Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807015954/sj2278sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807015954/sj2278Isup2.hkl |
CCDC reference: 647344
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.049
- wR factor = 0.117
- Data-to-parameter ratio = 10.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C19
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 2 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 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ZORTEPII (Zsolnai, 1998); software used to prepare material for publication: enCIFer (Allen et al., 2004) and PARST (Nardelli, 1995).
C15H15O4P | F(000) = 608 |
Mr = 290.24 | Dx = 1.385 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 899 reflections |
a = 9.4405 (10) Å | θ = 2.7–25.0° |
b = 15.2017 (16) Å | µ = 0.21 mm−1 |
c = 9.7458 (10) Å | T = 293 K |
β = 95.782 (2)° | Block, colourless |
V = 1391.5 (3) Å3 | 0.38 × 0.34 × 0.20 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 2457 independent reflections |
Radiation source: fine-focus sealed tube | 2304 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
ω scans | θmax = 25.0°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −11→11 |
Tmin = 0.836, Tmax = 0.959 | k = −18→18 |
16173 measured reflections | l = −11→11 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0447P)2 + 0.6861P] where P = (Fo2 + 2Fc2)/3 |
2457 reflections | (Δ/σ)max = 0.001 |
229 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
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. Weighted least-squares planes through the starred atoms (Nardelli, Musatti, Domiano & Andreetti Ric·Sci.(1965),15(II—A),807). Equation of the plane: m1*X+m2*Y+m3*Z=d Plane 1 m1 = 0.93156(0.00033) m2 = -0.35147(0.00106) m3 = -0.09310(0.00140) D = 7.87977(0.00445) Atom d s d/s (d/s)**2 C1 * 0.0022 0.0026 0.822 0.676 O2 * -0.0010 0.0016 - 0.588 0.346 O4 * 0.0009 0.0016 0.585 0.342 C5 * -0.0028 0.0030 - 0.921 0.848 P3 - 0.6538 0.0007 - 988.862 977847.938 C10 1.0604 0.0023 461.164 212672.375 C11 1.0609 0.0024 445.972 198890.984 ============ Sum((d/s)**2) for starred atoms 2.213 Chi-squared at 95% for 1 degrees of freedom: 3.84 The group of atoms does not deviate significantly from planarity Plane 2 m1 = 0.87853(0.00031) m2 = -0.02578(0.00067) m3 = -0.47700(0.00057) D = 7.15991(0.00458) Atom