Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802004567/ya6095sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802004567/ya60956sup2.hkl |
CCDC reference: 183807
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.074
- wR factor = 0.170
- Data-to-parameter ratio = 17.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
ABSMU_01 Alert C The ratio of given/expected absorption coefficient lies outside the range 0.99 <> 1.01 Calculated value of mu = 0.176 Value of mu given = 0.180
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: SMART-NT (Bruker 1998); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Bruker, 1999); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 1990); software used to prepare material for publication: SHELXTL.
C17H27O7P | F(000) = 1600 |
Mr = 374.36 | Dx = 1.286 Mg m−3 |
Monoclinic, C2/c | Melting point: 348 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71073 Å |
a = 19.7987 (11) Å | Cell parameters from 1024 reflections |
b = 11.2320 (5) Å | θ = 2.1–27.0° |
c = 19.3329 (11) Å | µ = 0.18 mm−1 |
β = 115.880 (2)° | T = 296 K |
V = 3868.1 (4) Å3 | Needle, colourless |
Z = 8 | 0.40 × 0.08 × 0.08 mm |
Bruker SMART 1K CCD diffractometer | 4155 independent reflections |
Radiation source: fine-focus sealed tube | 2976 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
ω scans | θmax = 27.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −24→25 |
Tmin = 0.933, Tmax = 0.986 | k = −11→14 |
11051 measured reflections | l = −24→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.074 | w = 1/[σ2(Fo2) + (0.0544P)2 + 5.2563P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.170 | (Δ/σ)max < 0.001 |
S = 1.15 | Δρmax = 0.55 e Å−3 |
4155 reflections | Δρmin = −0.25 e Å−3 |
232 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 | ||
P1 | 0.14471 (4) | 0.35847 (7) | 0.15345 (5) | 0.0420 (2) | |
C1 | 0.0019 (2) | 0.8164 (3) | 0.1294 (2) | 0.0580 (9) | |
H1 | 0.0047 | 0.8467 | 0.1781 | 0.070* | |
O2 | 0.07307 (14) | 0.8424 (2) | 0.12900 (15) | 0.0629 (7) | |
C3 | 0.0848 (2) | 0.7821 (3) | 0.0710 (2) | 0.0570 (9) | |
H3 | 0.0418 | 0.7969 | 0.0213 | 0.068* | |
C4 | 0.09110 (18) | 0.6503 (3) | 0.08651 (19) | 0.0482 (7) | |
H4A | 0.0870 | 0.6087 | 0.0409 | 0.058* | |
H4B | 0.1402 | 0.6331 | 0.1276 | 0.058* | |
C4A | 0.03190 (16) | 0.6043 (3) | 0.10861 (16) | 0.0401 (7) | |
C5 | 0.02111 (16) | 0.4825 (3) | 0.11243 (16) | 0.0404 (7) | |
C6 | −0.03192 (16) | 0.4375 (3) | 0.13388 (17) | 0.0431 (7) | |
C7 | −0.07500 (16) | 0.5155 (3) | 0.15376 (17) | 0.0462 (7) | |
H7 | −0.1106 | 0.4868 | 0.1688 | 0.055* | |
C8 | −0.06410 (18) | 0.6369 (3) | 0.15075 (18) | 0.0473 (7) | |
C8A | −0.01116 (17) | 0.6829 (3) | 0.12856 (17) | 0.0453 (7) | |
C9 | −0.0609 (2) | 0.8817 (4) | 0.0664 (3) | 0.0847 (13) | |
H9A | −0.0507 | 0.9656 | 0.0716 | 0.127* | |
H9B | −0.1071 | 0.8662 | 0.0697 | 0.127* | |
H9C | −0.0652 | 0.8551 | 0.0174 | 0.127* | |
C10 | 0.1539 (3) | 0.8346 (4) | 0.0693 (3) | 0.0790 (12) | |
H10A | 0.1456 | 0.9175 | 0.0561 | 0.119* | |
H10B | 0.1647 | 0.7936 | 0.0317 | 0.119* | |
H10C | 0.1956 | 0.8263 | 0.1190 | 0.119* | |
O11 | 0.06392 (11) | 0.40114 (18) | 0.09216 (11) | 0.0436 (5) | |
O12 | 0.16169 (12) | 0.3888 (2) | 0.23232 (12) | 0.0528 (6) | |
O13 | 0.20135 (11) | 0.4137 (2) | 0.12625 (12) | 0.0498 (5) | |
C14 | 0.1954 (2) | 0.3978 (4) | 0.0495 (2) | 0.0643 (10) | |
H14A | 0.1436 | 0.4067 | 0.0118 | 0.077* | |
H14B | 0.2123 | 0.3187 | 0.0442 | 0.077* | |
C15 | 0.2433 (2) | 0.4898 (4) | 0.0369 (3) | 0.0884 (14) | |
H15A | 0.2239 | 0.5676 | 0.0386 | 0.133* | |
H15B | 0.2430 | 0.4776 | −0.0123 | 0.133* | |
H15C | 0.2938 | 0.4834 | 0.0765 | 0.133* | |
O16 | 0.14601 (13) | 0.22405 (19) | 0.13352 (13) | 0.0557 (6) | |
C17 | 0.1117 (2) | 0.1345 (3) | 0.1626 (2) | 0.0599 (9) | |
H17A | 0.0882 | 0.0737 | 0.1237 | 0.072* | |
H17B | 0.0729 | 0.1713 | 0.1733 | 0.072* | |
C18 | 0.1684 (3) | 0.0786 (4) | 0.2337 (2) | 0.0819 (13) | |
H18A | 0.2061 | 0.0404 | 0.2228 | 0.123* | |
H18B | 0.1445 | 0.0206 | 0.2520 | 0.123* | |
H18C | 0.1914 | 0.1386 | 0.2722 | 0.123* | |
O19 | −0.03771 (13) | 0.31574 (19) | 0.13397 (14) | 0.0571 (6) | |
C20 | −0.0928 (2) | 0.2657 (3) | 0.1537 (3) | 0.0728 (11) | |
H20A | −0.0836 | 0.2911 | 0.2045 | 0.109* | |
H20B | −0.0902 | 0.1805 | 0.1525 | 0.109* | |
H20C | −0.1417 | 0.2918 | 0.1176 | 0.109* | |
O21 | −0.10346 (14) | 0.7204 (2) | 0.17059 (15) | 0.0642 (7) | |
C22 | −0.1588 (2) | 0.6797 (4) | 0.1933 (2) | 0.0631 (10) | |
H22A | −0.1985 | 0.6407 | 0.1508 | 0.095* | |
H22B | −0.1790 | 0.7463 | 0.2094 | 0.095* | |
