641	−0.1328	0.091*
H3Z3	−0.1192	0.8562	−0.1650	0.091*
C4Z	−0.3169 (7)	0.7644 (2)	−0.2203 (5)	0.0634 (14)
H4Z1	−0.3156	0.7263	−0.2024	0.095*
H4Z2	−0.2607	0.7714	−0.2959	0.095*
H4Z3	−0.4479	0.7772	−0.2504	0.095*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0312 (16)	0.0217 (15)	0.0244 (15)	−0.0002 (12)	0.0082 (12)	−0.0012 (12)
C2A	0.0279 (17)	0.0205 (17)	0.0204 (17)	−0.0017 (14)	0.0073 (14)	−0.0010 (13)
N21A	0.0394 (17)	0.0223 (16)	0.0238 (15)	0.0036 (12)	−0.0002 (13)	−0.0015 (12)
N3A	0.0242 (14)	0.0208 (14)	0.0230 (15)	0.0037 (11)	0.0042 (11)	−0.0009 (11)
C4A	0.0224 (17)	0.0231 (17)	0.0227 (17)	−0.0037 (13)	0.0083 (14)	−0.0055 (14)
O41A	0.0250 (12)	0.0289 (13)	0.0245 (13)	0.0019 (10)	0.0035 (10)	−0.0067 (10)
C5A	0.0284 (18)	0.0219 (17)	0.0275 (18)	−0.0026 (14)	0.0095 (14)	−0.0054 (14)
C6A	0.0263 (18)	0.0223 (17)	0.0258 (17)	−0.0008 (14)	0.0098 (14)	0.0036 (14)
N61A	0.0452 (19)	0.0227 (15)	0.0285 (16)	0.0016 (13)	0.0025 (14)	0.0015 (12)
N1B	0.0270 (15)	0.0212 (15)	0.0219 (14)	0.0014 (11)	0.0030 (11)	−0.0003 (11)
C2B	0.0248 (18)	0.0229 (17)	0.0257 (18)	−0.0014 (14)	0.0069 (14)	−0.0015 (14)
N21B	0.0461 (19)	0.0232 (16)	0.0243 (16)	0.0063 (13)	−0.0073 (14)	−0.0026 (12)
N3B	0.0274 (15)	0.0221 (14)	0.0210 (15)	0.0050 (11)	0.0008 (12)	0.0008 (11)
C4B	0.0231 (16)	0.0233 (17)	0.0259 (18)	−0.0012 (14)	0.0084 (15)	−0.0040 (14)
O41B	0.0324 (13)	0.0273 (13)	0.0223 (12)	0.0010 (10)	0.0000 (11)	−0.0019 (9)
C5B	0.0291 (18)	0.0205 (17)	0.0253 (18)	−0.0026 (14)	0.0068 (15)	−0.0049 (13)
C6B	0.0236 (18)	0.0235 (18)	0.0267 (18)	−0.0010 (14)	0.0092 (15)	0.0035 (14)
N61B	0.0372 (18)	0.0202 (15)	0.0294 (15)	0.0023 (12)	0.0026 (13)	0.0001 (12)
N1C	0.0235 (15)	0.0244 (15)	0.0291 (15)	0.0015 (11)	0.0115 (12)	0.0045 (12)
C2C	0.0277 (18)	0.0212 (17)	0.0245 (17)	−0.0022 (14)	0.0100 (14)	−0.0018 (14)
N21C	0.0280 (16)	0.0261 (16)	0.0466 (18)	0.0045 (12)	0.0183 (14)	0.0114 (13)
N3C	0.0168 (13)	0.0233 (14)	0.0305 (15)	0.0023 (10)	0.0097 (11)	0.0025 (11)
C4C	0.0222 (16)	0.0205 (16)	0.0247 (16)	−0.0017 (13)	0.0100 (13)	−0.0029 (13)
O41C	0.0202 (12)	0.0252 (12)	0.0479 (14)	−0.0029 (9)	0.0172 (11)	0.0027 (11)
C5C	0.0202 (16)	0.0248 (17)	0.0297 (17)	−0.0002 (13)	0.0112 (13)	0.0024 (14)
C6C	0.0225 (16)	0.0272 (17)	0.0261 (17)	0.0007 (14)	0.0114 (13)	0.0022 (14)
N61C	0.0222 (15)	0.0405 (18)	0.057 (2)	0.0059 (13)	0.0185 (14)	0.0213 (16)
O1V	0.0241 (12)	0.0223 (12)	0.0364 (14)	−0.0002 (9)	0.0117 (10)	−0.0084 (10)
C1W	0.058 (3)	0.042 (3)	0.039 (2)	0.006 (2)	0.015 (2)	0.0015 (19)
O1W	0.104 (3)	0.0365 (19)	0.0548 (19)	0.0162 (18)	0.0140 (18)	−0.0074 (14)
N2W	0.0467 (19)	0.0311 (17)	0.0369 (17)	0.0042 (14)	0.0165 (15)	0.0044 (14)
C3W	0.093 (4)	0.054 (3)	0.039 (2)	−0.003 (3)	0.016 (3)	0.003 (2)
C4W	0.074 (3)	0.029 (2)	0.072 (3)	0.002 (2)	0.036 (3)	0.001 (2)
C1X	0.039 (2)	0.034 (2)	0.032 (2)	0.0044 (16)	0.0032 (17)	−0.0073 (17)
O1X	0.071 (2)	0.0271 (14)	0.0358 (15)	0.0066 (13)	−0.0007 (13)	0.0029 (13)
N2X	0.0474 (19)	0.0259 (16)	0.0268 (16)	0.0000 (13)	0.0030 (14)	−0.0027 (13)
C3X	0.114 (4)	0.032 (2)	0.045 (3)	−0.008 (3)	−0.007 (3)	−0.013 (2)
C4X	0.076 (3)	0.048 (3)	0.038 (2)	0.007 (2)	0.017 (2)	0.008 (2)
O1Y	0.0476 (16)	0.0308 (16)	0.0495 (16)	0.0011 (12)	0.0174 (13)	0.0018 (13)
N2Y	0.047 (2)	0.037 (2)	0.061 (2)	−0.0071 (16)	0.0316 (18)	−0.0101 (18)
C1Y	0.038 (3)	0.032 (3)	0.041 (4)	0.001 (2)	0.017 (3)	0.008 (3)
C3Y	0.056 (4)	0.026 (3)	0.072 (5)	−0.006 (3)	0.039 (4)	−0.009 (3)
C4Y	0.038 (3)	0.049 (4)	0.039 (3)	0.002 (3)	0.013 (3)	0.004 (3)
C1Z	0.045 (3)	0.058 (3)	0.060 (3)	0.015 (2)	0.028 (2)	0.014 (2)
O1Z	0.055 (2)	0.092 (3)	0.055 (2)	0.0329 (19)	0.0173 (17)	0.0070 (19)
N2Z	0.0366 (19)	0.048 (2)	0.053 (2)	0.0067 (15)	0.0205 (17)	0.0080 (17)
C3Z	0.059 (3)	0.048 (3)	0.087 (4)	0.012 (2)	0.040 (3)	0.015 (3)
C4Z	0.053 (3)	0.086 (4)	0.053 (3)	0.005 (3)	0.021 (2)	0.003 (3)

Geometric parameters (Å, º) top

N1A—C2A	1.325 (4)	N2W—C3W	1.454 (5)
N1A—C6A	1.368 (4)	C3W—H3W1	0.9800
C2A—N21A	1.338 (4)	C3W—H3W2	0.9800
C2A—N3A	1.359 (4)	C3W—H3W3	0.9800
N21A—H21A	0.8800	C4W—H4W1	0.9800
N21A—H21B	0.8800	C4W—H4W2	0.9800
N3A—C4A	1.373 (4)	C4W—H4W3	0.9800
N3A—H3A	0.8800	C1X—O1X	1.221 (4)
C4A—O41A	1.285 (4)	C1X—N2X	1.323 (5)
C4A—C5A	1.384 (5)	C1X—H1X	0.9500
C5A—C6A	1.390 (4)	N2X—C3X	1.445 (5)
C5A—H5A	0.9500	N2X—C4X	1.450 (5)
C6A—N61A	1.347 (4)	C3X—H3X1	0.9800
N61A—H61A	0.8800	C3X—H3X2	0.9800
N61A—H61B	0.8800	C3X—H3X3	0.9800
N1B—C2B	1.324 (4)	C4X—H4X1	0.9800
N1B—C6B	1.363 (4)	C4X—H4X2	0.9800
C2B—N21B	1.341 (4)	C4X—H4X3	0.9800
C2B—N3B	1.352 (4)	O1Y—C1Y	1.237 (6)
N21B—H21C	0.8800	O1Y—C1Y'	1.276 (15)
N21B—H21D	0.8800	N2Y—C1Y'	1.227 (16)
N3B—C4B	1.397 (4)	N2Y—C1Y	1.283 (7)
N3B—H3B	0.8800	N2Y—C3Y'	1.313 (19)
C4B—O41B	1.262 (4)	N2Y—C3Y	1.416 (7)
C4B—C5B	1.392 (5)	N2Y—C4Y	1.550 (7)
C5B—C6B	1.387 (5)	N2Y—C4Y'	1.687 (14)
C5B—H5B	0.9500	C1Y—H1Y	0.9500
C6B—N61B	1.346 (4)	C3Y—H3YA	0.9800
N61B—H61C	0.8800	C3Y—H3YB	0.9800
N61B—H61D	0.8800	C3Y—H3YC	0.9800
N1C—C2C	1.338 (4)	C4Y—H4YA	0.9800
N1C—C6C	1.365 (4)	C4Y—H4YB	0.9800
C2C—N21C	1.334 (4)	C4Y—H4YC	0.9800
C2C—N3C	1.354 (4)	C1Y'—H1Y'	0.9500
N21C—H21E	0.8800	C3Y'—H3YD	0.9800
N21C—H21F	0.8800	C3Y'—H3YE	0.9800
N3C—C4C	1.395 (4)	C3Y'—H3YF	0.9800
N3C—H3C	0.8800	C4Y'—H4YD	0.9800
C4C—O41C	1.258 (4)	C4Y'—H4YE	0.9800
C4C—C5C	1.390 (4)	C4Y'—H4YF	0.9800
C5C—C6C	1.402 (4)	C1Z—O1Z	1.247 (6)
C5C—H5C	0.9500	C1Z—N2Z	1.316 (6)
C6C—N61C	1.333 (4)	C1Z—H1Z	0.9500
N61C—H61E	0.8800	N2Z—C3Z	1.444 (6)
N61C—H61F	0.8800	N2Z—C4Z	1.450 (6)
O1V—H1V	0.844 (10)	C3Z—H3Z1	0.9800
O1V—H2V	0.844 (10)	C3Z—H3Z2	0.9800
C1W—O1W	1.222 (5)	C3Z—H3Z3	0.9800
C1W—N2W	1.321 (5)	C4Z—H4Z1	0.9800
C1W—H1W	0.9500	C4Z—H4Z2	0.9800
N2W—C4W	1.439 (5)	C4Z—H4Z3	0.9800

C2A—N1A—C6A	116.5 (3)	H4W1—C4W—H4W3	109.5
N1A—C2A—N21A	119.9 (3)	H4W2—C4W—H4W3	109.5
N1A—C2A—N3A	123.0 (3)	O1X—C1X—N2X	126.1 (3)
N21A—C2A—N3A	117.1 (3)	O1X—C1X—H1X	117.0
C2A—N21A—H21A	120.0	N2X—C1X—H1X	117.0
C2A—N21A—H21B	120.0	C1X—N2X—C3X	121.7 (3)
H21A—N21A—H21B	120.0	C1X—N2X—C4X	121.6 (3)
C2A—N3A—C4A	121.3 (3)	C3X—N2X—C4X	116.7 (3)
C2A—N3A—H3A	119.3	N2X—C3X—H3X1	109.5
C4A—N3A—H3A	119.3	N2X—C3X—H3X2	109.5
O41A—C4A—N3A	116.8 (3)	H3X1—C3X—H3X2	109.5
O41A—C4A—C5A	125.6 (3)	N2X—C3X—H3X3	109.5
N3A—C4A—C5A	117.6 (3)	H3X1—C3X—H3X3	109.5
C4A—C5A—C6A	118.3 (3)	H3X2—C3X—H3X3	109.5
C4A—C5A—H5A	120.9	N2X—C4X—H4X1	109.5
C6A—C5A—H5A	120.9	N2X—C4X—H4X2	109.5
N61A—C6A—N1A	115.4 (3)	H4X1—C4X—H4X2	109.5
N61A—C6A—C5A	121.3 (3)	N2X—C4X—H4X3	109.5
N1A—C6A—C5A	123.2 (3)	H4X1—C4X—H4X3	109.5
C6A—N61A—H61A	120.0	H4X2—C4X—H4X3	109.5
C6A—N61A—H61B	120.0	C1Y—O1Y—C1Y'	50.8 (7)
H61A—N61A—H61B	120.0	C1Y'—N2Y—C1Y	50.9 (8)
C2B—N1B—C6B	116.7 (3)	C1Y'—N2Y—C3Y'	140.5 (13)
N1B—C2B—N21B	120.0 (3)	C1Y—N2Y—C3Y'	168.6 (10)
N1B—C2B—N3B	122.9 (3)	C1Y'—N2Y—C3Y	177.9 (9)
N21B—C2B—N3B	117.1 (3)	C1Y—N2Y—C3Y	127.5 (5)
C2B—N21B—H21C	120.0	C1Y'—N2Y—C4Y	66.7 (8)
C2B—N21B—H21D	120.0	C1Y—N2Y—C4Y	117.6 (4)
H21C—N21B—H21D	120.0	C3Y'—N2Y—C4Y	73.8 (10)
C2B—N3B—C4B	122.4 (3)	C3Y—N2Y—C4Y	114.9 (5)
C2B—N3B—H3B	118.8	C1Y'—N2Y—C4Y'	114.6 (9)
C4B—N3B—H3B	118.8	C1Y—N2Y—C4Y'	63.7 (6)
O41B—C4B—C5B	127.8 (3)	C3Y'—N2Y—C4Y'	104.9 (11)
O41B—C4B—N3B	117.1 (3)	C3Y—N2Y—C4Y'	63.7 (6)
C5B—C4B—N3B	115.2 (3)	C4Y—N2Y—C4Y'	178.7 (6)
C6B—C5B—C4B	119.6 (3)	O1Y—C1Y—N2Y	128.4 (5)
C6B—C5B—H5B	120.2	O1Y—C1Y—H1Y	115.8
C4B—C5B—H5B	120.2	N2Y—C1Y—H1Y	115.8
N61B—C6B—N1B	115.1 (3)	N2Y—C3Y—H3YA	109.5
N61B—C6B—C5B	121.6 (3)	N2Y—C3Y—H3YB	109.5
N1B—C6B—C5B	123.2 (3)	H3YA—C3Y—H3YB	109.5
C6B—N61B—H61C	120.0	N2Y—C3Y—H3YC	109.5
C6B—N61B—H61D	120.0	H3YA—C3Y—H3YC	109.5
H61C—N61B—H61D	120.0	H3YB—C3Y—H3YC	109.5
C2C—N1C—C6C	116.5 (3)	N2Y—C4Y—H4YA	109.5
N21C—C2C—N1C	119.9 (3)	N2Y—C4Y—H4YB	109.5
N21C—C2C—N3C	117.5 (3)	H4YA—C4Y—H4YB	109.5
N1C—C2C—N3C	122.5 (3)	N2Y—C4Y—H4YC	109.5
C2C—N21C—H21E	120.0	H4YA—C4Y—H4YC	109.5
C2C—N21C—H21F	120.0	H4YB—C4Y—H4YC	109.5
H21E—N21C—H21F	120.0	N2Y—C1Y'—O1Y	130.0 (14)
C2C—N3C—C4C	122.9 (3)	N2Y—C1Y'—H1Y'	115.0
C2C—N3C—H3C	118.6	O1Y—C1Y'—H1Y'	115.0
C4C—N3C—H3C	118.6	N2Y—C3Y'—H3YD	109.5
O41C—C4C—C5C	126.4 (3)	N2Y—C3Y'—H3YE	109.5
O41C—C4C—N3C	118.1 (3)	H3YD—C3Y'—H3YE	109.5
C5C—C4C—N3C	115.5 (3)	N2Y—C3Y'—H3YF	109.5
C4C—C5C—C6C	119.3 (3)	H3YD—C3Y'—H3YF	109.5
C4C—C5C—H5C	120.3	H3YE—C3Y'—H3YF	109.5
C6C—C5C—H5C	120.3	N2Y—C4Y'—H4YD	109.5
N61C—C6C—N1C	116.1 (3)	N2Y—C4Y'—H4YE	109.5
N61C—C6C—C5C	120.6 (3)	H4YD—C4Y'—H4YE	109.5
N1C—C6C—C5C	123.2 (3)	N2Y—C4Y'—H4YF	109.5
C6C—N61C—H61E	120.0	H4YD—C4Y'—H4YF	109.5
C6C—N61C—H61F	120.0	H4YE—C4Y'—H4YF	109.5
H61E—N61C—H61F	120.0	O1Z—C1Z—N2Z	124.1 (5)
H1V—O1V—H2V	111.3 (17)	O1Z—C1Z—H1Z	117.9
O1W—C1W—N2W	125.9 (4)	N2Z—C1Z—H1Z	117.9
O1W—C1W—H1W	117.1	C1Z—N2Z—C3Z	121.7 (4)
N2W—C1W—H1W	117.1	C1Z—N2Z—C4Z	121.2 (4)
C1W—N2W—C4W	122.5 (4)	C3Z—N2Z—C4Z	117.1 (4)
C1W—N2W—C3W	120.1 (4)	N2Z—C3Z—H3Z1	109.5
C4W—N2W—C3W	117.3 (4)	N2Z—C3Z—H3Z2	109.5
N2W—C3W—H3W1	109.5	H3Z1—C3Z—H3Z2	109.5
N2W—C3W—H3W2	109.5	N2Z—C3Z—H3Z3	109.5
H3W1—C3W—H3W2	109.5	H3Z1—C3Z—H3Z3	109.5
N2W—C3W—H3W3	109.5	H3Z2—C3Z—H3Z3	109.5
H3W1—C3W—H3W3	109.5	N2Z—C4Z—H4Z1	109.5
H3W2—C3W—H3W3	109.5	N2Z—C4Z—H4Z2	109.5
N2W—C4W—H4W1	109.5	H4Z1—C4Z—H4Z2	109.5
N2W—C4W—H4W2	109.5	N2Z—C4Z—H4Z3	109.5
H4W1—C4W—H4W2	109.5	H4Z1—C4Z—H4Z3	109.5
N2W—C4W—H4W3	109.5	H4Z2—C4Z—H4Z3	109.5

