Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019729/cv6077sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019729/cv6077Isup2.hkl |
CCDC reference: 177225
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989b); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); molecular graphics: ORTEX (McArdle, 1995) and PLUTON92 (Spek, 1992); software used to prepare material for publication: PARST97 (Nardelli, 1996).
C21H21N2O3PS | Z = 2 |
Mr = 412.43 | F(000) = 432 |
Triclinic, P1 | Dx = 1.300 Mg m−3 Dm = 1.294 Mg m−3 Dm measured by flotation in xylene, bromobenzene, heptane & toluene |
a = 9.753 (1) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 10.069 (1) Å | Cell parameters from 25 reflections |
c = 12.255 (1) Å | θ = 22.5–30.4° |
α = 98.17 (1)° | µ = 2.28 mm−1 |
β = 103.37 (1)° | T = 293 K |
γ = 111.63 (1)° | Prism, colourless |
V = 1053.5 (2) Å3 | 0.5 × 0.3 × 0.3 mm |
Rigaku AFC-5S diffractometer | 2609 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.014 |
Graphite monochromator | θmax = 72.6°, θmin = 3.8° |
ω scans | h = −12→11 |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | k = 0→12 |
Tmin = 0.356, Tmax = 0.619 | l = −15→15 |
4248 measured reflections | 3 standard reflections every 150 reflections |
3996 independent reflections | intensity decay: <2% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.051 | w = 1/[σ2(Fo2) + (0.0837P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.130 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.37 e Å−3 |
3995 reflections | Δρmin = −0.51 e Å−3 |
267 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0125 (10) |
Primary atom site location: structure-invariant direct methods |
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 on F2 for ALL reflections except for 1 with very negative F2 or flagged by the user for potential systematic errors. 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-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 | ||
S1 | 0.37994 (8) | 0.06954 (7) | 0.19273 (6) | 0.0646 (2) | |
C1 | 0.4535 (3) | 0.2475 (3) | 0.2626 (2) | 0.0514 (6) | |
N1 | 0.5642 (3) | 0.3582 (3) | 0.2393 (2) | 0.0616 (6) | |
H1 | 0.574 (3) | 0.447 (3) | 0.274 (2) | 0.069 (8)* | |
N2 | 0.4071 (3) | 0.2969 (3) | 0.3492 (2) | 0.0588 (6) | |
H2 | 0.444 (3) | 0.390 (3) | 0.373 (2) | 0.062 (8)* | |
