Supplementary Material (ESI) for Perkin Transactions This journal is © The Royal Society of Chemistry 2002 data_sw9804 _database_code_CSD 112685 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Warren, Stuart' 'Feeder, Neil' 'Fox, David J.' 'Medlock, Jonathan A.' _publ_contact_author_name 'Dr Stuart Warren' _publ_contact_author_address ; University Chemical Laboratory Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email 'SW134@CAM.AC.UK' _publ_section_title ; Synthesis, X-ray crystal structures and Horner-Wittig addition reactions of some protected beta-aminophosphine oxides ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 N O3 P' _chemical_formula_weight 455.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.2955 0.4335 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.759(6) _cell_length_b 10.339(6) _cell_length_c 22.581(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.56(4) _cell_angle_gamma 90.00 _cell_volume 2442(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 30 _cell_measurement_theta_max 50 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 1.228 _exptl_absorpt_correction_type 'Psi-Scans' _exptl_absorpt_correction_T_min 0.7095 _exptl_absorpt_correction_T_max 0.8666 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Stoe II' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 90 _diffrn_standards_decay_% 0.1 _diffrn_reflns_number 6545 _diffrn_reflns_av_R_equivalents 0.0310 _diffrn_reflns_av_sigmaI/netI 0.0979 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 4.03 _diffrn_reflns_theta_max 55.06 _reflns_number_total 6122 _reflns_number_gt 4012 _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 w=1/[\s^2^(Fo^2^)+(0.0749P)^2^+1.0660P] 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 0.01(4) _refine_ls_number_reflns 6122 _refine_ls_number_parameters 538 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1188 _refine_ls_R_factor_gt 0.0619 _refine_ls_wR_factor_ref 0.1543 _refine_ls_wR_factor_gt 0.1308 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.083 _refine_ls_shift/su_mean 0.008 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group P1_1 P -0.10131(16) 0.8864(2) 0.40471(7) 0.0278(4) Uani 1 d . . . O1_1 O -0.1149(4) 1.0229(4) 0.42409(19) 0.0288(11) Uani 1 d . . . O2_1 O 0.0106(5) 0.9680(5) 0.6302(2) 0.0549(14) Uani 1 d . . . O3_1 O -0.5570(4) 0.6228(5) 0.5321(3) 0.0597(15) Uani 1 d . . . N1_1 N 0.0347(5) 0.7852(6) 0.5806(2) 0.0303(13) Uani 1 d . . . H1_1 H 0.0745 0.7107 0.5813 0.036 Uiso 1 calc R . . C1_1 C -0.0014(5) 0.8743(7) 0.3513(3) 0.0273(15) Uani 1 d . . . C2_1 C 0.0629(6) 0.7621(6) 0.3427(3) 0.0389(18) Uani 1 d . . . H2_1 H 0.0542 0.6871 0.3658 0.047 Uiso 1 calc R . . C3_1 C 0.1399(7) 0.7573(8) 0.3012(3) 0.048(2) Uani 1 d . . . H3_1 H 0.1852 0.6806 0.2965 0.058 Uiso 1 calc R . . C4_1 C 0.1495(7) 0.8663(8) 0.2666(3) 0.0445(19) Uani 1 d . . . H4_1 H 0.2004 0.8644 0.2375 0.053 Uiso 1 calc R . . C5_1 C 0.0859(7) 0.9750(8) 0.2747(3) 0.0436(19) Uani 1 d . . . H5_1 H 0.0949 1.0496 0.2515 0.052 Uiso 1 calc R . . C6_1 C 0.0083(6) 0.9820(7) 0.3154(3) 0.0374(17) Uani 1 d . . . H6_1 H -0.0377 1.0589 0.3189 0.045 Uiso 1 calc R . . C7_1 C -0.2529(6) 0.8152(7) 0.3700(3) 0.0258(16) Uani 1 d . . . C8_1 C -0.2687(7) 0.6847(7) 0.3533(3) 0.0364(19) Uani 1 d . . . H8_1 H -0.1970 0.6283 0.3605 0.044 Uiso 1 calc R . . C9_1 C -0.3862(7) 0.6395(8) 0.3267(3) 0.044(2) Uani 1 d . . . H9_1 H -0.3960 0.5505 0.3162 0.053 Uiso 1 calc R . . C10_1 C -0.4934(7) 0.7189(8) 0.3144(3) 0.046(2) Uani 1 d . . . H10_1 H -0.5747 0.6848 0.2949 0.055 Uiso 1 calc R . . C11_1 C -0.4804(6) 0.8481(8) 0.3307(3) 0.045(2) Uani 1 d . . . H11_1 H -0.5529 0.9034 0.3228 0.053 Uiso 1 calc R . . C12_1 C -0.3615(6) 0.8958(7) 0.3583(3) 0.0351(17) Uani 1 d . . . H12_1 H -0.3525 0.9844 0.3696 0.042 Uiso 1 calc R . . C13_1 C -0.0224(6) 0.7869(7) 0.4689(3) 0.0303(15) Uani 1 d . . . H13A_1 H -0.0414 0.6948 0.4587 0.036 Uiso 1 calc R . . H13B_1 H 0.0712 0.7990 0.4762 0.036 Uiso 1 calc R . . C14_1 C -0.0658(5) 0.8208(6) 0.5277(3) 0.0276(16) Uani 1 d . . . H14_1 H -0.0742 0.9171 0.5285 0.033 Uiso 1 calc R . . C15_1 C -0.1953(6) 0.7657(7) 0.5288(3) 0.0294(16) Uani 1 d . . . C16_1 C -0.3030(6) 0.8411(6) 0.5078(3) 0.0337(18) Uani 1 d . . . H16_1 H -0.2916 0.9263 0.4942 0.040 Uiso 1 calc R . . C17_1 C -0.4268(6) 0.7993(7) 0.5055(3) 0.0332(16) Uani 1 d . . . H17_1 H -0.4989 0.8525 0.4898 0.040 Uiso 1 calc R . . C18_1 C -0.4399(5) 0.6722(7) 0.5281(3) 0.0367(18) Uani 1 d . . . C19_1 C -0.3324(6) 0.5973(7) 0.5511(3) 0.046(2) Uani 1 d . . . H19_1 H -0.3418 0.5141 0.5674 0.055 Uiso 1 calc R . . C20_1 C -0.2133(6) 0.6422(7) 0.5506(3) 0.0408(18) Uani 1 d . . . H20_1 H -0.1412 0.5884 0.5655 0.049 Uiso 1 calc R . . C21_1 C -0.6665(6) 0.6983(8) 0.5063(4) 0.067(3) Uani 1 d . . . H21A_1 H -0.7435 0.6532 0.5111 0.100 Uiso 1 calc R . . H21B_1 H -0.6712 0.7119 0.4628 0.100 Uiso 1 calc R . . H21C_1 H -0.6602 0.7822 0.5270 0.100 Uiso 1 calc R . . C22_1 C 0.0661(6) 0.8655(7) 0.6277(3) 0.0338(16) Uani 1 d . . . C23_1 C 0.1755(6) 0.8292(6) 0.6795(3) 0.0358(18) Uani 1 d . . . C24_1 C 0.1811(7) 0.8849(8) 0.7361(3) 0.053(2) Uani 1 d . . . H24_1 H 0.1149 0.9407 0.7420 0.064 Uiso 1 calc R . . C25_1 C 0.2841(9) 0.8577(9) 0.7836(3) 0.065(3) Uani 1 d . . . H25_1 H 0.2872 0.8944 0.8225 0.079 Uiso 1 calc R . . C26_1 C 0.3803(9) 0.7810(9) 0.7766(4) 0.069(3) Uani 1 d . . . H26_1 H 0.4497 0.7646 0.8104 0.083 Uiso 1 calc R . . C27_1 C 0.3796(7) 0.7256(8) 0.7206(4) 0.061(2) Uani 1 d . . . H27_1 H 0.4486 0.6730 0.7153 0.073 