One barbiturate and two solvated thio­barbiturates containing the triply hydrogen-bonded ADA/DAD synthon, plus one ansolvate and three solvates of their coformer 2,4-di­amino­pyrimidine

A path to new synthons for application in crystal engineering is the replacement of a strong hydrogen-bond acceptor, like a C=O group, with a weaker acceptor, like a C=S group, in doubly or triply hydrogen-bonded synthons. For instance, if the C=O group at the 2-position of barbituric acid is changed into a C=S group, 2-thio­barbituric acid is obtained. Each of the compounds comprises two ADA hydrogen-bonding sites (D = donor and A = acceptor). We report the results of cocrystallization experiments of barbituric acid and 2-thio­barbituric acid, respectively, with 2,4-di­amino­pyrimidine, which contains a complementary DAD hydrogen-bonding site and is therefore capable of forming an ADA/DAD synthon with barbituric acid and 2-thio­barbituric acid. In addition, pure 2,4-di­amino­pyrimidine was crystallized in order to study its preferred hydrogen-bonding motifs. The experiments yielded one ansolvate of 2,4-di­amino­pyrimidine (pyrimidine-2,4-di­amine, DAPY), C₄H₆N₄, (I), three solvates of DAPY, namely 2,4-di­amino­pyrimidine-1,4-dioxane (2/1), 2C₄H₆N₄·C₄H₈O₂, (II), 2,4-di­amino­pyrimidine-N,N-di­methyl­acetamide (1/1), C₄H₆N₄·C₄H₉NO, (III), and 2,4-di­amino­pyrimidine-1-methyl­pyrrolidin-2-one (1/1), C₄H₆N₄·C₅H₉NO, (IV), one salt of barbituric acid, viz. 2,4-di­amino­pyrimidinium barbiturate (barbiturate is 2,4,6-trioxopyrimidin-5-ide), C₄H₇N₄⁺·C₄H₃N₂O₃^-, (V), and two solvated salts of 2-thio­barbituric acid, viz. 2,4-di­amino­pyrimi­dinium 2-thio­barbiturate-N,N-di­methyl­formamide (1/2) (2-thio­barbiturate is 4,6-dioxo-2-sulfanylidenepy­rimidin-5-ide), C₄H₇N₄⁺·C₄H₃N₂O₂S^-·2C₃H₇NO, (VI), and 2,4-di­amino­pyrimidinium 2-thio­barbiturate-N,N-di­methyl­acetamide (1/2), C₄H₇N₄⁺·C₄H₃N₂O₂S^-·2C₄H₉NO, (VII). The ADA/DAD synthon was succesfully formed in the salt of barbituric acid, i.e. (V), as well as in the salts of 2-thio­barbituric acid, i.e. (VI) and (VII). In the crystal structures of 2,4-di­amino­pyrimidine, i.e. (I)-(IV), R₂²(8) N-H...N hydrogen-bond motifs are preferred and, in two structures, additional R₃²(8) patterns were observed.

Computing details

Data collection: X-AREA (Stoe & Cie, 2001) for (I), (II), (IV), (V), (VI), (VII); SMART (Siemens, 1995) for (III). Cell refinement: X-AREA (Stoe & Cie, 2001) for (I), (II), (IV), (V), (VI), (VII); SMART (Siemens, 1995) for (III). Data reduction: X-AREA (Stoe & Cie, 2001) for (I), (II), (IV), (V), (VI), (VII); SAINT (Siemens, 1995) for (III). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL (Sheldrick, 2015) for (I), (II), (III), (IV), (V), (VI); SHELXL2014 (Sheldrick, 2015) for (VII). For all compounds, molecular graphics: Mercury (Version 3.8, Macrae et al., 2008) and XP in SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

(I) Pyrimidine-2,4-diamine

Crystal data

C4H6N4	F(000) = 232
Mr = 110.13	Dx = 1.479 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.0330 (17) Å	Cell parameters from 4847 reflections
b = 4.0256 (3) Å	θ = 3.5–26.2°
c = 11.5992 (15) Å	µ = 0.10 mm^−1
β = 118.346 (10)°	T = 173 K
V = 494.50 (11) Å^3	Block, colourless
Z = 4	0.12 × 0.10 × 0.07 mm

Data collection

Stoe IPDS II two-circle diffractometer	859 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.067
ω scans	θmax = 25.8°, θmin = 3.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −14→14
Tmin = 0.599, Tmax = 1.000	k = −4→4
3858 measured reflections	l = −14→14
942 independent reflections

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.110	w = 1/[σ^2(Fo^2) + (0.0555P)^2 + 0.1736P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
942 reflections	Δρmax = 0.18 e Å^−3
85 parameters	Δρmin = −0.18 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
N1A	0.10545 (11)	0.5124 (3)	0.40709 (11)	0.0234 (3)
C2A	0.19733 (13)	0.4072 (4)	0.38121 (13)	0.0210 (4)
N21A	0.16100 (12)	0.2171 (4)	0.27343 (12)	0.0263 (3)
H21A	0.0819 (15)	0.154 (5)	0.2297 (17)	0.032*
H22A	0.2212 (16)	0.121 (5)	0.2652 (18)	0.032*
N3A	0.32171 (11)	0.4780 (3)	0.45018 (11)	0.0213 (3)
C4A	0.35685 (13)	0.6656 (4)	0.55740 (13)	0.0211 (4)
N41A	0.48219 (12)	0.7340 (4)	0.63038 (12)	0.0269 (4)
H41A	0.5314 (17)	0.686 (5)	0.5972 (18)	0.032*
H42A	0.4998 (17)	0.895 (4)	0.6869 (16)	0.032*
C5A	0.26958 (14)	0.7780 (4)	0.59615 (14)	0.0245 (4)
H5A	0.2949	0.9036	0.6740	0.029*
C6A	0.14574 (14)	0.6977 (4)	0.51600 (14)	0.0244 (4)
H6A	0.0845	0.7780	0.5388	0.029*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0180 (6)	0.0285 (7)	0.0227 (6)	0.0023 (5)	0.0089 (5)	0.0040 (5)
C2A	0.0185 (7)	0.0240 (8)	0.0182 (6)	0.0005 (5)	0.0070 (5)	0.0050 (5)
N21A	0.0174 (6)	0.0372 (8)	0.0227 (6)	−0.0049 (5)	0.0081 (5)	−0.0063 (5)
N3A	0.0189 (6)	0.0244 (7)	0.0196 (6)	0.0004 (5)	0.0084 (5)	0.0011 (5)
C4A	0.0201 (7)	0.0213 (7)	0.0186 (6)	0.0017 (5)	0.0066 (5)	0.0039 (5)
N41A	0.0188 (7)	0.0346 (8)	0.0242 (6)	−0.0009 (5)	0.0078 (5)	−0.0071 (5)
C5A	0.0244 (8)	0.0279 (8)	0.0216 (7)	0.0018 (6)	0.0112 (6)	−0.0006 (6)
C6A	0.0233 (8)	0.0269 (8)	0.0253 (7)	0.0053 (6)	0.0133 (6)	0.0043 (6)

Geometric parameters (Å, º)

N1A—C6A	1.3439 (19)	C4A—N41A	1.3619 (19)
N1A—C2A	1.3443 (19)	C4A—C5A	1.399 (2)
C2A—N21A	1.3493 (19)	N41A—H41A	0.867 (15)
C2A—N3A	1.3506 (18)	N41A—H42A	0.874 (15)
N21A—H21A	0.876 (15)	C5A—C6A	1.369 (2)
N21A—H22A	0.865 (15)	C5A—H5A	0.9500
N3A—C4A	1.3403 (19)	C6A—H6A	0.9500
C6A—N1A—C2A	114.64 (12)	N41A—C4A—C5A	120.89 (14)
N1A—C2A—N21A	116.53 (13)	C4A—N41A—H41A	117.9 (13)
N1A—C2A—N3A	126.78 (13)	C4A—N41A—H42A	114.8 (12)
N21A—C2A—N3A	116.67 (13)	H41A—N41A—H42A	121.6 (18)
C2A—N21A—H21A	119.0 (12)	C6A—C5A—C4A	116.51 (14)
C2A—N21A—H22A	115.8 (12)	C6A—C5A—H5A	121.7
H21A—N21A—H22A	122.9 (18)	C4A—C5A—H5A	121.7
C4A—N3A—C2A	116.18 (12)	N1A—C6A—C5A	124.06 (14)
N3A—C4A—N41A	117.33 (13)	N1A—C6A—H6A	118.0
N3A—C4A—C5A	121.74 (13)	C5A—C6A—H6A	118.0
C6A—N1A—C2A—N21A	179.29 (13)	C2A—N3A—C4A—C5A	0.7 (2)
C6A—N1A—C2A—N3A	−2.3 (2)	N3A—C4A—C5A—C6A	−2.5 (2)
N1A—C2A—N3A—C4A	1.9 (2)	N41A—C4A—C5A—C6A	179.72 (13)
N21A—C2A—N3A—C4A	−179.69 (12)	C2A—N1A—C6A—C5A	0.1 (2)
C2A—N3A—C4A—N41A	178.51 (12)	C4A—C5A—C6A—N1A	2.1 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N1A^i	0.88 (2)	2.13 (2)	2.9947 (18)	170 (2)
N41A—H41A···N3A^ii	0.87 (2)	2.19 (2)	3.0436 (19)	169 (2)
N41A—H42A···N41A^iii	0.87 (2)	2.44 (2)	3.287 (2)	163 (2)

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

(II) Pyrimidine-2,4-diamine–1,4-dioxane (2/1)

Crystal data

C4H6N4·0.5C4H8O2	F(000) = 328
Mr = 154.18	Dx = 1.372 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 7.6282 (14) Å	Cell parameters from 5777 reflections
b = 7.2157 (9) Å	θ = 3.6–26.0°
c = 13.879 (2) Å	µ = 0.10 mm^−1
β = 102.243 (15)°	T = 173 K
V = 746.6 (2) Å^3	Block, colourless
Z = 4	0.40 × 0.30 × 0.27 mm

Data collection

Stoe IPDS II two-circle diffractometer	1261 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.031
ω scans	θmax = 25.6°, θmin = 3.9°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→8
Tmin = 0.659, Tmax = 1.000	k = −8→8
4207 measured reflections	l = −16→16
1388 independent reflections

Refinement

Refinement on F^2	4 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.0412P)^2 + 0.3097P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max < 0.001
1388 reflections	Δρmax = 0.20 e Å^−3
112 parameters	Δρmin = −0.18 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
N1A	0.75873 (16)	0.66790 (15)	0.70609 (9)	0.0235 (3)
C2A	0.85588 (18)	0.51618 (17)	0.69617 (9)	0.0188 (3)
N21A	1.03684 (16)	0.52854 (16)	0.72415 (9)	0.0243 (3)
H21A	1.074 (2)	0.626 (2)	0.7623 (12)	0.029*
H22A	1.095 (2)	0.420 (2)	0.7363 (12)	0.029*
N3A	0.79084 (15)	0.35175 (15)	0.65921 (8)	0.0194 (3)
C4A	0.61275 (18)	0.33566 (18)	0.62983 (9)	0.0198 (3)
N41A	0.55124 (16)	0.16881 (17)	0.59471 (10)	0.0272 (3)
H42A	0.4348 (19)	0.149 (2)	0.5746 (13)	0.033*
H41A	0.631 (2)	0.087 (2)	0.5877 (13)	0.033*
C5A	0.49884 (19)	0.4861 (2)	0.63736 (10)	0.0248 (3)
H5A	0.3722	0.4767	0.6170	0.030*
C6A	0.58051 (19)	0.6459 (2)	0.67547 (11)	0.0254 (3)
H6A	0.5061	0.7493	0.6808	0.031*
O1X	0.81612 (13)	−0.03406 (14)	0.49648 (7)	0.0265 (3)
C1X	0.94006 (19)	−0.1825 (2)	0.49452 (11)	0.0260 (3)
H1X1	0.9411	−0.2145	0.4253	0.031*
H1X2	0.9011	−0.2934	0.5264	0.031*
C2X	0.87426 (19)	0.1282 (2)	0.45266 (11)	0.0269 (3)
H2X1	0.7902	0.2315	0.4558	0.032*
H2X2	0.8736	0.1036	0.3824	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0236 (6)	0.0170 (6)	0.0293 (6)	0.0019 (4)	0.0039 (5)	−0.0007 (5)
C2A	0.0217 (7)	0.0163 (6)	0.0182 (6)	−0.0006 (5)	0.0038 (5)	0.0023 (5)
N21A	0.0192 (6)	0.0157 (6)	0.0357 (7)	−0.0011 (5)	0.0010 (5)	−0.0029 (5)
N3A	0.0183 (6)	0.0168 (6)	0.0225 (6)	−0.0002 (4)	0.0029 (4)	−0.0010 (4)
C4A	0.0198 (7)	0.0207 (7)	0.0186 (6)	−0.0006 (5)	0.0033 (5)	0.0009 (5)
N41A	0.0167 (6)	0.0235 (6)	0.0399 (7)	−0.0020 (5)	0.0028 (5)	−0.0084 (5)
C5A	0.0176 (7)	0.0255 (7)	0.0301 (7)	0.0028 (5)	0.0027 (5)	−0.0010 (6)
C6A	0.0243 (7)	0.0220 (7)	0.0295 (7)	0.0068 (6)	0.0045 (6)	0.0003 (6)
O1X	0.0170 (5)	0.0286 (6)	0.0344 (6)	0.0007 (4)	0.0068 (4)	−0.0020 (4)
C1X	0.0240 (7)	0.0237 (7)	0.0312 (7)	0.0009 (6)	0.0080 (6)	−0.0020 (6)
C2X	0.0245 (7)	0.0282 (7)	0.0273 (7)	0.0056 (6)	0.0040 (6)	0.0023 (6)

