Fluazinam

Jeon, Y.; Kim, J.; Lee, S.; Kim, T.H.

doi:10.1107/S1600536813023210

organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page o1467

doi:10.1107/S1600536813023210

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Fluazinam

Youngeun Jeon,^a Jineun Kim,^a ^* Sangjin Lee ^a and Tae Ho Kim ^a ^*

^aDepartment of Chemistry and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 660-701, Republic of Korea
^*Correspondence e-mail: thkim@gnu.ac.kr, jekim@gnu.ac.kr

(Received 27 July 2013; accepted 19 August 2013; online 23 August 2013)

In the asymmetric unit of the title compound {systematic name: 3-chloro-N-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,6-dinitro-4-(trifluoromethyl)aniline}, C₁₃H₄Cl₂F₆N₄O₄, which is the fungicide fluazinam, the dihedral angle between the pyridine and benzene ring planes is 42.20 (4)°. In the crystal, pairs of N—H⋯F hydrogen bonds link the molecules into inversion dimers which are linked by C—Cl⋯π [Cl⋯ring centroid = 3.3618 (4) A °] and N—O⋯π [O⋯ring centroid = 3.1885 (16) Å] interactions into chains along [100]. In addition, short Cl⋯Cl, O⋯Cl, and F⋯F contacts [3.4676 (7), 3.2371 (13) and 2.7910 (15) Å] are present which connect the chains, yielding a three-dimensional network.

Related literature

For information on the toxicity and fungicidal properties of the title compound, see: Yoshida & Yukimoto (1993 ); Draper et al. (2003 ). For a related structure, see: McCullough et al. (1972 ).

Experimental

Crystal data

C₁₃H₄Cl₂F₆N₄O₄
M_r = 465.10
Triclinic, $[P \overline 1]$
a = 8.9546 (1) Å
b = 9.0724 (1) Å
c = 10.6818 (2) Å
α = 79.556 (1)°
β = 75.420 (1)°
γ = 83.451 (1)°
V = 823.79 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.49 mm⁻¹
T = 173 K
0.30 × 0.18 × 0.15 mm

Data collection

Bruker APEXII CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2006 ) T_min = 0.867, T_max = 0.930
15193 measured reflections
4096 independent reflections
3662 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.085
S = 1.04
4096 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯F3ⁱ	0.88	2.52	3.0690 (15)	121
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813023210/kj2230sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813023210/kj2230Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813023210/kj2230Isup3.cml

checkCIF report

Comment top

The title compound fluazinam, C₁₃H₄Cl₂F₆N₄O₄, is a broad spectrum contact fungicide that can be applied as a foliar spray or soil treatment (Yoshida et al., 1993; Draper et al., 2003) and its crystal structure is reported herein. In this compound (Fig. 1), the dihedral angle between the pyridyl ring and the phenyl ring is 42.20 (4)°. All bond lengths and bond angles are normal and comparable to those observed in the crystal structures of a similar compound (McCullough et al., 1972). In the crystal structure (Fig. 2), an intermolecular N—H···F hydrogen bond is observed (Table 1), giving a dimer structure. In this structure there are both a C3—Cl1···π interaction with the pyridyl ring [Cl1···Cg1ⁱⁱ = 3.3618 (4) Å] and a N1—O1···π interaction with the phenyl ring [O1···Cg2ⁱⁱ = 3.1885 (16) Å]. In addition, short Cl···Cl, O···Cl, and F···F contacts [Cl2···Cl2ⁱⁱⁱ, 3.4676 (7) Å, O3···Cl1^iv, 3.2371 (13) Å, and F3···F6^v, 2.7910 (15) Å] are present [for symmetry codes: (ii), -x+1, -y+1, -z+1, (iii), -x+1, -y+1, -z+2, (iv), x, y - 1, z, and (v), x + 1, y + 1, z + 1]. A three-dimensional network is formed by the hydrogen bond and these interactions.

Related literature top

For information on the toxicity and fungicidal properties of the title compound, see: Yoshida & Yukimoto (1993); Draper et al. (2003). For a related structure, see: McCullough et al. (1972).

