Synthesis and crystal structure of (E)-2-benzyl-1,3-di­phenyl­iso­thio­uronium iodide

Kang, S.; Kim, T.H.; Kwak, C.-H.

doi:10.1107/S2056989021013086

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ISSN: 2056-9890

Volume 78| Part 1| January 2022| Pages 51-53

https://doi.org/10.1107/S2056989021013086

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Synthesis and crystal structure of (E)-2-benzyl-1,3-diphenylisothiouronium iodide

Sungmin Kang,^a Taek Hyeon Kim ^a ‡ and Chee-Hun Kwak ^b ^*

^aSchool of Chemical Engineering, College of Engineering, Chonnam National, University, Gwangju, 61186, South Korea, and ^bDepartment of Chemistry Education, Sunchon National University, 255 Jungang-ro, Sunchon, 57922, South Korea
^*Correspondence e-mail: chkwak@sunchon.ac.kr

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 1 November 2021; accepted 9 December 2021; online 1 January 2022)

In the title molecular salt, C₂₀H₁₉N₂S⁺·I⁻, prepared by the reaction of 1,3-diphenylthiourea and benzyl iodide, the C—S—C thioether bond angle is 101.66 (9)° and electrons are delocalized over the N⁺= C—N skeleton. The dihedral angle between the aromatic rings attached to the N atoms is 40.60 (9)°. In the crystal, N—H⋯I hydrogen bonds link the components into [100] chains.

Keywords: crystal structure; thioether; N—H⋯I hydrogen bonding.

CCDC reference: 2127354

1. Chemical context

Isothiouronium salts containing an R–S–C–(NHR)₂⁺ moiety have been investigated as their hydrogen–bonding motifs for molecular recognition of anions (Yeo & Hong, 1998 ; Kubo et al., 2000 ; Kato et al., 2004 ; Nguyen et al., 2009 ; Nguyen & Kim, 2010 ) and as organocatalysts (Nguyen & Kim, 2011 , 2012 ; Lee et al., 2018 ; Kang et al., 2019 ). The isothiouronium group could enhance the acidity of their NH groups compared with thiourea and therefore be used as prospective alternative for thiourea. In addition, the chemical modification of the isothiouronium skeleton is readily performed using alkylation reactions of thiourea. As part of our work in this area, the synthesis and single-crystal structure of the title molecular salt, C₂₀H₁₉N₂S⁺·I⁻ are reported herein.

2. Structural commentary

The title compound, C₂₀H₁₉N₂S⁺·I⁻ (Fig. 1), is a molecular salt that arose from the reaction of 1,3-diphenylthiourea and benzyl iodide. There are three benzene rings, C1–C6 (I), C9–C14 (II) and C15–C20 (III) in the cation and the dihedral angles I/II, II/III and I/III are 50.36 (8), 40.60 (9) and 85.45 (9)°, respectively. In the cation, the N-[(phenylamino)methylene]benzenaminium and toluyl units are linked to the sulfur atom as a thioether. The C7—S1 and C8—S1 bond lengths are 1.823 (2) and 1.751 (2) Å, respectively, and the C—S—C bond angle is 101.66 (9)°. The conformation of C1 and C8 about the C7—S1 bond is gauche [C1—C7—S1—C8 = 49.53 (16)°]. The C—S—C bond angle in the title compound is somewhat smaller than that for di-p-tolyl sulfide (109°; Blackmore & Abrahams, 1955 ) or the angle (107.8°) in oligomeric [ArCOArSArCOAr] (Ar = 1,4-phenylene; Colquhoun et al., 1999 ) in which the aromatic rings are nearly coplanar. Rather, it is closer to that seen in diethyl sulfide [99.05 (4)°; Iijima et al., 1977 ]. This result can be explained by the large dihedral angle between the benzene rings in the title compound. In the N-[(phenylamino)methylene]benzenaminium moiety of the title cation, the π-electrons of the iminium double bond are delocalized over the N1—C6—N2 skeleton [the C8—N1 and C8—N2 bond distances are 1.319 (2) and 1.332 (2) Å, respectively, and N1—C8—N2 = 124.53 (16)°].

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at at the 30% probability level.

3. Supramolecular features

In the crystal, the cations and anions are linked by almost linear N—H⋯I hydrogen bonds (Fig. 2, Table 1), generating [100] chains of alternating cations and anions, with adjacent species in the chain related by simple translation. No significant aromatic π–π stacking interactions occur, the shortest centroid–centroid separation being greater than 4.7 Å.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯I1ⁱ	0.80 (3)	2.69 (3)	3.4781 (17)	171 (2)
N2—H2N⋯I1ⁱⁱ	0.80 (3)	2.73 (3)	3.5242 (17)	169 (2)
Symmetry codes: (i) ; (ii) .

