1'-Methyl-4'-(1-naphth-yl)-3''-(1-naphthyl-methyl-ene)acenaphthene-1-spiro-2'-pyrrolidine-3'-spiro-1''-cyclo-hexane-2,2''-dione.

In the title compound, C(42)H(33)NO(2), the six-membered cyclo-hexa-none ring adopts a slightly distorted chair conformation and the five-membered pyrrolidine ring is in an envelope conformation. The mol-ecular structure features four intra-molecular C-H⋯O inter-actions and an intra-molecular C-H⋯π inter-action. Furthermore, the crystal packing is stabilized by an inter-molecular C-H⋯O and three inter-molecular C-H⋯π inter-actions.

Related literature

For the biological importance of pyran derivatives, see: Babu & Raghunathan (2007 ▶); Chande et al. (2005 ▶); De March et al. (2002 ▶); Escolano & Jones (2000 ▶); Fejes et al. (2001 ▶); Poornachandran & Raghunathan (2006 ▶); Raj & Raghunathan (2001 ▶); Raj et al. (2003 ▶); Pinna et al. (2002 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bonding inter­actions, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C42H33NO2

M = 583.69

Monoclinic,

a = 12.4398 (8) Å

b = 17.3501 (11) Å

c = 14.4685 (9) Å

β = 90.728 (17)°

V = 3122.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 293 (2) K

0.22 × 0.18 × 0.16 mm

Data collection

Nonius MACH3 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.943, T max = 0.986

6169 measured reflections

5489 independent reflections

3098 reflections with I > 2σ(I)

R int = 0.022

3 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.164

S = 1.02

5489 reflections

407 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.24 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 Express; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000 ▶); program(s) used to refine structure: SHELXTL/PC; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL/PC.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807061387/sj2436sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807061387/sj2436Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C42H33NO2	F000 = 1232
Mr = 583.69	Dx = 1.242 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 12.4398 (8) Å	θ = 9.4–13.6º
b = 17.3501 (11) Å	µ = 0.08 mm−1
c = 14.4685 (9) Å	T = 293 (2) K
β = 90.728 (17)º	Block, pale yellow
V = 3122.5 (3) Å3	0.22 × 0.18 × 0.16 mm
Z = 4

