Supplementary Material (ESI) for Dalton Transactions This journal (c) The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 186 _publ_requested_journal 'Dalton Transactions' loop_ _publ_author_name 'Manners, I.' 'Lough, Alan' 'Rivard, Eric' _publ_contact_author_name 'Prof I Manners' _publ_contact_author_address ; Department of Chemistry University of Toronto 80 St. George Street Toronto M5S 1A1 CANADA ; _publ_contact_author_email 'IMANNERS@ALCHEMY.CHEM.UTORONTO.CA' _publ_section_title ; Synthesis, characterization and thermolysis of phosphinite-borane adducts: Investigation of an unusual thermally-induced phenol elimination reaction. ; data_k00259 _database_code_CSD 181265 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H5 H29 B O P' _chemical_formula_weight 308.23 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' 'B' 'B' 0.0013 0.0007 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 9.9490(12) _cell_length_b 15.6210(19) _cell_length_c 12.7660(11) _cell_angle_alpha 90.00 _cell_angle_beta 101.303(7) _cell_angle_gamma 90.00 _cell_volume 1945.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 17963 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 25.03 _exptl_crystal_description 'plate' _exptl_crystal_colour ? _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.052 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 680 _exptl_absorpt_coefficient_mu 0.139 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9835 _exptl_absorpt_correction_T_max 0.9917 _exptl_absorpt_process_details 'Denzo-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _diffrn_radiation_wavelength 0.71070 _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 '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 13449 _diffrn_reflns_av_R_equivalents 0.162 _diffrn_reflns_av_sigmaI/netI 0.0997 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 22.50 _reflns_number_total 2533 _reflns_number_gt 1445 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2001)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_structure_refinement 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_molecular_graphics 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_publication_material 'SHELXTL V5.1 (Sheldrick, 1999)' _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^)+(0.0839P)^2^+] 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 'none' _refine_ls_extinction_expression 'none' _refine_ls_number_reflns 2533 _refine_ls_number_parameters 224 _refine_ls_number_restraints 25 _refine_ls_R_factor_all 0.1274 _refine_ls_R_factor_gt 0.0654 _refine_ls_wR_factor_ref 0.1833 _refine_ls_wR_factor_gt 0.1548 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.010 _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 0.86582(12) 0.25019(8) 0.64726(8) 0.0390(4) Uani 1 1 d . . . H1P H 0.810(4) 0.326(2) 0.620(2) 0.035(10) Uiso 1 1 d . . . H2P H 0.757(4) 0.197(2) 0.600(3) 0.052(12) Uiso 1 1 d . . . O1 O 0.8827(3) 0.24253(16) 0.77394(19) 0.0343(7) Uani 1 1 d . . . C1 C 0.7701(4) 0.2478(3) 0.8268(3) 0.0289(10) Uani 1 1 d . . . C2 C 0.7204(4) 0.3279(3) 0.8493(3) 0.0300(11) Uani 1 1 d . . . C3 C 0.6006(4) 0.3287(3) 0.8919(3) 0.0326(11) Uani 1 1 d . . . H3A H 0.5615 0.3824 0.9043 0.039 Uiso 1 1 calc R . . C4 C 0.5368(4) 0.2543(3) 0.9167(3) 0.0286(10) Uani 1 1 d . A . C5 C 0.6002(4) 0.1770(3) 0.9016(3) 0.0310(11) Uani 1 1 d . . . H5A H 0.5606 0.1259 0.9221 0.037 Uiso 1 1 calc R . . C6 C 0.7174(4) 0.1698(3) 0.8586(3) 0.0284(11) Uani 1 1 d . . . C7 C 0.7898(5) 0.4171(3) 0.8398(3) 0.0368(12) Uani 1 1 d . . . C8 C 0.6970(5) 0.4703(3) 0.7527(3) 0.0558(15) Uani 1 1 d . . . H8A H 0.7395 0.5262 0.7462 0.084 Uiso 1 1 calc R . . H8B H 0.6074 0.4786 0.7722 0.084 Uiso 1 1 calc R . . H8C H 0.6851 0.4401 0.6843 0.084 Uiso 1 1 calc R . . C9 C 0.9354(5) 0.4161(3) 0.8177(3) 0.0514(14) Uani 1 1 d . . . H9A H 0.9679 0.4751 0.8139 0.077 Uiso 1 1 calc R . . H9B H 0.9354 0.3871 0.7497 0.077 Uiso 1 1 calc R . . H9C H 0.9962 0.3856 0.8754 0.077 Uiso 1 1 calc R . . C10 C 0.8020(5) 0.4635(3) 0.9480(3) 0.0509(14) Uani 1 1 d . . . H10A H 0.8454 0.5194 0.9442 0.076 Uiso 1 1 calc R . . H10B H 0.8579 0.4290 1.0044 0.076 Uiso 1 1 calc R . . H10C H 0.7105 0.4715 0.9640 0.076 Uiso 1 1 calc R . . C11 C 0.4076(4) 0.2559(2) 0.9650(3) 0.0358(10) Uani 1 1 d D . . C12 C 0.3486(7) 0.3453(3) 0.9690(6) 0.088(3) Uani 0.829(7) 1 d PD A 1 H12A H 0.4153 0.3817 1.0153 0.132 Uiso 0.829(7) 1 calc PR A 1 H12B H 0.2641 0.3423 0.9975 0.132 Uiso 0.829(7) 1 calc PR A 1 H12C H 0.3282 0.3695 0.8969 0.132 Uiso 0.829(7) 1 calc PR A 1 C13 C 0.4410(6) 0.2221(4) 1.0790(3) 0.061(2) Uani 0.829(7) 1 d PD A 1 H13A H 0.4957 0.1697 1.0812 0.092 Uiso 0.829(7) 1 calc PR A 1 H13B H 0.3557 0.2095 1.1035 0.092 Uiso 0.829(7) 1 calc PR A 1 H13C H 0.4932 0.2653 1.1258 0.092 Uiso 0.829(7) 1 calc PR A 1 C14 C 0.2992(5) 0.1972(4) 0.9017(4) 0.062(2) Uani 0.829(7) 1 d PD A 1 H14A H 0.2754 0.2172 0.8276 0.093 Uiso 