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In 2,4-diamino-6-methyl-1,3,5-triazin-1-ium (acetoguan­amin­ium) hydrogen phthalate, C4H8N5+·C8H5O4, (I), aceto­guan­aminium hydrogen maleate, C4H8N5+·C4H3O4, (II), and acetoguanaminium 3-hydroxy­picolinate monohydrate, C4H8N5+·C6H4NO3·H2O, (III), the acetoguanaminium cations inter­act with the carboxyl­ate groups of the corresponding anions via a pair of nearly parallel N—H...O hydrogen bonds, forming R22(8) ring motifs. In (II) and (III), N—H...N base-pairing is observed, while there is none in (I). In (II), a series of fused R32(8), R22(8) and R32(8) hydrogen-bonded rings plus fused R22(8), R62(12) and R22(8) ring motifs occur alternately, aggregating into a supra­molecular ladder-like arrangement. In (III), R22(8) motifs occur on either side of a further ring formed by pairs of N—H...O hydrogen bonds, forming an array of three fused hydrogen-bonded rings. In (I) and (II), the anions form a typical intra­molecular O—H...O hydrogen bond with graph set S(7), whereas in (III) an intra­molecular hydrogen bond with graph set S(6) is formed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270110014150/fa3215sup1.cif
Contains datablocks global, I, II, III

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110014150/fa3215Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110014150/fa3215IIsup3.hkl
Contains datablock II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270110014150/fa3215IIIsup4.hkl
Contains datablock III

CCDC references: 693615; 693863; 715740

Computing details top

Data collection: COLLECT (Nonius, 1998) for (I); APEX2 (Bruker, 2004) for (II), (III). Cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998) for (I); APEX2 (Bruker, 2004) and SAINT (Bruker, 2004) for (II); SAINT (Bruker, 2004) for (III). Data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998) for (I); SAINT (Bruker, 2004) and XPREP (Bruker, 2004) for (II); SAINT (Bruker, 2004) for (III). For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

(I) 2,4-diamino-6-methyl-1,3,5-triazinium hydrogen phthalate top
Crystal data top
C4H8N5+·C8H5O4F(000) = 608
Mr = 291.27Dx = 1.504 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2918 reflections
a = 7.0743 (2) Åθ = 3.0–27.5°
b = 23.4468 (5) ŵ = 0.12 mm1
c = 8.1134 (1) ÅT = 120 K
β = 107.063 (1)°Prism, colourless
V = 1286.53 (5) Å30.54 × 0.30 × 0.25 mm
Z = 4
Data collection top
Bruker Nonius [Model?] CCD area-detector
diffractometer
2586 reflections with I > 2σ(I)
Radiation source: Bruker-Nonius FR591 rotating anodeRint = 0.032
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
Detector resolution: 9.091 pixels mm-1h = 96
φ and ω scansk = 3030
14262 measured reflectionsl = 1010
2918 independent reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.127 w = 1/[σ2(Fo2) + (0.077P)2 + 0.3461P]
where P = (Fo2 + 2Fc2)/3
S = 1.12(Δ/σ)max = 0.001
2918 reflectionsΔρmax = 0.39 e Å3
196 parametersΔρmin = 0.54 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.074 (10)
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.79585 (16)0.49071 (4)0.57842 (12)0.0237 (3)
O20.68567 (15)0.49255 (4)0.29478 (12)0.0222 (3)
O30.66971 (15)0.43253 (4)0.05273 (12)0.0231 (3)
O40.73004 (15)0.34393 (4)0.00317 (12)0.0208 (3)
C80.85269 (17)0.40696 (5)0.43681 (16)0.0141 (3)
C90.83451 (17)0.37005 (5)0.29319 (15)0.0138 (3)
C100.91376 (19)0.31492 (5)0.32588 (17)0.0165 (3)
C111.00897 (19)0.29545 (6)0.49086 (18)0.0190 (4)
C121.0274 (2)0.33165 (6)0.63018 (17)0.0198 (3)
C130.94945 (19)0.38637 (6)0.60194 (16)0.0174 (3)
