1,2-Bis(benz-yloxy)-1,2-bis-(4-chloro-phen-yl)-3,8-dimeth-oxy-acenaphthene.

In the title compound, C(40)H(32)Cl(2)O(4), the two chloro-benzene rings are in syn orientations with respect to the naphthalene ring system and make dihedral angles of 57.12 (6) and 85.74 (6)° with it. The benzene rings of the benz-yloxy group make dihedral angles of 75.34 (6) and 83.95 (7)°, with the naphthalene ring system. In the crystal, the mol-ecules are linked by inter-molecular C-H⋯Cl inter-actions between the methyl-ene H atoms of the benz-yloxy group and the Cl atoms in adjacent mol-ecules. Furthermore, centrosymmetrically related mol-ecules are linked into dimeric units by pairs of C-H⋯π inter-actions.

Related literature

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

Experimental

Crystal data

C40H32Cl2O4

M = 647.56

Triclinic,

a = 10.9773 (2) Å

b = 12.6514 (2) Å

c = 12.9171 (2) Å

α = 102.387 (1)°

β = 104.899 (1)°

γ = 103.306 (1)°

V = 1614.04 (5) Å3

Z = 2

Cu Kα radiation

μ = 2.15 mm−1

T = 193 K

0.50 × 0.30 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi,1999 ▶) T min = 0.414, T max = 0.674

30622 measured reflections

5828 independent reflections

5503 reflections with I > 2σ(I)

R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.107

S = 1.06

5828 reflections

418 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.31 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 datablock(s) I, global. DOI: 10.1107/S1600536811035495/jh2320sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035495/jh2320Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035495/jh2320Isup3.cml

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

C40H32Cl2O4	Z = 2
Mr = 647.56	F(000) = 676
Triclinic, P1	Dx = 1.332 Mg m−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54187 Å
a = 10.9773 (2) Å	Cell parameters from 29110 reflections
b = 12.6514 (2) Å	θ = 3.7–68.2°
c = 12.9171 (2) Å	µ = 2.15 mm−1
α = 102.387 (1)°	T = 193 K
β = 104.899 (1)°	Block, colorless
γ = 103.306 (1)°	0.50 × 0.30 × 0.20 mm
V = 1614.04 (5) Å3

Rigaku R-AXIS RAPID diffractometer	5828 independent reflections
Radiation source: rotating anode	5503 reflections with I > 2σ(I)
graphite	Rint = 0.061
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.7°
ω scans	h = −13→12
Absorption correction: numerical (NUMABS; Higashi,1999)	k = −15→15
Tmin = 0.414, Tmax = 0.674	l = −15→15
30622 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)] = 0.037	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0623P)2 + 0.4586P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.002
5828 reflections	Δρmax = 0.43 e Å−3
418 parameters	Δρmin = −0.31 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: 0.0082 (4)

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
Cl1	1.11323 (4)	0.16739 (4)	0.15815 (4)	0.05437 (15)
Cl2	1.10086 (4)	0.63681 (3)	0.37022 (3)	0.04790 (14)
O1	0.49403 (9)	0.07269 (7)	0.17290 (8)	0.0276 (2)
O2	0.51556 (9)	0.25848 (8)	0.10705 (7)	0.0285 (2)
O3	0.70682 (12)	0.05722 (9)	0.43438 (9)	0.0405 (3)
O4	0.39937 (12)	0.43218 (10)	0.22526 (10)	0.0437 (3)
C1	0.59210 (13)	0.17780 (11)	0.36826 (11)	0.0283 (3)
C2	0.63214 (15)	0.12827 (12)	0.45074 (12)	0.0328 (3)
C3	0.59278 (17)	0.15073 (14)	0.54799 (12)	0.0397 (4)
H3	0.6227	0.1183	0.6059	0.048*
C4	0.51272 (17)	0.21801 (14)	0.55995 (13)	0.0413 (4)
H4	0.4864	0.2298	0.6250	0.050*
C5	0.46860 (15)	0.27021 (12)	0.47695 (12)	0.0354 (3)
C6	0.38935 (16)	0.34403 (13)	0.47836 (14)	0.0409 (4)
H6	0.3545	0.3588	0.5382	0.049*
C7	0.36209 (16)	0.39443 (13)	0.39523 (14)	0.0403 (4)
H7	0.3070	0.4423	0.3977	0.048*
C8	0.41422 (14)	0.37692 (12)	0.30514 (13)	0.0337 (3)
C9	0.48695 (13)	0.30165 (11)	0.29829 (11)	0.0284 (3)
C10	0.51254 (13)	0.24915 (11)	0.38316 (11)	0.0293 (3)
C11	0.60405 (13)	0.16494 (11)	0.25134 (10)	0.0256 (3)
C12	0.85295 (14)	0.19940 (12)	0.31986 (12)	0.0317 (3)
H12	0.8545	0.2269	0.3948	0.038*
C13	0.73237 (13)	0.15671 (11)	0.23323 (11)	0.0262 (3)
C14	0.97044 (14)	0.20211 (13)	0.29780 (13)	0.0367 (3)
H14	1.0524	0.2308	0.3570	0.044*
C15	0.96649 (14)	0.16232 (12)	0.18812 (13)	0.0347 (3)
C16	0.84865 (15)	0.11863 (12)	0.10077 (12)	0.0330 (3)
H16	0.8476	0.0912	0.0260	0.040*
C17	0.73205 (14)	0.11564 (12)	0.12420 (11)	0.0295 (3)
H17	0.6503	0.0850	0.0648	0.035*
C18	0.57022 (13)	0.27657 (11)	0.22371 (11)	0.0263 (3)
C19	0.69953 (13)	0.37403 (11)	0.26034 (11)	0.0270 (3)
C20	0.75744 (14)	0.44304 (11)	0.37078 (11)	0.0295 (3)
H20	0.7123	0.4341	0.4235	0.035*
C21	0.87998 (15)	0.52457 (12)	0.40500 (12)	0.0329 (3)
H21	0.9185	0.5711	0.4804	0.039*
C22	0.94520 (14)	0.53719 (12)	0.32793 (12)	0.0337 (3)
C23	0.88904 (15)	0.47151 (13)	0.21747 (12)	0.0358 (3)
H23	0.9340	0.4816	0.1649	0.043*
C24	0.76659 (14)	0.39090 (12)	0.18422 (12)	0.0319 (3)
H24	0.7275	0.3462	0.1081	0.038*
C25	0.77576 (19)	0.02741 (16)	0.52774 (14)	0.0494 (4)
H25A	0.8308	0.0966	0.5881	0.059*
H25B	0.8320	−0.0168	0.5052	0.059*
H25C	0.7119	−0.0181	0.5541	0.059*
C26	0.3045 (2)	0.49310 (18)	0.2163 (2)	0.0608 (5)
H26A	0.2179	0.4423	0.2075	0.073*
H26B	0.2984	0.5218	0.1511	0.073*
H26C	0.3319	0.5570	0.2842	0.073*
C27	0.49115 (14)	−0.03802 (11)	0.18391 (12)	0.0310 (3)
H27A	0.5499	−0.0313	0.2589	0.037*
H27B	0.5234	−0.0781	0.1270	0.037*
C28	0.35182 (14)	−0.10438 (11)	0.16839 (11)	0.0281 (3)
C29	0.26258 (15)	−0.05050 (13)	0.19605 (12)	0.0330 (3)
H29	0.2898	0.0298	0.2259	0.040*
C30	0.13410 (16)	−0.11310 (15)	0.18040 (13)	0.0405 (4)
H30	0.0738	−0.0754	0.1991	0.049*
C31	0.09343 (17)	−0.23016 (15)	0.13764 (15)	0.0476 (4)
H31	0.0054	−0.2729	0.1265	0.057*
C32	0.18202 (18)	−0.28417 (14)	0.11136 (15)	0.0476 (4)
H32	0.1549	−0.3646	0.0830	0.057*
C33	0.31026 (16)	−0.22221 (12)	0.12593 (13)	0.0366 (3)
H33	0.3700	−0.2604	0.1068	0.044*
C34	0.37626 (13)	0.20801 (12)	0.05308 (12)	0.0322 (3)
H34A	0.3278	0.2371	0.1019	0.039*
H34B	0.3530	0.1246	0.0382	0.039*
C35	0.33847 (13)	0.23730 (12)	−0.05534 (12)	0.0290 (3)
C36	0.23404 (15)	0.16125 (14)	−0.14550 (13)	0.0390 (3)
H36	0.1883	0.0911	−0.1383	0.047*
C37	0.19564 (18)	0.18624 (17)	−0.24597 (15)	0.0508 (4)
H37	0.1233	0.1337	−0.3068	0.061*
C38	0.26201 (19)	0.28700 (18)	−0.25794 (15)	0.0533 (5)
H38	0.2359	0.3039	−0.3270	0.064*
C39	0.3665 (2)	0.36332 (17)	−0.16918 (18)	0.0548 (5)
H39	0.4127	0.4328	−0.1772	0.066*
C40	0.40430 (17)	0.33878 (14)	−0.06819 (15)	0.0421 (4)
H40	0.4760	0.3920	−0.0072	0.051*

