N-Methyl-N-phenyl-2-(quinolin-8-yl­oxy)acetamide monohydrate

Zhi, L.-H.; Wu, W.-N.; Li, S.; Li, Y.-L.; Cai, X.-D.

doi:10.1107/S1600536811017181

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1420

doi:10.1107/S1600536811017181

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N-Methyl-N-phenyl-2-(quinolin-8-yloxy)acetamide monohydrate

Li-Hua Zhi,^a Wei-Na Wu,^a ^* Shu Li,^a Yun-Long Li ^a and Xiao-Dong Cai ^a

^aDepartment of Physics and Chemistry, Henan Polytechnic University, Jiaozuo 454000, People's Republic of China
^*Correspondence e-mail: wuwn08@hpu.edu.cn

(Received 25 April 2011; accepted 6 May 2011; online 14 May 2011)

In the title compound, C₁₈H₁₆N₂O₂·H₂O, the dihedral angle between the quinoline ring system and the benzene ring is 87.19 (8)°. In the crystal, water molecules are linked to acetamide molecules via intermolecular O—H⋯N and O—H⋯O hydrogen bonds.

Related literature

For the luminescent properties of lanthanide complexes with amide-type ligands, see: Li et al. (2003 ); Wu et al. (2008 ). For the synthesis of 2-chloro-N-methyl-N-phenylacetamide, see: Zhi et al. (2011 ). For the similar structure of N-phenyl-2-(quinolin-8-yloxy)acetamide hemihydrate, see: Li et al. (2005 ).

Experimental

Crystal data

C₁₈H₁₆N₂O₂·H₂O
M_r = 310.34
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.6028 (8) Å
b = 14.9207 (18) Å
c = 16.3505 (19) Å
V = 1610.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.16 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.986, T_max = 0.991
10373 measured reflections
3911 independent reflections
3113 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.101
S = 1.05
3911 reflections
217 parameters
125 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WA⋯O2	0.86 (1)	1.97 (1)	2.8249 (19)	178 (3)
O1W—H1WB⋯N1	0.86 (1)	1.97 (1)	2.831 (2)	176 (3)

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); 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); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811017181/vm2091sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017181/vm2091Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017181/vm2091Isup3.cml

checkCIF report

Comment top

The amide type open-chain ligands have attracted much attention mainly because their excellent coordination ability and high selectivity to metal ions. Lanthanide complexes usually exhibit fascinating properties that may have potential applications in biology, medicine, and material science (Li et al., 2003). The luminescent properties of lanthanide complexes with amide type ligands have been investigated in our previous work (Wu et al., 2008). As part of our ongoing studies of the amide type ligands, the title compound was synthesized and characterized by X-ray diffraction.

In the title compound, all bond lengths are comparable with those observed in a similar compound (Li et al., 2005). The dihedral angle between the quinoline ring (N1/C1–C9, r.m.s. deviation 0.0038 Å) and the benzene ring(C13–C18, r.m.s. deviation 0.0049 Å) is 87.19 (8)°. In the crystal structure, solvent water molecules form intermolecular O—H···N and O—H···O hydrogen bonds with acetamide molecules to stabilize the packing (Table 1).

Related literature top

For the luminescent properties of lanthanide complexes with amide-type ligands, see: Li et al. (2003); Wu et al. (2008). For the synthesis of 2-chloro-N-methyl-N-phenylacetamide, see: Zhi et al. (2011). For the similar structure of N-phenyl-2-(quinolin-8-yloxy)acetamide hemihydrate, see: Li et al. (2005).

Experimental top

8-Hydroxyquinoline (1.5 g, 10.3 mmol) and anhydrous potassium carbonate (1.6 g, 11.6 mmol)were added to DMF (15 mL), then 2-chloro-N-methyl-N-phenylacetamide (1.83 g, 10.0 mmol, Zhi et al., 2011) and a small quantity of KI were added. The reaction mixture was stirred for 5 h at 100–110 °C. After cooling down, 150 mL water was added and stirred for 2 h. The precipitate was collected by filtration and washed with water. Recrystallization from EtOH/H₂O (1:1) gave colorless blocks.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with displacement ellipsoids shown at the 50% probability level.

