1-Benzoyl-3-(5-quinol­yl)thio­urea

Du, W.-H.; Wei, C.-M.; Wang, W.-F.

doi:10.1107/S1600536809000932

organic compounds

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ISSN: 2056-9890

Volume 65| Part 2| February 2009| Page o308

doi:10.1107/S1600536809000932

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1-Benzoyl-3-(5-quinolyl)thiourea

Wen-Hu Du,^a,^b Chang-Mei Wei ^b,^c ^* and Wei-Feng Wang ^a,^b

^aCollege of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, ^bDepartment of Chemistry of Huaiyin Teachers College, Huaian 223300, People's Republic of China, and ^cJangsu Key Laboratory for Chemistry of Low-Dimensional Materials, Huaian 223300, People's Republic of China
^*Correspondence e-mail: wangyyx2008@163.com

(Received 1 December 2008; accepted 8 January 2009; online 14 January 2009)

The title compound, C₁₇H₁₃N₃OS, was obtained by the reaction of benzoyl chloride, ammonium thiocyanate and 5-aminoquinoline in the presence of polyethyleneglycol-400 (PEG-400) as a phase-transfer catalyst. The compound crystallized as discrete molecules linked by N—H⋯N and C—H⋯N hydrogen bonds involving all the potential donors, generating sheets parallel to (100). An intramolecular N—H⋯O bond is also present.

Related literature

For the biological activity of acyl thioureas, see: Hackmann (1960 ); Sarkis & Faisal (1985 ). For their application in the synthesis of supramolecular complexes, see: Pluta & Sadlej (2001 ); Kaminsky et al. (2002 ). For a related structure, see: Xue et al. (2004 ).

Experimental

Crystal data

C₁₇H₁₃N₃OS
M_r = 307.36
Monoclinic, P 2₁ /n
a = 5.0875 (1) Å
b = 16.1718 (4) Å
c = 18.2847 (4) Å
β = 95.892 (2)°
V = 1496.41 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 296 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.939, T_max = 0.969
13322 measured reflections
3411 independent reflections
2184 reflections with I > 2σ(I)
R_int = 0.032
3 standard reflections every 97 reflections intensity decay: 2.1%

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.129
S = 1.04
3411 reflections
207 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H6⋯N3ⁱ	0.825 (17)	2.283 (17)	3.100 (3)	170.5 (18)
N2—H7⋯O1	0.91 (3)	1.84 (3)	2.619 (3)	143 (3)
C6—H5⋯N3ⁱ	0.93	2.46	3.252 (3)	143
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809000932/hg2453sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809000932/hg2453Isup2.hkl

checkCIF report

Comment top

Acyl thioureas have extensive biological activities such as bacteriostasis, weeding (Hackmann, 1960) and plant growth regulating (Sarkis & Faisal, 1985). In addition, acyl thioureas are excellent ligands, and have been widely applied in synthesis of supramolecular complexes (Pluta & Sadlej, 2001; Kaminsky et al., 2002). The title compound, (I) crystallizes as discrete molecules (Fig. 1). The full molecule is a big conjugated system because the bond lengths of C1—C7, C7—N1, C8—N1, C8—N2 and C9—N2 become shorter than standard values, and the bond lengths of C7—O1 and C8—S1 become longer than standard values. In (I) the torsion angle for C17—C9—N2—C8 of -78.2 (3)° indicates the quinoline ring is approximately orthogonal to the rest of the molecule. The molecules in (I) are linked by N1—H6···N3, N2—H7···O1 and C6—H5···N3 hydrogen bonds involving all the potential donors, generating sheets parallel to (100), as shown in Fig. 2. In addition, the bond lengths of S—C (1.655 (2)Å) and O—C(1.223 (2)Å) in (I) are longer than the bond lengths of S—C(1.6503Å) and O—C(1.201Å) in N-(4,6-dimethylpyrimidin-2-ylcarbamothioyl)benzamide (Xue et al., 2004)

Related literature top

For the biological activity of acyl thioureas, see: Hackmann (1960); Sarkis & Faisal (1985). For their application in the synthesis of supramolecular complexes, see: Pluta & Sadlej (2001); Kaminsky et al. (2002). For a related structure, see: Xue et al. (2004).

