Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270102010375/sk1559sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102010375/sk1559Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270102010375/sk1559IIsup3.hkl |
CCDC references: 192953; 192954
Compound (I) was prepared from Ph3SnCH2I, HSC6H4NO2 and NaOEt (2 mmol scale) in EtOH (20 ml). After refluxing for 2 h, the mixture was cooled, all volatiles removed and the residue recrystallized from EtOH (m.p. 416–418 K). Analysis found: C 58.4, H 5.5, S 6.3, N 3.1%; calculated for C24H21NO2SSn: C 58.0, H 4.1, S 6.2, N 2.7%. Spectroscopic analysis: 1H NMR (250 Hz, CDCl3, δ, p.p.m.): 2.88 [s, 2H, J(119,117Sn-1H) = 48.8 Hz, CH2], 7.41 (m, 11H, m-H + p-H of Ph3Sn + 2H from C6H4), 7.60 [m, 6H, J(119,117Sn-1H) ~57 Hz, o-H of Ph3Sn], 8.10 (d, 2H, J = 8.8 Hz, C6H4); 13C NMR (63.3 Hz, CDCl3, δ, p.p.m.): 5.2 (CH2), 123.8 (C3), 124.6 (C2), 128.9 (m-C of Ph3Sn), 129.7 (p-C of Ph3Sn), 136.7 (i-C of Ph3Sn), 137.0 (o-C of Ph3Sn), 144.0 (C1), 152.7 (C4); 119Sn NMR (93.3 Hz, CD2Cl2, δ, p.p.m.): -118; IR (KBr, cm-1): 1578 and 1339 (NO2); Raman (cm-1): 1587, 1331.
Compound (II) was obtained by H2O2 oxidation (30% solution in water) of (I) in a mixed H2O—CH2Cl2 medium. After stirring the reaction mixture overnight at room temperature, all volatiles were removed and the residue was recrystallized from EtOH (m.p. 472–475 K). Spectroscopic analysis: 1H NMR (250 Hz, CDCl3, δ, p.p.m.): 3.44 [s, 2H, J(119,117Sn-1H) = 41.2 Hz, CH2], 7.43 (m, 9H, p-H + m-H of Ph3Sn), 7.63 [m, 6H, J(119,117Sn-1H) ~60 Hz, o-H of Ph3Sn], 8.06 (d, 2H, J = 8.6 Hz, C6H4), 8.28 (m, 2H, J = 8.6 Hz, C6H4); 13C NMR (63.3 Hz, CDCl3, δ, p.p.m.): 44.5 (CH2), 124.4 (C3), 128.2 (C2), 129.0 (m-C of Ph3Sn), 129.9 (p-C of Ph3Sn), 135.8 (i-C of Ph3Sn), 137.0 (o-C of Ph3Sn), C4 and C1 not observed; IR (nujol mull, cm-1): 1527 and 1304 (NO2), 1377 and 1145 (SO2).
Structure (I) was solved using Patterson methods (SHELXS86; Sheldrick, 1990) in P1, and then the coordinates were converted to P1. A l l H atoms were placed in geometrical positions, with C—H distances of 0.95–0.99 Å, and refined using a riding model. Are these the correct constraints?
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998) for (I); SMART (Bruker, 1999) for (II). Cell refinement: DENZO and COLLECT for (I); SAINT (Bruker, 1999) for (II). Data reduction: DENZO and COLLECT for (I); SAINT for (II). Program(s) used to solve structure: SHELXS86 (Sheldrick, 1990) for (I); SHELXS97 (Sheldrick, 1990) for (II). For both compounds, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX in OSCAIL (McArdle, 1994, 2000) and ORTEPIII for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
[Sn(C6H5)3(C7H6NO2S)] | Z = 2 |
Mr = 518.18 | F(000) = 520 |
Triclinic, P1 | Dx = 1.555 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.6442 (1) Å | Cell parameters from 12524 reflections |
b = 10.3070 (2) Å | θ = 2.9–27.5° |
c = 17.2597 (4) Å | µ = 1.27 mm−1 |
α = 100.3385 (8)° | T = 150 K |
β = 98.6403 (9)° | Needle, yellow |
γ = 103.6969 (16)° | 0.40 × 0.10 × 0.03 mm |
V = 1106.51 (4) Å3 |
Nonius KappaCCD area-detector diffractometer | 5030 independent reflections |
Radiation source: fine-focus sealed tube | 4460 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.052 |
ϕ/ω scans | θmax = 27.5°, θmin = 3.2° |
Absorption correction: empirical (using intensity measurements) (SORTAV; Blessing, 1995, 1997) | h = −8→8 |
Tmin = 0.817, Tmax = 0.992 | k = −13→13 |
16551 measured reflections | l = −22→22 |
Refinement on F2 | Primary atom site location: heavy-atom method |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0434P)2] where P = (Fo2 + 2Fc2)/3 |
5030 reflections | (Δ/σ)max = 0.001 |
271 parameters | Δρmax = 0.82 e Å−3 |
0 restraints | Δρmin = −1.39 e Å−3 |
[Sn(C6H5)3(C7H6NO2S)] | γ = 103.6969 (16)° |
Mr = 518.18 | V = 1106.51 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.6442 (1) Å | Mo Kα radiation |
b = 10.3070 (2) Å | µ = 1.27 mm−1 |
c = 17.2597 (4) Å | T = 150 K |
α = 100.3385 (8)° | 0.40 × 0.10 × 0.03 mm |
β = 98.6403 (9)° |
Nonius KappaCCD area-detector diffractometer | 5030 independent reflections |
Absorption correction: empirical (using intensity measurements) (SORTAV; Blessing, 1995, 1997) | 4460 reflections with I > 2σ(I) |
Tmin = 0.817, Tmax = 0.992 | Rint = 0.052 |
16551 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.079 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.82 e Å−3 |
5030 reflections | Δρmin = −1.39 e Å−3 |
271 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. 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. |
x | y | z | Uiso*/Ueq | ||
Sn1 | 0.53277 (2) | 0.721867 (15) | 0.286014 (9) | 0.02319 (7) | |
N1 | 1.4532 (3) | 0.7214 (2) | −0.03471 (13) | 0.0299 (5) | |
