2,4-Dichloro-N-(2-chloro­phen­yl)benzene­sulfonamide

Gowda, B.T.; Foro, S.; Nirmala, P.G.; Fuess, H.

doi:10.1107/S1600536810021306

organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1641

doi:10.1107/S1600536810021306

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2,4-Dichloro-N-(2-chlorophenyl)benzenesulfonamide

B. Thimme Gowda,^a ^* Sabine Foro,^b P. G. Nirmala ^a and Hartmut Fuess ^b

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, and ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 2 June 2010; accepted 3 June 2010; online 16 June 2010)

In the title compound, C₁₂H₈Cl₃NO₂S, the conformation of the N—H bond in the C—SO₂—NH—C segment is syn to the ortho-Cl in the aniline ring. The dihedral angle between the two benzene rings is 74.3 (1)°. An intramolecular N—H⋯Cl hydrogen bond occurs. In the crystal, pairs of N—H⋯O hydrogen bonds link the molecules into dimers.

Related literature

For the preparation of the title compound, see: Savitha & Gowda (2006 ). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2010a ,b ); Nirmala et al. (2010 ). For related structures, see: Gelbrich et al. (2007 ); Perlovich et al. (2006 ).

Experimental

Crystal data

C₁₂H₈Cl₃NO₂S
M_r = 336.60
Orthorhombic, P b c n
a = 10.5639 (8) Å
b = 16.279 (1) Å
c = 16.693 (1) Å
V = 2870.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.78 mm⁻¹
T = 299 K
0.30 × 0.24 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.800, T_max = 0.847
8054 measured reflections
2938 independent reflections
2054 reflections with I > 2σ(I)
R_int = 0.019

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.107
S = 1.01
2938 reflections
175 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.86 (1)	2.23 (2)	3.007 (3)	152 (2)
N1—H1N⋯Cl3	0.86 (1)	2.57 (3)	2.975 (2)	110 (2)
Symmetry code: (i) $[-x, y, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810021306/bq2220sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810021306/bq2220Isup2.hkl

checkCIF report

Comment top

As a part of studying the substituent effects on the structures of N-(aryl)arylsulfonamides (Gowda et al. , 2010a,b; Nirmala et al., 2010), the structure of 2,4-dichloro-N-(2-chlorophenyl)-benzenesulfonamide (I) has been determined (Fig. 1). The conformation of the N—H bond in the C—SO₂—NH—C segment is syn to the ortho-Cl in the aniline ring (Fig. 1), contrary to the anti conformation observed between the N—H bond and meta-Cl in the aniline ring of 2,4-dichloro-N-(3-chlorophenyl)-benzenesulfonamide (II) (Gowda et al., 2010a).

The molecule is twisted at the S atom with the C1—SO₂—NH—C7 torsion angle of 54.5 (3)°, compared to the values of 62.3 (2)° in (II), 67.8 (2)° in 2,4-dichloro-N-(4-chlorophenyl)benzenesulfonamide (III)(Nirmala et al., 2010), 55.1 (3)° (molecule 1) and -48.3 (3)° (molecule 2) in 2,4-dichloro-N-(phenyl)-benzenesulfonamide (IV) (Gowda et al., 2010b). The sulfonyl benzene and the aniline benzene rings in (I) are tilted relative to each other by 74.3 (1)°, compared to the values of 69.3 (1)° in (II), 65.0 (1)° in (III), 80.5 (2)° in the molecule 1 and 64.9 (1)° in molecule 2 of (IV).

The other bond parameters in (I) are similar to those observed in (II), (III), (IV) and other aryl sulfonamides (Perlovich et al., 2006; Gelbrich et al., 2007).

In the crystal structure, the pairs of intermolecular N–H···O hydrogen bonds (Table 1) link the molecules via dimers into infinite sequences running parallel to the c-axis. Part of the crystal structure is shown in Fig. 2.

Related literature top

For the preparation of the title compound, see: Savitha & Gowda (2006). For our studies of the effect of substituents on the structures of N-(aryl)arylsulfonamides, see: Gowda et al. (2010a,b); Nirmala et al. (2010). For related structures, see: Gelbrich et al. (2007); Perlovich et al. (2006).

