Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803018439/tk6129sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803018439/tk6129Isup2.hkl |
CCDC reference: 222823
The title compound was prepared as described by Wharf & Simard (1997). Suitable crystals were obtained from recrystallization of an acetone solution of the compound.
H atoms were constrained to the parent site using a riding model, with C—H distances of 0.93 Å and Uiso(H) values of 1.2Ueq(parent atom).
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1985)'; cell refinement: MSC/AFC Diffractometer Control Software; data reduction: DARTD2 in NRCVAX (Gabe et al., 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL96 (Sheldrick, 1996); molecular graphics: ORTEPII (Johnson, 1976) in NRCVAX; software used to prepare material for publication: NRCVAX and SHELXL96.
Fig. 1. ORTEP (SHELXTL, 1997) drawing of (I). Displacement ellipsoids correspond to 30% probability. | |
Fig. 2. Packing diagram for (I), viewed along the b axis. H atoms have been omitted for clarity. |
C24H12Cl8Sn | F(000) = 2736 |
Mr = 702.63 | Dx = 1.766 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C2yc | Cell parameters from 25 reflections |
a = 24.861 (8) Å | θ = 12.5–15.5° |
b = 11.908 (3) Å | µ = 1.79 mm−1 |
c = 18.139 (4) Å | T = 293 K |
β = 100.16 (2)° | Irregular shape, colourless |
V = 5286 (2) Å3 | 0.55 × 0.47 × 0.45 mm |
Z = 8 |
Rigaku AFC6S diffractometer | 3632 reflections with I > 2σ(I) |
Radiation source: Sealed tube | Rint = 0.099 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ω/2θ scans | h = −31→31 |
Absorption correction: ψ scan (ABSN in NRCVAX; Gabe et al, 1989) | k = −15→15 |
Tmin = 0.354, Tmax = 0.449 | l = −22→22 |
19754 measured reflections | 3 standard reflections every 250 reflections |
5195 independent reflections | intensity decay: 2.3% |
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)] = 0.050 | H-atom parameters constrained |
wR(F2) = 0.123 | w = 1/[σ2(Fo2) + (0.0767P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
5195 reflections | Δρmax = 0.70 e Å−3 |
299 parameters | Δρmin = −0.94 e Å−3 |
0 restraints | Extinction correction: SHELXL96, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00069 (9) |
C24H12Cl8Sn | V = 5286 (2) Å3 |
Mr = 702.63 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 24.861 (8) Å | µ = 1.79 mm−1 |
b = 11.908 (3) Å | T = 293 K |
c = 18.139 (4) Å | 0.55 × 0.47 × 0.45 mm |
β = 100.16 (2)° |
Rigaku AFC6S diffractometer | 3632 reflections with I > 2σ(I) |
Absorption correction: ψ scan (ABSN in NRCVAX; Gabe et al, 1989) | Rint = 0.099 |
Tmin = 0.354, Tmax = 0.449 | 3 standard reflections every 250 reflections |