Experimental top

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a solution in CH₂Cl₂ gave single crystals suitable for X-ray analysis.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms are shown as small spheres of arbitrary radius.
	Fig. 2. Crystal packing of the title compound with N—H···F hydrogen bonds and weak intermolecular Cl···Cl and F···F interactions shown as dashed lines.

3-Chloro-N-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-2,6-dinitro-4-(trifluoromethyl)aniline top

Crystal data top

C₁₃H₄Cl₂F₆N₄O₄	Z = 2
M_r = 465.10	F(000) = 460
Triclinic, P1	D_x = 1.875 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9546 (1) Å	Cell parameters from 8261 reflections
b = 9.0724 (1) Å	θ = 2.4–28.3°
c = 10.6818 (2) Å	µ = 0.49 mm⁻¹
α = 79.556 (1)°	T = 173 K
β = 75.420 (1)°	Block, yellow
γ = 83.451 (1)°	0.30 × 0.18 × 0.15 mm
V = 823.79 (2) Å³

Data collection top

Bruker APEXII CCD detector diffractometer	4096 independent reflections
Radiation source: fine-focus sealed tube	3662 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ϕ and ω scans	θ_max = 28.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −11→11
T_min = 0.867, T_max = 0.930	k = −12→10
15193 measured reflections	l = −14→14

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0402P)² + 0.3959P] where P = (F_o² + 2F_c²)/3
4096 reflections	(Δ/σ)_max < 0.001
262 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₃H₄Cl₂F₆N₄O₄	γ = 83.451 (1)°
M_r = 465.10	V = 823.79 (2) Å³
Triclinic, P1	Z = 2
a = 8.9546 (1) Å	Mo Kα radiation
b = 9.0724 (1) Å	µ = 0.49 mm⁻¹
c = 10.6818 (2) Å	T = 173 K
α = 79.556 (1)°	0.30 × 0.18 × 0.15 mm
β = 75.420 (1)°

Data collection top

Bruker APEXII CCD detector diffractometer	4096 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2006)	3662 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.930	R_int = 0.022
15193 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 1.04	Δρ_max = 0.47 e Å⁻³
4096 reflections	Δρ_min = −0.45 e Å⁻³
262 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