C6A—N1A—C2A—N21A	−179.0 (3)	N1C—C2C—N3C—C4C	0.7 (5)
C6A—N1A—C2A—N3A	1.3 (5)	C2C—N3C—C4C—O41C	178.7 (3)
N1A—C2A—N3A—C4A	−1.3 (5)	C2C—N3C—C4C—C5C	−2.5 (4)
N21A—C2A—N3A—C4A	179.0 (3)	O41C—C4C—C5C—C6C	−178.2 (3)
C2A—N3A—C4A—O41A	−179.7 (3)	N3C—C4C—C5C—C6C	3.1 (4)
C2A—N3A—C4A—C5A	0.0 (4)	C2C—N1C—C6C—N61C	−179.6 (3)
O41A—C4A—C5A—C6A	−179.2 (3)	C2C—N1C—C6C—C5C	0.3 (4)
N3A—C4A—C5A—C6A	1.1 (4)	C4C—C5C—C6C—N61C	177.8 (3)
C2A—N1A—C6A—N61A	179.5 (3)	C4C—C5C—C6C—N1C	−2.2 (5)
C2A—N1A—C6A—C5A	−0.1 (5)	O1W—C1W—N2W—C4W	−178.7 (5)
C4A—C5A—C6A—N61A	179.3 (3)	O1W—C1W—N2W—C3W	−1.2 (7)
C4A—C5A—C6A—N1A	−1.1 (5)	O1X—C1X—N2X—C3X	−0.7 (7)
C6B—N1B—C2B—N21B	−179.6 (3)	O1X—C1X—N2X—C4X	179.3 (4)
C6B—N1B—C2B—N3B	0.3 (5)	C1Y'—O1Y—C1Y—N2Y	0.6 (9)
N1B—C2B—N3B—C4B	−0.9 (5)	C1Y'—N2Y—C1Y—O1Y	−0.6 (10)
N21B—C2B—N3B—C4B	178.9 (3)	C3Y'—N2Y—C1Y—O1Y	−178 (5)
C2B—N3B—C4B—O41B	−178.2 (3)	C3Y—N2Y—C1Y—O1Y	177.7 (5)
C2B—N3B—C4B—C5B	1.4 (4)	C4Y—N2Y—C1Y—O1Y	−0.8 (8)
O41B—C4B—C5B—C6B	178.2 (3)	C4Y'—N2Y—C1Y—O1Y	179.3 (9)
N3B—C4B—C5B—C6B	−1.3 (4)	C1Y—N2Y—C1Y'—O1Y	0.6 (10)
C2B—N1B—C6B—N61B	179.0 (3)	C3Y'—N2Y—C1Y'—O1Y	179.8 (15)
C2B—N1B—C6B—C5B	−0.2 (5)	C4Y—N2Y—C1Y'—O1Y	−179.6 (18)
C4B—C5B—C6B—N61B	−178.4 (3)	C4Y'—N2Y—C1Y'—O1Y	0.5 (19)
C4B—C5B—C6B—N1B	0.8 (5)	C1Y—O1Y—C1Y'—N2Y	−0.6 (10)
C6C—N1C—C2C—N21C	−178.9 (3)	O1Z—C1Z—N2Z—C3Z	1.5 (6)
C6C—N1C—C2C—N3C	0.4 (4)	O1Z—C1Z—N2Z—C4Z	−178.4 (4)
N21C—C2C—N3C—C4C	−180.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N1Bⁱ	0.88	2.11	2.985 (4)	170
N21A—H21B···O1Xⁱ	0.88	2.12	2.820 (4)	136
N3A—H3A···O41B	0.88	1.86	2.734 (3)	175
N61A—H61B···O1W	0.88	2.05	2.872 (4)	155
N21B—H21C···N1Aⁱⁱ	0.88	2.05	2.931 (4)	175
N21B—H21D···O1V	0.88	2.07	2.920 (4)	161
N3B—H3B···O41A	0.88	1.95	2.812 (3)	167
N61B—H61C···O1X	0.88	2.16	3.028 (4)	168
N61B—H61D···O41C	0.88	2.02	2.886 (4)	169
N21C—H21E···O41Aⁱⁱⁱ	0.88	2.11	2.945 (4)	158
N21C—H21F···O1Z	0.88	2.10	2.874 (4)	146
N3C—H3C···O1V^iv	0.88	2.03	2.890 (3)	166
N61C—H61E···O41C^v	0.88	1.97	2.744 (3)	147
N61C—H61F···O1Y	0.88	2.07	2.949 (4)	173
O1V—H1V···N1C^vi	0.84 (1)	2.06 (2)	2.856 (3)	157 (3)
O1V—H2V···O41A	0.84 (1)	1.96 (2)	2.751 (3)	156 (4)

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

(Ib) 2,6-diaminopyrimidin-4-one dimethylacetamide solvate (1/1) top

Crystal data top

C₄H₆N₄O·C₄H₉NO	F(000) = 912
M_r = 213.25	D_x = 1.304 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 10399 reflections
a = 19.1494 (13) Å	θ = 3.3–26°
b = 7.8704 (4) Å	µ = 0.10 mm⁻¹
c = 14.9104 (11) Å	T = 173 K
β = 104.868 (6)°	Block, colourless
V = 2172.0 (2) Å³	0.50 × 0.35 × 0.30 mm
Z = 8

Data collection top

Stoe IPDS II two-circle diffractometer	1922 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.096
Graphite monochromator	θ_max = 25.6°, θ_min = 3.3°
ω scans	h = −23→23
12494 measured reflections	k = −9→9
2054 independent reflections	l = −18→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0831P)² + 1.0447P] where P = (F_o² + 2F_c²)/3
2054 reflections	(Δ/σ)_max < 0.001
277 parameters	Δρ_max = 0.47 e Å⁻³
22 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₄H₆N₄O·C₄H₉NO	V = 2172.0 (2) Å³
M_r = 213.25	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 19.1494 (13) Å	µ = 0.10 mm⁻¹
b = 7.8704 (4) Å	T = 173 K
c = 14.9104 (11) Å	0.50 × 0.35 × 0.30 mm
β = 104.868 (6)°

Data collection top

Stoe IPDS II two-circle diffractometer	1922 reflections with I > 2σ(I)
12494 measured reflections	R_int = 0.096
2054 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	22 restraints
wR(F²) = 0.126	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
2054 reflections	Δρ_min = −0.31 e Å⁻³
277 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
N1A	0.61616 (13)	0.5230 (3)	0.58590 (17)	0.0210 (6)
C2A	0.63414 (16)	0.6155 (4)	0.5207 (2)	0.0201 (6)
N21A	0.58328 (15)	0.6543 (4)	0.44317 (19)	0.0285 (7)
H21A	0.5386	0.6186	0.4360	0.034*
H21B	0.5946	0.7154	0.3995	0.034*
N3A	0.70167 (14)	0.6750 (3)	0.52842 (18)	0.0212 (5)
H3A	0.7104	0.7333	0.4821	0.025*
C4A	0.75747 (16)	0.6473 (4)	0.6067 (2)	0.0217 (6)
O41A	0.81938 (12)	0.7060 (3)	0.60727 (15)	0.0282 (5)
C5A	0.74048 (17)	0.5564 (4)	0.6787 (2)	0.0232 (7)
H5A	0.7756	0.5390	0.7359	0.028*
C6A	0.67048 (17)	0.4916 (4)	0.6645 (2)	0.0206 (6)
N61A	0.65267 (15)	0.3953 (4)	0.7290 (2)	0.0292 (6)
H61A	0.6083	0.3562	0.7198	0.035*
H61B	0.6853	0.3710	0.7808	0.035*
N1B	0.43760 (14)	0.5051 (3)	0.40727 (17)	0.0202 (6)
C2B	0.41736 (15)	0.4106 (4)	0.4692 (2)	0.0197 (6)
N21B	0.46672 (15)	0.3675 (4)	0.5479 (2)	0.0313 (7)
H21C	0.5117	0.4024	0.5574	0.038*
H21D	0.4540	0.3045	0.5899	0.038*
N3B	0.34909 (15)	0.3540 (3)	0.45794 (19)	0.0221 (6)
H3B	0.3393	0.2903	0.5016	0.026*
C4B	0.29359 (16)	0.3925 (4)	0.3799 (2)	0.0211 (6)
O41B	0.23111 (12)	0.3381 (3)	0.37796 (16)	0.0281 (5)
C5B	0.31392 (17)	0.4896 (4)	0.3126 (2)	0.0237 (7)
H5B	0.2794	0.5180	0.2565	0.028*
C6B	0.38518 (17)	0.5448 (4)	0.3282 (2)	0.0215 (6)
N61B	0.40751 (15)	0.6384 (4)	0.2662 (2)	0.0266 (6)
H61C	0.4530	0.6701	0.2776	0.032*
H61D	0.3767	0.6684	0.2140	0.032*
C1X	0.5954 (3)	1.0338 (6)	0.1704 (4)	0.0489 (11)
H1X1	0.6384	1.0923	0.2076	0.073*
H1X2	0.5691	1.1096	0.1212	0.073*
H1X3	0.6102	0.9314	0.1427	0.073*
C2X	0.54723 (18)	0.9847 (4)	0.2318 (3)	0.0316 (7)
O2X	0.53495 (14)	0.8322 (3)	0.2457 (2)	0.0343 (6)
N3X	0.51898 (18)	1.1078 (4)	0.2722 (2)	0.0378 (7)
C4X	0.4720 (3)	1.0644 (6)	0.3330 (4)	0.0617 (14)
H4X1	0.4217	1.0582	0.2961	0.093*
H4X2	0.4764	1.1520	0.3809	0.093*
H4X3	0.4865	0.9542	0.3625	0.093*
C5X	0.5291 (3)	1.2891 (5)	0.2569 (4)	0.0534 (12)
H5X1	0.5635	1.3029	0.2188	0.080*
H5X2	0.5478	1.3458	0.3168	0.080*
H5X3	0.4826	1.3398	0.2248	0.080*
C1Y	0.8991 (3)	0.3714 (9)	0.5421 (4)	0.0775 (17)
H1Y1	0.9239	0.2632	0.5399	0.116*
H1Y2	0.8937	0.3900	0.6050	0.116*
H1Y3	0.9276	0.4642	0.5255	0.116*
C2Y	0.8241 (3)	0.3665 (7)	0.4731 (3)	0.0741 (18)
O2Y	0.8107 (3)	0.4576 (5)	0.4029 (2)	0.0796 (13)
N3Y	0.7765 (3)	0.2683 (6)	0.4930 (3)	0.0740 (14)
C4Y	0.7040 (3)	0.2654 (8)	0.4267 (5)	0.0778 (18)
H4Y1	0.7025	0.3487	0.3773	0.117*
H4Y2	0.6672	0.2939	0.4594	0.117*
H4Y3	0.6945	0.1518	0.3995	0.117*
C5Y	0.7886 (5)	0.1671 (7)	0.5786 (4)	0.085 (2)
H5Y1	0.8406	0.1585	0.6073	0.127*
H5Y2	0.7684	0.0531	0.5636	0.127*
H5Y3	0.7650	0.2223	0.6218	0.127*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0178 (13)	0.0237 (13)	0.0208 (13)	−0.0006 (10)	0.0040 (11)	0.0042 (10)
C2A	0.0179 (15)	0.0207 (14)	0.0213 (15)	−0.0042 (12)	0.0044 (12)	−0.0015 (12)
N21A	0.0176 (13)	0.0415 (16)	0.0236 (14)	−0.0072 (12)	0.0000 (11)	0.0121 (12)
N3A	0.0186 (12)	0.0261 (13)	0.0180 (12)	−0.0051 (10)	0.0034 (10)	0.0030 (10)
C4A	0.0179 (14)	0.0281 (16)	0.0189 (14)	−0.0030 (12)	0.0043 (11)	−0.0051 (12)
O41A	0.0208 (11)	0.0413 (14)	0.0213 (11)	−0.0122 (10)	0.0034 (8)	−0.0022 (10)
C5A	0.0174 (14)	0.0310 (16)	0.0184 (15)	0.0005 (12)	−0.0004 (11)	0.0016 (12)
C6A	0.0204 (15)	0.0248 (15)	0.0173 (15)	0.0033 (12)	0.0062 (12)	0.0010 (11)
N61A	0.0212 (14)	0.0380 (16)	0.0267 (14)	0.0002 (12)	0.0031 (11)	0.0117 (12)
N1B	0.0160 (12)	0.0249 (13)	0.0186 (13)	−0.0017 (10)	0.0023 (10)	0.0037 (10)
C2B	0.0175 (15)	0.0207 (14)	0.0203 (15)	−0.0012 (12)	0.0036 (12)	0.0005 (12)
N21B	0.0200 (14)	0.0450 (17)	0.0245 (15)	−0.0091 (12)	−0.0019 (12)	0.0142 (12)
N3B	0.0201 (13)	0.0247 (13)	0.0211 (13)	−0.0063 (11)	0.0047 (11)	0.0020 (11)
C4B	0.0179 (15)	0.0234 (15)	0.0206 (15)	−0.0024 (12)	0.0025 (12)	−0.0028 (12)
O41B	0.0187 (11)	0.0387 (14)	0.0255 (12)	−0.0079 (10)	0.0032 (9)	0.0010 (10)
C5B	0.0196 (16)	0.0308 (17)	0.0186 (15)	−0.0018 (13)	0.0012 (12)	0.0000 (12)
C6B	0.0208 (15)	0.0239 (15)	0.0190 (15)	0.0017 (12)	0.0037 (12)	0.0015 (12)
N61B	0.0155 (12)	0.0393 (16)	0.0233 (13)	−0.0002 (11)	0.0020 (10)	0.0143 (12)
C1X	0.048 (2)	0.040 (2)	0.069 (3)	−0.0004 (19)	0.035 (2)	0.010 (2)
C2X	0.0283 (17)	0.0281 (17)	0.0398 (18)	−0.0034 (14)	0.0111 (14)	0.0003 (14)
O2X	0.0330 (14)	0.0219 (11)	0.0531 (14)	−0.0003 (11)	0.0203 (11)	0.0023 (11)
N3X	0.0439 (17)	0.0233 (15)	0.0495 (19)	−0.0013 (13)	0.0180 (14)	−0.0019 (13)
C4X	0.082 (4)	0.041 (2)	0.082 (4)	0.006 (2)	0.057 (3)	−0.001 (2)
C5X	0.063 (3)	0.0232 (18)	0.079 (3)	−0.0035 (19)	0.027 (2)	−0.007 (2)
C1Y	0.082 (4)	0.073 (4)	0.070 (4)	0.011 (3)	0.006 (3)	−0.025 (3)
C2Y	0.126 (6)	0.047 (3)	0.056 (3)	0.009 (3)	0.038 (3)	−0.014 (2)
O2Y	0.143 (4)	0.058 (2)	0.0332 (16)	−0.018 (2)	0.0134 (19)	0.0036 (16)
N3Y	0.134 (4)	0.045 (2)	0.054 (2)	0.012 (3)	0.045 (2)	0.0016 (19)
C4Y	0.065 (3)	0.065 (4)	0.099 (5)	0.005 (3)	0.013 (3)	−0.032 (3)
C5Y	0.166 (7)	0.043 (3)	0.062 (3)	0.023 (4)	0.058 (4)	0.010 (2)

