[2,7-Dimeth-oxy-8-(4-propyl-benzo-yl)naphthalen-1-yl](4-propyl-phen-yl)methanone.

In the title compound, C(32)H(32)O(4), the 4-propyl-benzoyl groups at the 1- and 8-positions of the naphthalene ring system are aligned almost anti-parallel, and their benzene rings make a dihedral angle of 8.64 (10)°. The dihedral angles between the naphthalene ring system and the benzene rings are 69.37 (8) and 69.45 (8)°. In the crystal, C-H⋯O inter-actions link adjacent mol-ecules via their aroyl groups.

Related literature

For 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

C32H32O4

M = 480.58

Monoclinic,

a = 18.1224 (3) Å

b = 7.91914 (14) Å

c = 19.7355 (4) Å

β = 113.502 (1)°

V = 2597.37 (8) Å3

Z = 4

Cu Kα radiation

μ = 0.63 mm−1

T = 193 K

0.40 × 0.30 × 0.05 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.786, T max = 0.969

45013 measured reflections

4752 independent reflections

3258 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.152

S = 1.10

4752 reflections

330 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.26 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: Il Milione (Burla et al., 2007) ▶; program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: CrystalStructure (Rigaku, 2010 ▶); software used to prepare material for publication: CrystalStructure.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812033582/hb6909sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812033582/hb6909Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812033582/hb6909Isup3.cml

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

C32H32O4	F(000) = 1024
Mr = 480.58	Dx = 1.229 Mg m−3
Monoclinic, P21/n	Melting point = 448.9–447.1 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54187 Å
a = 18.1224 (3) Å	Cell parameters from 25236 reflections
b = 7.91914 (14) Å	θ = 4.3–68.2°
c = 19.7355 (4) Å	µ = 0.63 mm−1
β = 113.502 (1)°	T = 193 K
V = 2597.37 (8) Å3	Platelet, colorless
Z = 4	0.40 × 0.30 × 0.05 mm

