Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807011191/sg2146sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807011191/sg2146Isup2.hkl |
CCDC reference: 643091
Key indicators
- Single-crystal X-ray study
- T = 120 K
- Mean (Wave) = 0.000 Å
- R factor = 0.055
- wR factor = 0.173
- Data-to-parameter ratio = 17.4
checkCIF/PLATON results
No syntax errors found
Alert level C REFLT03_ALERT_3_C Reflection count < 95% complete From the CIF: _diffrn_reflns_theta_max 26.99 From the CIF: _diffrn_reflns_theta_full 25.00 From the CIF: _reflns_number_total 4423 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4660 Completeness (_total/calc) 94.91%
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe & Cie, ????); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.
C20H19NO2P2S3 | F(000) = 960 |
Mr = 463.48 | Dx = 1.443 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 7382 reflections |
a = 10.406 (2) Å | θ = 4.0–54.1° |
b = 15.8954 (17) Å | µ = 0.51 mm−1 |
c = 13.0056 (18) Å | T = 120 K |
β = 97.326 (13)° | Block, colourless |
V = 2133.8 (6) Å3 | 0.50 × 0.40 × 0.40 mm |
Z = 4 |
Stoe IPDSII diffractometer | 2411 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.079 |
Graphite monochromator | θmax = 27.0°, θmin = 2.0° |
Detector resolution: 6.67 pixels mm-1 | h = −13→9 |
rotation scans | k = −20→19 |
7973 measured reflections | l = −14→16 |
4423 independent reflections |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.173 | H-atom parameters constrained |
S = 0.90 | w = 1/[σ2(Fo2) + (0.0967P)2] where P = (Fo2 + 2Fc2)/3 |
4423 reflections | (Δ/σ)max < 0.001 |
254 parameters | Δρmax = 0.61 e Å−3 |
0 restraints | Δρmin = −0.77 e Å−3 |
Experimental. The synthesis was performed in an atmosphere of purified dinitrogen. |
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 | 0.7048 (4) | 0.1926 (2) | 0.9498 (3) | 0.0325 (9) | |
P1 | 0.84046 (13) | 0.13897 (7) | 0.93200 (10) | 0.0318 (3) | |
P2 | 0.58815 (12) | 0.12013 (7) | 0.95707 (10) | 0.0304 (3) | |
S1 | 0.92251 (13) | 0.17414 (9) | 0.81448 (10) | 0.0415 (3) | |
S2 | 0.72583 (13) | 0.02863 (7) | 0.92328 (10) | 0.0346 (3) | |
S3 | 0.51615 (13) | 0.11208 (7) | 1.08651 (10) | 0.0364 (3) | |
O1 | 1.1882 (4) | 0.1211 (2) | 1.3307 (3) | 0.0452 (9) | |
O2 | 0.2142 (3) | 0.1499 (2) | 0.5740 (3) | 0.0381 (8) | |
C1 | 0.9482 (5) | 0.1346 (3) | 1.0513 (3) | 0.0297 (9) | |
C2 | 0.9014 (5) | 0.1076 (3) | 1.1431 (4) | 0.0414 (12) | |
