Structures of alkyl-substituted Tröger's base derivatives illustrate the importance of Z′ for packing in the absence of strong crystal synthons

Vande Velde, C.M.L.; Tylleman, B.; Zeller, M.; Sergeyev, S.

doi:10.1107/S0108768110021981

Structures of alkyl-substituted Tröger's base derivatives illustrate the importance of Z′ for packing in the absence of strong crystal synthons

C. M. L. Vande Velde, B. Tylleman, M. Zeller and S. Sergeyev

Crystal structures of Tröger's base (5,11-methano-2,8-dimethyl-5,6,11,12-tetrahydrodibenzo[b,f][1,5]diazocine) analogues with the methyl groups replaced by ethyl, iso-propyl and tert-butyl groups were studied. The incidence of Z′ > 1 structures increases to rather conspicuous levels. The reasons behind this trend are expanded upon, and a possible explanation is given in the flexibility of the alkyl substituents and van der Waals stabilization. In combination these effects allow for an additional stabilization of the packing by small changes in the molecular conformations, thus expanding the size of the asymmetric unit.

Keywords: Tröger's base; crystal synthons; crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768110021981/ry5032sup1.cif Contains datablocks 2a, alpha3a, beta3a, gamma3a, 4a, 4b
	Text file https://doi.org/10.1107/S0108768110021981/ry5032sup2.txt CIF for substructures
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110021981/ry50322asup3.hkl Contains datablock 2a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110021981/ry5032alpha3asup4.hkl Contains datablock alpha3a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110021981/ry5032beta3asup5.hkl Contains datablock beta3a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110021981/ry5032gamma3asup6.hkl Contains datablock gamma3a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110021981/ry50324asup7.hkl Contains datablock 4a
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768110021981/ry50324bsup8.hkl Contains datablock 4b
	Portable Document Format (PDF) file https://doi.org/10.1107/S0108768110021981/ry5032sup9.pdf Tables of intermolecular contacts and sublimation enthalpies plus extra figures

CCDC references: 788859; 788860; 788861; 788862; 788863; 788864

Computing details top

Data collection: Bruker SAINT (Bruker, 2008) for (2a); Bruker APEXII for alpha3a, beta3a, gamma3a; Bruker Saint 7.43 for (4a); Bruker Saint for (4b). Cell refinement: Bruker SAINT (Bruker, 2008) for (2a); Bruker APEXII for alpha3a, beta3a, gamma3a; Bruker Saint 7.43 for (4a); Bruker Saint for (4b). Data reduction: Bruker SAINT (Bruker, 2008) for (2a); Bruker APEXII for alpha3a, beta3a, gamma3a; Bruker Saint 7.43 for (4a); Bruker Saint for (4b). Program(s) used to solve structure: SHELXS86 (Sheldrick, 2008) for (2a); SHELXS97 (Sheldrick, 2008) for alpha3a, beta3a, gamma3a, (4a), (4b). For all structures, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008). Molecular graphics: ORTEP-3 for Windows (Farrugia, 1997), Mercury (Bruno, 2002) for (2a); ORTEP, Mercury for alpha3a, beta3a, gamma3a, (4a), (4b). Software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2008) for (2a); WinGX, PLATON for alpha3a, beta3a, gamma3a, (4a), (4b).

2,8-diethyl-1,5-methanodibenzodiazocine (2a) top

Crystal data top

C₁₉H₂₂N₂	Z = 6
M_r = 278.40	F(000) = 900
Triclinic, P1	D_x = 1.193 Mg m⁻³
Hall symbol: -P1	Melting point = 325–326 K
a = 10.9907 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.8123 (14) Å	Cell parameters from 6620 reflections
c = 17.2240 (17) Å	θ = 0.9–31.3°
α = 71.469 (1)°	µ = 0.07 mm⁻¹
β = 88.621 (2)°	T = 100 K
γ = 70.319 (1)°	Block, colourless
V = 2324.2 (4) Å³	0.46 × 0.43 × 0.36 mm

Data collection top

Area detector diffractometer Bruker APEXII	13682 independent reflections
Radiation source: fine-focus sealed tube	10156 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω–scans	θ_max = 31.3°, θ_min = 1.3°
Absorption correction: multi-scan Bruker SADABS, 2008	h = −15→15
T_min = 0.899, T_max = 0.978	k = −19→19
27074 measured reflections	l = −24→25

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	Riding
S = 1.02	w = 1/[σ²(F_o²) + (0.0733P)² + 0.6033P] where P = (F_o² + 2F_c²)/3
13682 reflections	(Δ/σ)_max = 0.001
626 parameters	Δρ_max = 0.46 e Å⁻³
8 restraints	Δρ_min = −0.30 e Å⁻³

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.65063 (11)	0.88621 (9)	−0.04102 (7)	0.0205 (2)
H1	0.64582 (13)	0.9346 (7)	−0.0984 (8)	0.025*
C2	0.66991 (11)	0.92157 (9)	0.02351 (8)	0.0206 (2)
C3	0.67552 (12)	0.85210 (10)	0.10349 (8)	0.0239 (2)
H3	0.6872 (2)	0.8755 (4)	0.1503 (7)	0.029*
C4	0.66493 (12)	0.75046 (10)	0.11823 (8)	0.0234 (2)
H4	0.66991 (14)	0.7023 (7)	0.1755 (9)	0.028*
C4A	0.64733 (10)	0.71586 (9)	0.05299 (7)	0.0189 (2)
N5	0.64306 (10)	0.60806 (8)	0.07091 (7)	0.0226 (2)
C6	0.51748 (11)	0.60024 (10)	0.09778 (7)	0.0219 (2)
H6A	0.4906 (3)	0.6376 (4)	0.1392 (4)	0.026*
H6B	0.52795 (15)	0.5226 (8)	0.1246 (3)	0.026*
C6A	0.41205 (11)	0.65030 (9)	0.02725 (7)	0.0175 (2)
C7	0.28158 (11)	0.67220 (9)	0.04180 (7)	0.0203 (2)
H7	0.2586 (4)	0.6549 (3)	0.0992 (9)	0.024*
C8	0.18258 (11)	0.71770 (9)	−0.02203 (8)	0.0238 (2)
C9	0.21731 (13)	0.74116 (10)	−0.10253 (8)	0.0275 (3)
H9	0.1506 (11)	0.7726 (5)	−0.1479 (7)	0.033*
C10	0.34642 (13)	0.71985 (10)	−0.11830 (8)	0.0255 (3)
H10	0.3692 (4)	0.7374 (3)	−0.1763 (9)	0.031*
C10A	0.44492 (11)	0.67415 (9)	−0.05395 (7)	0.0192 (2)
N11	0.57744 (10)	0.65174 (8)	−0.07318 (7)	0.0240 (2)
C12	0.61269 (13)	0.75084 (11)	−0.09968 (8)	0.0249 (3)
H12A	0.5410 (8)	0.8115 (6)	−0.1385 (4)	0.030*
H12B	0.6922 (8)	0.73722 (17)	−0.1298 (3)	0.030*
C12A	0.63784 (11)	0.78501 (9)	−0.02770 (7)	0.0189 (2)
C13	0.66632 (12)	0.57373 (10)	−0.00163 (9)	0.0277 (3)
H13A	0.65608 (16)	0.5021 (8)	0.01070 (16)	0.033*
H13B	0.7567 (10)	0.56516 (14)	−0.01477 (16)	0.033*
C14	0.68428 (12)	1.03132 (10)	0.00644 (9)	0.0267 (3)
H14A	0.68474 (12)	1.0466 (2)	0.0591 (6)	0.032*
H14B	0.6079 (8)	1.0885 (6)	−0.0302 (4)	0.032*
C15	0.80712 (14)	1.03814 (11)	−0.03350 (10)	0.0343 (3)
H15A	0.8848 (8)	0.9808 (8)	0.0032 (5)	0.051*
H15B	0.8123 (5)	1.1120 (8)	−0.0422 (6)	0.051*
H15C	0.8056 (5)	1.0261 (9)	−0.0879 (6)	0.051*
C16	0.04256 (12)	0.73861 (11)	−0.00392 (10)	0.0341 (3)
H16A	−0.0141 (7)	0.7934 (7)	−0.0528 (6)	0.041*
H16B	0.0265 (2)	0.7690 (4)	0.0415 (5)	0.041*
C17	0.00691 (14)	0.63664 (13)	0.01929 (12)	0.0438 (4)
H17A	0.0199 (11)	0.6068 (6)	−0.0275 (6)	0.066*
H17B	−0.0863 (11)	0.6550 (3)	0.0314 (7)	0.066*
H17C	0.0636 (10)	0.5808 (7)	0.0693 (7)	0.066*
C21	0.32892 (12)	0.55399 (11)	0.30357 (9)	0.0267 (3)
H21	0.33306 (14)	0.5939 (7)	0.2471 (9)	0.032*
C22	0.34413 (14)	0.59660 (12)	0.36433 (10)	0.0346 (3)
C23	0.33607 (15)	0.53786 (14)	0.44501 (10)	0.0387 (4)
H23	0.3444 (2)	0.5662 (5)	0.4881 (8)	0.046*
C24	0.31640 (13)	0.43970 (13)	0.46480 (9)	0.0327 (3)
H24	0.31146 (16)	0.3998 (7)	0.5225 (10)	0.039*
C24A	0.30339 (11)	0.39649 (10)	0.40345 (8)	0.0230 (2)
N25	0.29185 (10)	0.29068 (9)	0.42683 (7)	0.0257 (2)
C26	0.16078 (12)	0.29170 (11)	0.44752 (8)	0.0264 (3)
H26A	0.1282 (4)	0.3382 (5)	0.4826 (4)	0.032*
H26B	0.16545 (13)	0.2166 (8)	0.4798 (4)	0.032*
C26A	0.06619 (11)	0.33399 (9)	0.37177 (7)	0.0187 (2)
C27	−0.06692 (11)	0.35998 (9)	0.37884 (7)	0.0205 (2)
H27	−0.0978 (5)	0.34887 (19)	0.4332 (8)	0.025*
C28	−0.15683 (11)	0.40132 (9)	0.31042 (8)	0.0221 (2)
C29	−0.11085 (12)	0.41820 (10)	0.23282 (8)	0.0248 (3)
H29	−0.1722 (10)	0.4487 (5)	0.1838 (8)	0.030*
C30	0.02090 (12)	0.39212 (10)	0.22457 (7)	0.0233 (2)
H30	0.0518 (5)	0.4044 (2)	0.1689 (9)	0.028*
C30A	0.11101 (11)	0.34868 (9)	0.29351 (7)	0.0191 (2)
N31	0.24716 (10)	0.31786 (8)	0.28263 (7)	0.0232 (2)
C32	0.29084 (13)	0.41233 (11)	0.25329 (8)	0.0249 (3)
H32A	0.2267 (7)	0.4710 (6)	0.2095 (5)	0.030*
H32B	0.3742 (9)	0.3910 (2)	0.2293 (3)	0.030*
C32A	0.30784 (11)	0.45511 (10)	0.32175 (8)	0.0212 (2)
C33	0.32411 (12)	0.24454 (10)	0.36017 (9)	0.0280 (3)
H33A	0.4193 (10)	0.2292 (2)	0.35232 (12)	0.034*
H33B	0.3082 (2)	0.1731 (8)	0.37594 (19)	0.034*
C34	0.3701 (2)	0.70243 (16)	0.34522 (14)	0.0566 (5)	0.648 (6)
H34A	0.3104 (8)	0.7480 (6)	0.3794 (5)	0.068*	0.648 (6)
H34B	0.4671 (14)	0.6835 (3)	0.3666 (4)	0.068*	0.648 (6)
C35	0.3493 (4)	0.7724 (2)	0.25859 (19)	0.0479 (10)	0.648 (6)
H35A	0.371 (2)	0.8364 (16)	0.2540 (3)	0.072*	0.648 (6)
H35B	0.259 (2)	0.7950 (15)	0.2386 (6)	0.072*	0.648 (6)
H35C	0.4041 (18)	0.7322 (10)	0.2259 (8)	0.072*	0.648 (6)
C34B	0.3701 (2)	0.70243 (16)	0.34522 (14)	0.0566 (5)	0.352 (6)
H34C	0.2825 (2)	0.7653 (13)	0.3212 (7)	0.068*	0.352 (6)
H34D	0.395 (2)	0.7080 (8)	0.4009 (10)	0.068*	0.352 (6)
C35B	0.4587 (8)	0.7229 (5)	0.2949 (5)	0.082 (3)	0.352 (6)
H35D	0.434 (3)	0.729 (5)	0.245 (3)	0.123*	0.352 (6)
H35E	0.534 (5)	0.669 (4)	0.312 (2)	0.123*	0.352 (6)
H35F	0.468 (4)	0.784 (5)	0.295 (3)	0.123*	0.352 (6)
C36	−0.30011 (12)	0.42663 (11)	0.32069 (9)	0.0301 (3)
H36A	−0.3504 (6)	0.4695 (5)	0.2660 (6)	0.036*
H36B	−0.3261 (3)	0.4724 (5)	0.3570 (4)	0.036*
C37	−0.33422 (14)	0.32473 (13)	0.35739 (13)	0.0483 (5)
H37A	−0.3116 (12)	0.2802 (7)	0.3205 (6)	0.072*
H37B	−0.4285 (11)	0.3455 (3)	0.3638 (7)	0.072*
H37C	−0.2848 (11)	0.2819 (7)	0.4119 (7)	0.072*
C41	0.37090 (12)	0.01851 (10)	0.29068 (8)	0.0229 (2)
H41	0.3855 (3)	0.0532 (5)	0.2336 (9)	0.027*
C42	0.47770 (12)	−0.04206 (10)	0.34852 (9)	0.0277 (3)
C43	0.45484 (15)	−0.08944 (11)	0.42882 (9)	0.0341 (3)
H43	0.5276 (13)	−0.1327 (8)	0.4703 (7)	0.041*
C44	0.32984 (15)	−0.07581 (11)	0.45047 (8)	0.0327 (3)
H44	0.3163 (3)	−0.1087 (6)	0.5060 (10)	0.039*
C44A	0.22278 (12)	−0.01442 (10)	0.39217 (7)	0.0225 (2)
N45	0.09483 (12)	−0.00028 (10)	0.41784 (7)	0.0311 (3)
C46	0.05939 (15)	−0.09806 (13)	0.43174 (8)	0.0335 (3)
H46A	−0.0164 (8)	−0.09294 (13)	0.4654 (4)	0.040*
H46B	0.1336 (8)	−0.1638 (8)	0.4636 (4)	0.040*
C46A	0.02525 (12)	−0.11123 (10)	0.35184 (7)	0.0223 (2)
C47	0.01358 (12)	−0.20852 (10)	0.35131 (8)	0.0252 (3)
H47	0.0274 (3)	−0.2684 (9)	0.4039 (8)	0.030*
C48	−0.01688 (12)	−0.22411 (10)	0.27935 (8)	0.0237 (2)
C49	−0.03470 (12)	−0.13853 (11)	0.20585 (8)	0.0255 (3)
H49	−0.0551 (3)	−0.14759 (18)	0.1539 (8)	0.031*
C50	−0.02416 (12)	−0.04089 (11)	0.20473 (8)	0.0252 (3)
H50	−0.0372 (2)	0.0180 (9)	0.1525 (8)	0.030*
C50A	0.00480 (11)	−0.02597 (9)	0.27744 (8)	0.0214 (2)
N51	0.00917 (10)	0.07806 (8)	0.27458 (7)	0.0272 (2)
C52	0.13038 (12)	0.09403 (10)	0.24507 (8)	0.0251 (3)
H52A	0.11769 (18)	0.1725 (8)	0.2275 (2)	0.030*
H52B	0.1507 (2)	0.0696 (3)	0.1966 (5)	0.030*
C52A	0.24385 (11)	0.03186 (9)	0.31068 (7)	0.0186 (2)
C53	−0.00183 (13)	0.08999 (12)	0.35593 (10)	0.0364 (3)
H53A	−0.0900 (10)	0.09380 (13)	0.3726 (2)	0.044*
H53B	0.00927 (18)	0.1594 (8)	0.35331 (11)	0.044*
C54	0.61345 (14)	−0.05292 (15)	0.32426 (12)	0.0456 (4)
H54A	0.61857 (16)	−0.05706 (16)	0.2684 (7)	0.055*
H54B	0.6747 (8)	−0.1212 (9)	0.3614 (5)	0.055*
C55	0.65377 (15)	0.04062 (17)	0.32685 (12)	0.0501 (5)
H55A	0.5895 (10)	0.1115 (8)	0.2902 (8)	0.075*
H55B	0.7428 (11)	0.0311 (6)	0.3069 (8)	0.075*
H55C	0.6559 (12)	0.0417 (7)	0.3851 (7)	0.075*
C56	−0.03500 (14)	−0.32869 (11)	0.28164 (10)	0.0323 (3)
H56A	0.0422 (9)	−0.3907 (7)	0.3109 (3)	0.039*
H56B	−0.04359 (16)	−0.32924 (11)	0.2252 (6)	0.039*
C57	−0.15437 (16)	−0.34172 (12)	0.32400 (9)	0.0351 (3)
H57A	−0.1432 (5)	−0.3468 (9)	0.3817 (6)	0.053*
H57B	−0.1656 (6)	−0.4083 (8)	0.3215 (6)	0.053*
H57C	−0.2313 (8)	−0.2785 (7)	0.2961 (5)	0.053*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0213 (6)	0.0213 (5)	0.0240 (6)	−0.0118 (4)	0.0060 (4)	−0.0095 (4)
C2	0.0156 (5)	0.0212 (5)	0.0312 (6)	−0.0086 (4)	0.0052 (4)	−0.0146 (5)
C3	0.0223 (6)	0.0315 (6)	0.0257 (6)	−0.0135 (5)	0.0026 (5)	−0.0154 (5)
C4	0.0214 (6)	0.0277 (6)	0.0230 (6)	−0.0119 (5)	−0.0019 (4)	−0.0072 (5)
C4A	0.0133 (5)	0.0178 (5)	0.0269 (6)	−0.0064 (4)	0.0003 (4)	−0.0080 (4)
N5	0.0175 (5)	0.0167 (4)	0.0325 (6)	−0.0064 (4)	−0.0029 (4)	−0.0059 (4)
C6	0.0212 (6)	0.0215 (5)	0.0227 (6)	−0.0113 (5)	−0.0030 (4)	−0.0022 (4)
C6A	0.0185 (5)	0.0143 (5)	0.0209 (5)	−0.0071 (4)	−0.0010 (4)	−0.0056 (4)
C7	0.0192 (5)	0.0184 (5)	0.0255 (6)	−0.0081 (4)	0.0026 (4)	−0.0086 (4)
C8	0.0175 (5)	0.0147 (5)	0.0389 (7)	−0.0041 (4)	−0.0024 (5)	−0.0098 (5)
C9	0.0285 (6)	0.0192 (6)	0.0308 (7)	−0.0071 (5)	−0.0121 (5)	−0.0030 (5)
C10	0.0340 (7)	0.0238 (6)	0.0216 (6)	−0.0142 (5)	−0.0021 (5)	−0.0063 (5)
C10A	0.0210 (5)	0.0175 (5)	0.0230 (5)	−0.0095 (4)	0.0022 (4)	−0.0089 (4)
N11	0.0259 (5)	0.0256 (5)	0.0311 (5)	−0.0150 (4)	0.0098 (4)	−0.0172 (4)
C12	0.0325 (7)	0.0301 (6)	0.0253 (6)	−0.0210 (5)	0.0119 (5)	−0.0164 (5)
C12A	0.0166 (5)	0.0211 (5)	0.0247 (6)	−0.0094 (4)	0.0058 (4)	−0.0123 (4)
C13	0.0195 (6)	0.0209 (6)	0.0475 (8)	−0.0069 (5)	0.0048 (5)	−0.0179 (5)
C14	0.0243 (6)	0.0229 (6)	0.0411 (7)	−0.0113 (5)	0.0066 (5)	−0.0184 (5)
C15	0.0311 (7)	0.0258 (6)	0.0556 (9)	−0.0169 (6)	0.0138 (6)	−0.0191 (6)
C16	0.0169 (6)	0.0279 (7)	0.0577 (9)	−0.0029 (5)	−0.0009 (6)	−0.0192 (6)
C17	0.0201 (7)	0.0388 (8)	0.0733 (12)	−0.0124 (6)	0.0076 (7)	−0.0174 (8)
C21	0.0268 (6)	0.0291 (6)	0.0327 (7)	−0.0158 (5)	0.0082 (5)	−0.0151 (5)
C22	0.0316 (7)	0.0384 (8)	0.0502 (9)	−0.0203 (6)	0.0106 (6)	−0.0281 (7)
C23	0.0354 (8)	0.0596 (10)	0.0432 (8)	−0.0260 (7)	0.0093 (6)	−0.0362 (8)
C24	0.0269 (7)	0.0530 (9)	0.0280 (7)	−0.0209 (6)	0.0037 (5)	−0.0191 (6)
C24A	0.0145 (5)	0.0298 (6)	0.0269 (6)	−0.0083 (5)	0.0000 (4)	−0.0113 (5)
N25	0.0192 (5)	0.0279 (5)	0.0283 (5)	−0.0101 (4)	−0.0032 (4)	−0.0045 (4)
C26	0.0221 (6)	0.0337 (7)	0.0211 (6)	−0.0145 (5)	−0.0028 (4)	−0.0008 (5)
C26A	0.0181 (5)	0.0174 (5)	0.0199 (5)	−0.0072 (4)	−0.0017 (4)	−0.0040 (4)
C27	0.0205 (6)	0.0196 (5)	0.0215 (5)	−0.0087 (4)	0.0004 (4)	−0.0052 (4)
C28	0.0189 (5)	0.0160 (5)	0.0294 (6)	−0.0057 (4)	−0.0032 (4)	−0.0049 (4)
C29	0.0272 (6)	0.0206 (5)	0.0239 (6)	−0.0082 (5)	−0.0083 (5)	−0.0031 (5)
C30	0.0310 (6)	0.0226 (6)	0.0189 (5)	−0.0124 (5)	−0.0010 (5)	−0.0069 (4)
C30A	0.0197 (5)	0.0173 (5)	0.0231 (5)	−0.0082 (4)	0.0016 (4)	−0.0081 (4)
N31	0.0213 (5)	0.0232 (5)	0.0304 (5)	−0.0102 (4)	0.0055 (4)	−0.0134 (4)
C32	0.0276 (6)	0.0298 (6)	0.0272 (6)	−0.0166 (5)	0.0103 (5)	−0.0159 (5)
C32A	0.0161 (5)	0.0247 (6)	0.0280 (6)	−0.0093 (4)	0.0056 (4)	−0.0136 (5)
C33	0.0196 (6)	0.0220 (6)	0.0411 (8)	−0.0053 (5)	0.0002 (5)	−0.0105 (5)
C34	0.0660 (12)	0.0515 (11)	0.0815 (14)	−0.0383 (10)	0.0162 (10)	−0.0421 (10)
C35	0.060 (2)	0.0352 (14)	0.0706 (19)	−0.0310 (14)	0.0297 (15)	−0.0330 (13)
C34B	0.0660 (12)	0.0515 (11)	0.0815 (14)	−0.0383 (10)	0.0162 (10)	−0.0421 (10)
C35B	0.089 (6)	0.057 (4)	0.152 (8)	−0.056 (4)	0.081 (6)	−0.075 (5)
C36	0.0182 (6)	0.0256 (6)	0.0404 (8)	−0.0045 (5)	−0.0039 (5)	−0.0056 (5)
C37	0.0208 (7)	0.0366 (8)	0.0810 (13)	−0.0135 (6)	−0.0032 (7)	−0.0064 (8)
C41	0.0231 (6)	0.0270 (6)	0.0224 (6)	−0.0112 (5)	0.0026 (4)	−0.0108 (5)
C42	0.0215 (6)	0.0248 (6)	0.0406 (7)	−0.0045 (5)	−0.0026 (5)	−0.0193 (6)
C43	0.0380 (8)	0.0229 (6)	0.0372 (8)	−0.0099 (6)	−0.0178 (6)	−0.0035 (5)
C44	0.0505 (9)	0.0346 (7)	0.0187 (6)	−0.0277 (7)	−0.0061 (5)	−0.0020 (5)
C44A	0.0295 (6)	0.0247 (6)	0.0223 (6)	−0.0169 (5)	0.0046 (5)	−0.0121 (5)
N45	0.0385 (6)	0.0433 (7)	0.0340 (6)	−0.0299 (6)	0.0177 (5)	−0.0266 (5)
C46	0.0474 (8)	0.0488 (8)	0.0275 (6)	−0.0369 (7)	0.0166 (6)	−0.0224 (6)
C46A	0.0240 (6)	0.0268 (6)	0.0252 (6)	−0.0145 (5)	0.0071 (4)	−0.0149 (5)
C47	0.0292 (6)	0.0256 (6)	0.0269 (6)	−0.0154 (5)	0.0046 (5)	−0.0104 (5)
C48	0.0200 (6)	0.0235 (6)	0.0340 (7)	−0.0091 (5)	0.0054 (5)	−0.0164 (5)
C49	0.0224 (6)	0.0330 (7)	0.0285 (6)	−0.0125 (5)	0.0025 (5)	−0.0169 (5)
C50	0.0201 (6)	0.0270 (6)	0.0277 (6)	−0.0091 (5)	−0.0023 (5)	−0.0065 (5)
C50A	0.0152 (5)	0.0197 (5)	0.0331 (6)	−0.0070 (4)	0.0024 (4)	−0.0127 (5)
N51	0.0188 (5)	0.0186 (5)	0.0458 (7)	−0.0058 (4)	−0.0019 (4)	−0.0132 (5)
C52	0.0229 (6)	0.0196 (5)	0.0294 (6)	−0.0089 (5)	−0.0065 (5)	−0.0011 (5)
C52A	0.0208 (5)	0.0150 (5)	0.0207 (5)	−0.0070 (4)	−0.0005 (4)	−0.0057 (4)
C53	0.0249 (7)	0.0376 (8)	0.0657 (10)	−0.0157 (6)	0.0163 (6)	−0.0379 (8)
C54	0.0203 (7)	0.0581 (10)	0.0711 (11)	−0.0054 (7)	0.0041 (7)	−0.0467 (9)
C55	0.0247 (7)	0.0759 (13)	0.0704 (12)	−0.0237 (8)	0.0171 (7)	−0.0455 (10)
C56	0.0314 (7)	0.0244 (6)	0.0486 (8)	−0.0101 (5)	0.0011 (6)	−0.0213 (6)
C57	0.0515 (9)	0.0319 (7)	0.0348 (7)	−0.0279 (7)	0.0037 (6)	−0.0137 (6)

