Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021982/hb2080sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021982/hb2080Isup2.hkl |
CCDC reference: 614866
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO & SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2003).
C12H17OP | F(000) = 448 |
Mr = 208.23 | Dx = 1.159 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 9543 reflections |
a = 6.0852 (4) Å | θ = 3.0–25.4° |
b = 7.3750 (6) Å | µ = 0.20 mm−1 |
c = 26.598 (2) Å | T = 291 K |
V = 1193.67 (15) Å3 | Column, colourless |
Z = 4 | 0.28 × 0.10 × 0.06 mm |
Nonius KappaCCD diffractometer | 1367 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.046 |
Graphite monochromator | θmax = 25.4°, θmin = 3.1° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −7→7 |
ω scans | k = −8→8 |
9543 measured reflections | l = −31→32 |
2179 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H-atom parameters constrained |
wR(F2) = 0.049 | w = 1/[σ2(Fo2)] |
S = 0.82 | (Δ/σ)max < 0.001 |
2179 reflections | Δρmax = 0.21 e Å−3 |
130 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 862 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.10 (8) |
Experimental. 403 frames via ω-rotation (Δω = 1°) and two times 80 s per frame (four sets at different κ-angles). |
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 | −0.21240 (8) | −0.01471 (7) | −0.093663 (19) | 0.04939 (16) | |
O1 | 0.02732 (17) | 0.01059 (17) | −0.08598 (4) | 0.0613 (4) | |
C1 | −0.3090 (4) | 0.1088 (2) | −0.14826 (8) | 0.0477 (6) | |
C2 | −0.5182 (4) | 0.1824 (3) | −0.15283 (8) | 0.0583 (6) | |
H2A | −0.6215 | 0.1634 | −0.1276 | 0.070* | |
C3 | −0.5737 (4) | 0.2838 (3) | −0.19467 (9) | 0.0701 (7) | |
H3A | −0.7135 | 0.3340 | −0.1972 | 0.084* | |
C4 | −0.4235 (5) | 0.3108 (3) | −0.23257 (9) | 0.0765 (7) | |
H4A | −0.4613 | 0.3793 | −0.2606 | 0.092* | |
C5 | −0.2188 (4) | 0.2369 (3) | −0.22884 (9) | 0.0762 (7) | |
H5A | −0.1180 | 0.2527 | −0.2547 | 0.091* | |
C6 | −0.1608 (3) | 0.1382 (3) | −0.18657 (9) | 0.0645 (7) | |
H6A | −0.0195 | 0.0911 | −0.1840 | 0.077* | |
C11 | −0.2866 (3) | −0.2520 (2) | −0.10271 (7) | 0.0504 (5) | |
C12 | −0.2141 (3) | −0.3561 (2) | −0.05535 (8) | 0.0811 (7) | |
H12A | −0.2376 | −0.4836 | −0.0603 | 0.122* | |
H12B | −0.2984 | −0.3155 | −0.0270 | 0.122* | |