H2A | 0.8132 | 0.0916 | 1.1420 | 0.050* | |
C3 | 0.9853 (5) | 0.1048 (3) | 1.2347 (4) | 0.0443 (13) | |
H3A | 0.9547 | 0.0868 | 1.2969 | 0.053* | |
C4 | 1.1145 (5) | 0.1283 (3) | 1.2359 (4) | 0.0370 (11) | |
C5 | 1.1599 (5) | 0.1553 (3) | 1.1473 (4) | 0.0338 (10) | |
H5A | 1.2478 | 0.1720 | 1.1488 | 0.041* | |
C6 | 1.0757 (5) | 0.1582 (3) | 1.0546 (4) | 0.0345 (11) | |
H6A | 1.1070 | 0.1768 | 0.9930 | 0.041* | |
C7 | 1.3238 (5) | 0.1418 (3) | 1.3347 (5) | 0.0446 (13) | |
H7A | 1.3668 | 0.1345 | 1.4057 | 0.067* | |
H7B | 1.3327 | 0.2004 | 1.3132 | 0.067* | |
H7C | 1.3641 | 0.1046 | 1.2879 | 0.067* | |
C8 | 0.4709 (4) | 0.1299 (3) | 0.8443 (3) | 0.0283 (9) | |
C9 | 0.3401 (5) | 0.1145 (3) | 0.8485 (4) | 0.0346 (10) | |
H9A | 0.3116 | 0.1003 | 0.9128 | 0.041* | |
C10 | 0.2500 (5) | 0.1198 (3) | 0.7592 (4) | 0.0351 (11) | |
H10A | 0.1609 | 0.1085 | 0.7623 | 0.042* | |
C11 | 0.2926 (5) | 0.1419 (3) | 0.6662 (4) | 0.0340 (10) | |
C12 | 0.4235 (5) | 0.1576 (3) | 0.6598 (4) | 0.0344 (11) | |
H12A | 0.4514 | 0.1729 | 0.5956 | 0.041* | |
C13 | 0.5125 (5) | 0.1505 (3) | 0.7490 (4) | 0.0332 (10) | |
H13A | 0.6020 | 0.1597 | 0.7453 | 0.040* | |
C14 | 0.0796 (5) | 0.1280 (3) | 0.5717 (4) | 0.0432 (12) | |
H14A | 0.0339 | 0.1389 | 0.5023 | 0.065* | |
H14B | 0.0411 | 0.1621 | 0.6227 | 0.065* | |
H14C | 0.0722 | 0.0683 | 0.5885 | 0.065* | |
C15 | 0.6980 (5) | 0.2825 (3) | 0.9617 (4) | 0.0306 (10) | |
C16 | 0.7338 (5) | 0.3185 (3) | 1.0580 (4) | 0.0346 (11) | |
H16A | 0.7584 | 0.2839 | 1.1168 | 0.041* | |
C17 | 0.7335 (6) | 0.4053 (3) | 1.0682 (4) | 0.0410 (12) | |
H17A | 0.7594 | 0.4302 | 1.1339 | 0.049* | |
C18 | 0.6957 (6) | 0.4556 (3) | 0.9832 (4) | 0.0438 (13) | |
H18A | 0.6943 | 0.5150 | 0.9909 | 0.053* | |
C19 | 0.6599 (6) | 0.4196 (3) | 0.8870 (4) | 0.0427 (13) | |
H19A | 0.6345 | 0.4543 | 0.8284 | 0.051* | |
C20 | 0.6612 (5) | 0.3327 (3) | 0.8760 (4) | 0.0399 (12) | |
H20A | 0.6369 | 0.3078 | 0.8100 | 0.048* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.041 (2) | 0.0306 (19) | 0.026 (2) | −0.0033 (16) | 0.0041 (17) | 0.0006 (15) |
P1 | 0.0356 (7) | 0.0332 (6) | 0.0277 (6) | 0.0006 (5) | 0.0085 (5) | 0.0001 (5) |
P2 | 0.0358 (6) | 0.0289 (5) | 0.0276 (6) | 0.0004 (5) | 0.0083 (5) | −0.0011 (4) |
S1 | 0.0410 (7) | 0.0552 (7) | 0.0301 (7) | 0.0016 (6) | 0.0120 (5) | 0.0045 (5) |
S2 | 0.0405 (7) | 0.0293 (5) | 0.0347 (7) | 0.0027 (5) | 0.0078 (5) | −0.0028 (5) |
