Triprolidinium dipicrate.

In the tripodinium cation of the title compound {systematic name: 2-[(E)-1-(4-methyl-phen-yl)-3-(pyrrolidin-1-ium-1-yl)prop-1-en-yl]pyridinium bis-(2,4,6-trinitro-phenolate)}, C(19)H(24)N(2) (+)·2C(6)H(2)N(3)O(7) (-), the N atoms on both the pyrrolidine and pyridinium groups are protonated. The pyrrolidine group adopts a slightly distorted envelope configuration. Strong N-H⋯O cation-anion hydrogen bonds and weak inter-molecular N-H⋯O inter-actions link the dication and two anions. In both picrate anions, the nitro groups display rotational disorder over two orientations in a 0.605 (6):0.395 (6) ratio. The crystal packing also features weak inter-molecular π-π [centroid-centroid distance = 3.8036 (14) Å] and C-H⋯O inter-actions.

Related literature

For anti­cholinergic properties, see: Salunga et al. (1996 ▶). For related structures, see: James & Williams (1971 ▶, 1974 ▶); Parvez & Sabir (1997 ▶). For puckering paramerers, see: Cremer & Pople (1975 ▶). For bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C19H24N2 2+·2C6H2N3O7 −

M = 736.61

Monoclinic,

a = 15.0542 (7) Å

b = 12.7489 (5) Å

c = 17.1446 (7) Å

β = 100.218 (4)°

V = 3238.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 173 K

0.34 × 0.23 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010 ▶) T min = 0.960, T max = 0.975

32796 measured reflections

8355 independent reflections

6144 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.192

S = 1.02

8355 reflections

486 parameters

14 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.42 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681103457X/xu5298sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681103457X/xu5298Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681103457X/xu5298Isup3.cml

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

C19H24N22+·2C6H2N3O7−	F(000) = 1528
Mr = 736.61	Dx = 1.511 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 11024 reflections
a = 15.0542 (7) Å	θ = 3.2–32.3°
b = 12.7489 (5) Å	µ = 0.12 mm−1
c = 17.1446 (7) Å	T = 173 K
β = 100.218 (4)°	Block, colorless
V = 3238.3 (2) Å3	0.34 × 0.23 × 0.21 mm
Z = 4

Oxford Diffraction Xcalibur Eos Gemini diffractometer	8355 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6144 reflections with I > 2σ(I)
graphite	Rint = 0.027
Detector resolution: 16.1500 pixels mm-1	θmax = 28.7°, θmin = 3.2°
ω scans	h = −20→20
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	k = −17→17
Tmin = 0.960, Tmax = 0.975	l = −22→23
32796 measured reflections

