8-Hy-droxy-2-methyl-quinolinium tetra-chlorido(quinolin-8-olato-κ(2)N,O)stan-nate(IV).

The reaction of 8-hy-droxy-quinoline, 2-methyl-quinolin-8-ol and stannic chloride yields the protonated 8-hy-droxy-2-methyl-quinolinium species. In the title salt, (C(10)H(10)NO)[Sn(C(9)H(6)NO)Cl(4)], the Sn(IV) cation is N,O-chelated by the quinolin-8-olate anion and is further coordinated by four Cl(-) anions in a distorted cis-SnNOCl(4) octa-hedral geometry. In the crystal, the cation is linked to the anion by an O-H⋯O hydrogen bond.

Related literature

For the methanol solvate of the salt, see: Najafi et al. (2011 ▶).

Experimental

Crystal data

(C10H10NO)[Sn(C9H6NO)Cl4]

M = 564.83

Monoclinic,

a = 8.9431 (3) Å

b = 11.5892 (4) Å

c = 20.1795 (8) Å

β = 101.347 (4)°

V = 2050.59 (13) Å3

Z = 4

Mo Kα radiation

μ = 1.79 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, 2012 ▶) T min = 0.616, T max = 0.717

13674 measured reflections

4723 independent reflections

4222 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.055

S = 1.06

4723 reflections

262 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 e Å−3

Δρmin = −0.54 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536812019459/xu5531sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019459/xu5531Isup2.hkl

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

(C10H10NO)[Sn(C9H6NO)Cl4]	F(000) = 1112
Mr = 564.83	Dx = 1.830 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6840 reflections
a = 8.9431 (3) Å	θ = 2.3–27.5°
b = 11.5892 (4) Å	µ = 1.79 mm−1
c = 20.1795 (8) Å	T = 100 K
β = 101.347 (4)°	Prism, yellow
V = 2050.59 (13) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	4723 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4222 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.029
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.3°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −14→15
Tmin = 0.616, Tmax = 0.717	l = −17→26
13674 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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.055	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0193P)2 + 1.171P] where P = (Fo2 + 2Fc2)/3
4723 reflections	(Δ/σ)max = 0.001
262 parameters	Δρmax = 0.48 e Å−3
2 restraints	Δρmin = −0.54 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.252394 (17)	0.454836 (13)	0.684298 (7)	0.01219 (5)
Cl1	0.06888 (7)	0.32750 (5)	0.71370 (3)	0.01978 (13)
Cl2	0.36818 (7)	0.51365 (5)	0.79638 (3)	0.01813 (12)
Cl3	0.43713 (6)	0.30303 (5)	0.68659 (3)	0.01751 (12)
Cl4	0.07496 (7)	0.61568 (5)	0.67319 (3)	0.01740 (12)
O1	0.17767 (18)	0.42497 (13)	0.58138 (8)	0.0149 (3)
O2	0.0249 (2)	0.25623 (14)	0.50577 (9)	0.0221 (4)
N1	0.4033 (2)	0.56783 (15)	0.63929 (10)	0.0141 (4)
N2	−0.0535 (2)	0.12664 (17)	0.39515 (10)	0.0161 (4)
C1	0.5172 (3)	0.6332 (2)	0.66989 (12)	0.0188 (5)
H1A	0.5461	0.6301	0.7177	0.023*
C2	0.5963 (3)	0.7065 (2)	0.63406 (13)	0.0224 (6)
H2A	0.6782	0.7523	0.6572	0.027*
C3	0.5545 (3)	0.7115 (2)	0.56511 (13)	0.0227 (5)
H3	0.6070	0.7618	0.5403	0.027*
C4	0.4339 (3)	0.6427 (2)	0.53060 (12)	0.0186 (5)
C5	0.3821 (3)	0.6417 (2)	0.45981 (13)	0.0228 (6)
H5	0.4297	0.6892	0.4316	0.027*
C6	0.2630 (3)	0.5720 (2)	0.43221 (12)	0.0227 (6)
H6	0.2276	0.5730	0.3846	0.027*
C7	0.1908 (3)	0.4985 (2)	0.47190 (12)	0.0187 (5)
H7	0.1084	0.4511	0.4509	0.022*
C8	0.2391 (3)	0.4952 (2)	0.54069 (11)	0.0145 (5)
C9	0.3609 (3)	0.56980 (19)	0.57047 (11)	0.0147 (5)
C10	−0.2450 (3)	0.1085 (2)	0.29236 (13)	0.0254 (6)
H10A	−0.2408	0.1929	0.2898	0.038*
H10B	−0.3371	0.0854	0.3084	0.038*
H10C	−0.2472	0.0756	0.2474	0.038*
C11	−0.1082 (3)	0.0656 (2)	0.34005 (12)	0.0178 (5)
C12	−0.0360 (3)	−0.0387 (2)	0.33034 (12)	0.0197 (5)
H12	−0.0737	−0.0843	0.2915	0.024*
C13	0.0878 (3)	−0.0750 (2)	0.37615 (12)	0.0193 (5)
H13	0.1363	−0.1454	0.3687	0.023*
C14	0.1453 (3)	−0.0089 (2)	0.43484 (12)	0.0176 (5)
C15	0.2728 (3)	−0.0407 (2)	0.48462 (13)	0.0215 (5)
H15	0.3271	−0.1096	0.4797	0.026*
C16	0.3176 (3)	0.0281 (2)	0.53985 (13)	0.0227 (6)
H16	0.4045	0.0069	0.5728	0.027*
C17	0.2382 (3)	0.1294 (2)	0.54906 (12)	0.0198 (5)
H17	0.2709	0.1751	0.5883	0.024*
C18	0.1135 (3)	0.1629 (2)	0.50175 (12)	0.0169 (5)
C19	0.0689 (3)	0.0939 (2)	0.44380 (11)	0.0153 (5)
H1	0.071 (3)	0.303 (2)	0.5341 (12)	0.036 (9)*
H2	−0.099 (3)	0.1922 (13)	0.4000 (13)	0.020 (7)*

	U11	U22	U33	U12	U13	U23
Sn1	0.01472 (9)	0.01041 (8)	0.01115 (8)	−0.00037 (6)	0.00186 (6)	−0.00024 (6)
Cl1	0.0212 (3)	0.0150 (3)	0.0243 (3)	−0.0044 (2)	0.0074 (2)	0.0002 (2)
Cl2	0.0193 (3)	0.0214 (3)	0.0131 (3)	−0.0001 (2)	0.0016 (2)	−0.0029 (2)
Cl3	0.0196 (3)	0.0159 (3)	0.0163 (3)	0.0045 (2)	0.0019 (2)	−0.0001 (2)
Cl4	0.0208 (3)	0.0137 (3)	0.0176 (3)	0.0038 (2)	0.0036 (2)	0.0006 (2)
O1	0.0173 (8)	0.0144 (8)	0.0127 (8)	−0.0002 (7)	0.0025 (6)	−0.0007 (6)
O2	0.0236 (9)	0.0169 (9)	0.0246 (10)	−0.0012 (8)	0.0018 (8)	−0.0085 (7)
N1	0.0170 (10)	0.0106 (9)	0.0152 (10)	0.0006 (8)	0.0046 (8)	−0.0003 (7)
N2	0.0163 (10)	0.0128 (10)	0.0194 (10)	0.0002 (8)	0.0039 (8)	−0.0004 (8)
C1	0.0201 (12)	0.0167 (12)	0.0197 (12)	−0.0029 (10)	0.0043 (10)	−0.0036 (10)
C2	0.0200 (12)	0.0164 (12)	0.0318 (15)	−0.0059 (10)	0.0075 (11)	−0.0050 (10)
C3	0.0224 (13)	0.0179 (12)	0.0321 (15)	−0.0005 (11)	0.0156 (11)	0.0025 (11)
C4	0.0205 (12)	0.0149 (11)	0.0225 (13)	0.0066 (10)	0.0092 (10)	0.0022 (10)
C5	0.0290 (14)	0.0208 (13)	0.0220 (13)	0.0088 (11)	0.0131 (11)	0.0060 (10)
C6	0.0294 (14)	0.0257 (14)	0.0135 (12)	0.0127 (12)	0.0056 (10)	0.0026 (10)
C7	0.0181 (12)	0.0202 (12)	0.0166 (12)	0.0051 (10)	0.0003 (9)	−0.0013 (10)
C8	0.0159 (11)	0.0118 (10)	0.0162 (11)	0.0050 (9)	0.0041 (9)	0.0008 (9)
C9	0.0168 (11)	0.0120 (11)	0.0158 (11)	0.0061 (9)	0.0047 (9)	0.0017 (9)
C10	0.0208 (13)	0.0287 (15)	0.0239 (14)	−0.0040 (11)	−0.0022 (11)	−0.0005 (11)
C11	0.0174 (12)	0.0183 (12)	0.0181 (12)	−0.0069 (10)	0.0044 (10)	0.0001 (9)
C12	0.0251 (13)	0.0186 (12)	0.0176 (12)	−0.0066 (11)	0.0098 (10)	−0.0050 (9)
C13	0.0238 (13)	0.0143 (11)	0.0219 (13)	−0.0006 (10)	0.0096 (10)	−0.0012 (10)
C14	0.0201 (12)	0.0163 (11)	0.0182 (12)	−0.0028 (10)	0.0083 (10)	0.0014 (9)
C15	0.0211 (13)	0.0201 (13)	0.0243 (13)	0.0026 (11)	0.0066 (11)	0.0048 (10)
C16	0.0194 (12)	0.0278 (14)	0.0198 (13)	−0.0032 (11)	0.0008 (10)	0.0061 (11)
C17	0.0214 (12)	0.0226 (13)	0.0154 (12)	−0.0093 (11)	0.0036 (10)	−0.0012 (10)
C18	0.0183 (12)	0.0144 (11)	0.0188 (12)	−0.0056 (10)	0.0061 (9)	−0.0007 (9)
C19	0.0145 (11)	0.0171 (11)	0.0152 (11)	−0.0047 (10)	0.0052 (9)	0.0016 (9)

