Melaminium nitrate-melamine-water (1/1/1).

In the crystal structure of the title salt, C(3)H(7)N(6) (+)·NO(3) (-)·C(3)H(6)N(6)·H(2)O, the asymmetric unit consists of two neutral melamine (1,3,5-triazine-2,4,6-triamine) mol-ecules, two melaminium cations, two nitrate anions and two solvent water mol-ecules. One of the nitrate anions is disordered over two sets of positions, with a refined occupancy ratio of 0.909 (3):0.091 (3). The cations and neutral mol-ecules are approximately planar, with maximum deviations of 0.018 (2), 0.024 (2), 0.019 (2) and 0.007 (2) Å for each, respectively. In the crystal structure, melaminium cations and netural melamine mol-ecules self-assemble via N-H⋯N hydrogen bonds to form a supra-molecular hexa-gonal-shaped motif. In addition, the nitrate anions and water mol-ecules are connected by N-H⋯O hydrogen bonds to form a three-dimensional network.

Related literature

For applications of melamine, see: Rima et al. (2008 ▶); Cook et al. (2005 ▶); Ramos Silva et al. (2008 ▶). For related structures, see: Debrus et al. (2007 ▶); Zhao & Shi (2010 ▶); Marchewka & Pietraszko (2003 ▶); Marchewka (2002 ▶). For applications of hydrogen bonding, see: Aghabozorg et al. (2008 ▶).

Experimental

Crystal data

C3H7N6 +·NO3 −·C3H6N6·H2O

M = 333.31

Triclinic,

a = 7.7759 (1) Å

b = 9.0035 (1) Å

c = 19.4573 (3) Å

α = 96.182 (1)°

β = 90.854 (1)°

γ = 99.828 (1)°

V = 1333.64 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.14 mm−1

T = 296 K

0.21 × 0.14 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.972, T max = 0.987

22196 measured reflections

5160 independent reflections

3689 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.123

S = 1.03

5160 reflections

543 parameters

All H-atom parameters refined

Δρmax = 0.21 e Å−3

Δρmin = −0.45 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043941/lh5157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043941/lh5157Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C3H7N6+·NO3−·C3H6N6·H2O	Z = 4
Mr = 333.31	F(000) = 696
Triclinic, P1	Dx = 1.660 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7759 (1) Å	Cell parameters from 3833 reflections
b = 9.0035 (1) Å	θ = 2.3–29.8°
c = 19.4573 (3) Å	µ = 0.14 mm−1
α = 96.182 (1)°	T = 296 K
β = 90.854 (1)°	Block, purple
γ = 99.828 (1)°	0.21 × 0.14 × 0.09 mm
V = 1333.64 (3) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5160 independent reflections
Radiation source: fine-focus sealed tube	3689 reflections with I > 2σ(I)
graphite	Rint = 0.042
φ and ω scans	θmax = 26.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −8→9
Tmin = 0.972, Tmax = 0.987	k = −11→11
22196 measured reflections	l = −23→23

