Bis(3-hy­droxy­methyl­anilinium) hexa­chloridostannate(IV)

Bouacida, S.; Kechout, H.; Belhouas, R.; Merazig, H.; Roisnel, T.

doi:10.1107/S1600536811007252

metal-organic compounds

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Volume 67| Part 4| April 2011| Page m395

doi:10.1107/S1600536811007252

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Bis(3-hydroxymethylanilinium) hexachloridostannate(IV)

Sofiane Bouacida,^a,^b ^* Habiba Kechout,^a Ratiba Belhouas,^a Hocine Merazig ^a and Thierry Roisnel ^c

^aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, 25000 Algeria, ^bDépartement Sciences de la Matière, Facult des Sciences Exactes et Sciences de la Nature et de la Vie, Université Larbi Ben M'hidi, Oum El Bouaghi 04000, Algeria, and ^cCentre de Difractométrie X, UMR 6226 CNRS Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
^*Correspondence e-mail: bouacida_sofiane@yahoo.fr

(Received 18 February 2011; accepted 25 February 2011; online 2 March 2011)

In the title compound, (C₇H₁₀NO)₂[SnCl₆], the Sn^IV atom, located on an inversion center, exists in an octahedral coordination environment. The crystal structure exhibits alternating organic and inorganic layers parallel to ( $[\overline{1}]$ 01). The cations and anions are linked via intermolecular N—H⋯O, N—H⋯Cl and O—H⋯Cl hydrogen bonds. Additional stabilization is provided by π–π stacking interactions 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_r = 579.73
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.025
wR(F²) = 0.058
S = 1.07
2279 reflections
117 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −1.27 e Å⁻³

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) -x+2, -y, -z+1; (ii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

The title compound was prepared as part of our ongoing studies of hydrogen-bonding interactions in the crystal structures of protonated amines (Bouacida, 2008; Bouacida et al., 2009).

In the title compound (Fig. 1), all bond distances and angles are within the ranges of accepted values (CSD, Allen, 2002). The amino N atom is protonated as in the other amines and imines (Bouacida et al., 2005a,b,c; Rademeyer, 2004a,b). The Sn^IV atom is six-coordinated with six Cl atoms, located on an inversion center, forming a slightly distorted octahedral geometry. The crystal structure can be described as alternating layers of [SnCl₆]^2- comlpex anions and 3-hydroxymethylanilinium cations parallel to (1 0 1) (Fig. 2). In the crystal, the components of the structure are linked via intermolecular N—H···O, N—H···Cl and O—H···Cl hydrogen bonds (Table 1, Fig. 3). Additional stabilization is provided by π–π stacking interactions (Table 2). These interactions link the cations and anions together, reinforcing the cohesion of the ionic structure.

Related literature top

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 top

Crystals of the title compound were grown from an aqueous solution that was obtained by dissolving SnCl₂ (1 mmol) and 3-aminophenylmethanol (2 mmol) in hydrochloric acid. The solution was slowly evaporated to dryness for a couple of weeks. Some colorless crystals were carefully isolated under polarizing microscope for X-ray diffraction analysis.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).

Figures top

	Fig. 1. Molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. [Symmetry code: (i) 1-x, 1-y, 1-z.]
	Fig. 2. A diagram of the layered crystal packing in the title compound, viewed down the b axis, showing alternating layers of octahedral anions and cations.
	Fig. 3. Crystal packing of the title compound, viewed down the a axis, showing hydrogen bonds (dashed lines). H atoms not involved in hydrogen bonds have been omitted for clarity.

Bis(3-hydroxymethylanilinium) hexachloridostannate(IV) top

Crystal data top

(C₇H₁₀NO)₂[SnCl₆]	F(000) = 572
M_r = 579.73	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	2027 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→5
T_min = 0.423, T_max = 0.693	k = −10→14
5915 measured reflections	l = −14→16
2279 independent reflections

Refinement top

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(F_o²) + (0.0194P)² + 0.1921P] where P = (F_o² + 2F_c²)/3
2279 reflections	(Δ/σ)_max = 0.001
117 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −1.27 e Å⁻³

Crystal data top

(C₇H₁₀NO)₂[SnCl₆]	V = 1024.5 (3) Å³
M_r = 579.73	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.4785 (11) Å	µ = 2.04 mm⁻¹
b = 11.2959 (16) Å	T = 100 K
c = 12.6153 (18) Å	0.20 × 0.18 × 0.16 mm
β = 105.989 (5)°

Data collection top

Bruker APEXII CCD diffractometer	2279 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2027 reflections with I > 2σ(I)
T_min = 0.423, T_max = 0.693	R_int = 0.038
5915 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.07	Δρ_max = 0.63 e Å⁻³
2279 reflections	Δρ_min = −1.27 e Å⁻³
117 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

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···Cl1^iv	0.89	2.71	3.338 (2)	128
N1—H1C···Cl2^iv	0.89	2.57	3.304 (2)	140

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

Experimental details

Crystal data
Chemical formula	(C₇H₁₀NO)₂[SnCl₆]
M_r	579.73
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	7.4785 (11), 11.2959 (16), 12.6153 (18)
β (°)	105.989 (5)
V (Å³)	1024.5 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.04
Crystal size (mm)	0.20 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.423, 0.693
No. of measured, independent and observed [I > 2σ(I)] reflections	5915, 2279, 2027
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.058, 1.07
No. of reflections	2279
No. of parameters	117
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −1.27

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR2002 (Burla et al., 2003), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg & Berndt, 1999), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) −x+2, −y, −z+1; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y, −z+1.

Table 2. π–π stacking interactions (Å,°) top

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

Symmetry codes: (i) -x,-y,1-z; (ii) 1-x,-y,1-z. Notes: Cg1 is the centroid of the C1–C6 ring; CgI···CgJ is the distance between the centroids; CgI···PJ is the perpendicular distance of CgI on ring plane J; β is the angle between the vector CgI—CgJ and the normal to ring plane I; slippage is the distance between CgI and the projection of CgJ on ring plane I.

Acknowledgements

This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Mentouri-Constantine, Algeria.

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