Isomorphous dichloro- and dibromo(2-methyl-2-phenyl­propyl)­phenylstannane, both displaying the same intramolecular π–π interaction at 120 K

The title compounds, di­chloro- and di­bromo­neophyl­phenyl­tin, [SnCl₂(C₆H₅)(C₁₀H₁₃)] and [SnBr₂(C₆H₅)(C₁₀H₁₃)], respectively, are remarkable for the `U' shape of the mol­ecules, whereby the two phenyl groups are brought face-to-face in an arrangement that permits intermolecular C—H...π bonds to connect the mol­ecules into layers parallel to (100). Intermolecular Sn–halide bonds are notably absent from the structures.

S1. Comment

Numerous entries in the Cambridge Structural Database (CSD; Allen, 2002) reveal that simple non-functionalized diorganodihalotins, RR'SnX₂, exist in the solid state as molecular compounds sometimes exhibiting various types of intermolecular interaction. Regardless of the involvement of the tin centre in these intermolecular interactions, such as that noted for a series of compounds (with X = Cl) by Amini et al. (1987), they are generally weak. The interactions and conformations of the title compounds, (I) and (II), have been investigated. Fig. 1 shows the molecule of (I); this figure, with Br substituted for Cl, is equally appropriate for the molecule of (II). Selected bond lengths and angles for (I) and (II) are given in Table 1. The C—C distances and internal angles in the benzene rings of (I) and (II) (not given in Table 1) are in the ranges 1.346 (12)–1.406 (8) Å and 117.3 (10)122.6 (11)°, respectively, and are not discussed further. The Sn—C bond lengths and the angles at the Sn atom are similar for the two molecules. More significant, however, is the similarity of the intramolecular Sn—X [X = Cl for (I) and Br for (II)] bond lengths; as discussed in greater detail later, such a similiarity is not observed in other formally similar compounds. The torsion angles in Table 1 clearly demonstrate that, while (I) and (II) are isostructural, the sample crystals are, by chance, enantiomeric, i.e. of opposite polarity.

Totally unexpected, however, is the overall `U' shape of the molecules of (I) and (II), which brings the two benzene rings in the molecule face to face. The intramolecular interaction between the rings [designated as ring 1, with centroid Cg1, forming part of the 2-methyl-2-phenylpropyl (also known as neophyl) ligand, and ring 2, with centroid Cg2, bonded directly to the Sn atom] is characterized as follows [values for (II) are given in parentheses]. The distance between the ring centroids, Cg1—Cg2, vector A, is 3.940 (3.898) Å. The perpendicular distances from Cg1 to the plane of ring 2 (vector B), and from Cg2 to the plane of ring 1 (vector C), are 3.368 (3.416) and 3.757 (3.713) Å, respectively. The dihedral angle between the planes, the angle between vectors A and B at Cg1, and the angle between vectors A and C at Cg2 are, respectively, 14.0 (2) [11.1 (2)], 17.5 (17.7) and 31.3 (28.8)°. The intramolecular separation between these planes, the only face-to-face separation between them of any significance, is roughly comparable to that normally associated with π..π stacking (ca 3.4 Å; Pauling, 1960). For both (I) and (II), this conformation has the effect of bringing about the C—H..π interactions given in Table 2. These connect the molecules to form layers parallel to (100) (Fig. 2) and related to one another by cell translation. Of some interest in Fig. 2 and Table 2 is the fact that each C—H..π interaction is confined to a single ring type, which provides both the donated H atom and the benzene-ring acceptor. Ring 1 is employed in connecting molecules related to one another by the operation of a crystallographic twofold screw axis with equation 1/2,y,1/2, in which the ?donor-to-acceptor polarity in (I) is in the +b direction?. For ring 2, the equation of the twofold screw axis is 1/2,y,0, and the polarity of the interaction in (I) is now in the −b direction. Thus, in each case, the C—H..π interaction can be considered to connect chains of molecules propagated in the b direction, but the participation of the molecules in both chains connects them and completes the connectivity of the layer. Clearly, it is the orientation of the molecules and the resulting polarity of the C—H..π interactions that determine the polarity of the structure as a whole, which is compatible with the non-centrosymmetric space group P2₁. The layer surfaces are populated primarily by methyl groups, the edges of the phenyl groups and Cl atoms. There is, however, no evidence of C—H.·Cl or any other form of intermolecular interaction other than van der Waals interactions across the interlayer boundary. Indeed, the shortest intermolecular Sn..halide distances in (I) and (II) are of the order of 5.4 and 5.6 Å, respectively. The situation in (I) is in striking contrast to that found in the formally analogous compounds dichloro(diphenyl)tin, Ph₂SnCl₂ (III) (CSD, version 5.24, refcode DCDPSN; Greene & Bryan, 1971), and methylphenyltin(IV) dichloride, (IV) (CSD refcode GIJYAZ; Amini et al., 1987). Bokii et al. (1972) in re-evaluating the published results of Greene & Bryan (1971) showed that intermolecular Sn···Cl contacts [lengths now computed as being in the range 3.7697 (18)–3.8724 (19) Å] are present, inducing significant distortion of the Sn coordination and, in particular, accounting for the comparatively wide range [2.336 (2)–2.357 (2) Å] in the primary Sn—Cl bond lengths in (III). Likewise, for (IV), Amini et al. (1987) report primary Sn—Cl bonds in the range 2.36 (1)–2.39 (1) Å associated with intermolecular Sn···Cl contacts now computed to be in the range 3.422 (9)–3.806 (11) Å. Similar weak intermolecular Sn.·I bonds have been invoked by Howie & Wardell (1996) in explanation of features of the coordination of the Sn atom in diphenyltin diiodide (CSD refcode HIHCUW). Also present in (III), with no equivalent in the structures of (I) and (II), are aryl C—H···Cl hydrogen bonds; ?for C—H distances of 1.08 Å, the H···Cl and C···Cl distances fall in the ranges 2.80–2.81 and 3.449 (6)–3.825 (7) Å, respectively, and the C—H.·Cl angles range from 118 to 156°. Pairwise π···π and C—H..π contacts are present in all three structures, but in (III), the former are in the form of intermolecular contacts between centrosymmetrically related pairs of only one of the two molecules present in the asymmetric unit, as distinct from the intramolecular contact of this type present in (I) and (II). The presence of intermolecular Sn···Cl bonds in (III) and (IV) is clearly consistant with the differences in the lengths of the primary Sn—Cl bonds in these structures and their absence with the equivalence of the bonds in (I)?. The fact that the Sn—Cl bonds are longer in (I) than in (III) or (IV) is, however, surprising.

S2. Experimental

Compound (I) was obtained by reaction of [PhC(Me)₂CH₂]Ph₃Sn, (V), with HgCl₂ in acetone. Recrystallization from ethanol provided crystals suitable for analysis (m.p. 328–330 K). IR (nujol mull, cm⁻¹) ν: 344 s br, Sn—Cl. ¹H NMR (200 MHz, Me₂CO-d₆): δ: 1.53 [s, 6H, J(^119,117Sn-¹H) = 10.7 Hz, Me], 2.67 [s, 2H, J(^119,117Sn-¹H) = 78.4, 75.3 Hz, CH₂Sn], 7.3–7.7 [m, 10H, Ph]. ¹³C NMR (50 MHz, Me₂CO-d₆): δ: 32.7 [J(^119,117Sn-¹³C) = 67.2, 64.2 Hz, Me], 39.1 [J(^119,117Sn-¹³C) = 22 Hz, CMe₂], 49.1 [J(^119,117Sn-¹³C) = 548, 524 Hz, CH₂], 126.1 [C_m, Ph_neo], 127.5 [C_p, Ph_neo], 129.7 [J(^119,117Sn-¹³C) = 22 Hz, C_o, Ph_neo], 129.8 [J(^119,117Sn-¹³C) = 82.2, 78.4 Hz, C_m, PhSn], 131.6 [J(^119,117Sn-¹³C) = 16.7 Hz, C_p, PhSn], 135.4 [J(^119,117Sn-¹³C) = 65.0, 62.3 Hz, C_o, PhSn], 142.9 [J(^119,117Sn-¹³C) nd, C_ipso, PhSn], 150.5 [J(^119,117Sn-¹³C) = 55.5, 52.5 Hz, C_ipso, Ph_neo]. ¹¹⁹Sn NMR (75 MHz, Me₂CO-d₆): δ: −32.3 Compound (II) was obtained by reaction of (V) with Br₂ in acetone solution [the molar ratio of (V)/Br₂ was 1:2] and recrystallized from heptane (m.p. 318–320 K). IR (polythene film, cm⁻¹) ν: 252 br, Sn—Br. ¹H NMR (200 MHz, CDCl₃): δ: 1.58 [s, 6H, J(^119,117Sn-¹H) = 10.4 Hz, Me], 2.84 [s, 2H, J(^119,117Sn-¹H) = 73.6, 70.8 Hz, CH₂Sn], 7.3–7.7 [m, 10H, Ph]. ¹³C NMR (50 MHz, CDCl₃): δ: 32.4 [J(^119,117Sn-¹³C) = 69.4, 66.5 Hz, Me], 38.8 [J(^119,117Sn-¹³C) = 19.9 Hz, CMe₂], 49.4 [J(^119,117Sn-¹³C) = 475.7, 455.2 Hz, CH₂], 125.1 [C_m, Ph_neo], 127.0 [C_p, Ph_neo], 129.0 [J(^119,117Sn-¹³C) = 22.2 Hz, C_o, Ph_neo], 129.1 [J(^119,117Sn-¹³C) = 78.7, 75.6 Hz, C_m, PhSn], 130.8 [J(^119,117Sn-¹³C) = 16.4 Hz, C_p, PhSn], 134.2 [J(^119,117Sn-¹³C) = 65.0, 62.3 Hz, C_o, PhSn], 139.4 [J(^119,117Sn-¹³C) 637, 604 Hz, C_ipso, PhSn], 148.5 [J(^119,117Sn-¹³C) = 38 Hz, C_ipso, Ph_neo].

