8-Hydr­oxy-2-methyl­quinolinium tetra­chlorido(quinolin-8-olato-κ2N,O)stannate(IV) acetonitrile monosolvate

Vafaee, M.; Mohammadnezhad, G.; Amini, M.M.; Ng, S.W.

doi:10.1107/S160053681000810X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Pages m381-m382

doi:10.1107/S160053681000810X

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8-Hydroxy-2-methylquinolinium tetrachlorido(quinolin-8-olato-κ²N,O)stannate(IV) acetonitrile monosolvate

Marzieh Vafaee,^a Gholamhossein Mohammadnezhad,^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 1 March 2010; accepted 2 March 2010; online 6 March 2010)

In the title solvated salt, (C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]·CH₃CN, the Sn^IV atom is chelated by the N,O-bidentate 8-hydroxyquinolinate ligand and four chloride ions, generating a distorted SnONCl₄ octahedral coordination geometry for the metal. In the crystal, the cations are linked to the anions and the solvent molecules by O—H⋯O and N—H⋯N hydrogen bonds, respectively.

Related literature

For the spectroscopic characterization of the tetrachlorido(quinolinato)stannate(IV) anion in other salts, see: Cunningham et al. (1977 ); Douek et al. (1967 ); Frazer & Goffer (1996 ); Frazer & Rimmer (1968 ); Greenwood & Ruddick (1967 ). For the structures of dichloridobis(quinolin-8-olato)tin and dichloridobis(2-methylquinolin-8-olato)tin, see: Archer et al. (1987 ); Lo & Ng (2009 ). For a related structure, see: Mohammadnezhad et al. (2010 ).

Experimental

Crystal data

(C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]·C₂H₃N
M_r = 605.88
Monoclinic, C 2/c
a = 29.1672 (14) Å
b = 10.9415 (5) Å
c = 15.4907 (8) Å
β = 99.9411 (6)°
V = 4869.4 (4) Å³
Z = 8
Mo Kα radiation
μ = 1.51 mm⁻¹
T = 296 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.583, T_max = 0.752
22804 measured reflections
5594 independent reflections
4663 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.023
wR(F²) = 0.064
S = 1.02
5594 reflections
290 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Sn1—N1	2.203 (2)
Sn1—O1	2.077 (1)
Sn1—Cl1	2.3741 (6)
Sn1—Cl2	2.4055 (6)
Sn1—Cl3	2.4130 (6)
Sn1—Cl4	2.4176 (6)

O1—Sn1—N1	78.08 (6)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯O1	0.85 (1)	1.91 (2)	2.715 (2)	158 (3)
N2—H2n⋯N3	0.85 (1)	2.15 (1)	2.972 (3)	162 (2)

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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/S160053681000810X/hb5348sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681000810X/hb5348Isup2.hkl

checkCIF report

Comment top

The 8-hydroxyquinoline anion furnishes a number of compounds with both inorganic tin(IV) and organotin(IV) systems; for example, the crystal structure of dichlorobis(quinolin-8-olato)tin has been known some time back (Archer et al., 1987). The presence of a methyl substituent in the 2-position introduces steric problems (Mohammadnezhad et al., 2010); this may affect the ability of the complexes to crystallize well so that fewer such complexes have been reported. The crystal structure of dichlorobis(2-methylquinolin-8-olato)tin has only recently been reported (Lo & Ng, 2009). On the other hand, mixed chelate complexes are difficult to synthesize as the compounds disproportionate into the symmetrical derivatives.

The reaction of tin(IV) chloride with 8-hydroxyquinoline and 2-methyl-8-hydroxyquinoline in acetonitrile yields instead the salt, 8-hydroxy-2-methylquinolinium tetrachloro(quinolin-8-olato)stannate as the acetonitrile solvate (Scheme I, Fig. 1). Owing to the steric bulk of the methyl group, the 2-methy-8-hydroxyquinoline component does not engage in binding to the tin atom but merely functions as a proton abstractor. In the salt, the tin atom is chelated by the 8-hydroxyquinolinato unit and it exists in an octahedral coordination geometry. The tin-chlorine bonds trans to the chelating atoms are significantly shorter than the other tin-chlorine bonds (Table 1). The cation is linked to the anion by an O–H···O hydrogen bond; the cation is linked to solvent molecule by an N–H···N hydrogen bond (Table 2). The stannate has been spectroscopically characterized in other salts (Cunningham et al., 1977; Douek et al., 1967; Frazer & Goffer, 1996; Frazer & Rimmer, 1968; Greenwood & Ruddick, 1967).

