(E)-1-(4,4''-Difluoro-5'-meth-oxy-1,1':3',1''-terphenyl-4'-yl)-3-(6-meth-oxy-naphthalen-2-yl)prop-2-en-1-one.

In the title compound, C(33)H(24)F(2)O(3), the central benzene ring makes dihedral angles of 44.71 (10), 47.80 (10) and 63.68 (9)° with the two fluoro-substituted benzene rings and the naphthalene ring system, respectively. In the crystal, mol-ecules are connected via inter-molecular C-H⋯F and C-H⋯O hydrogen bonds. Furthermore, the crystal structure is stabilized by weak C-H⋯π and π-π inter-actions [centroid-centroid distance = 3.6816 (13) Å].

Related literature

For applications of chalcones, see: Dhar (1981 ▶); Dimmock et al. (1999 ▶); Satyanarayana et al. (2004 ▶); Sarojini et al. (2006 ▶); Liu (2006 ▶); Astruc (2002 ▶). For related structures, see: Samshuddin, Narayana et al. (2011 ▶); Samshuddin, Butcher et al. (2011 ▶); Fun et al. (2010 ▶); Jasinski et al. (2010 ▶); Baktır et al. (2011 ▶).

Experimental

Crystal data

C33H24F2O3

M = 506.52

Monoclinic,

a = 6.9524 (5) Å

b = 33.024 (2) Å

c = 11.6030 (9) Å

β = 107.267 (1)°

V = 2544.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.36 × 0.16 × 0.08 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.967, T max = 0.993

53824 measured reflections

7441 independent reflections

4312 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.180

S = 1.02

7441 reflections

345 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.18 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811047660/is5005sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047660/is5005Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047660/is5005Isup3.cml

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

C33H24F2O3	F(000) = 1056
Mr = 506.52	Dx = 1.322 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7590 reflections
a = 6.9524 (5) Å	θ = 2.5–26.5°
b = 33.024 (2) Å	µ = 0.09 mm−1
c = 11.6030 (9) Å	T = 296 K
β = 107.267 (1)°	Plate, yellow
V = 2544.0 (3) Å3	0.36 × 0.16 × 0.08 mm
Z = 4

Bruker APEXII DUO CCD area-detector diffractometer	7441 independent reflections
Radiation source: fine-focus sealed tube	4312 reflections with I > 2σ(I)
graphite	Rint = 0.056
φ and ω scans	θmax = 30.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→9
Tmin = 0.967, Tmax = 0.993	k = −46→46
53824 measured reflections	l = −16→16

