{2,7-Dimeth-oxy-8-[4-(2-methyl-prop-yl)benzo-yl]naphthalen-1-yl}[4-(2-methyl-prop-yl)phen-yl]methanone.

In the mol-ecule of the title compound, C34H36O4, the two 4-isobutyl-benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel, and the benzene rings make a dihedral angle of 21.59 (7)°. The dihedral angles between the benzene rings and the naphthalene ring system are 69.26 (6) and 64.29 (5)°. There are no classical hydrogen bonds in the structure, but inversion-related mol-ecules engage in π-π stacking, with an inter-planar spacing between related naphthalene groups of 3.4120 (16) Å.

Related literature

For details of the formation reaction of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Hijikata et al. (2010 ▶); Muto et al. (2010 ▶); Sasagawa, Hijikata et al. (2011 ▶); Sasagawa, Muto et al. (2011 ▶); Sasagawa et al. (2012 ▶).

Experimental

Crystal data

C34H36O4

M = 508.63

Monoclinic,

a = 18.5280 (4) Å

b = 7.83885 (15) Å

c = 20.2304 (4) Å

β = 103.642 (1)°

V = 2855.33 (10) Å3

Z = 4

Cu Kα radiation

μ = 0.60 mm−1

T = 193 K

0.60 × 0.40 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.714, T max = 0.971

50913 measured reflections

5237 independent reflections

3838 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.126

S = 1.12

5237 reflections

350 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.15 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: PROCESS-AUTO; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); 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/S1600536812045953/pk2455sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812045953/pk2455Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812045953/pk2455Isup3.cml

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

C34H36O4	F(000) = 1088
Mr = 508.63	Dx = 1.183 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ybc	Cell parameters from 26694 reflections
a = 18.5280 (4) Å	θ = 3.7–68.3°
b = 7.83885 (15) Å	µ = 0.60 mm−1
c = 20.2304 (4) Å	T = 193 K
β = 103.642 (1)°	Platelet, colorless
V = 2855.33 (10) Å3	0.60 × 0.40 × 0.05 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	5237 independent reflections
Radiation source: fine-focus sealed tube	3838 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.052
ω scans	θmax = 68.2°, θmin = 4.5°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −21→22
Tmin = 0.714, Tmax = 0.971	k = −9→9
50913 measured reflections	l = −24→24

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)] = 0.042	H-atom parameters constrained
wR(F2) = 0.126	w = 1/[σ2(Fo2) + (0.0662P)2] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
5237 reflections	Δρmax = 0.17 e Å−3
350 parameters	Δρmin = −0.15 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: 0.0022 (2)