Nonius MACH3 sealed tube diffractometer	Rint = 0.022
Radiation source: fine-focus sealed tube	θmax = 25.0º
Monochromator: graphite	θmin = 2.0º
T = 293(2) K	h = 0→14
ω–2θ scans	k = −1→20
Absorption correction: ψ scan(North et al., 1968)	l = −17→17
Tmin = 0.943, Tmax = 0.986	3 standard reflections
6169 measured reflections	every 60 min
5489 independent reflections	intensity decay: none
3098 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H-atom parameters constrained
wR(F2) = 0.164	w = 1/[σ2(Fo2) + (0.0776P)2 + 0.7574P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
5489 reflections	Δρmax = 0.31 e Å−3
407 parameters	Δρmin = −0.23 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
C31	0.40070 (19)	0.14164 (18)	1.02686 (18)	0.0648 (7)
C23	0.4443 (2)	0.26622 (19)	0.9649 (2)	0.0809 (8)
H23	0.4609	0.2977	0.9150	0.097*
C96	0.4902 (5)	0.3913 (2)	0.4021 (3)	0.1277 (18)
H96	0.4749	0.4354	0.3680	0.153*
C26	0.3922 (2)	0.1747 (2)	1.1160 (2)	0.0769 (8)
C1	0.4091 (2)	0.13447 (13)	0.69369 (16)	0.0542 (6)
C76	0.1547 (2)	−0.07341 (14)	0.80960 (19)	0.0681 (7)
C80	0.1785 (2)	−0.02788 (13)	0.73238 (17)	0.0573 (6)
C22	0.4280 (2)	0.18940 (17)	0.95041 (18)	0.0653 (7)
C95	0.4139 (4)	0.3296 (2)	0.4043 (2)	0.0971 (11)
C27	0.3649 (3)	0.1256 (3)	1.1910 (2)	0.1050 (12)
H27	0.3605	0.1462	1.2502	0.126*
O1	0.11519 (16)	0.06038 (12)	0.52182 (13)	0.0769 (5)
C98	0.6076 (3)	0.3212 (2)	0.5014 (3)	0.1121 (13)
H98	0.6728	0.3183	0.5334	0.135*
C99	0.5353 (3)	0.26097 (18)	0.5068 (2)	0.0833 (9)
H99	0.5523	0.2182	0.5429	0.100*
C7	0.27886 (19)	0.04002 (13)	0.61796 (16)	0.0553 (6)
C2	0.37832 (18)	0.17015 (14)	0.78418 (16)	0.0539 (6)
N2	0.34277 (17)	0.00032 (12)	0.54755 (15)	0.0670 (6)
C29	0.3521 (3)	0.0180 (2)	1.0906 (2)	0.0988 (10)
H29	0.3383	−0.0342	1.0818	0.119*
C21	0.4406 (2)	0.15553 (16)	0.85697 (18)	0.0654 (7)
H21	0.4971	0.1211	0.8489	0.079*
C25	0.4114 (2)	0.2541 (3)	1.1274 (2)	0.0935 (11)
H25	0.4069	0.2760	1.1859	0.112*
C28	0.3450 (3)	0.0490 (3)	1.1782 (3)	0.1136 (13)
H28	0.3269	0.0179	1.2280	0.136*
C5	0.2369 (2)	0.18867 (14)	0.62718 (16)	0.0554 (6)
H5A	0.2676	0.2383	0.6114	0.067*
H5B	0.1783	0.1785	0.5840	0.067*
C8	0.3543 (2)	0.05347 (16)	0.47035 (19)	0.0742 (8)
H8A	0.2881	0.0573	0.4345	0.089*
H8B	0.4119	0.0375	0.4300	0.089*
C3	0.2801 (2)	0.22026 (16)	0.78963 (17)	0.0640 (7)
H3A	0.2994	0.2730	0.7748	0.077*
H3B	0.2533	0.2195	0.8523	0.077*
C92	0.2646 (3)	0.2095 (2)	0.4123 (2)	0.0912 (10)
H92	0.2142	0.1699	0.4143	0.109*
C30	0.3787 (2)	0.06225 (19)	1.0169 (2)	0.0760 (8)
H30	0.3826	0.0398	0.9586	0.091*
C75	0.0458 (3)	−0.09408 (18)	0.8194 (2)	0.0869 (9)
H75	0.0254	−0.1231	0.8702	0.104*
C74	−0.0301 (3)	−0.07252 (19)	0.7561 (3)	0.0910 (10)
H74	−0.1010	−0.0877	0.7647	0.109*
C72	0.1000 (2)	−0.00583 (15)	0.66737 (17)	0.0603 (6)
C71	0.1555 (2)	0.03648 (14)	0.59335 (18)	0.0589 (6)
C94	0.3165 (5)	0.3341 (3)	0.3563 (3)	0.1228 (17)
H94	0.3022	0.3779	0.3212	0.147*
C93	0.2409 (4)	0.2770 (3)	0.3584 (2)	0.1118 (13)
H93	0.1762	0.2818	0.3260	0.134*
C9	0.3810 (2)	0.12982 (14)	0.51825 (17)	0.0609 (7)
H9	0.4585	0.1292	0.5311	0.073*
C24	0.4365 (2)	0.2991 (2)	1.0536 (3)	0.0944 (11)
H24	0.4485	0.3516	1.0618	0.113*
C97	0.5839 (5)	0.3858 (3)	0.4489 (4)	0.143 (2)
H97	0.6334	0.4259	0.4459	0.171*
C100	0.4371 (3)	0.26315 (16)	0.45885 (19)	0.0763 (9)
C6	0.32354 (19)	0.12593 (13)	0.61563 (15)	0.0528 (6)
C73	−0.0050 (2)	−0.02810 (17)	0.6779 (2)	0.0769 (8)
H73	−0.0578	−0.0143	0.6349	0.092*
C91	0.3588 (2)	0.20153 (16)	0.46075 (18)	0.0699 (8)
C4	0.19211 (19)	0.19324 (15)	0.72368 (16)	0.0580 (6)
H4A	0.1663	0.1430	0.7425	0.070*
H4B	0.1322	0.2290	0.7247	0.070*
C77	0.2434 (3)	−0.09586 (15)	0.8653 (2)	0.0808 (9)
H77	0.2324	−0.1236	0.9194	0.097*
C78	0.3445 (3)	−0.07686 (16)	0.8400 (2)	0.0829 (9)
H78	0.4019	−0.0943	0.8761	0.100*
C79	0.3667 (2)	−0.03199 (15)	0.7614 (2)	0.0736 (8)
H79	0.4372	−0.0209	0.7456	0.088*
C70	0.2830 (2)	−0.00505 (13)	0.70856 (17)	0.0572 (6)
C10	0.3049 (3)	−0.07619 (17)	0.5196 (2)	0.0916 (10)
H10A	0.2343	−0.0720	0.4925	0.137*
H10B	0.3023	−0.1092	0.5728	0.137*
H10C	0.3532	−0.0976	0.4753	0.137*
O2	0.50114 (14)	0.11274 (11)	0.68220 (12)	0.0725 (5)

	U11	U22	U33	U12	U13	U23
C31	0.0473 (14)	0.090 (2)	0.0573 (16)	0.0081 (13)	−0.0047 (11)	−0.0089 (15)
C23	0.081 (2)	0.082 (2)	0.079 (2)	−0.0038 (16)	−0.0039 (16)	−0.0090 (17)
C96	0.202 (5)	0.071 (3)	0.113 (4)	0.006 (3)	0.079 (4)	0.021 (2)
C26	0.0566 (16)	0.111 (3)	0.0627 (18)	0.0165 (16)	−0.0038 (13)	−0.0151 (18)
C1	0.0554 (15)	0.0486 (14)	0.0588 (15)	−0.0017 (11)	0.0139 (11)	0.0046 (11)
C76	0.095 (2)	0.0458 (14)	0.0639 (17)	−0.0112 (14)	0.0151 (15)	−0.0039 (13)
C80	0.0722 (17)	0.0434 (13)	0.0566 (15)	−0.0049 (12)	0.0085 (13)	−0.0059 (12)
C22	0.0543 (15)	0.0771 (19)	0.0642 (17)	0.0040 (13)	−0.0078 (12)	−0.0079 (15)
C95	0.145 (3)	0.072 (2)	0.076 (2)	0.024 (2)	0.050 (2)	0.0145 (18)
C27	0.091 (2)	0.165 (4)	0.060 (2)	0.020 (3)	0.0118 (17)	−0.009 (2)
O1	0.0827 (13)	0.0851 (13)	0.0625 (12)	−0.0054 (10)	−0.0116 (10)	0.0023 (10)
C98	0.121 (3)	0.087 (3)	0.130 (3)	−0.026 (2)	0.062 (2)	−0.022 (2)
C99	0.090 (2)	0.0696 (19)	0.092 (2)	−0.0005 (17)	0.0401 (19)	−0.0078 (16)
C7	0.0601 (15)	0.0514 (14)	0.0547 (14)	−0.0004 (11)	0.0092 (11)	−0.0004 (11)
C2	0.0542 (14)	0.0565 (15)	0.0513 (14)	−0.0078 (12)	0.0064 (11)	0.0007 (11)
N2	0.0743 (14)	0.0531 (12)	0.0740 (14)	0.0009 (11)	0.0165 (11)	−0.0073 (11)
C29	0.099 (2)	0.110 (3)	0.088 (2)	0.001 (2)	0.0126 (19)	0.013 (2)
C21	0.0592 (15)	0.0738 (18)	0.0633 (16)	0.0051 (13)	0.0011 (13)	−0.0059 (14)
C25	0.071 (2)	0.129 (3)	0.080 (2)	0.012 (2)	−0.0083 (17)	−0.039 (2)
C28	0.109 (3)	0.148 (4)	0.084 (3)	0.015 (3)	0.023 (2)	0.025 (3)
C5	0.0639 (15)	0.0500 (14)	0.0525 (14)	0.0019 (11)	0.0053 (11)	0.0007 (11)
C8	0.086 (2)	0.0732 (19)	0.0637 (17)	−0.0031 (15)	0.0229 (15)	−0.0104 (14)
C3	0.0688 (16)	0.0680 (17)	0.0553 (15)	0.0050 (13)	0.0086 (12)	−0.0020 (13)
C92	0.110 (3)	0.106 (3)	0.0574 (17)	0.025 (2)	0.0134 (17)	0.0077 (17)
C30	0.0715 (18)	0.090 (2)	0.0669 (18)	0.0040 (16)	0.0056 (14)	−0.0005 (16)
C75	0.110 (3)	0.0688 (19)	0.082 (2)	−0.0224 (19)	0.030 (2)	−0.0024 (17)
C74	0.082 (2)	0.090 (2)	0.102 (3)	−0.0288 (19)	0.036 (2)	−0.019 (2)
C72	0.0638 (16)	0.0558 (15)	0.0615 (15)	−0.0080 (12)	0.0086 (12)	−0.0101 (12)
C71	0.0660 (16)	0.0539 (15)	0.0568 (15)	−0.0013 (12)	0.0014 (12)	−0.0084 (13)
C94	0.190 (5)	0.104 (3)	0.076 (2)	0.057 (3)	0.057 (3)	0.029 (2)
C93	0.134 (3)	0.134 (4)	0.068 (2)	0.052 (3)	0.020 (2)	0.011 (2)
C9	0.0692 (16)	0.0583 (16)	0.0556 (15)	−0.0022 (12)	0.0161 (12)	−0.0016 (12)
C24	0.076 (2)	0.092 (2)	0.115 (3)	0.0027 (18)	−0.014 (2)	−0.038 (2)
C97	0.194 (6)	0.089 (3)	0.147 (5)	−0.026 (4)	0.082 (4)	−0.004 (3)
C100	0.110 (2)	0.0607 (18)	0.0590 (17)	0.0103 (17)	0.0449 (17)	0.0025 (14)
C6	0.0600 (14)	0.0499 (14)	0.0486 (13)	−0.0029 (11)	0.0101 (11)	0.0006 (11)
C73	0.0668 (18)	0.083 (2)	0.082 (2)	−0.0135 (15)	0.0081 (15)	−0.0172 (17)
C91	0.088 (2)	0.0700 (18)	0.0520 (15)	0.0099 (16)	0.0259 (15)	0.0033 (13)
C4	0.0556 (14)	0.0620 (15)	0.0566 (14)	0.0066 (12)	0.0081 (11)	0.0004 (12)
C77	0.130 (3)	0.0462 (16)	0.0663 (18)	−0.0080 (17)	0.0000 (19)	0.0075 (13)
C78	0.109 (3)	0.0551 (17)	0.084 (2)	0.0058 (17)	−0.0210 (19)	0.0105 (16)
C79	0.0805 (19)	0.0548 (16)	0.085 (2)	0.0013 (14)	−0.0076 (16)	0.0097 (15)
C70	0.0646 (16)	0.0441 (13)	0.0628 (15)	−0.0005 (12)	0.0034 (12)	0.0024 (12)
C10	0.105 (2)	0.0616 (19)	0.109 (3)	−0.0059 (17)	0.0251 (19)	−0.0234 (17)
O2	0.0570 (11)	0.0907 (14)	0.0700 (12)	0.0072 (10)	0.0124 (9)	−0.0036 (10)

C31—C30	1.411 (4)	C25—H25	0.9300
C31—C26	1.417 (4)	C28—H28	0.9300
C31—C22	1.427 (4)	C5—C4	1.512 (3)
C23—C22	1.364 (4)	C5—C6	1.543 (3)
C23—C24	1.409 (4)	C5—H5A	0.9700
C23—H23	0.9300	C5—H5B	0.9700
C96—C97	1.344 (7)	C8—C9	1.530 (4)
C96—C95	1.431 (6)	C8—H8A	0.9700
C96—H96	0.9300	C8—H8B	0.9700
C26—C25	1.407 (5)	C3—C4	1.517 (3)
C26—C27	1.425 (5)	C3—H3A	0.9700
C1—O2	1.218 (3)	C3—H3B	0.9700
C1—C2	1.502 (3)	C92—C91	1.365 (4)
C1—C6	1.549 (3)	C92—C93	1.436 (5)
C76—C80	1.403 (3)	C92—H92	0.9300
C76—C75	1.411 (4)	C30—H30	0.9300
C76—C77	1.412 (4)	C75—C74	1.359 (4)
C80—C72	1.401 (3)	C75—H75	0.9300
C80—C70	1.405 (3)	C74—C73	1.407 (4)
C22—C21	1.484 (4)	C74—H74	0.9300
C95—C94	1.391 (6)	C72—C73	1.373 (4)
C95—C100	1.425 (4)	C72—C71	1.477 (4)
C27—C28	1.363 (5)	C94—C93	1.366 (6)
C27—H27	0.9300	C94—H94	0.9300
O1—C71	1.217 (3)	C93—H93	0.9300
C98—C99	1.381 (4)	C9—C91	1.520 (4)
C98—C97	1.384 (6)	C9—C6	1.589 (3)
C98—H98	0.9300	C9—H9	0.9800
C99—C100	1.398 (4)	C24—H24	0.9300
C99—H99	0.9300	C97—H97	0.9300
C7—N2	1.471 (3)	C100—C91	1.447 (4)
C7—C70	1.527 (3)	C73—H73	0.9300
C7—C71	1.572 (3)	C4—H4A	0.9700
C7—C6	1.591 (3)	C4—H4B	0.9700
C2—C21	1.324 (3)	C77—C78	1.355 (4)
C2—C3	1.503 (3)	C77—H77	0.9300
N2—C8	1.457 (3)	C78—C79	1.408 (4)
N2—C10	1.464 (3)	C78—H78	0.9300
C29—C30	1.358 (4)	C79—C70	1.366 (3)
C29—C28	1.381 (5)	C79—H79	0.9300
C29—H29	0.9300	C10—H10A	0.9600
C21—H21	0.9300	C10—H10B	0.9600
C25—C24	1.363 (5)	C10—H10C	0.9600
C30—C31—C26	118.2 (3)	H3A—C3—H3B	108.0
C30—C31—C22	122.3 (3)	C91—C92—C93	122.0 (4)
C26—C31—C22	119.5 (3)	C91—C92—H92	119.0
C22—C23—C24	121.6 (3)	C93—C92—H92	119.0
C22—C23—H23	119.2	C29—C30—C31	121.3 (3)
C24—C23—H23	119.2	C29—C30—H30	119.3
C97—C96—C95	120.5 (5)	C31—C30—H30	119.3
C97—C96—H96	119.7	C74—C75—C76	121.5 (3)
C95—C96—H96	119.7	C74—C75—H75	119.2
C25—C26—C31	119.2 (3)	C76—C75—H75	119.2
C25—C26—C27	122.6 (3)	C75—C74—C73	122.2 (3)
C31—C26—C27	118.2 (3)	C75—C74—H74	118.9
O2—C1—C2	119.8 (2)	C73—C74—H74	118.9
O2—C1—C6	120.6 (2)	C73—C72—C80	120.4 (3)
C2—C1—C6	119.6 (2)	C73—C72—C71	132.4 (3)
C80—C76—C75	115.8 (3)	C80—C72—C71	107.1 (2)
C80—C76—C77	116.0 (3)	O1—C71—C72	126.5 (2)
C75—C76—C77	128.1 (3)	O1—C71—C7	124.7 (2)
C72—C80—C76	122.4 (2)	C72—C71—C7	108.6 (2)
C72—C80—C70	113.4 (2)	C93—C94—C95	122.9 (4)
C76—C80—C70	124.0 (2)	C93—C94—H94	118.5
C23—C22—C31	119.0 (3)	C95—C94—H94	118.5
C23—C22—C21	120.7 (3)	C94—C93—C92	117.9 (4)
C31—C22—C21	120.3 (3)	C94—C93—H93	121.1
C94—C95—C100	119.4 (4)	C92—C93—H93	121.1
C94—C95—C96	121.4 (4)	C91—C9—C8	115.1 (2)
C100—C95—C96	119.2 (4)	C91—C9—C6	116.1 (2)
C28—C27—C26	121.6 (3)	C8—C9—C6	105.51 (19)
C28—C27—H27	119.2	C91—C9—H9	106.5
C26—C27—H27	119.2	C8—C9—H9	106.5
C99—C98—C97	120.7 (5)	C6—C9—H9	106.5
C99—C98—H98	119.7	C25—C24—C23	120.0 (3)
C97—C98—H98	119.7	C25—C24—H24	120.0
C98—C99—C100	121.1 (4)	C23—C24—H24	120.0
C98—C99—H99	119.4	C96—C97—C98	120.7 (5)
C100—C99—H99	119.4	C96—C97—H97	119.7
N2—C7—C70	110.0 (2)	C98—C97—H97	119.7
N2—C7—C71	111.06 (19)	C99—C100—C95	117.8 (3)
C70—C7—C71	101.33 (19)	C99—C100—C91	123.7 (3)
N2—C7—C6	103.41 (18)	C95—C100—C91	118.5 (3)
C70—C7—C6	119.34 (19)	C5—C6—C1	109.17 (19)
C71—C7—C6	111.84 (19)	C5—C6—C9	112.88 (19)
C21—C2—C1	117.4 (2)	C1—C6—C9	109.24 (19)
C21—C2—C3	122.5 (2)	C5—C6—C7	114.45 (19)
C1—C2—C3	120.1 (2)	C1—C6—C7	108.13 (18)
C8—N2—C10	113.4 (2)	C9—C6—C7	102.69 (18)
C8—N2—C7	107.08 (19)	C72—C73—C74	117.7 (3)
C10—N2—C7	116.2 (2)	C72—C73—H73	121.2
C30—C29—C28	121.3 (4)	C74—C73—H73	121.2
C30—C29—H29	119.3	C92—C91—C100	119.3 (3)
C28—C29—H29	119.3	C92—C91—C9	120.8 (3)
C2—C21—C22	125.5 (2)	C100—C91—C9	119.8 (3)
C2—C21—H21	117.2	C5—C4—C3	109.0 (2)
C22—C21—H21	117.2	C5—C4—H4A	109.9
C24—C25—C26	120.7 (3)	C3—C4—H4A	109.9
C24—C25—H25	119.7	C5—C4—H4B	109.9
C26—C25—H25	119.7	C3—C4—H4B	109.9
C27—C28—C29	119.4 (4)	H4A—C4—H4B	108.3
C27—C28—H28	120.3	C78—C77—C76	119.9 (3)
C29—C28—H28	120.3	C78—C77—H77	120.0
C4—C5—C6	113.8 (2)	C76—C77—H77	120.0
C4—C5—H5A	108.8	C77—C78—C79	123.0 (3)
C6—C5—H5A	108.8	C77—C78—H78	118.5
C4—C5—H5B	108.8	C79—C78—H78	118.5
C6—C5—H5B	108.8	C70—C79—C78	119.0 (3)
H5A—C5—H5B	107.7	C70—C79—H79	120.5
N2—C8—C9	102.9 (2)	C78—C79—H79	120.5
N2—C8—H8A	111.2	C79—C70—C80	117.8 (2)
C9—C8—H8A	111.2	C79—C70—C7	132.3 (2)
N2—C8—H8B	111.2	C80—C70—C7	109.5 (2)
C9—C8—H8B	111.2	N2—C10—H10A	109.5
H8A—C8—H8B	109.1	N2—C10—H10B	109.5
C2—C3—C4	111.6 (2)	H10A—C10—H10B	109.5
C2—C3—H3A	109.3	N2—C10—H10C	109.5
C4—C3—H3A	109.3	H10A—C10—H10C	109.5
C2—C3—H3B	109.3	H10B—C10—H10C	109.5
C4—C3—H3B	109.3

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5B···O1	0.97	2.37	3.084 (3)	130
C8—H8A···O1	0.97	2.51	3.078 (4)	117
C9—H9···O2	0.98	2.26	2.803 (3)	114
C21—H21···O2	0.93	2.42	2.750 (3)	101
C73—H73···O1i	0.93	2.50	3.231 (4)	136
C4—H4A···Cg1	0.97	2.64	3.337 (3)	129
C75—H75···Cg2ii	0.93	2.74	3.646 (3)	164
C78—H78···Cg3iii	0.93	2.82	3.622 (4)	145
C96—H96···Cg4iv	0.93	2.96	3.742 (4)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of the C7/C70–72/C80, C95–C100, C26–C31 and C72–76/80 rings.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5B⋯O1	0.97	2.37	3.084 (3)	130
C8—H8A⋯O1	0.97	2.51	3.078 (4)	117
C9—H9⋯O2	0.98	2.26	2.803 (3)	114
C21—H21⋯O2	0.93	2.42	2.750 (3)	101
C73—H73⋯O1i	0.93	2.50	3.231 (4)	136
C4—H4A⋯Cg1	0.97	2.64	3.337 (3)	129
C75—H75⋯Cg2ii	0.93	2.74	3.646 (3)	164
C78—H78⋯Cg3iii	0.93	2.82	3.622 (4)	145
C96—H96⋯Cg4iv	0.93	2.96	3.742 (4)	142

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .