Bis(1-phenyl­ethyl­ammonium) hexa­chloridostannate(IV) and bis­(2-phenyl­ethyl­ammonium) hexa­chloridostannate(IV)

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.

S1. Comment

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

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).

S2. Experimental

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.

S3. Refinement

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; U_iso(H) = 1.5U_eq(N), 1.5U_eq(C) for methyl H atoms and 1.2U_eq(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

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

	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.]
	Fig. 2. Packing diagram of (I), viewed along the b axis. The 1-phenylethylammonium cations are non-interdigitated.
	Fig. 3. Packing diagram of (II) viewed along the a axis. The 2-phenylethylammonium cations are interdigitated.
	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.]
	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.]
	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)

Crystal data

(C8H12N)2[SnCl6]	F(000) = 572
Mr = 575.76	Dx = 1.597 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 937 reflections
a = 12.243 (2) Å	θ = 3.2–28.2°
b = 7.1124 (13) Å	µ = 1.74 mm^−1
c = 13.777 (3) Å	T = 293 K
β = 93.697 (3)°	Plate, colourless
V = 1197.2 (4) Å^3	0.48 × 0.28 × 0.13 mm
Z = 2

Data collection

Bruker APEX II CCD area-detector diffractometer	1736 reflections with I > 2σ(I)
ω scans	Rint = 0.067
Absorption correction: integration (XPREP; Bruker, 1999)	θmax = 25.5°, θmin = 1.7°
Tmin = 0.443, Tmax = 0.821	h = −14→14
6461 measured reflections	k = −5→8
2228 independent reflections	l = −16→16

Refinement

Refinement on F^2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.031	w = 1/[σ^2(Fo^2) + 2.608P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.097	(Δ/σ)max = 0.001
S = 1.30	Δρmax = 0.96 e Å^−3
2228 reflections	Δρmin = −0.50 e Å^−3
103 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.7645 (5)	0.2771 (7)	0.2768 (5)	0.0612 (14)
H1F	0.7052	0.1975	0.2533	0.092*
H1E	0.7924	0.2341	0.3397	0.092*
H1D	0.8217	0.2727	0.2324	0.092*
C2	0.7239 (4)	0.4772 (6)	0.2847 (4)	0.0430 (10)
H2	0.6963	0.5181	0.2197	0.052*
C3	0.8111 (2)	0.6143 (4)	0.3215 (2)	0.0432 (10)
C4	0.8496 (3)	0.7438 (5)	0.2563 (2)	0.0631 (15)
H4	0.8184	0.7497	0.193	0.076*
C5	0.9347 (3)	0.8645 (5)	0.2857 (4)	0.082 (2)
H5	0.9604	0.9512	0.2421	0.098*
C6	0.9812 (3)	0.8557 (6)	0.3803 (4)	0.096 (3)
H6	1.0381	0.9365	0.4	0.115*
C7	0.9427 (3)	0.7262 (7)	0.4455 (3)	0.099 (3)
H7	0.9738	0.7203	0.5088	0.119*
C8	0.8576 (3)	0.6055 (6)	0.4161 (2)	0.0738 (18)
H8	0.8318	0.5188	0.4597	0.089*
N1	0.6295 (3)	0.4797 (6)	0.3499 (3)	0.0455 (9)
H1A	0.5785	0.3988	0.3275	0.068*
H1B	0.6012	0.5948	0.3508	0.068*
H1C	0.6533	0.4469	0.4099	0.068*
Sn1	0.5	0	0.5	0.03701 (15)
Cl1	0.40919 (10)	0.28166 (16)	0.43644 (9)	0.0468 (3)
Cl2	0.44804 (10)	0.07795 (18)	0.66444 (8)	0.0474 (3)
Cl3	0.67011 (10)	0.17346 (18)	0.52875 (9)	0.0530 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.068 (4)	0.045 (3)	0.072 (4)	−0.005 (3)	0.025 (3)	−0.006 (3)
C2	0.048 (3)	0.047 (3)	0.034 (2)	−0.004 (2)	−0.0015 (19)	0.0019 (19)
C3	0.034 (2)	0.038 (2)	0.058 (3)	0.0021 (19)	0.007 (2)	0.000 (2)
C4	0.048 (3)	0.050 (3)	0.094 (5)	0.003 (2)	0.016 (3)	0.008 (3)
C5	0.058 (4)	0.046 (3)	0.146 (7)	−0.009 (3)	0.034 (4)	−0.004 (4)
C6	0.062 (4)	0.069 (4)	0.159 (9)	−0.021 (3)	0.024 (5)	−0.048 (5)
C7	0.080 (5)	0.114 (6)	0.102 (6)	−0.022 (5)	−0.007 (4)	−0.034 (5)
C8	0.069 (4)	0.086 (5)	0.065 (4)	−0.021 (3)	−0.005 (3)	−0.003 (3)
N1	0.039 (2)	0.047 (2)	0.051 (2)	−0.0008 (17)	0.0062 (18)	−0.0026 (18)
Sn1	0.0422 (3)	0.0345 (2)	0.0344 (2)	−0.00069 (18)	0.00287 (17)	0.00158 (17)
Cl1	0.0517 (6)	0.0403 (6)	0.0485 (6)	0.0066 (5)	0.0042 (5)	0.0064 (5)
Cl2	0.0544 (7)	0.0528 (7)	0.0352 (6)	0.0057 (5)	0.0053 (5)	−0.0008 (5)
Cl3	0.0525 (7)	0.0564 (7)	0.0491 (7)	−0.0153 (6)	−0.0049 (5)	0.0103 (6)

