# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Alex Ionkin' _publ_contact_author_email ALEX.S.IONKIN@USA.DUPONT.COM _publ_section_title ; A Stable Enol In Small Ring Systems: Clear Differentiation Between Penta- and Tri-valency Of Phosphorus Atoms. ; loop_ _publ_author_name 'Alex Ionkin' 'Brian M. Fish' 'William J. Marshall' 'Charles N. McEwen' 'Matthew F. Schiffhauer' # Attachment 'Enol.cif' data_06213 _database_code_depnum_ccdc_archive 'CCDC 691153' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H21 O2 P' _chemical_formula_weight 216.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.1970(4) _cell_length_b 8.5935(5) _cell_length_c 11.9624(7) _cell_angle_alpha 79.0472(10) _cell_angle_beta 85.1087(11) _cell_angle_gamma 80.2040(10) _cell_volume 615.40(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelpiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.520 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.320 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.167 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 236 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 26437 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0131 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 30.72 _reflns_number_total 3801 _reflns_number_gt 3479 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0475P)^2^+0.1197P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3801 _refine_ls_number_parameters 143 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0322 _refine_ls_R_factor_gt 0.0288 _refine_ls_wR_factor_ref 0.0859 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.22262(3) 0.11085(2) 0.412652(17) 0.02163(7) Uani 1 1 d . . . O1 O 0.21560(13) -0.06421(8) 0.42089(6) 0.03341(16) Uani 1 1 d . . . O2 O -0.20177(10) 0.30779(8) 0.41511(6) 0.02502(13) Uani 1 1 d . . . C1 C 0.00509(13) 0.27056(9) 0.37440(6) 0.01904(14) Uani 1 1 d . . . C2 C 0.13894(12) 0.35841(9) 0.30164(6) 0.01817(14) Uani 1 1 d . . . C3 C 0.35013(13) 0.23611(9) 0.29175(7) 0.02029(14) Uani 1 1 d . . . H3A H 0.4762 0.2744 0.3155 0.024 Uiso 1 1 calc R . . C4 C 0.10549(13) 0.53823(9) 0.25685(7) 0.02088(15) Uani 1 1 d . . . C5 C 0.32562(17) 0.59969(11) 0.24775(10) 0.0351(2) Uani 1 1 d . . . H5A H 0.4236 0.5498 0.1937 0.053 Uiso 1 1 calc R . . H5B H 0.3882 0.5738 0.3210 0.053 Uiso 1 1 calc R . . H5C H 0.3029 0.7140 0.2229 0.053 Uiso 1 1 calc R . . C6 C -0.05080(16) 0.62701(10) 0.33921(8) 0.02905(18) Uani 1 1 d . . . H6A H 0.0044 0.5989 0.4142 0.044 Uiso 1 1 calc R . . H6B H -0.1935 0.5968 0.3415 0.044 Uiso 1 1 calc R . . H6C H -0.0609 0.7407 0.3135 0.044 Uiso 1 1 calc R . . C7 C 0.00464(19) 0.57732(12) 0.13994(8) 0.0335(2) Uani 1 1 d . . . H7A H 0.1016 0.5254 0.0864 0.050 Uiso 1 1 calc R . . H7B H -0.0168 0.6913 0.1137 0.050 Uiso 1 1 calc R . . H7C H -0.1340 0.5397 0.1466 0.050 Uiso 1 1 calc R . . C8 C 0.41341(14) 0.15907(10) 0.18373(7) 0.02444(16) Uani 1 1 d . . . C9 C 0.59015(16) 0.01170(12) 0.21592(9) 0.0329(2) Uani 1 1 d . . . H9A H 0.6424 -0.0330 0.1491 0.049 Uiso 1 1 calc R . . H9B H 0.5284 -0.0673 0.2714 0.049 Uiso 1 1 calc R . . H9C H 0.7099 0.0434 0.2474 0.049 Uiso 1 1 calc R . . C10 C 0.5146(2) 0.27601(13) 0.08883(9) 0.0397(2) Uani 1 1 d . . . H10A H 0.5648 0.2234 0.0253 0.060 Uiso 1 1 calc R . . H10B H 0.6362 0.3101 0.1169 0.060 Uiso 1 1 calc R . . H10C H 0.4062 0.3678 0.0649 0.060 Uiso 1 1 calc R . . C11 C 0.21608(17) 0.10851(12) 0.13986(8) 0.03173(19) Uani 1 1 d . . . H11A H 0.2626 0.0576 0.0752 0.048 Uiso 1 1 calc R . . H11B H 0.1085 0.2015 0.1178 0.048 Uiso 1 1 calc R . . H11C H 0.1533 0.0347 0.1990 0.048 Uiso 1 1 calc R . . H1 H 0.295(2) 0.1369(16) 0.5035(11) 0.034(3) Uiso 1 1 d . . . H2 H -0.224(2) 0.2347(19) 0.4670(14) 0.046(4) 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 0.02596(11) 0.01749(11) 0.01851(11) 0.00105(7) -0.00038(7) -0.00040(7) O1 0.0451(4) 0.0172(3) 0.0321(3) 0.0017(2) 0.0117(3) -0.0022(3) O2 0.0211(3) 0.0232(3) 0.0273(3) 0.0026(2) 0.0016(2) -0.0032(2) C1 0.0212(3) 0.0172(3) 0.0185(3) -0.0014(3) -0.0024(3) -0.0039(3) C2 0.0208(3) 0.0162(3) 0.0176(3) -0.0016(2) -0.0030(2) -0.0038(2) C3 0.0199(3) 0.0178(3) 0.0224(3) -0.0013(3) -0.0012(3) -0.0032(3) C4 0.0251(4) 0.0158(3) 0.0209(3) -0.0001(3) -0.0026(3) -0.0040(3) C5 0.0322(5) 0.0215(4) 0.0522(6) -0.0024(4) -0.0008(4) -0.0115(3) C6 0.0383(5) 0.0182(4) 0.0285(4) -0.0035(3) 0.0012(3) -0.0008(3) C7 0.0460(5) 0.0286(4) 0.0228(4) 0.0023(3) -0.0087(4) -0.0013(4) C8 0.0271(4) 0.0203(4) 0.0235(4) -0.0018(3) 0.0049(3) -0.0025(3) C9 0.0306(4) 0.0258(4) 0.0378(5) -0.0038(4) 0.0067(4) 0.0025(3) C10 0.0483(6) 0.0293(5) 0.0349(5) 0.0006(4) 0.0188(4) -0.0052(4) C11 0.0385(5) 0.0320(5) 0.0263(4) -0.0103(3) -0.0022(3) -0.0038(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 O1 1.4966(7) . ? P1 C1 1.7741(8) . ? P1 C3 1.8379(8) . ? P1 C2 2.2862(8) . ? P1 H1 1.282(13) . ? O2 C1 1.3401(10) . ? O2 H2 0.816(16) . ? C1 C2 1.3623(10) . ? C2 C4 1.5210(11) . ? C2 C3 1.5441(11) . ? C3 C8 1.5531(12) . ? C3 H3A 0.9800 . ? C4 C5 1.5329(12) . ? C4 C7 1.5357(12) . ? C4 C6 1.5370(12) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C11 1.5285(13) . ? C8 C10 1.5335(13) . ? C8 C9 1.5383(12) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 C1 126.24(4) . . ? O1 P1 C3 124.57(4) . . ? C1 P1 C3 78.03(4) . . ? O1 P1 C2 144.10(4) . . ? C1 P1 C2 36.53(3) . . ? C3 P1 C2 42.25(3) . . ? O1 P1 H1 110.5(6) . . ? C1 P1 H1 105.8(6) . . ? C3 P1 H1 106.9(6) . . ? C2 P1 H1 105.3(6) . . ? C1 O2 H2 106.6(11) . . ? O2 C1 C2 131.88(7) . . ? O2 C1 P1 134.45(6) . . ? C2 C1 P1 92.65(5) . . ? C1 C2 C4 128.77(7) . . ? C1 C2 C3 102.81(6) . . ? C4 C2 C3 127.70(7) . . ? C1 C2 P1 50.82(4) . . ? C4 C2 P1 163.60(6) . . ? C3 C2 P1 53.16(4) . . ? C2 C3 C8 121.95(7) . . ? C2 C3 P1 84.59(5) . . ? C8 C3 P1 115.55(6) . . ? C2 C3 H3A 110.7 . . ? C8 C3 H3A 110.7 . . ? P1 C3 H3A 110.7 . . ? C2 C4 C5 109.69(7) . . ? C2 C4 C7 110.82(7) . . ? C5 C4 C7 110.01(8) . . ? C2 C4 C6 110.24(7) . . ? C5 C4 C6 108.02(7) . . ? C7 C4 C6 108.01(7) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C11 C8 C10 109.42(8) . . ? C11 C8 C9 109.98(8) . . ? C10 C8 C9 107.50(8) . . ? C11 C8 C3 111.88(7) . . ? C10 C8 C3 110.47(7) . . ? C9 C8 C3 107.47(7) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C8 C10 H10A 109.5 . . ? C8 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C8 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C8 C11 H11A 109.5 . . ? C8 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C8 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 P1 C1 O2 56.79(10) . . . . ? C3 P1 C1 O2 -178.90(9) . . . . ? C2 P1 C1 O2 -168.96(11) . . . . ? O1 P1 C1 C2 -134.26(5) . . . . ? C3 P1 C1 C2 -9.94(5) . . . . ? O2 C1 C2 C4 