Figure 2
A view of a fragment of the [100] chain arising from N—H⋯I hydrogen bonds.

4. Database survey

A search of the Cambridge Structural Database (CSD, via CCDC Access Structures, November 2021; Groom et al., 2016 ) resulted in 30 structures using isothiouronium as the keyword: 26 of them have a thioether skeleton. No results were found for 2-benzyl-1,3-diphenylisothiouronium or N-[(phenylamino)methylene]benzenaminium but the compound most similar to the title compound is S-benzylisothiouronium chloride (Barker & Powell, 1998 ). The bond angles of the thioether group in the S-benzylisothiouronium salts similar to the title compound are the range 102.6 to 104.8°, depending on the counter-anions (Hemalatha & Veeravazhuthi, 2008 ; Ishii et al., 2000 ; Pope & Boeyens, 1975 ).

5. Synthesis and crystallization

1,3-Diphenylthiourea (4.4 mmol) was added to a solution of benzyl iodide (13.2 mmol) in dry dichloromethane at room temperature. The reaction mixture was then stirred for 24 h and concentrated in vacuo. The residue was purified via flash chromatography (hexane:ethyl acetate = 8:2), to give a the title compound as a yellow solid (1.14 g, yield 58%). A solution of isothiouronium iodide in methanol was slowly evaporated at room temperature to give crystals of the title compound: m.p. 442–443 K; ¹H NMR (300 MHz, DMSO): δ 7.21–7.39 (m, 15 H), δ 4.45 (s, 2 H); HR TOF–MS for C₂₀H₁₈N₂S: calculated 318.1186 (M⁺), found 318.1185 (M⁺).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically (C—H = 0.94–0.98 Å, N—H = 0.80 Å) and refined using a riding model withU_iso(H) = 1.2U_eq(carrier).

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₉N₂S⁺·I⁻
M_r	446.33
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	223
a, b, c (Å)	8.6382 (3), 9.8182 (3), 12.1922 (4)
α, β, γ (°)	77.2839 (12), 85.1708 (11), 74.7224 (10)
V (Å³)	972.66 (6)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.76
Crystal size (mm)	0.27 × 0.21 × 0.15

Data collection
Diffractometer	PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.649, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	31969, 4853, 4594
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.063, 1.09
No. of reflections	4853
No. of parameters	225
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.43, −1.04
Computer programs: APEX2 and SAINT (Bruker, 2016), SHELXTL (Sheldrick, 2008 ), SHELXL2014/7 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2020 ).

Supporting information

CCDC reference: 2127354

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989021013086/hb7997sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989021013086/hb7997Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989021013086/hb7997Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2020); software used to prepare material for publication: SHELXTL ((Sheldrick, 2008)).

N-[(Benzylsulfanyl)(phenylamino)methylidene]anilinium iodide top

Crystal data top

C₂₀H₁₉N₂S⁺·I⁻	Z = 2
M_r = 446.33	F(000) = 444
Triclinic, P1	D_x = 1.524 Mg m⁻³
a = 8.6382 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.8182 (3) Å	Cell parameters from 9837 reflections
c = 12.1922 (4) Å	θ = 2.5–28.3°
α = 77.2839 (12)°	µ = 1.76 mm⁻¹
β = 85.1708 (11)°	T = 223 K
γ = 74.7224 (10)°	Block, colourless
V = 972.66 (6) Å³	0.27 × 0.21 × 0.15 mm

Data collection top

PHOTON 100 CMOS diffractometer	4594 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2016)	θ_max = 28.3°, θ_min = 2.2°
T_min = 0.649, T_max = 0.746	h = −11→11
31969 measured reflections	k = −13→13
4853 independent reflections	l = −16→16

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.063	w = 1/[σ²(F_o²) + (0.0253P)² + 0.8267P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
4853 reflections	Δρ_max = 1.43 e Å⁻³
225 parameters	Δρ_min = −1.03 e Å⁻³
0 restraints

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.

