Tetra­kis(2,4,5-trichloro­phen­yl)stannane

Shaikh, N.S.; Parkin, S.; Lehmler, H.-J.

doi:10.1107/S1600536807020909

Tetrakis(2,4,5-trichlorophenyl)stannane

N. S. Shaikh, S. Parkin and H.-J. Lehmler

The molecule of the title compound, [Sn(C₆H₂Cl₃)₄], occupies a general position in the crystal structure, but shows an approximate $\overline{4}$ molecular symmetry.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807020909/ya2050sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807020909/ya2050Isup2.hkl Contains datablock I

CCDC reference: 650506

checkCIF report

Key indicators

Single-crystal X-ray study
T = 90 K
Mean (C-C) = 0.004 Å
R factor = 0.024
wR factor = 0.059
Data-to-parameter ratio = 15.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT432_ALERT_2_C Short Inter X...Y Contact  Cl9    ..  C15     ..       3.23 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

Data collection: APEX2 (Bruker–Nonius, 2004); cell refinement: APEX2; data reduction: APEX2; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.

Tetrakis(2,4,5-trichlorophenyl)stannane top

Crystal data top

[Sn(C₆H₂Cl₃)₄]	F(000) = 1624
M_r = 840.39	D_x = 1.954 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 528 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 7.9536 (4) Å	Cell parameters from 9423 reflections
b = 33.8974 (15) Å	θ = 2.6–68.2°
c = 11.2442 (5) Å	µ = 17.60 mm⁻¹
β = 109.584 (2)°	T = 90 K
V = 2856.1 (2) Å³	Block, colourless
Z = 4	0.08 × 0.08 × 0.04 mm

Data collection top

Bruker X8 Proteum diffractometer	5021 independent reflections
Radiation source: fine-focus rotating anode	4856 reflections with I > 2σ(I)
Bruker Helios multilayer optics monochromator	R_int = 0.040
Detector resolution: 18 pixels mm^-1	θ_max = 68.0°, θ_min = 2.6°
ω and φ scans	h = −9→8
Absorption correction: multi-scan (SADABS in APEX2; Bruker–Nonius, 2004)	k = −39→40
T_min = 0.328, T_max = 0.543	l = −13→13
27165 measured reflections

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)] = 0.024	H-atom parameters constrained
wR(F²) = 0.059	w = 1/[σ²(F_o²) + (0.023P)² + 4.3091P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.006
5021 reflections	Δρ_max = 0.65 e Å⁻³
335 parameters	Δρ_min = −0.55 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00008 (2)

