(2-Methyl-2-phenyl­propyl)­tri­phenyl­stannane

Howie, R.A.; Wardell, J.L.

doi:10.1107/S160053680402330X

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 60| Part 10| October 2004| Pages m1536-m1538

https://doi.org/10.1107/S160053680402330X

(2-Methyl-2-phenylpropyl)triphenylstannane

R. Alan Howie ^a ^* and James L. Wardell ^b

^aDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, and ^bDepartamento de Química Inorgânica, Instituto de Química, Universidade Federal do Rio de Janeiro, CP 68563, 21945-970 Rio de Janeiro, RJ, Brazil
^*Correspondence e-mail: r.a.howie@abdn.ac.uk

(Received 13 September 2004; accepted 20 September 2004; online 30 September 2004)

Bond lengths and angles in the title compound, [Sn(C₆H₅)₃(C₁₀H₁₃)], are as expected for a molecule of this kind. The packing of the molecules in well defined layers results in a number of C—H⋯π intermolecular contacts.

Comment

One component of the title compound, (I), is the 2-methyl-2-phenylpropyl or neophyl group (neo). The compound may therefore be formulated as (neo)Ph₃Sn. Fig. 1 is a drawing of the molecule, and distances and angles involving Sn are given in Table 1. These, along with benzene ring C—C distances and internal C—C—C angles, and distances and angles involving alkyl C atoms of the neophyl group [1.363 (6)–1.400 (5) Å and 117.2 (3)–121.2 (3)°, and 1.524 (4)–1.536 (5) Å and 106.3 (3)–112.0 (3)°, respectively], are unremarkable for a compound of this kind. However, two notable features are present in the structure. The first of these concerns the disposition within the molecule of the phenyl groups bonded directly to the Sn atom. For convenience in what follows, the four phenyl groups present in the molecule are designated as Ph1 with ring centroid Cg1, comprising atoms C5–C10, Ph2 with centroid Cg2, comprising C11–C16, Ph3 with centroid Cg3, comprising C17–C22, and Ph4 with centroid Cg4, comprising C23–C28. As is clearly shown in Fig. 1, Ph1 is part of the neophyl group and Ph2–Ph4 are the phenyl groups directly bonded to Sn. Ph2–Ph4 adopt the propeller-shaped configuration relative to Sn that is characteristic of the Ph₃Sn moiety, but the dihedral angles between their least-squares planes cover the unusually wide range of 49.55 (11)–87.13 (12)°. The values for the displacements of selected atoms from the plane defined by C11, C17 and C23 (see deposited CIF for details) confirm the propeller-shaped configuration but show that Ph2 has the greatest tilt relative to the reference plane and Ph3 the least. This configuration is attributed to the need to accommodate the steric requirements of the neophyl substituent.

The second notable feature of this structure is the manner in which the molecules are packed in layers (Fig. 2) parallel to (010), b/2 thick and centred on y = 0 and $[1\over2]$ . This arrangement, with phenyl groups directly attached to Sn on the surfaces of the layers, favours a number of C—H⋯π intermolecular contacts, as given in Table 2 and shown, in part, in Fig. 2. The contacts shown in Fig. 2 are those that occur within the layers of molecules. The contact present in Table 2 that is not shown in Fig. 2 is the interlayer contact C14—H14⋯Cg4^vii. The H⋯Cg distances are all greater than 2.98 Å and the significance of these interactions in terms of the formation of even very weak bonds, as distinct from simple packing requirements, remains doubtful, although they can be regarded as electrostatic interactions.

Figure 1
The molecule of (I

). Non-H atoms are shown as 50% probability displacement ellipsoids and H atoms as small spheres of arbitrary radii.

