8-Hy-droxy-2-methyl-quinolinium tetra-chlorido(quinolin-2-olato-κN,O)stannate(IV) methanol disolvate.

In the reaction of 8-hy-droxy-quinoline, 2-methyl-8-hy-droxy-quinoline and stannic chloride, the 2-methyl-8-hy-droxy-quinoline is protonated, yielding the disolvated title salt, (C(10)H(10)NO)[SnCl(4)(C(9)H(6)NO)]·2CH(3)OH. The Sn(IV) atom in the anion is N,O-chelated by the hy-droxy-quinolinate in a cis-SnNOCl(4) octa-hedral geometry. In the crystal, the cation, anion and solvent mol-ecules are linked by N-H⋯O, O-H⋯O and O-H⋯Cl hydrogen bonds, generating a three-dimensional network.

Related literature

For related tin–oxinate structures, see: Archer et al. (1987 ▶); Faza­eli et al. (2009 ▶); Lo & Ng (2009 ▶).

Experimental

Crystal data

(C10H10NO)[SnCl4(C9H6NO)]·2CH4O

M = 628.91

Triclinic,

a = 7.9395 (3) Å

b = 9.9721 (4) Å

c = 16.0531 (8) Å

α = 75.056 (4)°

β = 82.529 (4)°

γ = 88.529 (3)°

V = 1217.53 (9) Å3

Z = 2

Mo Kα radiation

μ = 1.52 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010 ▶) T min = 0.659, T max = 0.751

8825 measured reflections

5371 independent reflections

4258 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.130

S = 1.05

5371 reflections

295 parameters

H-atom parameters constrained

Δρmax = 1.76 e Å−3

Δρmin = −1.85 e Å−3

Data collection: CrysAlis PRO (Agilent Technologies, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811001954/si2328sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001954/si2328Isup2.hkl

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

(C10H10NO)[SnCl4(C9H6NO)]·2CH4O	Z = 2
Mr = 628.91	F(000) = 628
Triclinic, P1	Dx = 1.715 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.9395 (3) Å	Cell parameters from 4114 reflections
b = 9.9721 (4) Å	θ = 2.6–29.3°
c = 16.0531 (8) Å	µ = 1.52 mm−1
α = 75.056 (4)°	T = 100 K
β = 82.529 (4)°	Prism, yellow
γ = 88.529 (3)°	0.30 × 0.25 × 0.20 mm
V = 1217.53 (9) Å3

