data_1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H33 B N O2 P' _chemical_formula_weight 469.34 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' 'N' 'N' 0.0061 0.0033 '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' 'B' 'B' 0.0013 0.0007 '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' _cell_length_a 7.7674(3) _cell_length_b 9.3961(4) _cell_length_c 10.3181(4) _cell_angle_alpha 94.823(4) _cell_angle_beta 108.859(4) _cell_angle_gamma 110.954(4) _cell_volume 648.29(4) _cell_formula_units_Z 1 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.202 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 250 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9895 _exptl_absorpt_correction_T_max 0.9921 _exptl_absorpt_process_details '(CrysAlis PRO; Agilent, 2011)' _exptl_special_details ; Absorption correction: CryAllisPro, Agilent Technologies, Empirical absorption correction using spherical harmonics, implemented in SCALE# ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Agilent Supernova Dual/Cu at zero/Atlas' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10.4933 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11094 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0563 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 30.39 _reflns_number_total 6639 _reflns_number_gt 5913 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0318P)^2^+0.1341P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _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 0.06(7) _refine_ls_number_reflns 6639 _refine_ls_number_parameters 323 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0447 _refine_ls_wR_factor_ref 0.0971 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _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 0.36511(6) 0.39418(5) 0.49991(5) 0.02043(11) Uani 1 1 d . . . O1 O 0.0025(3) 0.19138(19) 0.06554(18) 0.0383(4) Uani 1 1 d . . . O2 O 0.4542(2) 0.34700(18) 0.90683(17) 0.0356(4) Uani 1 1 d . . . N1 N 0.1394(2) 0.31741(18) 0.37302(17) 0.0223(3) Uani 1 1 d . . . B1 B 0.4623(4) 0.2426(3) 0.5699(3) 0.0279(5) Uani 1 1 d . . . H1A H 0.3630 0.1655 0.5926 0.042 Uiso 1 1 calc R . . H1B H 0.5817 0.2942 0.6527 0.042 Uiso 1 1 calc R . . H1C H 0.4908 0.1926 0.4992 0.042 Uiso 1 1 calc R . . C1 C 0.1078(3) 0.1303(2) 0.1708(2) 0.0257(4) Uani 1 1 d . . . C1N C 0.0359(3) 0.4163(2) 0.3213(2) 0.0287(5) Uani 1 1 d . . . H1N1 H -0.0004 0.4022 0.2214 0.043 Uiso 1 1 calc R . . H1N2 H 0.1222 0.5239 0.3660 0.043 Uiso 1 1 calc R . . H1N3 H -0.0820 0.3877 0.3424 0.043 Uiso 1 1 calc R . . C2 C 0.0512(3) 0.1513(2) 0.2993(2) 0.0218(4) Uani 1 1 d . . . C2O C 0.5666(4) 0.2735(3) 0.9904(3) 0.0544(8) Uani 1 1 d . . . H2O1 H 0.5073 0.2321 1.0550 0.082 Uiso 1 1 calc R . . H2O2 H 0.7009 0.3488 1.0419 0.082 Uiso 1 1 calc R . . H2O3 H 0.5674 0.1900 0.9305 0.082 Uiso 1 1 calc R . . C3 C -0.1741(3) 0.0771(2) 0.2612(2) 0.0280(4) Uani 1 1 d . . . H3A H -0.2023 0.0960 0.3434 0.042 Uiso 1 1 calc R . . H3B H -0.2242 -0.0336 0.2257 0.042 Uiso 1 1 calc R . . H3C H -0.2373 0.1222 0.1906 0.042 Uiso 1 1 calc R . . C11 C 0.0697(3) -0.0385(2) 0.1191(2) 0.0250(4) Uani 1 1 d . . . C12 C 0.2185(3) -0.0896(3) 0.1766(2) 0.0302(5) Uani 1 1 d . . . H12 H 0.3404 -0.0200 0.2445 0.036 Uiso 1 1 calc R . . C13 C 0.1867(4) -0.2442(3) 0.1335(3) 0.0401(6) Uani 1 1 d . . . H13 H 0.2876 -0.2775 0.1722 0.048 Uiso 1 1 calc R . . C14 C 0.0065(4) -0.3481(3) 0.0338(3) 0.0430(7) Uani 1 1 d . . . H14 H -0.0151 -0.4519 0.0065 0.052 Uiso 1 1 calc R . . C15 C -0.1430(4) -0.2983(3) -0.0259(3) 0.0399(6) Uani 1 1 d . . . H15 H -0.2642 -0.3678 -0.0945 0.048 Uiso 1 1 calc R . . C16 C -0.1102(4) -0.1439(3) 0.0175(2) 0.0322(5) Uani 1 1 d . . . H16 H -0.2106 -0.1105 -0.0222 0.039 Uiso 1 1 calc R . . C21 C 0.5433(3) 0.5150(2) 0.4321(2) 0.0236(4) Uani 1 1 d . . . C22 C 0.4869(3) 0.5216(2) 0.2911(2) 0.0266(4) Uani 1 1 d . . . H22 H 0.3545 0.4676 0.2303 0.032 Uiso 1 1 calc R . . C23 C 0.6285(4) 0.6090(3) 0.2403(3) 0.0320(5) Uani 1 1 d . . . H23 H 0.5902 0.6128 0.1459 0.038 Uiso 1 1 calc R . . C24 C 0.8254(3) 0.6899(3) 0.3307(3) 0.0332(5) Uani 1 1 d . . . H24 H 0.9192 0.7485 0.2969 0.040 Uiso 1 1 calc R . . C25 C 0.8833(3) 0.6841(3) 0.4712(3) 0.0335(5) Uani 1 1 d . . . H25 H 1.0158 0.7390 0.5317 0.040 Uiso 1 1 calc R . . C26 C 0.7436(3) 0.5962(2) 0.5220(2) 0.0299(5) Uani 1 1 d . . . H26 H 0.7833 0.5913 0.6161 0.036 Uiso 1 1 calc R . . C31 C 0.3572(3) 0.5388(2) 0.6265(2) 0.0211(4) Uani 1 1 d . . . C32 C 0.2694(3) 0.4924(2) 0.7236(2) 0.0223(4) Uani 1 1 d . . . C33 C 0.2713(3) 0.6069(2) 0.8198(2) 0.0309(5) Uani 1 1 d . . . H33 H 0.2167 0.5769 0.8863 0.037 Uiso 1 1 calc R . . C34 C 0.3519(4) 0.7635(3) 0.8192(2) 0.0327(5) Uani 1 1 d . . . H34 H 0.3524 0.8375 0.8852 0.039 Uiso 1 1 calc R . . C35 C 0.4321(3) 0.8102(2) 0.7201(2) 0.0288(5) Uani 1 1 d . . . H35 H 0.4823 0.9152 0.7168 0.035 Uiso 1 1 calc R . . C36 C 0.4364(3) 0.6984(2) 0.6258(2) 0.0258(4) Uani 1 1 d . . . H36 H 0.4931 0.7299 0.5607 0.031 Uiso 1 1 calc R . . C41 C 0.1652(3) 0.3250(2) 0.7265(2) 0.0230(4) Uani 1 1 d . . . C42 C 0.2623(3) 0.2545(2) 0.8210(2) 0.0245(4) Uani 1 1 d . . . C43 C 0.1622(3) 0.0988(2) 0.8234(2) 0.0287(5) Uani 1 1 d . . . H43 H 0.2271 0.0515 0.8858 0.034 Uiso 1 1 calc R . . C44 C -0.0342(4) 0.0152(2) 0.7323(2) 0.0330(5) Uani 1 1 d . . . H44 H -0.1001 -0.0890 0.7328 0.040 Uiso 1 1 calc R . . C45 C -0.1336(4) 0.0853(3) 0.6404(3) 0.0366(6) Uani 1 1 d . . . H45 H -0.2664 0.0296 0.5810 0.044 Uiso 1 1 calc R . . C46 C -0.0321(3) 0.2400(3) 0.6384(2) 0.0310(5) Uani 1 1 d . . . H46 H -0.0980 0.2873 0.5767 0.037 Uiso 1 1 calc R . . H1 H 0.245(4) 0.194(3) 0.200(3) 0.031(6) Uiso 1 1 d . . . H2 H 0.112(3) 0.104(2) 0.365(2) 0.009(5) Uiso 1 1 d . . . H1O H 0.006(5) 0.169(3) -0.013(3) 0.057(9) 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 0.0219(2) 0.0210(2) 0.0205(2) 0.00599(19) 0.0093(2) 0.0097(2) O1 0.0636(12) 0.0404(9) 0.0294(9) 0.0180(7) 0.0252(9) 0.0325(9) O2 0.0293(8) 0.0302(8) 0.0379(9) 0.0133(7) 0.0022(7) 0.0099(7) N1 0.0205(8) 0.0190(8) 0.0246(9) 0.0037(7) 0.0063(7) 0.0073(7) B1 0.0310(13) 0.0310(12) 0.0267(12) 0.0076(10) 0.0084(10) 0.0201(11) C1 0.0292(11) 0.0227(10) 0.0274(11) 0.0069(8) 0.0126(9) 0.0111(9) C1N 0.0270(11) 0.0261(10) 0.0324(12) 