Isostructural crystal packing and hydrogen bonding in alkyl­ammonium tin(IV) chloride compounds

The three isostructural compounds butyl­ammonium hexa­chlorido­tin(IV), pentyl­ammonium hexa­chlorido­tin(IV) and hexyl­ammonium hexa­chlorido­tin(IV), (C_nH_2n+1NH₃)₂[SnCl₆], with n = 4, 5 and 6, respectively, crystallize as inorganic-organic hybrids. As such, the structures consist of layers of [SnCl₆]^2- octa­hedra, separated by hydro­carbon layers of inter­digitated butyl­ammonium, pentyl­ammonium or hexyl­ammonium cations. Corrugated layers of cations alternate with tin(IV) chloride layers. The asymmetric unit in each compound consists of an anionic component comprising one Sn and two Cl atoms on a mirror plane, and two Cl atoms in general positions; the two cations lie on another mirror plane. Application of the mirror symmetry generates octa­hedral coordination around the Sn atom. All compounds exhibit bifurcated and simple hydrogen-bonding inter­actions between the ammonium groups and the Cl atoms, with little variation in the hydrogen-bonding geometries.

S1. Comment

The bis-ammonium tetrahalometallate inorganic–organic hybrid materials of general formula (R—NH₃)₂[MX₄] [R = C_nH_{2n + 1}– and Ar–(CH₂)_m–, n = 1–18, m = 1–3, M = Pb, Sn, Cu, Mn and Cd, and X = Cl, Br and I] are characterized by the presence of two-dimensional layers of corner-sharing MX₆ octahedra, each sandwiched between two hydrocarbon layers (Mitzi, 1999). The overall structure exhibits an alternation of inorganic and organic layers. The interface between the inorganic and hydrocarbon layers consists of Cl^- and –NH₃⁺ ions, in which strong charge-assisted hydrogen bonds connect the separate layers. If the metal is tetravalent, with general formula (R–NH₃)₂[MX₆], the dimensionality is reduced and discrete MX₆ octahedra exist. This phenomenon, where the motif of the inorganic part depends on the valency of the metal, has been observed for Sn, and extensive investigations of divalent Sn have been reported (Koutselas et al., 1996; Mitzi et al., 1998; Kagan et al., 1999; Yin & Yo, 1998). However, tetravalent Sn has been less well studied and generally few compounds of the type (C_nH_{2n + 1}NH₃)₂[SnCl₆] (Lee et al., 2002, 1998 or???1997; Elleuch et al., 1999; Aruta et al., 2005, and references therein) and [C₆H₅–(CH₂)_n–NH₃]₂[SnCl₆] [n = 0 (Rademeyer, 2004a) and 1 (Rademeyer, 2004b)] have been reported in the literature. It has been found that the separation between the Sn atoms is sufficiently long, at 7.3–7.5 Å, that the hydrocarbon chains can interdigitate (Lee et al., 2002).

The aim of the present report is to describe the single-crystal structures of the three isostructural compounds containing tetravalent tin(IV) chloride and butylammonium, (I), pentylammonium, (II), or hexylammonium, (III), counter-cations. The atomic numbering scheme of the asymmetric units in all three compounds is given in Fig. 1. Other compounds with two or fewer H atoms on the N atom have been reported (Knop et al., 1983) but are not considered in this study.

The structure of compound (I), (C₄H₉NH₃)₂[SnCl₆], has been previously reported by Elleuch et al. (1996) but it was only briefly discussed. The packing arrangement is related to that of (C₂H₅NH₃)₂[SnCl₆], which crystallizes in space group P3m1 (Knop et al., 1983). Compounds (I), (II) and (III) contain alternating hydrocarbon layers of butylammonium molecules and inorganic layers of isolated SnCl₆ octahedra. The layers stack along the c axis (Fig. 2). In the directions of the a and b axes, cohesion between the inorganic and hydrocarbon layers is achieved by N—H···Cl hydrogen bonds, related to the NH₃ polar groups.

The inorganic component of the asymmetric unit of (I) contains an Sn^IV centre, two Cl atoms (Cl1 and Cl2) on a site of m symmetry at y = 1/4, and two Cl atoms (Cl3 and Cl4) on general positions (Fig. 1). Mirror symmetry generates another two Cl atoms [Cl3ⁱ and Cl4ⁱ; symmetry code: (i) x, 1/2 - y, z] to complete the octahedral coordination around Sn. A consequence of the mirror symmetry within the octahedra are four unique Sn—Cl bond lengths, in a narrow range from 2.4075 (15) to 2.4273 (10) Å and with cis Cl—Sn—Cl bond angles varying from 88.76 (4) to 92.05 (5)°. The SnCl₆ octahedra are tilted with respect to the layer they occupy; the vector through Cl1 and Cl2 makes an angle of 49.08 (2)° with the normal to the layers. Successive inorganic layers tilt in opposite directions and are separated by an interlayer spacing of 10.7418 (4) Å, corresponding to half of the unit-cell length extending perpendicular to the inorganic layer.

The asymmetric unit in (I) is completed by two symmetry-independent butylammonium cations lying across the same mirror plane at 3/4, identified as cat1 (containing N1) and cat2 (containing N2). The mirror symmetry implies an all-trans geometry for the hydrocarbon chains. The cations lie parallel to the (010) plane, with the C4···N1 vector making an angle of 25.7 (1)° with the c axis.

