(E)-1-(2-Hy­droxy-4,6-di­meth­oxy­phen­yl)-3-(naph­thalen-1-yl)prop-2-en-1-one

Koh, D.

doi:10.1107/S2414314622009324

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 9| September 2022| x220932

https://doi.org/10.1107/S2414314622009324

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(E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one

Dongsoo Koh ^a ^*

^aDepartment of Applied Chemistry, Dongduk Women's University, Seoul, 02748, Republic of Korea
^*Correspondence e-mail: dskoh@dongduk.ac.kr

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 19 September 2022; accepted 22 September 2022; online 27 September 2022)

In the title compound, C₂₁H₁₈O₄, the relative conformation of the C=C and C=O double bonds in the central enone group is s-cisoid; there is a trans configuration about the C=C bond. The dihedral angle formed by the naphthalene ring system and the benzene ring is 16.80 (2)°. The methoxy groups at the ortho and para positions of the benzene ring are tilted to the ring by 169.8 (1) and 174.5 (1)°, respectively. The hydroxy group in the benzene ring participates in an intramolecular O—H⋯O hydrogen bond. In the crystal, C—H⋯O interactions link molecules into linear chains along the a-axis direction.

Keywords: crystal structure; chalcone; O—H⋯O hydrogen bond; C—H⋯O interactions.

CCDC reference: 2208753

Structure description

Reactive oxygen species (ROS) damage DNA, RNA, and proteins when present in excess. There is growing evidence that flavonoids can suppress carcinogenesis by inhibiting ROS levels (Rodríguez-García et al., 2019 ). Surprisingly, flavonoids can also induce excessive oxidative stress, leading to cancer cell death (Slika et al., 2022 ). Flavones (Hostetler et al., 2017 ), aurones (Sui et al., 2021 ), and chalcones (Elkanzi et al., 2022 ), which belong to the sub-group of flavonoids, have in common an α,β-unsaturated carbonyl group in the molecule. The α,β-unsaturated carbonyl group reacts with the thiol group of glutathione (GSH) as a Michael acceptor to reduce the intracellular GSH concentration (Adams et al., 2012 ). Since cancer cells have a higher ROS concentration than normal cells (Kumari et al., 2018 ), α,β-unsaturated carbonyl groups rapidly increase ROS levels due to decreased GSH, thereby killing cancer cells (Raj et al., 2011 ). As an extension of the search for ROS-generating compounds in cancer cells (Shin et al., 2022 ; Lee et al., 2016 ), the title chalcone compound was synthesized.

The molecular structure of the title compound is shown in Fig. 1. In the central α,β-unsaturated carbonyl group, the carbonyl O1=C1 and C2=C3 double bonds are twisted at an angle of −22.9 (2)° for the C3—C2—C1—O1 torsion angle. A trans-configuration is noted for the C2=C3 double bond, which has a torsion angle of −178.3 (1)° for C1—C2—C3—C4. The methoxy group at the para position (C-17) of the benzene ring is nearly coplanar with the ring [C18—C17—O3—C20 = 174.5 (1)°], while the other methoxy group at the ortho position (C-19) is more twisted out of the ring [C14—C19—O4—C21 = 169.8 (1)°]. The naphthalene ring system (C4–C13; r.m.s. deviation of 0.003 Å) is tilted at an angle of 16.80 (2)° with respect to the benzene ring (C14–C19; r.m.s. deviation of 0.011 Å). The hydroxy group attached to the benzene ring is involved in an intramolecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯O interactions link the molecules into linear chains propagating along the a-axis direction (Fig. 2, Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O1	0.94 (2)	1.60 (2)	2.4869 (12)	155.5 (18)
C21—H21C⋯O2ⁱ	0.98	2.58	3.3393 (17)	135
Symmetry code: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Figure 1
The molecular structure of the title compound, showing the atom-labeling scheme and displacement ellipsoids drawn at the 50% probability level. The dashed bond represents the intramolecular O—H⋯O hydrogen bond.

Figure 2
Part of the crystal structure of the title compound with weak intermolecular C—H⋯O interactions shown as green dashed lines.

