#------------------------------------------------------------------------------ #$Date: 2020-05-13 02:19:32 +0300 (Wed, 13 May 2020) $ #$Revision: 251997 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038352.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_4038352 loop_ _publ_author_name 'Ruggeri, Michele' 'Dombrowski, Amanda W.' 'Djuric, Stevan W.' 'Baxendale, Ian R.' _publ_section_title ; A rearrangement of 3-hydroxyazetidines into 2-oxazolines. ; _journal_name_full 'The Journal of organic chemistry' _journal_paper_doi 10.1021/acs.joc.0c00656 _journal_year 2020 _chemical_formula_moiety 'C24 H25 N O3 S2' _chemical_formula_sum 'C24 H25 N O3 S2' _chemical_formula_weight 439.57 _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 2019-11-28 _audit_creation_method ; Olex2 1.3-alpha (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _cell_angle_alpha 69.0014(14) _cell_angle_beta 87.1419(16) _cell_angle_gamma 87.6311(16) _cell_formula_units_Z 4 _cell_length_a 5.9971(2) _cell_length_b 19.0997(8) _cell_length_c 20.3305(8) _cell_measurement_reflns_used 9942 _cell_measurement_temperature 273.15 _cell_measurement_theta_max 29.69 _cell_measurement_theta_min 2.29 _cell_volume 2170.67(15) _computing_cell_refinement 'SAINT v8.38A (Bruker, 2017)' _computing_data_collection 'APEX3 v.2016.1-0 (Bruker, 2016)' _computing_data_reduction 'SAINT v8.38A (Bruker, 2017)' _computing_molecular_graphics 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3-alpha (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015a)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 120 _diffrn_detector 'Bruker PHOTON 100 CMOS' _diffrn_detector_area_resol_mean 10.4 _diffrn_detector_type 'CMOS sensor' _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device '3-circle area detector diffractometer' _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0425 _diffrn_reflns_av_unetI/netI 0.0437 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 45131 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.699 _diffrn_reflns_theta_min 2.041 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_type 'Incoatec I\mS microsource' _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9480 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker, 2016) was used for absorption correction. wR2(int) was 0.1478 before and 0.0452 after correction. The Ratio of minimum to maximum transmission is 0.9480. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.345 _exptl_crystal_description lathe _exptl_crystal_F_000 928 _exptl_crystal_size_max 0.436 _exptl_crystal_size_mid 0.099 _exptl_crystal_size_min 0.064 _refine_diff_density_max 0.408 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.054 _refine_ls_extinction_coef 0.0022(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick, 2015a)' _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 554 _refine_ls_number_reflns 11184 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0621 _refine_ls_R_factor_gt 0.0386 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0496P)^2^+0.4806P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0934 _refine_ls_wR_factor_ref 0.1009 _reflns_Friedel_coverage 0.000 _reflns_number_gt 8342 _reflns_number_total 11184 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 19srv351.cif _cod_data_source_block 19srv351 _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/ACS/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 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 4038352 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Others Uiso(H10A)=Uiso(H10B)=Uiso(H10C)=FVAR(1) Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=FVAR(2) Uiso(H24A)=Uiso(H24B)=Uiso(H24C)=FVAR(3) Uiso(H10D)=Uiso(H10E)=Uiso(H10F)=FVAR(4) Uiso(H17D)=Uiso(H17E)=Uiso(H17F)=FVAR(5) Uiso(H24D)=Uiso(H24E)=Uiso(H24F)=FVAR(6) 3.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C3(H3A,H3B), C1'(H1'A,H1'B), C3'(H3'A,H3'B) 3.b Aromatic/amide H refined with riding coordinates: C5(H5), C6(H6), C8(H8), C9(H9), C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C21(H21), C22(H22), C23(H23), C5'(H5'), C6'(H6'), C8'(H8'), C9'(H9'), C12'(H12'), C13'(H13'), C15'(H15'), C16'(H16'), C19'(H19'), C21'(H21'), C22'(H22'), C23'(H23') 3.c Idealised Me refined as rotating group: C10(H10A,H10B,H10C), C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C10'(H10D,H10E, H10F), C17'(H17D,H17E,H17F), C24'(H24D,H24E,H24F) ; _oslims_operator_name 'Dr A Batsanov' _oslims_operator_uuid 642c0cab-15e1-4db6-aabf-d1e3f44b6814 _oslims_submitter_name 'Mr Michele Ruggeri' _oslims_submitter_uuid 1a56f251-525c-414f-9d37-3e740585b168 _shelx_estimated_absorpt_t_min 0.891 _shelx_estimated_absorpt_t_max 0.983 _shelx_res_checksum 30622 _shelx_res_file ; TITL 19srv351_a.res in P-1 19srv351.res created by SHELXL-2018/3 at 19:26:34 on 28-Nov-2019 REM Old TITL 19srv351 in P-1 REM SHELXT solution in P-1: R1 0.113, Rweak 0.005, Alpha 0.027 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C48 N2 O6 S4 CELL 0.71073 5.9971 19.0997 20.3305 69.0014 87.1419 87.6311 ZERR 4 0.0002 0.0008 0.0008 0.0014 0.0016 0.0016 LATT 1 SFAC C H N O S UNIT 96 100 4 12 8 L.S. 7 0 0 PLAN 5 SIZE 0.064 0.099 0.436 TEMP -153.