2,4,6,8,10,12-Hexa­benzyl-5-(nitro­methyl­ene)-2,4,6,8,10,12-hexa­aza­tri­cyclo[7.3.0.0^3,7]­do­decane

The title compound, C₄₉H₄₉N₇O₂, is a crowded tricyclic heterocycle substituted with six benzyl groups. It is related to the hexa­aza­isowurtzitane family of high-density, high-energy polycyclic cage compounds. The central six-membered ring adopts a boat conformation which minimizes the steric repulsion of the six benzyl substituents. The nitro­methyl­ene substituent on the methyl­ene C atom of one of the five-membered rings has a considerable influence on the metric parameters of that ring. From the bond distances in the nitro group and the five-membered ring it appears that the mol­ecule is zwitterionic, rather than neutral, in the vicinity of the nitro group.

Key indicators

• Single-crystal X-ray study
• T = 93 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.059
• wR factor = 0.116
• Data-to-parameter ratio = 15.5

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS (Sheldrick, 1990); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

2,4,6,8,10,12-hexaaza-2,4,6,8,10,12-hexabenzyl-5-(nitromethylene)- tricyclo[7.3.0.0^3,7]dodecane

Crystal data

C49H49N7O2	Z = 2
Mr = 767.95	F(000) = 816
Triclinic, P1	Dx = 1.273 Mg m^−3
a = 10.4199 (15) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.7594 (17) Å	Cell parameters from 7939 reflections
c = 17.288 (3) Å	θ = 2.3–28.3°
α = 71.449 (2)°	µ = 0.08 mm^−1
β = 86.811 (3)°	T = 93 K
γ = 86.953 (3)°	Slab, colorless
V = 2003.7 (5) Å^3	0.52 × 0.26 × 0.1 mm

Data collection

Bruker CCD area-detector diffractometer	8141 independent reflections
Radiation source: fine-focus sealed tube	5974 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
φ and ω scans	θmax = 26.4°, θmin = 1.8°
Absorption correction: integration (Wuensch & Prewitt, 1965)	h = −13→12
Tmin = 0.976, Tmax = 0.992	k = −14→14
13583 measured reflections	l = −21→21

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)] = 0.059	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.0381P)^2 + 0.7713P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
8141 reflections	Δρmax = 0.29 e Å^−3
524 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0031 (7)