10.55(14) . . . . ? P1 C1 C2 C4 -158.87(7) . . . . ? O2 C1 C2 C3 -178.69(8) . . . . ? P1 C1 C2 C3 11.90(6) . . . . ? O2 C1 C2 P1 169.42(11) . . . . ? O1 P1 C2 C1 80.14(8) . . . . ? C3 P1 C2 C1 165.45(7) . . . . ? O1 P1 C2 C4 175.41(18) . . . . ? C1 P1 C2 C4 95.3(2) . . . . ? C3 P1 C2 C4 -99.3(2) . . . . ? O1 P1 C2 C3 -85.32(7) . . . . ? C1 P1 C2 C3 -165.45(7) . . . . ? C1 C2 C3 C8 105.33(8) . . . . ? C4 C2 C3 C8 -83.78(10) . . . . ? P1 C2 C3 C8 116.84(8) . . . . ? C1 C2 C3 P1 -11.52(6) . . . . ? C4 C2 C3 P1 159.38(7) . . . . ? O1 P1 C3 C2 134.79(5) . . . . ? C1 P1 C3 C2 8.79(4) . . . . ? O1 P1 C3 C8 11.83(8) . . . . ? C1 P1 C3 C8 -114.16(6) . . . . ? C2 P1 C3 C8 -122.95(8) . . . . ? C1 C2 C4 C5 142.87(9) . . . . ? C3 C2 C4 C5 -25.72(11) . . . . ? P1 C2 C4 C5 61.0(2) . . . . ? C1 C2 C4 C7 -95.47(10) . . . . ? C3 C2 C4 C7 95.94(10) . . . . ? P1 C2 C4 C7 -177.36(17) . . . . ? C1 C2 C4 C6 24.05(11) . . . . ? C3 C2 C4 C6 -144.54(8) . . . . ? P1 C2 C4 C6 -57.8(2) . . . . ? C2 C3 C8 C11 -43.09(10) . . . . ? P1 C3 C8 C11 56.99(9) . . . . ? C2 C3 C8 C10 79.08(10) . . . . ? P1 C3 C8 C10 179.16(7) . . . . ? C2 C3 C8 C9 -163.92(7) . . . . ? P1 C3 C8 C9 -63.84(8) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.72 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.421 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.044 data_06210 _database_code_depnum_ccdc_archive 'CCDC 691154' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H56 O2 P2 Si2' _chemical_formula_weight 542.85 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Si Si 0.0817 0.0704 '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' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+5/6' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+7/6' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z-1/6' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+1/6' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' _cell_length_a 17.1720(18) _cell_length_b 17.1720(18) _cell_length_c 60.643(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 15486(3) _cell_formula_units_Z 18 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ireg.blok _exptl_crystal_colour colourless _exptl_crystal_size_min 0.480 _exptl_crystal_size_mid 0.480 _exptl_crystal_size_max 0.500 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.048 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 5364 _exptl_absorpt_coefficient_mu 0.216 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 55549 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0191 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -77 _diffrn_reflns_limit_l_max 78 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 27.25 _reflns_number_total 3863 _reflns_number_gt 3183 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+28.5907P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3863 _refine_ls_number_parameters 167 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0624 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1418 _refine_ls_wR_factor_gt 0.1232 _refine_ls_goodness_of_fit_ref 1.091 _refine_ls_restrained_S_all 1.091 _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 Si1 Si 0.42496(4) 0.91343(5) 0.118599(12) 0.0549(2) Uani 1 1 d . . . C1 C 0.60047(12) 0.99722(12) 0.10442(3) 0.0331(4) Uani 1 1 d . . . O1 O 0.52050(9) 0.99535(9) 0.10832(2) 0.0415(3) Uani 1 1 d . . . P1 P 0.59381(3) 0.91096(3) 0.085298(7) 0.03364(15) Uani 1 1 d . . . C2 C 0.67878(13) 1.05823(12) 0.11338(3) 0.0338(4) Uani 1 1 d . . . C3 C 0.75847(13) 1.04434(13) 0.10862(3) 0.0343(4) Uani 1 1 d . . . C4 C 0.4493(3) 0.8523(3) 0.14034(6) 0.1002(12) Uani 1 1 d . . . H4A H 0.4786 0.8227 0.1338 0.150 Uiso 1 1 calc R . . H4B H 0.3941 0.8085 0.1471 0.150 Uiso 1 1 calc R . . H4C H 0.4880 0.8943 0.1513 0.150 Uiso 1 1 calc R . . C5 C 0.3682(2) 0.9707(2) 0.13045(7) 0.0929(12) Uani 1 1 d . . . H5A H 0.3557 1.0014 0.1190 0.139 Uiso 1 1 calc R . . H5B H 0.4065 1.0135 0.1413 0.139 Uiso 1 1 calc R . . H5C H 0.3129 0.9272 0.1373 0.139 Uiso 1 1 calc R . . C6 C 0.3561(2) 0.8353(3) 0.09676(6) 0.1033(14) Uani 1 1 d . . . H6A H 0.3539 0.8687 0.0843 0.155 Uiso 1 1 calc R . . H6B H 0.2962 0.7968 0.1022 0.155 Uiso 1 1 calc R . . H6C H 0.3820 0.7994 0.0924 0.155 Uiso 1 1 calc R . . C7 C 0.68872(14) 1.14047(14) 0.12654(3) 0.0441(5) Uani 1 1 d . . . C8 C 0.6450(2) 1.18602(18) 0.11394(5) 0.0675(7) Uani 1 1 d . . . H8A H 0.6767 1.2102 0.1004 0.101 Uiso 1 1 calc R . . H8B H 0.6476 1.2337 0.1227 0.101 Uiso 1 1 calc R . . H8C H 0.5834 1.1427 0.1108 0.101 Uiso 1 1 calc R . . C9 C 0.64392(18) 1.11286(18) 0.14945(4) 0.0648(7) Uani 1 1 d . . . H9A H 0.6492 1.1647 0.1568 0.097 Uiso 1 1 calc R . . H9B H 0.6732 1.0880 0.1580 0.097 Uiso 1 1 calc R . . H9C H 0.5815 1.0687 0.1477 0.097 Uiso 1 1 calc R . . C10 C 0.78798(16) 1.21387(15) 0.12919(4) 0.0531(5) Uani 1 1 d . . . H10A H 0.8156 1.2314 0.1149 0.080 Uiso 1 1 calc R . . H10B H 0.8189 1.1908 0.1378 0.080 Uiso 1 1 calc R . . H10C H 0.7914 1.2651 0.1365 0.080 Uiso 1 1 calc R . . C11 C 0.78137(15) 0.99120(15) 0.12645(3) 0.0437(5) Uani 1 1 d . . . C12 C 0.8035(3) 1.0362(3) 0.14868(4) 0.0934(12) Uani 1 1 d . . . H12A H 0.8157 1.0010 0.1589 0.140 Uiso 1 1 calc R . . H12B H 0.7534 1.0413 0.1539 0.140 Uiso 1 1 calc R . . H12C H 0.8554 1.0951 0.1474 0.140 Uiso 1 1 calc R . . C13 C 0.8661(3) 0.9902(3) 0.11935(5) 0.0957(12) Uani 1 1 d . . . H13A H 0.8822 0.9610 0.1305 0.144 Uiso 1 1 calc R . . H13B H 0.9143 1.0508 0.1174 0.144 Uiso 1 1 calc R . . H13C H 0.8550 0.9581 0.1057 0.144 Uiso 1 1 calc R . . C14 C 0.7067(2) 0.8963(2) 0.12902(6) 0.1033(14) Uani 1 1 d . . . H14A H 0.7231 0.8664 0.1399 0.155 Uiso 1 1 calc R . . H14B H 0.6958 0.8656 0.1152 0.155 Uiso 1 1 calc R . . H14C H 0.6531 0.8961 0.1337 0.155 Uiso 1 1 calc R . . H3 H 0.8126(15) 1.1010(15) 0.1062(4) 0.039(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 Si1 0.0383(3) 0.0510(4) 0.0592(4) -0.0099(3) 0.0108(3) 0.0102(3) C1 0.0353(9) 0.0327(9) 0.0284(8) -0.0007(7) 0.0014(7) 0.0149(7) O1 0.0322(7) 0.0430(8) 0.0449(7) -0.0045(6) 0.0027(6) 0.0153(6) P1 0.0407(3) 0.0305(2) 0.0264(2) -0.00168(17) -0.00341(17) 0.0153(2) C2 0.0387(9) 0.0345(9) 0.0258(8) -0.0023(7) 0.0011(7) 0.0166(8) C3 0.0377(10) 0.0382(10) 0.0261(8) -0.0028(7) -0.0037(7) 0.0183(8) C4 0.088(2) 0.098(3) 0.095(2) 0.044(2) 0.032(2) 0.032(2) C5 0.0521(16) 0.083(2) 0.129(3) -0.024(2) 0.0299(18) 0.0225(15) C6 0.0471(16) 0.103(3) 0.105(3) -0.046(2) 0.0066(16) -0.0035(16) C7 0.0459(11) 0.0398(10) 0.0421(10) -0.0125(8) -0.0009(8) 0.0181(9) C8 0.0716(17) 0.0489(13) 0.091(2) -0.0202(13) -0.0156(15) 0.0367(13) C9 0.0614(15) 0.0646(15) 0.0501(13) -0.0217(12) 0.0136(11) 0.0178(12) C10 0.0516(13) 0.0400(11) 0.0569(13) -0.0149(10) -0.0018(10) 