Aqua­(3-methyl­isoquinoline-κN)silver(I) 4-amino­benzene­sulfonate

Zhang, Y.-M.; Hou, D.-Y.; Li, T.-C.; Xin, G.

doi:10.1107/S1600536807061983

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page m224

https://doi.org/10.1107/S1600536807061983

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Aqua(3-methylisoquinoline-κN)silver(I) 4-aminobenzenesulfonate

Yong-Mei Zhang,^a ^* Dong-Yan Hou,^a Tie-Chun Li ^a and Guang Xin ^a

^aDepartment of Chemistry, Anshan Normal University, Anshan 114007, People's Republic of China
^*Correspondence e-mail: yongmeizhang@yahoo.cn

(Received 6 November 2007; accepted 22 November 2007; online 18 December 2007)

In the title compound, [Ag(C₁₀H₉N)(H₂O)](C₆H₆NO₃S), the Ag^I atom is two-coordinated by one N atom from a 3-methylisoquinoline ligand and one water molecule. The 4-aminobenzenesulfonate counter-anion does not show any bonding interactions with the Ag^I atom. The compound exhibits a three-dimensional supramolecular structure constructed by hydrogen bonds. Adjacent isoquinoline groups form π–π interactions, with a centroid–centroid distance of 3.54 (1) Å. The crystal studied was an inversion twin.

Related literature

For related literature, see: Atria et al. (1994 ); Cai et al. (2003 ); Li et al. (2006 ).

Experimental

Crystal data

[Ag(C₁₀H₉N)(H₂O)](C₆H₆NO₃S)
M_r = 441.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.779 (1) Å
b = 13.997 (3) Å
c = 18.076 (4) Å
V = 1715.2 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.32 mm⁻¹
T = 293 (2) K
0.47 × 0.09 × 0.06 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.529, T_max = 0.911
7289 measured reflections
3904 independent reflections
2458 reflections with I > 2σ(I)
R_int = 0.069

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.117
S = 0.97
3904 reflections
221 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.49 e Å⁻³
Absolute structure: Flack (1983 ), 1646 Friedel pairs
Flack parameter: 0.46 (6)

Table 1
Selected geometric parameters (Å, °)

Ag1—N1	2.137 (4)
Ag1—O1W	2.138 (5)

N1—Ag1—O1W	178.7 (2)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1ⁱ	0.86	2.37	3.092 (6)	142
N2—H2B⋯O3ⁱⁱ	0.86	2.18	3.005 (7)	160
O1W—H36⋯O2ⁱ	0.86 (4)	2.25 (3)	3.027 (8)	150 (6)
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1990 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536807061983/hy2101sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061983/hy2101Isup2.hkl

checkCIF report

Comment top

Sulfonate group can adopt various bridging coordination modes. Silver, a d¹⁰ metal, has no crystal field stabilization energy and hence no dominant geometrical preferences (Li et al., 2006). In this paper, we report the synthesis and crystal structure of a new silver(I) complex with a 4-aminobenzenesulfonate as a counter anion.

As shown in Fig. 1, the sulfonate group in the title compound does not show any bonding interactions with Ag^I atom. Ag^I atom is two-coordinated by one N atom from a neutral 3-methylisoquinoline ligand and one water molecule. Ag1, N1 and O1W are almost co-linear and the N1—Ag1—O1W angle is 179.2 (2)°. The bond distances and angles are normal (Atria et al., 1994; Cai et al., 2003). Furthermore, the compound shows a three-dimensional supramolecular structure constructed by hydrogen bonds. Adjacent isoquinoline groups form π–π interactions with a centroid-to-centroid distance of 3.54 (1) Å.

Related literature top

For related literature, see: Atria et al. (1994); Cai et al. (2003); Li et al. (2006).

Experimental top

A mixture of AgNO₃ (0.170 g, 1 mmol), NaOH (0.040 g, 1 mmol) and 4-aminobenzenesulfonic acid (0.173 g, 1 mmol) in water (15 ml) was stirring for 10 min at room temperature. Then 3-methylisoquinoline (0.143 g, 1 mmol) was added to the solution with stirring for 30 min and a white precipitate was obtained. The precipitate was dissolved by dropwise addition of ammonia (5 M). Green single crystals were obtained by slow evaporation of the solution at room temperature.