The two ammonium groups in the asymmetric unit of (I) display the same pattern of hydrogen-bonding interactions with Cl^- ions. Atom H1A on atom N1 forms a single hydrogen bond to Cl4, which exhibits the shortest H···A distance of 2.52 Å. Atoms H1B and H1C both form bifurcated hydrogen bonds to the acceptor atoms Cl2, Cl3 and Cl4 (twice), which are significantly longer than the simple hydrogen bond (see Table 1 and Fig. 3). Atom H2C on atom N2 forms a single hydrogen bond to Cl4, while atoms H2A and H2B both form bifurcated hydrogen bonds to the acceptor atoms Cl1 (twice) and Cl3 (twice). Cat1 forms no hydrogen bonds to Cl1 and, similarly, cat2 forms no hydrogen bonds to Cl2. The hydrogen-bonding geometry is repeated for the pentylammonium cation in (II) (see Table 2). This pattern is interrupted in (III), where atom N1 forms two single hydrogen bonds via atoms H1A and H1B, both to Cl4, and a bifurcated hydrogen bond to Cl4 and Cl2, such that cat1 forms no hydrogen bonds to either Cl1 or Cl3. Atom N2 repeats the same pattern as in (I) and (II) (Table 3 and Fig. 4).

The differences in the geometries of the inorganic layers and the SnCl₆ octahedra among the three compounds are summarized in Table 4. The shortest Sn—Cl bond length [2.400 (3) Å] is found for (III) and the longest [2.4311 (11) Å] for (II), with the average Sn—Cl bond lengths increasing from (I) to (III). The widest bond angle involving mutually cis chloride ions varies from 92.05 (5) in (I) to 92.21 (6)° in (II).

The interlayer spacing increases as a function of increasing chain length and the tilt of the SnCl₆ octahedra decreases simultaneously. There is a greater increase in the interlayer spacing in going from (I) to (II) than from (II) to (III). The tilt of the cations decreases consistently by approximately 4°, whereas the tilt of the SnCl₆ octahedra is greatest in (I) and decreases to approximately 39° for both (II) and (III). The average N···Cl distance within the hydrogen bonds is remarkably consistent.

Related literature

For related literature, see: Aruta et al. (2005); Elleuch et al. (1996, 1999); Kagan (1999); Knop et al. (1983); Koutselas et al. (1996); Lee et al. (1998, 2002); Mitzi (1999); Mitzi et al. (1998); Rademeyer (2004a, 2004b); Yin & Yo (1998).

S2. Experimental

For the preparation of (I), C₄H₉NH₂ (0.098 g, 1.34 mmol) was combined with SnCl₂ (0.119 g, 0.628 mmol) in 33% aqueous HCl (2 ml). The resulting precipitate was dissolved by refluxing for 48 h at 353 K. The solution was then cooled slowly to room temperature at 2 K h^-1, and colourless blocky crystals were harvested. For the preparation of (II), C₅H₁₁NH₂ (0.123 g, 1.41 mmol) was combined with SnCl₂ (0.119 g, 0.570 mmol) and dissolved in aqueous HCl (33%, 5 ml). The resulting solution was left open to the atmosphere, and colourless plate-like crystals were grown by slow evaporation. For the preparation of (III), C₆H₁₃NH₂ (0.155 g, 1.53 mmol) was combined with SnCl₂ (0.119 g, 0.533 mmol) and dissolved in aqueous HCl (33%, 5 ml). The resulting solution was left open to the atmosphere, and colourless plate-like crystals were grown by slow evaporation.

S3. Refinement

##AUTHOR: Please check the following modification:

H atoms were placed geomertically and refined using a riding model, with C—H distances in the range 0.96–0.98 Å, N—H distances of either 0.90 Å [(I) and (II)] or 0.89 Å [(III)], and U_iso(H) values of 1.5U_eq(C,N) or 1.2U_eq(C). The highest residual peak was 0.83 Å from atom Sn1 in (I), 0.25 Å from C8 in (II) and 2.19 Å from Cl3 in (III). The ammonium end groups on each of the two cations have their three H atoms [labelled H1A, H1B, H1C (cat1) and H2A, H2B, H2C (cat2)] disordered over two sets of positions, each with a site occupancy factor of 50%, related by the mirror plane on which the two cations are situated. Only the positions of the H atoms as they occur in the asymmetric unit are shown in the figures. The disorder is a result of the long, and by inference weak, N—H···Cl hydrogen bonds, which limits their directionality.

Computing details

For all compounds, data collection: APEX2 (Bruker, 2005); cell refinement: SAINT-Plus (Bruker, 2004). Data reduction: SAINT-Plus and XPREP (Bruker, 2004) for (I); SAINT-Plus and XPREP (Bruker 2004) for (II), (III). For all 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. The asymmetric units of (a) (I), (b) (II) and (c) (III), showing the atomic numbering scheme. Displacement ellipsoids are shown at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code: (i) x, 1/2 - y, z.]
	Fig. 2. The packing of (I), viewed along the b axis.
	Fig. 3. A magnified view of the hydrogen bonding of the two butylammonium cations in (I). Each cation has two bifurcated and one simple H···Cl bond. The same geometry is seen in (II).
	Fig. 4. A magnified view of the hydrogen bonding of the two hexylammonium cations in (III). Cat1 has one bifurcated and two simple H···Cl bonds. Cat 2 has two bifurcated and one simple H···Cl bond as in (I) and (II).