Geometric parameters (Å, º) top

C1—C2	1.3945 (16)	C30—H30	0.9910
C1—C12A	1.3975 (15)	C30A—N31	1.4364 (15)
C1—H1	0.9930	N31—C33	1.4637 (17)
C2—C3	1.3951 (17)	N31—C32	1.4764 (15)
C2—C14	1.5117 (16)	C32—C32A	1.5173 (16)
C3—C4	1.3896 (17)	C32—H32A	0.9872
C3—H3	0.9851	C32—H32B	0.9872
C4—C4A	1.3938 (16)	C33—H33A	1.0102
C4—H4	0.9893	C33—H33B	1.0102
C4A—C12A	1.3968 (16)	C34—C35	1.471 (4)
C4A—N5	1.4383 (14)	C34—H34A	1.0546
N5—C13	1.4597 (17)	C34—H34B	1.0546
N5—C6	1.4727 (15)	C34B—C35B	1.331 (6)
C6—C6A	1.5136 (16)	C35—H35A	0.9726
C6—H6A	0.9909	C35—H35B	0.9726
C6—H6B	0.9909	C35—H35C	0.9726
C6A—C7	1.3961 (16)	C35B—H35D	0.8830
C6A—C10A	1.3993 (16)	C35B—H35E	0.8830
C7—C8	1.3948 (17)	C35B—H35F	0.8830
C7—H7	0.9889	C36—C37	1.516 (2)
C8—C9	1.3949 (19)	C36—H36A	0.9962
C8—C16	1.5112 (17)	C36—H36B	0.9962
C9—C10	1.3873 (19)	C37—H37A	0.9912
C9—H9	0.9660	C37—H37B	0.9912
C10—C10A	1.3971 (17)	C37—H37C	0.9912
C10—H10	0.9977	C41—C42	1.3912 (17)
C10A—N11	1.4371 (15)	C41—C52A	1.3952 (16)
N11—C13	1.4625 (17)	C41—H41	0.9826
N11—C12	1.4776 (15)	C42—C43	1.387 (2)
C12—C12A	1.5208 (15)	C42—C54	1.5108 (19)
C12—H12A	0.9980	C43—C44	1.381 (2)
C12—H12B	0.9980	C43—H43	0.9702
C13—H13A	0.9890	C44—C44A	1.3984 (19)
C13—H13B	0.9890	C44—H44	0.9516
C14—C15	1.5181 (18)	C44A—C52A	1.3951 (16)
C14—H14A	0.9948	C44A—N45	1.4321 (16)
C14—H14B	0.9948	N45—C53	1.462 (2)
C15—H15A	1.0043	N45—C46	1.4756 (16)
C15—H15B	1.0044	C46—C46A	1.5158 (17)
C15—H15C	1.0044	C46—H46A	0.9987
C16—C17	1.518 (2)	C46—H46B	0.9987
C16—H16A	0.9864	C46A—C47	1.3952 (16)
C16—H16B	0.9864	C46A—C50A	1.3985 (17)
C17—H17A	1.0024	C47—C48	1.3902 (17)
C17—H17B	1.0024	C47—H47	0.9865
C17—H17C	1.0024	C48—C49	1.3940 (18)
C21—C22	1.3914 (18)	C48—C56	1.5115 (17)
C21—C32A	1.3982 (16)	C49—C50	1.3862 (17)
C21—H21	0.9625	C49—H49	0.9835
C22—C23	1.387 (2)	C50—C50A	1.3926 (17)
C22—C34	1.515 (2)	C50—H50	0.9770
C23—C24	1.379 (2)	C50A—N51	1.4390 (15)
C23—H23	0.9605	N51—C53	1.4597 (19)
C24—C24A	1.3997 (17)	N51—C52	1.4751 (16)
C24—H24	0.9811	C52—C52A	1.5163 (16)
C24A—C32A	1.3917 (17)	C52—H52A	0.9892
C24A—N25	1.4362 (16)	C52—H52B	0.9892
N25—C33	1.4641 (17)	C53—H53A	0.9928
N25—C26	1.4722 (16)	C53—H53B	0.9928
C26—C26A	1.5153 (16)	C54—C55	1.514 (2)
C26—H26A	0.9928	C54—H54A	0.9805
C26—H26B	0.9928	C54—H54B	0.9805
C26A—C27	1.3963 (16)	C55—H55A	1.0094
C26A—C30A	1.4008 (16)	C55—H55B	1.0094
C27—C28	1.3926 (16)	C55—H55C	1.0094
C27—H27	0.9722	C56—C57	1.522 (2)
C28—C29	1.3947 (18)	C56—H56A	0.9820
C28—C36	1.5128 (17)	C56—H56B	0.9820
C29—C30	1.3850 (18)	C57—H57A	0.9819
C29—H29	0.9773	C57—H57B	0.9819
C30—C30A	1.3980 (16)	C57—H57C	0.9819

C2—C1—C12A	122.30 (11)	C26A—C30A—N31	121.60 (10)
C2—C1—H1	118.9	C30A—N31—C33	110.57 (10)
C12A—C1—H1	118.9	C30A—N31—C32	112.65 (9)
C1—C2—C3	117.58 (10)	C33—N31—C32	107.80 (10)
C1—C2—C14	120.63 (11)	N31—C32—C32A	112.24 (10)
C3—C2—C14	121.79 (11)	N31—C32—H32A	109.2
C4—C3—C2	121.15 (11)	C32A—C32—H32A	109.2
C4—C3—H3	119.4	N31—C32—H32B	109.2
C2—C3—H3	119.4	C32A—C32—H32B	109.2
C3—C4—C4A	120.50 (11)	H32A—C32—H32B	107.9
C3—C4—H4	119.7	C24A—C32A—C21	119.02 (11)
C4A—C4—H4	119.7	C24A—C32A—C32	120.66 (11)
C4—C4A—C12A	119.52 (10)	C21—C32A—C32	120.32 (11)
C4—C4A—N5	118.72 (11)	N31—C33—N25	112.03 (10)
C12A—C4A—N5	121.74 (10)	N31—C33—H33A	109.2
C4A—N5—C13	110.51 (10)	N25—C33—H33A	109.2
C4A—N5—C6	112.84 (9)	N31—C33—H33B	109.2
C13—N5—C6	107.64 (9)	N25—C33—H33B	109.2
N5—C6—C6A	112.52 (10)	H33A—C33—H33B	107.9
N5—C6—H6A	109.1	C35—C34—C22	117.14 (16)
C6A—C6—H6A	109.1	C35B—C34B—C22	121.0 (3)
N5—C6—H6B	109.1	C22—C34—H34A	108.0
C6A—C6—H6B	109.1	C22—C34—H34B	108.0
H6A—C6—H6B	107.8	C22—C34B—H34C	107.1
C7—C6A—C10A	119.07 (10)	C22—C34B—H34D	107.1
C7—C6A—C6	120.97 (10)	H35D—C35B—H35E	109.5
C10A—C6A—C6	119.96 (10)	H35D—C35B—H35F	109.5
C8—C7—C6A	122.15 (11)	H35E—C35B—H35F	109.5
C8—C7—H7	118.9	C28—C36—C37	112.50 (11)
C6A—C7—H7	118.9	C28—C36—H36A	109.1
C7—C8—C9	117.91 (11)	C37—C36—H36A	109.1
C7—C8—C16	120.67 (12)	C28—C36—H36B	109.1
C9—C8—C16	121.40 (12)	C37—C36—H36B	109.1
C10—C9—C8	120.83 (11)	H36A—C36—H36B	107.8
C10—C9—H9	119.6	C36—C37—H37A	109.5
C8—C9—H9	119.6	C36—C37—H37B	109.5
C9—C10—C10A	120.84 (12)	H37A—C37—H37B	109.5
C9—C10—H10	119.6	C36—C37—H37C	109.5
C10A—C10—H10	119.6	H37A—C37—H37C	109.5
C10—C10A—C6A	119.20 (11)	H37B—C37—H37C	109.5
C10—C10A—N11	118.90 (11)	C42—C41—C52A	122.43 (12)
C6A—C10A—N11	121.90 (10)	C42—C41—H41	118.8
C10A—N11—C13	110.77 (10)	C52A—C41—H41	118.8
C10A—N11—C12	112.26 (9)	C43—C42—C41	117.83 (12)
C13—N11—C12	107.67 (10)	C43—C42—C54	121.60 (13)
N11—C12—C12A	112.38 (10)	C41—C42—C54	120.55 (13)
N11—C12—H12A	109.1	C44—C43—C42	120.84 (12)
C12A—C12—H12A	109.1	C44—C43—H43	119.6
N11—C12—H12B	109.1	C42—C43—H43	119.6
C12A—C12—H12B	109.1	C43—C44—C44A	121.11 (12)
H12A—C12—H12B	107.9	C43—C44—H44	119.4
C4A—C12A—C1	118.93 (10)	C44A—C44—H44	119.4
C4A—C12A—C12	120.35 (10)	C52A—C44A—C44	118.93 (12)
C1—C12A—C12	120.72 (10)	C52A—C44A—N45	121.91 (11)
N5—C13—N11	112.22 (10)	C44—C44A—N45	119.16 (12)
N5—C13—H13A	109.2	C44A—N45—C53	110.68 (11)
N11—C13—H13A	109.2	C44A—N45—C46	112.73 (11)
N5—C13—H13B	109.2	C53—N45—C46	107.52 (11)
N11—C13—H13B	109.2	N45—C46—C46A	112.18 (11)
H13A—C13—H13B	107.9	N45—C46—H46A	109.2
C2—C14—C15	113.09 (10)	C46A—C46—H46A	109.2
C2—C14—H14A	109.0	N45—C46—H46B	109.2
C15—C14—H14A	109.0	C46A—C46—H46B	109.2
C2—C14—H14B	109.0	H46A—C46—H46B	107.9
C15—C14—H14B	109.0	C47—C46A—C50A	118.91 (11)
H14A—C14—H14B	107.8	C47—C46A—C46	120.57 (11)
C14—C15—H15A	109.5	C50A—C46A—C46	120.53 (11)
C14—C15—H15B	109.5	C48—C47—C46A	122.37 (12)
H15A—C15—H15B	109.5	C48—C47—H47	118.8
C14—C15—H15C	109.5	C46A—C47—H47	118.8
H15A—C15—H15C	109.5	C47—C48—C49	117.60 (11)
H15B—C15—H15C	109.5	C47—C48—C56	120.87 (12)
C8—C16—C17	112.89 (11)	C49—C48—C56	121.49 (11)
C8—C16—H16A	109.0	C50—C49—C48	121.16 (11)
C17—C16—H16A	109.0	C50—C49—H49	119.4
C8—C16—H16B	109.0	C48—C49—H49	119.4
C17—C16—H16B	109.0	C49—C50—C50A	120.58 (12)
H16A—C16—H16B	107.8	C49—C50—H50	119.7
C16—C17—H17A	109.5	C50A—C50—H50	119.7
C16—C17—H17B	109.5	C50—C50A—C46A	119.36 (11)
H17A—C17—H17B	109.5	C50—C50A—N51	119.17 (11)
C16—C17—H17C	109.5	C46A—C50A—N51	121.45 (11)
H17A—C17—H17C	109.5	C50A—N51—C53	110.78 (11)
H17B—C17—H17C	109.5	C50A—N51—C52	112.62 (10)
C22—C21—C32A	122.24 (13)	C53—N51—C52	107.68 (10)
C22—C21—H21	118.9	N51—C52—C52A	112.16 (10)
C32A—C21—H21	118.9	N51—C52—H52A	109.2
C23—C22—C21	117.54 (13)	C52A—C52—H52A	109.2
C23—C22—C34	119.95 (14)	N51—C52—H52B	109.2
C21—C22—C34	122.50 (15)	C52A—C52—H52B	109.2
C24—C23—C22	121.45 (13)	H52A—C52—H52B	107.9
C24—C23—H23	119.3	C44A—C52A—C41	118.83 (11)
C22—C23—H23	119.3	C44A—C52A—C52	120.32 (11)
C23—C24—C24A	120.64 (13)	C41—C52A—C52	120.84 (11)
C23—C24—H24	119.7	N51—C53—N45	112.11 (10)
C24A—C24—H24	119.7	N51—C53—H53A	109.2
C32A—C24A—C24	119.07 (12)	N45—C53—H53A	109.2
C32A—C24A—N25	121.79 (11)	N51—C53—H53B	109.2
C24—C24A—N25	119.07 (12)	N45—C53—H53B	109.2
C24A—N25—C33	110.47 (10)	H53A—C53—H53B	107.9
C24A—N25—C26	113.28 (10)	C42—C54—C55	113.15 (12)
C33—N25—C26	107.61 (10)	C42—C54—H54A	108.9
N25—C26—C26A	112.38 (10)	C55—C54—H54A	108.9
N25—C26—H26A	109.1	C42—C54—H54B	108.9
C26A—C26—H26A	109.1	C55—C54—H54B	108.9
N25—C26—H26B	109.1	H54A—C54—H54B	107.8
C26A—C26—H26B	109.1	C54—C55—H55A	109.5
H26A—C26—H26B	107.9	C54—C55—H55B	109.5
C27—C26A—C30A	119.04 (10)	H55A—C55—H55B	109.5
C27—C26A—C26	120.53 (10)	C54—C55—H55C	109.5
C30A—C26A—C26	120.42 (10)	H55A—C55—H55C	109.5
C28—C27—C26A	122.08 (11)	H55B—C55—H55C	109.5
C28—C27—H27	119.0	C48—C56—C57	111.91 (11)
C26A—C27—H27	119.0	C48—C56—H56A	109.2
C27—C28—C29	118.14 (11)	C57—C56—H56A	109.2
C27—C28—C36	120.52 (11)	C48—C56—H56B	109.2
C29—C28—C36	121.34 (11)	C57—C56—H56B	109.2
C30—C29—C28	120.64 (11)	H56A—C56—H56B	107.9
C30—C29—H29	119.7	C56—C57—H57A	109.5
C28—C29—H29	119.7	C56—C57—H57B	109.5
C29—C30—C30A	121.02 (11)	H57A—C57—H57B	109.5
C29—C30—H30	119.5	C56—C57—H57C	109.5
C30A—C30—H30	119.5	H57A—C57—H57C	109.5
C30—C30A—C26A	119.05 (11)	H57B—C57—H57C	109.5
C30—C30A—N31	119.33 (11)

C12A—C1—C2—C3	−0.36 (17)	C26—C26A—C30A—N31	4.13 (17)
C12A—C1—C2—C14	179.54 (11)	C30—C30A—N31—C33	−162.12 (10)
C1—C2—C3—C4	1.29 (18)	C26A—C30A—N31—C33	16.40 (14)
C14—C2—C3—C4	−178.61 (11)	C30—C30A—N31—C32	77.19 (13)
C2—C3—C4—C4A	−0.51 (18)	C26A—C30A—N31—C32	−104.29 (12)
C3—C4—C4A—C12A	−1.24 (17)	C30A—N31—C32—C32A	77.82 (13)
C3—C4—C4A—N5	177.06 (10)	C33—N31—C32—C32A	−44.44 (13)
C4—C4A—N5—C13	−161.67 (10)	C24—C24A—C32A—C21	1.83 (18)
C12A—C4A—N5—C13	16.59 (14)	N25—C24A—C32A—C21	−175.24 (11)
C4—C4A—N5—C6	77.76 (13)	C24—C24A—C32A—C32	−178.50 (11)
C12A—C4A—N5—C6	−103.98 (12)	N25—C24A—C32A—C32	4.42 (17)
C4A—N5—C6—C6A	75.37 (12)	C22—C21—C32A—C24A	−0.78 (19)
C13—N5—C6—C6A	−46.83 (12)	C22—C21—C32A—C32	179.55 (12)
N5—C6—C6A—C7	−166.03 (10)	N31—C32—C32A—C24A	10.34 (16)
N5—C6—C6A—C10A	14.70 (15)	N31—C32—C32A—C21	−170.00 (11)
C10A—C6A—C7—C8	−0.35 (16)	C30A—N31—C33—N25	−54.02 (13)
C6—C6A—C7—C8	−179.63 (10)	C32—N31—C33—N25	69.52 (12)
C6A—C7—C8—C9	0.18 (17)	C24A—N25—C33—N31	−54.21 (13)
C6A—C7—C8—C16	179.01 (10)	C26—N25—C33—N31	69.91 (13)
C7—C8—C9—C10	−0.07 (17)	C23—C22—C34—C35	−167.0 (2)
C16—C8—C9—C10	−178.89 (11)	C21—C22—C34—C35	13.7 (3)
C8—C9—C10—C10A	0.13 (18)	C27—C28—C36—C37	−70.72 (17)
C9—C10—C10A—C6A	−0.30 (17)	C29—C28—C36—C37	109.10 (15)
C9—C10—C10A—N11	178.93 (10)	C52A—C41—C42—C43	−0.58 (18)
C7—C6A—C10A—C10	0.40 (16)	C52A—C41—C42—C54	−179.12 (11)
C6—C6A—C10A—C10	179.68 (10)	C41—C42—C43—C44	−0.60 (19)
C7—C6A—C10A—N11	−178.80 (10)	C54—C42—C43—C44	177.92 (12)
C6—C6A—C10A—N11	0.48 (16)	C42—C43—C44—C44A	0.3 (2)
C10—C10A—N11—C13	−161.31 (10)	C43—C44—C44A—C52A	1.13 (18)
C6A—C10A—N11—C13	17.90 (14)	C43—C44—C44A—N45	−178.48 (11)
C10—C10A—N11—C12	78.29 (13)	C52A—C44A—N45—C53	−16.37 (15)
C6A—C10A—N11—C12	−102.51 (12)	C44—C44A—N45—C53	163.23 (11)
C10A—N11—C12—C12A	77.74 (13)	C52A—C44A—N45—C46	104.10 (13)
C13—N11—C12—C12A	−44.44 (13)	C44—C44A—N45—C46	−76.30 (14)
C4—C4A—C12A—C1	2.12 (17)	C44A—N45—C46—C46A	−76.28 (15)
N5—C4A—C12A—C1	−176.12 (10)	C53—N45—C46—C46A	45.99 (15)
C4—C4A—C12A—C12	−177.29 (11)	N45—C46—C46A—C47	167.60 (12)
N5—C4A—C12A—C12	4.46 (17)	N45—C46—C46A—C50A	−12.46 (18)
C2—C1—C12A—C4A	−1.34 (17)	C50A—C46A—C47—C48	0.41 (19)
C2—C1—C12A—C12	178.07 (11)	C46—C46A—C47—C48	−179.65 (12)
N11—C12—C12A—C4A	10.37 (16)	C46A—C47—C48—C49	0.62 (19)
N11—C12—C12A—C1	−169.04 (10)	C46A—C47—C48—C56	−177.06 (12)
C4A—N5—C13—N11	−54.40 (13)	C47—C48—C49—C50	−0.87 (18)
C6—N5—C13—N11	69.23 (12)	C56—C48—C49—C50	176.80 (12)
C10A—N11—C13—N5	−53.41 (12)	C48—C49—C50—C50A	0.08 (19)
C12—N11—C13—N5	69.69 (12)	C49—C50—C50A—C46A	0.98 (18)
C1—C2—C14—C15	−66.52 (16)	C49—C50—C50A—N51	−177.17 (11)
C3—C2—C14—C15	113.37 (14)	C47—C46A—C50A—C50	−1.20 (18)
C7—C8—C16—C17	−79.23 (16)	C46—C46A—C50A—C50	178.86 (11)
C9—C8—C16—C17	99.55 (16)	C47—C46A—C50A—N51	176.90 (11)
C32A—C21—C22—C23	−0.8 (2)	C46—C46A—C50A—N51	−3.05 (18)
C32A—C21—C22—C34	178.57 (14)	C50—C50A—N51—C53	161.37 (11)
C21—C22—C23—C24	1.3 (2)	C46A—C50A—N51—C53	−16.73 (15)
C34—C22—C23—C24	−178.07 (15)	C50—C50A—N51—C52	−77.97 (14)
C22—C23—C24—C24A	−0.3 (2)	C46A—C50A—N51—C52	103.93 (13)
C23—C24—C24A—C32A	−1.35 (19)	C50A—N51—C52—C52A	−76.75 (13)
C23—C24—C24A—N25	175.80 (12)	C53—N51—C52—C52A	45.68 (13)
C32A—C24A—N25—C33	16.64 (15)	C44—C44A—C52A—C41	−2.24 (16)
C24—C24A—N25—C33	−160.44 (11)	N45—C44A—C52A—C41	177.36 (10)
C32A—C24A—N25—C26	−104.17 (13)	C44—C44A—C52A—C52	176.87 (11)
C24—C24A—N25—C26	78.76 (14)	N45—C44A—C52A—C52	−3.53 (16)
C24A—N25—C26—C26A	77.07 (13)	C42—C41—C52A—C44A	2.01 (17)
C33—N25—C26—C26A	−45.34 (14)	C42—C41—C52A—C52	−177.08 (11)
N25—C26—C26A—C27	−168.07 (10)	N51—C52—C52A—C44A	−11.96 (15)
N25—C26—C26A—C30A	11.25 (16)	N51—C52—C52A—C41	167.13 (10)
C30A—C26A—C27—C28	−0.78 (17)	C50A—N51—C53—N45	53.89 (13)
C26—C26A—C27—C28	178.54 (11)	C52—N51—C53—N45	−69.66 (13)
C26A—C27—C28—C29	−0.92 (17)	C44A—N45—C53—N51	53.62 (13)
C26A—C27—C28—C36	178.91 (11)	C46—N45—C53—N51	−69.92 (13)
C27—C28—C29—C30	1.42 (17)	C43—C42—C54—C55	−93.37 (18)
C36—C28—C29—C30	−178.41 (11)	C41—C42—C54—C55	85.11 (17)
C28—C29—C30—C30A	−0.22 (18)	C47—C48—C56—C57	66.88 (16)
C29—C30—C30A—C26A	−1.51 (17)	C49—C48—C56—C57	−110.71 (14)
C29—C30—C30A—N31	177.05 (10)	C32A—C21—C22—C34B	178.57 (14)
C27—C26A—C30A—C30	1.98 (16)	C34B—C22—C23—C24	−178.07 (15)
C26—C26A—C30A—C30	−177.35 (11)	C23—C22—C34B—C35B	133.2 (6)
C27—C26A—C30A—N31	−176.55 (10)

2,8-bis(i-propyl)-6H,12H-5,11-methanodibenzo[bf][1,5]diazocine (alpha3a) top

Crystal data top

C₂₁H₂₆N₂	F(000) = 664
M_r = 306.44	D_x = 1.194 Mg m⁻³
Triclinic, P1	Melting point = 382–383.5 K
a = 7.6347 (11) Å	Mo Kα radiation, λ = 0.71073 Å
b = 15.454 (2) Å	Cell parameters from 11844 reflections
c = 15.936 (2) Å	θ = 2.4–31.2°
α = 66.214 (2)°	µ = 0.07 mm⁻¹
β = 82.257 (2)°	T = 100 K
γ = 85.370 (2)°	Block, colourless
V = 1704.1 (4) Å³	0.45 × 0.45 × 0.41 mm
Z = 4

Data collection top

Bruker Smart APEXII diffractometer	10060 independent reflections
Radiation source: fine-focus sealed tube	6632 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
ω scans	θ_max = 31.3°, θ_min = 1.4°
Absorption correction: multi-scan Bruker SADABS-2008/1	h = −11→10
T_min = 0.724, T_max = 0.970	k = −21→22
19493 measured reflections	l = −22→23