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.0625P)2 + 0.2158P] where P = (Fo2 + 2Fc2)/3
5160 reflections	(Δ/σ)max < 0.001
543 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq	Occ. (<1)
N1A	0.9356 (2)	0.62933 (18)	−0.08016 (9)	0.0142 (4)
N2A	0.7288 (2)	0.48794 (18)	−0.01488 (8)	0.0149 (4)
N3A	0.9137 (2)	0.71794 (18)	0.03718 (8)	0.0139 (4)
N4A	0.7628 (2)	0.4097 (2)	−0.12989 (9)	0.0176 (4)
N5A	0.7043 (2)	0.5825 (2)	0.09767 (9)	0.0172 (4)
N6A	1.1157 (2)	0.8451 (2)	−0.03080 (10)	0.0165 (4)
C1A	0.8069 (2)	0.5077 (2)	−0.07424 (10)	0.0139 (4)
C2A	0.7836 (2)	0.5972 (2)	0.03848 (10)	0.0145 (4)
C3A	0.9888 (2)	0.7321 (2)	−0.02329 (10)	0.0136 (4)
N1B	0.2450 (2)	0.17275 (18)	0.20073 (8)	0.0157 (4)
N2B	0.4686 (2)	0.29201 (18)	0.13081 (8)	0.0149 (4)
N3B	0.2675 (2)	0.07228 (18)	0.08247 (8)	0.0152 (4)
N4B	0.4452 (2)	0.3774 (2)	0.24538 (9)	0.0183 (4)
N5B	0.4750 (2)	0.1976 (2)	0.01677 (9)	0.0160 (4)
N6B	0.0627 (2)	−0.0409 (2)	0.15269 (10)	0.0196 (4)
C1B	0.3839 (2)	0.2789 (2)	0.19097 (10)	0.0148 (4)
C2B	0.4012 (2)	0.1864 (2)	0.07766 (10)	0.0129 (4)
C3B	0.1951 (2)	0.0700 (2)	0.14507 (10)	0.0148 (4)
N1C	0.4424 (2)	1.05878 (19)	0.34890 (9)	0.0170 (4)
N2C	0.4197 (2)	1.15377 (18)	0.46499 (8)	0.0143 (4)
N3C	0.2251 (2)	0.92779 (18)	0.41389 (8)	0.0158 (4)
N4C	0.6243 (2)	1.2761 (2)	0.39577 (10)	0.0182 (4)
N5C	0.2192 (2)	1.0143 (2)	0.52802 (9)	0.0155 (4)
N6C	0.2541 (3)	0.8500 (2)	0.29859 (9)	0.0221 (4)
C1C	0.4950 (2)	1.1634 (2)	0.40435 (10)	0.0149 (4)
C2C	0.2901 (2)	1.0327 (2)	0.46781 (10)	0.0140 (4)
C3C	0.3043 (3)	0.9436 (2)	0.35478 (10)	0.0162 (4)
N1D	0.2208 (2)	0.40060 (18)	0.37041 (8)	0.0155 (4)
N2D	0.2450 (2)	0.48189 (18)	0.49238 (8)	0.0149 (4)
N3D	0.0365 (2)	0.26250 (18)	0.44780 (8)	0.0145 (4)
N4D	0.4156 (2)	0.6117 (2)	0.41573 (10)	0.0180 (4)
N5D	0.0681 (3)	0.3419 (2)	0.56411 (9)	0.0174 (4)
N6D	0.0204 (2)	0.1911 (2)	0.32993 (9)	0.0180 (4)
C1D	0.2918 (2)	0.4954 (2)	0.42667 (10)	0.0139 (4)
C2D	0.1182 (2)	0.3630 (2)	0.49989 (10)	0.0142 (4)
C3D	0.0951 (3)	0.2865 (2)	0.38480 (10)	0.0137 (4)
N8A	0.7624 (2)	0.76433 (19)	0.28672 (9)	0.0178 (4)*
