(2-Chloro­phen­yl)(diphenyl­phosphor­yl)methanol

Liu, W.-Y.; Huo, P.

doi:10.1107/S1600536807057674

organic compounds

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Volume 64| Part 1| January 2008| Page o233

https://doi.org/10.1107/S1600536807057674

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(2-Chlorophenyl)(diphenylphosphoryl)methanol

Wan-Yun Liu ^a ^* and Ping Huo ^a

^aDepartment of Chemistry and Bioengineering, Yichun University, Yichun 336000, People's Republic of China
^*Correspondence e-mail: liuwanyun2006@tom.com

(Received 18 October 2007; accepted 10 November 2007; online 12 December 2007)

The title compound, C₁₉H₁₆ClO₂P, was obtained by the reaction of diphenylphosphine oxide with 2-chlorobenzaldehyde. The molecule has a tetrahedral structure at the P atom. The dihedral angle between the phenyl rings attached to the P atom is 80.4 (1)°. The molecules are linked together by intermolecular O—H⋯O and C—H⋯O hydrogen-bonding interactrions. The crystal studied was an inversion twin.

Related literature

For general background, see: Clark et al. (2002 ). For related structures, see: Dankowski et al. (1979 ); Liu et al. (2007 ).

Experimental

Crystal data

C₁₉H₁₆ClO₂P
M_r = 342.74
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.0943 (4) Å
b = 10.9172 (6) Å
c = 18.0657 (12) Å
V = 1793.64 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 (2) K
0.57 × 0.20 × 0.10 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; (Bruker, 2001 ) T_min = 0.844, T_max = 0.970
8361 measured reflections
3466 independent reflections
2494 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.084
S = 0.91
3466 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ), 1437 Friedel pairs
Flack parameter: 0.55 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1ⁱ	0.82	1.82	2.602 (2)	158
C1—H3A⋯O1ⁱ	0.98	2.56	3.059 (2)	111
C16—H33A⋯O2ⁱⁱ	0.93	2.56	3.318 (3)	139
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807057674/xu2343sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807057674/xu2343Isup2.hkl

checkCIF report

Comment top

The title compound is an analog of (diphenylphosphinoyl)phenylmethanol, which was employed as a ligand in the rhodiumcatalyzed hydroformylation of alkenes, with good conversions and regioselectivities (Clark et al., 2002).

The molecular structure is shown in Fig. 1. Bond lengths and angles are in agreement with those reported for similar compounds (Dankowski et al., 1979; Liu et al., 2007). The dihedral angle between the C8-phenyl and C14-phenyl planes is 80.4 (1)°. The O—H···O and C—H···O hydrogen bonds (Table 1) involving the hydroxyl group link the molecules into a supra-molecular structure.

Related literature top

For general background, see: Clark et al. (2002). For related structures, see: Dankowski et al. (1979); Liu et al. (2007).

Experimental top

To a solution of 2-chlorobenzaldehyde (0.28 g, 2.0 mmol) and diphenylphosphine oxide (0.41 g, 2.0 mmol) in tetrahydrofuran (10 ml) at 273 K was added dropwise triethylamine (0.30 ml, 2.0 mmol). The cooling bath was removed and the mixture warmed to ambient temperature for 2 h. The solvent was concentrated under vacuum and the crude product was purified by column chromatography (petroleum ether-ethyl acetate, 1:1) to give the title compound as a white solid in 85% yield. Single crystals were obtained by slow evaporation of a methanol solution.

Structure description top

For general background, see: Clark et al. (2002). For related structures, see: Dankowski et al. (1979); Liu et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of (I), showing 50% probability displacement ellipsoids (arbitrary spheres for H atoms).