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.065	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0622P)2 + 1.2079P] where P = (Fo2 + 2Fc2)/3
7441 reflections	(Δ/σ)max = 0.001
345 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	−0.8506 (3)	0.20150 (6)	0.53664 (18)	0.1044 (6)
F2	0.3881 (2)	−0.01095 (5)	1.20226 (11)	0.0746 (4)
O1	0.0952 (3)	0.04503 (5)	0.43318 (13)	0.0590 (4)
O2	−0.4053 (3)	0.08801 (6)	0.33233 (14)	0.0719 (5)
O3	0.1800 (3)	0.25775 (6)	−0.26009 (18)	0.0868 (6)
C1	0.1517 (4)	0.15151 (8)	0.1660 (2)	0.0595 (6)
H1A	0.2255	0.1415	0.2409	0.071*
C2	0.2463 (4)	0.17487 (8)	0.1012 (2)	0.0616 (6)
H2A	0.3830	0.1805	0.1328	0.074*
C3	0.1381 (4)	0.19040 (7)	−0.0126 (2)	0.0555 (5)
C4	0.2299 (4)	0.21664 (7)	−0.0797 (2)	0.0623 (6)
H4A	0.3652	0.2236	−0.0495	0.075*
C5	0.1152 (4)	0.23119 (8)	−0.1890 (2)	0.0649 (7)
C6	−0.0870 (5)	0.22052 (8)	−0.2378 (2)	0.0725 (7)
H6A	−0.1610	0.2305	−0.3127	0.087*
C7	−0.1757 (4)	0.19549 (8)	−0.1758 (2)	0.0660 (7)
H7A	−0.3102	0.1883	−0.2090	0.079*
C8	−0.0662 (4)	0.18022 (7)	−0.06174 (19)	0.0515 (5)
C9	−0.1600 (4)	0.15587 (7)	0.00749 (19)	0.0555 (5)
H9A	−0.2949	0.1489	−0.0249	0.067*
C10	−0.0563 (4)	0.14246 (7)	0.12064 (18)	0.0521 (5)
C11	−0.1675 (4)	0.12159 (7)	0.19354 (19)	0.0538 (5)
H11A	−0.2986	0.1135	0.1536	0.065*
C12	−0.0997 (4)	0.11319 (7)	0.30973 (19)	0.0537 (5)
H12A	0.0334	0.1194	0.3510	0.064*
C13	−0.2262 (3)	0.09428 (7)	0.37715 (18)	0.0488 (5)
C14	−0.1234 (3)	0.08339 (6)	0.50667 (16)	0.0416 (4)
C15	0.0403 (3)	0.05689 (6)	0.53151 (16)	0.0433 (4)
C16	0.1302 (3)	0.04262 (6)	0.64713 (17)	0.0436 (4)
H16A	0.2366	0.0244	0.6615	0.052*
C17	0.0615 (3)	0.05552 (6)	0.74161 (16)	0.0403 (4)
C18	−0.0957 (3)	0.08305 (6)	0.71871 (17)	0.0424 (4)
H18A	−0.1376	0.0926	0.7827	0.051*
C19	−0.1932 (3)	0.09687 (6)	0.60211 (17)	0.0405 (4)
C20	−0.3657 (3)	0.12534 (6)	0.58344 (17)	0.0441 (4)
C21	−0.3847 (4)	0.15999 (7)	0.5133 (2)	0.0554 (6)
H21A	−0.2871	0.1660	0.4758	0.066*
C22	−0.5472 (4)	0.18581 (8)	0.4985 (2)	0.0678 (7)
H22A	−0.5595	0.2090	0.4514	0.081*
C23	−0.6886 (4)	0.17661 (9)	0.5542 (2)	0.0660 (7)
C24	−0.6756 (3)	0.14343 (8)	0.6256 (2)	0.0608 (6)
H24A	−0.7733	0.1382	0.6637	0.073*
C25	−0.5132 (3)	0.11777 (7)	0.63984 (19)	0.0498 (5)
H25A	−0.5020	0.0949	0.6882	0.060*
C26	0.1510 (3)	0.03850 (6)	0.86460 (16)	0.0418 (4)
C27	0.2048 (3)	0.06306 (7)	0.96664 (18)	0.0496 (5)
H27A	0.1866	0.0909	0.9582	0.060*
C28	0.2850 (3)	0.04658 (8)	1.08059 (18)	0.0548 (6)
H28A	0.3216	0.0630	1.1487	0.066*
C29	0.3089 (3)	0.00566 (8)	1.09028 (18)	0.0520 (5)
C30	0.2575 (3)	−0.01981 (7)	0.9932 (2)	0.0526 (5)
H30A	0.2748	−0.0477	1.0030	0.063*
C31	0.1792 (3)	−0.00303 (7)	0.88003 (18)	0.0479 (5)
H31A	0.1447	−0.0198	0.8127	0.058*
C32	0.3839 (5)	0.26621 (11)	−0.2300 (3)	0.0988 (11)
H32A	0.4117	0.2808	−0.2948	0.148*
H32B	0.4587	0.2413	−0.2164	0.148*
H32C	0.4226	0.2823	−0.1580	0.148*
C33	0.2823 (4)	0.02460 (8)	0.4521 (2)	0.0634 (6)
H33A	0.3081	0.0207	0.3761	0.095*
H33B	0.2765	−0.0012	0.4890	0.095*
H33C	0.3883	0.0406	0.5042	0.095*

