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

In the title compound, C36H28O4, the two 2-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 48.35 (5)°. The dihedral angles between the central 2,7-dieth-oxy-naphthalene ring system and the terminal naphthalene ring systems are 77.64 (4) and 73.73 (4)°. In the crystal, mol-ecules are linked into chains along the a-axis direction by dual C-H⋯O inter-actions between naphthoyl groups.

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 ▶); Sasagawa et al. (2012 ▶); Isogai et al. (2013 ▶); Yoshiwaka et al. (2013 ▶).

Experimental

Crystal data

C36H28O4

M = 524.58

Monoclinic,

a = 7.86946 (14) Å

b = 27.1458 (5) Å

c = 12.8490 (2) Å

β = 102.267 (1)°

V = 2682.16 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.67 mm−1

T = 193 K

0.50 × 0.25 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.732, T max = 0.878

41696 measured reflections

4914 independent reflections

3996 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.097

S = 1.09

4914 reflections

364 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.15 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku, 2010 ▶); 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/S1600536813003577/rz5043sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813003577/rz5043Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813003577/rz5043Isup3.cml

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

C36H28O4	F(000) = 1104
Mr = 524.58	Dx = 1.299 Mg m−3
Monoclinic, P21/c	Melting point = 493.0–494.5 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.54187 Å
a = 7.86946 (14) Å	Cell parameters from 33371 reflections
b = 27.1458 (5) Å	θ = 3.3–68.2°
c = 12.8490 (2) Å	µ = 0.67 mm−1
β = 102.267 (1)°	T = 193 K
V = 2682.16 (8) Å3	Block, colourless
Z = 4	0.50 × 0.25 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	4914 independent reflections
Radiation source: rotating anode	3996 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −31→32
Tmin = 0.732, Tmax = 0.878	l = −15→15
41696 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)] = 0.036	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.0448P)2 + 0.4544P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
4914 reflections	Δρmax = 0.20 e Å−3
364 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: 0.00121 (13)

