2-(2-Fluoro­phen­yl)-3-hy­droxy-4H-chromen-4-one

Koh, D.

doi:10.1107/S2414314618013329

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 9| September 2018| x181332

https://doi.org/10.1107/S2414314618013329

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2-(2-Fluorophenyl)-3-hydroxy-4H-chromen-4-one

Dongsoo Koh ^a ^*

^aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
^*Correspondence e-mail: dskoh@dongduk.ac.kr

Edited by K. Fejfarova, Institute of Biotechnology CAS, Czech Republic (Received 30 August 2018; accepted 18 September 2018; online 21 September 2018)

The asymmetric unit of the title compound, C₁₅H₉FO₃, contains two independent molecules in which the fluorine-substituted benzene ring is twisted by 47.64 (3) and 56.02 (4)° relative to the 4H-chromenon skeleton. The hydroxyl group in each molecule is tilted from 4H-chromenon skeleton by 24.5 (1) and 16.1 (1)°, respectively. In the crystal, pairs of O—H⋯O hydrogen bonds form inversion dimers with an R²₂(10) graph-set motif.

Keywords: crystal structure; flavonol; O—H⋯O hydrogen bonds; inversion dimer.

CCDC reference: 1868441

Structure description

Flavonoids, which include flavones, flavanone, flavonols and isoflavones, are one of the secondary metabolites in plants. Among the flavonoids, flavonols have an unique structure that has a hydroxyl group at the 3-position of the flavone backbone as an enol type. As a result of this characteristic structure, these molecules show a broad spectrum of biological activities (Patel et al., 2018 ; Raffa et al., 2017 ) and have applications as fluorescent probes for sensing and imaging (Serdiuk et al., 2016 ). As a part of our studies on flavonoid derivatives (Lee et al., 2014 ), the title compound was synthesized and its crystal structure was determined.

The title compound has two independent molecules the asymmetric unit (Fig. 1) in which the fluorine-substituted benzene rings are connected at the C8 and C23 positions of the 4H-chromenon skeleton. The dihedral angles between these rings and the 4H-chromenon skeleton are 47.64 (3) and 56.02 (4)°, respectively. As a consequence of the flavonol structure, the hydroxyl groups are attached at the C9 and C24 positions of the 4H-chromenon skeletons and are tilted from 4H-chromenon ring system by 24.5 (1)° (C1/C9/O3/H3A) and 16.1 (1)° (C61/C24/O6/H6A).

Figure 1
The molecular structure of the title compound, showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level.

In the crystal, pairs of intermolecular O—H⋯O hydrogen bonds form inversion dimers with R₂²(10) graph-set motifs (Table 1, Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O4ⁱ	0.83	1.91	2.6813 (18)	154
O6—H6A⋯O1ⁱⁱ	0.83	2.04	2.8112 (18)	154
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Figure 2
Part of the crystal structure with intermolecular hydrogen bonds are shown as dashed lines. For clarity only those H atoms involved in hydrogen bonding are shown.

Examples of other flavonol structures have also been published recently, see Padgett et al. (2018 ) and Narita et al. (2015 ).

Synthesis and crystallization

The starting material, chalcone I, was prepared by previously reported methods (Yoo et al., 2014 ). The final flavonol product was obtained by oxidative cyclization of the I with H₂O₂ in an alkaline methanol medium (Fig. 3).

Figure 3
Synthetic scheme for the preparation of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₉FO₃
M_r	256.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	22.3701 (6), 6.8836 (2), 15.7987 (4)
β (°)	106.0575 (13)
V (Å³)	2337.87 (11)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.19 × 0.14 × 0.10

Data collection
Diffractometer	Bruker PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker 2012 )
T_min, T_max	0.979, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	68936, 5842, 3646
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.134, 1.03
No. of reflections	5842
No. of parameters	345
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.30
Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXS and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1868441

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618013329/ff4028sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618013329/ff4028Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618013329/ff4028Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

2-(2-Fluorophenyl)-3-hydroxy-4H-chromen-4-one top

Crystal data top

C₁₅H₉FO₃	F(000) = 1056
M_r = 256.22	D_x = 1.456 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9839 reflections
a = 22.3701 (6) Å	θ = 2.6–27.2°
b = 6.8836 (2) Å	µ = 0.11 mm⁻¹
c = 15.7987 (4) Å	T = 223 K
β = 106.0575 (13)°	Block, yellow
V = 2337.87 (11) Å³	0.19 × 0.14 × 0.10 mm
Z = 8