O1AA	0.8234 (2)	0.77664 (18)	0.22811 (8)	0.0211 (4)	0.909 (3)
O2AA	0.7867 (2)	0.87285 (18)	0.33240 (8)	0.0293 (5)	0.909 (3)
O3AA	0.6809 (2)	0.63698 (18)	0.30001 (8)	0.0305 (5)	0.909 (3)
O1AB	0.887 (2)	0.8747 (18)	0.2933 (8)	0.021 (4)*	0.091 (3)
O2AB	0.649 (2)	0.7781 (19)	0.3371 (8)	0.026 (5)*	0.091 (3)
O3AB	0.721 (2)	0.673 (2)	0.2387 (9)	0.029 (5)*	0.091 (3)
N8B	0.5925 (2)	0.96755 (18)	0.17530 (8)	0.0163 (4)
O1B	0.46913 (19)	0.86023 (16)	0.18015 (7)	0.0240 (4)
O2B	0.66849 (18)	0.98031 (16)	0.11995 (7)	0.0200 (3)
O3B	0.64020 (18)	1.06308 (15)	0.22762 (7)	0.0191 (3)
O1W	0.1736 (2)	0.67667 (17)	0.81644 (8)	0.0188 (3)
O2W	0.0718 (2)	0.54790 (17)	0.26433 (8)	0.0217 (4)
H1N	0.997 (3)	0.639 (3)	−0.1192 (12)	0.028 (6)*
H2N	0.504 (3)	1.061 (3)	0.3083 (12)	0.032 (7)*
H1A	0.816 (3)	0.430 (2)	−0.1706 (12)	0.023 (6)*
H2A	0.668 (3)	0.328 (3)	−0.1251 (13)	0.044 (8)*
H3A	0.622 (3)	0.504 (3)	0.1019 (11)	0.022 (6)*
H4A	0.739 (3)	0.648 (3)	0.1329 (11)	0.019 (6)*
H5A	1.154 (3)	0.905 (3)	0.0016 (12)	0.020 (6)*
H6A	1.157 (3)	0.853 (2)	−0.0732 (12)	0.020 (6)*
H1B	0.382 (3)	0.377 (2)	0.2808 (11)	0.018 (6)*
H2B	0.531 (3)	0.460 (3)	0.2400 (11)	0.030 (7)*
H3B	0.543 (3)	0.276 (3)	0.0113 (11)	0.022 (6)*
H4B	0.426 (3)	0.137 (3)	−0.0177 (12)	0.025 (6)*
H5B	0.021 (3)	−0.106 (3)	0.1195 (12)	0.023 (6)*
H6B	0.014 (3)	−0.044 (3)	0.1938 (12)	0.027 (7)*
H1C	0.676 (3)	1.277 (3)	0.3554 (13)	0.030 (7)*
H2C	0.668 (3)	1.346 (3)	0.4295 (13)	0.033 (7)*
H3C	0.259 (3)	1.082 (3)	0.5641 (12)	0.025 (6)*
H4C	0.138 (3)	0.934 (3)	0.5318 (12)	0.032 (7)*
H5C	0.172 (4)	0.762 (3)	0.3000 (13)	0.047 (8)*
H6C	0.318 (3)	0.858 (2)	0.2606 (11)	0.016 (6)*
H1D	0.458 (3)	0.616 (2)	0.3741 (11)	0.014 (6)*
H2D	0.459 (3)	0.669 (3)	0.4510 (12)	0.024 (6)*
H3D	0.129 (3)	0.396 (3)	0.5980 (12)	0.030 (7)*
H4D	−0.005 (3)	0.268 (3)	0.5669 (11)	0.026 (7)*
H5D	−0.051 (3)	0.102 (3)	0.3382 (12)	0.034 (7)*
H6D	0.082 (3)	0.194 (3)	0.2905 (12)	0.027 (6)*
H1W1	0.203 (4)	0.765 (3)	0.7943 (14)	0.054 (9)*
H2W1	0.270 (4)	0.673 (4)	0.8371 (17)	0.084 (12)*
H1W2	0.116 (4)	0.499 (3)	0.2936 (15)	0.055 (9)*
H2W2	−0.034 (4)	0.480 (3)	0.2477 (13)	0.042 (7)*