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	0.07897 (13)	0.25900 (3)	0.51894 (8)	0.0457 (3)
O2	0.55755 (13)	0.32784 (3)	1.03877 (7)	0.0436 (2)
O3	0.39273 (11)	0.34984 (3)	0.63817 (7)	0.0400 (2)
O4	0.21986 (11)	0.37405 (3)	0.83968 (8)	0.0431 (2)
C1	0.24047 (16)	0.28182 (5)	0.68544 (10)	0.0338 (3)
C2	0.16047 (17)	0.24468 (5)	0.61849 (10)	0.0365 (3)
C3	0.17099 (18)	0.19490 (5)	0.65104 (11)	0.0403 (3)
H3	0.1137	0.1700	0.6047	0.048*
C4	0.26404 (18)	0.18312 (5)	0.74950 (11)	0.0400 (3)
H4	0.2736	0.1495	0.7705	0.048*
C5	0.44227 (18)	0.20619 (5)	0.92342 (11)	0.0402 (3)
H5	0.4541	0.1723	0.9422	0.048*
C6	0.51793 (18)	0.24052 (5)	0.99566 (11)	0.0401 (3)
H6	0.5833	0.2308	1.0634	0.048*
C7	0.49772 (17)	0.29080 (5)	0.96834 (10)	0.0360 (3)
C8	0.40829 (16)	0.30593 (5)	0.86876 (10)	0.0334 (3)
C9	0.33228 (16)	0.26999 (5)	0.79099 (10)	0.0334 (3)
C10	0.34690 (16)	0.21927 (5)	0.82158 (10)	0.0358 (3)
C11	0.24972 (17)	0.33218 (5)	0.63750 (10)	0.0339 (3)
C12	0.37086 (16)	0.36012 (5)	0.85329 (10)	0.0336 (3)
C13	0.08776 (17)	0.35910 (5)	0.58868 (10)	0.0357 (3)
C14	0.09312 (19)	0.39523 (5)	0.51522 (11)	0.0410 (3)
H14	0.1997	0.4019	0.4944	0.049*
C15	−0.0564 (2)	0.42290 (5)	0.46955 (11)	0.0443 (3)
C16	−0.0535 (2)	0.46069 (6)	0.39398 (13)	0.0585 (4)
H16	0.0507	0.4672	0.3703	0.070*
C17	−0.1985 (3)	0.48786 (7)	0.35494 (14)	0.0710 (5)
H17	−0.1945	0.5133	0.3047	0.085*
C18	−0.3539 (3)	0.47841 (7)	0.38869 (14)	0.0735 (6)
H18	−0.4544	0.4975	0.3608	0.088*
C19	−0.3623 (2)	0.44224 (7)	0.46071 (13)	0.0624 (5)
H19	−0.4684	0.4363	0.4826	0.075*
C20	−0.21336 (19)	0.41325 (6)	0.50351 (12)	0.0473 (4)
C21	−0.21620 (19)	0.37583 (6)	0.57927 (12)	0.0485 (4)
H21	−0.3209	0.3692	0.6023	0.058*
C22	−0.07049 (18)	0.34901 (5)	0.62000 (11)	0.0421 (3)
H22	−0.0754	0.3234	0.6697	0.051*
C23	0.51548 (16)	0.39574 (5)	0.85724 (10)	0.0331 (3)
C24	0.68331 (17)	0.37994 (5)	0.84828 (11)	0.0406 (3)
H24	0.7053	0.3458	0.8409	0.049*
C25	0.81350 (19)	0.41323 (6)	0.85009 (12)	0.0483 (4)
H25	0.9250	0.4021	0.8431	0.058*
C26	0.78459 (18)	0.46415 (5)	0.86224 (11)	0.0442 (3)
C27	0.9164 (2)	0.50030 (7)	0.86551 (15)	0.0625 (5)
H27	1.0286	0.4907	0.8569	0.075*
C28	0.8826 (3)	0.54880 (7)	0.88092 (15)	0.0691 (5)
H28	0.9722	0.5725	0.8831	0.083*
C29	0.7192 (3)	0.56425 (6)	0.89353 (14)	0.0619 (5)
H29	0.6988	0.5981	0.9055	0.074*
C30	0.5895 (2)	0.53092 (5)	0.88874 (12)	0.0506 (4)
H30	0.4778	0.5418	0.8961	0.061*
C31	0.61786 (18)	0.48013 (5)	0.87293 (10)	0.0396 (3)
C32	0.48516 (17)	0.44475 (5)	0.86871 (10)	0.0367 (3)
H32	0.3722	0.4553	0.8740	0.044*
C33	−0.01793 (18)	0.22392 (5)	0.44723 (11)	0.0400 (3)
H33A	−0.1017	0.2063	0.4814	0.048*
H33B	0.0609	0.1995	0.4252	0.048*
C34	−0.11200 (19)	0.25281 (5)	0.35288 (11)	0.0445 (3)
H34A	−0.0272	0.2694	0.3190	0.053*
H34B	−0.1868	0.2775	0.3764	0.053*
H34C	−0.1835	0.2305	0.3016	0.053*
C35	0.65820 (18)	0.31522 (5)	1.14207 (10)	0.0419 (3)
H35A	0.7612	0.2956	1.1352	0.050*
H35B	0.5874	0.2956	1.1821	0.050*
C36	0.7138 (2)	0.36274 (6)	1.19899 (13)	0.0588 (4)
H36A	0.7934	0.3558	1.2671	0.071*
H36B	0.6113	0.3802	1.2121	0.071*
H36C	0.7729	0.3833	1.1550	0.071*

