#------------------------------------------------------------------------------ #$Date: 2021-03-23 07:38:01 +0200 (Tue, 23 Mar 2021) $ #$Revision: 263233 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/25/7242500.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_7242500 loop_ _publ_author_name Ismiyarto, 'Kishi, Nobuki' 'Adachi, Yuki' 'Jiang, Rui' 'Doi, Takahiro' 'Zhou, Da-Yang' 'Asano, Kaori' 'Obora, Yasushi' 'Suzuki, Takayoshi' 'Sasai, Hiroaki' 'Suzuki, Takeyuki' _publ_section_title ; Catalytic enantioselective intramolecular Tishchenko reaction of meso-dialdehyde: synthesis of (S)-cedarmycins ; _journal_issue 19 _journal_name_full 'RSC Advances' _journal_page_first 11606 _journal_page_last 11609 _journal_paper_doi 10.1039/D1RA00915J _journal_volume 11 _journal_year 2021 _chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk' _chemical_formula_moiety 'C19 H18 O4' _chemical_formula_sum 'C19 H18 O4' _chemical_formula_weight 310.35 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_update_record ; 2020-08-11 deposited with the CCDC. 2021-03-11 downloaded from the CCDC. ; _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 90.0000 _cell_formula_units_Z 4 _cell_length_a 8.91118(16) _cell_length_b 11.0174(2) _cell_length_c 15.8907(11) _cell_measurement_reflns_used 27839 _cell_measurement_temperature 123 _cell_measurement_theta_max 68.23 _cell_measurement_theta_min 4.01 _cell_volume 1560.12(12) _computing_cell_refinement 'RAPID AUTO' _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_data_reduction 'RAPID AUTO' _computing_molecular_graphics 'CrystalStructure 4.2' _computing_publication_material 'CrystalStructure 4.2 (Rigaku, 2017)' _computing_structure_refinement 'SHELXL Version 2017/1 (Sheldrick, 2008)' _computing_structure_solution 'SHELXT Version 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 123 _diffrn_detector_area_resol_mean 10.000 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID 191R' _diffrn_measurement_method \w _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_reflns_av_R_equivalents 0.0327 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 29839 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.687 _diffrn_reflns_theta_max 68.234 _diffrn_reflns_theta_min 4.885 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.754 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_correction_T_min 0.822 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'ABSCOR (Rigaku, 1995)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 656.00 _exptl_crystal_size_max 0.136 _exptl_crystal_size_mid 0.082 _exptl_crystal_size_min 0.077 _refine_diff_density_max 0.15 _refine_diff_density_min -0.22 _refine_ls_abs_structure_details ; Flack x determined using 1068 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.13(6) _refine_ls_extinction_coef 0.0009(2) _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_hydrogen_treatment