(4-Fluoro-phen-yl)[8-(4-fluoro-benzo-yl)-2,7-diphen-oxy-naphthalen-1-yl]methan-one.

In the title compound, C(36)H(22)F(2)O(4), the aromatic rings of the benzoyl and phen-oxy groups make dihedral angles of 72.07 (5), 73.24 (5), 62.49 (5) and 77.96 (6)° with the naphthalene ring system. In the crystal, C-H⋯O hydrogen bonds and C-H⋯π inter-actions are observed.

Related literature

For information on electrophilic aromatic aroylation of the naphthalene core, see: Okamoto & Yonezawa (2009 ▶); Okamoto et al. (2011 ▶, 2012 ▶). For the structures of closely related compounds, see: Watanabe et al. (2010 ▶); Sakamoto et al. (2012 ▶).

Experimental

Crystal data

C36H22F2O4

M = 556.54

Orthorhombic,

a = 22.3058 (4) Å

b = 14.6047 (3) Å

c = 16.8302 (3) Å

V = 5482.76 (18) Å3

Z = 8

Cu Kα radiation

μ = 0.80 mm−1

T = 193 K

0.50 × 0.30 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: numerical (NUMABS; Higashi, 1999 ▶) T min = 0.691, T max = 0.925

96215 measured reflections

5011 independent reflections

4671 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.091

S = 1.06

5011 reflections

380 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.16 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/S160053681204408X/rz5018sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681204408X/rz5018Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S160053681204408X/rz5018Isup3.cml

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

C36H22F2O4	F(000) = 2304
Mr = 556.54	Dx = 1.348 Mg m−3
Orthorhombic, Pbcn	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -P 2n 2ab	Cell parameters from 89526 reflections
a = 22.3058 (4) Å	θ = 3.0–68.2°
b = 14.6047 (3) Å	µ = 0.80 mm−1
c = 16.8302 (3) Å	T = 193 K
V = 5482.76 (18) Å3	Block, colorless
Z = 8	0.50 × 0.30 × 0.10 mm

Rigaku R-AXIS RAPID diffractometer	5011 independent reflections
Radiation source: rotating anode	4671 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 10.000 pixels mm-1	θmax = 68.2°, θmin = 3.6°
ω scans	h = −26→26
Absorption correction: numerical (NUMABS; Higashi, 1999)	k = −17→17
Tmin = 0.691, Tmax = 0.925	l = −19→19
96215 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)] = 0.035	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0435P)2 + 1.3362P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max < 0.001
5011 reflections	Δρmax = 0.17 e Å−3
380 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: 0.00098 (6)