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	0.66145 (6)	0.32112 (15)	0.61940 (5)	0.0635 (3)
O2	0.53292 (5)	0.00068 (13)	0.27977 (5)	0.0576 (3)
O3	0.71658 (5)	0.02470 (13)	0.51300 (5)	0.0553 (3)
O4	0.67422 (5)	0.26567 (12)	0.36980 (5)	0.0527 (3)
C1	0.62041 (8)	0.22224 (18)	0.50872 (7)	0.0453 (3)
C2	0.60247 (8)	0.29086 (19)	0.56568 (7)	0.0509 (4)
C3	0.52803 (9)	0.3152 (2)	0.56905 (8)	0.0565 (4)
H3	0.5168	0.3669	0.6079	0.068*
C4	0.47275 (9)	0.26432 (19)	0.51642 (8)	0.0555 (4)
H4	0.4227	0.2778	0.5195	0.067*
C5	0.42902 (8)	0.13689 (19)	0.40346 (8)	0.0537 (4)
H5	0.3793	0.1477	0.4078	0.064*
C6	0.44203 (8)	0.0687 (2)	0.34550 (8)	0.0547 (4)
H6	0.4019	0.0305	0.3102	0.066*
C7	0.51556 (8)	0.05545 (18)	0.33848 (7)	0.0478 (4)
C8	0.57515 (7)	0.10547 (17)	0.38983 (6)	0.0434 (3)
C9	0.56242 (7)	0.17307 (17)	0.45187 (6)	0.0440 (3)
C10	0.48732 (8)	0.19171 (18)	0.45706 (7)	0.0478 (4)
C11	0.70027 (8)	0.1766 (2)	0.51402 (6)	0.0469 (4)
C12	0.65026 (7)	0.12146 (18)	0.37335 (6)	0.0428 (3)
C13	0.75748 (8)	0.3109 (2)	0.52059 (6)	0.0481 (4)
C14	0.73950 (9)	0.4833 (2)	0.51447 (7)	0.0545 (4)
H14	0.6890	0.5170	0.5068	0.065*
C15	0.79377 (9)	0.6062 (2)	0.51933 (8)	0.0600 (4)
H15	0.7802	0.7233	0.5149	0.072*
C16	0.86786 (9)	0.5603 (2)	0.53064 (8)	0.0638 (4)
C17	0.88575 (9)	0.3888 (3)	0.53645 (10)	0.0737 (5)
H17	0.9363	0.3555	0.5441	0.088*
C18	0.83170 (9)	0.2650 (2)	0.53138 (8)	0.0641 (4)
H18	0.8454	0.1479	0.5353	0.077*
C19	0.69369 (8)	−0.02869 (17)	0.36131 (6)	0.0422 (3)
C20	0.66833 (8)	−0.19549 (18)	0.36293 (6)	0.0465 (4)
H20	0.6214	−0.2158	0.3729	0.056*
C21	0.71025 (8)	−0.33134 (19)	0.35037 (7)	0.0498 (4)
H21	0.6919	−0.4441	0.3518	0.060*
C22	0.77954 (8)	−0.30609 (19)	0.33551 (7)	0.0486 (4)
C23	0.80510 (8)	−0.1394 (2)	0.33565 (8)	0.0550 (4)
H23	0.8524	−0.1189	0.3267	0.066*
C24	0.76339 (8)	−0.00324 (19)	0.34854 (7)	0.0515 (4)
H24	0.7825	0.1093	0.3487	0.062*
C25	0.65039 (10)	0.4214 (2)	0.67461 (8)	0.0731 (5)
H25A	0.6249	0.5275	0.6572	0.088*
H25B	0.6986	0.4483	0.7050	0.088*
H25C	0.6200	0.3577	0.6998	0.088*
C26	0.47399 (9)	−0.0512 (2)	0.22480 (7)	0.0619 (4)
H26A	0.4946	−0.0948	0.1877	0.074*
H26B	0.4417	0.0466	0.2086	0.074*
H26C	0.4451	−0.1412	0.2402	0.074*
C27	0.92724 (10)	0.6961 (3)	0.53805 (11)	0.0823 (6)
H27A	0.9138	0.7750	0.4989	0.099*
H27B	0.9748	0.6408	0.5364	0.099*
C28	0.93864 (10)	0.7998 (3)	0.60370 (11)	0.0817 (6)
H28	0.8907	0.8588	0.6035	0.098*
C29	0.99748 (11)	0.9370 (3)	0.60563 (15)	0.1205 (9)
H29A	1.0451	0.8829	0.6053	0.145*
H29B	1.0028	1.0053	0.6471	0.145*
H29C	0.9824	1.0111	0.5657	0.145*
C30	0.95729 (12)	0.6876 (3)	0.66594 (12)	0.1083 (8)
H30A	0.9650	0.7586	0.7069	0.130*
H30B	1.0027	0.6232	0.6663	0.130*
H30C	0.9163	0.6081	0.6652	0.130*
C31	0.82253 (8)	−0.4543 (2)	0.31722 (7)	0.0565 (4)
H31A	0.8271	−0.5429	0.3528	0.068*
H31B	0.8732	−0.4154	0.3168	0.068*
C32	0.78695 (9)	−0.5339 (2)	0.24818 (8)	0.0579 (4)
H32	0.7387	−0.5866	0.2514	0.069*
C33	0.77059 (10)	−0.4010 (3)	0.19229 (8)	0.0755 (5)
H33A	0.7348	−0.3180	0.2019	0.091*
H33B	0.7497	−0.4567	0.1486	0.091*
H33C	0.8167	−0.3422	0.1902	0.091*
C34	0.83574 (9)	−0.6740 (2)	0.23036 (9)	0.0711 (5)
H34A	0.8819	−0.6240	0.2235	0.085*
H34B	0.8095	−0.7311	0.1885	0.085*
H34C	0.8473	−0.7571	0.2675	0.085*

