Synthesis, crystal structure and Hirshfeld surface analysis of a polymeric bis­muthate(III) halide complex, (C6H6N3)2[BiCl5]·2H2O

Boukoum, C.; Aloui, Z.; Ferretti, V.; Abid, S.

doi:10.1107/S2056989017015134

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ISSN: 2056-9890

Volume 73| Part 11| November 2017| Pages 1759-1763

https://doi.org/10.1107/S2056989017015134

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Synthesis, crystal structure and Hirshfeld surface analysis of a polymeric bismuthate(III) halide complex, (C₆H₆N₃)₂[BiCl₅]·2H₂O

Chaima Boukoum,^a ^* Zouhaier Aloui,^a Valeria Ferretti ^b and Sonia Abid ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia, and ^bDepartment of Chemical and Pharmaceutical Sciences, Centre for Structural, Diffractometry, University of Ferrara, Via L. Borsari 46, I-44121 Ferrara, Italy
^*Correspondence e-mail: ch.boukoum@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 8 October 2017; accepted 17 October 2017; online 24 October 2017)

The synthesis and the crystal structure of a new halide-bridged polymer, namely catena-poly[bis(1,2,3-benzotriazolium) [[tetrachloridobismuth(III)]-μ-chlorido] dihydrate], {(C₆H₆N₃)₂[BiCl₅]·2H₂O}_n are reported. The structure comprises polyanionic zigzag chains of formula [(BiCl₅)²⁻]_n running along the c-axis direction. The 1,2,3-benzotriazolium cations are linked between these polymer chains, via the water molecules, giving rise to left- and right-handed helical chains. Hirshfeld surface analysis and fingerprint plots were used to decode the intermolecular interactions in the crystal network and determine the contribution of the component units for the construction of the three-dimensional architecture.

Keywords: crystal structure; halogenobismuthates; benzotriazole; Hirshfeld surface analysis.

CCDC reference: 1580458

1. Chemical context

Bismuth–halide complexes are of contemporary interest because of their structural diversity and numerous promising physical properties such as dielectric, ferroelectric, ferroelastic, non-linear optical and thermochromism (Bator et al., 1997 ; Bednarska-Bolek et al., 2000 ; Sobczyk et al., 1997 ; Bator et al., 1998 ). Generally, in these compounds, the BiX₆ octahedra may join to form discrete (i.e. mononuclear) or extended (i.e. polynuclear) inorganic networks of corner-, edge-, or face-sharing octahedra, leading to an extensive family of bismuth halogenoanions (Jakubas, 1986 ; Jakubas et al., 1988 , 1995 ). A variety of organic cations, ring shaped or linear, have a strong impact on the arrangements of BiX₆ octahedra and the formation of hydrogen bonds (Dammak et al., 2015 ; Elfaleh & Kamoun, 2014 ). This class of compounds has also attracted much attention in the field of crystal engineering over the last decade on account of their capability for the creation of extended architectures via intermolecular non-covalent binding interactions. (i.e. hydrogen bonding, ionic and π–π stacking interactions; Belter & Fronczek, 2013 ; Thirunavukkarasu et al., 2013 ; Aloui et al., 2015 ).

As part of our studies in this area, we chose benzotriazole, which is an aromatic heterocyclic base with three protonatable nitrogen atoms, as the organic cation.

2. Structural commentary

The single-crystal X-ray diffraction analysis shows that the title compound [C₆H₆N₃]₂[BiCl₅]·2H₂O, (I), crystallizes in the non-centrosymmetric space group Cmc2₁ and the asymmetric unit comprises one Bi³⁺ cation, four chlorine atoms, one water molecule and one benzotriazolium cation (Fig. 1). The bismuth atom is six-coordinated by four distinct chlorine atoms (Cl1, Cl2, Cl3, Cl4). The Bi—Cl bond lengths (Table 1) vary from 2.545 (3) to 2.674 (4) Å (ΔBi—Cl = 0.129 Å) and 2.757 (4) to 2.856 (4) Å (ΔBi—Cl = 0.099 Å) for non-bridging and bridging Cl atoms, respectively, which are comparable with values found in {(C₂H₇N₄O)₂[BiCl₅]_n (Ferjani et al., 2012 ) and [NH₃(CH₂)₆NH₃]BiCl₅ (Ouasri et al., 2013 ). The Cl—Bi—Cl bond angles in (I) range from 85.93 (17) to 91.88 (13)° (ΔCl—Bi—Cl =5.95°) and are less distorted than those observed in [NH₃(CH₂)₆NH₃]BiCl₅ and [H₂mdap][BiCl₅] (Ouasri et al., 2013; Wang et al., 2017 ).

