Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021859/bt6693sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021859/bt6693Isup2.hkl |
CCDC reference: 282241
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.012 Å
- R factor = 0.035
- wR factor = 0.090
- Data-to-parameter ratio = 16.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for Cl1 - P1 .. 7.89 su PLAT340_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ... 12
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.390 From the CIF: _refine_ls_abs_structure_Flack_su 0.160 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.39 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for S1 - P1 .. 6.32 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27 PLAT732_ALERT_1_C Angle Calc 96.8(3), Rep 96.81(8) ...... 3.75 su-Rat O2 -P1 -O1 1.555 1.555 1.555 PLAT732_ALERT_1_C Angle Calc 114.40(10), Rep 114.41(4) ...... 2.50 su-Rat CL1 -P1 -S1 1.555 1.555 1.555
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 26.00 From the CIF: _reflns_number_total 4235 Count of symmetry unique reflns 2216 Completeness (_total/calc) 191.11% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2019 Fraction of Friedel pairs measured 0.911 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 4 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 3 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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).
C22H30ClO2PS | F(000) = 904 |
Mr = 424.94 | Dx = 1.254 Mg m−3 |
Monoclinic, Cc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C -2yc | Cell parameters from 7293 reflections |
a = 24.139 (2) Å | θ = 1.8–26.9° |
b = 8.3588 (6) Å | µ = 0.35 mm−1 |
c = 11.8747 (12) Å | T = 296 K |
β = 110.014 (8)° | Prism, colorless |
V = 2251.3 (4) Å3 | 0.25 × 0.23 × 0.20 mm |
Z = 4 |
Stoe IPDS-II diffractometer | 4235 independent reflections |
Radiation source: fine-focus sealed tube | 2583 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.063 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.0°, θmin = 1.8° |
ω scans | h = −29→29 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −10→10 |
Tmin = 0.937, Tmax = 0.961 | l = −14→14 |
14829 measured reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0477P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.090 | (Δ/σ)max < 0.001 |
S = 0.86 | Δρmax = 0.14 e Å−3 |
4235 reflections | Δρmin = −0.21 e Å−3 |
251 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0048 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.39 (16) |
