2,7-Dimeth-oxy-1,8-bis-(4-phen-oxy-benzo-yl)naphthalene.

In the title mol-ecule {systematic name: [2,7-dimethoxy-8-(4-phenoxybenzoyl)naphthalen-1-yl](4-phenoxyphenyl)methan-one}, C(38)H(28)O(6), the 4-phen-oxy-benzoyl units adopt a syn orientation with respect to the naphthalene ring system. The inter-nal benzene rings, A and B, make dihedral angles of 86.72 (5) and 79.22 (5)° with the naphthalene ring system. The two terminal benzene rings, C and D, of the 4-phen-oxy-benzoyl groups are twisted with respect to benzene rings A and B, with dihedral angles of A/C = 62.72 (8) and B/D = 87.61 (6)°. In the crystal, H atoms in the naphthalene system make two types of inter-molecular C-H⋯O inter-actions with the carbonyl O atom and the phenyl etheral O atom of neighbouring mol-ecules. Mol-ecules are further linked by C-H⋯π inter-actions involving a H atom of terminal benzene ring D and the π-system of the inter-nal benzene ring A, forming dimers centered about an inversion center.

Related literature

For the syntheses of aroylated naphthalene compounds via electrophilic aromatic substitution of naphthalene derivatives, see: Okamoto & Yonezawa (2009 ▶). For the structures of closely related compounds, see: Nakaema et al. (2007 ▶, 2008 ▶); Mitsui et al. (2010 ▶); Muto et al. (2010 ▶); Watanabe et al. (2010 ▶).

Experimental

Crystal data

C38H28O6

M = 580.60

Monoclinic,

a = 12.0733 (4) Å

b = 12.4806 (4) Å

c = 19.8094 (6) Å

β = 91.115 (2)°

V = 2984.36 (15) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 193 K

0.50 × 0.30 × 0.30 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.720, T max = 0.816

54106 measured reflections

5458 independent reflections

4862 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.099

S = 1.04

5458 reflections

400 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.13 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); 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 datablocks I, global. DOI: 10.1107/S1600536810042170/su2217sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042170/su2217Isup2.hkl

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

C38H28O6	F(000) = 1216
Mr = 580.60	Dx = 1.292 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2yn	Cell parameters from 37382 reflections
a = 12.0733 (4) Å	θ = 3.5–68.3°
b = 12.4806 (4) Å	µ = 0.71 mm−1
c = 19.8094 (6) Å	T = 193 K
β = 91.115 (2)°	Block, yellow
V = 2984.36 (15) Å3	0.50 × 0.30 × 0.30 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	5458 independent reflections
Radiation source: rotating anode	4862 reflections with I > 2σ(I)
graphite	Rint = 0.038
Detector resolution: 10.00 pixels mm-1	θmax = 68.3°, θmin = 4.2°
ω scans	h = −14→14
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −15→15
Tmin = 0.720, Tmax = 0.816	l = −23→23
54106 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) = 0.099	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.5589P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.001
5458 reflections	Δρmax = 0.16 e Å−3
400 parameters	Δρmin = −0.13 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: 0.00337 (19)

