Unanti­cipated formation of a novel octa­aza­cyclo­decane ring upon oxidation of a 1,1-bis-urazole

Tetra­hydro­tetra­zoles are a little-explored class of five-membered heterocycles with four contiguous singly-bonded N atoms. Recent work in our labs has demonstrated that urazole radicals are amenable to N—N bond formation via radical combination to form such a chain of four N atoms. Previously described 1,1-bis-urazole compounds appeared to be convenient precursors to the target tetra­zoles via their oxidation to inter­mediate urazole diradicals, which upon N—N bond formation would complete the tetra­zole framework. While oxidation proceeded smoothly, the novel 10-membered octa­aza heterocycle 7,7,18,18-tetra­acetyl-4,10,15,21-tetra­phenyl-1,2,4,6,8,10,12,13,15,17,19,21-do­deca­aza­penta­cyclo­[17.3.0.0^2,6.0^8,12.0^13,17]docosan-3,5,9,11,14,16,20,22-octone, C₄₂H₃₂N₁₂O₁₂, was obtained (36% yield) instead of the expected tetra­zole product, as confirmed by X-ray crystallography. Calculations at the (U)B3LYP/6-311G(d,p) level of theory suggest that the desired tetra­zoles have weak N—N bonds connecting the two urazole units.

Computing details

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: shelXle (Hübschle et al., 2011); software used to prepare material for publication: shelXle (Hübschle et al., 2011).

7,7,18,18-Tetraacetyl-4,10,15,21-tetraphenyl-1,2,4,6,8,10,12,13,15,17,19,21-dodecaazapentacyclo[17.3.0.02,6.08,12.013,17]docosan-3,5,9,11,14,16,20,22-octone

Crystal data

C42H32N12O12	F(000) = 928
Mr = 896.79	Dx = 1.436 Mg m^−3
Triclinic, P1	Melting point: 153 K
a = 11.4603 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.6052 (13) Å	Cell parameters from 9916 reflections
c = 16.3587 (18) Å	θ = 2.3–31.1°
α = 92.862 (2)°	µ = 0.11 mm^−1
β = 105.149 (2)°	T = 90 K
γ = 97.497 (2)°	Block, colourless
V = 2074.1 (4) Å^3	0.71 × 0.62 × 0.49 mm
Z = 2

Data collection

Bruker APEXII CCD diffractometer	13178 independent reflections
Radiation source: fine-focus sealed tube	10248 reflections with I > 2σ(I)
Detector resolution: 512 pixels mm^-1	Rint = 0.035
φ and ω scans	θmax = 31.1°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2014)	h = −16→16
Tmin = 0.654, Tmax = 0.746	k = −16→16
39079 measured reflections	l = −23→23

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	All H-atom parameters refined
wR(F^2) = 0.144	w = 1/[σ^2(Fo^2) + (0.0653P)^2 + 1.4448P] where P = (Fo^2 + 2Fc^2)/3
S = 1.03	(Δ/σ)max = 0.001
13178 reflections	Δρmax = 0.48 e Å^−3
723 parameters	Δρmin = −0.28 e Å^−3
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.24608 (12)	0.39858 (12)	0.39427 (9)	0.0130 (2)
N1	0.31131 (10)	0.43400 (10)	0.33208 (7)	0.0130 (2)
O1	0.37537 (10)	0.49611 (10)	0.52499 (7)	0.0190 (2)
C4	0.28114 (12)	0.27649 (12)	0.42394 (9)	0.0140 (2)
O4	0.53906 (10)	0.37334 (10)	0.24205 (7)	0.0208 (2)