Refinement top

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	Riding
S = 0.99	w = 1/[σ²(F_o²) + (0.0881P)²] where P = (F_o² + 2F_c²)/3
10060 reflections	(Δ/σ)_max = 0.001
453 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.07311 (15)	0.18135 (8)	0.51202 (8)	0.0156 (2)
H1	1.1802 (14)	0.18344 (8)	0.5433 (4)	0.019*
C2	1.04726 (15)	0.25345 (8)	0.42661 (7)	0.0153 (2)
C3	0.89806 (15)	0.24915 (8)	0.38563 (8)	0.0168 (2)
H3	0.8754 (4)	0.2985 (7)	0.3272 (8)	0.020*
C4	0.78310 (16)	0.17490 (8)	0.42817 (8)	0.0170 (2)
H4	0.6794 (15)	0.17314 (8)	0.3981 (4)	0.020*
C4A	0.81220 (15)	0.10221 (8)	0.51347 (7)	0.0150 (2)
N5	0.69118 (13)	0.02557 (7)	0.55410 (6)	0.0163 (2)
C6	0.52139 (15)	0.05358 (8)	0.59377 (8)	0.0174 (2)
H6A	0.4280 (8)	0.0044 (4)	0.60437 (12)	0.021*
H6B	0.4784 (4)	0.1181 (6)	0.5476 (4)	0.021*
C6A	0.53833 (15)	0.06078 (8)	0.68500 (7)	0.0155 (2)
C7	0.40442 (16)	0.10630 (8)	0.72302 (8)	0.0166 (2)
H7	0.2978 (16)	0.1279 (3)	0.6934 (4)	0.020*
C8	0.42036 (16)	0.12133 (8)	0.80229 (8)	0.0182 (2)
C9	0.57672 (17)	0.08886 (9)	0.84355 (8)	0.0211 (3)
H9	0.5936 (3)	0.10016 (18)	0.9001 (8)	0.025*
C10	0.70876 (16)	0.04164 (9)	0.80872 (8)	0.0200 (2)
H10	0.8172 (16)	0.0182 (3)	0.8402 (5)	0.024*
C10A	0.69027 (15)	0.02671 (8)	0.72914 (7)	0.0156 (2)
N11	0.82775 (13)	−0.02506 (6)	0.69644 (6)	0.0173 (2)
C12	0.98669 (15)	0.03125 (8)	0.65123 (8)	0.0180 (2)
H12A	1.0871 (10)	−0.0114 (4)	0.64492 (9)	0.022*
H12B	1.0183 (3)	0.0624 (3)	0.6905 (4)	0.022*
C12A	0.95750 (15)	0.10620 (8)	0.55644 (7)	0.0151 (2)
C13	0.76638 (16)	−0.05407 (8)	0.62862 (8)	0.0194 (3)
H13A	0.8672 (9)	−0.0831 (3)	0.6019 (3)	0.023*
H13B	0.6755 (9)	−0.1028 (5)	0.6602 (3)	0.023*
C14	1.17398 (16)	0.33408 (8)	0.37619 (8)	0.0188 (2)
H14	1.0997 (10)	0.3955 (8)	0.3549 (3)	0.023*
C15	1.27219 (19)	0.32480 (9)	0.28980 (9)	0.0287 (3)
H15A	1.3539 (11)	0.2664 (6)	0.30870 (17)	0.043*
H15B	1.3447 (11)	0.3833 (6)	0.2526 (5)	0.043*
H15C	1.1832 (7)	0.3185 (6)	0.2506 (5)	0.043*
C16	1.30698 (17)	0.34339 (9)	0.43521 (9)	0.0249 (3)
H16A	1.2418 (5)	0.3485 (6)	0.4927 (5)	0.037*
H16B	1.3779 (10)	0.4021 (6)	0.3988 (4)	0.037*
H16C	1.3894 (10)	0.2858 (5)	0.4533 (5)	0.037*
C17	0.27693 (17)	0.16998 (9)	0.84518 (8)	0.0226 (3)
H17	0.3369 (8)	0.2191 (7)	0.8586 (2)	0.027*
C18	0.1929 (2)	0.09871 (11)	0.93771 (10)	0.0420 (4)
H18A	0.1294 (13)	0.0508 (6)	0.92695 (15)	0.063*
H18B	0.1074 (13)	0.1326 (3)	0.9680 (4)	0.063*
H18C	0.2872 (9)	0.0664 (6)	0.9785 (5)	0.063*
C19	0.13328 (18)	0.22195 (9)	0.78375 (10)	0.0310 (3)
H19A	0.1896 (5)	0.2680 (6)	0.7222 (6)	0.047*
H19B	0.0509 (10)	0.2578 (6)	0.8146 (4)	0.047*
H19C	0.0638 (10)	0.1746 (4)	0.7736 (5)	0.047*
C21	0.41616 (15)	0.60603 (8)	0.22648 (8)	0.0161 (2)
H21	0.3123 (15)	0.6361 (4)	0.1948 (5)	0.019*
C22	0.43166 (15)	0.60981 (8)	0.31156 (7)	0.0155 (2)
C23	0.58072 (16)	0.56621 (8)	0.35511 (8)	0.0177 (2)
H23	0.5958 (3)	0.56791 (8)	0.4148 (8)	0.021*
C24	0.70837 (16)	0.52040 (8)	0.31563 (8)	0.0176 (2)
H24	0.8133 (15)	0.4889 (4)	0.3485 (5)	0.021*
C24A	0.69155 (15)	0.51789 (8)	0.23053 (8)	0.0152 (2)
N25	0.82803 (13)	0.46979 (7)	0.19216 (6)	0.0176 (2)
C26	0.98747 (15)	0.52692 (8)	0.15080 (8)	0.0183 (2)
H26A	1.0892 (10)	0.4849 (4)	0.14067 (12)	0.022*
H26B	1.0201 (4)	0.5530 (2)	0.1952 (4)	0.022*
C26A	0.95990 (15)	0.60820 (8)	0.05954 (7)	0.0150 (2)
C27	1.07856 (15)	0.68252 (8)	0.01982 (8)	0.0161 (2)
H27	1.1838 (15)	0.68073 (8)	0.0525 (5)	0.019*
C28	1.05597 (16)	0.75878 (8)	−0.06331 (8)	0.0169 (2)
C29	0.90610 (16)	0.76037 (8)	−0.10648 (8)	0.0199 (2)
H29	0.8847 (3)	0.8144 (8)	−0.1649 (8)	0.024*
C30	0.78836 (16)	0.68759 (8)	−0.06854 (8)	0.0190 (2)
H30	0.6854 (15)	0.69019 (9)	−0.0995 (5)	0.023*
C30A	0.81489 (15)	0.60992 (8)	0.01399 (8)	0.0161 (2)
N31	0.69202 (13)	0.53428 (7)	0.04878 (7)	0.0180 (2)
C32	0.52385 (15)	0.56098 (9)	0.09124 (8)	0.0184 (2)
H32A	0.4289 (9)	0.5143 (4)	0.09876 (10)	0.022*
H32B	0.4828 (4)	0.6272 (6)	0.0484 (4)	0.022*
C32A	0.54345 (15)	0.56092 (8)	0.18522 (7)	0.0158 (2)
C33	0.76510 (16)	0.44951 (8)	0.11923 (8)	0.0203 (3)
H33A	0.6706 (9)	0.4002 (5)	0.1478 (3)	0.024*
H33B	0.8669 (10)	0.4221 (3)	0.0888 (3)	0.024*
C34	0.28606 (16)	0.65882 (8)	0.35280 (8)	0.0190 (2)
H34	0.2479 (5)	0.7202 (8)	0.2998 (7)	0.023*
C35	0.34436 (17)	0.68658 (9)	0.42634 (8)	0.0246 (3)
H35A	0.3686 (11)	0.6272 (5)	0.4826 (5)	0.037*
H35B	0.2470 (9)	0.7265 (6)	0.4448 (5)	0.037*
H35C	0.4562 (11)	0.7244 (6)	0.4006 (3)	0.037*
C36	0.12493 (17)	0.59635 (10)	0.39312 (10)	0.0301 (3)
H36A	0.0842 (8)	0.5805 (6)	0.3441 (4)	0.045*
H36B	0.0277 (9)	0.6309 (4)	0.4165 (6)	0.045*
H36C	0.1576 (4)	0.5368 (6)	0.4451 (6)	0.045*
C37	1.18768 (17)	0.83773 (8)	−0.10973 (8)	0.0207 (3)
H37	1.1156 (10)	0.9006 (9)	−0.1360 (4)	0.025*
C38	1.30744 (18)	0.84771 (9)	−0.04510 (9)	0.0278 (3)
H38A	1.2328 (6)	0.8536 (6)	0.0097 (5)	0.042*
H38B	1.3800 (11)	0.9060 (6)	−0.0790 (3)	0.042*
H38C	1.3888 (10)	0.7901 (6)	−0.0232 (5)	0.042*
C39	1.2992 (2)	0.82465 (10)	−0.19140 (9)	0.0339 (4)
H39A	1.3743 (11)	0.7653 (6)	−0.1681 (2)	0.051*
H39B	1.3772 (12)	0.8803 (6)	−0.2253 (5)	0.051*
H39C	1.2191 (7)	0.8199 (7)	−0.2343 (5)	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0142 (5)	0.0170 (5)	0.0166 (5)	−0.0004 (4)	−0.0007 (4)	−0.0080 (4)
C2	0.0171 (6)	0.0143 (5)	0.0154 (5)	0.0001 (4)	0.0000 (4)	−0.0075 (4)
C3	0.0198 (6)	0.0168 (5)	0.0135 (5)	0.0011 (5)	−0.0013 (4)	−0.0061 (4)
C4	0.0170 (6)	0.0215 (6)	0.0149 (5)	0.0001 (5)	−0.0021 (4)	−0.0098 (5)
C4A	0.0162 (6)	0.0146 (5)	0.0155 (5)	−0.0009 (4)	0.0019 (4)	−0.0086 (4)
N5	0.0161 (5)	0.0174 (4)	0.0165 (5)	−0.0025 (4)	0.0017 (4)	−0.0084 (4)
C6	0.0151 (6)	0.0224 (6)	0.0173 (5)	−0.0024 (5)	0.0004 (4)	−0.0110 (5)
C6A	0.0165 (6)	0.0159 (5)	0.0140 (5)	−0.0029 (4)	0.0006 (4)	−0.0062 (4)
C7	0.0149 (6)	0.0182 (5)	0.0171 (5)	−0.0018 (4)	−0.0002 (4)	−0.0077 (4)
C8	0.0197 (6)	0.0174 (5)	0.0180 (5)	−0.0031 (5)	0.0023 (5)	−0.0084 (5)
C9	0.0240 (6)	0.0249 (6)	0.0173 (5)	−0.0026 (5)	−0.0014 (5)	−0.0112 (5)
C10	0.0189 (6)	0.0247 (6)	0.0160 (5)	−0.0020 (5)	−0.0026 (5)	−0.0073 (5)
C10A	0.0166 (6)	0.0143 (5)	0.0139 (5)	−0.0024 (4)	0.0014 (4)	−0.0039 (4)
N11	0.0170 (5)	0.0164 (4)	0.0159 (5)	0.0008 (4)	0.0011 (4)	−0.0049 (4)
C12	0.0156 (6)	0.0188 (5)	0.0153 (5)	0.0007 (4)	−0.0005 (4)	−0.0029 (4)
C12A	0.0160 (6)	0.0150 (5)	0.0143 (5)	0.0013 (4)	−0.0002 (4)	−0.0067 (4)
C13	0.0227 (6)	0.0150 (5)	0.0196 (6)	−0.0017 (5)	0.0026 (5)	−0.0073 (5)
C14	0.0209 (6)	0.0144 (5)	0.0190 (6)	−0.0013 (5)	0.0006 (5)	−0.0053 (4)
C15	0.0347 (8)	0.0272 (6)	0.0220 (6)	−0.0110 (6)	0.0082 (6)	−0.0092 (5)
C16	0.0237 (7)	0.0232 (6)	0.0284 (7)	−0.0067 (5)	−0.0007 (5)	−0.0104 (5)
C17	0.0250 (7)	0.0223 (6)	0.0238 (6)	0.0003 (5)	0.0011 (5)	−0.0141 (5)
C18	0.0474 (10)	0.0404 (8)	0.0265 (7)	0.0129 (7)	0.0141 (7)	−0.0094 (6)
C19	0.0299 (8)	0.0288 (7)	0.0339 (7)	0.0061 (6)	0.0016 (6)	−0.0149 (6)
C21	0.0145 (6)	0.0185 (5)	0.0157 (5)	−0.0009 (4)	−0.0012 (4)	−0.0073 (4)
C22	0.0169 (6)	0.0145 (5)	0.0156 (5)	−0.0022 (4)	0.0008 (4)	−0.0070 (4)
C23	0.0197 (6)	0.0197 (5)	0.0148 (5)	−0.0026 (5)	−0.0008 (4)	−0.0079 (4)
C24	0.0161 (6)	0.0188 (5)	0.0162 (5)	−0.0007 (5)	−0.0011 (4)	−0.0053 (4)
C24A	0.0147 (5)	0.0138 (5)	0.0158 (5)	−0.0011 (4)	0.0025 (4)	−0.0059 (4)
N25	0.0174 (5)	0.0169 (5)	0.0168 (5)	0.0001 (4)	0.0031 (4)	−0.0066 (4)
C26	0.0159 (6)	0.0182 (5)	0.0168 (5)	0.0005 (5)	0.0010 (4)	−0.0039 (4)
C26A	0.0157 (6)	0.0162 (5)	0.0130 (5)	0.0011 (4)	0.0006 (4)	−0.0066 (4)
C27	0.0166 (6)	0.0177 (5)	0.0154 (5)	−0.0010 (4)	−0.0011 (4)	−0.0082 (4)
C28	0.0199 (6)	0.0155 (5)	0.0160 (5)	−0.0005 (4)	0.0011 (4)	−0.0080 (4)
C29	0.0239 (6)	0.0201 (6)	0.0139 (5)	0.0019 (5)	−0.0027 (5)	−0.0052 (5)
C30	0.0185 (6)	0.0246 (6)	0.0156 (5)	−0.0009 (5)	−0.0031 (4)	−0.0092 (5)
C30A	0.0172 (6)	0.0180 (5)	0.0153 (5)	−0.0015 (4)	0.0014 (4)	−0.0097 (4)
N31	0.0176 (5)	0.0210 (5)	0.0179 (5)	−0.0037 (4)	0.0025 (4)	−0.0111 (4)
C32	0.0158 (6)	0.0249 (6)	0.0177 (5)	−0.0023 (5)	0.0011 (4)	−0.0124 (5)
C32A	0.0156 (6)	0.0177 (5)	0.0153 (5)	−0.0033 (4)	0.0012 (4)	−0.0084 (4)
C33	0.0236 (6)	0.0169 (5)	0.0218 (6)	−0.0024 (5)	0.0038 (5)	−0.0106 (5)
C34	0.0205 (6)	0.0194 (5)	0.0176 (5)	0.0024 (5)	0.0006 (5)	−0.0093 (5)
C35	0.0301 (7)	0.0236 (6)	0.0241 (6)	0.0001 (5)	0.0012 (5)	−0.0150 (5)
C36	0.0206 (7)	0.0358 (7)	0.0395 (8)	−0.0027 (6)	0.0056 (6)	−0.0231 (6)
C37	0.0250 (7)	0.0155 (5)	0.0207 (6)	−0.0026 (5)	0.0007 (5)	−0.0069 (5)
C38	0.0293 (7)	0.0248 (6)	0.0302 (7)	−0.0094 (6)	−0.0013 (6)	−0.0108 (6)
C39	0.0419 (9)	0.0319 (7)	0.0276 (7)	−0.0167 (7)	0.0145 (6)	−0.0141 (6)

Geometric parameters (Å, º) top

C1—C2	1.3953 (16)	C21—C32A	1.3967 (15)
C1—C12A	1.4010 (15)	C21—C22	1.4014 (15)
C1—H1	1.0225	C21—H21	0.9795
C2—C3	1.4057 (16)	C22—C23	1.3938 (17)
C2—C14	1.5204 (15)	C22—C34	1.5198 (15)
C3—C4	1.3861 (16)	C23—C24	1.3892 (15)
C3—H3	0.9637	C23—H23	0.9839
C4—C4A	1.4030 (16)	C24—C24A	1.3954 (15)
C4—H4	0.9867	C24—H24	0.9987
C4A—C12A	1.3976 (16)	C24A—C32A	1.3977 (17)
C4A—N5	1.4397 (14)	C24A—N25	1.4430 (14)
N5—C13	1.4648 (15)	N25—C33	1.4656 (15)
N5—C6	1.4754 (14)	N25—C26	1.4778 (14)
C6—C6A	1.5252 (15)	C26—C26A	1.5176 (16)
C6—H6A	1.0319	C26—H26A	1.0095
C6—H6B	1.0319	C26—H26B	1.0095
C6A—C10A	1.3929 (17)	C26A—C30A	1.3962 (16)
C6A—C7	1.4029 (15)	C26A—C27	1.4028 (15)
C7—C8	1.3954 (16)	C27—C28	1.3939 (16)
C7—H7	0.9643	C27—H27	1.0075
C8—C9	1.3993 (17)	C28—C29	1.4061 (17)
C8—C17	1.5204 (16)	C28—C37	1.5220 (16)
C9—C10	1.3834 (16)	C29—C30	1.3809 (16)
C9—H9	1.0103	C29—H29	0.9910
C10—C10A	1.4039 (16)	C30—C30A	1.4039 (16)
C10—H10	0.9921	C30—H30	0.9732
C10A—N11	1.4377 (14)	C30A—N31	1.4380 (14)
N11—C13	1.4661 (15)	N31—C33	1.4671 (16)
N11—C12	1.4758 (14)	N31—C32	1.4772 (14)
C12—C12A	1.5201 (16)	C32—C32A	1.5247 (15)
C12—H12A	0.9920	C32—H32A	1.0260
C12—H12B	0.9920	C32—H32B	1.0260
C13—H13A	0.9932	C33—H33A	1.0144
C13—H13B	0.9932	C33—H33B	1.0144
C14—C16	1.5252 (18)	C34—C35	1.5273 (16)
C14—C15	1.5304 (16)	C34—C36	1.5286 (17)
C14—H14	1.0213	C34—H34	1.0365
C15—H15A	1.0172	C35—H35A	1.0162
C15—H15B	1.0172	C35—H35B	1.0162
C15—H15C	1.0172	C35—H35C	1.0162
C16—H16A	1.0109	C36—H36A	0.9991
C16—H16B	1.0109	C36—H36B	0.9991
C16—H16C	1.0109	C36—H36C	0.9991
C17—C19	1.5230 (19)	C37—C38	1.5249 (18)
C17—C18	1.5324 (18)	C37—C39	1.5313 (17)
C17—H17	1.0228	C37—H37	1.0344
C18—H18A	0.9980	C38—H38A	1.0091
C18—H18B	0.9980	C38—H38B	1.0091
C18—H18C	0.9980	C38—H38C	1.0091
C19—H19A	1.0125	C39—H39A	1.0033
C19—H19B	1.0125	C39—H39B	1.0033
C19—H19C	1.0125	C39—H39C	1.0033

C2—C1—C12A	122.33 (11)	C32A—C21—C22	122.40 (11)
C2—C1—H1	118.8	C32A—C21—H21	118.8
C12A—C1—H1	118.8	C22—C21—H21	118.8
C1—C2—C3	117.57 (10)	C23—C22—C21	117.51 (10)
C1—C2—C14	123.05 (11)	C23—C22—C34	123.16 (10)
C3—C2—C14	119.37 (10)	C21—C22—C34	119.32 (11)
C4—C3—C2	120.90 (11)	C24—C23—C22	121.05 (11)
C4—C3—H3	119.5	C24—C23—H23	119.5
C2—C3—H3	119.5	C22—C23—H23	119.5
C3—C4—C4A	120.87 (11)	C23—C24—C24A	120.70 (11)
C3—C4—H4	119.6	C23—C24—H24	119.6
C4A—C4—H4	119.6	C24A—C24—H24	119.6
C12A—C4A—C4	119.17 (10)	C24—C24A—C32A	119.56 (10)
C12A—C4A—N5	121.95 (10)	C24—C24A—N25	118.64 (11)
C4—C4A—N5	118.88 (10)	C32A—C24A—N25	121.80 (10)
C4A—N5—C13	110.74 (9)	C24A—N25—C33	110.70 (9)
C4A—N5—C6	112.28 (8)	C24A—N25—C26	112.13 (9)
C13—N5—C6	107.29 (9)	C33—N25—C26	107.16 (9)
N5—C6—C6A	111.70 (10)	N25—C26—C26A	112.22 (10)
N5—C6—H6A	109.3	N25—C26—H26A	109.2
C6A—C6—H6A	109.3	C26A—C26—H26A	109.2
N5—C6—H6B	109.3	N25—C26—H26B	109.2
C6A—C6—H6B	109.3	C26A—C26—H26B	109.2
H6A—C6—H6B	107.9	H26A—C26—H26B	107.9
C10A—C6A—C7	119.15 (10)	C30A—C26A—C27	119.04 (10)
C10A—C6A—C6	120.60 (10)	C30A—C26A—C26	120.13 (10)
C7—C6A—C6	120.17 (11)	C27—C26A—C26	120.83 (10)
C8—C7—C6A	122.21 (12)	C28—C27—C26A	122.30 (11)
C8—C7—H7	118.9	C28—C27—H27	118.9
C6A—C7—H7	118.9	C26A—C27—H27	118.9
C7—C8—C9	117.33 (11)	C27—C28—C29	117.61 (10)
C7—C8—C17	123.26 (11)	C27—C28—C37	123.06 (11)
C9—C8—C17	119.40 (10)	C29—C28—C37	119.31 (10)
C10—C9—C8	121.54 (11)	C30—C29—C28	120.84 (11)
C10—C9—H9	119.2	C30—C29—H29	119.6
C8—C9—H9	119.2	C28—C29—H29	119.6
C9—C10—C10A	120.39 (12)	C29—C30—C30A	121.05 (11)
C9—C10—H10	119.8	C29—C30—H30	119.5
C10A—C10—H10	119.8	C30A—C30—H30	119.5
C6A—C10A—C10	119.33 (10)	C26A—C30A—C30	119.11 (10)
C6A—C10A—N11	121.77 (10)	C26A—C30A—N31	122.02 (10)
C10—C10A—N11	118.89 (11)	C30—C30A—N31	118.86 (10)
C10A—N11—C13	110.71 (9)	C30A—N31—C33	110.96 (9)
C10A—N11—C12	112.46 (9)	C30A—N31—C32	111.51 (9)
C13—N11—C12	107.12 (9)	C33—N31—C32	107.65 (9)
N11—C12—C12A	111.76 (10)	N31—C32—C32A	111.61 (10)
N11—C12—H12A	109.3	N31—C32—H32A	109.3
C12A—C12—H12A	109.3	C32A—C32—H32A	109.3
N11—C12—H12B	109.3	N31—C32—H32B	109.3
C12A—C12—H12B	109.3	C32A—C32—H32B	109.3
H12A—C12—H12B	107.9	H32A—C32—H32B	108.0
C4A—C12A—C1	119.14 (10)	C21—C32A—C24A	118.77 (10)
C4A—C12A—C12	120.29 (10)	C21—C32A—C32	120.64 (11)
C1—C12A—C12	120.55 (10)	C24A—C32A—C32	120.57 (10)
N5—C13—N11	112.21 (9)	N25—C33—N31	112.23 (9)
N5—C13—H13A	109.2	N25—C33—H33A	109.2
N11—C13—H13A	109.2	N31—C33—H33A	109.2
N5—C13—H13B	109.2	N25—C33—H33B	109.2
N11—C13—H13B	109.2	N31—C33—H33B	109.2
H13A—C13—H13B	107.9	H33A—C33—H33B	107.9
C2—C14—C16	114.40 (10)	C22—C34—C35	113.48 (10)
C2—C14—C15	110.40 (9)	C22—C34—C36	110.28 (9)
C16—C14—C15	109.64 (10)	C35—C34—C36	109.70 (10)
C2—C14—H14	107.4	C22—C34—H34	107.7
C16—C14—H14	107.4	C35—C34—H34	107.7
C15—C14—H14	107.4	C36—C34—H34	107.7
C14—C15—H15A	109.5	C34—C35—H35A	109.5
C14—C15—H15B	109.5	C34—C35—H35B	109.5
H15A—C15—H15B	109.5	H35A—C35—H35B	109.5
C14—C15—H15C	109.5	C34—C35—H35C	109.5
H15A—C15—H15C	109.5	H35A—C35—H35C	109.5
H15B—C15—H15C	109.5	H35B—C35—H35C	109.5
C14—C16—H16A	109.5	C34—C36—H36A	109.5
C14—C16—H16B	109.5	C34—C36—H36B	109.5
H16A—C16—H16B	109.5	H36A—C36—H36B	109.5
C14—C16—H16C	109.5	C34—C36—H36C	109.5
H16A—C16—H16C	109.5	H36A—C36—H36C	109.5
H16B—C16—H16C	109.5	H36B—C36—H36C	109.5
C8—C17—C19	114.66 (10)	C28—C37—C38	114.37 (10)
C8—C17—C18	110.28 (10)	C28—C37—C39	110.03 (9)
C19—C17—C18	109.77 (11)	C38—C37—C39	110.16 (11)
C8—C17—H17	107.3	C28—C37—H37	107.3
C19—C17—H17	107.3	C38—C37—H37	107.3
C18—C17—H17	107.3	C39—C37—H37	107.3
C17—C18—H18A	109.5	C37—C38—H38A	109.5
C17—C18—H18B	109.5	C37—C38—H38B	109.5
H18A—C18—H18B	109.5	H38A—C38—H38B	109.5
C17—C18—H18C	109.5	C37—C38—H38C	109.5
H18A—C18—H18C	109.5	H38A—C38—H38C	109.5
H18B—C18—H18C	109.5	H38B—C38—H38C	109.5
C17—C19—H19A	109.5	C37—C39—H39A	109.5
C17—C19—H19B	109.5	C37—C39—H39B	109.5
H19A—C19—H19B	109.5	H39A—C39—H39B	109.5
C17—C19—H19C	109.5	C37—C39—H39C	109.5
H19A—C19—H19C	109.5	H39A—C39—H39C	109.5
H19B—C19—H19C	109.5	H39B—C39—H39C	109.5

2,8-bis(i-propyl)-6H,12H-5,11-methanodibenzo[bf][1,5]diazocine (beta3a) top

Crystal data top

C₂₁H₂₆N₂	D_x = 1.181 Mg m⁻³
M_r = 306.44	Melting point = 384.5–385.5 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.9437 (17) Å	Cell parameters from 7264 reflections
b = 33.259 (4) Å	θ = 2.3–30.3°
c = 10.7536 (12) Å	µ = 0.07 mm⁻¹
β = 104.713 (2)°	T = 100 K
V = 5169.4 (10) Å³	Needle, colourless
Z = 12	0.48 × 0.18 × 0.10 mm
F(000) = 1992

