(8-Benzoyl-2,7-dimeth-oxy-naphthalen-1-yl)(4-phen-oxy-phen-yl)methanone.

In the mol-ecule of the title compound, C32H24O5, the benzoyl group and the 4-phenoxy substituted benzoyl group at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel. The two benzene rings make a dihedral angle of 21.18 (10)°, and are inclined to the naphthalene ring system by 86.53 (9) and 82.95 (8)°, respectively. In the crystal, C-H⋯O inter-actions are observed involving aromatic and meth-oxy H atoms with ketonic carbonyl O atoms, as well as C-H⋯π inter-actions between aromatic H atoms and the π-systems of naphthalene and benzene rings. These interactions form a three-dimensional architecture and afford a waved alignment of the naphthalene ring systems along the c axis.

Related literature

For the synthesis 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: Nakaema et al. (2008 ▶); Hijikata et al. (2010 ▶); Sasagawa et al. (2011 ▶, 2013 ▶); Muto et al. (2012 ▶).

Experimental

Crystal data

C32H24O5

M = 488.51

Orthorhombic,

a = 8.19645 (10) Å

b = 11.5051 (2) Å

c = 26.4916 (4) Å

V = 2498.18 (7) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 193 K

0.60 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Rigaku, 1995 ▶) T min = 0.802, T max = 0.868

46867 measured reflections

2605 independent reflections

2543 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.085

S = 1.04

2605 reflections

337 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.14 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/S1600536813004303/vm2188sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004303/vm2188Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813004303/vm2188Isup3.cml

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

C32H24O5	F(000) = 1024
Mr = 488.51	Dx = 1.299 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: P 2ac 2ab	Cell parameters from 44479 reflections
a = 8.19645 (10) Å	θ = 3.3–68.3°
b = 11.5051 (2) Å	µ = 0.71 mm−1
c = 26.4916 (4) Å	T = 193 K
V = 2498.18 (7) Å3	Block, colourless
Z = 4	0.60 × 0.30 × 0.20 mm

