#------------------------------------------------------------------------------ #$Date: 2024-06-22 01:17:30 +0300 (Sat, 22 Jun 2024) $ #$Revision: 292521 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/19/1571962.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_1571962 loop_ _publ_author_name 'Lai, Jingxiong' 'Cai, Wei' 'Huang, You' _publ_section_title ; Enantioselective Phosphine-Catalyzed [6+1] Annulations of \a-Allyl Allenoates with 1,1-Bisnucleophiles ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02487G _journal_year 2024 _chemical_formula_moiety 'C21 H25 N O6 S' _chemical_formula_sum 'C21 H25 N O6 S' _chemical_formula_weight 419.48 _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 2022-10-08 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) ; _audit_update_record ; 2022-10-08 deposited with the CCDC. 2024-06-20 downloaded from the CCDC. ; _cell_angle_alpha 93.270(4) _cell_angle_beta 99.190(4) _cell_angle_gamma 90.759(4) _cell_formula_units_Z 2 _cell_length_a 7.0682(6) _cell_length_b 8.2714(7) _cell_length_c 18.0737(16) _cell_measurement_reflns_used 8847 _cell_measurement_temperature 193.00 _cell_measurement_theta_max 60.48 _cell_measurement_theta_min 2.16 _cell_volume 1041.13(16) _computing_cell_refinement 'SAINT V8.40B (Bruker, 2019)' _computing_data_collection 'APEX4 V2022.1-1 (Bruker, 2022)' _computing_data_reduction 'SAINT V8.40B (Bruker, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/2 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 193.00 _diffrn_detector CPAD _diffrn_detector_area_resol_mean 7.41 _diffrn_detector_type 'Bruker PHOTON II' _diffrn_measured_fraction_theta_full 0.977 _diffrn_measured_fraction_theta_max 0.948 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Bruker D8 VENTURE Metaljet PHOTON II' _diffrn_measurement_method '\w and \f shutterless scans' _diffrn_measurement_specimen_support 'nylon loop' _diffrn_radiation_monochromator 'Helios Multi-layer Optic' _diffrn_radiation_probe x-ray _diffrn_radiation_type GaK\a _diffrn_radiation_wavelength 1.34139 _diffrn_reflns_av_R_equivalents 0.0455 _diffrn_reflns_av_unetI/netI 0.0459 _diffrn_reflns_Laue_measured_fraction_full 0.977 _diffrn_reflns_Laue_measured_fraction_max 0.948 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 11621 _diffrn_reflns_point_group_measured_fraction_full 0.977 _diffrn_reflns_point_group_measured_fraction_max 0.948 _diffrn_reflns_theta_full 53.594 _diffrn_reflns_theta_max 60.699 _diffrn_reflns_theta_min 4.320 _diffrn_source MetalJet _diffrn_source_current 2.85 _diffrn_source_power 0.1986735 _diffrn_source_type 'Liquid