#------------------------------------------------------------------------------ #$Date: 2020-05-13 02:16:46 +0300 (Wed, 13 May 2020) $ #$Revision: 251990 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038345.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_4038345 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 O4 S' _chemical_formula_sum 'C24 H25 N O4 S' _chemical_formula_weight 423.51 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-09-25 _audit_creation_method ; Olex2 1.3-alpha (compiled 2019.09.11 svn.r3662 for OlexSys, GUI svn.r5938) ; _cell_angle_alpha 90 _cell_angle_beta 98.209(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.9761(8) _cell_length_b 11.2566(8) _cell_length_c 17.2670(13) _cell_measurement_reflns_used 4241 _cell_measurement_temperature 273.15 _cell_measurement_theta_max 20.76 _cell_measurement_theta_min 2.75 _cell_volume 2111.5(3) _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 multi-CPU (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 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device '3-circle area detector diffractometer' _diffrn_measurement_device_type 'Bruker D8 venture' _diffrn_measurement_method \w-scan _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 0.0775 _diffrn_reflns_av_unetI/netI 0.0604 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 32741 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.085 _diffrn_reflns_theta_max 25.085 _diffrn_reflns_theta_min 2.073 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\mS microsource' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.184 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8988 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker, 2016) was used for absorption correction. wR2(int) was 0.0616 before and 0.0526 after correction. The Ratio of minimum to maximum transmission is 0.8988. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.332 _exptl_crystal_description irregular _exptl_crystal_F_000 896 _exptl_crystal_size_max 0.131 _exptl_crystal_size_mid 0.122 _exptl_crystal_size_min 0.041 _refine_diff_density_max 0.276 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.044 _refine_ls_extinction_coef 0.0044(8) _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 1.030 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 324 _refine_ls_number_reflns 3761 _refine_ls_number_restraints 72 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0489 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0386P)^2^+1.4751P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1050 _refine_ls_wR_factor_ref 0.1210 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2460 _reflns_number_total 3761 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 19srv280.cif _cod_data_source_block 19srv280 _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 4038345 _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. Restrained distances O3C-C8C 1.4 with sigma of 0.02 C7C-C1B 1.44 with sigma of 0.02 O3C-C6B 1.4 with sigma of 0.02 C6B-O3C 1.4 with sigma of 0.02 C8C-C7C \\sim C8B-C7 with sigma of 0.02 C9B-C7C \\sim C9-C7 with sigma of 0.02 N-C9 \\sim N-C9B with sigma of 0.02 O3A-C8A \\sim O3B-C8B with sigma of 0.02 C8A-C7 \\sim C8B-C7 with sigma of 0.01 3. Uiso/Uaniso restraints and constraints Uanis(C2B) = Uanis(C2A) Uanis(C4B) = Uanis(C4A) Uanis(O4B) = Uanis(O4A) Uiso(C1B) = Uiso(C1A) Uanis(C9B) = Uanis(C9) Uiso(C8A) = Uiso(C8B) Uanis(C3B) = Uanis(C3A) Uanis(C5B) = Uanis(C5A) 4. Rigid body (RIGU) restrains O4A, C2A, C3A, C4A, C5A, C6A, C10A