Figure 2
Molecules of (I

) in a layer parallel to (010) and centred on x = 1. Dashed lines indicate C—H⋯π contacts. Non-H atoms are shown as 50% probability displacement ellipsoids and H atoms as small spheres of arbitrary radii. Selected atoms are labelled. [Symmetry codes: (i) 1 −x, 2 − y, z; (ii) $[3\over 2]$ − x, y, z − $[1\over 2]$ ; (iii) x − $[1\over2]$ , 2 − y, z − $[1\over2]$ ; (iv) x, y, z − 1; (v) 1 − x, 2 − y, z − 1.]

Experimental

Compound (I) was obtained from the Grignard reaction of neophyl magnesium bromide, neoMgBr, prepared from neoBr (10.7 g, 0.05 mol) and Mg (0.18 g, 0.075 mol) in tetrahydrofuran (50 ml) with Ph₃SnCl (14.5 g, 0.038 mol). Crystals suitable for analysis (m.p. 367–368 K) were obtained by recrystallization from ethanol. ¹H NMR (400 MHz, CDCl₃): δ 1.48 (s, 6H, Me), 2.18 [s, 2H, J(^119,117Sn–¹H) = 56.1 Hz, CH₂Sn], 7.1–7.2 (m, 5H, Ph_neo), 7.3–7.5 (m, 15H, PhSn). ¹³C NMR (100 MHz, CDCl₃): δ 31.9 [J(^119,117Sn–¹³C) = 392, 376 Hz, CH₂], 33.1 [J(^119,117Sn–¹³C) = 64.8 Hz, CMe₂], 38.1 [J(^119,117Sn–¹³C) = 18.2 Hz, Me], 125.3 (C_m, Ph_neo), 125.7 (C_p, Ph_neo), 128.2 (C_o, Ph_neo), 128.3 [J(^119,117Sn–¹³C) = 48.6 Hz, C_m, PhSn], 128.5 [J(^119,117Sn–¹³C) = 10.6 Hz, C_p, PhSn], 136.9 [J(^119,117Sn–¹³C) = 35 Hz, C_o, PhSn], 139.8 [J(^119,117Sn–¹³C) = 483 and 461 Hz, C_ipso, PhSn], 150.1 (C_ipso, Ph_neo). ¹¹⁹Sn NMR (93 MHz, CDCl₃): δ −115.6.

Crystal data

[Sn(C₆H₅)₃(C₁₀H₁₃)]
M_r = 483.19
Orthorhombic, Aba2
a = 22.8724 (5) Å
b = 17.0573 (4) Å
c = 11.6326 (3) Å
V = 4538.36 (19) Å³
Z = 8
D_x = 1.414 Mg m⁻³
Mo Kα radiation
Cell parameters from 4339 reflections
θ = 2.9–27.5°
μ = 1.14 mm⁻¹
T = 120 (2) K
Block, colourless
0.60 × 0.35 × 0.30 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995 , 1997 ) T_min = 0.556, T_max = 0.711
7972 measured reflections
3545 independent reflections
3358 reflections with I > 2σ(I)
R_int = 0.048
θ_max = 27.5°
h = −26 → 29
k = −18 → 22
l = −10 → 14

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.067
S = 1.08
3545 reflections
265 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0313P)² + 2.271P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.005
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.79 e Å⁻³
Extinction correction: SHELXL97
Extinction coefficient: 0.00349 (14)
Absolute structure: Flack (1983 ), 887 Friedel pairs
Flack parameter = 0.04 (3)

Table 1
Selected geometric parameters (Å, °)

Sn1—C11	2.139 (4)
Sn1—C23	2.142 (3)
Sn1—C17	2.145 (4)
Sn1—C1	2.163 (3)

C11—Sn1—C23	109.53 (15)
C11—Sn1—C17	106.97 (11)
C23—Sn1—C17	107.73 (15)
C11—Sn1—C1	103.98 (15)
C23—Sn1—C1	118.93 (11)
C17—Sn1—C1	109.10 (13)
C2—C1—Sn1	121.1 (2)

Table 2
Distances and angles (Å, °) associated with intermolecular C—H⋯π contacts in (I)