	U11	U22	U33	U12	U13	U23
O1	0.0550 (6)	0.0357 (5)	0.0401 (5)	−0.0040 (4)	−0.0040 (4)	−0.0021 (4)
O2	0.0533 (6)	0.0400 (5)	0.0338 (5)	−0.0012 (4)	0.0010 (4)	0.0004 (4)
O3	0.0368 (5)	0.0424 (5)	0.0414 (5)	−0.0046 (4)	0.0097 (4)	0.0002 (4)
O4	0.0330 (5)	0.0413 (5)	0.0545 (6)	0.0036 (4)	0.0084 (4)	−0.0037 (4)
C1	0.0329 (7)	0.0317 (7)	0.0369 (7)	0.0008 (5)	0.0080 (5)	0.0001 (5)
C2	0.0353 (7)	0.0371 (7)	0.0366 (7)	0.0010 (6)	0.0064 (6)	0.0002 (6)
C3	0.0423 (8)	0.0327 (7)	0.0450 (8)	−0.0016 (6)	0.0073 (6)	−0.0052 (6)
C4	0.0444 (8)	0.0303 (7)	0.0464 (8)	0.0019 (6)	0.0121 (6)	0.0018 (6)
C5	0.0442 (8)	0.0353 (7)	0.0421 (7)	0.0036 (6)	0.0116 (6)	0.0070 (6)
C6	0.0423 (8)	0.0409 (8)	0.0364 (7)	0.0020 (6)	0.0070 (6)	0.0057 (6)
C7	0.0353 (7)	0.0365 (7)	0.0369 (7)	−0.0010 (5)	0.0093 (6)	−0.0004 (6)
C8	0.0314 (7)	0.0341 (7)	0.0359 (7)	0.0003 (5)	0.0096 (5)	0.0006 (5)
C9	0.0306 (7)	0.0333 (7)	0.0379 (7)	0.0016 (5)	0.0106 (5)	0.0007 (5)
C10	0.0363 (7)	0.0329 (7)	0.0403 (7)	0.0018 (5)	0.0129 (6)	0.0008 (6)
C11	0.0377 (7)	0.0332 (7)	0.0313 (6)	−0.0023 (6)	0.0080 (5)	−0.0038 (5)
C12	0.0345 (7)	0.0359 (7)	0.0299 (6)	0.0026 (5)	0.0059 (5)	−0.0019 (5)
C13	0.0388 (7)	0.0319 (7)	0.0354 (7)	−0.0014 (5)	0.0052 (6)	−0.0023 (5)
C14	0.0442 (8)	0.0379 (7)	0.0405 (7)	−0.0013 (6)	0.0081 (6)	−0.0002 (6)
C15	0.0536 (9)	0.0372 (8)	0.0383 (7)	0.0054 (6)	0.0014 (6)	−0.0027 (6)
C16	0.0757 (11)	0.0484 (9)	0.0467 (9)	0.0077 (8)	0.0025 (8)	0.0062 (7)
C17	0.1020 (16)	0.0568 (11)	0.0466 (10)	0.0234 (10)	−0.0011 (10)	0.0063 (8)
C18	0.0869 (14)	0.0723 (12)	0.0513 (10)	0.0402 (11)	−0.0081 (10)	−0.0061 (9)
C19	0.0580 (10)	0.0704 (11)	0.0524 (10)	0.0232 (9)	−0.0027 (8)	−0.0097 (9)
C20	0.0497 (9)	0.0462 (8)	0.0415 (8)	0.0089 (7)	−0.0003 (7)	−0.0087 (6)
C21	0.0388 (8)	0.0562 (9)	0.0499 (9)	0.0008 (7)	0.0079 (7)	−0.0064 (7)
C22	0.0397 (8)	0.0423 (8)	0.0442 (8)	−0.0018 (6)	0.0085 (6)	0.0011 (6)
C23	0.0343 (7)	0.0331 (7)	0.0309 (6)	0.0025 (5)	0.0050 (5)	0.0017 (5)
C24	0.0379 (7)	0.0387 (8)	0.0451 (8)	0.0051 (6)	0.0090 (6)	−0.0004 (6)
C25	0.0355 (8)	0.0557 (9)	0.0550 (9)	0.0011 (7)	0.0126 (7)	−0.0009 (7)
C26	0.0448 (8)	0.0470 (8)	0.0409 (8)	−0.0075 (6)	0.0096 (6)	0.0013 (6)
C27	0.0538 (10)	0.0681 (12)	0.0683 (11)	−0.0161 (9)	0.0188 (8)	0.0019 (9)
C28	0.0800 (13)	0.0545 (11)	0.0735 (12)	−0.0304 (10)	0.0180 (10)	0.0014 (9)
C29	0.0816 (13)	0.0412 (9)	0.0642 (11)	−0.0145 (8)	0.0184 (9)	0.0015 (8)
C30	0.0653 (10)	0.0363 (8)	0.0507 (9)	−0.0037 (7)	0.0133 (7)	0.0025 (7)
C31	0.0463 (8)	0.0384 (7)	0.0334 (7)	−0.0030 (6)	0.0067 (6)	0.0027 (6)
C32	0.0369 (7)	0.0365 (7)	0.0358 (7)	0.0027 (6)	0.0058 (6)	0.0023 (6)
C33	0.0406 (7)	0.0390 (7)	0.0402 (7)	−0.0054 (6)	0.0084 (6)	−0.0063 (6)
C34	0.0436 (8)	0.0497 (9)	0.0393 (8)	−0.0073 (6)	0.0067 (6)	−0.0009 (6)
C35	0.0422 (8)	0.0483 (8)	0.0336 (7)	0.0020 (6)	0.0046 (6)	0.0024 (6)
C36	0.0677 (11)	0.0549 (10)	0.0465 (9)	−0.0021 (8)	−0.0043 (8)	−0.0030 (7)

O1—C2	1.3602 (16)	C19—C20	1.422 (2)
O1—C33	1.4278 (16)	C19—H19	0.9500
O2—C7	1.3676 (16)	C20—C21	1.410 (2)
O2—C35	1.4351 (16)	C21—C22	1.365 (2)
O3—C11	1.2217 (15)	C21—H21	0.9500
O4—C12	1.2237 (15)	C22—H22	0.9500
C1—C2	1.3867 (18)	C23—C32	1.3653 (18)
C1—C9	1.4310 (18)	C23—C24	1.4164 (18)
C1—C11	1.5075 (17)	C24—C25	1.363 (2)
C2—C3	1.4117 (19)	C24—H24	0.9500
C3—C4	1.3583 (19)	C25—C26	1.415 (2)
C3—H3	0.9500	C25—H25	0.9500
C4—C10	1.4103 (19)	C26—C31	1.416 (2)
C4—H4	0.9500	C26—C27	1.422 (2)
C5—C6	1.3600 (19)	C27—C28	1.366 (3)
C5—C10	1.4086 (19)	C27—H27	0.9500
C5—H5	0.9500	C28—C29	1.394 (3)
C6—C7	1.4099 (19)	C28—H28	0.9500
C6—H6	0.9500	C29—C30	1.356 (2)
C7—C8	1.3852 (18)	C29—H29	0.9500
C8—C9	1.4332 (18)	C30—C31	1.418 (2)
C8—C12	1.5049 (18)	C30—H30	0.9500
C9—C10	1.4300 (18)	C31—C32	1.4112 (19)
C11—C13	1.4874 (18)	C32—H32	0.9500
C12—C23	1.4860 (18)	C33—C34	1.5004 (19)
C13—C14	1.3680 (19)	C33—H33A	0.9900
C13—C22	1.4145 (19)	C33—H33B	0.9900
C14—C15	1.414 (2)	C34—H34A	0.9800
C14—H14	0.9500	C34—H34B	0.9800
C15—C16	1.416 (2)	C34—H34C	0.9800
C15—C20	1.419 (2)	C35—C36	1.501 (2)
C16—C17	1.361 (2)	C35—H35A	0.9900
C16—H16	0.9500	C35—H35B	0.9900
C17—C18	1.406 (3)	C36—H36A	0.9800
C17—H17	0.9500	C36—H36B	0.9800
C18—C19	1.360 (3)	C36—H36C	0.9800
C18—H18	0.9500
C2—O1—C33	119.78 (10)	C15—C20—C19	118.60 (15)
C7—O2—C35	118.77 (10)	C22—C21—C20	120.90 (14)
C2—C1—C9	119.74 (12)	C22—C21—H21	119.6
C2—C1—C11	117.44 (11)	C20—C21—H21	119.6
C9—C1—C11	122.15 (11)	C21—C22—C13	120.41 (13)
O1—C2—C1	115.90 (11)	C21—C22—H22	119.8
O1—C2—C3	122.58 (12)	C13—C22—H22	119.8
C1—C2—C3	121.45 (12)	C32—C23—C24	119.41 (12)
C4—C3—C2	119.16 (13)	C32—C23—C12	119.19 (11)
C4—C3—H3	120.4	C24—C23—C12	121.39 (12)
C2—C3—H3	120.4	C25—C24—C23	120.57 (13)
C3—C4—C10	122.03 (13)	C25—C24—H24	119.7
C3—C4—H4	119.0	C23—C24—H24	119.7
C10—C4—H4	119.0	C24—C25—C26	120.79 (13)
C6—C5—C10	122.08 (13)	C24—C25—H25	119.6
C6—C5—H5	119.0	C26—C25—H25	119.6
C10—C5—H5	119.0	C25—C26—C31	118.94 (13)
C5—C6—C7	118.92 (13)	C25—C26—C27	122.96 (14)
C5—C6—H6	120.5	C31—C26—C27	118.09 (14)
C7—C6—H6	120.5	C28—C27—C26	120.42 (17)
O2—C7—C8	115.41 (11)	C28—C27—H27	119.8
O2—C7—C6	122.84 (12)	C26—C27—H27	119.8
C8—C7—C6	121.69 (12)	C27—C28—C29	121.30 (16)
C7—C8—C9	119.81 (12)	C27—C28—H28	119.4
C7—C8—C12	117.29 (11)	C29—C28—H28	119.4
C9—C8—C12	122.16 (11)	C30—C29—C28	119.88 (16)
C10—C9—C1	118.13 (12)	C30—C29—H29	120.1
C10—C9—C8	117.81 (12)	C28—C29—H29	120.1
C1—C9—C8	124.05 (12)	C29—C30—C31	121.01 (16)
C5—C10—C4	121.03 (12)	C29—C30—H30	119.5
C5—C10—C9	119.59 (12)	C31—C30—H30	119.5
C4—C10—C9	119.37 (12)	C32—C31—C26	118.77 (13)
O3—C11—C13	121.04 (11)	C32—C31—C30	121.95 (13)
O3—C11—C1	118.52 (11)	C26—C31—C30	119.28 (13)
C13—C11—C1	120.43 (11)	C23—C32—C31	121.50 (12)
O4—C12—C23	121.13 (12)	C23—C32—H32	119.3
O4—C12—C8	118.55 (11)	C31—C32—H32	119.3
C23—C12—C8	120.30 (11)	O1—C33—C34	106.08 (11)
C14—C13—C22	119.55 (13)	O1—C33—H33A	110.5
C14—C13—C11	119.60 (12)	C34—C33—H33A	110.5
C22—C13—C11	120.81 (12)	O1—C33—H33B	110.5
C13—C14—C15	121.49 (13)	C34—C33—H33B	110.5
C13—C14—H14	119.3	H33A—C33—H33B	108.7
C15—C14—H14	119.3	C33—C34—H34A	109.5
C14—C15—C16	122.46 (15)	C33—C34—H34B	109.5
C14—C15—C20	118.43 (13)	H34A—C34—H34B	109.5
C16—C15—C20	119.08 (14)	C33—C34—H34C	109.5
C17—C16—C15	120.76 (18)	H34A—C34—H34C	109.5
C17—C16—H16	119.6	H34B—C34—H34C	109.5
C15—C16—H16	119.6	O2—C35—C36	106.97 (12)
C16—C17—C18	120.22 (18)	O2—C35—H35A	110.3
C16—C17—H17	119.9	C36—C35—H35A	110.3
C18—C17—H17	119.9	O2—C35—H35B	110.3
C19—C18—C17	120.83 (17)	C36—C35—H35B	110.3
C19—C18—H18	119.6	H35A—C35—H35B	108.6
C17—C18—H18	119.6	C35—C36—H36A	109.5
C18—C19—C20	120.51 (18)	C35—C36—H36B	109.5
C18—C19—H19	119.7	H36A—C36—H36B	109.5
C20—C19—H19	119.7	C35—C36—H36C	109.5
C21—C20—C15	119.19 (13)	H36A—C36—H36C	109.5
C21—C20—C19	122.21 (15)	H36B—C36—H36C	109.5
C33—O1—C2—C1	−175.31 (11)	C22—C13—C14—C15	0.0 (2)
C33—O1—C2—C3	7.58 (19)	C11—C13—C14—C15	−177.80 (12)
C9—C1—C2—O1	−178.78 (11)	C13—C14—C15—C16	179.53 (14)
C11—C1—C2—O1	−7.94 (17)	C13—C14—C15—C20	1.5 (2)
C9—C1—C2—C3	−1.64 (19)	C14—C15—C16—C17	−177.36 (15)
C11—C1—C2—C3	169.20 (12)	C20—C15—C16—C17	0.7 (2)
O1—C2—C3—C4	175.83 (12)	C15—C16—C17—C18	−0.5 (3)
C1—C2—C3—C4	−1.1 (2)	C16—C17—C18—C19	0.1 (3)
C2—C3—C4—C10	1.7 (2)	C17—C18—C19—C20	0.1 (3)
C10—C5—C6—C7	1.1 (2)	C14—C15—C20—C21	−1.5 (2)