Sn1—O1	2.0818 (15)	C6—C7	1.409 (4)
Sn1—N1	2.201 (2)	C6—H6	0.9500
Sn1—Cl1	2.3678 (6)	C7—C8	1.371 (3)
Sn1—Cl2	2.3938 (6)	C7—H7	0.9500
Sn1—Cl3	2.4076 (6)	C8—C9	1.427 (3)
Sn1—Cl4	2.4296 (6)	C10—C11	1.486 (3)
O1—C8	1.348 (3)	C10—H10A	0.9800
O2—C18	1.353 (3)	C10—H10B	0.9800
O2—H1	0.835 (10)	C10—H10C	0.9800
N1—C1	1.321 (3)	C11—C12	1.402 (3)
N1—C9	1.366 (3)	C12—C13	1.362 (3)
N2—C11	1.328 (3)	C12—H12	0.9500
N2—C19	1.372 (3)	C13—C14	1.419 (3)
N2—H2	0.878 (10)	C13—H13	0.9500
C1—C2	1.395 (3)	C14—C19	1.402 (3)
C1—H1A	0.9500	C14—C15	1.412 (3)
C2—C3	1.369 (4)	C15—C16	1.364 (4)
C2—H2A	0.9500	C15—H15	0.9500
C3—C4	1.411 (3)	C16—C17	1.404 (4)
C3—H3	0.9500	C16—H16	0.9500
C4—C9	1.411 (3)	C17—C18	1.373 (3)
C4—C5	1.412 (3)	C17—H17	0.9500
C5—C6	1.365 (4)	C18—C19	1.408 (3)
C5—H5	0.9500
O1—Sn1—N1	77.86 (7)	C8—C7—H7	119.9
O1—Sn1—Cl1	92.52 (5)	C6—C7—H7	119.9
N1—Sn1—Cl1	170.33 (5)	O1—C8—C7	123.2 (2)
O1—Sn1—Cl2	169.80 (5)	O1—C8—C9	118.6 (2)
N1—Sn1—Cl2	91.96 (5)	C7—C8—C9	118.2 (2)
Cl1—Sn1—Cl2	97.65 (2)	N1—C9—C4	121.5 (2)
O1—Sn1—Cl3	88.97 (5)	N1—C9—C8	117.0 (2)
N1—Sn1—Cl3	88.20 (5)	C4—C9—C8	121.5 (2)
Cl1—Sn1—Cl3	92.67 (2)	C11—C10—H10A	109.5
Cl2—Sn1—Cl3	91.28 (2)	C11—C10—H10B	109.5
O1—Sn1—Cl4	87.70 (4)	H10A—C10—H10B	109.5
N1—Sn1—Cl4	87.00 (5)	C11—C10—H10C	109.5
Cl1—Sn1—Cl4	91.66 (2)	H10A—C10—H10C	109.5
Cl2—Sn1—Cl4	91.26 (2)	H10B—C10—H10C	109.5
Cl3—Sn1—Cl4	174.65 (2)	N2—C11—C12	118.2 (2)
C8—O1—Sn1	114.70 (13)	N2—C11—C10	119.0 (2)
C18—O2—H1	110 (2)	C12—C11—C10	122.8 (2)
C1—N1—C9	120.0 (2)	C13—C12—C11	120.5 (2)
C1—N1—Sn1	128.84 (16)	C13—C12—H12	119.8
C9—N1—Sn1	111.09 (14)	C11—C12—H12	119.8
C11—N2—C19	124.2 (2)	C12—C13—C14	120.8 (2)
C11—N2—H2	116.8 (16)	C12—C13—H13	119.6
C19—N2—H2	119.0 (17)	C14—C13—H13	119.6
N1—C1—C2	122.0 (2)	C19—C14—C15	118.4 (2)
N1—C1—H1A	119.0	C19—C14—C13	117.4 (2)
C2—C1—H1A	119.0	C15—C14—C13	124.2 (2)
C3—C2—C1	119.2 (2)	C16—C15—C14	119.7 (2)
C3—C2—H2A	120.4	C16—C15—H15	120.2
C1—C2—H2A	120.4	C14—C15—H15	120.2
C2—C3—C4	120.5 (2)	C15—C16—C17	121.4 (2)
C2—C3—H3	119.8	C15—C16—H16	119.3
C4—C3—H3	119.8	C17—C16—H16	119.3
