Tetra-kis(2,6-diamino-pyridinium) diphthalate 2,6-diamino-pyridine.

In the title compound, 4C(5)H(8)N(3) (+)·2C(8)H(4)O(4) (2-)·C(5)H(7)N(3), the asymmetric unit consists of two protonated diamino-pyridine cations, one phthalate anion and one half of a diamino-pyridine mol-ecule, which has twofold rotation symmetry and is disordered over two positions with a site-occupancy ratio of 0.534 (3):0.466 (3). In the disordered structure, both pyridine rings are essentially planar, with maximum deviations of 0.011 (2) and 0.006 (2) Å, and these two rings are inclined to one another at a dihedral angle of 79.86 (10)°. In the crystal structure, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link the ions and mol-ecules into a three-dimensional network. The structure is further stabilized by C-H⋯π inter-actions.

Related literature

For background to 2,6-diamino­pyridines, see: Abu Zuhri & Cox (1989 ▶); Inuzuka & Fujimoto (1990 ▶). For background and the biological activity of phthalic acid, see: Brike et al. (2002 ▶); Yamamoto et al. (1990 ▶). For the preparation of polymer complexes, see: El-Mossalamy (2001 ▶). For a related structure: see: Büyükgüngör & Odabąsoğlu (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

4C5H8N3 +·2C8H4O4 2−·C5H7N3

M = 877.94

Monoclinic,

a = 29.7011 (6) Å

b = 15.2183 (3) Å

c = 9.7666 (2) Å

β = 101.670 (1)°

V = 4323.25 (15) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.65 × 0.19 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.939, T max = 0.992

28159 measured reflections

6403 independent reflections

3722 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.153

S = 1.05

6403 reflections

368 parameters

138 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.41 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044468/is2475sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044468/is2475Isup2.hkl

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

4C5H8N3+·2C8H4O42−·C5H7N3	F(000) = 1848
Mr = 877.94	Dx = 1.349 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 8039 reflections
a = 29.7011 (6) Å	θ = 2.5–29.2°
b = 15.2183 (3) Å	µ = 0.10 mm−1
c = 9.7666 (2) Å	T = 100 K
β = 101.670 (1)°	Plate, colourless
V = 4323.25 (15) Å3	0.65 × 0.19 × 0.08 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	6403 independent reflections
Radiation source: fine-focus sealed tube	3722 reflections with I > 2σ(I)
graphite	Rint = 0.037
φ and ω scans	θmax = 30.3°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −41→33
Tmin = 0.939, Tmax = 0.992	k = −18→21
28159 measured reflections	l = −13→13

