Synthesis, crystal structure and Hirshfeld surface analysis of 4-(3-hy­droxy-6-meth­oxy-4-oxo-4H-chromen-2-yl)benzaldehyde

Snizhko, A.D.; Dyakonenko, V.V.; Gladkov, E.S.; Kyrychenko, A.V.

doi:10.1107/S2056989026003476

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ISSN: 2056-9890

Volume 82| Part 5| May 2026| Pages 459-462

https://doi.org/10.1107/S2056989026003476

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Synthesis, crystal structure and Hirshfeld surface analysis of 4-(3-hydroxy-6-methoxy-4-oxo-4H-chromen-2-yl)benzaldehyde

Arsenii D. Snizhko,^a,^b Viktoriya V. Dyakonenko,^b,^c ^* Eugene S. Gladkov ^a,^b and Alexander V. Kyrychenko ^a,^b

^aV. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv 61022, Ukraine, ^bInstitute of Functional Materials Chemistry, SSI "Institute for Single Crystals" of National Academy of Sciences of Ukraine, Nauki Ave 60, Kharkiv, 61001, Ukraine, and ^cV. I. Vernadskii Institute of General and Inorganic Chemistry of National Academy of Sciences of Ukraine, Prospect Palladina 32/34, 03680 Kyiv, Ukraine
^*Correspondence e-mail: [email protected]

Edited by A. Briceno, Venezuelan Institute of Scientific Research, Venezuela (Received 30 January 2026; accepted 2 April 2026; online 10 April 2026)

The asymmetric unit of the title compound, C₁₇H₁₂O₅, contains one crystallographically independent molecule featuring a chromenone fragment with hydroxy and methoxy substituents and a benzaldehyde group. Intramolecular O—H⋯O, C—H⋯O hydrogen bonds are observed. In the crystal, molecules are linked by O—H⋯O intermolecular bonds, forming chains along [201]. The Hirshfeld surface analysis shows that the H⋯H and O⋯H/H⋯O contacts dominate the crystal packing with contributions of 34.2% and 27.6%, respectively.

Keywords: crystal structure; flavonol derivatives; chromone; ESIPT (Excited-State Intramolecular Proton Transfer); Hirshfeld surface analysis.

CCDC reference: 2543411

1. Chemical context

Compounds bearing a 3-hydroxy-2-phenyl-chromen-4-one core belong to the family specifically categorized as flavonol derivatives (common name: 3-hydroxyflavones). They feature a chromone (1-benzopyran-4-one) core, which is a privileged scaffold in medicinal chemistry due to its diverse biological activities (Borsari et al., 2016 ). These derivatives, also referred to as 3-hydroxyflavones, can scavenge free radicals and chelate metal ions (Roshal, 2024 ; Mihajlović et al., 2025 ), which is vital in preventing oxidative stress-related diseases.

In 3-hydroxyflavone derivatives, a crucial intramolecular hydrogen bond forms between the 3-hydroxyl group and the 4-oxo (carbonyl, C=O) oxygen. This bond forms a five-membered ring stabilized by a resonance-assisted hydrogen bond and is responsible for excited-state intramolecular proton transfer (ESIPT) (Zhao et al., 2021 ; Pivovarenko, 2023 ; Pivovarenko & Klymchenko, 2024 ). The molecule absorbs light in its enol form but, after the proton jumps, it emits light as a keto form. This keto form has a much lower energy, shifting the emission to much longer wavelengths. ESIPT features can be tuned by C4′ substitutions making it possible to use 3-hydroxyflavones as environment-sensitive fluorescence probes (Pivovarenko, 2023; Snizhko et al., 2025 ; Chepeleva et al., 2023 ; Demidov et al., 2022 ; Kyrychenko & Ladokhin, 2024 ).