Geometric parameters (Å, º)

N1A—C6A	1.3450 (19)	C5A—C6A	1.363 (2)
N1A—C2A	1.3452 (17)	C5A—H5A	0.9500
C2A—N3A	1.3450 (17)	C6A—H6A	0.9500
C2A—N21A	1.3553 (18)	O1X—C1X	1.4327 (17)
N21A—H21A	0.891 (14)	O1X—C2X	1.4324 (18)
N21A—H22A	0.895 (14)	C1X—C2X^i	1.502 (2)
N3A—C4A	1.3380 (17)	C1X—H1X1	0.9900
C4A—N41A	1.3454 (18)	C1X—H1X2	0.9900
C4A—C5A	1.4079 (19)	C2X—C1X^i	1.502 (2)
N41A—H42A	0.884 (14)	C2X—H2X1	0.9900
N41A—H41A	0.870 (14)	C2X—H2X2	0.9900
C6A—N1A—C2A	114.42 (11)	N1A—C6A—C5A	124.80 (12)
N1A—C2A—N3A	126.17 (12)	N1A—C6A—H6A	117.6
N1A—C2A—N21A	117.83 (12)	C5A—C6A—H6A	117.6
N3A—C2A—N21A	115.99 (11)	C1X—O1X—C2X	109.76 (10)
C2A—N21A—H21A	113.6 (11)	O1X—C1X—C2X^i	110.70 (12)
C2A—N21A—H22A	115.3 (11)	O1X—C1X—H1X1	109.5
H21A—N21A—H22A	119.7 (15)	C2X^i—C1X—H1X1	109.5
C4A—N3A—C2A	117.47 (11)	O1X—C1X—H1X2	109.5
N3A—C4A—N41A	116.21 (12)	C2X^i—C1X—H1X2	109.5
N3A—C4A—C5A	120.88 (12)	H1X1—C1X—H1X2	108.1
N41A—C4A—C5A	122.91 (13)	O1X—C2X—C1X^i	110.53 (11)
C4A—N41A—H42A	120.6 (11)	O1X—C2X—H2X1	109.5
C4A—N41A—H41A	116.7 (12)	C1X^i—C2X—H2X1	109.5
H42A—N41A—H41A	122.5 (16)	O1X—C2X—H2X2	109.5
C6A—C5A—C4A	116.26 (13)	C1X^i—C2X—H2X2	109.5
C6A—C5A—H5A	121.9	H2X1—C2X—H2X2	108.1
C4A—C5A—H5A	121.9
C6A—N1A—C2A—N3A	0.3 (2)	N3A—C4A—C5A—C6A	0.2 (2)
C6A—N1A—C2A—N21A	179.06 (12)	N41A—C4A—C5A—C6A	179.24 (13)
N1A—C2A—N3A—C4A	−0.43 (19)	C2A—N1A—C6A—C5A	0.2 (2)
N21A—C2A—N3A—C4A	−179.24 (11)	C4A—C5A—C6A—N1A	−0.4 (2)
C2A—N3A—C4A—N41A	−178.93 (12)	C2X—O1X—C1X—C2X^i	57.71 (16)
C2A—N3A—C4A—C5A	0.17 (18)	C1X—O1X—C2X—C1X^i	−57.62 (16)

Symmetry code: (i) −x+2, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N3A^ii	0.89 (1)	2.10 (1)	2.9809 (16)	168 (2)
N21A—H22A···N1A^iii	0.90 (1)	2.20 (1)	3.0824 (17)	170 (2)
N41A—H42A···O1X^iv	0.88 (1)	2.13 (2)	2.9826 (17)	163 (2)
N41A—H41A···O1X	0.87 (1)	2.26 (2)	3.0418 (17)	150 (2)

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

(III) Pyrimidine-2,4-diamine–N,N-dimethylacetamide (1/1)

Crystal data

C4H6N4·C4H9NO	Z = 2
Mr = 197.25	F(000) = 212
Triclinic, P1	Dx = 1.263 Mg m^−3
a = 8.0055 (10) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.0256 (10) Å	Cell parameters from 2889 reflections
c = 9.3143 (11) Å	θ = 3–23°
α = 81.779 (2)°	µ = 0.09 mm^−1
β = 78.053 (2)°	T = 180 K
γ = 62.518 (2)°	Block, colourless
V = 518.63 (11) Å^3	0.50 × 0.40 × 0.40 mm

Data collection

Siemens CCD three-circle diffractometer	1346 reflections with I > 2σ(I)
ω scans	Rint = 0.111
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	θmax = 28.2°, θmin = 2.2°
Tmin = 0.648, Tmax = 1.000	h = −10→10
5287 measured reflections	k = −10→10
2204 independent reflections	l = −11→12

Refinement

Refinement on F^2	132 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.113	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.286	w = 1/[σ^2(Fo^2) + (0.1438P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.004
2204 reflections	Δρmax = 0.40 e Å^−3
161 parameters	Δρmin = −0.44 e Å^−3

Special details

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

Refinement. The used target distances were 1.52 (1) Å for d(C1X/Y,C2X/Y) and d(C31X/Y,C2X'/Y'), 1.25 (1) Å for d(C2X/Y,O21X/Y) and d(C2X'/Y',O21X/Y), 1.30 (1) Å for d(C2X/Y,N3X/Y) and d(C2X'/Y',N3X'/Y'), 1.47 (1) Å for d(N3X/Y,C31X/Y), d(N3X/Y,C32X/Y), d(N3X'/Y',C1X/Y) and d(N3X'/Y',C32X/Y), 2.42 (2) Å for d(O21X/Y,C1X/Y) and d(O21X/Y,C31X/Y), 2.23 (2) Å for d(O21X/Y,N3X/Y) and d(O21X/Y,N3X'/Y'), 2.41 (2) Å for d(C1X/Y,N3X/Y) and d(C31X/Y,N3X'/Y'), 2.41 (2) Å for d(C2X/Y,C31X/Y) and d(C2X'/Y',C1X/Y), 2.43 (2) Å for d(C2X/Y,C32X/Y) and d(C2X'/Y',C32X/Y), and 2.52 (2) Å for d(C31X/Y,C32X/Y) and d(C1X/Y,C32X/Y).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.4732 (4)	0.8072 (4)	0.1346 (3)	0.0350 (8)
C2A	0.3274 (4)	0.9497 (4)	0.2107 (4)	0.0278 (8)
N21A	0.2895 (4)	1.1261 (4)	0.1531 (4)	0.0393 (9)
H21A	0.191 (4)	1.214 (4)	0.209 (4)	0.047*
H22A	0.357 (5)	1.143 (5)	0.067 (3)	0.047*
N3A	0.2167 (4)	0.9340 (4)	0.3361 (3)	0.0292 (7)
C4A	0.2544 (5)	0.7604 (4)	0.3956 (3)	0.0272 (8)
N41A	0.1479 (4)	0.7454 (4)	0.5218 (3)	0.0370 (8)
H41A	0.047 (4)	0.838 (4)	0.566 (4)	0.044*
H42A	0.154 (5)	0.638 (4)	0.562 (4)	0.044*
C5A	0.4054 (5)	0.6019 (5)	0.3255 (4)	0.0350 (9)
H5A	0.4354	0.4774	0.3651	0.042*
C6A	0.5045 (5)	0.6371 (5)	0.1993 (4)	0.0369 (9)
H6A	0.6064	0.5313	0.1516	0.044*
C1X	−0.0800 (6)	0.3330 (6)	0.9231 (4)	0.0534 (11)
H1XA	0.0035	0.2812	0.9980	0.080*	0.808 (7)
H1XB	−0.1340	0.2478	0.9152	0.080*	0.808 (7)
H1XC	−0.1835	0.4563	0.9510	0.080*	0.808 (7)
H1XD	−0.1027	0.2494	1.0038	0.080*	0.192 (7)
H1XE	−0.0437	0.4176	0.9607	0.080*	0.192 (7)
H1XF	−0.1967	0.4073	0.8801	0.080*	0.192 (7)
O21X	0.0132 (4)	0.5078 (3)	0.7128 (3)	0.0445 (8)
C31X	0.2694 (5)	0.2146 (5)	0.5704 (4)	0.0456 (10)
H3XA	0.1908	0.3304	0.5174	0.068*	0.808 (7)
H3XB	0.3042	0.1061	0.5138	0.068*	0.808 (7)
H3XC	0.3855	0.2194	0.5836	0.068*	0.808 (7)
H3XD	0.3122	0.0799	0.5954	0.068*	0.192 (7)
H3XE	0.2178	0.2478	0.4781	0.068*	0.192 (7)
H3XF	0.3776	0.2440	0.5589	0.068*	0.192 (7)
C32X	0.2036 (7)	0.0120 (5)	0.7926 (6)	0.0637 (14)
H4XA	0.2050	0.0210	0.8961	0.096*	0.808 (7)
H4XB	0.3283	−0.0826	0.7486	0.096*	0.808 (7)
H4XC	0.1047	−0.0248	0.7856	0.096*	0.808 (7)
H4XD	0.1693	−0.0585	0.8786	0.096*	0.192 (7)
H4XE	0.1871	−0.0270	0.7036	0.096*	0.192 (7)
H4XF	0.3370	−0.0134	0.7856	0.096*	0.192 (7)
C2X	0.0343 (6)	0.3544 (6)	0.7763 (5)	0.0353 (12)	0.808 (7)
N3X	0.1626 (5)	0.1969 (5)	0.7131 (4)	0.0383 (12)	0.808 (7)
C2X'	0.1122 (19)	0.3290 (11)	0.6951 (13)	0.032 (4)	0.192 (7)
N3X'	0.0777 (16)	0.2178 (11)	0.8076 (12)	0.034 (4)	0.192 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0329 (16)	0.0252 (16)	0.0372 (17)	−0.0077 (13)	0.0045 (13)	−0.0061 (13)
C2A	0.0222 (17)	0.0211 (17)	0.036 (2)	−0.0053 (13)	−0.0044 (14)	−0.0047 (13)
N21A	0.0396 (19)	0.0199 (15)	0.0411 (19)	−0.0045 (13)	0.0084 (14)	−0.0028 (13)
N3A	0.0273 (15)	0.0220 (14)	0.0326 (16)	−0.0060 (12)	−0.0045 (12)	−0.0030 (11)
C4A	0.0289 (18)	0.0212 (17)	0.0308 (19)	−0.0093 (14)	−0.0074 (15)	−0.0030 (13)
N41A	0.0366 (17)	0.0179 (15)	0.0440 (19)	−0.0055 (13)	0.0045 (14)	−0.0036 (13)
C5A	0.0317 (19)	0.0180 (17)	0.046 (2)	−0.0043 (14)	−0.0016 (16)	−0.0035 (14)
C6A	0.035 (2)	0.0202 (18)	0.040 (2)	−0.0024 (15)	0.0031 (16)	−0.0073 (14)
C1X	0.052 (3)	0.059 (3)	0.046 (2)	−0.023 (2)	−0.0052 (19)	−0.001 (2)
O21X	0.0479 (16)	0.0211 (13)	0.0535 (17)	−0.0097 (11)	0.0000 (13)	−0.0011 (11)
C31X	0.036 (2)	0.037 (2)	0.058 (2)	−0.0086 (17)	−0.0013 (18)	−0.0209 (18)
C32X	0.070 (3)	0.0178 (19)	0.104 (4)	−0.0106 (19)	−0.043 (3)	0.004 (2)
C2X	0.036 (3)	0.030 (3)	0.040 (3)	−0.014 (2)	−0.011 (2)	0.003 (2)
N3X	0.032 (2)	0.025 (2)	0.053 (3)	−0.0074 (18)	−0.0078 (18)	−0.0065 (18)
C2X'	0.035 (9)	0.032 (6)	0.044 (9)	−0.030 (7)	0.001 (6)	−0.008 (6)
N3X'	0.030 (8)	0.024 (6)	0.048 (8)	−0.010 (6)	−0.016 (5)	0.008 (6)

Geometric parameters (Å, º)

