3-[4-(Benz­yloxy)phen­yl]-1-(2-fur­yl)-3-hydroxy­prop-2-en-1-one

Zheng, C.-Y.; Wang, D.-J.; Fan, L.

doi:10.1107/S1600536808036659

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2326

doi:10.1107/S1600536808036659

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3-[4-(Benzyloxy)phenyl]-1-(2-furyl)-3-hydroxyprop-2-en-1-one

Chun-Yang Zheng,^a ^* Dun-Jia Wang ^b and Ling Fan ^b

^aHubei Key Laboratory of Bioanalytical Techniques, Hubei Normal University, Huangshi 435002, People's Republic of China, and ^bCollege of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, People's Republic of China
^*Correspondence e-mail: zcy800204@163.com

(Received 3 November 2008; accepted 7 November 2008; online 13 November 2008)

In the crystal structure of the title compound, C₂₀H₁₆O₄, which is in the enol form, the central benzene ring makes dihedral angles of 63.42 (9) and 5.19 (10)° with the phenyl and furan rings, respectively. There is a short strong intramolecular O—H⋯O hydrogen bond.

Related literature

For hydrogen bonds in 1,3-diketones, see: Bertolasi et al. (1991 ); Gilli et al. (2004 ); Vila et al. (1991 ). For 1,3-diketones as ligands, see: Baskar & Roesky (2005 ); Bassett et al. (2004 ); Jang et al. (2006 ); Soldatov et al. (2003 ).

Experimental

Crystal data

C₂₀H₁₆O₄
M_r = 320.33
Triclinic, $[P \overline 1]$
a = 5.8927 (6) Å
b = 11.3365 (11) Å
c = 13.3039 (13) Å
α = 112.111 (3)°
β = 96.687 (3)°
γ = 98.638 (3)°
V = 799.39 (14) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 (2) K
0.32 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.978, T_max = 0.983
6611 measured reflections
3439 independent reflections
2268 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.147
S = 0.95
3439 reflections
220 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3	1.15 (3)	1.38 (3)	2.5030 (16)	162 (2)

Data collection: SMART (Bruker, 1997 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808036659/is2357sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808036659/is2357Isup2.hkl

checkCIF report

Comment top

1,3-Diketones in their enolic tautomeric forms have been extensively studied owing to their ability to form strong intermolecular or intramolecular hydrogen bonds (Vila et al., 1991; Bertolasi et al., 1991; Gilli et al., 2004). They are among the most studied ligands in the chemistry of metal complexes and used widely in the chemistry of metallocomplexes (Baskar & Roesky, 2005; Bassett et al., 2004; Jang et al., 2006; Soldatov et al., 2003).

The crystal structure of the title compound, (I), is in the enol form stabilized by an intramolecular hydrogen bond (Fig. 1). The distances of O2—H2 and O3···H2 are 1.15 (3) and 1.38 (3) Å, respectively. The central benzene ring (C8—C13) makes dihedral angles of 63.42 and 5.19° with two aromatic rings (C1—C6) and (C17—O4), respectively. The crystal packing is stabilized by van der Waals forces.

Related literature top

For hydrogen bonds in 1,3-diketones, see: Bertolasi et al. (1991); Gilli et al. (2004); Vila et al. (1991). For 1,3-diketones as ligands, see: Baskar & Roesky (2005); Bassett et al. (2004); Jang et al. (2006); Soldatov et al. (2003).

Experimental top

1-[4-(Benzyloxy)phenyl]ethanone (2.26 g, 0.01 mol), methyl furan-2-carboxylate (1.26 g, 0.01 mol), NaNH₂ (0.78 g, 0.02 mol) and dry ether (60 ml) were placed into round bottom flask. The mixture was stirred for 6 h at room temperature under a blanket of nitrogen, acidified with dilute hydrochloric acid, and stirring was continued until all solids dissolved. The ether layer was separated and washed with saturated NaHCO₃ solution, dried over anhydrous Na₂SO₄ and was removed by evaporation. The residual solid was recrystallized from an ethanol solution to give the title compound (I) (yield 1.75 g, 54.7%; m.p. 403 K). Crystals suitable for X-ray diffraction were grown by slow evaporation of a CH₂Cl₂—EtOH (1:4) solution at room temperature.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. View of (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. The dashed line indicates an intramolecular hydrogen bond.