O1 | 1.5414 (3) | 0.81168 (19) | −0.06564 (12) | 0.0400 (5) | |
O2 | 1.4945 (4) | 0.6110 (2) | −0.03954 (14) | 0.0493 (6) | |
C1 | 0.9971 (4) | 0.7958 (2) | 0.10086 (14) | 0.0235 (5) | |
C2 | 1.0489 (4) | 0.6710 (2) | 0.09232 (15) | 0.0250 (5) | |
H2 | 0.9807 | 0.6022 | 0.1169 | 0.030* | |
C3 | 1.1991 (4) | 0.6474 (2) | 0.04825 (14) | 0.0250 (5) | |
H3 | 1.2368 | 0.5634 | 0.0433 | 0.030* | |
C4 | 1.2935 (4) | 0.7470 (2) | 0.01147 (14) | 0.0239 (5) | |
C5 | 1.2417 (4) | 0.8704 (3) | 0.01735 (15) | 0.0272 (5) | |
H5 | 1.3066 | 0.9372 | −0.0092 | 0.033* | |
C6 | 1.0955 (4) | 0.8945 (2) | 0.06216 (15) | 0.0281 (5) | |
H6 | 1.0601 | 0.9793 | 0.0671 | 0.034* | |
S1 | 0.82112 (11) | 0.84236 (7) | 0.15992 (4) | 0.03428 (16) | |
C7 | 0.7117 (4) | 0.6909 (3) | 0.19205 (16) | 0.0307 (6) | |
H1A | 0.8280 | 0.6528 | 0.2119 | 0.037* | |
H1B | 0.6178 | 0.6221 | 0.1451 | 0.037* | |
C11 | 0.4586 (3) | 0.9146 (2) | 0.30288 (14) | 0.0228 (5) | |
C12 | 0.4451 (4) | 0.9868 (3) | 0.24234 (15) | 0.0286 (5) | |
H12 | 0.4713 | 0.9508 | 0.1913 | 0.034* | |
C13 | 0.3939 (4) | 1.1108 (3) | 0.25563 (16) | 0.0331 (6) | |
H13 | 0.3839 | 1.1586 | 0.2136 | 0.040* | |
C14 | 0.3575 (4) | 1.1648 (3) | 0.32964 (17) | 0.0334 (6) | |
H14 | 0.3226 | 1.2497 | 0.3386 | 0.040* | |
C15 | 0.3720 (4) | 1.0956 (3) | 0.39042 (16) | 0.0349 (6) | |
H15 | 0.3477 | 1.1329 | 0.4415 | 0.042* | |
C16 | 0.4220 (4) | 0.9711 (3) | 0.37726 (15) | 0.0299 (6) | |
H16 | 0.4314 | 0.9238 | 0.4196 | 0.036* | |
C21 | 0.7299 (4) | 0.7186 (2) | 0.39528 (14) | 0.0245 (5) | |
C22 | 0.9143 (4) | 0.8229 (3) | 0.42788 (16) | 0.0315 (6) | |
H22 | 0.9483 | 0.8974 | 0.4024 | 0.038* | |
C23 | 1.0497 (4) | 0.8210 (3) | 0.49659 (17) | 0.0384 (7) | |
H23 | 1.1751 | 0.8935 | 0.5179 | 0.046* | |
C24 | 1.0018 (5) | 0.7129 (3) | 0.53421 (16) | 0.0407 (7) | |
H24 | 1.0948 | 0.7111 | 0.5813 | 0.049* | |
C25 | 0.8199 (5) | 0.6083 (3) | 0.50353 (17) | 0.0392 (7) | |
H25 | 0.7870 | 0.5345 | 0.5296 | 0.047* | |
C26 | 0.6843 (4) | 0.6102 (3) | 0.43459 (16) | 0.0326 (6) | |
H26 | 0.5591 | 0.5373 | 0.4137 | 0.039* | |
C31 | 0.2639 (4) | 0.5467 (2) | 0.25865 (14) | 0.0230 (5) | |
C32 | 0.0969 (4) | 0.5401 (3) | 0.29973 (15) | 0.0283 (5) | |
H32 | 0.1020 | 0.6149 | 0.3419 | 0.034* | |
C33 | −0.0751 (4) | 0.4263 (3) | 0.27971 (17) | 0.0354 (6) | |
H33 | −0.1880 | 0.4238 | 0.3078 | 0.042* | |
C34 | −0.0848 (4) | 0.3153 (3) | 0.21886 (17) | 0.0364 (6) | |
H34 | −0.2034 | 0.2370 | 0.2053 | 0.044* | |
C35 | 0.0798 (4) | 0.3200 (3) | 0.17842 (16) | 0.0337 (6) | |
H35 | 0.0746 | 0.2445 | 0.1368 | 0.040* | |
C36 | 0.2524 (4) | 0.4341 (2) | 0.19803 (15) | 0.0269 (5) | |
H36 | 0.3648 | 0.4358 | 0.1698 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Sn1 | 0.02658 (11) | 0.02348 (11) | 0.02110 (11) | 0.00822 (7) | 0.00777 (7) | 0.00462 (7) |
N1 | 0.0367 (12) | 0.0279 (12) | 0.0257 (11) | 0.0074 (9) | 0.0131 (9) | 0.0037 (9) |
O1 | 0.0494 (12) | 0.0351 (11) | 0.0420 (12) | 0.0088 (9) | 0.0288 (9) | 0.0124 (9) |
O2 | 0.0690 (15) | 0.0367 (12) | 0.0617 (15) | 0.0283 (11) | 0.0435 (12) | 0.0170 (11) |
C1 | 0.0213 (11) | 0.0256 (13) | 0.0242 (12) | 0.0066 (9) | 0.0064 (9) | 0.0050 (10) |
C2 | 0.0276 (12) | 0.0237 (13) | 0.0265 (13) | 0.0074 (10) | 0.0094 (10) | 0.0083 (10) |
C3 | 0.0289 (12) | 0.0223 (12) | 0.0234 (13) | 0.0073 (10) | 0.0059 (10) | 0.0033 (10) |
C4 | 0.0229 (11) | 0.0255 (13) | 0.0222 (12) | 0.0055 (10) | 0.0072 (9) | 0.0017 (10) |
C5 | 0.0323 (13) | 0.0247 (13) | 0.0251 (13) | 0.0050 (10) | 0.0095 (10) | 0.0078 (10) |
C6 | 0.0317 (13) | 0.0228 (13) | 0.0332 (14) | 0.0100 (10) | 0.0106 (11) | 0.0080 (11) |
S1 | 0.0373 (4) | 0.0279 (3) | 0.0474 (4) | 0.0140 (3) | 0.0249 (3) | 0.0128 (3) |
C7 | 0.0385 (14) | 0.0288 (14) | 0.0305 (14) | 0.0124 (11) | 0.0163 (11) | 0.0087 (11) |
C11 | 0.0212 (11) | 0.0241 (12) | 0.0216 (12) | 0.0051 (9) | 0.0054 (9) | 0.0023 (10) |
C12 | 0.0335 (13) | 0.0336 (14) | 0.0235 (13) | 0.0153 (11) | 0.0093 (10) | 0.0071 (11) |
C13 | 0.0346 (14) | 0.0369 (15) | 0.0369 (15) | 0.0169 (12) | 0.0133 (12) | 0.0165 (12) |
C14 | 0.0375 (15) | 0.0266 (14) | 0.0400 (16) | 0.0144 (11) | 0.0119 (12) | 0.0065 (12) |
C15 | 0.0426 (16) | 0.0369 (15) | 0.0271 (14) | 0.0179 (12) | 0.0101 (12) | −0.0004 (12) |
C16 | 0.0354 (14) | 0.0319 (14) | 0.0242 (13) | 0.0116 (11) | 0.0074 (11) | 0.0067 (11) |
C21 | 0.0279 (12) | 0.0270 (13) | 0.0207 (12) | 0.0116 (10) | 0.0079 (10) | 0.0028 (10) |
C22 | 0.0360 (14) | 0.0285 (14) | 0.0306 (14) | 0.0089 (11) | 0.0083 (11) | 0.0066 (11) |
C23 | 0.0323 (14) | 0.0437 (17) | 0.0328 (15) | 0.0085 (12) | 0.0003 (12) | 0.0001 (13) |
C24 | 0.0444 (16) | 0.0574 (19) | 0.0265 (15) | 0.0272 (15) | 0.0043 (12) | 0.0093 (14) |
C25 | 0.0523 (18) | 0.0466 (17) | 0.0344 (16) | 0.0290 (14) | 0.0154 (13) | 0.0228 (14) |