	U11	U22	U33	U12	U13	U23
F1	0.0836 (12)	0.1138 (15)	0.1051 (14)	0.0507 (11)	0.0118 (10)	−0.0035 (11)
F2	0.0776 (10)	0.1075 (12)	0.0390 (7)	0.0182 (8)	0.0177 (6)	0.0204 (7)
O1	0.0732 (11)	0.0692 (10)	0.0393 (8)	0.0146 (8)	0.0242 (7)	−0.0037 (7)
O2	0.0602 (11)	0.1037 (14)	0.0438 (9)	−0.0166 (10)	0.0028 (8)	−0.0040 (9)
O3	0.0988 (16)	0.0832 (14)	0.0796 (13)	−0.0171 (12)	0.0282 (12)	0.0173 (11)
C1	0.0659 (15)	0.0654 (15)	0.0455 (12)	0.0092 (12)	0.0137 (11)	0.0029 (11)
C2	0.0569 (14)	0.0661 (15)	0.0601 (14)	0.0036 (12)	0.0150 (11)	−0.0029 (12)
C3	0.0653 (15)	0.0515 (12)	0.0513 (12)	0.0012 (11)	0.0196 (11)	−0.0072 (10)
C4	0.0676 (16)	0.0565 (14)	0.0654 (15)	−0.0064 (12)	0.0239 (12)	−0.0037 (12)
C5	0.0828 (18)	0.0569 (14)	0.0574 (14)	−0.0104 (13)	0.0246 (13)	−0.0021 (11)
C6	0.090 (2)	0.0680 (16)	0.0529 (14)	−0.0142 (15)	0.0108 (13)	0.0043 (12)
C7	0.0745 (17)	0.0665 (16)	0.0499 (13)	−0.0104 (13)	0.0073 (12)	−0.0013 (11)
C8	0.0647 (14)	0.0466 (11)	0.0427 (11)	−0.0016 (10)	0.0153 (10)	−0.0052 (9)
C9	0.0635 (14)	0.0567 (13)	0.0449 (11)	−0.0021 (11)	0.0139 (10)	−0.0034 (10)
C10	0.0687 (15)	0.0493 (12)	0.0399 (10)	0.0042 (11)	0.0185 (10)	−0.0038 (9)
C11	0.0653 (14)	0.0545 (13)	0.0414 (11)	0.0004 (11)	0.0154 (10)	−0.0033 (9)
C12	0.0654 (14)	0.0557 (13)	0.0393 (10)	−0.0033 (11)	0.0145 (10)	−0.0004 (9)
C13	0.0547 (13)	0.0538 (12)	0.0348 (10)	−0.0040 (10)	0.0086 (9)	−0.0044 (8)
C14	0.0445 (11)	0.0459 (11)	0.0334 (9)	−0.0073 (9)	0.0103 (8)	−0.0031 (8)
C15	0.0491 (12)	0.0479 (11)	0.0358 (9)	−0.0054 (9)	0.0172 (8)	−0.0057 (8)
C16	0.0415 (10)	0.0472 (11)	0.0435 (10)	−0.0009 (9)	0.0146 (8)	−0.0022 (8)
C17	0.0419 (10)	0.0450 (10)	0.0345 (9)	−0.0040 (8)	0.0121 (8)	−0.0020 (8)
C18	0.0456 (11)	0.0495 (11)	0.0343 (9)	−0.0035 (9)	0.0152 (8)	−0.0046 (8)
C19	0.0399 (10)	0.0448 (10)	0.0368 (9)	−0.0057 (8)	0.0114 (8)	−0.0031 (8)
C20	0.0434 (11)	0.0460 (11)	0.0390 (10)	−0.0036 (9)	0.0063 (8)	−0.0057 (8)
C21	0.0622 (14)	0.0557 (13)	0.0473 (12)	0.0010 (11)	0.0147 (10)	0.0038 (10)
C22	0.0798 (18)	0.0586 (15)	0.0572 (14)	0.0153 (13)	0.0081 (13)	0.0072 (11)
C23	0.0544 (14)	0.0714 (17)	0.0633 (15)	0.0186 (12)	0.0038 (12)	−0.0123 (13)
C24	0.0444 (13)	0.0715 (16)	0.0651 (15)	−0.0015 (11)	0.0141 (11)	−0.0153 (12)
C25	0.0463 (12)	0.0528 (12)	0.0500 (12)	−0.0052 (10)	0.0135 (9)	−0.0048 (9)
C26	0.0376 (10)	0.0529 (12)	0.0358 (9)	−0.0002 (9)	0.0124 (8)	−0.0006 (8)
C27	0.0533 (12)	0.0537 (12)	0.0412 (10)	−0.0007 (10)	0.0130 (9)	−0.0045 (9)
C28	0.0538 (13)	0.0751 (16)	0.0341 (10)	−0.0004 (11)	0.0109 (9)	−0.0076 (10)
C29	0.0442 (12)	0.0783 (16)	0.0361 (10)	0.0092 (11)	0.0158 (9)	0.0100 (10)
C30	0.0503 (13)	0.0584 (13)	0.0522 (12)	0.0073 (10)	0.0201 (10)	0.0082 (10)
C31	0.0486 (12)	0.0543 (12)	0.0425 (10)	0.0014 (10)	0.0160 (9)	−0.0025 (9)
C32	0.089 (2)	0.095 (2)	0.117 (3)	−0.0174 (19)	0.037 (2)	0.020 (2)
C33	0.0670 (16)	0.0695 (16)	0.0648 (14)	0.0023 (13)	0.0368 (13)	−0.0119 (12)