S3. Refinement

In the final stages of the refinement of (I), H atoms were introduced in calculated positions and treated with a riding model, with C—H distances of 0.95, 0.99 and 0.98 Å and U_iso(H) values of 1.2, 1.2 and 1.5 times U_eq of the parent C atom for, respectively, phenyl, methylene and methyl H atoms. The rotational orientation of the rigid-body methyl groups was also refined. Subsequent to the initial independent solution and refinement of the structure of (II), the structure was re-refined in an identical manner with the coordinates found for (I) as starting parameters, but with Br substituted for Cl. The number of Friedel pairs used to refine the absolute structure were 1373 and 1725 for (I) and (II), respectively.

Computing details

Data collection: DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) for (I); DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998) for (II). For both compounds, 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).

Figures

	Fig. 1. The molecule of (I), showing the atom-labelling scheme. This figure, with Br substituted for Cl, applies equally well to (II). Non-H atoms are shown as 50% probability displacement ellipsoids and H atoms are shown as spheres of arbitrary radii.
	Fig. 2. C—H···π interactions (dashed lines) between molecules of (I) in a layer parallel to (100). Non-H atoms are shown as 50% probability displacement ellipsoids and those H atoms involved in the contacts are shown as spheres of arbitrary radii. Selected atoms are labelled.

(I) Dichloro(2-methyl-2-phenylpropyl)phenylstannane

Crystal data

[SnCl2(C6H5)(C10H13)]	F(000) = 396
Mr = 399.89	Dx = 1.618 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4852 reflections
a = 9.1673 (3) Å	θ = 2.9–27.5°
b = 9.0698 (2) Å	µ = 1.87 mm^−1
c = 9.8939 (3) Å	T = 120 K
β = 93.8823 (17)°	Block, colourless
V = 820.75 (4) Å^3	0.24 × 0.22 × 0.14 mm
Z = 2

Data collection

Enraf–Nonius KappaCCD area-detector diffractometer	3375 independent reflections
Radiation source: Enraf–Nonius FR591 rotating anode	3239 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 2.9°
ϕ and ω scans to fill the Ewald sphere	h = −11→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −10→11
Tmin = 0.668, Tmax = 0.692	l = −11→12
6614 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)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.063	w = 1/[σ^2(Fo^2) + (0.0183P)^2 + 0.81P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max < 0.001
3375 reflections	Δρmax = 0.78 e Å^−3
174 parameters	Δρmin = −0.72 e Å^−3
1 restraint	Absolute structure: Flack (1983); 1386 Friedel pairs
Primary atom site location: heavy-atom method	Absolute structure parameter: 0.07 (3)

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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) − 0.2580 (0.0164) x − 6.1990 (0.0124) y + 7.2191 (0.0126) z = 2.5049 (0.0092) * −0.0055 (0.0028) C5 * 0.0056 (0.0031) C6 * −0.0014 (0.0034) C7 * −0.0028 (0.0036) C8 * 0.0027 (0.0035) C9 * 0.0014 (0.0031) C10 − 3.1444 (0.0044) Sn1 − 1.3791 (0.0076) C1 − 0.0839 (0.0065) C2 1.0850 (0.0080) C3 − 0.0356 (0.0083) C4 Rms deviation of fitted atoms = 0.0037

1.3243 (0.0158) x − 4.9228 (0.0137) y + 8.0703 (0.0104) z = 0.2309 (0.0109) A ngle to previous plane (with approximate e.s.d.) = 13.97 (0.23) * −0.0108 (0.0027) C11 * 0.0039 (0.0029) C12 * 0.0044 (0.0031) C13 * −0.0057 (0.0031) C14 * −0.0012 (0.0032) C15 * 0.0094 (0.0030) C16 − 0.0399 (0.0061) Sn1 Rms deviation of fitted atoms = 0.0068

