4-Cyano-3-fluoro­phenyl (2E)-3-(4-hept­yloxy-3-methoxy­phen­yl)acrylate

In the title compound, C₂₄H₂₆FNO₄, the two benzene rings are almost perpendicular to one another, with a dihedral angle of 87.7 (1)°. Mol­ecules are linked into two-dimensional layers by non-classical inter­molecular hydrogen-bonding inter­actions. The packing is further stabilized by π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.057
• wR factor = 0.160
• Data-to-parameter ratio = 14.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.82 Ratio

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.74 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C23
PLAT301_ALERT_3_C Main Residue  Disorder .........................       3.00 Perc.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C23    -   C24    ...       1.43 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C2     -   C7     ...       1.37 Ang.
PLAT366_ALERT_2_C Short? C(sp?)-C(sp?) Bond  C6     -   C7     ...       1.37 Ang.
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C1     -   C2     ...       1.44 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
  12 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

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S1. Comment

We have reported the structure of 4-cyano-3-fluorophenyl 4'-isobutoxy-biphenyl-4-carboxylate, (II) (Ren et al., 2005). In our ongoing research into liquid-crystal materials containing fluorine, the title compound, (I), was obtained and its structure was reported here.

The bond lengths and angles in (I) are within normal ranges (Allen et al., 1987), and the values in the 4-cyano-3-flurophenyl group are comparable with those in the related structure 4-cyano-3-fluorophenyl 4'-isobutoxybiphenyl-4-carboxylate (Ren et al., 2005). The 4-heptyloxy-3-methoxy phenyl group, excluding atom C24, is essentially coplanar with the acrylate fragment. This moiety is almost perpendicular to the 4-cyano-3-fluorophenyl group, with a dihedral angle of 87.7 (1)° between the two benzene rings. The C8—C9—C10—C11 torsion angle is 178.9 (2)°, indicating a trans configuration of the double bond. The F atom shows disorder over two positions, with a site occupany of 0.638 (4) for the main component.

There is one intramolecular hydrogen-bond interaction, C10—H10···O1, forming a five-membered ring, which contributes to the planarity of the acrylate group. In the crystal structure, molecules are linked into two-dimensional layers by intermolecular C9—H9···O2ⁱ and C17—H17B···Fⁱⁱ interactions [symmetry codes: (i) 2 − x, 1 − y, 1 − z; (ii) x − 1, y, 1 + z] (Fig. 2 and Table 2). The packing is further stabilized by π–π interactions between the benzene (C2–C7) rings, the distance between the centroids, Cg···Cgⁱⁱⁱ [symmetry code: (iii) 2 − x, −1 − y, −z], being 3.713 Å.

S2. Experimental

To a solution of 3-(4-hydroxy-3-methoxyphenyl)acrylic acid (1.94 g, 0.01 mol) in 17.0% KOH solution (10 ml) was added dropwise 1-bromoheptane (0.54 g, 0.03 mol) in ethanol (30 ml). The mixture was heated under reflux for 24 h and extra KOH solution was added to remove the by-products. The mixture was then acidified to give a white precipitation, which was filtered and recrystallized from ethanol, giving a white precipitate, identified as 4-hydroxy-3-methoxyphenylacrylic acid. This compound (1.46 g) and DCC (1,3-dicyclohexylcarbodiimide, 0.6 g) were dissolved in THF (20 ml), and a solution of 2-fluoro-4-hydroxybenzonitrile (0.68 g) and DMAP (4-dimethylaminopyridine, 0.01 g) in THF (20 ml) was added. The mixture was stirred at room temperature for 24 h and then filtered. Colorless single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an ethyl acetate/petroleum ether (1:4 v/v) solution over a period of 2 d.

S3. Refinement

All H atoms except H3 and H7 were located in difference Fourier maps and constrained to ride on their parent atoms, with C—H distances in the range 0.93–0.97 Å, and with U_iso(H) = 1.2U_eq(C) or U_iso(H) = 1.5U_eq(methyl C).