Experimental top

The title compound was synthesized as following. A mixture of benzoyl chloride (1400 mg, 10 mmol), ammonium thiocyanate (1140 mg, 15 mmol), 5-aminoquinoline (1300 mg, 9 mmol) and dichloromethane (50 ml) in the presence of PEG-400 (1200 mg, 3 mmol) as phase transfer catalyst at room temperature for 8h with stirring. The reaction mixture was evaporated to give a residue. Singles crystals suitable for X-ray analysis were obtained by slow evaporation of a mixture solution of dichloromethane and ethanol.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (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 (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the a axis, showing two layers of molecules connected by van der waals.

1-Benzoyl-3-(5-quinolyl)thiourea top

Crystal data top

C₁₇H₁₃N₃OS	F(000) = 640
M_r = 307.36	D_x = 1.364 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 446.2–446.7 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 5.0875 (1) Å	Cell parameters from 3090 reflections
b = 16.1718 (4) Å	θ = 2.2–22.4°
c = 18.2847 (4) Å	µ = 0.22 mm⁻¹
β = 95.892 (2)°	T = 296 K
V = 1496.41 (6) Å³	Rod, yellow
Z = 4	0.40 × 0.30 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2184 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.032
Graphite monochromator	θ_max = 27.4°, θ_min = 1.7°
ω/2θ scans	h = −6→6
Absorption correction: ψ scan (North et al., 1968)	k = −20→18
T_min = 0.939, T_max = 0.969	l = −23→23
13322 measured reflections	3 standard reflections every 97 reflections
3411 independent reflections	intensity decay: 2.1%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0482P)² + 0.4696P] where P = (F_o² + 2F_c²)/3
3411 reflections	(Δ/σ)_max < 0.001
207 parameters	Δρ_max = 0.30 e Å⁻³
2 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₇H₁₃N₃OS	V = 1496.41 (6) Å³
M_r = 307.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.0875 (1) Å	µ = 0.22 mm⁻¹
b = 16.1718 (4) Å	T = 296 K
c = 18.2847 (4) Å	0.40 × 0.30 × 0.20 mm
β = 95.892 (2)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2184 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.032
T_min = 0.939, T_max = 0.969	3 standard reflections every 97 reflections
13322 measured reflections	intensity decay: 2.1%
3411 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	2 restraints
wR(F²) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.30 e Å⁻³
3411 reflections	Δρ_min = −0.22 e Å⁻³
207 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 > 2sigma(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
S1	−0.00333 (14)	0.14855 (4)	0.20925 (4)	0.0704 (2)
O1	0.5088 (4)	0.09876 (10)	0.02568 (9)	0.0724 (5)
N1	0.2883 (4)	0.17950 (11)	0.10117 (10)	0.0503 (4)
N2	0.2175 (4)	0.04129 (12)	0.12428 (10)	0.0602 (5)
C17	0.2711 (4)	−0.05169 (12)	0.23117 (11)	0.0442 (5)
C13	0.1919 (4)	−0.12237 (12)	0.26802 (11)	0.0482 (5)
C7	0.4431 (5)	0.16753 (13)	0.04478 (11)	0.0524 (5)