	U11	U22	U33	U12	U13	U23
Cl1	0.0299 (2)	0.0611 (3)	0.0746 (3)	0.01170 (18)	0.0276 (2)	0.0141 (2)
Cl2	0.0353 (2)	0.0478 (2)	0.0438 (2)	−0.01135 (17)	0.00949 (17)	0.00916 (17)
O1	0.0228 (5)	0.0269 (5)	0.0287 (5)	0.0040 (4)	0.0044 (4)	0.0078 (4)
O2	0.0223 (5)	0.0362 (5)	0.0248 (5)	0.0045 (4)	0.0066 (4)	0.0106 (4)
O3	0.0484 (7)	0.0467 (6)	0.0331 (5)	0.0200 (5)	0.0126 (5)	0.0194 (5)
O4	0.0443 (6)	0.0435 (6)	0.0565 (7)	0.0224 (5)	0.0227 (5)	0.0232 (5)
C1	0.0249 (7)	0.0301 (6)	0.0269 (7)	0.0019 (5)	0.0100 (5)	0.0072 (5)
C2	0.0330 (7)	0.0331 (7)	0.0287 (7)	0.0028 (6)	0.0095 (6)	0.0100 (6)
C3	0.0453 (9)	0.0429 (8)	0.0285 (7)	0.0043 (7)	0.0130 (6)	0.0140 (6)
C4	0.0463 (9)	0.0443 (8)	0.0305 (7)	0.0018 (7)	0.0203 (7)	0.0080 (6)
C5	0.0343 (8)	0.0344 (7)	0.0330 (7)	0.0001 (6)	0.0172 (6)	0.0042 (6)
C6	0.0388 (8)	0.0399 (8)	0.0418 (8)	0.0051 (7)	0.0234 (7)	0.0021 (7)
C7	0.0337 (8)	0.0353 (7)	0.0509 (9)	0.0093 (6)	0.0205 (7)	0.0031 (7)
C8	0.0285 (7)	0.0303 (7)	0.0397 (8)	0.0047 (6)	0.0127 (6)	0.0072 (6)
C9	0.0233 (6)	0.0287 (6)	0.0296 (7)	0.0028 (5)	0.0099 (5)	0.0052 (5)
C10	0.0252 (7)	0.0285 (6)	0.0289 (7)	0.0000 (5)	0.0103 (5)	0.0045 (5)
C11	0.0230 (6)	0.0280 (6)	0.0234 (6)	0.0041 (5)	0.0068 (5)	0.0077 (5)
C12	0.0279 (7)	0.0360 (7)	0.0269 (7)	0.0068 (6)	0.0054 (6)	0.0078 (6)
C13	0.0242 (7)	0.0271 (6)	0.0264 (6)	0.0055 (5)	0.0075 (5)	0.0094 (5)
C14	0.0232 (7)	0.0399 (8)	0.0394 (8)	0.0052 (6)	0.0031 (6)	0.0094 (6)
C15	0.0254 (7)	0.0350 (7)	0.0475 (8)	0.0089 (6)	0.0166 (6)	0.0139 (6)
C16	0.0321 (7)	0.0364 (7)	0.0329 (7)	0.0090 (6)	0.0152 (6)	0.0106 (6)
C17	0.0257 (7)	0.0346 (7)	0.0262 (6)	0.0061 (5)	0.0069 (5)	0.0095 (5)