Agilent SuperNova Dual diffractometer with an Atlas detector	5371 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4258 reflections with I > 2σ(I)
Mirror	Rint = 0.040
Detector resolution: 10.4041 pixels mm-1	θmax = 27.5°, θmin = 2.6°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	k = −11→12
Tmin = 0.659, Tmax = 0.751	l = −16→20
8825 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0633P)2] where P = (Fo2 + 2Fc2)/3
5371 reflections	(Δ/σ)max = 0.001
295 parameters	Δρmax = 1.76 e Å−3
0 restraints	Δρmin = −1.85 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.51336 (4)	0.56573 (3)	0.20809 (2)	0.01909 (12)
Cl1	0.24880 (15)	0.54380 (11)	0.30721 (8)	0.0232 (3)
Cl2	0.47350 (15)	0.33873 (11)	0.18991 (8)	0.0242 (3)
Cl3	0.67740 (16)	0.50347 (12)	0.32577 (8)	0.0262 (3)
Cl4	0.75884 (15)	0.60727 (11)	0.09839 (8)	0.0227 (3)
O1	0.5234 (4)	0.7725 (3)	0.2102 (2)	0.0203 (7)
O2	0.8013 (5)	1.0336 (3)	0.3161 (2)	0.0280 (8)
H2	0.8017	0.9885	0.2786	0.042*
O3	0.8327 (4)	0.8959 (3)	0.1982 (2)	0.0253 (8)
H3	0.7453	0.8506	0.1976	0.038*
O4	1.0402 (4)	1.2688 (3)	0.3035 (2)	0.0262 (8)
H4	1.1279	1.3129	0.3052	0.039*
N1	0.3617 (5)	0.6649 (4)	0.1035 (2)	0.0191 (8)
N2	0.8391 (5)	1.1312 (4)	0.4535 (3)	0.0216 (9)
H2N	0.8831	1.1741	0.4004	0.032*
C1	0.2875 (6)	0.6087 (5)	0.0509 (3)	0.0235 (10)
H1	0.2968	0.5117	0.0565	0.028*
C2	0.1958 (6)	0.6896 (5)	−0.0127 (3)	0.0256 (11)
H2A	0.1428	0.6470	−0.0492	0.031*
C3	0.1824 (6)	0.8287 (5)	−0.0226 (3)	0.0215 (10)
H3A	0.1215	0.8834	−0.0663	0.026*
C4	0.2598 (6)	0.8921 (5)	0.0328 (3)	0.0211 (10)
C5	0.2544 (6)	1.0356 (5)	0.0277 (3)	0.0219 (10)
H5	0.1940	1.0964	−0.0139	0.026*
C6	0.3369 (6)	1.0866 (5)	0.0830 (3)	0.0247 (11)
H6	0.3334	1.1834	0.0788	0.030*
C7	0.4256 (6)	1.0005 (5)	0.1451 (3)	0.0228 (10)
H7	0.4803	1.0393	0.1828	0.027*
C8	0.4353 (6)	0.8596 (5)	0.1527 (3)	0.0197 (10)
C9	0.3486 (6)	0.8058 (4)	0.0956 (3)	0.0171 (9)
C10	0.7577 (6)	1.0063 (5)	0.4660 (3)	0.0208 (10)
C11	0.7396 (6)	0.9540 (5)	0.3939 (3)	0.0220 (10)
C12	0.6582 (6)	0.8283 (5)	0.4091 (3)	0.0238 (11)
H12	0.6452	0.7911	0.3614	0.029*
C13	0.5940 (6)	0.7539 (5)	0.4932 (3)	0.0254 (11)
H13	0.5399	0.6668	0.5013	0.030*
C14	0.6071 (6)	0.8030 (5)	0.5637 (3)	0.0251 (11)
H14	0.5609	0.7521	0.6203	0.030*
C15	0.6919 (6)	0.9330 (5)	0.5509 (3)	0.0226 (10)
C16	0.7117 (7)	0.9934 (5)	0.6198 (3)	0.0283 (11)
H16	0.6721	0.9455	0.6781	0.034*
C17	0.7881 (6)	1.1211 (5)	0.6025 (3)	0.0247 (11)
H17	0.7957	1.1629	0.6488	0.030*
C18	0.8548 (6)	1.1910 (5)	0.5179 (3)	0.0224 (10)
C19	0.9411 (6)	1.3281 (5)	0.4955 (4)	0.0278 (11)
H19A	0.9106	1.3840	0.4399	0.042*
H19B	1.0644	1.3150	0.4908	0.042*
H19C	0.9054	1.3758	0.5410	0.042*
C20	0.9683 (6)	0.8028 (5)	0.2200 (4)	0.0289 (12)
H20A	1.0752	0.8552	0.2092	0.043*
H20B	0.9763	0.7361	0.1843	0.043*
H20C	0.9470	0.7529	0.2816	0.043*
C21	0.9985 (7)	1.3030 (6)	0.2168 (3)	0.0319 (12)
H21A	0.8821	1.2724	0.2171	0.048*
H21B	1.0773	1.2565	0.1812	0.048*
H21C	1.0075	1.4037	0.1924	0.048*

