Bis(cyclo-hexyl-ammonium) tetra-chlorido-diphenyl-stannate(IV).

The title compound, (C6H14N)2[Sn(C6H5)2Cl4], contains cyclo-hexyl-ammonium cations in general positions and a stannate(IV) anion that is located on a twofold rotation axis. The Sn(IV) atom in the complex anion is surrounded by four Cl(-) ligands and two trans-phenyl groups in a distorted octa-hedral configuration. The anions are connected with the cations through N-H⋯Cl hydrogen bonds. Every cation is involved in three N-H⋯Cl bonds to the chloride ligands of three different anions, and each chloride ligand is linked to two cations. This arrangement leads to a layered structure parallel to (010).

Related literature

For applications of organotin(IV) compounds, see: Evans & Karpel (1985 ▶); Kapoor et al. (2005 ▶). For compounds containing the [Sn(C6H5)2Cl4]2− anion in a cis or trans-conformation, see: n class="Disease">Garcia-Seijo et al. (2001 ▶); Fernandez et al. (2002 ▶); Venkatraman et al. (2004 ▶); Diop et al. (2011 ▶). For crystal structures of related tin(IV) compounds, see: Sarr et al. (2013a ▶,b ▶).

Experimental

Crystal data

(C6H14N)2[Sn(C6H5)2Cl4]

M = 615.05

Orthorhombic,

a = 13.558 (4) Å

b = 49.646 (14) Å

c = 8.058 (2) Å

V = 5424 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.35 mm−1

T = 100 K

0.30 × 0.21 × 0.05 mm

Data collection

Bruker D8 goniometer with APEX area detector

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.687, T max = 0.935

15474 measured reflections

2772 independent reflections

2563 reflections with I > 2σ(I)

R int = 0.069

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.100

S = 1.06

2772 reflections

151 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.92 e Å−3

Δρmin = −0.67 e Å−3

Absolute structure: Flack (1983 ▶), 1281 Friedel pairs

Absolute structure parameter: 0.23 (5)

Data collection: SMART (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681401109X/wm5023sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681401109X/wm5023Isup2.hkl

CCDC reference: 1002989

Additional supporting information: crystallographic information; 3D view; checkCIF report

(C6H14N)2[Sn(C6H5)2Cl4]	F(000) = 2512
Mr = 615.05	Dx = 1.506 Mg m−3
Orthorhombic, Fdd2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2d	Cell parameters from 5810 reflections
a = 13.558 (4) Å	θ = 3.0–26.2°
b = 49.646 (14) Å	µ = 1.35 mm−1
c = 8.058 (2) Å	T = 100 K
V = 5424 (3) Å3	Plate, colorless
Z = 8	0.30 × 0.21 × 0.05 mm

Bruker D8 goniometer with APEX area detector diffractometer	2772 independent reflections
Radiation source: Incoatec microsource	2563 reflections with I > 2σ(I)
Multilayer optics monochromator	Rint = 0.069
ω scans	θmax = 26.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→16
Tmin = 0.687, Tmax = 0.935	k = −62→62
15474 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.100	w = 1/[σ2(Fo2) + (0.020P)2] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.004
2772 reflections	Δρmax = 1.92 e Å−3
151 parameters	Δρmin = −0.67 e Å−3
4 restraints	Absolute structure: Flack (1983), 1281 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.23 (5)

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
Sn1	−0.0000	−0.0000	0.72474 (9)	0.02578 (15)
Cl1	−0.11741 (11)	0.01834 (3)	0.94793 (18)	0.0329 (4)
Cl2	−0.11954 (10)	0.01707 (3)	0.4982 (2)	0.0308 (4)
C1	0.0727 (4)	0.03830 (10)	0.7238 (8)	0.0285 (11)
C2	0.0212 (3)	0.06170 (10)	0.7321 (11)	0.0277 (12)
H2	−0.0484	0.0609	0.7439	0.033*
C3	0.0659 (4)	0.08670 (11)	0.7241 (9)	0.0362 (13)
H3	0.0275	0.1027	0.7226	0.043*
C4	0.1690 (4)	0.08788 (11)	0.7183 (9)	0.0357 (13)
H4	0.2016	0.1048	0.7182	0.043*
C5	0.2215 (5)	0.06497 (13)	0.7128 (10)	0.0372 (14)
H5	0.2914	0.0659	0.7060	0.045*
C6	0.1752 (4)	0.03965 (11)	0.7170 (9)	0.0297 (12)
H6	0.2134	0.0236	0.7152	0.036*
N1	0.1784 (4)	0.02720 (11)	0.2043 (9)	0.0375 (13)
H1A	0.233 (4)	0.0271 (15)	0.138 (8)	0.056*
H1B	0.142 (5)	0.0132 (10)	0.164 (8)	0.056*
H1C	0.181 (6)	0.0222 (15)	0.311 (4)	0.056*
C7	0.1431 (4)	0.05466 (11)	0.1699 (7)	0.0317 (14)
H7	0.1271	0.0557	0.0490	0.038*
C8	0.0488 (4)	0.06018 (12)	0.2660 (7)	0.0326 (15)
H8A	−0.0029	0.0472	0.2316	0.039*
H8B	0.0610	0.0577	0.3862	0.039*
C9	0.0141 (4)	0.08851 (11)	0.2336 (16)	0.0401 (14)
H9A	−0.0452	0.0921	0.3018	0.048*
H9B	−0.0050	0.0902	0.1155	0.048*
C10	0.0917 (5)	0.10933 (13)	0.2730 (9)	0.0489 (19)
H10A	0.1054	0.1093	0.3937	0.059*
H10B	0.0674	0.1274	0.2419	0.059*
C11	0.1854 (5)	0.10318 (12)	0.1787 (8)	0.0417 (17)
H11A	0.1735	0.1060	0.0588	0.050*
H11B	0.2374	0.1160	0.2138	0.050*
C12	0.2216 (5)	0.07509 (12)	0.2055 (10)	0.0343 (14)
H12A	0.2438	0.0731	0.3219	0.041*
H12B	0.2790	0.0717	0.1325	0.041*