Uiso 1 calc R . . C28_1 C 0.2735(6) 0.7497(7) 0.6720(3) 0.0444(19) Uani 1 d . . . H28_1 H 0.2695 0.7106 0.6335 0.053 Uiso 1 calc R . . P1_2 P -0.02507(17) 0.7962(2) 0.06828(8) 0.0328(5) Uani 1 d . . . O1_2 O -0.0133(5) 0.6544(4) 0.0580(2) 0.0423(13) Uani 1 d . . . O2_2 O 0.1871(6) 0.7059(6) -0.0444(3) 0.085(2) Uani 1 d . . . O3_2 O -0.3466(5) 0.9482(6) -0.2914(2) 0.0578(15) Uani 1 d . . . N1_2 N 0.0828(5) 0.8960(6) -0.0472(2) 0.0328(14) Uani 1 d . . . H1_2 H 0.0894 0.9808 -0.0461 0.039 Uiso 1 calc R . . C1_2 C 0.1296(6) 0.8679(7) 0.1006(3) 0.0345(17) Uani 1 d . . . C2_2 C 0.1435(7) 0.9982(8) 0.1153(3) 0.0429(19) Uani 1 d . . . H2_2 H 0.0713 1.0539 0.1065 0.052 Uiso 1 calc R . . C3_2 C 0.2630(7) 1.0465(8) 0.1429(4) 0.046(2) Uani 1 d . . . H3_2 H 0.2723 1.1359 0.1526 0.055 Uiso 1 calc R . . C4_2 C 0.3679(7) 0.9675(9) 0.1563(3) 0.047(2) Uani 1 d . . . H4_2 H 0.4499 1.0013 0.1748 0.056 Uiso 1 calc R . . C5_2 C 0.3521(8) 0.8353(8) 0.1422(4) 0.052(2) Uani 1 d . . . H5_2 H 0.4236 0.7786 0.1517 0.062 Uiso 1 calc R . . C6_2 C 0.2340(7) 0.7883(8) 0.1147(3) 0.044(2) Uani 1 d . . . H6_2 H 0.2242 0.6988 0.1052 0.052 Uiso 1 calc R . . C7_2 C -0.1158(8) 0.8364(8) 0.1222(4) 0.032(4) Uiso 0.65 d PG A 1 C8_2 C -0.1840(9) 0.9511(7) 0.1204(4) 0.038(3) Uiso 0.65 d PG A 1 H8_2 H -0.1785 1.0155 0.0911 0.046 Uiso 0.65 calc PR A 1 C9_2 C -0.2603(8) 0.9715(7) 0.1614(4) 0.058(4) Uiso 0.65 d PG A 1 H9_2 H -0.3069 1.0498 0.1602 0.070 Uiso 0.65 calc PR A 1 C10_2 C -0.2683(8) 0.8772(10) 0.2042(4) 0.052(4) Uiso 0.65 d PG A 1 H10_2 H -0.3204 0.8911 0.2323 0.063 Uiso 0.65 calc PR A 1 C11_2 C -0.2001(8) 0.7625(8) 0.2060(3) 0.054(3) Uiso 0.65 d PG A 1 H11_2 H -0.2056 0.6981 0.2353 0.065 Uiso 0.65 calc PR A 1 C12_2 C -0.1238(8) 0.7421(7) 0.1650(4) 0.048(3) Uiso 0.65 d PG A 1 H12_2 H -0.0772 0.6638 0.1662 0.058 Uiso 0.65 calc PR A 1 C7'_2 C -0.1348(13) 0.8127(15) 0.1199(6) 0.028(7) Uiso 0.35 d PG A 2 C8'_2 C -0.1701(15) 0.9343(12) 0.1366(7) 0.054(8) Uiso 0.35 d PG A 2 H8'_2 H -0.1445 1.0097 0.1185 0.064 Uiso 0.35 calc PR A 2 C9'_2 C -0.2430(14) 0.9456(10) 0.1797(7) 0.025(5) Uiso 0.35 d PG A 2 H9'_2 H -0.2671 1.0287 0.1910 0.030 Uiso 0.35 calc PR A 2 C10'_2 C -0.2804(11) 0.8353(12) 0.2061(5) 0.021(5) Uiso 0.35 d PG A 2 H10'_2 H -0.3302 0.8431 0.2356 0.025 Uiso 0.35 calc PR A 2 C11'_2 C -0.2451(13) 0.7138(11) 0.1895(6) 0.046(6) Uiso 0.35 d PG A 2 H11'_2 H -0.2707 0.6384 0.2076 0.055 Uiso 0.35 calc PR A 2 C12'_2 C -0.1722(13) 0.7025(12) 0.1464(6) 0.034(5) Uiso 0.35 d PG A 2 H12'_2 H -0.1481 0.6194 0.1350 0.041 Uiso 0.35 calc PR A 2 C13_2 C -0.1012(6) 0.8783(7) -0.0009(3) 0.0291(15) Uani 1 d . . . H13A_2 H -0.1936 0.8573 -0.0113 0.035 Uiso 1 calc R . . H13B_2 H -0.0924 0.9729 0.0056 0.035 Uiso 1 calc R . . C14_2 C -0.0423(6) 0.8394(6) -0.0545(3) 0.0281(16) Uani 1 d . . . H14_2 H -0.0304 0.7435 -0.0523 0.034 Uiso 1 calc R . . C15_2 C -0.1260(6) 0.8699(7) -0.1180(3) 0.0292(16) Uani 1 d . . . C16_2 C -0.0813(6) 0.8349(7) -0.1680(3) 0.0399(19) Uani 1 d . . . H16_2 H -0.0003 0.7939 -0.1621 0.048 Uiso 1 calc R . . C17_2 C -0.1513(7) 0.8580(8) -0.2268(3) 0.048(2) Uani 1 d . . . H17_2 H -0.1189 0.8323 -0.2606 0.058 Uiso 1 calc R . . C18_2 C -0.2677(7) 0.9183(7) -0.2357(3) 0.045(2) Uani 1 d . . . C19_2 C -0.3136(7) 0.9554(8) -0.1861(3) 0.0436(19) Uani 1 d . . . H19_2 H -0.3939 0.9977 -0.1919 0.052 Uiso 1 calc R . . C20_2 C -0.2415(8) 0.9306(7) -0.1276(3) 0.047(2) Uani 1 d . . . H20_2 H -0.2734 0.9566 -0.0936 0.057 Uiso 1 calc R . . C21_2 C -0.3079(9) 0.9074(10) -0.3448(3) 0.079(3) Uani 1 d . . . H21A_2 H -0.3718 0.9350 -0.3810 0.119 Uiso 1 calc R . . H21B_2 H -0.3003 0.8130 -0.3447 0.119 Uiso 1 calc R . . H21C_2 H -0.2251 0.9464 -0.3452 0.119 Uiso 1 calc R . . C22_2 C 0.1889(7) 0.8262(7) -0.0419(3) 0.046(2) Uani 1 d D . . C23_2 C 0.3112(6) 0.8918(9) -0.0400(5) 0.074(11) Uiso 0.55 d PGD B 1 C24_2 C 0.3350(7) 1.0058(9) -0.0067(5) 0.060(4) Uiso 0.55 d PG B 1 H24_2 H 0.2676 1.0481 0.0063 0.073 Uiso 0.55 calc PR B 1 C25_2 C 0.4575(9) 1.0581(8) 0.0076(5) 0.082(5) Uiso 0.55 d PG B 1 H25_2 H 0.4738 1.1360 0.0304 0.098 Uiso 0.55 calc PR B 1 C26_2 C 0.5561(5) 0.9963(10) -0.0114(5) 0.036(3) Uiso 0.55 d PG B 1 H26_2 H 0.6398 1.0320 -0.0016 0.043 Uiso 0.55 calc PR B 1 C27_2 C 0.5323(6) 0.8822(9) -0.0447(4) 0.064(4) Uiso 0.55 d PG B 1 H27_2 H 0.5998 0.8399 -0.0576 0.077 Uiso 0.55 calc PR B 1 C28_2 C 0.4099(8) 0.8299(8) -0.0590(4) 0.051(4) Uiso 0.55 d PG B 1 H28_2 H 0.3936 0.7520 -0.0818 0.062 Uiso 0.55 calc PR B 1 C23'_2 C 0.3067(6) 0.9044(9) -0.0336(5) 0.016(6) Uiso 0.45 d PGD B 2 C24'_2 C 0.3029(8) 1.0210(9) -0.0646(5) 0.062(5) Uiso 0.45 d PG B 2 H24'_2 H 0.2242 1.0520 -0.0889 0.074 Uiso 0.45 calc PR B 2 C25'_2 C 0.4143(11) 1.0922(9) -0.0602(6) 0.096(8) Uiso 0.45 d PG B 2 H25'_2 H 0.4117 1.1719 -0.0814 0.115 Uiso 0.45 calc PR B 2 C26'_2 C 0.5294(8) 1.0469(12) -0.0247(6) 0.067(6) Uiso 0.45 d PG B 2 H26'_2 H 0.6056 1.0955 -0.0216 0.081 Uiso 0.45 calc PR B 2 C27'_2 C 0.5332(6) 0.9303(12) 0.0064(6) 0.068(6) Uiso 0.45 d PG B 2 H27'_2 H 0.6120 0.8993 0.0306 0.081 Uiso 0.45 calc PR B 2 C28'_2 C 0.4218(9) 0.8591(8) 0.0019(5) 0.051(5) Uiso 0.45 d PG B 2 H28'_2 H 0.4244 0.7794 0.0231 0.062 Uiso 0.45 calc PR B 2 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_1 0.0234(9) 0.0305(10) 0.0280(10) 0.0029(9) 0.0032(8) 0.0001(9) O1_1 0.032(3) 0.022(2) 0.031(2) 0.000(2) 0.005(2) 0.003(2) O2_1 0.061(3) 0.040(3) 0.056(3) -0.019(3) 0.000(3) 0.013(3) O3_1 0.035(3) 0.058(3) 0.086(4) 0.018(3) 0.013(3) -0.002(3) N1_1 0.035(3) 0.026(3) 0.029(3) -0.004(3) 0.004(3) 0.008(3) C1_1 