Bis(2-{[2,8-bis-(trifluoro-meth-yl)quinolin-4-yl](hydr-oxy)meth-yl}piperidin-1-ium) tetra-chloridodiphenyl-stannate(IV).

In the title salt, (C(17)H(17)F(6)N(2)O)(2)[Sn(C(6)H(5))(2)Cl(4)], the complete anion is generated by crystallograaphic inversion symmetry, giving a trans-SnC(2)Cl(4) octa-hedral coordination geometry for the metal atom. In the cation, the quinoline residue is almost normal to the other atoms, so that the ion has an L-shaped conformation [the C-C-C-C torsion angle linking the fused-ring systems is 100.9 (7)°]; the six-membered piperidin-1-ium ring has a chair conformation. An intra-molecular N-H⋯O inter-action occurs. In the crystal, N-H⋯Cl and O-H⋯Cl hydrogen bonds link the components into a supra-molecular chain propagating along the a axis. C-H⋯Cl inter-actions are also present.

Related literature

For information on mefloquine and its derivatives, see: Kunin & Ellis (2007 ▶); Maguire et al. (2006 ▶); Dow et al. (2004 ▶); Croft & Herxheimer (2002 ▶); Lima et al. (2002 ▶); Biot et al. (2000 ▶); Roesner et al. (1981 ▶). For the crystal structures of mefloquine and its salts, see: Obaleye et al. (2009 ▶); Skórska et al. (2005 ▶); Karle & Karle (1991a ▶,b ▶, 2002 ▶).

Experimental

Crystal data

(C17H17F6N2O)2[Sn(C6H5)2Cl4]

M = 1173.34

Triclinic,

a = 8.5578 (4) Å

b = 9.1479 (7) Å

c = 15.9866 (11) Å

α = 104.739 (3)°

β = 91.671 (4)°

γ = 97.622 (4)°

V = 1197.06 (14) Å3

Z = 1

Mo Kα radiation

μ = 0.85 mm−1

T = 120 K

0.08 × 0.04 × 0.01 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2007 ▶) T min = 0.843, T max = 1.000

16610 measured reflections

4164 independent reflections

3313 reflections with I > 2σ(I)

R int = 0.094

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.198

S = 1.03

4164 reflections

314 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.61 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810006574/hb5338sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810006574/hb5338Isup2.hkl

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

(C17H17F6N2O)2[Sn(C6H5)2Cl4]	Z = 1
Mr = 1173.34	F(000) = 590
Triclinic, P1	Dx = 1.628 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5578 (4) Å	Cell parameters from 37314 reflections
b = 9.1479 (7) Å	θ = 2.9–27.5°
c = 15.9866 (11) Å	µ = 0.85 mm−1
α = 104.739 (3)°	T = 120 K
β = 91.671 (4)°	Lath, colourless
γ = 97.622 (4)°	0.08 × 0.04 × 0.01 mm
V = 1197.06 (14) Å3