Metal source' _diffrn_source_voltage 69.71 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 1.110 _exptl_absorpt_correction_T_max 0.7518 _exptl_absorpt_correction_T_min 0.5302 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1269 before and 0.0794 after correction. The Ratio of minimum to maximum transmission is 0.7052. The \l/2 correction factor is Not present. ; _exptl_crystal_density_diffrn 1.338 _exptl_crystal_description block _exptl_crystal_F_000 444 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.797 _refine_diff_density_min -0.681 _refine_diff_density_rms 0.067 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 265 _refine_ls_number_reflns 4539 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0709 _refine_ls_R_factor_gt 0.0627 _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^)+(0.0512P)^2^+1.4839P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1597 _refine_ls_wR_factor_ref 0.1655 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3901 _reflns_number_total 4539 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02487g2.cif _cod_data_source_block 220929_wqangz_262959_0m _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas ; _cod_database_code 1571962 _shelx_shelxl_version_number 2019/2 _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 0.897 _shelx_estimated_absorpt_t_min 0.869 _olex2_refinement_description ; 1.a Ternary CH refined with riding coordinates: C14(H14) 1.b Secondary CH2 refined with riding coordinates: C15(H15A,H15B), C10(H10A,H10B), C13(H13A,H13B), C17(H17A,H17B), C20(H20A,H20B) 1.c Aromatic/amide H refined with riding coordinates: C11(H11), C6(H6), C4(H4), C7(H7), C3(H3) 1.d Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C21(H21A,H21B,H21C), C18(H18A,H18B,H18C) ; _shelx_res_file ; TITL 220929_wqangz_262959_0m_a.res in P-1 220929_wqangz_262959_0m.res created by SHELXL-2019/2 at 21:16:39 on 30-Sep-2022 REM Old TITL 220929_WQANGZ_262959_0m in P-1 REM SHELXT solution in P-1: R1 0.148, Rweak 0.010, Alpha 0.054 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C21 N O6 S CELL 1.34139 7.0682 8.2714 18.0737 93.27 99.19 90.759 ZERR 2 0.0006 0.0007 0.0016 0.004 0.004 0.004 LATT 1 SFAC C H N O S DISP C 0.0137 0.0067 57.1 DISP H 0 0 0.6 DISP N 0.0241 0.0134 109.9 DISP O 0.0389 0.0241 193.4 DISP S 0.2925 0.4295 3294.4 UNIT 42 50 2 12 2 L.S. 10 PLAN 2 SIZE 0.1 0.12 0.13 TEMP -80.