Bis[μ-bis­(pyridin-2-yl)methanone oxime-κ3N:,N′,N′′]bis­[di­acetato-κ2O,O′;κO-zinc(II)]

Crundwell, G.; Crundwell, N.E.; Westcott, B.L.

doi:10.1107/S2414314624001226

metal-organic compounds

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ISSN: 2414-3146

Volume 9| Part 2| February 2024| x240122

https://doi.org/10.1107/S2414314624001226

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Bis[μ-bis(pyridin-2-yl)methanone oxime-κ³N:,N′,N′′]bis[diacetato-κ²O,O′;κO-zinc(II)]

Guy Crundwell,^a ^* Nigel E. Crundwell ^a and Barry L. Westcott ^a

^aCentral Connecticut State University, Department of Chemistry & Biochemistry, 1619 Stanley Street, New Britain, CT 06053, USA
^*Correspondence e-mail: crundwellg@ccsu.edu

Edited by M. Zeller, Purdue University, USA (Received 23 January 2024; accepted 5 February 2024; online 16 February 2024)

The structure of the title complex, [Zn₂(C₂H₃O₂)₄(C₁₁H₉N₃O)₂], is triclinic containing half of the molecule in the asymmetric unit. Each zinc atom is coordinated to a pyridyl and oxime nitrogen from one di-2-pyridyl ketone oxime (dpko) ligand and a third nitrogen from the other dpko pyridyl ring. Additionally, each zinc is coordinated to two acetato anions, one of which is bidentate and the other monodentate. The uncoordinated oxygen of the monodentate acetato group is involved in a hydrogen bond with the oxime hydrogen. The packing in the crystal is assisted by weak C—H⋯O interactions between acetato groups and neighboring pyridyl rings.

Keywords: crystal structure; dpko; zinc.

CCDC reference: 2331143

Structure description

The three N atoms in dpko can act as ligands in a variety of ways. Previous reactions of Zn^II with dpko led to molecules of the form Zn(dpko)Cl₂ (Alexiou et al., 2003 ; Gökce et al., 2019 ) and Zn(dpko)Br₂ (Westcott et al., 2016 ) where both pyridyl N atoms are bonding to the metal and the oxime group is directed away from the metal center. Dpko ligands with zinc have also been shown to retain their bidentate nature, yet they opt to bond via one pyridyl nitrogen and the oxime nitrogen (Tarushi et al., 2013 ). Finally, in this complex a third motif is seen; one where a pyridyl nitrogen and oxime nitrogen bond to one zinc and the other pyridyl nitrogen binds to another. In this case a dimer is made and is analogous to Cu²⁺ complexes with dpko (Goher & Mautner, 1999 ) and to Mg²⁺ complexes with dpko (Milios et al., 2005 ).

The asymmetric-unit of the the title complex, Fig. 1, comprises one-half molecule with the full molecule generated by inversion symmetry. Two acetate anions are also coordinated to the zinc. The first acetato group bonds with both O atoms at bond lengths of 2.1369 (17) and 2.289 (2) Å and the second acetato group coordinates through one oxygen at 2.0513 (14) Å. The second oxygen on the monodentate acetate is hydrogen bonded to the hydrogen on the oxime, Table 1. The packing in the crystal is assisted by weak C—H⋯O interactions between acetato groups and neighboring pyridyl rings(Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O5	1.11 (4)	1.32 (4)	2.428 (2)	176 (3)
C2—H2⋯O1ⁱⁱ	0.93	2.34	3.245 (2)	164
C3—H3⋯O3ⁱⁱⁱ	0.93	2.58	3.293 (3)	134
C9—H9⋯03^iv	0.93	2.59	3.361 (3)	141
C11—H11⋯O2ⁱ	0.93	2.38	2.941 (3)	119
Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

Figure 1
An ORTEP style (Farrugia, 2012

) view of the title compound. Displacement ellipsoids are drawn at the 50% probability level. All hydrogen atoms not involved in hydrogen bonding have been omitted and non-H atoms generated by the inversion center have not been labeled.

