catena-Poly[[dibutyl­tin(IV)]-μ-3,4,5,6-tetra­fluoro­benzene-1,2-dicarboxyl­ato-κ⁴O¹,O^1′:O²,O^2′]

The crystal structure determination of the title compound, [Sn(C₄H₉)₂(C₈F₄O₄)]_n, revealed an infinite polymeric chain in the solid state. The Sn atom is in a distorted sixfold coordination between bicapped tetrahedral and skew-bipyramidal.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.014 Å
• R factor = 0.055
• wR factor = 0.184
• Data-to-parameter ratio = 14.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.00 Ratio
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         14

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1999); 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.

catena-Poly[[dibutyltin(IV)]-µ-3,4,5,6-tetrafluorobenzene-1,2-dicarboxylato- κ⁴O¹,O^1':O²,O^2']

Crystal data

[Sn(C4H9)2(C8F4O4)]	F(000) = 928
Mr = 468.99	Dx = 1.663 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.8470 (17) Å	Cell parameters from 3138 reflections
b = 17.733 (3) Å	θ = 2.2–25.6°
c = 11.146 (2) Å	µ = 1.42 mm^−1
β = 105.732 (3)°	T = 298 K
V = 1873.3 (6) Å^3	Block, colourless
Z = 4	0.23 × 0.21 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3238 independent reflections
Radiation source: fine-focus sealed tube	2125 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→11
Tmin = 0.736, Tmax = 0.815	k = −21→21
9445 measured reflections	l = −13→13

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.184	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.121P)^2 + 0.7607P] where P = (Fo^2 + 2Fc^2)/3
3238 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.97 e Å^−3
376 restraints	Δρmin = −1.22 e Å^−3

Special details

Experimental. The elemental analyses were performed with PERKIN ELMER MODEL 2400 SERIES II.

