Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802017993/ob6180sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802017993/ob6180Isup2.hkl |
CCDC reference: 200752
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean (C-C) = 0.003 Å
- R factor = 0.045
- wR factor = 0.116
- Data-to-parameter ratio = 13.6
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(9) - C(12) = 1.44 Ang. PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 3 C2 -SI1 -C4 -C5 18.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 4 C1 -SI1 -C4 -C5 7.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 5 C3 -SI1 -C4 -C5 5.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 6 SI1 -C4 -C5 -C6 3.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 9 SI1'-C4' -C5' -C6 -179.00 12.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 10 C4' -C5' -C6 -C7 6.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 11 C4' -C5' -C6 -C11 14.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 12 C4' -C5' -C6 -C5 -28.00 14.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 13 C4 -C5 -C6 -C7 12.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 14 C4 -C5 -C6 -C5' 1.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 15 C4 -C5 -C6 -C11 7.00 0.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 40 C8 -C9 -C12 -C13 -33.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 41 C10 -C9 -C12 -C13 145.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 42 C9 -C12 -C13 -SI2 -14.00 6.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 43 C14 -SI2 -C13 -C12 38.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 44 C16 -SI2 -C13 -C12 -83.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 (CIF) Linear Torsion Angle # 45 C15 -SI2 -C13 -C12 157.00 3.00 1.555 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
18 Alert Level C = Please check
Data collection: COLLECT (Nonius, 1997); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C16H20N2SSi2 | F(000) = 696 |
Mr = 328.58 | Dx = 1.159 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 17.623 (3) Å | Cell parameters from 9092 reflections |
b = 5.7385 (6) Å | θ = 2.9–25.0° |
c = 20.089 (4) Å | µ = 0.30 mm−1 |
β = 112.061 (2)° | T = 170 K |
V = 1882.9 (5) Å3 | Plate, pale yellow |
Z = 4 | 0.23 × 0.18 × 0.09 mm |
Nonius KappaCCD diffractometer | Rint = 0.026 |
116 1.9° images scans | θmax = 25.1°, θmin = 3.7° |
5933 measured reflections | h = −20→20 |
3293 independent reflections | k = −5→6 |
2565 reflections with I > 2σ(I) | l = −23→22 |