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.049600 0.480600 EXTI 0.002216 FVAR 0.14036 0.08345 0.04867 0.04687 0.08204 0.05438 0.05259 S1 5 -0.207044 0.314869 0.143476 11.00000 0.02319 0.01774 = 0.01666 -0.00581 -0.00160 0.00193 S2 5 0.104938 0.124785 0.373237 11.00000 0.03005 0.01928 = 0.01870 -0.00673 -0.00331 0.00374 O1 4 -0.055313 0.368807 0.098644 11.00000 0.03807 0.02130 = 0.02088 -0.00433 -0.00031 -0.00678 O2 4 -0.436659 0.335259 0.151683 11.00000 0.02802 0.02755 = 0.02875 -0.01127 -0.00469 0.01063 O3 4 0.289218 0.002462 0.192980 11.00000 0.02866 0.03431 = 0.03764 -0.02502 0.00836 -0.00919 N 3 -0.111381 0.288484 0.222710 11.00000 0.02034 0.02052 = 0.01536 -0.00669 -0.00003 0.00085 C1 1 0.112033 0.252596 0.242425 11.00000 0.01935 0.02081 = 0.01682 -0.00737 0.00015 0.00053 AFIX 23 H1A 2 0.232788 0.288463 0.236298 11.00000 -1.20000 H1B 2 0.155724 0.214774 0.220950 11.00000 -1.20000 AFIX 0 C2 1 0.012900 0.219167 0.318648 11.00000 0.01839 0.01813 = 0.01676 -0.00656 0.00185 0.00114 C3 1 -0.218507 0.230772 0.284927 11.00000 0.01822 0.02178 = 0.01661 -0.00673 0.00224 -0.00003 AFIX 23 H3A 2 -0.269859 0.186680 0.275680 11.00000 -1.20000 H3B 2 -0.336595 0.250846 0.309600 11.00000 -1.20000 AFIX 0 C4 1 0.037682 0.268121 0.362681 11.00000 0.02174 0.01749 = 0.01512 -0.00509 -0.00121 0.00339 C5 1 0.223620 0.311976 0.355184 11.00000 0.01832 0.02572 = 0.01830 -0.00813 0.00022 0.00206 AFIX 43 H5 2 0.341401 0.310749 0.322558 11.00000 -1.20000 AFIX 0 C6 1 0.239228 0.357496 0.394767 11.00000 0.02318 0.02427 = 0.02185 -0.00842 -0.00478 -0.00056 AFIX 43 H6 2 0.368039 0.386789 0.388860 11.00000 -1.20000 AFIX 0 C7 1 0.071179 0.361041 0.442568 11.00000 0.03119 0.01863 = 0.01639 -0.00523 -0.00667 0.00497 C8 1 -0.112450 0.315817 0.451659 11.00000 0.02722 0.02693 = 0.01725 -0.00977 0.00345 0.00195 AFIX 43 H8 2 -0.228262 0.316378 0.485110 11.00000 -1.20000 AFIX 0 C9 1 -0.128709 0.269845 0.412466 11.00000 0.02446 0.02218 = 0.01805 -0.00702 0.00283 -0.00261 AFIX 43 H9 2 -0.255023 0.239169 0.419720 11.00000 -1.20000 AFIX 0 C10 1 0.086945 0.413219 0.482956 11.00000 0.04561 0.03050 = 0.02850 -0.01844 -0.00458 0.00300 AFIX 137 H10A 2 0.214055 0.397616 0.513902 11.00000 21.00000 H10B 2 -0.050942 0.411363 0.511442 11.00000 21.00000 H10C 2 0.107957 0.464556 0.449746 11.00000 21.00000 AFIX 0 C11 1 -0.199999 0.237934 0.114920 11.00000 0.01953 0.01820 = 0.01371 -0.00560 -0.00153 0.00045 C12 1 -0.013694 0.223974 0.077762 11.00000 0.01782 0.02278 = 0.01610 -0.00448 0.00071 -0.00228 AFIX 43 H12 2 0.116202 0.252934 0.071086 11.00000 -1.20000 AFIX 0 C13 1 -0.019879 0.167074 0.050486 11.00000 0.02343 0.02403 = 0.01632 -0.00599 0.00215 0.00429 AFIX 43 H13 2 0.108152 0.156734 0.025708 11.00000 -1.20000 AFIX 0 C14 1 -0.209697 0.124938 0.058715 11.00000 0.02875 0.01780 = 0.01672 -0.00404 -0.00344 0.00217 C15 1 -0.391320 0.138672 0.098078 11.00000 0.02490 0.02376 = 0.02849 -0.00838 -0.00020 -0.00662 AFIX 43 H15 2 -0.520047 0.108980 0.105812 11.00000 -1.20000 AFIX 0 C16 1 -0.388153 0.194506 0.126071 11.00000 0.01807 0.02700 = 0.02200 -0.00908 0.00416 -0.00162 AFIX 43 H16 2 -0.513630 0.203225 0.152778 11.00000 -1.20000 AFIX 0 C17 1 -0.223363 0.067444 0.024268 11.00000 0.04346 0.02323 = 0.03015 -0.01232 -0.00602 0.00248 AFIX 137 H17A 2 -0.083991 0.066479 -0.002727 11.00000 31.00000 H17B 2 -0.348590 0.080558 -0.007485 11.00000 31.00000 H17C 2 -0.246402 0.017877 0.060599 11.00000 31.00000 AFIX 0 C18 1 0.030509 0.068789 0.324556 11.00000 0.02420 0.01670 = 0.01958 -0.00474 -0.00211 0.00018 C19 1 0.181711 0.056716 0.275759 11.00000 0.01803 0.01654 = 0.02470 -0.00725 -0.00098 -0.00208 AFIX 43 H19 2 0.324042 0.078973 0.267872 11.00000 -1.20000 AFIX 0 C20 1 0.125666 0.011914 0.238085 11.00000 0.02118 0.01699 = 0.02208 -0.00522 0.00091 0.00049 C21 1 -0.083373 -0.020477 0.249255 11.00000 0.02483 0.01721 = 0.02698 -0.00685 -0.00526 -0.00204 AFIX 43 H21 2 -0.123695 -0.050263 0.223211 11.00000 -1.20000 AFIX 0 C22 1 -0.231656 -0.008571 0.298970 11.00000 0.01960 0.02311 = 0.03555 -0.00448 -0.00026 -0.00539 AFIX 43 H22 2 -0.373862 -0.030928 0.307039 11.00000 -1.20000 AFIX 0 C23 1 -0.177433 0.035045 0.337042 11.00000 0.02315 0.02445 = 0.02698 -0.00594 0.00647 -0.00087 AFIX 43 H23 2 -0.280421 0.042022 0.371347 11.00000 -1.20000 AFIX 0 C24 1 0.235664 -0.036630 0.147958 11.00000 0.03901 0.03080 = 0.03933 -0.02418 -0.00455 0.00453 AFIX 137 H24A 2 0.123690 -0.007390 0.114858 11.00000 41.00000 H24B 2 0.175803 -0.085672 0.176493 11.00000 41.00000 H24C 2 0.370729 -0.043666 0.121611 11.00000 41.00000 AFIX 0 S1' 5 0.808734 0.804839 0.143096 11.00000 0.01766 0.01563 = 0.01713 -0.00759 -0.00009 -0.00223 S2' 5 0.427763 0.634880 0.372950 11.00000 0.03080 0.02337 = 0.01920 -0.00958 0.00209 -0.00724 O1' 4 1.046338 0.802598 0.149807 11.00000 0.01894 0.02784 = 0.02759 -0.01469 0.00055 -0.00624 O2' 4 0.698916 0.872247 0.099398 11.00000 0.03127 0.01674 = 0.02103 -0.00491 -0.00100 0.00160 O3' 4 0.220234 0.523807 0.193277 11.00000 0.03526 0.02281 = 0.04012 -0.02074 -0.01394 0.00483 N' 3 0.701682 0.787280 0.222683 11.00000 0.01628 0.02078 = 0.01609 -0.00855 -0.00245 0.00091 C1' 1 0.783959 0.725733 0.285776 11.00000 0.01722 0.02048 = 0.01687 -0.00717 -0.00380 0.00078 AFIX 23 H1'A 2 0.900435 0.740802 0.310551 11.00000 -1.20000 H1'B 2 0.828715 0.679149 0.277237 11.00000 -1.20000 AFIX 0 C2' 1 0.545308 0.724934 0.318935 11.00000 0.01811 0.01948 = 0.01712 -0.00812 -0.00409 -0.00064 C3' 1 0.467339 0.763444 0.242656 11.00000 0.01620 0.02604 = 0.01651 -0.00897 -0.00174 -0.00021 AFIX 23 H3'A 2 0.416141 0.728293 0.221040 11.00000 -1.20000 H3'B 2 0.358275 0.805432 0.236617 11.00000 -1.20000 AFIX 0 C4' 1 0.510413 0.774252 0.363172 11.00000 0.02232 0.01796 = 0.01441 -0.00601 -0.00026 -0.00384 C5' 1 0.669130 0.775825 0.410440 11.00000 0.02582 0.02281 = 0.01798 -0.00793 -0.00425 0.00061 AFIX 43 H5' 2 0.802258 0.745998 0.414996 11.00000 -1.20000 AFIX 0 C6' 1 0.633949 0.820636 0.450844 11.00000 0.02975 0.02613 = 0.01713 -0.00871 -0.00523 -0.00466 AFIX 43 H6' 2 0.743715 0.820923 0.482856 11.00000 -1.20000 AFIX 0 C7' 1 0.441877 0.865038 0.445493 11.00000 0.03068 0.01864 = 0.01628 -0.00677 0.00470 -0.00775 C8' 1 0.281107 0.861783 0.399630 11.00000 0.02360 0.02071 = 0.02259 -0.00883 0.00391 -0.00128 AFIX 43 H8' 2 0.146251 0.890591 0.396050 11.00000 -1.20000 AFIX 0 C9' 1 0.315122 0.817130 0.359172 11.00000 0.01933 0.02467 = 0.02005 -0.01040 -0.00147 -0.00354 AFIX 43 H9' 2 0.203238 0.815782 0.328202 11.00000 -1.20000 AFIX 0 C10' 1 0.407402 0.916426 0.486850 11.00000 0.04363 0.02931 = 0.02891 -0.01856 0.00641 -0.00792 AFIX 137 H10D 2 0.263513 0.906337 0.513083 11.00000 51.00000 H10E 2 0.408419 0.968714 0.454414 11.00000 51.00000 H10F 2 0.527852 0.907648 0.519952 11.00000 51.00000 AFIX 0 C11' 1 0.739597 0.733152 0.113156 11.00000 0.01860 0.01553 = 0.01253 -0.00620 0.00048 -0.00220 C12' 1 0.895425 0.676220 0.116679 11.00000 0.01815 0.02149 = 0.02126 -0.00914 -0.00498 0.00030 AFIX 43 H12' 2 1.033341 0.673422 0.138647 11.00000 -1.20000 AFIX 0 C13' 1 0.845971 0.623617 0.087567 11.00000 0.02814 0.01970 = 0.02828 -0.01218 -0.00325 0.00423 AFIX 43 H13' 2 0.952242 0.584731 0.089410 11.00000 -1.20000 AFIX 0 C14' 1 0.644908 0.626369 0.055779 11.00000 0.02878 0.02038 = 0.01490 -0.00714 0.00185 -0.00747 C15' 1 0.489406 0.682606 0.054773 11.00000 0.01963 0.03049 = 0.01670 -0.00961 -0.00240 -0.00639 AFIX 43 H15' 2 0.349181 0.684182 0.034447 11.00000 -1.20000 AFIX 0 C16' 1 0.534895 0.736386 0.082824 11.00000 0.01706 0.02397 = 0.01733 -0.00866 -0.00094 0.00113 AFIX 43 H16' 2 0.427890 0.774949 0.081386 11.00000 -1.20000 AFIX 0 C17' 1 0.600583 0.570753 0.021197 11.00000 0.04723 0.03066 = 0.03054 -0.01953 -0.00215 -0.00981 AFIX 137 H17D 2 0.665181 0.588504 -0.027009 11.00000 61.00000 H17E 2 0.439093 0.565617 0.019927 11.00000 61.00000 H17F 2 0.668650 0.521966 0.048183 11.00000 61.00000 AFIX 0 C18' 1 0.490764 0.576442 0.322754 11.00000 0.02385 0.01814 = 0.02054 -0.00645 -0.00013 -0.00332 C19' 1 0.338384 0.572078 0.275269 11.00000 0.01893 0.01717 = 0.02759 -0.00994 -0.00169 0.00086 AFIX 43 H19' 2 0.204699 0.601883 0.268071 11.00000 -1.20000 AFIX 0 C20' 1 0.381845 0.523891 0.238164 11.00000 0.02478 0.01639 = 0.02178 -0.00571 -0.00088 -0.00242 C21' 1 0.577285 0.480761 0.247902 11.00000 0.02695 0.01776 = 0.02516 -0.00665 0.00515 0.00183 AFIX 43 H21' 2 0.607655 0.448250 0.222301 11.00000 -1.20000 AFIX 0 C22' 1 0.728055 0.485667 0.295523 11.00000 0.02242 0.02428 = 0.03349 -0.00450 0.00038 0.00629 AFIX 43 H22' 2 0.862305 0.456167 0.302388 11.00000 -1.20000 AFIX 0 C23' 1 0.686560 0.532693 0.333177 11.00000 0.02373 0.02382 = 0.02819 -0.00389 -0.00664 -0.00025 AFIX 43 H23' 2 0.790816 0.535149 0.365918 11.00000 -1.20000 AFIX 0 C24' 1 0.220076 0.461959 0.169649 11.00000 0.06273 0.01903 = 0.03348 -0.01470 -0.01290 0.00305 AFIX 137 H24D 2 0.354813 0.462622 0.140125 11.00000 71.00000 H24E 2 0.087575 0.465777 0.142115 11.00000 71.00000 H24F 2 0.217733 0.414971 0.210466 11.00000 71.00000 AFIX 0 HKLF 4 REM 19srv351_a.res in P-1 REM wR2 = 0.1009, GooF = S = 1.050, Restrained GooF = 1.050 for all data REM R1 = 0.0386 for 8342 Fo > 4sig(Fo) and 0.0621 for all 11184 data REM 554 parameters refined using 0 restraints END WGHT 0.0484 0.5060 REM Highest difference peak 0.408, deepest hole -0.372, 1-sigma level 0.054 Q1 1 -0.2137 0.2781 0.1204 11.00000 0.05 0.41 Q2 1 0.5484 0.7472 0.3406 