C18	0.0237 (6)	0.0293 (6)	0.0255 (6)	0.0062 (5)	0.0083 (5)	0.0087 (5)
C19	0.0247 (7)	0.0280 (6)	0.0286 (6)	0.0065 (5)	0.0085 (5)	0.0104 (5)
C20	0.0297 (7)	0.0309 (7)	0.0284 (7)	0.0071 (6)	0.0114 (6)	0.0090 (5)
C21	0.0326 (7)	0.0310 (7)	0.0295 (7)	0.0046 (6)	0.0068 (6)	0.0067 (6)
C22	0.0273 (7)	0.0315 (7)	0.0361 (7)	0.0006 (6)	0.0068 (6)	0.0109 (6)
C23	0.0326 (8)	0.0403 (8)	0.0335 (7)	0.0031 (6)	0.0140 (6)	0.0135 (6)
C24	0.0305 (7)	0.0349 (7)	0.0273 (7)	0.0039 (6)	0.0093 (6)	0.0092 (6)
C25	0.0537 (10)	0.0538 (10)	0.0401 (9)	0.0176 (8)	0.0058 (8)	0.0224 (8)
C26	0.0599 (12)	0.0563 (11)	0.0831 (14)	0.0353 (10)	0.0266 (11)	0.0307 (10)
C27	0.0268 (7)	0.0288 (7)	0.0348 (7)	0.0087 (5)	0.0066 (6)	0.0079 (6)
C28	0.0288 (7)	0.0323 (7)	0.0225 (6)	0.0071 (6)	0.0063 (5)	0.0115 (5)
C29	0.0328 (8)	0.0370 (7)	0.0301 (7)	0.0097 (6)	0.0115 (6)	0.0107 (6)
C30	0.0335 (8)	0.0534 (9)	0.0399 (8)	0.0117 (7)	0.0176 (7)	0.0189 (7)
C31	0.0348 (8)	0.0531 (10)	0.0529 (10)	−0.0003 (7)	0.0148 (7)	0.0258 (8)
C32	0.0456 (10)	0.0338 (8)	0.0556 (10)	−0.0004 (7)	0.0111 (8)	0.0171 (7)
C33	0.0385 (8)	0.0324 (7)	0.0375 (8)	0.0090 (6)	0.0094 (6)	0.0122 (6)
C34	0.0227 (7)	0.0374 (7)	0.0328 (7)	0.0023 (6)	0.0065 (6)	0.0130 (6)
C35	0.0245 (7)	0.0326 (7)	0.0339 (7)	0.0117 (5)	0.0110 (6)	0.0123 (6)
C36	0.0315 (8)	0.0426 (8)	0.0396 (8)	0.0075 (6)	0.0057 (6)	0.0159 (7)
C37	0.0410 (9)	0.0684 (11)	0.0380 (9)	0.0157 (8)	0.0026 (7)	0.0182 (8)
C38	0.0527 (11)	0.0813 (13)	0.0447 (9)	0.0325 (10)	0.0188 (8)	0.0392 (9)
C39	0.0545 (11)	0.0576 (11)	0.0680 (12)	0.0182 (9)	0.0243 (9)	0.0425 (10)
C40	0.0414 (9)	0.0371 (8)	0.0464 (9)	0.0072 (7)	0.0110 (7)	0.0183 (7)