	U11	U22	U33	U12	U13	U23
N1A	0.0151 (9)	0.0154 (9)	0.0106 (9)	−0.0008 (7)	0.0026 (7)	0.0005 (7)
N2A	0.0170 (9)	0.0132 (9)	0.0134 (9)	0.0003 (7)	0.0005 (7)	0.0004 (7)
N3A	0.0148 (9)	0.0140 (9)	0.0118 (9)	−0.0006 (7)	0.0013 (7)	0.0015 (7)
N4A	0.0202 (10)	0.0178 (10)	0.0128 (9)	−0.0014 (8)	0.0022 (8)	−0.0009 (7)
N5A	0.0201 (10)	0.0155 (10)	0.0130 (9)	−0.0047 (8)	0.0032 (8)	−0.0005 (8)
N6A	0.0190 (10)	0.0168 (9)	0.0104 (10)	−0.0043 (7)	0.0027 (8)	−0.0021 (8)
C1A	0.0125 (10)	0.0135 (10)	0.0155 (11)	0.0017 (8)	−0.0004 (8)	0.0017 (8)
C2A	0.0137 (10)	0.0131 (10)	0.0171 (11)	0.0023 (8)	−0.0003 (8)	0.0038 (8)
C3A	0.0133 (10)	0.0128 (10)	0.0153 (10)	0.0038 (8)	−0.0014 (8)	0.0016 (8)
N1B	0.0150 (9)	0.0172 (9)	0.0137 (9)	−0.0002 (7)	0.0011 (7)	0.0006 (7)
N2B	0.0151 (9)	0.0156 (9)	0.0130 (9)	0.0005 (7)	0.0013 (7)	0.0007 (7)
N3B	0.0151 (9)	0.0157 (9)	0.0134 (9)	−0.0007 (7)	−0.0004 (7)	0.0010 (7)
N4B	0.0180 (9)	0.0215 (10)	0.0116 (9)	−0.0046 (8)	0.0049 (8)	−0.0027 (8)
N5B	0.0172 (9)	0.0156 (10)	0.0122 (9)	−0.0041 (8)	0.0016 (7)	−0.0003 (8)
N6B	0.0201 (10)	0.0228 (10)	0.0118 (10)	−0.0067 (8)	0.0027 (8)	−0.0011 (8)
C1B	0.0126 (10)	0.0156 (10)	0.0157 (11)	0.0005 (8)	0.0004 (8)	0.0030 (8)
C2B	0.0124 (10)	0.0135 (10)	0.0133 (10)	0.0031 (8)	−0.0012 (8)	0.0024 (8)
C3B	0.0131 (10)	0.0173 (11)	0.0139 (10)	0.0011 (8)	0.0001 (8)	0.0029 (8)
N1C	0.0196 (9)	0.0160 (9)	0.0131 (9)	−0.0026 (7)	0.0029 (7)	−0.0004 (7)
N2C	0.0149 (9)	0.0149 (9)	0.0127 (9)	0.0015 (7)	0.0021 (7)	0.0009 (7)
N3C	0.0189 (9)	0.0136 (9)	0.0134 (9)	−0.0011 (7)	0.0013 (7)	0.0012 (7)
N4C	0.0205 (10)	0.0179 (10)	0.0131 (10)	−0.0037 (8)	0.0036 (8)	−0.0008 (8)
N5C	0.0179 (9)	0.0137 (9)	0.0129 (9)	−0.0021 (8)	0.0019 (7)	−0.0008 (7)
N6C	0.0271 (11)	0.0206 (10)	0.0142 (10)	−0.0064 (8)	0.0055 (8)	−0.0020 (8)
C1C	0.0142 (10)	0.0145 (10)	0.0163 (11)	0.0037 (8)	−0.0006 (8)	0.0014 (8)
C2C	0.0144 (10)	0.0127 (10)	0.0152 (10)	0.0028 (8)	0.0001 (8)	0.0021 (8)
C3C	0.0169 (10)	0.0137 (10)	0.0172 (11)	0.0010 (8)	0.0011 (8)	0.0016 (8)
N1D	0.0168 (9)	0.0140 (9)	0.0139 (9)	−0.0012 (7)	0.0007 (7)	0.0001 (7)
N2D	0.0164 (9)	0.0150 (9)	0.0130 (9)	0.0019 (7)	0.0010 (7)	0.0015 (7)
N3D	0.0162 (9)	0.0142 (9)	0.0119 (9)	0.0000 (7)	0.0005 (7)	0.0004 (7)
N4D	0.0228 (10)	0.0174 (10)	0.0106 (10)	−0.0044 (8)	0.0022 (8)	−0.0007 (8)
N5D	0.0221 (10)	0.0152 (10)	0.0118 (9)	−0.0045 (8)	0.0014 (8)	−0.0005 (8)
N6D	0.0211 (10)	0.0182 (10)	0.0118 (9)	−0.0040 (8)	0.0023 (8)	−0.0003 (7)
C1D	0.0145 (10)	0.0132 (10)	0.0151 (10)	0.0059 (8)	0.0003 (8)	0.0009 (8)
C2D	0.0151 (10)	0.0147 (10)	0.0137 (10)	0.0037 (8)	0.0015 (8)	0.0037 (8)
C3D	0.0152 (10)	0.0143 (10)	0.0123 (10)	0.0040 (8)	0.0005 (8)	0.0029 (8)
O1AA	0.0246 (9)	0.0249 (10)	0.0128 (8)	0.0000 (7)	0.0057 (7)	0.0038 (7)
O2AA	0.0517 (13)	0.0175 (9)	0.0141 (9)	−0.0037 (8)	0.0020 (8)	−0.0033 (7)
O3AA	0.0362 (11)	0.0232 (10)	0.0240 (10)	−0.0163 (8)	0.0075 (8)	0.0003 (7)
N8B	0.0170 (9)	0.0162 (9)	0.0150 (9)	0.0011 (7)	0.0005 (7)	0.0020 (7)
O1B	0.0221 (8)	0.0201 (8)	0.0247 (8)	−0.0096 (6)	0.0060 (7)	−0.0002 (6)
O2B	0.0226 (8)	0.0227 (8)	0.0130 (7)	−0.0007 (6)	0.0058 (6)	0.0013 (6)
O3B	0.0232 (8)	0.0179 (8)	0.0132 (7)	−0.0020 (6)	0.0019 (6)	−0.0028 (6)
O1W	0.0165 (8)	0.0196 (8)	0.0191 (8)	−0.0011 (6)	0.0027 (7)	0.0031 (6)
O2W	0.0239 (9)	0.0194 (8)	0.0204 (8)	−0.0015 (7)	−0.0047 (7)	0.0048 (7)

