1,8-Dibenzoyl-naph-tha-lene-2,7-diyl dibenzoate.

In the title compound, C(38)H(24)O(6), the phenyl rings of the benzoyl and benzo-yloxy groups make dihedral angles of 67.12 (5), 85.15 (5), 76.41 (5) and 71.47 (5)° with the naphthal-ene ring system. In the crystal, C-H⋯O hydrogen bonds link mol-ecules into chains parallel to the b axis. The structure also features C-H⋯π and π-π stacking inter-actions, with centroid-centroid distances in the range 3.6441 (7)-3.9197 (8) Å.

Related literature

For electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶). For the structures of closely related compounds, see: Mitsui et al. (2008 ▶); Nakaema, Imaizumi et al. (2008 ▶); Nakaema, Watanabe et al. (2008 ▶); Mitsui et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C38H24O6

M = 576.57

Orthorhombic,

a = 18.0080 (3) Å

b = 12.4307 (2) Å

c = 25.3332 (4) Å

V = 5670.89 (16) Å3

Z = 8

Cu Kα radiation

μ = 0.74 mm−1

T = 193 K

0.40 × 0.40 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.756, T max = 0.930

95847 measured reflections

5182 independent reflections

4687 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.084

S = 1.05

5182 reflections

398 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.16 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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812030991/rz2784sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812030991/rz2784Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812030991/rz2784Isup3.cml

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

C38H24O6	F(000) = 2400
Mr = 576.57	Dx = 1.351 Mg m−3
Orthorhombic, Pbca	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 84271 reflections
a = 18.0080 (3) Å	θ = 3.0–68.2°
b = 12.4307 (2) Å	µ = 0.74 mm−1
c = 25.3332 (4) Å	T = 193 K
V = 5670.89 (16) Å3	Block, colourless
Z = 8	0.40 × 0.40 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	5182 independent reflections
Radiation source: rotating anode	4687 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.5°
ω scans	h = −21→21
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −14→14
Tmin = 0.756, Tmax = 0.930	l = −30→29
95847 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) = 0.084	w = 1/[σ2(Fo2) + (0.0397P)2 + 1.6474P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
5182 reflections	Δρmax = 0.18 e Å−3
398 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: 0.00092 (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	0.61898 (5)	0.15763 (7)	0.34605 (3)	0.0370 (2)
O2	0.50065 (5)	−0.02769 (7)	0.35288 (4)	0.0409 (2)
O3	0.75228 (4)	0.08534 (7)	0.45140 (3)	0.0338 (2)
O4	0.76608 (5)	−0.06529 (8)	0.50018 (4)	0.0467 (2)
O5	0.35421 (4)	0.12464 (6)	0.40337 (3)	0.03133 (19)
O6	0.32765 (5)	0.30188 (7)	0.40896 (4)	0.0435 (2)
C1	0.62268 (6)	0.09205 (9)	0.43251 (5)	0.0292 (2)
C2	0.67885 (6)	0.09509 (9)	0.46926 (5)	0.0318 (3)
C3	0.66720 (7)	0.11854 (10)	0.52281 (5)	0.0350 (3)
H3	0.7077	0.1205	0.5468	0.042*
C4	0.59685 (7)	0.13832 (10)	0.53959 (5)	0.0343 (3)
H4	0.5883	0.1540	0.5758	0.041*
C5	0.53608 (6)	0.13602 (9)	0.50417 (5)	0.0300 (2)
C6	0.46371 (6)	0.15936 (9)	0.52283 (5)	0.0323 (3)
H6	0.4564	0.1737	0.5593	0.039*
C7	0.40452 (6)	0.16164 (9)	0.48963 (5)	0.0323 (3)
H7	0.3564	0.1797	0.5022	0.039*
C8	0.41618 (6)	0.13662 (9)	0.43633 (5)	0.0292 (2)
C9	0.48431 (6)	0.11040 (9)	0.41559 (4)	0.0280 (2)
C10	0.54791 (6)	0.11234 (9)	0.44988 (5)	0.0279 (2)
C11	0.64142 (6)	0.08607 (9)	0.37478 (5)	0.0300 (3)
C12	0.68743 (6)	−0.00277 (9)	0.35355 (5)	0.0315 (3)
C13	0.69647 (7)	−0.09995 (10)	0.38020 (5)	0.0346 (3)
H13	0.6726	−0.1109	0.4132	0.042*
C14	0.73998 (7)	−0.18031 (11)	0.35889 (5)	0.0411 (3)
H14	0.7463	−0.2462	0.3774	0.049*
C15	0.77445 (8)	−0.16499 (11)	0.31054 (6)	0.0449 (3)
H15	0.8046	−0.2201	0.2959	0.054*
C16	0.76479 (8)	−0.06924 (12)	0.28359 (6)	0.0459 (3)
H16	0.7880	−0.0591	0.2503	0.055*
C17	0.72179 (7)	0.01137 (11)	0.30470 (5)	0.0395 (3)
H17	0.7155	0.0769	0.2860	0.047*
C18	0.48452 (6)	0.06636 (9)	0.35992 (5)	0.0306 (3)
C19	0.46058 (6)	0.13750 (10)	0.31580 (5)	0.0337 (3)
C20	0.42928 (7)	0.09152 (13)	0.27092 (5)	0.0463 (3)
H20	0.4224	0.0158	0.2690	0.056*
C21	0.40808 (9)	0.15631 (17)	0.22901 (6)	0.0618 (5)
H21	0.3850	0.1252	0.1990	0.074*
C22	0.42038 (8)	0.26547 (17)	0.23072 (6)	0.0623 (5)
H22	0.4071	0.3092	0.2014	0.075*
C23	0.45204 (8)	0.31167 (13)	0.27503 (6)	0.0531 (4)
H23	0.4608	0.3870	0.2761	0.064*
C24	0.47094 (7)	0.24812 (11)	0.31782 (5)	0.0408 (3)
H24	0.4911	0.2803	0.3487	0.049*
C25	0.79254 (7)	0.00012 (10)	0.47096 (5)	0.0346 (3)
C26	0.86968 (6)	−0.00040 (10)	0.45085 (5)	0.0331 (3)
C27	0.91357 (7)	−0.08882 (11)	0.46329 (6)	0.0406 (3)
H27	0.8934	−0.1465	0.4833	0.049*
C28	0.98659 (8)	−0.09286 (11)	0.44665 (6)	0.0438 (3)
H28	1.0165	−0.1534	0.4552	0.053*
C29	1.01600 (7)	−0.00930 (12)	0.41776 (6)	0.0454 (3)
H29	1.0663	−0.0121	0.4065	0.054*
C30	0.97251 (8)	0.07880 (12)	0.40502 (6)	0.0476 (3)
H30	0.9930	0.1362	0.3850	0.057*
C31	0.89918 (7)	0.08345 (11)	0.42147 (5)	0.0407 (3)
H31	0.8693	0.1438	0.4127	0.049*
C32	0.31154 (6)	0.21336 (10)	0.39400 (5)	0.0321 (3)
C33	0.24452 (6)	0.18511 (10)	0.36282 (5)	0.0327 (3)
C34	0.22400 (7)	0.07882 (11)	0.35420 (6)	0.0433 (3)
H34	0.2530	0.0220	0.3684	0.052*
C35	0.16118 (8)	0.05601 (13)	0.32482 (6)	0.0516 (4)
H35	0.1475	−0.0167	0.3186	0.062*
C36	0.11833 (7)	0.13831 (14)	0.30455 (6)	0.0500 (4)
H36	0.0756	0.1222	0.2840	0.060*
C37	0.13754 (7)	0.24401 (14)	0.31411 (6)	0.0495 (4)
H37	0.1074	0.3006	0.3009	0.059*
C38	0.20081 (7)	0.26746 (12)	0.34296 (5)	0.0419 (3)
H38	0.2143	0.3403	0.3492	0.050*

