2-(Methoxy­carbon­yl)quinolinium tetra­chlorido(quinoline-2-carboxyl­ato-κ2N,O)stannate(IV) methanol solvate

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

doi:10.1107/S1600536810008561

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 4| April 2010| Page m390

doi:10.1107/S1600536810008561

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2-(Methoxycarbonyl)quinolinium tetrachlorido(quinoline-2-carboxylato-κ²N,O)stannate(IV) methanol solvate

Marzieh Vafaee,^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 4 March 2010; accepted 5 March 2010; online 10 March 2010)

In the title salt, (C₁₁H₁₀NO₂)[SnCl₄(C₁₀H₆NO₂)]·CH₃OH, the Sn atom is chelated by the quinolincarboxylate unit and it exists in a distorted octahedral coordination geometry. The cation is linked to the solvent molecule by an N—H⋯O hydrogen bond; the solvent molecule is linked to the anion by an O—H⋯O hydrogen bond.

Related literature

For the structure of 2-(ethoxycarbonyl)quinolinium n-butyltrichlorido(quinolin-2-carboxylato)stannate(IV), see: Wang et al. (2008 ).

Experimental

Crystal data

(C₁₁H₁₀NO₂)[SnCl₄(C₁₀H₆NO₂)]·CH₄O
M_r = 652.89
Monoclinic, P 2₁ /n
a = 8.4109 (4) Å
b = 33.2728 (16) Å
c = 10.0241 (5) Å
β = 112.8616 (6)°
V = 2584.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 1.44 mm⁻¹
T = 293 K
0.35 × 0.25 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.633, T_max = 0.813
24727 measured reflections
5924 independent reflections
5288 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.104
S = 1.17
5924 reflections
317 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −1.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2	0.84 (1)	1.95 (1)	2.785 (4)	176 (5)
N3—H3⋯O5	0.86 (1)	1.85 (2)	2.693 (4)	166 (4)

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/S1600536810008561/bt5208sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810008561/bt5208Isup2.hkl

checkCIF report

Comment top

Quinolin-2-carboxylic acid forms a number of compounds with organotin(IV) systems in which the deprotonated anion N,O-chelates to the tin atom. Such organotin carboxylates are conveniently synthesized by the reaction of an organotin chloride with the sodium salt of the carboxylic acid. Curiously, the reaction of sodium quinolin-2-carboxylate with n-butyltin trichloride furnishes the n-butyltrichlorido(quinolincarboxylato)stannate anion, whose charge is balanced by an ethyl quinoliniumcarboxylate cation (Wang et al., 2008). The ethyl unit arises from the ethanol solvent used in the synthesis.

In our hands, the reaction of quinolin-2-carboxylic acid with stannic chloride has yielded a similar salt, which crystallizes as a methanol solvate (Scheme I, Fig. 1). The solvent is also involved in the esterification of the acid to furnish the cation. The cation is linked to the solvent molecule by an N–H···O hydrogen bond; the solvent molecule is linked to the anion by an O–H···O hydrogen bond.

Related literature top

For the structure of 2-(ethoxycarbonyl)quinolinium n-butyltrichlorido(quinolin-2-carboxylato)stannate, see: Wang et al. (2008).

Experimental top

Stannic chloride pentahydrate (1 mmol, 0.350 g) and quinaldic acid (2 mmol, 0.173 g) were dissolved in dry methanol. The solvent was allowed to evaporate to afford colorless crystals after 1 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. Anisotropic displacement ellipsoid plot (Barbour, 2001) of [C₁₁H₁₀NO₂][SnCl₄(C₁₀H₆NO₂)]^.CH₃OH; ellipsoids are drawn at the 50% probability level and H atoms are of arbitrary radius. Hydrogen bonds are drawn as dashed lines.