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	0.96053 (8)	0.06684 (7)	0.81736 (5)	0.0546 (2)
O2	0.77701 (9)	−0.00287 (7)	0.90988 (5)	0.0586 (3)
O3	0.97983 (8)	0.27793 (8)	0.73618 (5)	0.0584 (3)
O4	0.51924 (8)	0.06935 (9)	0.91941 (5)	0.0615 (3)
O5	1.08799 (8)	0.36651 (9)	1.06682 (5)	0.0620 (3)
O6	0.79851 (8)	0.28865 (8)	1.16825 (4)	0.0556 (3)
C1	0.83140 (10)	0.20657 (9)	0.79447 (6)	0.0406 (3)
C2	0.86712 (11)	0.27048 (10)	0.74219 (6)	0.0471 (3)
C3	0.79253 (12)	0.32401 (11)	0.69846 (7)	0.0522 (3)
H3	0.8189	0.3692	0.6637	0.063*
C4	0.68212 (12)	0.30989 (11)	0.70687 (6)	0.0510 (3)
H4	0.6314	0.3447	0.6769	0.061*
C5	0.64066 (10)	0.24509 (10)	0.75887 (6)	0.0447 (3)
C6	0.52610 (11)	0.22967 (12)	0.76518 (7)	0.0542 (3)
H6	0.4772	0.2613	0.7328	0.065*
C7	0.48293 (11)	0.17099 (13)	0.81612 (7)	0.0579 (4)
H7	0.4053	0.1600	0.8186	0.069*
C8	0.55556 (11)	0.12678 (11)	0.86504 (7)	0.0493 (3)
C9	0.66870 (10)	0.13650 (9)	0.86044 (6)	0.0408 (3)
C10	0.71611 (10)	0.19418 (9)	0.80557 (6)	0.0394 (3)
C11	0.92353 (10)	0.15289 (9)	0.83493 (6)	0.0405 (3)
C12	0.96973 (9)	0.21139 (9)	0.89451 (6)	0.0388 (3)
C13	0.92476 (9)	0.30783 (9)	0.91570 (6)	0.0407 (3)
H13	0.8647	0.3388	0.8909	0.049*
C14	0.96670 (10)	0.35918 (10)	0.97258 (6)	0.0446 (3)
H14	0.9354	0.4250	0.9870	0.054*
C15	1.05418 (10)	0.31414 (11)	1.00819 (6)	0.0478 (3)
C16	1.10038 (11)	0.21766 (11)	0.98832 (7)	0.0535 (3)
H16	1.1600	0.1867	1.0135	0.064*
C17	1.05836 (11)	0.16749 (10)	0.93132 (7)	0.0477 (3)
H17	1.0903	0.1020	0.9169	0.057*
C18	1.19700 (12)	0.39961 (11)	1.07515 (7)	0.0522 (3)
C19	1.27352 (14)	0.39668 (15)	1.02490 (8)	0.0715 (4)
H19	1.2535	0.3709	0.9812	0.086*
C20	1.38027 (17)	0.4318 (2)	1.03878 (11)	0.0967 (7)
H20	1.4343	0.4283	1.0046	0.116*
C21	1.40910 (18)	0.47185 (18)	1.10142 (11)	0.0946 (6)
H21	1.4825	0.4962	1.1105	0.113*
C22	1.33065 (17)	0.47633 (14)	1.15093 (9)	0.0758 (5)
H22	1.3501	0.5042	1.1942	0.091*
C23	1.22396 (14)	0.44059 (11)	1.13820 (7)	0.0602 (4)
H23	1.1699	0.4441	1.1723	0.072*
C24	0.73586 (10)	0.08501 (9)	0.91703 (6)	0.0412 (3)
C25	0.74864 (9)	0.14370 (9)	0.98181 (6)	0.0388 (3)
C26	0.69332 (10)	0.23842 (10)	0.99588 (6)	0.0423 (3)
H26	0.6442	0.2685	0.9629	0.051*
C27	0.70890 (10)	0.28958 (11)	1.05731 (6)	0.0458 (3)
H27	0.6706	0.3542	1.0667	0.055*
C28	0.78094 (10)	0.24554 (10)	1.10496 (6)	0.0441 (3)
C29	0.83819 (11)	0.15178 (10)	1.09148 (6)	0.0487 (3)
H29	0.8880	0.1224	1.1242	0.058*
C30	0.82200 (11)	0.10197 (10)	1.03023 (6)	0.0461 (3)
H30	0.8614	0.0380	1.0207	0.055*
C31	0.77444 (11)	0.39731 (11)	1.17747 (6)	0.0477 (3)
C32	0.68244 (12)	0.42435 (12)	1.21339 (7)	0.0569 (4)
H32	0.6344	0.3705	1.2300	0.068*
C33	0.66113 (13)	0.53178 (13)	1.22497 (8)	0.0651 (4)
H33	0.5974	0.5521	1.2493	0.078*
C34	0.73172 (13)	0.60918 (13)	1.20139 (8)	0.0637 (4)
H34	0.7169	0.6827	1.2097	0.076*
C35	0.82377 (13)	0.58022 (13)	1.16573 (8)	0.0625 (4)
H35	0.8722	0.6339	1.1494	0.075*
C36	0.84602 (12)	0.47327 (12)	1.15348 (7)	0.0561 (3)
H36	0.9095	0.4528	1.1290	0.067*
C37	1.02198 (14)	0.34475 (15)	0.68454 (9)	0.0741 (5)
H37A	1.1031	0.3439	0.6867	0.089*
H37B	0.9955	0.4182	0.6909	0.089*
H37C	0.9964	0.3182	0.6404	0.089*
C38	0.40630 (15)	0.0786 (2)	0.93694 (12)	0.1008 (7)
H38A	0.3948	0.0437	0.9806	0.121*
H38B	0.3598	0.0439	0.9023	0.121*
H38C	0.3863	0.1545	0.9401	0.121*