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta SIZE 0.1 0.12 0.13 TEMP -80.15 OMIT -1 4 1 REM REM REM WGHT 0.051200 1.483900 FVAR 1.19171 S1 5 0.747174 0.320150 0.103682 11.00000 0.04480 0.02476 = 0.03141 -0.00030 0.00602 -0.00619 O4 4 0.336371 -0.077341 0.308158 11.00000 0.04635 0.02488 = 0.05615 -0.00061 0.02226 -0.00627 O6 4 0.735729 0.560826 0.463898 11.00000 0.05921 0.03811 = 0.03522 -0.00895 0.00729 -0.00463 O2 4 0.551610 0.343319 0.071804 11.00000 0.04463 0.04440 = 0.04217 0.00537 -0.00621 -0.01528 O1 4 0.847124 0.182051 0.079042 11.00000 0.07953 0.02577 = 0.04219 -0.00255 0.02388 -0.00155 O3 4 0.584672 -0.177064 0.259372 11.00000 0.05379 0.02326 = 0.09588 0.00734 0.03474 0.00447 O5 4 0.742322 0.307835 0.500752 11.00000 0.07490 0.04877 = 0.03290 0.00436 0.00564 -0.00217 N1 3 1.106397 0.318272 0.267904 11.00000 0.03839 0.05251 = 0.04946 0.00540 0.00578 0.00346 C9 1 0.948195 0.310021 0.241316 11.00000 0.03662 0.02467 = 0.03733 0.00155 0.00879 0.00196 C8 1 0.746998 0.300020 0.205115 11.00000 0.03137 0.02006 = 0.03342 0.00023 0.00616 -0.00153 C15 1 0.658378 0.129455 0.210158 11.00000 0.04281 0.02250 = 0.03723 -0.00138 0.00898 -0.00611 AFIX 23 H15A 2 0.565059 0.102964 0.163942 11.00000 -1.20000 H15B 2 0.761337 0.049095 0.212016 11.00000 -1.20000 AFIX 0 C5 1 0.883562 0.495885 0.097297 11.00000 0.03877 0.02524 = 0.03050 0.00132 0.00611 -0.00424 C10 1 0.632604 0.438789 0.235496 11.00000 0.03406 0.02209 = 0.03931 0.00228 0.00628 0.00076 AFIX 23 H10A 2 0.669635 0.540969 0.215047 11.00000 -1.20000 H10B 2 0.494520 0.417857 0.216825 11.00000 -1.20000 AFIX 0 C16 1 0.497761 -0.063953 0.280223 11.00000 0.03511 0.02396 = 0.03953 0.00252 0.00826 -0.00282 C11 1 0.661601 0.461057 0.319451 11.00000 0.03039 0.02421 = 0.03841 -0.00362 0.00829 -0.00053 AFIX 43 H11 2 0.661399 0.569797 0.339428 11.00000 -1.20000 AFIX 0 C6 1 0.792267 0.643051 0.088825 11.00000 0.03650 0.03102 = 0.04223 0.00497 0.00774 -0.00015 AFIX 43 H6 2 0.656672 0.647981 0.083971 11.00000 -1.20000 AFIX 0 C19 1 0.724565 0.400180 0.451462 11.00000 0.03099 0.03862 = 0.03965 -0.00256 0.00828 -0.00392 C14 1 0.557194 0.112955 0.278183 11.00000 0.03266 0.02278 = 0.03753 0.00233 0.00627 -0.00238 AFIX 13 H14 2 0.439106 0.179309 0.271473 11.00000 -1.20000 AFIX 0 C13 1 0.680109 0.166775 0.353582 11.00000 0.04308 0.02533 = 0.03529 0.00113 0.00617 -0.00067 AFIX 23 H13A 2 0.627982 0.114848 0.394294 11.00000 -1.20000 H13B 2 0.812180 0.128297 0.353686 11.00000 -1.20000 AFIX 0 C4 1 1.080005 0.485593 0.101254 11.00000 0.03874 0.03565 = 0.04178 0.00876 0.01146 0.00446 AFIX 43 H4 2 1.140650 0.383897 0.104898 11.00000 -1.20000 AFIX 0 C12 1 0.687697 0.348218 0.369917 11.00000 0.02927 0.02978 = 0.03610 -0.00202 0.00785 -0.00107 C7 1 0.902402 0.782520 0.087577 11.00000 0.04888 0.02547 = 0.04333 0.00347 0.01101 -0.00018 AFIX 43 H7 2 0.841300 0.883770 