C—H⋯Cg^a	H⋯Cg	H_perp^b	γ^c	C—H⋯Cg	C⋯Cg
C6—H6⋯Cg2ⁱⁱ	3.10	3.03	12	143	3.90
C12—H12⋯Cg4^vi	3.21	3.02	20	127	3.86
C14—H14⋯Cg4^vii	3.19	3.08	15	144	4.00
C16—H16⋯Cg3^viii	3.18	3.05	16	140	3.95
C18—H18⋯Cg1ⁱⁱ	3.24	3.13	14	133	3.94
C25—H25⋯Cg3^vi	2.98	2.95	8	137	3.74
Notes: (a) Cg1–Cg4 are, respectively, the centroids of the rings defined byC5–C10, C11–C16, C17–C22 and C23–C28; (b) H_perp is the perpendicular distance of H from the π-acceptor ring; (c) γ is the angle at H between H⋯Cg and H_perp. Symmetry codes: (ii) $[{{3}\over{2}} -x, y, z-{{1}\over{2}}]$ ; (vi) 2-x, 2-y, z; (vii) $[x, y-{{1}\over{2}}, {{1} \over {2}} + z]$ ; (viii) $[{{3} \over {2}}-x, y, {{1} \over {2}} + z]$ .

In the final stages of refinement, H atoms were placed in calculated positions with C—H = 0.99, 0.98 and 0.95 Å for methylene, methyl and aryl H, respectively, and refined with a riding model, with U_iso(H) = 1.5U_eq(C) for methyl H and 1.2U_eq(C) otherwise.

Data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Hooft, 1998 ); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S160053680402330X/cf6377sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680402330X/cf6377Isup2.hkl

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

(2-Methyl-2-phenylpropyl)triphenylstannane top

Crystal data top

[Sn(C₆H₅)₃(C₁₀H₁₃)]	D_x = 1.414 Mg m⁻³
M_r = 483.19	Melting point = 367–368 K
Orthorhombic, Aba2	Mo Kα radiation, λ = 0.71073 Å
a = 22.8724 (5) Å	Cell parameters from 4339 reflections
b = 17.0573 (4) Å	θ = 2.9–27.5°
c = 11.6326 (3) Å	µ = 1.14 mm⁻¹
V = 4538.36 (19) Å³	T = 120 K
Z = 8	Block, colourless
F(000) = 1968	0.60 × 0.35 × 0.30 mm

Data collection top

Nonius KappaCCD area-detector diffractometer	3545 independent reflections
Radiation source: Nonius FR591 rotating anode	3358 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
φ and ω scans	h = −26→29
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −18→22
T_min = 0.556, T_max = 0.711	l = −10→14
7972 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.027	w = 1/[σ²(F_o²) + (0.0313P)² + 2.271P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.067	(Δ/σ)_max = 0.005
S = 1.08	Δρ_max = 0.75 e Å⁻³
3545 reflections	Δρ_min = −0.79 e Å⁻³
265 parameters	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.00349 (14)
Primary atom site location: heavy-atom method	Absolute structure: Flack (1983), 887 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.04 (3)

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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 2.6828(0.0367) x + 13.0476(0.0202) y + 7.3675(0.0164) z = 18.1598(0.0359)

* -0.0057 (0.0029) C11 * 0.0031 (0.0027) C12 * 0.0041 (0.0027) C13 * -0.0088 (0.0030) C14 * 0.0061 (0.0028) C15 * 0.0012 (0.0028) C16 - 0.1163 (0.0065) Sn1 0.7869 (0.0083) C1 1.3970 (0.0107) C2 2.6003 (0.0112) C3 0.3629 (0.0125) C4 1.7851 (0.0118) C5 0.8100 (0.0129) C6 3.0837 (0.0117) C10

Rms deviation of fitted atoms = 0.0054

22.8025(0.0024) x + 0.4535(0.0221) y + 0.8545(0.0157) z = 20.5373(0.0207)

