(2,2′-Bi­pyridine-κ2N,N′)(pyridine-2,6-di­carboxyl­ato-κ2N,O)palladium(II) monohydrate

Ha, K.

doi:10.1107/S2414314619016250

metal-organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 12| December 2019| x191625

https://doi.org/10.1107/S2414314619016250

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(2,2′-Bipyridine-κ²N,N′)(pyridine-2,6-dicarboxylato-κ²N,O)palladium(II) monohydrate

Kwang Ha ^a ^*

^aChonnam National University, School of Chemical Engineering, Research Institute of Catalysis, Gwangju, Republic of Korea
^*Correspondence e-mail: hakwang@chonnam.ac.kr

Edited by J. Simpson, University of Otago, New Zealand (Received 29 November 2019; accepted 3 December 2019; online 6 December 2019)

In the title compound, [Pd(C₇H₃NO₄)(C₁₀H₈N₂)]·H₂O, the Pd^II cation is four-coordinated in a distorted square-planar coordination geometry defined by the two N atoms of the 2,2′-bipyridine ligand, one O atom and one N atom from the pyridine-2,6-dicarboxylate anion. The complex and solvent water molecule are linked by intermolecular hydrogen bonds. In the crystal, the complex molecules are stacked in columns along the a axis.

Keywords: crystal structure; palladium(II) complex; bipyridine; pyridine-2,6-dicarboxylic acid.

CCDC reference: 1969632

Structure description

With reference to the title compound, [Pd(dipic)(bipy)]·H₂O (dipic = pyridine-2,6-dicarboxylate; bipy = 2,2′-bipyridine), the crystal structures of related Pd^II complexes [Pd(dipic)(phen)]·4H₂O and [Pd(dipic23)(bipy)]·3H₂O (phen = 1,10-phenanthroline; dipic23 = pyridine-2,3-dicarboxylate) have been determined previously (Wang & Okabe, 2005 ).

In the title complex, the central Pd^II cation is four-coordinated in a distorted square-planar coordination geometry defined by the N1 and N2 atoms of the bidentate bipy ligand, the O3 and N3 atoms of the di-anionic dipic ligand. An intramolecular C10—H10⋯·O3 hydrogen bond further stabilizes the complex (Fig. 1, Table 1). The tight O—Pd—N and N—Pd—N chelating angles of <O3—Pd1—N3 = 81.07 (10)° and <N1—Pd1—N2 = 80.21 (12)°, and the steric interactions between the non-coordinating carboxylate group and the (N1–C5) pyridyl ring contribute to the distortion of the square plane. The Pd—N and Pd—O bonds are almost equal [1.992 (3)-2.038 (3) Å] and the nearly planar pyridyl rings of the bipy ligand are slightly twisted with a dihedral angle of 12.6 (1)° between them. The dihedral angle between the least-squares plane [maximum deviation = 0.176 (2) Å] of the bipy ligand and the pyridyl ring of the dipic ligand is 30.6 (1)°.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5A⋯O1ⁱ	0.84	1.96	2.792 (4)	174
O5—H5B⋯O2ⁱⁱ	0.84	1.99	2.790 (4)	160
C2—H2⋯O5ⁱⁱⁱ	0.94	2.59	3.460 (5)	154
C3—H3⋯O2^iv	0.94	2.31	3.245 (4)	173
C4—H4⋯O1^v	0.94	2.35	3.261 (4)	162
C8—H8⋯O5^v	0.94	2.47	2.997 (5)	116
C10—H10⋯O3	0.94	2.55	3.083 (4)	117
C13—H13⋯O4^vi	0.94	2.43	3.336 (5)	161
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x, y, z+1; (iv) -x+1, -y+1, -z+2; (v) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (vi) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound showing the atom labelling and displacement ellipsoids drawn at the 50% probability level for non-H atoms. The intramolecular hydrogen bond is drawn as a double-dashed line.

In the crystal structure (Fig. 2), the complex and solvent molecules form intermolecular O—H⋯O and C—H⋯O hydrogen bonds (Table 1). The complex molecules are stacked in columns along the a axis. In the columns, numerous intermolecular π–π interactions between adjacent pyridyl rings are present. For Cg1 (the centroid of ring N1–C5) and Cg2ⁱ [the centroid of ring N2—C10; symmetry code: (i) x, $[{3\over 2}]$ − y, $[{1\over 2}]$ + z], the centroid–centroid distance is 3.657 (2) Å and the dihedral angle between the ring planes is 12.4 (2)°.

