Bis(2,2′-bipyridine N,N′-dioxide)bis­(tri­cyano­methanido)manganese(II)

Luo, J.; Yang, F.; Qiu, L.-J.; Wang, X.-X.; Liu, B.-S.

doi:10.1107/S1600536809013828

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Pages m547-m548

doi:10.1107/S1600536809013828

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Bis(2,2′-bipyridine N,N′-dioxide)bis(tricyanomethanido)manganese(II)

Jun Luo,^a Feng Yang,^a ^* Li-Juan Qiu,^a Xin-Xia Wang ^b and Bao-Shu Liu ^a

^aSchool of Pharmacy, Second Military Medical University, Shanghai 200433, People's Republic of China, and ^bDepartment of Pharmacy, Eastern Hepatobiliary Surgery Hospital, Second Military Medical University, Shanghai 200438, People's Republic of China
^*Correspondence e-mail: yangfeng1008@sohu.com

(Received 6 April 2009; accepted 13 April 2009; online 22 April 2009)

In the title complex, [Mn(C₄N₃)₂(C₁₀H₈N₂O₂)₂], the Mn^II atom lies on an inversion center and is coordinated by two 2,2′-bipyridine N,N′-dioxide (dpdo) molecules and two tricyanomethanide (tcm) ligands to form a distorted octahedral geometry. Weak intermolecular C—H⋯O or C—H⋯N hydrogen bonds, involving either the O atom of the dpdo molecule and the pyridyl H atom, or the N atom of the tcm anion and the pyridyl H atom, result in the formation of a three-dimensional network structure.

Related literature

For studies of other coordination polymers constructed with tcm, exhibiting a variety of structures, see: Batten & Murray (2003 ); Miller & Manson (2001 ); Feyerherm et al. (2003 , 2004 ); Abrahams et al. (2003 ); Manson et al. (1998 , 2000 ); Hoshino et al. (1999 ); Batten et al. (1998 , 1999 , 2000 ); Manson & Schlueter (2004 ). For work on manganese–nitroxide complexes, see: Liu et al. (2001 ).

Experimental

Crystal data

[Mn(C₄N₃)₂(C₁₀H₈N₂O₂)₂]
M_r = 611.45
Monoclinic, P 2₁ /c
a = 11.514 (4) Å
b = 16.101 (5) Å
c = 7.143 (2) Å
β = 94.375 (4)°
V = 1320.4 (7) Å³
Z = 2
Mo Kα radiation
μ = 0.56 mm⁻¹
T = 293 K
0.20 × 0.16 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.893, T_max = 0.937
6266 measured reflections
2834 independent reflections
1969 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.071
S = 0.90
2834 reflections
196 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1ⁱ	0.93	2.43	3.350 (2)	171
C10—H10⋯N4ⁱⁱ	0.93	2.53	3.212 (3)	130
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT-Plus (Bruker, 2000); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013828/dn2445sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013828/dn2445Isup2.hkl

checkCIF report

Comment top

Coordination polymers constructed by tricyanomethanide (tcm) have attracted considerable interest due to their diverse structures and fascinating magnetic properties (Batten & Murray, 2003; Miller & Manson, 2001; Feyerherm et al., 2003). Notably, except a doubly interpenetrated (6,3) sheet was observed in Ag(tcm)₂ (Abrahams et al., 2003), most binary tcm complexes display a rutile-like structure (Manson et al., 2000, 1998; Hoshino et al., 1999; Feyerherm et al., 2004). To gain insight into the influence of the coligands on the structures and magnetic properties of tcm complexes, some coligands such as hexamethylenetetramine, 4,4-bipyridyl, 1,2-bi(4-pyridyl)ethane were introduced to the binary tcm systems. Among the Cu^I or Cd^II tcm complexes with these coligands, numerous structure types range from doubly interpenetrated (4,4) sheet to three-dimensional rutile networks were observed (Batten et al., 2000, 1998). By contrast, modification of the Mn^II–tcm binary system with 4,4-bipyridyl as coligands leads to the formation of a one-dimensional chain-like structure (Manson & Schlueter, 2004). On the other hand, 2,2'-dipyridyl N,N'-dioxide (dpdo) is a novel coligand and has two potential oxygen donor atoms. However, no tcm complexes with dpdo as coligand have ever been reported. During our systematic investigation of the nature of dpdo coligand on the structures and properties of tcm complexes, we obtained a new tcm complex with dpdo as coligand, we herein report the synthesis and crystal structure of the new tricyanomethanide complex Mn(dpdo)₂(C₄N₃)₂ (I).