Data collection top

Bruker Smart 1000 diffractometer	12803 independent reflections
Radiation source: fine-focus sealed tube	9089 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 28.3°, θ_min = 1.2°
Absorption correction: multi-scan Bruker SADABS-2008/1	h = −19→19
T_min = 0.680, T_max = 0.746	k = −44→44
47709 measured reflections	l = −14→14

Refinement top

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0387P)² + 2.490P] where P = (F_o² + 2F_c²)/3
12803 reflections	(Δ/σ)_max = 0.001
679 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.00679 (12)	0.12519 (6)	0.64519 (17)	0.0162 (4)
H1	−0.0033 (2)	0.1540 (6)	0.6504 (2)	0.019*
C2	−0.05178 (12)	0.10316 (6)	0.54716 (17)	0.0159 (4)
C3	−0.03633 (12)	0.06191 (6)	0.54286 (17)	0.0173 (4)
H3	−0.0763 (9)	0.0459 (4)	0.4767 (14)	0.021*
C4	0.03522 (12)	0.04357 (6)	0.63168 (17)	0.0166 (4)
H4	0.0446 (2)	0.0160 (6)	0.6265 (2)	0.020*
C4A	0.09348 (12)	0.06589 (5)	0.72885 (16)	0.0156 (4)
N5	0.16587 (10)	0.04521 (5)	0.82011 (14)	0.0168 (3)
C6	0.24686 (12)	0.03693 (6)	0.76926 (18)	0.0180 (4)
H6A	0.2250 (3)	0.02685 (16)	0.6786 (13)	0.022*
H6B	0.2850 (5)	0.0151 (3)	0.8220 (7)	0.022*
C6A	0.30689 (12)	0.07363 (6)	0.77080 (16)	0.0163 (4)
C7	0.37682 (12)	0.07340 (6)	0.70551 (17)	0.0174 (4)
H7	0.3870 (2)	0.0486 (5)	0.6599 (10)	0.021*
C8	0.43223 (13)	0.10653 (6)	0.70237 (18)	0.0198 (4)
C9	0.41600 (13)	0.14110 (6)	0.7668 (2)	0.0247 (4)
H9	0.4544 (9)	0.1657 (6)	0.7652 (2)	0.030*
C10	0.34764 (13)	0.14207 (6)	0.83318 (19)	0.0232 (4)
H10	0.3373 (3)	0.1671 (6)	0.8783 (10)	0.028*
C10A	0.29336 (12)	0.10832 (6)	0.83704 (17)	0.0174 (4)
N11	0.22538 (11)	0.10988 (5)	0.91060 (14)	0.0187 (3)
C12	0.14150 (13)	0.13197 (6)	0.84214 (17)	0.0181 (4)
H12A	0.1601 (3)	0.1567 (4)	0.8046 (6)	0.022*
H12B	0.1063 (5)	0.13999 (13)	0.9044 (9)	0.022*
C12A	0.07947 (12)	0.10725 (5)	0.73627 (17)	0.0156 (4)
C13	0.19722 (13)	0.06918 (6)	0.93783 (17)	0.0199 (4)
H13A	0.2508 (8)	0.0553 (2)	0.9975 (9)	0.024*
H13B	0.1459 (7)	0.07107 (6)	0.9822 (7)	0.024*
C14	−0.13258 (12)	0.12347 (6)	0.45429 (17)	0.0181 (4)
H14	−0.1179 (3)	0.1526 (6)	0.45225 (18)	0.022*
C15	−0.14995 (14)	0.10732 (6)	0.31701 (17)	0.0234 (4)
H15A	−0.0920 (8)	0.1102 (4)	0.2863 (6)	0.035*
H15B	−0.2016 (9)	0.1230 (3)	0.2588 (8)	0.035*
H15C	−0.1677 (10)	0.0781 (4)	0.3156 (3)	0.035*
C16	−0.21993 (13)	0.11944 (6)	0.50309 (19)	0.0227 (4)
H16A	−0.2369 (6)	0.0905 (4)	0.5046 (12)	0.034*
H16B	−0.2716 (7)	0.1344 (4)	0.4449 (10)	0.034*
H16C	−0.2080 (3)	0.1307 (4)	0.5915 (12)	0.034*
C17	0.50905 (13)	0.10493 (6)	0.63359 (19)	0.0233 (4)
H17	0.5021 (2)	0.0790 (6)	0.5832 (12)	0.028*
C18	0.60389 (14)	0.10425 (8)	0.7307 (2)	0.0361 (6)
H18A	0.6138 (5)	0.1301 (4)	0.7794 (13)	0.054*
H18B	0.6533 (7)	0.1008 (5)	0.6841 (7)	0.054*
H18C	0.6064 (4)	0.0814 (4)	0.7918 (13)	0.054*
C19	0.50414 (14)	0.13947 (7)	0.5389 (2)	0.0288 (5)
H19A	0.4393 (9)	0.1396 (3)	0.4733 (12)	0.043*
H19B	0.5554 (9)	0.1358 (2)	0.4896 (12)	0.043*
H19C	0.5144 (10)	0.1667 (4)	0.5888 (7)	0.043*
C21	0.00073 (12)	0.45710 (6)	0.64925 (16)	0.0158 (4)
H21	−0.0153 (4)	0.4852 (6)	0.6593 (3)	0.019*
C22	−0.05159 (12)	0.43524 (5)	0.54537 (17)	0.0159 (4)
C23	−0.02699 (12)	0.39521 (6)	0.53344 (17)	0.0171 (4)
H23	−0.0614 (8)	0.3795 (3)	0.4625 (15)	0.021*
C24	0.04624 (12)	0.37779 (6)	0.62230 (17)	0.0167 (4)
H24	0.0617 (4)	0.3503 (6)	0.6124 (3)	0.020*
C24A	0.09753 (12)	0.39987 (5)	0.72580 (16)	0.0146 (3)
N25	0.17133 (10)	0.38013 (5)	0.81738 (14)	0.0166 (3)
C26	0.25636 (12)	0.37683 (6)	0.77168 (18)	0.0182 (4)
H26A	0.2391 (3)	0.36915 (13)	0.6791 (13)	0.022*
H26B	0.2959 (6)	0.3550 (3)	0.8203 (7)	0.022*
C26A	0.31165 (12)	0.41555 (5)	0.78763 (17)	0.0166 (4)
C27	0.38597 (12)	0.41994 (6)	0.73141 (18)	0.0181 (4)
H27	0.4024 (4)	0.3974 (5)	0.6830 (11)	0.022*
C28	0.43710 (12)	0.45525 (6)	0.74210 (18)	0.0186 (4)
C29	0.41199 (13)	0.48685 (6)	0.81169 (19)	0.0227 (4)
H29	0.4469 (8)	0.5126 (6)	0.8200 (3)	0.027*
C30	0.33929 (13)	0.48303 (6)	0.86955 (18)	0.0213 (4)
H30	0.3231 (4)	0.5058 (5)	0.9188 (11)	0.026*
C30A	0.28915 (12)	0.44749 (6)	0.85867 (17)	0.0172 (4)
N31	0.21600 (10)	0.44422 (5)	0.92271 (14)	0.0170 (3)
C32	0.13044 (12)	0.46466 (6)	0.85213 (16)	0.0164 (4)
H32A	0.1469 (3)	0.4910 (4)	0.8199 (5)	0.020*
H32B	0.0911 (6)	0.47008 (10)	0.9124 (8)	0.020*
C32A	0.07513 (12)	0.44017 (5)	0.73920 (16)	0.0150 (4)
C33	0.19375 (13)	0.40204 (6)	0.93942 (17)	0.0183 (4)
H33A	0.2477 (8)	0.3889 (2)	1.0000 (9)	0.022*
H33B	0.1399 (8)	0.40062 (6)	0.9786 (6)	0.022*
C34	−0.13448 (12)	0.45449 (6)	0.45306 (17)	0.0177 (4)
H34	−0.1199 (3)	0.4832 (6)	0.4451 (2)	0.021*
C35	−0.15635 (14)	0.43613 (6)	0.31872 (17)	0.0233 (4)
H35A	−0.0994 (7)	0.4374 (4)	0.2842 (7)	0.035*
H35B	−0.2084 (9)	0.4517 (3)	0.2598 (8)	0.035*
H35C	−0.1758 (9)	0.4071 (4)	0.3230 (3)	0.035*
C36	−0.21931 (13)	0.45221 (7)	0.50836 (18)	0.0238 (4)
H36A	−0.2368 (6)	0.4236 (4)	0.5149 (12)	0.036*
H36B	−0.2718 (7)	0.4669 (4)	0.4508 (10)	0.036*
H36C	−0.2044 (4)	0.4647 (4)	0.5953 (12)	0.036*
C37	0.52006 (13)	0.45965 (6)	0.68626 (18)	0.0215 (4)
H37	0.5353 (4)	0.4893 (6)	0.68673 (18)	0.026*
C38	0.60426 (14)	0.43837 (7)	0.7713 (2)	0.0313 (5)
H38A	0.6165 (7)	0.4491 (4)	0.8613 (13)	0.047*
H38B	0.6596 (8)	0.4433 (4)	0.7368 (10)	0.047*
H38C	0.5919 (4)	0.4087 (4)	0.7718 (12)	0.047*
C39	0.50202 (15)	0.44507 (7)	0.5475 (2)	0.0318 (5)
H39A	0.4892 (11)	0.4148 (4)	0.5440 (3)	0.048*
H39B	0.5589 (8)	0.4508 (4)	0.5135 (7)	0.048*
H39C	0.4458 (10)	0.4599 (4)	0.4919 (8)	0.048*
C41	0.00627 (12)	0.79177 (6)	0.68932 (17)	0.0167 (4)
H41	−0.0074 (3)	0.8198 (6)	0.6970 (2)	0.020*
C42	−0.04820 (12)	0.76963 (6)	0.58814 (17)	0.0169 (4)
C43	−0.02693 (13)	0.72903 (6)	0.57947 (17)	0.0181 (4)
H43	−0.0636 (8)	0.7130 (4)	0.5106 (15)	0.022*
C44	0.04592 (13)	0.71152 (6)	0.66815 (17)	0.0174 (4)
H44	0.0592 (3)	0.6840 (6)	0.6601 (2)	0.021*
C44A	0.10014 (12)	0.73375 (5)	0.76911 (17)	0.0160 (4)
N45	0.17358 (10)	0.71392 (5)	0.86054 (14)	0.0175 (3)
C46	0.25791 (12)	0.70957 (6)	0.81400 (18)	0.0188 (4)
H46A	0.2398 (3)	0.70137 (13)	0.7215 (13)	0.023*
H46B	0.2971 (6)	0.6877 (3)	0.8636 (7)	0.023*
C46A	0.31449 (12)	0.74793 (6)	0.82720 (17)	0.0172 (4)
C47	0.38872 (13)	0.75116 (6)	0.77033 (18)	0.0188 (4)
H47	0.4032 (3)	0.7285 (5)	0.7219 (11)	0.023*
C48	0.44232 (13)	0.78574 (6)	0.78093 (18)	0.0201 (4)
C49	0.41910 (13)	0.81802 (6)	0.85021 (19)	0.0230 (4)
H49	0.4559 (8)	0.8435 (6)	0.8583 (3)	0.028*
C50	0.34644 (13)	0.81549 (6)	0.90756 (19)	0.0223 (4)
H50	0.3312 (4)	0.8390 (5)	0.9563 (11)	0.027*
C50A	0.29422 (12)	0.78039 (6)	0.89804 (17)	0.0184 (4)
N51	0.22132 (11)	0.77838 (5)	0.96277 (14)	0.0184 (3)
C52	0.13705 (13)	0.79929 (6)	0.89086 (17)	0.0179 (4)
H52A	0.1550 (3)	0.8251 (4)	0.8566 (5)	0.022*
H52B	0.0981 (6)	0.80589 (12)	0.9509 (9)	0.022*
C52A	0.08020 (12)	0.77457 (5)	0.77998 (17)	0.0159 (4)
C53	0.19746 (13)	0.73650 (6)	0.98156 (18)	0.0198 (4)
H53A	0.1430 (8)	0.73587 (6)	1.0220 (6)	0.024*
H53B	0.2520 (8)	0.7230 (2)	1.0434 (9)	0.024*
C54	−0.13115 (13)	0.78917 (6)	0.49652 (17)	0.0193 (4)
H54	−0.1177 (3)	0.8175 (6)	0.4919 (2)	0.023*
C55	−0.15144 (14)	0.77218 (6)	0.36016 (18)	0.0253 (4)
H55A	−0.0950 (8)	0.7747 (4)	0.3268 (7)	0.038*
H55B	−0.2035 (9)	0.7875 (3)	0.3031 (8)	0.038*
H55C	−0.1690 (10)	0.7432 (4)	0.3613 (3)	0.038*
C56	−0.21659 (13)	0.78536 (6)	0.54973 (19)	0.0232 (4)
H56A	−0.2327 (6)	0.7561 (4)	0.5549 (12)	0.035*
H56B	−0.2703 (7)	0.7998 (4)	0.4911 (10)	0.035*
H56C	−0.2031 (4)	0.7977 (4)	0.6383 (12)	0.035*
C57	0.52659 (13)	0.78938 (6)	0.72671 (18)	0.0220 (4)
H57	0.52769 (13)	0.8174 (6)	0.6947 (7)	0.026*
C58	0.61503 (15)	0.78330 (9)	0.8323 (2)	0.0416 (6)
H58A	0.6173 (6)	0.7545 (4)	0.8659 (12)	0.062*
H58B	0.6161 (6)	0.8029 (5)	0.9058 (13)	0.062*
H58C	0.6709 (8)	0.7884 (5)	0.7963 (7)	0.062*
C59	0.52549 (16)	0.76154 (7)	0.6148 (2)	0.0337 (5)
H59A	0.5312 (11)	0.7327 (4)	0.6459 (5)	0.050*
H59B	0.5792 (9)	0.7683 (3)	0.5770 (11)	0.050*
H59C	0.4653 (9)	0.7650 (3)	0.5466 (11)	0.050*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0175 (9)	0.0149 (9)	0.0186 (9)	−0.0003 (7)	0.0090 (7)	−0.0010 (7)
C2	0.0138 (8)	0.0209 (9)	0.0151 (8)	0.0006 (7)	0.0076 (7)	0.0017 (7)
C3	0.0160 (9)	0.0215 (10)	0.0150 (8)	−0.0028 (7)	0.0051 (7)	−0.0033 (7)
C4	0.0182 (9)	0.0140 (9)	0.0198 (9)	−0.0003 (7)	0.0089 (7)	0.0009 (7)
C4A	0.0156 (9)	0.0185 (9)	0.0144 (8)	0.0002 (7)	0.0069 (7)	0.0027 (7)
N5	0.0161 (8)	0.0193 (8)	0.0158 (7)	0.0019 (6)	0.0052 (6)	0.0024 (6)
C6	0.0159 (9)	0.0192 (9)	0.0195 (9)	0.0001 (7)	0.0056 (7)	0.0021 (7)
C6A	0.0141 (8)	0.0197 (9)	0.0141 (8)	0.0018 (7)	0.0018 (7)	0.0040 (7)
C7	0.0152 (9)	0.0203 (9)	0.0158 (9)	0.0033 (7)	0.0023 (7)	0.0020 (7)
C8	0.0156 (9)	0.0217 (10)	0.0205 (9)	0.0008 (7)	0.0015 (7)	0.0050 (8)
C9	0.0188 (10)	0.0222 (10)	0.0324 (11)	−0.0055 (8)	0.0052 (8)	0.0004 (8)
C10	0.0199 (10)	0.0228 (10)	0.0250 (10)	−0.0006 (8)	0.0023 (8)	−0.0044 (8)
C10A	0.0154 (9)	0.0208 (9)	0.0142 (8)	−0.0005 (7)	0.0003 (7)	0.0002 (7)
N11	0.0178 (8)	0.0237 (9)	0.0151 (7)	0.0001 (6)	0.0049 (6)	−0.0022 (6)
C12	0.0187 (9)	0.0194 (9)	0.0170 (9)	0.0003 (7)	0.0058 (7)	−0.0029 (7)
C12A	0.0153 (8)	0.0178 (9)	0.0155 (8)	−0.0016 (7)	0.0073 (7)	−0.0017 (7)
C13	0.0218 (10)	0.0234 (10)	0.0154 (9)	0.0011 (8)	0.0066 (7)	0.0013 (7)
C14	0.0169 (9)	0.0183 (9)	0.0188 (9)	0.0012 (7)	0.0038 (7)	0.0006 (7)
C15	0.0244 (10)	0.0297 (11)	0.0161 (9)	0.0025 (8)	0.0049 (8)	0.0031 (8)
C16	0.0173 (9)	0.0278 (11)	0.0231 (10)	0.0007 (8)	0.0054 (8)	−0.0032 (8)
C17	0.0190 (10)	0.0249 (10)	0.0271 (10)	0.0006 (8)	0.0077 (8)	0.0072 (8)
C18	0.0189 (11)	0.0504 (15)	0.0393 (13)	0.0051 (10)	0.0080 (10)	0.0166 (11)
C19	0.0228 (10)	0.0375 (12)	0.0261 (11)	−0.0013 (9)	0.0064 (9)	0.0091 (9)
C21	0.0159 (9)	0.0171 (9)	0.0163 (8)	−0.0007 (7)	0.0075 (7)	−0.0004 (7)
C22	0.0154 (9)	0.0184 (9)	0.0147 (8)	−0.0024 (7)	0.0056 (7)	0.0013 (7)
C23	0.0171 (9)	0.0202 (9)	0.0144 (8)	−0.0041 (7)	0.0047 (7)	−0.0020 (7)
C24	0.0193 (9)	0.0147 (9)	0.0178 (9)	−0.0012 (7)	0.0080 (7)	0.0007 (7)
C24A	0.0155 (8)	0.0174 (9)	0.0126 (8)	−0.0010 (7)	0.0070 (7)	0.0020 (7)
N25	0.0146 (7)	0.0195 (8)	0.0153 (7)	0.0004 (6)	0.0030 (6)	0.0015 (6)
C26	0.0161 (9)	0.0176 (9)	0.0210 (9)	0.0020 (7)	0.0048 (7)	0.0006 (7)
C26A	0.0149 (9)	0.0171 (9)	0.0163 (9)	0.0006 (7)	0.0013 (7)	0.0018 (7)
C27	0.0151 (9)	0.0192 (9)	0.0190 (9)	0.0026 (7)	0.0022 (7)	−0.0002 (7)
C28	0.0132 (9)	0.0213 (10)	0.0194 (9)	0.0006 (7)	0.0008 (7)	0.0045 (7)
C29	0.0178 (9)	0.0224 (10)	0.0258 (10)	−0.0031 (8)	0.0017 (8)	0.0011 (8)
C30	0.0192 (9)	0.0205 (10)	0.0224 (10)	0.0004 (8)	0.0022 (8)	−0.0025 (8)
C30A	0.0148 (9)	0.0197 (9)	0.0155 (9)	0.0003 (7)	0.0006 (7)	0.0018 (7)
N31	0.0153 (8)	0.0207 (8)	0.0146 (7)	−0.0003 (6)	0.0033 (6)	0.0001 (6)
C32	0.0165 (9)	0.0180 (9)	0.0145 (8)	−0.0001 (7)	0.0040 (7)	−0.0036 (7)
C32A	0.0145 (8)	0.0176 (9)	0.0143 (8)	−0.0020 (7)	0.0060 (7)	−0.0004 (7)
C33	0.0190 (9)	0.0221 (10)	0.0132 (8)	−0.0007 (7)	0.0031 (7)	0.0024 (7)
C34	0.0149 (9)	0.0189 (9)	0.0178 (9)	0.0000 (7)	0.0013 (7)	0.0000 (7)
C35	0.0199 (10)	0.0338 (12)	0.0149 (9)	0.0024 (8)	0.0020 (7)	0.0041 (8)
C36	0.0175 (9)	0.0346 (12)	0.0192 (9)	0.0035 (8)	0.0048 (8)	−0.0030 (8)
C37	0.0158 (9)	0.0232 (10)	0.0245 (10)	−0.0024 (8)	0.0037 (8)	0.0033 (8)
C38	0.0167 (10)	0.0415 (13)	0.0344 (12)	0.0028 (9)	0.0044 (9)	0.0067 (10)
C39	0.0272 (11)	0.0453 (14)	0.0246 (11)	−0.0107 (10)	0.0097 (9)	−0.0025 (10)
C41	0.0184 (9)	0.0156 (9)	0.0182 (9)	0.0001 (7)	0.0085 (7)	−0.0003 (7)
C42	0.0167 (9)	0.0182 (9)	0.0183 (9)	−0.0003 (7)	0.0089 (7)	0.0013 (7)
C43	0.0189 (9)	0.0193 (9)	0.0171 (9)	−0.0044 (7)	0.0060 (7)	−0.0018 (7)
C44	0.0206 (9)	0.0125 (9)	0.0219 (9)	−0.0002 (7)	0.0107 (8)	−0.0006 (7)
C44A	0.0159 (9)	0.0176 (9)	0.0174 (8)	−0.0005 (7)	0.0099 (7)	0.0032 (7)
N45	0.0166 (8)	0.0189 (8)	0.0183 (8)	0.0015 (6)	0.0066 (6)	0.0023 (6)
C46	0.0171 (9)	0.0179 (9)	0.0231 (9)	0.0023 (7)	0.0080 (7)	0.0009 (7)
C46A	0.0142 (9)	0.0203 (9)	0.0169 (9)	0.0010 (7)	0.0033 (7)	0.0024 (7)
C47	0.0173 (9)	0.0198 (10)	0.0189 (9)	0.0023 (7)	0.0040 (7)	0.0030 (7)
C48	0.0165 (9)	0.0240 (10)	0.0191 (9)	0.0006 (7)	0.0033 (7)	0.0058 (8)
C49	0.0190 (9)	0.0199 (10)	0.0296 (11)	−0.0034 (8)	0.0051 (8)	0.0025 (8)
C50	0.0201 (10)	0.0197 (10)	0.0264 (10)	0.0002 (8)	0.0043 (8)	−0.0033 (8)
C50A	0.0159 (9)	0.0220 (10)	0.0167 (9)	0.0011 (7)	0.0030 (7)	0.0018 (7)
N51	0.0176 (8)	0.0198 (8)	0.0188 (8)	0.0009 (6)	0.0063 (6)	0.0008 (6)
C52	0.0186 (9)	0.0178 (9)	0.0180 (9)	0.0014 (7)	0.0059 (7)	−0.0017 (7)
C52A	0.0157 (9)	0.0166 (9)	0.0181 (9)	−0.0009 (7)	0.0093 (7)	−0.0002 (7)
C53	0.0219 (10)	0.0215 (10)	0.0174 (9)	0.0014 (8)	0.0075 (7)	0.0018 (7)
C54	0.0205 (10)	0.0172 (9)	0.0205 (9)	−0.0009 (7)	0.0056 (8)	−0.0005 (7)
C55	0.0257 (11)	0.0302 (11)	0.0200 (10)	0.0017 (9)	0.0058 (8)	0.0008 (8)
C56	0.0185 (10)	0.0269 (11)	0.0243 (10)	0.0013 (8)	0.0054 (8)	−0.0018 (8)
C57	0.0190 (10)	0.0245 (10)	0.0229 (10)	−0.0012 (8)	0.0059 (8)	0.0066 (8)
C58	0.0193 (11)	0.0752 (19)	0.0302 (12)	0.0004 (11)	0.0061 (9)	0.0113 (12)
C59	0.0299 (12)	0.0401 (13)	0.0351 (12)	−0.0061 (10)	0.0159 (10)	−0.0044 (10)