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 | ||
C1 | 0.1508 (3) | 0.3442 (10) | 0.5114 (7) | 0.0485 (19) | |
C2 | 0.1273 (4) | 0.2028 (9) | 0.5417 (7) | 0.0535 (19) | |
H2 | 0.1510 | 0.1195 | 0.5836 | 0.064* | |
C3 | 0.0663 (4) | 0.1970 (12) | 0.5045 (7) | 0.068 (2) | |
H3 | 0.0494 | 0.1024 | 0.5184 | 0.081* | |
C4 | 0.0303 (3) | 0.3136 (12) | 0.4513 (7) | 0.053 (2) | |
C5 | 0.0566 (3) | 0.4515 (11) | 0.4304 (7) | 0.053 (2) | |
H5 | 0.0321 | 0.5365 | 0.3943 | 0.064* | |
C6 | 0.1190 (3) | 0.4743 (9) | 0.4601 (7) | 0.0449 (18) | |
C7 | 0.1450 (4) | 0.6314 (9) | 0.4289 (8) | 0.052 (2) | |
C8 | 0.1783 (4) | 0.5971 (10) | 0.3447 (8) | 0.067 (2) | |
H8A | 0.1930 | 0.6955 | 0.3240 | 0.100* | |
H8B | 0.1523 | 0.5472 | 0.2733 | 0.100* | |
H8C | 0.2107 | 0.5268 | 0.3831 | 0.100* | |
C9 | 0.1839 (3) | 0.7139 (9) | 0.5417 (6) | 0.0528 (19) | |
H9A | 0.1986 | 0.8122 | 0.5208 | 0.079* | |
H9B | 0.2164 | 0.6455 | 0.5832 | 0.079* | |
H9C | 0.1613 | 0.7364 | 0.5925 | 0.079* | |
C10 | 0.0979 (3) | 0.7560 (10) | 0.3633 (8) | 0.069 (2) | |
H10A | 0.0745 | 0.7820 | 0.4119 | 0.104* | |
H10B | 0.0730 | 0.7127 | 0.2882 | 0.104* | |
H10C | 0.1168 | 0.8510 | 0.3490 | 0.104* | |
C11 | −0.0354 (3) | 0.3021 (12) | 0.4223 (8) | 0.072 (3) | |
H11A | −0.0446 | 0.3189 | 0.4939 | 0.109* | |
H11B | −0.0488 | 0.1980 | 0.3905 | 0.109* | |
H11C | −0.0547 | 0.3822 | 0.3641 | 0.109* | |
C21 | 0.3712 (3) | 0.3456 (8) | 0.5866 (6) | 0.0426 (18) | |
C22 | 0.3945 (3) | 0.2089 (11) | 0.5655 (8) | 0.062 (2) | |
H22 | 0.3695 | 0.1239 | 0.5317 | 0.074* | |
C23 | 0.4555 (3) | 0.1887 (10) | 0.5923 (7) | 0.0541 (19) | |
H23 | 0.4711 | 0.0949 | 0.5733 | 0.065* | |
C24 | 0.4924 (3) | 0.3191 (11) | 0.6501 (7) | 0.052 (2) | |
C25 | 0.4667 (3) | 0.4563 (9) | 0.6764 (7) | 0.0483 (18) | |
H25 | 0.4912 | 0.5403 | 0.7146 | 0.058* | |
C26 | 0.4077 (3) | 0.4741 (8) | 0.6491 (6) | 0.0431 (18) | |
C27 | 0.3812 (3) | 0.6268 (9) | 0.6779 (8) | 0.051 (2) | |
C28 | 0.3444 (4) | 0.5893 (11) | 0.7594 (7) | 0.068 (2) | |
H28A | 0.3123 | 0.5197 | 0.7176 | 0.102* | |
H28B | 0.3292 | 0.6870 | 0.7795 | 0.102* | |
H28C | 0.3691 | 0.5378 | 0.8313 | 0.102* | |
C29 | 0.3412 (3) | 0.7053 (10) | 0.5586 (8) | 0.073 (3) | |
H29A | 0.3104 | 0.6322 | 0.5165 | 0.109* | |
H29B | 0.3645 | 0.7304 | 0.5096 | 0.109* | |
H29C | 0.3241 | 0.8016 | 0.5762 | 0.109* | |
C30 | 0.4305 (4) | 0.7436 (10) | 0.7451 (10) | 0.088 (3) | |
H30A | 0.4134 | 0.8398 | 0.7629 | 0.132* | |
H30B | 0.4537 | 0.7688 | 0.6959 | 0.132* | |
H30C | 0.4552 | 0.6952 | 0.8184 | 0.132* | |