(I) butylammonium hexachloridotin(IV)

Crystal data

(C4H12N)2[SnCl6]	F(000) = 952
Mr = 479.68	Dx = 1.675 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 6210 reflections
a = 12.1624 (4) Å	θ = 2.5–28.3°
b = 7.2782 (2) Å	µ = 2.17 mm^−1
c = 21.4837 (7) Å	T = 243 K
V = 1901.75 (10) Å^3	Blocky, colourless
Z = 4	0.26 × 0.24 × 0.1 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	2088 reflections with I > 2σ(I)
ω scans	Rint = 0.062
Absorption correction: integration (XPREP; Bruker, 2004)	θmax = 28°, θmin = 1.9°
Tmin = 0.535, Tmax = 0.822	h = −15→16
14713 measured reflections	k = −9→9
2470 independent reflections	l = −28→27

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0367P)^2 + 3.3848P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.038	(Δ/σ)max < 0.001
wR(F^2) = 0.103	Δρmax = 0.54 e Å^−3
S = 1.13	Δρmin = −0.53 e Å^−3
2470 reflections	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
98 parameters	Extinction coefficient: 0.0113 (7)
72 restraints

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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	Occ. (<1)
C1	0.6054 (8)	0.75	0.6418 (4)	0.100 (3)
H1D	0.6493	0.8588	0.6521	0.12*	0.5
H1E	0.6493	0.6412	0.6521	0.12*	0.5
C2	0.5051 (8)	0.75	0.6803 (4)	0.136 (4)
H2D	0.4615	0.6415	0.6693	0.163*	0.5
H2E	0.4615	0.8585	0.6693	0.163*	0.5
C3	0.5220 (10)	0.75	0.7491 (4)	0.143 (4)
H3A	0.5636	0.8592	0.7616	0.172*	0.5
H3B	0.5636	0.6408	0.7616	0.172*	0.5
C4	0.4111 (12)	0.75	0.7798 (6)	0.200 (7)
H4A	0.4199	0.7296	0.8241	0.301*	0.5
H4B	0.3663	0.6528	0.7622	0.301*	0.5
H4C	0.3756	0.8676	0.7729	0.301*	0.5
N1	0.5833 (4)	0.75	0.5769 (3)	0.0607 (14)
H1A	0.5198	0.6903	0.5696	0.091*	0.5
H1B	0.6384	0.6931	0.5566	0.091*	0.5
H1C	0.5777	0.8666	0.5633	0.091*	0.5
C5	0.9087 (8)	0.75	0.3745 (4)	0.120 (4)
H5A	0.9515	0.642	0.362	0.144*	0.5
H5B	0.9515	0.858	0.362	0.144*	0.5
C6	0.8103 (9)	0.75	0.3375 (4)	0.153 (4)
H6A	0.7671	0.8583	0.3491	0.183*	0.5
H6B	0.7671	0.6417	0.3491	0.183*	0.5
C7	0.8219 (9)	0.75	0.2682 (4)	0.146 (5)
H7A	0.8622	0.6407	0.2544	0.175*	0.5
H7B	0.8622	0.8593	0.2544	0.175*	0.5
C8	0.7073 (11)	0.75	0.2410 (6)	0.200 (7)
H8A	0.6736	0.8692	0.2476	0.301*	0.5
H8B	0.6635	0.656	0.2612	0.301*	0.5
H8C	0.7112	0.7248	0.1967	0.301*	0.5
N2	0.9055 (4)	0.75	0.4391 (3)	0.0612 (14)
H2A	0.9004	0.8664	0.453	0.092*	0.5
H2B	0.9672	0.6981	0.4541	0.092*	0.5
H2C	0.8467	0.6855	0.4521	0.092*	0.5
Sn1	0.74611 (2)	0.25	0.51434 (2)	0.03951 (16)
Cl1	0.89672 (12)	0.25	0.44048 (8)	0.0585 (4)
Cl2	0.59657 (12)	0.25	0.58776 (8)	0.0582 (4)
Cl3	0.83950 (8)	0.48901 (14)	0.57185 (6)	0.0553 (3)
Cl4	0.65350 (8)	0.48666 (14)	0.45444 (5)	0.0530 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.111 (6)	0.123 (8)	0.065 (4)	0	−0.002 (4)	0
C2	0.132 (7)	0.203 (10)	0.072 (4)	0	0.016 (5)	0
C3	0.179 (10)	0.182 (11)	0.070 (4)	0	0.019 (6)	0
C4	0.237 (14)	0.233 (17)	0.132 (10)	0	0.094 (11)	0
N1	0.051 (3)	0.069 (4)	0.062 (3)	0	0.007 (2)	0
C5	0.108 (7)	0.192 (11)	0.060 (4)	0	−0.006 (4)	0
C6	0.145 (8)	0.241 (12)	0.072 (5)	0	−0.024 (5)	0
C7	0.159 (9)	0.211 (12)	0.069 (5)	0	−0.028 (6)	0
C8	0.183 (12)	0.287 (19)	0.131 (11)	0	−0.072 (10)	0
N2	0.054 (3)	0.073 (4)	0.057 (3)	0	0.000 (2)	0
Sn1	0.0286 (2)	0.0297 (2)	0.0602 (3)	0	−0.00119 (15)	0
Cl1	0.0409 (7)	0.0607 (9)	0.0739 (11)	0	0.0154 (7)	0
Cl2	0.0392 (7)	0.0604 (9)	0.0750 (11)	0	0.0127 (7)	0
Cl3	0.0486 (5)	0.0420 (5)	0.0754 (7)	−0.0096 (4)	−0.0093 (5)	−0.0098 (5)
Cl4	0.0507 (5)	0.0384 (5)	0.0698 (7)	0.0080 (4)	−0.0084 (5)	0.0071 (5)

Geometric parameters (Å, º)