Computing details

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).

Figures

	Fig. 1. The structure of the compound (I), showing 50% probability displacement ellipsoids and the atom-numbering scheme. The fluorine is disordered over two positions.
	Fig. 2. A view, down the b axis, of the unit cell. Hydrogen bonds are indicated by dashed lines.

4-Cyano-3-fluorophenyl (2E)-3-(4-heptyloxy-3-methoxyphenyl)acrylate

Crystal data

C24H26FNO4	Z = 2
Mr = 411.46	F(000) = 436
Triclinic, P1	Dx = 1.207 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.763 (4) Å	Cell parameters from 2069 reflections
b = 11.207 (5) Å	θ = 2.5–25.9°
c = 13.631 (7) Å	µ = 0.09 mm^−1
α = 82.499 (8)°	T = 293 K
β = 82.269 (8)°	Column, colorless
γ = 75.662 (8)°	0.31 × 0.30 × 0.14 mm
V = 1132.6 (10) Å^3

Data collection

Siemens SMART 1000 CCD area-detector diffractometer	4124 independent reflections
Radiation source: fine-focus sealed tube	3035 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.014
Detector resolution: 8.33 pixels mm^-1	θmax = 25.5°, θmin = 1.9°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −13→13
Tmin = 0.973, Tmax = 0.988	l = −14→16
5944 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0764P)^2 + 0.2038P] where P = (Fo^2 + 2Fc^2)/3
4124 reflections	(Δ/σ)max < 0.001
283 parameters	Δρmax = 0.23 e Å^−3
1 restraint	Δρmin = −0.21 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
F	1.3298 (3)	0.5588 (2)	−0.03105 (17)	0.0942 (10)	0.638 (4)
F'	1.2113 (7)	0.1760 (4)	0.0527 (4)	0.121 (2)	0.362 (4)
O1	0.90084 (18)	0.50358 (15)	0.24027 (11)	0.0740 (5)
O2	1.09918 (18)	0.44984 (17)	0.35172 (11)	0.0805 (5)
O3	0.32486 (16)	0.73331 (13)	0.70325 (10)	0.0618 (4)
O4	0.03389 (16)	0.82917 (13)	0.62448 (10)	0.0581 (4)
N	1.5186 (4)	0.2853 (3)	−0.12883 (19)	0.1189 (9)
C1	1.4108 (3)	0.3189 (3)	−0.06614 (18)	0.0818 (7)
C2	1.2789 (3)	0.3641 (2)	0.01323 (14)	0.0631 (6)
C3	1.1821 (3)	0.2890 (2)	0.07330 (17)	0.0699 (6)
H3	1.2027	0.2061	0.0615	0.070*	0.64
C4	1.0577 (3)	0.3333 (2)	0.15023 (15)	0.0657 (6)
H4	0.9926	0.2821	0.1897	0.066*
C5	1.0326 (2)	0.4545 (2)	0.16688 (14)	0.0594 (5)
