2,7,10,13-Tetra-tert-butyl-N-phenyl­ace­naphtho[1,2-j]fluoranthene-4,5-dicarboximide

Ozoe, H.; Kitamura, C.; Nishida, J.; Kawase, T.

doi:10.1107/S2414314616004739

organic compounds

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ISSN: 2414-3146

Volume 1| Part 3| March 2016| x160473

doi:10.1107/S2414314616004739

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2,7,10,13-Tetra-tert-butyl-N-phenylacenaphtho[1,2-j]fluoranthene-4,5-dicarboximide

Hiroaki Ozoe,^a Chitoshi Kitamura,^b ^* Jun-ichi Nishida ^a and Takeshi Kawase ^a

^aDepartment of Applied Chemistry, Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan, and ^bDepartment of Materials Science, School of Engineering, The University of Shiga Prefecture, 2500 Hassaka-cho, Hikone, Shiga 522-8533, Japan
^*Correspondence e-mail: kitamura.c@mat.usp.ac.jp

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 19 March 2016; accepted 20 March 2016; online 31 March 2016)

In the molecule of the title compound, C₅₀H₄₉NO₂, the acenaphtho[1,2-j]fluoranthene-4,5-dicarboximide framework has an approximately planar structure [maximum deviation = 0.124 (3) Å] and subtends a dihedral angle of 62.94 (8)° with the pendant phenyl group. Two of the tert-butyl groups are disordered over two sets of sites, with occupancy ratios of 0.506 (8):0.494 (8) and 0.669 (17):0.331 (17). An intermolecular short contact between a methyl group and the aromatic ring occurs in the crystal structure.

Keywords: crystal structure; imide; tert-butyl group; disorder.

CCDC reference: 1469635

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Chemical scheme

Structure description

Imides having a polycyclic aromatic hydrocarbon skeleton are of interest as electronic devices. For example, naphthalenedimide and perylenedimide have been investigated (Weil et al., 2010 ). Very recently, we reported a new imide preparation by the Diels–Alder reaction of diacenaphtho[1,2-j]thiophene (Watson et al., 2000 ) and maleic anhydride, followed by treatment with amines to afford acenaphtho[1,2-j]fluoranthene-4,5-dicarboximide derivatives (Ozoe et al., 2014 ). To improve the solubility, the introduction of four tert-butyl groups onto the above ring was carried out. As a part of our ongoing research on the imide derivatives, we represent here the crystal structure of the title compound.

In the molecular structure of the title compound (Fig. 1), the acenaphtho[1,2-j]fluoranthene-4,5-dicarboximide framework has a nearly planar structure with a maximum deviation of 0.124 (3) Å for C12. The dihedral angle between the imide ring and the peripheral phenyl ring is 62.94 (8)°.

Figure 1
The molecular structure of the title compound, showing the atom-numbering with 50% probability displacement ellipsoids. Only the major occupancy disorder components are shown for clarity.

In the crystal (Fig. 2), the molecules adopt a herringbone-like arrangement without π–π stacking due to the steric hindrance of tert-butyl groups. There are no classical hydrogen bonds although there are intermolecular short contacts between C21 and H45Bⁱ of 2.87 (3) Å [symmetry code: (i) 1 – x, – $[{1\over 2}]$ + y, $[{3\over 2}]$ − z].

Figure 2
The crystal packing of the title compound. Only the major occupancy disorder components are shown for clarity. Intermolecular short contacts are drawn as blue lines.

Synthesis and crystallization

The Diels–Alder reaction of 2,5,9,12-tetra(tert-butyl)diacenaphtho[1,2-b:1′,2′-d]thiophene (Watson et al., 2000) and maleic anhydride at 225°C for 30 min under neat conditions provided an anhydride, which was then heated with aniline at reflux in dimethylformamide for 12 h (Fig. 3). After cooling, the title compound was obtained as stable yellow crystals in 55% yield over the two steps. ¹H -NMR (CDCl₃, 500 MHz) δ 9.57 (s, 2H),9.05 (s, 2H), 8.05 (s, 2H), 8.01 (s, 2H), 7.63–7.62 (m, 4H), 7.52–7.49 (m,1H), 1.68 (s, 18H), 1.57 (s, 18H). MS (EI) m/z 695 (M⁺,100), 680 (12), 333 (75).

Figure 3
Reaction scheme for the synthesis of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. Two tert-butyl groups are each disordered over two sets of sites; the site occupancy factors are 0.506 (8) for C44A–C46A and 0.494 (8) for C44B–C46B, and 0.669 (17) for C48A–C50A and 0.331 (17) for C48B–C50B.

Table 1
Experimental details

Crystal data
Chemical formula	C₅₀H₄₉NO₂
M_r	695.9
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	19.155 (3), 10.5762 (14), 19.495 (3)
β (°)	92.382 (3)
V (Å³)	3946.0 (10)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.50 × 0.45 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID
No. of measured, independent and observed [I > 2σ(I)] reflections	36876, 9011, 4306
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.243, 1.06
No. of reflections	9011
No. of parameters	534
No. of restraints	60
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.25
Computer programs: PROCESS-AUTO (Rigaku, 1998 ), SIR2004 (Burla et al., 2005 ), SHELXL2014 (Sheldrick, 2015 ), Mercury (Macrae et al., 2008 ), WinGX (Farrugia, 2012 ).

Structural data

CCDC reference: 1469635

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616004739/hb4031sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616004739/hb4031Isup2.hkl

checkCIF report

Experimental top

The Diels–Alder reaction of 2,5,9,12-tetra(tert-butyl)diacenaphtho[1,2 − b:1',2'-d]thiophene (Watson et al., 2000) and maleic anhydride at 225°C for 30 min under neat conditions provided an anhydride, which was then heated with aniline at reflux in dimethylformamide for 12 h. After cooling, the title compound was obtained as stable yellow crystals in 55% yield over the two steps. ¹H –NMR (CDCl₃, 500 MHz) δ 9.57 (s, 2H),9.05 (s, 2H), 8.05 (s, 2H), 8.01 (s, 2H), 7.63–7.62 (m, 4H), 7.52–7.49 (m,1H), 1.68 (s, 18H), 1.57 (s, 18H). MS (EI) m/z 695 (M⁺,100), 680 (12), 333 (75).

Structure description top

Imides having a polycyclic aromatic hydrocarbon skeleton are of interest as electronic devices. For example, naphthalenedimide and perylenedimide have been investigated (Weil et al., 2010). Very recently, we reported a new imide preparation by the Diels–Alder reaction of diacenaphtho[1,2 − b:1',2'-d]thiophene (Watson et al., 2000) and maleic anhydride, followed by treatment with amines to afford acenaphtho[1,2 − b:1',2'-d]fluoranthene-4,5-dicarboximide derivatives (Ozoe et al., 2014). To improve the solubility, the introduction of four tert-butyl groups onto the above ring was carried out. As a part of our ongoing research on the imide derivatives, we represent here the crystal structure of the title compound.

In the molecular structure of the title compound (Fig. 1), the acenaphtho[1,2 − b:1',2'-d]fluoranthene-4,5-dicarboximide framework has a nearly planar structure with a maximum deviation of 0.124 (3) Å for C12. The dihedral angle between the imide ring and the peripheral phenyl ring is 62.94 (8)°.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: PROCESS-AUTO (Rigaku, 1998); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom-numbering with 50% probability displacement ellipsoids. Only the major occupancy disorder components are shown for clarity.
	Fig. 2. The crystal packing of the title compound. Only the major occupancy disorder components are shown for clarity. Intermolecular short contacts are drawn as blue lines.
	Fig. 3. Reaction scheme for the synthesis of the title compound.

2,7,10,13-Tetra-tert-butyl-N-phenylacenaphtho[1,2-j]fluoranthene-4,5-dicarboximide top

Crystal data top

C₅₀H₄₉NO₂	F(000) = 1488
M_r = 695.9	D_x = 1.171 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10293 reflections
a = 19.155 (3) Å	θ = 3–27.4°
b = 10.5762 (14) Å	µ = 0.07 mm⁻¹
c = 19.495 (3) Å	T = 223 K
β = 92.382 (3)°	Prism, yellow
V = 3946.0 (10) Å³	0.50 × 0.45 × 0.18 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4306 reflections with I > 2σ(I)
Radiation source: fine-focus sealed x-ray tube	R_int = 0.082
Graphite monochromator	θ_max = 27.5°, θ_min = 3.0°
Detector resolution: 10 pixels mm^-1	h = −24→24
φ and ω scans	k = −13→13
36876 measured reflections	l = −25→25
9011 independent reflections

Refinement top

Refinement on F²	60 restraints
Least-squares matrix: full	0 constraints
R[F² > 2σ(F²)] = 0.077	H-atom parameters constrained
wR(F²) = 0.243	w = 1/[σ²(F_o²) + (0.0978P)² + 1.0477P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max = 0.001
9011 reflections	Δρ_max = 0.34 e Å⁻³
534 parameters	Δρ_min = −0.25 e Å⁻³

Crystal data top

C₅₀H₄₉NO₂	V = 3946.0 (10) Å³
M_r = 695.9	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 19.155 (3) Å	µ = 0.07 mm⁻¹
b = 10.5762 (14) Å	T = 223 K
c = 19.495 (3) Å	0.50 × 0.45 × 0.18 mm
β = 92.382 (3)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4306 reflections with I > 2σ(I)
36876 measured reflections	R_int = 0.082
9011 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	60 restraints
wR(F²) = 0.243	H-atom parameters constrained
S = 1.06	Δρ_max = 0.34 e Å⁻³
9011 reflections	Δρ_min = −0.25 e Å⁻³
534 parameters

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. To refine the structure, the SHELX commands, such as DELU and SADI, were used because two tert-butyl groups were disordered over two positions. All the H atoms were positioned geometrically and refined using a riding model.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.13806 (16)	0.0838 (3)	0.80828 (15)	0.0526 (7)
C2	0.18062 (15)	0.2011 (2)	0.80595 (14)	0.0494 (7)
C3	0.18331 (14)	0.3038 (3)	0.84956 (14)	0.0509 (7)
C4	0.15047 (15)	0.3296 (3)	0.91487 (14)	0.0518 (7)
C5	0.10657 (16)	0.2646 (3)	0.95600 (15)	0.0551 (7)
H5	0.0911	0.1833	0.9431	0.066*
C6	0.08416 (16)	0.3193 (3)	1.01825 (15)	0.0565 (8)
C7	0.10950 (16)	0.4367 (3)	1.03773 (15)	0.0601 (8)
H7	0.0955	0.4721	1.0792	0.072*
C8	0.15568 (16)	0.5050 (3)	0.99720 (14)	0.0547 (7)
C9	0.17466 (15)	0.4498 (3)	0.93602 (14)	0.0522 (7)
C10	0.18541 (16)	0.6257 (3)	1.01245 (15)	0.0583 (8)
H10	0.1753	0.6662	1.0538	0.07*
C11	0.22873 (16)	0.6841 (3)	0.96766 (15)	0.0548 (7)
C12	0.24549 (16)	0.6228 (3)	0.90557 (15)	0.0558 (7)
H12	0.2747	0.6639	0.8751	0.067*
C13	0.21992 (15)	0.5050 (3)	0.88923 (14)	0.0516 (7)
C14	0.22796 (15)	0.4107 (3)	0.83327 (14)	0.0501 (7)
C15	0.26736 (14)	0.4054 (3)	0.77527 (14)	0.0497 (7)
C16	0.31842 (14)	0.4932 (3)	0.74463 (14)	0.0508 (7)
C17	0.34844 (16)	0.6078 (3)	0.76063 (15)	0.0581 (8)
H17	0.3354	0.6501	0.8005	0.07*
C18	0.39867 (16)	0.6642 (3)	0.71856 (15)	0.0590 (8)
C19	0.41857 (15)	0.6022 (3)	0.66032 (15)	0.0580 (8)
H19	0.4518	0.6397	0.6326	0.07*
C20	0.39002 (15)	0.4833 (3)	0.64136 (14)	0.0535 (7)
C21	0.34122 (15)	0.4334 (3)	0.68469 (14)	0.0514 (7)
C22	0.40672 (16)	0.4094 (3)	0.58431 (15)	0.0592 (8)
H22	0.4395	0.4405	0.554	0.071*
C23	0.37641 (16)	0.2922 (3)	0.57127 (15)	0.0570 (8)
C24	0.32698 (16)	0.2448 (3)	0.61681 (15)	0.0579 (8)
H24	0.3059	0.1657	0.6084	0.07*
C25	0.30968 (15)	0.3147 (3)	0.67363 (15)	0.0522 (7)
C26	0.26357 (15)	0.2958 (3)	0.73085 (14)	0.0519 (7)
C27	0.22046 (15)	0.1962 (3)	0.74767 (14)	0.0527 (7)
C28	0.20711 (16)	0.0730 (3)	0.71275 (15)	0.0564 (7)
C29	0.12609 (16)	−0.1075 (3)	0.73321 (15)	0.0538 (7)
C30	0.05538 (17)	−0.1131 (3)	0.71880 (16)	0.0650 (9)
H30	0.0279	−0.0399	0.7222	0.078*
C31	0.0247 (2)	−0.2257 (4)	0.69935 (18)	0.0770 (10)
H31	−0.0237	−0.2296	0.6897	0.092*
C32	0.0646 (2)	−0.3319 (3)	0.69411 (19)	0.0815 (11)
H32	0.0436	−0.4087	0.6805	0.098*
C33	0.1350 (2)	−0.3271 (3)	0.70859 (19)	0.0814 (11)
H33	0.1621	−0.4008	0.7053	0.098*
C34	0.16656 (19)	−0.2143 (3)	0.72803 (18)	0.0713 (9)
H34	0.215	−0.2107	0.7376	0.086*
C35	0.03577 (18)	0.2437 (3)	1.06289 (16)	0.0660 (9)
C36	0.0768 (3)	0.1391 (5)	1.0968 (3)	0.142 (2)
H36A	0.0988	0.0888	1.0621	0.213*
H36B	0.1125	0.1746	1.1279	0.213*
H36C	0.0459	0.086	1.1223	0.213*
C37	−0.0240 (2)	0.1860 (5)	1.0184 (2)	0.1108 (15)
H37A	−0.051	0.2532	0.9962	0.166*
H37B	−0.0049	0.1317	0.9838	0.166*
H37C	−0.054	0.1368	1.0471	0.166*
C38	0.0006 (3)	0.3247 (4)	1.1149 (2)	0.1224 (18)
H38A	−0.0256	0.3915	1.0914	0.184*
H38B	−0.031	0.273	1.1406	0.184*
H38C	0.0356	0.3617	1.1461	0.184*
C39	0.26024 (16)	0.8157 (3)	0.98251 (16)	0.0593 (8)
C40	0.34018 (17)	0.8035 (3)	0.98656 (19)	0.0777 (10)
H40A	0.3559	0.7684	0.9439	0.117*
H40B	0.3609	0.8863	0.994	0.117*
H40C	0.3542	0.7481	1.0243	0.117*
C41	0.2368 (2)	0.8709 (3)	1.04987 (18)	0.0803 (11)
H41A	0.2512	0.8151	1.0874	0.121*
H41B	0.258	0.9534	1.0571	0.121*
H41C	0.1864	0.8792	1.0481	0.121*
C42	0.2369 (2)	0.9054 (3)	0.9243 (2)	0.0848 (11)
H42A	0.2514	0.8717	0.8809	0.127*
H42B	0.1864	0.9137	0.9231	0.127*
H42C	0.2581	0.9878	0.932	0.127*
C43	0.43054 (17)	0.7933 (3)	0.73791 (16)	0.0719 (10)
C44A	0.4078 (5)	0.8843 (6)	0.6781 (4)	0.097 (3)	0.506 (8)
H44A	0.4223	0.8495	0.6349	0.146*	0.506 (8)
H44B	0.3573	0.8938	0.6766	0.146*	0.506 (8)
H44C	0.4295	0.9663	0.6856	0.146*	0.506 (8)
C45A	0.5101 (3)	0.7829 (9)	0.7374 (5)	0.104 (4)	0.506 (8)
H45A	0.5234	0.7467	0.6942	0.156*	0.506 (8)
H45B	0.5306	0.8663	0.7429	0.156*	0.506 (8)
H45C	0.5266	0.729	0.7749	0.156*	0.506 (8)
C46A	0.4076 (5)	0.8490 (8)	0.8041 (4)	0.116 (5)	0.506 (8)
H46A	0.357	0.8545	0.803	0.175*	0.506 (8)
H46B	0.4235	0.7956	0.842	0.175*	0.506 (8)
H46C	0.4275	0.9329	0.81	0.175*	0.506 (8)
C44B	0.3721 (4)	0.8919 (7)	0.7425 (6)	0.117 (4)	0.494 (8)
H44D	0.3358	0.8593	0.771	0.175*	0.494 (8)
H44E	0.391	0.9691	0.7625	0.175*	0.494 (8)
H44F	0.3524	0.9094	0.6968	0.175*	0.494 (8)
C45B	0.4872 (4)	0.8431 (9)	0.6937 (4)	0.099 (4)	0.494 (8)
H45D	0.524	0.7805	0.691	0.148*	0.494 (8)
H45E	0.4677	0.8606	0.6479	0.148*	0.494 (8)
H45F	0.5064	0.9203	0.7137	0.148*	0.494 (8)
C46B	0.4629 (5)	0.7759 (10)	0.8120 (4)	0.120 (4)	0.494 (8)
H46D	0.4275	0.7439	0.8417	0.179*	0.494 (8)
H46E	0.5013	0.7164	0.8112	0.179*	0.494 (8)
H46F	0.4799	0.8567	0.8293	0.179*	0.494 (8)
C47	0.39577 (15)	0.2151 (3)	0.50786 (16)	0.0650 (9)
C48A	0.3656 (5)	0.2781 (9)	0.4436 (4)	0.098 (3)	0.669 (17)
H48A	0.3153	0.2853	0.4464	0.147*	0.669 (17)
H48B	0.3858	0.3617	0.4393	0.147*	0.669 (17)
H48C	0.3764	0.2277	0.4038	0.147*	0.669 (17)
C49A	0.3670 (4)	0.0805 (6)	0.5102 (4)	0.079 (3)	0.669 (17)
H49A	0.3857	0.0382	0.5511	0.119*	0.669 (17)
H49B	0.3165	0.0833	0.5111	0.119*	0.669 (17)
H49C	0.3807	0.0346	0.4698	0.119*	0.669 (17)
C50A	0.4745 (3)	0.2045 (9)	0.5027 (6)	0.095 (3)	0.669 (17)
H50A	0.4943	0.1642	0.5438	0.142*	0.669 (17)
H50B	0.485	0.1543	0.4629	0.142*	0.669 (17)
H50C	0.4944	0.2883	0.4983	0.142*	0.669 (17)
C48B	0.4588 (13)	0.275 (3)	0.4776 (14)	0.198 (18)	0.331 (17)
H48D	0.4492	0.363	0.4675	0.298*	0.331 (17)
H48E	0.4984	0.2686	0.5102	0.298*	0.331 (17)
H48F	0.4696	0.2309	0.4357	0.298*	0.331 (17)
C49B	0.3336 (12)	0.227 (3)	0.4581 (13)	0.168 (15)	0.331 (17)
H49D	0.3251	0.3157	0.448	0.252*	0.331 (17)
H49E	0.3429	0.1824	0.4161	0.252*	0.331 (17)
H49F	0.2927	0.191	0.4784	0.252*	0.331 (17)
C50B	0.409 (2)	0.0784 (12)	0.5240 (13)	0.218 (18)	0.331 (17)
H50D	0.3682	0.0414	0.5434	0.327*	0.331 (17)
H50E	0.4199	0.0338	0.4822	0.327*	0.331 (17)
H50F	0.4487	0.0715	0.5568	0.327*	0.331 (17)
N1	0.15753 (12)	0.0106 (2)	0.75189 (12)	0.0543 (6)
O1	0.09504 (10)	0.05126 (18)	0.84835 (10)	0.0586 (5)
O2	0.23169 (12)	0.0291 (2)	0.66200 (11)	0.0686 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0579 (18)	0.0469 (17)	0.0531 (17)	0.0005 (14)	0.0048 (15)	0.0011 (14)
C2	0.0566 (17)	0.0405 (15)	0.0513 (16)	−0.0050 (13)	0.0050 (13)	−0.0031 (13)
C3	0.0506 (16)	0.0475 (16)	0.0552 (16)	−0.0021 (13)	0.0076 (13)	0.0008 (14)
C4	0.0543 (17)	0.0509 (17)	0.0506 (16)	−0.0028 (14)	0.0074 (14)	−0.0036 (14)
C5	0.0603 (18)	0.0499 (17)	0.0556 (17)	−0.0053 (14)	0.0082 (14)	−0.0047 (14)
C6	0.0633 (19)	0.0526 (18)	0.0542 (17)	−0.0045 (15)	0.0114 (15)	−0.0010 (14)
C7	0.072 (2)	0.0584 (19)	0.0508 (16)	−0.0023 (16)	0.0136 (15)	−0.0039 (15)
C8	0.0625 (18)	0.0509 (17)	0.0515 (16)	−0.0003 (14)	0.0107 (14)	−0.0042 (14)
C9	0.0597 (18)	0.0464 (16)	0.0509 (16)	−0.0047 (14)	0.0061 (14)	−0.0044 (14)
C10	0.069 (2)	0.0533 (18)	0.0530 (17)	−0.0002 (15)	0.0070 (15)	−0.0070 (14)
C11	0.0584 (18)	0.0468 (17)	0.0594 (17)	−0.0019 (14)	0.0038 (15)	−0.0016 (14)
C12	0.0629 (19)	0.0491 (17)	0.0558 (17)	−0.0064 (14)	0.0086 (15)	−0.0025 (14)
C13	0.0566 (17)	0.0459 (16)	0.0527 (16)	−0.0023 (13)	0.0064 (14)	−0.0036 (14)
C14	0.0555 (17)	0.0455 (16)	0.0497 (15)	−0.0033 (13)	0.0062 (13)	−0.0007 (13)
C15	0.0515 (16)	0.0457 (16)	0.0519 (16)	−0.0063 (13)	0.0038 (13)	0.0014 (13)
C16	0.0494 (16)	0.0534 (17)	0.0499 (16)	−0.0026 (14)	0.0043 (13)	0.0013 (14)
C17	0.0596 (18)	0.0565 (18)	0.0585 (18)	−0.0089 (15)	0.0081 (15)	−0.0039 (15)
C18	0.0591 (18)	0.0581 (19)	0.0600 (18)	−0.0116 (15)	0.0068 (15)	0.0014 (15)
C19	0.0556 (18)	0.0594 (19)	0.0597 (18)	−0.0074 (15)	0.0100 (15)	0.0059 (16)
C20	0.0511 (17)	0.0572 (18)	0.0527 (16)	−0.0012 (14)	0.0090 (14)	0.0034 (14)
C21	0.0511 (16)	0.0528 (17)	0.0502 (16)	−0.0015 (14)	0.0016 (13)	0.0027 (14)
C22	0.0575 (18)	0.062 (2)	0.0588 (18)	0.0003 (15)	0.0123 (15)	0.0040 (16)
C23	0.0554 (18)	0.0608 (19)	0.0554 (17)	0.0001 (15)	0.0100 (14)	0.0014 (15)
C24	0.0634 (19)	0.0538 (18)	0.0571 (17)	−0.0024 (15)	0.0086 (15)	−0.0028 (15)
C25	0.0499 (16)	0.0509 (17)	0.0560 (17)	0.0000 (14)	0.0037 (13)	−0.0014 (14)
C26	0.0535 (17)	0.0506 (17)	0.0517 (16)	−0.0037 (14)	0.0049 (14)	−0.0026 (14)
C27	0.0594 (18)	0.0465 (17)	0.0525 (16)	−0.0033 (14)	0.0066 (14)	−0.0032 (14)
C28	0.0580 (18)	0.0539 (18)	0.0578 (18)	−0.0050 (15)	0.0070 (15)	−0.0027 (15)
C29	0.0619 (19)	0.0470 (17)	0.0531 (16)	−0.0067 (15)	0.0107 (14)	−0.0019 (14)
C30	0.063 (2)	0.059 (2)	0.073 (2)	−0.0064 (16)	0.0035 (17)	0.0001 (17)
C31	0.073 (2)	0.076 (2)	0.082 (2)	−0.023 (2)	0.0037 (19)	−0.010 (2)
C32	0.101 (3)	0.056 (2)	0.090 (3)	−0.024 (2)	0.020 (2)	−0.0182 (19)
C33	0.094 (3)	0.051 (2)	0.100 (3)	0.0001 (19)	0.015 (2)	−0.0119 (19)
C34	0.072 (2)	0.056 (2)	0.086 (2)	−0.0024 (17)	0.0043 (18)	−0.0076 (18)
C35	0.077 (2)	0.059 (2)	0.0634 (19)	−0.0109 (17)	0.0210 (17)	−0.0002 (16)
C36	0.133 (4)	0.131 (4)	0.164 (5)	0.007 (3)	0.042 (4)	0.087 (4)
C37	0.094 (3)	0.132 (4)	0.109 (3)	−0.041 (3)	0.040 (3)	−0.021 (3)
C38	0.164 (4)	0.095 (3)	0.115 (3)	−0.036 (3)	0.091 (3)	−0.021 (3)
C39	0.066 (2)	0.0483 (18)	0.0645 (18)	−0.0062 (15)	0.0067 (15)	−0.0082 (15)
C40	0.067 (2)	0.073 (2)	0.093 (3)	−0.0135 (18)	0.0037 (19)	−0.019 (2)
C41	0.087 (3)	0.063 (2)	0.092 (3)	−0.0127 (19)	0.016 (2)	−0.0286 (19)
C42	0.105 (3)	0.050 (2)	0.099 (3)	−0.0102 (19)	−0.006 (2)	0.0023 (19)
C43	0.076 (2)	0.069 (2)	0.071 (2)	−0.0269 (19)	0.0115 (18)	−0.0057 (18)
C44A	0.129 (9)	0.055 (4)	0.107 (7)	−0.021 (5)	0.011 (6)	0.006 (4)
C45A	0.077 (6)	0.115 (8)	0.120 (8)	−0.044 (5)	0.007 (5)	−0.029 (6)
C46A	0.172 (12)	0.081 (7)	0.101 (7)	−0.067 (8)	0.064 (8)	−0.038 (6)
C44B	0.129 (8)	0.058 (5)	0.164 (12)	−0.021 (5)	0.033 (8)	−0.021 (6)
C45B	0.108 (8)	0.096 (7)	0.093 (7)	−0.050 (6)	0.027 (6)	−0.011 (5)
C46B	0.149 (10)	0.117 (9)	0.092 (6)	−0.076 (8)	−0.002 (7)	−0.019 (6)
C47	0.065 (2)	0.069 (2)	0.0624 (19)	−0.0029 (17)	0.0161 (16)	−0.0084 (17)
C48A	0.132 (8)	0.101 (6)	0.061 (4)	0.025 (6)	0.004 (5)	−0.009 (4)
C49A	0.087 (5)	0.061 (4)	0.094 (4)	−0.009 (3)	0.044 (4)	−0.032 (3)
C50A	0.066 (4)	0.101 (6)	0.120 (6)	−0.005 (4)	0.028 (4)	−0.041 (5)
C48B	0.20 (3)	0.24 (3)	0.17 (3)	−0.11 (2)	0.14 (2)	−0.14 (2)
C49B	0.125 (18)	0.24 (3)	0.13 (2)	0.029 (18)	−0.053 (15)	−0.13 (2)
C50B	0.28 (4)	0.126 (17)	0.27 (3)	0.14 (2)	0.18 (3)	0.074 (18)
N1	0.0595 (15)	0.0456 (13)	0.0585 (14)	−0.0083 (12)	0.0116 (12)	−0.0074 (12)
O1	0.0627 (13)	0.0522 (12)	0.0620 (12)	−0.0076 (10)	0.0150 (11)	−0.0002 (10)
O2	0.0826 (15)	0.0606 (13)	0.0641 (13)	−0.0121 (11)	0.0223 (12)	−0.0127 (11)

Geometric parameters (Å, º) top

C1—O1	1.209 (3)	C36—H36C	0.97
C1—N1	1.407 (4)	C37—H37A	0.97
C1—C2	1.487 (4)	C37—H37B	0.97
C2—C3	1.379 (4)	C37—H37C	0.97
C2—C27	1.396 (4)	C38—H38A	0.97
C3—C14	1.461 (4)	C38—H38B	0.97
C3—C4	1.469 (4)	C38—H38C	0.97
C4—C5	1.371 (4)	C39—C41	1.521 (4)
C4—C9	1.409 (4)	C39—C42	1.532 (5)
C5—C6	1.426 (4)	C39—C40	1.535 (4)
C5—H5	0.94	C40—H40A	0.97
C6—C7	1.381 (4)	C40—H40B	0.97
C6—C35	1.524 (4)	C40—H40C	0.97
C7—C8	1.409 (4)	C41—H41A	0.97
C7—H7	0.94	C41—H41B	0.97
C8—C9	1.390 (4)	C41—H41C	0.97
C8—C10	1.425 (4)	C42—H42A	0.97
C9—C13	1.411 (4)	C42—H42B	0.97
C10—C11	1.376 (4)	C42—H42C	0.97
C10—H10	0.94	C43—C46A	1.501 (6)
C11—C12	1.422 (4)	C43—C45B	1.509 (6)
C11—C39	1.539 (4)	C43—C45A	1.527 (6)
C12—C13	1.371 (4)	C43—C44B	1.535 (6)
C12—H12	0.94	C43—C46B	1.559 (6)
C13—C14	1.491 (4)	C43—C44A	1.561 (6)
C14—C15	1.386 (4)	C44A—H44A	0.97
C15—C26	1.447 (4)	C44A—H44B	0.97
C15—C16	1.491 (4)	C44A—H44C	0.97
C16—C17	1.372 (4)	C45A—H45A	0.97
C16—C21	1.414 (4)	C45A—H45B	0.97
C17—C18	1.422 (4)	C45A—H45C	0.97
C17—H17	0.94	C46A—H46A	0.97
C18—C19	1.379 (4)	C46A—H46B	0.97
C18—C43	1.536 (4)	C46A—H46C	0.97
C19—C20	1.414 (4)	C44B—H44D	0.97
C19—H19	0.94	C44B—H44E	0.97
C20—C21	1.390 (4)	C44B—H44F	0.97
C20—C22	1.407 (4)	C45B—H45D	0.97
C21—C25	1.406 (4)	C45B—H45E	0.97
C22—C23	1.388 (4)	C45B—H45F	0.97
C22—H22	0.94	C46B—H46D	0.97
C23—C24	1.417 (4)	C46B—H46E	0.97
C23—C47	1.539 (4)	C46B—H46F	0.97
C24—C25	1.384 (4)	C47—C50B	1.501 (7)
C24—H24	0.94	C47—C48B	1.504 (7)
C25—C26	1.465 (4)	C47—C49B	1.510 (7)
C26—C27	1.386 (4)	C47—C48A	1.512 (6)
C27—C28	1.488 (4)	C47—C50A	1.519 (6)
C28—O2	1.206 (3)	C47—C49A	1.528 (5)
C28—N1	1.407 (4)	C48A—H48A	0.97
C29—C30	1.373 (4)	C48A—H48B	0.97
C29—C34	1.376 (4)	C48A—H48C	0.97
C29—N1	1.427 (4)	C49A—H49A	0.97
C30—C31	1.374 (4)	C49A—H49B	0.97
C30—H30	0.94	C49A—H49C	0.97
C31—C32	1.365 (5)	C50A—H50A	0.97
C31—H31	0.94	C50A—H50B	0.97
C32—C33	1.367 (5)	C50A—H50C	0.97
C32—H32	0.94	C48B—H48D	0.97
C33—C34	1.383 (5)	C48B—H48E	0.97
C33—H33	0.94	C48B—H48F	0.97
C34—H34	0.94	C49B—H49D	0.97
C35—C36	1.495 (5)	C49B—H49E	0.97
C35—C38	1.508 (5)	C49B—H49F	0.97
C35—C37	1.535 (5)	C50B—H50D	0.97
C36—H36A	0.97	C50B—H50E	0.97
C36—H36B	0.97	C50B—H50F	0.97

O1—C1—N1	123.9 (3)	H38B—C38—H38C	109.5
O1—C1—C2	130.3 (3)	C41—C39—C42	108.4 (3)
N1—C1—C2	105.8 (2)	C41—C39—C40	108.5 (3)
C3—C2—C27	121.6 (3)	C42—C39—C40	110.5 (3)
C3—C2—C1	130.2 (3)	C41—C39—C11	112.4 (3)
C27—C2—C1	108.2 (2)	C42—C39—C11	108.7 (2)
C2—C3—C14	118.9 (3)	C40—C39—C11	108.4 (3)
C2—C3—C4	132.4 (3)	C39—C40—H40A	109.5
C14—C3—C4	108.7 (2)	C39—C40—H40B	109.5
C5—C4—C9	118.9 (3)	H40A—C40—H40B	109.5
C5—C4—C3	135.2 (3)	C39—C40—H40C	109.5
C9—C4—C3	105.9 (2)	H40A—C40—H40C	109.5
C4—C5—C6	120.5 (3)	H40B—C40—H40C	109.5
C4—C5—H5	119.7	C39—C41—H41A	109.5
C6—C5—H5	119.7	C39—C41—H41B	109.5
C7—C6—C5	118.9 (3)	H41A—C41—H41B	109.5
C7—C6—C35	122.0 (3)	C39—C41—H41C	109.5
C5—C6—C35	119.0 (3)	H41A—C41—H41C	109.5
C6—C7—C8	121.9 (3)	H41B—C41—H41C	109.5
C6—C7—H7	119.1	C39—C42—H42A	109.5
C8—C7—H7	119.1	C39—C42—H42B	109.5
C9—C8—C7	117.3 (3)	H42A—C42—H42B	109.5
C9—C8—C10	116.0 (3)	C39—C42—H42C	109.5
C7—C8—C10	126.7 (3)	H42A—C42—H42C	109.5
C8—C9—C4	122.4 (3)	H42B—C42—H42C	109.5
C8—C9—C13	124.8 (3)	C46A—C43—C45A	111.2 (4)
C4—C9—C13	112.8 (2)	C45B—C43—C44B	109.9 (4)
C11—C10—C8	121.1 (3)	C46A—C43—C18	115.6 (4)
C11—C10—H10	119.5	C45B—C43—C18	117.3 (4)
C8—C10—H10	119.5	C45A—C43—C18	108.7 (4)
C10—C11—C12	119.9 (3)	C44B—C43—C18	109.5 (4)
C10—C11—C39	121.9 (3)	C45B—C43—C46B	107.7 (4)
C12—C11—C39	118.2 (3)	C44B—C43—C46B	106.8 (4)
C13—C12—C11	121.4 (3)	C18—C43—C46B	105.1 (4)
C13—C12—H12	119.3	C46A—C43—C44A	108.5 (4)
C11—C12—H12	119.3	C45A—C43—C44A	106.7 (4)
C12—C13—C9	116.7 (3)	C18—C43—C44A	105.6 (3)
C12—C13—C14	137.0 (3)	C43—C44A—H44A	109.5
C9—C13—C14	106.3 (2)	C43—C44A—H44B	109.5
C15—C14—C3	119.3 (2)	H44A—C44A—H44B	109.5
C15—C14—C13	134.4 (3)	C43—C44A—H44C	109.5
C3—C14—C13	106.2 (2)	H44A—C44A—H44C	109.5
C14—C15—C26	120.3 (2)	H44B—C44A—H44C	109.5
C14—C15—C16	133.6 (3)	C43—C45A—H45A	109.5
C26—C15—C16	106.0 (2)	C43—C45A—H45B	109.5
C17—C16—C21	116.2 (3)	H45A—C45A—H45B	109.5
C17—C16—C15	137.3 (3)	C43—C45A—H45C	109.5
C21—C16—C15	106.4 (2)	H45A—C45A—H45C	109.5
C16—C17—C18	121.8 (3)	H45B—C45A—H45C	109.5
C16—C17—H17	119.1	C43—C46A—H46A	109.5
C18—C17—H17	119.1	C43—C46A—H46B	109.5
C19—C18—C17	119.5 (3)	H46A—C46A—H46B	109.5
C19—C18—C43	120.3 (3)	C43—C46A—H46C	109.5
C17—C18—C43	120.2 (3)	H46A—C46A—H46C	109.5
C18—C19—C20	121.4 (3)	H46B—C46A—H46C	109.5
C18—C19—H19	119.3	C43—C44B—H44D	109.5
C20—C19—H19	119.3	C43—C44B—H44E	109.5
C21—C20—C22	116.7 (3)	H44D—C44B—H44E	109.5
C21—C20—C19	116.2 (3)	C43—C44B—H44F	109.5
C22—C20—C19	127.0 (3)	H44D—C44B—H44F	109.5
C20—C21—C25	122.8 (3)	H44E—C44B—H44F	109.5
C20—C21—C16	124.8 (3)	C43—C45B—H45D	109.5
C25—C21—C16	112.4 (3)	C43—C45B—H45E	109.5
C23—C22—C20	122.3 (3)	H45D—C45B—H45E	109.5
C23—C22—H22	118.9	C43—C45B—H45F	109.5
C20—C22—H22	118.9	H45D—C45B—H45F	109.5
C22—C23—C24	119.2 (3)	H45E—C45B—H45F	109.5
C22—C23—C47	120.5 (3)	C43—C46B—H46D	109.5
C24—C23—C47	120.3 (3)	C43—C46B—H46E	109.5
C25—C24—C23	120.0 (3)	H46D—C46B—H46E	109.5
C25—C24—H24	120	C43—C46B—H46F	109.5
C23—C24—H24	120	H46D—C46B—H46F	109.5
C24—C25—C21	119.0 (3)	H46E—C46B—H46F	109.5
C24—C25—C26	135.1 (3)	C50B—C47—C48B	110.5 (6)
C21—C25—C26	105.9 (2)	C50B—C47—C49B	109.9 (7)
C27—C26—C15	118.9 (3)	C48B—C47—C49B	109.8 (6)
C27—C26—C25	131.9 (3)	C48A—C47—C50A	108.9 (4)
C15—C26—C25	109.3 (2)	C48A—C47—C49A	108.0 (4)
C26—C27—C2	121.0 (3)	C50A—C47—C49A	107.0 (4)
C26—C27—C28	130.6 (3)	C50B—C47—C23	112.8 (9)
C2—C27—C28	108.4 (2)	C48B—C47—C23	108.5 (8)
O2—C28—N1	124.1 (3)	C49B—C47—C23	105.1 (9)
O2—C28—C27	130.3 (3)	C48A—C47—C23	109.6 (5)
N1—C28—C27	105.6 (2)	C50A—C47—C23	111.4 (4)
C30—C29—C34	120.2 (3)	C49A—C47—C23	111.8 (3)
C30—C29—N1	119.5 (3)	C47—C48A—H48A	109.5
C34—C29—N1	120.3 (3)	C47—C48A—H48B	109.5
C29—C30—C31	120.0 (3)	H48A—C48A—H48B	109.5
C29—C30—H30	120	C47—C48A—H48C	109.5
C31—C30—H30	120	H48A—C48A—H48C	109.5
C32—C31—C30	120.0 (3)	H48B—C48A—H48C	109.5
C32—C31—H31	120	C47—C49A—H49A	109.5
C30—C31—H31	120	C47—C49A—H49B	109.5
C31—C32—C33	120.3 (3)	H49A—C49A—H49B	109.5
C31—C32—H32	119.8	C47—C49A—H49C	109.5
C33—C32—H32	119.8	H49A—C49A—H49C	109.5
C32—C33—C34	120.3 (3)	H49B—C49A—H49C	109.5
C32—C33—H33	119.9	C47—C50A—H50A	109.5
C34—C33—H33	119.9	C47—C50A—H50B	109.5
C29—C34—C33	119.2 (3)	H50A—C50A—H50B	109.5
C29—C34—H34	120.4	C47—C50A—H50C	109.5
C33—C34—H34	120.4	H50A—C50A—H50C	109.5
C36—C35—C38	111.4 (4)	H50B—C50A—H50C	109.5
C36—C35—C6	108.6 (3)	C47—C48B—H48D	109.5
C38—C35—C6	112.7 (3)	C47—C48B—H48E	109.5
C36—C35—C37	108.8 (4)	H48D—C48B—H48E	109.5
C38—C35—C37	105.2 (3)	C47—C48B—H48F	109.5
C6—C35—C37	110.1 (3)	H48D—C48B—H48F	109.5
C35—C36—H36A	109.5	H48E—C48B—H48F	109.5
C35—C36—H36B	109.5	C47—C49B—H49D	109.5
H36A—C36—H36B	109.5	C47—C49B—H49E	109.5
C35—C36—H36C	109.5	H49D—C49B—H49E	109.5
H36A—C36—H36C	109.5	C47—C49B—H49F	109.5
H36B—C36—H36C	109.5	H49D—C49B—H49F	109.5
C35—C37—H37A	109.5	H49E—C49B—H49F	109.5
C35—C37—H37B	109.5	C47—C50B—H50D	109.5
H37A—C37—H37B	109.5	C47—C50B—H50E	109.5
C35—C37—H37C	109.5	H50D—C50B—H50E	109.5
H37A—C37—H37C	109.5	C47—C50B—H50F	109.5
H37B—C37—H37C	109.5	H50D—C50B—H50F	109.5
C35—C38—H38A	109.5	H50E—C50B—H50F	109.5
C35—C38—H38B	109.5	C28—N1—C1	111.9 (2)
H38A—C38—H38B	109.5	C28—N1—C29	124.0 (2)
C35—C38—H38C	109.5	C1—N1—C29	123.9 (2)
H38A—C38—H38C	109.5

O1—C1—C2—C3	1.2 (5)	C20—C21—C25—C24	−0.9 (4)
N1—C1—C2—C3	−178.7 (3)	C16—C21—C25—C24	−179.9 (3)
O1—C1—C2—C27	−177.3 (3)	C20—C21—C25—C26	178.6 (3)
N1—C1—C2—C27	2.8 (3)	C16—C21—C25—C26	−0.5 (3)
C27—C2—C3—C14	1.3 (4)	C14—C15—C26—C27	−0.5 (4)
C1—C2—C3—C14	−177.1 (3)	C16—C15—C26—C27	178.8 (3)
C27—C2—C3—C4	−176.2 (3)	C14—C15—C26—C25	179.7 (3)
C1—C2—C3—C4	5.4 (5)	C16—C15—C26—C25	−0.9 (3)
C2—C3—C4—C5	0.2 (6)	C24—C25—C26—C27	0.5 (6)
C14—C3—C4—C5	−177.5 (3)	C21—C25—C26—C27	−178.8 (3)
C2—C3—C4—C9	178.4 (3)	C24—C25—C26—C15	−179.8 (3)
C14—C3—C4—C9	0.7 (3)	C21—C25—C26—C15	0.9 (3)
C9—C4—C5—C6	1.8 (4)	C15—C26—C27—C2	0.6 (4)
C3—C4—C5—C6	179.8 (3)	C25—C26—C27—C2	−179.7 (3)
C4—C5—C6—C7	−2.4 (5)	C15—C26—C27—C28	−179.1 (3)
C4—C5—C6—C35	−179.6 (3)	C25—C26—C27—C28	0.6 (6)
C5—C6—C7—C8	1.3 (5)	C3—C2—C27—C26	−1.0 (4)
C35—C6—C7—C8	178.3 (3)	C1—C2—C27—C26	177.6 (3)
C6—C7—C8—C9	0.5 (5)	C3—C2—C27—C28	178.7 (3)
C6—C7—C8—C10	−179.4 (3)	C1—C2—C27—C28	−2.6 (3)
C7—C8—C9—C4	−1.2 (4)	C26—C27—C28—O2	1.6 (6)
C10—C8—C9—C4	178.7 (3)	C2—C27—C28—O2	−178.1 (3)
C7—C8—C9—C13	179.6 (3)	C26—C27—C28—N1	−178.8 (3)
C10—C8—C9—C13	−0.5 (4)	C2—C27—C28—N1	1.5 (3)
C5—C4—C9—C8	0.1 (4)	C34—C29—C30—C31	0.2 (5)
C3—C4—C9—C8	−178.5 (3)	N1—C29—C30—C31	178.6 (3)
C5—C4—C9—C13	179.3 (3)	C29—C30—C31—C32	−0.3 (5)
C3—C4—C9—C13	0.8 (3)	C30—C31—C32—C33	0.5 (6)
C9—C8—C10—C11	1.7 (4)	C31—C32—C33—C34	−0.7 (6)
C7—C8—C10—C11	−178.4 (3)	C30—C29—C34—C33	−0.4 (5)
C8—C10—C11—C12	−1.2 (5)	N1—C29—C34—C33	−178.8 (3)
C8—C10—C11—C39	178.8 (3)	C32—C33—C34—C29	0.6 (6)
C10—C11—C12—C13	−0.7 (5)	C7—C6—C35—C36	−104.6 (4)
C39—C11—C12—C13	179.3 (3)	C5—C6—C35—C36	72.4 (4)
C11—C12—C13—C9	1.8 (4)	C7—C6—C35—C38	19.4 (5)
C11—C12—C13—C14	−176.2 (3)	C5—C6—C35—C38	−163.6 (3)
C8—C9—C13—C12	−1.3 (5)	C7—C6—C35—C37	136.4 (3)
C4—C9—C13—C12	179.5 (3)	C5—C6—C35—C37	−46.6 (4)
C8—C9—C13—C14	177.4 (3)	C10—C11—C39—C41	−1.0 (4)
C4—C9—C13—C14	−1.9 (3)	C12—C11—C39—C41	178.9 (3)
C2—C3—C14—C15	−1.1 (4)	C10—C11—C39—C42	−121.0 (3)
C4—C3—C14—C15	176.9 (3)	C12—C11—C39—C42	59.0 (4)
C2—C3—C14—C13	−179.9 (2)	C10—C11—C39—C40	118.9 (3)
C4—C3—C14—C13	−1.8 (3)	C12—C11—C39—C40	−61.1 (4)
C12—C13—C14—C15	2.0 (6)	C19—C18—C43—C46A	−177.2 (5)
C9—C13—C14—C15	−176.2 (3)	C17—C18—C43—C46A	2.8 (6)
C12—C13—C14—C3	−179.6 (3)	C19—C18—C43—C45B	−4.2 (6)
C9—C13—C14—C3	2.2 (3)	C17—C18—C43—C45B	175.8 (5)
C3—C14—C15—C26	0.8 (4)	C19—C18—C43—C45A	−51.3 (5)
C13—C14—C15—C26	179.1 (3)	C17—C18—C43—C45A	128.6 (5)
C3—C14—C15—C16	−178.4 (3)	C19—C18—C43—C44B	121.9 (5)
C13—C14—C15—C16	−0.1 (6)	C17—C18—C43—C44B	−58.2 (6)
C14—C15—C16—C17	2.6 (6)	C19—C18—C43—C46B	−123.7 (5)
C26—C15—C16—C17	−176.6 (3)	C17—C18—C43—C46B	56.2 (6)
C14—C15—C16—C21	179.9 (3)	C19—C18—C43—C44A	62.9 (5)
C26—C15—C16—C21	0.6 (3)	C17—C18—C43—C44A	−117.2 (5)
C21—C16—C17—C18	1.1 (4)	C22—C23—C47—C50B	134.6 (17)
C15—C16—C17—C18	178.2 (3)	C24—C23—C47—C50B	−45.8 (17)
C16—C17—C18—C19	−0.6 (5)	C22—C23—C47—C48B	11.8 (17)
C16—C17—C18—C43	179.4 (3)	C24—C23—C47—C48B	−168.6 (17)
C17—C18—C19—C20	0.1 (5)	C22—C23—C47—C49B	−105.6 (16)
C43—C18—C19—C20	−180.0 (3)	C24—C23—C47—C49B	74.0 (17)
C18—C19—C20—C21	−0.1 (4)	C22—C23—C47—C48A	−70.6 (5)
C18—C19—C20—C22	−178.7 (3)	C24—C23—C47—C48A	108.9 (5)
C22—C20—C21—C25	0.5 (4)	C22—C23—C47—C50A	50.0 (5)
C19—C20—C21—C25	−178.3 (3)	C24—C23—C47—C50A	−130.5 (5)
C22—C20—C21—C16	179.4 (3)	C22—C23—C47—C49A	169.7 (4)
C19—C20—C21—C16	0.7 (4)	C24—C23—C47—C49A	−10.8 (5)
C17—C16—C21—C20	−1.2 (4)	O2—C28—N1—C1	180.0 (3)
C15—C16—C21—C20	−179.1 (3)	C27—C28—N1—C1	0.3 (3)
C17—C16—C21—C25	177.8 (3)	O2—C28—N1—C29	−5.3 (5)
C15—C16—C21—C25	−0.1 (3)	C27—C28—N1—C29	175.0 (3)
C21—C20—C22—C23	0.0 (4)	O1—C1—N1—C28	178.2 (3)
C19—C20—C22—C23	178.6 (3)	C2—C1—N1—C28	−1.9 (3)
C20—C22—C23—C24	−0.1 (5)	O1—C1—N1—C29	3.5 (4)
C20—C22—C23—C47	179.5 (3)	C2—C1—N1—C29	−176.6 (3)
C22—C23—C24—C25	−0.3 (4)	C30—C29—N1—C28	−116.0 (3)
C47—C23—C24—C25	−179.8 (3)	C34—C29—N1—C28	62.4 (4)
C23—C24—C25—C21	0.7 (4)	C30—C29—N1—C1	58.1 (4)
C23—C24—C25—C26	−178.5 (3)	C34—C29—N1—C1	−123.5 (3)

Experimental details

Crystal data
Chemical formula	C₅₀H₄₉NO₂
M_r	695.9
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	19.155 (3), 10.5762 (14), 19.495 (3)
β (°)	92.382 (3)
V (Å³)	3946.0 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.50 × 0.45 × 0.18

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	36876, 9011, 4306
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.077, 0.243, 1.06
No. of reflections	9011
No. of parameters	534
No. of restraints	60
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.34, −0.25

Computer programs: PROCESS-AUTO (Rigaku, 1998), SIR2004 (Burla et al., 2005), SHELXL2014 (Sheldrick, 2015), Mercury (Macrae et al., 2008), WinGX (Farrugia, 2012).

Acknowledgements

This work was supported financially by JSPS KAKENHI grant No. 15K05482.

References

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