The X-ray structures were vital for showing how various electron-donating and electron-withdrawing groups, especially at the C6, C7, and C4′ positions, and steric factors affect the planarity of 3-hydroxyflavones (Etter et al., 1986 ; Shoja et al., 1998 ; Shoja & Sullivan, 1999 ; Wera et al., 2011a ,b ; Narita et al., 2015 ; Koh, 2020 ). Recently, we have demonstrated that the nature and position of substituent groups can significantly influence crystal packing in the solid state, thereby tuning the contributions of intra- and intermolecular hydrogen bonding and the ESIPT behavior (Demidov et al., 2025 ). The investigation of the crystal structure of 3-hydroxyflavones bearing a C6-electron-donating group on the A ring and a C4′-electron-withdrawing group on the B ring provides insights into the role of electron conjugation and push–pull effects (Pivovarenko & Klymchenko, 2024; Doroshenko et al., 2019 , 2026 ) on the structure, optical properties and supramolecular interactions.

2. Structural commentary

The molecular structure of the title compound, 1, is shown in Fig. 1. The asymmetric unit contains one crystallographically independent molecule. The molecule comprises a chromenone fragment bearing hydroxy and methoxy substituents and a benzaldehyde group. The methoxy substituent at atom C15 is almost coplanar with the chromenone fragment, as indicated by the C17—O5—C15—C16 torsion angle of 3.4 (3)°.

Figure 1
The molecular structure of 1, showing the atom labeling and displacement ellipsoids drawn at the 50% probability level.

The benzaldehyde ring is rotated relative to the chromenone fragment. The interfragment torsion angle C6—C5—C8—C9 is −12.8 (3)°, indicating a slight twist between the two fragments. This orientation enables an intramolecular C6—H6⋯O3 hydrogen bond (Table 1) involving a phenyl C—H group and an oxygen atom of the chromenone moiety. The oxygen atom O3, which participates in the intramolecular C—H⋯O interaction also participates in the intramolecular resonant O3—H3⋯O4 hydrogen bond in the chromenone group (Table 1). This hydrogen bond is important as it is responsible for ESIPT in compounds of this type, as mentioned earlier in the Chemical context. Thus, the O3 atom participates in two intramolecular hydrogen bonds of different types.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O1ⁱ	0.89 (2)	2.02 (2)	2.8304 (18)	151 (2)
O3—H3⋯O4	0.89 (2)	2.20 (2)	2.6853 (18)	113.6 (19)
C6—H6⋯O3	0.93	2.20	2.834 (2)	12
Symmetry code: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

3. Supramolecular features

In the crystal, molecules of 1 are linked by O3—H3⋯O1ⁱ hydrogen bonds (Table 1, Fig. 2a), forming zigzag chains along [201] (Fig. 2b). The crystal packing is further consolidated by π–π stacking interactions between chromenone rings of molecules belonging to adjacent chains [Cg1⋯Cg3(1 − x, 1 − y, 1 − z) = 3.575 (3) Å; Cg1 and Cg3 are the centroids of the O2/C8–C12 and C11 –C16 rings, respectively]. In addition, weak C7—H7⋯C3(x, $[{3\over 2}]$ − y, − $[{1\over 2}]$ + z)(π) contacts are observed between molecules from neighboring chains [H⋯C = 2.86 (3) Å, C—H⋯C = 170.4 (2)°], which also contribute to the cohesion of the crystal packing.

Figure 2
(a) The hydrogen-bonded chains of 1. (b) The crystal packing of 1. Some hydrogen-bonded chains are highlighted in different colors.

4. Hirshfeld surface analysis and fingerprint plots

The intermolecular interactions were visualized using the CrystalExplorer21 program (Spackman et al., 2021 ). The Hirshfeld surface mapped over d_norm (Spackman & Jayatilaka, 2009 ) is shown in Fig. 3. The strongest contacts, which are visualized on the Hirshfeld surface as the dark-red spots, correspond to the intermolecular O—H⋯O hydrogen bond between molecules. Lighter red spots correspond to weaker O⋯H/H⋯O interactions, such as C—H⋯O. The majority of the intermolecular interactions of 1 are weak, which results in the blue color of the Hirshfeld surface.

