Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Eric James Thomas' _publ_contact_author_address ; School of Chemistry University of Manchester MANCHESTER M13 9PL UNITED KINGDOM ; _publ_contact_author_email E.J.THOMAS@MAN.AC.UK _publ_section_title ; A total synthesis of milbemycin G: approaches to the C(1)-C(10)-fragment and completion of the synthesis ; loop_ _publ_author_name 'E. Thomas' 'Simon Bailey' 'Madeleine Helliwell' 'Aphiwat Teerawutgulrag' data_S400-4 _database_code_depnum_ccdc_archive 'CCDC 275135' #------------------------------------------------------------------------------ _audit_creation_date 19105-06-15 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1993). J. Appl. Cryst., 26, 343. ; #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ; SIR92 (Altomare, et. al. 1993) ; _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 14.153(1) _cell_length_b 14.153 _cell_length_c 25.881(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_volume 4489.3(7) _cell_formula_units_Z 6 _cell_measurement_temperature 296.2 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 14.8 _cell_measurement_theta_max 22.8 #------------------------------------------------------------------------------ _symmetry_cell_setting hexgonal _symmetry_space_group_name_H-M 'P 61 ' _symmetry_Int_Tables_number 169 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -y, +x-y,1/3+z' ' -x+y, -x,2/3+z' ' -x, -y,1/2+z' ' +y, -x+y,5/6+z' ' +x-y, +x,1/6+z' #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.254 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 565.09 _chemical_formula_analytical ? _chemical_formula_sum 'C27 H33 Cl O9 Si ' _chemical_formula_moiety 'C27 H33 Cl O9 Si ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1788.00 _exptl_absorpt_coefficient_mu 1.925 _exptl_absorpt_correction_type ; \y scans (North,Phillips & Matthews, 1968) ; _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.963 _exptl_special_details ; The scan width was (1.05+0.30tan\q)\% with an \w scan speed of 8\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 296.2 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 5.41 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 2592 _reflns_number_total 2292 _reflns_number_observed 1156 _reflns_observed_criterion >3.00\s(I) _diffrn_reflns_av_R_equivalents 0.08139 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 60.08 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 -0.01566 _diffrn_orient_matrix_UB_12 -0.07615 _diffrn_orient_matrix_UB_13 0.00649 _diffrn_orient_matrix_UB_21 -0.08002 _diffrn_orient_matrix_UB_22 -0.02620 _diffrn_orient_matrix_UB_23 0.00015 _diffrn_orient_matrix_UB_31 -0.00299 _diffrn_orient_matrix_UB_32 -0.01308 _diffrn_orient_matrix_UB_33 -0.03809 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 162 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 198 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 54 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Cl 0 6 0.364 0.702 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Si 0 6 0.254 0.330 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Cl1 -0.211(1) 0.889(3) 0.9088 0.26(1) 0.500 . Uani d ? Cl2 -0.228(1) 0.745(2) 0.921(1) 0.30(1) 0.500 . Uani d ? Si1 0.5259(5) 1.0006(5) 0.8571(7) 0.104(2) 1.000 . Uani d ? O1 0.4146(9) 0.8246(9) 0.7911(8) 0.085(5) 1.000 . Uani d ? O2 0.4430(8) 1.1362(7) 0.7932(8) 0.065(3) 1.000 . Uani d ? O3 0.5061(10) 1.094(1) 0.6391(9) 0.106(5) 1.000 . Uani d ? O4 0.582(1) 1.171(1) 0.7132(8) 0.124(6) 1.000 . Uani d ? O5 0.2198(10) 1.1704(9) 0.8024(8) 0.091(5) 1.000 . Uani d ? O6 0.2334(8) 0.9940(8) 0.8249(8) 0.053(3) 1.000 . Uani d ? O7 0.062(1) 0.865(1) 0.8074(8) 0.155(6) 1.000 . Uani d ? O8 0.0184(10) 0.8491(10) 0.9124(8) 0.088(5) 1.000 . Uani d ? O9 0.026(1) 1.004(1) 0.8872(9) 0.145(7) 1.000 . Uani d ? C1 0.452(2) 1.029(2) 0.907(1) 0.121(8) 1.000 . Uiso d ? C2 0.562(2) 0.902(2) 0.884(1) 0.16(1) 1.000 . Uiso d ? C3 0.653(2) 1.125(2) 0.839(1) 0.141(9) 1.000 . Uiso d ? C4 0.435(1) 0.933(1) 0.8002(10) 0.073(5) 1.000 . Uiso d ? C5 0.378(1) 0.952(1) 0.7639(8) 0.047(4) 1.000 . Uiso d ? C6 0.318(1) 0.858(1) 0.7341(9) 0.064(5) 1.000 . Uiso d ? C7 0.343(1) 0.786(1) 0.7514(10) 0.069(5) 1.000 . Uiso d ? C8 0.369(1) 1.056(1) 0.7585(9) 0.054(4) 1.000 . Uiso d ? C9 0.389(1) 1.096(1) 0.7020(9) 0.057(4) 1.000 . Uiso d ? C10 0.503(2) 1.126(2) 0.686(1) 0.080(6) 1.000 . Uiso d ? C11 0.618(2) 1.119(2) 0.622(1) 0.132(8) 1.000 . Uiso d ? C12 0.606(3) 1.101(3) 0.566(2) 0.19(1) 1.000 . Uiso d ? C13 0.375(1) 1.197(1) 0.6957(9) 0.075(5) 1.000 . Uiso d ? C14 0.265(1) 1.175(1) 0.7128(9) 0.077(5) 1.000 . Uiso d ? C15 0.255(2) 1.276(2) 0.709(1) 0.118(7) 1.000 . Uiso d ? C16 0.244(1) 1.133(1) 0.7665(10) 0.066(5) 1.000 . Uiso d ? C17 0.251(1) 1.028(1) 0.7731(9) 0.050(4) 1.000 . Uiso d ? C18 0.134(2) 0.914(2) 0.837(1) 0.079(6) 1.000 . Uiso d ? C19 0.127(1) 0.889(1) 0.8943(9) 0.066(5) 1.000 . Uiso d ? C20 0.158(1) 0.810(1) 0.910(1) 0.082(6) 1.000 . Uiso d ? C21 0.189(2) 0.755(2) 0.875(1) 0.113(7) 1.000 . Uiso d ? C22 0.225(2) 0.684(2) 0.893(1) 0.117(7) 1.000 . Uiso d ? C23 0.215(2) 0.658(2) 0.941(1) 0.143(9) 1.000 . Uiso d ? C24 0.177(2) 0.697(2) 0.977(1) 0.134(9) 1.000 . Uiso d ? C25 0.149(2) 0.778(2) 0.961(1) 0.096(6) 1.000 . Uiso d ? C26 -0.018(2) 0.919(2) 0.906(1) 0.104(7) 1.000 . Uiso d ? C27 -0.121(2) 0.878(2) 0.934(1) 0.156(10) 1.000 . Uiso d ? H1A 0.4322 1.0797 0.8941 0.148 1.000 . Uiso c ? H1B 0.4955 1.0565 0.9365 0.148 1.000 . Uiso c ? H1C 0.3863 0.9622 0.9153 0.148 1.000 . Uiso c ? H2A 0.4980 0.8361 0.8915 0.200 1.000 . Uiso c ? H2B 0.6056 0.9318 0.9132 0.200 1.000 . Uiso c ? H2C 0.6030 0.8879 0.8580 0.200 1.000 . Uiso c ? H3A 0.6909 1.1089 0.8124 0.171 1.000 . Uiso c ? H3B 0.6989 1.1556 0.8675 0.171 1.000 . Uiso c ? H3C 0.6365 1.1782 0.8245 0.171 1.000 . Uiso c ? H6 0.2684 0.8475 0.7064 0.077 1.000 . Uiso c ? H7 0.3140 0.7150 0.7367 0.081 1.000 . Uiso c ? H9 0.3381 1.0389 0.6796 0.069 1.000 . Uiso c ? H11A 0.6375 1.0707 0.6376 0.158 1.000 . Uiso c ? H11B 0.6709 1.1920 0.6292 0.158 1.000 . Uiso c ? H12A 0.5827 1.1456 0.5507 0.219 1.000 . Uiso c ? H12B 0.5572 1.0265 0.5589 0.219 1.000 . Uiso c ? H12C 0.6769 1.1196 0.5518 0.219 1.000 . Uiso c ? H13A 0.3844 1.2174 0.6596 0.091 1.000 . Uiso c ? H13B 0.4296 1.2551 0.7150 0.091 1.000 . Uiso c ? H14 0.2113 1.1211 0.6907 0.092 1.000 . Uiso c ? H15A 0.2658 1.3015 0.6738 0.142 1.000 . Uiso c ? H15B 0.3061 1.3319 0.7303 0.142 1.000 . Uiso c ? H15C 0.1825 1.2591 0.7189 0.142 1.000 . Uiso c ? H17 0.1999 0.9715 0.7507 0.061 1.000 . Uiso c ? H19 0.1730 0.9557 0.9111 0.079 1.000 . Uiso c ? H21 0.1886 0.7668 0.8380 0.130 1.000 . Uiso c ? H22 0.2586 0.6560 0.8694 0.136 1.000 . Uiso c ? H23 0.2334 0.6045 0.9510 0.170 1.000 . Uiso c ? H24 0.1697 0.6737 1.0113 0.157 1.000 . Uiso c ? H25 0.1227 0.8077 0.9855 0.112 1.000 . Uiso c ? H27A -0.1017 0.9209 0.9679 0.174 0.500 . Uiso d ? H27B -0.1483 0.8053 0.9443 0.174 0.500 . Uiso d ? H27C -0.1449 0.9309 0.9324 0.174 0.500 . Uiso d ? H27D -0.1026 0.8782 0.9719 0.174 0.500 . Uiso 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.13(1) 0.56(4) 0.17(2) 0.22(2) 0.03(1) 0.11(3) Cl2 0.11(1) 0.41(4) 0.31(3) 0.08(2) 0.05(2) -0.13(3) Si1 0.100(5) 0.095(4) 0.131(5) 0.059(4) -0.045(4) -0.023(4) O1 0.082(9) 0.073(8) 0.11(1) 0.050(7) -0.014(8) -0.013(8) O2 0.063(7) 0.033(6) 0.082(8) 0.011(5) -0.029(6) -0.031(5) O3 0.083(9) 0.11(1) 0.11(1) 0.036(8) 0.033(9) -0.007(9) O4 0.062(9) 0.16(1) 0.10(1) 0.019(9) 0.005(8) 0.01(1) O5 0.14(1) 0.092(9) 0.064(8) 0.079(9) 0.015(8) -0.014(7) O6 0.062(7) 0.069(7) 0.034(6) 0.037(6) -0.006(5) -0.007(5) O7 0.11(1) 0.16(1) 0.072(10) -0.02(1) -0.030(9) -0.001(10) O8 0.095(9) 0.081(9) 0.10(1) 0.055(8) 0.030(8) 0.023(8) O9 0.12(1) 0.13(1) 0.20(2) 0.07(1) 0.00(1) 0.06(1) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 1156 _refine_ls_number_parameters 0 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0907 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0954 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 2.499 _refine_ls_shift/esd_max 0.0000 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.28 _refine_diff_density_max 0.26 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag CL1 CL2 1.96(5) . . yes CL1 C27 1.52(5) . . yes CL1 H27C 1.03 . . no CL2 C27 1.76(3) . . yes CL2 H27B 1.18 . . no SI1 C1 1.83(3) . . yes SI1 C2 1.85(4) . . yes SI1 C3 1.85(2) . . yes SI1 C4 1.87(3) . . yes O1 C4 1.44(2) . . yes O1 C7 1.35(3) . . yes O2 C8 1.41(2) . . yes O3 C10 1.31(4) . . yes O3 C11 1.51(3) . . yes O4 C10 1.20(3) . . yes O5 C16 1.20(3) . . yes O6 C17 1.40(3) . . yes O6 C18 1.32(2) . . yes O7 C18 1.18(3) . . yes O8 C19 1.43(2) . . yes O8 C26 1.32(4) . . yes O9 C26 1.16(3) . . yes C1 H1A 0.95 . . no C1 H1B 0.93 . . no C1 H1C 0.96 . . no C2 H2A 0.94 . . no C2 H2B 0.94 . . no C2 H2C 0.96 . . no C3 H3A 0.96 . . no C3 H3B 0.94 . . no C3 H3C 0.96 . . no C4 C5 1.34(3) . . yes C5 C6 1.40(2) . . yes C5 C8 1.55(3) . . yes C6 C7 1.31(3) . . yes C6 H6 0.96 . . no C7 H7 0.96 . . no C8 C9 1.54(3) . . yes C8 C17 1.56(2) . . yes C9 C10 1.50(3) . . yes C9 C13 1.54(3) . . yes C9 H9 0.96 . . no C11 C12 1.47(5) . . yes C11 H11A 0.94 . . no C11 H11B 0.94 . . no C12 H12A 0.94 . . no C12 H12B 0.94 . . no C12 H12C 0.97 . . no C13 C14 1.50(3) . . yes C13 H13A 0.97 . . no C13 H13B 0.94 . . no C14 C15 1.51(4) . . yes C14 C16 1.48(3) . . yes C14 H14 0.96 . . no C15 H15A 0.97 . . no C15 H15B 0.93 . . no C15 H15C 0.96 . . no C16 C17 1.56(3) . . yes C17 H17 0.96 . . no C18 C19 1.52(4) . . yes C19 C20 1.45(3) . . yes C19 H19 0.94 . . no C20 C21 1.41(4) . . yes C20 C25 1.38(4) . . yes C21 C22 1.42(4) . . yes C21 H21 0.96 . . no C22 C23 1.28(5) . . yes C22 H22 0.96 . . no C23 C24 1.33(5) . . yes C23 H23 0.95 . . no C24 C25 1.44(4) . . yes C24 H24 0.93 . . no C25 H25 0.93 . . no C26 C27 1.47(4) . . yes C27 H27A 1.01 . . no C27 H27B 0.94 . . no C27 H27C 0.96 . . no C27 H27D 1.00 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag CL2 CL1 C27 59(1) . . . yes CL2 CL1 H27C 95.7 . . . no C27 CL1 H27C 38.7 . . . no CL1 CL2 C27 47(1) . . . yes CL1 CL2 H27B 75.8 . . . no C27 CL2 H27B 29.5 . . . no C1 SI1 C2 108(1) . . . yes C1 SI1 C3 111(1) . . . yes C1 