Dichloridobis[3-methyl-4-phenyl-5-(2-pyrid­yl)-4H-1,2,4-triazole-κ2N1,N5]copper(II) 3.33-hydrate

Wang, Z.; Lan, Y.; Wu, P.; Huang, L.

doi:10.1107/S1600536808007630

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 4| April 2008| Pages m593-m594

doi:10.1107/S1600536808007630

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Dichloridobis[3-methyl-4-phenyl-5-(2-pyridyl)-4H-1,2,4-triazole-κ²N¹,N⁵]copper(II) 3.33-hydrate

Zuoxiang Wang,^a ^* Yan Lan,^a Pingfeng Wu ^a and Liaocheng Huang ^a

^aOrdered Matter Science Research Center, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: wangzx0908@yahoo.com.cn

(Received 19 January 2008; accepted 20 March 2008; online 29 March 2008)

In the title compound, [CuCl₂(C₁₄H₁₂N₄)₂]·3.33H₂O, the Cu(II) atom is coordinated by two chelating 3-methyl-4-phenyl-5-(2-pyridyl)-1,2,4-triazole ligands and two chloride anions in a distorted octahedral geometry with a CuN₂N^′₂Cl₂ chromophore. The Cu atom is located on an inversion center. Two uncoordinated water molecules lie on threefold rotation axes with disordered H atoms. Two hydrogen bonds are formed between the water molecules, and another between water and a chlorido ligand.

Related literature

For related literature, see: Bencini et al. (1987 ); Koningsbruggen et al. (1995 ); Moliner et al. (1998 , 2001 ); Klingele & Brooker (2003 ); Klingele et al. (2005 ); Garcia et al. (1997 ); Lavrenova & Larionov (1998 ); Kahn & Martinez (1998 ); Koningsbruggen (2004 ); Matouzenko et al. (2004 ); Wang et al. (2005 ); Zhou et al. (2006a ,b ).

Experimental

Crystal data

[CuCl₂(C₁₄H₁₂N₄)₂]·3.33H₂O
M_r = 667.04
Rhombohedral, $[R \overline 3]$
a = 21.5496 (13) Å
c = 17.619 (2) Å
V = 7086.0 (10) Å³
Z = 9
Mo Kα radiation
μ = 0.91 mm⁻¹
T = 293 (2) K
0.28 × 0.26 × 0.22 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.78, T_max = 0.82
12784 measured reflections
3091 independent reflections
2155 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.114
S = 1.06
3091 reflections
194 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.82 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Cu1—N4	2.006 (2)
Cu1—N7	2.023 (2)
Cu1—Cl1	2.7537 (9)

N4ⁱ—Cu1—N7	99.70 (9)
N4—Cu1—N7	80.30 (9)
N4ⁱ—Cu1—Cl1	96.83 (8)
N4—Cu1—Cl1	83.17 (8)
N7—Cu1—Cl1	89.45 (7)
N7—Cu1—Cl1ⁱ	90.55 (7)
Symmetry code: (i) -x+1, -y+2, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯Cl1	0.85	2.20	3.053 (2)	179
O1—H1A⋯O2	0.85	2.43	2.932 (3)	119
O2—H2B⋯O2ⁱⁱ	0.85	1.88	2.505 (8)	130
Symmetry code: (ii) $[-x+{\script{2\over 3}}, -y+{\script{4\over 3}}, -z+{\script{4\over 3}}]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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 I, New_Global_Publ_Block. DOI: 10.1107/S1600536808007630/cf2182sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808007630/cf2182Isup2.hkl

checkCIF report

Comment top

The coordination chemistry of 1,2,4-triazole derivatives has attracted great attention in recent years (Bencini et al., 1987; Koningsbruggen et al., 1995; Moliner et al., 1998, 2001; Klingele & Brooker, 2003; Klingele et al., 2005). Some spin-crossover complexes of 1,2,4-triazoles with iron(II) salts have been reported, which could be used as molecular-based memory devices, displays and optical switches (Garcia et al., 1997; Lavrenova & Larionov, 1998; Kahn & Martinez, 1998; Koningsbruggen, 2004; Matouzenko et al., 2004). We have synthesized some new 3,4-disubstituted-5-(2-pyridyl)-1,2,4-triazoles and their transition-metal complexes (Wang et al., 2005; Zhou et al., 2006a,b). We report here the crystal structure analysis of the title compound, (I).

