#------------------------------------------------------------------------------ #$Date: 2024-10-25 01:10:41 +0300 (Fri, 25 Oct 2024) $ #$Revision: 295609 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/29/1572942.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_1572942 loop_ _publ_author_name 'St\"uhler, Merlin R.' 'Kreische, Marie' 'Fornacon-Wood, Christoph' 'Rupf, Susanne M.' 'Langer, Robert' 'Plajer, Alex Johannes' _publ_section_title ; Monomer centred selectivity guidelines in sulfurated ring-opening copolymerisations ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC05858E _journal_year 2024 _chemical_formula_moiety 'C11 H10 O2 S2' _chemical_formula_sum 'C11 H10 O2 S2' _chemical_formula_weight 238.31 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2024-08-13 _audit_creation_method ; Olex2 1.3 (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _audit_update_record ; 2024-08-13 deposited with the CCDC. 2024-10-24 downloaded from the CCDC. ; _cell_angle_alpha 90.902(2) _cell_angle_beta 99.837(2) _cell_angle_gamma 110.120(2) _cell_formula_units_Z 4 _cell_length_a 8.5111(3) _cell_length_b 11.2673(4) _cell_length_c 12.0154(5) _cell_measurement_reflns_used 9994 _cell_measurement_temperature 100 _cell_measurement_theta_max 26.38 _cell_measurement_theta_min 2.48 _cell_volume 1062.56(7) _computing_cell_refinement 'SAINT V8.38A (Bruker, 2018)' _computing_data_reduction 'SAINT V8.38A (Bruker, 2018)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0655 _diffrn_reflns_av_unetI/netI 0.0331 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 34242 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.393 _diffrn_reflns_theta_min 1.931 _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.475 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6641 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1187 before and 0.0698 after correction. The Ratio of minimum to maximum transmission is 0.8909. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.490 _exptl_crystal_description plate _exptl_crystal_F_000 496 _exptl_crystal_recrystallization_method 'recrystallization from ethyl acetate' _exptl_crystal_size_max 0.351 _exptl_crystal_size_mid 0.165 _exptl_crystal_size_min 0.137 _refine_diff_density_max 0.807 _refine_diff_density_min -0.343 _refine_diff_density_rms 0.073 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.114 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 4349 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.114 _refine_ls_R_factor_all 0.0609 _refine_ls_R_factor_gt 0.0381 _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^)+(0.0264P)^2^+1.5643P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0812 _refine_ls_wR_factor_ref 0.0999 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3404 _reflns_number_total 4349 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc05858e2.cif _cod_data_source_block p-1 _cod_database_code 1572942 _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 0.938 _shelx_estimated_absorpt_t_min 0.851 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C12(H12), C21(H21) 2.b Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C22(H22A,H22B) 2.c Aromatic/amide H refined with riding coordinates: C5(H5), C7(H7), C8(H8), C10(H10), C13(H13), C16(H16), C19(H19), C20(H20) 2.d Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C18(H18A,H18B,H18C) ; _shelx_res_file ; TITL p-1_a.res in P-1 p-1.res created by SHELXL-2018/3 at 10:39:18 on 13-Aug-2024 REM Old TITL P-1 in P-1 #2 REM SHELXT solution in P-1 REM R1 0.108, Rweak 0.001, Alpha 0.017, Orientation as input REM Formula found by SHELXT: C22 O4 S4 CELL 0.71073 8.5111 11.2673 12.0154 90.902 99.837 110.12 ZERR 4 0.0003 0.0004 0.0005 0.002 0.002 0.002 LATT 1 SFAC C H O S UNIT 44 40 8 8 L.S. 4 PLAN 1 SIZE 0.137 0.165 0.351 TEMP -173.15 CONF BOND $H list 4 MORE -1 fmap 2 acta REM REM REM WGHT 0.026400 1.564300 FVAR 0.54297 S1 4 0.801984 0.451941 0.662769 11.00000 0.02567 0.02426 = 0.01939 0.00276 0.00341 0.00972 S2 4 0.672185 0.351300 0.425304 11.00000 0.03422 0.02247 = 0.01979 0.00159 0.00588 0.00904 S3 4 0.213589 0.792616 0.833535 11.00000 0.02811 0.02861 = 0.01913 -0.00096 0.00149 0.01251 S4 4 0.320374 0.765393 1.074174 11.00000 0.03796 0.03629 = 0.01884 0.00123 0.00442 0.02118 O1 3 0.527099 0.797608 0.923275 11.00000 0.02208 0.02175 = 0.03154 -0.00278 0.00512 0.00544 O2 3 0.269789 0.127493 0.633806 11.00000 0.02313 0.03237 = 0.03033 0.00072 0.00976 0.00710 O3 3 0.483922 0.288755 0.586946 11.00000 0.02149 0.02542 = 0.02882 0.00483 0.00719 0.01006 O4 3 0.741358 0.747929 0.874641 11.00000 0.02332 0.03378 = 0.03900 0.00329 0.01020 0.00704 C1 1 0.691114 0.195038 0.601281 11.00000 0.02411 0.02328 = 0.01769 0.00245 0.00298 0.01054 C2 1 0.464621 0.585572 0.874605 11.00000 0.02479 0.02489 = 0.01429 0.00310 0.00476 0.00921 C3 1 0.545933 0.109423 0.629378 11.00000 0.02392 0.02416 = 0.01626 0.00085 0.00382 0.00768 C4 1 0.414614 0.168324 0.619487 11.00000 0.02629 0.02314 = 0.01805 0.00155 0.00722 0.00644 C5 1 0.537073 -0.010554 0.659511 11.00000 0.02951 0.02353 = 0.01847 0.00026 0.00504 0.00636 AFIX 43 H5 2 0.436557 -0.068799 0.678792 11.00000 -1.20000 AFIX 0 C6 1 0.596893 0.713025 0.888745 11.00000 0.02741 0.02503 = 0.02049 0.00323 0.00601 0.01024 C7 1 0.170231 0.490829 0.891743 11.00000 0.02582 0.02873 = 0.02453 0.00023 0.00575 0.00569 AFIX 43 H7 2 0.068267 0.497587 0.908303 11.00000 -1.20000 AFIX 0 C8 1 0.835820 0.164376 0.602363 11.00000 0.02495 0.02673 = 0.02445 0.00275 0.00738 0.00858 AFIX 43 H8 2 0.936231 0.223258 0.583525 11.00000 -1.20000 AFIX 0 C9 1 0.317257 0.595998 