SI1 C4 109(1) . . . yes C2 SI1 C3 108(1) . . . yes C2 SI1 C4 106(1) . . . yes C3 SI1 C4 112(1) . . . yes C4 O1 C7 105(1) . . . yes C10 O3 C11 113(1) . . . yes C17 O6 C18 116(1) . . . yes C19 O8 C26 113(1) . . . yes SI1 C1 H1A 109.5 . . . no SI1 C1 H1B 109.9 . . . no SI1 C1 H1C 108.8 . . . no H1A C1 H1B 110.5 . . . no H1A C1 H1C 108.2 . . . no H1B C1 H1C 110.0 . . . no SI1 C2 H2A 109.4 . . . no SI1 C2 H2B 109.0 . . . no SI1 C2 H2C 108.9 . . . no H2A C2 H2B 110.9 . . . no H2A C2 H2C 109.3 . . . no H2B C2 H2C 109.4 . . . no SI1 C3 H3A 110.1 . . . no SI1 C3 H3B 110.6 . . . no SI1 C3 H3C 110.1 . . . no H3A C3 H3B 109.2 . . . no H3A C3 H3C 107.4 . . . no H3B C3 H3C 109.4 . . . no SI1 C4 O1 112(1) . . . yes SI1 C4 C5 141(1) . . . yes O1 C4 C5 105(1) . . . yes C4 C5 C6 109(1) . . . yes C4 C5 C8 126(1) . . . yes C6 C5 C8 123(1) . . . yes C5 C6 C7 105(1) . . . yes C5 C6 H6 127.2 . . . no C7 C6 H6 127.1 . . . no O1 C7 C6 113(1) . . . yes O1 C7 H7 124.4 . . . no C6 C7 H7 122.4 . . . no O2 C8 C5 109(1) . . . yes O2 C8 C9 112(1) . . . yes O2 C8 C17 108(1) . . . yes C5 C8 C9 110(1) . . . yes C5 C8 C17 108(1) . . . yes C9 C8 C17 107(1) . . . yes C8 C9 C10 109(1) . . . yes C8 C9 C13 110(1) . . . yes C8 C9 H9 109.9 . . . no C10 C9 C13 108(1) . . . yes C10 C9 H9 108.9 . . . no C13 C9 H9 109.0 . . . no O3 C10 O4 122(2) . . . yes O3 C10 C9 111(1) . . . yes O4 C10 C9 125(2) . . . yes O3 C11 C12 103(2) . . . yes O3 C11 H11A 111.2 . . . no O3 C11 H11B 110.9 . . . no C12 C11 H11A 110.2 . . . no C12 C11 H11B 109.8 . . . no H11A C11 H11B 111.1 . . . no C11 C12 H12A 110.0 . . . no C11 C12 H12B 109.8 . . . no C11 C12 H12C 108.2 . . . no H12A C12 H12B 111.0 . . . no H12A C12 H12C 108.8 . . . no H12B C12 H12C 109.0 . . . no C9 C13 C14 112(1) . . . yes C9 C13 H13A 108.6 . . . no C9 C13 H13B 109.1 . . . no C14 C13 H13A 108.5 . . . no C14 C13 H13B 109.5 . . . no H13A C13 H13B 108.5 . . . no C13 C14 C15 111(1) . . . yes C13 C14 C16 109(1) . . . yes C13 C14 H14 108.2 . . . no C15 C14 C16 110(2) . . . yes C15 C14 H14 108.2 . . . no C16 C14 H14 108.6 . . . no C14 C15 H15A 109.5 . . . no C14 C15 H15B 111.1 . . . no C14 C15 H15C 109.6 . . . no H15A C15 H15B 109.4 . . . no H15A C15 H15C 107.2 . . . no H15B C15 H15C 110.0 . . . no O5 C16 C14 126(2) . . . yes O5 C16 C17 120(2) . . . yes C14 C16 C17 112(1) . . . yes O6 C17 C8 107(1) . . . yes O6 C17 C16 110(1) . . . yes O6 C17 H17 111.5 . . . no C8 C17 C16 107(1) . . . yes C8 C17 H17 109.7 . . . no C16 C17 H17 110.1 . . . no O6 C18 O7 125(2) . . . yes O6 C18 C19 110(1) . . . yes O7 C18 C19 124(1) . . . yes O8 C19 C18 110(1) . . . yes O8 C19 C20 106(1) . . . yes O8 C19 H19 108.1 . . . no C18 C19 C20 116(2) . . . yes C18 C19 H19 106.5 . . . no C20 C19 H19 108.6 . . . no C19 C20 C21 122(2) . . . yes C19 C20 C25 120(2) . . . yes C21 C20 C25 116(2) . . . yes C20 C21 C22 119(2) . . . yes C20 C21 H21 121.4 . . . no C22 C21 H21 119.0 . . . no C21 C22 C23 119(3) . . . yes C21 C22 H22 120.0 . . . no C23 C22 H22 120.7 . . . no C22 C23 C24 125(3) . . . yes C22 C23 H23 116.6 . . . no C24 C23 H23 118.0 . . . no C23 C24 C25 117(2) . . . yes C23 C24 H24 121.0 . . . no C25 C24 H24 121.6 . . . no C20 C25 C24 120(2) . . . yes C20 C25 H25 119.4 . . . no C24 C25 H25 119.8 . . . no O8 C26 O9 128(2) . . . yes O8 C26 C27 109(2) . . . yes O9 C26 C27 121(3) . . . yes CL1 C27 CL2 73(2) . . . yes CL1 C27 C26 117(2) . . . yes CL1 C27 H27A 107.6 . . . no CL1 C27 H27B 109.2 . . . no CL1 C27 H27C 41.8 . . . no CL1 C27 H27D 131.0 . . . no CL2 C27 C26 117(2) . . . yes CL2 C27 H27A 130.0 . . . no CL2 C27 H27B 38.5 . . . no CL2 C27 H27C 112.0 . . . no CL2 C27 H27D 106.1 . . . no C26 C27 H27A 105.8 . . . no C26 C27 H27B 110.1 . . . no C26 C27 H27C 109.8 . . . no C26 C27 H27D 105.6 . . . no H27A C27 H27B 105.4 . . . no H27A C27 H27C 71.2 . . . no H27A C27 H27D 35.2 . . . no H27B C27 H27C 139.2 . . . no H27B C27 H27D 72.7 . . . no H27C C27 H27D 104.2 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag CL1 C2 3.36(5) . 1_455 no O4 C22 3.58(4) . 5_564 no O5 C9 3.22(2) . 6_665 no O5 C14 3.41(3) . 6_665 no O5 C13 3.58(2) . 6_665 no O5 O9 3.59(3) . 5_454 no O7 C19 2.97(3) . 5_454 no O7 O9 3.10(3) . 5_454 no O7 C26 3.20(3) . 5_454 no O7 O8 3.23(2) . 5_454 no O9 C16 3.21(3) . 6_665 no O9 C14 3.34(3) . 6_665 no O9 C17 3.48(2) . 6_665 no #------------------------------------------------------------------------------ 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 CL1 CL2 C27 C26 . . . . -113(3) no CL1 C27 C26 O8 . . . . -139(2) no CL1 C27 C26 O9 . . . . 47(4) no CL2 CL1 C27 C26 . . . . 113(3) no CL2 C27 C26 O8 . . . . -54(3) no CL2 C27 C26 O9 . . . . 132(3) no SI1 C4 O1 C7 . . . . 176(1) no SI1 C4 C5 C6 . . . . -175(1) no SI1 C4 C5 C8 . . . . -1(3) no O1 C4 SI1 C1 . . . . -116(1) no O1 C4 SI1 C2 . . . . 0(1) no O1 C4 SI1 C3 . . . . 118(1) no O1 C4 C5 C6 . . . . 3(2) no O1 C4 C5 C8 . . . . 177(1) no O1 C7 C6 C5 . . . . 1(2) no O2 C8 C5 C4 . . . . 8(2) no O2 C8 C5 C6 . . . . -178(1) no O2 C8 C9 C10 . . . . 59(2) no O2 C8 C9 C13 . . . . -60(1) no O2 C8 C17 O6 . . . . -56(1) no O2 C8 C17 C16 . . . . 62(2) no O3 C10 C9 C8 . . . . 139(1) no O3 C10 C9 C13 . . . . -99(2) no O4 C10 O3 C11 . . . . 0(3) no O4 C10 C9 C8 . . . . -38(2) no O4 C10 C9 C13 . . . . 82(2) no O5 C16 C14 C13 . . . . 124(1) no O5 C16 C14 C15 . . . . 1(2) no O5 C16 C17 O6 . . . . -3(1) no O5 C16 C17 C8 . . . . -120(1) no O6 C17 C8 C5 . . . . 62(1) no O6 C17 C8 C9 . . . . -178(1) no O6 C17 C16 C14 . . . . 178(1) no O6 C18 C19 O8 . . . . 150(1) no O6 C18 C19 C20 . . . . -88(2) no O7 C18 O6 C17 . . . . 4(3) no O7 C18 C19 O8 . . . . -32(3) no O7 C18 C19 C20 . . . . 89(3) no O8 C19 C20 C21 . . . . 120(1) no O8 C19 C20 C25 . . . . -53(2) no O9 C26 O8 C19 . . . . 2(4) no C1 SI1 C4 C5 . . . . 62(2) no C2 SI1 C4 C5 . . . . 179(2) no C3 SI1 C4 C5 . . . . -62(2) no C4 O1 C7 C6 . . . . 1(2) no C4 C5 C6 C7 . . . . -3(2) no C4 C5 C8 C9 . . . . 132(1) no C4 C5 C8 C17 . . . . -109(2) no C5 C4 O1 C7 . . . . -2(2) no C5 C8 C9 C10 . . . . -62(1) no C5 C8 C9 C13 . . . . 177(1) no C5 C8 C17 C16 . . . . -179(1) no C6 C5 C8 C9 . . . . -54(2) no C6 C5 C8 C17 . . . . 63(2) no C7 C6 C5 C8 . . . . -176(1) no C8 C9 C13 C14 . . . . -56(1) no C8 C17 O6 C18 . . . . -143(1) no C8 C17 C16 C14 . . . . 61(1) no C9 C8 C17 C16 . . . . -59(1) no C9 C10 O3 C11 . . . . -177(1) no C9 C13 C14 C15 . . . . 176(1) no C9 C13 C14 C16 . . . . 54(2) no C10 O3 C11 C12 . . . . -166(2) no C10 C9 C8 C17 . . . . 179(1) no C10 C9 C13 C14 . . . . -177(1) no C13 C9 C8 C17 . . . . 59(1) no C13 C14 C16 C17 . . . . -57(1) no C15 C14 C16 C17 . . . . 179(1) no C16 C17 O6 C18 . . . . 99(1) no C17 O6 C18 C19 . . . . -178(1) no C18 C19 O8 C26 . . . . -60(2) no C18 C19 C20 C21 . . . . -2(2) no C18 C19 C20 C25 . . . . -176(1) no C19 O8 C26 C27 . . . . -169(2) no C19 C20 C21 C22 . . . . 175(1) no C19 C20 C25 C24 . . . . 178(1) no C20 C19 O8 C26 . . . . 172(2) no C20 C21 C22 C23 . . . . 9(2) no C20 C25 C24 C23 . . . . 2(2) no C21 C20 C25 C24 . . . . 4(2) no C21 C22 C23 C24 . . . . -3(3) no C22 C21 C20 C25 . . . . -9(2) no C22 C23 C24 C25 . . . . -2(3) no #------------------------------------------------------------------------------ data_S171/2 _database_code_depnum_ccdc_archive 'CCDC 275136' #------------------------------------------------------------------------------ _audit_creation_date 19105-06-15 _audit_creation_method 'by teXsan v1.7' _audit_update_record ; ? ; _publ_section_references ; ENTER OTHER REFERENCES Molecular Structure Corporation. (1995). teXsan. Single Crystal Structure Analysis Software. Version 1.7. MSC, 3200 Research Forest Drive, The Woodlands, TX 77381, USA. Walker, N. & Stuart. D. (1983). Acta Cryst. A39, 158-166. ; loop_ _publ_manuscript_incl_extra_item '_geom_extra_table_head_3' '_geom_bond_atom_site_label_D' '_geom_bond_atom_site_label_H' '_geom_contact_atom_site_label_A' '_geom_bond_distance_DH' '_geom_contact_distance_HA' '_geom_contact_distance_DA' '_geom_angle_DHA' '_geom_contact_site_symmetry_A' # # #------------------------------------------------------------------------------ _computing_data_collection 'MSC/AFC Diffractometer Control' _computing_cell_refinement 'MSC/AFC Diffractometer Control' _computing_data_reduction 'teXsan (MSC, 1995)' _computing_structure_solution ? _computing_structure_refinement 'teXsan (MSC, 1995)' _computing_publication_material 'teXsan (MSC, 1995)' #------------------------------------------------------------------------------ _cell_length_a 14.792(2) _cell_length_b 28.300(4) _cell_length_c 8.5666(9) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 3586.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 23 _cell_measurement_theta_min 19.1 _cell_measurement_theta_max 19.9 #------------------------------------------------------------------------------ _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x, -y,1/2+z' '1/2+x,1/2-y, -z' ' -x,1/2+y,1/2-z' #------------------------------------------------------------------------------ _exptl_crystal_description tabular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.15 _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 652.81 _chemical_formula_analytical ? _chemical_formula_sum 'C35 H44 O10 Si ' _chemical_formula_moiety 'C35 H44 O10 Si ' _chemical_formula_structural ? _chemical_compound_source ? _exptl_crystal_F_000 1392.00 _exptl_absorpt_coefficient_mu 1.027 _exptl_absorpt_correction_type ; \DF (DIFABS; Walker & Stuart, 1983) ; _exptl_absorpt_correction_T_max 1.123 _exptl_absorpt_correction_T_min 0.773 _exptl_special_details ; The scan width was (1.10+0.30tan\q)\% with an \w scan speed of 16\% per minute (up to 4 scans to achieve I/\s(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1. ; #------------------------------------------------------------------------------ _diffrn_special_details ; ? ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Rigaku rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'Rigaku Rigaku_AFC5R' _diffrn_measurement_method \w-2\q _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_decay_% -4.90 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l ? ? ? ? ? ? ? ? ? _diffrn_reflns_number 3060 _reflns_number_total 3060 _reflns_number_observed 2565 _reflns_observed_criterion >3.00\s(I) _diffrn_reflns_av_R_equivalents 0.00000 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 0.00 _diffrn_reflns_theta_max 59.90 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.05892 _diffrn_orient_matrix_UB_12 0.00426 _diffrn_orient_matrix_UB_13 0.05550 _diffrn_orient_matrix_UB_21 -0.00049 _diffrn_orient_matrix_UB_22 -0.03413 _diffrn_orient_matrix_UB_23 0.03016 _diffrn_orient_matrix_UB_31 0.03315 _diffrn_orient_matrix_UB_32 -0.00808 _diffrn_orient_matrix_UB_33 -0.09817 #------------------------------------------------------------------------------ loop_ _atom_type_symbol _atom_type_oxidation_number _atom_type_number_in_cell _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0 140 0.018 0.009 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; H 0 176 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; O 0 40 0.049 0.032 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; Si 0 4 0.254 0.330 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_calc_attached_atom Si1 0.18570(10) 0.41928(5) 0.3801(2) 0.000773(5) 1.000 . Uani d ? O1 0.0734(2) 0.32860(10) 0.3537(3) 0.00059(1) 1.000 . Uani d ? O2 0.2103(2) 0.27010(10) 0.2392(3) 0.00057(1) 1.000 . Uani d ? O3 0.1204(2) 0.18770(10) 0.1557(4) 0.00068(1) 1.000 . Uani d ? O4 0.6244(2) 0.22900(10) 0.3912(4) 0.00082(1) 1.000 . Uani d ? O5 0.2104(3) 0.42150(10) 0.0617(4) 0.00086(1) 1.000 . Uani d ? O6 0.1235(3) 0.14690(10) 0.3812(5) 0.00110(1) 1.000 . Uani d ? O7 0.2091(3) 0.07380(10) 0.2440(5) 0.00101(1) 1.000 . Uani d ? O8 0.3343(4) 0.1121(2) 0.3097(9) 0.00184(3) 1.000 . Uani d ? O9 -0.1372(4) 0.3639(2) 0.2477(9) 0.00201(4) 1.000 . Uani d ? O10 -0.0479(3) 0.39540(10) 0.0774(7) 0.00127(3) 1.000 . Uani d ? C1 0.0768(3) 0.31860(10) 0.1902(5) 0.00049(1) 1.000 . Uani d ? C2 0.1242(3) 0.2707(2) 0.1624(5) 0.00051(1) 1.000 . Uani d ? C3 0.0726(3) 0.2279(2) 0.2228(5) 0.00056(1) 1.000 . Uani d ? C4 -0.0252(3) 0.2272(2) 0.1685(6) 0.00070(1) 1.000 . Uani d ? C5 -0.0707(3) 0.2733(2) 0.2067(6) 0.00070(1) 1.000 . Uani d ? C6 -0.0226(3) 0.3156(2) 0.1330(6) 0.00063(1) 1.000 . Uani d ? C7 0.1282(3) 0.35760(10) 0.1100(5) 0.00054(1) 1.000 . Uani d ? C8 0.1446(4) 0.3605(2) -0.0539(6) 0.00071(1) 1.000 . Uani d ? C9 0.1940(5) 0.3994(2) -0.0760(6) 0.00094(3) 1.000 . Uani d ? C10 0.1683(3) 0.3949(2) 0.1779(5) 0.00061(1) 1.000 . Uani d ? C11 0.0791(5) 0.4297(2) 0.4896(8) 0.00105(3) 1.000 . Uani d ? C12 0.2628(5) 0.3797(2) 0.4918(7) 0.00119(3) 1.000 . Uani d ? C13 0.2420(5) 0.4778(2) 0.3461(8) 0.00120(3) 1.000 . Uani d ? C14 0.2857(3) 0.2818(2) 0.1444(7) 0.00092(3) 1.000 . Uani d ? C15 0.3724(3) 0.2691(2) 0.2231(6) 0.00068(1) 1.000 . Uani d ? C16 0.3899(3) 0.2233(2) 0.2723(6) 0.00070(1) 1.000 . Uani d ? C17 0.4744(3) 0.2110(2) 0.3310(6) 0.00066(1) 1.000 . Uani d ? C18 0.5416(3) 0.2444(2) 0.3367(6) 0.00063(1) 1.000 . Uani d ? C19 0.5252(4) 0.2904(2) 0.2930(6) 0.00071(1) 1.000 . Uani d ? C20 0.4395(4) 0.3022(2) 0.2364(6) 0.00076(3) 1.000 . Uani d ? C21 0.7008(4) 0.2598(2) 0.3749(8) 0.00100(3) 1.000 . Uani d ? C22 0.1397(4) 0.1505(2) 0.2457(7) 0.00073(3) 1.000 . Uani d ? C23 0.1847(4) 0.1127(2) 0.1467(7) 0.00081(3) 1.000 . Uani d ? C24 0.1221(4) 0.0951(2) 0.0213(7) 0.00081(3) 1.000 . Uani d ? C25 0.0401(5) 0.0744(2) 0.0576(8) 0.00104(3) 1.000 . Uani d ? C26 -0.0195(5) 0.0604(3) -0.0590(10) 0.00134(4) 1.000 . Uani d ? C27 0.0045(7) 0.0656(3) -0.2130(10) 0.00136(4) 1.000 . Uani d ? C28 0.0840(6) 0.0849(3) -0.2526(9) 0.00125(4) 1.000 . Uani d ? C29 0.1447(4) 0.1004(2) -0.1372(8) 0.00096(3) 1.000 . Uani d ? C30 0.3021(6) 0.0388(3) 0.4330(10) 0.00155(4) 1.000 . Uani d ? C31 -0.0757(4) 0.3601(2) 0.1579(8) 0.00090(3) 1.000 . Uani d ? C32 0.2883(5) 0.0787(2) 0.3221(10) 0.00120(3) 1.000 . Uani d ? C33 -0.0910(5) 0.4406(2) 0.0970(10) 0.00160(4) 1.000 . Uani d ? C34 -0.0345(7) 0.4761(3) 0.029(2) 0.00223(6) 1.000 . Uani d ? C35 -0.0761(4) 0.1849(2) 0.2390(9) 0.00105(3) 1.000 . Uani d ? H1 0.1039 0.3008 0.4065 0.001 1.000 . Uiso c ? H2 0.1336 0.2669 0.0533 0.001 1.000 . Uiso c ? H3 0.0754 0.2269 0.3337 0.001 1.000 . Uiso c ? H4 -0.0255 0.2236 0.0581 0.001 1.000 . Uiso c ? H6 -0.0210 0.3101 0.0237 0.001 1.000 . Uiso c ? H8 0.1242 0.3390 -0.1317 0.001 1.000 . Uiso c ? H9 0.2149 0.4101 -0.1745 0.001 1.000 . Uiso c ? H16 0.3438 0.2000 0.2653 0.001 1.000 . Uiso c ? H17 0.4855 0.1798 0.3670 0.001 1.000 . Uiso c ? H19 0.5711 0.3138 0.3007 0.001 1.000 . Uiso c ? H20 0.4271 0.3339 0.2064 0.001 1.000 . Uiso c ? H23 0.2377 0.1254 0.1001 0.001 1.000 . Uiso c ? H25 0.0245 0.0696 0.1643 0.001 1.000 . Uiso c ? H26 -0.0771 0.0476 -0.0334 0.002 1.000 . Uiso c ? H27 -0.0352 0.0548 -0.2921 0.002 1.000 . Uiso c ? H28 0.0992 0.0882 -0.3594 0.002 1.000 . Uiso c ? H29 0.2006 0.1147 -0.1665 0.001 1.000 . Uiso c ? H51 -0.0713 0.2771 0.3170 0.001 1.000 . Uiso c ? H52 -0.1313 0.2721 0.1694 0.001 1.000 . Uiso c ? H111 0.0403 0.4493 0.4293 0.001 1.000 . Uiso c ? H112 0.0926 0.4451 0.5857 0.001 1.000 . Uiso c ? H113 0.0503 0.4005 0.5098 0.001 1.000 . Uiso c ? H121 0.2365 0.3490 0.4981 0.001 1.000 . Uiso c ? H122 0.2711 0.3919 