Geometric parameters (Å, º) top

N1A—C2A	1.329 (4)	N61B—H61D	0.8800
N1A—C6A	1.375 (4)	C1X—C2X	1.507 (5)
C2A—N21A	1.341 (4)	C1X—H1X1	0.9800
C2A—N3A	1.352 (4)	C1X—H1X2	0.9800
N21A—H21A	0.8800	C1X—H1X3	0.9800
N21A—H21B	0.8800	C2X—O2X	1.250 (4)
N3A—C4A	1.382 (4)	C2X—N3X	1.327 (4)
N3A—H3A	0.8800	N3X—C5X	1.466 (4)
C4A—O41A	1.270 (4)	N3X—C4X	1.472 (5)
C4A—C5A	1.397 (5)	C4X—H4X1	0.9800
C5A—C6A	1.399 (5)	C4X—H4X2	0.9800
C5A—H5A	0.9500	C4X—H4X3	0.9800
C6A—N61A	1.336 (4)	C5X—H5X1	0.9800
N61A—H61A	0.8800	C5X—H5X2	0.9800
N61A—H61B	0.8800	C5X—H5X3	0.9800
N1B—C2B	1.319 (4)	C1Y—C2Y	1.538 (7)
N1B—C6B	1.374 (4)	C1Y—H1Y1	0.9800
C2B—N21B	1.348 (4)	C1Y—H1Y2	0.9800
C2B—N3B	1.350 (4)	C1Y—H1Y3	0.9800
N21B—H21C	0.8800	C2Y—O2Y	1.241 (6)
N21B—H21D	0.8800	C2Y—N3Y	1.287 (6)
N3B—C4B	1.393 (4)	N3Y—C5Y	1.471 (6)
N3B—H3B	0.8800	N3Y—C4Y	1.483 (7)
C4B—O41B	1.264 (4)	C4Y—H4Y1	0.9800
C4B—C5B	1.395 (5)	C4Y—H4Y2	0.9800
C5B—C6B	1.393 (5)	C4Y—H4Y3	0.9800
C5B—H5B	0.9500	C5Y—H5Y1	0.9800
C6B—N61B	1.335 (4)	C5Y—H5Y2	0.9800
N61B—H61C	0.8800	C5Y—H5Y3	0.9800

C2A—N1A—C6A	116.2 (3)	H1X1—C1X—H1X2	109.5
N1A—C2A—N21A	119.2 (3)	C2X—C1X—H1X3	109.5
N1A—C2A—N3A	123.3 (3)	H1X1—C1X—H1X3	109.5
N21A—C2A—N3A	117.5 (3)	H1X2—C1X—H1X3	109.5
C2A—N21A—H21A	120.0	O2X—C2X—N3X	120.6 (3)
C2A—N21A—H21B	120.0	O2X—C2X—C1X	121.2 (3)
H21A—N21A—H21B	120.0	N3X—C2X—C1X	118.2 (3)
C2A—N3A—C4A	122.2 (3)	C2X—N3X—C5X	123.7 (3)
C2A—N3A—H3A	118.9	C2X—N3X—C4X	119.7 (3)
C4A—N3A—H3A	118.9	C5X—N3X—C4X	116.6 (3)
O41A—C4A—N3A	117.8 (3)	N3X—C4X—H4X1	109.5
O41A—C4A—C5A	125.6 (3)	N3X—C4X—H4X2	109.5
N3A—C4A—C5A	116.6 (3)	H4X1—C4X—H4X2	109.5
C4A—C5A—C6A	118.3 (3)	N3X—C4X—H4X3	109.5
C4A—C5A—H5A	120.9	H4X1—C4X—H4X3	109.5
C6A—C5A—H5A	120.9	H4X2—C4X—H4X3	109.5
N61A—C6A—N1A	116.0 (3)	N3X—C5X—H5X1	109.5
N61A—C6A—C5A	120.6 (3)	N3X—C5X—H5X2	109.5
N1A—C6A—C5A	123.3 (3)	H5X1—C5X—H5X2	109.5
C6A—N61A—H61A	120.0	N3X—C5X—H5X3	109.5
C6A—N61A—H61B	120.0	H5X1—C5X—H5X3	109.5
H61A—N61A—H61B	120.0	H5X2—C5X—H5X3	109.5
C2B—N1B—C6B	116.6 (3)	C2Y—C1Y—H1Y1	109.5
N1B—C2B—N21B	119.0 (3)	C2Y—C1Y—H1Y2	109.5
N1B—C2B—N3B	123.2 (3)	H1Y1—C1Y—H1Y2	109.5
N21B—C2B—N3B	117.7 (3)	C2Y—C1Y—H1Y3	109.5
C2B—N21B—H21C	120.0	H1Y1—C1Y—H1Y3	109.5
C2B—N21B—H21D	120.0	H1Y2—C1Y—H1Y3	109.5
H21C—N21B—H21D	120.0	O2Y—C2Y—N3Y	122.4 (6)
C2B—N3B—C4B	122.6 (3)	O2Y—C2Y—C1Y	120.4 (6)
C2B—N3B—H3B	118.7	N3Y—C2Y—C1Y	117.2 (5)
C4B—N3B—H3B	118.7	C2Y—N3Y—C5Y	124.1 (6)
O41B—C4B—N3B	117.4 (3)	C2Y—N3Y—C4Y	116.9 (5)
O41B—C4B—C5B	127.3 (3)	C5Y—N3Y—C4Y	118.9 (6)
N3B—C4B—C5B	115.2 (3)	N3Y—C4Y—H4Y1	109.5
C6B—C5B—C4B	119.5 (3)	N3Y—C4Y—H4Y2	109.5
C6B—C5B—H5B	120.2	H4Y1—C4Y—H4Y2	109.5
C4B—C5B—H5B	120.2	N3Y—C4Y—H4Y3	109.5
N61B—C6B—N1B	115.2 (3)	H4Y1—C4Y—H4Y3	109.5
N61B—C6B—C5B	122.0 (3)	H4Y2—C4Y—H4Y3	109.5
N1B—C6B—C5B	122.8 (3)	N3Y—C5Y—H5Y1	109.5
C6B—N61B—H61C	120.0	N3Y—C5Y—H5Y2	109.5
C6B—N61B—H61D	120.0	H5Y1—C5Y—H5Y2	109.5
H61C—N61B—H61D	120.0	N3Y—C5Y—H5Y3	109.5
C2X—C1X—H1X1	109.5	H5Y1—C5Y—H5Y3	109.5
C2X—C1X—H1X2	109.5	H5Y2—C5Y—H5Y3	109.5

C6A—N1A—C2A—N21A	−178.4 (3)	C2B—N3B—C4B—O41B	−177.5 (3)
C6A—N1A—C2A—N3A	0.9 (4)	C2B—N3B—C4B—C5B	1.9 (4)
N1A—C2A—N3A—C4A	−1.6 (5)	O41B—C4B—C5B—C6B	177.3 (3)
N21A—C2A—N3A—C4A	177.8 (3)	N3B—C4B—C5B—C6B	−2.0 (4)
C2A—N3A—C4A—O41A	179.0 (3)	C2B—N1B—C6B—N61B	−179.1 (3)
C2A—N3A—C4A—C5A	−1.0 (4)	C2B—N1B—C6B—C5B	0.0 (5)
O41A—C4A—C5A—C6A	−176.1 (3)	C4B—C5B—C6B—N61B	−179.8 (3)
N3A—C4A—C5A—C6A	3.9 (4)	C4B—C5B—C6B—N1B	1.2 (5)
C2A—N1A—C6A—N61A	−178.5 (3)	O2X—C2X—N3X—C5X	−178.0 (4)
C2A—N1A—C6A—C5A	2.3 (4)	C1X—C2X—N3X—C5X	3.2 (6)
C4A—C5A—C6A—N61A	176.0 (3)	O2X—C2X—N3X—C4X	−0.8 (6)
C4A—C5A—C6A—N1A	−4.8 (5)	C1X—C2X—N3X—C4X	−179.7 (5)
C6B—N1B—C2B—N21B	179.8 (3)	O2Y—C2Y—N3Y—C5Y	−175.7 (5)
C6B—N1B—C2B—N3B	−0.2 (4)	C1Y—C2Y—N3Y—C5Y	2.5 (7)
N1B—C2B—N3B—C4B	−0.8 (5)	O2Y—C2Y—N3Y—C4Y	1.2 (7)
N21B—C2B—N3B—C4B	179.2 (3)	C1Y—C2Y—N3Y—C4Y	179.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N1B	0.88	2.07	2.946 (4)	171
N21A—H21B···O2X	0.88	2.46	3.176 (4)	139
N3A—H3A···O41Bⁱ	0.88	1.89	2.765 (3)	174
N61A—H61A···O2Xⁱⁱ	0.88	2.15	2.939 (4)	150
N61A—H61B···O41Bⁱⁱⁱ	0.88	2.22	2.975 (4)	144
N21B—H21C···N1A	0.88	2.16	3.029 (4)	172
N3B—H3B···O41A^iv	0.88	1.84	2.700 (4)	166
N61B—H61C···O2X	0.88	2.17	2.960 (4)	149
N61B—H61D···O41A^v	0.88	1.95	2.813 (4)	165

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

(Ic) 2,6-diaminopyrimidin-4-one N-methyl-2-pyrrolidone solvate (3/2) top

Crystal data top

C₄H₆N₄O·3/2C₅H₉NO	Z = 4
M_r = 274.83	F(000) = 588
Triclinic, P1	D_x = 1.331 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4550 (9) Å	Cell parameters from 6878 reflections
b = 10.0803 (9) Å	θ = 3.4–25.9°
c = 17.0735 (15) Å	µ = 0.10 mm⁻¹
α = 75.558 (7)°	T = 173 K
β = 78.222 (8)°	Block, colourless
γ = 81.363 (8)°	0.25 × 0.20 × 0.20 mm
V = 1371.9 (2) Å³

Data collection top

Stoe IPDS II two-circle diffractometer	2940 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.091
Graphite monochromator	θ_max = 25.7°, θ_min = 3.3°
ω scans	h = −10→8
18821 measured reflections	k = −12→12
5116 independent reflections	l = −20→20

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0536P)²] where P = (F_o² + 2F_c²)/3
5116 reflections	(Δ/σ)_max < 0.001
355 parameters	Δρ_max = 0.48 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₄H₆N₄O·3/2C₅H₉NO	γ = 81.363 (8)°
M_r = 274.83	V = 1371.9 (2) Å³
Triclinic, P1	Z = 4
a = 8.4550 (9) Å	Mo Kα radiation
b = 10.0803 (9) Å	µ = 0.10 mm⁻¹
c = 17.0735 (15) Å	T = 173 K
α = 75.558 (7)°	0.25 × 0.20 × 0.20 mm
β = 78.222 (8)°

