3-(1H-Tetra­zol-5-yl)pyridinium 3-(2H-tetra­zol-5-yl)pyridinium dinitrate

Cui, L.-J.

doi:10.1107/S160053680901839X

organic compounds

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Volume 65| Part 7| July 2009| Page o1684

doi:10.1107/S160053680901839X

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3-(1H-Tetrazol-5-yl)pyridinium 3-(2H-tetrazol-5-yl)pyridinium dinitrate

Li-Jing Cui ^a ^*

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: fudavid88@yahoo.com.cn

(Received 7 April 2009; accepted 15 May 2009; online 27 June 2009)

In the title compound, C₆H₆N₅⁺·NO₃⁻, there are two different isomers of the cation within the asymmetric unit. The dihedral angles between the the pyridinium and tetrazole rings are 2.54 (15) and 13.36 (18)° in the two cations. In the crystal, the packing of ions is stabilized by N—H⋯O and N—H⋯(O,O) hydrogen bonds, forming clusters composed of four ion pairs.

Related literature

For background to tetrazole derivatives, see: Dai & Fu (2008 ); Wang et al. (2005 ); Wen (2008 ); Xiong et al. (2002 ).

Experimental

Crystal data

C₆H₆N₅⁺·NO₃⁻
M_r = 210.17
Triclinic, $[P \overline 1]$
a = 6.9157 (14) Å
b = 10.575 (2) Å
c = 13.346 (3) Å
α = 110.10 (3)°
β = 100.65 (3)°
γ = 95.87 (3)°
V = 886.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 298 K
0.35 × 0.30 × 0.15 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.956, T_max = 0.981
9175 measured reflections
4035 independent reflections
2272 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.150
S = 1.03
4035 reflections
279 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 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
N9—H9A⋯O2ⁱ	0.93 (2)	1.80 (3)	2.700 (3)	164 (2)
N2—H2A⋯O1ⁱⁱ	0.88 (3)	2.16 (3)	2.998 (3)	161 (2)
N2—H2A⋯O2ⁱⁱ	0.88 (3)	2.16 (3)	2.890 (3)	140 (2)
N5—H5A⋯O4	0.86	1.94	2.791 (3)	168
N10—H10A⋯O4	0.86	2.06	2.891 (3)	163
N10—H10A⋯O6	0.86	2.19	2.873 (3)	137
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S160053680901839X/hb2945sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680901839X/hb2945Isup2.hkl

checkCIF report

Comment top

Tetrazole derivatives have found wide range of applications in coordination chemistry because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal-organic frameworks (Wang, et al. 2005; Xiong, et al. 2002; Wen 2008). We report here the crystal structure of the title compound, 3-(1H-tetrazol-5-yl)pyridinium 3-(2H-tetrazol-5-yl)pyridinium nitrate (Fig. 1).

The title compound contains two different isomers of the cation, one with the H atom attached to the N2 and the other with the H atom attached to N9. Each isomer is built up by two different rings. The pyridinium and the tetrazole rings are nearly coplanar and only twisted from each other by a dihedral angle of 2.54 (15)° [13.36 (18)° for the second molecule]. The geometric parameters of the tetrazole rings are comparable to those in related molecules (Wang et al. 2005; Dai & Fu, 2008).

The packing of ions is stabilized by N—H···O hydrogen bonds, to form a zero-dimentional sheets parallel to the (1 0 0) plane that is composed of four pairs of ions (Table 1, Fig. 2).

Related literature top

For background to tetrazole derivatives, see: Dai & Fu (2008); Wang et al. (2005); Wen (2008); Xiong et al. (2002).