Rigaku R-AXIS RAPID diffractometer	4752 independent reflections
Radiation source: rotating anode	3258 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 4.3°
ω scans	h = −21→21
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −9→9
Tmin = 0.786, Tmax = 0.969	l = −23→23
45013 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)] = 0.048	H-atom parameters constrained
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.0684P)2 + 0.7538P] where P = (Fo2 + 2Fc2)/3
S = 1.10	(Δ/σ)max < 0.001
4752 reflections	Δρmax = 0.22 e Å−3
330 parameters	Δρmin = −0.26 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: 0.0024 (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	0.24425 (9)	0.4558 (2)	0.71149 (8)	0.0569 (4)
O2	0.01824 (9)	0.1904 (2)	0.33799 (8)	0.0610 (4)
O3	0.27655 (8)	0.20263 (18)	0.58444 (8)	0.0532 (4)
O4	0.17938 (9)	0.44541 (18)	0.42987 (8)	0.0542 (4)
C1	0.03056 (14)	0.3547 (3)	0.61602 (12)	0.0540 (5)
H1	−0.0172	0.3500	0.6250	0.065*
C2	−0.04538 (13)	0.2496 (3)	0.49034 (13)	0.0535 (5)
H2	−0.0924	0.2435	0.5005	0.064*
C3	0.10007 (13)	0.4085 (3)	0.67087 (13)	0.0548 (5)
H3	0.1008	0.4425	0.7173	0.066*
C4	0.02756 (12)	0.3058 (3)	0.54627 (12)	0.0467 (5)
C5	−0.04981 (13)	0.2041 (3)	0.42247 (13)	0.0553 (6)
H5	−0.0989	0.1634	0.3860	0.066*
C6	0.17079 (12)	0.4131 (3)	0.65775 (11)	0.0467 (5)
C7	0.09867 (11)	0.3134 (2)	0.53196 (11)	0.0422 (5)
C8	0.01909 (12)	0.2179 (3)	0.40692 (12)	0.0499 (5)
C9	0.17178 (12)	0.3663 (2)	0.59093 (10)	0.0421 (5)
C10	0.09209 (12)	0.2697 (2)	0.45953 (11)	0.0436 (5)
C11	0.25296 (12)	0.3465 (3)	0.58720 (10)	0.0434 (5)
C12	0.27818 (12)	0.6589 (3)	0.59160 (11)	0.0478 (5)
H12	0.2277	0.6783	0.5944	0.057*
C13	0.32583 (13)	0.7945 (3)	0.59118 (12)	0.0534 (5)
H13	0.3076	0.9060	0.5935	0.064*
C14	0.30310 (11)	0.4946 (2)	0.58802 (10)	0.0423 (5)
C15	0.40005 (13)	0.7706 (3)	0.58743 (11)	0.0518 (5)
C16	0.37687 (12)	0.4698 (3)	0.58295 (11)	0.0507 (5)
H16	0.3947	0.3584	0.5797	0.061*
C17	0.42412 (13)	0.6057 (3)	0.58265 (12)	0.0551 (6)
H17	0.4742	0.5866	0.5791	0.066*
C18	0.45184 (15)	0.9209 (3)	0.58852 (13)	0.0658 (7)
H18A	0.4195	1.0017	0.5498	0.079*
H18B	0.4971	0.8825	0.5764	0.079*
C19	0.48555 (15)	1.0115 (3)	0.66281 (14)	0.0670 (7)
H19A	0.5152	1.1129	0.6584	0.080*
H19B	0.4401	1.0500	0.6747	0.080*
C20	0.54096 (15)	0.9046 (4)	0.72574 (14)	0.0726 (7)
H20A	0.5112	0.8074	0.7327	0.087*
H20B	0.5618	0.9721	0.7711	0.087*
H20C	0.5859	0.8648	0.7143	0.087*
C21	0.15938 (12)	0.2993 (3)	0.43450 (11)	0.0445 (5)
C22	0.17742 (13)	−0.0111 (3)	0.42097 (11)	0.0499 (5)
H22	0.1315	−0.0332	0.4315	0.060*
C23	0.20091 (12)	0.1545 (2)	0.41792 (10)	0.0436 (5)
C24	0.21995 (14)	−0.1447 (3)	0.40895 (12)	0.0546 (6)
H24	0.2023	−0.2570	0.4104	0.065*
C25	0.26860 (13)	0.1837 (3)	0.40237 (12)	0.0518 (5)
H25	0.2855	0.2960	0.3995	0.062*
C26	0.28793 (13)	−0.1169 (3)	0.39483 (11)	0.0521 (5)
C27	0.31099 (13)	0.0493 (3)	0.39115 (12)	0.0550 (6)
H27	0.3569	0.0709	0.3807	0.066*
C28	0.33506 (15)	−0.2620 (3)	0.38310 (12)	0.0611 (6)
H28A	0.3271	−0.3622	0.4094	0.073*
H28B	0.3930	−0.2330	0.4053	0.073*
C29	0.31187 (15)	−0.3071 (3)	0.30285 (13)	0.0644 (6)
H29A	0.3181	−0.2062	0.2760	0.077*
H29B	0.2545	−0.3408	0.2809	0.077*
C30	0.36266 (15)	−0.4497 (3)	0.29291 (14)	0.0688 (7)
H30A	0.4194	−0.4164	0.3139	0.083*
H30B	0.3457	−0.4739	0.2401	0.083*
H30C	0.3556	−0.5510	0.3182	0.083*
C31	0.24686 (15)	0.5212 (3)	0.77932 (12)	0.0656 (7)
H31A	0.2307	0.4331	0.8055	0.079*
H31B	0.2100	0.6173	0.7695	0.079*
H31C	0.3017	0.5583	0.8098	0.079*
C32	−0.04718 (15)	0.0998 (4)	0.28517 (13)	0.0715 (7)
H32A	−0.0550	−0.0062	0.3071	0.086*
H32B	−0.0355	0.0751	0.2418	0.086*
H32C	−0.0962	0.1682	0.2702	0.086*

