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The crystal structures of the two isomers bis­(1-phenyl­ethyl­ammonium) hexa­chloridostannate(IV) and bis­(2-phenyl­ethyl­ammonium) hexa­chloridostannate(IV), both (C8H12N)2[SnCl6], exhibit alternating organic and inorganic layers, which inter­act via N—H...Cl hydrogen bonding. The inorganic layer contains an extended two-dimensional hydrogen-bonded sheet. The Sn atom in the 1-phenylethyl­ammonium salt lies on an inversion centre.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107004970/bm3024sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107004970/bm3024Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270107004970/bm3024IIsup3.hkl
Contains datablock II

CCDC references: 641786; 641787

Comment top

A significant number of organic/inorganic compounds of the formula (R–NH3)2SnX4 (where X is F, Cl, Br or I) have previously been investigated structurally because of their interesting magnetic and optical properties (Mitzi et al., 1998; Raptopoulou et al., 2002). In contrast, compounds of the formula (R–NH3)2SnX6 have not been studied extensively. The crystal structures of only four primary n-alkylammonium hexachlorotin(IV) compounds – with organic chain lengths ranging from one to six (Kitahama et al., 1979; Knop et al., 1983; Eulleuch et al., 1996; Lemmerer et al., 2007) – and two primary arylammonium hexachlorotin(IV) organic–inorganic hybrid compounds (Rademeyer, 2004a,b) have been reported in the literature.

In the present investigation, two novel crystal structures of organic–inorganic hybrid materials are reported, namely bis(1-phenylethylammonium) hexachloridostannate(IV), (I), and bis(2-phenylethylammonium) hexachloridostannate(IV), (II). A comparison of the structures reveals the effect of a slight change in the cation and the introduction of a chiral cation on the packing of molecular ions in the crystal structures.

The structures of (I) and (II), in which the cations are structural isomers, can be compared with that of bis(benzylammonium) hexachloridostannate(IV), (III) (Rademeyer, 2004a), as they form a logical series; relative to (III), (I) has an additional methyl group on the C atom adjacent to the ammonium group, while the arylammonium chain in (II) is longer by one methylene group than that in (III).

The molecular geometry and atomic numbering schemes employed for (I) and (II) are illustrated in Fig. 1. In the solid state, (I) and (II) self-assemble into structures consisting of alternating organic layers, consisting of the ammonium cations bis(1-phenylethylammonium) [for (I)] and bis(2-phenylethylammonium) hexachloridostannate(IV) [(II)], and inorganic layers, made up of isolated SnCl6 octahedra. The layers stack along the a axis in (I) and along the b axis in (II), as illustrated in Figs. 2 and 3, respectively. In both structures, the inorganic layer and organic layer interact via hydrogen bonds to form a two-dimensional network parallel to the bc plane in (I) and parallel to the ac plane in (II).

The inorganic part of the asymmetric unit of (I) contains an Sn atom on a centre of inversion at (1/2, 0, 1/2) and three Cl atoms in general positions. The inversion centre generates an SnCl6 octahedron, in which the three unique Sn—Cl bond lengths are 2.4270 (11), 2.4310 (12) and 2.4557 (12) Å (see Table 3), and the cis Cl—Sn—Cl bond angles range from 89.56 (4)° to 90.44 (4)°, indicating only slight distortion from ideal octahedral geometry. Each unit cell contains one complete inorganic layer [mean plane equation: 12.217 (2) x = 6.109 (1) Å; symmetry operators of atoms used: Sn1 (x, y, z), (x, 1 + y, z), (1 - x, 1/2 + y, 1/2 - z), Sn1 (1 - x, 1/2 + y, 3/2 - z)] and successive layers are separated by the unit cell repeat a of 12.243 (2) Å.

The organic layer of (I) has one independent 1-phenylethylammonium cation on a general position. The aromatic ring plane [C3–C8; mean plane equation: 8.68 (3) x - 2.75 (2) y - 8.75 (6) z = 2.94 (4) Å] is inclined at an angle of 48.0 (2)° to the plane of the inorganic layer. Within the organic layers, adjacent aromatic rings are separated by a centroid-to-centroid distance of 5.268 Å, clearly far too large to be considered as a π-stacking interaction.

The hydrogen-bonding interactions linking the organic layer and the inorganic layer involve the three H atoms on the ammonium group. There are two simple and one bifurcated hydrogen bonds between one cation and three different SnCl6 octahedra (Fig. 4 and Table 1).