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.153	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0492P)2 + 4.6062P] where P = (Fo2 + 2Fc2)/3
6403 reflections	(Δ/σ)max = 0.001
368 parameters	Δρmax = 0.41 e Å−3
138 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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)
O1	0.21274 (4)	0.08852 (11)	0.21602 (15)	0.0440 (4)
O2	0.22943 (4)	0.23084 (10)	0.25406 (14)	0.0387 (4)
O3	0.13432 (4)	0.19360 (12)	0.30278 (14)	0.0515 (5)
O4	0.06579 (4)	0.23383 (10)	0.18270 (14)	0.0388 (4)
C1	0.18725 (7)	0.19537 (15)	−0.0669 (2)	0.0423 (5)
H1A	0.2177	0.1810	−0.0672	0.051*
C2	0.15801 (8)	0.21910 (16)	−0.1906 (2)	0.0456 (6)
H2A	0.1689	0.2210	−0.2734	0.055*
C3	0.11279 (7)	0.23982 (14)	−0.1911 (2)	0.0405 (5)
H3A	0.0932	0.2558	−0.2742	0.049*
C4	0.09662 (6)	0.23687 (14)	−0.0685 (2)	0.0348 (5)
H4A	0.0660	0.2506	−0.0698	0.042*
C5	0.12550 (6)	0.21362 (13)	0.05745 (18)	0.0300 (4)
C6	0.17151 (6)	0.19283 (14)	0.05818 (18)	0.0325 (5)
C7	0.10699 (6)	0.21365 (14)	0.18992 (19)	0.0342 (5)
C8	0.20650 (6)	0.16996 (16)	0.18790 (19)	0.0347 (5)
N3	0.19685 (7)	0.30697 (15)	0.5108 (2)	0.0480 (5)
N1	0.20894 (5)	0.44706 (13)	0.59887 (17)	0.0355 (4)
N2	0.22822 (6)	0.58214 (16)	0.7028 (2)	0.0431 (5)
C9	0.20034 (6)	0.53472 (15)	0.6039 (2)	0.0369 (5)
C10	0.16395 (7)	0.56915 (17)	0.5066 (2)	0.0475 (6)
H10A	0.1572	0.6289	0.5059	0.057*
C11	0.13800 (7)	0.51321 (17)	0.4111 (2)	0.0497 (6)
H11A	0.1137	0.5363	0.3458	0.060*
C12	0.14655 (7)	0.42488 (17)	0.4086 (2)	0.0447 (6)
H12A	0.1280	0.3884	0.3444	0.054*
C13	0.18370 (6)	0.39106 (16)	0.50433 (19)	0.0384 (5)
N4	0.09366 (6)	0.11944 (16)	0.49015 (18)	0.0464 (5)
N5	0.16327 (6)	0.04646 (18)	0.5394 (2)	0.0502 (6)
N6	0.02842 (7)	0.20371 (18)	0.4271 (2)	0.0634 (7)
C14	0.12044 (6)	0.05699 (17)	0.5647 (2)	0.0448 (6)
C15	0.10308 (7)	0.00880 (16)	0.6624 (2)	0.0455 (6)
H15A	0.1209	−0.0338	0.7163	0.055*
C16	0.05859 (7)	0.02544 (17)	0.6783 (2)	0.0467 (6)
H16A	0.0466	−0.0071	0.7433	0.056*
C17	0.03147 (7)	0.08875 (16)	0.6008 (2)	0.0453 (6)
H17A	0.0016	0.0985	0.6125	0.054*
C18	0.04969 (6)	0.13754 (17)	0.5051 (2)	0.0456 (6)
N7	0.0000	0.5548 (4)	0.7500	0.0334 (16)	0.534 (5)
N8	0.05683 (11)	0.5598 (2)	0.6223 (3)	0.0411 (11)	0.534 (5)
H8A	0.0563	0.6162	0.6294	0.049*	0.534 (5)
H8B	0.0756	0.5352	0.5776	0.049*	0.534 (5)
C19	0.0278 (2)	0.5094 (5)	0.6826 (7)	0.0349 (15)	0.534 (5)
C20	0.0267 (4)	0.4174 (5)	0.6760 (14)	0.049 (2)	0.534 (5)
H20A	0.0440	0.3872	0.6219	0.059*	0.534 (5)
C21	0.0000	0.3734 (7)	0.7500	0.051 (3)	0.534 (5)
H21A	0.0000	0.3123	0.7500	0.061*	0.534 (5)
N7A	0.0000	0.4041 (6)	0.7500	0.044 (2)	0.466 (5)
N8A	0.04699 (18)	0.4030 (5)	0.5906 (6)	0.102 (2)	0.466 (5)
H8AA	0.0457	0.3466	0.5913	0.122*	0.466 (5)
H8AB	0.0629	0.4293	0.5384	0.122*	0.466 (5)
C19A	0.0240 (4)	0.4504 (6)	0.6714 (13)	0.050 (2)	0.466 (5)
C20A	0.0241 (4)	0.5423 (6)	0.6703 (13)	0.081 (3)	0.466 (5)
H20B	0.0408	0.5729	0.6148	0.097*	0.466 (5)
C21A	0.0000	0.5853 (10)	0.7500	0.093 (5)	0.466 (5)
H21B	0.0000	0.6464	0.7500	0.111*	0.466 (5)
H1N1	0.2349 (8)	0.4278 (15)	0.662 (3)	0.055 (7)*
H1N2	0.2239 (10)	0.648 (2)	0.711 (3)	0.084 (10)*