N4	0.29468 (11)	0.27230 (10)	0.23218 (7)	0.0133 (2)
C3	0.19691 (15)	0.58488 (15)	0.47717 (12)	0.0241 (3)
H3B	0.135 (2)	0.588 (2)	0.4250 (16)	0.041 (7)*
H3A	0.247 (2)	0.660 (2)	0.4924 (14)	0.031 (6)*
H3C	0.159 (3)	0.570 (2)	0.5222 (18)	0.052 (8)*
N3	0.37290 (10)	0.35171 (10)	0.29934 (8)	0.0136 (2)
O3	0.35598 (10)	0.63195 (9)	0.36913 (7)	0.0163 (2)
C2	0.28000 (13)	0.49659 (13)	0.47208 (9)	0.0158 (3)
N2	0.47231 (11)	0.53250 (10)	0.29990 (8)	0.0140 (2)
O2	0.20036 (10)	0.19420 (9)	0.40480 (7)	0.0187 (2)
C5	0.40888 (13)	0.26733 (14)	0.47423 (10)	0.0180 (3)
H5C	0.408 (2)	0.2675 (19)	0.5346 (15)	0.030 (6)*
H5B	0.4695 (19)	0.3310 (19)	0.4695 (13)	0.024 (5)*
H5A	0.431 (2)	0.193 (2)	0.4555 (14)	0.032 (6)*
N5	0.35635 (12)	0.14249 (11)	0.15121 (8)	0.0160 (2)
O5	0.37973 (10)	0.11364 (9)	0.29333 (7)	0.0186 (2)
C6	0.37786 (12)	0.54449 (12)	0.33755 (8)	0.0125 (2)
O6	0.28976 (11)	0.21950 (10)	0.02152 (7)	0.0213 (2)
N6	0.28172 (11)	0.31233 (11)	0.14880 (7)	0.0147 (2)
C7	0.56356 (13)	0.62976 (13)	0.29845 (9)	0.0160 (3)
N7	0.13708 (11)	0.43388 (10)	0.17176 (8)	0.0133 (2)
O7	0.09704 (11)	0.44105 (10)	−0.02179 (7)	0.0221 (2)
C8	0.52530 (15)	0.73599 (14)	0.27799 (10)	0.0199 (3)
H8	0.436 (2)	0.739 (2)	0.2593 (14)	0.032 (6)*
N8	0.06491 (11)	0.59341 (10)	0.20767 (8)	0.0144 (2)
O8	0.08330 (11)	0.15582 (9)	0.09693 (7)	0.0211 (2)
C9	0.61298 (17)	0.83326 (15)	0.28526 (11)	0.0250 (3)
H9	0.586 (2)	0.909 (2)	0.2718 (16)	0.039 (6)*
N9	0.03532 (11)	0.39687 (10)	0.20407 (8)	0.0145 (2)
O9	0.22320 (10)	0.61325 (9)	0.14225 (7)	0.0180 (2)
C10	0.73652 (17)	0.82374 (16)	0.31052 (11)	0.0278 (4)
H10	0.798 (2)	0.891 (2)	0.3163 (14)	0.032 (6)*
N10	0.06315 (11)	0.32378 (10)	0.27181 (7)	0.0132 (2)
O10	−0.08712 (10)	0.50155 (10)	0.26342 (8)	0.0221 (2)
C11	0.77312 (16)	0.71606 (17)	0.32720 (11)	0.0265 (3)
H11	0.859 (2)	0.7088 (19)	0.3431 (14)	0.030 (6)*
N11	−0.05242 (11)	0.25801 (11)	0.35741 (8)	0.0146 (2)
O11	−0.11892 (10)	0.19426 (10)	0.21348 (7)	0.0191 (2)
C12	0.68704 (14)	0.61756 (15)	0.32163 (10)	0.0200 (3)
H12	0.7112 (19)	0.5402 (19)	0.3330 (13)	0.024 (5)*
N12	0.11224 (10)	0.38634 (11)	0.35481 (8)	0.0136 (2)
O12	0.07152 (10)	0.35539 (10)	0.48427 (7)	0.0199 (2)
C13	0.47374 (13)	0.41727 (13)	0.27664 (9)	0.0147 (3)
C14	0.34883 (13)	0.16658 (12)	0.23253 (9)	0.0142 (2)
C15	0.40963 (13)	0.04569 (13)	0.12586 (9)	0.0162 (3)
C16	0.53077 (14)	0.06568 (15)	0.12328 (10)	0.0200 (3)
H16	0.5784 (19)	0.1423 (19)	0.1369 (13)	0.023 (5)*
C17	0.58237 (16)	−0.02754 (17)	0.09866 (11)	0.0253 (3)
H17	0.664 (2)	−0.015 (2)	0.0957 (14)	0.032 (6)*
C18	0.51398 (18)	−0.13774 (16)	0.07846 (11)	0.0263 (4)
H18	0.552 (2)	−0.2016 (19)	0.0600 (14)	0.029 (5)*
C19	0.39377 (18)	−0.15623 (15)	0.08272 (11)	0.0254 (3)
H19	0.346 (2)	−0.234 (2)	0.0691 (14)	0.032 (6)*
C20	0.34025 (15)	−0.06375 (14)	0.10626 (10)	0.0206 (3)
