organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 7| July 2015| Pages o466-o467

Crystal structure of 2-{[2-meth­­oxy-5-(tri­fluoro­meth­yl)phen­yl]imino­methyl}-4-nitro­phenol

CROSSMARK_Color_square_no_text.svg

aYeşilyurt Demir Celik Higher Vocational School, Ondokuz Mayıs University, TR-55330 Tekkeköy-Samsun, Turkey, bDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Samsun, Turkey, and cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, TR-55139 Samsun, Turkey
*Correspondence e-mail: nevzatk@omu.edu.tr

Edited by H. Ishida, Okayama University, Japan (Received 16 April 2015; accepted 25 May 2015; online 13 June 2015)

In the title compound, C15H11F3N2O4, the N=C bond of the central imine group adopts an E conformation. The dihedral angle between two benzene rings is 6.2 (2)°. There is an intra­molecular bifurcated O—H⋯(N,O) hydrogen bond with S(6) and S(9) ring motifs. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into a helical chain along the 31 screw axis parallel to c. The –CF3 group shows rotational disorder over two sites, with occupancies of 0.39 (2) and 0.61 (2).

1. Related literature

For photochromic, thermochromic and biological applications of related Schiff base compounds, see: Hadjoudis et al. (1987[Hadjoudis, E., Vittorakis, M. & Moustakali-Mavridis, I. (1987). Tetrahedron, 43, 1345-1360.]); Santos et al. (2001[Santos, M. L. P., Bagatin, I. A., Pereira, E. M. & Ferreira, A. M. D. C. (2001). J. Chem. Soc. Dalton Trans. pp. 838-844.]); Tarafder et al. (2002[Tarafder, M. T. H., Chew, K., Crouse, K. A., Ali, A. M., Yamin, B. M. & Fun, H.-K. (2002). Polyhedron, 21, 2683-2690.]). For related structures, see: Faridbod et al. (2008[Faridbod, F., Ganjali, M. R., Dinarvand, R., Norouzi, P. & Riahi, S. (2008). Sensors, 8, 1645-1703.]); Karadayı et al. (2003[Karadayı, N., Gözüyeşil, S., Güzel, B., Kazak, C. & Büyükgüngör, O. (2003). Acta Cryst. E59, o851-o853.], 2006[Karadayı, N., Albayrak, Ç., Odabaşoğlu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1699-o1701.], 2013[Karadayı, N., Köysal, Y., Şahin, S., Coşkun, E. & Büyükgüngör, O. (2013). Acta Cryst. E69, o889.]); Raja et al. (2008[Raja, K. K., Bilal, I. M., Thambidurai, S., Rajagopal, G. & SubbiahPandi, A. (2008). Acta Cryst. E64, o2265.]).

[Scheme 1]

2. Experimental

2.1. Crystal data

  • C15H11F3N2O4

  • Mr = 340.26

  • Trigonal, [R \overline 3]

  • a = 33.0327 (16) Å

  • c = 7.1523 (3) Å

  • V = 6758.7 (5) Å3

  • Z = 18

  • Mo Kα radiation

  • μ = 0.13 mm−1

  • T = 296 K

  • 0.67 × 0.25 × 0.04 mm

2.2. Data collection

  • Stoe IPDS 2 diffractometer

  • Absorption correction: integration (X-RED32; Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]) Tmin = 0.951, Tmax = 0.994

  • 16356 measured reflections

  • 2958 independent reflections

  • 1380 reflections with I > 2σ(I)

  • Rint = 0.140

2.3. Refinement

  • R[F2 > 2σ(F2)] = 0.084

  • wR(F2) = 0.126

  • S = 1.07

  • 2958 reflections

  • 246 parameters

  • H-atom parameters constrained

  • Δρmax = 0.15 e Å−3

  • Δρmin = −0.19 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯N1 0.82 1.84 2.571 (4) 148
O1—H1⋯O4 0.82 2.76 3.468 (4) 146
C7—H7⋯O2i 0.93 2.55 3.476 (7) 176
C9—H9⋯O2i 0.93 2.46 3.378 (6) 169
Symmetry code: (i) [-y+{\script{4\over 3}}, x-y-{\script{1\over 3}}, z-{\script{1\over 3}}].