H2N2	0.2508 (8)	0.5584 (15)	0.754 (3)	0.046 (7)*
H1N3	0.1847 (9)	0.2727 (17)	0.443 (3)	0.057 (8)*
H2N3	0.2216 (8)	0.2915 (15)	0.574 (3)	0.046 (6)*
H1N4	0.1058 (10)	0.1524 (19)	0.422 (3)	0.078 (9)*
H1N5	0.1696 (8)	0.0712 (16)	0.464 (3)	0.053 (8)*
H2N5	0.1805 (10)	0.0010 (18)	0.582 (3)	0.069 (9)*
H1N6	0.0413 (9)	0.2208 (17)	0.353 (3)	0.062 (7)*
H2N6	−0.0011 (9)	0.2076 (16)	0.419 (3)	0.059 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0227 (7)	0.0637 (11)	0.0404 (9)	0.0031 (7)	−0.0057 (6)	0.0151 (8)
O2	0.0254 (6)	0.0651 (10)	0.0233 (7)	0.0144 (7)	−0.0008 (5)	−0.0041 (7)
O3	0.0221 (6)	0.1140 (14)	0.0178 (7)	0.0141 (8)	0.0020 (5)	−0.0077 (8)
O4	0.0169 (6)	0.0635 (10)	0.0354 (8)	0.0058 (6)	0.0042 (5)	−0.0088 (7)
C1	0.0341 (10)	0.0693 (16)	0.0254 (10)	0.0190 (10)	0.0105 (8)	0.0004 (10)
C2	0.0552 (13)	0.0645 (16)	0.0183 (10)	0.0146 (11)	0.0105 (9)	−0.0021 (10)
C3	0.0463 (12)	0.0493 (13)	0.0200 (10)	0.0113 (10)	−0.0078 (8)	−0.0049 (9)
C4	0.0244 (9)	0.0490 (13)	0.0261 (10)	0.0089 (8)	−0.0067 (7)	−0.0089 (9)
C5	0.0206 (8)	0.0492 (12)	0.0185 (9)	0.0091 (8)	−0.0002 (7)	−0.0075 (8)
C6	0.0250 (9)	0.0527 (13)	0.0192 (9)	0.0120 (8)	0.0034 (7)	−0.0010 (8)
C7	0.0198 (8)	0.0584 (14)	0.0231 (9)	0.0049 (8)	0.0014 (7)	−0.0111 (9)
C8	0.0152 (8)	0.0696 (16)	0.0195 (9)	0.0125 (9)	0.0041 (7)	0.0045 (10)
N3	0.0394 (10)	0.0767 (16)	0.0229 (9)	0.0302 (10)	−0.0055 (8)	−0.0076 (10)
N1	0.0186 (7)	0.0658 (13)	0.0223 (8)	0.0113 (8)	0.0044 (6)	0.0089 (8)
N2	0.0203 (8)	0.0636 (14)	0.0411 (11)	−0.0034 (8)	−0.0041 (8)	0.0173 (10)
C9	0.0190 (8)	0.0614 (15)	0.0307 (10)	0.0044 (9)	0.0062 (8)	0.0125 (10)
C10	0.0280 (10)	0.0582 (15)	0.0502 (14)	0.0066 (10)	−0.0063 (10)	0.0122 (12)
C11	0.0271 (10)	0.0734 (18)	0.0424 (13)	0.0163 (11)	−0.0076 (9)	0.0089 (12)
C12	0.0295 (10)	0.0721 (17)	0.0286 (11)	0.0187 (10)	−0.0030 (8)	−0.0025 (11)
C13	0.0264 (9)	0.0711 (16)	0.0184 (9)	0.0164 (10)	0.0063 (8)	0.0009 (10)
N4	0.0241 (8)	0.0920 (16)	0.0210 (8)	0.0174 (9)	−0.0002 (7)	−0.0105 (9)
N5	0.0266 (9)	0.0893 (17)	0.0310 (10)	0.0215 (10)	−0.0029 (8)	−0.0127 (11)
N6	0.0260 (9)	0.133 (2)	0.0329 (11)	0.0320 (11)	0.0098 (8)	0.0162 (12)
C14	0.0260 (9)	0.0796 (17)	0.0239 (10)	0.0151 (10)	−0.0068 (8)	−0.0214 (11)
C15	0.0350 (11)	0.0620 (16)	0.0349 (12)	0.0106 (10)	−0.0042 (9)	−0.0145 (11)
C16	0.0337 (11)	0.0639 (16)	0.0404 (12)	0.0016 (10)	0.0023 (9)	−0.0155 (11)
C17	0.0235 (9)	0.0747 (17)	0.0361 (12)	0.0056 (10)	0.0023 (9)	−0.0184 (11)
C18	0.0217 (9)	0.0897 (18)	0.0231 (10)	0.0156 (10)	−0.0009 (8)	−0.0139 (11)
N7	0.025 (3)	0.032 (4)	0.037 (3)	0.000	−0.006 (2)	0.000
N8	0.0274 (17)	0.056 (2)	0.040 (2)	0.0022 (15)	0.0074 (14)	−0.0074 (16)
C19	0.021 (2)	0.039 (4)	0.037 (3)	0.002 (3)	−0.0130 (19)	0.002 (3)
C20	0.041 (3)	0.032 (4)	0.066 (5)	0.005 (3)	−0.012 (3)	−0.012 (4)
C21	0.032 (4)	0.031 (6)	0.073 (6)	0.000	−0.030 (3)	0.000
N7A	0.044 (4)	0.035 (6)	0.047 (4)	0.000	−0.002 (3)	0.000
N8A	0.060 (3)	0.188 (7)	0.061 (4)	0.063 (4)	0.020 (3)	0.054 (4)
C19A	0.036 (4)	0.055 (6)	0.050 (4)	−0.008 (6)	−0.016 (3)	0.014 (6)
C20A	0.062 (6)	0.063 (6)	0.091 (6)	−0.028 (5)	−0.048 (4)	0.048 (5)
C21A	0.083 (8)	0.038 (8)	0.120 (10)	0.000	−0.070 (6)	0.000