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

	x	y	z	U_iso*/U_eq
I1	0.26986 (2)	0.34036 (2)	0.87755 (2)	0.04395 (6)
C1	0.3315 (2)	0.4161 (2)	0.28202 (17)	0.0316 (4)
C2	0.1753 (3)	0.4055 (3)	0.3116 (2)	0.0421 (5)
H2	0.1020	0.4181	0.2552	0.051*
C3	0.1274 (4)	0.3766 (3)	0.4237 (2)	0.0581 (7)
H3	0.0216	0.3697	0.4430	0.070*
C4	0.2340 (5)	0.3578 (3)	0.5072 (2)	0.0648 (8)
H4	0.2012	0.3380	0.5833	0.078*
C5	0.3880 (4)	0.3682 (3)	0.4786 (2)	0.0594 (7)
H5	0.4609	0.3550	0.5355	0.071*
C6	0.4373 (3)	0.3982 (2)	0.3666 (2)	0.0434 (5)
H6	0.5427	0.4064	0.3479	0.052*
C7	0.3883 (2)	0.4451 (2)	0.16100 (17)	0.0330 (4)
H7A	0.4058	0.3566	0.1320	0.040*
H7B	0.4917	0.4696	0.1574	0.040*
S1	0.24895 (6)	0.59022 (5)	0.07051 (4)	0.03231 (10)
C8	0.2092 (2)	0.72734 (19)	0.14740 (14)	0.0252 (3)
N1	0.32455 (19)	0.75297 (18)	0.19789 (14)	0.0278 (3)
H1N	0.415 (3)	0.724 (3)	0.177 (2)	0.036 (6)*
C9	0.3042 (2)	0.82793 (19)	0.28816 (15)	0.0267 (3)
C10	0.2028 (2)	0.7956 (2)	0.37864 (17)	0.0337 (4)
H10	0.1474	0.7243	0.3814	0.040*
C11	0.1841 (3)	0.8703 (3)	0.46533 (18)	0.0426 (5)
H11	0.1147	0.8502	0.5270	0.051*
C12	0.2668 (3)	0.9740 (3)	0.46136 (19)	0.0444 (5)
H12	0.2526	1.0250	0.5198	0.053*
C13	0.3700 (3)	1.0030 (2)	0.3723 (2)	0.0421 (5)
H13	0.4272	1.0727	0.3708	0.051*
C14	0.3903 (2)	0.9300 (2)	0.28442 (18)	0.0343 (4)
H14	0.4612	0.9493	0.2236	0.041*
N2	0.05644 (19)	0.80281 (17)	0.14673 (14)	0.0276 (3)
H2N	−0.010 (3)	0.765 (3)	0.134 (2)	0.034 (6)*
C15	−0.0057 (2)	0.94592 (19)	0.16504 (15)	0.0259 (3)
C16	0.0742 (2)	1.0527 (2)	0.12339 (16)	0.0310 (4)
H16	0.1723	1.0316	0.0832	0.037*
C17	0.0078 (3)	1.1909 (2)	0.14165 (18)	0.0380 (4)
H17	0.0622	1.2636	0.1148	0.046*
C18	−0.1379 (3)	1.2225 (2)	0.19912 (19)	0.0422 (5)
H18	−0.1816	1.3161	0.2122	0.051*
C19	−0.2187 (3)	1.1169 (2)	0.2371 (2)	0.0427 (5)
H19	−0.3192	1.1396	0.2743	0.051*
C20	−0.1536 (2)	0.9773 (2)	0.22119 (18)	0.0349 (4)
H20	−0.2086	0.9051	0.2479	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02782 (7)	0.04822 (9)	0.06798 (11)	−0.01720 (6)	0.01189 (6)	−0.03314 (7)
C1	0.0347 (10)	0.0226 (8)	0.0376 (10)	−0.0046 (7)	−0.0028 (8)	−0.0091 (7)
C2	0.0428 (12)	0.0421 (11)	0.0462 (12)	−0.0177 (9)	0.0024 (9)	−0.0122 (9)
C3	0.0661 (17)	0.0529 (15)	0.0582 (16)	−0.0274 (13)	0.0190 (13)	−0.0102 (12)
C4	0.099 (2)	0.0473 (15)	0.0396 (13)	−0.0139 (15)	0.0082 (14)	−0.0006 (11)
C5	0.079 (2)	0.0483 (14)	0.0424 (13)	0.0001 (13)	−0.0211 (13)	−0.0048 (11)
C6	0.0419 (12)	0.0377 (11)	0.0474 (12)	0.0001 (9)	−0.0127 (10)	−0.0102 (9)
C7	0.0294 (9)	0.0298 (9)	0.0393 (10)	−0.0018 (7)	−0.0002 (8)	−0.0136 (8)
S1	0.0365 (2)	0.0321 (2)	0.0301 (2)	−0.00373 (18)	−0.00340 (18)	−0.01509 (18)
C8	0.0254 (8)	0.0257 (8)	0.0253 (8)	−0.0059 (6)	0.0010 (6)	−0.0083 (6)
N1	0.0199 (7)	0.0326 (8)	0.0330 (8)	−0.0045 (6)	0.0014 (6)	−0.0146 (6)
C9	0.0231 (8)	0.0283 (8)	0.0294 (8)	−0.0030 (6)	−0.0050 (6)	−0.0104 (7)
C10	0.0331 (9)	0.0385 (10)	0.0329 (9)	−0.0115 (8)	−0.0011 (7)	−0.0117 (8)
C11	0.0459 (12)	0.0521 (13)	0.0331 (10)	−0.0119 (10)	0.0023 (9)	−0.0172 (9)
C12	0.0509 (13)	0.0452 (12)	0.0415 (11)	−0.0055 (10)	−0.0079 (10)	−0.0237 (10)
C13	0.0450 (12)	0.0372 (11)	0.0514 (13)	−0.0139 (9)	−0.0106 (10)	−0.0167 (9)
C14	0.0322 (9)	0.0348 (10)	0.0393 (10)	−0.0110 (8)	−0.0029 (8)	−0.0106 (8)
N2	0.0229 (7)	0.0292 (8)	0.0338 (8)	−0.0063 (6)	−0.0039 (6)	−0.0122 (6)
C15	0.0253 (8)	0.0262 (8)	0.0257 (8)	−0.0028 (6)	−0.0054 (6)	−0.0070 (6)
C16	0.0321 (9)	0.0324 (9)	0.0274 (8)	−0.0074 (7)	−0.0021 (7)	−0.0043 (7)
C17	0.0489 (12)	0.0300 (9)	0.0353 (10)	−0.0118 (9)	−0.0066 (9)	−0.0025 (8)
C18	0.0523 (13)	0.0287 (10)	0.0416 (11)	0.0008 (9)	−0.0057 (9)	−0.0108 (8)
C19	0.0368 (11)	0.0405 (11)	0.0460 (12)	0.0010 (9)	0.0052 (9)	−0.0143 (9)
C20	0.0300 (9)	0.0342 (10)	0.0406 (10)	−0.0071 (8)	0.0024 (8)	−0.0105 (8)

