1-(2,3-Di­methyl­phen­yl)piperazine-1,4-diium tetra­chlorido­cuprate(II)

Ben Mabrouk, S.; Ameur, I.; Abid, S.; Rzaigui, M.

doi:10.1107/S1600536813021454

metal-organic compounds

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ISSN: 2056-9890

Volume 69| Part 9| September 2013| Page m485

doi:10.1107/S1600536813021454

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1-(2,3-Dimethylphenyl)piperazine-1,4-diium tetrachloridocuprate(II)

Safa Ben Mabrouk,^a Iness Ameur,^a Sonia Abid ^a ^* and Mohamed Rzaigui ^a

^aLaboratoire de Chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
^*Correspondence e-mail: sonia.abid@fsb.rnu.tn

(Received 26 June 2013; accepted 1 August 2013; online 10 August 2013)

In the title salt, (C₁₂H₂₀N₂)[CuCl₄], the Cu^II atom occupies a general position in a flattened tetrahedral environment by Cl ligands, characterized by Cl—Cu—Cl angles of 134.04 (3) and 137.18 (4)°. The six-membered piperazinediium ring adopts a chair conformation. The organic cation and inorganic anion interact through N—H⋯Cl and C—H⋯Cl hydrogen bonds, forming a three-dimensional network.

Related literature

For general background to the properties of tetrahalidocuprate(II) compounds, see: Solomon et al. (1992 ); Kim et al. (2001 ); Panja et al. (2005 ); Lee et al. (2004 ); Turnbull et al. (2005 ); Shapiro et al. (2007 ). For general background to the geometry of the tetrahalidocuprate(II) species, see: Halvorson et al. (1990 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

(C₁₂H₂₀N₂)[CuCl₄]
M_r = 397.64
Triclinic, $[P \overline 1]$
a = 7.1986 (15) Å
b = 7.7611 (11) Å
c = 15.635 (4) Å
α = 77.035 (16)°
β = 79.311 (19)°
γ = 81.845 (14)°
V = 831.9 (3) Å³
Z = 2
Ag Kα radiation
λ = 0.56087 Å
μ = 1.01 mm⁻¹
T = 293 K
0.25 × 0.20 × 0.15 mm

Data collection

Nonius MACH-3 diffractometer
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983 ) T_min = 0.786, T_max = 0.863
9228 measured reflections
8079 independent reflections
4600 reflections with I > 2σ(I)
R_int = 0.020
2 standard reflections every 120 min intensity decay: 7%

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.129
S = 1.00
8079 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 0.87 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl3ⁱ	0.91	2.48	3.1610 (18)	132
N2—H2A⋯Cl2ⁱⁱ	0.90	2.35	3.144 (2)	147
N2—H2B⋯Cl1ⁱⁱⁱ	0.90	2.30	3.152 (2)	159
N2—H2B⋯Cl2ⁱⁱⁱ	0.90	2.80	3.271 (2)	114
C2—H2D⋯Cl1ⁱ	0.97	2.74	3.666 (3)	159
C3—H3B⋯Cl1^iv	0.97	2.78	3.585 (2)	141
C4—H4B⋯Cl4ⁱⁱ	0.97	2.66	3.616 (2)	168
C6—H6⋯Cl4ⁱⁱ	0.93	2.71	3.572 (2)	154
C12—H12C⋯Cl3ⁱ	0.96	2.71	3.568 (3)	149
Symmetry codes: (i) x, y+1, z; (ii) x+1, y, z; (iii) -x+1, -y+1, -z; (iv) x+1, y+1, z.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1996 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813021454/ru2053sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813021454/ru2053Isup2.hkl