0.0065(9) 0.0068(9) 0.0141(9) C2 0.0255(10) 0.0190(9) 0.0228(10) 0.0058(8) 0.0100(8) 0.0102(8) C2O 0.0351(14) 0.0554(18) 0.0619(19) 0.0331(15) 0.0024(13) 0.0167(13) C3 0.0235(10) 0.0267(10) 0.0316(12) 0.0043(9) 0.0126(9) 0.0063(9) C11 0.0293(11) 0.0224(10) 0.0252(10) 0.0066(8) 0.0145(9) 0.0086(9) C12 0.0319(12) 0.0331(12) 0.0324(12) 0.0087(9) 0.0169(10) 0.0162(10) C13 0.0505(15) 0.0396(13) 0.0524(16) 0.0192(12) 0.0343(13) 0.0277(12) C14 0.0657(18) 0.0239(11) 0.0560(16) 0.0094(11) 0.0466(15) 0.0155(12) C15 0.0461(15) 0.0284(12) 0.0340(13) -0.0014(10) 0.0214(12) -0.0008(11) C16 0.0349(12) 0.0341(12) 0.0260(11) 0.0067(9) 0.0127(10) 0.0114(10) C21 0.0261(10) 0.0226(10) 0.0264(10) 0.0059(8) 0.0126(9) 0.0122(9) C22 0.0284(11) 0.0265(10) 0.0279(11) 0.0074(8) 0.0123(9) 0.0127(9) C23 0.0418(13) 0.0323(12) 0.0347(12) 0.0167(10) 0.0229(11) 0.0197(11) C24 0.0333(13) 0.0291(11) 0.0496(15) 0.0138(10) 0.0281(12) 0.0143(10) C25 0.0225(10) 0.0310(11) 0.0457(14) 0.0055(10) 0.0150(10) 0.0085(10) C26 0.0293(11) 0.0319(11) 0.0311(11) 0.0067(9) 0.0136(9) 0.0134(10) C31 0.0204(9) 0.0216(9) 0.0214(10) 0.0040(7) 0.0067(8) 0.0100(8) C32 0.0209(9) 0.0239(10) 0.0233(10) 0.0077(8) 0.0080(8) 0.0103(8) C33 0.0380(12) 0.0332(12) 0.0294(11) 0.0080(9) 0.0192(10) 0.0172(11) C34 0.0395(13) 0.0275(11) 0.0344(12) 0.0009(9) 0.0151(10) 0.0178(10) C35 0.0288(11) 0.0199(10) 0.0364(12) 0.0056(9) 0.0106(10) 0.0105(9) C36 0.0245(10) 0.0240(10) 0.0273(11) 0.0075(8) 0.0091(9) 0.0083(9) C41 0.0255(10) 0.0260(10) 0.0230(10) 0.0079(8) 0.0139(8) 0.0118(9) C42 0.0259(10) 0.0227(10) 0.0249(10) 0.0045(8) 0.0107(9) 0.0093(9) C43 0.0365(12) 0.0272(11) 0.0284(11) 0.0106(9) 0.0166(10) 0.0149(10) C44 0.0412(13) 0.0226(10) 0.0305(12) 0.0070(9) 0.0184(11) 0.0035(10) C45 0.0287(12) 0.0358(13) 0.0324(13) 0.0090(10) 0.0089(10) 0.0011(10) C46 0.0277(11) 0.0364(12) 0.0283(11) 0.0125(9) 0.0103(9) 0.0117(10) _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 N1 1.6615(17) . ? P1 C21 1.825(2) . ? P1 C31 1.8353(19) . ? P1 B1 1.926(2) . ? O1 C1 1.430(3) . ? O1 H1O 0.83(3) . ? O2 C42 1.361(3) . ? O2 C2O 1.424(3) . ? N1 C1N 1.461(3) . ? N1 C2 1.477(2) . ? B1 H1A 0.9600 . ? B1 H1B 0.9600 . ? B1 H1C 0.9600 . ? C1 C11 1.519(3) . ? C1 C2 1.545(3) . ? C1 H1 0.94(3) . ? C1N H1N1 0.9600 . ? C1N H1N2 0.9600 . ? C1N H1N3 0.9600 . ? C2 C3 1.530(3) . ? C2 H2 0.93(2) . ? C2O H2O1 0.9600 . ? C2O H2O2 0.9600 . ? C2O H2O3 0.9600 . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C11 C12 1.385(3) . ? C11 C16 1.386(3) . ? C12 C13 1.390(3) . ? C12 H12 0.9300 . ? C13 C14 1.376(4) . ? C13 H13 0.9300 . ? C14 C15 1.386(4) . ? C14 H14 0.9300 . ? C15 C16 1.387(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C22 1.391(3) . ? C21 C26 1.401(3) . ? C22 C23 1.399(3) . ? C22 H22 0.9300 . ? C23 C24 1.383(3) . ? C23 H23 0.9300 . ? C24 C25 1.385(3) . ? C24 H24 0.9300 . ? C25 C26 1.391(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C32 1.401(3) . ? C31 C36 1.405(3) . ? C32 C33 1.394(3) . ? C32 C41 1.498(3) . ? C33 C34 1.379(3) . ? C33 H33 0.9300 . ? C34 C35 1.385(3) . ? C34 H34 0.9300 . ? C35 C36 1.388(3) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C41 C46 1.383(3) . ? C41 C42 1.396(3) . ? C42 C43 1.396(3) . ? C43 C44 1.386(3) . ? C43 H43 0.9300 . ? C44 C45 1.388(3) . ? C44 H44 0.9300 . ? C45 C46 1.389(3) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? 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 N1 P1 C21 109.03(9) . . ? N1 P1 C31 105.28(8) . . ? C21 P1 C31 102.89(9) . . ? N1 P1 B1 114.44(10) . . ? C21 P1 B1 106.26(10) . . ? C31 P1 B1 118.13(10) . . ? C1 O1 H1O 114(2) . . ? C42 O2 C2O 117.14(18) . . ? C1N N1 C2 118.82(16) . . ? C1N N1 P1 120.73(14) . . ? C2 N1 P1 120.04(13) . . ? P1 B1 H1A 109.5 . . ? P1 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? P1 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? O1 C1 C11 113.23(17) . . ? O1 C1 C2 107.62(16) . . ? C11 C1 C2 112.08(16) . . ? O1 C1 H1 107.4(14) . . ? C11 C1 H1 109.8(14) . . ? C2 C1 H1 106.4(15) . . ? N1 C1N H1N1 109.5 . . ? N1 C1N H1N2 109.5 . . ? H1N1 C1N H1N2 109.5 . . ? N1 C1N H1N3 109.5 . . ? H1N1 C1N H1N3 109.5 . . ? H1N2 C1N H1N3 109.5 . . ? N1 C2 C3 111.45(16) . . ? N1 C2 C1 111.59(15) . . ? C3 C2 C1 112.46(17) . . ? N1 C2 H2 103.9(12) . . ? C3 C2 H2 109.5(12) . . ? C1 C2 H2 107.5(12) . . ? O2 C2O H2O1 109.5 . . ? O2 C2O H2O2 109.5 . . ? H2O1 C2O H2O2 109.5 . . ? O2 C2O H2O3 109.5 . . ? H2O1 C2O H2O3 109.5 . . ? H2O2 C2O H2O3 109.5 . . ? 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 . . ? C12 C11 C16 118.85(19) . . ? C12 C11 C1 119.01(19) . . ? C16 C11 C1 122.14(19) . . ? C11 C12 C13 120.4(2) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 120.2(2) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 120.1(2) . . ? C13 C14 H14 120.0 . . ? C15 C14 H14 120.0 . . ? C14 C15 C16 119.4(2) . . ? C14 C15 H15 120.3 . . ? C16 C15 H15 120.3 . . ? C11 C16 C15 121.1(2) . . ? C11 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C22 C21 C26 119.08(19) . . ? C22 C21 P1 121.44(15) . . ? C26 C21 P1 119.38(16) . . ? C21 C22 C23 120.3(2) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 119.9(2) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C23 C24 C25 120.3(2) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C24 C25 C26 120.0(2) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.4(2) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C32 C31 C36 118.74(17) . . ? C32 C31 P1 120.94(14) . . ? C36 C31 P1 120.31(15) . . ? C33 C32 C31 118.78(18) . . ? C33 C32 C41 117.59(18) . . ? C31 C32 C41 123.57(17) . . ? C34 C33 C32 121.8(2) . . ? C34 C33 H33 119.1 . . ? C32 C33 H33 119.1 . . ? C33 C34 C35 119.90(19) . . ? C33 C34 H34 120.1 . . ? C35 C34 H34 120.1 . . ? C34 C35 C36 119.1(2) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? C35 C36 C31 121.53(19) . . ? C35 C36 H36 119.2 . . ? C31 C36 H36 119.2 . . ? C46 C41 C42 119.15(19) . . ? C46 C41 C32 120.00(18) . . ? C42 C41 C32 120.81(18) . . ? O2 C42 C43 124.25(18) . . ? O2 C42 C41 115.66(17) . . ? C43 C42 C41 120.09(19) . . ? C44 C43 C42 119.68(19) . . ? C44 C43 H43 120.2 . . ? C42 C43 H43 120.2 . . ? C43 C44 C45 120.7(2) . . ? C43 C44 H44 119.7 . . ? C45 C44 H44 119.7 . . ? C44 C45 C46 119.1(2) . . ? C44 C45 