11.00000 0.05 0.35 Q3 1 0.7778 0.7679 0.1287 11.00000 0.05 0.33 Q4 1 0.6805 0.7194 0.3151 11.00000 0.05 0.32 Q5 1 0.4821 0.7397 0.2830 11.00000 0.05 0.31 ; _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. ; 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 -0.20704(7) 0.31487(2) 0.14348(2) 0.01933(9) Uani 1 1 d . . . . . S2 S 0.10494(7) 0.12479(2) 0.37324(2) 0.02273(10) Uani 1 1 d . . . . . O1 O -0.0553(2) 0.36881(6) 0.09864(6) 0.0275(3) Uani 1 1 d . . . . . O2 O -0.4367(2) 0.33526(6) 0.15168(6) 0.0280(3) Uani 1 1 d . . . . . O3 O 0.2892(2) 0.00246(7) 0.19298(6) 0.0303(3) Uani 1 1 d . . . . . N N -0.1114(2) 0.28848(7) 0.22271(6) 0.0187(3) Uani 1 1 d . . . . . C1 C 0.1120(3) 0.25260(8) 0.24242(8) 0.0189(3) Uani 1 1 d . . . . . H1A H 0.232788 0.288463 0.236298 0.023 Uiso 1 1 calc R U . . . H1B H 0.155724 0.214774 0.220950 0.023 Uiso 1 1 calc R U . . . C2 C 0.0129(3) 0.21917(8) 0.31865(8) 0.0178(3) Uani 1 1 d . . . . . C3 C -0.2185(3) 0.23077(8) 0.28493(8) 0.0190(3) Uani 1 1 d . . . . . H3A H -0.269859 0.186680 0.275680 0.023 Uiso 1 1 calc R U . . . H3B H -0.336595 0.250846 0.309600 0.023 Uiso 1 1 calc R U . . . C4 C 0.0377(3) 0.26812(8) 0.36268(8) 0.0184(3) Uani 1 1 d . . . . . C5 C 0.2236(3) 0.31198(9) 0.35518(8) 0.0208(3) Uani 1 1 d . . . . . H5 H 0.341401 0.310749 0.322558 0.025 Uiso 1 1 calc R U . . . C6 C 0.2392(3) 0.35750(9) 0.39477(8) 0.0229(3) Uani 1 1 d . . . . . H6 H 0.368039 0.386789 0.388860 0.027 Uiso 1 1 calc R U . . . C7 C 0.0712(3) 0.36104(9) 0.44257(8) 0.0223(3) Uani 1 1 d . . . . . C8 C -0.1125(3) 0.31582(9) 0.45166(8) 0.0235(3) Uani 1 1 d . . . . . H8 H -0.228262 0.316378 0.485110 0.028 Uiso 1 1 calc R U . . . C9 C -0.1287(3) 0.26985(9) 0.41247(8) 0.0217(3) Uani 1 1 d . . . . . H9 H -0.255023 0.239169 0.419720 0.026 Uiso 1 1 calc R U . . . C10 C 0.0869(3) 0.41322(10) 0.48296(9) 0.0327(4) Uani 1 1 d . . . . . H10A H 0.214055 0.397616 0.513902 0.083(5) Uiso 1 1 calc R U . . . H10B H -0.050942 0.411363 0.511442 0.083(5) Uiso 1 1 calc R U . . . H10C H 0.107957 0.464556 0.449746 0.083(5) Uiso 1 1 calc R U . . . C11 C -0.2000(3) 0.23793(8) 0.11492(8) 0.0172(3) Uani 1 1 d . . . . . C12 C -0.0137(3) 0.22397(9) 0.07776(8) 0.0196(3) Uani 1 1 d . . . . . H12 H 0.116202 0.252934 0.071086 0.023 Uiso 1 1 calc R U . . . C13 C -0.0199(3) 0.16707(9) 0.05049(8) 0.0218(3) Uani 1 1 d . . . . . H13 H 0.108152 0.156734 0.025708 0.026 Uiso 1 1 calc R U . . . C14 C -0.2097(3) 0.12494(9) 0.05872(8) 0.0217(3) Uani 1 1 d . . . . . C15 C -0.3913(3) 0.13867(9) 0.09808(9) 0.0258(4) Uani 1 1 d . . . . . H15 H -0.520047 0.108980 0.105812 0.031 Uiso 1 1 calc R U . . . C16 C -0.3882(3) 0.19451(9) 0.12607(8) 0.0224(3) Uani 1 1 d . . . . . H16 H -0.513630 0.203225 0.152778 0.027 Uiso 1 1 calc R U . . . C17 C -0.2234(3) 0.06744(9) 0.02427(9) 0.0314(4) Uani 1 1 d . . . . . H17A H -0.083991 0.066479 -0.002727 0.049(4) Uiso 1 1 calc R U . . . H17B H -0.348590 0.080558 -0.007485 0.049(4) Uiso 1 1 calc R U . . . H17C H -0.246402 0.017877 0.060599 0.049(4) Uiso 1 1 calc R U . . . C18 C 0.0305(3) 0.06879(8) 0.32456(8) 0.0206(3) Uani 1 1 d . . . . . C19 C 0.1817(3) 0.05672(8) 0.27576(8) 0.0197(3) Uani 1 1 d . . . . . H19 H 0.324042 0.078973 0.267872 0.024 Uiso 1 1 calc R U . . . C20 C 0.1257(3) 0.01191(8) 0.23809(8) 0.0207(3) Uani 1 1 d . . . . . C21 C -0.0834(3) -0.02048(9) 0.24925(9) 0.0231(3) Uani 1 1 d . . . . . H21 H -0.123695 -0.050263 0.223211 0.028 Uiso 1 1 calc R U . . . C22 C -0.2317(3) -0.00857(9) 0.29897(9) 0.0276(4) Uani 1 1 d . . . . . H22 H -0.373862 -0.030928 0.307039 0.033 Uiso 1 1 calc R U . . . C23 C -0.1774(3) 0.03504(9) 0.33704(9) 0.0260(4) Uani 1 1 d . . . . . H23 H -0.280421 0.042022 0.371347 0.031 Uiso 1 1 calc R U . . . C24 C 0.2357(3) -0.03663(10) 0.14796(10) 0.0332(4) Uani 1 1 d . . . . . H24A H 0.123690 -0.007390 0.114858 0.047(4) Uiso 1 1 calc R U . . . H24B H 0.175803 -0.085672 0.176493 0.047(4) Uiso 1 1 calc R U . . . H24C H 0.370729 -0.043666 0.121611 0.047(4) Uiso 1 1 calc R U . . . S1' S 0.80873(6) 0.80484(2) 0.14310(2) 0.01629(9) Uani 1 1 d . . . . . S2' S 0.42776(7) 0.63488(2) 0.37295(2) 0.02382(10) Uani 1 1 d . . . . . O1' O 1.04634(18) 0.80260(6) 0.14981(6) 0.0234(2) Uani 1 1 d . . . . . O2' O 0.6989(2) 0.87225(6) 0.09940(6) 0.0236(3) Uani 1 1 d . . . . . O3' O 0.2202(2) 0.52381(6) 0.19328(7) 0.0298(3) Uani 1 1 d . . . . . N' N 0.7017(2) 0.78728(7) 0.22268(6) 0.0172(3) Uani 1 1 d . . . . . C1' C 0.7840(3) 0.72573(8) 0.28578(8) 0.0180(3) Uani 1 1 d . . . . . H1'A H 0.900435 0.740802 0.310551 0.022 Uiso 1 1 calc R U . . . H1'B H 0.828715 0.679149 0.277237 0.022 Uiso 1 1 calc R U . . . C2' C 0.5453(3) 0.72493(8) 0.31893(8) 0.0177(3) Uani 1 1 d . . . . . C3' C 0.4673(3) 0.76344(9) 0.24266(8) 0.0192(3) Uani 1 1 d . . . . . H3'A H 0.416141 0.728293 0.221040 0.023 Uiso 1 1 calc R U . . . H3'B H 0.358275 0.805432 0.236617 0.023 Uiso 1 1 