Trimethyl-ammonium dichlorido-triphenyl-stannate(IV).

In the structure of the title monomeric coordination salt, (C(3)H(10)N)[Sn(C(6)H(5))(3)Cl(2)], the Sn(IV) atom is five coordinate, with the SnC(3)Cl(2) 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 = 481.01

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.083

S = 1.06

4143 reflections

229 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.53 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis n class="Disease">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.

Crystal structure: contains datablock(s) I, I-2, New_Global_Publ_Block. DOI: 10.1107/S1600536812038457/pk2438sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038457/pk2438Isup2.hkl

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

(C3H10N)[Sn(C6H5)Cl2]	F(000) = 968
Mr = 481.01	Dx = 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

Oxford Diffraction Xcalibur Eos Gemini diffractometer	4143 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3739 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.054
Detector resolution: 16.15 pixels mm-1	θmax = 71.6°, θmin = 4.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Oxford Diffraction, 2010)	k = 0→19
Tmin = 0.328, Tmax = 1.000	l = 0→17
13300 measured 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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.083	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0407P)2 + 0.8952P] where P = (Fo2 + 2Fc2)/3
4143 reflections	(Δ/σ)max = 0.002
229 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.53 e Å−3

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	0.25216 (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*

	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)

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)

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

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) .