d s d/s (d/s)**2 P3 * -0.0353 0.0007 - 54.229 2940.818 O2 * 0.2282 0.0016 144.487 20876.410 C1 * -0.4722 0.0026 - 178.251 31773.379 C10 * 0.0996 0.0023 43.477 1890.286 C11 * 0.0932 0.0023 39.824 1585.980 C5 * -0.4982 0.0029 - 171.515 29417.547 O4 * 0.2167 0.0016 133.471 17814.400 ============ Sum((d/s)**2) for starred atoms 106298.820 Chi-squared at 95% for 4 degrees of freedom: 9.49 The group of atoms deviates significantly from planarity Plane 3 m1 = 0.66149(0.00083) m2 = 0.25768(0.00116) m3 = -0.70429(0.00077) D = 4.42869(0.01154) Atom d s d/s (d/s)**2 C6 * 0.0143 0.0028 5.167 26.695 C7 * -0.0063 0.0031 - 2.033 4.133 C8 * -0.0116 0.0032 - 3.606 13.001 C9 * 0.0140 0.0029 4.821 23.242 C10 * -0.0024 0.0023 - 1.018 1.035 C11 * -0.0070 0.0023 - 3.023 9.139 ============ Sum((d/s)**2) for starred atoms 77.245 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms deviates significantly from planarity Plane 4 m1 = -0.03113(0.00106) m2 = 0.92495(0.00040) m3 = -0.37881(0.00099) D = 1.66993(0.00585) Atom d s d/s (d/s)**2 C13 * -0.0009 0.0021 - 0.416 0.173 C14 * 0.0004 0.0024 0.148 0.022 C15 * 0.0002 0.0024 0.092 0.008 C16 * 0.0000 0.0031 - 0.008 0.000 C17 * -0.0013 0.0032 - 0.417 0.174 C18 * 0.0015 0.0026 0.593 0.352 ============ Sum((d/s)**2) for starred atoms 0.729 Chi-squared at 95% for 3 degrees of freedom: 7.81 The group of atoms does not deviate significantly from planarity Dihedral angles formed by LSQ-planes Plane - plane angle (s.u.) angle (s.u.) 1 2 29.32 (0.08) 150.68 (0.08) 1 3 53.76 (0.09) 126.24 (0.09) 1 4 71.41 (0.08) 108.59 (0.08) 2 3 24.43 (0.06) 155.57 (0.06) 2 4 82.56 (0.07) 97.44 (0.07) 3 4 61.02 (0.09) 118.98 (0.09) |
x | y | z | Uiso*/Ueq | ||
H1B | 0.917 (2) | −0.0477 (16) | 0.155 (2) | 0.046 (6)* | |
H1A | 0.861 (3) | 0.0248 (16) | 0.254 (3) | 0.051 (7)* | |
H14 | 0.710 (3) | 0.1230 (16) | −0.039 (3) | 0.051 (7)* | |
H5B | 0.965 (3) | 0.1467 (16) | 0.409 (3) | 0.056 (7)* | |
H9 | 1.099 (3) | −0.1349 (19) | 0.253 (3) | 0.067 (8)* | |
H5A | 1.120 (3) | 0.1866 (18) | 0.449 (3) | 0.065 (8)* | |
H18 | 0.598 (3) | 0.2135 (17) | 0.316 (3) | 0.055 (7)* | |
H17 | 0.355 (4) | 0.188 (2) | 0.239 (3) | 0.083 (9)* | |
H7 | 1.395 (3) | −0.050 (2) | 0.542 (3) | 0.079 (9)* | |
H16 | 0.290 (3) | 0.1295 (19) | 0.021 (3) | 0.079 (9)* | |
H6 | 1.297 (3) | 0.092 (2) | 0.527 (3) | 0.077 (9)* | |