The Mn atom which lies on an inversion center displays an octahedral geometry in which the equatorial plane is formed by four O atoms (O1, O2, O1ⁱ, O2ⁱ) of the dpdo molecules, and the apical sites are occupied by two N atom (N3, N3ⁱ) of the tcm ligands (Fig. 1). The Mn—O(dpdo) distances are in the range from 2.1290 (13) Å to 2.1780 (13) Å, these value are comparable to the corresponding distances in manganese–nitroxide complexes (Liu et al., 2001). The Mn—N(tcm) distances are from 2.2336 (17) Å to 2.2337 (17) Å, and the data are similar to the corresponding distances observed in manganese tcm complex (Batten et al., 1999). Each tricyanomethanide moiety is almost planar. Bond distances and bond angles within the anions are in good agreement with those found in other tricyanomethanide complexes (Hoshino et al., 1999; Batten et al., 1999).

Weak intermolecular C—H···O or C—H···N hydrogen bonds involving either the O atom of the dpdo molecule and the pyridyl H atom or the N atom of the tcm anion and the pyridyl H atom, result in the formation of a three-dimensional network structure (Table 1, Fig. 2).

Related literature top

For studies of other coordination polymers constructed with tcm, exhibiting a variety of structures, see: Batten & Murray (2003); Miller & Manson (2001); Feyerherm et al. (2003, 2004); Abrahams et al. (2003); Manson et al. (1998, 2000); Hoshino et al. (1999); Batten et al. (1998, 1999, 2000); Manson & Schlueter (2004). For work on manganese–nitroxide complexes, see: Liu et al. (2001). [Please check rephrasing]

Experimental top

A 5 ml warm ethanol solution of 2,2'-dipyridyl N,N'-dioxide (0.10 mmol, 18.82 mg) and a 2 ml aqueous colorless solution of manganese nitrate (0.10 mmol, 25.10 mg) were mixed and stirred for 5 min, the mixed solution was yellow. To the mixture was added a 3 ml ethanol–water solution (EtOH:H₂O = 2:1, v/v) of potassium tricyanomethanide (0.20 mmol, 25.83 mg). After stirred for another 5 min, the yellow solution was filtered and the filtrate was slowly evaporated in air. After two week, yellow block crystals of I were isolated in 34% yield. Anal: Calculated for C28H16MnN10O4: C 55.00%, H 2.64%, N 22.91%. Found C 55.16%, H 2.73%, N 23.03%.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the mononuclear structure in (I), showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry code: (i) -x + 1, -y + 1, -z + 1.]
	Fig. 2. Partial packing view showing the formation of the C—H···O and C—H···N hydrogen-bond interactions. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry codes: (i) x, -y + 1/2, z + 1/2; (ii) x - 1, y, z.]