Experimental top

Picolinonitrile (30 mmol), NaN ₃ (45 mmol), NH₄Cl (33 mmol) and DMF (50 ml) were added in a flask under nitrogen atmosphere and the mixture stirred at 383 K for 20 h. The resulting solution was then poured into ice-water (100 ml), and a white solid was obtained after adding HCl (6 M) till pH = 6. The precipitate was filtered and washed with distilled water. Colourless blocks of (I) were obtained from the crude product by slow evaporation of an ethanol/HNO₃ (50:1 v/v) solution.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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. A view of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. The crystal packing of (I) viewed along the a axis showing the two-dimensional hydrogen bonding network. H atoms not involved in hydrogen bonding (dashed lines) have been omitted for clarity.

3-(1H-Tetrazol-5-yl)pyridinium 3-(2H-tetrazol-5-yl)pyridinium dinitrate top

Crystal data top

C₆H₆N₅⁺·NO₃⁻	Z = 4
M_r = 210.17	F(000) = 432
Triclinic, P1	D_x = 1.575 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.9157 (14) Å	Cell parameters from 4035 reflections
b = 10.575 (2) Å	θ = 3.1–27.5°
c = 13.346 (3) Å	µ = 0.13 mm⁻¹
α = 110.10 (3)°	T = 298 K
β = 100.65 (3)°	Block, colourless
γ = 95.87 (3)°	0.35 × 0.30 × 0.15 mm
V = 886.2 (3) Å³

Data collection top

Rigaku Mercury2 diffractometer	4035 independent reflections
Radiation source: fine-focus sealed tube	2272 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
CCD profile fitting scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→13
T_min = 0.956, T_max = 0.981	l = −17→17
9175 measured 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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0621P)² + 0.11P] where P = (F_o² + 2F_c²)/3
4035 reflections	(Δ/σ)_max < 0.001
279 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₆H₆N₅⁺·NO₃⁻	γ = 95.87 (3)°
M_r = 210.17	V = 886.2 (3) Å³
Triclinic, P1	Z = 4
a = 6.9157 (14) Å	Mo Kα radiation
b = 10.575 (2) Å	µ = 0.13 mm⁻¹
c = 13.346 (3) Å	T = 298 K
α = 110.10 (3)°	0.35 × 0.30 × 0.15 mm
β = 100.65 (3)°