The structure of (I) is shown in Fig.1. In the crystal structure, the Cu(II) atom is coordinated by two chelating 3-methyl-4-phenyl-5-(2-pyridyl)-1,2,4-triazole ligands and two chloride anions in a distorted octahedral geometry with a CuN₂N^'₂Cl₂ chromophore. Two hydrogen bonds are formed between the water molecules, and another involves the chloro ligand.

Related literature top

For related literature, see: Bencini et al. (1987); Koningsbruggen et al. (1995); Moliner et al. (1998, 2001); Klingele & Brooker (2003); Klingele et al. (2005); Garcia et al. (1997); Lavrenova & Larionov (1998); Kahn & Martinez (1998); Koningsbruggen (2004); Matouzenko et al. (2004); Wang et al. (2005); Zhou et al. (2006a,b).

Experimental top

To a warm solution of 0.944 g 3-methyl-4-phenyl-5-(2-pyridyl)-1,2,4-triazole (4.0 mmol) in 20 ml e thanol, 0.270 g copper(II) chloride (2.0 mmol) was added. The filtrate was left to stand at room temperature for several days, and blue single crystals suitable for X-ray diffraction were collected.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 the title compound with the atomic labelling. Displacement ellipsoids are shown at the 30% probability level. [Symmetry code i: -x + 1, -y + 2, -z + 2.]

Dichloridobis[3-methyl-4-phenyl-5-(2-pyridyl)-4H-1,2,4-triazole- κ²N¹,N⁵]copper(II) 3.33-hydrate top

Crystal data top

[CuCl₂(C₁₄H₁₂N₄)₂]·3.33H₂O	F(000) = 3099
M_r = 667.04	D_x = 1.407 Mg m⁻³
Rhombohedral, R3	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3	Cell parameters from 3501 reflections
a = 21.5496 (13) Å	θ = 2.5–23.9°
c = 17.619 (2) Å	µ = 0.91 mm⁻¹
α = 90°	T = 293 K
γ = 120°	Polyhedron, blue
V = 7086.0 (10) Å³	0.28 × 0.26 × 0.22 mm
Z = 9

Data collection top

Bruker SMART APEX CCD diffractometer	3091 independent reflections
Radiation source: sealed tube	2155 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.055
ϕ and ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −26→26
T_min = 0.78, T_max = 0.82	k = −21→26
12784 measured reflections	l = −21→19

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) = 0.114	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.05P)²] where P = (F_o² + 2F_c²)/3
3091 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.82 e Å⁻³

Crystal data top

[CuCl₂(C₁₄H₁₂N₄)₂]·3.33H₂O	V = 7086.0 (10) Å³
M_r = 667.04	Z = 9
Rhombohedral, R3	Mo Kα radiation
a = 21.5496 (13) Å	µ = 0.91 mm⁻¹
c = 17.619 (2) Å	T = 293 K
α = 90°	0.28 × 0.26 × 0.22 mm
γ = 120°