Related literature top

For the spectroscopic characterization of the tetrachlorido(quinolinato)stannate(IV) anion in other salts, see: Cunningham et al. (1977); Douek et al. (1967); Frazer & Goffer (1996); Frazer & Rimmer (1968); Greenwood & Ruddick (1967). For the structures of dichlorobis(quinolin-8-olato)tin and dichloridobis(2-methylquinolin-8-olato)tin, see: Archer et al. (1987); Lo & Ng (2009). For a related structure, see: Mohammadnezhad et al. (2010).

Experimental top

Stannic chloride pentahydrate(1 mmol, 0.35 g), 8-hydroxyquinoline (1 mmol, 0.15 g) and 2-methyl-8-hydroxyquinoline (1 mmol, 0.16 g) were placed in a convection tube; the tube was filled with acetonitrile and kept at 333 K. Yellow prisms of (I) were collected after a week.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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. The molecular structure of (I): displacement ellipsoids are drawn at the 50% probability level and H atoms are of arbitrary radius.

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

Crystal data top

(C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]·C₂H₃N	F(000) = 2400
M_r = 605.88	D_x = 1.653 Mg m⁻³
Monoclinic, C2/c	Melting point: 408 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 29.1672 (14) Å	Cell parameters from 9937 reflections
b = 10.9415 (5) Å	θ = 2.3–28.3°
c = 15.4907 (8) Å	µ = 1.51 mm⁻¹
β = 99.9411 (6)°	T = 296 K
V = 4869.4 (4) Å³	Prism, yellow
Z = 8	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART APEX diffractometer	5594 independent reflections
Radiation source: fine-focus sealed tube	4663 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −37→37
T_min = 0.583, T_max = 0.752	k = −14→14
22804 measured reflections	l = −20→20

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)] = 0.023	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0319P)² + 3.2971P] where P = (F_o² + 2F_c²)/3
5594 reflections	(Δ/σ)_max = 0.001
290 parameters	Δρ_max = 0.28 e Å⁻³
2 restraints	Δρ_min = −0.54 e Å⁻³

Crystal data top

(C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]·C₂H₃N	V = 4869.4 (4) Å³
M_r = 605.88	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.1672 (14) Å	µ = 1.51 mm⁻¹
b = 10.9415 (5) Å	T = 296 K
c = 15.4907 (8) Å	0.40 × 0.30 × 0.20 mm
β = 99.9411 (6)°

Data collection top

Bruker SMART APEX diffractometer	5594 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4663 reflections with I > 2σ(I)
T_min = 0.583, T_max = 0.752	R_int = 0.027
22804 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.023	2 restraints
wR(F²) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.28 e Å⁻³
5594 reflections	Δρ_min = −0.54 e Å⁻³
290 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.395979 (5)	0.698425 (12)	0.408891 (9)	0.03485 (6)
Cl1	0.37060 (2)	0.76784 (6)	0.53800 (4)	0.05477 (15)
Cl2	0.40349 (2)	0.89500 (5)	0.34322 (5)	0.06272 (18)
Cl3	0.476603 (19)	0.70536 (6)	0.47849 (4)	0.04984 (14)
Cl4	0.31714 (2)	0.68113 (6)	0.33007 (4)	0.05257 (15)
O1	0.39266 (5)	0.51704 (12)	0.44682 (9)	0.0390 (3)
O2	0.34376 (6)	0.38174 (17)	0.54651 (13)	0.0573 (5)
H2O	0.3527 (11)	0.436 (2)	0.5137 (19)	0.092 (12)*
N1	0.41915 (6)	0.60155 (16)	0.29942 (11)	0.0395 (4)
N2	0.29662 (7)	0.20670 (18)	0.61441 (12)	0.0443 (4)
H2N	0.3234 (5)	0.197 (2)	0.6006 (16)	0.044 (7)*
N3	0.38826 (10)	0.1151 (2)	0.58312 (19)	0.0753 (7)
C1	0.43162 (9)	0.6467 (3)	0.22790 (15)	0.0533 (6)
H1	0.4306	0.7308	0.2191	0.064*
C2	0.44621 (9)	0.5712 (3)	0.16521 (16)	0.0621 (7)
H2	0.4549	0.6050	0.1154	0.075*
C3	0.44759 (9)	0.4489 (3)	0.17715 (16)	0.0614 (7)
H3	0.4571	0.3987	0.1351	0.074*
C4	0.43490 (8)	0.3968 (2)	0.25239 (15)	0.0488 (6)
C5	0.43577 (10)	0.2710 (3)	0.2723 (2)	0.0648 (8)
H5	0.4447	0.2149	0.2332	0.078*
C6	0.42365 (10)	0.2317 (2)	0.3480 (2)	0.0618 (7)
H6	0.4248	0.1484	0.3603	0.074*
C7	0.40938 (8)	0.31228 (19)	0.40858 (17)	0.0453 (5)
H7	0.4015	0.2821	0.4602	0.054*
C8	0.40704 (7)	0.43536 (18)	0.39199 (14)	0.0358 (4)
C9	0.42052 (7)	0.47834 (19)	0.31345 (13)	0.0364 (4)
C10	0.30128 (11)	−0.0040 (3)	0.6638 (2)	0.0714 (8)
H10A	0.3128	−0.0270	0.6117	0.107*
H10B	0.2803	−0.0657	0.6777	0.107*
H10C	0.3269	0.0042	0.7116	0.107*
C11	0.27629 (9)	0.1142 (2)	0.64902 (15)	0.0547 (6)
C12	0.23234 (10)	0.1348 (3)	0.67019 (19)	0.0693 (8)
H12	0.2173	0.0719	0.6946	0.083*
C13	0.21137 (9)	0.2439 (3)	0.65597 (19)	0.0687 (8)
H13	0.1821	0.2549	0.6707	0.082*
C14	0.23274 (8)	0.3424 (3)	0.61921 (15)	0.0530 (6)
C15	0.21283 (10)	0.4587 (3)	0.6017 (2)	0.0702 (8)
H15	0.1831	0.4746	0.6129	0.084*
C16	0.23708 (11)	0.5477 (3)	0.5685 (2)	0.0718 (8)
H16	0.2240	0.6251	0.5588	0.086*
C17	0.28137 (10)	0.5257 (3)	0.54830 (18)	0.0617 (7)
H17	0.2971	0.5879	0.5247	0.074*
C18	0.30146 (8)	0.4131 (2)	0.56320 (15)	0.0456 (5)
C19	0.27715 (8)	0.3204 (2)	0.59882 (14)	0.0431 (5)
C20	0.42250 (11)	0.0664 (2)	0.58977 (18)	0.0582 (7)
C21	0.46668 (12)	0.0043 (3)	0.5990 (3)	0.0996 (13)
H21A	0.4639	−0.0652	0.5606	0.149*
H21B	0.4758	−0.0224	0.6585	0.149*
H21C	0.4898	0.0592	0.5840	0.149*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03691 (9)	0.02715 (8)	0.04003 (8)	0.00082 (5)	0.00535 (6)	0.00091 (5)
Cl1	0.0529 (3)	0.0571 (4)	0.0555 (3)	0.0079 (3)	0.0127 (3)	−0.0166 (3)
Cl2	0.0668 (4)	0.0322 (3)	0.0873 (5)	−0.0024 (3)	0.0084 (3)	0.0155 (3)
Cl3	0.0356 (3)	0.0614 (4)	0.0513 (3)	0.0017 (2)	0.0039 (2)	−0.0024 (3)
Cl4	0.0404 (3)	0.0569 (4)	0.0562 (3)	−0.0032 (2)	−0.0035 (2)	0.0031 (3)
O1	0.0508 (9)	0.0289 (7)	0.0405 (8)	0.0029 (6)	0.0172 (6)	0.0023 (6)
O2	0.0440 (9)	0.0543 (11)	0.0803 (13)	0.0083 (8)	0.0295 (9)	0.0185 (9)
N1	0.0414 (10)	0.0411 (10)	0.0362 (9)	−0.0020 (8)	0.0074 (7)	0.0025 (7)
N2	0.0389 (10)	0.0557 (12)	0.0395 (9)	−0.0072 (9)	0.0099 (8)	−0.0046 (8)
N3	0.0781 (18)	0.0534 (14)	0.099 (2)	0.0056 (13)	0.0267 (15)	0.0007 (13)
C1	0.0574 (15)	0.0613 (16)	0.0421 (12)	−0.0056 (12)	0.0111 (11)	0.0116 (11)
C2	0.0541 (15)	0.099 (2)	0.0353 (12)	−0.0032 (15)	0.0130 (11)	0.0036 (13)
C3	0.0488 (14)	0.095 (2)	0.0413 (13)	0.0014 (14)	0.0098 (11)	−0.0218 (14)
C4	0.0411 (12)	0.0569 (15)	0.0481 (13)	0.0005 (11)	0.0069 (10)	−0.0171 (11)
C5	0.0618 (17)	0.0542 (16)	0.0785 (19)	0.0066 (13)	0.0119 (14)	−0.0315 (14)
C6	0.0592 (16)	0.0318 (12)	0.093 (2)	0.0027 (11)	0.0107 (15)	−0.0111 (13)
C7	0.0413 (12)	0.0335 (11)	0.0608 (14)	0.0005 (9)	0.0079 (10)	0.0024 (10)
C8	0.0314 (10)	0.0326 (10)	0.0429 (11)	0.0017 (8)	0.0049 (8)	−0.0023 (8)
C9	0.0305 (10)	0.0399 (11)	0.0382 (10)	−0.0002 (8)	0.0038 (8)	−0.0053 (8)
C10	0.084 (2)	0.0607 (18)	0.0682 (18)	−0.0182 (16)	0.0103 (15)	0.0090 (14)
C11	0.0583 (15)	0.0628 (16)	0.0432 (12)	−0.0222 (13)	0.0089 (11)	−0.0087 (11)
C12	0.0610 (17)	0.087 (2)	0.0643 (17)	−0.0347 (17)	0.0225 (14)	−0.0148 (16)
C13	0.0393 (14)	0.105 (2)	0.0656 (17)	−0.0219 (16)	0.0196 (12)	−0.0243 (17)
C14	0.0364 (12)	0.0810 (18)	0.0420 (12)	−0.0035 (12)	0.0073 (10)	−0.0158 (12)
C15	0.0425 (14)	0.103 (2)	0.0658 (17)	0.0164 (16)	0.0119 (13)	−0.0178 (17)
C16	0.0644 (18)	0.079 (2)	0.0728 (19)	0.0302 (16)	0.0144 (15)	−0.0023 (16)
C17	0.0585 (16)	0.0626 (17)	0.0656 (17)	0.0112 (13)	0.0152 (13)	0.0048 (13)
C18	0.0381 (11)	0.0555 (14)	0.0443 (12)	0.0036 (10)	0.0102 (9)	−0.0019 (10)
C19	0.0350 (11)	0.0592 (14)	0.0345 (10)	−0.0042 (10)	0.0044 (9)	−0.0085 (9)
C20	0.0721 (19)	0.0400 (13)	0.0665 (17)	−0.0085 (13)	0.0229 (14)	−0.0031 (12)
C21	0.068 (2)	0.070 (2)	0.167 (4)	−0.0003 (17)	0.036 (2)	−0.001 (2)

Geometric parameters (Å, º) top

Sn1—N1	2.203 (2)	C6—H6	0.9300
Sn1—O1	2.077 (1)	C7—C8	1.371 (3)
Sn1—Cl1	2.3741 (6)	C7—H7	0.9300
Sn1—Cl2	2.4055 (6)	C8—C9	1.422 (3)
Sn1—Cl3	2.4130 (6)	C10—C11	1.482 (4)
Sn1—Cl4	2.4176 (6)	C10—H10A	0.9600
O1—C8	1.349 (2)	C10—H10B	0.9600
O2—C18	1.348 (3)	C10—H10C	0.9600
O2—H2O	0.849 (10)	C11—C12	1.395 (4)
N1—C1	1.320 (3)	C12—C13	1.341 (5)
N1—C9	1.365 (3)	C12—H12	0.9300
N2—C11	1.332 (3)	C13—C14	1.413 (4)
N2—C19	1.371 (3)	C13—H13	0.9300
N2—H2N	0.852 (10)	C14—C19	1.406 (3)
N3—C20	1.121 (4)	C14—C15	1.406 (4)
C1—C2	1.396 (4)	C15—C16	1.356 (4)
C1—H1	0.9300	C15—H15	0.9300
C2—C3	1.351 (4)	C16—C17	1.401 (4)
C2—H2	0.9300	C16—H16	0.9300
C3—C4	1.403 (4)	C17—C18	1.367 (3)
C3—H3	0.9300	C17—H17	0.9300
C4—C5	1.410 (4)	C18—C19	1.404 (3)
C4—C9	1.415 (3)	C20—C21	1.442 (4)
C5—C6	1.352 (4)	C21—H21A	0.9600
C5—H5	0.9300	C21—H21B	0.9600
C6—C7	1.402 (4)	C21—H21C	0.9600