Cl1—C15	1.7414 (15)	C20—C21	1.389 (2)
Cl2—C22	1.7435 (14)	C20—H20	0.9500
O1—C27	1.4320 (16)	C21—C22	1.382 (2)
O1—C11	1.4359 (15)	C21—H21	0.9500
O2—C18	1.4167 (15)	C22—C23	1.382 (2)
O2—C34	1.4295 (16)	C23—C24	1.384 (2)
O3—C2	1.3680 (19)	C23—H23	0.9500
O3—C25	1.4235 (18)	C24—H24	0.9500
O4—C8	1.3621 (19)	C25—H25A	0.9800
O4—C26	1.428 (2)	C25—H25B	0.9800
C1—C2	1.376 (2)	C25—H25C	0.9800
C1—C10	1.410 (2)	C26—H26A	0.9800
C1—C11	1.5267 (18)	C26—H26B	0.9800
C2—C3	1.424 (2)	C26—H26C	0.9800
C3—C4	1.371 (2)	C27—C28	1.5044 (19)
C3—H3	0.9500	C27—H27A	0.9900
C4—C5	1.416 (2)	C27—H27B	0.9900
C4—H4	0.9500	C28—C29	1.391 (2)
C5—C10	1.412 (2)	C28—C33	1.392 (2)
C5—C6	1.416 (2)	C29—C30	1.388 (2)
C6—C7	1.366 (2)	C29—H29	0.9500
C6—H6	0.9500	C30—C31	1.384 (2)
C7—C8	1.422 (2)	C30—H30	0.9500
C7—H7	0.9500	C31—C32	1.380 (3)
C8—C9	1.379 (2)	C31—H31	0.9500
C9—C10	1.4006 (19)	C32—C33	1.387 (2)
C9—C18	1.5230 (19)	C32—H32	0.9500
C11—C13	1.5089 (18)	C33—H33	0.9500
C11—C18	1.6277 (18)	C34—C35	1.5050 (19)
C12—C14	1.385 (2)	C34—H34A	0.9900
C12—C13	1.3949 (18)	C34—H34B	0.9900
C12—H12	0.9500	C35—C36	1.386 (2)
C13—C17	1.3913 (19)	C35—C40	1.387 (2)
C14—C15	1.384 (2)	C36—C37	1.385 (2)
C14—H14	0.9500	C36—H36	0.9500
C15—C16	1.380 (2)	C37—C38	1.376 (3)
C16—C17	1.383 (2)	C37—H37	0.9500
C16—H16	0.9500	C38—C39	1.379 (3)
C17—H17	0.9500	C38—H38	0.9500
C18—C19	1.5355 (18)	C39—C40	1.387 (2)
C19—C24	1.394 (2)	C39—H39	0.9500
C19—C20	1.3947 (19)	C40—H40	0.9500
C27—O1—C11	115.90 (10)	C22—C21—H21	120.4
C18—O2—C34	119.75 (10)	C20—C21—H21	120.4
C2—O3—C25	118.69 (13)	C23—C22—C21	120.94 (13)
C8—O4—C26	118.61 (14)	C23—C22—Cl2	119.27 (12)
C2—C1—C10	118.46 (13)	C21—C22—Cl2	119.79 (11)
C2—C1—C11	133.47 (13)	C22—C23—C24	119.35 (14)
C10—C1—C11	107.80 (11)	C22—C23—H23	120.3
O3—C2—C1	118.01 (13)	C24—C23—H23	120.3
O3—C2—C3	122.65 (13)	C23—C24—C19	121.21 (13)
C1—C2—C3	119.32 (14)	C23—C24—H24	119.4
C4—C3—C2	121.51 (14)	C19—C24—H24	119.4
C4—C3—H3	119.2	O3—C25—H25A	109.5
C2—C3—H3	119.2	O3—C25—H25B	109.5
C3—C4—C5	121.07 (14)	H25A—C25—H25B	109.5
C3—C4—H4	119.5	O3—C25—H25C	109.5
C5—C4—H4	119.5	H25A—C25—H25C	109.5
C10—C5—C4	116.08 (14)	H25B—C25—H25C	109.5
C10—C5—C6	116.03 (14)	O4—C26—H26A	109.5
C4—C5—C6	127.84 (14)	O4—C26—H26B	109.5
C7—C6—C5	121.22 (14)	H26A—C26—H26B	109.5
C7—C6—H6	119.4	O4—C26—H26C	109.5
C5—C6—H6	119.4	H26A—C26—H26C	109.5
C6—C7—C8	121.50 (14)	H26B—C26—H26C	109.5
C6—C7—H7	119.3	O1—C27—C28	109.42 (11)
C8—C7—H7	119.3	O1—C27—H27A	109.8
O4—C8—C9	117.19 (13)	C28—C27—H27A	109.8
O4—C8—C7	123.92 (14)	O1—C27—H27B	109.8
C9—C8—C7	118.88 (14)	C28—C27—H27B	109.8
C8—C9—C10	118.99 (13)	H27A—C27—H27B	108.2
