#------------------------------------------------------------------------------ #$Date: 2020-07-06 05:03:27 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253817 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/65/7126535.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_7126535 loop_ _publ_author_name 'Mando, Morgane' 'Grellepois, Fabienne' 'Riguet, Emmanuel' _publ_section_title ; Organocatalytic enantioselective allylic alkylation of \a-aryl \g-lactones: an approach to densely functionalized quaternary stereocentres. ; _journal_issue 49 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 6640 _journal_page_last 6643 _journal_paper_doi 10.1039/d0cc02058c _journal_volume 56 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C20 H26 O4 S' _chemical_formula_sum 'C20 H26 O4 S' _chemical_formula_weight 362.47 _chemical_name_systematic prism _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 mixed _atom_sites_solution_primary dual _audit_creation_date 2019-11-06 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-02-26 deposited with the CCDC. 2020-05-05 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.4331(12) _cell_length_b 15.335(3) _cell_length_c 19.485(4) _cell_measurement_reflns_used 9570 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 72.504 _cell_measurement_theta_min 3.668 _cell_volume 1922.2(7) _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 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 100.0 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0400 _diffrn_reflns_av_unetI/netI 0.0256 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 22927 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.590 _diffrn_reflns_theta_min 3.668 _exptl_absorpt_coefficient_mu 1.665 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_correction_T_min 0.6810 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0854 before and 0.0716 after correction. The Ratio of minimum to maximum transmission is 0.9037. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.252 _exptl_crystal_description prism _exptl_crystal_F_000 776 _exptl_crystal_size_max 0.374 _exptl_crystal_size_mid 0.308 _exptl_crystal_size_min 0.29 _refine_diff_density_max 0.206 _refine_diff_density_min -0.157 _refine_diff_density_rms 0.033 _refine_ls_abs_structure_details ; Flack x determined using 1503 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.074(6) _refine_ls_extinction_coef 0.0019(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)' _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 259 _refine_ls_number_reflns 3782 _refine_ls_number_restraints 4 _refine_ls_restrained_S_all 1.086 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0263 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0252P)^2^+0.4483P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.0637 _reflns_Friedel_coverage 