Synthesis and crystallization

1-(2-Hydroxy-4,6-dimethoxyphenyl)ethanone (196 mg, 1 mmol) and 1-naphthaldehyde (156 mg, 1 mmol) were dissolved in ethanol (25 ml) and the temperature was cooled to around 276–277 K in an ice bath. To the cooled reaction mixture were added 1.0 ml of 40% aqueous KOH solution, and the reaction mixture was stirred at room temperature for 20 h. This mixture was poured into iced water (40 ml) and acidified with 6 N HCl solution. The mixture was extracted with ethyl acetate (2 × 30 ml) and the combined organic layers were dried over MgSO₄. Filtration and evaporation of the filtrate gave a residue which was purified by flash chromatography to give the title compound (260 mg, 78%). Recrystallization in ethanol gave the crystals used in this X-ray diffraction study.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₁₈O₄
M_r	334.35
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	147
a, b, c (Å)	15.8594 (7), 5.0437 (2), 40.6908 (17)
β (°)	90.507 (2)
V (Å³)	3254.7 (2)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.77
Crystal size (mm)	0.65 × 0.11 × 0.03

Data collection
Diffractometer	Bruker Kappa APEX DUO CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2012 )
T_min, T_max	0.655, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	10590, 2743, 2555
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.098, 1.03
No. of reflections	2743
No. of parameters	232
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.22
Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXS and SHELXTL (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2208753

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622009324/tk4085sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622009324/tk4085Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622009324/tk4085Isup3.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).

(E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one top

Crystal data top

C₂₁H₁₈O₄	F(000) = 1408
M_r = 334.35	D_x = 1.365 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 6156 reflections
a = 15.8594 (7) Å	θ = 6.5–66.5°
b = 5.0437 (2) Å	µ = 0.77 mm⁻¹
c = 40.6908 (17) Å	T = 147 K
β = 90.507 (2)°	Needle, yellow
V = 3254.7 (2) Å³	0.65 × 0.11 × 0.03 mm
Z = 8

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	2743 independent reflections
Radiation source: Bruker ImuS	2555 reflections with I > 2σ(I)
Multi-layer optics monochromator	R_int = 0.027
φ and ω scans	θ_max = 66.5°, θ_min = 6.5°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −18→18
T_min = 0.655, T_max = 0.753	k = −5→1
10590 measured reflections	l = −48→47