Angle to previous plane (with approximate e.s.d.) = 87.13 (0.12)

* 0.0007 (0.0022) C17 * 0.0013 (0.0022) C18 * -0.0004 (0.0024) C19 * -0.0024 (0.0025) C20 * 0.0043 (0.0023) C21 * -0.0035 (0.0021) C22 0.0422 (0.0046) Sn1 - 1.9600 (0.0062) C1 - 2.4819 (0.0070) C2 - 1.6823 (0.0084) C3 - 2.3051 (0.0066) C4 - 3.9562 (0.0072) C5 - 4.9060 (0.0062) C6 - 4.4044 (0.0089) C10

Rms deviation of fitted atoms = 0.0025

14.5251(0.0256) x - 10.8057(0.0183) y + 5.1420(0.0153) z = 6.6719(0.0425)

Angle to previous plane (with approximate e.s.d.) = 49.55 (0.11)

* -0.0091 (0.0022) C23 * 0.0061 (0.0024) C24 * -0.0007 (0.0025) C25 * -0.0017 (0.0025) C26 * -0.0014 (0.0025) C27 * 0.0067 (0.0024) C28 0.0144 (0.0051) Sn1 - 1.5915 (0.0075) C1 - 3.0254 (0.0068) C2 - 3.0824 (0.0060) C3 - 3.4702 (0.0064) C4 - 3.8980 (0.0085) C5 - 4.2631 (0.0096) C6 - 4.2916 (0.0092) C10

Rms deviation of fitted atoms = 0.0053

- 2.6828(0.0367) x + 13.0476(0.0202) y + 7.3675(0.0164) z = 18.1598(0.0359)

Angle to previous plane (with approximate e.s.d.) = 73.79 (0.11)

* -0.0057 (0.0029) C11 * 0.0031 (0.0027) C12 * 0.0041 (0.0027) C13 * -0.0088 (0.0030) C14 * 0.0061 (0.0028) C15 * 0.0012 (0.0028) C16

Rms deviation of fitted atoms = 0.0054

20.5468(0.0114) x - 7.4322(0.0177) y - 0.6542(0.0220) z = 10.0988(0.0337)

Angle to previous plane (with approximate e.s.d.) = 61.69 (0.13)

* 0.0000 (0.0000) C11 * 0.0000 (0.0000) C17 * 0.0000 (0.0000) C23 - 0.7616 (0.0017) Sn1 1.2164 (0.0060) C12 - 0.6920 (0.0067) C16 - 0.0626 (0.0064) C18 0.6062 (0.0048) C22 0.7904 (0.0047) C24 - 0.2462 (0.0051) C28