Geometric parameters (Å, º) top

C1—C6	1.386 (3)	C10—C11	1.390 (3)
C1—C2	1.392 (3)	C10—H10	0.9400
C1—C7	1.505 (3)	C11—C12	1.381 (3)
C2—C3	1.383 (4)	C11—H11	0.9400
C2—H2	0.9400	C12—C13	1.374 (4)
C3—C4	1.381 (5)	C12—H12	0.9400
C3—H3	0.9400	C13—C14	1.391 (3)
C4—C5	1.371 (5)	C13—H13	0.9400
C4—H4	0.9400	C14—H14	0.9400
C5—C6	1.388 (4)	N2—C15	1.426 (2)
C5—H5	0.9400	N2—H2N	0.81 (3)
C6—H6	0.9400	C15—C16	1.386 (3)
C7—S1	1.823 (2)	C15—C20	1.391 (3)
C7—H7A	0.9800	C16—C17	1.386 (3)
C7—H7B	0.9800	C16—H16	0.9400
S1—C8	1.7513 (18)	C17—C18	1.383 (3)
C8—N1	1.319 (2)	C17—H17	0.9400
C8—N2	1.332 (2)	C18—C19	1.376 (4)
N1—C9	1.428 (2)	C18—H18	0.9400
N1—H1N	0.80 (3)	C19—C20	1.388 (3)
C9—C10	1.384 (3)	C19—H19	0.9400
C9—C14	1.388 (3)	C20—H20	0.9400