Data collection top

Stoe IPDS II two-circle diffractometer	2940 reflections with I > 2σ(I)
18821 measured reflections	R_int = 0.091
5116 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 0.91	Δρ_max = 0.48 e Å⁻³
5116 reflections	Δρ_min = −0.29 e Å⁻³
355 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
N1A	0.1749 (2)	0.8568 (2)	0.48510 (12)	0.0198 (5)
C2A	0.2934 (3)	0.7826 (2)	0.44640 (14)	0.0188 (5)
N21A	0.3474 (3)	0.8264 (2)	0.36598 (12)	0.0261 (5)
H21A	0.3041	0.9048	0.3387	0.031*
H21B	0.4262	0.7768	0.3404	0.031*
N3A	0.3652 (3)	0.6599 (2)	0.48510 (12)	0.0211 (5)
H3A	0.4439	0.6148	0.4565	0.025*
C4A	0.3175 (3)	0.6034 (3)	0.56900 (15)	0.0214 (6)
O41A	0.3903 (2)	0.49007 (18)	0.59931 (10)	0.0299 (5)
C5A	0.1925 (3)	0.6811 (3)	0.61010 (15)	0.0217 (6)
H5A	0.1534	0.6490	0.6670	0.026*
C6A	0.1254 (3)	0.8057 (3)	0.56730 (14)	0.0196 (6)
N61A	0.0057 (3)	0.8861 (2)	0.60364 (13)	0.0286 (6)
H61A	−0.0339	0.9644	0.5746	0.034*
H61B	−0.0328	0.8604	0.6564	0.034*
N1B	0.8413 (3)	0.4999 (2)	0.09722 (12)	0.0214 (5)
C2B	0.7368 (3)	0.4523 (3)	0.16360 (14)	0.0216 (6)
N21B	0.7296 (3)	0.3163 (2)	0.19107 (13)	0.0284 (6)
H21C	0.7946	0.2586	0.1648	0.034*
H21D	0.6599	0.2847	0.2353	0.034*
N3B	0.6354 (3)	0.5359 (2)	0.20754 (13)	0.0296 (6)
H3B	0.5701	0.4979	0.2520	0.036*
C4B	0.6298 (4)	0.6790 (3)	0.18566 (15)	0.0309 (7)
O41B	0.5284 (3)	0.7464 (2)	0.22870 (12)	0.0513 (7)
C5B	0.7414 (4)	0.7304 (3)	0.11565 (15)	0.0290 (7)
H5B	0.7467	0.8269	0.0967	0.035*
C6B	0.8436 (3)	0.6400 (3)	0.07435 (14)	0.0223 (6)
N61B	0.9542 (3)	0.6831 (2)	0.00733 (14)	0.0336 (6)
H61C	1.0171	0.6228	−0.0177	0.040*
H61D	0.9637	0.7717	−0.0115	0.040*
N1X	−0.4023 (3)	0.8017 (2)	0.86524 (14)	0.0320 (6)
C1X	−0.5096 (4)	0.9227 (3)	0.8771 (2)	0.0413 (8)
H1X1	−0.4797	1.0007	0.8316	0.062*
H1X2	−0.5004	0.9435	0.9290	0.062*
H1X3	−0.6217	0.9064	0.8788	0.062*
C2X	−0.2725 (3)	0.8037 (3)	0.80486 (16)	0.0295 (7)
O2X	−0.2312 (2)	0.9042 (2)	0.74986 (11)	0.0348 (5)
C3X	−0.1808 (4)	0.6596 (3)	0.81699 (18)	0.0366 (7)
H3X1	−0.0782	0.6583	0.8367	0.044*
H3X2	−0.1553	0.6278	0.7650	0.044*
C4X	−0.2959 (4)	0.5697 (3)	0.8809 (2)	0.0468 (9)
H4X1	−0.2363	0.5035	0.9211	0.056*
H4X2	−0.3522	0.5178	0.8547	0.056*
C5X	−0.4181 (4)	0.6705 (3)	0.92335 (17)	0.0344 (7)
H5X1	−0.5300	0.6445	0.9331	0.041*
H5X2	−0.3900	0.6731	0.9764	0.041*
N1Y	0.2529 (3)	0.3622 (3)	0.41759 (15)	0.0362 (6)
C1Y	0.1838 (4)	0.4928 (3)	0.3782 (2)	0.0450 (8)
H1Y1	0.2572	0.5290	0.3274	0.068*
H1Y2	0.1675	0.5565	0.4149	0.068*
H1Y3	0.0790	0.4832	0.3652	0.068*
C2Y	0.3710 (3)	0.2859 (3)	0.37989 (18)	0.0329 (7)
O2Y	0.4378 (2)	0.3217 (2)	0.30683 (11)	0.0385 (5)
C3Y	0.4087 (4)	0.1507 (3)	0.43819 (18)	0.0376 (7)
H3Y1	0.5250	0.1361	0.4432	0.045*
H3Y2	0.3821	0.0729	0.4193	0.045*
C4Y	0.3000 (4)	0.1646 (3)	0.52061 (18)	0.0423 (8)
H4Y1	0.3672	0.1651	0.5617	0.051*
H4Y2	0.2323	0.0870	0.5421	0.051*
C5Y	0.1932 (4)	0.3011 (3)	0.50258 (17)	0.0404 (8)
H5Y1	0.0775	0.2855	0.5106	0.048*
H5Y2	0.2043	0.3610	0.5387	0.048*
N1Z	0.9171 (3)	1.1175 (3)	−0.15175 (17)	0.0447 (7)
C1Z	0.8019 (5)	1.1020 (5)	−0.0758 (2)	0.0622 (11)
H1Z1	0.7925	1.0039	−0.0518	0.093*
H1Z2	0.6956	1.1486	−0.0867	0.093*
H1Z3	0.8392	1.1430	−0.0374	0.093*
C2Z	1.0342 (4)	1.0210 (3)	−0.1650 (2)	0.0403 (8)
O2Z	1.0661 (3)	0.90783 (19)	−0.11935 (12)	0.0362 (5)
C3Z	1.1344 (4)	1.0737 (3)	−0.25077 (19)	0.0453 (8)
H3Z1	1.2449	1.0888	−0.2462	0.054*
H3Z2	1.1436	1.0070	−0.2857	0.054*
C4Z	1.0418 (5)	1.2071 (4)	−0.2859 (2)	0.0623 (11)
H4Z1	0.9908	1.1971	−0.3311	0.075*
H4Z2	1.1149	1.2809	−0.3074	0.075*
C5Z	0.9099 (5)	1.2417 (3)	−0.2140 (2)	0.0508 (10)
H5Z1	0.9357	1.3201	−0.1953	0.061*
H5Z2	0.8013	1.2639	−0.2301	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0181 (11)	0.0213 (11)	0.0183 (10)	0.0032 (9)	−0.0011 (8)	−0.0064 (8)
C2A	0.0211 (13)	0.0168 (13)	0.0190 (12)	−0.0006 (10)	−0.0033 (10)	−0.0062 (10)
N21A	0.0306 (13)	0.0227 (12)	0.0180 (10)	0.0066 (10)	0.0025 (9)	−0.0028 (9)
N3A	0.0211 (11)	0.0208 (11)	0.0193 (10)	0.0052 (9)	−0.0008 (8)	−0.0070 (8)
C4A	0.0224 (14)	0.0206 (13)	0.0224 (12)	−0.0011 (10)	−0.0061 (11)	−0.0063 (10)
O41A	0.0360 (11)	0.0243 (10)	0.0234 (9)	0.0111 (8)	−0.0050 (8)	−0.0030 (8)
C5A	0.0202 (13)	0.0259 (14)	0.0173 (12)	−0.0009 (11)	−0.0010 (10)	−0.0045 (10)
C6A	0.0166 (13)	0.0221 (13)	0.0200 (12)	0.0001 (10)	−0.0018 (10)	−0.0068 (10)
N61A	0.0299 (13)	0.0278 (12)	0.0192 (11)	0.0083 (10)	0.0038 (9)	−0.0021 (9)
N1B	0.0239 (12)	0.0210 (11)	0.0170 (10)	−0.0012 (9)	0.0014 (9)	−0.0048 (8)
C2B	0.0184 (13)	0.0273 (14)	0.0164 (12)	0.0017 (11)	−0.0020 (10)	−0.0034 (10)
N21B	0.0287 (13)	0.0224 (12)	0.0281 (12)	−0.0025 (10)	0.0057 (10)	−0.0033 (9)
N3B	0.0306 (13)	0.0283 (12)	0.0196 (11)	0.0035 (10)	0.0091 (9)	−0.0012 (9)
C4B	0.0370 (17)	0.0295 (15)	0.0191 (13)	0.0094 (13)	−0.0010 (12)	−0.0033 (11)
O41B	0.0666 (16)	0.0360 (12)	0.0299 (11)	0.0207 (11)	0.0186 (11)	−0.0055 (9)
C5B	0.0372 (17)	0.0238 (14)	0.0209 (13)	0.0036 (12)	0.0024 (12)	−0.0057 (11)
C6B	0.0218 (14)	0.0263 (14)	0.0172 (12)	−0.0005 (11)	−0.0011 (10)	−0.0051 (10)
N61B	0.0411 (15)	0.0184 (11)	0.0328 (13)	−0.0028 (10)	0.0137 (11)	−0.0065 (10)
N1X	0.0280 (13)	0.0342 (14)	0.0308 (13)	−0.0012 (11)	−0.0015 (10)	−0.0061 (10)
C1X	0.0308 (17)	0.0410 (18)	0.0509 (19)	0.0003 (14)	−0.0011 (14)	−0.0154 (15)
C2X	0.0237 (15)	0.0446 (18)	0.0235 (14)	−0.0019 (12)	−0.0054 (12)	−0.0137 (13)
O2X	0.0317 (11)	0.0370 (11)	0.0266 (10)	−0.0026 (9)	0.0054 (9)	0.0000 (9)
C3X	0.0334 (17)	0.0405 (17)	0.0353 (16)	0.0064 (13)	−0.0108 (13)	−0.0097 (13)
C4X	0.050 (2)	0.0358 (18)	0.052 (2)	0.0011 (15)	−0.0156 (16)	−0.0027 (15)
C5X	0.0310 (16)	0.0387 (17)	0.0288 (15)	−0.0064 (13)	−0.0066 (12)	0.0039 (12)
N1Y	0.0349 (14)	0.0348 (14)	0.0364 (14)	−0.0067 (11)	−0.0010 (11)	−0.0057 (11)
C1Y	0.0393 (19)	0.0405 (19)	0.057 (2)	−0.0020 (15)	−0.0098 (16)	−0.0152 (15)
C2Y	0.0225 (15)	0.0433 (18)	0.0400 (17)	−0.0134 (13)	−0.0009 (13)	−0.0206 (14)
O2Y	0.0334 (12)	0.0540 (13)	0.0257 (10)	−0.0173 (10)	0.0091 (9)	−0.0086 (9)
C3Y	0.0374 (18)	0.0368 (17)	0.0393 (17)	−0.0135 (13)	−0.0080 (14)	−0.0036 (13)
C4Y	0.0399 (19)	0.049 (2)	0.0341 (16)	−0.0193 (15)	0.0017 (14)	−0.0010 (14)
C5Y	0.0391 (18)	0.059 (2)	0.0270 (15)	−0.0246 (15)	0.0049 (13)	−0.0149 (14)
N1Z	0.0434 (17)	0.0421 (16)	0.0483 (16)	−0.0022 (13)	−0.0110 (13)	−0.0085 (13)
C1Z	0.048 (2)	0.097 (3)	0.0421 (19)	−0.021 (2)	0.0120 (17)	−0.026 (2)
C2Z	0.0429 (19)	0.0347 (18)	0.0505 (19)	−0.0043 (14)	−0.0192 (15)	−0.0137 (15)
O2Z	0.0420 (13)	0.0237 (10)	0.0335 (11)	−0.0015 (9)	0.0025 (9)	0.0026 (8)
C3Z	0.053 (2)	0.050 (2)	0.0326 (16)	−0.0086 (16)	−0.0062 (15)	−0.0074 (14)
C4Z	0.066 (3)	0.064 (3)	0.046 (2)	−0.005 (2)	−0.0079 (19)	0.0057 (18)
C5Z	0.060 (2)	0.0388 (19)	0.050 (2)	0.0135 (17)	−0.0253 (17)	−0.0014 (15)

Geometric parameters (Å, º) top

N1A—C2A	1.323 (3)	C3X—H3X1	0.9900
N1A—C6A	1.369 (3)	C3X—H3X2	0.9900
C2A—N21A	1.338 (3)	C4X—C5X	1.539 (4)
C2A—N3A	1.366 (3)	C4X—H4X1	0.9900
N21A—H21A	0.8800	C4X—H4X2	0.9900
N21A—H21B	0.8800	C5X—H5X1	0.9900
N3A—C4A	1.402 (3)	C5X—H5X2	0.9900
N3A—H3A	0.8800	N1Y—C2Y	1.325 (4)
C4A—O41A	1.255 (3)	N1Y—C1Y	1.420 (4)
C4A—C5A	1.395 (3)	N1Y—C5Y	1.445 (4)
C5A—C6A	1.389 (3)	C1Y—H1Y1	0.9800
C5A—H5A	0.9500	C1Y—H1Y2	0.9800
C6A—N61A	1.347 (3)	C1Y—H1Y3	0.9800
N61A—H61A	0.8800	C2Y—O2Y	1.247 (3)
N61A—H61B	0.8800	C2Y—C3Y	1.507 (4)
N1B—C2B	1.320 (3)	C3Y—C4Y	1.542 (4)
N1B—C6B	1.371 (3)	C3Y—H3Y1	0.9900
C2B—N3B	1.358 (3)	C3Y—H3Y2	0.9900
C2B—N21B	1.340 (3)	C4Y—C5Y	1.527 (5)
N21B—H21C	0.8800	C4Y—H4Y1	0.9900
N21B—H21D	0.8800	C4Y—H4Y2	0.9900
N3B—C4B	1.392 (4)	C5Y—H5Y1	0.9900
N3B—H3B	0.8800	C5Y—H5Y2	0.9900
C4B—O41B	1.247 (3)	N1Z—C2Z	1.307 (4)
C4B—C5B	1.402 (4)	N1Z—C5Z	1.428 (4)
C5B—C6B	1.381 (4)	N1Z—C1Z	1.443 (4)
C5B—H5B	0.9500	C1Z—H1Z1	0.9800
C6B—N61B	1.345 (3)	C1Z—H1Z2	0.9800
N61B—H61C	0.8800	C1Z—H1Z3	0.9800
N61B—H61D	0.8800	C2Z—O2Z	1.238 (3)
N1X—C2X	1.342 (4)	C2Z—C3Z	1.544 (5)
N1X—C1X	1.438 (4)	C3Z—C4Z	1.501 (5)
N1X—C5X	1.448 (4)	C3Z—H3Z1	0.9900
C1X—H1X1	0.9800	C3Z—H3Z2	0.9900
C1X—H1X2	0.9800	C4Z—C5Z	1.552 (5)
C1X—H1X3	0.9800	C4Z—H4Z1	0.9900
C2X—O2X	1.236 (3)	C4Z—H4Z2	0.9900
C2X—C3X	1.527 (4)	C5Z—H5Z1	0.9900
C3X—C4X	1.516 (5)	C5Z—H5Z2	0.9900