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
F1	0.42732 (5)	0.97093 (6)	0.71349 (6)	0.0794 (3)
F2	0.21941 (5)	0.25563 (7)	0.76820 (6)	0.0814 (3)
O1	0.51813 (4)	0.65226 (6)	0.53754 (5)	0.0445 (2)
O2	0.22348 (4)	0.46286 (6)	0.46362 (5)	0.0476 (2)
O3	0.40405 (4)	0.54759 (6)	0.64967 (5)	0.0436 (2)
O4	0.28295 (4)	0.62180 (6)	0.58844 (6)	0.0485 (2)
C1	0.42155 (5)	0.59134 (7)	0.51684 (7)	0.0354 (3)
C2	0.47700 (5)	0.61326 (8)	0.48603 (7)	0.0392 (3)
C3	0.49455 (6)	0.58889 (8)	0.40848 (8)	0.0452 (3)
H3	0.5336	0.6032	0.3895	0.054*
C4	0.45474 (6)	0.54468 (8)	0.36146 (8)	0.0450 (3)
H4	0.4662	0.5284	0.3090	0.054*
C5	0.39650 (6)	0.52212 (7)	0.38826 (7)	0.0393 (3)
C6	0.35582 (6)	0.47834 (8)	0.33668 (7)	0.0437 (3)
H6	0.3679	0.4649	0.2838	0.052*
C7	0.29964 (6)	0.45476 (8)	0.36058 (7)	0.0430 (3)
H7	0.2729	0.4244	0.3254	0.052*
C8	0.28201 (5)	0.47632 (8)	0.43851 (7)	0.0389 (3)
C9	0.31971 (5)	0.51855 (7)	0.49203 (7)	0.0353 (3)
C10	0.37908 (5)	0.54365 (7)	0.46804 (7)	0.0351 (3)
C11	0.41193 (5)	0.61111 (8)	0.60379 (7)	0.0362 (3)
C12	0.41448 (5)	0.70744 (8)	0.63178 (7)	0.0380 (3)
C13	0.40891 (6)	0.78060 (9)	0.57966 (8)	0.0460 (3)
H13	0.4022	0.7693	0.5248	0.055*
C14	0.41308 (7)	0.87001 (9)	0.60688 (9)	0.0549 (3)
H14	0.4093	0.9203	0.5714	0.066*
C15	0.42273 (7)	0.88356 (9)	0.68609 (9)	0.0542 (3)
C16	0.42761 (7)	0.81373 (10)	0.73981 (8)	0.0536 (3)
H16	0.4338	0.8260	0.7946	0.064*
C17	0.42336 (6)	0.72486 (9)	0.71226 (8)	0.0458 (3)
H17	0.4265	0.6752	0.7485	0.055*
C18	0.29239 (5)	0.54231 (8)	0.57138 (7)	0.0364 (3)
C19	0.27487 (5)	0.46544 (8)	0.62434 (7)	0.0380 (3)
C20	0.23468 (6)	0.48195 (10)	0.68603 (7)	0.0466 (3)
H20	0.2197	0.5420	0.6946	0.056*
C21	0.21664 (6)	0.41109 (11)	0.73482 (8)	0.0576 (4)
H21	0.1895	0.4219	0.7773	0.069*
C22	0.23845 (7)	0.32519 (11)	0.72109 (8)	0.0564 (4)
C23	0.27865 (7)	0.30606 (10)	0.66188 (9)	0.0555 (4)
H23	0.2936	0.2457	0.6544	0.067*
C24	0.29691 (6)	0.37735 (9)	0.61327 (8)	0.0469 (3)
H24	0.3248	0.3659	0.5718	0.056*
C25	0.55286 (5)	0.72530 (8)	0.51134 (8)	0.0413 (3)
C26	0.53493 (6)	0.78388 (9)	0.45175 (9)	0.0541 (3)
H26	0.4978	0.7747	0.4254	0.065*
C27	0.57176 (7)	0.85648 (10)	0.43073 (10)	0.0621 (4)
H27	0.5600	0.8965	0.3890	0.075*
C28	0.62528 (7)	0.87125 (10)	0.46961 (10)	0.0591 (4)
H28	0.6504	0.9209	0.4548	0.071*
C29	0.64195 (6)	0.81319 (10)	0.53019 (10)	0.0562 (4)
H29	0.6784	0.8238	0.5578	0.067*
C30	0.60613 (6)	0.73941 (9)	0.55138 (8)	0.0473 (3)
H30	0.6181	0.6992	0.5928	0.057*
C31	0.18912 (6)	0.39816 (9)	0.42294 (7)	0.0441 (3)
C32	0.20515 (7)	0.30699 (10)	0.42398 (9)	0.0570 (4)
H32	0.2393	0.2873	0.4530	0.068*
C33	0.17099 (8)	0.24501 (11)	0.38237 (11)	0.0675 (4)
H33	0.1820	0.1822	0.3819	0.081*
C34	0.12115 (9)	0.27327 (12)	0.34162 (10)	0.0717 (5)
H34	0.0982	0.2302	0.3123	0.086*
C35	0.10419 (8)	0.36443 (12)	0.34296 (10)	0.0678 (4)
H35	0.0690	0.3835	0.3158	0.081*
C36	0.13857 (6)	0.42802 (10)	0.38408 (8)	0.0524 (3)
H36	0.1274	0.4908	0.3853	0.063*

