10-Hy-droxy-benzo[h]quinolin-1-ium tetra-chlorido(pyridine-2-carboxyl-ato-κ(2)N,O)stannate(IV) methanol monosolvate.

The reaction of 4-(dimethyl-amino)-pyridine, picolinic acid and stannic chloride yields the title monosolvated salt, (C(13)H(10)NO)[SnCl(4)(C(6)H(4)NO(2))]·CH(3)OH. The Sn(IV) atom is N,O-chelated by the picolinate ion in a cis-SnNOCl(4) octa-hedral geometry. The cation is linked to the methanol solvent mol-ecule by an O-H⋯O hydrogen bond; the solvent mol-ecule itself is a hydrogen-bond donor to the uncoordinating carboxyl-ate O atom of the anion. The cations and anions are linked by weak N-H⋯Cl inter-actions, forming a chain running along the b axis.

Related literature

For a tetra­chlorido(pyridine-2-carboxyl­ato)stannate(IV), see: Najafi et al. (2012 ▶).

Experimental

Crystal data

(C13H10NO)[SnCl4(C6H4NO2)]·CH4O

M = 610.85

Monoclinic,

a = 31.5065 (11) Å

b = 8.0802 (2) Å

c = 20.0948 (9) Å

β = 115.722 (5)°

V = 4608.8 (3) Å3

Z = 8

Mo Kα radiation

μ = 1.60 mm−1

T = 100 K

0.30 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) ▶ T min = 0.645, T max = 0.856

15316 measured reflections

5326 independent reflections

4445 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.065

S = 1.02

5326 reflections

293 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.51 e Å−3

Δρmin = −0.44 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/S1600536812019605/hg5222sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019605/hg5222Isup2.hkl

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

(C13H10NO)[SnCl4(C6H4NO2)]·CH4O	F(000) = 2416
Mr = 610.85	Dx = 1.761 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 6804 reflections
a = 31.5065 (11) Å	θ = 2.6–27.5°
b = 8.0802 (2) Å	µ = 1.60 mm−1
c = 20.0948 (9) Å	T = 100 K
β = 115.722 (5)°	Prism, yellow
V = 4608.8 (3) Å3	0.30 × 0.20 × 0.10 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	5326 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4445 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.033
Detector resolution: 10.4041 pixels mm-1	θmax = 27.6°, θmin = 2.6°
ω scan	h = −29→40
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→10
Tmin = 0.645, Tmax = 0.856	l = −26→16
15316 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.065	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0262P)2 + 2.9883P] where P = (Fo2 + 2Fc2)/3
5326 reflections	(Δ/σ)max = 0.001
293 parameters	Δρmax = 0.51 e Å−3
3 restraints	Δρmin = −0.44 e Å−3