constr _refine_ls_number_parameters 209 _refine_ls_number_reflns 2849 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0342 _refine_ls_R_factor_gt 0.0319 _refine_ls_shift/su_max 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0290P)^2^+0.3245P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0698 _refine_ls_wR_factor_ref 0.0707 _reflns_Friedel_coverage 0.727 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 2704 _reflns_number_total 2849 _reflns_threshold_expression F^2^>2.0\s(F^2^) _cod_data_source_file d1ra00915j2.cif _cod_data_source_block No2_1_1 _cod_database_code 7242500 _shelx_res_file ; TITL No2_1_1 shelxl.res created by SHELXL-2017/1 at 15:11:40 on 26-Feb-2018 CELL 1.54187 8.91118 11.01742 15.89067 90.00000 90.00000 90.00000 ZERR 4 0.00016 0.00020 0.00112 0.00000 0.00000 0.00000 LATT -1 SYMM .50-X, -Y, .50+Z SYMM .50+X, .50-Y, -Z SYMM -X, .50+Y, .50-Z SFAC C H O UNIT 76 72 16 L.S. 30 FMAP 2 PLAN 5 WPDB -2 HTAB BOND $H CONF LIST 4 TEMP -150.0 ACTA SIZE 0.136 0.082 0.077 WGHT 0.029000 0.324500 EXTI 0.000881 FVAR 0.58382 O1 3 0.841720 0.451947 0.240649 11.00000 0.03277 0.03086 = 0.02769 0.00174 -0.00086 -0.00532 O2 3 0.784003 0.248829 0.212516 11.00000 0.02077 0.03064 = 0.03114 -0.00510 0.00303 0.00017 O3 3 0.853850 0.338359 -0.017245 11.00000 0.04242 0.05337 = 0.03046 -0.00100 0.00073 -0.00348 O4 3 0.817780 0.147972 0.026585 11.00000 0.04840 0.05191 = 0.04041 -0.01098 0.00602 -0.00940 C5 1 0.758828 0.348506 0.267122 11.00000 0.02584 0.02533 = 0.02781 -0.00206 0.00089 -0.00200 C6 1 0.809013 0.320359 0.356500 11.00000 0.01904 0.03291 = 0.02917 0.00038 0.00169 0.00172 C7 1 0.589226 0.370603 0.264036 11.00000 0.02470 0.03198 = 0.02547 -0.00110 -0.00136 0.00265 C8 1 0.888224 0.404072 0.405002 11.00000 0.02589 0.03640 = 0.03267 0.00153 -0.00019 -0.00090 AFIX 43 H8 2 0.916031 0.480088 0.381483 11.00000 -1.20000 AFIX 0 C9 1 0.937237 0.224894 0.191552 11.00000 0.02123 0.03598 = 0.03539 -0.00248 0.00249 0.00305 AFIX 23 H9A 2 0.953219 0.136282 0.186402 11.00000 -1.20000 H9B 2 1.003626 0.255790 0.236679 11.00000 -1.20000 AFIX 0 C10 1 0.926758 0.376760 0.487757 11.00000 0.02981 0.04834 = 0.03352 -0.00099 -0.00716 -0.00066 AFIX 43 H10 2 0.981257 0.433975 0.520413 11.00000 -1.20000 AFIX 0 C11 1 0.528714 0.467356 0.307025 11.00000 0.03159 0.03329 = 0.03722 -0.00761 -0.00727 0.00399 AFIX 43 H11 2 0.593401 0.523140 0.334634 11.00000 -1.20000 AFIX 0 C12 1 0.975458 0.286706 0.108873 11.00000 0.02401 0.04242 = 0.03472 0.00012 0.00717 0.00089 AFIX 13 H12 2 1.080832 0.264063 0.093976 11.00000 -1.20000 AFIX 0 C13 1 0.769346 0.209579 0.392167 11.00000 0.02759 0.03398 = 0.03560 0.00140 -0.00053 -0.00259 AFIX 43 H13 2 0.716033 0.151464 0.359659 11.00000 -1.20000 AFIX 0 C14 1 0.963377 0.425186 0.104366 11.00000 0.03044 0.04284 = 0.03198 0.00320 -0.00079 -0.00553 AFIX 13 H14 2 1.059214 