S-Phenethyl (2R,3R)-3-{[(R)-tert-butyl­sulfin­yl]amino}-2-fluoro-3-phenyl­propane­thio­ate

Zhou, Y.-T.; Ren, X.; Li, Y.

doi:10.1107/S2414314618005862

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 4| April 2018| x180586

https://doi.org/10.1107/S2414314618005862

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S-Phenethyl (2R,3R)-3-{[(R)-tert-butylsulfinyl]amino}-2-fluoro-3-phenylpropanethioate

Yi-Tao Zhou,^a Xinfeng Ren ^a and Ya Li ^a ^*

^aDepartment of Chemistry and Chemical Engineering, Shanghai University of Engineering Science, Shanghai, People's Republic of China
^*Correspondence e-mail: ya.li@sues.edu.cn

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 2 April 2018; accepted 16 April 2018; online 19 April 2018)

The title compound, C₂₁H₂₆FNO₂S₂, contains two chiral carbon centres and the absolute configuration has been confirmed as (2R,3R). The dihedral angle between the phenyl rings is 87.1 (2) and the O—C—C—F and F—C—C—N torsion angles are −175.4 (4) and 62.7 (4)°, respectively. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(4) [010] chains and weak C—H⋯O and C—H⋯F interactions cross-link the chains, generating a three-dimensional network.

Keywords: crystal structure; amine; fluorine; thioester; chiral carbon..

CCDC reference: 1837176

Structure description

A chiral carbon atom bearing a fluorine substituent is an important structural motif in many bioactive molecules (Wang et al., 2014 ; Purser et al., 2008 ). Not surprisingly, the synthesis of chiral molecules with a fluorinated carbon center has attracted recent attention (Shang et al., 2015 ; Chen et al., 2017 ). As part of our work in this area, we now describe the synthesis and structure of the title compound (Fig. 1).

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

The fluoro and amino substituents adopt a gauche conformation [F1—C2—C3—N1 = 62.7 (4)°] and the absolute configuration of the chiral carbon centres, C2 and C3, has been confirmed as (R,R). In the crystal, molecules are connected by N—H⋯O hydrogen bonds (Table 1, Fig. 2), generating C(4) [010] chains, with adjacent molecules related by the 2₁ screw axis. Weak C—H⋯O and C—H⋯F interactions cross-link the chains to generate a three-dimensional network.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.80 (2)	2.32 (2)	3.079 (4)	159 (3)
C2—H2⋯O2ⁱ	0.98	2.42	3.265 (4)	144
C10—H10B⋯O1ⁱⁱ	0.97	2.58	3.473 (7)	153
C21—H21B⋯O2ⁱⁱⁱ	0.96	2.57	3.475 (5)	157
C21—H21A⋯F1^iv	0.96	2.55	3.465 (5)	159
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+2]$ ; (ii) $[-x, y+{\script{1\over 2}}, -z+1]$ ; (iii) x, y+1, z; (iv) $[-x, y-{\script{1\over 2}}, -z+2]$ .

Figure 2
Partial packing diagram showing N—H⋯O hydrogen bonds as dashed lines.

Synthesis and crystallization

Potassium bis(trimethylsilyl)amide (1.2 mmol, 1M in toluene) was added slowly to a reaction mixture of (R)-N-benzylidene- 2-methylpropane-2-sulfinamide (209 mg, 1.0 mmol) and S-phenethyl 2-fluoroethanethioate (198 mg, 1.0 mmol) in toluene at 213 K. The reaction mixture was stirred for 1 h at this temperature and then quenched with saturated NH₄Cl/H₂O. The quenched mixture was extracted with EtOAc (20 ml × 3) and the combined organic layers were dried with Na₂SO_4. After removal of the solvent under reduced pressure, the residue was subjected to flash column chromatography to give the title compound (253 mg: yield, 62%). The obtained compound was recrystallized from mixed solvents of ethyl acetate/n-hexane (1:2) to give colorless prisms.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₂₆FNO₂S₂
M_r	407.55
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	293
a, b, c (Å)	13.282 (2), 5.8005 (9), 14.622 (2)
β (°)	106.418 (3)
V (Å³)	1080.6 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.27
Crystal size (mm)	0.20 × 0.16 × 0.13

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2007 )
T_min, T_max	0.641, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	6235, 3783, 3464
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.605