with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 O4B, C2B, C3B, C4B, C5B, C6B, C7B with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01 5. Others Uiso(H24A)=Uiso(H24B)=Uiso(H24C)=FVAR(1) Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=FVAR(2) Fixed Sof: C7(0.95) C8B(0.283) H8BA(0.283) H8BB(0.283) C9B(0.05) H9BA(0.05) H9BB(0.05) O3A(0.667) O4A(0.667) C1A(0.667) C2A(0.667) C3A(0.667) H3A(0.667) C4A(0.667) C5A(0.667) H5A(0.667) C6A(0.667) H6A(0.667) C10A(0.667) H10A(0.667) H10B(0.667) H10C(0.667) O3B(0.283) O4B(0.333) C1B(0.333) C2B(0.333) C3B(0.333) H3B(0.333) C4B(0.333) C5B(0.333) H5B(0.333) C6B(0.333) H6B(0.333) C7B(0.333) H7BA(0.333) H7BB(0.333) H7BC(0.333) O3C(0.05) C8C(0.05) H8CA(0.05) H8CB(0.05) C7C(0.05) C9(0.95) H9A(0.95) H9B(0.95) C8A(0.667) H8AA(0.667) H8AB(0.667) 6.a Riding coordinates: C8B(H8BA,H8BB), C9B(H9BA,H9BB), C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23), C3A(H3A), C5A(H5A), C6A(H6A), C3B(H3B), C5B(H5B), C6B(H6B), C8C(H8CA,H8CB), C9(H9A,H9B), C8A(H8AA,H8AB) 6.b Me refined with riding coordinates: C7B(H7BA,H7BB,H7BC) 6.c Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C24(H24A,H24B,H24C), C10A(H10A,H10B,H10C) ; _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 0.976 _shelx_estimated_absorpt_t_max 0.992 _shelx_res_checksum 32258 _shelx_res_file ; TITL 19srv280_a.res in P2(1)/n 19srv280.res created by SHELXL-2018/3 at 14:19:54 on 25-Sep-2019 REM Old TITL 19srv280 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.213, Rweak 0.017, Alpha 0.040 REM 0.531 for 212 systematic absences, Orientation as input REM Formula found by SHELXT: C25 N O3 S CELL 0.71073 10.9761 11.2566 17.267 90 98.209 90 ZERR 4 0.0008 0.0008 0.0013 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 96 100 4 16 4 EQIV $1 2-X,1-Y,1-Z DFIX 1.4 O3C C8C DFIX 1.44 C7C C1B DFIX 1.4 O3C C6B DFIX 1.4 C6B O3C SADI C8C C7C C8B C7 SADI C9B C7C C9 C7 SADI N C9 N C9B SADI O3A C8A O3B C8B SADI 0.01 C8A C7 C8B C7 RIGU 0.01 0.01 O4A C2A > C10A RIGU 0.01 0.01 O4B C2B > C7B EADP C2B C2A EADP C4B C4A EADP O4B O4A EADP C1B C1A EADP C9B C9 EADP C8A C8B EADP C3B C3A EADP C5B C5A L.S. 7 PLAN 10 SIZE 0.041 0.122 0.131 TEMP -153.15 HTAB N O1_$1 FREE C8B H9Bb FREE C8B H9Ba FREE C7 C7C FREE C9B C7 BIND C7C C1B BIND C7C C11 FREE C9 C7C FREE C9 C8C BIND O3C C6B BOND list 4 MORE -1 BOND $H fmap 2 53 acta CONF REM REM REM WGHT 0.038600 1.475100 EXTI 0.004355 FVAR 0.18067 0.10244 0.11921 S 5 1.020608 0.590212 0.385791 11.00000 0.02758 0.03276 = 0.05112 -0.00420 -0.00038 -0.00068 O1 4 1.097975 0.505850 0.432160 11.00000 0.03214 0.03534 = 0.05973 -0.00316 -0.00358 0.00529 O2 4 1.017922 0.590387 0.302833 11.00000 0.03947 0.04547 = 0.04485 -0.01106 0.00200 -0.00484 N 3 0.883581 0.562538 0.403514 11.00000 0.02890 0.03883 = 0.05098 0.00542 -0.00174 -0.00149 H 2 0.880755 0.543875 0.448113 11.00000 0.03080 C7 1 0.676964 0.539045 0.326164 10.95000 0.02584 0.02606 = 0.04356 -0.00043 0.00410 0.00039 PART 2 C8B 1 0.723041 0.473451 0.256950 10.28300 0.03377 AFIX 3 H8BA 2 0.702351 0.518821 0.209120 10.28300 -1.20000 H8BB 2 0.811751 0.464151 0.266990 10.28300 -1.20000 AFIX 0 PART 0 PART 3 C9B 1 0.793966 0.613579 0.341108 10.05000 0.02837 0.03079 = 0.05071 0.00061 0.00138 0.00129 AFIX 3 H9BA 2 0.802556 0.580009 0.290428 10.05000 -1.20000 H9BB 2 0.802616 0.699219 0.338918 10.05000 -1.20000 AFIX 0 PART 0 C11 1 0.561273 0.609794 0.292643 11.00000 0.02699 0.03018 = 0.04456 0.00161 0.00331 -0.00122 C12 1 0.570163 0.700600 0.239818 11.00000 0.02598 0.03783 = 0.05784 0.00673 0.00623 -0.00262 AFIX 3 H12 2 0.647193 0.720600 0.227258 11.00000 -1.20000 AFIX 0 C13 1 0.468884 0.762030 0.205398 11.00000 0.03864 0.03112 = 0.05826 0.01237 0.00287 -0.00259 AFIX 3 H13 2 0.478734 0.822551 0.170178 11.00000 -1.20000 AFIX 0 C14 1 0.351949 0.735627 0.222094 11.00000 0.03401 0.04071 = 0.05535 0.00513 0.00497 0.00767 C15 1 0.342065 0.644025 0.273698 11.00000 0.02589 0.05851 = 0.06581 0.01556 0.00946 0.00354 AFIX 3 H15 2 0.264705 0.623115 0.285298 11.00000 -1.20000 AFIX 0 C16 1 0.444582 0.582184 0.308781 11.00000 0.03333 0.04334 = 0.05852 0.01386 0.00623 -0.00036 AFIX 3 H16 2 0.434782 0.521214 0.343711 11.00000 -1.20000 AFIX 0 C17 1 0.240830 0.802430 0.183133 11.00000 0.03752 0.06874 = 0.08835 0.02637 0.00813 0.01813 AFIX 137 H17A 2 0.223508 0.869146 0.216358 11.00000 31.00000 H17B 2 0.169657 0.748977 0.175347 11.00000 31.00000 H17C 2 0.257068 0.832608 0.132360 11.00000 31.00000 AFIX 0 C18 1 1.064858 0.733329 0.420314 11.00000 0.02332 0.03221 = 0.04443 -0.00360 -0.00077 0.00207 C19 1 1.073268 0.823927 0.368075 11.00000 0.03388 0.04363 = 0.04461 -0.00196 0.00270 -0.00599 AFIX 3 H19 2 1.053298 0.810517 0.314625 11.00000 -1.20000 AFIX 0 C20 1 1.111562 0.935094 0.395390 11.00000 0.04249 0.03908 = 0.05571 0.00455 0.00426 -0.00578 AFIX 3 H20 2 1.116622 0.996513 0.359970 11.00000 -1.20000 AFIX 0 C21 1 1.142465 0.956397 0.474628 11.00000 0.03155 0.03605 = 0.05845 -0.00905 0.00008 0.00333 C22 1 1.130458 0.864655 0.526094 11.00000 0.05259 0.04282 = 0.04406 -0.01125 -0.00780 0.01285 AFIX 3 H22 2 1.148238 0.878445 0.579624 11.00000 -1.20000 AFIX 0 C23 1 1.092820 0.753440 0.499948 11.00000 0.04801 0.03531 = 0.04458 0.00158 0.00101 0.00856 AFIX 3 H23 2 1.086200 0.692360 0.535378 11.00000 -1.20000 AFIX 0 C24 1 1.190817 1.075983 0.504675 11.00000 0.04780 0.04395 = 0.08013 -0.01971 -0.00139 -0.00240 AFIX 137 H24A 2 1.280407 1.071774 0.518852 11.00000 21.00000 H24B 2 1.153179 1.097699 0.550857 11.00000 21.00000 H24C 2 1.170217 1.136016 0.463798 11.00000 21.00000 AFIX 0 PART 1 O3A 4 0.664928 0.345607 0.269655 10.66700 0.02771 0.02776 = 0.04638 -0.00773 -0.00245 0.00046 O4A 4 0.555918 0.133987 0.487567 10.66700 0.05423 0.03497 = 0.05817 0.00205 0.00471 -0.01065 C1A 1 0.648469 0.443569 0.385888 10.66700 0.02770 C2A 1 0.642879 0.337169 0.344071 10.66700 0.01570 0.03600 = 0.04588 0.00310 -0.00834 0.00410 C3A 1 0.604783 0.234992 0.377731 10.66700 0.03167 0.02850 = 0.04468 -0.01234 0.00234 0.00018 AFIX 3 H3A 2 0.592003 0.164872 0.349241 10.66700 -1.20000 AFIX 0 C4A 1 0.586171 0.240375 0.455742 10.66700 0.03140 0.02709 = 0.04709 -0.00133 0.00173 -0.00271 C5A 1 0.599774 0.345865 0.497560 10.66700 0.04106 0.03171 = 0.03909 -0.00737 0.00823 -0.00239 AFIX 3 H5A 2 0.588104 0.347675 0.549850 10.66700 -1.20000 AFIX 0 C6A 1 0.631338 0.449939 0.460245 10.66700 0.02863 0.03178 = 0.06338 0.00013 0.00091 -0.00026 AFIX 3 H6A 2 0.640018 0.521759 0.487085 10.66700 -1.20000 AFIX 0 C10A 1 0.549683 0.130832 0.569997 10.66700 0.05746 0.04518 = 0.05921 0.00187 0.01236 -0.01065 AFIX 137 H10A 2 0.482255 0.181844 0.581642 10.66700 -1.50000 H10B 2 0.627585 0.159410 0.598791 10.66700 -1.50000 H10C 2 0.534952 0.049086 0.585847 10.66700 -1.50000 AFIX 0 PART 0 PART 2 O3B 4 0.663974 0.357761 0.248882 10.28300 0.03461 O4B 4 0.512950 0.110229 0.441251 10.33300 0.05423 0.03497 = 0.05817 0.00205 0.00471 -0.01065 C1B 1 0.645713 0.435843 0.367383 10.33300 0.02770 C2B 1 0.625553 0.337766 0.326375 10.33300 0.01570 0.03600 = 0.04588 0.00310 -0.00834 0.00410 C3B 1 0.592751 0.221215 0.341654 10.33300 0.03167 0.02850 = 0.04468 -0.01234 