Rigaku R-AXIS RAPID diffractometer	2605 independent reflections
Radiation source: rotating anode	2543 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 10.000 pixels mm-1	θmax = 68.3°, θmin = 3.3°
ω scans	h = −9→9
Absorption correction: multi-scan (ABSCOR; Rigaku, 1995)	k = −13→13
Tmin = 0.802, Tmax = 0.868	l = −31→31
46867 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)] = 0.032	H-atom parameters constrained
wR(F2) = 0.085	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.3758P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2605 reflections	Δρmax = 0.19 e Å−3
337 parameters	Δρmin = −0.14 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: 0.0019 (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	0.31166 (15)	0.05570 (11)	0.41889 (5)	0.0395 (3)
O2	−0.2584 (2)	−0.31098 (13)	0.44425 (6)	0.0630 (5)
O3	0.08516 (19)	0.16347 (12)	0.50987 (4)	0.0461 (3)
O4	0.1135 (2)	0.25452 (15)	0.24234 (5)	0.0582 (4)
O5	0.11094 (17)	0.02780 (12)	0.31322 (5)	0.0429 (3)
C1	0.0961 (2)	0.19406 (14)	0.42338 (6)	0.0334 (4)
C2	0.0552 (2)	0.23680 (15)	0.47042 (7)	0.0374 (4)
C3	−0.0139 (3)	0.34833 (17)	0.47642 (7)	0.0429 (4)
H3	−0.0370	0.3778	0.5091	0.051*
C4	−0.0469 (2)	0.41295 (15)	0.43472 (7)	0.0432 (4)
H4	−0.0976	0.4867	0.4387	0.052*
C5	−0.0081 (2)	0.37364 (15)	0.38559 (7)	0.0381 (4)
C6	−0.0466 (3)	0.44090 (16)	0.34258 (8)	0.0450 (4)
H6	−0.0998	0.5136	0.3469	0.054*
C7	−0.0093 (3)	0.40417 (18)	0.29486 (8)	0.0475 (5)
H7	−0.0373	0.4501	0.2663	0.057*
C8	0.0710 (2)	0.29759 (18)	0.28879 (7)	0.0416 (4)
C9	0.1126 (2)	0.22877 (15)	0.32944 (6)	0.0347 (4)
C10	0.0701 (2)	0.26357 (14)	0.37942 (6)	0.0328 (4)
C11	0.1648 (2)	0.07161 (15)	0.42218 (6)	0.0330 (4)
C12	0.0487 (2)	−0.02714 (15)	0.42656 (6)	0.0353 (4)
C13	0.1101 (3)	−0.13927 (16)	0.43272 (7)	0.0421 (4)
H13	0.2247	−0.1516	0.4335	0.050*
C14	0.0055 (3)	−0.23210 (16)	0.43770 (8)	0.0476 (5)
H14	0.0477	−0.3083	0.4422	0.057*
C15	−0.1609 (3)	−0.21421 (18)	0.43615 (7)	0.0466 (5)
C16	−0.2252 (3)	−0.10405 (19)	0.42947 (8)	0.0512 (5)
H16	−0.3399	−0.0925	0.4280	0.061*
C17	−0.1191 (3)	−0.01104 (17)	0.42499 (8)	0.0436 (4)
H17	−0.1618	0.0651	0.4208	0.052*
C18	−0.3900 (3)	−0.33373 (16)	0.41261 (7)	0.0440 (4)
C19	−0.3950 (3)	−0.3008 (2)	0.36259 (8)	0.0556 (5)
H19	−0.3112	−0.2534	0.3488	0.067*
C20	−0.5230 (3)	−0.3373 (2)	0.33277 (9)	0.0665 (7)
H20	−0.5275	−0.3144	0.2983	0.080*
C21	−0.6440 (3)	−0.4065 (2)	0.35234 (11)	0.0697 (7)
H21	−0.7308	−0.4327	0.3315	0.084*
C22	−0.6383 (3)	−0.4377 (2)	0.40272 (10)	0.0657 (7)
H22	−0.7229	−0.4843	0.4166	0.079*
C23	−0.5117 (3)	−0.40221 (19)	0.43289 (8)	0.0536 (5)
H23	−0.5079	−0.4245	0.4674	0.064*
C24	0.0591 (3)	0.2062 (2)	0.55989 (7)	0.0537 (5)
H24A	−0.0567	0.2248	0.5644	0.064*
H24B	0.1247	0.2763	0.5652	0.064*
H24C	0.0914	0.1466	0.5844	0.064*
C25	0.0032 (3)	0.2714 (2)	0.20238 (8)	0.0599 (6)
H25A	0.0191	0.2106	0.1770	0.072*
H25B	0.0223	0.3477	0.1870	0.072*
H25C	−0.1087	0.2677	0.2153	0.072*
C26	0.1933 (2)	0.11466 (16)	0.31671 (6)	0.0340 (4)
C27	0.3730 (2)	0.11156 (18)	0.30852 (6)	0.0375 (4)
C28	0.4689 (2)	0.2093 (2)	0.31499 (7)	0.0458 (5)
H28	0.4203	0.2820	0.3230	0.055*
C29	0.6378 (3)	0.2002 (3)	0.30959 (9)	0.0597 (6)
H29	0.7048	0.2666	0.3146	0.072*
C30	0.7076 (3)	0.0954 (3)	0.29705 (9)	0.0633 (6)
H30	0.8226	0.0898	0.2935	0.076*
C31	0.6119 (3)	−0.0014 (2)	0.28961 (10)	0.0641 (6)
H31	0.6606	−0.0733	0.2804	0.077*
C32	0.4452 (3)	0.0062 (2)	0.29560 (9)	0.0519 (5)
H32	0.3793	−0.0609	0.2909	0.062*