The asymmetric unit of (II) comprises two crystallographically independent 2-phenylethylammonium cations, labelled cat1 (containing atom N1) and cat2 (containing atom N2), and one octahedral [SnCl6]2- anion, the atoms of which lie in general positions. Each unit cell contains two complete inorganic layers [mean plane equation: 25.45 (1) y - 1.660 (2) z = 11.893 (5) Å; symmetry operators of atoms used: Sn1 (x, y, z), (1 + x, y, z), (-x, 1 - y, 1 - z), (1 - x, 1 - y, 1 - z)]. The Sn—Cl bond lengths range from 2.4118 (16) to 2.4342 (17) Å (see Table 3) and the cis Cl—Sn—Cl angles from 88.68 (6)° to 91.61 (7)° indicating small distortions from ideal octahedral geometry.

Within the organic layer of (II), the cations pack in an interdigitated fashion. The planes of the aromatic rings of the two cations are tilted by 80.6 (2)° [for C3A–C8A; mean plane equation: 6.66 (1) x - 0.06 (9) y + 5.03 (4) z = 9.90 (8) Å] and 86.5 (2)° [for C3B–C8B; mean plane equation: 6.59 (1) x + 2.72 (8) y - 5.13 (3) z = 2.20 (6) Å] relative to the inorganic layer plane, and by 50.6 (2)° relative to one another. Weak C—H···π interactions are present in this layer, with atom C4A interacting with the centroid Cg2 of the aromatic group C3B–C8B (symmetry operator: x, 3/2 - y, -1/2 + z) through atom H4A (CH···Cg2 = 2.82 Å and C—H···Cg2 = 133°), and atom C7A interacting with the centroid Cg2 of another ring (symmetry operator: -1 + x, y, -1 + z) through atom H7A (CH···Cg = 2.83 Å and C—H···Cg2 = 136°; see Fig. 5).

In (II), the two crystallographically independent cations display the same hydrogen-bonding interactions with the [SnCl6]2- anions. Atoms N1 and N2 interact with three anions each through three simple hydrogen bonds (Fig. 6). The hydrogen bond N1—H1C···Cl2 has a hydrogen–acceptor distance of 2.92 Å and can be classified as a short contact.

A notable difference between the three structures lies in the volume of the unit cell, which is approximately doubled in (II) and (III) compared with (I). The organic cations in (I) and (III) have approximately the same length, but because the cations are non-interdigitated in (I) and interdigitated in (III), the interlayer spacing of (III) is shorter than that of (I) (see the values in Table 1). Although the cation in (II) is longer than that in (I), the two interlayer spacings are similar as a result of the interdigitation of the organic layer of (II), and the fact that the rings are tilted at different angles to the inorganic layer, thus compensating for the different packing arrangements of the organic layer.

In (I), neigbouring cations participate in hydrogen bonding with different inorganic layers, thus alternating in orientation, as shown in Fig. 2. However, in (II) pairs of cations point in the same direction, and neighbouring pairs alternate in orientation (Fig. 3), and the same is observed for (III). In all three structures, the hydrogen bonds give rise to a complex hydrogen-bonded network extending in two-dimensions. The packing efficiency of (I) is slightly lower than that of (II) and (III) (Table 1), possibly because the sterically hindering methyl group prevents more efficient packing.

In summary, slight changes to the cation cause subtle differences in the structures of compounds (I), (II) and (III), involving changes in interdigitation and cation orientation. Overall, however, the structures are still very similar, indicating that self-assembly in the hydrophobic and hydrophilic layers and hydrogen-bond formation are the major driving forces that dictate the packing.

Related literature top

For related literature, see: Eulleuch et al. (1996); Kitahama (1979); Knop et al. (1983); Lemmerer et al. (2007); Mitzi et al. (1998); Rademeyer (2004a, 2004b); Raptopoulou et al. (2002).

Experimental top

For the preparation of (I), 1-phenylethylamine (0.068 g, 0.561 mmol) was combined with tin(II) chloride (0.054 g, 0.259 mmol) and dissolved in concentrated HCl (5 ml, 0.057 mol, 33%, Aldrich). The resulting solution was left open to the atmosphere and crystals grew by slow evaporation. A colourless, plate-like crystal was selected for the X-ray diffraction study. 2-Phenylethylammonium chloride was prepared by the dropwise addition of excess concentrated HCl (4.82 ml, 0.059 mol, 37%, Aldrich) to a solution of 2-phenylethylamine (2.4 ml, 0.020 mol, 99%, Aldrich) in chloroform (10 ml, 99%, Saarchem). The resulting precipitate was filtered off and left to dry. Crystals of (II) were grown by slow evaporation from an aqueous solution of stoichiometric amounts (1:2) of tin(II) chloride (0.065 g, 0.340 mmol) and 2-phenylethylammonium chloride (0.107 g, 0.679 mmol) to total dryness. A colourless crystal was selected for the X-ray diffraction study.

