2-(10-Bromo­anthracen-9-yl)-N-phenyl­aniline

Saravanan, D.; Ponraj, C.; Khamrang, T.; Hemamalini, M.; Antony, G.J.M.

doi:10.1107/S2414314624004759

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 9| Part 5| May 2024| x240475

https://doi.org/10.1107/S2414314624004759

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2-(10-Bromoanthracen-9-yl)-N-phenylaniline

Dhandayutham Saravanan,^a C. Ponraj,^a Themmila Khamrang,^b Madhukar Hemamalini ^c and G. Jerald Maria Antony ^a ^*

^aDepartment of Chemistry, National College, Thiruchirappalli, Tamil Nadu, India, ^bDepartment of Chemistry, Dhanamanjuri University, Manipur 795 001, India, and ^cDepartment of Chemistry, Mother Teresa Women's University, Kodaikanal, Tamil Nadu, India
^*Correspondence e-mail: jerelewin.mine@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 13 May 2024; accepted 21 May 2024; online 31 May 2024)

In the title compound, C₂₆H₁₈BrN, the central benzene ring makes dihedral angles with its adjacent anthracene ring system and pendant benzene ring of 87.49 (13) and 62.01 (17)°, respectively. The N—H moiety is sterically blocked from forming a hydrogen bond, but weak C—H⋯π interactions occur in the extended structure.

Keywords: crystal structure; C—H⋯π interactions.

CCDC reference: 2356945

Structure description

Anthracene derivatives are candidates for two-dimensional molecular crystals, which can show interesting properties with applications in electronics, biomedicine, and sensors (Yan et al., 2023 ). As part of our studies of anthracene derivatives, we now report the synthesis and crystal structure of the title compound, C₂₆H₁₈BrN, (I).

The molecular structure of (I) is illustrated in Fig. 1. As expected, the anthracene (C1–C14) ring system is almost planar, with a maximum deviation of 0.039 (4) Å for atom C1. The central benzene (C15–C20) ring makes dihedral angles of 87.49 (13) and 62.01 (17)° with the anthracene ring system and the terminal C21–C26 phenyl ring, respectively. The dihedral angle between the phenyl ring and anthracene ring system is 87.92 (14)°.

Figure 1
The molecular structure of (I) showing displacement ellipsoids at the 50% probability level (H atoms are omitted for clarity).

In the extended structure, the N—H grouping in (I) is presumably blocked from forming a hydrogen bond due to steric reasons but two weak C—H⋯π interactions are observed (Table 1). The packing is illustrated in Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯Cg3ⁱ	0.93	2.77	3.598 (4)	148
C18—H18⋯Cg5ⁱ	0.93	2.85	3.661 (4)	146
Symmetry code: (i) .

Figure 2
The crystal packing of (I) viewed approximately down [000].

Related structures reported in the Cambridge Structural Database (CSD, Version 5.41, updated November 2019; Groom et al., 2016 ) include {1-[2-(9-anthryl)phenyl]-3-[2-(4-isopropyl-4,5-dihydro-1,3-oxazol-2-yl)propan-2-yl]-1,3-dihydro-2H-benzimidazole-2-thione}dichloropalladium(II) deuterochloroform solvate (CSD refcode BUVGEF; Gao et al. 2010 ), 10-bromo-2,7-di-tert-butyl-N,N-bis(4-methylphenyl) anthracen-9-amine (FEKTOG; Hoffend et al., 2012 ) and 9-(10′-bromo-9′-anthryl)carbazole (PEDSUM; Boyer et al., 1993 ).

Synthesis and crystallization

Following the method of Justin Thomas et al. (2005 ), a mixture of diphenylamine (1.69 g, 10.0 mmol), sodium tert-butoxide (1.15 g, 12.0 mmol) and Pd₂(dba)₃ (dba = dibenzylideneacetone; 23 mg, 0.10 mmol) was dissolved in dry toluene (50 ml), and 9,10-dibromoanthracene (3.33 g, 10.0 mmol) and 1,1′-ferrocenediyl-bis(diphenylphosphine) (0.277 g, 0.5 mmol) were added sequentially. The mixture was heated to reflux, stirred for 24 h and then cooled and 5 ml of water were added. The solution was extracted with dichloromethane/water. The organic layer was dried over anhydrous sodium sulfate, filtered, and dried. The residue was chromatographed through silica gel using a mixture of dichloromethane and hexane as the eluent to give the pure product as yellow crystals.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₆H₁₈BrN
M_r	424.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.0619 (17), 7.6891 (10), 20.475 (3)
β (°)	106.809 (14)
V (Å³)	1968.6 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.10
Crystal size (mm)	0.48 × 0.39 × 0.30

