Butyl-trichlorido{2-[(diisopropyl-ammonio)-meth-yl]phen-yl}tin(IV) dichloro-methane monosolvate.

The title compound, [Sn(C(4)H(9))(C(13)H(21)N)Cl(3)]·CH(2)Cl(2), was obtained by recrystallization of [2-(diisopropyl-amino-meth-yl)phen-yl]tin(IV) butyl dichloride from a CH(2)Cl(2)/n-hexane mixture (1:4 v/v) in the presence of ambient moisture. Partial hydrolysis led to the title compound, the hydro-chloric acid adduct of the dichloride, having a penta-coordinated Sn atom with a trigonal-bipyramidal C(2)SnCl(3) core. The N atom of the 2-[(diisopropyl-ammonio)-meth-yl]phenyl ligand forms a strong intra-molecular N-H⋯Cl hydrogen bond, resulting in a zwitterionic species, [2-((i)Pr(2)HN(+)CH(2))C(6)H(4)]SnBuCl(3) (-)·CH(2)Cl(2). Disorder was found in the n-butyl group, which was refined as disordered over three positions, with site occupancies of 0.22 (1), 0.51 (1) and 0.27 (2).

Related literature

For related tin(IV) compounds, see: Varga et al. (2001 ▶, 2005 ▶, 2006 ▶); Varga & Silvestru (2007 ▶); Rotar et al. (2007 ▶, 2009 ▶); Rotar, Schuermann et al. (2008 ▶); Rotar, Varga & Silvestru (2008 ▶); Švec et al. (2010 ▶).

Experimental

Crystal data

[Sn(C4H9)(C13H21N)Cl3]·CH2Cl2

M = 558.39

Triclinic,

a = 10.654 (8) Å

b = 11.093 (9) Å

c = 12.406 (10) Å

α = 115.594 (13)°

β = 100.767 (15)°

γ = 97.176 (15)°

V = 1263.5 (17) Å3

Z = 2

Mo Kα radiation

μ = 1.54 mm−1

T = 297 K

0.45 × 0.20 × 0.18 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (Bruker, 2000 ▶) T min = 0.544, T max = 0.769

9126 measured reflections

4416 independent reflections

3122 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.213

S = 1.02

4416 reflections

257 parameters

40 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.43 e Å−3

Δρmin = −0.73 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810050713/zl2332sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050713/zl2332Isup2.hkl

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

[Sn(C4H9)(C13H21N)Cl3]·CH2Cl2	Z = 2
Mr = 558.39	F(000) = 564
Triclinic, P1	Dx = 1.468 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.654 (8) Å	Cell parameters from 1665 reflections
b = 11.093 (9) Å	θ = 2.4–20.1°
c = 12.406 (10) Å	µ = 1.54 mm−1
α = 115.594 (13)°	T = 297 K
β = 100.767 (15)°	Block, colourless
γ = 97.176 (15)°	0.45 × 0.20 × 0.18 mm
V = 1263.5 (17) Å3

Bruker SMART APEX CCD area-detector diffractometer	4416 independent reflections
Radiation source: fine-focus sealed tube	3122 reflections with I > 2σ(I)
graphite	Rint = 0.074
phi and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (Bruker, 2000)	h = −12→12
Tmin = 0.544, Tmax = 0.769	k = −13→13
9126 measured reflections	l = −14→14