C31 | 0.5586 (3) | 0.3017 (11) | 0.6893 (8) | 0.066 (2) | |
H31A | 0.5747 | 0.2945 | 0.7751 | 0.099* | |
H31B | 0.5750 | 0.3930 | 0.6630 | 0.099* | |
H31C | 0.5682 | 0.2065 | 0.6547 | 0.099* | |
O1 | 0.2141 (2) | 0.3630 (6) | 0.5535 (5) | 0.0508 (14) | |
O2 | 0.3106 (2) | 0.3636 (6) | 0.5522 (5) | 0.0528 (15) | |
P1 | 0.26315 (15) | 0.23937 (7) | 0.5520 (3) | 0.05266 (19) | |
S1 | 0.23776 (8) | 0.1118 (3) | 0.40487 (18) | 0.0701 (7) | |
Cl1 | 0.28846 (8) | 0.1143 (3) | 0.69852 (17) | 0.0763 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.038 (4) | 0.053 (4) | 0.055 (4) | −0.012 (3) | 0.016 (3) | −0.015 (3) |
C2 | 0.070 (5) | 0.037 (3) | 0.059 (4) | 0.000 (3) | 0.029 (4) | 0.012 (3) |
C3 | 0.067 (5) | 0.076 (6) | 0.066 (5) | −0.031 (4) | 0.032 (4) | −0.011 (4) |
C4 | 0.055 (4) | 0.061 (5) | 0.052 (5) | −0.018 (4) | 0.029 (4) | −0.011 (4) |
C5 | 0.035 (3) | 0.069 (5) | 0.053 (5) | 0.000 (4) | 0.010 (3) | −0.005 (4) |
C6 | 0.038 (4) | 0.045 (4) | 0.055 (4) | −0.007 (3) | 0.020 (3) | −0.013 (3) |
C7 | 0.047 (4) | 0.044 (4) | 0.061 (5) | −0.007 (3) | 0.013 (4) | 0.008 (4) |
C8 | 0.063 (5) | 0.050 (4) | 0.087 (6) | 0.005 (3) | 0.024 (4) | 0.021 (4) |
C9 | 0.041 (4) | 0.050 (4) | 0.061 (4) | 0.008 (3) | 0.011 (3) | 0.001 (3) |
C10 | 0.045 (3) | 0.061 (4) | 0.090 (5) | 0.012 (3) | 0.007 (3) | 0.006 (3) |
C11 | 0.042 (4) | 0.088 (6) | 0.085 (5) | −0.023 (4) | 0.019 (4) | −0.010 (5) |
C21 | 0.039 (4) | 0.040 (4) | 0.042 (4) | 0.000 (3) | 0.005 (3) | −0.007 (3) |
C22 | 0.045 (4) | 0.062 (5) | 0.069 (5) | 0.011 (3) | 0.008 (3) | −0.003 (4) |
C23 | 0.057 (4) | 0.039 (3) | 0.067 (5) | 0.004 (3) | 0.022 (3) | −0.011 (3) |
C24 | 0.040 (4) | 0.059 (5) | 0.059 (5) | 0.008 (3) | 0.017 (3) | 0.011 (4) |
C25 | 0.049 (4) | 0.039 (4) | 0.060 (5) | 0.005 (3) | 0.022 (4) | 0.001 (3) |
C26 | 0.044 (4) | 0.045 (4) | 0.037 (3) | −0.003 (3) | 0.008 (3) | −0.010 (3) |
C27 | 0.035 (4) | 0.048 (4) | 0.070 (5) | −0.007 (3) | 0.019 (4) | −0.014 (4) |
C28 | 0.065 (5) | 0.095 (6) | 0.053 (4) | 0.006 (4) | 0.032 (4) | −0.009 (4) |
C29 | 0.063 (5) | 0.045 (4) | 0.120 (7) | 0.020 (3) | 0.043 (5) | 0.012 (4) |
C30 | 0.066 (5) | 0.062 (4) | 0.132 (8) | 0.001 (3) | 0.027 (5) | −0.054 (4) |
C31 | 0.061 (5) | 0.073 (5) | 0.081 (5) | 0.019 (4) | 0.047 (4) | 0.027 (4) |
O1 | 0.036 (3) | 0.043 (3) | 0.070 (4) | −0.002 (2) | 0.013 (2) | 0.000 (3) |
O2 | 0.041 (3) | 0.041 (3) | 0.067 (4) | −0.006 (2) | 0.006 (3) | 0.003 (3) |
P1 | 0.0500 (4) | 0.0378 (3) | 0.0720 (4) | 0.0012 (13) | 0.0232 (3) | −0.0003 (14) |