H20	0.257 (2)	−0.0734 (19)	0.1074 (14)	0.027 (5)*
C21	0.30814 (13)	0.22312 (13)	0.09749 (9)	0.0160 (3)
C22	0.16640 (13)	0.35719 (12)	0.10931 (9)	0.0142 (2)
C23	0.18716 (15)	0.42737 (13)	0.03221 (9)	0.0177 (3)
C24	0.31380 (17)	0.47431 (16)	0.02730 (12)	0.0246 (3)
H24B	0.371 (2)	0.484 (2)	0.0805 (16)	0.039 (6)*
H24A	0.311 (2)	0.551 (2)	0.0054 (15)	0.037 (6)*
H24C	0.339 (2)	0.424 (2)	−0.0108 (17)	0.045 (7)*
C25	0.05842 (14)	0.25055 (13)	0.07876 (9)	0.0164 (3)
C26	−0.06640 (15)	0.26985 (15)	0.02957 (10)	0.0213 (3)
H26C	−0.075 (2)	0.250 (2)	−0.0277 (15)	0.032 (6)*
H26A	−0.125 (2)	0.217 (2)	0.0483 (14)	0.030 (6)*
H26B	−0.079 (2)	0.351 (2)	0.0376 (15)	0.034 (6)*
C27	0.15076 (13)	0.55470 (12)	0.17043 (8)	0.0135 (2)
C28	0.05292 (14)	0.71531 (12)	0.21756 (9)	0.0166 (3)
C29	0.15085 (16)	0.79129 (14)	0.26863 (11)	0.0228 (3)
H29	0.224 (2)	0.7626 (19)	0.3002 (14)	0.029 (5)*
C30	0.14256 (19)	0.91030 (15)	0.27420 (13)	0.0295 (4)
H30	0.211 (2)	0.963 (2)	0.3068 (16)	0.042 (7)*
C31	0.0379 (2)	0.95040 (15)	0.22947 (13)	0.0324 (4)
H31	0.037 (2)	1.033 (2)	0.2318 (16)	0.046 (7)*
C32	−0.0603 (2)	0.87235 (17)	0.18003 (12)	0.0326 (4)
H32	−0.131 (2)	0.899 (2)	0.1495 (16)	0.039 (6)*
C33	−0.05403 (16)	0.75345 (15)	0.17386 (10)	0.0234 (3)
H33	−0.118 (2)	0.6981 (19)	0.1422 (14)	0.026 (5)*
C34	−0.00721 (13)	0.50172 (13)	0.22881 (9)	0.0158 (3)
C35	−0.04846 (12)	0.25021 (12)	0.27377 (9)	0.0138 (2)
C36	−0.13569 (12)	0.18572 (12)	0.39226 (9)	0.0150 (3)
C37	−0.26087 (13)	0.17956 (14)	0.35755 (10)	0.0194 (3)
H37	−0.2920 (19)	0.2238 (18)	0.3088 (13)	0.024 (5)*
C38	−0.33902 (15)	0.11269 (16)	0.39501 (12)	0.0275 (4)
H38	−0.423 (2)	0.106 (2)	0.3730 (15)	0.036 (6)*
C39	−0.29274 (17)	0.05439 (16)	0.46554 (13)	0.0299 (4)
H39	−0.352 (2)	0.011 (2)	0.4934 (17)	0.048 (7)*
C40	−0.16729 (17)	0.06081 (15)	0.49883 (12)	0.0267 (3)
H40	−0.136 (2)	0.020 (2)	0.5486 (15)	0.032 (6)*
C41	−0.08785 (14)	0.12622 (14)	0.46216 (10)	0.0204 (3)
H41	−0.0021 (19)	0.1302 (18)	0.4844 (13)	0.024 (5)*
C42	0.04521 (12)	0.33534 (13)	0.40814 (9)	0.0149 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0110 (5)	0.0135 (6)	0.0132 (6)	0.0005 (5)	0.0022 (5)	−0.0014 (5)
N1	0.0137 (5)	0.0111 (5)	0.0139 (5)	0.0022 (4)	0.0040 (4)	−0.0026 (4)
O1	0.0214 (5)	0.0195 (5)	0.0127 (5)	−0.0031 (4)	0.0022 (4)	−0.0017 (4)
C4	0.0148 (6)	0.0152 (6)	0.0117 (6)	0.0027 (5)	0.0030 (5)	−0.0003 (5)
O4	0.0185 (5)	0.0218 (5)	0.0240 (5)	0.0056 (4)	0.0085 (4)	−0.0020 (4)
N4	0.0163 (5)	0.0115 (5)	0.0109 (5)	0.0046 (4)	0.0007 (4)	−0.0012 (4)
C3	0.0207 (7)	0.0190 (7)	0.0323 (9)	−0.0004 (6)	0.0104 (7)	−0.0107 (6)
N3	0.0134 (5)	0.0119 (5)	0.0148 (5)	0.0030 (4)	0.0031 (4)	−0.0036 (4)
O3	0.0201 (5)	0.0130 (5)	0.0154 (5)	0.0041 (4)	0.0037 (4)	−0.0008 (4)
C2	0.0179 (6)	0.0140 (6)	0.0153 (6)	−0.0019 (5)	0.0069 (5)	−0.0036 (5)
N2	0.0146 (5)	0.0124 (5)	0.0149 (5)	0.0020 (4)	0.0042 (4)	0.0008 (4)