0.463860 0.123151 11.00000 -1.20000 AFIX 0 C15 1 0.830114 0.478079 0.152753 11.00000 0.03816 0.03383 = 0.02801 0.00440 -0.00314 -0.00190 AFIX 23 H15A 2 0.826802 0.567081 0.144382 11.00000 -1.20000 H15B 2 0.735672 0.443331 0.130480 11.00000 -1.20000 AFIX 0 C16 1 0.874732 0.245408 0.037417 11.00000 0.03177 0.04750 = 0.03183 -0.00609 0.00858 0.00095 C17 1 0.375070 0.484584 0.310629 11.00000 0.03368 0.03773 = 0.03493 -0.00605 -0.00485 0.01155 AFIX 43 H17 2 0.335407 0.551157 0.341433 11.00000 -1.20000 AFIX 0 C18 1 0.807041 0.183507 0.474669 11.00000 0.03161 0.04227 = 0.04075 0.01094 0.00249 0.00059 AFIX 43 H18 2 0.778550 0.107962 0.498656 11.00000 -1.20000 AFIX 0 C19 1 0.886029 0.266877 0.522452 11.00000 0.03187 0.05393 = 0.03239 0.00821 -0.00229 0.00551 AFIX 43 H19 2 0.912110 0.248447 0.578993 11.00000 -1.20000 AFIX 0 C20 1 0.280346 0.407119 0.270494 11.00000 0.02584 0.05199 = 0.04726 -0.01165 -0.00543 0.00977 AFIX 43 H20 2 0.174939 0.419755 0.272309 11.00000 -1.20000 AFIX 0 C21 1 0.940664 0.443429 0.010358 11.00000 0.03948 0.04946 = 0.03348 0.00557 0.00327 -0.00534 AFIX 23 H21A 2 0.885160 0.519599 -0.000760 11.00000 -1.20000 H21B 2 1.038380 0.446850 -0.019188 11.00000 -1.20000 AFIX 0 C22 1 0.492266 0.293068 0.224057 11.00000 0.02855 0.07433 = 0.10468 -0.06129 -0.00771 0.00937 AFIX 43 H22 2 0.531134 0.225992 0.193460 11.00000 -1.20000 AFIX 0 C23 1 0.338997 0.310931 0.227559 11.00000 0.02659 0.09603 = 0.12675 -0.07687 -0.01336 0.00923 AFIX 43 H23 2 0.273768 0.255711 0.199806 11.00000 -1.20000 AFIX 0 HKLF 4 REM No2_1_1 REM R1 = 0.0319 for 2704 Fo > 4sig(Fo) and 0.0342 for all 2849 data REM 209 parameters refined using 0 restraints END WGHT 0.0290 0.3244 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.152, deepest hole -0.217, 1-sigma level 0.028 Q1 1 0.5248 0.3583 0.2006 11.00000 0.05 0.15 Q2 1 0.3311 0.2834 0.2398 11.00000 0.05 0.14 Q3 1 0.3557 0.3010 0.2573 11.00000 0.05 0.12 Q4 1 0.3835 0.3590 0.1914 11.00000 0.05 0.12 Q5 1 0.5260 0.2924 0.2637 11.00000 0.05 0.11 ; _shelx_res_checksum 15065 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 +X,+Y,+Z 2 1/2-X,-Y,1/2+Z 3 1/2+X,1/2-Y,-Z 4 -X,1/2+Y,1/2-Z 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.84172(16) 0.45195(13) 0.24065(9) 0.0304(3) Uani 1 1 d . . . . . O2 O 0.78400(14) 0.24883(13) 0.21252(9) 0.0275(3) Uani 1 1 d . . . . . O3 O 0.85385(19) 0.33836(15) -0.01724(10) 0.0421(4) Uani 1 1 d . . . . . O4 O 0.8178(2) 0.14797(16) 0.02659(11) 0.0469(4) Uani 1 1 d . . . . . C5 C 0.7588(2) 0.34851(18) 0.26712(13) 0.0263(4) Uani 1 1 d . . . . . C6 C 0.8090(2) 0.32036(19) 0.35650(13) 0.0270(4) Uani 1 1 d . . . . . C7 C 0.5892(2) 0.37060(19) 0.26404(13) 0.0274(4) Uani 1 1 d . . . . . C8 C 0.8882(2) 0.4041(2) 0.40500(14) 0.0317(5) Uani 1 1 d . . . . . H8 H 0.916031 0.480088 0.381483 0.038 Uiso 1 1 calc R U . . . C9 C 0.9372(2) 0.2249(2) 0.19155(14) 0.0309(5) Uani 1 1 d . . . . . H9A H 0.953219 0.136282 0.186402 0.037 Uiso 1 1 calc R U . . . H9B H 1.003626 0.255790 0.236679 0.037 Uiso 1 1 calc R U . . . C10 C 0.9268(3) 0.3768(2) 0.48776(15) 0.0372(5) Uani 1 1 d . . . . . H10 H 0.981257 0.433975 0.520413 0.045 Uiso 1 1 calc R U . . . C11 C 0.5287(2) 0.4674(2) 0.30703(14) 0.0340(5) Uani 1 1 d . . . . . H11 H 0.593401 0.523140 0.334634 0.041 Uiso 1 1 calc R U . . . C12 C 0.9755(2) 0.2867(2) 0.10887(14) 0.0337(5) Uani 1 1 d . . . . . H12 H 1.080832 0.264063 0.093976 0.040 Uiso 1 1 calc R U . . . C13 C 0.7693(2) 0.2096(2) 0.39217(15) 0.0324(5) Uani 1 1 d . . . . . H13 H 0.716033 0.151464 0.359659 0.039 Uiso 1 1 calc R U . . . C14 C 0.9634(3) 0.4252(2) 0.10437(14) 0.0351(5) Uani 1 1 d . . . . . H14 H 1.059214 0.463860 0.123151 0.042 Uiso 1 1 calc R U . . . C15 C 0.8301(3) 0.4781(2) 0.15275(14) 0.0333(5) Uani 1 1 d . . . . . H15A H 0.826802 0.567081 0.144382 0.040 Uiso 1 1 calc R U . . . H15B H 0.735672 0.443331 0.130480 0.040 Uiso 1 1 calc R U . . . C16 C 0.8747(3) 0.2454(2) 0.03742(14) 0.0370(5) Uani 1 1 d . . . . . C17 C 0.3751(2) 0.4846(2) 0.31063(15) 0.0354(5) Uani 1 1 d . . . . . H17 H 0.335407 0.551157 0.341433 0.043 Uiso 1 1 calc R U . . . C18 C 0.8070(3) 0.1835(2) 0.47467(16) 0.0382(5) Uani 1 1 d . . . . . H18 H 0.778550 0.107962 0.498656 0.046 Uiso 1 1 calc R U . . . C19 C 0.8860(2) 0.2669(2) 0.52245(15) 0.0394(6) Uani 1 1 d . . . . . H19 H 0.912110 0.248447 0.578993 0.047 Uiso 1 1 calc R U . . . C20 C 0.2803(3) 0.4071(2) 0.27049(16) 0.0417(6) Uani 1 1 d . . . . . H20 H 0.174939 0.419755 0.272309 0.050 Uiso 1 1 calc R U . . . C21 C 0.9407(3) 0.4434(2) 0.01036(14) 0.0408(6) Uani 1 1 d . . . . . H21A H 0.885160 0.519599 -0.000760 0.049 Uiso 1 1 calc R U . . . H21B H 1.038380 0.446850 -0.019188 0.049 Uiso 1 1 calc R U . . . C22 C 0.4923(3) 0.2931(3) 0.2241(2) 0.0692(11) Uani 1 1 d . . . . . H22 H 0.531134 0.225992 0.193460 0.083 Uiso 1 1 calc R U . . . C23 C 0.3390(3) 0.3109(3) 0.2276(2) 0.0831(13) Uani 1 1 d . . . . . H23 H 0.273768 0.255711 0.199806 0.100 Uiso 1 1 calc R U . . . 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 O1 0.0328(8) 0.0309(7) 0.0277(8) 0.0017(6) -0.0009(6) -0.0053(6) O2 0.0208(7) 0.0306(7) 0.0311(8) -0.0051(6) 0.0030(5) 0.0002(6) O3 0.0424(9) 0.0534(10) 0.0305(9) -0.0010(8) 0.0007(7) -0.0035(8) O4 0.0484(10) 0.0519(10) 0.0404(10) -0.0110(9) 0.0060(8) -0.0094(9) C5 0.0258(10) 0.0253(9) 0.0278(11) -0.0021(9) 0.0009(8) -0.0020(8) C6 0.0190(10) 0.0329(11) 0.0292(11) 0.0004(9) 0.0017(8) 0.0017(8) C7 0.0247(10) 0.0320(10) 0.0255(11) -0.0011(8) -0.0014(9) 0.0027(8) C8 0.0259(11) 0.0364(11) 0.0327(12) 0.0015(9) -0.0002(9) -0.0009(9) C9 0.0212(10) 0.0360(12) 0.0354(12) -0.0025(10) 0.0025(9) 0.0030(9) C10 0.0298(11) 0.0483(14) 0.0335(13) -0.0010(10) -0.0072(10) -0.0007(10) C11 0.0316(11) 0.0333(12) 0.0372(13) -0.0076(10) -0.0073(10) 0.0040(9) C12 0.0240(10) 