H8 | 1.300 (3) | −0.161 (2) | 0.409 (3) | 0.077 (9)* | |
P3 | 0.95300 (7) | 0.17206 (4) | 0.12972 (6) | 0.0471 (2) | |
O2 | 0.96005 (17) | 0.07175 (11) | 0.09953 (15) | 0.0488 (4) | |
O12 | 0.81116 (17) | 0.18791 (12) | 0.19813 (17) | 0.0552 (5) | |
O4 | 1.06595 (17) | 0.19351 (11) | 0.25298 (17) | 0.0525 (4) | |
C13 | 0.6713 (2) | 0.16995 (14) | 0.1437 (2) | 0.0441 (5) | |
C1 | 0.9425 (3) | 0.00625 (17) | 0.2053 (3) | 0.0514 (6) | |
C17 | 0.4295 (3) | 0.1753 (2) | 0.1840 (3) | 0.0688 (8) | |
C10 | 1.0741 (2) | −0.00767 (16) | 0.3010 (2) | 0.0464 (5) | |
C11 | 1.1328 (3) | 0.05989 (16) | 0.3860 (2) | 0.0477 (6) | |
C14 | 0.6366 (3) | 0.13571 (16) | 0.0140 (2) | 0.0475 (6) | |
C15 | 0.4945 (3) | 0.12077 (16) | −0.0322 (3) | 0.0533 (6) | |
C18 | 0.5687 (3) | 0.19024 (17) | 0.2296 (3) | 0.0531 (6) | |
O20 | 0.9707 (2) | 0.22364 (14) | 0.00823 (19) | 0.0765 (6) | |
C8 | 1.2552 (3) | −0.1063 (2) | 0.4018 (3) | 0.0685 (8) | |
C5 | 1.0656 (3) | 0.14842 (18) | 0.3860 (2) | 0.0551 (6) | |
C6 | 1.2536 (3) | 0.0427 (2) | 0.4751 (3) | 0.0608 (7) | |
C19 | 0.4540 (3) | 0.0842 (2) | −0.1749 (3) | 0.0731 (8) | |
H19A | 0.5385 | 0.0744 | −0.2199 | 0.110* | |
H19B | 0.3937 | 0.1255 | −0.2276 | 0.110* | |
H19C | 0.4041 | 0.0296 | −0.1680 | 0.110* | |
C9 | 1.1379 (3) | −0.08979 (18) | 0.3091 (3) | 0.0600 (7) | |
C7 | 1.3130 (3) | −0.0397 (2) | 0.4842 (3) | 0.0684 (8) | |
C16 | 0.3917 (3) | 0.1410 (2) | 0.0541 (3) | 0.0672 (8) |
U11 | U22 | U33 | U12 | U13 | U23 | |
P3 | 0.0502 (4) | 0.0520 (4) | 0.0390 (3) | −0.0056 (3) | 0.0042 (3) | 0.0021 (3) |
O2 | 0.0520 (9) | 0.0576 (10) | 0.0370 (8) | 0.0002 (7) | 0.0055 (7) | −0.0070 (7) |
O12 | 0.0523 (10) | 0.0660 (11) | 0.0464 (9) | 0.0069 (8) | 0.0005 (7) | −0.0126 (8) |
O4 | 0.0568 (10) | 0.0488 (10) | 0.0505 (10) | −0.0112 (8) | −0.0012 (8) | 0.0011 (7) |
C13 | 0.0484 (13) | 0.0395 (12) | 0.0439 (12) | 0.0061 (10) | 0.0020 (10) | 0.0054 (10) |
C1 | 0.0538 (15) | 0.0454 (14) | 0.0545 (15) | −0.0091 (11) | 0.0029 (12) | −0.0074 (12) |
C17 | 0.0589 (17) | 0.076 (2) | 0.075 (2) | 0.0094 (14) | 0.0236 (15) | 0.0025 (16) |
C10 | 0.0472 (13) | 0.0487 (14) | 0.0446 (13) | −0.0043 (10) | 0.0103 (10) | 0.0018 (10) |
C11 | 0.0524 (13) | 0.0537 (14) | 0.0373 (12) | −0.0054 (11) | 0.0057 (10) | 0.0005 (10) |
C14 | 0.0530 (14) | 0.0479 (14) | 0.0424 (13) | 0.0023 (11) | 0.0084 (11) | 0.0038 (10) |