	U11	U22	U33	U12	U13	U23
O1	0.0687 (7)	0.0842 (8)	0.0372 (5)	0.0057 (6)	0.0118 (5)	−0.0101 (5)
O2	0.0578 (6)	0.0690 (8)	0.0419 (5)	−0.0008 (5)	0.0037 (4)	−0.0095 (5)
O3	0.0656 (7)	0.0522 (7)	0.0466 (6)	0.0076 (5)	0.0103 (5)	0.0012 (5)
O4	0.0626 (6)	0.0452 (6)	0.0515 (6)	−0.0059 (5)	0.0161 (5)	0.0028 (5)
C1	0.0543 (8)	0.0444 (9)	0.0385 (7)	0.0016 (6)	0.0132 (6)	0.0038 (6)
C2	0.0615 (9)	0.0520 (9)	0.0402 (7)	0.0029 (7)	0.0144 (7)	0.0031 (6)
C3	0.0670 (10)	0.0617 (10)	0.0456 (8)	0.0080 (8)	0.0229 (7)	0.0026 (7)
C4	0.0595 (9)	0.0571 (10)	0.0549 (9)	0.0059 (7)	0.0238 (7)	0.0094 (7)
C5	0.0483 (8)	0.0528 (10)	0.0607 (9)	−0.0002 (7)	0.0139 (7)	0.0073 (7)
C6	0.0525 (9)	0.0526 (10)	0.0552 (9)	−0.0028 (7)	0.0049 (7)	−0.0003 (7)
C7	0.0523 (8)	0.0459 (9)	0.0436 (8)	−0.0006 (7)	0.0082 (6)	0.0009 (6)
C8	0.0505 (8)	0.0394 (8)	0.0399 (7)	0.0011 (6)	0.0098 (6)	0.0043 (6)
C9	0.0520 (8)	0.0402 (8)	0.0405 (7)	0.0011 (6)	0.0120 (6)	0.0064 (6)
C10	0.0525 (8)	0.0447 (9)	0.0484 (8)	0.0018 (7)	0.0165 (7)	0.0079 (6)
C11	0.0587 (9)	0.0518 (10)	0.0294 (6)	0.0052 (7)	0.0090 (6)	0.0023 (6)
C12	0.0529 (8)	0.0437 (9)	0.0304 (6)	−0.0037 (7)	0.0072 (6)	0.0026 (6)
C13	0.0525 (9)	0.0558 (10)	0.0358 (7)	0.0014 (7)	0.0099 (6)	−0.0001 (6)
C14	0.0521 (9)	0.0589 (11)	0.0492 (8)	0.0019 (7)	0.0056 (7)	0.0025 (7)
C15	0.0640 (10)	0.0599 (11)	0.0540 (9)	−0.0040 (8)	0.0094 (7)	0.0004 (8)
C16	0.0617 (10)	0.0731 (12)	0.0600 (10)	−0.0103 (9)	0.0213 (8)	−0.0056 (8)
C17	0.0517 (10)	0.0813 (14)	0.0927 (13)	0.0007 (9)	0.0260 (9)	−0.0087 (11)
C18	0.0587 (10)	0.0632 (11)	0.0731 (11)	0.0066 (8)	0.0207 (8)	−0.0032 (9)
C19	0.0499 (8)	0.0452 (9)	0.0311 (6)	−0.0029 (6)	0.0088 (6)	0.0016 (6)
C20	0.0533 (8)	0.0480 (9)	0.0401 (7)	−0.0033 (7)	0.0149 (6)	0.0020 (6)
C21	0.0593 (9)	0.0467 (9)	0.0450 (8)	−0.0014 (7)	0.0157 (7)	0.0011 (6)
C22	0.0532 (9)	0.0534 (10)	0.0366 (7)	0.0029 (7)	0.0055 (6)	−0.0010 (6)
C23	0.0484 (8)	0.0610 (10)	0.0569 (9)	−0.0039 (7)	0.0155 (7)	−0.0073 (7)
C24	0.0524 (9)	0.0503 (9)	0.0523 (8)	−0.0067 (7)	0.0134 (7)	−0.0032 (7)
C25	0.0917 (13)	0.0783 (12)	0.0477 (9)	0.0079 (10)	0.0132 (8)	−0.0148 (9)
C26	0.0693 (10)	0.0641 (11)	0.0460 (8)	−0.0106 (8)	0.0011 (7)	−0.0051 (7)
C27	0.0692 (12)	0.0886 (15)	0.0965 (14)	−0.0146 (10)	0.0342 (10)	−0.0076 (11)
C28	0.0573 (11)	0.0841 (14)	0.1007 (15)	−0.0095 (10)	0.0126 (10)	−0.0137 (12)
C29	0.0759 (14)	0.1112 (19)	0.173 (3)	−0.0314 (13)	0.0276 (15)	−0.0368 (18)
C30	0.0873 (15)	0.125 (2)	0.0978 (17)	0.0013 (14)	−0.0075 (12)	−0.0127 (15)
C31	0.0556 (9)	0.0624 (10)	0.0497 (8)	0.0084 (8)	0.0089 (7)	−0.0037 (7)
C32	0.0522 (9)	0.0668 (11)	0.0553 (9)	0.0009 (8)	0.0141 (7)	−0.0109 (8)
C33	0.0761 (12)	0.1001 (15)	0.0466 (9)	0.0150 (11)	0.0072 (8)	−0.0064 (9)
C34	0.0699 (11)	0.0795 (13)	0.0663 (11)	0.0052 (9)	0.0208 (9)	−0.0192 (9)