C6	1.1255 (3)	0.5322 (2)	0.10843 (17)	0.0679 (6)
H6	1.1071	0.6144	0.1206	0.068*
C7	1.2458 (3)	0.4856 (2)	0.03190 (16)	0.0681 (6)
H7	1.3073	0.5380	−0.0093	0.068*	0.36
C8	0.9499 (2)	0.49779 (18)	0.33385 (14)	0.0538 (5)
C9	0.8024 (2)	0.55344 (18)	0.40399 (14)	0.0528 (5)
H9	0.8242	0.5521	0.4696	0.053*
C10	0.6382 (2)	0.60614 (17)	0.37956 (14)	0.0511 (5)
H10	0.6215	0.6072	0.3131	0.051*
C11	0.4817 (2)	0.66220 (16)	0.44386 (14)	0.0472 (4)
C12	0.4864 (2)	0.66910 (16)	0.54524 (14)	0.0468 (4)
H12	0.5928	0.6366	0.5736	0.047*
C13	0.3353 (2)	0.72345 (16)	0.60375 (13)	0.0461 (4)
C14	0.1740 (2)	0.77489 (16)	0.56066 (14)	0.0468 (4)
C15	0.1680 (2)	0.76596 (18)	0.46207 (15)	0.0561 (5)
H15	0.0614	0.7975	0.4337	0.056*
C16	0.3214 (3)	0.70970 (19)	0.40393 (15)	0.0568 (5)
H16	0.3155	0.7041	0.3370	0.057*
C17	0.4760 (3)	0.6696 (2)	0.75340 (16)	0.0722 (6)
H17A	0.4982	0.5825	0.7476	0.072*
H17B	0.4528	0.6837	0.8224	0.072*
H17C	0.5787	0.6996	0.7240	0.072*
C18	−0.1367 (2)	0.87871 (19)	0.58684 (15)	0.0553 (5)
H18A	−0.1790	0.8133	0.5646	0.055*
H18B	−0.1265	0.9407	0.5310	0.055*
C19	−0.2645 (2)	0.93578 (19)	0.67025 (15)	0.0572 (5)
H19A	−0.2202	1.0010	0.6913	0.057*
H19B	−0.2687	0.8734	0.7264	0.057*
C20	−0.4530 (2)	0.98946 (18)	0.64097 (15)	0.0551 (5)
H20A	−0.4503	1.0567	0.5886	0.055*
H20B	−0.4932	0.9260	0.6145	0.055*
C21	−0.5851 (3)	1.0371 (2)	0.72710 (17)	0.0660 (6)
H21A	−0.5456	1.1016	0.7526	0.066*
H21B	−0.5853	0.9702	0.7799	0.066*
C22	−0.7742 (3)	1.0884 (2)	0.70024 (19)	0.0739 (6)
H22A	−0.7721	1.1520	0.6448	0.074*
H22B	−0.8149	1.0225	0.6777	0.074*
C23	−0.9079 (4)	1.1426 (3)	0.7826 (2)	0.1080 (10)
H23A	−0.8632	1.2045	0.8084	0.108*
H23B	−1.0184	1.1845	0.7548	0.108*
C24	−0.9472 (6)	1.0554 (5)	0.8636 (3)	0.176 (2)
H24A	−0.9556	0.9813	0.8382	0.176*
H24B	−1.0587	1.0904	0.9004	0.176*
H24C	−0.8535	1.0359	0.9065	0.176*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F	0.0773 (15)	0.1154 (19)	0.0876 (17)	−0.0361 (13)	0.0120 (12)	0.0026 (13)
F'	0.152 (5)	0.089 (3)	0.119 (4)	−0.037 (3)	0.039 (3)	−0.042 (3)
O1	0.0449 (8)	0.1055 (12)	0.0572 (9)	0.0140 (7)	−0.0034 (7)	−0.0189 (8)