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.121, 1.07
No. of reflections	3783
No. of parameters	239
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)	0.42, −0.20
Absolute structure	Flack x determined using 1338 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.04 (5)
Computer programs: SMART and SAINT (Bruker, 2007), SHELXTL (Sheldrick, 2008 ) and SHELXL2013 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1837176

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618005862/hb4225sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618005862/hb4225Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618005862/hb4225Isup3.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

S-Phenethyl (2R,3R)-3-{[(R)-tert-butylsulfinyl]amino}-2-fluoro-3-phenylpropanethioate top

Crystal data top

C₂₁H₂₆FNO₂S₂	F(000) = 432
M_r = 407.55	D_x = 1.253 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 13.282 (2) Å	Cell parameters from 2551 reflections
b = 5.8005 (9) Å	θ = 5.8–51.0°
c = 14.622 (2) Å	µ = 0.27 mm⁻¹
β = 106.418 (3)°	T = 293 K
V = 1080.6 (3) Å³	Prism, colorless
Z = 2	0.20 × 0.16 × 0.13 mm

Data collection top

Bruker SMART CCD diffractometer	3464 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.023
Absorption correction: multi-scan (SADABS; Bruker, 2007)	θ_max = 25.5°, θ_min = 1.5°
T_min = 0.641, T_max = 0.746	h = −15→16
6235 measured reflections	k = −7→6
3783 independent reflections	l = −17→15