	x	y	z	Uiso*/Ueq
Sn1	0.341644 (5)	0.660077 (19)	0.666671 (10)	0.01289 (6)
Cl1	0.37922 (2)	0.39689 (7)	0.68079 (4)	0.02026 (14)
Cl2	0.40850 (2)	0.82509 (7)	0.68449 (4)	0.02084 (15)
Cl3	0.31336 (2)	0.66098 (8)	0.53578 (4)	0.02510 (15)
Cl4	0.36197 (2)	0.66555 (8)	0.79760 (4)	0.02179 (15)
O1	0.27693 (5)	0.5575 (2)	0.65110 (10)	0.0169 (4)
O2	0.20485 (6)	0.6113 (2)	0.64027 (11)	0.0225 (4)
O3	0.07905 (6)	0.2706 (2)	0.53486 (11)	0.0217 (4)
O4	0.16051 (6)	0.3577 (2)	0.54923 (12)	0.0238 (4)
N1	0.29836 (7)	0.8782 (2)	0.66282 (12)	0.0144 (4)
N2	0.02661 (7)	0.1368 (3)	0.58997 (13)	0.0172 (5)
C1	0.24389 (8)	0.6557 (3)	0.64886 (14)	0.0153 (5)
C2	0.25594 (8)	0.8378 (3)	0.65863 (14)	0.0148 (5)
C3	0.22558 (9)	0.9549 (3)	0.66296 (15)	0.0191 (6)
H3A	0.1957	0.9238	0.6599	0.023*
C4	0.23938 (9)	1.1189 (3)	0.67188 (16)	0.0215 (6)
H4A	0.2192	1.2022	0.6753	0.026*
C5	0.28285 (10)	1.1601 (3)	0.67575 (18)	0.0253 (7)
H5	0.2928	1.2723	0.6813	0.030*
C6	0.31165 (9)	1.0370 (3)	0.67148 (16)	0.0209 (6)
H6	0.3418	1.0654	0.6748	0.025*
C7	0.02266 (9)	0.0482 (3)	0.64277 (15)	0.0200 (6)
H7	0.0501	0.0137	0.6846	0.024*
C8	−0.02144 (9)	0.0061 (3)	0.63690 (16)	0.0207 (6)
H8	−0.0246	−0.0580	0.6741	0.025*
C9	−0.06052 (9)	0.0593 (3)	0.57607 (16)	0.0192 (6)
H9	−0.0910	0.0315	0.5714	0.023*
C10	−0.05622 (9)	0.1538 (3)	0.52073 (15)	0.0173 (5)
C11	−0.09634 (9)	0.2137 (3)	0.45798 (16)	0.0214 (6)
H11	−0.1271	0.1894	0.4528	0.026*
C12	−0.09079 (9)	0.3046 (3)	0.40608 (16)	0.0228 (6)
H12	−0.1180	0.3440	0.3650	0.027*
C13	−0.04506 (9)	0.3436 (3)	0.41098 (15)	0.0191 (6)
C14	−0.04056 (9)	0.4373 (3)	0.35614 (16)	0.0236 (6)
H14	−0.0680	0.4748	0.3149	0.028*
C15	0.00334 (9)	0.4759 (3)	0.36123 (16)	0.0240 (6)
H15	0.0059	0.5400	0.3235	0.029*
C16	0.04405 (9)	0.4220 (3)	0.42113 (16)	0.0208 (6)
H16	0.0741	0.4495	0.4240	0.025*
C17	0.04076 (9)	0.3285 (3)	0.47630 (15)	0.0172 (5)
C18	−0.00405 (9)	0.2878 (3)	0.47287 (15)	0.0166 (5)
C19	−0.01061 (8)	0.1925 (3)	0.52815 (15)	0.0153 (5)
C20	0.18022 (11)	0.3508 (4)	0.49717 (18)	0.0330 (7)
H20A	0.1712	0.4503	0.4662	0.050*
H20B	0.1683	0.2525	0.4659	0.050*
H20C	0.2146	0.3448	0.5237	0.050*
H2	0.0542 (6)	0.171 (3)	0.5956 (17)	0.027 (8)*
H3	0.1041 (7)	0.306 (4)	0.5351 (19)	0.042 (10)*
H4	0.1730 (9)	0.434 (2)	0.5790 (13)	0.021 (8)*