C2A—N1A—C6A	117.09 (19)	H4X1—C4X—H4X2	108.8
N1A—C2A—N21A	120.2 (2)	N1X—C5X—C4X	103.5 (2)
N1A—C2A—N3A	122.7 (2)	N1X—C5X—H5X1	111.1
N21A—C2A—N3A	117.1 (2)	C4X—C5X—H5X1	111.1
C2A—N21A—H21A	120.0	N1X—C5X—H5X2	111.1
C2A—N21A—H21B	120.0	C4X—C5X—H5X2	111.1
H21A—N21A—H21B	120.0	H5X1—C5X—H5X2	109.0
C2A—N3A—C4A	122.0 (2)	C2Y—N1Y—C1Y	123.6 (3)
C2A—N3A—H3A	119.0	C2Y—N1Y—C5Y	115.2 (3)
C4A—N3A—H3A	119.0	C1Y—N1Y—C5Y	121.1 (3)
O41A—C4A—C5A	126.9 (2)	N1Y—C1Y—H1Y1	109.5
O41A—C4A—N3A	117.6 (2)	N1Y—C1Y—H1Y2	109.5
C5A—C4A—N3A	115.5 (2)	H1Y1—C1Y—H1Y2	109.5
C6A—C5A—C4A	119.6 (2)	N1Y—C1Y—H1Y3	109.5
C6A—C5A—H5A	120.2	H1Y1—C1Y—H1Y3	109.5
C4A—C5A—H5A	120.2	H1Y2—C1Y—H1Y3	109.5
N1A—C6A—N61A	114.5 (2)	O2Y—C2Y—N1Y	124.3 (3)
N1A—C6A—C5A	123.0 (2)	O2Y—C2Y—C3Y	126.0 (3)
N61A—C6A—C5A	122.5 (2)	N1Y—C2Y—C3Y	109.7 (3)
C6A—N61A—H61A	120.0	C2Y—C3Y—C4Y	104.3 (2)
C6A—N61A—H61B	120.0	C2Y—C3Y—H3Y1	110.9
H61A—N61A—H61B	120.0	C4Y—C3Y—H3Y1	110.9
C2B—N1B—C6B	116.4 (2)	C2Y—C3Y—H3Y2	110.9
N1B—C2B—N3B	122.7 (2)	C4Y—C3Y—H3Y2	110.9
N1B—C2B—N21B	120.1 (2)	H3Y1—C3Y—H3Y2	108.9
N3B—C2B—N21B	117.2 (2)	C3Y—C4Y—C5Y	106.1 (2)
C2B—N21B—H21C	120.0	C3Y—C4Y—H4Y1	110.5
C2B—N21B—H21D	120.0	C5Y—C4Y—H4Y1	110.5
H21C—N21B—H21D	120.0	C3Y—C4Y—H4Y2	110.5
C2B—N3B—C4B	123.1 (2)	C5Y—C4Y—H4Y2	110.5
C2B—N3B—H3B	118.4	H4Y1—C4Y—H4Y2	108.7
C4B—N3B—H3B	118.4	N1Y—C5Y—C4Y	104.4 (2)
O41B—C4B—C5B	127.4 (3)	N1Y—C5Y—H5Y1	110.9
O41B—C4B—N3B	118.0 (2)	C4Y—C5Y—H5Y1	110.9
C5B—C4B—N3B	114.6 (2)	N1Y—C5Y—H5Y2	110.9
C6B—C5B—C4B	119.6 (2)	C4Y—C5Y—H5Y2	110.9
C6B—C5B—H5B	120.2	H5Y1—C5Y—H5Y2	108.9
C4B—C5B—H5B	120.2	C2Z—N1Z—C5Z	117.7 (3)
N61B—C6B—N1B	114.1 (2)	C2Z—N1Z—C1Z	121.5 (3)
N61B—C6B—C5B	122.4 (2)	C5Z—N1Z—C1Z	120.8 (3)
N1B—C6B—C5B	123.5 (2)	N1Z—C1Z—H1Z1	109.5
C6B—N61B—H61C	120.0	N1Z—C1Z—H1Z2	109.5
C6B—N61B—H61D	120.0	H1Z1—C1Z—H1Z2	109.5
H61C—N61B—H61D	120.0	N1Z—C1Z—H1Z3	109.5
C2X—N1X—C1X	123.2 (2)	H1Z1—C1Z—H1Z3	109.5
C2X—N1X—C5X	114.9 (2)	H1Z2—C1Z—H1Z3	109.5
C1X—N1X—C5X	121.6 (2)	O2Z—C2Z—N1Z	128.7 (3)
N1X—C1X—H1X1	109.5	O2Z—C2Z—C3Z	124.0 (3)
N1X—C1X—H1X2	109.5	N1Z—C2Z—C3Z	107.3 (3)
H1X1—C1X—H1X2	109.5	C4Z—C3Z—C2Z	104.9 (3)
N1X—C1X—H1X3	109.5	C4Z—C3Z—H3Z1	110.8
H1X1—C1X—H1X3	109.5	C2Z—C3Z—H3Z1	110.8
H1X2—C1X—H1X3	109.5	C4Z—C3Z—H3Z2	110.8
O2X—C2X—N1X	126.6 (3)	C2Z—C3Z—H3Z2	110.8
O2X—C2X—C3X	125.5 (2)	H3Z1—C3Z—H3Z2	108.8
N1X—C2X—C3X	107.9 (2)	C3Z—C4Z—C5Z	105.9 (3)
C2X—C3X—C4X	104.6 (2)	C3Z—C4Z—H4Z1	110.6
C2X—C3X—H3X1	110.8	C5Z—C4Z—H4Z1	110.6
C4X—C3X—H3X1	110.8	C3Z—C4Z—H4Z2	110.6
C2X—C3X—H3X2	110.8	C5Z—C4Z—H4Z2	110.6
C4X—C3X—H3X2	110.8	H4Z1—C4Z—H4Z2	108.7
H3X1—C3X—H3X2	108.9	N1Z—C5Z—C4Z	102.9 (3)
C3X—C4X—C5X	105.1 (3)	N1Z—C5Z—H5Z1	111.2
C3X—C4X—H4X1	110.7	C4Z—C5Z—H5Z1	111.2
C5X—C4X—H4X1	110.7	N1Z—C5Z—H5Z2	111.2
C3X—C4X—H4X2	110.7	C4Z—C5Z—H5Z2	111.2
C5X—C4X—H4X2	110.7	H5Z1—C5Z—H5Z2	109.1

C6A—N1A—C2A—N21A	179.8 (2)	C5X—N1X—C2X—C3X	0.8 (4)
C6A—N1A—C2A—N3A	0.1 (4)	O2X—C2X—C3X—C4X	−169.5 (3)
N1A—C2A—N3A—C4A	0.3 (4)	N1X—C2X—C3X—C4X	11.9 (3)
N21A—C2A—N3A—C4A	−179.4 (3)	C2X—C3X—C4X—C5X	−19.0 (3)
C2A—N3A—C4A—O41A	180.0 (3)	C2X—N1X—C5X—C4X	−12.9 (4)
C2A—N3A—C4A—C5A	−0.2 (4)	C1X—N1X—C5X—C4X	172.9 (3)
O41A—C4A—C5A—C6A	179.5 (3)	C3X—C4X—C5X—N1X	19.3 (3)
N3A—C4A—C5A—C6A	−0.3 (4)	C1Y—N1Y—C2Y—O2Y	2.3 (5)
C2A—N1A—C6A—N61A	179.4 (3)	C5Y—N1Y—C2Y—O2Y	−179.8 (3)
C2A—N1A—C6A—C5A	−0.6 (4)	C1Y—N1Y—C2Y—C3Y	−176.9 (3)
C4A—C5A—C6A—N1A	0.8 (4)	C5Y—N1Y—C2Y—C3Y	1.1 (4)
C4A—C5A—C6A—N61A	−179.3 (3)	O2Y—C2Y—C3Y—C4Y	176.5 (3)
C6B—N1B—C2B—N3B	0.3 (4)	N1Y—C2Y—C3Y—C4Y	−4.4 (4)
C6B—N1B—C2B—N21B	−178.5 (2)	C2Y—C3Y—C4Y—C5Y	5.8 (3)
N1B—C2B—N3B—C4B	1.5 (4)	C2Y—N1Y—C5Y—C4Y	2.7 (4)
N21B—C2B—N3B—C4B	−179.7 (3)	C1Y—N1Y—C5Y—C4Y	−179.3 (3)
C2B—N3B—C4B—O41B	177.6 (3)	C3Y—C4Y—C5Y—N1Y	−5.2 (3)
C2B—N3B—C4B—C5B	−1.9 (4)	C5Z—N1Z—C2Z—O2Z	177.9 (3)
O41B—C4B—C5B—C6B	−178.8 (3)	C1Z—N1Z—C2Z—O2Z	0.1 (6)
N3B—C4B—C5B—C6B	0.7 (4)	C5Z—N1Z—C2Z—C3Z	−1.0 (4)
C2B—N1B—C6B—N61B	178.7 (3)	C1Z—N1Z—C2Z—C3Z	−178.9 (3)
C2B—N1B—C6B—C5B	−1.6 (4)	O2Z—C2Z—C3Z—C4Z	174.6 (3)
C4B—C5B—C6B—N61B	−179.3 (3)	N1Z—C2Z—C3Z—C4Z	−6.4 (4)
C4B—C5B—C6B—N1B	1.0 (4)	C2Z—C3Z—C4Z—C5Z	10.5 (4)
C1X—N1X—C2X—O2X	−3.8 (5)	C2Z—N1Z—C5Z—C4Z	7.7 (4)
C5X—N1X—C2X—O2X	−177.8 (3)	C1Z—N1Z—C5Z—C4Z	−174.5 (3)
C1X—N1X—C2X—C3X	174.8 (3)	C3Z—C4Z—C5Z—N1Z	−10.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···O2Xⁱ	0.88	2.22	3.092 (3)	169
N21A—H21B···O41B	0.88	2.00	2.756 (3)	143
N3A—H3A···O41Aⁱⁱ	0.88	1.87	2.750 (3)	177
N61A—H61A···N1Aⁱ	0.88	2.15	3.023 (3)	169
N61A—H61B···O2X	0.88	2.14	2.891 (3)	142
N21B—H21C···O2Zⁱⁱⁱ	0.88	2.12	2.989 (3)	170
N21B—H21D···O2Y	0.88	2.06	2.832 (3)	146
N3B—H3B···O2Y	0.88	2.15	2.904 (3)	143
N61B—H61C···N1Bⁱⁱⁱ	0.88	2.13	3.001 (3)	170
N61B—H61D···O2Z	0.88	2.11	2.840 (3)	139

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

(IIa) 2-amino-6-methylpyrimidin-4(3H)-one–2-amino-6-methylpyrimidin-4(1H)-one–dimethylacetamide (1/1/1) top

Crystal data top

C₅H₇N₃O·C₅H₇N₃O·C₄H₉NO	Z = 2
M_r = 337.39	F(000) = 360
Triclinic, P1	D_x = 1.306 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8763 (13) Å	Cell parameters from 2325 reflections
b = 9.6078 (17) Å	θ = 3.4–25.9°
c = 12.3115 (19) Å	µ = 0.10 mm⁻¹
α = 108.780 (13)°	T = 173 K
β = 95.194 (13)°	Block, colourless
γ = 99.959 (13)°	0.40 × 0.25 × 0.10 mm
V = 858.0 (2) Å³

Data collection top

Stoe IPDS II two-circle diffractometer	1427 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.131
Graphite monochromator	θ_max = 25.6°, θ_min = 3.4°
ω scans	h = −9→9
7199 measured reflections	k = −11→11
3208 independent reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.204	w = 1/[σ²(F_o²) + (0.1094P)²] where P = (F_o² + 2F_c²)/3
S = 0.82	(Δ/σ)_max < 0.001
3208 reflections	Δρ_max = 0.45 e Å⁻³
223 parameters	Δρ_min = −0.47 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.018 (6)

Crystal data top

C₅H₇N₃O·C₅H₇N₃O·C₄H₉NO	γ = 99.959 (13)°
M_r = 337.39	V = 858.0 (2) Å³
Triclinic, P1	Z = 2
a = 7.8763 (13) Å	Mo Kα radiation
b = 9.6078 (17) Å	µ = 0.10 mm⁻¹
c = 12.3115 (19) Å	T = 173 K
α = 108.780 (13)°	0.40 × 0.25 × 0.10 mm
β = 95.194 (13)°