N-Methyl-N-phenyl-2-(quinolin-8-yloxy)acetamide monohydrate top

Crystal data top

C₁₈H₁₆N₂O₂·H₂O	F(000) = 656
M_r = 310.34	D_x = 1.280 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	θ = 1.9–28.2°
a = 6.6028 (8) Å	µ = 0.09 mm⁻¹
b = 14.9207 (18) Å	T = 296 K
c = 16.3505 (19) Å	Block, colorless
V = 1610.8 (3) Å³	0.16 × 0.15 × 0.10 mm
Z = 4

Data collection top

Bruker SMART CCD diffractometer	3911 independent reflections
Radiation source: fine-focus sealed tube	3113 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 28.2°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −8→8
T_min = 0.986, T_max = 0.991	k = −19→18
10373 measured reflections	l = −21→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0498P)² + 0.0847P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.005
3911 reflections	Δρ_max = 0.12 e Å⁻³
217 parameters	Δρ_min = −0.14 e Å⁻³
125 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0132 (19)

Crystal data top

C₁₈H₁₆N₂O₂·H₂O	V = 1610.8 (3) Å³
M_r = 310.34	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.6028 (8) Å	µ = 0.09 mm⁻¹
b = 14.9207 (18) Å	T = 296 K
c = 16.3505 (19) Å	0.16 × 0.15 × 0.10 mm