Experimental top

The solution of 1,3-dichlorobenzene (10 cc) in chloroform (40 cc) was treated dropwise with chlorosulfonic acid (25 cc) at 0 ° C. After the initial evolution of hydrogen chloride subsided, the reaction mixture was brought to room temperature and poured into crushed ice in a beaker. The chloroform layer was separated, washed with cold water and allowed to evaporate slowly. The residual 2,4-dichlorobenzenesulfonylchloride was treated with 2-chloroaniline in the stoichiometric ratio and boiled for ten minutes. The reaction mixture was then cooled to room temperature and added to ice cold water (100 cc). The resultant solid 2,4-dichloro-N-(2-chlorophenyl)benzenesulfonamide was filtered under suction and washed thoroughly with cold water. It was then recrystallized to constant melting point from dilute ethanol. The purity of the compound was checked and characterized by recording its infrared and NMR spectra (Savitha & Gowda, 2006). Prism like colorless single crystals used in X-ray diffraction studies were grown in ethanolic solution by slow evaporation at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I), showing the atom labelling scheme and displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.

2,4-Dichloro-N-(2-chlorophenyl)benzenesulfonamide top

Crystal data top

C₁₂H₈Cl₃NO₂S	F(000) = 1360
M_r = 336.60	D_x = 1.558 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 2957 reflections
a = 10.5639 (8) Å	θ = 2.5–27.8°
b = 16.279 (1) Å	µ = 0.78 mm⁻¹
c = 16.693 (1) Å	T = 299 K
V = 2870.7 (3) Å³	Prism, colourless
Z = 8	0.30 × 0.24 × 0.22 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2938 independent reflections
Radiation source: fine-focus sealed tube	2054 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.019
Rotation method data acquisition using ω and phi scans	θ_max = 26.4°, θ_min = 2.5°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −9→13
T_min = 0.800, T_max = 0.847	k = −14→20
8054 measured reflections	l = −11→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0458P)² + 1.5152P] where P = (F_o² + 2F_c²)/3
2938 reflections	(Δ/σ)_max < 0.001
175 parameters	Δρ_max = 0.36 e Å⁻³
1 restraint	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₁₂H₈Cl₃NO₂S	V = 2870.7 (3) Å³
M_r = 336.60	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 10.5639 (8) Å	µ = 0.78 mm⁻¹
b = 16.279 (1) Å	T = 299 K
c = 16.693 (1) Å	0.30 × 0.24 × 0.22 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2938 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2054 reflections with I > 2σ(I)
T_min = 0.800, T_max = 0.847	R_int = 0.019
8054 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	1 restraint
wR(F²) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.36 e Å⁻³
2938 reflections	Δρ_min = −0.35 e Å⁻³