C2 | 0.2823 (3) | 0.2059 (3) | 0.3875 (2) | 0.0575 (6) | |
H201 | 0.262 (3) | 0.099 (3) | 0.345 (2) | 0.058 (7)* | |
C3 | 0.1441 (3) | 0.2447 (4) | 0.3585 (3) | 0.0814 (9) | |
H301 | 0.0645 (11) | 0.1837 (17) | 0.3860 (18) | 0.122* | |
H302 | 0.1048 (16) | 0.228 (2) | 0.2761 (3) | 0.122* | |
H303 | 0.1756 (7) | 0.3466 (7) | 0.3951 (16) | 0.122* | |
P1 | 0.36202 (8) | 0.23343 (7) | 0.54149 (6) | 0.0561 (2) | |
O1 | 0.4222 (2) | 0.3870 (2) | 0.6077 (2) | 0.0660 (5) | |
O2 | 0.2247 (2) | 0.1198 (2) | 0.57135 (14) | 0.0631 (5) | |
O3 | 0.4843 (2) | 0.1648 (2) | 0.5597 (2) | 0.0653 (5) | |
C11 | 0.6430 (3) | 0.3498 (3) | 0.1567 (2) | 0.0555 (6) | |
C12 | 0.7014 (3) | 0.2458 (3) | 0.1408 (2) | 0.0642 (7) | |
H12 | 0.6874 (3) | 0.1756 (3) | 0.1839 (2) | 0.077* | |
C13 | 0.7802 (3) | 0.2454 (3) | 0.0616 (3) | 0.0751 (8) | |
H13 | 0.8179 (3) | 0.1738 (3) | 0.0503 (3) | 0.090* | |
C14 | 0.8040 (4) | 0.3496 (4) | −0.0014 (3) | 0.0841 (10) | |
H14 | 0.8567 (4) | 0.3481 (4) | −0.0555 (3) | 0.101* | |
C15 | 0.7500 (4) | 0.4552 (4) | 0.0158 (3) | 0.0863 (10) | |
H15 | 0.7678 (4) | 0.5271 (4) | −0.0256 (3) | 0.104* | |
C16 | 0.6685 (3) | 0.4563 (3) | 0.0948 (2) | 0.0708 (8) | |
H16 | 0.6313 (3) | 0.5283 (3) | 0.1059 (2) | 0.085* | |
C21 | 0.2160 (3) | 0.1294 (3) | 0.6864 (2) | 0.0566 (6) | |
C22 | 0.0865 (3) | 0.1380 (3) | 0.7057 (2) | 0.0669 (7) | |
H22 | 0.0104 (3) | 0.1418 (3) | 0.6460 (2) | 0.080* | |
C23 | 0.0702 (4) | 0.1411 (4) | 0.8150 (3) | 0.0809 (9) | |
H23 | −0.0166 (4) | 0.1480 (4) | 0.8298 (3) | 0.097* | |
C24 | 0.1840 (4) | 0.1339 (4) | 0.9022 (3) | 0.0825 (9) | |
H24 | 0.1736 (4) | 0.1354 (4) | 0.9758 (3) | 0.099* | |
C25 | 0.3115 (4) | 0.1244 (3) | 0.8804 (3) | 0.0818 (9) | |
H25 | 0.3875 (4) | 0.1201 (3) | 0.9399 (3) | 0.098* | |
C26 | 0.3302 (3) | 0.1212 (3) | 0.7718 (3) | 0.0698 (7) | |
H26 | 0.4167 (3) | 0.1138 (3) | 0.7569 (3) | 0.084* | |
C31 | 0.6437 (3) | 0.2453 (3) | 0.5773 (2) | 0.0596 (6) | |
C32 | 0.7361 (4) | 0.3422 (4) | 0.6820 (3) | 0.0803 (9) | |
H32 | 0.6941 (4) | 0.3573 (4) | 0.7410 (3) | 0.096* | |
C33 | 0.8916 (4) | 0.4164 (4) | 0.6986 (3) | 0.0980 (11) | |
H33 | 0.9560 (4) | 0.4813 (4) | 0.7698 (3) | 0.118* | |
C34 | 0.9525 (4) | 0.3957 (5) | 0.6110 (4) | 0.1060 (13) | |
H34 | 1.0577 (4) | 0.4480 (5) | 0.6220 (4) | 0.127* | |
C35 | 0.8579 (4) | 0.2975 (5) | 0.5071 (4) | 0.0991 (12) | |