Data collection
Diffractometer	Agilent Xcalibur, Atlas, Gemini
Absorption correction	Analytical (CrysAlis RED; Agilent, 2012 )
T_min, T_max	0.432, 0.572
No. of measured, independent and observed [I > 2σ(I)] reflections	12046, 3999, 3115
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.129, 1.05
No. of reflections	3999
No. of parameters	257
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.81, −1.40
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2356945

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314624004759/hb4471sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624004759/hb4471Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314624004759/hb4471Isup3.cml

checkCIF report

Computing details top

2-(10-Bromoanthracen-9-yl)-N-phenylaniline top

Crystal data top

C₂₆H₁₈BrN	F(000) = 864
M_r = 424.32	D_x = 1.432 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 13.0619 (17) Å	Cell parameters from 3999 reflections
b = 7.6891 (10) Å	θ = 3.4–26.4°
c = 20.475 (3) Å	µ = 2.10 mm⁻¹
β = 106.809 (14)°	T = 293 K
V = 1968.6 (5) Å³	Plate, yellow
Z = 4	0.48 × 0.39 × 0.30 mm

Data collection top

Agilent Xcalibur, Atlas, Gemini diffractometer	3115 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.037
ω scans	θ_max = 26.4°, θ_min = 3.4°
Absorption correction: analytical (CrysAlis RED; Agilent, 2012)	h = −16→14
T_min = 0.432, T_max = 0.572	k = −9→8
12046 measured reflections	l = −25→25
3999 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0558P)² + 1.6534P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3999 reflections	Δρ_max = 0.81 e Å⁻³
257 parameters	Δρ_min = −1.40 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. The N-bound hydrogen atom was located in a difference map and its position was freely refined. The remaining hydrogen atoms were positioned geometrically [C—H = 0.93 Å] and were refined using a riding model, with U_iso(H) = 1.2 or 1.5U_eq(C).

