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ISSN: 2056-9890

3-(3-Fluoro­phenyl­sulfin­yl)-5-iodo-2,7-di­methyl-1-benzo­furan

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
*Correspondence e-mail: uklee@pknu.ac.kr

(Received 30 August 2012; accepted 4 September 2012; online 8 September 2012)

In the title compound, C16H12FIO2S, the 3-fluoro­phenyl ring makes a dihedral angle of 76.47 (6)° with the mean plane [r.m.s. deviation = 0.013 (2) Å] of the benzofuran fragment. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds,forming chains along the b-axis direction, and an I⋯O contact [3.204 (2) Å]. The crystal structure also exhibits slipped ππ inter­actions between the 3-fluoro­phenyl rings of neighbouring mol­ecules [centroid–centroid distance = 3.683 (3) Å and slippage = 1.708 (3) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2008[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o486.], 2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1082.]). For a review of halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12FIO2S

  • Mr = 414.22

  • Monoclinic, P 21 /n

  • a = 8.3285 (3) Å

  • b = 15.1807 (5) Å

  • c = 12.2471 (4) Å

  • β = 90.250 (2)°

  • V = 1548.42 (9) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 2.21 mm−1

  • T = 173 K

  • 0.43 × 0.18 × 0.14 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.452, Tmax = 0.740

  • 14445 measured reflections

  • 3815 independent reflections

  • 3409 reflections with I > 2σ(I)

  • Rint = 0.035

Refinement
  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.065

  • S = 1.05

  • 3815 reflections

  • 192 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.71 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14⋯O2i 0.95 2.43 3.292 (3) 151
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

As a part of our ongoing study of 5-iodo-2,7-dimethyl-1-benzofuran derivatives containing 3-phenylsulfinyl (Choi et al., 2008) and 3-(4-fluorophenylsulfinyl) (Choi et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.013 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran fragment is 76.47 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1), and by an I···O halogen-bonding between the iodine and the oxygen of the SO unit [I1···O2ii = 3.204 (2)Å, C4—I1···O2ii = 165.03 (7)] (Politzer et al., 2007). The crystal packing (Fig. 2) also exhibits slipped ππ interactions between the 3-fluorophenyl rings of neighbouring molecules, with a Cg—Cgiii distance of 3.683 (3) Å and an interplanar distance of 3.263 (3) Å resulting in a slippage of 1.708 (3) Å (Cg is the centroid of the C11–C16 3-fluorophenyl ring).

Related literature top

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2011). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental top

3-Chloroperoxybenzoic acid (77%, 202 mg, 0.9 mmol) was added in small portions to a stirred solution of 3-(3-fluorophenylsulfanyl)-5-Iodo-2,7-dimethyl-1-benzofuran (318 mg, 0.8 mmol) in dichloromethane (30 mL) at 273 K. After being stirred at room temperature for 4h, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated at reduced pressure. The residue was purified by column chromatography (hexane–ethyl acetate, 2:1 v/v) to afford the title compound as a colorless solid [yield 74%, m.p. 445–446 K; Rf = 0.66 (hexane–ethyl acetate, 2:1 v/v)]. Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with C—H = 0.95 Å for aryl and 0.98 Å for methyl H atoms. Uiso(H) = 1.2Ueq(C) for aryl and 1.5Ueq(C) for methyl H atoms. The positions of methyl hydrogens were optimized rotationally.

Structure description top

As a part of our ongoing study of 5-iodo-2,7-dimethyl-1-benzofuran derivatives containing 3-phenylsulfinyl (Choi et al., 2008) and 3-(4-fluorophenylsulfinyl) (Choi et al., 2011) substituents, we report herein the crystal structure of the title compound.

In the title molecule (Fig. 1), the benzofuran unit is essentially planar, with a mean deviation of 0.013 (2) Å from the least-squares plane defined by the nine constituent atoms. The dihedral angle between the 3-fluorophenyl ring and the mean plane of the benzofuran fragment is 76.47 (6)°. In the crystal structure (Fig. 2), molecules are connected by weak C—H···O hydrogen bonds (Table 1), and by an I···O halogen-bonding between the iodine and the oxygen of the SO unit [I1···O2ii = 3.204 (2)Å, C4—I1···O2ii = 165.03 (7)] (Politzer et al., 2007). The crystal packing (Fig. 2) also exhibits slipped ππ interactions between the 3-fluorophenyl rings of neighbouring molecules, with a Cg—Cgiii distance of 3.683 (3) Å and an interplanar distance of 3.263 (3) Å resulting in a slippage of 1.708 (3) Å (Cg is the centroid of the C11–C16 3-fluorophenyl ring).

