Crystal structure of (R)-2'-benz-yloxy-[1,1'-binaphthalen]-2-yl tri-fluoro-methane-sulfonate.

In the title compound, C28H19F3O4S, a new 2'-benz-yloxy (R)-BINOL derivative containing a tri-fluoro-methane-sulfonate group in the 2-position, the planes of the two naphthyl ring systems (r.m.s. deviations = 0.012 and 0.019 Å) are at an angle of 73.36 (2)°, and the planes of the benzyl ring and the naphthyl ring system bound to the ether O atom are at an angle of 75.67 (4)°. In the crystal, mol-ecules are linked via C-H⋯F hydrogen bonds, forming chains propagating along [100]. The chains are linked via a weak C-F⋯π inter-action and weak π-π inter-actions [shortest inter-centroid distance = 3.9158 (12) Å], forming a three-dimensional structure. The absolute structure of the mol-ecule in the crystal was determined by resonant scattering [Flack parameter = 0.02 (6)].

Related literature

For the synthesis of some BINOL derivatives, see, for example: Carrilho et al. (2012 ▶, 2014 ▶). For the synthesis of related binaphthyl-based tri­fluoro­methane­sulfonate derivatives, see: Zeng et al. (2011 ▶); Singer & Buchwald (1999 ▶); Meškovà et al. (2011 ▶); Sälinger & Brückner (2009 ▶); Zheng et al. (2013 ▶). For the use of aryl tri­fluoro­methane­sulfonate derivatives as inter­mediates in Buchwald–Hartwig aminations, see: Louie et al. (1997 ▶); Ahman & Buchwald (1997 ▶); Meadows et al. (2008 ▶). For a review of the synthesis and catalytic applications of binaphthyl-based phosphine and phosphite ligands, see: Sakai et al. (1993 ▶); Yan & Zhang (2006 ▶); Pereira et al. (2013 ▶).

Experimental

Crystal data

C28H19F3O4S

M = 508.49

Orthorhombic,

a = 9.3383 (4) Å

b = 12.3380 (5) Å

c = 20.5893 (8) Å

V = 2372.22 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.19 mm−1

T = 293 K

0.36 × 0.28 × 0.1 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▶) T min = 0.890, T max = 1.000

42588 measured reflections

5367 independent reflections

4373 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.088

S = 1.06

5367 reflections

326 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶)

Absolute structure parameter: 0.02 (6)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and Mercury (Macrae et al. 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814019096/su2775sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814019096/su2775Isup2.hkl

Click here for additional data file.

. DOI: 10.1107/S1600536814019096/su2775fig1.tif

A view of the mol­ecular structure of the title mol­ecule, with atom labelling. Displacement ellipsoids are drawn at the 50% level.

Click here for additional data file.

. DOI: 10.1107/S1600536814019096/su2775fig2.tif

A view along the a axis of the crystal packing of the title compound. The C-H⋯F hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1020770

Additional supporting information: crystallographic information; 3D view; checkCIF report

C28H19F3O4S	F(000) = 1048
Mr = 508.49	Dx = 1.424 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 6182 reflections
a = 9.3383 (4) Å	θ = 2.6–22.2°
b = 12.3380 (5) Å	µ = 0.19 mm−1
c = 20.5893 (8) Å	T = 293 K
V = 2372.22 (17) Å3	Prismatic, colourless
Z = 4	0.36 × 0.28 × 0.1 mm

Bruker APEXII diffractometer	5367 independent reflections
Radiation source: fine-focus sealed tube	4373 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→12
Tmin = 0.890, Tmax = 1.000	k = −15→15
42588 measured reflections	l = −26→26