0.082306 11.00000 -1.20000 AFIX 0 C2 1 1.100163 0.776672 0.093894 11.00000 0.04463 0.03758 = 0.03169 0.00169 0.00444 -0.01242 C17 1 0.266860 -0.240883 0.317402 11.00000 0.04567 0.02709 = 0.05185 0.00481 0.01384 -0.00768 AFIX 23 H17A 2 0.340624 -0.285183 0.362729 11.00000 -1.20000 H17B 2 0.281783 -0.313183 0.273234 11.00000 -1.20000 AFIX 0 C3 1 1.186276 0.626816 0.099787 11.00000 0.03625 0.04605 = 0.04371 0.00956 0.00618 -0.00348 AFIX 43 H3 2 1.321446 0.621190 0.102885 11.00000 -1.20000 AFIX 0 C20 1 0.771099 0.623884 0.541339 11.00000 0.04329 0.05240 = 0.03548 -0.01312 0.00651 -0.00320 AFIX 23 H20A 2 0.895543 0.586272 0.567091 11.00000 -1.20000 H20B 2 0.668549 0.586935 0.568296 11.00000 -1.20000 AFIX 0 C1 1 1.218839 0.928926 0.094604 11.00000 0.06054 0.04523 = 0.04675 0.00091 0.00350 -0.02486 AFIX 137 H1A 2 1.160351 0.995747 0.054396 11.00000 -1.50000 H1B 2 1.348701 0.900865 0.086715 11.00000 -1.50000 H1C 2 1.224888 0.989497 0.143164 11.00000 -1.50000 AFIX 0 C21 1 0.773741 0.803976 0.539757 11.00000 0.07253 0.05261 = 0.05215 -0.02181 0.01122 -0.00616 AFIX 137 H21A 2 0.653470 0.838785 0.510844 11.00000 -1.50000 H21B 2 0.881674 0.839240 0.516199 11.00000 -1.50000 H21C 2 0.787816 0.852238 0.591188 11.00000 -1.50000 AFIX 0 C18 1 0.060336 -0.229721 0.325072 11.00000 0.04345 0.04359 = 0.08167 0.01171 0.01342 -0.00818 AFIX 137 H18A 2 -0.010055 -0.181121 0.280943 11.00000 -1.50000 H18B 2 0.047976 -0.162263 0.370340 11.00000 -1.50000 H18C 2 0.007413 -0.338447 0.328972 11.00000 -1.50000 AFIX 0 HKLF 4 REM 220929_wqangz_262959_0m_a.res in P-1 REM wR2 = 0.1655, GooF = S = 1.080, Restrained GooF = 1.080 for all data REM R1 = 0.0627 for 3901 Fo > 4sig(Fo) and 0.0709 for all 4539 data REM 265 parameters refined using 0 restraints END WGHT 0.0486 1.4883 REM Highest difference peak 0.797, deepest hole -0.681, 1-sigma level 0.067 Q1 1 0.7607 0.3174 0.1576 11.00000 0.05 0.80 Q2 1 0.7125 0.3146 0.0492 11.00000 0.05 0.55 ; _shelx_res_checksum 7005 _olex2_submission_special_instructions 'No special instructions were received' _site XU 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 0.74717(10) 0.32015(7) 0.10368(3) 0.03380(18) Uani 1 1 d . . . . . O4 O 0.3364(3) -0.0773(2) 0.30816(12) 0.0411(5) Uani 1 1 d . . . . . O6 O 0.7357(3) 0.5608(2) 0.46390(11) 0.0447(5) Uani 1 1 d . . . . . O2 O 0.5516(3) 0.3433(3) 0.07180(12) 0.0452(5) Uani 1 1 d . . . . . O1 O 0.8471(4) 0.1821(2) 0.07904(12) 0.0478(5) Uani 1 1 d . . . . . O3 O 0.5847(3) -0.1771(2) 0.25937(15) 0.0550(6) Uani 1 1 d . . . . . O5 O 0.7423(4) 0.3078(3) 0.50075(12) 0.0525(6) Uani 1 1 d . . . . . N1 N 1.1064(4) 0.3183(3) 