9-(2,4-Di­fluoro­phen­yl)-3,3,6,6-tetra­methyl-3,4,5,6,7,9-hexa­hydro-2H-xanthene-1,8-dione

Rizwana Begum, S.; Hema, R.; Sumathi, G.; Valliappan, R.; Srinivasan, N.

doi:10.1107/S1600536814002761

9-(2,4-Difluorophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione

S. Rizwana Begum, R. Hema, G. Sumathi, R. Valliappan and N. Srinivasan

In the title compound, C₂₃H₂₄F₂O₃, the central pyran ring has a flat-boat conformation, whereas the two fused cyclohexenone rings adopt envelope conformations, with the C atom bearing the dimethyl substituent being the flap atom in each case. The pyran ring mean plane and the difluorophenyl ring are almost normal to each other, making a dihedral angle of 87.55 (4)°. In the crystal, molecules are linked by pairs of C—H

O hydrogen bonds, forming inversion dimers with an R₂²(8) ring motif. The F atom at position 2 on the difluorophenyl ring is disordered over the 2- and 6-positions, and has a refined occupancy ratio of 0.932 (3):0.068 (3).

Read article Similar articles

Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536814002761/su2696sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536814002761/su2696Isup2.hkl Contains datablock I
	Chemical Markup Language (CML) file https://doi.org/10.1107/S1600536814002761/su2696Isup3.cml Supplementary material

CCDC reference: 985439

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
Disorder in main residue
R factor = 0.048
wR factor = 0.147
Data-to-parameter ratio = 25.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          7

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT154_ALERT_1_G The su's on the Cell Angles are Equal ..........    0.00200 Deg.
PLAT180_ALERT_4_G Check Cell Rounding: # of Values Ending with 0 =          3
PLAT199_ALERT_1_G Reported _cell_measurement_temperature ..... (K)        293 Check
PLAT200_ALERT_1_G Reported   _diffrn_ambient_temperature ..... (K)        293 Check
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =          4 Note
PLAT793_ALERT_4_G The Model has Chirality at C7           (Verify)          R
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        115

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   1 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   8 ALERT level G = General information/check it is not something unexpected

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Xanthene is the parent compound of a number of naturally occurring substances and some synthetic dyes. Xanthene derivatives are used as dyes (Hilderbrand & Weissleder, 2007) and are used in medicine as they possess biological properties like antibacterial, antiviral and anti-inflammatory activities (Jonathan et al., 1988). Ehretianone, a quinonoid xanthene was reported to possess anti-snake venom activity (Selvanayagam et al., 1996; Lambert et al., 1997; Poupelin et al., 1978; Hideo, 1981). In view of the importance of the Xanthene derivatives we have synthesized the title compound and report herein on its crystal structure.

In the title molecule, Fig. 1, the pyran ring (O2/C5-C8/C13) has a flat boat conformation [Q = 0.1721 (13) Å, θ = 75.4 (4)° and φ = 186.9 (5)°] with a deviation for atoms O2 [0.1999 (12) Å] and C7 [0.0898 (9) Å] from the mean plane of the other four atoms. The two fused cyclohexenone rings adopt envelope conformations with puckering parameter (Cremer & Pople, 1975) Q = 0.4417 (15) Å, θ = 55.22 (19)° and φ = 116.4 (2)° for ring (C1-C6) and Q = 0.4715 (16) Å, θ = 59.08 (19)° and φ = 179.5 (2)° for ring (C8-C13). Atoms C3 and C11 are the flap atoms being situated out of the mean plane of the respective ring by 0.3118 (9) and 0.3324 (10) Å. The dihedral angle between the mean plane of the central pyran ring (O2/C5-C8/C13) and the difluorophenyl ring (C18-C23) is 87.55 (4)°.

In the crystal, molecules are linked by a pair of C-H···O hydrogen bonds (Fig. 2 and Table 1) forming inversion dimers with an R²₂(8) ring motif (Bernstein et al., 1995).

Related literature top

For the synthesis of xanthenes, see: Vanag & Stankevich (1960); Hilderbrand & Weissleder (2007). For their pharmaceutical properties, see: Jonathan et al. (1988); Lambert et al. (1997); Poupelin et al. (1978); Hideo (1981); Selvanayagam et al. (1996). For related structures, see: Sughanya & Sureshbabu (2012); Sureshbabu & Sughanya (2013). For ring conformation analysis, see: Cremer & Pople (1975). For hydrogen bonding graph-set motifs, see: Bernstein et al. (1995).