175 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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	0.3134 (2)	0.61639 (15)	0.32900 (15)	0.0497 (6)
C2	0.2866 (3)	0.53340 (17)	0.31598 (16)	0.0579 (7)
C3	0.3728 (3)	0.47403 (19)	0.3366 (2)	0.0753 (9)
H3	0.3545	0.4188	0.3282	0.090*
C4	0.4862 (3)	0.4967 (2)	0.3697 (2)	0.0850 (10)
C5	0.5150 (3)	0.5775 (2)	0.3827 (2)	0.0919 (11)
H5	0.5923	0.5920	0.4052	0.110*
C6	0.4285 (3)	0.6371 (2)	0.36218 (19)	0.0713 (8)
H6	0.4480	0.6921	0.3708	0.086*
C7	0.0989 (2)	0.68618 (15)	0.45102 (14)	0.0477 (6)
C8	0.0161 (2)	0.63852 (15)	0.49537 (15)	0.0509 (6)
C9	0.0238 (3)	0.63637 (17)	0.57821 (16)	0.0664 (8)
H9	−0.0334	0.6050	0.6076	0.080*
C10	0.1164 (3)	0.68083 (19)	0.61698 (17)	0.0730 (9)
H10	0.1232	0.6786	0.6725	0.088*
C11	0.1978 (3)	0.7281 (2)	0.57371 (17)	0.0703 (8)
H11	0.2600	0.7581	0.6000	0.084*
C12	0.1892 (3)	0.73195 (18)	0.49182 (16)	0.0629 (7)
H12	0.2444	0.7655	0.4633	0.075*
N1	0.08883 (19)	0.68827 (15)	0.36630 (12)	0.0542 (6)
H1N	0.0212 (16)	0.6693 (15)	0.3452 (15)	0.065*
O1	0.15449 (18)	0.68354 (12)	0.22707 (9)	0.0648 (5)
O2	0.27286 (18)	0.77149 (11)	0.32041 (12)	0.0675 (5)
Cl1	0.14598 (8)	0.50245 (5)	0.27304 (6)	0.0914 (3)
Cl2	0.59587 (12)	0.42218 (8)	0.39456 (10)	0.1453 (5)
Cl3	−0.09873 (7)	0.58020 (5)	0.44734 (5)	0.0691 (2)
S1	0.20683 (6)	0.69660 (4)	0.30490 (4)	0.05119 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0463 (14)	0.0562 (15)	0.0466 (14)	−0.0060 (12)	0.0030 (11)	0.0018 (12)
C2	0.0561 (16)	0.0593 (16)	0.0584 (16)	−0.0085 (14)	0.0062 (13)	−0.0016 (13)
C3	0.082 (2)	0.0563 (17)	0.087 (2)	0.0018 (17)	0.0103 (18)	0.0005 (17)
C4	0.075 (2)	0.083 (2)	0.097 (3)	0.024 (2)	−0.0010 (19)	0.006 (2)
C5	0.0572 (19)	0.099 (3)	0.119 (3)	0.0074 (19)	−0.0242 (18)	−0.003 (2)
C6	0.0537 (17)	0.0678 (19)	0.092 (2)	−0.0065 (15)	−0.0125 (16)	−0.0029 (17)
C7	0.0517 (14)	0.0510 (14)	0.0403 (13)	0.0108 (12)	−0.0058 (11)	−0.0019 (11)
C8	0.0630 (16)	0.0433 (13)	0.0463 (14)	0.0131 (12)	−0.0027 (12)	0.0000 (12)
C9	0.093 (2)	0.0583 (17)	0.0482 (16)	0.0183 (17)	0.0063 (15)	0.0079 (14)
C10	0.110 (3)	0.069 (2)	0.0401 (15)	0.0277 (19)	−0.0159 (16)	−0.0087 (15)
C11	0.086 (2)	0.0712 (19)	0.0535 (17)	0.0103 (17)	−0.0189 (15)	−0.0123 (15)
C12	0.0659 (17)	0.0709 (19)	0.0518 (16)	−0.0033 (15)	−0.0088 (13)	−0.0053 (14)
N1	0.0456 (12)	0.0765 (16)	0.0404 (11)	−0.0022 (11)	−0.0071 (9)	−0.0013 (11)
O1	0.0674 (11)	0.0888 (14)	0.0382 (9)	−0.0078 (11)	−0.0027 (8)	0.0105 (9)
O2	0.0745 (13)	0.0518 (10)	0.0763 (13)	−0.0140 (10)	−0.0064 (10)	0.0104 (10)
Cl1	0.0830 (6)	0.0772 (5)	0.1140 (7)	−0.0306 (5)	−0.0171 (5)	−0.0062 (5)
Cl2	0.1218 (9)	0.1269 (10)	0.1873 (13)	0.0642 (8)	−0.0140 (9)	0.0199 (9)
Cl3	0.0743 (5)	0.0665 (5)	0.0665 (5)	−0.0100 (4)	−0.0044 (4)	0.0089 (4)
S1	0.0528 (4)	0.0574 (4)	0.0434 (3)	−0.0060 (3)	−0.0025 (3)	0.0086 (3)

Geometric parameters (Å, º) top

C1—C6	1.379 (3)	C7—N1	1.419 (3)
C1—C2	1.397 (3)	C8—C9	1.386 (4)
C1—S1	1.770 (3)	C8—Cl3	1.737 (3)
C2—C3	1.372 (4)	C9—C10	1.378 (4)
C2—Cl1	1.725 (3)	C9—H9	0.9300
C3—C4	1.369 (5)	C10—C11	1.361 (4)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.367 (5)	C11—C12	1.372 (4)
C4—Cl2	1.728 (3)	C11—H11	0.9300
C5—C6	1.377 (4)	C12—H12	0.9300
C5—H5	0.9300	N1—S1	1.620 (2)
C6—H6	0.9300	N1—H1N	0.855 (10)
C7—C8	1.383 (4)	O1—S1	1.4279 (17)
C7—C12	1.389 (3)	O2—S1	1.4282 (18)

C6—C1—C2	118.5 (3)	C9—C8—Cl3	119.2 (2)
C6—C1—S1	118.1 (2)	C10—C9—C8	119.8 (3)
C2—C1—S1	123.3 (2)	C10—C9—H9	120.1
C3—C2—C1	120.5 (3)	C8—C9—H9	120.1
C3—C2—Cl1	118.1 (2)	C11—C10—C9	119.7 (3)
C1—C2—Cl1	121.4 (2)	C11—C10—H10	120.1
C4—C3—C2	119.5 (3)	C9—C10—H10	120.1
C4—C3—H3	120.3	C10—C11—C12	120.9 (3)
C2—C3—H3	120.3	C10—C11—H11	119.6
C5—C4—C3	121.2 (3)	C12—C11—H11	119.6
C5—C4—Cl2	119.2 (3)	C11—C12—C7	120.6 (3)
C3—C4—Cl2	119.6 (3)	C11—C12—H12	119.7
C4—C5—C6	119.5 (3)	C7—C12—H12	119.7
C4—C5—H5	120.3	C7—N1—S1	125.13 (17)
C6—C5—H5	120.3	C7—N1—H1N	117.7 (19)
C5—C6—C1	120.8 (3)	S1—N1—H1N	114.3 (19)
C5—C6—H6	119.6	O1—S1—O2	118.76 (12)
C1—C6—H6	119.6	O1—S1—N1	105.39 (11)
C8—C7—C12	118.2 (2)	O2—S1—N1	109.43 (12)
C8—C7—N1	120.0 (2)	O1—S1—C1	110.08 (12)
C12—C7—N1	121.8 (2)	O2—S1—C1	106.14 (12)
C7—C8—C9	120.7 (3)	N1—S1—C1	106.48 (12)
C7—C8—Cl3	120.06 (19)

C6—C1—C2—C3	0.7 (4)	Cl3—C8—C9—C10	178.5 (2)
S1—C1—C2—C3	−179.4 (2)	C8—C9—C10—C11	1.5 (4)
C6—C1—C2—Cl1	−178.8 (2)	C9—C10—C11—C12	−0.2 (5)
S1—C1—C2—Cl1	1.1 (3)	C10—C11—C12—C7	−1.5 (4)
C1—C2—C3—C4	−0.4 (5)	C8—C7—C12—C11	1.7 (4)
Cl1—C2—C3—C4	179.0 (3)	N1—C7—C12—C11	−179.2 (3)
C2—C3—C4—C5	0.1 (5)	C8—C7—N1—S1	−145.6 (2)
C2—C3—C4—Cl2	−179.1 (2)	C12—C7—N1—S1	35.3 (4)
C3—C4—C5—C6	0.0 (6)	C7—N1—S1—O1	171.4 (2)
Cl2—C4—C5—C6	179.3 (3)	C7—N1—S1—O2	−59.8 (2)
C4—C5—C6—C1	0.2 (5)	C7—N1—S1—C1	54.5 (2)
C2—C1—C6—C5	−0.5 (4)	C6—C1—S1—O1	134.6 (2)
S1—C1—C6—C5	179.6 (3)	C2—C1—S1—O1	−45.3 (2)
C12—C7—C8—C9	−0.3 (4)	C6—C1—S1—O2	4.9 (2)
N1—C7—C8—C9	−179.4 (2)	C2—C1—S1—O2	−175.0 (2)
C12—C7—C8—Cl3	179.94 (19)	C6—C1—S1—N1	−111.6 (2)
N1—C7—C8—Cl3	0.8 (3)	C2—C1—S1—N1	68.5 (2)
C7—C8—C9—C10	−1.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.86 (1)	2.23 (2)	3.007 (3)	152 (2)
N1—H1N···Cl3	0.86 (1)	2.57 (3)	2.975 (2)	110 (2)

Symmetry code: (i) −x, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₈Cl₃NO₂S
M_r	336.60
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	299
a, b, c (Å)	10.5639 (8), 16.279 (1), 16.693 (1)
V (Å³)	2870.7 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.78
Crystal size (mm)	0.30 × 0.24 × 0.22

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.800, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	8054, 2938, 2054
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.107, 1.01
No. of reflections	2938
No. of parameters	175
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.35

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.855 (10)	2.225 (16)	3.007 (3)	152 (2)
N1—H1N···Cl3	0.855 (10)	2.57 (3)	2.975 (2)	110 (2)

Symmetry code: (i) −x, y, −z+1/2.

References

Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010a). Acta Cryst. E66, o1552. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010b). Private communication (refcode CCDC 740692). CCDC, Union Road, Cambridge, England. Google Scholar
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Volume 66| Part 7| July 2010| Page o1641

doi:10.1107/S1600536810021306

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