C140.77395 (18)0.46743 (5)0.43656 (16)0.0158 (3)
C150.73816 (18)0.38222 (5)0.10306 (16)0.0157 (3)
N10.65924 (15)0.59420 (4)0.61398 (13)0.0144 (3)
N20.51882 (16)0.60435 (5)0.32053 (13)0.0167 (3)
N30.51377 (15)0.68106 (4)0.49744 (13)0.0135 (3)
N40.51196 (17)0.75246 (5)0.68749 (14)0.0177 (3)
N50.65107 (16)0.66794 (5)0.80597 (13)0.0158 (3)
C20.56246 (17)0.62720 (5)0.47553 (15)0.0129 (3)
C40.55869 (18)0.69951 (5)0.66144 (15)0.0140 (3)
C60.69943 (18)0.61593 (5)0.77510 (16)0.0152 (3)
C70.7995 (2)0.57744 (6)0.92052 (18)0.0229 (4)
H30.671 (4)0.4596 (11)0.166 (3)0.064 (7)*
H100.902000.290400.233200.0200*
H111.059800.258600.507900.0230*
H121.091600.319300.741500.0240*
H130.962000.410200.696200.0210*
H10.694100.559900.598600.0170*
H2A0.458100.624200.231600.0200*
H2B0.551100.569600.308300.0200*
H4A0.454800.773900.601200.0210*
H4B0.538600.765600.790800.0210*
H7A0.913700.596200.994300.0340*
H7B0.839500.543100.875800.0340*
H7C0.709700.568200.985200.0340*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0362 (6)0.0161 (5)0.0172 (5)0.0061 (4)0.0054 (4)0.0029 (4)
O20.0305 (5)0.0156 (5)0.0168 (5)0.0070 (4)0.0013 (4)0.0004 (4)
O30.0343 (6)0.0163 (5)0.0146 (5)0.0058 (4)0.0008 (4)0.0001 (3)
O40.0278 (5)0.0170 (5)0.0157 (5)0.0008 (4)0.0035 (4)0.0038 (3)
C80.0130 (5)0.0119 (6)0.0169 (6)0.0004 (4)0.0034 (4)0.0000 (4)
C90.0123 (5)0.0130 (6)0.0154 (6)0.0012 (4)0.0031 (4)0.0001 (4)
C100.0165 (6)0.0142 (6)0.0190 (6)0.0004 (5)0.0057 (5)0.0020 (5)
C110.0190 (6)0.0139 (6)0.0239 (7)0.0029 (5)0.0058 (5)0.0020 (5)
C120.0204 (6)0.0183 (6)0.0182 (6)0.0022 (5)0.0017 (5)0.0036 (5)
C130.0190 (6)0.0171 (6)0.0145 (6)0.0002 (5)0.0023 (5)0.0012 (5)
C140.0155 (6)0.0132 (6)0.0182 (6)0.0005 (5)0.0042 (4)0.0012 (4)
C150.0155 (6)0.0151 (6)0.0156 (6)0.0014 (5)0.0034 (5)0.0010 (4)
N10.0177 (5)0.0111 (5)0.0136 (5)0.0019 (4)0.0036 (4)0.0004 (4)
N20.0240 (6)0.0124 (5)0.0123 (5)0.0017 (4)0.0031 (4)0.0017 (4)
N30.0168 (5)0.0117 (5)0.0119 (5)0.0004 (4)0.0040 (4)0.0004 (4)
N40.0265 (6)0.0125 (5)0.0129 (5)0.0017 (4)0.0040 (4)0.0020 (4)
N50.0181 (5)0.0150 (5)0.0135 (5)0.0005 (4)0.0034 (4)0.0002 (4)
C20.0134 (5)0.0123 (6)0.0131 (6)0.0017 (4)0.0040 (4)0.0002 (4)
C40.0140 (6)0.0141 (6)0.0143 (6)0.0025 (4)0.0050 (4)0.0002 (4)
C60.0141 (6)0.0172 (6)0.0134 (6)0.0010 (5)0.0028 (4)0.0005 (4)
C70.0275 (7)0.0220 (7)0.0166 (6)0.0066 (6)0.0026 (5)0.0043 (5)
Geometric parameters (Å, º) top
O1—C141.2418 (15)N4—H4A0.8600
O2—C141.2801 (16)C8—C91.4267 (17)
O3—C151.2949 (15)C8—C131.3994 (18)
O4—C151.2341 (15)C8—C141.5231 (17)
O2—H31.28 (2)C9—C151.5194 (17)
O3—H31.12 (2)C9—C101.4030 (17)
N1—C61.3532 (16)C10—C111.3873 (19)
N1—C21.3704 (15)C11—C121.389 (2)
N2—C21.3176 (16)C12—C131.389 (2)
N3—C41.3455 (15)C10—H100.9300
N3—C21.3345 (15)C11—H110.9300
N4—C41.3177 (17)C12—H120.9300
N5—C41.3785 (16)C13—H130.9300
N5—C61.3104 (17)C6—C71.4891 (19)
N1—H10.8600C7—H7A0.9600
N2—H2A0.8600C7—H7B0.9600
N2—H2B0.8600C7—H7C0.9600
N4—H4B0.8600
O1···N12.6587 (14)C10···C6i3.4790 (19)
O1···C14i3.2338 (17)C10···C4iii3.3908 (19)
O2···N22.9074 (15)C11···C2i3.4742 (19)
O3···N2ii3.0541 (14)C11···N3i3.3946 (18)
O3···C7iii3.3974 (18)C12···C2i3.3978 (19)
O4···N4iv2.8748 (15)C13···C2iii3.5036 (19)
O4···N2ii2.9223 (14)C14···C2iii3.4773 (18)
O1···H132.2800C14···C14i3.4190 (18)
O1···H7B2.6400C14···N1iii3.3030 (17)
O1···H11.8000C14···O1i3.2338 (17)
O2···H12.9100C15···N2ii3.3984 (16)
O2···H2B2.0600C15···C6iii3.5154 (19)
O3···H7Ciii2.6100C15···N5iii3.2715 (18)
O3···H2Aii2.5900C15···C7i3.464 (2)
O3···H2Bii2.8900C2···H4Bv2.9100
O4···H4Aiv2.1000C4···H4Bv3.0800
