#------------------------------------------------------------------------------ #$Date: 2024-11-07 03:51:43 +0200 (Thu, 07 Nov 2024) $ #$Revision: 295818 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160218.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_7160218 loop_ _publ_author_name 'Chen, Shushuai' 'Zheng, Chengyu' 'Yang, Guan-Zhou' 'Zhou, Jun-Su' 'He, Shijun' 'Fan, Yao Yue' 'Yue, Jian-Min' _publ_section_title ; Highly oxygenated Steroids with Immunosuppressive activity from Solanum undatum ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01642D _journal_year 2024 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C29 H42 O5' _chemical_formula_sum 'C29 H42 O5' _chemical_formula_weight 470.62 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2022-06-16 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2023-04-12 deposited with the CCDC. 2024-11-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.8880(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.6163(3) _cell_length_b 7.9028(2) _cell_length_c 17.3878(5) _cell_measurement_reflns_used 9932 _cell_measurement_temperature 170 _cell_measurement_theta_max 74.49 _cell_measurement_theta_min 2.62 _cell_volume 1282.77(6) _computing_cell_refinement 'SAINT V8.40A (?, 2016)' _computing_data_reduction 'SAINT V8.40A (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 170.0 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_unetI/netI 0.0360 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 16663 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.966 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 74.487 _diffrn_reflns_theta_min 2.618 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.648 _exptl_absorpt_correction_T_max 0.7538 _exptl_absorpt_correction_T_min 0.5727 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1597 before and 0.0933 after correction. The Ratio of minimum to maximum transmission is 0.7598. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.218 _exptl_crystal_description block _exptl_crystal_F_000 512 _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.269 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.033 _refine_ls_abs_structure_details ; Flack x determined using 2190 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.07(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 314 _refine_ls_number_reflns 5052 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0314 _refine_ls_R_factor_gt 0.0309 _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^)+(0.0459P)^2^+0.1407P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0817 _refine_ls_wR_factor_ref 0.0822 _reflns_Friedel_coverage 0.818 _reflns_Friedel_fraction_full 0.973 _reflns_Friedel_fraction_max 0.941 _reflns_number_gt 4954 _reflns_number_total 5052 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL cu_2022489_0m_a.res in P2(1) cu_2022489_0m.res created by SHELXL-2018/3 at 21:44:38 on 16-Jun-2022 REM Old TITL cu_2022489_0m in P2(1) REM SHELXT solution in P2(1) REM R1 0.099, Rweak 0.032, Alpha 0.005, Orientation