Crystal structure of 1,2-bis­(4-fluoro­phen­yl)-1-hy­droxy-2,3,8-tri­meth­oxy­acenaphthene: formation of a five-membered intra­molecular O—H...O hydrogen-bonded ring

In the crystal of the title compound, the formation of an intra­molecular O–H...O hydrogen bond between the hy­droxy group and the meth­oxy group at the 1,2-positions of the acenaphthene ring core giving rise to a five-membered cyclic organization is observed. In the mol­ecular packing, a pair of non-classical C—H...O hydrogen bonds forms centrosymmetric dimeric structures.

Key indicators

• Single-crystal X-ray study
• T = 193 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.115
• Data-to-parameter ratio = 12.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3       --C4       .        5.6 s.u.
PLAT906_ALERT_3_C Large K Value in the Analysis of Variance ......      2.311 Check
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L=    0.600         57 Report

Alert level G
PLAT005_ALERT_5_G No Embedded Refinement Details Found  in the CIF     Please Do !
PLAT063_ALERT_4_G Crystal Size Possibly too Large for Beam Size ..       0.80 mm
PLAT154_ALERT_1_G The s.u.'s on the Cell Angles are Equal ..(Note)      0.001 Degree
PLAT725_ALERT_2_G D-H     Calc     0.98000, Rep     0.95000 Dev...       0.03 Ang.
              C26      -H26C            1.555   1.555 ........     #   59 Check
PLAT725_ALERT_2_G D-H     Calc     0.98000, Rep     0.95000 Dev...       0.03 Ang.
              C26      -H26C            1.555   1.555 ........     #   59 Check
PLAT725_ALERT_2_G D-H     Calc     0.98000, Rep     0.95000 Dev...       0.03 Ang.
              C26      -H26C            1.555   1.555 ........     #   59 Check
PLAT725_ALERT_2_G D-H     Calc     0.98000, Rep     0.95000 Dev...       0.03 Ang.
              C25      -H25B            1.555   1.555 ........     #   59 Check
PLAT793_ALERT_4_G Model has Chirality at C11         (Centro SPGR)          S Verify
PLAT793_ALERT_4_G Model has Chirality at C18         (Centro SPGR)          R Verify
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          9 Note
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.         13 Info

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 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
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku, 2010); program(s) used to solve structure: SIR2014 (Burla et al., 2007); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1,2-Bis(4-fluorophenyl)-1-hydroxy-2,3,8-trimethoxyacenaphthene

Crystal data

C27H22F2O4	Z = 2
Mr = 448.44	F(000) = 468
Triclinic, P1	Dx = 1.371 Mg m^−3
a = 10.14886 (18) Å	Cu Kα radiation, λ = 1.54187 Å
b = 11.1827 (2) Å	Cell parameters from 15130 reflections
c = 11.6411 (2) Å	θ = 4.1–68.2°
α = 66.724 (1)°	µ = 0.86 mm^−1
β = 77.693 (1)°	T = 193 K
γ = 63.613 (1)°	Plate, colourless
V = 1086.07 (4) Å^3	0.8 × 0.35 × 0.1 mm

Data collection

Rigaku R-AXIS RAPID diffractometer	3743 reflections with I > 2σ(I)
Detector resolution: 10.00 pixels mm^-1	Rint = 0.063
ω scans	θmax = 68.2°, θmin = 4.1°
Absorption correction: numerical (NUMABS; Higashi, 1999)	h = −11→12
Tmin = 0.542, Tmax = 0.918	k = −13→13
40472 measured reflections	l = −13→14
3919 independent reflections

