# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 #TrackingRef '- Compound 10.CIF' _publ_contact_author_name 'David J. Cole-Hamilton' _publ_contact_author_address ; EaStCHEM, School of Chemistry, Purdie Building, University of St. Andrews, St. Andrews, Fife, KY16 9QS, Scotland, UK ; _publ_contact_author_email djc@st-andrews.ac.uk _publ_contact_author_fax '+44 1334 463808' _publ_contact_author_phone '+44 1334 463805' loop_ _publ_author_name _publ_author_address 'Jacorien Coetzee' ; EaStCHEM, School of Chemistry, Purdie Building, University of St. Andrews, St. Andrews, Fife, KY16 9QS, Scotland, UK ; 'Graham R. Eastham' ; Lucite International Technology Centre, P.O. Box 90, Wilton, Middlesborough, Cleveland, TS6 8JE, England, UK ; 'Alexandra M. Z. Slawin' ; EaStCHEM, School of Chemistry, Purdie Building, University of St. Andrews, St. Andrews, Fife, KY16 9QS, Scotland, UK ; D.Cole-Hamilton '' data_compound10 _database_code_depnum_ccdc_archive 'CCDC 860547' #TrackingRef '- Compound 10.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4,8-di-tert-butyl-1,2,10,11-tetramethyldibenzo [d,f][1,3,2]dioxaphosphepin-6-yl propionate' ; _chemical_name_common ;Propionyl-(5,5'6,6'-Tetramethyl-3,3' -di-tert-butyl-1,1-biphenyl)phosphite' ; _chemical_melting_point 150-153 _chemical_formula_moiety 'C27 H37 O4 P' _chemical_formula_sum 'C27 H37 O4 P' _chemical_formula_weight 456.54 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 Orthorhombic _symmetry_space_group_name_H-M Pna21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 15.562(6) _cell_length_b 10.686(4) _cell_length_c 15.625(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2598.3(17) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 6096 _cell_measurement_theta_min 1.9058 _cell_measurement_theta_max 28.3203 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9633 _exptl_absorpt_correction_T_max 0.9920 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15727 _diffrn_reflns_av_R_equivalents 0.1675 _diffrn_reflns_av_sigmaI/netI 0.1350 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.31 _diffrn_reflns_theta_max 25.32 _reflns_number_total 4127 _reflns_number_gt 2501 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.1260P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(3) _refine_ls_number_reflns 4127 _refine_ls_number_parameters 301 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1454 _refine_ls_R_factor_gt 0.0919 _refine_ls_wR_factor_ref 0.2483 _refine_ls_wR_factor_gt 0.2162 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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 0.21116(13) 0.22406(16) 0.29030(13) 0.0457(5) Uani 1 1 d . . . O4 O 0.2163(3) 0.1805(4) 0.3911(3) 0.0404(11) Uani 1 1 d . . . O1 O 0.1051(3) 0.2327(4) 0.2929(4) 0.0557(13) Uani 1 1 d . . . O2 O 0.0981(5) 0.0323(7) 0.2709(7) 0.130(3) Uani 1 1 d . . . O3 O 0.2341(3) 0.3713(4) 0.2936(3) 0.0473(12) Uani 1 1 d . . . C10 C 0.2977(4) 0.1987(6) 0.4300(4) 0.0375(16) Uani 1 1 d . . . C11 C 0.3534(4) 0.0994(6) 0.4442(4) 0.0409(16) Uani 1 1 d . . . C12 C 0.4321(5) 0.1334(6) 0.4781(4) 0.0470(18) Uani 1 1 d . . . H12 H 0.4723 0.0685 0.4889 0.056 Uiso 1 1 calc R . . C13 C 0.4571(5) 0.2562(7) 0.4977(5) 0.0448(18) Uani 1 1 d . . . C14 C 0.3985(4) 0.3527(6) 0.4847(4) 0.0401(16) Uani 1 1 d . . . C15 C 0.3157(5) 0.3227(6) 0.4524(4) 0.0391(15) Uani 1 1 d . . . C9 C 0.2471(4) 0.4217(6) 0.4437(4) 0.0377(16) Uani 1 1 d . . . C4 C 0.2114(5) 0.4495(6) 0.3631(4) 0.0437(18) Uani 1 1 d . . . C5 C 0.1589(4) 0.5564(6) 0.3473(5) 0.0433(18) Uani 1 1 d . . . C6 C 0.1362(5) 0.6215(6) 0.4222(5) 0.0466(18) Uani 1 1 d . . . H6 H 0.1011 0.6938 0.4163 0.056 Uiso 1 1 calc R . . C7 C 0.1610(4) 0.5882(6) 0.5022(4) 0.0411(17) Uani 1 1 d . . . C8 C 0.2175(4) 0.4893(6) 0.5165(4) 0.0372(16) Uani 1 1 d . . . C17 C 0.3266(5) -0.0385(6) 0.4300(5) 0.0480(18) Uani 1 1 d . . . C21 C 0.2427(5) -0.0666(7) 0.4784(6) 0.058(2) Uani 1 1 d . . . H21A H 0.2523 -0.0570 0.5400 0.087 Uiso 1 1 calc R . . H21B H 0.2244 -0.1526 0.4662 0.087 Uiso 1 1 calc R . . H21C H 0.1978 -0.0082 0.4598 0.087 Uiso 1 1 calc R . . C22 C 0.3159(5) -0.0664(7) 0.3357(5) 0.056(2) Uani 1 1 d . . . H22A H 0.2645 -0.0238 0.3141 0.084 Uiso 1 1 calc R . . H22B H 0.3097 -0.1569 0.3274 0.084 Uiso 1 1 calc R . . H22C H 0.3665 -0.0366 0.3044 0.084 Uiso 1 1 calc R . . C23 C 0.3968(5) -0.1273(6) 0.4660(6) 0.064(2) Uani 1 1 d . . . H23A H 0.4522 -0.1075 0.4395 0.096 Uiso 1 1 calc R . . H23B H 0.3814 -0.2143 0.4532 0.096 Uiso 1 1 calc R . . H23C H 0.4010 -0.1163 0.5281 0.096 Uiso 1 1 calc R . . C25 C 0.5482(5) 0.2809(7) 0.5301(5) 0.052(2) Uani 1 1 d . . . H25A H 0.5760 0.3433 0.4934 0.078 Uiso 1 1 calc R . . H25B H 0.5813 0.2029 0.5287 0.078 Uiso 1 1 calc R . . H25C H 0.5457 0.3123 0.5890 0.078 Uiso 1 1 calc R . . C27 C 0.4248(5) 0.4841(7) 0.5038(5) 0.058(2) Uani 1 1 d . . . H27A H 0.4264 0.4966 0.5659 0.088 Uiso 1 1 calc R . . H27B H 0.3834 0.5422 0.4782 0.088 Uiso 1 1 calc R . . H27C H 0.4820 0.4998 0.4798 0.088 Uiso 1 1 calc R . . C16 C 0.1301(5) 0.5999(6) 0.2577(5) 0.053(2) Uani 1 1 d . . . C18 C 0.0847(6) 0.7266(7) 0.2624(5) 0.065(3) Uani 1 1 d . . . H18A H 0.1220 0.7872 0.2914 0.098 Uiso 1 1 calc R . . H18B H 0.0309 0.7178 0.2943 0.098 Uiso 1 1 calc R . . H18C H 0.0722 0.7562 0.2043 0.098 Uiso 1 1 calc R . . C19 C 0.0680(5) 0.5045(7) 0.2168(5) 0.060(2) Uani 1 1 d . . . H19A H 0.0225 0.4833 0.2577 0.090 Uiso 1 1 calc R . . H19B H 0.0997 0.4286 0.2013 0.090 Uiso 1 1 calc R . . H19C H 0.0422 0.5411 0.1653 0.090 Uiso 1 1 calc R . . C20 C 0.2099(6) 0.6165(7) 0.2013(5) 0.059(2) Uani 1 1 d . . . H20A H 0.1925 0.6465 0.1446 0.089 Uiso 1 1 calc R . . H20B H 0.2395 0.5361 0.1955 0.089 Uiso 1 1 calc R . . H20C H 0.2486 0.6776 0.2277 0.089 Uiso 1 1 calc R . . C24 C 0.1253(5) 0.6604(6) 0.5799(5) 0.0448(17) Uani 1 1 d . . . H24A H 0.0863 0.7263 0.5600 0.067 Uiso 1 1 calc R . . H24B H 0.1730 0.6982 0.6117 0.067 Uiso 1 1 calc R . . H24C H 0.0940 0.6026 0.6173 0.067 Uiso 