	U11	U22	U33	U12	U13	U23
Sn1	0.0195 (2)	0.0327 (3)	0.0251 (2)	−0.0025 (2)	−0.000	−0.000
Cl1	0.0289 (7)	0.0418 (8)	0.0281 (11)	−0.0032 (6)	0.0082 (7)	−0.0044 (7)
Cl2	0.0236 (6)	0.0372 (7)	0.0316 (11)	−0.0016 (5)	−0.0062 (7)	0.0032 (7)
C1	0.040 (3)	0.031 (3)	0.014 (2)	−0.002 (2)	−0.006 (3)	0.001 (3)
C2	0.020 (3)	0.042 (3)	0.021 (3)	0.000 (2)	0.009 (4)	−0.002 (3)
C3	0.048 (4)	0.033 (3)	0.028 (3)	0.002 (2)	0.002 (4)	−0.006 (3)
C4	0.045 (3)	0.037 (3)	0.025 (3)	−0.013 (3)	−0.006 (3)	−0.002 (3)
C5	0.037 (3)	0.047 (4)	0.028 (3)	−0.012 (3)	0.001 (3)	−0.007 (4)
C6	0.025 (3)	0.041 (3)	0.023 (3)	−0.001 (2)	0.010 (3)	−0.002 (3)
N1	0.030 (3)	0.035 (3)	0.047 (4)	0.002 (2)	0.005 (3)	−0.003 (3)
C7	0.031 (3)	0.031 (3)	0.032 (3)	−0.001 (3)	0.003 (2)	−0.000 (2)
C8	0.028 (3)	0.043 (4)	0.027 (4)	−0.004 (3)	−0.001 (2)	0.001 (2)
C9	0.027 (3)	0.041 (3)	0.052 (4)	0.008 (3)	−0.002 (4)	−0.009 (5)
C10	0.060 (4)	0.032 (3)	0.056 (5)	0.005 (3)	0.003 (3)	−0.002 (3)
C11	0.047 (4)	0.037 (4)	0.041 (4)	−0.010 (3)	−0.000 (3)	−0.001 (3)
C12	0.036 (3)	0.041 (3)	0.026 (4)	−0.011 (3)	0.005 (3)	−0.001 (3)

