Supra­molecular inter­actions in some organic hydrated 2,4,6-tri­amino­py­rimi­din­ium carboxyl­ate and sulfate salts

Four salts, namely, 2,4,6-tri­amino­py­rimi­din­ium 6-chloro­nicotinate dihydrate, C₄H₈N₅⁺·C₆H₃ClNO₂⁻·2H₂O, (I), 2,4,6-tri­amino­pyrimidine­diium pyridine-2,6-di­carboxyl­ate dihydrate, C₄H₉N₅²⁺·C₇H₃NO₄²⁻·2H₂O, (II), 2,4,6-tri­amino­pyrimidine­diium sulfate monohydrate, C₄H₉N₅²⁺·SO₄²⁻·H₂O, (III), and 2,4,6-tri­amino­py­rimi­din­ium 3,5-di­nitro­benzoate dihydrate, C₄H₈N₅⁺·C₇H₃N₂O₆⁻·2H₂O, (IV), were synthesized and characterized by X-ray diffraction techniques. Proton transfer from the corresponding acid to the pyrimidine base has occurred in all four crystal structures. Of the four salts, two [(I) and (IV)] exist as monoprotonated bases and two [(II) and (III)] exist as diprotonated bases. In all four crystal structures, the acid inter­acts with the pyrimidine base through N—H...O hydro­gen bonds, generating an R₂²(8) ring motif. The sulfate group mimics the role of the carboxyl­ate anions. The water mol­ecules present in com­pounds (I)–(IV) form water-mediated large ring motifs. The formation of water-mediated inter­actions in these crystal structures can be used as a model in the study of the hydration of nucleobases. Water mol­ecules play an important role in building supra­molecular structures. In addition to these strong hydro­gen-bonding inter­actions, some of the crystal structures are further enriched by aromatic π–π stacking inter­actions [(I) and (II)].

Computing details

Data collection: APEX3 (Bruker, 2016) for (I), (II); APEX2 (Bruker, 2010) for (III); CrysAlis PRO (Rigaku OD, 2022) for (IV). Cell refinement: SAINT (Bruker, 2016) for (I), (II); SAINT (Bruker, 2010) for (III); CrysAlis PRO (Rigaku OD, 2022) for (IV). Data reduction: SAINT (Bruker, 2016) for (I), (II); SAINT (Bruker, 2010) for (III); CrysAlis PRO (Rigaku OD, 2022) for (IV). Program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a) for (I), (II); SHELXT (Sheldrick, 2015a) for (III); SHELXT (Sheldrick, 2015a) for (IV). Program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b) for (I), (II); SHELXL2018 (Sheldrick, 2015b) for (III); SHELXL2018 (Sheldrick, 2015b) for (IV). For all structures, molecular graphics: PLATON (Spek, 2020), Mercury (Macrae et al., 2020) and POVRay (Cason, 2004); software used to prepare material for publication: PLATON (Spek, 2020) and publCIF (Westrip, 2010).

2,4,6-Triaminopyrimidinium 6-chloronicotinate dihydrate (I)

Crystal data

C4H8O2N5^+·C6H3ClO2N^−·2H2O	Z = 2
Mr = 318.73	F(000) = 332
Triclinic, P1	Dx = 1.580 Mg m^−3
a = 8.3769 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.7294 (4) Å	Cell parameters from 9926 reflections
c = 9.7804 (5) Å	θ = 2.5–27.5°
α = 74.8391 (17)°	µ = 0.31 mm^−1
β = 79.5481 (18)°	T = 100 K
γ = 78.3934 (16)°	Block, yellow
V = 669.88 (6) Å^3	0.17 × 0.11 × 0.06 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	2673 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.054
φ and ω scans	θmax = 27.6°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −10→10
Tmin = 0.964, Tmax = 1.000	k = −11→11
27526 measured reflections	l = −12→12
3082 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: mixed
wR(F^2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ^2(Fo^2) + (0.0353P)^2 + 0.2511P] where P = (Fo^2 + 2Fc^2)/3
3082 reflections	(Δ/σ)max < 0.001
227 parameters	Δρmax = 0.31 e Å^−3
0 restraints	Δρmin = −0.26 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
Cl1	0.48345 (4)	−0.31415 (3)	0.92646 (3)	0.01681 (10)
O1	0.42208 (11)	0.46362 (11)	0.67420 (10)	0.0172 (2)
O2	0.18441 (11)	0.47582 (10)	0.81893 (10)	0.0156 (2)
O3W	0.75791 (13)	0.45506 (12)	0.65303 (12)	0.0208 (2)
H3O1	0.659 (3)	0.454 (3)	0.654 (2)	0.049 (6)*
H3O2	0.774 (3)	0.449 (3)	0.739 (2)	0.049 (6)*
O4W	−0.12749 (13)	0.42132 (13)	0.91072 (12)	0.0232 (2)
H4O1	−0.024 (3)	0.427 (2)	0.889 (2)	0.038 (5)*
H4O2	−0.161 (2)	0.448 (2)	0.989 (2)	0.040 (6)*
N1	0.15807 (13)	0.80561 (13)	0.67444 (11)	0.0124 (2)
H1N	0.1790 (19)	0.699 (2)	0.7085 (16)	0.015*
N2	0.26057 (13)	1.04765 (12)	0.55819 (11)	0.0132 (2)
N3	0.42664 (14)	0.80035 (13)	0.57023 (12)	0.0154 (2)
H3N1	0.509 (2)	0.8465 (19)	0.5349 (18)	0.018*
H3N2	0.434 (2)	0.698 (2)	0.5994 (17)	0.018*
N4	−0.11176 (14)	0.79619 (14)	0.78005 (12)	0.0158 (2)
H4N1	−0.091 (2)	0.695 (2)	0.7891 (17)	0.019*
H4N2	−0.213 (2)	0.846 (2)	0.7870 (17)	0.019*
N5	0.08594 (15)	1.28834 (13)	0.55192 (13)	0.0164 (2)
H5N1	0.162 (2)	1.3353 (19)	0.4939 (18)	0.020*
H5N2	−0.014 (2)	1.3419 (19)	0.5698 (17)	0.020*
N6	0.54373 (13)	−0.02468 (13)	0.81255 (12)	0.0136 (2)
C1	0.28183 (15)	0.88810 (14)	0.59977 (13)	0.0120 (2)
C2	0.00364 (15)	0.88490 (15)	0.70866 (13)	0.0122 (2)
C3	−0.02338 (15)	1.05028 (15)	0.66965 (13)	0.0133 (2)
H3	−0.128013	1.110136	0.693875	0.016*
C4	0.10826 (15)	1.12815 (15)	0.59292 (13)	0.0122 (2)
C5	0.42576 (15)	−0.10627 (14)	0.88591 (13)	0.0122 (2)
C6	0.26660 (16)	−0.03915 (15)	0.92996 (14)	0.0142 (3)
H6	0.187685	−0.104315	0.983054	0.017*
C7	0.22708 (15)	0.12717 (15)	0.89341 (13)	0.0137 (3)
H7	0.119902	0.178871	0.922575	0.016*
C8	0.34647 (15)	0.21790 (14)	0.81326 (13)	0.0121 (2)
C9	0.50166 (15)	0.13559 (15)	0.77674 (13)	0.0132 (2)
H9	0.583448	0.196877	0.722825	0.016*
C10	0.31547 (15)	0.39896 (15)	0.76525 (13)	0.0125 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01833 (17)	0.00803 (15)	0.02242 (17)	−0.00142 (11)	−0.00323 (12)	−0.00092 (11)
O1	0.0139 (4)	0.0108 (4)	0.0229 (5)	−0.0023 (3)	0.0017 (4)	0.0002 (4)
O2	0.0125 (4)	0.0108 (4)	0.0212 (5)	0.0001 (3)	0.0006 (4)	−0.0035 (4)
O3W	0.0134 (5)	0.0206 (5)	0.0264 (6)	−0.0035 (4)	−0.0001 (4)	−0.0033 (4)
O4W	0.0145 (5)	0.0298 (6)	0.0260 (6)	−0.0029 (4)	0.0014 (4)	−0.0109 (5)
N1	0.0113 (5)	0.0086 (5)	0.0153 (5)	−0.0008 (4)	−0.0006 (4)	−0.0009 (4)
N2	0.0126 (5)	0.0109 (5)	0.0148 (5)	−0.0017 (4)	0.0001 (4)	−0.0021 (4)
N3	0.0121 (5)	0.0094 (5)	0.0211 (6)	−0.0012 (4)	0.0024 (4)	−0.0010 (4)
N4	0.0122 (5)	0.0107 (5)	0.0217 (6)	−0.0015 (4)	0.0010 (4)	−0.0014 (4)
N5	0.0146 (6)	0.0101 (5)	0.0213 (6)	−0.0015 (4)	0.0018 (5)	−0.0015 (4)
N6	0.0129 (5)	0.0115 (5)	0.0163 (5)	−0.0022 (4)	−0.0019 (4)	−0.0025 (4)
C1	0.0129 (6)	0.0116 (6)	0.0113 (6)	−0.0021 (5)	−0.0016 (5)	−0.0023 (4)
C2	0.0118 (6)	0.0135 (6)	0.0115 (6)	−0.0023 (5)	−0.0019 (4)	−0.0031 (5)
C3	0.0103 (6)	0.0125 (6)	0.0158 (6)	−0.0007 (5)	0.0000 (5)	−0.0034 (5)
C4	0.0131 (6)	0.0122 (6)	0.0117 (6)	−0.0011 (5)	−0.0022 (5)	−0.0037 (4)
C5	0.0152 (6)	0.0088 (5)	0.0130 (6)	−0.0014 (5)	−0.0045 (5)	−0.0015 (4)
C6	0.0134 (6)	0.0135 (6)	0.0153 (6)	−0.0048 (5)	−0.0007 (5)	−0.0015 (5)
C7	0.0120 (6)	0.0138 (6)	0.0147 (6)	−0.0007 (5)	−0.0013 (5)	−0.0038 (5)
C8	0.0133 (6)	0.0111 (6)	0.0121 (6)	−0.0022 (5)	−0.0029 (5)	−0.0022 (5)
C9	0.0127 (6)	0.0111 (6)	0.0156 (6)	−0.0034 (5)	−0.0015 (5)	−0.0021 (5)
C10	0.0119 (6)	0.0117 (6)	0.0145 (6)	−0.0024 (5)	−0.0037 (5)	−0.0026 (5)