3-[4-(Benzyloxy)phenyl]-1-(2-furyl)-3-hydroxyprop-2-en-1-one top

Crystal data top

C₂₀H₁₆O₄	Z = 2
M_r = 320.33	F(000) = 336
Triclinic, P1	D_x = 1.331 Mg m⁻³
Hall symbol: -P 1	Melting point: 403 K
a = 5.8927 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.3365 (11) Å	Cell parameters from 1997 reflections
c = 13.3039 (13) Å	θ = 3.1–26.1°
α = 112.111 (3)°	µ = 0.09 mm⁻¹
β = 96.687 (3)°	T = 298 K
γ = 98.638 (3)°	Block, yellow
V = 799.39 (14) Å³	0.32 × 0.20 × 0.12 mm

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3439 independent reflections
Radiation source: fine-focus sealed tube	2268 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
T_min = 0.978, T_max = 0.983	k = −14→14
6611 measured reflections	l = −16→16

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	w = 1/[σ²(F_o²) + (0.0676P)²] where P = (F_o² + 2F_c²)/3
3439 reflections	(Δ/σ)_max < 0.001
220 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₂₀H₁₆O₄	γ = 98.638 (3)°
M_r = 320.33	V = 799.39 (14) Å³
Triclinic, P1	Z = 2
a = 5.8927 (6) Å	Mo Kα radiation
b = 11.3365 (11) Å	µ = 0.09 mm⁻¹
c = 13.3039 (13) Å	T = 298 K
α = 112.111 (3)°	0.32 × 0.20 × 0.12 mm
β = 96.687 (3)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	3439 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2268 reflections with I > 2σ(I)
T_min = 0.978, T_max = 0.983	R_int = 0.078
6611 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	0 restraints
wR(F²) = 0.147	H atoms treated by a mixture of independent and constrained refinement
S = 0.95	Δρ_max = 0.18 e Å⁻³
3439 reflections	Δρ_min = −0.29 e Å⁻³
220 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	−0.1919 (3)	0.94140 (17)	−0.21175 (14)	0.0561 (4)
H1	−0.2852	0.9490	−0.1588	0.067*
C2	−0.2151 (3)	1.01001 (18)	−0.27760 (15)	0.0624 (5)
H2	−0.3229	1.0636	−0.2686	0.075*
C3	−0.0791 (3)	0.99904 (18)	−0.35624 (13)	0.0628 (5)
H3	−0.0943	1.0449	−0.4008	0.075*
C4	0.0791 (4)	0.9200 (2)	−0.36863 (14)	0.0707 (5)
H4	0.1716	0.9124	−0.4219	0.085*
C5	0.1021 (3)	0.85205 (18)	−0.30303 (14)	0.0625 (5)
H5	0.2100	0.7986	−0.3124	0.075*
C6	−0.0332 (3)	0.86224 (15)	−0.22321 (12)	0.0470 (4)
C7	−0.0042 (3)	0.78860 (17)	−0.15223 (14)	0.0543 (4)
H7A	−0.1266	0.7946	−0.1088	0.065*
H7B	−0.0133	0.6975	−0.1976	0.065*
C8	0.2985 (3)	0.78337 (14)	−0.01798 (12)	0.0437 (4)
C9	0.1650 (3)	0.67956 (17)	−0.00705 (15)	0.0572 (5)
H9	0.0099	0.6479	−0.0432	0.069*
C10	0.2624 (3)	0.62314 (17)	0.05756 (14)	0.0566 (5)
H10	0.1708	0.5530	0.0641	0.068*
C11	0.4923 (3)	0.66708 (14)	0.11326 (12)	0.0430 (4)
C12	0.6215 (3)	0.77425 (15)	0.10371 (12)	0.0487 (4)
H12	0.7755	0.8073	0.1413	0.058*