calc R U . . . C4' C 0.5104(3) 0.77425(8) 0.36317(8) 0.0181(3) Uani 1 1 d . . . . . C5' C 0.6691(3) 0.77582(9) 0.41044(8) 0.0219(3) Uani 1 1 d . . . . . H5' H 0.802258 0.745998 0.414996 0.026 Uiso 1 1 calc R U . . . C6' C 0.6339(3) 0.82064(9) 0.45084(8) 0.0238(4) Uani 1 1 d . . . . . H6' H 0.743715 0.820923 0.482856 0.029 Uiso 1 1 calc R U . . . C7' C 0.4419(3) 0.86504(9) 0.44549(8) 0.0217(3) Uani 1 1 d . . . . . C8' C 0.2811(3) 0.86178(9) 0.39963(8) 0.0221(3) Uani 1 1 d . . . . . H8' H 0.146251 0.890591 0.396050 0.027 Uiso 1 1 calc R U . . . C9' C 0.3151(3) 0.81713(9) 0.35917(8) 0.0206(3) Uani 1 1 d . . . . . H9' H 0.203238 0.815782 0.328202 0.025 Uiso 1 1 calc R U . . . C10' C 0.4074(3) 0.91643(10) 0.48685(9) 0.0318(4) Uani 1 1 d . . . . . H10D H 0.263513 0.906337 0.513083 0.082(5) Uiso 1 1 calc R U . . . H10E H 0.408419 0.968714 0.454414 0.082(5) Uiso 1 1 calc R U . . . H10F H 0.527852 0.907648 0.519952 0.082(5) Uiso 1 1 calc R U . . . C11' C 0.7396(3) 0.73315(8) 0.11316(7) 0.0152(3) Uani 1 1 d . . . . . C12' C 0.8954(3) 0.67622(8) 0.11668(8) 0.0198(3) Uani 1 1 d . . . . . H12' H 1.033341 0.673422 0.138647 0.024 Uiso 1 1 calc R U . . . C13' C 0.8460(3) 0.62362(9) 0.08757(9) 0.0244(4) Uani 1 1 d . . . . . H13' H 0.952242 0.584731 0.089410 0.029 Uiso 1 1 calc R U . . . C14' C 0.6449(3) 0.62637(9) 0.05578(8) 0.0210(3) Uani 1 1 d . . . . . C15' C 0.4894(3) 0.68261(9) 0.05477(8) 0.0217(3) Uani 1 1 d . . . . . H15' H 0.349181 0.684182 0.034447 0.026 Uiso 1 1 calc R U . . . C16' C 0.5349(3) 0.73639(9) 0.08282(8) 0.0191(3) Uani 1 1 d . . . . . H16' H 0.427890 0.774949 0.081386 0.023 Uiso 1 1 calc R U . . . C17' C 0.6006(3) 0.57075(10) 0.02120(10) 0.0335(4) Uani 1 1 d . . . . . H17D H 0.665181 0.588504 -0.027009 0.054(4) Uiso 1 1 calc R U . . . H17E H 0.439093 0.565617 0.019927 0.054(4) Uiso 1 1 calc R U . . . H17F H 0.668650 0.521966 0.048183 0.054(4) Uiso 1 1 calc R U . . . C18' C 0.4908(3) 0.57644(8) 0.32275(8) 0.0209(3) Uani 1 1 d . . . . . C19' C 0.3384(3) 0.57208(8) 0.27527(8) 0.0207(3) Uani 1 1 d . . . . . H19' H 0.204699 0.601883 0.268071 0.025 Uiso 1 1 calc R U . . . C20' C 0.3818(3) 0.52389(8) 0.23816(8) 0.0212(3) Uani 1 1 d . . . . . C21' C 0.5773(3) 0.48076(9) 0.24790(9) 0.0239(4) Uani 1 1 d . . . . . H21' H 0.607655 0.448250 0.222301 0.029 Uiso 1 1 calc R U . . . C22' C 0.7281(3) 0.48567(9) 0.29552(9) 0.0286(4) Uani 1 1 d . . . . . H22' H 0.862305 0.456167 0.302388 0.034 Uiso 1 1 calc R U . . . C23' C 0.6866(3) 0.53269(9) 0.33318(9) 0.0265(4) Uani 1 1 d . . . . . H23' H 0.790816 0.535149 0.365918 0.032 Uiso 1 1 calc R U . . . C24' C 0.2201(4) 0.46196(9) 0.16965(10) 0.0367(5) Uani 1 1 d . . . . . H24D H 0.354813 0.462622 0.140125 0.053(4) Uiso 1 1 calc R U . . . H24E H 0.087575 0.465777 0.142115 0.053(4) Uiso 1 1 calc R U . . . H24F H 0.217733 0.414971 0.210466 0.053(4) 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 0.0232(2) 0.01774(18) 0.01666(19) -0.00581(15) -0.00160(15) 0.00193(15) S2 0.0300(2) 0.01928(19) 0.0187(2) -0.00673(15) -0.00331(16) 0.00374(16) O1 0.0381(7) 0.0213(6) 0.0209(6) -0.0043(5) -0.0003(5) -0.0068(5) O2 0.0280(7) 0.0276(6) 0.0287(6) -0.0113(5) -0.0047(5) 0.0106(5) O3 0.0287(7) 0.0343(7) 0.0376(7) -0.0250(6) 0.0084(6) -0.0092(5) N 0.0203(7) 0.0205(6) 0.0154(6) -0.0067(5) 0.0000(5) 0.0008(5) C1 0.0194(8) 0.0208(7) 0.0168(7) -0.0074(6) 0.0002(6) 0.0005(6) C2 0.0184(8) 0.0181(7) 0.0168(7) -0.0066(6) 0.0018(6) 0.0011(6) C3 0.0182(8) 0.0218(8) 0.0166(7) -0.0067(6) 0.0022(6) 0.0000(6) C4 0.0217(8) 0.0175(7) 0.0151(7) -0.0051(6) -0.0012(6) 0.0034(6) C5 0.0183(8) 0.0257(8) 0.0183(8) -0.0081(6) 0.0002(6) 0.0021(6) C6 0.0232(9) 0.0243(8) 0.0219(8) -0.0084(7) -0.0048(7) -0.0006(7) C7 0.0312(10) 0.0186(8) 0.0164(8) -0.0052(6) -0.0067(7) 0.0050(7) C8 0.0272(9) 0.0269(8) 0.0173(8) -0.0098(7) 0.0035(7) 0.0020(7) C9 0.0245(9) 0.0222(8) 0.0181(8) -0.0070(6) 0.0028(6) -0.0026(6) C10 0.0456(12) 0.0305(9) 0.0285(10) -0.0184(8) -0.0046(8) 0.0030(8) C11 0.0195(8) 0.0182(7) 0.0137(7) -0.0056(6) -0.0015(6) 0.0005(6) C12 0.0178(8) 0.0228(8) 0.0161(7) -0.0045(6) 0.0007(6) -0.0023(6) C13 0.0234(9) 0.0240(8) 0.0163(8) -0.0060(6) 0.0021(6) 0.0043(7) C14 0.0287(9) 0.0178(7) 0.0167(8) -0.0040(6) -0.0034(6) 0.0022(6) C15 0.0249(9) 0.0238(8) 0.0285(9) -0.0084(7) -0.0002(7) -0.0066(7) C16 0.0181(8) 0.0270(8) 0.0220(8) -0.0091(7) 0.0042(6) -0.0016(6) C17 0.0435(12) 0.0232(9) 0.0302(10) -0.0123(7) -0.0060(8) 0.0025(8) C18 0.0242(9) 0.0167(7) 0.0196(8) -0.0047(6) -0.0021(6) 0.0002(6) C19 0.0180(8) 0.0165(7) 0.0247(8) -0.0072(6) -0.0010(6) -0.0021(6) C20 0.0212(8) 0.0170(7) 0.0221(8) -0.0052(6) 0.0009(6) 0.0005(6) C21 0.0248(9) 0.0172(7) 0.0270(9) -0.0069(6) -0.0053(7) -0.0020(6) C22 0.0196(9) 0.0231(8) 0.0355(10) -0.0045(7) -0.0003(7) -0.0054(7) C23 0.0231(9) 0.0245(8) 0.0270(9) -0.0059(7) 0.0065(7) -0.0009(7) C24 0.0390(11) 0.0308(10) 