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.037	w = 1/[σ2(Fo2) + (0.0437P)2 + 0.1954P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.088	(Δ/σ)max = 0.001
S = 1.06	Δρmax = 0.18 e Å−3
5367 reflections	Δρmin = −0.24 e Å−3
326 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraints	Extinction coefficient: 0.0058 (7)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983)
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (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
S1	0.71125 (5)	0.03924 (4)	0.94675 (2)	0.04816 (14)
O1	0.62251 (12)	0.04090 (10)	1.01056 (5)	0.0417 (3)
O2	0.74153 (18)	−0.06979 (12)	0.93075 (8)	0.0706 (4)
O3	0.81614 (18)	0.12109 (14)	0.94647 (8)	0.0759 (5)
C28	0.5709 (3)	0.08085 (18)	0.89039 (11)	0.0641 (6)
F1	0.46451 (16)	0.01259 (12)	0.89093 (7)	0.0829 (4)
F2	0.6254 (2)	0.08254 (15)	0.83119 (7)	0.1095 (6)
F3	0.5251 (2)	0.17688 (12)	0.90464 (9)	0.1210 (8)
C1	0.66233 (18)	0.11054 (13)	1.06373 (8)	0.0381 (4)
C2	0.5916 (2)	0.20964 (15)	1.06794 (9)	0.0471 (5)
H2	0.5246	0.2301	1.0368	0.056*
C3	0.6231 (2)	0.27570 (16)	1.11882 (10)	0.0533 (5)
H3	0.5767	0.3421	1.1227	0.064*
C4	0.7249 (2)	0.24510 (14)	1.16576 (9)	0.0462 (4)
C5	0.7608 (3)	0.31324 (17)	1.21878 (11)	0.0633 (6)
H5	0.7165	0.3804	1.2229	0.076*
C6	0.8584 (3)	0.2820 (2)	1.26350 (11)	0.0705 (7)
H6	0.8812	0.3281	1.2977	0.085*
C7	0.9252 (3)	0.18142 (19)	1.25880 (10)	0.0664 (6)
H7	0.9915	0.1607	1.2901	0.080*
C8	0.8943 (2)	0.11300 (17)	1.20867 (9)	0.0520 (5)
H8	0.9400	0.0462	1.2061	0.062*
C9	0.7933 (2)	0.14259 (14)	1.16045 (8)	0.0405 (4)
C10	0.76185 (18)	0.07382 (13)	1.10677 (8)	0.0362 (4)
C11	0.83484 (18)	−0.03262 (14)	1.09688 (8)	0.0361 (4)
C12	0.97941 (18)	−0.03635 (14)	1.07440 (8)	0.0368 (4)
C13	1.0607 (2)	0.05821 (15)	1.06183 (9)	0.0473 (4)
H13	1.0190	0.1260	1.0674	0.057*
C14	1.1994 (2)	0.05104 (18)	1.04172 (10)	0.0588 (5)
H14	1.2512	0.1140	1.0337	0.071*
C15	1.2648 (2)	−0.05005 (19)	1.03296 (10)	0.0604 (5)
H15	1.3602	−0.0538	1.0203	0.072*
C16	1.1901 (2)	−0.14184 (17)	1.04285 (9)	0.0500 (5)
H16	1.2341	−0.2085	1.0361	0.060*
C17	1.04466 (19)	−0.13834 (14)	1.06346 (8)	0.0396 (4)
C18	0.9652 (2)	−0.23321 (15)	1.07409 (9)	0.0447 (4)
H18	1.0073	−0.3002	1.0661	0.054*
C19	0.8274 (2)	−0.22913 (14)	1.09589 (9)	0.0438 (4)
H19	0.7767	−0.2929	1.1031	0.053*
C20	0.76214 (18)	−0.12812 (13)	1.10741 (8)	0.0374 (4)
O4	0.62534 (13)	−0.11801 (10)	1.13046 (7)	0.0486 (3)
C21	0.5362 (2)	−0.21227 (16)	1.13402 (10)	0.0506 (5)
H21A	0.5492	−0.2543	1.0946	0.061*
H21B	0.4370	−0.1892	1.1354	0.061*
C22	0.56468 (19)	−0.28464 (15)	1.19158 (9)	0.0432 (4)
C23	0.4871 (2)	−0.37900 (17)	1.19706 (11)	0.0568 (5)
H23	0.4214	−0.3971	1.1649	0.068*
C24	0.5055 (3)	−0.44718 (18)	1.24960 (12)	0.0673 (6)
H24	0.4516	−0.5103	1.2529	0.081*
C25	0.6022 (3)	−0.42192 (19)	1.29639 (11)	0.0657 (6)
H25	0.6146	−0.4678	1.3318	0.079*
C26	0.6814 (3)	−0.32918 (19)	1.29156 (11)	0.0654 (6)
H26	0.7486	−0.3125	1.3233	0.079*
C27	0.6614 (2)	−0.25998 (17)	1.23930 (10)	0.0543 (5)
H27	0.7141	−0.1962	1.2366	0.065*

