Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802007080/tk6061sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802007080/tk6061Isup2.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S1600536802007080/tk6061sup3.pdf |
CCDC reference: 185755
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (C-C) = 0.016 Å
- R factor = 0.060
- wR factor = 0.168
- Data-to-parameter ratio = 27.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSTM_02 Alert C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10 Tmin and Tmax reported: 0.269 0.505 Tmin and Tmax expected: 0.203 0.453 RR = 1.189 Please check that your absorption correction is appropriate. REFLT_03 From the CIF: _diffrn_reflns_theta_max 27.50 From the CIF: _reflns_number_total 5138 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 5464 Completeness (_total/calc) 94.03% Alert C: < 95% complete RINTA_01 Alert C The value of Rint is greater than 0.10 Rint given 0.107 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 27 I1B -SN1B-O1B -C3B 76.00 5.00 1.555 1.555 1.555 1.555 General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.897 Tmax scaled 0.453 Tmin scaled 0.241
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
4 Alert Level C = Please check
Compound (I) was obtained by halide exchange of the corresponding chloride (II). Thus, a solution of (II) (2 mmol) and NaI (ca 20 mmol) in acetone (40 ml) was stirred at room temperature for 1 h. The reaction mixture was then rotary evaporated and the solid residue extracted with chloroform (2 × 30 ml). The combined extracts were rotary evaporated once more and the solid product recrystallized from EtOH to yield crystals of (I) (m.p. 337–339 K) suitable for analysis.
In the final stages, H atoms were introduced in calculated positions with C—H distances of 0.98 and 0.99 Å for methyl and methylene H, respectively, and refined with a riding model with Uiso 1.5 and 1.2Ueq again, respectively. The final difference map showed a number of large peaks as high as, e.g. 3.16 e Å-3 0.87 Å from I3A, but all in the vicinity of Sn or I and attributable to ripples.
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: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 1990).
[SnI3(C4H7O2)] | F(000) = 2048 |
Mr = 586.49 | Dx = 3.277 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3950 (1) Å | Cell parameters from 14043 reflections |
b = 25.8407 (4) Å | θ = 2.9–27.5° |
c = 12.4431 (2) Å | µ = 9.90 mm−1 |
β = 90.4600 (8)° | T = 120 K |
V = 2377.70 (6) Å3 | Block, yellow |
Z = 8 | 0.18 × 0.14 × 0.08 mm |
Enraf-Nonius KappaCCD area-detector diffractometer | 5138 independent reflections |
Radiation source: Enraf-Nonius FR591 rotating anode | 4645 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.107 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ϕ and ω scans to fill the Ewald sphere | h = −9→9 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | k = −33→33 |
Tmin = 0.269, Tmax = 0.505 | l = −16→16 |
20814 measured reflections |