Data collection top

Bruker PHOTON 100 CMOS diffractometer	5842 independent reflections
Radiation source: fine-focus sealed tube	3646 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
φ and ω scans	θ_max = 28.4°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker 2012)	h = −29→29
T_min = 0.979, T_max = 0.989	k = −9→9
68936 measured reflections	l = −21→21

Refinement top

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.134	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0553P)² + 0.8816P] where P = (F_o² + 2F_c²)/3
5842 reflections	(Δ/σ)_max = 0.001
345 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

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.

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 > 2sigma(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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.25573 (8)	0.8644 (2)	0.03626 (11)	0.0274 (4)
O1	0.21337 (5)	0.85797 (19)	−0.03333 (8)	0.0372 (3)
C2	0.24556 (7)	0.8811 (2)	0.12298 (10)	0.0261 (3)
C3	0.18533 (8)	0.8880 (2)	0.13403 (12)	0.0324 (4)
H3	0.1504	0.8791	0.0847	0.039*
C4	0.17746 (9)	0.9077 (3)	0.21655 (12)	0.0372 (4)
H4	0.1371	0.9133	0.2237	0.045*
C5	0.22892 (9)	0.9196 (3)	0.28987 (13)	0.0400 (5)
H5	0.2230	0.9312	0.3463	0.048*
C6	0.28829 (9)	0.9144 (3)	0.28110 (12)	0.0367 (4)
H6	0.3230	0.9240	0.3307	0.044*
C7	0.29576 (8)	0.8948 (2)	0.19709 (11)	0.0286 (4)
O2	0.35602 (5)	0.88921 (18)	0.19202 (7)	0.0321 (3)
C8	0.36710 (8)	0.8753 (2)	0.11136 (11)	0.0279 (4)
C9	0.32064 (8)	0.8628 (2)	0.03648 (11)	0.0287 (4)
O3	0.33412 (6)	0.8547 (2)	−0.04188 (8)	0.0413 (3)
H3A	0.3045	0.8987	−0.0811	0.062*
C10	0.43386 (8)	0.8899 (3)	0.11802 (11)	0.0324 (4)
C11	0.46360 (9)	0.7656 (3)	0.07444 (13)	0.0412 (5)
F1	0.43134 (6)	0.61549 (18)	0.02827 (10)	0.0632 (4)
C12	0.52522 (9)	0.7845 (4)	0.07719 (15)	0.0533 (6)
H12	0.5438	0.6974	0.0462	0.064*
C13	0.55925 (10)	0.9320 (4)	0.12567 (15)	0.0577 (6)
H13	0.6013	0.9481	0.1274	0.069*
C14	0.53195 (10)	1.0561 (4)	0.17168 (15)	0.0596 (6)
H14	0.5556	1.1561	0.2056	0.072*
C15	0.46989 (9)	1.0353 (3)	0.16852 (13)	0.0462 (5)
H15	0.4518	1.1205	0.2009	0.055*
C16	0.22946 (8)	0.4205 (2)	0.24636 (11)	0.0308 (4)
O4	0.26839 (6)	0.4421 (2)	0.31850 (8)	0.0430 (3)
C17	0.24559 (8)	0.3890 (2)	0.16460 (11)	0.0291 (4)
C18	0.30774 (8)	0.3875 (3)	0.16103 (13)	0.0362 (4)
H18	0.3402	0.4067	0.2128	0.043*
C19	0.32119 (9)	0.3584 (3)	0.08274 (13)	0.0409 (5)
H19	0.3628	0.3583	0.0807	0.049*
C20	0.27342 (10)	0.3288 (3)	0.00602 (13)	0.0431 (5)
H20	0.2832	0.3087	−0.0475	0.052*
C21	0.21241 (9)	0.3284 (3)	0.00727 (12)	0.0387 (4)
H21	0.1803	0.3077	−0.0447	0.046*
C22	0.19908 (8)	0.3595 (2)	0.08723 (11)	0.0311 (4)
O5	0.13760 (5)	0.35843 (18)	0.08520 (8)	0.0358 (3)
C23	0.12074 (8)	0.3917 (2)	0.16077 (11)	0.0312 (4)
C24	0.16363 (8)	0.4237 (2)	0.23858 (11)	0.0316 (4)
O6	0.14504 (6)	0.4531 (2)	0.31246 (8)	0.0426 (3)
H6A	0.1745	0.4970	0.3520	0.064*
C25	0.05281 (8)	0.3874 (3)	0.14600 (12)	0.0355 (4)
C26	0.01747 (9)	0.2293 (3)	0.10776 (13)	0.0422 (5)
F2	0.04694 (6)	0.07393 (19)	0.08650 (10)	0.0716 (4)
C27	−0.04596 (9)	0.2209 (3)	0.09268 (14)	0.0482 (5)