C13	0.5265 (3)	0.83230 (15)	0.04000 (13)	0.0493 (4)
H13	0.6155	0.9047	0.0357	0.059*
C14	0.5877 (3)	0.60034 (15)	0.17882 (12)	0.0459 (4)
C15	0.8145 (3)	0.63971 (16)	0.23933 (13)	0.0493 (4)
H15	0.9149	0.7099	0.2370	0.059*
C16	0.8939 (3)	0.57587 (17)	0.30329 (13)	0.0523 (4)
C17	1.1263 (3)	0.62181 (18)	0.37217 (13)	0.0561 (4)
C18	1.2389 (4)	0.5838 (2)	0.44496 (16)	0.0779 (6)
H18	1.1821	0.5149	0.4632	0.094*
C19	1.4595 (4)	0.6689 (3)	0.48793 (17)	0.0878 (7)
H19	1.5767	0.6671	0.5402	0.105*
C20	1.4681 (4)	0.7517 (2)	0.43989 (17)	0.0821 (7)
H20	1.5957	0.8185	0.4537	0.099*
O1	0.22079 (19)	0.84506 (10)	−0.08083 (9)	0.0549 (3)
O2	0.4480 (2)	0.49997 (11)	0.17879 (10)	0.0593 (3)
O3	0.7661 (2)	0.47547 (13)	0.30691 (11)	0.0682 (4)
O4	1.2673 (2)	0.72692 (13)	0.36792 (9)	0.0661 (4)
H2A	0.573 (4)	0.473 (2)	0.2360 (18)	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0612 (10)	0.0584 (11)	0.0545 (10)	0.0197 (8)	0.0132 (8)	0.0256 (9)
C2	0.0691 (11)	0.0551 (11)	0.0649 (11)	0.0249 (9)	0.0015 (9)	0.0249 (9)
C3	0.0835 (13)	0.0586 (11)	0.0460 (10)	0.0101 (10)	−0.0026 (9)	0.0268 (9)
C4	0.0881 (13)	0.0858 (15)	0.0494 (10)	0.0291 (11)	0.0207 (10)	0.0330 (10)
C5	0.0706 (11)	0.0704 (12)	0.0559 (10)	0.0315 (9)	0.0166 (9)	0.0281 (9)
C6	0.0533 (9)	0.0446 (9)	0.0408 (8)	0.0094 (7)	0.0023 (7)	0.0167 (7)
C7	0.0536 (9)	0.0518 (10)	0.0594 (10)	0.0085 (7)	0.0032 (8)	0.0277 (8)
C8	0.0538 (9)	0.0380 (8)	0.0411 (8)	0.0099 (7)	0.0076 (7)	0.0181 (7)
C9	0.0489 (9)	0.0528 (10)	0.0709 (11)	−0.0024 (7)	−0.0039 (8)	0.0354 (9)
C10	0.0540 (10)	0.0505 (10)	0.0702 (11)	−0.0013 (8)	0.0000 (8)	0.0375 (9)
C11	0.0491 (8)	0.0407 (8)	0.0413 (8)	0.0096 (7)	0.0095 (7)	0.0183 (7)
C12	0.0481 (9)	0.0494 (9)	0.0481 (9)	0.0015 (7)	0.0031 (7)	0.0239 (8)
C13	0.0536 (9)	0.0434 (9)	0.0515 (9)	−0.0011 (7)	0.0056 (7)	0.0251 (8)
C14	0.0568 (9)	0.0432 (9)	0.0421 (8)	0.0121 (7)	0.0144 (7)	0.0198 (7)
C15	0.0556 (9)	0.0494 (9)	0.0468 (9)	0.0114 (7)	0.0077 (7)	0.0239 (8)
C16	0.0633 (10)	0.0554 (11)	0.0463 (9)	0.0246 (8)	0.0171 (8)	0.0230 (8)
C17	0.0650 (10)	0.0659 (12)	0.0482 (10)	0.0312 (9)	0.0164 (8)	0.0267 (9)
C18	0.0854 (15)	0.1060 (17)	0.0697 (12)	0.0522 (13)	0.0222 (11)	0.0510 (12)
C19	0.0787 (15)	0.128 (2)	0.0584 (13)	0.0552 (14)	0.0019 (10)	0.0304 (13)
C20	0.0648 (12)	0.0965 (17)	0.0662 (13)	0.0287 (11)	−0.0040 (10)	0.0124 (12)
O1	0.0627 (7)	0.0467 (7)	0.0560 (7)	0.0009 (5)	−0.0054 (5)	0.0302 (6)
O2	0.0605 (7)	0.0568 (7)	0.0712 (8)	0.0060 (6)	0.0086 (6)	0.0408 (7)
O3	0.0772 (9)	0.0687 (9)	0.0799 (9)	0.0223 (7)	0.0166 (7)	0.0498 (7)
O4	0.0671 (8)	0.0683 (9)	0.0576 (8)	0.0189 (7)	0.0014 (6)	0.0208 (7)

Geometric parameters (Å, º) top

C1—C6	1.373 (2)	C10—H10	0.9300
C1—C2	1.381 (2)	C11—C12	1.390 (2)
C1—H1	0.9300	C11—C14	1.469 (2)
C2—C3	1.371 (3)	C12—C13	1.373 (2)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.369 (3)	C13—H13	0.9300
C3—H3	0.9300	C14—O2	1.3000 (19)
C4—C5	1.373 (2)	C14—C15	1.391 (2)
C4—H4	0.9300	C15—C16	1.393 (2)
C5—C6	1.382 (2)	C15—H15	0.9300
C5—H5	0.9300	C16—O3	1.287 (2)
C6—C7	1.489 (2)	C16—C17	1.456 (3)
C7—O1	1.4364 (19)	C17—C18	1.347 (2)
C7—H7A	0.9700	C17—O4	1.371 (2)
C7—H7B	0.9700	C18—C19	1.408 (3)
C8—O1	1.3583 (17)	C18—H18	0.9300
C8—C9	1.379 (2)	C19—C20	1.318 (3)
C8—C13	1.386 (2)	C19—H19	0.9300
C9—C10	1.374 (2)	C20—O4	1.352 (2)
C9—H9	0.9300	C20—H20	0.9300
C10—C11	1.385 (2)	O2—H2A	1.15 (3)

C6—C1—C2	121.06 (16)	C10—C11—C14	119.56 (13)
C6—C1—H1	119.5	C12—C11—C14	123.34 (14)
C2—C1—H1	119.5	C13—C12—C11	121.39 (14)
C3—C2—C1	119.91 (17)	C13—C12—H12	119.3
C3—C2—H2	120.0	C11—C12—H12	119.3
C1—C2—H2	120.0	C12—C13—C8	120.24 (14)
C4—C3—C2	119.52 (16)	C12—C13—H13	119.9
C4—C3—H3	120.2	C8—C13—H13	119.9
C2—C3—H3	120.2	O2—C14—C15	119.95 (14)
C3—C4—C5	120.50 (17)	O2—C14—C11	116.68 (14)
C3—C4—H4	119.8	C15—C14—C11	123.37 (14)
C5—C4—H4	119.8	C14—C15—C16	121.14 (15)
C4—C5—C6	120.71 (17)	C14—C15—H15	119.4
C4—C5—H5	119.6	C16—C15—H15	119.4
C6—C5—H5	119.6	O3—C16—C15	122.40 (16)
C1—C6—C5	118.30 (15)	O3—C16—C17	116.31 (15)
C1—C6—C7	121.80 (15)	C15—C16—C17	121.28 (16)
C5—C6—C7	119.90 (15)	C18—C17—O4	109.43 (17)
O1—C7—C6	107.58 (12)	C18—C17—C16	133.19 (19)
O1—C7—H7A	110.2	O4—C17—C16	117.37 (14)
C6—C7—H7A	110.2	C17—C18—C19	106.5 (2)
O1—C7—H7B	110.2	C17—C18—H18	126.7
C6—C7—H7B	110.2	C19—C18—H18	126.7
H7A—C7—H7B	108.5	C20—C19—C18	106.89 (19)
O1—C8—C9	124.48 (14)	C20—C19—H19	126.6
O1—C8—C13	116.21 (13)	C18—C19—H19	126.6
C9—C8—C13	119.29 (14)	C19—C20—O4	111.2 (2)
C10—C9—C8	119.65 (15)	C19—C20—H20	124.4
C10—C9—H9	120.2	O4—C20—H20	124.4
C8—C9—H9	120.2	C8—O1—C7	118.05 (11)
C9—C10—C11	122.26 (15)	C14—O2—H2A	99.0 (11)
C9—C10—H10	118.9	C16—O3—H2A	95.5 (9)
C11—C10—H10	118.9	C20—O4—C17	105.94 (16)
C10—C11—C12	117.10 (14)

C6—C1—C2—C3	0.3 (3)	C12—C11—C14—O2	−178.85 (14)
C1—C2—C3—C4	−0.1 (3)	C10—C11—C14—C15	−178.45 (15)
C2—C3—C4—C5	0.0 (3)	C12—C11—C14—C15	1.4 (2)
C3—C4—C5—C6	−0.1 (3)	O2—C14—C15—C16	−2.1 (2)
C2—C1—C6—C5	−0.4 (2)	C11—C14—C15—C16	177.71 (14)
C2—C1—C6—C7	179.38 (15)	C14—C15—C16—O3	2.4 (2)
C4—C5—C6—C1	0.4 (3)	C14—C15—C16—C17	−176.10 (14)
C4—C5—C6—C7	−179.47 (17)	O3—C16—C17—C18	−3.0 (3)
C1—C6—C7—O1	−111.01 (17)	C15—C16—C17—C18	175.63 (18)
C5—C6—C7—O1	68.82 (19)	O3—C16—C17—O4	178.65 (13)
O1—C8—C9—C10	179.06 (15)	C15—C16—C17—O4	−2.7 (2)
C13—C8—C9—C10	−2.5 (3)	O4—C17—C18—C19	0.0 (2)
C8—C9—C10—C11	0.2 (3)	C16—C17—C18—C19	−178.42 (17)
C9—C10—C11—C12	1.7 (3)	C17—C18—C19—C20	0.0 (2)
C9—C10—C11—C14	−178.47 (15)	C18—C19—C20—O4	0.0 (2)
C10—C11—C12—C13	−1.3 (2)	C9—C8—O1—C7	−8.7 (2)
C14—C11—C12—C13	178.88 (14)	C13—C8—O1—C7	172.83 (13)
C11—C12—C13—C8	−1.0 (2)	C6—C7—O1—C8	−171.88 (13)
O1—C8—C13—C12	−178.53 (13)	C19—C20—O4—C17	0.0 (2)
C9—C8—C13—C12	2.9 (2)	C18—C17—O4—C20	−0.02 (19)
C10—C11—C14—O2	1.3 (2)	C16—C17—O4—C20	178.72 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	1.15 (3)	1.38 (3)	2.5030 (16)	162 (2)

Experimental details

Crystal data
Chemical formula	C₂₀H₁₆O₄
M_r	320.33
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.8927 (6), 11.3365 (11), 13.3039 (13)
α, β, γ (°)	112.111 (3), 96.687 (3), 98.638 (3)
V (Å³)	799.39 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.32 × 0.20 × 0.12

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.978, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	6611, 3439, 2268
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.147, 0.95
No. of reflections	3439
No. of parameters	220
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.29

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3	1.15 (3)	1.38 (3)	2.5030 (16)	162 (2)

Acknowledgements

The authors are grateful to Hubei Normal University for financial support.

References

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