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	0.23213 (2)	0.26489 (3)	0.14716 (2)	0.02167 (7)
Cl1	0.12186 (9)	0.28363 (15)	−0.07630 (8)	0.0270 (2)
Cl2	0.14501 (14)	0.48258 (13)	0.24754 (13)	0.0291 (3)
C1	0.1273 (5)	0.0748 (5)	0.2248 (5)	0.0241 (11)
H1A	0.0213	0.0952	0.2256	0.029*
H1B	0.1396	−0.0086	0.1620	0.029*
C2	0.1835 (4)	0.0279 (4)	0.3659 (4)	0.0254 (8)
C3	0.1132 (5)	−0.1180 (5)	0.4000 (5)	0.0400 (11)
H3A	0.1473	−0.1479	0.4920	0.060*
H3B	0.1404	−0.1935	0.3354	0.060*
H3C	0.0067	−0.1068	0.3945	0.060*
C4	0.1358 (6)	0.1413 (6)	0.4682 (5)	0.0468 (13)
H4A	0.0290	0.1402	0.4694	0.070*
H4B	0.1682	0.2396	0.4423	0.070*
H4C	0.1794	0.1167	0.5585	0.070*
C5	0.3506 (4)	0.0110 (4)	0.3682 (4)	0.0223 (8)
C6	0.4077 (5)	−0.0931 (5)	0.2823 (4)	0.0312 (9)
H6	0.3433	−0.1550	0.2287	0.037*
C7	0.5576 (6)	−0.1073 (6)	0.2746 (6)	0.0455 (13)
H7	0.5952	−0.1777	0.2149	0.055*
C8	0.6512 (5)	−0.0201 (8)	0.3526 (6)	0.0604 (18)
H8	0.7538	−0.0300	0.3471	0.072*
C9	0.5979 (6)	0.0812 (7)	0.4384 (6)	0.0576 (17)
H9	0.6634	0.1411	0.4929	0.069*
C10	0.4462 (6)	0.0970 (5)	0.4464 (4)	0.0383 (11)
H10	0.4096	0.1677	0.5064	0.046*
C11	0.4596 (4)	0.3004 (4)	0.1351 (4)	0.0230 (9)
C12	0.5415 (5)	0.2033 (5)	0.0643 (4)	0.0324 (10)
H12	0.4959	0.1196	0.0219	0.039*
C13	0.6890 (5)	0.2268 (5)	0.0544 (5)	0.0390 (13)
H13	0.7446	0.1595	0.0052	0.047*
C14	0.7559 (5)	0.3480 (6)	0.1161 (5)	0.0388 (11)
H14	0.8573	0.3648	0.1085	0.047*
C15	0.6760 (5)	0.4438 (5)	0.1883 (5)	0.0388 (11)
H15	0.7223	0.5270	0.2309	0.047*
C16	0.5270 (5)	0.4204 (5)	0.1997 (4)	0.0325 (10)
H16	0.4722	0.4860	0.2514	0.039*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01552 (11)	0.02109 (12)	0.02812 (12)	0.00006 (13)	−0.00064 (8)	0.00215 (15)
Cl1	0.0185 (4)	0.0364 (7)	0.0254 (3)	0.0037 (5)	−0.0030 (3)	0.0044 (5)
Cl2	0.0270 (6)	0.0207 (5)	0.0397 (6)	0.0026 (4)	0.0040 (5)	−0.0038 (5)
C1	0.013 (2)	0.021 (2)	0.039 (3)	−0.0024 (16)	0.0008 (18)	0.0026 (19)
C2	0.021 (2)	0.019 (2)	0.037 (2)	0.0014 (15)	0.0075 (17)	0.0040 (17)
C3	0.022 (2)	0.034 (2)	0.065 (3)	−0.0011 (18)	0.006 (2)	0.019 (2)
C4	0.058 (3)	0.040 (3)	0.044 (3)	0.018 (2)	0.023 (2)	0.009 (2)
C5	0.0217 (19)	0.022 (2)	0.0235 (17)	−0.0015 (15)	0.0011 (15)	0.0025 (15)
C6	0.026 (2)	0.030 (2)	0.039 (2)	0.0070 (18)	0.0038 (18)	0.0043 (19)
C7	0.034 (3)	0.049 (3)	0.056 (3)	0.020 (2)	0.019 (2)	0.017 (3)
C8	0.018 (2)	0.091 (5)	0.072 (4)	0.004 (3)	−0.002 (3)	0.044 (4)
C9	0.041 (3)	0.075 (4)	0.053 (3)	−0.031 (3)	−0.027 (3)	0.031 (3)
C10	0.046 (3)	0.040 (3)	0.027 (2)	−0.010 (2)	−0.009 (2)	0.0062 (19)
C11	0.0175 (17)	0.027 (3)	0.0240 (16)	−0.0031 (14)	0.0005 (14)	0.0071 (14)
C12	0.023 (2)	0.040 (2)	0.034 (2)	−0.0003 (17)	0.0008 (18)	−0.0017 (18)
C13	0.025 (2)	0.052 (4)	0.041 (2)	0.0100 (19)	0.0057 (19)	0.000 (2)
C14	0.016 (2)	0.059 (3)	0.041 (2)	−0.002 (2)	−0.0014 (19)	0.015 (2)
C15	0.029 (2)	0.044 (3)	0.041 (2)	−0.014 (2)	−0.010 (2)	0.005 (2)
C16	0.028 (2)	0.034 (2)	0.034 (2)	−0.0059 (19)	−0.0021 (19)	0.0016 (19)

Geometric parameters (Å, º)