Data collection top

Bruker SMART APEX CCD diffractometer	3091 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2155 reflections with I > 2σ(I)
T_min = 0.78, T_max = 0.82	R_int = 0.055
12784 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.06	Δρ_max = 0.31 e Å⁻³
3091 reflections	Δρ_min = −0.82 e Å⁻³
194 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	Occ. (<1)
Cu1	0.5000	1.0000	1.0000	0.04781 (19)
C1	0.56211 (17)	0.87212 (17)	0.88733 (16)	0.0408 (7)
C2	0.54547 (13)	0.96307 (14)	0.86885 (15)	0.0280 (6)
C3	0.53495 (14)	1.02034 (15)	0.84128 (15)	0.0292 (6)
C4	0.54676 (16)	1.04762 (16)	0.76855 (16)	0.0366 (7)
H4	0.5626	1.0287	0.7307	0.044*
C5	0.53496 (19)	1.10252 (19)	0.75306 (16)	0.0459 (8)
H5	0.5416	1.1206	0.7040	0.055*
C6	0.51311 (18)	1.13172 (19)	0.80953 (16)	0.0444 (8)
H6	0.5053	1.1696	0.7995	0.053*
C7	0.50315 (17)	1.10251 (16)	0.88239 (17)	0.0412 (7)
H7	0.4894	1.1222	0.9214	0.049*
C8	0.57362 (19)	0.81162 (17)	0.87105 (17)	0.0445 (8)
H8A	0.6136	0.8167	0.9001	0.067*
H8B	0.5834	0.8112	0.8179	0.067*
H8C	0.5314	0.7675	0.8845	0.067*
C9	0.56300 (18)	0.90787 (16)	0.74991 (16)	0.0380 (7)
C10	0.4997 (2)	0.86341 (18)	0.71288 (19)	0.0504 (8)
H10	0.4565	0.8395	0.7389	0.061*
C11	0.5032 (2)	0.8556 (2)	0.6345 (2)	0.0574 (9)
H11	0.4617	0.8262	0.6072	0.069*
C12	0.56770 (19)	0.89132 (18)	0.59789 (17)	0.0458 (8)
H12	0.5696	0.8859	0.5457	0.055*
C13	0.6281 (2)	0.9340 (2)	0.6358 (2)	0.0563 (9)
H13	0.6711	0.9579	0.6093	0.068*
C14	0.62835 (19)	0.94346 (18)	0.71455 (19)	0.0509 (8)
H14	0.6704	0.9722	0.7413	0.061*
N4	0.54193 (13)	0.94977 (13)	0.94163 (13)	0.0361 (6)
N5	0.55287 (15)	0.89213 (14)	0.95473 (14)	0.0411 (6)
N6	0.55975 (13)	0.91589 (13)	0.83203 (13)	0.0333 (5)
N7	0.51276 (12)	1.04744 (13)	0.89762 (13)	0.0356 (6)
Cl1	0.37209 (5)	0.88666 (5)	0.95079 (5)	0.0581 (3)
O1	0.38596 (12)	0.77383 (11)	0.85941 (11)	0.0424 (5)
H1D	0.3825	0.8054	0.8850	0.051*
H1A	0.3444	0.7409	0.8465	0.051*
O2	0.3333	0.6667	0.7377 (2)	0.0567 (11)
H2A	0.2895	0.6359	0.7304	0.068*	0.334
H2B	0.3504	0.6925	0.6983	0.068*	0.334
O3	0.6667	0.3333	0.70495 (19)	0.0428 (9)
H3A	0.6650	0.3103	0.6651	0.051*	0.3333
H3C	0.6474	0.3042	0.7416	0.051*	0.3333