Figure 3
Three-dimensional Hirshfeld surface of title compound mapped over d_norm.

For further exploration of the intermolecular interactions, two-dimensional fingerprint plots (McKinnon et al., 2007 ) were generated as shown in Fig. 4. The H⋯H and O⋯H/H⋯O interactions, with contributions of 34.2% and 27.6%, respectively, have the greatest impact on the crystal packing in the solid state. The C⋯H/H⋯C interactions with 20.4%, C⋯O/O⋯C with 9.3%, C⋯C with 7.3% or O⋯O with 1.1% are less impactful in comparison.

Figure 4
Two-dimensional fingerprint plots for the title compound showing (a) all interactions, and (b)–(g) delineated into contributions from other contacts [d_e and d_i represent the distances from a point on the Hirshfeld surface to the nearest atoms outside (external) and inside (internal) the surface, respectively].

5. Database survey

A search of the Cambridge Structural Database (CSD, Version 6.00, updated March 2025; Groom et al., 2016 ) found 74 structures containing 3-hydroxyflavone. Of these, we would like to highlight 13 hits that are similar to title compound. These hits include the parent 3-hydroxyflavone itself and its derivatives (refcodes DUMFAS, DUMFEW, DUMFIA; Etter et al., 1986). The C4′-fluoro (WACTUR; Wera et al., 2010 ), C4′-hydroxy (IJUCAS; Wera et al., 2011a), and C4′-methoxy (IKAHIM; Wera et al., 2011b; IKAHIM01; Demidov et al., 2025) derivatives have been reported. The C4′-tert-butyl 3-hydroxyflavone has been reported (OHELE; Narita et al., 2015). Polymorphs of C4′-(dimethylamino) and C4′-(diethylamino) 3-hydroxyflavone has been found (BANJEN, BANJEN01, CEZDOC, CEZDOC; Hino et al., 2011 , 2013 ). 3-Hydroxyflavones with C2′-methoxy (LIGZIK01,; Shoja & Sullivan, 1999), C2′,C3-dimethoxy (PUWCUI; Koh, 2020), C3′-benzoxy (AMEBAZ, AMORUT; Demidov et al., 2025), and C7-methoxy (NUZPUT; Shoja et al., 1998) groups have been reported.

6. Synthesis and crystallization

The compound was synthesized by a modified procedure reported earlier (Demidov et al., 2025). All chemicals were purchased from commercial suppliers and used without further purification (Sigma-Aldrich, Enamine Ltd).

Hydroxy-5-methoxy-acetophenone (1.66 g, 10 mmol) and terephthalaldehyde diethyl-acetal (2.08 g, 10 mmol) were dissolved in ethanol (40 mL). Potassium hydroxide (3.36 g, 60 mmol) was added to the solution under stirring at room temperature. The reaction mixture was stirred for 24 h and conversion was monitored by TLC. After completion of the reaction hydrogen peroxide (30% H₂O₂, 3.4 mL, 30 mmol) was added dropwise to the reaction mixture, which was then placed in the ultrasound bath at room temperature for 10 minutes. After that the mixture was cooled to 273 K and acidified with 10% hydrochloric acid to reach a pH of 3 and stirred for additional 10 minutes. The resulting precipitate was filtered off and washed thoroughly with water and hexane. The crude product was recrystallized twice from i-PrOH–DMF (45:1) mixture. Yield 1.35 g (46%), yellow crystalline material, m.p. 472.5–473 K. Elemental analysis calculated for C₁₇H₁₂O_5: C, 68.92; H, 4.08. Found: C, 68.78; H, 4.15.