O2	0.0171 (5)	0.0152 (5)	0.0219 (5)	0.0004 (4)	0.0027 (4)	0.0014 (4)
C5	0.0155 (6)	0.0206 (7)	0.0161 (7)	0.0035 (5)	0.0006 (5)	0.0006 (5)
N5	0.0218 (6)	0.0136 (5)	0.0134 (5)	0.0091 (5)	0.0033 (4)	−0.0005 (4)
O5	0.0227 (5)	0.0164 (5)	0.0160 (5)	0.0061 (4)	0.0023 (4)	0.0019 (4)
C6	0.0126 (5)	0.0132 (6)	0.0103 (6)	0.0023 (5)	0.0004 (4)	0.0016 (5)
O6	0.0291 (6)	0.0237 (6)	0.0131 (5)	0.0115 (5)	0.0059 (4)	0.0008 (4)
N6	0.0176 (5)	0.0154 (6)	0.0115 (5)	0.0071 (4)	0.0025 (4)	0.0011 (4)
C7	0.0188 (6)	0.0164 (6)	0.0122 (6)	−0.0016 (5)	0.0051 (5)	0.0004 (5)
N7	0.0160 (5)	0.0112 (5)	0.0140 (5)	0.0044 (4)	0.0049 (4)	0.0015 (4)
O7	0.0326 (6)	0.0198 (5)	0.0146 (5)	0.0096 (5)	0.0044 (4)	0.0035 (4)
C8	0.0251 (7)	0.0187 (7)	0.0146 (6)	0.0012 (6)	0.0039 (6)	0.0036 (5)
N8	0.0179 (5)	0.0109 (5)	0.0148 (5)	0.0058 (4)	0.0033 (4)	0.0003 (4)
O8	0.0264 (6)	0.0135 (5)	0.0215 (5)	0.0047 (4)	0.0027 (4)	0.0003 (4)
C9	0.0372 (9)	0.0179 (7)	0.0191 (7)	−0.0020 (6)	0.0087 (7)	0.0028 (6)
N9	0.0163 (5)	0.0123 (5)	0.0164 (6)	0.0062 (4)	0.0047 (4)	0.0035 (4)
O9	0.0224 (5)	0.0147 (5)	0.0171 (5)	0.0029 (4)	0.0057 (4)	0.0021 (4)
C10	0.0338 (9)	0.0243 (8)	0.0234 (8)	−0.0099 (7)	0.0119 (7)	−0.0003 (6)
N10	0.0146 (5)	0.0120 (5)	0.0110 (5)	0.0017 (4)	0.0005 (4)	0.0002 (4)
O10	0.0202 (5)	0.0200 (5)	0.0304 (6)	0.0082 (4)	0.0114 (5)	0.0039 (5)
C11	0.0214 (7)	0.0324 (9)	0.0251 (8)	−0.0039 (6)	0.0094 (6)	0.0004 (7)
N11	0.0129 (5)	0.0147 (5)	0.0149 (5)	0.0006 (4)	0.0024 (4)	−0.0004 (4)
O11	0.0187 (5)	0.0177 (5)	0.0172 (5)	0.0000 (4)	0.0004 (4)	−0.0022 (4)
C12	0.0189 (7)	0.0232 (8)	0.0191 (7)	0.0011 (6)	0.0081 (6)	0.0019 (6)
N12	0.0120 (5)	0.0145 (5)	0.0129 (5)	0.0017 (4)	0.0018 (4)	−0.0027 (4)
O12	0.0175 (5)	0.0251 (6)	0.0155 (5)	−0.0008 (4)	0.0041 (4)	−0.0032 (4)
C13	0.0148 (6)	0.0147 (6)	0.0138 (6)	0.0036 (5)	0.0018 (5)	0.0000 (5)
C14	0.0150 (6)	0.0116 (6)	0.0149 (6)	0.0032 (5)	0.0022 (5)	−0.0022 (5)
C15	0.0208 (6)	0.0153 (6)	0.0137 (6)	0.0100 (5)	0.0036 (5)	0.0006 (5)
C16	0.0201 (7)	0.0229 (8)	0.0184 (7)	0.0078 (6)	0.0050 (6)	0.0035 (6)
C17	0.0251 (8)	0.0350 (9)	0.0225 (8)	0.0178 (7)	0.0103 (6)	0.0089 (7)
C18	0.0415 (9)	0.0260 (8)	0.0202 (7)	0.0234 (7)	0.0137 (7)	0.0067 (6)
C19	0.0385 (9)	0.0166 (7)	0.0230 (8)	0.0093 (7)	0.0093 (7)	0.0000 (6)
C20	0.0235 (7)	0.0178 (7)	0.0210 (7)	0.0052 (6)	0.0063 (6)	−0.0010 (6)
C21	0.0183 (6)	0.0146 (6)	0.0160 (6)	0.0068 (5)	0.0044 (5)	0.0008 (5)
C22	0.0179 (6)	0.0126 (6)	0.0123 (6)	0.0062 (5)	0.0024 (5)	0.0011 (5)
C23	0.0281 (7)	0.0125 (6)	0.0157 (6)	0.0073 (5)	0.0091 (6)	0.0014 (5)
C24	0.0292 (8)	0.0220 (8)	0.0281 (8)	0.0076 (6)	0.0149 (7)	0.0060 (7)
C25	0.0211 (6)	0.0145 (6)	0.0125 (6)	0.0040 (5)	0.0024 (5)	0.0004 (5)
C26	0.0202 (7)	0.0218 (8)	0.0177 (7)	0.0033 (6)	−0.0021 (6)	0.0024 (6)
C27	0.0167 (6)	0.0123 (6)	0.0098 (6)	0.0048 (5)	−0.0004 (5)	0.0005 (5)
C28	0.0252 (7)	0.0120 (6)	0.0159 (6)	0.0088 (5)	0.0081 (5)	0.0035 (5)