Data collection top

Rigaku Mercury2 diffractometer	4035 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	2272 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.981	R_int = 0.045
9175 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.150	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.18 e Å⁻³
4035 reflections	Δρ_min = −0.22 e Å⁻³
279 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
O4	0.6923 (3)	0.42367 (18)	0.16340 (15)	0.0676 (5)
N12	0.7836 (3)	0.3552 (2)	0.09506 (16)	0.0538 (5)
O5	0.8211 (3)	0.24401 (18)	0.09476 (15)	0.0736 (5)
N5	0.6669 (3)	0.30395 (19)	0.31822 (16)	0.0562 (5)
H5A	0.6691	0.3510	0.2770	0.067*
O6	0.8282 (3)	0.40305 (19)	0.02794 (15)	0.0719 (5)
N6	0.3306 (3)	1.0327 (2)	0.16715 (18)	0.0631 (6)
C3	0.6604 (3)	0.1553 (2)	0.44515 (18)	0.0521 (6)
H3	0.6577	0.1028	0.4885	0.063*
N1	0.2697 (3)	0.3533 (2)	0.53331 (16)	0.0581 (5)
C5	0.5298 (3)	0.3174 (2)	0.37811 (18)	0.0499 (6)
H5	0.4387	0.3755	0.3745	0.060*
C12	0.3716 (3)	0.9175 (2)	0.17583 (18)	0.0478 (5)
C6	0.3778 (3)	0.2557 (2)	0.51234 (17)	0.0466 (5)
N9	0.2512 (3)	0.8800 (2)	0.23196 (17)	0.0578 (5)
C4	0.5260 (3)	0.2439 (2)	0.44512 (17)	0.0446 (5)
C10	0.5230 (3)	0.8456 (2)	0.13170 (17)	0.0438 (5)
N2	0.1669 (3)	0.3194 (3)	0.59678 (17)	0.0641 (6)
N4	0.3414 (3)	0.1670 (2)	0.56134 (18)	0.0687 (6)
N7	0.1816 (3)	1.0644 (2)	0.2193 (2)	0.0723 (6)
C11	0.5523 (3)	0.7245 (2)	0.14313 (19)	0.0524 (6)
H11	0.4782	0.6892	0.1821	0.063*
C1	0.8009 (4)	0.2213 (3)	0.3189 (2)	0.0607 (7)
H1	0.8951	0.2166	0.2768	0.073*
N3	0.2040 (4)	0.2098 (3)	0.61492 (19)	0.0750 (7)
C2	0.7973 (4)	0.1445 (2)	0.3817 (2)	0.0577 (6)
H2	0.8872	0.0849	0.3818	0.069*
C9	0.6383 (4)	0.8947 (3)	0.0739 (2)	0.0609 (7)
H9	0.6247	0.9778	0.0664	0.073*
N10	0.6860 (3)	0.6578 (2)	0.09869 (18)	0.0673 (6)
H10A	0.7034	0.5828	0.1079	0.081*
N8	0.1327 (3)	0.9736 (2)	0.25866 (19)	0.0722 (6)
C7	0.7937 (4)	0.7011 (3)	0.0409 (2)	0.0765 (8)
H7	0.8835	0.6496	0.0096	0.092*
C8	0.7731 (4)	0.8206 (3)	0.0275 (2)	0.0752 (8)
H8	0.8490	0.8522	−0.0126	0.090*
N11	0.7936 (3)	0.4430 (2)	0.71227 (17)	0.0552 (5)
O3	0.6532 (3)	0.4772 (2)	0.75145 (17)	0.0817 (6)
O2	0.8610 (3)	0.3403 (2)	0.71981 (19)	0.0878 (6)
O1	0.8712 (3)	0.5025 (2)	0.66120 (17)	0.0809 (6)
H9A	0.236 (4)	0.802 (3)	0.248 (2)	0.069 (8)*
H2A	0.075 (4)	0.361 (3)	0.625 (2)	0.073 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O4	0.0790 (12)	0.0713 (11)	0.0790 (12)	0.0375 (10)	0.0464 (10)	0.0393 (10)
N12	0.0476 (11)	0.0620 (13)	0.0548 (12)	0.0134 (10)	0.0152 (10)	0.0229 (11)
O5	0.0974 (14)	0.0641 (12)	0.0720 (12)	0.0379 (11)	0.0306 (11)	0.0287 (10)
N5	0.0711 (14)	0.0495 (11)	0.0544 (12)	0.0048 (10)	0.0232 (11)	0.0245 (10)
O6	0.0786 (13)	0.0856 (13)	0.0746 (12)	0.0245 (10)	0.0400 (11)	0.0441 (11)
N6	0.0656 (14)	0.0485 (12)	0.0753 (15)	0.0186 (10)	0.0165 (12)	0.0207 (11)
C3	0.0610 (15)	0.0476 (13)	0.0510 (14)	0.0125 (11)	0.0136 (12)	0.0212 (11)
N1	0.0603 (13)	0.0582 (12)	0.0607 (13)	0.0165 (10)	0.0265 (11)	0.0201 (10)
C5	0.0607 (15)	0.0390 (12)	0.0513 (13)	0.0091 (10)	0.0178 (12)	0.0158 (10)
C12	0.0515 (14)	0.0453 (13)	0.0438 (12)	0.0070 (10)	0.0082 (11)	0.0150 (10)
C6	0.0520 (14)	0.0427 (12)	0.0435 (12)	0.0067 (10)	0.0136 (11)	0.0134 (10)
N9	0.0576 (13)	0.0595 (13)	0.0640 (13)	0.0192 (11)	0.0237 (11)	0.0252 (11)
C4	0.0514 (13)	0.0368 (11)	0.0438 (12)	0.0064 (10)	0.0124 (11)	0.0126 (10)
C10	0.0459 (12)	0.0440 (12)	0.0420 (12)	0.0096 (10)	0.0087 (10)	0.0168 (10)
N2	0.0613 (14)	0.0750 (16)	0.0570 (13)	0.0155 (12)	0.0265 (12)	0.0182 (12)
N4	0.0868 (16)	0.0672 (14)	0.0757 (15)	0.0224 (12)	0.0410 (13)	0.0417 (12)
N7	0.0666 (15)	0.0580 (14)	0.0874 (17)	0.0235 (11)	0.0184 (13)	0.0173 (13)
C11	0.0530 (14)	0.0531 (14)	0.0543 (14)	0.0168 (11)	0.0129 (12)	0.0217 (11)
C1	0.0588 (16)	0.0592 (15)	0.0626 (16)	0.0078 (12)	0.0244 (13)	0.0165 (13)
N3	0.0845 (17)	0.0857 (17)	0.0724 (15)	0.0164 (13)	0.0395 (14)	0.0397 (13)
C2	0.0575 (15)	0.0568 (14)	0.0624 (15)	0.0190 (12)	0.0210 (13)	0.0206 (13)
C9	0.0582 (15)	0.0695 (16)	0.0628 (16)	0.0135 (13)	0.0128 (13)	0.0342 (14)
N10	0.0663 (14)	0.0599 (13)	0.0762 (15)	0.0272 (11)	0.0133 (13)	0.0234 (12)
N8	0.0632 (14)	0.0714 (15)	0.0802 (16)	0.0264 (12)	0.0262 (12)	0.0170 (13)
C7	0.0626 (18)	0.092 (2)	0.0760 (19)	0.0310 (16)	0.0234 (16)	0.0235 (17)
C8	0.0604 (17)	0.111 (2)	0.0685 (18)	0.0207 (16)	0.0271 (15)	0.0427 (18)
N11	0.0512 (12)	0.0589 (13)	0.0604 (13)	0.0121 (10)	0.0160 (11)	0.0260 (11)
O3	0.0753 (13)	0.0926 (14)	0.1060 (15)	0.0389 (11)	0.0537 (12)	0.0489 (12)
O2	0.0878 (14)	0.0793 (13)	0.1334 (18)	0.0386 (11)	0.0536 (13)	0.0643 (13)
O1	0.0872 (14)	0.0878 (13)	0.0980 (15)	0.0216 (11)	0.0476 (12)	0.0565 (12)