Data collection top

Stoe IPDS II two-circle diffractometer	1427 reflections with I > 2σ(I)
7199 measured reflections	R_int = 0.131
3208 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.204	H-atom parameters constrained
S = 0.82	Δρ_max = 0.45 e Å⁻³
3208 reflections	Δρ_min = −0.47 e Å⁻³
223 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
N1A	0.1822 (4)	0.6323 (4)	0.4673 (3)	0.0313 (8)
H1A	0.1566	0.6699	0.5375	0.038*
C2A	0.2487 (5)	0.5060 (4)	0.4397 (3)	0.0297 (9)
N21A	0.2741 (4)	0.4471 (4)	0.5222 (3)	0.0398 (9)
H21A	0.3160	0.3649	0.5073	0.048*
H21B	0.2491	0.4903	0.5918	0.048*
N3A	0.2863 (4)	0.4411 (4)	0.3346 (3)	0.0295 (8)
C4A	0.2594 (5)	0.5053 (4)	0.2508 (3)	0.0264 (8)
O41A	0.2933 (4)	0.4439 (3)	0.1509 (2)	0.0359 (7)
C5A	0.1922 (5)	0.6414 (5)	0.2810 (3)	0.0350 (10)
H5A	0.1748	0.6880	0.2248	0.042*
C6A	0.1541 (5)	0.7026 (4)	0.3887 (3)	0.0317 (9)
C61A	0.0839 (6)	0.8407 (5)	0.4293 (4)	0.0438 (11)
H61A	0.1733	0.9216	0.4860	0.066*
H61B	−0.0189	0.8208	0.4658	0.066*
H61C	0.0507	0.8710	0.3630	0.066*
N1B	0.5073 (4)	−0.0211 (3)	0.1427 (2)	0.0274 (7)
C2B	0.4440 (4)	0.1017 (4)	0.1717 (3)	0.0241 (8)
N21B	0.4036 (4)	0.1620 (4)	0.0915 (2)	0.0308 (8)
H21C	0.4194	0.1196	0.0194	0.037*
H21D	0.3613	0.2441	0.1108	0.037*
N3B	0.4118 (4)	0.1701 (4)	0.2808 (2)	0.0254 (7)
H3B	0.3701	0.2524	0.2947	0.030*
C4B	0.4413 (5)	0.1168 (5)	0.3705 (3)	0.0306 (9)
O41B	0.4064 (4)	0.1843 (3)	0.4680 (2)	0.0408 (8)
C5B	0.5096 (5)	−0.0174 (4)	0.3406 (3)	0.0303 (9)
H5B	0.5334	−0.0625	0.3970	0.036*
C6B	0.5399 (5)	−0.0791 (4)	0.2293 (3)	0.0282 (9)
C61B	0.6104 (6)	−0.2198 (5)	0.1948 (3)	0.0381 (10)
H61D	0.5181	−0.3044	0.1449	0.057*
H61E	0.6512	−0.2403	0.2646	0.057*
H61F	0.7079	−0.2065	0.1524	0.057*
C1X	0.0469 (6)	0.8732 (5)	0.8135 (4)	0.0471 (12)
H1X1	0.0320	0.8923	0.7401	0.071*
H1X2	0.1235	0.9611	0.8731	0.071*
H1X3	−0.0672	0.8541	0.8382	0.071*
C2X	0.1269 (5)	0.7381 (5)	0.7971 (3)	0.0367 (10)
O2X	0.1735 (4)	0.6728 (4)	0.7028 (2)	0.0436 (8)
N3X	0.1524 (5)	0.6883 (4)	0.8854 (3)	0.0418 (9)
C4X	0.2320 (7)	0.5590 (6)	0.8719 (5)	0.0606 (15)
H4X1	0.1507	0.4677	0.8198	0.091*
H4X2	0.2593	0.5489	0.9479	0.091*
H4X3	0.3397	0.5734	0.8389	0.091*
C5X	0.0938 (7)	0.7573 (7)	0.9971 (4)	0.0661 (17)
H5X1	0.0295	0.8337	0.9909	0.099*
H5X2	0.1956	0.8045	1.0583	0.099*
H5X3	0.0176	0.6795	1.0164	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0372 (18)	0.0277 (18)	0.0274 (17)	0.0105 (15)	0.0101 (13)	0.0040 (14)
C2A	0.031 (2)	0.027 (2)	0.029 (2)	0.0074 (17)	0.0035 (15)	0.0065 (16)
N21A	0.052 (2)	0.046 (2)	0.0283 (17)	0.0251 (18)	0.0163 (15)	0.0130 (16)
N3A	0.0329 (18)	0.0283 (18)	0.0286 (16)	0.0097 (14)	0.0104 (13)	0.0085 (14)
C4A	0.0276 (19)	0.024 (2)	0.0287 (19)	0.0080 (16)	0.0048 (15)	0.0090 (16)
O41A	0.0500 (17)	0.0338 (16)	0.0282 (14)	0.0157 (14)	0.0112 (12)	0.0116 (12)
C5A	0.035 (2)	0.034 (2)	0.039 (2)	0.0115 (19)	0.0043 (17)	0.0137 (19)
C6A	0.029 (2)	0.024 (2)	0.037 (2)	0.0049 (17)	0.0028 (16)	0.0039 (17)
C61A	0.054 (3)	0.030 (2)	0.048 (2)	0.016 (2)	0.012 (2)	0.0084 (19)
N1B	0.0366 (18)	0.0255 (17)	0.0229 (15)	0.0111 (15)	0.0067 (12)	0.0093 (13)
C2B	0.0245 (19)	0.028 (2)	0.0184 (17)	0.0063 (17)	0.0054 (14)	0.0050 (16)
N21B	0.0427 (19)	0.0327 (19)	0.0245 (16)	0.0207 (15)	0.0118 (13)	0.0117 (14)
N3B	0.0317 (17)	0.0254 (17)	0.0233 (15)	0.0121 (14)	0.0080 (12)	0.0100 (13)
C4B	0.039 (2)	0.031 (2)	0.0233 (19)	0.0091 (18)	0.0061 (15)	0.0109 (16)
O41B	0.068 (2)	0.0397 (17)	0.0234 (13)	0.0267 (15)	0.0155 (12)	0.0122 (12)
C5B	0.041 (2)	0.030 (2)	0.0268 (19)	0.0142 (18)	0.0080 (16)	0.0150 (17)
C6B	0.0297 (19)	0.024 (2)	0.0323 (19)	0.0080 (16)	0.0048 (15)	0.0100 (16)
C61B	0.048 (2)	0.036 (2)	0.038 (2)	0.019 (2)	0.0131 (18)	0.0168 (19)
C1X	0.040 (2)	0.034 (2)	0.061 (3)	0.011 (2)	0.012 (2)	0.005 (2)
C2X	0.030 (2)	0.039 (3)	0.038 (2)	0.0034 (19)	0.0078 (17)	0.0108 (19)
O2X	0.0459 (17)	0.0487 (19)	0.0328 (15)	0.0125 (14)	0.0173 (12)	0.0053 (13)
N3X	0.041 (2)	0.046 (2)	0.0386 (19)	0.0078 (18)	0.0066 (15)	0.0158 (17)
C4X	0.055 (3)	0.057 (3)	0.071 (3)	0.002 (3)	−0.010 (3)	0.034 (3)
C5X	0.061 (3)	0.093 (5)	0.032 (2)	−0.007 (3)	0.007 (2)	0.016 (3)

Geometric parameters (Å, º) top

N1A—C2A	1.360 (5)	N3B—H3B	0.8800
N1A—C6A	1.370 (5)	C4B—O41B	1.247 (4)
N1A—H1A	0.8800	C4B—C5B	1.435 (5)
C2A—N3A	1.329 (5)	C5B—C6B	1.368 (5)
C2A—N21A	1.328 (5)	C5B—H5B	0.9500
N21A—H21A	0.8800	C6B—C61B	1.499 (5)
N21A—H21B	0.8800	C61B—H61D	0.9800
N3A—C4A	1.380 (5)	C61B—H61E	0.9800
C4A—O41A	1.256 (4)	C61B—H61F	0.9800
C4A—C5A	1.446 (5)	C1X—C2X	1.503 (6)
C5A—C6A	1.351 (5)	C1X—H1X1	0.9800
C5A—H5A	0.9500	C1X—H1X2	0.9800
C6A—C61A	1.481 (6)	C1X—H1X3	0.9800
C61A—H61A	0.9800	C2X—O2X	1.250 (5)
C61A—H61B	0.9800	C2X—N3X	1.334 (5)
C61A—H61C	0.9800	N3X—C4X	1.456 (6)
N1B—C2B	1.317 (5)	N3X—C5X	1.476 (6)
N1B—C6B	1.377 (5)	C4X—H4X1	0.9800
C2B—N21B	1.336 (4)	C4X—H4X2	0.9800
C2B—N3B	1.361 (4)	C4X—H4X3	0.9800
N21B—H21C	0.8800	C5X—H5X1	0.9800
N21B—H21D	0.8800	C5X—H5X2	0.9800
N3B—C4B	1.377 (5)	C5X—H5X3	0.9800

C2A—N1A—C6A	121.7 (3)	N3B—C4B—C5B	114.9 (3)
C2A—N1A—H1A	119.1	C6B—C5B—C4B	118.6 (4)
C6A—N1A—H1A	119.1	C6B—C5B—H5B	120.7
N3A—C2A—N21A	120.2 (4)	C4B—C5B—H5B	120.7
N3A—C2A—N1A	122.4 (4)	N1B—C6B—C5B	124.1 (4)
N21A—C2A—N1A	117.4 (3)	N1B—C6B—C61B	115.8 (3)
C2A—N21A—H21A	120.0	C5B—C6B—C61B	120.1 (4)
C2A—N21A—H21B	120.0	C6B—C61B—H61D	109.5
H21A—N21A—H21B	120.0	C6B—C61B—H61E	109.5
C2A—N3A—C4A	118.9 (3)	H61D—C61B—H61E	109.5
O41A—C4A—N3A	119.3 (3)	C6B—C61B—H61F	109.5
O41A—C4A—C5A	122.1 (4)	H61D—C61B—H61F	109.5
N3A—C4A—C5A	118.7 (3)	H61E—C61B—H61F	109.5
C6A—C5A—C4A	120.4 (4)	C2X—C1X—H1X1	109.5
C6A—C5A—H5A	119.8	C2X—C1X—H1X2	109.5
C4A—C5A—H5A	119.8	H1X1—C1X—H1X2	109.5
C5A—C6A—N1A	117.9 (4)	C2X—C1X—H1X3	109.5
C5A—C6A—C61A	125.2 (4)	H1X1—C1X—H1X3	109.5
N1A—C6A—C61A	116.9 (3)	H1X2—C1X—H1X3	109.5
C6A—C61A—H61A	109.5	O2X—C2X—N3X	119.1 (4)
C6A—C61A—H61B	109.5	O2X—C2X—C1X	121.4 (4)
H61A—C61A—H61B	109.5	N3X—C2X—C1X	119.5 (4)
C6A—C61A—H61C	109.5	C2X—N3X—C4X	120.5 (4)
H61A—C61A—H61C	109.5	C2X—N3X—C5X	121.4 (4)
H61B—C61A—H61C	109.5	C4X—N3X—C5X	118.1 (4)
C2B—N1B—C6B	116.4 (3)	N3X—C4X—H4X1	109.5
N1B—C2B—N21B	119.9 (3)	N3X—C4X—H4X2	109.5
N1B—C2B—N3B	122.9 (3)	H4X1—C4X—H4X2	109.5
N21B—C2B—N3B	117.1 (3)	N3X—C4X—H4X3	109.5
C2B—N21B—H21C	120.0	H4X1—C4X—H4X3	109.5
C2B—N21B—H21D	120.0	H4X2—C4X—H4X3	109.5
H21C—N21B—H21D	120.0	N3X—C5X—H5X1	109.5
C2B—N3B—C4B	123.1 (3)	N3X—C5X—H5X2	109.5
C2B—N3B—H3B	118.4	H5X1—C5X—H5X2	109.5
C4B—N3B—H3B	118.4	N3X—C5X—H5X3	109.5
O41B—C4B—N3B	119.6 (4)	H5X1—C5X—H5X3	109.5
O41B—C4B—C5B	125.5 (4)	H5X2—C5X—H5X3	109.5

C6A—N1A—C2A—N3A	−1.7 (6)	N1B—C2B—N3B—C4B	−0.4 (5)
C6A—N1A—C2A—N21A	178.9 (3)	N21B—C2B—N3B—C4B	177.6 (3)
N21A—C2A—N3A—C4A	−179.7 (3)	C2B—N3B—C4B—O41B	−179.0 (4)
N1A—C2A—N3A—C4A	1.0 (5)	C2B—N3B—C4B—C5B	0.1 (5)
C2A—N3A—C4A—O41A	−179.4 (4)	O41B—C4B—C5B—C6B	179.4 (4)
C2A—N3A—C4A—C5A	0.4 (5)	N3B—C4B—C5B—C6B	0.3 (5)
O41A—C4A—C5A—C6A	178.7 (4)	C2B—N1B—C6B—C5B	0.3 (5)
N3A—C4A—C5A—C6A	−1.1 (5)	C2B—N1B—C6B—C61B	179.5 (3)
C4A—C5A—C6A—N1A	0.4 (5)	C4B—C5B—C6B—N1B	−0.6 (6)
C4A—C5A—C6A—C61A	−179.6 (4)	C4B—C5B—C6B—C61B	−179.7 (4)
C2A—N1A—C6A—C5A	0.9 (5)	O2X—C2X—N3X—C4X	−0.5 (6)
C2A—N1A—C6A—C61A	−179.0 (4)	C1X—C2X—N3X—C4X	−179.1 (4)
C6B—N1B—C2B—N21B	−177.8 (3)	O2X—C2X—N3X—C5X	−177.6 (4)
C6B—N1B—C2B—N3B	0.2 (5)	C1X—C2X—N3X—C5X	3.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···O41B	0.88	1.92	2.803 (4)	178
N21A—H21B···O2X	0.88	2.06	2.843 (4)	147
N1A—H1A···O2X	0.88	2.02	2.807 (4)	149
N3B—H3B···N3A	0.88	1.97	2.844 (4)	177
N21B—H21C···N1Bⁱ	0.88	2.10	2.969 (4)	172
N21B—H21D···O41A	0.88	2.00	2.877 (4)	173

Symmetry code: (i) −x+1, −y, −z.

(IIb) 2-amino-6-methylpyrimidin-4(3H)-one–2-amino-6-methylpyrimidin-4(1H)-one–N-methyl-2-pyrrolidone (1/1/1) top

Crystal data top

C₅H₇N₃O·C₅H₇N₃O·C₅H9NO	Z = 2
M_r = 349.40	F(000) = 372
Triclinic, P1	D_x = 1.324 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.3321 (7) Å	Cell parameters from 4837 reflections
b = 9.8805 (9) Å	θ = 2.4–25.9°
c = 12.5860 (12) Å	µ = 0.10 mm⁻¹
α = 102.835 (7)°	T = 173 K
β = 98.830 (8)°	Block, colourless
γ = 91.555 (8)°	0.45 × 0.35 × 0.25 mm
V = 876.70 (14) Å³

Data collection top

Stoe IPDS II two-circle diffractometer	1883 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.149
Graphite monochromator	θ_max = 25.6°, θ_min = 3.4°
ω scans	h = −8→8
13229 measured reflections	k = −12→11
3267 independent reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.068	H-atom parameters constrained
wR(F²) = 0.176	w = 1/[σ²(F_o²) + (0.1156P)²] where P = (F_o² + 2F_c²)/3
S = 0.82	(Δ/σ)_max < 0.001
3267 reflections	Δρ_max = 0.34 e Å⁻³
242 parameters	Δρ_min = −0.35 e Å⁻³
16 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.136 (17)

Crystal data top

C₅H₇N₃O·C₅H₇N₃O·C₅H9NO	γ = 91.555 (8)°
M_r = 349.40	V = 876.70 (14) Å³
Triclinic, P1	Z = 2
a = 7.3321 (7) Å	Mo Kα radiation
b = 9.8805 (9) Å	µ = 0.10 mm⁻¹
c = 12.5860 (12) Å	T = 173 K
α = 102.835 (7)°	0.45 × 0.35 × 0.25 mm
β = 98.830 (8)°

Data collection top

Stoe IPDS II two-circle diffractometer	1883 reflections with I > 2σ(I)
13229 measured reflections	R_int = 0.149
3267 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	16 restraints
wR(F²) = 0.176	H-atom parameters constrained
S = 0.82	Δρ_max = 0.34 e Å⁻³
3267 reflections	Δρ_min = −0.35 e Å⁻³
242 parameters