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	0.07846 (17)	0.87037 (18)	0.32764 (12)	0.0166 (4)
H1A	−0.0130	0.8560	0.3478	0.020*
N2	0.11152 (14)	0.98495 (14)	0.33220 (10)	0.0159 (4)
C2	0.03141 (18)	1.04634 (18)	0.38047 (12)	0.0184 (4)
H2A	0.0880	1.0772	0.4128	0.022*
H2B	−0.0250	0.9873	0.4193	0.022*
C21	−0.05121 (18)	1.14930 (18)	0.32937 (12)	0.0181 (4)
C22	−0.01858 (19)	1.2677 (2)	0.31306 (14)	0.0259 (5)
H22A	0.0552	1.2853	0.3365	0.031*
C23	−0.0927 (2)	1.3609 (2)	0.26268 (15)	0.0320 (6)
H23A	−0.0693	1.4417	0.2516	0.038*
C24	−0.2003 (2)	1.3361 (2)	0.22873 (15)	0.0311 (6)
H24A	−0.2504	1.3998	0.1939	0.037*
C25	−0.23536 (19)	1.2188 (2)	0.24532 (14)	0.0258 (5)
H25A	−0.3102	1.2019	0.2226	0.031*
C26	−0.16127 (18)	1.12594 (19)	0.29508 (12)	0.0193 (4)
H26A	−0.1855	1.0454	0.3061	0.023*
C3	0.21886 (17)	1.04426 (17)	0.28471 (12)	0.0151 (4)
H3A	0.2084	1.1318	0.2781	0.018*
N4	0.34714 (14)	1.00024 (15)	0.31852 (10)	0.0161 (4)
C4	0.36589 (18)	0.97783 (19)	0.40507 (12)	0.0189 (4)
H4A	0.4538	0.9434	0.4182	0.023*
H4B	0.3040	0.9183	0.4377	0.023*
C41	0.34742 (17)	1.09124 (19)	0.42822 (12)	0.0192 (4)
C42	0.29983 (17)	1.0859 (2)	0.50641 (12)	0.0200 (5)
H42A	0.2841	1.0101	0.5459	0.024*
C43	0.27525 (19)	1.1899 (2)	0.52712 (13)	0.0243 (5)
H43A	0.2442	1.1850	0.5808	0.029*
C44	0.2959 (2)	1.3012 (2)	0.46967 (14)	0.0296 (5)
H44A	0.2775	1.3725	0.4836	0.036*
C45	0.3435 (2)	1.3080 (2)	0.39179 (14)	0.0318 (6)
H45A	0.3570	1.3841	0.3521	0.038*
C46	0.3714 (2)	1.2037 (2)	0.37186 (14)	0.0266 (5)
H46A	0.4074	1.2090	0.3192	0.032*
C5	0.42571 (17)	0.96268 (17)	0.26582 (12)	0.0146 (4)
C51	0.55712 (17)	0.93415 (18)	0.28394 (12)	0.0178 (4)
H51A	0.5914	0.9684	0.3209	0.021*
N5	0.63890 (15)	0.86301 (15)	0.25396 (10)	0.0172 (4)
O5A	0.75815 (12)	0.86205 (13)	0.26695 (9)	0.0209 (3)
O5B	0.59942 (12)	0.79802 (12)	0.21553 (9)	0.0204 (3)
N6	0.36426 (14)	0.97051 (14)	0.19785 (10)	0.0141 (4)
C6	0.42272 (18)	0.97700 (18)	0.11676 (12)	0.0168 (4)
H6A	0.3538	0.9765	0.0797	0.020*
H6B	0.4796	0.9050	0.1221	0.020*
C61	0.49980 (18)	1.08804 (18)	0.07952 (12)	0.0171 (4)
C62	0.43964 (19)	1.19971 (19)	0.04229 (12)	0.0231 (5)
H62A	0.3489	1.2053	0.0379	0.028*
C63	0.5097 (2)	1.3022 (2)	0.01178 (13)	0.0290 (5)
H63A	0.4668	1.3775	−0.0123	0.035*
C64	0.6419 (2)	1.2955 (2)	0.01622 (14)	0.0313 (5)