N1A—C6A	1.342 (4)	C1X—H1XF	0.9800
N1A—C2A	1.353 (4)	O21X—C2X	1.240 (4)
C2A—N3A	1.341 (4)	O21X—C2X'	1.296 (8)
C2A—N21A	1.355 (4)	C31X—N3X	1.451 (5)
N21A—H21A	0.898 (19)	C31X—C2X'	1.552 (8)
N21A—H22A	0.901 (19)	C31X—H3XA	0.9800
N3A—C4A	1.342 (4)	C31X—H3XB	0.9800
C4A—N41A	1.328 (5)	C31X—H3XC	0.9800
C4A—C5A	1.413 (5)	C31X—H3XD	0.9800
N41A—H41A	0.875 (19)	C31X—H3XE	0.9800
N41A—H42A	0.876 (19)	C31X—H3XF	0.9800
C5A—C6A	1.348 (5)	C32X—N3X	1.482 (5)
C5A—H5A	0.9500	C32X—N3X'	1.495 (7)
C6A—H6A	0.9500	C32X—H4XA	0.9800
C1X—N3X'	1.500 (8)	C32X—H4XB	0.9800
C1X—C2X	1.515 (5)	C32X—H4XC	0.9800
C1X—H1XA	0.9800	C32X—H4XD	0.9800
C1X—H1XB	0.9800	C32X—H4XE	0.9800
C1X—H1XC	0.9800	C32X—H4XF	0.9800
C1X—H1XD	0.9800	C2X—N3X	1.328 (5)
C1X—H1XE	0.9800	C2X'—N3X'	1.346 (9)
C6A—N1A—C2A	113.0 (3)	H3XA—C31X—H3XB	109.5
N3A—C2A—N1A	126.7 (3)	N3X—C31X—H3XC	109.5
N3A—C2A—N21A	117.0 (3)	H3XA—C31X—H3XC	109.5
N1A—C2A—N21A	116.3 (3)	H3XB—C31X—H3XC	109.5
C2A—N21A—H21A	112 (2)	C2X'—C31X—H3XD	109.5
C2A—N21A—H22A	120 (2)	C2X'—C31X—H3XE	109.5
H21A—N21A—H22A	128 (3)	H3XD—C31X—H3XE	109.5
C2A—N3A—C4A	117.7 (3)	C2X'—C31X—H3XF	109.5
N41A—C4A—N3A	117.6 (3)	H3XD—C31X—H3XF	109.5
N41A—C4A—C5A	122.4 (3)	H3XE—C31X—H3XF	109.5
N3A—C4A—C5A	120.0 (3)	N3X—C32X—H4XA	109.5
C4A—N41A—H41A	126 (3)	N3X—C32X—H4XB	109.5
C4A—N41A—H42A	123 (3)	H4XA—C32X—H4XB	109.5
H41A—N41A—H42A	110 (4)	N3X—C32X—H4XC	109.5
C6A—C5A—C4A	116.3 (3)	H4XA—C32X—H4XC	109.5
C6A—C5A—H5A	121.8	H4XB—C32X—H4XC	109.5
C4A—C5A—H5A	121.8	N3X'—C32X—H4XD	109.5
N1A—C6A—C5A	126.3 (3)	N3X'—C32X—H4XE	109.5
N1A—C6A—H6A	116.9	H4XD—C32X—H4XE	109.5
C5A—C6A—H6A	116.9	N3X'—C32X—H4XF	109.5
C2X—C1X—H1XA	109.5	H4XD—C32X—H4XF	109.5
C2X—C1X—H1XB	109.5	H4XE—C32X—H4XF	109.5
H1XA—C1X—H1XB	109.5	O21X—C2X—N3X	119.1 (4)
C2X—C1X—H1XC	109.5	O21X—C2X—C1X	124.1 (4)
H1XA—C1X—H1XC	109.5	N3X—C2X—C1X	116.8 (4)
H1XB—C1X—H1XC	109.5	C2X—N3X—C31X	117.6 (3)
N3X'—C1X—H1XD	109.5	C2X—N3X—C32X	120.2 (4)
N3X'—C1X—H1XE	109.5	C31X—N3X—C32X	122.0 (3)
H1XD—C1X—H1XE	109.5	O21X—C2X'—N3X'	114.9 (7)
N3X'—C1X—H1XF	109.5	O21X—C2X'—C31X	132.7 (7)
H1XD—C1X—H1XF	109.5	N3X'—C2X'—C31X	112.4 (6)
H1XE—C1X—H1XF	109.5	C2X'—N3X'—C32X	114.7 (6)
N3X—C31X—H3XA	109.5	C2X'—N3X'—C1X	110.8 (6)
N3X—C31X—H3XB	109.5	C32X—N3X'—C1X	134.5 (7)
C6A—N1A—C2A—N3A	−1.5 (5)	C4A—C5A—C6A—N1A	−0.1 (6)
C6A—N1A—C2A—N21A	178.9 (3)	O21X—C2X—N3X—C31X	−1.0 (6)
N1A—C2A—N3A—C4A	1.4 (5)	C1X—C2X—N3X—C31X	178.2 (4)
N21A—C2A—N3A—C4A	−179.0 (3)	O21X—C2X—N3X—C32X	174.2 (4)
C2A—N3A—C4A—N41A	178.2 (3)	C1X—C2X—N3X—C32X	−6.5 (6)
C2A—N3A—C4A—C5A	−0.5 (5)	O21X—C2X'—N3X'—C32X	−175.0 (11)
N41A—C4A—C5A—C6A	−178.8 (3)	C31X—C2X'—N3X'—C32X	3.2 (18)
N3A—C4A—C5A—C6A	−0.1 (5)	O21X—C2X'—N3X'—C1X	3.9 (19)
C2A—N1A—C6A—C5A	0.8 (5)	C31X—C2X'—N3X'—C1X	−177.8 (10)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···O21X^i	0.90 (2)	2.19 (2)	3.048 (4)	159 (3)
N21A—H22A···N1A^ii	0.90 (2)	2.18 (2)	3.082 (4)	177 (3)
N41A—H41A···N3A^i	0.88 (2)	2.18 (2)	3.055 (4)	175 (3)
N41A—H42A···O21X	0.88 (2)	2.08 (3)	2.845 (4)	145 (3)

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

(IV) Pyrimidine-2,4-diamine–1-methylpyrrolidin-2-one (1/1)

Crystal data

C4H6N4·C5H9NO	F(000) = 896
Mr = 209.26	Dx = 1.324 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.3870 (6) Å	Cell parameters from 16446 reflections
b = 24.8978 (13) Å	θ = 2.4–26.4°
c = 11.5485 (8) Å	µ = 0.09 mm^−1
β = 98.824 (6)°	T = 173 K
V = 2098.9 (3) Å^3	Block, colourless
Z = 8	0.35 × 0.16 × 0.15 mm

Data collection

Stoe IPDS II two-circle diffractometer	3339 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.111
ω scans	θmax = 25.9°, θmin = 2.4°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −8→9
Tmin = 0.194, Tmax = 1.000	k = −30→27
17082 measured reflections	l = −14→14
4062 independent reflections

Refinement

Refinement on F^2	8 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.157	w = 1/[σ^2(Fo^2) + (0.0994P)^2 + 0.1405P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max < 0.001
4062 reflections	Δρmax = 0.36 e Å^−3
297 parameters	Δρmin = −0.25 e Å^−3

Special details

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

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

	x	y	z	Uiso*/Ueq
N1A	0.8466 (2)	0.92283 (6)	0.91180 (12)	0.0395 (3)
C2A	0.7608 (2)	0.88052 (7)	0.85425 (13)	0.0363 (4)
N21A	0.7397 (2)	0.83619 (7)	0.91627 (12)	0.0451 (4)
H21A	0.804 (3)	0.8302 (9)	0.9867 (16)	0.054*
H22A	0.677 (3)	0.8094 (8)	0.8838 (19)	0.054*
N3A	0.69106 (19)	0.87863 (6)	0.73885 (11)	0.0365 (3)
C4A	0.7118 (2)	0.92281 (7)	0.67513 (14)	0.0361 (4)
N41A	0.6440 (2)	0.92058 (7)	0.56008 (12)	0.0440 (4)
H41A	0.591 (3)	0.8903 (8)	0.5304 (19)	0.053*
H42A	0.666 (3)	0.9478 (8)	0.5167 (18)	0.053*
C5A	0.8009 (2)	0.96867 (7)	0.72661 (15)	0.0413 (4)
H5A	0.8168	0.9999	0.6820	0.050*
C6A	0.8640 (2)	0.96610 (7)	0.84460 (15)	0.0410 (4)
H6A	0.9238	0.9968	0.8812	0.049*
N1B	0.5151 (2)	0.74305 (6)	0.82160 (12)	0.0433 (4)
C2B	0.4893 (2)	0.73115 (7)	0.70680 (13)	0.0362 (4)
N21B	0.5265 (2)	0.77089 (7)	0.63497 (13)	0.0451 (4)
H21B	0.563 (3)	0.8036 (7)	0.6624 (19)	0.054*
H22B	0.502 (3)	0.7658 (9)	0.5588 (14)	0.054*
N3B	0.43290 (19)	0.68381 (6)	0.65801 (11)	0.0372 (3)
C4B	0.3932 (2)	0.64481 (7)	0.73086 (14)	0.0378 (4)
N41B	0.3431 (2)	0.59697 (7)	0.68401 (14)	0.0480 (4)
H41B	0.346 (3)	0.5905 (10)	0.6102 (15)	0.058*
H42B	0.307 (3)	0.5704 (8)	0.7274 (19)	0.058*
C5B	0.4067 (3)	0.65426 (8)	0.85183 (14)	0.0439 (4)
H5B	0.3733	0.6277	0.9037	0.053*
C6B	0.4698 (3)	0.70317 (8)	0.89083 (14)	0.0468 (4)
H6B	0.4830	0.7098	0.9727	0.056*
N1X	0.4463 (2)	0.80203 (7)	0.23003 (13)	0.0475 (4)
C11X	0.5109 (3)	0.74788 (9)	0.2514 (2)	0.0595 (5)
H11A	0.5484	0.7425	0.3357	0.089*
H11B	0.6158	0.7416	0.2105	0.089*
H11C	0.4125	0.7226	0.2224	0.089*
C2X	0.4312 (3)	0.83708 (8)	0.31469 (14)	0.0439 (4)
O21X	0.4678 (2)	0.82850 (6)	0.42080 (10)	0.0521 (4)
C3X	0.3605 (3)	0.88984 (8)	0.25974 (16)	0.0488 (4)
H3X1	0.4462	0.9195	0.2863	0.059*
H3X2	0.2389	0.8985	0.2808	0.059*
C4X	0.3473 (3)	0.88132 (10)	0.12855 (18)	0.0593 (6)
H4X1	0.4360	0.9046	0.0961	0.071*
H4X2	0.2225	0.8898	0.0883	0.071*
C5X	0.3916 (3)	0.82237 (9)	0.11235 (15)	0.0532 (5)
H5X1	0.2827	0.8029	0.0725	0.064*
H5X2	0.4923	0.8185	0.0654	0.064*
N1Y	0.20909 (19)	0.44410 (6)	0.73683 (11)	0.0384 (3)
C11Y	0.1258 (3)	0.46997 (8)	0.62969 (14)	0.0455 (4)
H11D	0.0799	0.5054	0.6479	0.068*
H11E	0.0238	0.4480	0.5914	0.068*
H11F	0.2171	0.4741	0.5771	0.068*
C2Y	0.2502 (2)	0.46988 (7)	0.83867 (13)	0.0374 (4)
O21Y	0.22478 (19)	0.51838 (5)	0.85396 (10)	0.0448 (3)
C3Y	0.3332 (3)	0.43090 (8)	0.93077 (15)	0.0442 (4)
H3Y1	0.2573	0.4282	0.9941	0.053*
H3Y2	0.4581	0.4424	0.9653	0.053*
C4Y	0.3393 (3)	0.37713 (8)	0.86795 (16)	0.0476 (4)
H4Y1	0.2642	0.3501	0.9016	0.057*
H4Y2	0.4668	0.3638	0.8753	0.057*
C5Y	0.2616 (3)	0.38793 (8)	0.73922 (16)	0.0444 (4)
H5Y1	0.3554	0.3814	0.6881	0.053*
H5Y2	0.1542	0.3648	0.7131	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0413 (7)	0.0428 (8)	0.0349 (7)	−0.0015 (6)	0.0077 (5)	−0.0021 (5)
C2A	0.0360 (8)	0.0428 (10)	0.0314 (7)	0.0018 (6)	0.0098 (6)	−0.0002 (6)
N21A	0.0599 (10)	0.0451 (9)	0.0290 (7)	−0.0084 (7)	0.0030 (6)	0.0027 (6)
N3A	0.0408 (8)	0.0412 (8)	0.0291 (6)	−0.0008 (6)	0.0102 (5)	0.0005 (5)
C4A	0.0373 (8)	0.0387 (9)	0.0345 (8)	0.0034 (6)	0.0131 (6)	0.0025 (6)
N41A	0.0576 (9)	0.0444 (9)	0.0309 (7)	−0.0049 (7)	0.0093 (6)	0.0037 (6)
C5A	0.0450 (9)	0.0422 (10)	0.0394 (8)	0.0010 (7)	0.0148 (7)	0.0030 (7)
C6A	0.0410 (9)	0.0421 (10)	0.0410 (8)	−0.0020 (7)	0.0101 (7)	−0.0041 (7)
N1B	0.0542 (9)	0.0443 (9)	0.0309 (7)	−0.0021 (7)	0.0050 (6)	0.0018 (6)
C2B	0.0379 (8)	0.0392 (9)	0.0313 (7)	0.0014 (6)	0.0052 (6)	0.0024 (6)
N21B	0.0639 (10)	0.0396 (9)	0.0316 (7)	−0.0057 (7)	0.0067 (6)	0.0032 (6)
N3B	0.0413 (7)	0.0387 (8)	0.0316 (6)	−0.0013 (6)	0.0053 (5)	0.0028 (5)
C4B	0.0364 (8)	0.0412 (9)	0.0354 (8)	0.0001 (7)	0.0040 (6)	0.0041 (6)
N41B	0.0623 (10)	0.0435 (9)	0.0381 (8)	−0.0102 (7)	0.0075 (7)	0.0033 (6)
C5B	0.0522 (10)	0.0460 (10)	0.0340 (8)	−0.0026 (8)	0.0082 (7)	0.0076 (7)
C6B	0.0613 (11)	0.0504 (11)	0.0289 (7)	−0.0005 (8)	0.0073 (7)	0.0024 (7)
N1X	0.0535 (9)	0.0533 (10)	0.0371 (7)	−0.0038 (7)	0.0119 (6)	−0.0024 (6)
C11X	0.0578 (12)	0.0524 (13)	0.0690 (13)	0.0005 (9)	0.0118 (10)	−0.0054 (9)
C2X	0.0463 (10)	0.0525 (11)	0.0343 (8)	−0.0094 (8)	0.0108 (7)	−0.0007 (7)
O21X	0.0698 (9)	0.0574 (9)	0.0291 (6)	−0.0062 (6)	0.0078 (5)	0.0032 (5)
C3X	0.0506 (10)	0.0498 (11)	0.0468 (10)	−0.0055 (8)	0.0096 (8)	0.0019 (8)
C4X	0.0627 (13)	0.0701 (15)	0.0444 (10)	−0.0088 (10)	0.0060 (9)	0.0138 (9)
C5X	0.0593 (12)	0.0712 (14)	0.0317 (8)	−0.0145 (10)	0.0154 (7)	−0.0020 (8)
N1Y	0.0411 (8)	0.0408 (8)	0.0343 (7)	−0.0004 (6)	0.0092 (5)	−0.0017 (5)
C11Y	0.0490 (10)	0.0547 (11)	0.0328 (8)	−0.0027 (8)	0.0067 (7)	−0.0012 (7)
C2Y	0.0393 (8)	0.0419 (10)	0.0335 (7)	−0.0021 (7)	0.0131 (6)	−0.0007 (6)
O21Y	0.0606 (8)	0.0401 (7)	0.0355 (6)	0.0014 (5)	0.0127 (5)	−0.0020 (5)
C3Y	0.0474 (10)	0.0482 (11)	0.0384 (8)	0.0020 (8)	0.0110 (7)	0.0048 (7)
C4Y	0.0496 (10)	0.0429 (11)	0.0517 (10)	0.0004 (8)	0.0123 (8)	0.0050 (7)
C5Y	0.0448 (9)	0.0415 (10)	0.0491 (10)	−0.0025 (7)	0.0141 (7)	−0.0068 (7)