S3 | 0.0431 (7) | 0.0385 (6) | 0.0291 (6) | −0.0038 (5) | 0.0106 (5) | 0.0001 (5) |
O1 | 0.047 (2) | 0.057 (2) | 0.032 (2) | −0.0109 (17) | 0.0020 (16) | 0.0053 (16) |
O2 | 0.041 (2) | 0.0426 (18) | 0.0305 (19) | 0.0028 (15) | 0.0041 (16) | −0.0018 (14) |
C1 | 0.034 (2) | 0.032 (2) | 0.023 (2) | −0.0006 (18) | 0.0062 (19) | −0.0007 (17) |
C2 | 0.041 (3) | 0.048 (3) | 0.036 (3) | −0.005 (2) | 0.009 (2) | 0.002 (2) |
C3 | 0.047 (3) | 0.054 (3) | 0.033 (3) | −0.011 (2) | 0.010 (2) | 0.004 (2) |
C4 | 0.046 (3) | 0.034 (2) | 0.032 (3) | −0.001 (2) | 0.005 (2) | 0.0047 (19) |
C5 | 0.034 (3) | 0.034 (2) | 0.034 (3) | −0.0020 (19) | 0.008 (2) | 0.0006 (19) |
C6 | 0.040 (3) | 0.030 (2) | 0.034 (3) | −0.0019 (19) | 0.007 (2) | 0.0015 (18) |
C7 | 0.035 (3) | 0.052 (3) | 0.046 (3) | −0.011 (2) | 0.003 (2) | 0.009 (2) |
C8 | 0.033 (2) | 0.028 (2) | 0.025 (2) | 0.0013 (17) | 0.0085 (18) | −0.0013 (17) |
C9 | 0.041 (3) | 0.035 (2) | 0.030 (3) | 0.000 (2) | 0.012 (2) | 0.0033 (19) |
C10 | 0.038 (3) | 0.035 (2) | 0.033 (3) | −0.002 (2) | 0.008 (2) | 0.0027 (19) |
C11 | 0.044 (3) | 0.030 (2) | 0.029 (3) | −0.001 (2) | 0.008 (2) | −0.0015 (18) |
C12 | 0.044 (3) | 0.033 (2) | 0.028 (3) | −0.0035 (19) | 0.010 (2) | 0.0018 (18) |
C13 | 0.034 (3) | 0.034 (2) | 0.033 (3) | −0.0012 (19) | 0.009 (2) | −0.0036 (18) |
C14 | 0.038 (3) | 0.054 (3) | 0.037 (3) | −0.003 (2) | 0.003 (2) | −0.001 (2) |
C15 | 0.038 (3) | 0.024 (2) | 0.031 (2) | 0.0008 (18) | 0.010 (2) | −0.0015 (17) |
C16 | 0.045 (3) | 0.032 (2) | 0.029 (3) | 0.002 (2) | 0.012 (2) | 0.0022 (18) |
C17 | 0.056 (3) | 0.033 (2) | 0.035 (3) | −0.001 (2) | 0.010 (2) | −0.006 (2) |
C18 | 0.060 (4) | 0.025 (2) | 0.049 (3) | −0.001 (2) | 0.015 (3) | 0.002 (2) |
C19 | 0.053 (3) | 0.034 (2) | 0.041 (3) | 0.002 (2) | 0.004 (3) | 0.005 (2) |
C20 | 0.053 (3) | 0.030 (2) | 0.038 (3) | −0.001 (2) | 0.007 (2) | 0.000 (2) |
N1—C15 | 1.441 (5) | C7—H7C | 0.9800 |
N1—P1 | 1.690 (4) | C8—C9 | 1.391 (7) |
N1—P2 | 1.684 (4) | C8—C13 | 1.402 (6) |
P1—S1 | 1.9263 (19) | C9—C10 | 1.400 (7) |
P1—S2 | 2.1160 (17) | C9—H9A | 0.9500 |
P2—S2 | 2.1265 (17) | C10—C11 | 1.385 (7) |
P2—S3 | 1.9322 (19) | C10—H10A | 0.9500 |
P1—C1 | 1.796 (4) | C11—C12 | 1.398 (7) |
P2—C8 | 1.791 (5) | C12—C13 | 1.394 (7) |
O1—C4 | 1.371 (6) | C12—H12A | 0.9500 |
O1—C7 | 1.444 (6) | C13—H13A | 0.9500 |
O2—C11 | 1.368 (6) | C14—H14A | 0.9800 |
O2—C14 | 1.440 (6) | C14—H14B | 0.9800 |
C1—C6 | 1.374 (7) | C14—H14C | 0.9800 |