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.087P)2 + 2.0922P] where P = (Fo2 + 2Fc2)/3
8355 reflections	(Δ/σ)max = 0.019
486 parameters	Δρmax = 0.63 e Å−3
14 restraints	Δρmin = −0.42 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 > 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	0.92233 (17)	0.70372 (18)	0.04819 (15)	0.0835 (7)
O2	0.82310 (14)	0.65125 (19)	0.11427 (12)	0.0733 (6)
O3	0.88982 (12)	0.56044 (14)	0.25150 (11)	0.0561 (4)
O4A	0.9819 (13)	0.4781 (13)	0.3699 (8)	0.0957 (11)	0.395 (6)
O4	0.9885 (8)	0.4552 (8)	0.3767 (5)	0.0957 (11)	0.605 (6)
O5A	1.0956 (6)	0.3773 (8)	0.3664 (5)	0.0957 (11)	0.395 (6)
O5	1.0589 (4)	0.3329 (5)	0.3390 (3)	0.0957 (11)	0.605 (6)
O6	1.22955 (16)	0.3894 (2)	0.13260 (14)	0.0886 (8)
O7	1.17901 (14)	0.49452 (17)	0.03706 (11)	0.0650 (5)
O8A	0.3039 (6)	0.1518 (9)	0.1006 (6)	0.0706 (12)	0.395 (6)
O8	0.3337 (4)	0.1253 (5)	0.1125 (4)	0.0706 (12)	0.605 (6)
O9A	0.2177 (6)	0.0413 (8)	0.1356 (6)	0.0706 (12)	0.395 (6)
O9	0.2512 (4)	0.0092 (5)	0.1496 (3)	0.0706 (12)	0.605 (6)
O10	0.41754 (11)	0.24944 (14)	0.22274 (9)	0.0496 (4)
O11	0.42811 (13)	0.42582 (16)	0.31111 (14)	0.0662 (5)
O12	0.42006 (17)	0.3801 (2)	0.43080 (13)	0.0884 (8)
O13	0.1432 (6)	0.1580 (6)	0.4551 (6)	0.0708 (7)	0.395 (6)
O13A	0.1624 (3)	0.1919 (4)	0.4605 (4)	0.0708 (7)	0.605 (6)
O14	0.0765 (6)	0.0945 (9)	0.3400 (4)	0.0708 (7)	0.395 (6)
O14A	0.0865 (4)	0.0942 (5)	0.3683 (3)	0.0708 (7)	0.605 (6)
N1	0.48222 (11)	0.27782 (13)	0.08706 (9)	0.0334 (4)
H1N	0.4503 (15)	0.2601 (19)	0.1214 (12)	0.040*
N2	0.77333 (12)	0.47437 (14)	0.33144 (10)	0.0385 (4)
H2N	0.8096 (15)	0.483 (2)	0.2986 (13)	0.046*
N3	0.89847 (15)	0.64836 (17)	0.09876 (12)	0.0513 (5)
N4	1.02831 (16)	0.42310 (19)	0.32931 (13)	0.0576 (6)
N5	1.17391 (15)	0.45175 (18)	0.10008 (13)	0.0532 (5)
N6	0.27963 (15)	0.10320 (18)	0.15556 (12)	0.0529 (5)
N7	0.40122 (14)	0.36817 (18)	0.35907 (13)	0.0545 (5)
N8	0.14695 (19)	0.1484 (2)	0.39024 (16)	0.0692 (7)
C1	0.46460 (15)	0.20288 (18)	0.01772 (12)	0.0409 (5)
H1A	0.5179	0.1975	−0.0085	0.049*
H1B	0.4493	0.1321	0.0351	0.049*
C2	0.3856 (2)	0.2509 (2)	−0.03715 (16)	0.0621 (7)
H2A	0.3894	0.2359	−0.0931	0.075*
H2B	0.3280	0.2226	−0.0259	0.075*
C3	0.3918 (2)	0.3664 (3)	−0.0214 (2)	0.0748 (9)