Geometric parameters (Å, º) top

O4—N12	1.268 (2)	C10—C11	1.372 (3)
N12—O5	1.229 (2)	C10—C9	1.385 (3)
N12—O6	1.239 (2)	N2—N3	1.304 (3)
N5—C5	1.337 (3)	N2—H2A	0.88 (3)
N5—C1	1.338 (3)	N4—N3	1.318 (3)
N5—H5A	0.8600	N7—N8	1.288 (3)
N6—C12	1.317 (3)	C11—N10	1.324 (3)
N6—N7	1.354 (3)	C11—H11	0.9300
C3—C2	1.370 (3)	C1—C2	1.354 (3)
C3—C4	1.386 (3)	C1—H1	0.9300
C3—H3	0.9300	C2—H2	0.9300
N1—N2	1.315 (3)	C9—C8	1.377 (4)
N1—C6	1.319 (3)	C9—H9	0.9300
C5—C4	1.374 (3)	N10—C7	1.321 (3)
C5—H5	0.9300	N10—H10A	0.8600
C12—N9	1.334 (3)	C7—C8	1.354 (4)
C12—C10	1.450 (3)	C7—H7	0.9300
C6—N4	1.343 (3)	C8—H8	0.9300
C6—C4	1.469 (3)	N11—O3	1.215 (2)
N9—N8	1.345 (3)	N11—O1	1.228 (2)
N9—H9A	0.93 (2)	N11—O2	1.253 (2)