	U11	U22	U33	U12	U13	U23
F1	0.1211 (8)	0.0418 (5)	0.0751 (6)	−0.0105 (5)	0.0047 (6)	−0.0162 (4)
F2	0.0877 (7)	0.0902 (7)	0.0662 (6)	−0.0393 (6)	−0.0098 (5)	0.0362 (5)
O1	0.0405 (4)	0.0453 (5)	0.0476 (5)	−0.0009 (4)	0.0052 (4)	0.0125 (4)
O2	0.0421 (5)	0.0541 (5)	0.0467 (5)	0.0010 (4)	0.0022 (4)	−0.0123 (4)
O3	0.0529 (5)	0.0386 (4)	0.0393 (4)	0.0002 (4)	0.0101 (4)	0.0055 (4)
O4	0.0537 (5)	0.0363 (5)	0.0555 (6)	0.0036 (4)	0.0137 (4)	−0.0079 (4)
C1	0.0413 (6)	0.0277 (5)	0.0371 (6)	0.0062 (4)	0.0077 (5)	0.0052 (4)
C2	0.0423 (6)	0.0309 (5)	0.0444 (7)	0.0045 (5)	0.0068 (5)	0.0083 (5)
C3	0.0478 (7)	0.0369 (6)	0.0510 (7)	0.0052 (5)	0.0200 (6)	0.0087 (5)
C4	0.0601 (8)	0.0349 (6)	0.0399 (6)	0.0075 (5)	0.0196 (6)	0.0039 (5)
C5	0.0534 (7)	0.0285 (5)	0.0360 (6)	0.0081 (5)	0.0114 (5)	0.0038 (4)
C6	0.0649 (8)	0.0339 (6)	0.0322 (6)	0.0077 (5)	0.0092 (5)	0.0010 (5)
C7	0.0567 (7)	0.0358 (6)	0.0363 (6)	0.0049 (5)	0.0000 (5)	−0.0010 (5)
C8	0.0446 (6)	0.0335 (6)	0.0387 (6)	0.0052 (5)	0.0038 (5)	0.0010 (5)
C9	0.0428 (6)	0.0292 (5)	0.0339 (6)	0.0055 (4)	0.0059 (5)	0.0014 (4)
C10	0.0447 (6)	0.0257 (5)	0.0350 (6)	0.0063 (4)	0.0080 (5)	0.0042 (4)
C11	0.0336 (5)	0.0358 (6)	0.0391 (6)	0.0021 (4)	0.0044 (5)	0.0036 (5)
C12	0.0359 (6)	0.0379 (6)	0.0402 (6)	0.0000 (5)	0.0042 (5)	−0.0003 (5)
C13	0.0555 (7)	0.0394 (6)	0.0432 (7)	0.0061 (5)	−0.0017 (6)	−0.0006 (5)
C14	0.0733 (9)	0.0370 (7)	0.0545 (8)	0.0054 (6)	−0.0004 (7)	0.0020 (6)
C15	0.0654 (9)	0.0373 (7)	0.0598 (9)	−0.0044 (6)	0.0045 (7)	−0.0093 (6)
C16	0.0637 (9)	0.0530 (8)	0.0442 (7)	−0.0099 (7)	0.0016 (6)	−0.0088 (6)
C17	0.0513 (7)	0.0443 (7)	0.0418 (7)	−0.0059 (6)	0.0023 (5)	0.0020 (5)
C18	0.0348 (6)	0.0359 (6)	0.0386 (6)	0.0016 (4)	0.0039 (5)	−0.0057 (5)
C19	0.0393 (6)	0.0412 (6)	0.0334 (6)	−0.0057 (5)	0.0017 (5)	−0.0046 (5)
C20	0.0448 (7)	0.0563 (8)	0.0388 (6)	−0.0088 (6)	0.0051 (5)	−0.0083 (6)
C21	0.0541 (8)	0.0796 (11)	0.0391 (7)	−0.0206 (7)	0.0078 (6)	0.0003 (7)
C22	0.0619 (8)	0.0653 (9)	0.0419 (7)	−0.0281 (7)	−0.0080 (6)	0.0135 (6)
C23	0.0700 (9)	0.0433 (7)	0.0532 (8)	−0.0095 (6)	−0.0081 (7)	0.0063 (6)
C24	0.0571 (8)	0.0416 (7)	0.0420 (7)	−0.0025 (6)	0.0040 (6)	−0.0008 (5)
C25	0.0392 (6)	0.0385 (6)	0.0462 (7)	0.0029 (5)	0.0081 (5)	0.0035 (5)
C26	0.0507 (7)	0.0469 (7)	0.0646 (9)	−0.0070 (6)	−0.0085 (6)	0.0148 (6)
C27	0.0709 (10)	0.0485 (8)	0.0670 (10)	−0.0130 (7)	−0.0058 (8)	0.0161 (7)
C28	0.0567 (8)	0.0461 (8)	0.0746 (10)	−0.0121 (6)	0.0074 (7)	0.0004 (7)
C29	0.0444 (7)	0.0508 (8)	0.0735 (9)	−0.0006 (6)	−0.0038 (7)	−0.0107 (7)
C30	0.0461 (7)	0.0451 (7)	0.0506 (7)	0.0074 (6)	−0.0005 (6)	−0.0016 (6)
C31	0.0488 (7)	0.0432 (6)	0.0402 (6)	−0.0043 (5)	0.0044 (5)	−0.0006 (5)
C32	0.0629 (9)	0.0462 (8)	0.0618 (9)	0.0035 (6)	0.0119 (7)	0.0038 (7)
C33	0.0829 (11)	0.0433 (8)	0.0762 (11)	−0.0127 (8)	0.0268 (9)	−0.0024 (7)
C34	0.0889 (12)	0.0621 (10)	0.0641 (10)	−0.0392 (9)	0.0133 (9)	−0.0073 (8)
C35	0.0662 (10)	0.0737 (11)	0.0635 (10)	−0.0264 (8)	−0.0110 (8)	0.0130 (8)
C36	0.0544 (8)	0.0462 (7)	0.0566 (8)	−0.0089 (6)	−0.0034 (6)	0.0088 (6)