	U11	U22	U33	U12	U13	U23
Sn1	0.0224 (2)	0.01323 (17)	0.0203 (2)	−0.00323 (12)	−0.00130 (14)	−0.00209 (13)
Cl1	0.0248 (6)	0.0189 (5)	0.0238 (6)	−0.0031 (4)	0.0030 (5)	−0.0041 (5)
Cl2	0.0291 (7)	0.0147 (5)	0.0277 (7)	−0.0021 (4)	−0.0006 (5)	−0.0045 (5)
Cl3	0.0291 (7)	0.0225 (6)	0.0245 (7)	−0.0029 (5)	−0.0066 (5)	0.0002 (5)
Cl4	0.0249 (6)	0.0167 (5)	0.0237 (6)	−0.0025 (4)	0.0021 (5)	−0.0028 (5)
O1	0.0243 (18)	0.0132 (15)	0.0230 (19)	−0.0003 (13)	−0.0024 (15)	−0.0039 (14)
O2	0.041 (2)	0.0218 (17)	0.0186 (19)	−0.0130 (15)	0.0025 (16)	−0.0020 (14)
O3	0.0248 (19)	0.0234 (17)	0.025 (2)	−0.0081 (14)	−0.0014 (15)	−0.0005 (15)
O4	0.030 (2)	0.0241 (18)	0.024 (2)	−0.0085 (14)	−0.0026 (15)	−0.0041 (15)
N1	0.018 (2)	0.0176 (19)	0.019 (2)	−0.0039 (15)	0.0008 (16)	−0.0001 (16)
N2	0.024 (2)	0.021 (2)	0.018 (2)	−0.0018 (16)	−0.0012 (17)	−0.0019 (17)
C1	0.027 (3)	0.015 (2)	0.025 (3)	−0.0030 (19)	0.004 (2)	−0.003 (2)
C2	0.029 (3)	0.029 (3)	0.019 (3)	−0.005 (2)	−0.002 (2)	−0.007 (2)
C3	0.022 (3)	0.020 (2)	0.018 (3)	0.0015 (18)	−0.002 (2)	0.0032 (19)
C4	0.022 (3)	0.019 (2)	0.020 (3)	−0.0034 (18)	0.006 (2)	−0.005 (2)
C5	0.022 (3)	0.019 (2)	0.021 (3)	0.0026 (19)	−0.002 (2)	0.000 (2)
C6	0.026 (3)	0.014 (2)	0.030 (3)	−0.0032 (19)	0.007 (2)	−0.001 (2)
C7	0.024 (3)	0.021 (2)	0.019 (3)	−0.0067 (19)	0.005 (2)	−0.002 (2)
C8	0.016 (2)	0.019 (2)	0.021 (3)	−0.0012 (18)	0.0017 (19)	−0.0030 (19)
C9	0.018 (2)	0.017 (2)	0.014 (2)	−0.0023 (17)	0.0039 (18)	−0.0025 (18)
C10	0.019 (3)	0.017 (2)	0.023 (3)	0.0003 (18)	0.000 (2)	−0.002 (2)
C11	0.023 (3)	0.020 (2)	0.022 (3)	−0.0006 (19)	−0.003 (2)	−0.003 (2)
C12	0.023 (3)	0.023 (2)	0.024 (3)	−0.0014 (19)	0.001 (2)	−0.005 (2)
C13	0.023 (3)	0.016 (2)	0.034 (3)	−0.0063 (19)	0.004 (2)	−0.002 (2)
C14	0.030 (3)	0.016 (2)	0.024 (3)	0.0005 (19)	0.002 (2)	0.003 (2)
C15	0.016 (2)	0.022 (2)	0.028 (3)	0.0051 (19)	−0.001 (2)	−0.005 (2)
C16	0.031 (3)	0.031 (3)	0.020 (3)	0.002 (2)	0.001 (2)	−0.003 (2)
C17	0.026 (3)	0.028 (3)	0.019 (3)	−0.001 (2)	−0.002 (2)	−0.005 (2)
C18	0.014 (2)	0.028 (3)	0.024 (3)	0.0036 (19)	−0.002 (2)	−0.004 (2)
C19	0.023 (3)	0.030 (3)	0.032 (3)	−0.002 (2)	−0.006 (2)	−0.011 (2)
C20	0.025 (3)	0.031 (3)	0.029 (3)	−0.002 (2)	−0.004 (2)	−0.005 (2)
C21	0.032 (3)	0.034 (3)	0.027 (3)	−0.004 (2)	−0.004 (2)	−0.002 (2)