0.829(7) 1 calc PR A 1 H14B H 0.2172 0.1980 0.9336 0.093 Uiso 0.829(7) 1 calc PR A 1 H14C H 0.3352 0.1387 0.9032 0.093 Uiso 0.829(7) 1 calc PR A 1 C12* C 0.3014(18) 0.3081(13) 0.8894(15) 0.053(9) Uiso 0.171(7) 1 d PD A 2 H12D H 0.3398 0.3643 0.8779 0.079 Uiso 0.171(7) 1 calc PR A 2 H12E H 0.2197 0.3155 0.9206 0.079 Uiso 0.171(7) 1 calc PR A 2 H12F H 0.2764 0.2781 0.8209 0.079 Uiso 0.171(7) 1 calc PR A 2 C13* C 0.438(2) 0.3028(13) 1.0714(10) 0.046(9) Uiso 0.171(7) 1 d PD A 2 H13D H 0.5208 0.2788 1.1162 0.068 Uiso 0.171(7) 1 calc PR A 2 H13E H 0.3605 0.2962 1.1077 0.068 Uiso 0.171(7) 1 calc PR A 2 H13F H 0.4525 0.3638 1.0590 0.068 Uiso 0.171(7) 1 calc PR A 2 C14* C 0.342(2) 0.1708(8) 0.9833(18) 0.075(12) Uiso 0.171(7) 1 d PD A 2 H14D H 0.3870 0.1246 0.9512 0.113 Uiso 0.171(7) 1 calc PR A 2 H14E H 0.2443 0.1722 0.9504 0.113 Uiso 0.171(7) 1 calc PR A 2 H14F H 0.3521 0.1605 1.0602 0.113 Uiso 0.171(7) 1 calc PR A 2 C15 C 0.7816(4) 0.0810(3) 0.8484(3) 0.0331(11) Uani 1 1 d . . . C16 C 0.7513(6) 0.0483(3) 0.7339(3) 0.0655(16) Uani 1 1 d . . . H16A H 0.7881 0.0887 0.6879 0.098 Uiso 1 1 calc R . . H16B H 0.6520 0.0431 0.7094 0.098 Uiso 1 1 calc R . . H16C H 0.7944 -0.0078 0.7308 0.098 Uiso 1 1 calc R . . C17 C 0.9373(5) 0.0824(3) 0.8905(4) 0.0598(15) Uani 1 1 d . . . H17A H 0.9796 0.1247 0.8505 0.090 Uiso 1 1 calc R . . H17B H 0.9755 0.0257 0.8816 0.090 Uiso 1 1 calc R . . H17C H 0.9560 0.0977 0.9664 0.090 Uiso 1 1 calc R . . C18 C 0.7255(5) 0.0141(3) 0.9161(4) 0.0579(15) Uani 1 1 d . . . H18A H 0.7433 0.0325 0.9909 0.087 Uiso 1 1 calc R . . H18B H 0.7707 -0.0410 0.9103 0.087 Uiso 1 1 calc R . . H18C H 0.6265 0.0079 0.8904 0.087 Uiso 1 1 calc R . . B1 B 1.0355(7) 0.2333(5) 0.6061(5) 0.0501(17) Uani 1 1 d . . . H1B H 0.997(5) 0.238(2) 0.517(3) 0.060(13) Uiso 1 1 d . . . H2B H 1.065(5) 0.171(3) 0.633(3) 0.057(14) Uiso 1 1 d . . . H3B H 1.102(5) 0.285(3) 0.639(3) 0.069(16) 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 0.0386(8) 0.0454(8) 0.0344(7) 0.0002(6) 0.0106(5) 0.0002(8) O1 0.0296(17) 0.0416(18) 0.0334(15) 0.0033(14) 0.0104(12) 0.0026(16) C1 0.023(2) 0.033(2) 0.031(2) -0.002(2) 0.0068(17) -0.001(2) C2 0.032(3) 0.030(3) 0.029(2) 0.0030(19) 0.007(2) -0.003(2) C3 0.033(3) 0.029(3) 0.036(3) 0.000(2) 0.009(2) 0.002(2) C4 0.027(2) 0.029(2) 0.031(2) 0.001(2) 0.0073(18) -0.001(2) C5 0.034(3) 0.028(3) 0.032(2) 0.0017(19) 0.009(2) -0.004(2) C6 0.029(3) 0.029(3) 0.029(2) -0.0041(19) 0.008(2) 0.000(2) C7 0.044(3) 0.025(3) 0.045(3) 0.005(2) 0.017(2) -0.006(2) C8 0.062(4) 0.039(3) 0.064(3) 0.021(3) 0.004(3) -0.004(3) C9 0.056(4) 0.046(3) 0.057(3) -0.002(2) 0.025(3) -0.015(3) C10 0.065(4) 0.038(3) 0.055(3) -0.010(2) 0.027(3) -0.017(3) C11 0.029(3) 0.033(3) 0.048(3) 0.002(2) 0.013(2) 0.001(2) C12 0.081(6) 0.042(4) 0.166(8) 0.001(5) 0.086(6) 0.006(4) C13 0.041(4) 0.088(6) 0.062(4) 0.000(3) 0.028(3) -0.002(3) C14 0.028(4) 0.087(5) 0.075(5) -0.020(4) 0.020(3) -0.018(4) C15 0.032(3) 0.029(3) 0.039(3) -0.002(2) 0.007(2) 0.000(2) C16 0.092(5) 0.047(3) 0.057(3) -0.017(3) 0.011(3) 0.014(3) C17 0.045(4) 0.040(3) 0.092(4) 0.004(3) 0.009(3) 0.011(3) C18 0.071(4) 0.032(3) 0.077(3) 0.008(3) 0.031(3) 0.012(3) B1 0.047(4) 0.065(5) 0.041(3) 0.005(3) 0.015(3) -0.001(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 H1P 1.33(4) . ? P1 H2P 1.40(4) . ? P1 O1 1.597(3) . ? P1 B1 1.882(6) . ? O1 C1 1.419(4) . ? C1 C2 1.397(5) . ? C1 C6 1.417(5) . ? C2 C3 1.403(5) . ? C2 C7 1.570(5) . ? C3 C4 1.390(5) . ? C4 C5 1.393(5) . ? C4 C11 1.531(5) . ? C5 C6 1.387(5) . ? C6 C15 1.544(5) . ? C7 C9 1.529(6) . ? C7 C8 1.542(6) . ? C7 C10 1.543(5) . ? C11 C12 1.520(4) . ? C11 C14* 1.520(4) . ? C11 C13* 1.521(4) . ? C11 C12* 1.521(4) . ? C11 C14 1.521(4) . ? C11 C13 1.522(4) . ? C15 C16 1.521(5) . ? C15 C18 1.530(5) . ? C15 C17 1.537(6) . ? B1 H2B 1.05(4) . ? B1 H3B 1.07(5) . ? B1 H1B 1.12(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 H1P P1 H2P 100(2) . . ? H1P P1 O1 106.5(13) . . ? H2P P1 O1 108.2(14) . . ? H1P P1 B1 114.0(14) . . ? H2P P1 B1 116.9(14) . . ? O1 P1 B1 110.5(2) . . ? C1 O1 P1 122.8(2) . . ? C2 C1 C6 123.1(3) . . ? C2 C1 O1 119.6(4) . . ? C6 C1 O1 117.2(3) . . ? C1 C2 C3 116.7(4) . . ? C1 C2 C7 126.9(4) . . ? C3 C2 C7 116.2(4) . . ? C4 C3 C2 122.7(4) . . ? C3 C4 C5 117.0(3) . . ? C3 C4 C11 122.3(4) . . ? C5 C4 C11 120.6(3) . . ? C6 C5 C4 124.3(4) . . ? C5 C6 C1 115.5(3) . . ? C5 C6 C15 120.1(4) . . ? C1 C6 C15 124.4(3) . . ? C9 C7 C8 109.1(3) . . ? C9 C7 C10 105.0(4) . . ? C8 C7 C10 108.9(4) . . ? C9 C7 C2 116.9(3) . . ? C8 C7 C2 108.9(4) . . ? C10 C7 C2 107.8(3) . . ? C12 C11 C14* 128.2(10) . . ? C12 C11 C13* 62.5(8) . . ? C14* C11 C13* 107.5(3) . . ? C12 C11 C12* 45.9(8) . . ? C14* C11 C12* 107.5(3) . . ? C13* C11 C12* 107.5(3) . . ? C12 C11 C14 109.5(5) . . ? C14* C11 C14 43.4(8) . . ? C13* C11 C14 139.6(8) . . ? C12* C11 C14 69.8(9) . . ? C12 C11 C13 107.5(3) . . ? C14* C11 C13 64.5(8) . . ? C13* C11 C13 49.1(8) . . ? C12* C11 C13 141.9(10) . . ? C14 C11 C13 107.3(3) . . ? C12 C11 C4 112.9(4) . . ? C14* C11 C4 117.9(10) . . ? C13* C11 C4 109.4(8) . . ? C12* C11 C4 106.6(9) . . ? C14 C11 C4 109.8(3) . . ? C13 C11 C4 109.6(3) . . ? C16 C15 C18 106.7(4) . . ? C16 C15 C17 109.7(4) . . ? C18 C15 C17 105.4(4) . . ? C16 C15 C6 112.0(3) . . ? C18 C15 C6 111.3(3) . . ? C17 C15 C6 111.3(3) . . ? H2B B1 H3B 117(4) . . ? H2B B1 H1B 114(3) . . ? H3B B1 H1B 114(3) . . ? H2B B1 P1 105(2) . . ? H3B B1 P1 108(3) . . ? H1B B1 P1 97(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 22.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.203 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.049 data_k00276 _database_code_CSD 181266 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H4 H34 B O P' _chemical_formula_weight 384.32 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' 'B' 'B' 0.0013 0.0007 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/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 18.0012(4) _cell_length_b 8.0595(2) _cell_length_c 18.4874(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.7360(10) _cell_angle_gamma 90.00 _cell_volume 2651.05(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 6321 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.48 _exptl_crystal_description 'needle' _exptl_crystal_colour ? _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 0.963 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 840 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9647 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details 'Denzo-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 23956 _diffrn_reflns_av_R_equivalents 0.067 _diffrn_reflns_av_sigmaI/netI 0.0635 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.66 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6062 _reflns_number_gt 4272 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Collect (Nonius BV, 1997-2001)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_structure_refinement 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_molecular_graphics 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_publication_material 'SHELXTL V5.1 (Sheldrick, 1999)' _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^)+(0.0924P)^2^+0.8393P] 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 6062 _refine_ls_number_parameters 259 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.1788 _refine_ls_wR_factor_gt 0.1651 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.055 _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 0.22864(3) 0.97779(8) 0.06156(3) 0.02976(17) Uani 1 1 d D . . H1P H 0.2422(13) 1.1476(13) 0.0599(12) 0.036 Uiso 1 1 d D . . O1 O 0.28981(7) 0.84983(18) 0.10259(7) 0.0245(3) Uani 1 1 d . . . C1 C 0.31642(10) 0.8756(3) 0.17788(10) 0.0225(4) Uani 1 1 d . . . C2 C 0.28386(10) 0.7810(3) 0.22937(10) 0.0228(4) Uani 1 1 d . . . C3 C 0.29892(11) 0.8357(3) 0.30195(10) 0.0254(4) Uani 1 1 d . . . H3A H 0.2765 0.7780 0.3379 0.030 Uiso 1 1 calc R . . C4 C 0.34513(11) 0.9703(3) 0.32406(10) 0.0235(4) Uani 1 1 d . . . C5 C 0.38288(11) 1.0427(3) 0.27211(10) 0.0240(4) Uani 1 1 d . . . H5A H 0.4179 1.1287 0.2873 0.029 Uiso 1 1 calc R . . C6 C 0.37183(11) 0.9953(2) 0.19815(10) 0.0223(4) Uani 1 1 d . . . C7 C 0.23776(11) 0.6196(3) 0.21443(11) 0.0268(4) Uani 1 1 d . . . C8 C 0.15964(12) 0.6383(3) 0.23762(13) 0.0384(5) Uani 1 1 d . . . H8A H 0.1652 0.6797 0.2880 0.058 Uiso 1 1 calc R . . H8B H 0.1344 0.5302 0.2347 0.058 Uiso 1 1 calc R . . H8C H 0.1296 0.7169 0.2049 0.058 Uiso 1 1 calc R . . C9 C 0.22725(14) 0.5542(3) 0.13574(12) 0.0370(5) Uani 1 1 d . . . H9A H 0.1997 0.6362 0.1029 0.055 Uiso 1 1 calc R . . H9B H 0.1988 0.4501 0.1329 0.055 Uiso 1 1 calc R . . H9C H 0.2765 0.5344 0.1210 0.055 Uiso 1 1 calc R . . C10 C 0.28169(13) 0.4838(3) 0.26267(12) 0.0336(5) Uani 1 1 d . . . H10A H 0.2895 0.5197 0.3139 0.050 Uiso 1 1 calc R . . H10B H 0.3305 0.4656 0.2466 0.050 Uiso 1 1 calc R . . H10C H 0.2528 0.3802 0.2580 0.050 Uiso 1 1 calc R . . C11 C 0.35424(12) 1.0300(3) 0.40375(10) 0.0279(5) Uani 1 1 d . . . C12 C 0.40787(15) 1.1771(3) 0.41778(12) 0.0424(6) Uani 1 1 d . . . H12A H 0.4575 1.1450 0.4069 0.064 Uiso 1 1 calc R . . H12B H 0.4121 1.2107 0.4692 0.064 Uiso 1 1 calc R . . H12C H 0.3885 1.2700 0.3862 0.064 Uiso 1 1 calc R . . C13 C 0.27676(14) 1.0828(4) 0.42128(13) 0.0427(6) Uani 1 1 d . . . H13A H 0.2418 0.9892 0.4127 0.064 Uiso 1 1 calc R . . H13B H 0.2576 1.1758 0.3897 0.064 Uiso 1 1 calc R . . H13C H 0.2815 1.1171 0.4726 0.064 Uiso 1 1 calc R . . C14 C 0.38489(14) 0.8888(3) 0.45561(11) 0.0364(5) Uani 1 1 d . . . H14A H 0.3512 0.7929 0.4475 0.055 Uiso 1 1 calc R . . H14B H 0.3880 0.9262 0.5064 0.055 Uiso 1 1 calc R . . H14C H 0.4351 0.8572 0.4460 0.055 Uiso 1 1 calc R . . C15 C 0.42533(11) 1.0734(3) 0.14884(10) 0.0237(4) Uani 1 1 d . . . C16 C 0.42309(12) 0.9911(3) 0.07341(11) 0.0309(5) Uani 1 1 d . . . H16A H 0.4582 