H3A	0.4153	0.4027	−0.0646	0.090*
H3B	0.3314	0.3951	−0.0186	0.090*
C4	0.4532 (3)	0.3821 (2)	0.05422 (19)	0.0839 (11)
H4A	0.4219	0.4208	0.0916	0.101*
H4B	0.5063	0.4236	0.0459	0.101*
C5	0.57653 (15)	0.2711 (2)	0.12893 (15)	0.0531 (6)
H5A	0.6172	0.2871	0.0910	0.064*
H5B	0.5889	0.1982	0.1477	0.064*
C6	0.59780 (15)	0.3441 (2)	0.19836 (13)	0.0452 (5)
H6A	0.5496	0.3785	0.2170	0.054*
C7	0.68177 (14)	0.36208 (17)	0.23445 (11)	0.0363 (4)
C8	0.69781 (13)	0.41772 (16)	0.31109 (11)	0.0343 (4)
C9	0.64044 (16)	0.4112 (2)	0.36606 (13)	0.0447 (5)
H9A	0.5864	0.3714	0.3540	0.054*
C10	0.66114 (19)	0.4620 (2)	0.43778 (14)	0.0545 (6)
H10A	0.6211	0.4578	0.4748	0.065*
C11	0.7398 (2)	0.5186 (2)	0.45588 (13)	0.0536 (6)
H11A	0.7553	0.5533	0.5055	0.064*
C12	0.79475 (18)	0.52380 (19)	0.40122 (13)	0.0496 (6)
H12A	0.8492	0.5630	0.4126	0.059*
C13	0.76235 (13)	0.31890 (16)	0.20509 (11)	0.0343 (4)
C14	0.81005 (15)	0.23621 (19)	0.24497 (12)	0.0434 (5)
H14A	0.7913	0.2075	0.2906	0.052*
C15	0.88497 (16)	0.19494 (19)	0.21895 (14)	0.0465 (5)
H15A	0.9171	0.1386	0.2473	0.056*
C16	0.91379 (14)	0.23425 (17)	0.15237 (13)	0.0395 (5)
C17	0.86463 (15)	0.31561 (19)	0.11187 (13)	0.0436 (5)
H17A	0.8822	0.3426	0.0653	0.052*
C18	0.79042 (15)	0.35835 (18)	0.13792 (13)	0.0418 (5)
H18A	0.7586	0.4150	0.1097	0.050*
C19	0.99617 (17)	0.1905 (2)	0.12528 (17)	0.0578 (6)
H19A	0.9904	0.1999	0.0679	0.087*
H19B	1.0017	0.1156	0.1381	0.087*
H19C	1.0500	0.2276	0.1522	0.087*
C20	0.96436 (15)	0.57494 (16)	0.14058 (12)	0.0378 (4)
C21	0.95360 (15)	0.53588 (16)	0.21766 (13)	0.0399 (5)
C22	1.02623 (16)	0.46581 (18)	0.25059 (13)	0.0430 (5)
C23	1.09501 (16)	0.43644 (18)	0.21281 (14)	0.0452 (5)
H23A	1.1395	0.3880	0.2369	0.054*
C24	1.09888 (15)	0.47827 (17)	0.13884 (13)	0.0414 (5)
C25	1.03443 (15)	0.54831 (17)	0.10349 (12)	0.0389 (4)
H25A	1.0386	0.5780	0.0535	0.047*
C26	0.28089 (15)	0.15781 (17)	0.22957 (12)	0.0396 (5)
C27	0.35152 (13)	0.23267 (16)	0.25547 (11)	0.0356 (4)
C28	0.34105 (14)	0.28230 (18)	0.32932 (12)	0.0403 (5)
C29	0.27778 (17)	0.25319 (19)	0.37352 (13)	0.0472 (6)
H29A	0.2772	0.2848	0.4236	0.057*
C30	0.21500 (17)	0.1777 (2)	0.34464 (14)	0.0492 (6)
C31	0.21513 (16)	0.13026 (18)	0.27218 (14)	0.0453 (5)
H31A	0.1706	0.0796	0.2521	0.054*