	x	y	z	U_iso*/U_eq
Cl1	0.83432 (5)	0.72367 (4)	0.34806 (4)	0.03069 (10)
Cl2	0.43809 (5)	0.32745 (5)	0.99480 (4)	0.03760 (11)
F1	1.06852 (11)	0.34123 (11)	0.15585 (9)	0.0342 (2)
F2	0.90981 (11)	0.53398 (12)	0.12664 (9)	0.0369 (2)
F3	1.11164 (11)	0.55470 (11)	0.19484 (10)	0.0357 (2)
F4	0.25749 (13)	−0.25110 (12)	0.84106 (12)	0.0484 (3)
F5	0.07528 (12)	−0.07681 (13)	0.86228 (14)	0.0542 (3)
F6	0.17049 (16)	−0.17401 (14)	1.02625 (11)	0.0572 (3)
N1	0.63148 (15)	0.61200 (13)	0.60382 (12)	0.0257 (3)
N2	0.82927 (13)	0.07922 (13)	0.58834 (12)	0.0239 (2)
N3	0.62868 (14)	0.31709 (14)	0.72658 (11)	0.0234 (2)
H3	0.6329	0.3764	0.7821	0.028*
N4	0.52522 (14)	0.10739 (14)	0.69279 (12)	0.0240 (2)
O1	0.51649 (16)	0.65800 (18)	0.56501 (17)	0.0595 (4)
O2	0.6693 (2)	0.65407 (19)	0.68990 (16)	0.0653 (5)
O3	0.83309 (13)	−0.01445 (12)	0.51781 (11)	0.0321 (2)
O4	0.84483 (13)	0.05111 (13)	0.70083 (11)	0.0321 (2)
C1	1.00024 (17)	0.46373 (17)	0.20469 (14)	0.0257 (3)
C2	0.90782 (15)	0.42479 (15)	0.34387 (13)	0.0210 (3)
C3	0.82543 (16)	0.53636 (15)	0.41309 (13)	0.0210 (3)
C4	0.73336 (15)	0.49449 (15)	0.53729 (13)	0.0209 (3)
C5	0.72421 (15)	0.34551 (15)	0.60148 (13)	0.0197 (3)
C6	0.81363 (15)	0.23826 (15)	0.53006 (13)	0.0204 (3)
C7	0.90021 (16)	0.27574 (15)	0.40317 (13)	0.0215 (3)
H7	0.9548	0.1987	0.3564	0.026*
C8	0.52749 (15)	0.20410 (15)	0.77180 (13)	0.0208 (3)
C9	0.42873 (16)	0.19730 (16)	0.89770 (14)	0.0238 (3)
C10	0.32506 (17)	0.08814 (17)	0.94103 (14)	0.0267 (3)
H10	0.2564	0.0818	1.0253	0.032*
C11	0.32343 (17)	−0.01298 (16)	0.85797 (15)	0.0257 (3)
C12	0.42492 (17)	0.00019 (16)	0.73578 (15)	0.0261 (3)
H12	0.4234	−0.0698	0.6800	0.031*
C13	0.20746 (19)	−0.12907 (18)	0.89734 (17)	0.0332 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0402 (2)	0.01712 (16)	0.03235 (19)	−0.00298 (13)	−0.00704 (15)	0.00063 (13)
Cl2	0.0392 (2)	0.0455 (2)	0.02904 (19)	−0.01359 (17)	0.00518 (15)	−0.02051 (17)
F1	0.0373 (5)	0.0320 (5)	0.0270 (4)	−0.0033 (4)	0.0067 (4)	−0.0076 (4)
F2	0.0418 (5)	0.0452 (6)	0.0211 (4)	0.0003 (4)	−0.0090 (4)	0.0013 (4)
F3	0.0328 (5)	0.0331 (5)	0.0372 (5)	−0.0146 (4)	−0.0007 (4)	0.0018 (4)
F4	0.0441 (6)	0.0303 (5)	0.0704 (8)	−0.0134 (4)	−0.0029 (5)	−0.0154 (5)
F5	0.0303 (5)	0.0468 (7)	0.0869 (9)	−0.0104 (5)	−0.0176 (6)	−0.0038 (6)
F6	0.0738 (8)	0.0510 (7)	0.0409 (6)	−0.0357 (6)	0.0012 (6)	0.0069 (5)
N1	0.0302 (6)	0.0191 (6)	0.0264 (6)	0.0011 (5)	−0.0048 (5)	−0.0047 (5)
N2	0.0218 (6)	0.0194 (6)	0.0264 (6)	−0.0010 (4)	0.0003 (4)	−0.0018 (5)
N3	0.0264 (6)	0.0231 (6)	0.0203 (5)	−0.0068 (4)	0.0004 (4)	−0.0074 (5)
N4	0.0246 (6)	0.0230 (6)	0.0237 (6)	−0.0033 (4)	−0.0018 (4)	−0.0067 (5)
O1	0.0400 (7)	0.0658 (10)	0.0874 (11)	0.0247 (7)	−0.0296 (8)	−0.0471 (9)
O2	0.0887 (12)	0.0629 (10)	0.0628 (10)	0.0380 (9)	−0.0454 (9)	−0.0464 (8)
O3	0.0366 (6)	0.0195 (5)	0.0370 (6)	−0.0018 (4)	0.0002 (5)	−0.0092 (4)
O4	0.0354 (6)	0.0287 (6)	0.0283 (6)	0.0002 (4)	−0.0075 (4)	0.0039 (4)
C1	0.0263 (7)	0.0261 (7)	0.0224 (7)	−0.0049 (5)	−0.0024 (5)	−0.0013 (5)
C2	0.0211 (6)	0.0221 (6)	0.0195 (6)	−0.0036 (5)	−0.0044 (5)	−0.0021 (5)
C3	0.0245 (6)	0.0168 (6)	0.0227 (6)	−0.0032 (5)	−0.0081 (5)	−0.0009 (5)
C4	0.0232 (6)	0.0184 (6)	0.0223 (6)	−0.0007 (5)	−0.0057 (5)	−0.0064 (5)
C5	0.0199 (6)	0.0205 (6)	0.0191 (6)	−0.0034 (5)	−0.0040 (5)	−0.0044 (5)
C6	0.0213 (6)	0.0175 (6)	0.0218 (6)	−0.0019 (5)	−0.0042 (5)	−0.0025 (5)
C7	0.0225 (6)	0.0199 (6)	0.0218 (6)	−0.0011 (5)	−0.0032 (5)	−0.0052 (5)
C8	0.0205 (6)	0.0200 (6)	0.0209 (6)	−0.0011 (5)	−0.0033 (5)	−0.0031 (5)
C9	0.0254 (7)	0.0250 (7)	0.0209 (6)	−0.0016 (5)	−0.0027 (5)	−0.0072 (5)
C10	0.0248 (7)	0.0299 (8)	0.0220 (7)	−0.0044 (6)	0.0000 (5)	−0.0020 (6)
C11	0.0246 (7)	0.0215 (7)	0.0296 (7)	−0.0035 (5)	−0.0054 (5)	−0.0005 (6)
C12	0.0268 (7)	0.0219 (7)	0.0298 (7)	−0.0030 (5)	−0.0046 (6)	−0.0070 (6)
C13	0.0321 (8)	0.0272 (8)	0.0377 (8)	−0.0090 (6)	−0.0032 (6)	−0.0014 (6)