H64A	0.6900	1.3661	−0.0041	0.038*
C65	0.7037 (2)	1.1858 (2)	0.05037 (14)	0.0311 (6)
H65A	0.7949	1.1805	0.0523	0.037*
C66	0.63360 (19)	1.0827 (2)	0.08196 (13)	0.0242 (5)
H66A	0.6773	1.0076	0.1055	0.029*
C7	0.23595 (16)	1.02939 (17)	0.19891 (12)	0.0144 (4)
H7A	0.2396	1.1116	0.1582	0.017*
N8	0.13562 (14)	0.96748 (14)	0.17550 (10)	0.0154 (4)
C8	0.02745 (17)	1.05122 (18)	0.13919 (12)	0.0166 (4)
H8A	−0.0084	1.0900	0.1792	0.020*
H8B	−0.0415	1.0053	0.1271	0.020*
C81	0.06944 (17)	1.14699 (18)	0.06151 (12)	0.0160 (4)
C82	0.11703 (17)	1.11623 (18)	−0.00669 (12)	0.0177 (4)
H82A	0.1227	1.0342	−0.0041	0.021*
C83	0.15619 (19)	1.2036 (2)	−0.07808 (13)	0.0238 (5)
H83A	0.1873	1.1814	−0.1242	0.029*
C84	0.14968 (19)	1.3235 (2)	−0.08184 (14)	0.0267 (5)
H84A	0.1773	1.3835	−0.1303	0.032*
C85	0.1030 (2)	1.3554 (2)	−0.01507 (15)	0.0282 (5)
H85A	0.0986	1.4375	−0.0178	0.034*
C86	0.06221 (18)	1.26773 (19)	0.05641 (14)	0.0226 (5)
H86A	0.0293	1.2906	0.1019	0.027*
C9	0.09238 (17)	0.86057 (17)	0.24014 (12)	0.0161 (4)
H9A	0.0071	0.8397	0.2256	0.019*
N10	0.18222 (14)	0.75827 (15)	0.24740 (10)	0.0169 (4)
C10	0.15922 (18)	0.69695 (18)	0.18854 (13)	0.0206 (5)
H10A	0.1579	0.7565	0.1332	0.025*
H10B	0.0735	0.6613	0.2011	0.025*
C101	0.25975 (19)	0.59888 (18)	0.18856 (12)	0.0191 (4)
C102	0.22674 (19)	0.49958 (19)	0.16819 (13)	0.0221 (5)
H10C	0.1396	0.4903	0.1587	0.026*
C103	0.3199 (2)	0.41333 (19)	0.16149 (13)	0.0257 (5)
H10D	0.2966	0.3464	0.1466	0.031*
C104	0.4466 (2)	0.4257 (2)	0.17671 (13)	0.0260 (5)
H10E	0.5107	0.3675	0.1719	0.031*
C105	0.4798 (2)	0.5233 (2)	0.19889 (13)	0.0252 (5)
H10F	0.5665	0.5310	0.2103	0.030*
C106	0.38711 (19)	0.60983 (19)	0.20453 (13)	0.0218 (5)
H10G	0.4107	0.6768	0.2194	0.026*
C11	0.16760 (19)	0.68257 (18)	0.33223 (12)	0.0197 (4)
H11A	0.2425	0.6260	0.3483	0.024*
H11B	0.0883	0.6365	0.3416	0.024*
N12	0.15998 (15)	0.76935 (15)	0.37690 (10)	0.0174 (4)
C12	0.10752 (19)	0.72256 (19)	0.46067 (12)	0.0216 (5)
H12A	0.0207	0.6930	0.4595	0.026*
H12B	0.0979	0.7892	0.4842	0.026*
C121	0.1887 (2)	0.62217 (19)	0.51597 (13)	0.0219 (5)
C122	0.1292 (2)	0.52605 (19)	0.57210 (13)	0.0262 (5)
H12C	0.0383	0.5215	0.5727	0.031*
C123	0.1998 (2)	0.4361 (2)	0.62754 (14)	0.0306 (5)
H12D	0.1573	0.3708	0.6658	0.037*