0.26790(15) 0.0468(6) Uani 1 1 d . . . . . C9 C 0.9482(4) 0.3100(3) 0.24132(15) 0.0326(5) Uani 1 1 d . . . . . C8 C 0.7470(4) 0.3000(3) 0.20512(14) 0.0282(5) Uani 1 1 d . . . . . C15 C 0.6584(4) 0.1295(3) 0.21016(15) 0.0341(6) Uani 1 1 d . . . . . H15A H 0.565059 0.102964 0.163942 0.041 Uiso 1 1 calc R U . . . H15B H 0.761337 0.049095 0.212016 0.041 Uiso 1 1 calc R U . . . C5 C 0.8836(4) 0.4959(3) 0.09730(14) 0.0315(5) Uani 1 1 d . . . . . C10 C 0.6326(4) 0.4388(3) 0.23550(15) 0.0318(5) Uani 1 1 d . . . . . H10A H 0.669635 0.540969 0.215047 0.038 Uiso 1 1 calc R U . . . H10B H 0.494520 0.417857 0.216825 0.038 Uiso 1 1 calc R U . . . C16 C 0.4978(4) -0.0640(3) 0.28022(15) 0.0326(5) Uani 1 1 d . . . . . C11 C 0.6616(4) 0.4611(3) 0.31945(15) 0.0309(5) Uani 1 1 d . . . . . H11 H 0.661399 0.569797 0.339428 0.037 Uiso 1 1 calc R U . . . C6 C 0.7923(4) 0.6431(3) 0.08883(16) 0.0363(6) Uani 1 1 d . . . . . H6 H 0.656672 0.647981 0.083971 0.044 Uiso 1 1 calc R U . . . C19 C 0.7246(4) 0.4002(3) 0.45146(16) 0.0364(6) Uani 1 1 d . . . . . C14 C 0.5572(4) 0.1130(3) 0.27818(15) 0.0309(5) Uani 1 1 d . . . . . H14 H 0.439106 0.179309 0.271473 0.037 Uiso 1 1 calc R U . . . C13 C 0.6801(4) 0.1668(3) 0.35358(15) 0.0346(6) Uani 1 1 d . . . . . H13A H 0.627982 0.114848 0.394294 0.042 Uiso 1 1 calc R U . . . H13B H 0.812180 0.128297 0.353686 0.042 Uiso 1 1 calc R U . . . C4 C 1.0800(4) 0.4856(3) 0.10125(16) 0.0379(6) Uani 1 1 d . . . . . H4 H 1.140650 0.383897 0.104898 0.045 Uiso 1 1 calc R U . . . C12 C 0.6877(4) 0.3482(3) 0.36992(15) 0.0316(5) Uani 1 1 d . . . . . C7 C 0.9024(4) 0.7825(3) 0.08758(16) 0.0388(6) Uani 1 1 d . . . . . H7 H 0.841300 0.883770 0.082306 0.047 Uiso 1 1 calc R U . . . C2 C 1.1002(4) 0.7767(3) 0.09389(15) 0.0383(6) Uani 1 1 d . . . . . C17 C 0.2669(4) -0.2409(3) 0.31740(18) 0.0409(6) Uani 1 1 d . . . . . H17A H 0.340624 -0.285183 0.362729 0.049 Uiso 1 1 calc R U . . . H17B H 0.281783 -0.313183 0.273234 0.049 Uiso 1 1 calc R U . . . C3 C 1.1863(4) 0.6268(4) 0.09979(17) 0.0418(6) Uani 1 1 d . . . . . H3 H 1.321446 0.621190 0.102885 0.050 Uiso 1 1 calc R U . . . C20 C 0.7711(4) 0.6239(4) 0.54134(16) 0.0444(7) Uani 1 1 d . . . . . H20A H 0.895543 0.586272 0.567091 0.053 Uiso 1 1 calc R U . . . H20B H 0.668549 0.586935 0.568296 0.053 Uiso 1 1 calc R U . . . C1 C 1.2188(5) 0.9289(4) 0.09460(19) 0.0517(8) Uani 1 1 d . . . . . H1A H 1.160351 0.995747 0.054396 0.078 Uiso 1 1 calc R U . . . H1B H 1.348701 0.900865 0.086715 0.078 Uiso 1 1 calc R U . . . H1C H 1.224888 0.989497 0.143164 0.078 Uiso 1 1 calc R U . . . C21 C 0.7737(6) 0.8040(4) 0.5398(2) 0.0600(9) Uani 1 