	U11	U22	U33	U12	U13	U23
O1	0.0357 (7)	0.0423 (7)	0.0407 (6)	0.0005 (6)	−0.0008 (5)	−0.0043 (5)
O2	0.0731 (11)	0.0508 (8)	0.0652 (9)	−0.0268 (8)	−0.0251 (9)	0.0206 (7)
O3	0.0606 (9)	0.0469 (7)	0.0309 (6)	0.0056 (7)	0.0013 (6)	−0.0039 (5)
O4	0.0563 (9)	0.0850 (11)	0.0335 (6)	0.0205 (9)	0.0023 (6)	0.0061 (7)
O5	0.0376 (7)	0.0425 (7)	0.0486 (7)	−0.0058 (6)	0.0001 (6)	−0.0108 (6)
C1	0.0326 (9)	0.0323 (8)	0.0353 (8)	−0.0049 (7)	0.0005 (7)	−0.0028 (7)
C2	0.0385 (9)	0.0365 (9)	0.0373 (8)	−0.0046 (8)	0.0015 (8)	−0.0042 (7)
C3	0.0465 (11)	0.0398 (9)	0.0423 (10)	−0.0036 (9)	0.0075 (9)	−0.0118 (8)
C4	0.0442 (10)	0.0293 (8)	0.0562 (11)	−0.0002 (8)	0.0080 (9)	−0.0082 (8)
C5	0.0358 (9)	0.0293 (8)	0.0492 (10)	−0.0041 (8)	0.0034 (8)	−0.0003 (7)
C6	0.0432 (10)	0.0326 (9)	0.0594 (11)	0.0010 (8)	0.0046 (9)	0.0058 (8)
C7	0.0460 (11)	0.0468 (10)	0.0497 (10)	0.0018 (10)	0.0007 (9)	0.0144 (9)
C8	0.0363 (10)	0.0498 (10)	0.0386 (9)	−0.0014 (9)	0.0035 (8)	0.0065 (8)
C9	0.0296 (8)	0.0373 (9)	0.0372 (9)	−0.0028 (8)	0.0005 (7)	0.0010 (7)
C10	0.0305 (8)	0.0301 (8)	0.0377 (8)	−0.0050 (7)	0.0012 (7)	−0.0025 (7)
C11	0.0395 (9)	0.0338 (8)	0.0257 (7)	−0.0016 (7)	−0.0016 (7)	−0.0032 (6)
C12	0.0418 (10)	0.0333 (8)	0.0308 (8)	−0.0028 (8)	−0.0026 (7)	−0.0009 (7)
C13	0.0450 (10)	0.0371 (9)	0.0441 (10)	0.0008 (9)	−0.0056 (9)	−0.0009 (8)
C14	0.0607 (13)	0.0321 (9)	0.0501 (10)	−0.0026 (9)	−0.0120 (10)	0.0028 (8)
C15	0.0568 (12)	0.0402 (10)	0.0429 (9)	−0.0141 (9)	−0.0099 (9)	0.0061 (8)
C16	0.0432 (11)	0.0484 (11)	0.0619 (12)	−0.0089 (10)	−0.0056 (10)	0.0059 (10)
C17	0.0440 (10)	0.0346 (9)	0.0523 (11)	−0.0014 (8)	−0.0006 (9)	0.0021 (8)
C18	0.0490 (11)	0.0372 (9)	0.0457 (10)	−0.0064 (9)	−0.0048 (9)	0.0007 (8)
C19	0.0554 (13)	0.0614 (13)	0.0500 (11)	−0.0127 (12)	−0.0002 (10)	0.0091 (10)
C20	0.0739 (17)	0.0763 (15)	0.0492 (12)	−0.0144 (15)	−0.0147 (12)	0.0059 (11)
C21	0.0610 (15)	0.0718 (15)	0.0764 (15)	−0.0165 (14)	−0.0230 (13)	0.0024 (13)
C22	0.0521 (13)	0.0650 (15)	0.0799 (16)	−0.0196 (13)	−0.0008 (12)	0.0079 (12)
C23	0.0609 (13)	0.0502 (11)	0.0498 (11)	−0.0139 (11)	0.0020 (10)	0.0055 (9)
C24	0.0649 (14)	0.0632 (12)	0.0329 (9)	0.0060 (12)	0.0038 (9)	−0.0084 (9)
C25	0.0696 (15)	0.0599 (13)	0.0503 (11)	0.0168 (13)	−0.0132 (11)	−0.0093 (10)
C26	0.0340 (9)	0.0408 (9)	0.0273 (7)	−0.0001 (8)	−0.0015 (7)	−0.0035 (7)
C27	0.0330 (9)	0.0494 (10)	0.0301 (8)	0.0016 (8)	−0.0010 (7)	0.0007 (8)
C28	0.0383 (10)	0.0595 (12)	0.0395 (9)	−0.0057 (10)	0.0019 (8)	−0.0073 (9)
C29	0.0379 (11)	0.0877 (17)	0.0536 (12)	−0.0151 (12)	0.0018 (9)	−0.0076 (12)
C30	0.0320 (10)	0.0962 (19)	0.0618 (13)	0.0077 (13)	0.0013 (10)	0.0102 (14)
C31	0.0475 (12)	0.0696 (15)	0.0753 (15)	0.0188 (12)	0.0093 (12)	0.0099 (13)
C32	0.0427 (11)	0.0504 (12)	0.0625 (13)	0.0074 (10)	0.0058 (10)	0.0041 (10)