as input REM Flack x = 0.096 ( 0.042 ) from Parsons' quotients REM Formula found by SHELXT: C29 O5 CELL 1.54178 9.6163 7.9028 17.3878 90 103.888 90 ZERR 2 0.0003 0.0002 0.0005 0 0.001 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H O UNIT 58 84 10 L.S. 20 PLAN 20 SIZE 0.15 0.08 0.05 TEMP -103.15 BOND $H list 4 fmap 2 ACTA REM REM REM WGHT 0.045900 0.140700 FVAR 1.36994 O2 3 0.509616 0.509403 0.645560 11.00000 0.01994 0.03110 = 0.02892 0.00455 0.00591 -0.00260 AFIX 147 H2 2 0.556606 0.427807 0.669743 11.00000 -1.50000 AFIX 0 O3 3 0.341009 0.608744 0.856752 11.00000 0.03273 0.02566 = 0.02365 0.00184 0.00928 0.00501 O4 3 0.576711 0.337958 0.926385 11.00000 0.03167 0.02448 = 0.03174 -0.00119 0.00854 0.00255 O5 3 0.287133 0.374981 0.926375 11.00000 0.02837 0.03028 = 0.03760 0.00440 0.00793 -0.00219 O1 3 0.312885 0.736728 0.276332 11.00000 0.06516 0.05970 = 0.03637 -0.00056 0.01237 -0.03633 C6 1 0.157819 0.207368 0.309914 11.00000 0.03464 0.02535 = 0.03292 -0.00972 0.01304 -0.00517 AFIX 43 H6 2 0.141303 0.101837 0.283107 11.00000 -1.20000 AFIX 0 C8 1 0.198321 0.371652 0.436025 11.00000 0.01924 0.02111 = 0.02606 -0.00233 0.00786 -0.00032 AFIX 13 H8 2 0.094590 0.380102 0.436086 11.00000 -1.20000 AFIX 0 C14 1 0.287074 0.378101 0.521417 11.00000 0.01933 0.01839 = 0.02659 -0.00087 0.00769 0.00010 AFIX 13 H14 2 0.389753 0.375240 0.518708 11.00000 -1.20000 AFIX 0 C26 1 0.367527 0.525514 0.930017 11.00000 0.03042 0.02314 = 0.02508 0.00228 0.00861 0.00271 AFIX 13 H26 2 0.336867 0.602981 0.968337 11.00000 -1.20000 AFIX 0 C16 1 0.323602 0.309110 0.660852 11.00000 0.02616 0.02219 = 0.02755 0.00228 0.00834 -0.00118 AFIX 23 H16A 2 0.408961 0.245946 0.690000 11.00000 -1.20000 H16B 2 0.248659 0.301349 0.691034 11.00000 -1.20000 AFIX 0 C18 1 0.111945 0.564674 0.572335 11.00000 0.02410 0.03726 = 0.02704 -0.00296 0.00617 0.00817 AFIX 137 H18A 2 0.048470 0.562865 0.519025 11.00000 -1.50000 H18B 2 0.102408 0.673450 0.597642 11.00000 -1.50000 H18C 2 0.085567 0.472805 0.603941 11.00000 -1.50000 AFIX 0 C12 1 0.316027 0.687880 0.521708 11.00000 0.04025 0.01932 = 0.02277 -0.00065 0.00400 -0.00272 AFIX 23 H12A 2 0.419442 0.676436 0.523944 11.00000 -1.20000 H12B 2 0.301593 0.796083 0.547418 11.00000 -1.20000 AFIX 0 C23 1 0.574134 0.574757 0.832969 11.00000 0.03001 0.02981 = 0.02549 0.00020 0.00821 -0.00230 AFIX 23 H23A 2 0.629386 0.522311 0.797952 11.00000 -1.20000 H23B 2 0.589342 0.698639 0.832775 11.00000 -1.20000 AFIX 0 C15 1 0.268030 0.233820 0.577015 11.00000 0.03627 0.02161 = 0.02943 0.00004 0.00998 -0.00514 AFIX 23 H15A 2 0.324856 0.133462 0.569379 11.00000 -1.20000 H15B 2 0.166042 0.200862 0.567859 11.00000 -1.20000 AFIX 0 C7 1 0.223313 0.205349 0.397006 11.00000 0.02680 0.02088 = 0.03252 -0.00282 0.01046 0.00010 AFIX 23 H7A 2 0.327586 0.184875 0.406248 11.00000 -1.20000 H7B 2 0.181463 0.111353 0.421647 11.00000 -1.20000 AFIX 0 C22 1 0.415655 0.535949 0.801575 11.00000 0.02785 0.02322 = 0.02325 -0.00051 0.00767 0.00123 AFIX 13 H22 2 0.401876 0.410470 0.800360 11.00000 -1.20000 AFIX 0 C9 1 0.238373 0.523659 0.389902 11.00000 0.02044 0.02294 = 0.02335 -0.00055 0.00600 0.00051 AFIX 13 H9 2 0.340867 0.507960 0.388385 11.00000 -1.20000 AFIX 0 C5 1 0.121218 0.347263 0.267585 11.00000 0.02709 0.03059 = 0.02780 -0.00717 0.00861 -0.00490 C1 1 0.230351 0.623765 0.250026 11.00000 0.02864 0.03004 = 0.02943 0.00147 0.00759 -0.00186 C11 1 0.230371 0.690643 0.434209 11.00000 0.03735 0.02024 = 0.02470 0.00179 0.00549 0.00080 AFIX 23 H11A 2 0.128756 0.715657 0.432392 11.00000 -1.20000 H11B 2 0.267308 0.783355 0.406357 11.00000 -1.20000 AFIX 0 C17 1 0.362908 0.497159 0.651010 11.00000 0.02045 0.02246 = 0.02453 0.00197 0.00740 0.00002 C19 1 0.003336 0.617264 0.291924 11.00000 0.02653 0.04321 = 0.02885 -0.00076 0.00387 0.00868 AFIX 137 H19A 2 -0.049814 0.566772 0.327714 11.00000 -1.50000 H19B 2 -0.052444 0.605758 0.237060 11.00000 -1.50000 H19C 2 0.020217 0.737425 0.304739 11.00000 -1.50000 AFIX 0 C25 1 0.523799 0.479016 0.965206 11.00000 0.03034 0.02057 = 0.02591 0.00100 0.00563 -0.00010 C20 1 0.341102 0.609192 0.720185 11.00000 0.03054 0.02517 = 0.02271 -0.00006 0.00538 0.00357 AFIX 13 H20 2 0.236111 0.606365 0.717588 11.00000 -1.20000 AFIX 0 C29 1 0.137529 0.404413 0.901276 11.00000 0.02981 0.04857 = 0.04518 0.00919 0.00721 -0.00144 AFIX 137 H29A 2 0.113811 0.443559 0.846187 11.00000 -1.50000 H29B 2 0.109612 0.490871 0.935091 11.00000 -1.50000 H29C 2 0.085826 0.299138 0.905214 11.00000 -1.50000 AFIX 0 C27 1 0.562884 0.474908 1.054402 11.00000 0.04070 0.02899 = 0.02615 0.00432 0.00545 0.00270 AFIX 137 H27A 2 0.489720 0.411946 1.073234 11.00000 -1.50000 H27B 2 0.568402 0.590827 1.074935 11.00000 -1.50000 H27C 2 0.655964 0.419276 1.073083 11.00000 -1.50000 AFIX 0 C24 1 0.627368 0.507541 0.916338 11.00000 0.02797 0.02613 = 0.02811 -0.00043 0.00533 -0.00044 C21 1 0.378920 0.795519 0.712668 11.00000 0.06466 0.02328 = 0.02737 -0.00100 0.00497 0.00290 AFIX 137 H21A 2 0.381447 0.853935 0.762701 11.00000 -1.50000 H21B 2 0.306507 0.848211 0.670016 11.00000 -1.50000 H21C 2 0.473033 0.803769 0.700473 11.00000 -1.50000 AFIX 0 C10 1 0.149123 0.525144 0.301837 11.00000 0.02260 0.02627 = 0.02356 -0.00162 0.00657 -0.00013 C28 1 0.783851 0.537101 0.953414 11.00000 0.02990 0.04743 = 0.03686 0.00274 0.00287 -0.00424 AFIX 137 H28A 2 0.809763 0.482393 1.005483 11.00000 -1.50000 H28B 2 0.802086 0.658945 0.959575 11.00000 -1.50000 H28C 2 0.841513 0.489196 0.919305 11.00000 -1.50000 AFIX 0 C13 1 0.268199 0.540936 0.566669 11.00000 0.02153 0.02090 = 0.02350 -0.00092 0.00592 0.00091 C2 1 0.201764 0.583601 0.164886 11.00000 0.05043 0.03890 = 0.02903 0.00274 0.01559 0.00234 AFIX 43 H2A 2 0.244985 0.651278 0.131887 11.00000 -1.20000 AFIX 0 C4 1 0.052000 0.336875 0.179857 11.00000 0.04796 0.04147 = 0.02946 -0.00949 0.00391 -0.00805 AFIX 23 H4A 2 0.061337 0.220025 0.161194 11.00000 -1.20000 H4B 2 -0.051397 0.362604 0.170971 11.00000 -1.20000 AFIX 0 C3 1 0.118065 0.456668 0.132792 11.00000 0.05992 0.03902 = 0.02670 -0.00379 0.01071 0.00223 AFIX 43 H3 2 0.099183 0.441163 0.077063 11.00000 -1.20000 AFIX 0 HKLF 4 REM cu_2022489_0m_a.res in P2(1) REM wR2 = 0.0822, GooF = S = 1.053, Restrained GooF = 1.053 for all data REM R1 = 0.0309 for 4954 Fo > 4sig(Fo) and 0.0314 for all 5052 data REM 314 parameters refined using 1 restraints END WGHT 0.0452 0.1469 REM Highest difference peak 0.269, deepest hole -0.147, 1-sigma level 0.033 Q1 1 0.2188 0.4483 0.4121 11.00000 0.05 0.27 Q2 1 0.2794 0.4615 0.5411 11.00000 0.05 0.26 Q3 1 0.3511 0.5537 0.6889 11.00000 0.05 0.24 Q4 1 0.1375 0.4347 0.2836 11.00000 0.05 0.22 Q5 1 0.2302 0.6077 0.4130 11.00000 0.05 0.22 Q6 1 0.2838 0.6161 0.5444 11.00000 0.05 0.21 Q7 1 0.2252 0.2883 0.4151 11.00000 0.05 0.21 Q8 1 0.3390 0.4097 0.6599 11.00000 0.05 0.20 Q9 1 0.1919 0.5227 0.3493 11.00000 0.05 0.19 Q10 1 0.2757 0.3021 0.5479 11.00000 0.05 0.18 Q11 1 0.3155 0.5243 0.6104 11.00000 0.05 0.18 Q12 1 0.2441 0.3751 0.4803 11.00000 0.05 0.18 Q13 1 0.1969 0.5578 0.2762 11.00000 0.05 0.17 Q14 1 0.1028 0.2786 0.2934 11.00000 0.05 0.17 Q15 1 0.3824 0.5741 0.7587 11.00000 0.05 0.17 Q16 1 0.1013 0.3841 0.1569 11.00000 0.05 0.17 Q17 1 0.2088 0.4704 0.1528 11.00000 0.05 0.17 Q18 1 0.3621 0.7021 0.7137 11.00000 0.05 0.16 Q19 1 0.0863 0.3455 0.2225 11.00000 0.05 0.16 Q20 1 0.5749 0.5483 0.9462 11.00000 0.05 0.16 REM The information below was added by Olex2. REM REM R1 = 0.0309 for 4954 Fo > 4sig(Fo) and 0.0314 for all 16680 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.27, deepest hole -0.15 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0314 REM R1_gt = 0.0309 REM wR_ref = 0.0822 REM GOOF = 1.053 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 16680 REM Reflections_gt = 4954 REM Parameters = n/a REM Hole = -0.15 REM Peak = 0.27 REM Flack = 0.07(5) ; _cod_data_source_file d4ob01642d2.cif _cod_data_source_block cu_2022489_0m _cod_database_code 7160218 _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. ; _shelx_estimated_absorpt_t_max 0.968 _shelx_estimated_absorpt_t_min 0.909 _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, All O(H) groups 2.a Ternary CH refined with riding coordinates: C8(H8), C14(H14), C26(H26), C22(H22), C9(H9), C20(H20) 2.b Secondary CH2 refined with riding coordinates: C16(H16A,H16B), C12(H12A,H12B), C23(H23A,H23B), C15(H15A,H15B), C7(H7A,H7B), C11(H11A,H11B), C4(H4A,H4B) 2.c Aromatic/amide H refined with riding coordinates: C6(H6), C2(H2A), C3(H3) 2.d Idealised Me refined as rotating group: C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C29(H29A,H29B,H29C), C27(H27A,H27B, H27C), C21(H21A,H21B,H21C), C28(H28A,H28B,H28C) 2.e Idealised tetrahedral OH refined as rotating group: O2(H2) ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, 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 O2 O 0.50962(11) 0.50940(17) 0.64556(7) 0.0266(3) Uani 1 1 d . . . . . H2 H 0.556606 0.427807 0.669743 0.040 Uiso 1 1 calc GR . . . . O3 O 0.34101(13) 0.60874(16) 0.85675(7) 0.0269(3) Uani 1 1 d . . . . . O4 O 0.57671(13) 0.33796(15) 0.92639(7) 0.0291(3) Uani 1 1 d . . . . . O5 O 0.28713(13) 0.37498(18) 0.92638(8) 0.0321(3) Uani 1 1 d . . . . . O1 O 0.31289(19) 0.7367(2) 0.27633(9) 0.0537(5) Uani 1 1 d . . . . . C6 