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.047	w = 1/[σ²(F_o²) + (0.070P)² + 0.1132P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.121	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 0.42 e Å⁻³
3783 reflections	Δρ_min = −0.20 e Å⁻³
239 parameters	Absolute structure: Flack x determined using 1338 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
2 restraints	Absolute structure parameter: 0.04 (5)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	U_iso*/U_eq
S1	0.11978 (11)	0.2731 (3)	0.64914 (8)	0.0787 (5)
S2	0.17919 (6)	−0.19558 (15)	1.06022 (6)	0.0398 (2)
F1	0.12082 (17)	0.3427 (4)	0.83432 (15)	0.0532 (6)
N1	0.1447 (2)	0.0152 (5)	0.9803 (2)	0.0408 (7)
O1	0.0356 (3)	−0.1192 (8)	0.6793 (2)	0.0896 (13)
O2	0.0869 (2)	−0.3401 (5)	1.06159 (19)	0.0532 (7)
C1	0.0733 (3)	0.0590 (9)	0.7120 (3)	0.0539 (11)
C2	0.0821 (3)	0.1211 (7)	0.8147 (3)	0.0445 (9)
H2	0.0116	0.1165	0.8233	0.053*
C3	0.1505 (3)	−0.0470 (7)	0.8839 (2)	0.0392 (8)
H3	0.1210	−0.2019	0.8688	0.047*
C4	0.2636 (3)	−0.0500 (7)	0.8796 (2)	0.0411 (8)
C5	0.2989 (3)	−0.2268 (8)	0.8348 (3)	0.0541 (10)
H5	0.2540	−0.3479	0.8088	0.065*
C6	0.4009 (4)	−0.2276 (10)	0.8276 (3)	0.0693 (14)
H6	0.4242	−0.3492	0.7974	0.083*
C7	0.4669 (4)	−0.0499 (11)	0.8648 (3)	0.0666 (13)
H7	0.5352	−0.0504	0.8600	0.080*
C8	0.4333 (3)	0.1275 (10)	0.9090 (3)	0.0611 (12)
H8	0.4786	0.2487	0.9339	0.073*
C9	0.3317 (3)	0.1294 (8)	0.9172 (3)	0.0484 (9)
H9	0.3093	0.2511	0.9480	0.058*
C10	0.0993 (5)	0.1323 (18)	0.5367 (3)	0.108 (3)
H10A	0.0431	0.0209	0.5290	0.129*
H10B	0.0769	0.2459	0.4863	0.129*
C11	0.1951 (6)	0.0108 (14)	0.5253 (4)	0.099 (2)
H11A	0.2147	−0.1100	0.5729	0.119*
H11B	0.1778	−0.0618	0.4630	0.119*
C12	0.2864 (3)	0.1658 (7)	0.5349 (3)	0.0712 (13)
C13	0.3702 (3)	0.1569 (8)	0.6172 (2)	0.096 (2)
H13	0.3716	0.0453	0.6633	0.116*
C14	0.4518 (3)	0.3147 (10)	0.6308 (3)	0.113 (2)
H14	0.5079	0.3086	0.6859	0.135*
C15	0.4497 (3)	0.4814 (9)	0.5620 (4)	0.111 (2)
H15	0.5043	0.5870	0.5711	0.134*
C16	0.3659 (4)	0.4904 (8)	0.4797 (3)	0.115 (2)
H16	0.3645	0.6020	0.4337	0.138*
C17	0.2843 (3)	0.3326 (8)	0.4662 (2)	0.0908 (18)
H17	0.2282	0.3386	0.4111	0.109*
C18	0.2062 (3)	−0.0176 (7)	1.1688 (3)	0.0450 (9)
C19	0.3005 (4)	0.1355 (11)	1.1702 (4)	0.0706 (13)
H19A	0.3246	0.2109	1.2309	0.106*
H19B	0.2801	0.2493	1.1207	0.106*
H19C	0.3560	0.0424	1.1597	0.106*
C20	0.2345 (3)	−0.1915 (11)	1.2502 (3)	0.0635 (11)
H20A	0.2546	−0.1112	1.3100	0.095*
H20B	0.2920	−0.2853	1.2444	0.095*
H20C	0.1749	−0.2877	1.2474	0.095*
C21	0.1111 (3)	0.1219 (8)	1.1702 (3)	0.0541 (10)
H21A	0.0504	0.0241	1.1549	0.081*
H21B	0.1014	0.2435	1.1240	0.081*
H21C	0.1211	0.1870	1.2324	0.081*
H1	0.091 (2)	0.077 (6)	0.981 (2)	0.031 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0949 (9)	0.0960 (12)	0.0526 (6)	−0.0127 (8)	0.0327 (6)	0.0105 (7)
S2	0.0388 (4)	0.0394 (5)	0.0433 (4)	0.0024 (4)	0.0148 (3)	0.0068 (4)
F1	0.0646 (13)	0.0437 (15)	0.0552 (12)	0.0092 (11)	0.0232 (10)	0.0062 (10)
N1	0.0428 (17)	0.0433 (18)	0.0416 (16)	0.0072 (14)	0.0208 (13)	0.0072 (14)
O1	0.110 (3)	0.101 (3)	0.0525 (18)	−0.042 (2)	0.0156 (17)	−0.0191 (19)
O2	0.0562 (16)	0.0516 (17)	0.0524 (15)	−0.0134 (14)	0.0161 (12)	0.0060 (13)
C1	0.042 (2)	0.075 (3)	0.042 (2)	−0.002 (2)	0.0075 (16)	0.002 (2)
C2	0.0374 (18)	0.053 (2)	0.0455 (19)	0.0031 (17)	0.0153 (15)	0.0010 (18)
C3	0.0439 (19)	0.038 (2)	0.0407 (18)	−0.0002 (15)	0.0194 (15)	0.0000 (15)
C4	0.0423 (19)	0.043 (2)	0.0397 (18)	0.0060 (16)	0.0144 (14)	0.0072 (16)
C5	0.063 (2)	0.048 (3)	0.056 (2)	0.010 (2)	0.0252 (18)	0.001 (2)
C6	0.075 (3)	0.069 (3)	0.076 (3)	0.032 (3)	0.041 (2)	0.013 (3)
C7	0.047 (2)	0.090 (4)	0.069 (3)	0.022 (3)	0.027 (2)	0.021 (3)
C8	0.043 (2)	0.081 (3)	0.059 (2)	−0.003 (2)	0.0139 (18)	0.011 (2)
C9	0.046 (2)	0.054 (2)	0.049 (2)	0.0002 (18)	0.0198 (16)	0.0007 (19)
C10	0.094 (4)	0.183 (8)	0.046 (3)	−0.024 (5)	0.020 (3)	0.004 (4)
C11	0.133 (5)	0.102 (5)	0.070 (3)	−0.008 (4)	0.042 (3)	−0.019 (3)
C12	0.083 (3)	0.078 (4)	0.061 (3)	0.011 (3)	0.033 (2)	−0.005 (3)
C13	0.095 (4)	0.127 (6)	0.067 (3)	0.030 (4)	0.024 (3)	0.026 (4)
C14	0.084 (4)	0.162 (7)	0.089 (4)	0.010 (6)	0.020 (3)	0.011 (6)
C15	0.092 (5)	0.126 (6)	0.124 (6)	−0.009 (5)	0.042 (4)	−0.003 (5)
C16	0.119 (5)	0.119 (6)	0.111 (5)	0.011 (5)	0.041 (4)	0.046 (5)
C17	0.096 (4)	0.112 (5)	0.064 (3)	0.009 (4)	0.020 (2)	0.017 (4)
C18	0.0420 (19)	0.050 (2)	0.0416 (19)	−0.0077 (17)	0.0099 (15)	0.0011 (17)
C19	0.056 (3)	0.082 (4)	0.070 (3)	−0.027 (3)	0.012 (2)	−0.008 (3)
C20	0.066 (2)	0.073 (3)	0.0447 (19)	0.000 (3)	0.0049 (16)	0.012 (2)
C21	0.062 (2)	0.052 (2)	0.053 (2)	0.003 (2)	0.0226 (18)	−0.003 (2)

