Trimethyl­ammonium dichlorido­triphenyl­stannate(IV)

Diop, T.; Diop, L.; Jasinski, J.P.; Keeley, A.C.

doi:10.1107/S1600536812038457

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 10| October 2012| Page m1279

https://doi.org/10.1107/S1600536812038457

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Trimethylammonium dichloridotriphenylstannate(IV)

Tidiane Diop,^a ^* Libasse Diop,^a Jerry P. Jasinski ^b and Amanda C. Keeley ^b

^aLaboratoire de Chimie Minerale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and ^bDepartment of Chemistry, Keene State College 229 Main Street Keene, NH 03435-2001, USA
^*Correspondence e-mail: tijchimia@yahoo.fr

(Received 30 July 2012; accepted 7 September 2012; online 19 September 2012)

In the structure of the title monomeric coordination salt, (C₃H₁₀N)[Sn(C₆H₅)₃Cl₂], the Sn^IV atom is five coordinate, with the SnC₃Cl₂ entity in a trans trigonal–bipyramidal arrangement and the chlorine atoms in apical positions. In the crystal, the cations and anions are connected by N—H⋯Cl hydrogen bonds.

Related literature

For medical applications of tin(IV) compounds, see: Evans & Karpel (1985 ); Gielen (2002 ); Davies et al. (2008 ). For literature on organotin(IV) compounds, see: Chandrasekhar & Baskar (2003 ); Samuel et al. (2002 ); Nath et al. (2003 ). For related structures, see: Ng (1999 , 1995 ); Harrison et al. (1978 ); Nayek et al. (2010 ); Sow et al. (2012 ); De Lorentiis et al. (2011 ).

Experimental

Crystal data

(C₃H₁₀N)[Sn(C₆H₅)Cl₂]
M_r = 481.01
Monoclinic, P 2₁ /n
a = 9.2650 (2) Å
b = 15.6882 (4) Å
c = 14.7891 (3) Å
β = 90.941 (2)°
V = 2149.32 (8) Å³
Z = 4
Cu Kα radiation
μ = 11.75 mm⁻¹
T = 173 K
0.34 × 0.22 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.328, T_max = 1.000
13300 measured reflections
4143 independent reflections
3739 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.083
S = 1.06
4143 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.53 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl1ⁱ	0.91	2.21	3.087 (3)	161
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, I-2, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S1600536812038457/pk2438sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038457/pk2438Isup2.hkl

checkCIF report

Comment top

The interest in synthesis of new organotin(IV) derivatives is related to their applications in different fields (agrochemicals, surface disinfectants and marine antifouling paints) (Evans & Karpel, 1985; Gielen, 2002; Davies et al., 2008) and explains the involvement of many groups in the search for new organotin compounds (Chandrasekhar & Baskar, 2003; Samuel et al., 2002; Nath et al., 2003). Many compounds containing the [SnPh₃Cl₂]^- ion in the trans conformation have been reported (Ng, 1995, 1999; Harrison et al., 1978; Nayek et al., 2010; Sow et al., 2012). In our search for new organotin(IV) compounds we have initiated here the study of the interactions between (CH₃)₃N.HCl and SnPh₃Cl, which led to the title compound. In the [SnPh₃Cl₂]^- anion, the tin atom is located on a centre of inversion and is bonded to two Cl atoms and three phenyl groups giving a trigonal bipyramidal geometry with the chloride atoms in trans-positions (Fig. 1). The sum of the angles at atom Sn by the ipso-carbons [128.08 (12)°, 113.70 (12)°, 117.83 (12)°] is 359.61°. The corresponding axial Cl₁—Sn—Cl₂ angle is 171.62 (3)°, indicating a slight deviation from linearity. The Sn—C bond distances (2.135 (3) Å, 2.142 (3) Å and 2.151 (3) Å) are similar to those reported for bis(triphenylphosphanylidene)iminium dichloridotriphenylstannate(IV) (2.134 (3) Å, 2.1476 (19) Å and 2.1476 (19) Å) (De Lorentiis et al., 2011). The two axial Sn—Cl distances, [Sn—Cl 2.5227 (7) Å and 2.6983 (8) Å], are very close to those reported (Sow et al., 2012). The two types of Sn—Cl binding are due to disruption of NH ··· Cl hydrogen bonding on one of the chlorine atoms. The C–N–C angles of the cation are close to 109°, in agreement with the expected sp³ hybridization. The cation and the anion are connected by N—H···.Cl hydrogen bonds (Fig. 2).

Related literature top

For medical applications of tin(IV) compounds, see: Evans & Karpel (1985); Gielen (2002); Davies et al. (2008). For literature on new organotin(IV) compounds, see: Chandrasekhar & Baskar (2003); Samuel et al. (2002); Nath et al. (2003). For related structures, see: Ng (1999, 1995); Harrison et al. (1978); Nayek et al. (2010); Sow et al. (2012); De Lorentiis et al. (2011).

Experimental top

Crystals of the title compound, [C₃H₁₀N⁺] [Sn(C₆H₅)₃Cl₂^-], were obtained by reacting SnPh₃Cl with (CH₃)₃N.HCl in ethanol in a 1/1 ratio. (CH₃)₃N.HCl (Merck) and SnPh₃Cl (Aldrich) were used without further purification. The title compound was obtained by mixing in a 1/1 ratio (CH₃)₃N.HCl dissolved in methanol and a minimum of water and SnPh₃Cl dissolved in methanol. The mixture was stirred for around two hours at room temperature and upon slow solvent evaporation gave prismatic crystals suitable for X-ray diffraction analysis.

Structure description top

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. : Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. : The packing of the structure viewed along the c axis. N—H···Cl hydrogen bonds are shown as dashed lines. The remaining H atoms have been removed for clarity.

Trimethylammonium dichloridotriphenylstannate(IV) top

Crystal data top

(C₃H₁₀N)[Sn(C₆H₅)Cl₂]	F(000) = 968
M_r = 481.01	D_x = 1.486 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2yn	Cell parameters from 6465 reflections
a = 9.2650 (2) Å	θ = 3.0–71.4°
b = 15.6882 (4) Å	µ = 11.75 mm⁻¹
c = 14.7891 (3) Å	T = 173 K
β = 90.941 (2)°	Chunk, colorless
V = 2149.32 (8) Å³	0.34 × 0.22 × 0.16 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4143 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3739 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
Detector resolution: 16.15 pixels mm^-1	θ_max = 71.6°, θ_min = 4.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Oxford Diffraction, 2010)	k = 0→19
T_min = 0.328, T_max = 1.000	l = 0→17
13300 measured 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0407P)² + 0.8952P] where P = (F_o² + 2F_c²)/3
4143 reflections	(Δ/σ)_max = 0.002
229 parameters	Δρ_max = 0.53 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

(C₃H₁₀N)[Sn(C₆H₅)Cl₂]	V = 2149.32 (8) Å³
M_r = 481.01	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 9.2650 (2) Å	µ = 11.75 mm⁻¹
b = 15.6882 (4) Å	T = 173 K
c = 14.7891 (3) Å	0.34 × 0.22 × 0.16 mm
β = 90.941 (2)°

Data collection top

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4143 independent reflections
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Oxford Diffraction, 2010)	3739 reflections with I > 2σ(I)
T_min = 0.328, T_max = 1.000	R_int = 0.054
13300 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.083	H-atom parameters constrained
S = 1.06	Δρ_max = 0.53 e Å⁻³
4143 reflections	Δρ_min = −0.53 e Å⁻³
229 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
Sn1	0.25216 (2)	0.438102 (12)	0.741033 (13)	0.01599 (8)
Cl1	0.34357 (9)	0.51960 (5)	0.59185 (5)	0.02688 (18)
Cl2	0.18198 (9)	0.34254 (5)	0.87027 (5)	0.02576 (18)
N1	0.3823 (3)	0.37067 (17)	0.38252 (19)	0.0258 (6)
H1	0.4476	0.4132	0.3918	0.031*
C1	0.1366 (3)	0.5479 (2)	0.7884 (2)	0.0208 (7)
C2	0.1101 (4)	0.6179 (2)	0.7323 (2)	0.0288 (8)
H2	0.1510	0.6199	0.6738	0.035*
C3	0.0234 (4)	0.6853 (2)	0.7619 (3)	0.0358 (9)
H3	0.0051	0.7324	0.7231	0.043*
C4	−0.0352 (5)	0.6838 (2)	0.8462 (3)	0.0402 (10)
H4	−0.0947	0.7294	0.8654	0.048*
C5	−0.0079 (5)	0.6165 (3)	0.9030 (3)	0.0481 (12)
H5	−0.0469	0.6159	0.9620	0.058*
C6	0.0780 (5)	0.5481 (2)	0.8737 (3)	0.0369 (9)
H6	0.0960	0.5014	0.9132	0.044*
C7	0.1311 (3)	0.36151 (19)	0.64762 (19)	0.0174 (6)
C8	0.0298 (4)	0.4005 (2)	0.5905 (2)	0.0276 (7)
H8	0.0208	0.4608	0.5908	0.033*
C9	−0.0578 (4)	0.3526 (3)	0.5332 (2)	0.0404 (10)
H9	−0.1287	0.3799	0.4962	0.048*
C10	−0.0417 (5)	0.2640 (3)	0.5299 (3)	0.0459 (11)
H10	−0.0998	0.2309	0.4897	0.055*
C11	0.0582 (5)	0.2257 (3)	0.5850 (3)	0.0434 (10)
H11	0.0697	0.1655	0.5827	0.052*
C12	0.1433 (4)	0.2732 (2)	0.6441 (2)	0.0287 (8)
H12	0.2108	0.2451	0.6828	0.034*
C13	0.4751 (3)	0.42610 (19)	0.7796 (2)	0.0203 (7)
C14	0.5815 (4)	0.4029 (2)	0.7194 (3)	0.0314 (8)
H14	0.5568	0.3940	0.6575	0.038*
C15	0.7231 (4)	0.3926 (3)	0.7486 (3)	0.0469 (11)
H15	0.7940	0.3747	0.7070	0.056*
C16	0.7619 (5)	0.4079 (3)	0.8363 (4)	0.0518 (12)
H16	0.8597	0.4017	0.8553	0.062*
C17	0.6597 (5)	0.4321 (3)	0.8969 (4)	0.0592 (14)
H17	0.6867	0.4428	0.9582	0.071*
C18	0.5153 (4)	0.4413 (3)	0.8688 (3)	0.0416 (10)
H18	0.4446	0.4581	0.9111	0.050*
C19	0.4022 (6)	0.3087 (3)	0.4570 (3)	0.0486 (12)
H19A	0.3296	0.2635	0.4512	0.073*
H19B	0.3913	0.3378	0.5151	0.073*
H19C	0.4989	0.2837	0.4540	0.073*
C20	0.4135 (6)	0.3326 (3)	0.2933 (3)	0.0504 (11)
H20A	0.5078	0.3043	0.2960	0.076*
H20B	0.4149	0.3776	0.2473	0.076*
H20C	0.3386	0.2908	0.2775	0.076*
C21	0.2380 (4)	0.4099 (3)	0.3837 (3)	0.0465 (11)
H21A	0.1643	0.3652	0.3835	0.070*
H21B	0.2248	0.4460	0.3301	0.070*
H21C	0.2290	0.4448	0.4383	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01316 (13)	0.01873 (12)	0.01599 (12)	−0.00260 (7)	−0.00193 (8)	−0.00006 (7)
Cl1	0.0250 (4)	0.0310 (4)	0.0247 (4)	−0.0069 (3)	0.0019 (3)	0.0076 (3)
Cl2	0.0272 (4)	0.0299 (4)	0.0201 (4)	−0.0032 (3)	−0.0008 (3)	0.0082 (3)
N1	0.0266 (16)	0.0215 (13)	0.0292 (15)	−0.0046 (12)	0.0047 (12)	−0.0017 (11)
C1	0.0162 (16)	0.0226 (15)	0.0236 (17)	−0.0008 (12)	−0.0050 (13)	−0.0098 (12)
C2	0.033 (2)	0.0266 (17)	0.0270 (18)	0.0065 (15)	−0.0098 (15)	−0.0050 (14)
C3	0.039 (2)	0.0297 (19)	0.038 (2)	0.0097 (16)	−0.0127 (18)	−0.0103 (15)
C4	0.038 (2)	0.0291 (19)	0.054 (3)	0.0014 (16)	0.005 (2)	−0.0202 (17)
C5	0.062 (3)	0.038 (2)	0.045 (2)	−0.007 (2)	0.030 (2)	−0.0145 (18)
C6	0.056 (3)	0.0246 (17)	0.031 (2)	−0.0022 (17)	0.0143 (18)	−0.0039 (15)
C7	0.0150 (15)	0.0246 (15)	0.0127 (14)	−0.0037 (12)	0.0012 (11)	−0.0020 (11)
C8	0.0255 (19)	0.0328 (18)	0.0243 (17)	−0.0009 (14)	−0.0011 (14)	0.0038 (14)
C9	0.027 (2)	0.069 (3)	0.0252 (19)	−0.0121 (19)	−0.0130 (15)	0.0065 (18)
C10	0.048 (3)	0.062 (3)	0.027 (2)	−0.030 (2)	−0.0060 (18)	−0.0113 (19)
C11	0.062 (3)	0.034 (2)	0.035 (2)	−0.018 (2)	−0.001 (2)	−0.0107 (17)
C12	0.033 (2)	0.0268 (17)	0.0266 (18)	0.0011 (15)	−0.0024 (15)	−0.0019 (14)
C13	0.0119 (15)	0.0214 (15)	0.0276 (18)	−0.0009 (12)	−0.0016 (13)	0.0015 (12)
C14	0.0238 (19)	0.0297 (18)	0.041 (2)	0.0000 (14)	0.0016 (16)	0.0007 (15)
C15	0.020 (2)	0.047 (3)	0.073 (3)	0.0009 (18)	0.009 (2)	0.016 (2)
C16	0.019 (2)	0.057 (3)	0.078 (4)	−0.0007 (19)	−0.014 (2)	0.020 (3)
C17	0.038 (3)	0.089 (4)	0.049 (3)	−0.009 (2)	−0.028 (2)	0.006 (2)
C18	0.024 (2)	0.065 (3)	0.036 (2)	−0.0048 (18)	−0.0083 (17)	−0.0027 (18)
C19	0.075 (4)	0.033 (2)	0.037 (2)	0.008 (2)	0.007 (2)	0.0056 (17)
C20	0.061 (3)	0.058 (3)	0.032 (2)	0.009 (2)	0.013 (2)	−0.004 (2)
C21	0.030 (2)	0.055 (3)	0.054 (3)	0.004 (2)	−0.0066 (19)	−0.016 (2)