C8—C9—C18	131.49 (13)	C29—C28—C33	118.75 (14)
C10—C9—C18	108.56 (12)	C29—C28—C27	121.35 (12)
C9—C10—C1	113.21 (12)	C33—C28—C27	119.90 (13)
C9—C10—C5	123.21 (14)	C30—C29—C28	120.52 (14)
C1—C10—C5	123.50 (13)	C30—C29—H29	119.7
O1—C11—C13	111.10 (10)	C28—C29—H29	119.7
O1—C11—C1	108.72 (10)	C31—C30—C29	120.34 (16)
C13—C11—C1	119.20 (11)	C31—C30—H30	119.8
O1—C11—C18	103.24 (9)	C29—C30—H30	119.8
C13—C11—C18	111.09 (10)	C32—C31—C30	119.38 (15)
C1—C11—C18	102.01 (10)	C32—C31—H31	120.3
C14—C12—C13	120.71 (13)	C30—C31—H31	120.3
C14—C12—H12	119.6	C31—C32—C33	120.65 (15)
C13—C12—H12	119.6	C31—C32—H32	119.7
C17—C13—C12	118.78 (13)	C33—C32—H32	119.7
C17—C13—C11	118.42 (11)	C32—C33—C28	120.34 (15)
C12—C13—C11	122.46 (12)	C32—C33—H33	119.8
C15—C14—C12	118.91 (13)	C28—C33—H33	119.8
C15—C14—H14	120.5	O2—C34—C35	108.48 (11)
C12—C14—H14	120.5	O2—C34—H34A	110.0
C16—C15—C14	121.71 (13)	C35—C34—H34A	110.0
C16—C15—Cl1	118.59 (12)	O2—C34—H34B	110.0
C14—C15—Cl1	119.70 (12)	C35—C34—H34B	110.0
C15—C16—C17	118.71 (13)	H34A—C34—H34B	108.4
C15—C16—H16	120.6	C36—C35—C40	118.50 (14)
C17—C16—H16	120.6	C36—C35—C34	119.35 (13)
C16—C17—C13	121.17 (13)	C40—C35—C34	122.14 (13)
C16—C17—H17	119.4	C37—C36—C35	120.80 (15)
C13—C17—H17	119.4	C37—C36—H36	119.6
O2—C18—C9	118.69 (11)	C35—C36—H36	119.6
O2—C18—C19	104.84 (10)	C38—C37—C36	120.20 (17)
C9—C18—C19	110.59 (11)	C38—C37—H37	119.9
O2—C18—C11	111.71 (10)	C36—C37—H37	119.9
C9—C18—C11	101.83 (10)	C37—C38—C39	119.70 (15)
C19—C18—C11	109.05 (10)	C37—C38—H38	120.2
C24—C19—C20	118.16 (13)	C39—C38—H38	120.2
C24—C19—C18	120.05 (12)	C38—C39—C40	120.14 (16)
C20—C19—C18	121.67 (12)	C38—C39—H39	119.9
C21—C20—C19	121.12 (13)	C40—C39—H39	119.9
C21—C20—H20	119.4	C35—C40—C39	120.66 (16)
C19—C20—H20	119.4	C35—C40—H40	119.7
C22—C21—C20	119.19 (13)	C39—C40—H40	119.7
C25—O3—C2—C1	164.83 (14)	C11—C13—C17—C16	172.21 (12)
C25—O3—C2—C3	−16.4 (2)	C34—O2—C18—C9	−31.50 (16)
C10—C1—C2—O3	178.58 (12)	C34—O2—C18—C19	−155.53 (11)
C11—C1—C2—O3	5.4 (2)	C34—O2—C18—C11	86.51 (14)
C10—C1—C2—C3	−0.2 (2)	C8—C9—C18—O2	−48.2 (2)
C11—C1—C2—C3	−173.39 (14)	C10—C9—C18—O2	143.42 (12)
O3—C2—C3—C4	−176.86 (14)	C8—C9—C18—C19	72.93 (18)
C1—C2—C3—C4	1.9 (2)	C10—C9—C18—C19	−95.42 (12)
C2—C3—C4—C5	−1.6 (2)	C8—C9—C18—C11	−171.29 (14)
C3—C4—C5—C10	−0.4 (2)	C10—C9—C18—C11	20.36 (13)
C3—C4—C5—C6	−178.05 (15)	O1—C11—C18—O2	−39.72 (13)
C10—C5—C6—C7	−2.3 (2)	C13—C11—C18—O2	79.42 (13)
C4—C5—C6—C7	175.37 (15)	C1—C11—C18—O2	−152.50 (10)
C5—C6—C7—C8	−1.3 (2)	O1—C11—C18—C9	87.97 (11)
C26—O4—C8—C9	167.89 (15)	C13—C11—C18—C9	−152.88 (10)
C26—O4—C8—C7	−13.6 (2)	C1—C11—C18—C9	−24.81 (12)