Figure 2
The packing in the crystal structure of the title compound, viewed approximately along the a axis. Hydrogen-bonding interactions are drawn as dashed lines.

Synthesis and crystallization

To a solution of Pd(CH₃CO₂)₂ (0.2036 g, 0.907 mmol) in acetone (25 ml) and MeOH (5 ml) were added pyridine-2,6-dicarboxylic acid (0.1520 g, 0.910 mmol) and 2,2′-bipyridine (0.1423 g, 0.911 mmol), and stirred for 2 h at room temperature. The precipitate that formed was separated by filtration, washed with acetone, and dried at 333 K, to give a yellow powder (0.3605 g). Yellow crystals suitable for X-ray analysis were obtained by slow evaporation from an ethanol solution at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	[Pd(C₇H₃NO₄)(C₁₀H₈N₂)]·H₂O
M_r	445.70
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	223
a, b, c (Å)	12.9031 (10), 12.1751 (10), 10.4256 (7)
β (°)	106.246 (2)
V (Å³)	1572.4 (2)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	1.22
Crystal size (mm)	0.17 × 0.11 × 0.06

Data collection
Diffractometer	PHOTON 100 CMOS detector
Absorption correction	Multi-scan (SADABS; Bruker, 2016 )
T_min, T_max	0.683, 0.745
No. of measured, independent and observed [I > 2σ(I)] reflections	40118, 3110, 2325
R_int	0.110
(sin θ/λ)_max (Å⁻¹)	0.619

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.061, 1.06
No. of reflections	3110
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.69, −0.71
Computer programs: APEX2 and SAINT (Bruker, 2016), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1969632

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314619016250/sj4212sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619016250/sj4212Isup2.hkl

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: SHELXL2014 (Sheldrick, 2015); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

(2,2'-Bipyridine-κ²N,N')(pyridine-2,6-dicarboxylato-κ²N,O)palladium(II) monohydrate top

Crystal data top

[Pd(C₇H₃NO₄)(C₁₀H₈N₂)]·H₂O	F(000) = 888
M_r = 445.70	D_x = 1.883 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.9031 (10) Å	Cell parameters from 8336 reflections
b = 12.1751 (10) Å	θ = 2.4–26.0°
c = 10.4256 (7) Å	µ = 1.22 mm⁻¹
β = 106.246 (2)°	T = 223 K
V = 1572.4 (2) Å³	Rod, yellow
Z = 4	0.17 × 0.11 × 0.06 mm

Data collection top

PHOTON 100 CMOS detector diffractometer	2325 reflections with I > 2σ(I)
Radiation source: sealed tube	R_int = 0.110
φ and ω scans	θ_max = 26.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2016)	h = −15→15
T_min = 0.683, T_max = 0.745	k = −15→15
40118 measured reflections	l = −12→12
3110 independent reflections

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)] = 0.030	Hydrogen site location: mixed
wR(F²) = 0.061	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0181P)² + 2.4725P] where P = (F_o² + 2F_c²)/3
3110 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.69 e Å⁻³
0 restraints	Δρ_min = −0.71 e Å⁻³