C26 | 0.0366 (14) | 0.0309 (14) | 0.0352 (15) | 0.0120 (11) | 0.0137 (11) | 0.0106 (12) |
C31 | 0.0262 (12) | 0.0229 (12) | 0.0217 (12) | 0.0087 (9) | 0.0043 (9) | 0.0071 (10) |
C32 | 0.0337 (13) | 0.0306 (14) | 0.0249 (13) | 0.0136 (11) | 0.0102 (10) | 0.0073 (11) |
C33 | 0.0301 (13) | 0.0406 (16) | 0.0408 (16) | 0.0113 (12) | 0.0139 (12) | 0.0149 (13) |
C34 | 0.0314 (13) | 0.0295 (14) | 0.0448 (17) | 0.0039 (11) | 0.0003 (12) | 0.0110 (13) |
C35 | 0.0387 (15) | 0.0271 (14) | 0.0330 (15) | 0.0105 (11) | 0.0021 (12) | 0.0030 (12) |
C36 | 0.0318 (13) | 0.0278 (13) | 0.0244 (13) | 0.0114 (10) | 0.0094 (10) | 0.0068 (10) |
Sn1—C11 | 2.138 (2) | C14—C15 | 1.375 (4) |
Sn1—C21 | 2.139 (2) | C14—H14 | 0.9500 |
Sn1—C31 | 2.142 (2) | C15—C16 | 1.389 (4) |
Sn1—C7 | 2.172 (2) | C15—H15 | 0.9500 |
N1—O2 | 1.223 (3) | C16—H16 | 0.9500 |
N1—O1 | 1.228 (3) | C21—C22 | 1.388 (4) |
N1—C4 | 1.464 (3) | C21—C26 | 1.405 (4) |
C1—C2 | 1.397 (3) | C22—C23 | 1.383 (4) |
C1—C6 | 1.403 (3) | C22—H22 | 0.9500 |
C1—S1 | 1.757 (2) | C23—C24 | 1.385 (4) |
C2—C3 | 1.382 (3) | C23—H23 | 0.9500 |
C2—H2 | 0.9500 | C24—C25 | 1.375 (4) |
C3—C4 | 1.379 (3) | C24—H24 | 0.9500 |
C3—H3 | 0.9500 | C25—C26 | 1.386 (4) |
C4—C5 | 1.385 (3) | C25—H25 | 0.9500 |
C5—C6 | 1.370 (3) | C26—H26 | 0.9500 |
C5—H5 | 0.9500 | C31—C36 | 1.394 (3) |
C6—H6 | 0.9500 | C31—C32 | 1.399 (3) |
S1—C7 | 1.780 (3) | C32—C33 | 1.380 (4) |
C7—H1A | 0.9900 | C32—H32 | 0.9500 |
C7—H1B | 0.9900 | C33—C34 | 1.389 (4) |
C11—C12 | 1.392 (3) | C33—H33 | 0.9500 |
C11—C16 | 1.392 (3) | C34—C35 | 1.379 (4) |
C12—C13 | 1.388 (3) | C34—H34 | 0.9500 |
C12—H12 | 0.9500 | C35—C36 | 1.384 (4) |
C13—C14 | 1.379 (4) | C35—H35 | 0.9500 |
C13—H13 | 0.9500 | C36—H36 | 0.9500 |
C11—Sn1—C21 | 107.46 (9) | C15—C14—H14 | 120.1 |
C11—Sn1—C31 | 114.64 (8) | C13—C14—H14 | 120.1 |
C21—Sn1—C31 | 108.01 (9) | C14—C15—C16 | 120.1 (2) |
C11—Sn1—C7 | 113.69 (9) | C14—C15—H15 | 119.9 |
C21—Sn1—C7 | 106.27 (10) | C16—C15—H15 | 119.9 |
C31—Sn1—C7 | 106.36 (9) | C15—C16—C11 | 120.9 (2) |
O2—N1—O1 | 123.1 (2) | C15—C16—H16 | 119.6 |
O2—N1—C4 | 118.0 (2) | C11—C16—H16 | 119.6 |
O1—N1—C4 | 118.9 (2) | C22—C21—C26 | 117.7 (2) |
C2—C1—C6 | 118.9 (2) | C22—C21—Sn1 | 120.07 (18) |
C2—C1—S1 | 124.66 (18) | C26—C21—Sn1 | 122.14 (19) |
C6—C1—S1 | 116.38 (18) | C23—C22—C21 | 121.5 (3) |
C3—C2—C1 | 120.2 (2) | C23—C22—H22 | 119.2 |
C3—C2—H2 | 119.9 | C21—C22—H22 | 119.2 |
C1—C2—H2 | 119.9 | C22—C23—C24 | 119.7 (3) |
C4—C3—C2 | 119.3 (2) | C22—C23—H23 | 120.1 |
C4—C3—H3 | 120.4 | C24—C23—H23 | 120.1 |
C2—C3—H3 | 120.4 | C25—C24—C23 | 120.1 (3) |
C3—C4—C5 | 121.7 (2) | C25—C24—H24 | 120.0 |
C3—C4—N1 | 118.9 (2) | C23—C24—H24 | 120.0 |
C5—C4—N1 | 119.4 (2) | C24—C25—C26 | 120.2 (3) |
C6—C5—C4 | 118.8 (2) | C24—C25—H25 | 119.9 |
C6—C5—H5 | 120.6 | C26—C25—H25 | 119.9 |
C4—C5—H5 | 120.6 | C25—C26—C21 | 120.7 (3) |
C5—C6—C1 | 120.9 (2) | C25—C26—H26 | 119.6 |
C5—C6—H6 | 119.5 | C21—C26—H26 | 119.6 |
C1—C6—H6 | 119.5 | C36—C31—C32 | 118.0 (2) |
C1—S1—C7 | 104.14 (11) | C36—C31—Sn1 | 119.67 (17) |
S1—C7—Sn1 | 114.11 (12) | C32—C31—Sn1 | 122.30 (18) |
S1—C7—H1A | 108.7 | C33—C32—C31 | 120.7 (2) |
Sn1—C7—H1A | 108.7 | C33—C32—H32 | 119.7 |
S1—C7—H1B | 108.7 | C31—C32—H32 | 119.7 |
Sn1—C7—H1B | 108.7 | C32—C33—C34 | 120.6 (2) |
H1A—C7—H1B | 107.6 | C32—C33—H33 | 119.7 |
C12—C11—C16 | 118.2 (2) | C34—C33—H33 | 119.7 |
C12—C11—Sn1 | 122.70 (17) | C35—C34—C33 | 119.2 (2) |
C16—C11—Sn1 | 119.14 (18) | C35—C34—H34 | 120.4 |
C13—C12—C11 | 120.8 (2) | C33—C34—H34 | 120.4 |
C13—C12—H12 | 119.6 | C34—C35—C36 | 120.4 (2) |
C11—C12—H12 | 119.6 | C34—C35—H35 | 119.8 |
C14—C13—C12 | 120.2 (2) | C36—C35—H35 | 119.8 |
C14—C13—H13 | 119.9 | C35—C36—C31 | 121.0 (2) |
C12—C13—H13 | 119.9 | C35—C36—H36 | 119.5 |
C15—C14—C13 | 119.9 (2) | C31—C36—H36 | 119.5 |
C6—C1—C2—C3 | 1.8 (4) | C14—C15—C16—C11 | 0.1 (4) |
S1—C1—C2—C3 | −176.10 (19) | C12—C11—C16—C15 | 0.4 (4) |
C1—C2—C3—C4 | −1.4 (4) | Sn1—C11—C16—C15 | −179.5 (2) |
C2—C3—C4—C5 | −0.1 (4) | C11—Sn1—C21—C22 | −54.5 (2) |
C2—C3—C4—N1 | 179.7 (2) | C31—Sn1—C21—C22 | −178.66 (18) |
O2—N1—C4—C3 | 0.9 (3) | C7—Sn1—C21—C22 | 67.5 (2) |
O1—N1—C4—C3 | −178.0 (2) | C11—Sn1—C21—C26 | 128.19 (19) |
O2—N1—C4—C5 | −179.3 (2) | C31—Sn1—C21—C26 | 4.0 (2) |
O1—N1—C4—C5 | 1.7 (3) | C7—Sn1—C21—C26 | −109.77 (19) |
C3—C4—C5—C6 | 1.2 (4) | C26—C21—C22—C23 | 0.1 (4) |
N1—C4—C5—C6 | −178.6 (2) | Sn1—C21—C22—C23 | −177.3 (2) |
C4—C5—C6—C1 | −0.8 (4) | C21—C22—C23—C24 | 0.0 (4) |
C2—C1—C6—C5 | −0.7 (4) | C22—C23—C24—C25 | −0.3 (4) |
S1—C1—C6—C5 | 177.3 (2) | C23—C24—C25—C26 | 0.3 (4) |
C2—C1—S1—C7 | −6.8 (2) | C24—C25—C26—C21 | −0.2 (4) |
C6—C1—S1—C7 | 175.30 (19) | C22—C21—C26—C25 | −0.1 (4) |
C1—S1—C7—Sn1 | 168.41 (13) | Sn1—C21—C26—C25 | 177.31 (19) |
C11—Sn1—C7—S1 | 13.80 (18) | C11—Sn1—C31—C36 | 136.06 (18) |