Sn1—O1	2.075 (3)	C6—H6	0.9500
Sn1—N1	2.204 (4)	C7—C8	1.379 (6)
Sn1—Cl3	2.3758 (12)	C7—H7	0.9500
Sn1—Cl2	2.3898 (11)	C8—C9	1.428 (6)
Sn1—Cl4	2.4174 (12)	C10—C15	1.409 (7)
Sn1—Cl1	2.4427 (12)	C10—C11	1.412 (6)
O1—C8	1.350 (5)	C11—C12	1.376 (6)
O2—C11	1.333 (6)	C12—C13	1.399 (7)
O2—H2	0.8400	C12—H12	0.9500
O3—C20	1.423 (6)	C13—C14	1.361 (7)
O3—H3	0.8400	C13—H13	0.9500
O4—C21	1.426 (6)	C14—C15	1.431 (7)
O4—H4	0.8400	C14—H14	0.9500
N1—C1	1.328 (6)	C15—C16	1.416 (6)
N1—C9	1.381 (5)	C16—C17	1.371 (7)
N2—C18	1.341 (6)	C16—H16	0.9500
N2—C10	1.373 (6)	C17—C18	1.397 (7)
N2—H2N	0.8800	C17—H17	0.9500
C1—C2	1.400 (7)	C18—C19	1.483 (7)
C1—H1	0.9500	C19—H19A	0.9800
C2—C3	1.358 (6)	C19—H19B	0.9800
C2—H2A	0.9500	C19—H19C	0.9800
C3—C4	1.422 (6)	C20—H20A	0.9800
C3—H3A	0.9500	C20—H20B	0.9800
C4—C9	1.399 (7)	C20—H20C	0.9800
C4—C5	1.411 (6)	C21—H21A	0.9800
C5—C6	1.370 (6)	C21—H21B	0.9800
C5—H5	0.9500	C21—H21C	0.9800
C6—C7	1.393 (7)
O1—Sn1—N1	78.45 (12)	N1—C9—C4	121.7 (4)
O1—Sn1—Cl3	90.22 (9)	N1—C9—C8	116.6 (4)
N1—Sn1—Cl3	168.60 (9)	C4—C9—C8	121.7 (4)
O1—Sn1—Cl2	171.51 (9)	N2—C10—C15	119.3 (4)
N1—Sn1—Cl2	93.09 (10)	N2—C10—C11	119.7 (4)
Cl3—Sn1—Cl2	98.22 (4)	C15—C10—C11	121.0 (4)
O1—Sn1—Cl4	88.73 (9)	O2—C11—C12	125.8 (4)
N1—Sn1—Cl4	87.00 (10)	O2—C11—C10	116.2 (4)
Cl3—Sn1—Cl4	93.98 (4)	C12—C11—C10	118.0 (5)
Cl2—Sn1—Cl4	91.61 (4)	C11—C12—C13	121.5 (4)
O1—Sn1—Cl1	88.01 (9)	C11—C12—H12	119.3
N1—Sn1—Cl1	86.76 (10)	C13—C12—H12	119.3
Cl3—Sn1—Cl1	91.73 (4)	C14—C13—C12	121.7 (4)
Cl2—Sn1—Cl1	90.78 (4)	C14—C13—H13	119.1
Cl4—Sn1—Cl1	173.44 (4)	C12—C13—H13	119.1
C8—O1—Sn1	114.7 (2)	C13—C14—C15	118.7 (5)
C11—O2—H2	109.5	C13—C14—H14	120.7
C20—O3—H3	109.5	C15—C14—H14	120.7
C21—O4—H4	109.5	C10—C15—C16	117.8 (4)
C1—N1—C9	119.6 (4)	C10—C15—C14	119.1 (4)
C1—N1—Sn1	129.6 (3)	C16—C15—C14	123.1 (5)
C9—N1—Sn1	110.8 (3)	C17—C16—C15	120.0 (5)
C18—N2—C10	123.4 (4)	C17—C16—H16	120.0
C18—N2—H2N	118.3	C15—C16—H16	120.0
C10—N2—H2N	118.3	C16—C17—C18	121.2 (4)
N1—C1—C2	121.3 (4)	C16—C17—H17	119.4
N1—C1—H1	119.3	C18—C17—H17	119.4
C2—C1—H1	119.3	N2—C18—C17	118.2 (4)
C3—C2—C1	120.3 (4)	N2—C18—C19	118.2 (4)
C3—C2—H2A	119.8	C17—C18—C19	123.6 (4)
C1—C2—H2A	119.8	C18—C19—H19A	109.5
C2—C3—C4	119.8 (4)	C18—C19—H19B	109.5
C2—C3—H3A	120.1	H19A—C19—H19B	109.5
C4—C3—H3A	120.1	C18—C19—H19C	109.5
C9—C4—C5	118.5 (4)	H19A—C19—H19C	109.5
