{Tris[3-(adamantan-1-yl)-5-iso­propyl­pyrazol-1-yl-[kappa]N²]hydro­borato}thallium(I): the scorpionate with the most bulk?

In the thallium(I) complex, [Tl(C₄₈H₇₀BN₆)], of tris[3-(ada­mantan-1-yl)-5-iso­propyl­pyrazol-1-yl]hydro­borate, the most hindered scorpionate ligand, the Tl^I ion is coordinated by three N atoms from the anionic tridentate chelating ligand [average Tl-N bond length = 2.522 (4) Å] in a distorted trigonal-pyramidal environment [average N-Tl-N angle around the Tl^I ion = 76.4 (1)°]. This coordination geometry is compared with that of the reported Tl^I complex of the super-hindered tris­(7-tert-butyl­indazol-2-yl)hydro­borate ligand.

S1. Introduction

Tris(pyrazolyl)borate ligands have given rise to a tremendous amount of chemistry with amazing diversity and have been considered as one of the most useful ligands in current coordination chemistry. Their versatility derives from the different steric and electronic effects that can be introduced by modifying the number and position of substituents in the pyrazolyl rings that allows fine-tuning of the open-coordination site and the reactivity at the metal centers. The late Professor Swiatoslaw Trofimenko first published this ligand system in 1966 (Trofimenko, 1966). In 1986, bulkier substituents were introduced in the 3-position of the pyrazolyl rings, {HB(3-Rpz)₃}^- (R = Ph, t-Bu; Calabrese et al., 1986; Trofimenko et al., 1987). Later, many other substituents, aliphatic or aromatic groups, in the 3- and/or 5- (and/or 4-) position(s) were inserted to explore novel coordination chemistry (Trofimenko, 1999; Pettinari, 2008) afforded by the increased steric bulk.

S2. Experimental

S2.1. Synthesis and crystallization

The title complex, [Tl{HB(3—Ad-5-i-Prpz)₃}], (I), was prepared by metathesis from the potassium ligand salt. K[HB(3—Ad-5-i-Prpz)₃] (221 mg, 0.28 mmol) in tetra­hydro­furan (10 ml) was added to TlPF₆ (98.4 mg, 0.28 mmol) in tetra­hydro­furan (10 ml) and the stirred at room temperature overnight under an inert atmosphere. The solvent was then removed under reduced pressure. The resulting colorless solid was extracted into di­chloro­methane and filtered over Celite. The filtrate was concenterated and cooled to 243 K to obtain colorless crystals (yield 173.9 mg, 64%) of (I). Single crystals were obtained by slow evaporation from a saturated di­chloro­methane–heptane (1/2 v/v) solution. Elemental analyses calculated for C₄₈H₇₀BN₆Tl: C 60.92, H 7.46, N 8.88%; found: C 60.89, H 7.36, N 8.93 %. IR (KBr disc, ν, cm^-1): 2962 (s), 2901 (s), 2845 (s), 2539 (m), 1524 (m), 1456 (m), 1167 (m), 1055 (m), 783 (m). ¹H NMR (CDCl₃, 125 MHz): δ 1.04 [d, J = 7.0 Hz, 18H, CH(CH₃)₂], 1.75 (br s, 6H, Ad-δ), 1.96 (br s, 6H, Ad-β), 2.04 (br s, 3H, Ad-γ), 3.35 [sept, J = 7.0 Hz, 3H, CH(CH₃)₂], 5.84 [s, 3H, 4-H(pz)]. ¹³C NMR (CDCl₃, 500 MHz): δ 23.3 [s, CH(CH₃)₂], 26.25 [s, CH(CH₃)₂], 28.9 (s, Ad-γ), 34.3 (s, Ad-α), 37.0 (s, Ad-δ), 43.4 (br s, Ad-β), 93.3 (s, pz-4C), 155.3 (s, pz-3C), 162.6 (s, pz-5C).

S2.2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were placed in calculated idealized geometry (0.98–1.00 Å), treated as rigid groups, and constrained with U_iso(H) = 1.2 or 1.5 times U_eq of the attached non-H atom.

S3. Results and discussion

The steric hindrances at the metal centers by can be adjusted by using a similar strategy as seen in the synthesis of [HB{3,5-(i-Pr)₂pz}₃]^- [namely tris­(3,5-diiso­propyl-1-pyrazolyl)hydro­borate(1-)] (Kitajima et al., 1989) which was prepared to afford binuclear peroxidocopper(II) complexes (Kitajima et al., 1992; Baldwin et al., 1992) as models for oxy-hemocyanin (Fig. 1). Expanding this ligand system, we introduced a tert-butyl group in the 3-position of the pyrazolyl ring and obtained [HB(3-t-Bu-5-i-Prpz)₃]^- [tris­(3-tert-butyl-5-iso­propyl­pyrazol-1-yl)hydro­borate(1-)], in order to study mononuclear superoxidocopper(II) and mononuclear hydroxidocopper(II) complexes (Fujisawa et al., 1994, 2000), such as [Cu(O₂){HB(3-t-Bu-5-i-Prpz)₃}] and [Cu(OH){HB(3-t-Bu-5-i-Prpz)₃}]. However, over the course of this study, it was determined that there was some contamination by a dimeric [{Cu[HB(3-t-Bu-5-i-Prpz)₃]}₂(µ-O₂)] component in solution (Chen et al., 2003). Therefore, a much bulkier ligand was prepared, viz. [HB(3—Ad-5-i-Prpz)₃]^- {tris­[3-(adamantan-1-yl)-5-iso­propyl-1-pyrazolyl]hydro­borate(1-)}, to combat dimer formation. Moreover, structural differences were compared between tert-butyl and adamantyl groups in the chloridocopper(II) complexes [CuCl{HB(3-t-Bu-5-i-Prpz)₃}] versus [CuCl{HB(3—Ad-5-i-Prpz)₃}]. Based on this comparison, we claimed this adamantyl-substituted ligand to be `the most hindered Tp ligand' (Fujisawa et al., 2004).

After we published this manuscript, Professor Trofimenko sent an e-mail message asking, `I noted your communication (Fujisawa et al., 2004) reporting `the most hindered Tp ligand'. Have you ever compared its steric hindrance with that of the super-hindered Tp ligand reported in 1996 (Rheingold et al., 1996)' My answer was `No' at that point. So he sent another message, `Would you be inter­ested to try my super-hindered ligand in your system. If so, I will be happy to send you a sample of this ligand.' Since a comparison could be valuable, I replied, `Please send it.' He kindly sent samples of both the potassium and thallium salts of Tp^3Bo,7But, K(C₃₃H₄₀BN₆B) and [Tl(C₃₃H₄₀BN₆)], (II). Unfortunately, neither salt produced pure metathesis products with copper(II) chloride dihydrate. Instead, we obtained what appeared to be reduction decomposition. Therefore, no direct comparison of the steric hindrance could be made against our previously reported [CuCl{HB(3—Ad-5-i-Prpz)₃}] (vide supra). After many years, we finally obtained single crystals of the title compound allowing a direct comparison with compound (II). In order to get the best comparison, we also prepared single crystals of (II) and collected diffraction data under the same experimental conditions as for (I). The parameters we obtained for (II) were essentially identical with those previously reported (Rheingold et al., 1996).

As shown in Fig. 2, the Tl^I ion has distorted trigonal–pyramidal environment. The average N—Tl^I—N angle between adjacent coordinated pyrazole-ring N atoms is 76.4 (1)°, while that of (II) is 79.1 (1)°. The average Tl^I—N distance is 2.522 (4) Å, while that of (II) is 2.6757 (6) Å. Moreover, the average B—N distance is 1.554 (6) Å, while that of (II) is 1.543 (9) Å. Thus, the coordination site of (II) is wider than that of (I). However, the distance between the Tl^I atom and the plane formed by atoms N11, N21, and N31 of (I) is 1.800 (2) Å, whereas the analogous distance in (II) is 1.768 (1) Å. This suggests that the metal ion is more tightly coordinated, apparently an electronic effect, in (II) than in (I). This might explain the observed difficulty in preparing copper(II) complexes with Tp^3Bo,7But. This observation is supported by the calculated cone angle, derived solely from the solid-state atomic coordinates (Manz et al., 2007), with values of 262.22 (11) and 241.21 (3)° in (I) and (II), respectively. We also observe that the thallium(I) ion of (I) could be easily replaced by transition metals in contrast to (II). This different lability results from the change of the ligand framework from pyrazole to indazole. Therefore, our adamantyl-substituted Tp ligand remains as the most hindered scorpionate. The Tp^3Bo,7But ligand in itself is also super-hindered, however, its potential as ligand for transition metals could be hampered by the tendency to promote tighter coordination. We are currently exploring these fruitful and bulky scorpionates that display facile control of steric and electronic configurations.

Related literature

For related literature, see: Baldwin et al. (1992); Calabrese et al. (1986); Chen et al. (2003); Fujisawa et al. (1994, 2000, 2004); Kitajima et al. (1989, 1992); Manz et al. (2007); Pettinari (2008); Rheingold et al. (1996); Trofimenko (1966, 1999); Trofimenko et al. (1987).

Computing details

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear (Rigaku, 2008); data reduction: CrystalClear (Rigaku, 2008); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); software used to prepare material for publication: CrystalStructure (Rigaku, 2010).

Figures

Schematic drawing of the scorpionate ligands discussed in this paper.

The molecular structure of [Tl{HB(3—Ad-5 - i-Prpz)3}], (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.

{Tris[3-(adamantan-1-yl)-5-isopropylpyrazol-1-yl-κN²]hydroborato}thallium(I)

Crystal data

[Tl(C48H70BN6)]	F(000) = 1944.00
Mr = 946.30	Dx = 1.401 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: -P 2yn	Cell parameters from 13331 reflections
a = 14.6558 (17) Å	θ = 3.0–27.5°
b = 11.6017 (13) Å	µ = 3.64 mm^−1
c = 27.148 (4) Å	T = 198 K
β = 103.6620 (14)°	Prism, colorless
V = 4485.4 (9) Å^3	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection

Rigaku Mercury70 diffractometer	9490 reflections with F^2 > 2σ(F^2)
Detector resolution: 7.314 pixels mm^-1	Rint = 0.022
ω scans	θmax = 27.5°
Absorption correction: multi-scan (REQAB; Rigaku, 1998)	h = −19→14
Tmin = 0.227, Tmax = 0.403	k = −12→15
33700 measured reflections	l = −33→35
10228 independent reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 0.99	w = 1/[σ^2(Fo^2) + (0.1P)^2] where P = (Fo^2 + 2Fc^2)/3
10228 reflections	(Δ/σ)max = 0.002
505 parameters	Δρmax = 0.90 e Å^−3
0 restraints	Δρmin = −1.76 e Å^−3
Primary atom site location: structure-invariant direct methods

Special details

Refinement. Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

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

	x	y	z	Uiso*/Ueq
Tl1	0.678187 (9)	0.222734 (11)	0.874465 (5)	0.02179 (7)
N11	0.5759 (2)	0.3977 (3)	0.86077 (11)	0.0210 (6)
N12	0.6029 (2)	0.4931 (3)	0.89066 (11)	0.0195 (6)
N21	0.7858 (3)	0.3895 (3)	0.86776 (12)	0.0231 (6)
N22	0.7783 (2)	0.4939 (3)	0.89098 (11)	0.0202 (6)
N31	0.7131 (3)	0.3104 (3)	0.96260 (11)	0.0215 (6)
N32	0.7256 (2)	0.4271 (3)	0.96903 (11)	0.0200 (6)
C130	0.4294 (3)	0.3175 (3)	0.80374 (13)	0.0214 (7)
C131	0.4816 (4)	0.2775 (4)	0.76401 (16)	0.0292 (9)
C132	0.4112 (3)	0.2141 (3)	0.83527 (16)	0.0277 (9)
C133	0.3344 (3)	0.3669 (4)	0.77607 (16)	0.0306 (8)
C134	0.4244 (4)	0.1846 (5)	0.73001 (17)	0.0384 (10)
C135	0.4073 (4)	0.0827 (4)	0.76180 (19)	0.0419 (11)
C136	0.3535 (4)	0.1229 (4)	0.80081 (18)	0.0368 (10)
C137	0.2594 (4)	0.1744 (4)	0.7731 (2)	0.0425 (11)
C138	0.2756 (4)	0.2765 (4)	0.7411 (2)	0.0424 (12)
C139	0.3294 (5)	0.2362 (6)	0.70230 (19)	0.0484 (13)
C140	0.4844 (3)	0.4093 (3)	0.83896 (13)	0.0214 (7)
C150	0.4515 (3)	0.5131 (4)	0.85443 (14)	0.0250 (7)
C160	0.5276 (3)	0.5639 (3)	0.88733 (13)	0.0201 (7)
C170	0.5305 (3)	0.6752 (3)	0.91583 (14)	0.0246 (7)
C180	0.5206 (4)	0.6514 (4)	0.96972 (16)	0.0373 (10)
C190	0.4551 (4)	0.7584 (4)	0.8878 (2)	0.0407 (11)
C230	0.8869 (3)	0.2973 (4)	0.81775 (14)	0.0230 (7)
C231	0.8058 (3)	0.2576 (4)	0.77386 (15)	0.0275 (8)
C232	0.9186 (3)	0.1964 (4)	0.85496 (14)	0.0287 (8)
C233	0.9703 (3)	0.3303 (4)	0.79540 (16)	0.0332 (9)
C234	0.8352 (3)	0.1527 (4)	0.74683 (16)	0.0348 (9)
C235	0.8643 (4)	0.0545 (4)	0.78446 (17)	0.0380 (10)
C236	0.9479 (4)	0.0921 (4)	0.82714 (18)	0.0378 (10)
C237	1.0296 (4)	0.1283 (5)	0.80477 (19)	0.0436 (11)
C238	1.0009 (4)	0.2263 (5)	0.76785 (19)	0.0397 (12)
C239	0.9186 (4)	0.1877 (5)	0.72467 (17)	0.0424 (11)
C240	0.8577 (3)	0.3979 (3)	0.84541 (13)	0.0219 (7)
C250	0.8967 (3)	0.5090 (3)	0.85372 (14)	0.0255 (8)
C260	0.8465 (3)	0.5666 (3)	0.88350 (13)	0.0227 (7)
C270	0.8604 (3)	0.6878 (4)	0.90385 (15)	0.0267 (8)
C280	0.8044 (5)	0.7766 (4)	0.8674 (2)	0.0486 (14)
C290	0.9650 (4)	0.7201 (4)	0.9169 (3)	0.0531 (16)
C330	0.7391 (3)	0.1337 (3)	1.01505 (13)	0.0207 (7)
C331	0.8116 (3)	0.0749 (3)	0.99069 (14)	0.0251 (7)
C332	0.6412 (3)	0.0834 (3)	0.99163 (15)	0.0261 (8)
C333	0.7647 (3)	0.1027 (3)	1.07242 (14)	0.0280 (8)
C334	0.8093 (3)	−0.0566 (4)	0.99784 (15)	0.0322 (9)
C335	0.7118 (4)	−0.1027 (4)	0.97381 (16)	0.0360 (10)
C336	0.6395 (3)	−0.0469 (4)	0.99830 (17)	0.0340 (9)
C337	0.6651 (4)	−0.0755 (4)	1.05563 (19)	0.0426 (11)
C338	0.7623 (4)	−0.0284 (4)	1.07959 (16)	0.0364 (10)
C339	0.8346 (4)	−0.0841 (4)	1.05492 (17)	0.0388 (10)
C340	0.7409 (3)	0.2626 (3)	1.00804 (14)	0.0198 (7)
C350	0.7709 (3)	0.3479 (3)	1.04490 (14)	0.0249 (7)
C360	0.7614 (3)	0.4511 (3)	1.01904 (13)	0.0224 (7)
C370	0.7915 (3)	0.5681 (3)	1.03983 (14)	0.0276 (8)
C380	0.8947 (4)	0.5858 (4)	1.04030 (19)	0.0417 (11)
C390	0.7747 (5)	0.5837 (4)	1.09298 (18)	0.0475 (13)
B1	0.7042 (3)	0.5110 (4)	0.92299 (14)	0.0196 (7)
H1	0.7096	0.5917	0.9362	0.0235*
H2	0.4918	0.3439	0.7430	0.0350*
H3	0.5438	0.2460	0.7812	0.0350*
H4	0.4718	0.1805	0.8536	0.0333*
H5	0.3769	0.2399	0.8606	0.0333*
H6	0.3445	0.4344	0.7557	0.0368*
H7	0.2998	0.3932	0.8012	0.0368*
H8	0.4594	0.1583	0.7046	0.0461*
H9	0.4681	0.0484	0.7795	0.0503*
H10	0.3705	0.0230	0.7396	0.0503*
H11	0.3423	0.0558	0.8217	0.0441*
H12	0.2217	0.1152	0.7511	0.0509*
H13	0.2241	0.1999	0.7981	0.0509*
H14	0.2140	0.3106	0.7233	0.0509*
H15	0.3399	0.3023	0.6812	0.0581*
H16	0.2922	0.1775	0.6797	0.0581*
H17	0.3894	0.5428	0.8444	0.0300*
H18	0.5932	0.7117	0.9181	0.0295*
H19	0.5715	0.6005	0.9870	0.0447*
H20	0.4600	0.6142	0.9684	0.0447*
H21	0.5239	0.7242	0.9883	0.0447*
H22	0.3929	0.7239	0.8847	0.0488*
H23	0.4649	0.7739	0.8539	0.0488*
H24	0.4590	0.8307	0.9068	0.0488*
H25	0.7506	0.2374	0.7873	0.0330*
H26	0.7874	0.3215	0.7493	0.0330*
H27	0.9722	0.2213	0.8824	0.0344*
H28	0.8665	0.1740	0.8705	0.0344*
H29	1.0235	0.3561	0.8229	0.0398*
H30	0.9522	0.3950	0.7713	0.0398*
H31	0.7815	0.1275	0.7188	0.0418*
H32	0.8821	−0.0136	0.7668	0.0456*
H33	0.8108	0.0326	0.7990	0.0456*
H34	0.9676	0.0271	0.8515	0.0453*
H35	1.0832	0.1526	0.8324	0.0523*
H36	1.0500	0.0619	0.7872	0.0523*
H37	1.0553	0.2489	0.7535	0.0476*
H38	0.9381	0.1216	0.7065	0.0508*
H39	0.8998	0.2516	0.7002	0.0508*
H40	0.9474	0.5388	0.8414	0.0306*
H41	0.8380	0.6906	0.9359	0.0320*
H42	0.7374	0.7580	0.8606	0.0584*
H43	0.8248	0.7754	0.8355	0.0584*
H44	0.8151	0.8535	0.8826	0.0584*
H45	0.9893	0.7156	0.8863	0.0637*
H46	0.9998	0.6665	0.9425	0.0637*
H47	0.9726	0.7988	0.9304	0.0637*
H48	0.8751	0.1045	1.0065	0.0301*
H49	0.7975	0.0934	0.9541	0.0301*
H50	0.5945	0.1192	1.0079	0.0313*
H51	0.6233	0.1023	0.9550	0.0313*
H52	0.8282	0.1321	1.0883	0.0336*
H53	0.7195	0.1398	1.0894	0.0336*
H54	0.8561	−0.0936	0.9814	0.0386*
H55	0.7108	−0.1873	0.9783	0.0432*
H56	0.6960	−0.0859	0.9370	0.0432*
H57	0.5755	−0.0773	0.9823	0.0408*
H58	0.6183	−0.0407	1.0721	0.0512*
H59	0.6643	−0.1601	1.0605	0.0512*
H60	0.7784	−0.0466	1.1166	0.0437*
H61	0.8351	−0.1686	1.0601	0.0466*
H62	0.8980	−0.0540	1.0707	0.0466*
H63	0.7932	0.3368	1.0804	0.0299*
H64	0.7537	0.6271	1.0169	0.0331*
H65	0.9034	0.5781	1.0057	0.0501*
H66	0.9327	0.5277	1.0621	0.0501*
H67	0.9144	0.6629	1.0533	0.0501*
H68	0.8105	0.5255	1.1158	0.0570*
H69	0.7076	0.5747	1.0916	0.0570*
H70	0.7953	0.6608	1.1056	0.0570*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Tl1	0.02389 (11)	0.01620 (10)	0.02477 (10)	−0.00004 (4)	0.00470 (7)	−0.00422 (4)
N11	0.0244 (15)	0.0165 (14)	0.0216 (14)	0.0007 (12)	0.0040 (11)	−0.0042 (11)
N12	0.0213 (15)	0.0158 (13)	0.0216 (13)	−0.0026 (11)	0.0051 (11)	−0.0023 (11)
N21	0.0250 (16)	0.0159 (13)	0.0307 (16)	−0.0024 (12)	0.0112 (13)	−0.0089 (12)
N22	0.0232 (15)	0.0132 (13)	0.0246 (14)	−0.0003 (11)	0.0063 (11)	−0.0042 (11)
N31	0.0249 (16)	0.0120 (13)	0.0273 (15)	−0.0004 (12)	0.0056 (12)	−0.0055 (12)
N32	0.0227 (15)	0.0133 (13)	0.0229 (14)	−0.0002 (11)	0.0031 (11)	−0.0039 (11)
C130	0.0217 (17)	0.0196 (16)	0.0230 (16)	−0.0034 (13)	0.0056 (13)	−0.0009 (13)
C131	0.026 (2)	0.034 (3)	0.029 (2)	−0.0051 (15)	0.0099 (17)	−0.0069 (14)
C132	0.029 (3)	0.0242 (19)	0.032 (2)	−0.0054 (14)	0.0113 (17)	0.0022 (14)
C133	0.0240 (19)	0.0241 (18)	0.040 (2)	−0.0025 (15)	−0.0011 (16)	−0.0025 (16)
C134	0.041 (3)	0.043 (3)	0.032 (2)	−0.005 (2)	0.0088 (18)	−0.0184 (19)
C135	0.043 (3)	0.028 (2)	0.051 (3)	−0.0009 (19)	0.004 (2)	−0.0147 (19)
C136	0.039 (3)	0.0240 (19)	0.048 (3)	−0.0133 (17)	0.0122 (19)	−0.0039 (18)
C137	0.029 (3)	0.039 (3)	0.059 (3)	−0.0166 (19)	0.008 (2)	−0.015 (3)
C138	0.028 (3)	0.039 (3)	0.049 (3)	−0.0003 (17)	−0.014 (2)	−0.0126 (19)
C139	0.046 (4)	0.060 (4)	0.031 (3)	−0.011 (3)	−0.007 (2)	−0.007 (3)
C140	0.0200 (17)	0.0189 (16)	0.0257 (16)	−0.0031 (13)	0.0066 (13)	0.0001 (13)
C150	0.0175 (17)	0.0247 (17)	0.0324 (19)	−0.0020 (14)	0.0051 (14)	−0.0029 (14)
C160	0.0211 (17)	0.0172 (15)	0.0229 (16)	−0.0014 (13)	0.0069 (13)	−0.0019 (13)
C170	0.0230 (18)	0.0171 (16)	0.0343 (19)	0.0010 (13)	0.0082 (14)	−0.0053 (14)
C180	0.050 (3)	0.030 (2)	0.035 (2)	0.0019 (19)	0.0156 (19)	−0.0081 (17)
C190	0.042 (3)	0.026 (2)	0.052 (3)	0.015 (2)	0.007 (3)	−0.006 (2)
C230	0.0193 (17)	0.0288 (17)	0.0211 (16)	0.0020 (15)	0.0050 (14)	−0.0037 (14)
C231	0.0229 (19)	0.0350 (19)	0.0241 (18)	−0.0019 (16)	0.0042 (15)	−0.0059 (16)
C232	0.025 (2)	0.036 (2)	0.0222 (17)	0.0067 (17)	0.0014 (14)	0.0007 (16)
C233	0.024 (2)	0.042 (3)	0.036 (2)	−0.0014 (17)	0.0128 (16)	−0.0050 (18)
C234	0.027 (2)	0.045 (3)	0.032 (2)	0.0031 (18)	0.0047 (16)	−0.0159 (18)
C235	0.038 (3)	0.031 (2)	0.046 (3)	0.0041 (18)	0.0123 (19)	−0.0134 (18)
C236	0.035 (3)	0.033 (3)	0.045 (3)	0.0111 (18)	0.0084 (19)	−0.0036 (18)
C237	0.031 (3)	0.050 (3)	0.050 (3)	0.016 (2)	0.010 (2)	−0.013 (3)
C238	0.026 (3)	0.058 (4)	0.039 (3)	0.0055 (18)	0.015 (2)	−0.0129 (19)
C239	0.039 (3)	0.060 (3)	0.031 (2)	0.007 (3)	0.0144 (19)	−0.012 (3)
C240	0.0177 (16)	0.0243 (17)	0.0222 (16)	0.0008 (13)	0.0019 (13)	−0.0020 (13)
C250	0.0246 (18)	0.0211 (17)	0.0324 (19)	−0.0027 (14)	0.0098 (15)	0.0011 (14)
C260	0.0197 (17)	0.0220 (17)	0.0255 (17)	−0.0032 (13)	0.0031 (13)	0.0005 (14)
C270	0.0276 (19)	0.0207 (17)	0.0314 (18)	−0.0063 (15)	0.0064 (15)	−0.0029 (15)
C280	0.067 (4)	0.025 (3)	0.043 (3)	0.0055 (19)	−0.008 (3)	−0.0023 (17)
C290	0.033 (3)	0.034 (3)	0.091 (5)	−0.0116 (18)	0.012 (3)	−0.021 (3)
C330	0.0250 (18)	0.0141 (15)	0.0225 (16)	0.0006 (13)	0.0044 (13)	−0.0024 (12)
C331	0.0250 (18)	0.0200 (17)	0.0302 (18)	0.0048 (14)	0.0065 (14)	−0.0010 (14)
C332	0.0247 (19)	0.0202 (17)	0.0334 (19)	−0.0016 (14)	0.0067 (15)	0.0011 (14)
C333	0.040 (3)	0.0199 (17)	0.0234 (17)	0.0046 (15)	0.0063 (15)	0.0005 (14)
C334	0.041 (3)	0.0202 (18)	0.036 (2)	0.0094 (16)	0.0095 (18)	−0.0013 (15)
C335	0.057 (3)	0.0140 (17)	0.035 (2)	−0.0010 (17)	0.0070 (19)	−0.0054 (15)
C336	0.036 (3)	0.0230 (19)	0.042 (3)	−0.0062 (16)	0.0080 (18)	0.0015 (16)
C337	0.058 (3)	0.027 (2)	0.047 (3)	−0.003 (2)	0.019 (3)	0.0104 (19)
C338	0.055 (3)	0.027 (2)	0.0267 (19)	0.0072 (19)	0.0086 (19)	0.0091 (16)
C339	0.053 (3)	0.0206 (19)	0.039 (3)	0.0145 (18)	0.003 (2)	0.0055 (16)
C340	0.0227 (18)	0.0154 (15)	0.0224 (17)	0.0019 (13)	0.0074 (14)	−0.0004 (13)
C350	0.030 (2)	0.0184 (16)	0.0229 (16)	0.0013 (14)	−0.0012 (14)	−0.0017 (14)
C360	0.0283 (19)	0.0161 (16)	0.0213 (16)	−0.0010 (14)	0.0027 (14)	−0.0031 (13)
C370	0.038 (3)	0.0169 (16)	0.0239 (17)	−0.0012 (15)	−0.0011 (15)	−0.0062 (14)
C380	0.040 (3)	0.023 (2)	0.057 (3)	−0.0047 (18)	0.000 (2)	−0.0080 (19)
C390	0.082 (4)	0.028 (3)	0.035 (3)	−0.009 (3)	0.019 (3)	−0.0148 (18)
B1	0.0191 (18)	0.0160 (16)	0.0227 (17)	−0.0014 (14)	0.0032 (14)	−0.0029 (14)

Geometric parameters (Å, º)

Tl1—N11	2.498 (3)	C131—H3	0.990
Tl1—N21	2.530 (4)	C132—H4	0.990
Tl1—N31	2.538 (3)	C132—H5	0.990
N11—N12	1.375 (4)	C133—H6	0.990
N11—C140	1.339 (5)	C133—H7	0.990
N12—C160	1.361 (5)	C134—H8	1.000
N12—B1	1.550 (5)	C135—H9	0.990
N21—N22	1.383 (5)	C135—H10	0.990
N21—C240	1.338 (6)	C136—H11	1.000
N22—C260	1.359 (5)	C137—H12	0.990
N22—B1	1.556 (6)	C137—H13	0.990
N31—N32	1.372 (4)	C138—H14	1.000
N31—C340	1.326 (5)	C139—H15	0.990
N32—C360	1.364 (5)	C139—H16	0.990
N32—B1	1.556 (5)	C150—H17	0.950
C130—C131	1.534 (7)	C170—H18	1.000
C130—C132	1.533 (6)	C180—H19	0.980
C130—C133	1.529 (5)	C180—H20	0.980
C130—C140	1.529 (5)	C180—H21	0.980
C131—C134	1.533 (6)	C190—H22	0.980
C132—C136	1.528 (6)	C190—H23	0.980
C133—C138	1.535 (6)	C190—H24	0.980
C134—C135	1.519 (7)	C231—H25	0.990
C134—C139	1.539 (8)	C231—H26	0.990
C135—C136	1.535 (8)	C232—H27	0.990
C136—C137	1.528 (7)	C232—H28	0.990
C137—C138	1.519 (8)	C233—H29	0.990
C138—C139	1.531 (9)	C233—H30	0.990
C140—C150	1.399 (6)	C234—H31	1.000
C150—C160	1.385 (5)	C235—H32	0.990
C160—C170	1.501 (5)	C235—H33	0.990
C170—C180	1.529 (6)	C236—H34	1.000
C170—C190	1.528 (6)	C237—H35	0.990
C230—C231	1.541 (5)	C237—H36	0.990
C230—C232	1.544 (6)	C238—H37	1.000
C230—C233	1.537 (7)	C239—H38	0.990
C230—C240	1.504 (6)	C239—H39	0.990
C231—C234	1.535 (7)	C250—H40	0.950
C232—C236	1.540 (7)	C270—H41	1.000
C233—C238	1.541 (7)	C280—H42	0.980
C234—C235	1.523 (7)	C280—H43	0.980
C234—C239	1.540 (8)	C280—H44	0.980
C235—C236	1.537 (6)	C290—H45	0.980
C236—C237	1.524 (8)	C290—H46	0.980
C237—C238	1.509 (7)	C290—H47	0.980
C238—C239	1.537 (7)	C331—H48	0.990
C240—C250	1.406 (5)	C331—H49	0.990
C250—C260	1.386 (6)	C332—H50	0.990
C260—C270	1.506 (6)	C332—H51	0.990
C270—C280	1.527 (7)	C333—H52	0.990
C270—C290	1.536 (7)	C333—H53	0.990
C330—C331	1.537 (6)	C334—H54	1.000
C330—C332	1.540 (5)	C335—H55	0.990
C330—C333	1.556 (5)	C335—H56	0.990
C330—C340	1.509 (5)	C336—H57	1.000
C331—C334	1.539 (6)	C337—H58	0.990
C332—C336	1.524 (6)	C337—H59	0.990
C333—C338	1.534 (6)	C338—H60	1.000
C334—C335	1.521 (6)	C339—H61	0.990
C334—C339	1.539 (6)	C339—H62	0.990
C335—C336	1.522 (7)	C350—H63	0.950
C336—C337	1.548 (7)	C370—H64	1.000
C337—C338	1.521 (7)	C380—H65	0.980
C338—C339	1.525 (8)	C380—H66	0.980
C340—C350	1.402 (5)	C380—H67	0.980
C350—C360	1.378 (5)	C390—H68	0.980
C360—C370	1.495 (5)	C390—H69	0.980
C370—C380	1.524 (7)	C390—H70	0.980
C370—C390	1.531 (7)	B1—H1	1.000
C131—H2	0.990
N11—Tl1—N21	74.36 (10)	C136—C137—H13	109.676
N11—Tl1—N31	78.17 (10)	C138—C137—H12	109.675
N21—Tl1—N31	76.78 (11)	C138—C137—H13	109.675
Tl1—N11—N12	119.2 (2)	H12—C137—H13	108.173
Tl1—N11—C140	130.6 (3)	C133—C138—H14	109.870
N12—N11—C140	107.3 (3)	C137—C138—H14	109.868
N11—N12—C160	109.4 (3)	C139—C138—H14	109.857
N11—N12—B1	123.0 (3)	C134—C139—H15	109.746
C160—N12—B1	127.6 (3)	C134—C139—H16	109.744
Tl1—N21—N22	121.3 (3)	C138—C139—H15	109.755
Tl1—N21—C240	131.3 (3)	C138—C139—H16	109.753
N22—N21—C240	107.4 (3)	H15—C139—H16	108.226
N21—N22—C260	109.6 (4)	C140—C150—H17	126.975
N21—N22—B1	120.5 (3)	C160—C150—H17	126.964
C260—N22—B1	129.8 (3)	C160—C170—H18	108.077
Tl1—N31—N32	120.4 (2)	C180—C170—H18	108.076
Tl1—N31—C340	131.2 (3)	C190—C170—H18	108.074
N32—N31—C340	107.0 (3)	C170—C180—H19	109.474
N31—N32—C360	109.7 (3)	C170—C180—H20	109.468
N31—N32—B1	121.3 (3)	C170—C180—H21	109.466
C360—N32—B1	129.0 (3)	H19—C180—H20	109.471
C131—C130—C132	109.7 (3)	H19—C180—H21	109.478
C131—C130—C133	108.4 (3)	H20—C180—H21	109.469
C131—C130—C140	111.9 (4)	C170—C190—H22	109.475
C132—C130—C133	108.0 (4)	C170—C190—H23	109.466
C132—C130—C140	109.4 (3)	C170—C190—H24	109.473
C133—C130—C140	109.3 (3)	H22—C190—H23	109.469
C130—C131—C134	110.1 (4)	H22—C190—H24	109.476
C130—C132—C136	110.1 (4)	H23—C190—H24	109.468
C130—C133—C138	111.1 (4)	C230—C231—H25	109.498
C131—C134—C135	110.2 (4)	C230—C231—H26	109.496
C131—C134—C139	108.9 (4)	C234—C231—H25	109.503
C135—C134—C139	109.2 (5)	C234—C231—H26	109.499
C134—C135—C136	109.6 (4)	H25—C231—H26	108.073
C132—C136—C135	109.4 (4)	C230—C232—H27	109.543
C132—C136—C137	109.6 (4)	C230—C232—H28	109.547
C135—C136—C137	109.3 (4)	C236—C232—H27	109.546
C136—C137—C138	109.9 (4)	C236—C232—H28	109.547
C133—C138—C137	108.7 (4)	H27—C232—H28	108.117
C133—C138—C139	109.2 (5)	C230—C233—H29	109.608
C137—C138—C139	109.4 (4)	C230—C233—H30	109.606
C134—C139—C138	109.6 (4)	C238—C233—H29	109.606
N11—C140—C130	122.1 (3)	C238—C233—H30	109.609
N11—C140—C150	109.6 (3)	H29—C233—H30	108.131
C130—C140—C150	128.3 (3)	C231—C234—H31	109.626
C140—C150—C160	106.1 (3)	C235—C234—H31	109.635
N12—C160—C150	107.7 (3)	C239—C234—H31	109.630
N12—C160—C170	124.1 (3)	C234—C235—H32	109.674
C150—C160—C170	128.2 (4)	C234—C235—H33	109.682
C160—C170—C180	109.9 (3)	C236—C235—H32	109.687
C160—C170—C190	110.9 (3)	C236—C235—H33	109.697
C180—C170—C190	111.7 (4)	H32—C235—H33	108.179
C231—C230—C232	109.7 (4)	C232—C236—H34	109.817
C231—C230—C233	108.0 (4)	C235—C236—H34	109.831
C231—C230—C240	111.1 (4)	C237—C236—H34	109.834
C232—C230—C233	107.6 (4)	C236—C237—H35	109.547
C232—C230—C240	109.8 (4)	C236—C237—H36	109.536
C233—C230—C240	110.5 (4)	C238—C237—H35	109.542
C230—C231—C234	110.7 (4)	C238—C237—H36	109.533
C230—C232—C236	110.5 (4)	H35—C237—H36	108.089
C230—C233—C238	110.2 (4)	C233—C238—H37	109.473
C231—C234—C235	109.8 (4)	C237—C238—H37	109.472
C231—C234—C239	108.4 (4)	C239—C238—H37	109.480
C235—C234—C239	109.7 (4)	C234—C239—H38	109.805
C234—C235—C236	109.9 (4)	C234—C239—H39	109.807
C232—C236—C235	109.1 (4)	C238—C239—H38	109.792
C232—C236—C237	108.4 (4)	C238—C239—H39	109.800
C235—C236—C237	109.8 (4)	H38—C239—H39	108.255
C236—C237—C238	110.6 (4)	C240—C250—H40	126.748
C233—C238—C237	109.6 (5)	C260—C250—H40	126.743
C233—C238—C239	109.4 (4)	C260—C270—H41	107.791
C237—C238—C239	109.4 (4)	C280—C270—H41	107.793
C234—C239—C238	109.4 (4)	C290—C270—H41	107.798
N21—C240—C230	121.1 (4)	C270—C280—H42	109.465
N21—C240—C250	109.2 (4)	C270—C280—H43	109.469
C230—C240—C250	129.7 (4)	C270—C280—H44	109.470
C240—C250—C260	106.5 (4)	H42—C280—H43	109.478
N22—C260—C250	107.3 (4)	H42—C280—H44	109.470
N22—C260—C270	124.4 (4)	H43—C280—H44	109.476
C250—C260—C270	128.3 (4)	C270—C290—H45	109.479
C260—C270—C280	112.8 (4)	C270—C290—H46	109.471
C260—C270—C290	110.7 (4)	C270—C290—H47	109.469
C280—C270—C290	109.8 (5)	H45—C290—H46	109.467
C331—C330—C332	109.0 (3)	H45—C290—H47	109.477
C331—C330—C333	107.5 (3)	H46—C290—H47	109.466
C331—C330—C340	110.6 (4)	C330—C331—H48	109.593
C332—C330—C333	107.8 (4)	C330—C331—H49	109.589
C332—C330—C340	111.5 (3)	C334—C331—H48	109.583
C333—C330—C340	110.4 (3)	C334—C331—H49	109.586
C330—C331—C334	110.3 (4)	H48—C331—H49	108.122
C330—C332—C336	111.5 (3)	C330—C332—H50	109.335
C330—C333—C338	110.4 (3)	C330—C332—H51	109.316
C331—C334—C335	109.9 (4)	C336—C332—H50	109.331
C331—C334—C339	109.0 (3)	C336—C332—H51	109.319
C335—C334—C339	109.7 (4)	H50—C332—H51	107.973
C334—C335—C336	110.1 (4)	C330—C333—H52	109.566
C332—C336—C335	109.7 (4)	C330—C333—H53	109.560
C332—C336—C337	109.0 (4)	C338—C333—H52	109.556
C335—C336—C337	108.6 (4)	C338—C333—H53	109.560
C336—C337—C338	109.4 (5)	H52—C333—H53	108.114
C333—C338—C337	110.4 (4)	C331—C334—H54	109.383
C333—C338—C339	109.0 (4)	C335—C334—H54	109.382
C337—C338—C339	109.7 (4)	C339—C334—H54	109.368
C334—C339—C338	109.0 (4)	C334—C335—H55	109.641
N31—C340—C330	121.4 (3)	C334—C335—H56	109.635
N31—C340—C350	110.2 (3)	C336—C335—H55	109.647
C330—C340—C350	128.4 (4)	C336—C335—H56	109.651
C340—C350—C360	105.8 (3)	H55—C335—H56	108.160
N32—C360—C350	107.4 (3)	C332—C336—H57	109.812
N32—C360—C370	124.8 (3)	C335—C336—H57	109.810
C350—C360—C370	127.6 (3)	C337—C336—H57	109.830
C360—C370—C380	109.2 (4)	C336—C337—H58	109.781
C360—C370—C390	111.4 (4)	C336—C337—H59	109.791
C380—C370—C390	110.9 (4)	C338—C337—H58	109.783
N12—B1—N22	111.6 (3)	C338—C337—H59	109.791
N12—B1—N32	110.8 (3)	H58—C337—H59	108.232
N22—B1—N32	109.5 (3)	C333—C338—H60	109.224
C130—C131—H2	109.649	C337—C338—H60	109.216
C130—C131—H3	109.662	C339—C338—H60	109.227
C134—C131—H2	109.643	C334—C339—H61	109.869
C134—C131—H3	109.645	C334—C339—H62	109.872
H2—C131—H3	108.156	C338—C339—H61	109.880
C130—C132—H4	109.642	C338—C339—H62	109.882
C130—C132—H5	109.643	H61—C339—H62	108.291
C136—C132—H4	109.634	C340—C350—H63	127.095
C136—C132—H5	109.635	C360—C350—H63	127.095
H4—C132—H5	108.154	C360—C370—H64	108.439
C130—C133—H6	109.409	C380—C370—H64	108.444
C130—C133—H7	109.419	C390—C370—H64	108.420
C138—C133—H6	109.406	C370—C380—H65	109.460
C138—C133—H7	109.406	C370—C380—H66	109.478
H6—C133—H7	108.022	C370—C380—H67	109.476
C131—C134—H8	109.507	H65—C380—H66	109.470
C135—C134—H8	109.505	H65—C380—H67	109.468
C139—C134—H8	109.500	H66—C380—H67	109.477
C134—C135—H9	109.747	C370—C390—H68	109.465
C134—C135—H10	109.750	C370—C390—H69	109.478
C136—C135—H9	109.759	C370—C390—H70	109.478
C136—C135—H10	109.751	H68—C390—H69	109.467
H9—C135—H10	108.213	H68—C390—H70	109.460
C132—C136—H11	109.500	H69—C390—H70	109.479
C135—C136—H11	109.502	N12—B1—H1	108.239
C137—C136—H11	109.499	N22—B1—H1	108.253
C136—C137—H12	109.674	N32—B1—H1	108.239
N11—Tl1—N21—N22	41.75 (18)	C137—C138—C139—C134	−59.7 (5)
N11—Tl1—N21—C240	−140.7 (3)	N11—C140—C150—C160	−0.6 (4)
N21—Tl1—N11—N12	−50.1 (2)	C130—C140—C150—C160	178.2 (4)
N21—Tl1—N11—C140	151.6 (3)	C140—C150—C160—N12	0.6 (4)
N11—Tl1—N31—N32	−42.6 (2)	C140—C150—C160—C170	−178.4 (4)
N11—Tl1—N31—C340	152.8 (3)	N12—C160—C170—C180	−82.3 (5)
N31—Tl1—N11—N12	29.3 (2)	N12—C160—C170—C190	153.7 (4)
N31—Tl1—N11—C140	−129.0 (3)	C150—C160—C170—C180	96.7 (5)
N21—Tl1—N31—N32	33.9 (2)	C150—C160—C170—C190	−27.3 (6)
N21—Tl1—N31—C340	−130.7 (3)	C231—C230—C232—C236	57.2 (5)
N31—Tl1—N21—N22	−39.46 (19)	C232—C230—C231—C234	−56.8 (5)
N31—Tl1—N21—C240	138.1 (3)	C231—C230—C233—C238	−59.2 (4)
Tl1—N11—N12—C160	−162.79 (17)	C233—C230—C231—C234	60.3 (4)
Tl1—N11—N12—B1	16.2 (4)	C231—C230—C240—N21	59.7 (5)
Tl1—N11—C140—C130	−18.4 (5)	C231—C230—C240—C250	−121.8 (4)
Tl1—N11—C140—C150	160.5 (2)	C240—C230—C231—C234	−178.3 (3)
N12—N11—C140—C130	−178.6 (3)	C232—C230—C233—C238	59.2 (4)
N12—N11—C140—C150	0.3 (4)	C233—C230—C232—C236	−60.2 (4)
C140—N11—N12—C160	0.1 (4)	C232—C230—C240—N21	−61.8 (4)
C140—N11—N12—B1	179.1 (3)	C232—C230—C240—C250	116.7 (4)
N11—N12—C160—C150	−0.5 (4)	C240—C230—C232—C236	179.5 (3)
N11—N12—C160—C170	178.7 (3)	C233—C230—C240—N21	179.6 (3)
N11—N12—B1—N22	50.9 (4)	C233—C230—C240—C250	−1.9 (5)
N11—N12—B1—N32	−71.5 (4)	C240—C230—C233—C238	179.1 (3)
C160—N12—B1—N22	−130.3 (4)	C230—C231—C234—C235	58.7 (5)
C160—N12—B1—N32	107.3 (4)	C230—C231—C234—C239	−61.2 (4)
B1—N12—C160—C150	−179.4 (3)	C230—C232—C236—C235	−59.0 (5)
B1—N12—C160—C170	−0.3 (6)	C230—C232—C236—C237	60.6 (4)
Tl1—N21—N22—C260	177.31 (14)	C230—C233—C238—C237	−59.8 (4)
Tl1—N21—N22—B1	1.2 (4)	C230—C233—C238—C239	60.1 (5)
Tl1—N21—C240—C230	0.4 (5)	C231—C234—C235—C236	−60.4 (5)
Tl1—N21—C240—C250	−178.38 (17)	C231—C234—C239—C238	60.4 (5)
N22—N21—C240—C230	178.2 (3)	C235—C234—C239—C238	−59.5 (5)
N22—N21—C240—C250	−0.6 (4)	C239—C234—C235—C236	58.7 (5)
C240—N21—N22—C260	−0.8 (4)	C234—C235—C236—C232	60.5 (5)
C240—N21—N22—B1	−176.8 (3)	C234—C235—C236—C237	−58.1 (5)
N21—N22—C260—C250	1.8 (4)	C232—C236—C237—C238	−60.1 (5)
N21—N22—C260—C270	−179.4 (3)	C235—C236—C237—C238	59.1 (5)
N21—N22—B1—N12	−60.6 (4)	C236—C237—C238—C233	60.0 (5)
N21—N22—B1—N32	62.6 (4)	C236—C237—C238—C239	−60.0 (5)
C260—N22—B1—N12	124.2 (4)	C233—C238—C239—C234	−60.2 (5)
C260—N22—B1—N32	−112.6 (4)	C237—C238—C239—C234	59.9 (6)
B1—N22—C260—C250	177.4 (3)	N21—C240—C250—C260	1.7 (4)
B1—N22—C260—C270	−3.8 (5)	C230—C240—C250—C260	−177.0 (3)
Tl1—N31—N32—C360	−167.99 (17)	C240—C250—C260—N22	−2.1 (4)
Tl1—N31—N32—B1	9.4 (4)	C240—C250—C260—C270	179.1 (3)
Tl1—N31—C340—C330	−12.3 (6)	N22—C260—C270—C280	−89.7 (4)
Tl1—N31—C340—C350	166.9 (2)	N22—C260—C270—C290	146.8 (3)
N32—N31—C340—C330	−178.5 (3)	C250—C260—C270—C280	88.9 (5)
N32—N31—C340—C350	0.7 (5)	C250—C260—C270—C290	−34.6 (5)
C340—N31—N32—C360	−0.0 (4)	C331—C330—C332—C336	57.2 (4)
C340—N31—N32—B1	177.3 (3)	C332—C330—C331—C334	−57.0 (4)
N31—N32—C360—C350	−0.7 (4)	C331—C330—C333—C338	−59.7 (4)
N31—N32—C360—C370	174.8 (3)	C333—C330—C331—C334	59.6 (4)
N31—N32—B1—N12	54.0 (5)	C331—C330—C340—N31	67.5 (5)
N31—N32—B1—N22	−69.7 (4)	C331—C330—C340—C350	−111.6 (4)
C360—N32—B1—N12	−129.3 (4)	C340—C330—C331—C334	−179.9 (3)
C360—N32—B1—N22	107.1 (4)	C332—C330—C333—C338	57.7 (4)
B1—N32—C360—C350	−177.7 (3)	C333—C330—C332—C336	−59.1 (4)
B1—N32—C360—C370	−2.3 (6)	C332—C330—C340—N31	−53.9 (5)
C131—C130—C132—C136	−58.7 (4)	C332—C330—C340—C350	127.0 (4)
C132—C130—C131—C134	57.7 (4)	C340—C330—C332—C336	179.5 (3)
C131—C130—C133—C138	59.1 (4)	C333—C330—C340—N31	−173.7 (4)
C133—C130—C131—C134	−60.0 (4)	C333—C330—C340—C350	7.2 (6)
C131—C130—C140—N11	−47.4 (5)	C340—C330—C333—C338	179.6 (3)
C131—C130—C140—C150	133.9 (4)	C330—C331—C334—C335	59.1 (4)
C140—C130—C131—C134	179.4 (3)	C330—C331—C334—C339	−61.2 (4)
C132—C130—C133—C138	−59.7 (4)	C330—C332—C336—C335	−58.4 (4)
C133—C130—C132—C136	59.3 (4)	C330—C332—C336—C337	60.5 (5)
C132—C130—C140—N11	74.4 (5)	C330—C333—C338—C337	−59.4 (5)
C132—C130—C140—C150	−104.2 (4)	C330—C333—C338—C339	61.2 (4)
C140—C130—C132—C136	178.2 (3)	C331—C334—C335—C336	−59.7 (4)
C133—C130—C140—N11	−167.5 (4)	C331—C334—C339—C338	61.1 (5)
C133—C130—C140—C150	13.8 (5)	C335—C334—C339—C338	−59.4 (4)
C140—C130—C133—C138	−178.6 (3)	C339—C334—C335—C336	60.2 (4)
C130—C131—C134—C135	−58.6 (5)	C334—C335—C336—C332	59.1 (4)
C130—C131—C134—C139	61.1 (4)	C334—C335—C336—C337	−60.0 (4)
C130—C132—C136—C135	59.7 (4)	C332—C336—C337—C338	−59.4 (5)
C130—C132—C136—C137	−60.2 (5)	C335—C336—C337—C338	60.2 (4)
C130—C133—C138—C137	60.0 (5)	C336—C337—C338—C333	59.4 (5)
C130—C133—C138—C139	−59.2 (5)	C336—C337—C338—C339	−60.7 (5)
C131—C134—C135—C136	59.6 (5)	C333—C338—C339—C334	−61.1 (4)
C131—C134—C139—C138	−60.4 (6)	C337—C338—C339—C334	60.0 (5)
C135—C134—C139—C138	60.0 (5)	N31—C340—C350—C360	−1.1 (5)
C139—C134—C135—C136	−60.0 (5)	C330—C340—C350—C360	178.0 (4)
C134—C135—C136—C132	−60.0 (5)	C340—C350—C360—N32	1.1 (5)
C134—C135—C136—C137	60.0 (5)	C340—C350—C360—C370	−174.2 (4)
C132—C136—C137—C138	60.0 (5)	N32—C360—C370—C380	−89.8 (4)
C135—C136—C137—C138	−59.9 (5)	N32—C360—C370—C390	147.4 (4)
C136—C137—C138—C133	−59.2 (5)	C350—C360—C370—C380	84.8 (5)
C136—C137—C138—C139	59.9 (5)	C350—C360—C370—C390	−38.0 (6)
C133—C138—C139—C134	59.1 (5)