0.00234 0.00018 AFIX 3 H3B 2 0.592331 0.157935 0.306994 10.33300 -1.20000 AFIX 0 C4B 1 0.561086 0.213987 0.415415 10.33300 0.03140 0.02709 = 0.04709 -0.00133 0.00173 -0.00271 C5B 1 0.575522 0.304605 0.470078 10.33300 0.04106 0.03171 = 0.03909 -0.00737 0.00823 -0.00239 AFIX 3 H5B 2 0.558872 0.290915 0.520638 10.33300 -1.20000 AFIX 0 C6B 1 0.615686 0.418349 0.449110 10.33300 0.03624 AFIX 3 H6B 2 0.623296 0.480609 0.484880 10.33300 -1.20000 AFIX 0 C7B 1 0.481788 0.016095 0.385516 10.33300 0.07969 0.03699 = 0.05765 0.00283 0.00191 -0.01583 AFIX 33 H7BA 2 0.448916 -0.051623 0.411594 10.33300 -1.50000 H7BB 2 0.419603 0.044427 0.343138 10.33300 -1.50000 H7BC 2 0.555630 -0.008605 0.363872 10.33300 -1.50000 AFIX 0 PART 0 PART 3 O3C 4 0.627086 0.535751 0.502350 10.05000 0.03754 C8C 1 0.677310 0.614268 0.454410 10.05000 0.04284 AFIX 3 H8CA 2 0.763100 0.625978 0.475780 10.05000 -1.20000 H8CB 2 0.636170 0.690178 0.456780 10.05000 -1.20000 AFIX 0 C7C 1 0.671150 0.579021 0.367099 10.05000 0.04019 PART 0 PART 1 C9 1 0.774917 0.625768 0.364909 10.95000 0.02837 0.03079 = 0.05071 0.00061 0.00138 0.00129 AFIX 3 H9A 2 0.799097 0.678868 0.325559 10.95000 -1.20000 H9B 2 0.740327 0.673478 0.403179 10.95000 -1.20000 AFIX 0 C8A 1 0.723400 0.461802 0.263729 10.66700 0.03377 AFIX 3 H8AA 2 0.699930 0.495662 0.212109 10.66700 -1.20000 H8AB 2 0.812340 0.454622 0.273539 10.66700 -1.20000 AFIX 0 HKLF 4 REM 19srv280_a.res in P2(1)/n REM wR2 = 0.1210, GooF = S = 1.030, Restrained GooF = 1.020 for all data REM R1 = 0.0489 for 2460 Fo > 4sig(Fo) and 0.0914 for all 3761 data REM 324 parameters refined using 72 restraints END WGHT 0.0371 1.5208 REM Highest difference peak 0.276, deepest hole -0.280, 1-sigma level 0.044 Q1 1 0.7129 0.4854 0.3013 11.00000 0.05 0.28 Q2 1 0.6551 0.5998 0.5611 11.00000 0.05 0.24 Q3 1 0.7248 0.4728 0.2208 11.00000 0.05 0.24 Q4 1 0.6461 0.5959 0.4819 11.00000 0.05 0.23 Q5 1 1.0320 0.6713 0.4049 11.00000 0.05 0.23 Q6 1 0.3500 0.7477 0.2812 11.00000 0.05 0.23 Q7 1 0.6617 0.4943 0.3608 11.00000 0.05 0.21 Q8 1 0.2143 0.7556 0.1208 11.00000 0.05 0.20 Q9 1 1.2484 1.1129 0.4593 11.00000 0.05 0.20 Q10 1 0.2542 0.8869 0.1542 11.00000 0.05 0.18 ; _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+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 S S 1.02061(6) 0.59021(6) 0.38579(4) 0.0377(2) Uani 1 1 d . . . . . O1 O 1.09797(16) 0.50585(16) 0.43216(11) 0.0434(5) Uani 1 1 d . . . . . O2 O 1.01792(16) 0.59039(17) 0.30283(11) 0.0437(5) Uani 1 1 d . . . . . N N 0.8836(2) 0.5625(2) 0.40351(17) 0.0403(6) Uani 1 1 d D . . . . H H 0.881(2) 0.544(2) 0.4481(16) 0.031(9) Uiso 1 1 d . . . . . C7 C 0.6770(2) 0.5390(2) 0.32616(18) 0.0319(7) Uani 0.95 1 d D . P A . C8B C 0.723(2) 0.4735(14) 0.2569(10) 0.0338(9) Uiso 0.283 1 d D . P A 2 H8BA H 0.702351 0.518821 0.209120 0.041 Uiso 0.283 1 d R U P A 2 H8BB H 0.811751 0.464151 0.266990 0.041 Uiso 0.283 1 d R U P A 2 C9B C 0.794(4) 0.614(7) 0.341(3) 0.0370(9) Uani 0.05 1 d D . P B 3 H9BA H 0.802556 0.580009 0.290428 0.044 Uiso 0.05 1 d R U P B 3 H9BB H 0.802616 0.699219 0.338918 0.044 Uiso 0.05 1 d R U P B 3 C11 C 0.5613(2) 0.6098(2) 0.29264(16) 0.0341(6) Uani 1 1 d . . . . . C12 C 0.5702(2) 0.7006(2) 0.23982(17) 0.0405(7) Uani 1 1 d . . . . . H12 H 0.647193 0.720600 0.227258 0.049 Uiso 1 1 d R U . . . C13 C 0.4689(2) 0.7620(2) 0.20540(17) 0.0431(7) Uani 1 1 d . . . . . H13 H 0.478734 0.822551 0.170178 0.052 Uiso 1 1 d R U . . . C14 C 0.3519(2) 0.7356(3) 0.22209(17) 0.0435(7) Uani 1 1 d . . . . . C15 C 0.3421(3) 0.6440(3) 0.27370(18) 0.0498(8) Uani 1 