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)] = 0.060 | H-atom parameters constrained |
wR(F2) = 0.168 | w = 1/[σ2(Fo2) + (0.0892P)2 + 21.9385P] where P = (Fo2 + 2Fc2)/3 |
S = 1.14 | (Δ/σ)max = 0.001 |
5138 reflections | Δρmax = 3.16 e Å−3 |
184 parameters | Δρmin = −2.71 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: 0.00204 (18) |
[SnI3(C4H7O2)] | V = 2377.70 (6) Å3 |
Mr = 586.49 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 7.3950 (1) Å | µ = 9.90 mm−1 |
b = 25.8407 (4) Å | T = 120 K |
c = 12.4431 (2) Å | 0.18 × 0.14 × 0.08 mm |
β = 90.4600 (8)° |
Enraf-Nonius KappaCCD area-detector diffractometer | 5138 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995, 1997) | 4645 reflections with I > 2σ(I) |
Tmin = 0.269, Tmax = 0.505 | Rint = 0.107 |
20814 measured reflections |
R[F2 > 2σ(F2)] = 0.060 | 0 restraints |
wR(F2) = 0.168 | H-atom parameters constrained |
S = 1.14 | w = 1/[σ2(Fo2) + (0.0892P)2 + 21.9385P] where P = (Fo2 + 2Fc2)/3 |
5138 reflections | Δρmax = 3.16 e Å−3 |
184 parameters | Δρmin = −2.71 e Å−3 |
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) 0.3242(0.0297) x + 18.3176(0.0831) y - 8.7638(0.0414) z = 3.7257(0.0949) * -0.0151 (0.0046) Sn1A * 0.0081 (0.0081) C1A * 0.0117 (0.0096) C2A * -0.0385 (0.0082) C3A * 0.0338 (0.0059) O1A -0.0300 (0.0131) I1A -2.3806 (0.0087) I2A 2.1109 (0.0104) I3A -0.1512 (0.0146) O2A -0.1757 (0.0213) C4A Rms deviation of fitted atoms = 0.0247 1.0427(0.0309) x + 13.7880(0.0973) y + 10.3621(0.0347) z = 11.3573(0.0163) Angle to previous plane (with approximate e.s.d.) = 78.31 (0.28) * 0.1758 (0.0047) Sn1B * -0.3236 (0.0079) C1B * 0.2835 (0.0084) C2B * -0.0064 (0.0080) C3B * -0.1294 (0.0061) O1B 0.3987 (0.0131) I1B 2.7021 (0.0066) I2B -1.5704 (0.0127) I3B -0.1057 (0.0147) O2B -0.4687 (0.0204) C4B Rms deviation of fitted atoms = 0.2158 |
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. Anisotropic displacement parameters refined for all non-H atoms. H atoms in calculated positions and refined with a riding model. Intensity data 93.6% complete out to 50 °. 2-theta. Max Delta(rho) 3.16 e-Ang**-3 0.87 from I3A and largest of ca 24 large features (down to 1.57 e-Ang**-3 approx. 1 A ng distant from Sn or I) and attributed to ripple. |
x | y | z | Uiso*/Ueq | ||
Sn1A | 0.33608 (9) | 0.63670 (2) | 0.91984 (5) | 0.0201 (2) | |
I1A | 0.13667 (11) | 0.70147 (3) | 1.04953 (6) | 0.0354 (2) | |
I2A | 0.21626 (10) | 0.54496 (2) | 0.99356 (7) | 0.0321 (2) | |
I3A | 0.19303 (10) | 0.66415 (3) | 0.72933 (6) | 0.0300 (2) | |
C1A | 0.6052 (14) | 0.6572 (4) | 0.9700 (9) | 0.027 (2) | |
H1A1 | 0.6236 | 0.6946 | 0.9572 | 0.032* | |
H1A2 | 0.6174 | 0.6510 | 1.0482 | 0.032* | |
C2A | 0.7492 (16) | 0.6277 (6) | 0.9133 (11) | 0.041 (3) | |
H2A1 | 0.8272 | 0.6528 | 0.8754 | 0.049* | |
H2A2 | 0.8253 | 0.6102 | 0.9681 | 0.049* | |
C3A | 0.6881 (14) | 0.5881 (4) | 0.8339 (9) | 0.026 (2) | |
O1A | 0.5295 (10) | 0.5820 (3) | 0.8070 (7) | 0.0305 (17) | |
O2A | 0.8200 (12) | 0.5605 (3) | 0.7940 (7) | 0.038 (2) | |
C4A | 0.7682 (19) | 0.5219 (5) | 0.7141 (11) | 0.042 (3) | |
H4A1 | 0.6549 | 0.5053 | 0.7356 | 0.064* | |
H4A2 | 0.8635 | 0.4957 | 0.7089 | 0.064* | |
H4A3 | 0.7514 | 0.5387 | 0.6441 | 0.064* | |
Sn1B | 0.14771 (10) | 0.34482 (2) | 0.63933 (6) | 0.0235 (2) | |
I1B | 0.33283 (13) | 0.26872 (3) | 0.74346 (7) | 0.0382 (2) | |
I2B | 0.23598 (11) | 0.42592 (2) | 0.76633 (6) | 0.0288 (2) | |
I3B | 0.32701 (12) | 0.34466 (3) | 0.45298 (6) | 0.0374 (2) | |
C1B | −0.1341 (17) | 0.3264 (4) | 0.6440 (10) | 0.033 (3) | |
H1B1 | −0.1676 | 0.3065 | 0.5788 | 0.040* | |
H1B2 | −0.1581 | 0.3043 | 0.7074 | 0.040* | |
C2B | −0.2493 (15) | 0.3747 (4) | 0.6500 (11) | 0.034 (3) | |
H2B1 | −0.3781 | 0.3654 | 0.6391 | 0.040* | |
H2B2 | −0.2362 | 0.3906 | 0.7220 | 0.040* | |
C3B | −0.1932 (16) | 0.4125 (4) | 0.5660 (9) | 0.029 (2) | |
O1B | −0.0368 (10) | 0.4159 (3) | 0.5339 (6) | 0.0268 (16) | |
O2B | −0.3236 (11) | 0.4425 (3) | 0.5296 (7) | 0.0351 (19) | |
C4B | −0.2761 (17) | 0.4781 (5) | 0.4425 (11) | 0.035 (3) | |
H4B1 | −0.1802 | 0.5015 | 0.4671 | 0.053* | |
H4B2 | −0.3829 | 0.4983 | 0.4215 | 0.053* | |
H4B3 | −0.2335 | 0.4582 | 0.3806 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1A | 0.0209 (4) | 0.0185 (3) | 0.0209 (4) | −0.0019 (2) | −0.0055 (3) | −0.0008 (2) |
I1A | 0.0444 (5) | 0.0292 (4) | 0.0326 (5) | 0.0032 (3) | 0.0004 (3) | −0.0091 (3) |
I2A | 0.0331 (4) | 0.0207 (3) | 0.0427 (5) | −0.0037 (3) | −0.0012 (3) | 0.0059 (3) |
I3A | 0.0313 (4) | 0.0347 (4) | 0.0238 (4) | 0.0063 (3) | −0.0080 (3) | 0.0022 (3) |
C1A | 0.018 (5) | 0.035 (5) | 0.027 (6) | −0.010 (4) | −0.005 (4) | −0.007 (4) |
C2A | 0.015 (6) | 0.067 (8) | 0.041 (7) | 0.009 (5) | 0.000 (5) | −0.018 (6) |
C3A | 0.016 (5) | 0.028 (5) | 0.035 (6) | 0.003 (4) | −0.006 (4) | 0.000 (4) |
O1A | 0.021 (4) | 0.034 (4) | 0.037 (5) | 0.006 (3) | −0.006 (3) | −0.008 (3) |
O2A | 0.039 (5) | 0.042 (4) | 0.032 (5) | 0.014 (4) | −0.001 (4) | 0.004 (4) |
C4A | 0.043 (8) | 0.044 (7) | 0.040 (7) | 0.013 (6) | −0.003 (6) | −0.008 (6) |
Sn1B | 0.0303 (4) | 0.0184 (3) | 0.0218 (4) | 0.0037 (3) | −0.0058 (3) | −0.0001 (2) |
I1B | 0.0562 (6) | 0.0242 (4) | 0.0341 (5) | 0.0138 (3) | −0.0127 (4) | 0.0007 (3) |
I2B | 0.0404 (5) | 0.0204 (3) | 0.0254 (4) | 0.0021 (3) | −0.0075 (3) | −0.0016 (2) |
I3B | 0.0484 (5) | 0.0399 (4) | 0.0240 (4) | 0.0103 (3) | −0.0003 (3) | −0.0033 (3) |
C1B | 0.043 (7) | 0.021 (5) | 0.036 (7) | −0.011 (4) | −0.006 (5) | −0.001 (4) |
C2B | 0.015 (5) | 0.036 (6) | 0.050 (8) | −0.008 (4) | −0.011 (5) | 0.015 (5) |
C3B | 0.031 (6) | 0.021 (4) | 0.034 (6) | 0.003 (4) | −0.006 (5) | 0.005 (4) |
O1B | 0.022 (4) | 0.028 (3) | 0.031 (4) | −0.001 (3) | 0.004 (3) | 0.001 (3) |
O2B | 0.024 (4) | 0.035 (4) | 0.046 (5) | 0.004 (3) | −0.001 (4) | 0.017 (4) |
C4B | 0.032 (7) | 0.034 (6) | 0.041 (7) | 0.001 (5) | −0.003 (5) | 0.015 (5) |
Sn1A—C1A | 2.147 (10) | Sn1B—C1B | 2.139 (12) |
Sn1A—O1A | 2.459 (8) | Sn1B—O1B | 2.631 (8) |
Sn1A—I3A | 2.6835 (9) | Sn1B—I3B | 2.6803 (11) |
Sn1A—I2A | 2.6944 (9) | Sn1B—I2B | 2.7016 (9) |
Sn1A—I1A | 2.7601 (10) | Sn1B—I1B | 2.7188 (9) |
C1A—C2A | 1.492 (16) | C1B—C2B | 1.513 (16) |
C1A—H1A1 | 0.9900 | C1B—H1B1 | 0.9900 |
C1A—H1A2 | 0.9900 | C1B—H1B2 | 0.9900 |
C2A—C3A | 1.491 (16) | C2B—C3B | 1.493 (16) |
C2A—H2A1 | 0.9900 | C2B—H2B1 | 0.9900 |
C2A—H2A2 | 0.9900 | C2B—H2B2 | 0.9900 |
C3A—O1A | 1.227 (13) | C3B—O1B | 1.229 (14) |
C3A—O2A | 1.308 (14) | C3B—O2B | 1.316 (13) |
O2A—C4A | 1.458 (16) | O2B—C4B | 1.465 (14) |
C4A—H4A1 | 0.9800 | C4B—H4B1 | 0.9800 |
C4A—H4A2 | 0.9800 | C4B—H4B2 | 0.9800 |
C4A—H4A3 | 0.9800 | C4B—H4B3 | 0.9800 |
C1A—Sn1A—O1A | 76.5 (3) | C1B—Sn1B—O1B | 70.6 (3) |
C1A—Sn1A—I3A | 123.3 (3) | C1B—Sn1B—I3B | 120.8 (3) |
O1A—Sn1A—I3A | 82.80 (19) | O1B—Sn1B—I3B | 80.09 (17) |
C1A—Sn1A—I2A | 115.1 (3) | C1B—Sn1B—I2B | 112.8 (3) |
O1A—Sn1A—I2A | 83.3 (2) | O1B—Sn1B—I2B | 82.66 (17) |
I3A—Sn1A—I2A | 113.89 (3) | I3B—Sn1B—I2B | 112.85 (4) |
C1A—Sn1A—I1A | 100.3 (3) | C1B—Sn1B—I1B | 108.2 (3) |
O1A—Sn1A—I1A | 176.67 (19) | O1B—Sn1B—I1B | 177.89 (17) |
I3A—Sn1A—I1A | 98.48 (3) | I3B—Sn1B—I1B | 99.24 (4) |
I2A—Sn1A—I1A | 98.96 (3) | I2B—Sn1B—I1B | 99.43 (3) |
C2A—C1A—Sn1A | 113.6 (7) | C2B—C1B—Sn1B | 111.5 (7) |
C2A—C1A—H1A1 | 108.8 | C2B—C1B—H1B1 | 109.3 |
Sn1A—C1A—H1A1 | 108.8 | Sn1B—C1B—H1B1 | 109.3 |
C2A—C1A—H1A2 | 108.8 | C2B—C1B—H1B2 | 109.3 |
Sn1A—C1A—H1A2 | 108.8 | Sn1B—C1B—H1B2 | 109.3 |
H1A1—C1A—H1A2 | 107.7 | H1B1—C1B—H1B2 | 108.0 |
C3A—C2A—C1A | 116.8 (10) | C3B—C2B—C1B | 110.2 (10) |
C3A—C2A—H2A1 | 108.1 | C3B—C2B—H2B1 | 109.6 |
C1A—C2A—H2A1 | 108.1 | C1B—C2B—H2B1 | 109.6 |
C3A—C2A—H2A2 | 108.1 | C3B—C2B—H2B2 | 109.6 |
C1A—C2A—H2A2 | 108.1 | C1B—C2B—H2B2 | 109.6 |
H2A1—C2A—H2A2 | 107.3 | H2B1—C2B—H2B2 | 108.1 |
O1A—C3A—O2A | 122.8 (10) | O1B—C3B—O2B | 122.3 (10) |
O1A—C3A—C2A | 123.5 (10) | O1B—C3B—C2B | 122.8 (10) |
O2A—C3A—C2A | 113.7 (9) | O2B—C3B—C2B | 114.9 (10) |
C3A—O1A—Sn1A | 109.3 (7) | C3B—O1B—Sn1B | 105.9 (6) |
C3A—O2A—C4A | 116.0 (10) | C3B—O2B—C4B | 116.4 (9) |
O2A—C4A—H4A1 | 109.5 | O2B—C4B—H4B1 | 109.5 |
O2A—C4A—H4A2 | 109.5 | O2B—C4B—H4B2 | 109.5 |
H4A1—C4A—H4A2 | 109.5 | H4B1—C4B—H4B2 | 109.5 |
O2A—C4A—H4A3 | 109.5 | O2B—C4B—H4B3 | 109.5 |
H4A1—C4A—H4A3 | 109.5 | H4B1—C4B—H4B3 | 109.5 |
H4A2—C4A—H4A3 | 109.5 | H4B2—C4B—H4B3 | 109.5 |
O1A—Sn1A—C1A—C2A | −1.1 (9) | I3B—Sn1B—C1B—C2B | −100.0 (8) |
I3A—Sn1A—C1A—C2A | −72.9 (10) | I2B—Sn1B—C1B—C2B | 37.9 (9) |
I2A—Sn1A—C1A—C2A | 74.6 (10) | I1B—Sn1B—C1B—C2B | 146.9 (8) |
I1A—Sn1A—C1A—C2A | 179.7 (9) | Sn1B—C1B—C2B—C3B | 49.3 (11) |
Sn1A—C1A—C2A—C3A | −1.6 (16) | C1B—C2B—C3B—O1B | −30.9 (16) |
C1A—C2A—C3A—O1A | 6 (2) | C1B—C2B—C3B—O2B | 149.8 (10) |
C1A—C2A—C3A—O2A | −174.3 (11) | O2B—C3B—O1B—Sn1B | −179.8 (9) |
O2A—C3A—O1A—Sn1A | 173.9 (9) | C2B—C3B—O1B—Sn1B | 1.0 (13) |
C2A—C3A—O1A—Sn1A | −7.0 (14) | C1B—Sn1B—O1B—C3B | 19.9 (8) |
C1A—Sn1A—O1A—C3A | 4.3 (8) | I3B—Sn1B—O1B—C3B | 147.7 (7) |
I3A—Sn1A—O1A—C3A | 131.2 (7) | I2B—Sn1B—O1B—C3B | −97.4 (7) |
I2A—Sn1A—O1A—C3A | −113.6 (7) | I1B—Sn1B—O1B—C3B | 76 (5) |