Nonius KappaCCD diffractometer	4164 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	3313 reflections with I > 2σ(I)
10 cm confocal mirrors	Rint = 0.094
Detector resolution: 9.091 pixels mm-1	θmax = 25.0°, θmin = 3.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −10→10
Tmin = 0.843, Tmax = 1.000	l = −19→19
16610 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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.198	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.1P)2 + 9.2689P] where P = (Fo2 + 2Fc2)/3
4164 reflections	(Δ/σ)max = 0.001
314 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.61 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
F1	1.4043 (6)	0.6359 (8)	0.5099 (4)	0.0544 (16)
F2	1.2203 (6)	0.5658 (6)	0.5835 (4)	0.0440 (14)
F3	1.3067 (6)	0.8005 (6)	0.6046 (3)	0.0444 (14)
F4	0.7444 (5)	0.7621 (5)	0.6107 (3)	0.0313 (11)
F5	0.8916 (5)	0.9772 (5)	0.6216 (3)	0.0352 (12)
F6	0.6421 (5)	0.9568 (6)	0.5959 (3)	0.0357 (12)
O1	1.2216 (6)	0.5258 (7)	0.2147 (4)	0.0298 (13)
H1O	1.2615	0.5781	0.1824	0.045*
N1	1.0279 (7)	0.7459 (7)	0.5071 (4)	0.0192 (13)
N2	0.9662 (8)	0.3538 (7)	0.1053 (4)	0.0253 (15)
H1N	0.9283	0.4242	0.0810	0.030*
H2N	1.0704	0.3526	0.0929	0.030*
C1	1.1479 (8)	0.6823 (9)	0.4755 (5)	0.0216 (16)
C2	1.1698 (9)	0.6207 (9)	0.3865 (5)	0.0229 (17)
H2	1.2600	0.5738	0.3684	0.027*
C3	1.0535 (8)	0.6320 (8)	0.3274 (5)	0.0203 (16)
C4	0.9256 (8)	0.7103 (8)	0.3568 (5)	0.0175 (15)
C5	0.8083 (8)	0.7384 (8)	0.3013 (5)	0.0184 (15)
H5	0.8148	0.7064	0.2403	0.022*
C6	0.6856 (9)	0.8109 (9)	0.3343 (5)	0.0243 (17)
H6	0.6084	0.8298	0.2960	0.029*
C7	0.6721 (9)	0.8581 (9)	0.4245 (5)	0.0257 (17)
H7	0.5838	0.9052	0.4461	0.031*
C8	0.7842 (9)	0.8372 (8)	0.4816 (5)	0.0221 (16)
C9	0.9155 (8)	0.7627 (8)	0.4485 (5)	0.0191 (15)
C10	1.2703 (9)	0.6709 (9)	0.5419 (5)	0.0259 (17)
C11	0.7672 (9)	0.8840 (9)	0.5768 (5)	0.0261 (18)
C12	1.0672 (8)	0.5601 (8)	0.2328 (5)	0.0222 (17)
H12	1.0380	0.6303	0.1981	0.027*
C13	0.9577 (9)	0.4048 (9)	0.2023 (5)	0.0231 (17)
H13	0.8468	0.4208	0.2157	0.028*
C14	0.8746 (10)	0.1981 (10)	0.0636 (6)	0.0317 (19)
H14A	0.8919	0.1690	0.0009	0.038*
H14B	0.7603	0.2011	0.0700	0.038*
C15	0.9281 (10)	0.0804 (10)	0.1060 (6)	0.0308 (19)
H15A	0.8642	−0.0204	0.0801	0.037*
H15B	1.0401	0.0713	0.0951	0.037*
C16	0.9102 (10)	0.1257 (10)	0.2019 (6)	0.0317 (19)
H16A	0.9485	0.0493	0.2285	0.038*
H16B	0.7971	0.1274	0.2129	0.038*
C17	1.0039 (9)	0.2834 (9)	0.2434 (5)	0.0241 (17)
H17A	0.9859	0.3127	0.3060	0.029*
H17B	1.1180	0.2781	0.2377	0.029*
Sn	0.5000	0.5000	1.0000	0.0191 (3)
Cl1	0.2014 (2)	0.3929 (2)	0.94923 (12)	0.0246 (4)
Cl2	0.5841 (2)	0.2788 (2)	0.88282 (13)	0.0306 (5)
C18	0.5166 (8)	0.6443 (8)	0.9137 (5)	0.0193 (16)
C19	0.5741 (9)	0.7987 (8)	0.9438 (5)	0.0228 (17)
H19	0.6049	0.8408	1.0036	0.027*
C20	0.5871 (9)	0.8925 (9)	0.8875 (6)	0.0291 (19)
H20	0.6235	0.9987	0.9091	0.035*
C21	0.5471 (10)	0.8308 (10)	0.7998 (6)	0.0308 (19)
H21	0.5603	0.8944	0.7611	0.037*
C22	0.4875 (9)	0.6764 (9)	0.7677 (5)	0.0271 (18)
H22	0.4569	0.6345	0.7078	0.033*
C23	0.4740 (8)	0.5857 (9)	0.8251 (5)	0.0234 (17)
H23	0.4346	0.4801	0.8037	0.028*