Geometric parameters (Å, º)

Cl1—C5	1.7389 (12)	N4—H4N2	0.872 (18)
O1—C10	1.2492 (15)	N5—C4	1.3341 (16)
O2—C10	1.2688 (15)	N5—H5N1	0.866 (17)
O3W—H3O1	0.83 (2)	N5—H5N2	0.887 (17)
O3W—H3O2	0.86 (2)	N6—C5	1.3257 (16)
O4W—H4O1	0.86 (2)	N6—C9	1.3396 (16)
O4W—H4O2	0.84 (2)	C2—C3	1.3757 (17)
N1—C2	1.3669 (16)	C3—C4	1.4057 (17)
N1—C1	1.3702 (16)	C3—H3	0.9500
N1—H1N	0.896 (16)	C5—C6	1.3842 (18)
N2—C1	1.3293 (16)	C6—C7	1.3868 (17)
N2—C4	1.3579 (16)	C6—H6	0.9500
N3—C1	1.3253 (16)	C7—C8	1.3970 (17)
N3—H3N1	0.844 (17)	C7—H7	0.9500
N3—H3N2	0.859 (17)	C8—C9	1.3870 (17)
N4—C2	1.3398 (16)	C8—C10	1.5090 (16)
N4—H4N1	0.847 (17)	C9—H9	0.9500
H3O1—O3W—H3O2	108 (2)	C2—C3—H3	121.0
H4O1—O4W—H4O2	107.8 (18)	C4—C3—H3	121.0
C2—N1—C1	121.01 (11)	N5—C4—N2	117.32 (11)
C2—N1—H1N	118.4 (10)	N5—C4—C3	119.71 (12)
C1—N1—H1N	120.4 (10)	N2—C4—C3	122.97 (11)
C1—N2—C4	116.92 (11)	N6—C5—C6	125.40 (11)
C1—N3—H3N1	119.3 (11)	N6—C5—Cl1	114.84 (9)
C1—N3—H3N2	117.0 (11)	C6—C5—Cl1	119.76 (9)
H3N1—N3—H3N2	123.1 (15)	C5—C6—C7	117.25 (11)
C2—N4—H4N1	119.1 (11)	C5—C6—H6	121.4
C2—N4—H4N2	116.9 (11)	C7—C6—H6	121.4
H4N1—N4—H4N2	120.2 (15)	C6—C7—C8	119.33 (11)
C4—N5—H5N1	119.4 (11)	C6—C7—H7	120.3
C4—N5—H5N2	118.1 (10)	C8—C7—H7	120.3
H5N1—N5—H5N2	121.1 (15)	C9—C8—C7	117.59 (11)
C5—N6—C9	116.14 (11)	C9—C8—C10	118.79 (11)
N3—C1—N2	120.80 (11)	C7—C8—C10	123.63 (11)
N3—C1—N1	116.48 (11)	N6—C9—C8	124.26 (11)
N2—C1—N1	122.72 (11)	N6—C9—H9	117.9
N4—C2—N1	117.69 (11)	C8—C9—H9	117.9
N4—C2—C3	124.05 (12)	O1—C10—O2	124.15 (11)
N1—C2—C3	118.26 (11)	O1—C10—C8	117.19 (11)
C2—C3—C4	118.09 (11)	O2—C10—C8	118.66 (11)
C4—N2—C1—N3	179.98 (11)	C9—N6—C5—Cl1	178.42 (9)
C4—N2—C1—N1	−0.06 (18)	N6—C5—C6—C7	0.5 (2)
C2—N1—C1—N3	−179.19 (11)	Cl1—C5—C6—C7	−179.39 (9)
C2—N1—C1—N2	0.86 (19)	C5—C6—C7—C8	1.02 (18)
C1—N1—C2—N4	179.07 (11)	C6—C7—C8—C9	−1.44 (18)
C1—N1—C2—C3	−1.78 (18)	C6—C7—C8—C10	178.70 (11)
N4—C2—C3—C4	−179.01 (12)	C5—N6—C9—C8	0.97 (19)
N1—C2—C3—C4	1.90 (18)	C7—C8—C9—N6	0.44 (19)
C1—N2—C4—N5	179.83 (11)	C10—C8—C9—N6	−179.69 (11)
C1—N2—C4—C3	0.25 (18)	C9—C8—C10—O1	12.24 (17)
C2—C3—C4—N5	179.23 (12)	C7—C8—C10—O1	−167.90 (12)
C2—C3—C4—N2	−1.20 (19)	C9—C8—C10—O2	−167.76 (12)
C9—N6—C5—C6	−1.46 (19)	C7—C8—C10—O2	12.11 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3W—H3O1···O1	0.83 (2)	1.95 (2)	2.7704 (14)	173 (2)
O3W—H3O2···O4W^i	0.86 (2)	1.95 (2)	2.7813 (16)	164 (2)
O4W—H4O1···O2	0.86 (2)	1.85 (2)	2.6990 (14)	168.9 (19)
O4W—H4O2···O2^ii	0.84 (2)	2.12 (2)	2.9389 (15)	166.1 (19)
N1—H1N···O1	0.896 (16)	2.628 (16)	3.3389 (14)	136.9 (13)
N1—H1N···O2	0.896 (16)	1.960 (16)	2.8395 (14)	166.7 (14)
N3—H3N1···N2^iii	0.844 (17)	2.245 (17)	3.0881 (15)	176.0 (15)
N3—H3N2···O1	0.859 (17)	1.998 (18)	2.8536 (14)	173.4 (15)
N4—H4N1···O4W	0.847 (17)	2.429 (17)	3.2069 (15)	153.1 (15)
N4—H4N2···N6^iv	0.872 (18)	2.127 (18)	2.9977 (16)	176.2 (15)
N5—H5N1···O3W^iii	0.866 (17)	2.152 (17)	2.9369 (15)	150.5 (15)
N5—H5N2···O3W^iv	0.887 (17)	2.092 (18)	2.9672 (15)	169.0 (15)