H35 | 0.8989 (4) | 0.2832 (5) | 0.4474 (4) | 0.119* | |
C36 | 0.7016 (3) | 0.2196 (4) | 0.4906 (3) | 0.0734 (8) | |
H36 | 0.6375 (3) | 0.1507 (4) | 0.4210 (3) | 0.088* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0710 (4) | 0.0543 (4) | 0.0614 (4) | 0.0187 (3) | 0.0255 (3) | 0.0050 (3) |
C1 | 0.0541 (14) | 0.0540 (14) | 0.0481 (12) | 0.0229 (11) | 0.0192 (11) | 0.0121 (10) |
N1 | 0.0731 (14) | 0.0531 (13) | 0.0630 (13) | 0.0234 (11) | 0.0355 (11) | 0.0117 (10) |
N2 | 0.0683 (14) | 0.0491 (13) | 0.0615 (12) | 0.0196 (11) | 0.0338 (11) | 0.0116 (10) |
C2 | 0.0602 (15) | 0.0553 (15) | 0.0623 (15) | 0.0223 (12) | 0.0296 (12) | 0.0174 (12) |
C3 | 0.072 (2) | 0.098 (2) | 0.092 (2) | 0.043 (2) | 0.034 (2) | 0.036 (2) |
P1 | 0.0602 (4) | 0.0488 (4) | 0.0612 (4) | 0.0188 (3) | 0.0292 (3) | 0.0133 (3) |
O1 | 0.0794 (12) | 0.0465 (10) | 0.0714 (11) | 0.0192 (9) | 0.0378 (10) | 0.0082 (8) |
O2 | 0.0626 (11) | 0.0607 (10) | 0.0605 (10) | 0.0146 (9) | 0.0272 (8) | 0.0165 (8) |
O3 | 0.0588 (10) | 0.0545 (10) | 0.0825 (12) | 0.0224 (8) | 0.0237 (9) | 0.0167 (9) |
C11 | 0.0581 (14) | 0.0539 (14) | 0.0489 (13) | 0.0163 (12) | 0.0208 (11) | 0.0088 (11) |
C12 | 0.071 (2) | 0.061 (2) | 0.0627 (15) | 0.0260 (13) | 0.0276 (13) | 0.0128 (12) |
C13 | 0.075 (2) | 0.075 (2) | 0.074 (2) | 0.026 (2) | 0.035 (2) | 0.0070 (15) |
C14 | 0.092 (2) | 0.092 (2) | 0.068 (2) | 0.027 (2) | 0.046 (2) | 0.011 (2) |
C15 | 0.106 (3) | 0.087 (2) | 0.077 (2) | 0.034 (2) | 0.050 (2) | 0.034 (2) |
C16 | 0.083 (2) | 0.069 (2) | 0.068 (2) | 0.030 (2) | 0.036 (2) | 0.0236 (14) |
C21 | 0.0601 (15) | 0.0523 (14) | 0.0593 (14) | 0.0188 (11) | 0.0261 (12) | 0.0194 (11) |
C22 | 0.064 (2) | 0.071 (2) | 0.070 (2) | 0.0274 (14) | 0.0250 (14) | 0.0261 (14) |
C23 | 0.084 (2) | 0.087 (2) | 0.086 (2) | 0.036 (2) | 0.047 (2) | 0.026 (2) |
C24 | 0.104 (3) | 0.079 (2) | 0.065 (2) | 0.031 (2) | 0.036 (2) | 0.025 (2) |
C25 | 0.091 (2) | 0.078 (2) | 0.068 (2) | 0.029 (2) | 0.015 (2) | 0.029 (2) |
C26 | 0.064 (2) | 0.072 (2) | 0.079 (2) | 0.0282 (14) | 0.0237 (15) | 0.0299 (15) |
C31 | 0.0562 (15) | 0.059 (2) | 0.066 (2) | 0.0238 (12) | 0.0187 (12) | 0.0215 (12) |
C32 | 0.077 (2) | 0.084 (2) | 0.066 (2) | 0.027 (2) | 0.0115 (15) | 0.016 (2) |
C33 | 0.071 (2) | 0.090 (3) | 0.102 (3) | 0.019 (2) | −0.005 (2) | 0.026 (2) |
C34 | 0.059 (2) | 0.111 (3) | 0.148 (4) | 0.033 (2) | 0.015 (2) | 0.068 (3) |
C35 | 0.081 (2) | 0.139 (3) | 0.121 (3) | 0.068 (2) | 0.053 (2) | 0.065 (3) |
C36 | 0.068 (2) | 0.093 (2) | 0.074 (2) | 0.047 (2) | 0.0233 (15) | 0.025 (2) |
S1—C1 | 1.671 (2) | C15—C16 | 1.388 (4) |
C1—N2 | 1.347 (3) | C15—H15 | 0.93 |
C1—N1 | 1.355 (3) | C16—H16 | 0.93 |
N1—C11 | 1.416 (3) | C21—C22 | 1.368 (4) |
N1—H1 | 0.90 (3) | C21—C26 | 1.377 (4) |
N2—C2 | 1.451 (3) | C22—C23 | 1.383 (4) |
N2—H2 | 0.85 (3) | C22—H22 | 0.93 |
C2—C3 | 1.517 (4) | C23—C24 | 1.383 (5) |
C2—P1 | 1.805 (3) | C23—H23 | 0.93 |
C2—H201 | 1.05 (2) | C24—C25 | 1.364 (4) |
C3—H301 | 0.96 | C24—H24 | 0.93 |
C3—H302 | 0.96 | C25—C26 | 1.382 (4) |
C3—H303 | 0.96 | C25—H25 | 0.93 |
P1—O1 | 1.465 (2) | C26—H26 | 0.93 |
P1—O2 | 1.566 (2) | C31—C36 | 1.349 (4) |
P1—O3 | 1.574 (2) | C31—C32 | 1.368 (4) |
O2—C21 | 1.423 (3) | C32—C33 | 1.370 (4) |
O3—C31 | 1.410 (3) | C32—H32 | 0.93 |
C11—C12 | 1.375 (4) | C33—C34 | 1.367 (5) |
C11—C16 | 1.382 (4) | C33—H33 | 0.93 |
C12—C13 | 1.372 (3) | C34—C35 | 1.371 (6) |
C12—H12 | 0.93 | C34—H34 | 0.93 |
C13—C14 | 1.373 (5) | C35—C36 | 1.382 (4) |
C13—H13 | 0.93 | C35—H35 | 0.93 |
C14—C15 | 1.360 (5) | C36—H36 | 0.93 |
C14—H14 | 0.93 | ||
N2—C1—N1 | 112.3 (2) | C14—C15—H15 | 119.8 |
N2—C1—S1 | 123.0 (2) | C16—C15—H15 | 119.8 |
N1—C1—S1 | 124.7 (2) | C11—C16—C15 | 119.6 (3) |
C1—N1—C11 | 128.9 (2) | C11—C16—H16 | 120.2 |
C1—N1—H1 | 111.8 (17) | C15—C16—H16 | 120.2 |
C11—N1—H1 | 118.4 (17) | C22—C21—C26 | 122.3 (2) |
C1—N2—C2 | 124.8 (2) | C22—C21—O2 | 117.3 (2) |
C1—N2—H2 | 115.3 (17) | C26—C21—O2 | 120.4 (2) |
C2—N2—H2 | 118.9 (17) | C21—C22—C23 | 119.2 (3) |
N2—C2—C3 | 111.6 (2) | C21—C22—H22 | 120.4 |
N2—C2—P1 | 106.6 (2) | C23—C22—H22 | 120.4 |
C3—C2—P1 | 111.9 (2) | C24—C23—C22 | 119.4 (3) |
N2—C2—H201 | 101.8 (13) | C24—C23—H23 | 120.3 |
C3—C2—H201 | 114.9 (13) | C22—C23—H23 | 120.3 |
P1—C2—H201 | 109.3 (13) | C25—C24—C23 | 120.2 (3) |
C2—C3—H301 | 109.5 | C25—C24—H24 | 119.9 |
C2—C3—H302 | 109.5 | C23—C24—H24 | 119.9 |
H301—C3—H302 | 109.5 | C24—C25—C26 | 121.3 (3) |
C2—C3—H303 | 109.5 | C24—C25—H25 | 119.3 |
H301—C3—H303 | 109.5 | C26—C25—H25 | 119.3 |
H302—C3—H303 | 109.5 | C21—C26—C25 | 117.6 (3) |
O1—P1—O2 | 115.69 (10) | C21—C26—H26 | 121.2 |
O1—P1—O3 | 114.08 (11) | C25—C26—H26 | 121.2 |
O2—P1—O3 | 102.22 (10) | C36—C31—C32 | 121.9 (3) |