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
Sn1	0.53223 (7)	0.19966 (3)	0.14262 (5)	0.0682 (3)
F1	0.3152 (7)	−0.0370 (3)	0.2338 (5)	0.1068 (19)
F2	0.1551 (7)	−0.1018 (3)	0.3641 (6)	0.1124 (19)
F3	0.1259 (6)	−0.0376 (3)	0.5742 (6)	0.1044 (18)
F4	0.2610 (7)	0.0900 (3)	0.6573 (5)	0.1004 (18)
O1	0.4000 (6)	0.1622 (3)	0.2470 (4)	0.0653 (13)
O2	0.5585 (7)	0.0710 (3)	0.2748 (5)	0.0831 (16)
O3	0.5552 (6)	0.1795 (3)	0.5122 (5)	0.0715 (14)
O4	0.3898 (7)	0.2097 (3)	0.6020 (5)	0.0747 (15)
C1	0.4561 (10)	0.0987 (5)	0.2964 (7)	0.0700 (14)
C2	0.3763 (9)	0.0620 (4)	0.3786 (6)	0.0630 (15)
C3	0.3062 (9)	−0.0040 (4)	0.3392 (7)	0.0701 (16)
C4	0.2217 (9)	−0.0372 (4)	0.4045 (7)	0.0733 (17)
C5	0.2073 (9)	−0.0040 (5)	0.5108 (8)	0.0712 (16)
C6	0.2767 (9)	0.0609 (4)	0.5513 (7)	0.0683 (16)
C7	0.3607 (8)	0.0950 (4)	0.4875 (6)	0.0596 (15)
C8	0.4430 (10)	0.1659 (4)	0.5342 (7)	0.0650 (15)
C9	0.7078 (11)	0.2375 (6)	0.2756 (10)	0.098 (2)
H9A	0.7105	0.2921	0.2810	0.118*
H9B	0.7139	0.2163	0.3570	0.118*
C10	0.8273 (12)	0.2053 (7)	0.2183 (13)	0.121 (3)
H10A	0.8120	0.1521	0.1996	0.146*
H10B	0.8263	0.2318	0.1418	0.146*
C11	0.9663 (12)	0.2172 (8)	0.3142 (14)	0.139 (3)
H11A	0.9694	0.1882	0.3888	0.167*
H11B	0.9787	0.2701	0.3368	0.167*
C12	1.0845 (16)	0.1906 (9)	0.2558 (19)	0.179 (6)
H12A	1.1750	0.2026	0.3112	0.268*
H12B	1.0742	0.2158	0.1775	0.268*
H12C	1.0775	0.1371	0.2425	0.268*
C13	0.4925 (10)	0.1354 (5)	−0.0233 (9)	0.0896 (19)
H13A	0.4703	0.1697	−0.0938	0.108*
H13B	0.5782	0.1088	−0.0244	0.108*
C14	0.3719 (9)	0.0775 (5)	−0.0410 (8)	0.0891 (19)
H14A	0.3714	0.0455	−0.1117	0.107*
H14B	0.3891	0.0457	0.0324	0.107*
C15	0.2331 (10)	0.1137 (6)	−0.0617 (10)	0.104 (2)
H15A	0.2189	0.1482	−0.1315	0.124*
H15B	0.2317	0.1430	0.0115	0.124*
C16	0.1109 (12)	0.0563 (8)	−0.0883 (12)	0.140 (4)
H16A	0.0229	0.0826	−0.1021	0.210*
H16B	0.1227	0.0231	−0.0182	0.210*
H16C	0.1113	0.0274	−0.1611	0.210*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0944 (5)	0.0617 (4)	0.0577 (4)	0.0113 (3)	0.0365 (3)	0.0098 (2)
F1	0.178 (6)	0.072 (3)	0.071 (3)	−0.011 (3)	0.034 (3)	−0.024 (2)
F2	0.127 (5)	0.072 (3)	0.120 (4)	−0.035 (3)	0.003 (4)	0.001 (3)
F3	0.101 (4)	0.104 (4)	0.121 (4)	−0.014 (3)	0.050 (3)	0.031 (3)
F4	0.153 (5)	0.098 (4)	0.072 (3)	−0.016 (3)	0.067 (3)	−0.003 (3)
O1	0.091 (4)	0.056 (3)	0.054 (3)	0.013 (3)	0.030 (3)	0.017 (2)
O2	0.109 (4)	0.075 (3)	0.079 (4)	0.024 (3)	0.048 (3)	0.011 (3)
O3	0.082 (4)	0.073 (3)	0.064 (3)	−0.010 (3)	0.027 (3)	−0.009 (3)
O4	0.101 (4)	0.067 (3)	0.063 (3)	−0.008 (3)	0.035 (3)	−0.017 (2)
C1	0.099 (3)	0.065 (3)	0.052 (2)	0.002 (3)	0.030 (2)	0.004 (2)
C2	0.090 (3)	0.052 (3)	0.047 (3)	0.002 (3)	0.018 (3)	0.007 (2)
C3	0.096 (3)	0.056 (3)	0.055 (3)	−0.001 (3)	0.016 (3)	0.002 (3)
C4	0.093 (4)	0.057 (3)	0.063 (3)	−0.004 (3)	0.009 (3)	0.009 (3)
C5	0.089 (4)	0.060 (3)	0.065 (3)	−0.004 (3)	0.022 (3)	0.012 (3)
C6	0.091 (4)	0.064 (3)	0.054 (3)	−0.003 (3)	0.025 (3)	0.007 (3)
C7	0.086 (3)	0.051 (3)	0.043 (3)	0.000 (3)	0.019 (3)	0.005 (2)
C8	0.093 (3)	0.056 (3)	0.050 (3)	0.001 (3)	0.025 (3)	0.001 (3)
C9	0.112 (4)	0.094 (4)	0.089 (4)	0.010 (4)	0.027 (4)	0.013 (4)
C10	0.133 (5)	0.111 (5)	0.114 (5)	0.005 (4)	0.021 (4)	0.010 (4)
C11	0.146 (6)	0.131 (6)	0.130 (6)	0.008 (5)	0.020 (5)	0.006 (5)
C12	0.148 (10)	0.191 (11)	0.184 (11)	0.031 (9)	0.021 (10)	0.000 (9)
C13	0.116 (4)	0.087 (4)	0.071 (3)	0.008 (4)	0.036 (3)	0.004 (3)
C14	0.119 (4)	0.085 (4)	0.063 (3)	−0.001 (4)	0.023 (3)	0.005 (3)
C15	0.128 (5)	0.109 (5)	0.074 (4)	0.002 (4)	0.027 (4)	−0.001 (4)
C16	0.150 (8)	0.149 (7)	0.105 (7)	−0.014 (7)	0.009 (6)	0.005 (6)

Geometric parameters (Å, º)