Geometric parameters (Å, º)

C1—C2	1.514 (7)	C5—H5	0.93
C1—H1F	0.96	C6—C7	1.39
C1—H1E	0.96	C6—H6	0.93
C1—H1D	0.96	C7—C8	1.39
C2—N1	1.508 (6)	C7—H7	0.93
C2—C3	1.509 (5)	C8—H8	0.93
C2—H2	0.98	N1—H1A	0.89
C3—C4	1.39	N1—H1B	0.89
C3—C8	1.39	N1—H1C	0.89
C4—C5	1.39	Sn1—Cl1	2.4270 (11)
C4—H4	0.93	Sn1—Cl3	2.4310 (12)
C5—C6	1.39	Sn1—Cl2	2.4557 (12)
C2—C1—H1F	109.5	C4—C5—H5	120
C2—C1—H1E	109.5	C5—C6—C7	120
H1F—C1—H1E	109.5	C5—C6—H6	120
C2—C1—H1D	109.5	C7—C6—H6	120
H1F—C1—H1D	109.5	C8—C7—C6	120
H1E—C1—H1D	109.5	C8—C7—H7	120
N1—C2—C3	110.2 (4)	C6—C7—H7	120
N1—C2—C1	108.8 (4)	C7—C8—C3	120
C3—C2—C1	113.8 (4)	C7—C8—H8	120
N1—C2—H2	108	C3—C8—H8	120
C3—C2—H2	108	C2—N1—H1A	109.5
C1—C2—H2	108	C2—N1—H1B	109.5
C4—C3—C8	120	H1A—N1—H1B	109.5
C4—C3—C2	118.3 (3)	C2—N1—H1C	109.5
C8—C3—C2	121.6 (3)	H1A—N1—H1C	109.5
C5—C4—C3	120	H1B—N1—H1C	109.5
C5—C4—H4	120	Cl1—Sn1—Cl2	90.38 (4)
C3—C4—H4	120	Cl1—Sn1—Cl3	90.44 (4)
C6—C5—C4	120	Cl2—Sn1—Cl3	90.30 (4)
C6—C5—H5	120
N1—C2—C3—C4	−128.8 (3)	C3—C4—C5—C6	0
C1—C2—C3—C4	108.7 (4)	C4—C5—C6—C7	0
N1—C2—C3—C8	55.3 (4)	C5—C6—C7—C8	0
C1—C2—C3—C8	−67.1 (5)	C6—C7—C8—C3	0
C8—C3—C4—C5	0	C4—C3—C8—C7	0
C2—C3—C4—C5	−175.9 (3)	C2—C3—C8—C7	175.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2^i	0.89	2.68	3.302 (4)	128
N1—H1A···Cl1	0.89	2.76	3.331 (4)	123
N1—H1B···Cl2^ii	0.89	2.41	3.289 (4)	170
N1—H1C···Cl3	0.89	2.54	3.302 (5)	144