	U11	U22	U33	U12	U13	U23
O1	0.0583 (9)	0.0656 (10)	0.0449 (8)	−0.0052 (7)	0.0187 (7)	−0.0098 (7)
O2	0.0540 (9)	0.0761 (11)	0.0463 (9)	−0.0106 (8)	0.0131 (7)	−0.0089 (7)
O3	0.0574 (9)	0.0405 (8)	0.0617 (9)	0.0069 (7)	0.0237 (7)	0.0021 (7)
O4	0.0629 (9)	0.0414 (9)	0.0585 (9)	−0.0071 (7)	0.0244 (7)	0.0017 (7)
C1	0.0569 (13)	0.0492 (13)	0.0615 (14)	0.0022 (10)	0.0296 (11)	0.0040 (10)
C2	0.0476 (12)	0.0511 (13)	0.0618 (14)	−0.0006 (10)	0.0220 (10)	0.0066 (10)
C3	0.0626 (14)	0.0517 (13)	0.0547 (13)	−0.0001 (11)	0.0285 (11)	−0.0031 (10)
C4	0.0485 (11)	0.0405 (11)	0.0531 (12)	0.0021 (9)	0.0224 (10)	0.0044 (9)
C5	0.0448 (11)	0.0547 (14)	0.0597 (14)	−0.0039 (10)	0.0137 (10)	0.0014 (11)
C6	0.0497 (11)	0.0410 (11)	0.0480 (11)	0.0003 (9)	0.0182 (9)	0.0004 (9)
C7	0.0427 (10)	0.0352 (11)	0.0476 (11)	0.0003 (8)	0.0166 (9)	0.0030 (8)
C8	0.0491 (12)	0.0489 (12)	0.0486 (12)	−0.0028 (10)	0.0163 (10)	0.0002 (9)
C9	0.0489 (11)	0.0343 (10)	0.0439 (10)	0.0009 (8)	0.0195 (9)	0.0016 (8)
C10	0.0454 (11)	0.0377 (11)	0.0458 (11)	−0.0014 (8)	0.0163 (9)	0.0016 (9)
C11	0.0481 (11)	0.0395 (11)	0.0398 (10)	0.0039 (9)	0.0145 (9)	0.0018 (8)
C12	0.0438 (11)	0.0430 (12)	0.0525 (12)	0.0015 (9)	0.0148 (9)	0.0006 (9)
C13	0.0523 (12)	0.0440 (12)	0.0600 (13)	−0.0038 (10)	0.0182 (10)	0.0002 (10)
C14	0.0404 (10)	0.0414 (11)	0.0406 (10)	0.0011 (8)	0.0113 (8)	0.0025 (8)
C15	0.0504 (12)	0.0553 (14)	0.0439 (11)	−0.0089 (10)	0.0125 (9)	0.0045 (10)
C16	0.0482 (12)	0.0520 (13)	0.0504 (12)	0.0060 (10)	0.0180 (9)	0.0043 (10)
C17	0.0440 (11)	0.0649 (15)	0.0549 (13)	−0.0014 (10)	0.0182 (10)	0.0059 (11)
C18	0.0593 (14)	0.0668 (16)	0.0628 (14)	−0.0163 (12)	0.0155 (11)	0.0118 (12)
C19	0.0604 (14)	0.0570 (15)	0.0795 (17)	−0.0157 (12)	0.0235 (13)	−0.0025 (13)
C20	0.0643 (15)	0.091 (2)	0.0588 (15)	−0.0128 (14)	0.0202 (12)	−0.0067 (14)
C21	0.0470 (11)	0.0405 (12)	0.0429 (11)	−0.0039 (9)	0.0146 (9)	0.0012 (9)
C22	0.0580 (13)	0.0446 (12)	0.0521 (12)	−0.0020 (10)	0.0273 (10)	0.0030 (9)
C23	0.0475 (11)	0.0427 (11)	0.0398 (10)	−0.0029 (9)	0.0165 (9)	0.0011 (8)
C24	0.0701 (15)	0.0437 (12)	0.0542 (13)	−0.0003 (11)	0.0292 (11)	0.0017 (10)
C25	0.0541 (12)	0.0493 (13)	0.0549 (13)	−0.0088 (10)	0.0246 (10)	−0.0023 (10)
C26	0.0566 (13)	0.0561 (14)	0.0413 (11)	0.0072 (10)	0.0173 (10)	0.0013 (9)
C27	0.0510 (12)	0.0631 (15)	0.0548 (13)	−0.0016 (11)	0.0251 (10)	−0.0034 (11)
C28	0.0656 (14)	0.0632 (15)	0.0531 (13)	0.0123 (12)	0.0221 (11)	0.0000 (11)
C29	0.0605 (14)	0.0694 (16)	0.0560 (14)	0.0108 (12)	0.0155 (11)	−0.0096 (12)
C30	0.0701 (16)	0.0726 (17)	0.0580 (14)	0.0131 (13)	0.0196 (12)	−0.0115 (12)
C31	0.0765 (16)	0.0654 (16)	0.0512 (13)	0.0056 (13)	0.0217 (12)	−0.0117 (11)
C32	0.0639 (15)	0.0814 (18)	0.0574 (14)	−0.0151 (13)	0.0117 (12)	−0.0142 (13)