0.899587 11.00000 0.02452 0.02213 = 0.01713 -0.00070 0.00266 0.00510 C10 1 0.474440 0.470008 0.841966 11.00000 0.03564 0.02636 = 0.01877 0.00355 0.00767 0.01510 AFIX 43 H10 2 0.576697 0.463832 0.825380 11.00000 -1.20000 AFIX 0 C11 1 0.768283 0.522740 0.450842 11.00000 0.03009 0.02145 = 0.02076 0.00516 0.00534 0.01004 AFIX 23 H11A 2 0.890329 0.550262 0.445665 11.00000 -1.20000 H11B 2 0.711417 0.563266 0.392517 11.00000 -1.20000 AFIX 0 C12 1 0.750520 0.563710 0.567876 11.00000 0.02555 0.02382 = 0.02283 0.00216 0.00436 0.01223 AFIX 13 H12 2 0.629373 0.555667 0.566110 11.00000 -1.20000 AFIX 0 C13 1 0.828027 0.043961 0.632135 11.00000 0.03001 0.02912 = 0.02595 0.00248 0.00402 0.01518 AFIX 43 H13 2 0.924862 0.019942 0.633239 11.00000 -1.20000 AFIX 0 C14 1 0.660019 0.315478 0.571965 11.00000 0.01977 0.02493 = 0.02249 0.00417 0.00746 0.00876 C15 1 0.348080 0.733007 0.930862 11.00000 0.02134 0.02358 = 0.02246 0.00053 0.00359 0.00791 C16 1 0.681102 -0.042129 0.660365 11.00000 0.03830 0.02290 = 0.01875 0.00328 0.00275 0.01235 AFIX 43 H16 2 0.679490 -0.123680 0.680503 11.00000 -1.20000 AFIX 0 C17 1 0.864586 0.698570 0.608189 11.00000 0.02861 0.02370 = 0.02572 0.00118 0.00387 0.00839 AFIX 137 H17A 2 0.850242 0.718778 0.684595 11.00000 -1.50000 H17B 2 0.833818 0.756794 0.556479 11.00000 -1.50000 H17C 2 0.983610 0.707525 0.609614 11.00000 -1.50000 AFIX 0 C18 1 0.129297 1.000271 0.880136 11.00000 0.02642 0.03009 = 0.03241 0.00403 0.00668 0.01081 AFIX 137 H18A 2 0.155355 1.030875 0.807155 11.00000 -1.50000 H18B 2 0.146140 1.072479 0.933146 11.00000 -1.50000 H18C 2 0.010637 0.942565 0.869380 11.00000 -1.50000 AFIX 0 C19 1 0.327928 0.363901 0.834688 11.00000 0.04641 0.02204 = 0.02175 0.00013 0.00707 0.01070 AFIX 43 H19 2 0.329469 0.282862 0.813209 11.00000 -1.20000 AFIX 0 C20 1 0.178804 0.374677 0.858444 11.00000 0.03419 0.02724 = 0.02496 0.00160 0.00599 0.00079 AFIX 43 H20 2 0.079959 0.300603 0.851741 11.00000 -1.20000 AFIX 0 C21 1 0.245847 0.930878 0.927409 11.00000 0.02969 0.02802 = 0.02780 0.00041 0.00480 0.01020 AFIX 13 H21 2 0.366722 0.989496 0.935689 11.00000 -1.20000 AFIX 0 C22 1 0.215890 0.879967 1.040949 11.00000 0.04124 0.03296 = 0.02564 0.00267 0.01092 0.01872 AFIX 23 H22A 2 0.092034 0.839084 1.038736 11.00000 -1.20000 H22B 2 0.261024 0.950879 1.100842 11.00000 -1.20000 AFIX 0 HKLF 4 REM p-1_a.res in P-1 REM wR2 = 0.099895, GooF = S = 1.11383, Restrained GooF = 1.11383 for all data REM R1 = 0.038087 for 3404 Fo > 4sig(Fo) and 0.060922 for all 4349 data REM 273 parameters refined using 0 restraints END WGHT 0.0254 1.5656 REM Highest difference peak 0.807, deepest hole -0.343, 1-sigma level 0.073 Q1 1 0.1325 0.8654 0.9419 11.00000 0.05 0.81 ; _shelx_res_checksum 56577 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 S1 S 0.80198(8) 0.45194(6) 0.66277(5) 