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

(II) Bis(2-phenylethylammonium) hexachloridostannate(IV)

Crystal data

(C8H12N)2[SnCl6]	F(000) = 1144
Mr = 575.76	Dx = 1.695 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 763 reflections
a = 7.335 (3) Å	θ = 2.4–31.3°
b = 25.695 (4) Å	µ = 1.85 mm^−1
c = 11.974 (2) Å	T = 293 K
β = 90.03 (2)°	Plate, colourless
V = 2256.8 (11) Å^3	0.2 × 0.2 × 0.15 mm
Z = 4

Data collection

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 = 0.753	h = −5→8
14565 measured reflections	k = −31→31
4159 independent reflections	l = −14→14

Refinement

Refinement on F^2	150 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.050	w = 1/[σ^2(Fo^2) + (0.049P)^2 + 6.342P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.122	(Δ/σ)max = 0.008
S = 1.05	Δρmax = 1.01 e Å^−3
4159 reflections	Δρmin = −1.00 e Å^−3
202 parameters

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1A	0.2106 (10)	0.6086 (3)	0.3904 (6)	0.0605 (18)
H1A1	0.2166	0.6256	0.4626	0.073*
H1A2	0.0859	0.611	0.3639	0.073*
C2A	0.3343 (11)	0.6371 (3)	0.3094 (7)	0.075 (2)
H2A1	0.4572	0.6377	0.3394	0.09*
H2A2	0.3375	0.6182	0.2392	0.09*
C3A	0.2734 (6)	0.69113 (14)	0.2883 (4)	0.0560 (15)
C4A	0.3153 (6)	0.73071 (19)	0.3631 (3)	0.0579 (16)
H4A	0.3712	0.7228	0.4308	0.069*
C5A	0.2737 (7)	0.78205 (17)	0.3369 (5)	0.0690 (18)
H5A	0.3018	0.8085	0.387	0.083*
C6A	0.1901 (7)	0.79381 (17)	0.2358 (5)	0.080 (2)
H6A	0.1623	0.8282	0.2182	0.095*
C7A	0.1482 (7)	0.7542 (2)	0.1609 (4)	0.077 (2)
H7A	0.0923	0.7621	0.0933	0.093*
C8A	0.1898 (7)	0.7029 (2)	0.1872 (4)	0.0720 (18)
H8A	0.1617	0.6764	0.1371	0.086*
N1	0.2597 (8)	0.5529 (2)	0.4041 (5)	0.0558 (15)
H1A	0.1835	0.538	0.4523	0.084*
H1B	0.3732	0.5505	0.4298	0.084*
H1C	0.2518	0.5369	0.3384	0.084*
C1B	0.7207 (17)	0.6267 (3)	0.9090 (8)	0.103 (3)
H1B1	0.5928	0.6328	0.8932	0.124*
H1B2	0.7902	0.6405	0.8467	0.124*
C2B	0.7709 (19)	0.6569 (4)	1.0121 (9)	0.121 (3)
H2B1	0.6989	0.6445	1.0745	0.146*
H2B2	0.8984	0.6509	1.0294	0.146*
C3B	0.7403 (8)	0.71276 (15)	0.9977 (5)	0.081 (2)
C4B	0.6669 (8)	0.7335 (2)	1.0950 (4)	0.079 (2)
H4B	0.6245	0.7115	1.1509	0.095*
C5B	0.6570 (7)	0.7871 (2)	1.1088 (4)	0.0745 (19)
H5B	0.6079	0.801	1.174	0.089*
C6B	0.7204 (7)	0.82003 (15)	1.0253 (5)	0.0720 (19)
H6B	0.7138	0.8559	1.0346	0.086*
C7B	0.7938 (7)	0.7993 (2)	0.9280 (4)	0.0676 (18)
H7B	0.8362	0.8213	0.8721	0.081*