2-(Methoxycarbonyl)quinolinium tetrachlorido(quinoline-2-carboxylato-κ²N,O)stannate(IV) methanol solvate top

Crystal data top

(C₁₁H₁₀NO₂)[SnCl₄(C₁₀H₆NO₂)]·CH₄O	F(000) = 1296
M_r = 652.89	D_x = 1.678 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9921 reflections
a = 8.4109 (4) Å	θ = 2.3–28.1°
b = 33.2728 (16) Å	µ = 1.44 mm⁻¹
c = 10.0241 (5) Å	T = 293 K
β = 112.8616 (6)°	Wedge, colorless
V = 2584.9 (2) Å³	0.35 × 0.25 × 0.15 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5924 independent reflections
Radiation source: fine-focus sealed tube	5288 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ω scans	θ_max = 27.5°, θ_min = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.633, T_max = 0.813	k = −43→42
24727 measured reflections	l = −13→13

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ²(F_o²) + (0.0423P)² + 3.5411P] where P = (F_o² + 2F_c²)/3
5924 reflections	(Δ/σ)_max = 0.001
317 parameters	Δρ_max = 0.38 e Å⁻³
2 restraints	Δρ_min = −1.15 e Å⁻³

Crystal data top

(C₁₁H₁₀NO₂)[SnCl₄(C₁₀H₆NO₂)]·CH₄O	V = 2584.9 (2) Å³
M_r = 652.89	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.4109 (4) Å	µ = 1.44 mm⁻¹
b = 33.2728 (16) Å	T = 293 K
c = 10.0241 (5) Å	0.35 × 0.25 × 0.15 mm
β = 112.8616 (6)°

Data collection top

Bruker SMART APEX diffractometer	5924 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5288 reflections with I > 2σ(I)
T_min = 0.633, T_max = 0.813	R_int = 0.026
24727 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	2 restraints
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	Δρ_max = 0.38 e Å⁻³
5924 reflections	Δρ_min = −1.15 e Å⁻³
317 parameters

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

	x	y	z	U_iso*/U_eq
Sn1	0.77625 (3)	0.625981 (7)	0.62161 (2)	0.03525 (9)
Cl1	0.79773 (15)	0.56055 (3)	0.53317 (11)	0.0513 (2)
Cl2	0.86453 (17)	0.60335 (4)	0.86654 (11)	0.0633 (3)
Cl3	1.06377 (14)	0.64544 (4)	0.66027 (14)	0.0661 (3)
Cl4	0.47849 (13)	0.61972 (3)	0.58488 (12)	0.0492 (2)
O1	0.6997 (4)	0.64512 (8)	0.4078 (3)	0.0419 (6)
O2	0.6522 (5)	0.69652 (10)	0.2599 (3)	0.0665 (9)
O3	0.1333 (4)	0.58105 (10)	0.2844 (4)	0.0573 (8)
O4	0.2708 (4)	0.62339 (9)	0.1913 (4)	0.0566 (8)
O5	0.5646 (4)	0.63000 (9)	0.0768 (3)	0.0476 (6)
N1	0.7356 (4)	0.69426 (9)	0.6318 (3)	0.0388 (7)
N3	0.4799 (4)	0.56215 (9)	0.1803 (3)	0.0376 (6)
C1	0.6875 (5)	0.68256 (12)	0.3810 (4)	0.0439 (9)
C2	0.7133 (5)	0.71104 (11)	0.5058 (4)	0.0408 (8)
C3	0.7086 (7)	0.75223 (13)	0.4836 (5)	0.0591 (12)
H3A	0.6919	0.7626	0.3930	0.071*
C4	0.7287 (7)	0.77719 (13)	0.5963 (5)	0.0638 (13)
H4	0.7297	0.8049	0.5840	0.077*
C5	0.7481 (6)	0.76113 (12)	0.7317 (5)	0.0505 (10)
C6	0.7654 (7)	0.78527 (14)	0.8525 (6)	0.0676 (14)
H6	0.7710	0.8131	0.8455	0.081*
C7	0.7741 (8)	0.76872 (16)	0.9772 (6)	0.0747 (16)
H7	0.7831	0.7851	1.0550	0.090*
C8	0.7696 (8)	0.72689 (16)	0.9909 (5)	0.0726 (15)
H8	0.7743	0.7157	1.0774	0.087*
C9	0.7581 (7)	0.70231 (14)	0.8775 (5)	0.0573 (12)
H9	0.7571	0.6746	0.8882	0.069*
C10	0.7480 (5)	0.71862 (11)	0.7467 (4)	0.0421 (8)
C11	0.2513 (5)	0.59121 (12)	0.2346 (4)	0.0423 (8)
C12	0.3641 (5)	0.55578 (11)	0.2379 (4)	0.0412 (8)
C13	0.3513 (6)	0.51870 (13)	0.2949 (5)	0.0530 (10)
H13	0.2686	0.5143	0.3337	0.064*
C14	0.4601 (7)	0.48872 (13)	0.2940 (5)	0.0599 (12)
H14	0.4528	0.4639	0.3339	0.072*
C15	0.5835 (6)	0.49474 (12)	0.2337 (4)	0.0503 (10)
C16	0.7009 (7)	0.46501 (15)	0.2295 (6)	0.0681 (14)
H16	0.7010	0.4399	0.2703	0.082*
C17	0.8142 (7)	0.47287 (17)	0.1659 (6)	0.0739 (16)
H17	0.8914	0.4531	0.1638	0.089*
C18	0.8150 (6)	0.51091 (17)	0.1030 (6)	0.0671 (14)
H18	0.8917	0.5156	0.0584	0.081*
C19	0.7058 (5)	0.54069 (14)	0.1064 (5)	0.0524 (10)
H19	0.7081	0.5656	0.0655	0.063*
C20	0.5903 (5)	0.53305 (11)	0.1727 (4)	0.0418 (8)
C21	0.0198 (7)	0.61294 (16)	0.2925 (7)	0.0707 (14)
H21A	−0.0661	0.6020	0.3231	0.106*
H21B	−0.0355	0.6251	0.1989	0.106*
H21C	0.0859	0.6328	0.3609	0.106*
C22	0.4323 (7)	0.64239 (17)	−0.0535 (5)	0.0680 (13)
H22A	0.3222	0.6360	−0.0511	0.102*
H22B	0.4445	0.6288	−0.1334	0.102*
H22C	0.4400	0.6709	−0.0649	0.102*
H3	0.490 (6)	0.5852 (7)	0.145 (4)	0.051 (13)*
H5	0.589 (7)	0.6495 (10)	0.135 (4)	0.069 (16)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.03944 (14)	0.03703 (14)	0.02901 (13)	0.00101 (10)	0.01300 (10)	0.00026 (9)
Cl1	0.0677 (7)	0.0394 (5)	0.0486 (5)	0.0063 (4)	0.0244 (5)	−0.0038 (4)
Cl2	0.0838 (8)	0.0711 (7)	0.0352 (5)	0.0275 (6)	0.0232 (5)	0.0130 (5)
Cl3	0.0402 (6)	0.0898 (9)	0.0675 (7)	−0.0076 (5)	0.0202 (5)	−0.0077 (6)
Cl4	0.0413 (5)	0.0480 (5)	0.0587 (6)	−0.0016 (4)	0.0200 (4)	0.0033 (4)
O1	0.0560 (16)	0.0409 (14)	0.0290 (12)	−0.0004 (12)	0.0168 (11)	−0.0010 (10)
O2	0.113 (3)	0.0531 (18)	0.0342 (15)	−0.0056 (18)	0.0291 (17)	0.0064 (13)
O3	0.0554 (18)	0.0594 (19)	0.071 (2)	−0.0112 (14)	0.0394 (16)	−0.0129 (15)
O4	0.067 (2)	0.0469 (17)	0.067 (2)	0.0100 (14)	0.0382 (17)	0.0064 (14)
O5	0.0541 (17)	0.0469 (16)	0.0389 (14)	−0.0048 (13)	0.0151 (13)	−0.0037 (12)
N1	0.0468 (17)	0.0349 (16)	0.0379 (16)	−0.0054 (13)	0.0199 (14)	−0.0032 (12)
N3	0.0431 (17)	0.0348 (16)	0.0344 (15)	−0.0011 (13)	0.0147 (13)	−0.0012 (12)
C1	0.054 (2)	0.046 (2)	0.0339 (18)	−0.0029 (17)	0.0194 (17)	0.0027 (15)
C2	0.050 (2)	0.0383 (19)	0.0363 (18)	−0.0022 (16)	0.0187 (16)	0.0012 (15)
C3	0.089 (4)	0.043 (2)	0.050 (2)	−0.006 (2)	0.032 (2)	0.0099 (19)
C4	0.096 (4)	0.034 (2)	0.067 (3)	−0.006 (2)	0.039 (3)	−0.002 (2)
C5	0.064 (3)	0.036 (2)	0.058 (2)	−0.0072 (18)	0.031 (2)	−0.0069 (18)
C6	0.096 (4)	0.041 (2)	0.078 (3)	−0.011 (2)	0.046 (3)	−0.021 (2)
C7	0.111 (5)	0.063 (3)	0.070 (3)	−0.015 (3)	0.057 (3)	−0.030 (3)
C8	0.114 (5)	0.069 (3)	0.055 (3)	−0.018 (3)	0.055 (3)	−0.016 (2)
C9	0.089 (3)	0.045 (2)	0.051 (2)	−0.012 (2)	0.042 (2)	−0.0110 (19)
C10	0.052 (2)	0.0368 (19)	0.043 (2)	−0.0080 (16)	0.0240 (18)	−0.0077 (15)
C11	0.043 (2)	0.046 (2)	0.0396 (19)	−0.0044 (16)	0.0181 (17)	−0.0102 (16)
C12	0.045 (2)	0.040 (2)	0.0386 (19)	−0.0048 (16)	0.0167 (16)	−0.0045 (15)
C13	0.064 (3)	0.044 (2)	0.056 (2)	−0.010 (2)	0.028 (2)	0.0029 (19)
C14	0.083 (3)	0.036 (2)	0.058 (3)	−0.007 (2)	0.024 (2)	0.0033 (19)
C15	0.059 (3)	0.037 (2)	0.043 (2)	0.0062 (18)	0.0070 (19)	−0.0042 (16)
C16	0.078 (3)	0.045 (3)	0.064 (3)	0.018 (2)	0.009 (3)	−0.006 (2)
C17	0.062 (3)	0.070 (3)	0.073 (3)	0.028 (3)	0.008 (3)	−0.017 (3)
C18	0.046 (3)	0.083 (4)	0.068 (3)	0.009 (2)	0.018 (2)	−0.024 (3)
C19	0.045 (2)	0.058 (3)	0.054 (2)	0.0022 (19)	0.0180 (19)	−0.011 (2)
C20	0.042 (2)	0.0378 (19)	0.0391 (19)	0.0025 (15)	0.0087 (16)	−0.0082 (15)
C21	0.061 (3)	0.075 (3)	0.093 (4)	−0.003 (2)	0.048 (3)	−0.024 (3)
C22	0.086 (4)	0.077 (3)	0.043 (2)	0.001 (3)	0.027 (2)	0.001 (2)

Geometric parameters (Å, º) top

Sn1—O1	2.083 (2)	C7—C8	1.400 (7)
Sn1—N1	2.305 (3)	C7—H7	0.9300
Sn1—Cl1	2.3838 (10)	C8—C9	1.373 (6)
Sn1—Cl3	2.3853 (11)	C8—H8	0.9300
Sn1—Cl2	2.3937 (10)	C9—C10	1.391 (6)
Sn1—Cl4	2.3947 (10)	C9—H9	0.9300
O1—C1	1.270 (5)	C11—C12	1.505 (5)
O2—C1	1.223 (4)	C12—C13	1.382 (6)
O3—C11	1.317 (5)	C13—C14	1.356 (7)
O3—C21	1.451 (6)	C13—H13	0.9300
O4—C11	1.190 (5)	C14—C15	1.404 (7)
O5—C22	1.409 (6)	C14—H14	0.9300
O5—H5	0.842 (10)	C15—C16	1.410 (6)
N1—C2	1.325 (5)	C15—C20	1.425 (6)
N1—C10	1.379 (5)	C16—C17	1.362 (8)
N3—C12	1.328 (5)	C16—H16	0.9300
N3—C20	1.364 (5)	C17—C18	1.415 (8)
N3—H3	0.860 (10)	C17—H17	0.9300
C1—C2	1.517 (5)	C18—C19	1.360 (6)
C2—C3	1.387 (6)	C18—H18	0.9300
C3—C4	1.358 (6)	C19—C20	1.397 (6)
C3—H3A	0.9300	C19—H19	0.9300
C4—C5	1.408 (6)	C21—H21A	0.9600
C4—H4	0.9300	C21—H21B	0.9600
C5—C6	1.413 (6)	C21—H21C	0.9600
C5—C10	1.423 (5)	C22—H22A	0.9600
C6—C7	1.342 (7)	C22—H22B	0.9600
C6—H6	0.9300	C22—H22C	0.9600