C124	0.3311 (2)	0.4418 (2)	0.62686 (15)	0.0346 (6)
H12E	0.3798	0.3812	0.6651	0.042*
C125	0.3920 (2)	0.5362 (2)	0.57026 (18)	0.0462 (7)
H12F	0.4829	0.5398	0.5696	0.055*
C126	0.3218 (2)	0.6258 (2)	0.51428 (16)	0.0381 (6)
H12G	0.3648	0.6895	0.4749	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0120 (9)	0.0193 (11)	0.0166 (11)	−0.0024 (8)	0.0007 (8)	−0.0030 (9)
N2	0.0141 (8)	0.0162 (9)	0.0167 (9)	0.0000 (7)	0.0015 (7)	−0.0046 (7)
C2	0.0175 (9)	0.0238 (11)	0.0143 (11)	−0.0022 (8)	0.0023 (8)	−0.0067 (9)
C21	0.0164 (9)	0.0216 (11)	0.0179 (11)	0.0003 (8)	0.0036 (8)	−0.0097 (9)
C22	0.0202 (10)	0.0272 (12)	0.0343 (13)	−0.0029 (9)	0.0031 (9)	−0.0159 (11)
C23	0.0319 (12)	0.0147 (11)	0.0468 (16)	0.0001 (9)	0.0079 (11)	−0.0078 (11)
C24	0.0225 (11)	0.0256 (13)	0.0386 (15)	0.0080 (10)	0.0009 (10)	−0.0025 (11)
C25	0.0174 (10)	0.0305 (13)	0.0283 (13)	0.0028 (9)	−0.0007 (9)	−0.0079 (11)
C26	0.0190 (10)	0.0180 (11)	0.0203 (11)	−0.0023 (8)	0.0044 (8)	−0.0057 (9)
C3	0.0145 (9)	0.0136 (10)	0.0155 (10)	0.0001 (8)	−0.0012 (8)	−0.0023 (8)
N4	0.0134 (8)	0.0203 (9)	0.0148 (9)	−0.0005 (7)	−0.0016 (7)	−0.0058 (7)
C4	0.0165 (9)	0.0267 (12)	0.0124 (10)	−0.0006 (8)	−0.0022 (8)	−0.0042 (9)
C41	0.0136 (9)	0.0280 (12)	0.0174 (11)	−0.0041 (8)	−0.0028 (8)	−0.0081 (9)
C42	0.0150 (9)	0.0278 (12)	0.0158 (11)	−0.0017 (8)	−0.0030 (8)	−0.0046 (9)
C43	0.0198 (10)	0.0381 (14)	0.0187 (12)	−0.0027 (9)	−0.0013 (9)	−0.0139 (10)
C44	0.0343 (12)	0.0319 (13)	0.0291 (13)	−0.0102 (10)	0.0015 (10)	−0.0180 (11)
C45	0.0445 (14)	0.0265 (13)	0.0261 (13)	−0.0139 (11)	0.0035 (11)	−0.0095 (11)
C46	0.0316 (12)	0.0319 (13)	0.0196 (12)	−0.0123 (10)	0.0053 (9)	−0.0122 (10)
C5	0.0183 (9)	0.0099 (10)	0.0138 (10)	−0.0034 (8)	0.0013 (8)	−0.0011 (8)
C51	0.0169 (9)	0.0216 (11)	0.0155 (11)	−0.0010 (8)	−0.0004 (8)	−0.0066 (9)
N5	0.0162 (8)	0.0167 (9)	0.0152 (9)	−0.0011 (7)	0.0001 (7)	0.0000 (7)
O5A	0.0112 (6)	0.0253 (8)	0.0243 (8)	0.0014 (6)	−0.0030 (6)	−0.0051 (7)
O5B	0.0207 (7)	0.0189 (8)	0.0234 (8)	−0.0016 (6)	−0.0047 (6)	−0.0087 (7)
N6	0.0113 (7)	0.0181 (9)	0.0128 (9)	−0.0013 (6)	−0.0006 (6)	−0.0046 (7)
C6	0.0168 (9)	0.0225 (11)	0.0113 (10)	0.0013 (8)	−0.0017 (8)	−0.0055 (9)
C61	0.0184 (9)	0.0246 (11)	0.0084 (10)	−0.0007 (8)	0.0007 (8)	−0.0055 (9)