Data collection: X-AREA (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002[Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.]); 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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).

Supporting information


Comment top

Schiff base compounds can be classified by their photochromic and thermochromic characteristics (Hadjoudis et al., 1987). Schiff bases are potentially biologically active compounds and the antifungal, anticancer, anticonvulsant, diuretic and cytotoxic activities have been reported. For the development of bacteriostatic activity, it is believed that the presence of a nitro group in the p-position is an important condition (Tarafder et al., 2002; Santos et al., 2001). In this study we report the structure of the title compound (I).

The N1C7 bond length is 1.295 (5) Å, approximately equal to previously reported CN bond lengths (Karadayı et al., 2003; Faridbod et al., 2008; Karadayı et al., 2013). The geometric parameters in (I) are comparable with the similar reported structures (Raja et al., 2008; Karadayı et al., 2006). The dihedral angle between the aromatic rings (C1–C6) and (C8–C13) is 6.2 (2)°. The CF3 group showed rotational disorder. The site occupancy factors are 0.39 (2) and 0.61 (2) for F1A–F3A and F1B–F3B, respectively. An intramolecular bifurcated O—H···(N, O) hydrogen bond is observed (Table 1 and Fig. 1).

Related literature top

For photochromic, thermochromic and biological applications of related Schiff base compounds, see: Hadjoudis et al. (1987); Santos et al. (2001); Tarafder et al. (2002). For related structures, see: Faridbod et al. (2008); Karadayı et al. (2003, 2006, 2013); Raja et al. (2008).

Experimental top

The title compound was prepared by refluxing a mixture of a solution containing 2-hydroxy-5-nitrobenzaldehyde (0.014 g, 0.082 mmol) and a solution containing 2-methoxy-5-(trifluoromethyl)aniline (0,016 g, 0.082 mmol) in 20 ml ethanol. The reaction mixture was stirred for 1 h under reflux. Single crystals suitable for X-ray analysis were obtained from an ethanol solution by slow evaporation (yield 54%, m.p. 475–477 K).

Refinement top

All H atoms were placed in calculated positions and refined using a riding model, with C—H = 0.93 or 0.96 Å and O—H = 0.82 Å. The isotropic displacement parameters of the H atoms were fixed at 1.2Ueq(C) or 1.5Ueq(O, Cmethyl). The CF3 group showed rotational disorder. The site occupancy factors are 0.39 (2) and 0.61 (2) for F1A–F3A and F1B–F3B, respectively.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); 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, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top
[Figure 1] Fig. 1. An ORTEP drawing of the title compound showing the atomic numbering scheme. Displacement ellipsoids of non-H atoms are shown at the 20% probability level. Hydrogen bonds are indicated by dashed lines.
2-{[2-Methoxy-5-(trifluoromethyl)phenyl]iminomethyl}-4-nitrophenol top
Crystal data top
C15H11F3N2O4Dx = 1.505 Mg m3
Mr = 340.26Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 10608 reflections
Hall symbol: -R 3θ = 2.1–28.0°
a = 33.0327 (16) ŵ = 0.13 mm1
c = 7.1523 (3) ÅT = 296 K
V = 6758.7 (5) Å3Needle, light brown
Z = 180.67 × 0.25 × 0.04 mm
F(000) = 3132
Data collection top
Stoe IPDS 2
diffractometer
2958 independent reflections
Radiation source: fine-focus sealed tube1380 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.140
ω scansθmax = 26.0°, θmin = 2.1°
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
h = 4040
Tmin = 0.951, Tmax = 0.994k = 3940
16356 measured reflectionsl = 88
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)] = 0.084Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0292P)2]
where P = (Fo2 + 2Fc2)/3
2958 reflections(Δ/σ)max = 0.001
246 parametersΔρmax = 0.15 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C15H11F3N2O4Z = 18
Mr = 340.26Mo Kα radiation
Trigonal, R3µ = 0.13 mm1
a = 33.0327 (16) ÅT = 296 K
c = 7.1523 (3) Å0.67 × 0.25 × 0.04 mm
V = 6758.7 (5) Å3
Data collection top
Stoe IPDS 2
diffractometer
2958 independent reflections
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
1380 reflections with I > 2σ(I)
Tmin = 0.951, Tmax = 0.994Rint = 0.140
16356 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0840 restraints
wR(F2) = 0.126H-atom parameters constrained
S = 1.07Δρmax = 0.15 e Å3
2958 reflectionsΔρmin = 0.19 e Å3
246 parameters
Special details top