Geometric parameters (Å, º)

N1A—C6A	1.345 (2)	N1X—C5X	1.448 (2)
N1A—C2A	1.350 (2)	C11X—H11A	0.9800
C2A—N21A	1.338 (2)	C11X—H11B	0.9800
C2A—N3A	1.354 (2)	C11X—H11C	0.9800
N21A—H21A	0.891 (16)	C2X—O21X	1.232 (2)
N21A—H22A	0.865 (16)	C2X—C3X	1.516 (3)
N3A—C4A	1.345 (2)	C3X—C4X	1.518 (3)
C4A—N41A	1.347 (2)	C3X—H3X1	0.9900
C4A—C5A	1.404 (2)	C3X—H3X2	0.9900
N41A—H41A	0.893 (16)	C4X—C5X	1.521 (3)
N41A—H42A	0.872 (16)	C4X—H4X1	0.9900
C5A—C6A	1.372 (2)	C4X—H4X2	0.9900
C5A—H5A	0.9500	C5X—H5X1	0.9900
C6A—H6A	0.9500	C5X—H5X2	0.9900
N1B—C2B	1.343 (2)	N1Y—C2Y	1.333 (2)
N1B—C6B	1.349 (2)	N1Y—C11Y	1.446 (2)
C2B—N3B	1.345 (2)	N1Y—C5Y	1.450 (2)
C2B—N21B	1.346 (2)	C11Y—H11D	0.9800
N21B—H21B	0.899 (16)	C11Y—H11E	0.9800
N21B—H22B	0.880 (16)	C11Y—H11F	0.9800
N3B—C4B	1.346 (2)	C2Y—O21Y	1.239 (2)
C4B—N41B	1.337 (2)	C2Y—C3Y	1.500 (2)
C4B—C5B	1.405 (2)	C3Y—C4Y	1.527 (3)
N41B—H41B	0.871 (16)	C3Y—H3Y1	0.9900
N41B—H42B	0.895 (16)	C3Y—H3Y2	0.9900
C5B—C6B	1.356 (3)	C4Y—C5Y	1.533 (3)
C5B—H5B	0.9500	C4Y—H4Y1	0.9900
C6B—H6B	0.9500	C4Y—H4Y2	0.9900
N1X—C2X	1.328 (2)	C5Y—H5Y1	0.9900
N1X—C11X	1.439 (3)	C5Y—H5Y2	0.9900
C6A—N1A—C2A	114.83 (14)	O21X—C2X—C3X	125.11 (17)
N21A—C2A—N1A	117.67 (14)	N1X—C2X—C3X	108.88 (15)
N21A—C2A—N3A	116.13 (15)	C2X—C3X—C4X	105.17 (17)
N1A—C2A—N3A	126.20 (15)	C2X—C3X—H3X1	110.7
C2A—N21A—H21A	122.5 (15)	C4X—C3X—H3X1	110.7
C2A—N21A—H22A	120.2 (15)	C2X—C3X—H3X2	110.7
H21A—N21A—H22A	116 (2)	C4X—C3X—H3X2	110.7
C4A—N3A—C2A	116.87 (15)	H3X1—C3X—H3X2	108.8
N3A—C4A—N41A	116.71 (16)	C3X—C4X—C5X	105.99 (16)
N3A—C4A—C5A	121.26 (15)	C3X—C4X—H4X1	110.5
N41A—C4A—C5A	122.03 (15)	C5X—C4X—H4X1	110.5
C4A—N41A—H41A	119.2 (15)	C3X—C4X—H4X2	110.5
C4A—N41A—H42A	117.5 (15)	C5X—C4X—H4X2	110.5
H41A—N41A—H42A	123 (2)	H4X1—C4X—H4X2	108.7
C6A—C5A—C4A	116.63 (16)	N1X—C5X—C4X	104.84 (15)
C6A—C5A—H5A	121.7	N1X—C5X—H5X1	110.8
C4A—C5A—H5A	121.7	C4X—C5X—H5X1	110.8
N1A—C6A—C5A	124.21 (16)	N1X—C5X—H5X2	110.8
N1A—C6A—H6A	117.9	C4X—C5X—H5X2	110.8
C5A—C6A—H6A	117.9	H5X1—C5X—H5X2	108.9
C2B—N1B—C6B	114.35 (15)	C2Y—N1Y—C11Y	123.35 (16)
N1B—C2B—N3B	126.50 (15)	C2Y—N1Y—C5Y	115.05 (14)
N1B—C2B—N21B	115.76 (16)	C11Y—N1Y—C5Y	121.55 (15)
N3B—C2B—N21B	117.74 (14)	N1Y—C11Y—H11D	109.5
C2B—N21B—H21B	121.7 (14)	N1Y—C11Y—H11E	109.5
C2B—N21B—H22B	118.8 (15)	H11D—C11Y—H11E	109.5
H21B—N21B—H22B	119 (2)	N1Y—C11Y—H11F	109.5
C2B—N3B—C4B	116.97 (14)	H11D—C11Y—H11F	109.5
N41B—C4B—N3B	117.59 (15)	H11E—C11Y—H11F	109.5
N41B—C4B—C5B	121.64 (15)	O21Y—C2Y—N1Y	125.17 (16)
N3B—C4B—C5B	120.77 (16)	O21Y—C2Y—C3Y	125.74 (15)
C4B—N41B—H41B	120.9 (16)	N1Y—C2Y—C3Y	109.09 (15)
C4B—N41B—H42B	121.3 (16)	C2Y—C3Y—C4Y	105.61 (14)
H41B—N41B—H42B	118 (2)	C2Y—C3Y—H3Y1	110.6
C6B—C5B—C4B	116.68 (15)	C4Y—C3Y—H3Y1	110.6
C6B—C5B—H5B	121.7	C2Y—C3Y—H3Y2	110.6
C4B—C5B—H5B	121.7	C4Y—C3Y—H3Y2	110.6
N1B—C6B—C5B	124.61 (15)	H3Y1—C3Y—H3Y2	108.7
N1B—C6B—H6B	117.7	C3Y—C4Y—C5Y	105.85 (15)
C5B—C6B—H6B	117.7	C3Y—C4Y—H4Y1	110.6
C2X—N1X—C11X	123.56 (17)	C5Y—C4Y—H4Y1	110.6
C2X—N1X—C5X	114.72 (18)	C3Y—C4Y—H4Y2	110.6
C11X—N1X—C5X	121.71 (17)	C5Y—C4Y—H4Y2	110.6
N1X—C11X—H11A	109.5	H4Y1—C4Y—H4Y2	108.7
N1X—C11X—H11B	109.5	N1Y—C5Y—C4Y	104.28 (14)
H11A—C11X—H11B	109.5	N1Y—C5Y—H5Y1	110.9
N1X—C11X—H11C	109.5	C4Y—C5Y—H5Y1	110.9
H11A—C11X—H11C	109.5	N1Y—C5Y—H5Y2	110.9
H11B—C11X—H11C	109.5	C4Y—C5Y—H5Y2	110.9
O21X—C2X—N1X	126.01 (19)	H5Y1—C5Y—H5Y2	108.9
C6A—N1A—C2A—N21A	179.82 (15)	C11X—N1X—C2X—O21X	−0.6 (3)
C6A—N1A—C2A—N3A	−1.0 (2)	C5X—N1X—C2X—O21X	179.19 (18)
N21A—C2A—N3A—C4A	−179.73 (15)	C11X—N1X—C2X—C3X	179.55 (18)
N1A—C2A—N3A—C4A	1.1 (2)	C5X—N1X—C2X—C3X	−0.6 (2)
C2A—N3A—C4A—N41A	179.31 (15)	O21X—C2X—C3X—C4X	176.81 (18)
C2A—N3A—C4A—C5A	−0.3 (2)	N1X—C2X—C3X—C4X	−3.4 (2)
N3A—C4A—C5A—C6A	−0.4 (2)	C2X—C3X—C4X—C5X	5.8 (2)
N41A—C4A—C5A—C6A	179.97 (16)	C2X—N1X—C5X—C4X	4.3 (2)
C2A—N1A—C6A—C5A	0.2 (2)	C11X—N1X—C5X—C4X	−175.84 (18)
C4A—C5A—C6A—N1A	0.5 (3)	C3X—C4X—C5X—N1X	−6.1 (2)
C6B—N1B—C2B—N3B	−3.4 (3)	C11Y—N1Y—C2Y—O21Y	−0.8 (3)
C6B—N1B—C2B—N21B	177.51 (16)	C5Y—N1Y—C2Y—O21Y	176.51 (16)
N1B—C2B—N3B—C4B	2.0 (3)	C11Y—N1Y—C2Y—C3Y	179.63 (15)
N21B—C2B—N3B—C4B	−178.87 (15)	C5Y—N1Y—C2Y—C3Y	−3.01 (19)
C2B—N3B—C4B—N41B	−177.74 (16)	O21Y—C2Y—C3Y—C4Y	−178.53 (17)
C2B—N3B—C4B—C5B	1.5 (2)	N1Y—C2Y—C3Y—C4Y	0.99 (19)
N41B—C4B—C5B—C6B	175.99 (18)	C2Y—C3Y—C4Y—C5Y	1.15 (19)
N3B—C4B—C5B—C6B	−3.2 (3)	C2Y—N1Y—C5Y—C4Y	3.65 (19)
C2B—N1B—C6B—C5B	1.3 (3)	C11Y—N1Y—C5Y—C4Y	−178.94 (15)
C4B—C5B—C6B—N1B	1.7 (3)	C3Y—C4Y—C5Y—N1Y	−2.70 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N3B^i	0.89 (2)	2.09 (2)	2.976 (2)	175 (2)
N21A—H22A···N1B	0.87 (2)	2.10 (2)	2.961 (2)	174 (2)
N41A—H41A···O21X	0.89 (2)	2.11 (2)	2.983 (2)	166 (2)
N41A—H42A···O21Y^ii	0.87 (2)	2.16 (2)	2.9610 (19)	152 (2)
N21B—H21B···N3A	0.90 (2)	2.22 (2)	3.109 (2)	172 (2)
N21B—H22B···O21X	0.88 (2)	2.22 (2)	2.8344 (19)	127 (2)
N41B—H41B···N1A^iii	0.87 (2)	2.32 (2)	3.186 (2)	177 (2)
N41B—H42B···O21Y	0.90 (2)	2.11 (2)	2.995 (2)	170 (2)

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

(V) 2,4-Diaminopyrimidinium 2,4,6-trioxopyrimidin-5-ide

Crystal data

C4H7N4^+·C4H3N2O3^−	F(000) = 496
Mr = 238.22	Dx = 1.568 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 4.6822 (7) Å	Cell parameters from 5705 reflections
b = 15.948 (3) Å	θ = 3.8–26.2°
c = 13.514 (2) Å	µ = 0.12 mm^−1
β = 90.240 (13)°	T = 173 K
V = 1009.1 (3) Å^3	Block, colourless
Z = 4	0.20 × 0.10 × 0.08 mm

Data collection

Stoe IPDS II two-circle diffractometer	1460 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.102
ω scans	θmax = 25.9°, θmin = 3.8°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −5→5
Tmin = 0.619, Tmax = 1.000	k = −19→18
7860 measured reflections	l = −16→16
1944 independent reflections

Refinement

Refinement on F^2	7 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.097	w = 1/[σ^2(Fo^2) + (0.036P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
1944 reflections	Δρmax = 0.23 e Å^−3
176 parameters	Δρmin = −0.25 e Å^−3

Special details

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

Refinement. Refined as a 2-component twin.