¹H NMR and ¹³C NMR spectra were recorded on Bruker Avance DRX 500 spectrometer at a resonance frequency of 500 and 126 MHz in DMSO-d₆. Chemical shifts are reported in the δ scale (ppm). Mass spectra were recorded on an Agilent 1100 high-performance liquid chromatograph (HPLC) equipped with a diode matrix and an Agilent LC/MSD SL mass-selective detector, a SUPELCO Ascentis Express C18 chromatographic column 2.7 µm 4.6 mm x 15 cm.

¹H NMR spectrum, δ, ppm: 10.03 (s, 1H), 9.91 (br. s, 1H), 8.36 (d, J = 8.0 Hz, 2H), 8.01 (d, J = 8.1 Hz, 2H), 7.67 (d, J = 9.7 Hz, 1H), 7.40–7.24 (m, 2H), 3.84 (s, 3H) (see Fig. S1 top).

¹³C NMR spectrum, δ, ppm: 193.1, 173.2, 156.5, 150.1, 143.7, 140.4, 137.3, 136.6, 129.9, 128.4, 124.4, 122.2, 120.6, 104.3, 56.2 (see Figure S1 bottom).

Mass spectrum, m/z (I_rel, %): 297.0 [M + H]+(100) (see Fig. S2).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were placed in calculated positions and refined by riding model with U_iso(H) = nU_eq of the carrier atom (n = 1.5 for methyl groups and n = 1.2 for other hydrogen atoms).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₂O₅
M_r	296.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.9231 (10), 18.3524 (18), 7.5479 (8)
β (°)	103.118 (3)
V (Å³)	1338.7 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.652, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	23026, 3062, 2019
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.125, 1.04
No. of reflections	3062
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.21
Computer programs: APEX2 and SAINT (Bruker, 2014 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2019/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2543411

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026003476/zn2047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026003476/zn2047Isup2.hkl

Figure S1.1H NMR (top) and 13C NMR (bottom) spectra of 1. DOI: https://doi.org/10.1107/S2056989026003476/zn2047sup3.png

Figure S2. Mass spectrum of 1. DOI: https://doi.org/10.1107/S2056989026003476/zn2047sup4.png

Supporting information file. DOI: https://doi.org/10.1107/S2056989026003476/zn2047Isup5.cml

checkCIF report

Computing details top

4-(3-Hydroxy-6-methoxy-4-oxo-4H-chromen-2-yl)benzaldehyde top

Crystal data top

C₁₇H₁₂O₅	F(000) = 616
M_r = 296.27	D_x = 1.470 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.9231 (10) Å	Cell parameters from 3272 reflections
b = 18.3524 (18) Å	θ = 2.2–24.7°
c = 7.5479 (8) Å	µ = 0.11 mm⁻¹
β = 103.118 (3)°	T = 296 K
V = 1338.7 (2) Å³	Block, yellow
Z = 4	0.3 × 0.2 × 0.1 mm

Data collection top

Bruker APEXII CCD diffractometer	2019 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
φ and ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −12→12
T_min = 0.652, T_max = 0.746	k = −23→23
23026 measured reflections	l = −9→9
3062 independent reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.125	w = 1/[σ²(F_o²) + (0.0524P)² + 0.2246P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
3062 reflections	Δρ_max = 0.23 e Å⁻³
203 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints

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. Using Olex2 (Dolomanov et al., 2009), the structure was solved with the SHELXT (Sheldrick, 2018) structure solution program using Intrinsic Phasing and refined with the SHELXL (Sheldrick, 2015) refinement package. Full-matrix least-squares refinement against F² in anisotropic approximation was used for non-hydrogen atoms.