Data collection top

Bruker SMART CCD diffractometer	3911 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3113 reflections with I > 2σ(I)
T_min = 0.986, T_max = 0.991	R_int = 0.027
10373 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	125 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.12 e Å⁻³
3911 reflections	Δρ_min = −0.14 e Å⁻³
217 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
O1	0.80212 (17)	0.10711 (7)	0.15970 (6)	0.0452 (3)
O2	0.8822 (2)	0.06977 (8)	0.31349 (8)	0.0583 (4)
C8	0.7564 (3)	0.12177 (10)	0.07926 (9)	0.0420 (4)
N2	0.6671 (2)	0.17225 (9)	0.36347 (8)	0.0471 (3)
N1	1.0695 (2)	0.04605 (10)	0.05053 (9)	0.0510 (4)
C10	0.6699 (3)	0.14635 (11)	0.21760 (9)	0.0440 (4)
H10A	0.5345	0.1221	0.2113	0.053*
H10B	0.6637	0.2107	0.2095	0.053*
C11	0.7500 (2)	0.12557 (10)	0.30174 (10)	0.0419 (3)
C9	0.9020 (3)	0.08886 (10)	0.02220 (10)	0.0437 (4)
C13	0.5129 (2)	0.23910 (10)	0.35189 (9)	0.0415 (4)
C7	0.5874 (3)	0.16515 (12)	0.05232 (12)	0.0552 (5)
H7	0.4921	0.1860	0.0896	0.066*
C18	0.5634 (3)	0.32878 (11)	0.35671 (12)	0.0525 (4)
H18	0.6969	0.3456	0.3665	0.063*
C4	0.8680 (3)	0.10316 (12)	−0.06202 (11)	0.0574 (5)
C14	0.3166 (3)	0.21536 (12)	0.33744 (12)	0.0560 (5)
H14	0.2810	0.1551	0.3349	0.067*
C17	0.4168 (3)	0.39294 (12)	0.34698 (13)	0.0596 (5)
H17	0.4515	0.4532	0.3504	0.072*
C2	1.1823 (4)	0.02794 (15)	−0.08759 (13)	0.0711 (5)
H2	1.2811	0.0065	−0.1230	0.085*
C3	1.0166 (4)	0.07026 (13)	−0.11641 (12)	0.0676 (5)
H3	1.0001	0.0778	−0.1725	0.081*
C12	0.7333 (4)	0.15493 (14)	0.44699 (11)	0.0660 (5)
H12A	0.8400	0.1112	0.4465	0.099*
H12B	0.6214	0.1326	0.4785	0.099*
H12C	0.7821	0.2095	0.4710	0.099*
C1	1.2014 (3)	0.01726 (14)	−0.00346 (12)	0.0651 (5)
H1	1.3157	−0.0124	0.0159	0.078*
C15	0.1708 (3)	0.28045 (14)	0.32658 (14)	0.0636 (5)
H15	0.0379	0.2638	0.3153	0.076*
C16	0.2201 (3)	0.36932 (13)	0.33224 (11)	0.0572 (5)
H16	0.1210	0.4131	0.3261	0.069*
C6	0.5576 (4)	0.17827 (13)	−0.03189 (14)	0.0698 (6)
H6	0.4425	0.2084	−0.0497	0.084*
C5	0.6923 (4)	0.14804 (14)	−0.08755 (13)	0.0716 (6)
H5	0.6686	0.1570	−0.1430	0.086*
O1W	1.2156 (2)	0.02723 (13)	0.21238 (9)	0.0780 (5)
H1WA	1.116 (3)	0.039 (2)	0.2438 (12)	0.117*
H1WB	1.175 (4)	0.035 (2)	0.1629 (7)	0.117*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0470 (6)	0.0525 (6)	0.0361 (6)	0.0104 (5)	0.0031 (5)	−0.0040 (5)
O2	0.0599 (8)	0.0629 (7)	0.0521 (7)	0.0214 (7)	0.0033 (6)	0.0043 (6)
C8	0.0488 (9)	0.0365 (7)	0.0408 (8)	−0.0012 (7)	−0.0025 (7)	−0.0026 (6)
N2	0.0526 (8)	0.0498 (7)	0.0388 (7)	0.0069 (7)	−0.0004 (6)	−0.0044 (6)
N1	0.0518 (8)	0.0548 (8)	0.0464 (8)	0.0031 (7)	0.0078 (7)	−0.0076 (7)
C10	0.0421 (8)	0.0464 (8)	0.0434 (9)	0.0066 (7)	0.0034 (7)	−0.0065 (6)
C11	0.0407 (8)	0.0403 (7)	0.0447 (8)	−0.0014 (7)	0.0044 (7)	0.0006 (6)
C9	0.0550 (10)	0.0375 (8)	0.0387 (8)	−0.0057 (7)	0.0012 (7)	−0.0039 (6)
C13	0.0455 (9)	0.0432 (8)	0.0359 (8)	0.0022 (7)	0.0068 (7)	−0.0048 (6)
C7	0.0585 (11)	0.0503 (9)	0.0567 (11)	0.0080 (9)	−0.0105 (9)	−0.0038 (8)
C18	0.0482 (9)	0.0485 (9)	0.0609 (11)	−0.0033 (9)	0.0073 (8)	−0.0083 (8)
C4	0.0805 (12)	0.0517 (9)	0.0399 (9)	−0.0131 (9)	0.0012 (8)	−0.0027 (7)
C14	0.0520 (10)	0.0456 (9)	0.0702 (12)	−0.0054 (8)	0.0062 (9)	−0.0068 (8)
C17	0.0673 (12)	0.0426 (9)	0.0688 (12)	−0.0005 (9)	0.0122 (10)	−0.0021 (8)
C2	0.0772 (12)	0.0777 (11)	0.0583 (10)	−0.0052 (11)	0.0226 (10)	−0.0194 (9)
C3	0.0946 (13)	0.0671 (10)	0.0410 (9)	−0.0168 (10)	0.0102 (9)	−0.0082 (8)
C12	0.0814 (14)	0.0756 (12)	0.0409 (9)	0.0124 (11)	−0.0048 (10)	−0.0004 (8)
C1	0.0650 (11)	0.0710 (10)	0.0594 (10)	0.0011 (10)	0.0170 (9)	−0.0157 (8)
C15	0.0460 (10)	0.0669 (12)	0.0779 (13)	0.0010 (9)	0.0040 (10)	−0.0074 (10)
C16	0.0607 (12)	0.0571 (10)	0.0538 (10)	0.0140 (9)	0.0081 (9)	0.0007 (8)
C6	0.0790 (14)	0.0625 (11)	0.0680 (13)	0.0115 (11)	−0.0239 (11)	0.0068 (10)
C5	0.1004 (17)	0.0673 (12)	0.0472 (11)	−0.0026 (12)	−0.0181 (12)	0.0063 (9)
O1W	0.0531 (8)	0.1216 (12)	0.0594 (8)	0.0265 (9)	−0.0078 (7)	−0.0196 (9)