C3—C4—C9	116.8 (2)	C18—C17—C16	120.5 (2)
C3—C4—C5	124.8 (2)	C18—C17—H17	119.8
C9—C4—C5	118.4 (2)	C16—C17—H17	119.8
C6—C5—C4	119.4 (2)	O2—C18—C17	126.1 (2)
C6—C5—H5	120.3	O2—C18—C19	115.5 (2)
C4—C5—H5	120.3	C17—C18—C19	118.4 (2)
C5—C6—C7	122.2 (2)	N2—C19—C14	118.9 (2)
C5—C6—H6	118.9	N2—C19—C18	119.5 (2)
C7—C6—H6	118.9	C14—C19—C18	121.6 (2)
C8—C7—C6	120.2 (2)
N1—Sn1—O1—C8	−7.95 (15)	C3—C4—C9—N1	1.3 (3)
Cl1—Sn1—O1—C8	171.04 (14)	C5—C4—C9—N1	−178.8 (2)
Cl2—Sn1—O1—C8	−4.8 (4)	C3—C4—C9—C8	−179.0 (2)
Cl3—Sn1—O1—C8	−96.33 (14)	C5—C4—C9—C8	0.9 (3)
Cl4—Sn1—O1—C8	79.48 (14)	O1—C8—C9—N1	−2.5 (3)
O1—Sn1—N1—C1	−176.9 (2)	C7—C8—C9—N1	177.7 (2)
Cl2—Sn1—N1—C1	3.69 (19)	O1—C8—C9—C4	177.8 (2)
Cl3—Sn1—N1—C1	−87.52 (19)	C7—C8—C9—C4	−2.0 (3)
Cl4—Sn1—N1—C1	94.85 (19)	C19—N2—C11—C12	−0.6 (4)
O1—Sn1—N1—C9	6.51 (14)	C19—N2—C11—C10	177.8 (2)
Cl2—Sn1—N1—C9	−172.94 (14)	N2—C11—C12—C13	−0.6 (4)
Cl3—Sn1—N1—C9	95.84 (14)	C10—C11—C12—C13	−179.0 (2)
Cl4—Sn1—N1—C9	−81.79 (14)	C11—C12—C13—C14	0.6 (4)
C9—N1—C1—C2	0.8 (3)	C12—C13—C14—C19	0.6 (4)
Sn1—N1—C1—C2	−175.60 (17)	C12—C13—C14—C15	179.9 (2)
N1—C1—C2—C3	0.3 (4)	C19—C14—C15—C16	0.4 (4)
C1—C2—C3—C4	−0.6 (4)	C13—C14—C15—C16	−178.9 (2)
C2—C3—C4—C9	−0.1 (3)	C14—C15—C16—C17	1.1 (4)
C2—C3—C4—C5	179.9 (2)	C15—C16—C17—C18	−0.9 (4)
C3—C4—C5—C6	−179.4 (2)	C16—C17—C18—O2	177.8 (2)
C9—C4—C5—C6	0.7 (3)	C16—C17—C18—C19	−0.6 (4)
C4—C5—C6—C7	−1.2 (4)	C11—N2—C19—C14	1.9 (4)
C5—C6—C7—C8	0.1 (4)	C11—N2—C19—C18	−177.3 (2)
Sn1—O1—C8—C7	−171.77 (18)	C15—C14—C19—N2	178.8 (2)
Sn1—O1—C8—C9	8.4 (3)	C13—C14—C19—N2	−1.8 (3)
C6—C7—C8—O1	−178.3 (2)	C15—C14—C19—C18	−2.0 (4)
C6—C7—C8—C9	1.5 (3)	C13—C14—C19—C18	177.4 (2)
C1—N1—C9—C4	−1.6 (3)	O2—C18—C19—N2	2.7 (3)
Sn1—N1—C9—C4	175.39 (17)	C17—C18—C19—N2	−178.7 (2)
C1—N1—C9—C8	178.7 (2)	O2—C18—C19—C14	−176.5 (2)
Sn1—N1—C9—C8	−4.3 (2)	C17—C18—C19—C14	2.1 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1···O1	0.84 (1)	1.86 (1)	2.683 (2)	168 (3)
N2—H2···O2	0.88 (1)	2.33 (2)	2.667 (3)	103 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1⋯O1	0.84 (1)	1.86 (1)	2.683 (2)	168 (3)