C8B	0.8037 (7)	0.7457 (2)	0.9142 (4)	0.0695 (18)
H8B	0.8528	0.7318	0.849	0.083*
N2	0.7513 (8)	0.5700 (2)	0.9146 (5)	0.0540 (15)
H2A	0.7143	0.5553	0.8512	0.081*
H2B	0.6886	0.5567	0.9715	0.081*
H2C	0.8696	0.5637	0.9245	0.081*
Sn1	0.24446 (5)	0.516656 (16)	0.75527 (3)	0.03282 (15)
Cl1	0.4767 (2)	0.56867 (7)	0.66429 (14)	0.0504 (4)
Cl2	0.0129 (2)	0.46313 (7)	0.84425 (14)	0.0481 (4)
Cl3	0.4835 (2)	0.46809 (6)	0.85029 (13)	0.0448 (4)
Cl4	0.0030 (2)	0.56365 (7)	0.66037 (14)	0.0489 (4)
Cl5	0.2577 (2)	0.45597 (7)	0.59993 (13)	0.0481 (4)
Cl6	0.2341 (2)	0.57647 (7)	0.91037 (13)	0.0468 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1A	0.065 (4)	0.052 (3)	0.064 (4)	0.008 (3)	0.011 (4)	0.010 (3)
C2A	0.068 (4)	0.054 (3)	0.105 (5)	0.002 (3)	0.027 (4)	0.010 (3)
C3A	0.045 (3)	0.049 (3)	0.074 (4)	0.003 (3)	0.015 (3)	0.003 (3)
C4A	0.046 (4)	0.056 (3)	0.071 (4)	0.004 (3)	0.004 (3)	0.002 (3)
C5A	0.057 (4)	0.050 (3)	0.100 (5)	0.000 (3)	0.008 (4)	−0.005 (4)
C6A	0.063 (4)	0.070 (4)	0.105 (5)	0.007 (4)	0.017 (4)	0.029 (3)
C7A	0.054 (4)	0.104 (5)	0.075 (4)	0.005 (4)	0.004 (4)	0.027 (3)
C8A	0.059 (4)	0.086 (4)	0.070 (4)	−0.004 (4)	0.005 (3)	−0.005 (3)
N1	0.067 (4)	0.044 (3)	0.056 (4)	−0.005 (3)	−0.003 (3)	0.001 (3)
C1B	0.136 (7)	0.050 (4)	0.124 (7)	0.004 (5)	−0.015 (6)	−0.011 (4)
C2B	0.169 (7)	0.064 (4)	0.132 (6)	−0.001 (5)	−0.024 (6)	−0.010 (4)
C3B	0.098 (5)	0.052 (3)	0.093 (5)	−0.001 (4)	−0.002 (4)	−0.008 (3)
C4B	0.075 (5)	0.085 (4)	0.077 (4)	−0.014 (4)	0.003 (4)	0.005 (4)
C5B	0.062 (4)	0.091 (4)	0.071 (4)	0.010 (4)	−0.002 (4)	−0.025 (4)
C6B	0.061 (4)	0.060 (4)	0.095 (5)	0.005 (4)	−0.016 (4)	−0.020 (3)
C7B	0.051 (4)	0.067 (4)	0.085 (4)	−0.007 (4)	−0.001 (3)	0.009 (3)
C8B	0.061 (4)	0.071 (4)	0.077 (4)	0.007 (4)	0.010 (4)	−0.017 (3)
N2	0.054 (3)	0.050 (3)	0.058 (4)	−0.002 (3)	0.001 (3)	−0.002 (3)
Sn1	0.0291 (2)	0.0391 (2)	0.0303 (2)	−0.00212 (19)	−0.00026 (15)	0.00088 (18)
Cl1	0.0431 (9)	0.0618 (11)	0.0462 (9)	−0.0168 (8)	0.0086 (7)	0.0063 (8)
Cl2	0.0411 (9)	0.0526 (10)	0.0506 (10)	−0.0120 (8)	0.0075 (7)	0.0093 (8)
Cl3	0.0401 (8)	0.0473 (10)	0.0469 (9)	0.0081 (7)	−0.0103 (7)	0.0022 (7)
Cl4	0.0403 (9)	0.0571 (11)	0.0493 (10)	0.0072 (8)	−0.0114 (7)	0.0090 (8)
Cl5	0.0563 (10)	0.0502 (10)	0.0379 (8)	−0.0030 (8)	0.0003 (7)	−0.0128 (7)
Cl6	0.0546 (10)	0.0503 (10)	0.0356 (8)	−0.0001 (8)	0.0014 (7)	−0.0087 (7)