Refinement

Refinement on F^2	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0586P)^2 + 0.398P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.115	(Δ/σ)max < 0.001
S = 1.06	Δρmax = 0.32 e Å^−3
3919 reflections	Δρmin = −0.21 e Å^−3
306 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0290 (13)
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
F1	0.54395 (13)	0.19439 (16)	0.30239 (12)	0.0761 (4)
F2	0.10156 (14)	−0.08720 (11)	0.63826 (10)	0.0606 (3)
O1	0.58174 (13)	0.24840 (15)	0.78038 (13)	0.0578 (4)
O2	−0.16964 (13)	0.39006 (15)	0.92690 (12)	0.0557 (3)
O3	0.21992 (11)	0.51843 (10)	0.68218 (9)	0.0355 (3)
O4	−0.00974 (11)	0.48709 (11)	0.68032 (9)	0.0355 (3)
C1	0.33402 (16)	0.28835 (15)	0.83979 (13)	0.0348 (3)
C2	0.47642 (18)	0.23756 (17)	0.87338 (17)	0.0443 (4)
C3	0.5048 (2)	0.18063 (19)	1.00327 (19)	0.0563 (5)
H3	0.603535	0.140640	1.026987	0.068*
C4	0.3953 (2)	0.18154 (19)	1.09462 (17)	0.0547 (5)
H4A	0.418739	0.145106	1.179868	0.066*
C5	0.1206 (2)	0.25049 (19)	1.14585 (15)	0.0533 (5)
H5	0.130872	0.221041	1.233168	0.064*
C6	−0.0160 (2)	0.30589 (19)	1.10192 (15)	0.0504 (4)
H6	−0.099321	0.317931	1.158771	0.060*
C7	−0.03631 (18)	0.34594 (17)	0.97319 (14)	0.0410 (4)
C8	0.08404 (16)	0.33506 (14)	0.89067 (13)	0.0325 (3)
C9	0.22314 (17)	0.28432 (15)	0.93596 (13)	0.0352 (3)
C10	0.2480 (2)	0.23577 (16)	1.06408 (14)	0.0451 (4)
C11	0.25998 (15)	0.36839 (14)	0.71479 (13)	0.0298 (3)
C12	0.33911 (15)	0.32035 (15)	0.60487 (13)	0.0315 (3)
C13	0.44715 (17)	0.18364 (16)	0.62201 (15)	0.0389 (3)
H13	0.473777	0.119168	0.704339	0.047*
C14	0.51608 (18)	0.14074 (19)	0.52049 (18)	0.0483 (4)
H14	0.591121	0.048181	0.532017	0.058*
C15	0.47354 (18)	0.2349 (2)	0.40290 (17)	0.0498 (4)
C16	0.36465 (19)	0.3690 (2)	0.38148 (15)	0.0475 (4)
H16	0.335172	0.430894	0.299057	0.057*
C17	0.29898 (16)	0.41139 (17)	0.48419 (14)	0.0382 (3)
H17	0.225034	0.504644	0.471534	0.046*
C18	0.09992 (14)	0.35988 (14)	0.75182 (12)	0.0293 (3)
C19	0.09615 (14)	0.23884 (14)	0.72425 (12)	0.0289 (3)
C20	0.06485 (16)	0.26136 (15)	0.60484 (13)	0.0343 (3)
H20	0.042476	0.352859	0.542456	0.041*
C21	0.06587 (18)	0.15193 (17)	0.57558 (14)	0.0403 (4)
H21	0.044205	0.167574	0.494082	0.048*
C22	0.09894 (18)	0.02068 (16)	0.66732 (15)	0.0411 (4)
C23	0.12865 (18)	−0.00576 (16)	0.78620 (15)	0.0428 (4)
H23	0.149917	−0.097429	0.848094	0.051*
C24	0.12699 (16)	0.10486 (15)	0.81439 (13)	0.0356 (3)
H24	0.147274	0.088352	0.896580	0.043*
C25	0.7328 (2)	0.1777 (3)	0.8115 (3)	0.0758 (7)
H25A	0.751122	0.222033	0.860643	0.091*
H25B	0.795464	0.185182	0.734481	0.091*
H25C	0.755334	0.077256	0.860669	0.091*
C26	−0.2991 (2)	0.4337 (2)	1.00169 (19)	0.0586 (5)
H26A	−0.304348	0.350782	1.072245	0.070*
H26B	−0.385404	0.478465	0.951198	0.070*