0.0148(10) C11 0.0519(12) 0.0529(12) 0.0308(9) -0.0011(8) -0.0102(8) 0.0296(10) C12 0.167(4) 0.109(3) 0.0384(13) -0.0170(15) -0.0383(18) 0.094(3) C13 0.111(3) 0.172(4) 0.0599(17) 0.025(2) 0.0005(17) 0.113(3) C14 0.098(2) 0.0635(18) 0.113(3) 0.0390(18) -0.053(2) 0.0139(17) _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 Si1 O1 1.6589(15) . ? Si1 C6 1.835(3) . ? Si1 C5 1.842(3) . ? Si1 C4 1.858(4) . ? C1 C2 1.339(3) . ? C1 O1 1.378(2) . ? C1 P1 1.8391(18) . ? P1 C3 1.8918(18) 18_654 ? P1 P1 2.1802(10) 18_654 ? C2 C3 1.529(3) . ? C2 C7 1.556(3) . ? C3 C11 1.586(3) . ? C3 P1 1.8918(18) 18_654 ? C7 C8 1.531(3) . ? C7 C10 1.540(3) . ? C7 C9 1.543(3) . ? C11 C14 1.495(4) . ? C11 C12 1.505(3) . ? C11 C13 1.525(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Si1 C6 110.58(12) . . ? O1 Si1 C5 104.87(12) . . ? C6 Si1 C5 110.65(18) . . ? O1 Si1 C4 109.81(13) . . ? C6 Si1 C4 110.1(2) . . ? C5 Si1 C4 110.70(19) . . ? C2 C1 O1 123.24(16) . . ? C2 C1 P1 121.32(14) . . ? O1 C1 P1 115.43(13) . . ? C1 O1 Si1 129.48(13) . . ? C1 P1 C3 101.55(8) . 18_654 ? C1 P1 P1 90.88(6) . 18_654 ? C3 P1 P1 93.02(6) 18_654 18_654 ? C1 C2 C3 115.37(16) . . ? C1 C2 C7 122.01(17) . . ? C3 C2 C7 122.53(16) . . ? C2 C3 C11 117.36(16) . . ? C2 C3 P1 109.20(12) . 18_654 ? C11 C3 P1 107.67(13) . 18_654 ? C8 C7 C10 105.0(2) . . ? C8 C7 C9 108.0(2) . . ? C10 C7 C9 109.59(18) . . ? C8 C7 C2 110.37(17) . . ? C10 C7 C2 111.76(17) . . ? C9 C7 C2 111.81(18) . . ? C14 C11 C12 109.0(3) . . ? C14 C11 C13 108.7(3) . . ? C12 C11 C13 105.2(2) . . ? C14 C11 C3 111.95(18) . . ? C12 C11 C3 112.75(19) . . ? C13 C11 C3 109.03(18) . . ? 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 C2 C1 O1 Si1 -122.12(18) . . . . ? P1 C1 O1 Si1 59.30(19) . . . . ? C6 Si1 O1 C1 -85.3(2) . . . . ? C5 Si1 O1 C1 155.4(2) . . . . ? C4 Si1 O1 C1 36.5(2) . . . . ? C2 C1 P1 C3 -107.38(16) . . . 18_654 ? O1 C1 P1 C3 71.22(15) . . . 18_654 ? C2 C1 P1 P1 -14.12(15) . . . 18_654 ? O1 C1 P1 P1 164.48(13) . . . 18_654 ? O1 C1 C2 C3 175.03(16) . . . . ? P1 C1 C2 C3 -6.5(2) . . . . ? O1 C1 C2 C7 -8.4(3) . . . . ? P1 C1 C2 C7 170.12(14) . . . . ? C1 C2 C3 C11 -95.0(2) . . . . ? C7 C2 C3 C11 88.4(2) . . . . ? C1 C2 C3 P1 27.8(2) . . . 18_654 ? C7 C2 C3 P1 -148.78(15) . . . 18_654 ? C1 C2 C7 C8 -46.8(3) . . . . ? C3 C2 C7 C8 129.5(2) . . . . ? C1 C2 C7 C10 -163.23(19) . . . . ? C3 C2 C7 C10 13.1(3) . . . . ? C1 C2 C7 C9 73.5(3) . . . . ? C3 C2 C7 C9 -110.1(2) . . . . ? C2 C3 C11 C14 63.4(3) . . . . ? P1 C3 C11 C14 -60.2(3) 18_654 . . . ? C2 C3 C11 C12 -59.9(3) . . . . ? P1 C3 C11 C12 176.5(2) 18_654 . . . ? C2 C3 C11 C13 -176.3(2) . . . . ? P1 C3 C11 C13 60.1(2) 18_654 . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.25 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.534 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.054 #===END data_06027 _database_code_depnum_ccdc_archive 'CCDC 691155' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H39 O2 P' _chemical_formula_weight 366.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 11.3952(6) _cell_length_b 11.9039(6) _cell_length_c 33.5993(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4557.7(4) _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 iregblok _exptl_crystal_colour yellow _exptl_crystal_size_min 0.370 _exptl_crystal_size_mid 0.370 _exptl_crystal_size_max 0.420 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.068 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 78472 _diffrn_reflns_av_R_equivalents 0.0417 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -44 _diffrn_reflns_limit_l_max 44 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.27 _reflns_number_total 5626 _reflns_number_gt 4542 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0730P)^2^+1.8779P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5626 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0639 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1426 _refine_ls_wR_factor_gt 0.1330 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.073 _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 0.04871(4) 0.03100(3) 0.369285(11) 0.02853(12) Uani 1 1 d . . . O1 O 0.13060(12) -0.04952(11) 0.44464(4) 0.0446(3) Uani 1 1 d . . . C1 C 0.14756(15) -0.01487(12) 0.41175(5) 0.0316(3) Uani 1 1 d . . . O2 O 0.05264(10) 0.25827(9) 0.37447(3) 0.0341(3) Uani 1 1 d . . . C4 C -0.00594(13) 0.17689(12) 0.38298(4) 0.0264(3) Uani 1 1 d . . . C3 C 0.20202(13) 0.05684(12) 0.35081(4) 0.0268(3) Uani 1 1 d . . . H3A H 0.2172 0.1378 0.3498 0.032 Uiso 1 1 calc R . . C2 C 0.26130(15) 0.00543(13) 0.38858(4) 0.0300(3) Uani 1 1 d . . . H2A H 0.2969 -0.0670 0.3817 0.036 Uiso 1 1 calc R . . C5 C 0.22636(15) 0.00390(14) 0.30930(4) 0.0321(3) Uani 1 1 d . . . C6 C 0.14624(18) 0.06280(17) 0.27946(5) 0.0434(4) Uani 1 1 d . . . H6A H 0.1619 0.0348 0.2532 0.065 Uiso 1 1 calc R . . H6B H 0.1607 0.1422 0.2802 0.065 Uiso 1 1 calc R . . H6C H 0.0658 0.0484 0.2862 0.065 Uiso 1 1 calc R . . C7 C 0.2018(2) -0.12231(16) 0.30890(6) 0.0490(5) Uani 1 1 d . . . H7A H 0.2171 -0.1517 0.2828 0.073 Uiso 1 1 calc R . . H7B H 0.1212 -0.1354 0.3158 0.073 Uiso 1 1 calc R . . H7C H 0.2517 -0.1590 0.3279 0.073 Uiso 1 1 calc R . . C8 C 0.35358(18) 0.0237(2) 0.29672(6) 0.0501(5) Uani 1 1 d . . . H8A H 0.3652 -0.0043 0.2702 0.075 Uiso 1 1 calc R . . H8B H 0.4052 -0.0148 0.3147 0.075 Uiso 1 1 calc R . . H8C H 0.3703 0.1028 0.2973 0.075 Uiso 1 1 calc R . . C9 C 0.35134(15) 0.07716(14) 0.41262(5) 0.0340(4) Uani 1 1 d . . . C10 C 0.29240(19) 0.17898(16) 0.43193(6) 0.0479(5) Uani 1 1 d . . . H10A H 0.3510 0.2254 0.4442 0.072 Uiso 1 1 calc R . . H10B H 0.2376 0.1539 0.4517 0.072 Uiso 1 1 calc R . . H10C H 0.2517 0.2215 0.4120 0.072 Uiso 1 1 calc R . . C11 C 0.4049(2) 0.0031(2) 0.44516(6) 0.0569(5) Uani 1 1 d . . . H11A H 0.4597 0.0464 0.4605 0.085 Uiso 1 1 calc R . . H11B H 0.4448 -0.0593 0.4331 0.085 Uiso 1 1 calc R . . H11C H 0.3437 -0.0243 0.4623 0.085 Uiso 1 1 calc R . . C12 C 0.44870(18) 0.1195(2) 0.38570(7) 0.0573(6) Uani 1 1 d . . . H12A H 0.5018 0.1652 0.4009 0.086 Uiso 1 1 calc R . . H12B H 0.4154 0.1634 0.3645 0.086 Uiso 1 1 calc R . . H12C H 0.4904 0.0567 0.3747 0.086 Uiso 1 1 calc R . . C13 C -0.21335(15) 0.23243(14) 0.37733(5) 0.0327(3) Uani 1 1 d . . . H13A H -0.2846 0.2397 0.3906 0.039 Uiso 1 1 calc R . . C14 C -0.12803(13) 0.18818(13) 0.39978(4) 0.0273(3) Uani 1 1 d . . . C15 C -0.21695(15) 0.27315(14) 0.33450(5) 0.0331(3) Uani 1 1 d . . . C16 C -0.13532(17) 0.21189(19) 0.30588(5) 0.0462(5) Uani 1 1 d . . . H16A H -0.0559 0.2352 0.3106 0.069 Uiso 1 1 calc R . . H16B H -0.1568 0.2296 0.2790 0.069 Uiso 1 1 calc R . . H16C H -0.1418 0.1323 0.3100 0.069 Uiso 1 1 calc R . . C17 C -0.34355(17) 