0.017(3) 0.034(4) 0.029(3) -0.003(3) 0.002(3) -0.011(3) C2_1 0.043(4) 0.028(4) 0.052(5) 0.009(3) 0.023(4) 0.009(3) C3_1 0.043(5) 0.047(5) 0.059(5) 0.005(4) 0.019(4) 0.014(4) C4_1 0.041(4) 0.061(6) 0.035(4) 0.006(4) 0.016(3) 0.000(4) C5_1 0.054(5) 0.050(5) 0.028(4) 0.013(4) 0.011(4) -0.013(4) C6_1 0.045(4) 0.034(4) 0.033(4) 0.004(3) 0.008(4) 0.000(3) C7_1 0.019(3) 0.036(4) 0.021(3) 0.002(3) 0.002(3) 0.003(3) C8_1 0.040(5) 0.031(4) 0.039(4) -0.002(3) 0.013(4) -0.005(3) C9_1 0.036(5) 0.039(5) 0.055(5) -0.008(4) 0.008(4) -0.012(4) C10_1 0.029(4) 0.056(5) 0.049(5) -0.009(4) 0.001(4) -0.004(4) C11_1 0.025(4) 0.066(6) 0.037(4) 0.003(4) -0.005(3) -0.002(4) C12_1 0.039(4) 0.034(4) 0.033(4) 0.000(4) 0.010(3) 0.002(4) C13_1 0.024(3) 0.033(4) 0.032(4) 0.008(3) 0.002(3) 0.004(3) C14_1 0.032(4) 0.024(4) 0.026(4) 0.002(3) 0.004(3) 0.008(3) C15_1 0.021(4) 0.040(4) 0.027(4) 0.007(3) 0.005(3) 0.004(3) C16_1 0.034(4) 0.033(4) 0.034(4) 0.009(3) 0.006(3) 0.003(3) C17_1 0.023(4) 0.044(4) 0.030(4) 0.012(4) 0.002(3) 0.019(3) C18_1 0.010(4) 0.054(5) 0.046(4) -0.008(4) 0.005(3) -0.001(3) C19_1 0.024(5) 0.040(4) 0.067(5) 0.007(4) -0.003(4) 0.004(3) C20_1 0.027(4) 0.034(4) 0.059(5) -0.002(4) 0.005(3) 0.007(3) C21_1 0.024(4) 0.044(5) 0.128(8) 0.016(5) 0.011(5) -0.002(4) C22_1 0.036(4) 0.028(4) 0.036(4) -0.005(4) 0.005(3) 0.000(4) C23_1 0.037(4) 0.036(4) 0.029(4) -0.003(3) -0.003(3) -0.008(3) C24_1 0.057(5) 0.053(5) 0.047(5) -0.003(5) 0.004(4) -0.005(5) C25_1 0.086(7) 0.068(6) 0.030(4) -0.001(4) -0.010(5) -0.003(6) C26_1 0.075(7) 0.059(6) 0.055(6) 0.013(5) -0.022(5) -0.011(5) C27_1 0.044(5) 0.055(5) 0.071(6) 0.006(5) -0.014(5) 0.012(4) C28_1 0.038(4) 0.044(5) 0.045(5) -0.006(4) -0.001(4) 0.001(4) P1_2 0.0405(11) 0.0256(10) 0.0328(10) 0.0043(9) 0.0097(8) 0.0046(9) O1_2 0.057(3) 0.025(3) 0.047(3) 0.012(2) 0.017(2) 0.006(2) O2_2 0.106(5) 0.045(4) 0.128(6) 0.035(4) 0.077(4) 0.045(3) O3_2 0.070(3) 0.072(4) 0.026(3) -0.006(3) 0.002(3) 0.012(3) N1_2 0.031(3) 0.027(3) 0.038(3) -0.004(3) 0.005(3) 0.010(3) C1_2 0.036(4) 0.039(5) 0.026(4) 0.012(4) 0.005(3) 0.008(4) C2_2 0.039(5) 0.043(5) 0.047(5) 0.003(4) 0.008(4) 0.012(4) C3_2 0.033(5) 0.043(5) 0.059(5) -0.005(4) 0.004(4) 0.001(4) C4_2 0.043(5) 0.055(6) 0.036(5) -0.001(4) -0.004(4) -0.009(5) C5_2 0.045(5) 0.053(6) 0.058(5) 0.004(4) 0.012(4) 0.019(4) C6_2 0.053(5) 0.041(5) 0.036(4) 0.003(4) 0.007(4) 0.019(4) C13_2 0.030(3) 0.030(4) 0.026(3) -0.003(3) 0.003(3) 0.005(3) C14_2 0.040(4) 0.018(4) 0.025(4) -0.005(3) 0.005(3) 0.001(3) C15_2 0.035(4) 0.019(4) 0.032(4) -0.003(3) 0.005(3) 0.004(3) C16_2 0.029(4) 0.055(5) 0.034(4) -0.003(3) 0.005(3) 0.000(3) C17_2 0.043(4) 0.070(6) 0.031(4) -0.008(4) 0.010(4) 0.001(4) C18_2 0.055(5) 0.054(6) 0.025(4) -0.003(4) 0.006(4) 0.002(4) C19_2 0.038(4) 0.050(5) 0.041(5) 0.000(4) 0.006(4) 0.024(4) C20_2 0.074(6) 0.038(5) 0.030(4) -0.007(3) 0.013(4) 0.016(4) C21_2 0.111(7) 0.099(8) 0.024(4) -0.011(5) 0.006(5) 0.020(6) C22_2 0.054(5) 0.056(6) 0.033(4) 0.009(4) 0.024(4) 0.028(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1_1 O1_1 1.495(4) . ? P1_1 C7_1 1.793(6) . ? P1_1 C1_1 1.798(6) . ? P1_1 C13_1 1.816(6) . ? O2_1 C22_1 1.225(8) . ? O3_1 C18_1 1.383(7) . ? O3_1 C21_1 1.420(8) . ? N1_1 C22_1 1.329(8) . ? N1_1 C14_1 1.458(8) . ? N1_1 H1_1 0.8800 . ? C1_1 C2_1 1.387(9) . ? C1_1 C6_1 1.396(9) . ? C2_1 C3_1 1.391(9) . ? C2_1 H2_1 0.9500 . ? C3_1 C4_1 1.388(10) . ? C3_1 H3_1 0.9500 . ? C4_1 C5_1 1.350(10) . ? C4_1 H4_1 0.9500 . ? C5_1 C6_1 1.380(9) . ? C5_1 H5_1 0.9500 . ? C6_1 H6_1 0.9500 . ? C7_1 C8_1 1.401(9) . ? C7_1 C12_1 1.409(9) . ? C8_1 C9_1 1.350(9) . ? C8_1 H8_1 0.9500 . ? C9_1 C10_1 1.389(10) . ? C9_1 H9_1 0.9500 . ? C10_1 C11_1 1.384(11) . ? C10_1 H10_1 0.9500 . ? C11_1 C12_1 1.376(9) . ? C11_1 H11_1 0.9500 . ? C12_1 H12_1 0.9500 . ? C13_1 C14_1 1.548(8) . ? C13_1 H13A_1 0.9900 . ? C13_1 H13B_1 0.9900 . ? C14_1 C15_1 1.510(8) . ? C14_1 H14_1 1.0000 . ? C15_1 C16_1 1.385(8) . ? C15_1 C20_1 1.399(9) . ? C16_1 C17_1 1.389(8) . ? C16_1 H16_1 0.9500 . ? C17_1 C18_1 1.428(10) . ? C17_1 H17_1 0.9500 . ? C18_1 C19_1 1.388(9) . ? C19_1 C20_1 1.365(9) . ? C19_1 H19_1 0.9500 . ? C20_1 H20_1 0.9500 . ? C21_1 H21A_1 0.9800 . ? C21_1 H21B_1 0.9800 . ? C21_1 H21C_1 0.9800 . ? C22_1 C23_1 1.500(9) . ? C23_1 C28_1 1.378(9) . ? C23_1 C24_1 1.392(10) . ? C24_1 C25_1 1.378(11) . ? C24_1 H24_1 0.9500 . ? C25_1 C26_1 1.341(12) . ? C25_1 H25_1 0.9500 . ? C26_1 C27_1 1.386(12) . ? C26_1 H26_1 0.9500 . ? C27_1 C28_1 1.408(10) . ? C27_1 H27_1 0.9500 . ? C28_1 H28_1 0.9500 . ? P1_2 O1_2 1.495(5) . ? P1_2 C7_2 1.779(6) . ? P1_2 C13_2 1.797(6) . ? P1_2 C1_2 1.811(7) . ? P1_2 C7'_2 1.852(9) . ? O2_2 C22_2 1.244(9) . ? O3_2 C18_2 1.376(8) . ? O3_2 C21_2 1.428(8) . ? N1_2 C22_2 1.332(8) . ? N1_2 C14_2 1.441(8) . ? N1_2 H1_2 0.8800 . ? C1_2 C6_2 1.368(9) . ? C1_2 C2_2 1.387(10) . ? C2_2 C3_2 1.384(10) . ? C2_2 H2_2 0.9500 . ? C3_2 C4_2 1.369(10) . ? C3_2 H3_2 0.9500 . ? C4_2 C5_2 1.404(11) . ? C4_2 H4_2 0.9500 . ? C5_2 C6_2 1.366(10) . ? C5_2 H5_2 0.9500 . ? C6_2 H6_2 0.9500 . ? C7_2 C8_2 1.3900 . ? C7_2 C12_2 1.3900 . ? C8_2 C9_2 1.3900 . ? C8_2 H8_2 0.9500 . ? C9_2 C10_2 1.3900 . ? C9_2 H9_2 0.9500 . ? C10_2 C11_2 1.3900 . ? C10_2 H10_2 0.9500 . ? C11_2 C12_2 1.3900 . ? C11_2 H11_2 0.9500 . ? C12_2 H12_2 0.9500 . ? C7'_2 C8'_2 1.3900 . ? C7'_2 C12'_2 1.3900 . ? C8'_2 C9'_2 1.3900 . ? C8'_2 H8'_2 0.9500 . ? C9'_2 C10'_2 1.3900 . ? C9'_2 H9'_2 0.9500 . ? C10'_2 C11'_2 1.3900 . ? C10'_2 H10'_2 0.9500 . ? C11'_2 C12'_2 1.3900 . ? C11'_2 H11'_2 0.9500 . ? C12'_2 H12'_2 