N1A—C1A	1.368 (2)	N4C—C1C	1.327 (3)
N1A—C3A	1.374 (2)	N4C—H1C	0.89 (2)
N1A—H1N	0.91 (2)	N4C—H2C	0.88 (2)
N2A—C1A	1.328 (2)	N5C—C2C	1.317 (2)
N2A—C2A	1.361 (2)	N5C—H3C	0.90 (2)
N3A—C3A	1.330 (2)	N5C—H4C	0.89 (3)
N3A—C2A	1.355 (2)	N6C—C3C	1.317 (3)
N4A—C1A	1.322 (2)	N6C—H5C	0.93 (3)
N4A—H1A	0.92 (2)	N6C—H6C	0.90 (2)
N4A—H2A	0.96 (3)	N1D—C3D	1.348 (2)
N5A—C2A	1.323 (3)	N1D—C1D	1.361 (2)
N5A—H3A	0.88 (2)	N2D—C1D	1.347 (2)
N5A—H4A	0.86 (2)	N2D—C2D	1.348 (2)
N6A—C3A	1.313 (2)	N3D—C3D	1.341 (2)
N6A—H5A	0.80 (2)	N3D—C2D	1.356 (2)
N6A—H6A	0.89 (2)	N4D—C1D	1.333 (3)
N1B—C1B	1.345 (2)	N4D—H1D	0.88 (2)
N1B—C3B	1.352 (2)	N4D—H2D	0.84 (2)
N2B—C1B	1.358 (2)	N5D—C2D	1.338 (3)
N2B—C2B	1.360 (2)	N5D—H3D	0.86 (2)
N3B—C2B	1.343 (2)	N5D—H4D	0.81 (2)
N3B—C3B	1.350 (2)	N6D—C3D	1.352 (2)
N4B—C1B	1.332 (2)	N6D—H5D	0.93 (2)
N4B—H1B	0.85 (2)	N6D—H6D	0.91 (2)
N4B—H2B	0.93 (2)	N8A—O3AB	1.180 (17)
N5B—C2B	1.330 (2)	N8A—O2AA	1.235 (2)
N5B—H3B	0.82 (2)	N8A—O1AA	1.250 (2)
N5B—H4B	0.86 (2)	N8A—O1AB	1.257 (16)
N6B—C3B	1.328 (3)	N8A—O3AA	1.266 (2)
N6B—H5B	0.85 (2)	N8A—O2AB	1.340 (16)
N6B—H6B	0.89 (2)	N8B—O2B	1.243 (2)
N1C—C1C	1.362 (2)	N8B—O1B	1.253 (2)
N1C—C3C	1.375 (3)	N8B—O3B	1.267 (2)
N1C—H2N	0.93 (2)	O1W—H1W1	0.94 (3)
N2C—C1C	1.330 (2)	O1W—H2W1	0.85 (4)
N2C—C2C	1.359 (2)	O2W—H1W2	0.86 (3)
N3C—C3C	1.322 (2)	O2W—H2W2	0.96 (3)
N3C—C2C	1.362 (2)
C1A—N1A—C3A	119.68 (17)	H3C—N5C—H4C	123 (2)
C1A—N1A—H1N	122.0 (14)	C3C—N6C—H5C	121.6 (16)
C3A—N1A—H1N	117.9 (14)	C3C—N6C—H6C	119.1 (13)
C1A—N2A—C2A	115.58 (16)	H5C—N6C—H6C	118 (2)
C3A—N3A—C2A	115.82 (16)	N4C—C1C—N2C	120.93 (18)
C1A—N4A—H1A	118.4 (13)	N4C—C1C—N1C	117.64 (18)
C1A—N4A—H2A	116.2 (15)	N2C—C1C—N1C	121.43 (18)
H1A—N4A—H2A	125 (2)	N5C—C2C—N2C	117.48 (17)
