4-(Benzo­furan-2-yl)-2-[3-(4-chloro­phen­yl)-5-(4-fluoro­phen­yl)-4,5-di­hydro-1H-pyrazol-1-yl]thia­zole

El-Hiti, G.A.; Abdel-Wahab, B.F.; Alqahtani, A.; Hegazy, A.S.; Kariuki, B.M.

doi:10.1107/S2414314619003596

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 3| March 2019| x190359

https://doi.org/10.1107/S2414314619003596

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4-(Benzofuran-2-yl)-2-[3-(4-chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]thiazole

Gamal A. El-Hiti,^a ^* Bakr F. Abdel-Wahab,^b,^c Alaa Alqahtani,^d Amany S. Hegazy ^e and Benson M. Kariuki ^e ^*

^aDepartment of Optometry, College of Applied Medical Sciences, King Saud University, PO Box 10219, Riyadh 11433, Saudi Arabia, ^bDepartment of Chemistry, College of Science and Humanities, Shaqra University, Duwadimi, Saudi Arabia, ^cApplied Organic Chemistry Department, National Research Centre, Dokki, Giza, Egypt, ^dPharmaceutical Chemistry Department, College of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia, and ^eSchool of Chemistry, Cardiff University, Main Building, Park Place, Cardiff CF10 3AT, Wales
^*Correspondence e-mail: gelhiti@ksu.edu.sa, kariukib@cardiff.ac.uk

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 13 March 2019; accepted 14 March 2019; online 20 March 2019)

The molecule of the title compound, C₂₆H₁₇ClFN₃OS, comprises benzofuranyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) ring systems. Rings A–D are almost coplanar, as indicated by the twist angles between the ring pairs A/B, B/C and C/D of 7.6 (1), 4.7 (1) and 6.9 (2)°, respectively. Ring E is twisted by 73.2 (1)° from the plane through ring C. In the crystal, pairwise C—H⋯F interactions link the molecules into inversion dimers. Aromatic π–π interactions are also observed between rings A and E and between rings B and C for neighbouring pairs of molecules related by inversion symmetry. Taken together, the weak interactions generate [010] chains.

Keywords: crystal structure; benzofuran; thiazole; pyrazole.

CCDC reference: 1903156

Structure description

Compounds containing a benzofuran moiety are present in many important natural products and drugs (Naik et al., 2015 ). In addition, thiazoles and pyrazoles are an essential core scaffold in many natural products and have various biological activities (Chhabria et al., 2016 ; Faria et al., 2017 ). Therefore, the synthesis, characterization and applications of compounds containing such heterocycles are of continued interest and we describe here the synthesis and structure of the title compound.

The molecule of the title compound comprises benzofuranyl (A), thiazolyl (B), pyrazolyl (C), chlorophenyl (D) and fluorophenyl (E) ring systems (Fig. 1). Rings A–D are almost coplanar, as indicated by the twist angles between the ring pairs A/B, B/C and C/D of 7.6 (1), 4.7 (1) and 6.9 (2)°, respectively. Ring E is twisted by 73.2 (1)° from the plane through ring C. In the arbitrarily-chosen asymmetric unit, the stereogenic centre C12 has an S configuration, but crystal symmetry generates a racemic mixture.

Figure 1
The molecular structure of the title compound showing 50% probability displacement ellipsoids.

In the crystal, pairwise C—H⋯F interactions link molecules into inversion dimers (Table 1). Aromatic π–π interactions are also observed between rings A and E [centroid–centroid separation = 3.755 (2) Å] and between rings B and C [3.796 (2) Å] for neighbouring pairs of molecules related by inversion symmetry; this results in each pair of molecules being linked by four π–π interactions (Fig. 2). The combination of C—H⋯F and π–π interactions generates [010] chains.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯F1ⁱ	0.93	2.58	3.254 (5)	130
Symmetry code: (i) -x-1, -y+1, -z.

Figure 2
A view of the crystal structure down the a axis, showing π–π contacts as green dotted lines and C—H⋯F contacts in red.

Synthesis and crystallization

The title compound was synthesized from the condensation of molar equivalents of 3-(4-chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide with 1-(benzofuran-2-yl)-2-bromoethanone in anhydrous ethanol under reflux for 2 h. The crude product was recrystallized from dimethylformamide solution to give colourless needles (yield 74%, m.p. 234–236 °C).

