Charge-assisted hydrogen-bonded supra­molecular networks in acetoguanaminium hydrogen phthalate, acetoguanaminium hydrogen maleate and acetoguanaminium 3-hydroxy­picolinate monohydrate

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.

Computing details

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

Crystal data

C4H8N5^+·C8H5O4^−	F(000) = 608
Mr = 291.27	Dx = 1.504 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2918 reflections
a = 7.0743 (2) Å	θ = 3.0–27.5°
b = 23.4468 (5) Å	µ = 0.12 mm^−1
c = 8.1134 (1) Å	T = 120 K
β = 107.063 (1)°	Prism, colourless
V = 1286.53 (5) Å^3	0.54 × 0.30 × 0.25 mm
Z = 4

Data collection

Bruker Nonius [Model?] CCD area-detector diffractometer	2586 reflections with I > 2σ(I)
Radiation source: Bruker-Nonius FR591 rotating anode	Rint = 0.032
Graphite monochromator	θmax = 27.5°, θmin = 3.0°
Detector resolution: 9.091 pixels mm^-1	h = −9→6
φ and ω scans	k = −30→30
14262 measured reflections	l = −10→10
2918 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.077P)^2 + 0.3461P] where P = (Fo^2 + 2Fc^2)/3
S = 1.12	(Δ/σ)max = 0.001
2918 reflections	Δρmax = 0.39 e Å^−3
196 parameters	Δρmin = −0.54 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC^2Λ^3/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.074 (10)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.79585 (16)	0.49071 (4)	0.57842 (12)	0.0237 (3)
O2	0.68567 (15)	0.49255 (4)	0.29478 (12)	0.0222 (3)
O3	0.66971 (15)	0.43253 (4)	0.05273 (12)	0.0231 (3)
O4	0.73004 (15)	0.34393 (4)	−0.00317 (12)	0.0208 (3)
C8	0.85269 (17)	0.40696 (5)	0.43681 (16)	0.0141 (3)
C9	0.83451 (17)	0.37005 (5)	0.29319 (15)	0.0138 (3)
C10	0.91376 (19)	0.31492 (5)	0.32588 (17)	0.0165 (3)
C11	1.00897 (19)	0.29545 (6)	0.49086 (18)	0.0190 (4)
C12	1.0274 (2)	0.33165 (6)	0.63018 (17)	0.0198 (3)
C13	0.94945 (19)	0.38637 (6)	0.60194 (16)	0.0174 (3)
C14	0.77395 (18)	0.46743 (5)	0.43656 (16)	0.0158 (3)
C15	0.73816 (18)	0.38222 (5)	0.10306 (16)	0.0157 (3)
N1	0.65924 (15)	0.59420 (4)	0.61398 (13)	0.0144 (3)
N2	0.51882 (16)	0.60435 (5)	0.32053 (13)	0.0167 (3)
N3	0.51377 (15)	0.68106 (4)	0.49744 (13)	0.0135 (3)
N4	0.51196 (17)	0.75246 (5)	0.68749 (14)	0.0177 (3)
N5	0.65107 (16)	0.66794 (5)	0.80597 (13)	0.0158 (3)
C2	0.56246 (17)	0.62720 (5)	0.47553 (15)	0.0129 (3)
C4	0.55869 (18)	0.69951 (5)	0.66144 (15)	0.0140 (3)
C6	0.69943 (18)	0.61593 (5)	0.77510 (16)	0.0152 (3)
C7	0.7995 (2)	0.57744 (6)	0.92052 (18)	0.0229 (4)
H3	0.671 (4)	0.4596 (11)	0.166 (3)	0.064 (7)*
H10	0.90200	0.29040	0.23320	0.0200*
H11	1.05980	0.25860	0.50790	0.0230*
H12	1.09160	0.31930	0.74150	0.0240*
H13	0.96200	0.41020	0.69620	0.0210*
H1	0.69410	0.55990	0.59860	0.0170*
H2A	0.45810	0.62420	0.23160	0.0200*
H2B	0.55110	0.56960	0.30830	0.0200*
H4A	0.45480	0.77390	0.60120	0.0210*
H4B	0.53860	0.76560	0.79080	0.0210*
H7A	0.91370	0.59620	0.99430	0.0340*
H7B	0.83950	0.54310	0.87580	0.0340*
H7C	0.70970	0.56820	0.98520	0.0340*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0362 (6)	0.0161 (5)	0.0172 (5)	0.0061 (4)	0.0054 (4)	−0.0029 (4)
O2	0.0305 (5)	0.0156 (5)	0.0168 (5)	0.0070 (4)	0.0013 (4)	−0.0004 (4)
O3	0.0343 (6)	0.0163 (5)	0.0146 (5)	0.0058 (4)	0.0008 (4)	−0.0001 (3)
O4	0.0278 (5)	0.0170 (5)	0.0157 (5)	−0.0008 (4)	0.0035 (4)	−0.0038 (3)
C8	0.0130 (5)	0.0119 (6)	0.0169 (6)	−0.0004 (4)	0.0034 (4)	0.0000 (4)
C9	0.0123 (5)	0.0130 (6)	0.0154 (6)	−0.0012 (4)	0.0031 (4)	−0.0001 (4)
C10	0.0165 (6)	0.0142 (6)	0.0190 (6)	−0.0004 (5)	0.0057 (5)	−0.0020 (5)
C11	0.0190 (6)	0.0139 (6)	0.0239 (7)	0.0029 (5)	0.0058 (5)	0.0020 (5)
C12	0.0204 (6)	0.0183 (6)	0.0182 (6)	0.0022 (5)	0.0017 (5)	0.0036 (5)
C13	0.0190 (6)	0.0171 (6)	0.0145 (6)	0.0002 (5)	0.0023 (5)	−0.0012 (5)
C14	0.0155 (6)	0.0132 (6)	0.0182 (6)	−0.0005 (5)	0.0042 (4)	−0.0012 (4)
C15	0.0155 (6)	0.0151 (6)	0.0156 (6)	−0.0014 (5)	0.0034 (5)	−0.0010 (4)
N1	0.0177 (5)	0.0111 (5)	0.0136 (5)	0.0019 (4)	0.0036 (4)	0.0004 (4)
N2	0.0240 (6)	0.0124 (5)	0.0123 (5)	0.0017 (4)	0.0031 (4)	−0.0017 (4)
N3	0.0168 (5)	0.0117 (5)	0.0119 (5)	−0.0004 (4)	0.0040 (4)	−0.0004 (4)
N4	0.0265 (6)	0.0125 (5)	0.0129 (5)	0.0017 (4)	0.0040 (4)	−0.0020 (4)
N5	0.0181 (5)	0.0150 (5)	0.0135 (5)	0.0005 (4)	0.0034 (4)	−0.0002 (4)
C2	0.0134 (5)	0.0123 (6)	0.0131 (6)	−0.0017 (4)	0.0040 (4)	0.0002 (4)
C4	0.0140 (6)	0.0141 (6)	0.0143 (6)	−0.0025 (4)	0.0050 (4)	−0.0002 (4)
C6	0.0141 (6)	0.0172 (6)	0.0134 (6)	−0.0010 (5)	0.0028 (4)	0.0005 (4)
C7	0.0275 (7)	0.0220 (7)	0.0166 (6)	0.0066 (6)	0.0026 (5)	0.0043 (5)