H45 120.4 . . ? C46 C45 H45 120.4 . . ? C41 C46 C45 121.3(2) . . ? C41 C46 H46 119.4 . . ? C45 C46 H46 119.4 . . ? _diffrn_measured_fraction_theta_max 0.896 _diffrn_reflns_theta_full 30.39 _diffrn_measured_fraction_theta_full 0.896 _refine_diff_density_max 0.285 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.045 #===END data_4c _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H20 B O P' _chemical_formula_weight 318.14 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 14.5338(2) _cell_length_b 14.7098(3) _cell_length_c 16.4238(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3511.23(11) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.158 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9783 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details ; HKL SCALEPACK (Otwinowski & Minor, 1997) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius Kappa CCD diffractometer' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 37995 _diffrn_reflns_av_R_equivalents 0.054 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.48 _reflns_number_total 8043 _reflns_number_gt 6502 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_cell_refinement 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_data_reduction 'Denzo-SMN (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.7872P] 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 -0.01(8) _refine_ls_number_reflns 8043 _refine_ls_number_parameters 419 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0454 _refine_ls_wR_factor_ref 0.1160 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 0.33668(4) 1.30932(4) 0.38192(4) 0.04607(15) Uani 1 1 d . . . P2 P 0.56919(4) 0.90000(4) 0.63510(4) 0.04670(15) Uani 1 1 d . . . O1 O 0.46439(13) 1.08846(13) 0.17020(10) 0.0610(5) Uani 1 1 d . . . O2 O 0.34542(12) 0.79823(14) 0.41442(10) 0.0619(5) Uani 1 1 d . . . B1 B 0.3214(3) 1.3872(2) 0.4744(2) 0.0732(10) Uani 1 1 d . . . H1A H 0.2578 1.4039 0.4795 0.110 Uiso 1 1 calc R . . H1B H 0.3579 1.4410 0.4674 0.110 Uiso 1 1 calc R . . H1C H 0.3408 1.3559 0.5227 0.110 Uiso 1 1 calc R . . B2 B 0.6439(3) 0.9075(3) 0.7308(2) 0.0716(9) Uani 1 1 d . . . H2A H 0.6945 0.8659 0.7262 0.107 Uiso 1 1 calc R . . H2B H 0.6076 0.8922 0.7776 0.107 Uiso 1 1 calc R . . H2C H 0.6671 0.9683 0.7365 0.107 Uiso 1 1 calc R . . C1O C 0.4526(2) 1.0072(2) 0.12498(18) 0.0734(8) Uani 1 1 d . . . H1O1 H 0.3903 0.9864 0.1304 0.110 Uiso 1 1 calc R . . H1O2 H 0.4938 0.9615 0.1453 0.110 Uiso 1 1 calc R . . H1O3 H 0.4657 1.0186 0.0686 0.110 Uiso 1 1 calc R . . C1 C 0.32021(18) 1.36124(18) 0.28302(15) 0.0561(6) Uani 1 1 d . . . H1D H 0.2592 1.3878 0.2800 0.067 Uiso 1 1 calc R . . H1E H 0.3649 1.4095 0.2754 0.067 Uiso 1 1 calc R . . C2O C 0.2671(2) 0.8155(2) 0.3650(2) 0.0771(8) Uani 1 1 d . . . H2O1 H 0.2462 0.8766 0.3739 0.116 Uiso 1 1 calc R . . H2O2 H 0.2189 0.7737 0.3789 0.116 Uiso 1 1 calc R . . H2O3 H 0.2832 0.8079 0.3087 0.116 Uiso 1 1 calc R . . C2 C 0.62811(18) 0.91260(19) 0.53886(15) 0.0553(6) Uani 1 1 d . . . H2D H 0.6617 0.9696 0.5382 0.066 Uiso 1 1 calc R . . H2E H 0.6719 0.8634 0.5319 0.066 Uiso 1 1 calc R . . C11 C 0.33120(16) 1.29132(17) 0.21686(13) 0.0477(5) Uani 1 1 d . . . C12 C 0.40130(14) 1.22605(16) 0.22105(12) 0.0405(5) Uani 1 1 d . . . C13 C 0.40083(16) 1.15662(17) 0.16165(13) 0.0459(5) Uani 1 1 d . . . C14 C 0.33658(19) 1.1573(2) 0.09926(15) 0.0602(7) Uani 1 1 d . . . H14 H 0.3377 1.1118 0.0599 0.072 Uiso 1 1 calc R . . C15 C 0.27155(19) 1.2245(2) 0.09517(17) 0.0679(8) Uani 1 1 d . . . H15 H 0.2300 1.2255 0.0522 0.081 Uiso 1 1 calc R . . C16 C 0.26747(17) 1.2897(2) 0.15367(16) 0.0631(7) Uani 1 1 d . . . H16 H 0.2216 1.3338 0.1514 0.076 Uiso 1 1 calc R . . C21 C 0.47224(14) 1.23008(14) 0.28608(13) 0.0379(4) Uani 1 1 d . . . C22 C 0.45003(14) 1.26441(14) 0.36436(13) 0.0393(4) Uani 1 1 d . . . C23 C 0.51620(16) 1.26920(17) 0.42522(14) 0.0498(5) Uani 1 1 d . . . H23 H 0.5005 1.2918 0.4763 0.060 Uiso 1 1 calc R . . C24 C 0.60526(17) 1.24066(19) 0.41043(16) 0.0540(6) Uani 1 1 d . . . H24 H 0.6492 1.2433 0.4515 0.065 Uiso 1 1 calc R . . C25 C 0.62821(16) 1.20852(18) 0.33521(15) 0.0514(6) Uani 1 1 d . . . H25 H 0.6882 1.1895 0.3253 0.062 Uiso 1 1 calc R . . C26 C 0.56335(15) 1.20369(15) 0.27301(13) 0.0436(5) Uani 1 1 d . . . H26 H 0.5809 1.1826 0.2220 0.052 Uiso 1 1 calc R . . C31 C 0.26061(15) 1.21229(17) 0.38774(14) 0.0471(5) Uani 1 1 d . . . C32 C 0.28946(19) 1.13448(19) 0.42701(17) 0.0604(7) Uani 1 1 d . . . H32 H 0.3499 1.1306 0.4452 0.072 Uiso 1 1 calc R . . C33 C 0.2306(3) 1.0623(2) 0.4399(2) 0.0816(9) Uani 1 1 d . . . H33 H 0.2510 1.0108 0.4673 0.098 Uiso 1 1 calc R . . C34 C 0.1418(3) 1.0670(3) 0.4120(2) 0.0933(12) Uani 1 1 d . . . H34 H 0.1019 1.0186 0.4204 0.112 Uiso 1 1 calc R . . C35 C 0.1117(2) 1.1436(3) 0.3715(2) 0.0954(13) Uani 1 1 d . . . H35 H 0.0517 1.1461 0.3522 0.115 Uiso 1 1 calc R . . C36 C 0.16999(18) 1.2167(2) 0.35950(17) 0.0692(8) Uani 1 1 d . . . H36 H 0.1490 1.2684 0.3328 0.083 Uiso 1 1 calc R . . C41 C 0.55900(18) 0.91120(16) 0.46996(14) 0.0490(5) Uani 1 1 d . . . C42 C 0.48679(16) 0.84723(15) 0.47019(12) 0.0415(5) Uani 1 1 d . . . C43 C 0.41913(17) 0.85554(17) 0.40923(13) 0.0481(5) Uani 1 1 d . . . C44 C 0.4274(2) 0.92133(19) 0.34917(15) 0.0615(7) Uani 1 1 d . . . H44 H 0.3829 0.9256 0.3087 0.074 Uiso 1 1 calc R . . C45 C 0.5006(2) 0.98017(19) 0.34902(16) 0.0695(8) Uani 1 1 d . . . H45 H 0.5061 1.0231 0.3078 0.083 Uiso 1 1 calc R . . C46 C 0.5660(2) 0.97612(18) 0.40953(15) 0.0601(7) Uani 1 1 d . . . H46 H 0.6148 1.0170 0.4097 0.072 Uiso 1 1 calc R . . C51 C 0.48298(15) 0.77524(15) 0.53398(13) 0.0403(5) Uani 1 1 d . . . C52 C 0.51514(14) 0.79201(14) 0.61373(13) 0.0414(5) Uani 1 1 d . . . C53 C 0.51293(17) 0.72500(17) 0.67277(14) 0.0501(6) Uani 1 1 d . . . H53 H 0.5340 0.7378 0.7250 0.060 Uiso 1 1 calc R . . C54 C 0.47949(19) 0.63876(17) 0.65487(16) 0.0558(6) Uani 1 1 d . . . H54 H 0.4779 0.5938 0.6946 0.067 Uiso 1 1 calc R . . C55 C 0.44885(17) 0.62126(16) 0.57745(17) 0.0525(6) Uani 1 1 d . . . H55 H 0.4266 0.5636 0.5650 0.063 Uiso 1 1 calc R . . C56 C 0.45025(15) 0.68719(16) 0.51753(14) 0.0457(5) Uani 1 1 d . . . H56 H 0.4292 0.6731 0.4656 0.055 Uiso 1 1 calc R . . C61 C 0.47814(17) 0.98404(15) 0.63663(14) 