	U11	U22	U33	U12	U13	U23
O1	0.0313 (4)	0.0409 (5)	0.0387 (5)	0.0039 (4)	0.0022 (4)	0.0094 (4)
O2	0.0448 (5)	0.0337 (5)	0.0442 (5)	0.0012 (4)	0.0010 (4)	−0.0063 (4)
O3	0.0234 (4)	0.0391 (5)	0.0387 (5)	0.0006 (3)	−0.0019 (3)	0.0049 (4)
O4	0.0345 (5)	0.0486 (5)	0.0571 (6)	−0.0002 (4)	0.0024 (4)	0.0164 (5)
O5	0.0238 (4)	0.0337 (4)	0.0366 (5)	0.0009 (3)	−0.0027 (3)	−0.0019 (3)
O6	0.0383 (5)	0.0340 (5)	0.0582 (6)	−0.0002 (4)	−0.0092 (4)	−0.0045 (4)
C1	0.0269 (6)	0.0265 (5)	0.0341 (6)	−0.0005 (4)	0.0007 (5)	0.0016 (5)
C2	0.0251 (6)	0.0323 (6)	0.0379 (7)	−0.0010 (4)	0.0001 (5)	0.0024 (5)
C3	0.0307 (6)	0.0393 (7)	0.0351 (7)	−0.0027 (5)	−0.0076 (5)	0.0002 (5)
C4	0.0353 (6)	0.0369 (6)	0.0306 (6)	−0.0026 (5)	−0.0017 (5)	−0.0002 (5)
C5	0.0304 (6)	0.0282 (6)	0.0314 (6)	−0.0022 (4)	−0.0003 (5)	0.0018 (5)
C6	0.0336 (6)	0.0339 (6)	0.0293 (6)	−0.0018 (5)	0.0036 (5)	−0.0005 (5)
C7	0.0273 (6)	0.0341 (6)	0.0355 (6)	−0.0011 (5)	0.0049 (5)	0.0007 (5)
C8	0.0251 (5)	0.0285 (6)	0.0341 (6)	−0.0025 (4)	−0.0020 (5)	0.0018 (5)
C9	0.0272 (6)	0.0263 (5)	0.0306 (6)	−0.0013 (4)	0.0002 (4)	0.0015 (4)
C10	0.0268 (6)	0.0253 (5)	0.0315 (6)	−0.0017 (4)	−0.0003 (5)	0.0018 (4)
C11	0.0220 (5)	0.0339 (6)	0.0342 (6)	−0.0036 (4)	−0.0012 (4)	0.0032 (5)
C12	0.0262 (5)	0.0357 (6)	0.0327 (6)	−0.0013 (5)	−0.0007 (5)	−0.0002 (5)
C13	0.0313 (6)	0.0391 (6)	0.0336 (6)	−0.0008 (5)	0.0017 (5)	0.0034 (5)
C14	0.0416 (7)	0.0362 (7)	0.0456 (8)	0.0045 (5)	0.0010 (6)	0.0053 (6)
C15	0.0448 (7)	0.0427 (7)	0.0473 (8)	0.0099 (6)	0.0079 (6)	−0.0024 (6)
C16	0.0506 (8)	0.0490 (8)	0.0381 (7)	0.0056 (6)	0.0135 (6)	0.0035 (6)
C17	0.0434 (7)	0.0385 (7)	0.0365 (7)	0.0025 (6)	0.0052 (5)	0.0059 (5)
C18	0.0226 (5)	0.0341 (6)	0.0350 (6)	−0.0024 (5)	0.0007 (4)	−0.0031 (5)
C19	0.0242 (5)	0.0474 (7)	0.0297 (6)	0.0033 (5)	0.0016 (5)	−0.0009 (5)
C20	0.0350 (7)	0.0671 (9)	0.0369 (7)	−0.0055 (6)	−0.0015 (5)	−0.0040 (6)
C21	0.0428 (8)	0.1077 (15)	0.0349 (8)	−0.0028 (9)	−0.0077 (6)	0.0057 (8)
C22	0.0429 (8)	0.0980 (14)	0.0459 (9)	0.0144 (9)	0.0010 (7)	0.0269 (9)
C23	0.0461 (8)	0.0589 (9)	0.0544 (9)	0.0169 (7)	0.0097 (7)	0.0183 (7)
C24	0.0376 (7)	0.0449 (7)	0.0399 (7)	0.0100 (6)	0.0025 (6)	0.0025 (6)
C25	0.0302 (6)	0.0365 (6)	0.0370 (7)	−0.0007 (5)	−0.0047 (5)	0.0026 (5)
C26	0.0290 (6)	0.0363 (6)	0.0341 (6)	−0.0001 (5)	−0.0040 (5)	−0.0017 (5)
C27	0.0387 (7)	0.0379 (7)	0.0451 (8)	0.0025 (5)	−0.0019 (6)	0.0017 (6)
C28	0.0380 (7)	0.0434 (7)	0.0498 (8)	0.0115 (6)	−0.0015 (6)	−0.0036 (6)
C29	0.0315 (7)	0.0573 (9)	0.0474 (8)	0.0065 (6)	0.0056 (6)	−0.0056 (7)
C30	0.0375 (7)	0.0528 (8)	0.0525 (8)	0.0019 (6)	0.0094 (6)	0.0090 (7)
C31	0.0340 (6)	0.0425 (7)	0.0457 (8)	0.0056 (5)	0.0009 (6)	0.0064 (6)
C32	0.0271 (6)	0.0347 (6)	0.0346 (6)	0.0008 (5)	0.0031 (5)	0.0003 (5)
C33	0.0254 (5)	0.0407 (6)	0.0321 (6)	0.0013 (5)	0.0021 (5)	−0.0013 (5)
C34	0.0341 (7)	0.0423 (7)	0.0536 (8)	0.0013 (6)	−0.0056 (6)	−0.0056 (6)
C35	0.0390 (7)	0.0568 (9)	0.0589 (9)	−0.0089 (6)	−0.0054 (7)	−0.0129 (7)
C36	0.0300 (6)	0.0806 (11)	0.0392 (7)	−0.0049 (7)	−0.0046 (6)	−0.0042 (7)
C37	0.0368 (7)	0.0674 (10)	0.0442 (8)	0.0065 (7)	−0.0061 (6)	0.0102 (7)
C38	0.0377 (7)	0.0447 (7)	0.0434 (8)	0.0018 (6)	−0.0033 (6)	0.0049 (6)

O1—C11	1.2184 (14)	C18—C19	1.4890 (17)
O2—C18	1.2178 (15)	C19—C24	1.3886 (19)
O3—C25	1.3760 (14)	C19—C20	1.3917 (18)
O3—C2	1.4027 (14)	C20—C21	1.386 (2)
O4—C25	1.1984 (15)	C20—H20	0.9500
O5—C32	1.3649 (14)	C21—C22	1.375 (3)
O5—C8	1.4019 (13)	C21—H21	0.9500
O6—C32	1.1994 (15)	C22—C23	1.384 (2)
C1—C2	1.3751 (16)	C22—H22	0.9500
C1—C10	1.4388 (16)	C23—C24	1.3839 (19)
C1—C11	1.5027 (17)	C23—H23	0.9500
C2—C3	1.4035 (18)	C24—H24	0.9500
C3—C4	1.3588 (17)	C25—C26	1.4796 (17)
C3—H3	0.9500	C26—C31	1.3866 (18)
C4—C5	1.4155 (17)	C26—C27	1.3900 (17)
C4—H4	0.9500	C27—C28	1.3817 (19)
C5—C6	1.4163 (16)	C27—H27	0.9500
C5—C10	1.4226 (17)	C28—C29	1.377 (2)
C6—C7	1.3582 (17)	C28—H28	0.9500
C6—H6	0.9500	C29—C30	1.384 (2)
C7—C8	1.4013 (17)	C29—H29	0.9500
C7—H7	0.9500	C30—C31	1.3859 (19)
C8—C9	1.3738 (16)	C30—H30	0.9500
C9—C10	1.4376 (16)	C31—H31	0.9500
C9—C18	1.5129 (16)	C32—C33	1.4845 (17)
C11—C12	1.4817 (16)	C33—C38	1.3859 (18)
C12—C13	1.3935 (17)	C33—C34	1.3892 (18)
C12—C17	1.3946 (17)	C34—C35	1.3835 (19)
C13—C14	1.3797 (18)	C34—H34	0.9500
C13—H13	0.9500	C35—C36	1.381 (2)
C14—C15	1.386 (2)	C35—H35	0.9500
C14—H14	0.9500	C36—C37	1.380 (2)
C15—C16	1.383 (2)	C36—H36	0.9500
C15—H15	0.9500	C37—C38	1.3848 (19)
C16—C17	1.3747 (19)	C37—H37	0.9500
C16—H16	0.9500	C38—H38	0.9500
C17—H17	0.9500
C25—O3—C2	116.55 (9)	C20—C19—C18	119.12 (12)
C32—O5—C8	117.77 (9)	C21—C20—C19	119.91 (15)
C2—C1—C10	118.47 (11)	C21—C20—H20	120.0
C2—C1—C11	119.67 (10)	C19—C20—H20	120.0
C10—C1—C11	121.09 (10)	C22—C21—C20	120.31 (15)
C1—C2—O3	118.21 (10)	C22—C21—H21	119.8
C1—C2—C3	123.37 (11)	C20—C21—H21	119.8
O3—C2—C3	118.07 (10)	C21—C22—C23	120.08 (15)
C4—C3—C2	118.65 (11)	C21—C22—H22	120.0
C4—C3—H3	120.7	C23—C22—H22	120.0
C2—C3—H3	120.7	C22—C23—C24	119.99 (16)
C3—C4—C5	121.25 (11)	C22—C23—H23	120.0
C3—C4—H4	119.4	C24—C23—H23	120.0
C5—C4—H4	119.4	C23—C24—C19	120.22 (14)
C4—C5—C6	119.70 (11)	C23—C24—H24	119.9
C4—C5—C10	120.09 (11)	C19—C24—H24	119.9
C6—C5—C10	120.20 (11)	O4—C25—O3	122.37 (11)
C7—C6—C5	121.31 (11)	O4—C25—C26	125.66 (11)
C7—C6—H6	119.3	O3—C25—C26	111.96 (10)
C5—C6—H6	119.3	C31—C26—C27	119.88 (12)
C6—C7—C8	118.32 (11)	C31—C26—C25	122.77 (11)
C6—C7—H7	120.8	C27—C26—C25	117.34 (11)
C8—C7—H7	120.8	C28—C27—C26	120.05 (13)
C9—C8—C7	123.71 (11)	C28—C27—H27	120.0
C9—C8—O5	117.25 (10)	C26—C27—H27	120.0
C7—C8—O5	118.57 (10)	C29—C28—C27	120.06 (12)
C8—C9—C10	118.45 (10)	C29—C28—H28	120.0
C8—C9—C18	116.39 (10)	C27—C28—H28	120.0
C10—C9—C18	124.56 (10)	C28—C29—C30	120.21 (12)
C5—C10—C9	117.92 (10)	C28—C29—H29	119.9
C5—C10—C1	118.17 (10)	C30—C29—H29	119.9
C9—C10—C1	123.91 (10)	C29—C30—C31	120.13 (13)
O1—C11—C12	120.84 (11)	C29—C30—H30	119.9
O1—C11—C1	118.09 (11)	C31—C30—H30	119.9
C12—C11—C1	121.05 (10)	C30—C31—C26	119.68 (12)
C13—C12—C17	119.17 (11)	C30—C31—H31	120.2
C13—C12—C11	122.38 (11)	C26—C31—H31	120.2
C17—C12—C11	118.45 (11)	O6—C32—O5	123.38 (11)
C14—C13—C12	120.30 (12)	O6—C32—C33	125.57 (11)
C14—C13—H13	119.9	O5—C32—C33	111.04 (10)
C12—C13—H13	119.9	C38—C33—C34	119.63 (12)
C13—C14—C15	120.03 (12)	C38—C33—C32	118.69 (11)
C13—C14—H14	120.0	C34—C33—C32	121.66 (11)
C15—C14—H14	120.0	C35—C34—C33	119.80 (13)
C16—C15—C14	119.88 (12)	C35—C34—H34	120.1
C16—C15—H15	120.1	C33—C34—H34	120.1
C14—C15—H15	120.1	C36—C35—C34	120.35 (14)
C17—C16—C15	120.40 (12)	C36—C35—H35	119.8
C17—C16—H16	119.8	C34—C35—H35	119.8
C15—C16—H16	119.8	C37—C36—C35	120.01 (13)
C16—C17—C12	120.22 (12)	C37—C36—H36	120.0
C16—C17—H17	119.9	C35—C36—H36	120.0
C12—C17—H17	119.9	C36—C37—C38	119.96 (14)
O2—C18—C19	121.95 (11)	C36—C37—H37	120.0
O2—C18—C9	118.98 (11)	C38—C37—H37	120.0
C19—C18—C9	118.96 (10)	C37—C38—C33	120.22 (13)
C24—C19—C20	119.42 (12)	C37—C38—H38	119.9
C24—C19—C18	121.43 (11)	C33—C38—H38	119.9
C10—C1—C2—O3	−174.10 (10)	C15—C16—C17—C12	−0.1 (2)
C11—C1—C2—O3	−4.11 (16)	C13—C12—C17—C16	−0.85 (19)
C10—C1—C2—C3	−0.96 (17)	C11—C12—C17—C16	−179.85 (12)
C11—C1—C2—C3	169.03 (11)	C8—C9—C18—O2	−111.05 (12)
C25—O3—C2—C1	−120.40 (12)	C10—C9—C18—O2	59.98 (15)
C25—O3—C2—C3	66.09 (14)	C8—C9—C18—C19	65.30 (14)
C1—C2—C3—C4	0.65 (19)	C10—C9—C18—C19	−123.68 (12)
O3—C2—C3—C4	173.80 (11)	O2—C18—C19—C24	−153.51 (12)
C2—C3—C4—C5	−0.25 (18)	C9—C18—C19—C24	30.26 (16)
C3—C4—C5—C6	−178.62 (11)	O2—C18—C19—C20	24.45 (17)
C3—C4—C5—C10	0.21 (18)	C9—C18—C19—C20	−151.78 (11)
C4—C5—C6—C7	177.65 (11)	C24—C19—C20—C21	−0.66 (19)
