# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2003 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Cameron Jones' 'Marcus Brym' 'Evamarie Hey-Hawkins' 'Felicite Majoumo' 'M. Waugh' _publ_contact_author_name 'Dr Cameron Jones' _publ_contact_author_address ; Department of Chemistry Cardiff University PO Box 912 Park Place Cardiff CF10 3TB UK ; _publ_contact_author_email JONESCA6@CARDIFF.AC.UK _publ_requested_journal 'New Journal of Chemistry' _publ_section_title ; Reactions of Phosphavinyl Grignard Reagents with Aldehydes: Synthesis, Characterisation and Further Reactivity of Phosphaallylic Alcohols ; data_compound_9 _database_code_CSD 212717 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H42 O8 P2 W2' _chemical_formula_weight 960.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 25.598(5) _cell_length_b 9.4670(19) _cell_length_c 17.439(4) _cell_angle_alpha 90.00 _cell_angle_beta 125.82(3) _cell_angle_gamma 90.00 _cell_volume 3426.8(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.861 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 6.846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.359 _exptl_absorpt_correction_T_max 0.613 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27823 _diffrn_reflns_av_R_equivalents 0.1137 _diffrn_reflns_av_sigmaI/netI 0.0647 _diffrn_reflns_limit_h_min -33 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 27.51 _reflns_number_total 3935 _reflns_number_gt 3013 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0429P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3935 _refine_ls_number_parameters 197 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0620 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0801 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group W1 W 0.053359(10) 0.71807(2) 0.392936(16) 0.01893(9) Uani 1 1 d . . . P1 P 0.06227(7) 0.69927(15) 0.25403(11) 0.0187(3) Uani 1 1 d . . . O1 O 0.1953(2) 0.7292(6) 0.5740(4) 0.0474(13) Uani 1 1 d . . . C1 C 0.0850(3) 0.5453(6) 0.3219(4) 0.0201(12) Uani 1 1 d . . . O2 O 0.0573(3) 1.0472(5) 0.3612(4) 0.0512(14) Uani 1 1 d . . . C2 C 0.1469(3) 0.4553(6) 0.3757(4) 0.0274(14) Uani 1 1 d . . . O3 O 0.0234(2) 0.8469(5) 0.5300(3) 0.0385(11) Uani 1 1 d . . . C3 C 0.2099(3) 0.5356(7) 0.4177(5) 0.0321(15) Uani 1 1 d . . . H3A H 0.2131 0.6121 0.4581 0.048 Uiso 1 1 calc R . . H3B H 0.2107 0.5754 0.3665 0.048 Uiso 1 1 calc R . . H3C H 0.2463 0.4708 0.4555 0.048 Uiso 1 1 calc R . . O4 O 0.0211(2) 0.4257(5) 0.4463(4) 0.0470(13) Uani 1 1 d . . . C4 C 0.1394(3) 0.3477(7) 0.3039(5) 0.0381(16) Uani 1 1 d . . . H4A H 0.1794 0.2938 0.3326 0.057 Uiso 1 1 calc R . . H4B H 0.1300 0.3975 0.2479 0.057 Uiso 1 1 calc R . . H4C H 0.1039 0.2830 0.2854 0.057 Uiso 1 1 calc R . . C5 C 0.1522(3) 0.3722(7) 0.4552(5) 0.0369(16) Uani 1 1 d . . . H5A H 0.1114 0.3232 0.4301 0.055 Uiso 1 1 calc R . . H5B H 0.1613 0.4374 0.5054 0.055 Uiso 1 1 calc R . . H5C H 0.1870 0.3029 0.4810 0.055 Uiso 1 1 calc R . . C6 C 0.1293(3) 0.7862(6) 0.2596(4) 0.0218(12) Uani 1 1 d . . . H6 H 0.1696 0.7770 0.3252 0.026 Uiso 1 1 calc R . . C7 C 0.1150(3) 0.9442(6) 0.2341(5) 0.0275(14) Uani 1 1 d . . . H7A H 0.0720 0.9546 0.1732 0.033 Uiso 1 1 calc R . . H7B H 0.1142 0.9938 0.2834 0.033 Uiso 1 1 calc R . . C8 C 0.1662(3) 1.0126(7) 0.2261(5) 0.0336(16) Uani 1 1 d . . . H8A H 0.1539 1.1119 0.2053 0.040 Uiso 1 1 calc R . . H8B H 0.2081 1.0131 0.2892 0.040 Uiso 1 1 calc R . . C9 C 0.1735(3) 0.9360(7) 0.1575(5) 0.0353(16) Uani 1 1 d . . . H9A H 0.2080 0.9814 0.1565 0.042 Uiso 1 1 calc R . . H9B H 0.1328 0.9429 0.0932 0.042 Uiso 1 1 calc R . . C10 C 0.1902(3) 0.7803(7) 0.1847(5) 0.0319(15) Uani 1 1 d . . . H10A H 0.2327 0.7730 0.2466 0.038 Uiso 1 1 calc R . . H10B H 0.1931 0.7315 0.1370 0.038 Uiso 1 1 calc R . . C11 C 0.1386(3) 0.7084(6) 0.1904(4) 0.0241(13) Uani 1 1 d . . . H11A H 0.1514 0.6094 0.2115 0.029 Uiso 1 1 calc R . . H11B H 0.0971 0.7069 0.1266 0.029 Uiso 1 1 calc R . . C12 C 0.1448(3) 0.7270(7) 0.5060(5) 0.0306(15) Uani 1 1 d . . . C13 C 0.0564(3) 0.9282(7) 0.3681(5) 0.0305(15) Uani 1 1 d . . . C14 C 0.0322(3) 0.7974(6) 0.4788(5) 0.0243(13) Uani 1 1 d . . . C15 C 0.0353(3) 0.5269(7) 0.4291(5) 0.0299(15) Uani 1 1 d . . . H1 H 0.049(3) 0.476(6) 0.289(4) 0.024(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 W1 0.02002(15) 0.01687(14) 0.02059(14) -0.00069(10) 0.01227(11) -0.00154(9) P1 0.0207(8) 0.0166(8) 0.0213(8) -0.0008(6) 0.0137(7) -0.0008(5) O1 0.029(3) 0.063(4) 0.034(3) -0.007(2) 0.009(3) -0.002(2) C1 0.023(3) 0.016(3) 0.021(3) 0.000(2) 0.013(3) -0.003(2) O2 0.085(4) 0.026(3) 0.077(4) -0.007(3) 0.067(4) -0.008(3) C2 0.028(3) 0.022(3) 0.035(4) 0.004(3) 0.020(3) 0.008(3) O3 0.059(3) 0.025(3) 0.047(3) -0.013(2) 0.040(3) -0.009(2) C3 0.026(3) 0.029(4) 0.041(4) 0.006(3) 0.019(3) 0.009(3) O4 0.065(3) 0.028(3) 0.070(4) 0.011(3) 0.052(3) 0.001(2) C4 0.046(4) 0.023(4) 0.049(4) 0.007(3) 0.029(4) 0.015(3) C5 0.031(4) 0.034(4) 0.045(4) 0.016(3) 0.022(3) 0.012(3) C6 0.017(3) 0.025(3) 0.023(3) -0.001(3) 0.011(3) -0.003(2) C7 0.035(4) 0.020(3) 0.041(4) 0.004(3) 0.029(3) -0.001(3) C8 0.041(4) 0.024(4) 0.047(4) -0.009(3) 0.032(4) -0.014(3) C9 0.046(4) 0.029(4) 0.049(4) 0.001(3) 0.038(4) -0.005(3) C10 0.028(4) 0.041(4) 0.039(4) -0.011(3) 0.027(3) -0.004(3) C11 0.026(3) 0.024(3) 0.023(3) -0.002(3) 0.015(3) -0.001(2) C12 0.034(4) 0.031(4) 0.026(4) 0.001(3) 0.017(3) 0.000(3) C13 0.049(4) 0.016(3) 0.041(4) -0.009(3) 0.034(4) -0.007(3) C14 0.032(3) 0.018(3) 0.028(3) 0.000(3) 0.021(3) -0.002(2) C15 0.038(4) 0.029(4) 0.036(4) 0.001(3) 0.029(3) 0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag W1 C12 1.993(7) . ? W1 C14 2.012(6) . ? W1 C13 2.047(6) . ? W1 C15 2.056(7) . ? W1 C1 2.457(6) . ? W1 P1 2.546(2) 2 ? W1 P1 2.5689(16) . ? P1 C1 1.749(6) . ? P1 C6 1.854(6) . ? P1 W1 2.546(2) 2 ? O1 C12 1.133(8) . ? C1 C2 1.542(8) . ? O2 C13 1.135(7) . ? C2 C3 1.526(8) . ? C2 C5 1.531(8) . ? C2 C4 1.536(9) . ? O3 C14 1.141(7) . ? O4 C15 1.127(7) . ? C6 C7 1.543(8) . ? C6 C11 1.546(8) . ? C7 C8 1.538(8) . ? C8 C9 1.501(8) . ? C9 C10 1.530(9) . ? C10 C11 1.542(8) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 W1 C14 85.4(3) . . ? C12 W1 C13 90.0(3) . . ? C14 W1 C13 81.7(2) . . ? C12 W1 C15 94.5(3) . . ? C14 W1 C15 83.9(2) . . ? C13 W1 C15 164.4(2) . . ? C12 W1 C1 89.1(2) . . ? C14 W1 C1 159.2(2) . . ? C13 W1 C1 118.4(2) . . ? C15 W1 C1 76.6(2) . . ? C12 W1 P1 177.84(19) . 2 ? C14 W1 P1 96.57(19) . 2 ? C13 W1 P1 91.18(19) . 2 ? C15 W1 P1 84.82(18) . 2 ? C1 W1 P1 88.75(14) . 2 ? C12 W1 P1 103.60(19) . . ? C14 W1 P1 159.86(17) . . ? C13 W1 P1 80.36(18) . . ? C15 W1 P1 112.85(17) . . ? C1 W1 P1 40.64(13) . . ? P1 W1 P1 74.84(6) 2 . ? C1 P1 C6 113.8(3) . . ? C1 P1 W1 118.0(2) . 2 ? C6 P1 W1 121.1(2) . 2 ? C1 P1 W1 66.25(19) . . ? C6 P1 W1 120.7(2) . . ? W1 P1 W1 104.59(6) 2 . ? C2 C1 P1 133.5(4) . . ? C2 C1 W1 125.9(4) . . ? P1 C1 W1 73.1(2) . . ? C3 C2 C5 108.2(5) . . ? C3 C2 C4 108.4(5) . . ? C5 C2 C4 107.4(5) . . ? C3 C2 C1 116.0(5) . . ? C5 C2 C1 110.4(5) . . ? C4 C2 C1 106.1(5) . . ? C7 C6 C11 110.9(5) . . ? C7 C6 P1 111.1(4) . . ? C11 C6 P1 108.0(4) . . ? C8 C7 C6 111.3(5) . . ? C9 C8 C7 112.3(5) . . ? C8 C9 C10 111.2(5) . . ? C9 C10 C11 110.5(5) . . ? C10 C11 C6 111.7(5) . . ? O1 C12 W1 175.2(6) . . ? O2 C13 W1 173.2(6) . . ? O3 C14 W1 176.0(5) . . ? O4 C15 W1 175.0(5) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.391 #(near W1) _refine_diff_density_min -2.376 #(near W1) _refine_diff_density_rms 0.253 data_compound_3a _database_code_CSD 212718 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 O P' _chemical_formula_weight 290.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.988(3) _cell_length_b 14.268(3) _cell_length_c 18.557(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.76(3) _cell_angle_gamma 90.00 _cell_volume 3407.4(12) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.132 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.732 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23049 _diffrn_reflns_av_R_equivalents 0.1052 _diffrn_reflns_av_sigmaI/netI 0.0844 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 25.06 _reflns_number_total 5894 _reflns_number_gt 4097 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0236P)^2^+1.7439P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5894 _refine_ls_number_parameters 375 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0915 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1134 _refine_ls_wR_factor_gt 0.1003 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.57447(5) 0.67468(4) 0.02091(4) 0.02614(17) Uani 1 1 d . . . P2 P 0.32664(5) 0.69631(5) 0.18914(4) 0.02903(18) Uani 1 1 d . . . O1 O 0.45239(14) 0.88052(12) 0.02241(11) 0.0312(4) Uani 1 1 d . . . O2 O 0.43317(14) 0.90512(13) 0.17577(10) 0.0318(4) Uani 1 1 d D . . C1 C 0.61269(18) 0.78691(16) 0.03228(13) 0.0233(5) Uani 1 1 d . . . C2 C 0.55183(18) 0.87250(16) -0.00128(13) 0.0248(6) Uani 1 1 d . . . H2 H 0.5926 0.9299 0.0153 0.030 Uiso 1 1 calc R . . C3 C 0.53571(18) 0.87265(15) -0.08415(13) 0.0231(5) Uani 1 1 d . . . C4 C 0.6189(2) 0.85669(17) -0.12277(14) 0.0291(6) Uani 1 1 d . . . H4 H 0.6862 0.8452 -0.0972 0.035 Uiso 1 1 calc R . . C5 C 0.6043(2) 0.85747(18) -0.19811(15) 0.0337(6) Uani 1 1 d . . . H5 H 0.6616 0.8465 -0.2238 0.040 Uiso 1 1 calc R . . C6 C 0.5074(2) 0.87405(17) -0.23617(14) 0.0331(6) Uani 1 1 d . . . H6 H 0.4976 0.8741 -0.2878 0.040 Uiso 1 1 calc R . . C7 C 0.4246(2) 0.89062(17) -0.19838(14) 0.0302(6) Uani 1 1 d . . . H7 H 0.3575 0.9020 -0.2242 0.036 Uiso 1 1 calc R . . C8 C 0.43867(19) 0.89073(16) -0.12317(14) 0.0255(6) Uani 1 1 d . . . H8 H 0.3813 0.9033 -0.0978 0.031 Uiso 1 1 calc R . . C9 C 0.71248(19) 0.80883(16) 0.08403(14) 0.0282(6) Uani 1 1 d . . . C10 C 0.7911(2) 0.8615(2) 0.04393(16) 0.0428(7) Uani 1 1 d . . . H10A H 0.8120 0.8214 0.0055 0.064 Uiso 1 1 calc R . . H10B H 0.8525 0.8777 0.0784 0.064 Uiso 1 1 calc R . . H10C H 0.7591 0.9189 0.0223 0.064 Uiso 1 1 calc R . . C11 C 0.7677(2) 0.72058(18) 0.11752(15) 0.0355(6) Uani 1 1 d . . . H11A H 0.7207 0.6861 0.1451 0.053 Uiso 1 1 calc R . . H11B H 0.8301 0.7389 0.1502 0.053 Uiso 1 1 calc R . . H11C H 0.7873 0.6806 0.0787 0.053 Uiso 1 1 calc R . . C12 C 0.6848(2) 0.86911(19) 0.14746(15) 0.0409(7) Uani 1 1 d . . . H12A H 0.6498 0.9265 0.1282 0.061 Uiso 1 1 calc R . . H12B H 0.7484 0.8855 0.1796 0.061 Uiso 1 1 calc R . . H12C H 0.6385 0.8337 0.1749 0.061 Uiso 1 1 calc R . . C13 C 0.45190(18) 0.67110(16) -0.04333(13) 0.0249(5) Uani 1 1 d . . . H13 H 0.4215 0.7355 -0.0489 0.030 Uiso 1 1 calc R . . C14 C 0.4733(2) 0.63515(18) -0.11762(14) 0.0311(6) Uani 1 1 d . . . H14A H 0.5193 0.6800 -0.1386 0.037 Uiso 1 1 calc R . . H14B H 0.5100 0.5742 -0.1113 0.037 Uiso 1 1 calc R . . C15 C 0.3735(2) 0.62299(18) -0.17004(14) 0.0351(6) Uani 1 1 d . . . H15A H 0.3902 0.5961 -0.2163 0.042 Uiso 1 1 calc R . . H15B H 0.3409 0.6850 -0.1808 0.042 Uiso 1 1 calc R . . C16 C 0.2969(2) 0.55882(19) -0.13837(15) 0.0387(7) Uani 1 1 d . . . H16A H 0.2310 0.5563 -0.1721 0.046 Uiso 1 1 calc R . . H16B H 0.3258 0.4946 -0.1335 0.046 Uiso 1 1 calc R . . C17 C 0.2751(2) 0.5933(2) -0.06442(16) 0.0388(7) Uani 1 1 d . . . H17A H 0.2294 0.5479 -0.0439 0.047 Uiso 1 1 calc R . . H17B H 0.2381 0.6541 -0.0703 0.047 Uiso 1 1 calc R . . C18 C 0.37537(19) 0.60542(17) -0.01155(14) 0.0310(6) Uani 1 1 d . . . H18A H 0.4084 0.5435 -0.0012 0.037 Uiso 1 1 calc R . . H18B H 0.3586 0.6317 0.0349 0.037 Uiso 1 1 calc R . . C19 C 0.28413(19) 0.80724(17) 0.17637(13) 0.0271(6) Uani 1 1 d . . . C20 C 0.33892(19) 0.89557(17) 0.20849(14) 0.0286(6) Uani 1 1 d . . . H20 H 0.2934 0.9501 0.1919 0.034 Uiso 1 1 calc R . . C21 C 0.35958(19) 0.89971(16) 0.29145(14) 0.0278(6) Uani 1 1 d . . . C22 C 0.2765(2) 0.89244(19) 0.33142(15) 0.0386(7) Uani 1 1 d . . . H22 H 0.2082 0.8830 0.3070 0.046 Uiso 1 1 calc R . . C23 C 0.2929(2) 0.8990(2) 0.40652(17) 0.0492(8) Uani 1 1 d . . . H23 H 0.2355 0.8944 0.4331 0.059 Uiso 1 1 calc R . . C24 C 0.3915(2) 0.9120(2) 0.44324(17) 0.0471(8) Uani 1 1 d . . . H24 H 0.4025 0.9149 0.4949 0.057 Uiso 1 1 calc R . . C25 C 0.4739(2) 0.9207(2) 0.40409(16) 0.0410(7) Uani 1 1 d . . . H25 H 0.5420 0.9305 0.4288 0.049 Uiso 1 1 calc R . . C26 C 0.4578(2) 0.91519(17) 0.32881(14) 0.0314(6) Uani 1 1 d . . . H26 H 0.5151 0.9222 0.3024 0.038 Uiso 1 1 calc R . . C27 C 0.1832(2) 0.82509(19) 0.12341(14) 0.0341(6) Uani 1 1 d . . . C28 C 0.1007(2) 0.8698(2) 0.16431(18) 0.0468(8) Uani 1 1 d . . . H28A H 0.0384 0.8836 0.1300 0.070 Uiso 1 1 calc R . . H28B H 0.1281 0.9281 0.1874 0.070 Uiso 1 1 calc R . . H28C H 0.0830 0.8263 0.2016 0.070 Uiso 1 1 calc R . . C29 C 0.2074(2) 0.8917(2) 0.06267(17) 0.0546(9) Uani 1 1 d . . . H29A H 0.2571 0.8617 0.0346 0.082 Uiso 1 1 calc R . . H29B H 0.2374 0.9499 0.0843 0.082 Uiso 1 1 calc R . . H29C H 0.1432 0.9059 0.0304 0.082 Uiso 1 1 calc R . . C30 C 0.1368(2) 0.7349(2) 0.08795(16) 0.0443(7) Uani 1 1 d . . . H30A H 0.1871 0.7056 0.0601 0.066 Uiso 1 1 calc R . . H30B H 0.0732 0.7498 0.0553 0.066 Uiso 1 1 calc R . . H30C H 0.1204 0.6916 0.1258 0.066 Uiso 1 1 calc R . . C31 C 0.44783(19) 0.69684(17) 0.25449(13) 0.0268(6) Uani 1 1 d . . . H31 H 0.4791 0.7610 0.2565 0.032 Uiso 1 1 calc R . . C32 C 0.4248(2) 0.66895(19) 0.33025(14) 0.0346(6) Uani 1 1 d . . . H32A H 0.3796 0.7170 0.3483 0.042 Uiso 1 1 calc R . . H32B H 0.3866 0.6087 0.3270 0.042 Uiso 1 1 calc R . . C33 C 0.5238(2) 0.6589(2) 0.38405(15) 0.0457(8) Uani 1 1 d . . . H33A H 0.5057 0.6359 0.4311 0.055 Uiso 1 1 calc R . . H33B H 0.5570 0.7211 0.3925 0.055 Uiso 1 1 calc R . . C34 C 0.6006(2) 0.5911(2) 0.35629(16) 0.0443(7) Uani 1 1 d . . . H34A H 0.6662 0.5908 0.3904 0.053 Uiso 1 1 calc R . . H34B H 0.5714 0.5269 0.3545 0.053 Uiso 1 1 calc R . . C35 C 0.6230(2) 0.61896(19) 0.28133(16) 0.0375(7) Uani 1 1 d . . . H35A H 0.6693 0.5717 0.2634 0.045 Uiso 1 1 calc R . . H35B H 0.6598 0.6799 0.2843 0.045 Uiso 1 1 calc R . . C36 C 0.5238(2) 0.62692(18) 0.22774(15) 0.0340(6) Uani 1 1 d . . . H36A H 0.4903 0.5646 0.2213 0.041 Uiso 1 1 calc R . . H36B H 0.5413 0.6476 0.1799 0.041 Uiso 1 1 calc R . . H1 H 0.457(2) 0.882(2) 0.0675(18) 0.049(10) Uiso 1 1 d . . . H21 H 0.451(3) 0.9609(14) 0.180(2) 0.080(13) Uiso 1 1 d D . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0294(4) 0.0211(3) 0.0265(4) -0.0004(3) -0.0018(3) -0.0002(3) P2 0.0275(4) 0.0308(4) 0.0282(4) -0.0009(3) 0.0018(3) -0.0016(3) O1 0.0320(11) 0.0387(11) 0.0233(10) -0.0026(9) 0.0050(8) 0.0081(8) O2 0.0331(11) 0.0329(11) 0.0312(10) 0.0008(9) 0.0111(8) -0.0078(8) C1 0.0244(13) 0.0246(13) 0.0210(13) -0.0008(11) 0.0038(11) 0.0009(10) C2 0.0249(14) 0.0222(13) 0.0260(14) -0.0020(11) -0.0008(11) 0.0008(10) C3 0.0290(14) 0.0140(11) 0.0262(13) -0.0012(10) 0.0038(11) -0.0024(10) C4 0.0253(14) 0.0281(14) 0.0335(15) 0.0007(12) 0.0029(12) 0.0003(10) C5 0.0334(16) 0.0363(15) 0.0341(16) -0.0016(13) 0.0135(13) 0.0001(12) C6 0.0448(17) 0.0309(14) 0.0242(14) 0.0010(12) 0.0059(13) -0.0028(12) C7 0.0315(15) 0.0298(14) 0.0277(14) 0.0023(12) -0.0024(12) 0.0000(11) C8 0.0243(14) 0.0221(12) 0.0304(14) 0.0020(11) 0.0054(11) 0.0008(10) C9 0.0287(14) 0.0248(13) 0.0296(14) -0.0027(11) -0.0018(11) -0.0015(10) C10 0.0313(16) 0.0473(17) 0.0463(18) 0.0054(14) -0.0075(13) -0.0124(13) C11 0.0293(15) 0.0378(15) 0.0359(16) -0.0002(13) -0.0081(12) 0.0033(12) C12 0.0463(18) 0.0380(16) 0.0339(16) -0.0090(13) -0.0110(13) 0.0046(13) C13 0.0267(14) 0.0195(12) 0.0271(13) 0.0010(11) -0.0010(11) -0.0012(10) C14 0.0333(15) 0.0304(14) 0.0291(14) -0.0006(12) 0.0022(12) -0.0032(11) C15 0.0415(17) 0.0337(15) 0.0280(15) -0.0022(12) -0.0035(13) -0.0017(12) C16 0.0379(17) 0.0359(15) 0.0386(17) -0.0032(13) -0.0082(13) -0.0065(12) C17 0.0307(16) 0.0392(16) 0.0458(18) 0.0034(14) 0.0027(13) -0.0070(12) C18 0.0319(15) 0.0295(14) 0.0320(15) -0.0022(12) 0.0059(12) -0.0019(11) C19 0.0229(13) 0.0354(14) 0.0237(13) 0.0024(11) 0.0059(11) -0.0023(11) C20 0.0277(14) 0.0303(14) 0.0286(14) 0.0047(11) 0.0064(12) 0.0014(11) C21 0.0280(14) 0.0245(13) 0.0319(15) -0.0010(12) 0.0076(12) -0.0007(11) C22 0.0327(16) 0.0480(17) 0.0362(16) -0.0071(14) 0.0082(13) -0.0014(13) C23 0.046(2) 0.066(2) 0.0394(18) -0.0086(16) 0.0202(16) -0.0038(16) C24 0.055(2) 0.0567(19) 0.0318(16) -0.0126(15) 0.0117(15) -0.0045(15) C25 0.0406(17) 0.0450(17) 0.0355(16) -0.0093(14) -0.0013(14) -0.0050(13) C26 0.0320(15) 0.0311(14) 0.0326(15) -0.0037(12) 0.0096(12) -0.0031(11) C27 0.0286(15) 0.0410(16) 0.0310(15) 0.0061(13) -0.0019(12) -0.0023(12) C28 0.0296(16) 0.0486(18) 0.060(2) 0.0054(16) -0.0028(14) 0.0084(13) C29 0.0444(19) 0.074(2) 0.0404(18) 0.0249(17) -0.0125(15) -0.0096(16) C30 0.0302(16) 0.0612(19) 0.0379(17) -0.0031(15) -0.0079(13) -0.0034(14) C31 0.0276(14) 0.0241(13) 0.0279(14) 0.0010(11) 0.0011(11) 0.0009(10) C32 0.0345(16) 0.0385(15) 0.0321(15) 0.0061(13) 0.0088(12) 0.0053(12) C33 0.0447(19) 0.061(2) 0.0293(16) 0.0107(15) -0.0018(14) 0.0132(15) C34 0.0378(17) 0.0467(18) 0.0455(18) 0.0098(15) -0.0043(14) 0.0095(13) C35 0.0295(15) 0.0366(15) 0.0456(17) -0.0025(14) 0.0016(13) 0.0044(12) C36 0.0332(15) 0.0359(15) 0.0330(15) -0.0031(12) 0.0050(12) 0.0027(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C1 1.681(2) . ? P1 C13 1.856(3) . ? P2 C19 1.682(3) . ? P2 C31 1.853(3) . ? O1 C2 1.424(3) . ? O2 C20 1.444(3) . ? C1 C9 1.538(3) . ? C1 C2 1.540(3) . ? C2 C3 1.524(3) . ? C3 C8 1.390(3) . ? C3 C4 1.394(3) . ? C4 C5 1.385(4) . ? C5 C6 1.378(4) . ? C6 C7 1.381(4) . ? C7 C8 1.383(3) . ? C9 