Rms deviation of fitted atoms = 0.0000

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	0.845344 (7)	0.992790 (9)	0.99869 (6)	0.01462 (8)
C1	0.75596 (12)	1.03149 (18)	1.0202 (3)	0.0181 (8)
H1A	0.7305	0.9881	0.9941	0.022*
H1B	0.7492	1.0377	1.1038	0.022*
C2	0.73376 (14)	1.10661 (18)	0.9619 (3)	0.0183 (7)
C3	0.76558 (12)	1.17785 (16)	1.0106 (4)	0.0236 (7)
H3A	0.7483	1.2258	0.9790	0.035*
H3B	0.8070	1.1753	0.9897	0.035*
H3C	0.7618	1.1782	1.0946	0.035*
C4	0.74644 (16)	1.1031 (2)	0.8323 (3)	0.0272 (8)
H4A	0.7299	1.0549	0.8002	0.041*
H4B	0.7888	1.1037	0.8197	0.041*
H4C	0.7287	1.1486	0.7944	0.041*
C5	0.66819 (13)	1.11003 (17)	0.9846 (4)	0.0185 (8)
C6	0.62981 (15)	1.0626 (2)	0.9223 (4)	0.0283 (8)
H6	0.6446	1.0308	0.8619	0.034*
C7	0.57044 (15)	1.0612 (2)	0.9473 (4)	0.0377 (10)
H7	0.5451	1.0286	0.9036	0.045*
C8	0.54811 (15)	1.1062 (2)	1.0342 (4)	0.0379 (12)
H8	0.5076	1.1046	1.0516	0.046*
C9	0.58504 (16)	1.1536 (2)	1.0957 (4)	0.0295 (9)
H9	0.5698	1.1853	1.1557	0.035*
C10	0.64437 (15)	1.1557 (2)	1.0713 (3)	0.0217 (8)
H10	0.6692	1.1891	1.1149	0.026*
C11	0.86120 (18)	0.9211 (3)	1.1464 (4)	0.0191 (9)
C12	0.91749 (16)	0.9093 (2)	1.1890 (3)	0.0258 (8)
H12	0.9496	0.9357	1.1547	0.031*
C13	0.92684 (17)	0.8593 (2)	1.2811 (3)	0.0329 (9)
H13	0.9653	0.8518	1.3098	0.039*
C14	0.8805 (2)	0.8205 (3)	1.3313 (4)	0.0360 (11)
H14	0.8873	0.7854	1.3933	0.043*
C15	0.82512 (19)	0.8324 (3)	1.2919 (4)	0.0380 (10)
H15	0.7932	0.8066	1.3280	0.046*
C16	0.81499 (15)	0.8818 (2)	1.2002 (3)	0.0271 (8)
H16	0.7762	0.8891	1.1732	0.032*
C17	0.85054 (13)	0.9177 (3)	0.8511 (4)	0.0152 (9)
C18	0.85421 (13)	0.9461 (2)	0.7388 (3)	0.0195 (7)
H18	0.8537	1.0011	0.7258	0.023*
C19	0.85860 (15)	0.8958 (2)	0.6464 (3)	0.0218 (8)
H19	0.8610	0.9161	0.5705	0.026*
C20	0.85941 (16)	0.8161 (3)	0.6648 (4)	0.0254 (9)
H20	0.8622	0.7814	0.6011	0.030*
C21	0.85618 (15)	0.7860 (2)	0.7749 (3)	0.0244 (8)
H21	0.8572	0.7310	0.7871	0.029*
C22	0.85135 (12)	0.8369 (2)	0.8677 (3)	0.0192 (7)
H22	0.8486	0.8163	0.9433	0.023*
C23	0.91309 (12)	1.07891 (15)	0.9837 (3)	0.0160 (7)
C24	0.94898 (13)	1.08020 (19)	0.8880 (3)	0.0223 (7)
H24	0.9432	1.0428	0.8287	0.027*
C25	0.99346 (13)	1.1356 (2)	0.8774 (4)	0.0263 (9)
H25	1.0174	1.1363	0.8106	0.032*
C26	1.00264 (13)	1.1892 (2)	0.9640 (4)	0.0267 (11)
H26	1.0330	1.2269	0.9572	0.032*
C27	0.96772 (16)	1.1881 (2)	1.0605 (3)	0.0268 (8)
H27	0.9740	1.2254	1.1200	0.032*
C28	0.92344 (15)	1.13297 (19)	1.0712 (3)	0.0234 (8)
H28	0.9000	1.1321	1.1386	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Sn1	0.01299 (11)	0.01505 (11)	0.01581 (13)	0.00074 (6)	0.00005 (16)	−0.0003 (2)
C1	0.0115 (12)	0.0237 (14)	0.019 (2)	0.0051 (11)	0.0021 (13)	0.0003 (15)
C2	0.0195 (15)	0.0180 (14)	0.0174 (18)	0.0008 (12)	0.0000 (13)	0.0017 (12)
C3	0.0196 (14)	0.0187 (12)	0.033 (2)	−0.0002 (10)	0.0042 (19)	0.001 (2)
C4	0.0250 (17)	0.041 (2)	0.0159 (19)	0.0098 (16)	0.0050 (15)	0.0088 (17)
C5	0.0160 (13)	0.0162 (12)	0.023 (2)	0.0019 (10)	0.0006 (16)	0.0035 (17)
C6	0.0227 (16)	0.0250 (17)	0.037 (2)	0.0012 (15)	−0.0026 (18)	−0.0072 (17)
C7	0.0192 (16)	0.0314 (19)	0.063 (3)	−0.0014 (16)	−0.0090 (18)	−0.006 (2)
C8	0.0164 (16)	0.0363 (19)	0.061 (3)	0.0037 (14)	0.0084 (18)	0.011 (2)
C9	0.0265 (18)	0.0283 (18)	0.034 (2)	0.0122 (15)	0.0087 (17)	0.0077 (17)
C10	0.0241 (16)	0.0235 (17)	0.017 (2)	0.0067 (14)	0.0008 (15)	0.0035 (15)
C11	0.0216 (17)	0.017 (2)	0.019 (2)	0.0023 (18)	−0.0031 (17)	−0.0006 (18)
C12	0.0206 (16)	0.0315 (18)	0.025 (2)	0.0049 (14)	0.0000 (15)	−0.0019 (16)
C13	0.031 (2)	0.039 (2)	0.029 (2)	0.0125 (17)	−0.0136 (18)	−0.0015 (18)
C14	0.050 (3)	0.039 (3)	0.019 (2)	0.018 (2)	0.005 (2)	0.0079 (19)
C15	0.036 (2)	0.041 (2)	0.037 (3)	0.0092 (19)	0.012 (2)	0.017 (2)
C16	0.0196 (16)	0.0318 (18)	0.030 (2)	0.0045 (15)	0.0013 (17)	0.0047 (17)
C17	0.0129 (14)	0.018 (2)	0.015 (2)	0.0020 (13)	−0.0005 (13)	−0.0036 (18)
C18	0.0177 (15)	0.0161 (15)	0.0246 (19)	0.0002 (13)	−0.0018 (14)	0.0019 (15)
C19	0.0222 (17)	0.0281 (18)	0.0150 (18)	0.0007 (14)	−0.0001 (15)	−0.0004 (16)
C20	0.0226 (18)	0.022 (2)	0.031 (3)	−0.0005 (17)	−0.0023 (17)	−0.0120 (18)
C21	0.0266 (17)	0.0149 (16)	0.032 (2)	−0.0033 (14)	0.0009 (16)	−0.0065 (16)
C22	0.0174 (14)	0.0182 (16)	0.022 (2)	−0.0042 (12)	0.0037 (14)	−0.0001 (15)
C23	0.0134 (12)	0.0136 (11)	0.021 (2)	−0.0005 (9)	−0.0024 (14)	−0.0004 (15)
C24	0.0184 (15)	0.0217 (16)	0.027 (2)	−0.0042 (13)	0.0014 (15)	−0.0041 (15)
C25	0.0179 (16)	0.032 (2)	0.029 (2)	−0.0046 (13)	0.0009 (16)	0.0026 (19)
C26	0.0173 (17)	0.0207 (16)	0.042 (3)	−0.0012 (12)	−0.0056 (14)	−0.0027 (16)
C27	0.0223 (18)	0.0259 (18)	0.032 (2)	0.0004 (15)	−0.0065 (18)	−0.0122 (17)
C28	0.0196 (16)	0.0227 (16)	0.028 (2)	0.0022 (13)	−0.0021 (15)	−0.0063 (16)