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

	x	y	z	Uiso*/Ueq
N1A	0.2689 (7)	0.42819 (16)	0.44519 (19)	0.0169 (6)
H1A	0.222 (8)	0.4549 (18)	0.4994 (19)	0.020*
C2A	0.4877 (8)	0.37155 (17)	0.4487 (2)	0.0163 (7)
O21A	0.6357 (6)	0.35884 (12)	0.52379 (16)	0.0223 (5)
N3A	0.5357 (7)	0.32902 (14)	0.36289 (19)	0.0178 (6)
H3A	0.671 (6)	0.2912 (16)	0.370 (3)	0.021*
C4A	0.3840 (8)	0.34092 (18)	0.2746 (2)	0.0183 (7)
O41A	0.4528 (6)	0.29552 (13)	0.20251 (16)	0.0258 (6)
C5A	0.1670 (8)	0.40157 (19)	0.2754 (2)	0.0183 (7)
H5A	0.0632	0.4133	0.2164	0.022*
C6A	0.1031 (7)	0.44454 (16)	0.3619 (2)	0.0160 (7)
O61A	−0.0959 (5)	0.49829 (11)	0.37188 (16)	0.0189 (5)
N1B	1.1948 (7)	0.08187 (16)	0.2962 (2)	0.0214 (7)
H1B	1.208 (9)	0.0502 (19)	0.2416 (19)	0.026*
C2B	1.0026 (7)	0.14533 (16)	0.2973 (2)	0.0176 (7)
N21B	0.8403 (7)	0.15692 (17)	0.2181 (2)	0.0236 (7)
H22B	0.709 (7)	0.1965 (18)	0.220 (3)	0.028*
H21B	0.870 (9)	0.1269 (18)	0.1649 (18)	0.028*
N3B	0.9683 (6)	0.19526 (14)	0.37599 (19)	0.0186 (6)
C4B	1.1312 (8)	0.18093 (17)	0.4576 (2)	0.0176 (7)
N41B	1.0845 (7)	0.22811 (15)	0.53618 (19)	0.0233 (7)
H41B	0.970 (7)	0.2709 (16)	0.533 (3)	0.028*
H42B	1.176 (8)	0.221 (2)	0.5918 (19)	0.028*
C5B	1.3433 (8)	0.11656 (17)	0.4593 (2)	0.0234 (7)
H5B	1.4624	0.1078	0.5155	0.028*
C6B	1.3665 (8)	0.06878 (17)	0.3771 (3)	0.0234 (7)
H6B	1.5048	0.0252	0.3754	0.028*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0209 (16)	0.0194 (13)	0.0105 (12)	0.0029 (11)	0.0017 (11)	−0.0022 (10)
C2A	0.0199 (18)	0.0155 (13)	0.0133 (15)	−0.0058 (13)	−0.0004 (14)	0.0031 (10)
O21A	0.0251 (14)	0.0274 (11)	0.0144 (11)	0.0042 (10)	−0.0093 (12)	−0.0032 (9)
N3A	0.0196 (16)	0.0188 (11)	0.0150 (12)	0.0041 (11)	−0.0056 (13)	−0.0028 (10)
C4A	0.0201 (18)	0.0223 (15)	0.0126 (14)	−0.0020 (14)	−0.0039 (14)	0.0001 (11)
O41A	0.0294 (15)	0.0325 (11)	0.0155 (10)	0.0109 (11)	−0.0088 (11)	−0.0091 (9)
C5A	0.0174 (18)	0.0217 (14)	0.0157 (14)	0.0026 (13)	−0.0033 (15)	−0.0006 (12)
C6A	0.0166 (18)	0.0135 (12)	0.0180 (15)	−0.0017 (12)	−0.0032 (15)	0.0025 (11)
O61A	0.0240 (13)	0.0172 (9)	0.0154 (10)	0.0052 (10)	−0.0018 (11)	0.0010 (8)
N1B	0.0271 (18)	0.0201 (13)	0.0170 (14)	0.0005 (12)	−0.0013 (13)	−0.0023 (11)
C2B	0.0211 (19)	0.0165 (13)	0.0153 (14)	−0.0017 (13)	0.0025 (15)	0.0003 (11)
N21B	0.0296 (19)	0.0264 (14)	0.0146 (13)	0.0056 (13)	−0.0050 (14)	−0.0051 (11)
N3B	0.0207 (17)	0.0207 (12)	0.0143 (12)	−0.0012 (11)	−0.0008 (14)	−0.0002 (11)
C4B	0.0206 (19)	0.0176 (13)	0.0146 (15)	−0.0060 (13)	−0.0034 (15)	0.0049 (11)
N41B	0.0323 (19)	0.0226 (13)	0.0150 (12)	0.0048 (12)	−0.0071 (14)	−0.0002 (11)
C5B	0.0254 (19)	0.0235 (15)	0.0212 (17)	0.0002 (15)	−0.0058 (17)	0.0048 (13)
C6B	0.0218 (18)	0.0213 (14)	0.0269 (17)	0.0048 (14)	−0.0046 (18)	0.0035 (14)

Geometric parameters (Å, º)

N1A—C2A	1.366 (4)	N1B—H1B	0.896 (18)
N1A—C6A	1.390 (4)	C2B—N21B	1.323 (4)
N1A—H1A	0.878 (18)	C2B—N3B	1.339 (4)
C2A—O21A	1.243 (4)	N21B—H22B	0.881 (19)
C2A—N3A	1.363 (4)	N21B—H21B	0.875 (18)
N3A—C4A	1.399 (4)	N3B—C4B	1.358 (4)
N3A—H3A	0.879 (18)	C4B—N41B	1.320 (4)
C4A—O41A	1.257 (4)	C4B—C5B	1.428 (5)
C4A—C5A	1.403 (5)	N41B—H41B	0.868 (18)
C5A—C6A	1.389 (4)	N41B—H42B	0.870 (19)
C5A—H5A	0.9500	C5B—C6B	1.352 (5)
C6A—O61A	1.274 (4)	C5B—H5B	0.9500
N1B—C2B	1.354 (4)	C6B—H6B	0.9500
N1B—C6B	1.371 (5)
C2A—N1A—C6A	124.7 (3)	C6B—N1B—H1B	122 (2)
C2A—N1A—H1A	119 (2)	N21B—C2B—N3B	119.3 (3)
C6A—N1A—H1A	116 (2)	N21B—C2B—N1B	118.3 (3)
O21A—C2A—N3A	121.3 (3)	N3B—C2B—N1B	122.3 (3)
O21A—C2A—N1A	123.5 (3)	C2B—N21B—H22B	119 (2)
N3A—C2A—N1A	115.2 (3)	C2B—N21B—H21B	120 (3)
C2A—N3A—C4A	125.0 (3)	H22B—N21B—H21B	122 (4)
C2A—N3A—H3A	112 (2)	C2B—N3B—C4B	118.5 (3)
C4A—N3A—H3A	123 (2)	N41B—C4B—N3B	117.6 (3)
O41A—C4A—N3A	116.9 (3)	N41B—C4B—C5B	121.0 (3)
O41A—C4A—C5A	126.2 (3)	N3B—C4B—C5B	121.5 (3)
N3A—C4A—C5A	116.9 (3)	C4B—N41B—H41B	121 (2)
C6A—C5A—C4A	120.3 (3)	C4B—N41B—H42B	123 (2)
C6A—C5A—H5A	119.8	H41B—N41B—H42B	116 (3)
C4A—C5A—H5A	119.8	C6B—C5B—C4B	116.8 (3)
O61A—C6A—C5A	125.6 (3)	C6B—C5B—H5B	121.6
O61A—C6A—N1A	116.5 (3)	C4B—C5B—H5B	121.6
C5A—C6A—N1A	117.9 (3)	C5B—C6B—N1B	121.4 (3)
C2B—N1B—C6B	119.5 (3)	C5B—C6B—H6B	119.3
C2B—N1B—H1B	119 (2)	N1B—C6B—H6B	119.3
C6A—N1A—C2A—O21A	179.0 (3)	C2A—N1A—C6A—C5A	−1.3 (4)
C6A—N1A—C2A—N3A	−0.8 (4)	C6B—N1B—C2B—N21B	179.7 (3)
O21A—C2A—N3A—C4A	−178.4 (3)	C6B—N1B—C2B—N3B	−1.6 (5)
N1A—C2A—N3A—C4A	1.4 (4)	N21B—C2B—N3B—C4B	178.2 (3)
C2A—N3A—C4A—O41A	−179.0 (3)	N1B—C2B—N3B—C4B	−0.6 (5)
C2A—N3A—C4A—C5A	0.2 (5)	C2B—N3B—C4B—N41B	−176.7 (3)
O41A—C4A—C5A—C6A	176.7 (3)	C2B—N3B—C4B—C5B	2.6 (5)
N3A—C4A—C5A—C6A	−2.4 (5)	N41B—C4B—C5B—C6B	176.9 (3)
C4A—C5A—C6A—O61A	−177.1 (3)	N3B—C4B—C5B—C6B	−2.4 (5)
C4A—C5A—C6A—N1A	2.9 (5)	C4B—C5B—C6B—N1B	0.2 (5)
C2A—N1A—C6A—O61A	178.8 (3)	C2B—N1B—C6B—C5B	1.7 (5)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O61A^i	0.88 (2)	1.98 (2)	2.856 (3)	173 (3)
N3A—H3A···N3B	0.88 (2)	2.07 (2)	2.946 (4)	175 (3)
N1B—H1B···O61A^ii	0.90 (2)	1.82 (2)	2.672 (3)	159 (4)
N21B—H22B···O41A	0.88 (2)	2.00 (2)	2.867 (4)	169 (4)
N21B—H21B···O21A^iii	0.88 (2)	2.21 (3)	2.803 (3)	125 (3)
N21B—H21B···O61A^ii	0.88 (2)	2.36 (3)	3.053 (3)	136 (3)
N41B—H41B···O21A	0.87 (2)	2.11 (2)	2.965 (4)	170 (3)
N41B—H42B···O41A^iv	0.87 (2)	1.99 (2)	2.852 (4)	169 (4)

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

(VI) 2,4-Diaminopyrimidinium 4,6-dioxo-2-sulfanylidenepyrimidin-5-ide–N,N-dimethylformamide (1/2)

Crystal data

C4H7N4^+·C4H3N2O2S^−·2C3H7NO	F(000) = 848
Mr = 400.47	Dx = 1.334 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.0115 (9) Å	Cell parameters from 20088 reflections
b = 19.2213 (14) Å	θ = 3.3–26.3°
c = 12.9531 (13) Å	µ = 0.20 mm^−1
β = 90.230 (8)°	T = 173 K
V = 1994.7 (3) Å^3	Plate, yellow
Z = 4	0.39 × 0.28 × 0.15 mm

Data collection

Stoe IPDS II two-circle diffractometer	3134 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.048
ω scans	θmax = 25.9°, θmin = 3.3°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −9→9
Tmin = 0.532, Tmax = 1.000	k = −23→19
14897 measured reflections	l = −15→15
3834 independent reflections

Refinement

Refinement on F^2	114 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.104	w = 1/[σ^2(Fo^2) + (0.050P)^2 + 0.7095P] where P = (Fo^2 + 2Fc^2)/3
S = 1.04	(Δ/σ)max = 0.040
3834 reflections	Δρmax = 0.34 e Å^−3
282 parameters	Δρmin = −0.27 e Å^−3

Special details

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

Refinement. The used target distances were 1.23 (1) Å for d(C1Y,O11Y) and d(C1Y',O11Y), 1.32 (1) Å for d(C1Y,N2Y) and d(C1Y',N2Y), 1.44 (1) Å for d(N2Y,C3Y) and d(N2Y,C4Y), 1.44 (1) Å for d(N2Y,C3Y') and d(N2Y,C4Y'), 2.26 (2) Å for d(O11Y,N2Y), 2.41 (2) Å for d(C1Y,C3Y) and d(C1Y',C3Y'), 2.47 (2) Å for d(C3Y,C4Y) and d(C3Y',C4Y'), 2.41 (2) Å for d(C1Y,C4Y) and d(C1Y',C4Y').