Special details top

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1A	0.8058 (3)	0.3882 (2)	0.55332 (19)	0.0376 (6)
H1A	0.8291	0.3555	0.4862	0.045*
C2A	0.7408 (4)	0.5164 (3)	0.5792 (2)	0.0327 (6)
N21A	0.7152 (4)	0.5868 (2)	0.49943 (18)	0.0408 (6)
H21A	0.6745	0.6709	0.5131	0.049*
H21B	0.7391	0.5491	0.4332	0.049*
N3A	0.7048 (3)	0.5734 (2)	0.67908 (17)	0.0326 (6)
C4A	0.7343 (4)	0.4989 (3)	0.7608 (2)	0.0341 (7)
O41A	0.7026 (3)	0.5522 (2)	0.85511 (15)	0.0424 (6)
C5A	0.8032 (4)	0.3617 (3)	0.7333 (2)	0.0394 (7)
H5A	0.8254	0.3092	0.7883	0.047*
C6A	0.8360 (4)	0.3078 (3)	0.6304 (2)	0.0383 (7)
C61A	0.9049 (5)	0.1678 (3)	0.5920 (3)	0.0504 (9)
H61A	0.9378	0.1255	0.6552	0.076*
H61B	1.0142	0.1772	0.5575	0.076*
H61C	0.8080	0.1088	0.5380	0.076*
N1B	0.4878 (3)	1.0314 (2)	0.86287 (16)	0.0292 (5)
C2B	0.5426 (3)	0.9037 (3)	0.83649 (19)	0.0271 (6)
N21B	0.5804 (3)	0.8304 (2)	0.91387 (16)	0.0334 (6)
H21C	0.5688	0.8672	0.9827	0.040*
H21D	0.6168	0.7454	0.8959	0.040*
N3B	0.5646 (3)	0.8408 (2)	0.73180 (16)	0.0294 (5)
H3B	0.5985	0.7547	0.7187	0.035*
C4B	0.5356 (4)	0.9074 (3)	0.6450 (2)	0.0338 (7)
O41B	0.5629 (4)	0.8447 (2)	0.55216 (14)	0.0504 (7)
C5B	0.4729 (4)	1.0435 (3)	0.6727 (2)	0.0364 (7)
H5B	0.4459	1.0952	0.6175	0.044*
C6B	0.4517 (4)	1.0993 (3)	0.7788 (2)	0.0307 (6)
C61B	0.3855 (5)	1.2424 (3)	0.8115 (2)	0.0416 (7)
H61D	0.3604	1.2820	0.7463	0.062*
H61E	0.4809	1.3016	0.8666	0.062*
H61F	0.2720	1.2374	0.8430	0.062*
C1X	0.7899 (5)	0.4190 (4)	0.1193 (3)	0.0623 (10)
H1XA	0.7901	0.4092	0.0401	0.093*	0.778 (6)
H1XB	0.8702	0.5004	0.1611	0.093*	0.778 (6)
H1XC	0.6636	0.4311	0.1347	0.093*	0.778 (6)
H3XC	0.6551	0.4249	0.0986	0.075*	0.222 (6)
H3XD	0.8535	0.5125	0.1335	0.075*	0.222 (6)
O2X	0.8257 (3)	0.3738 (2)	0.33072 (16)	0.0499 (6)
C3X	0.9511 (5)	0.1439 (3)	0.2625 (3)	0.0521 (9)
H3XA	1.0749	0.1577	0.3090	0.063*	0.778 (6)
H3XB	0.8684	0.0876	0.2936	0.063*	0.778 (6)
H1XD	0.9920	0.0543	0.2261	0.078*	0.222 (6)
H1XE	0.8430	0.1281	0.2964	0.078*	0.222 (6)
H1XF	1.0513	0.1935	0.3198	0.078*	0.222 (6)
C5X	0.9164 (5)	0.1836 (4)	0.0748 (3)	0.0557 (10)
H5XA	1.0270	0.2120	0.0468	0.067*	0.778 (6)
H5XB	0.8174	0.1459	0.0112	0.067*	0.778 (6)
H5XC	0.8270	0.1050	0.0354	0.067*	0.222 (6)
H5XD	1.0425	0.1583	0.0626	0.067*	0.222 (6)
N1X	0.8546 (5)	0.3012 (4)	0.1504 (2)	0.0434 (11)	0.778 (6)
C2X	0.8683 (5)	0.2880 (4)	0.2534 (3)	0.0343 (10)	0.778 (6)
C4X	0.9623 (6)	0.0757 (4)	0.1432 (4)	0.0513 (14)	0.778 (6)
H4XA	1.0882	0.0446	0.1369	0.062*	0.778 (6)
H4XB	0.8730	−0.0063	0.1165	0.062*	0.778 (6)
N1X'	0.9069 (16)	0.2184 (11)	0.1895 (8)	0.040 (4)*	0.222 (6)
C2X'	0.841 (3)	0.3440 (16)	0.2253 (11)	0.058 (6)*	0.222 (6)
C4X'	0.866 (3)	0.3160 (15)	0.0363 (13)	0.071 (6)*	0.222 (6)
H4XC	0.9786	0.3589	0.0189	0.086*	0.222 (6)
H4XD	0.7746	0.2912	−0.0324	0.086*	0.222 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0438 (15)	0.0331 (13)	0.0325 (12)	0.0033 (11)	0.0099 (10)	−0.0026 (10)
C2A	0.0328 (15)	0.0280 (13)	0.0339 (14)	−0.0003 (11)	0.0075 (11)	−0.0015 (11)
N21A	0.0582 (17)	0.0379 (14)	0.0263 (12)	0.0115 (12)	0.0134 (11)	0.0024 (10)
N3A	0.0387 (14)	0.0308 (12)	0.0283 (12)	0.0053 (10)	0.0094 (10)	0.0035 (9)
C4A	0.0366 (16)	0.0321 (15)	0.0327 (14)	0.0027 (12)	0.0094 (12)	0.0028 (11)
O41A	0.0589 (14)	0.0392 (12)	0.0317 (10)	0.0116 (10)	0.0147 (9)	0.0072 (8)
C5A	0.0457 (17)	0.0332 (15)	0.0393 (15)	0.0064 (13)	0.0061 (13)	0.0083 (12)
C6A	0.0415 (17)	0.0303 (14)	0.0398 (16)	0.0033 (12)	0.0073 (13)	0.0008 (12)
C61A	0.061 (2)	0.0361 (17)	0.0511 (19)	0.0146 (15)	0.0098 (16)	0.0010 (14)
N1B	0.0360 (13)	0.0276 (12)	0.0229 (10)	0.0039 (10)	0.0041 (9)	0.0037 (8)
C2B	0.0268 (14)	0.0328 (14)	0.0202 (12)	0.0010 (11)	0.0035 (10)	0.0030 (10)
N21B	0.0484 (15)	0.0331 (12)	0.0204 (10)	0.0101 (11)	0.0095 (10)	0.0066 (9)
N3B	0.0387 (13)	0.0273 (11)	0.0222 (11)	0.0068 (10)	0.0058 (9)	0.0042 (8)
C4B	0.0449 (17)	0.0369 (15)	0.0198 (13)	0.0038 (13)	0.0062 (11)	0.0065 (11)
O41B	0.0925 (19)	0.0416 (12)	0.0206 (10)	0.0231 (12)	0.0176 (10)	0.0065 (8)
C5B	0.0528 (19)	0.0310 (15)	0.0268 (13)	0.0058 (13)	0.0065 (12)	0.0090 (11)
C6B	0.0350 (15)	0.0295 (14)	0.0276 (13)	0.0007 (11)	0.0067 (11)	0.0053 (10)
C61B	0.058 (2)	0.0327 (15)	0.0355 (15)	0.0113 (14)	0.0110 (13)	0.0074 (12)
C1X	0.056 (2)	0.062 (2)	0.063 (2)	0.0006 (19)	−0.0014 (18)	0.0104 (18)
O2X	0.0551 (14)	0.0523 (13)	0.0358 (11)	0.0085 (11)	0.0142 (10)	−0.0087 (9)
C3X	0.0425 (18)	0.0505 (19)	0.058 (2)	−0.0014 (15)	0.0118 (15)	−0.0015 (15)
C5X	0.0462 (19)	0.068 (2)	0.0384 (17)	−0.0008 (17)	0.0120 (14)	−0.0209 (16)
N1X	0.042 (2)	0.051 (2)	0.0306 (18)	0.0049 (16)	0.0066 (14)	−0.0043 (15)
C2X	0.028 (2)	0.040 (2)	0.0277 (18)	−0.0011 (17)	0.0076 (14)	−0.0094 (17)
C4X	0.036 (2)	0.040 (2)	0.066 (3)	−0.0021 (18)	0.016 (2)	−0.018 (2)

Geometric parameters (Å, º) top

N1A—C2A	1.355 (4)	C1X—N1X	1.381 (5)
N1A—C6A	1.381 (4)	C1X—C4X'	1.476 (13)
N1A—H1A	0.8800	C1X—C2X'	1.664 (13)
C2A—N3A	1.327 (3)	C1X—H1XA	0.9800
C2A—N21A	1.337 (4)	C1X—H1XB	0.9800
N21A—H21A	0.8800	C1X—H1XC	0.9800
N21A—H21B	0.8800	C1X—H3XC	0.9900
N3A—C4A	1.386 (4)	C1X—H3XD	0.9900
C4A—O41A	1.247 (3)	O2X—C2X	1.227 (4)
C4A—C5A	1.448 (4)	O2X—C2X'	1.316 (12)
C5A—C6A	1.347 (4)	C3X—N1X'	1.310 (10)
C5A—H5A	0.9500	C3X—C4X	1.519 (5)
C6A—C61A	1.489 (4)	C3X—C2X	1.584 (5)
C61A—H61A	0.9800	C3X—H3XA	0.9900
C61A—H61B	0.9800	C3X—H3XB	0.9900
C61A—H61C	0.9800	C3X—H1XD	0.9800
N1B—C2B	1.321 (3)	C3X—H1XE	0.9800
N1B—C6B	1.371 (3)	C3X—H1XF	0.9800
C2B—N21B	1.339 (3)	C5X—N1X'	1.421 (10)
C2B—N3B	1.362 (3)	C5X—N1X	1.459 (4)
N21B—H21C	0.8800	C5X—C4X	1.526 (6)
N21B—H21D	0.8800	C5X—C4X'	1.527 (13)
N3B—C4B	1.388 (3)	C5X—H5XA	0.9900
N3B—H3B	0.8800	C5X—H5XB	0.9900
C4B—O41B	1.244 (3)	C5X—H5XC	0.9900
C4B—C5B	1.419 (4)	C5X—H5XD	0.9900
C5B—C6B	1.362 (4)	N1X—C2X	1.320 (5)
C5B—H5B	0.9500	C4X—H4XA	0.9900
C6B—C61B	1.498 (4)	C4X—H4XB	0.9900
C61B—H61D	0.9800	N1X'—C2X'	1.353 (15)
C61B—H61E	0.9800	C4X'—H4XC	0.9900
C61B—H61F	0.9800	C4X'—H4XD	0.9900

C2A—N1A—C6A	121.2 (2)	N1X'—C3X—C4X	63.2 (5)
C2A—N1A—H1A	119.4	C4X—C3X—C2X	102.7 (3)
C6A—N1A—H1A	119.4	N1X'—C3X—H3XA	120.5
N3A—C2A—N21A	120.0 (2)	C4X—C3X—H3XA	111.2
N3A—C2A—N1A	122.8 (3)	C2X—C3X—H3XA	111.2
N21A—C2A—N1A	117.2 (2)	N1X'—C3X—H3XB	128.6
C2A—N21A—H21A	120.0	C4X—C3X—H3XB	111.2
C2A—N21A—H21B	120.0	C2X—C3X—H3XB	111.2
H21A—N21A—H21B	120.0	H3XA—C3X—H3XB	109.1
C2A—N3A—C4A	118.9 (2)	N1X'—C3X—H1XD	109.5
O41A—C4A—N3A	119.3 (2)	C4X—C3X—H1XD	46.3
O41A—C4A—C5A	122.2 (3)	C2X—C3X—H1XD	149.1
N3A—C4A—C5A	118.4 (2)	H3XA—C3X—H1XD	85.8
C6A—C5A—C4A	120.5 (3)	H3XB—C3X—H1XD	85.2
C6A—C5A—H5A	119.8	N1X'—C3X—H1XE	109.5
C4A—C5A—H5A	119.8	C4X—C3X—H1XE	122.1
C5A—C6A—N1A	118.1 (2)	C2X—C3X—H1XE	85.4
C5A—C6A—C61A	125.5 (3)	H3XA—C3X—H1XE	118.7
N1A—C6A—C61A	116.4 (2)	H1XD—C3X—H1XE	109.5
C6A—C61A—H61A	109.5	N1X'—C3X—H1XF	109.5
C6A—C61A—H61B	109.5	C4X—C3X—H1XF	127.6
H61A—C61A—H61B	109.5	C2X—C3X—H1XF	89.5
C6A—C61A—H61C	109.5	H3XB—C3X—H1XF	111.0
H61A—C61A—H61C	109.5	H1XD—C3X—H1XF	109.5
H61B—C61A—H61C	109.5	H1XE—C3X—H1XF	109.5
C2B—N1B—C6B	116.7 (2)	N1X'—C5X—C4X	60.8 (5)
N1B—C2B—N21B	120.3 (2)	N1X—C5X—C4X	105.1 (3)
N1B—C2B—N3B	122.8 (2)	N1X'—C5X—C4X'	104.0 (7)
N21B—C2B—N3B	116.9 (2)	N1X—C5X—C4X'	59.8 (6)
C2B—N21B—H21C	120.0	C4X—C5X—C4X'	164.7 (6)
C2B—N21B—H21D	120.0	N1X'—C5X—H5XA	120.9
H21C—N21B—H21D	120.0	N1X—C5X—H5XA	110.7
C2B—N3B—C4B	122.5 (2)	C4X—C5X—H5XA	110.7
C2B—N3B—H3B	118.8	C4X'—C5X—H5XA	75.2
C4B—N3B—H3B	118.8	N1X'—C5X—H5XB	129.4
O41B—C4B—N3B	118.9 (2)	N1X—C5X—H5XB	110.7
O41B—C4B—C5B	126.2 (2)	C4X—C5X—H5XB	110.7
N3B—C4B—C5B	114.9 (2)	C4X'—C5X—H5XB	79.3
C6B—C5B—C4B	119.5 (2)	H5XA—C5X—H5XB	108.8
C6B—C5B—H5B	120.3	N1X'—C5X—H5XC	111.1
C4B—C5B—H5B	120.3	N1X—C5X—H5XC	119.5
C5B—C6B—N1B	123.7 (2)	C4X—C5X—H5XC	78.1
C5B—C6B—C61B	121.2 (2)	C4X'—C5X—H5XC	110.8
N1B—C6B—C61B	115.1 (2)	H5XA—C5X—H5XC	124.5
C6B—C61B—H61D	109.5	N1X'—C5X—H5XD	110.6
C6B—C61B—H61E	109.5	N1X—C5X—H5XD	130.6
H61D—C61B—H61E	109.5	C4X—C5X—H5XD	75.8
C6B—C61B—H61F	109.5	C4X'—C5X—H5XD	111.3
H61D—C61B—H61F	109.5	H5XB—C5X—H5XD	114.8
H61E—C61B—H61F	109.5	H5XC—C5X—H5XD	109.0
N1X—C1X—C4X'	62.8 (6)	C2X—N1X—C1X	121.6 (3)
C4X'—C1X—C2X'	97.8 (8)	C2X—N1X—C5X	114.5 (3)
N1X—C1X—H1XA	109.5	C1X—N1X—C5X	123.8 (3)
C4X'—C1X—H1XA	47.3	O2X—C2X—N1X	125.9 (4)
C2X'—C1X—H1XA	144.9	O2X—C2X—C3X	124.8 (4)
N1X—C1X—H1XB	109.5	N1X—C2X—C3X	109.3 (3)
C4X'—C1X—H1XB	118.0	C5X—C4X—C3X	107.6 (3)
C2X'—C1X—H1XB	89.1	C5X—C4X—H4XA	110.2
H1XA—C1X—H1XB	109.5	C3X—C4X—H4XA	110.2
N1X—C1X—H1XC	109.5	C5X—C4X—H4XB	110.2
C4X'—C1X—H1XC	131.8	C3X—C4X—H4XB	110.2
C2X'—C1X—H1XC	90.7	H4XA—C4X—H4XB	108.5
H1XA—C1X—H1XC	109.5	C2X'—N1X'—C3X	117.2 (9)
H1XB—C1X—H1XC	109.5	C2X'—N1X'—C5X	114.5 (9)
N1X—C1X—H3XC	119.1	C3X—N1X'—C5X	128.2 (8)
C4X'—C1X—H3XC	112.2	O2X—C2X'—N1X'	114.4 (11)
C2X'—C1X—H3XC	112.2	O2X—C2X'—C1X	136.3 (10)
H1XA—C1X—H3XC	83.7	N1X'—C2X'—C1X	109.2 (9)
H1XB—C1X—H3XC	121.6	C1X—C4X'—C5X	113.1 (9)
N1X—C1X—H3XD	128.8	C1X—C4X'—H4XC	109.0
C4X'—C1X—H3XD	112.2	C5X—C4X'—H4XC	109.0
C2X'—C1X—H3XD	112.2	C1X—C4X'—H4XD	109.0
H1XA—C1X—H3XD	89.2	C5X—C4X'—H4XD	109.0
H1XC—C1X—H3XD	107.9	H4XC—C4X'—H4XD	107.8
H3XC—C1X—H3XD	109.8

