# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Bluemel, Janet' _publ_contact_author_email bluemel@tamu.edu _publ_section_title ; Synthesis, Purification, and Characterization of Phosphine Oxides and their Hydrogen Peroxide Adducts ; _publ_author_name J.Bluemel # Attachment 'jbb.cif' data_jbb1 _database_code_depnum_ccdc_archive 'CCDC 790886' #TrackingRef 'jbb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H27 O P' _chemical_formula_weight 218.31 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 9.326(6) _cell_length_b 15.281(10) _cell_length_c 10.136(7) _cell_angle_alpha 90.00 _cell_angle_beta 100.548(15) _cell_angle_gamma 90.00 _cell_volume 1420.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 1310 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.60 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.021 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9752 _exptl_absorpt_correction_T_max 0.9883 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2006)' _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 'APEX II' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 15057 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0458 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.61 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0 _reflns_number_total 3264 _reflns_number_gt 2328 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (BRUKER-NONIUS, 2003)' _computing_cell_refinement ; APEX-II(BRUKER-NONIUS, 2003) ; _computing_data_reduction APEX-II _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0851P)^2^+1.1507P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3264 _refine_ls_number_parameters 130 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0885 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1788 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 0.51554(6) 0.25411(3) 0.40723(6) 0.0240(2) Uani 1 1 d . . . O1 O 0.51421(18) 0.25888(10) 0.55368(17) 0.0298(4) Uani 1 1 d . . . C1 C 0.6861(2) 0.28806(14) 0.3650(2) 0.0288(5) Uani 1 1 d . . . H1A H 0.6885 0.2704 0.2715 0.035 Uiso 1 1 calc R . . H1B H 0.6925 0.3527 0.3696 0.035 Uiso 1 1 calc R . . C2 C 0.8175(3) 0.24925(14) 0.4574(2) 0.0294(5) Uani 1 1 d . . . H2A H 0.8087 0.2613 0.5516 0.035 Uiso 1 1 calc R . . H2B H 0.8163 0.1849 0.4453 0.035 Uiso 1 1 calc R . . C3 C 0.9628(3) 0.28440(19) 0.4335(3) 0.0380(6) Uani 1 1 d . . . H3A H 0.9782 0.2657 0.3436 0.046 Uiso 1 1 calc R . . H3B H 0.9604 0.3492 0.4348 0.046 Uiso 1 1 calc R . . C4 C 1.0888(3) 0.2525(2) 0.5385(3) 0.0514(8) Uani 1 1 d . . . H4A H 1.0745 0.2714 0.6276 0.077 Uiso 1 1 calc R . . H4B H 1.1802 0.2770 0.5201 0.077 Uiso 1 1 calc R . . H4C H 1.0932 0.1885 0.5359 0.077 Uiso 1 1 calc R . . C5 C 0.4824(3) 0.14554(14) 0.3403(2) 0.0292(5) Uani 1 1 d . . . H5A H 0.4741 0.1478 0.2416 0.035 Uiso 1 1 calc R . . H5B H 0.5669 0.1080 0.3766 0.035 Uiso 1 1 calc R . . C6 C 0.3450(3) 0.10445(14) 0.3733(2) 0.0318(5) Uani 1 1 d . . . H6A H 0.3516 0.1046 0.4719 0.038 Uiso 1 1 calc R . . H6B H 0.2602 0.1410 0.3339 0.038 Uiso 1 1 calc R . . C7 C 0.3184(3) 0.01152(16) 0.3225(3) 0.0410(6) Uani 1 1 d . . . H7A H 0.3160 0.0106 0.2244 0.049 Uiso 1 1 calc R . . H7B H 0.4004 -0.0259 0.3653 0.049 Uiso 1 1 calc R . . C8 C 0.1778(3) -0.02582(18) 0.3510(3) 0.0502(8) Uani 1 1 d . . . H8A H 0.1791 -0.0246 0.4479 0.075 Uiso 1 1 calc R . . H8B H 0.1670 -0.0864 0.3189 0.075 Uiso 1 1 calc R . . H8C H 0.0956 0.0092 0.3049 0.075 Uiso 1 1 calc R . . C9 C 0.3793(2) 0.32221(14) 0.3085(2) 0.0275(5) Uani 1 1 d . . . H9A H 0.4032 0.3289 0.2178 0.033 Uiso 1 1 calc R . . H9B H 0.2838 0.2922 0.2984 0.033 Uiso 1 1 calc R . . C10 C 0.3649(3) 0.41281(14) 0.3672(2) 0.0296(5) Uani 1 1 d . . . H10A H 0.3424 0.4066 0.4585 0.036 Uiso 1 1 calc R . . H10B H 0.4592 0.4439 0.3752 0.036 Uiso 1 1 calc R . . C11 C 0.2472(3) 0.46678(16) 0.2825(3) 0.0400(6) Uani 1 1 d . . . H11A H 0.1553 0.4328 0.2666 0.048 Uiso 1 1 calc R . . H11B H 0.2750 0.4779 0.1943 0.048 Uiso 1 1 calc R . . C12 C 0.2205(3) 0.55382(17) 0.3463(3) 0.0488(7) Uani 1 1 d . . . H12A H 0.1880 0.5433 0.4315 0.073 Uiso 1 1 calc R . . H12B H 0.1452 0.5865 0.2857 0.073 Uiso 1 1 calc R . . H12C H 0.3111 0.5878 0.3627 0.073 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 0.0277(3) 0.0190(3) 0.0251(3) -0.0003(2) 0.0042(2) -0.0009(2) O1 0.0334(9) 0.0291(8) 0.0270(9) 0.0000(6) 0.0055(7) -0.0023(6) C1 0.0337(12) 0.0214(10) 0.0307(12) 0.0023(8) 0.0042(9) -0.0017(9) C2 0.0287(12) 0.0257(11) 0.0336(12) 0.0031(9) 0.0051(9) 0.0014(9) C3 0.0320(13) 0.0421(14) 0.0402(14) 0.0053(11) 0.0074(10) 0.0005(11) C4 0.0289(14) 0.076(2) 0.0488(18) 0.0112(14) 0.0066(12) 0.0062(13) C5 0.0342(12) 0.0191(10) 0.0349(13) 0.0012(8) 0.0078(9) 0.0020(9) C6 0.0374(13) 0.0211(11) 0.0365(13) -0.0009(9) 0.0058(10) -0.0051(9) C7 0.0526(17) 0.0207(11) 0.0508(16) -0.0053(10) 0.0121(13) -0.0059(11) C8 0.0550(18) 0.0299(13) 0.065(2) -0.0055(12) 0.0082(15) -0.0174(12) C9 0.0318(12) 0.0188(10) 0.0308(12) -0.0035(8) 0.0033(9) -0.0018(8) C10 0.0344(12) 0.0202(10) 0.0332(12) -0.0045(9) 0.0035(9) 0.0013(9) C11 0.0451(15) 0.0210(11) 0.0516(16) -0.0052(10) 0.0029(12) 0.0042(10) C12 0.0515(17) 0.0241(12) 0.069(2) -0.0086(12) 0.0072(14) 0.0067(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 1.489(2) . ? P1 C1 1.797(3) . ? P1 C5 1.798(2) . ? P1 C9 1.798(2) . ? C1 C2 1.520(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.518(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.514(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 C6 1.518(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.516(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.506(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 C10 1.522(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.509(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.519(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? 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 113.10(10) . . ? O1 P1 C5 112.90(10) . . ? C1 P1 C5 105.98(11) . . ? O1 P1 C9 113.11(10) . . ? C1 P1 C9 105.46(11) . . ? C5 P1 C9 105.61(11) . . ? C2 C1 P1 112.94(16) . . ? C2 C1 H1A 109.0 . . ? P1 C1 H1A 109.0 . . ? C2 C1 H1B 109.0 . . ? P1 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 114.0(2) . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2B 108.8 . . ? C1 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? C4 C3 C2 112.0(2) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 H4A 109.5 . . ? C3 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C3 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C6 C5 P1 113.11(16) . . ? C6 C5 H5A 109.0 . . ? P1 C5 H5A 109.0 . . ? C6 C5 H5B 109.0 . . ? P1 C5 H5B 109.0 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C5 113.9(2) . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C6 112.6(2) . . ? C8 C7 H7A 109.1 . . ? C6 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.8 . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 P1 114.40(16) . . ? C10 C9 H9A 108.7 . . ? P1 C9 H9A 108.7 . . ? C10 C9 H9B 108.7 . . ? P1 C9 H9B 108.7 . . ? H9A C9 H9B 107.6 . . ? C11 C10 C9 112.47(19) . . ? C11 C10 H10A 109.1 . . ? C9 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C9 C10 H10B 109.1 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12 113.3(2) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 P1 C1 C2 45.38(19) . . . . ? C5 P1 C1 C2 -78.83(19) . . . . ? C9 P1 C1 C2 169.48(16) . . . . ? P1 C1 C2 C3 -173.78(17) . . . . ? C1 C2 C3 C4 172.9(2) . . . . ? O1 P1 C5 C6 52.7(2) . . . . ? C1 P1 C5 C6 177.02(17) . . . . ? C9 P1 C5 C6 -71.4(2) . . . . ? P1 C5 C6 C7 -177.70(18) . . . . ? C5 C6 C7 C8 -177.3(2) . . . . ? O1 P1 C9 C10 42.9(2) . . . . ? C1 P1 C9 C10 -81.19(19) . . . . ? C5 P1 C9 C10 166.86(17) . . . . ? P1 C9 C10 C11 -178.78(18) . . . . ? C9 C10 C11 C12 174.2(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.652 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.080 # Attachment 'jbb.cif' data_jbb2 _database_code_depnum_ccdc_archive 'CCDC 845791' #TrackingRef 'jbb.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H35 O3 P' _chemical_formula_weight 330.43 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 8.579(2) _cell_length_b 9.584(3) _cell_length_c 12.260(3) _cell_angle_alpha 95.445(3) _cell_angle_beta 97.065(3) _cell_angle_gamma 112.824(3) _cell_volume 910.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 982 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 27.27 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.205 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 364 _exptl_absorpt_coefficient_mu 0.162 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9516 _exptl_absorpt_correction_T_max 0.9730 _exptl_absorpt_process_details 'SADABS; (Sheldrick, 2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'APEX II' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10409 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 27.48 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0 _reflns_number_total 4067 _reflns_number_gt 3603 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX-II (BRUKER-NONIUS, 2003)' _computing_cell_refinement ; APEX-II(BRUKER-NONIUS, 2003) ; _computing_data_reduction APEX-II _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'X-SEED (Barbour, 2001)' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0444P)^2^+0.2874P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4067 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0376 _refine_ls_R_factor_gt 0.0327 _refine_ls_wR_factor_ref 0.0880 _refine_ls_wR_factor_gt 0.0843 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 0.09728(3) 0.26319(3) 0.30413(2) 0.01303(9) Uani 1 1 d . . . O1 O 0.23767(10) 