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
xyzUiso*/UeqOcc. (<1)
O40.76299 (10)0.04667 (9)0.2585 (4)0.0569 (8)
O10.76808 (9)0.14868 (10)0.4121 (5)0.0647 (9)
H10.77980.13300.37980.097*
N10.83251 (11)0.12822 (11)0.3519 (4)0.0443 (8)
N20.90475 (14)0.32508 (12)0.6373 (5)0.0538 (9)
C70.86313 (14)0.17045 (14)0.4002 (5)0.0473 (10)
H70.89470.17970.39690.057*
C10.84911 (13)0.20297 (13)0.4583 (5)0.0417 (10)
O30.94606 (11)0.33571 (11)0.6341 (5)0.0724 (10)
C60.80087 (14)0.18987 (14)0.4640 (6)0.0488 (11)
C40.82253 (15)0.26645 (15)0.5825 (6)0.0529 (11)
H40.81410.28790.62410.063*
C20.88280 (14)0.24797 (13)0.5163 (6)0.0452 (10)
H20.91430.25680.51310.054*
C30.86965 (13)0.27894 (13)0.5775 (6)0.0429 (10)
C130.80545 (15)0.04950 (14)0.2514 (6)0.0463 (10)
C100.89519 (15)0.06269 (15)0.2580 (6)0.0549 (12)
O20.89212 (12)0.35192 (11)0.6969 (5)0.0788 (10)
C110.85770 (17)0.01995 (16)0.2083 (6)0.0614 (13)
H110.86270.00450.17720.074*
C50.78900 (15)0.22311 (14)0.5269 (6)0.0544 (11)
H50.75780.21520.53030.065*
C90.88791 (15)0.09902 (15)0.3038 (6)0.0532 (11)
H90.91320.12780.33730.064*
C80.84359 (13)0.09318 (13)0.3005 (5)0.0424 (10)
C120.81262 (16)0.01297 (14)0.2039 (6)0.0568 (12)
H120.78760.01590.16950.068*
C150.72262 (15)0.00229 (14)0.2147 (6)0.0630 (13)
H15A0.69500.00480.22400.094*
H15B0.72050.02090.30110.094*
H15C0.72540.00660.08970.094*
C140.9427 (2)0.0689 (2)0.2677 (12)0.0853 (18)
F1A0.9456 (8)0.0369 (9)0.340 (5)0.142 (14)0.39 (2)
F2A0.9748 (7)0.1072 (7)0.317 (7)0.158 (16)0.39 (2)
F3A0.9570 (6)0.0665 (12)0.074 (2)0.152 (9)0.39 (2)
F1B0.9474 (5)0.0345 (4)0.221 (3)0.136 (9)0.61 (2)
F2B0.9590 (5)0.0783 (9)0.4489 (18)0.156 (7)0.61 (2)
F3B0.9727 (4)0.1064 (6)0.181 (2)0.128 (7)0.61 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O40.0435 (17)0.0424 (17)0.077 (2)0.0155 (15)0.0007 (15)0.0058 (15)
O10.0437 (17)0.048 (2)0.097 (3)0.0190 (16)0.0001 (17)0.0140 (17)
N10.045 (2)0.0307 (18)0.050 (2)0.0140 (17)0.0002 (17)0.0023 (15)
N20.057 (3)0.040 (2)0.059 (2)0.021 (2)0.0016 (19)0.0045 (18)
C70.040 (2)0.051 (3)0.051 (3)0.024 (2)0.005 (2)0.006 (2)
C10.036 (2)0.040 (2)0.046 (2)0.017 (2)0.0036 (18)0.0010 (19)
O30.047 (2)0.058 (2)0.100 (3)0.0173 (17)0.0097 (18)0.0190 (18)
C60.046 (3)0.035 (2)0.058 (3)0.014 (2)0.005 (2)0.002 (2)
C40.058 (3)0.049 (3)0.061 (3)0.034 (2)0.004 (2)0.001 (2)