0.02295(15) Uani 1 1 d . . . . . S2 S 0.67219(9) 0.35130(6) 0.42530(5) 0.02564(16) Uani 1 1 d . . . . . S3 S 0.21359(9) 0.79262(6) 0.83354(5) 0.02501(16) Uani 1 1 d . . . . . S4 S 0.32037(9) 0.76539(7) 1.07417(6) 0.02900(17) Uani 1 1 d . . . . . O1 O 0.5271(2) 0.79761(17) 0.92328(16) 0.0258(4) Uani 1 1 d . . . . . O2 O 0.2698(2) 0.12749(18) 0.63381(16) 0.0287(4) Uani 1 1 d . . . . . O3 O 0.4839(2) 0.28876(17) 0.58695(16) 0.0244(4) Uani 1 1 d . . . . . O4 O 0.7414(2) 0.74793(19) 0.87464(17) 0.0323(5) Uani 1 1 d . . . . . C1 C 0.6911(3) 0.1950(2) 0.6013(2) 0.0212(5) Uani 1 1 d . . . . . C2 C 0.4646(3) 0.5856(2) 0.8746(2) 0.0210(5) Uani 1 1 d . . . . . C3 C 0.5459(3) 0.1094(2) 0.6294(2) 0.0217(5) Uani 1 1 d . . . . . C4 C 0.4146(3) 0.1683(2) 0.6195(2) 0.0227(5) Uani 1 1 d . . . . . C5 C 0.5371(3) -0.0106(2) 0.6595(2) 0.0246(5) Uani 1 1 d . . . . . H5 H 0.436557 -0.068799 0.678792 0.029 Uiso 1 1 calc R U . . . C6 C 0.5969(3) 0.7130(2) 0.8887(2) 0.0238(5) Uani 1 1 d . . . . . C7 C 0.1702(3) 0.4908(3) 0.8917(2) 0.0273(6) Uani 1 1 d . . . . . H7 H 0.068267 0.497587 0.908303 0.033 Uiso 1 1 calc R U . . . C8 C 0.8358(3) 0.1644(3) 0.6024(2) 0.0252(6) Uani 1 1 d . . . . . H8 H 0.936231 0.223258 0.583525 0.030 Uiso 1 1 calc R U . . . C9 C 0.3173(3) 0.5960(2) 0.8996(2) 0.0223(5) Uani 1 1 d . . . . . C10 C 0.4744(4) 0.4700(2) 0.8420(2) 0.0255(6) Uani 1 1 d . . . . . H10 H 0.576697 0.463832 0.825380 0.031 Uiso 1 1 calc R U . . . C11 C 0.7683(3) 0.5227(2) 0.4508(2) 0.0237(5) Uani 1 1 d . . . . . H11A H 0.890329 0.550262 0.445665 0.028 Uiso 1 1 calc R U . . . H11B H 0.711417 0.563266 0.392517 0.028 Uiso 1 1 calc R U . . . C12 C 0.7505(3) 0.5637(2) 0.5679(2) 0.0231(5) Uani 1 1 d . . . . . H12 H 0.629373 0.555667 0.566110 0.028 Uiso 1 1 calc R U . . . C13 C 0.8280(4) 0.0440(3) 0.6321(2) 0.0272(6) Uani 1 1 d . . . . . H13 H 0.924862 0.019942 0.633239 0.033 Uiso 1 1 calc R U . . . C14 C 0.6600(3) 0.3155(2) 0.5720(2) 0.0217(5) Uani 1 1 d . . . . . C15 C 0.3481(3) 0.7330(2) 0.9309(2) 0.0225(5) Uani 1 1 d . . . . . C16 C 0.6811(4) -0.0421(3) 0.6604(2) 0.0265(6) Uani 1 1 d . . . . . H16 H 0.679490 -0.123680 0.680503 0.032 Uiso 1 1 calc R U . . . C17 C 0.8646(3) 0.6986(2) 0.6082(2) 0.0264(6) Uani 1 1 d . . . . . H17A H 0.850242 0.718778 0.684595 0.040 Uiso 1 1 calc R U . . . H17B H 0.833818 0.756794 0.556479 0.040 Uiso 1 1 calc R U . . . H17C H 0.983610 0.707525 0.609614 0.040 Uiso 1 1 calc R U . . . C18 C 0.1293(4) 1.0003(3) 0.8801(2) 0.0293(6) Uani 1 1 d . . . . . H18A H 0.155355 1.030875 0.807155 0.044 Uiso 1 1 calc R U . . . H18B H 0.146140 1.072479 0.933146 0.044 Uiso 1 1 calc R U . . . H18C H 0.010637 0.942565 0.869380 0.044 Uiso 1 1 calc R U . . . C19 C 0.3279(4) 0.3639(3) 0.8347(2) 0.0304(6) Uani 1 1 d . . . . . H19 H 0.329469 0.282862 0.813209 0.036 Uiso 1 1 calc R U . . . C20 C 0.1788(4) 0.3747(3) 0.8584(2) 0.0314(6) Uani 1 1 d . . . . . H20 H 0.079959 0.300603 0.851741 0.038 Uiso 1 1 calc R U . . . C21 C 0.2458(4) 0.9309(3) 0.9274(2) 0.0286(6) Uani 1 1 d . . . . . H21 H 0.366722 0.989496 0.935689 0.034 Uiso 1 1 calc R U . . . C22 C 0.2159(4) 0.8800(3) 1.0409(2) 0.0312(6) Uani 1 1 d . . . . . H22A H 0.092034 0.839084 1.038736 0.037 Uiso 1 1 calc R U . . . H22B H 0.261024 0.950879 1.100842 0.037 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0257(3) 0.0243(3) 0.0194(3) 0.0028(2) 0.0034(2) 0.0097(3) S2 0.0342(4) 0.0225(3) 0.0198(3) 0.0016(2) 0.0059(3) 0.0090(3) S3 0.0281(3) 0.0286(3) 0.0191(3) -0.0010(3) 0.0015(3) 0.0125(3) S4 0.0380(4) 0.0363(4) 0.0188(3) 0.0012(3) 0.0044(3) 0.0212(3) O1 0.0221(9) 0.0217(9) 0.0315(10) -0.0028(8) 0.0051(8) 0.0054(8) O2 0.0231(10) 0.0324(10) 0.0303(10) 0.0007(8) 0.0098(8) 0.0071(8) O3 0.0215(9) 0.0254(9) 0.0288(10) 0.0048(8) 0.0072(8) 0.0101(8) O4 0.0233(10) 0.0338(11) 0.0390(12) 0.0033(9) 0.0102(9) 0.0070(9) C1 0.0241(13) 0.0233(13) 0.0177(12) 0.0024(10) 0.0030(10) 0.0105(11) C2 0.0248(13) 0.0249(13) 0.0143(11) 0.0031(10) 0.0048(10) 0.0092(11) C3 0.0239(13) 0.0242(13) 0.0163(12) 0.0008(10) 0.0038(10) 0.0077(11) C4 0.0263(14) 0.0231(13) 0.0181(12) 0.0016(10) 0.0072(10) 0.0064(11) C5 0.0295(14) 0.0235(13) 0.0185(12) 0.0003(10) 0.0050(10) 0.0064(11) C6 0.0274(14) 0.0250(13) 0.0205(13) 0.0032(10) 0.0060(11) 0.0102(11) C7 0.0258(14) 0.0287(14) 0.0245(14) 0.0002(11) 0.0058(11) 0.0057(11) C8 0.0250(14) 0.0267(14) 0.0244(13) 0.0028(11) 0.0074(11) 0.0086(11) C9 0.0245(13) 0.0221(13) 0.0171(12) -0.0007(10) 0.0027(10) 0.0051(10) C10 0.0356(15) 0.0264(13) 0.0188(13) 0.0035(10) 0.0077(11) 0.0151(12) C11 0.0301(14) 0.0215(13) 0.0208(13) 0.0052(10) 0.0053(11) 0.0100(11) C12 0.0256(13) 0.0238(13) 0.0228(13) 0.0022(10) 0.0044(10) 0.0122(11) C13 0.0300(15) 0.0291(14) 0.0259(14) 0.0025(11) 0.0040(11) 0.0152(12) C14 0.0198(12) 0.0249(13) 0.0225(13) 0.0042(10) 0.0075(10) 0.0088(10) C15 0.0213(13) 0.0236(13) 0.0225(13) 0.0005(10) 0.0036(10) 0.0079(10) C16 0.0383(16) 0.0229(13) 0.0188(13) 0.0033(10) 0.0028(11) 0.0123(12) C17 0.0286(14) 0.0237(13) 0.0257(14) 0.0012(11) 0.0039(11) 0.0084(11) C18 0.0264(14) 0.0301(14) 0.0324(15) 0.0040(12) 0.0067(12) 0.0108(12) C19 0.0464(18) 0.0220(13) 0.0218(14) 0.0001(11) 0.0071(12) 0.0107(13) C20 0.0342(16) 0.0272(14) 0.0250(14) 0.0016(11) 0.0060(12) 0.0008(12) C21 0.0297(15) 0.0280(14) 0.0278(14) 0.0004(11) 0.0048(12) 0.0102(12) C22 0.0412(17) 0.0330(15) 0.0256(14) 0.0027(12) 0.0109(12) 0.0187(13) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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 C14 S1 C12 93.39(12) . . ? C11 S2 C14 97.51(12) . . ? C15 S3 C21 94.47(12) . . ? C22 S4 C15 97.32(12) . . ? C6 O1 C15 110.94(19) . . ? C4 O3 C14 