Table 1
Selected bond lengths (Å)

Bi1—Cl1	2.669 (3)	Bi1—Cl4ⁱ	2.757 (4)
Bi1—Cl2	2.545 (3)	Bi1—Cl4	2.856 (4)
Bi1—Cl3	2.674 (4)
Symmetry code: (i) $[-x+1, -y+1, z-{\script{1\over 2}}]$ .

Figure 1
The asymmetric unit of (I)

showing 50% displacement ellipsoids.

In the extended structure of (I), adjacent BiCl₆ octahedra are connected through Cl4 and Cl4ⁱⁱⁱ so as to form [(BiCl₅)²⁻]_n polyanionic zigzag chains propagating along the c-axis direction, with the shortest intrachain Bi⋯Bi distance of 5.508 (1) Å and a Cl4—Bi—Cl4ⁱⁱ angle of 89.61 (3)° (Fig. 2) The overall negative charges of the resulting polymers are counter-balanced by the protonated 1,2,3-benzotriazolium cations (Fig. 2b). As usual, this aromatic amine is protonated at the N3 atom and the C—C, N—N and C—N bond lengths vary from 1.358 (18) to 1.402 (15), 1.293 (15) to 1.308 (15) Å and 1.364 (16) to 1.370 (15) Å, respectively, which agree well with those observed in bis(1,2,3-benzotriazolium) sulfate dihydrate (Randolph et al., 2013) and benzotriazolium picrate (Zeng et al., 2011 ).

Figure 2
(a) View of the [(BiCl₅)²⁻]_n polyanionic zigzag chains in (I)

along the c-axis direction. (b) Projection along the c axis of the structure of (I)

3. Supramolecular features

The heterocyclic cations alternately bridge the water molecules (O1W) via N—H⋯O hydrogen bonds, forming (benzo-OW)_n helical chains in a right- and left–handed sequence extending along the c-axis direction (Table 2, Fig. 2). The phenyl rings of adjacent chains are alternately stacked in a parallel-displaced face-to-face arrangement (Fig. 3), with centroid–centroid distances of 3.8675 (1) Å and an inter-planar spacing of 1.13 Å. The anionic and cationic chains are further assembled into a three-dimensional supramolecular framework through N—H⋯O, O—H⋯Cl and C—H⋯Cl hydrogen bonds (Table 2, Fig. 3).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1W	0.86	2.08	2.891 (17)	157
N3—H3A⋯O1Wⁱⁱ	0.86	2.00 (2)	2.767 (18)	148
O1W—H11⋯Cl4ⁱⁱⁱ	0.89 (11)	2.47 (11)	3.306 (13)	157 (9)
O1W—H22⋯Cl3	0.90 (12)	2.38 (12)	3.268 (14)	169 (11)
C5—H5⋯Cl1^iv	0.93	2.73	3.603 (14)	157
Symmetry codes: (ii) $[-x+{\script{3\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, -y+1, z+{\script{1\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+1]$ .