Geometric parameters (Å, º)

O1—C14	1.2418 (15)	N4—H4A	0.8600
O2—C14	1.2801 (16)	C8—C9	1.4267 (17)
O3—C15	1.2949 (15)	C8—C13	1.3994 (18)
O4—C15	1.2341 (15)	C8—C14	1.5231 (17)
O2—H3	1.28 (2)	C9—C15	1.5194 (17)
O3—H3	1.12 (2)	C9—C10	1.4030 (17)
N1—C6	1.3532 (16)	C10—C11	1.3873 (19)
N1—C2	1.3704 (15)	C11—C12	1.389 (2)
N2—C2	1.3176 (16)	C12—C13	1.389 (2)
N3—C4	1.3455 (15)	C10—H10	0.9300
N3—C2	1.3345 (15)	C11—H11	0.9300
N4—C4	1.3177 (17)	C12—H12	0.9300
N5—C4	1.3785 (16)	C13—H13	0.9300
N5—C6	1.3104 (17)	C6—C7	1.4891 (19)
N1—H1	0.8600	C7—H7A	0.9600
N2—H2A	0.8600	C7—H7B	0.9600
N2—H2B	0.8600	C7—H7C	0.9600
N4—H4B	0.8600
O1···N1	2.6587 (14)	C10···C6^i	3.4790 (19)
O1···C14^i	3.2338 (17)	C10···C4^iii	3.3908 (19)
O2···N2	2.9074 (15)	C11···C2^i	3.4742 (19)
O3···N2^ii	3.0541 (14)	C11···N3^i	3.3946 (18)
O3···C7^iii	3.3974 (18)	C12···C2^i	3.3978 (19)
O4···N4^iv	2.8748 (15)	C13···C2^iii	3.5036 (19)
O4···N2^ii	2.9223 (14)	C14···C2^iii	3.4773 (18)
O1···H13	2.2800	C14···C14^i	3.4190 (18)
O1···H7B	2.6400	C14···N1^iii	3.3030 (17)
O1···H1	1.8000	C14···O1^i	3.2338 (17)
O2···H1	2.9100	C15···N2^ii	3.3984 (16)
O2···H2B	2.0600	C15···C6^iii	3.5154 (19)
O3···H7C^iii	2.6100	C15···N5^iii	3.2715 (18)
O3···H2A^ii	2.5900	C15···C7^i	3.464 (2)
O3···H2B^ii	2.8900	C2···H4B^v	2.9100
O4···H4A^iv	2.1000	C4···H4B^v	3.0800
O4···H10	2.3200	C7···H13^viii	3.0900
O4···H2A^ii	2.0800	C11···H10^ix	3.0600
O4···H7A^i	2.8700	C14···H1	2.6800
N1···C14^iii	3.3030 (17)	C14···H2B	2.8900
N1···O1	2.6587 (14)	C15···H2A^ii	2.6700
N2···O4^ii	2.9223 (14)	C15···H7A^i	2.8400
N2···C15^ii	3.3984 (16)	H1···O1	1.8000
N2···O3^ii	3.0541 (14)	H1···O2	2.9100
N2···O2	2.9074 (15)	H1···H7B	2.2200
N3···C11^i	3.3946 (18)	H1···C14	2.6800
N3···N4^v	2.9555 (15)	H1···H2B	2.2900
N4···N3^vi	2.9555 (15)	H2A···O3^ii	2.5900
N4···C10^iii	3.3743 (18)	H2A···O4^ii	2.0800
N4···O4^vii	2.8748 (15)	H2A···C15^ii	2.6700
N5···C9^iii	3.4087 (17)	H2B···O2	2.0600
N5···C15^iii	3.2715 (18)	H2B···O3^ii	2.8900
N3···H4B^v	2.1400	H2B···C14	2.8900
C2···C11^i	3.4742 (19)	H2B···H1	2.2900
C2···C8^iii	3.3164 (18)	H4A···O4^vii	2.1000
C2···C14^iii	3.4773 (18)	H4B···N3^vi	2.1400
C2···C13^iii	3.5036 (19)	H4B···C2^vi	2.9100
C2···C12^i	3.3978 (19)	H4B···C4^vi	3.0800
C4···C9^iii	3.3367 (18)	H7A···O4^i	2.8700
C4···C10^iii	3.3908 (19)	H7A···H13^viii	2.4100
C6···C10^i	3.4790 (19)	H7A···C15^i	2.8400
C6···C9^i	3.5153 (18)	H7B···H1	2.2200
C6···C15^iii	3.5154 (19)	H7B···O1	2.6400
C7···O3^iii	3.3974 (18)	H7C···O3^iii	2.6100
C7···C15^i	3.464 (2)	H10···O4	2.3200
C8···C2^iii	3.3164 (18)	H10···C11^x	3.0600
C9···C6^i	3.5153 (18)	H13···C7^viii	3.0900
C9···N5^iii	3.4087 (17)	H13···H7A^viii	2.4100
C9···C4^iii	3.3367 (18)	H13···O1	2.2800
C10···N4^iii	3.3743 (18)
