#------------------------------------------------------------------------------ #$Date: 2020-05-05 06:55:19 +0300 (Tue, 05 May 2020) $ #$Revision: 251532 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157492.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_7157492 loop_ _publ_author_name 'Yang, Xiao-Chao' 'Xu, Meng' 'Wang, Jin-Bao' 'Liu, Meng-Meng' 'Mathey, Francois' 'Hua, Yuan-Zhao' 'Wang, Mincan' _publ_section_title ; Enantioselective Synthesis of Indanone Spiro-Isochromanone Derivatives via Dinuclear Zinc-Catalyzed Michael/Transesterification Tandem Reaction ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00541J _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C25 H17 Cl O4' _chemical_formula_sum 'C25 H17 Cl O4' _chemical_formula_weight 416.83 _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_Hall 'C 2y' _space_group_name_H-M_alt 'C 1 2 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2019-01-17 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-06-10 deposited with the CCDC. 2020-05-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 96.832(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 17.9619(4) _cell_length_b 9.8922(2) _cell_length_c 22.6104(5) _cell_measurement_reflns_used 8045 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.9200 _cell_measurement_theta_min 4.9400 _cell_volume 3988.95(15) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 42.00 68.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 0.0000 0.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 2 omega -99.00 -55.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 178.0000 -60.0000 44 #__ type_ start__ end____ width___ exp.time_ 3 omega -31.00 2.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -77.0000 120.0000 33 #__ type_ start__ end____ width___ exp.time_ 4 omega -3.00 41.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 -90.0000 44 #__ type_ start__ end____ width___ exp.time_ 5 omega 25.00 63.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -77.0000 120.0000 38 #__ type_ start__ end____ width___ exp.time_ 6 omega 58.00 109.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -150.0000 51 #__ type_ start__ end____ width___ exp.time_ 7 omega 43.00 84.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 37.0000 -60.0000 41 #__ type_ start__ end____ width___ exp.time_ 8 omega 72.00 104.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 90.0000 32 #__ type_ start__ end____ width___ exp.time_ 9 omega 59.00 103.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 120.0000 44 #__ type_ start__ end____ width___ exp.time_ 10 omega -34.00 10.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -19.0000 -90.0000 44 #__ type_ start__ end____ width___ exp.time_ 11 omega 57.00 93.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 60.0000 36 #__ type_ start__ end____ width___ exp.time_ 12 omega 43.00 85.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 37.0000 60.0000 42 #__ type_ start__ end____ width___ exp.time_ 13 omega -3.00 77.00 1.0000 3.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 -120.0000 80 #__ type_ start__ end____ width___ exp.time_ 14 omega 145.00 178.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 15.0000 150.0000 33 #__ type_ start__ end____ width___ exp.time_ 15 omega 66.00 125.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 15.0000 150.0000 59 #__ type_ start__ end____ width___ exp.time_ 16 omega 87.00 133.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -77.0000 90.0000 46 #__ type_ start__ end____ width___ exp.time_ 17 omega 45.00 80.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -77.0000 90.0000 35 #__ type_ start__ end____ width___ exp.time_ 18 omega 50.00 91.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -150.0000 41 #__ type_ start__ end____ width___ exp.time_ 19 omega 48.00 74.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 20 omega 44.00 97.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -45.0000 -90.0000 53 #__ type_ start__ end____ width___ exp.time_ 21 omega 52.00 119.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -61.0000 -30.0000 67 #__ type_ start__ end____ width___ exp.time_ 22 omega 100.00 147.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 150.0000 47 #__ type_ start__ end____ width___ exp.time_ 23 omega 48.00 75.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 120.0000 27 #__ type_ start__ end____ width___ exp.time_ 24 omega 37.00 62.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 25 omega 88.00 177.00 1.0000 9.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 30.0000 89 #__ type_ start__ end____ width___ exp.time_ 26 omega -82.00 -56.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 178.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 27 omega -64.00 -34.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 -57.0000 -150.0000 30 #__ type_ start__ end____ width___ exp.time_ 28 omega 72.00 102.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 -30.0000 30 #__ type_ start__ end____ width___ exp.time_ 29 omega 77.00 103.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 30.0000 26 #__ type_ start__ end____ width___ exp.time_ 30 omega 30.00 56.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 77.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 31 omega 0.00 26.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -57.0000 0.0000 26 #__ type_ start__ end____ width___ exp.time_ 32 omega 18.00 50.