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

	x	y	z	U_iso*/U_eq
O1	1.29775 (13)	0.69700 (7)	0.9257 (2)	0.0517 (4)
O2	0.64574 (11)	0.53802 (6)	0.76175 (16)	0.0363 (3)
O3	0.52689 (14)	0.70937 (7)	0.5462 (2)	0.0507 (4)
H3	0.440 (3)	0.7237 (13)	0.506 (3)	0.076*
O4	0.28735 (13)	0.63680 (7)	0.5116 (2)	0.0481 (4)
O5	0.17061 (13)	0.38516 (7)	0.75935 (19)	0.0459 (4)
C1	1.20045 (19)	0.71828 (10)	0.8100 (3)	0.0397 (5)
H1	1.215242	0.757103	0.737517	0.048*
C2	1.06098 (18)	0.68715 (9)	0.7761 (2)	0.0338 (4)
C3	1.03239 (18)	0.62416 (10)	0.8636 (3)	0.0374 (4)
H3A	1.103690	0.599247	0.941261	0.045*
C4	0.89871 (18)	0.59871 (10)	0.8353 (2)	0.0375 (4)
H4	0.880862	0.556435	0.893953	0.045*
C5	0.78883 (17)	0.63530 (9)	0.7197 (2)	0.0327 (4)
C6	0.81938 (19)	0.69798 (10)	0.6320 (3)	0.0402 (5)
H6	0.748651	0.723149	0.553968	0.048*
C7	0.95327 (18)	0.72287 (10)	0.6599 (3)	0.0380 (4)
H7	0.971821	0.764552	0.599509	0.046*
C8	0.64731 (17)	0.60722 (9)	0.6925 (2)	0.0331 (4)
C9	0.52761 (18)	0.64075 (9)	0.6130 (2)	0.0353 (4)
C10	0.39395 (18)	0.60553 (10)	0.5922 (2)	0.0352 (4)
C11	0.39709 (17)	0.53381 (9)	0.6732 (2)	0.0312 (4)
C12	0.52311 (17)	0.50293 (10)	0.7537 (2)	0.0326 (4)
C13	0.53046 (19)	0.43401 (10)	0.8322 (2)	0.0392 (4)
H13	0.615784	0.413493	0.885235	0.047*
C14	0.41102 (19)	0.39688 (10)	0.8306 (3)	0.0404 (5)
H14	0.415206	0.350797	0.882787	0.048*
C15	0.28218 (18)	0.42748 (10)	0.7510 (2)	0.0354 (4)
C16	0.27491 (18)	0.49510 (10)	0.6721 (2)	0.0361 (4)
H16	0.189425	0.515213	0.618100	0.043*
C17	0.03785 (19)	0.41217 (11)	0.6707 (3)	0.0479 (5)
H17A	0.035499	0.420573	0.544548	0.072*
H17B	0.020241	0.457065	0.726766	0.072*
H17C	−0.031685	0.377089	0.681216	0.072*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0366 (8)	0.0462 (9)	0.0653 (10)	−0.0042 (6)	−0.0031 (7)	0.0009 (7)
O2	0.0305 (7)	0.0323 (7)	0.0453 (8)	0.0010 (5)	0.0071 (5)	0.0060 (6)
O3	0.0325 (7)	0.0322 (8)	0.0835 (11)	0.0029 (6)	0.0051 (7)	0.0152 (7)
O4	0.0315 (7)	0.0401 (8)	0.0685 (10)	0.0041 (6)	0.0027 (6)	0.0121 (7)
O5	0.0385 (8)	0.0413 (8)	0.0565 (9)	−0.0074 (6)	0.0077 (6)	0.0086 (6)
C1	0.0383 (10)	0.0371 (11)	0.0443 (12)	−0.0015 (8)	0.0103 (8)	−0.0043 (8)
C2	0.0337 (10)	0.0303 (10)	0.0380 (10)	−0.0001 (8)	0.0097 (7)	−0.0062 (8)
C3	0.0322 (10)	0.0352 (10)	0.0418 (11)	0.0037 (8)	0.0024 (8)	0.0009 (8)
C4	0.0376 (10)	0.0316 (10)	0.0430 (11)	0.0017 (8)	0.0087 (8)	0.0025 (8)
C5	0.0305 (9)	0.0316 (10)	0.0359 (10)	0.0038 (7)	0.0073 (7)	−0.0033 (7)
C6	0.0339 (10)	0.0374 (11)	0.0486 (12)	0.0040 (8)	0.0081 (8)	0.0085 (9)
C7	0.0370 (10)	0.0331 (10)	0.0443 (11)	−0.0001 (8)	0.0105 (8)	0.0046 (8)
C8	0.0335 (10)	0.0289 (10)	0.0372 (10)	0.0016 (7)	0.0087 (7)	0.0007 (7)
C9	0.0354 (10)	0.0270 (10)	0.0431 (11)	0.0010 (8)	0.0082 (8)	0.0018 (8)
C10	0.0310 (10)	0.0341 (10)	0.0399 (11)	0.0024 (8)	0.0066 (8)	−0.0005 (8)
C11	0.0307 (9)	0.0294 (9)	0.0338 (10)	0.0011 (7)	0.0081 (7)	−0.0009 (7)
C12	0.0323 (9)	0.0313 (10)	0.0342 (10)	0.0004 (7)	0.0075 (7)	−0.0009 (7)
C13	0.0379 (10)	0.0360 (11)	0.0415 (11)	0.0049 (8)	0.0044 (8)	0.0062 (8)
C14	0.0436 (11)	0.0333 (10)	0.0427 (11)	−0.0001 (8)	0.0066 (8)	0.0068 (8)
C15	0.0372 (10)	0.0345 (10)	0.0352 (10)	−0.0051 (8)	0.0096 (8)	−0.0023 (8)
C16	0.0329 (10)	0.0352 (10)	0.0398 (11)	0.0012 (8)	0.0071 (7)	−0.0003 (8)
C17	0.0358 (11)	0.0466 (12)	0.0604 (14)	−0.0061 (9)	0.0093 (9)	0.0029 (10)

