#------------------------------------------------------------------------------ #$Date: 2023-11-06 04:33:02 +0200 (Mon, 06 Nov 2023) $ #$Revision: 287286 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247676.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_7247676 loop_ _publ_author_name 'Zhang, Xiao' 'Zhou, Qian' 'Zhou, Yue' 'Wang, Zihao' 'Wang, Jun' 'Wang, Mingfu' _publ_section_title ; Asymmetric synthesis of chiral (thio)chromanes and exploration on their structure-activity relationship in macrophages. ; _journal_issue 43 _journal_name_full 'RSC advances' _journal_page_first 30391 _journal_page_last 30400 _journal_paper_doi 10.1039/d3ra06428j _journal_volume 13 _journal_year 2023 _chemical_absolute_configuration ad _chemical_formula_moiety 'C20 H22 O3' _chemical_formula_sum 'C20 H22 O3' _chemical_formula_weight 310.37 _chemical_name_common cxy1822 _chemical_name_systematic 3ao _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 dual _audit_creation_date 2021-11-09 _audit_creation_method ; Olex2 1.5 (compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6405) ; _audit_update_record ; 2023-09-20 deposited with the CCDC. 2023-10-06 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.4702(3) _cell_length_b 9.9613(4) _cell_length_c 25.6312(11) _cell_measurement_reflns_used 9835 _cell_measurement_temperature 100 _cell_measurement_theta_max 68.61 _cell_measurement_theta_min 3.45 _cell_volume 1651.97(12) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)' _computing_data_reduction 'SAINT V8.38A (Bruker, 2018)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 100 _diffrn_detector 'Bruker PHOTON 100 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CMOS area detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker CMOS area detector' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_unetI/netI 0.0217 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 19161 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.603 _diffrn_reflns_theta_min 3.449 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_type 'Incoatec I\ms' _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.660 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.7069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0648 before and 0.0556 after correction. The Ratio of minimum to maximum transmission is 0.9387. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.248 _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.33 _refine_diff_density_max 0.158 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.030 _refine_ls_abs_structure_details ; Flack x determined using 1213 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.12(6) _refine_ls_extinction_coef 0.0086(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 3041 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0252 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0343P)^2^+0.2813P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0639 _refine_ls_wR_factor_ref 0.0645 _reflns_Friedel_coverage 0.705 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.998 _reflns_number_gt 2959 _reflns_number_total 3041 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06428j2.cif _cod_data_source_block cxy1822 _cod_database_code 7247676 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C8(H8) 2.b Secondary CH2 refined with riding coordinates: C7(H7A,H7B), C14(H14A,H14B), C15(H15A,H15B) 2.c Aromatic/amide H refined with riding coordinates: C4(H4), C11(H11), C12(H12), C16(H16), C17(H17), C19(H19), C20(H20) 2.d X=CH2 refined with riding coordinates: C18(H18A,H18B) 2.e Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C13(H13A,H13B,H13C) ; _shelx_res_file ; TITL cxy1822_a.res in P2(1)2(1)2(1) cxy1822.res created by SHELXL-2018/3 at 10:46:47 on 09-Nov-2021 CELL 1.54178 6.4702 9.9613 25.6312 90 90 90 ZERR 4 0.0003 0.0004 0.0011 0 0 0 LATT -1 SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5-X,-Y,0.5+Z SFAC C H O UNIT 80 88 12 L.S. 4 PLAN 1 0 0 TEMP -173.18 CONF HTAB BOND $H fmap 2 acta MORE -1 REM REM REM WGHT 0.034300 0.281300 EXTI 0.008566 FVAR 0.97217 O1 3 -0.773589 -0.509583 -0.471479 11.00000 0.02784 0.02996 = 0.01667 0.00154 -0.00378 -0.00859 O2 3 -0.453713 -0.359684 -0.455501 11.00000 0.02642 0.02517 = 0.01623 0.00385 0.00085 -0.00832 O3 3 -0.821275 -0.328782 -0.098145 11.00000 0.02634 0.02042 = 0.01894 -0.00298 0.00376 -0.00543 C1 1 -0.947693 -0.593641 -0.482148 11.00000 0.03082 0.03992 = 0.02182 -0.00283 -0.00503 -0.01269 AFIX 137 H1A 2 -1.067252 -0.561965 -0.462161 11.00000 -1.50000 H1B 2 -0.915499 -0.686227 -0.472093 11.00000 -1.50000 H1C 2 -0.979646 -0.590337 -0.519500 11.00000 -1.50000 AFIX 0 C2 1 -0.707747 -0.503308 -0.420920 11.00000 0.01997 0.01863 = 0.01648 -0.00058 -0.00166 0.00171 C3 1 -0.531437 -0.422228 -0.412263 11.00000 0.02002 0.01569 = 0.01668 0.00267 0.00312 0.00125 C4 1 -0.453000 -0.408302 -0.362565 11.00000 0.01671 0.01441 = 0.02045 0.00042 0.00056 0.00031 AFIX 43 H4 2 -0.334013 -0.354124 -0.357252 11.00000 -1.20000 AFIX 0 C5 1 -0.545187 -0.472577 -0.319403 11.00000 0.01613 0.01353 = 0.01745 0.00070 0.00075 0.00344 C6 1 -0.456531 -0.454913 -0.266145 11.00000 0.01787 0.01305 = 0.01800 0.00185 0.00052 0.00371 C7 1 -0.576108 -0.508054 -0.219869 11.00000 0.01780 0.01569 = 0.01582 0.00143 -0.00040 0.00130 AFIX 23 H7A 2 -0.483717 -0.510265 -0.189092 11.00000 -1.20000 H7B 2 -0.619751 -0.601374 -0.227294 11.00000 -1.20000 AFIX 0 C8 1 -0.769804 -0.423212 -0.206479 11.00000 0.01709 0.01610 = 0.01624 0.00211 0.00002 0.00086 AFIX 13 H8 2 -0.854550 -0.414078 -0.238912 11.00000 -1.20000 AFIX 0 C9 1 -0.900795 -0.492841 -0.165678 11.00000 0.01457 0.01616 = 0.01741 0.00311 -0.00015 0.00238 C10 1 -0.921522 -0.442166 -0.115107 11.00000 0.01754 0.01533 = 0.02004 0.00088 -0.00056 0.00058 C11 1 -1.051480 -0.504171 -0.078846 11.00000 0.02293 0.02428 = 0.01828 0.00252 0.00249 0.00123 AFIX 43 H11 2 -1.065021 -0.468181 -0.044693 11.00000 -1.20000 AFIX 0 C12 1 -1.160269 -0.618034 -0.092825 11.00000 0.02122 0.02556 = 0.02515 0.00837 0.00434 -0.00262 AFIX 43 H12 2 -1.249368 -0.659908 -0.068268 11.00000 -1.20000 AFIX 0 C13 1 -0.284122 -0.269335 -0.447211 11.00000 0.03060 0.02920 = 0.02015 0.00318 0.00262 -0.01258 AFIX 137 H13A 2 -0.163844 -0.319851 -0.434778 11.00000 -1.50000 H13B 2 -0.323076 -0.202059 -0.421104 11.00000 -1.50000 H13C 2 -0.249628 -0.224392 -0.480089 11.00000 -1.50000 AFIX 0 C14 1 -0.714190 -0.281931 -0.187525 11.00000 0.02458 0.01581 = 0.02279 0.00196 0.00507 0.00022 AFIX 23 H14A 2 -0.598495 -0.246138 -0.208630 11.00000 -1.20000 H14B 2 -0.834457 -0.221630 -0.192104 11.00000 -1.20000 AFIX 0 C15 1 -0.652299 -0.285298 -0.130460 11.00000 0.02369 0.01908 = 0.02499 -0.00379 0.00399 -0.00529 AFIX 23 H15A 2 -0.533962 -0.347191 -0.125886 11.00000 -1.20000 H15B 2 -0.607684 -0.194566 -0.119431 11.00000 -1.20000 AFIX 0 C16 1 -1.012147 -0.608793 -0.178300 11.00000 0.01930 0.01922 = 0.01914 0.00017 -0.00124 0.00070 AFIX 43 H16 2 -0.999453 -0.645361 -0.212381 11.00000 -1.20000 AFIX 0 C17 1 -1.139893 -0.671690 -0.142751 11.00000 0.02062 0.02078 = 0.02742 0.00410 -0.00234 -0.00425 AFIX 43 H17 2 -1.213088 -0.750684 -0.152231 11.00000 -1.20000 AFIX 0 C18 1 -0.277096 -0.392872 -0.257935 11.00000 0.01828 0.02566 = 0.01881 0.00399 -0.00167 -0.00006 AFIX 93 H18A 2 -0.200862 -0.358033 -0.286572 11.00000 -1.20000 H18B 2 -0.225350 -0.383462 -0.223442 11.00000 -1.20000 AFIX 0 C19 1 -0.718488 -0.551106 -0.328749 11.00000 0.01861 0.01775 = 0.01756 0.00257 0.00236 0.00046 AFIX 43 H19 2 -0.783856 -0.595220 -0.300332 11.00000 -1.20000 AFIX 0 C20 1 -0.799294 -0.566866 -0.379072 11.00000 0.01935 0.01786 = 0.02220 -0.00035 -0.00005 -0.00227 AFIX 43 H20 2 -0.917687 -0.621578 -0.384403 11.00000 -1.20000 AFIX 0 HKLF 4 REM cxy1822_a.res in P2(1)2(1)2(1) REM wR2 = 0.0645, GooF = S = 1.034, Restrained GooF = 1.034 for all data REM R1 = 0.0252 for 2959 Fo > 4sig(Fo) and 0.0261 for all 3041 data REM 211 parameters refined using 0 restraints END WGHT 0.0342 0.2822 REM Instructions for potential hydrogen bonds EQIV $1 x+1/2, -y-1/2, -z-1 HTAB C13 O1_$1 REM Highest difference peak 0.158, deepest hole -0.136, 1-sigma level 0.030 Q1 1 -0.8294 -0.4654 -0.1816 11.00000 0.05 0.16 ; _shelx_res_checksum 91374 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, 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_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 -0.77359(18) -0.50958(12) -0.47148(4) 0.0248(3) Uani 1 1 d . . . . . O2 O -0.45371(18) -0.35968(11) -0.45550(4) 0.0226(3) Uani 1 1 d . . . . . O3 O -0.82128(18) -0.32878(11) -0.09815(4) 0.0219(3) Uani 1 1 d . . . . . C1 C -0.9477(3) -0.59364(19) -0.48215(7) 0.0309(4) Uani 1 1 d . . . . . H1A H -1.067252 -0.561965 -0.462161 0.046 Uiso 1 1 calc R U . . . H1B H -0.915499 -0.686227 -0.472093 0.046 Uiso 1 1 calc R U . . . H1C H -0.979646 -0.590337 -0.519500 0.046 Uiso 1 1 calc R U . . . C2 C -0.7077(2) -0.50331(16) -0.42092(5) 0.0184(3) Uani 1 1 d . . . . . C3 C -0.5314(2) -0.42223(15) -0.41226(6) 0.0175(3) Uani 1 1 d . . . . . C4 C -0.4530(2) -0.40830(14) -0.36257(6) 0.0172(3) Uani 1 1 d . . . . . H4 H -0.334013 -0.354124 -0.357252 0.021 Uiso 1 1 calc R U . . . C5 C -0.5452(2) -0.47258(14) -0.31940(5) 0.0157(3) Uani 1 1 d . . . . . C6 C -0.4565(2) -0.45491(14) -0.26615(5) 0.0163(3) Uani 1 1 d . . . . . C7 C -0.5761(2) -0.50805(15) -0.21987(5) 0.0164(3) Uani 1 1 d . . . . . H7A H -0.483717 -0.510265 -0.189092 0.020 Uiso 1 1 calc R U . . . H7B H -0.619751 -0.601374 -0.227294 0.020 Uiso 1 1 calc R U . . . C8 C -0.7698(2) -0.42321(14) -0.20648(6) 0.0165(3) Uani 1 1 d . . . . . H8 H -0.854550 -0.414078 -0.238912 0.020 Uiso 1 1 calc R U . . . C9 C -0.9008(2) -0.49284(15) -0.16568(6) 0.0160(3) Uani 1 1 d . . . . . C10 C -0.9215(2) -0.44217(15) -0.11511(6) 0.0176(3) Uani 1 1 d . . . . . C11 C -1.0515(3) -0.50417(17) -0.07885(6) 0.0218(3) Uani 1 1 d . . . . . H11 H -1.065021 -0.468181 -0.044693 0.026 Uiso 1 1 calc R U . . . C12 C -1.1603(3) -0.61803(17) -0.09283(6) 0.0240(3) Uani 1 1 d . . . . . H12 H -1.249368 -0.659908 -0.068268 0.029 Uiso 1 1 calc R U . . . C13 C -0.2841(3) -0.26934(17) -0.44721(6) 0.0267(4) Uani 1 1 d . . . . . H13A H -0.163844 -0.319851 -0.434778 0.040 Uiso 1 1 calc R U . . . H13B H -0.323076 -0.202059 -0.421104 0.040 Uiso 1 1 calc R U . . . H13C H -0.249628 -0.224392 -0.480089 0.040 Uiso 1 1 calc R U . . . C14 C -0.7142(3) -0.28193(15) -0.18753(6) 0.0211(3) Uani 1 1 d . . . . . H14A H -0.598495 -0.246138 -0.208630 0.025 Uiso 1 1 calc R U . . . H14B H -0.834457 -0.221630 -0.192104 0.025 Uiso 1 1 calc R U . . . C15 C -0.6523(3) -0.28530(16) -0.13046(6) 0.0226(3) Uani 1 1 d . . . . . H15A H -0.533962 -0.347191 -0.125886 0.027 Uiso 1 1 calc R U . . . H15B H -0.607684 -0.194566 -0.119431 0.027 Uiso 1 1 calc R U . . . C16 C -1.0121(2) -0.60879(15) -0.17830(6) 0.0192(3) Uani 1 1 d . . . . . H16 H -0.999453 -0.645361 -0.212381 0.023 Uiso 1 1 calc R U . . . C17 C -1.1399(3) -0.67169(17) -0.14275(6) 0.0229(3) Uani 1 1 d . . . . . H17 H -1.213088 -0.750684 -0.152231 0.028 Uiso 1 1 calc R U . . . C18 C -0.2771(3) -0.39287(16) -0.25794(6) 0.0209(3) Uani 1 1 d . . . . . H18A H -0.200862 -0.358033 -0.286572 0.025 Uiso 1 1 calc R U . . . H18B H -0.225350 -0.383462 -0.223442 0.025 Uiso 1 1 calc R U . . . C19 C -0.7185(2) -0.55111(14) -0.32875(6) 0.0180(3) Uani 1 1 d . . . . . H19 H -0.783856 -0.595220 -0.300332 0.022 Uiso 1 1 calc R U . . . C20 C -0.7993(3) -0.56687(15) -0.37907(6) 0.0198(3) Uani 1 1 d . . . . . H20 H -0.917687 -0.621578 -0.384403 0.024 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 0.0278(6) 0.0300(6) 0.0167(5) 0.0015(4) -0.0038(4) -0.0086(5) O2 0.0264(6) 0.0252(6) 0.0162(5) 