0.9500 . ? C13_2 C14_2 1.546(8) . ? C13_2 H13A_2 0.9900 . ? C13_2 H13B_2 0.9900 . ? C14_2 C15_2 1.535(9) . ? C14_2 H14_2 1.0000 . ? C15_2 C20_2 1.364(9) . ? C15_2 C16_2 1.377(9) . ? C16_2 C17_2 1.384(9) . ? C16_2 H16_2 0.9500 . ? C17_2 C18_2 1.371(10) . ? C17_2 H17_2 0.9500 . ? C18_2 C19_2 1.381(9) . ? C19_2 C20_2 1.390(10) . ? C19_2 H19_2 0.9500 . ? C20_2 H20_2 0.9500 . ? C21_2 H21A_2 0.9800 . ? C21_2 H21B_2 0.9800 . ? C21_2 H21C_2 0.9800 . ? C22_2 C23_2 1.473(9) . ? C22_2 C23'_2 1.478(9) . ? C23_2 C24_2 1.3900 . ? C23_2 C28_2 1.3900 . ? C24_2 C25_2 1.3900 . ? C24_2 H24_2 0.9500 . ? C25_2 C26_2 1.3900 . ? C25_2 H25_2 0.9500 . ? C26_2 C27_2 1.3900 . ? C26_2 H26_2 0.9500 . ? C27_2 C28_2 1.3900 . ? C27_2 H27_2 0.9500 . ? C28_2 H28_2 0.9500 . ? C23'_2 C24'_2 1.3900 . ? C23'_2 C28'_2 1.3900 . ? C24'_2 C25'_2 1.3900 . ? C24'_2 H24'_2 0.9500 . ? C25'_2 C26'_2 1.3900 . ? C25'_2 H25'_2 0.9500 . ? C26'_2 C27'_2 1.3900 . ? C26'_2 H26'_2 0.9500 . ? C27'_2 C28'_2 1.3900 . ? C27'_2 H27'_2 0.9500 . ? C28'_2 H28'_2 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 O1_1 P1_1 C7_1 112.0(3) . . ? O1_1 P1_1 C1_1 112.1(3) . . ? C7_1 P1_1 C1_1 107.7(3) . . ? O1_1 P1_1 C13_1 111.1(3) . . ? C7_1 P1_1 C13_1 108.8(3) . . ? C1_1 P1_1 C13_1 104.8(3) . . ? C18_1 O3_1 C21_1 116.7(6) . . ? C22_1 N1_1 C14_1 119.9(5) . . ? C22_1 N1_1 H1_1 120.0 . . ? C14_1 N1_1 H1_1 120.0 . . ? C2_1 C1_1 C6_1 118.6(6) . . ? C2_1 C1_1 P1_1 123.2(5) . . ? C6_1 C1_1 P1_1 118.2(5) . . ? C1_1 C2_1 C3_1 121.3(6) . . ? C1_1 C2_1 H2_1 119.4 . . ? C3_1 C2_1 H2_1 119.4 . . ? C4_1 C3_1 C2_1 119.0(7) . . ? C4_1 C3_1 H3_1 120.5 . . ? C2_1 C3_1 H3_1 120.5 . . ? C5_1 C4_1 C3_1 119.5(6) . . ? C5_1 C4_1 H4_1 120.2 . . ? C3_1 C4_1 H4_1 120.2 . . ? C4_1 C5_1 C6_1 122.6(7) . . ? C4_1 C5_1 H5_1 118.7 . . ? C6_1 C5_1 H5_1 118.7 . . ? C5_1 C6_1 C1_1 119.0(7) . . ? C5_1 C6_1 H6_1 120.5 . . ? C1_1 C6_1 H6_1 120.5 . . ? C8_1 C7_1 C12_1 118.4(6) . . ? C8_1 C7_1 P1_1 123.6(5) . . ? C12_1 C7_1 P1_1 118.0(5) . . ? C9_1 C8_1 C7_1 119.7(7) . . ? C9_1 C8_1 H8_1 120.1 . . ? C7_1 C8_1 H8_1 120.1 . . ? C8_1 C9_1 C10_1 122.1(7) . . ? C8_1 C9_1 H9_1 118.9 . . ? C10_1 C9_1 H9_1 119.0 . . ? C11_1 C10_1 C9_1 119.3(7) . . ? C11_1 C10_1 H10_1 120.3 . . ? C9_1 C10_1 H10_1 120.3 . . ? C12_1 C11_1 C10_1 119.5(7) . . ? C12_1 C11_1 H11_1 120.3 . . ? C10_1 C11_1 H11_1 120.3 . . ? C11_1 C12_1 C7_1 121.0(7) . . ? C11_1 C12_1 H12_1 119.5 . . ? C7_1 C12_1 H12_1 119.5 . . ? C14_1 C13_1 P1_1 112.2(4) . . ? C14_1 C13_1 H13A_1 109.2 . . ? P1_1 C13_1 H13A_1 109.2 . . ? C14_1 C13_1 H13B_1 109.2 . . ? P1_1 C13_1 H13B_1 109.2 . . ? H13A_1 C13_1 H13B_1 107.9 . . ? N1_1 C14_1 C15_1 113.6(5) . . ? N1_1 C14_1 C13_1 109.3(5) . . ? C15_1 C14_1 C13_1 113.2(5) . . ? N1_1 C14_1 H14_1 106.7 . . ? C15_1 C14_1 H14_1 106.7 . . ? C13_1 C14_1 H14_1 106.7 . . ? C16_1 C15_1 C20_1 117.4(6) . . ? C16_1 C15_1 C14_1 118.9(6) . . ? C20_1 C15_1 C14_1 123.7(6) . . ? C15_1 C16_1 C17_1 123.8(6) . . ? C15_1 C16_1 H16_1 118.1 . . ? C17_1 C16_1 H16_1 118.1 . . ? C16_1 C17_1 C18_1 116.5(6) . . ? C16_1 C17_1 H17_1 121.7 . . ? C18_1 C17_1 H17_1 121.7 . . ? O3_1 C18_1 C19_1 117.5(7) . . ? O3_1 C18_1 C17_1 122.1(6) . . ? C19_1 C18_1 C17_1 120.2(6) . . ? C20_1 C19_1 C18_1 120.6(7) . . ? C20_1 C19_1 H19_1 119.7 . . ? C18_1 C19_1 H19_1 119.7 . . ? C19_1 C20_1 C15_1 121.4(6) . . ? C19_1 C20_1 H20_1 119.3 . . ? C15_1 C20_1 H20_1 119.3 . . ? O3_1 C21_1 H21A_1 109.5 . . ? O3_1 C21_1 H21B_1 109.5 . . ? H21A_1 C21_1 H21B_1 109.5 . . ? O3_1 C21_1 H21C_1 109.5 . . ? H21A_1 C21_1 H21C_1 109.5 . . ? H21B_1 C21_1 H21C_1 109.5 . . ? O2_1 C22_1 N1_1 122.9(6) . . ? O2_1 C22_1 C23_1 118.8(6) . . ? N1_1 C22_1 C23_1 118.3(6) . . ? C28_1 C23_1 C24_1 119.3(6) . . ? C28_1 C23_1 C22_1 122.5(6) . . ? C24_1 C23_1 C22_1 118.1(6) . . ? C25_1 C24_1 C23_1 118.9(8) . . ? C25_1 C24_1 H24_1 120.5 . . ? C23_1 C24_1 H24_1 120.5 . . ? C26_1 C25_1 C24_1 122.1(8) . . ? C26_1 C25_1 H25_1 118.9 . . ? C24_1 C25_1 H25_1 118.9 . . ? C25_1 C26_1 C27_1 120.8(8) . . ? C25_1 C26_1 H26_1 119.6 . . ? C27_1 C26_1 H26_1 119.6 . . ? C26_1 C27_1 C28_1 117.9(8) . . ? C26_1 C27_1 H27_1 121.1 . . ? C28_1 C27_1 H27_1 121.1 . . ? C23_1 C28_1 C27_1 120.9(7) . . ? C23_1 C28_1 H28_1 119.5 . . ? C27_1 C28_1 H28_1 119.5 . . ? O1_2 P1_2 C7_2 114.6(3) . . ? O1_2 P1_2 C13_2 111.5(3) . . ? C7_2 P1_2 C13_2 105.8(3) . . ? O1_2 P1_2 C1_2 111.1(3) . . ? C7_2 P1_2 C1_2 103.2(4) . . ? C13_2 P1_2 C1_2 110.2(3) . . ? O1_2 P1_2 C7'_2 106.2(5) . . ? C7_2 P1_2 C7'_2 9.7(6) . . ? C13_2 P1_2 C7'_2 106.0(5) . . ? C1_2 P1_2 C7'_2 111.7(5) . . ? C18_2 O3_2 C21_2 117.7(6) . . ? C22_2 N1_2 C14_2 123.2(6) . . ? C22_2 N1_2 H1_2 118.4 . . ? C14_2 N1_2 H1_2 118.4 . . ? C6_2 C1_2 C2_2 119.5(7) . . ? C6_2 C1_2 P1_2 118.3(6) . . ? C2_2 C1_2 P1_2 122.0(5) . . ? C3_2 C2_2 C1_2 119.7(7) . . ? C3_2 C2_2 H2_2 120.2 . . ? C1_2 C2_2 H2_2 120.2 . . ? C4_2 C3_2 C2_2 121.0(7) . . ? C4_2 C3_2 H3_2 119.5 . . ? C2_2 C3_2 H3_2 119.5 . . ? C3_2 C4_2 C5_2 118.8(7) . . ? C3_2 C4_2 H4_2 120.6 . . ? C5_2 C4_2 H4_2 120.6 . . ? C6_2 C5_2 C4_2 120.0(8) . . ? C6_2 C5_2 H5_2 120.0 . . ? C4_2 C5_2 H5_2 120.0 . . ? C5_2 C6_2 C1_2 121.1(8) . . ? C5_2 C6_2 H6_2 119.4 . . ? C1_2 C6_2 H6_2 119.4 . . ? C8_2 C7_2 C12_2 120.0 . . ? C8_2 C7_2 P1_2 123.4(5) . . ? C12_2 C7_2 P1_2 116.5(5) . . ? C9_2 C8_2 C7_2 120.0 . . ? C9_2 C8_2 H8_2 120.0 . . ? C7_2 C8_2 H8_2 120.0 . . ? C8_2 C9_2 C10_2 120.0 . . ? C8_2 C9_2 H9_2 120.0 . . ? C10_2 C9_2 H9_2 120.0 . . ? C11_2 C10_2 C9_2 120.0 . . ? C11_2 C10_2 H10_2 120.0 . . ? C9_2 C10_2 H10_2 120.0 . . ? C10_2 C11_2 