Bis(2,2'-bipyridine N,N'-dioxide)bis(tricyanomethanido)manganese(II) top

Crystal data top

[Mn(C₄N₃)₂(C₁₀H₈N₂O₂)₂]	F(000) = 622
M_r = 611.45	D_x = 1.538 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 954 reflections
a = 11.514 (4) Å	θ = 3.1–24.8°
b = 16.101 (5) Å	µ = 0.56 mm⁻¹
c = 7.143 (2) Å	T = 293 K
β = 94.375 (4)°	Block, yellow
V = 1320.4 (7) Å³	0.20 × 0.16 × 0.10 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	2834 independent reflections
Radiation source: fine-focus sealed tube	1969 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
T_min = 0.893, T_max = 0.937	k = −20→20
6266 measured reflections	l = −5→8

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 0.90	w = 1/[σ²(F_o²) + (0.0269P)²] where P = (F_o² + 2F_c²)/3
2834 reflections	(Δ/σ)_max < 0.001
196 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Mn(C₄N₃)₂(C₁₀H₈N₂O₂)₂]	V = 1320.4 (7) Å³
M_r = 611.45	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.514 (4) Å	µ = 0.56 mm⁻¹
b = 16.101 (5) Å	T = 293 K
c = 7.143 (2) Å	0.20 × 0.16 × 0.10 mm
β = 94.375 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2834 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1969 reflections with I > 2σ(I)
T_min = 0.893, T_max = 0.937	R_int = 0.034
6266 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 0.90	Δρ_max = 0.28 e Å⁻³
2834 reflections	Δρ_min = −0.35 e Å⁻³
196 parameters

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.