0.2536(2) 0.31946(6) 0.0506(5) Uani 1 1 d . . . H17A H -0.3978 0.2915 0.3367 0.076 Uiso 1 1 calc R . . H17B H -0.3603 0.1746 0.3194 0.076 Uiso 1 1 calc R . . H17C H -0.3511 0.2827 0.2929 0.076 Uiso 1 1 calc R . . C18 C -0.1927(2) 0.39900(16) 0.33419(6) 0.0528(5) Uani 1 1 d . . . H18A H -0.1142 0.4126 0.3434 0.079 Uiso 1 1 calc R . . H18B H -0.2475 0.4364 0.3514 0.079 Uiso 1 1 calc R . . H18C H -0.2009 0.4273 0.3076 0.079 Uiso 1 1 calc R . . C19 C -0.14679(14) 0.15062(13) 0.44321(4) 0.0290(3) Uani 1 1 d . . . C20 C -0.25777(17) 0.20196(16) 0.46143(5) 0.0409(4) Uani 1 1 d . . . H20A H -0.2627 0.1817 0.4890 0.061 Uiso 1 1 calc R . . H20B H -0.3255 0.1741 0.4476 0.061 Uiso 1 1 calc R . . H20C H -0.2546 0.2823 0.4590 0.061 Uiso 1 1 calc R . . C21 C -0.15812(18) 0.02252(14) 0.44519(5) 0.0405(4) Uani 1 1 d . . . H21A H -0.1659 -0.0005 0.4724 0.061 Uiso 1 1 calc R . . H21B H -0.0894 -0.0115 0.4338 0.061 Uiso 1 1 calc R . . H21C H -0.2262 -0.0008 0.4305 0.061 Uiso 1 1 calc R . . C22 C -0.04165(16) 0.18864(15) 0.46834(5) 0.0364(4) Uani 1 1 d . . . H22A H -0.0524 0.1646 0.4954 0.055 Uiso 1 1 calc R . . H22B H -0.0357 0.2691 0.4675 0.055 Uiso 1 1 calc R . . H22C H 0.0289 0.1561 0.4579 0.055 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 0.0350(2) 0.0249(2) 0.0257(2) -0.00139(14) 0.00282(15) -0.00303(15) O1 0.0591(8) 0.0430(7) 0.0317(6) 0.0125(5) 0.0074(6) 0.0033(6) C1 0.0453(9) 0.0216(7) 0.0278(7) 0.0011(5) 0.0041(7) 0.0006(6) O2 0.0345(6) 0.0269(5) 0.0408(6) 0.0033(5) 0.0068(5) -0.0029(4) C4 0.0315(7) 0.0274(7) 0.0202(6) 0.0003(5) 0.0004(5) -0.0002(6) C3 0.0350(8) 0.0241(7) 0.0213(7) 0.0000(5) 0.0028(6) -0.0004(6) C2 0.0377(8) 0.0264(7) 0.0258(7) 0.0012(6) 0.0017(6) 0.0040(6) C5 0.0409(9) 0.0340(8) 0.0212(7) -0.0021(6) 0.0044(6) 0.0042(7) C6 0.0549(11) 0.0518(10) 0.0235(8) -0.0027(7) 0.0007(7) 0.0106(9) C7 0.0735(14) 0.0359(9) 0.0376(9) -0.0119(7) 0.0045(9) 0.0045(9) C8 0.0466(11) 0.0684(13) 0.0351(9) -0.0030(9) 0.0137(8) 0.0086(9) C9 0.0357(8) 0.0359(8) 0.0302(8) 0.0016(6) -0.0049(6) 0.0015(7) C10 0.0533(11) 0.0390(9) 0.0514(11) -0.0125(8) -0.0137(9) -0.0004(8) C11 0.0665(14) 0.0578(12) 0.0465(11) 0.0109(9) -0.0205(10) 0.0084(11) C12 0.0376(10) 0.0834(16) 0.0508(12) 0.0057(11) -0.0051(8) -0.0129(10) C13 0.0340(8) 0.0365(8) 0.0278(8) 0.0027(6) 0.0048(6) -0.0003(6) C14 0.0337(8) 0.0270(7) 0.0213(7) 0.0006(5) 0.0043(5) -0.0040(6) C15 0.0375(8) 0.0382(8) 0.0237(7) 0.0048(6) 0.0016(6) 0.0008(7) C16 0.0493(10) 0.0657(13) 0.0235(8) 0.0036(8) 0.0023(7) 0.0128(9) C17 0.0429(10) 0.0705(14) 0.0384(10) 0.0061(9) -0.0067(8) 0.0025(10) C18 0.0799(15) 0.0404(10) 0.0381(10) 0.0103(8) 0.0039(10) -0.0067(10) C19 0.0359(8) 0.0301(7) 0.0209(7) 0.0031(6) 0.0047(6) -0.0023(6) C20 0.0432(9) 0.0503(10) 0.0293(8) 0.0019(7) 0.0091(7) 0.0050(8) C21 0.0586(11) 0.0317(8) 0.0313(8) 0.0047(6) 0.0094(8) -0.0094(8) C22 0.0435(9) 0.0432(9) 0.0226(7) 0.0022(6) 0.0009(6) -0.0053(7) _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 C3 1.8794(16) . ? P1 C1 1.8982(17) . ? P1 C4 1.9014(15) . ? O1 C1 1.1951(19) . ? C1 C2 1.531(2) . ? O2 C4 1.2107(18) . ? C4 C14 1.507(2) . ? C3 C5 1.555(2) . ? C3 C2 1.563(2) . ? C2 C9 1.560(2) . ? C5 C6 1.526(2) . ? C5 C7 1.528(2) . ? C5 C8 1.528(3) . ? C9 C12 1.517(3) . ? C9 C10 1.530(2) . ? C9 C11 1.531(2) . ? C13 C14 1.339(2) . ? C13 C15 1.519(2) . ? C14 C19 1.541(2) . ? C15 C18 1.524(3) . ? C15 C16 1.524(2) . ? C15 C17 1.546(3) . ? C19 C21 1.532(2) . ? C19 C20 1.532(2) . ? C19 C22 1.534(2) . ? 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 C3 P1 C1 75.15(7) . . ? C3 P1 C4 103.59(7) . . ? C1 P1 C4 105.97(7) . . ? O1 C1 C2 131.41(16) . . ? O1 C1 P1 134.29(14) . . ? C2 C1 P1 94.28(10) . . ? O2 C4 C14 121.73(13) . . ? O2 C4 P1 119.55(12) . . ? C14 C4 P1 118.32(10) . . ? C5 C3 C2 119.51(13) . . ? C5 C3 P1 113.31(11) . . ? C2 C3 P1 93.98(9) . . ? C1 C2 C9 112.32(12) . . ? C1 C2 C3 96.26(12) . . ? C9 C2 C3 119.37(13) . . ? C6 C5 C7 109.65(15) . . ? C6 C5 C8 108.35(15) . . ? C7 C5 C8 108.86(16) . . ? C6 C5 C3 107.23(13) . . ? C7 C5 C3 111.92(13) . . ? C8 C5 C3 110.76(14) . . ? C12 C9 C10 108.09(17) . . ? C12 C9 C11 109.00(17) . . ? C10 C9 C11 109.15(16) . . ? C12 C9 C2 110.74(14) . . ? C10 C9 C2 111.37(14) . . ? C11 C9 C2 108.45(15) . . ? C14 C13 C15 132.77(15) . . ? C13 C14 C4 119.63(13) . . ? C13 C14 C19 123.16(14) . . ? C4 C14 C19 117.18(13) . . ? C13 C15 C18 108.38(14) . . ? C13 C15 C16 115.38(14) . . ? C18 C15 C16 110.82(16) . . ? C13 C15 C17 106.67(14) . . ? C18 C15 C17 108.37(16) . . ? C16 C15 C17 106.95(15) . . ? C21 C19 C20 108.07(14) . . ? C21 C19 C22 109.62(14) . . ? C20 C19 C22 107.89(13) . . ? C21 C19 C14 109.97(13) . . ? C20 C19 C14 112.14(13) . . ? C22 C19 C14 109.10(12) . . ? 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 C3 P1 C1 O1 177.30(19) . . . . ? C4 P1 C1 O1 77.11(18) . . . . ? C3 P1 C1 C2 -4.03(9) . . . . ? C4 P1 C1 C2 -104.22(10) . . . . ? C3 P1 C4 O2 8.05(14) . . . . ? C1 P1 C4 O2 86.22(13) . . . . ? C3 P1 C4 C14 -179.16(11) . . . . ? C1 P1 C4 C14 -100.99(12) . . . . ? C1 P1 C3 C5 128.54(12) . . . . ? C4 P1 C3 C5 -128.24(11) . . . . ? C1 P1 C3 C2 3.95(9) . . . . ? C4 P1 C3 C2 107.18(9) . . . . ? O1 C1 C2 C9 -51.2(2) . . . . ? P1 C1 C2 C9 130.05(11) . . . . ? O1 C1 C2 C3 -176.55(17) . . . . ? P1 C1 C2 C3 4.72(10) . . . . ? C5 C3 C2 C1 -124.45(14) . . . . ? P1 C3 C2 C1 -4.77(10) . . . . ? C5 C3 C2 C9 115.54(16) . . . . ? P1 C3 C2 C9 -124.77(13) . . . . ? C2 C3 C5 C6 173.56(14) . . . . ? P1 C3 C5 C6 64.25(15) . . . . ? C2 C3 C5 C7 53.3(2) . . . . ? P1 C3 C5 C7 -56.03(17) . . . . ? C2 C3 C5 C8 -68.40(19) . . . . ? P1 C3 C5 C8 -177.72(12) . . . . ? C1 C2 C9 C12 -166.11(15) . . . . ? C3 C2 C9 C12 -54.6(2) . . . . ? C1 C2 C9 C10 -45.80(18) . . . . ? C3 C2 C9 C10 65.69(19) . . . . ? C1 C2 C9 C11 74.33(18) . . . . ? C3 C2 C9 C11 -174.19(15) . . . . ? C15 C13 C14 C4 3.2(3) . . . . ? C15 C13 C14 C19 -178.82(16) . . . . ? O2 C4 C14 C13 65.4(2) . . . . ? P1 C4 C14 C13 -107.21(15) . . . . ? O2 C4 C14 C19 -112.70(16) . . . . ? P1 C4 C14 C19 74.67(15) . . . . ? C14 C13 C15 C18 -93.7(2) . . . . ? C14 C13 C15 C16 31.2(3) . . . . ? C14 C13 C15 C17 149.83(19) . . . . ? C13 C14 C19 C21 102.33(19) . . . . ? C4 C14 C19 C21 -79.62(17) . . . . ? C13 C14 C19 C20 -17.9(2) . . . . ? C4 C14 C19 C20 160.11(14) . . . . ? C13 C14 C19 C22 -137.41(16) . . . . ? C4 C14 C19 C22 40.64(18) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.502 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.054 #===END data_06275 _database_code_depnum_ccdc_archive 'CCDC 691156' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H39 O3 P' _chemical_formula_weight 382.