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.84760 (19)	0.06939 (7)	0.46165 (11)	0.0250 (3)
H1A	0.887 (2)	0.0500 (10)	0.5165 (13)	0.030*
C2A	0.7540 (2)	0.12707 (9)	0.47481 (13)	0.0249 (4)
S21A	0.69289 (7)	0.15336 (3)	0.59188 (3)	0.03891 (16)
N3A	0.71165 (18)	0.16090 (7)	0.38694 (10)	0.0240 (3)
H3A	0.658 (2)	0.1997 (9)	0.3925 (15)	0.029*
C4A	0.7587 (2)	0.14054 (9)	0.28742 (13)	0.0246 (4)
O41A	0.70990 (17)	0.17795 (7)	0.21384 (9)	0.0340 (3)
C5A	0.8541 (2)	0.08030 (9)	0.27958 (13)	0.0259 (4)
H5A	0.8861	0.0638	0.2134	0.031*
C6A	0.9028 (2)	0.04408 (8)	0.36688 (12)	0.0238 (4)
O61A	0.99171 (16)	−0.01030 (6)	0.36919 (9)	0.0304 (3)
N1B	0.47285 (19)	0.40827 (8)	0.30032 (11)	0.0276 (3)
H1B	0.484 (3)	0.4335 (10)	0.2430 (13)	0.033*
C2B	0.5347 (2)	0.34282 (9)	0.30336 (13)	0.0249 (4)
N21B	0.6095 (2)	0.31781 (9)	0.22048 (12)	0.0338 (4)
H21B	0.604 (3)	0.3400 (11)	0.1640 (14)	0.041*
H22B	0.639 (3)	0.2730 (9)	0.2203 (16)	0.041*
N3B	0.52452 (18)	0.30284 (7)	0.38770 (10)	0.0243 (3)
C4B	0.4433 (2)	0.32879 (9)	0.47022 (13)	0.0247 (4)
N41B	0.4331 (2)	0.28982 (8)	0.55359 (12)	0.0341 (4)
H41B	0.483 (3)	0.2483 (9)	0.5548 (16)	0.041*
H42B	0.368 (2)	0.3027 (12)	0.6052 (14)	0.041*
C5B	0.3710 (2)	0.39653 (9)	0.46897 (13)	0.0283 (4)
H5B	0.3113	0.4139	0.5267	0.034*
C6B	0.3906 (2)	0.43480 (9)	0.38325 (13)	0.0289 (4)
H6B	0.3467	0.4807	0.3804	0.035*
C1X	0.7561 (3)	0.38746 (12)	−0.02899 (17)	0.0453 (5)
H1X	0.7859	0.4241	0.0167	0.054*
O11X	0.6752 (2)	0.34008 (9)	0.00683 (12)	0.0541 (4)
N2X	0.8070 (2)	0.39296 (9)	−0.12613 (13)	0.0420 (4)
C3X	0.7669 (3)	0.34004 (14)	−0.20127 (18)	0.0550 (6)
H3X1	0.7095	0.3014	−0.1671	0.082*
H3X2	0.8700	0.3230	−0.2330	0.082*
H3X3	0.6942	0.3598	−0.2547	0.082*
C4X	0.8879 (3)	0.45554 (14)	−0.1627 (2)	0.0636 (7)
H4X1	0.8099	0.4820	−0.2060	0.095*
H4X2	0.9863	0.4429	−0.2034	0.095*
H4X3	0.9223	0.4840	−0.1036	0.095*
O11Y	0.2006 (3)	0.57184 (11)	0.44309 (18)	0.0870 (7)
N2Y	0.0745 (2)	0.62769 (9)	0.57514 (14)	0.0425 (4)
C1Y	0.1367 (4)	0.62427 (14)	0.4809 (2)	0.0565 (8)	0.902 (4)
H1YA	0.1318	0.6650	0.4395	0.068*	0.902 (4)
C3Y	0.0797 (4)	0.56662 (14)	0.6413 (2)	0.0602 (8)	0.902 (4)
H3YA	0.0943	0.5812	0.7133	0.090*	0.902 (4)
H3YB	0.1733	0.5368	0.6210	0.090*	0.902 (4)
H3YC	−0.0250	0.5407	0.6342	0.090*	0.902 (4)
C4Y	0.0042 (3)	0.69037 (14)	0.6167 (2)	0.0546 (8)	0.902 (4)
H4YA	−0.1104	0.6814	0.6393	0.082*	0.902 (4)
H4YB	0.0035	0.7266	0.5635	0.082*	0.902 (4)
H4YC	0.0714	0.7059	0.6757	0.082*	0.902 (4)
C1Y'	0.146 (4)	0.5708 (8)	0.5355 (12)	0.087 (8)*	0.098 (4)
H1YB	0.1550	0.5297	0.5759	0.104*	0.098 (4)
C3Y'	0.065 (3)	0.6836 (9)	0.4975 (14)	0.059 (7)*	0.098 (4)
H3YD	0.0123	0.7248	0.5282	0.089*	0.098 (4)
H3YE	0.1774	0.6955	0.4742	0.089*	0.098 (4)
H3YF	−0.0022	0.6678	0.4385	0.089*	0.098 (4)
C4Y'	0.008 (4)	0.6444 (13)	0.6742 (12)	0.069 (8)*	0.098 (4)
H4YD	−0.0338	0.6923	0.6736	0.103*	0.098 (4)
H4YE	−0.0830	0.6124	0.6905	0.103*	0.098 (4)
H4YF	0.0964	0.6400	0.7265	0.103*	0.098 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0344 (8)	0.0210 (7)	0.0197 (7)	0.0058 (6)	−0.0031 (6)	−0.0008 (6)
C2A	0.0293 (9)	0.0225 (8)	0.0229 (8)	0.0007 (7)	−0.0005 (7)	−0.0008 (6)
S21A	0.0580 (3)	0.0383 (3)	0.0205 (2)	0.0229 (2)	0.0014 (2)	−0.00117 (19)
N3A	0.0305 (8)	0.0199 (7)	0.0217 (7)	0.0052 (6)	0.0021 (6)	0.0000 (6)
C4A	0.0275 (9)	0.0225 (8)	0.0237 (8)	−0.0015 (7)	0.0024 (6)	0.0011 (6)
O41A	0.0462 (8)	0.0326 (7)	0.0233 (6)	0.0123 (6)	0.0063 (5)	0.0072 (5)
C5A	0.0318 (9)	0.0257 (9)	0.0203 (8)	0.0018 (7)	0.0015 (7)	−0.0022 (6)
C6A	0.0266 (8)	0.0199 (8)	0.0249 (8)	−0.0015 (7)	−0.0014 (7)	−0.0049 (6)
O61A	0.0422 (7)	0.0231 (6)	0.0257 (6)	0.0106 (5)	−0.0039 (5)	−0.0051 (5)
N1B	0.0359 (8)	0.0220 (7)	0.0250 (7)	0.0009 (6)	−0.0017 (6)	0.0065 (6)
C2B	0.0274 (9)	0.0227 (8)	0.0245 (8)	−0.0009 (7)	−0.0024 (7)	0.0034 (7)
N21B	0.0477 (10)	0.0317 (8)	0.0219 (8)	0.0092 (7)	0.0047 (7)	0.0082 (6)
N3B	0.0305 (8)	0.0212 (7)	0.0212 (7)	0.0017 (6)	0.0017 (6)	0.0033 (5)
C4B	0.0265 (9)	0.0239 (9)	0.0235 (8)	−0.0020 (7)	−0.0013 (7)	−0.0002 (6)
N41B	0.0507 (10)	0.0259 (8)	0.0257 (8)	0.0082 (7)	0.0114 (7)	0.0047 (6)
C5B	0.0330 (10)	0.0261 (9)	0.0259 (9)	0.0031 (7)	−0.0017 (7)	−0.0026 (7)
C6B	0.0335 (10)	0.0219 (8)	0.0312 (9)	0.0034 (7)	−0.0055 (7)	−0.0006 (7)
C1X	0.0461 (12)	0.0441 (12)	0.0457 (12)	0.0153 (10)	0.0051 (10)	0.0086 (10)
O11X	0.0689 (11)	0.0520 (10)	0.0415 (8)	0.0114 (8)	0.0155 (8)	0.0144 (7)
N2X	0.0403 (10)	0.0424 (10)	0.0435 (10)	0.0089 (8)	0.0092 (8)	0.0147 (8)
C3X	0.0560 (14)	0.0669 (16)	0.0422 (12)	0.0088 (12)	0.0088 (11)	0.0061 (11)
C4X	0.0484 (14)	0.0516 (15)	0.091 (2)	0.0097 (11)	0.0206 (13)	0.0292 (14)
O11Y	0.0957 (16)	0.0649 (13)	0.1006 (17)	0.0171 (12)	0.0210 (13)	−0.0269 (12)
N2Y	0.0417 (10)	0.0312 (9)	0.0545 (11)	−0.0006 (8)	−0.0005 (8)	−0.0008 (8)
C1Y	0.0630 (17)	0.0415 (15)	0.0651 (17)	0.0014 (13)	0.0042 (14)	0.0002 (13)
C3Y	0.0608 (18)	0.0425 (15)	0.077 (2)	−0.0091 (13)	−0.0137 (15)	0.0113 (13)
C4Y	0.0458 (15)	0.0431 (15)	0.0750 (19)	0.0024 (11)	−0.0063 (13)	−0.0164 (13)

Geometric parameters (Å, º)

N1A—C2A	1.350 (2)	N2X—C3X	1.443 (3)
N1A—C6A	1.394 (2)	N2X—C4X	1.447 (3)
N1A—H1A	0.862 (15)	C3X—H3X1	0.9800
C2A—N3A	1.353 (2)	C3X—H3X2	0.9800
C2A—S21A	1.6736 (17)	C3X—H3X3	0.9800
N3A—C4A	1.400 (2)	C4X—H4X1	0.9800
N3A—H3A	0.864 (15)	C4X—H4X2	0.9800
C4A—O41A	1.255 (2)	C4X—H4X3	0.9800
C4A—C5A	1.391 (2)	O11Y—C1Y	1.233 (3)
C5A—C6A	1.383 (2)	O11Y—C1Y'	1.277 (10)
C5A—H5A	0.9500	N2Y—C1Y	1.322 (3)
C6A—O61A	1.265 (2)	N2Y—C1Y'	1.337 (9)
N1B—C2B	1.352 (2)	N2Y—C4Y'	1.427 (9)
N1B—C6B	1.362 (2)	N2Y—C4Y	1.436 (3)
N1B—H1B	0.892 (15)	N2Y—C3Y	1.454 (3)
C2B—N21B	1.322 (2)	N2Y—C3Y'	1.475 (9)
C2B—N3B	1.339 (2)	C1Y—H1YA	0.9500
N21B—H21B	0.848 (16)	C3Y—H3YA	0.9800
N21B—H22B	0.894 (16)	C3Y—H3YB	0.9800
N3B—C4B	1.349 (2)	C3Y—H3YC	0.9800
C4B—N41B	1.317 (2)	C4Y—H4YA	0.9800
C4B—C5B	1.425 (2)	C4Y—H4YB	0.9800
N41B—H41B	0.892 (16)	C4Y—H4YC	0.9800
N41B—H42B	0.885 (16)	C1Y'—H1YB	0.9500
C5B—C6B	1.342 (2)	C3Y'—H3YD	0.9800
C5B—H5B	0.9500	C3Y'—H3YE	0.9800
C6B—H6B	0.9500	C3Y'—H3YF	0.9800
C1X—O11X	1.211 (3)	C4Y'—H4YD	0.9800
C1X—N2X	1.328 (3)	C4Y'—H4YE	0.9800
C1X—H1X	0.9500	C4Y'—H4YF	0.9800
C2A—N1A—C6A	125.19 (14)	N2X—C3X—H3X2	109.5
C2A—N1A—H1A	116.9 (13)	H3X1—C3X—H3X2	109.5
C6A—N1A—H1A	117.3 (13)	N2X—C3X—H3X3	109.5
N1A—C2A—N3A	115.23 (15)	H3X1—C3X—H3X3	109.5
N1A—C2A—S21A	121.82 (13)	H3X2—C3X—H3X3	109.5
N3A—C2A—S21A	122.94 (13)	N2X—C4X—H4X1	109.5
C2A—N3A—C4A	124.92 (15)	N2X—C4X—H4X2	109.5
C2A—N3A—H3A	117.9 (13)	H4X1—C4X—H4X2	109.5
C4A—N3A—H3A	117.0 (13)	N2X—C4X—H4X3	109.5
O41A—C4A—C5A	126.22 (16)	H4X1—C4X—H4X3	109.5
O41A—C4A—N3A	117.05 (15)	H4X2—C4X—H4X3	109.5
C5A—C4A—N3A	116.73 (15)	C1Y'—N2Y—C4Y'	133.6 (11)
C6A—C5A—C4A	120.84 (15)	C1Y—N2Y—C4Y	122.5 (2)
C6A—C5A—H5A	119.6	C1Y—N2Y—C3Y	119.6 (2)
C4A—C5A—H5A	119.6	C4Y—N2Y—C3Y	117.8 (2)
O61A—C6A—C5A	126.33 (15)	C1Y'—N2Y—C3Y'	110.9 (9)
O61A—C6A—N1A	116.62 (14)	C4Y'—N2Y—C3Y'	115.5 (11)
C5A—C6A—N1A	117.04 (15)	O11Y—C1Y—N2Y	124.5 (3)
C2B—N1B—C6B	120.25 (15)	O11Y—C1Y—H1YA	117.8
C2B—N1B—H1B	119.5 (13)	N2Y—C1Y—H1YA	117.8
C6B—N1B—H1B	120.2 (13)	N2Y—C3Y—H3YA	109.5
N21B—C2B—N3B	118.90 (16)	N2Y—C3Y—H3YB	109.5
N21B—C2B—N1B	118.80 (15)	H3YA—C3Y—H3YB	109.5
N3B—C2B—N1B	122.30 (15)	N2Y—C3Y—H3YC	109.5
C2B—N21B—H21B	119.7 (15)	H3YA—C3Y—H3YC	109.5
C2B—N21B—H22B	118.3 (14)	H3YB—C3Y—H3YC	109.5
H21B—N21B—H22B	120 (2)	N2Y—C4Y—H4YA	109.5
C2B—N3B—C4B	117.74 (15)	N2Y—C4Y—H4YB	109.5
N41B—C4B—N3B	118.10 (16)	H4YA—C4Y—H4YB	109.5
N41B—C4B—C5B	120.15 (16)	N2Y—C4Y—H4YC	109.5
N3B—C4B—C5B	121.74 (15)	H4YA—C4Y—H4YC	109.5
C4B—N41B—H41B	119.6 (14)	H4YB—C4Y—H4YC	109.5
C4B—N41B—H42B	119.9 (15)	O11Y—C1Y'—N2Y	119.8 (10)
H41B—N41B—H42B	120 (2)	O11Y—C1Y'—H1YB	120.1
C6B—C5B—C4B	117.49 (16)	N2Y—C1Y'—H1YB	120.1
C6B—C5B—H5B	121.3	N2Y—C3Y'—H3YD	109.5
C4B—C5B—H5B	121.3	N2Y—C3Y'—H3YE	109.5
C5B—C6B—N1B	120.40 (16)	H3YD—C3Y'—H3YE	109.5
C5B—C6B—H6B	119.8	N2Y—C3Y'—H3YF	109.5
N1B—C6B—H6B	119.8	H3YD—C3Y'—H3YF	109.5
O11X—C1X—N2X	126.1 (2)	H3YE—C3Y'—H3YF	109.5
O11X—C1X—H1X	116.9	N2Y—C4Y'—H4YD	109.5
N2X—C1X—H1X	116.9	N2Y—C4Y'—H4YE	109.5
C1X—N2X—C3X	120.97 (19)	H4YD—C4Y'—H4YE	109.5
C1X—N2X—C4X	121.1 (2)	N2Y—C4Y'—H4YF	109.5
C3X—N2X—C4X	117.6 (2)	H4YD—C4Y'—H4YF	109.5
N2X—C3X—H3X1	109.5	H4YE—C4Y'—H4YF	109.5
C6A—N1A—C2A—N3A	0.9 (2)	N21B—C2B—N3B—C4B	−178.11 (16)
C6A—N1A—C2A—S21A	179.78 (13)	N1B—C2B—N3B—C4B	2.7 (2)
N1A—C2A—N3A—C4A	−0.5 (2)	C2B—N3B—C4B—N41B	−179.85 (16)
S21A—C2A—N3A—C4A	−179.45 (13)	C2B—N3B—C4B—C5B	−0.4 (2)
C2A—N3A—C4A—O41A	−179.52 (16)	N41B—C4B—C5B—C6B	177.64 (17)
C2A—N3A—C4A—C5A	1.0 (2)	N3B—C4B—C5B—C6B	−1.8 (3)
O41A—C4A—C5A—C6A	178.82 (17)	C4B—C5B—C6B—N1B	1.7 (3)
N3A—C4A—C5A—C6A	−1.8 (2)	C2B—N1B—C6B—C5B	0.5 (3)
C4A—C5A—C6A—O61A	−178.62 (17)	O11X—C1X—N2X—C3X	0.3 (3)
C4A—C5A—C6A—N1A	2.1 (2)	O11X—C1X—N2X—C4X	173.4 (2)
C2A—N1A—C6A—O61A	178.99 (16)	C4Y—N2Y—C1Y—O11Y	178.7 (3)
C2A—N1A—C6A—C5A	−1.6 (3)	C3Y—N2Y—C1Y—O11Y	0.1 (4)
C6B—N1B—C2B—N21B	177.99 (16)	C4Y'—N2Y—C1Y'—O11Y	−177 (2)
C6B—N1B—C2B—N3B	−2.8 (3)	C3Y'—N2Y—C1Y'—O11Y	3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N3A—H3A···N3B	0.86 (2)	2.25 (2)	3.113 (2)	173 (2)
N1A—H1A···O61A^i	0.86 (2)	1.93 (2)	2.7795 (19)	171 (2)
N1B—H1B···O61A^ii	0.89 (2)	1.82 (2)	2.7123 (18)	177 (2)
N21B—H21B···O11X	0.85 (2)	2.12 (2)	2.851 (2)	145 (2)
N21B—H22B···O41A	0.89 (2)	1.92 (2)	2.807 (2)	177 (2)
N41B—H41B···S21A	0.89 (2)	2.53 (2)	3.3839 (17)	161 (2)
N41B—H42B···O41A^iii	0.89 (2)	1.93 (2)	2.814 (2)	173 (2)
C6B—H6B···O11Y	0.95	2.26	3.141 (3)	154