O1—C6	1.373 (2)	C18—H18A	0.9900
O1—C31	1.418 (2)	C18—H18B	0.9900
O2—C8	1.372 (2)	C19—C20	1.507 (3)
O2—C32	1.422 (3)	C19—H19A	0.9900
O3—C11	1.226 (2)	C19—H19B	0.9900
O4—C21	1.226 (2)	C20—H20A	0.9800
C1—C3	1.361 (3)	C20—H20B	0.9800
C1—C4	1.410 (3)	C20—H20C	0.9800
C1—H1	0.9500	C21—C23	1.478 (3)
C2—C5	1.358 (3)	C22—C24	1.383 (3)
C2—C4	1.414 (3)	C22—C23	1.388 (3)
C2—H2	0.9500	C22—H22	0.9500
C3—C6	1.405 (3)	C23—C25	1.397 (3)
C3—H3	0.9500	C24—C26	1.385 (3)
C4—C7	1.426 (3)	C24—H24	0.9500
C5—C8	1.404 (3)	C25—C27	1.381 (3)
C5—H5	0.9500	C25—H25	0.9500
C6—C9	1.377 (3)	C26—C27	1.392 (3)
C7—C10	1.429 (3)	C26—C28	1.503 (3)
C7—C9	1.434 (3)	C27—H27	0.9500
C8—C10	1.379 (3)	C28—C29	1.511 (3)
C9—C11	1.510 (3)	C28—H28A	0.9900
C10—C21	1.506 (3)	C28—H28B	0.9900
C11—C14	1.480 (3)	C29—C30	1.518 (3)
C12—C13	1.380 (3)	C29—H29A	0.9900
C12—C14	1.389 (3)	C29—H29B	0.9900
C12—H12	0.9500	C30—H30A	0.9800
C13—C15	1.389 (3)	C30—H30B	0.9800
C13—H13	0.9500	C30—H30C	0.9800
C14—C16	1.394 (3)	C31—H31A	0.9800
C15—C17	1.392 (3)	C31—H31B	0.9800
C15—C18	1.511 (3)	C31—H31C	0.9800
C16—C17	1.377 (3)	C32—H32A	0.9800
C16—H16	0.9500	C32—H32B	0.9800
C17—H17	0.9500	C32—H32C	0.9800
C18—C19	1.524 (3)
C6—O1—C31	118.44 (17)	C18—C19—H19A	108.7
C8—O2—C32	118.93 (18)	C20—C19—H19B	108.7
C3—C1—C4	121.7 (2)	C18—C19—H19B	108.7
C3—C1—H1	119.1	H19A—C19—H19B	107.6
C4—C1—H1	119.1	C19—C20—H20A	109.5
C5—C2—C4	121.5 (2)	C19—C20—H20B	109.5
C5—C2—H2	119.3	H20A—C20—H20B	109.5
C4—C2—H2	119.3	C19—C20—H20C	109.5
C1—C3—C6	119.0 (2)	H20A—C20—H20C	109.5
C1—C3—H3	120.5	H20B—C20—H20C	109.5
C6—C3—H3	120.5	O4—C21—C23	121.58 (18)
C1—C4—C2	120.58 (19)	O4—C21—C10	118.27 (18)
C1—C4—C7	119.70 (19)	C23—C21—C10	120.13 (17)
C2—C4—C7	119.73 (19)	C24—C22—C23	120.90 (19)
C2—C5—C8	119.1 (2)	C24—C22—H22	119.6
C2—C5—H5	120.4	C23—C22—H22	119.6
C8—C5—H5	120.4	C22—C23—C25	118.49 (19)
O1—C6—C9	115.29 (18)	C22—C23—C21	122.13 (18)
O1—C6—C3	122.58 (19)	C25—C23—C21	119.29 (18)