C62	0.0201 (10)	0.0289 (13)	0.0161 (11)	0.0011 (9)	0.0013 (8)	−0.0017 (10)
C63	0.0360 (12)	0.0231 (12)	0.0205 (12)	0.0019 (10)	0.0055 (10)	0.0017 (10)
C64	0.0382 (13)	0.0322 (14)	0.0211 (12)	−0.0163 (11)	0.0065 (10)	−0.0040 (11)
C65	0.0189 (10)	0.0457 (15)	0.0231 (12)	−0.0097 (10)	−0.0017 (9)	−0.0016 (11)
C66	0.0195 (10)	0.0303 (13)	0.0163 (11)	0.0012 (9)	0.0002 (8)	0.0014 (10)
C7	0.0132 (9)	0.0142 (10)	0.0132 (10)	−0.0004 (8)	−0.0019 (7)	−0.0005 (8)
N8	0.0123 (7)	0.0170 (9)	0.0153 (9)	−0.0004 (6)	−0.0036 (6)	−0.0025 (7)
C8	0.0134 (9)	0.0208 (11)	0.0148 (10)	−0.0001 (8)	−0.0022 (8)	−0.0040 (9)
C81	0.0096 (8)	0.0204 (11)	0.0174 (10)	0.0006 (8)	−0.0046 (8)	−0.0047 (9)
C82	0.0152 (9)	0.0198 (11)	0.0175 (11)	−0.0012 (8)	−0.0041 (8)	−0.0043 (9)
C83	0.0193 (10)	0.0317 (13)	0.0171 (11)	−0.0014 (9)	−0.0028 (8)	−0.0027 (10)
C84	0.0209 (10)	0.0261 (13)	0.0232 (12)	−0.0025 (9)	−0.0049 (9)	0.0071 (10)
C85	0.0261 (11)	0.0160 (11)	0.0384 (14)	0.0018 (9)	−0.0063 (10)	−0.0023 (11)
C86	0.0201 (10)	0.0229 (12)	0.0249 (12)	0.0036 (9)	−0.0038 (9)	−0.0079 (10)
C9	0.0140 (9)	0.0165 (10)	0.0170 (11)	−0.0026 (8)	−0.0006 (8)	−0.0039 (9)
N10	0.0180 (8)	0.0161 (9)	0.0159 (9)	0.0005 (7)	−0.0025 (7)	−0.0040 (7)
C10	0.0206 (10)	0.0193 (11)	0.0217 (12)	−0.0003 (9)	−0.0055 (9)	−0.0053 (9)
C101	0.0233 (10)	0.0174 (11)	0.0146 (10)	−0.0008 (8)	0.0011 (8)	−0.0023 (9)
C102	0.0221 (10)	0.0233 (12)	0.0197 (11)	−0.0039 (9)	−0.0010 (9)	−0.0047 (9)
C103	0.0384 (12)	0.0162 (11)	0.0227 (12)	−0.0009 (9)	−0.0010 (10)	−0.0064 (10)
C104	0.0290 (11)	0.0242 (12)	0.0229 (12)	0.0069 (9)	0.0008 (9)	−0.0065 (10)
C105	0.0205 (10)	0.0300 (13)	0.0242 (12)	0.0005 (9)	−0.0018 (9)	−0.0075 (10)
C106	0.0245 (10)	0.0225 (12)	0.0187 (11)	−0.0033 (9)	0.0010 (9)	−0.0070 (9)
C11	0.0207 (10)	0.0174 (11)	0.0190 (11)	−0.0017 (8)	−0.0007 (8)	−0.0028 (9)
N12	0.0192 (8)	0.0157 (9)	0.0145 (9)	0.0006 (7)	−0.0007 (7)	−0.0009 (7)
C12	0.0253 (10)	0.0217 (11)	0.0143 (11)	0.0004 (9)	0.0006 (9)	−0.0011 (9)
C121	0.0320 (11)	0.0182 (11)	0.0149 (11)	−0.0012 (9)	−0.0043 (9)	−0.0036 (9)
C122	0.0335 (12)	0.0231 (12)	0.0204 (12)	−0.0001 (10)	0.0029 (10)	−0.0053 (10)
C123	0.0491 (14)	0.0204 (12)	0.0185 (12)	0.0002 (11)	0.0008 (11)	−0.0013 (10)
C124	0.0553 (16)	0.0182 (12)	0.0292 (14)	0.0032 (11)	−0.0240 (12)	−0.0028 (11)