Geometric parameters (Å, º) top

S1—C1	1.758 (5)	C10—H10B	0.9700
S1—C10	1.787 (7)	C11—C12	1.484 (8)
S2—O2	1.489 (3)	C11—H11A	0.9700
S2—N1	1.664 (3)	C11—H11B	0.9700
S2—C18	1.843 (4)	C12—C13	1.3900
F1—C2	1.384 (5)	C12—C17	1.3900
N1—C3	1.477 (4)	C13—C14	1.3900
N1—H1	0.80 (2)	C13—H13	0.9300
O1—C1	1.188 (6)	C14—C15	1.3900
C1—C2	1.516 (5)	C14—H14	0.9300
C2—C3	1.510 (5)	C15—C16	1.3900
C2—H2	0.9800	C15—H15	0.9300
C3—C4	1.522 (5)	C16—C17	1.3900
C3—H3	0.9800	C16—H16	0.9300
C4—C5	1.370 (6)	C17—H17	0.9300
C4—C9	1.387 (6)	C18—C21	1.504 (6)
C5—C6	1.388 (6)	C18—C20	1.523 (6)
C5—H5	0.9300	C18—C19	1.531 (6)
C6—C7	1.363 (8)	C19—H19A	0.9600
C6—H6	0.9300	C19—H19B	0.9600
C7—C8	1.355 (7)	C19—H19C	0.9600
C7—H7	0.9300	C20—H20A	0.9600
C8—C9	1.389 (5)	C20—H20B	0.9600
C8—H8	0.9300	C20—H20C	0.9600
C9—H9	0.9300	C21—H21A	0.9600
C10—C11	1.504 (9)	C21—H21B	0.9600
C10—H10A	0.9700	C21—H21C	0.9600

C1—S1—C10	100.0 (3)	C12—C11—H11A	108.9
O2—S2—N1	111.01 (15)	C10—C11—H11A	108.9
O2—S2—C18	105.33 (16)	C12—C11—H11B	108.9
N1—S2—C18	98.15 (17)	C10—C11—H11B	108.9
C3—N1—S2	114.4 (2)	H11A—C11—H11B	107.7
C3—N1—H1	114 (3)	C13—C12—C17	120.0
S2—N1—H1	113 (3)	C13—C12—C11	119.5 (4)
O1—C1—C2	120.8 (4)	C17—C12—C11	120.3 (4)
O1—C1—S1	125.0 (4)	C12—C13—C14	120.0
C2—C1—S1	114.2 (3)	C12—C13—H13	120.0
F1—C2—C3	110.1 (3)	C14—C13—H13	120.0
F1—C2—C1	110.3 (3)	C15—C14—C13	120.0
C3—C2—C1	112.0 (3)	C15—C14—H14	120.0
F1—C2—H2	108.1	C13—C14—H14	120.0
C3—C2—H2	108.1	C14—C15—C16	120.0
C1—C2—H2	108.1	C14—C15—H15	120.0
N1—C3—C2	107.3 (3)	C16—C15—H15	120.0
N1—C3—C4	111.1 (3)	C17—C16—C15	120.0
C2—C3—C4	113.1 (3)	C17—C16—H16	120.0
N1—C3—H3	108.4	C15—C16—H16	120.0
C2—C3—H3	108.4	C16—C17—C12	120.0
C4—C3—H3	108.4	C16—C17—H17	120.0
C5—C4—C9	118.6 (4)	C12—C17—H17	120.0
C5—C4—C3	120.3 (4)	C21—C18—C20	111.7 (3)
C9—C4—C3	121.1 (3)	C21—C18—C19	112.0 (4)
C4—C5—C6	120.9 (5)	C20—C18—C19	110.7 (3)
C4—C5—H5	119.6	C21—C18—S2	110.6 (2)
C6—C5—H5	119.6	C20—C18—S2	104.3 (3)
C7—C6—C5	119.9 (5)	C19—C18—S2	107.2 (3)
C7—C6—H6	120.1	C18—C19—H19A	109.5
C5—C6—H6	120.1	C18—C19—H19B	109.5
C8—C7—C6	120.2 (4)	H19A—C19—H19B	109.5
C8—C7—H7	119.9	C18—C19—H19C	109.5
C6—C7—H7	119.9	H19A—C19—H19C	109.5
C7—C8—C9	120.4 (5)	H19B—C19—H19C	109.5
C7—C8—H8	119.8	C18—C20—H20A	109.5
C9—C8—H8	119.8	C18—C20—H20B	109.5
C4—C9—C8	120.0 (4)	H20A—C20—H20B	109.5
C4—C9—H9	120.0	C18—C20—H20C	109.5
C8—C9—H9	120.0	H20A—C20—H20C	109.5
C11—C10—S1	113.7 (4)	H20B—C20—H20C	109.5
C11—C10—H10A	108.8	C18—C21—H21A	109.5
S1—C10—H10A	108.8	C18—C21—H21B	109.5
C11—C10—H10B	108.8	H21A—C21—H21B	109.5
S1—C10—H10B	108.8	C18—C21—H21C	109.5
H10A—C10—H10B	107.7	H21A—C21—H21C	109.5
C12—C11—C10	113.5 (6)	H21B—C21—H21C	109.5