Synthesis and crystallization

Zinc acetate dihydrate and di-2-pyridyl ketone oxime (dpko) were used as received from Mallinckrodt and Sigma-Aldrich, respectively. A 15 ml solution of 0.3474 g (1.58 mmol) of zinc acetate dihydrate in acetonitrile was combined with a 15 ml acetonitrile solution of 0.3227 g (1.62 mmol) of dpko and stirred for 10 minutes, producing a colorless solution. Diffraction-quality, colorless crystals formed via slow evaporation of solvent within 24 h. Crystals were harvested from the evaporating solutions and decompose upon heating. IR (cm⁻¹) 1960(wb), 1710(mb), 1590(s), 1560(s), 1480(m), 1420(s), 1300(w), 1210(w), 1110(w), 1080(sb), 1010(s), 789(s), 754(m), 698(m), 675(m), 659(s).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	[Zn₂(C₂H₃O₂)₄(C₁₁H₉N₃O)₂]
M_r	765.34
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	8.3549 (7), 9.3366 (8), 12.3971 (7)
α, β, γ (°)	69.409 (7), 75.524 (6), 65.217 (8)
V (Å³)	815.88 (13)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	1.54
Crystal size (mm)	0.35 × 0.32 × 0.31

Data collection
Diffractometer	Xcalibur, Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.907, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	10420, 5737, 4546
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.778

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.098, 1.03
No. of reflections	5737
No. of parameters	223
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.66, −0.22
Computer programs: CrysAlis PRO (Rigaku OD, 2019 $[Rigaku OD (2019). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXS (Sheldrick, 2008 ), SHELXL (Sheldrick, 2015 ), and OLEX2 (Dolomanov et al., 2009 ).

Structural data

CCDC reference: 2331143

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314624001226/zl4065sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314624001226/zl4065Isup2.hkl

checkCIF report

Computing details top

Bis[µ-bis(pyridin-2-yl)methanone oxime-κ³N:N',N'']bis[diacetato-κ²O,O';κO-zinc(II)] top

Crystal data top

[Zn₂(C₂H₃O₂)₄(C₁₁H₉N₃O)₂]	Z = 1
M_r = 765.34	F(000) = 392
Triclinic, P1	D_x = 1.558 Mg m⁻³
a = 8.3549 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.3366 (8) Å	Cell parameters from 4170 reflections
c = 12.3971 (7) Å	θ = 4.5–33.0°
α = 69.409 (7)°	µ = 1.54 mm⁻¹
β = 75.524 (6)°	T = 293 K
γ = 65.217 (8)°	Block, colorless
V = 815.88 (13) Å³	0.35 × 0.32 × 0.31 mm

Data collection top

Xcalibur, Sapphire3 diffractometer	5737 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4546 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
Detector resolution: 16.1790 pixels mm^-1	θ_max = 33.6°, θ_min = 4.2°
ω scans	h = −11→12
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2019)	k = −13→13
T_min = 0.907, T_max = 1.000	l = −18→18
10420 measured reflections

Refinement top

Refinement on F²	Primary atom site location: iterative
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0443P)² + 0.1935P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
5737 reflections	Δρ_max = 0.66 e Å⁻³
223 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints

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.

Refinement. Hydrogen atoms on sp2 and sp3 carbons were placed at calculated positions with a C—H distance of 0.93?Å and 0.96?Å and were included in the refinement in riding motion approximation with Uiso = 1.2Ueq or 1.5Ueq of the carrier atom, respectively. The position and thermal parameters for the oxime hydrogen were allowed to refine freely.

