Tetra­kis(4-fluoro­phen­yl)stannane

The title compound, [Sn(C₆H₄F)₄], displays significant deviation from ideal tetra­hedral mol­ecular symmetry.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.023
• wR factor = 0.061
• Data-to-parameter ratio = 13.6

checkCIF/PLATON results

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Computing details

Data collection: APEX2 (Bruker, 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: XP in SHELXTL (Sheldrick, 1994); software used to prepare material for publication: SHELX97-2 (Sheldrick, 1997) and local procedures.

Tetrakis(4-fluorophenyl)stannane

Crystal data

[Sn(C6H4F)4]	F(000) = 984
Mr = 499.06	Dx = 1.666 Mg m^−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 7000 reflections
a = 9.4775 (19) Å	θ = 4.7–67.9°
b = 19.873 (4) Å	µ = 10.61 mm^−1
c = 11.029 (2) Å	T = 90 K
β = 106.69 (3)°	Rod, colourless
V = 1989.6 (7) Å^3	0.20 × 0.06 × 0.04 mm
Z = 4

Data collection

X8 Proteum diffractometer	3582 independent reflections
Radiation source: fine-focus rotating anode	3457 reflections with I > 2σ(I)
Bruker Helios multilayer optics monochromator	Rint = 0.040
Detector resolution: 18 pixels mm^-1	θmax = 67.9°, θmin = 2.1°
ω and φ scans	h = −11→10
Absorption correction: multi-scan (SADABS in APEX2; Bruker, 2004)	k = 0→23
Tmin = 0.511, Tmax = 0.652	l = 0→13
40140 measured reflections

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)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0187P)^2 + 2.8274P] where P = (Fo^2 + 2Fc^2)/3
S = 1.14	(Δ/σ)max = 0.003
3582 reflections	Δρmax = 0.48 e Å^−3
263 parameters	Δρmin = −0.45 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: 0.0018 (2)

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
Sn1	0.370825 (16)	0.643198 (8)	0.548265 (15)	0.01463 (8)
C1	0.2684 (3)	0.73739 (12)	0.5612 (2)	0.0191 (5)
C2	0.2894 (3)	0.79098 (13)	0.4879 (2)	0.0233 (5)
H2	0.3500	0.7851	0.4334	0.028*
C3	0.2243 (3)	0.85280 (13)	0.4921 (3)	0.0301 (7)
H3	0.2395	0.8893	0.4417	0.036*
C4	0.1372 (3)	0.85993 (14)	0.5712 (3)	0.0335 (7)
C5	0.1143 (3)	0.80878 (16)	0.6464 (3)	0.0341 (7)
H5	0.0546	0.8155	0.7014	0.041*
C6	0.1796 (3)	0.74703 (14)	0.6408 (3)	0.0250 (6)
H6	0.1638	0.7109	0.6917	0.030*
C7	0.2153 (3)	0.57153 (12)	0.4460 (2)	0.0196 (5)
C8	0.0654 (3)	0.58412 (13)	0.4193 (2)	0.0214 (5)
H8	0.0331	0.6255	0.4452	0.026*
C9	−0.0379 (3)	0.53743 (14)	0.3558 (3)	0.0252 (6)
H9	−0.1404	0.5463	0.3374	0.030*
C10	0.0119 (3)	0.47814 (13)	0.3204 (3)	0.0264 (6)
C11	0.1588 (3)	0.46395 (14)	0.3418 (3)	0.0286 (6)
H11	0.1899	0.4228	0.3137	0.034*
C12	0.2601 (3)	0.51119 (14)	0.4053 (3)	0.0265 (6)
H12	0.3623	0.5022	0.4214	0.032*
C13	0.4862 (3)	0.60543 (12)	0.7305 (2)	0.0190 (5)
C14	0.4821 (3)	0.53749 (13)	0.7597 (2)	0.0212 (5)
H14	0.4182	0.5083	0.7006	0.025*
C15	0.5687 (3)	0.51166 (13)	0.8726 (3)	0.0243 (6)
H15	0.5654	0.4652	0.8917	0.029*
C16	0.6603 (3)	0.55513 (14)	0.9569 (2)	0.0237 (6)
C17	0.6677 (3)	0.62232 (14)	0.9336 (3)	0.0248 (6)
H17	0.7315	0.6511	0.9937	0.030*
C18	0.5795 (3)	0.64736 (13)	0.8198 (3)	0.0227 (6)
H18	0.5827	0.6940	0.8022	0.027*
C19	0.5311 (3)	0.66107 (12)	0.4490 (2)	0.0193 (5)
C20	0.6671 (3)	0.68909 (12)	0.5103 (2)	0.0209 (5)
H20	0.6900	0.6992	0.5980	0.025*
C21	0.7702 (3)	0.70256 (13)	0.4464 (3)	0.0231 (5)
H21	0.8631	0.7217	0.4887	0.028*
C22	0.7338 (3)	0.68733 (13)	0.3203 (3)	0.0236 (6)
C23	0.6018 (3)	0.65911 (13)	0.2551 (3)	0.0237 (5)
H23	0.5806	0.6487	0.1676	0.028*
C24	0.5001 (3)	0.64625 (12)	0.3209 (3)	0.0217 (6)
H24	0.4077	0.6270	0.2776	0.026*
F1	0.0729 (2)	0.92003 (10)	0.5760 (2)	0.0548 (6)
F2	−0.08818 (19)	0.43084 (8)	0.26296 (16)	0.0376 (4)
F3	0.74509 (19)	0.53001 (8)	1.06819 (15)	0.0332 (4)
F4	0.83216 (17)	0.70180 (9)	0.25554 (16)	0.0321 (4)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01396 (11)	0.01450 (11)	0.01457 (12)	0.00020 (6)	0.00272 (7)	−0.00048 (6)
C1	0.0173 (11)	0.0187 (12)	0.0192 (12)	0.0013 (9)	0.0020 (10)	−0.0029 (10)
C2	0.0273 (13)	0.0230 (13)	0.0179 (13)	0.0010 (10)	0.0040 (10)	−0.0007 (10)
C3	0.0369 (16)	0.0227 (14)	0.0225 (15)	0.0039 (11)	−0.0048 (12)	−0.0012 (11)
C4	0.0276 (15)	0.0271 (15)	0.0374 (18)	0.0108 (11)	−0.0042 (13)	−0.0115 (12)
C5	0.0202 (13)	0.0453 (18)	0.0379 (17)	−0.0029 (12)	0.0104 (12)	−0.0208 (15)
C6	0.0221 (13)	0.0297 (14)	0.0243 (14)	−0.0056 (11)	0.0084 (11)	−0.0063 (11)
C7	0.0219 (12)	0.0186 (12)	0.0170 (12)	0.0000 (10)	0.0036 (10)	0.0000 (10)
C8	0.0229 (13)	0.0198 (12)	0.0205 (13)	0.0018 (10)	0.0047 (10)	0.0021 (10)
C9	0.0206 (13)	0.0275 (14)	0.0237 (14)	−0.0018 (11)	0.0005 (10)	0.0039 (11)
C10	0.0300 (14)	0.0228 (13)	0.0199 (14)	−0.0076 (11)	−0.0030 (11)	0.0007 (11)
C11	0.0372 (16)	0.0216 (13)	0.0240 (14)	0.0018 (11)	0.0040 (12)	−0.0052 (11)
C12	0.0247 (13)	0.0276 (14)	0.0252 (14)	0.0034 (11)	0.0042 (11)	−0.0023 (11)
C13	0.0181 (12)	0.0205 (12)	0.0182 (12)	0.0020 (10)	0.0046 (10)	0.0008 (10)
C14	0.0232 (13)	0.0208 (12)	0.0192 (13)	−0.0023 (10)	0.0054 (10)	−0.0026 (10)
C15	0.0298 (14)	0.0186 (12)	0.0246 (14)	0.0000 (11)	0.0081 (11)	0.0023 (11)
C16	0.0247 (13)	0.0289 (14)	0.0158 (13)	0.0007 (11)	0.0028 (10)	0.0024 (10)
C17	0.0266 (13)	0.0273 (14)	0.0187 (13)	−0.0042 (11)	0.0035 (11)	−0.0035 (11)
C18	0.0273 (14)	0.0193 (13)	0.0216 (14)	−0.0028 (10)	0.0072 (11)	0.0000 (10)
C19	0.0204 (12)	0.0172 (11)	0.0208 (13)	0.0029 (10)	0.0067 (10)	0.0014 (10)
C20	0.0211 (12)	0.0195 (12)	0.0206 (13)	0.0027 (10)	0.0035 (10)	0.0010 (10)
C21	0.0186 (12)	0.0202 (12)	0.0285 (14)	0.0023 (10)	0.0036 (10)	0.0015 (11)
C22	0.0220 (13)	0.0232 (13)	0.0288 (14)	0.0083 (10)	0.0121 (11)	0.0072 (11)
C23	0.0261 (14)	0.0247 (13)	0.0204 (13)	0.0055 (11)	0.0068 (11)	0.0004 (11)
C24	0.0200 (13)	0.0217 (13)	0.0219 (14)	0.0034 (9)	0.0035 (10)	−0.0014 (10)
F1	0.0512 (12)	0.0376 (10)	0.0654 (14)	0.0228 (9)	0.0007 (10)	−0.0194 (10)
F2	0.0414 (10)	0.0277 (9)	0.0329 (9)	−0.0123 (7)	−0.0064 (7)	−0.0050 (7)
F3	0.0384 (9)	0.0350 (9)	0.0193 (8)	0.0009 (7)	−0.0031 (7)	0.0061 (7)
F4	0.0269 (8)	0.0403 (9)	0.0345 (9)	0.0051 (7)	0.0176 (7)	0.0087 (7)