Geometric parameters (Å, º)

C1A—N1	1.485 (8)	C1B—H1B2	0.97
C1A—C2A	1.517 (11)	C2B—C3B	1.462 (11)
C1A—H1A1	0.97	C2B—H2B1	0.97
C1A—H1A2	0.97	C2B—H2B2	0.97
C2A—C3A	1.481 (8)	C3B—C4B	1.39
C2A—H2A1	0.97	C3B—C8B	1.39
C2A—H2A2	0.97	C4B—C5B	1.39
C3A—C4A	1.39	C4B—H4B	0.93
C3A—C8A	1.39	C5B—C6B	1.39
C4A—C5A	1.39	C5B—H5B	0.93
C4A—H4A	0.93	C6B—C7B	1.39
C5A—C6A	1.39	C6B—H6B	0.93
C5A—H5A	0.93	C7B—C8B	1.39
C6A—C7A	1.39	C7B—H7B	0.93
C6A—H6A	0.93	C8B—H8B	0.93
C7A—C8A	1.39	N2—H2A	0.89
C7A—H7A	0.93	N2—H2B	0.89
C8A—H8A	0.93	N2—H2C	0.89
N1—H1A	0.89	Sn1—Cl1	2.4244 (17)
N1—H1B	0.89	Sn1—Cl2	2.4316 (16)
N1—H1C	0.89	Sn1—Cl3	2.4342 (17)
C1B—N2	1.477 (9)	Sn1—Cl4	2.4257 (17)
C1B—C2B	1.503 (11)	Sn1—Cl5	2.4291 (16)
C1B—H1B1	0.97	Sn1—Cl6	2.4118 (16)
N1—C1A—C2A	113.0 (6)	C1B—C2B—H2B1	109.3
N1—C1A—H1A1	109	C3B—C2B—H2B2	109.2
C2A—C1A—H1A1	109	C1B—C2B—H2B2	109.2
N1—C1A—H1A2	109	H2B1—C2B—H2B2	107.9
C2A—C1A—H1A2	109	C4B—C3B—C8B	120
H1A1—C1A—H1A2	107.8	C4B—C3B—C2B	109.7 (6)
C3A—C2A—C1A	112.4 (6)	C8B—C3B—C2B	129.0 (6)
C3A—C2A—H2A1	109.1	C3B—C4B—C5B	120
C1A—C2A—H2A1	109.1	C3B—C4B—H4B	120
C3A—C2A—H2A2	109.1	C5B—C4B—H4B	120
C1A—C2A—H2A2	109.1	C6B—C5B—C4B	120
H2A1—C2A—H2A2	107.9	C6B—C5B—H5B	120
C4A—C3A—C8A	120	C4B—C5B—H5B	120
C4A—C3A—C2A	120.6 (5)	C5B—C6B—C7B	120
C8A—C3A—C2A	119.0 (5)	C5B—C6B—H6B	120
C3A—C4A—C5A	120	C7B—C6B—H6B	120
C3A—C4A—H4A	120	C8B—C7B—C6B	120
C5A—C4A—H4A	120	C8B—C7B—H7B	120
C6A—C5A—C4A	120	C6B—C7B—H7B	120
C6A—C5A—H5A	120	C7B—C8B—C3B	120
C4A—C5A—H5A	120	C7B—C8B—H8B	120
C7A—C6A—C5A	120	C3B—C8B—H8B	120
C7A—C6A—H6A	120	C1B—N2—H2A	109.5
C5A—C6A—H6A	120	C1B—N2—H2B	109.5
C6A—C7A—C8A	120	H2A—N2—H2B	109.5
C6A—C7A—H7A	120	C1B—N2—H2C	109.5
C8A—C7A—H7A	120	H2A—N2—H2C	109.5
C7A—C8A—C3A	120	H2B—N2—H2C	109.5
C7A—C8A—H8A	120	Cl1—Sn1—Cl2	178.93 (6)
C3A—C8A—H8A	120	Cl1—Sn1—Cl3	89.22 (7)
C1A—N1—H1A	109.5	Cl1—Sn1—Cl4	91.61 (7)
C1A—N1—H1B	109.5	Cl1—Sn1—Cl5	88.93 (6)
H1A—N1—H1B	109.5	Cl1—Sn1—Cl6	90.98 (6)
C1A—N1—H1C	109.5	Cl2—Sn1—Cl3	90.48 (6)
H1A—N1—H1C	109.5	Cl2—Sn1—Cl4	88.68 (6)
H1B—N1—H1C	109.5	Cl2—Sn1—Cl5	90.04 (6)
N2—C1B—C2B	115.8 (8)	Cl2—Sn1—Cl6	90.05 (6)
N2—C1B—H1B1	108.3	Cl3—Sn1—Cl4	178.98 (6)
C2B—C1B—H1B1	108.3	Cl3—Sn1—Cl5	89.99 (6)
N2—C1B—H1B2	108.3	Cl3—Sn1—Cl6	89.41 (6)
C2B—C1B—H1B2	108.3	Cl4—Sn1—Cl5	89.44 (6)
H1B1—C1B—H1B2	107.4	Cl4—Sn1—Cl6	91.16 (6)
C3B—C2B—C1B	111.9 (7)	Cl5—Sn1—Cl6	179.39 (6)
C3B—C2B—H2B1	109.2
N1—C1A—C2A—C3A	174.6 (6)	N2—C1B—C2B—C3B	178.6 (9)
C1A—C2A—C3A—C4A	81.2 (8)	C1B—C2B—C3B—C4B	139.6 (9)
C1A—C2A—C3A—C8A	−105.3 (7)	C1B—C2B—C3B—C8B	−53.5 (14)
C8A—C3A—C4A—C5A	0	C8B—C3B—C4B—C5B	0
C2A—C3A—C4A—C5A	173.4 (5)	C2B—C3B—C4B—C5B	168.3 (7)
C3A—C4A—C5A—C6A	0	C3B—C4B—C5B—C6B	0
C4A—C5A—C6A—C7A	0	C4B—C5B—C6B—C7B	0
C5A—C6A—C7A—C8A	0	C5B—C6B—C7B—C8B	0
C6A—C7A—C8A—C3A	0	C6B—C7B—C8B—C3B	0
C4A—C3A—C8A—C7A	0	C4B—C3B—C8B—C7B	0
C2A—C3A—C8A—C7A	−173.5 (5)	C2B—C3B—C8B—C7B	−165.7 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl5	0.89	2.80	3.421 (6)	128
N1—H1B···Cl5^i	0.89	2.74	3.548 (6)	152
N1—H1C···Cl2^ii	0.89	2.92	3.606 (6)	135
N2—H2A···Cl3	0.89	2.81	3.362 (6)	122
N2—H2B···Cl3^iii	0.89	2.56	3.443 (6)	171
N2—H2C···Cl6^iv	0.89	2.70	3.546 (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.