	U11	U22	U33	U12	U13	U23
F1	0.027 (3)	0.093 (5)	0.047 (3)	0.027 (3)	−0.001 (2)	0.016 (3)
F2	0.042 (3)	0.039 (3)	0.054 (3)	−0.006 (2)	−0.018 (3)	0.028 (3)
F3	0.050 (3)	0.035 (3)	0.043 (3)	0.001 (2)	−0.025 (2)	0.006 (2)
F4	0.033 (3)	0.032 (3)	0.030 (3)	0.009 (2)	0.005 (2)	0.008 (2)
F5	0.032 (3)	0.031 (3)	0.035 (3)	0.001 (2)	−0.001 (2)	−0.004 (2)
F6	0.032 (3)	0.042 (3)	0.034 (3)	0.022 (2)	0.008 (2)	0.002 (2)
O1	0.026 (3)	0.038 (3)	0.034 (3)	0.013 (3)	0.015 (2)	0.018 (3)
N1	0.017 (3)	0.013 (3)	0.024 (3)	−0.001 (2)	0.002 (3)	0.002 (3)
N2	0.030 (4)	0.026 (4)	0.023 (4)	0.011 (3)	0.007 (3)	0.008 (3)
C1	0.017 (4)	0.023 (4)	0.027 (4)	0.001 (3)	0.007 (3)	0.009 (3)
C2	0.020 (4)	0.019 (4)	0.028 (4)	0.004 (3)	−0.002 (3)	0.004 (3)
C3	0.021 (4)	0.012 (4)	0.026 (4)	−0.005 (3)	0.005 (3)	0.004 (3)
C4	0.021 (4)	0.011 (3)	0.022 (4)	0.000 (3)	0.006 (3)	0.006 (3)
C5	0.022 (4)	0.013 (4)	0.020 (4)	0.000 (3)	−0.001 (3)	0.004 (3)
C6	0.031 (4)	0.023 (4)	0.023 (4)	0.007 (3)	0.000 (3)	0.010 (3)
C7	0.027 (4)	0.019 (4)	0.034 (5)	0.011 (3)	0.003 (3)	0.009 (3)
C8	0.028 (4)	0.010 (4)	0.026 (4)	0.002 (3)	0.002 (3)	−0.001 (3)
C9	0.019 (4)	0.013 (4)	0.024 (4)	0.001 (3)	−0.003 (3)	0.004 (3)
C10	0.024 (4)	0.027 (4)	0.027 (4)	0.005 (3)	0.001 (3)	0.005 (4)
C11	0.028 (4)	0.022 (4)	0.029 (4)	0.001 (3)	−0.001 (3)	0.011 (3)
C12	0.018 (4)	0.019 (4)	0.031 (4)	0.015 (3)	0.007 (3)	0.002 (3)
C13	0.024 (4)	0.024 (4)	0.021 (4)	0.007 (3)	0.013 (3)	0.002 (3)
C14	0.031 (4)	0.029 (5)	0.028 (5)	0.007 (4)	−0.001 (4)	−0.006 (4)
C15	0.026 (4)	0.027 (5)	0.036 (5)	0.000 (3)	−0.006 (4)	0.004 (4)
C16	0.031 (4)	0.033 (5)	0.039 (5)	0.015 (4)	0.004 (4)	0.017 (4)
C17	0.022 (4)	0.026 (4)	0.023 (4)	0.001 (3)	−0.001 (3)	0.006 (3)
Sn	0.0219 (4)	0.0159 (4)	0.0223 (4)	0.0064 (3)	0.0051 (3)	0.0081 (3)
Cl1	0.0218 (9)	0.0258 (10)	0.0282 (10)	0.0037 (7)	0.0014 (8)	0.0104 (8)
Cl2	0.0438 (12)	0.0208 (10)	0.0316 (11)	0.0129 (9)	0.0151 (9)	0.0090 (9)
C18	0.011 (3)	0.022 (4)	0.029 (4)	0.007 (3)	0.007 (3)	0.012 (3)
C19	0.027 (4)	0.016 (4)	0.029 (4)	0.009 (3)	0.007 (3)	0.008 (3)
C20	0.023 (4)	0.021 (4)	0.048 (6)	0.005 (3)	0.013 (4)	0.016 (4)
C21	0.033 (5)	0.040 (5)	0.030 (5)	0.019 (4)	0.007 (4)	0.022 (4)
C22	0.024 (4)	0.031 (5)	0.026 (4)	0.008 (3)	0.004 (3)	0.006 (4)
C23	0.019 (4)	0.025 (4)	0.029 (4)	0.010 (3)	0.007 (3)	0.007 (3)

