A hexa­gonal modification of catena-poly[[ethyl­diphenyl­tin(IV)]-μ-2-chloro­acetato-κ²O:O′]

In the title coordination polymer, [Sn(C₂H₅)(C₆H₅)₂(C₂H₂ClO₂)]_n, the five-coordinate Sn atom shows an SnC₃O₂ trigonal–bipyramidal geometry, with O atoms in the axial positions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.012 Å
• R factor = 0.040
• wR factor = 0.114
• Data-to-parameter ratio = 19.5

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT601_ALERT_2_A Structure Contains Solvent Accessible VOIDS of .     212.00 A   3 

Author Response: There are no atoms in the voids.

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       3.51
PLAT141_ALERT_4_C su on a - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.82 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.45
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         12

Alert level G
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               3055
           Count of symmetry unique reflns         1566
           Completeness (_total/calc)            195.08%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1489
           Fraction of Friedel pairs measured     0.951
           Are heavy atom types Z>Si present        yes

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

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   4 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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Computing details

Data collection: APEXII (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: SHELXL97.

catena-poly[[ethyldiphenyltin(IV)]-µ-2-chloroacetato-κ²O:O']

Crystal data

[Sn(C2H5)(C6H5)2(C2H2ClO2)]	Dx = 1.506 Mg m^−3
Mr = 395.44	Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P61	Cell parameters from 9083 reflections
Hall symbol: P 61	θ = 2.3–30.2°
a = 10.8105 (1) Å	µ = 1.62 mm^−1
c = 25.8402 (3) Å	T = 173 K
V = 2615.28 (4) Å^3	Block, colorless
Z = 6	0.20 × 0.17 × 0.03 mm
F(000) = 1176

Data collection

Bruker APEXII CCD diffractometer	3055 independent reflections
Radiation source: medium-focus sealed tube	2882 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.037
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.685, Tmax = 0.953	k = −12→12
34368 measured reflections	l = −30→30

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)] = 0.040	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0801P)^2 + 4.0181P] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
3055 reflections	Δρmax = 2.07 e Å^−3
157 parameters	Δρmin = −0.59 e Å^−3
2 restraints	Absolute structure: Flack (1983), with 1491 reflections
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.02 (5)