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0484 (3)	0.0501 (4)	0.0456 (4)	0.0251 (3)	0.0044 (3)	0.0055 (3)
C1	0.0531 (19)	0.0518 (18)	0.0298 (17)	0.0356 (16)	0.0098 (14)	0.0032 (14)
C2	0.0275 (14)	0.0340 (15)	0.0229 (13)	0.0158 (12)	0.0030 (11)	−0.0039 (11)
C3	0.0295 (14)	0.0369 (15)	0.0227 (13)	0.0178 (12)	0.0003 (11)	−0.0025 (11)
C4	0.0469 (17)	0.0542 (18)	0.0184 (13)	0.0326 (15)	−0.0003 (12)	−0.0004 (13)
C5	0.062 (2)	0.068 (2)	0.0205 (14)	0.0417 (19)	0.0051 (14)	0.0132 (15)
C6	0.064 (2)	0.062 (2)	0.0292 (15)	0.0477 (18)	0.0059 (15)	0.0107 (15)
C7	0.060 (2)	0.0531 (19)	0.0302 (15)	0.0429 (16)	0.0118 (14)	0.0119 (14)
C8	0.065 (2)	0.052 (2)	0.0315 (17)	0.0406 (18)	0.0071 (15)	0.0038 (14)
C9	0.064 (2)	0.0440 (17)	0.0176 (14)	0.0356 (16)	0.0047 (14)	−0.0010 (12)
C10	0.064 (2)	0.053 (2)	0.0408 (18)	0.0341 (18)	0.0118 (17)	0.0035 (16)
C11	0.062 (2)	0.070 (2)	0.0377 (19)	0.031 (2)	−0.0055 (18)	−0.0072 (18)
C12	0.070 (2)	0.057 (2)	0.0244 (16)	0.0420 (19)	0.0051 (16)	−0.0025 (14)
C13	0.063 (2)	0.068 (2)	0.042 (2)	0.036 (2)	−0.0001 (18)	0.0004 (18)
C14	0.050 (2)	0.055 (2)	0.0416 (19)	0.0214 (17)	−0.0045 (16)	−0.0022 (16)
N4	0.0456 (14)	0.0424 (14)	0.0237 (13)	0.0245 (12)	0.0007 (10)	0.0104 (10)
N5	0.0589 (17)	0.0484 (15)	0.0291 (13)	0.0367 (14)	0.0058 (12)	0.0062 (11)
N6	0.0484 (15)	0.0400 (13)	0.0197 (11)	0.0282 (12)	0.0069 (10)	−0.0004 (10)
N7	0.0401 (13)	0.0454 (14)	0.0329 (13)	0.0303 (12)	−0.0029 (11)	−0.0059 (11)
Cl1	0.0439 (5)	0.0671 (6)	0.0520 (5)	0.0191 (4)	0.0020 (4)	0.0033 (4)
O1	0.0534 (13)	0.0488 (13)	0.0327 (11)	0.0313 (11)	0.0046 (10)	0.0029 (10)
O2	0.0633 (16)	0.0633 (16)	0.043 (3)	0.0317 (8)	0.000	0.000
O3	0.0519 (14)	0.0519 (14)	0.0245 (18)	0.0259 (7)	0.000	0.000

Geometric parameters (Å, º) top

Cu1—N4ⁱ	2.006 (2)	C8—H8A	0.960
Cu1—N4	2.006 (2)	C8—H8B	0.960
Cu1—N7	2.023 (2)	C8—H8C	0.960
Cu1—N7ⁱ	2.023 (2)	C9—C14	1.371 (5)
Cu1—Cl1	2.7537 (9)	C9—C10	1.377 (5)
Cu1—Cl1ⁱ	2.7537 (9)	C9—N6	1.463 (3)
C1—N5	1.312 (4)	C10—C11	1.398 (5)
C1—N6	1.375 (4)	C10—H10	0.930
C1—C8	1.472 (4)	C11—C12	1.368 (5)
C2—N4	1.308 (3)	C11—H11	0.930
C2—N6	1.365 (3)	C12—C13	1.338 (5)
C2—C3	1.446 (4)	C12—H12	0.930
C3—N7	1.354 (3)	C13—C14	1.402 (5)
C3—C4	1.380 (4)	C13—H13	0.930
C4—C5	1.356 (4)	C14—H14	0.930
C4—H4	0.930	N4—N5	1.395 (3)
C5—C6	1.380 (4)	O1—H1D	0.850
C5—H5	0.930	O1—H1A	0.850
C6—C7	1.398 (4)	O2—H2A	0.850
C6—H6	0.930	O2—H2B	0.8499
C7—N7	1.330 (4)	O3—H3A	0.850
C7—H7	0.930	O3—H3C	0.850