0.725 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.989 _reflns_number_gt 3668 _reflns_number_total 3782 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc02058c2.cif _cod_data_source_block cu_19er014_0m_a _cod_depositor_comments 'Adding full bibliography for 7126535.cif.' _cod_original_cell_volume 1922.2(6) _cod_database_code 7126535 _shelx_shelxl_version_number 2017/1 _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 0.644 _shelx_estimated_absorpt_t_min 0.575 _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. Restrained distances S1B-C13 = S1B-C20B 1.74 with sigma of 0.001 S1A-C13 = S1A-C20A 1.74 with sigma of 0.001 3. Uiso/Uaniso restraints and constraints Uanis(C19A) = Uanis(C18A) = Uanis(C17A) = Uanis(C16A) Uanis(C16B) = Uanis(C17B) = Uanis(C18B) = Uanis(C16A) Uanis(C15A) = Uanis(C20B) = Uanis(C15B) = Uanis(C20A) 4. Others Sof(S1A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(C16A)=Sof(H16A)=Sof(C17A)= Sof(H17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=1-FVAR(1) Sof(S1B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(C16B)=Sof(H16B)=Sof(C17B)= Sof(H17B)=Sof(C18B)=Sof(H18B)=Sof(C19B)=Sof(H19B)=Sof(C20B)=FVAR(1) 5.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B) 5.b Aromatic/amide H refined with riding coordinates: C14B(H14B), C16B(H16B), C17B(H17B), C18B(H18B), C19B(H19B), C14A(H14A), C16A(H16A), C17A(H17A), C18A(H18A), C19A(H19A) 5.c Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C3(H3A,H3B,H3C), C4(H4A,H4B,H4C) 5.d Idealised tetrahedral OH refined as rotating group: O1(H1), O2(H2) ; _shelx_res_file ; TITL cu_19er014_0m_a_a.res in P2(1)2(1)2(1) cu_19er014_0m_a.res created by SHELXL-2017/1 at 15:32:05 on 06-Nov-2019 REM Old TITL cu_19ER014_0m_a.res in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1) REM R1 0.145, Rweak 0.031, Alpha 0.001, Orientation as input REM Flack x = 0.157 ( 0.007 ) from Parsons' quotients REM Formula found by SHELXT: C17B O5 S2 CELL 1.54178 6.4331 15.3346 19.4853 90 90 90 ZERR 4 0.0012 0.0029 0.0036 0 0 0 LATT -1 SYMM 0.5-X,-Y,0.5+Z SYMM -X,0.5+Y,0.5-Z SYMM 0.5+X,0.5-Y,-Z SFAC C H O S UNIT 80 104 16 4 DFIX 1.74 0.001 S1B C13 S1B C20B DFIX 1.74 0.001 S1A C13 S1A C20A EADP C19A C18A C17A C16A EADP C16B C17B C18B C16A EADP C15A C20B C15B C20A L.S. 99 PLAN 5 SIZE 0.29 0.308 0.374 TEMP -173.15 list 4 fmap 2 acta REM REM REM WGHT 0.025200 0.448300 EXTI 0.001886 FVAR 0.74451 0.59236 O1 3 0.841348 0.247288 0.571882 11.00000 0.01631 0.02008 = 0.02225 -0.00808 -0.00066 0.00206 AFIX 147 H1 2 0.792716 0.220555 0.537852 11.00000 -1.50000 AFIX 0 O2 3 0.176868 0.339040 0.536494 11.00000 0.01708 0.02527 = 0.02044 -0.01043 0.00168 -0.00525 AFIX 147 H2 2 0.069366 0.309329 0.543707 11.00000 -1.50000 AFIX 0 O3 3 0.509910 0.676001 0.582720 11.00000 0.02380 0.02448 = 0.03231 -0.00602 0.00248 -0.00435 O4 3 0.185625 0.692980 0.626054 