C11 1.538(3) . ? C9 C10 1.539(4) . ? C9 C12 1.539(4) . ? C13 C14 1.531(3) . ? C13 C18 1.540(3) . ? C14 C15 1.522(4) . ? C15 C16 1.527(4) . ? C16 C17 1.520(4) . ? C17 C18 1.530(4) . ? C19 C20 1.528(3) . ? C19 C27 1.549(4) . ? C20 C21 1.528(4) . ? C21 C26 1.385(4) . ? C21 C22 1.393(4) . ? C22 C23 1.384(4) . ? C23 C24 1.380(4) . ? C24 C25 1.378(4) . ? C25 C26 1.387(4) . ? C27 C30 1.531(4) . ? C27 C28 1.533(4) . ? C27 C29 1.539(4) . ? C31 C32 1.529(3) . ? C31 C36 1.532(3) . ? C32 C33 1.524(4) . ? C33 C34 1.528(4) . ? C34 C35 1.513(4) . ? C35 C36 1.522(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 P1 C13 108.65(11) . . ? C19 P2 C31 108.78(12) . . ? C9 C1 C2 115.76(19) . . ? C9 C1 P1 118.80(17) . . ? C2 C1 P1 125.30(18) . . ? O1 C2 C3 107.74(19) . . ? O1 C2 C1 112.11(19) . . ? C3 C2 C1 113.73(19) . . ? C8 C3 C4 118.3(2) . . ? C8 C3 C2 121.1(2) . . ? C4 C3 C2 120.5(2) . . ? C5 C4 C3 120.5(2) . . ? C6 C5 C4 120.7(2) . . ? C5 C6 C7 119.3(2) . . ? C6 C7 C8 120.4(2) . . ? C7 C8 C3 120.8(2) . . ? C1 C9 C11 113.2(2) . . ? C1 C9 C10 110.9(2) . . ? C11 C9 C10 107.0(2) . . ? C1 C9 C12 109.1(2) . . ? C11 C9 C12 107.0(2) . . ? C10 C9 C12 109.6(2) . . ? C14 C13 C18 110.3(2) . . ? C14 C13 P1 110.06(17) . . ? C18 C13 P1 108.22(17) . . ? C15 C14 C13 111.8(2) . . ? C14 C15 C16 111.4(2) . . ? C17 C16 C15 111.3(2) . . ? C16 C17 C18 111.7(2) . . ? C17 C18 C13 111.1(2) . . ? C20 C19 C27 114.9(2) . . ? C20 C19 P2 126.46(19) . . ? C27 C19 P2 118.52(18) . . ? O2 C20 C19 106.88(19) . . ? O2 C20 C21 112.1(2) . . ? C19 C20 C21 115.7(2) . . ? C26 C21 C22 118.2(2) . . ? C26 C21 C20 122.4(2) . . ? C22 C21 C20 119.4(2) . . ? C23 C22 C21 120.4(3) . . ? C24 C23 C22 120.8(3) . . ? C25 C24 C23 119.1(3) . . ? C24 C25 C26 120.2(3) . . ? C21 C26 C25 121.1(2) . . ? C30 C27 C28 107.5(2) . . ? C30 C27 C29 108.2(2) . . ? C28 C27 C29 109.3(2) . . ? C30 C27 C19 112.6(2) . . ? C28 C27 C19 110.0(2) . . ? C29 C27 C19 109.1(2) . . ? C32 C31 C36 110.1(2) . . ? C32 C31 P2 110.26(17) . . ? C36 C31 P2 108.22(17) . . ? C33 C32 C31 112.0(2) . . ? C32 C33 C34 111.7(2) . . ? C35 C34 C33 111.1(2) . . ? C34 C35 C36 111.7(2) . . ? C35 C36 C31 111.2(2) . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.279 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.045 data_compound_5a _database_code_CSD 212719 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H52 O P2' _chemical_formula_weight 562.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.908(3) _cell_length_b 10.424(2) _cell_length_c 20.972(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.64(3) _cell_angle_gamma 90.00 _cell_volume 3230.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.923 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26407 _diffrn_reflns_av_R_equivalents 0.1011 _diffrn_reflns_av_sigmaI/netI 0.0831 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.53 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5668 _reflns_number_gt 4164 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0209P)^2^+2.5183P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0039(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5668 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0845 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.0977 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.75332(4) 0.77633(6) 0.19016(3) 0.01974(17) Uani 1 1 d . . . P2 P 0.70270(4) 0.84651(6) 0.09045(3) 0.02147(18) Uani 1 1 d . . . O1 O 0.78247(11) 0.63939(17) 0.19583(8) 0.0264(4) Uani 1 1 d . . . C1 C 0.66472(16) 0.8134(2) 0.24184(11) 0.0215(6) Uani 1 1 d . . . C2 C 0.64677(16) 0.9328(2) 0.26053(11) 0.0230(6) Uani 1 1 d . . . H2 H 0.6018 0.9351 0.2886 0.028 Uiso 1 1 calc R . . C3 C 0.68152(16) 1.0616(2) 0.24708(11) 0.0219(6) Uani 1 1 d . . . C4 C 0.71234(18) 1.1390(3) 0.29980(12) 0.0314(6) Uani 1 1 d . . . H4 H 0.7126 1.1060 0.3421 0.038 Uiso 1 1 calc R . . C5 C 0.74245(19) 1.2626(3) 0.29182(13) 0.0364(7) Uani 1 1 d . . . H5 H 0.7642 1.3129 0.3284 0.044 Uiso 1 1 calc R . . C6 C 0.74112(17) 1.3134(3) 0.23082(13) 0.0315(6) Uani 1 1 d . . . H6 H 0.7622 1.3981 0.2253 0.038 Uiso 1 1 calc R . . C7 C 0.70895(17) 1.2400(3) 0.17836(13) 0.0286(6) Uani 1 1 d . . . H7 H 0.7070 1.2748 0.1363 0.034 Uiso 1 1 calc R . . C8 C 0.67921(17) 1.1154(2) 0.18606(11) 0.0252(6) Uani 1 1 d . . . H8 H 0.6570 1.0662 0.1492 0.030 Uiso 1 1 calc R . . C9 C 0.62067(17) 0.6957(2) 0.27090(12) 0.0254(6) Uani 1 1 d . . . C10 C 0.58184(18) 0.6000(3) 0.21856(13) 0.0316(6) Uani 1 1 d . . . H10A H 0.6293 0.5750 0.1929 0.047 Uiso 1 1 calc R . . H10B H 0.5318 0.6403 0.1906 0.047 Uiso 1 1 calc R . . H10C H 0.5597 0.5237 0.2388 0.047 Uiso 1 1 calc R . . C11 C 0.54268(19) 0.7351(3) 0.30741(14) 0.0373(7) Uani 1 1 d . . . H11A H 0.4965 0.7805 0.2782 0.056 Uiso 1 1 calc R . . H11B H 0.5656 0.7916 0.3432 0.056 Uiso 1 1 calc R . . H11C H 0.5159 0.6583 0.3242 0.056 Uiso 1 1 calc R . . C12 C 0.69240(19) 0.6288(3) 0.31960(12) 0.0328(7) Uani 1 1 d . . . H12A H 0.6653 0.5541 0.3380 0.049 Uiso 1 1 calc R . . H12B H 0.7143 0.6890 0.3541 0.049 Uiso 1 1 calc R . . H12C H 0.7431 0.6010 0.2977 0.049 Uiso 1 1 calc R . . C13 C 0.84900(15) 0.8810(2) 0.21907(11) 0.0215(6) Uani 1 1 d . . . H13 H 0.8310 0.9720 0.2093 0.026 Uiso 1 1 calc R . . C14 C 0.93212(16) 0.8492(3) 0.18561(12) 0.0279(6) Uani 1 1 d . . . H14A H 0.9497 0.7586 0.1939 0.034 Uiso 1 1 calc R . . H14B H 0.9169 0.8609 0.1386 0.034 Uiso 1 1 calc R . . C15 C 1.01099(17) 0.9367(3) 0.21082(12) 0.0357(7) Uani 1 1 d . . . H15A H 1.0643 0.9142 0.1896 0.043 Uiso 1 1 calc R . . H15B H 0.9946 1.0268 0.1999 0.043 Uiso 1 1 calc R . . C16 C 1.03531(18) 0.9245(3) 0.28307(13) 0.0438(8) Uani 1 1 d . . . H16A H 1.0845 0.9854 0.2982 0.053 Uiso 1 1 calc R . . H16B H 1.0574 0.8365 0.2939 0.053 Uiso 1 1 calc R . . C17 C 0.95306(18) 0.9526(3) 0.31712(13) 0.0429(8) Uani 1 1 d . . . H17A H 0.9693 0.9391 0.3640 0.051 Uiso 1 1 calc R . . H17B H 0.9351 1.0434 0.3101 0.051 Uiso 1 1 calc R . . C18 C 0.87361(17) 0.8664(3) 0.29231(11) 0.0314(7) Uani 1 1 d . . . H18A H 0.8206 0.8893 0.3139 0.038 Uiso 1 1 calc R . . H18B H 0.8895 0.7759 0.3028 0.038 Uiso 1 1 calc R . . C19 C 0.77654(16) 0.7661(2) 0.03867(11) 0.0234(6) Uani 1 1 d . . . C20 C 0.82859(17) 0.8435(3) 0.00746(11) 0.0275(6) Uani 1 1 d . . . H20 H 0.8605 0.7972 -0.0214 0.033 Uiso 1 1 calc R . . C21 C 0.84838(17) 0.9822(3) 0.00693(12) 0.0285(6) Uani 1 1 d . . . C22 C 0.84475(18) 1.0674(3) 0.05830(12) 0.0303(6) Uani 1 1 d . . . H22 H 0.8228 1.0384 0.0963 0.036 Uiso 1 1 calc R . . C23 C 0.87290(19) 1.1930(3) 0.05406(13) 0.0352(7) Uani 1 1 d . . . H23 H 0.8708 1.2494 0.0894 0.042 Uiso 1 1 calc R . . C24 C 0.9040(2) 1.2376(3) -0.00089(14) 0.0401(7) Uani 1 1 d . . . H24 H 0.9222 1.3245 -0.0037 0.048 Uiso 1 1 calc R . . C25 C 0.9083(2) 1.1558(3) -0.05128(14) 0.0474(8) Uani 1 1 d . . . H25 H 0.9299 1.1860 -0.0892 0.057 Uiso 1 1 calc R . . C26 C 0.8816(2) 1.0297(3) -0.04748(13) 0.0407(8) Uani 1 1 d . . . H26 H 0.8859 0.9739 -0.0828 0.049 Uiso 1 1 calc R . . C27 C 0.78658(17) 0.6184(2) 0.02807(11) 0.0244(6) Uani 1 1 d . . . C28 C 0.7828(2) 0.5857(3) -0.04390(12) 0.0348(7) Uani 1 1 d . . . H28A H 0.7901 0.4929 -0.0489 0.052 Uiso 1 1 calc R . . H28B H 0.8317 0.6307 -0.0616 0.052 Uiso 1 1 calc R . . H28C H 0.7243 0.6126 -0.0669 0.052 Uiso 1 1 calc R . . C29 C 0.88022(18) 0.5816(3) 0.06293(12) 0.0321(6) Uani 1 1 d . . . H29A H 0.8839 0.6043 0.1085 0.048 Uiso 1 1 calc R . . H29B H 0.9271 0.6279 0.0437 0.048 Uiso 1 1 calc R . . H29C H 0.8894 0.4890 0.0588 0.048 Uiso 1 1 calc R . . C30 C 0.71673(18) 0.5345(3) 0.05445(12) 0.0319(7) Uani 1 1 d . . . H30A H 0.7337 0.4441 0.0513 0.048 Uiso 1 1 calc R . . H30B H 0.6572 0.5488 0.0294 0.048 Uiso 1 1 calc R . . H30C H 0.7142 0.5566 0.0996 0.048 Uiso 1 1 calc R . . C31 C 0.58611(16) 0.7771(3) 0.06887(11) 0.0256(6) Uani 1 1 d . . . H31 H 0.5846 0.6874 0.0857 0.031 Uiso 1 1 calc R . . C32 C 0.51630(16) 0.8593(3) 0.09740(12) 0.0287(6) Uani 1 1 d . . . H32A H 0.5299 0.8589 0.1449 0.034 Uiso 1 1 calc R . . H32B H 0.5204 0.9490 0.0825 0.034 Uiso 1 1 calc R . . C33 C 0.42057(17) 0.8092(3) 0.07758(13) 0.0347(7) Uani 1 1 d . . . H33A H 0.3769 0.8662 0.0953 0.042 Uiso 1 1 calc R . . H33B H 0.4150 0.7225 0.0960 0.042 Uiso 1 1 calc R . . C34 C 0.39713(18) 0.8026(3) 0.00448(12) 0.0357(7) Uani 1 1 d . . . H34A H 0.3369 0.7625 -0.0066 0.043 Uiso 1 1 calc R . . H34B H 0.3944 0.8905 -0.0136 0.043 Uiso 1 1 calc R . . C35 C 0.46758(17) 0.7250(3) -0.02472(13) 0.0349(7) Uani 1 1 d . . . H35A H 0.4537 0.7274 -0.0722 0.042 Uiso 1 1 calc R . . H35B H 0.4646 0.6345 -0.0109 0.042 Uiso 1 1 calc R . . C36 C 0.56343(17) 0.7763(3) -0.00477(11) 0.0287(6) Uani 1 1 d . . . H36A H 0.5681 0.8645 -0.0215 0.034 Uiso 1 1 calc R . . H36B H 0.6075 0.7217 -0.0236 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0216(3) 0.0189(4) 0.0184(3) -0.0002(3) 0.0017(2) -0.0001(3) P2 0.0239(4) 0.0207(4) 0.0195(3) 0.0003(3) 0.0013(2) 0.0008(3) O1 0.0306(10) 0.0232(10) 0.0253(9) 0.0005(8) 0.0032(7) 0.0031(8) C1 0.0217(13) 0.0227(14) 0.0198(12) 0.0032(10) 0.0012(10) -0.0030(11) C2 0.0216(13) 0.0268(15) 0.0209(13) 0.0015(11) 0.0045(10) -0.0004(11) C3 0.0201(13) 0.0200(14) 0.0271(14) -0.0011(11) 0.0086(10) 0.0029(11) C4 0.0420(16) 0.0277(16) 0.0246(14) -0.0015(12) 0.0048(11) -0.0019(13) C5 0.0426(17) 0.0265(17) 0.0384(17) -0.0079(13) -0.0012(13) -0.0052(13) C6 0.0269(15) 0.0209(15) 0.0470(17) 0.0006(13) 0.0063(12) -0.0019(12) C7 0.0299(15) 0.0234(15) 0.0337(15) 0.0071(12) 0.0087(11) 0.0025(12) C8 0.0286(14) 0.0228(15) 0.0243(14) -0.0038(11) 0.0039(11) 0.0022(11) C9 0.0270(14) 0.0223(15) 0.0276(14) 0.0034(11) 0.0064(11) -0.0037(11) C10 0.0324(15) 0.0242(16) 0.0382(15) 0.0063(12) 0.0042(12) -0.0104(12) C11 0.0375(16) 0.0338(17) 0.0438(17) 0.0084(14) 0.0171(13) -0.0064(14) C12 0.0436(17) 0.0274(16) 0.0275(14) 0.0058(12) 0.0053(12) -0.0045(13) C13 0.0200(13) 0.0222(14) 0.0221(13) -0.0010(10) 0.0019(10) -0.0016(11) C14 0.0256(14) 0.0343(17) 0.0242(13) -0.0030(12) 0.0044(10) -0.0005(12) C15 0.0255(15) 0.0466(19) 0.0371(16) -0.0085(14) 0.0119(12) -0.0070(14) C16 0.0243(15) 0.071(2) 0.0362(17) -0.0182(16) 0.0028(12) -0.0114(15) C17 0.0277(16) 0.071(2) 0.0304(16) -0.0181(15) 0.0058(12) -0.0123(15) C18 0.0240(14) 0.0467(19) 0.0235(13) -0.0031(12) 0.0034(11) -0.0071(13) C19 0.0263(14) 0.0253(15) 0.0177(12) 0.0012(11) 0.0003(10) 0.0019(12) C20 0.0319(15) 0.0288(16) 0.0229(13) -0.0012(12) 0.0074(11) 0.0023(13) C21 0.0299(15) 0.0278(16) 0.0288(14) 0.0031(12) 0.0078(11) -0.0009(12) C22 0.0349(15) 0.0292(16) 0.0282(15) 0.0001(12) 0.0099(12) -0.0045(13) C23 0.0416(17) 0.0280(16) 0.0382(16) -0.0058(13) 0.0133(13) -0.0064(13) C24 0.0499(19) 0.0263(17) 0.0472(18) 0.0011(14) 0.0184(14) -0.0065(14) C25 0.069(2) 0.0346(19) 0.0433(18) 0.0028(15) 0.0261(16) -0.0104(17) C26 0.058(2) 0.0349(19) 0.0328(16) -0.0032(13) 0.0207(14) -0.0071(15) C27 0.0336(15) 0.0194(14) 0.0200(13) -0.0007(10) 0.0032(11) 0.0019(11) C28 0.0514(18) 0.0251(16) 0.0274(15) -0.0065(12) 0.0038(13) 0.0035(14) C29 0.0350(16) 0.0280(16) 0.0329(15) -0.0055(12) 0.0034(12) 0.0042(13) C30 0.0389(17) 0.0225(15) 0.0339(15) -0.0023(12) 0.0037(12) -0.0029(13) C31 0.0237(13) 0.0265(15) 0.0259(13) 0.0028(11) 0.0010(10) -0.0012(12) C32 0.0250(14) 0.0321(16) 0.0280(14) -0.0004(12) 0.0003(11) 0.0004(12) C33 0.0261(15) 0.0410(18) 0.0373(16) -0.0022(13) 0.0055(12) -0.0006(13) C34 0.0277(15) 0.0403(18) 0.0365(16) -0.0018(13) -0.0053(12) -0.0041(13) C35 0.0286(15) 0.0443(19) 0.0297(15) -0.0052(13) -0.0038(11) -0.0055(14) C36 0.0268(14) 0.0320(16) 0.0264(14) -0.0015(12) 0.0001(11) 0.0010(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4923(18) . ? P1 C13 1.834(2) . ? P1 C1 1.857(2) . ? P1 P2 2.2489(10) . ? P2 C19 1.847(2) . ? P2 C31 1.882(3) . ? C1 C2 1.343(3) . ? C1 C9 1.554(3) . ? C2 C3 1.480(3) . ? C3 C8 1.393(3) . ? C3 C4 1.396(3) . ? C4 C5 1.382(4) . ? C5 C6 1.382(4) . ? C6 C7 1.373(4) . ? C7 C8 1.389(4) . ? C9 C11 1.531(4) . ? C9 C10 1.538(4) . ? C9 C12 1.543(4) . ? C13 C18 1.539(3) . ? C13 C14 1.539(3) . ? C14 C15 1.525(4) . ? C15 C16 1.516(4) . ? C16 C17 1.527(4) . ? C17 C18 1.522(4) . ? C19 C20 1.347(3) . ? C19 C27 1.566(4) . ? C20 C21 1.476(4) . ? C21 C26 1.394(4) . ? C21 C22 1.403(4) . ? C22 C23 1.382(4) . ? C23 C24 1.379(4) . ? C24 C25 1.366(4) . ? C25 C26 1.379(4) . ? C27 C30 1.519(4) . ? C27 C29 1.536(3) . ? C27 C28 1.541(3) . ? C31 C32 1.530(3) . ? C31 C36 1.536(3) . ? C32 C33 1.525(4) . ? C33 C34 1.528(4) . ? C34 C35 1.518(4) . ? C35 C36 1.531(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C13 109.72(11) . . ? O1 P1 C1 112.00(10) . . ? C13 P1 C1 105.39(11) . . ? O1 P1 P2 116.32(7) . . ? C13 P1 P2 105.31(8) . . ? C1 P1 P2 107.35(8) . . ? C19 P2 C31 106.72(11) . . ? C19 P2 P1 104.28(8) . . ? C31 P2 P1 106.47(9) . . ? C2 C1 C9 120.4(2) . . ? C2 C1 P1 123.24(18) . . ? C9 C1 P1 115.80(17) . . ? C1 C2 C3 134.2(2) . . ? C8 C3 C4 117.4(2) . . ? C8 C3 C2 125.0(2) . . ? C4 C3 C2 117.4(2) . . ? C5 C4 C3 121.4(2) . . ? C6 C5 C4 120.3(3) . . ? C7 C6 C5 119.3(3) . . ? C6 C7 C8 120.7(2) . . ? C7 C8 C3 120.9(2) . . ? C11 C9 C10 107.0(2) . . ? C11 C9 C12 107.2(2) . . ? C10 C9 C12 109.9(2) . . ? C11 C9 C1 111.9(2) . . ? C10 C9 C1 111.8(2) . . ? C12 C9 C1 108.9(2) . . ? C18 C13 C14 109.5(2) . . ? C18 C13 P1 110.06(16) . . ? C14 C13 P1 111.05(17) . . ? C15 C14 C13 110.1(2) . . ? C16 C15 C14 111.5(2) . . ? C15 C16 C17 110.6(2) . . ? C18 C17 C16 111.3(2) . . ? C17 C18 C13 110.8(2) . . ? C20 C19 C27 116.6(2) . . ? C20 C19 P2 116.2(2) . . ? C27 C19 P2 127.25(17) . . ? C19 C20 C21 135.9(2) . . ? C26 C21 C22 117.3(3) . . ? C26 C21 C20 116.6(2) . . ? C22 C21 C20 125.9(2) . . ? C23 C22 C21 120.5(2) . . ? C24 C23 C22 120.8(3) . . ? C25 C24 C23 119.5(3) . . ? C24 C25 C26 120.4(3) . . ? C25 C26 C21 121.5(3) . . ? C30 C27 C29 107.8(2) . . ? C30 C27 C28 107.0(2) . . ? C29 C27 C28 108.9(2) . . ? C30 C27 C19 115.5(2) . . ? C29 C27 C19 106.0(2) . . ? C28 C27 C19 111.4(2) . . ? C32 C31 C36 109.0(2) . . ? C32 C31 P2 110.17(18) . . ? C36 C31 P2 108.46(17) . . ? C33 C32 C31 111.2(2) . . ? C32 C33 C34 111.7(2) . . ? C35 C34 C33 110.5(2) . . ? C34 C35 C36 112.0(2) . . ? C35 C36 C31 110.4(2) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.252 _refine_diff_density_min -0.263 _refine_diff_density_rms 0.051 data_compound_5b _database_code_CSD 212720 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H52 O P2' _chemical_formula_weight 562.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.235(2) _cell_length_b 14.236(3) _cell_length_c 21.449(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.64(3) _cell_angle_gamma 90.00 _cell_volume 3333.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.902 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28003 _diffrn_reflns_av_R_equivalents 0.0829 _diffrn_reflns_av_sigmaI/netI 0.0631 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.03 _reflns_number_total 5856 _reflns_number_gt 4270 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0771P)^2^+2.3882P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5856 _refine_ls_number_parameters 359 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1067 _refine_ls_R_factor_gt 0.0751 _refine_ls_wR_factor_ref 0.1900 _refine_ls_wR_factor_gt 0.1751 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.84736(8) 0.84618(6) 0.18166(4) 0.0450(3) Uani 1 1 d . . . P2 P 0.89532(8) 0.73972(6) 0.26112(4) 0.0480(3) Uani 1 1 d . . . O1 O 0.8261(2) 0.94261(16) 0.20359(11) 0.0567(6) Uani 1 1 d . . . C1 C 0.7101(3) 0.8002(3) 0.12375(15) 0.0495(8) Uani 1 1 d . . . C2 C 0.7077(3) 0.7151(3) 0.09750(17) 0.0600(10) Uani 1 1 d . . . H2 H 0.6336 0.6989 0.0698 0.072 Uiso 1 1 calc R . . C3 C 0.8049(4) 0.6415(3) 0.10539(19) 0.0643(10) Uani 1 1 d . . . C4 C 0.8811(4) 0.6389(3) 0.0640(3) 0.0849(13) Uani 1 1 d . . . H4 H 0.8730 0.6844 0.0322 0.102 Uiso 1 1 calc R . . C5 C 0.9701(5) 0.5701(4) 0.0686(4) 0.113(2) Uani 1 1 d . . . H5 H 1.0217 0.5693 0.0404 0.136 Uiso 1 1 calc R . . C6 C 0.9801(6) 0.5039(5) 0.1151(4) 0.125(2) Uani 1 1 d U . . H6 H 1.0413 0.4587 0.1195 0.151 Uiso 1 1 calc R . . C7 C 0.9035(7) 0.5016(4) 0.1555(3) 0.118(2) Uani 1 1 d U . . H7 H 0.9111 0.4545 0.1863 0.142 Uiso 1 1 calc R . . C8 C 0.8140(5) 0.5699(3) 0.1505(2) 0.0960(16) Uani 1 1 d . . . H8 H 0.7600 0.5681 0.1774 0.115 Uiso 1 1 calc R . . C9 C 0.5987(3) 0.8678(3) 0.10404(17) 0.0583(9) Uani 1 1 d . . . C10 C 0.6365(4) 0.9543(3) 0.0712(2) 0.0731(12) Uani 1 1 d . . . H10A H 0.7051 0.9840 0.0994 0.110 Uiso 1 1 calc R . . H10B H 0.5692 0.9976 0.0609 0.110 Uiso 1 1 calc R . . H10C H 0.6589 0.9355 0.0325 0.110 Uiso 1 1 calc R . . C11 C 0.4921(4) 0.8211(4) 0.0558(2) 0.0906(15) Uani 1 1 d . . . H11A H 0.5198 0.8003 0.0191 0.136 Uiso 1 1 calc R . . H11B H 0.4268 0.8656 0.0425 0.136 Uiso 1 1 calc R . . H11C H 0.4629 0.7682 0.0757 0.136 Uiso 1 1 calc R . . C12 C 0.5519(4) 0.8991(4) 0.1624(2) 0.0819(13) Uani 1 1 d . . . H12A H 0.5259 0.8452 0.1826 0.123 Uiso 1 1 calc R . . H12B H 0.4841 0.9413 0.1488 0.123 Uiso 1 1 calc R . . H12C H 0.6165 0.9306 0.1925 0.123 Uiso 1 1 calc R . . C13 C 0.9767(3) 0.8455(3) 0.14208(16) 0.0505(8) Uani 1 1 d . . . H13 H 1.0060 0.7807 0.1416 0.061 Uiso 1 1 calc R . . C14 C 0.9400(3) 0.8809(3) 0.07231(17) 0.0614(10) Uani 1 1 d . . . H14A H 0.8741 0.8423 0.0479 0.074 Uiso 1 1 calc R . . H14B H 0.9105 0.9451 0.0716 0.074 Uiso 1 1 calc R . . C15 C 1.0486(4) 0.8770(4) 0.0418(2) 0.0802(13) Uani 1 1 d . . . H15A H 1.0739 0.8121 0.0398 0.096 Uiso 1 1 calc R . . H15B H 1.0242 0.9007 -0.0018 0.096 Uiso 1 1 calc R . . C16 C 1.1554(4) 0.9338(4) 0.0787(2) 0.0876(14) Uani 1 1 d . . . H16A H 1.1337 0.9998 0.0762 0.105 Uiso 1 1 calc R . . H16B H 1.2248 0.9256 0.0595 0.105 Uiso 1 1 calc R . . C17 C 1.1908(4) 0.9034(4) 0.1485(2) 0.0798(13) Uani 1 1 d . . . H17A H 1.2540 0.9450 0.1721 0.096 Uiso 1 1 calc R . . H17B H 1.2243 0.8404 0.1512 0.096 Uiso 1 1 calc R . . C18 C 1.0816(3) 0.9052(3) 0.17911(19) 0.0627(10) Uani 1 1 d . . . H18A H 1.1067 0.8822 0.2228 0.075 Uiso 1 1 calc R . . H18B H 1.0537 0.9695 0.1807 0.075 Uiso 1 1 calc R . . C19 C 1.0237(3) 0.8051(3) 0.31500(16) 0.0491(8) Uani 1 1 d . . . C20 C 0.9989(3) 0.8905(3) 0.33345(15) 0.0518(8) Uani 1 1 d . . . H20 H 0.9180 0.9088 0.3175 0.062 Uiso 1 1 calc R . . C21 C 1.0757(3) 0.9626(3) 0.37481(16) 0.0537(9) Uani 1 1 d . . . C22 C 1.1201(5) 1.0369(3) 0.3467(2) 0.0930(16) Uani 1 1 d . . . H22 H 1.1046 1.0402 0.3022 0.112 Uiso 1 1 calc R . . C23 C 1.1872(6) 1.1065(4) 0.3830(3) 0.120(2) Uani 1 1 d . . . H23 H 1.2175 1.1556 0.3627 0.144 Uiso 1 1 calc R . . C24 C 1.2097(5) 1.1051(4) 0.4470(3) 0.0992(17) Uani 1 1 d . . . H24 H 1.2551 1.1529 0.4711 0.119 Uiso 1 1 calc R . . C25 C 1.1660(5) 1.0335(4) 0.4766(2) 0.0942(16) Uani 1 1 d . . . H25 H 1.1813 1.0319 0.5211 0.113 Uiso 1 1 calc R . . C26 C 1.0974(4) 0.9617(3) 0.4401(2) 0.0796(13) Uani 1 1 d . . . H26 H 1.0665 0.9131 0.4606 0.096 Uiso 1 1 calc R . . C27 C 1.1444(3) 0.7498(3) 0.33552(18) 0.0590(10) Uani 1 1 d . . . C28 C 1.1339(5) 0.6846(4) 0.3904(3) 0.119(2) Uani 1 1 d U . . H28A H 1.1159 0.7209 0.4248 0.178 Uiso 1 1 calc R . . H28B H 1.2098 0.6517 0.4055 0.178 Uiso 1 1 calc R . . H28C H 1.0692 0.6401 0.3754 0.178 Uiso 1 1 calc R . . C29 C 1.2559(4) 0.8126(4) 0.3583(3) 0.1010(18) Uani 1 1 d . . . H29A H 1.2545 0.8623 0.3279 0.152 Uiso 1 1 calc R . . H29B H 1.3292 0.7761 0.3621 0.152 Uiso 1 1 calc R . . H29C H 1.2545 0.8390 0.3994 0.152 Uiso 1 1 calc R . . C30 C 1.1712(4) 0.6903(3) 0.2811(2) 0.0904(15) Uani 1 1 d . . . H30A H 1.1069 0.6451 0.2675 0.136 Uiso 1 1 calc R . . H30B H 1.2478 0.6581 0.2959 0.136 Uiso 1 1 calc R . . H30C H 1.1758 0.7302 0.2456 0.136 Uiso 1 1 calc R . . C31 C 0.7628(3) 0.7558(2) 0.29959(16) 0.0505(8) Uani 1 1 d . . . H31 H 0.7367 0.8217 0.2954 0.061 Uiso 1 1 calc R . . C32 C 0.8006(3) 0.7295(3) 0.37135(17) 0.0643(10) Uani 1 1 d . . . H32A H 0.8345 0.6665 0.3757 0.077 Uiso 1 1 calc R . . H32B H 0.8639 0.7723 0.3934 0.077 Uiso 1 1 calc R . . C33 C 0.6928(4) 0.7337(3) 0.40252(18) 0.0720(11) Uani 1 1 d . . . H33A H 0.7188 0.7121 0.4465 0.086 Uiso 1 1 calc R . . H33B H 0.6663 0.7985 0.4034 0.086 Uiso 1 1 calc R . . C34 C 0.5864(4) 0.6750(3) 0.36775(19) 0.0690(11) Uani 1 1 d . . . H34A H 0.6092 0.6091 0.3716 0.083 Uiso 1 1 calc R . . H34B H 0.5178 0.6838 0.3874 0.083 Uiso 1 1 calc R . . C35 C 0.5485(3) 0.7011(3) 0.29794(19) 0.0713(11) Uani 1 1 d . . . H35A H 0.5173 0.7649 0.2939 0.086 Uiso 1 1 calc R . . H35B H 0.4833 0.6597 0.2762 0.086 Uiso 1 1 calc R . . C36 C 0.6569(3) 0.6937(3) 0.26622(17) 0.0595(10) Uani 1 1 d . . . H36A H 0.6842 0.6290 0.2676 0.071 Uiso 1 1 calc R . . H36B H 0.6305 0.7121 0.2215 0.071 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0432(5) 0.0517(5) 0.0397(5) 0.0000(4) 0.0090(4) 0.0029(4) P2 0.0453(5) 0.0519(6) 0.0466(5) 0.0025(4) 0.0103(4) 0.0002(4) O1 0.0613(15) 0.0535(15) 0.0506(14) -0.0048(11) 0.0038(11) 0.0105(12) C1 0.0468(19) 0.060(2) 0.0408(18) 0.0004(16) 0.0080(15) 0.0004(16) C2 0.056(2) 0.073(3) 0.046(2) -0.0061(19) 0.0019(16) -0.0031(19) C3 0.074(3) 0.058(2) 0.055(2) -0.0164(19) 0.003(2) -0.003(2) C4 0.087(3) 0.069(3) 0.101(4) -0.017(3) 0.026(3) -0.004(2) C5 0.097(4) 0.092(4) 0.156(6) -0.042(4) 0.040(4) 0.001(3) C6 0.121(5) 0.094(4) 0.145(6) -0.026(4) -0.001(4) 0.033(4) C7 0.173(5) 0.071(3) 0.096(4) -0.006(3) 0.001(4) 0.020(4) C8 0.145(5) 0.069(3) 0.072(3) -0.013(3) 0.021(3) 0.017(3) C9 0.0451(19) 0.073(3) 0.052(2) 0.0008(18) 0.0024(16) 0.0082(18) C10 0.069(3) 0.077(3) 0.066(3) 0.017(2) 0.000(2) 0.020(2) C11 0.049(2) 0.114(4) 0.096(3) -0.008(3) -0.007(2) 0.001(2) C12 0.061(2) 0.110(4) 0.079(3) 0.004(3) 0.027(2) 0.027(2) C13 0.0529(19) 0.052(2) 0.0494(19) 0.0023(16) 0.0183(16) 0.0041(16) C14 0.066(2) 0.072(3) 0.051(2) 0.0001(18) 0.0220(18) 0.001(2) C15 0.092(3) 0.094(3) 0.068(3) 0.007(2) 0.046(2) 0.002(3) C16 0.071(3) 0.105(4) 0.101(4) 0.023(3) 0.050(3) 0.003(3) C17 0.055(2) 0.094(3) 0.094(3) 0.005(3) 0.027(2) -0.006(2) C18 0.053(2) 0.073(3) 0.064(2) 0.000(2) 0.0173(18) -0.0056(19) C19 0.0461(18) 0.055(2) 0.0441(18) 0.0041(16) 0.0057(15) 0.0004(16) C20 0.0479(18) 0.059(2) 0.0445(19) 0.0023(17) 0.0028(15) 0.0015(17) C21 0.051(2) 0.057(2) 0.048(2) -0.0023(17) 0.0025(16) 0.0076(17) C22 0.146(5) 0.064(3) 0.066(3) -0.005(2) 0.019(3) -0.024(3) C23 0.174(6) 0.077(4) 0.113(5) -0.024(3) 0.040(4) -0.048(4) C24 0.096(4) 0.087(4) 0.102(4) -0.038(3) -0.001(3) -0.003(3) C25 0.105(4) 0.107(4) 0.056(3) -0.022(3) -0.010(3) 0.017(3) C26 0.095(3) 0.087(3) 0.052(2) 0.003(2) 0.007(2) -0.001(3) C27 0.0461(19) 0.067(2) 0.061(2) 0.0064(19) 0.0066(17) 0.0086(17) C28 0.100(4) 0.131(4) 0.129(4) 0.065(4) 0.033(3) 0.049(3) C29 0.046(2) 0.108(4) 0.135(5) -0.027(3) -0.006(3) 0.015(2) C30 0.071(3) 0.088(3) 0.109(4) -0.015(3) 0.014(3) 0.025(2) C31 0.0460(18) 0.054(2) 0.054(2) 0.0063(16) 0.0168(15) -0.0007(16) C32 0.062(2) 0.078(3) 0.052(2) 0.0067(19) 0.0119(18) -0.009(2) C33 0.083(3) 0.091(3) 0.045(2) 0.009(2) 0.022(2) -0.003(2) C34 0.063(2) 0.081(3) 0.071(3) 0.010(2) 0.032(2) 0.001(2) C35 0.055(2) 0.098(3) 0.065(2) -0.007(2) 0.0226(19) -0.014(2) C36 0.058(2) 0.073(3) 0.050(2) -0.0048(18) 0.0180(17) -0.0106(19) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.489(2) . ? P1 C13 1.848(3) . ? P1 C1 1.856(3) . ? P1 P2 2.2493(13) . ? P2 C19 1.870(3) . ? P2 C31 1.878(3) . ? C1 C2 1.334(5) . ? C1 C9 1.556(5) . ? C2 C3 1.494(5) . ? C3 C4 1.371(6) . ? C3 C8 1.392(6) . ? C4 C5 1.387(7) . ? C5 C6 1.359(9) . ? C6 C7 1.358(9) . ? C7 C8 1.385(8) . ? C9 C10 1.529(5) . ? C9 C12 1.534(5) . ? C9 C11 1.537(5) . ? C13 C18 1.517(5) . ? C13 C14 1.540(5) . ? C14 C15 1.516(5) . ? C15 C16 1.506(7) . ? C16 C17 1.519(6) . ? C17 C18 1.522(5) . ? C19 C20 1.329(5) . ? C19 C27 1.539(5) . ? C20 C21 1.492(5) . ? C21 C26 1.364(5) . ? C21 C22 1.368(6) . ? C22 C23 1.371(7) . ? C23 C24 1.337(7) . ? C24 C25 1.352(7) . ? C25 C26 1.402(7) . ? C27 C29 1.523(6) . ? C27 C28 1.526(6) . ? C27 C30 1.530(6) . ? C31 C36 1.520(5) . ? C31 C32 1.543(5) . ? C32 C33 1.517(5) . ? C33 C34 1.505(6) . ? C34 C35 1.504(5) . ? C35 C36 1.532(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C13 110.60(15) . . ? O1 P1 C1 111.52(15) . . ? C13 P1 C1 108.07(15) . . ? O1 P1 P2 114.18(10) . . ? C13 P1 P2 105.71(12) . . ? C1 P1 P2 106.39(12) . . ? C19 P2 C31 104.09(15) . . ? C19 P2 P1 98.35(11) . . ? C31 P2 P1 100.22(11) . . ? C2 C1 C9 120.8(3) . . ? C2 C1 P1 122.3(3) . . ? C9 C1 P1 116.9(3) . . ? C1 C2 C3 130.4(3) . . ? C4 C3 C8 118.5(4) . . ? C4 C3 C2 119.8(4) . . ? C8 C3 C2 121.5(4) . . ? C3 C4 C5 121.5(5) . . ? C6 C5 C4 118.4(6) . . ? C7 C6 C5 122.1(6) . . ? C6 C7 C8 119.4(6) . . ? C7 C8 C3 120.0(5) . . ? C10 C9 C12 109.2(4) . . ? C10 C9 C11 107.1(3) . . ? C12 C9 C11 108.2(3) . . ? C10 C9 C1 109.3(3) . . ? C12 C9 C1 111.5(3) . . ? C11 C9 C1 111.4(3) . . ? C18 C13 C14 108.8(3) . . ? C18 C13 P1 110.8(2) . . ? C14 C13 P1 112.6(2) . . ? C15 C14 C13 110.4(3) . . ? C16 C15 C14 112.1(4) . . ? C15 C16 C17 110.9(4) . . ? C16 C17 C18 111.7(3) . . ? C13 C18 C17 111.7(3) . . ? C20 C19 C27 128.0(3) . . ? C20 C19 P2 117.0(3) . . ? C27 C19 P2 115.0(3) . . ? C19 C20 C21 132.4(3) . . ? C26 C21 C22 117.6(4) . . ? C26 C21 C20 122.9(4) . . ? C22 C21 C20 119.3(3) . . ? C21 C22 C23 121.2(5) . . ? C24 C23 C22 121.2(5) . . ? C23 C24 C25 119.4(5) . . ? C24 C25 C26 120.0(5) . . ? C21 C26 C25 120.5(5) . . ? C29 C27 C28 108.5(4) . . ? C29 C27 C30 106.0(4) . . ? C28 C27 C30 108.5(4) . . ? C29 C27 C19 113.2(3) . . ? C28 C27 C19 108.0(3) . . ? C30 C27 C19 112.6(3) . . ? C36 C31 C32 109.2(3) . . ? C36 C31 P2 109.6(2) . . ? C32 C31 P2 110.4(2) . . ? C33 C32 C31 111.7(3) . . ? C34 C33 C32 112.5(3) . . ? C35 C34 C33 111.2(3) . . ? C34 C35 C36 110.9(3) . . ? C31 C36 C35 111.5(3) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.761 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.045 data_compound_5c _database_code_CSD 212721 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H52 O P2' _chemical_formula_weight 562.72 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.787(2) _cell_length_b 11.073(2) _cell_length_c 15.414(3) _cell_angle_alpha 80.23(3) _cell_angle_beta 69.52(3) _cell_angle_gamma 79.05(3) _cell_volume 1682.6(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 612 _exptl_absorpt_coefficient_mu 0.154 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.636 _exptl_absorpt_correction_T_max 0.883 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14339 _diffrn_reflns_av_R_equivalents 0.0656 _diffrn_reflns_av_sigmaI/netI 0.0786 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 24.98 _reflns_number_total 5859 _reflns_number_gt 3983 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1532P)^2^+1.5963P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.000(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5859 _refine_ls_number_parameters 359 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1289 _refine_ls_R_factor_gt 0.0916 _refine_ls_wR_factor_ref 0.2767 _refine_ls_wR_factor_gt 0.2455 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.23219(11) 0.56582(10) 0.31707(8) 0.0446(4) Uani 1 1 d . . . P2 P 0.29196(11) 0.63239(10) 0.16413(8) 0.0473(4) Uani 1 1 d . . . O1 O 0.1093(3) 0.5040(3) 0.3476(2) 0.0610(9) Uani 1 1 d . . . C1 C 0.3802(4) 0.4595(4) 0.3318(3) 0.0456(10) Uani 1 1 d . . . C2 C 0.4979(4) 0.4899(4) 0.2749(3) 0.0483(11) Uani 1 1 d . . . H2 H 0.4915 0.5627 0.2355 0.058 Uiso 1 1 calc R . . C3 C 0.6379(4) 0.4290(4) 0.2626(3) 0.0441(10) Uani 1 1 d . . . C4 C 0.6889(5) 0.3224(5) 0.2188(4) 0.0652(13) Uani 1 1 d . . . H4 H 0.6349 0.2867 0.1976 0.078 Uiso 1 1 calc R . . C5 C 0.8202(6) 0.2685(6) 0.2062(4) 0.0820(18) Uani 1 1 d . . . H5 H 0.8540 0.1973 0.1761 0.098 Uiso 1 1 calc R . . C6 C 0.8983(5) 0.3180(7) 0.2371(4) 0.084(2) Uani 1 1 d . . . H6 H 0.9855 0.2801 0.2293 0.101 Uiso 1 1 calc R . . C7 C 0.8510(5) 0.4255(6) 0.2806(4) 0.0750(16) Uani 1 1 d . . . H7 H 0.9055 0.4598 0.3022 0.090 Uiso 1 1 calc R . . C8 C 0.7210(5) 0.4803(5) 0.2911(4) 0.0579(12) Uani 1 1 d . . . H8 H 0.6892 0.5538 0.3182 0.069 Uiso 1 1 calc R . . C9 C 0.3534(5) 0.3501(4) 0.4094(3) 0.0551(12) Uani 1 1 d . . . C10 C 0.4783(6) 0.2927(6) 0.4370(4) 0.095(2) Uani 1 1 d . . . H10A H 0.4533 0.2345 0.4917 0.143 Uiso 1 1 calc R . . H10B H 0.5160 0.3569 0.4496 0.143 Uiso 1 1 calc R . . H10C H 0.5431 0.2509 0.3868 0.143 Uiso 1 1 calc R . . C11 C 0.2474(5) 0.3946(5) 0.4980(4) 0.0723(15) Uani 1 1 d . . . H11A H 0.1638 0.4221 0.4869 0.108 Uiso 1 1 calc R . . H11B H 0.2748 0.4618 0.5154 0.108 Uiso 1 1 calc R . . H11C H 0.2369 0.3277 0.5475 0.108 Uiso 1 1 calc R . . C12 C 0.3015(7) 0.2507(5) 0.3780(5) 0.0858(18) Uani 1 1 d . . . H12A H 0.2775 0.1862 0.4284 0.129 Uiso 1 1 calc R . . H12B H 0.3702 0.2165 0.3257 0.129 Uiso 1 1 calc R . . H12C H 0.2245 0.2873 0.3604 0.129 Uiso 1 1 calc R . . C13 C 0.2087(4) 0.7085(4) 0.3726(3) 0.0487(11) Uani 1 1 d . . . H13 H 0.1744 0.7757 0.3331 0.058 Uiso 1 1 calc R . . C14 C 0.1022(6) 0.7055(6) 0.4659(5) 0.088(2) Uani 1 1 d . . . H14A H 0.1306 0.6395 0.5080 0.106 Uiso 1 1 calc R . . H14B H 0.0214 0.6870 0.4598 0.106 Uiso 1 1 calc R . . C15 C 0.0714(6) 0.8268(6) 0.5074(5) 0.093(2) Uani 1 1 d . . . H15A H 0.0281 0.8896 0.4712 0.111 Uiso 1 1 calc R . . H15B H 0.0093 0.8169 0.5704 0.111 Uiso 1 1 calc R . . C16 C 0.1921(6) 0.8698(5) 0.5096(4) 0.0772(16) Uani 1 1 d . . . H16A H 0.2248 0.8161 0.5559 0.093 Uiso 1 1 calc R . . H16B H 0.1682 0.9528 0.5281 0.093 Uiso 1 1 calc R . . C17 C 0.3007(6) 0.8703(5) 0.4176(5) 0.0796(17) Uani 1 1 d . . . H17A H 0.3802 0.8903 0.4245 0.096 Uiso 1 1 calc R . . H17B H 0.2736 0.9346 0.3740 0.096 Uiso 1 1 calc R . . C18 C 0.3350(5) 0.7468(5) 0.3772(4) 0.0682(14) Uani 1 1 d . . . H18A H 0.3738 0.6839 0.4161 0.082 Uiso 1 1 calc R . . H18B H 0.4003 0.7544 0.3152 0.082 Uiso 1 1 calc R . . C19 C 0.1510(4) 0.7620(4) 0.1663(3) 0.0481(10) Uani 1 1 d . . . C20 C 0.0271(4) 0.7375(4) 0.2135(3) 0.0518(11) Uani 1 1 d . . . H20 H 0.0232 0.6558 0.2402 0.062 Uiso 1 1 calc R . . C21 C -0.1064(4) 0.8154(4) 0.2318(3) 0.0474(10) Uani 1 1 d . . . C22 C -0.1896(5) 0.8006(5) 0.1843(4) 0.0705(15) Uani 1 1 d . . . H22 H -0.1604 0.7445 0.1403 0.085 Uiso 1 1 calc R . . C23 C -0.3154(5) 0.8687(6) 0.2019(5) 0.0842(18) Uani 1 1 d . . . H23 H -0.3695 0.8596 0.1686 0.101 Uiso 1 1 calc R . . C24 C -0.3604(5) 0.9484(6) 0.2673(5) 0.0800(18) Uani 1 1 d . . . H24 H -0.4448 0.9949 0.2785 0.096 Uiso 1 1 calc R . . C25 C -0.2822(6) 0.9601(6) 0.3163(5) 0.0862(18) Uani 1 1 d . . . H25 H -0.3138 1.0141 0.3619 0.103 Uiso 1 1 calc R . . C26 C -0.1564(5) 0.8935(5) 0.3001(4) 0.0709(15) Uani 1 1 d . . . H26 H -0.1050 0.9014 0.3356 0.085 Uiso 1 1 calc R . . C27 C 0.1948(5) 0.8826(4) 0.1087(4) 0.0611(13) Uani 1 1 d . . . C28 C 0.0862(7) 0.9876(6) 0.1093(6) 0.113(2) Uani 1 1 d U . . H28A H 0.0207 0.9629 0.0894 0.169 Uiso 1 1 calc R . . H28B H 0.1228 1.0565 0.0677 0.169 Uiso 1 1 calc R . . H28C H 0.0448 1.0112 0.1713 0.169 Uiso 1 1 calc R . . C29 C 0.2661(8) 0.8540(7) 0.0062(5) 0.111(2) Uani 1 1 d U . . H29A H 0.2036 0.8299 -0.0168 0.166 Uiso 1 1 calc R . . H29B H 0.3388 0.7880 0.0037 0.166 Uiso 1 1 calc R . . H29C H 0.3000 0.9266 -0.0314 0.166 Uiso 1 1 calc R . . C30 C 0.2995(7) 0.9239(7) 0.1361(6) 0.109(2) Uani 1 1 d U . . H30A H 0.3333 0.9933 0.0935 0.164 Uiso 1 1 calc R . . H30B H 0.3713 0.8571 0.1342 0.164 Uiso 1 1 calc R . . H30C H 0.2607 0.9477 0.1981 0.164 Uiso 1 1 calc R . . C31 C 0.2433(5) 0.5011(4) 0.1271(3) 0.0503(11) Uani 1 1 d . . . H31 H 0.1608 0.4777 0.1745 0.060 Uiso 1 1 calc R . . C32 C 0.3535(5) 0.3900(5) 0.1201(4) 0.0614(13) Uani 1 1 d . . . H32A H 0.4370 0.4137 0.0762 0.074 Uiso 1 1 calc R . . H32B H 0.3654 0.3651 0.1804 0.074 Uiso 1 1 calc R . . C33 C 0.3194(6) 0.2812(5) 0.0883(4) 0.0730(16) Uani 1 1 d . . . H33A H 0.3936 0.2144 0.0808 0.088 Uiso 1 1 calc R . . H33B H 0.2419 0.2514 0.1360 0.088 Uiso 1 1 calc R . . C34 C 0.2907(6) 0.3152(5) -0.0015(4) 0.0748(16) Uani 1 1 d . . . H34A H 0.2616 0.2455 -0.0158 0.090 Uiso 1 1 calc R . . H34B H 0.3722 0.3329 -0.0513 0.090 Uiso 1 1 calc R . . C35 C 0.1839(6) 0.4271(6) 0.0025(4) 0.0759(16) Uani 1 1 d . . . H35A H 0.1736 0.4503 -0.0585 0.091 Uiso 1 1 calc R . . H35B H 0.0992 0.4059 0.0461 0.091 Uiso 1 1 calc R . . C36 C 0.2192(6) 0.5352(5) 0.0322(4) 0.0654(13) Uani 1 1 d . . . H36A H 0.1472 0.6038 0.0369 0.079 Uiso 1 1 calc R . . H36B H 0.2992 0.5617 -0.0147 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0408(6) 0.0394(6) 0.0570(7) -0.0043(5) -0.0232(5) -0.0009(5) P2 0.0472(7) 0.0394(6) 0.0576(8) -0.0045(5) -0.0232(5) -0.0007(5) O1 0.0538(19) 0.0598(19) 0.075(2) 0.0020(17) -0.0300(17) -0.0119(15) C1 0.042(2) 0.039(2) 0.056(3) -0.0013(19) -0.022(2) 0.0015(18) C2 0.044(2) 0.042(2) 0.060(3) 0.001(2) -0.026(2) 0.0006(19) C3 0.035(2) 0.046(2) 0.046(2) -0.0002(19) -0.0151(18) 0.0064(18) C4 0.060(3) 0.063(3) 0.072(3) -0.016(3) -0.024(3) 0.005(2) C5 0.070(4) 0.079(4) 0.073(4) -0.013(3) -0.011(3) 0.030(3) C6 0.036(3) 0.109(5) 0.080(4) 0.016(4) -0.007(3) 0.010(3) C7 0.047(3) 0.102(4) 0.078(4) 0.014(3) -0.029(3) -0.020(3) C8 0.049(3) 0.058(3) 0.067(3) -0.003(2) -0.021(2) -0.007(2) C9 0.051(3) 0.048(2) 0.061(3) 0.009(2) -0.024(2) -0.001(2) C10 0.064(3) 0.107(5) 0.090(4) 0.041(4) -0.029(3) 0.009(3) C11 0.069(3) 0.075(3) 0.064(3) 0.009(3) -0.021(3) -0.005(3) C12 0.114(5) 0.046(3) 0.091(4) -0.001(3) -0.024(4) -0.022(3) C13 0.050(2) 0.041(2) 0.062(3) -0.011(2) -0.031(2) 0.0073(19) C14 0.058(3) 0.086(4) 0.113(5) -0.051(4) 0.005(3) -0.020(3) C15 0.067(4) 0.103(5) 0.105(5) -0.060(4) -0.005(3) -0.008(3) C16 0.090(4) 0.069(3) 0.087(4) -0.039(3) -0.045(3) 0.013(3) C17 0.074(4) 0.063(3) 0.111(5) -0.030(3) -0.031(3) -0.013(3) C18 0.061(3) 0.064(3) 0.084(4) -0.023(3) -0.021(3) -0.012(3) C19 0.052(3) 0.039(2) 0.055(3) 0.0035(19) -0.027(2) 0.0004(19) C20 0.052(3) 0.038(2) 0.068(3) 0.002(2) -0.032(2) 0.0034(19) C21 0.047(2) 0.040(2) 0.058(3) -0.004(2) -0.027(2) 0.0036(18) C22 0.063(3) 0.077(3) 0.084(4) -0.033(3) -0.040(3) 0.012(3) C23 0.054(3) 0.098(4) 0.111(5) -0.021(4) -0.047(3) 0.009(3) C24 0.050(3) 0.070(4) 0.102(5) -0.005(3) -0.017(3) 0.016(3) C25 0.083(4) 0.077(4) 0.085(4) -0.030(3) -0.014(3) 0.013(3) C26 0.066(3) 0.068(3) 0.085(4) -0.022(3) -0.033(3) 0.005(3) C27 0.067(3) 0.041(2) 0.070(3) 0.008(2) -0.028(3) 0.001(2) C28 0.103(4) 0.081(3) 0.127(4) 0.024(3) -0.027(3) 0.003(3) C29 0.124(4) 0.096(4) 0.093(4) 0.004(3) -0.016(3) -0.022(3) C30 0.112(4) 0.089(4) 0.132(4) 0.003(3) -0.041(3) -0.042(3) C31 0.051(2) 0.044(2) 0.052(3) -0.011(2) -0.008(2) -0.009(2) C32 0.060(3) 0.061(3) 0.071(3) -0.018(2) -0.031(3) 0.000(2) C33 0.072(3) 0.047(3) 0.106(5) -0.028(3) -0.033(3) 0.002(2) C34 0.080(4) 0.077(4) 0.073(4) -0.033(3) -0.018(3) -0.018(3) C35 0.088(4) 0.090(4) 0.060(3) -0.020(3) -0.031(3) -0.013(3) C36 0.071(3) 0.064(3) 0.066(3) -0.006(3) -0.032(3) -0.004(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.499(3) . ? P1 C1 1.853(4) . ? P1 C13 1.857(4) . ? P1 P2 2.2459(18) . ? P2 C31 1.869(4) . ? P2 C19 1.878(4) . ? C1 C2 1.332(6) . ? C1 C9 1.543(6) . ? C2 C3 1.492(6) . ? C3 C8 1.368(6) . ? C3 C4 1.384(7) . ? C4 C5 1.388(7) . ? C5 C6 1.335(9) . ? C6 C7 1.388(9) . ? C7 C8 1.383(7) . ? C9 C11 1.530(7) . ? C9 C12 1.537(7) . ? C9 C10 1.544(7) . ? C13 C14 1.493(7) . ? C13 C18 1.530(6) . ? C14 C15 1.516(7) . ? C15 C16 1.481(8) . ? C16 C17 1.490(8) . ? C17 C18 1.525(7) . ? C19 C20 1.334(6) . ? C19 C27 1.529(6) . ? C20 C21 1.491(6) . ? C21 C26 1.371(7) . ? C21 C22 1.387(7) . ? C22 C23 1.380(7) . ? C23 C24 1.353(9) . ? C24 C25 1.349(9) . ? C25 C26 1.375(8) . ? C27 C28 1.484(8) . ? C27 C30 1.503(8) . ? C27 C29 1.553(9) . ? C31 C32 1.528(6) . ? C31 C36 1.547(7) . ? C32 C33 1.525(7) . ? C33 C34 1.494(8) . ? C34 C35 1.517(8) . ? C35 C36 1.507(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C1 112.84(19) . . ? O1 P1 C13 113.7(2) . . ? C1 P1 C13 110.16(19) . . ? O1 P1 P2 111.00(15) . . ? C1 P1 P2 104.75(15) . . ? C13 P1 P2 103.63(15) . . ? C31 P2 C19 104.5(2) . . ? C31 P2 P1 96.80(15) . . ? C19 P2 P1 98.92(15) . . ? C2 C1 C9 128.0(4) . . ? C2 C1 P1 115.1(3) . . ? C9 C1 P1 116.9(3) . . ? C1 C2 C3 132.1(4) . . ? C8 C3 C4 118.2(4) . . ? C8 C3 C2 120.6(4) . . ? C4 C3 C2 121.1(4) . . ? C3 C4 C5 120.3(5) . . ? C6 C5 C4 120.4(6) . . ? C5 C6 C7 120.9(5) . . ? C8 C7 C6 118.4(5) . . ? C3 C8 C7 121.7(5) . . ? C11 C9 C12 108.5(4) . . ? C11 C9 C1 110.0(4) . . ? C12 C9 C1 109.7(4) . . ? C11 C9 C10 105.9(4) . . ? C12 C9 C10 110.0(5) . . ? C1 C9 C10 112.7(4) . . ? C14 C13 C18 111.0(4) . . ? C14 C13 P1 111.9(3) . . ? C18 C13 P1 116.3(3) . . ? C13 C14 C15 112.5(5) . . ? C16 C15 C14 113.0(5) . . ? C15 C16 C17 112.4(5) . . ? C16 C17 C18 113.1(5) . . ? C17 C18 C13 109.9(4) . . ? C20 C19 C27 128.2(4) . . ? C20 C19 P2 117.4(3) . . ? C27 C19 P2 114.3(3) . . ? C19 C20 C21 132.5(4) . . ? C26 C21 C22 117.8(4) . . ? C26 C21 C20 122.8(4) . . ? C22 C21 C20 119.1(4) . . ? C23 C22 C21 120.5(5) . . ? C24 C23 C22 120.4(5) . . ? C25 C24 C23 119.5(5) . . ? C24 C25 C26 121.1(6) . . ? C21 C26 C25 120.5(5) . . ? C28 C27 C30 109.0(5) . . ? C28 C27 C19 115.8(5) . . ? C30 C27 C19 111.5(4) . . ? C28 C27 C29 107.8(5) . . ? C30 C27 C29 104.9(5) . . ? C19 C27 C29 107.1(4) . . ? C32 C31 C36 109.0(4) . . ? C32 C31 P2 109.4(3) . . ? C36 C31 P2 112.4(3) . . ? C33 C32 C31 111.3(4) . . ? C34 C33 C32 112.3(5) . . ? C33 C34 C35 112.0(4) . . ? C36 C35 C34 111.3(5) . . ? C35 C36 C31 111.5(4) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 1.525 #(near P2) _refine_diff_density_min -0.378 _refine_diff_density_rms 0.070 data_compound_6 _database_code_CSD 212722 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 O P' _chemical_formula_weight 290.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.3490(13) _cell_length_b 14.028(3) _cell_length_c 19.120(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.05(3) _cell_angle_gamma 90.00 _cell_volume 1696.3(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.771 _exptl_absorpt_correction_T_max 0.960 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29071 _diffrn_reflns_av_R_equivalents 0.0975 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 3.09 _diffrn_reflns_theta_max 25.94 _reflns_number_total 3294 _reflns_number_gt 2636 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0441P)^2^+0.6276P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0119(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3294 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1024 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.51968(7) 0.73991(3) 0.28184(2) 0.02474(15) Uani 1 1 d . . . O1 O 0.32274(18) 0.79719(9) 0.28194(6) 0.0350(3) Uani 1 1 d . . . C1 C 0.7565(3) 0.79786(11) 0.32215(8) 0.0225(4) Uani 1 1 d . . . C2 C 0.8601(3) 0.86212(12) 0.28637(8) 0.0249(4) Uani 1 1 d . . . H2 H 0.9799 0.8887 0.3103 0.030 Uiso 1 1 calc R . . C3 C 0.8085(3) 0.89633(11) 0.21361(8) 0.0242(4) Uani 1 1 d . . . C4 C 0.6105(3) 0.93226(12) 0.18968(9) 0.0302(4) Uani 1 1 d . . . H4 H 0.5053 0.9373 0.2204 0.036 Uiso 1 1 calc R . . C5 C 0.5693(3) 0.96061(12) 0.12017(10) 0.0356(5) Uani 1 1 d . . . H5 H 0.4367 0.9845 0.1046 0.043 Uiso 1 1 calc R . . C6 C 0.7237(3) 0.95354(13) 0.07422(10) 0.0379(5) Uani 1 1 d . . . H6 H 0.6947 0.9716 0.0276 0.046 Uiso 1 1 calc R . . C7 C 0.9219(3) 0.91956(14) 0.09757(10) 0.0375(5) Uani 1 1 d . . . H7 H 1.0265 0.9151 0.0666 0.045 Uiso 1 1 calc R . . C8 C 0.9652(3) 0.89218(12) 0.16705(9) 0.0298(4) Uani 1 1 d . . . H8 H 1.0999 0.8709 0.1827 0.036 Uiso 1 1 calc R . . C9 C 0.8352(3) 0.76595(12) 0.39705(9) 0.0264(4) Uani 1 1 d . . . C10 C 0.9341(3) 0.66633(13) 0.39369(9) 0.0337(4) Uani 1 1 d . . . H10A H 0.9863 0.6466 0.4401 0.051 Uiso 1 1 calc R . . H10B H 1.0488 0.6682 0.3642 0.051 Uiso 1 1 calc R . . H10C H 0.8291 0.6219 0.3747 0.051 Uiso 1 1 calc R . . C11 C 0.6513(3) 0.76441(14) 0.44409(9) 0.0347(4) Uani 1 1 d . . . H11A H 0.5456 0.7202 0.4253 0.052 Uiso 1 1 calc R . . H11B H 0.5906 0.8270 0.4457 0.052 Uiso 1 1 calc R . . H11C H 0.7027 0.7451 0.4907 0.052 Uiso 1 1 calc R . . C12 C 1.0054(3) 0.83319(13) 0.43088(9) 0.0353(4) Uani 1 1 d . . . H12A H 1.0474 0.8122 0.4778 0.053 Uiso 1 1 calc R . . H12B H 0.9496 0.8967 0.4321 0.053 Uiso 1 1 calc R . . H12C H 1.1258 0.8327 0.4038 0.053 Uiso 1 1 calc R . . C13 C 0.5719(2) 0.69074(12) 0.19726(8) 0.0237(4) Uani 1 1 d . . . H13 H 0.5937 0.7438 0.1654 0.028 Uiso 1 1 calc R . . C14 C 0.7710(3) 0.62843(12) 0.20236(9) 0.0272(4) Uani 1 1 d . . . H14A H 0.8928 0.6667 0.2187 0.033 Uiso 1 1 calc R . . H14B H 0.7565 0.5777 0.2361 0.033 Uiso 1 1 calc R . . C15 C 0.8051(3) 0.58538(13) 0.13091(9) 0.0300(4) Uani 1 1 d . . . H15A H 0.8329 0.6361 0.0984 0.036 Uiso 1 1 calc R . . H15B H 0.9278 0.5439 0.1356 0.036 Uiso 1 1 calc R . . C16 C 0.6133(3) 0.52868(13) 0.10145(10) 0.0335(4) Uani 1 1 d . . . H16A H 0.5939 0.4742 0.1315 0.040 Uiso 1 1 calc R . . H16B H 0.6374 0.5050 0.0552 0.040 Uiso 1 1 calc R . . C17 C 0.4141(3) 0.58983(13) 0.09644(9) 0.0322(4) Uani 1 1 d . . . H17A H 0.2934 0.5508 0.0803 0.039 Uiso 1 1 calc R . . H17B H 0.4273 0.6400 0.0622 0.039 Uiso 1 1 calc R . . C18 C 0.3763(3) 0.63439(13) 0.16723(9) 0.0280(4) Uani 1 1 d . . . H18A H 0.3450 0.5846 0.1999 0.034 Uiso 1 1 calc R . . H18B H 0.2552 0.6767 0.1614 0.034 Uiso 1 1 calc R . . H1 H 0.510(3) 0.6587(12) 0.3202(9) 0.026(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0212(2) 0.0313(3) 0.0217(2) -0.00167(17) 0.00189(17) 0.00043(17) O1 0.0229(7) 0.0503(8) 0.0318(7) -0.0061(6) 0.0023(5) 0.0072(5) C1 0.0230(9) 0.0242(9) 0.0204(8) -0.0020(6) 0.0017(7) 0.0043(6) C2 0.0250(9) 0.0264(9) 0.0230(9) -0.0037(7) -0.0004(7) 0.0017(7) C3 0.0303(9) 0.0195(8) 0.0223(8) -0.0008(6) -0.0004(7) -0.0032(6) C4 0.0339(10) 0.0273(9) 0.0292(10) -0.0019(7) 0.0022(8) 0.0043(7) C5 0.0418(11) 0.0293(10) 0.0336(10) 0.0020(8) -0.0084(9) 0.0054(8) C6 0.0509(13) 0.0384(11) 0.0230(9) 0.0051(8) -0.0053(9) -0.0045(9) C7 0.0416(12) 0.0454(11) 0.0258(10) 0.0009(8) 0.0046(8) -0.0086(9) C8 0.0301(10) 0.0312(10) 0.0275(9) -0.0003(7) -0.0010(8) -0.0030(7) C9 0.0277(9) 0.0308(9) 0.0200(8) 0.0007(7) -0.0008(7) 0.0027(7) C10 0.0381(11) 0.0343(10) 0.0281(10) 0.0042(8) -0.0010(8) 0.0065(8) C11 0.0385(11) 0.0441(11) 0.0218(9) 0.0008(8) 0.0045(8) 0.0037(8) C12 0.0391(11) 0.0404(11) 0.0248(10) 0.0015(8) -0.0072(8) -0.0026(8) C13 0.0217(9) 0.0264(9) 0.0230(8) -0.0014(7) 0.0023(7) -0.0011(7) C14 0.0236(9) 0.0297(9) 0.0280(9) -0.0038(7) 0.0011(7) -0.0002(7) C15 0.0278(10) 0.0327(10) 0.0297(10) -0.0047(7) 0.0031(7) 0.0027(7) C16 0.0344(10) 0.0356(10) 0.0307(10) -0.0091(8) 0.0032(8) -0.0014(8) C17 0.0294(10) 0.0400(11) 0.0265(9) -0.0056(8) -0.0017(8) -0.0050(8) C18 0.0224(9) 0.0341(9) 0.0270(9) -0.0014(7) 0.0003(7) -0.0025(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4865(13) . ? P1 C13 1.8153(17) . ? P1 C1 1.8197(17) . ? C1 C2 1.339(2) . ? C1 C9 1.541(2) . ? C2 C3 1.481(2) . ? C3 C4 1.394(2) . ? C3 C8 1.394(3) . ? C4 C5 1.390(2) . ? C5 C6 1.376(3) . ? C6 C7 1.383(3) . ? C7 C8 1.387(2) . ? C9 C12 1.534(2) . ? C9 C10 1.536(2) . ? C9 C11 1.536(3) . ? C13 C14 1.533(2) . ? C13 C18 1.540(2) . ? C14 C15 1.526(2) . ? C15 C16 1.521(2) . ? C16 C17 1.524(2) . ? C17 C18 1.529(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C13 115.22(8) . . ? O1 P1 C1 114.94(8) . . ? C13 P1 C1 109.77(8) . . ? C2 C1 C9 122.44(15) . . ? C2 C1 P1 120.61(12) . . ? C9 C1 P1 116.89(12) . . ? C1 C2 C3 128.32(15) . . ? C4 C3 C8 118.66(15) . . ? C4 C3 C2 122.98(16) . . ? C8 C3 C2 118.36(15) . . ? C5 C4 C3 120.39(17) . . ? C6 C5 C4 120.34(18) . . ? C5 C6 C7 119.87(17) . . ? C6 C7 C8 120.18(18) . . ? C7 C8 C3 120.52(17) . . ? C12 C9 C10 107.57(14) . . ? C12 C9 C11 107.79(15) . . ? C10 C9 C11 110.27(15) . . ? C12 C9 C1 111.85(14) . . ? C10 C9 C1 109.01(13) . . ? C11 C9 C1 110.31(14) . . ? C14 C13 C18 111.37(14) . . ? C14 C13 P1 111.97(11) . . ? C18 C13 P1 108.83(11) . . ? C15 C14 C13 110.49(14) . . ? C16 C15 C14 111.48(15) . . ? C15 C16 C17 111.22(15) . . ? C16 C17 C18 111.64(14) . . ? C17 C18 C13 110.82(14) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.94 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.284 _refine_diff_density_min -0.310 _refine_diff_density_rms 0.045 data_compound_2 _database_code_CSD 212723 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H29 O2 P' _chemical_formula_weight 308.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.0830(12) _cell_length_b 19.234(4) _cell_length_c 14.925(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.12(3) _cell_angle_gamma 90.00 _cell_volume 1719.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.880 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_process_details 'Sortav (Blessing, 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16590 _diffrn_reflns_av_R_equivalents 0.1020 _diffrn_reflns_av_sigmaI/netI 0.0701 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.97 _diffrn_reflns_theta_max 24.92 _reflns_number_total 2988 _reflns_number_gt 2257 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0285P)^2^+1.6792P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2988 _refine_ls_number_parameters 201 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0556 _refine_ls_wR_factor_ref 0.1195 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.25614(11) 0.71502(4) 0.83116(5) 0.0233(2) Uani 1 1 d . . . O1 O 0.4453(3) 0.70372(10) 0.78054(13) 0.0321(5) Uani 1 1 d . . . O2 O 0.1564(4) 0.64649(11) 0.63561(14) 0.0385(5) Uani 1 1 d . . . C1 C 0.0007(4) 0.67145(14) 0.77525(17) 0.0223(6) Uani 1 1 d . . . H1 H -0.1261 0.6980 0.7932 0.027 Uiso 1 1 calc R . . C2 C -0.0214(5) 0.68074(15) 0.67031(19) 0.0301(7) Uani 1 1 d . . . H2 H -0.1634 0.6573 0.6419 0.036 Uiso 1 1 calc R . . C3 C -0.0444(4) 0.75702(14) 0.64319(17) 0.0249(6) Uani 1 1 d . . . C4 C -0.2318(4) 0.79442(15) 0.65864(18) 0.0277(6) Uani 1 1 d . . . H4 H -0.3469 0.7713 0.6825 0.033 Uiso 1 1 calc R . . C5 C -0.2507(5) 0.86424(16) 0.6397(2) 0.0337(7) Uani 1 1 d . . . H5 H -0.3782 0.8890 0.6509 0.040 Uiso 1 1 calc R . . C6 C -0.0857(5) 0.89881(16) 0.6044(2) 0.0351(7) Uani 1 1 d . . . H6 H -0.0978 0.9473 0.5926 0.042 Uiso 1 1 calc R . . C7 C 0.0960(5) 0.86239(16) 0.58636(19) 0.0333(7) Uani 1 1 d . . . H7 H 0.2082 0.8857 0.5609 0.040 Uiso 1 1 calc R . . C8 C 0.1171(5) 0.79159(15) 0.60515(17) 0.0297(7) Uani 1 1 d . . . H8 H 0.2425 0.7668 0.5919 0.036 Uiso 1 1 calc R . . C9 C -0.0227(4) 0.59484(14) 0.80860(18) 0.0261(6) Uani 1 1 d . . . C10 C -0.2043(5) 0.55589(15) 0.7430(2) 0.0337(7) Uani 1 1 d . . . H10A H -0.2361 0.5115 0.7702 0.051 Uiso 1 1 calc R . . H10B H -0.1521 0.5473 0.6855 0.051 Uiso 1 1 calc R . . H10C H -0.3405 0.5841 0.7314 0.051 Uiso 1 1 calc R . . C11 C -0.0986(5) 0.59847(16) 0.90149(19) 0.0328(7) Uani 1 1 d . . . H11A H -0.2443 0.6215 0.8945 0.049 Uiso 1 1 calc R . . H11B H 0.0110 0.6249 0.9442 0.049 Uiso 1 1 calc R . . H11C H -0.1108 0.5513 0.9249 0.049 Uiso 1 1 calc R . . C12 C 0.1948(5) 0.55321(15) 0.8181(2) 0.0348(7) Uani 1 1 d . . . H12A H 0.1680 0.5054 0.8360 0.052 Uiso 1 1 calc R . . H12B H 0.3081 0.5747 0.8647 0.052 Uiso 1 1 calc R . . H12C H 0.2477 0.5529 0.7598 0.052 Uiso 1 1 calc R . . C13 C 0.1969(4) 0.80557(14) 0.85123(18) 0.0243(6) Uani 1 1 d . . . H13 H 0.1174 0.8256 0.7926 0.029 Uiso 1 1 calc R . . C14 C 0.4135(5) 0.84645(15) 0.8798(2) 0.0308(7) Uani 1 1 d . . . H14A H 0.4956 0.8280 0.9381 0.037 Uiso 1 1 calc R . . H14B H 0.5097 0.8411 0.8332 0.037 Uiso 1 1 calc R . . C15 C 0.3600(5) 0.92312(15) 0.8905(2) 0.0349(7) Uani 1 1 d . . . H15A H 0.5004 0.9491 0.9107 0.042 Uiso 1 1 calc R . . H15B H 0.2879 0.9421 0.8309 0.042 Uiso 1 1 calc R . . C16 C 0.2060(5) 0.93339(16) 0.9593(2) 0.0351(7) Uani 1 1 d . . . H16A H 0.1660 0.9832 0.9614 0.042 Uiso 1 1 calc R . . H16B H 0.2854 0.9199 1.0205 0.042 Uiso 1 1 calc R . . C17 C -0.0068(5) 0.89015(16) 0.9351(2) 0.0394(8) Uani 1 1 d . . . H17A H -0.0960 0.8946 0.9843 0.047 Uiso 1 1 calc R . . H17B H -0.0975 0.9085 0.8785 0.047 Uiso 1 1 calc R . . C18 C 0.0443(5) 0.81360(15) 0.9220(2) 0.0328(7) Uani 1 1 d . . . H18A H -0.0968 0.7880 0.9015 0.039 Uiso 1 1 calc R . . H18B H 0.1180 0.7934 0.9807 0.039 Uiso 1 1 calc R . . H19 H 0.306(8) 0.660(3) 0.682(3) 0.111(17) Uiso 1 1 d . . . H20 H 0.301(4) 0.6889(14) 0.9174(18) 0.027(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0189(4) 0.0242(4) 0.0270(4) -0.0011(3) 0.0041(3) 0.0005(3) O1 0.0210(10) 0.0332(12) 0.0441(12) -0.0057(9) 0.0115(9) 0.0009(9) O2 0.0449(13) 0.0380(13) 0.0358(12) -0.0058(10) 0.0157(10) 0.0088(10) C1 0.0209(14) 0.0219(15) 0.0246(14) -0.0015(11) 0.0052(11) 0.0024(11) C2 0.0325(16) 0.0295(17) 0.0283(15) -0.0038(12) 0.0056(13) 0.0018(13) C3 0.0251(15) 0.0296(16) 0.0185(13) -0.0008(11) -0.0004(11) -0.0029(12) C4 0.0221(14) 0.0339(17) 0.0265(15) 0.0005(12) 0.0023(11) -0.0025(13) C5 0.0245(15) 0.0359(18) 0.0393(17) 0.0007(13) 0.0016(13) 0.0062(13) C6 0.0380(17) 0.0264(16) 0.0375(17) 0.0051(13) -0.0024(14) -0.0022(14) C7 0.0355(17) 0.0399(19) 0.0250(15) 0.0033(13) 0.0065(13) -0.0116(14) C8 0.0275(15) 0.0388(18) 0.0226(14) -0.0017(13) 0.0040(12) 0.0003(13) C9 0.0236(14) 0.0259(16) 0.0293(15) 0.0000(12) 0.0058(12) -0.0009(12) C10 0.0345(17) 0.0283(17) 0.0385(17) -0.0012(13) 0.0070(14) -0.0060(13) C11 0.0344(16) 0.0345(17) 0.0309(16) 0.0034(13) 0.0098(13) -0.0037(14) C12 0.0332(17) 0.0237(16) 0.0473(19) 0.0002(13) 0.0068(14) 0.0037(13) C13 0.0213(14) 0.0266(15) 0.0246(14) -0.0005(11) 0.0028(11) -0.0017(11) C14 0.0251(15) 0.0310(17) 0.0370(16) -0.0021(13) 0.0078(13) -0.0038(13) C15 0.0361(17) 0.0272(17) 0.0418(18) -0.0011(13) 0.0082(14) -0.0078(14) C16 0.0387(18) 0.0262(17) 0.0396(18) -0.0073(13) 0.0051(14) -0.0004(13) C17 0.0342(17) 0.0336(18) 0.054(2) -0.0119(15) 0.0166(15) 0.0005(14) C18 0.0295(15) 0.0313(17) 0.0399(17) -0.0061(13) 0.0123(13) -0.0050(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4992(19) . ? P1 C13 1.814(3) . ? P1 C1 1.832(3) . ? P1 H20 1.36(3) . ? O2 C2 1.438(3) . ? O2 H19 1.07(5) . ? C1 C2 1.559(4) . ? C1 C9 1.570(4) . ? C1 H1 1.0000 . ? C2 C3 1.522(4) . ? C2 H2 1.0000 . ? C3 C8 1.387(4) . ? C3 C4 1.401(4) . ? C4 C5 1.373(4) . ? C4 H4 0.9500 . ? C5 C6 1.383(4) . ? C5 H5 0.9500 . ? C6 C7 1.375(4) . ? C6 H6 0.9500 . ? C7 C8 1.392(4) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C12 1.532(4) . ? C9 C10 1.536(4) . ? C9 C11 1.538(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C14 1.529(4) . ? C13 C18 1.532(4) . ? C13 H13 1.0000 . ? C14 C15 1.525(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.519(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.528(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.525(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C13 114.49(12) . . ? O1 P1 C1 111.63(12) . . ? C13 P1 C1 109.70(12) . . ? O1 P1 H20 112.2(11) . . ? C13 P1 H20 102.2(11) . . ? C1 P1 H20 106.0(11) . . ? C2 O2 H19 105(3) . . ? C2 C1 C9 115.4(2) . . ? C2 C1 P1 108.77(18) . . ? C9 C1 P1 113.69(18) . . ? C2 C1 H1 106.1 . . ? C9 C1 H1 106.1 . . ? P1 C1 H1 106.1 . . ? O2 C2 C3 112.7(2) . . ? O2 C2 C1 111.8(2) . . ? C3 C2 C1 111.4(2) . . ? O2 C2 H2 106.8 . . ? C3 C2 H2 106.8 . . ? C1 C2 H2 106.8 . . ? C8 C3 C4 118.4(3) . . ? C8 C3 C2 122.2(3) . . ? C4 C3 C2 119.4(2) . . ? C5 C4 C3 120.6(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C7 C6 C5 119.5(3) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C8 120.5(3) . . ? C6 C7 H7 119.7 . . ? C8 C7 H7 119.7 . . ? C3 C8 C7 120.3(3) . . ? C3 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C12 C9 C10 108.5(2) . . ? C12 C9 C11 109.4(2) . . ? C10 C9 C11 107.5(2) . . ? C12 C9 C1 113.3(2) . . ? C10 C9 C1 110.5(2) . . ? C11 C9 C1 107.5(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C14 C13 C18 110.7(2) . . ? C14 C13 P1 110.69(18) . . ? C18 C13 P1 111.88(19) . . ? C14 C13 H13 107.8 . . ? C18 C13 H13 107.8 . . ? P1 C13 H13 107.8 . . ? C15 C14 C13 109.7(2) . . ? C15 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? C15 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C16 C15 C14 111.4(2) . . ? C16 C15 H15A 109.3 . . ? C14 C15 H15A 109.3 . . ? C16 C15 H15B 109.3 . . ? C14 C15 H15B 109.3 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 111.5(2) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C16 111.9(2) . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C17 C18 C13 110.4(2) . . ? C17 C18 H18A 109.6 . . ? C13 C18 H18A 109.6 . . ? C17 C18 H18B 109.6 . . ? C13 C18 H18B 109.6 . . ? H18A C18 H18B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.92 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.355 _refine_diff_density_min -0.409 _refine_diff_density_rms 0.059