1 d . . . . . H21A H 0.653470 0.838785 0.510844 0.090 Uiso 1 1 calc R U . . . H21B H 0.881674 0.839240 0.516199 0.090 Uiso 1 1 calc R U . . . H21C H 0.787816 0.852238 0.591188 0.090 Uiso 1 1 calc R U . . . C18 C 0.0603(5) -0.2297(4) 0.3251(2) 0.0556(9) Uani 1 1 d . . . . . H18A H -0.010055 -0.181121 0.280943 0.083 Uiso 1 1 calc R U . . . H18B H 0.047976 -0.162263 0.370340 0.083 Uiso 1 1 calc R U . . . H18C H 0.007413 -0.338447 0.328972 0.083 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 0.0448(4) 0.0248(3) 0.0314(3) -0.0003(2) 0.0060(3) -0.0062(2) O4 0.0464(11) 0.0249(9) 0.0562(12) -0.0006(8) 0.0223(9) -0.0063(8) O6 0.0592(13) 0.0381(11) 0.0352(11) -0.0089(8) 0.0073(9) -0.0046(9) O2 0.0446(11) 0.0444(12) 0.0422(11) 0.0054(9) -0.0062(9) -0.0153(9) O1 0.0795(16) 0.0258(10) 0.0422(11) -0.0026(8) 0.0239(11) -0.0016(9) O3 0.0538(13) 0.0233(10) 0.0959(19) 0.0073(10) 0.0347(13) 0.0045(9) O5 0.0749(16) 0.0488(13) 0.0329(11) 0.0044(9) 0.0056(10) -0.0022(11) N1 0.0384(14) 0.0525(16) 0.0495(15) 0.0054(12) 0.0058(11) 0.0035(11) C9 0.0366(14) 0.0247(12) 0.0373(13) 0.0016(10) 0.0088(11) 0.0020(10) C8 0.0314(12) 0.0201(11) 0.0334(12) 0.0002(9) 0.0062(10) -0.0015(9) C15 0.0428(14) 0.0225(11) 0.0372(14) -0.0014(10) 0.0090(11) -0.0061(10) C5 0.0388(13) 0.0252(12) 0.0305(12) 0.0013(9) 0.0061(10) -0.0042(10) C10 0.0341(13) 0.0221(11) 0.0393(14) 0.0023(9) 0.0063(10) 0.0008(9) C16 0.0351(13) 0.0240(12) 0.0395(14) 0.0025(10) 0.0083(10) -0.0028(10) C11 0.0304(12) 0.0242(11) 0.0384(13) -0.0036(10) 0.0083(10) -0.0005(9) C6 0.0365(14) 0.0310(13) 0.0422(15) 0.0050(11) 0.0077(11) -0.0002(10) C19 0.0310(13) 0.0386(14) 0.0396(15) -0.0026(11) 0.0083(11) -0.0039(10) C14 0.0327(12) 0.0228(11) 0.0375(13) 0.0023(9) 0.0063(10) -0.0024(9) C13 0.0431(14) 0.0253(12) 0.0353(13) 0.0011(10) 0.0062(11) -0.0007(10) C4 0.0387(14) 0.0357(14) 0.0418(15) 0.0088(11) 0.0115(11) 0.0045(11) C12 0.0293(12) 0.0298(12) 0.0361(13) -0.0020(10) 0.0079(10) -0.0011(9) C7 0.0489(16) 0.0255(12) 0.0433(15) 0.0035(11) 0.0110(12) -0.0002(11) C2 0.0446(15) 0.0376(14) 0.0317(13) 0.0017(11) 0.0044(11) -0.0124(12) C17 0.0457(16) 0.0271(13) 0.0519(17) 0.0048(11) 0.0138(13) -0.0077(11) C3 0.0362(14) 0.0461(16) 0.0437(16) 0.0096(12) 0.0062(12) -0.0035(12) C20 0.0433(16) 0.0524(18) 0.0355(15) -0.0131(12) 0.0065(12) -0.0032(13) C1 0.061(2) 0.0452(17) 0.0467(17) 0.0009(13) 0.0035(14) -0.0249(15) C21 0.073(2) 0.053(2) 0.052(2) -0.0218(16) 0.0112(17) -0.0062(17) C18 0.0435(17) 0.0436(18) 0.082(3) 0.0117(16) 0.0134(16) -0.0082(14) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0137 0.0067 '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' N