Refinement

All H atoms were placed in calculated positions and refined using a riding model. Bond lengths were set at 0.98, 0.97 and 0.93 Å for methine, methylene and aromatic C—H H atoms, respectively, with their U_iso(H) values set at 1.2 times the U_eq of the atom to which they are bonded. Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₆H₁₇ClFN₃OS
M_r	473.93
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	6.6631 (6), 15.2297 (17), 22.431 (3)
β (°)	96.390 (9)
V (Å³)	2262.1 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.29
Crystal size (mm)	0.46 × 0.19 × 0.11

Data collection
Diffractometer	Rigaku OD SuperNova Dual source diffractometer with an Atlas detector
Absorption correction	Gaussian (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, Oxfordshire, England.]$ )
T_min, T_max	0.990, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	10799, 4617, 2323
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.171, 1.03
No. of reflections	4617
No. of parameters	298
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.21
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, Oxfordshire, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL2018 (Sheldrick, 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), and CHEMDRAW Ultra (Cambridge Soft, 2001 ).

Structural data

CCDC reference: 1903156

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619003596/hb4289sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619003596/hb4289Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619003596/hb4289Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows and WinGX (Farrugia, 2012); software used to prepare material for publication: ORTEP-3 for Windows and WinGX (Farrugia, 2012), and CHEMDRAW Ultra (Cambridge Soft, 2001).

4-(Benzofuran-2-yl)-2-[3-(4-chlorophenyl)-5-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl]thiazole top

Crystal data top

C₂₆H₁₇ClFN₃OS	F(000) = 976
M_r = 473.93	D_x = 1.392 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 6.6631 (6) Å	Cell parameters from 1999 reflections
b = 15.2297 (17) Å	θ = 3.7–23.3°
c = 22.431 (3) Å	µ = 0.29 mm⁻¹
β = 96.390 (9)°	T = 296 K
V = 2262.1 (4) Å³	Needle, colourless
Z = 4	0.46 × 0.19 × 0.11 mm

Data collection top

Rigaku OD SuperNova Dual source diffractometer with an Atlas detector	2323 reflections with I > 2σ(I)
ω scans	R_int = 0.042
Absorption correction: gaussian (CrysAlis PRO; Rigaku OD, 2015)	θ_max = 26.4°, θ_min = 3.4°
T_min = 0.990, T_max = 0.997	h = −6→8
10799 measured reflections	k = −19→17
4617 independent reflections	l = −28→22

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.060	H-atom parameters constrained
wR(F²) = 0.171	w = 1/[σ²(F_o²) + (0.0542P)² + 0.6825P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
4617 reflections	Δρ_max = 0.17 e Å⁻³
298 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.

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

	x	y	z	U_iso*/U_eq
C1	−0.0420 (5)	0.9153 (2)	0.16557 (14)	0.0617 (8)
C2	−0.2264 (5)	0.8840 (2)	0.17209 (15)	0.0666 (9)
H2	−0.315276	0.858931	0.141930	0.080*
C3	−0.2636 (5)	0.8956 (2)	0.23330 (15)	0.0659 (9)
C4	−0.0873 (5)	0.9353 (2)	0.26072 (16)	0.0669 (9)
C5	−0.4193 (6)	0.8785 (3)	0.26796 (18)	0.0805 (11)
H5	−0.538290	0.852152	0.251208	0.097*
C6	−0.3937 (7)	0.9014 (3)	0.32729 (19)	0.0923 (12)
H6	−0.497815	0.891053	0.350794	0.111*
C7	−0.2172 (8)	0.9393 (3)	0.35304 (18)	0.0948 (13)
H7	−0.204363	0.952927	0.393693	0.114*
C8	−0.0587 (7)	0.9576 (3)	0.32022 (18)	0.0898 (12)
H8	0.060249	0.983506	0.337468	0.108*
C9	0.0725 (5)	0.9187 (2)	0.11473 (14)	0.0591 (8)
C10	0.2685 (5)	0.9408 (2)	0.11469 (16)	0.0712 (10)
H10	0.351786	0.959633	0.148300	0.085*
C11	0.1001 (5)	0.8959 (2)	0.01989 (16)	0.0637 (8)
C12	−0.1510 (5)	0.8293 (2)	−0.05800 (15)	0.0661 (9)
H12	−0.261981	0.869744	−0.052668	0.079*
C13	−0.1304 (5)	0.8178 (3)	−0.12471 (15)	0.0810 (11)
H13A	−0.154473	0.757287	−0.137032	0.097*
H13B	−0.224552	0.855387	−0.148931	0.097*
C14	0.0830 (5)	0.8439 (2)	−0.13025 (15)	0.0601 (8)
C15	−0.1805 (5)	0.7438 (2)	−0.02572 (14)	0.0602 (8)
C16	−0.0221 (6)	0.6941 (3)	0.00002 (18)	0.0819 (11)
H16	0.109071	0.713957	−0.001787	0.098*
C17	−0.0516 (6)	0.6161 (3)	0.02832 (19)	0.0900 (12)
H17	0.057272	0.583478	0.045913	0.108*
C18	−0.2429 (8)	0.5880 (3)	0.02992 (16)	0.0842 (12)
C19	−0.4061 (6)	0.6335 (3)	0.00476 (17)	0.0840 (12)
H19	−0.536128	0.611895	0.005850	0.101*
C20	−0.3735 (5)	0.7132 (3)	−0.02265 (15)	0.0706 (10)
H20	−0.483302	0.746331	−0.039096	0.085*
C21	0.1776 (5)	0.8416 (2)	−0.18589 (14)	0.0599 (8)
C22	0.0785 (6)	0.8020 (2)	−0.23703 (17)	0.0777 (10)
H22	−0.047482	0.776451	−0.235296	0.093*
C23	0.1650 (7)	0.8002 (3)	−0.29021 (18)	0.0883 (12)
H23	0.097113	0.774069	−0.324130	0.106*
C24	0.3519 (6)	0.8371 (3)	−0.29268 (17)	0.0790 (11)
C25	0.4505 (5)	0.8776 (3)	−0.24365 (18)	0.0794 (11)
H25	0.575572	0.903742	−0.245998	0.095*
C26	0.3637 (5)	0.8797 (2)	−0.19036 (16)	0.0706 (9)
H26	0.431759	0.907147	−0.157005	0.085*
N1	−0.0258 (4)	0.89273 (19)	0.06012 (12)	0.0645 (7)
N3	0.0437 (4)	0.8709 (2)	−0.03768 (13)	0.0748 (8)
N4	0.1770 (4)	0.87408 (18)	−0.08051 (12)	0.0629 (7)
O1	0.0500 (3)	0.94806 (16)	0.21956 (10)	0.0709 (6)
Cl1	0.4626 (2)	0.83256 (9)	−0.35884 (5)	0.1214 (5)
F1	−0.2761 (5)	0.51028 (17)	0.05775 (12)	0.1259 (10)
S1	0.34414 (13)	0.92974 (7)	0.04410 (4)	0.0766 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.063 (2)	0.063 (2)	0.056 (2)	0.0041 (17)	−0.0049 (16)	−0.0023 (16)
C2	0.066 (2)	0.071 (2)	0.060 (2)	0.0049 (18)	−0.0033 (17)	−0.0044 (17)
C3	0.071 (2)	0.062 (2)	0.062 (2)	0.0090 (18)	−0.0027 (18)	0.0024 (17)
C4	0.075 (2)	0.065 (2)	0.059 (2)	0.0109 (18)	−0.0007 (18)	0.0038 (17)
C5	0.085 (3)	0.084 (3)	0.072 (3)	0.000 (2)	0.008 (2)	0.009 (2)
C6	0.115 (3)	0.093 (3)	0.071 (3)	0.009 (3)	0.019 (3)	0.016 (2)
C7	0.132 (4)	0.093 (3)	0.058 (2)	0.006 (3)	0.009 (3)	0.002 (2)
C8	0.110 (3)	0.093 (3)	0.063 (3)	−0.003 (3)	−0.006 (2)	−0.007 (2)
C9	0.0597 (18)	0.059 (2)	0.057 (2)	0.0007 (16)	0.0008 (16)	0.0016 (16)
C10	0.068 (2)	0.077 (2)	0.067 (2)	−0.0116 (19)	0.0042 (17)	−0.0081 (18)
C11	0.070 (2)	0.058 (2)	0.063 (2)	−0.0065 (17)	0.0039 (18)	0.0037 (17)
C12	0.0570 (18)	0.077 (2)	0.063 (2)	−0.0064 (18)	0.0009 (16)	−0.0006 (18)
C13	0.072 (2)	0.109 (3)	0.061 (2)	−0.021 (2)	0.0003 (18)	0.009 (2)
C14	0.0591 (18)	0.056 (2)	0.063 (2)	−0.0051 (16)	−0.0002 (16)	0.0059 (16)
C15	0.0571 (18)	0.072 (2)	0.0513 (19)	−0.0030 (18)	0.0052 (15)	−0.0078 (16)
C16	0.067 (2)	0.081 (3)	0.096 (3)	−0.007 (2)	0.001 (2)	0.005 (2)
C17	0.090 (3)	0.078 (3)	0.098 (3)	0.000 (2)	−0.010 (2)	0.002 (2)
C18	0.122 (4)	0.073 (3)	0.057 (2)	−0.016 (3)	0.004 (2)	0.0010 (19)
C19	0.082 (3)	0.098 (3)	0.075 (3)	−0.027 (2)	0.023 (2)	−0.009 (2)
C20	0.061 (2)	0.086 (3)	0.065 (2)	−0.005 (2)	0.0091 (17)	−0.0046 (19)
C21	0.068 (2)	0.0521 (19)	0.058 (2)	−0.0010 (16)	0.0029 (16)	0.0048 (16)
C22	0.088 (3)	0.073 (2)	0.071 (3)	−0.016 (2)	0.004 (2)	0.000 (2)
C23	0.116 (3)	0.083 (3)	0.064 (3)	−0.006 (3)	0.002 (2)	−0.006 (2)
C24	0.099 (3)	0.075 (3)	0.064 (2)	0.013 (2)	0.016 (2)	0.008 (2)
C25	0.071 (2)	0.096 (3)	0.072 (3)	0.003 (2)	0.012 (2)	0.013 (2)
C26	0.068 (2)	0.077 (2)	0.067 (2)	−0.0017 (19)	0.0035 (18)	0.0026 (18)
N1	0.0649 (16)	0.0714 (19)	0.0562 (17)	−0.0042 (14)	0.0018 (14)	−0.0032 (14)
N3	0.0708 (18)	0.095 (2)	0.0586 (18)	−0.0241 (16)	0.0089 (15)	−0.0044 (16)
N4	0.0627 (16)	0.0638 (18)	0.0622 (18)	−0.0054 (14)	0.0064 (14)	−0.0006 (14)
O1	0.0718 (14)	0.0755 (16)	0.0627 (15)	−0.0045 (12)	−0.0045 (12)	−0.0076 (12)
Cl1	0.1498 (11)	0.1418 (12)	0.0796 (8)	0.0282 (9)	0.0433 (7)	0.0075 (7)
F1	0.176 (3)	0.0949 (19)	0.105 (2)	−0.0308 (18)	0.0060 (17)	0.0190 (15)
S1	0.0685 (6)	0.0863 (7)	0.0745 (6)	−0.0181 (5)	0.0061 (5)	−0.0031 (5)

Geometric parameters (Å, º) top

C1—C2	1.341 (4)	C13—H13A	0.9700
C1—O1	1.388 (4)	C13—H13B	0.9700
C1—C9	1.442 (4)	C14—N4	1.301 (4)
C2—C3	1.433 (4)	C14—C21	1.460 (4)
C2—H2	0.9300	C15—C16	1.372 (5)
C3—C5	1.389 (5)	C15—C20	1.377 (4)
C3—C4	1.401 (5)	C16—C17	1.372 (5)
C4—C8	1.370 (5)	C16—H16	0.9300
C4—O1	1.384 (4)	C17—C18	1.349 (5)
C5—C6	1.368 (5)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.358 (5)
C6—C7	1.378 (6)	C18—F1	1.367 (4)
C6—H6	0.9300	C19—C20	1.389 (5)
C7—C8	1.381 (6)	C19—H19	0.9300
C7—H7	0.9300	C20—H20	0.9300
C8—H8	0.9300	C21—C26	1.383 (4)
C9—C10	1.350 (4)	C21—C22	1.396 (5)
C9—N1	1.381 (4)	C22—C23	1.382 (5)
C10—S1	1.722 (4)	C22—H22	0.9300
C10—H10	0.9300	C23—C24	1.373 (5)
C11—N1	1.300 (4)	C23—H23	0.9300
C11—N3	1.359 (4)	C24—C25	1.365 (5)
C11—S1	1.734 (3)	C24—Cl1	1.731 (4)
C12—N3	1.470 (4)	C25—C26	1.385 (5)
C12—C15	1.513 (5)	C25—H25	0.9300
C12—C13	1.528 (5)	C26—H26	0.9300
C12—H12	0.9800	N3—N4	1.380 (3)
C13—C14	1.495 (4)

C2—C1—O1	110.7 (3)	N4—C14—C13	113.2 (3)
C2—C1—C9	132.1 (3)	C21—C14—C13	124.7 (3)
O1—C1—C9	117.1 (3)	C16—C15—C20	118.1 (3)
C1—C2—C3	108.6 (3)	C16—C15—C12	122.7 (3)
C1—C2—H2	125.7	C20—C15—C12	119.1 (3)
C3—C2—H2	125.7	C17—C16—C15	121.9 (4)
C5—C3—C4	118.5 (3)	C17—C16—H16	119.0
C5—C3—C2	137.1 (4)	C15—C16—H16	119.0
C4—C3—C2	104.4 (3)	C18—C17—C16	118.1 (4)
C8—C4—O1	125.8 (4)	C18—C17—H17	120.9
C8—C4—C3	123.6 (4)	C16—C17—H17	120.9
O1—C4—C3	110.6 (3)	C17—C18—C19	122.8 (4)
C6—C5—C3	118.5 (4)	C17—C18—F1	119.2 (4)
C6—C5—H5	120.7	C19—C18—F1	118.0 (4)
C3—C5—H5	120.7	C18—C19—C20	118.3 (4)
C5—C6—C7	121.5 (4)	C18—C19—H19	120.9
C5—C6—H6	119.3	C20—C19—H19	120.9
C7—C6—H6	119.3	C15—C20—C19	120.7 (4)
C6—C7—C8	121.9 (4)	C15—C20—H20	119.7
C6—C7—H7	119.0	C19—C20—H20	119.7
C8—C7—H7	119.0	C26—C21—C22	117.9 (3)
C4—C8—C7	115.9 (4)	C26—C21—C14	121.9 (3)
C4—C8—H8	122.0	C22—C21—C14	120.2 (3)
C7—C8—H8	122.0	C23—C22—C21	120.9 (3)
C10—C9—N1	115.8 (3)	C23—C22—H22	119.5
C10—C9—C1	127.4 (3)	C21—C22—H22	119.5
N1—C9—C1	116.8 (3)	C24—C23—C22	119.6 (4)
C9—C10—S1	111.0 (3)	C24—C23—H23	120.2
C9—C10—H10	124.5	C22—C23—H23	120.2
S1—C10—H10	124.5	C25—C24—C23	120.7 (3)
N1—C11—N3	121.2 (3)	C25—C24—Cl1	119.7 (3)
N1—C11—S1	116.7 (3)	C23—C24—Cl1	119.6 (3)
N3—C11—S1	122.1 (3)	C24—C25—C26	119.7 (4)
N3—C12—C15	112.3 (3)	C24—C25—H25	120.1
N3—C12—C13	100.4 (3)	C26—C25—H25	120.1
C15—C12—C13	113.6 (3)	C21—C26—C25	121.2 (3)
N3—C12—H12	110.1	C21—C26—H26	119.4
C15—C12—H12	110.1	C25—C26—H26	119.4
C13—C12—H12	110.1	C11—N1—C9	109.0 (3)
C14—C13—C12	103.9 (3)	C11—N3—N4	121.3 (3)
C14—C13—H13A	111.0	C11—N3—C12	123.9 (3)
C12—C13—H13A	111.0	N4—N3—C12	114.4 (3)
C14—C13—H13B	111.0	C14—N4—N3	107.4 (3)
C12—C13—H13B	111.0	C4—O1—C1	105.7 (3)
H13A—C13—H13B	109.0	C10—S1—C11	87.54 (17)
N4—C14—C21	122.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···F1ⁱ	0.93	2.58	3.254 (5)	130

Symmetry code: (i) −x−1, −y+1, −z.

Acknowledgements

The authors thank Umm Al-Qura and Cardiff Universities for their ongoing support.

Funding information

Funding for this research was provided by: Deanship of Scientific Research at Umm Al-Qura University (grant No. 17-MED-1-03-0007 to AA).

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