C21—Sn1—C7—S1 | −104.19 (15) | C21—Sn1—C31—C36 | −104.20 (19) |
C31—Sn1—C7—S1 | 140.90 (13) | C7—Sn1—C31—C36 | 9.5 (2) |
C21—Sn1—C11—C12 | 142.3 (2) | C11—Sn1—C31—C32 | −44.0 (2) |
C31—Sn1—C11—C12 | −97.7 (2) | C21—Sn1—C31—C32 | 75.7 (2) |
C7—Sn1—C11—C12 | 25.0 (2) | C7—Sn1—C31—C32 | −170.57 (19) |
C21—Sn1—C11—C16 | −37.7 (2) | C36—C31—C32—C33 | −1.0 (4) |
C31—Sn1—C11—C16 | 82.3 (2) | Sn1—C31—C32—C33 | 179.12 (19) |
C7—Sn1—C11—C16 | −155.04 (19) | C31—C32—C33—C34 | 0.7 (4) |
C16—C11—C12—C13 | −0.8 (4) | C32—C33—C34—C35 | −0.1 (4) |
Sn1—C11—C12—C13 | 179.18 (19) | C33—C34—C35—C36 | −0.1 (4) |
C11—C12—C13—C14 | 0.6 (4) | C34—C35—C36—C31 | −0.2 (4) |
C12—C13—C14—C15 | 0.0 (4) | C32—C31—C36—C35 | 0.8 (4) |
C13—C14—C15—C16 | −0.3 (4) | Sn1—C31—C36—C35 | −179.34 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.95 | 2.56 | 3.151 (3) | 121 |
C36—H36···O2ii | 0.95 | 2.57 | 3.439 (3) | 152 |
Symmetry codes: (i) −x+3, −y+2, −z; (ii) −x+2, −y+1, −z. |
[Sn(C6H5)3(C7H6NO4S)] | Z = 2 |
Mr = 550.18 | F(000) = 552 |
Triclinic, P1 | Dx = 1.606 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8715 (4) Å | Cell parameters from 10598 reflections |
b = 9.9680 (5) Å | θ = 2.3–28.9° |
c = 17.6403 (10) Å | µ = 1.25 mm−1 |
α = 81.0264 (19)° | T = 120 K |
β = 89.4798 (19)° | Block, colourless |
γ = 72.5146 (17)° | 0.5 × 0.3 × 0.3 mm |
V = 1137.42 (11) Å3 |
Bruker SMART CCD area-detector diffractometer | 5261 independent reflections |
Radiation source: fine-focus sealed tube | 5061 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.011 |
ϕ/ω scans | θmax = 28.9°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −9→8 |
Tmin = 0.674, Tmax = 0.688 | k = −13→13 |
10598 measured reflections | l = −23→23 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.018 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.046 | H-atom parameters constrained |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0246P)2 + 0.5422P] where P = (Fo2 + 2Fc2)/3 |
5261 reflections | (Δ/σ)max = 0.002 |
289 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.61 e Å−3 |
[Sn(C6H5)3(C7H6NO4S)] | γ = 72.5146 (17)° |
Mr = 550.18 | V = 1137.42 (11) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.8715 (4) Å | Mo Kα radiation |
b = 9.9680 (5) Å | µ = 1.25 mm−1 |
c = 17.6403 (10) Å | T = 120 K |
α = 81.0264 (19)° | 0.5 × 0.3 × 0.3 mm |
β = 89.4798 (19)° |
Bruker SMART CCD area-detector diffractometer | 5261 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 5061 reflections with I > 2σ(I) |
Tmin = 0.674, Tmax = 0.688 | Rint = 0.011 |
10598 measured reflections |
R[F2 > 2σ(F2)] = 0.018 | 0 restraints |
wR(F2) = 0.046 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.38 e Å−3 |
5261 reflections | Δρmin = −0.61 e Å−3 |
289 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. 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. |
x | y | z | Uiso*/Ueq | ||
N1 | −0.1272 (2) | 0.78849 (14) | −0.07945 (7) | 0.0229 (3) | |
O1 | −0.1909 (2) | 0.68648 (14) | −0.07962 (8) | 0.0338 (3) | |
O2 | −0.21350 (19) | 0.90812 (13) | −0.11411 (7) | 0.0320 (3) | |
C1 | 0.4041 (2) | 0.73397 (15) | 0.05258 (8) | 0.0173 (3) | |
C2 | 0.3224 (2) | 0.86023 (16) | 0.00211 (8) | 0.0200 (3) | |
H2 | 0.3849 | 0.9339 | −0.0018 | 0.024* | |
C3 | 0.1485 (2) | 0.87784 (16) | −0.04253 (8) | 0.0200 (3) | |
H3 | 0.0903 | 0.9632 | −0.0776 | 0.024* | |
C4 | 0.0622 (2) | 0.76800 (16) | −0.03473 (8) | 0.0190 (3) | |
C5 | 0.1449 (3) | 0.64027 (17) | 0.01373 (10) | 0.0260 (3) | |
H5 | 0.0838 | 0.5659 | 0.0167 | 0.031* | |
C6 | 0.3187 (2) | 0.62317 (16) | 0.05790 (9) | 0.0240 (3) | |
H6 | 0.3792 | 0.5363 | 0.0916 | 0.029* | |
S1 | 0.61069 (5) | 0.71692 (4) | 0.11706 (2) | 0.01771 (7) | |
O3 | 0.72525 (18) | 0.56815 (12) | 0.13397 (7) | 0.0288 (3) | |
O4 | 0.71512 (17) | 0.81764 (13) | 0.08552 (6) | 0.0258 (2) | |
C7 | 0.4902 (2) | 0.77127 (17) | 0.19955 (8) | 0.0203 (3) | |
H7A | 0.4147 | 0.7040 | 0.2202 | 0.024* | |
H7B | 0.3886 | 0.8662 | 0.1848 | 0.024* | |
Sn1 | 0.693023 (14) | 0.783753 (10) | 0.290829 (5) | 0.01694 (4) | |
C11 | 0.7754 (2) | 0.97516 (15) | 0.26859 (8) | 0.0191 (3) | |
C12 | 0.6574 (2) | 1.09512 (17) | 0.21877 (9) | 0.0237 (3) | |
H12 | 0.5391 | 1.0913 | 0.1929 | 0.028* | |
C13 | 0.7128 (3) | 1.21997 (17) | 0.20701 (10) | 0.0272 (3) | |
H13 | 0.6330 | 1.3002 | 0.1724 | 0.033* | |
C14 | 0.8821 (3) | 1.22852 (18) | 0.24508 (10) | 0.0304 (4) | |
H14 | 0.9175 | 1.3146 | 0.2375 | 0.036* | |
C15 | 1.0006 (3) | 1.1101 (2) | 0.29464 (11) | 0.0333 (4) | |
H15 | 1.1177 | 1.1152 | 0.3208 | 0.040* | |
C16 | 0.9482 (3) | 0.98432 (18) | 0.30605 (10) | 0.0271 (3) | |
H16 | 1.0308 | 0.9037 | 0.3397 | 0.033* | |
C21 | 0.4997 (2) | 0.78970 (16) | 0.38663 (8) | 0.0195 (3) | |
C22 | 0.4313 (2) | 0.91175 (17) | 0.42094 (9) | 0.0252 (3) | |