C10—C5—C6—C7	−1.18 (17)	C18—C19—C20—C21	−178.67 (12)
C5—C6—C7—C8	2.15 (17)	C19—C20—C21—C22	2.4 (2)
C6—C7—C8—C9	−0.37 (18)	C20—C21—C22—C23	−1.9 (2)
C6—C7—C8—O5	171.54 (10)	C21—C22—C23—C24	−0.4 (2)
C32—O5—C8—C9	−121.80 (11)	C22—C23—C24—C19	2.2 (2)
C32—O5—C8—C7	65.76 (13)	C20—C19—C24—C23	−1.64 (19)
C7—C8—C9—C10	−2.32 (17)	C18—C19—C24—C23	176.32 (11)
O5—C8—C9—C10	−174.33 (9)	C2—O3—C25—O4	2.77 (17)
C7—C8—C9—C18	169.28 (11)	C2—O3—C25—C26	−178.22 (10)
O5—C8—C9—C18	−2.73 (15)	O4—C25—C26—C31	−173.21 (13)
C4—C5—C10—C9	179.66 (10)	O3—C25—C26—C31	7.82 (17)
C6—C5—C10—C9	−1.52 (16)	O4—C25—C26—C27	5.6 (2)
C4—C5—C10—C1	−0.50 (16)	O3—C25—C26—C27	−173.33 (11)
C6—C5—C10—C1	178.32 (10)	C31—C26—C27—C28	0.3 (2)
C8—C9—C10—C5	3.17 (15)	C25—C26—C27—C28	−178.55 (12)
C18—C9—C10—C5	−167.69 (10)	C26—C27—C28—C29	0.0 (2)
C8—C9—C10—C1	−176.66 (11)	C27—C28—C29—C30	−0.3 (2)
C18—C9—C10—C1	12.48 (17)	C28—C29—C30—C31	0.2 (2)
C2—C1—C10—C5	0.86 (16)	C29—C30—C31—C26	0.2 (2)
C11—C1—C10—C5	−168.98 (10)	C27—C26—C31—C30	−0.4 (2)
C2—C1—C10—C9	−179.31 (10)	C25—C26—C31—C30	178.39 (13)
C11—C1—C10—C9	10.85 (17)	C8—O5—C32—O6	6.18 (17)
C2—C1—C11—O1	−121.04 (12)	C8—O5—C32—C33	−174.52 (9)
C10—C1—C11—O1	48.67 (15)	O6—C32—C33—C38	8.86 (19)
C2—C1—C11—C12	57.47 (15)	O5—C32—C33—C38	−170.42 (11)
C10—C1—C11—C12	−132.81 (11)	O6—C32—C33—C34	−169.72 (13)
O1—C11—C12—C13	−161.25 (11)	O5—C32—C33—C34	10.99 (16)
C1—C11—C12—C13	20.28 (17)	C38—C33—C34—C35	1.6 (2)
O1—C11—C12—C17	17.71 (17)	C32—C33—C34—C35	−179.88 (13)
C1—C11—C12—C17	−160.76 (11)	C33—C34—C35—C36	−0.7 (2)
C17—C12—C13—C14	1.15 (18)	C34—C35—C36—C37	−0.8 (2)
C11—C12—C13—C14	−179.89 (11)	C35—C36—C37—C38	1.6 (2)
C12—C13—C14—C15	−0.6 (2)	C36—C37—C38—C33	−0.7 (2)
C13—C14—C15—C16	−0.4 (2)	C34—C33—C38—C37	−0.8 (2)
C14—C15—C16—C17	0.7 (2)	C32—C33—C38—C37	−179.42 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···O1i	0.95	2.41	3.0584 (17)	125
C28—H28···Cg2i	0.95	2.65	3.4877 (14)	148

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C5–C10 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15⋯O1i	0.95	2.41	3.0584 (17)	125
C28—H28⋯Cg2i	0.95	2.65	3.4877 (14)	148

Symmetry code: (i) .