C9—C6—C3	122.04 (19)	C22—C24—C26	121.0 (2)
C4—C7—C10	117.79 (18)	C22—C24—H24	119.5
C4—C7—C9	117.85 (18)	C26—C24—H24	119.5
C10—C7—C9	124.36 (17)	C27—C25—C23	120.1 (2)
O2—C8—C10	114.97 (18)	C27—C25—H25	120.0
O2—C8—C5	123.04 (19)	C23—C25—H25	120.0
C10—C8—C5	121.9 (2)	C24—C26—C27	118.0 (2)
C6—C9—C7	119.69 (18)	C24—C26—C28	121.0 (2)
C6—C9—C11	117.36 (17)	C27—C26—C28	120.9 (2)
C7—C9—C11	122.22 (17)	C25—C27—C26	121.5 (2)
C8—C10—C7	119.86 (18)	C25—C27—H27	119.3
C8—C10—C21	117.30 (18)	C26—C27—H27	119.3
C7—C10—C21	122.34 (17)	C26—C28—C29	113.86 (19)
O3—C11—C14	120.92 (18)	C26—C28—H28A	108.8
O3—C11—C9	117.53 (18)	C29—C28—H28A	108.8
C14—C11—C9	121.55 (17)	C26—C28—H28B	108.8
C13—C12—C14	120.78 (19)	C29—C28—H28B	108.8
C13—C12—H12	119.6	H28A—C28—H28B	107.7
C14—C12—H12	119.6	C28—C29—C30	112.45 (19)
C12—C13—C15	121.1 (2)	C28—C29—H29A	109.1
C12—C13—H13	119.5	C30—C29—H29A	109.1
C15—C13—H13	119.5	C28—C29—H29B	109.1
C12—C14—C16	118.47 (19)	C30—C29—H29B	109.1
C12—C14—C11	122.18 (18)	H29A—C29—H29B	107.8
C16—C14—C11	119.33 (18)	C29—C30—H30A	109.5
C13—C15—C17	117.9 (2)	C29—C30—H30B	109.5
C13—C15—C18	120.1 (2)	H30A—C30—H30B	109.5
C17—C15—C18	122.0 (2)	C29—C30—H30C	109.5
C17—C16—C14	120.4 (2)	H30A—C30—H30C	109.5
C17—C16—H16	119.8	H30B—C30—H30C	109.5
C14—C16—H16	119.8	O1—C31—H31A	109.5
C16—C17—C15	121.4 (2)	O1—C31—H31B	109.5
C16—C17—H17	119.3	H31A—C31—H31B	109.5
C15—C17—H17	119.3	O1—C31—H31C	109.5
C15—C18—C19	113.14 (19)	H31A—C31—H31C	109.5
C15—C18—H18A	109.0	H31B—C31—H31C	109.5
C19—C18—H18A	109.0	O2—C32—H32A	109.5
C15—C18—H18B	109.0	O2—C32—H32B	109.5
C19—C18—H18B	109.0	H32A—C32—H32B	109.5
H18A—C18—H18B	107.8	O2—C32—H32C	109.5
C20—C19—C18	114.1 (2)	H32A—C32—H32C	109.5
C20—C19—H19A	108.7	H32B—C32—H32C	109.5
C4—C1—C3—C6	−0.9 (3)	C14—C12—C13—C15	−0.2 (3)
C3—C1—C4—C2	179.7 (2)	C13—C12—C14—C16	−0.9 (3)
C3—C1—C4—C7	−0.5 (3)	C13—C12—C14—C11	−179.05 (19)
C5—C2—C4—C1	179.1 (2)	O3—C11—C14—C12	−179.58 (19)
C5—C2—C4—C7	−0.8 (3)	C9—C11—C14—C12	−0.6 (3)
C4—C2—C5—C8	−1.9 (3)	O3—C11—C14—C16	2.3 (3)
C31—O1—C6—C9	173.89 (19)	C9—C11—C14—C16	−178.71 (17)
C31—O1—C6—C3	−9.4 (3)	C12—C13—C15—C17	1.2 (3)
C1—C3—C6—O1	−175.9 (2)	C12—C13—C15—C18	−178.8 (2)
C1—C3—C6—C9	0.6 (3)	C12—C14—C16—C17	1.0 (3)
C1—C4—C7—C10	−177.32 (19)	C11—C14—C16—C17	179.17 (18)
C2—C4—C7—C10	2.5 (3)	C14—C16—C17—C15	0.1 (3)
C1—C4—C7—C9	2.0 (3)	C13—C15—C17—C16	−1.2 (3)
C2—C4—C7—C9	−178.17 (18)	C18—C15—C17—C16	178.9 (2)
C32—O2—C8—C10	165.2 (2)	C13—C15—C18—C19	68.8 (3)
C32—O2—C8—C5	−18.2 (3)	C17—C15—C18—C19	−111.2 (3)
C2—C5—C8—O2	−173.6 (2)	C15—C18—C19—C20	62.7 (3)
C2—C5—C8—C10	2.8 (3)	C8—C10—C21—O4	107.1 (2)
O1—C6—C9—C7	177.76 (17)	C7—C10—C21—O4	−64.8 (3)
C3—C6—C9—C7	1.0 (3)	C8—C10—C21—C23	−74.3 (2)
O1—C6—C9—C11	7.3 (3)	C7—C10—C21—C23	113.7 (2)
C3—C6—C9—C11	−169.44 (19)	C24—C22—C23—C25	0.0 (3)
C4—C7—C9—C6	−2.2 (3)	C24—C22—C23—C21	−176.60 (19)
C10—C7—C9—C6	177.02 (18)	O4—C21—C23—C22	−178.17 (19)
C4—C7—C9—C11	167.69 (17)	C10—C21—C23—C22	3.3 (3)
C10—C7—C9—C11	−13.1 (3)	O4—C21—C23—C25	5.2 (3)
O2—C8—C10—C7	175.68 (17)	C10—C21—C23—C25	−173.28 (18)
C5—C8—C10—C7	−1.0 (3)	C23—C22—C24—C26	1.1 (3)
O2—C8—C10—C21	3.5 (3)	C22—C23—C25—C27	−0.6 (3)
C5—C8—C10—C21	−173.08 (19)	C21—C23—C25—C27	176.10 (19)
C4—C7—C10—C8	−1.7 (3)	C22—C24—C26—C27	−1.7 (3)
C9—C7—C10—C8	179.06 (19)	C22—C24—C26—C28	178.9 (2)
C4—C7—C10—C21	170.04 (18)	C23—C25—C27—C26	0.1 (3)
C9—C7—C10—C21	−9.2 (3)	C24—C26—C27—C25	1.1 (3)
C6—C9—C11—O3	106.1 (2)	C28—C26—C27—C25	−179.5 (2)
C7—C9—C11—O3	−64.1 (3)	C24—C26—C28—C29	94.9 (3)
C6—C9—C11—C14	−73.0 (2)	C27—C26—C28—C29	−84.5 (3)
C7—C9—C11—C14	116.9 (2)	C26—C28—C29—C30	177.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O3i	0.95	2.41	3.342 (3)	168
C24—H24···O4ii	0.95	2.45	3.390 (3)	170

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O3i	0.95	2.41	3.342 (3)	168
C24—H24⋯O4ii	0.95	2.45	3.390 (3)	170

Symmetry codes: (i) ; (ii) .