H22 | 0.4759 | 0.9920 | 0.4028 | 0.030* | |
C23 | 0.2987 (3) | 0.9176 (2) | 0.48136 (10) | 0.0320 (4) | |
H23 | 0.2517 | 1.0021 | 0.5035 | 0.038* | |
C24 | 0.2353 (3) | 0.8006 (2) | 0.50912 (10) | 0.0334 (4) | |
H24 | 0.1465 | 0.8039 | 0.5508 | 0.040* | |
C25 | 0.3016 (3) | 0.6788 (2) | 0.47588 (10) | 0.0319 (4) | |
H25 | 0.2584 | 0.5984 | 0.4949 | 0.038* | |
C26 | 0.4316 (3) | 0.67337 (17) | 0.41457 (9) | 0.0252 (3) | |
H26 | 0.4742 | 0.5897 | 0.3916 | 0.030* | |
C31 | 0.9550 (2) | 0.59999 (16) | 0.31201 (9) | 0.0197 (3) | |
C32 | 0.9942 (3) | 0.51393 (17) | 0.38376 (9) | 0.0260 (3) | |
H32 | 0.9016 | 0.5365 | 0.4235 | 0.031* | |
C33 | 1.1671 (3) | 0.39519 (18) | 0.39821 (10) | 0.0305 (4) | |
H33 | 1.1916 | 0.3376 | 0.4475 | 0.037* | |
C34 | 1.3028 (3) | 0.36128 (18) | 0.34098 (11) | 0.0314 (4) | |
H34 | 1.4209 | 0.2806 | 0.3506 | 0.038* | |
C35 | 1.2653 (3) | 0.4461 (2) | 0.26909 (11) | 0.0363 (4) | |
H35 | 1.3582 | 0.4231 | 0.2295 | 0.044* | |
C36 | 1.0928 (3) | 0.56447 (19) | 0.25470 (10) | 0.0285 (3) | |
H36 | 1.0687 | 0.6216 | 0.2053 | 0.034* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0218 (6) | 0.0249 (6) | 0.0209 (6) | −0.0054 (5) | −0.0037 (5) | −0.0037 (5) |
O1 | 0.0329 (6) | 0.0313 (6) | 0.0402 (7) | −0.0157 (5) | −0.0134 (5) | −0.0024 (5) |
O2 | 0.0284 (6) | 0.0270 (6) | 0.0354 (7) | −0.0029 (5) | −0.0130 (5) | 0.0009 (5) |
C1 | 0.0167 (6) | 0.0192 (6) | 0.0161 (6) | −0.0056 (5) | −0.0005 (5) | −0.0031 (5) |
C2 | 0.0217 (7) | 0.0196 (7) | 0.0197 (7) | −0.0090 (6) | 0.0009 (5) | −0.0008 (5) |
C3 | 0.0213 (7) | 0.0191 (7) | 0.0176 (7) | −0.0050 (6) | −0.0002 (5) | 0.0002 (5) |
C4 | 0.0183 (7) | 0.0215 (7) | 0.0171 (6) | −0.0054 (5) | −0.0020 (5) | −0.0038 (5) |
C5 | 0.0293 (8) | 0.0209 (7) | 0.0299 (8) | −0.0124 (6) | −0.0088 (6) | 0.0000 (6) |
C6 | 0.0270 (8) | 0.0183 (7) | 0.0259 (8) | −0.0083 (6) | −0.0082 (6) | 0.0026 (6) |
S1 | 0.01634 (16) | 0.01868 (16) | 0.01827 (16) | −0.00573 (13) | −0.00165 (12) | −0.00247 (12) |
O3 | 0.0266 (6) | 0.0206 (5) | 0.0348 (6) | 0.0001 (4) | −0.0111 (5) | −0.0056 (5) |
O4 | 0.0236 (5) | 0.0337 (6) | 0.0243 (6) | −0.0163 (5) | 0.0011 (4) | −0.0023 (5) |
C7 | 0.0190 (7) | 0.0259 (7) | 0.0167 (6) | −0.0079 (6) | −0.0002 (5) | −0.0029 (5) |
Sn1 | 0.01711 (5) | 0.01794 (5) | 0.01597 (5) | −0.00640 (4) | −0.00087 (3) | −0.00107 (4) |
C11 | 0.0206 (7) | 0.0187 (7) | 0.0180 (7) | −0.0062 (5) | 0.0020 (5) | −0.0025 (5) |
C12 | 0.0204 (7) | 0.0246 (7) | 0.0228 (7) | −0.0031 (6) | 0.0006 (6) | −0.0016 (6) |
C13 | 0.0300 (8) | 0.0186 (7) | 0.0268 (8) | 0.0000 (6) | 0.0081 (6) | −0.0004 (6) |
C14 | 0.0413 (10) | 0.0202 (7) | 0.0331 (9) | −0.0137 (7) | 0.0102 (7) | −0.0060 (6) |
C15 | 0.0368 (9) | 0.0317 (9) | 0.0362 (9) | −0.0191 (8) | −0.0064 (7) | −0.0018 (7) |
C16 | 0.0284 (8) | 0.0245 (8) | 0.0280 (8) | −0.0104 (6) | −0.0072 (6) | 0.0022 (6) |
C21 | 0.0179 (7) | 0.0228 (7) | 0.0174 (6) | −0.0061 (5) | −0.0018 (5) | −0.0019 (5) |
C22 | 0.0241 (7) | 0.0250 (7) | 0.0281 (8) | −0.0085 (6) | −0.0021 (6) | −0.0062 (6) |
C23 | 0.0250 (8) | 0.0417 (10) | 0.0309 (9) | −0.0064 (7) | 0.0009 (7) | −0.0179 (7) |
C24 | 0.0237 (8) | 0.0543 (11) | 0.0225 (8) | −0.0120 (8) | 0.0037 (6) | −0.0069 (7) |
C25 | 0.0316 (9) | 0.0389 (9) | 0.0261 (8) | −0.0164 (8) | 0.0028 (7) | 0.0030 (7) |
C26 | 0.0277 (8) | 0.0236 (7) | 0.0250 (8) | −0.0096 (6) | 0.0017 (6) | −0.0024 (6) |
C31 | 0.0184 (7) | 0.0194 (7) | 0.0222 (7) | −0.0078 (5) | −0.0020 (5) | −0.0023 (5) |
C32 | 0.0278 (8) | 0.0249 (8) | 0.0233 (7) | −0.0073 (6) | 0.0003 (6) | 0.0003 (6) |
C33 | 0.0355 (9) | 0.0238 (8) | 0.0280 (8) | −0.0070 (7) | −0.0064 (7) | 0.0053 (6) |
C34 | 0.0263 (8) | 0.0225 (8) | 0.0401 (10) | −0.0011 (6) | −0.0053 (7) | −0.0017 (7) |
C35 | 0.0273 (9) | 0.0390 (10) | 0.0336 (9) | 0.0022 (7) | 0.0061 (7) | −0.0035 (8) |
C36 | 0.0237 (8) | 0.0326 (8) | 0.0241 (8) | −0.0043 (7) | 0.0016 (6) | 0.0017 (6) |
N1—O1 | 1.2222 (18) | C13—C14 | 1.380 (3) |
N1—O2 | 1.2254 (18) | C13—H13 | 0.9500 |
N1—C4 | 1.4721 (19) | C14—C15 | 1.390 (3) |
C1—C2 | 1.388 (2) | C14—H14 | 0.9500 |
C1—C6 | 1.389 (2) | C15—C16 | 1.391 (2) |
C1—S1 | 1.7782 (14) | C15—H15 | 0.9500 |
C2—C3 | 1.388 (2) | C16—H16 | 0.9500 |
C2—H2 | 0.9500 | C21—C22 | 1.396 (2) |
C3—C4 | 1.382 (2) | C21—C26 | 1.397 (2) |
C3—H3 | 0.9500 | C22—C23 | 1.393 (2) |
C4—C5 | 1.382 (2) | C22—H22 | 0.9500 |
C5—C6 | 1.384 (2) | C23—C24 | 1.383 (3) |
C5—H5 | 0.9500 | C23—H23 | 0.9500 |
C6—H6 | 0.9500 | C24—C25 | 1.382 (3) |
S1—O3 | 1.4396 (12) | C24—H24 | 0.9500 |
S1—O4 | 1.4435 (11) | C25—C26 | 1.393 (2) |
S1—C7 | 1.7469 (15) | C25—H25 | 0.9500 |
O3—Sn1 | 3.7259 (12) | C26—H26 | 0.9500 |
O4—Sn1 | 3.5906 (12) | C31—C36 | 1.392 (2) |
C7—Sn1 | 2.1815 (14) | C31—C32 | 1.392 (2) |
C7—H7A | 0.9900 | C32—C33 | 1.394 (2) |