C1—N1	1.422 (10)	C5—H5A	0.98
C1—C2	1.474 (8)	C5—H5B	0.98
C1—H1D	0.98	C6—C7	1.496 (8)
C1—H1E	0.98	C6—H6A	0.98
C2—C3	1.492 (8)	C6—H6B	0.98
C2—H2D	0.98	C7—C8	1.511 (9)
C2—H2E	0.98	C7—H7A	0.98
C3—C4	1.501 (9)	C7—H7B	0.98
C3—H3A	0.98	C8—H8A	0.97
C3—H3B	0.98	C8—H8B	0.97
C4—H4A	0.97	C8—H8C	0.97
C4—H4B	0.97	N2—H2A	0.9
C4—H4C	0.97	N2—H2B	0.9
N1—H1A	0.9	N2—H2C	0.9
N1—H1B	0.9	Sn1—Cl1	2.4235 (15)
N1—H1C	0.9	Sn1—Cl2	2.4075 (15)
C5—N2	1.388 (10)	Sn1—Cl3	2.4172 (10)
C5—C6	1.438 (9)	Sn1—Cl4	2.4273 (10)
N1—C1—C2	113.2 (8)	H5A—C5—H5B	106.7
N1—C1—H1D	108.9	C5—C6—C7	118.2 (9)
C2—C1—H1D	108.9	C5—C6—H6A	107.7
N1—C1—H1E	108.9	C7—C6—H6A	107.7
C2—C1—H1E	108.9	C5—C6—H6B	107.7
H1D—C1—H1E	107.8	C7—C6—H6B	107.7
C1—C2—C3	116.1 (9)	H6A—C6—H6B	107.1
C1—C2—H2D	108.2	C6—C7—C8	107.3 (9)
C3—C2—H2D	108.2	C6—C7—H7A	110.2
C1—C2—H2E	108.2	C8—C7—H7A	110.2
C3—C2—H2E	108.2	C6—C7—H7B	110.2
H2D—C2—H2E	107.4	C8—C7—H7B	110.2
C2—C3—C4	108.1 (9)	H7A—C7—H7B	108.5
C2—C3—H3A	110.1	C7—C8—H8A	109.5
C4—C3—H3A	110.1	C7—C8—H8B	109.5
C2—C3—H3B	110.1	H8A—C8—H8B	109.5
C4—C3—H3B	110.1	C7—C8—H8C	109.5
H3A—C3—H3B	108.4	H8A—C8—H8C	109.5
C3—C4—H4A	109.5	H8B—C8—H8C	109.5
C3—C4—H4B	109.5	C5—N2—H2A	109.5
H4A—C4—H4B	109.5	C5—N2—H2B	109.5
C3—C4—H4C	109.5	H2A—N2—H2B	109.5
H4A—C4—H4C	109.5	C5—N2—H2C	109.5
H4B—C4—H4C	109.5	H2A—N2—H2C	109.5
C1—N1—H1A	109.5	H2B—N2—H2C	109.5
C1—N1—H1B	109.5	Cl1—Sn1—Cl2	179.97 (6)
H1A—N1—H1B	109.5	Cl1—Sn1—Cl3	88.83 (4)
C1—N1—H1C	109.5	Cl1—Sn1—Cl4	90.21 (4)
H1A—N1—H1C	109.5	Cl2—Sn1—Cl3	91.15 (4)
H1B—N1—H1C	109.5	Cl2—Sn1—Cl4	89.82 (4)
N2—C5—C6	122.0 (9)	Cl3—Sn1—Cl3^i	92.05 (5)
N2—C5—H5A	106.8	Cl3—Sn1—Cl4	88.76 (4)
C6—C5—H5A	106.8	Cl3^i—Sn1—Cl4	178.72 (4)
N2—C5—H5B	106.8	Cl4^i—Sn1—Cl4	90.41 (5)
C6—C5—H5B	106.8
N1—C1—C2—C3	180	N2—C5—C6—C7	180
C1—C2—C3—C4	180	C5—C6—C7—C8	180

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl4^ii	0.9	2.52	3.423 (5)	177
N1—H1B···Cl4	0.9	2.67	3.365 (5)	135
N1—H1B···Cl3	0.9	2.88	3.651 (5)	145
N1—H1C···Cl4^iii	0.9	2.73	3.365 (5)	128
N1—H1C···Cl2^iv	0.9	2.85	3.6502 (5)	149
N2—H2A···Cl1^iv	0.9	2.81	3.6408 (2)	155
N2—H2A···Cl3^iii	0.9	2.86	3.519 (5)	131
N2—H2B···Cl3^v	0.9	2.77	3.564 (5)	147
N2—H2B···Cl1^v	0.9	2.83	3.533 (6)	136
N2—H2C···Cl4	0.9	2.76	3.630 (5)	163

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

(II) pentylammonium hexachloridotin(IV)

Crystal data

(C5H14N)2[SnCl6]	F(000) = 1016
Mr = 507.73	Dx = 1.558 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 4930 reflections
a = 12.2351 (5) Å	θ = 2.4–27.8°
b = 7.2021 (3) Å	µ = 1.91 mm^−1
c = 24.5723 (9) Å	T = 243 K
V = 2165.27 (15) Å^3	Plate, colourless
Z = 4	0.32 × 0.3 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	2038 reflections with I > 2σ(I)
ω scans	Rint = 0.043
Absorption correction: integration (XPREP; Bruker, 2004)	θmax = 28°, θmin = 1.7°
Tmin = 0.571, Tmax = 0.893	h = −15→16
16581 measured reflections	k = −9→9
2820 independent reflections	l = −32→27

Refinement

Refinement on F^2	92 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0464P)^2 + 4.3427P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.118	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.82 e Å^−3
2820 reflections	Δρmin = −0.59 e Å^−3
109 parameters