Geometric parameters (Å, º) top

Cl1—C3	1.7180 (13)	N4—C8	1.3280 (18)
Cl2—C9	1.7283 (14)	N4—C12	1.3391 (18)
F1—C1	1.3326 (17)	C1—C2	1.5090 (19)
F2—C1	1.3366 (17)	C2—C7	1.3868 (19)
F3—C1	1.3382 (17)	C2—C3	1.3936 (19)
F4—C13	1.334 (2)	C3—C4	1.3864 (19)
F5—C13	1.340 (2)	C4—C5	1.4017 (19)
F6—C13	1.330 (2)	C5—C6	1.3978 (18)
N1—O2	1.1911 (18)	C6—C7	1.3849 (18)
N1—O1	1.2084 (18)	C7—H7	0.9500
N1—C4	1.4834 (17)	C8—C9	1.4065 (19)
N2—O4	1.2220 (16)	C9—C10	1.373 (2)
N2—O3	1.2263 (16)	C10—C11	1.391 (2)
N2—C6	1.4701 (17)	C10—H10	0.9500
N3—C8	1.3846 (17)	C11—C12	1.384 (2)
N3—C5	1.3906 (17)	C11—C13	1.495 (2)
N3—H3	0.8800	C12—H12	0.9500

O2—N1—O1	125.30 (14)	C7—C6—C5	122.46 (12)
O2—N1—C4	117.99 (13)	C7—C6—N2	115.65 (12)
O1—N1—C4	116.71 (12)	C5—C6—N2	121.78 (12)
O4—N2—O3	125.24 (12)	C6—C7—C2	120.52 (13)
O4—N2—C6	117.51 (12)	C6—C7—H7	119.7
O3—N2—C6	117.15 (12)	C2—C7—H7	119.7
C8—N3—C5	126.00 (12)	N4—C8—N3	118.35 (12)
C8—N3—H3	117.0	N4—C8—C9	122.28 (13)
C5—N3—H3	117.0	N3—C8—C9	119.35 (12)
C8—N4—C12	118.20 (12)	C10—C9—C8	119.38 (13)
F1—C1—F2	107.50 (12)	C10—C9—Cl2	120.99 (11)
F1—C1—F3	107.14 (12)	C8—C9—Cl2	119.63 (11)
F2—C1—F3	106.99 (12)	C9—C10—C11	118.07 (13)
F1—C1—C2	111.51 (12)	C9—C10—H10	121.0
F2—C1—C2	111.11 (12)	C11—C10—H10	121.0
F3—C1—C2	112.33 (12)	C12—C11—C10	119.23 (13)
C7—C2—C3	119.09 (12)	C12—C11—C13	120.38 (14)
C7—C2—C1	119.92 (12)	C10—C11—C13	120.30 (14)
C3—C2—C1	120.96 (12)	N4—C12—C11	122.83 (14)
C4—C3—C2	118.91 (12)	N4—C12—H12	118.6
C4—C3—Cl1	119.39 (11)	C11—C12—H12	118.6
C2—C3—Cl1	121.70 (10)	F6—C13—F4	107.38 (14)
C3—C4—C5	123.74 (12)	F6—C13—F5	106.72 (14)
C3—C4—N1	118.60 (12)	F4—C13—F5	106.11 (14)
C5—C4—N1	117.56 (12)	F6—C13—C11	112.20 (14)
N3—C5—C6	126.22 (12)	F4—C13—C11	112.41 (13)
N3—C5—C4	118.65 (12)	F5—C13—C11	111.63 (13)
C6—C5—C4	115.13 (12)