O4···H102.3200C7···H13viii3.0900
O4···H2Aii2.0800C11···H10ix3.0600
O4···H7Ai2.8700C14···H12.6800
N1···C14iii3.3030 (17)C14···H2B2.8900
N1···O12.6587 (14)C15···H2Aii2.6700
N2···O4ii2.9223 (14)C15···H7Ai2.8400
N2···C15ii3.3984 (16)H1···O11.8000
N2···O3ii3.0541 (14)H1···O22.9100
N2···O22.9074 (15)H1···H7B2.2200
N3···C11i3.3946 (18)H1···C142.6800
N3···N4v2.9555 (15)H1···H2B2.2900
N4···N3vi2.9555 (15)H2A···O3ii2.5900
N4···C10iii3.3743 (18)H2A···O4ii2.0800
N4···O4vii2.8748 (15)H2A···C15ii2.6700
N5···C9iii3.4087 (17)H2B···O22.0600
N5···C15iii3.2715 (18)H2B···O3ii2.8900
N3···H4Bv2.1400H2B···C142.8900
C2···C11i3.4742 (19)H2B···H12.2900
C2···C8iii3.3164 (18)H4A···O4vii2.1000
C2···C14iii3.4773 (18)H4B···N3vi2.1400
C2···C13iii3.5036 (19)H4B···C2vi2.9100
C2···C12i3.3978 (19)H4B···C4vi3.0800
C4···C9iii3.3367 (18)H7A···O4i2.8700
C4···C10iii3.3908 (19)H7A···H13viii2.4100
C6···C10i3.4790 (19)H7A···C15i2.8400
C6···C9i3.5153 (18)H7B···H12.2200
C6···C15iii3.5154 (19)H7B···O12.6400
C7···O3iii3.3974 (18)H7C···O3iii2.6100
C7···C15i3.464 (2)H10···O42.3200
C8···C2iii3.3164 (18)H10···C11x3.0600
C9···C6i3.5153 (18)H13···C7viii3.0900
C9···N5iii3.4087 (17)H13···H7Aviii2.4100
C9···C4iii3.3367 (18)H13···O12.2800
C10···N4iii3.3743 (18)
C14—O2—H3110.9 (11)O4—C15—C9119.18 (11)
C15—O3—H3110.3 (13)O3—C15—O4120.40 (11)
C2—N1—C6119.48 (10)O3—C15—C9120.41 (11)
C2—N3—C4116.15 (10)C9—C10—H10119.00
C4—N5—C6114.98 (10)C11—C10—H10119.00
C2—N1—H1120.00C10—C11—H11120.00
C6—N1—H1120.00C12—C11—H11120.00
C2—N2—H2B120.00C11—C12—H12120.00
C2—N2—H2A120.00C13—C12—H12120.00
H2A—N2—H2B120.00C8—C13—H13119.00
H4A—N4—H4B120.00C12—C13—H13119.00
C4—N4—H4A120.00N1—C2—N2118.27 (11)
C4—N4—H4B120.00N2—C2—N3120.97 (11)
C13—C8—C14113.48 (11)N1—C2—N3120.76 (10)
C9—C8—C13118.31 (11)N3—C4—N5125.73 (11)
C9—C8—C14128.19 (11)N4—C4—N5116.62 (11)
C8—C9—C15128.42 (11)N3—C4—N4117.64 (11)
C8—C9—C10117.99 (11)N1—C6—C7116.97 (11)
C10—C9—C15113.60 (10)N5—C6—C7120.17 (11)
C9—C10—C11122.65 (12)N1—C6—N5122.85 (11)
C10—C11—C12119.16 (13)C6—C7—H7A110.00
C11—C12—C13119.50 (12)C6—C7—H7B109.00
C8—C13—C12122.39 (12)C6—C7—H7C109.00
O1—C14—C8117.51 (11)H7A—C7—H7B109.00
O2—C14—C8120.75 (11)H7A—C7—H7C109.00
O1—C14—O2121.73 (11)H7B—C7—H7C109.00
C2—N1—C6—C7178.23 (12)C13—C8—C14—O12.72 (18)
C6—N1—C2—N2177.60 (12)C13—C8—C14—O2178.47 (12)
C6—N1—C2—N32.38 (18)C9—C8—C14—O1175.50 (13)
C2—N1—C6—N50.54 (19)C9—C8—C13—C120.07 (19)
C4—N3—C2—N12.35 (18)C14—C8—C13—C12178.34 (13)
C4—N3—C2—N2177.63 (12)C9—C8—C14—O23.3 (2)
C2—N3—C4—N4179.79 (12)C8—C9—C10—C110.4 (2)
C2—N3—C4—N50.65 (19)C10—C9—C15—O42.68 (18)
C4—N5—C6—C7179.80 (12)C8—C9—C15—O34.4 (2)
C6—N5—C4—N31.05 (19)C8—C9—C15—O4177.29 (13)
C6—N5—C4—N4178.51 (12)C15—C9—C10—C11179.65 (13)
C4—N5—C6—N11.07 (19)C10—C9—C15—O3175.67 (12)
C14—C8—C9—C10177.73 (12)C9—C10—C11—C120.0 (2)
C14—C8—C9—C152.2 (2)C10—C11—C12—C130.4 (2)
C13—C8—C9—C15179.63 (12)C11—C12—C13—C80.3 (2)
C13—C8—C9—C100.41 (18)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z; (iii) x+1, y+1, z+1; (iv) x+1, y1/2, z+1/2; (v) x, y+3/2, z1/2; (vi) x, y+3/2, z+1/2; (vii) x+1, y+1/2, z+1/2; (viii) x+2, y+1, z+2; (ix) x, y+1/2, z+1/2; (x) x, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.802.6587 (14)173
N2—H2A···O3ii0.862.593.0541 (14)115
N2—H2A···O4ii0.862.082.9223 (14)167
N2—H2B···O20.862.062.9074 (15)168
O3—H3···O21.12 (2)1.28 (2)2.3916 (13)175 (2)
N4—H4A···O4vii0.862.102.8748 (15)149
N4—H4B···N3vi0.862.142.9555 (15)158
C10—H10···O40.932.322.6913 (16)104
C13—H13···O10.932.282.6609 (17)104
Symmetry codes: (ii) x+1, y+1, z; (vi) x, y+3/2, z+1/2; (vii) x+1, y+1/2, z+1/2.