Geometric parameters (Å, º) top

Sn1—C11	2.139 (4)	C12—H12	0.950
Sn1—C23	2.142 (3)	C13—C14	1.379 (6)
Sn1—C17	2.145 (4)	C13—H13	0.950
Sn1—C1	2.163 (3)	C14—C15	1.363 (6)
C1—C2	1.536 (4)	C14—H14	0.950
C1—H1A	0.990	C15—C16	1.378 (5)
C1—H1B	0.990	C15—H15	0.950
C2—C5	1.524 (4)	C16—H16	0.950
C2—C3	1.526 (4)	C17—C22	1.392 (6)
C2—C4	1.536 (5)	C17—C18	1.397 (6)
C3—H3A	0.980	C18—C19	1.379 (5)
C3—H3B	0.980	C18—H18	0.950
C3—H3C	0.980	C19—C20	1.377 (6)
C4—H4A	0.980	C19—H19	0.950
C4—H4B	0.980	C20—C21	1.382 (6)
C4—H4C	0.980	C20—H20	0.950
C5—C10	1.386 (5)	C21—C22	1.389 (5)
C5—C6	1.397 (5)	C21—H21	0.950
C6—C7	1.389 (5)	C22—H22	0.950
C6—H6	0.950	C23—C24	1.383 (5)
C7—C8	1.368 (5)	C23—C28	1.393 (5)
C7—H7	0.950	C24—C25	1.394 (4)
C8—C9	1.371 (5)	C24—H24	0.950
C8—H8	0.950	C25—C26	1.377 (6)
C9—C10	1.387 (5)	C25—H25	0.950
C9—H9	0.950	C26—C27	1.378 (6)
C10—H10	0.950	C26—H26	0.950
C11—C12	1.394 (5)	C27—C28	1.388 (5)
C11—C16	1.400 (5)	C27—H27	0.950
C12—C13	1.386 (5)	C28—H28	0.950

C11—Sn1—C23	109.53 (15)	C13—C12—C11	120.4 (4)
C11—Sn1—C17	106.97 (11)	C13—C12—H12	119.8
C23—Sn1—C17	107.73 (15)	C11—C12—H12	119.8
C11—Sn1—C1	103.98 (15)	C14—C13—C12	120.3 (4)
C23—Sn1—C1	118.93 (11)	C14—C13—H13	119.8
C17—Sn1—C1	109.10 (13)	C12—C13—H13	119.8
C2—C1—Sn1	121.1 (2)	C15—C14—C13	120.0 (4)
C2—C1—H1A	107.1	C15—C14—H14	120.0
Sn1—C1—H1A	107.1	C13—C14—H14	120.0
C2—C1—H1B	107.1	C14—C15—C16	120.5 (4)
Sn1—C1—H1B	107.1	C14—C15—H15	119.7
H1A—C1—H1B	106.8	C16—C15—H15	119.7
C5—C2—C3	112.0 (3)	C15—C16—C11	120.8 (4)
C5—C2—C1	106.3 (3)	C15—C16—H16	119.6
C3—C2—C1	110.0 (3)	C11—C16—H16	119.6
C5—C2—C4	110.9 (3)	C22—C17—C18	118.2 (4)
C3—C2—C4	107.8 (3)	C22—C17—Sn1	118.8 (3)
C1—C2—C4	109.8 (3)	C18—C17—Sn1	123.0 (3)
C2—C3—H3A	109.5	C19—C18—C17	121.2 (3)
C2—C3—H3B	109.5	C19—C18—H18	119.4
H3A—C3—H3B	109.5	C17—C18—H18	119.4
C2—C3—H3C	109.5	C20—C19—C18	119.6 (4)
H3A—C3—H3C	109.5	C20—C19—H19	120.2
H3B—C3—H3C	109.5	C18—C19—H19	120.2
C2—C4—H4A	109.5	C19—C20—C21	120.7 (4)
C2—C4—H4B	109.5	C19—C20—H20	119.7
H4A—C4—H4B	109.5	C21—C20—H20	119.7
C2—C4—H4C	109.5	C20—C21—C22	119.5 (3)
H4A—C4—H4C	109.5	C20—C21—H21	120.2
H4B—C4—H4C	109.5	C22—C21—H21	120.2
C10—C5—C6	117.2 (3)	C21—C22—C17	120.8 (4)
C10—C5—C2	122.3 (3)	C21—C22—H22	119.6
C6—C5—C2	120.4 (3)	C17—C22—H22	119.6
C7—C6—C5	121.1 (4)	C24—C23—C28	118.4 (3)
C7—C6—H6	119.5	C24—C23—Sn1	120.4 (2)
C5—C6—H6	119.5	C28—C23—Sn1	121.2 (2)
C8—C7—C6	120.6 (4)	C23—C24—C25	121.1 (3)
C8—C7—H7	119.7	C23—C24—H24	119.5
C6—C7—H7	119.7	C25—C24—H24	119.5
C7—C8—C9	119.1 (3)	C26—C25—C24	119.8 (4)
C7—C8—H8	120.4	C26—C25—H25	120.1
C9—C8—H8	120.4	C24—C25—H25	120.1
C8—C9—C10	120.8 (4)	C25—C26—C27	119.9 (3)
C8—C9—H9	119.6	C25—C26—H26	120.0
C10—C9—H9	119.6	C27—C26—H26	120.0
C5—C10—C9	121.2 (3)	C26—C27—C28	120.3 (3)
C5—C10—H10	119.4	C26—C27—H27	119.8
C9—C10—H10	119.4	C28—C27—H27	119.8
C12—C11—C16	117.9 (4)	C27—C28—C23	120.5 (3)
C12—C11—Sn1	121.6 (3)	C27—C28—H28	119.8
C16—C11—Sn1	120.4 (3)	C23—C28—H28	119.8