O2	0.0428 (8)	0.1218 (14)	0.0632 (9)	0.0128 (8)	−0.0066 (7)	−0.0210 (9)
O3	0.0443 (7)	0.0842 (10)	0.0496 (8)	−0.0029 (7)	−0.0028 (6)	−0.0065 (7)
O4	0.0380 (7)	0.0714 (9)	0.0577 (8)	0.0007 (6)	−0.0011 (6)	−0.0113 (7)
N	0.1015 (18)	0.175 (3)	0.0790 (16)	−0.0276 (18)	0.0248 (14)	−0.0541 (17)
C1	0.0722 (16)	0.118 (2)	0.0548 (14)	−0.0161 (15)	0.0007 (12)	−0.0255 (14)
C2	0.0494 (11)	0.0921 (17)	0.0428 (11)	−0.0042 (11)	−0.0050 (9)	−0.0128 (10)
C3	0.0685 (14)	0.0747 (15)	0.0600 (13)	−0.0018 (12)	−0.0045 (11)	−0.0141 (11)
C4	0.0561 (12)	0.0776 (15)	0.0526 (12)	−0.0034 (11)	0.0015 (10)	0.0011 (10)
C5	0.0393 (10)	0.0807 (15)	0.0473 (11)	0.0084 (10)	−0.0056 (8)	−0.0090 (10)
C6	0.0533 (12)	0.0701 (14)	0.0743 (15)	−0.0030 (10)	−0.0022 (11)	−0.0133 (11)
C7	0.0511 (12)	0.0885 (17)	0.0598 (13)	−0.0127 (11)	−0.0026 (10)	−0.0007 (12)
C8	0.0420 (10)	0.0624 (12)	0.0520 (11)	−0.0036 (9)	−0.0021 (8)	−0.0066 (9)
C9	0.0451 (10)	0.0601 (11)	0.0486 (11)	−0.0050 (9)	0.0005 (8)	−0.0080 (9)
C10	0.0473 (10)	0.0513 (11)	0.0513 (11)	−0.0065 (8)	−0.0007 (8)	−0.0070 (8)
C11	0.0394 (10)	0.0446 (10)	0.0535 (11)	−0.0042 (8)	0.0004 (8)	−0.0065 (8)
C12	0.0346 (9)	0.0463 (10)	0.0563 (11)	−0.0057 (7)	−0.0039 (8)	−0.0021 (8)
C13	0.0399 (9)	0.0482 (10)	0.0481 (10)	−0.0096 (8)	−0.0008 (8)	−0.0031 (8)
C14	0.0357 (9)	0.0478 (10)	0.0523 (11)	−0.0045 (8)	0.0028 (8)	−0.0064 (8)
C15	0.0382 (10)	0.0652 (12)	0.0588 (12)	0.0013 (9)	−0.0069 (9)	−0.0078 (9)
C16	0.0481 (11)	0.0667 (12)	0.0509 (11)	−0.0029 (9)	−0.0047 (9)	−0.0100 (9)
C17	0.0573 (13)	0.0965 (17)	0.0561 (13)	−0.0054 (12)	−0.0125 (10)	−0.0005 (12)
C18	0.0389 (10)	0.0601 (12)	0.0614 (12)	−0.0026 (9)	−0.0034 (9)	−0.0055 (9)
C19	0.0419 (10)	0.0630 (12)	0.0605 (12)	−0.0016 (9)	−0.0017 (9)	−0.0085 (10)
C20	0.0434 (10)	0.0544 (11)	0.0629 (12)	−0.0025 (8)	−0.0029 (9)	−0.0098 (9)
C21	0.0480 (11)	0.0744 (14)	0.0710 (14)	−0.0023 (10)	−0.0021 (10)	−0.0187 (11)
C22	0.0478 (12)	0.0771 (15)	0.0909 (17)	0.0005 (11)	−0.0032 (11)	−0.0208 (13)
C23	0.0613 (16)	0.144 (3)	0.108 (2)	0.0055 (17)	0.0005 (15)	−0.043 (2)
C24	0.140 (4)	0.261 (6)	0.096 (3)	−0.019 (4)	0.030 (3)	−0.002 (3)