0.0483(5) Uani 1 1 d . . . C62 C 0.4948(2) 1.07287(18) 0.61216(17) 0.0697(8) Uani 1 1 d . . . H62 H 0.5518 1.0885 0.5906 0.084 Uiso 1 1 calc R . . C63 C 0.4274(3) 1.1377(2) 0.6197(2) 0.0884(11) Uani 1 1 d . . . H63 H 0.4388 1.1969 0.6024 0.106 Uiso 1 1 calc R . . C64 C 0.3447(3) 1.1162(3) 0.6520(2) 0.0904(12) Uani 1 1 d . . . H64 H 0.2994 1.1607 0.6562 0.109 Uiso 1 1 calc R . . C65 C 0.3264(2) 1.0291(3) 0.6787(2) 0.0886(11) Uani 1 1 d . . . H65 H 0.2700 1.0150 0.7023 0.106 Uiso 1 1 calc R . . C66 C 0.3937(2) 0.9627(2) 0.66984(18) 0.0656(7) Uani 1 1 d . . . H66 H 0.3817 0.9034 0.6864 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0455(3) 0.0471(3) 0.0457(3) -0.0040(3) 0.0055(3) 0.0049(3) P2 0.0501(3) 0.0471(3) 0.0429(3) -0.0030(3) -0.0049(3) -0.0024(3) O1 0.0749(12) 0.0594(11) 0.0488(9) -0.0130(8) -0.0094(8) 0.0156(9) O2 0.0613(10) 0.0763(12) 0.0479(9) 0.0053(9) -0.0117(8) -0.0089(10) B1 0.087(2) 0.061(2) 0.072(2) -0.0202(17) 0.0233(19) 0.0003(18) B2 0.071(2) 0.084(2) 0.0598(18) -0.0131(18) -0.0236(16) -0.0003(19) C1O 0.091(2) 0.0686(18) 0.0610(17) -0.0211(15) 0.0016(16) 0.0041(15) C1 0.0559(15) 0.0529(15) 0.0595(15) 0.0087(12) 0.0050(12) 0.0183(12) C2O 0.0735(18) 0.089(2) 0.0693(18) -0.0067(18) -0.0234(16) 0.0027(16) C2 0.0512(14) 0.0582(15) 0.0565(14) -0.0031(12) 0.0052(11) -0.0136(12) C11 0.0453(12) 0.0563(14) 0.0416(11) 0.0095(10) 0.0004(10) 0.0056(11) C12 0.0394(11) 0.0496(12) 0.0325(10) 0.0062(9) 0.0015(8) -0.0006(9) C13 0.0460(12) 0.0564(14) 0.0352(11) -0.0001(10) -0.0012(9) -0.0025(10) C14 0.0619(16) 0.0760(18) 0.0427(13) -0.0034(12) -0.0107(12) -0.0092(14) C15 0.0519(14) 0.104(2) 0.0474(15) 0.0097(16) -0.0152(12) -0.0079(15) C16 0.0448(13) 0.091(2) 0.0535(15) 0.0203(15) -0.0050(11) 0.0127(13) C21 0.0363(10) 0.0386(11) 0.0388(11) 0.0046(9) 0.0008(8) -0.0006(9) C22 0.0407(11) 0.0403(11) 0.0369(10) 0.0003(9) 0.0002(9) -0.0029(8) C23 0.0528(13) 0.0567(14) 0.0400(12) -0.0035(10) -0.0048(10) -0.0084(11) C24 0.0467(13) 0.0636(16) 0.0518(14) 0.0051(12) -0.0159(11) -0.0076(11) C25 0.0343(11) 0.0601(16) 0.0597(14) 0.0091(12) -0.0016(10) -0.0017(10) C26 0.0409(11) 0.0477(13) 0.0423(11) 0.0023(10) 0.0046(9) 0.0001(10) C31 0.0400(11) 0.0615(15) 0.0400(11) -0.0101(11) 0.0055(9) -0.0029(10) C32 0.0580(16) 0.0610(17) 0.0622(16) 0.0019(13) 0.0028(13) -0.0098(13) C33 0.092(2) 0.070(2) 0.083(2) 0.0046(17) 0.0159(19) -0.0241(18) C34 0.097(3) 0.115(3) 0.068(2) -0.021(2) 0.0223(19) -0.054(2) C35 0.0535(17) 0.163(4) 0.070(2) -0.026(3) 0.0057(16) -0.037(2) C36 0.0496(14) 0.098(2) 0.0599(16) -0.0031(16) 0.0011(13) 0.0006(15) C41 0.0615(14) 0.0452(13) 0.0404(11) -0.0025(10) 0.0096(11) -0.0044(11) C42 0.0511(12) 0.0411(11) 0.0322(10) -0.0023(9) 0.0043(9) 0.0023(10) C43 0.0589(14) 0.0480(13) 0.0376(11) -0.0014(10) 0.0020(10) 0.0027(11) C44 0.0800(18) 0.0652(17) 0.0392(12) 0.0070(11) -0.0048(12) 0.0061(15) C45 0.108(2) 0.0527(15) 0.0478(15) 0.0137(12) 0.0122(15) 0.0034(16) C46 0.0807(18) 0.0487(14) 0.0508(14) 0.0048(11) 0.0116(14) -0.0112(13) C51 0.0411(11) 0.0402(11) 0.0394(11) -0.0005(9) 0.0046(9) 0.0010(9) C52 0.0426(11) 0.0413(12) 0.0403(11) 0.0003(9) 0.0005(9) 0.0036(9) C53 0.0540(13) 0.0541(14) 0.0421(12) 0.0061(10) -0.0016(10) 0.0067(11) C54 0.0646(15) 0.0459(14) 0.0568(15) 0.0136(11) 0.0092(13) 0.0055(12) C55 0.0563(15) 0.0364(12) 0.0649(15) 0.0000(11) 0.0128(12) 0.0014(10) C56 0.0505(13) 0.0412(12) 0.0454(12) -0.0060(10) 0.0033(10) 0.0008(10) C61 0.0620(14) 0.0442(12) 0.0385(11) -0.0072(10) -0.0088(11) 0.0005(11) C62 0.101(2) 0.0528(15) 0.0556(15) -0.0025(12) 0.0034(15) 0.0036(15) C63 0.146(3) 0.0589(18) 0.0603(18) -0.0035(15) -0.008(2) 0.025(2) C64 0.112(3) 0.085(3) 0.073(2) -0.0246(18) -0.030(2) 0.052(2) C65 0.071(2) 0.099(3) 0.095(2) -0.027(2) -0.0033(18) 0.0235(19) C66 0.0655(17) 0.0570(16) 0.0742(18) -0.0125(14) -0.0001(14) 0.0037(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 C22 1.798(2) . ? P1 C31 1.808(2) . ? P1 C1 1.811(3) . ? P1 B1 1.916(3) . ? P2 C52 1.807(2) . ? P2 C2 1.807(2) . ? P2 C61 1.811(2) . ? P2 B2 1.913(3) . ? O1 C13 1.371(3) . ? O1 C1O 1.418(3) . ? O2 C43 1.366(3) . ? O2 C2O 1.421(3) . ? B1 H1A 0.9600 . ? B1 H1B 0.9600 . ? B1 H1C 0.9600 . ? B2 H2A 0.9600 . ? B2 H2B 0.9600 . ? B2 H2C 0.9600 . ? C1O H1O1 0.9600 . ? C1O H1O2 0.9600 . ? C1O H1O3 0.9600 . ? C1 C11 1.505(4) . ? C1 H1D 0.9700 . ? C1 H1E 0.9700 . ? C2O H2O1 0.9600 . ? C2O H2O2 0.9600 . ? C2O H2O3 0.9600 . ? C2 C41 1.513(3) . ? C2 H2D 0.9700 . ? C2 H2E 0.9700 . ? C11 C16 1.391(3) . ? C11 C12 1.402(3) . ? C12 C13 1.412(3) . ? C12 C21 1.486(3) . ? C13 C14 1.386(3) . ? C14 C15 1.369(4) . ? C14 H14 0.9300 . ? C15 C16 1.360(4) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C26 1.396(3) . ? C21 C22 1.419(3) . ? C22 C23 1.389(3) . ? C23 C24 1.382(4) . ? C23 H23 0.9300 . ? C24 C25 1.364(4) . ? C24 H24 0.9300 . ? C25 C26 1.392(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C32 1.379(4) . ? C31 C36 1.398(3) . ? C32 C33 1.380(4) . ? C32 H32 0.9300 . ? C33 C34 1.370(5) . ? C33 H33 0.9300 . ? C34 C35 1.379(6) . ? C34 H34 0.9300 . ? C35 C36 1.382(5) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C41 C46 1.381(3) . ? C41 C42 1.410(3) . ? C42 C43 1.409(3) . ? C42 C51 1.491(3) . ? C43 C44 1.387(3) . ? C44 C45 1.371(4) . ? C44 H44 0.9300 . ? C45 C46 1.377(4) . ? C45 H45 0.9300 . ? C46 H46 0.9300 . ? C51 C56 1.406(3) . ? C51 C52 1.412(3) . ? C52 C53 1.383(3) . ? C53 C54 1.390(4) . ? C53 H53 0.9300 . ? C54 C55 1.372(4) . ? C54 H54 0.9300 . ? C55 C56 1.382(3) . ? C55 H55 0.9300 . ? C56 H56 0.9300 . ? C61 C66 1.379(4) . ? C61 C62 1.388(4) . ? C62 C63 1.373(5) . ? C62 H62 0.9300 . ? C63 C64 1.352(6) . ? C63 H63 0.9300 . ? C64 C65 1.381(6) . ? C64 H64 0.9300 . ? C65 C66 1.389(4) . ? C65 H65 0.9300 . ? C66 H66 0.9300 . ? 