F1—C15	1.3607 (15)	C17—H17	0.9500
F2—C22	1.3569 (15)	C18—C19	1.4858 (17)
O1—C2	1.3848 (15)	C19—C24	1.3899 (17)
O1—C25	1.3902 (14)	C19—C20	1.3928 (17)
O2—C8	1.3863 (14)	C20—C21	1.3810 (19)
O2—C31	1.3959 (15)	C20—H20	0.9500
O3—C11	1.2198 (14)	C21—C22	1.365 (2)
O4—C18	1.2144 (14)	C21—H21	0.9500
C1—C2	1.3788 (16)	C22—C23	1.369 (2)
C1—C10	1.4343 (17)	C23—C24	1.3854 (19)
C1—C11	1.5069 (16)	C23—H23	0.9500
C2—C3	1.4084 (17)	C24—H24	0.9500
C3—C4	1.3534 (19)	C25—C26	1.3776 (18)
C3—H3	0.9500	C25—C30	1.3815 (18)
C4—C5	1.4141 (17)	C26—C27	1.3872 (19)
C4—H4	0.9500	C26—H26	0.9500
C5—C6	1.4092 (18)	C27—C28	1.378 (2)
C5—C10	1.4326 (16)	C27—H27	0.9500
C6—C7	1.3605 (19)	C28—C29	1.377 (2)
C6—H6	0.9500	C28—H28	0.9500
C7—C8	1.4049 (17)	C29—C30	1.388 (2)
C7—H7	0.9500	C29—H29	0.9500
C8—C9	1.3781 (17)	C30—H30	0.9500
C9—C10	1.4322 (16)	C31—C36	1.3746 (19)
C9—C18	1.5084 (15)	C31—C32	1.3788 (19)
C11—C12	1.4846 (16)	C32—C33	1.375 (2)
C12—C13	1.3881 (17)	C32—H32	0.9500
C12—C17	1.3924 (18)	C33—C34	1.370 (3)
C13—C14	1.3869 (18)	C33—H33	0.9500
C13—H13	0.9500	C34—C35	1.384 (3)
C14—C15	1.365 (2)	C34—H34	0.9500
C14—H14	0.9500	C35—C36	1.389 (2)
C15—C16	1.367 (2)	C35—H35	0.9500
C16—C17	1.3815 (19)	C36—H36	0.9500
C16—H16	0.9500
C2—O1—C25	119.09 (9)	C19—C18—C9	117.62 (9)
C8—O2—C31	117.61 (9)	C24—C19—C20	119.20 (12)
C2—C1—C10	119.33 (10)	C24—C19—C18	121.73 (11)
C2—C1—C11	116.65 (11)	C20—C19—C18	119.06 (11)
C10—C1—C11	123.72 (10)	C21—C20—C19	120.07 (13)
C1—C2—O1	117.02 (10)	C21—C20—H20	120.0
C1—C2—C3	122.63 (12)	C19—C20—H20	120.0
O1—C2—C3	120.00 (11)	C22—C21—C20	118.95 (13)
C4—C3—C2	118.69 (11)	C22—C21—H21	120.5
C4—C3—H3	120.7	C20—C21—H21	120.5
C2—C3—H3	120.7	F2—C22—C21	118.52 (14)
C3—C4—C5	121.83 (11)	F2—C22—C23	118.52 (15)
C3—C4—H4	119.1	C21—C22—C23	122.96 (13)
C5—C4—H4	119.1	C22—C23—C24	117.97 (14)
C6—C5—C4	120.04 (11)	C22—C23—H23	121.0
C6—C5—C10	120.15 (11)	C24—C23—H23	121.0
C4—C5—C10	119.80 (12)	C23—C24—C19	120.82 (13)
C7—C6—C5	121.72 (11)	C23—C24—H24	119.6
C7—C6—H6	119.1	C19—C24—H24	119.6
C5—C6—H6	119.1	C26—C25—C30	120.81 (12)
C6—C7—C8	118.50 (12)	C26—C25—O1	123.07 (11)
C6—C7—H7	120.8	C30—C25—O1	116.04 (11)
C8—C7—H7	120.8	C25—C26—C27	119.24 (13)
C9—C8—O2	116.03 (10)	C25—C26—H26	120.4
C9—C8—C7	122.67 (11)	C27—C26—H26	120.4
O2—C8—C7	121.09 (11)	C28—C27—C26	120.76 (14)
C8—C9—C10	119.64 (10)	C28—C27—H27	119.6
C8—C9—C18	115.79 (10)	C26—C27—H27	119.6
C10—C9—C18	124.36 (10)	C29—C28—C27	119.27 (13)
C9—C10—C5	117.31 (11)	C29—C28—H28	120.4
C9—C10—C1	124.99 (10)	C27—C28—H28	120.4
C5—C10—C1	117.66 (10)	C28—C29—C30	120.85 (13)
O3—C11—C12	121.69 (11)	C28—C29—H29	119.6
O3—C11—C1	119.31 (10)	C30—C29—H29	119.6
C12—C11—C1	118.97 (10)	C25—C30—C29	119.05 (13)
C13—C12—C17	119.14 (11)	C25—C30—H30	120.5
C13—C12—C11	121.70 (11)	C29—C30—H30	120.5
C17—C12—C11	119.16 (11)	C36—C31—C32	121.67 (13)
C14—C13—C12	120.66 (12)	C36—C31—O2	117.97 (12)
C14—C13—H13	119.7	C32—C31—O2	120.34 (12)
C12—C13—H13	119.7	C33—C32—C31	119.06 (15)
C15—C14—C13	118.02 (13)	C33—C32—H32	120.5
C15—C14—H14	121.0	C31—C32—H32	120.5
C13—C14—H14	121.0	C34—C33—C32	120.42 (15)
F1—C15—C14	118.62 (13)	C34—C33—H33	119.8
F1—C15—C16	117.99 (13)	C32—C33—H33	119.8
C14—C15—C16	123.39 (13)	C33—C34—C35	120.23 (15)
C15—C16—C17	118.26 (13)	C33—C34—H34	119.9
C15—C16—H16	120.9	C35—C34—H34	119.9
C17—C16—H16	120.9	C34—C35—C36	120.01 (16)
C16—C17—C12	120.52 (12)	C34—C35—H35	120.0
C16—C17—H17	119.7	C36—C35—H35	120.0
C12—C17—H17	119.7	C31—C36—C35	118.55 (14)
O4—C18—C19	122.34 (11)	C31—C36—H36	120.7
O4—C18—C9	119.96 (11)	C35—C36—H36	120.7
C10—C1—C2—O1	−174.65 (9)	C13—C14—C15—F1	179.56 (13)
C11—C1—C2—O1	−0.77 (15)	C13—C14—C15—C16	−1.0 (2)
C10—C1—C2—C3	−1.47 (17)	F1—C15—C16—C17	−179.61 (13)
C11—C1—C2—C3	172.42 (10)	C14—C15—C16—C17	0.9 (2)
C25—O1—C2—C1	−137.78 (11)	C15—C16—C17—C12	0.2 (2)
C25—O1—C2—C3	48.85 (14)	C13—C12—C17—C16	−1.10 (19)
C1—C2—C3—C4	2.12 (18)	C11—C12—C17—C16	178.19 (12)
O1—C2—C3—C4	175.10 (10)	C8—C9—C18—O4	−109.42 (13)
C2—C3—C4—C5	−0.34 (18)	C10—C9—C18—O4	65.25 (16)
C3—C4—C5—C6	178.22 (11)	C8—C9—C18—C19	67.27 (14)
C3—C4—C5—C10	−1.97 (17)	C10—C9—C18—C19	−118.07 (12)
C4—C5—C6—C7	179.33 (11)	O4—C18—C19—C24	−165.81 (12)
C10—C5—C6—C7	−0.47 (17)	C9—C18—C19—C24	17.59 (17)
C5—C6—C7—C8	1.01 (18)	O4—C18—C19—C20	15.05 (18)
C31—O2—C8—C9	−161.51 (11)	C9—C18—C19—C20	−161.55 (11)
C31—O2—C8—C7	23.62 (16)	C24—C19—C20—C21	−0.71 (19)
C6—C7—C8—C9	−1.41 (18)	C18—C19—C20—C21	178.45 (11)
C6—C7—C8—O2	173.11 (11)	C19—C20—C21—C22	−0.5 (2)
O2—C8—C9—C10	−173.55 (10)	C20—C21—C22—F2	−178.51 (12)
C7—C8—C9—C10	1.23 (17)	C20—C21—C22—C23	1.4 (2)
O2—C8—C9—C18	1.38 (15)	F2—C22—C23—C24	178.84 (12)
C7—C8—C9—C18	176.16 (10)	C21—C22—C23—C24	−1.1 (2)
C8—C9—C10—C5	−0.63 (15)	C22—C23—C24—C19	−0.2 (2)
C18—C9—C10—C5	−175.11 (10)	C20—C19—C24—C23	1.0 (2)
C8—C9—C10—C1	177.13 (10)	C18—C19—C24—C23	−178.09 (12)
C18—C9—C10—C1	2.65 (17)	C2—O1—C25—C26	26.01 (17)
C6—C5—C10—C9	0.26 (15)	C2—O1—C25—C30	−157.08 (11)
C4—C5—C10—C9	−179.54 (10)	C30—C25—C26—C27	1.6 (2)
C6—C5—C10—C1	−177.66 (10)	O1—C25—C26—C27	178.34 (13)
C4—C5—C10—C1	2.53 (15)	C25—C26—C27—C28	−1.1 (2)
C2—C1—C10—C9	−178.62 (10)	C26—C27—C28—C29	−0.3 (2)
C11—C1—C10—C9	7.96 (17)	C27—C28—C29—C30	1.2 (2)
C2—C1—C10—C5	−0.86 (15)	C26—C25—C30—C29	−0.7 (2)
C11—C1—C10—C5	−174.29 (10)	O1—C25—C30—C29	−177.67 (12)
C2—C1—C11—O3	−114.60 (12)	C28—C29—C30—C25	−0.7 (2)
C10—C1—C11—O3	58.99 (15)	C8—O2—C31—C36	−117.82 (13)
C2—C1—C11—C12	63.22 (14)	C8—O2—C31—C32	63.82 (16)
C10—C1—C11—C12	−123.19 (12)	C36—C31—C32—C33	2.7 (2)
O3—C11—C12—C13	−164.21 (12)	O2—C31—C32—C33	−179.01 (12)
C1—C11—C12—C13	18.03 (17)	C31—C32—C33—C34	−1.1 (2)
O3—C11—C12—C17	16.52 (17)	C32—C33—C34—C35	−1.0 (2)
C1—C11—C12—C17	−161.25 (11)	C33—C34—C35—C36	1.6 (3)
C17—C12—C13—C14	1.1 (2)	C32—C31—C36—C35	−2.0 (2)
C11—C12—C13—C14	−178.23 (12)	O2—C31—C36—C35	179.61 (13)
C12—C13—C14—C15	0.0 (2)	C34—C35—C36—C31	−0.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O3i	0.95	2.40	3.3477 (15)	172
C13—H13···Cgii	0.95	2.87	3.6924 (15)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31–C36 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O3i	0.95	2.40	3.3477 (15)	172
C13—H13⋯Cg ii	0.95	2.87	3.6924 (15)	145

Symmetry codes: (i) ; (ii) .