O1—Sn1—N1	78.08 (6)	O1—C8—C9	118.80 (18)
O1—Sn1—Cl1	91.77 (4)	C7—C8—C9	118.2 (2)
N1—Sn1—Cl1	169.83 (5)	N1—C9—C4	121.3 (2)
O1—Sn1—Cl2	170.48 (4)	N1—C9—C8	117.27 (18)
N1—Sn1—Cl2	92.42 (5)	C4—C9—C8	121.4 (2)
Cl1—Sn1—Cl2	97.74 (3)	C11—C10—H10A	109.5
O1—Sn1—Cl3	89.60 (4)	C11—C10—H10B	109.5
N1—Sn1—Cl3	87.37 (5)	H10A—C10—H10B	109.5
Cl1—Sn1—Cl3	92.01 (2)	C11—C10—H10C	109.5
Cl2—Sn1—Cl3	90.45 (2)	H10A—C10—H10C	109.5
O1—Sn1—Cl4	88.93 (4)	H10B—C10—H10C	109.5
N1—Sn1—Cl4	88.00 (5)	N2—C11—C12	117.6 (3)
Cl1—Sn1—Cl4	92.45 (2)	N2—C11—C10	118.9 (2)
Cl2—Sn1—Cl4	90.26 (2)	C12—C11—C10	123.5 (3)
Cl3—Sn1—Cl4	175.34 (2)	C13—C12—C11	121.1 (3)
C8—O1—Sn1	114.85 (12)	C13—C12—H12	119.4
C18—O2—H2O	109 (2)	C11—C12—H12	119.4
C1—N1—C9	119.9 (2)	C12—C13—C14	121.6 (3)
C1—N1—Sn1	129.17 (17)	C12—C13—H13	119.2
C9—N1—Sn1	110.92 (13)	C14—C13—H13	119.2
C11—N2—C19	124.1 (2)	C19—C14—C15	118.5 (3)
C11—N2—H2N	119.6 (16)	C19—C14—C13	116.6 (3)
C19—N2—H2N	116.3 (16)	C15—C14—C13	124.9 (3)
N1—C1—C2	121.6 (3)	C16—C15—C14	119.9 (3)
N1—C1—H1	119.2	C16—C15—H15	120.1
C2—C1—H1	119.2	C14—C15—H15	120.1
C3—C2—C1	119.8 (2)	C15—C16—C17	121.5 (3)
C3—C2—H2	120.1	C15—C16—H16	119.2
C1—C2—H2	120.1	C17—C16—H16	119.2
C2—C3—C4	120.7 (2)	C18—C17—C16	120.1 (3)
C2—C3—H3	119.7	C18—C17—H17	119.9
C4—C3—H3	119.7	C16—C17—H17	119.9
C3—C4—C5	125.5 (2)	O2—C18—C17	125.2 (2)
C3—C4—C9	116.8 (2)	O2—C18—C19	115.6 (2)
C5—C4—C9	117.7 (2)	C17—C18—C19	119.1 (2)
C6—C5—C4	120.2 (2)	N2—C19—C18	120.2 (2)
C6—C5—H5	119.9	N2—C19—C14	119.0 (2)
C4—C5—H5	119.9	C18—C19—C14	120.8 (2)
C5—C6—C7	122.2 (2)	N3—C20—C21	179.5 (4)
C5—C6—H6	118.9	C20—C21—H21A	109.5
C7—C6—H6	118.9	C20—C21—H21B	109.5
C8—C7—C6	120.2 (2)	H21A—C21—H21B	109.5
C8—C7—H7	119.9	C20—C21—H21C	109.5
C6—C7—H7	119.9	H21A—C21—H21C	109.5
O1—C8—C7	122.9 (2)	H21B—C21—H21C	109.5

N1—Sn1—O1—C8	2.45 (13)	C3—C4—C9—N1	0.0 (3)
Cl1—Sn1—O1—C8	−176.95 (13)	C5—C4—C9—N1	179.4 (2)
Cl3—Sn1—O1—C8	−84.95 (13)	C3—C4—C9—C8	−179.8 (2)
Cl4—Sn1—O1—C8	90.63 (13)	C5—C4—C9—C8	−0.5 (3)
O1—Sn1—N1—C1	179.6 (2)	O1—C8—C9—N1	1.6 (3)
Cl1—Sn1—N1—C1	−177.0 (2)	C7—C8—C9—N1	−178.21 (19)
Cl2—Sn1—N1—C1	0.1 (2)	O1—C8—C9—C4	−178.54 (18)
Cl3—Sn1—N1—C1	−90.3 (2)	C7—C8—C9—C4	1.6 (3)
Cl4—Sn1—N1—C1	90.2 (2)	C19—N2—C11—C12	0.3 (3)
O1—Sn1—N1—C9	−1.57 (13)	C19—N2—C11—C10	−179.2 (2)
Cl1—Sn1—N1—C9	1.8 (4)	N2—C11—C12—C13	0.1 (4)
Cl2—Sn1—N1—C9	178.93 (13)	C10—C11—C12—C13	179.6 (3)
Cl3—Sn1—N1—C9	88.58 (13)	C11—C12—C13—C14	−0.1 (4)
Cl4—Sn1—N1—C9	−90.90 (13)	C12—C13—C14—C19	−0.3 (4)
C9—N1—C1—C2	0.2 (3)	C12—C13—C14—C15	179.4 (3)
Sn1—N1—C1—C2	178.98 (17)	C19—C14—C15—C16	−2.0 (4)
N1—C1—C2—C3	0.2 (4)	C13—C14—C15—C16	178.2 (3)
C1—C2—C3—C4	−0.6 (4)	C14—C15—C16—C17	2.0 (5)
C2—C3—C4—C5	−178.9 (3)	C15—C16—C17—C18	−1.0 (5)
C2—C3—C4—C9	0.5 (4)	C16—C17—C18—O2	−179.9 (3)
C3—C4—C5—C6	178.6 (3)	C16—C17—C18—C19	0.0 (4)
C9—C4—C5—C6	−0.7 (4)	C11—N2—C19—C18	179.1 (2)
C4—C5—C6—C7	0.8 (4)	C11—N2—C19—C14	−0.8 (3)
C5—C6—C7—C8	0.4 (4)	O2—C18—C19—N2	0.0 (3)
Sn1—O1—C8—C7	176.79 (17)	C17—C18—C19—N2	−179.9 (2)
Sn1—O1—C8—C9	−3.1 (2)	O2—C18—C19—C14	179.8 (2)
C6—C7—C8—O1	178.6 (2)	C17—C18—C19—C14	−0.1 (3)
C6—C7—C8—C9	−1.6 (3)	C15—C14—C19—N2	−179.1 (2)
C1—N1—C9—C4	−0.3 (3)	C13—C14—C19—N2	0.7 (3)
Sn1—N1—C9—C4	−179.30 (16)	C15—C14—C19—C18	1.1 (3)
C1—N1—C9—C8	179.5 (2)	C13—C14—C19—C18	−179.1 (2)
Sn1—N1—C9—C8	0.5 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1	0.85 (1)	1.91 (2)	2.715 (2)	158 (3)
N2—H2n···N3	0.85 (1)	2.15 (1)	2.972 (3)	162 (2)

Experimental details

Crystal data
Chemical formula	(C₁₀H₁₀NO)[SnCl₄(C₉H₆NO)]·C₂H₃N
M_r	605.88
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	29.1672 (14), 10.9415 (5), 15.4907 (8)
β (°)	99.9411 (6)
V (Å³)	4869.4 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.51
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.583, 0.752
No. of measured, independent and observed [I > 2σ(I)] reflections	22804, 5594, 4663
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.023, 0.064, 1.02
No. of reflections	5594
No. of parameters	290
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.54

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Sn1—N1	2.203 (2)	Sn1—Cl2	2.4055 (6)
Sn1—O1	2.077 (1)	Sn1—Cl3	2.4130 (6)
Sn1—Cl1	2.3741 (6)	Sn1—Cl4	2.4176 (6)

O1—Sn1—N1	78.08 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O1	0.85 (1)	1.91 (2)	2.715 (2)	158 (3)
N2—H2n···N3	0.85 (1)	2.15 (1)	2.972 (3)	162 (2)

Acknowledgements

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

References

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