O1—C11	1.220 (2)	C16—C17	1.384 (3)
O2—C15	1.387 (2)	C16—H16	0.9500
O2—C18	1.391 (2)	C17—H17	0.9500
O3—C2	1.365 (2)	C18—C19	1.379 (3)
O3—C24	1.429 (2)	C18—C23	1.380 (3)
O4—C8	1.372 (2)	C19—C20	1.378 (3)
O4—C25	1.406 (3)	C19—H19	0.9500
O5—C26	1.209 (2)	C20—C21	1.374 (4)
C1—C2	1.381 (2)	C20—H20	0.9500
C1—C10	1.429 (2)	C21—C22	1.383 (4)
C1—C11	1.518 (2)	C21—H21	0.9500
C2—C3	1.412 (3)	C22—C23	1.372 (3)
C3—C4	1.359 (3)	C22—H22	0.9500
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.414 (3)	C24—H24A	0.9800
C4—H4	0.9500	C24—H24B	0.9800
C5—C6	1.413 (3)	C24—H24C	0.9800
C5—C10	1.428 (2)	C25—H25A	0.9800
C6—C7	1.368 (3)	C25—H25B	0.9800
C6—H6	0.9500	C25—H25C	0.9800
C7—C8	1.401 (3)	C26—C27	1.489 (2)
C7—H7	0.9500	C27—C28	1.383 (3)
C8—C9	1.379 (3)	C27—C32	1.392 (3)
C9—C10	1.427 (2)	C28—C29	1.396 (3)
C9—C26	1.508 (3)	C28—H28	0.9500
C11—C12	1.487 (2)	C29—C30	1.375 (4)
C12—C17	1.388 (3)	C29—H29	0.9500
C12—C13	1.394 (3)	C30—C31	1.377 (4)
C13—C14	1.376 (3)	C30—H30	0.9500
C13—H13	0.9500	C31—C32	1.378 (3)
C14—C15	1.380 (3)	C31—H31	0.9500
C14—H14	0.9500	C32—H32	0.9500
C15—C16	1.384 (3)
C15—O2—C18	120.31 (15)	C12—C17—H17	119.4
C2—O3—C24	118.06 (16)	C19—C18—C23	120.6 (2)
C8—O4—C25	117.51 (17)	C19—C18—O2	123.43 (19)
C2—C1—C10	120.00 (15)	C23—C18—O2	115.69 (18)
C2—C1—C11	116.07 (15)	C20—C19—C18	119.3 (2)
C10—C1—C11	123.92 (15)	C20—C19—H19	120.3
O3—C2—C1	115.28 (15)	C18—C19—H19	120.3
O3—C2—C3	123.22 (16)	C21—C20—C19	120.7 (2)
C1—C2—C3	121.50 (16)	C21—C20—H20	119.7
C4—C3—C2	119.07 (17)	C19—C20—H20	119.7
C4—C3—H3	120.5	C20—C21—C22	119.4 (2)
C2—C3—H3	120.5	C20—C21—H21	120.3
C3—C4—C5	121.89 (17)	C22—C21—H21	120.3
C3—C4—H4	119.1	C23—C22—C21	120.7 (2)
C5—C4—H4	119.1	C23—C22—H22	119.6
C6—C5—C4	121.11 (17)	C21—C22—H22	119.6
C6—C5—C10	119.57 (16)	C22—C23—C18	119.3 (2)
C4—C5—C10	119.32 (16)	C22—C23—H23	120.3
C7—C6—C5	121.75 (17)	C18—C23—H23	120.3
C7—C6—H6	119.1	O3—C24—H24A	109.5
C5—C6—H6	119.1	O3—C24—H24B	109.5
C6—C7—C8	118.78 (17)	H24A—C24—H24B	109.5
C6—C7—H7	120.6	O3—C24—H24C	109.5