19754 measured reflections | intensity decay: 2.3% |
5195 independent reflections |
R[F2 > 2σ(F2)] = 0.050 | 0 restraints |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.70 e Å−3 |
5195 reflections | Δρmin = −0.94 e Å−3 |
299 parameters |
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. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R-factor_obs 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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.883604 (16) | 0.13574 (3) | 0.15916 (2) | 0.04155 (17) | |
Cl1 | 0.77220 (10) | 0.17261 (18) | 0.41056 (14) | 0.0900 (7) | |
Cl2 | 0.82029 (9) | 0.55295 (15) | 0.27881 (12) | 0.0789 (6) | |
Cl3 | 1.02826 (11) | 0.50289 (18) | 0.1122 (2) | 0.1204 (11) | |
Cl4 | 1.07935 (8) | 0.08600 (17) | 0.03834 (11) | 0.0697 (5) | |
Cl5 | 0.97003 (8) | −0.19490 (17) | 0.38142 (11) | 0.0728 (5) | |
Cl6 | 0.88133 (9) | −0.34074 (16) | 0.10667 (12) | 0.0777 (6) | |
Cl7 | 0.81048 (9) | 0.14844 (19) | −0.16107 (11) | 0.0788 (6) | |
Cl8 | 0.66112 (7) | 0.06735 (16) | 0.01098 (11) | 0.0664 (5) | |
C11 | 0.8521 (2) | 0.2317 (5) | 0.2415 (3) | 0.0442 (14) | |
C12 | 0.8269 (3) | 0.1779 (6) | 0.2943 (4) | 0.0536 (16) | |
H12 | 0.8268 | 0.0999 | 0.2965 | 0.064* | |
C13 | 0.8021 (2) | 0.2396 (6) | 0.3437 (4) | 0.0515 (16) | |
C14 | 0.7998 (3) | 0.3558 (5) | 0.3397 (4) | 0.0529 (16) | |
H14 | 0.7820 | 0.3970 | 0.3716 | 0.063* | |
C15 | 0.8246 (3) | 0.4082 (5) | 0.2874 (4) | 0.0504 (15) | |
C16 | 0.8512 (2) | 0.3482 (5) | 0.2389 (3) | 0.0462 (14) | |
H16 | 0.8684 | 0.3860 | 0.2047 | 0.055* | |
C21 | 0.9551 (2) | 0.2063 (5) | 0.1273 (3) | 0.0434 (14) | |
C22 | 0.9681 (3) | 0.3209 (6) | 0.1332 (5) | 0.064 (2) | |
H22 | 0.9459 | 0.3704 | 0.1540 | 0.077* | |
C23 | 1.0140 (3) | 0.3600 (5) | 0.1081 (5) | 0.069 (2) | |
C24 | 1.0478 (3) | 0.2898 (6) | 0.0777 (4) | 0.0601 (18) | |
H24 | 1.0782 | 0.3176 | 0.0603 | 0.072* | |
C25 | 1.0357 (2) | 0.1779 (5) | 0.0736 (4) | 0.0476 (15) | |
C26 | 0.9901 (2) | 0.1353 (5) | 0.0984 (3) | 0.0416 (13) | |
H26 | 0.9831 | 0.0586 | 0.0955 | 0.050* | |
C31 | 0.8998 (2) | −0.0331 (5) | 0.1958 (4) | 0.0458 (14) | |
C32 | 0.9270 (2) | −0.0570 (5) | 0.2687 (4) | 0.0471 (15) | |
H32 | 0.9375 | 0.0010 | 0.3025 | 0.057* | |
C33 | 0.9381 (3) | −0.1664 (5) | 0.2895 (4) | 0.0495 (15) | |
C34 | 0.9244 (2) | −0.2550 (5) | 0.2424 (4) | 0.0501 (16) | |
H34 | 0.9321 | −0.3286 | 0.2579 | 0.060* | |
C35 | 0.8984 (3) | −0.2305 (5) | 0.1705 (4) | 0.0543 (17) | |
C36 | 0.8843 (2) | −0.1219 (5) | 0.1468 (3) | 0.0485 (15) | |
H36 | 0.8648 | −0.1086 | 0.0990 | 0.058* | |
C41 | 0.8224 (2) | 0.1255 (4) | 0.0607 (3) | 0.0407 (13) | |
C42 | 0.7682 (2) | 0.1035 (5) | 0.0675 (3) | 0.0440 (14) | |