Sn1—C9	2.061 (11)	C9—H9A	0.9700
Sn1—O1	2.075 (5)	C9—H9B	0.9700
Sn1—O4^i	2.100 (6)	C10—C11	1.506 (14)
Sn1—C13	2.117 (9)	C10—H10A	0.9700
Sn1—O2	2.690 (5)	C10—H10B	0.9700
F1—C3	1.337 (9)	C11—C12	1.553 (15)
F2—C4	1.335 (9)	C11—H11A	0.9700
F3—C5	1.343 (9)	C11—H11B	0.9700
F4—C6	1.335 (9)	C12—H12A	0.9600
O1—C1	1.308 (9)	C12—H12B	0.9600
O2—C1	1.204 (10)	C12—H12C	0.9600
O3—C8	1.219 (10)	C13—C14	1.541 (11)
O4—C8	1.290 (10)	C13—H13A	0.9700
O4—Sn1^ii	2.100 (6)	C13—H13B	0.9700
C1—C2	1.506 (11)	C14—C15	1.470 (11)
C2—C3	1.369 (11)	C14—H14A	0.9700
C2—C7	1.393 (10)	C14—H14B	0.9700
C3—C4	1.377 (12)	C15—C16	1.543 (12)
C4—C5	1.365 (12)	C15—H15A	0.9700
C5—C6	1.352 (11)	C15—H15B	0.9700
C6—C7	1.370 (10)	C16—H16A	0.9600
C7—C8	1.510 (11)	C16—H16B	0.9600
C9—C10	1.589 (13)	C16—H16C	0.9600
C9—Sn1—O1	103.5 (3)	C11—C10—C9	107.1 (10)
C9—Sn1—O4^i	106.7 (3)	C11—C10—H10A	110.3
O1—Sn1—O4^i	83.2 (2)	C9—C10—H10A	110.3
C9—Sn1—C13	136.4 (4)	C11—C10—H10B	110.3
O1—Sn1—C13	108.8 (3)	C9—C10—H10B	110.3
O4^i—Sn1—C13	105.6 (3)	H10A—C10—H10B	108.6
C9—Sn1—O2	86.8 (3)	C10—C11—C12	107.5 (12)
O1—Sn1—O2	53.40 (19)	C10—C11—H11A	110.2
O4^i—Sn1—O2	136.6 (2)	C12—C11—H11A	110.2
C13—Sn1—O2	89.4 (3)	C10—C11—H11B	110.2
C1—O1—Sn1	104.7 (5)	C12—C11—H11B	110.2
C1—O2—Sn1	78.6 (4)	H11A—C11—H11B	108.5
C8—O4—Sn1^ii	103.5 (6)	C11—C12—H12A	109.5
O2—C1—O1	123.2 (7)	C11—C12—H12B	109.5
O2—C1—C2	123.2 (7)	H12A—C12—H12B	109.5
O1—C1—C2	113.5 (7)	C11—C12—H12C	109.5
C3—C2—C7	118.2 (7)	H12A—C12—H12C	109.5
C3—C2—C1	118.4 (7)	H12B—C12—H12C	109.5
C7—C2—C1	123.1 (7)	C14—C13—Sn1	115.1 (6)
F1—C3—C2	120.5 (7)	C14—C13—H13A	108.5
F1—C3—C4	118.1 (7)	Sn1—C13—H13A	108.5
C2—C3—C4	121.4 (7)	C14—C13—H13B	108.5
F2—C4—C5	120.4 (8)	Sn1—C13—H13B	108.5
F2—C4—C3	120.0 (8)	H13A—C13—H13B	107.5
C5—C4—C3	119.6 (8)	C15—C14—C13	112.4 (8)
F3—C5—C6	121.4 (8)	C15—C14—H14A	109.1
F3—C5—C4	118.9 (8)	C13—C14—H14A	109.1
C6—C5—C4	119.7 (8)	C15—C14—H14B	109.1
F4—C6—C5	117.1 (7)	C13—C14—H14B	109.1
F4—C6—C7	121.3 (7)	H14A—C14—H14B	107.9
C5—C6—C7	121.6 (7)	C14—C15—C16	112.7 (9)
C6—C7—C2	119.4 (7)	C14—C15—H15A	109.1
C6—C7—C8	122.2 (7)	C16—C15—H15A	109.1
C2—C7—C8	118.3 (7)	C14—C15—H15B	109.1
O3—C8—O4	122.3 (7)	C16—C15—H15B	109.1
O3—C8—C7	121.7 (7)	H15A—C15—H15B	107.8
O4—C8—C7	116.0 (8)	C15—C16—H16A	109.5
C10—C9—Sn1	99.4 (7)	C15—C16—H16B	109.5
C10—C9—H9A	111.9	H16A—C16—H16B	109.5
Sn1—C9—H9A	111.9	C15—C16—H16C	109.5
C10—C9—H9B	111.9	H16A—C16—H16C	109.5
Sn1—C9—H9B	111.9	H16B—C16—H16C	109.5
H9A—C9—H9B	109.6

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