Bis(3-hy-droxy-methyl-anilinium) hexa-chloridostannate(IV).

In the title compound, (C(7)H(10)NO)(2)[SnCl(6)], the Sn(IV) atom, located on an inversion center, exists in an octa-hedral coordination environment. The crystal structure exhibits alternating organic and inorganic layers parallel to ([Formula: see text]01). The cations and anions are linked via inter-molecular N-H⋯O, N-H⋯Cl and O-H⋯Cl hydrogen bonds. Additional stabilization is provided by π-π stacking inter-actions between the benzene rings of the cations [centroid-centroid distances = 3.6962 (15) and 3.9340 (15) Å].

Related literature

For related structures of similar monoprotonated amines or imines, see: Bouacida (2008 ▶); Bouacida et al. (2005a ▶,b ▶,c ▶, 2009 ▶); Rademeyer (2004a ▶,b ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

(C7H10NO)2[SnCl6]

M = 579.73

Monoclinic,

a = 7.4785 (11) Å

b = 11.2959 (16) Å

c = 12.6153 (18) Å

β = 105.989 (5)°

V = 1024.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 2.04 mm−1

T = 100 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.423, T max = 0.693

5915 measured reflections

2279 independent reflections

2027 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.058

S = 1.07

2279 reflections

117 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −1.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811007252/hy2408sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007252/hy2408Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

(C7H10NO)2[SnCl6]	F(000) = 572
Mr = 579.73	Dx = 1.879 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 7.4785 (11) Å	Cell parameters from 3840 reflections
b = 11.2959 (16) Å	θ = 3.4–27.4°
c = 12.6153 (18) Å	µ = 2.04 mm−1
β = 105.989 (5)°	T = 100 K
V = 1024.5 (3) Å3	Block, colorless
Z = 2	0.20 × 0.18 × 0.16 mm

Bruker APEXII CCD diffractometer	2027 reflections with I > 2σ(I)
graphite	Rint = 0.038
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→5
Tmin = 0.423, Tmax = 0.693	k = −10→14
5915 measured reflections	l = −14→16
2279 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.058	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0194P)2 + 0.1921P] where P = (Fo2 + 2Fc2)/3
2279 reflections	(Δ/σ)max = 0.001
117 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −1.27 e Å−3

	x	y	z	Uiso*/Ueq
C1	0.8165 (3)	−0.12498 (19)	0.46444 (19)	0.0181 (5)
C2	0.7132 (3)	−0.06992 (19)	0.36967 (18)	0.0170 (5)
H2	0.6918	−0.1075	0.3017	0.02*
C3	0.6412 (3)	0.0428 (2)	0.37701 (19)	0.0186 (5)
C4	0.6736 (4)	0.0954 (2)	0.48072 (19)	0.0216 (5)
H4	0.6246	0.17	0.4867	0.026*
C5	0.7765 (4)	0.0391 (2)	0.5742 (2)	0.0249 (6)
H5	0.7973	0.0761	0.6424	0.03*
C6	0.8502 (3)	−0.0738 (2)	0.56723 (19)	0.0207 (5)
H6	0.9197	−0.1128	0.63	0.025*
C7	0.5266 (4)	0.1037 (2)	0.2755 (2)	0.0228 (5)
H7A	0.5162	0.0529	0.2121	0.027*
H7B	0.4023	0.1172	0.2826	0.027*
N1	0.8919 (3)	−0.24370 (17)	0.45477 (16)	0.0219 (4)
H1A	1.005	−0.2499	0.5014	0.033*
H1B	0.8986	−0.2547	0.3861	0.033*
H1C	0.8176	−0.2982	0.471	0.033*
O1	0.6072 (3)	0.21527 (14)	0.25759 (14)	0.0284 (4)
H1	0.5691	0.2678	0.2907	0.043*
Cl1	0.54335 (8)	0.34435 (5)	0.63534 (4)	0.01892 (13)
Cl2	0.29979 (8)	0.36720 (5)	0.36576 (4)	0.01874 (14)
Cl3	0.76854 (9)	0.43264 (5)	0.44207 (5)	0.02107 (14)
Sn1	0.5	0.5	0.5	0.01371 (8)

	U11	U22	U33	U12	U13	U23
C1	0.0175 (13)	0.0183 (11)	0.0200 (12)	0.0004 (10)	0.0073 (10)	0.0020 (9)
C2	0.0181 (13)	0.0167 (11)	0.0162 (11)	−0.0023 (10)	0.0049 (10)	−0.0015 (9)
C3	0.0171 (13)	0.0174 (11)	0.0218 (12)	−0.0041 (10)	0.0062 (10)	−0.0006 (10)
C4	0.0213 (13)	0.0194 (11)	0.0268 (13)	−0.0046 (11)	0.0112 (11)	−0.0042 (10)
C5	0.0268 (15)	0.0302 (13)	0.0207 (13)	−0.0091 (12)	0.0118 (11)	−0.0071 (11)
C6	0.0189 (13)	0.0266 (12)	0.0159 (12)	−0.0060 (11)	0.0037 (10)	0.0033 (10)
C7	0.0195 (14)	0.0179 (11)	0.0298 (14)	0.0007 (10)	0.0047 (11)	0.0037 (10)
N1	0.0216 (12)	0.0213 (10)	0.0240 (11)	0.0028 (9)	0.0083 (9)	0.0064 (8)
O1	0.0455 (13)	0.0152 (8)	0.0273 (10)	−0.0035 (9)	0.0144 (9)	−0.0013 (7)
Cl1	0.0239 (3)	0.0162 (3)	0.0145 (3)	−0.0011 (2)	0.0017 (2)	0.0028 (2)
Cl2	0.0234 (3)	0.0171 (3)	0.0138 (3)	−0.0036 (2)	0.0019 (2)	−0.0007 (2)
Cl3	0.0195 (3)	0.0229 (3)	0.0219 (3)	0.0023 (2)	0.0074 (2)	0.0003 (2)
Sn1	0.01617 (13)	0.01257 (12)	0.01161 (13)	0.00006 (8)	0.00251 (9)	−0.00002 (8)