Refinement on F2 | 153 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.045 | w = 1/[σ2(Fo2) + (0.0503P)2 + 0.8463P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.116 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.22 e Å−3 |
3293 reflections | Δρmin = −0.31 e Å−3 |
243 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.44860 (4) | 0.29224 (11) | 0.05107 (3) | 0.0503 (2) | |
N1 | 0.44050 (11) | 0.2923 (3) | −0.03182 (9) | 0.0428 (4) | |
N2 | 0.39124 (11) | 0.0737 (3) | 0.05176 (10) | 0.0447 (5) | |
Si2 | 0.18511 (4) | −0.59538 (11) | 0.08332 (3) | 0.0467 (2) | |
Si1 | 0.43559 (8) | 0.4803 (2) | −0.29240 (6) | 0.0449 (3) | 0.6 |
C1 | 0.5337 (4) | 0.6211 (17) | −0.2390 (4) | 0.114 (4) | 0.6 |
H1A | 0.5239 | 0.7489 | −0.2109 | 0.171* | 0.6 |
H1B | 0.559 | 0.6829 | −0.2713 | 0.171* | 0.6 |
H1C | 0.5704 | 0.5065 | −0.2065 | 0.171* | 0.6 |
C2 | 0.3562 (3) | 0.6993 (6) | −0.3370 (2) | 0.0504 (10) | 0.6 |
H2A | 0.3029 | 0.622 | −0.3587 | 0.076* | 0.6 |
H2B | 0.3695 | 0.7787 | −0.3744 | 0.076* | 0.6 |
H2C | 0.3539 | 0.8135 | −0.3015 | 0.076* | 0.6 |
C3 | 0.44912 (19) | 0.2761 (5) | −0.36059 (16) | 0.0712 (8) | 0.6 |
H3A | 0.49 | 0.1575 | −0.3359 | 0.107* | 0.6 |
H3B | 0.4675 | 0.3644 | −0.3935 | 0.107* | 0.6 |
H3C | 0.3968 | 0.2002 | −0.3878 | 0.107* | 0.6 |
C4 | 0.4032 (4) | 0.3100 (13) | −0.2306 (5) | 0.0431 (16) | 0.6 |
C5 | 0.3837 (7) | 0.192 (3) | −0.1890 (9) | 0.037 (2) | 0.6 |
Si1' | 0.48653 (14) | 0.3881 (3) | −0.26928 (11) | 0.0530 (5) | 0.4 |
C1' | 0.4755 (12) | 0.7007 (18) | −0.2668 (9) | 0.165 (7) | 0.4 |
H1D | 0.4921 | 0.7522 | −0.2168 | 0.248* | 0.4 |
H1E | 0.4181 | 0.7435 | −0.2934 | 0.248* | 0.4 |
H1F | 0.5101 | 0.7761 | −0.2888 | 0.248* | 0.4 |
C2' | 0.5949 (4) | 0.3016 (17) | −0.2229 (4) | 0.088 (3) | 0.4 |
H2D | 0.6274 | 0.3628 | −0.2493 | 0.131* | 0.4 |
H2E | 0.5989 | 0.1312 | −0.2208 | 0.131* | 0.4 |
H2F | 0.6158 | 0.3649 | −0.174 | 0.131* | 0.4 |
C3' | 0.44912 (19) | 0.2761 (5) | −0.36059 (16) | 0.0712 (8) | 0.4 |
H3D | 0.3922 | 0.3254 | −0.3858 | 0.107* | 0.4 |
H3E | 0.4519 | 0.1055 | −0.3594 | 0.107* | 0.4 |
H3F | 0.483 | 0.337 | −0.3857 | 0.107* | 0.4 |
C4' | 0.4291 (7) | 0.2492 (17) | −0.2191 (7) | 0.044 (2) | 0.4 |
C5' | 0.4048 (11) | 0.157 (5) | −0.1790 (14) | 0.040 (3) | 0.4 |
C6 | 0.36533 (14) | 0.0481 (4) | −0.13710 (12) | 0.0453 (5) | |
C7 | 0.31601 (16) | −0.1439 (5) | −0.15841 (13) | 0.0607 (7) | |
H7 | 0.2996 | −0.1948 | −0.2068 | 0.073* | |
C8 | 0.28854 (17) | −0.2695 (4) | −0.11123 (14) | 0.0612 (7) | |