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y, z-1/2' _cell_length_a 44.018(15) _cell_length_b 9.170(3) _cell_length_c 23.309(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 9409(5) _cell_formula_units_Z 16 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ireg.plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.580 _exptl_crystal_size_mid 0.240 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.080 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3360 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _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 'Bruker P4' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 61459 _diffrn_reflns_av_R_equivalents 0.2116 _diffrn_reflns_av_sigmaI/netI 0.1254 _diffrn_reflns_limit_h_min -51 _diffrn_reflns_limit_h_max 51 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 24.61 _reflns_number_total 7841 _reflns_number_gt 3881 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0933P)^2^+10.2144P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0033(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 7841 _refine_ls_number_parameters 521 _refine_ls_number_restraints 54 _refine_ls_R_factor_all 0.1738 _refine_ls_R_factor_gt 0.0818 _refine_ls_wR_factor_ref 0.2359 _refine_ls_wR_factor_gt 0.1841 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.004 _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 0.12091(3) 0.22432(17) 0.37075(6) 0.0460(4) Uani 1 1 d . A . O1 O 0.08596(7) 0.4062(4) 0.44745(15) 0.0494(9) Uani 1 1 d . . . H1 H 0.0941 0.3671 0.4751 0.074 Uiso 1 1 calc R . . O2 O 0.13474(8) 0.4487(5) 0.3026(2) 0.0835(15) Uani 1 1 d . A . O3 O 0.13912(7) 0.1086(4) 0.39962(15) 0.0523(10) Uani 1 1 d . . . C1 C 0.09015(10) 0.3237(6) 0.4005(2) 0.0400(12) Uani 1 1 d . . . C4 C 0.14642(11) 0.3670(7) 0.3367(3) 0.0652(18) Uani 1 1 d D . . C3 C 0.09018(10) 0.1977(6) 0.3175(2) 0.0409(13) Uani 1 1 d . . . H3A H 0.0965 0.2321 0.2796 0.049 Uiso 1 1 calc R A . C2 C 0.07412(10) 0.3185(5) 0.3506(2) 0.0377(12) Uani 1 1 d . A . C5 C 0.07661(12) 0.0436(6) 0.3137(2) 0.0475(14) Uani 1 1 d . A . C6 C 0.10158(14) -0.0610(7) 0.2929(3) 0.0708(18) Uani 1 1 d . . . H6A H 0.1098 -0.0261 0.2573 0.106 Uiso 1 1 calc R A . H6B H 0.0931 -0.1564 0.2873 0.106 Uiso 1 1 calc R . . H6C H 0.1174 -0.0658 0.3211 0.106 Uiso 1 1 calc R . . C7 C 0.05070(14) 0.0399(7) 0.2697(2) 0.0682(18) Uani 1 1 d . . . H7A H 0.0583 0.0691 0.2329 0.102 Uiso 1 1 calc R A . H7B H 0.0349 0.1055 0.2815 0.102 Uiso 1 1 calc R . . H7C H 0.0427 -0.0573 0.2673 0.102 Uiso 1 1 calc R . . C8 C 0.06437(11) -0.0078(6) 0.3713(2) 0.0488(14) Uani 1 1 d . . . H8A H 0.0807 -0.0124 0.3986 0.073 Uiso 1 1 calc R A . H8B H 0.0555 -0.1029 0.3670 0.073 Uiso 1 1 calc R . . H8C H 0.0492 0.0593 0.3847 0.073 Uiso 1 1 calc R . . C9 C 0.04867(10) 0.4209(6) 0.3313(2) 0.0450(13) Uani 1 1 d . . . C10 C 0.04751(13) 0.4303(7) 0.2658(2) 0.0611(16) Uani 1 1 d . A . H10A H 0.0669 0.4613 0.2515 0.092 Uiso 1 1 calc R . . H10B H 0.0322 0.4992 0.2546 0.092 Uiso 1 1 calc R . . H10C H 0.0427 0.3361 0.2503 0.092 Uiso 1 1 calc R . . C11 C 0.01768(11) 0.3657(7) 0.3550(3) 0.0624(17) Uani 1 1 d . A . H11A H 0.0185 0.3618 0.3961 0.094 Uiso 1 1 calc R . . H11B H 0.0136 0.2700 0.3401 0.094 Uiso 1 1 calc R . . H11C H 0.0018 0.4312 0.3433 0.094 Uiso 1 1 calc R . . C12 C 0.05422(14) 0.5728(7) 0.3546(3) 0.0693(18) Uani 1 1 d . A . H12A H 0.0540 0.5702 0.3958 0.104 Uiso 1 1 calc R . . H12B H 0.0386 0.6373 0.3412 0.104 Uiso 1 1 calc R . . H12C H 0.0736 0.6073 0.3417 0.104 Uiso 1 1 calc R . . C13 C 0.17908(13) 0.3922(8) 0.3587(3) 0.050(2) Uani 0.730(8) 1 d PD A 1 C14 C 0.20124(15) 0.3108(8) 0.3389(3) 0.054(2) Uani 0.730(8) 1 d PD A 1 H14A H 0.2201 0.3305 0.3551 0.065 Uiso 0.730(8) 1 calc PR A 1 C13' C 0.1805(2) 0.3174(19) 0.3312(8) 0.050(2) Uani 0.270(8) 1 d PD A 2 C14' C 0.1943(4) 0.409(2) 0.3667(8) 0.054(2) Uani 0.270(8) 1 d PD A 2 H14B H 0.2152 0.3966 0.3679 0.065 Uiso 0.270(8) 1 calc PR A 2 C15 C 0.20154(11) 0.1963(7) 0.2966(2) 0.0559(16) Uani 1 1 d D . . C16 C 0.17460(13) 0.1655(9) 0.2582(3) 0.082(2) Uani 1 1 d . A . H16A H 0.1575 0.1372 0.2813 0.124 Uiso 1 1 calc R . . H16B H 0.1796 0.0881 0.2322 0.124 Uiso 1 1 calc R . . H16C H 0.1696 0.2517 0.2368 0.124 Uiso 1 1 calc R . . C17 C 0.20916(19) 0.0566(10) 0.3295(4) 0.120(3) Uani 1 1 d . A . H17A H 0.1926 0.0319 0.3544 0.180 Uiso 1 1 calc R . . H17B H 0.2272 0.0717 0.3520 0.180 Uiso 1 1 calc R . . H17C H 0.2125 -0.0215 0.3028 0.180 Uiso 1 1 calc R . . C18 C 0.22813(16) 0.2395(11) 0.2570(4) 0.121(3) Uani 1 1 d . A . H18A H 0.2235 0.3301 0.2383 0.181 Uiso 1 1 calc R . . H18B H 0.2311 0.1649 0.2287 0.181 Uiso 1 1 calc R . . H18C H 0.2463 0.2504 0.2794 0.181 Uiso 1 1 calc R . . C19 C 0.18365(11) 0.5240(6) 0.4041(2) 0.0571(16) Uani 1 1 d D . . C20 C 0.15885(17) 0.5058(11) 0.4480(3) 0.076(3) Uani 0.723(6) 1 d PD A 1 H20A H 0.1607 0.4120 0.4660 0.114 Uiso 0.723(6) 1 calc PR A 1 H20B H 0.1394 0.5129 0.4295 0.114 Uiso 0.723(6) 1 calc PR A 1 H20C H 0.1606 0.5809 0.4765 0.114 Uiso 0.723(6) 1 calc PR A 1 C21 C 0.1831(2) 0.6640(10) 0.3743(4) 0.091(3) Uani 0.723(6) 1 d PD A 1 H21A H 0.1978 0.6632 0.3439 0.136 Uiso 0.723(6) 1 calc PR A 1 H21B H 0.1879 0.7406 0.4009 0.136 Uiso 0.723(6) 1 calc PR A 1 H21C H 0.1632 0.6802 0.3586 0.136 Uiso 0.723(6) 1 calc PR A 1 C22 C 0.21433(16) 0.5053(12) 0.4372(4) 0.087(3) Uani 0.723(6) 1 d PD A 1 H22A H 0.2157 0.4076 0.4518 0.130 Uiso 0.723(6) 1 calc PR A 1 H22B H 0.2151 0.5732 0.4685 0.130 Uiso 0.723(6) 1 calc PR A 1 H22C H 0.2310 0.5235 0.4116 0.130 Uiso 0.723(6) 1 calc PR A 1 C20' C 0.2073(4) 0.650(2) 0.3962(9) 0.076(3) Uani 0.277(6) 1 d PD A 2 H20D H 0.2274 0.6097 0.3948 0.114 Uiso 0.277(6) 1 calc PR A 2 H20E H 0.2058 0.7165 0.4279 0.114 Uiso 0.277(6) 1 calc PR A 2 H20F H 0.2031 0.7009 0.3611 0.114 Uiso 0.277(6) 1 calc PR A 2 C21' C 0.1817(6) 0.491(3) 0.4673(6) 0.091(3) Uani 0.277(6) 1 d PD A 2 H21D H 0.2015 0.4654 0.4814 0.136 Uiso 0.277(6) 1 calc PR A 2 H21E H 0.1680 0.4116 0.4734 0.136 Uiso 0.277(6) 1 calc PR A 2 H21F H 0.1745 0.5758 0.4873 0.136 Uiso 0.277(6) 1 calc PR A 2 C22' C 0.1527(3) 0.605(3) 0.3891(10) 0.087(3) Uani 0.277(6) 1 d PD A 2 H22D H 0.1521 0.6261 0.3488 0.130 Uiso 0.277(6) 1 calc PR A 2 H22E H 0.1516 0.6949 0.4103 0.130 Uiso 0.277(6) 1 calc PR A 2 H22F H 0.1359 0.5441 0.3993 0.130 Uiso 0.277(6) 1 calc PR A 2 P2 P 0.11201(3) 0.12967(15) 0.55528(6) 0.0433(4) Uani 1 1 d . B . O4 O 0.12098(8) -0.0971(4) 0.47168(16) 0.0557(10) Uani 1 1 d . . . H4 H 0.1270 -0.0359 0.4487 0.084 Uiso 1 1 calc R . . O5 O 0.13744(8) -0.0149(5) 0.64322(19) 0.0754(13) Uani 1 1 d . B . O6 O 0.11612(7) 0.2807(4) 0.53177(14) 0.0488(9) Uani 1 1 d . . . C23 C 0.10620(10) -0.0297(6) 0.5153(2) 0.0424(13) Uani 1 1 d . . . C26 C 0.14314(12) 0.0796(7) 0.6083(3) 0.0648(18) Uani 1 1 d D . . C25 C 0.07777(10) 0.0516(5) 0.5893(2) 0.0376(12) Uani 1 1 d . . . H25A H 0.0813 0.0341 0.6302 0.045 Uiso 1 1 calc R B . C24 C 0.08569(10) -0.0833(5) 0.5543(2) 0.0388(12) Uani 1 1 d . B . C27 C 0.04694(10) 0.1341(6) 0.5796(2) 0.0423(13) Uani 1 1 d . B . C28 C 0.03918(11) 0.1498(7) 0.5171(2) 0.0582(16) Uani 1 1 d . . . H28A H 0.0215 0.2104 0.5131 0.087 Uiso 1 1 calc R B . H28B H 0.0351 0.0553 0.5011 0.087 Uiso 1 1 calc R . . H28C H 0.0560 0.1936 0.4972 0.087 Uiso 1 1 calc R . . C29 C 0.02066(11) 0.0563(7) 0.6105(2) 0.0584(16) Uani 1 1 d . . . H29A H 0.0024 0.1129 0.6066 0.088 Uiso 1 1 calc R B . H29B H 0.0255 0.0456 0.6504 0.088 Uiso 1 1 calc R . . H29C H 0.0176 -0.0382 0.5937 0.088 Uiso 1 1 calc R . . C30 C 0.05030(13) 0.2860(6) 0.6076(3) 0.0651(17) Uani 1 1 d . . . H30A H 0.0312 0.3366 0.6058 0.098 Uiso 1 1 calc R B . H30B H 0.0655 0.3410 0.5875 0.098 Uiso 1 1 calc R . . H30C H 0.0562 0.2747 0.6470 0.098 Uiso 1 1 calc R . . C31 C 0.07668(10) -0.2405(5) 0.5631(2) 0.0409(12) Uani 1 1 d . . . C32 C 0.04994(12) -0.2805(6) 0.5239(2) 0.0570(15) Uani 1 1 d . B . H32A H 0.0551 -0.2581 0.4848 0.086 Uiso 1 1 calc R . . H32B H 0.0323 -0.2256 0.5350 0.086 Uiso 1 1 calc R . . H32C H 0.0457 -0.3828 0.5273 0.086 Uiso 1 1 calc R . . C33 C 0.06788(13) -0.2674(6) 0.6256(2) 0.0548(15) Uani 1 1 d . B . H33A H 0.0848 -0.2454 0.6499 0.082 Uiso 1 1 calc R . . H33B H 0.0622 -0.3677 0.6304 0.082 Uiso 1 1 calc R . . H33C H 0.0510 -0.2059 0.6356 0.082 Uiso 1 1 calc R . . C34 C 0.10370(13) -0.3397(6) 0.5492(3) 0.0607(16) Uani 1 1 d . B . H34A H 0.1084 -0.3327 0.5090 0.091 Uiso 1 1 calc R . . H34B H 0.0987 -0.4387 0.5585 0.091 Uiso 1 1 calc R . . H34C H 0.1210 -0.3097 0.5712 0.091 Uiso 1 1 calc R . . C35 C 0.16766(18) 0.1969(9) 0.6173(5) 0.044(2) Uani 0.50 1 d PD B 1 C36 C 0.1940(2) 0.1593(11) 0.5943(5) 0.055(2) Uani 0.50 1 d PD B 1 H36A H 0.2095 0.2266 0.6001 0.066 Uiso 0.50 1 calc PR B 1 C35' C 0.17704(16) 0.1193(10) 0.5977(5) 0.044(2) Uani 0.50 1 d PD B 2 C36' C 0.1856(2) 0.2432(11) 0.6224(5) 0.055(2) Uani 0.50 1 d PD B 2 H36B H 0.2057 0.2698 0.6166 0.066 Uiso 0.50 1 calc PR B 2 C37 C 0.20310(12) 0.0311(6) 0.5615(3) 0.0599(16) Uani 1 1 d D . . C38 C 0.18888(19) -0.1189(9) 0.5648(4) 0.120(3) Uani 1 1 d . B . H38A H 0.2013 -0.1874 0.5443 0.181 Uiso 1 1 calc R . . H38B H 0.1690 -0.1163 0.5479 0.181 Uiso 1 1 calc R . . H38C H 0.1873 -0.1483 0.6042 0.181 Uiso 1 1 calc R . . C39 C 0.2023(3) 0.0739(12) 0.4992(3) 0.160(5) Uani 1 1 d . B . H39A H 0.2150 0.0089 0.4775 0.239 Uiso 1 1 calc R . . H39B H 0.2097 0.1719 0.4950 0.239 Uiso 1 1 calc R . . H39C H 0.1818 0.0681 0.4852 0.239 Uiso 1 1 calc R . . C40 C 0.23533(17) 0.0189(12) 0.5820(4) 0.138(4) Uani 1 1 d . B . H40A H 0.2455 -0.0571 0.5612 0.207 Uiso 1 1 calc R . . H40B H 0.2355 -0.0040 0.6222 0.207 Uiso 1 1 calc R . . H40C H 0.2456 0.1098 0.5759 0.207 Uiso 1 1 calc R . . C41 C 0.16772(13) 0.3433(6) 0.6574(2) 0.0581(16) Uani 1 1 d D . . C42 C 0.17372(16) 0.4839(8) 0.6261(3) 0.096(2) Uani 1 1 d . B . H42A H 0.1661 0.5641 0.6484 0.143 Uiso 1 1 calc R . . H42B H 0.1637 0.4820 0.5896 0.143 Uiso 1 1 calc R . . H42C H 0.1952 0.4954 0.6204 0.143 Uiso 1 1 calc R . . C43 C 0.18577(17) 0.3379(10) 0.7126(3) 0.114(3) Uani 1 1 d . B . H43A H 0.1789 0.4137 0.7379 0.171 Uiso 1 1 calc R . . H43B H 0.2069 0.3517 0.7043 0.171 Uiso 1 1 calc R . . H43C H 0.1829 0.2448 0.7307 0.171 Uiso 1 1 calc R . . C44 C 0.13372(14) 0.3453(8) 0.6735(3) 0.084(2) Uani 1 1 d . B . H44A H 0.1296 0.4285 0.6972 0.127 Uiso 1 1 calc R . . H44B H 0.1287 0.2578 0.6940 0.127 Uiso 1 1 calc R . . H44C H 0.1217 0.3509 0.6392 0.127 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 0.0245(6) 0.0548(9) 0.0587(9) 0.0142(8) 0.0023(6) -0.0016(7) O1 0.047(2) 0.046(2) 0.054(2) 0.0026(19) -0.0129(18) -0.0039(17) O2 0.037(2) 0.107(4) 0.107(4) 0.061(3) -0.009(2) -0.020(2) O3 0.0295(17) 0.065(3) 0.062(2) 0.024(2) 0.0066(16) 0.0078(18) C1 0.032(2) 0.041(3) 0.048(3) 0.003(3) -0.001(2) -0.005(2) C4 0.031(3) 0.085(5) 0.079(4) 0.037(4) -0.007(3) -0.014(3) C3 0.029(2) 0.051(3) 0.043(3) -0.001(3) 0.003(2) -0.001(2) C2 0.027(2) 0.038(3) 0.048(3) 0.004(2) 0.002(2) -0.006(2) C5 0.050(3) 0.045(4) 0.047(3) -0.001(3) 0.004(3) -0.008(3) C6 0.069(4) 0.055(4) 0.089(5) -0.008(3) 0.030(4) 0.006(3) C7 0.083(4) 0.068(5) 0.053(4) -0.011(3) -0.015(3) -0.027(4) C8 0.044(3) 0.038(3) 0.064(4) -0.003(3) 0.002(3) -0.004(3) C9 0.032(3) 0.046(4) 0.057(4) -0.003(3) -0.005(2) 0.000(2) C10 0.056(3) 0.071(4) 0.056(4) 0.011(3) -0.007(3) 0.011(3) C11 0.033(3) 0.075(4) 0.080(4) 0.009(3) 0.004(3) 0.003(3) C12 0.076(4) 0.053(4) 0.079(5) 0.000(3) -0.024(4) 0.016(3) C13 0.024(3) 0.059(7) 0.066(7) 0.015(4) -0.002(4) -0.012(4) C14 0.030(4) 0.075(6) 0.056(5) 0.000(4) 0.001(3) -0.008(4) C13' 0.024(3) 0.059(7) 0.066(7) 0.015(4) -0.002(4) -0.012(4) C14' 0.030(4) 0.075(6) 0.056(5) 0.000(4) 0.001(3) -0.008(4) C15 0.034(3) 0.068(4) 0.065(4) -0.015(3) -0.001(3) 0.001(3) C16 0.051(3) 0.128(7) 0.069(4) -0.022(4) 0.013(3) -0.020(4) C17 0.099(6) 0.124(8) 0.137(7) 0.014(6) 0.004(5) 0.055(6) C18 0.061(4) 0.171(9) 0.130(7) -0.028(6) 0.025(4) -0.051(5) C19 0.048(3) 0.070(4) 0.053(4) -0.003(3) 0.006(3) -0.015(3) C20 0.053(5) 0.107(8) 0.068(6) -0.022(5) 0.004(4) -0.029(5) C21 0.118(8) 0.071(7) 0.083(7) 0.000(5) -0.010(6) -0.025(6) C22 0.046(4) 0.114(8) 0.101(7) -0.023(6) -0.014(5) -0.010(5) C20' 0.053(5) 0.107(8) 0.068(6) -0.022(5) 0.004(4) -0.029(5) C21' 0.118(8) 0.071(7) 0.083(7) 0.000(5) -0.010(6) -0.025(6) C22' 0.046(4) 0.114(8) 0.101(7) -0.023(6) -0.014(5) -0.010(5) P2 0.0304(6) 0.0449(9) 0.0546(9) 0.0065(7) -0.0060(6) -0.0055(6) O4 0.055(2) 0.055(2) 0.057(2) 0.0106(19) 0.0149(19) 0.0088(19) O5 0.048(2) 0.092(3) 0.086(3) 0.038(3) -0.020(2) -0.013(2) O6 0.0457(19) 0.046(2) 0.055(2) 0.0082(18) -0.0064(16) -0.0115(17) C23 0.033(2) 0.042(3) 0.053(3) 0.003(3) 0.000(2) 0.003(2) C26 0.043(3) 0.077(5) 0.075(4) 0.019(4) -0.014(3) -0.017(3) C25 0.031(2) 0.035(3) 0.046(3) 0.002(2) -0.005(2) -0.006(2) C24 0.026(2) 0.041(3) 0.050(3) 0.006(3) -0.005(2) -0.001(2) C27 0.033(3) 0.036(3) 0.058(3) 0.001(3) 0.004(2) 0.000(2) C28 0.031(3) 0.072(4) 0.071(4) 0.012(3) -0.003(3) 0.009(3) C29 0.030(3) 0.064(4) 0.081(4) 0.008(3) 0.007(3) 0.001(3) C30 0.051(3) 0.050(4) 0.094(5) -0.007(3) 0.011(3) 0.011(3) C31 0.041(3) 0.035(3) 0.047(3) 0.003(2) 0.003(2) -0.002(2) C32 0.057(3) 0.051(4) 0.064(4) -0.005(3) -0.007(3) -0.013(3) C33 0.059(3) 0.045(3) 0.061(4) 0.007(3) 0.004(3) -0.002(3) C34 0.060(4) 0.042(4) 0.080(4) 0.001(3) 0.011(3) 0.008(3) C35 0.019(4) 0.043(7) 0.070(7) 0.008(5) -0.009(4) -0.002(4) C36 0.037(5) 0.051(7) 0.078(7) 0.002(5) 0.003(5) 0.009(5) C35' 0.019(4) 0.043(7) 0.070(7) 0.008(5) -0.009(4) -0.002(4) C36' 0.037(5) 0.051(7) 0.078(7) 0.002(5) 0.003(5) 0.009(5) C37 0.055(3) 