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

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	Occ. (<1)
C1	0.6009 (7)	0.75	0.6209 (3)	0.094 (3)
H1D	0.6451	0.8597	0.6293	0.113*	0.5
H1E	0.6451	0.6403	0.6293	0.113*	0.5
C2	0.5046 (8)	0.75	0.6566 (3)	0.115 (3)
H2D	0.4603	0.6402	0.6485	0.138*	0.5
H2E	0.4603	0.8598	0.6485	0.138*	0.5
C3	0.5321 (9)	0.75	0.7170 (3)	0.123 (4)
H3A	0.5756	0.6398	0.7259	0.148*	0.5
H3B	0.5756	0.8602	0.7259	0.148*	0.5
C4	0.4288 (10)	0.75	0.7503 (4)	0.167 (5)
H4A	0.3854	0.6399	0.7412	0.201*	0.5
H4B	0.3854	0.8601	0.7412	0.201*	0.5
C5	0.4529 (12)	0.75	0.8105 (4)	0.169 (6)
H5A	0.3848	0.75	0.8306	0.254*
H5B	0.4947	0.86	0.8197	0.254*	0.5
H5C	0.4947	0.64	0.8197	0.254*	0.5
N1	0.5782 (5)	0.75	0.5640 (2)	0.0605 (15)
H1A	0.5149	0.69	0.5578	0.091*	0.5
H1B	0.6327	0.6922	0.5462	0.091*	0.5
H1C	0.5727	0.8678	0.5521	0.091*	0.5
C6	0.9190 (7)	0.75	0.3901 (3)	0.103 (3)
H6A	0.9629	0.6406	0.3809	0.124*	0.5
H6B	0.9629	0.8594	0.3809	0.124*	0.5
C7	0.8240 (8)	0.75	0.3549 (3)	0.117 (3)
H7A	0.78	0.8595	0.3638	0.141*	0.5
H7B	0.78	0.6405	0.3638	0.141*	0.5
C8	0.8432 (9)	0.75	0.2943 (3)	0.126 (4)
H8A	0.8857	0.8601	0.2842	0.152*	0.5
H8B	0.8857	0.6399	0.2842	0.152*	0.5
C9	0.7371 (9)	0.75	0.2636 (4)	0.165 (5)
H9A	0.6949	0.6401	0.2741	0.199*	0.5
H9B	0.6949	0.8599	0.2741	0.199*	0.5
C10	0.7517 (11)	0.75	0.2030 (4)	0.184 (7)
H10A	0.6806	0.75	0.1856	0.275*
H10B	0.7919	0.64	0.1922	0.275*	0.5
H10C	0.7919	0.86	0.1922	0.275*	0.5
N2	0.9041 (5)	0.75	0.4467 (2)	0.0595 (15)
H2A	0.8984	0.8677	0.4587	0.089*	0.5
H2B	0.9617	0.6949	0.4628	0.089*	0.5
H2C	0.8427	0.6874	0.455	0.089*	0.5
Sn1	0.74770 (3)	0.25	0.51138 (2)	0.04132 (16)
Cl1	0.90468 (12)	0.25	0.45078 (7)	0.0542 (4)
Cl2	0.58916 (13)	0.25	0.56964 (9)	0.0629 (5)
Cl3	0.83338 (9)	0.49109 (15)	0.56432 (5)	0.0541 (3)
Cl4	0.66184 (9)	0.48860 (15)	0.45598 (5)	0.0558 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.085 (6)	0.129 (8)	0.068 (4)	0	0.000 (4)	0
C2	0.102 (6)	0.169 (9)	0.073 (4)	0	0.012 (4)	0
C3	0.143 (8)	0.157 (9)	0.070 (4)	0	0.018 (5)	0
C4	0.184 (10)	0.227 (12)	0.091 (5)	0	0.046 (6)	0
C5	0.225 (15)	0.199 (14)	0.083 (5)	0	0.053 (7)	0
N1	0.055 (3)	0.063 (4)	0.063 (3)	0	0.009 (3)	0
C6	0.090 (6)	0.160 (9)	0.059 (4)	0	−0.004 (4)	0
C7	0.101 (6)	0.182 (9)	0.069 (4)	0	−0.016 (4)	0
C8	0.137 (8)	0.175 (9)	0.068 (4)	0	−0.019 (5)	0
C9	0.165 (9)	0.243 (12)	0.088 (5)	0	−0.042 (6)	0
C10	0.205 (15)	0.259 (18)	0.086 (6)	0	−0.053 (7)	0
N2	0.054 (3)	0.068 (4)	0.056 (3)	0	−0.003 (3)	0
Sn1	0.0282 (2)	0.0266 (2)	0.0692 (3)	0	−0.00223 (18)	0
Cl1	0.0380 (7)	0.0541 (9)	0.0705 (11)	0	0.0092 (7)	0
Cl2	0.0344 (8)	0.0592 (10)	0.0951 (14)	0	0.0131 (8)	0
Cl3	0.0474 (6)	0.0374 (5)	0.0776 (8)	−0.0072 (5)	−0.0068 (5)	−0.0094 (5)
Cl4	0.0498 (6)	0.0345 (5)	0.0830 (9)	0.0072 (5)	−0.0128 (6)	0.0075 (5)

Geometric parameters (Å, º)