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 C22 P1 C31 106.18(10) . . ? C22 P1 C1 97.60(11) . . ? C31 P1 C1 107.42(12) . . ? C22 P1 B1 116.96(15) . . ? C31 P1 B1 111.06(14) . . ? C1 P1 B1 116.33(15) . . ? C52 P2 C2 97.25(11) . . ? C52 P2 C61 106.57(10) . . ? C2 P2 C61 106.76(12) . . ? C52 P2 B2 117.22(15) . . ? C2 P2 B2 116.32(15) . . ? C61 P2 B2 111.33(14) . . ? C13 O1 C1O 118.8(2) . . ? C43 O2 C2O 118.8(2) . . ? P1 B1 H1A 109.5 . . ? P1 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? P1 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? P2 B2 H2A 109.5 . . ? P2 B2 H2B 109.5 . . ? H2A B2 H2B 109.5 . . ? P2 B2 H2C 109.5 . . ? H2A B2 H2C 109.5 . . ? H2B B2 H2C 109.5 . . ? O1 C1O H1O1 109.5 . . ? O1 C1O H1O2 109.5 . . ? H1O1 C1O H1O2 109.5 . . ? O1 C1O H1O3 109.5 . . ? H1O1 C1O H1O3 109.5 . . ? H1O2 C1O H1O3 109.5 . . ? C11 C1 P1 110.21(16) . . ? C11 C1 H1D 109.6 . . ? P1 C1 H1D 109.6 . . ? C11 C1 H1E 109.6 . . ? P1 C1 H1E 109.6 . . ? H1D C1 H1E 108.1 . . ? O2 C2O H2O1 109.5 . . ? O2 C2O H2O2 109.5 . . ? H2O1 C2O H2O2 109.5 . . ? O2 C2O H2O3 109.5 . . ? H2O1 C2O H2O3 109.5 . . ? H2O2 C2O H2O3 109.5 . . ? C41 C2 P2 109.76(17) . . ? C41 C2 H2D 109.7 . . ? P2 C2 H2D 109.7 . . ? C41 C2 H2E 109.7 . . ? P2 C2 H2E 109.7 . . ? H2D C2 H2E 108.2 . . ? C16 C11 C12 120.6(2) . . ? C16 C11 C1 118.6(2) . . ? C12 C11 C1 120.7(2) . . ? C11 C12 C13 117.25(19) . . ? C11 C12 C21 120.8(2) . . ? C13 C12 C21 121.92(19) . . ? O1 C13 C14 122.3(2) . . ? O1 C13 C12 117.06(19) . . ? C14 C13 C12 120.6(2) . . ? C15 C14 C13 120.4(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.3(2) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C15 C16 C11 120.7(2) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C26 C21 C22 117.00(19) . . ? C26 C21 C12 122.45(19) . . ? C22 C21 C12 120.52(18) . . ? C23 C22 C21 120.85(19) . . ? C23 C22 P1 120.02(17) . . ? C21 C22 P1 118.99(15) . . ? C24 C23 C22 120.4(2) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C25 C24 C23 119.6(2) . . ? C25 C24 H24 120.2 . . ? C23 C24 H24 120.2 . . ? C24 C25 C26 121.1(2) . . ? C24 C25 H25 119.4 . . ? C26 C25 H25 119.4 . . ? C25 C26 C21 121.0(2) . . ? C25 C26 H26 119.5 . . ? C21 C26 H26 119.5 . . ? C32 C31 C36 118.7(2) . . ? C32 C31 P1 119.60(18) . . ? C36 C31 P1 121.5(2) . . ? C31 C32 C33 121.4(3) . . ? C31 C32 H32 119.3 . . ? C33 C32 H32 119.3 . . ? C34 C33 C32 119.6(4) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C33 C34 C35 120.1(3) . . ? C33 C34 H34 120.0 . . ? C35 C34 H34 120.0 . . ? C34 C35 C36 120.6(3) . . ? C34 C35 H35 119.7 . . ? C36 C35 H35 119.7 . . ? C35 C36 C31 119.6(3) . . ? C35 C36 H36 120.2 . . ? C31 C36 H36 120.2 . . ? C46 C41 C42 121.2(2) . . ? C46 C41 C2 118.6(2) . . ? C42 C41 C2 120.1(2) . . ? C43 C42 C41 117.4(2) . . ? C43 C42 C51 122.4(2) . . ? C41 C42 C51 120.2(2) . . ? O2 C43 C44 122.9(2) . . ? O2 C43 C42 116.7(2) . . ? C44 C43 C42 120.4(2) . . ? C45 C44 C43 120.6(3) . . ? C45 C44 H44 119.7 . . ? C43 C44 H44 119.7 . . ? C44 C45 C46 120.5(2) . . ? C44 C45 H45 119.8 . . ? C46 C45 H45 119.8 . . ? C45 C46 C41 119.9(3) . . ? C45 C46 H46 120.1 . . ? C41 C46 H46 120.1 . . ? C56 C51 C52 116.8(2) . . ? C56 C51 C42 122.13(19) . . ? C52 C51 C42 121.03(19) . . ? C53 C52 C51 121.2(2) . . ? C53 C52 P2 120.03(17) . . ? C51 C52 P2 118.53(16) . . ? C52 C53 C54 120.7(2) . . ? C52 C53 H53 119.7 . . ? C54 C53 H53 119.7 . . ? C55 C54 C53 118.7(2) . . ? C55 C54 H54 120.6 . . ? C53 C54 H54 120.6 . . ? C54 C55 C56 121.6(2) . . ? C54 C55 H55 119.2 . . ? C56 C55 H55 119.2 . . ? C55 C56 C51 121.0(2) . . ? C55 C56 H56 119.5 . . ? C51 C56 H56 119.5 . . ? C66 C61 C62 118.9(3) . . ? C66 C61 P2 120.0(2) . . ? C62 C61 P2 120.7(2) . . ? C63 C62 C61 120.2(3) . . ? C63 C62 H62 119.9 . . ? C61 C62 H62 119.9 . . ? C64 C63 C62 120.5(3) . . ? C64 C63 H63 119.8 . . ? C62 C63 H63 119.8 . . ? C63 C64 C65 120.8(3) . . ? C63 C64 H64 119.6 . . ? C65 C64 H64 119.6 . . ? C64 C65 C66 118.9(4) . . ? C64 C65 H65 120.5 . . ? C66 C65 H65 120.5 . . ? C61 C66 C65 120.5(3) . . ? C61 C66 H66 119.7 . . ? C65 C66 H66 119.7 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.154 _refine_diff_density_min -0.218 _refine_diff_density_rms 0.039 #===END data_7 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H25 O3 P' _chemical_formula_weight 440.45 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 tetragonal _symmetry_space_group_name_H-M 'P 43 21 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, -z+1/4' '-x+1/2, y+1/2, -z+3/4' '-y, -x, -z+1/2' 'y, x, -z' 'y+1/2, -x+1/2, z+1/4' '-y+1/2, x+1/2, z+3/4' _cell_length_a 11.77150(10) _cell_length_b 11.77150(10) _cell_length_c 33.0827(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4584.21(9) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9796 _exptl_absorpt_correction_T_max 0.9854 _exptl_absorpt_process_details '(CrysAlis PRO; Agilent, 2011)' _exptl_special_details ; Absorption correction: CryAllisPro, Agilent Technologies, Empirical absorption correction using spherical harmonics, implemented in SCALE# ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Agilent Supernova Dual/Cu at zero/Atlas' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10.4933 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 32101 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0281 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -45 _diffrn_reflns_limit_l_max 45 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 30.30 _reflns_number_total 6415 _reflns_number_gt 5838 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0445P)^2^+1.4542P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.07(8) _refine_ls_number_reflns 6415 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0463 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.0985 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 0.70134(3) 0.06318(3) 0.528491(11) 0.01962(9) Uani 1 1 d . . . O1 O 0.90981(12) -0.05680(11) 0.39653(4) 0.0315(3) Uani 1 1 d . . . O2 O 0.33566(11) -0.02193(11) 0.44864(5) 0.0385(3) Uani 1 1 d . . . O3 O 0.80511(10) 0.03824(10) 0.55274(3) 0.0284(3) Uani 1 1 d . . . C1 C 0.84203(14) 0.03188(14) 0.41364(5) 0.0233(3) Uani 1 1 d . . . C2 C 0.80482(14) 0.00044(13) 0.45661(5) 0.0226(3) Uani 1 1 d . . . C2O C 0.2262(2) 0.0101(3) 0.43660(14) 0.0989(15) Uani 1 1 d . . . H2O1 H 0.2114 0.0865 0.4453 0.148 Uiso 1 1 calc R . . H2O2 H 0.1715 -0.0403 0.4485 0.148 Uiso 1 1 calc R . . H2O3 H 0.2206 0.0060 0.4077 0.148 Uiso 1 1 calc R . . C3 C 0.72851(13) 0.09332(13) 0.47563(4) 0.0206(3) Uani 1 1 d . . . C11 C 0.90205(14) 0.14599(14) 0.41169(5) 0.0230(3) Uani 1 1 d . . . C12 C 0.98907(16) 0.17316(17) 0.43837(6) 0.0330(4) Uani 1 1 d . . . H12 H 1.0117 0.1203 0.4577 0.040 Uiso 1 1 calc R . . C13 C 1.04263(19) 