Geometric parameters (Å, º) top

O1—C1	1.210 (2)	C6—H6	0.9300
O2—C8	1.375 (2)	C6—C7	1.375 (2)
O2—C12	1.366 (2)	C7—H7	0.9300
O3—H3	0.89 (2)	C8—C9	1.351 (2)
O3—C9	1.356 (2)	C9—C10	1.451 (2)
O4—C10	1.2354 (19)	C10—C11	1.449 (2)
O5—C15	1.366 (2)	C11—C12	1.382 (2)
O5—C17	1.424 (2)	C11—C16	1.404 (2)
C1—H1	0.9300	C12—C13	1.392 (2)
C1—C2	1.465 (2)	C13—H13	0.9300
C2—C3	1.392 (2)	C13—C14	1.365 (2)
C2—C7	1.384 (2)	C14—H14	0.9300
C3—H3A	0.9300	C14—C15	1.401 (2)
C3—C4	1.377 (2)	C15—C16	1.371 (3)
C4—H4	0.9300	C16—H16	0.9300
C4—C5	1.403 (2)	C17—H17A	0.9600
C5—C6	1.395 (3)	C17—H17B	0.9600
C5—C8	1.466 (2)	C17—H17C	0.9600

C12—O2—C8	120.37 (13)	C8—C9—C10	122.34 (16)
C9—O3—H3	108.8 (16)	O4—C10—C9	120.39 (16)
C15—O5—C17	116.97 (14)	O4—C10—C11	124.31 (16)
O1—C1—H1	117.7	C11—C10—C9	115.29 (15)
O1—C1—C2	124.56 (18)	C12—C11—C10	119.27 (15)
C2—C1—H1	117.7	C12—C11—C16	119.29 (16)
C3—C2—C1	121.82 (17)	C16—C11—C10	121.44 (15)
C7—C2—C1	119.26 (17)	O2—C12—C11	122.29 (15)
C7—C2—C3	118.86 (16)	O2—C12—C13	116.72 (15)
C2—C3—H3A	120.0	C11—C12—C13	120.99 (16)
C4—C3—C2	120.07 (17)	C12—C13—H13	120.4
C4—C3—H3A	120.0	C14—C13—C12	119.23 (17)
C3—C4—H4	119.3	C14—C13—H13	120.4
C3—C4—C5	121.30 (17)	C13—C14—H14	119.7
C5—C4—H4	119.3	C13—C14—C15	120.67 (17)
C4—C5—C8	120.21 (16)	C15—C14—H14	119.7
C6—C5—C4	117.91 (16)	O5—C15—C14	115.02 (16)
C6—C5—C8	121.88 (16)	O5—C15—C16	124.85 (16)
C5—C6—H6	119.7	C16—C15—C14	120.13 (17)
C7—C6—C5	120.51 (17)	C11—C16—H16	120.2
C7—C6—H6	119.7	C15—C16—C11	119.69 (17)
C2—C7—H7	119.3	C15—C16—H16	120.2
C6—C7—C2	121.33 (17)	O5—C17—H17A	109.5
C6—C7—H7	119.3	O5—C17—H17B	109.5