checkCIF report

Comment top

Cuprates are chemical compounds in which copper forms complex anions where the overall charge is negative. In such complexes, the ligands are generally cyanides, hydroxides or halides. Due to their important properties, the cuprates still constitute a research axis in many laboratories (Solomon et al., 1992; Kim et al., 2001; Lee et al., 2004; Panja et al., 2005; Turnbull et al., 2005; Shapiro et al., 2007). We report here synthesis and crystal structure of a new cuprate, (C₁₂H₂₀N₂)[CuCl₄] (I). Crystal structure of (I) gives another illustration of this type of material. The asymmetric unit within the unit cell is build of one tetrahedral [CuCl₄]^2- anion and one 1-(2,3-dimethylphenyl)piperazine-1,4-diium cation (Fig. 1). The copper(II) anion exhibits a coordination geometry intermediate between tetrahedral and square–planar. However we can tell that the configuration adopted by this anion is a flattened tetrahedral where the two trans bond angles, Cl(1)—Cu—Cl(4) = 137.18 (4)° and Cl(2)—Cu—Cl(3) = 134.04 (3)°, are very near to the minimum of the potential curve describing the angular deformation of isolated [CuCl₄]^2- anion (θ min = 135.95°) (Halvorson et al., 1990). The phenyl ring (C5—C10) of 1-(2,3-dimethylphenyl)piperazine-1,4-diium is planar with an r.m.s. deviation of 0.0111. The 6-membered piperazinium ring adopts a chair conformation, with puckering parameters (Cremer & Pople, 1975) Q_T = 0.581 (2) Å, θ = 5.3 (2)° and ϕ = 328 (3)°. The dihedral angle between the piperazine (N1–N2/C1–C4) ring and the benzene (C5–C10) ring is 65.41 (7) °. In the crystal, neighboring molecules are linked by N—H···Cl and C—H···Cl hydrogen bonds, forming a three-dimensional network (Figure 2).

Related literature top

For general background to the properties of tetrahalidocuprate(II) compounds, see: Solomon et al. (1992); Kim et al. (2001); Panja et al. (2005); Lee et al. (2004); Turnbull et al. (2005); Shapiro et al. (2007). For general background to the geometry of the tetrahalidocuprate(II) species, see: Halvorson et al. (1990). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

To an aqueous solution (10 ml) of HCl (0.2M) was added 1-(2,3-dimethylphenyl)piperazine (0.19 g, 1 mmol). To the obtained solution, a blue aqueous solution (10 ml) of CuCl₂.6H₂O (0.170 g, 1 mmol) was added slowly with stirring. The resulting solution was submitted to a slow evaporation at room temperature until the formation of yellow crystals of the title compound.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The molecular structure of (I) with 50% probability displacement ellipsoids. Dashed lines indicate C—H···Cl.
	Fig. 2. Perspective view of the three-dimensional network of (I), showing the intermolecular hydrogen bonds (dashed solid lines) interactions.

1-(2,3-Dimethylphenyl)piperazine-1,4-diium tetrachloridocuprate(II) top

Crystal data top

(C₁₂H₂₀N₂)[CuCl₄]	Z = 2
M_r = 397.64	F(000) = 406
Triclinic, P1	D_x = 1.588 Mg m⁻³
Hall symbol: -P 1	Ag Kα radiation, λ = 0.56087 Å
a = 7.1986 (15) Å	Cell parameters from 25 reflections
b = 7.7611 (11) Å	θ = 9.0–10.7°
c = 15.635 (4) Å	µ = 1.01 mm⁻¹
α = 77.035 (16)°	T = 293 K
β = 79.311 (19)°	Prism, yellow
γ = 81.845 (14)°	0.25 × 0.20 × 0.15 mm
V = 831.9 (3) Å³

Data collection top

Nonius MACH-3 diffractometer	4600 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.020
Graphite monochromator	θ_max = 28.0°, θ_min = 2.1°
non–profiled ω scans	h = −12→11
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	k = −12→12
T_min = 0.786, T_max = 0.863	l = −26→2
9228 measured reflections	2 standard reflections every 120 min
8079 independent reflections	intensity decay: 7%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0614P)² + 0.0435P] where P = (F_o² + 2F_c²)/3
8079 reflections	(Δ/σ)_max < 0.001
172 parameters	Δρ_max = 0.87 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³
0 constraints

Crystal data top

(C₁₂H₂₀N₂)[CuCl₄]	γ = 81.845 (14)°
M_r = 397.64	V = 831.9 (3) Å³
Triclinic, P1	Z = 2
a = 7.1986 (15) Å	Ag Kα radiation, λ = 0.56087 Å
b = 7.7611 (11) Å	µ = 1.01 mm⁻¹
c = 15.635 (4) Å	T = 293 K
α = 77.035 (16)°	0.25 × 0.20 × 0.15 mm
β = 79.311 (19)°

Data collection top

Nonius MACH-3 diffractometer	4600 reflections with I > 2σ(I)
Absorption correction: part of the refinement model (ΔF) (Walker & Stuart, 1983)	R_int = 0.020
T_min = 0.786, T_max = 0.863	2 standard reflections every 120 min
9228 measured reflections	intensity decay: 7%
8079 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.00	Δρ_max = 0.87 e Å⁻³
8079 reflections	Δρ_min = −0.68 e Å⁻³
172 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
Cu1	0.28980 (4)	0.31174 (4)	0.166012 (19)	0.03259 (8)
Cl3	0.56150 (8)	0.21183 (7)	0.22023 (4)	0.03825 (13)
Cl2	0.20878 (9)	0.53035 (8)	0.05406 (4)	0.04152 (14)
Cl1	0.27357 (11)	0.07141 (8)	0.10849 (5)	0.04717 (16)
Cl4	0.13588 (11)	0.43179 (10)	0.27862 (5)	0.05472 (19)
N1	0.6470 (2)	0.7932 (2)	0.25996 (11)	0.0256 (3)
H1	0.5611	0.8853	0.2411	0.031*
C5	0.6198 (3)	0.7639 (3)	0.35900 (14)	0.0287 (4)
C10	0.4411 (3)	0.8116 (3)	0.40409 (15)	0.0307 (4)
C4	0.8414 (3)	0.8412 (3)	0.21292 (15)	0.0298 (4)
H4A	0.8718	0.9435	0.2317	0.036*
H4B	0.9365	0.7426	0.2283	0.036*
N2	0.7973 (3)	0.7293 (3)	0.08360 (13)	0.0342 (4)
H2A	0.8894	0.6389	0.0928	0.041*
H2B	0.7938	0.7594	0.0248	0.041*
C9	0.4213 (3)	0.7840 (3)	0.49714 (16)	0.0342 (5)
C1	0.6039 (3)	0.6330 (3)	0.23052 (15)	0.0337 (4)
H1A	0.4785	0.6019	0.2598	0.040*
H1B	0.6956	0.5328	0.2479	0.040*
C2	0.6112 (3)	0.6693 (3)	0.13116 (16)	0.0359 (5)
H2C	0.5914	0.5621	0.1135	0.043*
H2D	0.5098	0.7603	0.1146	0.043*
C6	0.7721 (3)	0.6850 (3)	0.40122 (16)	0.0365 (5)
H6	0.8884	0.6514	0.3688	0.044*
C3	0.8434 (3)	0.8834 (3)	0.11406 (15)	0.0337 (4)
H3A	0.7513	0.9847	0.0988	0.040*
H3B	0.9680	0.9148	0.0839	0.040*
C7	0.7467 (4)	0.6570 (4)	0.49343 (17)	0.0436 (6)
H7	0.8462	0.6033	0.5238	0.052*
C8	0.5736 (4)	0.7093 (3)	0.53963 (17)	0.0420 (5)
H8	0.5590	0.6937	0.6012	0.050*
C11	0.2342 (4)	0.8368 (4)	0.55160 (19)	0.0506 (7)
H70	0.2526	0.8319	0.6114	0.076*
H72	0.1441	0.7564	0.5520	0.076*
H71	0.1871	0.9556	0.5260	0.076*
C12	0.2729 (3)	0.8866 (4)	0.35844 (18)	0.0450 (6)
H12A	0.1645	0.9099	0.4019	0.067*
H12B	0.2459	0.8026	0.3269	0.067*
H12C	0.3005	0.9953	0.3173	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.03341 (14)	0.03084 (14)	0.03585 (16)	0.00481 (10)	−0.01015 (11)	−0.01292 (11)
Cl3	0.0377 (3)	0.0295 (2)	0.0513 (3)	0.0060 (2)	−0.0183 (2)	−0.0128 (2)
Cl2	0.0450 (3)	0.0395 (3)	0.0405 (3)	0.0100 (2)	−0.0159 (3)	−0.0105 (2)
Cl1	0.0676 (4)	0.0333 (3)	0.0480 (4)	−0.0068 (3)	−0.0224 (3)	−0.0121 (3)
Cl4	0.0545 (4)	0.0622 (4)	0.0416 (3)	0.0228 (3)	−0.0035 (3)	−0.0199 (3)
N1	0.0264 (8)	0.0238 (7)	0.0260 (8)	0.0000 (6)	−0.0036 (6)	−0.0058 (6)
C5	0.0346 (10)	0.0263 (9)	0.0254 (9)	−0.0014 (7)	−0.0033 (8)	−0.0081 (7)
C10	0.0313 (10)	0.0303 (10)	0.0301 (10)	−0.0023 (8)	−0.0025 (8)	−0.0078 (8)
C4	0.0278 (9)	0.0309 (10)	0.0312 (10)	−0.0033 (7)	−0.0045 (8)	−0.0072 (8)
N2	0.0353 (9)	0.0381 (10)	0.0304 (9)	0.0012 (7)	−0.0043 (8)	−0.0129 (8)
C9	0.0373 (11)	0.0330 (10)	0.0309 (11)	−0.0076 (9)	0.0033 (9)	−0.0082 (9)
C1	0.0394 (11)	0.0300 (10)	0.0345 (11)	−0.0097 (8)	−0.0031 (9)	−0.0109 (9)
C2	0.0376 (11)	0.0412 (12)	0.0325 (11)	−0.0069 (9)	−0.0060 (9)	−0.0130 (9)
C6	0.0361 (11)	0.0398 (12)	0.0335 (11)	0.0076 (9)	−0.0078 (9)	−0.0123 (9)
C3	0.0345 (11)	0.0351 (11)	0.0314 (11)	−0.0086 (9)	−0.0004 (9)	−0.0072 (9)
C7	0.0475 (14)	0.0492 (14)	0.0334 (12)	0.0070 (11)	−0.0133 (11)	−0.0090 (11)
C8	0.0550 (15)	0.0419 (13)	0.0290 (11)	−0.0022 (11)	−0.0065 (10)	−0.0092 (10)
C11	0.0481 (15)	0.0613 (17)	0.0385 (14)	−0.0070 (13)	0.0094 (12)	−0.0145 (13)
C12	0.0295 (11)	0.0605 (16)	0.0396 (13)	−0.0013 (11)	−0.0021 (10)	−0.0040 (12)

Geometric parameters (Å, º) top

Cu1—Cl4	2.2170 (9)	C9—C11	1.510 (3)
Cu1—Cl3	2.2439 (8)	C1—C2	1.508 (3)
Cu1—Cl2	2.2467 (8)	C1—H1A	0.9700
Cu1—Cl1	2.2704 (7)	C1—H1B	0.9700
N1—C5	1.493 (3)	C2—H2C	0.9700
N1—C1	1.507 (3)	C2—H2D	0.9700
N1—C4	1.511 (3)	C6—C7	1.390 (3)
N1—H1	0.9100	C6—H6	0.9300
C5—C6	1.382 (3)	C3—H3A	0.9700
C5—C10	1.391 (3)	C3—H3B	0.9700
C10—C9	1.405 (3)	C7—C8	1.376 (4)
C10—C12	1.499 (3)	C7—H7	0.9300
C4—C3	1.504 (3)	C8—H8	0.9300
C4—H4A	0.9700	C11—H70	0.9600
C4—H4B	0.9700	C11—H72	0.9600
N2—C3	1.481 (3)	C11—H71	0.9600
N2—C2	1.488 (3)	C12—H12A	0.9600
N2—H2A	0.9000	C12—H12B	0.9600
N2—H2B	0.9000	C12—H12C	0.9600
C9—C8	1.377 (4)

Cl4—Cu1—Cl3	97.87 (3)	N1—C1—H1B	109.4
Cl4—Cu1—Cl2	98.37 (3)	C2—C1—H1B	109.4
Cl3—Cu1—Cl2	134.04 (3)	H1A—C1—H1B	108.0
Cl4—Cu1—Cl1	137.18 (4)	N2—C2—C1	111.22 (19)
Cl3—Cu1—Cl1	96.67 (3)	N2—C2—H2C	109.4
Cl2—Cu1—Cl1	99.83 (3)	C1—C2—H2C	109.4
C5—N1—C1	111.00 (16)	N2—C2—H2D	109.4
C5—N1—C4	115.08 (16)	C1—C2—H2D	109.4
C1—N1—C4	108.77 (16)	H2C—C2—H2D	108.0
C5—N1—H1	107.2	C5—C6—C7	118.2 (2)
C1—N1—H1	107.2	C5—C6—H6	120.9
C4—N1—H1	107.2	C7—C6—H6	120.9
C6—C5—C10	123.4 (2)	N2—C3—C4	110.92 (18)
C6—C5—N1	118.13 (19)	N2—C3—H3A	109.5
C10—C5—N1	118.40 (19)	C4—C3—H3A	109.5
C5—C10—C9	116.8 (2)	N2—C3—H3B	109.5
C5—C10—C12	123.3 (2)	C4—C3—H3B	109.5
C9—C10—C12	119.9 (2)	H3A—C3—H3B	108.0
C3—C4—N1	109.47 (17)	C8—C7—C6	119.7 (2)
C3—C4—H4A	109.8	C8—C7—H7	120.1
N1—C4—H4A	109.8	C6—C7—H7	120.1
C3—C4—H4B	109.8	C7—C8—C9	121.7 (2)
N1—C4—H4B	109.8	C7—C8—H8	119.1
H4A—C4—H4B	108.2	C9—C8—H8	119.1
C3—N2—C2	111.79 (17)	C9—C11—H70	109.5
C3—N2—H2A	109.3	C9—C11—H72	109.5
C2—N2—H2A	109.3	H70—C11—H72	109.5
C3—N2—H2B	109.3	C9—C11—H71	109.5
C2—N2—H2B	109.3	H70—C11—H71	109.5
H2A—N2—H2B	107.9	H72—C11—H71	109.5
C8—C9—C10	120.1 (2)	C10—C12—H12A	109.5
C8—C9—C11	119.2 (2)	C10—C12—H12B	109.5
C10—C9—C11	120.6 (2)	H12A—C12—H12B	109.5
N1—C1—C2	111.01 (18)	C10—C12—H12C	109.5
N1—C1—H1A	109.4	H12A—C12—H12C	109.5
C2—C1—H1A	109.4	H12B—C12—H12C	109.5

C1—N1—C5—C6	88.3 (2)	C12—C10—C9—C11	−2.8 (4)
C4—N1—C5—C6	−35.8 (3)	C5—N1—C1—C2	174.05 (18)
C1—N1—C5—C10	−89.5 (2)	C4—N1—C1—C2	−58.4 (2)
C4—N1—C5—C10	146.48 (19)	C3—N2—C2—C1	−53.9 (3)
C6—C5—C10—C9	3.1 (3)	N1—C1—C2—N2	55.3 (3)
N1—C5—C10—C9	−179.34 (19)	C10—C5—C6—C7	−2.1 (4)
C6—C5—C10—C12	−176.0 (2)	N1—C5—C6—C7	−179.7 (2)
N1—C5—C10—C12	1.6 (3)	C2—N2—C3—C4	56.3 (2)
C5—N1—C4—C3	−174.74 (17)	N1—C4—C3—N2	−59.4 (2)
C1—N1—C4—C3	60.0 (2)	C5—C6—C7—C8	−0.5 (4)
C5—C10—C9—C8	−1.4 (3)	C6—C7—C8—C9	2.1 (4)
C12—C10—C9—C8	177.7 (2)	C10—C9—C8—C7	−1.1 (4)
C5—C10—C9—C11	178.2 (2)	C11—C9—C8—C7	179.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl3ⁱ	0.91	2.48	3.1610 (18)	132
N2—H2A···Cl2ⁱⁱ	0.90	2.35	3.144 (2)	147
N2—H2B···Cl1ⁱⁱⁱ	0.90	2.30	3.152 (2)	159
N2—H2B···Cl2ⁱⁱⁱ	0.90	2.80	3.271 (2)	114
C2—H2D···Cl1ⁱ	0.97	2.74	3.666 (3)	159
C3—H3B···Cl1^iv	0.97	2.78	3.585 (2)	141
C4—H4B···Cl4ⁱⁱ	0.97	2.66	3.616 (2)	168
C6—H6···Cl4ⁱⁱ	0.93	2.71	3.572 (2)	154
C12—H12C···Cl3ⁱ	0.96	2.71	3.568 (3)	149

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl3ⁱ	0.91	2.48	3.1610 (18)	131.7
N2—H2A···Cl2ⁱⁱ	0.90	2.35	3.144 (2)	147.0
N2—H2B···Cl1ⁱⁱⁱ	0.90	2.30	3.152 (2)	158.8
N2—H2B···Cl2ⁱⁱⁱ	0.90	2.80	3.271 (2)	113.9
C2—H2D···Cl1ⁱ	0.97	2.74	3.666 (3)	159.4
C3—H3B···Cl1^iv	0.97	2.78	3.585 (2)	140.5
C4—H4B···Cl4ⁱⁱ	0.97	2.66	3.616 (2)	168.0
C6—H6···Cl4ⁱⁱ	0.93	2.71	3.572 (2)	154.2
C12—H12C···Cl3ⁱ	0.96	2.71	3.568 (3)	148.9

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

Acknowledgements

This work was supported by the Tunisian Ministry of HEScR.

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