O1A—C3A—O2A—C4A | 0.5 (16) | O1B—C3B—O2B—C4B | 4.3 (17) |
C2A—C3A—O2A—C4A | −178.7 (11) | C2B—C3B—O2B—C4B | −176.5 (10) |
O1B—Sn1B—C1B—C2B | −35.0 (8) |
Experimental details
Crystal data | |
Chemical formula | [SnI3(C4H7O2)] |
Mr | 586.49 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 120 |
a, b, c (Å) | 7.3950 (1), 25.8407 (4), 12.4431 (2) |
β (°) | 90.4600 (8) |
V (Å3) | 2377.70 (6) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 9.90 |
Crystal size (mm) | 0.18 × 0.14 × 0.08 |
Data collection | |
Diffractometer | Enraf-Nonius KappaCCD area-detector diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995, 1997) |
Tmin, Tmax | 0.269, 0.505 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20814, 5138, 4645 |
Rint | 0.107 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.060, 0.168, 1.14 |
No. of reflections | 5138 |
No. of parameters | 184 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0892P)2 + 21.9385P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 3.16, −2.71 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), SHELXL97 and PLATON (Spek, 1990).
Mol. A | Mol. B | |
Sn1—I1 | 2.7601 (10) | 2.7188 (9) |
Sn1—I2 | 2.6944 (9) | 2.7016 (9) |
Sn1—I3 | 2.6835 (9) | 2.6803 (11) |
Sn1—O1 | 2.459 (8) | 2.631 (8) |
Sn1—C1 | 2.147 (10) | 2.139 (12) |
I2—Sn1—I3 | 113.89 (3) | 112.85 (4) |
I2—Sn1—C1 | 115.1 (3) | 112.8 (3) |
I3—Sn1—C1 | 123.3 (3) | 120.8 (3) |
I1—Sn1—I2 | 98.96 (3) | 99.43 (3) |
I1—Sn1—I3 | 98.48 (3) | 99.24 (4) |
I1—Sn1—C1 | 100.3 (3) | 108.2 (3) |
O1—Sn1—I2 | 83.3 (2) | 82.66 (17) |
O1—Sn1—I3 | 82.80 (19) | 80.09 (17) |
O1—Sn1—C1 | 76.5 (3) | 70.6 (3) |
O1—Sn1—I1 | 176.67 (19) | 177.89 (17) |
I-A | I-B | IIa | IIIb | |
O1—Sn1—C1 | 76.5 (3) | 70.6 (3) | 77.2 | 78.0 (3) |
Sn1—C1—C2 | 113.6 (7) | 111.5 (7) | 113.4 | 112.8 (6) |
C1—C2—C3 | 116.8 (10) | 110.2 (10) | 114.1 | 114.5 (7) |
C2—C3—O1 | 123.5 (10) | 122.8 (10) | 124.3 | 123.2 (7) |
C3—O1—Sn1 | 109.3 (7) | 105.9 (6) | 110.1 | 111.4 (4) |
O1—Sn1—C1—C2 | -1.1 (9) | -35.0 (8) | -6.9 | 1.7 (5) |
Sn1—C1—C2—C3 | -1.6 (16) | 49.3 (11) | 10.3 | -4.1 (8) |
C1—C2—C3—O1 | 6(2) | -30.9 (16) | -8.9 | 5.9 (10) |
C2—C3—O1—Sn1 | -7.0 (14) | 1.0 (13) | 2.6 | -4.3 (8) |
C3—O1—Sn1—C1 | 4.3 (8) | 19.9 (8) | 2.6 | 1.3 (5) |
Notes: (a) CMESNC (Harrison et al. 1979), no s.u.'s available in CSD entry; (b) FAYSUT (Howie et al. 1986). |
D—H···A | D—H | H···A | D···A | D—H···A |
C1B—H1B2···I1Ai | 0.99 | 3.03 | 3.881 (13) | 145 |
C1B—H1B1···I1Aii | 0.99 | 3.16 | 4.027 (11) | 147 |
Symmetry codes (i) -x,1-y,2-z; (ii) -x,y-1/2,3/2-z. |
At this time, the Cambridge Structural Database (CSD; Allen & Kennard, 1993) contains entries for approximately 30 estertin compounds. Two of these, namely (2-carbomethoxyethyl)trichlorotin (CMESNC; Harrison et al., 1979), (II), and (2-carboisopropoxyethyl)trichlorotin (FAYSUT; Howie et al., 1986), (III), are particularly relevant to the discussion of the title compound, (I).