C14—O2—H3	110.9 (11)	O4—C15—C9	119.18 (11)
C15—O3—H3	110.3 (13)	O3—C15—O4	120.40 (11)
C2—N1—C6	119.48 (10)	O3—C15—C9	120.41 (11)
C2—N3—C4	116.15 (10)	C9—C10—H10	119.00
C4—N5—C6	114.98 (10)	C11—C10—H10	119.00
C2—N1—H1	120.00	C10—C11—H11	120.00
C6—N1—H1	120.00	C12—C11—H11	120.00
C2—N2—H2B	120.00	C11—C12—H12	120.00
C2—N2—H2A	120.00	C13—C12—H12	120.00
H2A—N2—H2B	120.00	C8—C13—H13	119.00
H4A—N4—H4B	120.00	C12—C13—H13	119.00
C4—N4—H4A	120.00	N1—C2—N2	118.27 (11)
C4—N4—H4B	120.00	N2—C2—N3	120.97 (11)
C13—C8—C14	113.48 (11)	N1—C2—N3	120.76 (10)
C9—C8—C13	118.31 (11)	N3—C4—N5	125.73 (11)
C9—C8—C14	128.19 (11)	N4—C4—N5	116.62 (11)
C8—C9—C15	128.42 (11)	N3—C4—N4	117.64 (11)
C8—C9—C10	117.99 (11)	N1—C6—C7	116.97 (11)
C10—C9—C15	113.60 (10)	N5—C6—C7	120.17 (11)
C9—C10—C11	122.65 (12)	N1—C6—N5	122.85 (11)
C10—C11—C12	119.16 (13)	C6—C7—H7A	110.00
C11—C12—C13	119.50 (12)	C6—C7—H7B	109.00
C8—C13—C12	122.39 (12)	C6—C7—H7C	109.00
O1—C14—C8	117.51 (11)	H7A—C7—H7B	109.00
O2—C14—C8	120.75 (11)	H7A—C7—H7C	109.00
O1—C14—O2	121.73 (11)	H7B—C7—H7C	109.00
C2—N1—C6—C7	178.23 (12)	C13—C8—C14—O1	−2.72 (18)
C6—N1—C2—N2	−177.60 (12)	C13—C8—C14—O2	178.47 (12)
C6—N1—C2—N3	2.38 (18)	C9—C8—C14—O1	175.50 (13)
C2—N1—C6—N5	−0.54 (19)	C9—C8—C13—C12	−0.07 (19)
C4—N3—C2—N1	−2.35 (18)	C14—C8—C13—C12	178.34 (13)
C4—N3—C2—N2	177.63 (12)	C9—C8—C14—O2	−3.3 (2)
C2—N3—C4—N4	−179.79 (12)	C8—C9—C10—C11	−0.4 (2)
C2—N3—C4—N5	0.65 (19)	C10—C9—C15—O4	2.68 (18)
C4—N5—C6—C7	−179.80 (12)	C8—C9—C15—O3	4.4 (2)
C6—N5—C4—N3	1.05 (19)	C8—C9—C15—O4	−177.29 (13)
C6—N5—C4—N4	−178.51 (12)	C15—C9—C10—C11	179.65 (13)
C4—N5—C6—N1	−1.07 (19)	C10—C9—C15—O3	−175.67 (12)
C14—C8—C9—C10	−177.73 (12)	C9—C10—C11—C12	0.0 (2)
C14—C8—C9—C15	2.2 (2)	C10—C11—C12—C13	0.4 (2)
C13—C8—C9—C15	−179.63 (12)	C11—C12—C13—C8	−0.3 (2)
C13—C8—C9—C10	0.41 (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, y−1/2, −z+1/2; (v) x, −y+3/2, z−1/2; (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, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.80	2.6587 (14)	173
N2—H2A···O3^ii	0.86	2.59	3.0541 (14)	115
N2—H2A···O4^ii	0.86	2.08	2.9223 (14)	167
N2—H2B···O2	0.86	2.06	2.9074 (15)	168
O3—H3···O2	1.12 (2)	1.28 (2)	2.3916 (13)	175 (2)
N4—H4A···O4^vii	0.86	2.10	2.8748 (15)	149
N4—H4B···N3^vi	0.86	2.14	2.9555 (15)	158
C10—H10···O4	0.93	2.32	2.6913 (16)	104
C13—H13···O1	0.93	2.28	2.6609 (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

Crystal data

C4H8N5^+·C4H3O4^−	Z = 2
Mr = 241.22	F(000) = 252
Triclinic, P1	Dx = 1.493 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.1921 (3) Å	Cell parameters from 3779 reflections
b = 8.2359 (3) Å	θ = 2.5–32.4°
c = 9.4775 (4) Å	µ = 0.12 mm^−1
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) Å^3

