2-Amino-6-methyl-1,3-benzothia­zole–deca­nedioic acid (2/1)

Shi, X.-J.; Wang, Z.-C.; Chen, Q.; Zhao, X.-J.

doi:10.1107/S1600536809031857

organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Page o2188

doi:10.1107/S1600536809031857

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2-Amino-6-methyl-1,3-benzothiazole–decanedioic acid (2/1)

Xiang-Jun Shi,^a Zhi-Chao Wang,^a Qiang Chen ^a and Xiao-Jun Zhao ^a ^*

^aCollege of Chemistry and Life Science, Tianjin Key Laboratory of Structure and Performance of Functional Molecule, Tianjin Normal University, Tianjin 300387, People's Republic of China
^*Correspondence e-mail: xiaojun_zhao15@yahoo.com.cn

(Received 11 August 2009; accepted 12 August 2009; online 19 August 2009)

Co-crystallization of 2-amino-6-methyl-1,3-benzothiazole with decanedioic acid under hydrothermal conditions afforded the title 2:1 co-crystal, 2C₈H₈N₂S·C₁₀H₁₈O₄. The decanedioic acid molecule is located on an inversion centre. In the crystal, intermolecular N—H⋯O and O—H⋯O hydrogen bonds connect the components into a two-dimensional wave-like layer structure extending parallel to (100).

Related literature

For molecular self-assembly and crystal engineering, see: Sun & Cui (2008 ); Hunter (1993 ); Yang et al. (2005 ). For the solid structures and properties of metal complexes of aminobenzothiazole and its derivatives, see: Lynch et al. (1998 , 1999 ); Sun & Cui (2008); Popović et al. (2002 ); Antiñolo et al. (2007 ); Dong et al. (2002 ); Chen et al. (2008 ); Zhang et al. (2009 ). For the structures of decanedioic acid-based metal complexes and co-crystals, see: Xian et al. (2009 ); Braga et al. (2006 ); Aakeröy et al. (2007 ).

Experimental

Crystal data

2C₈H₈N₂S·C₁₀H₁₈O₄
M_r = 530.71
Monoclinic, P 2₁ /n
a = 5.3791 (5) Å
b = 21.822 (2) Å
c = 11.9431 (11) Å
β = 91.6660 (10)°
V = 1401.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 293 K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.931, T_max = 0.952
7545 measured reflections
2470 independent reflections
1822 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.05
2470 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.78	2.597 (2)	171
N2—H2A⋯O2	0.86	2.09	2.914 (2)	161
N2—H2B⋯O1ⁱ	0.86	2.14	2.954 (2)	157
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2001 ); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809031857/bt5031sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809031857/bt5031Isup2.hkl

checkCIF report

Comment top

During the past decades, molecular self-/assembly by classical coordination bonds and/or intermolecular non-covalent interactions such as hydrogen-bonding, π···π stacking, electrostatic interactions and so on, has been becoming more and more attractive in biology, biochemistry and new material fields (Sun et al., 2008; Hunter, 1993; Yang et al., 2005).

Acting as one of the excellent building blocks with multiple hydrogen-bonding sites and metal ion binding donors, aminobenzothiazole and its derivatives have been extensively utilized in the new materials, biochemistry and agriculture chemistry, due to the lower toxicity, high biological activity as well as excellent chemical reactivity (Lynch et al., 1998; Lynch et al., 1999; Sun et al., 2008; Popović et al., 2002; Antiñolo et al., 2007; Dong et al., 2002; Chen et al., 2008). On the other hand, the long decanedioic acid with adjustable deprotonated form and flexible aliphatic chain has also exhibited novel functions such as dianion templating (Xian et al., 2009) and heterosynthons with nitrogen-containing compounds (Braga et al., 2006; Aakeröy et al., 2007) in the fields of metal complexes and molecular co-crystals.