Geometric parameters (Å, º) top

O1—C8	1.3670 (19)	C4—C3	1.412 (3)
O1—C10	1.4148 (19)	C14—C15	1.379 (3)
O2—C11	1.2217 (19)	C14—H14	0.9300
C8—C7	1.363 (2)	C17—C16	1.367 (3)
C8—C9	1.427 (2)	C17—H17	0.9300
N2—C11	1.343 (2)	C2—C3	1.348 (3)
N2—C13	1.438 (2)	C2—C1	1.391 (3)
N2—C12	1.457 (2)	C2—H2	0.9300
N1—C1	1.312 (2)	C3—H3	0.9300
N1—C9	1.358 (2)	C12—H12A	0.9600
C10—C11	1.506 (2)	C12—H12B	0.9600
C10—H10A	0.9700	C12—H12C	0.9600
C10—H10B	0.9700	C1—H1	0.9300
C9—C4	1.412 (2)	C15—C16	1.368 (3)
C13—C14	1.364 (3)	C15—H15	0.9300
C13—C18	1.381 (2)	C16—H16	0.9300
C7—C6	1.405 (3)	C6—C5	1.350 (3)
C7—H7	0.9300	C6—H6	0.9300
C18—C17	1.371 (3)	C5—H5	0.9300
C18—H18	0.9300	O1W—H1WA	0.855 (10)
C4—C5	1.403 (3)	O1W—H1WB	0.860 (10)

C8—O1—C10	116.19 (12)	C13—C14—H14	119.9
C7—C8—O1	124.58 (15)	C15—C14—H14	119.9
C7—C8—C9	120.25 (15)	C16—C17—C18	120.76 (17)
O1—C8—C9	115.17 (14)	C16—C17—H17	119.6
C11—N2—C13	123.34 (13)	C18—C17—H17	119.6
C11—N2—C12	119.34 (15)	C3—C2—C1	118.3 (2)
C13—N2—C12	117.32 (14)	C3—C2—H2	120.9
C1—N1—C9	117.70 (16)	C1—C2—H2	120.9
O1—C10—C11	108.01 (13)	C2—C3—C4	120.4 (2)
O1—C10—H10A	110.1	C2—C3—H3	119.8
C11—C10—H10A	110.1	C4—C3—H3	119.8
O1—C10—H10B	110.1	N2—C12—H12A	109.5
C11—C10—H10B	110.1	N2—C12—H12B	109.5
H10A—C10—H10B	108.4	H12A—C12—H12B	109.5
O2—C11—N2	121.78 (15)	N2—C12—H12C	109.5
O2—C11—C10	122.34 (14)	H12A—C12—H12C	109.5
N2—C11—C10	115.88 (14)	H12B—C12—H12C	109.5
N1—C9—C4	122.23 (16)	N1—C1—C2	124.6 (2)
N1—C9—C8	119.17 (14)	N1—C1—H1	117.7
C4—C9—C8	118.59 (17)	C2—C1—H1	117.7
C14—C13—C18	119.42 (16)	C16—C15—C14	120.51 (19)
C14—C13—N2	121.02 (15)	C16—C15—H15	119.7
C18—C13—N2	119.55 (15)	C14—C15—H15	119.7
C8—C7—C6	119.84 (19)	C17—C16—C15	119.19 (19)
C8—C7—H7	120.1	C17—C16—H16	120.4
C6—C7—H7	120.1	C15—C16—H16	120.4
C17—C18—C13	119.93 (17)	C5—C6—C7	121.5 (2)
C17—C18—H18	120.0	C5—C6—H6	119.3
C13—C18—H18	120.0	C7—C6—H6	119.3
C5—C4—C9	119.61 (18)	C6—C5—C4	120.24 (19)
C5—C4—C3	123.58 (19)	C6—C5—H5	119.9
C9—C4—C3	116.8 (2)	C4—C5—H5	119.9
C13—C14—C15	120.17 (17)	H1WA—O1W—H1WB	107.3 (16)