C6—C1—C2	118.9 (2)	C9—C10—H10	120.5
C6—C1—C7	119.46 (19)	C11—C10—H10	120.5
C2—C1—C7	121.67 (19)	C12—C11—C10	120.3 (2)
C3—C2—C1	120.3 (2)	C12—C11—H11	119.9
C3—C2—H2	119.8	C10—C11—H11	119.9
C1—C2—H2	119.8	C13—C12—C11	120.3 (2)
C4—C3—C2	120.4 (3)	C13—C12—H12	119.9
C4—C3—H3	119.8	C11—C12—H12	119.9
C2—C3—H3	119.8	C12—C13—C14	120.5 (2)
C5—C4—C3	119.6 (3)	C12—C13—H13	119.8
C5—C4—H4	120.2	C14—C13—H13	119.8
C3—C4—H4	120.2	C9—C14—C13	118.8 (2)
C4—C5—C6	120.6 (3)	C9—C14—H14	120.6
C4—C5—H5	119.7	C13—C14—H14	120.6
C6—C5—H5	119.7	C8—N2—C15	127.80 (16)
C1—C6—C5	120.2 (2)	C8—N2—H2N	117.4 (18)
C1—C6—H6	119.9	C15—N2—H2N	114.8 (18)
C5—C6—H6	119.9	C16—C15—C20	120.73 (17)
C1—C7—S1	113.83 (13)	C16—C15—N2	121.30 (17)
C1—C7—H7A	108.8	C20—C15—N2	117.89 (17)
S1—C7—H7A	108.8	C17—C16—C15	119.28 (19)
C1—C7—H7B	108.8	C17—C16—H16	120.4
S1—C7—H7B	108.8	C15—C16—H16	120.4
H7A—C7—H7B	107.7	C18—C17—C16	120.3 (2)
C8—S1—C7	101.66 (9)	C18—C17—H17	119.8
N1—C8—N2	124.53 (16)	C16—C17—H17	119.8
N1—C8—S1	121.30 (14)	C19—C18—C17	120.0 (2)
N2—C8—S1	114.14 (13)	C19—C18—H18	120.0
C8—N1—C9	126.22 (16)	C17—C18—H18	120.0
C8—N1—H1N	118.0 (19)	C18—C19—C20	120.7 (2)
C9—N1—H1N	115.7 (19)	C18—C19—H19	119.7
C10—C9—C14	121.18 (18)	C20—C19—H19	119.7
C10—C9—N1	119.87 (17)	C19—C20—C15	118.9 (2)
C14—C9—N1	118.93 (17)	C19—C20—H20	120.5
C9—C10—C11	119.0 (2)	C15—C20—H20	120.5

C6—C1—C2—C3	−0.5 (3)	C9—C10—C11—C12	−0.6 (3)
C7—C1—C2—C3	179.0 (2)	C10—C11—C12—C13	−0.8 (4)
C1—C2—C3—C4	0.0 (4)	C11—C12—C13—C14	1.0 (4)
C2—C3—C4—C5	0.1 (4)	C10—C9—C14—C13	−1.7 (3)
C3—C4—C5—C6	0.3 (4)	N1—C9—C14—C13	179.86 (18)
C2—C1—C6—C5	0.9 (3)	C12—C13—C14—C9	0.3 (3)
C7—C1—C6—C5	−178.6 (2)	N1—C8—N2—C15	21.8 (3)
C4—C5—C6—C1	−0.8 (4)	S1—C8—N2—C15	−156.34 (15)
C6—C1—C7—S1	−134.43 (17)	C8—N2—C15—C16	38.5 (3)
C2—C1—C7—S1	46.1 (2)	C8—N2—C15—C20	−144.78 (19)
C1—C7—S1—C8	49.53 (16)	C20—C15—C16—C17	2.2 (3)
C7—S1—C8—N1	41.74 (18)	N2—C15—C16—C17	178.92 (17)
C7—S1—C8—N2	−140.01 (15)	C15—C16—C17—C18	−1.1 (3)
N2—C8—N1—C9	22.1 (3)	C16—C17—C18—C19	−0.9 (3)
S1—C8—N1—C9	−159.85 (15)	C17—C18—C19—C20	1.8 (4)
C8—N1—C9—C10	46.0 (3)	C18—C19—C20—C15	−0.7 (3)
C8—N1—C9—C14	−135.6 (2)	C16—C15—C20—C19	−1.4 (3)
C14—C9—C10—C11	1.9 (3)	N2—C15—C20—C19	−178.16 (18)
N1—C9—C10—C11	−179.70 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···I1ⁱ	0.80 (3)	2.69 (3)	3.4781 (17)	171 (2)
N2—H2N···I1ⁱⁱ	0.80 (3)	2.73 (3)	3.5242 (17)	169 (2)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, −y+1, −z+1.

Footnotes

‡Additional correspondence author, email: thkim@jnu.ac.kr.

Acknowledgements

The X-ray data were obtained from the Western Seoul Center of Korea Basic Science Institute.

Funding information

This research was supported by Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (2018R1D1A3B07040876 and 2021R1I1A3A04037235).

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