N4ⁱ—Cu1—N4	180.000 (1)	C1—C8—H8B	109.5
N4ⁱ—Cu1—N7	99.70 (9)	H8A—C8—H8B	109.5
N4—Cu1—N7	80.30 (9)	C1—C8—H8C	109.5
N4ⁱ—Cu1—N7ⁱ	80.30 (9)	H8A—C8—H8C	109.5
N4—Cu1—N7ⁱ	99.70 (9)	H8B—C8—H8C	109.5
N7—Cu1—N7ⁱ	180.000 (1)	C14—C9—C10	123.8 (3)
N4ⁱ—Cu1—Cl1	96.83 (8)	C14—C9—N6	118.7 (3)
N4—Cu1—Cl1	83.17 (8)	C10—C9—N6	117.5 (3)
N7—Cu1—Cl1	89.45 (7)	C9—C10—C11	117.3 (3)
N4ⁱ—Cu1—Cl1ⁱ	83.17 (8)	C9—C10—H10	121.4
N4—Cu1—Cl1ⁱ	96.83 (8)	C11—C10—H10	121.4
N7—Cu1—Cl1ⁱ	90.55 (7)	C12—C11—C10	119.9 (3)
N7ⁱ—Cu1—Cl1ⁱ	89.45 (7)	C12—C11—H11	120.1
Cl1—Cu1—Cl1ⁱ	180.00 (4)	C10—C11—H11	120.1
N5—C1—N6	110.6 (3)	C13—C12—C11	121.2 (3)
N5—C1—C8	126.0 (3)	C13—C12—H12	119.4
N6—C1—C8	123.4 (3)	C11—C12—H12	119.4
N4—C2—N6	108.2 (2)	C12—C13—C14	121.7 (3)
N4—C2—C3	120.0 (2)	C12—C13—H13	119.2
N6—C2—C3	131.8 (2)	C14—C13—H13	119.2
N7—C3—C4	121.8 (3)	C9—C14—C13	116.1 (3)
N7—C3—C2	111.2 (2)	C9—C14—H14	121.9
C4—C3—C2	127.0 (2)	C13—C14—H14	121.9
C5—C4—C3	118.9 (3)	C2—N4—N5	109.9 (2)
C5—C4—H4	120.5	C2—N4—Cu1	112.15 (18)
C3—C4—H4	120.5	N5—N4—Cu1	135.90 (18)
C4—C5—C6	120.6 (3)	C1—N5—N4	105.3 (2)
C4—C5—H5	119.7	C2—N6—C1	105.9 (2)
C6—C5—H5	119.7	C2—N6—C9	126.9 (2)
C5—C6—C7	117.9 (3)	C1—N6—C9	126.8 (2)
C5—C6—H6	121.1	C7—N7—C3	118.9 (3)
C7—C6—H6	121.1	C7—N7—Cu1	126.0 (2)
N7—C7—C6	122.0 (3)	C3—N7—Cu1	115.07 (19)
N7—C7—H7	119.0	H1D—O1—H1A	109.5
C6—C7—H7	119.0	H2A—O2—H2B	109.5
C1—C8—H8A	109.5	H3A—O3—H3C	109.5

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Cl1	0.85	2.20	3.053 (2)	179
O1—H1A···O2	0.85	2.43	2.932 (3)	119
O2—H2B···O2ⁱⁱ	0.85	1.88	2.505 (8)	130

Symmetry code: (ii) −x+2/3, −y+4/3, −z+4/3.

Experimental details

Crystal data
Chemical formula	[CuCl₂(C₁₄H₁₂N₄)₂]·3.33H₂O
M_r	667.04
Crystal system, space group	Rhombohedral, R3
Temperature (K)	293
a, c (Å)	21.5496 (13), 17.619 (2)
V (Å³)	7086.0 (10)
Z	9
Radiation type	Mo Kα
µ (mm⁻¹)	0.91
Crystal size (mm)	0.28 × 0.26 × 0.22

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.78, 0.82
No. of measured, independent and observed [I > 2σ(I)] reflections	12784, 3091, 2155
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.114, 1.06
No. of reflections	3091
No. of parameters	194
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.82

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Cu1—N4	2.006 (2)	Cu1—Cl1	2.7537 (9)
Cu1—N7	2.023 (2)

N4ⁱ—Cu1—N7	99.70 (9)	N4—Cu1—Cl1	83.17 (8)
N4—Cu1—N7	80.30 (9)	N7—Cu1—Cl1	89.45 (7)
N4ⁱ—Cu1—Cl1	96.83 (8)	N7—Cu1—Cl1ⁱ	90.55 (7)

Symmetry code: (i) −x+1, −y+2, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Cl1	0.85	2.20	3.053 (2)	179.3
O1—H1A···O2	0.85	2.43	2.932 (3)	118.5
O2—H2B···O2ⁱⁱ	0.85	1.88	2.505 (8)	129.6

Symmetry code: (ii) −x+2/3, −y+4/3, −z+4/3.

Acknowledgements

We are grateful to Jingye Pharmochemical Pilot Plant for financial assistance though project 8507041056.

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