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
Pd1	0.18480 (2)	0.62619 (2)	0.56502 (2)	0.01608 (8)
O1	0.40895 (19)	0.5298 (2)	0.5905 (2)	0.0247 (6)
O2	0.4447 (2)	0.3619 (2)	0.6786 (2)	0.0345 (7)
O3	0.06841 (19)	0.6372 (2)	0.3919 (2)	0.0229 (6)
O4	−0.0568 (2)	0.5284 (2)	0.2619 (2)	0.0313 (7)
N1	0.2794 (2)	0.6223 (3)	0.7542 (2)	0.0179 (6)
N2	0.1816 (2)	0.7845 (2)	0.6120 (3)	0.0172 (6)
N3	0.1930 (2)	0.4707 (2)	0.4962 (2)	0.0169 (6)
C1	0.3089 (3)	0.5325 (3)	0.8287 (3)	0.0201 (8)
H1	0.2861	0.4633	0.7914	0.024*
C2	0.3721 (3)	0.5389 (3)	0.9590 (3)	0.0240 (9)
H2	0.3906	0.4748	1.0107	0.029*
C3	0.4080 (3)	0.6398 (3)	1.0131 (3)	0.0239 (8)
H3	0.4541	0.6448	1.1004	0.029*
C4	0.3758 (3)	0.7334 (3)	0.9383 (3)	0.0220 (8)
H4	0.3984	0.8030	0.9744	0.026*
C5	0.3094 (3)	0.7229 (3)	0.8088 (3)	0.0170 (8)
C6	0.2582 (3)	0.8153 (3)	0.7249 (3)	0.0165 (8)
C7	0.2802 (3)	0.9246 (3)	0.7548 (3)	0.0215 (8)
H7	0.3349	0.9451	0.8314	0.026*
C8	0.2205 (3)	1.0037 (3)	0.6703 (3)	0.0247 (8)
H8	0.2335	1.0787	0.6897	0.030*
C9	0.1419 (3)	0.9715 (3)	0.5575 (4)	0.0246 (8)
H9	0.1002	1.0242	0.4996	0.030*
C10	0.1252 (3)	0.8617 (3)	0.5306 (3)	0.0240 (8)
H10	0.0725	0.8400	0.4527	0.029*
C11	0.2729 (3)	0.3955 (3)	0.5297 (3)	0.0195 (8)
C12	0.2544 (3)	0.2891 (3)	0.4812 (3)	0.0291 (9)
H12	0.3095	0.2363	0.5069	0.035*
C13	0.1559 (3)	0.2602 (3)	0.3956 (4)	0.0308 (9)
H13	0.1419	0.1874	0.3660	0.037*
C14	0.0777 (3)	0.3407 (3)	0.3540 (3)	0.0246 (9)
H14	0.0111	0.3241	0.2924	0.029*
C15	0.0991 (3)	0.4453 (3)	0.4042 (3)	0.0187 (8)
C16	0.3866 (3)	0.4333 (3)	0.6088 (3)	0.0194 (8)
C17	0.0287 (3)	0.5420 (3)	0.3484 (3)	0.0215 (8)
O5	0.4222 (2)	0.3608 (3)	0.2280 (3)	0.0690 (11)
H5A	0.4744	0.3891	0.2854	0.104*
H5B	0.4281	0.2921	0.2325	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pd1	0.01601 (14)	0.01669 (13)	0.01266 (12)	0.00058 (13)	−0.00074 (9)	−0.00092 (12)
O1	0.0225 (14)	0.0201 (14)	0.0276 (13)	−0.0024 (11)	0.0008 (11)	−0.0002 (11)
O2	0.0296 (15)	0.0246 (15)	0.0370 (15)	0.0053 (13)	−0.0113 (12)	0.0063 (13)
O3	0.0223 (13)	0.0220 (14)	0.0182 (12)	0.0034 (12)	−0.0045 (10)	−0.0004 (11)
O4	0.0222 (15)	0.0333 (16)	0.0290 (14)	−0.0037 (12)	−0.0083 (12)	−0.0014 (12)
N1	0.0173 (15)	0.0217 (15)	0.0152 (13)	0.0002 (14)	0.0055 (11)	0.0002 (13)
N2	0.0152 (15)	0.0223 (16)	0.0143 (14)	0.0021 (13)	0.0042 (12)	−0.0014 (12)
N3	0.0203 (17)	0.0166 (16)	0.0118 (14)	−0.0040 (13)	0.0011 (12)	0.0024 (12)
C1	0.021 (2)	0.019 (2)	0.0208 (18)	0.0001 (16)	0.0075 (16)	0.0022 (15)
C2	0.020 (2)	0.035 (2)	0.0174 (18)	0.0067 (18)	0.0061 (15)	0.0068 (16)
C3	0.0214 (19)	0.036 (2)	0.0111 (15)	0.0022 (18)	−0.0005 (14)	−0.0025 (16)
C4	0.018 (2)	0.029 (2)	0.0185 (18)	0.0009 (16)	0.0035 (15)	−0.0071 (16)
C5	0.0150 (18)	0.023 (2)	0.0145 (16)	0.0006 (16)	0.0067 (14)	−0.0040 (14)
C6	0.0160 (19)	0.0203 (19)	0.0155 (17)	0.0001 (15)	0.0083 (14)	−0.0019 (14)
C7	0.022 (2)	0.025 (2)	0.0183 (18)	−0.0005 (16)	0.0067 (15)	−0.0053 (15)
C8	0.030 (2)	0.0188 (19)	0.030 (2)	0.0003 (17)	0.0165 (17)	−0.0036 (16)
C9	0.022 (2)	0.024 (2)	0.028 (2)	0.0058 (17)	0.0067 (16)	0.0059 (16)
C10	0.0209 (19)	0.027 (2)	0.0217 (17)	0.0026 (17)	0.0024 (15)	−0.0017 (17)
C11	0.0224 (19)	0.018 (2)	0.0155 (16)	−0.0002 (15)	0.0013 (14)	0.0025 (14)
C12	0.035 (2)	0.018 (2)	0.027 (2)	0.0040 (18)	−0.0033 (18)	0.0004 (16)
C13	0.038 (2)	0.019 (2)	0.030 (2)	−0.0077 (18)	−0.0003 (18)	−0.0021 (16)
C14	0.027 (2)	0.026 (2)	0.0161 (17)	−0.0120 (16)	−0.0017 (15)	−0.0018 (15)
C15	0.0164 (19)	0.026 (2)	0.0117 (16)	−0.0042 (16)	0.0008 (14)	0.0025 (14)
C16	0.020 (2)	0.022 (2)	0.0138 (17)	0.0006 (16)	0.0008 (15)	−0.0029 (15)
C17	0.017 (2)	0.030 (2)	0.0168 (18)	0.0010 (17)	0.0034 (16)	−0.0009 (16)
O5	0.043 (2)	0.037 (2)	0.099 (3)	0.0097 (16)	−0.0277 (18)	−0.0245 (19)