0.0424(13) 0.0347(12) 0.0001(10) 0.0072(9) 0.0009(10) C13 0.0276(11) 0.0340(11) 0.0356(13) 0.0014(10) -0.0005(9) -0.0026(9) C14 0.0304(11) 0.0428(13) 0.0320(12) 0.0032(10) -0.0008(10) -0.0055(10) C15 0.0382(12) 0.0338(11) 0.0280(11) 0.0044(9) -0.0031(10) -0.0019(10) C16 0.0318(11) 0.0475(14) 0.0318(13) -0.0061(11) 0.0086(9) 0.0009(11) C17 0.0337(12) 0.0377(12) 0.0349(13) -0.0060(10) -0.0049(10) 0.0115(10) C18 0.0316(12) 0.0423(13) 0.0407(13) 0.0109(11) 0.0025(10) 0.0006(10) C19 0.0319(11) 0.0539(15) 0.0324(12) 0.0082(11) -0.0023(10) 0.0055(11) C20 0.0258(12) 0.0520(14) 0.0473(15) -0.0117(12) -0.0054(10) 0.0098(10) C21 0.0395(13) 0.0495(14) 0.0335(13) 0.0056(11) 0.0033(11) -0.0053(11) C22 0.0286(13) 0.074(2) 0.105(3) -0.061(2) -0.0077(14) 0.0094(13) C23 0.0266(14) 0.096(2) 0.127(3) -0.077(2) -0.0134(17) 0.0092(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (Vol. C, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; 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 C5 O1 C15 114.38(16) . . ? C5 O2 C9 115.89(15) . . ? C16 O3 C21 109.50(17) . . ? O2 C5 O1 110.96(15) . . ? O2 C5 C6 111.54(16) . . ? O1 C5 C6 106.68(16) . . ? O2 C5 C7 105.05(15) . . ? O1 C5 C7 112.07(16) . . ? C6 C5 C7 110.64(16) . . ? C13 C6 C8 118.9(2) . . ? C13 C6 C5 118.98(19) . . ? C8 C6 C5 122.03(19) . . ? C22 C7 C11 117.8(2) . . ? C22 C7 C5 122.52(19) . . ? C11 C7 C5 119.60(18) . . ? C10 C8 C6 120.3(2) . . ? C10 C8 H8 119.9 . . ? C6 C8 H8 119.9 . . ? O2 C9 C12 109.45(17) . . ? O2 C9 H9A 109.8 . . ? C12 C9 H9A 109.8 . . ? O2 C9 H9B 109.8 . . ? C12 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C19 C10 C8 120.2(2) . . ? C19 C10 H10 119.9 . . ? C8 C10 H10 119.9 . . ? C7 C11 C17 121.0(2) . . ? C7 C11 H11 119.5 . . ? C17 C11 H11 119.5 . . ? C16 C12 C9 112.35(18) . . ? C16 C12 C14 102.84(19) . . ? C9 C12 C14 118.14(19) . . ? C16 C12 H12 107.7 . . ? C9 C12 H12 107.7 . . ? C14 C12 H12 107.7 . . ? C18 C13 C6 120.4(2) . . ? C18 C13 H13 119.8 . . ? C6 C13 H13 119.8 . . ? C21 C14 C15 109.88(19) . . ? C21 C14 C12 100.78(19) . . ? C15 C14 C12 114.24(18) . . ? C21 C14 H14 110.5 . . ? C15 C14 H14 110.5 . . ? C12 C14 H14 110.5 . . ? O1 C15 C14 110.98(18) . . ? O1 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? O1 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? O4 C16 O3 121.7(2) . . ? O4 C16 C12 128.7(2) . . ? O3 C16 C12 109.5(2) . . ? C20 C17 C11 120.6(2) . . ? C20 C17 H17 119.7 . . ? C11 C17 H17 119.7 . . ? C13 C18 C19 120.4(2) . . ? C13 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? C10 C19 C18 119.8(2) . . ? C10 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C17 C20 C23 119.0(2) . . ? C17 C20 H20 120.5 . . ? C23 C20 H20 120.5 . . ? O3 C21 C14 105.12(18) . . ? O3 C21 H21A 110.7 . . ? C14 C21 H21A 110.7 . . ? O3 C21 H21B 110.7 . . ? C14 C21 H21B 110.7 . . ? H21A C21 H21B 108.8 . . ? C7 C22 C23 121.0(2) . . ? C7 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C20 C23 C22 120.6(3) . . ? C20 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? 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 O1 C5 1.422(2) . ? O1 C15 1.430(3) . ? O2 C5 1.417(2) . ? O2 C9 1.430(2) . ? O3 C16 1.356(3) . ? O3 C21 1.460(3) . ? O4 C16 1.200(3) . ? C5 C6 1.521(3) . ? C5 C7 1.532(3) . ? C6 C13 1.391(3) . ? C6 C8 1.394(3) . ? C7 C22 1.371(3) . ? C7 C11 1.376(3) . ? C8 C10 1.392(3) . ? C8 H8 0.9500 . ? C9 C12 1.519(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C19 1.379(3) . ? C10 H10 0.9500 . ? C11 C17 1.383(3) . ? C11 H11 0.9500 . ? C12 C16 1.517(3) . ? C12 C14 1.531(3) . ? C12 H12 1.0000 . ? C13 C18 1.384(3) . ? C13 H13 0.9500 . ? C14 C21 1.521(3) . ? C14 C15 1.530(3) . ? C14 H14 1.0000 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C17 C20 1.359(3) . ? C17 H17 0.9500 . ? C18 C19 1.384(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C23 1.364(4) . ? C20 H20 0.9500 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.381(4) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? 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 C9 O2 C5 O1 47.0(2) . . . . ? C9 O2 C5 C6 -71.8(2) . . . . ? C9 O2 C5 C7 168.28(16) . . . . ? C15 O1 C5 O2 47.2(2) . . . . ? C15 O1 C5 C6 168.85(16) . . . . ? C15 O1 C5 C7 -69.9(2) . . . . ? O2 C5 C6 C13 -45.7(2) . . . . ? O1 C5 C6 C13 -167.04(18) . . . . ? C7 C5 C6 C13 70.8(2) . . . . ? O2 C5 C6 C8 136.95(19) . . . . ? O1 C5 C6 C8 15.6(2) . . . . ? C7 C5 C6 C8 -106.5(2) . . . . ? O2 C5 C7 C22 8.0(3) . . . . ? O1 C5 C7 C22 128.6(3) . . . . ? C6 C5 C7 C22 -112.5(3) . . . . ? O2 C5 C7 C11 -176.11(19) . . . . ? O1 C5 C7 C11 -55.5(3) . . . . ? C6 C5 C7 C11 63.4(3) . . . . ? C13 C6 C8 C10 0.0(3) . . . . ? C5 C6 C8 C10 177.3(2) . . . . ? C5 O2 C9 C12 -94.9(2) . . . . ? C6 C8 C10 C19 -0.4(3) . . . . ? C22 C7 C11 C17 0.9(4) . . . . ? C5 C7 C11 C17 -175.2(2) . . . . ? O2 C9 C12 C16 -58.0(2) . . . . ? O2 C9 C12 C14 61.5(2) . . . . ? C8 C6 C13 C18 0.5(3) . . . . ? C5 C6 C13 C18 -176.91(19) . . . . ? C16 C12 C14 C21 -31.6(2) . . . . ? C9 C12 C14 C21 -155.95(19) . . . . ? C16 C12 C14 C15 86.1(2) . . . . ? C9 C12 C14 C15 -38.2(3) . . . . ? C5 O1 C15 C14 -96.7(2) . . . . ? C21 C14 C15 O1 174.48(18) . . . . ? C12 C14 C15 O1 62.1(3) . . . . ? C21 O3 C16 O4 -177.9(2) . . . . ? C21 O3 C16 C12 2.3(2) . . . . ? C9 C12 C16 O4 -32.2(3) . . . . ? C14 C12 C16 O4 -160.3(2) . . . . ? C9 C12 C16 O3 147.51(18) . . . . ? C14 C12 C16 O3 19.4(2) . . . . ? C7 C11 C17 C20 -1.1(4) . . . . ? C6 C13 C18 C19 -0.7(3) . . . . ? C8 C10 C19 C18 0.2(3) . . . . ? C13 C18 C19 C10 0.3(3) . . . . ? C11 C17 C20 C23 1.0(4) . . . . ? C16 O3 C21 C14 -23.5(2) . . . . ? C15 C14 C21 O3 -87.0(2) . . . . ? C12 C14 C21 O3 33.8(2) . . . . ? C11 C7 C22 C23 -0.6(5) . . . . ? C5 C7 C22 C23 175.3(3) . . . . ? C17 C20 C23 C22 -0.7(5) . . . . ? C7 C22 C23 C20 0.5(6) . . . . ?