Sn1—C11	2.121 (4)	C6—H6	0.9500
Sn1—C1	2.141 (5)	C7—C8	1.368 (9)
Sn1—Cl2	2.3727 (12)	C7—H7	0.9500
Sn1—Cl1	2.3740 (8)	C8—C9	1.363 (8)
C1—C2	1.516 (6)	C8—H8	0.9500
C1—H1A	0.9900	C9—C10	1.406 (8)
C1—H1B	0.9900	C9—H9	0.9500
C2—C3	1.520 (6)	C10—H10	0.9500
C2—C4	1.527 (6)	C11—C12	1.379 (6)
C2—C5	1.538 (6)	C11—C16	1.386 (5)
C3—H3A	0.9800	C12—C13	1.379 (6)
C3—H3B	0.9800	C12—H12	0.9500
C3—H3C	0.9800	C13—C14	1.381 (7)
C4—H4A	0.9800	C13—H13	0.9500
C4—H4B	0.9800	C14—C15	1.368 (7)
C4—H4C	0.9800	C14—H14	0.9500
C5—C10	1.372 (6)	C15—C16	1.394 (6)
C5—C6	1.396 (6)	C15—H15	0.9500
C6—C7	1.387 (6)	C16—H16	0.9500
C11—Sn1—C1	127.53 (16)	C7—C6—C5	120.7 (4)
C11—Sn1—Cl2	104.91 (10)	C7—C6—H6	119.7
C1—Sn1—Cl2	110.36 (13)	C5—C6—H6	119.7
C11—Sn1—Cl1	107.15 (10)	C8—C7—C6	120.1 (5)
C1—Sn1—Cl1	102.62 (14)	C8—C7—H7	120.0
Cl2—Sn1—Cl1	101.31 (5)	C6—C7—H7	120.0
C2—C1—Sn1	115.0 (3)	C9—C8—C7	120.3 (5)
C2—C1—H1A	108.5	C9—C8—H8	119.9
Sn1—C1—H1A	108.5	C7—C8—H8	119.9
C2—C1—H1B	108.5	C8—C9—C10	120.1 (5)
Sn1—C1—H1B	108.5	C8—C9—H9	120.0
H1A—C1—H1B	107.5	C10—C9—H9	120.0
C1—C2—C3	109.0 (4)	C5—C10—C9	120.4 (5)
C1—C2—C4	109.1 (4)	C5—C10—H10	119.8
C3—C2—C4	107.1 (4)	C9—C10—H10	119.8
C1—C2—C5	108.5 (3)	C12—C11—C16	119.7 (4)
C3—C2—C5	110.3 (3)	C12—C11—Sn1	120.2 (3)
C4—C2—C5	112.8 (4)	C16—C11—Sn1	120.1 (3)
C2—C3—H3A	109.5	C11—C12—C13	120.5 (4)
C2—C3—H3B	109.5	C11—C12—H12	119.7
H3A—C3—H3B	109.5	C13—C12—H12	119.7
C2—C3—H3C	109.5	C12—C13—C14	120.0 (4)
H3A—C3—H3C	109.5	C12—C13—H13	120.0
H3B—C3—H3C	109.5	C14—C13—H13	120.0
C2—C4—H4A	109.5	C15—C14—C13	120.0 (4)
C2—C4—H4B	109.5	C15—C14—H14	120.0
H4A—C4—H4B	109.5	C13—C14—H14	120.0
C2—C4—H4C	109.5	C14—C15—C16	120.5 (4)
H4A—C4—H4C	109.5	C14—C15—H15	119.8
H4B—C4—H4C	109.5	C16—C15—H15	119.8
C10—C5—C6	118.4 (4)	C11—C16—C15	119.4 (4)
C10—C5—C2	123.3 (4)	C11—C16—H16	120.3
C6—C5—C2	118.2 (3)	C15—C16—H16	120.3
C11—Sn1—C1—C2	52.5 (4)	C6—C5—C10—C9	0.8 (6)
Cl2—Sn1—C1—C2	−76.7 (3)	C2—C5—C10—C9	−176.6 (4)
Cl1—Sn1—C1—C2	176.1 (3)	C8—C9—C10—C5	0.0 (7)
Sn1—C1—C2—C3	−172.9 (3)	C1—Sn1—C11—C12	57.8 (4)
Sn1—C1—C2—C4	70.4 (4)	Cl2—Sn1—C11—C12	−171.0 (3)
Sn1—C1—C2—C5	−52.8 (4)	Cl1—Sn1—C11—C12	−63.9 (3)
C1—C2—C5—C10	116.2 (4)	C1—Sn1—C11—C16	−121.4 (3)
C3—C2—C5—C10	−124.5 (4)	Cl2—Sn1—C11—C16	9.8 (3)
C4—C2—C5—C10	−4.8 (5)	Cl1—Sn1—C11—C16	116.9 (3)
C1—C2—C5—C6	−61.2 (4)	C16—C11—C12—C13	−1.7 (6)
C3—C2—C5—C6	58.2 (5)	Sn1—C11—C12—C13	179.1 (3)
C4—C2—C5—C6	177.9 (4)	C11—C12—C13—C14	0.2 (7)
C10—C5—C6—C7	−1.2 (6)	C12—C13—C14—C15	0.7 (7)
C2—C5—C6—C7	176.3 (4)	C13—C14—C15—C16	−0.2 (7)
C5—C6—C7—C8	0.8 (7)	C12—C11—C16—C15	2.2 (6)
C6—C7—C8—C9	0.0 (8)	Sn1—C11—C16—C15	−178.6 (3)
C7—C8—C9—C10	−0.4 (8)	C14—C15—C16—C11	−1.2 (7)