H26C	−0.297245	0.502043	1.033444	0.070*
C27	0.33921 (18)	0.56172 (17)	0.65522 (16)	0.0439 (4)
H27A	0.393886	0.521162	0.730991	0.053*
H27B	0.300590	0.665657	0.626704	0.053*
H27C	0.405055	0.528052	0.589461	0.053*
H4	0.010 (3)	0.553 (3)	0.677 (2)	0.068 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0604 (7)	0.1262 (11)	0.0743 (8)	−0.0387 (7)	0.0184 (6)	−0.0758 (8)
F2	0.0874 (8)	0.0489 (6)	0.0625 (6)	−0.0347 (6)	−0.0005 (6)	−0.0285 (5)
O1	0.0283 (6)	0.0732 (8)	0.0771 (9)	−0.0168 (6)	−0.0053 (6)	−0.0335 (7)
O2	0.0382 (7)	0.0851 (9)	0.0588 (7)	−0.0323 (6)	0.0186 (5)	−0.0413 (7)
O3	0.0335 (5)	0.0294 (5)	0.0434 (6)	−0.0157 (4)	0.0060 (4)	−0.0127 (4)
O4	0.0296 (5)	0.0296 (5)	0.0409 (6)	−0.0073 (4)	−0.0062 (4)	−0.0086 (4)
C1	0.0348 (8)	0.0331 (7)	0.0382 (8)	−0.0130 (6)	−0.0062 (6)	−0.0124 (6)
C2	0.0350 (8)	0.0431 (8)	0.0583 (10)	−0.0117 (7)	−0.0108 (7)	−0.0209 (7)
C3	0.0528 (11)	0.0467 (9)	0.0707 (12)	−0.0089 (8)	−0.0329 (9)	−0.0188 (8)
C4	0.0758 (13)	0.0452 (9)	0.0445 (9)	−0.0216 (9)	−0.0256 (9)	−0.0084 (7)
C5	0.0902 (14)	0.0503 (10)	0.0277 (7)	−0.0393 (10)	0.0033 (8)	−0.0118 (7)
C6	0.0710 (12)	0.0550 (10)	0.0382 (8)	−0.0397 (9)	0.0172 (8)	−0.0222 (7)
C7	0.0479 (9)	0.0438 (8)	0.0409 (8)	−0.0272 (7)	0.0111 (7)	−0.0203 (7)
C8	0.0371 (8)	0.0320 (7)	0.0318 (7)	−0.0181 (6)	0.0022 (6)	−0.0113 (5)
C9	0.0440 (8)	0.0304 (7)	0.0334 (7)	−0.0175 (6)	−0.0037 (6)	−0.0094 (6)
C10	0.0682 (11)	0.0370 (8)	0.0346 (8)	−0.0246 (8)	−0.0123 (7)	−0.0075 (6)
C11	0.0269 (7)	0.0278 (6)	0.0334 (7)	−0.0116 (5)	−0.0005 (5)	−0.0090 (5)
C12	0.0256 (7)	0.0362 (7)	0.0364 (7)	−0.0160 (6)	0.0027 (5)	−0.0140 (6)
C13	0.0345 (8)	0.0370 (8)	0.0478 (8)	−0.0144 (6)	−0.0003 (6)	−0.0178 (6)
C14	0.0366 (8)	0.0517 (9)	0.0687 (11)	−0.0154 (7)	0.0028 (8)	−0.0377 (9)
C15	0.0387 (9)	0.0788 (12)	0.0558 (10)	−0.0300 (9)	0.0116 (7)	−0.0461 (9)
C16	0.0409 (9)	0.0744 (12)	0.0370 (8)	−0.0315 (8)	0.0033 (6)	−0.0216 (8)
C17	0.0289 (7)	0.0464 (8)	0.0377 (8)	−0.0158 (6)	0.0018 (6)	−0.0136 (6)
C18	0.0257 (7)	0.0291 (6)	0.0294 (7)	−0.0103 (5)	−0.0008 (5)	−0.0074 (5)
C19	0.0220 (6)	0.0314 (7)	0.0315 (7)	−0.0108 (5)	0.0004 (5)	−0.0096 (5)
C20	0.0345 (7)	0.0357 (7)	0.0315 (7)	−0.0161 (6)	−0.0003 (5)	−0.0086 (6)
C21	0.0445 (9)	0.0480 (9)	0.0342 (7)	−0.0222 (7)	0.0007 (6)	−0.0169 (6)
C22	0.0430 (9)	0.0382 (8)	0.0495 (9)	−0.0191 (7)	0.0036 (7)	−0.0222 (7)
C23	0.0472 (9)	0.0303 (7)	0.0461 (9)	−0.0146 (6)	−0.0064 (7)	−0.0075 (6)
C24	0.0361 (8)	0.0343 (7)	0.0346 (7)	−0.0137 (6)	−0.0059 (6)	−0.0084 (6)
C25	0.0308 (10)	0.0853 (15)	0.1151 (19)	−0.0114 (9)	−0.0110 (10)	−0.0478 (14)
C26	0.0476 (10)	0.0519 (10)	0.0647 (11)	−0.0186 (8)	0.0220 (9)	−0.0228 (9)
C27	0.0444 (9)	0.0433 (8)	0.0531 (9)	−0.0272 (7)	0.0110 (7)	−0.0207 (7)