H22C | −0.1364 | 0.6247 | 0.2353 | 0.095* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0448 (4) | 0.0363 (4) | 0.0455 (4) | 0.0036 (3) | 0.0205 (3) | 0.0001 (3) |
C1 | 0.066 (2) | 0.0428 (18) | 0.077 (2) | 0.0066 (16) | 0.0412 (19) | 0.0026 (17) |
O2 | 0.0706 (16) | 0.0466 (14) | 0.0780 (17) | −0.0038 (12) | 0.0383 (14) | −0.0031 (12) |
C3 | 0.066 (2) | 0.0455 (19) | 0.065 (2) | 0.0006 (16) | 0.0338 (18) | 0.0059 (16) |
C4 | 0.0543 (19) | 0.0444 (18) | 0.0497 (18) | −0.0027 (15) | 0.0263 (15) | 0.0004 (14) |
C4A | 0.0412 (16) | 0.0403 (16) | 0.0385 (16) | 0.0008 (13) | 0.0172 (13) | 0.0018 (12) |
C5 | 0.0381 (15) | 0.0410 (17) | 0.0413 (16) | 0.0031 (13) | 0.0165 (13) | −0.0030 (13) |
C6 | 0.0429 (17) | 0.0405 (17) | 0.0449 (17) | 0.0011 (13) | 0.0182 (14) | 0.0039 (13) |
C7 | 0.0368 (16) | 0.055 (2) | 0.0474 (17) | 0.0036 (14) | 0.0193 (14) | 0.0058 (15) |
C8 | 0.0495 (18) | 0.0474 (18) | 0.0466 (17) | 0.0111 (15) | 0.0224 (14) | 0.0051 (15) |
C8A | 0.0475 (17) | 0.0428 (17) | 0.0472 (17) | 0.0038 (14) | 0.0220 (14) | 0.0014 (14) |
C9 | 0.080 (3) | 0.063 (3) | 0.107 (3) | 0.020 (2) | 0.037 (3) | 0.023 (2) |
C10 | 0.100 (3) | 0.058 (2) | 0.107 (3) | −0.007 (2) | 0.071 (3) | 0.007 (2) |
O11 | 0.0449 (12) | 0.0416 (11) | 0.0460 (12) | 0.0029 (9) | 0.0214 (10) | −0.0042 (9) |
O12 | 0.0584 (14) | 0.0543 (14) | 0.0452 (12) | 0.0063 (11) | 0.0221 (11) | −0.0004 (10) |
O13 | 0.0455 (12) | 0.0544 (13) | 0.0520 (13) | 0.0007 (10) | 0.0236 (10) | 0.0003 (10) |
C14 | 0.068 (2) | 0.077 (3) | 0.060 (2) | 0.000 (2) | 0.0386 (19) | 0.0013 (19) |
C15 | 0.075 (3) | 0.117 (4) | 0.090 (3) | −0.011 (3) | 0.052 (3) | 0.010 (3) |
O16 | 0.0686 (15) | 0.0377 (12) | 0.0679 (15) | 0.0083 (11) | 0.0362 (12) | 0.0000 (11) |
C17 | 0.066 (2) | 0.0392 (18) | 0.074 (2) | −0.0018 (16) | 0.0307 (19) | −0.0025 (17) |
C18 | 0.098 (3) | 0.062 (3) | 0.078 (3) | 0.012 (2) | 0.031 (3) | 0.017 (2) |
O19 | 0.0655 (15) | 0.0423 (12) | 0.0773 (16) | −0.0039 (11) | 0.0439 (13) | 0.0001 (11) |
C20 | 0.088 (3) | 0.055 (2) | 0.099 (3) | −0.014 (2) | 0.063 (3) | −0.002 (2) |
O21 | 0.0689 (16) | 0.0550 (15) | 0.0873 (18) | 0.0161 (12) | 0.0514 (14) | 0.0063 (13) |
C22 | 0.057 (2) | 0.074 (2) | 0.067 (2) | 0.0153 (19) | 0.0351 (19) | 0.0045 (19) |
P1—O12 | 1.451 (2) | C9—H9C | 0.9600 |
P1—O13 | 1.560 (2) | C10—H10A | 0.9600 |
P1—O16 | 1.561 (2) | C10—H10B | 0.9600 |
P1—O11 | 1.593 (2) | C10—H10C | 0.9600 |
C1—O2 | 1.442 (4) | O13—C14 | 1.448 (4) |
C1—C9 | 1.499 (5) | C14—C15 | 1.493 (5) |
C1—C8A | 1.521 (5) | C14—H14A | 0.9700 |
C1—H1 | 0.9800 | C14—H14B | 0.9700 |
O2—C3 | 1.413 (4) | C15—H15A | 0.9600 |
C3—C10 | 1.503 (5) | C15—H15B | 0.9600 |
C3—C4 | 1.505 (4) | C15—H15C | 0.9600 |
C3—H3 | 0.9800 | O16—C17 | 1.457 (4) |
C4—C4A | 1.503 (4) | C17—C18 | 1.482 (5) |
C4—H4A | 0.9700 | C17—H17A | 0.9700 |
C4—H4B | 0.9700 | C17—H17B | 0.9700 |
C4A—C5 | 1.392 (4) | C18—H18A | 0.9600 |
C4A—C8A | 1.394 (4) | C18—H18B | 0.9600 |
C5—C6 | 1.382 (4) | C18—H18C | 0.9600 |
C5—O11 | 1.413 (3) | O19—C20 | 1.418 (4) |
C6—O19 | 1.373 (4) | C20—H20A | 0.9600 |
C6—C7 | 1.389 (4) | C20—H20B | 0.9600 |
C7—C8 | 1.385 (4) | C20—H20C | 0.9600 |
C7—H7 | 0.9300 | O21—C22 | 1.423 (4) |
C8—O21 | 1.377 (4) | C22—H22A | 0.9600 |
C8—C8A | 1.394 (4) | C22—H22B | 0.9600 |
C9—H9A | 0.9600 | C22—H22C | 0.9600 |
C9—H9B | 0.9600 | ||
O12—P1—O13 | 112.94 (13) | H9B—C9—H9C | 109.5 |
O12—P1—O16 | 117.72 (13) | C3—C10—H10A | 109.5 |
O13—P1—O16 | 102.10 (13) | C3—C10—H10B | 109.5 |
O12—P1—O11 | 114.07 (12) | H10A—C10—H10B | 109.5 |
O13—P1—O11 | 105.41 (12) | C3—C10—H10C | 109.5 |
O16—P1—O11 | 103.11 (12) | H10A—C10—H10C | 109.5 |
O2—C1—C9 | 111.3 (3) | H10B—C10—H10C | 109.5 |
O2—C1—C8A | 111.2 (3) | C5—O11—P1 | 121.15 (18) |
C9—C1—C8A | 113.4 (3) | C14—O13—P1 | 123.2 (2) |
O2—C1—H1 | 106.8 | O13—C14—C15 | 107.9 (3) |
C9—C1—H1 | 106.8 | O13—C14—H14A | 110.1 |
C8A—C1—H1 | 106.8 | C15—C14—H14A | 110.1 |
C3—O2—C1 | 113.9 (3) | O13—C14—H14B | 110.1 |
O2—C3—C10 | 107.2 (3) | C15—C14—H14B | 110.1 |
O2—C3—C4 | 110.0 (3) | H14A—C14—H14B | 108.4 |
C10—C3—C4 | 113.1 (3) | C14—C15—H15A | 109.5 |
O2—C3—H3 | 108.8 | C14—C15—H15B | 109.5 |
C10—C3—H3 | 108.8 | H15A—C15—H15B | 109.5 |
C4—C3—H3 | 108.8 | C14—C15—H15C | 109.5 |
C4A—C4—C3 | 112.8 (3) | H15A—C15—H15C | 109.5 |
C4A—C4—H4A | 109.0 | H15B—C15—H15C | 109.5 |
C3—C4—H4A | 109.0 | C17—O16—P1 | 120.8 (2) |
C4A—C4—H4B | 109.0 | O16—C17—C18 | 110.9 (3) |
C3—C4—H4B | 109.0 | O16—C17—H17A | 109.5 |
H4A—C4—H4B | 107.8 | C18—C17—H17A | 109.5 |
C5—C4A—C8A | 118.8 (3) | O16—C17—H17B | 109.5 |
C5—C4A—C4 | 120.7 (3) | C18—C17—H17B | 109.5 |
C8A—C4A—C4 | 120.5 (3) | H17A—C17—H17B | 108.0 |
C6—C5—C4A | 122.0 (3) | C17—C18—H18A | 109.5 |