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer	3779 independent reflections
Radiation source: fine-focus sealed tube	2607 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
ω and φ scan	θmax = 32.4°, θmin = 2.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −10→10
Tmin = 0.974, Tmax = 0.981	k = −12→12
13516 measured reflections	l = −13→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.168	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0865P)^2 + 0.1115P] where P = (Fo^2 + 2Fc^2)/3
3779 reflections	(Δ/σ)max = 0.001
156 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.29101 (16)	0.47306 (12)	0.57202 (12)	0.0358 (3)
N2	0.23873 (19)	0.34969 (14)	0.33003 (12)	0.0441 (4)
N3	0.38794 (16)	0.20652 (13)	0.51373 (11)	0.0363 (3)
N4	0.53588 (19)	0.07940 (15)	0.70623 (14)	0.0457 (4)
N5	0.43865 (18)	0.33738 (14)	0.76624 (12)	0.0399 (3)
C2	0.30591 (18)	0.34067 (15)	0.47085 (13)	0.0336 (3)
C4	0.45226 (19)	0.21006 (15)	0.65985 (14)	0.0353 (3)
C6	0.35816 (19)	0.46583 (16)	0.71766 (14)	0.0369 (3)
C7	0.3359 (3)	0.61225 (19)	0.82164 (17)	0.0503 (5)
O1	0.12718 (18)	0.75173 (13)	0.48301 (11)	0.0526 (4)
O2	0.07583 (19)	0.63810 (13)	0.25017 (12)	0.0537 (4)
O3	−0.0875 (2)	0.69956 (14)	0.00684 (11)	0.0639 (4)
O4	−0.2559 (2)	0.89879 (14)	−0.07827 (12)	0.0575 (4)
C8	0.0698 (2)	0.75762 (15)	0.34939 (14)	0.0374 (4)
C9	−0.0111 (2)	0.91341 (15)	0.30547 (14)	0.0407 (4)
C10	−0.1043 (2)	0.94639 (15)	0.17320 (14)	0.0406 (4)
C11	−0.1544 (2)	0.84338 (17)	0.02636 (14)	0.0414 (4)
H1	0.23940	0.56000	0.54320	0.0430*
H2A	0.24760	0.26830	0.26460	0.0530*
H2B	0.18580	0.43700	0.30320	0.0530*
H4A	0.54740	−0.00380	0.64350	0.0550*
H4B	0.57890	0.07740	0.79920	0.0550*
H7A	0.39300	0.59500	0.92110	0.0760*
H7B	0.20160	0.62980	0.80970	0.0760*
H7C	0.39880	0.70690	0.80150	0.0760*
H3	−0.02850	0.67630	0.08680	0.0960*
H9	0.00600	1.00110	0.38210	0.0490*
H10	−0.14500	1.05290	0.17330	0.0490*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0449 (6)	0.0267 (5)	0.0335 (5)	0.0108 (4)	0.0049 (4)	0.0052 (4)
N2	0.0647 (8)	0.0351 (5)	0.0295 (5)	0.0189 (5)	0.0043 (5)	0.0073 (4)
N3	0.0455 (6)	0.0304 (5)	0.0317 (5)	0.0143 (4)	0.0054 (4)	0.0069 (4)
N4	0.0604 (7)	0.0388 (6)	0.0365 (6)	0.0232 (5)	0.0056 (5)	0.0116 (4)
N5	0.0497 (6)	0.0356 (5)	0.0315 (5)	0.0139 (5)	0.0041 (4)	0.0055 (4)
C2	0.0395 (6)	0.0286 (5)	0.0317 (5)	0.0082 (4)	0.0061 (5)	0.0059 (4)
C4	0.0406 (6)	0.0317 (5)	0.0333 (6)	0.0115 (5)	0.0063 (5)	0.0083 (4)
C6	0.0425 (6)	0.0318 (6)	0.0338 (6)	0.0075 (5)	0.0054 (5)	0.0037 (4)
C7	0.0673 (10)	0.0378 (7)	0.0401 (7)	0.0135 (7)	0.0076 (7)	−0.0031 (5)
O1	0.0796 (8)	0.0429 (5)	0.0323 (5)	0.0219 (5)	0.0055 (5)	0.0100 (4)
O2	0.0847 (8)	0.0349 (5)	0.0366 (5)	0.0279 (5)	0.0055 (5)	0.0051 (4)
O3	0.1107 (11)	0.0448 (6)	0.0297 (5)	0.0351 (6)	0.0051 (6)	0.0037 (4)
O4	0.0817 (8)	0.0488 (6)	0.0367 (5)	0.0225 (6)	0.0006 (5)	0.0136 (4)
C8	0.0466 (7)	0.0310 (6)	0.0340 (6)	0.0097 (5)	0.0073 (5)	0.0079 (4)
C9	0.0613 (8)	0.0281 (5)	0.0315 (6)	0.0110 (5)	0.0090 (6)	0.0046 (4)
C10	0.0589 (8)	0.0286 (5)	0.0355 (6)	0.0156 (5)	0.0117 (6)	0.0082 (4)
C11	0.0572 (8)	0.0354 (6)	0.0318 (6)	0.0126 (6)	0.0087 (5)	0.0098 (5)

Geometric parameters (Å, º)