C9—C4—C3	117.2 (4)	H19B—C19—H19C	109.5
C5—C4—C3	124.3 (4)	O3—C20—H20A	109.5
C6—C5—C4	119.6 (4)	O3—C20—H20B	109.5
C6—C5—H5	120.2	H20A—C20—H20B	109.5
C4—C5—H5	120.2	O3—C20—H20C	109.5
C5—C6—C7	121.8 (4)	H20A—C20—H20C	109.5
C5—C6—H6	119.1	H20B—C20—H20C	109.5
C7—C6—H6	119.1	O4—C21—H21A	109.5
C8—C7—C6	120.9 (4)	O4—C21—H21B	109.5
C8—C7—H7	119.5	H21A—C21—H21B	109.5
C6—C7—H7	119.5	O4—C21—H21C	109.5
O1—C8—C7	123.1 (4)	H21A—C21—H21C	109.5
O1—C8—C9	119.4 (4)	H21B—C21—H21C	109.5
C7—C8—C9	117.5 (4)
N1—Sn1—O1—C8	1.6 (3)	C5—C4—C9—N1	−178.9 (4)
Cl3—Sn1—O1—C8	−177.2 (3)	C3—C4—C9—N1	0.3 (7)
Cl4—Sn1—O1—C8	88.8 (3)	C5—C4—C9—C8	−1.1 (7)
Cl1—Sn1—O1—C8	−85.5 (3)	C3—C4—C9—C8	178.1 (4)
O1—Sn1—N1—C1	178.1 (4)	O1—C8—C9—N1	−0.1 (6)
Cl3—Sn1—N1—C1	−175.9 (4)	C7—C8—C9—N1	179.2 (4)
Cl2—Sn1—N1—C1	−2.6 (4)	O1—C8—C9—C4	−178.0 (4)
Cl4—Sn1—N1—C1	88.8 (4)	C7—C8—C9—C4	1.3 (7)
Cl1—Sn1—N1—C1	−93.2 (4)	C18—N2—C10—C15	−2.4 (7)
O1—Sn1—N1—C9	−1.6 (3)	C18—N2—C10—C11	176.9 (4)
Cl3—Sn1—N1—C9	4.4 (7)	N2—C10—C11—O2	−1.5 (7)
Cl2—Sn1—N1—C9	177.6 (3)	C15—C10—C11—O2	177.8 (4)
Cl4—Sn1—N1—C9	−90.9 (3)	N2—C10—C11—C12	179.7 (4)
Cl1—Sn1—N1—C9	87.0 (3)	C15—C10—C11—C12	−1.0 (7)
C9—N1—C1—C2	0.0 (7)	O2—C11—C12—C13	−178.4 (5)
Sn1—N1—C1—C2	−179.7 (3)	C10—C11—C12—C13	0.3 (7)
N1—C1—C2—C3	0.7 (8)	C11—C12—C13—C14	0.8 (8)
C1—C2—C3—C4	−0.9 (8)	C12—C13—C14—C15	−1.2 (7)
C2—C3—C4—C9	0.4 (7)	N2—C10—C15—C16	0.7 (7)
C2—C3—C4—C5	179.5 (5)	C11—C10—C15—C16	−178.7 (4)
C9—C4—C5—C6	0.7 (7)	N2—C10—C15—C14	179.9 (4)
C3—C4—C5—C6	−178.5 (5)	C11—C10—C15—C14	0.6 (7)
C4—C5—C6—C7	−0.5 (8)	C13—C14—C15—C10	0.5 (7)
C5—C6—C7—C8	0.7 (8)	C13—C14—C15—C16	179.7 (5)
Sn1—O1—C8—C7	179.3 (4)	C10—C15—C16—C17	2.0 (7)
Sn1—O1—C8—C9	−1.4 (5)	C14—C15—C16—C17	−177.2 (5)
C6—C7—C8—O1	178.2 (4)	C15—C16—C17—C18	−3.1 (7)
C6—C7—C8—C9	−1.1 (7)	C10—N2—C18—C17	1.4 (7)
C1—N1—C9—C4	−0.5 (7)	C10—N2—C18—C19	−178.2 (4)
Sn1—N1—C9—C4	179.3 (4)	C16—C17—C18—N2	1.4 (7)
C1—N1—C9—C8	−178.4 (4)	C16—C17—C18—C19	−179.0 (4)
Sn1—N1—C9—C8	1.4 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3	0.84	1.76	2.595 (4)	172
O3—H3···O1	0.84	1.91	2.736 (4)	168
O4—H4···Cl1i	0.84	2.53	3.258 (3)	146
N2—H2n···O4	0.88	1.91	2.764 (5)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3	0.84	1.76	2.595 (4)	172
O3—H3⋯O1	0.84	1.91	2.736 (4)	168
O4—H4⋯Cl1i	0.84	2.53	3.258 (3)	146
N2—H2n⋯O4	0.88	1.91	2.764 (5)	162

Symmetry code: (i) .