C6—C7—C8—O4	−174.33 (14)	O1—C11—C18—C19	−155.13 (10)
C6—C7—C8—C9	4.1 (2)	C13—C11—C18—C19	−35.98 (14)
O4—C8—C9—C10	175.50 (12)	C1—C11—C18—C19	92.09 (12)
C7—C8—C9—C10	−3.1 (2)	O2—C18—C19—C24	−27.44 (16)
O4—C8—C9—C18	8.1 (2)	C9—C18—C19—C24	−156.49 (12)
C7—C8—C9—C18	−170.44 (14)	C11—C18—C19—C24	92.32 (14)
C8—C9—C10—C1	−177.65 (12)	O2—C18—C19—C20	156.65 (12)
C18—C9—C10—C1	−7.61 (15)	C9—C18—C19—C20	27.60 (17)
C8—C9—C10—C5	−0.7 (2)	C11—C18—C19—C20	−83.59 (15)
C18—C9—C10—C5	169.36 (12)	C24—C19—C20—C21	−1.5 (2)
C2—C1—C10—C9	175.18 (12)	C18—C19—C20—C21	174.45 (12)
C11—C1—C10—C9	−10.03 (15)	C19—C20—C21—C22	0.0 (2)
C2—C1—C10—C5	−1.8 (2)	C20—C21—C22—C23	1.3 (2)
C11—C1—C10—C5	173.01 (12)	C20—C21—C22—Cl2	−178.48 (11)
C4—C5—C10—C9	−174.59 (13)	C21—C22—C23—C24	−1.0 (2)
C6—C5—C10—C9	3.4 (2)	Cl2—C22—C23—C24	178.78 (12)
C4—C5—C10—C1	2.1 (2)	C22—C23—C24—C19	−0.6 (2)
C6—C5—C10—C1	−179.96 (13)	C20—C19—C24—C23	1.8 (2)
C27—O1—C11—C13	65.90 (14)	C18—C19—C24—C23	−174.20 (13)
C27—O1—C11—C1	−67.17 (14)	C11—O1—C27—C28	138.79 (11)
C27—O1—C11—C18	−174.96 (10)	O1—C27—C28—C29	−29.00 (17)
C2—C1—C11—O1	86.75 (17)	O1—C27—C28—C33	151.23 (12)
C10—C1—C11—O1	−86.93 (12)	C33—C28—C29—C30	−0.7 (2)
C2—C1—C11—C13	−41.9 (2)	C27—C28—C29—C30	179.54 (13)
C10—C1—C11—C13	144.40 (12)	C28—C29—C30—C31	0.4 (2)
C2—C1—C11—C18	−164.62 (15)	C29—C30—C31—C32	0.4 (2)
C10—C1—C11—C18	21.69 (13)	C30—C31—C32—C33	−0.9 (3)
C14—C12—C13—C17	0.7 (2)	C31—C32—C33—C28	0.6 (2)
C14—C12—C13—C11	−172.46 (13)	C29—C28—C33—C32	0.2 (2)
O1—C11—C13—C17	35.72 (15)	C27—C28—C33—C32	179.96 (14)
C1—C11—C13—C17	163.29 (12)	C18—O2—C34—C35	159.31 (11)
C18—C11—C13—C17	−78.61 (14)	O2—C34—C35—C36	148.56 (13)
O1—C11—C13—C12	−151.08 (12)	O2—C34—C35—C40	−31.88 (19)
C1—C11—C13—C12	−23.51 (18)	C40—C35—C36—C37	−0.4 (2)
C18—C11—C13—C12	94.59 (14)	C34—C35—C36—C37	179.15 (15)
C13—C12—C14—C15	0.4 (2)	C35—C36—C37—C38	0.7 (3)
C12—C14—C15—C16	−1.0 (2)	C36—C37—C38—C39	−0.4 (3)
C12—C14—C15—Cl1	178.80 (11)	C37—C38—C39—C40	−0.2 (3)
C14—C15—C16—C17	0.5 (2)	C36—C35—C40—C39	−0.1 (2)
Cl1—C15—C16—C17	−179.31 (11)	C34—C35—C40—C39	−179.71 (16)
C15—C16—C17—C13	0.7 (2)	C38—C39—C40—C35	0.5 (3)
C12—C13—C17—C16	−1.2 (2)

Cg6 is the centroid of the C35–C40 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C34—H34A···Cl1i	0.99	2.66	3.4748 (16)	140
C16—H16···Cg6ii	0.95	2.70	3.3962 (16)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg6 is the centroid of the C35–C40 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C34—H34A⋯Cl1i	0.99	2.66	3.4748 (16)	140
C16—H16⋯Cg6ii	0.95	2.70	3.3962 (16)	131

Symmetry codes: (i) ; (ii) .