Thus, as a continuation of molecular assembly behavior in the solid state, in the present paper, the rigid 2-amino-6-methyl-1,3-benzothiazole (Ambt) and flexible decanedioic acid were selected as building blocks to cocrystallize. As a result, an intermolecular hydrogen bonded adduct, (I), was obtained under the hydrothermal conditions.

As shown in Fig. 1, the asymmetric unit of (I) comprises one neutral Ambt molecule with no crystallographically imposed symmetry and half a decanedioic acid located on a centre of inversion. Obviously, no proton transfer was observed for the neutral cocrystal, which is much different from the 2-aminobenzothiazolium 2,4-dicarboxybenzoate monohydrate (Zhang et al., 2009). The exocyclic amino group of Ambt is roughly coplanar with the benzothiazole ring. Similarily, the carboxylic residues of decanedioic acid are also co-planar with their long aliphatic chain. In the packing structure of I, two pairs of the intermolecuar O1—H1 ···N1 and N2—H2A ···O2 hydrogen-bonding interactions (Table 1) connect the two Ambt molecules and one decanedioic acid.

Related literature top

For molecular self-assembly and crystal engineering, see: Sun et al. (2008); Hunter (1993); Yang et al. (2005). For the solid structures and properties of metal complexes of aminobenzothiazole and its derivatives, see: Lynch et al. (1998, 1999); Sun et al. (2008); Popović et al. (2002); Antiñolo et al. (2007); Dong et al. (2002); Chen et al. (2008); Zhang et al. (2009). For the structures of decanedioic acid-based metal complexes and co-crystals, see: Xian et al. (2009); Braga et al. (2006); Aakeröy et al. (2007).

Experimental top

To an aqueous solution of Ambt (40.4 mg, 0.2 mmol) was slowly added an aqueous solution of decanedioic acid (20.2 mg, 0.1 mmol) with constant stirring. After further stirring for about ten minutes, the resulting mixture was sealed in a stainless steel vessel and heated at 140 ^oC for 3 days. After the mixture was cooled to room temperature at a rate of 5 ^oC / h, pale-yellow block-shaped crystals suitable for X-ray diffraction were obtained directly, washed with ethanol and dried in air.Yield: 34% based on Ambt. Anal. calcd for C₁₃H₁₇N₂O₂S: C, 58.84; H, 6.46; N, 10.56%. Found: C, 58.78; H, 6.56; N,10.70%.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawnat the 30% probability level. The dashed lines indicate intermolecular hydrogen bonds.[Symmetry code: (A) 4 – x, 1 – y, – z]
	Fig. 2. The two-dimensional layer of (I) formed by N–H···O and O–H ···O hydrogen bonding interactions.

2-Amino-6-methyl-1,3-benzothiazole–decanedioic acid (2/1) top

Crystal data top

2C₈H₈N₂S·C₁₀H₁₈O₄	F(000) = 564
M_r = 530.71	D_x = 1.258 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 5.3791 (5) Å	Cell parameters from 1765 reflections
b = 21.822 (2) Å	θ = 2.5–22.8°
c = 11.9431 (11) Å	µ = 0.23 mm⁻¹
β = 91.666 (1)°	T = 293 K
V = 1401.3 (2) Å³	Block, pale-yellow
Z = 2	0.32 × 0.24 × 0.22 mm

Data collection top

Bruker APEXII CCD area-detector diffractometer	2470 independent reflections
Radiation source: fine-focus sealed tube	1822 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
T_min = 0.931, T_max = 0.952	k = −25→21
7545 measured reflections	l = −14→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0483P)² + 0.3107P] where P = (F_o² + 2F_c²)/3
2470 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