O2—C8—C5	111.39 (14)	O5—C17—H17C	109.5
C9—C8—O2	120.31 (15)	H17A—C17—H17B	109.5
C9—C8—C5	128.29 (16)	H17A—C17—H17C	109.5
O3—C9—C10	116.47 (15)	H17B—C17—H17C	109.5
C8—C9—O3	121.19 (16)

O1—C1—C2—C3	−7.2 (3)	C7—C2—C3—C4	−0.6 (3)
O1—C1—C2—C7	170.05 (18)	C8—O2—C12—C11	1.6 (2)
O2—C8—C9—O3	179.08 (16)	C8—O2—C12—C13	−177.93 (16)
O2—C8—C9—C10	−1.7 (3)	C8—C5—C6—C7	−179.85 (17)
O2—C12—C13—C14	179.03 (16)	C8—C9—C10—O4	−176.81 (18)
O3—C9—C10—O4	2.4 (3)	C8—C9—C10—C11	3.9 (3)
O3—C9—C10—C11	−176.89 (16)	C9—C10—C11—C12	−3.3 (2)
O4—C10—C11—C12	177.41 (18)	C9—C10—C11—C16	176.49 (16)
O4—C10—C11—C16	−2.8 (3)	C10—C11—C12—O2	0.7 (3)
O5—C15—C16—C11	179.50 (15)	C10—C11—C12—C13	−179.71 (17)
C1—C2—C3—C4	176.63 (16)	C10—C11—C16—C15	−179.66 (17)
C1—C2—C7—C6	−176.28 (17)	C11—C12—C13—C14	−0.5 (3)
C2—C3—C4—C5	−0.3 (3)	C12—O2—C8—C5	178.44 (14)
C3—C2—C7—C6	1.0 (3)	C12—O2—C8—C9	−1.1 (2)
C3—C4—C5—C6	0.8 (3)	C12—C11—C16—C15	0.1 (3)
C3—C4—C5—C8	−179.71 (16)	C12—C13—C14—C15	0.0 (3)
C4—C5—C6—C7	−0.4 (3)	C13—C14—C15—O5	−179.54 (16)
C4—C5—C8—O2	−11.8 (2)	C13—C14—C15—C16	0.6 (3)
C4—C5—C8—C9	167.75 (18)	C14—C15—C16—C11	−0.7 (3)
C5—C6—C7—C2	−0.5 (3)	C16—C11—C12—O2	−179.07 (15)
C5—C8—C9—O3	−0.4 (3)	C16—C11—C12—C13	0.5 (3)
C5—C8—C9—C10	178.76 (16)	C17—O5—C15—C14	−176.38 (16)
C6—C5—C8—O2	167.64 (16)	C17—O5—C15—C16	3.4 (3)
C6—C5—C8—C9	−12.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1ⁱ	0.89 (2)	2.02 (2)	2.8304 (18)	151 (2)
O3—H3···O4	0.89 (2)	2.20 (2)	2.6853 (18)	113.6 (19)
C6—H6···O3	0.93	2.20	2.834 (2)	12

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

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