Figure 3
View of the infinite helical hydrogen-bonded chain in (I)

4. Hirshfeld surface analysis

The Hirshfeld surface (Wolff et al., 2012 ) mapped with a d_norm function for the asymmetric unit for the title compounds clearly shows the red spots derived from H⋯O and H⋯Cl/Cl⋯H contacts (Fig. 4). The two-dimensional fingerprint plot shows that the H⋯Cl/Cl⋯H contacts associated with O—H⋯Cl hydrogen bonding appear to be the major contributor in the crystal packing (55.8%): these contacts are represented as regions in the top left (d_e > d_i, Cl⋯H) and bottom right (d_e < d_i, H⋯Cl) of the related plots in Fig. 5. Interactions of the type H⋯H appear in the middle of the scattered points in the fingerprint maps; they comprise 10.9% of the entire surface. The decomposition of the fingerprint plot shows that N⋯H/H⋯N, C⋯H/H⋯C, O⋯H/H⋯O and N⋯Cl/Cl⋯N contacts have percentage contributions of 7.8%, 6.5%, 4.5% and 4.3% respectively, of the total Hirshfeld surface. The C⋯C contacts associated with π–π interactions amount to 3.4% of the surface: their presence is indicated by the appearance of red and blue triangles on the shape-indexed surfaces in Fig. 6. The Cl⋯Bi/Bi⋯Cl (3%) interactions are represented as points in the top area. The Cl⋯Cl, C⋯Cl/Cl⋯C, C⋯N, and N⋯N interactions are in the middle of the fingerprint plots, and comprise a very small contribution of 1.3%, 1.2%, 0.9% and 0.4%, respectively.

Figure 4
Hirshfeld surface mapped over d_norm of (I)

Figure 5
Two-dimensional fingerprint plots for (I)

showing contributions from different contacts.

Figure 6
Hirshfeld surface mapped over the shape index for (I)

highlighting the regions involved in π-π stacking interactions.

The intermolecular interactions were further evaluated by using the enrichment ratio (ER; Jelsch et al., 2014 ). The largest contribution to the Hirshfeld surface is from H⋯Cl/Cl⋯H contacts associated with O—H⋯Cl hydrogen bonds and their ER value is 1.73. The H⋯H contacts are the second largest contributor, but they display an enrichment ratio significantly below unity (ER_HH = 0.47). The formation of extensive π–π interactions is reflected in the relatively high ER_CC of 3.94.

5. Synthesis and crystallization

The title compound was prepared by dropwise addition of an ethanolic solution of 1H-benzotriazole (0.061 g, 0.5 mmol) to 1 mmol of a bismuth nitrate solution [Bi(NO₃)₃·5H₂O], dissolved in 0.05 mL of a concentrated HCl aqueous solution. The resulting aqueous solution was stirred for 30 min. and kept at room temperature for crystallization. After two week of slow evaporation, colourless single crystals of (I) (yield = 75%) were formed in the solution. Analysis observed (calculated) for [C₆H₆N₃]₂[BiCl₅]·2H₂O (%): C 21.6 (21.0), H 2.66 (2.41), N 34.6 (33.8).

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The N-bound and C-bound hydrogen atoms were positioned geometrically and treated as riding: N—H = 0.86 Å and C—H = 0.93 Å with U_iso(H) = 1.2U_eq(N,C). The O—H and H⋯H separations in the water molecule were restrained using a DFIX model to be 0.90 and 1.46 Å, respectively, and refined with U_iso(H) = 1.5U_eq(O).

Table 3
Experimental details

Crystal data
Chemical formula	(C₆H₆N₃)₂[BiCl₅]·2H₂O
M_r	662.54
Crystal system, space group	Orthorhombic, Cmc2₁
Temperature (K)	293
a, b, c (Å)	19.4627 (4), 13.8181 (4), 7.7343 (2)
V (Å³)	2080.04 (9)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	9.14
Crystal size (mm)	0.55 × 0.34 × 0.23

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	Multi-scan (SORTAV; Blessing, 1995 )
T_min, T_max	0.011, 0.053
No. of measured, independent and observed [I > 2σ(I)] reflections	6050, 1670, 1643
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.581

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.096, 1.11
No. of reflections	1670
No. of parameters	131
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.68, −0.76
Absolute structure	Flack (1983 ), 731 Friedel pairs
Absolute structure parameter	−0.036 (14)
Computer programs: Kappa CCD server software (Nonius, 1997 ), DENZO-SMN (Otwinowski & Minor, 1997 ), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008 ), ORTEPIII (Burnett & Johnson, 1996 ), and WinGX (Farrugia, 2012 ).

Supporting information

CCDC reference: 1580458

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2056989017015134/hb7714sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017015134/hb7714Isup2.hkl

checkCIF report

Computing details top

Data collection: Kappa CCD server software (Nonius, 1997); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and WinGX (Farrugia, 2012).

catena-Poly[bis(1,2,3-benzotriazolium) [[tetrachloridobismuth(III)]-µ-chlorido] dihydrate] top

Crystal data top

(C₆H₆N₃)₂[BiCl₅]·2H₂O	F(000) = 1256
M_r = 662.54	D_x = 2.116 Mg m⁻³
Orthorhombic, Cmc2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c -2	Cell parameters from 8027 reflections
a = 19.4627 (4) Å	θ = 4.4–7.3°
b = 13.8181 (4) Å	µ = 9.14 mm⁻¹
c = 7.7343 (2) Å	T = 293 K
V = 2080.04 (9) Å³	Rod, colourless
Z = 4	0.55 × 0.34 × 0.23 mm

Data collection top

Nonius KappaCCD diffractometer	1670 independent reflections
Radiation source: fine-focus sealed tube	1643 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.067
f scans and w scans	θ_max = 24.4°, θ_min = 4.4°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −22→22
T_min = 0.011, T_max = 0.053	k = −16→16
6050 measured reflections	l = −8→8

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.038	w = 1/[σ²(F_o²) + (0.0704P)² + 2.8002P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.096	(Δ/σ)_max = 0.038
S = 1.11	Δρ_max = 1.68 e Å⁻³
1670 reflections	Δρ_min = −0.76 e Å⁻³
131 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
4 restraints	Extinction coefficient: 0.0028 (4)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 731 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.036 (14)

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. 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 > 2sigma(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
Bi1	0.5000	0.35812 (2)	0.08277 (6)	0.0310 (2)
Cl1	0.36329 (14)	0.3716 (2)	0.0695 (12)	0.0685 (10)
Cl2	0.5000	0.2105 (2)	−0.1139 (6)	0.0458 (7)
Cl3	0.5000	0.2501 (3)	0.3697 (5)	0.0500 (8)
Cl4	0.5000	0.5302 (3)	0.2874 (5)	0.0652 (10)
O1W	0.6246 (4)	0.3531 (5)	0.585 (3)	0.0570 (18)
C1	0.6621 (5)	0.0963 (7)	0.7492 (14)	0.042 (2)
C2	0.6058 (5)	0.0522 (8)	0.6684 (15)	0.049 (2)
H2C	0.5704	0.0873	0.6175	0.058*
C3	0.6071 (6)	−0.0470 (8)	0.6707 (16)	0.054 (3)
H3	0.5705	−0.0804	0.6215	0.065*
C4	0.6607 (6)	−0.1001 (8)	0.7433 (16)	0.056 (2)
H4	0.6590	−0.1673	0.7390	0.067*
C5	0.7154 (7)	−0.0568 (8)	0.8201 (15)	0.047 (3)
H5	0.7511	−0.0926	0.8684	0.057*
C6	0.7153 (6)	0.0439 (9)	0.8229 (14)	0.040 (2)
N3	0.7585 (5)	0.1125 (8)	0.8909 (15)	0.050 (2)
H3A	0.7954	0.0992	0.9469	0.060*
N1	0.6790 (5)	0.1908 (7)	0.7770 (15)	0.058 (2)
H1	0.6545	0.2390	0.7434	0.070*
N2	0.7371 (5)	0.1995 (8)	0.8609 (16)	0.061 (3)
H11	0.600 (5)	0.400 (8)	0.638 (18)	0.091*
H22	0.595 (5)	0.320 (10)	0.520 (18)	0.091*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Bi1	0.0321 (3)	0.0286 (3)	0.0323 (3)	0.000	0.000	−0.0007 (2)
Cl1	0.0362 (11)	0.0924 (19)	0.077 (3)	0.0003 (11)	0.008 (2)	−0.013 (2)
Cl2	0.0575 (19)	0.0308 (16)	0.0490 (17)	0.000	0.000	−0.0089 (14)
Cl3	0.0605 (19)	0.0469 (19)	0.0427 (16)	0.000	0.000	0.0107 (16)
Cl4	0.088 (3)	0.053 (2)	0.054 (2)	0.000	0.000	−0.0215 (16)
O1W	0.042 (3)	0.060 (5)	0.069 (5)	0.002 (2)	0.002 (10)	−0.010 (5)
C1	0.041 (5)	0.033 (5)	0.051 (5)	0.001 (4)	0.009 (4)	−0.002 (4)
C2	0.047 (5)	0.050 (6)	0.049 (5)	0.008 (4)	0.001 (4)	−0.002 (4)
C3	0.048 (5)	0.056 (7)	0.059 (6)	−0.008 (5)	−0.001 (5)	−0.011 (5)
C4	0.064 (6)	0.042 (6)	0.062 (6)	−0.004 (5)	0.016 (5)	−0.005 (5)
C5	0.053 (7)	0.042 (6)	0.047 (6)	0.011 (5)	0.002 (5)	0.001 (5)
C6	0.032 (5)	0.046 (5)	0.040 (5)	0.004 (4)	0.002 (4)	−0.007 (5)
N3	0.044 (5)	0.053 (6)	0.053 (6)	−0.002 (5)	0.005 (4)	−0.006 (4)
N1	0.052 (5)	0.037 (5)	0.085 (7)	−0.001 (4)	0.011 (5)	−0.005 (5)
N2	0.053 (6)	0.050 (6)	0.080 (7)	−0.016 (5)	0.010 (5)	−0.018 (5)