C6—C5—O11 | 118.3 (3) | C17—C18—H18B | 109.5 |
C4A—C5—O11 | 119.7 (3) | H18A—C18—H18B | 109.5 |
O19—C6—C5 | 116.0 (3) | C17—C18—H18C | 109.5 |
O19—C6—C7 | 124.5 (3) | H18A—C18—H18C | 109.5 |
C5—C6—C7 | 119.5 (3) | H18B—C18—H18C | 109.5 |
C8—C7—C6 | 118.9 (3) | C6—O19—C20 | 118.0 (3) |
C8—C7—H7 | 120.6 | O19—C20—H20A | 109.5 |
C6—C7—H7 | 120.6 | O19—C20—H20B | 109.5 |
O21—C8—C7 | 122.8 (3) | H20A—C20—H20B | 109.5 |
O21—C8—C8A | 115.2 (3) | O19—C20—H20C | 109.5 |
C7—C8—C8A | 122.0 (3) | H20A—C20—H20C | 109.5 |
C4A—C8A—C8 | 118.9 (3) | H20B—C20—H20C | 109.5 |
C4A—C8A—C1 | 120.4 (3) | C8—O21—C22 | 118.2 (3) |
C8—C8A—C1 | 120.7 (3) | O21—C22—H22A | 109.5 |
C1—C9—H9A | 109.5 | O21—C22—H22B | 109.5 |
C1—C9—H9B | 109.5 | H22A—C22—H22B | 109.5 |
H9A—C9—H9B | 109.5 | O21—C22—H22C | 109.5 |
C1—C9—H9C | 109.5 | H22A—C22—H22C | 109.5 |
H9A—C9—H9C | 109.5 | H22B—C22—H22C | 109.5 |
C9—C1—O2—C3 | −76.9 (4) | C7—C8—C8A—C4A | 0.2 (5) |
C8A—C1—O2—C3 | 50.5 (4) | O21—C8—C8A—C1 | 1.7 (4) |
C1—O2—C3—C10 | 170.2 (3) | C7—C8—C8A—C1 | −177.2 (3) |
C1—O2—C3—C4 | −66.5 (4) | O2—C1—C8A—C4A | −16.0 (4) |
O2—C3—C4—C4A | 45.1 (4) | C9—C1—C8A—C4A | 110.3 (4) |
C10—C3—C4—C4A | 164.9 (3) | O2—C1—C8A—C8 | 161.4 (3) |
C3—C4—C4A—C5 | 169.1 (3) | C9—C1—C8A—C8 | −72.3 (4) |
C3—C4—C4A—C8A | −13.4 (4) | C6—C5—O11—P1 | −95.3 (3) |
C8A—C4A—C5—C6 | 1.3 (4) | C4A—C5—O11—P1 | 86.2 (3) |
C4—C4A—C5—C6 | 178.8 (3) | O12—P1—O11—C5 | 12.7 (3) |
C8A—C4A—C5—O11 | 179.7 (2) | O13—P1—O11—C5 | −111.7 (2) |
C4—C4A—C5—O11 | −2.8 (4) | O16—P1—O11—C5 | 141.6 (2) |
C4A—C5—C6—O19 | 178.9 (3) | O12—P1—O13—C14 | −178.9 (2) |
O11—C5—C6—O19 | 0.5 (4) | O16—P1—O13—C14 | 53.7 (3) |
C4A—C5—C6—C7 | −1.3 (4) | O11—P1—O13—C14 | −53.8 (3) |
O11—C5—C6—C7 | −179.7 (3) | P1—O13—C14—C15 | 163.4 (3) |
O19—C6—C7—C8 | −179.5 (3) | O12—P1—O16—C17 | 43.9 (3) |
C5—C6—C7—C8 | 0.7 (4) | O13—P1—O16—C17 | 168.2 (2) |
C6—C7—C8—O21 | −179.0 (3) | O11—P1—O16—C17 | −82.6 (2) |
C6—C7—C8—C8A | −0.2 (5) | P1—O16—C17—C18 | −96.1 (3) |
C5—C4A—C8A—C8 | −0.8 (4) | C5—C6—O19—C20 | −178.4 (3) |
C4—C4A—C8A—C8 | −178.3 (3) | C7—C6—O19—C20 | 1.8 (5) |
C5—C4A—C8A—C1 | 176.6 (3) | C7—C8—O21—C22 | −1.5 (5) |
C4—C4A—C8A—C1 | −0.9 (5) | C8A—C8—O21—C22 | 179.6 (3) |
O21—C8—C8A—C4A | 179.1 (3) |
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