Geometric parameters (Å, º)

F1—C15	1.3637 (18)	C12—C17	1.386 (2)
F2—C22	1.3640 (17)	C13—H13	0.9500
O1—C2	1.359 (2)	C13—C14	1.383 (2)
O1—C25	1.428 (2)	C14—H14	0.9500
O2—C7	1.368 (2)	C14—C15	1.370 (3)
O2—C26	1.414 (2)	C15—C16	1.372 (3)
O3—C11	1.4425 (16)	C16—H16	0.9500
O3—C27	1.4273 (18)	C16—C17	1.387 (2)
O4—C18	1.4166 (16)	C17—H17	0.9500
O4—H4	0.84 (2)	C18—C19	1.5269 (18)
C1—C2	1.378 (2)	C19—C20	1.3917 (19)
C1—C9	1.411 (2)	C19—C24	1.3872 (19)
C1—C11	1.5239 (19)	C20—H20	0.9500
C2—C3	1.427 (3)	C20—C21	1.389 (2)
C3—H3	0.9500	C21—H21	0.9500
C3—C4	1.364 (3)	C21—C22	1.372 (2)
C4—H4A	0.9500	C22—C23	1.367 (2)
C4—C10	1.407 (3)	C23—H23	0.9500
C5—H5	0.9500	C23—C24	1.392 (2)
C5—C6	1.362 (3)	C24—H24	0.9500
C5—C10	1.419 (3)	C25—H25A	0.9800
C6—H6	0.9500	C25—H25B	0.9800
C6—C7	1.417 (2)	C25—H25C	0.9800
C7—C8	1.375 (2)	C26—H26A	0.9800
C8—C9	1.401 (2)	C26—H26B	0.9800
C8—C18	1.5133 (18)	C26—H26C	0.9800
C9—C10	1.408 (2)	C27—H27A	0.9800
C11—C12	1.5141 (19)	C27—H27B	0.9800
C11—C18	1.6248 (18)	C27—H27C	0.9800
C12—C13	1.393 (2)
C2—O1—C25	119.03 (16)	F1—C15—C16	118.41 (17)
C7—O2—C26	118.84 (14)	C14—C15—C16	122.98 (15)
C27—O3—C11	116.01 (11)	C15—C16—H16	121.1
C18—O4—H4	106.2 (16)	C15—C16—C17	117.80 (16)
C2—C1—C9	118.08 (14)	C17—C16—H16	121.1
C2—C1—C11	133.46 (14)	C12—C17—C16	121.32 (15)
C9—C1—C11	108.01 (12)	C12—C17—H17	119.3
O1—C2—C1	117.94 (15)	C16—C17—H17	119.3
O1—C2—C3	123.50 (15)	O4—C18—C8	114.24 (11)
C1—C2—C3	118.53 (16)	O4—C18—C11	110.16 (10)
C2—C3—H3	118.8	O4—C18—C19	106.73 (11)
C4—C3—C2	122.39 (16)	C8—C18—C11	101.96 (10)
C4—C3—H3	118.8	C8—C18—C19	112.03 (11)
C3—C4—H4A	119.6	C19—C18—C11	111.78 (10)
C3—C4—C10	120.78 (15)	C20—C19—C18	119.58 (12)
C10—C4—H4A	119.6	C24—C19—C18	121.77 (12)
C6—C5—H5	119.3	C24—C19—C20	118.63 (13)
C6—C5—C10	121.46 (15)	C19—C20—H20	119.5
C10—C5—H5	119.3	C21—C20—C19	120.95 (13)
C5—C6—H6	119.3	C21—C20—H20	119.5
C5—C6—C7	121.39 (16)	C20—C21—H21	120.8
C7—C6—H6	119.3	C22—C21—C20	118.35 (14)
O2—C7—C6	123.20 (14)	C22—C21—H21	120.8
O2—C7—C8	117.86 (14)	F2—C22—C21	118.38 (14)