H8 | 0.2549 | −0.4025 | −0.129 | 0.073* | |
C9 | 0.30866 (14) | −0.2066 (4) | −0.04080 (12) | 0.0459 (5) | |
C10 | 0.36203 (12) | −0.0114 (4) | −0.01546 (11) | 0.0381 (5) | |
C11 | 0.39001 (12) | 0.1142 (4) | −0.06346 (11) | 0.0376 (5) | |
C12 | 0.27554 (14) | −0.3305 (4) | 0.00449 (12) | 0.0476 (6) | |
C13 | 0.24292 (15) | −0.4364 (4) | 0.03809 (13) | 0.0503 (6) | |
C14 | 0.1070 (2) | −0.7701 (6) | 0.01510 (15) | 0.0827 (10) | |
H14A | 0.0736 | −0.6687 | −0.0242 | 0.124* | |
H14B | 0.072 | −0.8461 | 0.0367 | 0.124* | |
H14C | 0.1337 | −0.8889 | −0.0036 | 0.124* | |
C15 | 0.25396 (19) | −0.7917 (6) | 0.15268 (17) | 0.0897 (11) | |
H15A | 0.2786 | −0.9043 | 0.1301 | 0.135* | |
H15B | 0.2226 | −0.8749 | 0.1764 | 0.135* | |
H15C | 0.2972 | −0.6999 | 0.1883 | 0.135* | |
C16 | 0.1387 (3) | −0.3816 (6) | 0.1249 (2) | 0.1056 (13) | |
H16A | 0.1815 | −0.2803 | 0.1572 | 0.158* | |
H16B | 0.1111 | −0.4636 | 0.1523 | 0.158* | |
H16C | 0.0987 | −0.2871 | 0.0874 | 0.158* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0502 (4) | 0.0626 (4) | 0.0387 (3) | −0.0102 (3) | 0.0175 (3) | −0.0031 (3) |
N1 | 0.0407 (10) | 0.0507 (11) | 0.0395 (10) | −0.0050 (8) | 0.0178 (8) | 0.0026 (8) |
N2 | 0.0443 (10) | 0.0540 (11) | 0.0393 (11) | 0.0015 (9) | 0.0196 (9) | 0.0058 (9) |
Si2 | 0.0546 (4) | 0.0489 (4) | 0.0423 (4) | −0.0157 (3) | 0.0248 (3) | 0.0006 (3) |
Si1 | 0.0462 (7) | 0.0526 (7) | 0.0425 (7) | −0.0010 (6) | 0.0243 (5) | 0.0128 (5) |
C1 | 0.076 (4) | 0.186 (9) | 0.070 (4) | −0.075 (5) | 0.016 (3) | 0.030 (5) |
C2 | 0.076 (3) | 0.036 (2) | 0.049 (2) | −0.0022 (19) | 0.035 (2) | 0.0023 (17) |
C3 | 0.087 (2) | 0.0801 (19) | 0.0645 (18) | 0.0181 (16) | 0.0492 (17) | 0.0221 (15) |
C4 | 0.045 (4) | 0.045 (4) | 0.040 (4) | 0.001 (3) | 0.018 (3) | 0.008 (3) |
C5 | 0.027 (5) | 0.050 (5) | 0.031 (5) | −0.005 (4) | 0.009 (4) | 0.005 (3) |
Si1' | 0.0751 (14) | 0.0474 (10) | 0.0527 (11) | −0.0081 (10) | 0.0425 (11) | 0.0039 (8) |
C1' | 0.32 (2) | 0.060 (6) | 0.231 (17) | −0.006 (10) | 0.239 (17) | 0.007 (8) |
C2' | 0.062 (4) | 0.134 (7) | 0.068 (5) | −0.035 (5) | 0.026 (4) | −0.005 (5) |
C3' | 0.087 (2) | 0.0801 (19) | 0.0645 (18) | 0.0181 (16) | 0.0492 (17) | 0.0221 (15) |
C4' | 0.050 (7) | 0.047 (6) | 0.034 (5) | −0.001 (4) | 0.016 (5) | 0.009 (4) |
C5' | 0.033 (8) | 0.057 (7) | 0.025 (6) | 0.002 (6) | 0.005 (6) | 0.006 (5) |
C6 | 0.0494 (13) | 0.0521 (13) | 0.0393 (12) | −0.0099 (10) | 0.0221 (11) | 0.0020 (10) |