	U11	U22	U33	U12	U13	U23
O1	0.0598 (6)	0.0431 (5)	0.0604 (6)	0.0113 (4)	−0.0108 (4)	−0.0065 (4)
O2	0.0817 (7)	0.0420 (5)	0.0514 (5)	0.0130 (5)	−0.0147 (5)	−0.0058 (4)
O3	0.0499 (5)	0.0617 (6)	0.0636 (6)	0.0012 (4)	0.0039 (4)	0.0206 (5)
O4	0.0488 (5)	0.0698 (7)	0.0658 (6)	−0.0101 (5)	0.0012 (4)	0.0149 (5)
O5	0.0549 (6)	0.0761 (7)	0.0546 (6)	−0.0006 (5)	−0.0087 (4)	−0.0167 (5)
O6	0.0719 (6)	0.0533 (6)	0.0411 (5)	0.0076 (5)	−0.0123 (4)	−0.0064 (4)
C1	0.0459 (6)	0.0357 (6)	0.0399 (6)	0.0017 (5)	−0.0052 (5)	0.0007 (5)
C2	0.0492 (7)	0.0438 (7)	0.0481 (7)	0.0032 (5)	−0.0007 (5)	0.0045 (5)
C3	0.0610 (8)	0.0491 (8)	0.0462 (7)	0.0042 (6)	−0.0033 (6)	0.0116 (6)
C4	0.0593 (8)	0.0491 (7)	0.0440 (7)	0.0091 (6)	−0.0120 (6)	0.0050 (6)
C5	0.0491 (7)	0.0430 (7)	0.0414 (6)	0.0049 (5)	−0.0106 (5)	−0.0018 (5)
C6	0.0494 (7)	0.0581 (8)	0.0545 (8)	0.0052 (6)	−0.0163 (6)	0.0021 (6)
C7	0.0407 (7)	0.0666 (9)	0.0660 (9)	−0.0031 (6)	−0.0106 (6)	0.0031 (7)
C8	0.0481 (7)	0.0477 (7)	0.0519 (7)	−0.0055 (6)	−0.0038 (6)	0.0015 (6)
C9	0.0445 (6)	0.0374 (6)	0.0400 (6)	−0.0013 (5)	−0.0073 (5)	−0.0025 (5)
C10	0.0452 (6)	0.0351 (6)	0.0377 (6)	0.0013 (5)	−0.0081 (5)	−0.0038 (5)
C11	0.0411 (6)	0.0356 (6)	0.0448 (6)	0.0009 (5)	−0.0015 (5)	0.0042 (5)
C12	0.0381 (6)	0.0349 (6)	0.0433 (6)	−0.0012 (5)	−0.0016 (5)	0.0054 (5)
C13	0.0369 (6)	0.0359 (6)	0.0492 (7)	−0.0001 (5)	−0.0035 (5)	0.0058 (5)
C14	0.0423 (6)	0.0381 (6)	0.0535 (7)	−0.0013 (5)	0.0008 (5)	−0.0017 (5)
C15	0.0455 (7)	0.0513 (7)	0.0465 (7)	−0.0035 (6)	−0.0041 (5)	−0.0029 (6)
C16	0.0509 (7)	0.0552 (8)	0.0537 (8)	0.0085 (6)	−0.0150 (6)	0.0020 (6)
C17	0.0497 (7)	0.0411 (7)	0.0521 (7)	0.0088 (5)	−0.0073 (6)	0.0027 (5)
C18	0.0560 (8)	0.0464 (7)	0.0534 (7)	0.0011 (6)	−0.0158 (6)	0.0014 (6)
C19	0.0657 (10)	0.0865 (12)	0.0619 (9)	−0.0152 (8)	−0.0117 (7)	−0.0112 (8)
C20	0.0701 (11)	0.1271 (18)	0.0927 (14)	−0.0304 (12)	−0.0038 (10)	−0.0231 (13)
C21	0.0769 (12)	0.1078 (16)	0.0979 (15)	−0.0283 (11)	−0.0281 (11)	−0.0112 (12)
C22	0.0966 (13)	0.0629 (10)	0.0665 (10)	−0.0146 (9)	−0.0363 (10)	−0.0002 (8)
C23	0.0814 (10)	0.0475 (8)	0.0508 (8)	−0.0021 (7)	−0.0179 (7)	0.0023 (6)
C24	0.0459 (6)	0.0358 (6)	0.0418 (6)	−0.0033 (5)	−0.0029 (5)	0.0021 (5)
C25	0.0422 (6)	0.0348 (6)	0.0392 (6)	−0.0049 (5)	−0.0026 (5)	0.0039 (5)
C26	0.0403 (6)	0.0453 (7)	0.0411 (6)	0.0026 (5)	−0.0060 (5)	0.0010 (5)
C27	0.0447 (6)	0.0462 (7)	0.0464 (7)	0.0065 (5)	−0.0040 (5)	−0.0048 (5)
C28	0.0478 (7)	0.0461 (7)	0.0382 (6)	−0.0042 (5)	−0.0034 (5)	−0.0021 (5)
C29	0.0580 (8)	0.0434 (7)	0.0441 (7)	0.0031 (6)	−0.0138 (6)	0.0043 (5)
C30	0.0567 (7)	0.0348 (6)	0.0463 (7)	0.0020 (5)	−0.0076 (5)	0.0034 (5)
C31	0.0519 (7)	0.0522 (8)	0.0387 (6)	−0.0001 (6)	−0.0077 (5)	−0.0075 (5)
C32	0.0554 (8)	0.0596 (9)	0.0558 (8)	−0.0123 (7)	0.0045 (6)	−0.0102 (7)
C33	0.0582 (8)	0.0671 (10)	0.0706 (10)	−0.0053 (7)	0.0151 (7)	−0.0195 (8)
C34	0.0663 (9)	0.0533 (8)	0.0719 (10)	−0.0056 (7)	0.0077 (7)	−0.0161 (7)
C35	0.0629 (9)	0.0602 (9)	0.0646 (9)	−0.0141 (7)	0.0077 (7)	−0.0052 (7)
C36	0.0517 (8)	0.0661 (9)	0.0506 (7)	−0.0023 (7)	0.0063 (6)	−0.0075 (7)
C37	0.0649 (9)	0.0804 (11)	0.0774 (11)	0.0013 (8)	0.0147 (8)	0.0301 (9)
C38	0.0584 (10)	0.1314 (19)	0.1134 (16)	−0.0008 (11)	0.0215 (10)	0.0495 (14)

O1—C11	1.2167 (14)	C18—C23	1.3826 (19)
O2—C24	1.2135 (15)	C19—C20	1.384 (2)
O3—C2	1.3714 (16)	C19—H19	0.9500
O3—C37	1.4217 (17)	C20—C21	1.376 (3)
O4—C8	1.3727 (16)	C20—H20	0.9500
O4—C38	1.418 (2)	C21—C22	1.378 (3)
O5—C18	1.3863 (17)	C21—H21	0.9500
O5—C15	1.3871 (15)	C22—C23	1.382 (2)
O6—C28	1.3771 (14)	C22—H22	0.9500
O6—C31	1.3996 (16)	C23—H23	0.9500
C1—C2	1.3829 (17)	C24—C25	1.4832 (16)
C1—C10	1.4219 (17)	C25—C26	1.3887 (17)
C1—C11	1.5145 (16)	C25—C30	1.3938 (16)
C2—C3	1.4061 (18)	C26—C27	1.3839 (17)
C3—C4	1.358 (2)	C26—H26	0.9500
C3—H3	0.9500	C27—C28	1.3847 (17)
C4—C5	1.4092 (19)	C27—H27	0.9500
C4—H4	0.9500	C28—C29	1.3877 (18)
C5—C6	1.4045 (19)	C29—C30	1.3738 (18)
C5—C10	1.4339 (16)	C29—H29	0.9500
C6—C7	1.359 (2)	C30—H30	0.9500
C6—H6	0.9500	C31—C32	1.3729 (19)
C7—C8	1.4070 (19)	C31—C36	1.374 (2)
C7—H7	0.9500	C32—C33	1.385 (2)
C8—C9	1.3761 (17)	C32—H32	0.9500
C9—C10	1.4323 (17)	C33—C34	1.376 (2)
C9—C24	1.5139 (16)	C33—H33	0.9500
C11—C12	1.4871 (16)	C34—C35	1.377 (2)
C12—C13	1.3887 (17)	C34—H34	0.9500
C12—C17	1.3952 (16)	C35—C36	1.384 (2)
C13—C14	1.3838 (17)	C35—H35	0.9500
C13—H13	0.9500	C36—H36	0.9500
C14—C15	1.3783 (18)	C37—H37A	0.9800
C14—H14	0.9500	C37—H37B	0.9800
C15—C16	1.3873 (19)	C37—H37C	0.9800
C16—C17	1.3792 (18)	C38—H38A	0.9800
C16—H16	0.9500	C38—H38B	0.9800
C17—H17	0.9500	C38—H38C	0.9800
C18—C19	1.372 (2)
C2—O3—C37	118.15 (11)	C21—C20—H20	119.6
C8—O4—C38	118.24 (12)	C19—C20—H20	119.6
C18—O5—C15	120.22 (11)	C20—C21—C22	119.42 (18)
C28—O6—C31	117.95 (10)	C20—C21—H21	120.3
C2—C1—C10	119.93 (11)	C22—C21—H21	120.3
C2—C1—C11	114.52 (11)	C21—C22—C23	120.55 (16)
C10—C1—C11	125.54 (10)	C21—C22—H22	119.7
O3—C2—C1	115.37 (11)	C23—C22—H22	119.7
O3—C2—C3	122.61 (12)	C22—C23—C18	119.11 (17)
C1—C2—C3	122.01 (12)	C22—C23—H23	120.4
C4—C3—C2	118.77 (12)	C18—C23—H23	120.4
C4—C3—H3	120.6	O2—C24—C25	120.76 (11)
C2—C3—H3	120.6	O2—C24—C9	120.79 (11)
C3—C4—C5	121.84 (12)	C25—C24—C9	118.44 (10)
C3—C4—H4	119.1	C26—C25—C30	118.80 (11)
C5—C4—H4	119.1	C26—C25—C24	123.49 (10)
C6—C5—C4	120.53 (11)	C30—C25—C24	117.70 (11)
C6—C5—C10	119.75 (12)	C27—C26—C25	120.77 (11)
C4—C5—C10	119.71 (12)	C27—C26—H26	119.6
C7—C6—C5	122.17 (12)	C25—C26—H26	119.6
C7—C6—H6	118.9	C26—C27—C28	119.28 (12)
C5—C6—H6	118.9	C26—C27—H27	120.4
C6—C7—C8	118.68 (13)	C28—C27—H27	120.4
C6—C7—H7	120.7	O6—C28—C27	123.30 (11)
C8—C7—H7	120.7	O6—C28—C29	115.86 (11)
O4—C8—C9	115.52 (11)	C27—C28—C29	120.81 (11)
O4—C8—C7	122.74 (12)	C30—C29—C28	119.26 (11)
C9—C8—C7	121.73 (12)	C30—C29—H29	120.4
C8—C9—C10	120.43 (11)	C28—C29—H29	120.4
C8—C9—C24	115.57 (11)	C29—C30—C25	121.08 (12)
C10—C9—C24	124.00 (10)	C29—C30—H30	119.5
C1—C10—C9	125.36 (10)	C25—C30—H30	119.5
C1—C10—C5	117.62 (11)	C32—C31—C36	122.03 (13)
C9—C10—C5	117.00 (11)	C32—C31—O6	118.55 (13)
O1—C11—C12	121.75 (11)	C36—C31—O6	119.34 (12)
O1—C11—C1	120.60 (11)	C31—C32—C33	118.59 (14)
C12—C11—C1	117.59 (10)	C31—C32—H32	120.7
C13—C12—C17	118.87 (11)	C33—C32—H32	120.7
C13—C12—C11	121.50 (10)	C34—C33—C32	120.34 (14)
C17—C12—C11	119.60 (11)	C34—C33—H33	119.8
C14—C13—C12	120.57 (11)	C32—C33—H33	119.8
C14—C13—H13	119.7	C35—C34—C33	120.08 (15)
C12—C13—H13	119.7	C35—C34—H34	120.0
C15—C14—C13	119.50 (12)	C33—C34—H34	120.0
C15—C14—H14	120.2	C34—C35—C36	120.31 (14)
C13—C14—H14	120.2	C34—C35—H35	119.8
C14—C15—O5	116.51 (12)	C36—C35—H35	119.8
C14—C15—C16	121.14 (12)	C31—C36—C35	118.64 (13)
O5—C15—C16	122.21 (12)	C31—C36—H36	120.7
C17—C16—C15	118.87 (12)	C35—C36—H36	120.7
C17—C16—H16	120.6	O3—C37—H37A	109.5
C15—C16—H16	120.6	O3—C37—H37B	109.5
C16—C17—C12	121.04 (12)	H37A—C37—H37B	109.5
C16—C17—H17	119.5	O3—C37—H37C	109.5
C12—C17—H17	119.5	H37A—C37—H37C	109.5
C19—C18—C23	121.03 (14)	H37B—C37—H37C	109.5
C19—C18—O5	123.84 (12)	O4—C38—H38A	109.5
C23—C18—O5	115.09 (13)	O4—C38—H38B	109.5
C18—C19—C20	119.02 (16)	H38A—C38—H38B	109.5
C18—C19—H19	120.5	O4—C38—H38C	109.5
C20—C19—H19	120.5	H38A—C38—H38C	109.5
C21—C20—C19	120.8 (2)	H38B—C38—H38C	109.5
C37—O3—C2—C1	−178.33 (13)	C18—O5—C15—C14	−123.87 (13)
C37—O3—C2—C3	1.6 (2)	C18—O5—C15—C16	60.33 (18)
C10—C1—C2—O3	179.42 (11)	C14—C15—C16—C17	0.9 (2)
C11—C1—C2—O3	−1.79 (16)	O5—C15—C16—C17	176.54 (12)
C10—C1—C2—C3	−0.50 (19)	C15—C16—C17—C12	−1.0 (2)
C11—C1—C2—C3	178.30 (12)	C13—C12—C17—C16	0.78 (19)
O3—C2—C3—C4	178.22 (12)	C11—C12—C17—C16	−177.51 (12)
C1—C2—C3—C4	−1.9 (2)	C15—O5—C18—C19	8.8 (2)
C2—C3—C4—C5	1.3 (2)	C15—O5—C18—C23	−173.45 (12)
C3—C4—C5—C6	−178.26 (13)	C23—C18—C19—C20	2.4 (3)
C3—C4—C5—C10	1.5 (2)	O5—C18—C19—C20	179.97 (17)
C4—C5—C6—C7	−177.53 (14)	C18—C19—C20—C21	−1.7 (3)