C29	0.0259 (8)	0.0154 (7)	0.0273 (8)	0.0055 (6)	0.0064 (6)	0.0011 (6)
C30	0.0412 (10)	0.0146 (7)	0.0371 (10)	0.0035 (7)	0.0188 (8)	0.0009 (7)
C31	0.0574 (12)	0.0152 (7)	0.0370 (10)	0.0179 (8)	0.0272 (9)	0.0097 (7)
C32	0.0492 (11)	0.0293 (9)	0.0287 (9)	0.0288 (9)	0.0144 (8)	0.0101 (7)
C33	0.0302 (8)	0.0229 (8)	0.0190 (7)	0.0154 (7)	0.0046 (6)	0.0011 (6)
C34	0.0159 (6)	0.0144 (6)	0.0163 (6)	0.0059 (5)	0.0014 (5)	0.0011 (5)
C35	0.0134 (6)	0.0117 (6)	0.0156 (6)	0.0035 (5)	0.0022 (5)	0.0011 (5)
C36	0.0127 (6)	0.0137 (6)	0.0184 (6)	0.0005 (5)	0.0051 (5)	−0.0011 (5)
C37	0.0141 (6)	0.0198 (7)	0.0216 (7)	0.0017 (5)	0.0014 (5)	−0.0041 (6)
C38	0.0148 (7)	0.0294 (9)	0.0361 (9)	−0.0034 (6)	0.0082 (6)	−0.0076 (7)
C39	0.0294 (9)	0.0253 (8)	0.0373 (10)	−0.0057 (7)	0.0191 (8)	−0.0028 (7)
C40	0.0328 (9)	0.0216 (8)	0.0284 (8)	0.0026 (7)	0.0130 (7)	0.0063 (7)
C41	0.0185 (7)	0.0212 (7)	0.0219 (7)	0.0044 (6)	0.0050 (6)	0.0047 (6)
C42	0.0126 (6)	0.0150 (6)	0.0169 (6)	0.0025 (5)	0.0038 (5)	−0.0005 (5)

Geometric parameters (Å, º)

C1—N1	1.4567 (18)	O10—C34	1.1957 (18)
C1—N12	1.4853 (17)	C11—C12	1.392 (2)
C1—C4	1.587 (2)	C11—H11	0.968
C1—C2	1.5958 (19)	C12—H12	0.986
N1—C6	1.3898 (18)	N11—C35	1.3797 (18)
N1—N3	1.4211 (15)	N11—C42	1.3871 (18)
O1—C2	1.2047 (18)	N11—C36	1.4362 (18)
C4—O2	1.2063 (18)	O11—C35	1.1956 (17)
C4—C5	1.500 (2)	N12—C42	1.4087 (18)
C5—H5A	0.986	O12—C42	1.2052 (18)
C5—H5B	0.967	C15—C20	1.382 (2)
C5—H5C	0.989	C15—C16	1.389 (2)
O4—C13	1.1970 (17)	C16—C17	1.389 (2)
N4—N3	1.4243 (16)	C16—H16	0.964
N4—N6	1.4400 (17)	C17—C18	1.386 (3)
N4—C14	1.4450 (17)	C17—H17	0.947
C3—C2	1.500 (2)	C18—C19	1.387 (3)
C3—H3A	0.965	C18—H18	0.977
C3—H3B	0.963	C19—C20	1.389 (2)
C3—H3C	0.960	C19—H19	0.975
N3—C13	1.4407 (18)	C20—H20	0.952
O3—C6	1.2007 (17)	C22—C23	1.587 (2)
N2—C13	1.3753 (18)	C22—C25	1.590 (2)
N2—C6	1.3964 (18)	C23—C24	1.506 (2)
N2—C7	1.4407 (19)	C24—H24A	0.978
N5—C14	1.3727 (18)	C24—H24B	0.933
N5—C21	1.3843 (18)	C24—H24C	0.951
N5—C15	1.4393 (17)	C25—C26	1.498 (2)
O5—C14	1.1942 (18)	C26—H26A	0.969
O6—C21	1.2027 (18)	C26—H26B	0.982
N6—C21	1.4127 (18)	C26—H26C	0.931
N6—C22	1.4839 (18)	C28—C29	1.383 (2)
C7—C8	1.389 (2)	C28—C33	1.387 (2)
C7—C12	1.394 (2)	C29—C30	1.397 (2)
C8—H8	0.990	C29—H29	0.968
N7—C27	1.3923 (18)	C30—C31	1.383 (3)
N7—N9	1.4276 (17)	C30—H30	0.947
N7—C22	1.4544 (18)	C31—C32	1.387 (3)
O7—C23	1.2050 (19)	C31—H31	0.962
C8—C9	1.388 (2)	C32—C33	1.391 (2)
C9—H9	0.981	C32—H32	0.937
N8—C34	1.3754 (19)	C33—H33	0.930
N8—C27	1.3936 (18)	C36—C37	1.389 (2)
N8—C28	1.4443 (18)	C36—C41	1.391 (2)
O8—C25	1.2034 (18)	C37—C38	1.390 (2)
C9—C10	1.388 (3)	C37—H37	0.983
N9—N10	1.4244 (16)	C38—C39	1.386 (3)
N9—C34	1.4460 (18)	C38—H38	0.927
O9—C27	1.2032 (18)	C39—C40	1.389 (3)
C10—C11	1.387 (3)	C39—H39	1.012
C10—H10	0.965	C40—C41	1.384 (2)
N10—N12	1.4432 (16)	C40—H40	0.974