C35—O2—C7—C8	−177.25 (11)	C16—C15—C20—C21	−179.60 (14)
C35—O2—C7—C6	5.50 (18)	C14—C15—C20—C19	177.69 (13)
C5—C6—C7—O2	174.74 (12)	C16—C15—C20—C19	−0.4 (2)
C5—C6—C7—C8	−2.3 (2)	C18—C19—C20—C21	179.21 (16)
O2—C7—C8—C9	−176.70 (11)	C18—C19—C20—C15	0.0 (2)
C6—C7—C8—C9	0.58 (19)	C15—C20—C21—C22	0.0 (2)
O2—C7—C8—C12	−6.34 (16)	C19—C20—C21—C22	−179.14 (14)
C6—C7—C8—C12	170.94 (12)	C20—C21—C22—C13	1.5 (2)
C2—C1—C9—C10	3.69 (17)	C14—C13—C22—C21	−1.5 (2)
C11—C1—C9—C10	−166.70 (11)	C11—C13—C22—C21	176.23 (12)
C2—C1—C9—C8	−175.25 (12)	O4—C12—C23—C32	14.09 (18)
C11—C1—C9—C8	14.35 (18)	C8—C12—C23—C32	−164.40 (12)
C7—C8—C9—C10	2.31 (17)	O4—C12—C23—C24	−165.25 (12)
C12—C8—C9—C10	−167.56 (11)	C8—C12—C23—C24	16.25 (18)
C7—C8—C9—C1	−178.74 (11)	C32—C23—C24—C25	−0.6 (2)
C12—C8—C9—C1	11.38 (19)	C12—C23—C24—C25	178.77 (13)
C6—C5—C10—C4	−177.56 (13)	C23—C24—C25—C26	0.8 (2)
C6—C5—C10—C9	1.8 (2)	C24—C25—C26—C31	0.2 (2)
C3—C4—C10—C5	179.80 (12)	C24—C25—C26—C27	179.46 (15)
C3—C4—C10—C9	0.4 (2)	C25—C26—C27—C28	−177.82 (16)
C1—C9—C10—C5	177.50 (11)	C31—C26—C27—C28	1.4 (2)
C8—C9—C10—C5	−3.49 (18)	C26—C27—C28—C29	−0.2 (3)
C1—C9—C10—C4	−3.10 (18)	C27—C28—C29—C30	−1.1 (3)
C8—C9—C10—C4	175.91 (11)	C28—C29—C30—C31	1.1 (3)
C2—C1—C11—O3	−117.99 (13)	C25—C26—C31—C32	−1.4 (2)
C9—C1—C11—O3	52.62 (17)	C27—C26—C31—C32	179.34 (14)
C2—C1—C11—C13	60.82 (16)	C25—C26—C31—C30	177.88 (14)
C9—C1—C11—C13	−128.58 (13)	C27—C26—C31—C30	−1.4 (2)
C7—C8—C12—O4	−111.96 (14)	C29—C30—C31—C32	179.38 (14)
C9—C8—C12—O4	58.15 (17)	C29—C30—C31—C26	0.1 (2)
C7—C8—C12—C23	66.57 (15)	C24—C23—C32—C31	−0.64 (19)
C9—C8—C12—C23	−123.31 (13)	C12—C23—C32—C31	180.00 (12)
O3—C11—C13—C14	21.18 (19)	C26—C31—C32—C23	1.62 (19)
C1—C11—C13—C14	−157.60 (12)	C30—C31—C32—C23	−177.63 (13)
O3—C11—C13—C22	−156.59 (13)	C2—O1—C33—C34	171.47 (11)
C1—C11—C13—C22	24.64 (18)	C7—O2—C35—C36	176.89 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C21—H21···O3i	0.95	2.45	3.3958 (18)	173
C25—H25···O4ii	0.95	2.45	3.3996 (18)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21⋯O3i	0.95	2.45	3.3958 (18)	173
C25—H25⋯O4ii	0.95	2.45	3.3996 (18)	176

Symmetry codes: (i) ; (ii) .