0.0393(11) -0.0242(8) -0.0045(9) 0.0045(8) S1' 0.0177(2) 0.01563(17) 0.01713(18) -0.00759(14) -0.00009(14) -0.00223(14) S2' 0.0308(2) 0.0234(2) 0.0192(2) -0.00958(16) 0.00209(16) -0.00724(17) O1' 0.0189(6) 0.0278(6) 0.0276(6) -0.0147(5) 0.0005(5) -0.0062(5) O2' 0.0313(7) 0.0167(5) 0.0210(6) -0.0049(4) -0.0010(5) 0.0016(5) O3' 0.0353(7) 0.0228(6) 0.0401(7) -0.0207(5) -0.0139(6) 0.0048(5) N' 0.0163(7) 0.0208(6) 0.0161(6) -0.0086(5) -0.0025(5) 0.0009(5) C1' 0.0172(8) 0.0205(7) 0.0169(7) -0.0072(6) -0.0038(6) 0.0008(6) C2' 0.0181(8) 0.0195(7) 0.0171(7) -0.0081(6) -0.0041(6) -0.0006(6) C3' 0.0162(8) 0.0260(8) 0.0165(7) -0.0090(6) -0.0017(6) -0.0002(6) C4' 0.0223(8) 0.0180(7) 0.0144(7) -0.0060(6) -0.0003(6) -0.0038(6) C5' 0.0258(9) 0.0228(8) 0.0180(8) -0.0079(6) -0.0043(6) 0.0006(7) C6' 0.0297(10) 0.0261(8) 0.0171(8) -0.0087(6) -0.0052(7) -0.0047(7) C7' 0.0307(9) 0.0186(7) 0.0163(8) -0.0068(6) 0.0047(7) -0.0078(7) C8' 0.0236(9) 0.0207(8) 0.0226(8) -0.0088(6) 0.0039(7) -0.0013(6) C9' 0.0193(8) 0.0247(8) 0.0200(8) -0.0104(6) -0.0015(6) -0.0035(6) C10' 0.0436(12) 0.0293(9) 0.0289(9) -0.0186(8) 0.0064(8) -0.0079(8) C11' 0.0186(8) 0.0155(7) 0.0125(7) -0.0062(6) 0.0005(6) -0.0022(6) C12' 0.0181(8) 0.0215(8) 0.0213(8) -0.0091(6) -0.0050(6) 0.0003(6) C13' 0.0281(9) 0.0197(8) 0.0283(9) -0.0122(7) -0.0033(7) 0.0042(7) C14' 0.0288(9) 0.0204(8) 0.0149(7) -0.0071(6) 0.0018(6) -0.0075(7) C15' 0.0196(8) 0.0305(9) 0.0167(8) -0.0096(7) -0.0024(6) -0.0064(7) C16' 0.0171(8) 0.0240(8) 0.0173(7) -0.0087(6) -0.0009(6) 0.0011(6) C17' 0.0472(12) 0.0307(9) 0.0305(10) -0.0195(8) -0.0022(8) -0.0098(8) C18' 0.0239(9) 0.0181(7) 0.0205(8) -0.0065(6) -0.0001(6) -0.0033(6) C19' 0.0189(8) 0.0172(7) 0.0276(9) -0.0099(6) -0.0017(7) 0.0009(6) C20' 0.0248(9) 0.0164(7) 0.0218(8) -0.0057(6) -0.0009(7) -0.0024(6) C21' 0.0269(9) 0.0178(8) 0.0252(9) -0.0067(6) 0.0052(7) 0.0018(7) C22' 0.0224(9) 0.0243(8) 0.0335(10) -0.0045(7) 0.0004(7) 0.0063(7) C23' 0.0237(9) 0.0238(8) 0.0282(9) -0.0039(7) -0.0066(7) -0.0003(7) C24' 0.0627(14) 0.0190(8) 0.0335(10) -0.0147(8) -0.0129(9) 0.0031(8) 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' N N 0.0061 0.0033 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.0350 0.00 0.00 -1.00 0.0290 0.00 -1.00 0.00 0.0230 0.00 1.00 0.00 0.0320 1.00 -1.00 1.00 0.1720 -1.00 1.00 -1.00 0.1910 -1.00 -1.00 1.00 0.1880 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 O1 S1 O2 120.62(7) . . ? O1 S1 N 106.27(7) . . ? O1 S1 C11 107.63(7) . . ? O2 S1 N 104.62(7) . . ? O2 S1 C11 107.80(7) . . ? N S1 C11 109.57(7) . . ? C18 S2 C2 103.43(7) . . ? C20 O3 C24 117.81(13) . . ? C1 N S1 124.31(10) . . ? C3 N S1 123.32(10) . . ? C3 N C1 91.00(11) . . ? N C1 H1A 114.2 . . ? N C1 H1B 114.2 . . ? N C1 C2 86.58(11) . . ? H1A C1 H1B 111.4 . . ? C2 C1 H1A 114.2 . . ? C2 C1 H1B 114.2 . . ? C1 C2 S2 118.04(10) . . ? C1 C2 C3 86.30(11) . . ? C3 C2 S2 119.24(11) . . ? C4 C2 S2 106.14(10) . . ? C4 C2 C1 114.41(12) . . ? C4 C2 C3 112.14(12) . . ? N C3 C2 86.44(11) . . ? N C3 H3A 114.2 . . ? N C3 H3B 114.2 . . ? C2 C3 H3A 114.2 . . ? C2 C3 H3B 114.2 . . ? H3A C3 H3B 111.4 . . ? C5 C4 C2 122.10(14) . . ? C5 C4 C9 117.87(14) . . ? C9 C4 C2 120.03(14) . . ? C4 C5 H5 119.6 . . ? C6 C5 C4 120.86(15) . . ? C6 C5 H5 119.6 . . ? C5 C6 H6 119.3 . . ? C7 C6 C5 121.32(16) . . ? C7 C6 H6 119.3 . . ? C6 C7 C8 118.08(15) . . ? C6 C7 C10 120.53(16) . . ? C8 C7 C10 121.39(16) . . ? C7 C8 H8 119.5 . . ? C9 C8 C7 120.90(15) . . ? C9 C8 H8 119.5 . . ? C4 C9 H9 119.5 . . ? C8 C9 C4 120.92(15) . . ? C8 C9 H9 119.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 S1 120.18(12) . . ? C12 C11 C16 120.51(14) . . ? C16 C11 S1 119.18(12) . . ? C11 C12 H12 120.5 . . ? C11 C12 C13 119.04(15) . . ? C13 C12 H12 120.5 . . ? C12 C13 H13 119.4 . . ? C12 C13 C14 121.30(15) . . ? C14 C13 H13 119.4 . . ? C13 C14 C15 118.31(15) . . ? C13 C14 C17 121.37(16) . . ? C15 C14 C17 120.29(16) . . ? C14 C15 H15 119.4 . . ? C16 C15 C14 121.29(16) . . ? C16 C15 H15 119.4 . . ? C11 C16 H16 120.3 . . ? C15 C16 C11 119.47(15) . . ? C15 C16 H16 120.3 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17B 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 S2 119.89(12) . . ? C19 C18 C23 119.92(15) . . ? C23 C18 S2 120.16(13) . . ? C18 C19 H19 119.9 . . ? C18 C19 C20 120.21(15) . . ? C20 C19 H19 119.9 . . ? O3 C20 C19 115.03(14) . . ? O3 C20 C21 124.93(14) . . ? C21 C20 C19 120.03(15) . . ? C20 C21 H21 120.5 . . ? C22 C21 C20 118.98(15) . . ? C22 C21 H21 120.5 . . ? C21 C22 H22 119.2 . . ? C23 C22 C21 121.54(16) . . ? C23 C22 H22 119.2 . . ? C18 C23 H23 120.4 . . ? C22 C23 C18 119.29(16) . . ? C22 C23 H23 120.4 . . ? O3 C24 H24A 109.5 . . ? O3 C24 H24B 109.5 . . ? O3 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O1' S1' N' 105.56(7) . . ? O1' S1' C11' 108.47(7) . . ? O2' S1' O1' 120.04(7) . . ? O2' S1' N' 105.96(7) . . ? O2' S1' C11' 