Geometric parameters (Å, º)

Sn1—C7	2.125 (3)	C11—H11	0.9500
Sn1—C13	2.130 (3)	C12—H12	0.9500
Sn1—C1	2.132 (2)	C13—C14	1.391 (4)
Sn1—C19	2.141 (3)	C13—C18	1.395 (4)
C1—C2	1.386 (4)	C14—C15	1.378 (4)
C1—C6	1.392 (4)	C14—H14	0.9500
C2—C3	1.382 (4)	C15—C16	1.379 (4)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.370 (5)	C16—F3	1.354 (3)
C3—H3	0.9500	C16—C17	1.366 (4)
C4—F1	1.349 (3)	C17—C18	1.385 (4)
C4—C5	1.368 (5)	C17—H17	0.9500
C5—C6	1.384 (4)	C18—H18	0.9500
C5—H5	0.9500	C19—C20	1.389 (4)
C6—H6	0.9500	C19—C24	1.390 (4)
C7—C8	1.389 (4)	C20—C21	1.385 (4)
C7—C12	1.389 (4)	C20—H20	0.9500
C8—C9	1.384 (4)	C21—C22	1.367 (4)
C8—H8	0.9500	C21—H21	0.9500
C9—C10	1.368 (4)	C22—F4	1.358 (3)
C9—H9	0.9500	C22—C23	1.372 (4)
C10—F2	1.356 (3)	C23—C24	1.386 (4)
C10—C11	1.373 (4)	C23—H23	0.9500
C11—C12	1.381 (4)	C24—H24	0.9500
C7—Sn1—C13	110.75 (10)	C11—C12—C7	121.2 (3)
C7—Sn1—C1	111.36 (9)	C11—C12—H12	119.4
C13—Sn1—C1	111.49 (9)	C7—C12—H12	119.4
C7—Sn1—C19	109.01 (10)	C14—C13—C18	118.1 (2)
C13—Sn1—C19	107.06 (10)	C14—C13—Sn1	121.29 (18)
C1—Sn1—C19	106.97 (9)	C18—C13—Sn1	120.33 (18)
C2—C1—C6	118.4 (2)	C15—C14—C13	121.4 (2)
C2—C1—Sn1	119.42 (18)	C15—C14—H14	119.3
C6—C1—Sn1	122.14 (19)	C13—C14—H14	119.3
C3—C2—C1	121.5 (3)	C14—C15—C16	118.2 (2)
C3—C2—H2	119.2	C14—C15—H15	120.9
C1—C2—H2	119.2	C16—C15—H15	120.9
C4—C3—C2	118.0 (3)	F3—C16—C17	118.9 (2)
C4—C3—H3	121.0	F3—C16—C15	118.4 (2)
C2—C3—H3	121.0	C17—C16—C15	122.8 (2)
F1—C4—C5	118.9 (3)	C16—C17—C18	118.2 (2)
F1—C4—C3	118.5 (3)	C16—C17—H17	120.9
C5—C4—C3	122.6 (3)	C18—C17—H17	120.9
C4—C5—C6	118.7 (3)	C17—C18—C13	121.3 (2)
C4—C5—H5	120.6	C17—C18—H18	119.3
C6—C5—H5	120.6	C13—C18—H18	119.3
C5—C6—C1	120.6 (3)	C20—C19—C24	118.4 (2)
C5—C6—H6	119.7	C20—C19—Sn1	120.89 (19)
C1—C6—H6	119.7	C24—C19—Sn1	120.74 (19)
C8—C7—C12	118.4 (2)	C21—C20—C19	121.4 (2)
C8—C7—Sn1	120.21 (18)	C21—C20—H20	119.3
C12—C7—Sn1	121.35 (19)	C19—C20—H20	119.3
C9—C8—C7	121.2 (2)	C22—C21—C20	117.8 (2)
C9—C8—H8	119.4	C22—C21—H21	121.1