Geometric parameters (Å, º) top

Pd1—N2	1.992 (3)	C4—H4	0.9400
Pd1—O3	2.004 (2)	C5—C6	1.465 (5)
Pd1—N1	2.009 (2)	C6—C7	1.378 (5)
Pd1—N3	2.038 (3)	C7—C8	1.385 (5)
O1—C16	1.238 (4)	C7—H7	0.9400
O2—C16	1.242 (4)	C8—C9	1.378 (5)
O3—C17	1.296 (4)	C8—H8	0.9400
O4—C17	1.225 (4)	C9—C10	1.371 (5)
N1—C1	1.334 (4)	C9—H9	0.9400
N1—C5	1.361 (4)	C10—H10	0.9400
N2—C10	1.337 (4)	C11—C12	1.387 (5)
N2—C6	1.361 (4)	C11—C16	1.538 (5)
N3—C11	1.350 (4)	C12—C13	1.379 (5)
N3—C15	1.354 (4)	C12—H12	0.9400
C1—C2	1.378 (5)	C13—C14	1.386 (5)
C1—H1	0.9400	C13—H13	0.9400
C2—C3	1.376 (5)	C14—C15	1.375 (5)
C2—H2	0.9400	C14—H14	0.9400
C3—C4	1.377 (5)	C15—C17	1.501 (5)
C3—H3	0.9400	O5—H5A	0.8400
C4—C5	1.388 (4)	O5—H5B	0.8400

N2—Pd1—O3	95.44 (10)	C6—C7—C8	119.0 (3)
N2—Pd1—N1	80.21 (12)	C6—C7—H7	120.5
O3—Pd1—N1	169.28 (10)	C8—C7—H7	120.5
N2—Pd1—N3	172.85 (11)	C9—C8—C7	119.4 (3)
O3—Pd1—N3	81.07 (10)	C9—C8—H8	120.3
N1—Pd1—N3	104.28 (11)	C7—C8—H8	120.3
C17—O3—Pd1	112.2 (2)	C10—C9—C8	119.2 (3)
C1—N1—C5	119.5 (3)	C10—C9—H9	120.4
C1—N1—Pd1	125.9 (2)	C8—C9—H9	120.4
C5—N1—Pd1	114.4 (2)	N2—C10—C9	122.0 (3)
C10—N2—C6	119.3 (3)	N2—C10—H10	119.0
C10—N2—Pd1	124.7 (2)	C9—C10—H10	119.0
C6—N2—Pd1	114.8 (2)	N3—C11—C12	119.9 (3)
C11—N3—C15	119.7 (3)	N3—C11—C16	118.7 (3)
C11—N3—Pd1	130.6 (2)	C12—C11—C16	121.0 (3)
C15—N3—Pd1	109.7 (2)	C13—C12—C11	120.5 (4)
N1—C1—C2	121.4 (3)	C13—C12—H12	119.8
N1—C1—H1	119.3	C11—C12—H12	119.8
C2—C1—H1	119.3	C12—C13—C14	118.7 (3)
C3—C2—C1	119.5 (3)	C12—C13—H13	120.6
C3—C2—H2	120.2	C14—C13—H13	120.6
C1—C2—H2	120.2	C15—C14—C13	119.0 (3)
C2—C3—C4	119.6 (3)	C15—C14—H14	120.5
C2—C3—H3	120.2	C13—C14—H14	120.5
C4—C3—H3	120.2	N3—C15—C14	121.7 (3)
C3—C4—C5	118.7 (3)	N3—C15—C17	114.9 (3)
C3—C4—H4	120.6	C14—C15—C17	122.9 (3)
C5—C4—H4	120.6	O1—C16—O2	128.8 (3)
N1—C5—C4	121.0 (3)	O1—C16—C11	115.4 (3)
N1—C5—C6	114.4 (3)	O2—C16—C11	115.7 (3)
C4—C5—C6	124.3 (3)	O4—C17—O3	124.4 (3)
N2—C6—C7	121.1 (3)	O4—C17—C15	120.1 (3)
N2—C6—C5	113.7 (3)	O3—C17—C15	115.4 (3)
C7—C6—C5	125.2 (3)	H5A—O5—H5B	109.1