Unlike (II) and (III), in (I), the asymmetric unit contains not one but two molecules. Both molecules in (I) are labelled in an identical manner largely compatible with that used for the molecules of (II) and (III) (Fig. 1), but distinguished by suffix A or B. Bond distances and angles in molecules A and B of (I) involving Sn are given in Table 1. Here it is clear, as exemplified in Fig. 1, that Sn is five-coordinate in the form of a distorted trigonal bipyramid with axial O1 and I1 and equatorial I2, I3 and C1 in both molecules. Particularly significant are the longer Sn1—I1 and shorter Sn1—O1 trans-axial bonds in molecule A compared with bonds of the same type in molecule B. Aside from the inevitable differences between Sn—I, Sn—C and Sn—O distances the most obvious distortion of the coordination of Sn lies in the O1—Sn1—C1 chelate bite angle but this distortion, while still very obvious, is less for molecule A than it is for molecule B. Indeed, obviously excepting the trans-axial angle O1—Sn1—I1, almost all of the angles at Sn are closer to the ideal values of 120 or 90° in molecule A than they are in molecule B.
Table 2 compares the bond and torsion angles within the five-membered chelate rings of molecules A and B of (I) and the molecules of (II) and (III). While there is comparatively little variation in the bond angles the torsion angles clearly demonstrate significant puckering in the chelate ring of molecule B of (I) [pucker parameters (Cremer & Pople, 1975) Q2 = 0.498 (10) Å and ϕ2 = 150.8 (13)°], much less in the molecule of (II) [Q2 0.097 Å and ϕ2 = 138.5°] and closest description envelope with C1 at the point of the flap in both of these and virtually none in molecule A of (I) and the molecule of (III) [Q2 and ϕ2 found indeterminate by PLATON for these last two]. The r.m.s. deviations for the fitted atoms for each of the Sn1/C1/C2/C3/O1 planes [0.216, 0.043, 0.025 and 0.018 Å for molecule B of (I), (II), molecule A of (I) and for (III), respectively] confirm the decrease in puckering or increase in planarity in the order given.
Another major difference between molecules A and B of (I) is that I1A of molecule A acts as acceptor for the two C—H···I weak intermolecular hydrogen bonds given in Table 3. There is no corresponding interaction in the case of molecule B. These contacts interconnect the molecules of both types to form zigzag chains propagated in the direction of c as shown in Fig. 2. As indicated in Fig. 3, the chains lie face-to-face and related one to the next by cell translation in the direction of a, forming layers centred on the c-glides of the space group P21/c at y = 1/4 and 3/4. Adjacent layers are related by crystallographic centres of symmetry.
It is suggested, therefore, that the comparatively short, relative to molecule B, Sn1A–O1A distance and the concomitant relative planarity of the chelate ring in molecule A is probably due to lengthening and weakening of the Sn1A—I1A bond due to the role of I1A as hydrogen bond, weak though the bonds are, acceptor.