Experimental top

5,5-dimethylcyclohexane-1,3-dione (1.15 g, 16 mmol) was treated with 2,4-difluorobenzaldehyde (0.6 g, 8 mmol) in ethanol (10 ml). The reaction mixture was heated for 5 min. After cooling to room temperature, a solid started to separate out. This solid was filtered, dried and then recrystallized from ethanol to yield colourless block-like crystals of the title compound [Yield 0.95 g; 80%].

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The crystal packing of the title compound viewed along the a axis. The C-H···O hydrogen bonds are shown as dashed lines - see Table 1 for details.

9-(2,4-Difluorophenyl)-3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-2H-xanthene-1,8-dione top

Crystal data top

C₂₃H₂₄F₂O₃	Z = 2
M_r = 386.42	F(000) = 408
Triclinic, P1	D_x = 1.288 Mg m⁻³
a = 9.6810 (4) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.4290 (4) Å	Cell parameters from 8029 reflections
c = 11.8840 (5) Å	θ = 2.8–30.5°
α = 69.288 (2)°	µ = 0.10 mm⁻¹
β = 74.895 (2)°	T = 293 K
γ = 63.406 (2)°	Block, colourless
V = 996.03 (7) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	6738 independent reflections
Radiation source: fine-focus sealed tube	4248 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω and φ scan	θ_max = 31.9°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −9→14
T_min = 0.972, T_max = 0.981	k = −10→15
23107 measured reflections	l = −17→17