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

	x	y	z	U_iso*/U_eq
Zn1	0.34622 (3)	0.46689 (2)	0.21836 (2)	0.03562 (8)
O1	0.3171 (2)	0.81600 (16)	0.04557 (12)	0.0489 (4)
O2	0.2284 (2)	0.3158 (2)	0.35870 (14)	0.0625 (4)
O3	0.0490 (3)	0.5591 (2)	0.28225 (15)	0.0738 (5)
O4	0.4272 (2)	0.56182 (17)	0.31195 (12)	0.0517 (4)
O5	0.3442 (3)	0.83015 (19)	0.23171 (15)	0.0721 (6)
N1	0.3011 (2)	0.38026 (17)	0.08947 (13)	0.0362 (3)
N2	0.3064 (2)	0.66897 (16)	0.06028 (12)	0.0338 (3)
N3	0.3964 (2)	0.73732 (16)	−0.23140 (12)	0.0327 (3)
C1	0.2935 (3)	0.2329 (2)	0.10808 (19)	0.0475 (5)
H1A	0.318212	0.155161	0.179385	0.057*
C2	0.2505 (3)	0.1924 (2)	0.0253 (2)	0.0549 (6)
H2	0.247728	0.088449	0.040771	0.066*
C3	0.2119 (3)	0.3053 (3)	−0.0797 (2)	0.0523 (5)
H3	0.180763	0.280147	−0.135924	0.063*
C4	0.2202 (3)	0.4589 (2)	−0.10074 (17)	0.0410 (4)
H4	0.194267	0.538517	−0.171163	0.049*
C5	0.2675 (2)	0.49042 (19)	−0.01513 (14)	0.0314 (3)
C6	0.2823 (2)	0.64842 (18)	−0.03036 (13)	0.0300 (3)
C7	0.2681 (2)	0.77575 (19)	−0.14482 (14)	0.0310 (3)
C8	0.1286 (3)	0.9258 (2)	−0.15985 (17)	0.0434 (4)
H8	0.042857	0.949951	−0.097911	0.052*
C9	0.1179 (3)	1.0396 (2)	−0.26807 (19)	0.0523 (5)
H9	0.025274	1.141321	−0.279936	0.063*
C10	0.2468 (3)	0.9997 (2)	−0.35777 (18)	0.0489 (5)
H10	0.241831	1.073160	−0.431699	0.059*
C11	0.3830 (3)	0.8493 (2)	−0.33611 (15)	0.0419 (4)
H11	0.470518	0.823590	−0.396915	0.050*
C12	0.0764 (3)	0.4213 (3)	0.35166 (18)	0.0533 (5)
C13	−0.0764 (4)	0.3756 (5)	0.4298 (3)	0.0938 (12)
H13A	−0.181804	0.435492	0.391611	0.141*
H13B	−0.096138	0.402581	0.501117	0.141*
H13C	−0.047996	0.259790	0.446085	0.141*
C14	0.4072 (3)	0.7035 (2)	0.30937 (16)	0.0426 (4)
C15	0.4641 (4)	0.7266 (3)	0.4055 (2)	0.0684 (7)
H15A	0.461453	0.638302	0.474543	0.103*
H15B	0.384817	0.829313	0.420185	0.103*
H15C	0.582636	0.726925	0.383512	0.103*
H1	0.325 (5)	0.821 (4)	0.132 (3)	0.116 (13)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.04561 (13)	0.02653 (10)	0.02801 (10)	−0.00898 (8)	−0.00571 (8)	−0.00425 (7)
O1	0.0854 (11)	0.0274 (6)	0.0412 (7)	−0.0243 (7)	−0.0195 (7)	−0.0054 (5)
O2	0.0476 (9)	0.0701 (11)	0.0524 (9)	−0.0126 (8)	−0.0018 (7)	−0.0110 (8)
O3	0.0920 (14)	0.0576 (11)	0.0510 (10)	−0.0185 (10)	−0.0065 (9)	−0.0037 (8)
O4	0.0768 (11)	0.0382 (7)	0.0431 (7)	−0.0183 (7)	−0.0202 (7)	−0.0095 (6)
O5	0.1310 (17)	0.0374 (8)	0.0516 (9)	−0.0177 (9)	−0.0432 (10)	−0.0107 (7)
N1	0.0459 (8)	0.0255 (6)	0.0353 (7)	−0.0141 (6)	−0.0083 (6)	−0.0028 (5)
N2	0.0482 (8)	0.0231 (6)	0.0302 (6)	−0.0126 (6)	−0.0065 (6)	−0.0068 (5)
N3	0.0411 (8)	0.0261 (6)	0.0263 (6)	−0.0082 (6)	−0.0082 (5)	−0.0043 (5)
C1	0.0612 (12)	0.0276 (8)	0.0519 (11)	−0.0198 (8)	−0.0135 (10)	0.0001 (7)
C2	0.0700 (15)	0.0314 (9)	0.0726 (15)	−0.0253 (10)	−0.0184 (12)	−0.0104 (9)
C3	0.0655 (14)	0.0443 (11)	0.0614 (13)	−0.0246 (10)	−0.0176 (11)	−0.0188 (9)
C4	0.0533 (11)	0.0351 (9)	0.0398 (9)	−0.0190 (8)	−0.0126 (8)	−0.0083 (7)
C5	0.0364 (8)	0.0251 (7)	0.0319 (7)	−0.0107 (6)	−0.0055 (6)	−0.0070 (6)
C6	0.0360 (8)	0.0231 (7)	0.0281 (7)	−0.0092 (6)	−0.0046 (6)	−0.0052 (5)
C7	0.0396 (8)	0.0241 (7)	0.0292 (7)	−0.0109 (6)	−0.0097 (6)	−0.0046 (5)
C8	0.0458 (10)	0.0310 (8)	0.0399 (9)	−0.0036 (7)	−0.0058 (8)	−0.0069 (7)
C9	0.0523 (12)	0.0321 (9)	0.0515 (12)	−0.0005 (8)	−0.0151 (9)	0.0004 (8)
C10	0.0546 (12)	0.0396 (10)	0.0379 (9)	−0.0120 (9)	−0.0167 (9)	0.0073 (7)
C11	0.0472 (10)	0.0395 (9)	0.0291 (8)	−0.0110 (8)	−0.0084 (7)	−0.0014 (7)
C12	0.0519 (12)	0.0612 (13)	0.0353 (9)	−0.0152 (10)	−0.0035 (8)	−0.0081 (9)
C13	0.0545 (16)	0.121 (3)	0.0676 (18)	−0.0295 (18)	0.0021 (13)	0.0081 (17)
C14	0.0539 (11)	0.0412 (9)	0.0349 (9)	−0.0148 (8)	−0.0078 (8)	−0.0149 (7)
C15	0.107 (2)	0.0603 (14)	0.0537 (13)	−0.0356 (15)	−0.0343 (14)	−0.0118 (11)

Geometric parameters (Å, º) top

Zn1—O2	2.1369 (17)	C3—H3	0.9300
Zn1—O3	2.289 (2)	C3—C4	1.393 (3)
Zn1—O4	2.0513 (14)	C4—H4	0.9300
Zn1—N1	2.1944 (16)	C4—C5	1.377 (3)
Zn1—N2	2.1702 (14)	C5—C6	1.474 (2)
Zn1—N3ⁱ	2.1921 (14)	C6—C7	1.490 (2)
Zn1—C12	2.538 (2)	C7—C8	1.383 (2)
O1—N2	1.3581 (18)	C8—H8	0.9300
O1—H1	1.11 (4)	C8—C9	1.384 (3)
O2—C12	1.240 (3)	C9—H9	0.9300
O3—C12	1.233 (3)	C9—C10	1.375 (3)
O4—C14	1.251 (2)	C10—H10	0.9300
O5—C14	1.238 (2)	C10—C11	1.374 (3)
O5—H1	1.32 (4)	C11—H11	0.9300
N1—C1	1.339 (2)	C12—C13	1.516 (4)
N1—C5	1.349 (2)	C13—H13A	0.9600
N2—C6	1.279 (2)	C13—H13B	0.9600
N3—C7	1.343 (2)	C13—H13C	0.9600
N3—C11	1.346 (2)	C14—C15	1.498 (3)
C1—H1A	0.9300	C15—H15A	0.9600
C1—C2	1.377 (3)	C15—H15B	0.9600
C2—H2	0.9300	C15—H15C	0.9600
C2—C3	1.368 (3)

O2—Zn1—O3	58.16 (6)	C5—C4—C3	118.68 (18)
O2—Zn1—N1	92.26 (6)	C5—C4—H4	120.7
O2—Zn1—N2	146.35 (6)	N1—C5—C4	122.62 (15)
O2—Zn1—N3ⁱ	89.78 (6)	N1—C5—C6	114.95 (14)
O2—Zn1—C12	29.18 (7)	C4—C5—C6	122.42 (15)
O3—Zn1—C12	29.01 (7)	N2—C6—C5	115.96 (14)
O4—Zn1—O2	99.02 (7)	N2—C6—C7	122.71 (14)
O4—Zn1—O3	98.14 (7)	C5—C6—C7	121.32 (14)
O4—Zn1—N1	168.00 (6)	N3—C7—C6	116.84 (14)
O4—Zn1—N2	98.84 (6)	N3—C7—C8	122.22 (15)
O4—Zn1—N3ⁱ	88.29 (6)	C8—C7—C6	120.94 (16)
O4—Zn1—C12	100.79 (7)	C7—C8—H8	120.4
N1—Zn1—O3	91.27 (7)	C7—C8—C9	119.26 (18)
N1—Zn1—C12	91.05 (7)	C9—C8—H8	120.4
N2—Zn1—O3	91.18 (6)	C8—C9—H9	120.6
N2—Zn1—N1	73.40 (5)	C10—C9—C8	118.83 (18)
N2—Zn1—N3ⁱ	119.03 (6)	C10—C9—H9	120.6
N2—Zn1—C12	118.85 (7)	C9—C10—H10	120.6
N3ⁱ—Zn1—O3	147.87 (6)	C11—C10—C9	118.74 (17)
N3ⁱ—Zn1—N1	87.66 (6)	C11—C10—H10	120.6
N3ⁱ—Zn1—C12	118.87 (6)	N3—C11—C10	123.36 (18)
N2—O1—H1	107.4 (19)	N3—C11—H11	118.3
C12—O2—Zn1	93.65 (15)	C10—C11—H11	118.3
C12—O3—Zn1	86.75 (16)	O2—C12—Zn1	57.18 (12)
C14—O4—Zn1	134.88 (14)	O2—C12—C13	118.1 (2)
C14—O5—H1	120.5 (16)	O3—C12—Zn1	64.23 (14)
C1—N1—Zn1	125.79 (13)	O3—C12—O2	121.3 (2)
C1—N1—C5	117.95 (16)	O3—C12—C13	120.6 (2)
C5—N1—Zn1	116.13 (11)	C13—C12—Zn1	173.8 (2)
O1—N2—Zn1	125.25 (11)	C12—C13—H13A	109.5
C6—N2—Zn1	119.18 (11)	C12—C13—H13B	109.5
C6—N2—O1	115.40 (13)	C12—C13—H13C	109.5
C7—N3—Zn1ⁱ	127.73 (11)	H13A—C13—H13B	109.5
C7—N3—C11	117.57 (15)	H13A—C13—H13C	109.5
C11—N3—Zn1ⁱ	113.67 (12)	H13B—C13—H13C	109.5
N1—C1—H1A	118.9	O4—C14—C15	119.21 (19)
N1—C1—C2	122.28 (18)	O5—C14—O4	125.11 (18)
C2—C1—H1A	118.9	O5—C14—C15	115.68 (19)
C1—C2—H2	120.1	C14—C15—H15A	109.5
C3—C2—C1	119.88 (18)	C14—C15—H15B	109.5
C3—C2—H2	120.1	C14—C15—H15C	109.5
C2—C3—H3	120.7	H15A—C15—H15B	109.5
C2—C3—C4	118.55 (19)	H15A—C15—H15C	109.5
C4—C3—H3	120.7	H15B—C15—H15C	109.5
C3—C4—H4	120.7

Zn1—O2—C12—O3	−3.7 (3)	N2—C6—C7—C8	−64.7 (3)
Zn1—O2—C12—C13	175.4 (2)	N3—C7—C8—C9	1.3 (3)
Zn1—O3—C12—O2	3.4 (3)	C1—N1—C5—C4	2.3 (3)
Zn1—O3—C12—C13	−175.6 (3)	C1—N1—C5—C6	−178.61 (17)
Zn1—O4—C14—O5	−10.1 (4)	C1—C2—C3—C4	1.0 (4)
Zn1—O4—C14—C15	170.56 (18)	C2—C3—C4—C5	0.2 (3)
Zn1—N1—C1—C2	174.66 (17)	C3—C4—C5—N1	−2.0 (3)
Zn1—N1—C5—C4	−173.72 (14)	C3—C4—C5—C6	179.04 (19)
Zn1—N1—C5—C6	5.3 (2)	C4—C5—C6—N2	171.92 (17)
Zn1—N2—C6—C5	5.5 (2)	C4—C5—C6—C7	−7.5 (3)
Zn1—N2—C6—C7	−175.07 (12)	C5—N1—C1—C2	−1.0 (3)
Zn1ⁱ—N3—C7—C6	−14.1 (2)	C5—C6—C7—N3	−65.3 (2)
Zn1ⁱ—N3—C7—C8	165.91 (14)	C5—C6—C7—C8	114.7 (2)
Zn1ⁱ—N3—C11—C10	−168.65 (17)	C6—C7—C8—C9	−178.66 (19)
O1—N2—C6—C5	−179.02 (15)	C7—N3—C11—C10	0.6 (3)
O1—N2—C6—C7	0.4 (3)	C7—C8—C9—C10	0.1 (3)
N1—C1—C2—C3	−0.7 (4)	C8—C9—C10—C11	−1.1 (4)
N1—C5—C6—N2	−7.1 (2)	C9—C10—C11—N3	0.7 (3)
N1—C5—C6—C7	173.44 (16)	C11—N3—C7—C6	178.31 (16)
N2—C6—C7—N3	115.34 (19)	C11—N3—C7—C8	−1.6 (3)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O5	1.11 (4)	1.32 (4)	2.428 (2)	176 (3)
C2—H2···O1ⁱⁱ	0.93	2.34	3.245 (2)	164
C3—H3···O3ⁱⁱⁱ	0.93	2.58	3.293 (3)	134
C9—H9···03^iv	0.93	2.59	3.361 (3)	141
C11—H11···O2ⁱ	0.93	2.38	2.941 (3)	119

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

Acknowledgements

The authors would like to thank CSU-AAUP for research funding.

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