H27	−0.0684	0.1103	0.0669	0.058*
C28	−0.07580 (9)	0.3772 (3)	0.11595 (14)	0.0487 (5)
H28	−0.1193	0.3750	0.1053	0.058*
C29	−0.04274 (10)	0.5372 (4)	0.15475 (15)	0.0554 (6)
H29	−0.0636	0.6435	0.1708	0.066*
C30	0.02118 (9)	0.5420 (3)	0.17027 (15)	0.0490 (5)
H30	0.0435	0.6514	0.1976	0.059*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0271 (9)	0.0263 (8)	0.0275 (9)	−0.0021 (7)	0.0054 (7)	0.0013 (7)
O1	0.0287 (7)	0.0501 (8)	0.0295 (6)	−0.0063 (6)	0.0026 (5)	−0.0006 (6)
C2	0.0282 (9)	0.0226 (8)	0.0279 (8)	0.0011 (7)	0.0081 (7)	0.0030 (7)
C3	0.0290 (9)	0.0318 (9)	0.0376 (10)	−0.0017 (7)	0.0112 (8)	0.0039 (8)
C4	0.0362 (10)	0.0375 (10)	0.0439 (11)	0.0002 (8)	0.0209 (9)	0.0039 (8)
C5	0.0479 (12)	0.0434 (11)	0.0352 (10)	0.0020 (9)	0.0225 (9)	0.0018 (8)
C6	0.0399 (11)	0.0428 (11)	0.0271 (9)	0.0015 (8)	0.0088 (8)	0.0021 (8)
C7	0.0278 (9)	0.0286 (8)	0.0297 (9)	0.0033 (7)	0.0089 (7)	0.0041 (7)
O2	0.0262 (6)	0.0441 (7)	0.0254 (6)	0.0037 (5)	0.0063 (5)	0.0031 (5)
C8	0.0264 (9)	0.0297 (9)	0.0280 (9)	0.0026 (7)	0.0084 (7)	0.0026 (7)
C9	0.0296 (9)	0.0313 (9)	0.0266 (8)	−0.0002 (7)	0.0102 (7)	−0.0001 (7)
O3	0.0305 (7)	0.0674 (9)	0.0271 (6)	0.0021 (6)	0.0097 (5)	0.0011 (6)
C10	0.0260 (9)	0.0413 (10)	0.0283 (9)	0.0006 (7)	0.0050 (7)	0.0053 (8)
C11	0.0325 (10)	0.0454 (11)	0.0465 (11)	0.0006 (9)	0.0124 (9)	0.0012 (9)
F1	0.0482 (8)	0.0545 (8)	0.0928 (10)	−0.0020 (6)	0.0290 (7)	−0.0240 (7)
C12	0.0358 (11)	0.0753 (16)	0.0522 (13)	0.0082 (11)	0.0182 (10)	0.0014 (12)
C13	0.0268 (10)	0.0963 (19)	0.0498 (13)	−0.0072 (12)	0.0106 (10)	0.0082 (13)
C14	0.0369 (12)	0.0849 (18)	0.0508 (13)	−0.0174 (12)	0.0019 (10)	−0.0093 (12)
C15	0.0332 (11)	0.0613 (13)	0.0406 (11)	−0.0052 (10)	0.0046 (9)	−0.0061 (10)
C16	0.0287 (9)	0.0280 (9)	0.0338 (10)	−0.0002 (7)	0.0054 (8)	−0.0011 (7)
O4	0.0313 (7)	0.0576 (9)	0.0349 (7)	0.0013 (6)	0.0003 (6)	−0.0104 (6)
C17	0.0291 (9)	0.0230 (8)	0.0349 (9)	−0.0001 (7)	0.0080 (7)	0.0013 (7)
C18	0.0322 (10)	0.0305 (9)	0.0455 (11)	−0.0020 (7)	0.0101 (8)	−0.0007 (8)
C19	0.0403 (11)	0.0333 (10)	0.0553 (12)	0.0005 (8)	0.0234 (10)	0.0042 (9)
C20	0.0558 (13)	0.0396 (11)	0.0404 (11)	0.0072 (9)	0.0241 (10)	0.0088 (9)
C21	0.0437 (11)	0.0399 (10)	0.0315 (10)	0.0066 (9)	0.0086 (8)	0.0044 (8)
C22	0.0304 (9)	0.0276 (9)	0.0356 (9)	0.0032 (7)	0.0095 (8)	0.0040 (7)
O5	0.0290 (7)	0.0454 (7)	0.0307 (6)	0.0025 (5)	0.0044 (5)	−0.0013 (6)
C23	0.0277 (9)	0.0319 (9)	0.0328 (9)	0.0009 (7)	0.0065 (7)	−0.0009 (7)
C24	0.0305 (9)	0.0320 (9)	0.0322 (9)	−0.0004 (7)	0.0082 (8)	−0.0005 (7)
O6	0.0311 (7)	0.0640 (9)	0.0334 (7)	−0.0041 (6)	0.0098 (6)	−0.0072 (6)
C25	0.0281 (9)	0.0420 (10)	0.0335 (10)	0.0000 (8)	0.0039 (8)	−0.0002 (8)
C26	0.0314 (10)	0.0439 (11)	0.0471 (11)	0.0032 (8)	0.0040 (9)	−0.0070 (9)
F2	0.0407 (7)	0.0566 (8)	0.1086 (12)	0.0017 (6)	0.0058 (7)	−0.0330 (8)
C27	0.0313 (11)	0.0542 (13)	0.0532 (13)	−0.0062 (9)	0.0019 (9)	−0.0053 (10)
C28	0.0266 (10)	0.0677 (14)	0.0494 (12)	0.0016 (10)	0.0066 (9)	0.0003 (11)
C29	0.0359 (12)	0.0623 (15)	0.0674 (15)	0.0088 (10)	0.0135 (11)	−0.0127 (12)
C30	0.0370 (11)	0.0481 (12)	0.0599 (13)	0.0022 (9)	0.0098 (10)	−0.0133 (10)