F1—C10	1.314 (9)	C12—H12	1.0000
F2—C10	1.334 (10)	C13—C17	1.515 (11)
F3—C10	1.336 (9)	C13—H13	1.0000
F4—C11	1.353 (9)	C14—C15	1.521 (12)
F5—C11	1.333 (9)	C14—H14A	0.9900
F6—C11	1.337 (9)	C14—H14B	0.9900
O1—C12	1.419 (8)	C15—C16	1.501 (12)
O1—H1O	0.8400	C15—H15A	0.9900
N1—C1	1.299 (9)	C15—H15B	0.9900
N1—C9	1.373 (10)	C16—C17	1.529 (11)
N2—C14	1.509 (10)	C16—H16A	0.9900
N2—C13	1.509 (10)	C16—H16B	0.9900
N2—H1N	0.9200	C17—H17A	0.9900
N2—H2N	0.9200	C17—H17B	0.9900
C1—C2	1.418 (11)	Sn—C18i	2.135 (7)
C1—C10	1.502 (11)	Sn—C18	2.135 (7)
C2—C3	1.385 (11)	Sn—Cl2i	2.5804 (19)
C2—H2	0.9500	Sn—Cl2	2.5804 (19)
C3—C4	1.414 (10)	Sn—Cl1i	2.6382 (18)
C3—C12	1.503 (10)	Sn—Cl1	2.6382 (18)
C4—C5	1.411 (10)	C18—C19	1.387 (11)
C4—C9	1.431 (10)	C18—C23	1.399 (11)
C5—C6	1.363 (11)	C19—C20	1.390 (11)
C5—H5	0.9500	C19—H19	0.9500
C6—C7	1.409 (11)	C20—C21	1.385 (12)
C6—H6	0.9500	C20—H20	0.9500
C7—C8	1.369 (11)	C21—C22	1.394 (12)
C7—H7	0.9500	C21—H21	0.9500
C8—C9	1.436 (10)	C22—C23	1.383 (11)
C8—C11	1.490 (11)	C22—H22	0.9500
C12—C13	1.549 (11)	C23—H23	0.9500
C12—O1—H1O	109.5	C12—C13—H13	109.0
C1—N1—C9	116.8 (6)	N2—C14—C15	110.0 (7)
C14—N2—C13	114.1 (6)	N2—C14—H14A	109.7
C14—N2—H1N	108.7	C15—C14—H14A	109.7
C13—N2—H1N	108.7	N2—C14—H14B	109.7
C14—N2—H2N	108.7	C15—C14—H14B	109.7
C13—N2—H2N	108.7	H14A—C14—H14B	108.2
H1N—N2—H2N	107.6	C16—C15—C14	110.8 (7)
N1—C1—C2	126.4 (7)	C16—C15—H15A	109.5
N1—C1—C10	114.9 (7)	C14—C15—H15A	109.5
C2—C1—C10	118.7 (6)	C16—C15—H15B	109.5
C3—C2—C1	116.9 (7)	C14—C15—H15B	109.5
C3—C2—H2	121.5	H15A—C15—H15B	108.1
C1—C2—H2	121.5	C15—C16—C17	110.7 (7)
C2—C3—C4	119.8 (7)	C15—C16—H16A	109.5
C2—C3—C12	118.7 (7)	C17—C16—H16A	109.5
C4—C3—C12	121.6 (7)	C15—C16—H16B	109.5
C5—C4—C3	124.0 (7)	C17—C16—H16B	109.5
C5—C4—C9	118.7 (6)	H16A—C16—H16B	108.1
C3—C4—C9	117.3 (7)	C13—C17—C16	112.4 (6)
C6—C5—C4	120.8 (7)	C13—C17—H17A	109.1