1 1 calc R . . C26 C 0.2426(5) 0.4525(7) 0.6052(4) 0.0483(19) Uani 1 1 d . . . H26A H 0.2791 0.3779 0.6030 0.072 Uiso 1 1 calc R . . H26B H 0.1908 0.4343 0.6387 0.072 Uiso 1 1 calc R . . H26C H 0.2743 0.5213 0.6322 0.072 Uiso 1 1 calc R . . C1 C 0.0589(6) 0.1436(11) 0.2623(9) 0.119(5) Uani 1 1 d . . . C2 C -0.0339(5) 0.1547(7) 0.2575(5) 0.0522(19) Uani 1 1 d . . . H2A H -0.0500 0.2090 0.2088 0.063 Uiso 1 1 calc R . . H2B H -0.0562 0.1931 0.3107 0.063 Uiso 1 1 calc R . . C3 C -0.0717(9) 0.0292(13) 0.2461(12) 0.205(11) Uani 1 1 d . . . H3A H -0.0603 -0.0003 0.1878 0.307 Uiso 1 1 calc R . . H3B H -0.1339 0.0334 0.2556 0.307 Uiso 1 1 calc R . . H3C H -0.0459 -0.0289 0.2873 0.307 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 0.0665(13) 0.0331(9) 0.0374(10) -0.0035(9) -0.0009(11) -0.0020(8) O4 0.050(3) 0.032(2) 0.039(3) -0.007(2) -0.001(2) -0.001(2) O1 0.063(3) 0.049(3) 0.055(3) -0.014(3) -0.009(3) 0.012(2) O2 0.104(6) 0.079(5) 0.208(10) -0.038(6) 0.013(6) 0.006(4) O3 0.070(3) 0.037(2) 0.034(2) -0.002(2) 0.005(3) -0.002(2) C10 0.044(4) 0.039(4) 0.030(4) 0.001(3) 0.003(3) -0.005(3) C11 0.047(4) 0.040(4) 0.036(4) -0.003(3) -0.003(3) 0.012(3) C12 0.065(5) 0.036(4) 0.040(4) -0.006(3) -0.006(4) 0.014(3) C13 0.051(5) 0.042(4) 0.041(4) 0.000(3) 0.007(3) -0.013(4) C14 0.049(4) 0.033(3) 0.038(4) -0.003(3) 0.002(3) -0.003(3) C15 0.056(4) 0.031(3) 0.031(3) 0.002(3) 0.000(3) -0.001(3) C9 0.045(4) 0.036(4) 0.031(4) 0.001(3) -0.007(3) -0.009(3) C4 0.056(5) 0.035(4) 0.040(5) -0.001(3) 0.008(4) -0.007(3) C5 0.047(4) 0.039(4) 0.044(4) -0.010(3) -0.003(4) -0.002(3) C6 0.056(5) 0.029(3) 0.055(5) -0.011(3) 0.002(4) -0.002(3) C7 0.041(4) 0.035(4) 0.046(4) -0.007(3) 0.000(3) -0.009(3) C8 0.045(4) 0.036(4) 0.031(3) 0.000(3) 0.001(3) -0.002(3) C17 0.061(5) 0.028(3) 0.054(5) -0.008(3) -0.006(4) 0.005(3) C21 0.071(6) 0.039(4) 0.063(5) -0.010(4) -0.001(4) -0.003(4) C22 0.064(5) 0.048(5) 0.056(5) -0.008(4) -0.009(4) 0.007(4) C23 0.078(6) 0.034(4) 0.080(6) -0.010(4) -0.016(5) 0.001(4) C25 0.042(5) 0.053(5) 0.061(5) 0.003(4) -0.021(4) -0.005(3) C27 0.063(5) 0.039(4) 0.073(6) -0.009(4) -0.012(4) -0.005(4) C16 0.089(6) 0.030(4) 0.039(4) 0.009(3) -0.016(4) -0.001(4) C18 0.103(7) 0.039(4) 0.054(5) 0.009(4) -0.018(5) 0.013(4) C19 0.081(6) 0.049(4) 0.051(5) 0.011(4) -0.019(5) -0.008(4) C20 0.093(6) 0.049(4) 0.037(4) 0.015(3) -0.001(4) -0.004(4) C24 0.049(4) 0.030(3) 0.055(5) 0.002(3) 0.001(4) 0.008(3) C26 0.069(5) 0.037(4) 0.039(4) -0.011(3) 0.010(4) 0.000(4) C1 0.064(7) 0.101(8) 0.193(14) -0.104(9) 0.027(7) -0.026(6) C2 0.060(5) 0.049(4) 0.048(4) -0.004(3) -0.004(4) 0.003(4) C3 0.133(11) 0.125(11) 0.36(3) -0.154(15) 0.134(15) -0.073(9) _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 1.614(5) . ? P1 O4 1.645(5) . ? P1 O1 1.654(5) . ? O4 C10 1.418(8) . ? O1 C1 1.284(10) . ? O2 C1 1.343(14) . ? O3 C4 1.415(8) . ? C10 C11 1.389(9) . ? C10 C15 1.398(9) . ? C11 C12 1.382(10) . ? C11 C17 1.547(9) . ? C12 C13 1.403(10) . ? C12 H12 0.9500 . ? C13 C14 1.393(10) . ? C13 C25 1.527(10) . ? C14 C15 1.420(10) . ? C14 C27 1.493(9) . ? C15 C9 1.509(9) . ? C9 C4 1.408(9) . ? C9 C8 1.424(9) . ? C4 C5 1.427(10) . ? C5 C6 1.407(9) . ? C5 C16 1.541(10) . ? C6 C7 1.356(9) . ? C6 H6 0.9500 . ? C7 C8 1.392(10) . ? C7 C24 1.542(10) . ? C8 C26 1.493(10) . ? C17 C22 1.513(10) . ? C17 C21 1.539(11) . ? C17 C23 1.553(10) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C16 C18 1.528(10) . ? C16 C20 1.534(11) . ? C16 C19 1.544(10) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C1 C2 1.452(12) . ? C2 C3 1.475(12) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 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 O3 P1 O4 103.6(2) . . ? O3 P1 O1 99.5(3) . . ? O4 P1 O1 92.3(3) . . ? C10 O4 P1 114.5(4) . . ? C1 O1 P1 120.5(6) . . ? C4 O3 P1 123.0(4) . . ? C11 C10 C15 124.0(6) . . ? C11 C10 O4 121.4(6) . . ? C15 C10 O4 114.6(6) . . ? C12 C11 C10 114.4(6) . . ? C12 C11 C17 123.0(6) . . ? C10 C11 C17 122.4(6) . . ? C11 C12 C13 125.2(6) . . ? C11 C12 H12 117.4 . . ? C13 C12 H12 117.4 . . ? C14 C13 C12 118.6(6) . . ? C14 C13 C25 121.9(6) . . ? C12 C13 C25 119.5(6) . . ? C13 C14 C15 118.6(6) . . ? C13 C14 C27 119.2(7) . . ? C15 C14 C27 122.2(6) . . ? C10 C15 C14 119.0(6) . . ? C10 C15 C9 120.0(6) . . ? C14 C15 C9 121.0(6) . . ? C4 C9 C8 118.6(6) . . ? C4 C9 C15 120.5(6) . . ? C8 C9 C15 120.9(6) . . ? C9 C4 O3 117.6(6) . . ? C9 C4 C5 123.4(6) . . ? O3 C4 C5 118.9(6) . . ? C6 C5 C4 113.3(7) . . ? C6 C5 C16 122.2(6) . . ? C4 C5 C16 124.5(6) . . ? C7 C6 C5 124.4(6) . . ? C7 C6 H6 117.8 . . ? C5 C6 H6 117.8 . . ? C6 C7 C8 121.8(6) . . ? C6 C7 C24 119.5(6) . . ? C8 C7 C24 118.7(6) . . ? C7 C8 C9 117.5(6) . . ? C7 C8 C26 120.9(6) . . ? C9 C8 C26 121.5(6) . . ? C22 C17 C21 110.3(7) . . ? C22 C17 C11 110.9(6) . . ? C21 C17 C11 110.2(5) . . ? C22 C17 C23 108.1(6) . . ? C21 C17 C23 107.4(7) . . ? C11 C17 C23 109.9(6) . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C17 C23 H23A 109.5 . . ? C17 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C17 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C13 C25 H25A 109.5 . . ? C13 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C13 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C14 C27 H27A 109.5 . . ? C14 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C14 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C18 C16 C20 107.4(6) . . ? C18 C16 C5 111.0(6) . . ? C20 C16 C5 108.7(6) . . ? C18 C16 C19 108.4(7) . . ? C20 C16 C19 110.2(7) . . ? C5 C16 C19 111.1(6) . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C16 C19 H19A 109.5 . . ? C16 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C16 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C16 C20 H20A 109.5 . . ? C16 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C16 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C7 C24 H24A 109.5 . . ? C7 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C7 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C8 C26 H26A 109.5 . . ? C8 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C8 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? O1 C1 O2 111.4(10) . . ? O1 C1 C2 121.0(8) . . ? O2 C1 C2 122.0(8) . . ? C1 C2 C3 109.2(9) . . ? C1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? C1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.3 . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 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 O3 P1 O4 C10 -60.0(4) . . . . ? O1 P1 O4 C10 -160.4(4) . . . . ? O3 P1 O1 C1 155.7(10) . . . . ? O4 P1 O1 C1 -100.2(10) . . . . ? O4 P1 O3 C4 -33.0(6) . . . . ? O1 P1 O3 C4 61.8(6) . . . . ? P1 O4 C10 C11 -103.6(6) . . . . ? P1 O4 C10 C15 76.6(6) . . . . ? C15 C10 C11 C12 -3.8(10) . . . . ? O4 C10 C11 C12 176.5(6) . . . . ? C15 C10 C11 C17 171.5(7) . . . . ? O4 C10 C11 C17 -8.3(10) . . . . ? C10 C11 C12 C13 -0.1(10) . . . . ? C17 C11 C12 C13 -175.3(6) . . . . ? C11 C12 C13 C14 1.8(11) . . . . ? C11 C12 C13 C25 -176.5(7) . . . . ? C12 C13 C14 C15 0.2(10) . . . . ? C25 C13 C14 C15 178.4(7) . . . . ? C12 C13 C14 C27 -178.9(7) . . . . ? C25 C13 C14 C27 -0.7(10) . . . . ? C11 C10 C15 C14 5.8(10) . . . . ? O4 C10 C15 C14 -174.4(6) . . . . ? C11 C10 C15 C9 -173.0(6) . . . . ? O4 C10 C15 C9 6.7(9) . . . . ? C13 C14 C15 C10 -3.7(10) . . . . ? C27 C14 C15 C10 175.3(7) . . . . ? C13 C14 C15 C9 175.1(6) . . . . ? C27 C14 C15 C9 -5.9(10) . . . . ? C10 C15 C9 C4 -61.4(9) . . . . ? C14 C15 C9 C4 119.8(7) . . . . ? C10 C15 C9 C8 118.8(7) . . . . ? C14 C15 C9 C8 -60.0(9) . . . . ? C8 C9 C4 O3 -172.5(5) . . . . ? C15 C9 C4 O3 7.7(9) . . . . ? C8 C9 C4 C5 11.9(10) . . . . ? C15 C9 C4 C5 -167.9(6) . . . . ? P1 O3 C4 C9 62.6(7) . . . . ? P1 O3 C4 C5 -121.6(6) . . . . ? C9 C4 C5 C6 -8.5(9) . . . . ? O3 C4 C5 C6 176.0(6) . . . . ? C9 C4 C5 C16 170.5(6) . . . . ? O3 C4 C5 C16 -5.0(10) . . . . ? C4 C5 C6 C7 0.1(10) . . . . ? C16 C5 C6 C7 -178.9(7) . . . . ? C5 C6 C7 C8 4.8(11) . . . . ? C5 C6 C7 C24 -174.6(6) . . . . ? C6 C7 C8 C9 -1.4(10) . . . . ? C24 C7 C8 C9 178.0(6) . . . . ? C6 C7 C8 C26 -178.8(7) . . . . ? C24 C7 C8 C26 0.7(10) . . . . ? C4 C9 C8 C7 -6.5(9) . . . . ? C15 C9 C8 C7 173.3(6) . . . . ? C4 C9 C8 C26 170.8(6) . . . . ? C15 C9 C8 C26 -9.4(9) . . . . ? C12 C11 C17 C22 -114.7(8) . . . . ? C10 C11 C17 C22 70.4(8) . . . . ? C12 C11 C17 C21 122.8(8) . . . . ? C10 C11 C17 C21 -52.1(9) . . . . ? C12 C11 C17 C23 4.7(9) . . . . ? C10 C11 C17 C23 -170.2(7) . . . . ? C6 C5 C16 C18 6.6(10) . . . . ? C4 C5 C16 C18 -172.4(7) . . . . ? C6 C5 C16 C20 124.5(7) . . . . ? C4 C5 C16 C20 -54.5(9) . . . . ? C6 C5 C16 C19 -114.1(8) . . . . ? C4 C5 C16 C19 66.9(9) . . . . ? P1 O1 C1 O2 31.2(15) . . . . ? P1 O1 C1 C2 -174.7(9) . . . . ? O1 C1 C2 C3 -162.6(13) . . . . ? O2 C1 C2 C3 -11.2(18) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.32 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.957 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.073 # Attachment '- Compound 11.CIF' data_compound11 _database_code_depnum_ccdc_archive 'CCDC 860548' #TrackingRef '- Compound 11.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '4,8-di-tert-butyl-1,2,10,11-tetramethyldibenzo [d,f][1,3,2]dioxaphosphepin-6-yl 2-phenylacetate' ; _chemical_name_common ; phenylacetyl-(5,5',6,6'-tetramethyl-3,3'-di-tert-butyl- 1,1'-biphenyl-2,2'-diyl)phosphite' ; _chemical_melting_point '164-166 deg C' _chemical_formula_moiety 'C32 H39 O4 P' _chemical_formula_sum 'C32 H39 O4 P' _chemical_formula_weight 518.60 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 P21/n _symmetry_space_group_name_Hall -P2yn 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 10.820(7) _cell_length_b 16.178(10) _cell_length_c 15.982(10) _cell_angle_alpha 90.00 _cell_angle_beta 98.366(17) _cell_angle_gamma 90.00 _cell_volume 2768(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 9258 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 28.9 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.135 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18083 _diffrn_reflns_av_R_equivalents 0.2879 _diffrn_reflns_av_sigmaI/netI 0.3208 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.46 _reflns_number_total 5075 _reflns_number_gt 2310 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.1809P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_number_reflns 5075 _refine_ls_number_parameters 344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2445 _refine_ls_R_factor_gt 0.1477 _refine_ls_wR_factor_ref 0.3668 _refine_ls_wR_factor_gt 0.3207 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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 0.99349(16) 0.20536(10) 0.90511(10) 0.0304(5) Uani 1 1 d . . . O3 O 1.0584(4) 0.2094(2) 1.0036(2) 0.0277(11) Uani 1 1 d . . . O1 O 0.9830(4) 0.1017(2) 0.9061(3) 0.0324(12) Uani 1 1 d . . . O4 O 0.8503(4) 0.2271(2) 0.9115(2) 0.0293(11) Uani 1 1 d . . . O2 O 1.1796(5) 0.0932(3) 0.8808(4) 0.0562(16) Uani 1 1 d . . . C18 C 0.6881(6) 0.1743(4) 1.1264(4) 0.0295(16) Uani 1 1 d . . . C15 C 0.7915(6) 0.2085(4) 0.9821(4) 0.0279(16) Uani 1 1 d . . . C16 C 0.6928(6) 0.1507(3) 0.9748(4) 0.0264(15) Uani 1 1 d . . . C14 C 0.9379(6) 0.3137(3) 1.0599(4) 0.0256(15) Uani 1 1 d . . . C11 C 1.1440(7) 0.4182(4) 1.0859(4) 0.0343(18) Uani 1 1 d . . . H11 H 1.2140 0.4539 1.0979 0.041 Uiso 1 1 calc R . . C3 C 1.0033(6) -0.0581(4) 0.7971(4) 0.0338(17) Uani 1 1 d . . . C30 C 0.6751(7) 0.1291(4) 0.8107(4) 0.0419(19) Uani 1 1 d . . . H30A H 0.6319 0.0951 0.7647 0.063 Uiso 1 1 calc R . . H30B H 0.7656 0.1239 0.8119 0.063 Uiso 1 1 calc R . . H30C H 0.6505 0.1870 0.8014 0.063 Uiso 1 1 calc R . . C12 C 1.0279(6) 0.4468(4) 1.0982(3) 0.0286(16) Uani 1 1 d . . . C25 C 1.0182(7) 0.5357(4) 1.1300(4) 0.0363(17) Uani 1 1 d . . . H25A H 0.9536 0.5654 1.0924 0.054 Uiso 1 1 calc R . . H25B H 1.0987 0.5637 1.1307 0.054 Uiso 1 1 calc R . . H25C H 0.9962 0.5348 1.1874 0.054 Uiso 1 1 calc R . . C10 C 1.1623(6) 0.3380(4) 1.0562(4) 0.0293(16) Uani 1 1 d . . . C17 C 0.6450(6) 0.1382(4) 1.0490(4) 0.0305(16) Uani 1 1 d . . . H17 H 0.5762 0.1014 1.0470 0.037 Uiso 1 1 calc R . . C19 C 0.7858(6) 0.2318(3) 1.1314(4) 0.0292(16) Uani 1 1 d . . . C4 C 1.0548(7) -0.0358(4) 0.7246(4) 0.0423(18) Uani 1 1 d . . . H4 H 1.1279 -0.0026 0.7305 0.051 Uiso 1 1 calc R . . C8 C 0.8979(6) -0.1094(4) 0.7846(5) 0.0383(18) Uani 1 1 d . . . H8 H 0.8619 -0.1277 0.8321 0.046 Uiso 1 1 calc R . . C2 C 1.0618(7) -0.0333(4) 0.8847(4) 0.0393(18) Uani 1 1 d . . . H2A H 1.1424 -0.0625 0.8996 0.047 Uiso 1 1 calc R . . H2B H 1.0064 -0.0498 0.9259 0.047 Uiso 1 1 calc R . . C20 C 0.8356(6) 0.2498(3) 1.0579(4) 0.0267(15) Uani 1 1 d . . . C13 C 0.9242(6) 0.3963(3) 1.0870(4) 0.0255(15) Uani 1 1 d . . . C32 C 0.4969(6) 0.0999(4) 0.8853(4) 0.0415(19) Uani 1 1 d . . . H32A H 0.4664 0.1570 0.8815 0.062 Uiso 1 1 calc R . . H32B H 0.4699 0.0728 0.9344 0.062 Uiso 1 1 calc R . . H32C H 0.4630 0.0699 0.8337 0.062 Uiso 1 1 calc R . . C1 C 1.0838(7) 0.0592(4) 0.8901(4) 0.0358(18) Uani 1 1 d . . . C29 C 0.6398(6) 0.0997(4) 0.8949(4) 0.0301(16) Uani 1 1 d . . . C28 C 0.6323(6) 0.1526(4) 1.2046(4) 0.0364(17) Uani 1 1 d . . . H28A H 0.5647 0.1124 1.1902 0.055 Uiso 1 1 calc R . . H28B H 0.5989 0.2026 1.2277 0.055 Uiso 1 1 calc R . . H28C H 0.6969 0.1286 1.2470 0.055 Uiso 1 1 calc R . . C9 C 1.0538(6) 0.2903(3) 1.0405(4) 0.0276(16) Uani 1 1 d . . . C7 C 0.8462(8) -0.1335(4) 0.7055(6) 0.053(2) Uani 1 1 d . . . H7 H 0.7730 -0.1667 0.6988 0.063 Uiso 1 1 calc R . . C26 C 0.7983(6) 0.4287(4) 1.1007(4) 0.0398(18) Uani 1 1 d . . . H26A H 0.7991 0.4410 1.1608 0.060 Uiso 1 1 calc R . . H26B H 0.7343 0.3869 1.0827 0.060 Uiso 1 1 calc R . . H26C H 0.7794 0.4792 1.0674 0.060 Uiso 1 1 calc R . . C27 C 0.8403(6) 0.2664(4) 1.2179(4) 0.0369(17) Uani 1 1 d . . . H27A H 0.9148 0.2992 1.2125 0.055 Uiso 1 1 calc R . . H27B H 0.8629 0.2207 1.2574 0.055 Uiso 1 1 calc R . . H27C H 0.7780 0.3015 1.2393 0.055 Uiso 1 1 calc R . . C21 C 1.2909(6) 0.3072(4) 1.0420(4) 0.0321(16) Uani 1 1 d . . . C24 C 1.3235(7) 0.2239(4) 1.0881(5) 0.046(2) Uani 1 1 d . . . H24A H 1.3158 0.2299 1.1482 0.070 Uiso 1 1 calc R . . H24B H 1.4093 0.2082 1.0824 0.070 Uiso 1 1 calc R . . H24C H 1.2658 0.1810 1.0629 0.070 Uiso 1 1 calc R . . C22 C 1.3928(7) 0.3675(4) 1.0773(4) 0.0406(18) Uani 1 1 d . . . H22A H 1.3779 0.4210 1.0489 0.061 Uiso 1 1 calc R . . H22B H 1.4742 0.3459 1.0677 0.061 Uiso 1 1 calc R . . H22C H 1.3922 0.3745 1.1381 0.061 Uiso 1 1 calc R . . C31 C 0.6872(7) 0.0099(4) 0.9115(4) 0.0428(19) Uani 1 1 d . . . H31A H 0.6576 -0.0245 0.8622 0.064 Uiso 1 1 calc R . . H31B H 0.6552 -0.0122 0.9613 0.064 Uiso 1 1 calc R . . H31C H 0.7787 0.0096 0.9215 0.064 Uiso 1 1 calc R . . C5 C 1.0021(9) -0.0608(5) 0.6461(5) 0.055(2) Uani 1 1 d . . . H5 H 1.0378 -0.0435 0.5981 0.066 Uiso 1 1 calc R . . C23 C 1.2951(7) 0.2963(4) 0.9478(4) 0.0408(18) Uani 1 1 d . . . H23A H 1.2377 0.2521 0.9256 0.061 Uiso 1 1 calc R . . H23B H 1.3802 0.2818 0.9390 0.061 Uiso 1 1 calc R . . H23C H 1.2702 0.3480 0.9181 0.061 Uiso 1 1 calc R . . C6 C 0.8978(10) -0.1108(5) 0.6353(6) 0.063(3) Uani 1 1 d . . . H6 H 0.8624 -0.1292 0.5805 0.076 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 0.0273(12) 0.0225(9) 0.0437(11) -0.0017(7) 0.0127(7) -0.0001(7) O3 0.024(3) 0.013(2) 0.048(3) -0.0017(16) 0.0139(19) 0.0017(18) O1 0.027(3) 0.015(2) 0.058(3) -0.0025(18) 0.013(2) 0.002(2) O4 0.025(3) 0.028(2) 0.036(2) -0.0002(17) 0.0091(18) -0.003(2) O2 0.030(4) 0.039(3) 0.103(4) -0.018(3) 0.019(3) 0.001(3) C18 0.021(4) 0.029(3) 0.040(4) 0.007(3) 0.011(3) 0.000(3) C15 0.028(4) 0.028(3) 0.029(3) 0.000(2) 0.009(3) 0.010(3) C16 0.019(4) 0.021(3) 0.041(4) -0.003(2) 0.008(3) 0.001(3) C14 0.021(4) 0.018(3) 0.039(3) -0.004(2) 0.006(3) -0.003(3) C11 0.038(5) 0.025(3) 0.040(4) -0.001(3) 0.005(3) -0.010(3) C3 0.029(4) 0.024(3) 0.048(4) -0.003(3) 0.006(3) 0.014(3) C30 0.036(5) 0.047(4) 0.043(4) -0.011(3) 0.008(3) -0.012(4) C12 0.031(5) 0.026(3) 0.031(3) -0.003(2) 0.010(3) 0.006(3) C25 0.034(4) 0.022(3) 0.053(4) -0.008(3) 0.009(3) -0.002(3) C10 0.026(4) 0.026(3) 0.037(4) -0.005(2) 0.006(3) -0.004(3) C17 0.024(4) 0.029(3) 0.041(4) 0.002(3) 0.012(3) -0.003(3) C19 0.033(4) 0.020(3) 0.035(3) -0.005(2) 0.006(3) 0.007(3) C4 0.040(5) 0.030(4) 0.060(5) -0.002(3) 0.018(3) 0.010(3) C8 0.023(4) 0.023(3) 0.072(5) -0.002(3) 0.016(3) 0.006(3) C2 0.040(5) 0.023(3) 0.057(4) 0.000(3) 0.015(3) 0.005(3) C20 0.019(4) 0.021(3) 0.040(3) -0.002(3) 0.004(3) 0.001(3) C13 0.023(4) 0.019(3) 0.036(3) -0.001(2) 0.009(3) 0.005(3) C32 0.032(5) 0.037(4) 0.055(4) -0.004(3) 0.002(3) -0.005(3) C1 0.021(5) 0.024(3) 0.061(4) -0.005(3) 0.002(3) 0.004(4) C29 0.029(4) 0.025(3) 0.037(3) -0.001(3) 0.007(3) 0.004(3) C28 0.027(4) 0.039(4) 0.045(4) -0.002(3) 0.011(3) 0.003(3) C9 0.024(4) 0.018(3) 0.040(4) -0.003(2) 0.005(3) 0.001(3) C7 0.040(5) 0.034(4) 0.080(6) -0.016(4) -0.006(5) 0.000(4) C26 0.038(5) 0.033(4) 0.050(4) -0.004(3) 0.009(3) -0.004(3) C27 0.033(5) 0.033(3) 0.046(4) 0.002(3) 0.011(3) -0.006(3) C21 0.025(4) 0.019(3) 0.053(4) 0.002(3) 0.009(3) -0.007(3) C24 0.027(5) 0.035(4) 0.077(5) 0.011(3) 0.007(4) 0.005(3) C22 0.029(5) 0.039(4) 0.057(4) -0.003(3) 0.016(3) -0.002(3) C31 0.039(5) 0.025(3) 0.064(5) -0.006(3) 0.005(3) 0.006(3) C5 0.076(7) 0.045(4) 0.049(5) 0.003(4) 0.024(4) 0.037(5) C23 0.035(5) 0.027(4) 0.065(5) -0.005(3) 0.022(3) -0.002(3) C6 0.073(7) 0.051(5) 0.060(6) -0.021(4) -0.009(5) 0.025(5) _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 O4 1.607(5) . ? P1 O3 1.629(4) . ? P1 O1 1.682(4) . ? O3 C9 1.441(7) . ? O1 C1 1.345(9) . ? O4 C15 1.406(8) . ? O2 C1 1.203(9) . ? C18 C17 1.385(8) . ? C18 C19 1.403(9) . ? C18 C28 1.508(9) . ? C15 C20 1.404(8) . ? C15 C16 1.411(9) . ? C16 C17 1.377(9) . ? C16 C29 1.558(8) . ? C14 C9 1.387(9) . ? C14 C13 1.419(8) . ? C14 C20 1.512(9) . ? C11 C12 1.380(10) . ? C11 C10 1.404(9) . ? C11 H11 0.9500 . ? C3 C8 1.401(10) . ? C3 C4 1.404(10) . ? C3 C2 1.504(8) . ? C30 C29 1.528(10) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C12 C13 1.378(9) . ? C12 C25 1.535(8) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C10 C9 1.397(9) . ? C10 C21 1.526(10) . ? C17 H17 0.9500 . ? C19 C20 1.392(10) . ? C19 C27 1.527(7) . ? C4 C5 1.362(9) . ? C4 H4 0.9500 . ? C8 C7 1.363(9) . ? C8 H8 0.9500 . ? C2 C1 1.515(8) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C13 C26 1.505(10) . ? C32 C29 1.531(10) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C29 C31 1.551(8) . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C7 C6 1.374(13) . ? C7 H7 0.9500 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C21 C22 1.518(8) . ? C21 C23 1.523(9) . ? C21 C24 1.553(8) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C5 C6 1.380(13) . ? C5 H5 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C6 H6 0.9500 . ? 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 O4 P1 O3 102.4(2) . . ? O4 P1 O1 98.7(2) . . ? O3 P1 O1 92.92(19) . . ? C9 O3 P1 113.3(3) . . ? C1 O1 P1 116.8(4) . . ? C15 O4 P1 123.8(3) . . ? C17 C18 C19 119.0(6) . . ? C17 C18 C28 121.2(6) . . ? C19 C18 C28 119.7(5) . . ? C20 C15 O4 117.0(6) . . ? C20 C15 C16 123.0(6) . . ? O4 C15 C16 120.0(5) . . ? C17 C16 C15 113.7(5) . . ? C17 C16 C29 119.2(6) . . ? C15 C16 C29 127.1(6) . . ? C9 C14 C13 117.6(6) . . ? C9 C14 C20 119.5(5) . . ? C13 C14 C20 122.8(6) . . ? C12 C11 C10 122.2(6) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C8 C3 C4 116.5(6) . . ? C8 C3 C2 121.0(7) . . ? C4 C3 C2 122.4(7) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C13 C12 C11 121.6(6) . . ? C13 C12 C25 120.3(6) . . ? C11 C12 C25 118.0(6) . . ? C12 C25 H25A 109.5 . . ? C12 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C12 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C9 C10 C11 114.5(6) . . ? C9 C10 C21 123.7(5) . . ? C11 C10 C21 121.8(6) . . ? C16 C17 C18 125.9(6) . . ? C16 C17 H17 117.1 . . ? C18 C17 H17 117.1 . . ? C20 C19 C18 118.0(5) . . ? C20 C19 C27 122.8(6) . . ? C18 C19 C27 118.9(6) . . ? C5 C4 C3 121.5(7) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C7 C8 C3 121.2(8) . . ? C7 C8 H8 119.4 . . ? C3 C8 H8 119.4 . . ? C3 C2 C1 110.9(5) . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.0 . . ? C19 C20 C15 120.3(6) . . ? C19 C20 C14 119.8(5) . . ? C15 C20 C14 119.9(6) . . ? C12 C13 C14 118.5(6) . . ? C12 C13 C26 120.8(5) . . ? C14 C13 C26 120.6(6) . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O2 C1 O1 121.8(6) . . ? O2 C1 C2 125.2(7) . . ? O1 C1 C2 113.0(7) . . ? C30 C29 C32 106.8(5) . . ? C30 C29 C31 108.8(6) . . ? C32 C29 C31 108.8(5) . . ? C30 C29 C16 116.6(5) . . ? C32 C29 C16 109.1(6) . . ? C31 C29 C16 106.4(4) . . ? C18 C28 H28A 109.5 . . ? C18 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C18 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C14 C9 C10 125.0(5) . . ? C14 C9 O3 115.2(5) . . ? C10 C9 O3 119.8(6) . . ? C8 C7 C6 121.4(8) . . ? C8 C7 H7 119.3 . . ? C6 C7 H7 119.3 . . ? C13 C26 H26A 109.5 . . ? C13 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C13 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C19 C27 H27A 109.5 . . ? C19 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C19 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C22 C21 C23 108.5(6) . . ? C22 C21 C10 111.3(5) . . ? C23 C21 C10 110.1(5) . . ? C22 C21 C24 106.2(5) . . ? C23 C21 C24 109.3(6) . . ? C10 C21 C24 111.2(6) . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C4 C5 C6 120.9(8) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C7 C6 C5 118.4(7) . . ? C7 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? 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 O4 P1 O3 C9 -63.4(5) . . . . ? O1 P1 O3 C9 -162.9(4) . . . . ? O4 P1 O1 C1 171.3(4) . . . . ? O3 P1 O1 C1 -85.7(4) . . . . ? O3 P1 O4 C15 -29.8(5) . . . . ? O1 P1 O4 C15 65.2(4) . . . . ? P1 O4 C15 C20 65.8(6) . . . . ? P1 O4 C15 C16 -114.3(5) . . . . ? C20 C15 C16 C17 -0.6(8) . . . . ? O4 C15 C16 C17 179.5(5) . . . . ? C20 C15 C16 C29 -177.9(5) . . . . ? O4 C15 C16 C29 2.2(9) . . . . ? C10 C11 C12 C13 4.1(9) . . . . ? C10 C11 C12 C25 -179.4(6) . . . . ? C12 C11 C10 C9 0.0(9) . . . . ? C12 C11 C10 C21 179.4(6) . . . . ? C15 C16 C17 C18 -2.3(9) . . . . ? C29 C16 C17 C18 175.2(5) . . . . ? C19 C18 C17 C16 2.8(10) . . . . ? C28 C18 C17 C16 -176.9(6) . . . . ? C17 C18 C19 C20 -0.3(9) . . . . ? C28 C18 C19 C20 179.5(5) . . . . ? C17 C18 C19 C27 -175.2(6) . . . . ? C28 C18 C19 C27 4.6(9) . . . . ? C8 C3 C4 C5 2.1(9) . . . . ? C2 C3 C4 C5 178.2(6) . . . . ? C4 C3 C8 C7 -2.3(9) . . . . ? C2 C3 C8 C7 -178.5(6) . . . . ? C8 C3 C2 C1 -131.1(7) . . . . ? C4 C3 C2 C1 52.9(8) . . . . ? C18 C19 C20 C15 -2.5(9) . . . . ? C27 C19 C20 C15 172.2(5) . . . . ? C18 C19 C20 C14 177.8(5) . . . . ? C27 C19 C20 C14 -7.5(9) . . . . ? O4 C15 C20 C19 -177.1(5) . . . . ? C16 C15 C20 C19 3.0(9) . . . . ? O4 C15 C20 C14 2.6(8) . . . . ? C16 C15 C20 C14 -177.3(5) . . . . ? C9 C14 C20 C19 118.5(7) . . . . ? C13 C14 C20 C19 -56.7(8) . . . . ? C9 C14 C20 C15 -61.2(7) . . . . ? C13 C14 C20 C15 123.6(6) . . . . ? C11 C12 C13 C14 -1.8(8) . . . . ? C25 C12 C13 C14 -178.1(5) . . . . ? C11 C12 C13 C26 -179.9(6) . . . . ? C25 C12 C13 C26 3.7(8) . . . . ? C9 C14 C13 C12 -4.4(8) . . . . ? C20 C14 C13 C12 170.9(5) . . . . ? C9 C14 C13 C26 173.7(6) . . . . ? C20 C14 C13 C26 -11.0(8) . . . . ? P1 O1 C1 O2 4.6(8) . . . . ? P1 O1 C1 C2 -175.0(4) . . . . ? C3 C2 C1 O2 -94.2(8) . . . . ? C3 C2 C1 O1 85.4(7) . . . . ? C17 C16 C29 C30 167.0(6) . . . . ? C15 C16 C29 C30 -15.8(9) . . . . ? C17 C16 C29 C32 45.9(7) . . . . ? C15 C16 C29 C32 -136.9(6) . . . . ? C17 C16 C29 C31 -71.4(7) . . . . ? C15 C16 C29 C31 105.8(7) . . . . ? C13 C14 C9 C10 9.0(9) . . . . ? C20 C14 C9 C10 -166.4(5) . . . . ? C13 C14 C9 O3 -172.7(5) . . . . ? C20 C14 C9 O3 11.8(8) . . . . ? C11 C10 C9 C14 -6.7(9) . . . . ? C21 C10 C9 C14 173.9(6) . . . . ? C11 C10 C9 O3 175.1(5) . . . . ? C21 C10 C9 O3 -4.3(9) . . . . ? P1 O3 C9 C14 74.7(6) . . . . ? P1 O3 C9 C10 -106.9(5) . . . . ? C3 C8 C7 C6 2.3(10) . . . . ? C9 C10 C21 C22 -171.1(6) . . . . ? C11 C10 C21 C22 9.5(8) . . . . ? C9 C10 C21 C23 68.4(7) . . . . ? C11 C10 C21 C23 -111.0(6) . . . . ? C9 C10 C21 C24 -52.9(8) . . . . ? C11 C10 C21 C24 127.7(6) . . . . ? C3 C4 C5 C6 -1.7(10) . . . . ? C8 C7 C6 C5 -1.7(11) . . . . ? C4 C5 C6 C7 1.5(11) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 25.46 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.189 _refine_diff_density_min -1.314 _refine_diff_density_rms 0.184 # Attachment '- Compound 13.CIF' data_compound13 _database_code_depnum_ccdc_archive 'CCDC 860549' #TrackingRef '- Compound 13.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; '2,4,8,10-tetra-tert-butyldibenzo[d,f][1,3,2] dioxaphosphepin-6-yl 2-phenylacetate' ; _chemical_name_common ; Phenylacetyl(3,3',5,5'-Tetra-tert-butyl-1,1'-biphenyl-2,2'-diyl)phosphite ; _chemical_melting_point 165-167 _chemical_formula_moiety 'C36 H47 O4 P' _chemical_formula_sum 'C36 H47 O4 P' _chemical_formula_weight 574.71 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 10.232(3) _cell_length_b 12.846(4) _cell_length_c 13.644(2) _cell_angle_alpha 78.15(2) _cell_angle_beta 68.93(2) _cell_angle_gamma 86.69(2) _cell_volume 1637.6(8) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 5111 _cell_measurement_theta_min 2.1334 _cell_measurement_theta_max 28.7389 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.166 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 620 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9649 _exptl_absorpt_correction_T_max 0.9881 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10448 _diffrn_reflns_av_R_equivalents 0.0605 _diffrn_reflns_av_sigmaI/netI 0.0919 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 25.34 _reflns_number_total 5799 _reflns_number_gt 4188 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _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^)+(0.1008P)^2^+0.7048P] 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 5799 _refine_ls_number_parameters 383 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1038 _refine_ls_R_factor_gt 0.0789 _refine_ls_wR_factor_ref 0.2238 _refine_ls_wR_factor_gt 0.2018 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 0.83389(9) -0.01077(7) 0.45837(6) 0.0364(3) Uani 1 1 d . . . O4 O 0.9011(2) 0.08539(16) 0.35765(15) 0.0350(5) Uani 1 1 d . . . O3 O 0.6946(2) -0.04469(16) 0.43924(15) 0.0343(5) Uani 1 1 d . . . O1 O 0.7422(2) 0.05791(17) 0.55183(16) 0.0408(6) Uani 1 1 d . . . O2 O 0.6715(3) -0.0942(2) 0.67267(18) 0.0503(6) Uani 1 1 d . . . C14 C 0.7462(3) -0.0021(2) 0.2514(2) 0.0301(7) Uani 1 1 d . . . C11 C 0.7136(3) -0.2147(3) 0.2480(2) 0.0346(7) Uani 1 1 d . . . H11 H 0.7008 -0.2869 0.2465 0.041 Uiso 1 1 calc R . . C20 C 0.7545(3) 0.1127(2) 0.2505(2) 0.0314(7) Uani 1 1 d . . . C12 C 0.7525(3) -0.1397(2) 0.1505(2) 0.0333(7) Uani 1 1 d . . . C15 C 0.8307(3) 0.1565(2) 0.2995(2) 0.0320(7) Uani 1 1 d . . . C9 C 0.7147(3) -0.0812(2) 0.3447(2) 0.0320(7) Uani 1 1 d . . . C17 C 0.7882(3) 0.3307(2) 0.2204(2) 0.0351(7) Uani 1 1 d . . . H17 H 0.8015 0.4056 0.2078 0.042 Uiso 1 1 calc R . . C1 C 0.6749(4) 0.0014(3) 0.6532(2) 0.0393(8) Uani 1 1 d . . . C19 C 0.6890(3) 0.1833(2) 0.1905(2) 0.0331(7) Uani 1 1 d . . . H19 H 0.6332 0.1551 0.1592 0.040 Uiso 1 1 calc R . . C13 C 0.7656(3) -0.0344(2) 0.1552(2) 0.0337(7) Uani 1 1 d . . . H13 H 0.7885 0.0178 0.0909 0.040 Uiso 1 1 calc R . . C32 C 0.5364(4) 0.4443(3) 0.1820(3) 0.0467(9) Uani 1 1 d . . . H32A H 0.4613 0.4024 0.2415 0.070 Uiso 1 1 calc R . . H32B H 0.4954 0.4976 0.1394 0.070 Uiso 1 1 calc R . . H32C H 0.5929 0.4801 0.2104 0.070 Uiso 1 1 calc R . . C3 C 0.7082(3) 0.1428(3) 0.7434(2) 0.0356(7) Uani 1 1 d . . . C25 C 0.7758(4) -0.1723(3) 0.0429(2) 0.0408(8) Uani 1 1 d . . . C29 C 0.6298(4) 0.3704(3) 0.1108(2) 0.0384(8) Uani 1 1 d . . . C16 C 0.8554(3) 0.2658(2) 0.2827(2) 0.0332(7) Uani 1 1 d . . . C18 C 0.7024(3) 0.2917(2) 0.1753(2) 0.0333(7) Uani 1 1 d . . . C10 C 0.6932(3) -0.1879(2) 0.3463(2) 0.0342(7) Uani 1 1 d . . . C21 C 0.6431(3) -0.2720(2) 0.4508(2) 0.0358(7) Uani 1 1 d . . . C8 C 0.6844(4) 0.2530(3) 0.7399(3) 0.0501(9) Uani 1 1 d . . . H8 H 0.6017 0.2815 0.7292 0.060 Uiso 1 1 calc R . . C33 C 0.9530(3) 0.3154(3) 0.3250(2) 0.0370(7) Uani 1 1 d . . . C31 C 0.7436(4) 0.4365(3) 0.0128(2) 0.0444(8) Uani 1 1 d . . . H31A H 0.7997 0.4770 0.0375 0.067 Uiso 1 1 calc R . . H31B H 0.6987 0.4856 -0.0301 0.067 Uiso 1 1 calc R . . H31C H 0.8043 0.3886 -0.0309 0.067 Uiso 1 1 calc R . . C34 C 1.1013(3) 0.2712(3) 0.2816(3) 0.0445(8) Uani 1 1 d . . . H34A H 1.1636 0.3036 0.3077 0.067 Uiso 1 1 calc R . . H34B H 1.1364 0.2881 0.2031 0.067 Uiso 1 1 calc R . . H34C H 1.0982 0.1939 0.3064 0.067 Uiso 1 1 calc R . . C24 C 0.7571(4) -0.2912(3) 0.5000(3) 0.0465(9) Uani 1 1 d . . . H24A H 0.7710 -0.2270 0.5237 0.070 Uiso 1 1 calc R . . H24B H 0.8449 -0.3083 0.4464 0.070 Uiso 1 1 calc R . . H24C H 0.7286 -0.3507 0.5616 0.070 Uiso 1 1 calc R . . C22 C 0.6114(4) -0.3788(3) 0.4305(3) 0.0478(9) Uani 1 1 d . . . H22A H 0.5751 -0.4294 0.4989 0.072 Uiso 1 1 calc R . . H22B H 0.6975 -0.4063 0.3837 0.072 Uiso 1 1 calc R . . H22C H 0.5413 -0.3691 0.3960 0.072 Uiso 1 1 calc R . . C4 C 0.8316(4) 0.1052(3) 0.7600(3) 0.0459(9) Uani 1 1 d . . . H4 H 0.8544 0.0325 0.7599 0.055 Uiso 1 1 calc R . . C5 C 0.9208(4) 0.1708(3) 0.7765(3) 0.0455(8) Uani 1 1 d . . . H5 H 1.0004 0.1418 0.7919 0.055 Uiso 1 1 calc R . . C36 C 0.9677(4) 0.4366(3) 0.2859(3) 0.0509(9) Uani 1 1 d . . . H36A H 1.0359 0.4644 0.3098 0.076 Uiso 1 1 calc R . . H36B H 0.8767 0.4693 0.3156 0.076 Uiso 1 1 calc R . . H36C H 0.9998 0.4534 0.2075 0.076 Uiso 1 1 calc R . . C27 C 0.6664(4) -0.1165(3) -0.0035(3) 0.0511(9) Uani 1 1 d . . . H27A H 0.6818 -0.1355 -0.0727 0.077 Uiso 1 1 calc R . . H27B H 0.6762 -0.0392 -0.0132 0.077 Uiso 1 1 calc R . . H27C H 0.5719 -0.1395 0.0462 0.077 Uiso 1 1 calc R . . C30 C 0.5396(4) 0.3128(3) 0.0696(3) 0.0508(9) Uani 1 1 d . . . H30A H 0.5989 0.2673 0.0222 0.076 Uiso 1 1 calc R . . H30B H 0.4940 0.3652 0.0298 0.076 Uiso 1 1 calc R . . H30C H 0.4680 0.2689 0.1304 0.076 Uiso 1 1 calc R . . C6 C 0.8954(4) 0.2771(3) 0.7709(3) 0.0556(10) Uani 1 1 d . . . H6 H 0.9586 0.3222 0.7802 0.067 Uiso 1 1 calc R . . C2 C 0.6087(4) 0.0711(3) 0.7331(2) 0.0452(8) Uani 1 1 d . . . H2B H 0.5364 0.1144 0.7119 0.054 Uiso 1 1 calc R . . H2A H 0.5610 0.0253 0.8040 0.054 Uiso 1 1 calc R . . C35 C 0.8978(4) 0.2932(3) 0.4474(2) 0.0481(9) Uani 1 1 d . . . H35A H 0.8997 0.2166 0.4747 0.072 Uiso 1 1 calc R . . H35B H 0.8013 0.3180 0.4739 0.072 Uiso 1 1 calc R . . H35C H 0.9568 0.3308 0.4722 0.072 Uiso 1 1 calc R . . C7 C 0.7736(4) 0.3198(3) 0.7511(3) 0.0577(10) Uani 1 1 d . . . H7 H 0.7553 0.3937 0.7457 0.069 Uiso 1 1 calc R . . C23 C 0.5070(4) -0.2370(3) 0.5304(3) 0.0491(9) Uani 1 1 d . . . H23A H 0.5262 -0.1739 0.5535 0.074 Uiso 1 1 calc R . . H23B H 0.4705 -0.2948 0.5929 0.074 Uiso 1 1 calc R . . H23C H 0.4375 -0.2198 0.4956 0.074 Uiso 1 1 calc R . . C28 C 0.9222(4) -0.1352(3) -0.0351(3) 0.0516(9) Uani 1 1 d . . . H28A H 0.9923 -0.1696 -0.0061 0.077 Uiso 1 1 calc R . . H28B H 0.9307 -0.0578 -0.0448 0.077 Uiso 1 1 calc R . . H28C H 0.9377 -0.1544 -0.1042 0.077 Uiso 1 1 calc R . . C26 C 0.7589(5) -0.2907(3) 0.0541(3) 0.0595(11) Uani 1 1 d . . . H26A H 0.7744 -0.3070 -0.0162 0.089 Uiso 1 1 calc R . . H26B H 0.6639 -0.3136 0.1029 0.089 Uiso 1 1 calc R . . H26C H 0.8273 -0.3283 0.0830 0.089 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 0.0392(5) 0.0353(5) 0.0393(4) -0.0090(3) -0.0183(4) -0.0014(4) O4 0.0363(13) 0.0322(12) 0.0420(11) -0.0082(9) -0.0201(9) 0.0000(9) O3 0.0376(13) 0.0355(12) 0.0333(10) -0.0085(8) -0.0154(9) -0.0026(10) O1 0.0466(15) 0.0382(13) 0.0390(11) -0.0076(9) -0.0162(10) -0.0038(11) O2 0.0550(17) 0.0427(16) 0.0529(13) -0.0057(11) -0.0207(12) -0.0009(12) C14 0.0259(16) 0.0329(17) 0.0350(14) -0.0070(12) -0.0143(12) -0.0037(13) C11 0.0341(18) 0.0328(18) 0.0398(15) -0.0086(13) -0.0149(13) -0.0067(14) C20 0.0299(17) 0.0320(17) 0.0331(14) -0.0052(12) -0.0125(12) -0.0020(13) C12 0.0290(17) 0.0340(18) 0.0382(15) -0.0098(12) -0.0110(13) -0.0058(13) C15 0.0279(16) 0.0355(18) 0.0348(14) -0.0084(12) -0.0131(12) 0.0025(13) C9 0.0285(17) 0.0379(18) 0.0328(14) -0.0098(12) -0.0126(12) -0.0025(13) C17 0.0353(18) 0.0281(17) 0.0390(15) -0.0052(12) -0.0099(13) -0.0045(14) C1 0.0384(19) 0.040(2) 0.0436(16) -0.0067(14) -0.0199(14) -0.0048(15) C19 0.0331(17) 0.0338(18) 0.0335(14) -0.0060(12) -0.0126(13) -0.0056(14) C13 0.0306(17) 0.0347(18) 0.0365(15) -0.0046(12) -0.0131(13) -0.0050(14) C32 0.049(2) 0.042(2) 0.0467(17) -0.0011(14) -0.0177(16) 0.0014(16) C3 0.0369(19) 0.0391(19) 0.0290(13) -0.0080(12) -0.0085(13) -0.0012(14) C25 0.046(2) 0.040(2) 0.0352(15) -0.0114(13) -0.0088(14) -0.0127(16) C29 0.043(2) 0.0327(18) 0.0425(16) -0.0002(13) -0.0217(14) -0.0049(15) C16 0.0311(17) 0.0324(18) 0.0377(15) -0.0086(12) -0.0128(13) -0.0029(13) C18 0.0322(17) 0.0331(18) 0.0346(14) -0.0038(12) -0.0129(13) -0.0022(13) C10 0.0317(17) 0.0315(18) 0.0392(15) -0.0049(12) -0.0128(13) -0.0046(13) C21 0.0382(19) 0.0330(18) 0.0380(15) -0.0024(12) -0.0172(13) -0.0046(14) C8 0.045(2) 0.056(2) 0.0490(18) -0.0113(16) -0.0167(16) 0.0001(18) C33 0.0357(18) 0.0349(18) 0.0446(16) -0.0109(13) -0.0168(14) -0.0042(14) C31 0.051(2) 0.038(2) 0.0426(17) -0.0035(14) -0.0172(16) -0.0043(16) C34 0.0329(19) 0.054(2) 0.0521(18) -0.0185(16) -0.0169(15) -0.0060(16) C24 0.050(2) 0.040(2) 0.0519(18) -0.0004(15) -0.0248(16) -0.0052(17) C22 0.063(3) 0.036(2) 0.0459(17) -0.0005(14) -0.0236(17) -0.0129(18) C4 0.044(2) 0.045(2) 0.0465(17) -0.0097(15) -0.0128(15) -0.0031(17) C5 0.0335(19) 0.043(2) 0.064(2) -0.0112(16) -0.0222(16) -0.0044(16) C36 0.057(2) 0.037(2) 0.069(2) -0.0090(16) -0.0337(19) -0.0134(18) C27 0.048(2) 0.061(3) 0.0462(18) -0.0118(16) -0.0164(16) -0.0121(19) C30 0.055(2) 0.046(2) 0.062(2) -0.0014(17) -0.0371(19) -0.0032(18) C6 0.045(2) 0.061(3) 0.062(2) -0.0222(18) -0.0134(18) -0.014(2) C2 0.044(2) 0.053(2) 0.0397(16) -0.0112(15) -0.0141(15) -0.0019(17) C35 0.044(2) 0.057(2) 0.0472(18) -0.0169(16) -0.0152(16) -0.0155(18) C7 0.053(2) 0.036(2) 0.080(3) -0.0257(18) -0.012(2) -0.0030(18) C23 0.043(2) 0.052(2) 0.0431(17) -0.0010(15) -0.0086(15) -0.0092(17) C28 0.047(2) 0.058(2) 0.0468(18) -0.0184(16) -0.0076(16) -0.0094(18) C26 0.080(3) 0.051(2) 0.0474(19) -0.0155(16) -0.0154(19) -0.020(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 O4 1.615(2) . ? P1 O3 1.635(2) . ? P1 O1 1.671(2) . ? O4 C15 1.421(4) . ? O3 C9 1.404(3) . ? O1 C1 1.370(4) . ? O2 C1 1.203(4) . ? C14 C13 1.401(4) . ? C14 C9 1.403(4) . ? C14 C20 1.479(4) . ? C11 C10 1.393(4) . ? C11 C12 1.412(4) . ? C11 H11 0.9500 . ? C20 C15 1.396(4) . ? C20 C19 1.400(4) . ? C12 C13 1.383(4) . ? C12 C25 1.542(4) . ? C15 C16 1.399(4) . ? C9 C10 1.395(4) . ? C17 C16 1.398(4) . ? C17 C18 1.402(4) . ? C17 H17 0.9500 . ? C1 C2 1.499(5) . ? C19 C18 1.373(4) . ? C19 H19 0.9500 . ? C13 H13 0.9500 . ? C32 C29 1.538(5) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C3 C4 1.403(5) . ? C3 C8 1.416(5) . ? C3 C2 1.473(5) . ? C25 C26 1.511(5) . ? C25 C28 1.527(5) . ? C25 C27 1.549(5) . ? C29 C30 1.530(5) . ? C29 C18 1.538(4) . ? C29 C31 1.546(4) . ? C16 C33 1.542(4) . ? C10 C21 1.539(4) . ? C21 C22 1.528(4) . ? C21 C24 1.528(5) . ? C21 C23 1.537(5) . ? C8 C7 1.356(5) . ? C8 H8 0.9500 . ? C33 C35 1.528(4) . ? C33 C36 1.536(5) . ? C33 C34 1.538(5) . ? C31 H31A 0.9800 . ? C31 H31B 0.9800 . ? C31 H31C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C4 C5 1.382(5) . ? C4 H4 0.9500 . ? C5 C6 1.366(5) . ? C5 H5 0.9500 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? C6 C7 1.424(6) . ? C6 H6 0.9500 . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C35 H35A 0.9800 . ? C35 H35B 0.9800 . ? C35 H35C 0.9800 . ? C7 H7 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 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 O4 P1 O3 102.74(11) . . ? O4 P1 O1 100.39(12) . . ? O3 P1 O1 93.28(11) . . ? C15 O4 P1 127.87(19) . . ? C9 O3 P1 117.60(18) . . ? C1 O1 P1 117.4(2) . . ? C13 C14 C9 117.6(3) . . ? C13 C14 C20 118.9(2) . . ? C9 C14 C20 123.5(2) . . ? C10 C11 C12 123.2(3) . . ? C10 C11 H11 118.4 . . ? C12 C11 H11 118.4 . . ? C15 C20 C19 117.5(3) . . ? C15 C20 C14 124.6(3) . . ? C19 C20 C14 117.8(2) . . ? C13 C12 C11 117.4(3) . . ? C13 C12 C25 120.8(3) . . ? C11 C12 C25 121.8(3) . . ? C20 C15 C16 123.1(3) . . ? C20 C15 O4 117.7(3) . . ? C16 C15 O4 118.6(3) . . ? C10 C9 C14 122.9(3) . . ? C10 C9 O3 121.5(2) . . ? C14 C9 O3 115.4(3) . . ? C16 C17 C18 123.7(3) . . ? C16 C17 H17 118.1 . . ? C18 C17 H17 118.1 . . ? O2 C1 O1 121.5(3) . . ? O2 C1 C2 125.5(3) . . ? O1 C1 C2 113.0(3) . . ? C18 C19 C20 122.4(3) . . ? C18 C19 H19 118.8 . . ? C20 C19 H19 118.8 . . ? C12 C13 C14 122.3(3) . . ? C12 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C29 C32 H32A 109.5 . . ? C29 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C29 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? C4 C3 C8 115.7(3) . . ? C4 C3 C2 121.7(3) . . ? C8 C3 C2 122.6(3) . . ? C26 C25 C28 110.0(3) . . ? C26 C25 C12 112.8(3) . . ? C28 C25 C12 108.7(3) . . ? C26 C25 C27 107.5(3) . . ? C28 C25 C27 108.8(3) . . ? C12 C25 C27 108.9(3) . . ? C30 C29 C18 111.7(3) . . ? C30 C29 C32 108.9(3) . . ? C18 C29 C32 109.5(2) . . ? C30 C29 C31 108.0(3) . . ? C18 C29 C31 108.6(3) . . ? C32 C29 C31 110.0(3) . . ? C17 C16 C15 115.6(3) . . ? C17 C16 C33 120.2(3) . . ? C15 C16 C33 124.2(3) . . ? C19 C18 C17 117.4(3) . . ? C19 C18 C29 123.1(3) . . ? C17 C18 C29 119.5(3) . . ? C11 C10 C9 116.5(3) . . ? C11 C10 C21 120.8(3) . . ? C9 C10 C21 122.6(3) . . ? C22 C21 C24 107.0(3) . . ? C22 C21 C23 106.9(3) . . ? C24 C21 C23 110.7(3) . . ? C22 C21 C10 111.4(2) . . ? C24 C21 C10 110.2(3) . . ? C23 C21 C10 110.5(3) . . ? C7 C8 C3 123.3(4) . . ? C7 C8 H8 118.3 . . ? C3 C8 H8 118.3 . . ? C35 C33 C36 107.6(3) . . ? C35 C33 C34 110.4(3) . . ? C36 C33 C34 106.2(3) . . ? C35 C33 C16 111.1(2) . . ? C36 C33 C16 111.9(3) . . ? C34 C33 C16 109.5(3) . . ? C29 C31 H31A 109.5 . . ? C29 C31 H31B 109.5 . . ? H31A C31 H31B 109.5 . . ? C29 C31 H31C 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C5 C4 C3 122.0(3) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C6 C5 C4 120.5(3) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C5 C6 C7 119.6(3) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C3 C2 C1 114.1(3) . . ? C3 C2 H2B 108.7 . . ? C1 C2 H2B 108.7 . . ? C3 C2 H2A 108.7 . . ? C1 C2 H2A 108.7 . . ? H2B C2 H2A 107.6 . . ? C33 C35 H35A 109.5 . . ? C33 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C33 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C8 C7 C6 118.7(4) . . ? C8 C7 H7 120.6 . . ? C6 C7 H7 120.6 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C25 C28 H28A 109.5 . . ? C25 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C25 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 O3 P1 O4 C15 27.4(2) . . . . ? O1 P1 O4 C15 -68.4(2) . . . . ? O4 P1 O3 C9 61.1(2) . . . . ? O1 P1 O3 C9 162.5(2) . . . . ? O4 P1 O1 C1 -176.4(2) . . . . ? O3 P1 O1 C1 80.0(2) . . . . ? C13 C14 C20 C15 -132.9(3) . . . . ? C9 C14 C20 C15 49.5(4) . . . . ? C13 C14 C20 C19 42.7(4) . . . . ? C9 C14 C20 C19 -134.9(3) . . . . ? C10 C11 C12 C13 -2.3(5) . . . . ? C10 C11 C12 C25 179.3(3) . . . . ? C19 C20 C15 C16 -6.5(4) . . . . ? C14 C20 C15 C16 169.2(3) . . . . ? C19 C20 C15 O4 -178.1(2) . . . . ? C14 C20 C15 O4 -2.4(4) . . . . ? P1 O4 C15 C20 -58.5(3) . . . . ? P1 O4 C15 C16 129.5(3) . . . . ? C13 C14 C9 C10 -4.3(5) . . . . ? C20 C14 C9 C10 173.3(3) . . . . ? C13 C14 C9 O3 -179.3(3) . . . . ? C20 C14 C9 O3 -1.7(4) . . . . ? P1 O3 C9 C10 108.7(3) . . . . ? P1 O3 C9 C14 -76.3(3) . . . . ? P1 O1 C1 O2 -6.2(4) . . . . ? P1 O1 C1 C2 173.9(2) . . . . ? C15 C20 C19 C18 2.8(4) . . . . ? C14 C20 C19 C18 -173.2(3) . . . . ? C11 C12 C13 C14 2.1(5) . . . . ? C25 C12 C13 C14 -179.5(3) . . . . ? C9 C14 C13 C12 1.0(5) . . . . ? C20 C14 C13 C12 -176.7(3) . . . . ? C13 C12 C25 C26 179.2(3) . . . . ? C11 C12 C25 C26 -2.5(5) . . . . ? C13 C12 C25 C28 56.9(4) . . . . ? C11 C12 C25 C28 -124.8(3) . . . . ? C13 C12 C25 C27 -61.5(4) . . . . ? C11 C12 C25 C27 116.8(3) . . . . ? C18 C17 C16 C15 -0.7(4) . . . . ? C18 C17 C16 C33 177.4(3) . . . . ? C20 C15 C16 C17 5.4(4) . . . . ? O4 C15 C16 C17 176.9(2) . . . . ? C20 C15 C16 C33 -172.6(3) . . . . ? O4 C15 C16 C33 -1.0(4) . . . . ? C20 C19 C18 C17 1.6(4) . . . . ? C20 C19 C18 C29 -179.3(3) . . . . ? C16 C17 C18 C19 -2.7(5) . . . . ? C16 C17 C18 C29 178.2(3) . . . . ? C30 C29 C18 C19 1.6(4) . . . . ? C32 C29 C18 C19 122.4(3) . . . . ? C31 C29 C18 C19 -117.5(3) . . . . ? C30 C29 C18 C17 -179.3(3) . . . . ? C32 C29 C18 C17 -58.5(4) . . . . ? C31 C29 C18 C17 61.6(4) . . . . ? C12 C11 C10 C9 -0.7(5) . . . . ? C12 C11 C10 C21 176.6(3) . . . . ? C14 C9 C10 C11 4.1(5) . . . . ? O3 C9 C10 C11 178.8(3) . . . . ? C14 C9 C10 C21 -173.2(3) . . . . ? O3 C9 C10 C21 1.5(5) . . . . ? C11 C10 C21 C22 -4.1(4) . . . . ? C9 C10 C21 C22 173.0(3) . . . . ? C11 C10 C21 C24 114.6(3) . . . . ? C9 C10 C21 C24 -68.3(4) . . . . ? C11 C10 C21 C23 -122.8(3) . . . . ? C9 C10 C21 C23 54.3(4) . . . . ? C4 C3 C8 C7 0.4(5) . . . . ? C2 C3 C8 C7 178.8(3) . . . . ? C17 C16 C33 C35 117.8(3) . . . . ? C15 C16 C33 C35 -64.3(4) . . . . ? C17 C16 C33 C36 -2.5(4) . . . . ? C15 C16 C33 C36 175.4(3) . . . . ? C17 C16 C33 C34 -120.0(3) . . . . ? C15 C16 C33 C34 57.9(4) . . . . ? C8 C3 C4 C5 2.7(4) . . . . ? C2 C3 C4 C5 -175.8(3) . . . . ? C3 C4 C5 C6 -3.9(5) . . . . ? C4 C5 C6 C7 1.9(5) . . . . ? C4 C3 C2 C1 -50.7(4) . . . . ? C8 C3 C2 C1 130.9(3) . . . . ? O2 C1 C2 C3 120.8(4) . . . . ? O1 C1 C2 C3 -59.3(4) . . . . ? C3 C8 C7 C6 -2.2(5) . . . . ? C5 C6 C7 C8 1.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.965 _refine_diff_density_max 0.430 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.072