'(2-Chlorophenyl)(diphenylphosphoryl)methanol' top

Crystal data top

C₁₉H₁₆ClO₂P	F(000) = 712
M_r = 342.74	D_x = 1.269 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3220 reflections
a = 9.0943 (4) Å	θ = 2.5–32.6°
b = 10.9172 (6) Å	µ = 0.31 mm⁻¹
c = 18.0657 (12) Å	T = 293 K
V = 1793.64 (17) Å³	Plate, colorless
Z = 4	0.57 × 0.20 × 0.10 mm

Data collection top

Bruker APEX area-detector diffractometer	3466 independent reflections
Radiation source: fine-focus sealed tube	2494 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 26.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; (Bruker, 2001)	h = −11→10
T_min = 0.844, T_max = 0.970	k = −13→13
8361 measured reflections	l = −22→19

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)] = 0.035	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0482P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max < 0.001
3466 reflections	Δρ_max = 0.20 e Å⁻³
208 parameters	Δρ_min = −0.26 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1437 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.55 (8)

Crystal data top

C₁₉H₁₆ClO₂P	V = 1793.64 (17) Å³
M_r = 342.74	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.0943 (4) Å	µ = 0.31 mm⁻¹
b = 10.9172 (6) Å	T = 293 K
c = 18.0657 (12) Å	0.57 × 0.20 × 0.10 mm

Data collection top

Bruker APEX area-detector diffractometer	3466 independent reflections
Absorption correction: multi-scan (SADABS; (Bruker, 2001)	2494 reflections with I > 2σ(I)
T_min = 0.844, T_max = 0.970	R_int = 0.035
8361 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	H-atom parameters constrained
wR(F²) = 0.084	Δρ_max = 0.20 e Å⁻³
S = 0.91	Δρ_min = −0.26 e Å⁻³
3466 reflections	Absolute structure: Flack (1983), 1437 Friedel pairs
208 parameters	Absolute structure parameter: 0.55 (8)
0 restraints

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
P1	0.39075 (6)	0.07346 (5)	0.22300 (3)	0.03563 (15)
Cl1	0.68961 (8)	0.08726 (10)	0.36635 (5)	0.0874 (3)
C1	0.4310 (2)	0.20391 (18)	0.28358 (14)	0.0371 (5)
H3A	0.5340	0.2276	0.2764	0.045*
C2	0.4092 (3)	0.1697 (2)	0.36374 (14)	0.0425 (6)
C3	0.5177 (3)	0.1153 (3)	0.40525 (16)	0.0574 (7)
C4	0.4977 (4)	0.0838 (3)	0.47859 (18)	0.0795 (9)
H26A	0.5729	0.0468	0.5054	0.095*
C5	0.3652 (5)	0.1080 (3)	0.5109 (2)	0.0929 (12)
H12A	0.3501	0.0876	0.5603	0.112*
C6	0.2538 (4)	0.1621 (3)	0.4712 (2)	0.0850 (11)
H27A	0.1637	0.1775	0.4937	0.102*
C7	0.2752 (3)	0.1935 (2)	0.39825 (17)	0.0616 (8)
H10A	0.1998	0.2308	0.3718	0.074*
C8	0.4778 (2)	0.1058 (2)	0.13569 (14)	0.0405 (6)
C9	0.5076 (3)	0.0066 (3)	0.09105 (16)	0.0575 (7)
H8A	0.4765	−0.0711	0.1053	0.069*
C10	0.5824 (4)	0.0211 (3)	0.02620 (17)	0.0771 (10)
H19A	0.6024	−0.0467	−0.0033	0.093*
C11	0.6281 (4)	0.1348 (3)	0.00437 (18)	0.0807 (10)
H21A	0.6781	0.1442	−0.0402	0.097*
C12	0.6006 (4)	0.2345 (3)	0.04770 (18)	0.0818 (10)
H20A	0.6325	0.3117	0.0331	0.098*
C13	0.5251 (3)	0.2202 (3)	0.11336 (17)	0.0641 (8)
H11A	0.5058	0.2881	0.1428	0.077*
C14	0.1961 (2)	0.0688 (2)	0.20812 (13)	0.0421 (5)
C15	0.1179 (3)	−0.0269 (3)	0.23868 (18)	0.0702 (8)
H13A	0.1659	−0.0852	0.2674	0.084*
C16	−0.0321 (4)	−0.0361 (4)	0.2266 (3)	0.0999 (12)
H33A	−0.0845	−0.1009	0.2471	0.120*
C17	−0.1028 (4)	0.0485 (4)	0.1851 (2)	0.0939 (11)
H22A	−0.2038	0.0421	0.1780	0.113*
C18	−0.0284 (3)	0.1419 (3)	0.1541 (2)	0.0795 (10)
H17A	−0.0780	0.1992	0.1253	0.095*
C19	0.1227 (3)	0.1530 (2)	0.16514 (16)	0.0590 (7)
H14A	0.1740	0.2173	0.1434	0.071*
O1	0.44309 (17)	−0.04402 (12)	0.25449 (9)	0.0471 (4)
O2	0.34008 (16)	0.30243 (12)	0.26047 (10)	0.0491 (5)
H2A	0.3910	0.3630	0.2525	0.074*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0332 (3)	0.0318 (3)	0.0419 (3)	0.0014 (3)	0.0010 (3)	0.0005 (3)
Cl1	0.0540 (4)	0.1355 (7)	0.0726 (5)	0.0196 (5)	−0.0150 (4)	0.0185 (6)
C1	0.0298 (11)	0.0323 (11)	0.0493 (14)	0.0003 (9)	0.0007 (11)	−0.0017 (11)
C2	0.0517 (14)	0.0346 (12)	0.0413 (14)	−0.0059 (11)	0.0048 (14)	−0.0053 (11)
C3	0.0652 (17)	0.0603 (18)	0.0467 (16)	−0.0005 (14)	−0.0054 (15)	−0.0049 (14)
C4	0.099 (2)	0.089 (2)	0.0506 (19)	−0.005 (2)	−0.0087 (18)	0.0145 (18)
C5	0.140 (4)	0.091 (3)	0.0477 (18)	−0.015 (3)	0.024 (2)	0.0091 (18)
C6	0.103 (3)	0.078 (2)	0.074 (2)	0.005 (2)	0.041 (2)	0.0077 (19)
C7	0.0624 (17)	0.0542 (16)	0.068 (2)	0.0005 (14)	0.0213 (16)	0.0022 (15)
C8	0.0352 (11)	0.0436 (14)	0.0427 (14)	0.0033 (10)	0.0008 (11)	−0.0010 (12)
C9	0.0623 (18)	0.0587 (17)	0.0515 (17)	0.0010 (14)	0.0121 (15)	−0.0047 (14)
C10	0.092 (3)	0.081 (2)	0.059 (2)	0.0148 (19)	0.0227 (19)	−0.0111 (17)
C11	0.095 (2)	0.091 (3)	0.056 (2)	0.014 (2)	0.032 (2)	0.0139 (18)
C12	0.106 (3)	0.0631 (19)	0.076 (2)	−0.003 (2)	0.032 (2)	0.0198 (17)
C13	0.080 (2)	0.0497 (17)	0.062 (2)	0.0061 (15)	0.0202 (17)	0.0086 (14)
C14	0.0349 (11)	0.0469 (12)	0.0446 (14)	−0.0067 (12)	0.0003 (10)	−0.0040 (13)
C15	0.0531 (16)	0.0746 (17)	0.083 (2)	−0.0208 (15)	−0.0027 (17)	0.0197 (16)
C16	0.060 (2)	0.122 (3)	0.117 (3)	−0.044 (2)	−0.001 (2)	0.021 (3)
C17	0.0360 (14)	0.143 (3)	0.103 (3)	−0.021 (2)	−0.0043 (19)	−0.006 (3)
C18	0.0530 (18)	0.099 (2)	0.086 (3)	0.0122 (18)	−0.0214 (18)	0.001 (2)
C19	0.0388 (14)	0.0696 (17)	0.069 (2)	−0.0036 (14)	−0.0068 (14)	0.0108 (14)
O1	0.0562 (10)	0.0317 (8)	0.0535 (10)	0.0105 (7)	0.0034 (9)	0.0033 (7)
O2	0.0413 (8)	0.0317 (8)	0.0743 (13)	0.0030 (6)	−0.0005 (9)	0.0047 (8)