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.213	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.1038P)2 + 0.0754P] where P = (Fo2 + 2Fc2)/3
4416 reflections	(Δ/σ)max = 0.008
257 parameters	Δρmax = 1.43 e Å−3
40 restraints	Δρmin = −0.73 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	Occ. (<1)
C1	0.4960 (8)	0.7632 (8)	0.8171 (7)	0.0490 (19)
C2	0.4078 (8)	0.8089 (8)	0.8876 (7)	0.052 (2)
C3	0.4102 (10)	0.7820 (10)	0.9900 (7)	0.068 (3)
H3	0.3545	0.8145	1.0401	0.082*
C4	0.4950 (11)	0.7076 (11)	1.0147 (9)	0.079 (3)
H4	0.4942	0.6882	1.0804	0.095*
C5	0.5813 (11)	0.6613 (11)	0.9442 (10)	0.080 (3)
H5	0.6392	0.6124	0.9626	0.096*
C6	0.5798 (10)	0.6891 (10)	0.8458 (9)	0.070 (3)
H6	0.6369	0.6570	0.7973	0.084*
C7	0.3141 (8)	0.8942 (8)	0.8704 (7)	0.054 (2)
H7A	0.3545	0.9547	0.8424	0.065*
H7B	0.2999	0.9514	0.9501	0.065*
C8	0.1153 (9)	0.6964 (9)	0.7985 (8)	0.061 (2)
H8	0.1822	0.6500	0.8175	0.073*
C9	0.0569 (11)	0.7551 (12)	0.9098 (10)	0.093 (3)
H9A	0.1267	0.8024	0.9852	0.139*
H9B	0.0012	0.6814	0.9118	0.139*
H9C	0.0064	0.8181	0.9019	0.139*
C10	0.0112 (9)	0.5909 (11)	0.6802 (9)	0.084 (3)
H10A	−0.0587	0.6325	0.6632	0.126*
H10B	−0.0232	0.5140	0.6910	0.126*
H10C	0.0501	0.5602	0.6119	0.126*
C11	0.0904 (9)	0.8991 (10)	0.7562 (8)	0.067 (2)
H11	0.0007	0.8537	0.7457	0.080*
C12	0.1211 (12)	1.0427 (11)	0.8664 (10)	0.098 (4)
H12A	0.1148	1.0351	0.9395	0.147*
H12B	0.0593	1.0926	0.8498	0.147*
H12C	0.2084	1.0905	0.8791	0.147*
C13	0.0929 (13)	0.9059 (15)	0.6384 (10)	0.109 (4)
H13A	0.0260	0.9499	0.6199	0.163*
H13B	0.0769	0.8145	0.5716	0.163*
H13C	0.1773	0.9575	0.6483	0.163*
C14	0.571 (6)	0.712 (5)	0.490 (3)	0.065 (6)	0.22
H14A	0.5530	0.6136	0.4589	0.078*	0.22
H14B	0.5079	0.7296	0.4342	0.078*	0.22
C15	0.702 (6)	0.754 (8)	0.477 (7)	0.089 (8)	0.22
H15A	0.7620	0.7795	0.5565	0.107*	0.22
H15B	0.7010	0.8400	0.4735	0.107*	0.22
C16	0.772 (6)	0.681 (6)	0.384 (5)	0.124 (10)	0.22
H16A	0.8528	0.7432	0.3967	0.148*	0.22
H16B	0.7955	0.6044	0.3948	0.148*	0.22
C17	0.686 (9)	0.632 (10)	0.258 (7)	0.127 (10)	0.22
H17A	0.6103	0.6701	0.2635	0.191*	0.22
H17B	0.6587	0.5331	0.2181	0.191*	0.22
H17C	0.7333	0.6591	0.2105	0.191*	0.22
C14B	0.587 (10)	0.664 (4)	0.511 (7)	0.065 (6)	0.51
H14C	0.6522	0.6240	0.5402	0.078*	0.51
H14D	0.5129	0.5900	0.4515	0.078*	0.51
C15B	0.644 (4)	0.733 (3)	0.446 (3)	0.089 (8)	0.51
H15C	0.7198	0.8063	0.5038	0.107*	0.51
H15D	0.5797	0.7743	0.4161	0.107*	0.51
C16B	0.684 (4)	0.634 (3)	0.340 (4)	0.124 (10)	0.51
H16C	0.7401	0.5852	0.3687	0.148*	0.51
H16D	0.6065	0.5662	0.2783	0.148*	0.51
C17B	0.755 (3)	0.699 (4)	0.280 (3)	0.127 (10)	0.51
H17D	0.6927	0.7125	0.2216	0.191*	0.51
H17E	0.8077	0.6408	0.2368	0.191*	0.51
H17F	0.8104	0.7862	0.3418	0.191*	0.51
C14C	0.600 (19)	0.687 (6)	0.512 (13)	0.065 (6)	0.27
H14E	0.6634	0.6401	0.5342	0.078*	0.27
H14F	0.5301	0.6190	0.4404	0.078*	0.27
C15C	0.663 (7)	0.794 (6)	0.486 (5)	0.089 (8)	0.27
H15E	0.7464	0.8457	0.5474	0.107*	0.27
H15F	0.6072	0.8569	0.4877	0.107*	0.27
C16C	0.685 (6)	0.724 (4)	0.360 (5)	0.124 (10)	0.27
H16E	0.6005	0.6957	0.3002	0.148*	0.27
H16F	0.7398	0.7924	0.3497	0.148*	0.27
C17C	0.744 (8)	0.603 (6)	0.324 (7)	0.127 (10)	0.27
H17G	0.6755	0.5202	0.2812	0.191*	0.27
H17H	0.7975	0.6054	0.3965	0.191*	0.27
H17I	0.7974	0.6042	0.2696	0.191*	0.27
C18	0.7688 (13)	0.2311 (16)	0.7029 (15)	0.131 (6)
H18A	0.7283	0.1506	0.7073	0.157*
H18B	0.7266	0.2221	0.6226	0.157*
Cl1	0.75445 (19)	0.9363 (2)	0.79244 (19)	0.0594 (6)
Cl2	0.2839 (2)	0.6520 (2)	0.5385 (2)	0.0644 (6)
Cl3	0.4604 (2)	0.9945 (2)	0.65829 (19)	0.0549 (5)
Cl4	0.7400 (7)	0.3745 (6)	0.8168 (7)	0.234 (4)
Cl5	0.9241 (6)	0.2338 (7)	0.7127 (7)	0.214 (3)
N1	0.1814 (7)	0.8103 (7)	0.7781 (6)	0.0557 (18)
H1	0.197 (8)	0.773 (8)	0.707 (4)	0.067*
Sn1	0.52253 (6)	0.79582 (6)	0.66440 (5)	0.0525 (3)

	U11	U22	U33	U12	U13	U23
C1	0.039 (5)	0.055 (5)	0.045 (4)	0.004 (4)	0.005 (4)	0.020 (4)
C2	0.043 (5)	0.055 (5)	0.047 (4)	0.010 (4)	0.004 (4)	0.017 (4)
C3	0.069 (6)	0.091 (7)	0.047 (5)	0.012 (5)	0.016 (4)	0.035 (5)
C4	0.096 (8)	0.100 (8)	0.074 (6)	0.043 (7)	0.026 (6)	0.064 (6)
C5	0.081 (8)	0.090 (7)	0.090 (7)	0.035 (6)	0.004 (6)	0.063 (6)
C6	0.072 (7)	0.070 (6)	0.076 (6)	0.035 (5)	0.025 (5)	0.034 (5)
C7	0.044 (5)	0.058 (5)	0.043 (4)	0.011 (4)	0.010 (4)	0.009 (4)
C8	0.047 (5)	0.066 (5)	0.067 (5)	0.005 (4)	0.019 (4)	0.029 (5)
C9	0.075 (8)	0.103 (8)	0.086 (7)	−0.008 (6)	0.015 (6)	0.042 (7)
C10	0.052 (6)	0.086 (7)	0.078 (7)	−0.007 (5)	0.005 (5)	0.017 (6)
C11	0.045 (5)	0.077 (6)	0.080 (6)	0.020 (5)	0.017 (5)	0.037 (5)
C12	0.094 (9)	0.075 (7)	0.100 (8)	0.049 (6)	0.010 (7)	0.017 (6)
C13	0.110 (10)	0.158 (12)	0.091 (8)	0.076 (9)	0.029 (7)	0.075 (9)
C14	0.087 (17)	0.046 (13)	0.066 (7)	0.035 (16)	0.034 (9)	0.019 (12)
C15	0.09 (2)	0.09 (2)	0.062 (19)	0.00 (2)	0.042 (19)	0.004 (15)
C16	0.15 (3)	0.081 (18)	0.16 (2)	0.004 (19)	0.10 (2)	0.06 (2)
C17	0.16 (3)	0.14 (3)	0.095 (16)	0.04 (2)	0.038 (18)	0.060 (18)
C14B	0.087 (17)	0.046 (13)	0.066 (7)	0.035 (16)	0.034 (9)	0.019 (12)
C15B	0.09 (2)	0.09 (2)	0.062 (19)	0.00 (2)	0.042 (19)	0.004 (15)
C16B	0.15 (3)	0.081 (18)	0.16 (2)	0.004 (19)	0.10 (2)	0.06 (2)
C17B	0.16 (3)	0.14 (3)	0.095 (16)	0.04 (2)	0.038 (18)	0.060 (18)
C14C	0.087 (17)	0.046 (13)	0.066 (7)	0.035 (16)	0.034 (9)	0.019 (12)
C15C	0.09 (2)	0.09 (2)	0.062 (19)	0.00 (2)	0.042 (19)	0.004 (15)
C16C	0.15 (3)	0.081 (18)	0.16 (2)	0.004 (19)	0.10 (2)	0.06 (2)
C17C	0.16 (3)	0.14 (3)	0.095 (16)	0.04 (2)	0.038 (18)	0.060 (18)
C18	0.094 (10)	0.156 (13)	0.208 (16)	0.038 (9)	0.044 (10)	0.139 (13)
Cl1	0.0326 (11)	0.0740 (13)	0.0603 (12)	0.0032 (10)	0.0069 (9)	0.0261 (11)
Cl2	0.0525 (14)	0.0652 (13)	0.0581 (12)	0.0074 (11)	0.0045 (10)	0.0194 (11)
Cl3	0.0529 (13)	0.0512 (11)	0.0716 (13)	0.0172 (10)	0.0157 (10)	0.0374 (10)
Cl4	0.316 (10)	0.177 (5)	0.300 (8)	0.125 (6)	0.220 (8)	0.120 (5)
Cl5	0.163 (5)	0.303 (7)	0.364 (8)	0.147 (5)	0.150 (5)	0.264 (7)
N1	0.045 (4)	0.066 (4)	0.052 (4)	0.016 (4)	0.016 (3)	0.022 (4)
Sn1	0.0492 (4)	0.0576 (4)	0.0541 (4)	0.0190 (3)	0.0164 (3)	0.0262 (3)

C1—C6	1.385 (12)	C15—H15B	0.9700
C1—C2	1.396 (11)	C16—C17	1.48 (2)
C1—Sn1	2.137 (8)	C16—H16A	0.9700
C2—C3	1.421 (11)	C16—H16B	0.9700
C2—C7	1.506 (12)	C17—H17A	0.9600
C3—C4	1.376 (13)	C17—H17B	0.9600
C3—H3	0.9300	C17—H17C	0.9600
C4—C5	1.380 (14)	C14B—C15B	1.483 (18)
C4—H4	0.9300	C14B—Sn1	2.137 (12)
C5—C6	1.380 (13)	C14B—H14C	0.9700
C5—H5	0.9300	C14B—H14D	0.9700
C6—H6	0.9300	C15B—C16B	1.490 (18)
C7—N1	1.524 (11)	C15B—H15C	0.9700
C7—H7A	0.9700	C15B—H15D	0.9700
C7—H7B	0.9700	C16B—C17B	1.479 (18)
C8—N1	1.509 (11)	C16B—H16C	0.9700
C8—C10	1.529 (12)	C16B—H16D	0.9700
C8—C9	1.537 (14)	C17B—H17D	0.9600
C8—H8	0.9800	C17B—H17E	0.9600
C9—H9A	0.9600	C17B—H17F	0.9600
C9—H9B	0.9600	C14C—C15C	1.48 (2)
C9—H9C	0.9600	C14C—Sn1	2.139 (16)
C10—H10A	0.9600	C14C—H14E	0.9700
C10—H10B	0.9600	C14C—H14F	0.9700
C10—H10C	0.9600	C15C—C16C	1.49 (2)
C11—C13	1.500 (13)	C15C—H15E	0.9700
C11—C12	1.527 (13)	C15C—H15F	0.9700
C11—N1	1.535 (11)	C16C—C17C	1.48 (2)
C11—H11	0.9800	C16C—H16E	0.9700
C12—H12A	0.9600	C16C—H16F	0.9700
C12—H12B	0.9600	C17C—H17G	0.9600
C12—H12C	0.9600	C17C—H17H	0.9600
C13—H13A	0.9600	C17C—H17I	0.9600
C13—H13B	0.9600	C18—Cl5	1.632 (14)
C13—H13C	0.9600	C18—Cl4	1.721 (16)
C14—C15	1.481 (19)	C18—H18A	0.9700
C14—Sn1	2.141 (18)	C18—H18B	0.9700
C14—H14A	0.9700	Cl1—Sn1	2.547 (3)
C14—H14B	0.9700	Cl2—Sn1	2.608 (3)
C15—C16	1.485 (19)	Cl3—Sn1	2.406 (3)
C15—H15A	0.9700	N1—H1	0.857 (10)
C6—C1—C2	119.4 (8)	H17B—C17—H17C	109.5
C6—C1—Sn1	113.1 (6)	C15B—C14B—Sn1	114.6 (19)
C2—C1—Sn1	127.5 (6)	C15B—C14B—H14C	108.6
C1—C2—C3	118.7 (8)	Sn1—C14B—H14C	108.6
C1—C2—C7	125.5 (8)	C15B—C14B—H14D	108.6
C3—C2—C7	115.7 (8)	Sn1—C14B—H14D	108.6
C4—C3—C2	119.8 (9)	H14C—C14B—H14D	107.6
C4—C3—H3	120.1	C14B—C15B—C16B	111 (2)
C2—C3—H3	120.1	C14B—C15B—H15C	109.5
C3—C4—C5	121.5 (9)	C16B—C15B—H15C	109.5
C3—C4—H4	119.3	C14B—C15B—H15D	109.5
C5—C4—H4	119.3	C16B—C15B—H15D	109.5
C6—C5—C4	118.5 (9)	H15C—C15B—H15D	108.1
C6—C5—H5	120.7	C17B—C16B—C15B	113 (3)
C4—C5—H5	120.7	C17B—C16B—H16C	108.9
C5—C6—C1	122.1 (9)	C15B—C16B—H16C	108.9
C5—C6—H6	119.0	C17B—C16B—H16D	108.9
C1—C6—H6	119.0	C15B—C16B—H16D	108.9
C2—C7—N1	114.1 (7)	H16C—C16B—H16D	107.7
C2—C7—H7A	108.7	C16B—C17B—H17D	109.5
N1—C7—H7A	108.7	C16B—C17B—H17E	109.5
C2—C7—H7B	108.7	H17D—C17B—H17E	109.5
N1—C7—H7B	108.7	C16B—C17B—H17F	109.5
H7A—C7—H7B	107.6	H17D—C17B—H17F	109.5
N1—C8—C10	110.1 (7)	H17E—C17B—H17F	109.5
N1—C8—C9	110.6 (8)	C15C—C14C—Sn1	105 (3)
C10—C8—C9	111.8 (8)	C15C—C14C—H14E	110.8
N1—C8—H8	108.1	Sn1—C14C—H14E	110.8
C10—C8—H8	108.1	C15C—C14C—H14F	110.9
C9—C8—H8	108.1	Sn1—C14C—H14F	110.9
C8—C9—H9A	109.5	H14E—C14C—H14F	108.9
C8—C9—H9B	109.5	C14C—C15C—C16C	108 (4)
H9A—C9—H9B	109.5	C14C—C15C—H15E	110.2
C8—C9—H9C	109.5	C16C—C15C—H15E	110.2
H9A—C9—H9C	109.5	C14C—C15C—H15F	110.1
H9B—C9—H9C	109.5	C16C—C15C—H15F	110.1
C8—C10—H10A	109.5	H15E—C15C—H15F	108.5
C8—C10—H10B	109.5	C17C—C16C—C15C	121 (5)
H10A—C10—H10B	109.5	C17C—C16C—H16E	107.0
C8—C10—H10C	109.5	C15C—C16C—H16E	107.0
H10A—C10—H10C	109.5	C17C—C16C—H16F	107.0
H10B—C10—H10C	109.5	C15C—C16C—H16F	107.0
C13—C11—C12	111.4 (10)	H16E—C16C—H16F	106.8
C13—C11—N1	110.8 (8)	C16C—C17C—H17G	109.5
C12—C11—N1	112.6 (7)	C16C—C17C—H17H	109.5
C13—C11—H11	107.2	H17G—C17C—H17H	109.5
C12—C11—H11	107.2	C16C—C17C—H17I	109.5
N1—C11—H11	107.2	H17G—C17C—H17I	109.5
C11—C12—H12A	109.5	H17H—C17C—H17I	109.5
C11—C12—H12B	109.5	Cl5—C18—Cl4	114.1 (10)
H12A—C12—H12B	109.5	Cl5—C18—H18A	108.7
C11—C12—H12C	109.5	Cl4—C18—H18A	108.7
H12A—C12—H12C	109.5	Cl5—C18—H18B	108.7
H12B—C12—H12C	109.5	Cl4—C18—H18B	108.7
C11—C13—H13A	109.5	H18A—C18—H18B	107.6
C11—C13—H13B	109.5	C8—N1—C7	114.9 (7)
H13A—C13—H13B	109.5	C8—N1—C11	114.1 (7)
C11—C13—H13C	109.5	C7—N1—C11	113.3 (7)
H13A—C13—H13C	109.5	C8—N1—H1	108 (6)
H13B—C13—H13C	109.5	C7—N1—H1	105 (6)
C15—C14—Sn1	123 (4)	C11—N1—H1	100 (6)
C15—C14—H14A	106.6	C14B—Sn1—C1	126.9 (17)
Sn1—C14—H14A	106.6	C14B—Sn1—C14C	7(3)
C15—C14—H14B	106.6	C1—Sn1—C14C	132 (3)
Sn1—C14—H14B	106.6	C14B—Sn1—C14	19 (2)
H14A—C14—H14B	106.5	C1—Sn1—C14	145.8 (14)
C14—C15—C16	132 (5)	C14C—Sn1—C14	15 (5)
C14—C15—H15A	104.4	C14B—Sn1—Cl3	116.5 (18)
C16—C15—H15A	104.4	C1—Sn1—Cl3	116.5 (2)
C14—C15—H15B	104.4	C14C—Sn1—Cl3	111 (3)
C16—C15—H15B	104.4	C14—Sn1—Cl3	97.4 (13)
H15A—C15—H15B	105.6	C14B—Sn1—Cl1	93 (3)
C17—C16—C15	109 (7)	C1—Sn1—Cl1	89.0 (2)
C17—C16—H16A	109.9	C14C—Sn1—Cl1	89 (5)
C15—C16—H16A	109.9	C14—Sn1—Cl1	95.1 (16)
C15—C16—H16B	109.9	Cl3—Sn1—Cl1	90.96 (9)
H16A—C16—H16B	108.3	C14B—Sn1—Cl2	88 (3)
C16—C17—H17A	109.5	C1—Sn1—Cl2	89.5 (2)
C16—C17—H17B	109.5	C14C—Sn1—Cl2	92 (5)
H17A—C17—H17B	109.5	C14—Sn1—Cl2	86.3 (16)
C16—C17—H17C	109.5	Cl3—Sn1—Cl2	89.46 (9)
H17A—C17—H17C	109.5	Cl1—Sn1—Cl2	178.50 (7)
C6—C1—C2—C3	2.3 (12)	C15B—C14B—Sn1—C1	−158 (5)
Sn1—C1—C2—C3	−176.8 (6)	C15B—C14B—Sn1—C14	29 (6)
C6—C1—C2—C7	177.9 (8)	C15B—C14B—Sn1—Cl3	26 (8)
Sn1—C1—C2—C7	−1.2 (12)	C15B—C14B—Sn1—Cl1	−67 (7)
C1—C2—C3—C4	−2.4 (13)	C15B—C14B—Sn1—Cl2	114 (7)
C7—C2—C3—C4	−178.4 (9)	C6—C1—Sn1—C14B	30 (4)
C2—C3—C4—C5	1.8 (16)	C2—C1—Sn1—C14B	−151 (4)
C3—C4—C5—C6	−1.0 (17)	C6—C1—Sn1—C14C	24 (7)
C4—C5—C6—C1	0.9 (16)	C2—C1—Sn1—C14C	−157 (7)
C2—C1—C6—C5	−1.5 (14)	C6—C1—Sn1—C14	34 (3)
Sn1—C1—C6—C5	177.7 (8)	C2—C1—Sn1—C14	−147 (3)
C1—C2—C7—N1	88.7 (10)	C6—C1—Sn1—Cl3	−154.2 (6)
C3—C2—C7—N1	−95.6 (8)	C2—C1—Sn1—Cl3	25.0 (8)
Sn1—C14—C15—C16	154 (8)	C6—C1—Sn1—Cl1	−63.6 (6)
C14—C15—C16—C17	52 (13)	C2—C1—Sn1—Cl1	115.5 (7)
Sn1—C14B—C15B—C16B	−179 (5)	C6—C1—Sn1—Cl2	116.6 (6)
C14B—C15B—C16B—C17B	−174 (6)	C2—C1—Sn1—Cl2	−64.2 (7)
Sn1—C14C—C15C—C16C	−164 (7)	C15C—C14C—Sn1—C1	−147 (7)
C14C—C15C—C16C—C17C	−47 (12)	C15C—C14C—Sn1—C14	54 (9)
C10—C8—N1—C7	−160.6 (7)	C15C—C14C—Sn1—Cl3	31 (13)
C9—C8—N1—C7	75.3 (9)	C15C—C14C—Sn1—Cl1	−60 (11)
C10—C8—N1—C11	66.2 (9)	C15C—C14C—Sn1—Cl2	121 (11)
C9—C8—N1—C11	−57.9 (10)	C15—C14—Sn1—C14B	−91 (12)
C2—C7—N1—C8	49.8 (9)	C15—C14—Sn1—C1	−101 (6)
C2—C7—N1—C11	−176.6 (7)	C15—C14—Sn1—C14C	−72 (18)
C13—C11—N1—C8	−126.3 (9)	C15—C14—Sn1—Cl3	86 (6)
C12—C11—N1—C8	108.2 (9)	C15—C14—Sn1—Cl1	−5(6)
C13—C11—N1—C7	99.7 (9)	C15—C14—Sn1—Cl2	175 (6)
C12—C11—N1—C7	−25.8 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Cl2	0.86 (1)	2.37 (7)	3.208 (8)	165 (8)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Cl2	0.86 (1)	2.37 (7)	3.208 (8)	165 (8)