C7—C8—H8	119.4	C20—C21—H21	121.1
C10—C9—C8	118.0 (2)	F4—C22—C21	118.5 (2)
C10—C9—H9	121.0	F4—C22—C23	118.1 (2)
C8—C9—H9	121.0	C21—C22—C23	123.3 (2)
F2—C10—C9	118.5 (2)	C22—C23—C24	117.9 (3)
F2—C10—C11	118.5 (2)	C22—C23—H23	121.1
C9—C10—C11	123.0 (2)	C24—C23—H23	121.1
C10—C11—C12	118.1 (3)	C23—C24—C19	121.2 (2)
C10—C11—H11	121.0	C23—C24—H24	119.4
C12—C11—H11	121.0	C19—C24—H24	119.4
C7—Sn1—C1—C2	−105.8 (2)	C7—Sn1—C13—C14	14.7 (2)
C13—Sn1—C1—C2	130.0 (2)	C1—Sn1—C13—C14	139.3 (2)
C19—Sn1—C1—C2	13.2 (2)	C19—Sn1—C13—C14	−104.0 (2)
C7—Sn1—C1—C6	73.8 (2)	C7—Sn1—C13—C18	−171.53 (19)
C13—Sn1—C1—C6	−50.4 (2)	C1—Sn1—C13—C18	−46.9 (2)
C19—Sn1—C1—C6	−167.2 (2)	C19—Sn1—C13—C18	69.7 (2)
C6—C1—C2—C3	−0.2 (4)	C18—C13—C14—C15	−0.8 (4)
Sn1—C1—C2—C3	179.4 (2)	Sn1—C13—C14—C15	173.1 (2)
C1—C2—C3—C4	−0.2 (4)	C13—C14—C15—C16	0.1 (4)
C2—C3—C4—F1	−179.9 (2)	C14—C15—C16—F3	179.7 (2)
C2—C3—C4—C5	0.8 (4)	C14—C15—C16—C17	0.5 (4)
F1—C4—C5—C6	179.6 (3)	F3—C16—C17—C18	−179.5 (2)
C3—C4—C5—C6	−1.1 (4)	C15—C16—C17—C18	−0.3 (4)
C4—C5—C6—C1	0.7 (4)	C16—C17—C18—C13	−0.4 (4)
C2—C1—C6—C5	−0.1 (4)	C14—C13—C18—C17	1.0 (4)
Sn1—C1—C6—C5	−179.7 (2)	Sn1—C13—C18—C17	−173.0 (2)
C13—Sn1—C7—C8	112.0 (2)	C7—Sn1—C19—C20	−160.55 (19)
C1—Sn1—C7—C8	−12.7 (2)	C13—Sn1—C19—C20	−40.7 (2)
C19—Sn1—C7—C8	−130.5 (2)	C1—Sn1—C19—C20	78.9 (2)
C13—Sn1—C7—C12	−67.6 (2)	C7—Sn1—C19—C24	20.9 (2)
C1—Sn1—C7—C12	167.8 (2)	C13—Sn1—C19—C24	140.7 (2)
C19—Sn1—C7—C12	50.0 (2)	C1—Sn1—C19—C24	−99.7 (2)
C12—C7—C8—C9	1.2 (4)	C24—C19—C20—C21	0.4 (4)
Sn1—C7—C8—C9	−178.30 (19)	Sn1—C19—C20—C21	−178.25 (19)
C7—C8—C9—C10	0.3 (4)	C19—C20—C21—C22	0.0 (4)
C8—C9—C10—F2	177.2 (2)	C20—C21—C22—F4	178.4 (2)
C8—C9—C10—C11	−1.9 (4)	C20—C21—C22—C23	−0.5 (4)
F2—C10—C11—C12	−177.2 (3)	F4—C22—C23—C24	−178.2 (2)
C9—C10—C11—C12	1.9 (4)	C21—C22—C23—C24	0.7 (4)
C10—C11—C12—C7	−0.3 (4)	C22—C23—C24—C19	−0.3 (4)
C8—C7—C12—C11	−1.2 (4)	C20—C19—C24—C23	−0.2 (4)
Sn1—C7—C12—C11	178.3 (2)	Sn1—C19—C24—C23	178.45 (19)