107.12(7) . . ? N' S1' C11' 109.38(7) . . ? C18' S2' C2' 103.97(7) . . ? C20' O3' C24' 117.50(13) . . ? C1' N' S1' 123.54(10) . . ? C1' N' C3' 91.00(11) . . ? C3' N' S1' 122.48(10) . . ? N' C1' H1'A 114.2 . . ? N' C1' H1'B 114.2 . . ? N' C1' C2' 87.00(11) . . ? H1'A C1' H1'B 111.3 . . ? C2' C1' H1'A 114.2 . . ? C2' C1' H1'B 114.2 . . ? C1' C2' S2' 118.61(10) . . ? C3' C2' S2' 118.64(11) . . ? C3' C2' C1' 86.42(11) . . ? C4' C2' S2' 105.13(10) . . ? C4' C2' C1' 114.77(12) . . ? C4' C2' C3' 113.03(12) . . ? N' C3' C2' 87.06(11) . . ? N' C3' H3'A 114.1 . . ? N' C3' H3'B 114.1 . . ? C2' C3' H3'A 114.1 . . ? C2' C3' H3'B 114.1 . . ? H3'A C3' H3'B 111.3 . . ? C5' C4' C2' 121.15(14) . . ? C9' C4' C2' 120.59(13) . . ? C9' C4' C5' 118.22(14) . . ? C4' C5' H5' 119.8 . . ? C6' C5' C4' 120.45(16) . . ? C6' C5' H5' 119.8 . . ? C5' C6' H6' 119.3 . . ? C7' C6' C5' 121.38(15) . . ? C7' C6' H6' 119.3 . . ? C6' C7' C8' 117.99(14) . . ? C6' C7' C10' 121.61(15) . . ? C8' C7' C10' 120.40(16) . . ? C7' C8' H8' 119.6 . . ? C9' C8' C7' 120.90(16) . . ? C9' C8' H8' 119.6 . . ? C4' C9' H9' 119.5 . . ? C8' C9' C4' 121.02(15) . . ? C8' C9' H9' 119.5 . . ? C7' C10' H10D 109.5 . . ? C7' C10' H10E 109.5 . . ? C7' C10' H10F 109.5 . . ? H10D C10' H10E 109.5 . . ? H10D C10' H10F 109.5 . . ? H10E C10' H10F 109.5 . . ? C12' C11' S1' 119.35(11) . . ? C12' C11' C16' 120.93(13) . . ? C16' C11' S1' 119.62(11) . . ? C11' C12' H12' 120.6 . . ? C13' C12' C11' 118.73(14) . . ? C13' C12' H12' 120.6 . . ? C12' C13' H13' 119.2 . . ? C12' C13' C14' 121.52(15) . . ? C14' C13' H13' 119.2 . . ? C13' C14' C15' 118.58(14) . . ? C13' C14' C17' 120.33(15) . . ? C15' C14' C17' 121.07(15) . . ? C14' C15' H15' 119.4 . . ? C16' C15' C14' 121.21(15) . . ? C16' C15' H15' 119.4 . . ? C11' C16' H16' 120.5 . . ? C15' C16' C11' 118.99(14) . . ? C15' C16' H16' 120.5 . . ? C14' C17' H17D 109.5 . . ? C14' C17' H17E 109.5 . . ? C14' C17' H17F 109.5 . . ? H17D C17' H17E 109.5 . . ? H17D C17' H17F 109.5 . . ? H17E C17' H17F 109.5 . . ? C19' C18' S2' 119.54(12) . . ? C19' C18' C23' 119.92(15) . . ? C23' C18' S2' 120.47(13) . . ? C18' C19' H19' 120.1 . . ? C18' C19' C20' 119.88(15) . . ? C20' C19' H19' 120.1 . . ? O3' C20' C19' 114.89(14) . . ? O3' C20' C21' 124.71(14) . . ? C21' C20' C19' 120.40(15) . . ? C20' C21' H21' 120.4 . . ? C20' C21' C22' 119.11(15) . . ? C22' C21' H21' 120.4 . . ? C21' C22' H22' 119.4 . . ? C23' C22' C21' 121.20(16) . . ? C23' C22' H22' 119.4 . . ? C18' C23' H23' 120.3 . . ? C22' C23' C18' 119.48(16) . . ? C22' C23' H23' 120.3 . . ? O3' C24' H24D 109.5 . . ? O3' C24' H24E 109.5 . . ? O3' C24' H24F 109.5 . . ? H24D C24' H24E 109.5 . . ? H24D C24' H24F 109.5 . . ? H24E C24' H24F 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 O1 1.4289(12) . ? S1 O2 1.4335(12) . ? S1 N 1.6323(13) . ? S1 C11 1.7612(15) . ? S2 C2 1.8251(15) . ? S2 C18 1.7790(16) . ? O3 C20 1.360(2) . ? O3 C24 1.4274(19) . ? N C1 1.485(2) . ? N C3 1.4853(19) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.547(2) . ? C2 C3 1.551(2) . ? C2 C4 1.524(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.392(2) . ? C4 C9 1.393(2) . ? C5 H5 0.9500 . ? C5 C6 1.389(2) . ? C6 H6 0.9500 . ? C6 C7 1.381(2) . ? C7 C8 1.392(2) . ? C7 C10 1.509(2) . ? C8 H8 0.9500 . ? C8 C9 1.390(2) . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.388(2) . ? C11 C16 1.389(2) . ? C12 H12 0.9500 . ? C12 C13 1.388(2) . ? C13 H13 0.9500 . ? C13 C14 1.390(2) . ? C14 C15 1.391(2) . ? C14 C17 1.506(2) . ? C15 H15 0.9500 . ? C15 C16 1.378(2) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.384(2) . ? C18 C23 1.397(2) . ? C19 H19 0.9500 . ? C19 C20 1.397(2) . ? C20 C21 1.393(2) . ? C21 H21 0.9500 . ? C21 C22 1.387(2) . ? C22 H22 0.9500 . ? C22 C23 1.381(2) . ? C23 H23 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? S1' O1' 1.4356(12) . ? S1' O2' 1.4315(11) . ? S1' N' 1.6334(13) . ? S1' C11' 1.7569(14) . ? S2' C2' 1.8250(16) . ? S2' C18' 1.7813(16) . ? O3' C20' 1.3644(19) . ? O3' C24' 1.4258(18) . ? N' C1' 1.4850(18) . ? N' C3' 1.487(2) . ? C1' H1'A 0.9900 . ? C1' H1'B 0.9900 . ? C1' C2' 1.550(2) . ? C2' C3' 1.546(2) . ? C2' C4' 1.521(2) . ? C3' H3'A 0.9900 . ? C3' H3'B 0.9900 . ? C4' C5' 1.395(2) . ? C4' C9' 1.390(2) . ? C5' H5' 0.9500 . ? C5' C6' 1.387(2) . ? C6' H6' 0.9500 . ? C6' C7' 1.387(2) . ? C7' C8' 1.392(2) . ? C7' C10' 1.507(2) . ? C8' H8' 0.9500 . ? C8' C9' 1.385(2) . ? C9' H9' 0.9500 . ? C10' H10D 0.9800 . ? C10' H10E 0.9800 . ? C10' H10F 0.9800 . ? C11' C12' 1.388(2) . ? C11' C16' 1.390(2) . ? C12' H12' 0.9500 . ? C12' C13' 1.384(2) . ? C13' H13' 0.9500 . ? C13' C14' 1.387(2) . ? C14' C15' 1.388(2) . ? C14' C17' 1.507(2) . ? C15' H15' 0.9500 . ? C15' C16' 1.383(2) . ? C16' H16' 0.9500 . ? C17' H17D 0.9800 . ? C17' H17E 0.9800 . ? C17' H17F 0.9800 . ? C18' C19' 1.388(2) . ? C18' C23' 1.392(2) . ? C19' H19' 0.9500 . ? C19' C20' 