(II) 2,4-diamino-6-methyl-1,3,5-triazin-1-ium hydrogen maleate top
Crystal data top
C4H8N5+·C4H3O4Z = 2
Mr = 241.22F(000) = 252
Triclinic, P1Dx = 1.493 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.1921 (3) ÅCell parameters from 3779 reflections
b = 8.2359 (3) Åθ = 2.5–32.4°
c = 9.4775 (4) ŵ = 0.12 mm1
α = 98.287 (2)°T = 293 K
β = 104.656 (2)°Plate-like, colorless
γ = 91.032 (3)°0.22 × 0.18 × 0.16 mm
V = 536.58 (4) Å3
Data collection top
Bruker Kappa APEXII CCD area-detector
diffractometer
3779 independent reflections
Radiation source: fine-focus sealed tube2607 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω and φ scanθmax = 32.4°, θmin = 2.5°
Absorption correction: multi-scan
(Blessing, 1995)
h = 1010
Tmin = 0.974, Tmax = 0.981k = 1212
13516 measured reflectionsl = 1314
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.168H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0865P)2 + 0.1115P]
where P = (Fo2 + 2Fc2)/3
3779 reflections(Δ/σ)max = 0.001
156 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.29101 (16)0.47306 (12)0.57202 (12)0.0358 (3)
N20.23873 (19)0.34969 (14)0.33003 (12)0.0441 (4)
N30.38794 (16)0.20652 (13)0.51373 (11)0.0363 (3)
N40.53588 (19)0.07940 (15)0.70623 (14)0.0457 (4)
N50.43865 (18)0.33738 (14)0.76624 (12)0.0399 (3)
C20.30591 (18)0.34067 (15)0.47085 (13)0.0336 (3)
C40.45226 (19)0.21006 (15)0.65985 (14)0.0353 (3)
C60.35816 (19)0.46583 (16)0.71766 (14)0.0369 (3)
C70.3359 (3)0.61225 (19)0.82164 (17)0.0503 (5)
O10.12718 (18)0.75173 (13)0.48301 (11)0.0526 (4)
O20.07583 (19)0.63810 (13)0.25017 (12)0.0537 (4)
O30.0875 (2)0.69956 (14)0.00684 (11)0.0639 (4)
O40.2559 (2)0.89879 (14)0.07827 (12)0.0575 (4)
C80.0698 (2)0.75762 (15)0.34939 (14)0.0374 (4)
C90.0111 (2)0.91341 (15)0.30547 (14)0.0407 (4)
C100.1043 (2)0.94639 (15)0.17320 (14)0.0406 (4)
C110.1544 (2)0.84338 (17)0.02636 (14)0.0414 (4)
H10.239400.560000.543200.0430*
H2A0.247600.268300.264600.0530*
H2B0.185800.437000.303200.0530*
H4A0.547400.003800.643500.0550*
H4B0.578900.077400.799200.0550*
H7A0.393000.595000.921100.0760*
H7B0.201600.629800.809700.0760*
H7C0.398800.706900.801500.0760*
H30.028500.676300.086800.0960*
H90.006001.001100.382100.0490*
H100.145001.052900.173300.0490*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0449 (6)0.0267 (5)0.0335 (5)0.0108 (4)0.0049 (4)0.0052 (4)
N20.0647 (8)0.0351 (5)0.0295 (5)0.0189 (5)0.0043 (5)0.0073 (4)
N30.0455 (6)0.0304 (5)0.0317 (5)0.0143 (4)0.0054 (4)0.0069 (4)
N40.0604 (7)0.0388 (6)0.0365 (6)0.0232 (5)0.0056 (5)0.0116 (4)
N50.0497 (6)0.0356 (5)0.0315 (5)0.0139 (5)0.0041 (4)0.0055 (4)
C20.0395 (6)0.0286 (5)0.0317 (5)0.0082 (4)0.0061 (5)0.0059 (4)
C40.0406 (6)0.0317 (5)0.0333 (6)0.0115 (5)0.0063 (5)0.0083 (4)
C60.0425 (6)0.0318 (6)0.0338 (6)0.0075 (5)0.0054 (5)0.0037 (4)
C70.0673 (10)0.0378 (7)0.0401 (7)0.0135 (7)0.0076 (7)0.0031 (5)
O10.0796 (8)0.0429 (5)0.0323 (5)0.0219 (5)0.0055 (5)0.0100 (4)
O20.0847 (8)0.0349 (5)0.0366 (5)0.0279 (5)0.0055 (5)0.0051 (4)
O30.1107 (11)0.0448 (6)0.0297 (5)0.0351 (6)0.0051 (6)0.0037 (4)
O40.0817 (8)0.0488 (6)0.0367 (5)0.0225 (6)0.0006 (5)0.0136 (4)