F1—C23	1.360 (3)	C16—C17	1.386 (3)
F2—C29	1.367 (2)	C16—H16A	0.9300
O1—C15	1.363 (2)	C17—C18	1.385 (3)
O1—C33	1.423 (3)	C17—C26	1.487 (3)
O2—C13	1.216 (3)	C18—C19	1.398 (3)
O3—C5	1.369 (3)	C18—H18A	0.9300
O3—C32	1.384 (4)	C19—C20	1.489 (3)
C1—C2	1.373 (3)	C20—C21	1.387 (3)
C1—C10	1.416 (3)	C20—C25	1.393 (3)
C1—H1A	0.9300	C21—C22	1.385 (3)
C2—C3	1.408 (3)	C21—H21A	0.9300
C2—H2A	0.9300	C22—C23	1.362 (4)
C3—C8	1.406 (3)	C22—H22A	0.9300
C3—C4	1.435 (3)	C23—C24	1.360 (4)
C4—C5	1.369 (4)	C24—C25	1.382 (3)
C4—H4A	0.9300	C24—H24A	0.9300
C5—C6	1.396 (4)	C25—H25A	0.9300
C6—C7	1.358 (4)	C26—C31	1.389 (3)
C6—H6A	0.9300	C26—C27	1.392 (3)
C7—C8	1.409 (3)	C27—C28	1.385 (3)
C7—H7A	0.9300	C27—H27A	0.9300
C8—C9	1.424 (3)	C28—C29	1.362 (3)
C9—C10	1.370 (3)	C28—H28A	0.9300
C9—H9A	0.9300	C29—C30	1.366 (3)
C10—C11	1.476 (3)	C30—C31	1.379 (3)
C11—C12	1.319 (3)	C30—H30A	0.9300
C11—H11A	0.9300	C31—H31A	0.9300
C12—C13	1.478 (3)	C32—H32A	0.9600
C12—H12A	0.9300	C32—H32B	0.9600
C13—C14	1.504 (3)	C32—H32C	0.9600
C14—C15	1.396 (3)	C33—H33A	0.9600
C14—C19	1.407 (3)	C33—H33B	0.9600
C15—C16	1.384 (3)	C33—H33C	0.9600
C15—O1—C33	118.47 (17)	C17—C18—H18A	119.1
C5—O3—C32	118.2 (2)	C19—C18—H18A	119.1
C2—C1—C10	121.2 (2)	C18—C19—C14	118.51 (18)
C2—C1—H1A	119.4	C18—C19—C20	119.03 (17)
C10—C1—H1A	119.4	C14—C19—C20	122.46 (17)
C1—C2—C3	120.6 (2)	C21—C20—C25	117.9 (2)
C1—C2—H2A	119.7	C21—C20—C19	122.60 (19)
C3—C2—H2A	119.7	C25—C20—C19	119.46 (19)
C8—C3—C2	119.2 (2)	C22—C21—C20	120.9 (2)
C8—C3—C4	118.9 (2)	C22—C21—H21A	119.6
C2—C3—C4	121.9 (2)	C20—C21—H21A	119.6
C5—C4—C3	118.9 (2)	C23—C22—C21	118.8 (2)
C5—C4—H4A	120.5	C23—C22—H22A	120.6
C3—C4—H4A	120.5	C21—C22—H22A	120.6
O3—C5—C4	125.3 (3)	F1—C23—C24	118.7 (3)
O3—C5—C6	112.9 (2)	F1—C23—C22	118.5 (3)
C4—C5—C6	121.8 (2)	C24—C23—C22	122.8 (2)
C7—C6—C5	120.0 (2)	C23—C24—C25	118.1 (2)
C7—C6—H6A	120.0	C23—C24—H24A	121.0
C5—C6—H6A	120.0	C25—C24—H24A	121.0
C6—C7—C8	120.8 (3)	C24—C25—C20	121.5 (2)
C6—C7—H7A	119.6	C24—C25—H25A	119.2
C8—C7—H7A	119.6	C20—C25—H25A	119.2
C3—C8—C7	119.6 (2)	C31—C26—C27	118.27 (18)
C3—C8—C9	118.9 (2)	C31—C26—C17	119.97 (17)
C7—C8—C9	121.4 (2)	C27—C26—C17	121.75 (19)
C10—C9—C8	121.6 (2)	C28—C27—C26	120.9 (2)
C10—C9—H9A	119.2	C28—C27—H27A	119.5
C8—C9—H9A	119.2	C26—C27—H27A	119.5
C9—C10—C1	118.5 (2)	C29—C28—C27	118.2 (2)
C9—C10—C11	118.9 (2)	C29—C28—H28A	120.9
C1—C10—C11	122.5 (2)	C27—C28—H28A	120.9
C12—C11—C10	126.5 (2)	C28—C29—C30	123.2 (2)
C12—C11—H11A	116.7	C28—C29—F2	118.8 (2)
C10—C11—H11A	116.7	C30—C29—F2	118.0 (2)
C11—C12—C13	122.8 (2)	C29—C30—C31	118.0 (2)
C11—C12—H12A	118.6	C29—C30—H30A	121.0
C13—C12—H12A	118.6	C31—C30—H30A	121.0