0.27788(19) 0.43665(6) 0.0424(5) Uani 1 1 d . . . H13 H 1.1009 0.2945 0.4547 0.051 Uiso 1 1 calc R . . C14 C 1.00993(18) 0.35775(18) 0.40830(6) 0.0402(4) Uani 1 1 d . . . H14 H 1.0462 0.4279 0.4072 0.048 Uiso 1 1 calc R . . C15 C 0.92311(17) 0.33283(16) 0.38172(6) 0.0348(4) Uani 1 1 d . . . H15 H 0.9004 0.3863 0.3627 0.042 Uiso 1 1 calc R . . C16 C 0.86945(15) 0.22739(15) 0.38351(5) 0.0273(3) Uani 1 1 d . . . H16 H 0.8109 0.2112 0.3655 0.033 Uiso 1 1 calc R . . C21 C 0.62731(14) 0.18705(13) 0.54756(4) 0.0220(3) Uani 1 1 d . . . C22 C 0.51802(15) 0.21788(16) 0.53608(5) 0.0309(4) Uani 1 1 d . . . H22 H 0.4773 0.1715 0.5185 0.037 Uiso 1 1 calc R . . C23 C 0.46882(17) 0.31732(17) 0.55052(6) 0.0374(4) Uani 1 1 d . . . H23 H 0.3957 0.3374 0.5426 0.045 Uiso 1 1 calc R . . C24 C 0.52900(18) 0.38648(16) 0.57680(6) 0.0376(4) Uani 1 1 d . . . H24 H 0.4965 0.4531 0.5865 0.045 Uiso 1 1 calc R . . C25 C 0.63676(18) 0.35631(17) 0.58845(6) 0.0364(5) Uani 1 1 d . . . H25 H 0.6768 0.4029 0.6061 0.044 Uiso 1 1 calc R . . C26 C 0.68694(16) 0.25753(15) 0.57431(5) 0.0283(4) Uani 1 1 d . . . H26 H 0.7599 0.2381 0.5825 0.034 Uiso 1 1 calc R . . C31 C 0.61621(13) 0.10741(13) 0.45400(4) 0.0203(3) Uani 1 1 d . . . C32 C 0.52747(14) 0.02878(13) 0.45995(4) 0.0203(3) Uani 1 1 d . . . C33 C 0.42341(15) 0.05011(14) 0.44010(5) 0.0268(3) Uani 1 1 d . . . C34 C 0.41066(16) 0.14232(16) 0.41422(6) 0.0332(4) Uani 1 1 d . . . H34 H 0.3423 0.1538 0.4008 0.040 Uiso 1 1 calc R . . C35 C 0.49990(17) 0.21688(16) 0.40858(5) 0.0323(4) Uani 1 1 d . . . H35 H 0.4914 0.2782 0.3911 0.039 Uiso 1 1 calc R . . C36 C 0.60127(14) 0.20126(14) 0.42855(5) 0.0264(3) Uani 1 1 d . . . H36 H 0.6600 0.2532 0.4251 0.032 Uiso 1 1 calc R . . C41 C 0.60737(13) -0.05643(13) 0.52380(4) 0.0211(3) Uani 1 1 d . . . C42 C 0.61577(17) -0.14424(15) 0.55189(5) 0.0312(4) Uani 1 1 d . . . H42 H 0.6618 -0.1358 0.5746 0.037 Uiso 1 1 calc R . . C43 C 0.5557(2) -0.24412(16) 0.54611(6) 0.0421(5) Uani 1 1 d . . . H43 H 0.5579 -0.3011 0.5656 0.050 Uiso 1 1 calc R . . C44 C 0.49240(19) -0.25858(16) 0.51117(6) 0.0383(4) Uani 1 1 d . . . H44 H 0.4551 -0.3270 0.5065 0.046 Uiso 1 1 calc R . . C45 C 0.48431(16) -0.17144(14) 0.48306(5) 0.0292(4) Uani 1 1 d . . . H45 H 0.4413 -0.1823 0.4598 0.035 Uiso 1 1 calc R . . C46 C 0.53946(13) -0.06767(13) 0.48902(4) 0.0218(3) Uani 1 1 d . . . H1 H 0.7766(18) 0.0334(17) 0.3960(6) 0.027(5) Uiso 1 1 d . . . H2A H 0.8706(18) -0.0093(16) 0.4735(6) 0.027(5) Uiso 1 1 d . . . H2B H 0.7601(14) -0.0751(15) 0.4557(5) 0.013(4) Uiso 1 1 d . . . H3 H 0.7711(15) 0.1666(16) 0.4746(5) 0.021(4) Uiso 1 1 d . . . H1O H 0.946(2) -0.089(2) 0.4160(8) 0.054(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.02077(19) 0.01907(19) 0.01902(16) -0.00213(14) 0.00097(15) -0.00149(15) O1 0.0387(7) 0.0314(7) 0.0245(6) -0.0025(5) 0.0076(5) 0.0122(6) O2 0.0264(7) 0.0300(7) 0.0589(8) 0.0089(6) -0.0136(6) -0.0052(5) O3 0.0265(6) 0.0307(6) 0.0280(5) -0.0007(5) -0.0045(5) -0.0020(5) C1 0.0229(8) 0.0258(8) 0.0212(7) -0.0016(6) 0.0042(6) 0.0041(6) C2 0.0231(8) 0.0225(8) 0.0221(7) 0.0000(6) 0.0054(6) 0.0053(6) C2O 0.0330(13) 0.0510(16) 0.213(4) 0.057(2) -0.0456(19) -0.0133(11) C3 0.0202(7) 0.0198(7) 0.0217(6) -0.0002(6) 0.0055(6) -0.0005(5) C11 0.0207(8) 0.0271(8) 0.0213(7) -0.0023(6) 0.0060(6) 0.0027(6) C12 0.0288(9) 0.0384(11) 0.0317(9) 0.0028(7) -0.0016(7) -0.0023(7) C13 0.0372(11) 0.0470(12) 0.0430(10) -0.0030(9) -0.0051(9) -0.0115(9) C14 0.0413(12) 0.0296(10) 0.0497(11) -0.0043(8) 0.0079(9) -0.0077(8) C15 0.0382(10) 0.0270(9) 0.0391(9) 0.0024(7) 0.0084(8) 0.0052(7) C16 0.0261(9) 0.0296(9) 0.0263(7) 0.0005(7) 0.0040(6) 0.0044(6) C21 0.0266(8) 0.0194(7) 0.0201(6) -0.0025(6) 0.0064(6) -0.0050(6) C22 0.0283(9) 0.0312(9) 0.0334(9) -0.0117(7) 0.0034(7) -0.0006(7) C23 0.0349(10) 0.0364(11) 0.0409(10) -0.0097(8) 0.0063(8) 0.0076(8) C24 0.0480(12) 0.0244(9) 0.0406(10) -0.0101(8) 0.0169(9) -0.0017(8) C25 0.0443(11) 0.0312(10) 0.0338(9) -0.0155(8) 0.0133(8) -0.0155(8) C26 0.0310(9) 0.0296(9) 0.0242(7) -0.0066(7) 0.0045(7) -0.0092(7) C31 0.0235(7) 0.0202(7) 0.0172(6) -0.0012(6) 0.0038(6) 0.0033(6) C32 0.0254(8) 0.0173(7) 0.0184(6) -0.0013(5) -0.0003(6) 0.0014(6) C33 0.0265(8) 0.0222(8) 0.0318(8) -0.0001(6) -0.0041(7) -0.0008(6) C34 0.0321(10) 0.0324(9) 0.0352(9) 0.0052(7) -0.0080(7) 0.0050(8) C35 0.0400(10) 0.0279(9) 0.0291(8) 0.0099(7) 0.0024(7) 0.0067(7) C36 0.0287(8) 0.0228(8) 0.0276(7) 0.0040(6) 0.0087(6) 0.0025(6) C41 0.0248(7) 0.0180(7) 0.0207(7) -0.0012(6) 0.0009(6) -0.0016(6) C42 0.0428(10) 0.0262(9) 0.0246(7) 0.0030(7) -0.0079(7) -0.0063(7) C43 0.0639(14) 0.0262(9) 0.0360(9) 0.0119(8) -0.0143(10) -0.0130(9) C44 0.0518(12) 0.0217(9) 0.0412(10) 0.0040(8) -0.0127(9) -0.0127(8) C45 0.0348(9) 0.0208(8) 0.0321(8) -0.0004(6) -0.0089(7) -0.0036(6) C46 0.0256(8) 0.0182(7) 0.0217(7) -0.0003(6) -0.0010(6) -0.0011(6) _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 1.4905(13) . ? P1 C41 1.7972(16) . ? P1 C21 1.8121(16) . ? P1 C3 1.8128(15) . ? O1 C1 1.4306(19) . ? O1 H1O 0.86(3) . ? O2 C33 1.366(2) . ? O2 C2O 1.401(3) . ? C1 C11 1.519(2) . ? C1 C2 1.533(2) . ? C1 H1 0.97(2) . ? C2 C3 1.549(2) . ? C2 H2A 0.96(2) . ? C2 H2B 1.034(17) . ? C2O H2O1 0.9600 . ? C2O H2O2 0.9600 . ? C2O H2O3 0.9600 . ? C3 C31 1.512(2) . ? C3 H3 0.998(19) . ? C11 C12 1.389(2) . ? C11 C16 1.391(2) . ? C12 C13 1.386(3) . ? C12 H12 0.9300 . ? C13 C14 1.383(3) . ? C13 H13 0.9300 . ? C14 C15 1.380(3) . ? C14 H14 0.9300 . ? C15 C16 1.394(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C22 1.390(2) . ? C21 C26 1.401(2) . ? C22 C23 1.391(2) . ? C22 H22 0.9300 . ? C23 C24 1.386(3) . ? C23 H23 0.9300 . ? C24 C25 1.372(3) . ? C24 H24 0.9300 . ? C25 C26 1.386(3) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C31 C36 1.400(2) . ? C31 C32 1.410(2) . ? C32 C33 1.412(2) . ? C32 C46 1.495(2) . ? C33 C34 1.391(2) . ? C34 C35 1.382(3) . ? C34 H34 0.9300 . ? C35 C36 1.376(3) . ? C35 H35 0.9300 . ? C36 H36 0.9300 . ? C41 C42 1.393(2) . ? C41 C46 1.407(2) . ? C42 C43 1.385(3) . ? C42 H42 0.9300 . ? C43 C44 1.386(3) . ? C43 H43 0.9300 . ? C44 C45 1.388(2) . ? C44 H44 0.9300 . ? C45 C46 1.397(2) . ? C45 H45 0.9300 . ? 