C7 | 0.0779 (18) | 0.0709 (17) | 0.0401 (13) | −0.0301 (14) | 0.0298 (13) | −0.0092 (12) |
C8 | 0.0786 (18) | 0.0581 (16) | 0.0545 (16) | −0.0305 (13) | 0.0337 (14) | −0.0064 (12) |
C9 | 0.0509 (13) | 0.0468 (13) | 0.0458 (13) | −0.0049 (10) | 0.0249 (11) | 0.0075 (10) |
C10 | 0.0372 (11) | 0.0443 (12) | 0.0365 (12) | 0.0047 (9) | 0.0180 (9) | 0.0063 (9) |
C11 | 0.0361 (11) | 0.0425 (12) | 0.0375 (12) | −0.0012 (9) | 0.0175 (9) | 0.0051 (9) |
C12 | 0.0513 (13) | 0.0488 (13) | 0.0461 (13) | −0.0056 (11) | 0.0223 (11) | 0.0064 (11) |
C13 | 0.0558 (14) | 0.0509 (14) | 0.0476 (14) | −0.0070 (11) | 0.0234 (12) | 0.0049 (11) |
C14 | 0.090 (2) | 0.100 (2) | 0.0531 (17) | −0.0446 (18) | 0.0208 (16) | −0.0035 (16) |
C15 | 0.074 (2) | 0.114 (3) | 0.072 (2) | −0.0226 (19) | 0.0173 (17) | 0.0400 (19) |
C16 | 0.153 (3) | 0.065 (2) | 0.156 (4) | −0.025 (2) | 0.124 (3) | −0.016 (2) |
S1—N2 | 1.6141 (19) | C1'—H1E | 0.9800 |
S1—N1 | 1.6169 (19) | C1'—H1F | 0.9800 |
N1—C11 | 1.348 (3) | C2'—H2D | 0.9800 |
N2—C10 | 1.344 (3) | C2'—H2E | 0.9800 |
Si2—C14 | 1.833 (3) | C2'—H2F | 0.9800 |
Si2—C16 | 1.840 (3) | C4'—C5' | 1.17 (3) |
Si2—C13 | 1.842 (2) | C5'—C6 | 1.42 (3) |
Si2—C15 | 1.847 (3) | C6—C7 | 1.369 (3) |
Si1—C4 | 1.832 (10) | C6—C11 | 1.428 (3) |
Si1—C2 | 1.843 (4) | C7—C8 | 1.413 (3) |
Si1—C1 | 1.844 (6) | C7—H7 | 0.9500 |
Si1—C3 | 1.885 (3) | C8—C9 | 1.371 (3) |
C1—H1A | 0.9800 | C8—H8 | 0.9500 |
C1—H1B | 0.9800 | C9—C10 | 1.428 (3) |
C1—H1C | 0.9800 | C9—C12 | 1.440 (3) |
C2—H2A | 0.9800 | C10—C11 | 1.432 (3) |
C2—H2B | 0.9800 | C12—C13 | 1.203 (3) |
C2—H2C | 0.9800 | C14—H14A | 0.9800 |
C3—H3A | 0.9800 | C14—H14B | 0.9800 |
C3—H3B | 0.9800 | C14—H14C | 0.9800 |
C3—H3C | 0.9800 | C15—H15A | 0.9800 |
C4—C5 | 1.219 (19) | C15—H15B | 0.9800 |
C5—C6 | 1.460 (18) | C15—H15C | 0.9800 |
Si1'—C1' | 1.808 (11) | C16—H16A | 0.9800 |
Si1'—C2' | 1.851 (8) | C16—H16B | 0.9800 |
Si1'—C4' | 1.855 (14) | C16—H16C | 0.9800 |
C1'—H1D | 0.9800 | ||
N2—S1—N1 | 101.28 (9) | C7—C6—C5 | 121.2 (7) |
C11—N1—S1 | 105.85 (14) | C11—C6—C5 | 121.8 (7) |
C10—N2—S1 | 106.18 (14) | C6—C7—C8 | 122.6 (2) |
C14—Si2—C16 | 111.54 (18) | C6—C7—H7 | 118.7 |
C14—Si2—C13 | 107.53 (12) | C8—C7—H7 | 118.7 |
C16—Si2—C13 | 108.45 (12) | C9—C8—C7 | 122.5 (2) |
C14—Si2—C15 | 109.06 (16) | C9—C8—H8 | 118.8 |
C16—Si2—C15 | 110.00 (19) | C7—C8—H8 | 118.8 |
C13—Si2—C15 | 110.24 (13) | C8—C9—C10 | 117.03 (19) |
C4—Si1—C2 | 108.7 (2) | C8—C9—C12 | 120.9 (2) |
C4—Si1—C1 | 107.6 (3) | C10—C9—C12 | 122.1 (2) |
C2—Si1—C1 | 111.0 (3) | N2—C10—C9 | 126.57 (19) |