O1—C8	1.2371 (16)	N2—H2B	0.8600
O2—C8	1.2690 (17)	N2—H2A	0.8600
O3—C11	1.2927 (19)	N4—H4B	0.8600
O4—C11	1.2250 (18)	N4—H4A	0.8600
O3—H3	0.8200	C6—C7	1.482 (2)
N1—C6	1.3526 (17)	C7—H7C	0.9600
N1—C2	1.3691 (16)	C7—H7A	0.9600
N2—C2	1.3129 (16)	C7—H7B	0.9600
N3—C2	1.3287 (17)	C8—C9	1.4888 (18)
N3—C4	1.3403 (16)	C9—C10	1.3319 (18)
N4—C4	1.3186 (18)	C10—C11	1.4769 (18)
N5—C6	1.3015 (18)	C9—H9	0.9300
N5—C4	1.3692 (17)	C10—H10	0.9300
N1—H1	0.8600
O1···C2^i	3.3425 (19)	C8···C4^vii	3.467 (2)
O1···C9^ii	3.4143 (17)	C8···N4^vii	3.308 (2)
O1···N1	2.7423 (15)	C8···O3	3.1182 (16)
O2···C6^i	3.321 (2)	C9···N4^vii	3.447 (2)
O2···N2	2.7852 (16)	C9···O1^ii	3.4143 (17)
O2···C11	3.0752 (18)	C9···C4^i	3.423 (2)
O2···O3	2.4375 (15)	C10···C11^iv	3.556 (2)
O3···N2^iii	3.0650 (15)	C10···O4^iv	3.246 (2)
O3···O2	2.4375 (15)	C10···C4^i	3.592 (2)
O3···C8	3.1182 (16)	C11···N2^iii	3.4184 (17)
O4···C10^iv	3.246 (2)	C11···C10^iv	3.556 (2)
O4···N4^v	2.8346 (17)	C11···C11^iv	3.545 (2)
O4···N2^iii	2.9406 (16)	C11···O2	3.0752 (18)
O1···H1	1.8800	C8···H3	2.4000
O1···H9^ii	2.5800	C8···H2B	2.7900
O2···H7B^i	2.8400	C8···H1	2.7000
O2···H1	2.9000	C9···H9^ii	2.9300
O2···H3	1.6200	C9···H3	2.6100
O2···H2B	1.9300	C11···H2A^iii	2.6900
O3···H2B^iii	2.8900	H1···H7B	2.5900
O3···H2A^iii	2.5900	H1···H7C	2.5400
O4···H7C^vi	2.8100	H1···H2B	2.2900
O4···H2A^iii	2.0900	H1···O1	1.8800
O4···H4B^v	2.1900	H1···O2	2.9000
O4···H4A^v	2.8900	H1···C8	2.7000
N1···O1	2.7423 (15)	H2A···O3^iii	2.5900
N1···C2^vii	3.3968 (17)	H2A···O4^iii	2.0900
N2···O2	2.7852 (16)	H2A···C11^iii	2.6900
N2···C11^iii	3.4184 (17)	H2B···O2	1.9300
N2···C6^vii	3.4089 (19)	H2B···O3^iii	2.8900
N2···O4^iii	2.9406 (16)	H2B···C8	2.7900
N2···O3^iii	3.0650 (15)	H2B···H1	2.2900
N3···N4^viii	3.0660 (17)	H3···O2	1.6200
N4···O4^ix	2.8346 (17)	H3···C9	2.6100
N4···C9^vii	3.447 (2)	H3···C8	2.4000
N4···N3^viii	3.0660 (17)	H4A···N3^viii	2.2100
N4···C8^vii	3.308 (2)	H4A···O4^ix	2.8900
N3···H4A^viii	2.2100	H4B···O4^ix	2.1900
N5···H7A^x	2.8700	H7A···H7A^x	2.5800
C2···N1^vii	3.3968 (17)	H7A···N5^x	2.8700
C2···O1^i	3.3425 (19)	H7B···H1	2.5900
C4···C8^vii	3.467 (2)	H7B···O2^i	2.8400
C4···C10^i	3.592 (2)	H7C···H1	2.5400
C4···C9^i	3.423 (2)	H7C···O4^xi	2.8100
C6···O2^i	3.321 (2)	H9···O1^ii	2.5800
C6···C8^i	3.425 (2)	H9···C9^ii	2.9300
C6···N2^vii	3.4089 (19)	H9···H9^ii	2.2600
C8···C6^i	3.425 (2)
C11—O3—H3	109.00	N1—C6—C7	116.83 (12)
C2—N1—C6	119.39 (11)	C6—C7—H7B	109.00
C2—N3—C4	115.87 (11)	C6—C7—H7C	109.00
C4—N5—C6	115.48 (11)	H7A—C7—H7B	109.00
C2—N1—H1	120.00	H7A—C7—H7C	109.00
C6—N1—H1	120.00	H7B—C7—H7C	109.00
C2—N2—H2A	120.00	C6—C7—H7A	109.00
C2—N2—H2B	120.00	O1—C8—O2	123.24 (13)
H2A—N2—H2B	120.00	O2—C8—C9	119.39 (12)
H4A—N4—H4B	120.00	O1—C8—C9	117.37 (12)
C4—N4—H4A	120.00	C8—C9—C10	129.89 (12)
C4—N4—H4B	120.00	C9—C10—C11	131.29 (12)
N2—C2—N3	120.60 (11)	O3—C11—C10	120.92 (12)
N1—C2—N2	118.47 (11)	O4—C11—C10	118.76 (13)
N1—C2—N3	120.94 (11)	O3—C11—O4	120.28 (12)
N3—C4—N5	125.89 (12)	C8—C9—H9	115.00
N4—C4—N5	116.65 (12)	C10—C9—H9	115.00
N3—C4—N4	117.46 (12)	C9—C10—H10	114.00
N5—C6—C7	120.74 (12)	C11—C10—H10	114.00
N1—C6—N5	122.43 (12)
C6—N1—C2—N2	179.56 (13)	C6—N5—C4—N3	−1.2 (2)
C6—N1—C2—N3	−1.05 (19)	C4—N5—C6—N1	0.5 (2)
C2—N1—C6—C7	−179.33 (14)	C4—N5—C6—C7	−179.63 (14)
C2—N1—C6—N5	0.6 (2)	O1—C8—C9—C10	−170.33 (16)
C4—N3—C2—N2	179.79 (13)	O2—C8—C9—C10	9.2 (2)
C2—N3—C4—N4	−179.47 (13)	C8—C9—C10—C11	−1.8 (3)
C4—N3—C2—N1	0.41 (19)	C9—C10—C11—O3	−8.3 (3)
C2—N3—C4—N5	0.7 (2)	C9—C10—C11—O4	174.06 (16)
C6—N5—C4—N4	179.02 (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) x−1, y+1, z−1; (vi) x−1, y, z−1; (vii) −x+1, −y+1, −z+1; (viii) −x+1, −y, −z+1; (ix) x+1, y−1, z+1; (x) −x+1, −y+1, −z+2; (xi) x+1, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1	0.86	1.88	2.7423 (15)	179
N2—H2A···O3^iii	0.86	2.59	3.0650 (15)	116
N2—H2A···O4^iii	0.86	2.09	2.9406 (16)	169
N2—H2B···O2	0.86	1.93	2.7852 (16)	177
O3—H3···O2	0.82	1.62	2.4375 (15)	176
N4—H4A···N3^viii	0.86	2.21	3.0660 (17)	173
N4—H4B···O4^ix	0.86	2.19	2.8346 (17)	132
C9—H9···O1^ii	0.93	2.58	3.4143 (17)	150

