(2R)-2-Benzene­sulfonamido-2-phenyl­ethanoic acid

Arshad, M.N.; Tahir, M.N.; Khan, I.U.; Shafiq, M.; Ahmad, S.

doi:10.1107/S1600536809011611

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o940

doi:10.1107/S1600536809011611

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(2R)-2-Benzenesulfonamido-2-phenylethanoic acid

Muhammad Nadeem Arshad,^a M. Nawaz Tahir,^b ^* Islam Ullah Khan,^a Muhammad Shafiq ^a and Sarfraz Ahmad ^c

^aDepartment of Chemistry, Government College University, Lahore, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, and ^cPharmagen Ltd, Lahore 54000, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 27 March 2009; accepted 29 March 2009; online 2 April 2009)

In the title compound, C₁₄H₁₃NO₄S, the dihedral angle between the aromatic ring planes is 45.52 (18)°. In the crystal structure, intermolecular N—H⋯O and O—H⋯O hydrogen bonds lead to chains of molecules propagating in [100] in which the the ring motifs R₂¹(8), R₂²(8) and R₃³(11) are apparent. These polymeric chains are linked through C—H⋯O interactions.

Related literature

For related structures, see: Chaudhuri (1984 ); Shan & Huang (1999 ). For background, see: Arshad et al. (2008 ); Cama et al. (2003 ); Dankwardt et al. (2002 ); Zhi-jian et al. (2006 ). For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₃NO₄S
M_r = 291.31
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.6022 (5) Å
b = 12.5026 (9) Å
c = 19.7886 (15) Å
V = 1386.03 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.22 × 0.18 × 0.15 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.944, T_max = 0.966
8476 measured reflections
2818 independent reflections
1679 reflections with I > 2σ(I)
R_int = 0.050

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.091
S = 1.01
2818 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.28 e Å⁻³
Absolute structure: Flack (1983 ), 1092 Friedal Pairs
Flack parameter: 0.02 (10)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3ⁱ	0.86	2.55	3.155 (4)	128
O3—H3O⋯O4ⁱⁱ	0.82	1.83	2.646 (3)	176
C2—H2⋯O1ⁱⁱⁱ	0.93	2.56	3.340 (5)	142
C3—H3⋯O2^iv	0.93	2.54	3.225 (5)	131
C7—H7⋯O1ⁱⁱⁱ	0.98	2.55	3.432 (4)	150
Symmetry codes: (i) x+1, y, z; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ ; (iii) x-1, y, z; (iv) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011611/hb2938sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809011611/hb2938Isup2.hkl

checkCIF report

Comment top

Amino acid derived sulfonamides have been synthesized as ligands (Zhi-jian et al., 2006) which showed potent procollagen C-proteinase (PCP) inhibition (Dankwardt et al., 2002) and arginase inhibition (Cama et al., 2003). The title compound (I), (Fig 1), has been prepared as an intermediate for the synthesis of our ongoing studies of thiazine (Arshad et al., 2008) related heterocycles.

The crystal structure of (II) R-(-)-N-benzenesulfonylglutamic acid (Shan & Huang, 1999) and (III) N-Benzenesulfonyl-DL-alanine (Chaudhuri, 1984) have been published. These structures have a common group with (I) except the benzene ring of phenyl glycine.

The title compound has a chairal center at C7 with slightly distorted tetrahedral geometry with H7 at the apical position. The coordination around the S-atom is distorted tetrahedral. The molecules of the compound are stabilized due to strong intermolecular H-bonding (Table 1). Three ring motifs R₂¹(8), R₂²(8) and R₃³(11) (Bernstein et al., 1995) are formed due to two H-bonds of C—H···O type, H-bonding of types C—H···O and N—H···O, and two O—H···O and N—H···O, respectively (Fig 2). The ring motifs are connected to each other in such a way that a rod-shaped attachement of molecules exist along the a axis. These polymeric chains are linked through the remaing H-bonding of C—H···O type.

Related literature top

For related structures, see: Chaudhuri (1984); Shan & Huang (1999). For background, see: Arshad et al. (2008); Cama et al. (2003); Dankwardt et al. (2002); Zhi-jian et al. (2006). For graph-set notation, see: Bernstein et al. (1995).

Experimental top

Phenyl glycine (1 g, 6.6 mmol) was dissolved in distilled water (10 ml) in a round bottom flask (25 ml). The pH of the solution was maintained at 8–9 using 1M, Na₂CO₃ solution. Benzene sulfonyl chloride (1.16 g, 6.6 mmol) was then added to the solution and stirred at room temperature until all the benzene sulfonyl chloride was consumed. On completion of the reaction the pH was adjusted 1–2, using 1 N HCl. The precipitate obtained was filtered, washed with distilled water, dried and recrystalized in dichloromethane and methanol to yield colourless prisms of (I).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of (I) with displacement ellipsoids drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radius.
	Fig. 2. The partial packing of (I) showing that molecules form ring motifs through intermolecular H-bonding. The H-atoms not involved in H-bonding and the benzene ring of phenyl glycine are omited for clarity.