C8—C7—C6	118.89 (16)	F2—C22—C23	118.95 (14)
C7—C8—C9	119.25 (13)	C23—C22—C21	122.66 (14)
C7—C8—C18	131.42 (14)	C22—C23—H23	120.8
C9—C8—C18	109.19 (12)	C22—C23—C24	118.42 (14)
C8—C9—C1	112.86 (12)	C24—C23—H23	120.8
C8—C9—C10	123.07 (15)	C19—C24—C23	120.98 (14)
C10—C9—C1	124.07 (15)	C19—C24—H24	119.5
C4—C10—C5	128.23 (15)	C23—C24—H24	119.5
C4—C10—C9	116.01 (16)	O1—C25—H25A	109.5
C9—C10—C5	115.74 (16)	O1—C25—H25B	109.5
O3—C11—C1	109.27 (11)	O1—C25—H25C	109.5
O3—C11—C12	110.59 (11)	H25A—C25—H25B	109.5
O3—C11—C18	101.39 (10)	H25A—C25—H25C	109.5
C1—C11—C18	102.50 (10)	H25B—C25—H25C	109.5
C12—C11—C1	118.16 (11)	O2—C26—H26A	109.5
C12—C11—C18	113.41 (11)	O2—C26—H26B	109.5
C13—C12—C11	121.58 (13)	O2—C26—H26C	109.5
C17—C12—C11	119.66 (12)	H26A—C26—H26B	109.5
C17—C12—C13	118.69 (14)	H26A—C26—H26C	109.5
C12—C13—H13	119.6	H26B—C26—H26C	109.5
C14—C13—C12	120.74 (15)	O3—C27—H27A	109.5
C14—C13—H13	119.6	O3—C27—H27B	109.5
C13—C14—H14	120.8	O3—C27—H27C	109.5
C15—C14—C13	118.43 (16)	H27A—C27—H27B	109.5
C15—C14—H14	120.8	H27A—C27—H27C	109.5
F1—C15—C14	118.61 (17)	H27B—C27—H27C	109.5
F1—C15—C16—C17	−176.86 (14)	C9—C1—C11—O3	87.60 (13)
F2—C22—C23—C24	179.41 (14)	C9—C1—C11—C12	−144.84 (12)
O1—C2—C3—C4	174.48 (16)	C9—C1—C11—C18	−19.37 (14)
O2—C7—C8—C9	−177.25 (13)	C9—C8—C18—O4	−137.95 (12)
O2—C7—C8—C18	−1.9 (2)	C9—C8—C18—C11	−19.14 (13)
O3—C11—C12—C13	148.52 (13)	C9—C8—C18—C19	100.53 (13)
O3—C11—C12—C17	−34.66 (17)	C10—C5—C6—C7	2.6 (3)
O3—C11—C18—O4	31.44 (13)	C11—C1—C2—O1	−5.4 (3)
O3—C11—C18—C8	−90.22 (11)	C11—C1—C2—C3	172.69 (15)
O3—C11—C18—C19	149.93 (10)	C11—C1—C9—C8	8.32 (16)
O4—C18—C19—C20	34.99 (16)	C11—C1—C9—C10	−171.21 (13)
O4—C18—C19—C24	−146.74 (13)	C11—C12—C13—C14	178.65 (13)
C1—C2—C3—C4	−3.5 (3)	C11—C12—C17—C16	−177.26 (13)
C1—C9—C10—C4	−3.6 (2)	C11—C18—C19—C20	−85.53 (14)
C1—C9—C10—C5	175.15 (14)	C11—C18—C19—C24	92.74 (15)
C1—C11—C12—C13	21.59 (19)	C12—C11—C18—O4	−87.12 (13)
C1—C11—C12—C17	−161.59 (13)	C12—C11—C18—C8	151.21 (11)
C1—C11—C18—O4	144.36 (11)	C12—C11—C18—C19	31.37 (15)