N 0.0241 0.0134 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0389 0.0241 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.2925 0.4295 '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 O2 S1 O1 120.00(14) . . ? O2 S1 C8 105.57(12) . . ? O2 S1 C5 109.85(13) . . ? O1 S1 C8 105.65(12) . . ? O1 S1 C5 108.89(13) . . ? C5 S1 C8 105.89(11) . . ? C16 O4 C17 117.2(2) . . ? C19 O6 C20 117.2(2) . . ? N1 C9 C8 178.4(3) . . ? C9 C8 S1 106.45(17) . . ? C9 C8 C15 111.3(2) . . ? C9 C8 C10 110.8(2) . . ? C15 C8 S1 104.82(16) . . ? C10 C8 S1 109.21(17) . . ? C10 C8 C15 113.8(2) . . ? C8 C15 H15A 108.7 . . ? C8 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? C14 C15 C8 114.2(2) . . ? C14 C15 H15A 108.7 . . ? C14 C15 H15B 108.7 . . ? C6 C5 S1 119.3(2) . . ? C4 C5 S1 119.4(2) . . ? C4 C5 C6 121.3(2) . . ? C8 C10 H10A 108.7 . . ? C8 C10 H10B 108.7 . . ? H10A C10 H10B 107.6 . . ? C11 C10 C8 114.3(2) . . ? C11 C10 H10A 108.7 . . ? C11 C10 H10B 108.7 . . ? O4 C16 C14 110.9(2) . . ? O3 C16 O4 124.2(2) . . ? O3 C16 C14 124.9(2) . . ? C10 C11 H11 115.7 . . ? C12 C11 C10 128.6(2) . . ? C12 C11 H11 115.7 . . ? C5 C6 H6 120.6 . . ? C7 C6 C5 118.9(3) . . ? C7 C6 H6 120.6 . . ? O6 C19 C12 112.8(2) . . ? O5 C19 O6 123.4(3) . . ? O5 C19 C12 123.8(3) . . ? C15 C14 H14 108.6 . . ? C15 C14 C13 114.3(2) . . ? C16 C14 C15 108.0(2) . . ? C16 C14 H14 108.6 . . ? C16 C14 C13 108.7(2) . . ? C13 C14 H14 108.6 . . ? C14 C13 H13A 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C12 C13 C14 113.5(2) . . ? C12 C13 H13A 108.9 . . ? C12 C13 H13B 108.9 . . ? C5 C4 H4 120.8 . . ? C5 C4 C3 118.5(3) . . ? C3 C4 H4 120.8 . . ? C11 C12 C19 119.0(2) . . ? C11 C12 C13 126.6(2) . . ? C19 C12 C13 114.4(2) . . ? C6 C7 H7 119.5 . . ? C2 C7 C6 121.1(3) . . ? C2 C7 H7 119.5 . . ? C7 C2 C3 118.5(3) . . ? C7 C2 C1 120.7(3) . . ? C3 C2 C1 120.7(3) . . ? O4 C17 H17A 110.2 . . ? O4 C17 H17B 110.2 . . ? O4 C17 C18 107.3(2) . . ? H17A C17 H17B 108.5 . . ? C18 C17 H17A 110.2 . . ? C18 C17 H17B 110.2 . . ? C4 C3 C2 121.7(3) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? O6 C20 H20A 110.4 . . ? O6 C20 H20B 110.4 . . ? O6 C20 C21 106.6(3) . . ? H20A C20 H20B 108.6 . . ? C21 C20 H20A 110.4 . . ? C21 C20 H20B 110.4 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1B 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21B 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 S1 O2 1.430(2) . ? S1 O1 1.437(2) . ? S1 C8 1.850(3) . ? S1 C5 1.753(3) . ? O4 C16 1.325(3) . ? O4 C17 1.461(3) . ? O6 C19 1.334(3) . ? O6 C20 1.447(3) . ? O3 C16 1.202(3) . ? O5 C19 1.199(4) . ? N1 C9 1.144(4) . ? C9 C8 1.467(4) . ? C8 C15 1.549(3) . ? C8 C10 1.539(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C15 C14 1.529(4) . ? C5 C6 1.390(4) . ? C5 C4 1.383(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C11 1.499(4) . ? C16 C14 1.521(3) . ? C11 H11 0.9500 . ? C11 C12 1.336(4) . ? C6 H6 0.9500 . ? C6 C7 1.386(4) . ? C19 C12 1.492(4) . ? C14 H14 1.0000 . ? C14 C13 1.534(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C13 C12 1.512(3) . ? C4 H4 0.9500 . ? C4 C3 1.384(4) . ? C7 H7 0.9500 . ? C7 C2 1.386(4) . ? C2 C3 1.390(4) . ? C2 C1 1.502(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C17 C18 1.492(4) . ? C3 H3 0.9500 . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C20 C21 1.491(5) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? 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 S1 C8 C15 C14 -152.56(19) . . . . ? S1 C8 C10 C11 -165.56(17) . . . . ? S1 C5 C6 C7 176.8(2) . . . . ? S1 C5 C4 C3 -176.9(2) . . . . ? O4 C16 C14 C15 -147.5(2) . . . . ? O4 C16 C14 C13 88.0(3) . . . . ? O6 C19 C12 C11 -3.0(3) . . . . ? O6 C19 C12 C13 178.2(2) . . . . ? O2 S1 C8 C9 -168.53(16) . . . . ? O2 S1 C8 C15 73.50(19) . . . . ? O2 S1 C8 C10 -48.84(19) . . . . ? O2 S1 C5 C6 21.5(3) . . . . ? O2 S1 C5 C4 -158.9(2) . . . . ? O1 S1 C8 C9 63.37(19) . . . . ? O1 S1 C8 C15 -54.6(2) . . . . ? O1 S1 C8 C10 -176.94(17) . . . . ? O1 S1 C5 C6 154.7(2) . . . . ? O1 S1 C5 C4 -25.7(3) . . . . ? O3 C16 C14 C15 32.5(4) . . . . ? O3 C16 C14 C13 -92.0(3) . . . . ? O5 C19 C12 C11 177.0(3) . . . . ? O5 C19 C12 C13 -1.8(4) . . . . ? C9 C8 C15 C14 92.8(3) . . . . ? C9 C8 C10 C11 -48.6(3) . . . . ? C8 S1 C5 C6 -92.1(2) . . . . ? C8 S1 C5 C4 87.5(2) . . . . ? C8 C15 C14 C16 -173.8(2) . . . . ? C8 C15 C14 C13 -52.7(3) . . . . ? C8 C10 C11 C12 -35.6(4) . . . . ? C15 C8 C10 C11 77.7(3) . . . . ? C15 C14 C13 C12 80.4(3) . . . . ? C5 S1 C8 C9 -52.05(19) . . . . ? C5 S1 C8 C15 -170.03(17) . . . . ? C5 S1 C8 C10 67.64(19) . . . . ? C5 C6 C7 C2 0.6(4) . . . . ? C5 C4 C3 C2 -0.5(4) . . . . ? C10 C8 C15 C14 -33.3(3) . . . . ? C10 C11 C12 C19 176.7(2) . . . . ? C10 C11 C12 C13 -4.7(4) . . . . ? C16 O4 C17 C18 -162.0(3) . . . . ? C16 C14 C13 C12 -158.9(2) . . . . ? C6 C5 C4 C3 2.7(4) . . . . ? C6 C7 C2 C3 1.5(4) . . . . ? C6 C7 C2 C1 -178.3(3) . . . . ? C19 O6 C20 C21 -179.1(3) . . . . ? C14 C13 C12 C11 -25.2(4) . . . . ? C14 C13 C12 C19 153.5(2) . . . . ? C4 C5 C6 C7 -2.8(4) . . . . ? C7 C2 C3 C4 -1.6(4) . . . . ? C17 O4 C16 O3 3.3(4) . . . . ? C17 O4 C16 C14 -176.8(2) . . . . ? C20 O6 C19 O5 0.0(4) . . . . ? C20 O6 C19 C12 180.0(2) . . . . ? C1 C2 C3 C4 178.3(3) . . . . ?