N10—C35	1.4509 (18)
N1—C1—N12	109.66 (11)	C16—C15—N5	118.34 (14)
N1—C1—C4	108.38 (10)	C17—C16—C15	118.46 (16)
N12—C1—C4	109.43 (11)	C15—C16—H16	121.64
N1—C1—C2	109.67 (11)	C17—C16—H16	119.88
N12—C1—C2	107.77 (11)	C18—C17—C16	120.13 (16)
C4—C1—C2	111.92 (11)	C16—C17—H17	119.17
C6—N1—N3	108.56 (11)	C18—C17—H17	120.70
C6—N1—C1	122.53 (11)	C17—C18—C19	120.51 (15)
N3—N1—C1	118.57 (11)	C17—C18—H18	118.67
O2—C4—C5	122.98 (13)	C19—C18—H18	120.81
O2—C4—C1	116.67 (12)	C18—C19—C20	120.14 (16)
C5—C4—C1	120.34 (12)	C18—C19—H19	120.50
C4—C5—H5A	108.50	C20—C19—H19	119.36
C4—C5—H5B	114.14	C15—C20—C19	118.59 (15)
C4—C5—H5C	106.79	C15—C20—H20	119.53
H5A—C5—H5B	109.62	C19—C20—H20	121.85
H5A—C5—H5C	109.72	O6—C21—N5	127.80 (13)
H5B—C5—H5C	108.00	O6—C21—N6	125.31 (13)
N3—N4—N6	114.20 (11)	N5—C21—N6	106.88 (12)
N3—N4—C14	107.29 (10)	N7—C22—N6	109.55 (11)
N6—N4—C14	106.58 (10)	N7—C22—C23	110.15 (11)
N1—N3—N4	113.56 (10)	N6—C22—C23	107.60 (11)
N1—N3—C13	106.89 (11)	N7—C22—C25	108.53 (11)
N4—N3—C13	113.91 (11)	N6—C22—C25	109.21 (11)
O1—C2—C3	122.61 (14)	C23—C22—C25	111.78 (11)
O1—C2—C1	116.51 (13)	O7—C23—C24	121.94 (14)
C3—C2—C1	120.88 (13)	C23—C24—H24A	108.02
C2—C3—H3A	107.27	C23—C24—H24B	112.17
C2—C3—H3B	114.25	C23—C24—H24C	110.27
C2—C3—H3C	110.24	H24A—C24—H24B	107.78
H3A—C3—H3B	108.73	H24A—C24—H24C	108.58
H3A—C3—H3C	106.70	H24B—C24—H24C	109.91
H3B—C3—H3C	109.35	O7—C23—C22	116.81 (14)
C13—N2—C6	111.18 (12)	C24—C23—C22	121.24 (13)
C13—N2—C7	126.53 (12)	O8—C25—C26	123.05 (14)
C6—N2—C7	121.75 (12)	O8—C25—C22	116.44 (13)
C14—N5—C21	111.83 (12)	C26—C25—C22	120.51 (12)
C14—N5—C15	123.64 (12)	C25—C26—H26A	107.06
C21—N5—C15	124.52 (12)	C25—C26—H26B	111.70
O3—C6—N1	125.23 (13)	C25—C26—H26C	108.15
O3—C6—N2	127.93 (13)	H26A—C26—H26B	111.70
N1—C6—N2	106.84 (11)	H26A—C26—H26C	108.42
C21—N6—N4	107.30 (11)	H26B—C26—H26C	109.68
C21—N6—C22	113.81 (11)	O9—C27—N7	125.96 (13)
N4—N6—C22	116.81 (11)	O9—C27—N8	127.25 (13)
C8—C7—C12	121.64 (14)	N7—C27—N8	106.79 (12)
C8—C7—N2	118.22 (13)	C29—C28—C33	121.98 (14)
C12—C7—N2	120.05 (13)	C29—C28—N8	118.50 (13)
C27—N7—N9	108.79 (11)	C33—C28—N8	119.49 (14)
C27—N7—C22	122.97 (12)	C28—C29—C30	118.72 (16)
N9—N7—C22	119.50 (11)	C28—C29—H29	120.72
C9—C8—C7	118.75 (15)	C30—C29—H29	120.56
C7—C8—H8	118.10	C31—C30—C29	120.17 (18)
C9—C8—H8	123.15	C29—C30—H30	119.31
C34—N8—C27	111.51 (11)	C31—C30—H30	120.46
C34—N8—C28	126.11 (12)	C30—C31—C32	120.13 (16)
C27—N8—C28	122.31 (12)	C30—C31—H31	118.08
C8—C9—C10	120.51 (16)	C32—C31—H31	121.73
C8—C9—H9	119.04	C31—C32—C33	120.59 (17)
C10—C9—H9	120.45	C31—C32—H32	120.21
N10—N9—N7	113.37 (10)	C33—C32—H32	119.18
N10—N9—C34	112.45 (11)	C28—C33—C32	118.37 (17)
N7—N9—C34	106.46 (11)	C28—C33—H33	118.32
C11—C10—C9	120.00 (16)	C32—C33—H33	123.30
C9—C10—H10	120.56	O10—C34—N8	130.25 (14)
C11—C10—H10	119.44	O10—C34—N9	123.45 (14)
N9—N10—N12	114.16 (11)	N8—C34—N9	106.25 (12)