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.098	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0514P)² + 2.058P] where P = (F_o² + 2F_c²)/3
2743 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.22 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
O1	0.83835 (5)	0.92735 (19)	0.40390 (2)	0.0331 (2)
O2	0.82944 (5)	1.26680 (18)	0.44807 (2)	0.0286 (2)
O3	0.56231 (5)	1.62372 (18)	0.47470 (2)	0.0289 (2)
O4	0.57849 (5)	0.93109 (17)	0.39751 (2)	0.0277 (2)
C1	0.75984 (8)	0.9014 (2)	0.40286 (3)	0.0233 (3)
C2	0.72497 (8)	0.6836 (3)	0.38301 (3)	0.0278 (3)
H2A	0.6702	0.6195	0.3880	0.033*
C3	0.76623 (8)	0.5731 (2)	0.35859 (3)	0.0267 (3)
H3A	0.8215	0.6365	0.3543	0.032*
C4	0.73370 (8)	0.3599 (2)	0.33742 (3)	0.0239 (3)
C5	0.64822 (8)	0.3106 (3)	0.33554 (3)	0.0284 (3)
H5A	0.6109	0.4154	0.3483	0.034*
C6	0.61469 (9)	0.1099 (3)	0.31536 (3)	0.0309 (3)
H6A	0.5555	0.0802	0.3147	0.037*
C7	0.66664 (9)	−0.0425 (3)	0.29668 (3)	0.0294 (3)
H7A	0.6435	−0.1779	0.2831	0.035*
C8	0.75456 (8)	−0.0002 (2)	0.29737 (3)	0.0250 (3)
C9	0.80929 (9)	−0.1570 (3)	0.27802 (3)	0.0319 (3)
H9A	0.7863	−0.2930	0.2645	0.038*
C10	0.89410 (10)	−0.1162 (3)	0.27848 (3)	0.0371 (3)
H10A	0.9298	−0.2226	0.2653	0.045*
C11	0.92890 (9)	0.0833 (3)	0.29851 (4)	0.0363 (3)
H11A	0.9882	0.1111	0.2988	0.044*
C12	0.87801 (8)	0.2379 (3)	0.31759 (3)	0.0294 (3)
H12A	0.9026	0.3716	0.3310	0.035*
C13	0.78924 (8)	0.2026 (2)	0.31770 (3)	0.0232 (3)
C14	0.70640 (8)	1.0824 (2)	0.42166 (3)	0.0212 (3)
C15	0.74516 (7)	1.2624 (2)	0.44389 (3)	0.0220 (3)
C16	0.69958 (8)	1.4415 (2)	0.46266 (3)	0.0230 (3)
H16A	0.7273	1.5536	0.4781	0.028*
C17	0.61307 (8)	1.4532 (2)	0.45848 (3)	0.0232 (3)
C18	0.57152 (8)	1.2849 (2)	0.43638 (3)	0.0240 (3)
H18A	0.5121	1.2976	0.4335	0.029*
C19	0.61656 (8)	1.1008 (2)	0.41876 (3)	0.0216 (3)
C20	0.60019 (9)	1.7843 (3)	0.49980 (3)	0.0298 (3)
H20A	0.5563	1.8845	0.5112	0.045*
H20B	0.6402	1.9079	0.4898	0.045*
H20C	0.6300	1.6705	0.5156	0.045*
C21	0.48877 (9)	0.9150 (3)	0.39821 (4)	0.0405 (4)
H21A	0.4699	0.7638	0.3849	0.061*
H21B	0.4645	1.0787	0.3893	0.061*
H21C	0.4703	0.8914	0.4209	0.061*
H2O	0.8485 (12)	1.142 (4)	0.4325 (5)	0.064 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0226 (5)	0.0357 (5)	0.0409 (5)	0.0010 (4)	0.0022 (4)	−0.0128 (4)
O2	0.0200 (5)	0.0321 (5)	0.0336 (5)	−0.0005 (4)	−0.0009 (4)	−0.0081 (4)
O3	0.0249 (5)	0.0318 (5)	0.0300 (5)	0.0043 (4)	0.0027 (4)	−0.0074 (4)
O4	0.0236 (5)	0.0297 (5)	0.0297 (5)	−0.0045 (4)	−0.0016 (4)	−0.0066 (4)
C1	0.0257 (6)	0.0215 (6)	0.0226 (6)	−0.0003 (5)	0.0024 (5)	0.0037 (5)
C2	0.0258 (7)	0.0260 (7)	0.0318 (7)	−0.0011 (5)	0.0024 (5)	−0.0035 (5)
C3	0.0247 (6)	0.0260 (7)	0.0294 (6)	0.0011 (5)	−0.0008 (5)	−0.0029 (5)
C4	0.0280 (7)	0.0229 (6)	0.0208 (6)	0.0006 (5)	−0.0006 (5)	0.0020 (5)
C5	0.0289 (7)	0.0280 (7)	0.0283 (6)	0.0008 (5)	0.0018 (5)	−0.0009 (5)
C6	0.0278 (7)	0.0334 (7)	0.0313 (7)	−0.0060 (6)	−0.0026 (5)	0.0016 (6)
C7	0.0385 (8)	0.0259 (7)	0.0238 (6)	−0.0061 (6)	−0.0059 (5)	−0.0001 (5)
C8	0.0352 (7)	0.0216 (6)	0.0182 (6)	0.0002 (5)	−0.0021 (5)	0.0035 (5)
C9	0.0446 (8)	0.0268 (7)	0.0243 (6)	0.0008 (6)	−0.0007 (6)	−0.0043 (5)
C10	0.0420 (8)	0.0352 (8)	0.0342 (7)	0.0078 (6)	0.0074 (6)	−0.0073 (6)
C11	0.0303 (7)	0.0374 (8)	0.0414 (8)	0.0035 (6)	0.0042 (6)	−0.0048 (6)
C12	0.0298 (7)	0.0275 (7)	0.0310 (7)	0.0000 (5)	−0.0001 (5)	−0.0041 (5)
C13	0.0293 (7)	0.0209 (6)	0.0194 (6)	0.0013 (5)	−0.0011 (5)	0.0030 (5)
C14	0.0236 (6)	0.0195 (6)	0.0206 (6)	−0.0016 (5)	0.0017 (5)	0.0024 (5)
C15	0.0215 (6)	0.0224 (6)	0.0219 (6)	−0.0017 (5)	0.0004 (5)	0.0040 (5)
C16	0.0257 (6)	0.0225 (6)	0.0208 (6)	−0.0020 (5)	0.0002 (5)	−0.0015 (5)
C17	0.0261 (6)	0.0220 (6)	0.0217 (6)	0.0018 (5)	0.0044 (5)	0.0019 (5)
C18	0.0200 (6)	0.0264 (7)	0.0257 (6)	−0.0005 (5)	0.0007 (5)	0.0020 (5)
C19	0.0243 (6)	0.0210 (6)	0.0195 (6)	−0.0037 (5)	0.0003 (5)	0.0026 (5)
C20	0.0331 (7)	0.0314 (7)	0.0249 (6)	0.0060 (6)	0.0009 (5)	−0.0055 (5)
C21	0.0231 (7)	0.0492 (9)	0.0490 (9)	−0.0054 (6)	−0.0050 (6)	−0.0144 (7)

Geometric parameters (Å, º) top

O1—C1	1.2523 (15)	C9—C10	1.361 (2)
O2—C15	1.3461 (15)	C9—H9A	0.9500
O2—H2O	0.94 (2)	C10—C11	1.405 (2)
O3—C17	1.3538 (15)	C10—H10A	0.9500
O3—C20	1.4316 (15)	C11—C12	1.3688 (19)
O4—C19	1.3549 (15)	C11—H11A	0.9500
O4—C21	1.4258 (16)	C12—C13	1.4190 (18)
C1—C14	1.4656 (17)	C12—H12A	0.9500
C1—C2	1.4688 (18)	C14—C15	1.4181 (17)
C2—C3	1.3182 (19)	C14—C19	1.4316 (17)
C2—H2A	0.9500	C15—C16	1.3896 (17)
C3—C4	1.4685 (18)	C16—C17	1.3823 (17)
C3—H3A	0.9500	C16—H16A	0.9500
C4—C5	1.3797 (18)	C17—C18	1.3974 (18)
C4—C13	1.4360 (17)	C18—C19	1.3769 (17)
C5—C6	1.4051 (19)	C18—H18A	0.9500
C5—H5A	0.9500	C20—H20A	0.9800
C6—C7	1.363 (2)	C20—H20B	0.9800
C6—H6A	0.9500	C20—H20C	0.9800
C7—C8	1.4105 (19)	C21—H21A	0.9800
C7—H7A	0.9500	C21—H21B	0.9800
C8—C9	1.4178 (18)	C21—H21C	0.9800
C8—C13	1.4232 (18)

C15—O2—H2O	103.2 (12)	C11—C12—C13	121.35 (12)
C17—O3—C20	117.37 (10)	C11—C12—H12A	119.3
C19—O4—C21	117.53 (10)	C13—C12—H12A	119.3
O1—C1—C14	119.78 (11)	C12—C13—C8	117.82 (11)
O1—C1—C2	117.78 (11)	C12—C13—C4	123.08 (11)
C14—C1—C2	122.42 (11)	C8—C13—C4	119.09 (11)
C3—C2—C1	122.95 (12)	C15—C14—C19	115.88 (11)
C3—C2—H2A	118.5	C15—C14—C1	118.83 (11)
C1—C2—H2A	118.5	C19—C14—C1	125.25 (11)
C2—C3—C4	125.29 (12)	O2—C15—C16	116.16 (11)
C2—C3—H3A	117.4	O2—C15—C14	121.02 (11)
C4—C3—H3A	117.4	C16—C15—C14	122.82 (11)
C5—C4—C13	118.47 (11)	C17—C16—C15	118.74 (11)
C5—C4—C3	120.29 (11)	C17—C16—H16A	120.6
C13—C4—C3	121.22 (11)	C15—C16—H16A	120.6
C4—C5—C6	121.93 (12)	O3—C17—C16	124.13 (11)
C4—C5—H5A	119.0	O3—C17—C18	114.87 (11)
C6—C5—H5A	119.0	C16—C17—C18	121.00 (11)
C7—C6—C5	120.30 (12)	C19—C18—C17	120.06 (11)
C7—C6—H6A	119.8	C19—C18—H18A	120.0
C5—C6—H6A	119.8	C17—C18—H18A	120.0
C6—C7—C8	120.41 (12)	O4—C19—C18	121.88 (11)
C6—C7—H7A	119.8	O4—C19—C14	116.69 (10)
C8—C7—H7A	119.8	C18—C19—C14	121.43 (11)
C7—C8—C9	120.98 (12)	O3—C20—H20A	109.5
C7—C8—C13	119.80 (11)	O3—C20—H20B	109.5
C9—C8—C13	119.22 (12)	H20A—C20—H20B	109.5
C10—C9—C8	121.20 (12)	O3—C20—H20C	109.5
C10—C9—H9A	119.4	H20A—C20—H20C	109.5
C8—C9—H9A	119.4	H20B—C20—H20C	109.5
C9—C10—C11	119.97 (13)	O4—C21—H21A	109.5
C9—C10—H10A	120.0	O4—C21—H21B	109.5
C11—C10—H10A	120.0	H21A—C21—H21B	109.5
C12—C11—C10	120.43 (13)	O4—C21—H21C	109.5
C12—C11—H11A	119.8	H21A—C21—H21C	109.5
C10—C11—H11A	119.8	H21B—C21—H21C	109.5

O1—C1—C2—C3	−22.91 (19)	C3—C4—C13—C8	−179.47 (11)
C14—C1—C2—C3	158.34 (12)	O1—C1—C14—C15	−7.79 (17)
C1—C2—C3—C4	−178.35 (11)	C2—C1—C14—C15	170.93 (11)
C2—C3—C4—C5	18.8 (2)	O1—C1—C14—C19	169.92 (11)
C2—C3—C4—C13	−162.71 (13)	C2—C1—C14—C19	−11.36 (18)
C13—C4—C5—C6	0.90 (18)	C19—C14—C15—O2	−178.57 (10)
C3—C4—C5—C6	179.46 (12)	C1—C14—C15—O2	−0.65 (16)
C4—C5—C6—C7	−0.4 (2)	C19—C14—C15—C16	1.93 (17)
C5—C6—C7—C8	−0.08 (19)	C1—C14—C15—C16	179.84 (11)
C6—C7—C8—C9	−179.90 (12)	O2—C15—C16—C17	177.50 (10)
C6—C7—C8—C13	0.03 (18)	C14—C15—C16—C17	−2.97 (18)
C7—C8—C9—C10	179.69 (12)	C20—O3—C17—C16	−5.82 (17)
C13—C8—C9—C10	−0.25 (19)	C20—O3—C17—C18	174.47 (10)
C8—C9—C10—C11	0.3 (2)	C15—C16—C17—O3	−178.27 (11)
C9—C10—C11—C12	−0.1 (2)	C15—C16—C17—C18	1.42 (17)
C10—C11—C12—C13	−0.2 (2)	O3—C17—C18—C19	−179.20 (10)
C11—C12—C13—C8	0.25 (19)	C16—C17—C18—C19	1.08 (18)
C11—C12—C13—C4	179.78 (12)	C21—O4—C19—C18	−11.21 (17)
C7—C8—C13—C12	−179.98 (11)	C21—O4—C19—C14	169.78 (11)
C9—C8—C13—C12	−0.05 (17)	C17—C18—C19—O4	178.90 (10)
C7—C8—C13—C4	0.46 (17)	C17—C18—C19—C14	−2.14 (18)
C9—C8—C13—C4	−179.60 (11)	C15—C14—C19—O4	179.68 (10)
C5—C4—C13—C12	179.56 (11)	C1—C14—C19—O4	1.91 (17)
C3—C4—C13—C12	1.01 (18)	C15—C14—C19—C18	0.67 (16)
C5—C4—C13—C8	−0.91 (17)	C1—C14—C19—C18	−177.10 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.94 (2)	1.60 (2)	2.4869 (12)	155.5 (18)
C21—H21C···O2ⁱ	0.98	2.58	3.3393 (17)	135

Symmetry code: (i) x−1/2, y−1/2, z.

Acknowledgements

This work was supported by a Dongduk Women's University grant.

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