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Sn1	0.36707 (2)	0.123116 (4)	0.177113 (14)	0.01026 (7)
Cl1	−0.00087 (8)	0.081837 (19)	−0.02428 (5)	0.01808 (14)
Cl2	−0.06451 (9)	−0.034514 (18)	0.27688 (6)	0.01902 (14)
Cl3	0.27150 (9)	−0.002726 (19)	0.49316 (6)	0.01951 (14)
Cl4	0.71508 (9)	0.061791 (17)	0.27464 (6)	0.01671 (14)
Cl5	1.08971 (9)	0.14191 (2)	0.68649 (6)	0.02259 (15)
Cl6	0.81176 (10)	0.21200 (2)	0.60452 (7)	0.02861 (17)
Cl7	0.22906 (8)	0.151585 (18)	0.41483 (6)	0.01692 (14)
Cl8	−0.21483 (9)	0.26507 (2)	0.16692 (7)	0.02627 (17)
Cl9	−0.14046 (9)	0.241891 (19)	−0.08343 (6)	0.02319 (15)
Cl10	0.49072 (9)	0.194396 (18)	0.00694 (6)	0.01957 (14)
Cl11	0.62846 (10)	0.09580 (2)	−0.32006 (6)	0.02532 (16)
Cl12	0.53942 (9)	0.023495 (18)	−0.17460 (6)	0.01944 (14)
C1	0.2393 (3)	0.07031 (7)	0.2088 (2)	0.0122 (5)
C2	0.0860 (4)	0.05674 (8)	0.1179 (2)	0.0136 (5)
C3	−0.0061 (4)	0.02411 (8)	0.1363 (2)	0.0148 (5)
H3	−0.1087	0.0149	0.0709	0.018*
C4	0.0542 (3)	0.00508 (7)	0.2518 (2)	0.0133 (5)
C5	0.2036 (4)	0.01894 (8)	0.3465 (2)	0.0138 (5)
C6	0.2962 (3)	0.05099 (7)	0.3243 (2)	0.0134 (5)
H6	0.4003	0.0599	0.3890	0.016*
C7	0.6082 (3)	0.13261 (8)	0.3329 (2)	0.0132 (5)
C8	0.7369 (3)	0.10349 (7)	0.3678 (2)	0.0125 (5)
C9	0.8855 (4)	0.10598 (8)	0.4755 (2)	0.0157 (5)
H9	0.9704	0.0852	0.4980	0.019*
C10	0.9079 (4)	0.13934 (8)	0.5497 (2)	0.0161 (6)
C11	0.7854 (4)	0.16975 (8)	0.5145 (2)	0.0160 (5)
C12	0.6363 (4)	0.16636 (8)	0.4074 (2)	0.0154 (5)
H12	0.5521	0.1873	0.3844	0.018*
C13	0.1773 (3)	0.16859 (7)	0.1697 (2)	0.0129 (5)
C14	0.1303 (3)	0.17726 (7)	0.2745 (2)	0.0137 (5)
C15	0.0083 (4)	0.20623 (8)	0.2747 (3)	0.0165 (6)
H15	−0.0198	0.2117	0.3488	0.020*
C16	−0.0720 (4)	0.22712 (8)	0.1648 (3)	0.0180 (6)
C17	−0.0348 (4)	0.21781 (7)	0.0564 (3)	0.0166 (6)
C18	0.0898 (4)	0.18903 (8)	0.0592 (2)	0.0150 (5)
H18	0.1158	0.1832	−0.0154	0.018*
C19	0.4374 (3)	0.11573 (8)	0.0103 (2)	0.0121 (5)
C20	0.4901 (3)	0.14648 (7)	−0.0493 (2)	0.0140 (5)
C21	0.5464 (4)	0.14110 (8)	−0.1520 (2)	0.0163 (5)
H21	0.5773	0.1630	−0.1930	0.020*
C22	0.5568 (4)	0.10309 (8)	−0.1935 (2)	0.0159 (5)
C23	0.5123 (3)	0.07137 (7)	−0.1317 (2)	0.0135 (5)
C24	0.4499 (3)	0.07780 (8)	−0.0332 (2)	0.0133 (5)
H24	0.4148	0.0559	0.0060	0.016*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01102 (11)	0.01061 (10)	0.00803 (10)	0.00094 (6)	0.00173 (7)	−0.00033 (5)
Cl1	0.0169 (3)	0.0227 (3)	0.0102 (3)	−0.0010 (2)	−0.0014 (2)	0.0026 (2)
Cl2	0.0190 (3)	0.0181 (3)	0.0204 (3)	−0.0052 (2)	0.0072 (3)	−0.0007 (2)
Cl3	0.0210 (4)	0.0227 (3)	0.0131 (3)	−0.0014 (2)	0.0034 (2)	0.0057 (2)
Cl4	0.0193 (3)	0.0155 (3)	0.0134 (3)	0.0051 (2)	0.0030 (2)	−0.0015 (2)
Cl5	0.0176 (3)	0.0279 (3)	0.0151 (3)	−0.0059 (3)	−0.0041 (2)	0.0013 (2)
Cl6	0.0250 (4)	0.0259 (4)	0.0284 (4)	−0.0036 (3)	0.0002 (3)	−0.0158 (3)
Cl7	0.0178 (3)	0.0214 (3)	0.0122 (3)	−0.0005 (2)	0.0057 (2)	0.0009 (2)
Cl8	0.0200 (4)	0.0209 (3)	0.0323 (4)	0.0078 (3)	0.0013 (3)	−0.0103 (3)
Cl9	0.0215 (4)	0.0199 (3)	0.0227 (3)	0.0055 (3)	0.0001 (3)	0.0064 (2)
Cl10	0.0236 (4)	0.0129 (3)	0.0237 (3)	−0.0025 (2)	0.0099 (3)	−0.0011 (2)
Cl11	0.0290 (4)	0.0355 (4)	0.0167 (3)	0.0007 (3)	0.0146 (3)	−0.0007 (3)
Cl12	0.0205 (3)	0.0193 (3)	0.0188 (3)	0.0005 (2)	0.0069 (3)	−0.0075 (2)
C1	0.0137 (14)	0.0110 (12)	0.0130 (12)	0.0002 (9)	0.0060 (10)	−0.0004 (9)
C2	0.0130 (13)	0.0160 (12)	0.0107 (12)	0.0033 (10)	0.0025 (10)	−0.0008 (9)
C3	0.0139 (14)	0.0182 (13)	0.0112 (12)	0.0010 (10)	0.0027 (10)	−0.0035 (10)
C4	0.0124 (13)	0.0125 (12)	0.0174 (13)	0.0003 (9)	0.0084 (10)	−0.0031 (10)
C5	0.0149 (14)	0.0157 (13)	0.0109 (12)	0.0039 (10)	0.0046 (10)	0.0017 (9)
C6	0.0136 (13)	0.0145 (12)	0.0110 (12)	0.0020 (10)	0.0025 (10)	−0.0021 (9)
C7	0.0123 (13)	0.0161 (12)	0.0102 (12)	−0.0027 (10)	0.0024 (10)	0.0003 (9)
C8	0.0136 (13)	0.0143 (12)	0.0107 (12)	−0.0025 (10)	0.0054 (10)	−0.0006 (9)
C9	0.0147 (14)	0.0154 (13)	0.0174 (13)	0.0006 (10)	0.0061 (11)	0.0039 (10)
C10	0.0114 (14)	0.0226 (14)	0.0118 (12)	−0.0062 (10)	0.0003 (10)	0.0010 (10)
C11	0.0164 (14)	0.0167 (13)	0.0149 (13)	−0.0061 (10)	0.0053 (10)	−0.0041 (10)
C12	0.0151 (14)	0.0150 (13)	0.0159 (13)	−0.0008 (10)	0.0050 (10)	−0.0002 (10)
C13	0.0110 (13)	0.0119 (12)	0.0146 (12)	0.0007 (9)	0.0027 (10)	−0.0024 (9)
C14	0.0125 (13)	0.0135 (12)	0.0134 (12)	−0.0029 (10)	0.0020 (10)	−0.0008 (9)
C15	0.0116 (14)	0.0194 (13)	0.0178 (13)	−0.0018 (10)	0.0040 (10)	−0.0059 (10)
C16	0.0108 (14)	0.0139 (13)	0.0259 (15)	0.0000 (10)	0.0016 (11)	−0.0050 (10)
C17	0.0142 (14)	0.0130 (12)	0.0188 (13)	0.0009 (10)	0.0005 (11)	0.0000 (10)
C18	0.0151 (14)	0.0150 (13)	0.0140 (12)	0.0003 (10)	0.0036 (10)	−0.0021 (10)
C19	0.0113 (13)	0.0172 (12)	0.0073 (11)	0.0009 (10)	0.0025 (9)	−0.0012 (9)
C20	0.0125 (14)	0.0134 (12)	0.0138 (12)	0.0002 (10)	0.0014 (10)	0.0016 (9)
C21	0.0139 (14)	0.0197 (13)	0.0146 (13)	−0.0005 (10)	0.0038 (10)	0.0050 (10)
C22	0.0131 (14)	0.0261 (14)	0.0077 (12)	0.0005 (10)	0.0023 (10)	−0.0009 (10)
C23	0.0119 (13)	0.0154 (13)	0.0103 (12)	−0.0001 (10)	−0.0003 (10)	−0.0047 (9)
C24	0.0112 (13)	0.0162 (12)	0.0106 (12)	−0.0010 (10)	0.0010 (10)	0.0001 (9)

Geometric parameters (Å, º) top

Sn1—C13	2.139 (3)	C7—C8	1.381 (4)
Sn1—C7	2.144 (2)	C7—C12	1.391 (4)
Sn1—C19	2.144 (3)	C8—C9	1.383 (4)
Sn1—C1	2.146 (3)	C9—C10	1.381 (4)
Cl1—C2	1.737 (3)	C9—H9	0.9500
Cl2—C4	1.717 (3)	C10—C11	1.382 (4)
Cl3—C5	1.719 (3)	C11—C12	1.383 (4)
Cl4—C8	1.733 (3)	C12—H12	0.9500
Cl5—C10	1.724 (3)	C13—C14	1.383 (4)
Cl6—C11	1.726 (3)	C13—C18	1.389 (4)
Cl7—C14	1.741 (3)	C14—C15	1.381 (4)
Cl8—C16	1.722 (3)	C15—C16	1.382 (4)
Cl9—C17	1.720 (3)	C15—H15	0.9500
Cl10—C20	1.742 (3)	C16—C17	1.383 (4)
Cl11—C22	1.719 (3)	C17—C18	1.383 (4)
Cl12—C23	1.727 (3)	C18—H18	0.9500
C1—C2	1.381 (4)	C19—C20	1.378 (4)
C1—C6	1.388 (4)	C19—C24	1.391 (4)
C2—C3	1.379 (4)	C20—C21	1.384 (4)
C3—C4	1.385 (4)	C21—C22	1.382 (4)
C3—H3	0.9500	C21—H21	0.9500
C4—C5	1.385 (4)	C22—C23	1.389 (4)
C5—C6	1.381 (4)	C23—C24	1.374 (4)
C6—H6	0.9500	C24—H24	0.9500