C7—H7B | 0.9900 | C32—H32 | 0.9500 |
Sn1—C11 | 2.1275 (15) | C33—C34 | 1.379 (3) |
Sn1—C31 | 2.1337 (15) | C33—H33 | 0.9500 |
Sn1—C21 | 2.1371 (15) | C34—C35 | 1.389 (3) |
C11—C16 | 1.397 (2) | C34—H34 | 0.9500 |
C11—C12 | 1.401 (2) | C35—C36 | 1.390 (2) |
C12—C13 | 1.392 (2) | C35—H35 | 0.9500 |
C12—H12 | 0.9500 | C36—H36 | 0.9500 |
O1—N1—O2 | 123.57 (13) | C12—C11—Sn1 | 121.78 (11) |
O1—N1—C4 | 118.67 (13) | C13—C12—C11 | 120.33 (15) |
O2—N1—C4 | 117.76 (13) | C13—C12—H12 | 119.8 |
C2—C1—C6 | 121.38 (13) | C11—C12—H12 | 119.8 |
C2—C1—S1 | 119.84 (11) | C14—C13—C12 | 120.73 (15) |
C6—C1—S1 | 118.62 (11) | C14—C13—H13 | 119.6 |
C3—C2—C1 | 119.40 (13) | C12—C13—H13 | 119.6 |
C3—C2—H2 | 120.3 | C13—C14—C15 | 119.48 (15) |
C1—C2—H2 | 120.3 | C13—C14—H14 | 120.3 |
C4—C3—C2 | 118.34 (13) | C15—C14—H14 | 120.3 |
C4—C3—H3 | 120.8 | C14—C15—C16 | 120.26 (16) |
C2—C3—H3 | 120.8 | C14—C15—H15 | 119.9 |
C5—C4—C3 | 122.90 (14) | C16—C15—H15 | 119.9 |
C5—C4—N1 | 118.52 (13) | C15—C16—C11 | 120.71 (15) |
C3—C4—N1 | 118.57 (13) | C15—C16—H16 | 119.6 |
C4—C5—C6 | 118.46 (14) | C11—C16—H16 | 119.6 |
C4—C5—H5 | 120.8 | C22—C21—C26 | 118.17 (14) |
C6—C5—H5 | 120.8 | C22—C21—Sn1 | 121.02 (11) |
C5—C6—C1 | 119.46 (14) | C26—C21—Sn1 | 120.76 (11) |
C5—C6—H6 | 120.3 | C23—C22—C21 | 121.02 (15) |
C1—C6—H6 | 120.3 | C23—C22—H22 | 119.5 |
O3—S1—O4 | 118.72 (7) | C21—C22—H22 | 119.5 |
O3—S1—C7 | 109.20 (8) | C24—C23—C22 | 120.04 (16) |
O4—S1—C7 | 108.46 (7) | C24—C23—H23 | 120.0 |
O3—S1—C1 | 107.67 (7) | C22—C23—H23 | 120.0 |
O4—S1—C1 | 108.16 (7) | C25—C24—C23 | 119.71 (16) |
C7—S1—C1 | 103.56 (7) | C25—C24—H24 | 120.1 |
S1—O3—Sn1 | 62.83 (4) | C23—C24—H24 | 120.1 |
S1—O4—Sn1 | 67.78 (4) | C24—C25—C26 | 120.43 (16) |
S1—C7—Sn1 | 115.20 (7) | C24—C25—H25 | 119.8 |
S1—C7—H7A | 108.5 | C26—C25—H25 | 119.8 |
Sn1—C7—H7A | 108.5 | C25—C26—C21 | 120.62 (15) |
S1—C7—H7B | 108.5 | C25—C26—H26 | 119.7 |
Sn1—C7—H7B | 108.5 | C21—C26—H26 | 119.7 |
H7A—C7—H7B | 107.5 | C36—C31—C32 | 118.34 (14) |
C11—Sn1—C31 | 111.76 (6) | C36—C31—Sn1 | 120.73 (11) |
C11—Sn1—C21 | 109.81 (6) | C32—C31—Sn1 | 120.92 (11) |
C31—Sn1—C21 | 110.02 (6) | C31—C32—C33 | 121.08 (16) |
C11—Sn1—C7 | 111.36 (6) | C31—C32—H32 | 119.5 |
C31—Sn1—C7 | 112.24 (6) | C33—C32—H32 | 119.5 |
C21—Sn1—C7 | 101.15 (5) | C34—C33—C32 | 120.03 (16) |
C11—Sn1—O4 | 81.13 (4) | C34—C33—H33 | 120.0 |
C31—Sn1—O4 | 94.52 (5) | C32—C33—H33 | 120.0 |
C21—Sn1—O4 | 145.61 (4) | C33—C34—C35 | 119.48 (16) |
C7—Sn1—O4 | 45.81 (4) | C33—C34—H34 | 120.3 |
C11—Sn1—O3 | 118.94 (4) | C35—C34—H34 | 120.3 |
C31—Sn1—O3 | 70.62 (4) | C34—C35—C36 | 120.48 (17) |
C21—Sn1—O3 | 126.99 (4) | C34—C35—H35 | 119.8 |
C7—Sn1—O3 | 43.14 (4) | C36—C35—H35 | 119.8 |
O4—Sn1—O3 | 39.58 (3) | C35—C36—C31 | 120.59 (16) |
C16—C11—C12 | 118.48 (14) | C35—C36—H36 | 119.7 |
C16—C11—Sn1 | 119.72 (11) | C31—C36—H36 | 119.7 |
C6—C1—C2—C3 | 1.8 (2) | C31—Sn1—C11—C12 | 147.86 (12) |
S1—C1—C2—C3 | −173.58 (11) | C21—Sn1—C11—C12 | −89.75 (13) |
C1—C2—C3—C4 | 0.2 (2) | C7—Sn1—C11—C12 | 21.44 (14) |
C2—C3—C4—C5 | −2.0 (2) | O4—Sn1—C11—C12 | 56.51 (12) |
C2—C3—C4—N1 | 177.39 (13) | O3—Sn1—C11—C12 | 68.67 (13) |
O1—N1—C4—C5 | −9.0 (2) | C16—C11—C12—C13 | 0.2 (2) |
O2—N1—C4—C5 | 170.43 (15) | Sn1—C11—C12—C13 | 178.33 (11) |
O1—N1—C4—C3 | 171.62 (14) | C11—C12—C13—C14 | −1.1 (2) |
O2—N1—C4—C3 | −9.0 (2) | C12—C13—C14—C15 | 1.2 (3) |
C3—C4—C5—C6 | 1.8 (3) | C13—C14—C15—C16 | −0.3 (3) |
N1—C4—C5—C6 | −177.62 (15) | C14—C15—C16—C11 | −0.6 (3) |
C4—C5—C6—C1 | 0.2 (3) | C12—C11—C16—C15 | 0.6 (2) |
C2—C1—C6—C5 | −2.0 (2) | Sn1—C11—C16—C15 | −177.53 (14) |
S1—C1—C6—C5 | 173.40 (13) | C11—Sn1—C21—C22 | 5.31 (14) |
C2—C1—S1—O3 | −152.70 (12) | C31—Sn1—C21—C22 | 128.72 (12) |
C6—C1—S1—O3 | 31.82 (14) | C7—Sn1—C21—C22 | −112.44 (12) |
C2—C1—S1—O4 | −23.25 (14) | O4—Sn1—C21—C22 | −98.35 (13) |
C6—C1—S1—O4 | 161.27 (12) | O3—Sn1—C21—C22 | −150.93 (10) |
C2—C1—S1—C7 | 91.70 (13) | C11—Sn1—C21—C26 | −177.36 (12) |
C6—C1—S1—C7 | −83.77 (13) | C31—Sn1—C21—C26 | −53.95 (13) |
O4—S1—O3—Sn1 | 90.80 (6) | C7—Sn1—C21—C26 | 64.89 (13) |
C7—S1—O3—Sn1 | −34.18 (5) | O4—Sn1—C21—C26 | 78.98 (15) |
C1—S1—O3—Sn1 | −145.99 (6) | O3—Sn1—C21—C26 | 26.40 (14) |
O3—S1—O4—Sn1 | −94.34 (6) | C26—C21—C22—C23 | 0.0 (2) |
C7—S1—O4—Sn1 | 30.99 (5) | Sn1—C21—C22—C23 | 177.37 (12) |
C1—S1—O4—Sn1 | 142.69 (5) | C21—C22—C23—C24 | 1.0 (3) |
O3—S1—C7—Sn1 | 70.63 (9) | C22—C23—C24—C25 | −1.0 (3) |
O4—S1—C7—Sn1 | −60.12 (9) | C23—C24—C25—C26 | −0.1 (3) |
C1—S1—C7—Sn1 | −174.87 (7) | C24—C25—C26—C21 | 1.1 (3) |
S1—C7—Sn1—C11 | 79.80 (9) | C22—C21—C26—C25 | −1.1 (2) |
S1—C7—Sn1—C31 | −46.36 (10) | Sn1—C21—C26—C25 | −178.46 (12) |
S1—C7—Sn1—C21 | −163.59 (8) | C11—Sn1—C31—C36 | −64.63 (14) |
S1—C7—Sn1—O4 | 27.46 (5) | C21—Sn1—C31—C36 | 173.10 (12) |
S1—C7—Sn1—O3 | −30.23 (5) | C7—Sn1—C31—C36 | 61.31 (14) |