O2—C13—C12	122.69 (19)	C30—C31—C26	121.3 (2)
O2—C13—C14	120.62 (19)	C30—C31—H31A	119.3
C12—C13—C14	116.68 (19)	C26—C31—H31A	119.3
C15—C14—C19	119.10 (17)	O3—C32—H32A	109.5
C15—C14—C13	118.22 (17)	O3—C32—H32B	109.5
C19—C14—C13	122.57 (19)	H32A—C32—H32B	109.5
O1—C15—C16	123.75 (19)	O3—C32—H32C	109.5
O1—C15—C14	114.88 (17)	H32A—C32—H32C	109.5
C16—C15—C14	121.29 (18)	H32B—C32—H32C	109.5
C15—C16—C17	119.99 (19)	O1—C33—H33A	109.5
C15—C16—H16A	120.0	O1—C33—H33B	109.5
C17—C16—H16A	120.0	H33A—C33—H33B	109.5
C18—C17—C16	119.15 (17)	O1—C33—H33C	109.5
C18—C17—C26	120.89 (17)	H33A—C33—H33C	109.5
C16—C17—C26	119.90 (18)	H33B—C33—H33C	109.5
C17—C18—C19	121.88 (18)
C10—C1—C2—C3	−0.1 (4)	C14—C15—C16—C17	−1.8 (3)
C1—C2—C3—C8	−2.8 (4)	C15—C16—C17—C18	−0.7 (3)
C1—C2—C3—C4	176.7 (2)	C15—C16—C17—C26	176.75 (18)
C8—C3—C4—C5	0.5 (3)	C16—C17—C18—C19	2.9 (3)
C2—C3—C4—C5	−178.9 (2)	C26—C17—C18—C19	−174.56 (18)
C32—O3—C5—C4	10.3 (4)	C17—C18—C19—C14	−2.4 (3)
C32—O3—C5—C6	−171.2 (3)	C17—C18—C19—C20	177.87 (18)
C3—C4—C5—O3	177.0 (2)	C15—C14—C19—C18	−0.1 (3)
C3—C4—C5—C6	−1.4 (4)	C13—C14—C19—C18	175.87 (18)
O3—C5—C6—C7	−177.7 (2)	C15—C14—C19—C20	179.54 (18)
C4—C5—C6—C7	0.9 (4)	C13—C14—C19—C20	−4.4 (3)
C5—C6—C7—C8	0.4 (4)	C18—C19—C20—C21	133.8 (2)
C2—C3—C8—C7	−179.8 (2)	C14—C19—C20—C21	−45.9 (3)
C4—C3—C8—C7	0.7 (3)	C18—C19—C20—C25	−44.9 (3)
C2—C3—C8—C9	2.7 (3)	C14—C19—C20—C25	135.4 (2)
C4—C3—C8—C9	−176.8 (2)	C25—C20—C21—C22	−1.0 (3)
C6—C7—C8—C3	−1.2 (4)	C19—C20—C21—C22	−179.8 (2)
C6—C7—C8—C9	176.3 (2)	C20—C21—C22—C23	0.1 (4)
C3—C8—C9—C10	0.4 (3)	C21—C22—C23—F1	−178.2 (2)
C7—C8—C9—C10	−177.1 (2)	C21—C22—C23—C24	1.1 (4)
C8—C9—C10—C1	−3.4 (3)	F1—C23—C24—C25	178.1 (2)
C8—C9—C10—C11	172.7 (2)	C22—C23—C24—C25	−1.2 (4)
C2—C1—C10—C9	3.2 (3)	C23—C24—C25—C20	0.1 (3)
C2—C1—C10—C11	−172.7 (2)	C21—C20—C25—C24	1.0 (3)
C9—C10—C11—C12	−167.3 (2)	C19—C20—C25—C24	179.72 (19)
C1—C10—C11—C12	8.5 (4)	C18—C17—C26—C31	131.2 (2)
C10—C11—C12—C13	176.3 (2)	C16—C17—C26—C31	−46.3 (3)
C11—C12—C13—O2	−5.7 (4)	C18—C17—C26—C27	−47.6 (3)
C11—C12—C13—C14	175.1 (2)	C16—C17—C26—C27	135.0 (2)
O2—C13—C14—C15	122.6 (2)	C31—C26—C27—C28	0.2 (3)
C12—C13—C14—C15	−58.2 (3)	C17—C26—C27—C28	179.0 (2)
O2—C13—C14—C19	−53.4 (3)	C26—C27—C28—C29	−0.4 (3)
C12—C13—C14—C19	125.8 (2)	C27—C28—C29—C30	0.0 (3)
C33—O1—C15—C16	−15.3 (3)	C27—C28—C29—F2	179.95 (19)
C33—O1—C15—C14	167.99 (19)	C28—C29—C30—C31	0.5 (3)
C19—C14—C15—O1	179.04 (17)	F2—C29—C30—C31	−179.43 (19)
C13—C14—C15—O1	2.8 (3)	C29—C30—C31—C26	−0.7 (3)
C19—C14—C15—C16	2.3 (3)	C27—C26—C31—C30	0.3 (3)
C13—C14—C15—C16	−173.92 (19)	C17—C26—C31—C30	−178.50 (19)
O1—C15—C16—C17	−178.33 (19)