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

	x	y	z	U_iso*/U_eq
Br1	−0.02528 (3)	−0.04566 (6)	0.34351 (2)	0.0715 (2)
N1	0.4598 (2)	0.3135 (4)	0.41519 (18)	0.0577 (9)
C3	0.1079 (2)	0.2407 (4)	0.40118 (14)	0.0324 (6)
C12	0.1886 (2)	0.3680 (4)	0.40287 (14)	0.0315 (6)
C11	0.2396 (2)	0.3735 (4)	0.35115 (14)	0.0309 (6)
C5	0.1305 (2)	0.1255 (4)	0.29426 (14)	0.0321 (6)
C10	0.2127 (2)	0.2523 (4)	0.29757 (14)	0.0306 (6)
C4	0.0816 (2)	0.1236 (4)	0.34678 (15)	0.0346 (6)
C15	0.3228 (2)	0.5092 (4)	0.35332 (15)	0.0338 (6)
C9	0.2637 (2)	0.2517 (4)	0.24464 (15)	0.0396 (7)
H9	0.317747	0.331703	0.246104	0.048*
C20	0.4302 (2)	0.4749 (4)	0.38369 (16)	0.0374 (7)
C2	0.0601 (3)	0.2382 (4)	0.45579 (15)	0.0424 (7)
H2	0.007271	0.156905	0.455513	0.051*
C8	0.2351 (3)	0.1373 (4)	0.19247 (16)	0.0467 (8)
H8	0.269377	0.139879	0.158491	0.056*
C21	0.5558 (2)	0.2265 (4)	0.41906 (17)	0.0410 (7)
C13	0.2159 (3)	0.4878 (4)	0.45853 (16)	0.0426 (7)
H13	0.267045	0.573083	0.460148	0.051*
C6	0.1034 (3)	0.0083 (4)	0.23773 (16)	0.0426 (7)
H6	0.049834	−0.073800	0.234413	0.051*
C7	0.1544 (3)	0.0148 (4)	0.18900 (17)	0.0487 (8)
H7	0.135678	−0.063095	0.152715	0.058*
C16	0.2937 (3)	0.6726 (4)	0.32505 (18)	0.0478 (8)
H16	0.221626	0.697953	0.305740	0.057*
C26	0.6048 (3)	0.1311 (4)	0.47645 (18)	0.0482 (8)
H26	0.576252	0.129337	0.513136	0.058*
C18	0.4752 (3)	0.7621 (4)	0.35375 (18)	0.0501 (8)
H18	0.526590	0.845360	0.353300	0.060*
C1	0.0911 (3)	0.3530 (5)	0.50787 (16)	0.0484 (8)
H1	0.060381	0.347710	0.543532	0.058*
C19	0.5059 (3)	0.6027 (4)	0.38339 (19)	0.0492 (8)
H19	0.578117	0.579804	0.403488	0.059*
C22	0.6002 (3)	0.2280 (5)	0.36512 (19)	0.0512 (8)
H22	0.567577	0.291351	0.325915	0.061*
C17	0.3693 (3)	0.7984 (4)	0.32496 (19)	0.0545 (9)
H17	0.348321	0.906707	0.305481	0.065*
C14	0.1681 (3)	0.4789 (5)	0.50894 (17)	0.0497 (8)
H14	0.187045	0.558049	0.544786	0.060*
C23	0.6920 (3)	0.1364 (5)	0.3695 (2)	0.0620 (10)
H23	0.721646	0.139989	0.333358	0.074*
C25	0.6966 (3)	0.0379 (5)	0.4793 (3)	0.0678 (12)
H25	0.729331	−0.027472	0.517943	0.081*
C24	0.7402 (3)	0.0409 (5)	0.4254 (3)	0.0717 (12)
H24	0.801947	−0.021919	0.427468	0.086*
H55	0.425 (3)	0.265 (6)	0.435 (2)	0.073 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0704 (3)	0.0804 (3)	0.0719 (3)	−0.0470 (2)	0.0336 (2)	−0.0247 (2)
N1	0.0311 (15)	0.0545 (18)	0.092 (2)	0.0093 (13)	0.0244 (16)	0.0365 (17)
C3	0.0271 (14)	0.0351 (15)	0.0330 (15)	0.0021 (11)	0.0057 (11)	0.0035 (12)
C12	0.0279 (14)	0.0333 (14)	0.0306 (15)	0.0019 (11)	0.0041 (11)	0.0025 (11)
C11	0.0212 (13)	0.0327 (14)	0.0357 (15)	0.0024 (11)	0.0036 (11)	0.0057 (12)
C5	0.0284 (14)	0.0309 (14)	0.0329 (15)	0.0031 (11)	0.0024 (12)	0.0014 (11)
C10	0.0255 (13)	0.0326 (14)	0.0314 (14)	0.0047 (11)	0.0047 (11)	0.0053 (11)
C4	0.0260 (14)	0.0365 (15)	0.0378 (16)	−0.0035 (12)	0.0039 (12)	0.0021 (12)
C15	0.0315 (15)	0.0330 (14)	0.0371 (16)	−0.0015 (12)	0.0103 (13)	0.0024 (12)
C9	0.0374 (16)	0.0413 (17)	0.0415 (17)	0.0049 (13)	0.0136 (14)	0.0070 (13)
C20	0.0315 (15)	0.0360 (15)	0.0465 (18)	0.0015 (12)	0.0140 (13)	0.0089 (13)
C2	0.0389 (17)	0.0494 (18)	0.0401 (17)	−0.0023 (14)	0.0133 (14)	0.0030 (14)
C8	0.052 (2)	0.054 (2)	0.0379 (17)	0.0078 (16)	0.0188 (15)	0.0020 (15)
C21	0.0286 (15)	0.0322 (15)	0.059 (2)	−0.0012 (12)	0.0069 (14)	0.0050 (14)
C13	0.0433 (18)	0.0419 (17)	0.0410 (18)	−0.0080 (14)	0.0098 (14)	−0.0061 (13)
C6	0.0469 (18)	0.0389 (16)	0.0379 (17)	−0.0039 (14)	0.0059 (14)	−0.0037 (13)
C7	0.062 (2)	0.0439 (18)	0.0373 (18)	0.0047 (16)	0.0093 (16)	−0.0058 (14)
C16	0.0389 (17)	0.0378 (17)	0.061 (2)	0.0031 (14)	0.0050 (15)	0.0133 (15)
C26	0.0388 (17)	0.0457 (18)	0.056 (2)	0.0000 (14)	0.0074 (15)	0.0072 (16)
C18	0.051 (2)	0.0384 (18)	0.065 (2)	−0.0136 (15)	0.0232 (18)	0.0003 (15)
C1	0.0504 (19)	0.060 (2)	0.0377 (18)	0.0041 (16)	0.0181 (15)	−0.0013 (15)
C19	0.0313 (16)	0.0508 (19)	0.066 (2)	−0.0044 (14)	0.0145 (16)	0.0070 (17)
C22	0.049 (2)	0.0476 (19)	0.056 (2)	−0.0016 (16)	0.0134 (17)	0.0038 (16)
C17	0.060 (2)	0.0309 (16)	0.070 (2)	−0.0027 (15)	0.0140 (19)	0.0133 (16)
C14	0.057 (2)	0.054 (2)	0.0386 (18)	−0.0039 (16)	0.0151 (16)	−0.0098 (15)
C23	0.065 (2)	0.045 (2)	0.090 (3)	−0.0036 (18)	0.043 (2)	−0.009 (2)
C25	0.045 (2)	0.052 (2)	0.095 (3)	0.0124 (17)	0.002 (2)	0.024 (2)
C24	0.048 (2)	0.052 (2)	0.121 (4)	0.0122 (18)	0.035 (3)	0.006 (2)

Geometric parameters (Å, º) top

Br1—C4	1.896 (3)	C21—C22	1.388 (5)
N1—C20	1.401 (4)	C13—C14	1.353 (5)
N1—C21	1.404 (4)	C13—H13	0.9300
N1—H55	0.78 (4)	C6—C7	1.352 (5)
C3—C4	1.396 (4)	C6—H6	0.9300
C3—C2	1.430 (4)	C7—H7	0.9300
C3—C12	1.432 (4)	C16—C17	1.383 (5)
C12—C11	1.405 (4)	C16—H16	0.9300
C12—C13	1.429 (4)	C26—C25	1.385 (5)
C11—C10	1.405 (4)	C26—H26	0.9300
C11—C15	1.497 (4)	C18—C17	1.366 (5)
C5—C4	1.400 (4)	C18—C19	1.375 (5)
C5—C6	1.428 (4)	C18—H18	0.9300
C5—C10	1.437 (4)	C1—C14	1.392 (5)
C10—C9	1.427 (4)	C1—H1	0.9300
C15—C20	1.386 (4)	C19—H19	0.9300
C15—C16	1.390 (4)	C22—C23	1.371 (5)
C9—C8	1.351 (5)	C22—H22	0.9300
C9—H9	0.9300	C17—H17	0.9300
C20—C19	1.395 (4)	C14—H14	0.9300
C2—C1	1.353 (4)	C23—C24	1.352 (6)
C2—H2	0.9300	C23—H23	0.9300
C8—C7	1.400 (5)	C25—C24	1.381 (6)
C8—H8	0.9300	C25—H25	0.9300
C21—C26	1.376 (5)	C24—H24	0.9300

C20—N1—C21	124.8 (3)	C12—C13—H13	119.6
C20—N1—H55	122 (3)	C7—C6—C5	121.0 (3)
C21—N1—H55	113 (3)	C7—C6—H6	119.5
C4—C3—C2	123.6 (3)	C5—C6—H6	119.5
C4—C3—C12	118.0 (2)	C6—C7—C8	120.8 (3)
C2—C3—C12	118.4 (3)	C6—C7—H7	119.6
C11—C12—C13	121.2 (3)	C8—C7—H7	119.6
C11—C12—C3	120.6 (3)	C17—C16—C15	121.5 (3)
C13—C12—C3	118.2 (3)	C17—C16—H16	119.2
C10—C11—C12	120.1 (2)	C15—C16—H16	119.2
C10—C11—C15	120.1 (2)	C21—C26—C25	119.7 (4)
C12—C11—C15	119.8 (2)	C21—C26—H26	120.2
C4—C5—C6	123.7 (3)	C25—C26—H26	120.2
C4—C5—C10	118.1 (2)	C17—C18—C19	120.2 (3)
C6—C5—C10	118.2 (3)	C17—C18—H18	119.9
C11—C10—C9	121.9 (3)	C19—C18—H18	119.9
C11—C10—C5	120.2 (2)	C2—C1—C14	121.1 (3)
C9—C10—C5	118.0 (3)	C2—C1—H1	119.5
C3—C4—C5	123.0 (3)	C14—C1—H1	119.5
C3—C4—Br1	118.7 (2)	C18—C19—C20	120.8 (3)
C5—C4—Br1	118.3 (2)	C18—C19—H19	119.6
C20—C15—C16	118.6 (3)	C20—C19—H19	119.6
C20—C15—C11	120.8 (3)	C23—C22—C21	120.1 (3)
C16—C15—C11	120.6 (3)	C23—C22—H22	119.9
C8—C9—C10	121.3 (3)	C21—C22—H22	119.9
C8—C9—H9	119.4	C18—C17—C16	119.4 (3)
C10—C9—H9	119.4	C18—C17—H17	120.3
C15—C20—C19	119.4 (3)	C16—C17—H17	120.3
C15—C20—N1	118.9 (3)	C13—C14—C1	120.9 (3)
C19—C20—N1	121.7 (3)	C13—C14—H14	119.5
C1—C2—C3	120.6 (3)	C1—C14—H14	119.5
C1—C2—H2	119.7	C24—C23—C22	121.3 (4)
C3—C2—H2	119.7	C24—C23—H23	119.3
C9—C8—C7	120.7 (3)	C22—C23—H23	119.3
C9—C8—H8	119.6	C24—C25—C26	120.7 (4)
C7—C8—H8	119.6	C24—C25—H25	119.7
C26—C21—C22	119.1 (3)	C26—C25—H25	119.7
C26—C21—N1	119.3 (3)	C23—C24—C25	119.1 (4)
C22—C21—N1	121.5 (3)	C23—C24—H24	120.4
C14—C13—C12	120.8 (3)	C25—C24—H24	120.4
C14—C13—H13	119.6

C4—C3—C12—C11	−0.2 (4)	C11—C15—C20—N1	−2.8 (5)
C2—C3—C12—C11	178.7 (3)	C21—N1—C20—C15	148.5 (3)
C4—C3—C12—C13	−179.9 (3)	C21—N1—C20—C19	−32.9 (5)
C2—C3—C12—C13	−1.0 (4)	C4—C3—C2—C1	178.5 (3)
C13—C12—C11—C10	178.9 (3)	C12—C3—C2—C1	−0.3 (4)
C3—C12—C11—C10	−0.8 (4)	C10—C9—C8—C7	−0.3 (5)
C13—C12—C11—C15	−1.1 (4)	C20—N1—C21—C26	144.7 (4)
C3—C12—C11—C15	179.2 (2)	C20—N1—C21—C22	−38.2 (5)
C12—C11—C10—C9	−179.0 (3)	C11—C12—C13—C14	−178.4 (3)
C15—C11—C10—C9	1.0 (4)	C3—C12—C13—C14	1.3 (5)
C12—C11—C10—C5	1.9 (4)	C4—C5—C6—C7	−179.1 (3)
C15—C11—C10—C5	−178.1 (2)	C10—C5—C6—C7	0.8 (4)
C4—C5—C10—C11	−2.0 (4)	C5—C6—C7—C8	−0.2 (5)
C6—C5—C10—C11	178.1 (3)	C9—C8—C7—C6	0.0 (5)
C4—C5—C10—C9	178.8 (2)	C20—C15—C16—C17	1.9 (5)
C6—C5—C10—C9	−1.0 (4)	C11—C15—C16—C17	−178.4 (3)
C2—C3—C4—C5	−178.8 (3)	C22—C21—C26—C25	−0.4 (5)
C12—C3—C4—C5	0.0 (4)	N1—C21—C26—C25	176.8 (3)
C2—C3—C4—Br1	1.3 (4)	C3—C2—C1—C14	1.6 (5)
C12—C3—C4—Br1	−179.9 (2)	C17—C18—C19—C20	1.0 (5)
C6—C5—C4—C3	−179.1 (3)	C15—C20—C19—C18	0.4 (5)
C10—C5—C4—C3	1.1 (4)	N1—C20—C19—C18	−178.3 (3)
C6—C5—C4—Br1	0.8 (4)	C26—C21—C22—C23	−0.5 (5)
C10—C5—C4—Br1	−179.03 (19)	N1—C21—C22—C23	−177.5 (3)
C10—C11—C15—C20	−86.9 (3)	C19—C18—C17—C16	−0.9 (6)
C12—C11—C15—C20	93.1 (3)	C15—C16—C17—C18	−0.5 (6)
C10—C11—C15—C16	93.3 (4)	C12—C13—C14—C1	−0.1 (5)
C12—C11—C15—C16	−86.7 (4)	C2—C1—C14—C13	−1.3 (5)
C11—C10—C9—C8	−178.3 (3)	C21—C22—C23—C24	1.1 (6)
C5—C10—C9—C8	0.8 (4)	C21—C26—C25—C24	0.6 (6)
C16—C15—C20—C19	−1.8 (5)	C22—C23—C24—C25	−0.9 (6)
C11—C15—C20—C19	178.5 (3)	C26—C25—C24—C23	0.0 (6)
C16—C15—C20—N1	176.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···Cg3ⁱ	0.93	2.77	3.598 (4)	148
C18—H18···Cg5ⁱ	0.93	2.85	3.661 (4)	146

Symmetry code: (i) x, y+1, z.

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