C15 | 0.0569 (15) | 0.0486 (14) | 0.0532 (15) | −0.0074 (11) | −0.0004 (12) | 0.0108 (11) |
C18 | 0.0611 (16) | 0.0515 (15) | 0.0477 (14) | 0.0112 (12) | 0.0103 (12) | 0.0007 (12) |
O20 | 0.0871 (14) | 0.0877 (15) | 0.0541 (11) | −0.0194 (11) | 0.0038 (10) | 0.0230 (10) |
C8 | 0.0675 (18) | 0.0645 (19) | 0.075 (2) | 0.0135 (15) | 0.0169 (15) | 0.0169 (16) |
C5 | 0.0685 (18) | 0.0561 (15) | 0.0383 (13) | −0.0039 (13) | −0.0062 (12) | −0.0094 (11) |
C6 | 0.0611 (16) | 0.0717 (19) | 0.0477 (15) | −0.0093 (14) | −0.0039 (12) | 0.0070 (13) |
C19 | 0.0742 (19) | 0.083 (2) | 0.0588 (17) | −0.0238 (16) | −0.0082 (14) | 0.0035 (15) |
C9 | 0.0660 (17) | 0.0509 (15) | 0.0643 (17) | −0.0013 (13) | 0.0124 (14) | 0.0010 (13) |
C7 | 0.0531 (16) | 0.087 (2) | 0.0636 (18) | 0.0031 (15) | 0.0005 (14) | 0.0246 (16) |
C16 | 0.0479 (15) | 0.0731 (19) | 0.080 (2) | −0.0034 (13) | 0.0044 (14) | 0.0060 (16) |
P3—O20 | 1.4437 (19) | C14—C15 | 1.390 (3) |
P3—O2 | 1.5556 (18) | C14—H14 | 0.93 (2) |
P3—O4 | 1.5583 (16) | C15—C16 | 1.381 (4) |
P3—O12 | 1.5735 (18) | C15—C19 | 1.511 (4) |
O2—C1 | 1.454 (3) | C18—H18 | 0.93 (3) |
O12—C13 | 1.400 (3) | C8—C7 | 1.370 (5) |
O4—C5 | 1.467 (3) | C8—C9 | 1.380 (4) |
C13—C14 | 1.376 (3) | C8—H8 | 0.94 (3) |
C13—C18 | 1.377 (3) | C5—H5B | 1.00 (3) |
C1—C10 | 1.493 (3) | C5—H5A | 0.96 (3) |
C1—H1B | 0.97 (2) | C6—C7 | 1.373 (4) |
C1—H1A | 0.99 (3) | C6—H6 | 0.96 (3) |
C17—C18 | 1.363 (4) | C19—H19A | 0.9600 |
C17—C16 | 1.383 (4) | C19—H19B | 0.9600 |
C17—H17 | 0.94 (3) | C19—H19C | 0.9600 |
C10—C9 | 1.385 (4) | C9—H9 | 0.93 (3) |
C10—C11 | 1.398 (3) | C7—H7 | 0.93 (3) |
C11—C6 | 1.386 (4) | C16—H16 | 1.00 (3) |
C11—C5 | 1.488 (4) | ||
O20—P3—O2 | 111.51 (11) | C14—C15—C19 | 120.3 (2) |
O20—P3—O4 | 113.07 (11) | C17—C18—C13 | 118.6 (3) |
O2—P3—O4 | 108.18 (9) | C17—C18—H18 | 123.1 (15) |
O20—P3—O12 | 115.96 (12) | C13—C18—H18 | 118.3 (16) |
O2—P3—O12 | 106.55 (9) | C7—C8—C9 | 119.7 (3) |
O4—P3—O12 | 100.76 (9) | C7—C8—H8 | 117.5 (18) |
C1—O2—P3 | 121.80 (15) | C9—C8—H8 | 122.8 (19) |
C13—O12—P3 | 128.33 (15) | O4—C5—C11 | 112.6 (2) |
C5—O4—P3 | 121.42 (15) | O4—C5—H5B | 107.5 (14) |
C14—C13—C18 | 121.8 (2) | C11—C5—H5B | 113.1 (15) |
C14—C13—O12 | 123.4 (2) | O4—C5—H5A | 103.6 (16) |
C18—C13—O12 | 114.8 (2) | C11—C5—H5A | 110.3 (16) |
O2—C1—C10 | 113.13 (19) | H5B—C5—H5A | 109 (2) |