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 C41 113.37(7) . . ? O3 P1 C21 111.42(7) . . ? C41 P1 C21 111.37(7) . . ? O3 P1 C3 114.40(7) . . ? C41 P1 C3 100.29(7) . . ? C21 P1 C3 105.26(7) . . ? C1 O1 H1O 107.3(17) . . ? C33 O2 C2O 118.02(16) . . ? O1 C1 C11 111.66(13) . . ? O1 C1 C2 110.49(13) . . ? C11 C1 C2 112.68(13) . . ? O1 C1 H1 102.7(12) . . ? C11 C1 H1 109.2(12) . . ? C2 C1 H1 109.6(12) . . ? C1 C2 C3 111.85(13) . . ? C1 C2 H2A 109.7(12) . . ? C3 C2 H2A 108.4(12) . . ? C1 C2 H2B 109.1(9) . . ? C3 C2 H2B 108.8(9) . . ? H2A C2 H2B 108.9(15) . . ? O2 C2O H2O1 109.5 . . ? O2 C2O H2O2 109.5 . . ? H2O1 C2O H2O2 109.5 . . ? O2 C2O H2O3 109.5 . . ? H2O1 C2O H2O3 109.5 . . ? H2O2 C2O H2O3 109.5 . . ? C31 C3 C2 113.08(13) . . ? C31 C3 P1 108.89(10) . . ? C2 C3 P1 110.86(11) . . ? C31 C3 H3 109.1(11) . . ? C2 C3 H3 107.8(11) . . ? P1 C3 H3 106.9(10) . . ? C12 C11 C16 118.08(17) . . ? C12 C11 C1 121.30(16) . . ? C16 C11 C1 120.61(15) . . ? C13 C12 C11 120.94(18) . . ? C13 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? C14 C13 C12 120.40(19) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C15 C14 C13 119.60(18) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C14 C15 C16 119.87(18) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C11 C16 C15 121.11(17) . . ? C11 C16 H16 119.4 . . ? C15 C16 H16 119.4 . . ? C22 C21 C26 118.79(15) . . ? C22 C21 P1 124.07(12) . . ? C26 C21 P1 117.08(13) . . ? C21 C22 C23 120.77(17) . . ? C21 C22 H22 119.6 . . ? C23 C22 H22 119.6 . . ? C24 C23 C22 119.80(19) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C25 C24 C23 119.77(18) . . ? C25 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C24 C25 C26 121.10(17) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C25 C26 C21 119.76(17) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? C36 C31 C32 120.60(15) . . ? C36 C31 C3 118.74(14) . . ? C32 C31 C3 120.65(14) . . ? C31 C32 C33 117.46(14) . . ? C31 C32 C46 121.25(14) . . ? C33 C32 C46 121.07(14) . . ? O2 C33 C34 122.03(16) . . ? O2 C33 C32 116.70(14) . . ? C34 C33 C32 121.24(16) . . ? C35 C34 C33 119.80(17) . . ? C35 C34 H34 120.1 . . ? C33 C34 H34 120.1 . . ? C36 C35 C34 120.63(16) . . ? C36 C35 H35 119.7 . . ? C34 C35 H35 119.7 . . ? C35 C36 C31 120.19(16) . . ? C35 C36 H36 119.9 . . ? C31 C36 H36 119.9 . . ? C42 C41 C46 121.05(14) . . ? C42 C41 P1 118.68(12) . . ? C46 C41 P1 119.60(12) . . ? C43 C42 C41 120.08(16) . . ? C43 C42 H42 120.0 . . ? C41 C42 H42 120.0 . . ? C42 C43 C44 119.60(17) . . ? C42 C43 H43 120.2 . . ? C44 C43 H43 120.2 . . ? C43 C44 C45 120.33(17) . . ? C43 C44 H44 119.8 . . ? C45 C44 H44 119.8 . . ? C44 C45 C46 121.31(15) . . ? C44 C45 H45 119.3 . . ? C46 C45 H45 119.3 . . ? C45 C46 C41 117.49(14) . . ? C45 C46 C32 121.96(14) . . ? C41 C46 C32 120.55(14) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 30.30 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.371 _refine_diff_density_min -0.339 _refine_diff_density_rms 0.043 #===END data_8d _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H22 B O3 P' _chemical_formula_weight 364.17 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 8.93335(14) _cell_length_b 14.7790(2) _cell_length_c 14.9251(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1970.50(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.228 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.156 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9876 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details '(CrysAlis PRO; Agilent, 2011)' _exptl_special_details ; Absorption correction: CryAllisPro, Agilent Technologies, Empirical absorption correction using spherical harmonics, implemented in SCALE# ABSPACK scaling algorithm. ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Agilent Supernova Dual/Cu at zero/Atlas' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean 10.4933 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 40296 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 30.37 _reflns_number_total 5643 _reflns_number_gt 4411 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2\s(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^)+(0.0410P)^2^+0.2580P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.02(8) _refine_ls_number_reflns 5643 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0987 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.22572(5) 0.66171(3) 0.15600(3) 0.03816(11) Uani 1 1 d . . . B1 B 0.3088(3) 0.77564(14) 0.12986(18) 0.0556(6) Uani 1 1 d . . . H1A H 0.3052 0.8131 0.1824 0.083 Uiso 1 1 calc R . . H1B H 0.2526 0.8037 0.0826 0.083 Uiso 1 1 calc R . . H1C H 0.4109 0.7683 0.1113 0.083 Uiso 1 1 calc R . . O2 O 0.55651(17) 0.51606(9) 0.06361(10) 0.0615(4) Uani 1 1 d . . . O4 O 0.3425(2) 0.23004(9) 0.00500(12) 0.0775(5) Uani 1 1 d . . . O6 O 0.07569(16) 0.45098(8) 0.16709(10) 0.0553(3) Uani 1 1 d . . . C C 0.2551(2) 0.57460(11) 0.07048(11) 0.0436(4) Uani 1 1 d . . . C11 C 0.02822(19) 0.66749(12) 0.18233(11) 0.0436(4) Uani 1 1 d . . . C12 C -0.0635(3) 0.71330(18) 0.12303(15) 0.0653(6) Uani 1 1 d . . . H12 H -0.0234 0.7391 0.0715 0.078 Uiso 1 1 calc R . . C13 C -0.2155(3) 0.7206(2) 0.14065(18) 0.0834(8) Uani 1 1 d . . . H13 H -0.2773 0.7510 0.1005 0.100 Uiso 1 1 calc R . . C14 C -0.2749(3) 0.68370(18) 0.21624(17) 0.0733(7) Uani 1 1 d . . . H14 H -0.3768 0.6890 0.2276 0.088 Uiso 1 1 calc R . . C15 C -0.1853(2) 0.63907(17) 0.27509(17) 0.0687(6) Uani 1 1 d . . . H15 H -0.2264 0.6140 0.3267 0.082 Uiso 1 1 calc R . . C16 C -0.0330(2) 0.63064(14) 0.25882(14) 0.0555(5) Uani 1 1 d . . . H16 H 0.0277 0.6002 0.2995 0.067 Uiso 1 1 calc R . . C21 C 0.3157(2) 0.48701(11) 0.11667(11) 0.0388(4) Uani 1 1 d . . . C22 C 0.4505(2) 0.45231(12) 0.06631(11) 0.0446(4) Uani 1 1 d . . . C23 C 0.4592(2) 0.36864(13) 0.03154(13) 0.0518(5) Uani 1 1 d . . . H23 H 0.5459 0.3510 0.0018 0.062 Uiso 1 1 calc R . . C24 C 0.3363(3) 0.30558(12) 0.03955(13) 0.0525(5) Uani 1 1 d . . . C25 C 0.2047(2) 0.33364(12) 0.08844(12) 0.0477(4) Uani 1 1 d . . . H25 H 0.1262 0.2930 0.0962 0.057 Uiso 1 1 calc R . . C26 C 0.1936(2) 0.41690(11) 0.12268(11) 0.0416(4) Uani 1 1 d . . . C27 C 0.6916(3) 0.49748(18) 0.0148(2) 0.0846(8) Uani 1 1 d . . . H27A H 0.7329 0.4410 0.0346 0.127 Uiso 1 1 calc R . . H27B H 0.7626 0.5451 0.0252 0.127 Uiso 1 1 calc R . . H27C H 0.6695 