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

	x	y	z	Uiso*/Ueq
Sn1	0.66134 (4)	1.06225 (5)	0.691650 (19)	0.03286 (16)
Cl1	0.5507 (2)	1.3340 (2)	0.56975 (7)	0.0518 (5)
O1	0.6883 (6)	1.2251 (6)	0.63484 (18)	0.0419 (12)
O2	0.8787 (5)	1.2760 (5)	0.58624 (18)	0.0362 (11)
C1	0.6084 (6)	0.9093 (6)	0.63104 (16)	0.0456 (19)
C2	0.5283 (6)	0.9093 (5)	0.58898 (18)	0.0424 (16)
H2	0.5020	0.9807	0.5862	0.051*
C3	0.4868 (6)	0.8049 (7)	0.55101 (18)	0.057 (2)
H3	0.4320	0.8049	0.5223	0.069*
C4	0.5253 (8)	0.7004 (6)	0.5551 (2)	0.087 (3)
H4	0.4969	0.6290	0.5292	0.104*
C5	0.6055 (9)	0.7003 (7)	0.5972 (3)	0.093 (4)
H5	0.6318	0.6289	0.6000	0.112*
C6	0.6470 (7)	0.8048 (8)	0.6351 (2)	0.074 (3)
H6	0.7018	0.8048	0.6639	0.089*
C7	0.4956 (4)	1.0872 (6)	0.72441 (14)	0.0335 (14)
C8	0.3993 (5)	1.1013 (7)	0.69280 (12)	0.0498 (19)
H8	0.4082	1.1007	0.6562	0.060*
C9	0.2901 (5)	1.1163 (8)	0.71469 (17)	0.065 (3)
H9	0.2243	1.1259	0.6931	0.078*
C10	0.2771 (5)	1.1172 (7)	0.76819 (18)	0.061 (2)
H10	0.2025	1.1274	0.7831	0.073*
C11	0.3734 (5)	1.1031 (7)	0.79980 (12)	0.051 (2)
H11	0.3646	1.1038	0.8364	0.061*
C12	0.4827 (5)	1.0881 (6)	0.77791 (13)	0.0408 (16)
H12	0.5485	1.0785	0.7995	0.049*
C13	0.8699 (8)	1.1793 (11)	0.7246 (3)	0.060 (2)
H13A	0.9140	1.1181	0.7251	0.072*
H13B	0.9300	1.2633	0.7026	0.072*
C14	0.8666 (10)	1.2300 (11)	0.7802 (3)	0.075 (3)
H14A	0.9642	1.2838	0.7937	0.113*
H14B	0.8095	1.1469	0.8023	0.113*
H14C	0.8239	1.2914	0.7798	0.113*
C15	0.7679 (7)	1.2802 (7)	0.5960 (2)	0.0338 (15)
C16	0.7243 (9)	1.3631 (10)	0.5591 (3)	0.052 (2)
H16A	0.7307	1.3357	0.5231	0.062*
H16B	0.7933	1.4665	0.5628	0.062*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.0284 (2)	0.0523 (3)	0.0177 (2)	0.0200 (2)	0.00224 (17)	0.01026 (19)
Cl1	0.0636 (12)	0.0788 (14)	0.0304 (9)	0.0485 (11)	0.0084 (8)	0.0152 (9)
O1	0.048 (3)	0.057 (3)	0.021 (2)	0.027 (2)	0.007 (2)	0.012 (2)
O2	0.046 (3)	0.038 (3)	0.029 (3)	0.024 (2)	0.008 (2)	0.008 (2)
C1	0.066 (5)	0.061 (5)	0.027 (4)	0.045 (4)	0.024 (3)	0.019 (3)
C2	0.039 (4)	0.052 (4)	0.031 (4)	0.019 (3)	0.005 (3)	−0.001 (3)
C3	0.062 (5)	0.079 (6)	0.034 (4)	0.038 (5)	−0.003 (4)	−0.003 (4)
C4	0.108 (9)	0.078 (7)	0.072 (8)	0.045 (7)	0.011 (7)	−0.019 (6)
C5	0.146 (12)	0.113 (10)	0.066 (8)	0.098 (10)	0.009 (7)	0.000 (7)
C6	0.115 (9)	0.119 (9)	0.033 (4)	0.093 (8)	0.014 (5)	0.009 (5)
C7	0.032 (3)	0.044 (4)	0.024 (3)	0.019 (3)	0.003 (2)	0.007 (3)
C8	0.040 (3)	0.096 (6)	0.014 (3)	0.034 (4)	0.002 (3)	0.008 (4)
C9	0.054 (5)	0.130 (9)	0.032 (4)	0.062 (6)	−0.004 (4)	0.002 (5)
C10	0.042 (4)	0.105 (7)	0.037 (4)	0.039 (5)	−0.002 (4)	−0.008 (5)
C11	0.057 (5)	0.085 (6)	0.020 (3)	0.043 (5)	0.006 (3)	0.000 (4)
C12	0.042 (4)	0.053 (4)	0.025 (3)	0.022 (3)	−0.009 (3)	0.001 (3)
C13	0.032 (4)	0.094 (7)	0.044 (5)	0.023 (4)	0.000 (3)	0.027 (4)
C14	0.046 (5)	0.086 (7)	0.045 (5)	−0.003 (5)	−0.015 (4)	0.021 (5)
C15	0.043 (4)	0.032 (3)	0.015 (3)	0.010 (3)	0.003 (3)	0.004 (2)
C16	0.049 (4)	0.078 (6)	0.039 (4)	0.040 (4)	0.012 (3)	0.026 (4)

Geometric parameters (Å, º)

