catena-Poly[[trimethyl­tin(IV)]-μ-2-p-tolyl­acetato-κ²O:O′]

The title compound, [Sn(CH₃)₃(C₉H₉O₂)], forms polymeric chains involving both O atoms of the carboxyl­ate group. The coordination geometry around the Sn atom is distorted trigonal–bipyramidal.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.025
• wR factor = 0.065
• Data-to-parameter ratio = 26.0

checkCIF/PLATON results

No syntax errors found



Alert level B
ABSTM02_ALERT_3_B  The ratio of expected to reported Tmax/Tmin(RR') is < 0.75
            Tmin and Tmax reported:      0.461     1.000
            Tmin(prime) and Tmax expected:      0.506     0.715
            RR(prime) =      0.651
            Please check that your absorption correction is appropriate.
PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large .............       0.64

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.71
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          4
            O2  -SN  -O1  -C1    173.80  0.50   2.555   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          9

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      0.715
            Tmax scaled      0.715 Tmin scaled      0.330

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

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

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Computing details

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2000); software used to prepare material for publication: SHELXTL.

catena-Poly[[trimethyltin(IV)]-2-p-tolylacetato-κ²O:O']

Crystal data

[Sn(CH3)3(C9H9O2)]	F(000) = 624
Mr = 312.95	Dx = 1.576 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9925 reflections
a = 10.835 (2) Å	θ = 2.6–29.7°
b = 9.925 (2) Å	µ = 1.92 mm^−1
c = 12.304 (3) Å	T = 173 K
β = 94.635 (2)°	Block, colorless
V = 1318.8 (5) Å^3	0.35 × 0.18 × 0.18 mm
Z = 4

Data collection

Bruker APEX-2 CCD area-detector diffractometer	3636 independent reflections
Radiation source: fine-focus sealed tube	3429 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
φ and ω scans	θmax = 29.7°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −14→15
Tmin = 0.461, Tmax = 1.000	k = −11→13
13867 measured reflections	l = −16→16

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)] = 0.025	H-atom parameters constrained
wR(F^2) = 0.065	w = 1/[σ^2(Fo^2) + (0.0286P)^2 + 0.7943P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
3636 reflections	Δρmax = 0.90 e Å^−3
140 parameters	Δρmin = −1.16 e Å^−3
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0356 (16)