O1—C8	1.275 (3)	N4—H1N4	0.96 (3)
O2—C8	1.250 (3)	N5—C14	1.353 (3)
O3—C7	1.267 (2)	N5—H1N5	0.88 (3)
O4—C7	1.250 (2)	N5—H2N5	0.91 (3)
C1—C2	1.386 (3)	N6—C18	1.341 (3)
C1—C6	1.394 (2)	N6—H1N6	0.92 (3)
C1—H1A	0.9300	N6—H2N6	0.87 (3)
C2—C3	1.379 (3)	C14—C15	1.384 (3)
C2—H2A	0.9300	C15—C16	1.385 (3)
C3—C4	1.378 (3)	C15—H15A	0.9300
C3—H3A	0.9300	C16—C17	1.380 (3)
C4—C5	1.396 (3)	C16—H16A	0.9300
C4—H4A	0.9300	C17—C18	1.387 (3)
C5—C6	1.401 (2)	C17—H17A	0.9300
C5—C7	1.505 (2)	N7—C19i	1.346 (6)
C6—C8	1.508 (3)	N7—C19	1.346 (6)
N3—C13	1.336 (3)	N8—C19	1.373 (7)
N3—H1N3	0.86 (3)	N8—H8A	0.8600
N3—H2N3	0.89 (2)	N8—H8B	0.8600
N1—C9	1.361 (3)	C19—C20	1.401 (7)
N1—C13	1.364 (3)	C20—C21	1.354 (10)
N1—H1N1	0.93 (3)	C20—H20A	0.9300
N2—C9	1.347 (3)	C21—C20i	1.354 (10)
N2—H1N2	1.01 (3)	C21—H21A	0.9300
N2—H2N2	0.83 (2)	N7A—C19Ai	1.348 (10)
C9—C10	1.389 (3)	N7A—C19A	1.348 (10)
C10—C11	1.378 (3)	N8A—C19A	1.351 (10)
C10—H10A	0.9300	N8A—H8AA	0.8600
C11—C12	1.369 (3)	N8A—H8AB	0.8600
C11—H11A	0.9300	C19A—C20A	1.398 (10)
C12—C13	1.393 (3)	C20A—C21A	1.332 (12)
C12—H12A	0.9300	C20A—H20B	0.9300
N4—C14	1.353 (3)	C21A—C20Ai	1.332 (12)
N4—C18	1.371 (2)	C21A—H21B	0.9300
C2—C1—C6	120.62 (18)	C14—N4—H1N4	118.5 (17)
C2—C1—H1A	119.7	C18—N4—H1N4	117.9 (17)
C6—C1—H1A	119.7	C14—N5—H1N5	118.0 (16)
C3—C2—C1	120.05 (18)	C14—N5—H2N5	118.2 (17)
C3—C2—H2A	120.0	H1N5—N5—H2N5	121 (2)
C1—C2—H2A	120.0	C18—N6—H1N6	115.7 (16)
C4—C3—C2	120.00 (18)	C18—N6—H2N6	117.2 (17)
C4—C3—H3A	120.0	H1N6—N6—H2N6	119 (2)
C2—C3—H3A	120.0	N5—C14—N4	117.2 (2)
C3—C4—C5	120.95 (17)	N5—C14—C15	123.9 (2)
C3—C4—H4A	119.5	N4—C14—C15	118.87 (18)
C5—C4—H4A	119.5	C14—C15—C16	118.5 (2)
C4—C5—C6	119.12 (16)	C14—C15—H15A	120.7
C4—C5—C7	119.45 (15)	C16—C15—H15A	120.7
C6—C5—C7	121.41 (16)	C17—C16—C15	122.0 (2)
C1—C6—C5	119.26 (17)	C17—C16—H16A	119.0
C1—C6—C8	116.51 (15)	C15—C16—H16A	119.0
C5—C6—C8	124.20 (15)	C16—C17—C18	118.67 (19)
O4—C7—O3	123.78 (17)	C16—C17—H17A	120.7