S1 | 0.0741 (15) | 0.0654 (14) | 0.0722 (15) | −0.0112 (12) | 0.0269 (12) | −0.0198 (13) |
Cl1 | 0.0813 (16) | 0.0753 (15) | 0.0717 (15) | 0.0201 (13) | 0.0254 (12) | 0.0253 (13) |
C1—C6 | 1.350 (10) | C21—C26 | 1.426 (9) |
C1—C2 | 1.410 (11) | C22—C23 | 1.406 (11) |
C1—O1 | 1.444 (9) | C22—H22 | 0.9300 |
C2—C3 | 1.385 (11) | C23—C24 | 1.425 (11) |
C2—H2 | 0.9300 | C23—H23 | 0.9300 |
C3—C4 | 1.315 (12) | C24—C25 | 1.390 (11) |
C3—H3 | 0.9300 | C24—C31 | 1.511 (10) |
C4—C5 | 1.379 (12) | C25—C26 | 1.357 (10) |
C4—C11 | 1.506 (10) | C25—H25 | 0.9300 |
C5—C6 | 1.437 (10) | C26—C27 | 1.518 (10) |
C5—H5 | 0.9300 | C27—C30 | 1.534 (10) |
C6—C7 | 1.555 (11) | C27—C28 | 1.552 (11) |
C7—C8 | 1.509 (13) | C27—C29 | 1.560 (11) |
C7—C9 | 1.513 (10) | C28—H28A | 0.9600 |
C7—C10 | 1.543 (10) | C28—H28B | 0.9600 |
C8—H8A | 0.9600 | C28—H28C | 0.9600 |
C8—H8B | 0.9600 | C29—H29A | 0.9600 |
C8—H8C | 0.9600 | C29—H29B | 0.9600 |
C9—H9A | 0.9600 | C29—H29C | 0.9600 |
C9—H9B | 0.9600 | C30—H30A | 0.9600 |
C9—H9C | 0.9600 | C30—H30B | 0.9600 |
C10—H10A | 0.9600 | C30—H30C | 0.9600 |
C10—H10B | 0.9600 | C31—H31A | 0.9600 |
C10—H10C | 0.9600 | C31—H31B | 0.9600 |
C11—H11A | 0.9600 | C31—H31C | 0.9600 |
C11—H11B | 0.9600 | O1—P1 | 1.576 (6) |
C11—H11C | 0.9600 | O2—P1 | 1.545 (6) |
C21—C22 | 1.336 (11) | P1—Cl1 | 1.941 (4) |
C21—O2 | 1.385 (9) | P1—S1 | 1.957 (4) |
C6—C1—C2 | 125.0 (7) | C21—C22—H22 | 118.8 |
C6—C1—O1 | 116.0 (7) | C23—C22—H22 | 118.8 |
C2—C1—O1 | 118.3 (7) | C22—C23—C24 | 116.7 (7) |
C3—C2—C1 | 115.1 (7) | C22—C23—H23 | 121.6 |
C3—C2—H2 | 122.4 | C24—C23—H23 | 121.6 |
C1—C2—H2 | 122.4 | C25—C24—C23 | 119.1 (7) |
C4—C3—C2 | 125.7 (8) | C25—C24—C31 | 121.1 (8) |
C4—C3—H3 | 117.2 | C23—C24—C31 | 119.7 (8) |
C2—C3—H3 | 117.2 | C26—C25—C24 | 123.4 (7) |
C3—C4—C5 | 115.8 (8) | C26—C25—H25 | 118.3 |
C3—C4—C11 | 122.3 (8) | C24—C25—H25 | 118.3 |
C5—C4—C11 | 121.8 (8) | C25—C26—C21 | 116.9 (7) |
C4—C5—C6 | 125.1 (8) | C25—C26—C27 | 121.8 (6) |
C4—C5—H5 | 117.4 | C21—C26—C27 | 121.2 (6) |
C6—C5—H5 | 117.4 | C26—C27—C30 | 109.9 (6) |
C1—C6—C5 | 113.0 (7) | C26—C27—C28 | 110.2 (7) |
C1—C6—C7 | 125.1 (7) | C30—C27—C28 | 108.2 (8) |
C5—C6—C7 | 121.9 (7) | C26—C27—C29 | 109.0 (7) |
C8—C7—C9 | 111.4 (7) | C30—C27—C29 | 109.5 (7) |
C8—C7—C10 | 105.1 (7) | C28—C27—C29 | 110.0 (7) |
C9—C7—C10 | 105.4 (6) | C27—C28—H28A | 109.5 |
C8—C7—C6 | 110.3 (7) | C27—C28—H28B | 109.5 |
C9—C7—C6 | 110.7 (7) | H28A—C28—H28B | 109.5 |
C10—C7—C6 | 113.7 (7) | C27—C28—H28C | 109.5 |
C7—C8—H8A | 109.5 | H28A—C28—H28C | 109.5 |
C7—C8—H8B | 109.5 | H28B—C28—H28C | 109.5 |