Structure description top

For related literature, see: Atria et al. (1994); Cai et al. (2003); Li et al. (2006).

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. H atoms of the water molecule are not shown.

Aqua(3-methylisoquinoline-κN)silver(I) 4-aminobenzenesulfonate top

Crystal data top

[Ag(C₁₀H₉N)(H₂O)](C₆H₆NO₃S)	F(000) = 888
M_r = 441.25	D_x = 1.709 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3904 reflections
a = 6.779 (1) Å	θ = 2.5–27.5°
b = 13.997 (3) Å	µ = 1.32 mm⁻¹
c = 18.076 (4) Å	T = 293 K
V = 1715.2 (6) Å³	Prism, colorless
Z = 4	0.47 × 0.09 × 0.06 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3904 independent reflections
Radiation source: rotation anode	2458 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ω scan	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = 0→8
T_min = 0.529, T_max = 0.911	k = −18→18
7289 measured reflections	l = −23→23

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)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0513P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
3904 reflections	Δρ_max = 0.35 e Å⁻³
221 parameters	Δρ_min = −0.49 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1646 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.46 (6)

Crystal data top

[Ag(C₁₀H₉N)(H₂O)](C₆H₆NO₃S)	V = 1715.2 (6) Å³
M_r = 441.25	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.779 (1) Å	µ = 1.32 mm⁻¹
b = 13.997 (3) Å	T = 293 K
c = 18.076 (4) Å	0.47 × 0.09 × 0.06 mm

Data collection top

Rigaku R-AXIS RAPID diffractometer	3904 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	2458 reflections with I > 2σ(I)
T_min = 0.529, T_max = 0.911	R_int = 0.069
7289 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.117	Δρ_max = 0.35 e Å⁻³
S = 0.97	Δρ_min = −0.49 e Å⁻³
3904 reflections	Absolute structure: Flack (1983), 1646 Friedel pairs
221 parameters	Absolute structure parameter: 0.46 (6)
1 restraint

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

	x	y	z	U_iso*/U_eq
Ag1	0.70457 (8)	0.50911 (3)	1.00258 (3)	0.06244 (18)
C1	0.7687 (8)	0.2835 (3)	0.7059 (3)	0.0348 (12)
C2	0.9238 (9)	0.3384 (4)	0.7295 (4)	0.0427 (14)
H2	1.0520	0.3204	0.7176	0.051*
C3	0.8914 (10)	0.4213 (4)	0.7712 (4)	0.0460 (15)
H3	0.9976	0.4579	0.7872	0.055*
C4	0.6990 (10)	0.4487 (3)	0.7887 (3)	0.0399 (12)
C5	0.5426 (8)	0.3942 (4)	0.7618 (4)	0.0448 (15)
H5	0.4134	0.4130	0.7711	0.054*
C6	0.5789 (8)	0.3121 (4)	0.7212 (4)	0.0442 (15)
H6	0.4734	0.2759	0.7040	0.053*
C7	0.7119 (9)	0.3173 (4)	1.0899 (3)	0.0461 (13)
C8	0.7113 (9)	0.2190 (4)	1.0960 (3)	0.0491 (14)
H8	0.7116	0.1919	1.1430	0.059*
C9	0.7104 (9)	0.1581 (4)	1.0341 (3)	0.0434 (13)
C10	0.7105 (10)	0.0559 (4)	1.0380 (4)	0.0566 (16)
H10	0.7098	0.0257	1.0838	0.068*
C11	0.7118 (10)	0.0041 (4)	0.9762 (4)	0.0633 (17)
H11	0.7126	−0.0622	0.9796	0.076*
C12	0.7120 (11)	0.0471 (4)	0.9061 (4)	0.0596 (16)
H12	0.7111	0.0091	0.8639	0.072*
C13	0.7136 (9)	0.1444 (4)	0.8992 (4)	0.0515 (14)
H13	0.7153	0.1729	0.8528	0.062*
C14	0.7124 (8)	0.2006 (4)	0.9637 (3)	0.0400 (12)
C15	0.7111 (9)	0.3032 (4)	0.9614 (3)	0.0443 (13)
H15	0.7102	0.3326	0.9153	0.053*
C16	0.7102 (11)	0.3833 (5)	1.1546 (4)	0.0719 (19)
H16A	0.7096	0.4482	1.1374	0.108*
H16B	0.8256	0.3725	1.1842	0.108*
H16C	0.5944	0.3718	1.1838	0.108*
N1	0.7112 (7)	0.3582 (3)	1.0203 (3)	0.0427 (11)
N2	0.6671 (7)	0.5272 (3)	0.8343 (3)	0.0530 (13)
H2A	0.5489	0.5431	0.8465	0.064*
H2B	0.7656	0.5599	0.8504	0.064*
O1	0.7523 (6)	0.0984 (2)	0.7042 (3)	0.0573 (13)
O2	0.6892 (9)	0.1821 (3)	0.5914 (2)	0.0673 (13)
O3	1.0187 (7)	0.1748 (3)	0.6393 (3)	0.0701 (15)
O1W	0.7047 (8)	0.6603 (3)	0.9857 (3)	0.0828 (15)
S1	0.8103 (2)	0.17638 (8)	0.65704 (8)	0.0415 (3)
H36	0.593 (5)	0.685 (4)	0.974 (4)	0.099*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ag1	0.0663 (3)	0.0474 (2)	0.0736 (4)	−0.0021 (2)	0.0064 (3)	−0.0002 (3)
C1	0.040 (3)	0.030 (2)	0.035 (3)	0.000 (2)	−0.001 (2)	0.0032 (19)
C2	0.039 (3)	0.048 (3)	0.041 (4)	0.004 (3)	−0.001 (3)	0.000 (3)
C3	0.049 (3)	0.038 (3)	0.051 (4)	−0.005 (3)	−0.010 (3)	−0.005 (3)
C4	0.053 (3)	0.038 (2)	0.029 (3)	0.003 (3)	0.001 (3)	0.000 (2)
C5	0.037 (3)	0.048 (3)	0.050 (4)	0.002 (3)	0.006 (3)	0.001 (3)
C6	0.040 (3)	0.039 (3)	0.053 (4)	−0.005 (3)	−0.003 (3)	−0.003 (3)
C7	0.033 (3)	0.072 (3)	0.034 (3)	0.000 (3)	−0.001 (3)	0.002 (3)
C8	0.044 (3)	0.069 (3)	0.034 (3)	0.003 (3)	0.001 (3)	0.015 (3)
C9	0.033 (2)	0.048 (3)	0.049 (4)	0.003 (3)	−0.002 (3)	0.015 (2)
C10	0.053 (3)	0.052 (3)	0.065 (5)	0.000 (4)	−0.002 (4)	0.022 (3)
C11	0.058 (3)	0.046 (3)	0.086 (5)	0.000 (4)	−0.001 (4)	0.005 (3)
C12	0.059 (4)	0.061 (3)	0.059 (5)	0.002 (4)	−0.004 (4)	−0.015 (3)
C13	0.042 (3)	0.065 (3)	0.048 (4)	0.000 (3)	−0.003 (4)	0.001 (3)
C14	0.028 (2)	0.050 (3)	0.041 (3)	−0.002 (3)	−0.005 (3)	0.007 (2)
C15	0.041 (3)	0.048 (3)	0.043 (4)	−0.005 (3)	0.000 (3)	0.014 (3)
C16	0.066 (4)	0.094 (4)	0.056 (5)	0.001 (4)	0.007 (5)	−0.030 (4)
N1	0.033 (2)	0.053 (2)	0.041 (3)	−0.003 (2)	−0.002 (3)	0.0053 (19)
N2	0.061 (3)	0.047 (2)	0.051 (3)	−0.001 (2)	0.009 (3)	−0.015 (2)
O1	0.082 (4)	0.0380 (17)	0.052 (3)	−0.0009 (19)	0.004 (2)	0.0096 (16)
O2	0.108 (4)	0.051 (2)	0.043 (3)	0.007 (3)	−0.021 (3)	−0.0049 (18)
O3	0.057 (3)	0.054 (2)	0.099 (5)	0.002 (2)	0.030 (3)	−0.018 (2)
O1W	0.104 (4)	0.065 (2)	0.080 (4)	0.010 (3)	−0.009 (4)	−0.014 (3)
S1	0.0534 (8)	0.0328 (6)	0.0383 (8)	0.0019 (7)	0.0015 (8)	−0.0011 (5)

Geometric parameters (Å, º) top

Ag1—N1	2.137 (4)	C10—C11	1.331 (9)
Ag1—O1W	2.138 (5)	C10—H10	0.9300
C1—C2	1.370 (7)	C11—C12	1.403 (9)
C1—C6	1.376 (8)	C11—H11	0.9300
C1—S1	1.762 (5)	C12—C13	1.367 (8)
C2—C3	1.402 (8)	C12—H12	0.9300
C2—H2	0.9300	C13—C14	1.406 (8)
C3—C4	1.396 (9)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.437 (7)
C4—N2	1.390 (6)	C15—N1	1.312 (7)
C4—C5	1.393 (8)	C15—H15	0.9300
C5—C6	1.386 (8)	C16—H16A	0.9600
C5—H5	0.9300	C16—H16B	0.9600
C6—H6	0.9300	C16—H16C	0.9600
C7—C8	1.380 (7)	N2—H2A	0.8600
C7—N1	1.383 (7)	N2—H2B	0.8600
C7—C16	1.490 (8)	O1—S1	1.440 (4)
C8—C9	1.406 (8)	O2—S1	1.445 (5)
C8—H8	0.9300	O3—S1	1.449 (5)
C9—C14	1.405 (8)	O1W—H36	0.86 (4)
C9—C10	1.431 (7)

N1—Ag1—O1W	178.7 (2)	C12—C11—H11	119.2
C2—C1—C6	119.4 (5)	C13—C12—C11	120.7 (6)
C2—C1—S1	120.7 (4)	C13—C12—H12	119.7
C6—C1—S1	119.9 (4)	C11—C12—H12	119.7
C1—C2—C3	120.8 (5)	C12—C13—C14	118.8 (6)
C1—C2—H2	119.6	C12—C13—H13	120.6
C3—C2—H2	119.6	C14—C13—H13	120.6
C4—C3—C2	119.7 (5)	C9—C14—C13	120.9 (5)
C4—C3—H3	120.1	C9—C14—C15	116.7 (5)
C2—C3—H3	120.1	C13—C14—C15	122.4 (5)
N2—C4—C5	121.4 (6)	N1—C15—C14	124.2 (5)
N2—C4—C3	119.8 (5)	N1—C15—H15	117.9
C5—C4—C3	118.7 (5)	C14—C15—H15	117.9
C6—C5—C4	120.3 (5)	C7—C16—H16A	109.5
C6—C5—H5	119.9	C7—C16—H16B	109.5
C4—C5—H5	119.9	H16A—C16—H16B	109.5
C1—C6—C5	120.9 (5)	C7—C16—H16C	109.5
C1—C6—H6	119.5	H16A—C16—H16C	109.5
C5—C6—H6	119.5	H16B—C16—H16C	109.5
C8—C7—N1	119.0 (5)	C15—N1—C7	119.7 (4)
C8—C7—C16	123.8 (6)	C15—N1—Ag1	117.3 (4)
N1—C7—C16	117.2 (5)	C7—N1—Ag1	123.0 (4)
C7—C8—C9	122.8 (5)	C4—N2—H2A	120.0
C7—C8—H8	118.6	C4—N2—H2B	120.0
C9—C8—H8	118.6	H2A—N2—H2B	120.0
C14—C9—C8	117.6 (4)	Ag1—O1W—H36	116 (4)
C14—C9—C10	117.8 (6)	O1—S1—O2	111.9 (3)
C8—C9—C10	124.6 (6)	O1—S1—O3	112.7 (3)
C11—C10—C9	120.2 (6)	O2—S1—O3	111.9 (4)
C11—C10—H10	119.9	O1—S1—C1	107.7 (2)
C9—C10—H10	119.9	O2—S1—C1	105.9 (2)
C10—C11—C12	121.5 (5)	O3—S1—C1	106.3 (2)
C10—C11—H11	119.2

C6—C1—C2—C3	2.4 (9)	C10—C9—C14—C13	0.3 (9)
S1—C1—C2—C3	−177.1 (5)	C8—C9—C14—C15	−1.3 (9)
C1—C2—C3—C4	−0.4 (9)	C10—C9—C14—C15	179.7 (6)
C2—C3—C4—N2	175.7 (5)	C12—C13—C14—C9	0.2 (10)
C2—C3—C4—C5	−2.3 (9)	C12—C13—C14—C15	−179.1 (6)
N2—C4—C5—C6	−175.1 (6)	C9—C14—C15—N1	1.1 (10)
C3—C4—C5—C6	2.8 (9)	C13—C14—C15—N1	−179.6 (6)
C2—C1—C6—C5	−1.9 (9)	C14—C15—N1—C7	−0.2 (9)
S1—C1—C6—C5	177.7 (5)	C14—C15—N1—Ag1	−179.1 (5)
C4—C5—C6—C1	−0.8 (9)	C8—C7—N1—C15	−0.4 (9)
N1—C7—C8—C9	0.1 (10)	C16—C7—N1—C15	−179.5 (7)
C16—C7—C8—C9	179.1 (6)	C8—C7—N1—Ag1	178.4 (4)
C7—C8—C9—C14	0.8 (10)	C16—C7—N1—Ag1	−0.7 (8)
C7—C8—C9—C10	179.7 (7)	C2—C1—S1—O1	111.1 (5)
C14—C9—C10—C11	−0.3 (10)	C6—C1—S1—O1	−68.4 (5)
C8—C9—C10—C11	−179.2 (7)	C2—C1—S1—O2	−129.0 (5)
C9—C10—C11—C12	−0.3 (11)	C6—C1—S1—O2	51.5 (6)
C10—C11—C12—C13	0.9 (11)	C2—C1—S1—O3	−9.8 (6)
C11—C12—C13—C14	−0.8 (11)	C6—C1—S1—O3	170.7 (5)
C8—C9—C14—C13	179.4 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.37	3.092 (6)	142
N2—H2B···O3ⁱⁱ	0.86	2.18	3.005 (7)	160
O1W—H36···O2ⁱ	0.86 (4)	2.25 (3)	3.027 (8)	150 (6)

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

Experimental details

Crystal data
Chemical formula	[Ag(C₁₀H₉N)(H₂O)](C₆H₆NO₃S)
M_r	441.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	6.779 (1), 13.997 (3), 18.076 (4)
V (Å³)	1715.2 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.32
Crystal size (mm)	0.47 × 0.09 × 0.06

Data collection
Diffractometer	Rigaku R-AXIS RAPID
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.529, 0.911
No. of measured, independent and observed [I > 2σ(I)] reflections	7289, 3904, 2458
R_int	0.069
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.117, 0.97
No. of reflections	3904
No. of parameters	221
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.49
Absolute structure	Flack (1983), 1646 Friedel pairs
Absolute structure parameter	0.46 (6)

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Siemens, 1990).

Selected geometric parameters (Å, º) top

Ag1—N1	2.137 (4)	Ag1—O1W	2.138 (5)

N1—Ag1—O1W	178.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1ⁱ	0.86	2.37	3.092 (6)	142
N2—H2B···O3ⁱⁱ	0.86	2.18	3.005 (7)	160
O1W—H36···O2ⁱ	0.86 (4)	2.25 (3)	3.027 (8)	150 (6)

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

Acknowledgements

The authors thank Anshan Normal University for supporting this work.

References

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