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

(VII) 2,4-Diaminopyrimidinium 4,6-dioxo-2-sulfanylidene–N,N-dimethylacetamide (1/2)

Crystal data

C4H7N4^+·C4H3N2O2S^−·2(C4H9NO)	F(000) = 912
Mr = 428.52	Dx = 1.300 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.8868 (12) Å	Cell parameters from 12893 reflections
b = 17.2380 (14) Å	θ = 3.4–25.9°
c = 12.8571 (14) Å	µ = 0.19 mm^−1
β = 88.151 (9)°	T = 173 K
V = 2190.1 (4) Å^3	Block, yellow
Z = 4	0.18 × 0.11 × 0.08 mm

Data collection

Stoe IPDS II two-circle diffractometer	2955 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	Rint = 0.059
ω scans	θmax = 25.9°, θmin = 3.5°
Absorption correction: multi-scan (X-AREA; Stoe & Cie, 2001)	h = −10→12
Tmin = 0.653, Tmax = 1.000	k = −20→21
17989 measured reflections	l = −15→15
4205 independent reflections

Refinement

Refinement on F^2	135 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.103	w = 1/[σ^2(Fo^2) + (0.0514P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.98	(Δ/σ)max = 0.001
4205 reflections	Δρmax = 0.21 e Å^−3
308 parameters	Δρmin = −0.19 e Å^−3

Special details

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

Refinement. The used target distances were 1.52 (1) Å for d(C1X/Y,C2X/Y) and d(C31X/Y,C2X'/Y'), 1.25 (1) Å for d(C2X/Y,O21X/Y) and d(C2X'/Y',O21X/Y), 1.30 (1) Å for d(C2X/Y,N3X/Y) and d(C2X'/Y',N3X'/Y'), 1.47 (1) Å for d(N3X/Y,C31X/Y), d(N3X/Y,C32X/Y), d(N3X'/Y',C1X/Y) and d(N3X'/Y',C32X/Y), 2.42 (2) Å for d(O21X/Y,C1X/Y) and d(O21X/Y,C31X/Y), 2.23 (2) Å for d(O21X/Y,N3X/Y) and d(O21X/Y,N3X'/Y'), 2.41 (2) Å for d(C1X/Y,N3X/Y) and d(C31X/Y,N3X'/Y'), 2.41 (2) Å for d(C2X/Y,C31X/Y) and d(C2X'/Y',C1X/Y), 2.43 (2) Å for d(C2X/Y,C32X/Y) and d(C2X'/Y',C32X/Y), and 2.52 (2) Å for d(C31X/Y,C32X/Y) and d(C1X/Y,C32X/Y).

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.88288 (18)	0.07520 (10)	0.45962 (12)	0.0269 (4)
H1A	0.908 (2)	0.0492 (12)	0.5114 (15)	0.032*
C2A	0.7891 (2)	0.13066 (12)	0.47308 (15)	0.0263 (5)
S21A	0.71829 (6)	0.14897 (4)	0.59124 (4)	0.03585 (17)
N3A	0.75454 (18)	0.16903 (11)	0.38638 (12)	0.0281 (4)
H3A	0.691 (2)	0.2043 (12)	0.3917 (17)	0.034*
C4A	0.8082 (2)	0.15380 (13)	0.28639 (14)	0.0292 (5)
O41A	0.76665 (16)	0.19478 (10)	0.21302 (10)	0.0383 (4)
C5A	0.9035 (2)	0.09471 (13)	0.27764 (15)	0.0304 (5)
H5A	0.9412	0.0816	0.2111	0.037*
C6A	0.9442 (2)	0.05460 (13)	0.36475 (15)	0.0279 (5)
O61A	1.02988 (16)	0.00038 (9)	0.36625 (10)	0.0346 (4)
N1B	0.44262 (19)	0.40463 (11)	0.29932 (13)	0.0305 (4)
H1B	0.439 (2)	0.4352 (12)	0.2461 (15)	0.037*
C2B	0.5267 (2)	0.34287 (13)	0.30168 (14)	0.0268 (5)
N21B	0.6030 (2)	0.32707 (12)	0.21814 (13)	0.0369 (5)
H21B	0.592 (3)	0.3475 (14)	0.1561 (14)	0.044*
H22B	0.654 (2)	0.2850 (12)	0.2212 (19)	0.044*
N3B	0.53619 (18)	0.29800 (10)	0.38623 (11)	0.0274 (4)
C4B	0.4530 (2)	0.31394 (13)	0.46825 (14)	0.0274 (5)
N41B	0.4619 (2)	0.27026 (12)	0.55232 (13)	0.0347 (5)
H41B	0.528 (2)	0.2362 (13)	0.5550 (19)	0.042*
H42B	0.407 (2)	0.2794 (14)	0.6047 (15)	0.042*
C5B	0.3581 (2)	0.37523 (13)	0.46640 (16)	0.0348 (5)
H5B	0.2969	0.3843	0.5236	0.042*
C6B	0.3574 (2)	0.42020 (14)	0.38122 (16)	0.0343 (5)
H6B	0.2970	0.4630	0.3784	0.041*
C1X	0.8443 (3)	0.43271 (16)	0.0345 (2)	0.0518 (7)
H1X1	0.7975	0.4379	0.1025	0.078*
H1X2	0.8538	0.4839	0.0020	0.078*
H1X3	0.9341	0.4102	0.0436	0.078*
C2X	0.7636 (3)	0.38063 (16)	−0.03418 (19)	0.0441 (6)
O21X	0.66069 (18)	0.34777 (12)	0.00005 (12)	0.0524 (5)
N3X	0.8089 (2)	0.37062 (14)	−0.13257 (16)	0.0507 (6)
C31X	0.7378 (3)	0.3197 (2)	−0.2014 (2)	0.0666 (9)
H31A	0.6505	0.3051	−0.1688	0.100*
H31B	0.7920	0.2730	−0.2150	0.100*
H31C	0.7225	0.3465	−0.2672	0.100*
C32X	0.9255 (3)	0.4111 (2)	−0.1775 (2)	0.0743 (10)
H32A	0.9644	0.4447	−0.1247	0.111*
H32B	0.8974	0.4426	−0.2363	0.111*
H32C	0.9934	0.3732	−0.2016	0.111*
C1Y	0.0189 (3)	0.68053 (19)	0.4631 (2)	0.0680 (9)
H1YA	0.0568	0.7267	0.4958	0.102*	0.584 (7)
H1YB	−0.0766	0.6751	0.4848	0.102*	0.584 (7)
H1YC	0.0264	0.6859	0.3872	0.102*	0.584 (7)
H1YD	−0.0373	0.7254	0.4827	0.102*	0.416 (7)
H1YE	0.1020	0.6984	0.4269	0.102*	0.416 (7)
H1YF	−0.0312	0.6466	0.4169	0.102*	0.416 (7)
O21Y	0.1604 (3)	0.56219 (17)	0.43991 (17)	0.1078 (11)
C31Y	0.1779 (5)	0.5293 (2)	0.6325 (2)	0.0852 (12)
H3YA	0.2131	0.5389	0.7017	0.128*	0.584 (7)
H3YB	0.2534	0.5190	0.5831	0.128*	0.584 (7)
H3YC	0.1174	0.4842	0.6354	0.128*	0.584 (7)
H3YD	0.1390	0.5528	0.6961	0.128*	0.416 (7)
H3YE	0.1476	0.4753	0.6276	0.128*	0.416 (7)
H3YF	0.2769	0.5307	0.6344	0.128*	0.416 (7)
C32Y	0.0213 (4)	0.6485 (2)	0.6695 (2)	0.0854 (11)
H4YA	−0.0320	0.6169	0.7191	0.128*	0.584 (7)
H4YB	−0.0396	0.6800	0.6282	0.128*	0.584 (7)
H4YC	0.0817	0.6827	0.7076	0.128*	0.584 (7)
H4YD	−0.0350	0.6950	0.6790	0.128*	0.416 (7)
H4YE	−0.0279	0.6032	0.6967	0.128*	0.416 (7)
H4YF	0.1053	0.6550	0.7071	0.128*	0.416 (7)
C2Y	0.0980 (6)	0.6078 (3)	0.4969 (4)	0.0554 (15)	0.584 (7)
N3Y	0.1039 (4)	0.5967 (2)	0.5988 (3)	0.0509 (13)	0.584 (7)
C2Y'	0.1306 (10)	0.5754 (5)	0.5361 (5)	0.075 (3)	0.416 (7)
N3Y'	0.0540 (6)	0.6373 (3)	0.5573 (4)	0.0506 (18)	0.416 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1A	0.0320 (10)	0.0302 (11)	0.0184 (8)	0.0025 (8)	0.0013 (7)	−0.0010 (7)
C2A	0.0285 (11)	0.0310 (13)	0.0192 (9)	−0.0024 (9)	0.0035 (8)	−0.0020 (8)
S21A	0.0414 (3)	0.0478 (4)	0.0179 (2)	0.0139 (3)	0.0071 (2)	0.0008 (2)
N3A	0.0299 (10)	0.0341 (12)	0.0197 (8)	0.0070 (8)	0.0067 (7)	0.0012 (7)
C4A	0.0314 (12)	0.0352 (13)	0.0207 (9)	−0.0024 (10)	0.0049 (8)	−0.0006 (9)
O41A	0.0440 (10)	0.0493 (11)	0.0209 (7)	0.0139 (8)	0.0099 (6)	0.0074 (7)
C5A	0.0351 (12)	0.0377 (14)	0.0181 (9)	0.0033 (10)	0.0063 (8)	−0.0045 (9)
C6A	0.0315 (12)	0.0291 (13)	0.0228 (9)	−0.0018 (10)	0.0006 (8)	−0.0061 (8)
O61A	0.0461 (10)	0.0356 (9)	0.0218 (7)	0.0131 (8)	0.0024 (6)	−0.0050 (6)
N1B	0.0395 (11)	0.0301 (11)	0.0218 (8)	0.0011 (8)	0.0028 (7)	0.0069 (7)
C2B	0.0311 (11)	0.0272 (12)	0.0220 (9)	−0.0045 (10)	0.0022 (8)	0.0023 (8)
N21B	0.0469 (12)	0.0412 (13)	0.0218 (8)	0.0099 (9)	0.0104 (8)	0.0093 (8)
N3B	0.0316 (10)	0.0313 (11)	0.0188 (8)	−0.0002 (8)	0.0052 (7)	0.0016 (7)
C4B	0.0303 (12)	0.0306 (12)	0.0210 (9)	−0.0030 (9)	0.0038 (8)	0.0004 (8)
N41B	0.0420 (12)	0.0387 (12)	0.0225 (8)	0.0094 (9)	0.0121 (8)	0.0068 (8)
C5B	0.0378 (13)	0.0399 (14)	0.0263 (10)	0.0065 (10)	0.0085 (9)	0.0009 (9)
C6B	0.0361 (13)	0.0363 (14)	0.0303 (11)	0.0056 (10)	0.0035 (9)	0.0015 (9)
C1X	0.0526 (17)	0.0500 (18)	0.0520 (15)	0.0091 (13)	0.0109 (12)	0.0029 (13)
C2X	0.0447 (15)	0.0496 (17)	0.0374 (12)	0.0151 (13)	0.0074 (11)	0.0160 (11)
O21X	0.0443 (11)	0.0753 (14)	0.0368 (9)	−0.0009 (10)	0.0107 (7)	0.0167 (9)
N3X	0.0467 (13)	0.0657 (17)	0.0387 (11)	0.0089 (11)	0.0132 (9)	0.0112 (10)
C31X	0.0523 (18)	0.105 (3)	0.0426 (14)	0.0062 (17)	0.0019 (13)	−0.0005 (16)
C32X	0.059 (2)	0.100 (3)	0.0617 (18)	0.0045 (18)	0.0297 (15)	0.0226 (18)
C1Y	0.070 (2)	0.064 (2)	0.0691 (19)	0.0144 (16)	0.0058 (16)	0.0181 (16)
O21Y	0.158 (3)	0.115 (2)	0.0500 (12)	0.085 (2)	0.0147 (14)	−0.0126 (13)
C31Y	0.136 (4)	0.062 (2)	0.0581 (18)	0.038 (2)	−0.014 (2)	−0.0018 (16)
C32Y	0.090 (3)	0.103 (3)	0.0623 (19)	0.001 (2)	0.0225 (17)	−0.0313 (19)
C2Y	0.067 (4)	0.051 (4)	0.047 (3)	0.018 (3)	0.013 (3)	−0.003 (2)
N3Y	0.065 (3)	0.047 (3)	0.040 (2)	0.011 (2)	0.0033 (19)	−0.0061 (19)
C2Y'	0.107 (7)	0.065 (6)	0.054 (5)	0.045 (5)	−0.010 (5)	−0.012 (4)
N3Y'	0.059 (4)	0.046 (4)	0.046 (3)	0.014 (3)	0.012 (3)	−0.004 (3)