C10—C5—C6—C7	2.7 (2)	C19—C20—C21—C22	0.3 (4)
C5—C6—C7—C8	1.7 (2)	C20—C21—C22—C23	0.3 (3)
C38—O4—C8—C9	164.34 (16)	C21—C22—C23—C18	0.4 (3)
C38—O4—C8—C7	−17.1 (2)	C19—C18—C23—C22	−1.7 (2)
C6—C7—C8—O4	177.86 (13)	O5—C18—C23—C22	−179.52 (13)
C6—C7—C8—C9	−3.7 (2)	C8—C9—C24—O2	98.63 (15)
O4—C8—C9—C10	179.63 (11)	C10—C9—C24—O2	−82.66 (16)
C7—C8—C9—C10	1.0 (2)	C8—C9—C24—C25	−80.37 (14)
O4—C8—C9—C24	−1.60 (17)	C10—C9—C24—C25	98.34 (14)
C7—C8—C9—C24	179.81 (12)	O2—C24—C25—C26	−172.30 (12)
C2—C1—C10—C9	−175.50 (12)	C9—C24—C25—C26	6.70 (17)
C11—C1—C10—C9	5.84 (19)	O2—C24—C25—C30	9.04 (18)
C2—C1—C10—C5	3.26 (17)	C9—C24—C25—C30	−171.96 (11)
C11—C1—C10—C5	−175.39 (11)	C30—C25—C26—C27	−1.23 (18)
C8—C9—C10—C1	−177.92 (12)	C24—C25—C26—C27	−179.88 (11)
C24—C9—C10—C1	3.42 (19)	C25—C26—C27—C28	0.25 (19)
C8—C9—C10—C5	3.31 (17)	C31—O6—C28—C27	−22.47 (18)
C24—C9—C10—C5	−175.35 (11)	C31—O6—C28—C29	159.22 (12)
C6—C5—C10—C1	176.01 (11)	C26—C27—C28—O6	−177.55 (11)
C4—C5—C10—C1	−3.76 (17)	C26—C27—C28—C29	0.68 (19)
C6—C5—C10—C9	−5.12 (17)	O6—C28—C29—C30	177.76 (12)
C4—C5—C10—C9	175.10 (11)	C27—C28—C29—C30	−0.6 (2)
C2—C1—C11—O1	−87.22 (15)	C28—C29—C30—C25	−0.4 (2)
C10—C1—C11—O1	91.50 (16)	C26—C25—C30—C29	1.33 (19)
C2—C1—C11—C12	90.10 (13)	C24—C25—C30—C29	−179.95 (12)
C10—C1—C11—C12	−91.18 (14)	C28—O6—C31—C32	107.42 (14)
O1—C11—C12—C13	−177.79 (11)	C28—O6—C31—C36	−75.86 (15)
C1—C11—C12—C13	4.92 (16)	C36—C31—C32—C33	0.7 (2)
O1—C11—C12—C17	0.44 (18)	O6—C31—C32—C33	177.33 (13)
C1—C11—C12—C17	−176.85 (11)	C31—C32—C33—C34	−0.7 (2)
C17—C12—C13—C14	−0.39 (18)	C32—C33—C34—C35	0.4 (3)
C11—C12—C13—C14	177.86 (11)	C33—C34—C35—C36	−0.1 (2)
C12—C13—C14—C15	0.28 (18)	C32—C31—C36—C35	−0.4 (2)
C13—C14—C15—O5	−176.41 (11)	O6—C31—C36—C35	−177.04 (12)
C13—C14—C15—C16	−0.6 (2)	C34—C35—C36—C31	0.1 (2)

Cg3 is the centroid of ring A (C12–C17).

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2i	0.95	2.44	3.1479 (17)	131
C6—H6···O6ii	0.95	2.56	3.3293 (16)	138
C35—H35···Cg3iii	0.95	2.78	3.6528 (17)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of ring A (C12–C17).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2i	0.95	2.44	3.1479 (17)	131
C6—H6⋯O6ii	0.95	2.56	3.3293 (16)	138
C35—H35⋯Cg3iii	0.95	2.78	3.6528 (17)	153

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