O1—C2	1.3679 (17)	C20—H20	0.9500
O1—C25	1.4198 (17)	C21—C22	1.4000 (19)
O2—C7	1.3707 (16)	C21—H21	0.9500
O2—C26	1.4218 (16)	C22—C23	1.389 (2)
O3—C11	1.2297 (16)	C22—C31	1.5034 (19)
O4—C12	1.2227 (15)	C23—C24	1.3786 (19)
C1—C2	1.3814 (18)	C23—H23	0.9500
C1—C9	1.4292 (19)	C24—H24	0.9500
C1—C11	1.502 (2)	C25—H25A	0.9800
C2—C3	1.410 (2)	C25—H25B	0.9800
C3—C4	1.352 (2)	C25—H25C	0.9800
C3—H3	0.9500	C26—H26A	0.9800
C4—C10	1.4113 (19)	C26—H26B	0.9800
C4—H4	0.9500	C26—H26C	0.9800
C5—C6	1.361 (2)	C27—C28	1.528 (3)
C5—C10	1.4053 (19)	C27—H27A	0.9900
C5—H5	0.9500	C27—H27B	0.9900
C6—C7	1.406 (2)	C28—C30	1.508 (3)
C6—H6	0.9500	C28—C29	1.526 (3)
C7—C8	1.3823 (18)	C28—H28	1.0000
C8—C9	1.4322 (18)	C29—H29A	0.9800
C8—C12	1.5107 (18)	C29—H29B	0.9800
C9—C10	1.4274 (18)	C29—H29C	0.9800
C11—C13	1.478 (2)	C30—H30A	0.9800
C12—C19	1.4781 (18)	C30—H30B	0.9800
C13—C18	1.388 (2)	C30—H30C	0.9800
C13—C14	1.391 (2)	C31—C32	1.530 (2)
C14—C15	1.379 (2)	C31—H31A	0.9900
C14—H14	0.9500	C31—H31B	0.9900
C15—C16	1.385 (2)	C32—C33	1.515 (2)
C15—H15	0.9500	C32—C34	1.519 (2)
C16—C17	1.383 (3)	C32—H32	1.0000
C16—C27	1.513 (2)	C33—H33A	0.9800
C17—C18	1.381 (2)	C33—H33B	0.9800
C17—H17	0.9500	C33—H33C	0.9800
C18—H18	0.9500	C34—H34A	0.9800
C19—C24	1.3898 (19)	C34—H34B	0.9800
C19—C20	1.3923 (18)	C34—H34C	0.9800
C20—C21	1.3765 (18)
C2—O1—C25	118.99 (12)	C21—C22—C31	120.63 (13)
C7—O2—C26	118.26 (11)	C24—C23—C22	121.51 (14)
C2—C1—C9	119.55 (13)	C24—C23—H23	119.2
C2—C1—C11	117.40 (12)	C22—C23—H23	119.2
C9—C1—C11	122.30 (12)	C23—C24—C19	120.72 (14)
O1—C2—C1	115.22 (13)	C23—C24—H24	119.6
O1—C2—C3	123.04 (13)	C19—C24—H24	119.6
C1—C2—C3	121.58 (13)	O1—C25—H25A	109.5
C4—C3—C2	119.34 (14)	O1—C25—H25B	109.5
C4—C3—H3	120.3	H25A—C25—H25B	109.5
C2—C3—H3	120.3	O1—C25—H25C	109.5
C3—C4—C10	121.85 (14)	H25A—C25—H25C	109.5
C3—C4—H4	119.1	H25B—C25—H25C	109.5
C10—C4—H4	119.1	O2—C26—H26A	109.5
C6—C5—C10	121.66 (13)	O2—C26—H26B	109.5
C6—C5—H5	119.2	H26A—C26—H26B	109.5
C10—C5—H5	119.2	O2—C26—H26C	109.5
C5—C6—C7	119.25 (14)	H26A—C26—H26C	109.5