	U11	U22	U33	U12	U13	U23
O1	0.0933 (16)	0.0729 (14)	0.0937 (16)	0.0258 (12)	0.0423 (13)	0.0435 (12)
O2	0.0577 (12)	0.0972 (16)	0.0691 (12)	0.0240 (11)	0.0224 (10)	0.0111 (11)
O3	0.0602 (11)	0.0571 (10)	0.0597 (10)	−0.0013 (8)	0.0343 (9)	0.0068 (8)
O4A	0.126 (2)	0.110 (4)	0.0594 (17)	0.054 (2)	0.0387 (17)	0.0402 (14)
O4	0.126 (2)	0.110 (4)	0.0594 (17)	0.054 (2)	0.0387 (17)	0.0402 (14)
O5A	0.126 (2)	0.110 (4)	0.0594 (17)	0.054 (2)	0.0387 (17)	0.0402 (14)
O5	0.126 (2)	0.110 (4)	0.0594 (17)	0.054 (2)	0.0387 (17)	0.0402 (14)
O6	0.0714 (14)	0.116 (2)	0.0838 (15)	0.0450 (14)	0.0276 (12)	0.0182 (14)
O7	0.0716 (13)	0.0776 (13)	0.0537 (10)	0.0064 (10)	0.0325 (9)	−0.0010 (9)
O8A	0.077 (3)	0.083 (3)	0.058 (2)	−0.030 (2)	0.030 (2)	−0.0174 (18)
O8	0.077 (3)	0.083 (3)	0.058 (2)	−0.030 (2)	0.030 (2)	−0.0174 (18)
O9A	0.077 (3)	0.083 (3)	0.058 (2)	−0.030 (2)	0.030 (2)	−0.0174 (18)
O9	0.077 (3)	0.083 (3)	0.058 (2)	−0.030 (2)	0.030 (2)	−0.0174 (18)
O10	0.0442 (9)	0.0685 (11)	0.0417 (8)	−0.0085 (8)	0.0227 (7)	−0.0043 (7)
O11	0.0522 (11)	0.0573 (11)	0.0923 (15)	−0.0053 (9)	0.0221 (10)	−0.0129 (11)
O12	0.0864 (16)	0.1094 (19)	0.0609 (12)	0.0143 (14)	−0.0106 (11)	−0.0316 (13)
O13	0.0794 (16)	0.0789 (14)	0.0695 (15)	0.0012 (12)	0.0548 (18)	0.025 (2)
O13A	0.0794 (16)	0.0789 (14)	0.0695 (15)	0.0012 (12)	0.0548 (18)	0.025 (2)
O14	0.0794 (16)	0.0789 (14)	0.0695 (15)	0.0012 (12)	0.0548 (18)	0.025 (2)
O14A	0.0794 (16)	0.0789 (14)	0.0695 (15)	0.0012 (12)	0.0548 (18)	0.025 (2)
N1	0.0337 (8)	0.0413 (9)	0.0275 (7)	−0.0007 (7)	0.0115 (6)	−0.0027 (6)
N2	0.0427 (10)	0.0439 (9)	0.0312 (8)	−0.0069 (8)	0.0131 (7)	−0.0020 (7)
N3	0.0564 (12)	0.0488 (11)	0.0513 (11)	0.0073 (9)	0.0169 (10)	0.0010 (9)
N4	0.0621 (14)	0.0641 (14)	0.0504 (12)	0.0035 (11)	0.0199 (10)	0.0177 (10)
N5	0.0503 (12)	0.0612 (13)	0.0506 (11)	0.0047 (10)	0.0161 (10)	−0.0064 (10)
N6	0.0548 (12)	0.0615 (13)	0.0462 (10)	−0.0188 (10)	0.0193 (9)	−0.0072 (9)
N7	0.0426 (11)	0.0619 (13)	0.0572 (12)	0.0133 (10)	0.0038 (10)	−0.0164 (11)
N8	0.0687 (16)	0.0702 (15)	0.0831 (17)	0.0250 (13)	0.0529 (14)	0.0322 (13)
C1	0.0466 (12)	0.0449 (11)	0.0322 (9)	−0.0044 (9)	0.0094 (9)	−0.0069 (8)
C2	0.0660 (17)	0.0691 (17)	0.0445 (13)	−0.0034 (13)	−0.0085 (12)	0.0011 (12)
