Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803012169/fl6040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803012169/fl6040Isup2.hkl |
CCDC reference: 217445
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.007 Å
- R factor = 0.038
- wR factor = 0.039
- Data-to-parameter ratio = 7.4
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFNR_01 Alert C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5882 Proportion of unique data used 0.5388 Ratio reflections to parameters 7.4481 THETM_01 Alert C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5882 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 24.71 From the CIF: _reflns_number_total 5861 Count of symmetry unique reflns 3456 Completeness (_total/calc) 169.59% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 2405 Fraction of Friedel pairs measured 0.696 Are heavy atom types Z>Si present yes 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
The title compound was prepared by the stepwise reaction of (+)-menthol and (-)-TADDOL with phosphorous trichloride according to a literature procedure (Alexakis et al., 2000). X-ray quality crystals were obtained by slowly cooling a concentrated solution of the title compound in an ether/pentane mixture to 238 K.
Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare, 1993); program(s) used to refine structure: TEXSAN (Molecular Structure Corporation, 1985, 1992); molecular graphics: please provide; software used to prepare material for publication: TEXSAN.
Fig. 1. The title compound, with displacement parameters drawn at the 50% probability level. Hydrogen atoms are omitted for clarity. |
C41H47O5P | Dx = 1.209 Mg m−3 |
Mr = 650.79 | Mo Kα radiation, λ = 0.7107 Å |
Orthorhombic, P212121 | Cell parameters from 4403 reflections |
a = 17.884 (1) Å | θ = 2.3–22.4° |
b = 8.9233 (6) Å | µ = 0.12 mm−1 |
c = 22.395 (2) Å | T = 133 K |
V = 3574.0 (4) Å3 | Column, colorless |
Z = 4 | 0.27 × 0.20 × 0.09 mm |
F(000) = 1392.00 |
SMART 1K CCD diffractometer | 5861 independent reflections |
Radiation source: X-ray tube | 3158 reflections with I > 3.00σ(I) |
Graphite monochromator | Rint = 0.069 |
ω–scan | θmax = 24.7° |
Absorption correction: multi-scan (Blessing, 1995) | h = −21→20 |
Tmin = 0.967, Tmax = 0.989 | k = −9→10 |
15797 measured reflections | l = −22→26 |
Refinement on F | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.038 | Weighting scheme based on measured s.u.'s Please provide expression for w |
wR(F2) = 0.039 | (Δ/σ)max = 0.001 |
S = 0.96 | Δρmax = 0.21 e Å−3 |
3158 reflections | Δρmin = −0.32 e Å−3 |
424 parameters |