C5—C6—H6	120.4	H26B—C26—H26C	109.5
C7—C6—H6	120.4	C16—C27—C28	114.11 (15)
O2—C7—C8	115.53 (12)	C16—C27—H27A	108.7
O2—C7—C6	122.79 (13)	C28—C27—H27A	108.7
C8—C7—C6	121.61 (13)	C16—C27—H27B	108.7
C7—C8—C9	119.74 (12)	C28—C27—H27B	108.7
C7—C8—C12	118.15 (12)	H27A—C27—H27B	107.6
C9—C8—C12	120.88 (12)	C30—C28—C29	111.62 (19)
C10—C9—C1	118.29 (12)	C30—C28—C27	111.91 (18)
C10—C9—C8	117.86 (12)	C29—C28—C27	110.40 (18)
C1—C9—C8	123.85 (12)	C30—C28—H28	107.6
C5—C10—C4	120.89 (13)	C29—C28—H28	107.6
C5—C10—C9	119.80 (13)	C27—C28—H28	107.6
C4—C10—C9	119.30 (13)	C28—C29—H29A	109.5
O3—C11—C13	121.17 (13)	C28—C29—H29B	109.5
O3—C11—C1	118.13 (14)	H29A—C29—H29B	109.5
C13—C11—C1	120.70 (13)	C28—C29—H29C	109.5
O4—C12—C19	120.49 (12)	H29A—C29—H29C	109.5
O4—C12—C8	117.11 (12)	H29B—C29—H29C	109.5
C19—C12—C8	122.40 (12)	C28—C30—H30A	109.5
C18—C13—C14	118.28 (15)	C28—C30—H30B	109.5
C18—C13—C11	119.50 (14)	H30A—C30—H30B	109.5
C14—C13—C11	122.19 (13)	C28—C30—H30C	109.5
C15—C14—C13	121.14 (15)	H30A—C30—H30C	109.5
C15—C14—H14	119.4	H30B—C30—H30C	109.5
C13—C14—H14	119.4	C22—C31—C32	113.63 (12)
C14—C15—C16	120.51 (16)	C22—C31—H31A	108.8
C14—C15—H15	119.7	C32—C31—H31A	108.8
C16—C15—H15	119.7	C22—C31—H31B	108.8
C17—C16—C15	118.37 (16)	C32—C31—H31B	108.8
C17—C16—C27	121.43 (16)	H31A—C31—H31B	107.7
C15—C16—C27	120.19 (17)	C33—C32—C34	110.21 (13)
C18—C17—C16	121.46 (16)	C33—C32—C31	111.58 (14)
C18—C17—H17	119.3	C34—C32—C31	111.05 (13)
C16—C17—H17	119.3	C33—C32—H32	107.9
C17—C18—C13	120.23 (16)	C34—C32—H32	107.9
C17—C18—H18	119.9	C31—C32—H32	107.9
C13—C18—H18	119.9	C32—C33—H33A	109.5
C24—C19—C20	118.21 (13)	C32—C33—H33B	109.5
C24—C19—C12	118.82 (12)	H33A—C33—H33B	109.5
C20—C19—C12	122.96 (12)	C32—C33—H33C	109.5
C21—C20—C19	120.92 (13)	H33A—C33—H33C	109.5
C21—C20—H20	119.5	H33B—C33—H33C	109.5
C19—C20—H20	119.5	C32—C34—H34A	109.5
C20—C21—C22	121.07 (13)	C32—C34—H34B	109.5
C20—C21—H21	119.5	H34A—C34—H34B	109.5
C22—C21—H21	119.5	C32—C34—H34C	109.5
C23—C22—C21	117.51 (13)	H34A—C34—H34C	109.5
C23—C22—C31	121.81 (13)	H34B—C34—H34C	109.5