Geometric parameters (Å, º)

F—C7	1.329 (3)	C12—H12	0.9300
F—H7	0.4011	C13—C14	1.413 (2)
F'—C3	1.291 (5)	C14—C15	1.369 (3)
F'—H3	0.3596	C15—C16	1.396 (3)
O1—C8	1.369 (2)	C15—H15	0.9300
O1—C5	1.393 (2)	C16—H16	0.9300
O2—C8	1.193 (2)	C17—H17A	0.9600
O3—C13	1.365 (2)	C17—H17B	0.9600
O3—C17	1.423 (2)	C17—H17C	0.9600
O4—C14	1.366 (2)	C18—C19	1.502 (3)
O4—C18	1.439 (2)	C18—H18A	0.9700
N—C1	1.144 (3)	C18—H18B	0.9700
C1—C2	1.437 (3)	C19—C20	1.524 (3)
C2—C7	1.373 (3)	C19—H19A	0.9700
C2—C3	1.382 (3)	C19—H19B	0.9700
C3—C4	1.381 (3)	C20—C21	1.511 (3)
C3—H3	0.9347	C20—H20A	0.9700
C4—C5	1.368 (3)	C20—H20B	0.9700
C4—H4	0.9300	C21—C22	1.513 (3)
C5—C6	1.375 (3)	C21—H21A	0.9700
C6—C7	1.368 (3)	C21—H21B	0.9700
C6—H6	0.9300	C22—C23	1.503 (3)
C7—H7	0.9322	C22—H22A	0.9700
C8—C9	1.457 (3)	C22—H22B	0.9700
C9—C10	1.332 (3)	C23—C24	1.429 (5)
C9—H9	0.9300	C23—H23A	0.9700
C10—C11	1.455 (3)	C23—H23B	0.9700
C10—H10	0.9300	C24—H24A	0.9600
C11—C16	1.381 (3)	C24—H24B	0.9600
C11—C12	1.400 (3)	C24—H24C	0.9600
C12—C13	1.380 (2)
C8—O1—C5	117.42 (14)	C11—C16—H16	119.4
C13—O3—C17	117.24 (15)	C15—C16—H16	119.4
C14—O4—C18	118.10 (15)	O3—C17—H17A	109.5
N—C1—C2	178.0 (3)	O3—C17—H17B	109.5
C7—C2—C3	117.7 (2)	H17A—C17—H17B	109.5
C7—C2—C1	120.0 (2)	O3—C17—H17C	109.5
C3—C2—C1	122.3 (2)	H17A—C17—H17C	109.5
F'—C3—C4	121.6 (3)	H17B—C17—H17C	109.5
F'—C3—C2	116.8 (3)	O4—C18—C19	107.35 (16)
C4—C3—C2	121.6 (2)	O4—C18—H18A	110.2
C4—C3—H3	119.6	C19—C18—H18A	110.2
C2—C3—H3	118.8	O4—C18—H18B	110.2
C5—C4—C3	118.3 (2)	C19—C18—H18B	110.2
C5—C4—H4	120.8	H18A—C18—H18B	108.5
C3—C4—H4	120.8	C18—C19—C20	112.83 (17)
C4—C5—C6	121.8 (2)	C18—C19—H19A	109.0
C4—C5—O1	119.5 (2)	C20—C19—H19A	109.0
C6—C5—O1	118.5 (2)	C18—C19—H19B	109.0
C7—C6—C5	118.3 (2)	C20—C19—H19B	109.0
C7—C6—H6	120.9	H19A—C19—H19B	107.8
C5—C6—H6	120.9	C21—C20—C19	112.89 (17)
F—C7—C6	120.7 (2)	C21—C20—H20A	109.0
F—C7—C2	116.9 (2)	C19—C20—H20A	109.0
C6—C7—C2	122.3 (2)	C21—C20—H20B	109.0
C6—C7—H7	119.0	C19—C20—H20B	109.0
C2—C7—H7	118.7	H20A—C20—H20B	107.8
O2—C8—O1	120.85 (18)	C20—C21—C22	113.82 (18)
O2—C8—C9	126.48 (18)	C20—C21—H21A	108.8
O1—C8—C9	112.66 (16)	C22—C21—H21A	108.8
C10—C9—C8	123.79 (18)	C20—C21—H21B	108.8
C10—C9—H9	118.1	C22—C21—H21B	108.8
C8—C9—H9	118.1	H21A—C21—H21B	107.7
C9—C10—C11	128.09 (18)	C23—C22—C21	115.5 (2)
C9—C10—H10	116.0	C23—C22—H22A	108.4
C11—C10—H10	116.0	C21—C22—H22A	108.4
C16—C11—C12	118.36 (17)	C23—C22—H22B	108.4
C16—C11—C10	118.98 (17)	C21—C22—H22B	108.4
C12—C11—C10	122.65 (16)	H22A—C22—H22B	107.5
C13—C12—C11	120.98 (16)	C24—C23—C22	115.1 (3)
C13—C12—H12	119.5	C24—C23—H23A	108.5
C11—C12—H12	119.5	C22—C23—H23A	108.5
O3—C13—C12	125.61 (16)	C24—C23—H23B	108.5
O3—C13—C14	114.69 (15)	C22—C23—H23B	108.5
C12—C13—C14	119.70 (17)	H23A—C23—H23B	107.5
O4—C14—C15	125.51 (16)	C23—C24—H24A	109.5
O4—C14—C13	115.01 (16)	C23—C24—H24B	109.5
C15—C14—C13	119.47 (17)	H24A—C24—H24B	109.5
C14—C15—C16	120.20 (17)	C23—C24—H24C	109.5
C14—C15—H15	119.9	H24A—C24—H24C	109.5
C16—C15—H15	119.9	H24B—C24—H24C	109.5
C11—C16—C15	121.24 (18)
C7—C2—C3—F'	178.0 (3)	C9—C10—C11—C12	0.9 (3)
C1—C2—C3—F'	−2.3 (4)	C16—C11—C12—C13	−0.9 (3)
C7—C2—C3—C4	−0.7 (3)	C10—C11—C12—C13	179.73 (16)
C1—C2—C3—C4	179.0 (2)	C17—O3—C13—C12	−7.9 (3)
F'—C3—C4—C5	−179.3 (4)	C17—O3—C13—C14	172.18 (16)
C2—C3—C4—C5	−0.6 (3)	C11—C12—C13—O3	179.00 (17)
C3—C4—C5—C6	1.0 (3)	C11—C12—C13—C14	−1.1 (3)
C3—C4—C5—O1	176.37 (17)	C18—O4—C14—C15	1.8 (3)
C8—O1—C5—C4	91.4 (2)	C18—O4—C14—C13	−177.32 (15)
C8—O1—C5—C6	−93.0 (2)	O3—C13—C14—O4	1.5 (2)
C4—C5—C6—C7	0.0 (3)	C12—C13—C14—O4	−178.39 (15)
O1—C5—C6—C7	−175.43 (17)	O3—C13—C14—C15	−177.61 (17)
C5—C6—C7—F	175.2 (2)	C12—C13—C14—C15	2.5 (3)
C5—C6—C7—C2	−1.4 (3)	O4—C14—C15—C16	179.07 (17)
C3—C2—C7—F	−175.0 (2)	C13—C14—C15—C16	−1.9 (3)
C1—C2—C7—F	5.3 (3)	C12—C11—C16—C15	1.5 (3)
C3—C2—C7—C6	1.7 (3)	C10—C11—C16—C15	−179.10 (17)
C1—C2—C7—C6	−178.0 (2)	C14—C15—C16—C11	−0.1 (3)
C5—O1—C8—O2	−1.7 (3)	C14—O4—C18—C19	−178.32 (15)
C5—O1—C8—C9	179.13 (18)	O4—C18—C19—C20	−178.60 (15)
O2—C8—C9—C10	179.8 (2)	C18—C19—C20—C21	175.11 (18)
O1—C8—C9—C10	−1.0 (3)	C19—C20—C21—C22	−178.77 (18)
C8—C9—C10—C11	178.90 (18)	C20—C21—C22—C23	−177.0 (2)
C9—C10—C11—C16	−178.55 (19)	C21—C22—C23—C24	−67.6 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9···O2^i	0.93	2.58	3.509 (3)	177
C10—H10···O1	0.93	2.35	2.730 (3)	104
C17—H17B···F^ii	0.96	2.51	3.211 (4)	130

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