Geometric parameters (Å, º) top

P1—O1	1.4816 (15)	C9—H8A	0.9300
P1—C14	1.792 (2)	C10—C11	1.367 (4)
P1—C8	1.800 (3)	C10—H19A	0.9300
P1—C1	1.833 (2)	C11—C12	1.364 (4)
Cl1—C3	1.741 (3)	C11—H21A	0.9300
C1—O2	1.420 (2)	C12—C13	1.380 (4)
C1—C2	1.509 (3)	C12—H20A	0.9300
C1—H3A	0.9800	C13—H11A	0.9300
C2—C3	1.374 (4)	C14—C19	1.375 (3)
C2—C7	1.393 (3)	C14—C15	1.379 (3)
C3—C4	1.381 (4)	C15—C16	1.385 (4)
C4—C5	1.364 (5)	C15—H13A	0.9300
C4—H26A	0.9300	C16—C17	1.351 (5)
C5—C6	1.374 (5)	C16—H33A	0.9300
C5—H12A	0.9300	C17—C18	1.346 (5)
C6—C7	1.375 (4)	C17—H22A	0.9300
C6—H27A	0.9300	C18—C19	1.394 (4)
C7—H10A	0.9300	C18—H17A	0.9300
C8—C9	1.378 (3)	C19—H14A	0.9300
C8—C13	1.380 (3)	O2—H2A	0.8200
C9—C10	1.364 (4)

O1—P1—C14	110.54 (11)	C10—C9—H8A	119.7
O1—P1—C8	111.42 (10)	C8—C9—H8A	119.7
C14—P1—C8	107.99 (11)	C9—C10—C11	120.3 (3)
O1—P1—C1	112.28 (10)	C9—C10—H19A	119.8
C14—P1—C1	107.99 (10)	C11—C10—H19A	119.8
C8—P1—C1	106.42 (11)	C12—C11—C10	120.2 (3)
O2—C1—C2	113.15 (18)	C12—C11—H21A	119.9
O2—C1—P1	107.26 (15)	C10—C11—H21A	119.9
C2—C1—P1	110.76 (15)	C11—C12—C13	119.6 (3)
O2—C1—H3A	108.5	C11—C12—H20A	120.2
C2—C1—H3A	108.5	C13—C12—H20A	120.2
P1—C1—H3A	108.5	C12—C13—C8	120.6 (3)
C3—C2—C7	117.7 (2)	C12—C13—H11A	119.7
C3—C2—C1	122.4 (2)	C8—C13—H11A	119.7
C7—C2—C1	119.9 (2)	C19—C14—C15	118.8 (2)
C2—C3—C4	122.4 (3)	C19—C14—P1	123.04 (18)
C2—C3—Cl1	120.0 (2)	C15—C14—P1	118.1 (2)
C4—C3—Cl1	117.5 (3)	C14—C15—C16	120.0 (3)
C5—C4—C3	118.6 (3)	C14—C15—H13A	120.0
C5—C4—H26A	120.7	C16—C15—H13A	120.0
C3—C4—H26A	120.7	C17—C16—C15	120.4 (3)
C4—C5—C6	120.7 (3)	C17—C16—H33A	119.8
C4—C5—H12A	119.6	C15—C16—H33A	119.8
C6—C5—H12A	119.6	C18—C17—C16	120.6 (3)
C5—C6—C7	120.2 (3)	C18—C17—H22A	119.7
C5—C6—H27A	119.9	C16—C17—H22A	119.7
C7—C6—H27A	119.9	C17—C18—C19	120.1 (3)
C6—C7—C2	120.4 (3)	C17—C18—H17A	120.0
C6—C7—H10A	119.8	C19—C18—H17A	120.0
C2—C7—H10A	119.8	C14—C19—C18	120.1 (3)
C9—C8—C13	118.6 (3)	C14—C19—H14A	120.0
C9—C8—P1	116.43 (19)	C18—C19—H14A	120.0
C13—C8—P1	124.8 (2)	C1—O2—H2A	109.5
C10—C9—C8	120.6 (3)