H42 | 0.7588 | 0.0959 | 0.1146 | 0.053* | |
C43 | 0.7290 (2) | 0.0930 (5) | 0.0043 (4) | 0.0457 (14) | |
C44 | 0.7415 (3) | 0.1043 (5) | −0.0661 (4) | 0.0532 (16) | |
H44 | 0.7149 | 0.0957 | −0.1087 | 0.064* | |
C45 | 0.7954 (3) | 0.1291 (5) | −0.0717 (3) | 0.0513 (16) | |
C46 | 0.8354 (2) | 0.1384 (5) | −0.0096 (3) | 0.0439 (14) | |
H46 | 0.8713 | 0.1532 | −0.0149 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.0399 (2) | 0.0394 (2) | 0.0458 (3) | 0.00261 (18) | 0.00886 (17) | −0.00493 (19) |
Cl1 | 0.1108 (18) | 0.0703 (13) | 0.1079 (18) | −0.0104 (12) | 0.0715 (15) | 0.0044 (12) |
Cl2 | 0.1084 (16) | 0.0439 (9) | 0.0967 (15) | 0.0166 (10) | 0.0515 (13) | 0.0073 (9) |
Cl3 | 0.0983 (18) | 0.0484 (12) | 0.224 (3) | −0.0214 (11) | 0.054 (2) | −0.0187 (15) |
Cl4 | 0.0636 (11) | 0.0769 (12) | 0.0750 (12) | 0.0067 (9) | 0.0296 (9) | −0.0139 (10) |
Cl5 | 0.0791 (13) | 0.0694 (12) | 0.0633 (12) | 0.0118 (10) | −0.0056 (10) | 0.0110 (10) |
Cl6 | 0.1018 (16) | 0.0541 (11) | 0.0793 (14) | −0.0082 (10) | 0.0216 (12) | −0.0227 (9) |
Cl7 | 0.0880 (14) | 0.1046 (16) | 0.0475 (10) | 0.0097 (12) | 0.0222 (9) | 0.0052 (10) |
Cl8 | 0.0422 (9) | 0.0668 (12) | 0.0883 (13) | −0.0105 (8) | 0.0062 (9) | −0.0033 (10) |
C11 | 0.039 (3) | 0.046 (3) | 0.047 (4) | 0.006 (3) | 0.009 (3) | −0.008 (3) |
C12 | 0.049 (4) | 0.052 (4) | 0.060 (4) | −0.006 (3) | 0.010 (3) | −0.012 (3) |
C13 | 0.049 (4) | 0.057 (4) | 0.053 (4) | −0.005 (3) | 0.021 (3) | −0.005 (3) |
C14 | 0.054 (4) | 0.051 (4) | 0.060 (4) | 0.006 (3) | 0.027 (3) | −0.006 (3) |
C15 | 0.053 (4) | 0.043 (3) | 0.056 (4) | 0.008 (3) | 0.012 (3) | 0.003 (3) |
C16 | 0.048 (3) | 0.048 (4) | 0.044 (3) | 0.007 (3) | 0.012 (3) | −0.001 (3) |
C21 | 0.039 (3) | 0.042 (3) | 0.050 (4) | 0.004 (3) | 0.009 (3) | 0.002 (3) |
C22 | 0.051 (4) | 0.045 (4) | 0.099 (6) | 0.005 (3) | 0.017 (4) | −0.010 (4) |
C23 | 0.054 (4) | 0.038 (3) | 0.118 (7) | −0.010 (3) | 0.020 (4) | −0.001 (4) |
C24 | 0.041 (4) | 0.064 (4) | 0.077 (5) | −0.007 (3) | 0.015 (3) | −0.004 (4) |
C25 | 0.040 (3) | 0.052 (4) | 0.051 (4) | 0.004 (3) | 0.009 (3) | −0.005 (3) |
C26 | 0.045 (3) | 0.041 (3) | 0.037 (3) | 0.005 (3) | −0.001 (2) | −0.003 (3) |
C31 | 0.040 (3) | 0.045 (3) | 0.056 (4) | 0.003 (3) | 0.017 (3) | 0.001 (3) |
C32 | 0.045 (3) | 0.041 (3) | 0.055 (4) | −0.001 (3) | 0.010 (3) | −0.003 (3) |
C33 | 0.045 (3) | 0.055 (4) | 0.049 (4) | 0.004 (3) | 0.012 (3) | 0.001 (3) |
C34 | 0.051 (4) | 0.044 (4) | 0.058 (4) | 0.000 (3) | 0.018 (3) | 0.008 (3) |
C35 | 0.064 (4) | 0.041 (3) | 0.064 (5) | −0.007 (3) | 0.028 (4) | −0.013 (3) |
C36 | 0.056 (4) | 0.046 (4) | 0.046 (4) | 0.007 (3) | 0.019 (3) | 0.002 (3) |
C41 | 0.044 (3) | 0.034 (3) | 0.046 (3) | 0.006 (3) | 0.010 (3) | 0.003 (3) |