O4—C7—C5	118.39 (16)	C18—C17—H17A	120.7
O3—C7—C5	117.83 (15)	N6—C18—N4	116.1 (2)
O2—C8—O1	124.68 (17)	N6—C18—C17	125.55 (18)
O2—C8—C6	118.3 (2)	N4—C18—C17	118.3 (2)
O1—C8—C6	116.80 (19)	C19i—N7—C19	118.3 (7)
C13—N3—H1N3	118.0 (17)	C19—N8—H8A	120.0
C13—N3—H2N3	118.5 (15)	C19—N8—H8B	120.0
H1N3—N3—H2N3	122 (2)	H8A—N8—H8B	120.0
C9—N1—C13	123.73 (17)	N7—C19—N8	115.0 (5)
C9—N1—H1N1	114.9 (15)	N7—C19—C20	121.6 (7)
C13—N1—H1N1	121.2 (15)	N8—C19—C20	123.4 (7)
C9—N2—H1N2	121.1 (17)	C21—C20—C19	118.7 (9)
C9—N2—H2N2	120.2 (17)	C21—C20—H20A	120.6
H1N2—N2—H2N2	119 (2)	C19—C20—H20A	120.6
N2—C9—N1	117.26 (18)	C20i—C21—C20	120.7 (10)
N2—C9—C10	124.7 (2)	C20i—C21—H21A	119.7
N1—C9—C10	118.1 (2)	C20—C21—H21A	119.7
C11—C10—C9	118.8 (2)	C19Ai—N7A—C19A	117.0 (10)
C11—C10—H10A	120.6	C19A—N8A—H8AA	120.0
C9—C10—H10A	120.6	C19A—N8A—H8AB	120.0
C12—C11—C10	122.6 (2)	H8AA—N8A—H8AB	120.0
C12—C11—H11A	118.7	N7A—C19A—N8A	116.2 (8)
C10—C11—H11A	118.7	N7A—C19A—C20A	121.9 (10)
C11—C12—C13	118.4 (2)	N8A—C19A—C20A	121.8 (10)
C11—C12—H12A	120.8	C21A—C20A—C19A	119.0 (12)
C13—C12—H12A	120.8	C21A—C20A—H20B	120.5
N3—C13—N1	116.81 (18)	C19A—C20A—H20B	120.5
N3—C13—C12	124.8 (2)	C20A—C21A—C20Ai	121.1 (14)
N1—C13—C12	118.4 (2)	C20A—C21A—H21B	119.5
C14—N4—C18	123.6 (2)	C20Ai—C21A—H21B	119.5
C6—C1—C2—C3	−0.5 (4)	C9—N1—C13—N3	178.83 (17)
C1—C2—C3—C4	−0.1 (4)	C9—N1—C13—C12	−1.0 (3)
C2—C3—C4—C5	0.4 (3)	C11—C12—C13—N3	−177.8 (2)
C3—C4—C5—C6	−0.2 (3)	C11—C12—C13—N1	2.0 (3)
C3—C4—C5—C7	178.2 (2)	C18—N4—C14—N5	−179.7 (2)
C2—C1—C6—C5	0.7 (3)	C18—N4—C14—C15	−0.6 (3)
C2—C1—C6—C8	−177.5 (2)	N5—C14—C15—C16	−179.8 (2)
C4—C5—C6—C1	−0.4 (3)	N4—C14—C15—C16	1.1 (3)
C7—C5—C6—C1	−178.8 (2)	C14—C15—C16—C17	−0.6 (3)
C4—C5—C6—C8	177.7 (2)	C15—C16—C17—C18	−0.6 (3)
C7—C5—C6—C8	−0.7 (3)	C14—N4—C18—N6	177.5 (2)
C4—C5—C7—O4	0.7 (3)	C14—N4—C18—C17	−0.6 (3)
C6—C5—C7—O4	179.11 (19)	C16—C17—C18—N6	−176.8 (2)
C4—C5—C7—O3	−178.9 (2)	C16—C17—C18—N4	1.2 (3)
C6—C5—C7—O3	−0.5 (3)	C19i—N7—C19—N8	−176.8 (7)