C12—C11—Sn1—C1	−155.0 (3)	Sn1—C1—C2—C3	−64.9 (4)
C16—C11—Sn1—C1	27.8 (4)	Sn1—C1—C2—C4	53.6 (3)
C18—C17—Sn1—C1	81.4 (3)	Sn1—C1—C2—C5	173.7 (2)
C22—C17—Sn1—C1	−99.8 (3)	C1—C2—C5—C6	−76.8 (4)
C24—C23—Sn1—C1	−122.4 (3)	C1—C2—C5—C10	99.0 (4)
C28—C23—Sn1—C1	59.8 (3)	C3—C2—C5—C6	163.0 (3)
C11—Sn1—C1—C2	156.5 (3)	C3—C2—C5—C10	−21.2 (5)
C17—Sn1—C1—C2	−89.6 (3)	C4—C2—C5—C6	42.5 (5)
C23—Sn1—C1—C2	34.4 (3)	C4—C2—C5—C10	−141.6 (3)

Distances and angles (Å, °) associated with intermolecular C—H..π contacts in (I) top

C—H···Cg^a	H···Cg	H_perp^b	γ^c	C—H···Cg	C···Cg
C6—H6···Cg2ⁱⁱ	3.10	3.03	12	143	3.90
C12—H12···Cg4ⁱ	3.21	3.02	20	127	3.86
C14—H14···Cg4ⁱⁱⁱ	3.19	3.08	15	144	4.00
C16—H16···Cg3^iv	3.18	3.05	16	140	3.95
C18—H18···Cg1ⁱⁱ	3.24	3.13	14	133	3.94
C25—H25···Cg3ⁱ	2.98	2.95	8	137	3.74

Notes: (a) Cg1–Cg4 are, respectively, the centroids of the rings defined by C5–C10, C11–C16, C17–C22 and C23–C28; (b) H_perp is the perpendicular distance of H from the π-acceptor ring; (c) γ is the angle at H between H···Cg and H_perp. Symmetry codes: (i) 2-x, 2-y, z; (ii) 3/2-x, y, z-1/2; (iii) x, y-1/2, 1/2+z; (iv) 3/2-x, y, 1/2+z.

Acknowledgements

The authors thank CNPq, Brazil, for financial support.

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