111.12(19) . . ? C3 C1 C8 121.1(2) . . ? C3 C1 C14 109.2(2) . . ? C8 C1 C14 129.7(2) . . ? C9 C2 C6 108.5(2) . . ? C9 C2 C10 122.2(2) . . ? C10 C2 C6 129.2(2) . . ? C1 C3 C4 108.5(2) . . ? C1 C3 C5 122.0(2) . . ? C5 C3 C4 129.5(2) . . ? O2 C4 O3 121.2(2) . . ? O2 C4 C3 131.0(2) . . ? O3 C4 C3 107.8(2) . . ? C3 C5 H5 121.4 . . ? C3 C5 C16 117.2(2) . . ? C16 C5 H5 121.4 . . ? O1 C6 C2 107.8(2) . . ? O4 C6 O1 121.1(2) . . ? O4 C6 C2 131.1(2) . . ? C9 C7 H7 121.6 . . ? C9 C7 C20 116.8(3) . . ? C20 C7 H7 121.6 . . ? C1 C8 H8 121.3 . . ? C1 C8 C13 117.3(2) . . ? C13 C8 H8 121.3 . . ? C2 C9 C7 121.2(2) . . ? C2 C9 C15 109.1(2) . . ? C7 C9 C15 129.6(2) . . ? C2 C10 H10 121.6 . . ? C19 C10 C2 116.9(3) . . ? C19 C10 H10 121.6 . . ? S2 C11 H11A 109.7 . . ? S2 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C12 C11 S2 109.80(18) . . ? C12 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? S1 C12 H12 108.9 . . ? C11 C12 S1 105.98(17) . . ? C11 C12 H12 108.9 . . ? C17 C12 S1 110.96(18) . . ? C17 C12 C11 113.1(2) . . ? C17 C12 H12 108.9 . . ? C8 C13 H13 119.3 . . ? C8 C13 C16 121.3(3) . . ? C16 C13 H13 119.3 . . ? S1 C14 S2 108.08(13) . . ? O3 C14 S1 110.33(16) . . ? O3 C14 S2 108.25(16) . . ? O3 C14 C1 103.33(19) . . ? C1 C14 S1 113.19(18) . . ? C1 C14 S2 113.49(17) . . ? S3 C15 S4 108.17(13) . . ? O1 C15 S3 110.31(17) . . ? O1 C15 S4 108.62(16) . . ? O1 C15 C9 103.61(19) . . ? C9 C15 S3 111.61(18) . . ? C9 C15 S4 114.41(18) . . ? C5 C16 C13 121.0(3) . . ? C5 C16 H16 119.5 . . ? C13 C16 H16 119.5 . . ? C12 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? C12 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C18 H18A 109.5 . . ? C21 C18 H18B 109.5 . . ? C21 C18 H18C 109.5 . . ? C10 C19 H19 119.6 . . ? C10 C19 C20 120.8(3) . . ? C20 C19 H19 119.6 . . ? C7 C20 H20 119.0 . . ? C19 C20 C7 121.9(3) . . ? C19 C20 H20 119.0 . . ? S3 C21 H21 109.0 . . ? C18 C21 S3 110.9(2) . . ? C18 C21 H21 109.0 . . ? C18 C21 C22 113.5(2) . . ? C22 C21 S3 105.28(19) . . ? C22 C21 H21 109.0 . . ? S4 C22 H22A 109.6 . . ? S4 C22 H22B 109.6 . . ? C21 C22 S4 110.44(19) . . ? C21 C22 H22A 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? 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 S1 C12 1.825(3) . ? S1 C14 1.798(3) . ? S2 C11 1.817(3) . ? S2 C14 1.826(3) . ? S3 C15 1.796(3) . ? S3 C21 1.822(3) . ? S4 C15 1.825(3) . ? S4 C22 1.817(3) . ? O1 C6 1.376(3) . ? O1 C15 1.465(3) . ? O2 C4 1.202(3) . ? O3 C4 1.374(3) . ? O3 C14 1.467(3) . ? O4 C6 1.198(3) . ? C1 C3 1.380(4) . ? C1 C8 1.387(4) . ? C1 C14 1.505(3) . ? C2 C6 1.474(4) . ? C2 C9 1.381(4) . ? C2 C10 1.388(4) . ? C3 C4 1.473(4) . ? C3 C5 1.385(4) . ? C5 H5 0.9500 . ? C5 C16 1.388(4) . ? C7 H7 0.9500 . ? C7 C9 1.384(4) . ? C7 C20 1.392(4) . ? C8 H8 0.9500 . ? C8 C13 1.391(4) . ? C9 C15 1.504(3) . ? C10 H10 0.9500 . ? C10 C19 1.388(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.521(3) . ? C12 H12 1.0000 . ? C12 C17 1.512(4) . ? C13 H13 0.9500 . ? C13 C16 1.393(4) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C18 C21 1.508(4) . ? C19 H19 0.9500 . ? C19 C20 1.391(4) . ? C20 H20 0.9500 . ? C21 H21 1.0000 . ? C21 C22 1.516(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 S2 C11 C12 S1 43.4(2) . . . . ? S2 C11 C12 C17 165.15(18) . . . . ? S3 C21 C22 S4 44.0(2) . . . . ? C1 C3 C4 O2 178.5(3) . . . . ? C1 C3 C4 O3 -0.7(3) . . . . ? C1 C3 C5 C16 -0.1(4) . . . . ? C1 C8 C13 C16 -0.4(4) . . . . ? C2 C9 C15 S3 117.6(2) . . . . ? C2 C9 C15 S4 -119.2(2) . . . . ? C2 C9 C15 O1 -1.1(3) . . . . ? C2 C10 C19 C20 0.5(4) . . . . ? C3 C1 C8 C13 0.4(4) . . . . ? C3 C1 C14 S1 119.6(2) . . . . ? C3 C1 C14 S2 -116.8(2) . . . . ? C3 C1 C14 O3 0.2(3) . . . . ? C3 C5 C16 C13 0.1(4) . . . . ? C4 O3 C14 S1 -121.98(19) . . . . ? C4 O3 C14 S2 119.94(18) . . . . ? C4 O3 C14 C1 -0.7(3) . . . . ? C4 C3 C5 C16 179.1(2) . . . . ? C5 C3 C4 O2 -0.7(5) . . . . ? C5 C3 C4 O3 -179.9(2) . . . . ? C6 O1 C15 S3 -118.00(19) . . . . ? C6 O1 C15 S4 123.60(19) . . . . ? C6 O1 C15 C9 1.6(3) . . . . ? C6 C2 C9 C7 179.0(2) . . . . ? C6 C2 C9 C15 0.3(3) . . . . ? C6 C2 C10 C19 -179.5(3) . . . . ? C7 C9 C15 S3 -61.0(3) . . . . ? C7 C9 C15 S4 62.3(3) . . . . ? C7 C9 C15 O1 -179.6(3) . . . . ? C8 C1 C3 C4 -179.5(2) . . . . ? C8 C1 C3 C5 -0.2(4) . . . . ? C8 C1 C14 S1 -60.7(3) . . . . ? C8 C1 C14 S2 63.0(3) . . . . ? C8 C1 C14 O3 180.0(3) . . . . ? C8 C13 C16 C5 0.1(4) . . . . ? C9 C2 C6 O1 0.7(3) . . . . ? C9 C2 C6 O4 -178.8(3) . . . . ? C9 C2 C10 C19 0.4(4) . . . . ? C9 C7 C20 C19 0.4(4) . . . . ? C10 C2 C6 O1 -179.5(2) . . . . ? C10 C2 C6 O4 1.0(5) . . . . ? C10 C2 C9 C7 -0.9(4) . . . . ? C10 C2 C9 C15 -179.5(2) . . . . ? C10 C19 C20 C7 -0.9(4) . . . . ? C11 S2 C14 S1 -17.71(15) . . . . ? C11 S2 C14 O3 101.79(17) . . . . ? C11 S2 C14 C1 -144.12(19) . . . . ? C12 S1 C14 S2 38.37(14) . . . . ? C12 S1 C14 O3 -79.81(18) . . . . ? C12 S1 C14 C1 164.96(19) . . . . ? C14 S1 C12 C11 -49.92(19) . . . . ? C14 S1 C12 C17 -173.07(19) . . . . ? C14 S2 C11 C12 -15.9(2) . . . . ? C14 O3 C4 O2 -178.4(2) . . . . ? C14 O3 C4 C3 0.9(3) . . . . ? C14 C1 C3 C4 0.3(3) . . . . ? C14 C1 C3 C5 179.6(2) . . . . ? C14 C1 C8 C13 -179.3(3) . . . . ? C15 S3 C21 C18 -172.1(2) . . . . ? C15 S3 C21 C22 -48.9(2) . . . . ? C15 S4 C22 C21 -18.0(2) . . . . ? C15 O1 C6 O4 178.1(2) . . . . ? C15 O1 C6 C2 -1.4(3) . . . . ? C18 C21 C22 S4 165.5(2) . . . . ? C20 C7 C9 C2 0.5(4) . . . . ? C20 C7 C9 C15 178.8(3) . . . . ? C21 S3 C15 S4 36.42(15) . . . . ? C21 S3 C15 O1 -82.25(18) . . . . ? C21 S3 C15 C9 163.14(19) . . . . ? C22 S4 C15 S3 -15.20(16) . . . . ? C22 S4 C15 O1 104.54(18) . . . . ? C22 S4 C15 C9 -140.3(2) . . . . ?