Crystal structure of bis­[2,5-bis­(pyridin-2-yl)-1,3,4-thia­diazole-κ2N2,N3]bis­(thio­cyanato-κS)copper(II)

Laachir, A.; Bentiss, F.; Guesmi, S.; Saadi, M.; El Ammari, L.

doi:10.1107/S2056989016011713

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ISSN: 2056-9890

Volume 72| Part 8| August 2016| Pages 1176-1178

https://doi.org/10.1107/S2056989016011713

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Crystal structure of bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ²N²,N³]bis(thiocyanato-κS)copper(II)

Abdelhakim Laachir,^a Fouad Bentiss,^b Salaheddine Guesmi,^a ^* Mohamed Saadi ^c and Lahcen El Ammari ^c

^aLaboratoire de Chimie de Coordination et d'Analytique (LCCA), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida, Morocco, ^bLaboratoire de Catalyse et de Corrosion de Matériaux (LCCM), Faculté des Sciences, Université Chouaib Doukkali, BP 20, M-24000 El Jadida, Morocco, and ^cLaboratoire de Chimie du Solide Appliquée, Faculty of Sciences, Mohammed V University in Rabat, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: salaheddine_guesmi@yahoo.fr

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 8 July 2016; accepted 18 July 2016; online 22 July 2016)

The mononuclear title complex, [Cu(SCN)₂(C₁₂H₈N₄S)₂], was obtained by the reaction of 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole and potassium thiocyanate with copper(II) chloride dihydrate. The copper cation lies on an inversion centre and displays an elongated octahedral coordination geometry. The equatorial positions are occupied by the N atoms of two 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole ligands, whereas the axial positions are occupied by the S atoms of two thiocyanate anions. The thiadiazole and the pyridyl rings linked to the metal are approximately coplanar, with a maximum deviation from the mean plane of 0.190 (2) Å. The cohesion of the crystal structure is ensured by weak C—H⋯N hydrogen bonds and π–π interactions between parallel pyridyl rings of neighbouring molecules [centroid-to-centroid distance = 3.663 (2) Å], leading to a three-dimensional network.

Keywords: crystal structure; copper complex; 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole; thiocyanate ligand.

CCDC reference: 1494615

1. Chemical context

The use of compounds containing a 1,3,4-thiadiazole moiety as part of ligand systems has gained considerable attention in recent years (Kadam Sushama et al., 2016 ). Indeed, a 2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole (bptd) and its metal complexes have been extensively studied because of their potential applications in biology (Baghel et al., 2014 ; Ahmed et al., 2015 ; Zine et al., 2016 ), magnetism (Bentiss et al., 2004 ) and coordination chemistry (Bentiss et al., 2002 ). An interesting feature of the metal-ligand chemistry of these compounds is that the complexes can be mononuclear (Bentiss et al., 2011 , 2012 ; Klingele et al., 2010 ; Kaase & Klingele, 2014 ) or binuclear (Laachir et al., 2013 ).

We have recently reported the synthesis and characterization of monomeric complexes of Ni^II and Co^II with bptd in the presence of the pseudohalide azide (Laachir et al., 2015a ,b ). In this context, we report here the synthesis and crystal structure of a new Cu^II complex with bptd and thiocyanate as co-ligands.

2. Structural commentary

The title complex has crystallographically imposed inversion symmetry, the copper atom lying on the Wyckoff special position 2b of the space group P2₁/c. The elongated octahedral coordination polyhedron around the metal cation is provided by four nitrogen atoms of pyridine and thiadiazole rings occupying the equatorial plane and by the sulfur atoms of two thiocyanate anions at the apical positions (Fig. 1). The Cu—N distances are 2.0267 (16) and 2.0463 (15) Å, the Cu—S bond length is 2.8125 (7) Å. A bond-valence-sum calculation (Brown & Altermatt, 1985 ) for Cu gives the expected BVS value of 2.11 valence units. The conformation of the ligand is approximately planar, with a maximum deviation from the least-squares plane of 0.190 (2) Å for atom C12. The dihedral angles formed by the thiadiazole ring with the N1/C2–C6 and N4/C8–C12 pyridine rings are 1.94 (8) and 6.96 (5)°, respectively.