S1—O4—Sn1—C11 | −164.80 (6) | O4—Sn1—C31—C36 | 17.61 (13) |
S1—O4—Sn1—C31 | 83.85 (6) | O3—Sn1—C31—C36 | 49.69 (12) |
S1—O4—Sn1—C21 | −52.51 (10) | C11—Sn1—C31—C32 | 114.35 (13) |
S1—O4—Sn1—C7 | −33.05 (7) | C21—Sn1—C31—C32 | −7.91 (14) |
S1—O4—Sn1—O3 | 32.02 (4) | C7—Sn1—C31—C32 | −119.71 (12) |
S1—O3—Sn1—C11 | −52.65 (7) | O4—Sn1—C31—C32 | −163.41 (12) |
S1—O3—Sn1—C31 | −157.40 (7) | O3—Sn1—C31—C32 | −131.33 (13) |
S1—O3—Sn1—C21 | 101.67 (7) | C36—C31—C32—C33 | 0.2 (2) |
S1—O3—Sn1—C7 | 38.42 (7) | Sn1—C31—C32—C33 | −178.85 (13) |
S1—O3—Sn1—O4 | −33.59 (4) | C31—C32—C33—C34 | 0.0 (3) |
C31—Sn1—C11—C16 | −34.07 (14) | C32—C33—C34—C35 | −0.1 (3) |
C21—Sn1—C11—C16 | 88.32 (13) | C33—C34—C35—C36 | 0.1 (3) |
C7—Sn1—C11—C16 | −160.48 (12) | C34—C35—C36—C31 | 0.1 (3) |
O4—Sn1—C11—C16 | −125.42 (13) | C32—C31—C36—C35 | −0.2 (3) |
O3—Sn1—C11—C16 | −113.26 (12) | Sn1—C31—C36—C35 | 178.83 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O4i | 0.95 | 2.58 | 3.2753 (19) | 131 |
C5—H5···O1ii | 0.95 | 2.48 | 3.204 (2) | 133 |
C7—H7B···O2iii | 0.99 | 2.36 | 3.3163 (19) | 161 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z. |
Experimental details
(I) | (II) | |
Crystal data | ||
Chemical formula | [Sn(C6H5)3(C7H6NO2S)] | [Sn(C6H5)3(C7H6NO4S)] |
Mr | 518.18 | 550.18 |
Crystal system, space group | Triclinic, P1 | Triclinic, P1 |
Temperature (K) | 150 | 120 |
a, b, c (Å) | 6.6442 (1), 10.3070 (2), 17.2597 (4) | 6.8715 (4), 9.9680 (5), 17.6403 (10) |
α, β, γ (°) | 100.3385 (8), 98.6403 (9), 103.6969 (16) | 81.0264 (19), 89.4798 (19), 72.5146 (17) |
V (Å3) | 1106.51 (4) | 1137.42 (11) |
Z | 2 | 2 |
Radiation type | Mo Kα | Mo Kα |
µ (mm−1) | 1.27 | 1.25 |
Crystal size (mm) | 0.40 × 0.10 × 0.03 | 0.5 × 0.3 × 0.3 |
Data collection | ||
Diffractometer | Nonius KappaCCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SORTAV; Blessing, 1995, 1997) | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.817, 0.992 | 0.674, 0.688 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16551, 5030, 4460 | 10598, 5261, 5061 |
Rint | 0.052 | 0.011 |
(sin θ/λ)max (Å−1) | 0.649 | 0.679 |
Refinement | ||
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.079, 1.06 | 0.018, 0.046, 1.10 |
No. of reflections | 5030 | 5261 |
No. of parameters | 271 | 289 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.82, −1.39 | 0.38, −0.61 |
Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), SMART (Bruker, 1999), DENZO and COLLECT, SAINT (Bruker, 1999), SAINT, SHELXS86 (Sheldrick, 1990), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEX in OSCAIL (McArdle, 1994, 2000) and ORTEPIII for Windows (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
C5—H5···O1i | 0.95 | 2.56 | 3.151 (3) | 121 |
C36—H36···O2ii | 0.95 | 2.57 | 3.439 (3) | 152 |
Symmetry codes: (i) −x+3, −y+2, −z; (ii) −x+2, −y+1, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O4i | 0.95 | 2.58 | 3.2753 (19) | 131 |
C5—H5···O1ii | 0.95 | 2.48 | 3.204 (2) | 133 |
C7—H7B···O2iii | 0.99 | 2.36 | 3.3163 (19) | 161 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+1, −z; (iii) −x, −y+2, −z. |
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The intermolecular non-bonded interactions in a number of nitro, sulfido and sulfonyl aromatic derivatives have been investigated in the solid state (Kelly et al., 2002; Cannon et al., 2000, 2001; Glidewell et al., 2001; Wardell et al., 2000a,b). Continuating our studies, the structures of (4-nitrophenylsulfanylmethyl)triphenylstannane, (I), and (4-nitrophenylsulfonylmethyl)triphenylstannane, (II), have now been investigated and the results are presented here. \sch
Both (I) (Fig. 1) and (II) (Fig. 2) crystallize in the triclinic spacegroup P1 and form sheets via similar soft interactions. Molecules of (I) are linked by two different C—H···O hydrogen bonds (Table 1) into centrosymmetric dimers, where nitro O atoms act as acceptors. The phenyl atom C5 at (x,y,z) acts as a hydrogen-bond donor to nitro atom O1 at (3 - x, 2 - y, -z), thus forming a dimer characterized by an R22(10) motif with an inversion centre at (3/2,1,0). Similarly, atom C36 at (x,y,z) acts as a donor to nitro atom O2 at (2 - x, 1 - y, -z), giving an R22(24) ring with inversion centre at (1,1/2,0). These two dimers combine to form a sheet which propagates along [110] (Fig. 3). In addition, the phenyl rings of neighbouring molecules are weakly linked by C—H···π interactions. One of these interactions extends the sheet along the z direction; atom C15 at (x,y,z) donates to the C21—C26 phenyl ring at (1 - x, 2 - y, 1 - z), with a distance of 3.661 (3) Å between atom C15 and the ring centroid. Such dimers are shown in Fig. 4, and they have the effect of doubling the width of the sheets shown in Fig. 3.