C10—O1—C8—C7	−5.0 (2)	C14—C13—C18—C17	0.0 (3)
C10—O1—C8—C9	174.32 (13)	N2—C13—C18—C17	−179.02 (16)
C8—O1—C10—C11	−177.88 (13)	N1—C9—C4—C5	−179.83 (17)
C13—N2—C11—O2	179.28 (15)	C8—C9—C4—C5	−0.7 (2)
C12—N2—C11—O2	−1.2 (2)	N1—C9—C4—C3	0.3 (2)
C13—N2—C11—C10	−0.7 (2)	C8—C9—C4—C3	179.43 (15)
C12—N2—C11—C10	178.81 (16)	C18—C13—C14—C15	0.9 (3)
O1—C10—C11—O2	−12.8 (2)	N2—C13—C14—C15	179.93 (17)
O1—C10—C11—N2	167.15 (14)	C13—C18—C17—C16	−0.2 (3)
C1—N1—C9—C4	−0.3 (2)	C1—C2—C3—C4	0.4 (3)
C1—N1—C9—C8	−179.41 (16)	C5—C4—C3—C2	179.79 (19)
C7—C8—C9—N1	179.84 (15)	C9—C4—C3—C2	−0.4 (3)
O1—C8—C9—N1	0.5 (2)	C9—N1—C1—C2	0.4 (3)
C7—C8—C9—C4	0.7 (2)	C3—C2—C1—N1	−0.4 (3)
O1—C8—C9—C4	−178.61 (14)	C13—C14—C15—C16	−1.7 (3)
C11—N2—C13—C14	77.0 (2)	C18—C17—C16—C15	−0.5 (3)
C12—N2—C13—C14	−102.5 (2)	C14—C15—C16—C17	1.5 (3)
C11—N2—C13—C18	−103.99 (19)	C8—C7—C6—C5	0.6 (3)
C12—N2—C13—C18	76.5 (2)	C7—C6—C5—C4	−0.7 (3)
O1—C8—C7—C6	178.61 (17)	C9—C4—C5—C6	0.7 (3)
C9—C8—C7—C6	−0.7 (3)	C3—C4—C5—C6	−179.47 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2	0.86 (1)	1.97 (1)	2.8249 (19)	178 (3)
O1W—H1WB···N1	0.86 (1)	1.97 (1)	2.831 (2)	176 (3)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆N₂O₂·H₂O
M_r	310.34
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.6028 (8), 14.9207 (18), 16.3505 (19)
V (Å³)	1610.8 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.16 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.986, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	10373, 3911, 3113
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.665

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.101, 1.05
No. of reflections	3911
No. of parameters	217
No. of restraints	125
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.14

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WA···O2	0.855 (10)	1.970 (11)	2.8249 (19)	178 (3)
O1W—H1WB···N1	0.860 (10)	1.972 (11)	2.831 (2)	176 (3)

Acknowledgements

The authors are grateful to the National Natural Science Foundation of China for financial support (grant No. 21001040).

References

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