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles. [Symmetry code: (i) −x + 1, −y + 1, −z + 1.]

3. Supramolecular features

In the crystal, the molecules are linked by weak C—H⋯N hydrogen bonds (Table 1) and by π–π stacking interactions between the pyridyl rings of adjacent complex molecules [intercentroid distance = 3.663 (2) Å], forming a three-dimensional network (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N5ⁱ	0.93	2.53	3.353 (3)	147
C6—H6⋯N3ⁱⁱ	0.93	2.35	3.143 (3)	142
C4—H4⋯N4ⁱⁱⁱ	0.93	2.57	3.458 (3)	161
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Crystal packing of the title compound, showing π–π interactions between pyridyl rings (green dashed lines) and intermolecular hydrogen bonds (blue dashed lines).

4. Database survey

The structure of the title compound is similar to that of the related complexes [Co(C₁₂H₈N₄S)₂(N₃)₂] (Laachir et al., 2015b) and [Ni(C₁₂H₈N₄S)₂(N₃)₂] (Laachir et al., 2015a), in which the azide ion is substituted by the thiocyanate group. The CuN₄S₂ octahedron is more distorted than the NiN₆ and CoN₆ octahedra.

5. Synthesis and crystallization

2,5-Bis(pyridin-2-yl)-1,3,4-thiadiazole (bptd) was synthesized as described previously by Lebrini et al. (2005 ). A solution of bptd (24 mg, 0.1 mmol) in CH₃CN (10 mL) was layered onto a solution of CuCl₂·2H₂O (17 mg, 0.1 mmol) and KSCN (20 mg, 0.2 mmol) in CH₃CN/H₂O (1:1 v/v, 10 mL) in a test tube. The solution was left for two months at room temperature to give X-ray quality brown block-shaped crystals. After filtration, the product was washed with cold EtOH and dried under vacuum. Crystals were washed with water and dried under vacuum (yield 60%; m.p. 538 K). Analysis calculated for C₂₆H₁₆N₁₀S₄Cu: C, 47.30; H, 2.44; N, 21.21 S, 19.42. Found: C, 47.06; H, 2.43; N, 21.03; S, 19.56.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were located in a difference Fourier map and treated as riding, with C—H = 0.96 Å, and with U_iso(H) = 1.2 U_eq(C). One outlier (002) was omitted in the last cycles of refinement.

Table 2
Experimental details

Crystal data
Chemical formula	[Cu(SCN)₂(C₁₂H₈N₄S)₂]
M_r	660.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	8.0205 (3), 7.8434 (3), 21.3454 (9)
β (°)	92.565 (2)
V (Å³)	1341.45 (9)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.17
Crystal size (mm)	0.35 × 0.32 × 0.26

Data collection
Diffractometer	Bruker X8 APEX
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.604, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	42199, 4089, 3155
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.714

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.097, 1.04
No. of reflections	4089
No. of parameters	187
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.51
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1494615

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989016011713/rz5192sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016011713/rz5192Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2008) and publCIF (Westrip, 2010).

Bis[2,5-bis(pyridin-2-yl)-1,3,4-thiadiazole-κ²N²,N³]bis(thiocyanato-κS)copper(II) top

Crystal data top

[Cu(NCS)₂(C₁₂H₈N₄S)₂]	D_x = 1.635 Mg m⁻³
M_r = 660.27	Melting point: 538 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.0205 (3) Å	Cell parameters from 4089 reflections
b = 7.8434 (3) Å	θ = 2.5–30.5°
c = 21.3454 (9) Å	µ = 1.17 mm⁻¹
β = 92.565 (2)°	T = 296 K
V = 1341.45 (9) Å³	Block, brown
Z = 2	0.35 × 0.32 × 0.26 mm
F(000) = 670

Data collection top

Bruker X8 APEX diffractometer	4089 independent reflections
Radiation source: fine-focus sealed tube	3155 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.060
φ and ω scans	θ_max = 30.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −11→11
T_min = 0.604, T_max = 0.746	k = −11→11
42199 measured reflections	l = −27→30

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.036	H-atom parameters constrained
wR(F²) = 0.097	w = 1/[σ²(F_o²) + (0.0418P)² + 0.834P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
4089 reflections	Δρ_max = 0.56 e Å⁻³
187 parameters	Δρ_min = −0.51 e Å⁻³