O1—P1—C2 | 113.74 (12) | C36—C31—O3 | 118.4 (3) |
O2—P1—C2 | 102.43 (11) | C32—C31—O3 | 119.7 (2) |
O3—P1—C2 | 107.37 (11) | C31—C32—C33 | 118.9 (3) |
C21—O2—P1 | 122.5 (2) | C31—C32—H32 | 120.6 |
C31—O3—P1 | 123.9 (2) | C33—C32—H32 | 120.6 |
C12—C11—C16 | 119.5 (2) | C34—C33—C32 | 120.4 (4) |
C12—C11—N1 | 122.7 (2) | C34—C33—H33 | 119.8 |
C16—C11—N1 | 117.7 (2) | C32—C33—H33 | 119.8 |
C13—C12—C11 | 120.1 (3) | C33—C34—C35 | 119.7 (3) |
C13—C12—H12 | 119.95 | C33—C34—H34 | 120.2 |
C11—C12—H12 | 119.95 | C35—C34—H34 | 120.2 |
C12—C13—C14 | 120.6 (3) | C34—C35—C36 | 120.3 (4) |
C12—C13—H13 | 119.7 | C34—C35—H35 | 119.9 |
C14—C13—H13 | 119.7 | C36—C35—H35 | 119.9 |
C15—C14—C13 | 119.6 (3) | C31—C36—C35 | 118.8 (3) |
C15—C14—H14 | 120.2 | C31—C36—H36 | 120.6 |
C13—C14—H14 | 120.2 | C35—C36—H36 | 120.6 |
C14—C15—C16 | 120.5 (3) | ||
N2—C1—N1—C11 | 178.6 (3) | C13—C14—C15—C16 | −1.3 (5) |
S1—C1—N1—C11 | −1.8 (4) | C12—C11—C16—C15 | 1.2 (4) |
N1—C1—N2—C2 | 175.2 (2) | N1—C11—C16—C15 | 177.8 (3) |
S1—C1—N2—C2 | −4.4 (4) | C14—C15—C16—C11 | 0.4 (5) |
C1—N2—C2—C3 | −111.4 (3) | P1—O2—C21—C22 | 123.0 (2) |
C1—N2—C2—P1 | 126.2 (2) | P1—O2—C21—C26 | −60.7 (3) |
N2—C2—P1—O1 | 59.9 (2) | C26—C21—C22—C23 | 1.0 (4) |
C3—C2—P1—O1 | −62.3 (2) | O2—C21—C22—C23 | 177.2 (2) |
N2—C2—P1—O2 | −174.5 (2) | C21—C22—C23—C24 | −0.6 (5) |
C3—C2—P1—O2 | 63.2 (2) | C22—C23—C24—C25 | 0.3 (5) |
N2—C2—P1—O3 | −67.3 (2) | C23—C24—C25—C26 | −0.3 (5) |
C3—C2—P1—O3 | 170.5 (2) | C22—C21—C26—C25 | −1.0 (4) |
O1—P1—O2—C21 | −37.3 (2) | O2—C21—C26—C25 | −177.1 (2) |
O3—P1—O2—C21 | 87.2 (2) | C24—C25—C26—C21 | 0.6 (5) |
C2—P1—O2—C21 | −161.6 (2) | P1—O3—C31—C36 | −107.9 (3) |
O1—P1—O3—C31 | −34.7 (2) | P1—O3—C31—C32 | 74.6 (3) |
O2—P1—O3—C31 | −160.3 (2) | C36—C31—C32—C33 | 0.8 (5) |
C2—P1—O3—C31 | 92.3 (2) | O3—C31—C32—C33 | 178.2 (3) |
C1—N1—C11—C12 | −44.5 (4) | C31—C32—C33—C34 | 1.1 (6) |
C1—N1—C11—C16 | 139.0 (3) | C32—C33—C34—C35 | −1.5 (6) |
C16—C11—C12—C13 | −1.9 (4) | C33—C34—C35—C36 | 0.0 (6) |
N1—C11—C12—C13 | −178.3 (3) | C32—C31—C36—C35 | −2.3 (5) |
C11—C12—C13—C14 | 1.0 (4) | O3—C31—C36—C35 | −179.7 (3) |
C12—C13—C14—C15 | 0.6 (5) | C34—C35—C36—C31 | 1.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.90 (3) | 2.03 (3) | 2.896 (3) | 161 (3) |
N2—H2···O1i | 0.85 (3) | 2.08 (3) | 2.897 (3) | 160 (3) |
Symmetry code: (i) −x+1, −y+1, −z+1. |