Geometric parameters (Å, º) top

C1—O1	1.238 (2)	C16—O4	1.237 (2)
C1—C9	1.451 (2)	C16—C24	1.444 (2)
C1—C2	1.454 (2)	C16—C17	1.450 (2)
C2—C7	1.383 (2)	C17—C22	1.384 (2)
C2—C3	1.406 (2)	C17—C18	1.407 (2)
C3—C4	1.370 (2)	C18—C19	1.366 (3)
C3—H3	0.9400	C18—H18	0.9400
C4—C5	1.391 (3)	C19—C20	1.391 (3)
C4—H4	0.9400	C19—H19	0.9400
C5—C6	1.373 (3)	C20—C21	1.370 (3)
C5—H5	0.9400	C20—H20	0.9400
C6—C7	1.389 (2)	C21—C22	1.392 (2)
C6—H6	0.9400	C21—H21	0.9400
C7—O2	1.3728 (19)	C22—O5	1.367 (2)
O2—C8	1.3671 (19)	O5—C23	1.367 (2)
C8—C9	1.344 (2)	C23—C24	1.352 (2)
C8—C10	1.471 (2)	C23—C25	1.473 (2)
C9—O3	1.3539 (19)	C24—O6	1.358 (2)
O3—H3A	0.8300	O6—H6A	0.8300
C10—C11	1.379 (3)	C25—C26	1.382 (3)
C10—C15	1.390 (3)	C25—C30	1.390 (3)
C11—F1	1.353 (2)	C26—F2	1.346 (2)
C11—C12	1.373 (3)	C26—C27	1.374 (3)
C12—C13	1.369 (3)	C27—C28	1.369 (3)
C12—H12	0.9400	C27—H27	0.9400
C13—C14	1.370 (3)	C28—C29	1.373 (3)
C13—H13	0.9400	C28—H28	0.9400
C14—C15	1.383 (3)	C29—C30	1.383 (3)
C14—H14	0.9400	C29—H29	0.9400
C15—H15	0.9400	C30—H30	0.9400