C2A—N5A—H3A	120.6 (14)	N5C—C2C—N3C	116.36 (18)
C2A—N5A—H4A	118.9 (14)	N2C—C2C—N3C	126.15 (17)
H3A—N5A—H4A	120 (2)	N6C—C3C—N3C	121.51 (18)
C3A—N6A—H5A	120.8 (16)	N6C—C3C—N1C	116.79 (18)
C3A—N6A—H6A	117.5 (14)	N3C—C3C—N1C	121.70 (17)
H5A—N6A—H6A	122 (2)	C3D—N1D—C1D	114.55 (16)
N4A—C1A—N2A	120.93 (18)	C1D—N2D—C2D	114.67 (16)
N4A—C1A—N1A	117.61 (18)	C3D—N3D—C2D	114.38 (16)
N2A—C1A—N1A	121.47 (17)	C1D—N4D—H1D	119.3 (13)
N5A—C2A—N3A	116.94 (17)	C1D—N4D—H2D	116.6 (15)
N5A—C2A—N2A	116.77 (18)	H1D—N4D—H2D	123 (2)
N3A—C2A—N2A	126.28 (18)	C2D—N5D—H3D	117.8 (15)
N6A—C3A—N3A	121.21 (18)	C2D—N5D—H4D	115.0 (16)
N6A—C3A—N1A	117.70 (18)	H3D—N5D—H4D	126 (2)
N3A—C3A—N1A	121.08 (17)	C3D—N6D—H5D	118.3 (14)
C1B—N1B—C3B	114.54 (16)	C3D—N6D—H6D	115.0 (14)
C1B—N2B—C2B	114.46 (16)	H5D—N6D—H6D	120 (2)
C2B—N3B—C3B	115.23 (16)	N4D—C1D—N2D	117.56 (18)
C1B—N4B—H1B	116.4 (14)	N4D—C1D—N1D	117.41 (18)
C1B—N4B—H2B	120.1 (14)	N2D—C1D—N1D	125.02 (18)
H1B—N4B—H2B	121 (2)	N5D—C2D—N2D	117.53 (18)
C2B—N5B—H3B	118.4 (15)	N5D—C2D—N3D	116.89 (18)
C2B—N5B—H4B	117.1 (15)	N2D—C2D—N3D	125.58 (17)
H3B—N5B—H4B	122 (2)	N3D—C3D—N1D	125.78 (17)
C3B—N6B—H5B	122.0 (15)	N3D—C3D—N6D	118.13 (18)
C3B—N6B—H6B	118.3 (14)	N1D—C3D—N6D	116.07 (17)
H5B—N6B—H6B	120 (2)	O3AB—N8A—O2AA	169.5 (9)
N4B—C1B—N1B	117.02 (18)	O3AB—N8A—O1AA	57.0 (9)
N4B—C1B—N2B	117.46 (17)	O2AA—N8A—O1AA	120.86 (17)
N1B—C1B—N2B	125.51 (17)	O3AB—N8A—O1AB	129.1 (12)
N5B—C2B—N3B	118.21 (17)	O2AA—N8A—O1AB	52.2 (7)
N5B—C2B—N2B	116.93 (17)	O1AA—N8A—O1AB	73.0 (8)
N3B—C2B—N2B	124.86 (17)	O3AB—N8A—O3AA	63.9 (9)
N6B—C3B—N3B	117.65 (18)	O2AA—N8A—O3AA	119.80 (17)
N6B—C3B—N1B	117.06 (18)	O1AA—N8A—O3AA	119.28 (16)
N3B—C3B—N1B	125.28 (17)	O1AB—N8A—O3AA	154.5 (8)
C1C—N1C—C3C	119.51 (17)	O3AB—N8A—O2AB	118.6 (12)