0.0039(4) 0.0008(4) -0.0083(5) O3 0.0263(6) 0.0204(5) 0.0189(5) -0.0030(4) 0.0038(4) -0.0054(5) C1 0.0308(9) 0.0399(10) 0.0218(8) -0.0028(7) -0.0050(7) -0.0127(8) C2 0.0200(7) 0.0186(7) 0.0165(7) -0.0006(5) -0.0017(6) 0.0017(6) C3 0.0200(7) 0.0157(7) 0.0167(7) 0.0027(5) 0.0031(6) 0.0012(6) C4 0.0167(7) 0.0144(7) 0.0204(7) 0.0004(6) 0.0006(6) 0.0003(6) C5 0.0161(7) 0.0135(6) 0.0175(7) 0.0007(5) 0.0008(5) 0.0034(6) C6 0.0179(7) 0.0130(7) 0.0180(7) 0.0018(5) 0.0005(6) 0.0037(6) C7 0.0178(7) 0.0157(7) 0.0158(7) 0.0014(5) -0.0004(5) 0.0013(6) C8 0.0171(7) 0.0161(7) 0.0162(7) 0.0021(5) 0.0000(6) 0.0009(6) C9 0.0146(7) 0.0162(7) 0.0174(7) 0.0031(6) -0.0001(5) 0.0024(6) C10 0.0175(7) 0.0153(7) 0.0200(7) 0.0009(6) -0.0006(6) 0.0006(6) C11 0.0229(7) 0.0243(8) 0.0183(7) 0.0025(6) 0.0025(6) 0.0012(7) C12 0.0212(8) 0.0256(8) 0.0252(8) 0.0084(6) 0.0043(7) -0.0026(7) C13 0.0306(9) 0.0292(8) 0.0201(8) 0.0032(6) 0.0026(7) -0.0126(7) C14 0.0246(8) 0.0158(7) 0.0228(8) 0.0020(6) 0.0051(6) 0.0002(6) C15 0.0237(8) 0.0191(8) 0.0250(8) -0.0038(6) 0.0040(6) -0.0053(7) C16 0.0193(7) 0.0192(7) 0.0191(7) 0.0002(6) -0.0012(6) 0.0007(6) C17 0.0206(7) 0.0208(8) 0.0274(8) 0.0041(6) -0.0023(6) -0.0042(6) C18 0.0183(7) 0.0257(8) 0.0188(7) 0.0040(6) -0.0017(6) -0.0001(6) C19 0.0186(7) 0.0178(7) 0.0176(7) 0.0026(5) 0.0024(6) 0.0005(6) C20 0.0194(7) 0.0179(7) 0.0222(7) -0.0004(6) -0.0001(6) -0.0023(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables 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 C2 O1 C1 117.00(12) . . ? C3 O2 C13 116.55(12) . . ? C10 O3 C15 115.12(12) . . ? O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 115.24(13) . . ? O1 C2 C20 125.66(14) . . ? C20 C2 C3 119.09(13) . . ? O2 C3 C2 115.43(13) . . ? O2 C3 C4 124.60(14) . . ? C4 C3 C2 119.95(13) . . ? C3 C4 H4 119.2 . . ? C3 C4 C5 121.57(14) . . ? C5 C4 H4 119.2 . . ? C4 C5 C6 120.12(13) . . ? C19 C5 C4 117.52(13) . . ? C19 C5 C6 122.36(13) . . ? C5 C6 C7 118.69(13) . . ? C18 C6 C5 122.32(14) . . ? C18 C6 C7 118.98(13) . . ? C6 C7 H7A 108.9 . . ? C6 C7 H7B 108.9 . . ? C6 C7 C8 113.36(12) . . ? H7A C7 H7B 107.7 . . ? C8 C7 H7A 108.9 . . ? C8 C7 H7B 108.9 . . ? C7 C8 H8 108.0 . . ? C9 C8 C7 110.84(11) . . ? C9 C8 H8 108.0 . . ? C9 C8 C14 109.47(12) . . ? C14 C8 C7 112.41(13) . . ? C14 C8 H8 108.0 . . ? C10 C9 C8 121.93(13) . . ? C10 C9 C16 117.60(13) . . ? C16 C9 C8 120.44(13) . . ? O3 C10 C9 123.06(13) . . ? O3 C10 C11 115.93(13) . . ? C11 C10 C9 121.00(14) . . ? C10 C11 H11 120.1 . . ? C12 C11 C10 119.79(14) . . ? C12 C11 H11 120.1 . . ? C11 C12 H12 119.8 . . ? C11 C12 C17 120.32(14) . . ? C17 C12 H12 119.8 . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C8 C14 H14A 109.6 . . ? C8 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C15 C14 C8 110.34(12) . . ? C15 C14 H14A 109.6 . . ? C15 C14 H14B 109.6 . . ? O3 C15 C14 111.18(13) . . ? O3 C15 H15A 109.4 . . ? O3 C15 H15B 109.4 . . ? C14 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C9 C16 H16 119.0 . . ? C17 C16 C9 122.03(14) . . ? C17 C16 H16 119.0 . . ? C12 C17 H17 120.4 . . ? C16 C17 C12 119.26(15) . . ? C16 C17 H17 120.4 . . ? C6 C18 H18A 120.0 . . ? C6 C18 H18B 120.0 . . ? H18A C18 H18B 120.0 . . ? C5 C19 H19 119.2 . . ? C5 C19 C20 121.58(14) . . ? C20 C19 H19 119.2 . . ? C2 C20 C19 120.29(14) . . ? C2 C20 H20 119.9 . . ? C19 C20 H20 119.9 . . ? 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 C1 1.430(2) . ? O1 C2 1.3655(17) . ? O2 C3 1.3672(18) . ? O2 C13 1.435(2) . ? O3 C10 1.3731(19) . ? O3 C15 1.4384(19) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.415(2) . ? C2 C20 1.379(2) . ? C3 C4 1.378(2) . ? C4 H4 0.9500 . ? C4 C5 1.411(2) . ? C5 C6 1.491(2) . ? C5 C19 1.388(2) . ? C6 C7 1.5118(19) . ? C6 C18 1.332(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.550(2) . ? C8 H8 1.0000 . ? C8 C9 1.514(2) . ? C8 C14 1.532(2) . ? C9 C10 1.397(2) . ? C9 C16 1.399(2) . ? C10 C11 1.397(2) . ? C11 H11 0.9500 . ? C11 C12 1.382(2) . ? C12 H12 0.9500 . ? C12 C17 1.393(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.517(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16 0.9500 . ? C16 C17 1.381(2) . ? C17 H17 0.9500 . ? C18 H18A 0.9500 . ? C18 H18B 0.9500 . ? C19 H19 0.9500 . ? C19 C20 1.401(2) . ? C20 H20 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 O1 C2 C3 O2 1.1(2) . . . . ? O1 C2 C3 C4 179.58(13) . . . . ? O1 C2 C20 C19 -179.12(15) . . . . ? O2 C3 C4 C5 177.93(13) . . . . ? O3 C10 C11 C12 179.27(14) . . . . ? C1 O1 C2 C3 178.20(14) . . . . ? C1 O1 C2 C20 -2.6(2) . . . . ? C2 C3 C4 C5 -0.4(2) . . . . ? C3 C2 C20 C19 0.0(2) . . . . ? C3 C4 C5 C6 -179.81(13) . . . . ? C3 C4 C5 C19 0.1(2) . . . . ? C4 C5 C6 C7 171.15(13) . . . . ? C4 C5 C6 C18 -8.1(2) . . . . ? C4 C5 C19 C20 0.2(2) . . . . ? C5 C6 C7 C8 -73.08(17) . . . . ? C5 C19 C20 C2 -0.3(2) . . . . ? C6 C5 C19 C20 -179.81(14) . . . . ? C6 C7 C8 C9 171.07(12) . . . . ? C6 C7 C8 C14 -66.07(16) . . . . ? C7 C8 C9 C10 111.58(15) . . . . ? C7 C8 C9 C16 -70.79(17) . . . . ? C7 C8 C14 C15 -80.40(16) . . . . ? C8 C9 C10 O3 -1.9(2) . . . . ? C8 C9 C10 C11 176.70(14) . . . . ? C8 C9 C16 C17 -177.23(14) . . . . ? C8 C14 C15 O3 -62.91(17) . . . . ? C9 C8 C14 C15 43.23(17) . . . . ? C9 C10 C11 C12 0.6(2) . . . . ? C9 C16 C17 C12 0.4(2) . . . . ? C10 O3 C15 C14 47.98(18) . . . . ? C10 C9 C16 C17 0.5(2) . . . . ? C10 C11 C12 C17 0.4(2) . . . . ? C11 C12 C17 C16 -0.9(2) . . . . ? C13 O2 C3 C2 175.68(14) . . . . ? C13 O2 C3 C4 -2.8(2) . . . . ? C14 C8 C9 C10 -12.97(19) . . . . ? C14 C8 C9 C16 164.66(13) . . . . ? C15 O3 C10 C9 -15.9(2) . . . . ? C15 O3 C10 C11 165.39(14) . . . . ? C16 C9 C10 O3 -179.62(14) . . . . ? C16 C9 C10 C11 -1.0(2) . . . . ? C18 C6 C7 C8 106.24(16) . . . . ? C19 C5 C6 C7 -8.8(2) . . . . ? C19 C5 C6 C18 171.91(14) . . . . ? C20 C2 C3 O2 -178.16(13) . . . . ? C20 C2 C3 C4 0.3(2) . . . . ?