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	Uiso*/Ueq
Sn	0.064251 (11)	0.186357 (13)	0.228840 (9)	0.02106 (8)
O1	0.18973 (14)	0.02933 (14)	0.17639 (12)	0.0271 (3)
O2	0.05565 (14)	−0.12621 (17)	0.21783 (13)	0.0302 (3)
C1	0.15799 (18)	−0.0935 (2)	0.18650 (16)	0.0235 (4)
C2	0.2527 (2)	−0.1982 (2)	0.16043 (19)	0.0301 (4)
H2A	0.2972	−0.1662	0.0982	0.036*
H2B	0.2092	−0.2826	0.1378	0.036*
C3	0.34656 (18)	−0.2282 (2)	0.25609 (17)	0.0261 (4)
C4	0.3680 (2)	−0.1412 (3)	0.3447 (2)	0.0369 (5)
H4A	0.3232	−0.0591	0.3466	0.044*
C5	0.4547 (3)	−0.1740 (3)	0.4303 (2)	0.0402 (6)
H5A	0.4670	−0.1142	0.4905	0.048*
C6	0.5236 (2)	−0.2916 (3)	0.4300 (2)	0.0378 (5)
C7	0.5026 (2)	−0.3775 (3)	0.3415 (2)	0.0399 (5)
H7A	0.5490	−0.4585	0.3389	0.048*
C8	0.4150 (2)	−0.3467 (3)	0.2566 (2)	0.0340 (5)
H8A	0.4014	−0.4080	0.1976	0.041*
C9	0.6188 (3)	−0.3241 (4)	0.5228 (3)	0.0564 (9)
H9A	0.6937	−0.3596	0.4935	0.085*
H9B	0.5852	−0.3916	0.5705	0.085*
H9C	0.6394	−0.2420	0.5648	0.085*
C1A	0.0652 (2)	0.1169 (2)	0.39218 (17)	0.0335 (5)
H1AA	0.0726	0.1939	0.4421	0.050*
H1AB	0.1355	0.0559	0.4081	0.050*
H1AC	−0.0122	0.0687	0.4017	0.050*
C2A	−0.0803 (2)	0.1452 (3)	0.10658 (17)	0.0315 (4)
H2AA	−0.1152	0.2302	0.0776	0.047*
H2AB	−0.1451	0.0927	0.1381	0.047*
H2AC	−0.0472	0.0937	0.0475	0.047*
C3A	0.1977 (2)	0.3370 (2)	0.1996 (2)	0.0306 (4)
H3AA	0.2002	0.4042	0.2581	0.046*
H3AB	0.1748	0.3809	0.1295	0.046*
H3AC	0.2794	0.2951	0.1978	0.046*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn	0.02345 (10)	0.02102 (10)	0.01867 (9)	−0.00050 (4)	0.00143 (5)	0.00093 (4)
O1	0.0251 (7)	0.0226 (7)	0.0343 (7)	−0.0002 (5)	0.0069 (6)	−0.0005 (6)
O2	0.0282 (7)	0.0246 (8)	0.0388 (8)	−0.0016 (6)	0.0079 (6)	0.0033 (6)
C1	0.0240 (8)	0.0232 (9)	0.0230 (8)	0.0017 (7)	−0.0005 (7)	−0.0016 (7)
C2	0.0288 (10)	0.0286 (11)	0.0322 (11)	0.0051 (8)	−0.0016 (8)	−0.0080 (8)
C3	0.0223 (8)	0.0258 (10)	0.0306 (9)	−0.0009 (7)	0.0034 (7)	−0.0003 (8)
C4	0.0412 (12)	0.0299 (11)	0.0382 (12)	0.0057 (10)	−0.0053 (10)	−0.0052 (9)
C5	0.0422 (14)	0.0408 (14)	0.0363 (13)	−0.0061 (10)	−0.0047 (11)	−0.0025 (9)
C6	0.0245 (10)	0.0516 (14)	0.0370 (12)	−0.0023 (9)	0.0019 (9)	0.0155 (10)
C7	0.0332 (11)	0.0410 (14)	0.0458 (13)	0.0123 (10)	0.0047 (10)	0.0093 (11)
C8	0.0292 (10)	0.0331 (11)	0.0399 (12)	0.0069 (9)	0.0049 (9)	−0.0036 (9)
C9	0.0384 (15)	0.084 (3)	0.0447 (16)	0.0002 (14)	−0.0074 (12)	0.0204 (14)
C1A	0.0423 (12)	0.0363 (12)	0.0220 (9)	0.0056 (10)	0.0029 (8)	0.0040 (8)
C2A	0.0327 (10)	0.0348 (11)	0.0258 (10)	0.0014 (9)	−0.0049 (8)	0.0001 (9)
C3A	0.0298 (10)	0.0281 (10)	0.0347 (11)	−0.0042 (8)	0.0067 (9)	−0.0006 (8)

Geometric parameters (Å, º)