C42 | 0.050 (4) | 0.035 (3) | 0.047 (4) | −0.002 (3) | 0.009 (3) | 0.001 (3) |
C43 | 0.044 (3) | 0.032 (3) | 0.063 (4) | −0.003 (3) | 0.013 (3) | −0.002 (3) |
C44 | 0.053 (4) | 0.040 (3) | 0.063 (4) | 0.006 (3) | 0.000 (3) | −0.006 (3) |
C45 | 0.067 (4) | 0.048 (4) | 0.042 (3) | 0.012 (3) | 0.016 (3) | −0.002 (3) |
C46 | 0.041 (3) | 0.036 (3) | 0.054 (4) | 0.005 (3) | 0.007 (3) | −0.006 (3) |
Sn1—C31 | 2.134 (6) | C22—H22 | 0.9300 |
Sn1—C11 | 2.135 (5) | C23—C24 | 1.368 (10) |
Sn1—C41 | 2.135 (6) | C24—C25 | 1.365 (9) |
Sn1—C21 | 2.135 (6) | C24—H24 | 0.9300 |
Cl1—C13 | 1.725 (6) | C25—C26 | 1.387 (8) |
Cl2—C15 | 1.733 (7) | C26—H26 | 0.9300 |
Cl3—C23 | 1.737 (7) | C31—C36 | 1.391 (8) |
Cl4—C25 | 1.740 (6) | C31—C32 | 1.403 (9) |
Cl5—C33 | 1.750 (7) | C32—C33 | 1.371 (9) |
Cl6—C35 | 1.752 (6) | C32—H32 | 0.9300 |
Cl7—C45 | 1.741 (6) | C33—C34 | 1.362 (9) |
Cl8—C43 | 1.741 (6) | C34—C35 | 1.381 (9) |
C11—C16 | 1.388 (8) | C34—H34 | 0.9300 |
C11—C12 | 1.391 (8) | C35—C36 | 1.388 (9) |
C12—C13 | 1.385 (8) | C36—H36 | 0.9300 |
C12—H12 | 0.9300 | C41—C46 | 1.380 (8) |
C13—C14 | 1.386 (8) | C41—C42 | 1.399 (8) |
C14—C15 | 1.370 (9) | C42—C43 | 1.372 (8) |
C14—H14 | 0.9300 | C42—H42 | 0.9300 |
C15—C16 | 1.386 (8) | C43—C44 | 1.374 (9) |
C16—H16 | 0.9300 | C44—C45 | 1.393 (9) |
C21—C26 | 1.383 (8) | C44—H44 | 0.9300 |
C21—C22 | 1.402 (9) | C45—C46 | 1.368 (9) |
C22—C23 | 1.383 (9) | C46—H46 | 0.9300 |
C31—Sn1—C11 | 111.0 (2) | C21—C26—C25 | 120.4 (6) |
C31—Sn1—C41 | 105.9 (2) | C21—C26—H26 | 119.8 |
C11—Sn1—C41 | 108.7 (2) | C25—C26—H26 | 119.8 |
C31—Sn1—C21 | 109.6 (2) | C36—C31—C32 | 118.8 (6) |
C11—Sn1—C21 | 113.8 (2) | C36—C31—Sn1 | 120.1 (5) |
C41—Sn1—C21 | 107.5 (2) | C32—C31—Sn1 | 121.1 (4) |
C16—C11—C12 | 118.4 (5) | C33—C32—C31 | 119.4 (6) |
C16—C11—Sn1 | 121.2 (4) | C33—C32—H32 | 120.3 |
C12—C11—Sn1 | 120.0 (4) | C31—C32—H32 | 120.3 |
C13—C12—C11 | 120.5 (6) | C34—C33—C32 | 123.2 (6) |
C13—C12—H12 | 119.7 | C34—C33—Cl5 | 118.0 (5) |
C11—C12—H12 | 119.7 | C32—C33—Cl5 | 118.8 (5) |
C12—C13—C14 | 120.9 (6) | C33—C34—C35 | 116.9 (6) |
C12—C13—Cl1 | 120.4 (5) | C33—C34—H34 | 121.6 |
C14—C13—Cl1 | 118.7 (5) | C35—C34—H34 | 121.6 |
C15—C14—C13 | 118.2 (6) | C34—C35—C36 | 122.6 (6) |
C15—C14—H14 | 120.9 | C34—C35—Cl6 | 118.9 (5) |
C13—C14—H14 | 120.9 | C36—C35—Cl6 | 118.4 (6) |
C14—C15—C16 | 121.8 (6) | C35—C36—C31 | 118.9 (6) |
C14—C15—Cl2 | 119.1 (5) | C35—C36—H36 | 120.5 |
C16—C15—Cl2 | 119.0 (5) | C31—C36—H36 | 120.5 |
C15—C16—C11 | 120.1 (6) | C46—C41—C42 | 119.3 (5) |
C15—C16—H16 | 120.0 | C46—C41—Sn1 | 121.2 (4) |
C11—C16—H16 | 120.0 | C42—C41—Sn1 | 119.5 (4) |
C26—C21—C22 | 118.2 (6) | C43—C42—C41 | 119.7 (6) |