C1—N1	1.425 (9)	C6—H6A	0.98
C1—C2	1.469 (8)	C6—H6B	0.98
C1—H1D	0.98	C7—C8	1.508 (8)
C1—H1E	0.98	C7—H7A	0.98
C2—C3	1.522 (8)	C7—H7B	0.98
C2—H2D	0.98	C8—C9	1.501 (9)
C2—H2E	0.98	C8—H8A	0.98
C3—C4	1.505 (9)	C8—H8B	0.98
C3—H3A	0.98	C9—C10	1.499 (9)
C3—H3B	0.98	C9—H9A	0.98
C4—C5	1.508 (9)	C9—H9B	0.98
C4—H4A	0.98	C10—H10A	0.97
C4—H4B	0.98	C10—H10B	0.97
C5—H5A	0.97	C10—H10C	0.97
C5—H5B	0.97	N2—H2A	0.9
C5—H5C	0.97	N2—H2B	0.9
N1—H1A	0.9	N2—H2C	0.9
N1—H1B	0.9	Sn1—Cl1	2.4303 (16)
N1—H1C	0.9	Sn1—Cl2	2.4109 (17)
C6—N2	1.403 (9)	Sn1—Cl3	2.4096 (11)
C6—C7	1.450 (8)	Sn1—Cl4	2.4311 (11)
N1—C1—C2	115.5 (8)	H6A—C6—H6B	107
N1—C1—H1D	108.4	C6—C7—C8	117.7 (8)
C2—C1—H1D	108.4	C6—C7—H7A	107.9
N1—C1—H1E	108.4	C8—C7—H7A	107.9
C2—C1—H1E	108.4	C6—C7—H7B	107.9
H1D—C1—H1E	107.5	C8—C7—H7B	107.9
C1—C2—C3	114.0 (8)	H7A—C7—H7B	107.2
C1—C2—H2D	108.8	C9—C8—C7	111.1 (8)
C3—C2—H2D	108.8	C9—C8—H8A	109.4
C1—C2—H2E	108.8	C7—C8—H8A	109.4
C3—C2—H2E	108.8	C9—C8—H8B	109.4
H2D—C2—H2E	107.7	C7—C8—H8B	109.4
C4—C3—C2	110.1 (8)	H8A—C8—H8B	108
C4—C3—H3A	109.6	C10—C9—C8	113.3 (9)
C2—C3—H3A	109.6	C10—C9—H9A	108.9
C4—C3—H3B	109.6	C8—C9—H9A	108.9
C2—C3—H3B	109.6	C10—C9—H9B	108.9
H3A—C3—H3B	108.1	C8—C9—H9B	108.9
C3—C4—C5	111.6 (9)	H9A—C9—H9B	107.7
C3—C4—H4A	109.3	C9—C10—H10A	109.5
C5—C4—H4A	109.3	C9—C10—H10B	109.5
C3—C4—H4B	109.3	H10A—C10—H10B	109.5
C5—C4—H4B	109.3	C9—C10—H10C	109.5
H4A—C4—H4B	108	H10A—C10—H10C	109.5
C4—C5—H5A	109.5	H10B—C10—H10C	109.5
C4—C5—H5B	109.5	C6—N2—H2A	109.5
H5A—C5—H5B	109.5	C6—N2—H2B	109.5
C4—C5—H5C	109.5	H2A—N2—H2B	109.5
H5A—C5—H5C	109.5	C6—N2—H2C	109.5
H5B—C5—H5C	109.5	H2A—N2—H2C	109.5
C1—N1—H1A	109.5	H2B—N2—H2C	109.5
C1—N1—H1B	109.5	Cl1—Sn1—Cl2	178.64 (7)
H1A—N1—H1B	109.5	Cl1—Sn1—Cl3	89.26 (4)
C1—N1—H1C	109.5	Cl1—Sn1—Cl4	89.91 (4)
H1A—N1—H1C	109.5	Cl2—Sn1—Cl3	91.69 (5)
H1B—N1—H1C	109.5	Cl2—Sn1—Cl4	89.13 (5)
N2—C6—C7	119.2 (8)	Cl3—Sn1—Cl3^i	92.21 (6)
N2—C6—H6A	107.5	Cl3—Sn1—Cl4^i	178.59 (5)
C7—C6—H6A	107.5	Cl3—Sn1—Cl4	88.91 (4)
N2—C6—H6B	107.5	Cl4^i—Sn1—Cl4	89.96 (6)
C7—C6—H6B	107.5
N1—C1—C2—C3	180	N2—C6—C7—C8	180
C1—C2—C3—C4	180	C6—C7—C8—C9	180
C2—C3—C4—C5	180	C7—C8—C9—C10	180

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl4^ii	0.90	2.54	3.438 (5)	177
N1—H1B···Cl4	0.90	2.68	3.411 (5)	139
N1—H1B···Cl3	0.90	2.89	3.636 (5)	142
N1—H1C···Cl4^iii	0.90	2.80	3.411 (5)	126
N1—H1C···Cl2^iv	0.90	2.79	3.6062 (4)	151
N2—H2A···Cl1^iv	0.90	2.76	3.6024 (2)	156
N2—H2A···Cl3^iii	0.90	2.90	3.546 (5)	130
N2—H2B···Cl3^v	0.90	2.92	3.661 (5)	141
N2—H2B···Cl1^v	0.90	2.71	3.437 (6)	139
N2—H2C···Cl4	0.90	2.64	3.519 (5)	167

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

(III) hexylammonium hexachloridotin(IV)

Crystal data

(C6H16N)2[SnCl6]	F(000) = 1080
Mr = 535.79	Dx = 1.478 Mg m^−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 4671 reflections
a = 12.3622 (3) Å	θ = 2.3–26.5°
b = 7.3179 (2) Å	µ = 1.72 mm^−1
c = 26.6245 (6) Å	T = 293 K
V = 2408.59 (10) Å^3	Plate, colourless
Z = 4	0.36 × 0.28 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer	2094 reflections with I > 2σ(I)
ω scans	Rint = 0.055
Absorption correction: integration XPREP (Bruker, 2004)	θmax = 28°, θmin = 1.5°
Tmin = 0.603, Tmax = 0.856	h = −16→16
18912 measured reflections	k = −9→9
3129 independent reflections	l = −35→34

Refinement

Refinement on F^2	112 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.075	w = 1/[σ^2(Fo^2) + (0.0677P)^2 + 14.1291P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.217	(Δ/σ)max < 0.001
S = 1.11	Δρmax = 0.68 e Å^−3
3129 reflections	Δρmin = −0.91 e Å^−3
121 parameters