C 0.15782(19) 0.2074(2) 0.30991(11) 0.0301(4) Uani 1 1 d . . . . . H6 H 0.141303 0.101837 0.283107 0.036 Uiso 1 1 calc R . . . . C8 C 0.19832(15) 0.3717(2) 0.43602(9) 0.0217(3) Uani 1 1 d . . . . . H8 H 0.094590 0.380102 0.436086 0.026 Uiso 1 1 calc R . . . . C14 C 0.28707(15) 0.3781(2) 0.52142(9) 0.0211(3) Uani 1 1 d . . . . . H14 H 0.389753 0.375240 0.518708 0.025 Uiso 1 1 calc R . . . . C26 C 0.36753(18) 0.5255(2) 0.93002(10) 0.0259(3) Uani 1 1 d . . . . . H26 H 0.336867 0.602981 0.968337 0.031 Uiso 1 1 calc R . . . . C16 C 0.32360(17) 0.3091(2) 0.66085(10) 0.0250(3) Uani 1 1 d . . . . . H16A H 0.408961 0.245946 0.690000 0.030 Uiso 1 1 calc R . . . . H16B H 0.248659 0.301349 0.691034 0.030 Uiso 1 1 calc R . . . . C18 C 0.11195(17) 0.5647(2) 0.57233(10) 0.0295(4) Uani 1 1 d . . . . . H18A H 0.048470 0.562865 0.519025 0.044 Uiso 1 1 calc GR . . . . H18B H 0.102408 0.673450 0.597642 0.044 Uiso 1 1 calc GR . . . . H18C H 0.085567 0.472805 0.603941 0.044 Uiso 1 1 calc GR . . . . C12 C 0.3160(2) 0.6879(2) 0.52171(10) 0.0281(4) Uani 1 1 d . . . . . H12A H 0.419442 0.676436 0.523944 0.034 Uiso 1 1 calc R . . . . H12B H 0.301593 0.796083 0.547418 0.034 Uiso 1 1 calc R . . . . C23 C 0.57413(18) 0.5748(2) 0.83297(10) 0.0282(4) Uani 1 1 d . . . . . H23A H 0.629386 0.522311 0.797952 0.034 Uiso 1 1 calc R . . . . H23B H 0.589342 0.698639 0.832775 0.034 Uiso 1 1 calc R . . . . C15 C 0.2680(2) 0.2338(2) 0.57701(10) 0.0287(4) Uani 1 1 d . . . . . H15A H 0.324856 0.133462 0.569379 0.034 Uiso 1 1 calc R . . . . H15B H 0.166042 0.200862 0.567859 0.034 Uiso 1 1 calc R . . . . C7 C 0.22331(18) 0.2053(2) 0.39701(10) 0.0262(3) Uani 1 1 d . . . . . H7A H 0.327586 0.184875 0.406248 0.031 Uiso 1 1 calc R . . . . H7B H 0.181463 0.111353 0.421647 0.031 Uiso 1 1 calc R . . . . C22 C 0.41565(17) 0.5359(2) 0.80157(9) 0.0245(3) Uani 1 1 d . . . . . H22 H 0.401876 0.410470 0.800360 0.029 Uiso 1 1 calc R . . . . C9 C 0.23837(16) 0.5237(2) 0.38990(9) 0.0221(3) Uani 1 1 d . . . . . H9 H 0.340867 0.507960 0.388385 0.027 Uiso 1 1 calc R . . . . C5 C 0.12122(18) 0.3473(2) 0.26759(10) 0.0281(4) Uani 1 1 d . . . . . C1 C 0.23035(18) 0.6238(2) 0.25003(10) 0.0293(4) Uani 1 1 d . . . . . C11 C 0.2304(2) 0.6906(2) 0.43421(10) 0.0278(3) Uani 1 1 d . . . . . H11A H 0.128756 0.715657 0.432392 0.033 Uiso 1 1 calc R . . . . H11B H 0.267308 0.783355 0.406357 0.033 Uiso 1 1 calc R . . . . C17 C 0.36291(16) 0.4972(2) 0.65101(9) 0.0221(3) Uani 1 1 d . . . . . C19 C 0.00334(18) 0.6173(3) 0.29192(11) 0.0333(4) Uani 1 1 d . . . . . H19A H -0.049814 0.566772 0.327714 0.050 Uiso 1 1 calc GR . . . . H19B H -0.052444 0.605758 0.237060 0.050 Uiso 1 1 calc GR . . . . H19C H 0.020217 0.737425 0.304739 0.050 Uiso 1 1 calc GR . . . . C25 C 0.52380(18) 0.4790(2) 0.96521(10) 0.0258(3) Uani 1 1 d . . . . . C20 C 0.34110(18) 0.6092(2) 0.72018(10) 0.0263(3) Uani 1 1 d . . . . . H20 H 0.236111 0.606365 0.717588 0.032 Uiso 1 1 calc R . . . . C29 C 0.1375(2) 0.4044(3) 0.90128(13) 0.0415(5) Uani 1 1 d . . . . . H29A H 0.113811 0.443559 0.846187 0.062 Uiso 1 1 calc GR . . . . H29B H 0.109612 0.490871 0.935091 0.062 Uiso 1 1 calc GR . . . . H29C H 0.085826 0.299138 0.905214 0.062 Uiso 1 1 calc GR . . . . C27 C 0.5629(2) 0.4749(2) 1.05440(11) 0.0324(4) Uani 1 1 d . . . . . H27A H 0.489720 0.411946 1.073234 0.049 Uiso 1 1 calc GR . . . . H27B H 0.568402 0.590827 1.074935 0.049 Uiso 1 1 calc GR . . . . H27C H 0.655964 0.419276 1.073083 0.049 Uiso 1 1 calc GR . . . . C24 C 0.62737(17) 0.5075(2) 0.91634(10) 0.0276(3) Uani 1 1 d . . . . . C21 C 0.3789(3) 0.7955(3) 0.71267(11) 0.0395(4) Uani 1 1 d . . . . . H21A H 0.381447 0.853935 0.762701 0.059 Uiso 1 1 calc GR . . . . H21B H 0.306507 0.848211 0.670016 0.059 Uiso 1 1 calc GR . . . . H21C H 0.473033 0.803769 0.700473 0.059 Uiso 1 1 calc GR . . . . C10 C 0.14912(16) 0.5251(2) 0.30184(9) 0.0240(3) Uani 1 1 d . . . . . C28 C 0.78385(19) 0.5371(3) 0.95341(12) 0.0389(4) Uani 1 1 d . . . . . H28A H 0.809763 0.482393 1.005483 0.058 Uiso 1 1 calc GR . . . . H28B H 0.802086 0.658945 0.959575 0.058 Uiso 1 1 calc GR . . . . H28C H 0.841513 0.489196 0.919305 0.058 Uiso 1 1 calc GR . . . . C13 C 0.26820(16) 0.5409(2) 0.56667(9) 0.0219(3) Uani 1 1 d . . . . . C2 C 0.2018(2) 0.5836(3) 0.16489(11) 0.0384(4) Uani 1 1 d . . . . . H2A H 0.244985 0.651278 0.131887 0.046 Uiso 1 1 calc R . . . . C4 C 0.0520(2) 0.3369(3) 0.17986(11) 0.0405(5) Uani 1 1 d . . . . . H4A H 0.061337 0.220025 0.161194 0.049 Uiso 1 1 calc R . . . . H4B H -0.051397 0.362604 0.170971 0.049 Uiso 1 1 calc R . . . . C3 C 0.1181(3) 0.4567(3) 0.13279(12) 0.0418(5) Uani 1 1 d . . . . . H3 H 0.099183 0.441163 0.077063 0.050 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 O2 0.0199(5) 0.0311(6) 0.0289(6) 0.0046(5) 0.0059(4) -0.0026(5) O3 0.0327(6) 0.0257(6) 0.0236(6) 0.0018(5) 0.0093(4) 0.0050(5) O4 0.0317(6) 0.0245(7) 0.0317(6) -0.0012(5) 0.0085(5) 0.0025(5) O5 0.0284(6) 0.0303(6) 0.0376(7) 0.0044(5) 0.0079(5) -0.0022(5) O1 0.0652(10) 0.0597(11) 0.0364(8) -0.0006(7) 0.0124(7) -0.0363(9) C6 0.0346(9) 0.0253(9) 0.0329(9) -0.0097(7) 0.0130(7) -0.0052(7) C8 0.0192(6) 0.0211(8) 0.0261(8) -0.0023(6) 0.0079(5) -0.0003(6) C14 0.0193(6) 0.0184(7) 0.0266(8) -0.0009(6) 0.0077(5) 0.0001(6) C26 0.0304(8) 0.0231(8) 0.0251(7) 0.0023(6) 0.0086(6) 0.0027(7) C16 0.0262(7) 0.0222(8) 0.0275(8) 0.0023(6) 0.0083(6) -0.0012(6) C18 0.0241(8) 0.0373(10) 0.0270(8) -0.0030(7) 0.0062(6) 0.0082(7) C12 0.0403(9) 0.0193(8) 0.0228(8) -0.0006(6) 0.0040(7) -0.0027(7) C23 0.0300(8) 0.0298(9) 0.0255(8) 0.0002(6) 0.0082(6) -0.0023(7) C15 0.0363(9) 0.0216(8) 0.0294(9) 0.0000(7) 0.0100(7) -0.0051(7) C7 0.0268(8) 0.0209(8) 0.0325(9) -0.0028(7) 0.0105(6) 0.0001(6) C22 0.0279(8) 0.0232(8) 0.0232(7) -0.0005(6) 0.0077(6) 0.0012(6) C9 0.0204(7) 0.0229(8) 0.0234(7) -0.0005(6) 0.0060(6) 0.0005(6) C5 0.0271(7) 0.0306(9) 0.0278(8) -0.0072(7) 0.0086(6) -0.0049(7) C1 0.0286(8) 0.0300(9) 0.0294(9) 0.0015(7) 0.0076(6) -0.0019(7) C11 0.0373(9) 0.0202(8) 0.0247(8) 0.0018(6) 0.0055(7) 0.0008(7) C17 0.0204(7) 0.0225(8) 0.0245(8) 0.0020(6) 0.0074(5) 0.0000(6) C19 0.0265(8) 0.0432(10) 0.0288(9) -0.0008(8) 0.0039(6) 0.0087(8) C25 