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

2,4,6-Triaminopyrimidinediium pyridine-2,6-dicarboxylate dihydrate (II)

Crystal data

C4H9O2N5^2+·C7H3NO4^2^−·2H2O	F(000) = 688
Mr = 328.30	Dx = 1.597 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.2567 (10) Å	Cell parameters from 9940 reflections
b = 12.7736 (14) Å	θ = 2.2–26.8°
c = 13.2612 (17) Å	µ = 0.13 mm^−1
β = 102.433 (5)°	T = 100 K
V = 1365.8 (3) Å^3	Block, colourless
Z = 4	0.07 × 0.07 × 0.06 mm

Data collection

Bruker D8 Venture Photon 2 diffractometer	2381 reflections with I > 2σ(I)
Radiation source: Incoatec IµS	Rint = 0.062
φ and ω scans	θmax = 26.8°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −10→10
Tmin = 0.932, Tmax = 1.000	k = −16→16
32550 measured reflections	l = −16→16
2912 independent reflections

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: mixed
wR(F^2) = 0.091	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0413P)^2 + 0.6912P] where P = (Fo^2 + 2Fc^2)/3
2912 reflections	(Δ/σ)max = 0.001
256 parameters	Δρmax = 0.26 e Å^−3
0 restraints	Δρmin = −0.24 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
O1	0.17203 (12)	0.56813 (7)	0.35545 (8)	0.0170 (2)
O2	0.43203 (12)	0.62708 (8)	0.37736 (9)	0.0208 (2)
O3	0.38164 (12)	1.10186 (8)	0.35889 (8)	0.0201 (2)
O4	0.57564 (12)	0.97863 (8)	0.36960 (8)	0.0202 (2)
O5W	0.32069 (13)	1.23146 (9)	0.63150 (9)	0.0224 (3)
H5O1	0.355 (3)	1.163 (2)	0.6358 (18)	0.054 (7)*
H5O2	0.422 (3)	1.271 (2)	0.6288 (19)	0.067 (8)*
O6W	0.14890 (13)	1.20081 (8)	0.43482 (9)	0.0211 (2)
H6O1	0.201 (3)	1.212 (2)	0.507 (2)	0.067 (8)*
H6O2	0.215 (3)	1.1541 (18)	0.4105 (18)	0.052 (7)*
N1	0.58721 (14)	0.45136 (9)	0.38436 (9)	0.0137 (3)
H1N	0.529 (2)	0.5172 (17)	0.3813 (15)	0.038 (5)*
N2	0.56826 (14)	0.26944 (9)	0.38233 (9)	0.0140 (3)
H2N	0.503 (3)	0.2074 (17)	0.3719 (15)	0.040 (6)*
N3	0.33458 (15)	0.37225 (10)	0.37324 (10)	0.0168 (3)
H3N1	0.273 (2)	0.3147 (16)	0.3785 (14)	0.030 (5)*
H3N2	0.287 (2)	0.4338 (17)	0.3713 (15)	0.037 (5)*
N4	0.83411 (16)	0.53921 (10)	0.39853 (10)	0.0166 (3)
H4N1	0.776 (2)	0.5981 (15)	0.3849 (13)	0.024 (5)*
H4N2	0.939 (2)	0.5409 (14)	0.3904 (14)	0.029 (5)*
N5	0.79749 (16)	0.16426 (9)	0.39607 (10)	0.0157 (3)
H5N1	0.731 (2)	0.1059 (15)	0.3888 (14)	0.029 (5)*
H5N2	0.908 (3)	0.1587 (15)	0.4067 (14)	0.031 (5)*
N6	0.33705 (14)	0.82574 (9)	0.36250 (9)	0.0138 (2)
C1	0.49534 (17)	0.36380 (11)	0.38010 (10)	0.0136 (3)
C2	0.75600 (17)	0.44703 (11)	0.39446 (10)	0.0134 (3)
C3	0.83366 (17)	0.35089 (11)	0.40126 (10)	0.0143 (3)
H3	0.950836	0.346337	0.410883	0.017*
C4	0.73710 (17)	0.26049 (11)	0.39376 (10)	0.0135 (3)
C5	0.21777 (17)	0.75282 (11)	0.35249 (10)	0.0132 (3)
C6	0.04991 (17)	0.77721 (11)	0.33394 (11)	0.0155 (3)
H6	−0.031299	0.723457	0.326612	0.019*
C7	0.00366 (17)	0.88163 (11)	0.32638 (11)	0.0163 (3)
H7	−0.109955	0.900887	0.315133	0.020*
C8	0.12559 (17)	0.95736 (11)	0.33549 (11)	0.0157 (3)
H8	0.096951	1.029456	0.329271	0.019*
C9	0.29155 (16)	0.92621 (11)	0.35397 (10)	0.0134 (3)
C10	0.27661 (17)	0.64008 (11)	0.36202 (10)	0.0139 (3)
C11	0.42960 (17)	1.00721 (11)	0.36221 (11)	0.0154 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0144 (5)	0.0121 (5)	0.0253 (5)	−0.0014 (4)	0.0061 (4)	−0.0008 (4)
O2	0.0128 (5)	0.0125 (5)	0.0364 (6)	0.0007 (4)	0.0036 (4)	−0.0007 (4)
O3	0.0150 (5)	0.0107 (5)	0.0357 (6)	−0.0012 (4)	0.0077 (4)	−0.0010 (4)
O4	0.0120 (5)	0.0153 (5)	0.0333 (6)	−0.0006 (4)	0.0045 (4)	0.0010 (4)
O5W	0.0130 (5)	0.0183 (6)	0.0365 (6)	0.0001 (4)	0.0067 (5)	−0.0003 (5)
O6W	0.0150 (5)	0.0164 (5)	0.0322 (6)	0.0010 (4)	0.0055 (5)	−0.0027 (5)
N1	0.0119 (6)	0.0098 (6)	0.0194 (6)	0.0012 (4)	0.0037 (5)	−0.0002 (4)
N2	0.0108 (6)	0.0113 (6)	0.0201 (6)	−0.0009 (4)	0.0038 (5)	−0.0012 (5)
N3	0.0125 (6)	0.0108 (6)	0.0271 (7)	−0.0007 (5)	0.0042 (5)	−0.0001 (5)
N4	0.0125 (6)	0.0117 (6)	0.0264 (7)	−0.0010 (5)	0.0061 (5)	0.0001 (5)
N5	0.0123 (6)	0.0125 (6)	0.0224 (6)	0.0002 (5)	0.0040 (5)	−0.0012 (5)
N6	0.0141 (6)	0.0128 (6)	0.0149 (6)	−0.0014 (4)	0.0038 (5)	−0.0001 (4)
C1	0.0131 (6)	0.0132 (7)	0.0142 (7)	0.0000 (5)	0.0027 (5)	0.0010 (5)
C2	0.0124 (6)	0.0154 (7)	0.0125 (6)	−0.0019 (5)	0.0030 (5)	−0.0015 (5)
C3	0.0112 (6)	0.0142 (7)	0.0173 (7)	−0.0003 (5)	0.0026 (5)	0.0003 (5)
C4	0.0129 (6)	0.0151 (7)	0.0125 (6)	0.0012 (5)	0.0031 (5)	−0.0002 (5)
C5	0.0146 (7)	0.0125 (6)	0.0132 (7)	−0.0008 (5)	0.0043 (5)	−0.0005 (5)
C6	0.0138 (7)	0.0139 (7)	0.0190 (7)	−0.0022 (5)	0.0042 (5)	0.0005 (5)
C7	0.0111 (6)	0.0178 (7)	0.0201 (7)	0.0006 (5)	0.0032 (5)	−0.0001 (6)
C8	0.0150 (7)	0.0133 (7)	0.0187 (7)	0.0016 (5)	0.0034 (5)	0.0002 (5)
C9	0.0140 (7)	0.0124 (7)	0.0144 (7)	−0.0010 (5)	0.0042 (5)	−0.0002 (5)
C10	0.0136 (6)	0.0140 (7)	0.0144 (7)	−0.0008 (5)	0.0033 (5)	−0.0013 (5)
C11	0.0152 (7)	0.0143 (7)	0.0164 (7)	−0.0008 (5)	0.0030 (5)	−0.0002 (5)