N9—N10—C35	108.69 (10)	O11—C35—N11	129.09 (14)
N12—N10—C35	106.83 (10)	O11—C35—N10	124.93 (13)
C10—C11—C12	120.58 (16)	N11—C35—N10	105.97 (11)
C10—C11—H11	120.12	C37—C36—C41	121.73 (14)
C12—C11—H11	119.30	C37—C36—N11	119.75 (13)
C35—N11—C42	111.54 (12)	C41—C36—N11	118.49 (13)
C35—N11—C36	125.71 (12)	C36—C37—C38	118.31 (16)
C42—N11—C36	122.28 (12)	C36—C37—H37	119.92
C11—C12—C7	118.43 (16)	C38—C37—H37	121.75
C7—C12—H12	119.76	C39—C38—C37	120.65 (16)
C11—C12—H12	121.81	C37—C38—H38	120.50
C42—N12—N10	106.92 (11)	C39—C38—C37	118.85
C42—N12—C1	111.71 (11)	C38—C39—C40	120.16 (16)
N10—N12—C1	118.25 (10)	C38—C39—H39	118.40
O4—C13—N2	130.56 (14)	C40—C39—H39	121.38
O4—C13—N3	123.25 (13)	C41—C40—C39	120.15 (17)
N2—C13—N3	106.15 (11)	C39—C40—H40	119.31
O5—C14—N5	128.81 (13)	C41—C40—H40	120.54
O5—C14—N4	124.81 (13)	C40—C41—C36	119.00 (15)
N5—C14—N4	106.38 (12)	O12—C42—N11	127.40 (14)
C20—C15—C16	122.16 (14)	O12—C42—N12	124.91 (13)
C20—C15—N5	119.50 (13)	N11—C42—N12	107.68 (12)
N12—C1—N1—C6	109.95 (13)	C17—C18—C19—C20	0.9 (3)
C4—C1—N1—C6	−130.65 (12)	C16—C15—C20—C19	−0.4 (2)
C2—C1—N1—C6	−8.20 (17)	N5—C15—C20—C19	−179.39 (14)
N12—C1—N1—N3	−109.05 (13)	C18—C19—C20—C15	−0.6 (2)
C4—C1—N1—N3	10.35 (15)	C14—N5—C21—O6	−171.63 (16)
C2—C1—N1—N3	132.80 (12)	C15—N5—C21—O6	9.2 (3)
N1—C1—C4—O2	−113.81 (14)	C14—N5—C21—N6	7.49 (17)
N12—C1—C4—O2	5.74 (17)	C15—N5—C21—N6	−171.72 (13)
C2—C1—C4—O2	125.13 (13)	N4—N6—C21—O6	168.88 (15)
N1—C1—C4—C5	66.98 (15)	C22—N6—C21—O6	38.1 (2)
N12—C1—C4—C5	−173.47 (12)	N4—N6—C21—N5	−10.27 (15)
C2—C1—C4—C5	−54.08 (16)	C22—N6—C21—N5	−141.09 (12)
C6—N1—N3—N4	−132.21 (12)	C27—N7—C22—N6	106.23 (14)
C1—N1—N3—N4	81.82 (14)	N9—N7—C22—N6	−109.87 (13)
C6—N1—N3—C13	−5.74 (14)	C27—N7—C22—C23	−11.94 (18)
C1—N1—N3—C13	−151.71 (11)	N9—N7—C22—C23	131.96 (12)
N6—N4—N3—N1	88.78 (13)	C27—N7—C22—C25	−134.61 (13)
C14—N4—N3—N1	−153.35 (11)	N9—N7—C22—C25	9.29 (16)
N6—N4—N3—C13	−33.90 (15)	C21—N6—C22—N7	170.67 (12)
C14—N4—N3—C13	83.96 (13)	N4—N6—C22—N7	44.72 (16)
N1—C1—C2—O1	−80.54 (16)	C21—N6—C22—C23	−69.58 (15)
N12—C1—C2—O1	160.14 (13)	N4—N6—C22—C23	164.47 (11)
C4—C1—C2—O1	39.78 (17)	C21—N6—C22—C25	51.93 (15)
N1—C1—C2—C3	98.66 (15)	N4—N6—C22—C25	−74.02 (14)
N12—C1—C2—C3	−20.66 (18)	N7—C22—C23—O7	−81.60 (16)
C4—C1—C2—C3	−141.03 (14)	N6—C22—C23—O7	159.04 (13)
N3—N1—C6—O3	−173.61 (13)	C25—C22—C23—O7	39.15 (17)
C1—N1—C6—O3	−29.3 (2)	N7—C22—C23—C24	98.40 (15)
N3—N1—C6—N2	6.34 (14)	N6—C22—C23—C24	−20.97 (18)
C1—N1—C6—N2	150.68 (12)	C25—C22—C23—C24	−140.86 (14)
C13—N2—C6—O3	175.31 (14)	N7—C22—C25—O8	−114.30 (14)
C7—N2—C6—O3	3.3 (2)	N6—C22—C25—O8	5.07 (17)
C13—N2—C6—N1	−4.64 (15)	C23—C22—C25—O8	124.02 (14)
C7—N2—C6—N1	−176.68 (12)	N7—C22—C25—C26	66.11 (16)
N3—N4—N6—C21	127.63 (12)	N6—C22—C25—C26	−174.52 (13)
C14—N4—N6—C21	9.36 (14)	C23—C22—C25—C26	−55.58 (17)
N3—N4—N6—C22	−103.24 (13)	N9—N7—C27—O9	−175.40 (13)