C80.0466 (7)0.0310 (6)0.0340 (6)0.0097 (5)0.0073 (5)0.0079 (4)
C90.0613 (8)0.0281 (5)0.0315 (6)0.0110 (5)0.0090 (6)0.0046 (4)
C100.0589 (8)0.0286 (5)0.0355 (6)0.0156 (5)0.0117 (6)0.0082 (4)
C110.0572 (8)0.0354 (6)0.0318 (6)0.0126 (6)0.0087 (5)0.0098 (5)
Geometric parameters (Å, º) top
O1—C81.2371 (16)N2—H2B0.8600
O2—C81.2690 (17)N2—H2A0.8600
O3—C111.2927 (19)N4—H4B0.8600
O4—C111.2250 (18)N4—H4A0.8600
O3—H30.8200C6—C71.482 (2)
N1—C61.3526 (17)C7—H7C0.9600
N1—C21.3691 (16)C7—H7A0.9600
N2—C21.3129 (16)C7—H7B0.9600
N3—C21.3287 (17)C8—C91.4888 (18)
N3—C41.3403 (16)C9—C101.3319 (18)
N4—C41.3186 (18)C10—C111.4769 (18)
N5—C61.3015 (18)C9—H90.9300
N5—C41.3692 (17)C10—H100.9300
N1—H10.8600
O1···C2i3.3425 (19)C8···C4vii3.467 (2)
O1···C9ii3.4143 (17)C8···N4vii3.308 (2)
O1···N12.7423 (15)C8···O33.1182 (16)
O2···C6i3.321 (2)C9···N4vii3.447 (2)
O2···N22.7852 (16)C9···O1ii3.4143 (17)
O2···C113.0752 (18)C9···C4i3.423 (2)
O2···O32.4375 (15)C10···C11iv3.556 (2)
O3···N2iii3.0650 (15)C10···O4iv3.246 (2)
O3···O22.4375 (15)C10···C4i3.592 (2)
O3···C83.1182 (16)C11···N2iii3.4184 (17)
O4···C10iv3.246 (2)C11···C10iv3.556 (2)
O4···N4v2.8346 (17)C11···C11iv3.545 (2)
O4···N2iii2.9406 (16)C11···O23.0752 (18)
O1···H11.8800C8···H32.4000
O1···H9ii2.5800C8···H2B2.7900
O2···H7Bi2.8400C8···H12.7000
O2···H12.9000C9···H9ii2.9300
O2···H31.6200C9···H32.6100
O2···H2B1.9300C11···H2Aiii2.6900
O3···H2Biii2.8900H1···H7B2.5900
O3···H2Aiii2.5900H1···H7C2.5400
O4···H7Cvi2.8100H1···H2B2.2900
O4···H2Aiii2.0900H1···O11.8800
O4···H4Bv2.1900H1···O22.9000
O4···H4Av2.8900H1···C82.7000
N1···O12.7423 (15)H2A···O3iii2.5900
N1···C2vii3.3968 (17)H2A···O4iii2.0900
N2···O22.7852 (16)H2A···C11iii2.6900
N2···C11iii3.4184 (17)H2B···O21.9300
N2···C6vii3.4089 (19)H2B···O3iii2.8900
N2···O4iii2.9406 (16)H2B···C82.7900
N2···O3iii3.0650 (15)H2B···H12.2900
N3···N4viii3.0660 (17)H3···O21.6200
N4···O4ix2.8346 (17)H3···C92.6100
N4···C9vii3.447 (2)H3···C82.4000
N4···N3viii3.0660 (17)H4A···N3viii2.2100
N4···C8vii3.308 (2)H4A···O4ix2.8900
N3···H4Aviii2.2100H4B···O4ix2.1900
N5···H7Ax2.8700H7A···H7Ax2.5800
C2···N1vii3.3968 (17)H7A···N5x2.8700
C2···O1i3.3425 (19)H7B···H12.5900
C4···C8vii3.467 (2)H7B···O2i2.8400
C4···C10i3.592 (2)H7C···H12.5400
C4···C9i3.423 (2)H7C···O4xi2.8100
C6···O2i3.321 (2)H9···O1ii2.5800
C6···C8i3.425 (2)H9···C9ii2.9300
C6···N2vii3.4089 (19)H9···H9ii2.2600
C8···C6i3.425 (2)
C11—O3—H3109.00N1—C6—C7116.83 (12)
C2—N1—C6119.39 (11)C6—C7—H7B109.00
C2—N3—C4115.87 (11)C6—C7—H7C109.00
C4—N5—C6115.48 (11)H7A—C7—H7B109.00
C2—N1—H1120.00H7A—C7—H7C109.00
C6—N1—H1120.00H7B—C7—H7C109.00
C2—N2—H2A120.00C6—C7—H7A109.00
C2—N2—H2B120.00O1—C8—O2123.24 (13)
H2A—N2—H2B120.00O2—C8—C9119.39 (12)
H4A—N4—H4B120.00O1—C8—C9117.37 (12)
C4—N4—H4A120.00C8—C9—C10129.89 (12)
C4—N4—H4B120.00C9—C10—C11131.29 (12)
N2—C2—N3120.60 (11)O3—C11—C10120.92 (12)
N1—C2—N2118.47 (11)O4—C11—C10118.76 (13)
N1—C2—N3120.94 (11)O3—C11—O4120.28 (12)
N3—C4—N5125.89 (12)C8—C9—H9115.00
N4—C4—N5116.65 (12)C10—C9—H9115.00
N3—C4—N4117.46 (12)C9—C10—H10114.00
N5—C6—C7120.74 (12)C11—C10—H10114.00
N1—C6—N5122.43 (12)
C6—N1—C2—N2179.56 (13)C6—N5—C4—N31.2 (2)