(II) Dibromo(2-methyl-2-phenylpropyl)phenylstannane

Crystal data

[SnBr2(C6H5)(C10H13)]	F(000) = 468
Mr = 488.81	Dx = 1.925 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7897 reflections
a = 9.2966 (3) Å	θ = 2.9–27.5°
b = 9.3763 (3) Å	µ = 6.24 mm^−1
c = 9.6898 (3) Å	T = 120 K
β = 93.010 (2)°	Slab, colourless
V = 843.47 (5) Å^3	0.30 × 0.18 × 0.08 mm
Z = 2

Data collection

Enraf Nonius KappaCCD area detector diffractometer	3772 independent reflections
Radiation source: Enraf Nonius FR591 rotating anode	3618 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
Detector resolution: 9.091 pixels mm^-1	θmax = 27.5°, θmin = 3.0°
ϕ and ω scans to fill the Ewald sphere	h = −12→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997)	k = −12→11
Tmin = 0.528, Tmax = 0.861	l = −12→12
9872 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)] = 0.026	H-atom parameters constrained
wR(F^2) = 0.061	w = 1/[σ^2(Fo^2) + (0.0343P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.08	(Δ/σ)max = 0.001
3772 reflections	Δρmax = 0.37 e Å^−3
174 parameters	Δρmin = −1.27 e Å^−3
1 restraint	Absolute structure: (Flack, 1983; 1735 Friedel pairs)
Primary atom site location: heavy-atom method	Absolute structure parameter: 0.006 (7)

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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.1145 (0.0159) x + 6.2483 (0.0126) y − 7.2201 (0.0117) z = 1.6849 (0.0210) * −0.0068 (0.0027) C5 * 0.0083 (0.0029) C6 * −0.0020 (0.0033) C7 * −0.0058 (0.0033) C8 * 0.0070 (0.0030) C9 * −0.0008 (0.0028) C10 − 3.1534 (0.0043) Sn1 − 1.3928 (0.0068) C1 − 0.0784 (0.0061) C2 1.0786 (0.0073) C3 − 0.0073 (0.0078) C4 Rms deviation of fitted atoms = 0.0058

1.3529 (0.0154) x − 5.3677 (0.0143) y + 7.7339 (0.0110) z = 3.6651 (0.0194) A ngle to previous plane (with approximate e.s.d.) = 11.11 (0.24) * 0.0115 (0.0028) C11 * −0.0010 (0.0030) C12 * −0.0077 (0.0032) C13 * 0.0059 (0.0032) C14 * 0.0047 (0.0032) C15 * −0.0133 (0.0029) C16 0.0183 (0.0058) Sn1 Rms deviation of fitted atoms = 0.0084

