#------------------------------------------------------------------------------ #$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $ #$Revision: 176729 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/21/1502110.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1502110 loop_ _publ_author_name 'Egan, Ben A.' 'Paradowski, Michael' 'Thomas, Lynne H.' 'Marquez, Rodolfo' _publ_section_title ; Regiocontrolled rearrangement of isobenzofurans. ; _journal_issue 8 _journal_name_full 'Organic letters' _journal_page_first 2086 _journal_page_last 2089 _journal_paper_doi 10.1021/ol200498k _journal_volume 13 _journal_year 2011 _chemical_absolute_configuration rmad _chemical_formula_sum 'C22 H31 N O5 Si' _chemical_formula_weight 417.57 _chemical_name_systematic ; ? ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2010-09-13T15:39:52-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.7398(3) _cell_length_b 8.2057(2) _cell_length_c 25.4880(9) _cell_measurement_reflns_used 6688 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 62.5231 _cell_measurement_theta_min 3.4652 _cell_volume 2246.20(11) _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 10.4383 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0298049 _diffrn_orient_matrix_UB_12 -0.1026245 _diffrn_orient_matrix_UB_13 -0.0410969 _diffrn_orient_matrix_UB_21 0.1177362 _diffrn_orient_matrix_UB_22 0.0869027 _diffrn_orient_matrix_UB_23 -0.0295196 _diffrn_orient_matrix_UB_31 0.1431916 _diffrn_orient_matrix_UB_32 -0.0501197 _diffrn_orient_matrix_UB_33 0.0329979 _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_unetI/netI 0.045 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 14532 _diffrn_reflns_theta_full 61.99 _diffrn_reflns_theta_max 61.99 _diffrn_reflns_theta_min 3.47 _exptl_absorpt_coefficient_mu 1.186 _exptl_absorpt_correction_T_max 0.905 _exptl_absorpt_correction_T_min 0.846 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.212 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.04 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.06 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 270 _refine_ls_number_reflns 3524 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.06 _refine_ls_R_factor_all 0.0534 _refine_ls_R_factor_gt 0.0391 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0434P)^2^+0.3129P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0854 _refine_ls_wR_factor_ref 0.0919 _reflns_number_gt 2907 _reflns_number_total 3524 _reflns_threshold_expression >2\s(I) _cod_data_source_file ol200498k_si_006.cif _cod_data_source_block be415b _cod_original_sg_symbol_H-M P212121 _cod_database_code 1502110 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' 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 Si1 Si -1.35272(7) -0.55876(9) -1.46462(3) 0.03364(19) Uani 1 1 d . O1 O -0.5067(2) -0.8219(3) -1.28893(9) 0.0569(6) Uani 1 1 d . O2 O -1.04819(17) -0.4028(3) -1.25261(7) 0.0425(5) Uani 1 1 d . H52 H -1.1156 -0.3715 -1.2393 0.064 Uiso 1 1 calc R O3 O -1.03361(16) -0.5732(2) -1.34836(8) 0.0394(5) Uani 1 1 d . O4 O -1.21989(19) -0.6816(2) -1.35758(9) 0.0496(6) Uani 1 1 d . O5 O -1.38981(16) -0.4649(2) -1.40831(7) 0.0332(4) Uani 1 1 d . N1 N -0.7128(2) -0.8305(3) -1.28994(10) 0.0447(6) Uani 1 1 d . C1 C -0.6119(3) -0.8905(4) -1.27094(13) 0.0531(9) Uani 1 1 d . H1 H -0.6117 -0.9768 -1.2461 0.064 Uiso 1 1 calc R C2 C -0.5480(3) -0.7066(4) -1.32393(12) 0.0441(8) Uani 1 1 d . H2 H -0.4966 -0.6364 -1.3442 0.053 Uiso 1 1 calc R C3 C -0.6724(3) -0.7094(4) -1.32485(11) 0.0366(7) Uani 1 1 d . C4 C -0.7656(3) -0.6055(3) -1.35188(11) 0.0389(7) Uani 1 1 d . H4A H -0.8253 -0.6756 -1.371 0.047 Uiso 1 1 calc R H4B H -0.7229 -0.5353 -1.3778 0.047 Uiso 1 1 calc R C5 C -0.8369(3) -0.4980(3) -1.31260(10) 0.0331(7) Uani 1 1 d . H5 H -0.8602 -0.5678 -1.282 0.04 Uiso 1 1 calc R C6 C -0.7552(3) -0.3593(4) -1.29218(13) 0.0465(8) Uani 1 1 d . H6A H -0.7423 -0.2791 -1.3201 0.07 Uiso 1 1 calc R H6B H -0.6746 -0.4031 -1.281 0.07 Uiso 1 1 calc R H6C H -0.7963 -0.3068 -1.2623 0.07 Uiso 1 1 calc R C7 C -0.9561(2) -0.4314(3) -1.33620(10) 0.0326(6) Uani 1 1 d . H7 H -0.9359 -0.3726 -1.3695 0.039 Uiso 1 1 calc R C8 C -1.0272(3) -0.3184(4) -1.30035(10) 0.0349(7) Uani 1 1 d . H8 H -0.9759 -0.2191 -1.2933 0.042 Uiso 1 1 calc R C9 C -1.1589(3) -0.5586(3) -1.35395(11) 0.0359(6) Uani 1 1 d . C10 C -1.2110(2) -0.3911(3) -1.35470(11) 0.0319(6) Uani 1 1 d . C11 C -1.1458(3) -0.2692(3) -1.32741(10) 0.0319(6) Uani 1 1 d . C12 C -1.1923(3) -0.1127(3) -1.32532(11) 0.0362(7) Uani 1 1 d . H12 H -1.145 -0.028 -1.3096 0.043 Uiso 1 1 calc R C13 C -1.3086(3) -0.0802(3) -1.34640(10) 0.0351(7) Uani 1 1 d . H13 H -1.3419 0.0265 -1.343 0.042 Uiso 1 1 calc R C14 C -1.3781(2) -0.1980(3) -1.37227(11) 0.0331(7) Uani 1 1 d . C15 C -1.5081(3) -0.1603(4) -1.39189(12) 0.0398(7) Uani 1 1 d . H15A H -1.5408 -0.0651 -1.3732 0.06 Uiso 1 1 calc R H15B H -1.5624 -0.2542 -1.3856 0.06 Uiso 1 1 calc R H15C H -1.5051 -0.1371 -1.4296 0.06 Uiso 1 1 calc R C16 C -1.3249(3) -0.3527(3) -1.37882(10) 0.0322(6) Uani 1 1 d . C17 C -1.1855(3) -0.5328(4) -1.48028(12) 0.0480(8) Uani 1 1 d . H17A H -1.1618 -0.4186 -1.4752 0.072 Uiso 1 1 calc R H17B H -1.1706 -0.564 -1.5169 0.072 Uiso 1 1 calc R H17C H -1.1356 -0.6022 -1.4571 0.072 Uiso 1 1 calc R C18 C -1.3955(3) -0.7766(3) -1.45638(13) 0.0475(8) Uani 1 1 d . H18A H -1.3408 -0.8268 -1.4302 0.071 Uiso 1 1 calc R H18B H -1.3861 -0.8334 -1.49 0.071 Uiso 1 1 calc R H18C H -1.4822 -0.7845 -1.4447 0.071 Uiso 1 1 calc R C19 C -1.4470(3) -0.4623(4) -1.51848(11) 0.0408(7) Uani 1 1 d . C20 C -1.4306(3) -0.5544(5) -1.57026(13) 0.0628(10) Uani 1 1 d . H20A H -1.4595 -0.6669 -1.566 0.094 Uiso 1 1 calc R H20B H -1.3424 -0.5545 -1.5801 0.094 Uiso 1 1 calc R H20C H -1.4794 -0.5007 -1.5978 0.094 Uiso 1 1 calc R C21 C -1.4028(3) -0.2854(4) -1.52705(13) 0.0558(9) Uani 1 1 d . H21A H -1.3188 -0.2861 -1.542 0.084 Uiso 1 1 calc R H21B H -1.4017 -0.2278 -1.4934 0.084 Uiso 1 1 calc R H21C H -1.4598 -0.23 -1.5512 0.084 Uiso 1 1 calc R C22 C -1.5866(3) -0.4623(4) -1.50450(13) 0.0522(9) Uani 1 1 d . H22A H -1.6339 -0.411 -1.5329 0.078 Uiso 1 1 calc R H22B H -1.5995 -0.4011 -1.4719 0.078 Uiso 1 1 calc R H22C H -1.6151 -0.5747 -1.4997 0.078 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 Si1 0.0331(4) 0.0306(4) 0.0372(4) -0.0013(4) -0.0008(3) -0.0001(3) O1 0.0416(13) 0.0728(16) 0.0563(14) -0.0082(13) -0.0019(11) 0.0195(13) O2 0.0434(12) 0.0504(14) 0.0338(11) 0.0037(10) 0.0001(9) 0.0108(10) O3 0.0366(11) 0.0309(11) 0.0508(12) -0.0066(10) -0.0102(9) 0.0033(9) O4 0.0458(13) 0.0284(12) 0.0746(16) 0.0030(11) -0.0181(11) -0.0031(10) O5 0.0308(9) 0.0304(10) 0.0384(10) -0.0008(9) -0.0028(8) -0.0021(8) N1 0.0411(15) 0.0462(15) 0.0467(16) 0.0039(14) 0.0044(12) 0.0082(13) C1 0.054(2) 0.057(2) 0.049(2) 0.0038(16) 0.0058(17) 0.0178(18) C2 0.0389(18) 0.050(2) 0.0439(19) -0.0052(16) 0.0009(15) 0.0008(15) C3 0.0339(17) 0.0402(18) 0.0358(16) -0.0062(13) 0.0050(13) -0.0025(13) C4 0.0392(16) 0.0430(18) 0.0346(16) -0.0010(14) -0.0006(13) 0.0024(14) C5 0.0336(15) 0.0360(16) 0.0297(15) -0.0020(11) -0.0032(12) 0.0021(12) C6 0.0362(17) 0.0460(19) 0.057(2) -0.0080(16) -0.0082(15) -0.0011(15) C7 0.0375(15) 0.0293(15) 0.0311(15) 0.0007(13) -0.0023(11) -0.0064(13) C8 0.0423(17) 0.0310(16) 0.0313(15) 0.0006(13) -0.0024(12) -0.0027(13) C9 0.0384(16) 0.0317(16) 0.0375(15) -0.0004(14) -0.0085(13) 0.0004(15) C10 0.0326(15) 0.0314(16) 0.0317(15) 0.0003(12) -0.0006(12) 0.0019(12) C11 0.0367(16) 0.0287(15) 0.0304(15) 0.0023(12) -0.0037(13) 0.0050(13) C12 0.0418(17) 0.0344(16) 0.0323(16) -0.0018(13) -0.0007(13) 0.0002(13) C13 0.0447(17) 0.0276(15) 0.0329(15) 0.0001(13) 0.0030(13) 0.0073(13) C14 0.0362(17) 0.0288(16) 0.0342(15) -0.0004(13) 0.0009(12) 0.0042(13) C15 0.0378(16) 0.0357(17) 0.0459(18) -0.0002(14) 0.0010(13) 0.0075(14) C16 0.0335(15) 0.0307(15) 0.0324(15) 0.0004(12) -0.0018(12) -0.0039(13) C17 0.0424(17) 0.051(2) 0.0505(19) -0.0038(16) 0.0022(14) 0.0020(16) C18 0.0512(18) 0.0385(18) 0.053(2) -0.0063(15) -0.0064(16) -0.0057(14) C19 0.0468(18) 0.0389(17) 0.0367(16) -0.0017(14) -0.0018(13) 0.0036(15) C20 0.074(2) 0.071(2) 0.0437(19) -0.0136(19) -0.0112(17) 0.012(2) C21 0.067(2) 0.052(2) 0.048(2) 0.0148(17) 0.0046(18) 0.0089(18) C22 0.0440(18) 0.054(2) 0.058(2) -0.0109(18) -0.0162(15) 0.0083(17) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 -7 4 0.0528 0 7 -4 0.05 0 0 1 0.06 0 0 -1 0.04 5 0 8 0.0956 -5 0 -8 0.0524 -5 0 -2 0.0541 5 1 1 0.0942 0 5 11 0.0641 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle O5 Si1 C17 111.22(12) O5 Si1 C18 106.65(13) C17 Si1 C18 112.01(15) O5 Si1 C19 107.66(11) C17 Si1 C19 108.45(14) C18 Si1 C19 110.76(14) C1 O1 C2 103.8(2) C8 O2 H52 109.5 C9 O3 C7 121.0(2) C16 O5 Si1 130.82(17) C1 N1 C3 104.4(3) N1 C1 O1 114.8(3) N1 C1 H1 122.6 O1 C1 H1 122.6 C3 C2 O1 108.8(3) C3 C2 H2 125.6 O1 C2 H2 125.6 C2 C3 N1 108.1(3) C2 C3 C4 132.3(3) N1 C3 C4 119.5(2) C3 C4 C5 111.3(2) C3 C4 H4A 109.4 C5 C4 H4A 109.4 C3 C4 H4B 109.4 C5 C4 H4B 109.4 H4A C4 H4B 108 C7 C5 C6 110.6(2) C7 C5 C4 111.6(2) C6 C5 C4 111.3(2) C7 C5 H5 107.7 C6 C5 H5 107.7 C4 C5 H5 107.7 C5 C6 H6A 109.5 C5 C6 H6B 109.5 H6A C6 H6B 109.5 C5 C6 H6C 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 O3 C7 C8 109.2(2) O3 C7 C5 106.1(2) C8 C7 C5 114.1(2) O3 C7 H7 109.1 C8 C7 H7 109.1 C5 C7 H7 109.1 O2 C8 C11 112.9(2) O2 C8 C7 107.4(2) C11 C8 C7 108.4(2) O2 C8 H8 109.3 C11 C8 H8 109.3 C7 C8 H8 109.3 O4 C9 O3 118.1(3) O4 C9 C10 124.7(3) O3 C9 C10 117.2(2) C16 C10 C11 119.4(2) C16 C10 C9 122.8(2) C11 C10 C9 117.7(2) C12 C11 C10 120.1(2) C12 C11 C8 122.6(2) C10 C11 C8 117.3(2) C11 C12 C13 119.4(3) C11 C12 H12 120.3 C13 C12 H12 120.3 C12 C13 C14 122.3(3) C12 C13 H13 118.8 C14 C13 H13 118.8 C13 C14 C16 117.9(2) C13 C14 C15 120.7(2) C16 C14 C15 121.4(2) C14 C15 H15A 109.5 C14 C15 H15B 109.5 H15A C15 H15B 109.5 C14 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 O5 C16 C14 117.6(2) O5 C16 C10 122.0(2) C14 C16 C10 120.4(3) Si1 C17 H17A 109.5 Si1 C17 H17B 109.5 H17A C17 H17B 109.5 Si1 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 Si1 C18 H18A 109.5 Si1 C18 H18B 109.5 H18A C18 H18B 109.5 Si1 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C20 C19 C22 108.2(3) C20 C19 C21 107.9(3) C22 C19 C21 109.4(3) C20 C19 Si1 111.0(2) C22 C19 Si1 110.8(2) C21 C19 Si1 109.5(2) C19 C20 H20A 109.5 C19 C20 H20B 109.5 H20A C20 H20B 109.5 C19 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C19 C21 H21A 109.5 C19 C21 H21B 109.5 H21A C21 H21B 109.5 C19 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C19 C22 H22A 109.5 C19 C22 H22B 109.5 H22A C22 H22B 109.5 C19 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Si1 O5 1.6768(19) Si1 C17 1.852(3) Si1 C18 1.857(3) Si1 C19 1.881(3) O1 C1 1.343(4) O1 C2 1.374(4) O2 C8 1.418(3) O2 H52 0.84 O3 C9 1.359(3) O3 C7 1.464(3) O4 C9 1.207(3) O5 C16 1.378(3) N1 C1 1.285(4) N1 C3 1.403(4) C1 H1 0.95 C2 C3 1.336(4) C2 H2 0.95 C3 C4 1.484(4) C4 C5 1.538(4) C4 H4A 0.99 C4 H4B 0.99 C5 C7 1.517(4) C5 C6 1.529(4) C5 H5 1 C6 H6A 0.98 C6 H6B 0.98 C6 H6C 0.98 C7 C8 1.509(4) C7 H7 1 C8 C11 1.504(4) C8 H8 1 C9 C10 1.484(4) C10 C16 1.404(4) C10 C11 1.405(4) C11 C12 1.379(4) C12 C13 1.386(4) C12 H12 0.95 C13 C14 1.388(4) C13 H13 0.95 C14 C16 1.402(4) C14 C15 1.514(4) C15 H15A 0.98 C15 H15B 0.98 C15 H15C 0.98 C17 H17A 0.98 C17 H17B 0.98 C17 H17C 0.98 C18 H18A 0.98 C18 H18B 0.98 C18 H18C 0.98 C19 C20 1.531(4) C19 C22 1.540(4) C19 C21 1.542(4) C20 H20A 0.98 C20 H20B 0.98 C20 H20C 0.98 C21 H21A 0.98 C21 H21B 0.98 C21 H21C 0.98 C22 H22A 0.98 C22 H22B 0.98 C22 H22C 0.98 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 C17 Si1 O5 C16 13.3(3) C18 Si1 O5 C16 135.7(2) C19 Si1 O5 C16 -105.4(2) C3 N1 C1 O1 0.6(4) C2 O1 C1 N1 -0.9(4) C1 O1 C2 C3 0.8(3) O1 C2 C3 N1 -0.5(3) O1 C2 C3 C4 174.8(3) C1 N1 C3 C2 0.0(3) C1 N1 C3 C4 -176.1(3) C2 C3 C4 C5 -109.7(4) N1 C3 C4 C5 65.3(3) C3 C4 C5 C7 -162.6(2) C3 C4 C5 C6 73.3(3) C9 O3 C7 C8 35.2(3) C9 O3 C7 C5 158.6(2) C6 C5 C7 O3 -173.1(2) C4 C5 C7 O3 62.5(3) C6 C5 C7 C8 -52.8(3) C4 C5 C7 C8 -177.2(2) O3 C7 C8 O2 63.9(3) C5 C7 C8 O2 -54.6(3) O3 C7 C8 C11 -58.4(3) C5 C7 C8 C11 -176.9(2) C7 O3 C9 O4 -171.1(3) C7 O3 C9 C10 8.4(3) O4 C9 C10 C16 -25.0(4) O3 C9 C10 C16 155.6(3) O4 C9 C10 C11 151.4(3) O3 C9 C10 C11 -28.1(4) C16 C10 C11 C12 -1.3(4) C9 C10 C11 C12 -177.8(2) C16 C10 C11 C8 177.4(2) C9 C10 C11 C8 1.0(4) O2 C8 C11 C12 101.5(3) C7 C8 C11 C12 -139.6(3) O2 C8 C11 C10 -77.2(3) C7 C8 C11 C10 41.7(3) C10 C11 C12 C13 5.5(4) C8 C11 C12 C13 -173.2(3) C11 C12 C13 C14 -3.5(4) C12 C13 C14 C16 -2.8(4) C12 C13 C14 C15 176.3(3) Si1 O5 C16 C14 117.7(2) Si1 O5 C16 C10 -64.0(3) C13 C14 C16 O5 -174.7(2) C15 C14 C16 O5 6.3(4) C13 C14 C16 C10 7.0(4) C15 C14 C16 C10 -172.0(3) C11 C10 C16 O5 176.7(2) C9 C10 C16 O5 -7.0(4) C11 C10 C16 C14 -5.1(4) C9 C10 C16 C14 171.2(3) O5 Si1 C19 C20 -173.2(2) C17 Si1 C19 C20 66.4(3) C18 Si1 C19 C20 -56.9(3) O5 Si1 C19 C22 -52.9(2) C17 Si1 C19 C22 -173.4(2) C18 Si1 C19 C22 63.3(3) O5 Si1 C19 C21 67.8(2) C17 Si1 C19 C21 -52.6(2) C18 Si1 C19 C21 -175.9(2)