Geometric parameters (Å, º)

O1—C10	1.2512 (17)	N4—H4N2	0.90 (2)
O2—C10	1.2662 (17)	N5—C4	1.3243 (18)
O3—C11	1.2700 (17)	N5—H5N1	0.92 (2)
O4—C11	1.2434 (17)	N5—H5N2	0.89 (2)
O5W—H5O1	0.92 (3)	N6—C9	1.3351 (18)
O5W—H5O2	0.98 (3)	N6—C5	1.3413 (18)
O6W—H6O1	0.97 (3)	C2—C3	1.3793 (19)
O6W—H6O2	0.91 (3)	C3—C4	1.3946 (19)
N1—C1	1.3458 (17)	C3—H3	0.9500
N1—C2	1.3722 (17)	C5—C6	1.3898 (19)
N1—H1N	0.97 (2)	C5—C10	1.5164 (19)
N2—C1	1.3448 (18)	C6—C7	1.3850 (19)
N2—C4	1.3742 (18)	C6—H6	0.9500
N2—H2N	0.95 (2)	C7—C8	1.383 (2)
N3—C1	1.3152 (18)	C7—H7	0.9500
N3—H3N1	0.90 (2)	C8—C9	1.3969 (19)
N3—H3N2	0.87 (2)	C8—H8	0.9500
N4—C2	1.3381 (18)	C9—C11	1.5258 (19)
N4—H4N1	0.890 (19)
H5O1—O5W—H5O2	104 (2)	C4—C3—H3	120.6
H6O1—O6W—H6O2	106 (2)	N5—C4—N2	116.60 (12)
C1—N1—C2	121.47 (12)	N5—C4—C3	124.07 (13)
C1—N1—H1N	116.6 (12)	N2—C4—C3	119.32 (12)
C2—N1—H1N	121.9 (12)	N6—C5—C6	123.01 (13)
C1—N2—C4	121.05 (12)	N6—C5—C10	115.85 (12)
C1—N2—H2N	120.3 (12)	C6—C5—C10	121.13 (12)
C4—N2—H2N	118.6 (12)	C7—C6—C5	118.53 (13)
C1—N3—H3N1	120.1 (12)	C7—C6—H6	120.7
C1—N3—H3N2	120.8 (13)	C5—C6—H6	120.7
H3N1—N3—H3N2	118.7 (18)	C8—C7—C6	118.89 (13)
C2—N4—H4N1	120.0 (12)	C8—C7—H7	120.6
C2—N4—H4N2	119.1 (12)	C6—C7—H7	120.6
H4N1—N4—H4N2	116.7 (16)	C7—C8—C9	118.97 (13)
C4—N5—H5N1	122.3 (12)	C7—C8—H8	120.5
C4—N5—H5N2	116.3 (12)	C9—C8—H8	120.5
H5N1—N5—H5N2	121.3 (17)	N6—C9—C8	122.42 (12)
C9—N6—C5	118.16 (12)	N6—C9—C11	116.97 (12)
N3—C1—N2	121.03 (12)	C8—C9—C11	120.59 (12)
N3—C1—N1	119.08 (12)	O1—C10—O2	125.11 (13)
N2—C1—N1	119.89 (12)	O1—C10—C5	119.20 (12)
N4—C2—N1	116.04 (12)	O2—C10—C5	115.68 (12)
N4—C2—C3	124.58 (13)	O4—C11—O3	124.90 (13)
N1—C2—C3	119.37 (12)	O4—C11—C9	120.22 (12)
C2—C3—C4	118.81 (12)	O3—C11—C9	114.87 (12)
C2—C3—H3	120.6
C4—N2—C1—N3	−177.30 (13)	C10—C5—C6—C7	179.76 (13)
C4—N2—C1—N1	3.1 (2)	C5—C6—C7—C8	1.3 (2)
C2—N1—C1—N3	178.15 (13)	C6—C7—C8—C9	−1.2 (2)
C2—N1—C1—N2	−2.2 (2)	C5—N6—C9—C8	0.2 (2)
C1—N1—C2—N4	−179.57 (13)	C5—N6—C9—C11	−178.07 (12)
C1—N1—C2—C3	−0.5 (2)	C7—C8—C9—N6	0.5 (2)
N4—C2—C3—C4	−178.69 (13)	C7—C8—C9—C11	178.69 (13)
N1—C2—C3—C4	2.4 (2)	N6—C5—C10—O1	178.64 (12)
C1—N2—C4—N5	179.36 (12)	C6—C5—C10—O1	−1.7 (2)
C1—N2—C4—C3	−1.2 (2)	N6—C5—C10—O2	−0.69 (18)
C2—C3—C4—N5	177.88 (13)	C6—C5—C10—O2	178.96 (13)
C2—C3—C4—N2	−1.5 (2)	N6—C9—C11—O4	4.62 (19)
C9—N6—C5—C6	−0.1 (2)	C8—C9—C11—O4	−173.68 (13)
C9—N6—C5—C10	179.51 (12)	N6—C9—C11—O3	−176.61 (12)
N6—C5—C6—C7	−0.6 (2)	C8—C9—C11—O3	5.08 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5W—H5O1···O4^i	0.92 (3)	1.90 (3)	2.8178 (15)	174 (2)
O5W—H5O2···O2^i	0.98 (3)	1.79 (3)	2.7479 (15)	164 (2)
O5W—H5O2···N6^i	0.98 (3)	2.33 (3)	2.9033 (16)	116.8 (18)
O6W—H6O1···O5W	0.97 (3)	1.75 (3)	2.7157 (17)	173 (2)
O6W—H6O2···O3	0.91 (3)	1.79 (3)	2.6715 (15)	161 (2)
N1—H1N···O2	0.97 (2)	1.61 (2)	2.5762 (15)	179 (2)
N2—H2N···O3^ii	0.95 (2)	1.66 (2)	2.6167 (15)	176.5 (19)
N3—H3N1···O6W^ii	0.90 (2)	2.01 (2)	2.8899 (17)	162.6 (17)
N3—H3N2···O1	0.87 (2)	1.95 (2)	2.8251 (16)	175.3 (19)
N4—H4N1···O5W^i	0.890 (19)	2.312 (19)	3.1865 (17)	167.1 (16)
N4—H4N2···O1^iii	0.90 (2)	2.10 (2)	2.9889 (16)	170.0 (17)
N5—H5N1···O4^ii	0.92 (2)	2.05 (2)	2.9705 (16)	178.2 (17)
N5—H5N2···O6W^iv	0.89 (2)	2.02 (2)	2.8738 (17)	159.9 (17)