C8—C7—H7	120.6	H24A—C24—H24C	109.5
O4—C8—C9	115.46 (17)	H24B—C24—H24C	109.5
O4—C8—C7	122.59 (17)	O4—C25—H25A	109.5
C9—C8—C7	121.95 (17)	O4—C25—H25B	109.5
C8—C9—C10	120.18 (17)	H25A—C25—H25B	109.5
C8—C9—C26	115.71 (16)	O4—C25—H25C	109.5
C10—C9—C26	123.98 (15)	H25A—C25—H25C	109.5
C9—C10—C5	117.68 (15)	H25B—C25—H25C	109.5
C9—C10—C1	124.26 (15)	O5—C26—C27	121.40 (18)
C5—C10—C1	118.03 (15)	O5—C26—C9	119.47 (15)
O1—C11—C12	121.49 (16)	C27—C26—C9	119.13 (17)
O1—C11—C1	120.45 (16)	C28—C27—C32	119.81 (18)
C12—C11—C1	118.04 (15)	C28—C27—C26	121.65 (19)
C17—C12—C13	118.98 (18)	C32—C27—C26	118.52 (19)
C17—C12—C11	122.00 (17)	C27—C28—C29	119.3 (2)
C13—C12—C11	119.02 (17)	C27—C28—H28	120.3
C14—C13—C12	120.31 (19)	C29—C28—H28	120.3
C14—C13—H13	119.8	C30—C29—C28	120.2 (2)
C12—C13—H13	119.8	C30—C29—H29	119.9
C13—C14—C15	119.80 (19)	C28—C29—H29	119.9
C13—C14—H14	120.1	C29—C30—C31	120.5 (2)
C15—C14—H14	120.1	C29—C30—H30	119.8
C14—C15—C16	121.14 (19)	C31—C30—H30	119.8
C14—C15—O2	116.44 (19)	C30—C31—C32	119.8 (2)
C16—C15—O2	122.33 (19)	C30—C31—H31	120.1
C17—C16—C15	118.6 (2)	C32—C31—H31	120.1
C17—C16—H16	120.7	C31—C32—C27	120.3 (2)
C15—C16—H16	120.7	C31—C32—H32	119.8
C16—C17—C12	121.12 (19)	C27—C32—H32	119.8
C16—C17—H17	119.4
C24—O3—C2—C1	174.60 (18)	O1—C11—C12—C13	7.3 (3)
C24—O3—C2—C3	−5.9 (3)	C1—C11—C12—C13	−171.04 (16)
C10—C1—C2—O3	−179.94 (15)	C17—C12—C13—C14	−0.7 (3)
C11—C1—C2—O3	1.2 (2)	C11—C12—C13—C14	178.93 (16)
C10—C1—C2—C3	0.6 (3)	C12—C13—C14—C15	0.6 (3)
C11—C1—C2—C3	−178.30 (16)	C13—C14—C15—C16	0.2 (3)
O3—C2—C3—C4	−176.71 (18)	C13—C14—C15—O2	−176.52 (16)
C1—C2—C3—C4	2.7 (3)	C18—O2—C15—C14	−133.4 (2)
C2—C3—C4—C5	−2.6 (3)	C18—O2—C15—C16	49.9 (3)
C3—C4—C5—C6	178.59 (19)	C14—C15—C16—C17	−0.8 (3)
C3—C4—C5—C10	−0.8 (3)	O2—C15—C16—C17	175.70 (19)
C4—C5—C6—C7	179.8 (2)	C15—C16—C17—C12	0.7 (3)
C10—C5—C6—C7	−0.8 (3)	C13—C12—C17—C16	0.1 (3)
C5—C6—C7—C8	−0.8 (3)	C11—C12—C17—C16	−179.56 (17)
C25—O4—C8—C9	141.6 (2)	C15—O2—C18—C19	29.0 (3)