O1—Sn1—N1	75.66 (10)	C8—C9—C10	120.5 (4)
O1—Sn1—Cl1	86.24 (8)	C8—C9—H9	119.8
N1—Sn1—Cl1	161.86 (8)	C10—C9—H9	119.8
O1—Sn1—Cl3	88.44 (8)	N1—C10—C9	121.0 (3)
N1—Sn1—Cl3	83.31 (9)	N1—C10—C5	119.9 (3)
Cl1—Sn1—Cl3	95.15 (4)	C9—C10—C5	119.0 (4)
O1—Sn1—Cl2	179.45 (8)	O4—C11—O3	126.9 (4)
N1—Sn1—Cl2	104.89 (8)	O4—C11—C12	122.5 (4)
Cl1—Sn1—Cl2	93.21 (4)	O3—C11—C12	110.6 (3)
Cl3—Sn1—Cl2	91.59 (5)	N3—C12—C13	120.7 (4)
O1—Sn1—Cl4	88.95 (8)	N3—C12—C11	115.3 (3)
N1—Sn1—Cl4	85.89 (8)	C13—C12—C11	123.9 (4)
Cl1—Sn1—Cl4	95.12 (4)	C14—C13—C12	119.5 (4)
Cl3—Sn1—Cl4	169.21 (4)	C14—C13—H13	120.2
Cl2—Sn1—Cl4	91.12 (4)	C12—C13—H13	120.2
C1—O1—Sn1	119.0 (2)	C13—C14—C15	120.8 (4)
C11—O3—C21	116.3 (4)	C13—C14—H14	119.6
C22—O5—H5	108 (4)	C15—C14—H14	119.6
C2—N1—C10	119.0 (3)	C16—C15—C14	123.8 (5)
C2—N1—Sn1	110.0 (2)	C16—C15—C20	118.0 (5)
C10—N1—Sn1	130.7 (2)	C14—C15—C20	118.2 (4)
C12—N3—C20	122.7 (3)	C17—C16—C15	120.3 (5)
C12—N3—H3	122 (3)	C17—C16—H16	119.8
C20—N3—H3	116 (3)	C15—C16—H16	119.8
O2—C1—O1	123.4 (4)	C16—C17—C18	120.4 (4)
O2—C1—C2	118.9 (4)	C16—C17—H17	119.8
O1—C1—C2	117.6 (3)	C18—C17—H17	119.8
N1—C2—C3	123.6 (4)	C19—C18—C17	121.3 (5)
N1—C2—C1	116.4 (3)	C19—C18—H18	119.3
C3—C2—C1	120.0 (3)	C17—C18—H18	119.3
C4—C3—C2	119.0 (4)	C18—C19—C20	118.7 (5)
C4—C3—H3A	120.5	C18—C19—H19	120.6
C2—C3—H3A	120.5	C20—C19—H19	120.6
C3—C4—C5	120.0 (4)	N3—C20—C19	120.8 (4)
C3—C4—H4	120.0	N3—C20—C15	118.0 (4)
C5—C4—H4	120.0	C19—C20—C15	121.2 (4)
C4—C5—C6	123.1 (4)	O3—C21—H21A	109.5
C4—C5—C10	118.3 (4)	O3—C21—H21B	109.5
C6—C5—C10	118.6 (4)	H21A—C21—H21B	109.5
C7—C6—C5	121.0 (4)	O3—C21—H21C	109.5
C7—C6—H6	119.5	H21A—C21—H21C	109.5
C5—C6—H6	119.5	H21B—C21—H21C	109.5
C6—C7—C8	120.3 (4)	O5—C22—H22A	109.5
C6—C7—H7	119.8	O5—C22—H22B	109.5
C8—C7—H7	119.8	H22A—C22—H22B	109.5
C9—C8—C7	120.5 (5)	O5—C22—H22C	109.5
C9—C8—H8	119.8	H22A—C22—H22C	109.5
C7—C8—H8	119.8	H22B—C22—H22C	109.5

N1—Sn1—O1—C1	8.4 (3)	Sn1—N1—C10—C9	−12.5 (6)
Cl1—Sn1—O1—C1	−170.3 (3)	C2—N1—C10—C5	−4.1 (6)
Cl3—Sn1—O1—C1	−75.1 (3)	Sn1—N1—C10—C5	168.4 (3)
Cl2—Sn1—O1—C1	−169 (9)	C8—C9—C10—N1	−179.7 (5)
Cl4—Sn1—O1—C1	94.5 (3)	C8—C9—C10—C5	−0.6 (7)
O1—Sn1—N1—C2	−10.0 (3)	C4—C5—C10—N1	2.4 (7)
Cl1—Sn1—N1—C2	−6.0 (5)	C6—C5—C10—N1	−178.4 (4)
Cl3—Sn1—N1—C2	80.1 (3)	C4—C5—C10—C9	−176.7 (5)
Cl2—Sn1—N1—C2	170.0 (2)	C6—C5—C10—C9	2.5 (7)
Cl4—Sn1—N1—C2	−100.0 (3)	C21—O3—C11—O4	−2.7 (6)
O1—Sn1—N1—C10	177.0 (3)	C21—O3—C11—C12	177.7 (4)
Cl1—Sn1—N1—C10	−179.0 (2)	C20—N3—C12—C13	0.6 (6)
Cl3—Sn1—N1—C10	−92.9 (3)	C20—N3—C12—C11	−179.0 (3)
Cl2—Sn1—N1—C10	−3.0 (3)	O4—C11—C12—N3	−4.2 (6)
Cl4—Sn1—N1—C10	87.0 (3)	O3—C11—C12—N3	175.5 (3)
Sn1—O1—C1—O2	176.1 (3)	O4—C11—C12—C13	176.2 (4)
Sn1—O1—C1—C2	−5.7 (5)	O3—C11—C12—C13	−4.1 (5)
C10—N1—C2—C3	2.8 (6)	N3—C12—C13—C14	1.0 (6)
Sn1—N1—C2—C3	−171.2 (4)	C11—C12—C13—C14	−179.4 (4)
C10—N1—C2—C1	−175.6 (3)	C12—C13—C14—C15	−1.1 (7)
Sn1—N1—C2—C1	10.4 (4)	C13—C14—C15—C16	179.8 (5)
O2—C1—C2—N1	174.0 (4)	C13—C14—C15—C20	−0.5 (7)
O1—C1—C2—N1	−4.2 (6)	C14—C15—C16—C17	178.4 (5)
O2—C1—C2—C3	−4.5 (6)	C20—C15—C16—C17	−1.3 (7)
O1—C1—C2—C3	177.3 (4)	C15—C16—C17—C18	−0.2 (8)
N1—C2—C3—C4	0.4 (8)	C16—C17—C18—C19	1.2 (8)
C1—C2—C3—C4	178.8 (4)	C17—C18—C19—C20	−0.5 (7)
C2—C3—C4—C5	−2.1 (8)	C12—N3—C20—C19	177.7 (4)
C3—C4—C5—C6	−178.5 (5)	C12—N3—C20—C15	−2.1 (5)
C3—C4—C5—C10	0.8 (8)	C18—C19—C20—N3	179.2 (4)
C4—C5—C6—C7	176.3 (6)	C18—C19—C20—C15	−1.1 (6)
C10—C5—C6—C7	−2.9 (8)	C16—C15—C20—N3	−178.3 (4)
C5—C6—C7—C8	1.3 (9)	C14—C15—C20—N3	2.0 (6)
C6—C7—C8—C9	0.7 (10)	C16—C15—C20—C19	2.0 (6)
C7—C8—C9—C10	−1.0 (9)	C14—C15—C20—C19	−177.8 (4)
C2—N1—C10—C9	175.0 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2	0.84 (1)	1.95 (1)	2.785 (4)	176 (5)
N3—H3···O5	0.86 (1)	1.85 (2)	2.693 (4)	166 (4)

Experimental details

Crystal data
Chemical formula	(C₁₁H₁₀NO₂)[SnCl₄(C₁₀H₆NO₂)]·CH₄O
M_r	652.89
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.4109 (4), 33.2728 (16), 10.0241 (5)
β (°)	112.8616 (6)
V (Å³)	2584.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.44
Crystal size (mm)	0.35 × 0.25 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.633, 0.813
No. of measured, independent and observed [I > 2σ(I)] reflections	24727, 5924, 5288
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.104, 1.17
No. of reflections	5924
No. of parameters	317
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)	0.38, −1.15

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), 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
O5—H5···O2	0.84 (1)	1.95 (1)	2.785 (4)	176 (5)
N3—H3···O5	0.86 (1)	1.85 (2)	2.693 (4)	166 (4)

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, H., Yin, H. & Sun, Y. (2008). Acta Cryst. E64, m272. Web of Science CSD CrossRef IUCr Journals Google Scholar
Westrip, S. P. (2010). publCIF. In preparation. Google Scholar

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