C6—N1—C2—N31.05 (19)C4—N5—C6—N10.5 (2)
C2—N1—C6—C7179.33 (14)C4—N5—C6—C7179.63 (14)
C2—N1—C6—N50.6 (2)O1—C8—C9—C10170.33 (16)
C4—N3—C2—N2179.79 (13)O2—C8—C9—C109.2 (2)
C2—N3—C4—N4179.47 (13)C8—C9—C10—C111.8 (3)
C4—N3—C2—N10.41 (19)C9—C10—C11—O38.3 (3)
C2—N3—C4—N50.7 (2)C9—C10—C11—O4174.06 (16)
C6—N5—C4—N4179.02 (13)
Symmetry codes: (i) x, y+1, z+1; (ii) x, y+2, z+1; (iii) x, y+1, z; (iv) x, y+2, z; (v) x1, y+1, z1; (vi) x1, y, z1; (vii) x+1, y+1, z+1; (viii) x+1, y, z+1; (ix) x+1, y1, z+1; (x) x+1, y+1, z+2; (xi) x+1, y, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.861.882.7423 (15)179
N2—H2A···O3iii0.862.593.0650 (15)116
N2—H2A···O4iii0.862.092.9406 (16)169
N2—H2B···O20.861.932.7852 (16)177
O3—H3···O20.821.622.4375 (15)176
N4—H4A···N3viii0.862.213.0660 (17)173
N4—H4B···O4ix0.862.192.8346 (17)132
C9—H9···O1ii0.932.583.4143 (17)150
Symmetry codes: (ii) x, y+2, z+1; (iii) x, y+1, z; (viii) x+1, y, z+1; (ix) x+1, y1, z+1.
(III) 2,4-diamino-6-methyl-1,3,5-triazinium 3-hydroxypicolinate monohydrate top
Crystal data top
C4H8N5+·C6H4NO3·H2OF(000) = 592
Mr = 282.27Dx = 1.442 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3233 reflections
a = 7.0397 (16) Åθ = 2.8–28.4°
b = 24.680 (5) ŵ = 0.11 mm1
c = 7.5047 (19) ÅT = 296 K
β = 94.462 (7)°Chunk, colourless
V = 1299.9 (5) Å30.56 × 0.42 × 0.28 mm
Z = 4
Data collection top
Bruker APEXII CCD area-detector
diffractometer
3233 independent reflections
Radiation source: fine-focus sealed tube2090 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
φ and ω scansθmax = 28.4°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 99
Tmin = 0.939, Tmax = 0.969k = 3219
10842 measured reflectionsl = 109
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0729P)2 + 0.252P]
where P = (Fo2 + 2Fc2)/3
3233 reflections(Δ/σ)max < 0.001
191 parametersΔρmax = 0.24 e Å3
3 restraintsΔρmin = 0.19 e Å3
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
N10.4970 (2)0.54462 (5)0.29495 (19)0.0396 (4)
N20.7324 (2)0.48069 (6)0.3382 (2)0.0488 (5)
N30.4543 (2)0.45687 (5)0.1802 (2)0.0412 (5)
N40.1705 (2)0.43923 (6)0.0267 (2)0.0495 (5)
N50.2094 (2)0.52480 (6)0.1388 (2)0.0417 (5)
C20.5628 (2)0.49280 (6)0.2702 (2)0.0381 (5)
C40.2825 (2)0.47337 (6)0.1182 (2)0.0392 (5)
C60.3210 (2)0.55867 (7)0.2275 (2)0.0396 (5)
C70.2589 (3)0.61504 (7)0.2581 (3)0.0514 (6)
O10.9117 (2)0.56798 (5)0.5168 (2)0.0673 (5)
O20.6960 (2)0.63282 (6)0.4812 (2)0.0587 (5)
O30.7440 (2)0.72142 (6)0.6472 (2)0.0698 (6)
N61.1557 (2)0.63392 (6)0.7091 (2)0.0506 (5)
C80.9812 (3)0.65177 (6)0.6571 (2)0.0407 (5)
C90.9204 (3)0.70349 (7)0.7004 (3)0.0492 (6)
C101.0479 (4)0.73694 (8)0.7986 (3)0.0654 (8)
C111.2240 (4)0.71853 (9)0.8486 (3)0.0693 (9)
C121.2752 (3)0.66644 (9)0.8022 (3)0.0608 (7)
C130.8553 (3)0.61401 (7)0.5446 (3)0.0462 (6)
O1W0.7024 (3)0.66313 (6)0.1112 (3)0.0789 (8)
H10.568200.567900.353300.0470*
H2A0.776900.448600.325300.0590*
H2B0.800500.504700.396300.0590*
H4A0.209000.406800.007900.0590*
H4B0.058700.449300.014600.0590*
H7A0.129300.619500.210500.0770*
H7B0.339100.639700.199500.0770*
H7C0.268000.622400.384000.0770*
H30.688100.698400.584000.1050*