O1—C1—C9	121.44 (15)	O4—C16—C24	121.22 (16)
O1—C1—C2	123.96 (15)	O4—C16—C17	123.60 (16)
C9—C1—C2	114.56 (14)	C24—C16—C17	115.19 (15)
C7—C2—C3	118.29 (15)	C22—C17—C18	118.26 (16)
C7—C2—C1	120.05 (14)	C22—C17—C16	119.82 (15)
C3—C2—C1	121.64 (15)	C18—C17—C16	121.92 (16)
C4—C3—C2	120.08 (17)	C19—C18—C17	120.32 (18)
C4—C3—H3	120.0	C19—C18—H18	119.8
C2—C3—H3	120.0	C17—C18—H18	119.8
C3—C4—C5	120.24 (17)	C18—C19—C20	120.12 (18)
C3—C4—H4	119.9	C18—C19—H19	119.9
C5—C4—H4	119.9	C20—C19—H19	119.9
C6—C5—C4	121.00 (17)	C21—C20—C19	121.04 (18)
C6—C5—H5	119.5	C21—C20—H20	119.5
C4—C5—H5	119.5	C19—C20—H20	119.5
C5—C6—C7	118.29 (17)	C20—C21—C22	118.48 (18)
C5—C6—H6	120.9	C20—C21—H21	120.8
C7—C6—H6	120.9	C22—C21—H21	120.8
O2—C7—C2	121.94 (14)	O5—C22—C17	121.83 (15)
O2—C7—C6	115.97 (15)	O5—C22—C21	116.39 (16)
C2—C7—C6	122.08 (15)	C17—C22—C21	121.78 (16)
C8—O2—C7	119.38 (13)	C22—O5—C23	119.83 (13)
C9—C8—O2	121.96 (14)	C24—C23—O5	121.57 (15)
C9—C8—C10	126.14 (15)	C24—C23—C25	126.09 (16)
O2—C8—C10	111.76 (14)	O5—C23—C25	112.33 (14)
C8—C9—O3	119.60 (15)	C23—C24—O6	119.78 (15)
C8—C9—C1	122.08 (15)	C23—C24—C16	121.71 (16)
O3—C9—C1	118.28 (14)	O6—C24—C16	118.47 (15)
C9—O3—H3A	109.5	C24—O6—H6A	109.5
C11—C10—C15	116.74 (17)	C26—C25—C30	116.78 (17)
C11—C10—C8	122.85 (17)	C26—C25—C23	121.72 (16)
C15—C10—C8	120.40 (16)	C30—C25—C23	121.50 (17)
F1—C11—C12	118.08 (18)	F2—C26—C27	118.48 (18)
F1—C11—C10	118.95 (16)	F2—C26—C25	118.31 (16)
C12—C11—C10	123.0 (2)	C27—C26—C25	123.19 (18)
C13—C12—C11	119.1 (2)	C28—C27—C26	118.5 (2)
C13—C12—H12	120.5	C28—C27—H27	120.7
C11—C12—H12	120.5	C26—C27—H27	120.7
C12—C13—C14	119.91 (19)	C27—C28—C29	120.53 (19)
C12—C13—H13	120.0	C27—C28—H28	119.7
C14—C13—H13	120.0	C29—C28—H28	119.7
C13—C14—C15	120.4 (2)	C28—C29—C30	120.1 (2)
C13—C14—H14	119.8	C28—C29—H29	119.9
C15—C14—H14	119.8	C30—C29—H29	119.9
C14—C15—C10	120.8 (2)	C29—C30—C25	120.9 (2)
C14—C15—H15	119.6	C29—C30—H30	119.6
C10—C15—H15	119.6	C25—C30—H30	119.6