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 2004)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
C1	0.6071 (15)	0.75	0.6082 (6)	0.141 (6)
H1D	0.6511	0.8572	0.6148	0.17*	0.5
H1E	0.6511	0.6428	0.6148	0.17*	0.5
C2	0.5101 (14)	0.75	0.6434 (5)	0.160 (6)
H2D	0.4661	0.8574	0.6372	0.192*	0.5
H2E	0.4661	0.6426	0.6372	0.192*	0.5
C3	0.5486 (15)	0.75	0.6974 (5)	0.177 (7)
H3A	0.593	0.8572	0.7032	0.212*	0.5
H3B	0.593	0.6428	0.7032	0.212*	0.5
C4	0.4548 (15)	0.75	0.7342 (5)	0.200 (8)
H4A	0.4103	0.6425	0.7291	0.24*	0.5
H4B	0.4103	0.8575	0.7291	0.24*	0.5
C5	0.5020 (17)	0.75	0.7877 (6)	0.211 (9)
H5A	0.5467	0.6425	0.7927	0.253*	0.5
H5B	0.5467	0.8575	0.7927	0.253*	0.5
C6	0.409 (2)	0.75	0.8251 (7)	0.242 (13)
H6A	0.4376	0.75	0.8587	0.363*
H6B	0.3657	0.6429	0.8201	0.363*	0.5
H6C	0.3657	0.8571	0.8201	0.363*	0.5
N1	0.5761 (10)	0.75	0.5584 (5)	0.100 (4)
H1A	0.514	0.6896	0.5551	0.15*	0.5
H1B	0.6269	0.6958	0.54	0.15*	0.5
H1C	0.5673	0.8646	0.548	0.15*	0.5
C7	0.9203 (16)	0.75	0.4006 (6)	0.154 (7)
H7A	0.9631	0.6434	0.392	0.185*	0.5
H7B	0.9631	0.8566	0.392	0.185*	0.5
C8	0.8216 (15)	0.75	0.3675 (5)	0.180 (7)
H8A	0.7782	0.8573	0.3747	0.215*	0.5
H8B	0.7782	0.6427	0.3747	0.215*	0.5
C9	0.8527 (15)	0.75	0.3125 (5)	0.196 (7)
H9A	0.8958	0.6426	0.3051	0.236*	0.5
H9B	0.8958	0.8574	0.3051	0.236*	0.5
C10	0.7508 (16)	0.75	0.2799 (6)	0.229 (9)
H10A	0.7074	0.8577	0.2866	0.275*	0.5
H10B	0.7074	0.6423	0.2866	0.275*	0.5
C11	0.7904 (18)	0.75	0.2251 (6)	0.249 (10)
H11A	0.8343	0.8575	0.2188	0.298*	0.5
H11B	0.8343	0.6425	0.2188	0.298*	0.5
C12	0.693 (2)	0.75	0.1906 (8)	0.298 (16)
H12A	0.7172	0.75	0.1563	0.447*
H12B	0.6505	0.8571	0.1968	0.447*	0.5
H12C	0.6505	0.6429	0.1968	0.447*	0.5
N2	0.9061 (11)	0.75	0.4514 (4)	0.102 (4)
H2A	0.9007	0.8646	0.4623	0.153*	0.5
H2B	0.9624	0.696	0.466	0.153*	0.5
H2C	0.8459	0.6894	0.459	0.153*	0.5
Sn1	0.74764 (5)	0.25	0.50943 (3)	0.0619 (3)
Cl1	0.9014 (2)	0.25	0.45304 (14)	0.0776 (9)
Cl2	0.5931 (2)	0.25	0.56400 (16)	0.0862 (10)
Cl3	0.83397 (17)	0.4872 (3)	0.55771 (10)	0.0795 (7)
Cl4	0.66125 (17)	0.4853 (3)	0.45906 (10)	0.0792 (7)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.128 (12)	0.183 (15)	0.113 (7)	0	−0.008 (7)	0
C2	0.156 (13)	0.208 (15)	0.115 (7)	0	0.011 (8)	0
C3	0.188 (15)	0.225 (16)	0.117 (7)	0	0.006 (8)	0
C4	0.228 (17)	0.243 (17)	0.130 (8)	0	0.036 (10)	0
C5	0.26 (2)	0.248 (19)	0.128 (8)	0	0.035 (12)	0
C6	0.32 (3)	0.26 (3)	0.148 (12)	0	0.079 (18)	0
N1	0.083 (8)	0.107 (9)	0.110 (6)	0	0.002 (6)	0
C7	0.152 (14)	0.211 (17)	0.098 (6)	0	0.013 (8)	0
C8	0.181 (15)	0.239 (17)	0.119 (8)	0	−0.015 (8)	0
C9	0.207 (16)	0.265 (18)	0.118 (7)	0	−0.020 (9)	0
C10	0.239 (18)	0.30 (2)	0.145 (9)	0	−0.053 (11)	0
C11	0.28 (2)	0.33 (2)	0.138 (9)	0	−0.057 (13)	0
C12	0.35 (3)	0.37 (4)	0.175 (15)	0	−0.11 (2)	0
N2	0.102 (9)	0.107 (9)	0.097 (6)	0	0.021 (6)	0
Sn1	0.0432 (4)	0.0403 (4)	0.1023 (7)	0	−0.0021 (4)	0
Cl1	0.0518 (15)	0.0732 (19)	0.108 (3)	0	0.0138 (16)	0
Cl2	0.0516 (16)	0.075 (2)	0.132 (3)	0	0.0207 (18)	0
Cl3	0.0683 (12)	0.0540 (11)	0.1163 (18)	−0.0125 (10)	−0.0106 (12)	−0.0146 (12)
Cl4	0.0667 (12)	0.0510 (11)	0.1201 (19)	0.0095 (9)	−0.0147 (12)	0.0128 (11)

Geometric parameters (Å, º)

C1—N1	1.380 (18)	C7—H7A	0.97
C1—C2	1.52 (2)	C7—H7B	0.97
C1—H1D	0.97	C8—C9	1.51 (2)
C1—H1E	0.97	C8—H8A	0.97
C2—C3	1.51 (2)	C8—H8B	0.97
C2—H2D	0.97	C9—C10	1.53 (2)
C2—H2E	0.97	C9—H9A	0.97
C3—C4	1.52 (2)	C9—H9B	0.97
C3—H3A	0.97	C10—C11	1.539 (10)
C3—H3B	0.97	C10—H10A	0.97
C4—C5	1.54 (2)	C10—H10B	0.97
C4—H4A	0.97	C11—C12	1.51 (2)
C4—H4B	0.97	C11—H11A	0.97
C5—C6	1.52 (2)	C11—H11B	0.97
C5—H5A	0.97	C12—H12A	0.96
C5—H5B	0.97	C12—H12B	0.96
C6—H6A	0.96	C12—H12C	0.96
C6—H6B	0.96	N2—H2A	0.89
C6—H6C	0.96	N2—H2B	0.89
N1—H1A	0.89	N2—H2C	0.89
N1—H1B	0.89	Sn1—Cl1	2.423 (3)
N1—H1C	0.89	Sn1—Cl2	2.400 (3)
C7—N2	1.365 (17)	Sn1—Cl3	2.409 (2)
C7—C8	1.50 (2)	Sn1—Cl4	2.430 (2)
N1—C1—C2	111.9 (14)	H7A—C7—H7B	107.1
N1—C1—H1D	109.2	C7—C8—C9	111.1 (12)
C2—C1—H1D	109.2	C7—C8—H8A	109.4
N1—C1—H1E	109.2	C9—C8—H8A	109.4
C2—C1—H1E	109.2	C7—C8—H8B	109.4
H1D—C1—H1E	107.9	C9—C8—H8B	109.4
C3—C2—C1	109.7 (11)	H8A—C8—H8B	108
C3—C2—H2D	109.7	C8—C9—C10	109.9 (11)
C1—C2—H2D	109.7	C8—C9—H9A	109.7
C3—C2—H2E	109.7	C10—C9—H9A	109.7
C1—C2—H2E	109.7	C8—C9—H9B	109.7
H2D—C2—H2E	108.2	C10—C9—H9B	109.7
C2—C3—C4	112.0 (11)	H9A—C9—H9B	108.2
C2—C3—H3A	109.2	C9—C10—C11	106.1 (11)
C4—C3—H3A	109.2	C9—C10—H10A	110.5
C2—C3—H3B	109.2	C11—C10—H10A	110.5
C4—C3—H3B	109.2	C9—C10—H10B	110.5
H3A—C3—H3B	107.9	C11—C10—H10B	110.5
C3—C4—C5	108.0 (11)	H10A—C10—H10B	108.7
C3—C4—H4A	110.1	C12—C11—C10	108.8 (13)
C5—C4—H4A	110.1	C12—C11—H11A	109.9
C3—C4—H4B	110.1	C10—C11—H11A	109.9
C5—C4—H4B	110.1	C12—C11—H11B	109.9
H4A—C4—H4B	108.4	C10—C11—H11B	109.9
C6—C5—C4	108.7 (12)	H11A—C11—H11B	108.3
C6—C5—H5A	110	C11—C12—H12A	109.5
C4—C5—H5A	110	C11—C12—H12B	109.5
C6—C5—H5B	110	H12A—C12—H12B	109.5
C4—C5—H5B	110	C11—C12—H12C	109.5
H5A—C5—H5B	108.3	H12A—C12—H12C	109.5
C5—C6—H6A	109.5	H12B—C12—H12C	109.5
C5—C6—H6B	109.5	C7—N2—H2A	109.5
H6A—C6—H6B	109.5	C7—N2—H2B	109.5
C5—C6—H6C	109.5	H2A—N2—H2B	109.5
H6A—C6—H6C	109.5	C7—N2—H2C	109.5
H6B—C6—H6C	109.5	H2A—N2—H2C	109.5
C1—N1—H1A	109.5	H2B—N2—H2C	109.5
C1—N1—H1B	109.5	Cl1—Sn1—Cl2	178.95 (13)
H1A—N1—H1B	109.5	Cl1—Sn1—Cl3	89.03 (9)
C1—N1—H1C	109.5	Cl1—Sn1—Cl4	90.16 (9)
H1A—N1—H1C	109.5	Cl2—Sn1—Cl3	91.70 (9)
H1B—N1—H1C	109.5	Cl2—Sn1—Cl4	89.10 (9)
N2—C7—C8	118.4 (15)	Cl3—Sn1—Cl3^i	92.18 (12)
N2—C7—H7A	107.7	Cl3—Sn1—Cl4	88.78 (8)
C8—C7—H7A	107.7	Cl3^i—Sn1—Cl4	178.73 (9)
N2—C7—H7B	107.7	Cl4^i—Sn1—Cl4	90.25 (11)
C8—C7—H7B	107.7
N1—C1—C2—C3	180	N2—C7—C8—C9	180
C1—C2—C3—C4	180	C7—C8—C9—C10	180
C2—C3—C4—C5	180	C8—C9—C10—C11	180
C3—C4—C5—C6	180	C9—C10—C11—C12	180

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl4^ii	0.89	2.54	3.434 (10)	177
N1—H1B···Cl4	0.89	2.68	3.443 (10)	144
N1—H1C···Cl4^iii	0.89	2.86	3.443 (10)	125
N1—H1C···Cl2^iv	0.89	2.87	3.6680 (9)	150
N2—H2A···Cl1^iv	0.89	2.83	3.6597 (3)	156
N2—H2A···Cl3^iii	0.89	2.88	3.537 (10)	132
N2—H2B···Cl3^v	0.89	2.92	3.660 (12)	142
N2—H2B···Cl1^v	0.89	2.76	3.484 (13)	139
N2—H2C···Cl4	0.89	2.73	3.599 (11)	167

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