0.0303(8) 0.0206(8) 0.0259(8) 0.0010(6) 0.0056(6) -0.0001(6) C20 0.0305(8) 0.0252(8) 0.0227(8) -0.0001(6) 0.0054(6) 0.0036(7) C29 0.0298(9) 0.0486(13) 0.0452(11) 0.0092(9) 0.0072(8) -0.0014(8) C27 0.0407(9) 0.0290(9) 0.0262(9) 0.0043(7) 0.0054(7) 0.0027(7) C24 0.0280(8) 0.0261(9) 0.0281(8) -0.0004(7) 0.0053(6) -0.0004(7) C21 0.0647(13) 0.0233(9) 0.0274(9) -0.0010(7) 0.0050(8) 0.0029(9) C10 0.0226(7) 0.0263(8) 0.0236(7) -0.0016(6) 0.0066(6) -0.0001(6) C28 0.0299(9) 0.0474(12) 0.0369(9) 0.0027(9) 0.0029(7) -0.0042(8) C13 0.0215(7) 0.0209(8) 0.0235(7) -0.0009(6) 0.0059(6) 0.0009(6) C2 0.0504(11) 0.0389(11) 0.0290(9) 0.0027(8) 0.0156(8) 0.0023(9) C4 0.0480(11) 0.0415(12) 0.0295(9) -0.0095(8) 0.0039(8) -0.0080(9) C3 0.0599(12) 0.0390(11) 0.0267(9) -0.0038(8) 0.0107(9) 0.0022(10) 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 C17 O2 H2 109.5 . . ? C26 O3 C22 113.87(12) . . ? C24 O4 C25 60.90(11) . . ? C26 O5 C29 112.31(15) . . ? C7 C6 H6 117.9 . . ? C5 C6 H6 117.9 . . ? C5 C6 C7 124.18(16) . . ? C14 C8 H8 108.8 . . ? C14 C8 C9 109.18(13) . . ? C7 C8 H8 108.8 . . ? C7 C8 C14 110.54(13) . . ? C7 C8 C9 110.74(12) . . ? C9 C8 H8 108.8 . . ? C8 C14 H14 106.3 . . ? C8 C14 C15 117.71(13) . . ? C8 C14 C13 114.69(13) . . ? C15 C14 H14 106.3 . . ? C15 C14 C13 104.61(12) . . ? C13 C14 H14 106.3 . . ? O3 C26 O5 112.11(14) . . ? O3 C26 H26 107.5 . . ? O3 C26 C25 115.12(14) . . ? O5 C26 H26 107.5 . . ? O5 C26 C25 106.93(13) . . ? C25 C26 H26 107.5 . . ? H16A C16 H16B 108.5 . . ? C15 C16 H16A 110.2 . . ? C15 C16 H16B 110.2 . . ? C15 C16 C17 107.61(13) . . ? C17 C16 H16A 110.2 . . ? C17 C16 H16B 110.2 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C13 C18 H18A 109.5 . . ? C13 C18 H18B 109.5 . . ? C13 C18 H18C 109.5 . . ? H12A C12 H12B 108.0 . . ? C11 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12A 109.4 . . ? C13 C12 H12B 109.4 . . ? C13 C12 C11 111.02(14) . . ? H23A C23 H23B 108.1 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? C24 C23 H23A 109.5 . . ? C24 C23 H23B 109.5 . . ? C24 C23 C22 110.63(14) . . ? C14 C15 C16 103.98(13) . . ? C14 C15 H15A 111.0 . . ? C14 C15 H15B 111.0 . . ? C16 C15 H15A 111.0 . . ? C16 C15 H15B 111.0 . . ? H15A C15 H15B 109.0 . . ? C6 C7 C8 111.64(14) . . ? C6 C7 H7A 109.3 . . ? C6 C7 H7B 109.3 . . ? C8 C7 H7A 109.3 . . ? C8 C7 H7B 109.3 . . ? H7A C7 H7B 108.0 . . ? O3 C22 C23 107.17(13) . . ? O3 C22 H22 108.9 . . ? O3 C22 C20 105.33(13) . . ? C23 C22 H22 108.9 . . ? C23 C22 C20 117.38(14) . . ? C20 C22 H22 108.9 . . ? C8 C9 H9 106.7 . . ? C8 C9 C10 111.56(13) . . ? C11 C9 C8 111.01(12) . . ? C11 C9 H9 106.7 . . ? C11 C9 C10 113.68(13) . . ? C10 C9 H9 106.7 . . ? C6 C5 C10 123.54(15) . . ? C6 C5 C4 120.50(17) . . ? C4 C5 C10 115.93(16) . . ? O1 C1 C10 122.14(16) . . ? O1 C1 C2 119.09(17) . . ? C2 C1 C10 118.72(16) . . ? C12 C11 H11A 108.8 . . ? C12 C11 H11B 108.8 . . ? C9 C11 C12 113.67(14) . . ? C9 C11 H11A 108.8 . . ? C9 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? O2 C17 C16 109.87(13) . . ? O2 C17 C20 109.29(13) . . ? O2 C17 C13 106.38(12) . . ? C16 C17 C13 102.25(13) . . ? C20 C17 C16 112.32(13) . . ? C20 C17 C13 116.36(13) . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? O4 C25 C26 114.74(14) . . ? O4 C25 C27 115.60(14) . . ? O4 C25 C24 59.35(11) . . ? C27 C25 C26 113.37(14) . . ? C24 C25 C26 117.97(14) . . ? C24 C25 C27 124.13(15) . . ? C22 C20 C17 112.31(14) . . ? C22 C20 H20 106.0 . . ? C17 C20 H20 106.0 . . ? C21 C20 C22 111.90(15) . . ? C21 C20 C17 113.88(15) . . ? C21 C20 H20 106.0 . . ? O5 C29 H29A 109.5 . . ? O5 C29 H29B 109.5 . . ? O5 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27B 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O4 C24 C23 113.17(14) . . ? O4 C24 C25 59.75(10) . . ? O4 C24 C28 114.93(15) . . ? C25 C24 C23 119.09(14) . . ? C25 C24 C28 121.40(15) . . ? C28 C24 C23 115.41(15) . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C5 C10 C9 112.26(14) . . ? C5 C10 C1 107.74(13) . . ? C5 C10 C19 108.63(14) . . ? C1 C10 C9 109.90(13) . . ? C1 C10 C19 105.63(15) . . ? C19 C10 C9 112.37(13) . . ? C24 C28 H28A 109.5 . . ? C24 C28 H28B 109.5 . . ? C24 C28 H28C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C14 C13 C17 100.37(12) . . ? C18 C13 C14 111.74(13) . . ? C18 C13 C17 108.88(13) . . ? C12 C13 C14 106.61(12) . . ? C12 C13 C18 110.94(14) . . ? C12 C13 C17 117.82(13) . . ? C1 C2 H2A 118.8 . . ? C3 C2 C1 122.34(18) . . ? C3 C2 H2A 118.8 . . ? C5 C4 H4A 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C3 C4 C5 112.14(16) . . ? C3 C4 H4A 109.2 . . ? C3 C4 H4B 109.2 . . ? C2 C3 C4 123.14(18) . . ? C2 C3 H3 118.4 . . ? C4 C3 H3 118.4 . . ? 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 O2 H2 0.8400 . ? O2 C17 1.4397(18) . ? O3 C26 1.402(2) . ? O3 C22 1.4482(19) . ? O4 C25 1.457(2) . ? O4 C24 1.451(2) . ? O5 C26 1.412(2) . ? O5 C29 1.419(2) . ? O1 C1 1.209(2) . ? C6 H6 0.9500 . ? C6 C7 1.494(2) . ? C6 C5 1.328(3) . ? C8 H8 1.0000 . ? C8 C14 1.526(2) . ? C8 C7 1.524(2) . ? C8 C9 1.544(2) . ? C14 H14 1.0000 . ? C14 C15 1.534(2) . ? C14 C13 1.542(2) . ? C26 H26 1.0000 . ? C26 C25 1.525(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C16 C15 1.546(2) . ? C16 C17 1.553(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C18 C13 1.541(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C12 C11 1.547(2) . ? C12 C13 1.531(2) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C23 C22 1.522(2) . ? C23 C24 1.513(2) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C22 H22 1.0000 . ? C22 C20 1.538(2) . ? C9 H9 1.0000 . ? C9 C11 1.539(2) . ? C9 C10 1.565(2) . ? C5 C10 1.525(2) . ? C5 C4 1.513(2) . ? C1 C10 1.538(2) . ? C1 C2 1.474(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C17 C20 1.548(2) . ? C17 C13 1.568(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C19 C10 1.552(2) . ? C25 C27 1.506(2) . ? C25 C24 1.473(2) . ? C20 H20 1.0000 . ? C20 C21 1.530(3) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C24 C28 1.506(2) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C2 H2A 0.9500 . ? C2 C3 1.323(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C3 1.490(3) . ? C3 H3 0.9500 . ?