(2R)-2-Benzenesulfonamido-2-phenylethanoic acid top

Crystal data top

C₁₄H₁₃NO₄S	F(000) = 608
M_r = 291.31	D_x = 1.396 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2818 reflections
a = 5.6022 (5) Å	θ = 2.6–26.7°
b = 12.5026 (9) Å	µ = 0.25 mm⁻¹
c = 19.7886 (15) Å	T = 296 K
V = 1386.03 (19) Å³	Prism, colorless
Z = 4	0.22 × 0.18 × 0.15 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2818 independent reflections
Radiation source: fine-focus sealed tube	1679 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.050
Detector resolution: 7.80 pixels mm^-1	θ_max = 26.7°, θ_min = 2.6°
ω scans	h = −7→3
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −15→15
T_min = 0.944, T_max = 0.966	l = −25→25
8476 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.091	w = 1/[σ²(F_o²) + (0.0304P)²] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
2818 reflections	Δρ_max = 0.23 e Å⁻³
182 parameters	Δρ_min = −0.28 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1092 Friedal Pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (10)

Crystal data top

C₁₄H₁₃NO₄S	V = 1386.03 (19) Å³
M_r = 291.31	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.6022 (5) Å	µ = 0.25 mm⁻¹
b = 12.5026 (9) Å	T = 296 K
c = 19.7886 (15) Å	0.22 × 0.18 × 0.15 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2818 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1679 reflections with I > 2σ(I)
T_min = 0.944, T_max = 0.966	R_int = 0.050
8476 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.091	Δρ_max = 0.23 e Å⁻³
S = 1.01	Δρ_min = −0.28 e Å⁻³
2818 reflections	Absolute structure: Flack (1983), 1092 Friedal Pairs
182 parameters	Absolute structure parameter: 0.02 (10)
0 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
S1	0.8906 (2)	0.51683 (6)	0.15187 (4)	0.0387 (3)
O1	1.1438 (4)	0.50754 (15)	0.15986 (10)	0.0489 (9)
O2	0.7303 (5)	0.44742 (17)	0.18723 (11)	0.0554 (9)
O3	0.2940 (5)	0.62039 (15)	0.01637 (12)	0.0456 (10)
O4	0.6710 (5)	0.68015 (15)	0.01169 (12)	0.0496 (9)
N1	0.8409 (5)	0.49873 (16)	0.07161 (11)	0.0338 (9)
C1	0.8088 (7)	0.6505 (2)	0.17079 (15)	0.0363 (13)
C2	0.5942 (8)	0.6698 (3)	0.20125 (16)	0.0533 (14)
C3	0.5343 (9)	0.7746 (4)	0.21780 (18)	0.0723 (19)
C4	0.6886 (11)	0.8565 (3)	0.2012 (2)	0.075 (2)
C5	0.8993 (9)	0.8359 (3)	0.16954 (19)	0.0640 (18)
C6	0.9639 (7)	0.7318 (2)	0.15472 (16)	0.0521 (14)
C7	0.6001 (7)	0.49830 (19)	0.04431 (13)	0.0316 (12)
C8	0.5281 (8)	0.6104 (2)	0.02287 (14)	0.0340 (13)
C9	0.5829 (7)	0.4265 (2)	−0.01808 (14)	0.0318 (13)
C10	0.3966 (8)	0.3565 (2)	−0.02540 (17)	0.0507 (13)
C11	0.3774 (10)	0.2936 (3)	−0.0832 (2)	0.0690 (18)
C12	0.5456 (10)	0.3020 (3)	−0.1324 (2)	0.072 (2)
C13	0.7293 (9)	0.3721 (3)	−0.1256 (2)	0.080 (2)
C14	0.7496 (7)	0.4351 (3)	−0.06873 (18)	0.0583 (16)
H1	0.95974	0.48921	0.04478	0.0406*
H2	0.49001	0.61383	0.21076	0.0640*
H3	0.39147	0.78931	0.23985	0.0865*
H3O	0.26138	0.68249	0.00676	0.0547*
H4	0.64818	0.92669	0.21182	0.0899*
H5	1.00004	0.89197	0.15781	0.0768*
H6	1.10972	0.71706	0.13426	0.0624*
H7	0.48902	0.47247	0.07892	0.0379*
H10	0.28216	0.35094	0.00847	0.0608*
H11	0.25062	0.24614	−0.08804	0.0827*
H12	0.53489	0.25964	−0.17091	0.0872*
H13	0.84273	0.37763	−0.15968	0.0956*
H14	0.87550	0.48313	−0.06466	0.0702*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0371 (7)	0.0395 (4)	0.0395 (4)	0.0025 (5)	−0.0015 (5)	0.0072 (4)
O1	0.0308 (18)	0.0569 (13)	0.0590 (14)	0.0051 (14)	−0.0105 (13)	0.0060 (12)
O2	0.055 (2)	0.0573 (14)	0.0538 (14)	−0.0093 (13)	0.0066 (13)	0.0230 (11)
O3	0.037 (2)	0.0322 (13)	0.0677 (16)	0.0072 (13)	0.0039 (16)	0.0136 (12)
O4	0.048 (2)	0.0318 (11)	0.0690 (16)	−0.0128 (14)	−0.0048 (14)	0.0143 (10)
N1	0.030 (2)	0.0351 (13)	0.0364 (13)	0.0025 (15)	0.0059 (13)	−0.0056 (11)
C1	0.031 (3)	0.0481 (19)	0.0297 (18)	−0.0040 (18)	0.0001 (17)	−0.0046 (14)
C2	0.045 (3)	0.067 (2)	0.048 (2)	0.001 (3)	0.000 (2)	−0.0200 (17)
C3	0.049 (4)	0.096 (3)	0.072 (3)	0.016 (3)	−0.006 (2)	−0.039 (3)
C4	0.085 (5)	0.059 (3)	0.082 (3)	0.015 (3)	−0.011 (3)	−0.033 (2)
C5	0.070 (4)	0.046 (2)	0.076 (3)	−0.010 (2)	−0.004 (3)	−0.0124 (19)
C6	0.057 (3)	0.0494 (19)	0.050 (2)	0.001 (2)	0.009 (2)	−0.0060 (19)
C7	0.032 (3)	0.0251 (15)	0.0378 (16)	0.0002 (19)	0.0039 (17)	0.0037 (12)
C8	0.041 (3)	0.0298 (18)	0.0311 (17)	0.002 (2)	0.003 (2)	−0.0001 (14)
C9	0.030 (3)	0.0242 (14)	0.0412 (18)	0.0008 (17)	0.0001 (18)	0.0012 (13)
C10	0.057 (3)	0.0360 (17)	0.059 (2)	−0.006 (2)	0.003 (2)	−0.0045 (16)
C11	0.082 (4)	0.045 (2)	0.080 (3)	−0.014 (2)	−0.017 (3)	−0.012 (2)
C12	0.093 (5)	0.062 (3)	0.062 (3)	−0.005 (3)	−0.011 (3)	−0.027 (2)
C13	0.078 (5)	0.103 (3)	0.059 (3)	−0.017 (3)	0.020 (3)	−0.029 (2)
C14	0.059 (4)	0.068 (2)	0.048 (2)	−0.022 (2)	0.013 (2)	−0.017 (2)

Geometric parameters (Å, º) top

S1—O1	1.432 (3)	C9—C14	1.374 (5)
S1—O2	1.432 (3)	C9—C10	1.370 (5)
S1—N1	1.628 (2)	C10—C11	1.392 (5)
S1—C1	1.773 (3)	C11—C12	1.359 (7)
O3—C8	1.324 (5)	C12—C13	1.358 (7)
O4—C8	1.204 (4)	C13—C14	1.378 (5)
O3—H3O	0.8200	C2—H2	0.9300
N1—C7	1.453 (5)	C3—H3	0.9300
N1—H1	0.8600	C4—H4	0.9300
C1—C2	1.366 (6)	C5—H5	0.9300
C1—C6	1.375 (4)	C6—H6	0.9300
C2—C3	1.392 (6)	C7—H7	0.9800
C3—C4	1.380 (7)	C10—H10	0.9300
C4—C5	1.361 (7)	C11—H11	0.9300
C5—C6	1.382 (5)	C12—H12	0.9300
C7—C8	1.519 (4)	C13—H13	0.9300
C7—C9	1.530 (4)	C14—H14	0.9300

O1—S1—O2	121.22 (14)	C10—C11—C12	119.4 (4)
O1—S1—N1	105.42 (14)	C11—C12—C13	120.3 (4)
O1—S1—C1	108.01 (15)	C12—C13—C14	120.8 (4)
O2—S1—N1	106.58 (14)	C9—C14—C13	119.7 (4)
O2—S1—C1	107.82 (16)	C1—C2—H2	121.00
N1—S1—C1	107.03 (13)	C3—C2—H2	121.00
C8—O3—H3O	109.00	C2—C3—H3	120.00
S1—N1—C7	121.5 (2)	C4—C3—H3	120.00
S1—N1—H1	119.00	C3—C4—H4	120.00
C7—N1—H1	119.00	C5—C4—H4	120.00
C2—C1—C6	121.9 (3)	C4—C5—H5	120.00
S1—C1—C2	119.2 (3)	C6—C5—H5	120.00
S1—C1—C6	119.0 (3)	C1—C6—H6	121.00
C1—C2—C3	118.8 (4)	C5—C6—H6	121.00
C2—C3—C4	119.5 (4)	N1—C7—H7	109.00
C3—C4—C5	120.8 (4)	C8—C7—H7	109.00
C4—C5—C6	120.2 (4)	C9—C7—H7	109.00
C1—C6—C5	118.8 (4)	C9—C10—H10	120.00
C8—C7—C9	107.4 (2)	C11—C10—H10	120.00
N1—C7—C9	111.2 (3)	C10—C11—H11	120.00
N1—C7—C8	110.3 (3)	C12—C11—H11	120.00
O3—C8—O4	124.9 (3)	C11—C12—H12	120.00
O3—C8—C7	112.2 (3)	C13—C12—H12	120.00
O4—C8—C7	122.9 (4)	C12—C13—H13	120.00
C7—C9—C10	120.6 (3)	C14—C13—H13	120.00
C7—C9—C14	120.0 (3)	C9—C14—H14	120.00
C10—C9—C14	119.4 (3)	C13—C14—H14	120.00
C9—C10—C11	120.4 (4)

O1—S1—N1—C7	177.57 (18)	C4—C5—C6—C1	1.8 (6)
O2—S1—N1—C7	47.6 (2)	N1—C7—C8—O3	−161.7 (2)
C1—S1—N1—C7	−67.6 (2)	N1—C7—C8—O4	20.1 (4)
O1—S1—C1—C2	−145.8 (3)	C9—C7—C8—O3	77.0 (3)
O1—S1—C1—C6	33.9 (3)	C9—C7—C8—O4	−101.2 (4)
O2—S1—C1—C2	−13.2 (3)	N1—C7—C9—C10	134.8 (3)
O2—S1—C1—C6	166.5 (3)	N1—C7—C9—C14	−48.0 (4)
N1—S1—C1—C2	101.2 (3)	C8—C7—C9—C10	−104.5 (3)
N1—S1—C1—C6	−79.2 (3)	C8—C7—C9—C14	72.7 (4)
S1—N1—C7—C8	90.6 (2)	C7—C9—C10—C11	178.0 (3)
S1—N1—C7—C9	−150.35 (18)	C14—C9—C10—C11	0.8 (5)
S1—C1—C2—C3	178.1 (3)	C7—C9—C14—C13	−178.3 (3)
C6—C1—C2—C3	−1.5 (5)	C10—C9—C14—C13	−1.0 (5)
S1—C1—C6—C5	180.0 (3)	C9—C10—C11—C12	0.1 (6)
C2—C1—C6—C5	−0.4 (5)	C10—C11—C12—C13	−0.8 (7)
C1—C2—C3—C4	2.1 (6)	C11—C12—C13—C14	0.5 (7)
C2—C3—C4—C5	−0.7 (6)	C12—C13—C14—C9	0.4 (6)
C3—C4—C5—C6	−1.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.55	3.155 (4)	128
O3—H3O···O4ⁱⁱ	0.82	1.83	2.646 (3)	176
C2—H2···O1ⁱⁱⁱ	0.93	2.56	3.340 (5)	142
C3—H3···O2^iv	0.93	2.54	3.225 (5)	131
C7—H7···O1ⁱⁱⁱ	0.98	2.55	3.432 (4)	150

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+3/2, −z; (iii) x−1, y, z; (iv) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₄S
M_r	291.31
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	5.6022 (5), 12.5026 (9), 19.7886 (15)
V (Å³)	1386.03 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.22 × 0.18 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.944, 0.966
No. of measured, independent and observed [I > 2σ(I)] reflections	8476, 2818, 1679
R_int	0.050
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.091, 1.01
No. of reflections	2818
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.28
Absolute structure	Flack (1983), 1092 Friedal Pairs
Absolute structure parameter	0.02 (10)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.55	3.155 (4)	128
O3—H3O···O4ⁱⁱ	0.82	1.83	2.646 (3)	176
C2—H2···O1ⁱⁱⁱ	0.93	2.56	3.340 (5)	142
C3—H3···O2^iv	0.93	2.54	3.225 (5)	131
C7—H7···O1ⁱⁱⁱ	0.98	2.55	3.432 (4)	150

Symmetry codes: (i) x+1, y, z; (ii) x−1/2, −y+3/2, −z; (iii) x−1, y, z; (iv) −x+1, y+1/2, −z+1/2.

Acknowledgements

MNA greatfully acknowledges the Higher Education Commission, Islamabad, Pakistan, for providing him with a Scholaship under the Indigenous PhD Program (PIN 042–120607-PS2-183).

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