C4—Si1—C3 | 108.5 (3) | N2—C10—C11 | 113.28 (19) |
C2—Si1—C3 | 110.53 (16) | C9—C10—C11 | 120.15 (19) |
C1—Si1—C3 | 110.4 (3) | N1—C11—C6 | 125.49 (18) |
C5—C4—Si1 | 178.0 (7) | N1—C11—C10 | 113.42 (19) |
C4—C5—C6 | 176.7 (9) | C6—C11—C10 | 121.09 (19) |
C1'—Si1'—C2' | 110.7 (7) | C13—C12—C9 | 175.4 (3) |
C1'—Si1'—C4' | 109.0 (5) | C12—C13—Si2 | 175.4 (2) |
C2'—Si1'—C4' | 106.4 (4) | Si2—C14—H14A | 109.5 |
Si1'—C1'—H1D | 109.5 | Si2—C14—H14B | 109.5 |
Si1'—C1'—H1E | 109.5 | H14A—C14—H14B | 109.5 |
H1D—C1'—H1E | 109.5 | Si2—C14—H14C | 109.5 |
Si1'—C1'—H1F | 109.5 | H14A—C14—H14C | 109.5 |
H1D—C1'—H1F | 109.5 | H14B—C14—H14C | 109.5 |
H1E—C1'—H1F | 109.5 | Si2—C15—H15A | 109.5 |
Si1'—C2'—H2D | 109.5 | Si2—C15—H15B | 109.5 |
Si1'—C2'—H2E | 109.5 | H15A—C15—H15B | 109.5 |
H2D—C2'—H2E | 109.5 | Si2—C15—H15C | 109.5 |
Si1'—C2'—H2F | 109.5 | H15A—C15—H15C | 109.5 |
H2D—C2'—H2F | 109.5 | H15B—C15—H15C | 109.5 |
H2E—C2'—H2F | 109.5 | Si2—C16—H16A | 109.5 |
C5'—C4'—Si1' | 169.4 (12) | Si2—C16—H16B | 109.5 |
C4'—C5'—C6 | 172.8 (16) | H16A—C16—H16B | 109.5 |
C7—C6—C5' | 124.3 (12) | Si2—C16—H16C | 109.5 |
C7—C6—C11 | 116.6 (2) | H16A—C16—H16C | 109.5 |
C5'—C6—C11 | 118.0 (11) | H16B—C16—H16C | 109.5 |
N2—S1—N1—C11 | 0.35 (16) | C8—C9—C10—N2 | −177.7 (2) |
N1—S1—N2—C10 | −0.16 (16) | C12—C9—C10—N2 | 3.6 (3) |
C2—Si1—C4—C5 | 18E1 (10) | C8—C9—C10—C11 | 2.0 (3) |
C1—Si1—C4—C5 | −7E1 (3) | C12—C9—C10—C11 | −176.7 (2) |
C3—Si1—C4—C5 | 5E1 (3) | S1—N1—C11—C6 | −179.93 (19) |
Si1—C4—C5—C6 | 3E1 (6) | S1—N1—C11—C10 | −0.4 (2) |
C1'—Si1'—C4'—C5' | −103 (9) | C7—C6—C11—N1 | 177.6 (2) |
C2'—Si1'—C4'—C5' | 17 (9) | C5'—C6—C11—N1 | 8.8 (9) |
Si1'—C4'—C5'—C6 | −179 (12) | C5—C6—C11—N1 | −9.2 (6) |
C4'—C5'—C6—C7 | 6E1 (2) | C7—C6—C11—C10 | −1.9 (3) |
C4'—C5'—C6—C11 | −14E1 (2) | C5'—C6—C11—C10 | −170.7 (8) |
C4'—C5'—C6—C5 | −28 (14) | C5—C6—C11—C10 | 171.3 (5) |
C4—C5—C6—C7 | −12E1 (3) | N2—C10—C11—N1 | 0.4 (3) |
C4—C5—C6—C5' | −1E1 (2) | C9—C10—C11—N1 | −179.41 (19) |
C4—C5—C6—C11 | 7E1 (3) | N2—C10—C11—C6 | 179.88 (19) |
C5'—C6—C7—C8 | 169.6 (8) | C9—C10—C11—C6 | 0.1 (3) |
C11—C6—C7—C8 | 1.5 (4) | C8—C9—C12—C13 | −33 (3) |
C5—C6—C7—C8 | −171.7 (6) | C10—C9—C12—C13 | 145 (3) |
C6—C7—C8—C9 | 0.7 (5) | C9—C12—C13—Si2 | −14 (6) |
C7—C8—C9—C10 | −2.5 (4) | C14—Si2—C13—C12 | 38 (3) |
C7—C8—C9—C12 | 176.3 (3) | C16—Si2—C13—C12 | −83 (3) |
S1—N2—C10—C9 | 179.67 (18) | C15—Si2—C13—C12 | 157 (3) |
S1—N2—C10—C11 | −0.1 (2) |
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