C12_2 120.0 . . ? C10_2 C11_2 H11_2 120.0 . . ? C12_2 C11_2 H11_2 120.0 . . ? C11_2 C12_2 C7_2 120.0 . . ? C11_2 C12_2 H12_2 120.0 . . ? C7_2 C12_2 H12_2 120.0 . . ? C8'_2 C7'_2 C12'_2 120.0 . . ? C8'_2 C7'_2 P1_2 120.6(8) . . ? C12'_2 C7'_2 P1_2 119.2(8) . . ? C9'_2 C8'_2 C7'_2 120.0 . . ? C9'_2 C8'_2 H8'_2 120.0 . . ? C7'_2 C8'_2 H8'_2 120.0 . . ? C8'_2 C9'_2 C10'_2 120.0 . . ? C8'_2 C9'_2 H9'_2 120.0 . . ? C10'_2 C9'_2 H9'_2 120.0 . . ? C11'_2 C10'_2 C9'_2 120.0 . . ? C11'_2 C10'_2 H10'_2 120.0 . . ? C9'_2 C10'_2 H10'_2 120.0 . . ? C10'_2 C11'_2 C12'_2 120.0 . . ? C10'_2 C11'_2 H11'_2 120.0 . . ? C12'_2 C11'_2 H11'_2 120.0 . . ? C11'_2 C12'_2 C7'_2 120.0 . . ? C11'_2 C12'_2 H12'_2 120.0 . . ? C7'_2 C12'_2 H12'_2 120.0 . . ? C14_2 C13_2 P1_2 111.8(4) . . ? C14_2 C13_2 H13A_2 109.3 . . ? P1_2 C13_2 H13A_2 109.3 . . ? C14_2 C13_2 H13B_2 109.3 . . ? P1_2 C13_2 H13B_2 109.3 . . ? H13A_2 C13_2 H13B_2 107.9 . . ? N1_2 C14_2 C15_2 110.6(5) . . ? N1_2 C14_2 C13_2 110.3(5) . . ? C15_2 C14_2 C13_2 114.8(5) . . ? N1_2 C14_2 H14_2 106.9 . . ? C15_2 C14_2 H14_2 106.9 . . ? C13_2 C14_2 H14_2 106.9 . . ? C20_2 C15_2 C16_2 118.1(6) . . ? C20_2 C15_2 C14_2 123.8(6) . . ? C16_2 C15_2 C14_2 118.1(6) . . ? C15_2 C16_2 C17_2 121.7(7) . . ? C15_2 C16_2 H16_2 119.2 . . ? C17_2 C16_2 H16_2 119.2 . . ? C18_2 C17_2 C16_2 119.6(7) . . ? C18_2 C17_2 H17_2 120.2 . . ? C16_2 C17_2 H17_2 120.2 . . ? C17_2 C18_2 O3_2 125.7(7) . . ? C17_2 C18_2 C19_2 119.6(6) . . ? O3_2 C18_2 C19_2 114.7(6) . . ? C18_2 C19_2 C20_2 119.7(7) . . ? C18_2 C19_2 H19_2 120.2 . . ? C20_2 C19_2 H19_2 120.2 . . ? C15_2 C20_2 C19_2 121.3(7) . . ? C15_2 C20_2 H20_2 119.3 . . ? C19_2 C20_2 H20_2 119.3 . . ? O3_2 C21_2 H21A_2 109.5 . . ? O3_2 C21_2 H21B_2 109.5 . . ? H21A_2 C21_2 H21B_2 109.5 . . ? O3_2 C21_2 H21C_2 109.5 . . ? H21A_2 C21_2 H21C_2 109.5 . . ? H21B_2 C21_2 H21C_2 109.5 . . ? O2_2 C22_2 N1_2 122.2(8) . . ? O2_2 C22_2 C23_2 117.7(8) . . ? N1_2 C22_2 C23_2 119.6(8) . . ? O2_2 C22_2 C23'_2 123.8(8) . . ? N1_2 C22_2 C23'_2 113.9(7) . . ? C23_2 C22_2 C23'_2 8.2(6) . . ? C24_2 C23_2 C28_2 120.0 . . ? C24_2 C23_2 C22_2 117.1(7) . . ? C28_2 C23_2 C22_2 121.4(7) . . ? C23_2 C24_2 C25_2 120.0 . . ? C23_2 C24_2 H24_2 120.0 . . ? C25_2 C24_2 H24_2 120.0 . . ? C24_2 C25_2 C26_2 120.0 . . ? C24_2 C25_2 H25_2 120.0 . . ? C26_2 C25_2 H25_2 120.0 . . ? C27_2 C26_2 C25_2 120.0 . . ? C27_2 C26_2 H26_2 120.0 . . ? C25_2 C26_2 H26_2 120.0 . . ? C26_2 C27_2 C28_2 120.0 . . ? C26_2 C27_2 H27_2 120.0 . . ? C28_2 C27_2 H27_2 120.0 . . ? C27_2 C28_2 C23_2 120.0 . . ? C27_2 C28_2 H28_2 120.0 . . ? C23_2 C28_2 H28_2 120.0 . . ? C24'_2 C23'_2 C28'_2 120.0 . . ? C24'_2 C23'_2 C22_2 119.2(7) . . ? C28'_2 C23'_2 C22_2 120.7(7) . . ? C25'_2 C24'_2 C23'_2 120.0 . . ? C25'_2 C24'_2 H24'_2 120.0 . . ? C23'_2 C24'_2 H24'_2 120.0 . . ? C24'_2 C25'_2 C26'_2 120.0 . . ? C24'_2 C25'_2 H25'_2 120.0 . . ? C26'_2 C25'_2 H25'_2 120.0 . . ? C27'_2 C26'_2 C25'_2 120.0 . . ? C27'_2 C26'_2 H26'_2 120.0 . . ? C25'_2 C26'_2 H26'_2 120.0 . . ? C26'_2 C27'_2 C28'_2 120.0 . . ? C26'_2 C27'_2 H27'_2 120.0 . . ? C28'_2 C27'_2 H27'_2 120.0 . . ? C27'_2 C28'_2 C23'_2 120.0 . . ? C27'_2 C28'_2 H28'_2 120.0 . . ? C23'_2 C28'_2 H28'_2 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1_1 P1_1 C1_1 C2_1 156.4(5) . . . . ? C7_1 P1_1 C1_1 C2_1 -80.0(6) . . . . ? C13_1 P1_1 C1_1 C2_1 35.7(6) . . . . ? O1_1 P1_1 C1_1 C6_1 -25.8(6) . . . . ? C7_1 P1_1 C1_1 C6_1 97.8(5) . . . . ? C13_1 P1_1 C1_1 C6_1 -146.4(5) . . . . ? C6_1 C1_1 C2_1 C3_1 2.5(10) . . . . ? P1_1 C1_1 C2_1 C3_1 -179.6(5) . . . . ? C1_1 C2_1 C3_1 C4_1 -1.6(11) . . . . ? C2_1 C3_1 C4_1 C5_1 1.1(11) . . . . ? C3_1 C4_1 C5_1 C6_1 -1.5(11) . . . . ? C4_1 C5_1 C6_1 C1_1 2.4(10) . . . . ? C2_1 C1_1 C6_1 C5_1 -2.9(9) . . . . ? P1_1 C1_1 C6_1 C5_1 179.2(5) . . . . ? O1_1 P1_1 C7_1 C8_1 -173.5(5) . . . . ? C1_1 P1_1 C7_1 C8_1 62.8(6) . . . . ? C13_1 P1_1 C7_1 C8_1 -50.3(6) . . . . ? O1_1 P1_1 C7_1 C12_1 7.5(6) . . . . ? C1_1 P1_1 C7_1 C12_1 -116.2(5) . . . . ? C13_1 P1_1 C7_1 C12_1 130.7(5) . . . . ? C12_1 C7_1 C8_1 C9_1 -0.3(10) . . . . ? P1_1 C7_1 C8_1 C9_1 -179.3(5) . . . . ? C7_1 C8_1 C9_1 C10_1 1.1(11) . . . . ? C8_1 C9_1 C10_1 C11_1 -1.3(11) . . . . ? C9_1 C10_1 C11_1 C12_1 0.6(11) . . . . ? C10_1 C11_1 C12_1 C7_1 0.2(10) . . . . ? C8_1 C7_1 C12_1 C11_1 -0.4(9) . . . . ? P1_1 C7_1 C12_1 C11_1 178.7(5) . . . . ? O1_1 P1_1 C13_1 C14_1 39.0(5) . . . . ? C7_1 P1_1 C13_1 C14_1 -84.7(5) . . . . ? C1_1 P1_1 C13_1 C14_1 160.3(4) . . . . ? C22_1 N1_1 C14_1 C15_1 -96.1(7) . . . . ? C22_1 N1_1 C14_1 C13_1 136.4(6) . . . . ? P1_1 C13_1 C14_1 N1_1 -154.6(4) . . . . ? P1_1 C13_1 C14_1 C15_1 77.7(6) . . . . ? N1_1 C14_1 C15_1 C16_1 141.7(6) . . . . ? C13_1 C14_1 C15_1 C16_1 -92.9(7) . . . . ? N1_1 C14_1 C15_1 C20_1 -37.6(9) . . . . ? C13_1 C14_1 C15_1 C20_1 87.9(7) . . . . ? C20_1 C15_1 C16_1 C17_1 -2.2(9) . . . . ? C14_1 C15_1 C16_1 C17_1 178.5(6) . . . . ? C15_1 C16_1 C17_1 C18_1 1.8(9) . . . . ? C21_1 O3_1 C18_1 C19_1 -177.7(7) . . . . ? C21_1 O3_1 C18_1 C17_1 7.1(10) . . . . ? C16_1 C17_1 C18_1 O3_1 175.5(6) . . . . ? C16_1 C17_1 C18_1 C19_1 0.4(10) . . . . ? O3_1 C18_1 C19_1 C20_1 -177.6(7) . . . . ? C17_1 C18_1 C19_1 C20_1 -2.3(11) . . . . ? C18_1 C19_1 C20_1 C15_1 2.0(11) . . . . ? C16_1 C15_1 C20_1 C19_1 0.2(10) . . . . ? C14_1 C15_1 C20_1 C19_1 179.5(6) . . . . ? C14_1 N1_1 C22_1 O2_1 3.0(10) . . . . ? C14_1 N1_1 C22_1 C23_1 -176.2(6) . . . . ? O2_1 C22_1 C23_1 C28_1 -153.0(7) . . . . ? N1_1 C22_1 C23_1 C28_1 26.2(10) . . . . ? O2_1 C22_1 C23_1 