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H-atom parameters constrained
wR(F²) = 0.147	w = 1/[σ²(F_o²) + (0.0674P)² + 0.1104P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
6738 reflections	Δρ_max = 0.24 e Å⁻³
267 parameters	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₃H₂₄F₂O₃	γ = 63.406 (2)°
M_r = 386.42	V = 996.03 (7) Å³
Triclinic, P1	Z = 2
a = 9.6810 (4) Å	Mo Kα radiation
b = 10.4290 (4) Å	µ = 0.10 mm⁻¹
c = 11.8840 (5) Å	T = 293 K
α = 69.288 (2)°	0.30 × 0.20 × 0.20 mm
β = 74.895 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	6738 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	4248 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.981	R_int = 0.026
23107 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
6738 reflections	Δρ_min = −0.18 e Å⁻³
267 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
F1	0.58177 (9)	0.33825 (10)	0.21213 (9)	0.0634 (3)	0.932 (3)
F1'	1.0560 (15)	0.0461 (17)	0.3554 (14)	0.078 (5)	0.068 (3)
F2	0.72300 (13)	0.44738 (12)	0.50286 (9)	0.0828 (3)
O1	0.84119 (12)	−0.15460 (12)	0.39286 (9)	0.0627 (3)
O2	0.65242 (9)	0.17594 (9)	0.02533 (7)	0.0434 (2)
O3	1.11867 (11)	0.17515 (13)	0.07618 (10)	0.0686 (3)
C1	0.74840 (14)	−0.10446 (13)	0.32037 (11)	0.0420 (3)
C2	0.63396 (15)	−0.17246 (15)	0.33580 (11)	0.0473 (3)
H2A	0.6041	−0.2087	0.4218	0.057*
H2B	0.6856	−0.2578	0.3029	0.057*
C3	0.48605 (14)	−0.06656 (14)	0.27502 (11)	0.0435 (3)
C4	0.53389 (14)	0.00773 (14)	0.14367 (11)	0.0430 (3)
H4A	0.5750	−0.0643	0.0971	0.052*
H4B	0.4424	0.0891	0.1094	0.052*
C5	0.65262 (13)	0.06655 (12)	0.13208 (10)	0.0373 (2)
C6	0.75128 (12)	0.01894 (12)	0.21271 (10)	0.0371 (2)
C7	0.86725 (12)	0.08662 (13)	0.19491 (10)	0.0381 (2)
H7	0.9692	0.0051	0.2097	0.046*
C8	0.87933 (12)	0.17859 (13)	0.06498 (10)	0.0380 (2)
C9	1.01106 (13)	0.22456 (14)	0.01719 (12)	0.0465 (3)
C10	1.01073 (15)	0.32985 (16)	−0.10760 (13)	0.0549 (3)
H10A	1.0736	0.2719	−0.1646	0.066*
H10B	1.0605	0.3935	−0.1099	0.066*
C11	0.85044 (15)	0.42923 (14)	−0.15076 (12)	0.0476 (3)
C12	0.76661 (16)	0.32723 (14)	−0.13191 (11)	0.0467 (3)
H12A	0.6587	0.3880	−0.1454	0.056*
H12B	0.8143	0.2703	−0.1911	0.056*
C13	0.77272 (13)	0.22295 (13)	−0.00826 (10)	0.0386 (2)
C14	0.38365 (17)	0.05031 (19)	0.34291 (15)	0.0644 (4)
H14A	0.4406	0.1052	0.3437	0.097*
H14B	0.3532	0.0020	0.4246	0.097*
H14C	0.2925	0.1174	0.3032	0.097*
C15	0.39565 (18)	−0.15434 (18)	0.27371 (14)	0.0616 (4)
H15A	0.3623	−0.1999	0.3555	0.092*
H15B	0.4616	−0.2302	0.2333	0.092*
H15C	0.3064	−0.0880	0.2316	0.092*
C16	0.75801 (18)	0.54296 (16)	−0.07819 (15)	0.0622 (4)
H16A	0.6554	0.6002	−0.1024	0.093*
H16B	0.8098	0.6083	−0.0931	0.093*
H16C	0.7506	0.4920	0.0066	0.093*
C17	0.8681 (2)	0.51037 (19)	−0.28546 (14)	0.0716 (4)
H17A	0.7671	0.5682	−0.3125	0.107*
H17B	0.9287	0.4387	−0.3308	0.107*
H17C	0.9196	0.5752	−0.2976	0.107*
C18	0.82627 (12)	0.18056 (13)	0.28097 (10)	0.0375 (2)
C19	0.92946 (14)	0.15185 (14)	0.35771 (11)	0.0431 (3)
H19	1.0239	0.0699	0.3589	0.052*	0.932 (3)
C20	0.89720 (16)	0.24020 (16)	0.43221 (12)	0.0514 (3)
H20	0.9683	0.2190	0.4825	0.062*
C21	0.75792 (18)	0.35938 (16)	0.42986 (12)	0.0528 (3)
C22	0.64974 (16)	0.39404 (15)	0.35770 (13)	0.0540 (3)
H22	0.5549	0.4753	0.3580	0.065*
C23	0.68774 (14)	0.30316 (14)	0.28486 (11)	0.0454 (3)
H23	0.6157	0.3255	0.2350	0.054*	0.068 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0438 (5)	0.0656 (6)	0.0797 (7)	0.0015 (4)	−0.0322 (4)	−0.0315 (5)
F1'	0.058 (8)	0.079 (10)	0.093 (11)	−0.011 (7)	−0.035 (7)	−0.023 (8)
F2	0.1159 (8)	0.0833 (7)	0.0739 (6)	−0.0448 (6)	−0.0094 (6)	−0.0435 (5)
O1	0.0698 (6)	0.0637 (6)	0.0568 (6)	−0.0285 (5)	−0.0337 (5)	0.0026 (5)
O2	0.0467 (4)	0.0482 (5)	0.0423 (4)	−0.0277 (4)	−0.0157 (4)	−0.0010 (4)
O3	0.0419 (5)	0.0823 (7)	0.0837 (7)	−0.0312 (5)	−0.0171 (5)	−0.0095 (6)
C1	0.0434 (6)	0.0413 (6)	0.0406 (6)	−0.0136 (5)	−0.0113 (5)	−0.0101 (5)
C2	0.0513 (7)	0.0478 (7)	0.0417 (6)	−0.0244 (6)	−0.0080 (5)	−0.0031 (5)
C3	0.0430 (6)	0.0481 (7)	0.0434 (6)	−0.0237 (5)	−0.0058 (5)	−0.0090 (5)
C4	0.0473 (6)	0.0493 (7)	0.0423 (6)	−0.0274 (5)	−0.0126 (5)	−0.0076 (5)
C5	0.0407 (6)	0.0386 (6)	0.0369 (6)	−0.0189 (5)	−0.0086 (4)	−0.0081 (5)
C6	0.0359 (5)	0.0389 (6)	0.0401 (6)	−0.0151 (5)	−0.0085 (4)	−0.0116 (5)
C7	0.0308 (5)	0.0386 (6)	0.0460 (6)	−0.0105 (4)	−0.0119 (4)	−0.0121 (5)
C8	0.0329 (5)	0.0390 (6)	0.0450 (6)	−0.0139 (4)	−0.0050 (4)	−0.0149 (5)
C9	0.0343 (5)	0.0485 (7)	0.0593 (8)	−0.0164 (5)	−0.0029 (5)	−0.0197 (6)
C10	0.0447 (7)	0.0595 (8)	0.0625 (8)	−0.0281 (6)	0.0038 (6)	−0.0163 (7)
C11	0.0523 (7)	0.0446 (7)	0.0515 (7)	−0.0272 (6)	−0.0044 (6)	−0.0101 (6)
C12	0.0575 (7)	0.0482 (7)	0.0432 (7)	−0.0290 (6)	−0.0103 (5)	−0.0086 (5)
C13	0.0394 (6)	0.0396 (6)	0.0425 (6)	−0.0192 (5)	−0.0056 (5)	−0.0124 (5)
C14	0.0524 (8)	0.0734 (10)	0.0679 (9)	−0.0223 (7)	0.0030 (7)	−0.0303 (8)
C15	0.0641 (9)	0.0684 (9)	0.0636 (9)	−0.0449 (8)	−0.0104 (7)	−0.0041 (7)
C16	0.0664 (9)	0.0459 (7)	0.0798 (10)	−0.0208 (7)	−0.0154 (8)	−0.0208 (7)
C17	0.0896 (12)	0.0714 (10)	0.0602 (9)	−0.0517 (10)	−0.0078 (8)	0.0005 (8)
C18	0.0352 (5)	0.0392 (6)	0.0417 (6)	−0.0159 (5)	−0.0115 (4)	−0.0085 (5)
C19	0.0396 (6)	0.0474 (7)	0.0462 (6)	−0.0201 (5)	−0.0148 (5)	−0.0065 (5)
C20	0.0622 (8)	0.0639 (8)	0.0438 (7)	−0.0379 (7)	−0.0165 (6)	−0.0080 (6)
C21	0.0731 (9)	0.0549 (8)	0.0443 (7)	−0.0352 (7)	−0.0045 (6)	−0.0180 (6)
C22	0.0556 (8)	0.0455 (7)	0.0578 (8)	−0.0127 (6)	−0.0085 (6)	−0.0191 (6)
C23	0.0411 (6)	0.0476 (7)	0.0489 (7)	−0.0130 (5)	−0.0157 (5)	−0.0136 (5)