C125	0.0393 (14)	0.0294 (14)	0.0629 (19)	−0.0077 (11)	−0.0304 (14)	0.0009 (14)
C126	0.0355 (13)	0.0225 (13)	0.0465 (16)	−0.0090 (10)	−0.0139 (12)	0.0063 (12)

Geometric parameters (Å, º)

C1—N2	1.435 (2)	C62—C63	1.382 (3)
C1—N12	1.479 (2)	C63—C64	1.381 (3)
C1—C9	1.552 (3)	C64—C65	1.378 (3)
N2—C3	1.424 (2)	C65—C66	1.389 (3)
N2—C2	1.468 (2)	C7—N8	1.450 (2)
C2—C21	1.510 (3)	N8—C9	1.464 (2)
C21—C22	1.387 (3)	N8—C8	1.484 (2)
C21—C26	1.398 (3)	C8—C81	1.513 (3)
C22—C23	1.391 (3)	C81—C86	1.392 (3)
C23—C24	1.379 (3)	C81—C82	1.398 (3)
C24—C25	1.381 (3)	C82—C83	1.388 (3)
C25—C26	1.384 (3)	C83—C84	1.389 (3)
C3—N4	1.489 (2)	C84—C85	1.379 (3)
C3—C7	1.547 (3)	C85—C86	1.396 (3)
N4—C5	1.353 (2)	C9—N10	1.462 (2)
N4—C4	1.457 (2)	N10—C10	1.458 (3)
C4—C41	1.510 (3)	N10—C11	1.458 (3)
C41—C46	1.396 (3)	C10—C101	1.516 (3)
C41—C42	1.397 (3)	C101—C102	1.387 (3)
C42—C43	1.388 (3)	C101—C106	1.391 (3)
C43—C44	1.387 (3)	C102—C103	1.394 (3)
C44—C45	1.388 (3)	C103—C104	1.385 (3)
C45—C46	1.388 (3)	C104—C105	1.386 (3)
C5—N6	1.344 (2)	C105—C106	1.388 (3)
C5—C51	1.420 (3)	C11—N12	1.459 (3)
C51—N5	1.359 (2)	N12—C12	1.461 (3)
N5—O5B	1.258 (2)	C12—C121	1.513 (3)
N5—O5A	1.2738 (19)	C121—C122	1.383 (3)
N6—C7	1.475 (2)	C121—C126	1.388 (3)
N6—C6	1.478 (2)	C122—C123	1.389 (3)
C6—C61	1.511 (3)	C123—C124	1.373 (3)
C61—C66	1.395 (3)	C124—C125	1.381 (4)
C61—C62	1.397 (3)	C125—C126	1.390 (3)
N2—C1—N12	113.51 (15)	C65—C64—C63	119.6 (2)
N2—C1—C9	113.72 (16)	C64—C65—C66	120.4 (2)
N12—C1—C9	104.29 (15)	C65—C66—C61	120.9 (2)
C3—N2—C1	119.55 (15)	N8—C7—N6	112.99 (15)
C3—N2—C2	119.09 (16)	N8—C7—C3	116.25 (15)
C1—N2—C2	121.22 (15)	N6—C7—C3	104.84 (14)
N2—C2—C21	113.62 (16)	C7—N8—C9	114.19 (15)
C22—C21—C26	118.54 (19)	C7—N8—C8	111.40 (15)
C22—C21—C2	121.59 (18)	C9—N8—C8	112.55 (14)
C26—C21—C2	119.84 (18)	N8—C8—C81	111.91 (14)
C21—C22—C23	120.6 (2)	C86—C81—C82	118.48 (19)
C24—C23—C22	120.0 (2)	C86—C81—C8	120.79 (18)
C23—C24—C25	120.1 (2)	C82—C81—C8	120.73 (18)
C24—C25—C26	119.9 (2)	C83—C82—C81	121.06 (19)
C25—C26—C21	120.8 (2)	C82—C83—C84	119.7 (2)
N2—C3—N4	115.51 (15)	C85—C84—C83	119.9 (2)
N2—C3—C7	114.32 (16)	C84—C85—C86	120.4 (2)
N4—C3—C7	101.23 (14)	C81—C86—C85	120.4 (2)
C5—N4—C4	126.72 (16)	N10—C9—N8	111.21 (15)