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

(III) 2,4-diamino-6-methyl-1,3,5-triazinium 3-hydroxypicolinate monohydrate

Crystal data

C4H8N5^+·C6H4NO3^−·H2O	F(000) = 592
Mr = 282.27	Dx = 1.442 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3233 reflections
a = 7.0397 (16) Å	θ = 2.8–28.4°
b = 24.680 (5) Å	µ = 0.11 mm^−1
c = 7.5047 (19) Å	T = 296 K
β = 94.462 (7)°	Chunk, colourless
V = 1299.9 (5) Å^3	0.56 × 0.42 × 0.28 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	3233 independent reflections
Radiation source: fine-focus sealed tube	2090 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 28.4°, θmin = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.939, Tmax = 0.969	k = −32→19
10842 measured reflections	l = −10→9

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.154	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0729P)^2 + 0.252P] where P = (Fo^2 + 2Fc^2)/3
3233 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.24 e Å^−3
3 restraints	Δρmin = −0.19 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
N1	0.4970 (2)	0.54462 (5)	0.29495 (19)	0.0396 (4)
N2	0.7324 (2)	0.48069 (6)	0.3382 (2)	0.0488 (5)
N3	0.4543 (2)	0.45687 (5)	0.1802 (2)	0.0412 (5)
N4	0.1705 (2)	0.43923 (6)	0.0267 (2)	0.0495 (5)
N5	0.2094 (2)	0.52480 (6)	0.1388 (2)	0.0417 (5)
C2	0.5628 (2)	0.49280 (6)	0.2702 (2)	0.0381 (5)
C4	0.2825 (2)	0.47337 (6)	0.1182 (2)	0.0392 (5)
C6	0.3210 (2)	0.55867 (7)	0.2275 (2)	0.0396 (5)
C7	0.2589 (3)	0.61504 (7)	0.2581 (3)	0.0514 (6)
O1	0.9117 (2)	0.56798 (5)	0.5168 (2)	0.0673 (5)
O2	0.6960 (2)	0.63282 (6)	0.4812 (2)	0.0587 (5)
O3	0.7440 (2)	0.72142 (6)	0.6472 (2)	0.0698 (6)
N6	1.1557 (2)	0.63392 (6)	0.7091 (2)	0.0506 (5)
C8	0.9812 (3)	0.65177 (6)	0.6571 (2)	0.0407 (5)
C9	0.9204 (3)	0.70349 (7)	0.7004 (3)	0.0492 (6)
C10	1.0479 (4)	0.73694 (8)	0.7986 (3)	0.0654 (8)
C11	1.2240 (4)	0.71853 (9)	0.8486 (3)	0.0693 (9)
C12	1.2752 (3)	0.66644 (9)	0.8022 (3)	0.0608 (7)
C13	0.8553 (3)	0.61401 (7)	0.5446 (3)	0.0462 (6)
O1W	0.7024 (3)	0.66313 (6)	0.1112 (3)	0.0789 (8)
H1	0.56820	0.56790	0.35330	0.0470*
H2A	0.77690	0.44860	0.32530	0.0590*
H2B	0.80050	0.50470	0.39630	0.0590*
H4A	0.20900	0.40680	0.00790	0.0590*
H4B	0.05870	0.44930	−0.01460	0.0590*
H7A	0.12930	0.61950	0.21050	0.0770*
H7B	0.33910	0.63970	0.19950	0.0770*
H7C	0.26800	0.62240	0.38400	0.0770*
H3	0.68810	0.69840	0.58400	0.1050*
H10	1.01200	0.77170	0.82970	0.0780*
H11	1.31090	0.74060	0.91390	0.0830*
H12	1.39700	0.65400	0.83760	0.0730*
H1W	0.710 (4)	0.6949 (7)	0.095 (4)	0.097 (10)*
H2W	0.714 (5)	0.6586 (13)	0.220 (3)	0.136 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0392 (8)	0.0302 (7)	0.0483 (8)	−0.0028 (6)	−0.0028 (6)	−0.0039 (6)
N2	0.0472 (9)	0.0336 (7)	0.0630 (10)	0.0021 (6)	−0.0121 (8)	−0.0024 (6)
N3	0.0422 (8)	0.0290 (7)	0.0515 (9)	−0.0013 (6)	−0.0029 (7)	0.0003 (6)
N4	0.0430 (9)	0.0343 (7)	0.0695 (11)	−0.0032 (6)	−0.0069 (8)	−0.0071 (7)
N5	0.0360 (8)	0.0342 (7)	0.0544 (9)	−0.0001 (6)	0.0002 (7)	−0.0029 (6)
C2	0.0425 (9)	0.0296 (8)	0.0417 (9)	−0.0015 (7)	−0.0002 (7)	0.0035 (6)
C4	0.0397 (9)	0.0322 (8)	0.0456 (9)	−0.0037 (7)	0.0032 (8)	0.0015 (7)
C6	0.0389 (9)	0.0337 (8)	0.0462 (10)	−0.0029 (7)	0.0038 (8)	0.0000 (7)
C7	0.0486 (11)	0.0373 (9)	0.0680 (13)	0.0031 (8)	0.0019 (9)	−0.0076 (8)
O1	0.0675 (10)	0.0387 (7)	0.0919 (11)	0.0034 (7)	−0.0184 (8)	−0.0219 (7)
O2	0.0516 (8)	0.0495 (8)	0.0720 (10)	0.0006 (6)	−0.0136 (7)	−0.0033 (7)
O3	0.0686 (10)	0.0400 (8)	0.0990 (13)	0.0121 (7)	−0.0052 (9)	−0.0107 (7)
N6	0.0543 (10)	0.0410 (8)	0.0541 (9)	0.0004 (7)	−0.0109 (8)	−0.0045 (7)
C8	0.0501 (10)	0.0308 (8)	0.0406 (9)	−0.0014 (7)	−0.0010 (8)	0.0004 (7)
C9	0.0611 (12)	0.0350 (9)	0.0513 (11)	0.0018 (8)	0.0028 (9)	−0.0011 (8)
C10	0.0912 (18)	0.0379 (10)	0.0657 (14)	−0.0029 (11)	−0.0027 (12)	−0.0131 (9)
C11	0.0868 (18)	0.0515 (12)	0.0656 (14)	−0.0159 (12)	−0.0187 (13)	−0.0116 (10)
C12	0.0620 (13)	0.0555 (12)	0.0618 (13)	−0.0048 (10)	−0.0154 (11)	−0.0058 (10)
C13	0.0496 (11)	0.0374 (9)	0.0507 (11)	−0.0031 (8)	−0.0026 (8)	−0.0001 (8)
O1W	0.1168 (16)	0.0356 (8)	0.0838 (14)	−0.0087 (9)	0.0039 (11)	−0.0032 (8)

Geometric parameters (Å, º)

O1—C13	1.227 (2)	N4—H4A	0.8600
O2—C13	1.271 (3)	N4—H4B	0.8600
O3—C9	1.349 (3)	N6—C12	1.322 (3)
O3—H3	0.8200	N6—C8	1.335 (2)
O1W—H1W	0.796 (18)	C6—C7	1.482 (2)
O1W—H2W	0.82 (2)	C7—H7B	0.9600
N1—C2	1.378 (2)	C7—H7A	0.9600
N1—C6	1.347 (2)	C7—H7C	0.9600
N2—C2	1.296 (2)	C8—C13	1.500 (3)
N3—C4	1.326 (2)	C8—C9	1.393 (2)
N3—C2	1.321 (2)	C9—C10	1.388 (3)
N4—C4	1.311 (2)	C10—C11	1.346 (4)
N5—C6	1.295 (2)	C11—C12	1.387 (3)
N5—C4	1.383 (2)	C10—H10	0.9300
N1—H1	0.8600	C11—H11	0.9300
N2—H2A	0.8600	C12—H12	0.9300
N2—H2B	0.8600
O1···N6	2.701 (2)	C10···C9^v	3.533 (3)
O1···N2^i	2.912 (2)	C13···C4^ii	3.518 (3)
O1···C4^ii	3.316 (2)	C6···H4B^vii	3.0100
O1···N2	2.787 (2)	C8···H2A^i	3.0000
O1W···O3^iii	2.875 (2)	C8···H7C^viii	3.0700
O1W···O2	2.880 (3)	C9···H10^iii	2.9700
O1W···N4^iv	2.898 (2)	C9···H1W^v	2.99 (2)
O2···O1W	2.880 (3)	C12···H7B^ix	3.0500
O2···O3	2.526 (2)	C12···H2A^i	3.0100
O2···N1	2.890 (2)	C13···H1	2.6400
O2···C7	3.415 (3)	C13···H2W	2.79 (3)
O3···O1W^v	2.875 (2)	C13···H3	2.4200
O3···O2	2.526 (2)	C13···H2B	2.9300
O1···H2B^i	2.7500	H1···H7C	2.5300
O1···H2A^i	2.4400	H1···O1	2.6300
O1···H2B	1.9400	H1···H2B	2.2600
O1···H1	2.6300	H1···O2	2.0400
O1W···H4A^iv	2.0600	H1···C13	2.6400
O1W···H7B	2.7500	H1W···C9^iii	2.99 (2)
O1W···H12^vi	2.8600	H1W···O3^iii	2.112 (18)
O2···H3	1.8000	H2A···C12^i	3.0100
O2···H1	2.0400	H2A···O1^i	2.4400
O2···H2W	2.07 (2)	H2A···N6^i	2.1100
O3···H1W^v	2.112 (18)	H2A···C8^i	3.0000
N1···C2^ii	3.449 (2)	H2B···O1^i	2.7500
N1···O2	2.890 (2)	H2B···O1	1.9400
N2···O1	2.787 (2)	H2B···H1	2.2600
N2···C6^ii	3.449 (2)	H2B···C13	2.9300
N2···O1^i	2.912 (2)	H2W···C13	2.79 (3)
N2···N6^i	2.965 (2)	H2W···O2	2.07 (2)
N4···O1W^iv	2.898 (2)	H2W···H4A^iv	2.4400
N4···N5^vii	2.994 (2)	H3···C13	2.4200
N5···N4^vii	2.994 (2)	H3···O2	1.8000
N6···N2^i	2.965 (2)	H4A···H2W^iv	2.4400
N6···O1	2.701 (2)	H4A···O1W^iv	2.0600
N3···H12^i	2.9400	H4B···H7A^vii	2.5500
N5···H4B^vii	2.1400	H4B···N5^vii	2.1400
N6···H7C^viii	2.6400	H4B···C6^vii	3.0100
N6···H2A^i	2.1100	H7A···H4B^vii	2.5500
C2···N1^ii	3.449 (2)	H7B···C12^vi	3.0500
C2···C4^iv	3.298 (2)	H7B···O1W	2.7500
C4···O1^ii	3.316 (2)	H7C···H1	2.5300
C4···C2^iv	3.298 (2)	H7C···C8^x	3.0700