C1—C2 | 1.414 (7) | C15—C20 | 1.384 (7) |
C2—C3 | 1.385 (7) | C15—C16 | 1.384 (7) |
C2—H2A | 0.9500 | C16—C17 | 1.386 (6) |
C3—C4 | 1.394 (8) | C16—H16A | 0.9500 |
C3—H3A | 0.9500 | C17—C18 | 1.380 (7) |
C4—C5 | 1.369 (7) | C17—H17A | 0.9500 |
C5—C6 | 1.398 (7) | C18—C19 | 1.383 (8) |
C5—H5A | 0.9500 | C18—H18A | 0.9500 |
C6—H6A | 0.9500 | C19—C20 | 1.389 (7) |
C7—H7A | 0.9800 | C19—H19A | 0.9500 |
C7—H7B | 0.9800 | C20—H20A | 0.9500 |
P1—N1—P2 | 106.5 (2) | C9—C8—C13 | 119.3 (4) |
P1—S2—P2 | 79.17 (6) | C9—C8—P2 | 121.4 (4) |
N1—P1—S1 | 115.15 (15) | C13—C8—P2 | 119.3 (4) |
N1—P1—S2 | 87.14 (14) | C8—C9—C10 | 120.9 (5) |
N1—P2—S2 | 86.93 (15) | C8—C9—H9A | 119.6 |
N1—P2—S3 | 117.17 (15) | C10—C9—H9A | 119.6 |
S1—P1—S2 | 120.13 (8) | C11—C10—C9 | 119.0 (5) |
S2—P2—S3 | 118.76 (8) | C11—C10—H10A | 120.5 |
C15—N1—P2 | 128.8 (3) | C9—C10—H10A | 120.5 |
C15—N1—P1 | 124.6 (3) | O2—C11—C10 | 124.6 (5) |
N1—P1—C1 | 110.0 (2) | O2—C11—C12 | 114.1 (4) |
C1—P1—S1 | 113.91 (17) | C10—C11—C12 | 121.3 (4) |
C1—P1—S2 | 107.47 (15) | C13—C12—C11 | 119.0 (5) |
N1—P2—C8 | 108.4 (2) | C13—C12—H12A | 120.5 |
C8—P2—S3 | 114.83 (17) | C11—C12—H12A | 120.5 |
C8—P2—S2 | 107.27 (16) | C12—C13—C8 | 120.5 (5) |
C4—O1—C7 | 116.5 (4) | C12—C13—H13A | 119.8 |
C11—O2—C14 | 117.7 (4) | C8—C13—H13A | 119.8 |
C6—C1—C2 | 119.5 (4) | O2—C14—H14A | 109.5 |
C6—C1—P1 | 120.7 (4) | O2—C14—H14B | 109.5 |
C2—C1—P1 | 119.8 (4) | H14A—C14—H14B | 109.5 |
C3—C2—C1 | 119.3 (5) | O2—C14—H14C | 109.5 |
C3—C2—H2A | 120.3 | H14A—C14—H14C | 109.5 |
C1—C2—H2A | 120.3 | H14B—C14—H14C | 109.5 |
C2—C3—C4 | 120.1 (5) | C20—C15—C16 | 120.4 (4) |
C2—C3—H3A | 119.9 | C20—C15—N1 | 119.9 (4) |
C4—C3—H3A | 119.9 | C16—C15—N1 | 119.7 (4) |
C5—C4—O1 | 124.7 (5) | C15—C16—C17 | 119.5 (4) |
C5—C4—C3 | 120.7 (5) | C15—C16—H16A | 120.2 |
O1—C4—C3 | 114.5 (5) | C17—C16—H16A | 120.2 |
C4—C5—C6 | 119.4 (5) | C18—C17—C16 | 120.3 (5) |
C4—C5—H5A | 120.3 | C18—C17—H17A | 119.8 |
C6—C5—H5A | 120.3 | C16—C17—H17A | 119.8 |
C1—C6—C5 | 121.0 (5) | C17—C18—C19 | 120.1 (4) |
C1—C6—H6A | 119.5 | C17—C18—H18A | 119.9 |
C5—C6—H6A | 119.5 | C19—C18—H18A | 119.9 |
O1—C7—H7A | 109.5 | C18—C19—C20 | 119.9 (5) |
O1—C7—H7B | 109.5 | C18—C19—H19A | 120.1 |
H7A—C7—H7B | 109.5 | C20—C19—H19A | 120.1 |
O1—C7—H7C | 109.5 | C15—C20—C19 | 119.8 (5) |
H7A—C7—H7C | 109.5 | C15—C20—H20A | 120.1 |
H7B—C7—H7C | 109.5 | C19—C20—H20A | 120.1 |
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