C5—N4—C3	112.26 (15)	N10—C9—C1	104.46 (15)
C4—N4—C3	119.57 (15)	N8—C9—C1	116.32 (16)
N4—C4—C41	111.77 (17)	C10—N10—C11	113.75 (16)
C46—C41—C42	118.3 (2)	C10—N10—C9	112.08 (15)
C46—C41—C4	121.49 (18)	C11—N10—C9	105.13 (15)
C42—C41—C4	120.10 (19)	N10—C10—C101	113.14 (16)
C43—C42—C41	120.8 (2)	C102—C101—C106	119.06 (18)
C44—C43—C42	120.2 (2)	C102—C101—C10	119.98 (18)
C43—C44—C45	119.7 (2)	C106—C101—C10	120.87 (18)
C46—C45—C44	120.0 (2)	C101—C102—C103	120.78 (19)
C45—C46—C41	120.9 (2)	C104—C103—C102	119.7 (2)
N6—C5—N4	110.67 (16)	C103—C104—C105	119.84 (19)
N6—C5—C51	129.85 (18)	C104—C105—C106	120.4 (2)
N4—C5—C51	119.12 (17)	C105—C106—C101	120.3 (2)
N5—C51—C5	126.81 (18)	N10—C11—N12	102.93 (15)
O5B—N5—O5A	120.18 (15)	C11—N12—C12	114.32 (16)
O5B—N5—C51	121.79 (16)	C11—N12—C1	104.87 (15)
O5A—N5—C51	118.02 (16)	C12—N12—C1	111.11 (15)
C5—N6—C7	110.57 (15)	N12—C12—C121	114.28 (16)
C5—N6—C6	127.34 (15)	C122—C121—C126	118.7 (2)
C7—N6—C6	116.54 (15)	C122—C121—C12	119.50 (19)
N6—C6—C61	112.49 (16)	C126—C121—C12	121.8 (2)
C66—C61—C62	117.7 (2)	C121—C122—C123	121.2 (2)
C66—C61—C6	121.05 (18)	C124—C123—C122	119.8 (2)
C62—C61—C6	121.27 (17)	C123—C124—C125	119.7 (2)
C63—C62—C61	121.20 (19)	C124—C125—C126	120.7 (2)
C64—C63—C62	120.3 (2)	C121—C126—C125	119.9 (2)
N12—C1—N2—C3	79.3 (2)	N2—C3—C7—N8	5.4 (2)
C9—C1—N2—C3	−39.7 (2)	N4—C3—C7—N8	130.25 (16)
N12—C1—N2—C2	−105.03 (19)	N2—C3—C7—N6	−120.15 (16)
C9—C1—N2—C2	135.94 (17)	N4—C3—C7—N6	4.70 (19)
C3—N2—C2—C21	71.8 (2)	N6—C7—N8—C9	78.38 (19)
C1—N2—C2—C21	−103.9 (2)	C3—C7—N8—C9	−42.9 (2)
N2—C2—C21—C22	−102.5 (2)	N6—C7—N8—C8	−152.75 (15)
N2—C2—C21—C26	75.4 (2)	C3—C7—N8—C8	85.94 (19)
C26—C21—C22—C23	−1.0 (3)	C7—N8—C8—C81	62.4 (2)
C2—C21—C22—C23	176.93 (19)	C9—N8—C8—C81	−167.87 (16)
C21—C22—C23—C24	0.4 (3)	N8—C8—C81—C86	−117.16 (19)
C22—C23—C24—C25	0.6 (3)	N8—C8—C81—C82	62.5 (2)
C23—C24—C25—C26	−1.0 (3)	C86—C81—C82—C83	−0.1 (3)
C24—C25—C26—C21	0.4 (3)	C8—C81—C82—C83	−179.76 (17)
C22—C21—C26—C25	0.6 (3)	C81—C82—C83—C84	0.8 (3)
C2—C21—C26—C25	−177.32 (18)	C82—C83—C84—C85	−0.8 (3)
C1—N2—C3—N4	−79.6 (2)	C83—C84—C85—C86	0.0 (3)
C2—N2—C3—N4	104.71 (19)	C82—C81—C86—C85	−0.7 (3)
C1—N2—C3—C7	37.3 (2)	C8—C81—C86—C85	179.00 (18)
C2—N2—C3—C7	−138.40 (17)	C84—C85—C86—C81	0.7 (3)
N2—C3—N4—C5	122.50 (18)	C7—N8—C9—N10	−79.14 (19)