1.394(2) . ? C20' C21' 1.385(2) . ? C21' H21' 0.9500 . ? C21' C22' 1.387(2) . ? C22' H22' 0.9500 . ? C22' C23' 1.382(2) . ? C23' H23' 0.9500 . ? C24' H24D 0.9800 . ? C24' H24E 0.9800 . ? C24' H24F 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 N C1 C2 -156.36(11) . . . . ? S1 N C3 C2 157.01(11) . . . . ? S1 C11 C12 C13 -174.38(11) . . . . ? S1 C11 C16 C15 173.93(12) . . . . ? S2 C2 C3 N -142.98(11) . . . . ? S2 C2 C4 C5 97.32(15) . . . . ? S2 C2 C4 C9 -82.55(15) . . . . ? S2 C18 C19 C20 179.06(11) . . . . ? S2 C18 C23 C22 -179.65(12) . . . . ? O1 S1 N C1 -59.93(13) . . . . ? O1 S1 N C3 -178.20(11) . . . . ? O1 S1 C11 C12 23.93(14) . . . . ? O1 S1 C11 C16 -151.96(12) . . . . ? O2 S1 N C1 171.43(12) . . . . ? O2 S1 N C3 53.15(13) . . . . ? O2 S1 C11 C12 155.49(12) . . . . ? O2 S1 C11 C16 -20.41(14) . . . . ? O3 C20 C21 C22 177.44(15) . . . . ? N S1 C11 C12 -91.22(13) . . . . ? N S1 C11 C16 92.89(13) . . . . ? N C1 C2 S2 144.08(11) . . . . ? N C1 C2 C3 22.73(10) . . . . ? N C1 C2 C4 -89.93(13) . . . . ? C1 N C3 C2 23.69(11) . . . . ? C1 C2 C3 N -22.74(10) . . . . ? C1 C2 C4 C5 -34.7(2) . . . . ? C1 C2 C4 C9 145.47(14) . . . . ? C2 S2 C18 C19 90.59(14) . . . . ? C2 S2 C18 C23 -91.43(14) . . . . ? C2 C4 C5 C6 178.37(14) . . . . ? C2 C4 C9 C8 -178.06(14) . . . . ? C3 N C1 C2 -23.75(11) . . . . ? C3 C2 C4 C5 -130.87(15) . . . . ? C3 C2 C4 C9 49.26(19) . . . . ? C4 C2 C3 N 92.15(13) . . . . ? C4 C5 C6 C7 -0.2(2) . . . . ? C5 C4 C9 C8 2.1(2) . . . . ? C5 C6 C7 C8 1.9(2) . . . . ? C5 C6 C7 C10 -177.51(15) . . . . ? C6 C7 C8 C9 -1.6(2) . . . . ? C7 C8 C9 C4 -0.4(2) . . . . ? C9 C4 C5 C6 -1.8(2) . . . . ? C10 C7 C8 C9 177.82(15) . . . . ? C11 S1 N C1 56.09(14) . . . . ? C11 S1 N C3 -62.19(13) . . . . ? C11 C12 C13 C14 1.1(2) . . . . ? C12 C11 C16 C15 -2.0(2) . . . . ? C12 C13 C14 C15 -3.0(2) . . . . ? C12 C13 C14 C17 175.03(15) . . . . ? C13 C14 C15 C16 2.5(2) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C16 C11 C12 C13 1.5(2) . . . . ? C17 C14 C15 C16 -175.55(15) . . . . ? C18 S2 C2 C1 -58.89(13) . . . . ? C18 S2 C2 C3 43.49(13) . . . . ? C18 S2 C2 C4 171.19(11) . . . . ? C18 C19 C20 O3 -178.38(14) . . . . ? C18 C19 C20 C21 0.3(2) . . . . ? C19 C18 C23 C22 -1.7(2) . . . . ? C19 C20 C21 C22 -1.2(2) . . . . ? C20 C21 C22 C23 0.6(2) . . . . ? C21 C22 C23 C18 0.9(3) . . . . ? C23 C18 C19 C20 1.1(2) . . . . ? C24 O3 C20 C19 -174.08(14) . . . . ? C24 O3 C20 C21 7.3(2) . . . . ? S1' N' C1' C2' -153.24(11) . . . . ? S1' N' C3' C2' 154.07(10) . . . . ? S1' C11' C12' C13' -174.67(12) . . . . ? S1' C11' C16' C15' 175.26(12) . . . . ? S2' C2' C3' N' -142.18(11) . . . . ? S2' C2' C4' C5' 88.76(15) . . . . ? S2' C2' C4' C9' -89.04(15) . . . . ? S2' C18' C19' C20' -177.08(12) . . . . ? S2' C18' C23' C22' 177.60(13) . . . . ? O1' S1' N' C1' -45.88(13) . . . . ? O1' S1' N' C3' -162.43(11) . . . . ? O1' S1' C11' C12' 15.38(14) . . . . ? O1' S1' C11' C16' -161.14(12) . . . . ? O2' S1' N' C1' -174.21(11) . . . . ? O2' S1' N' C3' 69.24(13) . . . . ? O2' S1' C11' C12' 146.31(12) . . . . ? O2' S1' C11' C16' -30.21(14) . . . . ? O3' C20' C21' C22' -179.64(15) . . . . ? N' S1' C11' C12' -99.28(13) . . . . ? N' S1' C11' C16' 84.20(13) . . . . ? N' C1' C2' S2' 142.24(10) . . . . ? N' C1' C2' C3' 21.38(10) . . . . ? N' C1' C2' C4' -92.37(13) . . . . ? C1' N' C3' C2' 22.29(11) . . . . ? C1' C2' C3' N' -21.35(10) . . . . ? C1' C2' C4' C5' -43.4(2) . . . . ? C1' C2' C4' C9' 138.81(14) . . . . ? C2' S2' C18' C19' -91.06(14) . . . . ? C2' S2' C18' C23' 91.87(14) . . . . ? C2' C4' C5' C6' -179.46(14) . . . . ? C2' C4' C9' C8' 179.52(14) . . . . ? C3' N' C1' C2' -22.24(10) . . . . ? C3' C2' C4' C5' -140.37(15) . . . . ? C3' C2' C4' C9' 41.8(2) . . . . ? C4' C2' C3' N' 94.09(13) . . . . ? C4' C5' C6' C7' -0.1(2) . . . . ? C5' C4' C9' C8' 1.7(2) . . . . ? C5' C6' C7' C8' 1.8(2) . . . . ? C5' C6' C7' C10' -177.23(15) . . . . ? C6' C7' C8' C9' -1.8(2) . . . . ? C7' C8' C9' C4' 0.0(2) . . . . ? C9' C4' C5' C6' -1.6(2) . . . . ? C10' C7' C8' C9' 177.29(15) . . . . ? C11' S1' N' C1' 70.63(13) . . . . ? C11' S1' N' C3' -45.92(13) . . . . ? C11' C12' C13' C14' -0.5(2) . . . . ? C12' C11' C16' C15' -1.2(2) . . . . ? C12' C13' C14' C15' -1.3(2) . . . . ? C12' C13' C14' C17' 176.80(15) . . . . ? C13' C14' C15' C16' 1.9(2) . . . . ? C14' C15' C16' C11' -0.7(2) . . . . ? C16' C11' C12' C13' 1.8(2) . . . . ? C17' C14' C15' C16' -176.17(15) . . . . ? C18' S2' C2' C1' -45.67(13) . . . . ? C18' S2' C2' C3' 56.86(13) . . . . ? C18' S2' C2' C4' -175.60(10) . . . . ? C18' C19' C20' O3' 179.63(14) . . . . ? C18' C19' C20' C21' -0.6(2) . . . . ? C19' C18' C23' C22' 0.5(2) . . . . ? C19' C20' C21' C22' 0.6(2) . . . . ? C20' C21' C22' C23' 0.0(3) . . . . ? C21' C22' C23' C18' -0.5(3) . . . . ? C23' C18' C19' C20' 0.0(2) . . . . ? C24' O3' C20' C19' -162.17(15) . . . . ? C24' O3' C20' C21' 18.1(2) . . . . ?