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
Mn1	0.5000	0.5000	0.5000	0.02993 (12)
N1	0.64563 (12)	0.36945 (9)	0.7192 (2)	0.0332 (4)
N2	0.41397 (12)	0.43113 (9)	0.8531 (2)	0.0295 (3)
N3	0.67180 (13)	0.55973 (10)	0.5796 (2)	0.0455 (4)
N4	1.03850 (17)	0.50470 (13)	0.7829 (3)	0.0790 (7)
N5	0.96600 (16)	0.72092 (13)	0.4362 (3)	0.0662 (6)
O1	0.57417 (10)	0.37808 (7)	0.56602 (18)	0.0372 (3)
O2	0.46743 (10)	0.49721 (7)	0.78936 (16)	0.0324 (3)
C1	0.76219 (16)	0.36510 (12)	0.7024 (3)	0.0438 (5)
H1	0.7909	0.3727	0.5854	0.053*
C2	0.83767 (17)	0.34971 (12)	0.8549 (4)	0.0508 (6)
H2	0.9172	0.3464	0.8412	0.061*
C3	0.79652 (17)	0.33917 (12)	1.0283 (3)	0.0476 (5)
H3	0.8473	0.3280	1.1327	0.057*
C4	0.67888 (16)	0.34541 (11)	1.0448 (3)	0.0413 (5)
H4	0.6499	0.3388	1.1619	0.050*
C5	0.60310 (15)	0.36128 (10)	0.8902 (3)	0.0326 (4)
C6	0.47602 (15)	0.36233 (11)	0.9049 (3)	0.0306 (4)
C7	0.42058 (17)	0.29644 (12)	0.9818 (3)	0.0407 (5)
H7	0.4629	0.2493	1.0191	0.049*
C8	0.30314 (17)	0.29968 (13)	1.0040 (3)	0.0456 (5)
H8	0.2659	0.2555	1.0580	0.055*
C9	0.24191 (16)	0.36896 (12)	0.9453 (3)	0.0416 (5)
H9	0.1621	0.3716	0.9566	0.050*
C10	0.29796 (15)	0.43425 (12)	0.8701 (3)	0.0356 (5)
H10	0.2560	0.4812	0.8304	0.043*
C11	0.88681 (16)	0.59756 (12)	0.6110 (3)	0.0400 (5)
C12	0.76883 (17)	0.57701 (12)	0.5935 (3)	0.0375 (5)
C13	0.96832 (18)	0.54529 (14)	0.7082 (3)	0.0510 (6)
C14	0.92869 (16)	0.66597 (14)	0.5135 (3)	0.0457 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Mn1	0.0255 (2)	0.0319 (2)	0.0322 (2)	−0.00346 (17)	0.00101 (17)	0.00237 (19)
N1	0.0290 (8)	0.0270 (8)	0.0434 (10)	0.0017 (7)	0.0015 (8)	−0.0001 (7)
N2	0.0299 (8)	0.0302 (9)	0.0283 (8)	−0.0011 (7)	0.0022 (7)	0.0002 (7)
N3	0.0343 (9)	0.0523 (11)	0.0488 (11)	−0.0114 (8)	−0.0041 (8)	0.0086 (9)
N4	0.0531 (12)	0.0831 (16)	0.0977 (18)	0.0124 (12)	−0.0146 (12)	0.0026 (14)
N5	0.0501 (12)	0.0682 (14)	0.0823 (16)	−0.0136 (10)	0.0188 (11)	0.0018 (12)
O1	0.0382 (7)	0.0355 (7)	0.0373 (8)	0.0019 (6)	−0.0017 (6)	−0.0017 (6)
O2	0.0357 (7)	0.0273 (7)	0.0346 (7)	−0.0034 (6)	0.0051 (6)	0.0036 (6)
C1	0.0307 (11)	0.0434 (12)	0.0586 (14)	0.0050 (9)	0.0128 (11)	0.0003 (11)
C2	0.0276 (10)	0.0438 (13)	0.0807 (18)	0.0037 (9)	0.0020 (12)	0.0016 (12)
C3	0.0373 (12)	0.0405 (12)	0.0627 (15)	0.0046 (9)	−0.0111 (11)	0.0025 (11)
C4	0.0406 (12)	0.0356 (11)	0.0469 (13)	0.0032 (9)	−0.0019 (10)	0.0042 (10)
C5	0.0317 (10)	0.0250 (10)	0.0410 (12)	0.0016 (8)	0.0020 (9)	0.0013 (9)
C6	0.0296 (9)	0.0294 (10)	0.0324 (11)	0.0008 (8)	0.0002 (8)	0.0029 (8)
C7	0.0409 (11)	0.0327 (11)	0.0481 (13)	−0.0008 (9)	0.0019 (10)	0.0098 (10)
C8	0.0415 (12)	0.0456 (13)	0.0502 (13)	−0.0103 (10)	0.0081 (11)	0.0087 (11)
C9	0.0291 (10)	0.0533 (13)	0.0430 (12)	−0.0048 (10)	0.0074 (9)	−0.0001 (11)
C10	0.0288 (10)	0.0435 (12)	0.0346 (11)	0.0061 (9)	0.0018 (9)	−0.0014 (9)
C11	0.0265 (10)	0.0460 (12)	0.0473 (13)	−0.0047 (9)	0.0019 (9)	−0.0035 (10)
C12	0.0376 (11)	0.0382 (12)	0.0360 (12)	−0.0024 (9)	−0.0011 (9)	−0.0021 (9)
C13	0.0349 (12)	0.0564 (14)	0.0612 (16)	−0.0020 (11)	0.0008 (11)	−0.0109 (12)
C14	0.0249 (10)	0.0566 (15)	0.0558 (15)	−0.0023 (10)	0.0056 (10)	−0.0099 (12)

Geometric parameters (Å, º) top

Mn1—O2	2.1291 (13)	C2—H2	0.9300
Mn1—O2ⁱ	2.1291 (13)	C3—C4	1.372 (3)
Mn1—O1ⁱ	2.1780 (13)	C3—H3	0.9300
Mn1—O1	2.1780 (13)	C4—C5	1.378 (3)
Mn1—N3ⁱ	2.2337 (17)	C4—H4	0.9300
Mn1—N3	2.2337 (17)	C5—C6	1.475 (2)
N1—O1	1.3252 (19)	C6—C7	1.374 (2)
N1—C5	1.356 (2)	C7—C8	1.374 (3)
N1—C1	1.358 (2)	C7—H7	0.9300
N2—O2	1.3269 (16)	C8—C9	1.368 (3)
N2—C10	1.351 (2)	C8—H8	0.9300
N2—C6	1.354 (2)	C9—C10	1.365 (2)
N3—C12	1.148 (2)	C9—H9	0.9300
N4—C13	1.140 (3)	C10—H10	0.9300
N5—C14	1.144 (2)	C11—C12	1.394 (2)
C1—C2	1.363 (3)	C11—C13	1.404 (3)
C1—H1	0.9300	C11—C14	1.408 (3)
C2—C3	1.370 (3)