C7—C3—N4—C5	−1.5 (2)	C8—N8—C9—N10	152.58 (16)
N2—C3—N4—C4	−44.7 (2)	C7—N8—C9—C1	40.3 (2)
C7—C3—N4—C4	−168.73 (17)	C8—N8—C9—C1	−88.03 (19)
C5—N4—C4—C41	131.66 (19)	N2—C1—C9—N10	122.62 (16)
C3—N4—C4—C41	−63.2 (2)	N12—C1—C9—N10	−1.54 (19)
N4—C4—C41—C46	−28.2 (3)	N2—C1—C9—N8	−0.4 (2)
N4—C4—C41—C42	148.89 (17)	N12—C1—C9—N8	−124.52 (16)
C46—C41—C42—C43	0.9 (3)	N8—C9—N10—C10	−83.20 (19)
C4—C41—C42—C43	−176.23 (17)	C1—C9—N10—C10	150.56 (16)
C41—C42—C43—C44	1.0 (3)	N8—C9—N10—C11	152.76 (16)
C42—C43—C44—C45	−1.2 (3)	C1—C9—N10—C11	26.51 (18)
C43—C44—C45—C46	−0.6 (3)	C11—N10—C10—C101	−67.1 (2)
C44—C45—C46—C41	2.6 (3)	C9—N10—C10—C101	173.83 (16)
C42—C41—C46—C45	−2.8 (3)	N10—C10—C101—C102	150.15 (19)
C4—C41—C46—C45	174.37 (19)	N10—C10—C101—C106	−33.3 (3)
C4—N4—C5—N6	163.41 (18)	C106—C101—C102—C103	−1.8 (3)
C3—N4—C5—N6	−2.7 (2)	C10—C101—C102—C103	174.82 (19)
C4—N4—C5—C51	−22.8 (3)	C101—C102—C103—C104	1.1 (3)
C3—N4—C5—C51	171.11 (17)	C102—C103—C104—C105	0.3 (3)
N6—C5—C51—N5	−29.1 (3)	C103—C104—C105—C106	−1.1 (3)
N4—C5—C51—N5	158.46 (19)	C104—C105—C106—C101	0.5 (3)
C5—C51—N5—O5B	−11.7 (3)	C102—C101—C106—C105	1.0 (3)
C5—C51—N5—O5A	169.41 (19)	C10—C101—C106—C105	−175.60 (19)
N4—C5—N6—C7	6.0 (2)	C10—N10—C11—N12	−165.09 (14)
C51—C5—N6—C7	−166.9 (2)	C9—N10—C11—N12	−42.11 (18)
N4—C5—N6—C6	158.47 (18)	N10—C11—N12—C12	162.75 (15)
C51—C5—N6—C6	−14.5 (3)	N10—C11—N12—C1	40.83 (18)
C5—N6—C6—C61	−62.6 (2)	N2—C1—N12—C11	−148.21 (16)
C7—N6—C6—C61	88.42 (19)	C9—C1—N12—C11	−23.91 (18)
N6—C6—C61—C66	100.7 (2)	N2—C1—N12—C12	87.80 (19)
N6—C6—C61—C62	−78.6 (2)	C9—C1—N12—C12	−147.91 (16)
C66—C61—C62—C63	−2.5 (3)	C11—N12—C12—C121	64.0 (2)
C6—C61—C62—C63	176.83 (19)	C1—N12—C12—C121	−177.57 (17)
C61—C62—C63—C64	1.3 (3)	N12—C12—C121—C122	−140.5 (2)
C62—C63—C64—C65	0.8 (3)	N12—C12—C121—C126	42.0 (3)
C63—C64—C65—C66	−1.5 (4)	C126—C121—C122—C123	1.8 (3)
C64—C65—C66—C61	0.2 (3)	C12—C121—C122—C123	−175.7 (2)
C62—C61—C66—C65	1.7 (3)	C121—C122—C123—C124	−0.2 (3)
C6—C61—C66—C65	−177.58 (19)	C122—C123—C124—C125	−0.9 (4)
C5—N6—C7—N8	−134.28 (17)	C123—C124—C125—C126	0.4 (4)
C6—N6—C7—N8	70.0 (2)	C122—C121—C126—C125	−2.3 (4)
C5—N6—C7—C3	−6.7 (2)	C12—C121—C126—C125	175.2 (2)
C6—N6—C7—C3	−162.45 (15)	C124—C125—C126—C121	1.2 (4)