O1—P1—C1—O2	−162.66 (13)	C14—P1—C8—C13	98.3 (2)
C14—P1—C1—O2	−40.54 (17)	C1—P1—C8—C13	−17.4 (3)
C8—P1—C1—O2	75.19 (16)	C13—C8—C9—C10	0.1 (4)
O1—P1—C1—C2	−38.74 (18)	P1—C8—C9—C10	−175.5 (3)
C14—P1—C1—C2	83.38 (18)	C8—C9—C10—C11	−0.4 (5)
C8—P1—C1—C2	−160.89 (15)	C9—C10—C11—C12	0.7 (6)
O2—C1—C2—C3	−153.6 (2)	C10—C11—C12—C13	−0.6 (6)
P1—C1—C2—C3	85.9 (2)	C11—C12—C13—C8	0.3 (5)
O2—C1—C2—C7	26.2 (3)	C9—C8—C13—C12	0.0 (4)
P1—C1—C2—C7	−94.3 (2)	P1—C8—C13—C12	175.1 (3)
C7—C2—C3—C4	0.3 (4)	O1—P1—C14—C19	−165.4 (2)
C1—C2—C3—C4	−179.9 (3)	C8—P1—C14—C19	−43.2 (2)
C7—C2—C3—Cl1	−178.04 (19)	C1—P1—C14—C19	71.5 (2)
C1—C2—C3—Cl1	1.8 (3)	O1—P1—C14—C15	11.7 (2)
C2—C3—C4—C5	−0.2 (5)	C8—P1—C14—C15	133.8 (2)
Cl1—C3—C4—C5	178.2 (3)	C1—P1—C14—C15	−111.5 (2)
C3—C4—C5—C6	0.3 (5)	C19—C14—C15—C16	−0.8 (5)
C4—C5—C6—C7	−0.5 (5)	P1—C14—C15—C16	−178.0 (3)
C5—C6—C7—C2	0.7 (5)	C14—C15—C16—C17	−0.2 (6)
C3—C2—C7—C6	−0.6 (4)	C15—C16—C17—C18	1.0 (6)
C1—C2—C7—C6	179.6 (3)	C16—C17—C18—C19	−0.7 (6)
O1—P1—C8—C9	35.1 (2)	C15—C14—C19—C18	1.1 (4)
C14—P1—C8—C9	−86.4 (2)	P1—C14—C19—C18	178.1 (2)
C1—P1—C8—C9	157.82 (19)	C17—C18—C19—C14	−0.4 (5)
O1—P1—C8—C13	−140.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.82	1.82	2.602 (2)	158
C1—H3A···O1ⁱ	0.98	2.56	3.059 (2)	111
C16—H33A···O2ⁱⁱ	0.93	2.56	3.318 (3)	139

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

Experimental details

Crystal data
Chemical formula	C₁₉H₁₆ClO₂P
M_r	342.74
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	9.0943 (4), 10.9172 (6), 18.0657 (12)
V (Å³)	1793.64 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.57 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; (Bruker, 2001)
T_min, T_max	0.844, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	8361, 3466, 2494
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.084, 0.91
No. of reflections	3466
No. of parameters	208
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.26
Absolute structure	Flack (1983), 1437 Friedel pairs
Absolute structure parameter	0.55 (8)

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.82	1.82	2.602 (2)	158.3
C1—H3A···O1ⁱ	0.98	2.56	3.059 (2)	111.3
C16—H33A···O2ⁱⁱ	0.93	2.56	3.318 (3)	139.3

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

Acknowledgements

The authors thank the Technical Project of the Department of Education of Jiangxi Province, China, and the Key Technical Project of Yichun Municipality, China, for supporting this work.

References

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