Geometric parameters (Å, º) top

C1—C2	1.395 (2)	C30A—N31	1.437 (2)
C1—C12A	1.398 (3)	N31—C33	1.464 (2)
C1—H1	0.9724	N31—C32	1.476 (2)
C2—C3	1.394 (3)	C32—C32A	1.520 (2)
C2—C14	1.516 (2)	C32—H32A	0.9953
C3—C4	1.382 (3)	C32—H32B	0.9953
C3—H3	0.9652	C33—H33A	0.9995
C4—C4A	1.392 (3)	C33—H33B	0.9995
C4—H4	0.9308	C34—C35	1.525 (3)
C4A—C12A	1.397 (3)	C34—C36	1.533 (3)
C4A—N5	1.438 (2)	C34—H34	0.9888
N5—C13	1.468 (2)	C35—H35A	1.0128
N5—C6	1.475 (2)	C35—H35B	1.0128
C6—C6A	1.512 (3)	C35—H35C	1.0128
C6—H6A	1.0039	C36—H36A	0.9949
C6—H6B	1.0039	C36—H36B	0.9949
C6A—C10A	1.397 (3)	C36—H36C	0.9949
C6A—C7	1.399 (2)	C37—C39	1.526 (3)
C7—C8	1.384 (3)	C37—C38	1.529 (3)
C7—H7	0.9902	C37—H37	1.0115
C8—C9	1.395 (3)	C38—H38A	1.0033
C8—C17	1.516 (3)	C38—H38B	1.0033
C9—C10	1.387 (3)	C38—H38C	1.0033
C9—H9	1.0016	C39—H39A	1.0248
C10—C10A	1.392 (3)	C39—H39B	1.0248
C10—H10	0.9945	C39—H39C	1.0248
C10A—N11	1.438 (2)	C41—C42	1.392 (3)
N11—C13	1.469 (2)	C41—C52A	1.397 (2)
N11—C12	1.478 (2)	C41—H41	0.9631
C12—C12A	1.515 (2)	C42—C43	1.396 (3)
C12—H12A	0.9872	C42—C54	1.520 (3)
C12—H12B	0.9872	C43—C44	1.381 (3)
C13—H13A	1.0026	C43—H43	0.9631
C13—H13B	1.0026	C44—C44A	1.391 (3)
C14—C15	1.530 (3)	C44—H44	0.9465
C14—C16	1.531 (3)	C44A—C52A	1.401 (2)
C14—H14	0.9964	C44A—N45	1.434 (2)
C15—H15A	1.0072	N45—C53	1.466 (2)
C15—H15B	1.0072	N45—C46	1.476 (2)
C15—H15C	1.0072	C46—C46A	1.517 (3)
C16—H16A	0.9952	C46—H46A	1.0005
C16—H16B	0.9952	C46—H46B	1.0005
C16—H16C	0.9952	C46A—C50A	1.398 (3)
C17—C19	1.525 (3)	C46A—C47	1.400 (3)
C17—C18	1.532 (3)	C47—C48	1.390 (3)
C17—H17	1.0100	C47—H47	0.9724
C18—H18A	0.9979	C48—C49	1.400 (3)
C18—H18B	0.9979	C48—C57	1.521 (3)
C18—H18C	0.9979	C49—C50	1.381 (3)
C19—H19A	1.0433	C49—H49	1.0006
C19—H19B	1.0433	C50—C50A	1.394 (3)
C19—H19C	1.0433	C50—H50	1.0000
C21—C32A	1.394 (2)	C50A—N51	1.436 (2)
C21—C22	1.394 (2)	N51—C53	1.464 (2)
C21—H21	0.9757	N51—C52	1.474 (2)
C22—C23	1.395 (3)	C52—C52A	1.518 (2)
C22—C34	1.518 (2)	C52—H52A	0.9969
C23—C24	1.384 (3)	C52—H52B	0.9969
C23—H23	0.9585	C53—H53A	1.0162
C24—C24A	1.390 (2)	C53—H53B	1.0162
C24—H24	0.9543	C54—C55	1.528 (3)
C24A—C32A	1.398 (2)	C54—C56	1.531 (3)
C24A—N25	1.437 (2)	C54—H54	0.9659
N25—C33	1.464 (2)	C55—H55A	1.0002
N25—C26	1.478 (2)	C55—H55B	1.0002
C26—C26A	1.516 (3)	C55—H55C	1.0002
C26—H26A	0.9963	C56—H56A	1.0086
C26—H26B	0.9963	C56—H56B	1.0086
C26A—C30A	1.398 (3)	C56—H56C	1.0086
C26A—C27	1.400 (3)	C57—C59	1.515 (3)
C27—C28	1.390 (3)	C57—C58	1.522 (3)
C27—H27	0.9790	C57—H57	0.9961
C28—C29	1.395 (3)	C58—H58A	1.0211
C28—C37	1.516 (3)	C58—H58B	1.0211
C29—C30	1.388 (3)	C58—H58C	1.0211
C29—H29	0.9952	C59—H59A	1.0130
C30—C30A	1.389 (3)	C59—H59B	1.0130
C30—H30	0.9878	C59—H59C	1.0130

C2—C1—C12A	122.15 (17)	N31—C32—H32B	109.0
C2—C1—H1	118.9	C32A—C32—H32B	109.0
C12A—C1—H1	118.9	H32A—C32—H32B	107.8
C3—C2—C1	117.68 (16)	C21—C32A—C24A	119.05 (16)
C3—C2—C14	121.84 (16)	C21—C32A—C32	120.93 (16)
C1—C2—C14	120.38 (17)	C24A—C32A—C32	120.01 (16)
C4—C3—C2	121.15 (17)	N25—C33—N31	112.00 (14)
C4—C3—H3	119.4	N25—C33—H33A	109.2
C2—C3—H3	119.4	N31—C33—H33A	109.2
C3—C4—C4A	120.68 (17)	N25—C33—H33B	109.2
C3—C4—H4	119.7	N31—C33—H33B	109.2
C4A—C4—H4	119.7	H33A—C33—H33B	107.9
C4—C4A—C12A	119.58 (16)	C22—C34—C35	113.16 (15)
C4—C4A—N5	118.43 (16)	C22—C34—C36	110.07 (15)
C12A—C4A—N5	121.98 (16)	C35—C34—C36	110.38 (15)
C4A—N5—C13	110.42 (14)	C22—C34—H34	107.7
C4A—N5—C6	112.47 (14)	C35—C34—H34	107.7
C13—N5—C6	107.98 (14)	C36—C34—H34	107.7
N5—C6—C6A	112.68 (15)	C34—C35—H35A	109.5
N5—C6—H6A	109.1	C34—C35—H35B	109.5
C6A—C6—H6A	109.1	H35A—C35—H35B	109.5
N5—C6—H6B	109.1	C34—C35—H35C	109.5
C6A—C6—H6B	109.1	H35A—C35—H35C	109.5
H6A—C6—H6B	107.8	H35B—C35—H35C	109.5
C10A—C6A—C7	118.92 (17)	C34—C36—H36A	109.5
C10A—C6A—C6	120.65 (16)	C34—C36—H36B	109.5
C7—C6A—C6	120.43 (17)	H36A—C36—H36B	109.5
C8—C7—C6A	122.38 (18)	C34—C36—H36C	109.5
C8—C7—H7	118.8	H36A—C36—H36C	109.5
C6A—C7—H7	118.8	H36B—C36—H36C	109.5
C7—C8—C9	117.61 (18)	C28—C37—C39	113.42 (16)
C7—C8—C17	121.04 (18)	C28—C37—C38	110.49 (16)
C9—C8—C17	121.33 (18)	C39—C37—C38	110.61 (18)
C10—C9—C8	121.21 (19)	C28—C37—H37	107.3
C10—C9—H9	119.4	C39—C37—H37	107.3
C8—C9—H9	119.4	C38—C37—H37	107.3
C9—C10—C10A	120.51 (19)	C37—C38—H38A	109.5
C9—C10—H10	119.7	C37—C38—H38B	109.5
C10A—C10—H10	119.7	H38A—C38—H38B	109.5
C10—C10A—C6A	119.33 (17)	C37—C38—H38C	109.5
C10—C10A—N11	119.06 (17)	H38A—C38—H38C	109.5
C6A—C10A—N11	121.60 (17)	H38B—C38—H38C	109.5
C10A—N11—C13	110.77 (15)	C37—C39—H39A	109.5
C10A—N11—C12	111.84 (14)	C37—C39—H39B	109.5
C13—N11—C12	107.92 (14)	H39A—C39—H39B	109.5
N11—C12—C12A	112.60 (15)	C37—C39—H39C	109.5
N11—C12—H12A	109.1	H39A—C39—H39C	109.5
C12A—C12—H12A	109.1	H39B—C39—H39C	109.5
N11—C12—H12B	109.1	C42—C41—C52A	122.05 (17)
C12A—C12—H12B	109.1	C42—C41—H41	119.0
H12A—C12—H12B	107.8	C52A—C41—H41	119.0
C4A—C12A—C1	118.77 (16)	C41—C42—C43	117.77 (17)
C4A—C12A—C12	120.35 (16)	C41—C42—C54	119.95 (16)
C1—C12A—C12	120.87 (16)	C43—C42—C54	122.17 (17)
N5—C13—N11	111.91 (14)	C44—C43—C42	120.98 (17)
N5—C13—H13A	109.2	C44—C43—H43	119.5
N11—C13—H13A	109.2	C42—C43—H43	119.5
N5—C13—H13B	109.2	C43—C44—C44A	121.05 (17)
N11—C13—H13B	109.2	C43—C44—H44	119.5
H13A—C13—H13B	107.9	C44A—C44—H44	119.5
C2—C14—C15	113.00 (16)	C44—C44A—C52A	119.08 (17)
C2—C14—C16	109.92 (15)	C44—C44A—N45	118.90 (16)
C15—C14—C16	110.45 (15)	C52A—C44A—N45	122.01 (16)
C2—C14—H14	107.8	C44A—N45—C53	110.14 (14)
C15—C14—H14	107.8	C44A—N45—C46	112.52 (14)
C16—C14—H14	107.8	C53—N45—C46	108.35 (14)
C14—C15—H15A	109.5	N45—C46—C46A	112.91 (15)
C14—C15—H15B	109.5	N45—C46—H46A	109.0
H15A—C15—H15B	109.5	C46A—C46—H46A	109.0
C14—C15—H15C	109.5	N45—C46—H46B	109.0
H15A—C15—H15C	109.5	C46A—C46—H46B	109.0
H15B—C15—H15C	109.5	H46A—C46—H46B	107.8
C14—C16—H16A	109.5	C50A—C46A—C47	118.95 (17)
C14—C16—H16B	109.5	C50A—C46A—C46	120.50 (16)
H16A—C16—H16B	109.5	C47—C46A—C46	120.54 (17)
C14—C16—H16C	109.5	C48—C47—C46A	122.12 (18)
H16A—C16—H16C	109.5	C48—C47—H47	118.9
H16B—C16—H16C	109.5	C46A—C47—H47	118.9
C8—C17—C19	112.67 (17)	C47—C48—C49	117.57 (18)
C8—C17—C18	110.60 (17)	C47—C48—C57	123.40 (18)
C19—C17—C18	110.21 (17)	C49—C48—C57	118.96 (17)
C8—C17—H17	107.7	C50—C49—C48	121.35 (19)
C19—C17—H17	107.7	C50—C49—H49	119.3
C18—C17—H17	107.7	C48—C49—H49	119.3
C17—C18—H18A	109.5	C49—C50—C50A	120.50 (19)
C17—C18—H18B	109.5	C49—C50—H50	119.8
H18A—C18—H18B	109.5	C50A—C50—H50	119.8
C17—C18—H18C	109.5	C50—C50A—C46A	119.48 (17)
H18A—C18—H18C	109.5	C50—C50A—N51	118.89 (17)
H18B—C18—H18C	109.5	C46A—C50A—N51	121.62 (17)
C17—C19—H19A	109.5	C50A—N51—C53	110.65 (15)
C17—C19—H19B	109.5	C50A—N51—C52	112.08 (14)
H19A—C19—H19B	109.5	C53—N51—C52	108.40 (15)
C17—C19—H19C	109.5	N51—C52—C52A	112.93 (15)
H19A—C19—H19C	109.5	N51—C52—H52A	109.0
H19B—C19—H19C	109.5	C52A—C52—H52A	109.0
C32A—C21—C22	122.10 (17)	N51—C52—H52B	109.0
C32A—C21—H21	118.9	C52A—C52—H52B	109.0
C22—C21—H21	118.9	H52A—C52—H52B	107.8
C21—C22—C23	117.64 (17)	C41—C52A—C44A	119.06 (17)
C21—C22—C34	120.14 (16)	C41—C52A—C52	120.81 (16)
C23—C22—C34	122.17 (16)	C44A—C52A—C52	120.12 (16)
C24—C23—C22	121.09 (17)	N51—C53—N45	112.19 (15)
C24—C23—H23	119.5	N51—C53—H53A	109.2
C22—C23—H23	119.5	N45—C53—H53A	109.2
C23—C24—C24A	120.68 (17)	N51—C53—H53B	109.2
C23—C24—H24	119.7	N45—C53—H53B	109.2
C24A—C24—H24	119.7	H53A—C53—H53B	107.9
C24—C24A—C32A	119.42 (16)	C42—C54—C55	113.23 (16)
C24—C24A—N25	118.59 (16)	C42—C54—C56	110.04 (15)
C32A—C24A—N25	121.98 (16)	C55—C54—C56	110.30 (16)
C24A—N25—C33	110.37 (14)	C42—C54—H54	107.7
C24A—N25—C26	112.39 (14)	C55—C54—H54	107.7
C33—N25—C26	108.34 (14)	C56—C54—H54	107.7
N25—C26—C26A	112.90 (15)	C54—C55—H55A	109.5
N25—C26—H26A	109.0	C54—C55—H55B	109.5
C26A—C26—H26A	109.0	H55A—C55—H55B	109.5
N25—C26—H26B	109.0	C54—C55—H55C	109.5
C26A—C26—H26B	109.0	H55A—C55—H55C	109.5
H26A—C26—H26B	107.8	H55B—C55—H55C	109.5
C30A—C26A—C27	118.93 (17)	C54—C56—H56A	109.5
C30A—C26A—C26	120.48 (16)	C54—C56—H56B	109.5
C27—C26A—C26	120.59 (17)	H56A—C56—H56B	109.5
C28—C27—C26A	122.13 (18)	C54—C56—H56C	109.5
C28—C27—H27	118.9	H56A—C56—H56C	109.5
C26A—C27—H27	118.9	H56B—C56—H56C	109.5
C27—C28—C29	117.62 (18)	C59—C57—C48	114.39 (17)
C27—C28—C37	122.45 (18)	C59—C57—C58	110.12 (19)
C29—C28—C37	119.88 (17)	C48—C57—C58	110.48 (16)
C30—C29—C28	121.28 (19)	C59—C57—H57	107.2
C30—C29—H29	119.4	C48—C57—H57	107.2
C28—C29—H29	119.4	C58—C57—H57	107.2
C29—C30—C30A	120.47 (19)	C57—C58—H58A	109.5
C29—C30—H30	119.8	C57—C58—H58B	109.5
C30A—C30—H30	119.8	H58A—C58—H58B	109.5
C30—C30A—C26A	119.55 (17)	C57—C58—H58C	109.5
C30—C30A—N31	118.95 (17)	H58A—C58—H58C	109.5
C26A—C30A—N31	121.49 (16)	H58B—C58—H58C	109.5
C30A—N31—C33	110.83 (15)	C57—C59—H59A	109.5
C30A—N31—C32	112.57 (14)	C57—C59—H59B	109.5
C33—N31—C32	108.09 (14)	H59A—C59—H59B	109.5
N31—C32—C32A	112.84 (15)	C57—C59—H59C	109.5
N31—C32—H32A	109.0	H59A—C59—H59C	109.5
C32A—C32—H32A	109.0	H59B—C59—H59C	109.5

C12A—C1—C2—C3	0.6 (3)	C26—C26A—C30A—N31	2.5 (3)
C12A—C1—C2—C14	177.04 (16)	C30—C30A—N31—C33	−159.95 (16)
C1—C2—C3—C4	−0.8 (3)	C26A—C30A—N31—C33	19.1 (2)
C14—C2—C3—C4	−177.14 (16)	C30—C30A—N31—C32	78.9 (2)
C2—C3—C4—C4A	0.6 (3)	C26A—C30A—N31—C32	−102.13 (19)
C3—C4—C4A—C12A	−0.2 (3)	C30A—N31—C32—C32A	78.76 (19)
C3—C4—C4A—N5	178.93 (16)	C33—N31—C32—C32A	−43.98 (19)
C4—C4A—N5—C13	−159.52 (16)	C22—C21—C32A—C24A	−0.7 (3)
C12A—C4A—N5—C13	19.5 (2)	C22—C21—C32A—C32	−179.50 (16)
C4—C4A—N5—C6	79.8 (2)	C24—C24A—C32A—C21	1.0 (2)
C12A—C4A—N5—C6	−101.15 (19)	N25—C24A—C32A—C21	−177.85 (16)
C4A—N5—C6—C6A	77.51 (19)	C24—C24A—C32A—C32	179.83 (16)
C13—N5—C6—C6A	−44.58 (19)	N25—C24A—C32A—C32	1.0 (2)
N5—C6—C6A—C10A	11.4 (2)	N31—C32—C32A—C21	−169.49 (15)
N5—C6—C6A—C7	−168.45 (15)	N31—C32—C32A—C24A	11.7 (2)
C10A—C6A—C7—C8	−1.1 (3)	C24A—N25—C33—N31	−55.38 (19)
C6—C6A—C7—C8	178.78 (17)	C26—N25—C33—N31	68.07 (18)
C6A—C7—C8—C9	−0.3 (3)	C30A—N31—C33—N25	−55.03 (19)
C6A—C7—C8—C17	178.40 (17)	C32—N31—C33—N25	68.77 (18)
C7—C8—C9—C10	0.9 (3)	C21—C22—C34—C35	153.52 (17)
C17—C8—C9—C10	−177.88 (18)	C23—C22—C34—C35	−29.1 (2)
C8—C9—C10—C10A	0.0 (3)	C21—C22—C34—C36	−82.5 (2)
C9—C10—C10A—C6A	−1.5 (3)	C23—C22—C34—C36	95.0 (2)
C9—C10—C10A—N11	177.75 (17)	C27—C28—C37—C39	47.9 (3)
C7—C6A—C10A—C10	2.0 (3)	C29—C28—C37—C39	−134.80 (19)
C6—C6A—C10A—C10	−177.88 (17)	C27—C28—C37—C38	−77.0 (2)
C7—C6A—C10A—N11	−177.25 (16)	C29—C28—C37—C38	100.4 (2)
C6—C6A—C10A—N11	2.9 (3)	C52A—C41—C42—C43	0.2 (3)
C10—C10A—N11—C13	−161.62 (16)	C52A—C41—C42—C54	176.54 (16)
C6A—C10A—N11—C13	17.6 (2)	C41—C42—C43—C44	−0.2 (3)
C10—C10A—N11—C12	77.9 (2)	C54—C42—C43—C44	−176.49 (16)
C6A—C10A—N11—C12	−102.84 (19)	C42—C43—C44—C44A	0.2 (3)
C10A—N11—C12—C12A	76.98 (19)	C43—C44—C44A—C52A	−0.2 (3)
C13—N11—C12—C12A	−45.10 (19)	C43—C44—C44A—N45	178.45 (16)
C4—C4A—C12A—C1	0.0 (3)	C44—C44A—N45—C53	−157.78 (16)
N5—C4A—C12A—C1	−179.06 (16)	C52A—C44A—N45—C53	20.8 (2)
C4—C4A—C12A—C12	179.36 (16)	C44—C44A—N45—C46	81.2 (2)
N5—C4A—C12A—C12	0.3 (3)	C52A—C44A—N45—C46	−100.16 (19)
C2—C1—C12A—C4A	−0.2 (3)	C44A—N45—C46—C46A	79.14 (19)
C2—C1—C12A—C12	−179.60 (16)	C53—N45—C46—C46A	−42.9 (2)
N11—C12—C12A—C4A	13.1 (2)	N45—C46—C46A—C50A	10.8 (2)
N11—C12—C12A—C1	−167.51 (15)	N45—C46—C46A—C47	−170.22 (16)
C4A—N5—C13—N11	−54.65 (19)	C50A—C46A—C47—C48	−0.7 (3)
C6—N5—C13—N11	68.69 (19)	C46—C46A—C47—C48	−179.68 (17)
C10A—N11—C13—N5	−53.93 (19)	C46A—C47—C48—C49	−0.6 (3)
C12—N11—C13—N5	68.81 (18)	C46A—C47—C48—C57	176.48 (17)
C3—C2—C14—C15	−40.5 (2)	C47—C48—C49—C50	0.9 (3)
C1—C2—C14—C15	143.25 (17)	C57—C48—C49—C50	−176.36 (18)
C3—C2—C14—C16	83.4 (2)	C48—C49—C50—C50A	0.2 (3)
C1—C2—C14—C16	−92.9 (2)	C49—C50—C50A—C46A	−1.5 (3)
C7—C8—C17—C19	128.3 (2)	C49—C50—C50A—N51	177.81 (17)
C9—C8—C17—C19	−53.0 (3)	C47—C46A—C50A—C50	1.7 (3)
C7—C8—C17—C18	−107.8 (2)	C46—C46A—C50A—C50	−179.24 (17)
C9—C8—C17—C18	70.9 (2)	C47—C46A—C50A—N51	−177.56 (16)
C32A—C21—C22—C23	−0.1 (3)	C46—C46A—C50A—N51	1.5 (3)
C32A—C21—C22—C34	177.44 (16)	C50—C50A—N51—C53	−159.58 (17)
C21—C22—C23—C24	0.6 (3)	C46A—C50A—N51—C53	19.7 (2)
C34—C22—C23—C24	−176.92 (16)	C50—C50A—N51—C52	79.3 (2)
C22—C23—C24—C24A	−0.2 (3)	C46A—C50A—N51—C52	−101.4 (2)
C23—C24—C24A—C32A	−0.6 (3)	C50A—N51—C52—C52A	79.20 (19)
C23—C24—C24A—N25	178.33 (16)	C53—N51—C52—C52A	−43.21 (19)
C24—C24A—N25—C33	−159.01 (16)	C42—C41—C52A—C44A	−0.2 (3)
C32A—C24A—N25—C33	19.9 (2)	C42—C41—C52A—C52	−178.69 (16)
C24—C24A—N25—C26	79.9 (2)	C44—C44A—C52A—C41	0.2 (2)
C32A—C24A—N25—C26	−101.20 (19)	N45—C44A—C52A—C41	−178.45 (15)
C24A—N25—C26—C26A	79.35 (19)	C44—C44A—C52A—C52	178.72 (16)
C33—N25—C26—C26A	−42.87 (19)	N45—C44A—C52A—C52	0.1 (3)
N25—C26—C26A—C30A	10.1 (2)	N51—C52—C52A—C41	−169.87 (15)
N25—C26—C26A—C27	−169.85 (16)	N51—C52—C52A—C44A	11.6 (2)
C30A—C26A—C27—C28	−1.1 (3)	C50A—N51—C53—N45	−55.07 (19)
C26—C26A—C27—C28	178.82 (17)	C52—N51—C53—N45	68.21 (18)
C26A—C27—C28—C29	0.0 (3)	C44A—N45—C53—N51	−55.60 (19)
C26A—C27—C28—C37	177.41 (17)	C46—N45—C53—N51	67.86 (19)
C27—C28—C29—C30	0.8 (3)	C41—C42—C54—C55	149.00 (17)
C37—C28—C29—C30	−176.70 (17)	C43—C42—C54—C55	−34.8 (2)
C28—C29—C30—C30A	−0.4 (3)	C41—C42—C54—C56	−87.1 (2)
C29—C30—C30A—C26A	−0.7 (3)	C43—C42—C54—C56	89.1 (2)
C29—C30—C30A—N31	178.32 (17)	C47—C48—C57—C59	25.2 (3)
C27—C26A—C30A—C30	1.4 (3)	C49—C48—C57—C59	−157.69 (18)
C26—C26A—C30A—C30	−178.49 (17)	C47—C48—C57—C58	−99.7 (2)
C27—C26A—C30A—N31	−177.56 (16)	C49—C48—C57—C58	77.4 (2)

2,8-bis(i-propyl)-6H,12H-5,11-methanodibenzo[bf][1,5]diazocine (gamma3a) top

Crystal data top

C₂₁H₂₆N₂	D_x = 1.168 Mg m⁻³
M_r = 306.44	Melting point = 383.5–384.5 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.985 (3) Å	Cell parameters from 3270 reflections
b = 11.195 (2) Å	θ = 2.3–28.6°
c = 10.7460 (18) Å	µ = 0.07 mm⁻¹
β = 104.873 (2)°	T = 148 K
V = 1742.3 (5) Å³	Needle, colourless
Z = 4	0.69 × 0.22 × 0.10 mm
F(000) = 664

Data collection top

Bruker Smart 1000 diffractometer	5112 independent reflections
Radiation source: fine-focus sealed tube	2968 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 30.4°, θ_min = 1.4°
Absorption correction: multi-scan Bruker SADABS-2008/1	h = −21→21
T_min = 0.623, T_max = 0.746	k = −15→15
17929 measured reflections	l = −14→15

