Literature DB >> 21580269

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

James L Wardell, Solange M S V Wardell, Edward R T Tiekink, Geraldo M de Lima.

Abstract

In the title salt, (C(17)H(17)F(6)n class="Chemical">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.

Entities: CellLine Chemical Disease Gene Species

Year: 2010 PMID： 21580269 PMCID： PMC2983573 DOI： 10.1107/S1600536810006574

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

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 ▶); n class="Chemical">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[n class="Chemical">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
M_r = 1173.34	F(000) = 590
Triclinic, P1	D_x = 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	R_int = 0.094
Detector resolution: 9.091 pixels mm^-1	θ_max = 25.0°, θ_min = 3.0°
φ and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2007)	k = −10→10
T_min = 0.843, T_max = 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(F_o²) + (0.1P)² + 9.2689P] where P = (F_o² + 2F_c²)/3
4164 reflections	(Δ/σ)_max = 0.001
314 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −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	U_iso*/U_eq
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···Cl2^iv	0.84	2.21	3.028 (6)	167
C20—H20···Cl2^v	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⋯Cl2^iv	0.95	2.76	3.557 (9)	142

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

9 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Conformation stability and organization of mefloquine molecules in different environments.

Authors: Agnieszka Skórska; Jan Sliwiński; Barbara J Oleksyn
Journal: Bioorg Med Chem Lett Date: 2005-11-21 Impact factor: 2.823

3. Mefloquine is highly efficacious against chloroquine-resistant Plasmodium vivax malaria and Plasmodium falciparum malaria in Papua, Indonesia.

Authors: Jason D Maguire; Hariyani Marwoto; Thomas L Richie; David J Fryauff; J Kevin Baird
Journal: Clin Infect Dis Date: 2006-03-13 Impact factor: 9.079

4. Synthesis and biological evaluation of new imidazo[1,2-a]pyridine derivatives designed as mefloquine analogues.

Authors: Patricia C Lima; Mitchell A Avery; Babu L Tekwani; Helio M de Alves; Eliezer J Barreiro; Carlos A M Fraga
Journal: Farmaco Date: 2002-10

5. Crystal structure of (-)-mefloquine hydrochloride reveals consistency of configuration with biological activity.

Authors: Jean M Karle; Isabella L Karle
Journal: Antimicrob Agents Chemother Date: 2002-05 Impact factor: 5.191

6. Synthetic ferrocenic mefloquine and quinine analoguesas potential antimalarial agents.

Authors: C Biot; L Delhaes; L A Maciejewski; M Mortuaire; D Camus; D Dive; J S Brocard
Journal: Eur J Med Chem Date: 2000 Jul-Aug Impact factor: 6.514

7. Crystal structure and molecular structure of mefloquine methylsulfonate monohydrate: implications for a malaria receptor.

Authors: J M Karle; I L Karle
Journal: Antimicrob Agents Chemother Date: 1991-11 Impact factor: 5.191

8. The antimalarial potential of 4-quinolinecarbinolamines may be limited due to neurotoxicity and cross-resistance in mefloquine-resistant Plasmodium falciparum strains.

Authors: Geoffrey S Dow; Michael L Koenig; Lesley Wolf; Lucia Gerena; Miriam Lopez-Sanchez; Thomas H Hudson; Apurba K Bhattacharjee
Journal: Antimicrob Agents Chemother Date: 2004-07 Impact factor: 5.191

9. Adverse effects of the antimalaria drug, mefloquine: due to primary liver damage with secondary thyroid involvement?

Authors: Ashley M Croft; Andrew Herxheimer
Journal: BMC Public Health Date: 2002-03-25 Impact factor: 3.295