C1C—N1C—H2N	120.2 (15)	O2AA—N8A—O2AB	58.6 (7)
C3C—N1C—H2N	120.2 (14)	O1AA—N8A—O2AB	156.4 (7)
C1C—N2C—C2C	115.68 (16)	O1AB—N8A—O2AB	110.8 (11)
C3C—N3C—C2C	115.38 (17)	O3AA—N8A—O2AB	67.8 (7)
C1C—N4C—H1C	118.9 (15)	O2B—N8B—O1B	120.62 (16)
C1C—N4C—H2C	122.7 (15)	O2B—N8B—O3B	120.05 (16)
H1C—N4C—H2C	118 (2)	O1B—N8B—O3B	119.34 (16)
C2C—N5C—H3C	117.8 (14)	H1W1—O1W—H2W1	102 (3)
C2C—N5C—H4C	119.4 (15)	H1W2—O2W—H2W2	104 (2)
C2A—N2A—C1A—N4A	−179.15 (18)	C2C—N2C—C1C—N4C	−179.32 (18)
C2A—N2A—C1A—N1A	0.9 (3)	C2C—N2C—C1C—N1C	0.9 (3)
C3A—N1A—C1A—N4A	−178.41 (18)	C3C—N1C—C1C—N4C	−177.41 (18)
C3A—N1A—C1A—N2A	1.5 (3)	C3C—N1C—C1C—N2C	2.4 (3)
C3A—N3A—C2A—N5A	−178.58 (18)	C1C—N2C—C2C—N5C	176.16 (18)
C3A—N3A—C2A—N2A	2.8 (3)	C1C—N2C—C2C—N3C	−4.2 (3)
C1A—N2A—C2A—N5A	178.11 (18)	C3C—N3C—C2C—N5C	−176.55 (18)
C1A—N2A—C2A—N3A	−3.2 (3)	C3C—N3C—C2C—N2C	3.8 (3)
C2A—N3A—C3A—N6A	179.66 (19)	C2C—N3C—C3C—N6C	−179.85 (19)
C2A—N3A—C3A—N1A	0.0 (3)	C2C—N3C—C3C—N1C	−0.1 (3)
C1A—N1A—C3A—N6A	178.31 (18)	C1C—N1C—C3C—N6C	176.93 (18)
C1A—N1A—C3A—N3A	−2.0 (3)	C1C—N1C—C3C—N3C	−2.8 (3)
C3B—N1B—C1B—N4B	−176.03 (18)	C2D—N2D—C1D—N4D	179.39 (17)
C3B—N1B—C1B—N2B	2.6 (3)	C2D—N2D—C1D—N1D	0.3 (3)
C2B—N2B—C1B—N4B	178.92 (18)	C3D—N1D—C1D—N4D	−179.25 (17)
C2B—N2B—C1B—N1B	0.3 (3)	C3D—N1D—C1D—N2D	−0.2 (3)
C3B—N3B—C2B—N5B	−178.07 (17)	C1D—N2D—C2D—N5D	178.84 (17)
C3B—N3B—C2B—N2B	2.4 (3)	C1D—N2D—C2D—N3D	−1.2 (3)
C1B—N2B—C2B—N5B	177.45 (17)	C3D—N3D—C2D—N5D	−178.23 (17)
C1B—N2B—C2B—N3B	−3.0 (3)	C3D—N3D—C2D—N2D	1.8 (3)
C2B—N3B—C3B—N6B	−179.74 (18)	C2D—N3D—C3D—N1D	−1.7 (3)
C2B—N3B—C3B—N1B	1.0 (3)	C2D—N3D—C3D—N6D	179.96 (17)
C1B—N1B—C3B—N6B	177.44 (18)	C1D—N1D—C3D—N3D	0.9 (3)
C1B—N1B—C3B—N3B	−3.3 (3)	C1D—N1D—C3D—N6D	179.31 (17)

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H1A···O2Wi	0.92 (2)	2.05 (2)	2.965 (2)	174.2 (17)
N4B—H1B···N1D	0.85 (2)	2.18 (2)	3.025 (2)	174.1 (18)
N4D—H1D···O3AA	0.88 (2)	2.27 (2)	3.077 (2)	153 (2)
N1A—H1N···O1Wii	0.91 (2)	1.89 (2)	2.771 (2)	165 (2)
N4A—H2A···O1Bi	0.96 (3)	2.03 (3)	2.838 (2)	141 (2)
N4B—H2B···O3AA	0.93 (3)	2.05 (2)	2.810 (2)	138.8 (18)
N4C—H2C···N2Diii	0.88 (3)	2.07 (3)	2.945 (2)	176 (2)
N4D—H2D···N2Ciii	0.84 (2)	2.23 (2)	3.069 (2)	172 (2)
N1C—H2N···O3B	0.93 (2)	1.91 (2)	2.836 (2)	177 (2)
O2W—H1W2···N1D	0.86 (3)	2.04 (3)	2.899 (2)	174 (3)
N5A—H3A···N2B	0.88 (3)	2.20 (3)	3.062 (2)	165 (2)
N5B—H3B···N2A	0.82 (3)	2.30 (3)	3.119 (2)	175 (2)
N5C—H3C···O2AAiii	0.89 (2)	2.06 (2)	2.799 (2)	140 (2)
N5D—H3D···O3AAiv	0.86 (2)	2.53 (2)	3.232 (3)	140 (2)
N5A—H4A···O1AA	0.86 (2)	2.11 (2)	2.963 (2)	171 (2)
N5B—H4B···O2Bi	0.86 (2)	2.20 (2)	3.045 (2)	167 (2)
N5C—H4C···N3Dv	0.89 (3)	2.12 (3)	2.996 (2)	173 (2)
N5D—H4D···N3Cv	0.81 (3)	2.30 (3)	3.105 (3)	173 (2)
N6A—H5A···N3Bvi	0.80 (2)	2.13 (2)	2.926 (2)	175.9 (19)
N6B—H5B···N3Avii	0.84 (2)	2.18 (2)	3.020 (2)	177 (2)
N6C—H5C···O2W	0.93 (3)	2.00 (3)	2.849 (2)	151 (2)
N6D—H5D···O2AAvii	0.93 (3)	2.22 (3)	3.126 (2)	167 (2)
N6A—H6A···O1Wii	0.90 (2)	2.55 (2)	3.262 (2)	137.2 (15)
N6A—H6A···O2Bviii	0.90 (2)	2.14 (2)	2.841 (2)	135.2 (17)
N6B—H6B···O1AAvii	0.89 (2)	2.17 (3)	2.806 (2)	128 (2)
N6C—H6C···O1B	0.90 (2)	1.97 (2)	2.868 (2)	174.6 (18)
N6D—H6D···N1B	0.91 (2)	2.18 (2)	3.088 (2)	172 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4A—H1A⋯O2Wi	0.92 (2)	2.05 (2)	2.965 (2)	174.2 (17)
N4B—H1B⋯N1D	0.85 (2)	2.18 (2)	3.025 (2)	174.1 (18)
N4D—H1D⋯O3AA	0.88 (2)	2.27 (2)	3.077 (2)	153 (2)
N1A—H1N⋯O1Wii	0.91 (2)	1.89 (2)	2.771 (2)	165 (2)
N4A—H2A⋯O1Bi	0.96 (3)	2.03 (3)	2.838 (2)	141 (2)
N4B—H2B⋯O3AA	0.93 (3)	2.05 (2)	2.810 (2)	138.8 (18)
N4C—H2C⋯N2Diii	0.88 (3)	2.07 (3)	2.945 (2)	176 (2)
N4D—H2D⋯N2Ciii	0.84 (2)	2.23 (2)	3.069 (2)	172 (2)
N1C—H2N⋯O3B	0.93 (2)	1.91 (2)	2.836 (2)	177 (2)
O2W—H1W2⋯N1D	0.86 (3)	2.04 (3)	2.899 (2)	174 (3)
N5A—H3A⋯N2B	0.88 (3)	2.20 (3)	3.062 (2)	165 (2)
N5B—H3B⋯N2A	0.82 (3)	2.30 (3)	3.119 (2)	175 (2)
N5C—H3C⋯O2AAiii	0.89 (2)	2.06 (2)	2.799 (2)	140 (2)
N5D—H3D⋯O3AAiv	0.86 (2)	2.53 (2)	3.232 (3)	140 (2)
N5A—H4A⋯O1AA	0.86 (2)	2.11 (2)	2.963 (2)	171 (2)
N5B—H4B⋯O2Bi	0.86 (2)	2.20 (2)	3.045 (2)	167 (2)
N5C—H4C⋯N3Dv	0.89 (3)	2.12 (3)	2.996 (2)	173 (2)
N5D—H4D⋯N3Cv	0.81 (3)	2.30 (3)	3.105 (3)	173 (2)
N6A—H5A⋯N3Bvi	0.80 (2)	2.13 (2)	2.926 (2)	175.9 (19)
N6B—H5B⋯N3Avii	0.84 (2)	2.18 (2)	3.020 (2)	177 (2)
N6C—H5C⋯O2W	0.93 (3)	2.00 (3)	2.849 (2)	151 (2)
N6D—H5D⋯O2AAvii	0.93 (3)	2.22 (3)	3.126 (2)	167 (2)
N6A—H6A⋯O1Wii	0.90 (2)	2.55 (2)	3.262 (2)	137.2 (15)
N6A—H6A⋯O2Bviii	0.90 (2)	2.14 (2)	2.841 (2)	135.2 (17)
N6B—H6B⋯O1AAvii	0.89 (2)	2.17 (3)	2.806 (2)	128 (2)
N6C—H6C⋯O1B	0.90 (2)	1.97 (2)	2.868 (2)	174.6 (18)
N6D—H6D⋯N1B	0.91 (2)	2.18 (2)	3.088 (2)	172 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .