{2,7-Dieth-oxy-8-[(naphthalen-1-yl)carbon-yl]naph-thalen-1-yl}(naphthalen-1-yl)methanone.

In the title compound, C36H28O4, the 1-naphthoyl groups at the 1- and 8-positions of the central 2,7-dieth-oxy-naphthalene ring system are aligned almost anti-parallel and make a dihedral angle of 76.59 (4)°. The dihedral angles between the central 2,7-dieth-oxy-naphthalene ring system and the terminal naphthalene ring systems are 86.48 (4) and 83.97 (4)°. In the crystal, C-H⋯π inter-actions between the central naphthalene ring systems and the naphthoyl groups are observed along the a axis, with the mol-ecules forming a columnar structure. The columns are linked into chains parallel to the b axis by C-H⋯O inter-actions.

Related literature

For electrophilic aroylation of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Nakaema et al. (2008 ▶); Tsumuki et al. (2011 ▶); Sakamoto et al. (2012 ▶); Isogai et al. (2013 ▶); Tsumuki et al. (2013 ▶); Yoshiwaka et al. (2013 ▶).

Experimental

Crystal data

C36H28O4

M = 524.58

Triclinic,

a = 8.76532 (16) Å

b = 11.4266 (2) Å

c = 14.1972 (3) Å

α = 99.080 (1)°

β = 99.036 (1)°

γ = 104.277 (1)°

V = 1331.94 (4) Å3

Z = 2

Cu Kα radiation

μ = 0.67 mm−1

T = 193 K

0.60 × 0.40 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.689, T max = 0.877

24143 measured reflections

4800 independent reflections

4142 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.106

S = 1.07

4800 reflections

364 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813005710/pk2467sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813005710/pk2467Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813005710/pk2467Isup3.cml

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

C36H28O4	Z = 2
Mr = 524.58	F(000) = 552
Triclinic, P1	Dx = 1.308 Mg m−3
Hall symbol: -P 1	Melting point = 506.6–508.4 K
a = 8.76532 (16) Å	Cu Kα radiation, λ = 1.54187 Å
b = 11.4266 (2) Å	Cell parameters from 20940 reflections
c = 14.1972 (3) Å	θ = 3.2–68.2°
α = 99.080 (1)°	µ = 0.67 mm−1
β = 99.036 (1)°	T = 193 K
γ = 104.277 (1)°	Platelet, colorless
V = 1331.94 (4) Å3	0.60 × 0.40 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	4800 independent reflections
Radiation source: rotating anode	4142 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.043
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −13→13
Tmin = 0.689, Tmax = 0.877	l = −17→17
24143 measured reflections

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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.058P)2 + 0.2087P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max = 0.001
4800 reflections	Δρmax = 0.20 e Å−3
364 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0072 (5)

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
O1	0.08739 (10)	0.64809 (8)	0.66867 (6)	0.0379 (2)
O2	0.19599 (10)	0.86929 (8)	0.83185 (6)	0.0388 (2)
O3	−0.20151 (10)	0.67148 (9)	0.48478 (6)	0.0419 (2)
O4	−0.01872 (10)	0.83966 (9)	1.00812 (6)	0.0429 (2)
C1	−0.13726 (14)	0.73032 (10)	0.65387 (9)	0.0312 (3)
C2	−0.25357 (15)	0.70050 (11)	0.56859 (9)	0.0345 (3)
C3	−0.41501 (15)	0.69700 (12)	0.56983 (10)	0.0399 (3)
H3	−0.4924	0.6770	0.5106	0.048*
C4	−0.45851 (15)	0.72264 (12)	0.65675 (10)	0.0407 (3)
H4	−0.5671	0.7211	0.6576	0.049*
C5	−0.34659 (14)	0.75145 (11)	0.74590 (9)	0.0360 (3)
C6	−0.39763 (15)	0.77691 (13)	0.83424 (10)	0.0429 (3)
H6	−0.5073	0.7742	0.8325	0.052*
C7	−0.29423 (16)	0.80531 (13)	0.92212 (10)	0.0430 (3)
H7	−0.3305	0.8231	0.9810	0.052*
C8	−0.13216 (15)	0.80769 (12)	0.92383 (9)	0.0364 (3)
C9	−0.07595 (14)	0.78095 (11)	0.83942 (9)	0.0313 (3)
C10	−0.18165 (14)	0.75431 (10)	0.74623 (9)	0.0313 (3)
C11	0.02752 (14)	0.72402 (10)	0.63903 (8)	0.0306 (3)
C12	0.11099 (14)	0.81261 (11)	0.58353 (9)	0.0327 (3)
C13	0.11822 (17)	0.93448 (12)	0.61063 (10)	0.0440 (3)
H13	0.0676	0.9596	0.6617	0.053*
C14	0.1996 (2)	1.02299 (13)	0.56390 (13)	0.0560 (4)
H14	0.2063	1.1076	0.5848	0.067*
C15	0.26881 (18)	0.98776 (14)	0.48875 (12)	0.0530 (4)
H15	0.3246	1.0484	0.4581	0.064*
C16	0.25873 (15)	0.86244 (12)	0.45584 (9)	0.0402 (3)
C17	0.31914 (16)	0.82289 (15)	0.37281 (10)	0.0489 (4)
H17	0.3743	0.8826	0.3412	0.059*
C18	0.29954 (16)	0.70146 (15)	0.33786 (10)	0.0481 (4)
H18	0.3374	0.6766	0.2809	0.058*
C19	0.22326 (15)	0.61257 (13)	0.38595 (9)	0.0427 (3)
H19	0.2106	0.5277	0.3615	0.051*
C20	0.16714 (14)	0.64674 (11)	0.46737 (9)	0.0351 (3)
H20	0.1180	0.5853	0.4997	0.042*
C21	0.18097 (13)	0.77222 (11)	0.50452 (8)	0.0325 (3)
C22	0.10078 (14)	0.78898 (10)	0.85622 (8)	0.0307 (3)
C23	0.15239 (14)	0.69517 (11)	0.90702 (8)	0.0321 (3)
C24	0.06855 (16)	0.57328 (11)	0.87330 (9)	0.0385 (3)
H24	−0.0238	0.5518	0.8222	0.046*
C25	0.11646 (19)	0.47971 (13)	0.91269 (11)	0.0484 (3)
H25	0.0583	0.3957	0.8873	0.058*
C26	0.2463 (2)	0.50928 (14)	0.98733 (11)	0.0515 (4)
H26	0.2797	0.4455	1.0128	0.062*
C27	0.33248 (16)	0.63426 (14)	1.02763 (9)	0.0426 (3)
C28	0.46076 (18)	0.66683 (18)	1.10997 (11)	0.0558 (4)
H28	0.4948	0.6036	1.1360	0.067*
C29	0.53555 (17)	0.78660 (18)	1.15211 (10)	0.0583 (4)
H29	0.6198	0.8066	1.2080	0.070*
C30	0.48893 (16)	0.88165 (16)	1.11340 (10)	0.0518 (4)
H30	0.5410	0.9654	1.1437	0.062*
C31	0.36913 (15)	0.85385 (13)	1.03242 (9)	0.0408 (3)
H31	0.3408	0.9188	1.0061	0.049*
C32	0.28633 (14)	0.72967 (12)	0.98702 (8)	0.0351 (3)
C33	−0.31667 (16)	0.62668 (13)	0.39438 (9)	0.0426 (3)
H33A	−0.3755	0.6882	0.3820	0.051*
H33B	−0.3954	0.5489	0.3965	0.051*
C34	−0.2252 (2)	0.60500 (16)	0.31584 (10)	0.0560 (4)
H34A	−0.1664	0.5449	0.3294	0.067*
H34B	−0.1490	0.6829	0.3138	0.067*
H34C	−0.3005	0.5730	0.2529	0.067*
C35	−0.06724 (16)	0.86450 (12)	1.09918 (9)	0.0395 (3)
H35A	−0.1508	0.7922	1.1063	0.047*
H35B	−0.1118	0.9364	1.1028	0.047*
C36	0.07978 (18)	0.89118 (14)	1.17804 (10)	0.0472 (3)
H36A	0.1255	0.8209	1.1717	0.057*
H36B	0.0504	0.9048	1.2419	0.057*
H36C	0.1595	0.9652	1.1721	0.057*

	U11	U22	U33	U12	U13	U23
O1	0.0401 (5)	0.0440 (5)	0.0379 (5)	0.0200 (4)	0.0118 (4)	0.0157 (4)
O2	0.0334 (5)	0.0402 (5)	0.0419 (5)	0.0070 (4)	0.0067 (4)	0.0117 (4)
O3	0.0345 (5)	0.0570 (6)	0.0308 (5)	0.0128 (4)	0.0012 (4)	0.0042 (4)
O4	0.0364 (5)	0.0645 (6)	0.0302 (5)	0.0211 (4)	0.0071 (4)	0.0055 (4)
C1	0.0292 (6)	0.0307 (6)	0.0343 (6)	0.0085 (5)	0.0052 (5)	0.0093 (5)
C2	0.0336 (6)	0.0352 (6)	0.0346 (6)	0.0094 (5)	0.0049 (5)	0.0094 (5)
C3	0.0307 (6)	0.0474 (7)	0.0384 (7)	0.0080 (5)	−0.0011 (5)	0.0119 (6)
C4	0.0268 (6)	0.0497 (8)	0.0474 (7)	0.0108 (5)	0.0055 (5)	0.0169 (6)
C5	0.0287 (6)	0.0412 (7)	0.0405 (7)	0.0112 (5)	0.0070 (5)	0.0132 (5)
C6	0.0296 (6)	0.0597 (8)	0.0467 (8)	0.0186 (6)	0.0125 (5)	0.0177 (6)
C7	0.0386 (7)	0.0600 (8)	0.0387 (7)	0.0223 (6)	0.0144 (5)	0.0144 (6)
C8	0.0337 (6)	0.0440 (7)	0.0345 (6)	0.0150 (5)	0.0059 (5)	0.0108 (5)
C9	0.0301 (6)	0.0331 (6)	0.0337 (6)	0.0122 (5)	0.0073 (5)	0.0091 (5)
C10	0.0292 (6)	0.0313 (6)	0.0353 (6)	0.0099 (5)	0.0059 (5)	0.0104 (5)
C11	0.0311 (6)	0.0336 (6)	0.0257 (5)	0.0091 (5)	0.0033 (4)	0.0041 (5)
C12	0.0274 (6)	0.0352 (6)	0.0343 (6)	0.0083 (5)	0.0016 (5)	0.0088 (5)
C13	0.0447 (7)	0.0376 (7)	0.0500 (8)	0.0126 (6)	0.0082 (6)	0.0093 (6)
C14	0.0584 (9)	0.0336 (7)	0.0743 (11)	0.0085 (6)	0.0098 (8)	0.0168 (7)
C15	0.0466 (8)	0.0470 (8)	0.0667 (10)	0.0039 (6)	0.0119 (7)	0.0298 (7)
C16	0.0292 (6)	0.0499 (8)	0.0415 (7)	0.0067 (5)	0.0026 (5)	0.0206 (6)
C17	0.0341 (7)	0.0743 (10)	0.0429 (8)	0.0104 (6)	0.0093 (6)	0.0312 (7)
C18	0.0372 (7)	0.0768 (11)	0.0331 (7)	0.0175 (7)	0.0084 (5)	0.0155 (7)
C19	0.0342 (7)	0.0552 (8)	0.0363 (7)	0.0126 (6)	0.0048 (5)	0.0044 (6)
C20	0.0283 (6)	0.0410 (7)	0.0340 (6)	0.0067 (5)	0.0042 (5)	0.0084 (5)
C21	0.0233 (5)	0.0415 (7)	0.0317 (6)	0.0071 (5)	0.0006 (4)	0.0128 (5)
C22	0.0300 (6)	0.0348 (6)	0.0265 (6)	0.0098 (5)	0.0049 (5)	0.0034 (5)
C23	0.0303 (6)	0.0391 (6)	0.0311 (6)	0.0136 (5)	0.0102 (5)	0.0089 (5)
C24	0.0417 (7)	0.0396 (7)	0.0356 (6)	0.0119 (5)	0.0100 (5)	0.0086 (5)
C25	0.0640 (9)	0.0384 (7)	0.0488 (8)	0.0193 (6)	0.0170 (7)	0.0132 (6)
C26	0.0662 (10)	0.0569 (9)	0.0508 (8)	0.0367 (8)	0.0221 (7)	0.0259 (7)
C27	0.0406 (7)	0.0661 (9)	0.0345 (7)	0.0275 (6)	0.0158 (5)	0.0210 (6)
C28	0.0453 (8)	0.0967 (13)	0.0415 (8)	0.0351 (8)	0.0136 (6)	0.0318 (8)
C29	0.0339 (7)	0.1093 (14)	0.0337 (7)	0.0193 (8)	0.0065 (6)	0.0219 (8)
C30	0.0329 (7)	0.0773 (10)	0.0369 (7)	0.0036 (7)	0.0087 (6)	0.0046 (7)
C31	0.0311 (6)	0.0548 (8)	0.0358 (7)	0.0099 (6)	0.0092 (5)	0.0079 (6)
C32	0.0309 (6)	0.0505 (7)	0.0303 (6)	0.0171 (5)	0.0125 (5)	0.0116 (5)
C33	0.0426 (7)	0.0432 (7)	0.0364 (7)	0.0109 (6)	−0.0042 (5)	0.0059 (5)
C34	0.0647 (10)	0.0738 (10)	0.0340 (7)	0.0399 (8)	−0.0017 (6)	0.0034 (7)
C35	0.0448 (7)	0.0451 (7)	0.0345 (7)	0.0209 (6)	0.0129 (6)	0.0074 (5)
C36	0.0519 (8)	0.0569 (8)	0.0339 (7)	0.0207 (7)	0.0083 (6)	0.0042 (6)

O1—C11	1.2148 (14)	C18—H18	0.9500
O2—C22	1.2131 (14)	C19—C20	1.3644 (18)
O3—C2	1.3617 (15)	C19—H19	0.9500
O3—C33	1.4350 (14)	C20—C21	1.4157 (18)
O4—C8	1.3650 (15)	C20—H20	0.9500
O4—C35	1.4315 (15)	C22—C23	1.5015 (16)
C1—C2	1.3901 (16)	C23—C24	1.3723 (17)
C1—C10	1.4301 (17)	C23—C32	1.4266 (16)
C1—C11	1.5093 (16)	C24—C25	1.4031 (18)
C2—C3	1.4088 (18)	C24—H24	0.9500
C3—C4	1.3576 (19)	C25—C26	1.361 (2)
C3—H3	0.9500	C25—H25	0.9500
C4—C5	1.4113 (17)	C26—C27	1.418 (2)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.4081 (18)	C27—C28	1.419 (2)
C5—C10	1.4373 (17)	C27—C32	1.4239 (18)
C6—C7	1.3621 (19)	C28—C29	1.355 (2)
C6—H6	0.9500	C28—H28	0.9500
C7—C8	1.4104 (18)	C29—C30	1.409 (2)
C7—H7	0.9500	C29—H29	0.9500
C8—C9	1.3843 (17)	C30—C31	1.3661 (19)
C9—C10	1.4319 (16)	C30—H30	0.9500
C9—C22	1.5073 (16)	C31—C32	1.4185 (19)
C11—C12	1.4994 (16)	C31—H31	0.9500
C12—C13	1.3678 (18)	C33—C34	1.496 (2)
C12—C21	1.4283 (17)	C33—H33A	0.9900
C13—C14	1.406 (2)	C33—H33B	0.9900
C13—H13	0.9500	C34—H34A	0.9800
C14—C15	1.363 (2)	C34—H34B	0.9800
C14—H14	0.9500	C34—H34C	0.9800
C15—C16	1.411 (2)	C35—C36	1.5008 (19)
C15—H15	0.9500	C35—H35A	0.9900
C16—C17	1.421 (2)	C35—H35B	0.9900
C16—C21	1.4251 (17)	C36—H36A	0.9800
C17—C18	1.356 (2)	C36—H36B	0.9800
C17—H17	0.9500	C36—H36C	0.9800
C18—C19	1.404 (2)
C2—O3—C33	119.13 (10)	C21—C20—H20	119.5
C8—O4—C35	118.97 (10)	C20—C21—C16	118.15 (12)
C2—C1—C10	119.84 (11)	C20—C21—C12	123.61 (10)
C2—C1—C11	114.61 (10)	C16—C21—C12	118.08 (11)
C10—C1—C11	125.36 (10)	O2—C22—C23	122.19 (10)
O3—C2—C1	115.41 (11)	O2—C22—C9	121.24 (10)
O3—C2—C3	122.72 (11)	C23—C22—C9	116.54 (10)
C1—C2—C3	121.84 (12)	C24—C23—C32	120.11 (11)
C4—C3—C2	119.11 (11)	C24—C23—C22	118.12 (11)
C4—C3—H3	120.4	C32—C23—C22	121.76 (11)
C2—C3—H3	120.4	C23—C24—C25	121.34 (13)
C3—C4—C5	121.73 (12)	C23—C24—H24	119.3
C3—C4—H4	119.1	C25—C24—H24	119.3
C5—C4—H4	119.1	C26—C25—C24	119.97 (13)
C6—C5—C4	119.63 (11)	C26—C25—H25	120.0
C6—C5—C10	120.35 (11)	C24—C25—H25	120.0
C4—C5—C10	120.01 (12)	C25—C26—C27	120.78 (12)
C7—C6—C5	121.85 (12)	C25—C26—H26	119.6
C7—C6—H6	119.1	C27—C26—H26	119.6
C5—C6—H6	119.1	C26—C27—C28	121.37 (13)
C6—C7—C8	118.56 (12)	C26—C27—C32	119.59 (12)
C6—C7—H7	120.7	C28—C27—C32	119.00 (14)
C8—C7—H7	120.7	C29—C28—C27	121.08 (14)
O4—C8—C9	115.18 (11)	C29—C28—H28	119.5
O4—C8—C7	122.69 (11)	C27—C28—H28	119.5
C9—C8—C7	122.11 (11)	C28—C29—C30	120.29 (13)
C8—C9—C10	120.16 (11)	C28—C29—H29	119.9
C8—C9—C22	114.25 (10)	C30—C29—H29	119.9
C10—C9—C22	125.53 (10)	C31—C30—C29	120.27 (15)
C1—C10—C9	125.67 (11)	C31—C30—H30	119.9
C1—C10—C5	117.42 (11)	C29—C30—H30	119.9
C9—C10—C5	116.91 (11)	C30—C31—C32	121.15 (14)
O1—C11—C12	121.76 (11)	C30—C31—H31	119.4
O1—C11—C1	121.13 (10)	C32—C31—H31	119.4
C12—C11—C1	117.07 (10)	C31—C32—C27	118.16 (12)
C13—C12—C21	120.45 (11)	C31—C32—C23	123.58 (11)
C13—C12—C11	117.95 (11)	C27—C32—C23	118.12 (12)
C21—C12—C11	121.60 (10)	O3—C33—C34	107.15 (11)
C12—C13—C14	120.83 (14)	O3—C33—H33A	110.3
C12—C13—H13	119.6	C34—C33—H33A	110.3
C14—C13—H13	119.6	O3—C33—H33B	110.3
C15—C14—C13	120.21 (14)	C34—C33—H33B	110.3
C15—C14—H14	119.9	H33A—C33—H33B	108.5
C13—C14—H14	119.9	C33—C34—H34A	109.5
C14—C15—C16	120.85 (12)	C33—C34—H34B	109.5
C14—C15—H15	119.6	H34A—C34—H34B	109.5
C16—C15—H15	119.6	C33—C34—H34C	109.5
C15—C16—C17	121.61 (12)	H34A—C34—H34C	109.5
C15—C16—C21	119.50 (13)	H34B—C34—H34C	109.5
C17—C16—C21	118.84 (13)	O4—C35—C36	107.01 (11)
C18—C17—C16	121.22 (12)	O4—C35—H35A	110.3
C18—C17—H17	119.4	C36—C35—H35A	110.3
C16—C17—H17	119.4	O4—C35—H35B	110.3
C17—C18—C19	119.91 (13)	C36—C35—H35B	110.3
C17—C18—H18	120.0	H35A—C35—H35B	108.6
C19—C18—H18	120.0	C35—C36—H36A	109.5
C20—C19—C18	120.76 (13)	C35—C36—H36B	109.5
C20—C19—H19	119.6	H36A—C36—H36B	109.5
C18—C19—H19	119.6	C35—C36—H36C	109.5
C19—C20—C21	121.07 (12)	H36A—C36—H36C	109.5
C19—C20—H20	119.5	H36B—C36—H36C	109.5
C33—O3—C2—C1	173.31 (10)	C14—C15—C16—C21	−2.7 (2)
C33—O3—C2—C3	−4.73 (17)	C15—C16—C17—C18	−175.60 (13)
C10—C1—C2—O3	−175.91 (10)	C21—C16—C17—C18	2.06 (19)
C11—C1—C2—O3	−0.66 (15)	C16—C17—C18—C19	−2.2 (2)
C10—C1—C2—C3	2.16 (18)	C17—C18—C19—C20	0.5 (2)
C11—C1—C2—C3	177.41 (11)	C18—C19—C20—C21	1.36 (18)
O3—C2—C3—C4	177.47 (11)	C19—C20—C21—C16	−1.48 (17)
C1—C2—C3—C4	−0.46 (19)	C19—C20—C21—C12	173.70 (11)
C2—C3—C4—C5	−0.7 (2)	C15—C16—C21—C20	177.51 (11)
C3—C4—C5—C6	−179.75 (12)	C17—C16—C21—C20	−0.20 (17)
C3—C4—C5—C10	0.06 (19)	C15—C16—C21—C12	2.06 (17)
C4—C5—C6—C7	−179.93 (12)	C17—C16—C21—C12	−175.65 (10)
C10—C5—C6—C7	0.3 (2)	C13—C12—C21—C20	−174.76 (12)
C5—C6—C7—C8	−0.7 (2)	C11—C12—C21—C20	5.09 (17)
C35—O4—C8—C9	−177.76 (10)	C13—C12—C21—C16	0.42 (16)
C35—O4—C8—C7	3.98 (18)	C11—C12—C21—C16	−179.73 (10)
C6—C7—C8—O4	177.47 (12)	C8—C9—C22—O2	−111.50 (13)
C6—C7—C8—C9	−0.7 (2)	C10—C9—C22—O2	65.60 (17)
O4—C8—C9—C10	−175.82 (10)	C8—C9—C22—C23	66.74 (14)
C7—C8—C9—C10	2.45 (19)	C10—C9—C22—C23	−116.16 (12)
O4—C8—C9—C22	1.45 (16)	O2—C22—C23—C24	−132.46 (12)
C7—C8—C9—C22	179.73 (11)	C9—C22—C23—C24	49.32 (15)
C2—C1—C10—C9	177.29 (11)	O2—C22—C23—C32	46.38 (17)
C11—C1—C10—C9	2.59 (18)	C9—C22—C23—C32	−131.84 (11)
C2—C1—C10—C5	−2.66 (17)	C32—C23—C24—C25	−3.29 (18)
C11—C1—C10—C5	−177.36 (10)	C22—C23—C24—C25	175.57 (12)
C8—C9—C10—C1	177.30 (11)	C23—C24—C25—C26	1.5 (2)
C22—C9—C10—C1	0.36 (19)	C24—C25—C26—C27	1.4 (2)
C8—C9—C10—C5	−2.76 (17)	C25—C26—C27—C28	175.37 (13)
C22—C9—C10—C5	−179.70 (10)	C25—C26—C27—C32	−2.4 (2)
C6—C5—C10—C1	−178.61 (11)	C26—C27—C28—C29	−175.54 (13)
C4—C5—C10—C1	1.59 (17)	C32—C27—C28—C29	2.3 (2)
C6—C5—C10—C9	1.45 (17)	C27—C28—C29—C30	−1.3 (2)
C4—C5—C10—C9	−178.35 (11)	C28—C29—C30—C31	−0.7 (2)
C2—C1—C11—O1	−114.04 (12)	C29—C30—C31—C32	1.7 (2)
C10—C1—C11—O1	60.90 (16)	C30—C31—C32—C27	−0.59 (18)
C2—C1—C11—C12	64.06 (14)	C30—C31—C32—C23	175.03 (11)
C10—C1—C11—C12	−121.00 (12)	C26—C27—C32—C31	176.52 (12)
O1—C11—C12—C13	−132.64 (13)	C28—C27—C32—C31	−1.34 (17)
C1—C11—C12—C13	49.27 (15)	C26—C27—C32—C23	0.66 (18)
O1—C11—C12—C21	47.51 (16)	C28—C27—C32—C23	−177.21 (11)
C1—C11—C12—C21	−130.58 (11)	C24—C23—C32—C31	−173.48 (12)
C21—C12—C13—C14	−2.40 (19)	C22—C23—C32—C31	7.71 (17)
C11—C12—C13—C14	177.75 (12)	C24—C23—C32—C27	2.15 (17)
C12—C13—C14—C15	1.9 (2)	C22—C23—C32—C27	−176.67 (11)
C13—C14—C15—C16	0.7 (2)	C2—O3—C33—C34	179.03 (11)
C14—C15—C16—C17	175.00 (14)	C8—O4—C35—C36	177.51 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···Cg4i	0.95	2.77	3.5662 (15)	142
C7—H7···Cg6i	0.95	2.76	3.5662 (16)	143
C30—H30···O2ii	0.95	2.53	3.3289 (19)	142
C34—H34A···O1iii	0.98	2.47	3.423 (2)	163
C35—H35B···O2iv	0.99	2.59	3.5476 (17)	163

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 and Cg6 are the centroids of the C16–C21 and C27–C32 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯Cg4i	0.95	2.77	3.5662 (15)	142
C7—H7⋯Cg6i	0.95	2.76	3.5662 (16)	143
C30—H30⋯O2ii	0.95	2.53	3.3289 (19)	142
C34—H34A⋯O1iii	0.98	2.47	3.423 (2)	163
C35—H35B⋯O2iv	0.99	2.59	3.5476 (17)	163

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