11.00000 0.02771 0.01531 = 0.02956 -0.00435 0.00717 -0.00116 C1 1 0.021582 0.801864 0.689729 11.00000 0.06673 0.02565 = 0.07823 -0.01241 0.03912 0.00342 AFIX 137 H1A 2 -0.085289 0.803715 0.653918 11.00000 -1.50000 H1B 2 0.031371 0.859067 0.711922 11.00000 -1.50000 H1C 2 -0.015646 0.757737 0.723971 11.00000 -1.50000 AFIX 0 C2 1 0.228739 0.778840 0.657922 11.00000 0.04619 0.01339 = 0.02987 -0.00495 0.01235 -0.00203 C3 1 0.398196 0.769098 0.711342 11.00000 0.07461 0.02597 = 0.02244 -0.00595 0.00050 -0.01049 AFIX 137 H3A 2 0.357058 0.724807 0.744958 11.00000 -1.50000 H3B 2 0.419448 0.824988 0.734701 11.00000 -1.50000 H3C 2 0.527722 0.751197 0.688929 11.00000 -1.50000 AFIX 0 C4 1 0.287181 0.844280 0.602447 11.00000 0.06047 0.01680 = 0.03401 0.00122 0.00446 -0.00173 AFIX 137 H4A 2 0.426247 0.830725 0.584905 11.00000 -1.50000 H4B 2 0.286669 0.903237 0.621855 11.00000 -1.50000 H4C 2 0.186252 0.841011 0.564862 11.00000 -1.50000 AFIX 0 C5 1 0.331769 0.652726 0.588844 11.00000 0.02287 0.01701 = 0.01629 0.00212 -0.00054 0.00090 C6 1 0.246076 0.574187 0.552609 11.00000 0.02418 0.01624 = 0.01492 0.00151 -0.00148 -0.00062 C7 1 0.046262 0.571961 0.534282 11.00000 0.02624 0.02344 = 0.02702 0.00080 -0.00640 -0.00058 H7A 2 -0.053706 0.618272 0.546743 11.00000 0.02688 H7B 2 -0.004556 0.523326 0.504343 11.00000 0.03188 C8 1 0.402058 0.505599 0.532715 11.00000 0.02342 0.01775 = 0.01463 -0.00162 0.00006 -0.00139 AFIX 23 H8A 2 0.536189 0.534657 0.522847 11.00000 -1.20000 H8B 2 0.354602 0.477479 0.489748 11.00000 -1.20000 AFIX 0 C9 1 0.440076 0.433195 0.587445 11.00000 0.01575 0.01539 = 0.01308 -0.00274 0.00083 -0.00097 C10 1 0.240767 0.379891 0.598745 11.00000 0.01496 0.01921 = 0.01431 -0.00441 -0.00031 0.00026 AFIX 23 H10A 2 0.266026 0.334851 0.634177 11.00000 -1.20000 H10B 2 0.128767 0.418758 0.615433 11.00000 -1.20000 AFIX 0 C11 1 0.617682 0.375106 0.559018 11.00000 0.01464 0.01714 = 0.01437 -0.00327 0.00191 -0.00142 AFIX 23 H11A 2 0.574847 0.352689 0.513519 11.00000 -1.20000 H11B 2 0.741828 0.412182 0.551940 11.00000 -1.20000 AFIX 0 C12 1 0.679750 0.298056 0.603508 11.00000 0.01967 0.01602 = 0.02029 -0.00165 0.00510 0.00133 AFIX 23 H12A 2 0.728714 0.319576 0.648599 11.00000 -1.20000 H12B 2 0.556769 0.260590 0.611478 11.00000 -1.20000 AFIX 0 C13 1 0.502538 0.473598 0.656141 11.00000 0.01339 0.01398 = 0.01345 -0.00156 0.00043 0.00070 PART 1 S1B 4 0.753575 0.515186 0.666252 21.00000 0.01413 0.02035 = 0.01289 -0.00656 -0.00006 -0.00143 C14B 1 0.392379 0.485647 0.713259 21.00000 0.01877 0.02298 = 0.03455 -0.00121 -0.00791 -0.00348 AFIX 43 H14B 2 0.251401 0.467766 0.716813 21.00000 -1.20000 AFIX 0 C15B 1 0.496892 0.526404 0.768060 21.00000 0.02103 0.01341 = 0.01482 -0.00185 -0.00204 0.00314 C16B 1 0.425963 0.547706 0.834252 21.00000 0.02229 0.01841 = 0.01382 -0.00335 -0.00201 0.00139 AFIX 43 H16B 2 0.287845 0.534128 0.847797 21.00000 -1.20000 AFIX 0 C17B 1 0.559978 0.588634 0.879250 21.00000 0.02229 0.01841 = 0.01382 -0.00335 -0.00201 0.00139 AFIX 43 H17B 2 0.513564 0.602307 0.924266 21.00000 -1.20000 AFIX 0 C18B 1 0.762244 0.610297 0.859878 21.00000 0.02229 0.01841 = 0.01382 -0.00335 -0.00201 0.00139 AFIX 43 H18B 2 0.850251 0.639087 0.891807 21.00000 -1.20000 AFIX 0 C19B 1 0.837121 0.590820 0.795406 21.00000 0.02035 0.01884 = 0.02247 -0.00482 -0.00474 -0.00073 AFIX 43 H19B 2 0.975140 0.605248 0.782301 21.00000 -1.20000 AFIX 0 C20B 1 0.700331 0.548617 0.749770 21.00000 0.02103 0.01341 = 0.01482 -0.00185 -0.00204 0.00314 PART 0 PART 2 S1A 4 0.315667 0.481748 0.720772 -21.00000 0.01787 0.02280 = 0.01081 -0.00538 -0.00198 -0.00214 C14A 1 0.673554 0.505720 0.675841 -21.00000 0.02615 0.03883 = 0.03298 0.00454 0.02017 0.00498 AFIX 43 H14A 2 0.790243 0.506225 0.645963 -21.00000 -1.20000 AFIX 0 C15A 1 0.689453 0.540772 0.742546 -21.00000 0.02103 0.01341 = 0.01482 -0.00185 -0.00204 0.00314 C16A 1 0.848022 0.581734 0.779198 -21.00000 0.02229 0.01841 = 0.01382 -0.00335 -0.00201 0.00139 AFIX 43 H16A 2 0.980117 0.589496 0.758276 -21.00000 -1.20000 AFIX 0 C17A 1 0.816843 0.610884 0.844610 -21.00000 0.02229 0.01841 = 0.01382 -0.00335 -0.00201 0.00139 AFIX 43 H17A 2 0.926569 0.639266 0.868396 -21.00000 -1.20000 AFIX 0 C18A 1 0.626581 0.599391 0.876521 -21.00000 0.02229 0.01841 = 0.01382 -0.00335 -0.00201 0.00139 AFIX 43 H18A 2 0.609601 0.618584 0.922537 -21.00000 -1.20000 AFIX 0 C19A 1 0.460217 0.560667 0.843202 -21.00000 0.02229 0.01841 = 0.01382 -0.00335 -0.00201 0.00139 AFIX 43 H19A 2 0.329845 0.553301 0.865355 -21.00000 -1.20000 AFIX 0 C20A 1 0.492047 0.532715 0.775307 -21.00000 0.02103 0.01341 = 0.01482 -0.00185 -0.00204 0.00314 HKLF 4 REM cu_19er014_0m_a_a.res in P2(1)2(1)2(1) REM R1 = 0.0263 for 3668 Fo > 4sig(Fo) and 0.0275 for all 3782 data REM 259 parameters refined using 4 restraints END WGHT 0.0252 0.4483 REM Highest difference peak 0.206, deepest hole -0.157, 1-sigma level 0.033 Q1 1 0.4753 0.4531 0.6289 11.00000 0.05 0.21 Q2 1 0.5134 0.3952 0.5732 11.00000 0.05 0.18 Q3 1 0.5996 0.5360 0.7589 11.00000 0.05 0.17 Q4 1 0.3345 0.4100 0.5956 11.00000 0.05 0.16 Q5 1 0.2850 0.6025 0.5779 11.00000 0.05 0.16 ; _shelx_res_checksum 26100 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.84135(19) 0.24729(8) 0.57188(6) 0.0195(3) Uani 1 1 d . . . . . H1 H 0.792716 0.220555 0.537852 0.029 Uiso 1 1 calc GR . . . . O2 O 0.1769(2) 0.33904(8) 0.53649(6) 0.0209(3) Uani 1 1 d . . . . . H2 H 0.069366 0.309329 0.543707 0.031 Uiso 1 1 calc GR . . . . O3 O 0.5099(2) 0.67600(9) 0.58272(7) 0.0269(3) Uani 1 1 d . . . . . O4 O 0.1856(2) 0.69298(8) 0.62605(7) 0.0242(3) Uani 1 1 d . . . . . C1 C 0.0216(5) 0.80186(16) 0.68973(17) 0.0569(8) Uani 1 1 d . . . . . H1A H -0.085289 0.803715 0.653918 0.085 Uiso 1 1 calc GR . . . . H1B H 0.031371 0.859067 0.711922 0.085 Uiso 1 1 calc GR . . . . H1C H -0.015646 0.757737 0.723971 0.085 Uiso 1 1 calc GR . . . . C2 C 0.2287(4) 0.77884(11) 0.65792(10) 0.0298(5) Uani 1 1 d . . . . . C3 C 0.3982(5) 0.76910(15) 0.71134(11) 0.0410(6) Uani 1 1 d . . . . . H3A H 0.357058 0.724807 0.744958 0.062 Uiso 1 1 calc GR . . . . H3B H 0.419448 0.824988 0.734701 0.062 Uiso 1 1 calc GR . . . . H3C H 0.527722 0.751197 0.688929 0.062 Uiso 1 1 calc GR . . . . C4 C 0.2872(4) 0.84428(13) 0.60245(11) 0.0371(5) Uani 1 1 d . . . . . H4A H 0.426247 0.830725 0.584905 0.056 Uiso 1 1 calc GR . . . . H4B H 0.286669 0.903237 0.621855 0.056 Uiso 1 1 calc GR . . . . H4C H 0.186252 0.841011 0.564862 0.056 Uiso 1 1 calc GR . . . . C5 C 0.3318(3) 0.65273(11) 0.58884(9) 0.0187(4) Uani 1 1 d . . . . . C6 C 0.2461(3) 0.57419(11) 0.55261(8) 0.0184(3) Uani 1 1 d . . . . . C7 C 0.0463(3) 0.57196(13) 0.53428(10) 0.0256(4) Uani 1 1 d . . . . . H7A H -0.054(4) 0.6183(16) 0.5467(12) 0.027(6) Uiso 1 1 d . . . . . H7B H -0.005(4) 0.5233(16) 0.5043(12) 0.032(6) Uiso 1 1 d . . . . . C8 C 0.4021(3) 0.50560(12) 0.53272(8) 0.0186(4) Uani 1 1 d . . . . . H8A H 0.536189 0.534657 0.522847 0.022 Uiso 1 1 calc R . . . . H8B H 0.354602 0.477479 0.489748 0.022 Uiso 1 1 calc R . . . . C9 C 0.4401(3) 0.43320(11) 0.58744(8) 0.0147(3) Uani 1 1 d . . . . . C10 C 0.2408(3) 0.37989(11) 0.59874(8) 0.0162(3) Uani 1 1 d . . . . . H10A H 0.266026 0.334851 0.634177 0.019 Uiso 1 1 calc R . . . . H10B H 0.128767 0.418758 0.615433 0.019 Uiso 1 1 calc R . . . . C11 C 0.6177(3) 0.37511(11) 0.55902(9) 0.0154(3) Uani 1 1 d . . . . . H11A H 0.574847 0.352689 0.513519 0.018 Uiso 1 1 calc R . . . . H11B H 0.741828 0.412182 0.551940 0.018 Uiso 1 1 calc R . . . . C12 C 0.6798(3) 0.29806(11) 0.60351(9) 0.0187(4) Uani 1 1 d . . . . . H12A H 0.728714 0.319576 0.648599 0.022 Uiso 1 1 calc R . . . . H12B H 0.556769 0.260590 0.611478 0.022 Uiso 1 1 calc R . . . . C13 C 0.5025(2) 0.47360(10) 0.65614(7) 0.0136(3) Uani 1 1 d D . . . . S1B S 0.75358(18) 0.51519(7) 0.66625(5) 0.0158(3) Uani 0.592(3) 1 d D . P A 1 C14B C 0.3924(9) 0.4856(4) 0.7133(3) 0.0254(13) Uani 0.592(3) 1 d . . P A 1 H14B H 0.251401 0.467766 0.716813 0.031 Uiso 0.592(3) 1 calc R . P A 1 C15B C 0.4969(10) 0.5264(9) 0.7681(4) 0.0164(4) Uani 0.592(3) 1 d . . P A 1 C16B C 0.4260(8) 0.5477(3) 0.8343(2) 0.0182(4) Uani 0.592(3) 1 d . . P A 1 H16B H 0.287845 0.534128 0.847797 0.022 Uiso 0.592(3) 1 calc R . P A 1 C17B C 0.5600(6) 0.5886(2) 0.87925(19) 0.0182(4) Uani 0.592(3) 1 d . . P A 1 H17B H 0.513564 0.602307 0.924266 0.022 Uiso 0.592(3) 1 calc R . P A 1 C18B C 0.7622(7) 0.6103(2) 0.85988(18) 0.0182(4) Uani 0.592(3) 1 d . . P A 1 H18B H 0.850251 0.639087 0.891807 0.022 Uiso 0.592(3) 1 calc R . P A 1 C19B C 0.8371(10) 0.5908(3) 0.7954(2) 0.0206(12) Uani 0.592(3) 1 d . . P A 1 H19B H 0.975140 0.605248 0.782301 0.025 Uiso 0.592(3) 1 calc R . P A 1 C20B C 0.7003(12) 0.5486(8) 0.7498(3) 0.0164(4) Uani 0.592(3) 1 d D . P A 1 S1A S 0.3157(3) 0.48175(15) 0.72077(9) 0.0172(5) Uani 0.408(3) 1 d D . P A 2 C14A C 0.6736(15) 0.5057(6) 0.6758(4) 0.033(2) Uani 0.408(3) 1 d . . P A 2 H14A H 0.790243 0.506225 0.645963 0.039 Uiso 0.408(3) 1 calc R . P A 2 C15A C 0.6895(18) 0.5408(12) 0.7425(4) 0.0164(4) Uani 0.408(3) 1 d . . P A 2 C16A C 0.8480(18) 0.5817(6) 0.7792(5) 0.0182(4) Uani 0.408(3) 1 d . . P A 2 H16A H 0.980117 0.589496 0.758276 0.022 Uiso 0.408(3) 1 calc R . P A 2 C17A C 0.8168(9) 0.6109(4) 0.8446(3) 0.0182(4) Uani 0.408(3) 1 d . . P A 2 H17A H 0.926569 0.639266 0.868396 0.022 Uiso 0.408(3) 1 calc R . P A 2 C18A C 0.6266(9) 0.5994(4) 0.8765(3) 0.0182(4) Uani 0.408(3) 1 d . . P A 2 H18A H 0.609601 0.618584 0.922537 0.022 Uiso 0.408(3) 1 calc R . P A 2 C19A C 0.4602(12) 0.5607(4) 0.8432(3) 0.0182(4) Uani 0.408(3) 1 d . . P A 2 H19A H 0.329845 0.553301 0.865355 0.022 Uiso 0.408(3) 1 calc R . P A 2 C20A C 0.4920(14) 0.5327(13) 0.7753(6) 0.0164(4) Uani 0.408(3) 1 d D . P A 2 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 0.0163(6) 0.0201(6) 0.0223(6) -0.0081(5) -0.0007(5) 0.0021(5) O2 0.0171(6) 0.0253(7) 0.0204(6) -0.0104(5) 0.0017(5) -0.0052(5) O3 0.0238(7) 0.0245(7) 0.0323(7) -0.0060(6) 0.0025(6) -0.0043(6) O4 0.0277(7) 0.0153(6) 0.0296(7) -0.0044(5) 0.0072(6) -0.0012(5) C1 0.0667(18) 0.0256(12) 0.0782(19) -0.0124(13) 0.0391(16) 0.0034(12) C2 0.0462(12) 0.0134(8) 0.0299(10) -0.0049(7) 0.0124(10) -0.0020(8) C3 0.0746(17) 0.0260(11) 0.0224(10) -0.0060(8) 0.0005(11) -0.0105(11) C4 0.0605(16) 0.0168(9) 0.0340(11) 0.0012(8) 0.0045(11) -0.0017(10) C5 0.0229(9) 0.0170(8) 0.0163(8) 0.0021(7) -0.0005(7) 0.0009(7) C6 0.0242(8) 0.0162(8) 0.0149(7) 0.0015(6) -0.0015(7) -0.0006(7) C7 0.0262(10) 0.0234(10) 0.0270(10) 0.0008(8) -0.0064(8) -0.0006(8) C8 0.0234(9) 0.0177(9) 0.0146(7) -0.0016(7) 0.0001(6) -0.0014(7) C9 0.0158(8) 0.0154(8) 0.0131(7) -0.0027(6) 0.0008(6) -0.0010(7) C10 0.0150(8) 0.0192(8) 0.0143(8) -0.0044(6) -0.0003(6) 0.0003(7) C11 0.0146(8) 0.0171(8) 0.0144(7) -0.0033(7) 0.0019(6) -0.0014(6) C12 0.0197(8) 0.0160(8) 0.0203(8) -0.0017(7) 0.0051(7) 0.0013(7) C13 0.0134(8) 0.0140(8) 0.0135(7) -0.0016(6) 0.0004(6) 0.0007(6) S1B 0.0141(6) 0.0204(4) 0.0129(4) -0.0066(3) -0.0001(4) -0.0014(4) C14B 0.019(3) 0.023(2) 0.035(3) -0.0012(18) -0.008(2) -0.003(3) C15B 0.0210(7) 0.0134(17) 0.0148(12) -0.0019(9) -0.0020(7) 0.0031(6) C16B 0.0223(13) 0.0184(7) 0.0138(7) -0.0033(5) -0.0020(6) 0.0014(8) C17B 0.0223(13) 0.0184(7) 0.0138(7) -0.0033(5) -0.0020(6) 0.0014(8) C18B 0.0223(13) 0.0184(7) 0.0138(7) -0.0033(5) -0.0020(6) 0.0014(8) C19B 0.0204(18) 0.019(2) 0.022(3) -0.0048(18) -0.005(2) -0.0007(15) C20B 0.0210(7) 0.0134(17) 0.0148(12) -0.0019(9) -0.0020(7) 0.0031(6) S1A 0.0179(11) 0.0228(6) 0.0108(6) -0.0054(5) -0.0020(6) -0.0021(7) C14A 0.026(4) 0.039(4) 0.033(4) 0.005(3) 