Molecules of (II) are also linked via intermolecular C—H···O interactions. In this case, the sulfone group leads to one further bond (Table 2). Considering the nitro acceptor interactions first, phenyl atom C5 at (x,y,z) acts as a hydrogen-bond donor to nitro atom O1 at (-x, 1 - y, -z), to give an R22(10) motif centred at (0,1/2,0). Similarly, atom C7 at (x,y,z) donates to the nitro atom O2 at (-x, 2 - y, -z), giving an R22(18) ring centred at (0,1,0), forming a chain along [010] (Fig. 5). Thus, the effect of the sulfone group is to alter the local conformation and thus the C—H···O bonding to the second nitro O atom. In (I), a phenyl H atom from the Ph3Sn group acts as the donor, whereas in (II) the CH2 is the donor, effectively contracting the size of the R22(X) ring.
An extra hydrogen bond occurs due to the presence of the sulfone group. The phenyl atom C2 at (x,y,z) acts as a hydrogen-bond donor to the sulfone atom O4 at (1 - x, 2 - y, -z), forming an R22(10) motif with an inversion centre at (1/2,1,0). These three dimers thus combine to form a sheet which propagates along [110] (Fig. 6), as in the structure of (I).
As with (I), phenyl groups in (II) form C—H···π interactions with neighbouring molecules within the sheet. In addition, atom C33 at (x,y,z) donates a hydrogen bond to the C21—C26 phenyl ring at (2 - x, 1 - y, 1 - z), with a distance of 3.361 Å between the H atom and the centroid (Fig. 7), which, as in (I), has the effect of doubling the width of the sheet.
The Sn centre in (I) is four-coordinate; the bond angles, between 106.27 (10) and 114.64 (8)°, indicate a slightly distorted tetrahedral geometry. The Sn—C bond lengths are in the expected region and cover a narrow range, 2.138 (2)–2.172 (2) Å. The bond lengths in (II) show a greater range, with those involving the phenyl groups being between 2.1275 (15) and 2.1371 (15) Å, and the Sn—C-alkyl length being longer at 2.1815 (14) Å. The bond angles subtended at Sn in (II) range from 101.15 (5) to 111.76 (6)°, again indicative of a slightly distorted tetrahedral geometry. The closest Sn—Osulfone separation is Sn—O4 3.5906 (12) Å, a little within the sum of the van der Waals radii of 3.70 Å.
A number of related triphenyl-Sn and –Ge structures have been reported, along with one related iododiphenyltin compound (CSD database, Release?; Allen & Kennard, 1993). These are Ph3GeCH2SO2C6H5 (CSD refcode GESYIM; Howie & Wardell, 1997), Ph3Sn(CH2)2CH(SC6H4NO2-2)CH2Cl (ZIKHOQ; Aupers & Wardell, 1995), Ph3Sn(CH2)2SO2C6H4Me-4 [(III), n = 2, YEZVEE; Cox & Wardell, 1994), Ph3Sn(CH2)4SO2C6H4Me-4 [(III), n = 4, YEZVII; Cox & Wardell, 1994), Ph3Sn(CH2)3SO2C6H4Me-4 [(III), n = 3, ZAVHIN, Howie & Wardell, 1994), IPh2Sn(CH2)3SO2C6H4Me-4 (ZAVHOT; Howie & Wardell, 1994), Ph3SnCHClCH2SC6H3NO2-2-Me-4 (PAGHEK; Howie et al., 1992), Ph3SnCH(SCN)CH2SC6H4NO2-2 (PAGHIO; Howie et al., 1992), cyclohexyl3SnCH2SC6H4tBu-4 (JERMIC; Cox et al., 1990), Ph3Ge(CH2)SO2C6H5 (NOJXEP; Wardell & Cox, 1996), Ph3SnC(SMe)═ CHC6H5 (GODLOA and GODLUG; Bruhn et al., 1999), Ph3SnC(SCH2Ph)CHCHC(SCH2Ph)SnPh3 (POMXUK; Block et al., 1994) and Ph3SnCH2CH2SC6H4Me-4 (ZUWQIR; Cox et al., 1995).
Of these, the first four (GESYIM, ZIKHOQ, YEZVEE and YEZVII) have C—H···O bonds which can be considered in relation to (I) and (II). The latter four compounds (GODLOA, GODLUG, POMXUK and ZUWQIR) display C—H···S interactions, while the rest do not form hydrogen bonds as detected by PLATON (Spek, 2002).
Ph3GeCH2SO2C6H5 (GESYIM), a Ge analogue to (II), forms hydrogen bonds via the CH2 as donor to a sulfone O atom, thus forming simple C(4) chains along [001]. No rings are formed. Ph3Sn(CH2)2CH(SC6H4NO2-2)CH2Cl (ZIKHOQ), in which the nitro group is ortho to S, again has CH2 as the donor with one nitro O atom as acceptor, forming R22(16) dimers. The other H atom of the CH2 donates to the other nitro O atom, to form a chain of dimers along [001]. Ph3Sn(CH2)2SO2C6H4Me-4 (YEZVEE) again donates a hydrogen bond via the CH2 adjacent to S to a sulfone O atom; in addition, a phenyl H atom acts as a donor to the same O atom, forming R32(13) groups which link to give C(8) chains along [100]. In the related compound Ph3Sn(CH2)4SO2C6H4Me-4 (YEZVII), similar hydrogen bonding occurs, although here via the third CH2 group from S, to give an R32(16) motif, linking to give C(12) chains along [010]. Both motifs are enlarged by the extra CH2 groups in the latter compound.
The products of the reactions of ω-sulfidoalkylstannanes, R3Sn(CH2)nSR', with oxidants depend greatly on n and on the oxidant. For example, (II) was obtained by H2O2 oxidation of (I), whereas the reaction of the related compound, Ph3Sn(CH2)nSC6H4Me-4 [(IV), n = 1] with NaIO4 led to the cleavage of the molecule with formation of Ph3SnCH2I and 4-MeC6H4SO3H (Taylor & Wardell, 1976; see also Peterson, 1971). The use of 3-ClC6H4CO3H with (IV) with n = 1 also resulted in cleavage (Wardell, unpublished observation). In contrast, oxidations of (IV) with n = 3 or 4 proceeded readily to the sulfones (III) with n = 3 or 4, or the corresponding sulfoxides, depending on the molar ratios of the reagents (Wardell & Wigzell, 1983). Particularly sensitive to oxidants is (IV) with n = 2. The reaction of (IV) with n = 2 with either NaIO4 or 3-ClC6H4CO3H led to ethylene loss (Wardell & Wigzell, 1983). Compound (IV) with n = 2 was, however, obtained by the addition of Ph3SnH to H2C═CHSO2C6H4Me-4 (Wardell & Wigzell, 1983). A contrast between Ge and Sn compounds is clear from the reactions of Ph3MCH2SR' (M is Ge or Sn) with 3-ClC6H4CO3H or Br2. The Br2—R3SnCH2SR' reactions invariably result in Sn—C bond cleavage, while the Ge compounds can be oxidized to Ph3GeCH2SOmR (m = 1 or 2) by either Br2 in MeOH or 3-ClC6H4CO3H (Taylor & Wardell, 1976; Wardell & Cox, 1996).