C13—Sn1—C7	110.47 (10)	C11—C12—C7	120.7 (2)
C13—Sn1—C19	115.94 (10)	C11—C12—H12	119.6
C7—Sn1—C19	107.94 (10)	C7—C12—H12	119.6
C13—Sn1—C1	103.90 (10)	C14—C13—C18	117.3 (2)
C7—Sn1—C1	109.47 (10)	C14—C13—Sn1	120.59 (18)
C19—Sn1—C1	108.96 (10)	C18—C13—Sn1	122.02 (19)
C2—C1—C6	117.8 (2)	C15—C14—C13	122.9 (2)
C2—C1—Sn1	120.31 (18)	C15—C14—Cl7	117.3 (2)
C6—C1—Sn1	121.64 (18)	C13—C14—Cl7	119.8 (2)
C3—C2—C1	122.5 (2)	C14—C15—C16	118.5 (3)
C3—C2—Cl1	117.60 (19)	C14—C15—H15	120.7
C1—C2—Cl1	119.9 (2)	C16—C15—H15	120.7
C2—C3—C4	118.7 (2)	C15—C16—C17	120.0 (2)
C2—C3—H3	120.7	C15—C16—Cl8	118.7 (2)
C4—C3—H3	120.7	C17—C16—Cl8	121.3 (2)
C3—C4—C5	120.1 (2)	C18—C17—C16	120.2 (2)
C3—C4—Cl2	118.8 (2)	C18—C17—Cl9	118.8 (2)
C5—C4—Cl2	121.1 (2)	C16—C17—Cl9	120.9 (2)
C6—C5—C4	120.0 (2)	C17—C18—C13	120.9 (3)
C6—C5—Cl3	119.6 (2)	C17—C18—H18	119.6
C4—C5—Cl3	120.3 (2)	C13—C18—H18	119.6
C5—C6—C1	120.9 (2)	C20—C19—C24	117.4 (2)
C5—C6—H6	119.6	C20—C19—Sn1	123.22 (19)
C1—C6—H6	119.6	C24—C19—Sn1	119.04 (19)
C8—C7—C12	117.5 (2)	C19—C20—C21	122.8 (2)
C8—C7—Sn1	119.98 (19)	C19—C20—Cl10	119.6 (2)
C12—C7—Sn1	122.3 (2)	C21—C20—Cl10	117.6 (2)
C7—C8—C9	122.7 (2)	C22—C21—C20	118.5 (2)
C7—C8—Cl4	119.78 (19)	C22—C21—H21	120.7
C9—C8—Cl4	117.5 (2)	C20—C21—H21	120.7
C10—C9—C8	118.6 (2)	C21—C22—C23	119.9 (2)
C10—C9—H9	120.7	C21—C22—Cl11	119.2 (2)
C8—C9—H9	120.7	C23—C22—Cl11	120.9 (2)
C9—C10—C11	120.1 (2)	C24—C23—C22	120.1 (2)
C9—C10—Cl5	118.7 (2)	C24—C23—Cl12	119.1 (2)
C11—C10—Cl5	121.2 (2)	C22—C23—Cl12	120.7 (2)
C10—C11—C12	120.3 (2)	C23—C24—C19	121.2 (2)
C10—C11—Cl6	121.0 (2)	C23—C24—H24	119.4
C12—C11—Cl6	118.7 (2)	C19—C24—H24	119.4