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
C1	0.4345 (2)	0.6803 (2)	0.38733 (8)	0.0240 (4)
C2	0.5958 (2)	0.6037 (2)	0.37724 (8)	0.0240 (4)
C3	0.6786 (3)	0.6181 (3)	0.32209 (9)	0.0327 (4)
H3	0.6314	0.6778	0.2881	0.039*
C4	0.8333 (3)	0.5416 (3)	0.31863 (10)	0.0372 (5)
H4	0.8909	0.5469	0.2818	0.045*
C5	0.9012 (3)	0.4572 (3)	0.37055 (11)	0.0366 (5)
H5	1.0065	0.4079	0.3696	0.044*
C6	0.8102 (3)	0.4473 (3)	0.42395 (10)	0.0320 (4)
H6	0.8563	0.3896	0.4586	0.038*
C7	0.1712 (2)	0.8133 (2)	0.39355 (9)	0.0251 (4)
C8	0.0124 (2)	0.9022 (3)	0.38144 (9)	0.0270 (4)
C9	−0.1027 (3)	0.9212 (3)	0.42773 (10)	0.0322 (4)
H9	−0.0804	0.8796	0.4680	0.039*
C10	−0.2511 (3)	1.0036 (3)	0.41222 (12)	0.0387 (5)
H10	−0.3306	1.0198	0.4421	0.046*
C11	−0.2792 (3)	1.0615 (3)	0.35150 (12)	0.0430 (5)
H11	−0.3782	1.1168	0.3396	0.052*
C12	−0.1570 (3)	1.0356 (3)	0.30870 (12)	0.0439 (6)
H12	−0.1772	1.0747	0.2679	0.053*
C13	0.3302 (3)	0.2765 (3)	0.36867 (13)	0.0423 (5)
N1	0.65894 (19)	0.5170 (2)	0.42789 (7)	0.0246 (3)
N2	0.36607 (19)	0.6566 (2)	0.44138 (7)	0.0258 (3)
N3	0.2129 (2)	0.7323 (2)	0.44510 (7)	0.0282 (3)
N4	−0.0124 (2)	0.9581 (2)	0.32252 (8)	0.0354 (4)
N5	0.3255 (3)	0.3117 (3)	0.31799 (10)	0.0568 (6)
Cu1	0.5000	0.5000	0.5000	0.02713 (10)
S1	0.31614 (6)	0.80256 (7)	0.33603 (2)	0.02941 (12)
S2	0.33021 (9)	0.22277 (9)	0.44310 (3)	0.04809 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0269 (9)	0.0275 (9)	0.0174 (8)	−0.0018 (7)	0.0005 (6)	0.0016 (7)
C2	0.0256 (8)	0.0274 (9)	0.0191 (8)	−0.0026 (7)	0.0017 (6)	−0.0008 (7)
C3	0.0359 (10)	0.0429 (12)	0.0196 (9)	−0.0034 (9)	0.0058 (7)	0.0018 (8)
C4	0.0368 (11)	0.0480 (13)	0.0278 (11)	−0.0035 (9)	0.0142 (8)	−0.0039 (9)
C5	0.0309 (10)	0.0421 (12)	0.0379 (12)	0.0034 (9)	0.0140 (9)	−0.0007 (9)
C6	0.0298 (10)	0.0346 (10)	0.0322 (11)	0.0052 (8)	0.0067 (8)	0.0050 (8)
C7	0.0244 (8)	0.0291 (9)	0.0219 (9)	−0.0009 (7)	0.0004 (6)	0.0005 (7)
C8	0.0257 (9)	0.0294 (9)	0.0256 (9)	−0.0003 (7)	−0.0006 (7)	0.0017 (7)
C9	0.0327 (10)	0.0371 (11)	0.0269 (10)	0.0007 (8)	0.0020 (8)	0.0004 (8)
C10	0.0318 (10)	0.0400 (12)	0.0449 (13)	0.0049 (9)	0.0081 (9)	−0.0054 (10)
C11	0.0314 (11)	0.0419 (12)	0.0554 (15)	0.0082 (9)	−0.0016 (10)	0.0047 (11)
C12	0.0414 (12)	0.0523 (14)	0.0376 (13)	0.0085 (11)	−0.0036 (10)	0.0139 (11)
C13	0.0331 (11)	0.0369 (12)	0.0568 (16)	0.0028 (9)	0.0003 (10)	−0.0137 (11)
N1	0.0247 (7)	0.0278 (8)	0.0217 (8)	0.0002 (6)	0.0047 (6)	0.0015 (6)
N2	0.0246 (7)	0.0311 (8)	0.0216 (8)	0.0017 (6)	0.0016 (6)	0.0026 (6)
N3	0.0267 (8)	0.0346 (9)	0.0236 (8)	0.0046 (7)	0.0035 (6)	0.0034 (7)
N4	0.0319 (9)	0.0440 (10)	0.0304 (9)	0.0065 (8)	0.0022 (7)	0.0108 (8)
N5	0.0803 (17)	0.0623 (15)	0.0260 (10)	0.0160 (13)	−0.0157 (10)	−0.0098 (10)
Cu1	0.02419 (16)	0.0377 (2)	0.02004 (17)	0.00875 (13)	0.00685 (11)	0.00895 (13)
S1	0.0304 (2)	0.0383 (3)	0.0196 (2)	0.0038 (2)	0.00108 (17)	0.00653 (19)
S2	0.0581 (4)	0.0487 (4)	0.0380 (3)	−0.0128 (3)	0.0077 (3)	−0.0015 (3)

Geometric parameters (Å, º) top

C1—N2	1.313 (2)	C10—C11	1.382 (4)
C1—C2	1.452 (3)	C10—H10	0.9300
C1—S1	1.7106 (18)	C11—C12	1.384 (4)
C2—N1	1.356 (2)	C11—H11	0.9300
C2—C3	1.382 (3)	C12—N4	1.331 (3)
C2—S1	2.8397 (19)	C12—H12	0.9300
C3—C4	1.383 (3)	C13—N5	1.115 (3)
C3—H3	0.9300	C13—S2	1.644 (3)
C4—C5	1.382 (3)	N1—Cu1	2.0463 (15)
C4—H4	0.9300	N2—N3	1.370 (2)
C5—C6	1.383 (3)	N2—Cu1	2.0267 (16)
C5—H5	0.9300	N2—S1	2.5392 (16)
C6—N1	1.337 (2)	N3—S1	2.5657 (16)
C6—H6	0.9300	N4—S1	2.9062 (18)
C7—N3	1.301 (2)	N5—S2	2.759 (2)
C7—C8	1.465 (3)	Cu1—N2ⁱ	2.0267 (16)
C7—S1	1.7300 (19)	Cu1—N1ⁱ	2.0463 (15)
C8—N4	1.338 (3)	Cu1—S2ⁱ	2.8124 (7)
C8—C9	1.390 (3)	Cu1—S2	2.8125 (7)
C8—S1	2.774 (2)	S1—S2ⁱⁱ	4.0094 (9)
C9—C10	1.382 (3)	S2—S1ⁱⁱⁱ	4.0094 (9)
C9—H9	0.9300

N2—C1—C2	118.82 (16)	N2—N3—S1	73.37 (9)
N2—C1—S1	113.60 (14)	C12—N4—C8	116.71 (19)
C2—C1—S1	127.58 (14)	C12—N4—S1	172.31 (16)
N1—C2—C3	122.97 (18)	C8—N4—S1	70.92 (11)
N1—C2—C1	113.12 (15)	C13—N5—S2	1.19 (15)
C3—C2—C1	123.91 (18)	N2—Cu1—N2ⁱ	180.0
N1—C2—S1	141.62 (12)	N2—Cu1—N1ⁱ	99.96 (6)
C3—C2—S1	95.40 (13)	N2ⁱ—Cu1—N1ⁱ	80.04 (6)
C1—C2—S1	28.52 (8)	N2—Cu1—N1	80.04 (6)
C2—C3—C4	118.45 (19)	N2ⁱ—Cu1—N1	99.96 (6)
C2—C3—H3	120.8	N1ⁱ—Cu1—N1	180.0
C4—C3—H3	120.8	N2—Cu1—S2ⁱ	91.78 (5)
C5—C4—C3	119.16 (19)	N2ⁱ—Cu1—S2ⁱ	88.22 (5)
C5—C4—H4	120.4	N1ⁱ—Cu1—S2ⁱ	91.80 (5)
C3—C4—H4	120.4	N1—Cu1—S2ⁱ	88.20 (5)
C4—C5—C6	119.0 (2)	N2—Cu1—S2	88.22 (5)
C4—C5—H5	120.5	N2ⁱ—Cu1—S2	91.78 (5)
C6—C5—H5	120.5	N1ⁱ—Cu1—S2	88.20 (5)
N1—C6—C5	122.9 (2)	N1—Cu1—S2	91.80 (5)
N1—C6—H6	118.6	S2ⁱ—Cu1—S2	180.00 (2)
C5—C6—H6	118.6	C1—S1—C7	86.79 (9)
N3—C7—C8	124.76 (17)	C1—S1—N2	28.28 (7)
N3—C7—S1	114.92 (14)	C7—S1—N2	58.51 (7)
C8—C7—S1	120.27 (14)	C1—S1—N3	59.41 (7)
N4—C8—C9	123.86 (18)	C7—S1—N3	27.38 (7)
N4—C8—C7	114.43 (17)	N2—S1—N3	31.13 (5)
C9—C8—C7	121.69 (18)	C1—S1—C8	113.89 (8)
N4—C8—S1	81.95 (12)	C7—S1—C8	27.14 (7)
C9—C8—S1	154.16 (14)	N2—S1—C8	85.63 (5)
C7—C8—S1	32.59 (9)	N3—S1—C8	54.50 (5)
C10—C9—C8	118.2 (2)	C1—S1—C2	23.90 (7)
C10—C9—H9	120.9	C7—S1—C2	110.69 (7)
C8—C9—H9	120.9	N2—S1—C2	52.18 (5)
C9—C10—C11	118.7 (2)	N3—S1—C2	83.31 (5)
C9—C10—H10	120.6	C8—S1—C2	137.77 (6)
C11—C10—H10	120.6	C1—S1—N4	140.66 (7)
C10—C11—C12	118.7 (2)	C7—S1—N4	54.21 (7)
C10—C11—H11	120.6	N2—S1—N4	112.55 (5)
C12—C11—H11	120.6	N3—S1—N4	81.50 (5)
N4—C12—C11	123.8 (2)	C8—S1—N4	27.13 (5)
N4—C12—H12	118.1	C2—S1—N4	164.06 (5)
C11—C12—H12	118.1	C1—S1—S2ⁱⁱ	95.46 (7)
N5—C13—S2	178.0 (3)	C7—S1—S2ⁱⁱ	63.79 (7)
C6—N1—C2	117.53 (16)	N2—S1—S2ⁱⁱ	82.33 (4)
C6—N1—Cu1	128.20 (13)	N3—S1—S2ⁱⁱ	70.21 (4)
C2—N1—Cu1	114.18 (12)	C8—S1—S2ⁱⁱ	64.66 (4)
C1—N2—N3	113.62 (15)	C2—S1—S2ⁱⁱ	105.86 (4)
C1—N2—Cu1	113.43 (13)	N4—S1—S2ⁱⁱ	73.36 (4)
N3—N2—Cu1	132.74 (12)	C13—S2—N5	0.81 (10)
C1—N2—S1	38.12 (9)	C13—S2—Cu1	101.44 (9)
N3—N2—S1	75.50 (9)	N5—S2—Cu1	102.00 (6)
Cu1—N2—S1	151.43 (8)	C13—S2—S1ⁱⁱⁱ	70.19 (8)
C7—N3—N2	111.07 (15)	N5—S2—S1ⁱⁱⁱ	69.96 (5)
C7—N3—S1	37.70 (9)	Cu1—S2—S1ⁱⁱⁱ	151.94 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N5^iv	0.93	2.53	3.353 (3)	147
C6—H6···N3ⁱ	0.93	2.35	3.143 (3)	142
C4—H4···N4^v	0.93	2.57	3.458 (3)	161

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and Chouaib Doukkali University, El Jadida, Morocco, for financial support.

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