F1—C1—C2—C7	−1.24 (18)	O3—N2—C6—C7	−41.24 (17)
F2—C1—C2—C7	118.67 (14)	O4—N2—C6—C5	−40.98 (18)
F3—C1—C2—C7	−121.52 (14)	O3—N2—C6—C5	142.43 (13)
F1—C1—C2—C3	−179.22 (12)	C5—C6—C7—C2	3.5 (2)
F2—C1—C2—C3	−59.31 (17)	N2—C6—C7—C2	−172.80 (12)
F3—C1—C2—C3	60.50 (17)	C3—C2—C7—C6	−0.9 (2)
C7—C2—C3—C4	−2.56 (19)	C1—C2—C7—C6	−178.88 (12)
C1—C2—C3—C4	175.44 (12)	C12—N4—C8—N3	−178.61 (13)
C7—C2—C3—Cl1	177.84 (10)	C12—N4—C8—C9	−0.1 (2)
C1—C2—C3—Cl1	−4.16 (18)	C5—N3—C8—N4	3.9 (2)
C2—C3—C4—C5	3.7 (2)	C5—N3—C8—C9	−174.67 (13)
Cl1—C3—C4—C5	−176.73 (10)	N4—C8—C9—C10	−0.5 (2)
C2—C3—C4—N1	−172.68 (12)	N3—C8—C9—C10	178.00 (13)
Cl1—C3—C4—N1	6.93 (17)	N4—C8—C9—Cl2	−179.84 (11)
O2—N1—C4—C3	−104.70 (18)	N3—C8—C9—Cl2	−1.30 (19)
O1—N1—C4—C3	74.84 (19)	C8—C9—C10—C11	0.6 (2)
O2—N1—C4—C5	78.73 (19)	Cl2—C9—C10—C11	179.93 (11)
O1—N1—C4—C5	−101.72 (17)	C9—C10—C11—C12	−0.2 (2)
C8—N3—C5—C6	−43.9 (2)	C9—C10—C11—C13	−176.82 (14)
C8—N3—C5—C4	135.41 (14)	C8—N4—C12—C11	0.5 (2)
C3—C4—C5—N3	179.48 (12)	C10—C11—C12—N4	−0.4 (2)
N1—C4—C5—N3	−4.14 (18)	C13—C11—C12—N4	176.21 (14)
C3—C4—C5—C6	−1.2 (2)	C12—C11—C13—F6	151.47 (15)
N1—C4—C5—C6	175.22 (12)	C10—C11—C13—F6	−31.9 (2)
N3—C5—C6—C7	176.86 (13)	C12—C11—C13—F4	30.3 (2)
C4—C5—C6—C7	−2.45 (19)	C10—C11—C13—F4	−153.10 (14)
N3—C5—C6—N2	−7.1 (2)	C12—C11—C13—F5	−88.78 (18)
C4—C5—C6—N2	173.63 (12)	C10—C11—C13—F5	87.80 (19)
O4—N2—C6—C7	135.34 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···F3ⁱ	0.88	2.52	3.0690 (15)	121

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···F3ⁱ	0.88	2.52	3.0690 (15)	121.2

Symmetry code: (i) −x+2, −y+1, −z+1.

Acknowledgements

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2012R1A1B3003337).

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