C1—C6—C8—O2	88.3 (2)	C19i—N7—C19—C20	3.0 (8)
C5—C6—C8—O2	−89.8 (2)	N7—C19—C20—C21	−6.0 (16)
C1—C6—C8—O1	−86.7 (2)	N8—C19—C20—C21	173.8 (7)
C5—C6—C8—O1	95.2 (2)	C19—C20—C21—C20i	2.9 (8)
C13—N1—C9—N2	−179.82 (16)	C19Ai—N7A—C19A—N8A	−178.4 (12)
C13—N1—C9—C10	−0.4 (3)	C19Ai—N7A—C19A—C20A	−0.2 (8)
N2—C9—C10—C11	−179.8 (2)	N7A—C19A—C20A—C21A	0.4 (17)
N1—C9—C10—C11	0.8 (3)	N8A—C19A—C20A—C21A	178.5 (9)
C9—C10—C11—C12	0.2 (3)	C19A—C20A—C21A—C20Ai	−0.2 (8)
C10—C11—C12—C13	−1.6 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1ii	0.93 (3)	1.78 (3)	2.697 (2)	170 (2)
N2—H1N2···O2iii	1.01 (3)	1.89 (3)	2.889 (3)	167 (3)
N2—H2N2···O1ii	0.83 (3)	2.48 (2)	3.144 (3)	138 (2)
N3—H1N3···O2	0.86 (3)	2.56 (3)	3.090 (2)	120 (2)
N3—H1N3···O3	0.86 (3)	2.18 (3)	3.005 (3)	161 (3)
N3—H2N3···O2ii	0.89 (3)	2.02 (3)	2.892 (2)	168 (2)
N4—H1N4···O3	0.96 (3)	1.69 (3)	2.641 (2)	169 (3)
N5—H1N5···O3	0.88 (3)	2.53 (3)	3.208 (3)	135 (2)
N5—H2N5···O1iv	0.91 (3)	2.00 (3)	2.886 (3)	166 (2)
N6—H1N6···O4	0.92 (3)	1.96 (3)	2.866 (2)	169 (2)
N6—H2N6···O4v	0.87 (3)	2.02 (3)	2.824 (2)	155 (3)
N8—H8A···O4iii	0.86	2.35	3.196 (4)	170
C15—H15A···O3iv	0.93	2.58	3.422 (3)	151
C10—H10A···Cg1vi	0.93	2.48	3.379 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.93 (3)	1.78 (3)	2.697 (2)	170 (2)
N2—H1N2⋯O2ii	1.01 (3)	1.89 (3)	2.889 (3)	167 (3)
N2—H2N2⋯O1i	0.83 (3)	2.48 (2)	3.144 (3)	138 (2)
N3—H1N3⋯O2	0.86 (3)	2.56 (3)	3.090 (2)	120 (2)
N3—H1N3⋯O3	0.86 (3)	2.18 (3)	3.005 (3)	161 (3)
N3—H2N3⋯O2i	0.89 (3)	2.02 (3)	2.892 (2)	168 (2)
N4—H1N4⋯O3	0.96 (3)	1.69 (3)	2.641 (2)	169 (3)
N5—H1N5⋯O3	0.88 (3)	2.53 (3)	3.208 (3)	135 (2)
N5—H2N5⋯O1iii	0.91 (3)	2.00 (3)	2.886 (3)	166 (2)
N6—H1N6⋯O4	0.92 (3)	1.96 (3)	2.866 (2)	169 (2)
N6—H2N6⋯O4iv	0.87 (3)	2.02 (3)	2.824 (2)	155 (3)
N8—H8A⋯O4ii	0.86	2.35	3.196 (4)	170
C15—H15A⋯O3iii	0.93	2.58	3.422 (3)	151
C10—H10A⋯Cg1v	0.93	2.48	3.379 (3)	163

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of the C1–C6 ring.