	U11	U22	U33	U12	U13	U23
Sn1	0.01130 (9)	0.01287 (9)	0.01497 (11)	−0.00094 (7)	0.00613 (7)	−0.00093 (7)
Cl1	0.0175 (3)	0.0155 (3)	0.0278 (4)	0.0006 (3)	0.0098 (3)	−0.0006 (3)
Cl2	0.0182 (3)	0.0206 (3)	0.0289 (4)	−0.0060 (3)	0.0151 (3)	−0.0059 (3)
Cl3	0.0224 (3)	0.0360 (4)	0.0157 (4)	0.0055 (3)	0.0071 (3)	−0.0004 (3)
Cl4	0.0147 (3)	0.0370 (4)	0.0143 (3)	0.0024 (3)	0.0068 (3)	0.0010 (3)
O1	0.0114 (8)	0.0143 (8)	0.0242 (11)	−0.0025 (7)	0.0072 (8)	−0.0018 (7)
O2	0.0135 (9)	0.0271 (10)	0.0276 (12)	−0.0053 (8)	0.0096 (9)	−0.0072 (9)
O3	0.0120 (9)	0.0288 (10)	0.0226 (12)	−0.0037 (8)	0.0058 (8)	0.0051 (8)
O4	0.0198 (10)	0.0308 (11)	0.0220 (12)	−0.0108 (9)	0.0101 (9)	−0.0093 (9)
N1	0.0184 (10)	0.0129 (10)	0.0136 (12)	0.0004 (9)	0.0084 (9)	0.0013 (9)
N2	0.0138 (10)	0.0201 (11)	0.0179 (13)	−0.0030 (9)	0.0070 (10)	−0.0010 (9)
C1	0.0141 (12)	0.0193 (12)	0.0118 (14)	−0.0012 (10)	0.0050 (11)	−0.0017 (10)
C2	0.0147 (12)	0.0179 (12)	0.0106 (13)	−0.0003 (10)	0.0045 (11)	−0.0011 (10)
C3	0.0147 (12)	0.0247 (14)	0.0179 (15)	0.0033 (11)	0.0069 (11)	0.0009 (11)
C4	0.0242 (14)	0.0214 (13)	0.0218 (17)	0.0083 (12)	0.0128 (13)	0.0048 (12)
C5	0.0342 (16)	0.0137 (13)	0.0355 (19)	0.0010 (12)	0.0221 (15)	0.0026 (12)
C6	0.0221 (13)	0.0178 (12)	0.0293 (18)	−0.0016 (11)	0.0173 (13)	0.0020 (11)
C7	0.0200 (13)	0.0223 (13)	0.0164 (15)	−0.0016 (11)	0.0067 (12)	−0.0002 (11)
C8	0.0215 (13)	0.0229 (13)	0.0198 (16)	−0.0015 (12)	0.0110 (12)	0.0002 (12)
C9	0.0161 (12)	0.0232 (13)	0.0221 (16)	−0.0039 (11)	0.0118 (12)	−0.0057 (11)
C10	0.0161 (12)	0.0194 (13)	0.0168 (15)	−0.0009 (11)	0.0074 (11)	−0.0043 (11)
C11	0.0118 (12)	0.0288 (14)	0.0238 (17)	−0.0021 (11)	0.0079 (12)	−0.0063 (12)
C12	0.0153 (13)	0.0290 (14)	0.0182 (16)	0.0006 (11)	0.0017 (12)	0.0000 (12)
C13	0.0180 (13)	0.0210 (13)	0.0167 (15)	−0.0010 (11)	0.0062 (12)	−0.0013 (11)
C14	0.0186 (13)	0.0282 (15)	0.0191 (16)	0.0016 (12)	0.0036 (12)	0.0033 (12)
C15	0.0261 (14)	0.0266 (14)	0.0183 (16)	−0.0019 (12)	0.0087 (13)	0.0041 (12)
C16	0.0175 (13)	0.0250 (14)	0.0217 (17)	−0.0048 (11)	0.0101 (12)	−0.0027 (12)
C17	0.0152 (12)	0.0174 (12)	0.0163 (15)	−0.0022 (10)	0.0044 (11)	−0.0035 (11)
C18	0.0155 (12)	0.0159 (12)	0.0169 (15)	−0.0036 (10)	0.0056 (11)	−0.0038 (11)
C19	0.0134 (12)	0.0160 (12)	0.0150 (14)	−0.0023 (10)	0.0047 (11)	−0.0046 (10)
C20	0.0347 (17)	0.0435 (18)	0.0256 (19)	−0.0095 (14)	0.0175 (15)	−0.0087 (14)

Sn1—O1	2.0949 (15)	C7—C8	1.385 (3)
Sn1—N1	2.2092 (19)	C7—H7	0.9500
Sn1—Cl3	2.3828 (7)	C8—C9	1.374 (4)
Sn1—Cl2	2.3851 (6)	C8—H8	0.9500
Sn1—Cl1	2.3903 (6)	C9—C10	1.403 (4)
Sn1—Cl4	2.4231 (7)	C9—H9	0.9500
O1—C1	1.294 (3)	C10—C19	1.414 (3)
O2—C1	1.220 (3)	C10—C11	1.428 (4)
O3—C17	1.352 (3)	C11—C12	1.347 (4)
O3—H3	0.835 (10)	C11—H11	0.9500
O4—C20	1.431 (3)	C12—C13	1.436 (3)
O4—H4	0.831 (10)	C12—H12	0.9500
N1—C6	1.338 (3)	C13—C14	1.394 (4)
N1—C2	1.342 (3)	C13—C18	1.423 (4)
N2—C7	1.330 (3)	C14—C15	1.377 (3)
N2—C19	1.363 (3)	C14—H14	0.9500
N2—H2	0.870 (10)	C15—C16	1.394 (4)
C1—C2	1.511 (3)	C15—H15	0.9500
C2—C3	1.375 (3)	C16—C17	1.382 (4)
C3—C4	1.381 (4)	C16—H16	0.9500
C3—H3A	0.9500	C17—C18	1.422 (3)
C4—C5	1.378 (4)	C18—C19	1.438 (3)
C4—H4A	0.9500	C20—H20A	0.9800
C5—C6	1.373 (3)	C20—H20B	0.9800
C5—H5	0.9500	C20—H20C	0.9800
C6—H6	0.9500
O1—Sn1—N1	76.37 (7)	C8—C7—H7	119.9
O1—Sn1—Cl3	87.87 (5)	C9—C8—C7	118.5 (2)
N1—Sn1—Cl3	91.69 (6)	C9—C8—H8	120.7
O1—Sn1—Cl2	169.28 (5)	C7—C8—H8	120.7
N1—Sn1—Cl2	92.91 (5)	C8—C9—C10	121.2 (2)
Cl3—Sn1—Cl2	92.68 (2)	C8—C9—H9	119.4
O1—Sn1—Cl1	93.77 (5)	C10—C9—H9	119.4
N1—Sn1—Cl1	168.64 (5)	C9—C10—C19	118.7 (2)
Cl3—Sn1—Cl1	93.58 (2)	C9—C10—C11	122.1 (2)
Cl2—Sn1—Cl1	96.88 (2)	C19—C10—C11	119.2 (2)
O1—Sn1—Cl4	87.18 (5)	C12—C11—C10	120.4 (2)
N1—Sn1—Cl4	83.78 (6)	C12—C11—H11	119.8
Cl3—Sn1—Cl4	173.96 (2)	C10—C11—H11	119.8
Cl2—Sn1—Cl4	91.54 (2)	C11—C12—C13	122.0 (3)
Cl1—Sn1—Cl4	90.20 (2)	C11—C12—H12	119.0
C1—O1—Sn1	118.61 (15)	C13—C12—H12	119.0
C17—O3—H3	112 (2)	C14—C13—C18	119.9 (2)
C20—O4—H4	109.5 (19)	C14—C13—C12	120.6 (2)
C6—N1—C2	119.2 (2)	C18—C13—C12	119.6 (2)
C6—N1—Sn1	127.39 (16)	C15—C14—C13	120.5 (3)
C2—N1—Sn1	113.00 (15)	C15—C14—H14	119.8
C7—N2—C19	124.3 (2)	C13—C14—H14	119.8
C7—N2—H2	120 (2)	C14—C15—C16	120.8 (3)
C19—N2—H2	115 (2)	C14—C15—H15	119.6
O2—C1—O1	124.9 (2)	C16—C15—H15	119.6
O2—C1—C2	119.1 (2)	C17—C16—C15	120.1 (2)
O1—C1—C2	116.1 (2)	C17—C16—H16	119.9
N1—C2—C3	122.0 (2)	C15—C16—H16	119.9
N1—C2—C1	115.6 (2)	O3—C17—C16	122.6 (2)
C3—C2—C1	122.4 (2)	O3—C17—C18	117.0 (2)
C2—C3—C4	118.7 (2)	C16—C17—C18	120.4 (2)
C2—C3—H3A	120.7	C17—C18—C13	118.4 (2)
C4—C3—H3A	120.7	C17—C18—C19	124.0 (2)
C5—C4—C3	119.2 (2)	C13—C18—C19	117.7 (2)
C5—C4—H4A	120.4	N2—C19—C10	117.1 (2)