N3	0.3173 (4)	−0.14846 (11)	0.33306 (10)	0.0579 (5)
C1	0.5204 (4)	0.24240 (13)	0.00465 (10)	0.0470 (5)
C16	0.4940 (4)	−0.00801 (14)	0.26304 (13)	0.0558 (6)
H13	0.5538	0.0389	0.2404	0.067*
C8	0.1748 (4)	0.11985 (13)	0.14277 (11)	0.0511 (5)
C12	−0.0297 (5)	−0.16872 (13)	0.23615 (14)	0.0582 (6)
H10	−0.0850	−0.2156	0.2597	0.070*
C9	0.1265 (4)	−0.02866 (13)	0.16352 (12)	0.0520 (5)
C11	−0.1587 (5)	−0.14385 (14)	0.17142 (14)	0.0607 (6)
H9	−0.3023	−0.1745	0.1508	0.073*
C2	0.7141 (5)	0.23490 (16)	−0.04248 (13)	0.0650 (6)
H1	0.8019	0.1848	−0.0458	0.078*
C15	0.6203 (5)	−0.03616 (15)	0.32799 (13)	0.0621 (6)
H12	0.7686	−0.0090	0.3502	0.075*
C14	0.5228 (5)	−0.10613 (16)	0.36003 (13)	0.0637 (6)
H11	0.6111	−0.1242	0.4042	0.076*
C6	0.3941 (5)	0.31702 (15)	0.00781 (13)	0.0658 (7)
H5	0.2610	0.3232	0.0386	0.079*
C5	0.4626 (6)	0.38332 (17)	−0.03438 (14)	0.0784 (8)
H4	0.3787	0.4340	−0.0308	0.094*
C4	0.6519 (6)	0.37434 (18)	−0.08094 (14)	0.0747 (7)
H3	0.6947	0.4184	−0.1102	0.090*
C10	−0.0822 (5)	−0.07367 (14)	0.13504 (13)	0.0599 (6)
H8	−0.1754	−0.0578	0.0909	0.072*
C3	0.7785 (5)	0.30086 (19)	−0.08470 (15)	0.0764 (8)
H2	0.9100	0.2950	−0.1161	0.092*
H6	0.268 (4)	0.2277 (10)	0.1143 (10)	0.043 (6)*
H7	0.324 (5)	0.0371 (19)	0.0876 (14)	0.115 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0932 (5)	0.0458 (4)	0.0790 (4)	0.0004 (3)	0.0421 (4)	0.0001 (3)
O1	0.1085 (14)	0.0473 (10)	0.0671 (10)	0.0049 (9)	0.0359 (10)	−0.0030 (8)
N1	0.0701 (12)	0.0363 (10)	0.0461 (10)	0.0012 (9)	0.0131 (9)	0.0013 (8)
N2	0.0852 (15)	0.0426 (11)	0.0558 (12)	0.0015 (10)	0.0220 (11)	0.0056 (9)
C17	0.0501 (11)	0.0343 (10)	0.0503 (11)	0.0001 (9)	0.0159 (9)	−0.0048 (9)
C13	0.0589 (13)	0.0362 (11)	0.0522 (12)	0.0016 (9)	0.0189 (10)	−0.0032 (9)
C7	0.0653 (14)	0.0480 (13)	0.0443 (11)	0.0010 (10)	0.0080 (10)	−0.0033 (9)
N3	0.0709 (13)	0.0490 (11)	0.0550 (11)	0.0006 (10)	0.0123 (10)	0.0033 (9)
C1	0.0554 (12)	0.0489 (12)	0.0368 (10)	−0.0039 (10)	0.0048 (9)	0.0001 (9)
C16	0.0594 (14)	0.0449 (13)	0.0664 (14)	−0.0077 (10)	0.0227 (12)	−0.0067 (11)
C8	0.0664 (14)	0.0387 (12)	0.0493 (11)	0.0025 (10)	0.0108 (10)	0.0039 (9)
C12	0.0687 (15)	0.0393 (12)	0.0692 (15)	−0.0076 (10)	0.0199 (12)	−0.0077 (10)
C9	0.0642 (14)	0.0401 (12)	0.0536 (12)	0.0027 (10)	0.0154 (11)	−0.0035 (10)
C11	0.0597 (14)	0.0515 (14)	0.0711 (15)	−0.0089 (11)	0.0068 (12)	−0.0150 (12)
C2	0.0682 (15)	0.0633 (16)	0.0668 (15)	0.0042 (12)	0.0220 (13)	0.0018 (12)
C15	0.0542 (14)	0.0669 (16)	0.0655 (15)	−0.0073 (12)	0.0077 (12)	−0.0149 (12)
C14	0.0670 (16)	0.0664 (16)	0.0581 (14)	0.0028 (13)	0.0084 (12)	0.0030 (12)
C6	0.0821 (17)	0.0613 (15)	0.0584 (14)	0.0085 (13)	0.0276 (13)	0.0110 (11)
C5	0.104 (2)	0.0613 (16)	0.0740 (16)	0.0143 (15)	0.0295 (16)	0.0208 (13)
C4	0.0806 (18)	0.0751 (19)	0.0706 (16)	−0.0080 (15)	0.0187 (14)	0.0243 (14)
C10	0.0687 (15)	0.0509 (14)	0.0597 (14)	0.0019 (12)	0.0054 (12)	−0.0091 (11)
C3	0.0728 (17)	0.086 (2)	0.0761 (17)	−0.0040 (15)	0.0362 (14)	0.0121 (15)

Geometric parameters (Å, º) top

S1—C8	1.655 (2)	C12—C11	1.354 (3)
O1—C7	1.223 (2)	C12—H10	0.9300
N1—C7	1.374 (3)	C9—C10	1.347 (3)
N1—C8	1.390 (3)	C11—C10	1.391 (3)
N1—H6	0.826 (15)	C11—H9	0.9300
N2—C8	1.338 (3)	C2—C3	1.376 (3)
N2—C9	1.441 (3)	C2—H1	0.9300
N2—H7	0.909 (17)	C15—C14	1.389 (3)
C17—C13	1.407 (3)	C15—H12	0.9300
C17—C16	1.410 (3)	C14—H11	0.9300
C17—C9	1.422 (3)	C6—C5	1.386 (3)
C13—N3	1.358 (3)	C6—H5	0.9300
C13—C12	1.427 (3)	C5—C4	1.357 (4)
C7—C1	1.490 (3)	C5—H4	0.9300
N3—C14	1.304 (3)	C4—C3	1.357 (4)
C1—C6	1.371 (3)	C4—H3	0.9300
C1—C2	1.379 (3)	C10—H8	0.9300
C16—C15	1.369 (3)	C3—H2	0.9300
C16—H13	0.9300

C7—N1—C8	127.96 (19)	C10—C9—N2	120.8 (2)
C7—N1—H6	116.7 (14)	C17—C9—N2	118.35 (19)
C8—N1—H6	115.2 (14)	C12—C11—C10	121.7 (2)
C8—N2—C9	123.42 (19)	C12—C11—H9	119.1
C8—N2—H7	112 (2)	C10—C11—H9	119.1
C9—N2—H7	124 (2)	C3—C2—C1	120.6 (2)
C13—C17—C16	117.8 (2)	C3—C2—H1	119.7
C13—C17—C9	118.79 (19)	C1—C2—H1	119.7
C16—C17—C9	123.39 (19)	C16—C15—C14	118.7 (2)
N3—C13—C17	122.7 (2)	C16—C15—H12	120.6
N3—C13—C12	118.3 (2)	C14—C15—H12	120.6
C17—C13—C12	118.9 (2)	N3—C14—C15	125.1 (2)
O1—C7—N1	122.5 (2)	N3—C14—H11	117.4
O1—C7—C1	120.3 (2)	C15—C14—H11	117.4
N1—C7—C1	117.14 (19)	C1—C6—C5	120.8 (2)
C14—N3—C13	117.0 (2)	C1—C6—H5	119.6
C6—C1—C2	118.1 (2)	C5—C6—H5	119.6
C6—C1—C7	123.1 (2)	C4—C5—C6	120.1 (3)
C2—C1—C7	118.6 (2)	C4—C5—H4	119.9
C15—C16—C17	118.6 (2)	C6—C5—H4	119.9
C15—C16—H13	120.7	C3—C4—C5	119.8 (2)
C17—C16—H13	120.7	C3—C4—H3	120.1
N2—C8—N1	115.68 (19)	C5—C4—H3	120.1
N2—C8—S1	124.54 (17)	C9—C10—C11	120.3 (2)
N1—C8—S1	119.78 (16)	C9—C10—H8	119.9
C11—C12—C13	119.5 (2)	C11—C10—H8	119.9
C11—C12—H10	120.2	C4—C3—C2	120.6 (2)
C13—C12—H10	120.2	C4—C3—H2	119.7
C10—C9—C17	120.8 (2)	C2—C3—H2	119.7

C16—C17—C13—N3	1.5 (3)	C16—C17—C9—C10	178.8 (2)
C9—C17—C13—N3	−179.51 (18)	C13—C17—C9—N2	−176.79 (18)
C16—C17—C13—C12	−178.68 (18)	C16—C17—C9—N2	2.1 (3)
C9—C17—C13—C12	0.3 (3)	C8—N2—C9—C10	105.1 (3)
C8—N1—C7—O1	−2.7 (4)	C8—N2—C9—C17	−78.2 (3)
C8—N1—C7—C1	174.7 (2)	C13—C12—C11—C10	−0.4 (3)
C17—C13—N3—C14	−1.8 (3)	C6—C1—C2—C3	0.3 (3)
C12—C13—N3—C14	178.4 (2)	C7—C1—C2—C3	175.3 (2)
O1—C7—C1—C6	160.1 (2)	C17—C16—C15—C14	−0.4 (3)
N1—C7—C1—C6	−17.3 (3)	C13—N3—C14—C15	1.0 (4)
O1—C7—C1—C2	−14.6 (3)	C16—C15—C14—N3	0.1 (4)
N1—C7—C1—C2	168.0 (2)	C2—C1—C6—C5	−1.0 (4)
C13—C17—C16—C15	−0.4 (3)	C7—C1—C6—C5	−175.7 (2)
C9—C17—C16—C15	−179.3 (2)	C1—C6—C5—C4	1.7 (4)
C9—N2—C8—N1	176.8 (2)	C6—C5—C4—C3	−1.6 (4)
C9—N2—C8—S1	−4.2 (3)	C17—C9—C10—C11	−0.3 (3)
C7—N1—C8—N2	−1.6 (3)	N2—C9—C10—C11	176.3 (2)
C7—N1—C8—S1	179.31 (18)	C12—C11—C10—C9	0.6 (4)
N3—C13—C12—C11	179.8 (2)	C5—C4—C3—C2	0.9 (4)
C17—C13—C12—C11	0.0 (3)	C1—C2—C3—C4	−0.3 (4)
C13—C17—C9—C10	−0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H6···N3ⁱ	0.83 (2)	2.28 (2)	3.100 (3)	171 (2)
N2—H7···O1	0.91 (3)	1.84 (3)	2.619 (3)	143 (3)
C6—H5···N3ⁱ	0.93	2.46	3.252 (3)	143

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃N₃OS
M_r	307.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	5.0875 (1), 16.1718 (4), 18.2847 (4)
β (°)	95.892 (2)
V (Å³)	1496.41 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.939, 0.969
No. of measured, independent and observed [I > 2σ(I)] reflections	13322, 3411, 2184
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.129, 1.04
No. of reflections	3411
No. of parameters	207
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.22

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H6···N3ⁱ	0.825 (17)	2.283 (17)	3.100 (3)	170.5 (18)
N2—H7···O1	0.91 (3)	1.84 (3)	2.619 (3)	143 (3)
C6—H5···N3ⁱ	0.9300	2.4600	3.252 (3)	143.00

Symmetry code: (i) −x+1/2, y+1/2, −z+1/2.

Acknowledgements

We are grateful to the Science Foundation of Jiangsu Education Bureau (05KJD 150039), the Professor Foundation of Huaiyin Teachers College (05 HSJS018) and the Science Foundation of Jangsu Key Laboratory for the Chemistry of Low-Dimensional Materials (JSKC 06028) for financial support.

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