Refinement top

H atoms were placed geometrically and refined in idealized positions in the riding-model approximation, with C—H = 0.93 (ArH), 0.98 (CH), 0.97 (CH2) and 0.96 Å (CH3) and N—H = 0.89 Å; Uiso(H) = 1.5Ueq(N), 1.5Ueq(C) for methyl H atoms and 1.2Ueq(C) for other H atoms. The highest residual peaks in the final ΔF syntheses lie 1.07 Å from Cl2 in (I) and 1.67 Å from Cl5 in (II). Location of deepest hole for (II)?

Computing details top

Data collection: SMART-NT (Bruker, 1998) for (I); CrysAlis CCD (Oxford Diffraction 2003) for (II). Cell refinement: SAINT-Plus (Bruker, 1999) for (I); CrysAlis CCD for (II). Data reduction: SAINT-Plus for (I); CrysAlis RED (Oxford Diffraction, 2003) for (II). For both compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and Diamond (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. Views of the structures of (a) (I) and (b) (II), showing the atom-numbering schemes. Displacement ellipsoids are shown at the 50% probability level. [Symmetry code: (ii) -x + 1, -y + 1, -z + 1.]
[Figure 2] Fig. 2. Packing diagram of (I), viewed along the b axis. The 1-phenylethylammonium cations are non-interdigitated.
[Figure 3] Fig. 3. Packing diagram of (II) viewed along the a axis. The 2-phenylethylammonium cations are interdigitated.
[Figure 4] Fig. 4. Magnified view of the hydrogen bonding in (I) between the 1-phenylethylammonium cation and three [SnCl6]2- anions. [Symmetry codes: (i) x, -y + 1/2, z - 1/2; (ii) -x + 1, -y + 1, -z + 1.]
[Figure 5] Fig. 5. The C—H···π interactions in (II) between cat1 and cat2. [Symmetry codes: (v) x, -y + 3/2, z - 1/2; (vi) x - 1, y, z - 1.]
[Figure 6] Fig. 6. A magnified view of the hydrogen bonding in (II) between the two 2-phenylethylammonium cations and five [SnCl6]2- anions. [Symmetry codes: (i) x + 1, y, z; (ii) -x + 1, -y + 1, -z + 1; (iii) -x, -y + 1, -z + 1; (iv) -x + 1, -y + 1, -z + 2.]
(I) Bis(1-phenylethylammonium) hexachloridostannate(IV) top
Crystal data top
(C8H12N)2[SnCl6]F(000) = 572
Mr = 575.76Dx = 1.597 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 937 reflections
a = 12.243 (2) Åθ = 3.2–28.2°
b = 7.1124 (13) ŵ = 1.74 mm1
c = 13.777 (3) ÅT = 293 K
β = 93.697 (3)°Plate, colourless
V = 1197.2 (4) Å30.48 × 0.28 × 0.13 mm
Z = 2
Data collection top
Bruker APEX II CCD area-detector
diffractometer
1736 reflections with I > 2σ(I)
ω scansRint = 0.067
Absorption correction: integration
(XPREP; Bruker, 1999)
θmax = 25.5°, θmin = 1.7°
Tmin = 0.443, Tmax = 0.821h = 1414
6461 measured reflectionsk = 58
2228 independent reflectionsl = 1616
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.031 w = 1/[σ2(Fo2) + 2.608P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.097(Δ/σ)max = 0.001
S = 1.30Δρmax = 0.96 e Å3
2228 reflectionsΔρmin = 0.50 e Å3
103 parameters
Crystal data top
(C8H12N)2[SnCl6]V = 1197.2 (4) Å3
Mr = 575.76Z = 2
Monoclinic, P21/cMo Kα radiation
a = 12.243 (2) ŵ = 1.74 mm1
b = 7.1124 (13) ÅT = 293 K
c = 13.777 (3) Å0.48 × 0.28 × 0.13 mm
β = 93.697 (3)°
Data collection top
Bruker APEX II CCD area-detector
diffractometer
2228 independent reflections
Absorption correction: integration
(XPREP; Bruker, 1999)
1736 reflections with I > 2σ(I)
Tmin = 0.443, Tmax = 0.821Rint = 0.067
6461 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.30Δρmax = 0.96 e Å3
2228 reflectionsΔρmin = 0.50 e Å3
103 parameters
Special details top