0.020(3) 0.005(4) C15A 0.0210(7) 0.0134(17) 0.0148(12) -0.0019(9) -0.0020(7) 0.0031(6) C16A 0.0223(13) 0.0184(7) 0.0138(7) -0.0033(5) -0.0020(6) 0.0014(8) C17A 0.0223(13) 0.0184(7) 0.0138(7) -0.0033(5) -0.0020(6) 0.0014(8) C18A 0.0223(13) 0.0184(7) 0.0138(7) -0.0033(5) -0.0020(6) 0.0014(8) C19A 0.0223(13) 0.0184(7) 0.0138(7) -0.0033(5) -0.0020(6) 0.0014(8) C20A 0.0210(7) 0.0134(17) 0.0148(12) -0.0019(9) -0.0020(7) 0.0031(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' S S 0.3331 0.5567 '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 O4 C2 120.36(15) . . ? O4 C2 C1 102.38(17) . . ? O4 C2 C3 109.57(16) . . ? O4 C2 C4 109.54(15) . . ? C1 C2 C3 112.1(2) . . ? C1 C2 C4 110.8(2) . . ? C3 C2 C4 112.0(2) . . ? O3 C5 O4 125.78(17) . . ? O3 C5 C6 122.67(17) . . ? O4 C5 C6 111.53(15) . . ? C5 C6 C8 115.92(16) . . ? C7 C6 C5 120.01(17) . . ? C7 C6 C8 123.75(17) . . ? C6 C8 C9 115.24(14) . . ? C10 C9 C8 110.25(14) . . ? C10 C9 C11 111.12(13) . . ? C11 C9 C8 106.28(13) . . ? C13 C9 C8 110.59(13) . . ? C13 C9 C10 108.03(12) . . ? C13 C9 C11 110.60(13) . . ? O2 C10 C9 110.64(13) . . ? C12 C11 C9 115.89(14) . . ? O1 C12 C11 111.51(14) . . ? C9 C13 S1B 119.31(10) . . ? C9 C13 S1A 118.67(12) . . ? C14B C13 C9 130.4(2) . . ? C14B C13 S1B 110.3(3) . . ? C14A C13 C9 130.7(3) . . ? C14A C13 S1A 110.6(3) . . ? C20B S1B C13 91.8(2) . . ? C13 C14B C15B 116.2(5) . . ? C16B C15B C14B 130.1(6) . . ? C20B C15B C14B 111.2(5) . . ? C20B C15B C16B 118.7(3) . . ? C17B C16B C15B 119.0(4) . . ? C16B C17B C18B 121.3(3) . . ? C19B C18B C17B 121.4(4) . . ? C18B C19B C20B 117.2(5) . . ? C15B C20B S1B 110.5(4) . . ? C15B C20B C19B 122.4(3) . . ? C19B C20B S1B 127.1(4) . . ? C20A S1A C13 91.4(3) . . ? C13 C14A C15A 119.4(7) . . ? C14A C15A C20A 108.3(7) . . ? C16A C15A C14A 134.2(9) . . ? C16A C15A C20A 117.4(6) . . ? C17A C16A C15A 121.2(10) . . ? C16A C17A C18A 120.5(7) . . ? C17A C18A C19A 121.8(5) . . ? C18A C19A C20A 117.3(7) . . ? C15A C20A S1A 110.2(6) . . ? C19A C20A S1A 128.1(7) . . ? C19A C20A C15A 121.6(5) . . ? 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 C12 1.438(2) . ? O2 C10 1.426(2) . ? O3 C5 1.206(2) . ? O4 C2 1.482(2) . ? O4 C5 1.338(2) . ? C1 C2 1.512(3) . ? C2 C3 1.515(3) . ? C2 C4 1.522(3) . ? C5 C6 1.501(2) . ? C6 C7 1.335(3) . ? C6 C8 1.504(2) . ? C8 C9 1.559(2) . ? C9 C10 1.536(2) . ? C9 C11 1.551(2) . ? C9 C13 1.529(2) . ? C11 C12 1.519(2) . ? C13 S1B 1.7474(12) . ? C13 C14B 1.332(7) . ? C13 S1A 1.7455(12) . ? C13 C14A 1.265(10) . ? S1B C20B 1.7403(14) . ? C14B C15B 1.408(6) . ? C15B C16B 1.407(8) . ? C15B C20B 1.399(10) . ? C16B C17B 1.381(4) . ? C17B C18B 1.395(5) . ? C18B C19B 1.378(5) . ? C19B C20B 1.409(7) . ? S1A C20A 1.7400(14) . ? C14A C15A 1.410(9) . ? C15A C16A 1.395(14) . ? C15A C20A 1.427(14) . ? C16A C17A 1.365(8) . ? C17A C18A 1.384(7) . ? C18A C19A 1.385(6) . ? C19A C20A 1.406(11) . ?