C3	0.0715 (19)	0.0651 (18)	0.077 (2)	0.0079 (15)	−0.0153 (16)	0.0112 (15)
C4	0.133 (3)	0.0419 (14)	0.0646 (17)	0.0206 (17)	−0.0165 (19)	−0.0034 (13)
C5	0.0363 (11)	0.0741 (17)	0.0498 (13)	0.0015 (11)	0.0102 (10)	−0.0227 (12)
C6	0.0361 (11)	0.0600 (14)	0.0414 (11)	−0.0013 (10)	0.0120 (9)	−0.0148 (10)
C7	0.0358 (10)	0.0438 (11)	0.0314 (9)	−0.0020 (8)	0.0118 (8)	−0.0038 (8)
C8	0.0334 (10)	0.0390 (10)	0.0323 (9)	0.0011 (8)	0.0107 (8)	0.0012 (8)
C9	0.0409 (11)	0.0579 (13)	0.0390 (10)	−0.0003 (10)	0.0173 (9)	0.0013 (10)
C10	0.0634 (16)	0.0695 (16)	0.0365 (11)	0.0107 (13)	0.0247 (11)	0.0009 (11)
C11	0.0757 (18)	0.0528 (14)	0.0334 (10)	0.0053 (12)	0.0124 (11)	−0.0094 (10)
C12	0.0606 (15)	0.0464 (12)	0.0405 (11)	−0.0087 (11)	0.0057 (10)	−0.0055 (9)
C13	0.0305 (9)	0.0427 (11)	0.0307 (9)	−0.0043 (8)	0.0080 (7)	−0.0061 (8)
C14	0.0442 (12)	0.0559 (13)	0.0307 (9)	0.0012 (10)	0.0081 (9)	0.0037 (9)
C15	0.0438 (12)	0.0508 (13)	0.0441 (11)	0.0097 (10)	0.0055 (9)	0.0043 (10)
C16	0.0326 (10)	0.0449 (11)	0.0414 (10)	−0.0023 (8)	0.0073 (8)	−0.0108 (9)
C17	0.0431 (12)	0.0525 (13)	0.0393 (10)	−0.0011 (10)	0.0185 (9)	0.0025 (9)
C18	0.0380 (11)	0.0482 (12)	0.0419 (11)	0.0028 (9)	0.0142 (9)	0.0072 (9)
C19	0.0445 (13)	0.0637 (16)	0.0689 (16)	0.0064 (12)	0.0195 (12)	−0.0130 (13)
C20	0.0415 (11)	0.0345 (10)	0.0388 (10)	−0.0045 (8)	0.0106 (8)	−0.0029 (8)
C21	0.0454 (11)	0.0355 (10)	0.0415 (10)	−0.0101 (9)	0.0150 (9)	−0.0034 (8)
C22	0.0504 (13)	0.0427 (11)	0.0371 (10)	−0.0085 (9)	0.0110 (9)	0.0032 (9)
C23	0.0468 (12)	0.0443 (12)	0.0436 (11)	−0.0016 (9)	0.0057 (10)	0.0007 (9)
C24	0.0420 (11)	0.0445 (11)	0.0393 (10)	−0.0032 (9)	0.0119 (9)	−0.0087 (9)
C25	0.0452 (11)	0.0396 (11)	0.0333 (9)	−0.0069 (9)	0.0110 (9)	−0.0046 (8)
C26	0.0403 (11)	0.0445 (11)	0.0371 (10)	0.0021 (9)	0.0149 (9)	0.0050 (8)
C27	0.0339 (10)	0.0432 (11)	0.0316 (9)	0.0058 (8)	0.0115 (8)	0.0052 (8)
C28	0.0385 (11)	0.0459 (11)	0.0380 (10)	0.0119 (9)	0.0109 (8)	0.0003 (9)
C29	0.0532 (13)	0.0560 (13)	0.0369 (10)	0.0233 (11)	0.0205 (10)	0.0074 (10)
C30	0.0509 (13)	0.0522 (13)	0.0531 (13)	0.0174 (11)	0.0328 (11)	0.0201 (11)
C31	0.0415 (11)	0.0444 (12)	0.0540 (13)	0.0032 (9)	0.0198 (10)	0.0116 (10)