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.7645 (5)0.2771 (7)0.2768 (5)0.0612 (14)
H1F0.70520.19750.25330.092*
H1E0.79240.23410.33970.092*
H1D0.82170.27270.23240.092*
C20.7239 (4)0.4772 (6)0.2847 (4)0.0430 (10)
H20.69630.51810.21970.052*
C30.8111 (2)0.6143 (4)0.3215 (2)0.0432 (10)
C40.8496 (3)0.7438 (5)0.2563 (2)0.0631 (15)
H40.81840.74970.1930.076*
C50.9347 (3)0.8645 (5)0.2857 (4)0.082 (2)
H50.96040.95120.24210.098*
C60.9812 (3)0.8557 (6)0.3803 (4)0.096 (3)
H61.03810.93650.40.115*
C70.9427 (3)0.7262 (7)0.4455 (3)0.099 (3)
H70.97380.72030.50880.119*
C80.8576 (3)0.6055 (6)0.4161 (2)0.0738 (18)
H80.83180.51880.45970.089*
N10.6295 (3)0.4797 (6)0.3499 (3)0.0455 (9)
H1A0.57850.39880.32750.068*
H1B0.60120.59480.35080.068*
H1C0.65330.44690.40990.068*
Sn10.500.50.03701 (15)
Cl10.40919 (10)0.28166 (16)0.43644 (9)0.0468 (3)
Cl20.44804 (10)0.07795 (18)0.66444 (8)0.0474 (3)
Cl30.67011 (10)0.17346 (18)0.52875 (9)0.0530 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.068 (4)0.045 (3)0.072 (4)0.005 (3)0.025 (3)0.006 (3)
C20.048 (3)0.047 (3)0.034 (2)0.004 (2)0.0015 (19)0.0019 (19)
C30.034 (2)0.038 (2)0.058 (3)0.0021 (19)0.007 (2)0.000 (2)
C40.048 (3)0.050 (3)0.094 (5)0.003 (2)0.016 (3)0.008 (3)
C50.058 (4)0.046 (3)0.146 (7)0.009 (3)0.034 (4)0.004 (4)
C60.062 (4)0.069 (4)0.159 (9)0.021 (3)0.024 (5)0.048 (5)
C70.080 (5)0.114 (6)0.102 (6)0.022 (5)0.007 (4)0.034 (5)
C80.069 (4)0.086 (5)0.065 (4)0.021 (3)0.005 (3)0.003 (3)
N10.039 (2)0.047 (2)0.051 (2)0.0008 (17)0.0062 (18)0.0026 (18)
Sn10.0422 (3)0.0345 (2)0.0344 (2)0.00069 (18)0.00287 (17)0.00158 (17)
Cl10.0517 (6)0.0403 (6)0.0485 (6)0.0066 (5)0.0042 (5)0.0064 (5)
Cl20.0544 (7)0.0528 (7)0.0352 (6)0.0057 (5)0.0053 (5)0.0008 (5)
Cl30.0525 (7)0.0564 (7)0.0491 (7)0.0153 (6)0.0049 (5)0.0103 (6)
Geometric parameters (Å, º) top
C1—C21.514 (7)C5—H50.93
C1—H1F0.96C6—C71.39
C1—H1E0.96C6—H60.93
C1—H1D0.96C7—C81.39
C2—N11.508 (6)C7—H70.93
C2—C31.509 (5)C8—H80.93
C2—H20.98N1—H1A0.89
C3—C41.39N1—H1B0.89
C3—C81.39N1—H1C0.89
C4—C51.39Sn1—Cl12.4270 (11)
C4—H40.93Sn1—Cl32.4310 (12)
C5—C61.39Sn1—Cl22.4557 (12)
C2—C1—H1F109.5C4—C5—H5120
C2—C1—H1E109.5C5—C6—C7120
H1F—C1—H1E109.5C5—C6—H6120
C2—C1—H1D109.5C7—C6—H6120
H1F—C1—H1D109.5C8—C7—C6120
H1E—C1—H1D109.5C8—C7—H7120
N1—C2—C3110.2 (4)C6—C7—H7120
N1—C2—C1108.8 (4)C7—C8—C3120
C3—C2—C1113.8 (4)C7—C8—H8120
N1—C2—H2108C3—C8—H8120
C3—C2—H2108C2—N1—H1A109.5
C1—C2—H2108C2—N1—H1B109.5
C4—C3—C8120H1A—N1—H1B109.5
C4—C3—C2118.3 (3)C2—N1—H1C109.5
C8—C3—C2121.6 (3)H1A—N1—H1C109.5
C5—C4—C3120H1B—N1—H1C109.5
C5—C4—H4120Cl1—Sn1—Cl290.38 (4)
C3—C4—H4120Cl1—Sn1—Cl390.44 (4)
C6—C5—C4120Cl2—Sn1—Cl390.30 (4)
C6—C5—H5120
N1—C2—C3—C4128.8 (3)C3—C4—C5—C60
C1—C2—C3—C4108.7 (4)C4—C5—C6—C70
N1—C2—C3—C855.3 (4)C5—C6—C7—C80
C1—C2—C3—C867.1 (5)C6—C7—C8—C30
C8—C3—C4—C50C4—C3—C8—C70
C2—C3—C4—C5175.9 (3)C2—C3—C8—C7175.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl2i0.892.683.302 (4)128
N1—H1A···Cl10.892.763.331 (4)123
N1—H1B···Cl2ii0.892.413.289 (4)170
N1—H1C···Cl30.892.543.302 (5)144
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1, z+1.
(II) Bis(2-phenylethylammonium) hexachloridostannate(IV) top
Crystal data top
(C8H12N)2[SnCl6]F(000) = 1144
Mr = 575.76Dx = 1.695 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 763 reflections
a = 7.335 (3) Åθ = 2.4–31.3°
b = 25.695 (4) ŵ = 1.85 mm1
c = 11.974 (2) ÅT = 293 K
β = 90.03 (2)°Plate, colourless
V = 2256.8 (11) Å30.2 × 0.2 × 0.15 mm
Z = 4
Data collection top
Oxford Excalibur2 CCD area detector
diffractometer
3144 reflections with I > 2σ(I)
ω–2θ scans ##AUTHOR: Please check diffractometer and scan type.Rint = 0.038
Absorption correction: multi-scan
(WinGX; Farrugia, 1999)
θmax = 25.5°, θmin = 4.2°
Tmin = 0.709, Tmax = 0.753h = 58
14565 measured reflectionsk = 3131
4159 independent reflectionsl = 1414
Refinement top
Refinement on F2150 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.050 w = 1/[σ2(Fo2) + (0.049P)2 + 6.342P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.122(Δ/σ)max = 0.008
S = 1.05Δρmax = 1.01 e Å3
4159 reflectionsΔρmin = 1.00 e Å3
202 parameters
Crystal data top
(C8H12N)2[SnCl6]V = 2256.8 (11) Å3
Mr = 575.76Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.335 (3) ŵ = 1.85 mm1
b = 25.695 (4) ÅT = 293 K
c = 11.974 (2) Å0.2 × 0.2 × 0.15 mm
β = 90.03 (2)°
Data collection top
Oxford Excalibur2 CCD area detector
diffractometer
4159 independent reflections
Absorption correction: multi-scan
(WinGX; Farrugia, 1999)
3144 reflections with I > 2σ(I)
Tmin = 0.709, Tmax = 0.753Rint = 0.038
14565 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050150 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.05Δρmax = 1.01 e Å3
4159 reflectionsΔρmin = 1.00 e Å3
202 parameters
Special details top