2C₈H₈N₂S·C₁₀H₁₈O₄	V = 1401.3 (2) Å³
M_r = 530.71	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.3791 (5) Å	µ = 0.23 mm⁻¹
b = 21.822 (2) Å	T = 293 K
c = 11.9431 (11) Å	0.32 × 0.24 × 0.22 mm
β = 91.666 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	2470 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1822 reflections with I > 2σ(I)
T_min = 0.931, T_max = 0.952	R_int = 0.024
7545 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.05	Δρ_max = 0.23 e Å⁻³
2470 reflections	Δρ_min = −0.26 e Å⁻³
164 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
S1	0.47667 (11)	0.17050 (3)	0.20230 (5)	0.0647 (2)
O1	1.1513 (3)	0.27012 (7)	−0.03449 (11)	0.0595 (4)
H1	1.0456	0.2531	0.0026	0.089*
O2	1.2105 (3)	0.32343 (7)	0.12223 (12)	0.0662 (4)
N1	0.8009 (3)	0.21067 (7)	0.06387 (13)	0.0502 (4)
N2	0.8217 (3)	0.25824 (8)	0.23838 (14)	0.0628 (5)
H2A	0.9420	0.2815	0.2189	0.075*
H2B	0.7643	0.2610	0.3046	0.075*
C1	0.7248 (4)	0.21790 (9)	0.16608 (16)	0.0495 (5)
C2	0.4781 (4)	0.13827 (9)	0.06865 (17)	0.0536 (5)
C3	0.3269 (4)	0.09285 (10)	0.02272 (19)	0.0658 (6)
H3A	0.2024	0.0754	0.0648	0.079*
C4	0.3619 (4)	0.07353 (10)	−0.0861 (2)	0.0647 (6)
C5	0.5474 (4)	0.10135 (11)	−0.14663 (18)	0.0650 (6)
H5A	0.5703	0.0889	−0.2201	0.078*
C6	0.6984 (4)	0.14661 (10)	−0.10228 (17)	0.0599 (6)
H6A	0.8214	0.1643	−0.1449	0.072*
C7	0.6645 (4)	0.16541 (9)	0.00673 (16)	0.0488 (5)
C8	0.1999 (6)	0.02374 (13)	−0.1383 (2)	0.0920 (9)
H8A	0.0819	0.0101	−0.0850	0.138*
H8B	0.3023	−0.0101	−0.1597	0.138*
H8C	0.1130	0.0397	−0.2033	0.138*
C9	1.2624 (4)	0.31276 (9)	0.02632 (16)	0.0469 (5)
C10	1.4559 (4)	0.34752 (9)	−0.03539 (16)	0.0511 (5)
H10A	1.3758	0.3681	−0.0987	0.061*
H10B	1.5740	0.3185	−0.0648	0.061*