O2—S2—N1—C3	−89.5 (3)	C6—C7—C8—C9	0.4 (7)
C18—S2—N1—C3	160.6 (3)	C5—C4—C9—C8	0.1 (6)
C10—S1—C1—O1	−3.1 (5)	C3—C4—C9—C8	−177.3 (3)
C10—S1—C1—C2	178.4 (3)	C7—C8—C9—C4	−0.5 (6)
O1—C1—C2—F1	−175.4 (4)	C1—S1—C10—C11	−95.7 (6)
S1—C1—C2—F1	3.2 (4)	S1—C10—C11—C12	−59.0 (7)
O1—C1—C2—C3	61.6 (5)	C10—C11—C12—C13	106.0 (5)
S1—C1—C2—C3	−119.8 (3)	C10—C11—C12—C17	−68.3 (5)
S2—N1—C3—C2	159.9 (2)	C17—C12—C13—C14	0.0
S2—N1—C3—C4	−75.9 (3)	C11—C12—C13—C14	−174.4 (4)
F1—C2—C3—N1	62.7 (4)	C12—C13—C14—C15	0.0
C1—C2—C3—N1	−174.2 (3)	C13—C14—C15—C16	0.0
F1—C2—C3—C4	−60.2 (4)	C14—C15—C16—C17	0.0
C1—C2—C3—C4	62.8 (4)	C15—C16—C17—C12	0.0
N1—C3—C4—C5	135.5 (4)	C13—C12—C17—C16	0.0
C2—C3—C4—C5	−103.6 (4)	C11—C12—C17—C16	174.3 (4)
N1—C3—C4—C9	−47.1 (4)	O2—S2—C18—C21	−57.3 (3)
C2—C3—C4—C9	73.7 (4)	N1—S2—C18—C21	57.2 (3)
C9—C4—C5—C6	0.4 (6)	O2—S2—C18—C20	62.9 (3)
C3—C4—C5—C6	177.8 (4)	N1—S2—C18—C20	177.4 (3)
C4—C5—C6—C7	−0.5 (7)	O2—S2—C18—C19	−179.7 (3)
C5—C6—C7—C8	0.1 (7)	N1—S2—C18—C19	−65.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.80 (2)	2.32 (2)	3.079 (4)	159 (3)
C2—H2···O2ⁱ	0.98	2.42	3.265 (4)	144
C10—H10B···O1ⁱⁱ	0.97	2.58	3.473 (7)	153
C21—H21B···O2ⁱⁱⁱ	0.96	2.57	3.475 (5)	157
C21—H21A···F1^iv	0.96	2.55	3.465 (5)	159

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

Funding information

The authors thank the Innovation Program of Shanghai University Students (cx1704001) for financial support.

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