Refinement top

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) = 0.135	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0604P)² + 0.1599P] where P = (F_o² + 2F_c²)/3
5112 reflections	(Δ/σ)_max < 0.001
275 parameters	Δρ_max = 0.21 e Å⁻³
10 restraints	Δρ_min = −0.18 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.3841 (5)	0.2482 (5)	0.7418 (7)	0.0349 (9)	0.571 (3)
H1	0.3981	0.3127	0.6956	0.042*	0.571 (3)
C2	0.4360 (4)	0.1446 (4)	0.7520 (5)	0.0367 (8)	0.571 (3)
C3	0.4127 (4)	0.0493 (5)	0.8205 (5)	0.0421 (9)	0.571 (3)
H3	0.4473	−0.0205	0.8286	0.050*	0.571 (3)
C4	0.3397 (5)	0.0550 (6)	0.8767 (7)	0.0367 (9)	0.571 (3)
H4	0.3234	−0.0115	0.9179	0.044*	0.571 (3)
C4A	0.2905 (9)	0.1618 (9)	0.8709 (9)	0.0293 (11)	0.571 (3)
C12	0.2539 (13)	0.3719 (13)	0.784 (2)	0.0320 (10)	0.571 (3)
H12A	0.2919	0.4356	0.8309	0.038*	0.571 (3)
H12B	0.2368	0.3939	0.6936	0.038*	0.571 (3)
C12A	0.3112 (7)	0.2571 (8)	0.7998 (10)	0.0279 (10)	0.571 (3)
C14	0.5200 (2)	0.1341 (4)	0.6978 (3)	0.0455 (8)	0.571 (3)
H14A	0.5259	0.0499	0.6760	0.055*	0.571 (3)
C15	0.6056 (4)	0.1679 (8)	0.7961 (6)	0.081 (2)	0.571 (3)
H15A	0.6047	0.2520	0.8131	0.097*	0.571 (3)
H15B	0.6585	0.1493	0.7646	0.097*	0.571 (3)
H15C	0.6090	0.1242	0.8741	0.097*	0.571 (3)
C16	0.5125 (3)	0.2069 (5)	0.5757 (4)	0.0908 (18)	0.571 (3)
H16A	0.4583	0.1832	0.5113	0.109*	0.571 (3)
H16B	0.5662	0.1932	0.5443	0.109*	0.571 (3)
H16C	0.5085	0.2903	0.5945	0.109*	0.571 (3)
C1B	0.3742 (8)	0.2807 (8)	0.7205 (10)	0.0349 (9)	0.429 (3)
H1B	0.3859 (8)	0.357 (3)	0.6732 (19)	0.042*	0.429 (3)
C2B	0.4303 (5)	0.1822 (6)	0.7191 (6)	0.0367 (8)	0.429 (3)
C3B	0.4136 (6)	0.0801 (7)	0.7829 (7)	0.0421 (9)	0.429 (3)
H3B	0.4523 (15)	0.003 (3)	0.7806 (7)	0.050*	0.429 (3)
C4B	0.3456 (7)	0.0797 (8)	0.8499 (10)	0.0367 (9)	0.429 (3)
H4B	0.3373 (7)	0.003 (3)	0.905 (2)	0.044*	0.429 (3)
C24A	0.2879 (13)	0.1783 (13)	0.8461 (14)	0.0293 (11)	0.429 (3)
C12B	0.2440 (18)	0.3890 (18)	0.781 (3)	0.0320 (10)	0.429 (3)
H12C	0.2830 (19)	0.455 (2)	0.836 (3)	0.038*	0.429 (3)
H12D	0.2210 (19)	0.4203 (19)	0.688 (4)	0.038*	0.429 (3)
C32A	0.3022 (10)	0.2818 (12)	0.7827 (14)	0.0279 (10)	0.429 (3)
C14B	0.5072 (3)	0.1867 (5)	0.6490 (6)	0.0443 (11)	0.429 (3)
H14B	0.4981	0.2596	0.5968	0.053*	0.429 (3)
C15B	0.5995 (6)	0.1971 (9)	0.7448 (8)	0.081 (3)	0.429 (3)
H15D	0.5999	0.2664	0.7976	0.097*	0.429 (3)
H15E	0.6470	0.2045	0.6999	0.097*	0.429 (3)
H15F	0.6105	0.1271	0.7981	0.097*	0.429 (3)
C16B	0.5042 (3)	0.0836 (4)	0.5593 (4)	0.0562 (12)	0.429 (3)
H16D	0.5498	0.0948	0.5118	0.084*	0.429 (3)
H16E	0.4441	0.0790	0.5005	0.084*	0.429 (3)
H16F	0.5168	0.0109	0.6080	0.084*	0.429 (3)
N5	0.21879 (7)	0.17047 (9)	0.92914 (10)	0.0342 (3)
C6	0.13483 (9)	0.10700 (11)	0.85890 (12)	0.0323 (3)
H6A	0.0969 (4)	0.0860 (2)	0.9209 (6)	0.039*
H6B	0.15314 (19)	0.0302 (7)	0.8233 (3)	0.039*
C6A	0.07616 (8)	0.18015 (10)	0.74930 (11)	0.0266 (3)
C7	0.00284 (8)	0.12823 (11)	0.65871 (11)	0.0273 (3)
H7	−0.00999 (19)	0.0433 (12)	0.66651 (15)	0.033*
C8	−0.05264 (8)	0.19294 (10)	0.55771 (11)	0.0270 (3)
C9	−0.03285 (8)	0.31384 (11)	0.54915 (12)	0.0306 (3)
H9	−0.0712 (5)	0.3624 (7)	0.4777 (10)	0.037*
C10	0.03904 (8)	0.36740 (11)	0.63810 (11)	0.0298 (3)
H10	0.05121 (19)	0.4519 (12)	0.63029 (16)	0.036*
C10A	0.09428 (8)	0.30181 (10)	0.73881 (11)	0.0274 (3)
N11	0.16687 (7)	0.36185 (9)	0.83075 (9)	0.0305 (2)
C13	0.19355 (9)	0.29337 (11)	0.95077 (12)	0.0343 (3)
H13A	0.2476 (5)	0.3338 (4)	1.0117 (6)	0.041*
H13B	0.1405 (5)	0.29261 (11)	0.9926 (4)	0.041*
C17	−0.13430 (8)	0.13383 (12)	0.46514 (12)	0.0312 (3)
H17	−0.1195 (2)	0.0465 (12)	0.46081 (13)	0.037*
C18	−0.15417 (10)	0.18398 (13)	0.32875 (12)	0.0410 (3)
H18A	−0.0969 (5)	0.1781 (8)	0.2965 (4)	0.062*
H18B	−0.1733 (6)	0.2702 (8)	0.32923 (19)	0.062*
H18C	−0.2054 (6)	0.1368 (6)	0.2705 (5)	0.062*
C19	−0.21982 (9)	0.14388 (13)	0.51721 (13)	0.0405 (3)
H19A	−0.2727 (5)	0.0990 (8)	0.4587 (7)	0.061*
H19B	−0.2372 (4)	0.2308 (7)	0.5207 (8)	0.061*
H19C	−0.2060 (2)	0.1085 (8)	0.6066 (8)	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0269 (18)	0.041 (3)	0.035 (2)	0.000 (2)	0.0051 (17)	−0.0037 (18)
C2	0.0306 (10)	0.042 (3)	0.035 (2)	0.0012 (18)	0.0052 (16)	−0.0029 (15)
C3	0.0357 (9)	0.043 (3)	0.045 (3)	0.0113 (16)	0.0065 (18)	−0.0007 (15)
C4	0.0374 (12)	0.031 (3)	0.040 (3)	−0.0001 (16)	0.0075 (14)	0.0084 (15)
C4A	0.0294 (9)	0.038 (3)	0.018 (4)	0.0043 (17)	0.000 (2)	0.0016 (17)
C12	0.029 (3)	0.033 (4)	0.0352 (11)	−0.0021 (19)	0.010 (2)	−0.002 (3)
C12A	0.0243 (19)	0.031 (4)	0.025 (3)	0.0049 (17)	−0.0004 (19)	0.0008 (19)
C14	0.0304 (14)	0.061 (2)	0.0439 (19)	0.0078 (14)	0.0068 (13)	−0.0012 (15)
C15	0.0222 (16)	0.138 (5)	0.080 (4)	−0.002 (2)	0.008 (2)	−0.012 (4)
C16	0.062 (2)	0.156 (5)	0.064 (3)	0.043 (3)	0.033 (2)	0.032 (3)
C1B	0.0269 (18)	0.041 (3)	0.035 (2)	0.000 (2)	0.0051 (17)	−0.0037 (18)
C2B	0.0306 (10)	0.042 (3)	0.035 (2)	0.0012 (18)	0.0052 (16)	−0.0029 (15)
C3B	0.0357 (9)	0.043 (3)	0.045 (3)	0.0113 (16)	0.0065 (18)	−0.0007 (15)
C4B	0.0374 (12)	0.031 (3)	0.040 (3)	−0.0001 (16)	0.0075 (14)	0.0084 (15)
C24A	0.0294 (9)	0.038 (3)	0.018 (4)	0.0043 (17)	0.000 (2)	0.0016 (17)
C12B	0.029 (3)	0.033 (4)	0.0352 (11)	−0.0021 (19)	0.010 (2)	−0.002 (3)
C32A	0.0243 (19)	0.031 (4)	0.025 (3)	0.0049 (17)	−0.0004 (19)	0.0008 (19)
C14B	0.036 (2)	0.049 (3)	0.049 (3)	0.002 (2)	0.015 (2)	−0.016 (2)
C15B	0.055 (4)	0.100 (6)	0.095 (6)	−0.021 (4)	0.034 (4)	−0.053 (5)
C16B	0.048 (2)	0.075 (3)	0.047 (2)	0.000 (2)	0.0152 (17)	−0.020 (2)
N5	0.0349 (6)	0.0375 (6)	0.0280 (5)	0.0021 (5)	0.0037 (5)	−0.0023 (4)
C6	0.0358 (7)	0.0328 (7)	0.0270 (6)	0.0012 (5)	0.0057 (5)	0.0029 (5)
C6A	0.0285 (6)	0.0288 (6)	0.0246 (6)	0.0018 (5)	0.0108 (5)	0.0005 (5)
C7	0.0304 (6)	0.0275 (6)	0.0266 (6)	0.0000 (5)	0.0116 (5)	0.0008 (5)
C8	0.0280 (6)	0.0300 (6)	0.0257 (6)	0.0014 (5)	0.0117 (5)	−0.0010 (5)
C9	0.0334 (6)	0.0311 (6)	0.0276 (6)	0.0044 (5)	0.0083 (5)	0.0032 (5)
C10	0.0356 (7)	0.0260 (6)	0.0295 (6)	−0.0002 (5)	0.0117 (5)	0.0012 (5)
C10A	0.0289 (6)	0.0299 (6)	0.0257 (6)	−0.0010 (5)	0.0114 (5)	−0.0032 (5)
N11	0.0314 (5)	0.0334 (5)	0.0271 (5)	−0.0034 (4)	0.0080 (4)	−0.0034 (4)
C13	0.0379 (7)	0.0387 (7)	0.0261 (6)	−0.0004 (6)	0.0078 (5)	−0.0036 (5)
C17	0.0304 (6)	0.0322 (7)	0.0305 (6)	0.0004 (5)	0.0071 (5)	−0.0021 (5)
C18	0.0426 (7)	0.0531 (8)	0.0270 (7)	−0.0044 (6)	0.0082 (6)	−0.0045 (6)
C19	0.0318 (7)	0.0548 (8)	0.0349 (7)	−0.0041 (6)	0.0089 (6)	0.0029 (6)

Geometric parameters (Å, º) top

C1—C2	1.385 (5)	C12B—H12D	1.0338
C1—C12A	1.393 (8)	C14B—C16B	1.497 (5)
C1—H1	0.9300	C14B—C15B	1.501 (8)
C2—C3	1.391 (4)	C14B—H14B	0.9800
C2—C14	1.522 (6)	C15B—H15D	0.9600
C3—C4	1.379 (7)	C15B—H15E	0.9600
C3—H3	0.9300	C15B—H15F	0.9600
C4—C4A	1.398 (8)	C16B—H16D	0.9600
C4—H4	0.9300	C16B—H16E	0.9600
C4A—N5	1.379 (12)	C16B—H16F	0.9600
C4A—C12A	1.393 (7)	N5—C13	1.4613 (16)
C12—N11	1.52 (2)	N5—C6	1.4730 (16)
C12—C12A	1.531 (8)	C6—C6A	1.5163 (16)
C12—H12A	0.9700	C6—H6A	1.0077
C12—H12B	0.9700	C6—H6B	1.0077
C14—C15	1.487 (6)	C6A—C7	1.3941 (16)
C14—C16	1.524 (5)	C6A—C10A	1.3990 (17)
C14—H14A	0.9800	C7—C8	1.3895 (16)
C15—H15A	0.9600	C7—H7	0.9781
C15—H15B	0.9600	C8—C9	1.3937 (17)
C15—H15C	0.9600	C8—C17	1.5165 (16)
C16—H16A	0.9600	C9—C10	1.3802 (17)
C16—H16B	0.9600	C9—H9	0.9941
C16—H16C	0.9600	C10—C10A	1.3914 (17)
C1B—C2B	1.389 (8)	C10—H10	0.9716
C1B—C32A	1.407 (11)	C10A—N11	1.4350 (15)
C1B—H1B	1.0345	N11—C13	1.4651 (16)
C2B—C3B	1.388 (6)	C13—H13A	1.0089
C2B—C14B	1.531 (9)	C13—H13B	1.0089
C3B—C4B	1.390 (9)	C17—C18	1.5258 (18)
C3B—H3B	1.0423	C17—C19	1.5285 (17)
C4B—C24A	1.397 (11)	C17—H17	1.0057
C4B—H4B	1.0724	C18—H18A	1.0068
C24A—C32A	1.389 (10)	C18—H18B	1.0068
C24A—N5	1.533 (16)	C18—H18C	1.0068
C12B—N11	1.42 (3)	C19—H19A	1.0103
C12B—C32A	1.481 (11)	C19—H19B	1.0103
C12B—H12C	1.0338	C19—H19C	1.0103

C2—C1—C12A	120.9 (5)	H15E—C15B—H15F	109.5
C2—C1—H1	119.6	C14B—C16B—H16D	109.5
C12A—C1—H1	119.6	C14B—C16B—H16E	109.5
C1—C2—C3	118.2 (5)	H16D—C16B—H16E	109.5
C1—C2—C14	122.5 (4)	C14B—C16B—H16F	109.5
C3—C2—C14	119.2 (4)	H16D—C16B—H16F	109.5
C4—C3—C2	122.1 (4)	H16E—C16B—H16F	109.5
C4—C3—H3	119.0	C4A—N5—C13	113.7 (4)
C2—C3—H3	119.0	C4A—N5—C6	113.3 (6)
C3—C4—C4A	119.2 (6)	C13—N5—C6	108.29 (10)
C3—C4—H4	120.4	C13—N5—C24A	106.2 (5)
C4A—C4—H4	120.4	C6—N5—C24A	110.2 (7)
N5—C4A—C12A	120.3 (7)	N5—C6—C6A	112.71 (10)
N5—C4A—C4	120.2 (7)	N5—C6—H6A	109.0
C12A—C4A—C4	119.4 (8)	C6A—C6—H6A	109.0
N11—C12—C12A	113.9 (13)	N5—C6—H6B	109.0
N11—C12—H12A	108.8	C6A—C6—H6B	109.0
C12A—C12—H12A	108.8	H6A—C6—H6B	107.8
N11—C12—H12B	108.8	C7—C6A—C10A	118.95 (11)
C12A—C12—H12B	108.8	C7—C6A—C6	120.87 (10)
H12A—C12—H12B	107.7	C10A—C6A—C6	120.17 (10)
C4A—C12A—C1	120.1 (7)	C8—C7—C6A	122.30 (11)
C4A—C12A—C12	120.5 (11)	C8—C7—H7	118.9
C1—C12A—C12	119.4 (10)	C6A—C7—H7	118.9
C15—C14—C2	110.8 (4)	C7—C8—C9	117.59 (11)
C15—C14—C16	109.6 (4)	C7—C8—C17	120.34 (11)
C2—C14—C16	113.8 (3)	C9—C8—C17	122.01 (11)
C15—C14—H14A	107.5	C10—C9—C8	121.18 (11)
C2—C14—H14A	107.5	C10—C9—H9	119.4
C16—C14—H14A	107.5	C8—C9—H9	119.4
C2B—C1B—C32A	123.5 (8)	C9—C10—C10A	120.81 (11)
C2B—C1B—H1B	118.2	C9—C10—H10	119.6
C32A—C1B—H1B	118.2	C10A—C10—H10	119.6
C3B—C2B—C1B	117.5 (7)	C10—C10A—C6A	119.17 (11)
C3B—C2B—C14B	121.6 (6)	C10—C10A—N11	118.87 (11)
C1B—C2B—C14B	120.9 (6)	C6A—C10A—N11	121.94 (11)
C2B—C3B—C4B	120.5 (7)	C12B—N11—C10A	112.8 (13)
C2B—C3B—H3B	119.7	C12B—N11—C13	112.1 (10)
C4B—C3B—H3B	119.7	C10A—N11—C13	110.38 (10)
C3B—C4B—C24A	120.8 (8)	C10A—N11—C12	111.7 (9)
C3B—C4B—H4B	119.6	C13—N11—C12	105.5 (7)
C24A—C4B—H4B	119.6	N5—C13—N11	112.08 (10)
C32A—C24A—C4B	120.1 (13)	N5—C13—H13A	109.2
C32A—C24A—N5	123.1 (11)	N11—C13—H13A	109.2
C4B—C24A—N5	116.3 (9)	N5—C13—H13B	109.2
N11—C12B—C32A	110.9 (18)	N11—C13—H13B	109.2
N11—C12B—H12C	109.5	H13A—C13—H13B	107.9
C32A—C12B—H12C	109.5	C8—C17—C18	113.27 (11)
N11—C12B—H12D	109.5	C8—C17—C19	109.81 (10)
C32A—C12B—H12D	109.5	C18—C17—C19	110.44 (10)
H12C—C12B—H12D	108.0	C8—C17—H17	107.7
C24A—C32A—C1B	117.4 (11)	C18—C17—H17	107.7
C24A—C32A—C12B	121.0 (16)	C19—C17—H17	107.7
C1B—C32A—C12B	121.6 (15)	C17—C18—H18A	109.5
C16B—C14B—C15B	111.8 (5)	C17—C18—H18B	109.5
C16B—C14B—C2B	112.9 (4)	H18A—C18—H18B	109.5
C15B—C14B—C2B	110.0 (6)	C17—C18—H18C	109.5
C16B—C14B—H14B	107.3	H18A—C18—H18C	109.5
C15B—C14B—H14B	107.3	H18B—C18—H18C	109.5
C2B—C14B—H14B	107.3	C17—C19—H19A	109.5
C14B—C15B—H15D	109.5	C17—C19—H19B	109.5
C14B—C15B—H15E	109.5	H19A—C19—H19B	109.5
H15D—C15B—H15E	109.5	C17—C19—H19C	109.5
C14B—C15B—H15F	109.5	H19A—C19—H19C	109.5
H15D—C15B—H15F	109.5	H19B—C19—H19C	109.5

C12A—C1—C2—C3	0.7 (12)	C4B—C24A—N5—C4A	24 (6)
C12A—C1—C2—C14	−175.9 (8)	C32A—C24A—N5—C13	−13.7 (18)
C1—C2—C3—C4	0.5 (10)	C4B—C24A—N5—C13	158.3 (12)
C14—C2—C3—C4	177.3 (6)	C32A—C24A—N5—C6	103.4 (16)
C2—C3—C4—C4A	−3.5 (12)	C4B—C24A—N5—C6	−84.6 (14)
C3—C4—C4A—N5	−178.4 (8)	C4A—N5—C6—C6A	−83.0 (3)
C3—C4—C4A—C12A	5.1 (16)	C13—N5—C6—C6A	44.16 (13)
N5—C4A—C12A—C1	179.6 (10)	C24A—N5—C6—C6A	−71.6 (4)
C4—C4A—C12A—C1	−3.9 (18)	N5—C6—C6A—C7	168.96 (10)
N5—C4A—C12A—C12	−0.9 (19)	N5—C6—C6A—C10A	−11.92 (16)
C4—C4A—C12A—C12	175.6 (14)	C10A—C6A—C7—C8	0.40 (17)
C2—C1—C12A—C4A	1.0 (16)	C6—C6A—C7—C8	179.53 (11)
C2—C1—C12A—C12	−178.6 (12)	C6A—C7—C8—C9	−0.12 (17)
N11—C12—C12A—C4A	−10 (2)	C6A—C7—C8—C17	−177.18 (10)
N11—C12—C12A—C1	169.5 (12)	C7—C8—C9—C10	−0.25 (17)
C1—C2—C14—C15	91.2 (7)	C17—C8—C9—C10	176.76 (11)
C3—C2—C14—C15	−85.4 (6)	C8—C9—C10—C10A	0.33 (17)
C1—C2—C14—C16	−32.8 (7)	C9—C10—C10A—C6A	−0.04 (17)
C3—C2—C14—C16	150.6 (5)	C9—C10—C10A—N11	−178.55 (11)
C32A—C1B—C2B—C3B	0.1 (17)	C7—C6A—C10A—C10	−0.31 (16)
C32A—C1B—C2B—C14B	179.7 (11)	C6—C6A—C10A—C10	−179.44 (10)
C1B—C2B—C3B—C4B	−2.7 (14)	C7—C6A—C10A—N11	178.14 (10)
C14B—C2B—C3B—C4B	177.6 (8)	C6—C6A—C10A—N11	−0.99 (17)
C2B—C3B—C4B—C24A	5.1 (17)	C32A—C12B—N11—C10A	−79 (2)
C3B—C4B—C24A—C32A	−5 (2)	C32A—C12B—N11—C13	47 (2)
C3B—C4B—C24A—N5	−176.9 (11)	C32A—C12B—N11—C12	6 (13)
C4B—C24A—C32A—C1B	2 (2)	C10—C10A—N11—C12B	−74.8 (7)
N5—C24A—C32A—C1B	173.7 (13)	C6A—C10A—N11—C12B	106.8 (7)
C4B—C24A—C32A—C12B	−177.8 (19)	C10—C10A—N11—C13	158.98 (10)
N5—C24A—C32A—C12B	−6 (3)	C6A—C10A—N11—C13	−19.48 (15)
C2B—C1B—C32A—C24A	0 (2)	C10—C10A—N11—C12	−84.0 (6)
C2B—C1B—C32A—C12B	−179.9 (17)	C6A—C10A—N11—C12	97.6 (6)
N11—C12B—C32A—C24A	−10 (3)	C12A—C12—N11—C12B	−178 (16)
N11—C12B—C32A—C1B	169.9 (16)	C12A—C12—N11—C10A	−79.0 (15)
C3B—C2B—C14B—C16B	50.4 (9)	C12A—C12—N11—C13	41.0 (16)
C1B—C2B—C14B—C16B	−129.3 (8)	C4A—N5—C13—N11	58.3 (5)
C3B—C2B—C14B—C15B	−75.3 (9)	C6—N5—C13—N11	−68.61 (13)
C1B—C2B—C14B—C15B	105.0 (9)	C24A—N5—C13—N11	49.7 (7)
C12A—C4A—N5—C13	−21.8 (13)	C12B—N11—C13—N5	−71.8 (11)
C4—C4A—N5—C13	161.7 (8)	C10A—N11—C13—N5	54.84 (13)
C12A—C4A—N5—C6	102.4 (11)	C12—N11—C13—N5	−66.0 (8)
C4—C4A—N5—C6	−74.1 (10)	C7—C8—C17—C18	−148.05 (11)
C12A—C4A—N5—C24A	27 (6)	C9—C8—C17—C18	35.03 (16)
C4—C4A—N5—C24A	−150 (8)	C7—C8—C17—C19	87.96 (14)
C32A—C24A—N5—C4A	−148 (8)	C9—C8—C17—C19	−88.96 (14)

2,8-bis(tert-butyl)-6H,12H-5,11-methanodibenzo[bf][1,5]diazocine (4a) top

Crystal data top

C₂₃H₃₀N₂	F(000) = 728
M_r = 334.49	D_x = 1.162 Mg m⁻³
Monoclinic, P2₁/c	Melting point = 480–482 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 15.529 (4) Å	Cell parameters from 8654 reflections
b = 12.186 (3) Å	θ = 2.6–26.4°
c = 10.764 (2) Å	µ = 0.07 mm⁻¹
β = 110.147 (6)°	T = 90 K
V = 1912.3 (8) Å³	Needle, colourless
Z = 4	0.25 × 0.2 × 0.15 mm

Data collection top

Area detector diffractometer Bruker APEXII	3955 independent reflections
Radiation source: Rigaku rotating anode	3197 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 26.6°, θ_min = 1.4°
Absorption correction: multi-scan SADABS 2007/4	h = −19→19
T_min = 0.858, T_max = 0.989	k = −15→15
31760 measured reflections	l = −13→13

Refinement top

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.14	w = 1/[σ²(F_o²) + (0.0213P)² + 2.0631P] where P = (F_o² + 2F_c²)/3
3955 reflections	(Δ/σ)_max < 0.001
247 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.64043 (12)	0.73445 (15)	0.72225 (17)	0.0181 (4)
H1	0.6238 (4)	0.6682 (14)	0.7629 (9)	0.022*
C2	0.59087 (12)	0.83062 (15)	0.71615 (17)	0.0182 (4)
C3	0.61812 (12)	0.92316 (15)	0.66088 (17)	0.0198 (4)
H3	0.5862 (7)	0.9942 (16)	0.65881 (18)	0.024*
C4	0.68859 (12)	0.91756 (15)	0.60905 (17)	0.0187 (4)
H4	0.7053 (4)	0.9827 (15)	0.5704 (9)	0.022*
C4A	0.73562 (12)	0.81925 (15)	0.61189 (16)	0.0174 (4)
N5	0.80456 (10)	0.81446 (13)	0.54934 (14)	0.0180 (3)
C6	0.89083 (12)	0.86750 (15)	0.62846 (17)	0.0179 (4)
H6A	0.8770 (2)	0.9381 (10)	0.6638 (5)	0.021*
H6B	0.9272 (5)	0.8841 (3)	0.5707 (8)	0.021*
C6A	0.94725 (12)	0.79617 (15)	0.74229 (16)	0.0171 (4)
C7	1.02184 (12)	0.83980 (15)	0.84231 (17)	0.0172 (4)
H7	1.0380 (4)	0.9185 (17)	0.8370 (2)	0.021*
C8	1.07476 (12)	0.77774 (15)	0.94955 (17)	0.0173 (4)
C9	1.05174 (12)	0.66695 (15)	0.95222 (17)	0.0190 (4)
H9	1.0882 (8)	0.6208 (10)	1.0250 (16)	0.023*
C10	0.97803 (12)	0.62216 (15)	0.85300 (17)	0.0189 (4)
H10	0.9636 (4)	0.5467 (18)	0.8569 (2)	0.023*
C10A	0.92489 (12)	0.68552 (15)	0.74800 (17)	0.0172 (4)
N11	0.84984 (10)	0.63498 (13)	0.64700 (14)	0.0194 (3)
C12	0.76765 (12)	0.62239 (15)	0.68640 (18)	0.0200 (4)
H12A	0.7871 (3)	0.5976 (4)	0.7788 (14)	0.024*
H12B	0.7277 (6)	0.5655 (9)	0.6312 (8)	0.024*
C12A	0.71345 (12)	0.72760 (15)	0.67284 (17)	0.0182 (4)
C13	0.82438 (13)	0.70026 (15)	0.52600 (17)	0.0206 (4)
H13A	0.7686 (8)	0.6669 (5)	0.4579 (10)	0.025*
H13B	0.8760 (7)	0.69850 (16)	0.4894 (6)	0.025*
C14	0.50886 (12)	0.83902 (15)	0.76575 (17)	0.0192 (4)
C15	0.48379 (14)	0.72822 (16)	0.8113 (2)	0.0270 (4)
H15A	0.5384 (8)	0.6997 (7)	0.8902 (13)	0.040*
H15B	0.4688 (9)	0.6727 (8)	0.7343 (11)	0.040*
H15C	0.4273 (9)	0.7377 (3)	0.8400 (14)	0.040*
C16	0.42548 (13)	0.88286 (18)	0.6539 (2)	0.0277 (4)
H16A	0.3724 (8)	0.8879 (12)	0.6850 (6)	0.042*
H16B	0.4103 (7)	0.8324 (9)	0.5770 (12)	0.042*
H16C	0.4396 (4)	0.9567 (11)	0.6272 (11)	0.042*
C17	0.53105 (14)	0.91878 (17)	0.88217 (19)	0.0258 (4)
H17A	0.5475 (10)	0.9904 (10)	0.8554 (6)	0.039*
H17B	0.5827 (9)	0.8903 (7)	0.9564 (11)	0.039*
H17C	0.4773 (8)	0.9268 (9)	0.9093 (10)	0.039*
C18	1.15463 (12)	0.83101 (16)	1.05807 (17)	0.0196 (4)
C19	1.19453 (13)	0.75528 (18)	1.17653 (19)	0.0283 (5)
H19A	1.1456 (7)	0.7359 (10)	1.2140 (10)	0.043*
H19B	1.2463 (10)	0.7934 (7)	1.2459 (11)	0.043*
H19C	1.2180 (10)	0.6866 (11)	1.1478 (5)	0.043*
C20	1.12056 (13)	0.93568 (18)	1.10663 (19)	0.0280 (4)
H20A	1.0713 (10)	0.9154 (3)	1.1459 (14)	0.042*
H20B	1.0933 (10)	0.9882 (9)	1.0287 (10)	0.042*
H20C	1.1743 (7)	0.9730 (8)	1.1775 (14)	0.042*
C21	1.23082 (12)	0.86165 (17)	1.00215 (18)	0.0229 (4)
H21A	1.2823 (8)	0.9001 (11)	1.0727 (10)	0.034*
H21B	1.2048 (4)	0.9120 (11)	0.9237 (13)	0.034*
H21C	1.2550 (7)	0.7929 (9)	0.9736 (13)	0.034*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0184 (8)	0.0174 (9)	0.0174 (8)	−0.0023 (7)	0.0048 (7)	−0.0009 (7)
C2	0.0171 (8)	0.0204 (9)	0.0157 (8)	0.0001 (7)	0.0038 (7)	−0.0024 (7)
C3	0.0194 (9)	0.0191 (9)	0.0196 (9)	0.0010 (7)	0.0051 (7)	−0.0009 (7)
C4	0.0181 (9)	0.0181 (9)	0.0182 (8)	−0.0002 (7)	0.0041 (7)	0.0016 (7)
C4A	0.0150 (8)	0.0214 (9)	0.0142 (8)	0.0000 (7)	0.0031 (7)	−0.0021 (7)
N5	0.0170 (7)	0.0216 (8)	0.0159 (7)	0.0004 (6)	0.0062 (6)	−0.0019 (6)
C6	0.0181 (8)	0.0205 (9)	0.0161 (8)	0.0005 (7)	0.0072 (7)	0.0012 (7)
C6A	0.0171 (8)	0.0210 (9)	0.0162 (8)	0.0021 (7)	0.0097 (7)	0.0003 (7)
C7	0.0178 (8)	0.0191 (9)	0.0177 (8)	0.0001 (7)	0.0098 (7)	0.0003 (7)
C8	0.0154 (8)	0.0224 (9)	0.0170 (8)	0.0013 (7)	0.0090 (7)	0.0005 (7)
C9	0.0205 (9)	0.0204 (9)	0.0185 (8)	0.0045 (7)	0.0098 (7)	0.0036 (7)
C10	0.0206 (9)	0.0173 (9)	0.0221 (9)	0.0016 (7)	0.0115 (7)	0.0006 (7)
C10A	0.0171 (8)	0.0195 (9)	0.0175 (8)	0.0009 (7)	0.0092 (7)	−0.0024 (7)
N11	0.0194 (7)	0.0209 (8)	0.0183 (7)	0.0001 (6)	0.0071 (6)	−0.0029 (6)
C12	0.0170 (8)	0.0187 (9)	0.0245 (9)	−0.0014 (7)	0.0076 (7)	−0.0023 (7)
C12A	0.0195 (9)	0.0182 (9)	0.0157 (8)	−0.0017 (7)	0.0044 (7)	−0.0029 (7)
C13	0.0223 (9)	0.0226 (9)	0.0169 (8)	0.0019 (7)	0.0068 (7)	−0.0037 (7)
C14	0.0185 (9)	0.0197 (9)	0.0203 (9)	0.0011 (7)	0.0078 (7)	−0.0004 (7)
C15	0.0264 (10)	0.0231 (10)	0.0368 (11)	−0.0016 (8)	0.0177 (9)	0.0013 (8)
C16	0.0170 (9)	0.0385 (12)	0.0273 (10)	0.0013 (8)	0.0071 (8)	0.0048 (9)
C17	0.0290 (10)	0.0263 (10)	0.0247 (9)	0.0014 (8)	0.0125 (8)	−0.0045 (8)
C18	0.0169 (8)	0.0260 (10)	0.0166 (8)	0.0001 (7)	0.0066 (7)	0.0014 (7)
C19	0.0218 (9)	0.0399 (12)	0.0209 (9)	−0.0027 (9)	0.0042 (8)	0.0078 (8)
C20	0.0223 (10)	0.0365 (12)	0.0239 (10)	0.0001 (9)	0.0062 (8)	−0.0097 (8)
C21	0.0183 (9)	0.0309 (11)	0.0202 (9)	−0.0032 (8)	0.0075 (7)	−0.0002 (8)

Geometric parameters (Å, º) top

C1—C2	1.391 (2)	C12—C12A	1.513 (2)
C1—C12A	1.411 (2)	C12—H12A	0.9826
C1—H1	0.9939	C12—H12B	0.9826
C2—C3	1.406 (3)	C13—H13A	1.0081
C2—C14	1.545 (2)	C13—H13B	1.0081
C3—C4	1.391 (3)	C14—C17	1.529 (3)
C3—H3	0.9941	C14—C16	1.529 (3)
C4—C4A	1.398 (3)	C14—C15	1.532 (3)
C4—H4	0.9727	C15—H15A	1.0320
C4A—C12A	1.397 (2)	C15—H15B	1.0320
C4A—N5	1.449 (2)	C15—H15C	1.0320
N5—C13	1.465 (2)	C16—H16A	0.9924
N5—C6	1.467 (2)	C16—H16B	0.9924
C6—C6A	1.512 (2)	C16—H16C	0.9924
C6—H6A	0.9934	C17—H17A	0.9802
C6—H6B	0.9934	C17—H17B	0.9802
C6A—C7	1.387 (2)	C17—H17C	0.9802
C6A—C10A	1.399 (3)	C18—C19	1.522 (3)
C7—C8	1.388 (2)	C18—C20	1.540 (3)
C7—H7	0.9975	C18—C21	1.547 (2)
C8—C9	1.399 (3)	C19—H19A	1.0033
C8—C18	1.525 (2)	C19—H19B	1.0033
C9—C10	1.381 (3)	C19—H19C	1.0033
C9—H9	0.9721	C20—H20A	1.0234
C10—C10A	1.383 (2)	C20—H20B	1.0234
C10—H10	0.9512	C20—H20C	1.0234
C10A—N11	1.431 (2)	C21—H21A	1.0085
N11—C13	1.460 (2)	C21—H21B	1.0085
N11—C12	1.485 (2)	C21—H21C	1.0085

C2—C1—C12A	122.37 (17)	N11—C13—N5	111.90 (14)
C2—C1—H1	118.8	N11—C13—H13A	109.2
C12A—C1—H1	118.8	N5—C13—H13A	109.2
C1—C2—C3	116.96 (16)	N11—C13—H13B	109.2
C1—C2—C14	123.24 (16)	N5—C13—H13B	109.2
C3—C2—C14	119.80 (16)	H13A—C13—H13B	107.9
C4—C3—C2	121.55 (17)	C17—C14—C16	108.29 (16)
C4—C3—H3	119.2	C17—C14—C15	107.98 (15)
C2—C3—H3	119.2	C16—C14—C15	108.67 (16)
C3—C4—C4A	120.71 (17)	C17—C14—C2	110.22 (15)
C3—C4—H4	119.6	C16—C14—C2	109.07 (15)
C4A—C4—H4	119.6	C15—C14—C2	112.51 (15)
C12A—C4A—C4	118.94 (16)	C14—C15—H15A	109.5
C12A—C4A—N5	121.80 (16)	C14—C15—H15B	109.5
C4—C4A—N5	119.24 (16)	H15A—C15—H15B	109.5
C4A—N5—C13	110.51 (14)	C14—C15—H15C	109.5
C4A—N5—C6	112.69 (13)	H15A—C15—H15C	109.5
C13—N5—C6	108.31 (14)	H15B—C15—H15C	109.5
N5—C6—C6A	112.07 (15)	C14—C16—H16A	109.5
N5—C6—H6A	109.2	C14—C16—H16B	109.5
C6A—C6—H6A	109.2	H16A—C16—H16B	109.5
N5—C6—H6B	109.2	C14—C16—H16C	109.5
C6A—C6—H6B	109.2	H16A—C16—H16C	109.5
H6A—C6—H6B	107.9	H16B—C16—H16C	109.5
C7—C6A—C10A	119.26 (16)	C14—C17—H17A	109.5
C7—C6A—C6	120.31 (16)	C14—C17—H17B	109.5
C10A—C6A—C6	120.43 (16)	H17A—C17—H17B	109.5
C6A—C7—C8	122.25 (17)	C14—C17—H17C	109.5
C6A—C7—H7	118.9	H17A—C17—H17C	109.5
C8—C7—H7	118.9	H17B—C17—H17C	109.5
C7—C8—C9	117.42 (17)	C19—C18—C8	111.87 (16)
C7—C8—C18	119.83 (16)	C19—C18—C20	107.83 (16)
C9—C8—C18	122.75 (16)	C8—C18—C20	109.18 (15)
C10—C9—C8	121.00 (17)	C19—C18—C21	109.10 (15)
C10—C9—H9	119.5	C8—C18—C21	109.51 (14)
C8—C9—H9	119.5	C20—C18—C21	109.30 (16)
C9—C10—C10A	120.92 (17)	C18—C19—H19A	109.5
C9—C10—H10	119.5	C18—C19—H19B	109.5
C10A—C10—H10	119.5	H19A—C19—H19B	109.5
C10—C10A—C6A	119.13 (16)	C18—C19—H19C	109.5
C10—C10A—N11	118.77 (16)	H19A—C19—H19C	109.5
C6A—C10A—N11	122.08 (16)	H19B—C19—H19C	109.5
C10A—N11—C13	110.05 (15)	C18—C20—H20A	109.5
C10A—N11—C12	112.50 (14)	C18—C20—H20B	109.5
C13—N11—C12	108.40 (14)	H20A—C20—H20B	109.5
N11—C12—C12A	112.91 (15)	C18—C20—H20C	109.5
N11—C12—H12A	109.0	H20A—C20—H20C	109.5
C12A—C12—H12A	109.0	H20B—C20—H20C	109.5
N11—C12—H12B	109.0	C18—C21—H21A	109.5
C12A—C12—H12B	109.0	C18—C21—H21B	109.5
H12A—C12—H12B	107.8	H21A—C21—H21B	109.5
C4A—C12A—C1	119.32 (17)	C18—C21—H21C	109.5
C4A—C12A—C12	120.26 (16)	H21A—C21—H21C	109.5
C1—C12A—C12	120.42 (16)	H21B—C21—H21C	109.5

C12A—C1—C2—C3	−1.5 (3)	C6A—C10A—N11—C13	19.2 (2)
C12A—C1—C2—C14	178.09 (16)	C10—C10A—N11—C12	79.6 (2)
C1—C2—C3—C4	2.9 (3)	C6A—C10A—N11—C12	−101.76 (19)
C14—C2—C3—C4	−176.72 (16)	C10A—N11—C12—C12A	79.16 (19)
C2—C3—C4—C4A	−0.8 (3)	C13—N11—C12—C12A	−42.77 (19)
C3—C4—C4A—C12A	−2.7 (3)	C4—C4A—C12A—C1	4.1 (2)
C3—C4—C4A—N5	175.99 (15)	N5—C4A—C12A—C1	−174.65 (15)
C12A—C4A—N5—C13	16.6 (2)	C4—C4A—C12A—C12	−175.56 (15)
C4—C4A—N5—C13	−162.14 (15)	N5—C4A—C12A—C12	5.7 (2)
C12A—C4A—N5—C6	−104.77 (19)	C2—C1—C12A—C4A	−1.9 (3)
C4—C4A—N5—C6	76.53 (19)	C2—C1—C12A—C12	177.67 (16)
C4A—N5—C6—C6A	77.60 (18)	N11—C12—C12A—C4A	8.0 (2)
C13—N5—C6—C6A	−44.97 (18)	N11—C12—C12A—C1	−171.57 (15)
N5—C6—C6A—C7	−167.56 (15)	C10A—N11—C13—N5	−54.77 (19)
N5—C6—C6A—C10A	12.4 (2)	C12—N11—C13—N5	68.65 (18)
C10A—C6A—C7—C8	−0.9 (2)	C4A—N5—C13—N11	−54.32 (19)
C6—C6A—C7—C8	179.10 (15)	C6—N5—C13—N11	69.56 (17)
C6A—C7—C8—C9	1.7 (2)	C1—C2—C14—C17	115.89 (19)
C6A—C7—C8—C18	−178.60 (15)	C3—C2—C14—C17	−64.5 (2)
C7—C8—C9—C10	−1.2 (2)	C1—C2—C14—C16	−125.34 (18)
C18—C8—C9—C10	179.03 (16)	C3—C2—C14—C16	54.3 (2)
C8—C9—C10—C10A	0.1 (3)	C1—C2—C14—C15	−4.7 (2)
C9—C10—C10A—C6A	0.7 (2)	C3—C2—C14—C15	174.93 (16)
C9—C10—C10A—N11	179.36 (15)	C7—C8—C18—C19	171.06 (16)
C7—C6A—C10A—C10	−0.3 (2)	C9—C8—C18—C19	−9.2 (2)
C6—C6A—C10A—C10	179.68 (15)	C7—C8—C18—C20	51.8 (2)
C7—C6A—C10A—N11	−178.91 (15)	C9—C8—C18—C20	−128.49 (18)
C6—C6A—C10A—N11	1.1 (2)	C7—C8—C18—C21	−67.9 (2)
C10—C10A—N11—C13	−159.36 (15)	C9—C8—C18—C21	111.87 (18)

S,S-2,8-bis(tert-butyl)-6H,12H-5,11-methanodibenzo[bf][1,5]diazocine (4b) top

Crystal data top

C₂₃H₃₀N₂	D_x = 1.127 Mg m⁻³
M_r = 334.49	Melting point = 449–450 K
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
a = 28.370 (2) Å	Cell parameters from 2307 reflections
b = 6.6841 (5) Å	θ = 2.8–22.6°
c = 21.6271 (16) Å	µ = 0.07 mm⁻¹
β = 105.940 (1)°	T = 100 K
V = 3943.4 (5) Å³	Rod, colourless
Z = 8	0.45 × 0.25 × 0.21 mm
F(000) = 1456

Data collection top

Area detector diffractometer Bruker APEXII	6393 independent reflections
Radiation source: fine-focus sealed tube	4971 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
ω scans	θ_max = 30.7°, θ_min = 1.5°
Absorption correction: multi-scan Bruker SADABS 2008/1	h = −37→40
T_min = 0.648, T_max = 0.746	k = −9→9
17606 measured reflections	l = −30→21

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.120	Riding
S = 1.01	w = 1/[σ²(F_o²) + (0.0437P)² + 1.884P] where P = (F_o² + 2F_c²)/3
6393 reflections	(Δ/σ)_max < 0.001
488 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.25 e Å⁻³

Special details top

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.29705 (9)	0.6997 (4)	0.31657 (12)	0.0253 (5)
H1	0.2740 (7)	0.808 (3)	0.3000 (5)	0.030*
C2	0.28092 (9)	0.5360 (4)	0.34443 (12)	0.0272 (6)
C3	0.31513 (9)	0.3820 (4)	0.36717 (12)	0.0273 (6)
H3	0.3045 (3)	0.258 (4)	0.3861 (6)	0.033*
C4	0.36311 (9)	0.3976 (4)	0.36395 (12)	0.0240 (5)
H4	0.3867 (7)	0.288 (3)	0.3812 (5)	0.029*
C4A	0.37873 (8)	0.5650 (4)	0.33690 (11)	0.0210 (5)
N5	0.42947 (7)	0.5831 (3)	0.33819 (10)	0.0222 (4)
C6	0.44329 (9)	0.4557 (4)	0.29018 (11)	0.0228 (5)
H6A	0.4287 (3)	0.322 (3)	0.29024 (11)	0.027*
H6B	0.4791 (7)	0.4398 (5)	0.3023 (3)	0.027*
C6A	0.42644 (8)	0.5431 (4)	0.22294 (11)	0.0190 (5)
C7	0.42931 (8)	0.4301 (4)	0.16940 (11)	0.0200 (5)
H7	0.4438 (4)	0.297 (4)	0.1763 (2)	0.024*
C8	0.41220 (8)	0.5014 (4)	0.10699 (12)	0.0203 (5)
C9	0.38991 (8)	0.6919 (4)	0.09871 (12)	0.0239 (5)
H9	0.3758 (4)	0.7424 (16)	0.0560 (13)	0.029*
C10	0.38810 (8)	0.8067 (4)	0.15105 (12)	0.0236 (5)
H10	0.3726 (5)	0.943 (4)	0.1439 (2)	0.028*
C10A	0.40735 (8)	0.7371 (4)	0.21368 (12)	0.0205 (5)
N11	0.40805 (7)	0.8683 (3)	0.26647 (10)	0.0228 (4)
C12	0.35941 (8)	0.8939 (4)	0.27751 (12)	0.0236 (5)
H12A	0.3340 (5)	0.9142 (6)	0.2346 (8)	0.028*
H12B	0.35969 (8)	1.019 (2)	0.3045 (5)	0.028*
C12A	0.34490 (8)	0.7163 (4)	0.31124 (11)	0.0211 (5)
C13	0.44134 (9)	0.7901 (4)	0.32588 (12)	0.0257 (5)
H13A	0.4773 (7)	0.7966 (4)	0.32245 (13)	0.031*
H13B	0.43910 (9)	0.8799 (17)	0.3645 (7)	0.031*
C14	0.22880 (9)	0.5223 (5)	0.35257 (13)	0.0323 (6)
C15	0.19571 (10)	0.6899 (5)	0.31706 (16)	0.0418 (8)
H15A	0.2094 (5)	0.825 (3)	0.3359 (8)	0.063*
H15B	0.1613 (7)	0.6717 (19)	0.3221 (9)	0.063*
H15C	0.1944 (6)	0.685 (2)	0.2694 (9)	0.063*
C16	0.23221 (11)	0.5373 (7)	0.42460 (14)	0.0531 (10)
H16A	0.2486 (10)	0.666 (3)	0.4421 (5)	0.080*
H16B	0.2517 (10)	0.422 (3)	0.4479 (5)	0.080*
H16C	0.1985 (7)	0.534 (4)	0.4306 (2)	0.080*
C17	0.20557 (11)	0.3216 (6)	0.32623 (16)	0.0434 (8)
H17A	0.1699 (7)	0.3137 (14)	0.3314 (10)	0.065*
H17B	0.2267 (6)	0.204 (2)	0.3519 (8)	0.065*
H17C	0.2042 (7)	0.3098 (15)	0.2774 (9)	0.065*
C18	0.41706 (8)	0.3845 (4)	0.04798 (11)	0.0226 (5)
C19	0.45361 (10)	0.2114 (5)	0.06723 (13)	0.0343 (7)
H19A	0.4866 (6)	0.2654 (11)	0.0929 (9)	0.051*
H19B	0.4574 (6)	0.142 (2)	0.0271 (7)	0.051*
H19C	0.4411 (4)	0.112 (2)	0.0944 (9)	0.051*
C20	0.36696 (9)	0.2989 (5)	0.01183 (13)	0.0320 (6)
H20A	0.3550 (4)	0.207 (3)	0.0411 (6)	0.048*
H20B	0.37011 (17)	0.222 (3)	−0.0267 (8)	0.048*
H20C	0.3430 (4)	0.4112 (19)	−0.0025 (8)	0.048*
C21	0.43538 (10)	0.5236 (5)	0.00310 (13)	0.0329 (6)
H21A	0.4108 (5)	0.631 (2)	−0.0130 (8)	0.049*
H21B	0.4401 (7)	0.4453 (15)	−0.0339 (8)	0.049*
H21C	0.4671 (6)	0.585 (3)	0.0271 (5)	0.049*
C31	0.07716 (8)	0.1661 (4)	0.33962 (12)	0.0231 (5)
H31	0.0834 (2)	0.028 (5)	0.3519 (4)	0.028*
C32	0.08023 (9)	0.3079 (4)	0.38772 (12)	0.0270 (6)
C33	0.07059 (9)	0.5062 (4)	0.36824 (12)	0.0261 (6)
H33	0.07246 (11)	0.607 (3)	0.3997 (10)	0.031*
C34	0.05832 (8)	0.5588 (4)	0.30370 (12)	0.0209 (5)
H34	0.0513 (2)	0.701 (4)	0.2911 (4)	0.025*
C34A	0.05572 (7)	0.4150 (3)	0.25625 (11)	0.0169 (4)
N35	0.04248 (6)	0.4747 (3)	0.18992 (9)	0.0176 (4)
C36	0.08316 (8)	0.5691 (4)	0.17003 (12)	0.0189 (5)
H36A	0.1013 (3)	0.6646 (18)	0.2052 (6)	0.023*
H36B	0.0690 (3)	0.6509 (15)	0.1295 (7)	0.023*
C36A	0.11926 (8)	0.4191 (3)	0.15718 (11)	0.0167 (4)
C37	0.16340 (8)	0.4823 (3)	0.14638 (11)	0.0170 (4)
H37	0.16942 (19)	0.625 (4)	0.14458 (12)	0.020*
C38	0.19885 (8)	0.3504 (3)	0.13817 (11)	0.0179 (5)
C39	0.18921 (9)	0.1455 (4)	0.14262 (12)	0.0229 (5)
H39	0.2130 (7)	0.051 (3)	0.13929 (16)	0.027*
C40	0.14550 (9)	0.0801 (4)	0.15178 (12)	0.0226 (5)
H40	0.1399 (2)	−0.058 (5)	0.15416 (14)	0.027*
C40A	0.10956 (8)	0.2149 (3)	0.15757 (11)	0.0188 (5)
N41	0.06304 (7)	0.1409 (3)	0.16151 (10)	0.0201 (4)
C42	0.06483 (9)	0.0559 (4)	0.22496 (12)	0.0224 (5)
H42A	0.0943 (6)	−0.0275 (16)	0.2396 (3)	0.027*
H42B	0.0361 (5)	−0.0306 (17)	0.22088 (14)	0.027*
C42A	0.06551 (8)	0.2153 (4)	0.27465 (11)	0.0184 (5)
C43	0.02632 (8)	0.3016 (4)	0.14839 (12)	0.0220 (5)
H43A	0.01973 (15)	0.3436 (8)	0.1028 (8)	0.026*
H43B	−0.0048 (6)	0.2500 (10)	0.15492 (15)	0.026*
C44	0.09348 (10)	0.2421 (5)	0.45839 (13)	0.0386 (7)
C45	0.05465 (12)	0.0981 (7)	0.46869 (15)	0.0541 (11)
H45A	0.0222 (7)	0.1644 (19)	0.4562 (12)	0.081*
H45B	0.0628 (5)	0.059 (3)	0.5146 (10)	0.081*
H45C	0.0538 (6)	−0.023 (3)	0.4419 (11)	0.081*
C46	0.1001 (2)	0.4174 (8)	0.50413 (18)	0.0943 (19)
H46A	0.0650 (9)	0.491 (4)	0.4987 (12)	0.141*
H46B	0.1260 (12)	0.523 (4)	0.4933 (11)	0.141*
H46C	0.1142 (13)	0.3642 (17)	0.5534 (12)	0.141*
C47	0.14264 (12)	0.1262 (8)	0.47481 (18)	0.0754 (16)
H47A	0.1527 (6)	0.087 (4)	0.5239 (12)	0.113*
H47B	0.1701 (7)	0.218 (3)	0.4652 (14)	0.113*
H47C	0.1386 (3)	−0.005 (4)	0.4465 (13)	0.113*
C48	0.24560 (8)	0.4172 (4)	0.12220 (12)	0.0204 (5)
C49	0.29098 (9)	0.3200 (4)	0.16844 (14)	0.0305 (6)
H49A	0.3207 (5)	0.362 (2)	0.1567 (6)	0.046*
H49B	0.2879 (3)	0.173 (2)	0.1654 (7)	0.046*
H49C	0.2934 (4)	0.362 (2)	0.2129 (8)	0.046*
C50	0.25236 (9)	0.6444 (4)	0.12621 (14)	0.0250 (5)
H50A	0.2246 (5)	0.7094 (11)	0.0948 (7)	0.037*
H50B	0.2833 (6)	0.6802 (7)	0.1163 (8)	0.037*
H50C	0.2536 (6)	0.6903 (9)	0.1701 (7)	0.037*
C51	0.24233 (9)	0.3507 (4)	0.05278 (13)	0.0293 (6)
H51A	0.2113 (6)	0.414 (2)	0.0213 (5)	0.044*
H51B	0.2399 (7)	0.195 (3)	0.0498 (2)	0.044*
H51C	0.2735 (6)	0.398 (2)	0.0404 (4)	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0236 (11)	0.0328 (14)	0.0196 (13)	−0.0028 (10)	0.0059 (9)	−0.0055 (11)
C2	0.0250 (12)	0.0390 (15)	0.0173 (12)	−0.0101 (11)	0.0052 (9)	−0.0073 (11)
C3	0.0351 (14)	0.0304 (14)	0.0178 (12)	−0.0108 (11)	0.0097 (10)	−0.0047 (11)
C4	0.0292 (12)	0.0268 (12)	0.0156 (12)	−0.0012 (10)	0.0055 (9)	−0.0034 (10)
C4A	0.0223 (11)	0.0277 (12)	0.0127 (11)	−0.0046 (10)	0.0044 (9)	−0.0070 (10)
N5	0.0187 (9)	0.0276 (11)	0.0208 (11)	−0.0025 (8)	0.0064 (8)	−0.0036 (9)
C6	0.0223 (11)	0.0280 (13)	0.0192 (13)	0.0035 (9)	0.0073 (9)	−0.0005 (10)
C6A	0.0154 (10)	0.0232 (11)	0.0185 (12)	−0.0020 (9)	0.0049 (8)	0.0001 (10)
C7	0.0163 (10)	0.0236 (12)	0.0202 (12)	−0.0005 (9)	0.0049 (9)	−0.0007 (10)
C8	0.0151 (10)	0.0255 (12)	0.0202 (12)	−0.0030 (9)	0.0048 (9)	−0.0014 (10)
C9	0.0199 (11)	0.0302 (13)	0.0207 (13)	0.0018 (10)	0.0042 (9)	0.0043 (11)
C10	0.0206 (11)	0.0249 (12)	0.0260 (13)	0.0019 (10)	0.0079 (9)	0.0042 (11)
C10A	0.0163 (10)	0.0243 (12)	0.0212 (12)	−0.0026 (9)	0.0056 (9)	−0.0013 (10)
N11	0.0227 (10)	0.0233 (10)	0.0230 (11)	−0.0029 (8)	0.0075 (8)	−0.0047 (9)
C12	0.0223 (11)	0.0232 (12)	0.0270 (13)	−0.0019 (9)	0.0097 (10)	−0.0044 (11)
C12A	0.0239 (11)	0.0245 (12)	0.0151 (11)	−0.0034 (9)	0.0056 (9)	−0.0066 (10)
C13	0.0240 (12)	0.0316 (13)	0.0212 (13)	−0.0076 (10)	0.0059 (10)	−0.0065 (11)
C14	0.0239 (12)	0.0503 (18)	0.0243 (14)	−0.0123 (12)	0.0093 (10)	−0.0057 (13)
C15	0.0220 (13)	0.059 (2)	0.046 (2)	−0.0067 (13)	0.0123 (12)	−0.0087 (17)
C16	0.0322 (15)	0.101 (3)	0.0309 (17)	−0.0166 (19)	0.0161 (13)	−0.013 (2)
C17	0.0315 (15)	0.057 (2)	0.0402 (18)	−0.0213 (15)	0.0070 (12)	0.0020 (16)
C18	0.0184 (11)	0.0321 (13)	0.0167 (12)	−0.0006 (9)	0.0036 (9)	−0.0036 (10)
C19	0.0336 (14)	0.0430 (16)	0.0259 (15)	0.0143 (13)	0.0074 (11)	−0.0057 (13)
C20	0.0232 (12)	0.0444 (16)	0.0284 (15)	−0.0050 (12)	0.0072 (10)	−0.0106 (13)
C21	0.0333 (13)	0.0443 (17)	0.0256 (14)	−0.0054 (12)	0.0159 (11)	−0.0047 (13)
C31	0.0193 (11)	0.0254 (13)	0.0235 (13)	−0.0014 (9)	0.0041 (9)	0.0072 (11)
C32	0.0221 (11)	0.0394 (15)	0.0186 (13)	−0.0045 (11)	0.0042 (9)	0.0065 (12)
C33	0.0286 (12)	0.0302 (14)	0.0209 (13)	−0.0066 (11)	0.0095 (10)	−0.0046 (11)
C34	0.0222 (11)	0.0189 (11)	0.0230 (13)	−0.0016 (9)	0.0084 (9)	0.0015 (10)
C34A	0.0150 (10)	0.0186 (10)	0.0172 (12)	0.0003 (8)	0.0048 (8)	0.0029 (9)
N35	0.0170 (9)	0.0193 (9)	0.0169 (10)	0.0015 (7)	0.0053 (7)	0.0032 (8)
C36	0.0176 (10)	0.0178 (10)	0.0233 (12)	0.0014 (9)	0.0092 (9)	0.0039 (10)
C36A	0.0184 (10)	0.0166 (10)	0.0144 (11)	0.0004 (8)	0.0033 (8)	−0.0002 (9)
C37	0.0187 (10)	0.0146 (10)	0.0177 (12)	0.0005 (8)	0.0050 (9)	0.0010 (9)
C38	0.0197 (10)	0.0181 (11)	0.0165 (11)	0.0012 (8)	0.0061 (9)	−0.0011 (9)
C39	0.0267 (12)	0.0161 (11)	0.0288 (14)	0.0015 (9)	0.0125 (10)	−0.0024 (10)
C40	0.0295 (12)	0.0127 (11)	0.0290 (14)	0.0000 (9)	0.0137 (10)	0.0003 (10)
C40A	0.0227 (11)	0.0186 (11)	0.0160 (12)	−0.0012 (9)	0.0064 (9)	−0.0020 (9)
N41	0.0216 (9)	0.0196 (9)	0.0205 (11)	−0.0039 (8)	0.0082 (8)	−0.0036 (8)
C42	0.0239 (11)	0.0201 (11)	0.0247 (13)	−0.0026 (9)	0.0090 (9)	0.0003 (10)
C42A	0.0152 (10)	0.0214 (11)	0.0190 (12)	−0.0001 (9)	0.0055 (8)	0.0040 (10)
C43	0.0179 (10)	0.0259 (12)	0.0209 (12)	−0.0023 (9)	0.0032 (9)	0.0003 (10)
C44	0.0359 (15)	0.057 (2)	0.0202 (14)	−0.0097 (14)	0.0039 (11)	0.0076 (14)
C45	0.0394 (17)	0.093 (3)	0.0308 (18)	−0.0132 (18)	0.0110 (14)	0.0214 (19)
C46	0.166 (5)	0.087 (3)	0.0216 (19)	−0.029 (4)	0.012 (2)	−0.004 (2)
C47	0.0358 (18)	0.137 (4)	0.048 (2)	0.010 (2)	0.0027 (15)	0.048 (3)
C48	0.0193 (10)	0.0193 (11)	0.0245 (13)	0.0018 (9)	0.0093 (9)	0.0013 (10)
C49	0.0226 (12)	0.0302 (14)	0.0385 (16)	0.0047 (11)	0.0079 (11)	0.0049 (13)
C50	0.0187 (11)	0.0224 (12)	0.0350 (15)	−0.0011 (9)	0.0094 (10)	0.0006 (11)
C51	0.0292 (13)	0.0324 (15)	0.0305 (15)	−0.0012 (11)	0.0152 (11)	−0.0056 (12)

Geometric parameters (Å, º) top

C1—C2	1.386 (4)	C31—C42A	1.392 (3)
C1—C12A	1.398 (3)	C31—C32	1.392 (4)
C1—H1	0.9759	C31—H31	0.9641
C2—C3	1.408 (4)	C32—C33	1.395 (4)
C2—C14	1.539 (3)	C32—C44	1.535 (4)
C3—C4	1.386 (3)	C33—C34	1.388 (3)
C3—H3	1.0062	C33—H33	0.9493
C4—C4A	1.391 (4)	C34—C34A	1.393 (3)
C4—H4	0.9943	C34—H34	0.9955
C4A—C12A	1.400 (3)	C34A—C42A	1.399 (3)
C4A—N5	1.437 (3)	C34A—N35	1.436 (3)
N5—C13	1.466 (3)	N35—C43	1.459 (3)
N5—C6	1.476 (3)	N35—C36	1.479 (3)
C6—C6A	1.517 (3)	C36—C36A	1.513 (3)
C6—H6A	0.9833	C36—H36A	1.0169
C6—H6B	0.9833	C36—H36B	1.0169
C6A—C10A	1.398 (3)	C36A—C40A	1.393 (3)
C6A—C7	1.403 (3)	C36A—C37	1.401 (3)
C7—C8	1.388 (3)	C37—C38	1.385 (3)
C7—H7	0.9768	C37—H37	0.9714
C8—C9	1.411 (3)	C38—C39	1.405 (3)
C8—C18	1.535 (3)	C38—C48	1.526 (3)
C9—C10	1.380 (4)	C39—C40	1.380 (3)
C9—H9	0.9609	C39—H39	0.9395
C10—C10A	1.394 (3)	C40—C40A	1.392 (3)
C10—H10	1.0065	C40—H40	0.9390
C10A—N11	1.436 (3)	C40A—N41	1.434 (3)
N11—C13	1.466 (3)	N41—C43	1.469 (3)
N11—C12	1.474 (3)	N41—C42	1.473 (3)
C12—C12A	1.508 (3)	C42—C42A	1.510 (3)
C12—H12A	1.0153	C42—H42A	0.9830
C12—H12B	1.0153	C42—H42B	0.9830
C13—H13A	1.0450	C43—H43A	0.9922
C13—H13B	1.0450	C43—H43B	0.9922
C14—C15	1.527 (5)	C44—C46	1.511 (6)
C14—C17	1.533 (4)	C44—C45	1.524 (4)
C14—C16	1.537 (4)	C44—C47	1.549 (5)
C15—H15A	1.0204	C45—H45A	0.9906
C15—H15B	1.0204	C45—H45B	0.9906
C15—H15C	1.0204	C45—H45C	0.9906
C16—H16A	0.9995	C46—H46A	1.0894
C16—H16B	0.9995	C46—H46B	1.0894
C16—H16C	0.9995	C46—H46C	1.0894
C17—H17A	1.0498	C47—H47A	1.0553
C17—H17B	1.0498	C47—H47B	1.0553
C17—H17C	1.0498	C47—H47C	1.0553
C18—C20	1.533 (3)	C48—C50	1.530 (3)
C18—C19	1.533 (4)	C48—C49	1.540 (3)
C18—C21	1.534 (4)	C48—C51	1.544 (4)
C19—H19A	1.0141	C49—H49A	0.9867
C19—H19B	1.0141	C49—H49B	0.9867
C19—H19C	1.0141	C49—H49C	0.9867
C20—H20A	1.0032	C50—H50A	0.9891
C20—H20B	1.0032	C50—H50B	0.9891
C20—H20C	1.0032	C50—H50C	0.9891
C21—H21A	0.9955	C51—H51A	1.0425
C21—H21B	0.9955	C51—H51B	1.0425
C21—H21C	0.9955	C51—H51C	1.0425

C2—C1—C12A	122.8 (3)	C42A—C31—C32	122.8 (2)
C2—C1—H1	118.6	C42A—C31—H31	118.6
C12A—C1—H1	118.6	C32—C31—H31	118.6
C1—C2—C3	116.8 (2)	C31—C32—C33	117.0 (2)
C1—C2—C14	122.6 (3)	C31—C32—C44	119.8 (3)
C3—C2—C14	120.5 (2)	C33—C32—C44	123.2 (3)
C4—C3—C2	121.3 (2)	C34—C33—C32	121.2 (2)
C4—C3—H3	119.3	C34—C33—H33	119.4
C2—C3—H3	119.3	C32—C33—H33	119.4
C3—C4—C4A	120.8 (2)	C33—C34—C34A	120.9 (2)
C3—C4—H4	119.6	C33—C34—H34	119.5
C4A—C4—H4	119.6	C34A—C34—H34	119.5
C4—C4A—C12A	119.0 (2)	C34—C34A—C42A	118.9 (2)
C4—C4A—N5	119.5 (2)	C34—C34A—N35	119.4 (2)
C12A—C4A—N5	121.4 (2)	C42A—C34A—N35	121.7 (2)
C4A—N5—C13	110.8 (2)	C34A—N35—C43	110.28 (19)
C4A—N5—C6	113.32 (19)	C34A—N35—C36	113.46 (17)
C13—N5—C6	107.35 (19)	C43—N35—C36	107.33 (18)
N5—C6—C6A	112.2 (2)	N35—C36—C36A	113.08 (19)
N5—C6—H6A	109.2	N35—C36—H36A	109.0
C6A—C6—H6A	109.2	C36A—C36—H36A	109.0
N5—C6—H6B	109.2	N35—C36—H36B	109.0
C6A—C6—H6B	109.2	C36A—C36—H36B	109.0
H6A—C6—H6B	107.9	H36A—C36—H36B	107.8
C10A—C6A—C7	119.3 (2)	C40A—C36A—C37	118.9 (2)
C10A—C6A—C6	120.1 (2)	C40A—C36A—C36	120.2 (2)
C7—C6A—C6	120.6 (2)	C37—C36A—C36	120.8 (2)
C8—C7—C6A	122.3 (2)	C38—C37—C36A	122.9 (2)
C8—C7—H7	118.9	C38—C37—H37	118.6
C6A—C7—H7	118.9	C36A—C37—H37	118.6
C7—C8—C9	117.3 (2)	C37—C38—C39	116.7 (2)
C7—C8—C18	123.1 (2)	C37—C38—C48	123.3 (2)
C9—C8—C18	119.6 (2)	C39—C38—C48	119.9 (2)
C10—C9—C8	120.9 (2)	C40—C39—C38	121.2 (2)
C10—C9—H9	119.5	C40—C39—H39	119.4
C8—C9—H9	119.5	C38—C39—H39	119.4
C9—C10—C10A	121.2 (2)	C39—C40—C40A	121.1 (2)
C9—C10—H10	119.4	C39—C40—H40	119.4
C10A—C10—H10	119.4	C40A—C40—H40	119.4
C10—C10A—C6A	118.8 (2)	C40—C40A—C36A	118.9 (2)
C10—C10A—N11	119.0 (2)	C40—C40A—N41	119.4 (2)
C6A—C10A—N11	122.2 (2)	C36A—C40A—N41	121.7 (2)
C10A—N11—C13	110.1 (2)	C40A—N41—C43	110.61 (19)
C10A—N11—C12	113.00 (18)	C40A—N41—C42	113.05 (18)
C13—N11—C12	107.82 (19)	C43—N41—C42	107.66 (18)
N11—C12—C12A	112.3 (2)	N41—C42—C42A	112.4 (2)
N11—C12—H12A	109.2	N41—C42—H42A	109.1
C12A—C12—H12A	109.2	C42A—C42—H42A	109.1
N11—C12—H12B	109.2	N41—C42—H42B	109.1
C12A—C12—H12B	109.2	C42A—C42—H42B	109.1
H12A—C12—H12B	107.9	H42A—C42—H42B	107.9
C1—C12A—C4A	119.1 (2)	C31—C42A—C34A	119.1 (2)
C1—C12A—C12	120.2 (2)	C31—C42A—C42	120.3 (2)
C4A—C12A—C12	120.8 (2)	C34A—C42A—C42	120.6 (2)
N5—C13—N11	111.8 (2)	N35—C43—N41	111.99 (17)
N5—C13—H13A	109.3	N35—C43—H43A	109.2
N11—C13—H13A	109.3	N41—C43—H43A	109.2
N5—C13—H13B	109.3	N35—C43—H43B	109.2
N11—C13—H13B	109.3	N41—C43—H43B	109.2
H13A—C13—H13B	107.9	H43A—C43—H43B	107.9
C15—C14—C17	108.2 (2)	C46—C44—C45	111.1 (3)
C15—C14—C16	108.7 (3)	C46—C44—C32	112.5 (3)
C17—C14—C16	109.5 (3)	C45—C44—C32	109.7 (2)
C15—C14—C2	112.1 (2)	C46—C44—C47	107.1 (3)
C17—C14—C2	109.8 (3)	C45—C44—C47	107.0 (3)
C16—C14—C2	108.5 (2)	C32—C44—C47	109.3 (3)
C14—C15—H15A	109.5	C44—C45—H45A	109.5
C14—C15—H15B	109.5	C44—C45—H45B	109.5
H15A—C15—H15B	109.5	H45A—C45—H45B	109.5
C14—C15—H15C	109.5	C44—C45—H45C	109.5
H15A—C15—H15C	109.5	H45A—C45—H45C	109.5
H15B—C15—H15C	109.5	H45B—C45—H45C	109.5
C14—C16—H16A	109.5	C44—C46—H46A	109.5
C14—C16—H16B	109.5	C44—C46—H46B	109.5
H16A—C16—H16B	109.5	H46A—C46—H46B	109.5
C14—C16—H16C	109.5	C44—C46—H46C	109.5
H16A—C16—H16C	109.5	H46A—C46—H46C	109.5
H16B—C16—H16C	109.5	H46B—C46—H46C	109.5
C14—C17—H17A	109.5	C44—C47—H47A	109.5
C14—C17—H17B	109.5	C44—C47—H47B	109.5
H17A—C17—H17B	109.5	H47A—C47—H47B	109.5
C14—C17—H17C	109.5	C44—C47—H47C	109.5
H17A—C17—H17C	109.5	H47A—C47—H47C	109.5
H17B—C17—H17C	109.5	H47B—C47—H47C	109.5
C20—C18—C19	108.6 (2)	C38—C48—C50	112.4 (2)
C20—C18—C21	109.4 (2)	C38—C48—C49	110.7 (2)
C19—C18—C21	107.9 (2)	C50—C48—C49	108.2 (2)
C20—C18—C8	109.38 (19)	C38—C48—C51	108.18 (19)
C19—C18—C8	111.5 (2)	C50—C48—C51	108.3 (2)
C21—C18—C8	109.9 (2)	C49—C48—C51	109.0 (2)
C18—C19—H19A	109.5	C48—C49—H49A	109.5
C18—C19—H19B	109.5	C48—C49—H49B	109.5
H19A—C19—H19B	109.5	H49A—C49—H49B	109.5
C18—C19—H19C	109.5	C48—C49—H49C	109.5
H19A—C19—H19C	109.5	H49A—C49—H49C	109.5
H19B—C19—H19C	109.5	H49B—C49—H49C	109.5
C18—C20—H20A	109.5	C48—C50—H50A	109.5
C18—C20—H20B	109.5	C48—C50—H50B	109.5
H20A—C20—H20B	109.5	H50A—C50—H50B	109.5
C18—C20—H20C	109.5	C48—C50—H50C	109.5
H20A—C20—H20C	109.5	H50A—C50—H50C	109.5
H20B—C20—H20C	109.5	H50B—C50—H50C	109.5
C18—C21—H21A	109.5	C48—C51—H51A	109.5
C18—C21—H21B	109.5	C48—C51—H51B	109.5
H21A—C21—H21B	109.5	H51A—C51—H51B	109.5
C18—C21—H21C	109.5	C48—C51—H51C	109.5
H21A—C21—H21C	109.5	H51A—C51—H51C	109.5
H21B—C21—H21C	109.5	H51B—C51—H51C	109.5

C12A—C1—C2—C3	−0.7 (4)	C42A—C31—C32—C33	0.6 (4)
C12A—C1—C2—C14	177.5 (2)	C42A—C31—C32—C44	−179.8 (2)
C1—C2—C3—C4	2.4 (4)	C31—C32—C33—C34	0.2 (4)
C14—C2—C3—C4	−175.8 (2)	C44—C32—C33—C34	−179.4 (2)
C2—C3—C4—C4A	−1.3 (4)	C32—C33—C34—C34A	−0.6 (4)
C3—C4—C4A—C12A	−1.7 (3)	C33—C34—C34A—C42A	0.3 (3)
C3—C4—C4A—N5	175.8 (2)	C33—C34—C34A—N35	179.5 (2)
C4—C4A—N5—C13	−162.8 (2)	C34—C34A—N35—C43	−161.38 (19)
C12A—C4A—N5—C13	14.6 (3)	C42A—C34A—N35—C43	17.8 (3)
C4—C4A—N5—C6	76.5 (3)	C34—C34A—N35—C36	78.2 (2)
C12A—C4A—N5—C6	−106.1 (3)	C42A—C34A—N35—C36	−102.6 (2)
C4A—N5—C6—C6A	77.4 (3)	C34A—N35—C36—C36A	79.0 (2)
C13—N5—C6—C6A	−45.2 (2)	C43—N35—C36—C36A	−43.1 (2)
N5—C6—C6A—C10A	9.2 (3)	N35—C36—C36A—C40A	7.0 (3)
N5—C6—C6A—C7	−170.1 (2)	N35—C36—C36A—C37	−171.3 (2)
C10A—C6A—C7—C8	−2.3 (3)	C40A—C36A—C37—C38	−2.3 (3)
C6—C6A—C7—C8	177.0 (2)	C36—C36A—C37—C38	176.1 (2)
C6A—C7—C8—C9	−2.1 (3)	C36A—C37—C38—C39	−1.4 (3)
C6A—C7—C8—C18	177.1 (2)	C36A—C37—C38—C48	176.0 (2)
C7—C8—C9—C10	3.9 (3)	C37—C38—C39—C40	2.9 (4)
C18—C8—C9—C10	−175.4 (2)	C48—C38—C39—C40	−174.7 (2)
C8—C9—C10—C10A	−1.2 (4)	C38—C39—C40—C40A	−0.6 (4)
C9—C10—C10A—C6A	−3.4 (3)	C39—C40—C40A—C36A	−3.2 (4)
C9—C10—C10A—N11	175.1 (2)	C39—C40—C40A—N41	174.7 (2)
C7—C6A—C10A—C10	5.1 (3)	C37—C36A—C40A—C40	4.5 (4)
C6—C6A—C10A—C10	−174.3 (2)	C36—C36A—C40A—C40	−173.9 (2)
C7—C6A—C10A—N11	−173.4 (2)	C37—C36A—C40A—N41	−173.28 (19)
C6—C6A—C10A—N11	7.3 (3)	C36—C36A—C40A—N41	8.3 (4)
C10—C10A—N11—C13	−164.1 (2)	C40—C40A—N41—C43	−163.4 (2)
C6A—C10A—N11—C13	14.3 (3)	C36A—C40A—N41—C43	14.4 (3)
C10—C10A—N11—C12	75.2 (3)	C40—C40A—N41—C42	75.8 (3)
C6A—C10A—N11—C12	−106.4 (2)	C36A—C40A—N41—C42	−106.4 (3)
C10A—N11—C12—C12A	77.1 (3)	C40A—N41—C42—C42A	77.6 (2)
C13—N11—C12—C12A	−44.8 (3)	C43—N41—C42—C42A	−44.9 (2)
C2—C1—C12A—C4A	−2.2 (4)	C32—C31—C42A—C34A	−0.9 (3)
C2—C1—C12A—C12	177.1 (2)	C32—C31—C42A—C42	177.4 (2)
C4—C4A—C12A—C1	3.3 (3)	C34—C34A—C42A—C31	0.5 (3)
N5—C4A—C12A—C1	−174.1 (2)	N35—C34A—C42A—C31	−178.67 (19)
C4—C4A—C12A—C12	−175.9 (2)	C34—C34A—C42A—C42	−177.9 (2)
N5—C4A—C12A—C12	6.7 (3)	N35—C34A—C42A—C42	3.0 (3)
N11—C12—C12A—C1	−169.8 (2)	N41—C42—C42A—C31	−166.85 (19)
N11—C12—C12A—C4A	9.4 (3)	N41—C42—C42A—C34A	11.5 (3)
C4A—N5—C13—N11	−53.3 (3)	C34A—N35—C43—N41	−54.7 (2)
C6—N5—C13—N11	70.9 (2)	C36—N35—C43—N41	69.4 (2)
C10A—N11—C13—N5	−53.9 (3)	C40A—N41—C43—N35	−54.2 (3)
C12—N11—C13—N5	69.8 (3)	C42—N41—C43—N35	69.7 (2)
C1—C2—C14—C15	9.4 (4)	C31—C32—C44—C46	174.2 (3)
C3—C2—C14—C15	−172.5 (2)	C33—C32—C44—C46	−6.1 (4)
C1—C2—C14—C17	129.7 (3)	C31—C32—C44—C45	−61.7 (4)
C3—C2—C14—C17	−52.2 (3)	C33—C32—C44—C45	118.0 (3)
C1—C2—C14—C16	−110.6 (3)	C31—C32—C44—C47	55.3 (4)
C3—C2—C14—C16	67.5 (4)	C33—C32—C44—C47	−125.0 (3)
C7—C8—C18—C20	105.7 (3)	C37—C38—C48—C50	8.5 (3)
C9—C8—C18—C20	−75.0 (3)	C39—C38—C48—C50	−174.1 (2)
C7—C8—C18—C19	−14.5 (3)	C37—C38—C48—C49	129.6 (2)
C9—C8—C18—C19	164.7 (2)	C39—C38—C48—C49	−53.0 (3)
C7—C8—C18—C21	−134.2 (2)	C37—C38—C48—C51	−111.0 (2)
C9—C8—C18—C21	45.1 (3)	C39—C38—C48—C51	66.4 (3)

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