C24_1 23.0(10) . . . . ? N1_1 C22_1 C23_1 C24_1 -157.8(6) . . . . ? C28_1 C23_1 C24_1 C25_1 -0.7(11) . . . . ? C22_1 C23_1 C24_1 C25_1 -176.8(7) . . . . ? C23_1 C24_1 C25_1 C26_1 1.2(13) . . . . ? C24_1 C25_1 C26_1 C27_1 0.0(14) . . . . ? C25_1 C26_1 C27_1 C28_1 -1.6(13) . . . . ? C24_1 C23_1 C28_1 C27_1 -0.8(11) . . . . ? C22_1 C23_1 C28_1 C27_1 175.1(7) . . . . ? C26_1 C27_1 C28_1 C23_1 2.0(12) . . . . ? O1_2 P1_2 C1_2 C6_2 -3.6(6) . . . . ? C7_2 P1_2 C1_2 C6_2 119.7(6) . . . . ? C13_2 P1_2 C1_2 C6_2 -127.6(5) . . . . ? C7'_2 P1_2 C1_2 C6_2 114.8(7) . . . . ? O1_2 P1_2 C1_2 C2_2 -178.8(5) . . . . ? C7_2 P1_2 C1_2 C2_2 -55.6(6) . . . . ? C13_2 P1_2 C1_2 C2_2 57.1(6) . . . . ? C7'_2 P1_2 C1_2 C2_2 -60.5(8) . . . . ? C6_2 C1_2 C2_2 C3_2 1.3(10) . . . . ? P1_2 C1_2 C2_2 C3_2 176.5(5) . . . . ? C1_2 C2_2 C3_2 C4_2 -0.5(11) . . . . ? C2_2 C3_2 C4_2 C5_2 -0.7(12) . . . . ? C3_2 C4_2 C5_2 C6_2 0.9(12) . . . . ? C4_2 C5_2 C6_2 C1_2 -0.1(11) . . . . ? C2_2 C1_2 C6_2 C5_2 -1.1(10) . . . . ? P1_2 C1_2 C6_2 C5_2 -176.5(6) . . . . ? O1_2 P1_2 C7_2 C8_2 -151.4(5) . . . . ? C13_2 P1_2 C7_2 C8_2 -28.2(6) . . . . ? C1_2 P1_2 C7_2 C8_2 87.6(5) . . . . ? C7'_2 P1_2 C7_2 C8_2 -121(4) . . . . ? O1_2 P1_2 C7_2 C12_2 24.0(6) . . . . ? C13_2 P1_2 C7_2 C12_2 147.2(4) . . . . ? C1_2 P1_2 C7_2 C12_2 -97.0(5) . . . . ? C7'_2 P1_2 C7_2 C12_2 55(4) . . . . ? C12_2 C7_2 C8_2 C9_2 0.0 . . . . ? P1_2 C7_2 C8_2 C9_2 175.2(7) . . . . ? C7_2 C8_2 C9_2 C10_2 0.0 . . . . ? C8_2 C9_2 C10_2 C11_2 0.0 . . . . ? C9_2 C10_2 C11_2 C12_2 0.0 . . . . ? C10_2 C11_2 C12_2 C7_2 0.0 . . . . ? C8_2 C7_2 C12_2 C11_2 0.0 . . . . ? P1_2 C7_2 C12_2 C11_2 -175.5(7) . . . . ? O1_2 P1_2 C7'_2 C8'_2 -177.3(7) . . . . ? C7_2 P1_2 C7'_2 C8'_2 32(4) . . . . ? C13_2 P1_2 C7'_2 C8'_2 -58.7(8) . . . . ? C1_2 P1_2 C7'_2 C8'_2 61.4(8) . . . . ? O1_2 P1_2 C7'_2 C12'_2 8.5(9) . . . . ? C7_2 P1_2 C7'_2 C12'_2 -142(4) . . . . ? C13_2 P1_2 C7'_2 C12'_2 127.2(8) . . . . ? C1_2 P1_2 C7'_2 C12'_2 -112.8(8) . . . . ? C12'_2 C7'_2 C8'_2 C9'_2 0.0 . . . . ? P1_2 C7'_2 C8'_2 C9'_2 -174.1(10) . . . . ? C7'_2 C8'_2 C9'_2 C10'_2 0.0 . . . . ? C8'_2 C9'_2 C10'_2 C11'_2 0.0 . . . . ? C9'_2 C10'_2 C11'_2 C12'_2 0.0 . . . . ? C10'_2 C11'_2 C12'_2 C7'_2 0.0 . . . . ? C8'_2 C7'_2 C12'_2 C11'_2 0.0 . . . . ? P1_2 C7'_2 C12'_2 C11'_2 174.2(10) . . . . ? O1_2 P1_2 C13_2 C14_2 -48.0(5) . . . . ? C7_2 P1_2 C13_2 C14_2 -173.2(5) . . . . ? C1_2 P1_2 C13_2 C14_2 75.9(5) . . . . ? C7'_2 P1_2 C13_2 C14_2 -163.1(6) . . . . ? C22_2 N1_2 C14_2 C15_2 -112.9(7) . . . . ? C22_2 N1_2 C14_2 C13_2 119.0(6) . . . . ? P1_2 C13_2 C14_2 N1_2 -72.6(6) . . . . ? P1_2 C13_2 C14_2 C15_2 161.7(4) . . . . ? N1_2 C14_2 C15_2 C20_2 -123.3(7) . . . . ? C13_2 C14_2 C15_2 C20_2 2.3(9) . . . . ? N1_2 C14_2 C15_2 C16_2 56.0(8) . . . . ? C13_2 C14_2 C15_2 C16_2 -178.4(6) . . . . ? C20_2 C15_2 C16_2 C17_2 -1.1(11) . . . . ? C14_2 C15_2 C16_2 C17_2 179.5(6) . . . . ? C15_2 C16_2 C17_2 C18_2 0.6(11) . . . . ? C16_2 C17_2 C18_2 O3_2 179.4(7) . . . . ? C16_2 C17_2 C18_2 C19_2 0.2(11) . . . . ? C21_2 O3_2 C18_2 C17_2 3.5(11) . . . . ? C21_2 O3_2 C18_2 C19_2 -177.3(7) . . . . ? C17_2 C18_2 C19_2 C20_2 -0.4(11) . . . . ? O3_2 C18_2 C19_2 C20_2 -179.7(7) . . . . ? C16_2 C15_2 C20_2 C19_2 0.9(11) . . . . ? C14_2 C15_2 C20_2 C19_2 -179.8(7) . . . . ? C18_2 C19_2 C20_2 C15_2 -0.1(12) . . . . ? C14_2 N1_2 C22_2 O2_2 1.8(11) . . . . ? C14_2 N1_2 C22_2 C23_2 174.6(7) . . . . ? C14_2 N1_2 C22_2 C23'_2 -178.9(7) . . . . ? O2_2 C22_2 C23_2 C24_2 -146.8(7) . . . . ? N1_2 C22_2 C23_2 C24_2 40.1(9) . . . . ? C23'_2 C22_2 C23_2 C24_2 -7(4) . . . . ? O2_2 C22_2 C23_2 C28_2 19.5(11) . . . . ? N1_2 C22_2 C23_2 C28_2 -153.5(6) . . . . ? C23'_2 C22_2 C23_2 C28_2 159(5) . . . . ? C28_2 C23_2 C24_2 C25_2 0.0 . . . . ? C22_2 C23_2 C24_2 C25_2 166.6(9) . . . . ? C23_2 C24_2 C25_2 C26_2 0.0 . . . . ? C24_2 C25_2 C26_2 C27_2 0.0 . . . . ? C25_2 C26_2 C27_2 C28_2 0.0 . . . . ? C26_2 C27_2 C28_2 C23_2 0.0 . . . . ? C24_2 C23_2 C28_2 C27_2 0.0 . . . . ? C22_2 C23_2 C28_2 C27_2 -166.0(10) . . . . ? O2_2 C22_2 C23'_2 C24'_2 142.2(8) . . . . ? N1_2 C22_2 C23'_2 C24'_2 -37.1(10) . . . . ? C23_2 C22_2 C23'_2 C24'_2 99(5) . . . . ? O2_2 C22_2 C23'_2 C28'_2 -34.0(12) . . . . ? N1_2 C22_2 C23'_2 C28'_2 146.7(7) . . . . ? C23_2 C22_2 C23'_2 C28'_2 -78(5) . . . . ? C28'_2 C23'_2 C24'_2 C25'_2 0.0 . . . . ? C22_2 C23'_2 C24'_2 C25'_2 -176.2(11) . . . . ? C23'_2 C24'_2 C25'_2 C26'_2 0.0 . . . . ? C24'_2 C25'_2 C26'_2 C27'_2 0.0 . . . . ? C25'_2 C26'_2 C27'_2 C28'_2 0.0 . . . . ? C26'_2 C27'_2 C28'_2 C23'_2 0.0 . . . . ? C24'_2 C23'_2 C28'_2 C27'_2 0.0 . . . . ? C22_2 C23'_2 C28'_2 C27'_2 176.2(11) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 55.06 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.436 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.059 data_sw0003 _database_code_CSD 179763 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Warren, Stuart' 'Feeder, Neil' 'Fox, David J.' 'Medlock, Jonathan A.' _publ_contact_author_name 'Dr Stuart Warren' _publ_contact_author_address ; University Chemical Laboratory Lensfield Road Cambridge CB2 1EW UNITED KINGDOM ; _publ_contact_author_email 'SW134@CAM.AC.UK' _publ_section_title ; Synthesis, X-ray crystal structures and Horner-Wittig addition reactions of some protected beta-aminophosphine oxides ; _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C33 H34 N O3 P' _chemical_formula_weight 523.58 _chemical_melting_point ? _chemical_compound_source ? 