0.053(4) 0.072(4) 0.000(3) 0.000(3) 0.010(3) C38 0.096(6) 0.100(7) 0.165(8) -0.029(6) 0.038(6) -0.004(5) C39 0.224(12) 0.172(10) 0.083(6) 0.006(6) 0.015(7) 0.111(9) C40 0.071(5) 0.172(10) 0.172(9) -0.047(8) -0.029(5) -0.005(6) C41 0.060(4) 0.056(4) 0.059(4) 0.001(3) 0.009(3) 0.017(3) C42 0.070(4) 0.092(6) 0.125(6) 0.019(5) 0.013(4) -0.005(4) C43 0.093(5) 0.167(9) 0.082(5) -0.003(5) -0.024(4) 0.067(6) C44 0.070(4) 0.114(6) 0.069(4) -0.018(4) 0.011(3) -0.024(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 O3 1.490(4) . ? P1 C1 1.773(5) . ? P1 C3 1.852(5) . ? P1 C4 1.899(6) . ? P1 C2 2.282(5) . ? O1 C1 1.344(6) . ? O2 C4 1.206(6) . ? C1 C2 1.361(7) . ? C4 C13 1.544(7) . ? C4 C13' 1.573(9) . ? C3 C2 1.524(7) . ? C3 C5 1.536(7) . ? C2 C9 1.529(7) . ? C5 C8 1.523(7) . ? C5 C7 1.533(7) . ? C5 C6 1.537(7) . ? C9 C12 1.515(8) . ? C9 C10 1.529(7) . ? C9 C11 1.556(7) . ? C13 C14 1.312(7) . ? C13 C19 1.618(7) . ? C14 C15 1.441(7) . ? C13' C14' 1.327(10) . ? C13' C15 1.655(8) . ? C14' C19 1.445(9) . ? C15 C16 1.512(7) . ? C15 C17 1.531(10) . ? C15 C18 1.542(8) . ? C19 C21 1.459(9) . ? C19 C20 1.506(8) . ? C19 C21' 1.506(12) . ? C19 C22 1.565(8) . ? C19 C20' 1.564(12) . ? C19 C22' 1.590(13) . ? P2 O6 1.501(4) . ? P2 C23 1.753(5) . ? P2 C25 1.847(5) . ? P2 C26 1.902(6) . ? P2 C24 2.271(5) . ? O4 C23 1.355(6) . ? O5 C26 1.215(6) . ? C23 C24 1.373(6) . ? C26 C35 1.538(8) . ? C26 C35' 1.556(8) . ? C25 C24 1.522(7) . ? C25 C27 1.570(6) . ? C24 C31 1.510(7) . ? C27 C28 1.503(7) . ? C27 C29 1.538(7) . ? C27 C30 1.545(7) . ? C31 C33 1.526(7) . ? C31 C34 1.532(7) . ? C31 C32 1.535(7) . ? C35 C36 1.325(8) . ? C35 C41 1.636(8) . ? C36 C37 1.457(8) . ? C35' C36' 1.329(8) . ? C35' C37 1.637(8) . ? C36' C41 1.458(8) . ? C37 C40 1.501(9) . ? C37 C39 1.505(9) . ? C37 C38 1.514(10) . ? C41 C42 1.504(9) . ? C41 C43 1.514(8) . ? C41 C44 1.543(8) . ? 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 C1 126.9(2) . . ? O3 P1 C3 127.0(2) . . ? C1 P1 C3 76.8(2) . . ? O3 P1 C4 111.2(2) . . ? C1 P1 C4 105.1(3) . . ? C3 P1 C4 104.0(2) . . ? O3 P1 C2 147.96(19) . . ? C1 P1 C2 36.6(2) . . ? C3 P1 C2 41.65(19) . . ? C4 P1 C2 100.8(2) . . ? O1 C1 C2 130.1(5) . . ? O1 C1 P1 135.4(4) . . ? C2 C1 P1 92.5(4) . . ? O2 C4 C13 121.5(6) . . ? O2 C4 C13' 122.2(10) . . ? C13 C4 C13' 35.2(5) . . ? O2 C4 P1 116.8(4) . . ? C13 C4 P1 120.9(5) . . ? C13' C4 P1 113.5(9) . . ? C2 C3 C5 121.2(4) . . ? C2 C3 P1 84.5(3) . . ? C5 C3 P1 116.4(4) . . ? C1 C2 C3 102.5(4) . . ? C1 C2 C9 127.6(5) . . ? C3 C2 C9 129.6(4) . . ? C1 C2 P1 50.9(3) . . ? C3 C2 P1 53.9(2) . . ? C9 C2 P1 162.5(3) . . ? C8 C5 C7 108.6(4) . . ? C8 C5 C3 111.8(4) . . ? C7 C5 C3 110.4(4) . . ? C8 C5 C6 109.7(5) . . ? C7 C5 C6 107.9(5) . . ? C3 C5 C6 108.3(4) . . ? C12 C9 C10 108.2(5) . . ? C12 C9 C2 110.0(4) . . ? C10 C9 C2 110.6(4) . . ? C12 C9 C11 108.3(5) . . ? C10 C9 C11 110.0(4) . . ? C2 C9 C11 109.7(4) . . ? C14 C13 C4 119.3(6) . . ? C14 C13 C19 124.2(5) . . ? C4 C13 C19 116.4(5) . . ? C13 C14 C15 131.5(6) . . ? C14' C13' C4 101.6(10) . . ? C14' C13' C15 118.3(8) . . ? C4 C13' C15 140.1(10) . . ? C13' C14' C19 133.7(13) . . ? C14 C15 C16 122.3(5) . . ? C14 C15 C17 105.6(6) . . ? C16 C15 C17 108.2(6) . . ? C14 C15 C18 103.3(5) . . ? C16 C15 C18 106.8(5) . . ? C17 C15 C18 110.4(6) . . ? C14 C15 C13' 34.2(5) . . ? C16 C15 C13' 88.6(6) . . ? C17 C15 C13' 116.1(9) . . ? C18 C15 C13' 122.9(9) . . ? C14' C19 C21 111.2(11) . . ? C14' C19 C20 124.3(10) . . ? C21 C19 C20 114.1(6) . . ? C14' C19 C21' 117.5(14) . . ? C21 C19 C21' 129.8(11) . . ? C20 C19 C21' 43.3(9) . . ? C14' C19 C22 86.4(9) . . ? C21 C19 C22 110.2(6) . . ? C20 C19 C22 106.1(5) . . ? C21' C19 C22 62.9(10) . . ? C14' C19 C20' 104.6(12) . . ? C21 C19 C20' 46.1(8) . . ? C20 C19 C20' 130.0(10) . . ? C21' C19 C20' 107.4(10) . . ? C22 C19 C20' 64.3(9) . . ? C14' C19 C13 26.1(7) . . ? C21 C19 C13 110.2(6) . . ? C20 C19 C13 105.7(5) . . ? C21' C19 C13 118.8(11) . . ? C22 C19 C13 110.3(5) . . ? C20' C19 C13 123.9(9) . . ? C14' C19 C22' 119.2(12) . . ? C21 C19 C22' 57.9(8) . . ? C20 C19 C22' 65.2(8) . . ? C21' C19 C22' 105.0(10) . . ? C22 C19 C22' 153.9(10) . . ? C20' C19 C22' 101.4(10) . . ? C13 C19 C22' 95.8(10) . . ? O6 P2 C23 126.4(2) . . ? O6 P2 C25 127.8(2) . . ? C23 P2 C25 77.6(2) . . ? O6 P2 C26 111.9(2) . . ? C23 P2 C26 104.5(3) . . ? C25 P2 C26 102.5(2) . . ? O6 P2 C24 148.39(19) . . ? C23 P2 C24 37.2(2) . . ? C25 P2 C24 41.81(19) . . ? C26 P2 C24 99.6(2) . . ? O4 C23 C24 130.5(5) . . ? O4 C23 P2 135.1(4) . . ? C24 C23 P2 92.4(4) . . ? O5 C26 C35 123.6(6) . . ? O5 C26 C35' 118.1(6) . . ? C35 C26 C35' 35.4(4) . . ? O5 C26 P2 117.3(4) . . ? C35 C26 P2 115.2(6) . . ? C35' C26 P2 122.1(6) . . ? C24 C25 C27 120.8(4) . . ? C24 C25 P2 84.2(3) . . ? C27 C25 P2 117.1(3) . . ? C23 C24 C31 127.2(5) . . ? C23 C24 C25 102.4(4) . . ? C31 C24 C25 130.0(4) . . ? C23 C24 P2 50.5(3) . . ? C31 C24 P2 162.6(3) . . ? C25 C24 P2 54.0(2) . . ? C28 C27 C29 109.1(4) . . ? C28 C27 C30 110.2(5) . . ? C29 C27 C30 107.0(4) . . ? C28 C27 C25 112.5(4) . . ? C29 C27 C25 111.0(4) . . ? C30 C27 C25 106.9(4) . . ? C24 C31 C33 110.6(4) . . ? C24 C31 C34 109.5(4) . . ? C33 C31 C34 107.7(4) . . ? C24 C31 C32 110.4(4) . . ? C33 C31 C32 109.6(4) . . ? C34 C31 C32 109.1(4) . . ? C36 C35 C26 112.2(7) . . ? C36 C35 C41 116.3(6) . . ? C26 C35 C41 130.7(6) . . ? C35 C36 C37 131.4(9) . . ? C36' C35' C26 113.7(7) . . ? C36' C35' C37 116.6(6) . . ? C26 C35' C37 129.7(7) . . ? C35' C36' C41 129.0(8) . . ? C36 C37 C40 98.7(7) . . ? C36 C37 C39 106.8(7) . . ? C40 C37 C39 110.4(7) . . ? C36 C37 C38 126.4(7) . . ? C40 C37 C38 107.9(7) . . ? C39 C37 C38 106.0(7) . . ? C36 C37 C35' 30.7(5) . . ? C40 C37 C35' 122.3(6) . . ? C39 C37 C35' 110.6(6) . . ? C38 C37 C35' 97.7(5) . . ? C36' C41 C42 100.0(6) . . ? C36' C41 C43 99.9(6) . . ? C42 C41 C43 110.4(6) . . ? C36' C41 C44 131.8(6) . . ? C42 C41 C44 106.1(5) . . ? C43 C41 C44 107.6(5) . . ? C36' C41 C35 33.4(4) . . ? C42 C41 C35 115.3(6) . . ? C43 C41 C35 117.4(6) . . ? C44 C41 C35 98.4(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 P1 C1 O1 55.1(6) . . . . ? C3 P1 C1 O1 -178.2(6) . . . . ? C4 P1 C1 O1 -77.0(6) . . . . ? C2 P1 C1 O1 -164.7(7) . . . . ? O3 P1 C1 C2 -140.1(3) . . . . ? C3 P1 C1 C2 -13.5(3) . . . . ? C4 P1 C1 C2 87.7(3) . . . . ? O3 P1 C4 O2 165.4(5) . . . . ? C1 P1 C4 O2 -54.1(6) . . . . ? C3 P1 C4 O2 25.8(6) . . . . ? C2 P1 C4 O2 -16.8(6) . . . . ? O3 P1 C4 C13 -24.0(6) . . . . ? C1 P1 C4 C13 116.5(5) . . . . ? C3 P1 C4 C13 -163.6(5) . . . . ? C2 P1 C4 C13 153.8(5) . . . . ? O3 P1 C4 C13' 14.9(8) . . . . ? C1 P1 C4 C13' 155.4(7) . . . . ? C3 P1 C4 C13' -124.8(7) . . . . ? C2 P1 C4 C13' -167.3(7) . . . . ? O3 P1 C3 C2 138.6(3) . . . . ? C1 P1 C3 