1 d . . . . . H15 H 0.264705 0.623115 0.285298 0.060 Uiso 1 1 d R U . . . C16 C 0.4446(2) 0.5822(3) 0.30878(17) 0.0451(8) Uani 1 1 d . . . . . H16 H 0.434782 0.521214 0.343711 0.054 Uiso 1 1 d R U . . . C17 C 0.2408(3) 0.8024(3) 0.1831(2) 0.0650(10) Uani 1 1 d . . . . . H17A H 0.223508 0.869146 0.216358 0.119(9) Uiso 1 1 calc R U . . . H17B H 0.169657 0.748977 0.175347 0.119(9) Uiso 1 1 calc R U . . . H17C H 0.257068 0.832608 0.132360 0.119(9) Uiso 1 1 calc R U . . . C18 C 1.0649(2) 0.7333(2) 0.42031(16) 0.0339(6) Uani 1 1 d . . . . . C19 C 1.0733(2) 0.8239(2) 0.36808(17) 0.0410(7) Uani 1 1 d . . . . . H19 H 1.053298 0.810517 0.314625 0.049 Uiso 1 1 d R U . . . C20 C 1.1116(3) 0.9351(3) 0.39539(18) 0.0460(8) Uani 1 1 d . . . . . H20 H 1.116622 0.996513 0.359970 0.055 Uiso 1 1 d R U . . . C21 C 1.1425(2) 0.9564(3) 0.47463(18) 0.0426(7) Uani 1 1 d . . . . . C22 C 1.1305(3) 0.8647(3) 0.52609(18) 0.0479(8) Uani 1 1 d . . . . . H22 H 1.148238 0.878445 0.579624 0.058 Uiso 1 1 d R U . . . C23 C 1.0928(3) 0.7534(3) 0.49995(17) 0.0432(7) Uani 1 1 d . . . . . H23 H 1.086200 0.692360 0.535378 0.052 Uiso 1 1 d R U . . . C24 C 1.1908(3) 1.0760(3) 0.5047(2) 0.0583(9) Uani 1 1 d . . . . . H24A H 1.280407 1.071774 0.518852 0.102(8) Uiso 1 1 calc R U . . . H24B H 1.153179 1.097699 0.550857 0.102(8) Uiso 1 1 calc R U . . . H24C H 1.170217 1.136016 0.463798 0.102(8) Uiso 1 1 calc R U . . . O3A O 0.6649(6) 0.3456(5) 0.2697(4) 0.0347(14) Uani 0.667 1 d D . P A 1 O4A O 0.5559(3) 0.1340(3) 0.4876(2) 0.0494(8) Uani 0.667 1 d . . P A 1 C1A C 0.6485(5) 0.4436(5) 0.3859(3) 0.0277(9) Uiso 0.667 1 d . . P A 1 C2A C 0.6429(18) 0.337(2) 0.3441(11) 0.034(2) Uani 0.667 1 d . . P A 1 C3A C 0.6048(5) 0.2350(5) 0.3777(3) 0.0353(13) Uani 0.667 1 d . . P A 1 H3A H 0.592003 0.164872 0.349241 0.042 Uiso 0.667 1 d R U P A 1 C4A C 0.5862(4) 0.2404(5) 0.4557(3) 0.0356(11) Uani 0.667 1 d . . P A 1 C5A C 0.5998(5) 0.3459(4) 0.4976(3) 0.0370(11) Uani 0.667 1 d . . P A 1 H5A H 0.588104 0.347675 0.549850 0.044 Uiso 0.667 1 d R U P A 1 C6A C 0.6313(7) 0.4499(7) 0.4602(5) 0.0418(17) Uani 0.667 1 d . . P A 1 H6A H 0.640018 0.521759 0.487085 0.050 Uiso 0.667 1 d R U P A 1 C10A C 0.5497(4) 0.1308(4) 0.5700(3) 0.0536(12) Uani 0.667 1 d . . P A 1 H10A H 0.482255 0.181844 0.581642 0.080 Uiso 0.667 1 calc R U P A 1 H10B H 0.627585 0.159410 0.598791 0.080 Uiso 0.667 1 calc R U P A 1 H10C H 0.534952 0.049086 0.585847 0.080 Uiso 0.667 1 calc R U P A 1 O3B O 0.6640(18) 0.3578(15) 0.2489(10) 0.035(5) Uiso 0.283 1 d D . P A 2 O4B O 0.5129(6) 0.1102(6) 0.4413(4) 0.0494(8) Uani 0.333 1 d . . P A 2 C1B C 0.6457(10) 0.4358(11) 0.3674(6) 0.0277(9) Uiso 0.333 1 d . . P A 2 C2B C 0.626(4) 0.338(5) 0.326(3) 0.034(2) Uani 0.333 1 d . . P A 2 C3B C 0.5928(12) 0.2212(12) 0.3417(6) 0.0353(13) Uani 0.333 1 d . . P A 2 H3B H 0.592331 0.157935 0.306994 0.042 Uiso 0.333 1 d R U P A 2 C4B C 0.5611(10) 0.2140(10) 0.4154(7) 0.0356(11) Uani 0.333 1 d . . P A 2 C5B C 0.5755(12) 0.3046(12) 0.4701(7) 0.0370(11) Uani 0.333 1 d . . P A 2 H5B H 0.558872 0.290915 0.520638 0.044 Uiso 0.333 1 d R U P A 2 C6B C 0.6157(15) 0.4183(13) 0.4491(10) 0.036(5) Uiso 0.333 1 d . . P A 2 H6B H 0.623296 0.480609 0.484880 0.043 Uiso 0.333 1 d R U P A 2 C7B C 0.4818(10) 0.0161(8) 0.3855(6) 0.059(3) Uani 0.333 1 d . . P A 2 H7BA H 0.448916 -0.051623 0.411594 0.088 Uiso 0.333 1 calc R U P A 2 H7BB H 0.419603 0.044427 0.343138 0.088 Uiso 0.333 1 calc R U P A 2 H7BC H 0.555630 -0.008605 0.363872 0.088 Uiso 0.333 1 calc R U P A 2 O3C O 0.627(3) 0.536(3) 0.502(2) 0.038(9) Uiso 0.05 