C11	1.5968 (4)	0.39443 (9)	0.03408 (16)	0.0509 (5)
H11A	1.6931	0.3735	0.0924	0.061*
H11B	1.4788	0.4210	0.0701	0.061*
C12	1.7698 (4)	0.43316 (9)	−0.03430 (17)	0.0517 (5)
H12A	1.8855	0.4064	−0.0713	0.062*
H12B	1.6726	0.4544	−0.0920	0.062*
C13	1.9159 (4)	0.47985 (9)	0.03387 (16)	0.0511 (5)
H13A	2.0164	0.4585	0.0901	0.061*
H13B	1.8000	0.5058	0.0727	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0678 (4)	0.0744 (4)	0.0529 (3)	−0.0197 (3)	0.0191 (3)	0.0042 (3)
O1	0.0673 (10)	0.0637 (9)	0.0484 (8)	−0.0271 (7)	0.0198 (7)	−0.0071 (7)
O2	0.0763 (11)	0.0750 (10)	0.0484 (8)	−0.0275 (8)	0.0207 (7)	−0.0107 (7)
N1	0.0517 (10)	0.0565 (10)	0.0428 (9)	−0.0120 (8)	0.0086 (7)	0.0036 (7)
N2	0.0740 (13)	0.0691 (12)	0.0460 (9)	−0.0193 (10)	0.0129 (9)	−0.0042 (9)
C1	0.0512 (12)	0.0513 (11)	0.0464 (11)	−0.0036 (9)	0.0074 (9)	0.0084 (9)
C2	0.0538 (12)	0.0549 (12)	0.0524 (11)	−0.0087 (10)	0.0061 (9)	0.0091 (10)
C3	0.0606 (14)	0.0675 (14)	0.0695 (14)	−0.0214 (12)	0.0070 (11)	0.0113 (12)
C4	0.0671 (15)	0.0618 (13)	0.0646 (14)	−0.0132 (12)	−0.0080 (11)	0.0024 (11)
C5	0.0712 (15)	0.0740 (15)	0.0497 (12)	−0.0096 (12)	−0.0002 (11)	−0.0010 (11)
C6	0.0615 (14)	0.0691 (14)	0.0495 (12)	−0.0136 (11)	0.0063 (10)	0.0034 (10)
C7	0.0482 (12)	0.0515 (11)	0.0465 (11)	−0.0050 (9)	0.0012 (9)	0.0087 (9)
C8	0.097 (2)	0.0889 (19)	0.0893 (18)	−0.0331 (17)	−0.0044 (16)	−0.0102 (16)
C9	0.0476 (12)	0.0457 (11)	0.0477 (11)	−0.0043 (9)	0.0069 (9)	0.0008 (9)
C10	0.0518 (12)	0.0497 (11)	0.0525 (12)	−0.0099 (9)	0.0122 (9)	−0.0013 (9)
C11	0.0491 (12)	0.0511 (12)	0.0527 (11)	−0.0076 (9)	0.0057 (9)	0.0029 (9)
C12	0.0474 (12)	0.0519 (12)	0.0561 (12)	−0.0085 (9)	0.0078 (9)	−0.0001 (9)
C13	0.0482 (12)	0.0515 (12)	0.0538 (11)	−0.0069 (9)	0.0053 (9)	0.0040 (9)

Geometric parameters (Å, º) top

S1—C2	1.744 (2)	C6—C7	1.382 (3)
S1—C1	1.753 (2)	C6—H6A	0.9300
O1—C9	1.313 (2)	C8—H8A	0.9600
O1—H1	0.8200	C8—H8B	0.9600
O2—C9	1.209 (2)	C8—H8C	0.9600
N1—C1	1.308 (2)	C9—C10	1.499 (3)
N1—C7	1.397 (2)	C10—C11	1.508 (3)
N2—C1	1.329 (2)	C10—H10A	0.9700
N2—H2A	0.8600	C10—H10B	0.9700
N2—H2B	0.8600	C11—C12	1.514 (3)
C2—C3	1.385 (3)	C11—H11A	0.9700
C2—C7	1.395 (3)	C11—H11B	0.9700
C3—C4	1.385 (3)	C12—C13	1.510 (3)
C3—H3A	0.9300	C12—H12A	0.9700
C4—C5	1.388 (3)	C12—H12B	0.9700
C4—C8	1.516 (3)	C13—C13ⁱ	1.513 (4)
C5—C6	1.375 (3)	C13—H13A	0.9700
C5—H5A	0.9300	C13—H13B	0.9700

C2—S1—C1	89.34 (9)	C4—C8—H8C	109.5
C9—O1—H1	109.5	H8A—C8—H8C	109.5
C1—N1—C7	111.53 (16)	H8B—C8—H8C	109.5
C1—N2—H2A	120.0	O2—C9—O1	123.13 (17)
C1—N2—H2B	120.0	O2—C9—C10	123.42 (18)
H2A—N2—H2B	120.0	O1—C9—C10	113.44 (16)
N1—C1—N2	123.95 (18)	C9—C10—C11	114.71 (16)
N1—C1—S1	114.85 (15)	C9—C10—H10A	108.6
N2—C1—S1	121.18 (15)	C11—C10—H10A	108.6
C3—C2—C7	121.1 (2)	C9—C10—H10B	108.6
C3—C2—S1	129.25 (16)	C11—C10—H10B	108.6
C7—C2—S1	109.65 (15)	H10A—C10—H10B	107.6
C4—C3—C2	119.7 (2)	C10—C11—C12	112.90 (16)
C4—C3—H3A	120.2	C10—C11—H11A	109.0
C2—C3—H3A	120.2	C12—C11—H11A	109.0
C3—C4—C5	118.4 (2)	C10—C11—H11B	109.0
C3—C4—C8	120.8 (2)	C12—C11—H11B	109.0
C5—C4—C8	120.8 (2)	H11A—C11—H11B	107.8
C6—C5—C4	122.6 (2)	C13—C12—C11	113.84 (16)
C6—C5—H5A	118.7	C13—C12—H12A	108.8
C4—C5—H5A	118.7	C11—C12—H12A	108.8
C5—C6—C7	118.9 (2)	C13—C12—H12B	108.8
C5—C6—H6A	120.6	C11—C12—H12B	108.8
C7—C6—H6A	120.6	H12A—C12—H12B	107.7
C6—C7—C2	119.34 (19)	C12—C13—C13ⁱ	114.4 (2)
C6—C7—N1	126.03 (18)	C12—C13—H13A	108.7
C2—C7—N1	114.63 (17)	C13ⁱ—C13—H13A	108.7
C4—C8—H8A	109.5	C12—C13—H13B	108.7
C4—C8—H8B	109.5	C13ⁱ—C13—H13B	108.7
H8A—C8—H8B	109.5	H13A—C13—H13B	107.6

C7—N1—C1—N2	−179.62 (19)	C5—C6—C7—C2	−0.2 (3)
C7—N1—C1—S1	−0.5 (2)	C5—C6—C7—N1	−179.8 (2)
C2—S1—C1—N1	0.29 (17)	C3—C2—C7—C6	0.0 (3)
C2—S1—C1—N2	179.42 (18)	S1—C2—C7—C6	−179.96 (17)
C1—S1—C2—C3	−180.0 (2)	C3—C2—C7—N1	179.69 (19)
C1—S1—C2—C7	0.02 (16)	S1—C2—C7—N1	−0.3 (2)
C7—C2—C3—C4	0.5 (3)	C1—N1—C7—C6	−179.8 (2)
S1—C2—C3—C4	−179.45 (19)	C1—N1—C7—C2	0.5 (3)
C2—C3—C4—C5	−0.9 (4)	O2—C9—C10—C11	4.3 (3)
C2—C3—C4—C8	179.8 (2)	O1—C9—C10—C11	−176.76 (17)
C3—C4—C5—C6	0.8 (4)	C9—C10—C11—C12	−173.70 (17)
C8—C4—C5—C6	−179.9 (2)	C10—C11—C12—C13	−179.12 (17)
C4—C5—C6—C7	−0.2 (4)	C11—C12—C13—C13ⁱ	−178.3 (2)

Symmetry code: (i) −x+4, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.78	2.597 (2)	171
N2—H2A···O2	0.86	2.09	2.914 (2)	161
N2—H2B···O1ⁱⁱ	0.86	2.14	2.954 (2)	157

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

Experimental details

Crystal data
Chemical formula	2C₈H₈N₂S·C₁₀H₁₈O₄
M_r	530.71
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.3791 (5), 21.822 (2), 11.9431 (11)
β (°)	91.666 (1)
V (Å³)	1401.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.23
Crystal size (mm)	0.32 × 0.24 × 0.22

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.931, 0.952
No. of measured, independent and observed [I > 2σ(I)] reflections	7545, 2470, 1822
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.05
No. of reflections	2470
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.26

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg & Berndt, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.78	2.597 (2)	171.3
N2—H2A···O2	0.86	2.09	2.914 (2)	161.2
N2—H2B···O1ⁱ	0.86	2.14	2.954 (2)	157.1

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

Acknowledgements

The authors gratefully acknowledge financial support from Tianjin Normal University.

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