C2 12.1(3) . . . . ? C4 P1 C3 C2 -90.5(3) . . . . ? O3 P1 C3 C5 16.4(5) . . . . ? C1 P1 C3 C5 -110.1(4) . . . . ? C4 P1 C3 C5 147.3(4) . . . . ? C2 P1 C3 C5 -122.2(5) . . . . ? O1 C1 C2 C3 -177.5(5) . . . . ? P1 C1 C2 C3 16.5(4) . . . . ? O1 C1 C2 C9 8.3(8) . . . . ? P1 C1 C2 C9 -157.7(4) . . . . ? O1 C1 C2 P1 166.0(6) . . . . ? C5 C3 C2 C1 101.8(5) . . . . ? P1 C3 C2 C1 -15.8(3) . . . . ? C5 C3 C2 C9 -84.1(6) . . . . ? P1 C3 C2 C9 158.2(4) . . . . ? C5 C3 C2 P1 117.6(5) . . . . ? O3 P1 C2 C1 75.2(5) . . . . ? C3 P1 C2 C1 160.0(4) . . . . ? C4 P1 C2 C1 -100.9(4) . . . . ? O3 P1 C2 C3 -84.8(5) . . . . ? C1 P1 C2 C3 -160.0(4) . . . . ? C4 P1 C2 C3 99.1(3) . . . . ? O3 P1 C2 C9 167.2(11) . . . . ? C1 P1 C2 C9 92.0(13) . . . . ? C3 P1 C2 C9 -108.0(13) . . . . ? C4 P1 C2 C9 -9.0(13) . . . . ? C2 C3 C5 C8 -43.4(6) . . . . ? P1 C3 C5 C8 56.7(5) . . . . ? C2 C3 C5 C7 77.6(6) . . . . ? P1 C3 C5 C7 177.7(4) . . . . ? C2 C3 C5 C6 -164.4(5) . . . . ? P1 C3 C5 C6 -64.3(5) . . . . ? C1 C2 C9 C12 32.3(7) . . . . ? C3 C2 C9 C12 -140.4(5) . . . . ? P1 C2 C9 C12 -45.8(14) . . . . ? C1 C2 C9 C10 151.7(5) . . . . ? C3 C2 C9 C10 -20.9(7) . . . . ? P1 C2 C9 C10 73.6(13) . . . . ? C1 C2 C9 C11 -86.7(6) . . . . ? C3 C2 C9 C11 100.7(6) . . . . ? P1 C2 C9 C11 -164.8(11) . . . . ? O2 C4 C13 C14 -104.2(9) . . . . ? C13' C4 C13 C14 -1.9(16) . . . . ? P1 C4 C13 C14 85.6(8) . . . . ? O2 C4 C13 C19 73.7(9) . . . . ? C13' C4 C13 C19 176(2) . . . . ? P1 C4 C13 C19 -96.5(7) . . . . ? C4 C13 C14 C15 1.9(13) . . . . ? C19 C13 C14 C15 -175.9(7) . . . . ? O2 C4 C13' C14' 97.3(17) . . . . ? C13 C4 C13' C14' -3.1(13) . . . . ? P1 C4 C13' C14' -114.0(16) . . . . ? O2 C4 C13' C15 -82(3) . . . . ? C13 C4 C13' C15 177(4) . . . . ? P1 C4 C13' C15 67(3) . . . . ? C4 C13' C14' C19 2(3) . . . . ? C15 C13' C14' C19 -178.5(19) . . . . ? C13 C14 C15 C16 10.7(13) . . . . ? C13 C14 C15 C17 -113.3(9) . . . . ? C13 C14 C15 C18 130.8(9) . . . . ? C13 C14 C15 C13' 0.5(17) . . . . ? C14' C13' C15 C14 4.3(14) . . . . ? C4 C13' C15 C14 -176(4) . . . . ? C14' C13' C15 C16 -167(2) . . . . ? C4 C13' C15 C16 12(2) . . . . ? C14' C13' C15 C17 83(2) . . . . ? C4 C13' C15 C17 -97(2) . . . . ? C14' C13' C15 C18 -58(2) . . . . ? C4 C13' C15 C18 122(2) . . . . ? C13' C14' C19 C21 -90(3) . . . . ? C13' C14' C19 C20 52(3) . . . . ? C13' C14' C19 C21' 103(3) . . . . ? C13' C14' C19 C22 159(3) . . . . ? C13' C14' C19 C20' -138(3) . . . . ? C13' C14' C19 C13 2.6(17) . . . . ? C13' C14' C19 C22' -26(3) . . . . ? C14 C13 C19 C14' 4(2) . . . . ? C4 C13 C19 C14' -174(3) . . . . ? C14 C13 C19 C21 101.3(9) . . . . ? C4 C13 C19 C21 -76.5(8) . . . . ? C14 C13 C19 C20 -135.0(8) . . . . ? C4 C13 C19 C20 47.2(8) . . . . ? C14 C13 C19 C21' -90.1(14) . . . . ? C4 C13 C19 C21' 92.1(13) . . . . ? C14 C13 C19 C22 -20.6(10) . . . . ? C4 C13 C19 C22 161.5(6) . . . . ? C14 C13 C19 C20' 51.3(14) . . . . ? C4 C13 C19 C20' -126.5(11) . . . . ? C14 C13 C19 C22' 159.2(11) . . . . ? C4 C13 C19 C22' -18.6(10) . . . . ? O6 P2 C23 O4 54.3(6) . . . . ? C25 P2 C23 O4 -177.5(5) . . . . ? C26 P2 C23 O4 -77.7(6) . . . . ? C24 P2 C23 O4 -164.5(7) . . . . ? O6 P2 C23 C24 -141.2(3) . . . . ? C25 P2 C23 C24 -13.0(3) . . . . ? C26 P2 C23 C24 86.9(3) . . . . ? O6 P2 C26 O5 156.6(5) . . . . ? C23 P2 C26 O5 -63.6(6) . . . . ? C25 P2 C26 O5 16.7(6) . . . . ? C24 P2 C26 O5 -25.9(6) . . . . ? O6 P2 C26 C35 -1.8(6) . . . . ? C23 P2 C26 C35 138.0(5) . . . . ? C25 P2 C26 C35 -141.7(5) . . . . ? C24 P2 C26 C35 175.7(5) . . . . ? O6 P2 C26 C35' -41.6(6) . . . . ? C23 P2 C26 C35' 98.2(6) . . . . ? C25 P2 C26 C35' 178.5(5) . . . . ? C24 P2 C26 C35' 135.9(6) . . . . ? O6 P2 C25 C24 138.5(3) . . . . ? C23 P2 C25 C24 11.8(3) . . . . ? C26 P2 C25 C24 -90.6(3) . . . . ? O6 P2 C25 C27 16.8(5) . . . . ? C23 P2 C25 C27 -110.0(4) . . . . ? C26 P2 C25 C27 147.7(4) . . . . ? C24 P2 C25 C27 -121.8(5) . . . . ? O4 C23 C24 C31 7.8(8) . . . . ? P2 C23 C24 C31 -157.9(4) . . . . ? O4 C23 C24 C25 -178.5(5) . . . . ? P2 C23 C24 C25 15.9(3) . . . . ? O4 C23 C24 P2 165.7(6) . . . . ? C27 C25 C24 C23 103.1(5) . . . . ? P2 C25 C24 C23 -15.1(3) . . . . ? C27 C25 C24 C31 -83.4(6) . . . . ? P2 C25 C24 C31 158.4(5) . . . . ? C27 C25 C24 P2 118.2(5) . . . . ? O6 P2 C24 C23 74.3(5) . . . . ? C25 P2 C24 C23 160.7(4) . . . . ? C26 P2 C24 C23 -101.3(4) . . . . ? O6 P2 C24 C31 163.7(11) . . . . ? C23 P2 C24 C31 89.4(12) . . . . ? C25 P2 C24 C31 -109.8(13) . . . . ? C26 P2 C24 C31 -11.9(12) . . . . ? O6 P2 C24 C25 -86.4(4) . . . . ? C23 P2 C24 C25 -160.7(4) . . . . ? C26 P2 C24 C25 98.0(3) . . . . ? C24 C25 C27 C28 -42.4(6) . . . . ? P2 C25 C27 C28 57.5(5) . . . . ? C24 C25 C27 C29 80.1(6) . . . . ? P2 C25 C27 C29 -180.0(4) . . . . ? C24 C25 C27 C30 -163.5(4) . . . . ? P2 C25 C27 C30 -63.6(5) . . . . ? C23 C24 C31 C33 149.8(5) . . . . ? C25 C24 C31 C33 -22.2(7) . . . . ? P2 C24 C31 C33 74.2(13) . . . . ? C23 C24 C31 C34 31.3(7) . . . . ? C25 C24 C31 C34 -140.8(5) . . . . ? P2 C24 C31 C34 -44.3(14) . . . . ? C23 C24 C31 C32 -88.8(6) . . . . ? C25 C24 C31 C32 99.2(6) . . . . ? P2 C24 C31 C32 -164.4(11) . . . . ? O5 C26 C35 C36 94.3(11) . . . . ? C35' C26 C35 C36 1.7(10) . . . . ? P2 C26 C35 C36 -108.9(9) . . . . ? O5 C26 C35 C41 -75.6(12) . . . . ? C35' C26 C35 C41 -168.1(18) . . . . ? P2 C26 C35 C41 81.3(11) . . . . ? C26 C35 C36 C37 2.0(18) . . . . ? C41 C35 C36 C37 173.4(9) . . . . ? O5 C26 C35' C36' -103.5(11) . . . . ? C35 C26 C35' C36' 5.8(10) . . . . ? P2 C26 C35' C36' 94.9(10) . . . . ? O5 C26 C35' C37 76.0(12) . . . . ? C35 C26 C35' C37 -174.8(18) . . . . ? P2 C26 C35' C37 -85.7(11) . . . . ? C26 C35' C36' C41 0.2(17) . . . . ? C37 C35' C36' C41 -179.3(9) . . . . ? C35 C36 C37 C40 -146.6(13) . . . . ? C35 C36 C37 C39 98.9(15) . . . . ? C35 C36 C37 C38 -26.6(18) . . . . ? C35 C36 C37 C35' -3.3(12) . . . . ? C36' C35' C37 C36 -4.7(11) . . . . ? C26 C35' C37 C36 176(2) . . . . ? C36' C35' C37 C40 39.7(14) . . . . ? C26 C35' C37 C40 -139.8(10) . . . . ? C36' C35' C37 C39 -93.1(11) . . . . ? C26 C35' C37 C39 87.5(12) . . . . ? C36' C35' C37 C38 156.5(10) . . . . ? C26 C35' C37 C38 -22.9(12) . . . . ? C35' C36' C41 C42 -127.2(13) . . . . ? C35' C36' C41 C43 119.9(13) . . . . ? C35' C36' C41 C44 -4.7(18) . . . . ? C35' C36' C41 C35 -5.8(11) . . . . ? C36 C35 C41 C36' -1.4(11) . . . . ? C26 C35 C41 C36' 168.1(19) . . . . ? C36 C35 C41 C42 67.1(11) . . . . ? C26 C35 C41 C42 -123.5(10) . . . . ? C36 C35 C41 C43 -65.7(12) . . . . ? C26 C35 C41 C43 103.8(10) . . . . ? C36 C35 C41 C44 179.4(10) . . . . ? C26 C35 C41 C44 -11.1(11) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.61 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.519 _refine_diff_density_min -0.361 _refine_diff_density_rms 0.072