C13—Sn1—C1—C2	65.6 (2)	C7—Sn1—C13—C14	−53.2 (2)
C7—Sn1—C1—C2	−176.4 (2)	C19—Sn1—C13—C14	−176.42 (19)
C19—Sn1—C1—C2	−58.6 (2)	C1—Sn1—C13—C14	64.1 (2)
C13—Sn1—C1—C6	−108.0 (2)	C7—Sn1—C13—C18	130.3 (2)
C7—Sn1—C1—C6	10.0 (2)	C19—Sn1—C13—C18	7.1 (2)
C19—Sn1—C1—C6	127.8 (2)	C1—Sn1—C13—C18	−112.4 (2)
C6—C1—C2—C3	−2.8 (4)	C18—C13—C14—C15	−3.2 (4)
Sn1—C1—C2—C3	−176.7 (2)	Sn1—C13—C14—C15	−179.8 (2)
C6—C1—C2—Cl1	175.4 (2)	C18—C13—C14—Cl7	177.81 (19)
Sn1—C1—C2—Cl1	1.5 (3)	Sn1—C13—C14—Cl7	1.2 (3)
C1—C2—C3—C4	2.3 (4)	C13—C14—C15—C16	0.9 (4)
Cl1—C2—C3—C4	−176.0 (2)	Cl7—C14—C15—C16	179.9 (2)
C2—C3—C4—C5	0.3 (4)	C14—C15—C16—C17	2.5 (4)
C2—C3—C4—Cl2	177.8 (2)	C14—C15—C16—Cl8	−176.5 (2)
C3—C4—C5—C6	−2.1 (4)	C15—C16—C17—C18	−3.5 (4)
Cl2—C4—C5—C6	−179.6 (2)	Cl8—C16—C17—C18	175.5 (2)
C3—C4—C5—Cl3	176.2 (2)	C15—C16—C17—Cl9	177.1 (2)
Cl2—C4—C5—Cl3	−1.3 (3)	Cl8—C16—C17—Cl9	−3.9 (3)
C4—C5—C6—C1	1.6 (4)	C16—C17—C18—C13	1.1 (4)
Cl3—C5—C6—C1	−176.7 (2)	Cl9—C17—C18—C13	−179.5 (2)
C2—C1—C6—C5	0.9 (4)	C14—C13—C18—C17	2.2 (4)
Sn1—C1—C6—C5	174.63 (19)	Sn1—C13—C18—C17	178.78 (19)
C13—Sn1—C7—C8	169.3 (2)	C13—Sn1—C19—C20	50.5 (2)
C19—Sn1—C7—C8	−63.0 (2)	C7—Sn1—C19—C20	−74.0 (2)
C1—Sn1—C7—C8	55.5 (2)	C1—Sn1—C19—C20	167.2 (2)
C13—Sn1—C7—C12	−6.1 (3)	C13—Sn1—C19—C24	−136.77 (19)
C19—Sn1—C7—C12	121.6 (2)	C7—Sn1—C19—C24	98.7 (2)
C1—Sn1—C7—C12	−119.9 (2)	C1—Sn1—C19—C24	−20.1 (2)
C12—C7—C8—C9	3.0 (4)	C24—C19—C20—C21	2.8 (4)
Sn1—C7—C8—C9	−172.6 (2)	Sn1—C19—C20—C21	175.62 (19)
C12—C7—C8—Cl4	−176.9 (2)	C24—C19—C20—Cl10	−176.03 (19)
Sn1—C7—C8—Cl4	7.5 (3)	Sn1—C19—C20—Cl10	−3.2 (3)
C7—C8—C9—C10	−1.4 (4)	C19—C20—C21—C22	−2.5 (4)
Cl4—C8—C9—C10	178.5 (2)	Cl10—C20—C21—C22	176.3 (2)
C8—C9—C10—C11	−1.4 (4)	C20—C21—C22—C23	−0.4 (4)
C8—C9—C10—Cl5	178.1 (2)	C20—C21—C22—Cl11	−179.4 (2)
C9—C10—C11—C12	2.4 (4)	C21—C22—C23—C24	3.0 (4)
Cl5—C10—C11—C12	−177.1 (2)	Cl11—C22—C23—C24	−178.0 (2)
C9—C10—C11—Cl6	−179.2 (2)	C21—C22—C23—Cl12	−175.3 (2)
Cl5—C10—C11—Cl6	1.3 (3)	Cl11—C22—C23—Cl12	3.7 (3)
C10—C11—C12—C7	−0.7 (4)	C22—C23—C24—C19	−2.8 (4)
Cl6—C11—C12—C7	−179.1 (2)	Cl12—C23—C24—C19	175.6 (2)
C8—C7—C12—C11	−2.0 (4)	C20—C19—C24—C23	−0.1 (4)
Sn1—C7—C12—C11	173.5 (2)	Sn1—C19—C24—C23	−173.21 (19)

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Tetra­kis(2,4,5-trichloro­phen­yl)stannane

Supporting information

Key indicators

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Tetrakis(2,4,5-trichlorophenyl)stannane