Experimental. absorption corrections were made in the WinGX suite of programs (Blessing, 1995).

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C1A0.2106 (10)0.6086 (3)0.3904 (6)0.0605 (18)
H1A10.21660.62560.46260.073*
H1A20.08590.6110.36390.073*
C2A0.3343 (11)0.6371 (3)0.3094 (7)0.075 (2)
H2A10.45720.63770.33940.09*
H2A20.33750.61820.23920.09*
C3A0.2734 (6)0.69113 (14)0.2883 (4)0.0560 (15)
C4A0.3153 (6)0.73071 (19)0.3631 (3)0.0579 (16)
H4A0.37120.72280.43080.069*
C5A0.2737 (7)0.78205 (17)0.3369 (5)0.0690 (18)
H5A0.30180.80850.3870.083*
C6A0.1901 (7)0.79381 (17)0.2358 (5)0.080 (2)
H6A0.16230.82820.21820.095*
C7A0.1482 (7)0.7542 (2)0.1609 (4)0.077 (2)
H7A0.09230.76210.09330.093*
C8A0.1898 (7)0.7029 (2)0.1872 (4)0.0720 (18)
H8A0.16170.67640.13710.086*
N10.2597 (8)0.5529 (2)0.4041 (5)0.0558 (15)
H1A0.18350.5380.45230.084*
H1B0.37320.55050.42980.084*
H1C0.25180.53690.33840.084*
C1B0.7207 (17)0.6267 (3)0.9090 (8)0.103 (3)
H1B10.59280.63280.89320.124*
H1B20.79020.64050.84670.124*
C2B0.7709 (19)0.6569 (4)1.0121 (9)0.121 (3)
H2B10.69890.64451.07450.146*
H2B20.89840.65091.02940.146*
C3B0.7403 (8)0.71276 (15)0.9977 (5)0.081 (2)
C4B0.6669 (8)0.7335 (2)1.0950 (4)0.079 (2)
H4B0.62450.71151.15090.095*
C5B0.6570 (7)0.7871 (2)1.1088 (4)0.0745 (19)
H5B0.60790.8011.1740.089*
C6B0.7204 (7)0.82003 (15)1.0253 (5)0.0720 (19)
H6B0.71380.85591.03460.086*
C7B0.7938 (7)0.7993 (2)0.9280 (4)0.0676 (18)
H7B0.83620.82130.87210.081*
C8B0.8037 (7)0.7457 (2)0.9142 (4)0.0695 (18)
H8B0.85280.73180.8490.083*
N20.7513 (8)0.5700 (2)0.9146 (5)0.0540 (15)
H2A0.71430.55530.85120.081*
H2B0.68860.55670.97150.081*
H2C0.86960.56370.92450.081*
Sn10.24446 (5)0.516656 (16)0.75527 (3)0.03282 (15)
Cl10.4767 (2)0.56867 (7)0.66429 (14)0.0504 (4)
Cl20.0129 (2)0.46313 (7)0.84425 (14)0.0481 (4)
Cl30.4835 (2)0.46809 (6)0.85029 (13)0.0448 (4)
Cl40.0030 (2)0.56365 (7)0.66037 (14)0.0489 (4)
Cl50.2577 (2)0.45597 (7)0.59993 (13)0.0481 (4)
Cl60.2341 (2)0.57647 (7)0.91037 (13)0.0468 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.065 (4)0.052 (3)0.064 (4)0.008 (3)0.011 (4)0.010 (3)
C2A0.068 (4)0.054 (3)0.105 (5)0.002 (3)0.027 (4)0.010 (3)