C6—C5—H5	119.6	C16—C17—H17A	109.1
C4—C5—H5	119.6	C13—C17—H17B	109.1
C5—C6—C7	120.8 (7)	C16—C17—H17B	109.1
C5—C6—H6	119.6	H17A—C17—H17B	107.9
C7—C6—H6	119.6	C18i—Sn—C18	180.0
C8—C7—C6	121.1 (7)	C18i—Sn—Cl2i	91.2 (2)
C8—C7—H7	119.4	C18—Sn—Cl2i	88.8 (2)
C6—C7—H7	119.4	C18i—Sn—Cl2	88.8 (2)
C7—C8—C9	119.2 (7)	C18—Sn—Cl2	91.2 (2)
C7—C8—C11	120.8 (7)	Cl2i—Sn—Cl2	180.0
C9—C8—C11	120.0 (7)	C18i—Sn—Cl1i	92.46 (19)
N1—C9—C4	122.6 (6)	C18—Sn—Cl1i	87.54 (19)
N1—C9—C8	118.0 (7)	Cl2i—Sn—Cl1i	89.46 (6)
C4—C9—C8	119.4 (6)	Cl2—Sn—Cl1i	90.54 (6)
F1—C10—F2	106.4 (7)	C18i—Sn—Cl1	87.54 (19)
F1—C10—F3	106.4 (7)	C18—Sn—Cl1	92.46 (19)
F2—C10—F3	104.6 (7)	Cl2i—Sn—Cl1	90.54 (6)
F1—C10—C1	114.0 (7)	Cl2—Sn—Cl1	89.46 (6)
F2—C10—C1	112.1 (6)	Cl1i—Sn—Cl1	180.0
F3—C10—C1	112.6 (6)	C19—C18—C23	118.1 (7)
F5—C11—F6	106.3 (6)	C19—C18—Sn	120.6 (6)
F5—C11—F4	106.7 (6)	C23—C18—Sn	121.2 (6)
F6—C11—F4	105.9 (6)	C18—C19—C20	120.8 (8)
F5—C11—C8	113.8 (6)	C18—C19—H19	119.6
F6—C11—C8	111.7 (6)	C20—C19—H19	119.6
F4—C11—C8	111.8 (6)	C21—C20—C19	119.9 (8)
O1—C12—C3	112.3 (6)	C21—C20—H20	120.1
O1—C12—C13	105.2 (6)	C19—C20—H20	120.1
C3—C12—C13	111.0 (6)	C20—C21—C22	120.7 (8)
O1—C12—H12	109.4	C20—C21—H21	119.6
C3—C12—H12	109.4	C22—C21—H21	119.6
C13—C12—H12	109.4	C23—C22—C21	118.3 (8)
N2—C13—C17	110.0 (6)	C23—C22—H22	120.8
N2—C13—C12	106.0 (6)	C21—C22—H22	120.8
C17—C13—C12	113.8 (6)	C22—C23—C18	122.2 (7)
N2—C13—H13	109.0	C22—C23—H23	118.9
C17—C13—H13	109.0	C18—C23—H23	118.9
C9—N1—C1—C2	−3.9 (11)	C9—C8—C11—F6	177.6 (6)
C9—N1—C1—C10	178.1 (6)	C7—C8—C11—F4	113.1 (8)
N1—C1—C2—C3	1.4 (11)	C9—C8—C11—F4	−63.9 (9)
C10—C1—C2—C3	179.3 (7)	C2—C3—C12—O1	−16.4 (9)
C1—C2—C3—C4	3.6 (10)	C4—C3—C12—O1	163.5 (6)
C1—C2—C3—C12	−176.4 (6)	C2—C3—C12—C13	100.9 (7)
C2—C3—C4—C5	174.8 (7)	C4—C3—C12—C13	−79.1 (8)
C12—C3—C4—C5	−5.1 (11)	C14—N2—C13—C17	52.8 (8)
C2—C3—C4—C9	−5.6 (10)	C14—N2—C13—C12	176.3 (6)
C12—C3—C4—C9	174.4 (6)	O1—C12—C13—N2	−65.2 (7)
C3—C4—C5—C6	178.1 (7)	C3—C12—C13—N2	173.1 (6)
C9—C4—C5—C6	−1.4 (10)	O1—C12—C13—C17	55.8 (8)
C4—C5—C6—C7	−0.7 (11)	C3—C12—C13—C17	−65.9 (8)
C5—C6—C7—C8	2.2 (12)	C13—N2—C14—C15	−55.2 (9)
C6—C7—C8—C9	−1.4 (11)	N2—C14—C15—C16	56.7 (9)
C6—C7—C8—C11	−178.5 (7)	C14—C15—C16—C17	−57.5 (9)
C1—N1—C9—C4	1.4 (10)	N2—C13—C17—C16	−52.3 (8)
C1—N1—C9—C8	−178.0 (6)	C12—C13—C17—C16	−171.1 (6)
C5—C4—C9—N1	−177.2 (7)	C15—C16—C17—C13	56.0 (9)
C3—C4—C9—N1	3.2 (10)	Cl2i—Sn—C18—C19	37.8 (5)
C5—C4—C9—C8	2.1 (10)	Cl2—Sn—C18—C19	−142.2 (5)
C3—C4—C9—C8	−177.4 (6)	Cl1i—Sn—C18—C19	−51.7 (5)
C7—C8—C9—N1	178.7 (7)	Cl1—Sn—C18—C19	128.3 (5)
C11—C8—C9—N1	−4.2 (10)	Cl2i—Sn—C18—C23	−143.9 (5)
C7—C8—C9—C4	−0.7 (10)	Cl2—Sn—C18—C23	36.1 (5)
C11—C8—C9—C4	176.4 (7)	Cl1i—Sn—C18—C23	126.6 (5)
N1—C1—C10—F1	−166.8 (7)	Cl1—Sn—C18—C23	−53.4 (5)
C2—C1—C10—F1	15.1 (10)	C23—C18—C19—C20	0.7 (10)
N1—C1—C10—F2	72.2 (9)	Sn—C18—C19—C20	179.1 (5)
C2—C1—C10—F2	−106.0 (8)	C18—C19—C20—C21	−2.0 (11)
N1—C1—C10—F3	−45.4 (9)	C19—C20—C21—C22	2.6 (12)
C2—C1—C10—F3	136.4 (7)	C20—C21—C22—C23	−1.9 (11)
C7—C8—C11—F5	−125.8 (8)	C21—C22—C23—C18	0.6 (11)
C9—C8—C11—F5	57.1 (9)	C19—C18—C23—C22	0.0 (10)
C7—C8—C11—F6	−5.4 (10)	Sn—C18—C23—C22	−178.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2n···O1	0.92	2.39	2.789 (9)	106
N2—H1n···Cl1ii	0.92	2.27	3.166 (7)	166
N2—H2n···Cl1iii	0.92	2.67	3.311 (7)	127
O1—H1o···Cl2iv	0.84	2.21	3.028 (6)	167
C20—H20···Cl2v	0.95	2.76	3.557 (9)	142

Table 1

Selected bond lengths (Å)

Sn—C18	2.135 (7)
Sn—Cl2	2.5804 (19)
Sn—Cl1	2.6382 (18)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2n⋯O1	0.92	2.39	2.789 (9)	106
N2—H1n⋯Cl1i	0.92	2.27	3.166 (7)	166
N2—H2n⋯Cl1ii	0.92	2.67	3.311 (7)	127
O1—H1o⋯Cl2iii	0.84	2.21	3.028 (6)	167
C20—H20⋯Cl2iv	0.95	2.76	3.557 (9)	142

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