Sn—C2A	2.121 (2)	C6—C7	1.387 (4)
Sn—C1A	2.124 (2)	C6—C9	1.511 (4)
Sn—C3A	2.130 (2)	C7—C8	1.388 (3)
Sn—O1	2.1989 (15)	C7—H7A	0.9500
Sn—O2^i	2.3909 (16)	C8—H8A	0.9500
O1—C1	1.276 (2)	C9—H9A	0.9800
O2—C1	1.246 (2)	C9—H9B	0.9800
O2—Sn^ii	2.3909 (16)	C9—H9C	0.9800
C1—C2	1.513 (3)	C1A—H1AA	0.9800
C2—C3	1.521 (3)	C1A—H1AB	0.9800
C2—H2A	0.9900	C1A—H1AC	0.9800
C2—H2B	0.9900	C2A—H2AA	0.9800
C3—C8	1.389 (3)	C2A—H2AB	0.9800
C3—C4	1.395 (3)	C2A—H2AC	0.9800
C4—C5	1.393 (4)	C3A—H3AA	0.9800
C4—H4A	0.9500	C3A—H3AB	0.9800
C5—C6	1.385 (4)	C3A—H3AC	0.9800
C5—H5A	0.9500
C2A—Sn—C1A	123.72 (10)	C7—C6—C9	121.4 (3)
C2A—Sn—C3A	119.17 (9)	C6—C7—C8	120.9 (2)
C1A—Sn—C3A	115.86 (10)	C6—C7—H7A	119.5
C2A—Sn—O1	95.39 (8)	C8—C7—H7A	119.5
C1A—Sn—O1	95.27 (8)	C7—C8—C3	121.5 (2)
C3A—Sn—O1	90.21 (8)	C7—C8—H8A	119.3
C2A—Sn—O2^i	87.60 (8)	C3—C8—H8A	119.3
C1A—Sn—O2^i	87.37 (8)	C6—C9—H9A	109.5
C3A—Sn—O2^i	83.78 (8)	C6—C9—H9B	109.5
O1—Sn—O2^i	173.99 (5)	H9A—C9—H9B	109.5
C1—O1—Sn	118.09 (12)	C6—C9—H9C	109.5
C1—O2—Sn^ii	143.55 (14)	H9A—C9—H9C	109.5
O2—C1—O1	122.19 (18)	H9B—C9—H9C	109.5
O2—C1—C2	121.52 (19)	Sn—C1A—H1AA	109.5
O1—C1—C2	116.28 (18)	Sn—C1A—H1AB	109.5
C1—C2—C3	113.14 (18)	H1AA—C1A—H1AB	109.5
C1—C2—H2A	109.0	Sn—C1A—H1AC	109.5
C3—C2—H2A	109.0	H1AA—C1A—H1AC	109.5
C1—C2—H2B	109.0	H1AB—C1A—H1AC	109.5
C3—C2—H2B	109.0	Sn—C2A—H2AA	109.5
H2A—C2—H2B	107.8	Sn—C2A—H2AB	109.5
C8—C3—C4	117.7 (2)	H2AA—C2A—H2AB	109.5
C8—C3—C2	119.48 (19)	Sn—C2A—H2AC	109.5
C4—C3—C2	122.8 (2)	H2AA—C2A—H2AC	109.5
C5—C4—C3	120.4 (2)	H2AB—C2A—H2AC	109.5
C5—C4—H4A	119.8	Sn—C3A—H3AA	109.5
C3—C4—H4A	119.8	Sn—C3A—H3AB	109.5
C6—C5—C4	121.7 (2)	H3AA—C3A—H3AB	109.5
C6—C5—H5A	119.2	Sn—C3A—H3AC	109.5
C4—C5—H5A	119.2	H3AA—C3A—H3AC	109.5
C5—C6—C7	117.8 (2)	H3AB—C3A—H3AC	109.5
C5—C6—C9	120.8 (3)
C2A—Sn—O1—C1	−66.63 (16)	C1—C2—C3—C4	−19.1 (3)
C1A—Sn—O1—C1	58.02 (16)	C8—C3—C4—C5	−0.4 (4)
C3A—Sn—O1—C1	174.03 (15)	C2—C3—C4—C5	179.7 (2)
O2^i—Sn—O1—C1	173.8 (5)	C3—C4—C5—C6	1.1 (4)
Sn^ii—O2—C1—O1	−172.63 (15)	C4—C5—C6—C7	−0.6 (4)
Sn^ii—O2—C1—C2	6.1 (3)	C4—C5—C6—C9	178.9 (3)
Sn—O1—C1—O2	4.9 (3)	C5—C6—C7—C8	−0.4 (4)
Sn—O1—C1—C2	−173.90 (13)	C9—C6—C7—C8	−180.0 (3)
O2—C1—C2—C3	−94.4 (2)	C6—C7—C8—C3	1.1 (4)
O1—C1—C2—C3	84.4 (2)	C4—C3—C8—C7	−0.7 (4)
C1—C2—C3—C8	161.1 (2)	C2—C3—C8—C7	179.2 (2)

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