1 d D . P B 3 C8C C 0.677(5) 0.614(4) 0.454(2) 0.043(14) Uiso 0.05 1 d D . P B 3 H8CA H 0.763100 0.625978 0.475780 0.051 Uiso 0.05 1 d R U P B 3 H8CB H 0.636170 0.690178 0.456780 0.051 Uiso 0.05 1 d R U P B 3 C7C C 0.671(5) 0.579(5) 0.367(3) 0.040(16) Uiso 0.05 1 d D . P B 3 C9 C 0.7749(3) 0.6258(3) 0.36491(17) 0.0370(9) Uani 0.95 1 d D . P A 1 H9A H 0.799097 0.678868 0.325559 0.044 Uiso 0.95 1 d R U P A 1 H9B H 0.740327 0.673478 0.403179 0.044 Uiso 0.95 1 d R U P A 1 C8A C 0.7234(9) 0.4618(6) 0.2637(4) 0.0338(9) Uiso 0.667 1 d D . P A 1 H8AA H 0.699930 0.495662 0.212109 0.041 Uiso 0.667 1 d R U P A 1 H8AB H 0.812340 0.454622 0.273539 0.041 Uiso 0.667 1 d R U P A 1 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 S 0.0276(4) 0.0328(4) 0.0511(5) -0.0042(3) -0.0004(3) -0.0007(3) O1 0.0321(10) 0.0353(11) 0.0597(13) -0.0032(9) -0.0036(9) 0.0053(9) O2 0.0395(11) 0.0455(12) 0.0449(13) -0.0111(10) 0.0020(9) -0.0048(9) N 0.0289(13) 0.0388(15) 0.0510(18) 0.0054(13) -0.0017(12) -0.0015(10) C7 0.0258(15) 0.0261(15) 0.0436(19) -0.0004(14) 0.0041(13) 0.0004(12) C9B 0.0284(17) 0.0308(18) 0.051(2) 0.0006(17) 0.0014(14) 0.0013(13) C11 0.0270(14) 0.0302(15) 0.0446(17) 0.0016(13) 0.0033(12) -0.0012(11) C12 0.0260(15) 0.0378(16) 0.058(2) 0.0067(15) 0.0062(13) -0.0026(12) C13 0.0386(16) 0.0311(16) 0.058(2) 0.0124(14) 0.0029(14) -0.0026(13) C14 0.0340(16) 0.0407(17) 0.055(2) 0.0051(15) 0.0050(14) 0.0077(13) C15 0.0259(15) 0.059(2) 0.066(2) 0.0156(17) 0.0095(14) 0.0035(14) C16 0.0333(16) 0.0433(17) 0.059(2) 0.0139(15) 0.0062(14) -0.0004(14) C17 0.0375(18) 0.069(2) 0.088(3) 0.026(2) 0.0081(17) 0.0181(17) C18 0.0233(13) 0.0322(15) 0.0444(18) -0.0036(13) -0.0008(12) 0.0021(11) C19 0.0339(15) 0.0436(18) 0.0446(18) -0.0020(14) 0.0027(13) -0.0060(13) C20 0.0425(17) 0.0391(18) 0.056(2) 0.0045(15) 0.0043(14) -0.0058(14) C21 0.0315(15) 0.0360(16) 0.058(2) -0.0091(15) 0.0001(13) 0.0033(13) C22 0.0526(19) 0.0428(18) 0.0441(19) -0.0113(15) -0.0078(15) 0.0128(15) C23 0.0480(17) 0.0353(16) 0.0446(19) 0.0016(14) 0.0010(14) 0.0086(14) C24 0.0478(19) 0.0440(19) 0.080(2) -0.0197(17) -0.0014(16) -0.0024(15) O3A 0.028(2) 0.028(2) 0.046(5) -0.008(3) -0.002(3) 0.0005(15) O4A 0.054(2) 0.0350(16) 0.058(3) 0.0020(17) 0.0047(17) -0.0106(14) C2A 0.016(6) 0.0360(18) 0.046(9) 0.003(5) -0.008(4) 0.004(4) C3A 0.032(2) 0.028(2) 0.045(4) -0.012(3) 0.002(3) 0.0002(17) C4A 0.031(2) 0.027(3) 0.047(4) -0.001(3) 0.002(2) -0.003(2) C5A 0.041(3) 0.032(3) 0.039(4) -0.007(2) 0.008(2) -0.002(2) C6A 0.029(3) 0.032(4) 0.063(4) 0.000(4) 0.001(3) 0.000(3) C10A 0.057(3) 0.045(3) 0.059(3) 0.002(2) 0.012(2) -0.011(2) O4B 0.054(2) 0.0350(16) 0.058(3) 0.0020(17) 0.0047(17) -0.0106(14) C2B 0.016(6) 0.0360(18) 0.046(9) 0.003(5) -0.008(4) 0.004(4) C3B 0.032(2) 0.028(2) 0.045(4) -0.012(3) 0.002(3) 0.0002(17) C4B 0.031(2) 0.027(3) 0.047(4) -0.001(3) 0.002(2) -0.003(2) C5B 0.041(3) 0.032(3) 0.039(4) -0.007(2) 0.008(2) -0.002(2) C7B 0.080(7) 0.037(5) 0.058(6) 0.003(5) 0.002(5) -0.016(5) C9 0.0284(17) 0.0308(18) 0.051(2) 0.0006(17) 0.0014(14) 0.0013(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' 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 -1.00 0.00 1.00 0.0120 1.00 0.00 -1.00 0.0200 1.00 1.00 1.00 0.0430 -1.00 -1.00 -1.00 0.0560 -1.00 0.00 -1.00 0.0370 1.00 1.00 -1.00 0.0490 -1.00 -1.00 1.00 0.0300 -1.00 -2.00 2.00 0.0370 1.00 2.00 -2.00 0.0510 -2.00 2.00 -1.00 0.0510 2.00 -2.00 1.00 0.0510 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 S N 105.08(13) . . ? O1 S C18 107.64(12) . . ? O2 S O1 119.01(12) . . ? O2 S N 