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.1746(7) _cell_length_b 10.3826(5) _cell_length_c 17.3450(9) _cell_angle_alpha 90.00 _cell_angle_beta 93.820(3) _cell_angle_gamma 90.00 _cell_volume 2726.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 22575 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 25.03 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method ? _exptl_crystal_F_000 1112 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device NoniusKappaCCD _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13304 _diffrn_reflns_av_R_equivalents 0.0631 _diffrn_reflns_av_sigmaI/netI 0.0627 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4774 _reflns_number_observed 3511 _reflns_observed_criterion >2sigma(I) _computing_data_collection maXus _computing_cell_refinement maXus _computing_data_reduction maXus _computing_structure_solution teXsan _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 13 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.6474P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4761 _refine_ls_number_parameters 346 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_obs 0.0454 _refine_ls_wR_factor_all 0.1451 _refine_ls_wR_factor_obs 0.1083 _refine_ls_goodness_of_fit_all 1.041 _refine_ls_goodness_of_fit_obs 1.094 _refine_ls_restrained_S_all 1.243 _refine_ls_restrained_S_obs 1.094 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.01425(3) 0.21099(5) 0.72019(3) 0.0316(2) Uani 1 d . . O1 O -0.05693(8) 0.12200(13) 0.68952(8) 0.0384(4) Uani 1 d . . O2 O 0.25294(9) 0.05861(15) 0.66002(9) 0.0415(4) Uani 1 d . . H2O H 0.2837(15) 0.1209(23) 0.6682(13) 0.050 Uiso 1 d . . O3 O 0.11204(9) -0.24357(13) 0.81788(10) 0.0473(4) Uani 1 d . . N1 N 0.04963(10) -0.0614(2) 0.76897(10) 0.0336(4) Uani 1 d . . H1N H 0.00139(10) -0.0258(2) 0.74748(10) 0.040 Uiso 1 calc R . C1 C 0.12464(12) 0.1359(2) 0.72093(11) 0.0313(5) Uani 1 d . . H1 H 0.16587(12) 0.2006(2) 0.74628(11) 0.038 Uiso 1 calc R . C2 C 0.13042(12) 0.0154(2) 0.77606(12) 0.0318(5) Uani 1 d . . H2 H 0.17875(12) -0.0405(2) 0.75828(12) 0.038 Uiso 1 calc R . C3 C 0.15657(13) 0.0513(2) 0.86013(12) 0.0341(5) Uani 1 d . . C4 C 0.10573(14) 0.0243(2) 0.92090(13) 0.0409(5) Uani 1 d . . H4 H 0.05214(14) -0.0223(2) 0.91198(13) 0.049 Uiso 1 calc R . C5 C 0.1322(2) 0.0648(2) 0.99530(14) 0.0500(6) Uani 1 d . . H5 H 0.0961(2) 0.0470(2) 1.03672(14) 0.060 Uiso 1 calc R . C6 C 0.2103(2) 0.1305(2) 1.00922(15) 0.0556(7) Uani 1 d . . H6 H 0.2276(2) 0.1601(2) 1.05980(15) 0.067 Uiso 1 calc R . C7 C 0.2635(2) 0.1531(2) 0.94887(14) 0.0529(6) Uani 1 d . . H7 H 0.3187(2) 0.1952(2) 0.95836(14) 0.064 Uiso 1 calc R . C8 C 0.23646(14) 0.1146(2) 0.87508(13) 0.0431(6) Uani 1 d . . H8 H 0.27297(14) 0.1316(2) 0.83385(13) 0.052 Uiso 1 calc R . C9 C 0.16415(12) 0.1046(2) 0.64171(12) 0.0349(5) Uani 1 d . . C10 C 0.11559(14) -0.0050(2) 0.59822(12) 0.0406(5) Uani 1 d . . H10A H 0.05218(14) 0.0172(2) 0.59040(12) 0.049 Uiso 1 calc R . H10B H 0.12047(14) -0.0841(2) 0.63012(12) 0.049 Uiso 1 calc R . C11 C 0.1520(2) -0.0323(2) 0.51968(14) 0.0541(6) Uani 1 d . . H11A H 0.2126(2) -0.0673(2) 0.52774(14) 0.065 Uiso 1 calc R . H11B H 0.1148(2) -0.0984(2) 0.49221(14) 0.065 Uiso 1 calc R . C12 C 0.1539(2) 0.0876(3) 0.47015(15) 0.0652(8) Uani 1 d . . H12A H 0.1817(2) 0.0675(3) 0.42151(15) 0.078 Uiso 1 calc R . H12B H 0.0928(2) 0.1172(3) 0.45676(15) 0.078 Uiso 1 calc R . C13 C 0.2054(2) 0.1935(2) 0.51278(15) 0.0582(7) Uani 1 d . . H13A H 0.2040(2) 0.2721(2) 0.48044(15) 0.070 Uiso 1 calc R . H13B H 0.2678(2) 0.1665(2) 0.52200(15) 0.070 Uiso 1 calc R . C14 C 0.16725(14) 0.2239(2) 0.59000(13) 0.0430(6) Uani 1 d . . H14A H 0.10676(14) 0.2586(2) 0.58037(13) 0.052 Uiso 1 calc R . H14B H 0.20380(14) 0.2910(2) 0.61712(13) 0.052 Uiso 1 calc R . C15 C 0.04555(13) -0.1839(2) 0.79380(12) 0.0340(5) Uani 1 d . . C16 C -0.04530(13) -0.2414(2) 0.79372(12) 0.0338(5) Uani 1 d . . C17 C -0.05355(15) -0.3641(2) 0.82323(13) 0.0431(6) Uani 1 d . . H17 H -0.00207(15) -0.4104(2) 0.84087(13) 0.052 Uiso 1 calc R . C18 C -0.1357(2) -0.4207(2) 0.82748(15) 0.0529(6) Uani 1 d . . H18 H -0.1400(2) -0.5048(2) 0.84841(15) 0.064 Uiso 1 calc R . C19 C -0.2108(2) -0.3562(2) 0.80172(14) 0.0528(6) Uani 1 d . . H19 H -0.2671(2) -0.3950(2) 0.80489(14) 0.063 Uiso 1 calc R . C20 C -0.2036(2) -0.2340(2) 0.7711(2) 0.0567(7) Uani 1 d . . H20 H -0.2552(2) -0.1887(2) 0.7528(2) 0.068 Uiso 1 calc R . C21 C -0.12172(14) -0.1773(2) 0.76685(14) 0.0477(6) Uani 1 d . . H21 H -0.11757(14) -0.0935(2) 0.74537(14) 0.057 Uiso 1 calc R . C22 C 0.00067(14) 0.2533(2) 0.81993(12) 0.0351(5) Uani 1 d . . C23 C -0.07489(15) 0.2070(2) 0.85181(14) 0.0450(6) Uani 1 d . . H23 H -0.11579(15) 0.1557(2) 0.82142(14) 0.054 Uiso 1 calc R . C24 C -0.0907(2) 0.2353(3) 0.9277(2) 0.0602(7) Uani 1 d . . H24 H -0.1423(2) 0.2033(3) 0.9492(2) 0.072 Uiso 1 calc R . C25 C -0.0324(2) 0.3089(3) 0.9717(2) 0.0647(8) Uani 1 d . . H25 H -0.0436(2) 0.3279(3) 1.0237(2) 0.078 Uiso 1 calc R . C26 C 0.0432(2) 0.3561(2) 0.94086(14) 0.0572(7) Uani 1 d . . H26 H 0.0835(2) 0.4075(2) 0.97173(14) 0.069 Uiso 1 calc R . C27 C 0.0601(2) 0.3282(2) 0.86493(12) 0.0427(6) Uani 1 d . . H27 H 0.1120(2) 0.3601(2) 0.84383(12) 0.051 Uiso 1 calc R . C28 C 0.00651(12) 0.3639(2) 0.67036(11) 0.0316(5) Uani 1 d . . C29 C -0.0655(2) 0.3790(2) 0.61773(14) 0.0541(7) Uani 1 d . . H29 H -0.1042(2) 0.3086(2) 0.60619(14) 0.065 Uiso 1 calc R . C30 C -0.0811(2) 0.4970(3) 0.5819(2) 0.0768(9) Uani 1 d . . H30 H -0.1303(2) 0.5070(3) 0.5457(2) 0.092 Uiso 1 calc R . C31 C -0.0259(2) 0.5990(2) 0.5985(2) 0.0612(7) Uani 