C41H47O5P | V = 3574.0 (4) Å3 |
Mr = 650.79 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 17.884 (1) Å | µ = 0.12 mm−1 |
b = 8.9233 (6) Å | T = 133 K |
c = 22.395 (2) Å | 0.27 × 0.20 × 0.09 mm |
SMART 1K CCD diffractometer | 5861 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 3158 reflections with I > 3.00σ(I) |
Tmin = 0.967, Tmax = 0.989 | Rint = 0.069 |
15797 measured reflections |
R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
wR(F2) = 0.039 | H-atom parameters constrained |
S = 0.96 | Δρmax = 0.21 e Å−3 |
3158 reflections | Δρmin = −0.32 e Å−3 |
424 parameters |
x | y | z | Uiso*/Ueq | ||
P(1) | 0.10922 (6) | 0.2157 (1) | 1.01543 (5) | 0.0188 | |
O(1) | 0.0815 (2) | 0.1010 (3) | 1.0663 (1) | 0.0200 | |
O(2) | 0.0284 (1) | 0.2191 (3) | 0.9818 (1) | 0.0174 | |
O(3) | 0.1526 (2) | 0.0885 (3) | 0.9742 (1) | 0.0191 | |
O(4) | 0.0662 (2) | 0.3920 (3) | 0.8362 (1) | 0.0212 | |
O(5) | 0.1294 (2) | 0.1764 (3) | 0.8153 (1) | 0.0165 | |
C(1) | 0.1229 (2) | 0.0993 (5) | 1.1230 (2) | 0.0222 | |
C(2) | 0.0861 (3) | 0.2122 (6) | 1.1649 (2) | 0.0279 | |
C(3) | 0.1189 (2) | 0.2075 (6) | 1.2281 (2) | 0.0294 | |
C(4) | 0.1150 (3) | 0.0470 (5) | 1.2521 (2) | 0.0289 | |
C(5) | 0.1534 (3) | −0.0649 (5) | 1.2096 (2) | 0.0333 | |
C(6) | 0.1201 (3) | −0.0611 (5) | 1.1464 (2) | 0.0250 | |
C(7) | 0.0806 (3) | 0.3172 (6) | 1.2691 (2) | 0.0397 | |
C(8) | 0.1559 (3) | −0.1768 (5) | 1.1042 (2) | 0.0338 | |
C(9) | 0.1370 (3) | −0.3383 (6) | 1.1222 (2) | 0.0535 | |
C(10) | 0.2395 (3) | −0.1583 (6) | 1.0965 (2) | 0.0396 | |
C(11) | 0.0141 (2) | 0.3283 (4) | 0.9346 (2) | 0.0188 | |
C(12) | 0.0027 (2) | 0.4834 (5) | 0.9636 (2) | 0.0215 | |
C(13) | −0.0421 (3) | 0.4938 (5) | 1.0149 (2) | 0.0310 | |
C(14) | −0.0538 (3) | 0.6310 (6) | 1.0419 (2) | 0.0329 | |
C(15) | −0.0211 (3) | 0.7602 (5) | 1.0188 (2) | 0.0315 | |
C(16) | 0.0235 (3) | 0.7497 (5) | 0.9689 (2) | 0.0343 | |
C(17) | 0.0351 (3) | 0.6118 (5) | 0.9409 (2) | 0.0219 | |
C(18) | −0.0576 (2) | 0.2759 (5) | 0.9045 (2) | 0.0186 | |
C(19) | −0.0989 (3) | 0.3727 (5) | 0.8693 (2) | 0.0351 | |
C(20) | −0.1641 (3) | 0.3242 (6) | 0.8407 (2) | 0.0322 | |
C(21) | −0.1874 (3) | 0.1792 (6) | 0.8483 (2) | 0.0388 | |
C(22) | −0.1483 (3) | 0.0817 (6) | 0.8831 (2) | 0.0335 | |
C(23) | −0.0827 (3) | 0.1281 (5) | 0.9105 (2) | 0.0197 | |
C(24) | 0.0820 (2) | 0.3231 (4) | 0.8926 (2) | 0.0134 | |
C(25) | 0.1084 (2) | 0.1629 (4) | 0.8774 (2) | 0.0180 | |
C(26) | 0.0845 (3) | 0.2900 (5) | 0.7883 (2) | 0.0215 | |
C(27) | 0.0144 (3) | 0.2237 (6) | 0.7618 (2) | 0.0350 | |
C(28) | 0.1330 (3) | 0.3708 (5) | 0.7435 (2) | 0.0326 | |