H12C | −0.0609 | −0.3342 | −0.0492 | 0.122* | |
C13 | −0.5360 (3) | −0.2771 (2) | −0.11053 (8) | 0.0691 (7) | |
H13A | −0.5688 | −0.4039 | −0.1137 | 0.104* | |
H13B | −0.5807 | −0.2149 | −0.1405 | 0.104* | |
H13C | −0.6137 | −0.2282 | −0.0822 | 0.104* | |
C14 | −0.1623 (3) | −0.3259 (3) | −0.14825 (8) | 0.0749 (7) | |
H14A | −0.1899 | −0.4536 | −0.1514 | 0.112* | |
H14B | −0.0076 | −0.3059 | −0.1438 | 0.112* | |
H14C | −0.2113 | −0.2648 | −0.1781 | 0.112* | |
C21 | −0.3712 (3) | 0.0638 (2) | −0.04198 (8) | 0.0527 (6) | |
H21A | −0.5234 | 0.0701 | −0.0447 | 0.063* | |
C22 | −0.2745 (4) | 0.1130 (2) | −0.00008 (8) | 0.0698 (7) | |
H22B | −0.1223 | 0.1069 | 0.0027 | 0.084* | |
H22C | −0.3581 | 0.1540 | 0.0269 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0429 (3) | 0.0540 (3) | 0.0512 (3) | −0.0007 (3) | 0.0022 (3) | −0.0027 (3) |
O1 | 0.0392 (8) | 0.0729 (9) | 0.0719 (10) | −0.0050 (8) | −0.0029 (6) | −0.0033 (9) |
C1 | 0.0497 (15) | 0.0457 (12) | 0.0477 (15) | −0.0068 (12) | 0.0061 (12) | −0.0001 (10) |
C2 | 0.0549 (17) | 0.0599 (14) | 0.0600 (17) | −0.0003 (13) | 0.0024 (13) | 0.0051 (13) |
C3 | 0.0679 (18) | 0.0657 (16) | 0.0766 (19) | −0.0013 (15) | −0.0169 (17) | 0.0103 (15) |
C4 | 0.101 (2) | 0.0690 (17) | 0.0601 (19) | −0.0174 (18) | −0.0171 (19) | 0.0109 (14) |
C5 | 0.089 (2) | 0.0836 (19) | 0.0559 (17) | −0.0110 (17) | 0.0135 (16) | 0.0111 (14) |
C6 | 0.0645 (19) | 0.0681 (17) | 0.0609 (17) | −0.0055 (12) | 0.0062 (14) | 0.0002 (14) |
C11 | 0.0443 (12) | 0.0501 (12) | 0.0567 (14) | 0.0017 (11) | −0.0008 (13) | −0.0006 (12) |
C12 | 0.1008 (19) | 0.0564 (14) | 0.0861 (18) | 0.0050 (15) | −0.0150 (16) | 0.0108 (13) |
C13 | 0.0540 (15) | 0.0600 (14) | 0.0934 (19) | −0.0100 (12) | 0.0053 (13) | −0.0073 (13) |
C14 | 0.0680 (18) | 0.0686 (15) | 0.0882 (19) | 0.0051 (13) | 0.0037 (13) | −0.0214 (13) |
C21 | 0.0497 (13) | 0.0582 (14) | 0.0501 (15) | −0.0002 (10) | 0.0019 (11) | −0.0026 (11) |
C22 | 0.0717 (17) | 0.0747 (16) | 0.0631 (16) | −0.0051 (14) | 0.0037 (16) | −0.0085 (12) |
P1—O1 | 1.4847 (11) | C11—C12 | 1.540 (2) |
P1—C21 | 1.7772 (19) | C11—C13 | 1.543 (2) |
P1—C1 | 1.812 (2) | C12—H12A | 0.9600 |
P1—C11 | 1.8232 (18) | C12—H12B | 0.9600 |
C1—C6 | 1.378 (3) | C12—H12C | 0.9600 |
C1—C2 | 1.389 (2) | C13—H13A | 0.9600 |
C2—C3 | 1.383 (2) | C13—H13B | 0.9600 |
C2—H2A | 0.9300 | C13—H13C | 0.9600 |
C3—C4 | 1.376 (3) | C14—H14A | 0.9600 |
C3—H3A | 0.9300 | C14—H14B | 0.9600 |
C4—C5 | 1.363 (3) | C14—H14C | 0.9600 |
C4—H4A | 0.9300 | C21—C22 | 1.311 (2) |
C5—C6 | 1.385 (3) | C21—H21A | 0.9300 |
C5—H5A | 0.9300 | C22—H22B | 0.9300 |
C6—H6A | 0.9300 | C22—H22C | 0.9300 |
C11—C14 | 1.529 (2) | ||
O1—P1—C21 | 112.75 (9) | C14—C11—P1 | 108.93 (14) |
O1—P1—C1 | 111.46 (9) | C12—C11—P1 | 107.43 (13) |
C21—P1—C1 | 106.24 (9) | C13—C11—P1 | 112.13 (12) |
O1—P1—C11 | 112.46 (9) | C11—C12—H12A | 109.5 |
C21—P1—C11 | 106.27 (9) | C11—C12—H12B | 109.5 |
C1—P1—C11 | 107.23 (9) | H12A—C12—H12B | 109.5 |
C6—C1—C2 | 118.24 (19) | C11—C12—H12C | 109.5 |
C6—C1—P1 | 117.35 (18) | H12A—C12—H12C | 109.5 |
C2—C1—P1 | 124.33 (18) | H12B—C12—H12C | 109.5 |
C3—C2—C1 | 120.4 (2) | C11—C13—H13A | 109.5 |
C3—C2—H2A | 119.8 | C11—C13—H13B | 109.5 |
C1—C2—H2A | 119.8 | H13A—C13—H13B | 109.5 |
C4—C3—C2 | 120.4 (2) | C11—C13—H13C | 109.5 |
C4—C3—H3A | 119.8 | H13A—C13—H13C | 109.5 |
C2—C3—H3A | 119.8 | H13B—C13—H13C | 109.5 |
C5—C4—C3 | 119.7 (2) | C11—C14—H14A | 109.5 |
C5—C4—H4A | 120.1 | C11—C14—H14B | 109.5 |
C3—C4—H4A | 120.1 | H14A—C14—H14B | 109.5 |
C4—C5—C6 | 120.1 (2) | C11—C14—H14C | 109.5 |
C4—C5—H5A | 119.9 | H14A—C14—H14C | 109.5 |
C6—C5—H5A | 119.9 | H14B—C14—H14C | 109.5 |
C1—C6—C5 | 121.1 (2) | C22—C21—P1 | 120.24 (17) |
C1—C6—H6A | 119.5 | C22—C21—H21A | 119.9 |
C5—C6—H6A | 119.5 | P1—C21—H21A | 119.9 |
C14—C11—C12 | 109.18 (16) | C21—C22—H22B | 120.0 |
C14—C11—C13 | 109.70 (17) | C21—C22—H22C | 120.0 |
C12—C11—C13 | 109.41 (16) | H22B—C22—H22C | 120.0 |
O1—P1—C1—C6 | 28.1 (2) | C4—C5—C6—C1 | 1.7 (3) |
C21—P1—C1—C6 | 151.29 (16) | O1—P1—C11—C14 | −58.53 (16) |
C11—P1—C1—C6 | −95.39 (17) | C21—P1—C11—C14 | 177.64 (14) |
O1—P1—C1—C2 | −148.71 (16) | C1—P1—C11—C14 | 64.34 (17) |
C21—P1—C1—C2 | −25.5 (2) | O1—P1—C11—C12 | 59.61 (16) |
C11—P1—C1—C2 | 87.80 (19) | C21—P1—C11—C12 | −64.22 (16) |
C6—C1—C2—C3 | −0.6 (3) | C1—P1—C11—C12 | −177.52 (14) |
P1—C1—C2—C3 | 176.19 (16) | O1—P1—C11—C13 | 179.86 (13) |
C1—C2—C3—C4 | 0.9 (3) | C21—P1—C11—C13 | 56.03 (17) |
C2—C3—C4—C5 | 0.1 (3) | C1—P1—C11—C13 | −57.27 (17) |
C3—C4—C5—C6 | −1.4 (4) | O1—P1—C21—C22 | −8.9 (2) |
C2—C1—C6—C5 | −0.7 (3) | C1—P1—C21—C22 | −131.24 (17) |
P1—C1—C6—C5 | −177.69 (15) | C11—P1—C21—C22 | 114.78 (17) |