C26—C21—Sn1 | 118.2 (4) | C43—C42—H42 | 120.1 |
C22—C21—Sn1 | 123.6 (5) | C41—C42—H42 | 120.1 |
C23—C22—C21 | 119.6 (6) | C42—C43—C44 | 121.6 (6) |
C23—C22—H22 | 120.2 | C42—C43—Cl8 | 120.8 (5) |
C21—C22—H22 | 120.2 | C44—C43—Cl8 | 117.6 (5) |
C24—C23—C22 | 121.9 (6) | C43—C44—C45 | 117.8 (6) |
C24—C23—Cl3 | 118.8 (6) | C43—C44—H44 | 121.1 |
C22—C23—Cl3 | 119.3 (6) | C45—C44—H44 | 121.1 |
C25—C24—C23 | 118.4 (6) | C46—C45—C44 | 121.7 (6) |
C25—C24—H24 | 120.8 | C46—C45—Cl7 | 120.8 (5) |
C23—C24—H24 | 120.8 | C44—C45—Cl7 | 117.6 (5) |
C24—C25—C26 | 121.5 (6) | C45—C46—C41 | 119.8 (6) |
C24—C25—Cl4 | 119.3 (5) | C45—C46—H46 | 120.1 |
C26—C25—Cl4 | 119.1 (5) | C41—C46—H46 | 120.1 |
C31—Sn1—C11—C16 | 164.0 (5) | C11—Sn1—C31—C36 | 135.8 (5) |
C41—Sn1—C11—C16 | −79.9 (5) | C41—Sn1—C31—C36 | 18.0 (5) |
C21—Sn1—C11—C16 | 39.8 (6) | C21—Sn1—C31—C36 | −97.6 (5) |
C31—Sn1—C11—C12 | −22.7 (6) | C11—Sn1—C31—C32 | −45.4 (5) |
C41—Sn1—C11—C12 | 93.4 (5) | C41—Sn1—C31—C32 | −163.2 (5) |
C21—Sn1—C11—C12 | −146.9 (5) | C21—Sn1—C31—C32 | 81.1 (5) |
C16—C11—C12—C13 | −0.7 (9) | C36—C31—C32—C33 | 0.6 (9) |
Sn1—C11—C12—C13 | −174.2 (5) | Sn1—C31—C32—C33 | −178.1 (4) |
C11—C12—C13—C14 | 2.6 (10) | C31—C32—C33—C34 | 0.6 (9) |
C11—C12—C13—Cl1 | −178.5 (5) | C31—C32—C33—Cl5 | −177.9 (5) |
C12—C13—C14—C15 | −2.4 (10) | C32—C33—C34—C35 | 0.4 (10) |
Cl1—C13—C14—C15 | 178.7 (5) | Cl5—C33—C34—C35 | 179.0 (5) |
C13—C14—C15—C16 | 0.4 (10) | C33—C34—C35—C36 | −2.8 (9) |
C13—C14—C15—Cl2 | 177.6 (5) | C33—C34—C35—Cl6 | 178.4 (5) |
C14—C15—C16—C11 | 1.4 (10) | C34—C35—C36—C31 | 4.0 (9) |
Cl2—C15—C16—C11 | −175.8 (5) | Cl6—C35—C36—C31 | −177.1 (5) |
C12—C11—C16—C15 | −1.2 (9) | C32—C31—C36—C35 | −2.8 (9) |
Sn1—C11—C16—C15 | 172.2 (5) | Sn1—C31—C36—C35 | 175.9 (4) |
C31—Sn1—C21—C26 | 30.8 (5) | C31—Sn1—C41—C46 | −103.2 (5) |
C11—Sn1—C21—C26 | 155.8 (4) | C11—Sn1—C41—C46 | 137.4 (4) |
C41—Sn1—C21—C26 | −83.8 (5) | C21—Sn1—C41—C46 | 13.8 (5) |
C31—Sn1—C21—C22 | −150.0 (6) | C31—Sn1—C41—C42 | 75.7 (5) |
C11—Sn1—C21—C22 | −25.0 (6) | C11—Sn1—C41—C42 | −43.7 (5) |
C41—Sn1—C21—C22 | 95.3 (6) | C21—Sn1—C41—C42 | −167.3 (4) |
C26—C21—C22—C23 | 2.1 (10) | C46—C41—C42—C43 | 1.1 (8) |
Sn1—C21—C22—C23 | −177.1 (6) | Sn1—C41—C42—C43 | −177.8 (4) |
C21—C22—C23—C24 | −0.4 (12) | C41—C42—C43—C44 | −0.4 (9) |
C21—C22—C23—Cl3 | 177.4 (6) | C41—C42—C43—Cl8 | −179.2 (4) |
C22—C23—C24—C25 | −1.1 (12) | C42—C43—C44—C45 | −1.2 (9) |
Cl3—C23—C24—C25 | −178.9 (6) | Cl8—C43—C44—C45 | 177.6 (4) |
C23—C24—C25—C26 | 0.9 (11) | C43—C44—C45—C46 | 2.2 (9) |
C23—C24—C25—Cl4 | −177.7 (6) | C43—C44—C45—Cl7 | −177.7 (4) |
C22—C21—C26—C25 | −2.3 (9) | C44—C45—C46—C41 | −1.5 (9) |
Sn1—C21—C26—C25 | 176.9 (4) | Cl7—C45—C46—C41 | 178.4 (4) |