1 d . . H31 H -0.0368(2) 0.6794(2) 0.5735(2) 0.073 Uiso 1 calc R . C32 C 0.04469(14) 0.5854(2) 0.65080(13) 0.0425(5) Uani 1 d . . H32 H 0.08227(14) 0.6568(2) 0.66272(13) 0.051 Uiso 1 calc R . C33 C 0.06181(13) 0.4683(2) 0.68651(12) 0.0380(5) Uani 1 d . . H33 H 0.11163(13) 0.4592(2) 0.72226(12) 0.046 Uiso 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 0.0239(3) 0.0292(3) 0.0411(3) 0.0022(2) -0.0013(2) 0.0016(2) O1 0.0252(7) 0.0336(8) 0.0553(9) 0.0025(7) -0.0057(7) -0.0014(6) O2 0.0245(8) 0.0372(8) 0.0628(10) 0.0023(8) 0.0030(7) 0.0011(6) O3 0.0345(8) 0.0337(8) 0.0716(11) 0.0042(8) -0.0130(8) 0.0060(7) N1 0.0236(8) 0.0281(9) 0.0482(10) 0.0068(8) -0.0051(8) 0.0010(7) C1 0.0243(10) 0.0287(11) 0.0402(12) 0.0027(9) -0.0027(9) -0.0018(9) C2 0.0222(10) 0.0293(11) 0.0434(12) 0.0006(9) -0.0024(9) -0.0004(9) C3 0.0282(11) 0.0287(11) 0.0445(12) 0.0043(9) -0.0045(9) 0.0057(9) C4 0.0391(12) 0.0354(12) 0.0477(14) 0.0047(10) 0.0005(11) 0.0032(10) C5 0.054(2) 0.0484(14) 0.0472(14) 0.0064(12) 0.0039(12) 0.0116(13) C6 0.059(2) 0.058(2) 0.0472(15) -0.0075(12) -0.0126(13) 0.0117(14) C7 0.0415(14) 0.059(2) 0.056(2) -0.0069(13) -0.0128(12) -0.0028(12) C8 0.0325(12) 0.0485(13) 0.0471(14) -0.0010(11) -0.0060(10) 0.0007(10) C9 0.0228(10) 0.0341(11) 0.0478(13) 0.0026(10) 0.0025(9) 0.0032(9) C10 0.0362(12) 0.0391(12) 0.0460(13) -0.0018(10) -0.0009(10) 0.0019(10) C11 0.061(2) 0.0524(15) 0.0490(15) -0.0062(12) 0.0030(12) 0.0121(13) C12 0.081(2) 0.069(2) 0.047(2) 0.0029(14) 0.0147(14) 0.020(2) C13 0.054(2) 0.060(2) 0.063(2) 0.0217(14) 0.0244(13) 0.0182(13) C14 0.0361(12) 0.0385(12) 0.0554(14) 0.0087(11) 0.0095(11) 0.0035(10) C15 0.0325(12) 0.0275(11) 0.0412(12) -0.0019(9) -0.0045(10) 0.0017(10) C16 0.0349(11) 0.0280(11) 0.0376(11) -0.0020(9) -0.0034(9) -0.0017(9) C17 0.0421(13) 0.0314(12) 0.0550(14) 0.0039(10) -0.0031(11) 0.0019(10) C18 0.054(2) 0.0349(13) 0.069(2) 0.0112(12) -0.0005(13) -0.0118(12) C19 0.0389(13) 0.0494(15) 0.069(2) 0.0043(13) -0.0046(12) -0.0166(12) C20 0.0355(13) 0.0472(15) 0.085(2) 0.0130(13) -0.0145(13) -0.0061(11) C21 0.0366(13) 0.0356(12) 0.069(2) 0.0115(11) -0.0099(11) -0.0046(11) C22 0.0347(11) 0.0286(11) 0.0420(12) 0.0050(9) 0.0023(10) 0.0105(9) C23 0.0414(13) 0.0393(13) 0.0551(15) 0.0103(11) 0.0098(11) 0.0152(11) C24 0.065(2) 0.056(2) 0.063(2) 0.0126(14) 0.0275(15) 0.0254(14) C25 0.094(2) 0.057(2) 0.0453(15) 0.0046(14) 0.019(2) 0.035(2) C26 0.081(2) 0.0414(14) 0.0479(15) -0.0041(12) -0.0057(14) 0.0201(14) C27 0.0513(14) 0.0323(12) 0.0440(13) 0.0021(10) -0.0011(11) 0.0108(11) C28 0.0276(10) 0.0310(11) 0.0362(11) 0.0003(9) 0.0018(9) 0.0043(9) C29 0.0526(15) 0.0409(13) 0.065(2) 0.0074(12) -0.0216(13) -0.0034(12) C30 0.076(2) 0.052(2) 0.096(2) 0.023(2) -0.047(2) -0.006(2) C31 0.064(2) 0.0391(14) 0.078(2) 0.0199(13) -0.0145(15) 0.0026(13) C32 0.0414(13) 0.0337(12) 0.0532(14) 0.0032(11) 0.0083(11) -0.0008(10) C33 0.0328(11) 0.0352(12) 0.0456(13) 0.0033(10) -0.0001(10) 0.0005(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 O1 1.4923(14) . ? P1 C28 1.808(2) . ? P1 C22 1.810(2) . ? P1 C1 1.847(2) . ? O2 C9 1.445(2) . ? O3 C15 1.233(2) . ? N1 C15 1.346(2) . ? N1 C2 1.460(2) . ? C1 C9 1.569(3) . ? C1 C2 1.574(3) . ? C2 C3 1.532(3) . ? C3 C4 1.376(3) . ? C3 C8 1.388(3) . ? C4 C5 1.391(3) . ? C5 C6 1.375(3) . ? C6 C7 1.383(4) . ? C7 C8 1.377(3) . ? C9 C10 1.528(3) . ? C9 C14 1.531(3) . ? C10 C11 1.530(3) . ? C11 C12 1.514(3) . ? C12 C13 1.513(4) . ? C13 C14 1.527(3) . ? C15 C16 1.502(3) . ? C16 C17 1.382(3) . ? C16 C21 1.391(3) . ? C17 C18 1.384(3) . ? C18 C19 1.371(3) . ? C19 C20 1.383(3) . ? C20 C21 1.381(3) . ? C22 C27 1.390(3) . ? C22 C23 1.392(3) . ? C23 C24 1.385(3) . ? C24 C25 1.363(4) . ? C25 C26 1.387(4) . ? C26 C27 1.389(3) . ? C28 C29 1.386(3) . ? C28 C33 1.388(3) . ? C29 C30 1.386(3) . ? C30 C31 1.369(3) . ? C31 C32 1.365(3) . ? C32 C33 1.381(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C28 110.54(8) . . ? O1 P1 C22 111.43(9) . . ? C28 P1 C22 103.64(9) . . ? O1 P1 C1 112.06(9) . . ? C28 P1 C1 113.84(9) . . ? C22 P1 C1 104.88(9) . . ? C15 N1 C2 123.0(2) . . ? C9 C1 C2 111.0(2) . . ? C9 C1 P1 118.71(13) . . ? C2 C1 P1 110.72(13) . . ? N1 C2 C3 112.1(2) . . ? N1 C2 C1 111.72(15) . . ? C3 C2 C1 112.7(2) . . ? C4 C3 C8 118.7(2) . . ? C4 C3 C2 123.8(2) . . ? C8 C3 C2 117.4(2) . . ? C3 C4 C5 120.5(2) . . ? C6 C5 C4 120.3(2) . . ? C5 C6 C7 119.4(2) . . ? C8 C7 C6 120.1(2) . . ? C7 C8 C3 120.9(2) . . ? O2 C9 C10 105.9(2) . . ? O2 C9 C14 109.4(2) . . ? C10 C9 C14 110.2(2) . . ? O2 C9 C1 106.3(2) . . ? C10 C9 C1 112.7(2) . . ? C14 C9 C1 112.0(2) . . ? C9 C10 C11 112.7(2) . . ? C12 C11 C10 112.0(2) . . ? C13 C12 C11 110.4(2) . . ? C12 C13 C14 111.4(2) . . ? C13 C14 C9 112.0(2) . . ? O3 C15 N1 121.9(2) . . ? O3 C15 C16 122.1(2) . . ? N1 C15 C16 115.9(2) . . ? C17 C16 C21 118.1(2) . . ? C17 C16 C15 118.1(2) . . ? C21 C16 C15 123.7(2) . . ? C16 C17 C18 121.0(2) . . ? C19 C18 C17 120.5(2) . . ? C18 C19 C20 119.2(2) . . ? C21 C20 C19 120.4(2) . . ? C20 C21 C16 120.7(2) . . ? C27 C22 C23 119.4(2) . . ? C27 C22 P1 124.2(2) . . ? C23 C22 P1 116.4(2) . . ? C24 C23 C22 120.2(2) . . ? C25 C24 C23 120.3(3) . . ? C24 C25 C26 120.3(2) . . ? C25 C26 C27 120.0(3) . . ? C26 C27 C22 119.7(2) . . ? C29 C28 C33 119.0(2) . . ? C29 C28 P1 115.9(2) . . ? C33 C28 P1 124.77(15) . . ? C28 C29 C30 119.9(2) . . ? C31 C30 C29 120.5(2) . . ? C32 C31 C30 120.1(2) . . ? C31 C32 C33 120.4(2) . . ? C32 C33 C28 120.2(2) . . ? _refine_diff_density_max 0.230 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.056