O2—Mn1—O2ⁱ	180.0	C2—C3—C4	118.7 (2)
O2—Mn1—O1ⁱ	97.70 (4)	C2—C3—H3	120.6
O2ⁱ—Mn1—O1ⁱ	82.30 (4)	C4—C3—H3	120.6
O2—Mn1—O1	82.30 (4)	C3—C4—C5	120.9 (2)
O2ⁱ—Mn1—O1	97.70 (4)	C3—C4—H4	119.6
O1ⁱ—Mn1—O1	180.0	C5—C4—H4	119.6
O2—Mn1—N3ⁱ	91.14 (5)	N1—C5—C4	119.32 (16)
O2ⁱ—Mn1—N3ⁱ	88.86 (5)	N1—C5—C6	119.42 (17)
O1ⁱ—Mn1—N3ⁱ	90.45 (6)	C4—C5—C6	121.05 (18)
O1—Mn1—N3ⁱ	89.55 (6)	N2—C6—C7	119.30 (16)
O2—Mn1—N3	88.86 (5)	N2—C6—C5	119.70 (15)
O2ⁱ—Mn1—N3	91.14 (5)	C7—C6—C5	120.87 (17)
O1ⁱ—Mn1—N3	89.55 (6)	C6—C7—C8	120.52 (18)
O1—Mn1—N3	90.45 (6)	C6—C7—H7	119.7
N3ⁱ—Mn1—N3	180.00 (8)	C8—C7—H7	119.7
O1—N1—C5	120.64 (14)	C9—C8—C7	118.95 (18)
O1—N1—C1	119.20 (17)	C9—C8—H8	120.5
C5—N1—C1	120.09 (17)	C7—C8—H8	120.5
O2—N2—C10	119.25 (14)	C10—C9—C8	120.03 (18)
O2—N2—C6	120.05 (14)	C10—C9—H9	120.0
C10—N2—C6	120.68 (15)	C8—C9—H9	120.0
C12—N3—Mn1	164.42 (17)	N2—C10—C9	120.47 (18)
N1—O1—Mn1	118.80 (10)	N2—C10—H10	119.8
N2—O2—Mn1	118.06 (10)	C9—C10—H10	119.8
N1—C1—C2	120.8 (2)	C12—C11—C13	120.78 (19)
N1—C1—H1	119.6	C12—C11—C14	120.63 (18)
C2—C1—H1	119.6	C13—C11—C14	118.19 (17)
C1—C2—C3	120.09 (19)	N3—C12—C11	179.7 (2)
C1—C2—H2	120.0	N4—C13—C11	176.8 (2)
C3—C2—H2	120.0	N5—C14—C11	178.0 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱⁱ	0.93	2.43	3.350 (2)	171
C10—H10···N4ⁱⁱⁱ	0.93	2.53	3.212 (3)	130

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

Experimental details

Crystal data
Chemical formula	[Mn(C₄N₃)₂(C₁₀H₈N₂O₂)₂]
M_r	611.45
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.514 (4), 16.101 (5), 7.143 (2)
β (°)	94.375 (4)
V (Å³)	1320.4 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.56
Crystal size (mm)	0.20 × 0.16 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.893, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	6266, 2834, 1969
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.071, 0.90
No. of reflections	2834
No. of parameters	196
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.35

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O1ⁱ	0.93	2.43	3.350 (2)	171.3
C10—H10···N4ⁱⁱ	0.93	2.53	3.212 (3)	130.4

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

Acknowledgements

This project was supported by the National Natural Science Foundation of China (grant No. 20571086).

References

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