C24—C25—C26—C21 | 0.8 (9) | C42—C41—C46—C45 | −0.2 (8) |
Cl4—C25—C26—C21 | 179.4 (5) | Sn1—C41—C46—C45 | 178.7 (4) |
Experimental details
Crystal data | |
Chemical formula | C24H12Cl8Sn |
Mr | 702.63 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 24.861 (8), 11.908 (3), 18.139 (4) |
β (°) | 100.16 (2) |
V (Å3) | 5286 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 1.79 |
Crystal size (mm) | 0.55 × 0.47 × 0.45 |
Data collection | |
Diffractometer | Rigaku AFC6S diffractometer |
Absorption correction | ψ scan (ABSN in NRCVAX; Gabe et al, 1989) |
Tmin, Tmax | 0.354, 0.449 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19754, 5195, 3632 |
Rint | 0.099 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.050, 0.123, 1.06 |
No. of reflections | 5195 |
No. of parameters | 299 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.70, −0.94 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1985)', MSC/AFC Diffractometer Control Software, DARTD2 in NRCVAX (Gabe et al., 1989), SHELXS97 (Sheldrick, 1997), SHELXL96 (Sheldrick, 1996), ORTEPII (Johnson, 1976) in NRCVAX, NRCVAX and SHELXL96.
Sn1—C31 | 2.134 (6) | Sn1—C41 | 2.135 (6) |
Sn1—C11 | 2.135 (5) | Sn1—C21 | 2.135 (6) |
C31—Sn1—C11 | 111.0 (2) | C26—C21—C22 | 118.2 (6) |
C31—Sn1—C41 | 105.9 (2) | C26—C21—Sn1 | 118.2 (4) |
C11—Sn1—C41 | 108.7 (2) | C22—C21—Sn1 | 123.6 (5) |
C31—Sn1—C21 | 109.6 (2) | C36—C31—C32 | 118.8 (6) |
C11—Sn1—C21 | 113.8 (2) | C36—C31—Sn1 | 120.1 (5) |
C41—Sn1—C21 | 107.5 (2) | C32—C31—Sn1 | 121.1 (4) |
C16—C11—C12 | 118.4 (5) | C46—C41—C42 | 119.3 (5) |
C16—C11—Sn1 | 121.2 (4) | C46—C41—Sn1 | 121.2 (4) |
C12—C11—Sn1 | 120.0 (4) | C42—C41—Sn1 | 119.5 (4) |
C31—Sn1—C11—C16 | 164.0 (5) | C11—Sn1—C31—C36 | 135.8 (5) |
C41—Sn1—C11—C16 | −79.9 (5) | C41—Sn1—C31—C36 | 18.0 (5) |
C21—Sn1—C11—C16 | 39.8 (6) | C21—Sn1—C31—C36 | −97.6 (5) |
C31—Sn1—C11—C12 | −22.7 (6) | C11—Sn1—C31—C32 | −45.4 (5) |
C41—Sn1—C11—C12 | 93.4 (5) | C41—Sn1—C31—C32 | −163.2 (5) |
C21—Sn1—C11—C12 | −146.9 (5) | C21—Sn1—C31—C32 | 81.1 (5) |
Sn1—C11—C12—C13 | −174.2 (5) | Sn1—C31—C32—C33 | −178.1 (4) |
Sn1—C11—C16—C15 | 172.2 (5) | Sn1—C31—C36—C35 | 175.9 (4) |
C31—Sn1—C21—C26 | 30.8 (5) | C31—Sn1—C41—C46 | −103.2 (5) |
C11—Sn1—C21—C26 | 155.8 (4) | C11—Sn1—C41—C46 | 137.4 (4) |
C41—Sn1—C21—C26 | −83.8 (5) | C21—Sn1—C41—C46 | 13.8 (5) |
C31—Sn1—C21—C22 | −150.0 (6) | C31—Sn1—C41—C42 | 75.7 (5) |
C11—Sn1—C21—C22 | −25.0 (6) | C11—Sn1—C41—C42 | −43.7 (5) |
C41—Sn1—C21—C22 | 95.3 (6) | C21—Sn1—C41—C42 | −167.3 (4) |
Sn1—C21—C22—C23 | −177.1 (6) | Sn1—C41—C46—C45 | 178.7 (4) |
Sn1—C21—C26—C25 | 176.9 (4) |