	U11	U22	U33	U12	U13	U23
S1	0.0493 (3)	0.0501 (3)	0.0450 (2)	−0.0092 (2)	0.0044 (2)	−0.0009 (2)
O1	0.0400 (6)	0.0445 (7)	0.0407 (6)	−0.0051 (6)	−0.0015 (5)	0.0028 (6)
O2	0.0793 (10)	0.0590 (9)	0.0736 (10)	0.0117 (8)	0.0072 (8)	−0.0157 (7)
O3	0.0716 (10)	0.0955 (12)	0.0607 (9)	−0.0437 (9)	0.0134 (8)	−0.0032 (8)
C28	0.0933 (17)	0.0476 (12)	0.0513 (12)	−0.0119 (13)	−0.0123 (12)	0.0061 (10)
F1	0.0779 (9)	0.0843 (10)	0.0867 (9)	−0.0169 (8)	−0.0295 (8)	0.0098 (8)
F2	0.1557 (16)	0.1263 (13)	0.0465 (8)	−0.0335 (13)	−0.0093 (9)	0.0187 (8)
F3	0.193 (2)	0.0576 (9)	0.1125 (13)	0.0383 (11)	−0.0741 (14)	−0.0055 (8)
C1	0.0384 (9)	0.0354 (9)	0.0407 (9)	0.0003 (7)	0.0022 (7)	−0.0006 (7)
C2	0.0448 (10)	0.0429 (10)	0.0536 (11)	0.0117 (9)	−0.0018 (9)	0.0086 (9)
C3	0.0568 (12)	0.0395 (11)	0.0636 (13)	0.0160 (9)	0.0064 (10)	−0.0011 (10)
C4	0.0508 (11)	0.0397 (10)	0.0483 (10)	0.0018 (9)	0.0113 (9)	−0.0030 (8)
C5	0.0801 (16)	0.0489 (12)	0.0609 (13)	0.0017 (11)	0.0130 (12)	−0.0143 (10)
C6	0.0911 (18)	0.0670 (15)	0.0535 (13)	−0.0082 (13)	0.0002 (13)	−0.0184 (11)
C7	0.0761 (16)	0.0744 (15)	0.0486 (12)	0.0002 (13)	−0.0097 (11)	−0.0050 (11)
C8	0.0565 (12)	0.0530 (12)	0.0463 (11)	0.0045 (10)	−0.0041 (9)	−0.0009 (9)
C9	0.0447 (10)	0.0388 (9)	0.0380 (9)	−0.0007 (9)	0.0049 (8)	0.0005 (7)
C10	0.0365 (9)	0.0327 (9)	0.0393 (9)	0.0019 (7)	0.0046 (7)	0.0041 (7)
C11	0.0399 (9)	0.0331 (9)	0.0353 (8)	0.0036 (8)	−0.0011 (7)	0.0023 (7)
C12	0.0389 (9)	0.0370 (9)	0.0345 (8)	0.0014 (8)	−0.0021 (7)	0.0011 (7)
C13	0.0462 (10)	0.0406 (10)	0.0552 (11)	−0.0012 (8)	0.0039 (9)	0.0038 (9)
C14	0.0498 (11)	0.0572 (13)	0.0693 (13)	−0.0108 (11)	0.0071 (10)	0.0057 (10)
C15	0.0407 (10)	0.0726 (15)	0.0679 (13)	0.0028 (11)	0.0122 (9)	0.0018 (11)
C16	0.0450 (11)	0.0527 (12)	0.0524 (11)	0.0110 (9)	0.0071 (9)	−0.0003 (9)
C17	0.0437 (10)	0.0406 (10)	0.0344 (9)	0.0073 (8)	−0.0009 (7)	0.0004 (7)
C18	0.0529 (11)	0.0366 (10)	0.0444 (10)	0.0082 (9)	0.0008 (8)	−0.0018 (8)
C19	0.0525 (11)	0.0326 (10)	0.0463 (10)	−0.0011 (8)	0.0007 (8)	0.0026 (8)
C20	0.0372 (9)	0.0352 (9)	0.0398 (9)	0.0027 (7)	0.0010 (7)	0.0048 (7)
O4	0.0422 (7)	0.0387 (7)	0.0651 (8)	−0.0009 (6)	0.0113 (6)	0.0073 (6)
C21	0.0425 (10)	0.0474 (11)	0.0618 (12)	−0.0080 (9)	−0.0027 (9)	0.0084 (9)
C22	0.0368 (10)	0.0425 (10)	0.0502 (10)	−0.0028 (8)	0.0053 (8)	0.0012 (8)
C23	0.0567 (13)	0.0494 (12)	0.0643 (13)	−0.0165 (10)	0.0002 (10)	0.0014 (10)
C24	0.0769 (15)	0.0464 (12)	0.0785 (15)	−0.0107 (12)	0.0119 (13)	0.0092 (12)
C25	0.0802 (16)	0.0589 (14)	0.0580 (13)	0.0100 (13)	0.0094 (12)	0.0137 (11)
C26	0.0714 (15)	0.0728 (15)	0.0520 (12)	−0.0009 (13)	−0.0048 (11)	0.0065 (11)
C27	0.0580 (12)	0.0529 (12)	0.0521 (11)	−0.0130 (10)	−0.0019 (10)	0.0029 (9)