O2—C1—H1B | 105.2 (14) | C7—C6—C11 | 121.2 (3) |
C10—C1—H1B | 109.9 (14) | C7—C6—H6 | 121.3 (17) |
O2—C1—H1A | 107.2 (14) | C11—C6—H6 | 117.5 (18) |
C10—C1—H1A | 112.5 (14) | C15—C19—H19A | 109.5 |
H1B—C1—H1A | 108.5 (19) | C15—C19—H19B | 109.5 |
C18—C17—C16 | 120.8 (3) | H19A—C19—H19B | 109.5 |
C18—C17—H17 | 121.9 (19) | C15—C19—H19C | 109.5 |
C16—C17—H17 | 117.3 (19) | H19A—C19—H19C | 109.5 |
C9—C10—C11 | 119.0 (2) | H19B—C19—H19C | 109.5 |
C9—C10—C1 | 119.6 (2) | C8—C9—C10 | 121.1 (3) |
C11—C10—C1 | 121.4 (2) | C8—C9—H9 | 119.5 (18) |
C6—C11—C10 | 119.0 (2) | C10—C9—H9 | 119.4 (18) |
C6—C11—C5 | 119.6 (2) | C8—C7—C6 | 120.0 (3) |
C10—C11—C5 | 121.4 (2) | C8—C7—H7 | 119.2 (19) |
C13—C14—C15 | 119.5 (2) | C6—C7—H7 | 120.7 (19) |
C13—C14—H14 | 117.9 (15) | C15—C16—C17 | 120.6 (3) |
C15—C14—H14 | 122.6 (15) | C15—C16—H16 | 118.5 (18) |
C16—C15—C14 | 118.7 (2) | C17—C16—H16 | 120.9 (18) |
C16—C15—C19 | 121.0 (3) | ||
O20—P3—O2—C1 | −178.85 (17) | O12—C13—C14—C15 | −179.4 (2) |
O4—P3—O2—C1 | 56.20 (19) | C13—C14—C15—C16 | 0.1 (4) |
O12—P3—O2—C1 | −51.41 (18) | C13—C14—C15—C19 | 179.3 (2) |
O20—P3—O12—C13 | 65.4 (2) | C16—C17—C18—C13 | −0.3 (4) |
O2—P3—O12—C13 | −59.4 (2) | C14—C13—C18—C17 | 0.3 (4) |
O4—P3—O12—C13 | −172.21 (18) | O12—C13—C18—C17 | 179.6 (2) |
O20—P3—O4—C5 | 179.67 (19) | P3—O4—C5—C11 | 80.4 (3) |
O2—P3—O4—C5 | −56.3 (2) | C6—C11—C5—O4 | 118.0 (2) |
O12—P3—O4—C5 | 55.2 (2) | C10—C11—C5—O4 | −64.1 (3) |
P3—O12—C13—C14 | −1.6 (3) | C10—C11—C6—C7 | −2.2 (4) |
P3—O12—C13—C18 | 179.22 (17) | C5—C11—C6—C7 | 175.8 (3) |
P3—O2—C1—C10 | −79.9 (2) | C7—C8—C9—C10 | −2.3 (4) |
O2—C1—C10—C9 | −118.7 (2) | C11—C10—C9—C8 | 1.8 (4) |
O2—C1—C10—C11 | 63.1 (3) | C1—C10—C9—C8 | −176.5 (2) |
C9—C10—C11—C6 | 0.4 (3) | C9—C8—C7—C6 | 0.5 (4) |
C1—C10—C11—C6 | 178.7 (2) | C11—C6—C7—C8 | 1.8 (4) |
C9—C10—C11—C5 | −177.5 (2) | C14—C15—C16—C17 | −0.1 (4) |
C1—C10—C11—C5 | 0.7 (4) | C19—C15—C16—C17 | −179.3 (3) |
C18—C13—C14—C15 | −0.2 (4) | C18—C17—C16—C15 | 0.2 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···O12 | 0.99 (3) | 2.57 (2) | 3.025 (3) | 108.0 (18) |
C5—H5B···O12 | 1.00 (3) | 2.48 (3) | 2.932 (3) | 106.8 (19) |
C18—H18···O20i | 0.93 (3) | 2.51 (3) | 3.233 (3) | 134 (2) |
Symmetry code: (i) x−1/2, −y+1/2, z+1/2. |
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