catena-Poly[[trimethyl­tin(IV)]-μ-quinaldato]

Wang, H.; Yin, H.; Wang, D.

doi:10.1107/S1600536807061715

metal-organic compounds

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Volume 64| Part 1| January 2008| Page m26

https://doi.org/10.1107/S1600536807061715

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catena-Poly[[trimethyltin(IV)]-μ-quinaldato]

Hongyun Wang,^a Handong Yin ^a ^* and Daqi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 13 November 2007; accepted 21 November 2007; online 6 December 2007)

The title compound, [Sn(CH₃)₃(C₁₀H₆NO₂)]_n, forms an extended one-dimensional chain structure. There are two independent Sn^IV ions, both of which are in slightly distorted trigonal-bipyramidal coordination environments with two symmetry-related O atoms in the axial sites. In each case, the Sn^IV ion and one of the three equatorial C atoms lie on a crystallographic twofold axis.

Related literature

A series of new triorganotin(IV) pyridinedicarboxylates has been synthesized by the reaction of trimethyltin(IV), triphenyltin(IV) or tribenzyltin(IV) chloride with 2,6(3,5 or 2,5)-H₂pdc (pdc = pyridinedicarboxylate), see: Ma et al. (2006 )

Experimental

Crystal data

[Sn(CH₃)₃(C₁₀H₆NO₂)]
M_r = 335.95
Orthorhombic, C 222₁
a = 7.0487 (14) Å
b = 25.011 (2) Å
c = 15.587 (2) Å
V = 2748.0 (7) Å³
Z = 8
Mo Kα radiation
μ = 1.85 mm⁻¹
T = 298 (2) K
0.49 × 0.48 × 0.37 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.464, T_max = 0.548 (expected range = 0.428–0.504)
7068 measured reflections
2439 independent reflections
2251 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.021
wR(F²) = 0.055
S = 1.00
2439 reflections
156 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.24 e Å⁻³
Absolute structure: Flack (1983 ), 1036 Friedel pairs
Flack parameter: −0.06 (3)

Table 1
Selected geometric parameters (Å, °)

Sn1—C12	2.113 (5)
Sn1—C11	2.118 (4)
Sn1—O1	2.267 (2)
Sn2—C14	2.100 (5)
Sn2—C13	2.134 (4)
Sn2—O2	2.281 (3)

C12—Sn1—C11	121.36 (18)
C11ⁱ—Sn1—C11	117.3 (4)
O1—Sn1—O1ⁱ	175.41 (15)
C14ⁱⁱ—Sn2—C14	131.0 (3)
C14—Sn2—C13	114.51 (14)
O2—Sn2—O2ⁱⁱ	170.34 (14)
Symmetry codes: (i) x, -y+1, -z+1; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b ); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807061715/lh2573sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807061715/lh2573Isup2.hkl

checkCIF report

Comment top

Organotin esters of carboxylic acids are widely used as biocides, fungicides and in industry as homogeneous catalysts. Studies on organotin complexes containing carboxylate ligands with an additional donor atom (e.g N, O or S) that is available for coordinating to an Sn atom have revealed that new structural types may lead to different activities. We have therefore synthesized the title compound, (I), and present its crystal structure here. The title compound, (Fig. 1), forms an extended one-dimensional chain structure arising from Sn—O bridges to ligands. The Sn—O distances in (I) (Table 1), are similar to those in related organotin carboxylates (Ma et al., 2006). The two independent Sn^IV atoms are in slightly distorted trigonal-bipyramidal coordination geometries, with the O atoms in axial positions and three C atoms of three methyl groups in equatorial positions.

Related literature top

Experimental top

The reaction was carried out under N₂ atmosphere. Quinaldic acid (1 mmol) and sodium ethoxide (1.2 mmol) were added to benzene(30 ml) in a Schlenk flask and stirred for 0.5 h. Trimethyltin chloride (1 mmol) was then added to the reactor and the reaction mixture was stirred for 12 h at 313 K. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixture of dichloromethane/methanol (1:1).(yield 83%; m.p. 447 K). Analysis calculated (%) for C₁₃H₁₅NO₂Sn (Mr = 335.95): C, 46.47; H, 4.50; N, 4.17. found: C, 46.39; H, 4.62; N, 4.21.

Structure description top

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).

Figures top

	Fig. 1. The molecular structure showing 50% probability displacement ellipsoids and the atom-numbering scheme. H atoms have been omitted for clarity [symmetry code: (A) x, -y + 1, -z + 1; (B) -x + 1, y, -z + 1/2].
	Fig. 2. The extended chain structure of with H atoms omitted for clarity.

catena-Poly[[trimethyltin(IV)]-µ-quinaldato] top

Crystal data top

[Sn(CH₃)₃(C₁₀H₆NO₂)]	F(000) = 1328
M_r = 335.95	D_x = 1.624 Mg m⁻³
Orthorhombic, C222₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2c 2	Cell parameters from 5374 reflections
a = 7.0487 (14) Å	θ = 2.6–28.0°
b = 25.011 (2) Å	µ = 1.85 mm⁻¹
c = 15.587 (2) Å	T = 298 K
V = 2748.0 (7) Å³	Block, colourless
Z = 8	0.49 × 0.48 × 0.37 mm

Data collection top

Bruker SMART CCD diffractometer	2439 independent reflections
Radiation source: fine-focus sealed tube	2251 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
φ and ω scans	θ_max = 25.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
T_min = 0.464, T_max = 0.548	k = −29→29
7068 measured reflections	l = −9→18

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.055	w = 1/[σ²(F_o²) + (0.0295P)² + 1.3697P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2439 reflections	Δρ_max = 0.40 e Å⁻³
156 parameters	Δρ_min = −0.24 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1036 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.06 (3)

Crystal data top

[Sn(CH₃)₃(C₁₀H₆NO₂)]	V = 2748.0 (7) Å³
M_r = 335.95	Z = 8
Orthorhombic, C222₁	Mo Kα radiation
a = 7.0487 (14) Å	µ = 1.85 mm⁻¹
b = 25.011 (2) Å	T = 298 K
c = 15.587 (2) Å	0.49 × 0.48 × 0.37 mm

Data collection top

Bruker SMART CCD diffractometer	2439 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2251 reflections with I > 2σ(I)
T_min = 0.464, T_max = 0.548	R_int = 0.035
7068 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.055	Δρ_max = 0.40 e Å⁻³
S = 1.00	Δρ_min = −0.24 e Å⁻³
2439 reflections	Absolute structure: Flack (1983), 1036 Friedel pairs
156 parameters	Absolute structure parameter: −0.06 (3)
0 restraints

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Sn1	0.85035 (5)	0.5000	0.5000	0.04229 (10)
Sn2	0.5000	0.597822 (12)	0.2500	0.04016 (10)
N1	0.7684 (4)	0.69843 (12)	0.3468 (2)	0.0435 (7)
O1	0.8632 (4)	0.58995 (10)	0.48310 (17)	0.0540 (7)
O2	0.7139 (4)	0.59014 (11)	0.35911 (18)	0.0558 (7)
C1	0.7965 (6)	0.61356 (14)	0.4183 (2)	0.0425 (9)
C2	0.8264 (5)	0.67348 (14)	0.4162 (2)	0.0398 (8)
C3	0.9083 (5)	0.69858 (14)	0.4871 (3)	0.0480 (9)
H3	0.9465	0.6786	0.5344	0.058*
C4	0.9317 (6)	0.75282 (14)	0.4862 (4)	0.0557 (12)
H4	0.9858	0.7704	0.5327	0.067*
C5	0.8716 (6)	0.78169 (15)	0.4128 (3)	0.0520 (10)
C6	0.7940 (6)	0.75296 (15)	0.3438 (3)	0.0455 (9)
C7	0.7360 (7)	0.78067 (17)	0.2691 (3)	0.0655 (13)
H7	0.6860	0.7620	0.2227	0.079*
C8	0.7539 (7)	0.83512 (19)	0.2655 (5)	0.0775 (17)
H8	0.7158	0.8534	0.2165	0.093*
C9	0.8285 (9)	0.86342 (19)	0.3346 (4)	0.0766 (16)
H9	0.8371	0.9005	0.3315	0.092*
C10	0.8888 (7)	0.83802 (17)	0.4062 (4)	0.0686 (14)
H10	0.9416	0.8575	0.4510	0.082*
C11	1.0067 (9)	0.48610 (17)	0.3861 (3)	0.0718 (13)
H11A	1.1400	0.4876	0.3986	0.108*
H11B	0.9756	0.5130	0.3445	0.108*
H11C	0.9755	0.4514	0.3638	0.108*
C12	0.5506 (8)	0.5000	0.5000	0.0627 (15)
H12A	0.5052	0.4932	0.4430	0.094*	0.50
H12B	0.5052	0.5342	0.5191	0.094*	0.50
H12C	0.5052	0.4726	0.5380	0.094*	0.50
C13	0.5000	0.51249 (17)	0.2500	0.0531 (13)
H13A	0.5943	0.4997	0.2106	0.080*	0.50
H13B	0.3774	0.4997	0.2328	0.080*	0.50
H13C	0.5283	0.4997	0.3066	0.080*	0.50
C14	0.6981 (9)	0.63265 (19)	0.1663 (3)	0.0655 (14)
H14A	0.7675	0.6050	0.1372	0.098*
H14B	0.7844	0.6545	0.1985	0.098*
H14C	0.6328	0.6543	0.1249	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.04158 (19)	0.04241 (18)	0.04287 (19)	0.000	0.000	0.00532 (19)
Sn2	0.0528 (2)	0.03181 (16)	0.03584 (17)	0.000	0.00173 (17)	0.000
N1	0.0400 (17)	0.0416 (16)	0.0489 (18)	0.0011 (14)	−0.0024 (13)	0.0032 (15)
O1	0.0703 (17)	0.0394 (13)	0.0524 (17)	−0.0040 (12)	−0.0230 (15)	0.0057 (12)
O2	0.0699 (19)	0.0420 (15)	0.0554 (17)	−0.0057 (14)	−0.0224 (15)	0.0013 (13)
C1	0.046 (2)	0.0386 (18)	0.043 (2)	0.0006 (16)	−0.0050 (18)	0.0004 (16)
C2	0.037 (2)	0.0371 (17)	0.045 (2)	0.0010 (16)	−0.0021 (16)	0.0000 (16)
C3	0.052 (2)	0.0444 (19)	0.048 (2)	0.0020 (16)	−0.0093 (19)	0.0040 (19)
C4	0.060 (3)	0.0467 (19)	0.061 (3)	−0.0059 (18)	−0.009 (2)	−0.008 (2)
C5	0.045 (2)	0.041 (2)	0.071 (3)	−0.0004 (18)	0.011 (2)	−0.004 (2)
C6	0.037 (2)	0.0382 (19)	0.061 (3)	0.0052 (16)	0.0081 (19)	0.0097 (18)
C7	0.060 (3)	0.060 (2)	0.076 (4)	0.006 (2)	−0.003 (2)	0.020 (2)
C8	0.063 (3)	0.058 (3)	0.111 (5)	0.009 (2)	0.002 (3)	0.036 (3)
C9	0.064 (4)	0.043 (2)	0.122 (5)	0.001 (2)	0.013 (4)	0.018 (3)
C10	0.068 (3)	0.040 (2)	0.097 (4)	−0.007 (2)	0.015 (3)	−0.008 (2)
C11	0.077 (3)	0.067 (3)	0.072 (3)	0.010 (3)	0.034 (3)	0.012 (2)
C12	0.044 (3)	0.079 (4)	0.065 (3)	0.000	0.000	0.018 (4)
C13	0.070 (4)	0.036 (3)	0.054 (3)	0.000	−0.009 (3)	0.000
C14	0.078 (4)	0.066 (3)	0.052 (3)	−0.008 (3)	0.017 (3)	0.007 (2)