S1—O3	1.4069 (15)	C13—C14	1.362 (3)
S1—O2	1.4136 (15)	C13—H13	0.9300
S1—O1	1.5535 (12)	C14—C15	1.400 (3)
S1—C28	1.824 (2)	C14—H14	0.9300
O1—C1	1.440 (2)	C15—C16	1.346 (3)
C28—F3	1.293 (3)	C15—H15	0.9300
C28—F1	1.302 (3)	C16—C17	1.423 (3)
C28—F2	1.321 (3)	C16—H16	0.9300
C1—C10	1.362 (2)	C17—C18	1.403 (3)
C1—C2	1.393 (2)	C18—C19	1.363 (3)
C2—C3	1.360 (3)	C18—H18	0.9300
C2—H2	0.9300	C19—C20	1.407 (2)
C3—C4	1.407 (3)	C19—H19	0.9300
C3—H3	0.9300	C20—O4	1.368 (2)
C4—C5	1.418 (3)	O4—C21	1.432 (2)
C4—C9	1.421 (2)	C21—C22	1.508 (3)
C5—C6	1.352 (3)	C21—H21A	0.9700
C5—H5	0.9300	C21—H21B	0.9700
C6—C7	1.392 (3)	C22—C27	1.369 (3)
C6—H6	0.9300	C22—C23	1.376 (3)
C7—C8	1.364 (3)	C23—C24	1.381 (3)
C7—H7	0.9300	C23—H23	0.9300
C8—C9	1.417 (3)	C24—C25	1.357 (3)
C8—H8	0.9300	C24—H24	0.9300
C9—C10	1.424 (2)	C25—C26	1.366 (3)
C10—C11	1.493 (2)	C25—H25	0.9300
C11—C20	1.377 (2)	C26—C27	1.386 (3)
C11—C12	1.428 (2)	C26—H26	0.9300
C12—C13	1.416 (3)	C27—H27	0.9300
C12—C17	1.416 (2)
O3—S1—O2	122.88 (11)	C14—C13—C12	120.78 (18)
O3—S1—O1	111.42 (8)	C14—C13—H13	119.6
O2—S1—O1	108.45 (9)	C12—C13—H13	119.6
O3—S1—C28	107.20 (11)	C13—C14—C15	120.76 (19)
O2—S1—C28	105.27 (11)	C13—C14—H14	119.6
O1—S1—C28	98.69 (10)	C15—C14—H14	119.6
C1—O1—S1	120.87 (10)	C16—C15—C14	120.26 (17)
F3—C28—F1	109.8 (2)	C16—C15—H15	119.9
F3—C28—F2	108.80 (19)	C14—C15—H15	119.9
F1—C28—F2	108.19 (19)	C15—C16—C17	120.95 (18)
F3—C28—S1	110.54 (16)	C15—C16—H16	119.5
F1—C28—S1	111.13 (14)	C17—C16—H16	119.5
F2—C28—S1	108.3 (2)	C18—C17—C12	119.26 (16)
C10—C1—C2	125.14 (16)	C18—C17—C16	121.73 (16)
C10—C1—O1	118.18 (14)	C12—C17—C16	119.00 (17)
C2—C1—O1	116.65 (15)	C19—C18—C17	121.32 (17)
C3—C2—C1	118.13 (17)	C19—C18—H18	119.3
C3—C2—H2	120.9	C17—C18—H18	119.3
C1—C2—H2	120.9	C18—C19—C20	119.78 (17)