O1—N3	1.220 (3)	C5—H5A	0.9900
O2—N3	1.211 (3)	C5—H5B	0.9900
O3—C21	1.247 (3)	C6—C7	1.325 (3)
O4A—N4	1.280 (11)	C6—H6A	0.9500
O4—N4	1.166 (7)	C7—C8	1.475 (3)
O5A—N4	1.242 (9)	C7—C13	1.498 (3)
O5—N4	1.238 (6)	C8—C9	1.389 (3)
O6—N5	1.216 (3)	C9—C10	1.375 (3)
O7—N5	1.225 (3)	C9—H9A	0.9500
O8A—N6	1.235 (10)	C10—C11	1.374 (4)
O8—N6	1.225 (6)	C10—H10A	0.9500
O9A—N6	1.224 (10)	C11—C12	1.358 (4)
O9—N6	1.270 (6)	C11—H11A	0.9500
O10—C27	1.244 (2)	C12—H12A	0.9500
O11—N7	1.224 (3)	C13—C14	1.386 (3)
O12—N7	1.222 (3)	C13—C18	1.389 (3)
O13—N8	1.130 (10)	C14—C15	1.388 (3)
O13A—N8	1.309 (7)	C14—H14A	0.9500
O14—N8	1.419 (12)	C15—C16	1.385 (3)
O14A—N8	1.152 (8)	C15—H15A	0.9500
N1—C5	1.475 (3)	C16—C17	1.387 (3)
N1—C4	1.480 (3)	C16—C19	1.506 (3)
N1—C1	1.511 (3)	C17—C18	1.386 (3)
N1—H1N	0.854 (16)	C17—H17A	0.9500
N2—C8	1.340 (3)	C18—H18A	0.9500
N2—C12	1.340 (3)	C19—H19A	0.9800
N2—H2N	0.858 (17)	C19—H19B	0.9800
N3—C20	1.457 (3)	C19—H19C	0.9800
N4—C22	1.451 (3)	C20—C25	1.368 (3)
N5—C24	1.448 (3)	C20—C21	1.448 (3)
N6—C26	1.445 (3)	C21—C22	1.447 (3)
N7—C28	1.454 (3)	C22—C23	1.367 (3)
N8—C30	1.444 (3)	C23—C24	1.386 (3)
C1—C2	1.509 (3)	C23—H23A	0.9500
C1—H1A	0.9900	C24—C25	1.378 (3)
C1—H1B	0.9900	C25—H25A	0.9500
C2—C3	1.497 (4)	C26—C31	1.376 (3)
C2—H2A	0.9900	C26—C27	1.439 (3)
C2—H2B	0.9900	C27—C28	1.449 (3)
C3—C4	1.467 (4)	C28—C29	1.369 (3)
C3—H3A	0.9900	C29—C30	1.378 (4)
C3—H3B	0.9900	C29—H29A	0.9500
C4—H4A	0.9900	C30—C31	1.382 (3)
C4—H4B	0.9900	C31—H31A	0.9500
C5—C6	1.501 (3)
C5—N1—C4	115.6 (2)	C8—C7—C13	117.49 (17)
C5—N1—C1	111.42 (16)	N2—C8—C9	117.15 (19)
C4—N1—C1	105.67 (18)	N2—C8—C7	119.24 (17)
C5—N1—H1N	105.1 (16)	C9—C8—C7	123.55 (19)
C4—N1—H1N	109.6 (17)	C10—C9—C8	120.6 (2)
C1—N1—H1N	109.5 (16)	C10—C9—H9A	119.7
C8—N2—C12	123.00 (19)	C8—C9—H9A	119.7
C8—N2—H2N	120.3 (17)	C11—C10—C9	119.9 (2)
C12—N2—H2N	116.6 (18)	C11—C10—H10A	120.0
O2—N3—O1	122.9 (2)	C9—C10—H10A	120.0
O2—N3—C20	119.6 (2)	C12—C11—C10	118.4 (2)
O1—N3—C20	117.4 (2)	C12—C11—H11A	120.8
O4—N4—O5	117.2 (4)	C10—C11—H11A	120.8
O4—N4—O5A	106.4 (6)	N2—C12—C11	120.9 (2)
O5—N4—O4A	131.5 (5)	N2—C12—H12A	119.5
O4—N4—C22	126.0 (3)	C11—C12—H12A	119.5
O5—N4—C22	114.8 (3)	C14—C13—C18	118.50 (19)
O5A—N4—C22	122.3 (4)	C14—C13—C7	119.56 (18)
O4A—N4—C22	112.1 (4)	C18—C13—C7	121.93 (19)
O6—N5—O7	123.3 (2)	C13—C14—C15	120.6 (2)
O6—N5—C24	118.2 (2)	C13—C14—H14A	119.7
O7—N5—C24	118.5 (2)	C15—C14—H14A	119.7
O9A—N6—O8	122.3 (4)	C16—C15—C14	121.3 (2)
O9A—N6—O8A	115.1 (8)	C16—C15—H15A	119.4
O8—N6—O9	114.8 (5)	C14—C15—H15A	119.4
O8A—N6—O9	123.6 (5)	C15—C16—C17	117.8 (2)
O9A—N6—C26	116.6 (5)	C15—C16—C19	121.0 (2)
O8—N6—C26	120.8 (4)	C17—C16—C19	121.2 (2)
O8A—N6—C26	117.9 (6)	C18—C17—C16	121.5 (2)