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 -30.0000 32 #__ type_ start__ end____ width___ exp.time_ 33 omega 16.00 62.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 37.0000 -120.0000 46 #__ type_ start__ end____ width___ exp.time_ 34 omega 11.00 37.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 76.0000 87.0000 26 #__ type_ start__ end____ width___ exp.time_ 35 omega 21.00 55.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -37.0000 60.0000 34 #__ type_ start__ end____ width___ exp.time_ 36 omega 7.00 103.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 19.0000 -90.0000 96 #__ type_ start__ end____ width___ exp.time_ 37 omega 43.00 94.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 76.0000 87.0000 51 #__ type_ start__ end____ width___ exp.time_ 38 omega 83.00 109.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 60.0000 26 #__ type_ start__ end____ width___ exp.time_ 39 omega -8.00 18.00 1.0000 2.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 107.0000 174.0795 26 #__ type_ start__ end____ width___ exp.time_ 40 omega 56.00 82.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 41 omega 79.00 106.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -180.0000 27 #__ type_ start__ end____ width___ exp.time_ 42 omega 82.00 108.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 30.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 43 omega 72.00 105.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -112.0000 74.0000 33 #__ type_ start__ end____ width___ exp.time_ 44 omega 52.00 99.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -30.0000 47 #__ type_ start__ end____ width___ exp.time_ 45 omega 90.00 116.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 46 omega 114.00 149.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 111.0000 90.0000 35 #__ type_ start__ end____ width___ exp.time_ 47 omega 42.00 68.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 -120.0000 26 #__ type_ start__ end____ width___ exp.time_ 48 omega 64.00 99.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 15.0000 -150.0000 35 #__ type_ start__ end____ width___ exp.time_ 49 omega 118.00 175.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 61.0000 -150.0000 57 #__ type_ start__ end____ width___ exp.time_ 50 omega 79.00 104.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -180.0000 25 #__ type_ start__ end____ width___ exp.time_ 51 omega 138.00 164.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -180.0000 26 #__ type_ start__ end____ width___ exp.time_ 52 omega 84.00 129.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 30.0000 -120.0000 45 #__ type_ start__ end____ width___ exp.time_ 53 omega 54.00 112.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 -60.0000 58 #__ type_ start__ end____ width___ exp.time_ 54 omega 80.00 132.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -120.0000 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0394166000 _diffrn_orient_matrix_UB_12 -0.1186777000 _diffrn_orient_matrix_UB_13 -0.0350594000 _diffrn_orient_matrix_UB_21 -0.0287807000 _diffrn_orient_matrix_UB_22 -0.0517832000 _diffrn_orient_matrix_UB_23 0.0573675000 _diffrn_orient_matrix_UB_31 -0.0712595000 _diffrn_orient_matrix_UB_32 0.0866098000 _diffrn_orient_matrix_UB_33 -0.0137012000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0290 _diffrn_reflns_av_unetI/netI 0.0310 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 17206 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.075 _diffrn_reflns_theta_max 67.075 _diffrn_reflns_theta_min 4.960 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.948 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.26821 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.388 _exptl_crystal_description prism _exptl_crystal_F_000 1728 _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.238 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.041 _refine_ls_abs_structure_details ; Flack x determined using 2793 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack -0.007(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 541 _refine_ls_number_reflns 7132 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.035 _refine_ls_R_factor_all 0.0423 _refine_ls_R_factor_gt 0.0392 _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^)+(0.0652P)^2^+0.6251P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1060 _refine_ls_wR_factor_ref 0.1099 _reflns_Friedel_coverage 0.880 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.999 _reflns_number_gt 6622 _reflns_number_total 7132 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 20190118.res created by SHELXL-2014/7 TITL CF solution in C2 CELL 1.54184 17.961947 9.892241 22.610379 90 96.832 90 ZERR 8 0.000374 0.000202 0.000484 0 0.002 0 LATT -7 SYMM -X,+Y,-Z SFAC C H Cl O UNIT 200 136 8 32 L.S. 4 0 0 PLAN 20 SIZE 0.1 0.13 0.17 MPLA C4 C5 C6 C7 C8 C9 MPLA C11 C12 C13 C14 C15 C16 MPLA C20 C21 C22 C23 C24 C25 MPLA C4' C5' C6' C7' C8' C9' MPLA C11' C12' C13' C14' C15' C16' MPLA C20' C21' C22' C23' C24' C25' BOND$h conf fmap 2 acta REM REM REM WGHT 0.065200 0.625100 FVAR 1.62082 C1 1 0.435857 0.775109 0.423717 11.00000 0.03358 0.04368 = 0.04881 0.00227 0.00755 0.00379 C2 1 0.362492 0.838756 0.440097 11.00000 0.03447 0.03581 = 0.04502 0.00299 0.00895 0.00346 C3 1 0.382017 0.988990 0.452419 11.00000 0.03471 0.04138 = 0.05004 -0.00558 0.00476 0.00245 AFIX 23 H3A 2 0.342238 1.047476 0.434475 11.00000 -1.20000 H3B 2 0.390386 1.006789 0.494878 11.00000 -1.20000 AFIX 0 C4 1 0.452998 1.009694 0.423945 11.00000 0.03634 0.04783 = 0.04334 -0.00270 -0.00006 0.00013 C5 1 0.483989 0.887633 0.409286 11.00000 0.03537 0.04807 = 0.04582 -0.00054 0.00382 0.00093 C6 1 0.550482 0.882019 0.383116 11.00000 0.03904 0.06079 = 0.06547 -0.00952 0.01289 -0.00389 AFIX 43 H6 2 0.571517 0.799705 0.374167 11.00000 -1.20000 AFIX 0 C7 1 0.583631 1.001763 0.371091 11.00000 0.04762 0.08116 = 0.07778 -0.00834 0.02348 -0.01832 AFIX 43 H7 2 0.627380 1.000895 0.352845 11.00000 -1.20000 AFIX 0 C8 1 0.552987 1.125224 0.385706 11.00000 0.05982 0.06020 = 0.08029 -0.00130 0.01586 -0.02487 AFIX 43 H8 2 0.576675 1.205335 0.377257 11.00000 -1.20000 AFIX 0 C9 1 0.487594 1.129860 0.412696 11.00000 0.05432 0.04465 = 0.06594 -0.00473 0.00502 -0.01094 AFIX 43 H9 2 0.467559 1.212088 0.422962 11.00000 -1.20000 AFIX 0 C10 1 0.278288 0.787279 0.512651 11.00000 0.04741 0.03954 = 0.04814 0.00233 0.01522 0.00233 C11 1 0.219425 0.855811 0.472286 11.00000 0.03586 0.03633 = 0.05495 -0.00637 0.01065 -0.00038 C12 1 0.154478 0.901071 0.494364 11.00000 0.04449 0.05111 = 0.06849 -0.01419 0.01906 0.00183 AFIX 43 H12 2 0.148448 0.887786 0.534235 11.00000 -1.20000 AFIX 0 C13 1 0.099436 0.965272 0.457180 11.00000 0.03797 0.05353 = 0.09725 -0.01784 0.01452 0.00534 AFIX 43 H13 2 0.056338 0.996005 0.471959 11.00000 -1.20000 AFIX 0 C14 1 0.108100 0.984010 0.398223 11.00000 0.04168 0.04451 = 0.09358 -0.00571 -0.00567 0.00777 AFIX 43 H14 2 0.070561 1.027099 0.373236 11.00000 -1.20000 AFIX 0 C15 1 0.171790 0.939712 0.375613 11.00000 0.04279 0.04692 = 0.06206 -0.00052 -0.00347 0.00190 AFIX 43 H15 2 0.176984 0.952890 0.335585 11.00000 -1.20000 AFIX 0 C16 1 0.228146 0.875461 0.412586 11.00000 0.03351 0.03330 = 0.05147 -0.00298 0.00433 0.00000 C17 1 0.298154 0.823379 0.389263 11.00000 0.03719 0.03488 = 0.04315 0.00211 0.01025 -0.00006 AFIX 13 H17 2 0.308863 0.880739 0.355960 11.00000 -1.20000 AFIX 0 C18 1 0.286434 0.677475 0.366548 11.00000 0.04647 0.03833 = 0.05097 -0.00295 0.01493 -0.00422 AFIX 23 H18C 2 0.295137 0.616409 0.400226 11.00000 -1.20000 H18D 2 0.234577 0.667001 0.349548 11.00000 -1.20000 AFIX 0 C19 1 0.336637 0.635970 0.320275 11.00000 0.05434 0.04412 = 0.04511 -0.00129 0.01660 -0.00337 C20 1 0.344508 0.487890 0.308250 11.00000 0.05347 0.04076 = 0.03899 -0.00197 0.01365 -0.00472 C21 1 0.400068 0.446181 0.274518 11.00000 0.07867 0.04575 = 0.07327 -0.00356 0.04196 -0.00535 AFIX 43 H21 2 0.430612 0.510582 0.259585 11.00000 -1.20000 AFIX 0 C22 1 0.410914 0.311300 0.262692 11.00000 0.08366 0.05103 = 0.06696 -0.00691 0.03885 0.00024 AFIX 43 H22 2 0.449219 0.284383 0.241009 11.00000 -1.20000 AFIX 0 C23 1 0.364319 0.218014 0.283438 11.00000 0.07446 0.03850 = 0.04167 -0.00520 0.00831 0.00326 C24 1 0.308633 0.254783 0.316755 11.00000 0.06636 0.03902 = 0.05568 -0.00204 0.01432 -0.01084 AFIX 43 H24 2 0.277553 0.189776 0.330609 11.00000 -1.20000 AFIX 0 C25 1 0.299416 0.390143 0.329438 11.00000 0.05344 0.04388 = 0.04950 -0.00402 0.01611 -0.00210 AFIX 43 H25 2 0.262321 0.415809 0.352571 11.00000 -1.20000 AFIX 0 CL1 3 0.377043 0.047301 0.268171 11.00000 0.12073 0.04036 = 0.06966 -0.01215 0.02205 0.00300 O1 4 0.448433 0.655369 0.422935 11.00000 0.04884 0.04121 = 0.08827 0.00771 0.01964 0.01109 O2 4 0.345560 0.767637 0.492667 11.00000 0.03940 0.04994 = 0.04733 0.01011 0.00980 0.00849 O3 4 0.270008 0.746518 0.561271 11.00000 0.07206 0.08306 = 0.05434 0.01808 0.02696 0.01377 O4 4 0.368619 0.718515 0.293171 11.00000 0.10292 0.04073 = 0.07583 0.00117 0.04993 -0.00759 C1' 1 0.572999 0.165117 0.078472 11.00000 0.03725 0.04331 = 0.05226 -0.00408 0.00584 -0.00448 C2' 1 0.646943 0.231962 0.066027 11.00000 0.03776 0.04066 = 0.04672 -0.00665 0.00940 -0.00208 C3' 1 0.626851 0.381935 0.054031 11.00000 0.04609 0.04056 = 0.05005 -0.00035 0.00861 -0.00100 AFIX 23 H3'A 2 0.663023 0.440760 0.076530 11.00000 -1.20000 H3'B 2 0.625354 0.402911 0.011999 11.00000 -1.20000 AFIX 0 C4' 1 0.550802 0.397494 0.074228 11.00000 0.03824 0.04791 = 0.03669 -0.00031 -0.00046 0.00282 C5' 1 0.520125 0.273887 0.086757 11.00000 0.03541 0.04680 = 0.04345 -0.00518 0.00055 0.00034 C6' 1 0.448470 0.264216 0.105174 11.00000 0.03795 0.06444 = 0.05591 -0.00262 0.00789 -0.00231 AFIX 43 H6' 2 0.427530 0.180789 0.112509 11.00000 -1.20000 AFIX 0 C7' 1 0.410516 0.381999 0.111950 11.00000 0.04022 0.07762 = 0.06979 -0.00659 0.01133 0.01074 AFIX 43 H7' 2 0.363362 0.378605 0.124992 11.00000 -1.20000 AFIX 0 C8' 1 0.441083 0.507161 0.099698 11.00000 0.05273 0.06511 = 0.06596 -0.00578 0.00157 0.02089 AFIX 43 H8' 2 0.413962 0.585641 0.104565 11.00000 -1.20000 AFIX 0 C9' 1 0.511102 0.516086 0.080432 11.00000 0.05234 0.05068 = 0.04971 -0.00016 -0.00370 0.01043 AFIX 43 H9' 2 0.531148 0.599493 0.071830 11.00000 -1.20000 AFIX 0 C10' 1 0.733352 0.190685 -0.005810 11.00000 0.04699 0.05025 = 0.04599 -0.00022 0.00960 0.00724 C11' 1 0.790629 0.258785 0.036693 11.00000 0.03849 0.04217 = 0.05304 0.00497 0.01087 0.00140 C12' 1 0.855023 0.309708 0.015766 11.00000 0.04609 0.05724 = 0.06813 0.01093 0.01914 -0.00095 AFIX 43 H12' 2 0.860798 0.303440 -0.024475 11.00000 -1.20000 AFIX 0 C13' 1 0.909715 0.368955 0.054628 11.00000 0.04603 0.05618 = 0.09489 0.01108 0.01932 -0.01062 AFIX 43 H13' 2 0.952247 0.404456 0.040617 11.00000 -1.20000 AFIX 0 C14' 1 0.901922 0.376078 0.114199 11.00000 0.04180 0.05235 = 0.09294 -0.00178 -0.00418 -0.01368 AFIX 43 H14' 2 0.939847 0.414515 0.140458 11.00000 -1.20000 AFIX 0 C15' 1 0.837517 0.326109 0.135802 11.00000 0.04949 0.04716 = 0.05894 -0.00529 0.00107 -0.00521 AFIX 43 H15' 2 0.832557 0.331397 0.176213 11.00000 -1.20000 AFIX 0 C16' 1 0.781135 0.268665 0.096611 11.00000 0.03623 0.03314 = 0.05334 0.00006 0.00511 -0.00199 C17' 1 0.709985 0.214865 0.117682 11.00000 0.03774 0.04038 = 0.04336 -0.00568 0.01039 -0.00244 AFIX 13 H17' 2 0.698029 0.271794 0.150747 11.00000 -1.20000 AFIX 0 C18' 1 0.720580 0.069207 0.140852 11.00000 0.04548 0.04629 = 0.04765 0.00253 0.01330 0.00252 AFIX 23 H18A 2 0.713345 0.007661 0.107262 11.00000 -1.20000 H18B 2 0.771753 0.058586 0.159459 11.00000 -1.20000 AFIX 0 C19' 1 0.667098 0.029429 0.185741 11.00000 0.06396 0.04940 = 0.04730 0.00011 0.02051 -0.00194 C20' 1 0.651307 -0.115701 0.194399 11.00000 0.05304 0.05064 = 0.03905 0.00070 0.00894 -0.00518 C21' 1 0.591738 -0.150973 0.225080 11.00000 0.06401 0.05892 = 0.05883 0.00004 0.02379 -0.00407 AFIX 43 H21' 2 0.563095 -0.083227 0.239776 11.00000 -1.20000 AFIX 0 C22' 1 0.574182 -0.284043 0.234204 11.00000 0.07429 0.06224 = 0.05831 0.00149 0.02551 -0.01835 AFIX 43 H22' 2 0.533291 -0.306568 0.253886 11.00000 -1.20000 AFIX 0 C23' 1 0.618396 -0.383569 0.213598 11.00000 0.07648 0.05065 = 0.03767 0.00311 -0.00030 -0.01675 C24' 1 0.678382 -0.352749 0.183554 11.00000 0.06654 0.04847 = 0.05662 -0.00206 0.00885 -0.00045 AFIX 43 H24' 2 0.707992 -0.420898 0.170310 11.00000 -1.20000 AFIX 0 C25' 1 0.693820 -0.218139 0.173411 11.00000 0.05276 0.05021 = 0.05915 0.00147 0.01546 0.00051 AFIX 43 H25' 2 0.733387 -0.196093 0.152156 11.00000 -1.20000 AFIX 0 CL1' 3 0.597673 -0.553160 0.224357 11.00000 0.11240 0.05218 = 0.05057 0.00435 0.00230 -0.02451 O1' 4 0.562934 0.044282 0.080494 11.00000 0.04540 0.04101 = 0.10427 -0.00515 0.01725 -0.00659 O2' 4 0.666755 0.162880 0.013504 11.00000 0.04154 0.05092 = 0.04946 -0.01234 0.00889 -0.00470 O3' 4 0.742672 0.155669 -0.055322 11.00000 0.06703 0.08889 = 0.05125 -0.01341 0.02086 0.00040 O4' 4 0.640351 0.116427 0.214723 11.00000 0.12734 0.05419 = 0.08761 -0.01009 0.06839 -0.00709 HKLF 4 REM CF solution in C2 REM R1 = 0.0392 for 6622 Fo > 4sig(Fo) and 0.0423 for all 7132 data REM 541 parameters refined using 1 restraints END WGHT 0.0652 0.6251 REM Highest difference peak 0.238, deepest hole -0.208, 1-sigma level 0.041 Q1 1 0.6529 -0.5777 0.2352 11.00000 0.05 0.24 Q2 1 0.3583 0.0766 0.2300 11.00000 0.05 0.20 Q3 1 0.2831 0.8161 0.5587 11.00000 0.05 0.15 Q4 1 0.2673 0.8591 0.4026 11.00000 0.05 0.15 Q5 1 0.6132 0.0806 0.1815 11.00000 0.05 0.15 Q6 1 0.3868 0.6843 0.3263 11.00000 0.05 0.13 Q7 1 0.7430 0.2396 0.1040 11.00000 0.05 0.13 Q8 1 0.2288 0.8769 0.4420 11.00000 0.05 0.13 Q9 1 0.2163 0.8389 0.4383 11.00000 0.05 0.13 Q10 1 0.6669 -0.3693 0.2204 11.00000 0.05 0.13 Q11 1 0.3431 1.0578 0.5341 11.00000 0.05 0.13 Q12 1 0.7734 0.3024 0.0647 11.00000 0.05 0.13 Q13 1 0.5664 -0.5896 0.1896 11.00000 0.05 0.12 Q14 1 0.6522 -0.1717 0.1636 11.00000 0.05 0.12 Q15 1 0.3684 0.2612 0.2497 11.00000 0.05 0.12 Q16 1 0.5593 -0.4223 0.1518 11.00000 0.05 0.12 Q17 1 0.8811 0.2958 0.0492 11.00000 0.05 0.12 Q18 1 0.8247 0.2040 0.2039 11.00000 0.05 0.12 Q19 1 0.5266 0.2582 0.1857 11.00000 0.05 0.12 Q20 1 0.7902 0.2401 0.0684 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0392 for 6622 Fo > 4sig(Fo) and 0.0423 for all 17206 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.24, deepest hole -0.21 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0423 REM R1_gt = 0.0392 REM wR_ref = 0.1099 REM GOOF = 1.036 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 17206 REM Reflections_gt = 6622 REM Parameters = n/a REM Hole = -0.21 REM Peak = 0.24 REM Flack = -0.007(7) ; _cod_data_source_file d0ob00541j2.cif _cod_data_source_block 20190118 _cod_original_cell_volume 3988.97(15) _cod_database_code 7157492 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C28H31ON6Cl1 _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 0.829 _shelx_estimated_absorpt_t_min 0.733 _reflns_odcompleteness_completeness 99.95 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Ternary CH refined with riding coordinates: C17(H17), C17'(H17') 2.b Secondary CH2 refined with riding coordinates: C3(H3A,H3B), C18(H18C,H18D), C3'(H3'A,H3'B), C18'(H18A,H18B) 2.c Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C8(H8), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15), C21(H21), C22(H22), C24(H24), C25(H25), C6'(H6'), C7'(H7'), C8'(H8'), C9'(H9'), C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C21'(H21'), C22'(H22'), C24'(H24'), C25'(H25') ; _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-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 C1 C 0.43586(17) 0.7751(3) 0.42372(14) 0.0418(7) Uani 1 1 d . . . . . C2 C 0.36249(16) 0.8388(3) 0.44010(13) 0.0381(6) Uani 1 1 d . . . . . C3 C 0.38202(16) 0.9890(3) 0.45242(14) 0.0421(7) Uani 1 1 d . . . . . H3A H 0.3422 1.0475 0.4345 0.050 Uiso 1 1 calc R . . . . H3B H 0.3904 1.0068 0.4949 0.050 Uiso 1 1 calc R . . . . C4 C 0.45300(16) 1.0097(3) 0.42395(13) 0.0429(7) Uani 1 1 d . . . . . C5 C 0.48399(17) 0.8876(4) 0.40929(14) 0.0432(7) Uani 1 1 d . . . . . C6 C 0.55048(18) 0.8820(4) 0.38312(17) 0.0546(8) Uani 1 1 d . . . . . H6 H 0.5715 0.7997 0.3742 0.065 Uiso 1 1 calc R . . . . C7 C 0.5836(2) 1.0018(5) 0.37109(19) 0.0676(11) Uani 1 1 d . . . . . H7 H 0.6274 1.0009 0.3528 0.081 Uiso 1 1 calc R . . . . C8 C 0.5530(2) 1.1252(5) 0.3857(2) 0.0662(11) Uani 1 1 d . . . . . H8 H 0.5767 1.2053 0.3773 0.079 Uiso 1 1 calc R . . . . C9 C 0.4876(2) 1.1299(4) 0.41270(17) 0.0551(8) Uani 1 1 d . . . . . H9 H 0.4676 1.2121 0.4230 0.066 Uiso 1 1 calc R . . . . C10 C 0.27829(18) 0.7873(3) 0.51265(14) 0.0443(7) Uani 1 1 d . . . . . C11 C 0.21942(16) 0.8558(3) 0.47229(15) 0.0420(7) Uani 1 1 d . . . . . C12 C 0.15448(19) 0.9011(4) 0.49436(18) 0.0537(8) Uani 1 1 d . . . . . H12 H 0.1484 0.8878 0.5342 0.064 Uiso 1 1 calc R . . . . C13 C 0.09944(19) 0.9653(4) 0.4572(2) 0.0624(10) Uani 1 1 d . . . . . H13 H 0.0563 0.9960 0.4720 0.075 Uiso 1 1 calc R . . . . C14 C 0.1081(2) 0.9840(4) 0.3982(2) 0.0610(10) Uani 1 1 d . . . . . H14 H 0.0706 1.0271 0.3732 0.073 Uiso 1 1 calc R . . . . C15 C 0.17179(18) 0.9397(4) 0.37561(17) 0.0514(8) Uani 1 1 d . . . . . H15 H 0.1770 0.9529 0.3356 0.062 Uiso 1 1 calc R . . . . C16 C 0.22815(16) 0.8755(3) 0.41259(14) 0.0395(6) Uani 1 1 d . . . . . C17 C 0.29815(16) 0.8234(3) 0.38926(13) 0.0380(6) Uani 1 1 d . . . . . H17 H 0.3089 0.8807 0.3560 0.046 Uiso 1 1 calc R . . . . C18 C 0.28643(18) 0.6775(3) 0.36655(15) 0.0445(7) Uani 1 1 d . . . . . H18C H 0.2951 0.6164 0.4002 0.053 Uiso 1 1 calc R . . . . H18D H 0.2346 0.6670 0.3495 0.053 Uiso 1 1 calc R . . . . C19 C 0.33664(19) 0.6360(4) 0.32028(14) 0.0470(7) Uani 1 1 d . . . . . C20 C 0.34451(19) 0.4879(3) 0.30825(13) 0.0438(7) Uani 1 1 d . . . . . C21 C 0.4001(3) 0.4462(4) 0.27452(18) 0.0632(10) Uani 1 1 d . . . . . H21 H 0.4306 0.5106 0.2596 0.076 Uiso 1 1 calc R . . . . C22 C 0.4109(3) 0.3113(4) 0.26269(18) 0.0648(10) Uani 1 1 d . . . . . H22 H 0.4492 0.2844 0.2410 0.078 Uiso 1 1 calc R . . . . C23 C 0.3643(2) 0.2180(4) 0.28344(15) 0.0514(8) Uani 1 1 d . . . . . C24 C 0.3086(2) 0.2548(4) 0.31676(16) 0.0531(8) Uani 1 1 d . . . . . H24 H 0.2776 0.1898 0.3306 0.064 Uiso 1 1 calc R . . . . C25 C 0.29942(19) 0.3901(3) 0.32944(15) 0.0481(7) Uani 1 1 d . . . . . H25 H 0.2623 0.4158 0.3526 0.058 Uiso 1 1 calc R . . . . Cl1 Cl 0.37704(8) 0.04730(10) 0.26817(5) 0.0761(3) Uani 1 1 d . . . . . O1 O 0.44843(13) 0.6554(3) 0.42294(13) 0.0585(6) Uani 1 1 d . . . . . O2 O 0.34556(12) 0.7676(2) 0.49267(10) 0.0452(5) Uani 1 1 d . . . . . O3 O 0.27001(16) 0.7465(3) 0.56127(12) 0.0683(8) Uani 1 1 d . . . . . O4 O 0.36862(19) 0.7185(3) 0.29317(13) 0.0700(8) Uani 1 1 d . . . . . C1' C 0.57300(17) 0.1651(3) 0.07847(14) 0.0442(7) Uani 1 1 d . . . . . C2' C 0.64694(17) 0.2320(3) 0.06603(14) 0.0414(7) Uani 1 1 d . . . . . C3' C 0.62685(18) 0.3819(3) 0.05403(15) 0.0453(7) Uani 1 1 d . . . . . H3'A H 0.6630 0.4408 0.0765 0.054 Uiso 1 1 calc R . . . . H3'B H 0.6254 0.4029 0.0120 0.054 Uiso 1 1 calc R . . . . C4' C 0.55080(16) 0.3975(3) 0.07423(13) 0.0413(7) Uani 1 1 d . . . . . C5' C 0.52013(17) 0.2739(4) 0.08676(14) 0.0422(7) Uani 1 1 d . . . . . C6' C 0.44847(18) 0.2642(4) 0.10517(16) 0.0526(8) Uani 1 1 d . . . . . H6' H 0.4275 0.1808 0.1125 0.063 Uiso 1 1 calc R . . . . C7' C 0.4105(2) 0.3820(5) 0.11195(19) 0.0622(10) Uani 1 1 d . . . . . H7' H 0.3634 0.3786 0.1250 0.075 Uiso 1 1 calc R . . . . C8' C 0.4411(2) 0.5072(5) 0.09970(18) 0.0617(10) Uani 1 1 d . . . . . H8' H 0.4140 0.5856 0.1046 0.074 Uiso 1 1 calc R . . . . C9' C 0.5111(2) 0.5161(4) 0.08043(15) 0.0517(8) Uani 1 1 d . . . . . H9' H 0.5311 0.5995 0.0718 0.062 Uiso 1 1 calc R . . . . C10' C 0.73335(18) 0.1907(4) -0.00581(15) 0.0474(8) Uani 1 1 d . . . . . C11' C 0.79063(17) 0.2588(3) 0.03669(15) 0.0441(7) Uani 1 1 d . . . . . C12' C 0.85502(19) 0.3097(4) 0.01577(18) 0.0562(9) Uani 1 1 d . . . . . H12' H 0.8608 0.3034 -0.0245 0.067 Uiso 1 1 calc R . . . . C13' C 0.9097(2) 0.3690(4) 0.0546(2) 0.0648(10) Uani 1 1 d . . . . . H13' H 0.9522 0.4045 0.0406 0.078 Uiso 1 1 calc R . . . . C14' C 0.9019(2) 0.3761(4) 0.1142(2) 0.0633(10) Uani 1 1 d . . . . . H14' H 0.9398 0.4145 0.1405 0.076 Uiso 1 1 calc R . . . . C15' C 0.83752(19) 0.3261(4) 0.13580(17) 0.0523(8) Uani 1 1 d . . . . . H15' H 0.8326 0.3314 0.1762 0.063 Uiso 1 1 calc R . . . . C16' C 0.78114(16) 0.2687(3) 0.09661(14) 0.0409(6) Uani 1 1 d . . . . . C17' C 0.70998(16) 0.2149(3) 0.11768(13) 0.0400(6) Uani 1 1 d . . . . . H17' H 0.6980 0.2718 0.1507 0.048 Uiso 1 1 calc R . . . . C18' C 0.72058(18) 0.0692(3) 0.14085(15) 0.0459(7) Uani 1 1 d . . . . . H18A H 0.7133 0.0077 0.1073 0.055 Uiso 1 1 calc R . . . . H18B H 0.7718 0.0586 0.1595 0.055 Uiso 1 1 calc R . . . . C19' C 0.6671(2) 0.0294(4) 0.18574(15) 0.0524(8) Uani 1 1 d . . . . . C20' C 0.65131(19) -0.1157(4) 0.19440(14) 0.0473(7) Uani 1 1 d . . . . . C21' C 0.5917(2) -0.1510(4) 0.22508(17) 0.0593(9) Uani 1 1 d . . . . . H21' H 0.5631 -0.0832 0.2398 0.071 Uiso 1 1 calc R . . . . C22' C 0.5742(2) -0.2840(4) 0.23420(17) 0.0635(10) Uani 1 1 d . . . . . H22' H 0.5333 -0.3066 0.2539 0.076 Uiso 1 1 calc R . . . . C23' C 0.6184(2) -0.3836(4) 0.21360(15) 0.0555(9) Uani 1 1 d . . . . . C24' C 0.6784(2) -0.3527(4) 0.18355(16) 0.0571(8) Uani 1 1 d . . . . . H24' H 0.7080 -0.4209 0.1703 0.069 Uiso 1 1 calc R . . . . C25' C 0.6938(2) -0.2181(4) 0.17341(16) 0.0533(8) Uani 1 1 d . . . . . H25' H 0.7334 -0.1961 0.1522 0.064 Uiso 1 1 calc R . . . . Cl1' Cl 0.59767(7) -0.55316(10) 0.22436(4) 0.0723(3) Uani 1 1 d . . . . . O1' O 0.56293(14) 0.0443(3) 0.08049(14) 0.0629(7) Uani 1 1 d . . . . . O2' O 0.66675(12) 0.1629(2) 0.01350(10) 0.0470(5) Uani 1 1 d . . . . . O3' O 0.74267(15) 0.1557(3) -0.05532(11) 0.0679(7) Uani 1 1 d . . . . . O4' O 0.6404(2) 0.1164(3) 0.21472(15) 0.0852(11) Uani 1 1 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_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0336(14) 0.0437(17) 0.0488(16) 0.0023(14) 0.0076(12) 0.0038(13) C2 0.0345(13) 0.0358(15) 0.0450(15) 0.0030(12) 0.0089(11) 0.0035(12) C3 0.0347(14) 0.0414(17) 0.0500(16) -0.0056(13) 0.0048(12) 0.0024(12) C4 0.0363(15) 0.0478(18) 0.0433(15) -0.0027(13) -0.0001(12) 0.0001(13) C5 0.0354(14) 0.0481(17) 0.0458(16) -0.0005(14) 0.0038(12) 0.0009(13) C6 0.0390(16) 0.061(2) 0.065(2) -0.0095(18) 0.0129(15) -0.0039(16) C7 0.048(2) 0.081(3) 0.078(3) -0.008(2) 0.0235(17) -0.018(2) C8 0.060(2) 0.060(2) 0.080(3) -0.001(2) 0.0159(19) -0.0249(19) C9 0.0543(19) 0.0447(19) 0.066(2) -0.0047(16) 0.0050(16) -0.0109(16) C10 0.0474(16) 0.0395(16) 0.0481(17) 0.0023(13) 0.0152(13) 0.0023(13) C11 0.0359(14) 0.0363(16) 0.0549(17) -0.0064(13) 0.0107(12) -0.0004(12) C12 0.0445(17) 0.051(2) 0.068(2) -0.0142(17) 0.0191(15) 0.0018(15) C13 0.0380(17) 0.054(2) 0.097(3) -0.018(2) 0.0145(17) 0.0053(15) C14 0.0417(18) 0.045(2) 0.094(3) -0.0057(18) -0.0057(17) 0.0078(14) C15 0.0428(16) 0.0469(18) 0.0621(19) -0.0005(16) -0.0035(14) 0.0019(15) C16 0.0335(13) 0.0333(14) 0.0515(16) -0.0030(12) 0.0043(12) 0.0000(12) C17 0.0372(14) 0.0349(15) 0.0432(15) 0.0021(12) 0.0103(12) -0.0001(12) C18 0.0465(16) 0.0383(16) 0.0510(17) -0.0029(13) 0.0149(13) -0.0042(13) C19 0.0543(18) 0.0441(18) 0.0451(16) -0.0013(14) 0.0166(13) -0.0034(15) C20 0.0535(18) 0.0408(17) 0.0390(14) -0.0020(12) 0.0136(13) -0.0047(14) C21 0.079(2) 0.0458(19) 0.073(2) -0.0036(18) 0.042(2) -0.0054(19) C22 0.084(3) 0.051(2) 0.067(2) -0.0069(18) 0.039(2) 0.000(2) C23 0.074(2) 0.0385(17) 0.0417(16) -0.0052(14) 0.0083(15) 0.0033(16) C24 0.066(2) 0.0390(17) 0.0557(19) -0.0020(15) 0.0143(16) -0.0108(16) C25 0.0534(18) 0.0439(17) 0.0495(17) -0.0040(14) 0.0161(14) -0.0021(15) Cl1 0.1207(9) 0.0404(5) 0.0697(6) -0.0122(4) 0.0220(6) 0.0030(5) O1 0.0488(13) 0.0412(13) 0.0883(18) 0.0077(13) 0.0196(12) 0.0111(11) O2 0.0394(11) 0.0499(13) 0.0473(11) 0.0101(10) 0.0098(9) 0.0085(10) O3 0.0721(17) 0.083(2) 0.0543(14) 0.0181(14) 0.0270(13) 0.0138(15) O4 0.103(2) 0.0407(14) 0.0758(18) 0.0012(13) 0.0499(16) -0.0076(14) C1' 0.0373(15) 0.0433(18) 0.0523(17) -0.0041(14) 0.0058(12) -0.0045(13) C2' 0.0378(15) 0.0407(16) 0.0467(16) -0.0067(12) 0.0094(12) -0.0021(12) C3' 0.0461(16) 0.0406(17) 0.0500(17) -0.0003(14) 0.0086(13) -0.0010(14) C4' 0.0382(15) 0.0479(17) 0.0367(14) -0.0003(13) -0.0005(11) 0.0028(13) C5' 0.0354(14) 0.0468(17) 0.0435(15) -0.0052(13) 0.0006(12) 0.0003(13) C6' 0.0380(16) 0.064(2) 0.0559(19) -0.0026(17) 0.0079(14) -0.0023(16) C7' 0.0402(17) 0.078(3) 0.070(2) -0.007(2) 0.0113(16) 0.0107(18) C8' 0.053(2) 0.065(2) 0.066(2) -0.0058(19) 0.0016(17) 0.0209(18) C9' 0.0523(18) 0.051(2) 0.0497(17) -0.0002(15) -0.0037(14) 0.0104(16) C10' 0.0470(18) 0.0502(19) 0.0460(17) -0.0002(14) 0.0096(14) 0.0072(14) C11' 0.0385(15) 0.0422(17) 0.0530(17) 0.0050(14) 0.0109(13) 0.0014(13) C12' 0.0461(17) 0.057(2) 0.068(2) 0.0109(17) 0.0191(16) -0.0009(16) C13' 0.0460(18) 0.056(2) 0.095(3) 0.011(2) 0.0193(19) -0.0106(17) C14' 0.0418(18) 0.052(2) 0.093(3) -0.002(2) -0.0042(18) -0.0137(16) C15' 0.0495(18) 0.0472(19) 0.0589(19) -0.0053(15) 0.0011(15) -0.0052(15) C16' 0.0362(14) 0.0331(14) 0.0533(17) 0.0001(13) 0.0051(12) -0.0020(12) C17' 0.0377(15) 0.0404(16) 0.0434(15) -0.0057(13) 0.0104(12) -0.0024(12) C18' 0.0455(17) 0.0463(18) 0.0476(16) 0.0025(14) 0.0133(13) 0.0025(14) C19' 0.064(2) 0.049(2) 0.0473(16) 0.0001(16) 0.0205(15) -0.0019(17) C20' 0.0530(18) 0.0506(19) 0.0390(15) 0.0007(14) 0.0089(13) -0.0052(15) C21' 0.064(2) 0.059(2) 0.059(2) 0.0000(17) 0.0238(17) -0.0041(18) C22' 0.074(3) 0.062(2) 0.058(2) 0.0015(19) 0.0255(19) -0.018(2) C23' 0.076(2) 0.051(2) 0.0377(16) 0.0031(15) -0.0003(15) -0.0168(18) C24' 0.067(2) 0.048(2) 0.057(2) -0.0021(17) 0.0088(16) -0.0004(18) C25' 0.0528(19) 0.050(2) 0.059(2) 0.0015(16) 0.0155(15) 0.0005(16) Cl1' 0.1124(8) 0.0522(5) 0.0506(5) 0.0043(4) 0.0023(5) -0.0245(6) O1' 0.0454(12) 0.0410(13) 0.104(2) -0.0052(14) 0.0172(12) -0.0066(11) O2' 0.0415(11) 0.0509(13) 0.0495(12) -0.0123(10) 0.0089(9) -0.0047(10) O3' 0.0670(15) 0.089(2) 0.0513(14) -0.0134(14) 0.0209(11) 0.0004(15) O4' 0.127(3) 0.0542(18) 0.088(2) -0.0101(15) 0.068(2) -0.0071(18) 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' Cl Cl 0.3639 0.7018 '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 C5 C1 C2 106.6(3) . . ? O1 C1 C2 124.8(3) . . ? O1 C1 C5 128.6(3) . . ? C3 C2 C1 104.7(2) . . ? C17 C2 C1 111.5(2) . . ? C17 C2 C3 111.4(2) . . ? O2 C2 C1 105.5(2) . . ? O2 C2 C3 112.7(2) . . ? O2 C2 C17 110.7(2) . . ? C2 C3 H3A 111.0 . . ? C2 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C4 C3 C2 103.8(2) . . ? C4 C3 H3A 111.0 . . ? C4 C3 H3B 111.0 . . ? C5 C4 C3 111.6(3) . . ? C9 C4 C3 128.2(3) . . ? C9 C4 C5 120.3(3) . . ? C4 C5 C1 110.1(3) . . ? C4 C5 C6 121.6(3) . . ? C6 C5 C1 128.3(3) . . ? C5 C6 H6 121.2 . . ? C7 C6 C5 117.7(4) . . ? C7 C6 H6 121.2 . . ? C6 C7 H7 119.4 . . ? C6 C7 C8 121.2(3) . . ? C8 C7 H7 119.4 . . ? C7 C8 H8 119.6 . . ? C9 C8 C7 120.8(4) . . ? C9 C8 H8 119.6 . . ? C4 C9 C8 118.4(4) . . ? C4 C9 H9 120.8 . . ? C8 C9 H9 120.8 . . ? O2 C10 C11 117.5(3) . . ? O3 C10 C11 124.4(3) . . ? O3 C10 O2 118.1(3) . . ? C12 C11 C10 119.6(3) . . ? C16 C11 C10 120.6(3) . . ? C16 C11 C12 119.8(3) . . ? C11 C12 H12 120.0 . . ? C13 C12 C11 120.0(4) . . ? C13 C12 H12 120.0 . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 120.0(3) . . ? C14 C13 H13 120.0 . . ? C13 C14 H14 119.6 . . ? C13 C14 C15 120.8(3) . . ? C15 C14 H14 119.6 . . ? C14 C15 H15 120.0 . . ? C14 C15 C16 120.0(3) . . ? C16 C15 H15 120.0 . . ? C11 C16 C17 119.1(3) . . ? C15 C16 C11 119.4(3) . . ? C15 C16 C17 121.6(3) . . ? C2 C17 H17 108.6 . . ? C2 C17 C18 113.8(3) . . ? C16 C17 C2 106.7(2) . . ? C16 C17 H17 108.6 . . ? C16 C17 C18 110.5(2) . . ? C18 C17 H17 108.6 . . ? C17 C18 H18C 108.6 . . ? C17 C18 H18D 108.6 . . ? H18C C18 H18D 107.6 . . ? C19 C18 C17 114.5(3) . . ? C19 C18 H18C 108.6 . . ? C19 C18 H18D 108.6 . . ? C20 C19 C18 117.8(3) . . ? O4 C19 C18 121.7(3) . . ? O4 C19 C20 120.5(3) . . ? C21 C20 C19 118.6(3) . . ? C25 C20 C19 123.3(3) . . ? C25 C20 C21 118.1(3) . . ? C20 C21 H21 119.3 . . ? C22 C21 C20 121.4(4) . . ? C22 C21 H21 119.3 . . ? C21 C22 H22 120.6 . . ? C23 C22 C21 118.7(4) . . ? C23 C22 H22 120.6 . . ? C22 C23 C24 121.8(3) . . ? C22 C23 Cl1 119.1(3) . . ? C24 C23 Cl1 119.1(3) . . ? C23 C24 H24 120.5 . . ? C23 C24 C25 118.9(3) . . ? C25 C24 H24 120.5 . . ? C20 C25 C24 121.0(3) . . ? C20 C25 H25 119.5 . . ? C24 C25 H25 119.5 . . ? C10 O2 C2 119.2(2) . . ? C5' C1' C2' 107.2(3) . . ? O1' C1' C2' 124.5(3) . . ? O1' C1' C5' 128.3(3) . . ? C1' C2' C3' 104.8(3) . . ? C17' C2' C1' 112.8(3) . . ? C17' C2' C3' 112.0(3) . . ? O2' C2' C1' 104.4(2) . . ? O2' C2' C3' 112.6(3) . . ? O2' C2' C17' 109.9(2) . . ? C2' C3' H3'A 110.9 . . ? C2' C3' H3'B 110.9 . . ? H3'A C3' H3'B 108.9 . . ? C4' C3' C2' 104.3(3) . . ? C4' C3' H3'A 110.9 . . ? C4' C3' H3'B 110.9 . . ? C5' C4' C3' 111.8(3) . . ? C5' C4' C9' 120.3(3) . . ? C9' C4' C3' 128.0(3) . . ? C4' C5' C1' 110.1(3) . . ? C4' C5' C6' 121.5(3) . . ? C6' C5' C1' 128.4(3) . . ? C5' C6' H6' 121.2 . . ? C7' C6' C5' 117.5(4) . . ? C7' C6' H6' 121.2 . . ? C6' C7' H7' 119.3 . . ? C6' C7' C8' 121.4(3) . . ? C8' C7' H7' 119.3 . . ? C7' C8' H8' 119.5 . . ? C9' C8' C7' 120.9(4) . . ? C9' C8' H8' 119.5 . . ? C4' C9' H9' 120.8 . . ? C8' C9' C4' 118.4(4) . . ? C8' C9' H9' 120.8 . . ? O2' C10' C11' 117.1(3) . . ? O3' C10' C11' 124.8(3) . . ? O3' C10' O2' 118.0(3) . . ? C12' C11' C10' 118.9(3) . . ? C16' C11' C10' 120.5(3) . . ? C16' C11' C12' 120.6(3) . . ? C11' C12' H12' 120.1 . . ? C13' C12' C11' 119.8(4) . . ? C13' C12' H12' 120.1 . . ? C12' C13' H13' 119.9 . . ? C12' C13' C14' 120.2(3) . . ? C14' C13' H13' 119.9 . . ? C13' C14' H14' 119.7 . . ? C13' C14' C15' 120.7(3) . . ? C15' C14' H14' 119.7 . . ? C14' C15' H15' 120.2 . . ? C16' C15' C14' 119.6(3) . . ? C16' C15' H15' 120.2 . . ? C11' C16' C17' 119.3(3) . . ? C15' C16' C11' 119.2(3) . . ? C15' C16' C17' 121.6(3) . . ? C2' C17' H17' 107.9 . . ? C2' C17' C18' 114.4(3) . . ? C16' C17' C2' 107.2(2) . . ? C16' C17' H17' 107.9 . . ? C16' C17' C18' 111.2(3) . . ? C18' C17' H17' 107.9 . . ? C17' C18' H18A 108.8 . . ? C17' C18' H18B 108.8 . . ? H18A C18' H18B 107.7 . . ? C19' C18' C17' 113.9(3) . . ? C19' C18' H18A 108.8 . . ? C19' C18' H18B 108.8 . . ? C20' C19' C18' 118.8(3) . . ? O4' C19' C18' 119.7(3) . . ? O4' C19' C20' 121.4(3) . . ? C21' C20' C19' 118.8(3) . . ? C25' C20' C19' 122.8(3) . . ? C25' C20' C21' 118.5(4) . . ? C20' C21' H21' 119.3 . . ? C22' C21' C20' 121.3(4) . . ? C22' C21' H21' 119.3 . . ? C21' C22' H22' 120.6 . . ? C21' C22' C23' 118.7(4) . . ? C23' C22' H22' 120.6 . . ? C22' C23' Cl1' 119.9(3) . . ? C24' C23' C22' 121.7(4) . . ? C24' C23' Cl1' 118.4(3) . . ? C23' C24' H24' 120.7 . . ? C23' C24' C25' 118.6(4) . . ? C25' C24' H24' 120.7 . . ? C20' C25' H25' 119.4 . . ? C24' C25' C20' 121.1(3) . . ? C24' C25' H25' 119.4 . . ? C10' O2' C2' 118.8(2) . . ? 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 C1 C2 1.545(4) . ? C1 C5 1.470(5) . ? C1 O1 1.206(4) . ? C2 C3 1.545(4) . ? C2 C17 1.537(4) . ? C2 O2 1.444(4) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C3 C4 1.509(4) . ? C4 C5 1.386(5) . ? C4 C9 1.379(5) . ? C5 C6 1.396(5) . ? C6 H6 0.9300 . ? C6 C7 1.368(6) . ? C7 H7 0.9300 . ? C7 C8 1.395(7) . ? C8 H8 0.9300 . ? C8 C9 1.387(6) . ? C9 H9 0.9300 . ? C10 C11 1.477(4) . ? C10 O2 1.353(4) . ? C10 O3 1.197(4) . ? C11 C12 1.396(4) . ? C11 C16 1.391(5) . ? C12 H12 0.9300 . ? C12 C13 1.375(6) . ? C13 H13 0.9300 . ? C13 C14 1.373(6) . ? C14 H14 0.9300 . ? C14 C15 1.379(5) . ? C15 H15 0.9300 . ? C15 C16 1.388(4) . ? C16 C17 1.511(4) . ? C17 H17 0.9800 . ? C17 C18 1.538(4) . ? C18 H18C 0.9700 . ? C18 H18D 0.9700 . ? C18 C19 1.517(4) . ? C19 C20 1.500(5) . ? C19 O4 1.207(4) . ? C20 C21 1.389(5) . ? C20 C25 1.383(5) . ? C21 H21 0.9300 . ? C21 C22 1.379(6) . ? C22 H22 0.9300 . ? C22 C23 1.366(6) . ? C23 C24 1.371(5) . ? C23 Cl1 1.744(4) . ? C24 H24 0.9300 . ? C24 C25 1.383(5) . ? C25 H25 0.9300 . ? C1' C2' 1.539(4) . ? C1' C5' 1.462(5) . ? C1' O1' 1.211(4) . ? C2' C3' 1.543(5) . ? C2' C17' 1.536(4) . ? C2' O2' 1.451(4) . ? C3' H3'A 0.9700 . ? C3' H3'B 0.9700 . ? C3' C4' 1.499(4) . ? C4' C5' 1.384(5) . ? C4' C9' 1.389(5) . ? C5' C6' 1.402(5) . ? C6' H6' 0.9300 . ? C6' C7' 1.368(6) . ? C7' H7' 0.9300 . ? C7' C8' 1.395(7) . ? C8' H8' 0.9300 . ? C8' C9' 1.382(6) . ? C9' H9' 0.9300 . ? C10' C11' 1.483(5) . ? C10' O2' 1.350(4) . ? C10' O3' 1.202(4) . ? C11' C12' 1.395(5) . ? C11' C16' 1.389(5) . ? C12' H12' 0.9300 . ? C12' C13' 1.369(6) . ? C13' H13' 0.9300 . ? C13' C14' 1.372(6) . ? C14' H14' 0.9300 . ? C14' C15' 1.398(5) . ? C15' H15' 0.9300 . ? C15' C16' 1.386(4) . ? C16' C17' 1.513(4) . ? C17' H17' 0.9800 . ? C17' C18' 1.537(5) . ? C18' H18A 0.9700 . ? C18' H18B 0.9700 . ? C18' C19' 1.530(4) . ? C19' C20' 1.481(5) . ? C19' O4' 1.215(5) . ? C20' C21' 1.387(5) . ? C20' C25' 1.386(5) . ? C21' H21' 0.9300 . ? C21' C22' 1.375(6) . ? C22' H22' 0.9300 . ? C22' C23' 1.380(6) . ? C23' C24' 1.375(6) . ? C23' Cl1' 1.742(4) . ? C24' H24' 0.9300 . ? C24' C25' 1.385(6) . ? C25' H25' 0.9300 . ? 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 C1 C2 C3 C4 17.5(3) . . . . ? C1 C2 C17 C16 174.2(2) . . . . ? C1 C2 C17 C18 52.0(3) . . . . ? C1 C2 O2 C10 -170.3(3) . . . . ? C1 C5 C6 C7 176.6(3) . . . . ? C2 C1 C5 C4 9.2(3) . . . . ? C2 C1 C5 C6 -169.0(3) . . . . ? C2 C3 C4 C5 -13.0(3) . . . . ? C2 C3 C4 C9 167.8(3) . . . . ? C2 C17 C18 C19 -84.4(3) . . . . ? C3 C2 C17 C16 -69.3(3) . . . . ? C3 C2 C17 C18 168.6(2) . . . . ? C3 C2 O2 C10 76.0(3) . . . . ? C3 C4 C5 C1 2.5(4) . . . . ? C3 C4 C5 C6 -179.1(3) . . . . ? C3 C4 C9 C8 -179.8(3) . . . . ? C4 C5 C6 C7 -1.4(5) . . . . ? C5 C1 C2 C3 -16.7(3) . . . . ? C5 C1 C2 C17 103.9(3) . . . . ? C5 C1 C2 O2 -135.8(3) . . . . ? C5 C4 C9 C8 1.0(5) . . . . ? C5 C6 C7 C8 1.4(6) . . . . ? C6 C7 C8 C9 -0.3(7) . . . . ? C7 C8 C9 C4 -0.9(6) . . . . ? C9 C4 C5 C1 -178.2(3) . . . . ? C9 C4 C5 C6 0.2(5) . . . . ? C10 C11 C12 C13 179.8(3) . . . . ? C10 C11 C16 C15 179.8(3) . . . . ? C10 C11 C16 C17 1.1(4) . . . . ? C11 C10 O2 C2 13.6(4) . . . . ? C11 C12 C13 C14 0.5(6) . . . . ? C11 C16 C17 C2 -34.5(4) . . . . ? C11 C16 C17 C18 89.7(3) . . . . ? C12 C11 C16 C15 -0.2(5) . . . . ? C12 C11 C16 C17 -178.8(3) . . . . ? C12 C13 C14 C15 -0.3(6) . . . . ? C13 C14 C15 C16 -0.1(6) . . . . ? C14 C15 C16 C11 0.3(5) . . . . ? C14 C15 C16 C17 178.9(3) . . . . ? C15 C16 C17 C2 146.9(3) . . . . ? C15 C16 C17 C18 -88.9(4) . . . . ? C16 C11 C12 C13 -0.2(5) . . . . ? C16 C17 C18 C19 155.5(3) . . . . ? C17 C2 C3 C4 -103.1(3) . . . . ? C17 C2 O2 C10 -49.4(4) . . . . ? C17 C18 C19 C20 163.5(3) . . . . ? C17 C18 C19 O4 -17.6(5) . . . . ? C18 C19 C20 C21 -168.4(3) . . . . ? C18 C19 C20 C25 11.1(5) . . . . ? C19 C20 C21 C22 179.0(4) . . . . ? C19 C20 C25 C24 179.6(3) . . . . ? C20 C21 C22 C23 1.8(7) . . . . ? C21 C20 C25 C24 -0.9(6) . . . . ? C21 C22 C23 C24 -1.6(7) . . . . ? C21 C22 C23 Cl1 179.4(4) . . . . ? C22 C23 C24 C25 0.2(6) . . . . ? C23 C24 C25 C20 1.1(6) . . . . ? C25 C20 C21 C22 -0.6(6) . . . . ? Cl1 C23 C24 C25 179.1(3) . . . . ? O1 C1 C2 C3 164.0(3) . . . . ? O1 C1 C2 C17 -75.4(4) . . . . ? O1 C1 C2 O2 44.9(4) . . . . ? O1 C1 C5 C4 -171.5(4) . . . . ? O1 C1 C5 C6 10.3(6) . . . . ? O2 C2 C3 C4 131.7(2) . . . . ? O2 C2 C17 C16 56.9(3) . . . . ? O2 C2 C17 C18 -65.2(3) . . . . ? O2 C10 C11 C12 -168.0(3) . . . . ? O2 C10 C11 C16 12.0(5) . . . . ? O3 C10 C11 C12 13.1(5) . . . . ? O3 C10 C11 C16 -166.9(4) . . . . ? O3 C10 O2 C2 -167.4(3) . . . . ? O4 C19 C20 C21 12.6(6) . . . . ? O4 C19 C20 C25 -167.9(4) . . . . ? C1' C2' C3' C4' 13.0(3) . . . . ? C1' C2' C17' C16' 172.9(3) . . . . ? C1' C2' C17' C18' 49.1(4) . . . . ? C1' C2' O2' C10' -174.1(3) . . . . ? C1' C5' C6' C7' 177.4(3) . . . . ? C2' C1' C5' C4' 6.6(3) . . . . ? C2' C1' C5' C6' -172.6(3) . . . . ? C2' C3' C4' C5' -9.8(3) . . . . ? C2' C3' C4' C9' 170.9(3) . . . . ? C2' C17' C18' C19' -83.2(3) . . . . ? C3' C2' C17' C16' -69.1(3) . . . . ? C3' C2' C17' C18' 167.1(3) . . . . ? C3' C2' O2' C10' 72.7(3) . . . . ? C3' C4' C5' C1' 2.1(4) . . . . ? C3' C4' C5' C6' -178.6(3) . . . . ? C3' C4' C9' C8' 179.8(3) . . . . ? C4' C5' C6' C7' -1.8(5) . . . . ? C5' C1' C2' C3' -12.2(3) . . . . ? C5' C1' C2' C17' 110.0(3) . . . . ? C5' C1' C2' O2' -130.8(3) . . . . ? C5' C4' C9' C8' 0.5(5) . . . . ? C5' C6' C7' C8' 1.5(6) . . . . ? C6' C7' C8' C9' -0.2(6) . . . . ? C7' C8' C9' C4' -0.8(5) . . . . ? C9' C4' C5' C1' -178.5(3) . . . . ? C9' C4' C5' C6' 0.8(5) . . . . ? C10' C11' C12' C13' -177.9(3) . . . . ? C10' C11' C16' C15' 176.4(3) . . . . ? C10' C11' C16' C17' -2.8(5) . . . . ? C11' C10' O2' C2' 17.1(4) . . . . ? C11' C12' C13' C14' 1.2(6) . . . . ? C11' C16' C17' C2' -31.1(4) . . . . ? C11' C16' C17' C18' 94.6(3) . . . . ? C12' C11' C16' C15' -2.0(5) . . . . ? C12' C11' C16' C17' 178.8(3) . . . . ? C12' C13' C14' C15' -1.5(6) . . . . ? C13' C14' C15' C16' 0.1(6) . . . . ? C14' C15' C16' C11' 1.6(5) . . . . ? C14' C15' C16' C17' -179.2(3) . . . . ? C15' C16' C17' C2' 149.7(3) . . . . ? C15' C16' C17' C18' -84.6(4) . . . . ? C16' C11' C12' C13' 0.6(5) . . . . ? C16' C17' C18' C19' 155.2(3) . . . . ? C17' C2' C3' C4' -109.7(3) . . . . ? C17' C2' O2' C10' -52.9(4) . . . . ? C17' C18' C19' C20' 157.6(3) . . . . ? C17' C18' C19' O4' -24.6(5) . . . . ? C18' C19' C20' C21' -166.6(3) . . . . ? C18' C19' C20' C25' 13.8(5) . . . . ? C19' C20' C21' C22' 179.7(4) . . . . ? C19' C20' C25' C24' 178.5(3) . . . . ? C20' C21' C22' C23' 1.8(6) . . . . ? C21' C20' C25' C24' -1.1(5) . . . . ? C21' C22' C23' C24' -1.1(6) . . . . ? C21' C22' C23' Cl1' -179.9(3) . . . . ? C22' C23' C24' C25' -0.7(6) . . . . ? C23' C24' C25' C20' 1.8(6) . . . . ? C25' C20' C21' C22' -0.7(6) . . . . ? Cl1' C23' C24' C25' 178.2(3) . . . . ? O1' C1' C2' C3' 167.6(3) . . . . ? O1' C1' C2' C17' -70.2(4) . . . . ? O1' C1' C2' O2' 49.1(4) . . . . ? O1' C1' C5' C4' -173.2(4) . . . . ? O1' C1' C5' C6' 7.5(6) . . . . ? O2' C2' C3' C4' 125.8(3) . . . . ? O2' C2' C17' C16' 56.8(3) . . . . ? O2' C2' C17' C18' -67.0(3) . . . . ? O2' C10' C11' C12' -169.3(3) . . . . ? O2' C10' C11' C16' 12.3(5) . . . . ? O3' C10' C11' C12' 12.7(6) . . . . ? O3' C10' C11' C16' -165.7(4) . . . . ? O3' C10' O2' C2' -164.8(3) . . . . ? O4' C19' C20' C21' 15.6(6) . . . . ? O4' C19' C20' C25' -164.0(4) . . . . ?