1.0480 0.0462 0.046 Uiso 1 1 calc R . . H16B H 0.3721 0.9987 0.0461 0.046 Uiso 1 1 calc R . . H16C H 0.4375 0.8742 0.0799 0.046 Uiso 1 1 calc R . . C17 C 0.41124(12) 1.2594(3) 0.13879(11) 0.0298(5) Uani 1 1 d . . . H17A H 0.4454 1.3051 0.1073 0.045 Uiso 1 1 calc R . . H17B H 0.4201 1.3145 0.1866 0.045 Uiso 1 1 calc R . . H17C H 0.3591 1.2781 0.1160 0.045 Uiso 1 1 calc R . . C18 C 0.50687(12) 1.0491(3) 0.18872(12) 0.0352(5) Uani 1 1 d . . . H18A H 0.5423 1.0965 0.1590 0.053 Uiso 1 1 calc R . . H18B H 0.5171 0.9304 0.1960 0.053 Uiso 1 1 calc R . . H18C H 0.5127 1.1051 0.2363 0.053 Uiso 1 1 calc R . . C19 C 0.15000(12) 0.9934(3) 0.11076(12) 0.0338(5) Uani 1 1 d . . . C20 C 0.08072(14) 0.9247(4) 0.08060(16) 0.0498(7) Uani 1 1 d . . . H20A H 0.0757 0.8659 0.0356 0.060 Uiso 1 1 calc R . . C21 C 0.01985(15) 0.9435(5) 0.1169(2) 0.0672(9) Uani 1 1 d . . . H21A H -0.0276 0.8989 0.0965 0.081 Uiso 1 1 calc R . . C22 C 0.02747(17) 1.0276(5) 0.1836(2) 0.0727(11) Uani 1 1 d . . . H22A H -0.0148 1.0393 0.2083 0.087 Uiso 1 1 calc R . . C23 C 0.09570(17) 1.0939(4) 0.21388(17) 0.0563(8) Uani 1 1 d . . . H23A H 0.1004 1.1510 0.2593 0.068 Uiso 1 1 calc R . . C24 C 0.15746(13) 1.0772(3) 0.17798(13) 0.0376(5) Uani 1 1 d . . . H24A H 0.2047 1.1223 0.1988 0.045 Uiso 1 1 calc R . . B1 B 0.20647(19) 0.9337(5) -0.04004(15) 0.0466(7) Uani 1 1 d . . . H1B H 0.1803(15) 0.816(4) -0.0423(14) 0.052(8) Uiso 1 1 d . . . H2B H 0.263(2) 0.951(5) -0.0639(18) 0.089(12) Uiso 1 1 d . . . H3B H 0.164(2) 1.042(5) -0.0588(18) 0.090(12) 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 0.0315(3) 0.0350(3) 0.0215(3) 0.0002(2) 0.0000(2) 0.0052(2) O1 0.0271(7) 0.0295(8) 0.0164(6) -0.0019(6) 0.0017(5) 0.0019(6) C1 0.0239(9) 0.0267(11) 0.0167(8) -0.0025(7) 0.0026(7) 0.0019(8) C2 0.0216(9) 0.0245(11) 0.0220(9) -0.0006(8) 0.0029(7) 0.0007(8) C3 0.0283(10) 0.0274(11) 0.0207(9) 0.0020(8) 0.0047(8) -0.0014(9) C4 0.0265(10) 0.0244(11) 0.0192(9) 0.0009(8) 0.0023(7) 0.0006(8) C5 0.0257(9) 0.0249(11) 0.0212(9) -0.0013(8) 0.0028(7) -0.0021(8) C6 0.0239(9) 0.0235(11) 0.0198(9) -0.0004(7) 0.0039(7) 0.0015(8) C7 0.0285(10) 0.0268(11) 0.0249(10) -0.0023(8) 0.0031(8) -0.0036(9) C8 0.0281(11) 0.0401(14) 0.0477(13) -0.0008(11) 0.0080(10) -0.0079(10) C9 0.0477(13) 0.0307(13) 0.0309(11) -0.0055(9) 0.0006(10) -0.0098(11) C10 0.0411(12) 0.0264(12) 0.0324(11) -0.0012(9) 0.0029(9) -0.0035(10) C11 0.0342(11) 0.0308(12) 0.0189(9) -0.0026(8) 0.0048(8) -0.0042(9) C12 0.0649(16) 0.0405(14) 0.0221(10) -0.0072(10) 0.0075(10) -0.0192(12) C13 0.0484(14) 0.0511(16) 0.0303(11) -0.0087(11) 0.0114(10) 0.0075(12) C14 0.0494(13) 0.0381(14) 0.0203(10) 0.0025(9) 0.0010(9) -0.0013(11) C15 0.0243(9) 0.0264(11) 0.0213(9) 0.0012(8) 0.0063(7) 0.0000(8) C16 0.0334(11) 0.0373(13) 0.0241(10) -0.0008(9) 0.0111(8) 0.0004(9) C17 0.0332(11) 0.0284(12) 0.0289(10) 0.0031(9) 0.0084(9) -0.0015(9) C18 0.0271(10) 0.0471(15) 0.0319(11) 0.0065(10) 0.0058(9) 0.0014(10) C19 0.0274(10) 0.0371(13) 0.0357(11) 0.0011(10) 0.0004(9) 0.0061(9) C20 0.0323(12) 0.0564(18) 0.0569(16) 0.0034(13) -0.0058(11) 0.0025(12) C21 0.0265(13) 0.078(2) 0.096(3) 0.014(2) 0.0067(14) 0.0021(14) C22 0.0438(17) 0.081(3) 0.101(3) 0.019(2) 0.0377(18) 0.0182(16) C23 0.0605(18) 0.0554(19) 0.0593(17) 0.0023(14) 0.0287(14) 0.0174(15) C24 0.0395(12) 0.0346(13) 0.0401(12) -0.0021(10) 0.0108(10) 0.0059(10) B1 0.0540(18) 0.058(2) 0.0251(13) -0.0021(13) -0.0029(12) 0.0084(16) _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 H1P 1.391(10) . ? P1 O1 1.6117(15) . ? P1 C19 1.799(2) . ? P1 B1 1.894(3) . ? O1 C1 1.417(2) . ? C1 C6 1.397(3) . ? C1 C2 1.414(3) . ? C2 C3 1.399(3) . ? C2 C7 1.545(3) . ? C3 C4 1.390(3) . ? C4 C5 1.387(3) . ? C4 C11 1.535(3) . ? C5 C6 1.405(3) . ? C6 C15 1.556(3) . ? C7 C9 1.532(3) . ? C7 C8 1.538(3) . ? C7 C10 1.551(3) . ? C11 C12 1.526(3) . ? C11 C14 1.535(3) . ? C11 C13 1.539(3) . ? C15 C17 1.527(3) . ? C15 C16 1.539(3) . ? C15 C18 1.552(3) . ? C19 C20 1.401(3) . ? C19 C24 1.403(3) . ? C20 C21 1.378(4) . ? C21 C22 1.395(5) . ? C22 C23 1.378(5) . ? C23 C24 1.385(3) . ? B1 H1B 1.06(3) . ? B1 H2B 1.17(4) . ? B1 H3B 1.18(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 H1P P1 O1 122.0(9) . . ? H1P P1 C19 95.5(9) . . ? O1 P1 C19 109.90(9) . . ? H1P P1 B1 100.0(9) . . ? O1 P1 B1 111.89(12) . . ? C19 P1 B1 116.81(13) . . ? C1 O1 P1 118.27(12) . . ? C6 C1 C2 122.92(17) . . ? C6 C1 O1 119.05(16) . . ? C2 C1 O1 118.00(17) . . ? C3 C2 C1 115.86(18) . . ? C3 C2 C7 117.20(17) . . ? C1 C2 C7 126.84(17) . . ? C4 C3 C2 123.22(18) . . ? C5 C4 C3 117.33(17) . . ? C5 C4 C11 122.71(18) . . ? C3 C4 C11 119.94(17) . . ? C4 C5 C6 123.21(19) . . ? C1 C6 C5 116.03(17) . . ? C1 C6 C15 127.03(16) . . ? C5 C6 C15 116.84(17) . . ? C9 C7 C8 108.19(18) . . ? C9 C7 C2 116.42(17) . . ? C8 C7 C2 110.88(17) . . ? C9 C7 C10 106.37(18) . . ? C8 C7 C10 108.47(17) . . ? C2 C7 C10 106.16(16) . . ? C12 C11 C4 112.30(17) . . ? C12 C11 C14 108.16(19) . . ? C4 C11 C14 110.04(18) . . ? C12 C11 C13 108.6(2) . . ? C4 C11 C13 108.70(17) . . ? C14 C11 C13 108.94(18) . . ? C17 C15 C16 109.39(17) . . ? C17 C15 C18 108.03(18) . . ? C16 C15 C18 105.59(16) . . ? C17 C15 C6 111.24(16) . . ? C16 C15 C6 115.02(17) . . ? C18 C15 C6 107.18(16) . . ? C20 C19 C24 120.2(2) . . ? C20 C19 P1 119.51(19) . . ? C24 C19 P1 120.30(17) . . ? C21 C20 C19 119.2(3) . . ? C20 C21 C22 120.4(3) . . ? C23 C22 C21 120.6(3) . . ? C22 C23 C24 119.9(3) . . ? C23 C24 C19 119.7(2) . . ? H1B B1 H2B 120(2) . . ? H1B B1 H3B 113(2) . . ? H2B B1 H3B 111(2) . . ? H1B B1 P1 103.4(15) . . ? H2B B1 P1 106.7(17) . . ? H3B B1 P1 100.5(17) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.730 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.066 data_k00288a _database_code_CSD 181267 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H3 H39 B O P' _chemical_formula_weight 460.42 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' 'B' 'B' 0.0013 0.0007 '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' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pca21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 18.2421(6) _cell_length_b 12.3496(6) _cell_length_c 12.3712(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2787.0(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 2635 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 25.03 _exptl_crystal_description 'needle' _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.097 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.118 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9544 _exptl_absorpt_correction_T_max 0.9895 _exptl_absorpt_process_details 'Denzo-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 '\f scans \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14945 _diffrn_reflns_av_R_equivalents 0.099 _diffrn_reflns_av_sigmaI/netI 0.1403 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4606 _reflns_number_gt 2759 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2001)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_structure_refinement 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_molecular_graphics 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_publication_material 'SHELXTL V5.1 (Sheldrick, 1999)' _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^)+(0.0464P)^2^] 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 'none' _refine_ls_extinction_expression 'none' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.39(13) _refine_ls_number_reflns 4606 _refine_ls_number_parameters 321 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1309 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1234 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _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 0.04888(6) 0.33954(7) 0.04195(8) 0.0298(3) Uani 1 1 d . . . O1 O -0.01826(14) 0.30513(17) 0.12171(18) 0.0291(7) Uani 1 1 d . . . B1 B 0.0418(3) 0.2857(4) -0.1030(4) 0.0415(14) Uani 1 1 d . . . C1 C -0.0812(2) 0.2503(3) 0.0773(3) 0.0260(9) Uani 1 1 d . . . C2 C -0.0789(2) 0.1367(3) 0.0706(3) 0.0263(10) Uani 1 1 d . . . C3 C -0.1296(2) 0.0895(3) 0.0007(3) 0.0303(10) Uani 1 1 d . . . H3A H -0.1276 0.0134 -0.0098 0.036 Uiso 1 1 calc R . . C4 C -0.1830(2) 0.1481(3) -0.0546(3) 0.0293(10) Uani 1 1 d . . . C5 C -0.1896(2) 0.2568(3) -0.0277(3) 0.0317(10) Uani 1 1 d . . . H5A H -0.2296 0.2963 -0.0571 0.038 Uiso 1 1 calc R . . C6 C -0.1409(2) 0.3115(2) 0.0402(3) 0.0278(9) Uani 1 1 d . . . C7 C -0.0280(2) 0.0605(3) 0.1359(3) 0.0285(10) Uani 1 1 d . . . C8 C 0.0436(2) 0.0370(3) 0.0763(3) 0.0346(11) Uani 1 1 d . . . H8A H 0.0729 -0.0145 0.1183 0.052 Uiso 1 1 calc R . . H8B H 0.0711 0.1045 0.0670 0.052 Uiso 1 1 calc R . . H8C H 0.0326 0.0059 0.0052 0.052 Uiso 1 1 calc R . . C9 C -0.0121(2) 0.1055(3) 0.2490(3) 0.0385(11) Uani 1 1 d . . . H9A H 0.0162 0.0523 0.2904 0.058 Uiso 1 1 calc R . . H9B H -0.0584 0.1204 0.2863 0.058 Uiso 1 1 calc R . . H9C H 0.0162 0.1727 0.2426 0.058 Uiso 1 1 calc R . . C10 C -0.0661(3) -0.0504(3) 0.1538(3) 0.0428(12) Uani 1 1 d . . . H10A H -0.0384 -0.0925 0.2071 0.064 Uiso 1 1 calc R . . H10B H -0.0678 -0.0902 0.0853 0.064 Uiso 1 1 calc R . . H10C H -0.1161 -0.0386 0.1803 0.064 Uiso 1 1 calc R . . C11 C -0.2344(2) 0.0934(3) -0.1369(3) 0.0322(10) Uani 1 1 d . . . C12 C -0.2747(3) 0.1745(4) -0.2068(4) 0.0665(18) Uani 1 1 d . . . H12A H -0.3102 0.2142 -0.1626 0.100 Uiso 1 1 calc R . . H12B H -0.3005 0.1362 -0.2649 0.100 Uiso 1 1 calc R . . H12C H -0.2395 0.2255 -0.2383 0.100 Uiso 1 1 calc R . . C13 C -0.1885(3) 0.0244(5) -0.2144(4) 0.0850(19) Uani 1 1 d . . . H13A H -0.2207 -0.0092 -0.2682 0.127 Uiso 1 1 calc R . . H13B H -0.1629 -0.0321 -0.1735 0.127 Uiso 1 1 calc R . . H13C H -0.1525 0.0705 -0.2510 0.127 Uiso 1 1 calc R . . C14 C -0.2893(3) 0.0244(4) -0.0780(4) 0.0787(18) Uani 1 1 d . . . H14A H -0.3169 0.0694 -0.0270 0.118 Uiso 1 1 calc R . . H14B H -0.2637 -0.0330 -0.0384 0.118 Uiso 1 1 calc R . . H14C H -0.3232 -0.0082 -0.1303 0.118 Uiso 1 1 calc R . . C15 C -0.1606(2) 0.4292(3) 0.0710(3) 0.0306(10) Uani 1 1 d . . . C16 C -0.1284(2) 0.4650(3) 0.1788(3) 0.0429(12) Uani 1 1 d . . . H16A H -0.0748 0.4653 0.1742 0.064 Uiso 1 1 calc R . . H16B H -0.1440 0.4147 0.2357 0.064 Uiso 1 1 calc R . . H16C H -0.1458 0.5380 0.1961 0.064 Uiso 1 1 calc R . . C17 C -0.1369(3) 0.5064(3) -0.0191(4) 0.0473(12) Uani 1 1 d . . . H17A H -0.0839 0.5000 -0.0305 0.071 Uiso 1 1 calc R . . H17B H -0.1488 0.5810 0.0016 0.071 Uiso 1 1 calc R . . H17C H -0.1627 0.4878 -0.0860 0.071 Uiso 1 1 calc R . . C18 C -0.2441(2) 0.4409(3) 0.0833(4) 0.0465(12) Uani 1 1 d . . . H18A H -0.2558 0.5142 0.1081 0.070 Uiso 1 1 calc R . . H18B H -0.2619 0.3880 0.1362 0.070 Uiso 1 1 calc R . . H18C H -0.2677 0.4278 0.0134 0.070 Uiso 1 1 calc R . . C19 C 0.1297(2) 0.2997(3) 0.1158(3) 0.0296(10) Uani 1 1 d . . . C20 C 0.1383(3) 0.3131(3) 0.2276(3) 0.0390(11) Uani 1 1 d . . . H20A H 0.0983 0.3390 0.2695 0.047 Uiso 1 1 calc R . . C21 C 0.2033(3) 0.2893(3) 0.2772(3) 0.0444(12) Uani 1 1 d . . . H21A H 0.2082 0.2993 0.3530 0.053 Uiso 1 1 calc R . . C22 C 0.2623(3) 0.2506(3) 0.2172(4) 0.0442(12) Uani 1 1 d . . . H22A H 0.3075 0.2348 0.2520 0.053 Uiso 1 1 calc R . . C23 C 0.2551(2) 0.2353(3) 0.1074(4) 0.0402(11) Uani 1 1 d . . . H23A H 0.2951 0.2083 0.0663 0.048 Uiso 1 1 calc R . . C24 C 0.1892(2) 0.2595(3) 0.0574(3) 0.0347(10) Uani 1 1 d . . . H24A H 0.1844 0.2484 -0.0182 0.042 Uiso 1 1 calc R . . C25 C 0.0540(2) 0.4857(3) 0.0444(4) 0.0314(9) Uani 1 1 d . . . C26 C 0.0566(2) 0.5408(3) -0.0551(3) 0.0408(12) Uani 1 1 d . . . H26A H 0.0554 0.5004 -0.1204 0.049 Uiso 1 1 calc R . . C27 C 0.0607(3) 0.6524(4) -0.0597(4) 0.0507(14) Uani 1 1 d . . . H27A H 0.0626 0.6881 -0.1277 0.061 Uiso 1 1 calc R . . C28 C 0.0621(2) 0.7115(3) 0.0340(4) 0.0537(13) Uani 1 1 d . . . H28A H 0.0641 0.7883 0.0309 0.064 Uiso 1 1 calc R . . C29 C 0.0607(3) 0.6600(3) 0.1331(4) 0.0497(14) Uani 1 1 d . . . H29A H 0.0617 0.7014 0.1978 0.060 Uiso 1 1 calc R . . C30 C 0.0578(2) 0.5475(3) 0.1381(3) 0.0381(11) Uani 1 1 d . . . H30A H 0.0583 0.5125 0.2064 0.046 Uiso 1 1 calc R . . H1 H 0.099(2) 0.319(2) -0.151(3) 0.045(11) Uiso 1 1 d . . . H2 H 0.044(2) 0.195(3) -0.097(3) 0.051(12) Uiso 1 1 d . . . H3 H -0.009(2) 0.325(3) -0.130(3) 0.041(11) 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 0.0301(6) 0.0302(5) 0.0290(6) 0.0014(5) 0.0015(6) 0.0007(5) O1 0.0291(18) 0.0293(14) 0.0290(15) 0.0027(11) -0.0008(14) -0.0048(13) B1 0.043(4) 0.047(3) 0.035(3) -0.003(2) 0.004(3) 0.008(3) C1 0.021(2) 0.030(2) 0.027(2) -0.0019(17) -0.0007(19) -0.004(2) C2 0.025(2) 0.030(2) 0.024(2) 0.0007(16) 0.0019(18) -0.0003(19) C3 0.030(3) 0.025(2) 0.036(2) -0.0014(18) 0.005(2) 0.003(2) C4 0.025(3) 0.031(2) 0.033(2) -0.0049(19) 0.004(2) -0.004(2) C5 0.029(3) 0.034(2) 0.032(2) 0.0026(18) 0.002(2) 0.000(2) C6 0.027(2) 0.027(2) 0.029(2) 0.003(2) -0.005(2) 0.0009(18) C7 0.027(3) 0.030(2) 0.029(2) 0.0012(17) 0.000(2) 0.0031(19) C8 0.029(3) 0.033(2) 0.041(3) 0.0033(17) -0.001(2) 0.0044(19) C9 0.043(3) 0.033(2) 0.040(3) 0.0045(19) -0.003(2) 0.004(2) C10 0.047(3) 0.034(2) 0.047(3) 0.0125(19) 0.000(2) -0.001(2) C11 0.032(3) 0.029(2) 0.036(2) -0.0041(19) -0.005(2) 0.002(2) C12 0.076(5) 0.058(3) 0.065(3) 0.000(2) -0.040(3) -0.006(3) C13 0.054(4) 0.121(5) 0.079(4) -0.060(4) -0.017(3) 0.017(4) C14 0.070(4) 0.096(4) 0.070(4) 0.016(3) -0.021(3) -0.052(3) C15 0.027(3) 0.025(2) 0.040(3) -0.0026(17) -0.002(2) 0.0005(18) C16 0.040(3) 0.037(2) 0.052(3) -0.018(2) -0.004(2) 0.006(2) C17 0.053(4) 0.032(2) 0.058(3) 0.006(2) -0.002(3) 0.003(2) C18 0.040(3) 0.038(2) 0.062(3) -0.011(2) -0.001(2) 0.006(2) C19 0.030(3) 0.023(2) 0.035(3) 0.0000(18) -0.002(2) -0.0004(19) C20 0.043(3) 0.044(3) 0.030(3) -0.0057(19) -0.003(2) 0.009(2) C21 0.045(4) 0.051(3) 0.037(3) -0.004(2) -0.012(3) 0.011(3) C22 0.035(3) 0.034(2) 0.064(3) 0.005(2) -0.019(3) 0.001(2) C23 0.025(3) 0.041(3) 0.054(3) 0.004(2) 0.001(2) 0.002(2) C24 0.036(3) 0.031(2) 0.037(3) -0.0005(19) -0.002(3) -0.0011(19) C25 0.025(2) 0.0310(19) 0.038(2) 0.007(2) 0.002(2) 0.0008(18) C26 0.040(4) 0.041(3) 0.041(3) 0.002(2) 0.009(2) 0.002(2) C27 0.051(4) 0.037(3) 0.065(4) 0.016(2) 0.016(3) 0.005(2) C28 0.067(4) 0.025(2) 0.070(3) -0.002(3) 0.026(3) -0.002(2) C29 0.059(4) 0.035(3) 0.055(3) -0.006(2) 0.027(3) -0.005(2) C30 0.046(3) 0.034(2) 0.034(3) -0.004(2) 0.010(2) -0.005(2) _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 1.629(3) . ? P1 C19 1.804(4) . ? P1 C25 1.807(3) . ? P1 B1 1.917(5) . ? O1 C1 1.442(4) . ? B1 H3 1.10(4) . ? B1 H2 1.12(4) . ? B1 H1 1.27(4) . ? C1 C6 1.402(5) . ? C1 C2 1.406(5) . ? C2 C3 1.394(5) . ? C2 C7 1.550(5) . ? C3 C4 1.392(5) . ? C4 C5 1.389(5) . ? C4 C11 1.540(5) . ? C5 C6 1.397(5) . ? C6 C15 1.545(5) . ? C7 C8 1.527(5) . ? C7 C9 1.534(5) . ? C7 C10 1.551(5) . ? C11 C14 1.504(6) . ? C11 C12 1.515(5) . ? C11 C13 1.531(6) . ? C15 C16 1.523(5) . ? C15 C17 1.529(5) . ? C15 C18 1.538(6) . ? C19 C24 1.394(5) . ? C19 C20 1.401(5) . ? C20 C21 1.366(6) . ? C21 C22 1.392(6) . ? C22 C23 1.377(6) . ? C23 C24 1.385(5) . ? C25 C30 1.389(5) . ? C25 C26 1.407(5) . ? C26 C27 1.382(5) . ? C27 C28 1.370(6) . ? C28 C29 1.380(6) . ? C29 C30 1.393(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 C19 103.68(16) . . ? O1 P1 C25 106.81(16) . . ? C19 P1 C25 102.82(17) . . ? O1 P1 B1 115.2(2) . . ? C19 P1 B1 115.7(2) . . ? C25 P1 B1 111.5(2) . . ? C1 O1 P1 119.4(2) . . ? H3 B1 H2 120(3) . . ? H3 B1 H1 114(3) . . ? H2 B1 H1 109(2) . . ? H3 B1 P1 101.0(18) . . ? H2 B1 P1 106.6(19) . . ? H1 B1 P1 105.5(16) . . ? C6 C1 C2 122.8(3) . . ? C6 C1 O1 119.3(3) . . ? C2 C1 O1 117.8(3) . . ? C3 C2 C1 115.7(3) . . ? C3 C2 C7 117.8(3) . . ? C1 C2 C7 126.4(3) . . ? C4 C3 C2 123.5(3) . . ? C5 C4 C3 116.4(3) . . ? C5 C4 C11 122.0(4) . . ? C3 C4 C11 121.5(3) . . ? C4 C5 C6 123.8(4) . . ? C5 C6 C1 115.4(3) . . ? C5 C6 C15 117.1(3) . . ? C1 C6 C15 127.4(3) . . ? C8 C7 C9 110.3(3) . . ? C8 C7 C2 112.1(3) . . ? C9 C7 C2 111.6(3) . . ? C8 C7 C10 106.5(3) . . ? C9 C7 C10 106.0(3) . . ? C2 C7 C10 110.0(3) . . ? C14 C11 C12 109.1(4) . . ? C14 C11 C13 110.7(4) . . ? C12 C11 C13 106.0(4) . . ? C14 C11 C4 109.5(3) . . ? C12 C11 C4 112.5(3) . . ? C13 C11 C4 109.0(4) . . ? C16 C15 C17 110.4(3) . . ? C16 C15 C18 105.5(3) . . ? C17 C15 C18 107.1(3) . . ? C16 C15 C6 113.5(3) . . ? C17 C15 C6 110.0(3) . . ? C18 C15 C6 110.1(3) . . ? C24 C19 C20 117.8(4) . . ? C24 C19 P1 118.1(3) . . ? C20 C19 P1 124.0(3) . . ? C21 C20 C19 120.9(4) . . ? C20 C21 C22 120.3(4) . . ? C23 C22 C21 120.0(4) . . ? C22 C23 C24 119.5(4) . . ? C23 C24 C19 121.4(4) . . ? C30 C25 C26 117.5(3) . . ? C30 C25 P1 124.4(3) . . ? C26 C25 P1 118.1(3) . . ? C27 C26 C25 121.4(4) . . ? C28 C27 C26 119.8(4) . . ? C27 C28 C29 120.4(3) . . ? C28 C29 C30 120.0(4) . . ? C25 C30 C29 120.9(4) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.220 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.050 data_k00270 _database_code_CSD 181268 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H3 H15 B O3 P' _chemical_formula_weight 324.10 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' 'B' 'B' 0.0013 0.0007 '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' 'H' 'H' 0.0000 0.0000 '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 9.4189(3) _cell_length_b 9.9295(4) _cell_length_c 9.9979(3) _cell_angle_alpha 76.568(2) _cell_angle_beta 84.550(2) _cell_angle_gamma 72.735(2) _cell_volume 868.16(5) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 9.4189 _cell_measurement_theta_min 9.9295 _cell_measurement_theta_max 9.9979 _exptl_crystal_description 'plate' _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9670 _exptl_absorpt_correction_T_max 0.9833 _exptl_absorpt_process_details 'Denzo-SMN (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(1) _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 '\f scans and \w scans with \k offsets' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6801 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_av_sigmaI/netI 0.0641 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.69 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3054 _reflns_number_gt 2273 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2001)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_structure_refinement 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_molecular_graphics 'SHELXTL V5.1 (Sheldrick, 1999)' _computing_publication_material 'SHELXTL V5.1 (Sheldrick, 1999)' _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^)+(0.0358P)^2^+0.1689P] 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 0.017(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3054 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1041 _refine_ls_wR_factor_gt 0.0925 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _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 0.33174(7) 0.76424(6) 0.70472(5) 0.03423(19) Uani 1 1 d . . . O1 O 0.37771(16) 0.90937(14) 0.67870(13) 0.0358(4) Uani 1 1 d . . . O2 O 0.46759(16) 0.66981(15) 0.62974(13) 0.0400(4) Uani 1 1 d . . . O3 O 0.20145(16) 0.78968(15) 0.60557(13) 0.0357(4) Uani 1 1 d . . . C1 C 0.3225(2) 1.0181(2) 0.75529(18) 0.0304(5) Uani 1 1 d . . . C2 C 0.1725(2) 1.0800(2) 0.77092(19) 0.0333(5) Uani 1 1 d . . . H2A H 0.1023 1.0464 0.7357 0.040 Uiso 1 1 calc R . . C3 C 0.1262(3) 1.1926(2) 0.8392(2) 0.0404(5) Uani 1 1 d . . . H3A H 0.0228 1.2364 0.8516 0.048 Uiso 1 1 calc R . . C4 C 0.2283(3) 1.2419(2) 0.8894(2) 0.0471(6) Uani 1 1 d . . . H4A H 0.1955 1.3200 0.9352 0.056 Uiso 1 1 calc R . . C5 C 0.3777(3) 1.1774(3) 0.8729(2) 0.0505(6) Uani 1 1 d . . . H5A H 0.4482 1.2107 0.9080 0.061 Uiso 1 1 calc R . . C6 C 0.4263(3) 1.0641(2) 0.8054(2) 0.0422(6) Uani 1 1 d . . . H6A H 0.5295 1.0192 0.7940 0.051 Uiso 1 1 calc R . . C7 C 0.6194(2) 0.6480(2) 0.6514(2) 0.0341(5) Uani 1 1 d . . . C8 C 0.7085(3) 0.6766(2) 0.5373(2) 0.0434(6) Uani 1 1 d . . . H8A H 0.6667 0.7155 0.4489 0.052 Uiso 1 1 calc R . . C9 C 0.8596(3) 0.6481(2) 0.5530(2) 0.0490(6) Uani 1 1 d . . . H9A H 0.9222 0.6674 0.4750 0.059 Uiso 1 1 calc R . . C10 C 0.9197(3) 0.5916(2) 0.6818(2) 0.0472(6) Uani 1 1 d . . . H10A H 1.0234 0.5723 0.6927 0.057 Uiso 1 1 calc R . . C11 C 0.8286(3) 0.5634(2) 0.7941(2) 0.0440(6) Uani 1 1 d . . . H11A H 0.8703 0.5241 0.8825 0.053 Uiso 1 1 calc R . . C12 C 0.6777(3) 0.5912(2) 0.7806(2) 0.0382(5) Uani 1 1 d . . . H12A H 0.6153 0.5715 0.8586 0.046 Uiso 1 1 calc R . . C13 C 0.2092(2) 0.8382(2) 0.46034(19) 0.0311(5) Uani 1 1 d . . . C14 C 0.2483(2) 0.7366(2) 0.3805(2) 0.0368(5) Uani 1 1 d . . . H14A H 0.2756 0.6364 0.4215 0.044 Uiso 1 1 calc R . . C15 C 0.2470(2) 0.7839(2) 0.2389(2) 0.0391(5) Uani 1 1 d . . . H15A H 0.2745 0.7154 0.1819 0.047 Uiso 1 1 calc R . . C16 C 0.2062(2) 0.9292(2) 0.1799(2) 0.0377(5) Uani 1 1 d . . . H16A H 0.2048 0.9605 0.0826 0.045 Uiso 1 1 calc R . . C17 C 0.1671(2) 1.0293(2) 0.2624(2) 0.0381(5) Uani 1 1 d . . . H17A H 0.1391 1.1296 0.2215 0.046 Uiso 1 1 calc R . . C18 C 0.1687(2) 0.9842(2) 0.4043(2) 0.0337(5) Uani 1 1 d . . . H18A H 0.1425 1.0524 0.4616 0.040 Uiso 1 1 calc R . . B1 B 0.2802(4) 0.6855(3) 0.8858(3) 0.0467(7) Uani 1 1 d . . . H1 H 0.173(3) 0.755(3) 0.910(2) 0.054(7) Uiso 1 1 d . . . H2 H 0.369(3) 0.689(3) 0.948(2) 0.067(7) Uiso 1 1 d . . . H3 H 0.277(3) 0.575(3) 0.883(2) 0.073(8) 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 0.0438(4) 0.0321(3) 0.0258(3) -0.0079(2) 0.0014(2) -0.0088(3) O1 0.0400(9) 0.0338(8) 0.0341(7) -0.0117(6) 0.0079(6) -0.0108(7) O2 0.0444(10) 0.0395(9) 0.0340(8) -0.0161(6) -0.0001(7) -0.0029(7) O3 0.0413(9) 0.0414(8) 0.0254(7) -0.0080(6) 0.0028(6) -0.0136(7) C1 0.0376(13) 0.0282(11) 0.0247(10) -0.0063(8) 0.0004(9) -0.0081(9) C2 0.0335(12) 0.0349(12) 0.0323(11) -0.0089(9) -0.0044(9) -0.0086(10) C3 0.0375(13) 0.0389(13) 0.0409(12) -0.0126(10) -0.0006(10) -0.0021(10) C4 0.0587(17) 0.0400(13) 0.0475(13) -0.0191(10) -0.0005(12) -0.0144(12) C5 0.0536(17) 0.0550(15) 0.0555(15) -0.0226(12) -0.0053(12) -0.0252(13) C6 0.0342(13) 0.0498(14) 0.0459(13) -0.0150(11) -0.0018(10) -0.0130(11) C7 0.0405(13) 0.0246(11) 0.0323(11) -0.0076(8) 0.0004(10) -0.0010(9) C8 0.0588(17) 0.0311(12) 0.0312(11) -0.0016(9) 0.0022(11) -0.0040(11) C9 0.0550(17) 0.0360(13) 0.0486(14) -0.0045(10) 0.0145(12) -0.0101(11) C10 0.0454(15) 0.0360(13) 0.0582(15) -0.0126(11) 0.0008(12) -0.0074(11) C11 0.0497(16) 0.0384(13) 0.0381(12) -0.0112(10) -0.0033(11) -0.0012(11) C12 0.0468(14) 0.0333(12) 0.0296(11) -0.0084(9) 0.0054(10) -0.0046(10) C13 0.0310(12) 0.0376(12) 0.0264(10) -0.0074(8) 0.0009(9) -0.0124(9) C14 0.0448(14) 0.0327(12) 0.0343(11) -0.0088(9) 0.0007(10) -0.0122(10) C15 0.0445(14) 0.0460(14) 0.0328(11) -0.0157(10) 0.0046(10) -0.0178(11) C16 0.0406(13) 0.0477(14) 0.0264(10) -0.0040(9) -0.0011(9) -0.0179(11) C17 0.0382(13) 0.0343(12) 0.0398(12) -0.0021(9) -0.0031(10) -0.0114(10) C18 0.0321(12) 0.0351(12) 0.0357(11) -0.0119(9) 0.0008(9) -0.0096(9) B1 0.064(2) 0.0454(17) 0.0284(13) -0.0066(11) 0.0024(13) -0.0143(15) _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 O3 1.5757(14) . ? P1 O1 1.5832(15) . ? P1 O2 1.5845(15) . ? P1 B1 1.878(3) . ? O1 C1 1.413(2) . ? O2 C7 1.411(3) . ? O3 C13 1.422(2) . ? C1 C6 1.371(3) . ? C1 C2 1.373(3) . ? C2 C3 1.383(3) . ? C3 C4 1.380(3) . ? C4 C5 1.374(3) . ? C5 C6 1.384(3) . ? C7 C8 1.376(3) . ? C7 C12 1.379(3) . ? C8 C9 1.383(3) . ? C9 C10 1.381(3) . ? C10 C11 1.374(3) . ? C11 C12 1.379(3) . ? C13 C14 1.375(3) . ? C13 C18 1.377(3) . ? C14 C15 1.384(3) . ? C15 C16 1.376(3) . ? C16 C17 1.382(3) . ? C17 C18 1.385(3) . ? B1 H1 1.08(2) . ? B1 H2 1.10(2) . ? B1 H3 1.11(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 O3 P1 O1 107.72(8) . . ? O3 P1 O2 101.27(7) . . ? O1 P1 O2 99.92(8) . . ? O3 P1 B1 110.32(12) . . ? O1 P1 B1 117.56(11) . . ? O2 P1 B1 118.32(11) . . ? C1 O1 P1 124.99(13) . . ? C7 O2 P1 125.72(12) . . ? C13 O3 P1 124.47(13) . . ? C6 C1 C2 122.06(19) . . ? C6 C1 O1 116.50(18) . . ? C2 C1 O1 121.32(17) . . ? C1 C2 C3 118.35(19) . . ? C4 C3 C2 120.7(2) . . ? C5 C4 C3 119.6(2) . . ? C4 C5 C6 120.5(2) . . ? C1 C6 C5 118.7(2) . . ? C8 C7 C12 121.4(2) . . ? C8 C7 O2 117.32(18) . . ? C12 C7 O2 121.12(19) . . ? C7 C8 C9 119.2(2) . . ? C10 C9 C8 120.1(2) . . ? C11 C10 C9 119.6(2) . . ? C10 C11 C12 121.1(2) . . ? C11 C12 C7 118.5(2) . . ? C14 C13 C18 122.30(18) . . ? C14 C13 O3 118.24(17) . . ? C18 C13 O3 119.34(17) . . ? C13 C14 C15 118.29(19) . . ? C16 C15 C14 120.72(19) . . ? C15 C16 C17 119.91(19) . . ? C16 C17 C18 120.28(19) . . ? C13 C18 C17 118.50(19) . . ? H1 B1 H2 112.4(17) . . ? H1 B1 H3 113.0(19) . . ? H2 B1 H3 114.5(17) . . ? H1 B1 P1 106.8(12) . . ? H2 B1 P1 104.5(13) . . ? H3 B1 P1 104.6(13) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.174 _refine_diff_density_min -0.286 _refine_diff_density_rms 0.041