research communications
catena-Poly[bis(1,3-benzothiazol-3-ium) [[dichloridoantimonate(III)]-di-μ-chlorido-μ-oxido-[chloridoantimonate(III)]-μ-chlorido]]
aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Frères Montouri Constantine, 25000, Algeria, and bDépartement Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, Algeria
*Correspondence e-mail: Bouacida_Sofiane@yahoo.fr
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.
Keywords: crystal structure; organic–inorganic hybrid compound; antimony; hydrogen bonding; π–π stacking.
CCDC reference: 1447413
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.
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)°.
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.
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 . Approximate positions for all H atoms were first obtained from the difference 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, Uiso = 1.2Ueq(C or N).
details are summarized in Table 2Supporting information
CCDC reference: 1447413
10.1107/S2056989016000785/hg5468sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2056989016000785/hg5468Isup2.hkl
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.
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.
Crystal data, data collection and structure
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 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, Uiso = 1.2Ueq(C or N).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).
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.
detailsCrystal data, data collection and structure
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 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, Uiso = 1.2Ueq(C or N).Data collection: APEX2 (Bruker, 2011); cell
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).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). |
(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) Å3 | 0.17 × 0.13 × 0.11 mm |
Z = 4 |
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 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)] = 0.022 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.050 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0186P)2 + 1.5448P] where P = (Fo2 + 2Fc2)/3 |
5344 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.77 e Å−3 |
(C7H6NS)2[Sb2Cl6O] | V = 2326.09 (8) Å3 |
Mr = 744.58 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 10.2826 (2) Å | µ = 3.20 mm−1 |
b = 16.2448 (3) Å | T = 295 K |
c = 14.9849 (3) Å | 0.17 × 0.13 × 0.11 mm |
β = 111.674 (1)° |
Bruker APEXII CCD diffractometer | 5344 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | 4627 reflections with I > 2σ(I) |
Tmin = 0.630, Tmax = 0.746 | Rint = 0.026 |
20349 measured reflections |
R[F2 > 2σ(F2)] = 0.022 | 0 restraints |
wR(F2) = 0.050 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.54 e Å−3 |
5344 reflections | Δρmin = −0.77 e Å−3 |
244 parameters |
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. |
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) |
U11 | U22 | U33 | U12 | U13 | U23 | |
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) |
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) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl6i | 0.86 | 2.37 | 3.200 (3) | 162 |
N2—H2N···Cl6ii | 0.86 | 2.35 | 3.145 (3) | 153 |
C1—H1···O1 | 0.93 | 2.27 | 3.152 (4) | 159 |
C8—H8···Cl5iii | 0.93 | 2.72 | 3.327 (3) | 124 |
C10—H10···Cl3iv | 0.93 | 2.78 | 3.612 (3) | 150 |
C13—H13···Cl2ii | 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. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···Cl6i | 0.8600 | 2.3700 | 3.200 (3) | 162.00 |
N2—H2N···Cl6ii | 0.8600 | 2.3500 | 3.145 (3) | 153.00 |
C1—H1···O1 | 0.9300 | 2.2700 | 3.152 (4) | 159.00 |
C8—H8···Cl5iii | 0.9300 | 2.7200 | 3.327 (3) | 124.00 |
C10—H10···Cl3iv | 0.9300 | 2.7800 | 3.612 (3) | 150.00 |
C13—H13···Cl2ii | 0.9300 | 2.7600 | 3.524 (3) | 140.00 |
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. |
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 (Å3) | 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[F2 > 2σ(F2)], wR(F2), 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 (Bruker, 2011), SAINT (Bruker, 2011), SIR2002 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012) and DIAMOND (Brandenburg & Berndt, 2001), WinGX (Farrugia, 2012).
Acknowledgements
This work is supported by the `Unité de recherche de Chimie de l'Environnement et Moléculaire Structurale', CHEMS, Université de Constantine, Algeria. Thanks are due to MESRS and ATRST (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Thématique de Recherche en Sciences et Technologie – Algérie).
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