C(29) | 0.1760 (2) | 0.1048 (5) | 0.9118 (2) | 0.0172 | |
C(30) | 0.1946 (2) | −0.0586 (5) | 0.8944 (2) | 0.0201 | |
C(31) | 0.1648 (3) | −0.1310 (5) | 0.8449 (2) | 0.0260 | |
C(32) | 0.1844 (3) | −0.2791 (5) | 0.8323 (2) | 0.0257 | |
C(33) | 0.2329 (3) | −0.3540 (5) | 0.8676 (2) | 0.0274 | |
C(34) | 0.2635 (3) | −0.2828 (5) | 0.9171 (2) | 0.0339 | |
C(35) | 0.2454 (3) | −0.1352 (5) | 0.9293 (2) | 0.0224 | |
C(36) | 0.2461 (2) | 0.1998 (5) | 0.9068 (2) | 0.0187 | |
C(37) | 0.2764 (3) | 0.2799 (5) | 0.9548 (2) | 0.0222 | |
C(38) | 0.3421 (3) | 0.3609 (5) | 0.9486 (2) | 0.0280 | |
C(39) | 0.3786 (2) | 0.3657 (5) | 0.8949 (2) | 0.0256 | |
C(40) | 0.3499 (3) | 0.2883 (6) | 0.8471 (2) | 0.0363 | |
C(41) | 0.2846 (3) | 0.2066 (5) | 0.8525 (2) | 0.0210 | |
H(1) | 0.1733 | 0.1275 | 1.1161 | 0.0266* | |
H(2) | 0.0929 | 0.3099 | 1.1490 | 0.0335* | |
H(3) | 0.0341 | 0.1905 | 1.1672 | 0.0335* | |
H(4) | 0.1702 | 0.2350 | 1.2256 | 0.0353* | |
H(5) | 0.1390 | 0.0432 | 1.2899 | 0.0346* | |
H(6) | 0.0640 | 0.0193 | 1.2565 | 0.0346* | |
H(7) | 0.2051 | −0.0408 | 1.2072 | 0.0400* | |
H(8) | 0.1478 | −0.1632 | 1.2253 | 0.0400* | |
H(9) | 0.0688 | −0.0872 | 1.1500 | 0.0300* | |
H(10) | 0.1024 | 0.3117 | 1.3077 | 0.0477* | |
H(11) | 0.0862 | 0.4159 | 1.2537 | 0.0477* | |
H(12) | 0.0289 | 0.2933 | 1.2716 | 0.0477* | |
H(13) | 0.1342 | −0.1612 | 1.0660 | 0.0405* | |
H(14) | 0.0844 | −0.3482 | 1.1267 | 0.0642* | |
H(15) | 0.1541 | −0.4052 | 1.0923 | 0.0642* | |
H(16) | 0.1608 | −0.3612 | 1.1591 | 0.0642* | |
H(17) | 0.2639 | −0.1807 | 1.1331 | 0.0475* | |
H(18) | 0.2568 | −0.2246 | 1.0663 | 0.0475* | |
H(19) | 0.2503 | −0.0579 | 1.0853 | 0.0475* | |
H(20) | −0.0645 | 0.4063 | 1.0310 | 0.0371* | |
H(21) | −0.0843 | 0.6371 | 1.0766 | 0.0395* | |
H(22) | −0.0296 | 0.8546 | 1.0373 | 0.0377* | |
H(23) | 0.0466 | 0.8372 | 0.9532 | 0.0412* | |
H(24) | 0.0655 | 0.6064 | 0.9062 | 0.0262* | |
H(25) | −0.0828 | 0.4734 | 0.8645 | 0.0421* | |
H(26) | −0.1920 | 0.3910 | 0.8163 | 0.0387* | |
H(27) | −0.2317 | 0.1461 | 0.8289 | 0.0465* | |
H(28) | −0.1659 | −0.0179 | 0.8885 | 0.0402* | |
H(29) | −0.0546 | 0.0590 | 0.9336 | 0.0237* | |
H(30) | 0.1222 | 0.3754 | 0.9109 | 0.0160* | |
H(31) | 0.0680 | 0.0947 | 0.8814 | 0.0217* | |
H(32) | −0.0148 | 0.3011 | 0.7443 | 0.0420* | |
H(33) | 0.0274 | 0.1523 | 0.7322 | 0.0420* | |
H(34) | −0.0137 | 0.1760 | 0.7924 | 0.0420* | |
H(35) | 0.1749 | 0.4134 | 0.7633 | 0.0391* | |
H(36) | 0.1498 | 0.3018 | 0.7141 | 0.0391* | |
H(37) | 0.1048 | 0.4479 | 0.7249 | 0.0391* | |
H(38) | 0.1309 | −0.0795 | 0.8195 | 0.0312* | |
H(39) | 0.1635 | −0.3278 | 0.7985 | 0.0309* | |