C4···C13^ii	3.518 (3)	H7C···N6^x	2.6400
C6···N2^ii	3.449 (2)	H10···C9^v	2.9700
C7···O2	3.415 (3)	H12···O1W^ix	2.8600
C9···C10^iii	3.533 (3)	H12···N3^i	2.9400
C9—O3—H3	109.00	C6—C7—H7B	109.00
H1W—O1W—H2W	106 (3)	C6—C7—H7C	109.00
C2—N1—C6	119.83 (14)	H7A—C7—H7B	109.00
C2—N3—C4	116.65 (13)	H7B—C7—H7C	110.00
C4—N5—C6	115.70 (14)	H7A—C7—H7C	109.00
C6—N1—H1	120.00	N6—C8—C9	121.80 (17)
C2—N1—H1	120.00	N6—C8—C13	116.72 (15)
C2—N2—H2A	120.00	C9—C8—C13	121.46 (18)
C2—N2—H2B	120.00	O3—C9—C8	121.61 (18)
H2A—N2—H2B	120.00	C8—C9—C10	118.1 (2)
H4A—N4—H4B	120.00	O3—C9—C10	120.28 (18)
C4—N4—H4B	120.00	C9—C10—C11	119.4 (2)
C4—N4—H4A	120.00	C10—C11—C12	119.7 (2)
C8—N6—C12	119.17 (16)	N6—C12—C11	121.9 (2)
N1—C2—N3	120.32 (13)	O2—C13—C8	116.69 (16)
N2—C2—N3	121.64 (14)	O1—C13—O2	124.21 (19)
N1—C2—N2	118.03 (14)	O1—C13—C8	119.09 (18)
N3—C4—N4	118.78 (14)	C11—C10—H10	120.00
N3—C4—N5	125.45 (14)	C9—C10—H10	120.00
N4—C4—N5	115.76 (14)	C10—C11—H11	120.00
N5—C6—C7	120.74 (15)	C12—C11—H11	120.00
N1—C6—C7	117.22 (15)	N6—C12—H12	119.00
N1—C6—N5	122.04 (15)	C11—C12—H12	119.00
C6—C7—H7A	109.00
C6—N1—C2—N2	−179.51 (15)	C8—N6—C12—C11	0.5 (3)
C6—N1—C2—N3	0.2 (2)	N6—C8—C9—O3	179.85 (17)
C2—N1—C6—N5	0.0 (2)	N6—C8—C9—C10	0.8 (3)
C2—N1—C6—C7	−179.78 (15)	C13—C8—C9—O3	1.8 (3)
C4—N3—C2—N1	−0.5 (2)	C13—C8—C9—C10	−177.28 (19)
C4—N3—C2—N2	179.24 (15)	N6—C8—C13—O1	5.2 (3)
C2—N3—C4—N4	179.40 (15)	N6—C8—C13—O2	−173.62 (17)
C2—N3—C4—N5	0.6 (2)	C9—C8—C13—O1	−176.69 (19)
C6—N5—C4—N3	−0.4 (2)	C9—C8—C13—O2	4.5 (3)
C6—N5—C4—N4	−179.25 (14)	O3—C9—C10—C11	−179.2 (2)
C4—N5—C6—N1	0.1 (2)	C8—C9—C10—C11	−0.1 (3)
C4—N5—C6—C7	179.86 (15)	C9—C10—C11—C12	−0.3 (3)
C12—N6—C8—C9	−0.9 (3)	C10—C11—C12—N6	0.2 (3)
C12—N6—C8—C13	177.21 (18)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.86	2.04	2.890 (2)	169
O1W—H1W···O3^iii	0.796 (18)	2.112 (18)	2.875 (2)	161 (3)
N2—H2A···O1^i	0.86	2.44	2.912 (2)	115
N2—H2A···N6^i	0.86	2.11	2.965 (2)	172
N2—H2B···O1	0.86	1.94	2.787 (2)	169
O1W—H2W···O2	0.82 (2)	2.07 (2)	2.880 (3)	166 (3)
O3—H3···O2	0.82	1.80	2.526 (2)	147
N4—H4A···O1W^iv	0.86	2.06	2.898 (2)	164
N4—H4B···N5^vii	0.86	2.14	2.994 (2)	175

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