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	0.76993 (2)	0.735210 (18)	0.85186 (2)	0.02404 (7)
Br1	0.88162 (4)	0.72228 (5)	1.09150 (3)	0.03338 (10)
Br2	0.86195 (4)	0.51400 (4)	0.74505 (4)	0.03449 (10)
C1	0.8730 (4)	0.9194 (4)	0.7690 (4)	0.0278 (8)
H1A	0.8614	1.0006	0.8328	0.033*
H1B	0.9774	0.8997	0.7658	0.033*
C2	0.8149 (4)	0.9634 (4)	0.6242 (4)	0.0275 (7)
C3	0.8846 (5)	1.1056 (4)	0.5881 (5)	0.0368 (9)
H3A	0.8442	1.1389	0.4983	0.055*
H3B	0.9888	1.0926	0.5835	0.055*
H3C	0.8653	1.1763	0.6592	0.055*
C4	0.8641 (5)	0.8535 (4)	0.5199 (4)	0.0410 (10)
H4A	0.9696	0.8500	0.5234	0.062*
H4B	0.8281	0.8806	0.4268	0.062*
H4C	0.8263	0.7594	0.5429	0.062*
C5	0.6525 (4)	0.9782 (4)	0.6244 (3)	0.0263 (7)
C6	0.5919 (5)	1.0792 (4)	0.7088 (4)	0.0346 (9)
H6	0.6536	1.1418	0.7614	0.042*
C7	0.4448 (5)	1.0914 (6)	0.7185 (5)	0.0522 (13)
H7	0.4064	1.1604	0.7782	0.063*
C8	0.3544 (5)	1.0033 (7)	0.6413 (5)	0.0577 (14)
H8	0.2532	1.0112	0.6481	0.069*
C9	0.4094 (5)	0.9037 (6)	0.5542 (5)	0.0513 (13)
H9	0.3462	0.8442	0.4997	0.062*
C10	0.5585 (5)	0.8903 (5)	0.5461 (4)	0.0389 (9)
H10	0.5963	0.8207	0.4866	0.047*
C11	0.5455 (4)	0.7022 (4)	0.8673 (4)	0.0277 (8)
C12	0.4675 (4)	0.7963 (5)	0.9446 (4)	0.0366 (9)
H12	0.5140	0.8746	0.9904	0.044*
C13	0.3199 (4)	0.7747 (6)	0.9547 (5)	0.0456 (12)
H13	0.2659	0.8392	1.0070	0.055*
C14	0.2526 (5)	0.6624 (5)	0.8902 (5)	0.0431 (10)
H14	0.1523	0.6482	0.8992	0.052*
C15	0.3294 (5)	0.5684 (5)	0.8114 (5)	0.0421 (10)
H15	0.2824	0.4899	0.7666	0.051*
C16	0.4765 (4)	0.5907 (4)	0.7988 (4)	0.0347 (9)
H16	0.5293	0.5287	0.7427	0.042*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sn1	0.01824 (12)	0.02568 (11)	0.02818 (11)	−0.00088 (10)	0.00118 (8)	0.00219 (10)
Br1	0.02490 (18)	0.0442 (2)	0.03059 (17)	0.00090 (18)	−0.00303 (13)	0.00279 (18)
Br2	0.0331 (2)	0.02855 (18)	0.0423 (2)	0.00375 (16)	0.00686 (16)	−0.00133 (17)
C1	0.0193 (18)	0.0272 (18)	0.036 (2)	−0.0013 (14)	−0.0026 (15)	−0.0014 (15)
C2	0.0249 (19)	0.0249 (16)	0.0331 (18)	0.0012 (14)	0.0044 (14)	0.0024 (15)
C3	0.029 (2)	0.033 (2)	0.049 (2)	−0.0028 (16)	0.0046 (18)	0.0111 (19)
C4	0.053 (3)	0.034 (2)	0.038 (2)	0.0122 (19)	0.017 (2)	0.0054 (18)
C5	0.0248 (18)	0.0249 (17)	0.0292 (17)	−0.0035 (13)	0.0008 (14)	0.0032 (14)
C6	0.027 (2)	0.040 (2)	0.037 (2)	0.0033 (16)	0.0030 (16)	0.0006 (17)
C7	0.031 (3)	0.068 (3)	0.060 (3)	0.017 (2)	0.017 (2)	0.016 (3)
C8	0.027 (2)	0.082 (4)	0.064 (3)	0.005 (2)	0.003 (2)	0.035 (3)
C9	0.035 (3)	0.063 (3)	0.053 (3)	−0.020 (2)	−0.019 (2)	0.023 (2)
C10	0.041 (2)	0.041 (2)	0.034 (2)	−0.0105 (19)	−0.0079 (17)	0.0080 (18)
C11	0.0190 (17)	0.036 (2)	0.0285 (16)	0.0023 (13)	0.0017 (13)	0.0042 (14)
C12	0.025 (2)	0.046 (2)	0.038 (2)	0.0004 (17)	0.0010 (16)	−0.0067 (18)
C13	0.025 (2)	0.065 (3)	0.048 (2)	0.0081 (18)	0.0088 (18)	0.001 (2)
C14	0.019 (2)	0.066 (3)	0.044 (2)	−0.0019 (19)	−0.0018 (17)	0.014 (2)
C15	0.031 (2)	0.048 (2)	0.046 (2)	−0.0130 (19)	−0.0065 (18)	0.003 (2)
C16	0.024 (2)	0.038 (2)	0.042 (2)	−0.0044 (16)	0.0003 (16)	−0.0021 (17)

Geometric parameters (Å, º)

Sn1—C11	2.122 (3)	C6—H6	0.9500
Sn1—C1	2.151 (4)	C7—C8	1.371 (8)
Sn1—Br2	2.4895 (4)	C7—H7	0.9500
Sn1—Br1	2.4963 (4)	C8—C9	1.375 (8)
C1—C2	1.534 (5)	C8—H8	0.9500
C1—H1A	0.9900	C9—C10	1.399 (7)
C1—H1B	0.9900	C9—H9	0.9500
C2—C5	1.517 (5)	C10—H10	0.9500
C2—C4	1.530 (5)	C11—C16	1.379 (5)
C2—C3	1.531 (5)	C11—C12	1.386 (5)
C3—H3A	0.9800	C12—C13	1.395 (6)
C3—H3B	0.9800	C12—H12	0.9500
C3—H3C	0.9800	C13—C14	1.360 (7)
C4—H4A	0.9800	C13—H13	0.9500
C4—H4B	0.9800	C14—C15	1.388 (7)
C4—H4C	0.9800	C14—H14	0.9500
C5—C6	1.389 (5)	C15—C16	1.394 (6)
C5—C10	1.396 (5)	C15—H15	0.9500
C6—C7	1.381 (6)	C16—H16	0.9500
C11—Sn1—C1	127.04 (14)	C7—C6—C5	122.0 (4)
C11—Sn1—Br2	105.57 (10)	C7—C6—H6	119.0
C1—Sn1—Br2	110.13 (10)	C5—C6—H6	119.0
C11—Sn1—Br1	106.84 (9)	C8—C7—C6	119.6 (5)
C1—Sn1—Br1	102.38 (10)	C8—C7—H7	120.2
Br2—Sn1—Br1	102.183 (15)	C6—C7—H7	120.2
C2—C1—Sn1	114.5 (3)	C7—C8—C9	120.5 (4)
C2—C1—H1A	108.6	C7—C8—H8	119.8
Sn1—C1—H1A	108.6	C9—C8—H8	119.8
C2—C1—H1B	108.6	C8—C9—C10	119.8 (5)
Sn1—C1—H1B	108.6	C8—C9—H9	120.1
H1A—C1—H1B	107.6	C10—C9—H9	120.1
C5—C2—C4	113.3 (3)	C5—C10—C9	120.7 (4)
C5—C2—C3	110.7 (3)	C5—C10—H10	119.6
C4—C2—C3	106.9 (3)	C9—C10—H10	119.6
C5—C2—C1	109.0 (3)	C16—C11—C12	119.9 (4)
C4—C2—C1	108.6 (3)	C16—C11—Sn1	120.7 (3)
C3—C2—C1	108.1 (3)	C12—C11—Sn1	119.3 (3)
C2—C3—H3A	109.5	C11—C12—C13	119.4 (4)
C2—C3—H3B	109.5	C11—C12—H12	120.3
H3A—C3—H3B	109.5	C13—C12—H12	120.3
C2—C3—H3C	109.5	C14—C13—C12	120.7 (4)
H3A—C3—H3C	109.5	C14—C13—H13	119.6
H3B—C3—H3C	109.5	C12—C13—H13	119.6
C2—C4—H4A	109.5	C13—C14—C15	120.4 (4)
C2—C4—H4B	109.5	C13—C14—H14	119.8
H4A—C4—H4B	109.5	C15—C14—H14	119.8
C2—C4—H4C	109.5	C14—C15—C16	119.2 (4)
H4A—C4—H4C	109.5	C14—C15—H15	120.4
H4B—C4—H4C	109.5	C16—C15—H15	120.4
C6—C5—C10	117.4 (4)	C11—C16—C15	120.3 (4)
C6—C5—C2	119.9 (3)	C11—C16—H16	119.8
C10—C5—C2	122.7 (3)	C15—C16—H16	119.8
C11—Sn1—C1—C2	−52.1 (3)	C6—C5—C10—C9	−0.6 (6)
Br2—Sn1—C1—C2	77.3 (3)	C2—C5—C10—C9	177.2 (4)
Br1—Sn1—C1—C2	−174.6 (2)	C8—C9—C10—C5	−0.7 (6)
Sn1—C1—C2—C5	52.3 (3)	C1—Sn1—C11—C16	118.4 (3)
Sn1—C1—C2—C4	−71.5 (4)	Br2—Sn1—C11—C16	−12.7 (3)
Sn1—C1—C2—C3	172.8 (2)	Br1—Sn1—C11—C16	−121.0 (3)
C4—C2—C5—C6	−176.8 (3)	C1—Sn1—C11—C12	−60.0 (4)
C3—C2—C5—C6	−56.6 (4)	Br2—Sn1—C11—C12	168.9 (3)
C1—C2—C5—C6	62.2 (4)	Br1—Sn1—C11—C12	60.6 (3)
C4—C2—C5—C10	5.5 (5)	C16—C11—C12—C13	1.5 (6)
C3—C2—C5—C10	125.6 (4)	Sn1—C11—C12—C13	179.9 (3)
C1—C2—C5—C10	−115.6 (4)	C11—C12—C13—C14	0.4 (7)
C10—C5—C6—C7	1.5 (6)	C12—C13—C14—C15	−1.1 (7)
C2—C5—C6—C7	−176.3 (4)	C13—C14—C15—C16	−0.1 (7)
C5—C6—C7—C8	−1.1 (7)	C12—C11—C16—C15	−2.6 (6)
C6—C7—C8—C9	−0.3 (7)	Sn1—C11—C16—C15	178.9 (3)
C7—C8—C9—C10	1.2 (7)	C14—C15—C16—C11	2.0 (7)