H(40) | 0.2460 | −0.4546 | 0.8587 | 0.0329* | |
H(41) | 0.2969 | −0.3355 | 0.9425 | 0.0407* | |
H(42) | 0.2682 | −0.0860 | 0.9622 | 0.0268* | |
H(43) | 0.2515 | 0.2788 | 0.9923 | 0.0266* | |
H(44) | 0.3619 | 0.4136 | 0.9818 | 0.0337* | |
H(45) | 0.4234 | 0.4219 | 0.8908 | 0.0308* | |
H(46) | 0.3752 | 0.2910 | 0.8098 | 0.0436* | |
H(47) | 0.2656 | 0.1544 | 0.8188 | 0.0252* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P(1) | 0.0222 (7) | 0.0154 (7) | 0.0141 (6) | 0.0020 (7) | 0.0010 (6) | 0.0009 (6) |
O(1) | 0.029 (2) | 0.024 (2) | 0.009 (1) | 0.002 (2) | −0.002 (1) | 0.007 (1) |
O(2) | 0.017 (2) | 0.018 (2) | 0.012 (1) | 0.001 (1) | 0.000 (1) | 0.003 (1) |
O(3) | 0.025 (2) | 0.017 (2) | 0.014 (2) | 0.004 (1) | 0.005 (1) | 0.000 (1) |
O(4) | 0.038 (2) | 0.012 (2) | 0.011 (2) | 0.006 (2) | 0.002 (1) | 0.003 (1) |
O(5) | 0.028 (2) | 0.020 (2) | 0.011 (1) | 0.007 (1) | 0.003 (1) | 0.002 (1) |
C(1) | 0.025 (3) | 0.025 (3) | 0.015 (2) | −0.006 (2) | −0.005 (2) | 0.001 (2) |
C(2) | 0.029 (3) | 0.032 (3) | 0.021 (2) | −0.004 (3) | −0.001 (2) | 0.004 (2) |
C(3) | 0.030 (3) | 0.030 (3) | 0.017 (2) | −0.002 (3) | 0.000 (2) | 0.002 (2) |
C(4) | 0.036 (3) | 0.041 (3) | 0.018 (3) | 0.001 (3) | 0.000 (3) | 0.007 (2) |
C(5) | 0.042 (3) | 0.036 (3) | 0.017 (2) | −0.001 (3) | −0.002 (2) | 0.012 (2) |
C(6) | 0.024 (3) | 0.029 (3) | 0.019 (3) | −0.002 (2) | −0.002 (2) | 0.004 (2) |
C(7) | 0.053 (4) | 0.056 (4) | 0.021 (3) | 0.011 (3) | −0.002 (3) | −0.008 (3) |
C(8) | 0.044 (4) | 0.022 (3) | 0.028 (3) | 0.002 (3) | −0.011 (3) | 0.003 (2) |
C(9) | 0.095 (5) | 0.022 (3) | 0.049 (3) | 0.001 (3) | −0.013 (4) | 0.002 (3) |
C(10) | 0.053 (4) | 0.038 (3) | 0.032 (3) | 0.016 (3) | −0.004 (3) | −0.009 (2) |
C(11) | 0.021 (3) | 0.015 (3) | 0.011 (2) | 0.004 (2) | 0.007 (2) | 0.005 (2) |
C(12) | 0.021 (3) | 0.017 (3) | 0.023 (3) | 0.003 (2) | 0.001 (2) | 0.000 (2) |
C(13) | 0.029 (3) | 0.026 (3) | 0.026 (3) | 0.002 (2) | 0.006 (3) | −0.005 (2) |
C(14) | 0.031 (3) | 0.038 (3) | 0.034 (3) | 0.002 (3) | 0.009 (2) | −0.013 (3) |
C(15) | 0.033 (3) | 0.024 (3) | 0.039 (3) | 0.004 (2) | 0.002 (3) | −0.014 (3) |
C(16) | 0.034 (3) | 0.024 (3) | 0.041 (3) | −0.002 (2) | 0.004 (3) | 0.001 (2) |
C(17) | 0.028 (3) | 0.020 (3) | 0.027 (2) | 0.007 (2) | 0.008 (2) | −0.002 (2) |
C(18) | 0.020 (3) | 0.029 (3) | 0.008 (2) | 0.005 (3) | 0.003 (2) | −0.003 (2) |
C(19) | 0.027 (3) | 0.028 (3) | 0.026 (2) | 0.011 (3) | −0.003 (3) | 0.000 (2) |
C(20) | 0.026 (3) | 0.039 (4) | 0.033 (3) | 0.014 (3) | −0.010 (3) | −0.006 (2) |
C(21) | 0.033 (3) | 0.050 (4) | 0.031 (3) | 0.000 (3) | −0.009 (3) | −0.018 (3) |