O1—C1—C2—C7	−177.53 (16)	O4—C16—C17—C22	177.76 (16)
C9—C1—C2—C7	0.3 (2)	C24—C16—C17—C22	−1.7 (2)
O1—C1—C2—C3	1.0 (3)	O4—C16—C17—C18	−2.3 (3)
C9—C1—C2—C3	178.91 (15)	C24—C16—C17—C18	178.18 (16)
C7—C2—C3—C4	−0.1 (2)	C22—C17—C18—C19	0.3 (3)
C1—C2—C3—C4	−178.66 (15)	C16—C17—C18—C19	−179.66 (16)
C2—C3—C4—C5	−0.5 (3)	C17—C18—C19—C20	−0.4 (3)
C3—C4—C5—C6	0.9 (3)	C18—C19—C20—C21	0.1 (3)
C4—C5—C6—C7	−0.8 (3)	C19—C20—C21—C22	0.3 (3)
C3—C2—C7—O2	179.99 (14)	C18—C17—C22—O5	179.88 (15)
C1—C2—C7—O2	−1.4 (2)	C16—C17—C22—O5	−0.2 (2)
C3—C2—C7—C6	0.2 (2)	C18—C17—C22—C21	0.2 (2)
C1—C2—C7—C6	178.81 (16)	C16—C17—C22—C21	−179.93 (16)
C5—C6—C7—O2	−179.60 (15)	C20—C21—C22—O5	179.81 (16)
C5—C6—C7—C2	0.2 (3)	C20—C21—C22—C17	−0.5 (3)
C2—C7—O2—C8	1.9 (2)	C17—C22—O5—C23	1.6 (2)
C6—C7—O2—C8	−178.26 (15)	C21—C22—O5—C23	−178.70 (15)
C7—O2—C8—C9	−1.4 (2)	C22—O5—C23—C24	−0.8 (2)
C7—O2—C8—C10	174.60 (14)	C22—O5—C23—C25	179.34 (14)
O2—C8—C9—O3	178.22 (15)	O5—C23—C24—O6	−178.93 (15)
C10—C8—C9—O3	2.8 (3)	C25—C23—C24—O6	0.9 (3)
O2—C8—C9—C1	0.4 (3)	O5—C23—C24—C16	−1.3 (3)
C10—C8—C9—C1	−175.02 (16)	C25—C23—C24—C16	178.54 (16)
O1—C1—C9—C8	178.06 (16)	O4—C16—C24—C23	−177.03 (17)
C2—C1—C9—C8	0.1 (2)	C17—C16—C24—C23	2.5 (2)
O1—C1—C9—O3	0.2 (3)	O4—C16—C24—O6	0.7 (3)
C2—C1—C9—O3	−177.70 (14)	C17—C16—C24—O6	−179.83 (15)
C9—C8—C10—C11	−49.9 (3)	C24—C23—C25—C26	−124.8 (2)
O2—C8—C10—C11	134.25 (17)	O5—C23—C25—C26	55.0 (2)
C9—C8—C10—C15	128.9 (2)	C24—C23—C25—C30	54.9 (3)
O2—C8—C10—C15	−46.9 (2)	O5—C23—C25—C30	−125.27 (19)
C15—C10—C11—F1	176.51 (17)	C30—C25—C26—F2	−177.54 (18)
C8—C10—C11—F1	−4.6 (3)	C23—C25—C26—F2	2.2 (3)
C15—C10—C11—C12	−2.0 (3)	C30—C25—C26—C27	0.6 (3)
C8—C10—C11—C12	176.81 (19)	C23—C25—C26—C27	−179.67 (19)
F1—C11—C12—C13	−178.09 (19)	F2—C26—C27—C28	178.68 (19)
C10—C11—C12—C13	0.5 (3)	C25—C26—C27—C28	0.5 (3)
C11—C12—C13—C14	1.1 (3)	C26—C27—C28—C29	−1.0 (3)
C12—C13—C14—C15	−0.9 (4)	C27—C28—C29—C30	0.3 (4)
C13—C14—C15—C10	−0.7 (3)	C28—C29—C30—C25	0.9 (4)
C11—C10—C15—C14	2.1 (3)	C26—C25—C30—C29	−1.3 (3)
C8—C10—C15—C14	−176.75 (19)	C23—C25—C30—C29	179.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O4ⁱ	0.83	1.91	2.6813 (18)	154
O6—H6A···O1ⁱⁱ	0.83	2.04	2.8112 (18)	154

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+3/2, z+1/2.

Funding information

The author acknowledges financial support from Dongduk Women's University.

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