C5—N1—C1—C2	−2.0 (5)	C8—C9—C10—N2	1.2 (5)
Pd1—N1—C1—C2	−178.4 (3)	C15—N3—C11—C12	−7.2 (5)
N1—C1—C2—C3	−1.6 (5)	Pd1—N3—C11—C12	171.6 (3)
C1—C2—C3—C4	3.2 (5)	C15—N3—C11—C16	166.2 (3)
C2—C3—C4—C5	−1.3 (5)	Pd1—N3—C11—C16	−15.0 (4)
C1—N1—C5—C4	4.0 (5)	N3—C11—C12—C13	2.0 (6)
Pd1—N1—C5—C4	−179.3 (3)	C16—C11—C12—C13	−171.2 (3)
C1—N1—C5—C6	−170.6 (3)	C11—C12—C13—C14	3.1 (6)
Pd1—N1—C5—C6	6.1 (4)	C12—C13—C14—C15	−3.0 (6)
C3—C4—C5—N1	−2.4 (5)	C11—N3—C15—C14	7.3 (5)
C3—C4—C5—C6	171.7 (3)	Pd1—N3—C15—C14	−171.6 (3)
C10—N2—C6—C7	−1.6 (5)	C11—N3—C15—C17	−164.5 (3)
Pd1—N2—C6—C7	166.6 (3)	Pd1—N3—C15—C17	16.5 (3)
C10—N2—C6—C5	176.6 (3)	C13—C14—C15—N3	−2.2 (5)
Pd1—N2—C6—C5	−15.2 (4)	C13—C14—C15—C17	169.0 (3)
N1—C5—C6—N2	5.9 (4)	N3—C11—C16—O1	−28.4 (4)
C4—C5—C6—N2	−168.6 (3)	C12—C11—C16—O1	144.9 (3)
N1—C5—C6—C7	−176.0 (3)	N3—C11—C16—O2	154.0 (3)
C4—C5—C6—C7	9.6 (6)	C12—C11—C16—O2	−32.6 (5)
N2—C6—C7—C8	2.2 (5)	Pd1—O3—C17—O4	163.9 (3)
C5—C6—C7—C8	−175.8 (3)	Pd1—O3—C17—C15	−20.6 (4)
C6—C7—C8—C9	−1.0 (5)	N3—C15—C17—O4	178.1 (3)
C7—C8—C9—C10	−0.6 (5)	C14—C15—C17—O4	6.3 (5)
C6—N2—C10—C9	−0.1 (5)	N3—C15—C17—O3	2.4 (4)
Pd1—N2—C10—C9	−167.0 (3)	C14—C15—C17—O3	−169.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5A···O1ⁱ	0.84	1.96	2.792 (4)	174
O5—H5B···O2ⁱⁱ	0.84	1.99	2.790 (4)	160
C2—H2···O5ⁱⁱⁱ	0.94	2.59	3.460 (5)	154
C3—H3···O2^iv	0.94	2.31	3.245 (4)	173
C4—H4···O1^v	0.94	2.35	3.261 (4)	162
C8—H8···O5^v	0.94	2.47	2.997 (5)	116
C10—H10···O3	0.94	2.55	3.083 (4)	117
C13—H13···O4^vi	0.94	2.43	3.336 (5)	161

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

Acknowledgements

The author thanks the KBSI, Seoul Center, for the X-ray data collection.

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 (grant No. 2018R1D1A1B07050550).

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