Geometric parameters (Å, º) top

F1—C23	1.3549 (13)	C11—C16	1.5239 (19)
F1'—C19	1.230 (14)	C11—C17	1.5287 (19)
F2—C21	1.3571 (15)	C11—C12	1.5330 (16)
O1—C1	1.2193 (14)	C12—C13	1.4843 (17)
O2—C5	1.3735 (13)	C12—H12A	0.9700
O2—C13	1.3736 (13)	C12—H12B	0.9700
O3—C9	1.2193 (15)	C14—H14A	0.9600
C1—C6	1.4638 (16)	C14—H14B	0.9600
C1—C2	1.5065 (17)	C14—H14C	0.9600
C2—C3	1.5332 (17)	C15—H15A	0.9600
C2—H2A	0.9700	C15—H15B	0.9600
C2—H2B	0.9700	C15—H15C	0.9600
C3—C14	1.522 (2)	C16—H16A	0.9600
C3—C15	1.5292 (17)	C16—H16B	0.9600
C3—C4	1.5299 (17)	C16—H16C	0.9600
C4—C5	1.4851 (15)	C17—H17A	0.9600
C4—H4A	0.9700	C17—H17B	0.9600
C4—H4B	0.9700	C17—H17C	0.9600
C5—C6	1.3389 (14)	C18—C23	1.3819 (17)
C6—C7	1.5112 (14)	C18—C19	1.3904 (14)
C7—C8	1.5089 (16)	C19—C20	1.3804 (18)
C7—C18	1.5207 (16)	C19—H19	0.9300
C7—H7	0.9800	C20—C21	1.363 (2)
C8—C13	1.3388 (15)	C20—H20	0.9300
C8—C9	1.4684 (15)	C21—C22	1.3685 (19)
C9—C10	1.5009 (19)	C22—C23	1.3730 (18)
C10—C11	1.5310 (19)	C22—H22	0.9300
C10—H10A	0.9700	C23—H23	0.9300
C10—H10B	0.9700