107.77(13) . . ? O2 S C18 107.65(13) . . ? N S C18 109.45(13) . . ? S N H 113(2) . . ? C9B N S 109(2) . . ? C9B N H 134(3) . . ? C9 N S 122.8(2) . . ? C9 N H 115(2) . . ? C11 C7 C8B 107.4(9) . . ? C11 C7 C1A 112.0(3) . . ? C1B C7 C8B 97.2(8) . . ? C1B C7 C11 111.3(5) . . ? C9 C7 C11 108.9(2) . . ? C9 C7 C1A 110.3(3) . . ? C8A C7 C11 111.7(4) . . ? C8A C7 C1A 101.2(4) . . ? C8A C7 C9 112.7(4) . . ? C7 C8B H8BA 110.1 . . ? C7 C8B H8BB 110.1 . . ? H8BA C8B H8BB 108.4 . . ? O3B C8B C7 108.1(12) . . ? O3B C8B H8BA 110.1 . . ? O3B C8B H8BB 110.1 . . ? N C9B H9BA 111.6 . . ? N C9B H9BB 111.0 . . ? N C9B C7C 102(3) . . ? H9BA C9B H9BB 109.2 . . ? C7C C9B H9BA 111.6 . . ? C7C C9B H9BB 111.1 . . ? C7 C11 C7C 30.3(17) . . ? C12 C11 C7 119.9(2) . . ? C12 C11 C16 116.9(2) . . ? C12 C11 C7C 123(2) . . ? C16 C11 C7 123.0(2) . . ? C16 C11 C7C 112.7(17) . . ? C11 C12 H12 119.0 . . ? C13 C12 C11 122.0(3) . . ? C13 C12 H12 119.0 . . ? C12 C13 H13 119.4 . . ? C12 C13 C14 121.3(3) . . ? C14 C13 H13 119.4 . . ? C13 C14 C17 120.9(3) . . ? C15 C14 C13 117.1(3) . . ? C15 C14 C17 121.9(3) . . ? C14 C15 H15 119.2 . . ? C14 C15 C16 121.6(3) . . ? C16 C15 H15 119.2 . . ? C11 C16 C15 121.0(3) . . ? C11 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? 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 S 119.9(2) . . ? C19 C18 C23 120.3(3) . . ? C23 C18 S 119.8(2) . . ? C18 C19 H19 120.2 . . ? C18 C19 C20 119.6(3) . . ? C20 C19 H19 120.2 . . ? C19 C20 H20 119.5 . . ? C19 C20 C21 121.0(3) . . ? C21 C20 H20 119.5 . . ? C20 C21 C24 121.2(3) . . ? C22 C21 C20 118.3(3) . . ? C22 C21 C24 120.4(3) . . ? C21 C22 H22 119.3 . . ? C23 C22 C21 121.4(3) . . ? C23 C22 H22 119.3 . . ? C18 C23 H23 120.4 . . ? C22 C23 C18 119.3(3) . . ? C22 C23 H23 120.4 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24B 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C2A O3A C8A 105.7(11) . . ? C4A O4A C10A 117.7(4) . . ? C2A C1A C7 104.4(10) . . ? C6A C1A C7 132.5(6) . . ? C6A C1A C2A 123.1(11) . . ? O3A C2A C1A 115.7(17) . . ? O3A C2A C3A 124.6(17) . . ? C3A C2A C1A 119.4(17) . . ? C2A C3A H3A 121.1 . . ? C2A C3A C4A 117.8(10) . . ? C4A C3A H3A 121.1 . . ? O4A C4A C3A 115.2(5) . . ? O4A C4A C5A 123.4(5) . . ? C5A C4A C3A 121.4(5) . . ? C4A C5A H5A 120.3 . . ? C4A C5A C6A 119.4(6) . . ? C6A C5A H5A 120.3 . . ? C1A C6A C5A 118.5(7) . . ? C1A C6A H6A 120.7 . . ? C5A C6A H6A 120.7 . . ? O4A C10A H10A 109.5 . . ? O4A C10A H10B 109.5 . . ? O4A C10A H10C 109.5 . . ? H10A C10A H10B 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C8B O3B C2B 103(2) . . ? C4B O4B C7B 118.1(8) . . ? C7 C1B C6B 132.3(10) . . ? C2B C1B C7 117(2) . . ? C2B C1B C6B 111(3) . . ? C1B C2B O3B 108(4) . . ? C1B C2B C3B 136(4) . . ? C3B C2B O3B 115(4) . . ? C2B C3B H3B 125.2 . . ? C4B C3B C2B 110(2) . . ? C4B C3B H3B 125.1 . . ? O4B C4B C5B 114.5(12) . . ? C3B C4B O4B 120.7(10) . . ? C3B C4B C5B 124.8(12) . . ? C4B C5B H5B 120.0 . . ? C4B C5B C6B 120.1(13) . . ? C6B C5B H5B 120.0 . . ? C1B C6B H6B 120.8 . . ? C5B C6B C1B 118.3(12) . . ? C5B C6B H6B 120.8 . . ? O4B C7B H7BA 109.5 . . ? O4B C7B H7BB 109.5 . . ? O4B C7B H7BC 109.5 . . ? H7BA C7B H7BB 109.5 . . ? H7BA C7B H7BC 109.5 . . ? H7BB C7B H7BC 109.5 . . ? O3C C8C H8CA 108.0 . . ? O3C C8C H8CB 108.1 . . ? O3C C8C C7C 117(4) . . ? H8CA C8C H8CB 107.3 . . ? C7C C8C H8CA 108.0 . . ? C7C C8C H8CB 108.1 . . ? C9B C7C C11 107(3) . . ? C9B C7C C8C 108(4) . . ? C8C C7C C11 128(4) . . ? N C9 C7 111.3(3) . . ? N C9 H9A 109.4 . . ? N C9 H9B 109.4 . . ? C7 C9 H9A 109.4 . . ? C7 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C7 C8A H8AA 110.7 . . ? C7 C8A H8AB 110.7 . . ? O3A C8A C7 105.4(5) . . ? O3A C8A H8AA 110.7 . . ? O3A C8A H8AB 110.7 . . ? H8AA C8A H8AB 108.8 . . ? 