Geometric parameters (Å, º)

N1A—C2A	1.339 (3)	C31X—H31A	0.9800
N1A—C6A	1.390 (3)	C31X—H31B	0.9800
N1A—H1A	0.846 (15)	C31X—H31C	0.9800
C2A—N3A	1.350 (3)	C32X—H32A	0.9800
C2A—S21A	1.682 (2)	C32X—H32B	0.9800
N3A—C4A	1.400 (2)	C32X—H32C	0.9800
N3A—H3A	0.874 (16)	C1Y—N3Y'	1.474 (5)
C4A—O41A	1.258 (2)	C1Y—C2Y	1.547 (5)
C4A—C5A	1.389 (3)	C1Y—H1YA	0.9800
C5A—C6A	1.387 (3)	C1Y—H1YB	0.9800
C5A—H5A	0.9500	C1Y—H1YC	0.9800
C6A—O61A	1.262 (3)	C1Y—H1YD	0.9800
N1B—C2B	1.352 (3)	C1Y—H1YE	0.9800
N1B—C6B	1.354 (3)	C1Y—H1YF	0.9800
N1B—H1B	0.865 (16)	O21Y—C2Y	1.227 (5)
C2B—N21B	1.321 (3)	O21Y—C2Y'	1.283 (6)
C2B—N3B	1.340 (2)	C31Y—N3Y	1.448 (5)
N21B—H21B	0.881 (16)	C31Y—C2Y'	1.556 (6)
N21B—H22B	0.885 (17)	C31Y—H3YA	0.9800
N3B—C4B	1.345 (3)	C31Y—H3YB	0.9800
C4B—N41B	1.323 (3)	C31Y—H3YC	0.9800
C4B—C5B	1.414 (3)	C31Y—H3YD	0.9800
N41B—H41B	0.878 (16)	C31Y—H3YE	0.9800
N41B—H42B	0.866 (17)	C31Y—H3YF	0.9800
C5B—C6B	1.342 (3)	C32Y—N3Y'	1.480 (5)
C5B—H5B	0.9500	C32Y—N3Y	1.498 (5)
C6B—H6B	0.9500	C32Y—H4YA	0.9800
C1X—C2X	1.506 (4)	C32Y—H4YB	0.9800
C1X—H1X1	0.9800	C32Y—H4YC	0.9800
C1X—H1X2	0.9800	C32Y—H4YD	0.9800
C1X—H1X3	0.9800	C32Y—H4YE	0.9800
C2X—O21X	1.233 (3)	C32Y—H4YF	0.9800
C2X—N3X	1.340 (3)	C2Y—N3Y	1.327 (6)
N3X—C31X	1.446 (4)	C2Y'—N3Y'	1.332 (7)
N3X—C32X	1.450 (4)
C2A—N1A—C6A	125.17 (17)	H31A—C31X—H31C	109.5
C2A—N1A—H1A	119.7 (16)	H31B—C31X—H31C	109.5
C6A—N1A—H1A	115.1 (16)	N3X—C32X—H32A	109.5
N1A—C2A—N3A	115.85 (17)	N3X—C32X—H32B	109.5
N1A—C2A—S21A	121.13 (15)	H32A—C32X—H32B	109.5
N3A—C2A—S21A	123.01 (16)	N3X—C32X—H32C	109.5
C2A—N3A—C4A	124.60 (18)	H32A—C32X—H32C	109.5
C2A—N3A—H3A	118.5 (15)	H32B—C32X—H32C	109.5
C4A—N3A—H3A	116.8 (15)	C2Y—C1Y—H1YA	109.5
O41A—C4A—C5A	126.01 (18)	C2Y—C1Y—H1YB	109.5
O41A—C4A—N3A	117.38 (19)	H1YA—C1Y—H1YB	109.5
C5A—C4A—N3A	116.61 (17)	C2Y—C1Y—H1YC	109.5
C6A—C5A—C4A	120.92 (18)	H1YA—C1Y—H1YC	109.5
C6A—C5A—H5A	119.5	H1YB—C1Y—H1YC	109.5
C4A—C5A—H5A	119.5	N3Y'—C1Y—H1YD	109.5
O61A—C6A—C5A	126.44 (19)	N3Y'—C1Y—H1YE	109.5
O61A—C6A—N1A	116.72 (18)	H1YD—C1Y—H1YE	109.5
C5A—C6A—N1A	116.83 (19)	N3Y'—C1Y—H1YF	109.5
C2B—N1B—C6B	120.42 (18)	H1YD—C1Y—H1YF	109.5
C2B—N1B—H1B	122.4 (16)	H1YE—C1Y—H1YF	109.5
C6B—N1B—H1B	117.2 (16)	N3Y—C31Y—H3YA	109.5
N21B—C2B—N3B	119.2 (2)	N3Y—C31Y—H3YB	109.5
N21B—C2B—N1B	118.67 (18)	H3YA—C31Y—H3YB	109.5
N3B—C2B—N1B	122.14 (18)	N3Y—C31Y—H3YC	109.5
C2B—N21B—H21B	124.9 (17)	H3YA—C31Y—H3YC	109.5
C2B—N21B—H22B	116.4 (17)	H3YB—C31Y—H3YC	109.5
H21B—N21B—H22B	117 (2)	C2Y'—C31Y—H3YD	109.5
C2B—N3B—C4B	117.48 (18)	C2Y'—C31Y—H3YE	109.5
N41B—C4B—N3B	118.0 (2)	H3YD—C31Y—H3YE	109.5
N41B—C4B—C5B	120.04 (19)	C2Y'—C31Y—H3YF	109.5
N3B—C4B—C5B	121.93 (18)	H3YD—C31Y—H3YF	109.5
C4B—N41B—H41B	118.8 (17)	H3YE—C31Y—H3YF	109.5
C4B—N41B—H42B	118.4 (17)	N3Y—C32Y—H4YA	109.5
H41B—N41B—H42B	123 (2)	N3Y—C32Y—H4YB	109.5
C6B—C5B—C4B	117.8 (2)	H4YA—C32Y—H4YB	109.5
C6B—C5B—H5B	121.1	N3Y—C32Y—H4YC	109.5
C4B—C5B—H5B	121.1	H4YA—C32Y—H4YC	109.5
C5B—C6B—N1B	120.0 (2)	H4YB—C32Y—H4YC	109.5
C5B—C6B—H6B	120.0	N3Y'—C32Y—H4YD	109.5
N1B—C6B—H6B	120.0	N3Y'—C32Y—H4YE	109.5
C2X—C1X—H1X1	109.5	H4YD—C32Y—H4YE	109.5
C2X—C1X—H1X2	109.5	N3Y'—C32Y—H4YF	109.5
H1X1—C1X—H1X2	109.5	H4YD—C32Y—H4YF	109.5
C2X—C1X—H1X3	109.5	H4YE—C32Y—H4YF	109.5
H1X1—C1X—H1X3	109.5	O21Y—C2Y—N3Y	117.4 (4)
H1X2—C1X—H1X3	109.5	O21Y—C2Y—C1Y	126.9 (4)
O21X—C2X—N3X	121.7 (3)	N3Y—C2Y—C1Y	115.6 (4)
O21X—C2X—C1X	120.8 (2)	C2Y—N3Y—C31Y	116.7 (4)
N3X—C2X—C1X	117.6 (2)	C2Y—N3Y—C32Y	118.2 (4)
C2X—N3X—C31X	120.1 (2)	C31Y—N3Y—C32Y	124.6 (3)
C2X—N3X—C32X	123.4 (3)	O21Y—C2Y'—N3Y'	116.8 (5)
C31X—N3X—C32X	116.4 (2)	O21Y—C2Y'—C31Y	127.7 (5)
N3X—C31X—H31A	109.5	N3Y'—C2Y'—C31Y	115.4 (5)
N3X—C31X—H31B	109.5	C2Y'—N3Y'—C1Y	112.6 (5)
H31A—C31X—H31B	109.5	C2Y'—N3Y'—C32Y	114.2 (5)
N3X—C31X—H31C	109.5	C1Y—N3Y'—C32Y	133.3 (4)
C6A—N1A—C2A—N3A	−0.7 (3)	C2B—N3B—C4B—C5B	0.3 (3)
C6A—N1A—C2A—S21A	178.18 (16)	N41B—C4B—C5B—C6B	176.9 (2)
N1A—C2A—N3A—C4A	0.9 (3)	N3B—C4B—C5B—C6B	−3.1 (3)
S21A—C2A—N3A—C4A	−177.98 (16)	C4B—C5B—C6B—N1B	2.2 (3)
C2A—N3A—C4A—O41A	−179.6 (2)	C2B—N1B—C6B—C5B	1.5 (3)
C2A—N3A—C4A—C5A	0.1 (3)	O21X—C2X—N3X—C31X	−0.6 (4)
O41A—C4A—C5A—C6A	178.4 (2)	C1X—C2X—N3X—C31X	178.4 (2)
N3A—C4A—C5A—C6A	−1.4 (3)	O21X—C2X—N3X—C32X	176.8 (3)
C4A—C5A—C6A—O61A	−179.7 (2)	C1X—C2X—N3X—C32X	−4.2 (4)
C4A—C5A—C6A—N1A	1.5 (3)	O21Y—C2Y—N3Y—C31Y	−3.2 (8)
C2A—N1A—C6A—O61A	−179.40 (19)	C1Y—C2Y—N3Y—C31Y	−179.7 (4)
C2A—N1A—C6A—C5A	−0.5 (3)	O21Y—C2Y—N3Y—C32Y	−176.2 (5)
C6B—N1B—C2B—N21B	176.3 (2)	C1Y—C2Y—N3Y—C32Y	7.3 (7)
C6B—N1B—C2B—N3B	−4.5 (3)	O21Y—C2Y'—N3Y'—C1Y	−0.8 (11)
N21B—C2B—N3B—C4B	−177.37 (19)	C31Y—C2Y'—N3Y'—C1Y	176.9 (6)
N1B—C2B—N3B—C4B	3.5 (3)	O21Y—C2Y'—N3Y'—C32Y	179.0 (7)
C2B—N3B—C4B—N41B	−179.71 (19)	C31Y—C2Y'—N3Y'—C32Y	−3.2 (11)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1A—H1A···O61A^i	0.85 (2)	1.91 (2)	2.753 (2)	175 (2)
N3A—H3A···N3B	0.87 (2)	2.23 (2)	3.099 (3)	173 (2)
N1B—H1B···O61A^ii	0.87 (2)	1.85 (2)	2.700 (2)	168 (2)
N21B—H21B···O21X	0.88 (2)	2.10 (2)	2.866 (2)	145 (2)
N21B—H22B···O41A	0.89 (2)	1.91 (2)	2.795 (3)	174 (2)
N41B—H41B···S21A	0.88 (2)	2.47 (2)	3.336 (2)	171 (2)
N41B—H42B···O41A^iii	0.87 (2)	1.98 (2)	2.846 (2)	173 (2)
C6B—H6B···O21Y	0.95	2.30	3.203 (3)	158

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