C1—C11—C18—C8	22.70 (12)	C12—C13—C14—C15	−1.3 (2)
C1—C11—C18—C19	−97.14 (12)	C13—C12—C17—C16	−0.3 (2)
C2—C1—C9—C8	−178.37 (13)	C13—C14—C15—F1	178.26 (14)
C2—C1—C9—C10	2.1 (2)	C13—C14—C15—C16	−0.8 (3)
C2—C1—C11—O3	−84.26 (19)	C14—C15—C16—C17	2.2 (3)
C2—C1—C11—C12	43.3 (2)	C15—C16—C17—C12	−1.6 (2)
C2—C1—C11—C18	168.77 (16)	C17—C12—C13—C14	1.8 (2)
C2—C3—C4—C10	1.9 (3)	C18—C8—C9—C1	7.86 (16)
C3—C4—C10—C5	−177.04 (17)	C18—C8—C9—C10	−172.60 (13)
C3—C4—C10—C9	1.6 (2)	C18—C11—C12—C13	−98.36 (15)
C5—C6—C7—O2	174.01 (15)	C18—C11—C12—C17	78.45 (15)
C5—C6—C7—C8	−3.3 (2)	C18—C19—C20—C21	177.64 (13)
C6—C5—C10—C4	179.75 (16)	C18—C19—C24—C23	−177.47 (13)
C6—C5—C10—C9	1.2 (2)	C19—C20—C21—C22	−0.2 (2)
C6—C7—C8—C9	0.3 (2)	C20—C19—C24—C23	0.8 (2)
C6—C7—C8—C18	175.57 (14)	C20—C21—C22—F2	−179.28 (13)
C7—C8—C9—C1	−175.85 (13)	C20—C21—C22—C23	1.0 (2)
C7—C8—C9—C10	3.7 (2)	C21—C22—C23—C24	−0.8 (3)
C7—C8—C18—O4	46.4 (2)	C22—C23—C24—C19	−0.1 (2)
C7—C8—C18—C11	165.18 (15)	C24—C19—C20—C21	−0.7 (2)
C7—C8—C18—C19	−75.15 (19)	C25—O1—C2—C1	−170.50 (16)
C8—C9—C10—C4	176.89 (14)	C25—O1—C2—C3	11.5 (3)
C8—C9—C10—C5	−4.3 (2)	C26—O2—C7—C6	17.1 (2)
C8—C18—C19—C20	160.74 (12)	C26—O2—C7—C8	−165.49 (14)
C8—C18—C19—C24	−20.99 (18)	C27—O3—C11—C1	66.72 (15)
C9—C1—C2—O1	−176.62 (13)	C27—O3—C11—C12	−64.99 (15)
C9—C1—C2—C3	1.5 (2)	C27—O3—C11—C18	174.44 (11)

Hydrogen-bond geometry (Å, º)

Cg2, Cg5, Cg8 and Cg9 are the centroids of the rings (C1–C4,C9,C10), (C19–C24), (C1–C10) and (C1–C8,C10,C11,C18), respectively.

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3	0.83 (3)	2.00 (3)	2.5119 (18)	119 (3)
C24—H24···Cg9	0.95	2.90	3.4960 (17)	122
C20—H20···O4^i	0.95	2.49	3.3554 (17)	151
C4—H4A···F1^ii	0.95	2.44	3.189 (3)	135
C26—H26C···Cg2^iii	0.95	2.70	3.614 (2)	155
C26—H26C···Cg8^iii	0.95	2.85	3.747 (2)	153
C26—H26C···Cg9^iii	0.95	2.91	3.848 (2)	160
C25—H25B···Cg5^iv	0.95	2.81	3.527 (3)	131

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z+1; (iii) −x, −y+1, −z+2; (iv) x+1, y, z.