Cg1, Cg3 and Cg4 are the centroids of the C1–C3/C8–C10, C14–C19 and C20–C25 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C28—H28A···O2i	0.93	2.53	3.363 (3)	148.
C32—H32C···F1ii	0.96	2.40	3.275 (4)	152.
C33—H33A···F2iii	0.96	2.48	3.404 (3)	162.
C32—H32A···Cg1iv	0.96	2.82	3.767 (4)	168.
C24—H24A···Cg3v	0.93	2.83	3.461 (3)	126.
C33—H33B···Cg3vi	0.96	2.91	3.556 (3)	126.
C7—H7A···Cg4iii	0.93	2.85	3.548 (3)	133.

Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg3 and Cg4 are the centroids of the C1–C3/C8–C10, C14–C19 and C20–C25 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28A⋯O2i	0.93	2.53	3.363 (3)	148
C32—H32C⋯F1ii	0.96	2.40	3.275 (4)	152
C33—H33A⋯F2iii	0.96	2.48	3.404 (3)	162
C32—H32A⋯Cg1iv	0.96	2.82	3.767 (4)	168
C24—H24A⋯Cg3v	0.93	2.83	3.461 (3)	126
C33—H33B⋯Cg3vi	0.96	2.91	3.556 (3)	126
C7—H7A⋯Cg4iii	0.93	2.85	3.548 (3)	133

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .