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

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.021
• wR factor = 0.055
• Data-to-parameter ratio = 15.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.92
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Sn1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Sn2

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.921
            Tmax scaled      0.504 Tmin scaled      0.428
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           25.00
           From the CIF: _reflns_number_total               2439
           Count of symmetry unique reflns         1402
           Completeness (_total/calc)            173.97%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1037
           Fraction of Friedel pairs measured     0.740
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

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

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)

S2. Experimental

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.

S3. Refinement

H atoms were positioned geometrically, with C—H = 0.93 and 0.96 Å for aromatic and methyl H atoms, respectively, and constrained to ride on their parent atoms, with U_iso(H) = xU_eq(C) where x = 1.5 for methyl H and x = 1.2 for aromatic H atoms.

Computing details

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

	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]

Crystal data

[Sn(CH3)3(C10H6NO2)]	F(000) = 1328
Mr = 335.95	Dx = 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) Å^3	Block, colourless
Z = 8	0.49 × 0.48 × 0.37 mm

Data collection

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

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.021	H-atom parameters constrained
wR(F^2) = 0.055	w = 1/[σ^2(Fo^2) + (0.0295P)^2 + 1.3697P] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2439 reflections	Δρmax = 0.40 e Å^−3
156 parameters	Δρmin = −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)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Sn1—C12	2.113 (5)	C5—C10	1.418 (6)
Sn1—C11^i	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—O1^i	2.267 (2)	C8—C9	1.392 (9)
Sn2—C14^ii	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—O2^ii	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—C11^i	121.36 (18)	N1—C6—C7	118.4 (4)
C12—Sn1—C11	121.36 (18)	C5—C6—C7	119.5 (4)
C11^i—Sn1—C11	117.3 (4)	C8—C7—C6	119.6 (5)
C12—Sn1—O1	92.29 (7)	C8—C7—H7	120.2
C11^i—Sn1—O1	85.04 (13)	C6—C7—H7	120.2
C11—Sn1—O1	92.56 (14)	C7—C8—C9	120.6 (5)
C12—Sn1—O1^i	92.29 (7)	C7—C8—H8	119.7
C11^i—Sn1—O1^i	92.56 (14)	C9—C8—H8	119.7
C11—Sn1—O1^i	85.04 (13)	C10—C9—C8	121.2 (4)
O1—Sn1—O1^i	175.41 (15)	C10—C9—H9	119.4
C14^ii—Sn2—C14	131.0 (3)	C8—C9—H9	119.4
C14^ii—Sn2—C13	114.51 (14)	C9—C10—C5	120.0 (5)
C14—Sn2—C13	114.51 (14)	C9—C10—H10	120.0
C14^ii—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
C14^ii—Sn2—O2^ii	93.37 (18)	H11A—C11—H11B	109.5
C14—Sn2—O2^ii	90.63 (17)	Sn1—C11—H11C	109.5
C13—Sn2—O2^ii	85.17 (7)	H11A—C11—H11C	109.5
O2—Sn2—O2^ii	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.