0.4940 -0.0481 0.127 Uiso 1 1 calc R . . C28 C -0.0444(3) 0.39133(16) 0.19068(18) 0.0722(6) Uani 1 1 d . . . H28A H -0.0836 0.3635 0.1375 0.108 Uiso 1 1 calc R . . H28B H -0.1223 0.4251 0.2198 0.108 Uiso 1 1 calc R . . H28C H -0.0080 0.3454 0.2306 0.108 Uiso 1 1 calc R . . C31 C 0.36199(19) 0.51315(11) 0.21250(11) 0.0371(3) Uani 1 1 d . . . C32 C 0.4410(2) 0.45620(13) 0.26885(12) 0.0489(4) Uani 1 1 d . . . H32 H 0.4681 0.3985 0.2500 0.059 Uiso 1 1 calc R . . C33 C 0.4792(2) 0.48613(15) 0.35372(13) 0.0547(5) Uani 1 1 d . . . H33 H 0.5325 0.4483 0.3919 0.066 Uiso 1 1 calc R . . C34 C 0.4391(2) 0.57116(15) 0.38209(12) 0.0558(5) Uani 1 1 d . . . H34 H 0.4663 0.5904 0.4391 0.067 Uiso 1 1 calc R . . C35 C 0.3591(2) 0.62813(13) 0.32718(12) 0.0485(4) Uani 1 1 d . . . H35 H 0.3316 0.6855 0.3469 0.058 Uiso 1 1 calc R . . C36 C 0.31974(18) 0.59879(11) 0.24156(11) 0.0380(3) Uani 1 1 d . . . H1 H 0.329(2) 0.5973(13) 0.0284(14) 0.053(5) Uiso 1 1 d . . . H2 H 0.173(2) 0.5610(14) 0.0394(14) 0.058(6) 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 0.0398(2) 0.02970(17) 0.0449(2) -0.00389(17) 0.00409(18) -0.00024(17) B1 0.0523(13) 0.0386(10) 0.0760(15) 0.0013(10) 0.0073(11) -0.0056(9) O2 0.0598(8) 0.0485(7) 0.0763(9) -0.0162(7) 0.0273(8) -0.0066(7) O4 0.0986(13) 0.0406(7) 0.0934(12) -0.0284(8) -0.0022(10) 0.0053(8) O6 0.0521(8) 0.0427(7) 0.0712(9) -0.0087(6) 0.0116(7) -0.0067(6) C 0.0596(12) 0.0352(8) 0.0361(8) -0.0022(7) 0.0028(9) 0.0019(8) C11 0.0406(9) 0.0406(8) 0.0498(9) -0.0083(8) 0.0035(7) -0.0006(8) C12 0.0503(11) 0.0902(16) 0.0554(11) 0.0081(11) -0.0007(10) 0.0061(12) C13 0.0468(12) 0.124(2) 0.0798(16) 0.0104(15) -0.0112(12) 0.0133(15) C14 0.0388(10) 0.0970(19) 0.0840(15) -0.0119(14) 0.0074(11) -0.0047(12) C15 0.0532(12) 0.0771(15) 0.0758(14) 0.0007(12) 0.0176(11) -0.0088(11) C16 0.0494(11) 0.0534(11) 0.0637(12) 0.0062(9) 0.0109(9) 0.0029(9) C21 0.0504(10) 0.0306(7) 0.0355(7) -0.0052(6) 0.0023(7) 0.0002(7) C22 0.0533(10) 0.0385(9) 0.0420(9) -0.0044(7) 0.0050(8) 0.0024(8) C23 0.0617(11) 0.0428(9) 0.0511(10) -0.0116(8) 0.0049(9) 0.0097(9) C24 0.0720(13) 0.0355(8) 0.0499(10) -0.0088(8) -0.0087(10) 0.0076(9) C25 0.0583(11) 0.0345(8) 0.0504(9) -0.0025(7) -0.0102(8) -0.0062(9) C26 0.0488(10) 0.0354(8) 0.0405(8) -0.0015(7) -0.0043(7) -0.0007(7) C27 0.0731(16) 0.0687(15) 0.112(2) -0.0121(14) 0.0474(15) -0.0012(13) C28 0.0633(13) 0.0647(14) 0.0885(16) -0.0007(12) 0.0109(13) -0.0156(12) C31 0.0385(8) 0.0342(8) 0.0385(8) -0.0043(6) 0.0018(7) -0.0013(7) C32 0.0548(11) 0.0438(10) 0.0482(10) -0.0015(8) -0.0009(9) 0.0050(9) C33 0.0563(11) 0.0615(11) 0.0464(10) 0.0052(9) -0.0056(9) 0.0053(9) C34 0.0553(12) 0.0754(13) 0.0368(9) -0.0087(9) -0.0004(8) -0.0055(11) C35 0.0462(9) 0.0511(10) 0.0482(10) -0.0159(8) 0.0062(8) -0.0006(8) C36 0.0355(8) 0.0380(8) 0.0404(8) -0.0048(7) 0.0044(7) -0.0022(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C36 1.7892(17) . ? P1 C11 1.8095(17) . ? P1 C 1.8318(17) . ? P1 B1 1.881(2) . ? B1 H1A 0.9600 . ? B1 H1B 0.9600 . ? B1 H1C 0.9600 . ? O2 C22 1.337(2) . ? O2 C27 1.436(2) . ? O4 C24 1.231(2) . ? O6 C26 1.343(2) . ? O6 C28 1.433(2) . ? C C21 1.563(2) . ? C H1 0.97(2) . ? C H2 0.89(2) . ? C11 C16 1.378(3) . ? C11 C12 1.383(3) . ? C12 C13 1.387(3) . ? C12 H12 0.9300 . ? C13 C14 1.361(4) . ? C13 H13 0.9300 . ? C14 C15 1.359(3) . ? C14 H14 0.9300 . ? C15 C16 1.388(3) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C21 C26 1.507(2) . ? C21 C22 1.509(2) . ? C21 C31 1.538(2) . ? C22 C23 1.343(2) . ? C23 C24 1.445(3) . ? C23 H23 0.9300 . ? C24 C25 1.445(3) . ? C25 C26 1.336(2) . ? C25 H25 0.9300 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C31 C32 1.383(3) . ? C31 C36 1.390(2) . ? C32 C33 1.384(3) . ? C32 H32 0.9300 . ? C33 C34 1.374(3) . ? C33 H33 0.9300 . ? C34 C35 1.375(3) . ? C34 H34 0.9300 . ? C35 C36 1.394(2) . ? C35 H35 0.9300 . ? 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 C36 P1 C11 109.10(8) . . ? C36 P1 C 93.71(8) . . ? C11 P1 C 108.93(9) . . ? C36 P1 B1 115.34(10) . . ? C11 P1 B1 112.80(10) . . ? C P1 B1 115.34(10) . . ? P1 B1 H1A 109.5 . . ? P1 B1 H1B 109.5 . . ? H1A B1 H1B 109.5 . . ? P1 B1 H1C 109.5 . . ? H1A B1 H1C 109.5 . . ? H1B B1 H1C 109.5 . . ? C22 O2 C27 118.43(16) . . ? C26 O6 C28 118.57(15) . . ? C21 C P1 108.93(11) . . ? C21 C H1 109.7(12) . . ? P1 C H1 107.8(12) . . ? C21 C H2 109.1(14) . . ? P1 C H2 113.8(14) . . ? H1 C H2 107.4(18) . . ? C16 C11 C12 119.24(18) . . ? C16 C11 P1 123.24(15) . . ? C12 C11 P1 117.50(15) . . ? C11 C12 C13 119.8(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C15 C14 C13 120.1(2) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 120.5(2) . . ? C14 C15 H15 119.7 . . ? C16 C15 H15 119.7 . . ? C11 C16 C15 119.9(2) . . ? C11 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C26 C21 C22 111.92(14) . . ? C26 C21 C31 108.18(13) . . ? C22 C21 C31 109.51(14) . . ? C26 C21 C 110.19(15) . . ? C22 C21 C 109.74(14) . . ? C31 C21 C 107.16(13) . . ? O2 C22 C23 126.57(18) . . ? O2 C22 C21 109.94(14) . . ? C23 C22 C21 123.48(18) . . ? C22 C23 C24 121.17(18) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? O4 C24 C25 120.6(2) . . ? O4 C24 C23 121.1(2) . . ? C25 C24 C23 118.36(15) . . ? C26 C25 C24 121.17(18) . . ? C26 C25 H25 119.4 . . ? C24 C25 H25 119.4 . . ? C25 C26 O6 126.32(17) . . ? C25 C26 C21 123.85(17) . . ? O6 C26 C21 109.83(13) . . ? O2 C27 H27A 109.5 . . ? O2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O6 C28 H28A 109.5 . . ? O6 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O6 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C32 C31 C36 120.18(15) . . ? C32 C31 C21 123.34(15) . . ? C36 C31 C21 116.48(15) . . ? C31 C32 C33 119.18(18) . . ? C31 C32 H32 120.4 . . ? C33 C32 H32 120.4 . . ? C34 C33 C32 120.67(19) . . ? C34 C33 H33 119.7 . . ? C32 C33 H33 119.7 . . ? C33 C34 C35 120.79(17) . . ? C33 C34 H34 119.6 . . ? C35 C34 H34 119.6 . . ? C34 C35 C36 119.12(17) . . ? C34 C35 H35 120.4 . . ? C36 C35 H35 120.4 . . ? C31 C36 C35 120.04(16) . . ? C31 C36 P1 112.20(12) . . ? C35 C36 P1 127.65(14) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 30.37 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.217 _refine_diff_density_min -0.180 _refine_diff_density_rms 0.034 #===END