C2—C3—C4	120.98 (17)	C18—C19—H19	120.1
C2—C3—H3	119.5	C20—C19—H19	120.1
C4—C3—H3	119.5	O4—C20—C11	115.90 (14)
C3—C4—C5	121.96 (18)	O4—C20—C19	122.91 (15)
C3—C4—C9	119.32 (17)	C11—C20—C19	121.18 (16)
C5—C4—C9	118.71 (19)	C20—O4—C21	119.09 (14)
C6—C5—C4	121.0 (2)	O4—C21—C22	114.75 (16)
C6—C5—H5	119.5	O4—C21—H21A	108.6
C4—C5—H5	119.5	C22—C21—H21A	108.6
C5—C6—C7	120.6 (2)	O4—C21—H21B	108.6
C5—C6—H6	119.7	C22—C21—H21B	108.6
C7—C6—H6	119.7	H21A—C21—H21B	107.6
C8—C7—C6	120.6 (2)	C27—C22—C23	118.46 (18)
C8—C7—H7	119.7	C27—C22—C21	123.30 (17)
C6—C7—H7	119.7	C23—C22—C21	118.22 (17)
C7—C8—C9	120.77 (19)	C22—C23—C24	121.0 (2)
C7—C8—H8	119.6	C22—C23—H23	119.5
C9—C8—H8	119.6	C24—C23—H23	119.5
C8—C9—C4	118.34 (16)	C25—C24—C23	119.9 (2)
C8—C9—C10	121.85 (16)	C25—C24—H24	120.0
C4—C9—C10	119.80 (16)	C23—C24—H24	120.0
C1—C10—C9	116.60 (15)	C24—C25—C26	120.1 (2)
C1—C10—C11	121.02 (15)	C24—C25—H25	120.0
C9—C10—C11	122.37 (15)	C26—C25—H25	120.0
C20—C11—C12	119.31 (16)	C25—C26—C27	120.0 (2)
C20—C11—C10	120.39 (14)	C25—C26—H26	120.0
C12—C11—C10	120.27 (16)	C27—C26—H26	120.0
C13—C12—C17	118.19 (15)	C22—C27—C26	120.6 (2)
C13—C12—C11	122.66 (16)	C22—C27—H27	119.7
C17—C12—C11	119.15 (16)	C26—C27—H27	119.7
O3—S1—O1—C1	−7.53 (15)	C1—C10—C11—C12	104.50 (19)
O2—S1—O1—C1	130.68 (13)	C9—C10—C11—C12	−74.6 (2)
C28—S1—O1—C1	−119.94 (13)	C20—C11—C12—C13	179.35 (16)
O3—S1—C28—F3	−53.6 (2)	C10—C11—C12—C13	1.3 (2)
O2—S1—C28—F3	174.03 (18)	C20—C11—C12—C17	0.0 (2)
O1—S1—C28—F3	62.1 (2)	C10—C11—C12—C17	−178.01 (14)
O3—S1—C28—F1	−175.81 (17)	C17—C12—C13—C14	−2.0 (3)
O2—S1—C28—F1	51.9 (2)	C11—C12—C13—C14	178.62 (18)
O1—S1—C28—F1	−60.08 (18)	C12—C13—C14—C15	0.0 (3)
O3—S1—C28—F2	65.48 (18)	C13—C14—C15—C16	1.6 (3)
O2—S1—C28—F2	−66.86 (17)	C14—C15—C16—C17	−1.2 (3)