C1—C6	1.378 (3)	C6—H6	0.93
C1—C2	1.380 (3)	C7—O1	1.441 (3)
C1—N1	1.473 (3)	C7—H7A	0.97
C2—C3	1.396 (3)	C7—H7B	0.97
C2—H2	0.93	N1—H1A	0.89
C3—C4	1.396 (3)	N1—H1B	0.89
C3—C7	1.498 (3)	N1—H1C	0.89
C4—C5	1.374 (4)	O1—H1	0.82
C4—H4	0.93	Sn1—Cl1	2.4097 (6)
C5—C6	1.401 (3)	Sn1—Cl2	2.4419 (6)
C5—H5	0.93	Sn1—Cl3	2.4402 (6)
C6—C1—C2	122.7 (2)	H7A—C7—H7B	107.9
C6—C1—N1	119.0 (2)	C1—N1—H1A	109.5
C2—C1—N1	118.3 (2)	C1—N1—H1B	109.5
C1—C2—C3	119.2 (2)	H1A—N1—H1B	109.5
C1—C2—H2	120.4	C1—N1—H1C	109.5
C3—C2—H2	120.4	H1A—N1—H1C	109.5
C4—C3—C2	118.7 (2)	H1B—N1—H1C	109.5
C4—C3—C7	121.1 (2)	C7—O1—H1	109.5
C2—C3—C7	120.2 (2)	Cl1—Sn1—Cl1i	180
C5—C4—C3	121.3 (2)	Cl1—Sn1—Cl3i	88.65 (2)
C5—C4—H4	119.4	Cl1i—Sn1—Cl3i	91.35 (2)
C3—C4—H4	119.4	Cl1—Sn1—Cl3	91.35 (2)
C4—C5—C6	120.3 (2)	Cl1i—Sn1—Cl3	88.65 (2)
C4—C5—H5	119.8	Cl3i—Sn1—Cl3	180
C6—C5—H5	119.8	Cl1—Sn1—Cl2i	91.13 (2)
C1—C6—C5	117.9 (2)	Cl1i—Sn1—Cl2i	88.87 (2)
C1—C6—H6	121.1	Cl3i—Sn1—Cl2i	89.93 (2)
C5—C6—H6	121.1	Cl3—Sn1—Cl2i	90.07 (2)
O1—C7—C3	111.7 (2)	Cl1—Sn1—Cl2	88.87 (2)
O1—C7—H7A	109.3	Cl1i—Sn1—Cl2	91.13 (2)
C3—C7—H7A	109.3	Cl3i—Sn1—Cl2	90.07 (2)
O1—C7—H7B	109.3	Cl3—Sn1—Cl2	89.93 (2)
C3—C7—H7B	109.3	Cl2i—Sn1—Cl2	180.000 (19)
C6—C1—C2—C3	0.8 (4)	C3—C4—C5—C6	−0.6 (4)
N1—C1—C2—C3	−179.7 (2)	C2—C1—C6—C5	−0.4 (4)
C1—C2—C3—C4	−1.1 (3)	N1—C1—C6—C5	−179.8 (2)
C1—C2—C3—C7	−179.2 (2)	C4—C5—C6—C1	0.2 (4)
C2—C3—C4—C5	1.0 (4)	C4—C3—C7—O1	60.8 (3)
C7—C3—C4—C5	179.1 (2)	C2—C3—C7—O1	−121.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl2	0.82	2.70	3.438 (2)	151
O1—H1···Cl3	0.82	2.79	3.370 (2)	130
N1—H1A···Cl3ii	0.89	2.64	3.298 (2)	131
N1—H1B···O1iii	0.89	1.83	2.721 (3)	175
N1—H1C···Cl1iv	0.89	2.71	3.338 (2)	128
N1—H1C···Cl2iv	0.89	2.57	3.304 (2)	140

CgI	CgJ	CgI···CgJ	β	CgI···PJ	slippage
Cg1	Cg1i	3.6962 (15)	25.82	-3.3272 (10)	1.610
Cg1	Cg1ii	3.9340 (15)	29.64	3.4194 (10)	1.945

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl2	0.82	2.70	3.438 (2)	151
O1—H1⋯Cl3	0.82	2.79	3.370 (2)	130
N1—H1A⋯Cl3i	0.89	2.64	3.298 (2)	131
N1—H1B⋯O1ii	0.89	1.83	2.721 (3)	175
N1—H1C⋯Cl1iii	0.89	2.71	3.338 (2)	128
N1—H1C⋯Cl2iii	0.89	2.57	3.304 (2)	140

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