H8A—C8—H8B | 109.5 | C27—C29—H29A | 109.5 |
C7—C8—H8C | 109.5 | C27—C29—H29B | 109.5 |
H8A—C8—H8C | 109.5 | H29A—C29—H29B | 109.5 |
H8B—C8—H8C | 109.5 | C27—C29—H29C | 109.5 |
C7—C9—H9A | 109.5 | H29A—C29—H29C | 109.5 |
C7—C9—H9B | 109.5 | H29B—C29—H29C | 109.5 |
H9A—C9—H9B | 109.5 | C27—C30—H30A | 109.5 |
C7—C9—H9C | 109.5 | C27—C30—H30B | 109.5 |
H9A—C9—H9C | 109.5 | H30A—C30—H30B | 109.5 |
H9B—C9—H9C | 109.5 | C27—C30—H30C | 109.5 |
C7—C10—H10A | 109.5 | H30A—C30—H30C | 109.5 |
C7—C10—H10B | 109.5 | H30B—C30—H30C | 109.5 |
H10A—C10—H10B | 109.5 | C24—C31—H31A | 109.5 |
C7—C10—H10C | 109.5 | C24—C31—H31B | 109.5 |
H10A—C10—H10C | 109.5 | H31A—C31—H31B | 109.5 |
H10B—C10—H10C | 109.5 | C24—C31—H31C | 109.5 |
C4—C11—H11A | 109.5 | H31A—C31—H31C | 109.5 |
C4—C11—H11B | 109.5 | H31B—C31—H31C | 109.5 |
H11A—C11—H11B | 109.5 | C1—O1—P1 | 129.4 (5) |
C4—C11—H11C | 109.5 | C21—O2—P1 | 129.4 (5) |
H11A—C11—H11C | 109.5 | O2—P1—O1 | 96.81 (8) |
H11B—C11—H11C | 109.5 | O2—P1—Cl1 | 110.8 (3) |
C22—C21—O2 | 120.6 (6) | O1—P1—Cl1 | 110.5 (3) |
C22—C21—C26 | 121.1 (7) | O2—P1—S1 | 111.9 (3) |
O2—C21—C26 | 118.3 (6) | O1—P1—S1 | 111.1 (3) |
C21—C22—C23 | 122.5 (8) | Cl1—P1—S1 | 114.41 (4) |
C6—C1—C2—C3 | 6.0 (13) | C23—C24—C25—C26 | −0.5 (12) |
O1—C1—C2—C3 | 176.3 (7) | C31—C24—C25—C26 | −176.2 (7) |
C1—C2—C3—C4 | −4.2 (13) | C24—C25—C26—C21 | −2.2 (11) |
C2—C3—C4—C5 | 0.9 (13) | C24—C25—C26—C27 | −179.3 (8) |
C2—C3—C4—C11 | −175.1 (8) | C22—C21—C26—C25 | 5.6 (12) |
C3—C4—C5—C6 | 1.2 (12) | O2—C21—C26—C25 | −176.8 (7) |
C11—C4—C5—C6 | 177.3 (7) | C22—C21—C26—C27 | −177.3 (8) |
C2—C1—C6—C5 | −4.1 (12) | O2—C21—C26—C27 | 0.3 (11) |
O1—C1—C6—C5 | −174.7 (6) | C25—C26—C27—C30 | −3.0 (11) |
C2—C1—C6—C7 | 178.8 (8) | C21—C26—C27—C30 | 180.0 (8) |
O1—C1—C6—C7 | 8.3 (12) | C25—C26—C27—C28 | −122.2 (8) |
C4—C5—C6—C1 | 0.4 (11) | C21—C26—C27—C28 | 60.9 (10) |
C4—C5—C6—C7 | 177.5 (8) | C25—C26—C27—C29 | 117.0 (8) |
C1—C6—C7—C8 | 58.4 (11) | C21—C26—C27—C29 | −60.0 (10) |
C5—C6—C7—C8 | −118.4 (8) | C6—C1—O1—P1 | −143.4 (6) |
C1—C6—C7—C9 | −65.3 (10) | C2—C1—O1—P1 | 45.4 (10) |
C5—C6—C7—C9 | 117.8 (8) | C22—C21—O2—P1 | 36.2 (11) |
C1—C6—C7—C10 | 176.2 (8) | C26—C21—O2—P1 | −141.5 (7) |
C5—C6—C7—C10 | −0.6 (11) | C21—O2—P1—O1 | 158.4 (5) |
O2—C21—C22—C23 | 176.1 (7) | C21—O2—P1—Cl1 | 43.4 (7) |
C26—C21—C22—C23 | −6.3 (13) | C21—O2—P1—S1 | −85.5 (7) |
C21—C22—C23—C24 | 3.4 (13) | C1—O1—P1—O2 | 154.8 (5) |
C22—C23—C24—C25 | 0.0 (12) | C1—O1—P1—Cl1 | −90.0 (6) |
C22—C23—C24—C31 | 175.8 (7) | C1—O1—P1—S1 | 38.1 (7) |