C3A0.045 (3)0.049 (3)0.074 (4)0.003 (3)0.015 (3)0.003 (3)
C4A0.046 (4)0.056 (3)0.071 (4)0.004 (3)0.004 (3)0.002 (3)
C5A0.057 (4)0.050 (3)0.100 (5)0.000 (3)0.008 (4)0.005 (4)
C6A0.063 (4)0.070 (4)0.105 (5)0.007 (4)0.017 (4)0.029 (3)
C7A0.054 (4)0.104 (5)0.075 (4)0.005 (4)0.004 (4)0.027 (3)
C8A0.059 (4)0.086 (4)0.070 (4)0.004 (4)0.005 (3)0.005 (3)
N10.067 (4)0.044 (3)0.056 (4)0.005 (3)0.003 (3)0.001 (3)
C1B0.136 (7)0.050 (4)0.124 (7)0.004 (5)0.015 (6)0.011 (4)
C2B0.169 (7)0.064 (4)0.132 (6)0.001 (5)0.024 (6)0.010 (4)
C3B0.098 (5)0.052 (3)0.093 (5)0.001 (4)0.002 (4)0.008 (3)
C4B0.075 (5)0.085 (4)0.077 (4)0.014 (4)0.003 (4)0.005 (4)
C5B0.062 (4)0.091 (4)0.071 (4)0.010 (4)0.002 (4)0.025 (4)
C6B0.061 (4)0.060 (4)0.095 (5)0.005 (4)0.016 (4)0.020 (3)
C7B0.051 (4)0.067 (4)0.085 (4)0.007 (4)0.001 (3)0.009 (3)
C8B0.061 (4)0.071 (4)0.077 (4)0.007 (4)0.010 (4)0.017 (3)
N20.054 (3)0.050 (3)0.058 (4)0.002 (3)0.001 (3)0.002 (3)
Sn10.0291 (2)0.0391 (2)0.0303 (2)0.00212 (19)0.00026 (15)0.00088 (18)
Cl10.0431 (9)0.0618 (11)0.0462 (9)0.0168 (8)0.0086 (7)0.0063 (8)
Cl20.0411 (9)0.0526 (10)0.0506 (10)0.0120 (8)0.0075 (7)0.0093 (8)
Cl30.0401 (8)0.0473 (10)0.0469 (9)0.0081 (7)0.0103 (7)0.0022 (7)
Cl40.0403 (9)0.0571 (11)0.0493 (10)0.0072 (8)0.0114 (7)0.0090 (8)
Cl50.0563 (10)0.0502 (10)0.0379 (8)0.0030 (8)0.0003 (7)0.0128 (7)
Cl60.0546 (10)0.0503 (10)0.0356 (8)0.0001 (8)0.0014 (7)0.0087 (7)
Geometric parameters (Å, º) top
C1A—N11.485 (8)C1B—H1B20.97
C1A—C2A1.517 (11)C2B—C3B1.462 (11)
C1A—H1A10.97C2B—H2B10.97
C1A—H1A20.97C2B—H2B20.97
C2A—C3A1.481 (8)C3B—C4B1.39
C2A—H2A10.97C3B—C8B1.39
C2A—H2A20.97C4B—C5B1.39
C3A—C4A1.39C4B—H4B0.93
C3A—C8A1.39C5B—C6B1.39
C4A—C5A1.39C5B—H5B0.93
C4A—H4A0.93C6B—C7B1.39
C5A—C6A1.39C6B—H6B0.93
C5A—H5A0.93C7B—C8B1.39
C6A—C7A1.39C7B—H7B0.93
C6A—H6A0.93C8B—H8B0.93
C7A—C8A1.39N2—H2A0.89
C7A—H7A0.93N2—H2B0.89
C8A—H8A0.93N2—H2C0.89
N1—H1A0.89Sn1—Cl12.4244 (17)
N1—H1B0.89Sn1—Cl22.4316 (16)
N1—H1C0.89Sn1—Cl32.4342 (17)
C1B—N21.477 (9)Sn1—Cl42.4257 (17)
C1B—C2B1.503 (11)Sn1—Cl52.4291 (16)
C1B—H1B10.97Sn1—Cl62.4118 (16)
N1—C1A—C2A113.0 (6)C1B—C2B—H2B1109.3
N1—C1A—H1A1109C3B—C2B—H2B2109.2
C2A—C1A—H1A1109C1B—C2B—H2B2109.2
