8-Hy­droxy-2-methyl­quinolinium tetra­chlorido(quinolin-2-olato-κ2N,O)stannate(IV) methanol disolvate

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536811001954

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m241

doi:10.1107/S1600536811001954

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8-Hydroxy-2-methylquinolinium tetrachlorido(quinolin-2-olato-κ²N,O)stannate(IV) methanol disolvate

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 8 January 2011; accepted 12 January 2011; online 22 January 2011)

In the reaction of 8-hydroxyquinoline, 2-methyl-8-hydroxyquinoline and stannic chloride, the 2-methyl-8-hydroxyquinoline is protonated, yielding the disolvated title salt, (C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]·2CH₃OH. The Sn^IV atom in the anion is N,O-chelated by the hydroxyquinolinate in a cis-SnNOCl₄ octahedral geometry. In the crystal, the cation, anion and solvent molecules 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_r = 628.91
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.049
wR(F²) = 0.130
S = 1.05
5371 reflections
295 parameters
H-atom parameters constrained
Δρ_max = 1.76 e Å⁻³
Δρ_min = −1.85 e Å⁻³

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) x+1, y+1, z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Only symmetrical dichlorotin bis(oxinates) have been reported; these include the 8-hydroxyquinoline, 2-methyl-8-hydroxyquinoline and 5,7-dichloro-8-hydroxyquinoline derivatives (Archer et al., 1987; Fazaeli et al., 2009; Lo & Ng, 2009). In the reaction of 8-hydroxyquinoline, 2-methyl-8-hydroxyquinoline and stannic chloride, the 2-methyl-8-hydroxyquinoline is protonated to yield the disolvated salt, [SnCl₄(C₉H₆NO₂)]^-.2CH₃OH (Scheme I, Fig. 1). The tin atom in the anion is N,O-chelated by the hydroxyquinolinate and it exists in a cis-SnNOCl₄ octahedral geometry. The cation, anion and solvent molecules are linked by N–H···O and O–H···O hydrogen bonds to generate a three-dimensional network (Table 1).

Related literature top

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

Experimental top

Stannic chloride pentahydrate (0.35 g, 1 mmol), 8-hydroxyquinoline (0.15 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.16 g, 1 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Yellow crystals were collected from the side arm after several days.

Computing details top

Data collection: CrysAlis PRO (Agilent Technologies, 2010); cell refinement: CrysAlis PRO (Agilent Technologies, 2010); data reduction: CrysAlis PRO (Agilent Technologies, 2010); 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).

Figures top

Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [C₁₀H₁₀NO]⁺ [SnCl₄(C₉H₆NO)]^–. 2CH₃OH at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

8-Hydroxy-2-methylquinolinium tetrachlorido(quinolin-2-olato-κ²N,O)stannate(IV) methanol disolvate top

Crystal data top

(C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]·2CH₄O	Z = 2
M_r = 628.91	F(000) = 628
Triclinic, P1	D_x = 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

Data collection top

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 monochromator	R_int = 0.040
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	k = −11→12
T_min = 0.659, T_max = 0.751	l = −16→20
8825 measured reflections

Refinement top

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(F_o²) + (0.0633P)²] where P = (F_o² + 2F_c²)/3
5371 reflections	(Δ/σ)_max = 0.001
295 parameters	Δρ_max = 1.76 e Å⁻³
0 restraints	Δρ_min = −1.85 e Å⁻³

Crystal data top

(C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]·2CH₄O	γ = 88.529 (3)°
M_r = 628.91	V = 1217.53 (9) Å³
Triclinic, P1	Z = 2
a = 7.9395 (3) Å	Mo Kα radiation
b = 9.9721 (4) Å	µ = 1.52 mm⁻¹
c = 16.0531 (8) Å	T = 100 K
α = 75.056 (4)°	0.30 × 0.25 × 0.20 mm
β = 82.529 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	5371 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent Technologies, 2010)	4258 reflections with I > 2σ(I)
T_min = 0.659, T_max = 0.751	R_int = 0.040
8825 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.05	Δρ_max = 1.76 e Å⁻³
5371 reflections	Δρ_min = −1.85 e Å⁻³
295 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]·2CH₄O
M_r	628.91
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	7.9395 (3), 9.9721 (4), 16.0531 (8)
α, β, γ (°)	75.056 (4), 82.529 (4), 88.529 (3)
V (Å³)	1217.53 (9)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.52
Crystal size (mm)	0.30 × 0.25 × 0.20

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent Technologies, 2010)
T_min, T_max	0.659, 0.751
No. of measured, independent and observed [I > 2σ(I)] reflections	8825, 5371, 4258
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.130, 1.05
No. of reflections	5371
No. of parameters	295
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.76, −1.85

Computer programs: CrysAlis PRO (Agilent Technologies, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x+1, y+1, z.

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

Agilent Technologies (2010). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
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