C14—N4—N6—C22	138.49 (12)	C22—N7—C27—O9	−28.2 (2)
C13—N2—C7—C8	145.21 (14)	N9—N7—C27—N8	4.56 (14)
C6—N2—C7—C8	−44.03 (19)	C22—N7—C27—N8	151.76 (12)
C13—N2—C7—C12	−38.2 (2)	C34—N8—C27—O9	176.88 (14)
C6—N2—C7—C12	132.58 (14)	C28—N8—C27—O9	−0.3 (2)
C12—C7—C8—C9	−3.4 (2)	C34—N8—C27—N7	−3.08 (15)
N2—C7—C8—C9	173.14 (14)	C28—N8—C27—N7	179.74 (12)
C7—C8—C9—C10	1.6 (2)	C34—N8—C28—C29	120.37 (16)
C27—N7—N9—N10	−128.51 (12)	C27—N8—C28—C29	−62.87 (19)
C22—N7—N9—N10	82.96 (14)	C34—N8—C28—C33	−61.7 (2)
C27—N7—N9—C34	−4.36 (14)	C27—N8—C28—C33	115.09 (16)
C22—N7—N9—C34	−152.88 (12)	C33—C28—C29—C30	−1.8 (2)
C8—C9—C10—C11	1.2 (3)	N8—C28—C29—C30	176.06 (15)
N7—N9—N10—N12	86.78 (13)	C28—C29—C30—C31	0.2 (3)
C34—N9—N10—N12	−34.05 (15)	C29—C30—C31—C32	1.1 (3)
N7—N9—N10—C35	−154.09 (11)	C30—C31—C32—C33	−0.9 (3)
C34—N9—N10—C35	85.08 (13)	C29—C28—C33—C32	2.1 (2)
C9—C10—C11—C12	−2.2 (3)	N8—C28—C33—C32	−175.83 (15)
C10—C11—C12—C7	0.4 (2)	C31—C32—C33—C28	−0.6 (3)
C8—C7—C12—C11	2.5 (2)	C27—N8—C34—O10	177.74 (15)
N2—C7—C12—C11	−174.04 (14)	C28—N8—C34—O10	−5.2 (2)
N9—N10—N12—C42	130.77 (12)	C27—N8—C34—N9	0.36 (15)
C35—N10—N12—C42	10.59 (13)	C28—N8—C34—N9	177.42 (12)
N9—N10—N12—C1	−102.20 (13)	N10—N9—C34—O10	−50.45 (19)
C35—N10—N12—C1	137.63 (12)	N7—N9—C34—O10	−175.18 (14)
N1—C1—N12—C42	171.01 (11)	N10—N9—C34—N8	127.15 (12)
C4—C1—N12—C42	52.26 (14)	N7—N9—C34—N8	2.42 (14)
C2—C1—N12—C42	−69.66 (14)	C42—N11—C35—O11	−178.26 (14)
N1—C1—N12—N10	46.30 (15)	C36—N11—C35—O11	9.6 (2)
C4—C1—N12—N10	−72.45 (14)	C42—N11—C35—N10	2.88 (15)
C2—C1—N12—N10	165.63 (11)	C36—N11—C35—N10	−169.29 (12)
C6—N2—C13—O4	178.80 (15)	N9—N10—C35—O11	49.19 (18)
C7—N2—C13—O4	−9.6 (2)	N12—N10—C35—O11	172.81 (13)
C6—N2—C13—N3	1.06 (15)	N9—N10—C35—N11	−131.89 (11)
C7—N2—C13—N3	172.64 (12)	N12—N10—C35—N11	−8.26 (14)
N1—N3—C13—O4	−175.09 (13)	C35—N11—C36—C37	−56.6 (2)
N4—N3—C13—O4	−48.83 (18)	C42—N11—C36—C37	131.99 (15)
N1—N3—C13—N2	2.85 (14)	C35—N11—C36—C41	125.31 (16)
N4—N3—C13—N2	129.11 (12)	C42—N11—C36—C41	−46.07 (19)
C21—N5—C14—O5	178.54 (15)	C41—C36—C37—C38	0.7 (2)
C15—N5—C14—O5	−2.2 (2)	N11—C36—C37—C38	−177.33 (14)
C21—N5—C14—N4	−1.57 (16)	C36—C37—C38—C39	0.4 (2)
C15—N5—C14—N4	177.66 (13)	C37—C38—C39—C40	−1.0 (3)
N3—N4—C14—O5	52.31 (18)	C38—C39—C40—C41	0.5 (3)
N6—N4—C14—O5	175.04 (14)	C39—C40—C41—C36	0.5 (3)
N3—N4—C14—N5	−127.59 (12)	C37—C36—C41—C40	−1.1 (2)
N6—N4—C14—N5	−4.86 (15)	N11—C36—C41—C40	176.90 (14)
C14—N5—C15—C20	82.60 (19)	C35—N11—C42—O12	−174.88 (14)
C21—N5—C15—C20	−98.28 (18)	C36—N11—C42—O12	−2.4 (2)
C14—N5—C15—C16	−96.40 (18)	C35—N11—C42—N12	3.81 (16)
C21—N5—C15—C16	82.73 (19)	C36—N11—C42—N12	176.29 (12)
C20—C15—C16—C17	1.2 (2)	N10—N12—C42—O12	169.82 (14)
N5—C15—C16—C17	−179.87 (13)	C1—N12—C42—O12	39.01 (19)
C15—C16—C17—C18	−0.9 (2)	N10—N12—C42—N11	−8.91 (14)
C16—C17—C18—C19	−0.1 (3)	C1—N12—C42—N11	−139.72 (11)