C6A—N1A—C2A—N3A	0.9 (4)	C5X—N1X—C2X—O2X	179.6 (3)
C6A—N1A—C2A—N21A	−179.8 (3)	C1X—N1X—C2X—C3X	−178.6 (3)
N21A—C2A—N3A—C4A	−179.3 (3)	C5X—N1X—C2X—C3X	0.2 (4)
N1A—C2A—N3A—C4A	−0.1 (4)	N1X'—C3X—C2X—O2X	−178.2 (9)
C2A—N3A—C4A—O41A	179.3 (3)	C4X—C3X—C2X—O2X	175.4 (3)
C2A—N3A—C4A—C5A	−0.1 (4)	N1X'—C3X—C2X—N1X	1.2 (8)
O41A—C4A—C5A—C6A	−179.9 (3)	C4X—C3X—C2X—N1X	−5.2 (4)
N3A—C4A—C5A—C6A	−0.6 (4)	N1X'—C5X—C4X—C3X	−3.1 (6)
C4A—C5A—C6A—N1A	1.3 (5)	N1X—C5X—C4X—C3X	−8.0 (4)
C4A—C5A—C6A—C61A	−179.4 (3)	C4X'—C5X—C4X—C3X	1 (3)
C2A—N1A—C6A—C5A	−1.5 (4)	N1X'—C3X—C4X—C5X	3.3 (6)
C2A—N1A—C6A—C61A	179.1 (3)	C2X—C3X—C4X—C5X	7.9 (4)
C6B—N1B—C2B—N21B	−179.9 (3)	C4X—C3X—N1X'—C2X'	174.6 (15)
C6B—N1B—C2B—N3B	0.5 (4)	C2X—C3X—N1X'—C2X'	1.5 (11)
N1B—C2B—N3B—C4B	1.7 (4)	C4X—C3X—N1X'—C5X	−4.3 (8)
N21B—C2B—N3B—C4B	−177.9 (3)	C2X—C3X—N1X'—C5X	−177.3 (16)
C2B—N3B—C4B—O41B	178.2 (3)	N1X—C5X—N1X'—C2X'	−1.3 (10)
C2B—N3B—C4B—C5B	−2.9 (4)	C4X—C5X—N1X'—C2X'	−174.5 (14)
O41B—C4B—C5B—C6B	−179.2 (3)	C4X'—C5X—N1X'—C2X'	6.7 (16)
N3B—C4B—C5B—C6B	2.0 (4)	N1X—C5X—N1X'—C3X	177.6 (15)
C4B—C5B—C6B—N1B	0.0 (5)	C4X—C5X—N1X'—C3X	4.4 (8)
C4B—C5B—C6B—C61B	−179.9 (3)	C4X'—C5X—N1X'—C3X	−174.4 (12)
C2B—N1B—C6B—C5B	−1.4 (4)	C2X—O2X—C2X'—N1X'	−1.2 (6)
C2B—N1B—C6B—C61B	178.6 (3)	C2X—O2X—C2X'—C1X	175 (3)
C4X'—C1X—N1X—C2X	172.1 (10)	C3X—N1X'—C2X'—O2X	−1 (2)
C2X'—C1X—N1X—C2X	1.6 (13)	C5X—N1X'—C2X'—O2X	177.6 (11)
C4X'—C1X—N1X—C5X	−6.6 (10)	C3X—N1X'—C2X'—C1X	−178.9 (9)
C2X'—C1X—N1X—C5X	−177.1 (13)	C5X—N1X'—C2X'—C1X	0.1 (17)
N1X'—C5X—N1X—C2X	−1.2 (7)	N1X—C1X—C2X'—O2X	−175 (3)
C4X—C5X—N1X—C2X	4.9 (4)	C4X'—C1X—C2X'—O2X	176 (2)
C4X'—C5X—N1X—C2X	−172.2 (10)	N1X—C1X—C2X'—N1X'	1.5 (6)
N1X'—C5X—N1X—C1X	177.5 (8)	C4X'—C1X—C2X'—N1X'	−7.0 (16)
C4X—C5X—N1X—C1X	−176.3 (4)	N1X—C1X—C4X'—C5X	5.7 (9)
C4X'—C5X—N1X—C1X	6.5 (10)	C2X'—C1X—C4X'—C5X	11.2 (15)
C2X'—O2X—C2X—N1X	−2.7 (16)	N1X'—C5X—C4X'—C1X	−12.0 (16)
C2X'—O2X—C2X—C3X	176.7 (19)	N1X—C5X—C4X'—C1X	−5.5 (8)
C1X—N1X—C2X—O2X	0.8 (6)	C4X—C5X—C4X'—C1X	−16 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O2X	0.88	2.00	2.800 (3)	151
N21A—H21A···O41B	0.88	1.92	2.794 (3)	173
N21A—H21B···O2X	0.88	2.09	2.869 (3)	146
N3B—H3B···N3A	0.88	1.97	2.838 (3)	171
N21B—H21D···O41A	0.88	2.01	2.888 (3)	179
N21B—H21C···N1Bⁱ	0.88	2.09	2.962 (3)	172

Symmetry code: (i) −x+1, −y+2, −z+2.

Experimental details

	(I)	(Ia)	(Ib)	(Ic)
Crystal data
Chemical formula	C₄H₆N₄O	C₄H₆N₄O·4/3C₃H₇NO·1/3H₂O	C₄H₆N₄O·C₄H₉NO	C₄H₆N₄O·3/2C₅H₉NO
M_r	126.13	229.59	213.25	274.83
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁	Monoclinic, Cc	Triclinic, P1
Temperature (K)	173	173	173	173
a, b, c (Å)	7.7150 (9), 9.7229 (7), 7.4514 (8)	7.4417 (6), 25.3217 (18), 9.8578 (7)	19.1494 (13), 7.8704 (4), 14.9104 (11)	8.4550 (9), 10.0803 (9), 17.0735 (15)
α, β, γ (°)	90, 114.453 (8), 90	90, 108.476 (6), 90	90, 104.868 (6), 90	75.558 (7), 78.222 (8), 81.363 (8)
V (Å³)	508.81 (9)	1761.8 (2)	2172.0 (2)	1371.9 (2)
Z	4	6	8	4
Radiation type	Mo Kα	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.13	0.10	0.10	0.10
Crystal size (mm)	0.45 × 0.35 × 0.30	0.50 × 0.30 × 0.20	0.50 × 0.35 × 0.30	0.25 × 0.20 × 0.20

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer	Stoe IPDS II two-circle diffractometer	Stoe IPDS II two-circle diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	–	–	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7117, 953, 737	28505, 3380, 2636	12494, 2054, 1922	18821, 5116, 2940
R_int	0.128	0.170	0.096	0.091
(sin θ/λ)_max (Å⁻¹)	0.608	0.610	0.609	0.609

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.092, 0.97	0.040, 0.085, 0.91	0.047, 0.126, 1.04	0.056, 0.127, 0.91
No. of reflections	953	3380	2054	5116
No. of parameters	103	459	277	355
No. of restraints	0	4	22	0
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement	H atoms treated by a mixture of independent and constrained refinement	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.29	0.19, −0.19	0.47, −0.31	0.48, −0.29

	(IIa)	(IIb)
Crystal data
Chemical formula	C₅H₇N₃O·C₅H₇N₃O·C₄H₉NO	C₅H₇N₃O·C₅H₇N₃O·C₅H9NO
M_r	337.39	349.40
Crystal system, space group	Triclinic, P1	Triclinic, P1
Temperature (K)	173	173
a, b, c (Å)	7.8763 (13), 9.6078 (17), 12.3115 (19)	7.3321 (7), 9.8805 (9), 12.5860 (12)
α, β, γ (°)	108.780 (13), 95.194 (13), 99.959 (13)	102.835 (7), 98.830 (8), 91.555 (8)
V (Å³)	858.0 (2)	876.70 (14)
Z	2	2
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.10	0.10
Crystal size (mm)	0.40 × 0.25 × 0.10	0.45 × 0.35 × 0.25

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	–	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7199, 3208, 1427	13229, 3267, 1883
R_int	0.131	0.149
(sin θ/λ)_max (Å⁻¹)	0.609	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.204, 0.82	0.068, 0.176, 0.82
No. of reflections	3208	3267
No. of parameters	223	242
No. of restraints	0	16
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.47	0.34, −0.35

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Version 2.2; Macrae et al., 2008) and XP (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) for (I) top

D—H···A	D—H	H···A	D···A	D—H···A
N21—H21A···O41ⁱ	0.90 (2)	1.98 (2)	2.8678 (17)	165.9 (19)
N21—H21B···N61ⁱⁱ	0.89 (2)	2.34 (2)	3.1304 (19)	147.9 (18)
N3—H3···N1ⁱⁱ	0.92 (2)	2.15 (2)	3.0370 (17)	163.2 (17)
N61—H61B···N1ⁱⁱⁱ	0.89 (2)	2.34 (2)	3.2131 (18)	166.8 (16)
N61—H61A···O41^iv	0.89 (2)	2.05 (2)	2.9296 (18)	172.5 (17)

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

Hydrogen-bond geometry (Å, º) for (Ia) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N1Bⁱ	0.88	2.11	2.985 (4)	170
N21A—H21B···O1Xⁱ	0.88	2.12	2.820 (4)	136
N3A—H3A···O41B	0.88	1.86	2.734 (3)	175
N61A—H61B···O1W	0.88	2.05	2.872 (4)	155
N21B—H21C···N1Aⁱⁱ	0.88	2.05	2.931 (4)	175
N21B—H21D···O1V	0.88	2.07	2.920 (4)	161
N3B—H3B···O41A	0.88	1.95	2.812 (3)	167
N61B—H61C···O1X	0.88	2.16	3.028 (4)	168
N61B—H61D···O41C	0.88	2.02	2.886 (4)	169
N21C—H21E···O41Aⁱⁱⁱ	0.88	2.11	2.945 (4)	158
N21C—H21F···O1Z	0.88	2.10	2.874 (4)	146
N3C—H3C···O1V^iv	0.88	2.03	2.890 (3)	166
N61C—H61E···O41C^v	0.88	1.97	2.744 (3)	147
N61C—H61F···O1Y	0.88	2.07	2.949 (4)	173
O1V—H1V···N1C^vi	0.844 (10)	2.060 (17)	2.856 (3)	157 (3)
O1V—H2V···O41A	0.844 (10)	1.957 (18)	2.751 (3)	156 (4)

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

Hydrogen-bond geometry (Å, º) for (Ib) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N1B	0.88	2.07	2.946 (4)	171
N21A—H21B···O2X	0.88	2.46	3.176 (4)	139
N3A—H3A···O41Bⁱ	0.88	1.89	2.765 (3)	174
N61A—H61A···O2Xⁱⁱ	0.88	2.15	2.939 (4)	150
N61A—H61B···O41Bⁱⁱⁱ	0.88	2.22	2.975 (4)	144
N21B—H21C···N1A	0.88	2.16	3.029 (4)	172
N3B—H3B···O41A^iv	0.88	1.84	2.700 (4)	166
N61B—H61C···O2X	0.88	2.17	2.960 (4)	149
N61B—H61D···O41A^v	0.88	1.95	2.813 (4)	165

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

Hydrogen-bond geometry (Å, º) for (Ic) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···O2Xⁱ	0.88	2.22	3.092 (3)	169
N21A—H21B···O41B	0.88	2.00	2.756 (3)	143
N3A—H3A···O41Aⁱⁱ	0.88	1.87	2.750 (3)	177
N61A—H61A···N1Aⁱ	0.88	2.15	3.023 (3)	169
N61A—H61B···O2X	0.88	2.14	2.891 (3)	142
N21B—H21C···O2Zⁱⁱⁱ	0.88	2.12	2.989 (3)	170
N21B—H21D···O2Y	0.88	2.06	2.832 (3)	146
N3B—H3B···O2Y	0.88	2.15	2.904 (3)	143
N61B—H61C···N1Bⁱⁱⁱ	0.88	2.13	3.001 (3)	170
N61B—H61D···O2Z	0.88	2.11	2.840 (3)	139

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

Hydrogen-bond geometry (Å, º) for (IIa) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···O41B	0.88	1.92	2.803 (4)	178
N21A—H21B···O2X	0.88	2.06	2.843 (4)	147
N1A—H1A···O2X	0.88	2.02	2.807 (4)	149
N3B—H3B···N3A	0.88	1.97	2.844 (4)	177
N21B—H21C···N1Bⁱ	0.88	2.10	2.969 (4)	172
N21B—H21D···O41A	0.88	2.00	2.877 (4)	173

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º) for (IIb) top

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O2X	0.88	2.00	2.800 (3)	151
N21A—H21A···O41B	0.88	1.92	2.794 (3)	173
N21A—H21B···O2X	0.88	2.09	2.869 (3)	146
N3B—H3B···N3A	0.88	1.97	2.838 (3)	171
N21B—H21D···O41A	0.88	2.01	2.888 (3)	179
N21B—H21C···N1Bⁱ	0.88	2.09	2.962 (3)	172

Symmetry code: (i) −x+1, −y+2, −z+2.

Crystallization of 2,6-diaminopyrimidin-4-one top

Crystal	2,6-Diaminopyrimidin-4-one (mg; mmol)	Solvent	Temperature
(I)	4.2; 0.033	Methanol (500 µl)	323 K
(Ia)	1.9; 0.015	DMF (100 µl)	Room temperature
(Ib)	2.1; 0.017	DMAC (200 µl)	323 K
(Ic)	3.0; 0.024	NMP (50 µl)	Room temperature

Crystallization of 2-amino-6-methylpyrimidin-4-one top

Crystal	2-Amino-6-methylpyrimidin-4-one (mg; mmol)	Solvent	Temperature
(IIa)	2.3; 0.018	DMAC (150 µl)	277 K
(IIb)	1.9; 0.015	NMP (50 µl)	323 K

Acknowledgements

The authors thank Professor Dr Ernst Egert for helpful discussions.

References

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STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 67| Part 5| May 2011| Pages o179-o187

doi:10.1107/S0108270111013072

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Pseudopolymorphs of 2,6-di­amino­pyrimidin-4-one and 2-amino-6-methyl­pyrimidin-4-one: one or two tautomers present in the same crystal

Comment

Experimental

Compound (I)

Crystal data

Data collection

Refinement

Compound (Ia)

Crystal data

Data collection

Refinement

Compound (Ib)

Crystal data

Data collection

Refinement

Compound (Ic)

Crystal data

Data collection

Refinement

Compound (IIa)

Crystal data

Data collection

Refinement

Compound (IIb)

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Pseudopolymorphs of 2,6-diaminopyrimidin-4-one and 2-amino-6-methylpyrimidin-4-one: one or two tautomers present in the same crystal