Sn1—C1i	2.142 (5)	N1—H1B	0.91 (2)
Sn1—C1	2.142 (5)	N1—H1C	0.90 (2)
Sn1—Cl1	2.5685 (16)	C7—C12	1.498 (8)
Sn1—Cl1i	2.5686 (16)	C7—C8	1.519 (8)
Sn1—Cl2	2.5842 (17)	C7—H7	1.0000
Sn1—Cl2i	2.5843 (17)	C8—C9	1.506 (8)
C1—C2	1.357 (7)	C8—H8A	0.9900
C1—C6	1.392 (7)	C8—H8B	0.9900
C2—C3	1.383 (7)	C9—C10	1.509 (9)
C2—H2	0.9500	C9—H9A	0.9900
C3—C4	1.399 (8)	C9—H9B	0.9900
C3—H3	0.9500	C10—C11	1.511 (9)
C4—C5	1.343 (9)	C10—H10A	0.9900
C4—H4	0.9500	C10—H10B	0.9900
C5—C6	1.406 (8)	C11—C12	1.494 (9)
C5—H5	0.9500	C11—H11A	0.9900
C6—H6	0.9500	C11—H11B	0.9900
N1—C7	1.471 (8)	C12—H12A	0.9900
N1—H1A	0.91 (2)	C12—H12B	0.9900
C1i—Sn1—C1	179.6 (4)	H1B—N1—H1C	99 (7)
C1i—Sn1—Cl1	91.82 (16)	N1—C7—C12	111.1 (5)
C1—Sn1—Cl1	88.46 (17)	N1—C7—C8	110.2 (5)
C1i—Sn1—Cl1i	88.45 (17)	C12—C7—C8	112.2 (5)
C1—Sn1—Cl1i	91.82 (16)	N1—C7—H7	107.7
Cl1—Sn1—Cl1i	91.12 (8)	C12—C7—H7	107.7
C1i—Sn1—Cl2	90.00 (17)	C8—C7—H7	107.7
C1—Sn1—Cl2	89.72 (16)	C9—C8—C7	110.1 (6)
Cl1—Sn1—Cl2	89.41 (5)	C9—C8—H8A	109.6
Cl1i—Sn1—Cl2	178.38 (5)	C7—C8—H8A	109.6
C1i—Sn1—Cl2i	89.72 (16)	C9—C8—H8B	109.6
C1—Sn1—Cl2i	90.00 (17)	C7—C8—H8B	109.6
Cl1—Sn1—Cl2i	178.39 (5)	H8A—C8—H8B	108.2
Cl1i—Sn1—Cl2i	89.41 (5)	C8—C9—C10	112.6 (6)
Cl2—Sn1—Cl2i	90.10 (8)	C8—C9—H9A	109.1
C2—C1—C6	118.3 (5)	C10—C9—H9A	109.1
C2—C1—Sn1	121.5 (4)	C8—C9—H9B	109.1
C6—C1—Sn1	120.1 (4)	C10—C9—H9B	109.1
C1—C2—C3	122.7 (5)	H9A—C9—H9B	107.8
C1—C2—H2	118.6	C9—C10—C11	110.0 (6)
C3—C2—H2	118.6	C9—C10—H10A	109.7
C2—C3—C4	118.5 (5)	C11—C10—H10A	109.7
C2—C3—H3	120.8	C9—C10—H10B	109.7
C4—C3—H3	120.8	C11—C10—H10B	109.7
C5—C4—C3	119.7 (5)	H10A—C10—H10B	108.2
C5—C4—H4	120.2	C12—C11—C10	113.1 (5)
C3—C4—H4	120.2	C12—C11—H11A	109.0
C4—C5—C6	121.3 (6)	C10—C11—H11A	109.0
C4—C5—H5	119.3	C12—C11—H11B	109.0
C6—C5—H5	119.3	C10—C11—H11B	109.0
C1—C6—C5	119.3 (5)	H11A—C11—H11B	107.8
C1—C6—H6	120.3	C11—C12—C7	111.8 (5)
C5—C6—H6	120.3	C11—C12—H12A	109.3
C7—N1—H1A	99 (5)	C7—C12—H12A	109.3
C7—N1—H1B	118 (5)	C11—C12—H12B	109.3
H1A—N1—H1B	103 (6)	C7—C12—H12B	109.3
C7—N1—H1C	117 (5)	H12A—C12—H12B	107.9
H1A—N1—H1C	122 (7)
C1i—Sn1—C1—C2	93.3 (8)	C2—C3—C4—C5	3.1 (11)
Cl1—Sn1—C1—C2	−41.0 (6)	C3—C4—C5—C6	−1.6 (12)
Cl1i—Sn1—C1—C2	−132.1 (6)	C2—C1—C6—C5	−2.3 (10)
Cl2—Sn1—C1—C2	48.4 (6)	Sn1—C1—C6—C5	178.6 (6)
Cl2i—Sn1—C1—C2	138.5 (6)	C4—C5—C6—C1	1.2 (11)
C1i—Sn1—C1—C6	−87.6 (4)	N1—C7—C8—C9	178.7 (6)
Cl1—Sn1—C1—C6	138.0 (5)	C12—C7—C8—C9	54.3 (7)
Cl1i—Sn1—C1—C6	47.0 (5)	C7—C8—C9—C10	−55.7 (10)
Cl2—Sn1—C1—C6	−132.5 (5)	C8—C9—C10—C11	55.1 (10)
Cl2i—Sn1—C1—C6	−42.4 (5)	C9—C10—C11—C12	−53.5 (8)
C6—C1—C2—C3	4.0 (12)	C10—C11—C12—C7	53.4 (8)
Sn1—C1—C2—C3	−177.0 (6)	N1—C7—C12—C11	−177.3 (6)
C1—C2—C3—C4	−4.4 (12)	C8—C7—C12—C11	−53.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl2ii	0.91 (3)	2.35 (4)	3.244 (8)	166 (10)
N1—H1B···Cl1iii	0.91 (3)	2.36 (6)	3.172 (9)	148 (8)
N1—H1C···Cl2i	0.90 (3)	2.60 (7)	3.328 (9)	139 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl2i	0.91 (3)	2.35 (4)	3.244 (8)	166 (10)
N1—H1B⋯Cl1ii	0.91 (3)	2.36 (6)	3.172 (9)	148 (8)
N1—H1C⋯Cl2iii	0.90 (3)	2.60 (7)	3.328 (9)	139 (9)

Symmetry codes: (i) ; (ii) ; (iii) .