C3—C4—H4A	120.4	N2—C19—C18	121.7 (2)
C6—C5—C4	119.3 (2)	C10—C19—C18	121.1 (2)
C6—C5—H5	120.4	O4—C20—H20A	109.5
C4—C5—H5	120.4	O4—C20—H20B	109.5
N1—C6—C5	121.6 (2)	H20A—C20—H20B	109.5
N1—C6—H6	119.2	O4—C20—H20C	109.5
C5—C6—H6	119.2	H20A—C20—H20C	109.5
N2—C7—C8	120.1 (3)	H20B—C20—H20C	109.5
N2—C7—H7	119.9
N1—Sn1—O1—C1	−2.17 (18)	N2—C7—C8—C9	−0.6 (4)
Cl3—Sn1—O1—C1	−94.42 (18)	C7—C8—C9—C10	0.1 (4)
Cl2—Sn1—O1—C1	−1.2 (4)	C8—C9—C10—C19	0.7 (4)
Cl1—Sn1—O1—C1	172.13 (18)	C8—C9—C10—C11	−178.4 (2)
Cl4—Sn1—O1—C1	82.12 (18)	C9—C10—C11—C12	179.8 (2)
O1—Sn1—N1—C6	177.6 (2)	C19—C10—C11—C12	0.7 (4)
Cl3—Sn1—N1—C6	−95.0 (2)	C10—C11—C12—C13	0.5 (4)
Cl2—Sn1—N1—C6	−2.2 (2)	C11—C12—C13—C14	179.7 (3)
Cl1—Sn1—N1—C6	147.4 (2)	C11—C12—C13—C18	−1.1 (4)
Cl4—Sn1—N1—C6	89.0 (2)	C18—C13—C14—C15	0.2 (4)
O1—Sn1—N1—C2	4.76 (17)	C12—C13—C14—C15	179.4 (3)
Cl3—Sn1—N1—C2	92.16 (17)	C13—C14—C15—C16	0.1 (4)
Cl2—Sn1—N1—C2	−175.07 (17)	C14—C15—C16—C17	0.1 (4)
Cl1—Sn1—N1—C2	−25.5 (4)	C15—C16—C17—O3	178.8 (2)
Cl4—Sn1—N1—C2	−83.84 (17)	C15—C16—C17—C18	−0.6 (4)
Sn1—O1—C1—O2	−179.9 (2)	O3—C17—C18—C13	−178.5 (2)
Sn1—O1—C1—C2	−0.6 (3)	C16—C17—C18—C13	0.9 (4)
C6—N1—C2—C3	0.0 (4)	O3—C17—C18—C19	1.1 (4)
Sn1—N1—C2—C3	173.5 (2)	C16—C17—C18—C19	−179.4 (2)
C6—N1—C2—C1	180.0 (2)	C14—C13—C18—C17	−0.7 (4)
Sn1—N1—C2—C1	−6.5 (3)	C12—C13—C18—C17	−179.9 (2)
O2—C1—C2—N1	−175.7 (2)	C14—C13—C18—C19	179.6 (2)
O1—C1—C2—N1	4.9 (3)	C12—C13—C18—C19	0.4 (4)
O2—C1—C2—C3	4.3 (4)	C7—N2—C19—C10	0.5 (4)
O1—C1—C2—C3	−175.1 (3)	C7—N2—C19—C18	−179.9 (2)
N1—C2—C3—C4	0.0 (4)	C9—C10—C19—N2	−1.0 (3)
C1—C2—C3—C4	−180.0 (2)	C11—C10—C19—N2	178.1 (2)
C2—C3—C4—C5	0.4 (4)	C9—C10—C19—C18	179.5 (2)
C3—C4—C5—C6	−0.7 (4)	C11—C10—C19—C18	−1.4 (4)
C2—N1—C6—C5	−0.4 (4)	C17—C18—C19—N2	1.7 (4)
Sn1—N1—C6—C5	−172.9 (2)	C13—C18—C19—N2	−178.7 (2)
C4—C5—C6—N1	0.8 (5)	C17—C18—C19—C10	−178.8 (2)
C19—N2—C7—C8	0.3 (4)	C13—C18—C19—C10	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.84 (1)	1.73 (1)	2.554 (2)	170 (3)
O4—H4···O2	0.83 (1)	1.87 (1)	2.698 (3)	174 (3)
N2—H2···Cl4i	0.87 (1)	2.58 (2)	3.255 (2)	135 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.84 (1)	1.73 (1)	2.554 (2)	170 (3)
O4—H4⋯O2	0.83 (1)	1.87 (1)	2.698 (3)	174 (3)
N2—H2⋯Cl4i	0.87 (1)	2.58 (2)	3.255 (2)	135 (2)

Symmetry code: (i) .