Geometric parameters (Å, º) top

Sn1—C12	2.113 (5)	C5—C10	1.418 (6)
Sn1—C11ⁱ	2.118 (4)	C6—C7	1.415 (6)
Sn1—C11	2.118 (4)	C7—C8	1.369 (6)
Sn1—O1	2.267 (2)	C7—H7	0.9300
Sn1—O1ⁱ	2.267 (2)	C8—C9	1.392 (9)
Sn2—C14ⁱⁱ	2.100 (5)	C8—H8	0.9300
Sn2—C14	2.100 (5)	C9—C10	1.352 (8)
Sn2—C13	2.134 (4)	C9—H9	0.9300
Sn2—O2	2.281 (3)	C10—H10	0.9300
Sn2—O2ⁱⁱ	2.281 (3)	C11—H11A	0.9600
N1—C2	1.315 (5)	C11—H11B	0.9600
N1—C6	1.377 (5)	C11—H11C	0.9600
O1—C1	1.261 (4)	C12—H12A	0.9600
O2—C1	1.238 (5)	C12—H12B	0.9600
C1—C2	1.514 (5)	C12—H12C	0.9600
C2—C3	1.395 (5)	C13—H13A	0.9600
C3—C4	1.367 (5)	C13—H13B	0.9600
C3—H3	0.9300	C13—H13C	0.9600
C4—C5	1.418 (7)	C14—H14A	0.9600
C4—H4	0.9300	C14—H14B	0.9600
C5—C6	1.404 (6)	C14—H14C	0.9600

C12—Sn1—C11ⁱ	121.36 (18)	N1—C6—C7	118.4 (4)
C12—Sn1—C11	121.36 (18)	C5—C6—C7	119.5 (4)
C11ⁱ—Sn1—C11	117.3 (4)	C8—C7—C6	119.6 (5)
C12—Sn1—O1	92.29 (7)	C8—C7—H7	120.2
C11ⁱ—Sn1—O1	85.04 (13)	C6—C7—H7	120.2
C11—Sn1—O1	92.56 (14)	C7—C8—C9	120.6 (5)
C12—Sn1—O1ⁱ	92.29 (7)	C7—C8—H8	119.7
C11ⁱ—Sn1—O1ⁱ	92.56 (14)	C9—C8—H8	119.7
C11—Sn1—O1ⁱ	85.04 (13)	C10—C9—C8	121.2 (4)
O1—Sn1—O1ⁱ	175.41 (15)	C10—C9—H9	119.4
C14ⁱⁱ—Sn2—C14	131.0 (3)	C8—C9—H9	119.4
C14ⁱⁱ—Sn2—C13	114.51 (14)	C9—C10—C5	120.0 (5)
C14—Sn2—C13	114.51 (14)	C9—C10—H10	120.0
C14ⁱⁱ—Sn2—O2	90.63 (17)	C5—C10—H10	120.0
C14—Sn2—O2	93.37 (18)	Sn1—C11—H11A	109.5
C13—Sn2—O2	85.17 (7)	Sn1—C11—H11B	109.5
C14ⁱⁱ—Sn2—O2ⁱⁱ	93.37 (18)	H11A—C11—H11B	109.5
C14—Sn2—O2ⁱⁱ	90.63 (17)	Sn1—C11—H11C	109.5
C13—Sn2—O2ⁱⁱ	85.17 (7)	H11A—C11—H11C	109.5
O2—Sn2—O2ⁱⁱ	170.34 (14)	H11B—C11—H11C	109.5
C2—N1—C6	117.2 (3)	Sn1—C12—H12A	109.5
C1—O1—Sn1	122.9 (2)	Sn1—C12—H12B	109.5
C1—O2—Sn2	145.8 (3)	H12A—C12—H12B	109.5
O2—C1—O1	123.4 (3)	Sn1—C12—H12C	109.5
O2—C1—C2	121.2 (3)	H12A—C12—H12C	109.5
O1—C1—C2	115.4 (3)	H12B—C12—H12C	109.5
N1—C2—C3	124.5 (3)	Sn2—C13—H13A	109.5
N1—C2—C1	116.4 (3)	Sn2—C13—H13B	109.5
C3—C2—C1	119.1 (3)	H13A—C13—H13B	109.5
C4—C3—C2	119.2 (4)	Sn2—C13—H13C	109.5
C4—C3—H3	120.4	H13A—C13—H13C	109.5
C2—C3—H3	120.4	H13B—C13—H13C	109.5
C3—C4—C5	118.5 (4)	Sn2—C14—H14A	109.5
C3—C4—H4	120.7	Sn2—C14—H14B	109.5
C5—C4—H4	120.7	H14A—C14—H14B	109.5
C6—C5—C4	118.3 (3)	Sn2—C14—H14C	109.5
C6—C5—C10	119.1 (4)	H14A—C14—H14C	109.5
C4—C5—C10	122.6 (4)	H14B—C14—H14C	109.5
N1—C6—C5	122.1 (4)

Symmetry codes: (i) x, −y+1, −z+1; (ii) −x+1, y, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Sn(CH₃)₃(C₁₀H₆NO₂)]
M_r	335.95
Crystal system, space group	Orthorhombic, C222₁
Temperature (K)	298
a, b, c (Å)	7.0487 (14), 25.011 (2), 15.587 (2)
V (Å³)	2748.0 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	1.85
Crystal size (mm)	0.49 × 0.48 × 0.37

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.464, 0.548
No. of measured, independent and observed [I > 2σ(I)] reflections	7068, 2439, 2251
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.055, 1.00
No. of reflections	2439
No. of parameters	156
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.24
Absolute structure	Flack (1983), 1036 Friedel pairs
Absolute structure parameter	−0.06 (3)

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).

Selected geometric parameters (Å, º) top

Sn1—C12	2.113 (5)	Sn2—C14	2.100 (5)
Sn1—C11	2.118 (4)	Sn2—C13	2.134 (4)
Sn1—O1	2.267 (2)	Sn2—O2	2.281 (3)

C12—Sn1—C11	121.36 (18)	C14ⁱⁱ—Sn2—C14	131.0 (3)
C11ⁱ—Sn1—C11	117.3 (4)	C14—Sn2—C13	114.51 (14)
O1—Sn1—O1ⁱ	175.41 (15)	O2—Sn2—O2ⁱⁱ	170.34 (14)

Symmetry codes: (i) x, −y+1, −z+1; (ii) −x+1, y, −z+1/2.

Acknowledgements

We thank the National Natural Science Foundation of China (20771053) and the Natural Science Foundation of Shandong Province (2005ZX09) for financial support.

References

Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Ma, C., Li, J., Zhang, R. & Wang, D. (2006). J. Organomet. Chem. 691, 1713–1721. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997a). SHELXL97 and SHELXS97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997b). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-Ray Systems, Inc., Madison, Wisconsin, USA. Google Scholar