C5—O2—C13	118.21 (8)	C11—C12—H12A	109.2
O1—C1—C6	120.42 (11)	C13—C12—H12B	109.2
O1—C1—C2	121.07 (11)	C11—C12—H12B	109.2
C6—C1—C2	118.44 (9)	H12A—C12—H12B	107.9
C1—C2—C3	114.85 (10)	C8—C13—O2	122.43 (10)
C1—C2—H2A	108.6	C8—C13—C12	125.78 (10)
C3—C2—H2A	108.6	O2—C13—C12	111.79 (9)
C1—C2—H2B	108.6	C3—C14—H14A	109.5
C3—C2—H2B	108.6	C3—C14—H14B	109.5
H2A—C2—H2B	107.5	H14A—C14—H14B	109.5
C14—C3—C15	109.58 (11)	C3—C14—H14C	109.5
C14—C3—C4	110.53 (11)	H14A—C14—H14C	109.5
C15—C3—C4	108.14 (10)	H14B—C14—H14C	109.5
C14—C3—C2	110.07 (11)	C3—C15—H15A	109.5
C15—C3—C2	110.10 (11)	C3—C15—H15B	109.5
C4—C3—C2	108.39 (10)	H15A—C15—H15B	109.5
C5—C4—C3	113.01 (9)	C3—C15—H15C	109.5
C5—C4—H4A	109.0	H15A—C15—H15C	109.5
C3—C4—H4A	109.0	H15B—C15—H15C	109.5
C5—C4—H4B	109.0	C11—C16—H16A	109.5
C3—C4—H4B	109.0	C11—C16—H16B	109.5
H4A—C4—H4B	107.8	H16A—C16—H16B	109.5
C6—C5—O2	123.04 (9)	C11—C16—H16C	109.5
C6—C5—C4	125.44 (10)	H16A—C16—H16C	109.5
O2—C5—C4	111.51 (9)	H16B—C16—H16C	109.5
C5—C6—C1	118.82 (10)	C11—C17—H17A	109.5
C5—C6—C7	122.11 (10)	C11—C17—H17B	109.5
C1—C6—C7	119.06 (9)	H17A—C17—H17B	109.5
C8—C7—C6	108.90 (9)	C11—C17—H17C	109.5
C8—C7—C18	110.47 (9)	H17A—C17—H17C	109.5
C6—C7—C18	113.06 (9)	H17B—C17—H17C	109.5
C8—C7—H7	108.1	C23—C18—C19	115.53 (11)
C6—C7—H7	108.1	C23—C18—C7	122.63 (9)
C18—C7—H7	108.1	C19—C18—C7	121.79 (10)
C13—C8—C9	118.38 (11)	F1'—C19—C20	119.4 (6)
C13—C8—C7	122.62 (10)	F1'—C19—C18	118.0 (7)
C9—C8—C7	118.98 (10)	C20—C19—C18	122.57 (12)
O3—C9—C8	120.69 (12)	C20—C19—H19	118.7
O3—C9—C10	121.52 (11)	C18—C19—H19	118.7
C8—C9—C10	117.76 (10)	C21—C20—C19	117.98 (11)
C9—C10—C11	115.71 (10)	C21—C20—H20	121.0
C9—C10—H10A	108.4	C19—C20—H20	121.0
C11—C10—H10A	108.4	F2—C21—C20	119.12 (12)
C9—C10—H10B	108.4	F2—C21—C22	118.00 (13)
C11—C10—H10B	108.4	C20—C21—C22	122.88 (12)
H10A—C10—H10B	107.4	C21—C22—C23	116.87 (12)
C16—C11—C17	109.55 (12)	C21—C22—H22	121.6
C16—C11—C10	110.27 (11)	C23—C22—H22	121.6
C17—C11—C10	110.20 (12)	F1—C23—C22	117.04 (11)
C16—C11—C12	110.34 (11)	F1—C23—C18	118.79 (11)
C17—C11—C12	109.15 (11)	C22—C23—C18	124.17 (11)
C10—C11—C12	107.29 (10)	C22—C23—H23	117.9
C13—C12—C11	112.16 (10)	C18—C23—H23	117.9
C13—C12—H12A	109.2