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

2,4,6-Triaminopyrimidinediium sulfate monohydrate (III)

Crystal data

C4H9N5^2+·SO4^2^−·H2O	F(000) = 504
Mr = 241.24	Dx = 1.809 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0198 (5) Å	Cell parameters from 6591 reflections
b = 10.1953 (5) Å	θ = 2.9–36.2°
c = 9.8987 (5) Å	µ = 0.38 mm^−1
β = 103.305 (2)°	T = 102 K
V = 885.85 (8) Å^3	Prism, pale yellow
Z = 4	0.28 × 0.19 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	2995 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.088
Absorption correction: multi-scan (SADABS; Bruker, 2010)	θmax = 36.3°, θmin = 2.8°
Tmin = 0.557, Tmax = 0.747	h = −15→12
24913 measured reflections	k = −16→16
4273 independent reflections	l = −15→16

Refinement

Refinement on F^2	Primary atom site location: dual
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.046	Hydrogen site location: mixed
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0495P)^2 + 0.2066P] where P = (Fo^2 + 2Fc^2)/3
4273 reflections	(Δ/σ)max = 0.001
176 parameters	Δρmax = 0.53 e Å^−3
3 restraints	Δρmin = −0.63 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
S1	0.75249 (4)	0.62812 (3)	0.55175 (3)	0.01149 (8)
O11	0.72337 (12)	0.77012 (9)	0.56144 (10)	0.0158 (2)
O12	0.91193 (12)	0.60853 (10)	0.54002 (10)	0.0169 (2)
O13	0.72829 (12)	0.56133 (10)	0.67637 (10)	0.0168 (2)
O14	0.64787 (12)	0.57325 (10)	0.42666 (10)	0.0190 (2)
O1W	0.51285 (13)	0.61216 (11)	0.15645 (11)	0.0195 (2)
H1W1	0.4223 (17)	0.639 (2)	0.145 (2)	0.031 (6)*
H1W2	0.549 (2)	0.623 (2)	0.2385 (17)	0.036 (6)*
N1	0.61140 (13)	0.30832 (11)	0.38069 (11)	0.0122 (2)
H1N	0.617 (3)	0.392 (2)	0.399 (3)	0.041 (6)*
N2	0.56919 (13)	0.12889 (11)	0.23213 (11)	0.0130 (2)
H2N	0.555 (2)	0.1051 (19)	0.148 (2)	0.029 (5)*
N3	0.52860 (14)	0.33810 (12)	0.14335 (12)	0.0147 (2)
H3N1	0.526 (2)	0.425 (2)	0.156 (2)	0.034 (6)*
H3N2	0.508 (2)	0.3074 (18)	0.060 (2)	0.018 (4)*
N4	0.60917 (14)	−0.08368 (11)	0.31013 (13)	0.0155 (2)
H4N1	0.567 (2)	−0.1033 (19)	0.227 (2)	0.025 (5)*
H4N2	0.632 (2)	−0.1377 (18)	0.380 (2)	0.015 (4)*
N5	0.69397 (14)	0.28398 (12)	0.61787 (12)	0.0144 (2)
H5N1	0.720 (2)	0.226 (2)	0.686 (2)	0.028 (5)*
H5N2	0.697 (2)	0.372 (2)	0.627 (2)	0.026 (5)*
C1	0.56896 (14)	0.26036 (12)	0.25055 (13)	0.0114 (2)
C2	0.61136 (14)	0.04289 (13)	0.34162 (13)	0.0116 (2)
C3	0.65431 (15)	0.09243 (12)	0.47556 (13)	0.0119 (2)
H3A	0.683450	0.035124	0.552793	0.014*
C4	0.65385 (14)	0.22699 (12)	0.49443 (13)	0.0111 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01454 (15)	0.01109 (14)	0.00814 (13)	0.00082 (11)	0.00118 (10)	−0.00046 (10)
O11	0.0200 (5)	0.0109 (4)	0.0160 (5)	0.0019 (4)	0.0031 (4)	−0.0006 (3)
O12	0.0175 (5)	0.0220 (5)	0.0113 (4)	0.0048 (4)	0.0035 (4)	0.0011 (3)
O13	0.0226 (5)	0.0172 (5)	0.0110 (4)	−0.0018 (4)	0.0049 (4)	0.0016 (3)
O14	0.0237 (5)	0.0169 (5)	0.0121 (4)	−0.0009 (4)	−0.0047 (4)	−0.0014 (3)
O1W	0.0234 (5)	0.0228 (5)	0.0115 (4)	0.0060 (4)	0.0028 (4)	0.0016 (4)
N1	0.0161 (5)	0.0115 (5)	0.0090 (4)	0.0010 (4)	0.0029 (4)	0.0002 (4)
N2	0.0168 (5)	0.0127 (5)	0.0088 (4)	0.0013 (4)	0.0018 (4)	−0.0010 (4)
N3	0.0187 (5)	0.0151 (5)	0.0099 (5)	0.0014 (4)	0.0022 (4)	0.0022 (4)
N4	0.0189 (6)	0.0121 (5)	0.0132 (5)	0.0012 (4)	−0.0009 (4)	−0.0018 (4)
N5	0.0200 (6)	0.0141 (5)	0.0084 (5)	0.0008 (4)	0.0022 (4)	−0.0008 (4)
C1	0.0109 (5)	0.0133 (5)	0.0100 (5)	0.0001 (4)	0.0026 (4)	−0.0002 (4)
C2	0.0108 (5)	0.0130 (5)	0.0107 (5)	0.0009 (4)	0.0018 (4)	0.0005 (4)
C3	0.0137 (6)	0.0123 (5)	0.0094 (5)	0.0004 (4)	0.0020 (4)	0.0009 (4)
C4	0.0112 (5)	0.0134 (5)	0.0088 (5)	0.0003 (4)	0.0025 (4)	0.0003 (4)

Geometric parameters (Å, º)

S1—O13	1.4686 (10)	N3—C1	1.3073 (17)
S1—O11	1.4784 (10)	N3—H3N1	0.90 (2)
S1—O12	1.4828 (11)	N3—H3N2	0.862 (19)
S1—O14	1.4828 (10)	N4—C2	1.3266 (17)
O1W—H1W1	0.845 (14)	N4—H4N1	0.85 (2)
O1W—H1W2	0.811 (15)	N4—H4N2	0.871 (19)
N1—C1	1.3484 (16)	N5—C4	1.3259 (16)
N1—C4	1.3797 (16)	N5—H5N1	0.89 (2)
N1—H1N	0.87 (2)	N5—H5N2	0.90 (2)
N2—C1	1.3527 (16)	C2—C3	1.3880 (17)
N2—C2	1.3778 (17)	C3—C4	1.3847 (17)
N2—H2N	0.85 (2)	C3—H3A	0.9500
O13—S1—O11	109.67 (6)	C2—N4—H4N2	116.1 (12)
O13—S1—O12	109.73 (6)	H4N1—N4—H4N2	126.4 (18)
O11—S1—O12	109.08 (6)	C4—N5—H5N1	112.0 (13)
O13—S1—O14	109.72 (6)	C4—N5—H5N2	121.6 (14)
O11—S1—O14	109.58 (6)	H5N1—N5—H5N2	126.3 (19)
O12—S1—O14	109.03 (6)	N3—C1—N1	121.36 (12)
H1W1—O1W—H1W2	104.0 (17)	N3—C1—N2	120.01 (12)
C1—N1—C4	121.74 (11)	N1—C1—N2	118.63 (11)
C1—N1—H1N	123.1 (16)	N4—C2—N2	116.60 (12)
C4—N1—H1N	115.1 (16)	N4—C2—C3	124.35 (12)
C1—N2—C2	122.23 (11)	N2—C2—C3	119.05 (11)
C1—N2—H2N	114.2 (14)	C4—C3—C2	118.73 (11)
C2—N2—H2N	122.9 (14)	C4—C3—H3A	120.6
C1—N3—H3N1	119.6 (14)	C2—C3—H3A	120.6
C1—N3—H3N2	121.0 (12)	N5—C4—N1	117.02 (11)
H3N1—N3—H3N2	119.4 (19)	N5—C4—C3	123.36 (12)
C2—N4—H4N1	115.9 (13)	N1—C4—C3	119.62 (11)
C4—N1—C1—N3	179.86 (12)	N4—C2—C3—C4	179.04 (13)
C4—N1—C1—N2	−0.36 (18)	N2—C2—C3—C4	−0.26 (19)
C2—N2—C1—N3	179.72 (12)	C1—N1—C4—N5	179.84 (12)
C2—N2—C1—N1	−0.06 (19)	C1—N1—C4—C3	0.46 (19)
C1—N2—C2—N4	−178.99 (12)	C2—C3—C4—N5	−179.48 (12)
C1—N2—C2—C3	0.37 (19)	C2—C3—C4—N1	−0.13 (19)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···S1^i	0.85 (1)	2.86 (2)	3.5328 (11)	138 (2)
O1W—H1W1···O11^i	0.85 (1)	2.02 (2)	2.8306 (15)	161 (2)
O1W—H1W2···O14	0.81 (2)	1.94 (2)	2.7010 (15)	157 (2)
N1—H1N···S1	0.87 (2)	2.95 (2)	3.7583 (12)	154 (2)
N1—H1N···O14	0.87 (2)	1.88 (2)	2.7462 (15)	173 (2)
N2—H2N···S1^ii	0.85 (2)	2.92 (2)	3.5445 (12)	131.5 (17)
N2—H2N···O12^ii	0.85 (2)	1.95 (2)	2.7460 (15)	155.6 (19)
N2—H2N···O12^iii	0.85 (2)	2.63 (2)	3.2010 (15)	125.6 (17)
N3—H3N1···O1W	0.90 (2)	1.91 (2)	2.8022 (16)	172 (2)
N3—H3N2···O12^ii	0.862 (19)	2.437 (19)	3.0836 (16)	132.3 (16)
N3—H3N2···O1W^iv	0.862 (19)	2.261 (19)	2.9484 (16)	136.7 (16)
N4—H4N1···S1^iii	0.85 (2)	2.98 (2)	3.6482 (13)	137.9 (17)
N4—H4N1···O12^iii	0.85 (2)	2.05 (2)	2.8616 (16)	160.9 (19)
N4—H4N2···S1^v	0.871 (19)	2.987 (19)	3.8212 (13)	161.2 (15)
N4—H4N2···O11^v	0.871 (19)	2.026 (19)	2.8795 (16)	166.3 (17)
N5—H5N1···S1^vi	0.89 (2)	2.74 (2)	3.5674 (12)	155.8 (17)
N5—H5N1···O11^vi	0.89 (2)	2.47 (2)	3.0925 (15)	126.9 (16)
N5—H5N1···O13^vi	0.89 (2)	2.14 (2)	3.0225 (16)	170.4 (18)
N5—H5N2···S1	0.90 (2)	2.79 (2)	3.6299 (13)	155.3 (18)
N5—H5N2···O13	0.90 (2)	2.00 (2)	2.8886 (16)	170.7 (19)
C3—H3A···O13^vi	0.95	2.63	3.3785 (16)	136

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

2,4,6-Triaminopyrimidinium 3,5-dinitrobenzoate dihydrate (IV)

Crystal data

C4H8N5^+·C7H3N2O6^−·2H2O	Z = 2
Mr = 373.30	F(000) = 388
Triclinic, P1	Dx = 1.528 Mg m^−3
a = 6.9770 (2) Å	Cu Kα radiation, λ = 1.54184 Å
b = 10.5805 (3) Å	Cell parameters from 5083 reflections
c = 11.2170 (2) Å	θ = 4.0–77.6°
α = 83.491 (2)°	µ = 1.14 mm^−1
β = 87.651 (2)°	T = 100 K
γ = 80.623 (2)°	Chunk, pale yellow
V = 811.50 (4) Å^3	0.29 × 0.21 × 0.12 mm

Data collection

Rigaku XtaLAB Synergy Dualflex diffractometer with a HyPix detector	3264 independent reflections
Radiation source: micro-focus sealed X-ray tube	2747 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	Rint = 0.020
ω scans	θmax = 78.7°, θmin = 4.0°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2022)	h = −8→7
Tmin = 0.866, Tmax = 1.000	k = −13→12
8189 measured reflections	l = −13→14

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
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) = 0.121	w = 1/[σ^2(Fo^2) + (0.063P)^2 + 0.0891P] where P = (Fo^2 + 2Fc^2)/3
S = 1.09	(Δ/σ)max = 0.001
3264 reflections	Δρmax = 0.24 e Å^−3
276 parameters	Δρmin = −0.23 e Å^−3
6 restraints	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: dual	Extinction coefficient: 0.0030 (14)

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
O1	0.42580 (14)	0.28912 (12)	0.67200 (9)	0.0602 (3)
O2	0.73679 (15)	0.23081 (15)	0.63183 (11)	0.0819 (4)
O3	0.97403 (19)	0.28117 (18)	0.21730 (15)	0.1011 (5)
O4	0.7890 (2)	0.37951 (17)	0.07750 (12)	0.0951 (5)
O5	0.1315 (2)	0.56467 (19)	0.17510 (13)	0.1061 (6)
O6	0.01239 (16)	0.52545 (14)	0.35069 (12)	0.0815 (4)
N1	0.8189 (2)	0.33985 (15)	0.18135 (14)	0.0681 (4)
N2	0.14539 (18)	0.51684 (14)	0.27830 (12)	0.0614 (3)
C1	0.53808 (17)	0.32933 (12)	0.47140 (11)	0.0421 (3)
C2	0.68942 (18)	0.31182 (13)	0.38792 (13)	0.0484 (3)
H2A	0.813288	0.266509	0.411664	0.058*
C3	0.65780 (19)	0.36108 (14)	0.26983 (12)	0.0485 (3)
C4	0.4824 (2)	0.42859 (14)	0.23032 (12)	0.0499 (3)
H4A	0.463933	0.462671	0.148800	0.060*
C5	0.33492 (18)	0.44403 (13)	0.31563 (12)	0.0450 (3)
C6	0.35780 (17)	0.39613 (12)	0.43486 (11)	0.0425 (3)
H6A	0.252391	0.408565	0.490885	0.051*
C7	0.56866 (18)	0.27902 (14)	0.60226 (12)	0.0493 (3)
O1W	1.12659 (16)	0.16481 (12)	0.60920 (11)	0.0668 (3)
H1W1	1.016 (2)	0.205 (2)	0.608 (2)	0.100*
H1W2	1.196 (3)	0.219 (2)	0.629 (2)	0.100*
N3	0.55128 (15)	0.18930 (11)	0.90663 (11)	0.0477 (3)
H3	0.545 (2)	0.2141 (18)	0.8301 (18)	0.063 (5)*
N4	0.74481 (14)	0.06969 (11)	1.06097 (9)	0.0449 (3)
N5	0.86469 (19)	0.09683 (14)	0.86757 (12)	0.0601 (4)
H51	0.845 (3)	0.1305 (19)	0.793 (2)	0.069 (5)*
H52	0.976 (3)	0.0521 (18)	0.8885 (16)	0.060 (4)*
N6	0.6154 (2)	0.04537 (14)	1.25123 (11)	0.0587 (3)
H61	0.506 (3)	0.0535 (18)	1.3000 (18)	0.068 (5)*
H62	0.726 (3)	−0.006 (2)	1.2701 (18)	0.072 (5)*
N7	0.2350 (2)	0.28554 (15)	0.93328 (16)	0.0684 (4)
H71	0.238 (3)	0.306 (2)	0.860 (2)	0.071 (6)*
H72	0.130 (4)	0.305 (2)	0.977 (2)	0.090 (7)*
C8	0.72079 (18)	0.11756 (13)	0.94736 (11)	0.0443 (3)
C9	0.58988 (18)	0.09333 (12)	1.13700 (11)	0.0445 (3)
C10	0.41238 (19)	0.16638 (13)	1.10030 (12)	0.0488 (3)
H10A	0.307135	0.182244	1.155910	0.059*
C11	0.39469 (18)	0.21426 (13)	0.98216 (12)	0.0471 (3)
O2W	1.2693 (3)	0.0522 (2)	0.40196 (19)	0.1230 (7)
H2W1	1.231 (6)	0.086 (4)	0.464 (3)	0.184*
H2W2	1.230 (6)	−0.016 (3)	0.412 (4)	0.184*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0497 (5)	0.0847 (7)	0.0411 (5)	−0.0033 (5)	0.0006 (4)	0.0040 (5)
O2	0.0409 (5)	0.1272 (11)	0.0648 (7)	0.0001 (6)	−0.0123 (5)	0.0293 (7)
O3	0.0549 (7)	0.1334 (13)	0.1056 (11)	0.0125 (8)	0.0305 (7)	−0.0231 (10)
O4	0.1062 (11)	0.1153 (11)	0.0594 (8)	−0.0163 (9)	0.0380 (7)	−0.0059 (7)
O5	0.0804 (9)	0.1486 (14)	0.0673 (8)	0.0197 (9)	−0.0199 (7)	0.0345 (9)
O6	0.0442 (6)	0.1061 (10)	0.0815 (8)	0.0181 (6)	−0.0001 (5)	0.0008 (7)
N1	0.0637 (8)	0.0743 (9)	0.0672 (9)	−0.0136 (7)	0.0268 (7)	−0.0178 (7)
N2	0.0494 (7)	0.0721 (8)	0.0558 (7)	0.0045 (6)	−0.0105 (5)	0.0063 (6)
C1	0.0358 (6)	0.0470 (6)	0.0418 (6)	−0.0038 (5)	−0.0016 (5)	−0.0020 (5)
C2	0.0347 (6)	0.0523 (7)	0.0557 (8)	−0.0007 (5)	0.0010 (5)	−0.0053 (6)
C3	0.0436 (7)	0.0537 (7)	0.0480 (7)	−0.0069 (5)	0.0112 (5)	−0.0098 (5)
C4	0.0556 (7)	0.0555 (7)	0.0383 (6)	−0.0098 (6)	0.0012 (5)	−0.0025 (5)
C5	0.0392 (6)	0.0492 (7)	0.0438 (6)	−0.0012 (5)	−0.0034 (5)	−0.0010 (5)
C6	0.0352 (6)	0.0489 (6)	0.0411 (6)	−0.0020 (5)	0.0019 (4)	−0.0032 (5)
C7	0.0410 (6)	0.0578 (7)	0.0466 (7)	−0.0057 (5)	−0.0063 (5)	0.0041 (6)
O1W	0.0468 (6)	0.0761 (8)	0.0730 (7)	−0.0003 (5)	−0.0002 (5)	−0.0032 (6)
N3	0.0427 (6)	0.0550 (6)	0.0409 (6)	0.0008 (5)	−0.0053 (4)	0.0026 (5)
N4	0.0372 (5)	0.0529 (6)	0.0403 (5)	0.0022 (4)	−0.0021 (4)	−0.0005 (4)
N5	0.0448 (6)	0.0827 (9)	0.0436 (6)	0.0056 (6)	0.0041 (5)	0.0082 (6)
N6	0.0553 (7)	0.0716 (8)	0.0409 (6)	0.0089 (6)	0.0022 (5)	0.0004 (5)
N7	0.0479 (7)	0.0807 (10)	0.0669 (9)	0.0159 (6)	−0.0110 (6)	0.0001 (7)
C8	0.0391 (6)	0.0493 (7)	0.0421 (6)	−0.0025 (5)	−0.0019 (5)	−0.0007 (5)
C9	0.0439 (6)	0.0466 (6)	0.0413 (6)	−0.0017 (5)	−0.0008 (5)	−0.0061 (5)
C10	0.0404 (6)	0.0543 (7)	0.0487 (7)	0.0021 (5)	0.0025 (5)	−0.0078 (6)
C11	0.0383 (6)	0.0477 (7)	0.0529 (7)	0.0016 (5)	−0.0058 (5)	−0.0064 (5)
O2W	0.1354 (15)	0.1219 (15)	0.1135 (14)	−0.0252 (12)	0.0612 (12)	−0.0376 (12)

Geometric parameters (Å, º)

O1—C7	1.2399 (17)	N3—C8	1.3626 (16)
O2—C7	1.2428 (16)	N3—C11	1.3646 (17)
O3—N1	1.217 (2)	N3—H3	0.87 (2)
O4—N1	1.207 (2)	N4—C8	1.3237 (16)
O5—N2	1.2108 (18)	N4—C9	1.3576 (16)
O6—N2	1.2067 (18)	N5—C8	1.3252 (18)
N1—C3	1.4748 (17)	N5—H51	0.88 (2)
N2—C5	1.4689 (16)	N5—H52	0.865 (19)
C1—C2	1.3859 (18)	N6—C9	1.3315 (17)
C1—C6	1.3916 (16)	N6—H61	0.92 (2)
C1—C7	1.5149 (18)	N6—H62	0.89 (2)
C2—C3	1.380 (2)	N7—C11	1.3389 (18)
C2—H2A	0.9500	N7—H71	0.82 (2)
C3—C4	1.375 (2)	N7—H72	0.87 (3)
C4—C5	1.3790 (19)	C9—C10	1.3994 (17)
C4—H4A	0.9500	C10—C11	1.3670 (19)
C5—C6	1.3814 (18)	C10—H10A	0.9500
C6—H6A	0.9500	O2W—H2W1	0.839 (18)
O1W—H1W1	0.816 (16)	O2W—H2W2	0.806 (18)
O1W—H1W2	0.857 (15)
O4—N1—O3	123.68 (14)	H1W1—O1W—H1W2	104.0 (19)
O4—N1—C3	118.51 (15)	C8—N3—C11	121.01 (11)
O3—N1—C3	117.79 (15)	C8—N3—H3	117.2 (12)
O6—N2—O5	123.50 (13)	C11—N3—H3	121.6 (12)
O6—N2—C5	119.01 (12)	C8—N4—C9	116.85 (10)
O5—N2—C5	117.49 (13)	C8—N5—H51	118.3 (12)
C2—C1—C6	119.57 (12)	C8—N5—H52	121.0 (12)
C2—C1—C7	120.56 (11)	H51—N5—H52	120.8 (18)
C6—C1—C7	119.86 (11)	C9—N6—H61	115.9 (12)
C3—C2—C1	119.12 (12)	C9—N6—H62	118.1 (13)
C3—C2—H2A	120.4	H61—N6—H62	124.6 (19)
C1—C2—H2A	120.4	C11—N7—H71	117.4 (14)
C4—C3—C2	123.10 (12)	C11—N7—H72	120.9 (16)
C4—C3—N1	118.23 (13)	H71—N7—H72	122 (2)
C2—C3—N1	118.66 (13)	N4—C8—N5	120.26 (12)
C3—C4—C5	116.27 (12)	N4—C8—N3	122.75 (11)
C3—C4—H4A	121.9	N5—C8—N3	116.99 (12)
C5—C4—H4A	121.9	N6—C9—N4	116.49 (11)
C4—C5—C6	123.14 (12)	N6—C9—C10	120.58 (12)
C4—C5—N2	118.39 (12)	N4—C9—C10	122.91 (12)
C6—C5—N2	118.45 (11)	C11—C10—C9	118.13 (12)
C5—C6—C1	118.79 (11)	C11—C10—H10A	120.9
C5—C6—H6A	120.6	C9—C10—H10A	120.9
C1—C6—H6A	120.6	N7—C11—N3	116.36 (14)
O1—C7—O2	124.74 (13)	N7—C11—C10	125.29 (14)
O1—C7—C1	118.16 (11)	N3—C11—C10	118.34 (11)
O2—C7—C1	117.10 (12)	H2W1—O2W—H2W2	103 (3)
C6—C1—C2—C3	−0.1 (2)	C2—C1—C6—C5	−0.3 (2)
C7—C1—C2—C3	−178.72 (12)	C7—C1—C6—C5	178.30 (12)
C1—C2—C3—C4	0.7 (2)	C2—C1—C7—O1	−175.10 (13)
C1—C2—C3—N1	−178.91 (12)	C6—C1—C7—O1	6.3 (2)
O4—N1—C3—C4	−1.9 (2)	C2—C1—C7—O2	5.2 (2)
O3—N1—C3—C4	179.27 (15)	C6—C1—C7—O2	−173.43 (14)
O4—N1—C3—C2	177.70 (15)	C9—N4—C8—N5	−179.01 (13)
O3—N1—C3—C2	−1.1 (2)	C9—N4—C8—N3	1.1 (2)
C2—C3—C4—C5	−0.8 (2)	C11—N3—C8—N4	−0.8 (2)
N1—C3—C4—C5	178.80 (12)	C11—N3—C8—N5	179.25 (13)
C3—C4—C5—C6	0.3 (2)	C8—N4—C9—N6	−179.70 (12)
C3—C4—C5—N2	179.24 (12)	C8—N4—C9—C10	−1.1 (2)
O6—N2—C5—C4	176.27 (14)	N6—C9—C10—C11	179.42 (13)
O5—N2—C5—C4	−3.3 (2)	N4—C9—C10—C11	0.9 (2)
O6—N2—C5—C6	−4.8 (2)	C8—N3—C11—N7	−179.94 (13)
O5—N2—C5—C6	175.65 (16)	C8—N3—C11—C10	0.5 (2)
C4—C5—C6—C1	0.2 (2)	C9—C10—C11—N7	179.98 (14)
N2—C5—C6—C1	−178.70 (12)	C9—C10—C11—N3	−0.6 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O6^i	0.95	2.58	3.5201 (17)	171
O1W—H1W1···O2	0.82 (2)	1.94 (2)	2.7043 (15)	156 (2)
O1W—H1W2···O1^ii	0.86 (2)	1.97 (2)	2.7945 (16)	160 (2)
N3—H3···O1	0.87 (2)	2.01 (2)	2.8401 (15)	158.5 (16)
N3—H3···O2	0.87 (2)	2.55 (2)	3.3047 (17)	145.4 (15)
N5—H51···O2	0.88 (2)	2.09 (2)	2.9546 (17)	166.6 (18)
N5—H52···N4^iii	0.865 (19)	2.21 (2)	3.0764 (17)	177.4 (16)
N6—H61···O2W^iv	0.92 (2)	1.97 (2)	2.887 (2)	173.9 (17)
N6—H62···O1W^iii	0.89 (2)	2.18 (2)	2.9619 (17)	146.7 (17)
N7—H71···O1	0.82 (2)	2.45 (2)	3.168 (2)	146.5 (18)
N7—H72···O4^iv	0.87 (3)	2.63 (3)	3.498 (2)	171 (2)
C10—H10A···O3^iv	0.95	2.49	3.3724 (17)	154
O2W—H2W1···O1W	0.84 (2)	1.97 (2)	2.805 (2)	177 (4)
O2W—H2W2···O2^v	0.81 (2)	2.35 (2)	3.068 (3)	148 (4)

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