Di­chlorido­(5,10,15,20-tetra­phenyl­porphyrinato-κ4N)anti­mony(V) hexa­chlorido­anti­monate(V)

Soury, R.; Belkhiria, M.S.; Giorgi, M.; Nasri, H.

doi:10.1107/S1600536814012653

metal-organic compounds

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ISSN: 2056-9890

Volume 70| Part 7| July 2014| Pages m256-m257

https://doi.org/10.1107/S1600536814012653

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Dichlorido(5,10,15,20-tetraphenylporphyrinato-κ⁴N)antimony(V) hexachloridoantimonate(V)

Raoudha Soury,^a Mohamed Salah Belkhiria,^a ^* Michel Giorgi ^b and Habib Nasri ^a

^aLaboratoire de Physico-Chimie des Matériaux, Université de Monastir, Faculté des Sciences de Monastir, Avenue de l'environnement, 5019 Monastir, Tunisia, and ^bSpectropole, Université d'Aix-Marseille, Faculté des Science, St-Jérôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France
^*Correspondence e-mail: salah_belkiria@yahoo.com

(Received 5 April 2014; accepted 30 May 2014; online 11 June 2014)

The asymmetric unit of the title compound, [Sb(C₄₄H₂₈N₄)Cl₂][SbCl₆], consists of one half of an antimony(V) tetraphenylporphyrin complex cation and one half of an hexachloridoantimonate(V) anion. In the complex cation, the Sb^V atom lies on an inversion center and is octahedrally coordinated by four N atoms from a macrocyclic tetraphenylporphyrinate ligand and two chloride ions. The complex cation has approximately a planar core with a maximum deviation of 0.018 (5) Å from the porphyrin mean plane. The average Sb—N distance is 2.062 (11) Å, while the Sb—Cl distance is 2.355 (1) Å. The Sb^V atom of the anion is also located on an inversion center. The [SbCl₆]⁻ octahedron exhibits rhombic distortion characterized by the Sb—Cl bond lengths [2.311 (3), 2.374 (2) and 2.393 (4) Å]. In the crystal, the cations and anions are linked C—H⋯ Cl hydrogen bonds, forming a layer parallel to (211).

CCDC reference: 1006075

Related literature

For general background and the synthesis, see: Liu et al. (1996 ). For related structures, see: Tsunami et al. (2008 ); Soury et al. (2012 ).

Experimental

Crystal data

[Sb(C₄₄H₂₈N₄)Cl₂][SbCl₆]
M_r = 1139.80
Triclinic, $[P \overline 1]$
a = 10.2044 (4) Å
b = 11.1242 (4) Å
c = 11.3901 (4) Å
α = 70.685 (2)°
β = 83.398 (2)°
γ = 63.050 (3)°
V = 1086.73 (7) Å³
Z = 1
Mo Kα radiation
μ = 1.77 mm⁻¹
T = 223 K
0.2 × 0.16 × 0.12 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.723, T_max = 0.773
19871 measured reflections
4749 independent reflections
4433 reflections with I > 2σ(I)
R_int = 0.124

Refinement

R[F² > 2σ(F²)] = 0.065
wR(F²) = 0.173
S = 1.13
4749 reflections
266 parameters
H-atom parameters constrained
Δρ_max = 2.55 e Å⁻³
Δρ_min = −1.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cl3ⁱ	0.94	2.76	3.490 (8)	135
C8—H8⋯Cl4	0.94	2.74	3.593 (8)	151
C12—H12⋯Cl3ⁱⁱ	0.94	2.69	3.539 (8)	151
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x, y, z-1.

Data collection: COLLECT (Nonius, 2002 ); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1006075

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536814012653/is5356sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814012653/is5356Isup2.hkl

checkCIF report

Comment top

As part of our continuing studies of antimony porphyrin complexes (Soury et al., 2012), we report here the synthesis and crystal structure of the tiltle compound [Sb(tpp)Cl₂][SbCl₆] which appears to be the eleventh X-ray structure of an antimony porphyrin complex in the literature.

The molecular structures of the antimony(V) porphyrin cation [Sb(tpp)Cl₂]⁺ and the hexachloridoantimonate(V) [SbCl₆]^- anion of the title compound are given in Figure 1. The Sb atom of the porphyrin complex lies on an inversion center and at the same time in the porphyrin mean plane (C₂₄N₄). The average Sb—N distance and the Sb—Cl distance values, respectively equal to 2.062 (4) Å and 2.355 (1) Å, agree very well with those reported in literature (Liu et al., 1996; Tsunami et al., 2008). The Sb atom of the counter-anion is located on an inversion center and has a rhombic distorted octahedral environment with three values of Sb—Cl bond lengths [2.311 (3), 2.374 (2) and 2.393 (4) Å]. Such bond distances are comparable to those observed for similar porphyrin complexes (Soury et al., 2012). The cohesion of the structure is ensured by C—H··· Cl hydrogen bond interactions (Table 1). The crystal packing of compound [Sb(tpp)Cl₂][SbCl₆] is presented in Figure 2.

Related literature top

For general background and the synthesis, see: Liu et al. (1996). For related structures, see: Tsunami et al. (2008); Soury et al. (2012).

Experimental top

The title compound [Sb(tpp)Cl₂][SbCl₆] synthesis was performed under argon atmosphere. SbCl₅ (3–4 cm³) was added to a solution of tetraphenylporphyrin (H₂tpp) (500 mg, 0.814 mmol) in pyridine (25 cm³) and the resulting mixture was refluxed for 1 h. After removing pyridine and excess antimony pentachloride by rotary evaporation, the purple solid obtained was dissolved in dichloromethane and chromatographed on silica gel 60 (100 g, neutral, activity I). The reaction mixture was firstly eluted with CH₂C1₂ to eliminate any free H₂tpp present and then the title compound was eluted as a purple band using CH₂C1₂-methanol (2%). Single red crystals of the title complex, suitable for X-ray diffraction, have been obtained by diffusion of hexanes in dichloromethane solution.

Structure description top

For general background and the synthesis, see: Liu et al. (1996). For related structures, see: Tsunami et al. (2008); Soury et al. (2012).

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level. Hydrogen atoms have been omitted for clarity.
	Fig. 2. A crystal packing diagram of the title compound viewed along the b axis.

Dichlorido(5,10,15,20-tetraphenylporphyrinato-κ⁴N)antimony(V) hexachloridoantimonate(V) top

Crystal data top

[Sb(C₄₄H₂₈N₄)Cl₂][SbCl₆]	Z = 1
M_r = 1139.80	F(000) = 558
Triclinic, P1	D_x = 1.742 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2044 (4) Å	Cell parameters from 22201 reflections
b = 11.1242 (4) Å	θ = 1.9–30.1°
c = 11.3901 (4) Å	µ = 1.77 mm⁻¹
α = 70.685 (2)°	T = 223 K
β = 83.398 (2)°	Prism, red
γ = 63.050 (3)°	0.2 × 0.16 × 0.12 mm
V = 1086.73 (7) Å³

Data collection top

Bruker–Nonius KappaCCD diffractometer	4749 independent reflections
Radiation source: fine-focus sealed tube	4433 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.124
φ & ω scans	θ_max = 27.1°, θ_min = 1.9°
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	h = −13→13
T_min = 0.723, T_max = 0.773	k = −14→14
19871 measured reflections	l = −14→14

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.065	H-atom parameters constrained
wR(F²) = 0.173	w = 1/[σ²(F_o²) + (0.0507P)² + 7.0167P] where P = (F_o² + 2F_c²)/3
S = 1.13	(Δ/σ)_max < 0.001
4749 reflections	Δρ_max = 2.55 e Å⁻³
266 parameters	Δρ_min = −1.45 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (4)

Crystal data top

[Sb(C₄₄H₂₈N₄)Cl₂][SbCl₆]	γ = 63.050 (3)°
M_r = 1139.80	V = 1086.73 (7) Å³
Triclinic, P1	Z = 1
a = 10.2044 (4) Å	Mo Kα radiation
b = 11.1242 (4) Å	µ = 1.77 mm⁻¹
c = 11.3901 (4) Å	T = 223 K
α = 70.685 (2)°	0.2 × 0.16 × 0.12 mm
β = 83.398 (2)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	4749 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	4433 reflections with I > 2σ(I)
T_min = 0.723, T_max = 0.773	R_int = 0.124
19871 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	0 restraints
wR(F²) = 0.173	H-atom parameters constrained
S = 1.13	Δρ_max = 2.55 e Å⁻³
4749 reflections	Δρ_min = −1.45 e Å⁻³
266 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Sb1	0.5000	0.0000	0.5000	0.0226 (2)
N1	0.4725 (5)	0.1913 (5)	0.3693 (4)	0.0259 (9)
N2	0.3841 (5)	0.1056 (5)	0.6238 (4)	0.0261 (9)
Cl1	0.28107 (16)	0.02557 (17)	0.42325 (15)	0.0368 (4)
C1	0.5256 (6)	0.2093 (6)	0.2499 (5)	0.0278 (11)
C2	0.4834 (7)	0.3574 (7)	0.1912 (6)	0.0358 (13)
H2	0.5047	0.3994	0.1098	0.043*
C3	0.4073 (7)	0.4267 (6)	0.2732 (5)	0.0317 (12)
H3	0.3669	0.5251	0.2589	0.038*
C4	0.3993 (6)	0.3234 (6)	0.3857 (5)	0.0270 (11)
C5	0.3287 (6)	0.3531 (5)	0.4932 (5)	0.0265 (11)
C6	0.3224 (6)	0.2509 (6)	0.6023 (5)	0.0273 (11)
C7	0.2497 (6)	0.2797 (6)	0.7118 (6)	0.0312 (12)
H7	0.1987	0.3696	0.7229	0.037*
C8	0.2678 (7)	0.1537 (7)	0.7969 (6)	0.0341 (13)
H8	0.2310	0.1416	0.8774	0.041*
C9	0.3518 (7)	0.0429 (6)	0.7440 (5)	0.0292 (11)
C10	0.3941 (6)	−0.1013 (6)	0.8037 (5)	0.0286 (11)
C11	0.2526 (6)	0.5050 (6)	0.4938 (5)	0.0287 (11)
C12	0.1165 (7)	0.5944 (6)	0.4362 (6)	0.0322 (12)
H12	0.0745	0.5636	0.3899	0.039*
C13	0.0393 (7)	0.7315 (7)	0.4458 (7)	0.0396 (14)
H13	−0.0549	0.7946	0.4082	0.047*
C14	0.1080 (8)	0.7667 (9)	0.5117 (6)	0.0467 (17)
H14	0.0566	0.8583	0.5192	0.056*
C15	0.2426 (8)	0.6865 (7)	0.5688 (8)	0.0437 (16)
H15	0.2841	0.7212	0.6114	0.052*
C16	0.3165 (8)	0.5489 (7)	0.5611 (7)	0.0427 (15)
H16	0.4093	0.4865	0.6015	0.051*
C17	0.3501 (6)	−0.1422 (6)	0.9394 (6)	0.0314 (12)
C18	0.2256 (10)	−0.1633 (11)	0.9654 (7)	0.059 (2)
H18	0.1746	−0.1651	0.9028	0.070*
C19	0.1769 (11)	−0.1821 (12)	1.0868 (8)	0.070 (3)
H19	0.0911	−0.1949	1.1067	0.084*
C20	0.2564 (10)	−0.1816 (8)	1.1781 (7)	0.054 (2)
H20	0.2231	−0.1922	1.2596	0.064*
C21	0.3802 (12)	−0.1662 (12)	1.1503 (7)	0.068 (3)
H21	0.4348	−0.1698	1.2136	0.081*
C22	0.4296 (10)	−0.1447 (11)	1.0289 (7)	0.054 (2)
H22	0.5156	−0.1323	1.0096	0.065*
Sb2	0.0000	0.5000	1.0000	0.0698 (4)
Cl2	−0.2299 (3)	0.5140 (4)	1.0805 (3)	0.0961 (11)
Cl3	0.0724 (3)	0.4837 (5)	1.1918 (3)	0.1218 (17)
Cl4	0.0999 (5)	0.2463 (5)	1.0692 (4)	0.1156 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sb1	0.0246 (3)	0.0192 (3)	0.0262 (3)	−0.0102 (2)	0.00596 (18)	−0.01060 (19)
N1	0.031 (2)	0.020 (2)	0.029 (2)	−0.0120 (19)	0.0057 (18)	−0.0106 (17)
N2	0.030 (2)	0.021 (2)	0.028 (2)	−0.0111 (19)	0.0079 (18)	−0.0115 (17)
Cl1	0.0294 (7)	0.0389 (8)	0.0467 (8)	−0.0157 (6)	0.0003 (6)	−0.0178 (6)
C1	0.030 (3)	0.026 (3)	0.027 (2)	−0.012 (2)	0.007 (2)	−0.009 (2)
C2	0.044 (3)	0.031 (3)	0.032 (3)	−0.020 (3)	0.007 (2)	−0.007 (2)
C3	0.035 (3)	0.021 (3)	0.036 (3)	−0.011 (2)	0.001 (2)	−0.007 (2)
C4	0.027 (3)	0.023 (2)	0.031 (3)	−0.010 (2)	0.005 (2)	−0.010 (2)
C5	0.027 (3)	0.018 (2)	0.036 (3)	−0.008 (2)	0.003 (2)	−0.013 (2)
C6	0.029 (3)	0.023 (2)	0.033 (3)	−0.011 (2)	0.004 (2)	−0.013 (2)
C7	0.032 (3)	0.027 (3)	0.036 (3)	−0.010 (2)	0.011 (2)	−0.020 (2)
C8	0.039 (3)	0.034 (3)	0.033 (3)	−0.016 (3)	0.014 (2)	−0.020 (2)
C9	0.031 (3)	0.031 (3)	0.029 (3)	−0.014 (2)	0.011 (2)	−0.016 (2)
C10	0.031 (3)	0.026 (3)	0.031 (3)	−0.014 (2)	0.007 (2)	−0.012 (2)
C11	0.030 (3)	0.027 (3)	0.032 (3)	−0.014 (2)	0.008 (2)	−0.013 (2)
C12	0.028 (3)	0.025 (3)	0.042 (3)	−0.007 (2)	0.001 (2)	−0.014 (2)
C13	0.027 (3)	0.029 (3)	0.060 (4)	−0.005 (2)	0.002 (3)	−0.021 (3)
C14	0.034 (3)	0.064 (5)	0.043 (3)	−0.032 (3)	0.002 (3)	−0.003 (3)
C15	0.037 (3)	0.032 (3)	0.070 (5)	−0.012 (3)	−0.003 (3)	−0.030 (3)
C16	0.039 (3)	0.030 (3)	0.062 (4)	−0.010 (3)	−0.008 (3)	−0.021 (3)
C17	0.026 (3)	0.022 (2)	0.046 (3)	−0.008 (2)	0.003 (2)	−0.016 (2)
C18	0.061 (5)	0.096 (7)	0.046 (4)	−0.056 (5)	0.021 (4)	−0.029 (4)
C19	0.056 (5)	0.093 (7)	0.054 (5)	−0.040 (5)	0.025 (4)	−0.013 (5)
C20	0.072 (5)	0.045 (4)	0.035 (3)	−0.025 (4)	0.023 (3)	−0.012 (3)
C21	0.090 (7)	0.098 (8)	0.034 (4)	−0.055 (6)	0.015 (4)	−0.028 (4)
C22	0.055 (5)	0.088 (6)	0.038 (3)	−0.048 (5)	0.013 (3)	−0.023 (4)
Sb2	0.0346 (4)	0.1176 (8)	0.0807 (6)	−0.0245 (4)	0.0141 (4)	−0.0767 (6)
Cl2	0.0491 (13)	0.171 (3)	0.110 (2)	−0.0501 (17)	0.0332 (13)	−0.103 (2)
Cl3	0.0586 (15)	0.222 (5)	0.119 (2)	−0.039 (2)	0.0162 (15)	−0.133 (3)
Cl4	0.116 (3)	0.121 (3)	0.112 (3)	−0.034 (2)	0.039 (2)	−0.075 (2)

Geometric parameters (Å, º) top

Sb1—N2ⁱ	2.054 (4)	C11—C16	1.379 (9)
Sb1—N2	2.054 (4)	C12—C13	1.400 (8)
Sb1—N1	2.070 (4)	C12—H12	0.9400
Sb1—N1ⁱ	2.070 (4)	C13—C14	1.332 (10)
Sb1—Cl1ⁱ	2.3547 (14)	C13—H13	0.9400
Sb1—Cl1	2.3547 (14)	C14—C15	1.347 (10)
N1—C4	1.380 (7)	C14—H14	0.9400
N1—C1	1.390 (7)	C15—C16	1.396 (9)
N2—C6	1.386 (7)	C15—H15	0.9400
N2—C9	1.394 (7)	C16—H16	0.9400
C1—C10ⁱ	1.402 (8)	C17—C22	1.359 (10)
C1—C2	1.429 (8)	C17—C18	1.377 (10)
C2—C3	1.356 (9)	C18—C19	1.395 (11)
C2—H2	0.9400	C18—H18	0.9400
C3—C4	1.434 (8)	C19—C20	1.394 (14)
C3—H3	0.9400	C19—H19	0.9400
C4—C5	1.406 (8)	C20—C21	1.339 (13)
C5—C6	1.398 (8)	C20—H20	0.9400
C5—C11	1.508 (7)	C21—C22	1.398 (10)
C6—C7	1.430 (8)	C21—H21	0.9400
C7—C8	1.359 (9)	C22—H22	0.9400
C7—H7	0.9400	Sb2—Cl3	2.311 (3)
C8—C9	1.426 (8)	Sb2—Cl3ⁱⁱ	2.311 (3)
C8—H8	0.9400	Sb2—Cl2ⁱⁱ	2.374 (2)
C9—C10	1.393 (8)	Sb2—Cl2	2.374 (2)
C10—C1ⁱ	1.402 (8)	Sb2—Cl4	2.393 (4)
C10—C17	1.536 (8)	Sb2—Cl4ⁱⁱ	2.393 (4)
C11—C12	1.369 (8)

N2ⁱ—Sb1—N2	180.00 (16)	C12—C11—C16	120.6 (6)
N2ⁱ—Sb1—N1	90.19 (18)	C12—C11—C5	120.1 (5)
N2—Sb1—N1	89.81 (18)	C16—C11—C5	119.1 (5)
N2ⁱ—Sb1—N1ⁱ	89.81 (18)	C11—C12—C13	120.5 (6)
N2—Sb1—N1ⁱ	90.19 (18)	C11—C12—H12	119.8
N1—Sb1—N1ⁱ	180.0 (2)	C13—C12—H12	119.8
N2ⁱ—Sb1—Cl1ⁱ	90.57 (14)	C14—C13—C12	115.6 (7)
N2—Sb1—Cl1ⁱ	89.43 (14)	C14—C13—H13	122.2
N1—Sb1—Cl1ⁱ	89.98 (14)	C12—C13—H13	122.2
N1ⁱ—Sb1—Cl1ⁱ	90.02 (14)	C13—C14—C15	127.7 (8)
N2ⁱ—Sb1—Cl1	89.43 (14)	C13—C14—H14	116.2
N2—Sb1—Cl1	90.57 (14)	C15—C14—H14	116.2
N1—Sb1—Cl1	90.02 (14)	C14—C15—C16	116.0 (7)
N1ⁱ—Sb1—Cl1	89.98 (14)	C14—C15—H15	122.0
Cl1ⁱ—Sb1—Cl1	180.0	C16—C15—H15	122.0
C4—N1—C1	108.0 (4)	C11—C16—C15	119.6 (6)
C4—N1—Sb1	126.0 (4)	C11—C16—H16	120.2
C1—N1—Sb1	126.0 (4)	C15—C16—H16	120.2
C6—N2—C9	108.0 (4)	C22—C17—C18	122.1 (6)
C6—N2—Sb1	126.3 (4)	C22—C17—C10	118.2 (6)
C9—N2—Sb1	125.6 (4)	C18—C17—C10	119.5 (6)
N1—C1—C10ⁱ	126.1 (5)	C17—C18—C19	118.5 (8)
N1—C1—C2	107.9 (5)	C17—C18—H18	120.7
C10ⁱ—C1—C2	126.0 (5)	C19—C18—H18	120.7
C3—C2—C1	108.1 (5)	C20—C19—C18	119.4 (8)
C3—C2—H2	125.9	C20—C19—H19	120.3
C1—C2—H2	125.9	C18—C19—H19	120.3
C2—C3—C4	107.9 (5)	C21—C20—C19	120.4 (7)
C2—C3—H3	126.0	C21—C20—H20	119.8
C4—C3—H3	126.0	C19—C20—H20	119.8
N1—C4—C5	126.6 (5)	C20—C21—C22	121.1 (8)
N1—C4—C3	108.1 (5)	C20—C21—H21	119.4
C5—C4—C3	125.4 (5)	C22—C21—H21	119.4
C6—C5—C4	124.6 (5)	C17—C22—C21	118.4 (7)
C6—C5—C11	116.2 (5)	C17—C22—H22	120.8
C4—C5—C11	119.2 (5)	C21—C22—H22	120.8
N2—C6—C5	126.6 (5)	Cl3—Sb2—Cl3ⁱⁱ	180.000 (1)
N2—C6—C7	108.1 (5)	Cl3—Sb2—Cl2ⁱⁱ	90.36 (11)
C5—C6—C7	125.3 (5)	Cl3ⁱⁱ—Sb2—Cl2ⁱⁱ	89.64 (11)
C8—C7—C6	107.7 (5)	Cl3—Sb2—Cl2	89.64 (11)
C8—C7—H7	126.2	Cl3ⁱⁱ—Sb2—Cl2	90.36 (11)
C6—C7—H7	126.2	Cl2ⁱⁱ—Sb2—Cl2	180.0
C7—C8—C9	108.7 (5)	Cl3—Sb2—Cl4	87.99 (16)
C7—C8—H8	125.7	Cl3ⁱⁱ—Sb2—Cl4	92.01 (16)
C9—C8—H8	125.7	Cl2ⁱⁱ—Sb2—Cl4	90.45 (14)
C10—C9—N2	127.0 (5)	Cl2—Sb2—Cl4	89.55 (14)
C10—C9—C8	125.5 (5)	Cl3—Sb2—Cl4ⁱⁱ	92.01 (16)
N2—C9—C8	107.5 (5)	Cl3ⁱⁱ—Sb2—Cl4ⁱⁱ	87.99 (16)
C9—C10—C1ⁱ	125.1 (5)	Cl2ⁱⁱ—Sb2—Cl4ⁱⁱ	89.55 (14)
C9—C10—C17	116.2 (5)	Cl2—Sb2—Cl4ⁱⁱ	90.45 (14)
C1ⁱ—C10—C17	118.7 (5)	Cl4—Sb2—Cl4ⁱⁱ	180.000 (1)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl3ⁱⁱ	0.94	2.76	3.490 (8)	135
C8—H8···Cl4	0.94	2.74	3.593 (8)	151
C12—H12···Cl3ⁱⁱⁱ	0.94	2.69	3.539 (8)	151

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cl3ⁱ	0.94	2.76	3.490 (8)	135
C8—H8···Cl4	0.94	2.74	3.593 (8)	151
C12—H12···Cl3ⁱⁱ	0.94	2.69	3.539 (8)	151

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

Acknowledgements

The authors gratefully acknowledge financial support from the Ministry of Higher Education and Scientific Research of Tunisia.

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