O9—N6—C26	118.5 (3)	C18—C17—H17A	119.3
O12—N7—O11	123.8 (3)	C16—C17—H17A	119.3
O12—N7—C28	117.8 (3)	C17—C18—C13	120.4 (2)
O11—N7—C28	118.4 (2)	C17—C18—H18A	119.8
O13—N8—O14A	102.2 (4)	C13—C18—H18A	119.8
O14A—N8—O13A	123.8 (3)	C16—C19—H19A	109.5
O13—N8—O14	119.2 (5)	C16—C19—H19B	109.5
O13A—N8—O14	139.1 (4)	H19A—C19—H19B	109.5
O13—N8—C30	132.0 (5)	C16—C19—H19C	109.5
O14A—N8—C30	125.0 (3)	H19A—C19—H19C	109.5
O13A—N8—C30	111.2 (3)	H19B—C19—H19C	109.5
O14—N8—C30	108.8 (3)	C25—C20—C21	124.0 (2)
C2—C1—N1	104.05 (19)	C25—C20—N3	116.41 (19)
C2—C1—H1A	110.9	C21—C20—N3	119.58 (19)
N1—C1—H1A	110.9	O3—C21—C22	124.4 (2)
C2—C1—H1B	110.9	O3—C21—C20	124.0 (2)
N1—C1—H1B	110.9	C22—C21—C20	111.67 (19)
H1A—C1—H1B	109.0	C23—C22—C21	124.6 (2)
C3—C2—C1	105.7 (2)	C23—C22—N4	116.4 (2)
C3—C2—H2A	110.6	C21—C22—N4	119.0 (2)
C1—C2—H2A	110.6	C22—C23—C24	119.1 (2)
C3—C2—H2B	110.6	C22—C23—H23A	120.5
C1—C2—H2B	110.6	C24—C23—H23A	120.5
H2A—C2—H2B	108.7	C25—C24—C23	120.7 (2)
C4—C3—C2	107.6 (2)	C25—C24—N5	119.7 (2)
C4—C3—H3A	110.2	C23—C24—N5	119.5 (2)
C2—C3—H3A	110.2	C20—C25—C24	119.84 (19)
C4—C3—H3B	110.2	C20—C25—H25A	120.1
C2—C3—H3B	110.2	C24—C25—H25A	120.1
H3A—C3—H3B	108.5	C31—C26—C27	124.6 (2)
C3—C4—N1	108.1 (2)	C31—C26—N6	116.4 (2)
C3—C4—H4A	110.1	C27—C26—N6	118.99 (18)
N1—C4—H4A	110.1	O10—C27—C26	125.50 (19)
C3—C4—H4B	110.1	O10—C27—C28	122.6 (2)
N1—C4—H4B	110.1	C26—C27—C28	111.73 (18)
H4A—C4—H4B	108.4	C29—C28—C27	124.0 (2)
N1—C5—C6	113.65 (19)	C29—C28—N7	117.4 (2)
N1—C5—H5A	108.8	C27—C28—N7	118.53 (19)
C6—C5—H5A	108.8	C28—C29—C30	119.4 (2)
N1—C5—H5B	108.8	C28—C29—H29A	120.3
C6—C5—H5B	108.8	C30—C29—H29A	120.3
H5A—C5—H5B	107.7	C29—C30—C31	121.2 (2)
C7—C6—C5	122.0 (2)	C29—C30—N8	119.6 (2)
C7—C6—H6A	119.0	C31—C30—N8	119.2 (3)
C5—C6—H6A	119.0	C26—C31—C30	118.8 (2)
C6—C7—C8	119.40 (18)	C26—C31—H31A	120.6
C6—C7—C13	122.81 (18)	C30—C31—H31A	120.6
C5—N1—C1—C2	−155.6 (2)	O4A—N4—C22—C23	158.7 (12)
C4—N1—C1—C2	−29.3 (3)	O4—N4—C22—C21	−17.2 (10)
N1—C1—C2—C3	27.9 (3)	O5—N4—C22—C21	146.1 (4)
C1—C2—C3—C4	−16.3 (4)	O5A—N4—C22—C21	−167.7 (7)
C2—C3—C4—N1	−2.2 (4)	O4A—N4—C22—C21	−20.9 (13)
C5—N1—C4—C3	143.4 (3)	C21—C22—C23—C24	2.3 (4)
C1—N1—C4—C3	19.7 (4)	N4—C22—C23—C24	−177.2 (2)
C4—N1—C5—C6	59.3 (3)	C22—C23—C24—C25	−0.1 (3)
C1—N1—C5—C6	179.9 (2)	C22—C23—C24—N5	176.9 (2)
N1—C5—C6—C7	−168.2 (2)	O6—N5—C24—C25	−179.8 (2)
C5—C6—C7—C8	−168.2 (2)	O7—N5—C24—C25	1.5 (3)
C5—C6—C7—C13	5.4 (4)	O6—N5—C24—C23	3.1 (4)
C12—N2—C8—C9	−0.1 (3)	O7—N5—C24—C23	−175.6 (2)
C12—N2—C8—C7	−177.3 (2)	C21—C20—C25—C24	1.7 (3)
C6—C7—C8—N2	−151.8 (2)	N3—C20—C25—C24	−179.20 (19)
C13—C7—C8—N2	34.2 (3)	C23—C24—C25—C20	−1.8 (3)
C6—C7—C8—C9	31.2 (3)	N5—C24—C25—C20	−178.9 (2)