C25—O1—C2—C1	167.69 (14)	C9—C8—C12—O4	−59.53 (17)
C25—O1—C2—C3	−16.9 (2)	C7—C8—C12—C19	−71.74 (16)
C9—C1—C2—O1	174.96 (12)	C9—C8—C12—C19	120.94 (14)
C11—C1—C2—O1	4.7 (2)	O3—C11—C13—C18	−5.3 (2)
C9—C1—C2—C3	−0.6 (2)	C1—C11—C13—C18	174.38 (13)
C11—C1—C2—C3	−170.86 (13)	O3—C11—C13—C14	172.88 (13)
O1—C2—C3—C4	−172.57 (14)	C1—C11—C13—C14	−7.42 (19)
C1—C2—C3—C4	2.6 (2)	C18—C13—C14—C15	−0.3 (2)
C2—C3—C4—C10	−1.9 (2)	C11—C13—C14—C15	−178.56 (12)
C10—C5—C6—C7	−1.1 (2)	C13—C14—C15—C16	−0.2 (2)
C26—O2—C7—C8	−179.50 (13)	C14—C15—C16—C17	0.4 (2)
C26—O2—C7—C6	−2.6 (2)	C14—C15—C16—C27	−178.11 (15)
C5—C6—C7—O2	−174.82 (14)	C15—C16—C17—C18	−0.2 (3)
C5—C6—C7—C8	1.9 (2)	C27—C16—C17—C18	178.35 (16)
O2—C7—C8—C9	176.77 (12)	C16—C17—C18—C13	−0.4 (3)
C6—C7—C8—C9	−0.2 (2)	C14—C13—C18—C17	0.6 (2)
O2—C7—C8—C12	9.30 (19)	C11—C13—C18—C17	178.87 (14)
C6—C7—C8—C12	−167.63 (13)	O4—C12—C19—C24	2.49 (18)
C2—C1—C9—C10	−2.1 (2)	C8—C12—C19—C24	−178.00 (12)
C11—C1—C9—C10	167.73 (12)	O4—C12—C19—C20	−178.28 (12)
C2—C1—C9—C8	178.13 (13)	C8—C12—C19—C20	1.24 (18)
C11—C1—C9—C8	−12.1 (2)	C24—C19—C20—C21	−1.77 (19)
C7—C8—C9—C10	−2.21 (19)	C12—C19—C20—C21	178.99 (12)
C12—C8—C9—C10	164.91 (12)	C19—C20—C21—C22	−0.1 (2)
C7—C8—C9—C1	177.60 (13)	C20—C21—C22—C23	1.6 (2)
C12—C8—C9—C1	−15.3 (2)	C20—C21—C22—C31	−175.83 (12)
C6—C5—C10—C4	179.11 (14)	C21—C22—C23—C24	−1.3 (2)
C6—C5—C10—C9	−1.3 (2)	C31—C22—C23—C24	176.11 (13)
C3—C4—C10—C5	178.87 (14)	C22—C23—C24—C19	−0.5 (2)
C3—C4—C10—C9	−0.7 (2)	C20—C19—C24—C23	2.1 (2)
C1—C9—C10—C5	−176.89 (12)	C12—C19—C24—C23	−178.65 (12)
C8—C9—C10—C5	2.9 (2)	C17—C16—C27—C28	−108.6 (2)
C1—C9—C10—C4	2.7 (2)	C15—C16—C27—C28	69.9 (2)
C8—C9—C10—C4	−177.46 (12)	C16—C27—C28—C30	56.9 (2)
C2—C1—C11—O3	111.13 (15)	C16—C27—C28—C29	−178.08 (17)
C9—C1—C11—O3	−58.87 (18)	C23—C22—C31—C32	−108.55 (16)
C2—C1—C11—C13	−68.58 (17)	C21—C22—C31—C32	68.78 (18)
C9—C1—C11—C13	121.42 (15)	C22—C31—C32—C33	52.40 (18)
C7—C8—C12—O4	107.79 (15)	C22—C31—C32—C34	175.80 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O4i	0.95	2.34	3.2716 (18)	167