C20.039 (2)0.044 (3)0.051 (3)0.019 (2)0.0017 (19)0.0007 (19)
C30.043 (3)0.035 (2)0.051 (3)0.020 (2)0.0026 (19)0.0000 (19)
C130.047 (3)0.043 (3)0.048 (3)0.021 (2)0.008 (2)0.008 (2)
C100.051 (3)0.048 (3)0.069 (3)0.027 (2)0.006 (2)0.001 (2)
O20.081 (2)0.0451 (19)0.111 (3)0.032 (2)0.003 (2)0.0172 (19)
C110.065 (3)0.047 (3)0.079 (4)0.033 (3)0.006 (3)0.000 (2)
C50.041 (3)0.051 (3)0.070 (3)0.022 (2)0.005 (2)0.000 (2)
C90.049 (3)0.044 (3)0.062 (3)0.020 (2)0.002 (2)0.002 (2)
C80.044 (3)0.031 (2)0.046 (2)0.014 (2)0.0038 (19)0.0014 (18)
C120.058 (3)0.035 (2)0.071 (3)0.019 (2)0.001 (2)0.003 (2)
C150.046 (3)0.045 (3)0.081 (3)0.010 (2)0.008 (2)0.009 (2)
C140.060 (4)0.059 (4)0.135 (7)0.028 (3)0.014 (4)0.006 (4)
F1A0.095 (10)0.15 (2)0.23 (3)0.094 (15)0.062 (17)0.12 (2)
F2A0.069 (11)0.075 (12)0.33 (5)0.041 (9)0.09 (2)0.032 (18)
F3A0.137 (12)0.20 (2)0.152 (13)0.107 (15)0.075 (9)0.028 (14)
F1B0.078 (6)0.094 (10)0.26 (2)0.058 (7)0.002 (10)0.056 (12)
F2B0.132 (9)0.257 (19)0.150 (9)0.149 (12)0.068 (7)0.062 (10)
F3B0.060 (7)0.130 (11)0.194 (15)0.047 (7)0.047 (8)0.054 (12)
Geometric parameters (Å, º) top
O4—C131.359 (5)C13—C81.405 (5)
O4—C151.439 (4)C10—C91.376 (5)
O1—C61.299 (4)C10—C111.380 (6)
O1—H10.8200C10—C141.478 (7)
N1—C71.295 (5)C11—C121.389 (6)
N1—C81.426 (5)C11—H110.9300
N2—O31.227 (4)C5—H50.9300
N2—O21.230 (4)C9—C81.378 (5)
N2—C31.443 (5)C9—H90.9300
C7—C11.428 (5)C12—H120.9300
C7—H70.9300C15—H15A0.9600
C1—C21.402 (5)C15—H15B0.9600
C1—C61.428 (5)C15—H15C0.9600
C6—C51.411 (5)C14—F1A1.225 (17)
C4—C51.360 (6)C14—F2A1.228 (19)
C4—C31.397 (5)C14—F3A1.481 (17)
C4—H40.9300C14—F1B1.267 (12)
C2—C31.368 (5)C14—F3B1.295 (13)
C2—H20.9300C14—F2B1.379 (12)
C13—C121.383 (5)
C13—O4—C15117.4 (3)C12—C11—H11119.5
C6—O1—H1109.5C4—C5—C6121.0 (4)
C7—N1—C8124.3 (4)C4—C5—H5119.5
O3—N2—O2122.0 (4)C6—C5—H5119.5
O3—N2—C3119.2 (4)C10—C9—C8120.7 (4)
O2—N2—C3118.8 (4)C10—C9—H9119.6
N1—C7—C1121.0 (4)C8—C9—H9119.6
N1—C7—H7119.5C9—C8—C13119.5 (4)
C1—C7—H7119.5C9—C8—N1124.6 (4)
C2—C1—C6119.1 (4)C13—C8—N1115.8 (4)
C2—C1—C7120.0 (4)C13—C12—C11119.1 (4)
C6—C1—C7120.9 (4)C13—C12—H12120.4
O1—C6—C5119.7 (4)C11—C12—H12120.4
O1—C6—C1121.9 (4)O4—C15—H15A109.5
C5—C6—C1118.4 (4)O4—C15—H15B109.5
C5—C4—C3120.3 (4)H15A—C15—H15B109.5
C5—C4—H4119.9O4—C15—H15C109.5
C3—C4—H4119.9H15A—C15—H15C109.5
C3—C2—C1120.5 (4)H15B—C15—H15C109.5
C3—C2—H2119.8F1A—C14—F2A111.5 (16)
C1—C2—H2119.8F1A—C14—F3A100.7 (13)
C2—C3—C4120.7 (4)F2A—C14—F3A100.8 (18)
C2—C3—N2119.8 (4)F1B—C14—F3B110.7 (11)
C4—C3—N2119.5 (4)F1B—C14—F2B103.7 (10)
O4—C13—C12124.8 (4)F3B—C14—F2B102.1 (10)
O4—C13—C8115.2 (4)F1A—C14—C10115.9 (11)
C12—C13—C8120.0 (4)F2A—C14—C10117.9 (11)
C9—C10—C11119.6 (4)C10—C14—F3A107.1 (8)
C9—C10—C14120.3 (5)F1B—C14—C10117.5 (8)
C11—C10—C14120.1 (5)F3B—C14—C10111.3 (8)
C10—C11—C12121.0 (4)F2B—C14—C10110.2 (6)
C10—C11—H11119.5
C8—N1—C7—C1177.0 (3)C14—C10—C9—C8178.1 (5)
N1—C7—C1—C2177.7 (4)C10—C9—C8—C130.6 (6)
N1—C7—C1—C60.3 (6)C10—C9—C8—N1177.7 (4)
C2—C1—C6—O1180.0 (4)O4—C13—C8—C9177.8 (4)
C7—C1—C6—O11.9 (6)C12—C13—C8—C91.0 (6)
C2—C1—C6—C50.5 (6)O4—C13—C8—N10.4 (5)
C7—C1—C6—C5178.5 (4)C12—C13—C8—N1178.4 (3)
C6—C1—C2—C30.0 (6)C7—N1—C8—C93.1 (6)
C7—C1—C2—C3178.1 (4)C7—N1—C8—C13179.6 (4)
C1—C2—C3—C40.3 (6)O4—C13—C12—C11177.7 (4)
C1—C2—C3—N2179.8 (4)C8—C13—C12—C110.9 (6)
C5—C4—C3—C20.2 (6)C10—C11—C12—C130.4 (7)
C5—C4—C3—N2179.9 (4)C9—C10—C14—F1A136 (2)
O3—N2—C3—C20.7 (6)C11—C10—C14—F1A42 (2)
O2—N2—C3—C2177.9 (4)C9—C10—C14—F2A0 (3)
O3—N2—C3—C4179.4 (4)C11—C10—C14—F2A178 (3)
O2—N2—C3—C42.2 (6)C9—C10—C14—F1B179.0 (14)
C15—O4—C13—C120.5 (6)C11—C10—C14—F1B2.9 (16)
C15—O4—C13—C8178.3 (4)C9—C10—C14—F3B49.9 (13)
C9—C10—C11—C120.1 (7)C11—C10—C14—F3B132.0 (12)
C14—C10—C11—C12178.0 (5)C9—C10—C14—F2B62.5 (13)
C3—C4—C5—C60.3 (6)C11—C10—C14—F2B115.5 (12)
O1—C6—C5—C4179.8 (4)C9—C10—C14—F3A112.9 (16)
C1—C6—C5—C40.6 (6)C11—C10—C14—F3A69.1 (16)
C11—C10—C9—C80.0 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.842.571 (4)148
O1—H1···O40.822.763.468 (4)146
C7—H7···O2i0.932.553.476 (7)176
C9—H9···O2i0.932.463.378 (6)169
Symmetry code: (i) y+4/3, xy1/3, z1/3.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N10.821.842.571 (4)148
O1—H1···O40.822.763.468 (4)146
C7—H7···O2i0.932.553.476 (7)176
C9—H9···O2i0.932.463.378 (6)169
Symmetry code: (i) y+4/3, xy1/3, z1/3.
 

Acknowledgements

The authors wish to acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS II diffractometer (purchased under grant F.279 of the University Research Fund).

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Volume 71| Part 7| July 2015| Pages o466-o467
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