C(22) | 0.026 (3) | 0.038 (3) | 0.026 (3) | −0.005 (3) | 0.001 (3) | −0.016 (2) |
C(23) | 0.026 (3) | 0.022 (3) | 0.015 (2) | 0.005 (2) | 0.006 (2) | 0.001 (2) |
C(24) | 0.020 (3) | 0.014 (3) | 0.013 (2) | 0.001 (2) | 0.002 (2) | 0.001 (2) |
C(25) | 0.017 (2) | 0.020 (3) | 0.015 (2) | 0.001 (2) | 0.006 (2) | 0.001 (2) |
C(26) | 0.033 (3) | 0.018 (2) | 0.018 (2) | 0.003 (3) | 0.003 (2) | 0.000 (2) |
C(27) | 0.044 (3) | 0.035 (3) | 0.024 (3) | 0.008 (3) | −0.009 (2) | −0.008 (2) |
C(28) | 0.062 (4) | 0.025 (3) | 0.017 (2) | 0.004 (3) | 0.011 (3) | 0.000 (2) |
C(29) | 0.015 (3) | 0.018 (3) | 0.015 (2) | −0.003 (2) | 0.000 (2) | 0.001 (2) |
C(30) | 0.028 (3) | 0.006 (2) | 0.018 (3) | 0.001 (2) | 0.005 (2) | 0.003 (2) |
C(31) | 0.029 (3) | 0.018 (3) | 0.021 (2) | 0.001 (2) | −0.008 (2) | 0.001 (2) |
C(32) | 0.039 (3) | 0.013 (3) | 0.025 (2) | 0.003 (3) | −0.003 (3) | −0.006 (2) |
C(33) | 0.034 (3) | 0.012 (3) | 0.032 (3) | 0.002 (2) | 0.004 (3) | −0.005 (2) |
C(34) | 0.049 (4) | 0.020 (3) | 0.042 (3) | 0.015 (3) | −0.013 (3) | 0.001 (3) |
C(35) | 0.035 (3) | 0.018 (3) | 0.029 (3) | 0.010 (3) | −0.010 (2) | −0.006 (2) |
C(36) | 0.017 (3) | 0.011 (2) | 0.021 (2) | 0.008 (2) | 0.001 (2) | 0.001 (2) |
C(37) | 0.026 (3) | 0.024 (3) | 0.012 (2) | 0.002 (3) | −0.001 (2) | 0.005 (2) |
C(38) | 0.028 (3) | 0.021 (3) | 0.018 (3) | −0.001 (3) | −0.006 (2) | 0.005 (2) |
C(39) | 0.019 (3) | 0.026 (3) | 0.030 (3) | 0.000 (3) | 0.003 (2) | −0.003 (2) |
C(40) | 0.030 (3) | 0.029 (3) | 0.027 (3) | 0.000 (3) | 0.008 (2) | −0.008 (3) |
C(41) | 0.025 (3) | 0.031 (3) | 0.017 (2) | −0.006 (3) | 0.003 (2) | −0.005 (2) |
P1—O1 | 1.610 (3) | C38—C39 | 1.368 (5) |
P1—O2 | 1.629 (3) | C39—C40 | 1.375 (6) |
P1—O3 | 1.656 (3) | C40—C41 | 1.381 (6) |
O1—C1 | 1.469 (5) | C1—H1 | 0.9500 |
O2—C11 | 1.460 (4) | C2—H2 | 0.9500 |
O3—C29 | 1.466 (4) | C2—H3 | 0.9500 |
O4—C24 | 1.434 (4) | C3—H4 | 0.9500 |
O4—C26 | 1.445 (5) | C4—H5 | 0.9500 |
O5—C25 | 1.447 (4) | C4—H6 | 0.9500 |
O5—C26 | 1.427 (5) | C5—H7 | 0.9500 |
C1—C2 | 1.526 (6) | C5—H8 | 0.9500 |
C1—C6 | 1.526 (6) | C6—H9 | 0.9500 |
C2—C3 | 1.532 (5) | C7—H10 | 0.9500 |
C3—C4 | 1.532 (6) | C7—H11 | 0.9500 |
C3—C7 | 1.507 (6) | C7—H12 | 0.9500 |
C4—C5 | 1.541 (6) | C8—H13 | 0.9500 |
C5—C6 | 1.536 (5) | C9—H14 | 0.9500 |
C6—C8 | 1.539 (6) | C9—H15 | 0.9500 |
C8—C9 | 1.535 (7) | C9—H16 | 0.9500 |
C8—C10 | 1.514 (7) | C10—H17 | 0.9500 |
C11—C12 | 1.543 (5) | C10—H18 | 0.9500 |
C11—C18 | 1.523 (5) | C10—H19 | 0.9500 |
C11—C24 | 1.536 (5) | C13—H20 | 0.9500 |
C12—C13 | 1.404 (6) | C14—H21 | 0.9500 |
C12—C17 | 1.380 (6) | C15—H22 | 0.9500 |
C13—C14 | 1.382 (6) | C16—H23 | 0.9500 |
C14—C15 | 1.392 (6) | C17—H24 | 0.9500 |
C15—C16 | 1.378 (6) | C19—H25 | 0.9500 |
C16—C17 | 1.395 (6) | C20—H26 | 0.9500 |
C18—C19 | 1.383 (6) | C21—H27 | 0.9500 |
C18—C23 | 1.400 (6) | C22—H28 | 0.9500 |
C19—C20 | 1.400 (6) | C23—H29 | 0.9500 |
C20—C21 | 1.370 (7) | C24—H30 | 0.9500 |
C21—C22 | 1.361 (7) | C25—H31 | 0.9500 |
C22—C23 | 1.388 (6) | C27—H32 | 0.9500 |
C24—C25 | 1.544 (6) | C27—H33 | 0.9500 |
C25—C29 | 1.524 (5) | C27—H34 | 0.9500 |
C26—C27 | 1.508 (6) | C28—H35 | 0.9500 |
C26—C28 | 1.508 (6) | C28—H36 | 0.9500 |
C29—C30 | 1.545 (5) | C28—H37 | 0.9500 |
C29—C36 | 1.518 (5) | C31—H38 | 0.9500 |
C30—C31 | 1.390 (5) | C32—H39 | 0.9500 |
C30—C35 | 1.380 (6) | C33—H40 | 0.9500 |
C31—C32 | 1.396 (6) | C34—H41 | 0.9500 |
C32—C33 | 1.351 (6) | C35—H42 | 0.9500 |
C33—C34 | 1.388 (6) | C37—H43 | 0.9500 |
C34—C35 | 1.384 (6) | C38—H44 | 0.9500 |
C36—C37 | 1.400 (5) | C39—H45 | 0.9500 |
C36—C41 | 1.400 (5) | C40—H46 | 0.9500 |
C37—C38 | 1.387 (6) | C41—H47 | 0.9500 |
O1—P1—O2 | 93.8 (1) | C3—C4—H6 | 108.9246 |
O1—P1—O3 | 95.9 (1) | C5—C4—H5 | 108.9563 |
O2—P1—O3 | 99.8 (1) | C5—C4—H6 | 108.9428 |
P1—O1—C1 | 117.6 (2) | H5—C4—H6 | 109.4236 |
P1—O2—C11 | 120.2 (2) | C4—C5—H7 | 108.7485 |
P1—O3—C29 | 126.7 (2) | C4—C5—H8 | 108.7578 |
C24—O4—C26 | 109.9 (3) | C6—C5—H7 | 108.7043 |
C25—O5—C26 | 108.7 (3) | C6—C5—H8 | 108.7014 |
O1—C1—C2 | 107.9 (3) | H7—C5—H8 | 109.4434 |
O1—C1—C6 | 106.9 (3) | C1—C6—H9 | 106.8490 |
C2—C1—C6 | 113.2 (4) | C5—C6—H9 | 106.8895 |
C1—C2—C3 | 112.6 (4) | C8—C6—H9 | 106.8677 |
C2—C3—C4 | 109.4 (4) | C3—C7—H10 | 109.4685 |
C2—C3—C7 | 111.7 (4) | C3—C7—H11 | 109.4666 |
C4—C3—C7 | 111.9 (4) | C3—C7—H12 | 109.4863 |
C3—C4—C5 | 111.6 (3) | H10—C7—H11 | 109.4433 |
C4—C5—C6 | 112.5 (4) | H10—C7—H12 | 109.4700 |
C1—C6—C5 | 109.0 (4) | H11—C7—H12 | 109.4925 |
C1—C6—C8 | 113.8 (4) | C6—C8—H13 | 106.5704 |
C5—C6—C8 | 113.0 (4) | C9—C8—H13 | 106.5347 |
C6—C8—C9 | 112.1 (4) | C10—C8—H13 | 106.6199 |
C6—C8—C10 | 114.1 (4) | C8—C9—H14 | 109.4866 |
C9—C8—C10 | 110.5 (4) | C8—C9—H15 | 109.5146 |
O2—C11—C12 | 108.5 (3) | C8—C9—H16 | 109.3866 |
O2—C11—C18 | 105.3 (3) | H14—C9—H15 | 109.5712 |
O2—C11—C24 | 106.5 (3) | H14—C9—H16 | 109.3807 |
C12—C11—C18 | 110.4 (3) | H15—C9—H16 | 109.4875 |
C12—C11—C24 | 112.9 (3) | C8—C10—H17 | 109.4334 |
C18—C11—C24 | 112.8 (3) | C8—C10—H18 | 109.5083 |
C11—C12—C13 | 118.6 (4) | C8—C10—H19 | 109.4677 |
C11—C12—C17 | 122.3 (4) | H17—C10—H18 | 109.4831 |
C13—C12—C17 | 119.0 (4) | H17—C10—H19 | 109.4112 |
C12—C13—C14 | 120.3 (4) | H18—C10—H19 | 109.5235 |
C13—C14—C15 | 120.5 (4) | C12—C13—H20 | 119.9040 |
C14—C15—C16 | 119.2 (4) | C14—C13—H20 | 119.8244 |
C15—C16—C17 | 120.7 (4) | C13—C14—H21 | 119.7610 |
C12—C17—C16 | 120.3 (4) | C15—C14—H21 | 119.7486 |
C11—C18—C19 | 120.7 (4) | C14—C15—H22 | 120.3950 |
C11—C18—C23 | 121.1 (4) | C16—C15—H22 | 120.4159 |
C19—C18—C23 | 118.2 (4) | C15—C16—H23 | 119.6595 |
C18—C19—C20 | 120.9 (4) | C17—C16—H23 | 119.6108 |
C19—C20—C21 | 119.2 (4) | C12—C17—H24 | 119.8654 |
C20—C21—C22 | 121.3 (5) | C16—C17—H24 | 119.8502 |
C21—C22—C23 | 119.8 (5) | C18—C19—H25 | 119.5520 |
C18—C23—C22 | 120.7 (4) | C20—C19—H25 | 119.5782 |
O4—C24—C11 | 111.7 (3) | C19—C20—H26 | 120.4036 |
O4—C24—C25 | 105.2 (3) | C21—C20—H26 | 120.3793 |
C11—C24—C25 | 113.9 (3) | C20—C21—H27 | 119.3628 |
O5—C25—C24 | 102.4 (3) | C22—C21—H27 | 119.3456 |
O5—C25—C29 | 108.0 (3) | C21—C22—H28 | 120.1010 |
C24—C25—C29 | 116.5 (3) | C23—C22—H28 | 120.1357 |
O4—C26—O5 | 105.1 (3) | C18—C23—H29 | 119.6340 |
O4—C26—C27 | 110.5 (3) | C22—C23—H29 | 119.6965 |
O4—C26—C28 | 108.9 (4) | O4—C24—H30 | 108.5849 |
O5—C26—C27 | 110.8 (4) | C11—C24—H30 | 108.6218 |
O5—C26—C28 | 107.3 (3) | C25—C24—H30 | 108.5869 |
C27—C26—C28 | 113.8 (4) | O5—C25—H31 | 109.8682 |
O3—C29—C25 | 106.8 (3) | C24—C25—H31 | 109.8495 |
O3—C29—C30 | 102.1 (3) | C29—C25—H31 | 109.8573 |
O3—C29—C36 | 111.2 (3) | C26—C27—H32 | 109.4821 |
C25—C29—C30 | 111.3 (3) | C26—C27—H33 | 109.5169 |
C25—C29—C36 | 115.3 (3) | C26—C27—H34 | 109.4585 |
C30—C29—C36 | 109.3 (3) | H32—C27—H33 | 109.4961 |
C29—C30—C31 | 123.9 (4) | H32—C27—H34 | 109.4120 |
C29—C30—C35 | 117.8 (4) | H33—C27—H34 | 109.4616 |
C31—C30—C35 | 118.3 (4) | C26—C28—H35 | 109.4624 |
C30—C31—C32 | 120.4 (4) | C26—C28—H36 | 109.4713 |
C31—C32—C33 | 120.7 (4) | C26—C28—H37 | 109.5012 |
C32—C33—C34 | 119.6 (4) | H35—C28—H36 | 109.4233 |
C33—C34—C35 | 120.0 (4) | H35—C28—H37 | 109.4654 |
C30—C35—C34 | 120.9 (4) | H36—C28—H37 | 109.5037 |
C29—C36—C37 | 123.2 (4) | C30—C31—H38 | 119.8525 |
C29—C36—C41 | 119.7 (4) | C32—C31—H38 | 119.7821 |
C37—C36—C41 | 117.1 (4) | C31—C32—H39 | 119.6895 |
C36—C37—C38 | 121.0 (4) | C33—C32—H39 | 119.6317 |
C37—C38—C39 | 120.7 (4) | C32—C33—H40 | 120.2003 |
C38—C39—C40 | 119.3 (4) | C34—C33—H40 | 120.1704 |
C39—C40—C41 | 120.9 (4) | C33—C34—H41 | 120.0022 |
C36—C41—C40 | 121.0 (4) | C35—C34—H41 | 119.9564 |
O1—C1—H1 | 109.5826 | C30—C35—H42 | 119.5506 |
C2—C1—H1 | 109.5495 | C34—C35—H42 | 119.5260 |
C6—C1—H1 | 109.5850 | C36—C37—H43 | 119.4778 |
C1—C2—H2 | 108.6889 | C38—C37—H43 | 119.4748 |
C1—C2—H3 | 108.6207 | C37—C38—H44 | 119.6782 |
C3—C2—H2 | 108.7278 | C39—C38—H44 | 119.6533 |
C3—C2—H3 | 108.6727 | C38—C39—H45 | 120.3142 |
H2—C2—H3 | 109.4488 | C40—C39—H45 | 120.3375 |
C2—C3—H4 | 107.9314 | C39—C40—H46 | 119.5714 |
C4—C3—H4 | 107.8991 | C41—C40—H46 | 119.5663 |
C7—C3—H4 | 107.8977 | C36—C41—H47 | 119.4996 |
C3—C4—H5 | 108.9645 | C40—C41—H47 | 119.5309 |
Experimental details
Crystal data | |
Chemical formula | C41H47O5P |
Mr | 650.79 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 133 |
a, b, c (Å) | 17.884 (1), 8.9233 (6), 22.395 (2) |
V (Å3) | 3574.0 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.12 |
Crystal size (mm) | 0.27 × 0.20 × 0.09 |
Data collection | |
Diffractometer | SMART 1K CCD diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.967, 0.989 |
No. of measured, independent and observed [I > 3.00σ(I)] reflections | 15797, 5861, 3158 |
Rint | 0.069 |
(sin θ/λ)max (Å−1) | 0.588 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.038, 0.039, 0.96 |
No. of reflections | 3158 |
No. of parameters | 424 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.21, −0.32 |
Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 2002), SAINT, SIR92 (Altomare, 1993), TEXSAN (Molecular Structure Corporation, 1985, 1992), please provide, TEXSAN.
P1—O1 | 1.610 (3) | P1—O3 | 1.656 (3) |
P1—O2 | 1.629 (3) | ||
O1—P1—O2 | 93.8 (1) | O2—P1—O3 | 99.8 (1) |
O1—P1—O3 | 95.9 (1) |
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Phosphorus-containing compounds are widely used as non-reactive ligands in metal catalysts. The title compound, (I), has been shown to induce enantioselectivity in Cu-mediated conjugate addition. This compound is also of interest as a ligand for Rh(I)-catalysed C—H bond activation. The bulky chiral phosphite is expected to induce enantioselectivity in the addition of C—H bonds across imine pi-bonds.
The title compound contains a seven-membered heterocyclic backbone comprised of TADDOL (TADDOL = α,α,α',α'-tetraphenyl-2,2'-dimethyl-1,3-dioxolane-4,5-dimethanol) and phosphorous, the third substituent on phosphorous being a menthol bonded through oxygen. Bond lengths and angles are typical for organophosphites, and the structure of the TADDOL-phosphorous ring is similar to that of previously reported compounds (Keller et al., 1998 and Sakaki et al., 1993). In these past examples, the third substituent on phosphorous has been relatively small and achiral (dimethylamine and phenyl, respectively). In the title compound, the larger chiral menthol provides an additional point of asymmetry, and is expected to increase the enantioselectivity of reactions carried out using metal complexes of this ligand.