O1—C1—C2—C3	155.46 (12)	C9—C10—C11—C16	68.74 (15)
C6—C1—C2—C3	−27.60 (16)	C9—C10—C11—C17	−170.19 (12)
C1—C2—C3—C14	−70.82 (14)	C9—C10—C11—C12	−51.47 (15)
C1—C2—C3—C15	168.27 (11)	C16—C11—C12—C13	−70.88 (14)
C1—C2—C3—C4	50.17 (14)	C17—C11—C12—C13	168.68 (12)
C14—C3—C4—C5	73.46 (13)	C10—C11—C12—C13	49.28 (14)
C15—C3—C4—C5	−166.59 (11)	C9—C8—C13—O2	174.81 (10)
C2—C3—C4—C5	−47.24 (14)	C7—C8—C13—O2	−6.63 (17)
C13—O2—C5—C6	9.76 (16)	C9—C8—C13—C12	−5.94 (18)
C13—O2—C5—C4	−168.91 (10)	C7—C8—C13—C12	172.62 (11)
C3—C4—C5—C6	23.38 (17)	C5—O2—C13—C8	−7.66 (16)
C3—C4—C5—O2	−157.99 (10)	C5—O2—C13—C12	173.00 (10)
O2—C5—C6—C1	−176.36 (10)	C11—C12—C13—C8	−23.44 (18)
C4—C5—C6—C1	2.12 (18)	C11—C12—C13—O2	155.88 (10)
O2—C5—C6—C7	2.50 (18)	C8—C7—C18—C23	63.24 (14)
C4—C5—C6—C7	−179.02 (11)	C6—C7—C18—C23	−59.07 (15)
O1—C1—C6—C5	176.86 (12)	C8—C7—C18—C19	−114.03 (11)
C2—C1—C6—C5	−0.10 (17)	C6—C7—C18—C19	123.66 (11)
O1—C1—C6—C7	−2.04 (17)	C23—C18—C19—F1'	−178.2 (9)
C2—C1—C6—C7	−179.00 (10)	C7—C18—C19—F1'	−0.8 (9)
C5—C6—C7—C8	−14.60 (15)	C23—C18—C19—C20	−0.60 (18)
C1—C6—C7—C8	164.25 (10)	C7—C18—C19—C20	176.85 (11)
C5—C6—C7—C18	108.58 (12)	F1'—C19—C20—C21	177.9 (9)
C1—C6—C7—C18	−72.56 (13)	C18—C19—C20—C21	0.34 (19)
C6—C7—C8—C13	16.67 (15)	C19—C20—C21—F2	179.57 (11)
C18—C7—C8—C13	−108.05 (12)	C19—C20—C21—C22	0.3 (2)
C6—C7—C8—C9	−164.77 (10)	F2—C21—C22—C23	−179.89 (12)
C18—C7—C8—C9	70.50 (12)	C20—C21—C22—C23	−0.6 (2)
C13—C8—C9—O3	−172.78 (12)	C21—C22—C23—F1	−179.17 (12)
C7—C8—C9—O3	8.60 (18)	C21—C22—C23—C18	0.3 (2)
C13—C8—C9—C10	5.27 (17)	C19—C18—C23—F1	179.75 (11)
C7—C8—C9—C10	−173.35 (11)	C7—C18—C23—F1	2.32 (18)
O3—C9—C10—C11	−156.79 (13)	C19—C18—C23—C22	0.26 (19)
C8—C9—C10—C11	25.18 (17)	C7—C18—C23—C22	−177.17 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20···O1ⁱ	0.93	2.38	3.3075 (15)	177

Symmetry code: (i) −x+2, −y, −z+1.