O1—S1—C28—F2	−178.79 (15)	C13—C12—C17—C18	−178.51 (17)
S1—O1—C1—C10	−85.42 (17)	C11—C12—C17—C18	0.9 (2)
S1—O1—C1—C2	96.53 (17)	C13—C12—C17—C16	2.4 (2)
C10—C1—C2—C3	−0.1 (3)	C11—C12—C17—C16	−178.21 (16)
O1—C1—C2—C3	177.79 (17)	C15—C16—C17—C18	−179.92 (19)
C1—C2—C3—C4	0.3 (3)	C15—C16—C17—C12	−0.9 (3)
C2—C3—C4—C5	179.2 (2)	C12—C17—C18—C19	−1.2 (3)
C2—C3—C4—C9	−1.3 (3)	C16—C17—C18—C19	177.82 (18)
C3—C4—C5—C6	179.7 (2)	C17—C18—C19—C20	0.7 (3)
C9—C4—C5—C6	0.2 (3)	C12—C11—C20—O4	178.43 (15)
C4—C5—C6—C7	−0.6 (4)	C10—C11—C20—O4	−3.6 (2)
C5—C6—C7—C8	0.6 (4)	C12—C11—C20—C19	−0.5 (2)
C6—C7—C8—C9	−0.2 (4)	C10—C11—C20—C19	177.46 (16)
C7—C8—C9—C4	−0.2 (3)	C18—C19—C20—O4	−178.70 (16)
C7—C8—C9—C10	178.4 (2)	C18—C19—C20—C11	0.2 (3)
C3—C4—C9—C8	−179.31 (18)	C11—C20—O4—C21	171.35 (15)
C5—C4—C9—C8	0.2 (3)	C19—C20—O4—C21	−9.7 (2)
C3—C4—C9—C10	2.1 (3)	C20—O4—C21—C22	79.1 (2)
C5—C4—C9—C10	−178.42 (17)	O4—C21—C22—C27	3.9 (3)
C2—C1—C10—C9	0.9 (3)	O4—C21—C22—C23	−177.56 (17)
O1—C1—C10—C9	−177.00 (14)	C27—C22—C23—C24	0.4 (3)
C2—C1—C10—C11	−178.24 (16)	C21—C22—C23—C24	−178.2 (2)
O1—C1—C10—C11	3.9 (2)	C22—C23—C24—C25	−0.7 (4)
C8—C9—C10—C1	179.60 (17)	C23—C24—C25—C26	0.0 (4)
C4—C9—C10—C1	−1.8 (2)	C24—C25—C26—C27	0.9 (4)
C8—C9—C10—C11	−1.3 (3)	C23—C22—C27—C26	0.6 (3)
C4—C9—C10—C11	177.27 (16)	C21—C22—C27—C26	179.1 (2)
C1—C10—C11—C20	−73.5 (2)	C25—C26—C27—C22	−1.3 (3)
C9—C10—C11—C20	107.46 (19)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···F3i	0.93	2.50	3.357 (2)	153
C28—F3···Cg1ii	1.29 (1)	3.61 (1)	4.632 (3)	136 (1)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C4/C9/C10 ring

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯F3i	0.93	2.50	3.357 (2)	153
C28—F3⋯Cg1ii	1.29 (1)	3.61 (1)	4.632 (3)	136 (1)

Symmetry codes: (i) ; (ii) .