O5—N12—O6	122.0 (2)	N3—N2—H2A	118.7 (17)
O5—N12—O4	120.4 (2)	N1—N2—H2A	126.4 (17)
O6—N12—O4	117.6 (2)	N3—N4—C6	105.8 (2)
C5—N5—C1	123.6 (2)	N8—N7—N6	110.6 (2)
C5—N5—H5A	118.2	N10—C11—C10	120.0 (2)
C1—N5—H5A	118.2	N10—C11—H11	120.0
C12—N6—N7	106.2 (2)	C10—C11—H11	120.0
C2—C3—C4	120.4 (2)	N5—C1—C2	119.0 (2)
C2—C3—H3	119.8	N5—C1—H1	120.5
C4—C3—H3	119.8	C2—C1—H1	120.5
N2—N1—C6	101.2 (2)	N2—N3—N4	105.6 (2)
N5—C5—C4	118.8 (2)	C1—C2—C3	119.6 (2)
N5—C5—H5	120.6	C1—C2—H2	120.2
C4—C5—H5	120.6	C3—C2—H2	120.2
N6—C12—N9	108.2 (2)	C8—C9—C10	120.1 (2)
N6—C12—C10	125.2 (2)	C8—C9—H9	120.0
N9—C12—C10	126.7 (2)	C10—C9—H9	120.0
N1—C6—N4	112.5 (2)	C7—N10—C11	123.0 (2)
N1—C6—C4	125.0 (2)	C7—N10—H10A	118.5
N4—C6—C4	122.4 (2)	C11—N10—H10A	118.5
C12—N9—N8	108.6 (2)	N7—N8—N9	106.5 (2)
C12—N9—H9A	129.7 (16)	N10—C7—C8	119.8 (3)
N8—N9—H9A	121.5 (16)	N10—C7—H7	120.1
C5—C4—C3	118.6 (2)	C8—C7—H7	120.1
C5—C4—C6	120.5 (2)	C7—C8—C9	119.2 (3)
C3—C4—C6	120.9 (2)	C7—C8—H8	120.4
C11—C10—C9	117.9 (2)	C9—C8—H8	120.4
C11—C10—C12	120.9 (2)	O3—N11—O1	122.8 (2)
C9—C10—C12	121.2 (2)	O3—N11—O2	120.1 (2)
N3—N2—N1	114.9 (2)	O1—N11—O2	117.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N9—H9A···O2ⁱ	0.93 (2)	1.80 (3)	2.700 (3)	164 (2)
N2—H2A···O1ⁱⁱ	0.88 (3)	2.16 (3)	2.998 (3)	161 (2)
N2—H2A···O2ⁱⁱ	0.88 (3)	2.16 (3)	2.890 (3)	140 (2)
N5—H5A···O4	0.86	1.94	2.791 (3)	168
N10—H10A···O4	0.86	2.06	2.891 (3)	163
N10—H10A···O6	0.86	2.19	2.873 (3)	137

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

Experimental details

Crystal data
Chemical formula	C₆H₆N₅⁺·NO₃⁻
M_r	210.17
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	6.9157 (14), 10.575 (2), 13.346 (3)
α, β, γ (°)	110.10 (3), 100.65 (3), 95.87 (3)
V (Å³)	886.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.35 × 0.30 × 0.15

Data collection
Diffractometer	Rigaku Mercury2 diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.956, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	9175, 4035, 2272
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.150, 1.03
No. of reflections	4035
No. of parameters	279
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.22

Computer programs: CrystalClear (Rigaku, 2005), 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
N9—H9A···O2ⁱ	0.93 (2)	1.80 (3)	2.700 (3)	164 (2)
N2—H2A···O1ⁱⁱ	0.88 (3)	2.16 (3)	2.998 (3)	161 (2)
N2—H2A···O2ⁱⁱ	0.88 (3)	2.16 (3)	2.890 (3)	140 (2)
N5—H5A···O4	0.86	1.94	2.791 (3)	168
N10—H10A···O4	0.86	2.06	2.891 (3)	163
N10—H10A···O6	0.86	2.19	2.873 (3)	137

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

Acknowledgements

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

References

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