Sn1—C1	2.137 (4)	C7—C8	1.3900
Sn1—C7	2.117 (3)	C7—C12	1.3900
Sn1—C13	2.135 (8)	C8—C9	1.3900
Sn1—O1	2.197 (5)	C8—H8	0.9500
Sn1—O2^i	2.364 (5)	C9—C10	1.3900
Cl1—C16	1.762 (8)	C9—H9	0.9500
O1—C15	1.262 (8)	C10—C11	1.3900
O2—C15	1.247 (9)	C10—H10	0.9500
O2—Sn1^ii	2.364 (5)	C11—C12	1.3900
C1—C2	1.3900	C11—H11	0.9500
C1—C6	1.3900	C12—H12	0.9500
C2—C3	1.3900	C13—C14	1.544 (8)
C2—H2	0.9500	C13—H13A	0.9900
C3—C4	1.3900	C13—H13B	0.9900
C3—H3	0.9500	C14—H14A	0.9800
C4—C5	1.3900	C14—H14B	0.9800
C4—H4	0.9500	C14—H14C	0.9800
C5—C6	1.3900	C15—C16	1.534 (10)
C5—H5	0.9500	C16—H16A	0.9900
C6—H6	0.9500	C16—H16B	0.9900
C1—Sn1—C7	118.4 (2)	C9—C8—H8	120.0
C1—Sn1—C13	123.0 (3)	C10—C9—C8	120.0
C1—Sn1—O1	90.4 (2)	C10—C9—H9	120.0
C1—Sn1—O2^i	89.2 (2)	C8—C9—H9	120.0
C7—Sn1—C13	118.4 (3)	C9—C10—C11	120.0
C7—Sn1—O1	87.0 (2)	C9—C10—H10	120.0
C7—Sn1—O2^i	87.2 (2)	C11—C10—H10	120.0
C13—Sn1—O1	96.5 (3)	C12—C11—C10	120.0
C13—Sn1—O2^i	89.5 (3)	C12—C11—H11	120.0
O1—Sn1—O2^i	173.06 (18)	C10—C11—H11	120.0
C15—O1—Sn1	134.2 (5)	C11—C12—C7	120.0
C15—O2—Sn1^ii	131.4 (4)	C11—C12—H12	120.0
C2—C1—C6	120.0	C7—C12—H12	120.0
C2—C1—Sn1	119.9 (3)	C14—C13—Sn1	112.1 (5)
C6—C1—Sn1	120.0 (3)	C14—C13—H13A	109.2
C3—C2—C1	120.0	Sn1—C13—H13A	109.2
C3—C2—H2	120.0	C14—C13—H13B	109.2
C1—C2—H2	120.0	Sn1—C13—H13B	109.2
C4—C3—C2	120.0	H13A—C13—H13B	107.9
C4—C3—H3	120.0	C13—C14—H14A	109.5
C2—C3—H3	120.0	C13—C14—H14B	109.5
C3—C4—C5	120.0	H14A—C14—H14B	109.5
C3—C4—H4	120.0	C13—C14—H14C	109.5
C5—C4—H4	120.0	H14A—C14—H14C	109.5
C6—C5—C4	120.0	H14B—C14—H14C	109.5
C6—C5—H5	120.0	O2—C15—O1	125.7 (6)
C4—C5—H5	120.0	O2—C15—C16	118.5 (6)
C5—C6—C1	120.0	O1—C15—C16	115.7 (6)
C5—C6—H6	120.0	C15—C16—Cl1	114.2 (5)
C1—C6—H6	120.0	C15—C16—H16A	108.7
C8—C7—C12	120.0	Cl1—C16—H16A	108.7
C8—C7—Sn1	120.4 (2)	C15—C16—H16B	108.7
C12—C7—Sn1	119.6 (2)	Cl1—C16—H16B	108.7
C7—C8—C9	120.0	H16A—C16—H16B	107.6
C7—C8—H8	120.0
C7—Sn1—O1—C15	−177.6 (7)	C13—Sn1—C7—C12	−43.5 (4)
C13—Sn1—O1—C15	64.2 (7)	C1—Sn1—C7—C12	131.9 (3)
C1—Sn1—O1—C15	−59.2 (7)	O1—Sn1—C7—C12	−139.3 (3)
C7—Sn1—C1—C2	49.9 (4)	O2^i—Sn1—C7—C12	44.4 (3)
C13—Sn1—C1—C2	−135.0 (4)	C12—C7—C8—C9	0.0
O1—Sn1—C1—C2	−36.9 (3)	Sn1—C7—C8—C9	179.4 (4)
O2^i—Sn1—C1—C2	136.2 (3)	C7—C8—C9—C10	0.0
C7—Sn1—C1—C6	−126.4 (3)	C8—C9—C10—C11	0.0
C13—Sn1—C1—C6	48.7 (4)	C9—C10—C11—C12	0.0
O1—Sn1—C1—C6	146.8 (3)	C10—C11—C12—C7	0.0
O2^i—Sn1—C1—C6	−40.1 (3)	C8—C7—C12—C11	0.0
C6—C1—C2—C3	0.0	Sn1—C7—C12—C11	−179.4 (4)
Sn1—C1—C2—C3	−176.3 (4)	C7—Sn1—C13—C14	19.7 (8)
C1—C2—C3—C4	0.0	C1—Sn1—C13—C14	−155.4 (6)
C2—C3—C4—C5	0.0	O1—Sn1—C13—C14	109.8 (7)
C3—C4—C5—C6	0.0	O2^i—Sn1—C13—C14	−66.8 (7)
C4—C5—C6—C1	0.0	Sn1^ii—O2—C15—O1	−168.3 (5)
C2—C1—C6—C5	0.0	Sn1^ii—O2—C15—C16	9.5 (10)
Sn1—C1—C6—C5	176.3 (4)	Sn1—O1—C15—O2	−17.2 (11)
C13—Sn1—C7—C8	137.1 (4)	Sn1—O1—C15—C16	164.9 (6)
C1—Sn1—C7—C8	−47.5 (4)	O2—C15—C16—Cl1	168.7 (6)
O1—Sn1—C7—C8	41.3 (3)	O1—C15—C16—Cl1	−13.3 (10)
O2^i—Sn1—C7—C8	−135.0 (3)

Symmetry codes: (i) x−y+1, x, z+1/6; (ii) y, −x+y+1, z−1/6.