C13—C7—C8—C9	−142.8 (2)	O9A—N6—C26—C31	3.5 (6)
N2—C8—C9—C10	0.4 (3)	O8—N6—C26—C31	177.4 (4)
C7—C8—C9—C10	177.5 (2)	O8A—N6—C26—C31	146.8 (5)
C8—C9—C10—C11	−0.8 (4)	O9—N6—C26—C31	−31.1 (4)
C9—C10—C11—C12	0.8 (4)	O9A—N6—C26—C27	−179.2 (5)
C8—N2—C12—C11	0.1 (4)	O8—N6—C26—C27	−5.2 (5)
C10—C11—C12—N2	−0.5 (4)	O8A—N6—C26—C27	−35.9 (6)
C6—C7—C13—C14	−105.8 (3)	O9—N6—C26—C27	146.2 (4)
C8—C7—C13—C14	67.9 (3)	C31—C26—C27—O10	170.8 (2)
C6—C7—C13—C18	73.2 (3)	N6—C26—C27—O10	−6.3 (3)
C8—C7—C13—C18	−113.0 (2)	C31—C26—C27—C28	−4.7 (3)
C18—C13—C14—C15	1.0 (3)	N6—C26—C27—C28	178.24 (19)
C7—C13—C14—C15	−179.9 (2)	O10—C27—C28—C29	−168.8 (2)
C13—C14—C15—C16	−0.5 (4)	C26—C27—C28—C29	6.9 (3)
C14—C15—C16—C17	−0.7 (3)	O10—C27—C28—N7	11.0 (3)
C14—C15—C16—C19	178.8 (2)	C26—C27—C28—N7	−173.36 (18)
C15—C16—C17—C18	1.6 (3)	O12—N7—C28—C29	30.3 (3)
C19—C16—C17—C18	−178.0 (2)	O11—N7—C28—C29	−147.8 (2)
C16—C17—C18—C13	−1.2 (3)	O12—N7—C28—C27	−149.5 (2)
C14—C13—C18—C17	−0.1 (3)	O11—N7—C28—C27	32.4 (3)
C7—C13—C18—C17	−179.2 (2)	C27—C28—C29—C30	−5.1 (3)
O2—N3—C20—C25	157.6 (2)	N7—C28—C29—C30	175.1 (2)
O1—N3—C20—C25	−21.4 (3)	C28—C29—C30—C31	0.5 (3)
O2—N3—C20—C21	−23.2 (3)	C28—C29—C30—N8	−178.6 (2)
O1—N3—C20—C21	157.8 (2)	O13—N8—C30—C29	−19.7 (7)
C25—C20—C21—O3	179.8 (2)	O14A—N8—C30—C29	172.0 (4)
N3—C20—C21—O3	0.7 (3)	O13A—N8—C30—C29	−7.8 (4)
C25—C20—C21—C22	0.3 (3)	O14—N8—C30—C29	163.1 (4)
N3—C20—C21—C22	−178.81 (19)	O13—N8—C30—C31	161.1 (6)
O3—C21—C22—C23	178.2 (2)	O14A—N8—C30—C31	−7.1 (5)
C20—C21—C22—C23	−2.3 (3)	O13A—N8—C30—C31	173.1 (3)
O3—C21—C22—N4	−2.3 (3)	O14—N8—C30—C31	−16.0 (5)
C20—C21—C22—N4	177.22 (19)	C27—C26—C31—C30	0.8 (3)
O4—N4—C22—C23	162.4 (10)	N6—C26—C31—C30	177.9 (2)
O5—N4—C22—C23	−34.3 (5)	C29—C30—C31—C26	1.6 (3)
O5A—N4—C22—C23	11.9 (7)	N8—C30—C31—C26	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O10	0.85 (2)	1.89 (2)	2.701 (2)	157 (2)
N1—H1N···O8	0.85 (2)	2.44 (2)	3.053 (7)	129 (2)
N1—H1N···O8A	0.85 (2)	2.57 (2)	3.173 (10)	128 (2)
N2—H2N···O3	0.86 (2)	1.85 (2)	2.648 (2)	153 (2)
C31—H31A···O11i	0.95	2.58	3.520 (3)	170.
C9—H9A···O11	0.95	2.47	3.174 (3)	131.
C5—H5B···O3ii	0.99	2.44	3.362 (4)	154.
C5—H5A···O13Aiii	0.99	2.47	3.399 (6)	157.
C4—H4A···O14Aiv	0.99	2.33	3.116 (7)	136.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O10	0.85 (2)	1.89 (2)	2.701 (2)	157 (2)
N1—H1N⋯O8	0.85 (2)	2.44 (2)	3.053 (7)	129 (2)
N1—H1N⋯O8A	0.85 (2)	2.57 (2)	3.173 (10)	128 (2)
N2—H2N⋯O3	0.86 (2)	1.85 (2)	2.648 (2)	153 (2)
C31—H31A⋯O11i	0.95	2.58	3.520 (3)	170
C9—H9A⋯O11	0.95	2.47	3.174 (3)	131
C5—H5B⋯O3ii	0.99	2.44	3.362 (4)	154
C5—H5A⋯O13Aiii	0.99	2.47	3.399 (6)	157
C4—H4A⋯O14Aiv	0.99	2.33	3.116 (7)	136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .