catena-Poly[bis­(1,3-benzo­thia­zol-3-ium) [[di­chlorido­anti­monate(III)]-di-μ-chlorido-μ-oxido-[chlorido­anti­monate(III)]-μ-chlorido]]

The title compound, {(C₇H₆NS)₂[Sb₂Cl₆O]}_n, contains two benzo­thia­zolidium cations and one tri-μ-chlorido-tri­chlorido-μ-oxido-di­anti­monate(III) anion. The structure of the inorganic cation may be described as as being built up from two polyhedra, i.e. a square-pyramidal SbCl₄O and a distorted octa­hedral SbOCl₅ unit, sharing a common face (comprising the O atom and two Cl atoms). The two benzo­thia­zole cations are quasi-planar and subtend a dihedral angle of 19.93 (5)°. The crystal packing can be described by alternating (100) layers and [001] chains of the organic cations and inorganic anions connected through an extensive three-dimensional network of N—H⋯Cl, C—H⋯O and C—H⋯Cl hydrogen bonds. This is consolidated by slipped π–π stacking, with centroid-to-centroid distances between the benzo­thia­zole rings of 3.7111 (18)–3.8452 (16) Å. These inter­actions link the mol­ecules within the layers and also link the layers together and reinforce the cohesion of the ionic structure.

1. Chemical context

The coordination chemistry of anti­mony has both a practical and theoretical inter­est (Abboud et al., 2007; Bujak & Angel, 2006). Recently, the use of anti­mony complexes in cancer chemotherapy has become a topic of inter­est (Demicheli et al., 2006; Rais et al., 2000). As part of our ongoing studies of benzo­thia­zole-based coordination networks (Bouchareb et al., 2014), we now report the polymeric structure of new organic–inorganic hybrid compound {(C₇H₆NS)₂[Sb₂Cl₆O]}_n, (I).

2. Structural commentary

The title compound contains two benzo­thia­zolidium cations and one tri-μ-chlorido-tri­chlorido-μ-oxido-di­anti­monate(III) anion (Sb₂Cl₆O²⁻). The mol­ecular geometry and the atom-numbering scheme are shown in Fig. 1.

Figure 1 The asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

The structure of the inorganic anion may be described as two polyhedra, square-pyramidal SbCl₄O and distorted octa­hedral SbOCl₅, sharing a common face (O1, Cl5 and Cl6). In the first polyhedron, four Cl atoms (Cl3–Cl4–Cl5–Cl6) form a basal plane with the Sb1 atom lying 0.3011 (2) Å below the plane. The apical position is occupied by the O1 atom. In the second polyhedron, the O1 atom occupies the apical position and four Cl atoms (Cl1–Cl2–Cl5–Cl6) form the base equatorial plane with Sb2 displaced by 0.4168 (1) Å from it. The geometry of the Sb2 atom can be described as distorted octa­hedral, a sixth coordination is observed at a longer distance, with Sb2 coordinated by the adjacent Cl3ⁱ atom at a distance of 3.546 (4) Å [symmetry code: (i)  − x,  + y,  − z], forming an infinite chain parallel to [001] (Fig. 2). This distance is significantly shorter than the sum of the relevant van der Waals radii of 4.01 Å (rSb = 2.1 Å and rCl = 1.91 Å) and in good agreement with those found in [SbCl₃(C₂₅H₂₂O₂P₂)] (Razak et al., 1999) and in [(CH₃)₂NH(CH₂)₂NH₃][SbCl₅] (Bujak & Angel, 2006). In this mol­ecule, the angle between the two equatorial planes is 75.86 (2)°.

Figure 2 View of a polymeric chain of Sb2Cl6O along the c axis.

The Sb—O bridge distances of 1.9404 (16) and 1.9460 (17) Å are similar to those found in the Sb₂Cl₆O₂ moiety (Abboud et al., 2007). Excluding the longest bond (Sb2—Cl3ⁱ), the terminal Sb—Cl bonds are in the range 2.3974 (8)–2.4982 (8) Å and are shorter than the bridging bonds [2.7522 (8)–3.3244 (9) Å] and are in good agreement with those found in C₂₆H₂₈N₈O₆Sb₄Cl₁₀ (Abboud et al., 2007). However, the Sb—O—Sb bond angle is 123.56 (9)° which is very different to that observed in Cs₂Sb₂O₂(OH)₈ (Mikhaylov et al., 2011) and the Sb₂Cl₆O₂ moiety (Abboud et al., 2007). The dihedral angle between the mean planes of the two benzo­thia­zole cations is 19.93 (5)°.

3. Supra­molecular features

The crystal packing can be described by alternating (100) layers and [001] chains of organic cations and inorganic anions connected through an extensive network of N—H⋯Cl, C—H⋯O and C—H⋯Cl hydrogen bonds, leading to the formation of a three-dimensional network (Table 1, Fig. 3). The packing is consolidated by slipped π–π stacking with centroid-to-centroid distances of 3.7111 (18)–3.8452 (16) Å between the benzo­thia­zole rings. These inter­actions link the mol­ecules within the layers and also link the layers together, reinforcing the cohesion of the ionic structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯Cl6^i	0.86	2.37	3.200 (3)	162
N2—H2N⋯Cl6^ii	0.86	2.35	3.145 (3)	153
C1—H1⋯O1	0.93	2.27	3.152 (4)	159
C8—H8⋯Cl5^iii	0.93	2.72	3.327 (3)	124
C10—H10⋯Cl3^iv	0.93	2.78	3.612 (3)	150
C13—H13⋯Cl2^ii	0.93	2.76	3.524 (3)	140
Symmetry codes: (i) ; (ii) ; (iii) x+1, y, z; (iv) .

Figure 3 Part of diagram packing of the title compound, viewed along the a axis, showing alternating chains and layers connected by N—H⋯Cl and C—H⋯Cl hydrogen bonds (shown as dashed lines).

4. Synthesis and crystallization

A solution of SbCl₃ (45.6 mg, 0.2 mmol) in water (10 ml) was added dropwise to a solution of benzo­thia­zole (0.5 ml, 4.6 mmol) in ethanol (10 ml). The mixture was then refluxed with stirring for 3 h and the resulting solution was left to stand at room temperature. Colorless crystals were obtained after several days.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Approximate positions for all H atoms were first obtained from the difference electron density map. However, the H atoms were placed into idealized positions and refined using the riding-atom approximation. The applied constraints were: C—H = 0.93 Å and N—H = 0.86 Å, U_iso = 1.2U_eq(C or N).

Table 2
Experimental details

Crystal data
Chemical formula	(C7H6NS)2[Sb2Cl6O]
Mr	744.58
Crystal system, space group	Monoclinic, P21/c
Temperature (K)	295
a, b, c (Å)	10.2826 (2), 16.2448 (3), 14.9849 (3)
β (°)	111.674 (1)
V (Å^3)	2326.09 (8)
Z	4
Radiation type	Mo Kα
μ (mm^−1)	3.20
Crystal size (mm)	0.17 × 0.13 × 0.11
Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2002)
Tmin, Tmax	0.630, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	20349, 5344, 4627
Rint	0.026
(sin θ/λ)max (Å^−1)	0.651
Refinement
R[F^2 > 2σ(F^2)], wR(F^2), S	0.022, 0.050, 1.02
No. of reflections	5344
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρmax, Δρmin (e Å^−3)	0.54, −0.77
Computer programs: APEX2 and SAINT (Bruker, 2011), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows and WinGX (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001).

Supporting information

S1. Chemical context

The coordination chemistry of anti­mony has both a practical and theoretical inter­est (Abboud et al., 2007, Bujak & Angel, 2006). Recently, the use of anti­mony complexes in cancer chemotherapy has become a topic of inter­est (Demicheli et al., 2006; Rais et al., 2000). As part of our ongoing studies of benzo­thia­zole-based coordination networks (Bouchareb et al., 2014), we now report the structure of new organic–inorganic hybrid compound {(C₇H₆NS)₂[Sb₂Cl₆O]}_n, (I).

S2. Structural commentary

The title compound contains two benzo­thia­zolidium cations and one tri-µ-chlorido-trichlorido-µ-oxido-di­anti­monate(III) anion (Sb₂Cl₆O₂⁻). The molecular geometry and the atom-numbering scheme are shown in Fig 1.

The structure of the inorganic cation may be described as two polyhedra, square-pyramidal SbCl₄O and distorted o­cta­hedral SbOCl₅, sharing a common face (O1, Cl5 and Cl6). In the first polyhedron, four Cl atoms (Cl3–Cl4–Cl5–Cl6) form a basal plane with the Sb1 atom lying 0.3011 (2) Å below the plane. The apical position is occupied by the O1 atom. In the second polyhedron, the O1 atom occupies the apical position and four Cl atoms (Cl1–Cl2–Cl5–Cl6) form the base equatorial plane with Sb2 displaced by 0.4168 (1) Å from it. The geometry of the Sb2 atom can be described as distorted o­cta­hedral, a sixth coordination is observed at a longer distance, with Sb2 coordinated by the adjacent Cl3ⁱ atom at a distance of 3.546 (4) Å [symmetry code: (i) 1/2 − x, 1/2 + y, 1/2 − z], forming an infinite chain parallel to [001] (Fig. 2). This distance is significantly shorter than the sum of the relevant van der Waals radii of 4.01 Å (rSb = 2.1 Å and rCl = 1.91 Å) but in good agreement with those found in [SbCl₃(C₂₅H₂₂O₂P₂)] (Razak et al., 1999) and in [(CH₃)2NH(CH₂)2NH₃][SbCl₅] (Bujak et al., 2006). In this molecule, the angle between the two equatorial planes is 75.86 (2)°.

The Sb—O bridge distances of 1.9404 (16) and 1.9460 (17) Å and are similar to those found in the Sb₂Cl₆O₂ moiety (Abboud et al. 2007). Excluding the longest bond (Sb2—Cl3ⁱ), the terminal Sb—Cl bonds are in the range 2.3974 (8)–2.4982 (8) Å and are shorter than the bridging bonds [2.7522 (8)–3.3244 (9) Å] and are in good agreement with those found in C₂₆H₂₈N₈O₆Sb₄Cl₁₀ (Abboud et al. 2007). However, the Sb—O—Sb bond angle is 123.56 (9)° which is very different to that observed in Cs₂Sb₂O₂(OH)₈ (Mikhaylov et al., 2011) and the Sb₂Cl₆O₂ moiety (Abboud et al. 2007). The dihedral angle between the mean planes of the two benzo­thia­zole cations is 19.93 (5)°.

S3. Supra­molecular features

The crystal packing can be described by alternating layers and chains of organic cations and inorganic anions connected through an extensive network of N—H···Cl and C—H···Cl hydrogen bonds, leading to the formation of a three-dimensional network (Table 1, Fig. 3). The packing is consolidated by slipped π–π stacking with centroid-to-centroid distances of 3.7111 (18)–3.8452 (16) Å between the benzo­thia­zole rings. These inter­actions link the molecules within the layers and also link the layers together, reinforcing the cohesion of the ionic structure.

S4. Synthesis and crystallization

A solution of SbCl₃ (45.6 mg, 0.2 mmol) in water (10 ml) was added dropwise to a solution of benzo­thia­zole (0.5 ml, 4.6 mmol) in ethanol (10 ml). The mixture was then refluxed with stirring for 3 h and the resulting solution was left to stand at room temperature. Colorless crystals were obtained after several days.

S5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. A l l non-H atoms were refined with anisotropic atomic displacement parameters. Approximate positions for all H atoms were first obtained from the difference electron density map. However, the H atoms were placed into idealized positions and refined using the riding-atom approximation. The applied constraints were: C—H = 0.93 Å and N—H = 0.86 Å, U_iso = 1.2U_eq(C or N).

Related literature

For background environment of Sb, see: Mikhaylov et al. (2011); Bujak et al. (2006); Razak et al. (1999); Abboud et al. (2007). For the use of antimony complexes in cancer chemotherapy, see: Rais et al. (2000) and Demicheli et al. (2006). For our recent work on the design and synthesis of benzothiazole coordination networks, see: Bouchareb et al. (2014).

Structure description

The coordination chemistry of anti­mony has both a practical and theoretical inter­est (Abboud et al., 2007, Bujak & Angel, 2006). Recently, the use of anti­mony complexes in cancer chemotherapy has become a topic of inter­est (Demicheli et al., 2006; Rais et al., 2000). As part of our ongoing studies of benzo­thia­zole-based coordination networks (Bouchareb et al., 2014), we now report the structure of new organic–inorganic hybrid compound {(C₇H₆NS)₂[Sb₂Cl₆O]}_n, (I).

The title compound contains two benzo­thia­zolidium cations and one tri-µ-chlorido-trichlorido-µ-oxido-di­anti­monate(III) anion (Sb₂Cl₆O₂⁻). The molecular geometry and the atom-numbering scheme are shown in Fig 1.

The structure of the inorganic cation may be described as two polyhedra, square-pyramidal SbCl₄O and distorted o­cta­hedral SbOCl₅, sharing a common face (O1, Cl5 and Cl6). In the first polyhedron, four Cl atoms (Cl3–Cl4–Cl5–Cl6) form a basal plane with the Sb1 atom lying 0.3011 (2) Å below the plane. The apical position is occupied by the O1 atom. In the second polyhedron, the O1 atom occupies the apical position and four Cl atoms (Cl1–Cl2–Cl5–Cl6) form the base equatorial plane with Sb2 displaced by 0.4168 (1) Å from it. The geometry of the Sb2 atom can be described as distorted o­cta­hedral, a sixth coordination is observed at a longer distance, with Sb2 coordinated by the adjacent Cl3ⁱ atom at a distance of 3.546 (4) Å [symmetry code: (i) 1/2 − x, 1/2 + y, 1/2 − z], forming an infinite chain parallel to [001] (Fig. 2). This distance is significantly shorter than the sum of the relevant van der Waals radii of 4.01 Å (rSb = 2.1 Å and rCl = 1.91 Å) but in good agreement with those found in [SbCl₃(C₂₅H₂₂O₂P₂)] (Razak et al., 1999) and in [(CH₃)2NH(CH₂)2NH₃][SbCl₅] (Bujak et al., 2006). In this molecule, the angle between the two equatorial planes is 75.86 (2)°.

The Sb—O bridge distances of 1.9404 (16) and 1.9460 (17) Å and are similar to those found in the Sb₂Cl₆O₂ moiety (Abboud et al. 2007). Excluding the longest bond (Sb2—Cl3ⁱ), the terminal Sb—Cl bonds are in the range 2.3974 (8)–2.4982 (8) Å and are shorter than the bridging bonds [2.7522 (8)–3.3244 (9) Å] and are in good agreement with those found in C₂₆H₂₈N₈O₆Sb₄Cl₁₀ (Abboud et al. 2007). However, the Sb—O—Sb bond angle is 123.56 (9)° which is very different to that observed in Cs₂Sb₂O₂(OH)₈ (Mikhaylov et al., 2011) and the Sb₂Cl₆O₂ moiety (Abboud et al. 2007). The dihedral angle between the mean planes of the two benzo­thia­zole cations is 19.93 (5)°.

The crystal packing can be described by alternating layers and chains of organic cations and inorganic anions connected through an extensive network of N—H···Cl and C—H···Cl hydrogen bonds, leading to the formation of a three-dimensional network (Table 1, Fig. 3). The packing is consolidated by slipped π–π stacking with centroid-to-centroid distances of 3.7111 (18)–3.8452 (16) Å between the benzo­thia­zole rings. These inter­actions link the molecules within the layers and also link the layers together, reinforcing the cohesion of the ionic structure.

For background environment of Sb, see: Mikhaylov et al. (2011); Bujak et al. (2006); Razak et al. (1999); Abboud et al. (2007). For the use of antimony complexes in cancer chemotherapy, see: Rais et al. (2000) and Demicheli et al. (2006). For our recent work on the design and synthesis of benzothiazole coordination networks, see: Bouchareb et al. (2014).

Synthesis and crystallization

A solution of SbCl₃ (45.6 mg, 0.2 mmol) in water (10 ml) was added dropwise to a solution of benzo­thia­zole (0.5 ml, 4.6 mmol) in ethanol (10 ml). The mixture was then refluxed with stirring for 3 h and the resulting solution was left to stand at room temperature. Colorless crystals were obtained after several days.

Refinement details

Crystal data, data collection and structure refinement details are summarized in Table 2. A l l non-H atoms were refined with anisotropic atomic displacement parameters. Approximate positions for all H atoms were first obtained from the difference electron density map. However, the H atoms were placed into idealized positions and refined using the riding-atom approximation. The applied constraints were: C—H = 0.93 Å and N—H = 0.86 Å, U_iso = 1.2U_eq(C or N).

Computing details

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); program(s) used to solve structure: SIR2002 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures

	Fig. 1. The asymmetric unit of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. View of a polymeric chain of Sb2Cl6O along the c axis.
	Fig. 3. Part of diagram packing of the title compound, viewed along the a axis, showing alternating chains and layers connecting by N—H···Cl and C—H···Cl hydrogen bonds (shown as dashed lines).

catena-Poly[1,3-benzothiazol-3-ium [[dichloridoantimonate(III)]-di-µ-chlorido-µ-oxido-[chloridoantimonate(III)]-µ-chlorido]]

Crystal data

(C7H6NS)2[Sb2Cl6O]	F(000) = 1416
Mr = 744.58	Dx = 2.126 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8790 reflections
a = 10.2826 (2) Å	θ = 2.5–27.5°
b = 16.2448 (3) Å	µ = 3.20 mm^−1
c = 14.9849 (3) Å	T = 295 K
β = 111.674 (1)°	Block, colorless
V = 2326.09 (8) Å^3	0.17 × 0.13 × 0.11 mm
Z = 4

Data collection

Bruker APEXII CCD diffractometer	5344 independent reflections
Radiation source: sealed tube	4627 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 2002)	h = −11→13
Tmin = 0.630, Tmax = 0.746	k = −19→21
20349 measured reflections	l = −19→18

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.050	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0186P)^2 + 1.5448P] where P = (Fo^2 + 2Fc^2)/3
5344 reflections	(Δ/σ)max = 0.001
244 parameters	Δρmax = 0.54 e Å^−3
0 restraints	Δρmin = −0.77 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.36748 (12)	0.17148 (5)	0.98344 (7)	0.0662 (3)
N1	0.1904 (3)	0.05865 (18)	0.94373 (19)	0.0539 (7)
H1N	0.114	0.0319	0.9156	0.065*
C1	0.2113 (4)	0.1303 (2)	0.9189 (2)	0.0653 (10)
H1	0.1448	0.1582	0.8683	0.078*
C2	0.4125 (3)	0.08232 (16)	1.05140 (19)	0.0386 (6)
C3	0.5374 (3)	0.0621 (2)	1.1261 (2)	0.0509 (8)
H3	0.612	0.0988	1.147	0.061*
C4	0.5459 (3)	−0.0141 (2)	1.1676 (2)	0.0528 (8)
H4	0.6282	−0.0293	1.2172	0.063*
C5	0.4350 (4)	−0.0684 (2)	1.1374 (2)	0.0516 (8)
H5	0.4439	−0.1191	1.1678	0.062*
C6	0.3131 (3)	−0.04978 (18)	1.0645 (2)	0.0474 (7)
H6	0.2391	−0.087	1.0443	0.057*
C7	0.3030 (3)	0.02653 (17)	1.02135 (19)	0.0372 (6)
S2	0.52690 (8)	0.11063 (4)	0.59703 (6)	0.04448 (17)
N2	0.7036 (2)	0.00265 (15)	0.68158 (18)	0.0436 (6)
H2N	0.7828	−0.0203	0.7127	0.052*
C8	0.6923 (3)	0.07956 (18)	0.6561 (2)	0.0465 (7)
H8	0.769	0.1143	0.6695	0.056*
C9	0.4653 (3)	0.01241 (16)	0.60657 (18)	0.0339 (6)
C10	0.3292 (3)	−0.01737 (19)	0.5748 (2)	0.0431 (7)
H10	0.2533	0.0166	0.5433	0.052*
C11	0.3111 (3)	−0.0985 (2)	0.5917 (2)	0.0501 (7)
H11	0.2208	−0.1199	0.5712	0.06*
C12	0.4237 (3)	−0.15006 (19)	0.6385 (2)	0.0530 (8)
H12	0.4069	−0.205	0.6482	0.064*
C13	0.5579 (3)	−0.12215 (18)	0.6705 (2)	0.0481 (7)
H13	0.6331	−0.1567	0.7016	0.058*
C14	0.5770 (3)	−0.03964 (16)	0.65440 (19)	0.0359 (6)
Sb1	−0.067085 (18)	0.323213 (10)	0.767483 (12)	0.03143 (5)
Sb2	0.053422 (18)	0.221298 (11)	0.613337 (12)	0.03397 (5)
Cl1	0.01992 (9)	0.07748 (5)	0.63368 (7)	0.0589 (2)
Cl2	0.30403 (7)	0.20616 (5)	0.68094 (6)	0.05062 (18)
Cl3	0.13613 (8)	0.35386 (5)	0.91846 (5)	0.05065 (18)
Cl4	−0.14276 (8)	0.21318 (5)	0.84967 (6)	0.05007 (18)
Cl5	−0.24438 (8)	0.26668 (4)	0.59142 (6)	0.04931 (18)
O1	0.05721 (19)	0.24501 (12)	0.74157 (12)	0.0391 (4)
Cl6	0.04721 (8)	0.42304 (5)	0.64881 (6)	0.0558 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0921 (7)	0.0379 (4)	0.0703 (6)	0.0017 (4)	0.0319 (5)	0.0061 (4)
N1	0.0376 (13)	0.0731 (19)	0.0455 (15)	0.0001 (13)	0.0092 (12)	−0.0065 (14)
C1	0.073 (2)	0.071 (2)	0.0456 (19)	0.042 (2)	0.0148 (18)	0.0111 (17)
C2	0.0497 (16)	0.0334 (13)	0.0350 (15)	−0.0018 (12)	0.0181 (13)	−0.0021 (11)
C3	0.0474 (17)	0.062 (2)	0.0414 (17)	−0.0141 (15)	0.0139 (14)	−0.0112 (15)
C4	0.0485 (18)	0.076 (2)	0.0313 (15)	0.0127 (17)	0.0116 (14)	0.0045 (15)
C5	0.070 (2)	0.0477 (17)	0.0422 (17)	0.0085 (16)	0.0267 (17)	0.0122 (14)
C6	0.0581 (19)	0.0430 (16)	0.0458 (17)	−0.0131 (14)	0.0247 (15)	−0.0014 (13)
C7	0.0363 (14)	0.0440 (15)	0.0308 (14)	0.0019 (12)	0.0117 (12)	−0.0024 (11)
S2	0.0533 (4)	0.0327 (3)	0.0566 (5)	0.0085 (3)	0.0310 (4)	0.0065 (3)
N2	0.0318 (12)	0.0456 (13)	0.0510 (15)	0.0069 (11)	0.0125 (11)	−0.0009 (11)
C8	0.0454 (17)	0.0419 (16)	0.060 (2)	−0.0037 (13)	0.0282 (15)	−0.0071 (14)
C9	0.0385 (14)	0.0333 (13)	0.0329 (14)	0.0054 (11)	0.0168 (12)	0.0027 (11)
C10	0.0368 (15)	0.0549 (18)	0.0368 (15)	0.0077 (13)	0.0125 (12)	0.0067 (13)
C11	0.0422 (16)	0.061 (2)	0.0444 (17)	−0.0152 (15)	0.0135 (14)	−0.0025 (15)
C12	0.062 (2)	0.0387 (16)	0.058 (2)	−0.0107 (15)	0.0214 (17)	0.0041 (14)
C13	0.0533 (18)	0.0384 (15)	0.0495 (18)	0.0097 (14)	0.0153 (15)	0.0106 (13)
C14	0.0344 (13)	0.0375 (14)	0.0357 (14)	0.0054 (11)	0.0127 (12)	0.0011 (11)
Sb1	0.03409 (9)	0.02825 (9)	0.03458 (10)	0.00560 (7)	0.01575 (7)	−0.00018 (7)
Sb2	0.03473 (10)	0.04105 (10)	0.02678 (9)	0.00516 (8)	0.01211 (7)	−0.00064 (7)
Cl1	0.0568 (5)	0.0425 (4)	0.0830 (6)	−0.0050 (4)	0.0325 (4)	−0.0093 (4)
Cl2	0.0351 (4)	0.0611 (5)	0.0567 (5)	0.0025 (3)	0.0181 (3)	−0.0138 (4)
Cl3	0.0601 (5)	0.0487 (4)	0.0381 (4)	−0.0131 (4)	0.0122 (3)	−0.0065 (3)
Cl4	0.0570 (4)	0.0486 (4)	0.0529 (4)	−0.0093 (3)	0.0301 (4)	0.0031 (3)
Cl5	0.0457 (4)	0.0430 (4)	0.0491 (4)	−0.0024 (3)	0.0057 (3)	0.0020 (3)
O1	0.0460 (11)	0.0463 (11)	0.0271 (9)	0.0225 (9)	0.0160 (8)	0.0044 (8)
Cl6	0.0466 (4)	0.0579 (5)	0.0518 (5)	−0.0107 (4)	0.0051 (4)	0.0103 (4)

Geometric parameters (Å, º)

S1—C1	1.678 (4)	C8—H8	0.93
S1—C2	1.732 (3)	C9—C10	1.388 (4)
N1—C1	1.265 (4)	C9—C14	1.393 (3)
N1—C7	1.404 (4)	C10—C11	1.368 (4)
N1—H1N	0.8599	C10—H10	0.93
C1—H1	0.93	C11—C12	1.391 (4)
C2—C7	1.385 (4)	C11—H11	0.93
C2—C3	1.396 (4)	C12—C13	1.360 (4)
C3—C4	1.373 (5)	C12—H12	0.93
C3—H3	0.93	C13—C14	1.389 (4)
C4—C5	1.379 (4)	C13—H13	0.93
C4—H4	0.93	Sb1—O1	1.9404 (16)
C5—C6	1.358 (4)	Sb1—Cl4	2.4545 (7)
C5—H5	0.93	Sb1—Cl3	2.4982 (8)
C6—C7	1.384 (4)	Sb1—Cl5	2.7522 (8)
C6—H6	0.93	Sb1—Cl6	2.9524 (8)
S2—C8	1.679 (3)	Sb2—O1	1.9460 (17)
S2—C9	1.742 (3)	Sb2—Cl1	2.3974 (8)
N2—C8	1.299 (4)	Sb2—Cl2	2.4081 (7)
N2—C14	1.392 (3)	Sb2—Cl5	3.0473 (8)
N2—H2N	0.8599	Sb2—Cl6	3.3244 (9)
C1—S1—C2	89.81 (16)	C9—C10—H10	121.2
C1—N1—C7	114.1 (3)	C10—C11—C12	121.9 (3)
C1—N1—H1N	123	C10—C11—H11	119.1
C7—N1—H1N	122.9	C12—C11—H11	119.1
N1—C1—S1	115.3 (3)	C13—C12—C11	121.6 (3)
N1—C1—H1	122.3	C13—C12—H12	119.2
S1—C1—H1	122.3	C11—C12—H12	119.2
C7—C2—C3	120.2 (3)	C12—C13—C14	116.8 (3)
C7—C2—S1	110.3 (2)	C12—C13—H13	121.6
C3—C2—S1	129.4 (2)	C14—C13—H13	121.6
C4—C3—C2	117.5 (3)	C13—C14—N2	127.1 (3)
C4—C3—H3	121.3	C13—C14—C9	122.1 (3)
C2—C3—H3	121.3	N2—C14—C9	110.8 (2)
C3—C4—C5	121.4 (3)	O1—Sb1—Cl4	88.74 (6)
C3—C4—H4	119.3	O1—Sb1—Cl3	85.37 (6)
C5—C4—H4	119.3	Cl4—Sb1—Cl3	90.28 (3)
C6—C5—C4	121.8 (3)	O1—Sb1—Cl5	80.90 (6)
C6—C5—H5	119.1	Cl4—Sb1—Cl5	91.00 (3)
C4—C5—H5	119.1	Cl3—Sb1—Cl5	166.17 (3)
C5—C6—C7	117.6 (3)	O1—Sb1—Cl6	78.52 (6)
C5—C6—H6	121.2	Cl4—Sb1—Cl6	166.56 (3)
C7—C6—H6	121.2	Cl3—Sb1—Cl6	92.87 (2)
C6—C7—C2	121.5 (3)	Cl5—Sb1—Cl6	82.88 (2)
C6—C7—N1	128.1 (3)	O1—Sb2—Cl1	91.07 (6)
C2—C7—N1	110.4 (3)	O1—Sb2—Cl2	88.67 (6)
C8—S2—C9	90.54 (14)	Cl1—Sb2—Cl2	91.64 (3)
C8—N2—C14	114.6 (2)	O1—Sb2—Cl5	73.22 (5)
C8—N2—H2N	122.7	Cl1—Sb2—Cl5	93.65 (2)
C14—N2—H2N	122.7	Cl2—Sb2—Cl5	161.21 (2)
N2—C8—S2	114.0 (2)	O1—Sb2—Cl6	69.00 (6)
N2—C8—H8	123	Cl1—Sb2—Cl6	158.15 (3)
S2—C8—H8	123	Cl2—Sb2—Cl6	96.56 (2)
C10—C9—C14	120.0 (2)	Cl5—Sb2—Cl6	72.59 (2)
C10—C9—S2	130.0 (2)	Sb1—Cl5—Sb2	72.175 (18)
C14—C9—S2	110.0 (2)	Sb1—O1—Sb2	123.56 (9)
C11—C10—C9	117.5 (3)	Sb1—Cl6—Sb2	65.814 (16)
C11—C10—H10	121.2
C7—N1—C1—S1	−0.1 (4)	C8—N2—C14—C9	−1.1 (3)
C2—S1—C1—N1	0.8 (3)	C10—C9—C14—C13	1.2 (4)
C1—S1—C2—C7	−1.2 (2)	S2—C9—C14—C13	−178.9 (2)
C1—S1—C2—C3	178.1 (3)	C10—C9—C14—N2	−178.8 (2)
C7—C2—C3—C4	−0.2 (4)	S2—C9—C14—N2	1.1 (3)
S1—C2—C3—C4	−179.4 (2)	O1—Sb1—Cl5—Sb2	−17.75 (6)
C2—C3—C4—C5	−0.6 (5)	Cl4—Sb1—Cl5—Sb2	−106.31 (2)
C3—C4—C5—C6	1.0 (5)	Cl3—Sb1—Cl5—Sb2	−11.07 (11)
C4—C5—C6—C7	−0.5 (4)	Cl6—Sb1—Cl5—Sb2	61.70 (2)
C5—C6—C7—C2	−0.3 (4)	O1—Sb2—Cl5—Sb1	18.27 (6)
C5—C6—C7—N1	178.1 (3)	Cl1—Sb2—Cl5—Sb1	108.29 (3)
C3—C2—C7—C6	0.7 (4)	Cl2—Sb2—Cl5—Sb1	2.25 (9)
S1—C2—C7—C6	180.0 (2)	Cl6—Sb2—Cl5—Sb1	−54.403 (18)
C3—C2—C7—N1	−178.0 (3)	Cl4—Sb1—O1—Sb2	124.26 (11)
S1—C2—C7—N1	1.3 (3)	Cl3—Sb1—O1—Sb2	−145.35 (12)
C1—N1—C7—C6	−179.4 (3)	Cl5—Sb1—O1—Sb2	33.05 (11)
C1—N1—C7—C2	−0.8 (4)	Cl6—Sb1—O1—Sb2	−51.47 (11)
C14—N2—C8—S2	0.6 (3)	Cl1—Sb2—O1—Sb1	−124.01 (11)
C9—S2—C8—N2	0.1 (2)	Cl2—Sb2—O1—Sb1	144.37 (12)
C8—S2—C9—C10	179.2 (3)	Cl5—Sb2—O1—Sb1	−30.53 (10)
C8—S2—C9—C14	−0.7 (2)	Cl6—Sb2—O1—Sb1	46.83 (10)
C14—C9—C10—C11	−0.6 (4)	O1—Sb1—Cl6—Sb2	24.73 (6)
S2—C9—C10—C11	179.5 (2)	Cl4—Sb1—Cl6—Sb2	6.05 (11)
C9—C10—C11—C12	−0.1 (4)	Cl3—Sb1—Cl6—Sb2	109.41 (2)
C10—C11—C12—C13	0.4 (5)	Cl5—Sb1—Cl6—Sb2	−57.378 (18)
C11—C12—C13—C14	0.2 (5)	O1—Sb2—Cl6—Sb1	−25.97 (6)
C12—C13—C14—N2	179.1 (3)	Cl1—Sb2—Cl6—Sb1	−0.64 (7)
C12—C13—C14—C9	−1.0 (4)	Cl2—Sb2—Cl6—Sb1	−112.00 (2)
C8—N2—C14—C13	178.9 (3)	Cl5—Sb2—Cl6—Sb1	52.283 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···Cl6^i	0.86	2.37	3.200 (3)	162
N2—H2N···Cl6^ii	0.86	2.35	3.145 (3)	153
C1—H1···O1	0.93	2.27	3.152 (4)	159
C8—H8···Cl5^iii	0.93	2.72	3.327 (3)	124
C10—H10···Cl3^iv	0.93	2.78	3.612 (3)	150
C13—H13···Cl2^ii	0.93	2.76	3.524 (3)	140

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