Geometric parameters (Å, º) top

Bi1—Cl1	2.669 (3)	C2—H2C	0.9300
Bi1—Cl1ⁱ	2.669 (3)	C3—C4	1.394 (17)
Bi1—Cl2	2.545 (3)	C3—H3	0.9300
Bi1—Cl3	2.674 (4)	C4—C5	1.358 (18)
Bi1—Cl4ⁱⁱ	2.757 (4)	C4—H4	0.9300
Bi1—Cl4	2.856 (4)	C5—C6	1.392 (13)
Cl4—Bi1ⁱⁱⁱ	2.757 (4)	C5—H5	0.9300
O1W—H11	0.90 (2)	C6—N3	1.370 (15)
O1W—H22	0.90 (2)	N3—N2	1.293 (15)
C1—N1	1.364 (16)	N3—H3A	0.8600
C1—C6	1.387 (16)	N1—N2	1.308 (15)
C1—C2	1.402 (15)	N1—H1	0.8600
C2—C3	1.371 (16)

Cl2—Bi1—Cl1	91.88 (13)	C3—C2—H2C	122.8
Cl2—Bi1—Cl1ⁱ	91.88 (13)	C1—C2—H2C	122.8
Cl1—Bi1—Cl1ⁱ	170.9 (2)	C2—C3—C4	123.0 (10)
Cl2—Bi1—Cl3	92.80 (16)	C2—C3—H3	118.5
Cl1—Bi1—Cl3	94.06 (17)	C4—C3—H3	118.5
Cl1ⁱ—Bi1—Cl3	94.06 (17)	C5—C4—C3	122.1 (10)
Cl2—Bi1—Cl4ⁱⁱ	87.32 (14)	C5—C4—H4	118.9
Cl1—Bi1—Cl4ⁱⁱ	85.93 (17)	C3—C4—H4	118.9
Cl1ⁱ—Bi1—Cl4ⁱⁱ	85.93 (17)	C4—C5—C6	116.5 (12)
Cl3—Bi1—Cl4ⁱⁱ	179.88 (13)	C4—C5—H5	121.8
Cl2—Bi1—Cl4	176.93 (13)	C6—C5—H5	121.8
Cl1—Bi1—Cl4	87.90 (13)	N3—C6—C1	104.7 (10)
Cl1ⁱ—Bi1—Cl4	87.90 (13)	N3—C6—C5	134.1 (13)
Cl3—Bi1—Cl4	90.27 (13)	C1—C6—C5	121.1 (13)
Cl4ⁱⁱ—Bi1—Cl4	89.61 (3)	N2—N3—C6	112.1 (10)
Bi1ⁱⁱⁱ—Cl4—Bi1	157.68 (19)	N2—N3—H3A	123.9
H11—O1W—H22	106 (3)	C6—N3—H3A	123.9
N1—C1—C6	104.8 (10)	N2—N1—C1	112.0 (10)
N1—C1—C2	132.5 (10)	N2—N1—H1	124.0
C6—C1—C2	122.7 (10)	C1—N1—H1	124.0
C3—C2—C1	114.5 (10)	N3—N2—N1	106.4 (9)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1W	0.86	2.08	2.891 (17)	157
N3—H3A···O1W^iv	0.86	2.00 (2)	2.767 (18)	148
O1W—H11···Cl4ⁱⁱⁱ	0.89 (11)	2.47 (11)	3.306 (13)	157 (9)
O1W—H22···Cl3	0.90 (12)	2.38 (12)	3.268 (14)	169 (11)
C5—H5···Cl1^v	0.93	2.73	3.603 (14)	157

Symmetry codes: (iii) −x+1, −y+1, z+1/2; (iv) −x+3/2, −y+1/2, z+1/2; (v) x+1/2, y−1/2, z+1.

Acknowledgements

This work was supported by the Tunisian Ministry of High Education Scientific Research.

References

Aloui, Z., Ferretti, V., Abid, S., Lefebvre, F., Rzaigui, M. & Nasr, C. B. (2015). J. Mol. Struct. 1097, 166–170. CSD CrossRef CAS
Bator, G., Baran, J., Jakubas, R. & Sobczyk, L. (1998). J. Mol. Struct. 450, 89–100. Web of Science CrossRef CAS
Bator, G., Provoost, R., Silverans, R. E. & Zeegers-Huyskens, Th. (1997). J. Mol. Struct. 435, 1–10. CrossRef CAS
Bednarska-Bolek, B., Zaleski, J., Bator, G. & Jakubas, R. (2000). J. Phys. Chem. Solids, 61, 1249–1261. CAS
Belter, R. K. & Fronczek, F. R. (2013). Acta Cryst. E69, o606–o607. CSD CrossRef IUCr Journals
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
Dammak, H., Feki, H., Boughzala, H. & Abid, Y. (2015). Spectrochim. Acta A Mol. Biomol. Spectrosc. 137, 1235–1243. CSD CrossRef CAS PubMed
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals
Elfaleh, N. & Kamoun, S. (2014). J. Mol. Struct. 1075, 479–485. CSD CrossRef CAS
Ferjani, H., Boughzala, H. & Driss, A. (2012). Acta Cryst. E68, m615. CSD CrossRef IUCr Journals
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals
Jakubas, R. (1986). Solid State Commun. 60, 389–391. CSD CrossRef CAS Web of Science
Jakubas, R., Bator, G. & Mróz, J. (1995). Acta Phys. Pol. A, 87, 663–669. CrossRef CAS
Jakubas, R., Krzewska, U., Bator, G. & Sobczyk, L. (1988). Ferroelectrics, 77, 129–135. CrossRef CAS
Jelsch, C., Ejsmont, K. & Huder, L. (2014). IUCrJ, 1, 119–128. Web of Science CrossRef CAS PubMed IUCr Journals
Nonius (1997). KappaCCD Server Software for Windows. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
Ouasri, A., Jeghnou, H., Rhandour, A. & Roussel, P. (2013). J. Solid State Chem. 200, 22–29. CSD CrossRef CAS
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals
Sobczyk, L., Jakubas, R. & Zaleski, J. (1997). Pol. J. Chem. 71, 265–300. CAS
Thirunavukkarasu, A., Silambarasan, A., Chakkaravarthi, G., Mohankumar, R. & Umarani, P. R. (2013). Acta Cryst. E69, o1605. CSD CrossRef IUCr Journals
Wang, Y., Shi, C. & Han, X. (2017). Polyhedron, 133, 132–136. CSD CrossRef CAS
Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). CrystalExplorer. University of Western Australia.
Zeng, B., Li, J. & Wang, G. (2011). Acta Cryst. E67, o1464. Web of Science CSD CrossRef IUCr Journals

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