Geometric parameters (Å, º) top

Sn1—C7	2.135 (3)	C10—C11	1.363 (6)
Sn1—C13	2.142 (3)	C10—H10	0.9500
Sn1—C1	2.151 (3)	C11—C12	1.385 (5)
Sn1—Cl2	2.5227 (7)	C11—H11	0.9500
Sn1—Cl1	2.6983 (8)	C12—H12	0.9500
N1—C21	1.472 (5)	C13—C18	1.385 (5)
N1—C19	1.478 (5)	C13—C14	1.388 (5)
N1—C20	1.481 (5)	C14—C15	1.384 (5)
N1—H1	0.9099	C14—H14	0.9500
C1—C6	1.381 (5)	C15—C16	1.361 (7)
C1—C2	1.396 (5)	C15—H15	0.9500
C2—C3	1.403 (5)	C16—C17	1.369 (7)
C2—H2	0.9500	C16—H16	0.9500
C3—C4	1.368 (6)	C17—C18	1.403 (6)
C3—H3	0.9500	C17—H17	0.9500
C4—C5	1.370 (6)	C18—H18	0.9500
C4—H4	0.9500	C19—H19A	0.9800
C5—C6	1.409 (5)	C19—H19B	0.9800
C5—H5	0.9500	C19—H19C	0.9800
C6—H6	0.9500	C20—H20A	0.9800
C7—C12	1.391 (5)	C20—H20B	0.9800
C7—C8	1.394 (4)	C20—H20C	0.9800
C8—C9	1.385 (5)	C21—H21A	0.9800
C8—H8	0.9500	C21—H21B	0.9800
C9—C10	1.399 (6)	C21—H21C	0.9800
C9—H9	0.9500

C7—Sn1—C13	128.08 (12)	C11—C10—H10	120.3
C7—Sn1—C1	113.70 (12)	C9—C10—H10	120.3
C13—Sn1—C1	117.83 (12)	C10—C11—C12	120.9 (4)
C7—Sn1—Cl2	90.95 (8)	C10—C11—H11	119.6
C13—Sn1—Cl2	90.30 (9)	C12—C11—H11	119.6
C1—Sn1—Cl2	95.35 (10)	C11—C12—C7	120.9 (3)
C7—Sn1—Cl1	84.62 (8)	C11—C12—H12	119.5
C13—Sn1—Cl1	86.86 (9)	C7—C12—H12	119.5
C1—Sn1—Cl1	92.95 (10)	C18—C13—C14	118.3 (3)
Cl2—Sn1—Cl1	171.62 (3)	C18—C13—Sn1	118.8 (3)
C21—N1—C19	111.6 (3)	C14—C13—Sn1	122.9 (3)
C21—N1—C20	111.7 (3)	C15—C14—C13	120.6 (4)
C19—N1—C20	112.0 (3)	C15—C14—H14	119.7
C21—N1—H1	107.0	C13—C14—H14	119.7
C19—N1—H1	107.2	C16—C15—C14	120.7 (4)
C20—N1—H1	107.0	C16—C15—H15	119.6
C6—C1—C2	118.2 (3)	C14—C15—H15	119.6
C6—C1—Sn1	120.3 (3)	C15—C16—C17	119.9 (4)
C2—C1—Sn1	121.3 (3)	C15—C16—H16	120.0
C1—C2—C3	120.2 (4)	C17—C16—H16	120.0
C1—C2—H2	119.9	C16—C17—C18	120.0 (5)
C3—C2—H2	119.9	C16—C17—H17	120.0
C4—C3—C2	120.7 (4)	C18—C17—H17	120.0
C4—C3—H3	119.7	C13—C18—C17	120.4 (4)
C2—C3—H3	119.7	C13—C18—H18	119.8
C3—C4—C5	120.0 (4)	C17—C18—H18	119.8
C3—C4—H4	120.0	N1—C19—H19A	109.5
C5—C4—H4	120.0	N1—C19—H19B	109.5
C4—C5—C6	119.8 (4)	H19A—C19—H19B	109.5
C4—C5—H5	120.1	N1—C19—H19C	109.5
C6—C5—H5	120.1	H19A—C19—H19C	109.5
C1—C6—C5	121.0 (4)	H19B—C19—H19C	109.5
C1—C6—H6	119.5	N1—C20—H20A	109.5
C5—C6—H6	119.5	N1—C20—H20B	109.5
C12—C7—C8	117.9 (3)	H20A—C20—H20B	109.5
C12—C7—Sn1	122.9 (2)	N1—C20—H20C	109.5
C8—C7—Sn1	119.1 (2)	H20A—C20—H20C	109.5
C9—C8—C7	121.0 (3)	H20B—C20—H20C	109.5
C9—C8—H8	119.5	N1—C21—H21A	109.5
C7—C8—H8	119.5	N1—C21—H21B	109.5
C8—C9—C10	119.9 (4)	H21A—C21—H21B	109.5
C8—C9—H9	120.1	N1—C21—H21C	109.5
C10—C9—H9	120.1	H21A—C21—H21C	109.5
C11—C10—C9	119.3 (3)	H21B—C21—H21C	109.5

C7—Sn1—C1—C6	103.1 (3)	C12—C7—C8—C9	1.2 (5)
C13—Sn1—C1—C6	−83.4 (3)	Sn1—C7—C8—C9	−175.6 (3)
Cl2—Sn1—C1—C6	9.7 (3)	C7—C8—C9—C10	−2.3 (6)
Cl1—Sn1—C1—C6	−171.4 (3)	C8—C9—C10—C11	1.5 (6)
C7—Sn1—C1—C2	−72.4 (3)	C9—C10—C11—C12	0.3 (7)
C13—Sn1—C1—C2	101.0 (3)	C10—C11—C12—C7	−1.3 (6)
Cl2—Sn1—C1—C2	−165.8 (3)	C8—C7—C12—C11	0.6 (5)
Cl1—Sn1—C1—C2	13.0 (3)	Sn1—C7—C12—C11	177.3 (3)
C6—C1—C2—C3	−1.5 (5)	C7—Sn1—C13—C18	−142.3 (3)
Sn1—C1—C2—C3	174.2 (3)	C1—Sn1—C13—C18	45.3 (3)
C1—C2—C3—C4	0.7 (6)	Cl2—Sn1—C13—C18	−50.9 (3)
C2—C3—C4—C5	0.7 (6)	Cl1—Sn1—C13—C18	137.0 (3)
C3—C4—C5—C6	−1.3 (7)	C7—Sn1—C13—C14	37.0 (3)
C2—C1—C6—C5	0.9 (6)	C1—Sn1—C13—C14	−135.3 (3)
Sn1—C1—C6—C5	−174.8 (3)	Cl2—Sn1—C13—C14	128.5 (3)
C4—C5—C6—C1	0.4 (7)	Cl1—Sn1—C13—C14	−43.6 (3)
C13—Sn1—C7—C12	42.1 (3)	C18—C13—C14—C15	2.1 (5)
C1—Sn1—C7—C12	−145.3 (3)	Sn1—C13—C14—C15	−177.3 (3)
Cl2—Sn1—C7—C12	−49.0 (3)	C13—C14—C15—C16	−2.3 (6)
Cl1—Sn1—C7—C12	123.8 (3)	C14—C15—C16—C17	1.2 (7)
C13—Sn1—C7—C8	−141.3 (2)	C15—C16—C17—C18	0.0 (8)
C1—Sn1—C7—C8	31.3 (3)	C14—C13—C18—C17	−0.9 (6)
Cl2—Sn1—C7—C8	127.6 (2)	Sn1—C13—C18—C17	178.5 (3)
Cl1—Sn1—C7—C8	−59.6 (2)	C16—C17—C18—C13	−0.1 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.91	2.21	3.087 (3)	161

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	(C₃H₁₀N)[Sn(C₆H₅)Cl₂]
M_r	481.01
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	173
a, b, c (Å)	9.2650 (2), 15.6882 (4), 14.7891 (3)
β (°)	90.941 (2)
V (Å³)	2149.32 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	11.75
Crystal size (mm)	0.34 × 0.22 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur Eos Gemini
Absorption correction	Multi-scan (CrysAlis PRO and CrysAlis RED; Oxford Diffraction, 2010)
T_min, T_max	0.328, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	13300, 4143, 3739
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.615

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.083, 1.06
No. of reflections	4143
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.53

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl1ⁱ	0.91	2.21	3.087 (3)	160.7

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

JPJ acknowledges the NSF–MRI program (grant No. CHE1039027) for funds to purchase the X-ray diffractometer.

References

Chandrasekhar, V. & Baskar, V. (2003). Indian J. Chem. Sect. A Inorg. Bio-inorg. Phys. Theor. Anal. Chem. 42, 2376–2381. Google Scholar
Davies, A. G., Gielen, M., Pannell, K. H. & Tiekink, E. R. T. (2008). Editors. Tin Chemistry. Chichester: Wiley. Google Scholar
De Lorentiis, L., Graiff, C. & Predieri, G. (2011). Acta Cryst. E67, m1356. Web of Science CSD CrossRef IUCr Journals Google Scholar
Evans, C. J. & Karpel, S. (1985). Organotin Compounds in Modern Technology, J. Organomet. Chem. Library, Vol. 16. Amsterdam: Elsevier. Google Scholar
Gielen, M. (2002). Appl. Organomet. Chem. 16, 481–494. Web of Science CrossRef CAS Google Scholar
Harrison, P. G., Molloy, K., Phillips, R. C., Smith, P. J. & Crowe, A. J. (1978). J. Organomet. Chem. 160, 421–434. CSD CrossRef CAS Web of Science Google Scholar
Nath, M., Pokharia, S., Song, X., Eng, G., Gielen, M., Kemmer, M., Biesemans, M., Willem, R. & Vos, D. D. (2003). Appl. Organomet. Chem. 17, 305–314. Web of Science CrossRef CAS Google Scholar
Nayek, H. P., Massa, W. & Dehnen, S. (2010). Inorg. Chem. 49, 144–149. Web of Science CSD CrossRef CAS PubMed Google Scholar
Ng, S. W. (1995). Acta Cryst. C51, 1124–1125. CSD CrossRef Web of Science IUCr Journals Google Scholar
Ng, S. W. (1999). Acta Cryst. C55, 523–531. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England. Google Scholar
Samuel, P. M., De Vos, D., Raveendra, D., Sarma, J. A. R. P. & Roy, S. (2002). Bioorg. Med. Chem. Lett. 12, 61–64. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sow, Y., Diop, L., Kociok-Kohn, G. & Molloy, K. C. (2012). Acta Cryst. E68, m1015–m1016. CSD CrossRef IUCr Journals Google Scholar