N1—C1A—H1A2109H2B1—C2B—H2B2107.9
C2A—C1A—H1A2109C4B—C3B—C8B120
H1A1—C1A—H1A2107.8C4B—C3B—C2B109.7 (6)
C3A—C2A—C1A112.4 (6)C8B—C3B—C2B129.0 (6)
C3A—C2A—H2A1109.1C3B—C4B—C5B120
C1A—C2A—H2A1109.1C3B—C4B—H4B120
C3A—C2A—H2A2109.1C5B—C4B—H4B120
C1A—C2A—H2A2109.1C6B—C5B—C4B120
H2A1—C2A—H2A2107.9C6B—C5B—H5B120
C4A—C3A—C8A120C4B—C5B—H5B120
C4A—C3A—C2A120.6 (5)C5B—C6B—C7B120
C8A—C3A—C2A119.0 (5)C5B—C6B—H6B120
C3A—C4A—C5A120C7B—C6B—H6B120
C3A—C4A—H4A120C8B—C7B—C6B120
C5A—C4A—H4A120C8B—C7B—H7B120
C6A—C5A—C4A120C6B—C7B—H7B120
C6A—C5A—H5A120C7B—C8B—C3B120
C4A—C5A—H5A120C7B—C8B—H8B120
C7A—C6A—C5A120C3B—C8B—H8B120
C7A—C6A—H6A120C1B—N2—H2A109.5
C5A—C6A—H6A120C1B—N2—H2B109.5
C6A—C7A—C8A120H2A—N2—H2B109.5
C6A—C7A—H7A120C1B—N2—H2C109.5
C8A—C7A—H7A120H2A—N2—H2C109.5
C7A—C8A—C3A120H2B—N2—H2C109.5
C7A—C8A—H8A120Cl1—Sn1—Cl2178.93 (6)
C3A—C8A—H8A120Cl1—Sn1—Cl389.22 (7)
C1A—N1—H1A109.5Cl1—Sn1—Cl491.61 (7)
C1A—N1—H1B109.5Cl1—Sn1—Cl588.93 (6)
H1A—N1—H1B109.5Cl1—Sn1—Cl690.98 (6)
C1A—N1—H1C109.5Cl2—Sn1—Cl390.48 (6)
H1A—N1—H1C109.5Cl2—Sn1—Cl488.68 (6)
H1B—N1—H1C109.5Cl2—Sn1—Cl590.04 (6)
N2—C1B—C2B115.8 (8)Cl2—Sn1—Cl690.05 (6)
N2—C1B—H1B1108.3Cl3—Sn1—Cl4178.98 (6)
C2B—C1B—H1B1108.3Cl3—Sn1—Cl589.99 (6)
N2—C1B—H1B2108.3Cl3—Sn1—Cl689.41 (6)
C2B—C1B—H1B2108.3Cl4—Sn1—Cl589.44 (6)
H1B1—C1B—H1B2107.4Cl4—Sn1—Cl691.16 (6)
C3B—C2B—C1B111.9 (7)Cl5—Sn1—Cl6179.39 (6)
C3B—C2B—H2B1109.2
N1—C1A—C2A—C3A174.6 (6)N2—C1B—C2B—C3B178.6 (9)
C1A—C2A—C3A—C4A81.2 (8)C1B—C2B—C3B—C4B139.6 (9)
C1A—C2A—C3A—C8A105.3 (7)C1B—C2B—C3B—C8B53.5 (14)
C8A—C3A—C4A—C5A0C8B—C3B—C4B—C5B0
C2A—C3A—C4A—C5A173.4 (5)C2B—C3B—C4B—C5B168.3 (7)
C3A—C4A—C5A—C6A0C3B—C4B—C5B—C6B0
C4A—C5A—C6A—C7A0C4B—C5B—C6B—C7B0
C5A—C6A—C7A—C8A0C5B—C6B—C7B—C8B0
C6A—C7A—C8A—C3A0C6B—C7B—C8B—C3B0
C4A—C3A—C8A—C7A0C4B—C3B—C8B—C7B0
C2A—C3A—C8A—C7A173.5 (5)C2B—C3B—C8B—C7B165.7 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl50.892.803.421 (6)128
N1—H1B···Cl5i0.892.743.548 (6)152
N1—H1C···Cl2ii0.892.923.606 (6)135
N2—H2A···Cl30.892.813.362 (6)122
N2—H2B···Cl3iii0.892.563.443 (6)171
N2—H2C···Cl6iv0.892.703.546 (6)159
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1, z+2; (iv) x+1, y, z.

Experimental details

(I)(II)
Crystal data
Chemical formula(C8H12N)2[SnCl6](C8H12N)2[SnCl6]
Mr575.76575.76
Crystal system, space groupMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)293293
a, b, c (Å)12.243 (2), 7.1124 (13), 13.777 (3)7.335 (3), 25.695 (4), 11.974 (2)
β (°) 93.697 (3) 90.03 (2)
V3)1197.2 (4)2256.8 (11)
Z24
Radiation typeMo KαMo Kα
µ (mm1)1.741.85
Crystal size (mm)0.48 × 0.28 × 0.130.2 × 0.2 × 0.15
Data collection
DiffractometerBruker APEX II CCD area-detector
diffractometer
Oxford Excalibur2 CCD area detector
diffractometer
Absorption correctionIntegration
(XPREP; Bruker, 1999)
Multi-scan
(WinGX; Farrugia, 1999)
Tmin, Tmax0.443, 0.8210.709, 0.753
No. of measured, independent and
observed [I > 2σ(I)] reflections
6461, 2228, 1736 14565, 4159, 3144
Rint0.0670.038
(sin θ/λ)max1)0.6060.606
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.097, 1.30 0.050, 0.122, 1.05
No. of reflections22284159
No. of parameters103202
No. of restraints0150
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.96, 0.501.01, 1.00

Computer programs: SMART-NT (Bruker, 1998), CrysAlis CCD (Oxford Diffraction 2003), SAINT-Plus (Bruker, 1999), CrysAlis CCD, SAINT-Plus, CrysAlis RED (Oxford Diffraction, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and Diamond (Brandenburg, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl2i0.892.683.302 (4)128
N1—H1A···Cl10.892.763.331 (4)123
N1—H1B···Cl2ii0.892.413.289 (4)170
N1—H1C···Cl30.892.543.302 (5)144
Symmetry codes: (i) x, y+1/2, z1/2; (ii) x+1, y+1, z+1.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···Cl50.892.803.421 (6)128
N1—H1B···Cl5i0.892.743.548 (6)152
N1—H1C···Cl2ii0.892.923.606 (6)135
N2—H2A···Cl30.892.813.362 (6)122
N2—H2B···Cl3iii0.892.563.443 (6)171
N2—H2C···Cl6iv0.892.703.546 (6)159
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y+1, z+1; (iii) x+1, y+1, z+2; (iv) x+1, y, z.
Comparative geometric parameters (Å ,° ) in (I), (II) and (III) that have related aromatic cations. top
Parameter(I)(II)(III)a
Sn1—Cl12.4270 (11)2.4244 (16)2.4242 (12)
Sn1—Cl22.4557 (12)2.4316 (16)2.4590 (12)
Sn1—Cl32.4310 (11)2.4342 (16)2.4064 (14)
Sn1—Cl4-2.4257 (16)2.4244 (14)
Sn1—Cl5-2.4291 (16)2.4415 (12)
Sn1—Cl6-2.4118 (16)2.4271 (13)
Interplanar spacing12.243 (2)12.848 (4)11.016 (7)
Packing efficiency0.6480.6890.689
a (C6H5CH2NH3)2[SnCl6] [Rademeyer, 2004a; Cambridge Structural Database (Allen, 2002) refcode INIXOS].
 

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