H101.012000.771700.829700.0780*
H111.310900.740600.913900.0830*
H121.397000.654000.837600.0730*
H1W0.710 (4)0.6949 (7)0.095 (4)0.097 (10)*
H2W0.714 (5)0.6586 (13)0.220 (3)0.136 (16)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0392 (8)0.0302 (7)0.0483 (8)0.0028 (6)0.0028 (6)0.0039 (6)
N20.0472 (9)0.0336 (7)0.0630 (10)0.0021 (6)0.0121 (8)0.0024 (6)
N30.0422 (8)0.0290 (7)0.0515 (9)0.0013 (6)0.0029 (7)0.0003 (6)
N40.0430 (9)0.0343 (7)0.0695 (11)0.0032 (6)0.0069 (8)0.0071 (7)
N50.0360 (8)0.0342 (7)0.0544 (9)0.0001 (6)0.0002 (7)0.0029 (6)
C20.0425 (9)0.0296 (8)0.0417 (9)0.0015 (7)0.0002 (7)0.0035 (6)
C40.0397 (9)0.0322 (8)0.0456 (9)0.0037 (7)0.0032 (8)0.0015 (7)
C60.0389 (9)0.0337 (8)0.0462 (10)0.0029 (7)0.0038 (8)0.0000 (7)
C70.0486 (11)0.0373 (9)0.0680 (13)0.0031 (8)0.0019 (9)0.0076 (8)
O10.0675 (10)0.0387 (7)0.0919 (11)0.0034 (7)0.0184 (8)0.0219 (7)
O20.0516 (8)0.0495 (8)0.0720 (10)0.0006 (6)0.0136 (7)0.0033 (7)
O30.0686 (10)0.0400 (8)0.0990 (13)0.0121 (7)0.0052 (9)0.0107 (7)
N60.0543 (10)0.0410 (8)0.0541 (9)0.0004 (7)0.0109 (8)0.0045 (7)
C80.0501 (10)0.0308 (8)0.0406 (9)0.0014 (7)0.0010 (8)0.0004 (7)
C90.0611 (12)0.0350 (9)0.0513 (11)0.0018 (8)0.0028 (9)0.0011 (8)
C100.0912 (18)0.0379 (10)0.0657 (14)0.0029 (11)0.0027 (12)0.0131 (9)
C110.0868 (18)0.0515 (12)0.0656 (14)0.0159 (12)0.0187 (13)0.0116 (10)
C120.0620 (13)0.0555 (12)0.0618 (13)0.0048 (10)0.0154 (11)0.0058 (10)
C130.0496 (11)0.0374 (9)0.0507 (11)0.0031 (8)0.0026 (8)0.0001 (8)
O1W0.1168 (16)0.0356 (8)0.0838 (14)0.0087 (9)0.0039 (11)0.0032 (8)
Geometric parameters (Å, º) top
O1—C131.227 (2)N4—H4A0.8600
O2—C131.271 (3)N4—H4B0.8600
O3—C91.349 (3)N6—C121.322 (3)
O3—H30.8200N6—C81.335 (2)
O1W—H1W0.796 (18)C6—C71.482 (2)
O1W—H2W0.82 (2)C7—H7B0.9600
N1—C21.378 (2)C7—H7A0.9600
N1—C61.347 (2)C7—H7C0.9600
N2—C21.296 (2)C8—C131.500 (3)
N3—C41.326 (2)C8—C91.393 (2)
N3—C21.321 (2)C9—C101.388 (3)
N4—C41.311 (2)C10—C111.346 (4)
N5—C61.295 (2)C11—C121.387 (3)
N5—C41.383 (2)C10—H100.9300
N1—H10.8600C11—H110.9300
N2—H2A0.8600C12—H120.9300
N2—H2B0.8600
O1···N62.701 (2)C10···C9v3.533 (3)
O1···N2i2.912 (2)C13···C4ii3.518 (3)
O1···C4ii3.316 (2)C6···H4Bvii3.0100
O1···N22.787 (2)C8···H2Ai3.0000
O1W···O3iii2.875 (2)C8···H7Cviii3.0700
O1W···O22.880 (3)C9···H10iii2.9700
O1W···N4iv2.898 (2)C9···H1Wv2.99 (2)
O2···O1W2.880 (3)C12···H7Bix3.0500
O2···O32.526 (2)C12···H2Ai3.0100
O2···N12.890 (2)C13···H12.6400
O2···C73.415 (3)C13···H2W2.79 (3)
O3···O1Wv2.875 (2)C13···H32.4200
O3···O22.526 (2)C13···H2B2.9300
O1···H2Bi2.7500H1···H7C2.5300
O1···H2Ai2.4400H1···O12.6300
O1···H2B1.9400H1···H2B2.2600
O1···H12.6300H1···O22.0400
O1W···H4Aiv2.0600H1···C132.6400
O1W···H7B2.7500H1W···C9iii2.99 (2)
O1W···H12vi2.8600H1W···O3iii2.112 (18)
O2···H31.8000H2A···C12i3.0100
O2···H12.0400H2A···O1i2.4400
O2···H2W2.07 (2)H2A···N6i2.1100
O3···H1Wv2.112 (18)H2A···C8i3.0000
N1···C2ii3.449 (2)H2B···O1i2.7500
N1···O22.890 (2)H2B···O11.9400
N2···O12.787 (2)H2B···H12.2600
N2···C6ii3.449 (2)H2B···C132.9300
N2···O1i2.912 (2)H2W···C132.79 (3)
N2···N6i2.965 (2)H2W···O22.07 (2)
N4···O1Wiv2.898 (2)H2W···H4Aiv2.4400
N4···N5vii2.994 (2)H3···C132.4200