0.32792(9) 0.40461(7) 0.01775(18) Uani 1 1 d . . . O20 O 0.56582(12) 0.33427(11) 0.42804(9) 0.0330(2) Uani 1 1 d . . . H20 H 0.4619 0.3370 0.4218 0.050 Uiso 1 1 d R . . O21 O 0.67169(12) 0.47890(12) 0.39673(8) 0.0367(3) Uani 1 1 d . . . H21 H 0.7071 0.5392 0.4631 0.055 Uiso 1 1 d R . . C1 C 0.17604(14) 0.20601(12) 0.18389(9) 0.0142(2) Uani 1 1 d . . . H1 H 0.0794 0.1670 0.1191 0.017 Uiso 1 1 calc R . . C2 C 0.23192(15) 0.07491(13) 0.20398(10) 0.0175(2) Uani 1 1 d . . . H2A H 0.3252 0.1098 0.2694 0.021 Uiso 1 1 calc R . . H2B H 0.1338 -0.0128 0.2203 0.021 Uiso 1 1 calc R . . C3 C 0.29445(16) 0.02308(13) 0.10284(10) 0.0209(2) Uani 1 1 d . . . H3A H 0.3364 -0.0565 0.1200 0.025 Uiso 1 1 calc R . . H3B H 0.1974 -0.0229 0.0396 0.025 Uiso 1 1 calc R . . C4 C 0.43825(15) 0.15664(14) 0.06977(11) 0.0216(3) Uani 1 1 d . . . H4A H 0.5405 0.1948 0.1294 0.026 Uiso 1 1 calc R . . H4B H 0.4704 0.1209 0.0010 0.026 Uiso 1 1 calc R . . C5 C 0.38298(15) 0.28657(13) 0.05028(10) 0.0182(2) Uani 1 1 d . . . H5A H 0.2873 0.2510 -0.0138 0.022 Uiso 1 1 calc R . . H5B H 0.4801 0.3734 0.0320 0.022 Uiso 1 1 calc R . . C6 C 0.32533(14) 0.34072(13) 0.15324(9) 0.0162(2) Uani 1 1 d . . . H6A H 0.2878 0.4236 0.1382 0.019 Uiso 1 1 calc R . . H6B H 0.4228 0.3822 0.2163 0.019 Uiso 1 1 calc R . . C7 C -0.07482(14) 0.09161(12) 0.33003(9) 0.0145(2) Uani 1 1 d . . . H7 H -0.0196 0.0214 0.3521 0.017 Uiso 1 1 calc R . . C8 C -0.15123(16) 0.12777(14) 0.43054(10) 0.0218(3) Uani 1 1 d . . . H8A H -0.0578 0.1819 0.4950 0.026 Uiso 1 1 calc R . . H8B H -0.2094 0.1961 0.4128 0.026 Uiso 1 1 calc R . . C9 C -0.27983(16) -0.01951(15) 0.46051(10) 0.0237(3) Uani 1 1 d . . . H9A H -0.2188 -0.0829 0.4857 0.028 Uiso 1 1 calc R . . H9B H -0.3319 0.0066 0.5228 0.028 Uiso 1 1 calc R . . C10 C -0.42080(16) -0.11134(15) 0.36200(11) 0.0251(3) Uani 1 1 d . . . H10A H -0.4897 -0.0524 0.3417 0.030 Uiso 1 1 calc R . . H10B H -0.4980 -0.2084 0.3831 0.030 Uiso 1 1 calc R . . C11 C -0.34537(16) -0.14695(14) 0.26196(10) 0.0239(3) Uani 1 1 d . . . H11A H -0.4392 -0.2019 0.1978 0.029 Uiso 1 1 calc R . . H11B H -0.2864 -0.2147 0.2797 0.029 Uiso 1 1 calc R . . C12 C -0.21784(15) 0.00013(13) 0.23072(9) 0.0188(2) Uani 1 1 d . . . H12A H -0.2790 0.0637 0.2064 0.023 Uiso 1 1 calc R . . H12B H -0.1668 -0.0261 0.1679 0.023 Uiso 1 1 calc R . . C13 C 0.00614(14) 0.39989(12) 0.26887(9) 0.0146(2) Uani 1 1 d . . . H13 H -0.0892 0.3847 0.3121 0.018 Uiso 1 1 calc R . . C14 C 0.13925(15) 0.56576(13) 0.30767(10) 0.0186(2) Uani 1 1 d . . . H14A H 0.1819 0.5806 0.3885 0.022 Uiso 1 1 calc R . . H14B H 0.2382 0.5849 0.2685 0.022 Uiso 1 1 calc R . . C15 C 0.05933(16) 0.67946(13) 0.28369(10) 0.0209(2) Uani 1 1 d . . . H15A H -0.0319 0.6670 0.3289 0.025 Uiso 1 1 calc R . . H15B H 0.1483 0.7852 0.3057 0.025 Uiso 1 1 calc R . . C16 C -0.01688(16) 0.65563(13) 0.16116(10) 0.0214(3) Uani 1 1 d . . . H16A H 0.0755 0.6756 0.1161 0.026 Uiso 1 1 calc R . . H16B H -0.0706 0.7288 0.1488 0.026 Uiso 1 1 calc R . . C17 C -0.15126(15) 0.49205(13) 0.12445(10) 0.0184(2) Uani 1 1 d . . . H17A H -0.1977 0.4773 0.0442 0.022 Uiso 1 1 calc R . . H17B H -0.2474 0.4744 0.1660 0.022 Uiso 1 1 calc R . . C18 C -0.07284(14) 0.37635(13) 0.14543(9) 0.0158(2) Uani 1 1 d . . . H18A H 0.0171 0.3885 0.0992 0.019 Uiso 1 1 calc R . . H18B H -0.1628 0.2710 0.1235 0.019 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 0.01256(14) 0.01257(14) 0.01351(15) 0.00206(10) 0.00162(10) 0.00481(11) O1 0.0160(4) 0.0183(4) 0.0172(4) 0.0018(3) -0.0008(3) 0.0063(3) O20 0.0231(5) 0.0324(5) 0.0410(6) -0.0032(4) -0.0022(4) 0.0127(4) O21 0.0289(5) 0.0463(6) 0.0234(5) -0.0038(4) 0.0060(4) 0.0047(5) C1 0.0132(5) 0.0137(5) 0.0158(5) 0.0021(4) 0.0030(4) 0.0054(4) C2 0.0189(5) 0.0142(5) 0.0211(6) 0.0046(4) 0.0060(4) 0.0074(4) C3 0.0218(6) 0.0174(6) 0.0261(6) 0.0022(5) 0.0075(5) 0.0099(5) C4 0.0197(6) 0.0231(6) 0.0268(6) 0.0061(5) 0.0100(5) 0.0117(5) C5 0.0172(5) 0.0197(6) 0.0198(6) 0.0057(4) 0.0063(4) 0.0081(4) C6 0.0147(5) 0.0155(5) 0.0189(5) 0.0043(4) 0.0039(4) 0.0059(4) C7 0.0145(5) 0.0142(5) 0.0147(5) 0.0032(4) 0.0034(4) 0.0052(4) C8 0.0221(6) 0.0218(6) 0.0181(6) 0.0010(5) 0.0079(5) 0.0045(5) C9 0.0217(6) 0.0272(6) 0.0191(6) 0.0060(5) 0.0077(5) 0.0047(5) C10 0.0174(6) 0.0288(7) 0.0239(6) 0.0083(5) 0.0050(5) 0.0025(5) C11 0.0212(6) 0.0200(6) 0.0217(6) 0.0024(5) 0.0030(5) -0.0006(5) C12 0.0173(5) 0.0180(6) 0.0160(5) 0.0025(4) 0.0020(4) 0.0020(4) C13 0.0155(5) 0.0138(5) 0.0149(5) 0.0021(4) 0.0025(4) 0.0064(4) C14 0.0207(6) 0.0144(5) 0.0178(5) 0.0002(4) -0.0022(4) 0.0063(4) C15 0.0267(6) 0.0140(5) 0.0208(6) 0.0006(4) -0.0001(5) 0.0087(5) C16 0.0240(6) 0.0159(6) 0.0232(6) 0.0048(4) -0.0004(5) 0.0080(5) C17 0.0169(5) 0.0183(6) 0.0196(6) 0.0037(4) -0.0002(4) 0.0074(5) C18 0.0148(5) 0.0155(5) 0.0158(5) 0.0018(4) 0.0008(4) 0.0056(4) _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 1.5045(9) . ? P1 C1 1.8190(12) . ? P1 C7 1.8209(12) . ? P1 C13 1.8258(12) . ? O20 O21 1.4504(15) . ? O20 H20 0.8961 . ? O21 H21 0.8952 . ? C1 C2 1.5383(15) . ? C1 C6 1.5415(15) . ? C1 H1 1.0000 . ? C2 C3 1.5250(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5235(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5229(16) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.5283(16) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C12 1.5336(15) . ? C7 C8 1.5370(16) . ? C7 H7 1.0000 . ? C8 C9 1.5279(16) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.5195(17) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.5253(18) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.5297(16) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C18 1.5378(15) . ? C13 C14 1.5401(15) . ? C13 H13 1.0000 . ? C14 C15 1.5280(16) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.5212(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5250(16) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.5292(15) . ? 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 C1 111.03(5) . . ? O1 P1 C7 109.92(5) . . ? C1 P1 C7 106.76(5) . . ? O1 P1 C13 112.04(5) . . ? C1 P1 C13 108.68(5) . . ? C7 P1 C13 108.24(5) . . ? O21 O20 H20 103.2 . . ? O20 O21 H21 100.4 . . ? C2 C1 C6 109.92(9) . . ? C2 C1 P1 110.59(7) . . ? C6 C1 P1 112.44(8) . . ? C2 C1 H1 107.9 . . ? C6 C1 H1 107.9 . . ? P1 C1 H1 107.9 . . ? C3 C2 C1 111.25(9) . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C2 111.37(10) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C5 C4 C3 111.09(10) . . ? C5 C4 H4A 109.4 . . ? C3 C4 H4A 109.4 . . ? C5 C4 H4B 109.4 . . ? C3 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 111.02(9) . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5B 109.4 . . ? C6 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C1 110.01(9) . . ? C5 C6 H6A 109.7 . . ? C1 C6 H6A 109.7 . . ? C5 C6 H6B 109.7 . . ? C1 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? C12 C7 C8 110.55(9) . . ? C12 C7 P1 116.48(8) . . ? C8 C7 P1 110.95(8) . . ? C12 C7 H7 106.0 . . ? C8 C7 H7 106.0 . . ? P1 C7 H7 106.0 . . ? C9 C8 C7 110.60(10) . . ? C9 C8 H8A 109.5 . . ? C7 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C10 C9 C8 111.57(10) . . ? C10 C9 H9A 109.3 . . ? C8 C9 H9A 109.3 . . ? C10 C9 H9B 109.3 . . ? C8 C9 H9B 109.3 . . ? H9A C9 H9B 108.0 . . ? C9 C10 C11 111.04(10) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C10 C11 C12 110.97(10) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C7 110.77(9) . . ? C11 C12 H12A 109.5 . . ? C7 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? C18 C13 C14 110.87(9) . . ? C18 C13 P1 114.44(7) . . ? C14 C13 P1 110.80(8) . . ? C18 C13 H13 106.8 . . ? C14 C13 H13 106.8 . . ? P1 C13 H13 106.8 . . ? C15 C14 C13 110.55(10) . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C14 111.59(10) . . ? 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 110.32(10) . . ? C15 C16 H16A 109.6 . . ? C17 C16 H16A 109.6 . . ? C15 C16 H16B 109.6 . . ? C17 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C16 C17 C18 110.71(9) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 C13 110.79(9) . . ? C17 C18 H18A 109.5 . . ? C13 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C13 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 P1 C1 C2 63.94(9) . . . . ? C7 P1 C1 C2 -55.86(9) . . . . ? C13 P1 C1 C2 -172.40(7) . . . . ? O1 P1 C1 C6 -59.36(9) . . . . ? C7 P1 C1 C6 -179.16(7) . . . . ? C13 P1 C1 C6 64.30(9) . . . . ? C6 C1 C2 C3 -56.57(12) . . . . ? P1 C1 C2 C3 178.68(8) . . . . ? C1 C2 C3 C4 55.41(13) . . . . ? C2 C3 C4 C5 -55.16(13) . . . . ? C3 C4 C5 C6 56.79(13) . . . . ? C4 C5 C6 C1 -58.15(12) . . . . ? C2 C1 C6 C5 57.66(12) . . . . ? P1 C1 C6 C5 -178.66(7) . . . . ? O1 P1 C7 C12 -172.68(8) . . . . ? C1 P1 C7 C12 -52.17(10) . . . . ? C13 P1 C7 C12 64.66(9) . . . . ? O1 P1 C7 C8 59.68(9) . . . . ? C1 P1 C7 C8 -179.81(8) . . . . ? C13 P1 C7 C8 -62.98(9) . . . . ? C12 C7 C8 C9 56.16(13) . . . . ? P1 C7 C8 C9 -173.04(8) . . . . ? C7 C8 C9 C10 -56.05(14) . . . . ? C8 C9 C10 C11 56.03(14) . . . . ? C9 C10 C11 C12 -56.10(14) . . . . ? C10 C11 C12 C7 56.63(13) . . . . ? C8 C7 C12 C11 -56.67(13) . . . . ? P1 C7 C12 C11 175.49(8) . . . . ? O1 P1 C13 C18 153.72(8) . . . . ? C1 P1 C13 C18 30.66(9) . . . . ? C7 P1 C13 C18 -84.92(9) . . . . ? O1 P1 C13 C14 27.47(9) . . . . ? C1 P1 C13 C14 -95.58(8) . . . . ? C7 P1 C13 C14 148.83(8) . . . . ? C18 C13 C14 C15 54.91(12) . . . . ? P1 C13 C14 C15 -176.89(8) . . . . ? C13 C14 C15 C16 -56.15(13) . . . . ? C14 C15 C16 C17 57.56(13) . . . . ? C15 C16 C17 C18 -57.78(13) . . . . ? C16 C17 C18 C13 57.22(12) . . . . ? C14 C13 C18 C17 -55.76(12) . . . . ? P1 C13 C18 C17 178.04(7) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.386 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.044