0.5938 0.001 1.000 . Uiso c ? H123 0.3192 0.3777 0.4399 0.001 1.000 . Uiso c ? H131 0.2971 0.4730 0.2902 0.001 1.000 . Uiso c ? H132 0.2538 0.4928 0.4417 0.001 1.000 . Uiso c ? H133 0.2030 0.4972 0.2839 0.001 1.000 . Uiso c ? H141 0.2852 0.3148 0.1239 0.001 1.000 . Uiso c ? H142 0.2816 0.2650 0.0486 0.001 1.000 . Uiso c ? H211 0.7536 0.2445 0.4133 0.001 1.000 . Uiso c ? H212 0.6908 0.2880 0.4321 0.001 1.000 . Uiso c ? H213 0.7093 0.2674 0.2675 0.001 1.000 . Uiso c ? H301 0.2577 0.0150 0.4148 0.002 1.000 . Uiso c ? H302 0.2958 0.0499 0.5378 0.002 1.000 . Uiso c ? H303 0.3605 0.0258 0.4197 0.002 1.000 . Uiso c ? H331 -0.0984 0.4469 0.2055 0.002 1.000 . Uiso c ? H332 -0.1482 0.4406 0.0476 0.002 1.000 . Uiso c ? H341 -0.0237 0.4686 -0.0774 0.003 1.000 . Uiso c ? H342 0.0211 0.4776 0.0836 0.003 1.000 . Uiso c ? H343 -0.0642 0.5059 0.0353 0.003 1.000 . Uiso c ? H351 -0.1367 0.1846 0.2019 0.001 1.000 . Uiso c ? H352 -0.0767 0.1877 0.3501 0.001 1.000 . Uiso c ? H353 -0.0469 0.1564 0.2106 0.001 1.000 . Uiso c ? loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Si1 0.0721(9) 0.0574(7) 0.0536(8) -0.0074(7) 0.0013(8) -0.0127(7) O1 0.048(2) 0.054(2) 0.038(2) 0.003(2) 0.003(2) 0.0000(10) O2 0.035(2) 0.059(2) 0.041(2) 0.000(2) 0.0040(10) 0.004(2) O3 0.067(2) 0.0420(10) 0.053(2) 0.0040(10) 0.001(2) -0.004(2) O4 0.045(2) 0.085(2) 0.066(2) 0.005(2) -0.006(2) 0.011(2) O5 0.087(3) 0.062(2) 0.055(2) -0.022(2) 0.006(2) 0.004(2) O6 0.116(3) 0.078(2) 0.067(3) 0.023(2) 0.008(3) 0.013(2) O7 0.074(2) 0.052(2) 0.113(3) 0.002(2) -0.019(3) 0.011(2) O8 0.118(4) 0.110(4) 0.208(7) -0.030(3) -0.070(5) 0.043(4) O9 0.126(4) 0.122(4) 0.229(7) 0.068(4) 0.099(5) 0.055(5) O10 0.082(3) 0.065(2) 0.153(5) 0.019(2) 0.022(3) 0.034(3) C1 0.040(2) 0.046(2) 0.031(2) -0.001(2) -0.001(2) -0.004(2) C2 0.040(2) 0.047(2) 0.035(2) 0.000(2) 0.000(2) 0.000(2) C3 0.044(2) 0.046(2) 0.042(2) 0.002(2) 0.001(2) -0.003(2) C4 0.054(3) 0.056(2) 0.055(3) -0.018(3) -0.007(3) -0.003(2) C5 0.039(2) 0.064(3) 0.062(3) -0.008(2) -0.005(3) 0.004(3) C6 0.038(2) 0.059(2) 0.052(3) 0.001(2) -0.008(2) 0.000(2) C7 0.042(2) 0.046(2) 0.040(2) 0.003(2) 0.002(2) 0.004(2) C8 0.071(3) 0.057(3) 0.039(2) -0.004(3) 0.002(3) 0.001(2) C9 0.100(5) 0.072(3) 0.049(3) -0.023(4) 0.006(3) 0.003(3) C10 0.052(3) 0.046(2) 0.046(3) -0.009(2) 0.002(2) 0.005(2) C11 0.096(5) 0.070(3) 0.083(4) 0.004(3) 0.017(4) -0.020(3) C12 0.094(5) 0.121(5) 0.066(4) 0.012(4) -0.015(4) -0.018(4) C13 0.116(5) 0.075(3) 0.092(5) -0.033(4) 0.006(5) -0.022(4) C14 0.044(3) 0.105(4) 0.070(4) 0.005(3) 0.007(3) 0.032(3) C15 0.041(3) 0.076(3) 0.045(3) 0.002(3) 0.008(2) 0.010(3) C16 0.040(3) 0.069(3) 0.057(3) -0.007(2) 0.004(2) 0.004(3) C17 0.043(3) 0.058(3) 0.055(3) 0.003(2) 0.000(3) 0.000(2) C18 0.041(3) 0.073(3) 0.036(2) 0.000(2) 0.004(2) 0.000(2) C19 0.054(3) 0.052(2) 0.062(3) -0.010(2) 0.003(3) 0.003(3) C20 0.061(3) 0.061(3) 0.059(3) 0.001(3) 0.008(3) 0.012(3) C21 0.044(3) 0.116(4) 0.077(4) -0.015(3) 0.006(3) 0.011(4) C22 0.054(3) 0.052(3) 0.068(3) 0.000(2) -0.001(3) 0.000(3) C23 0.062(3) 0.047(2) 0.084(4) 0.001(2) 0.002(3) 0.006(3) C24 0.076(4) 0.039(2) 0.076(4) 0.006(3) 0.006(3) -0.008(3) C25 0.087(4) 0.064(3) 0.094(5) -0.016(3) 0.000(4) -0.009(4) C26 0.082(5) 0.080(4) 0.157(8) -0.011(4) -0.006(6) -0.021(5) C27 0.118(7) 0.091(5) 0.113(7) -0.009(5) -0.023(6) -0.017(5) C28 0.131(7) 0.086(5) 0.080(5) 0.029(5) -0.012(5) -0.005(4) C29 0.081(4) 0.063(3) 0.085(4) 0.015(3) 0.012(4) 0.002(3) C30 0.132(7) 0.104(5) 0.130(7) 0.023(5) -0.040(6) 0.016(5) C31 0.055(3) 0.072(3) 0.086(4) 0.012(3) -0.010(4) 0.014(3) C32 0.092(5) 0.068(4) 0.123(6) 0.009(4) -0.028(5) 0.002(4) C33 0.090(5) 0.077(4) 0.21(1) 0.024(4) 0.008(7) 0.045(6) C34 0.141(8) 0.088(5) 0.30(1) 0.016(5) 0.03(1) 0.067(8) C35 0.058(3) 0.069(3) 0.121(6) -0.019(3) -0.004(4) 0.003(4) #------------------------------------------------------------------------------ _refine_special_details ; ? ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme 'w = 1/[\s^2^(Fo) + 0.00022|Fo|^2^]' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2565 _refine_ls_number_parameters 415 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all ? _refine_ls_R_factor_obs 0.0484 _refine_ls_wR_factor_all ? _refine_ls_wR_factor_obs 0.0602 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 2.173 _refine_ls_shift/esd_max 0.0050 _refine_ls_shift/esd_mean 0.0000 _refine_diff_density_min -0.19 _refine_diff_density_max 0.21 #------------------------------------------------------------------------------ _geom_special_details ; ? ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag SI1 C10 1.882(5) . . yes SI1 C11 1.858(7) . . yes SI1 C12 1.863(7) . . yes SI1 C13 1.877(6) . . yes O1 C1 1.430(5) . . yes O1 H1 1.01 . . no O2 C2 1.434(5) . . yes O2 C14 1.419(6) . . yes O3 C3 1.458(6) . . yes O3 C22 1.336(7) . . yes O4 C18 1.381(6) . . yes O4 C21 1.434(7) . . yes O5 C9 1.357(6) . . yes O5 C10 1.395(6) . . yes O6 C22 1.190(7) . . yes O7 C23 1.427(7) . . yes O7 C32 1.356(9) . . yes O8 C32 1.169(9) . . yes O9 C31 1.196(9) . . yes O10 C31 1.282(7) . . yes O10 C33 1.439(7) . . yes C1 C2 1.545(6) . . yes C1 C6 1.552(6) . . yes C1 C7 1.506(5) . . yes C2 C3 1.522(7) . . yes C2 H2 0.95 . . no C3 C4 1.520(6) . . yes C3 H3 0.95 . . no C4 C5 1.504(8) . . yes C4 C35 1.538(8) . . yes C4 H4 0.95 . . no C5 C6 1.529(8) . . yes C5 H51 0.95 . . no C5 H52 0.95 . . no C6 C31 1.500(8) . . yes C6 H6 0.95 . . no C7 C8 1.427(7) . . yes C7 C10 1.343(6) . . yes C8 C9 1.335(9) . . yes C8 H8 0.95 . . no C9 H9 0.95 . . no C11 H111 0.95 . . no C11 H112 0.95 . . no C11 H113 0.95 . . no C12 H121 0.95 . . no C12 H122 0.95 . . no C12 H123 0.95 . . no C13 H131 0.95 . . no C13 H132 0.94 . . no C13 H133 0.96 . . no C14 C15 1.493(7) . . yes C14 H141 0.95 . . no C14 H142 0.95 . . no C15 C16 1.387(8) . . yes C15 C20 1.370(8) . . yes C16 C17 1.391(7) . . yes C16 H16 0.95 . . no C17 C18 1.373(7) . . yes C17 H17 0.95 . . no C18 C19 1.376(8) . . yes C19 C20 1.398(8) . . yes C19 H19 0.95 . . no C20 H20 0.95 . . no C21 H211 0.95 . . no C21 H212 0.95 . . no C21 H213 0.95 . . no C22 C23 1.519(8) . . yes C23 C24 1.503(8) . . yes C23 H23 0.95 . . no C24 C25 1.382(9) . . yes C24 C29 1.406(9) . . yes C25 C26 1.39(1) . . yes C25 H25 0.95 . . no C26 C27 1.37(1) . . yes C26 H26 0.95 . . no C27 C28 1.34(1) . . yes C27 H27 0.95 . . no C28 C29 1.41(1) . . yes C28 H28 0.95 . . no C29 H29 0.95 . . no C30 C32 1.49(1) . . yes C30 H301 0.95 . . no C30 H302 0.96 . . no C30 H303 0.95 . . no C33 C34 1.43(1) . . yes C33 H331 0.95 . . no C33 H332 0.95 . . no C34 H341 0.95 . . no C34 H342 0.95 . . no C34 H343 0.95 . . no C35 H351 0.95 . . no C35 H352 0.96 . . no C35 H353 0.95 . . no #------------------------------------------------------------------------------ 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 SI1 C11 114.0(3) . . . yes C10 SI1 C12 109.6(3) . . . yes C10 SI1 C13 104.0(3) . . . yes C11 SI1 C12 110.8(3) . . . yes C11 SI1 C13 108.4(3) . . . yes C12 SI1 C13 109.8(3) . . . yes C1 O1 H1 105.5 . . . no C2 O2 C14 115.7(3) . . . yes C3 O3 C22 119.4(4) . . . yes C18 O4 C21 118.3(4) . . . yes C9 O5 C10 107.0(4) . . . yes C23 O7 C32 115.3(4) . . . yes C31 O10 C33 119.2(6) . . . yes O1 C1 C2 109.9(3) . . . yes O1 C1 C6 106.7(4) . . . yes O1 C1 C7 108.6(3) . . . yes C2 C1 C6 109.5(3) . . . yes C2 C1 C7 110.1(4) . . . yes C6 C1 C7 112.0(4) . . . yes O2 C2 C1 110.1(4) . . . yes O2 C2 C3 106.3(4) . . . yes O2 C2 H2 108.7 . . . no C1 C2 C3 114.7(4) . . . yes C1 C2 H2 108.5 . . . no C3 C2 H2 108.5 . . . no O3 C3 C2 104.1(3) . . . yes O3 C3 C4 109.3(4) . . . yes O3 C3 H3 110.5 . . . no C2 C3 C4 112.6(4) . . . yes C2 C3 H3 110.0 . . . no C4 C3 H3 110.3 . . . no C3 C4 C5 110.4(4) . . . yes C3 C4 C35 110.9(4) . . . yes C3 C4 H4 108.1 . . . no C5 C4 C35 111.8(4) . . . yes C5 C4 H4 107.9 . . . no C35 C4 H4 107.7 . . . no C4 C5 C6 112.4(4) . . . yes C4 C5 H51 108.6 . . . no C4 C5 H52 108.5 . . . no C6 C5 H51 109.0 . . . no C6 C5 H52 109.1 . . . no H51 C5 H52 109.2 . . . no C1 C6 C5 110.7(4) . . . yes C1 C6 C31 113.9(4) . . . yes C1 C6 H6 107.3 . . . no C5 C6 C31 110.8(4) . . . yes C5 C6 H6 106.9 . . . no C31 C6 H6 106.9 . . . no C1 C7 C8 125.2(4) . . . yes C1 C7 C10 127.0(4) . . . yes C8 C7 C10 107.8(4) . . . yes C7 C8 C9 106.3(4) . . . yes C7 C8 H8 126.8 . . . no C9 C8 H8 127.0 . . . no O5 C9 C8 110.8(5) . . . yes O5 C9 H9 124.6 . . . no C8 C9 H9 124.6 . . . no SI1 C10 O5 113.4(3) . . . yes SI1 C10 C7 138.3(4) . . . yes O5 C10 C7 108.2(4) . . . yes SI1 C11 H111 109.3 . . . no SI1 C11 H112 109.3 . . . no SI1 C11 H113 109.6 . . . no H111 C11 H112 109.2 . . . no H111 C11 H113 109.7 . . . no H112 C11 H113 109.6 . . . no SI1 C12 H121 109.1 . . . no SI1 C12 H122 109.5 . . . no SI1 C12 H123 109.5 . . . no H121 C12 H122 109.4 . . . no H121 C12 H123 109.4 . . . no H122 C12 H123 109.9 . . . no SI1 C13 H131 109.3 . . . no SI1 C13 H132 110.3 . . . no SI1 C13 H133 109.0 . . . no H131 C13 H132 110.1 . . . no H131 C13 H133 108.4 . . . no H132 C13 H133 109.8 . . . no O2 C14 C15 111.1(4) . . . yes O2 C14 H141 109.2 . . . no O2 C14 H142 109.1 . . . no C15 C14 H141 109.1 . . . no C15 C14 H142 108.9 . . . no H141 C14 H142 109.4 . . . no C14 C15 C16 121.5(5) . . . yes C14 C15 C20 119.7(5) . . . yes C16 C15 C20 118.6(4) . . . yes C15 C16 C17 120.7(5) . . . yes C15 C16 H16 119.7 . . . no C17 C16 H16 119.6 . . . no C16 C17 C18 119.4(5) . . . yes C16 C17 H17 120.4 . . . no C18 C17 H17 120.2 . . . no O4 C18 C17 115.9(5) . . . yes O4 C18 C19 123.1(5) . . . yes C17 C18 C19 120.9(5) . . . yes C18 C19 C20 118.7(5) . . . yes C18 C19 H19 120.9 . . . no C20 C19 H19 120.4 . . . no C15 C20 C19 121.5(5) . . . yes C15 C20 H20 118.9 . . . no C19 C20 H20 119.6 . . . no O4 C21 H211 109.7 . . . no O4 C21 H212 109.8 . . . no O4 C21 H213 109.6 . . . no H211 C21 H212 109.4 . . . no H211 C21 H213 109.2 . . . no H212 C21 H213 109.2 . . . no O3 C22 O6 126.0(5) . . . yes O3 C22 C23 109.1(5) . . . yes O6 C22 C23 124.9(5) . . . yes O7 C23 C22 109.1(5) . . . yes O7 C23 C24 108.5(4) . . . yes O7 C23 H23 109.2 . . . no C22 C23 C24 111.3(5) . . . yes C22 C23 H23 109.3 . . . no C24 C23 H23 109.5 . . . no C23 C24 C25 121.3(6) . . . yes C23 C24 C29 120.5(5) . . . yes C25 C24 C29 118.1(6) . . . yes C24 C25 C26 121.0(6) . . . yes C24 C25 H25 119.3 . . . no C26 C25 H25 119.7 . . . no C25 C26 C27 119.7(7) . . . yes C25 C26 H26 120.7 . . . no C27 C26 H26 119.6 . . . no C26 C27 C28 120.9(8) . . . yes C26 C27 H27 119.5 . . . no C28 C27 H27 119.6 . . . no C27 C28 C29 120.6(7) . . . yes C27 C28 H28 119.5 . . . no C29 C28 H28 119.8 . . . no C24 C29 C28 119.6(6) . . . yes C24 C29 H29 120.3 . . . no C28 C29 H29 120.1 . . . no C32 C30 H301 109.7 . . . no C32 C30 H302 109.7 . . . no C32 C30 H303 110.1 . . . no H301 C30 H302 108.6 . . . no H301 C30 H303 109.5 . . . no H302 C30 H303 109.3 . . . no O9 C31 O10 121.3(6) . . . yes O9 C31 C6 124.4(6) . . . yes O10 C31 C6 114.2(5) . . . yes O7 C32 O8 122.7(7) . . . yes O7 C32 C30 110.8(6) . . . yes O8 C32 C30 126.2(8) . . . yes O10 C33 C34 108.5(7) . . . yes O10 C33 H331 109.3 . . . no O10 C33 H332 110.1 . . . no C34 C33 H331 109.4 . . . no C34 C33 H332 109.9 . . . no H331 C33 H332 109.5 . . . no C33 C34 H341 109.4 . . . no C33 C34 H342 109.7 . . . no C33 C34 H343 109.2 . . . no H341 C34 H342 109.8 . . . no H341 C34 H343 109.3 . . . no H342 C34 H343 109.4 . . . no C4 C35 H351 109.7 . . . no C4 C35 H352 109.4 . . . no C4 C35 H353 109.8 . . . no H351 C35 H352 109.0 . . . no H351 C35 H353 109.7 . . . no H352 C35 H353 109.3 . . . no #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 O4 2.829(4) . 3_456 no O1 C17 3.270(6) . 3_456 no #------------------------------------------------------------------------------ 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 SI1 C10 O5 C9 . . . . 178.6(4) no SI1 C10 C7 C1 . . . . 0.6(8) no SI1 C10 C7 C8 . . . . -178.0(5) no O1 C1 C2 O2 . . . . -52.9(4) no O1 C1 C2 C3 . . . . 66.9(4) no O1 C1 C6 C5 . . . . -65.8(4) no O1 C1 C6 C31 . . . . 59.8(5) no O1 C1 C7 C8 . . . . -179.0(4) no O1 C1 C7 C10 . . . . 2.7(6) no O2 C2 C1 C6 . . . . -169.7(3) no O2 C2 C1 C7 . . . . 66.7(4) no O2 C2 C3 O3 . . . . -69.4(4) no O2 C2 C3 C4 . . . . 172.3(4) no O2 C14 C15 C16 . . . . 57.0(7) no O2 C14 C15 C20 . . . . -128.4(5) no O3 C3 C2 C1 . . . . 168.8(3) no O3 C3 C4 C5 . . . . -167.8(4) no O3 C3 C4 C35 . . . . 67.8(5) no O3 C22 C23 O7 . . . . 177.4(4) no O3 C22 C23 C24 . . . . -62.9(6) no O4 C18 C17 C16 . . . . -177.8(4) no O4 C18 C19 C20 . . . . 178.7(5) no O5 C9 C8 C7 . . . . 0.1(7) no O5 C10 SI1 C11 . . . . 125.9(4) no O5 C10 SI1 C12 . . . . -109.2(4) no O5 C10 SI1 C13 . . . . 8.1(4) no O5 C10 C7 C1 . . . . 178.3(4) no O5 C10 C7 C8 . . . . -0.3(5) no O6 C22 O3 C3 . . . . -2.1(8) no O6 C22 C23 O7 . . . . -3.5(8) no O6 C22 C23 C24 . . . . 116.2(7) no O7 C23 C24 C25 . . . . 60.3(7) no O7 C23 C24 C29 . . . . -121.3(6) no O8 C32 O7 C23 . . . . 0(1) no O9 C31 O10 C33 . . . . 0(1) no O9 C31 C6 C1 . . . . -112.1(7) no O9 C31 C6 C5 . . . . 13.5(9) no O10 C31 C6 C1 . . . . 65.7(7) no O10 C31 C6 C5 . . . . -168.7(5) no C1 C2 O2 C14 . . . . -96.2(4) no C1 C2 C3 C4 . . . . 50.5(5) no C1 C6 C5 C4 . . . . -59.2(5) no C1 C7 C8 C9 . . . . -178.5(5) no C2 O2 C14 C15 . . . . -166.4(4) no C2 C1 C6 C5 . . . . 53.1(5) no C2 C1 C6 C31 . . . . 178.7(4) no C2 C1 C7 C8 . . . . 60.6(6) no C2 C1 C7 C10 . . . . -117.7(5) no C2 C3 O3 C22 . . . . 134.9(4) no C2 C3 C4 C5 . . . . -52.6(5) no C2 C3 C4 C35 . . . . -177.0(4) no C3 O3 C22 C23 . . . . 177.0(4) no C3 C2 O2 C14 . . . . 139.0(4) no C3 C2 C1 C6 . . . . -50.0(5) no C3 C2 C1 C7 . . . . -173.5(4) no C3 C4 C5 C6 . . . . 58.0(5) no C4 C3 O3 C22 . . . . -104.6(5) no C4 C5 C6 C31 . . . . 173.4(4) no C5 C6 C1 C7 . . . . 175.5(4) no C6 C1 C7 C8 . . . . -61.4(6) no C6 C1 C7 C10 . . . . 120.2(5) no C6 C5 C4 C35 . . . . -178.2(5) no C6 C31 O10 C33 . . . . -177.1(5) no C7 C1 C6 C31 . . . . -58.9(5) no C7 C10 SI1 C11 . . . . -56.5(6) no C7 C10 SI1 C12 . . . . 68.4(6) no C7 C10 SI1 C13 . . . . -174.3(6) no C7 C10 O5 C9 . . . . 0.3(6) no C8 C9 O5 C10 . . . . -0.3(7) no C9 C8 C7 C10 . . . . 0.2(6) no C14 C15 C16 C17 . . . . 173.4(5) no C14 C15 C20 C19 . . . . -172.6(5) no C15 C16 C17 C18 . . . . -1.5(8) no C15 C20 C19 C18 . . . . -0.3(8) no C16 C15 C20 C19 . . . . 2.2(8) no C16 C17 C18 C19 . . . . 3.5(8) no C17 C16 C15 C20 . . . . -1.3(8) no C17 C18 O4 C21 . . . . 169.5(5) no C17 C18 C19 C20 . . . . -2.6(8) no C19 C18 O4 C21 . . . . -11.8(7) no C22 C23 O7 C32 . . . . -82.7(6) no C22 C23 C24 C25 . . . . -59.8(7) no C22 C23 C24 C29 . . . . 118.6(6) no C23 O7 C32 C30 . . . . 173.7(6) no C23 C24 C25 C26 . . . . 176.7(6) no C23 C24 C29 C28 . . . . -178.2(6) no C24 C23 O7 C32 . . . . 156.0(5) no C24 C25 C26 C27 . . . . 2(1) no C24 C29 C28 C27 . . . . 0(1) no C25 C24 C29 C28 . . . . 0.3(9) no C25 C26 C27 C28 . . . . -1(1) no C26 C25 C24 C29 . . . . -1.8(9) no C26 C27 C28 C29 . . . . 0(1) no C31 O10 C33 C34 . . . . 164.8(9) no #------------------------------------------------------------------------------ loop_ _geom_bond_atom_site_label_D _geom_bond_atom_site_label_H _geom_contact_atom_site_label_A _geom_bond_distance_DH _geom_contact_distance_HA _geom_contact_distance_DA _geom_angle_DHA _geom_contact_site_symmetry_A O1 H1 O4 1.01 1.95 2.829(4) 143.2 3_456 O1 H1 O2 1.01 2.30 2.793(4) 108.7 .