C25—O4—C8—C7	−38.4 (3)	C15—O2—C18—C23	−157.0 (2)
C6—C7—C8—O4	−179.69 (19)	C23—C18—C19—C20	−0.3 (4)
C6—C7—C8—C9	0.3 (3)	O2—C18—C19—C20	173.4 (2)
O4—C8—C9—C10	−178.22 (17)	C18—C19—C20—C21	−0.5 (4)
C7—C8—C9—C10	1.8 (3)	C19—C20—C21—C22	1.2 (4)
O4—C8—C9—C26	−2.1 (2)	C20—C21—C22—C23	−1.3 (4)
C7—C8—C9—C26	177.96 (17)	C21—C22—C23—C18	0.6 (4)
C8—C9—C10—C5	−3.3 (3)	C19—C18—C23—C22	0.2 (4)
C26—C9—C10—C5	−179.09 (16)	O2—C18—C23—C22	−174.0 (2)
C8—C9—C10—C1	174.74 (17)	C8—C9—C26—O5	−94.6 (2)
C26—C9—C10—C1	−1.0 (3)	C10—C9—C26—O5	81.4 (2)
C6—C5—C10—C9	2.8 (3)	C8—C9—C26—C27	85.2 (2)
C4—C5—C10—C9	−177.78 (17)	C10—C9—C26—C27	−98.9 (2)
C6—C5—C10—C1	−175.38 (17)	O5—C26—C27—C28	−176.63 (17)
C4—C5—C10—C1	4.1 (2)	C9—C26—C27—C28	3.6 (3)
C2—C1—C10—C9	178.04 (17)	O5—C26—C27—C32	1.3 (3)
C11—C1—C10—C9	−3.2 (3)	C9—C26—C27—C32	−178.47 (17)
C2—C1—C10—C5	−3.9 (2)	C32—C27—C28—C29	−1.5 (3)
C11—C1—C10—C5	174.87 (15)	C26—C27—C28—C29	176.44 (18)
C2—C1—C11—O1	−100.0 (2)	C27—C28—C29—C30	1.2 (3)
C10—C1—C11—O1	81.2 (2)	C28—C29—C30—C31	0.1 (4)
C2—C1—C11—C12	78.3 (2)	C29—C30—C31—C32	−1.1 (4)
C10—C1—C11—C12	−100.50 (19)	C30—C31—C32—C27	0.8 (4)
O1—C11—C12—C17	−173.09 (18)	C28—C27—C32—C31	0.5 (3)
C1—C11—C12—C17	8.6 (2)	C26—C27—C32—C31	−177.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C30—H30···O5i	0.95	2.52	3.423 (3)	158
C7—H7···O5ii	0.95	2.37	3.304 (3)	168
C25—H25B···O5ii	0.98	2.34	3.122 (3)	136
C3—H3···O1iii	0.95	2.40	3.310 (2)	160
C20—H20···Cg1iv	0.95	2.84	3.652 (3)	144
C23—H23···Cg2v	0.95	2.76	3.628 (2)	151
C29—H29···Cg3i	0.95	2.85	3.652 (3)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the C27–C32, C12–C17 and C5–C10 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C30—H30⋯O5i	0.95	2.52	3.423 (3)	158
C7—H7⋯O5ii	0.95	2.37	3.304 (3)	168
C25—H25B⋯O5ii	0.98	2.34	3.122 (3)	136
C3—H3⋯O1iii	0.95	2.40	3.310 (2)	160
C20—H20⋯Cg1iv	0.95	2.84	3.652 (3)	144
C23—H23⋯Cg2v	0.95	2.76	3.628 (2)	151
C29—H29⋯Cg3i	0.95	2.85	3.652 (3)	142

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