N5···N4vii2.994 (2)H3···O21.8000
N6···N2i2.965 (2)H4A···H2Wiv2.4400
N6···O12.701 (2)H4A···O1Wiv2.0600
N3···H12i2.9400H4B···H7Avii2.5500
N5···H4Bvii2.1400H4B···N5vii2.1400
N6···H7Cviii2.6400H4B···C6vii3.0100
N6···H2Ai2.1100H7A···H4Bvii2.5500
C2···N1ii3.449 (2)H7B···C12vi3.0500
C2···C4iv3.298 (2)H7B···O1W2.7500
C4···O1ii3.316 (2)H7C···H12.5300
C4···C2iv3.298 (2)H7C···C8x3.0700
C4···C13ii3.518 (3)H7C···N6x2.6400
C6···N2ii3.449 (2)H10···C9v2.9700
C7···O23.415 (3)H12···O1Wix2.8600
C9···C10iii3.533 (3)H12···N3i2.9400
C9—O3—H3109.00C6—C7—H7B109.00
H1W—O1W—H2W106 (3)C6—C7—H7C109.00
C2—N1—C6119.83 (14)H7A—C7—H7B109.00
C2—N3—C4116.65 (13)H7B—C7—H7C110.00
C4—N5—C6115.70 (14)H7A—C7—H7C109.00
C6—N1—H1120.00N6—C8—C9121.80 (17)
C2—N1—H1120.00N6—C8—C13116.72 (15)
C2—N2—H2A120.00C9—C8—C13121.46 (18)
C2—N2—H2B120.00O3—C9—C8121.61 (18)
H2A—N2—H2B120.00C8—C9—C10118.1 (2)
H4A—N4—H4B120.00O3—C9—C10120.28 (18)
C4—N4—H4B120.00C9—C10—C11119.4 (2)
C4—N4—H4A120.00C10—C11—C12119.7 (2)
C8—N6—C12119.17 (16)N6—C12—C11121.9 (2)
N1—C2—N3120.32 (13)O2—C13—C8116.69 (16)
N2—C2—N3121.64 (14)O1—C13—O2124.21 (19)
N1—C2—N2118.03 (14)O1—C13—C8119.09 (18)
N3—C4—N4118.78 (14)C11—C10—H10120.00
N3—C4—N5125.45 (14)C9—C10—H10120.00
N4—C4—N5115.76 (14)C10—C11—H11120.00
N5—C6—C7120.74 (15)C12—C11—H11120.00
N1—C6—C7117.22 (15)N6—C12—H12119.00
N1—C6—N5122.04 (15)C11—C12—H12119.00
C6—C7—H7A109.00
C6—N1—C2—N2179.51 (15)C8—N6—C12—C110.5 (3)
C6—N1—C2—N30.2 (2)N6—C8—C9—O3179.85 (17)
C2—N1—C6—N50.0 (2)N6—C8—C9—C100.8 (3)
C2—N1—C6—C7179.78 (15)C13—C8—C9—O31.8 (3)
C4—N3—C2—N10.5 (2)C13—C8—C9—C10177.28 (19)
C4—N3—C2—N2179.24 (15)N6—C8—C13—O15.2 (3)
C2—N3—C4—N4179.40 (15)N6—C8—C13—O2173.62 (17)
C2—N3—C4—N50.6 (2)C9—C8—C13—O1176.69 (19)
C6—N5—C4—N30.4 (2)C9—C8—C13—O24.5 (3)
C6—N5—C4—N4179.25 (14)O3—C9—C10—C11179.2 (2)
C4—N5—C6—N10.1 (2)C8—C9—C10—C110.1 (3)
C4—N5—C6—C7179.86 (15)C9—C10—C11—C120.3 (3)
C12—N6—C8—C90.9 (3)C10—C11—C12—N60.2 (3)
C12—N6—C8—C13177.21 (18)
Symmetry codes: (i) x+2, y+1, z+1; (ii) x+1, y+1, z+1; (iii) x, y+3/2, z1/2; (iv) x+1, y+1, z; (v) x, y+3/2, z+1/2; (vi) x1, y, z1; (vii) x, y+1, z; (viii) x+1, y, z; (ix) x+1, y, z+1; (x) x1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O20.862.042.890 (2)169
O1W—H1W···O3iii0.796 (18)2.112 (18)2.875 (2)161 (3)
N2—H2A···O1i0.862.442.912 (2)115
N2—H2A···N6i0.862.112.965 (2)172
N2—H2B···O10.861.942.787 (2)169
O1W—H2W···O20.82 (2)2.07 (2)2.880 (3)166 (3)
O3—H3···O20.821.802.526 (2)147
N4—H4A···O1Wiv0.862.062.898 (2)164
N4—H4B···N5vii0.862.142.994 (2)175
Symmetry codes: (i) x+2, y+1, z+1; (iii) x, y+3/2, z1/2; (iv) x+1, y+1, z; (vii) x, y+1, z.
Selected geometric parameters for (I), (II) and (III) (Å, °) top
(I)(II)(III)
N1—C21.3704 (15)1.3691 (16)1.378 (2)
N1—C61.3532 (16)1.3526 (17)1.347 (2)
N3—C41.3455 (15)1.3403 (16)1.326 (2)
N3—C21.3345 (15)1.3287 (17)1.321 (2)
N5—C41.3785 (16)1.3692 (17)1.383 (2)
N5—C61.3104 (17)1.3015 (18)1.295 (2)
C2—N1—C6119.48 (10)119.39 (11)119.83 (14)
C2—N3—C4116.15 (10)115.87 (11)116.65 (13)
C4—N5—C6114.98 (10)115.48 (11)115.70 (14)
 

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