For background information and the crystal structures of related compounds, see: Choi et al. (2008, 2011). For a review of halogen bonding, see: Politzer et al. (2007).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are presented as small spheres of arbitrary radius.
[Figure 2] Fig. 2. A view of the C—H···O, I···O, and ππ interactions (dotted lines) in the crystal structure of the title compound. H atoms not participating in hydrogen-bonding were omitted for clarity. [Symmetry codes: (i) x - 1, y, z; (ii) x -1/2, - y + 1/2, z + 1/2; (iii) - x + 1, - y + 1, - z; (iv) x + 1, y, z; (v) x + 1/2, - y + 1/2, z - 1/2.]
3-(3-Fluorophenylsulfinyl)-5-iodo-2,7-dimethyl-1-benzofuran top
Crystal data top
C16H12FIO2SF(000) = 808
Mr = 414.22Dx = 1.777 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7687 reflections
a = 8.3285 (3) Åθ = 2.7–28.3°
b = 15.1807 (5) ŵ = 2.21 mm1
c = 12.2471 (4) ÅT = 173 K
β = 90.250 (2)°Block, colourless
V = 1548.42 (9) Å30.43 × 0.18 × 0.14 mm
Z = 4
Data collection top
Bruker SMART APEXII CCD
diffractometer
3815 independent reflections
Radiation source: rotating anode3409 reflections with I > 2σ(I)
Graphite multilayer monochromatorRint = 0.035
Detector resolution: 10.0 pixels mm-1θmax = 28.3°, θmin = 2.1°
φ and ω scansh = 1111
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
k = 2020
Tmin = 0.452, Tmax = 0.740l = 1216
14445 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.026Hydrogen site location: difference Fourier map
wR(F2) = 0.065H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0282P)2 + 0.8484P]
where P = (Fo2 + 2Fc2)/3
3815 reflections(Δ/σ)max = 0.001
192 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.71 e Å3
Crystal data top
C16H12FIO2SV = 1548.42 (9) Å3
Mr = 414.22Z = 4
Monoclinic, P21/nMo Kα radiation
a = 8.3285 (3) ŵ = 2.21 mm1
b = 15.1807 (5) ÅT = 173 K
c = 12.2471 (4) Å0.43 × 0.18 × 0.14 mm
β = 90.250 (2)°
Data collection top
Bruker SMART APEXII CCD
diffractometer
3815 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)
3409 reflections with I > 2σ(I)
Tmin = 0.452, Tmax = 0.740Rint = 0.035
14445 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0260 restraints
wR(F2) = 0.065H-atom parameters constrained
S = 1.05Δρmax = 0.48 e Å3
3815 reflectionsΔρmin = 0.71 e Å3
192 parameters
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
xyzUiso*/Ueq
I10.567756 (18)0.313250 (10)0.587900 (13)0.03495 (7)
S10.86223 (6)0.46644 (4)0.13656 (4)0.02703 (12)
F10.26520 (17)0.54480 (10)0.13600 (12)0.0441 (4)
C10.8607 (3)0.52209 (14)0.26168 (17)0.0250 (4)
O10.90716 (19)0.63275 (10)0.37911 (13)0.0289 (3)
O20.94638 (19)0.38071 (11)0.14941 (15)0.0387 (4)
C20.8029 (2)0.49449 (14)0.36768 (16)0.0238 (4)
C30.7257 (3)0.42026 (14)0.40952 (18)0.0280 (4)
H30.70210.37060.36500.034*
C40.6852 (3)0.42242 (15)0.51872 (19)0.0297 (5)
C50.7189 (3)0.49477 (16)0.58547 (18)0.0325 (5)
H50.68860.49300.66010.039*
C60.7957 (3)0.56934 (15)0.54554 (18)0.0298 (5)
C70.8348 (3)0.56539 (14)0.43646 (17)0.0260 (4)
C80.9211 (3)0.60468 (14)0.27344 (18)0.0273 (4)
C90.8290 (4)0.64909 (17)0.6148 (2)0.0420 (6)
H9A0.93980.66850.60330.063*
H9B0.81380.63420.69190.063*
H9C0.75500.69660.59430.063*
C100.9931 (3)0.66853 (15)0.1966 (2)0.0378 (6)
H10A0.99950.64200.12380.057*
H10B1.10120.68420.22180.057*
H10C0.92640.72160.19330.057*
C110.6519 (2)0.44006 (14)0.12914 (16)0.0235 (4)
C120.5369 (3)0.50573 (15)0.14214 (16)0.0272 (4)
H120.56550.56410.16240.033*
C130.3799 (3)0.48178 (16)0.12415 (17)0.0297 (5)
C140.3321 (3)0.39863 (17)0.0960 (2)0.0346 (5)
H140.22180.38490.08540.042*
C150.4494 (3)0.33527 (16)0.0835 (2)0.0366 (5)
H150.41970.27700.06380.044*
C160.6107 (3)0.35558 (16)0.09950 (19)0.0314 (5)
H160.69100.31180.09010.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.03228 (10)0.03571 (10)0.03690 (10)0.00319 (6)0.00514 (7)0.01028 (6)
S10.0235 (3)0.0315 (3)0.0261 (3)0.0005 (2)0.0032 (2)0.0058 (2)
F10.0332 (7)0.0563 (9)0.0430 (8)0.0206 (7)0.0027 (6)0.0041 (7)
C10.0253 (10)0.0242 (10)0.0254 (10)0.0023 (8)0.0001 (8)0.0024 (8)
O10.0346 (8)0.0227 (7)0.0293 (8)0.0007 (6)0.0009 (7)0.0027 (6)
O20.0259 (8)0.0370 (9)0.0530 (11)0.0077 (7)0.0050 (8)0.0157 (8)
C20.0239 (10)0.0252 (10)0.0224 (10)0.0032 (8)0.0017 (8)0.0013 (8)
C30.0303 (11)0.0250 (10)0.0287 (11)0.0007 (9)0.0003 (9)0.0012 (8)
C40.0284 (11)0.0300 (11)0.0306 (11)0.0036 (9)0.0012 (9)0.0065 (9)
C50.0383 (13)0.0366 (12)0.0227 (10)0.0081 (10)0.0016 (9)0.0006 (9)
C60.0343 (12)0.0301 (11)0.0251 (10)0.0081 (9)0.0045 (9)0.0034 (9)
C70.0280 (11)0.0225 (10)0.0275 (11)0.0046 (8)0.0031 (9)0.0010 (8)
C80.0281 (10)0.0252 (10)0.0285 (11)0.0029 (8)0.0001 (9)0.0018 (8)
C90.0573 (17)0.0371 (13)0.0316 (13)0.0050 (12)0.0034 (12)0.0101 (11)
C100.0481 (15)0.0257 (11)0.0398 (14)0.0026 (10)0.0077 (12)0.0023 (10)
C110.0226 (10)0.0282 (10)0.0198 (9)0.0014 (8)0.0017 (8)0.0016 (8)
C120.0313 (11)0.0301 (11)0.0202 (10)0.0059 (9)0.0028 (8)0.0014 (8)
C130.0260 (11)0.0419 (13)0.0214 (10)0.0121 (9)0.0035 (8)0.0034 (9)
C140.0238 (11)0.0448 (14)0.0353 (12)0.0015 (10)0.0010 (9)0.0094 (10)
C150.0317 (12)0.0314 (12)0.0466 (14)0.0049 (10)0.0017 (11)0.0078 (10)
C160.0264 (11)0.0295 (12)0.0383 (13)0.0033 (9)0.0001 (9)0.0042 (9)
Geometric parameters (Å, º) top
I1—C42.105 (2)C6—C91.503 (3)
I1—O2i3.2041 (16)C8—C101.480 (3)
S1—O21.4862 (17)C9—H9A0.9800
S1—C11.750 (2)C9—H9B0.9800
S1—C111.798 (2)C9—H9C0.9800
F1—C131.360 (2)C10—H10A0.9800
C1—C81.358 (3)C10—H10B0.9800
C1—C21.449 (3)C10—H10C0.9800
O1—C81.368 (3)C11—C161.376 (3)
O1—C71.381 (3)C11—C121.392 (3)
C2—C71.392 (3)C12—C131.374 (3)
C2—C31.396 (3)C12—H120.9500
C3—C41.381 (3)C13—C141.367 (3)
C3—H30.9500C14—C151.380 (4)
C4—C51.397 (3)C14—H140.9500
C5—C61.390 (3)C15—C161.391 (3)
C5—H50.9500C15—H150.9500
C6—C71.378 (3)C16—H160.9500
C4—I1—O2i165.03 (7)C6—C9—H9B109.5
O2—S1—C1109.58 (10)H9A—C9—H9B109.5
O2—S1—C11105.61 (10)C6—C9—H9C109.5
C1—S1—C1198.11 (10)H9A—C9—H9C109.5
C8—C1—C2107.24 (18)H9B—C9—H9C109.5
C8—C1—S1122.30 (17)C8—C10—H10A109.5
C2—C1—S1130.45 (16)C8—C10—H10B109.5
C8—O1—C7106.85 (16)H10A—C10—H10B109.5
C7—C2—C3119.29 (19)C8—C10—H10C109.5
C7—C2—C1104.80 (18)H10A—C10—H10C109.5
C3—C2—C1135.89 (19)H10B—C10—H10C109.5
C4—C3—C2116.8 (2)C16—C11—C12121.8 (2)
C4—C3—H3121.6C16—C11—S1117.57 (16)
C2—C3—H3121.6C12—C11—S1120.35 (17)
C3—C4—C5122.4 (2)C13—C12—C11116.6 (2)
C3—C4—I1119.15 (17)C13—C12—H12121.7
C5—C4—I1118.43 (17)C11—C12—H12121.7
C6—C5—C4121.7 (2)F1—C13—C14118.2 (2)
C6—C5—H5119.1F1—C13—C12117.7 (2)
C4—C5—H5119.1C14—C13—C12124.1 (2)
C7—C6—C5114.6 (2)C13—C14—C15117.8 (2)
C7—C6—C9122.6 (2)C13—C14—H14121.1
C5—C6—C9122.8 (2)C15—C14—H14121.1
C6—C7—O1124.52 (19)C14—C15—C16120.9 (2)
C6—C7—C2125.1 (2)C14—C15—H15119.5
O1—C7—C2110.33 (18)C16—C15—H15119.5
C1—C8—O1110.78 (19)C11—C16—C15118.9 (2)
C1—C8—C10133.5 (2)C11—C16—H16120.5
O1—C8—C10115.72 (19)C15—C16—H16120.5
C6—C9—H9A109.5
O2—S1—C1—C8123.85 (19)C3—C2—C7—C60.2 (3)
C11—S1—C1—C8126.32 (19)C1—C2—C7—C6178.1 (2)
O2—S1—C1—C255.4 (2)C3—C2—C7—O1178.33 (18)
C11—S1—C1—C254.4 (2)C1—C2—C7—O10.0 (2)
C8—C1—C2—C70.0 (2)C2—C1—C8—O10.1 (2)
S1—C1—C2—C7179.29 (17)S1—C1—C8—O1179.29 (15)
C8—C1—C2—C3177.8 (2)C2—C1—C8—C10178.4 (2)
S1—C1—C2—C32.8 (4)S1—C1—C8—C102.2 (4)
C7—C2—C3—C40.1 (3)C7—O1—C8—C10.1 (2)
C1—C2—C3—C4177.6 (2)C7—O1—C8—C10178.6 (2)
C2—C3—C4—C50.0 (3)O2—S1—C11—C1621.3 (2)
C2—C3—C4—I1179.77 (15)C1—S1—C11—C16134.30 (18)
O2i—I1—C4—C334.5 (4)O2—S1—C11—C12165.15 (17)
O2i—I1—C4—C5145.8 (2)C1—S1—C11—C1252.11 (19)
C3—C4—C5—C60.0 (4)C16—C11—C12—C130.2 (3)
I1—C4—C5—C6179.77 (17)S1—C11—C12—C13173.49 (15)
C4—C5—C6—C70.1 (3)C11—C12—C13—F1179.81 (18)
C4—C5—C6—C9178.2 (2)C11—C12—C13—C140.7 (3)
C5—C6—C7—O1178.1 (2)F1—C13—C14—C15179.6 (2)
C9—C6—C7—O10.2 (3)C12—C13—C14—C150.9 (4)
C5—C6—C7—C20.1 (3)C13—C14—C15—C160.2 (4)
C9—C6—C7—C2178.1 (2)C12—C11—C16—C150.8 (3)
C8—O1—C7—C6178.1 (2)S1—C11—C16—C15174.31 (19)
C8—O1—C7—C20.1 (2)C14—C15—C16—C110.6 (4)
Symmetry code: (i) x1/2, y+1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2ii0.952.433.292 (3)151
Symmetry code: (ii) x1, y, z.

Experimental details

Crystal data
Chemical formulaC16H12FIO2S
Mr414.22
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)8.3285 (3), 15.1807 (5), 12.2471 (4)
β (°) 90.250 (2)
V3)1548.42 (9)
Z4
Radiation typeMo Kα
µ (mm1)2.21
Crystal size (mm)0.43 × 0.18 × 0.14
Data collection
DiffractometerBruker SMART APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.452, 0.740
No. of measured, independent and
observed [I > 2σ(I)] reflections
14445, 3815, 3409
Rint0.035
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.026, 0.065, 1.05
No. of reflections3815
No. of parameters192
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.71

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14···O2i0.952.433.292 (3)151.1
Symmetry code: (i) x1, y, z.
 

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

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