The crystal stuctures of most of the tetraaryltin(IV) compounds reported to date (Lloyd & Brock, 1997; Schürmann et al., 1999; Wharf & Bélanger-Gariépy, 2003) are in close-packed tetragonal space groups, viz. P-421c, I-4 and P-42/n. In these structures, the Ar4Sn molecules are located on sites of −4 symmetry, the molecular conformation with the lowest energy, as determined previously for Ar4Si analogues (Hutchings et al., 1974). This also the case for (C6F5)4Sn (Karipides et al., 1974) and (m-CH3C6H4)4Sn (Karipides & Oertel, 1977), both of which crystallize in I41/a. Deviations from tetragonal symmetry appear to require larger, more obtrusive, ring substituents, examples being [p-CH3S(O2)C6H4]4Sn (Wharf et al., 1990) and (p-CH3CH2C6H4)4Sn (Wharf & Lebuis, 2000), which both crystallize in C2/c with molecules having 2 symmetry, and others with no molecular symmetry, such as (p-CH3CH2OC6H4)4Sn in P21/c (Wharf & Simard, 1991), and both (m-CH3OC6H4)4Sn in C2/c and (o-CH3OC6H4)4Sn in P-1 (Wharf & Simard, 1995).
Desiraju et al. (1986) have proposed that since the Cl atom and the methyl group have almost the same volume, they act as isosteres, with chlorine/methyl analogues being effectively isomorphous. One such example is the toluene and chlorobenzene solvates of 2,3,7,8-tetraphenyl-1,9,10-anthyridine (Madhavi, et al., 1997). However, Ng (1997) found that (p-ClC6H4)4Sn crystallizes in P-1, with no molecular symmetry, and is clearly not isomorphous with (p-CH3C6H4)4Sn in I-4 (Karipides & Wolfe, 1975). We present here the title compound, (I), which has been investigated for comparison with its methyl analogue [3,5-(CH3)2C6H3]4Sn, (II) (Wharf & Bélanger-Gariépy, 2003).
Compound (I) crystallizes in space group C2/c with the molecules having no symmetry and in this way resembles (m-CH3OC6H4)4Sn. However, the Sn—C distances are identical [2.134 (6)–2.135 (6) Å], while the distortion from tetrahedral geometry at the Sn atom is small [105.9 (2)—113.8 (2)°; Fig. 1 and Table 1]. Intermolecular contacts are all greater than the van der Waals distances, the shortest Cl—Cl distance being 3.60 Å and the shortest H—Cl distance being 3.03 Å.
Violations of the chloro–methyl exchange rule are observed when intermolecular directional forces or weak `bonds' are present (Desiraju, 1986). Schürmann et al. (1999) have proposed weak C—H—Cl interactions – still greater than the van der Waals – as a possible rationale for the different packing of (p-ClC6H4)4Sn and (p-CH3C6H4)4Sn. For (I), the packing diagram (Fig. 2) does not show any clear set of such directed interactions, meaning a more detailed comparison of the structures of (I) and (II) is required for the basis of the crystal structure differences to be determined.