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 S O1 1.4387(19) . ? S O2 1.4285(19) . ? S N 1.608(2) . ? S C18 1.762(3) . ? N H 0.80(3) . ? N C9B 1.47(2) . ? N C9 1.465(3) . ? C7 C8B 1.550(8) . ? C7 C11 1.540(4) . ? C7 C1A 1.552(6) . ? C7 C1B 1.430(12) . ? C7 C9 1.533(4) . ? C7 C8A 1.528(5) . ? C8B H8BA 0.9700 . ? C8B H8BB 0.9700 . ? C8B O3B 1.453(14) . ? C9B H9BA 0.9701 . ? C9B H9BB 0.9699 . ? C9B C7C 1.53(2) . ? C11 C12 1.383(4) . ? C11 C16 1.384(4) . ? C11 C7C 1.67(5) . ? C12 H12 0.9300 . ? C12 C13 1.371(4) . ? C13 H13 0.9297 . ? C13 C14 1.387(4) . ? C14 C15 1.377(4) . ? C14 C17 1.507(4) . ? C15 H15 0.9301 . ? C15 C16 1.387(4) . ? C16 H16 0.9300 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.373(4) . ? C18 C23 1.384(4) . ? C19 H19 0.9300 . ? C19 C20 1.381(4) . ? C20 H20 0.9300 . ? C20 C21 1.383(4) . ? C21 C22 1.381(4) . ? C21 C24 1.511(4) . ? C22 H22 0.9301 . ? C22 C23 1.374(4) . ? C23 H23 0.9300 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? O3A C2A 1.34(3) . ? O3A C8A 1.467(6) . ? O4A C4A 1.378(6) . ? O4A C10A 1.435(5) . ? C1A C2A 1.40(2) . ? C1A C6A 1.326(9) . ? C2A C3A 1.38(2) . ? C3A H3A 0.9300 . ? C3A C4A 1.392(7) . ? C4A C5A 1.387(6) . ? C5A H5A 0.9301 . ? C5A C6A 1.404(10) . ? C6A H6A 0.9300 . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? O3B C2B 1.48(6) . ? O4B C4B 1.382(13) . ? O4B C7B 1.439(11) . ? C1B C2B 1.31(5) . ? C1B C6B 1.51(2) . ? C2B C3B 1.40(5) . ? C3B H3B 0.9299 . ? C3B C4B 1.370(17) . ? C4B C5B 1.383(15) . ? C5B H5B 0.9300 . ? C5B C6B 1.42(2) . ? C6B H6B 0.9300 . ? C7B H7BA 0.9800 . ? C7B H7BB 0.9800 . ? C7B H7BC 0.9800 . ? O3C C8C 1.38(2) . ? C8C H8CA 0.9700 . ? C8C H8CB 0.9701 . ? C8C C7C 1.55(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C8A H8AA 0.9698 . ? C8A H8AB 0.9700 . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N H O1 0.80(3) 2.12(3) 2.919(3) 172(3) 3_766 yes 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 S N C9B C7C 180(4) . . . . ? S N C9 C7 126.0(3) . . . . ? S C18 C19 C20 -178.1(2) . . . . ? S C18 C23 C22 178.2(2) . . . . ? O1 S N C9B -161(4) . . . . ? O1 S N C9 -177.2(2) . . . . ? O1 S C18 C19 138.1(2) . . . . ? O1 S C18 C23 -40.9(2) . . . . ? O2 S N C9B -33(4) . . . . ? O2 S N C9 -49.3(3) . . . . ? O2 S C18 C19 8.7(2) . . . . ? O2 S C18 C23 -170.3(2) . . . . ? N S C18 C19 -108.2(2) . . . . ? N S C18 C23 72.8(2) . . . . ? N C9B C7C C11 -170(4) . . . . ? N C9B C7C C8C 49(7) . . . . ? C7 C8B O3B C2B -21(2) . . . . ? C7 C11 C12 C13 176.6(3) . . . . ? C7 C11 C16 C15 -176.2(3) . . . . ? C7 C11 C7C C9B 63(5) . . . . ? C7 C11 C7C C8C -167(8) . . . . ? C7 C1A C2A O3A 1.4(13) . . . . ? C7 C1A C2A C3A -172.6(10) . . . . ? C7 C1A C6A C5A 176.5(5) . . . . ? C7 C1B C2B O3B 10(3) . . . . ? C7 C1B C2B C3B -179(3) . . . . ? C7 C1B C6B C5B 173.5(11) . . . . ? C8B C7 C11 C12 -63.7(7) . . . . ? C8B C7 C11 C16 111.9(7) . . . . ? C8B C7 C1B C2B -22(2) . . . . ? C8B C7 C1B C6B 166.8(15) . . . . ? C8B O3B C2B C1B 8(3) . . . . ? C8B O3B C2B C3B -165(2) . . . . ? C11 C7 C8B O3B -90.1(16) . . . . ? C11 C7 C1A C2A 101.8(8) . . . . ? C11 C7 C1A C6A -78.2(7) . . . . ? C11 C7 C1B C2B 90(2) . . . . ? C11 C7 C1B C6B -81.3(13) . . . . ? C11 C7 C9 N 175.4(2) . . . . ? C11 C7 C8A O3A -92.8(6) . . . . ? C11 C12 C13 C14 0.0(5) . . . . ? C12 C11 C16 C15 -0.5(4) . . . . ? C12 C11 C7C C9B -30(5) . . . . ? C12 C11 C7C C8C 100(5) . . . . ? C12 C13 C14 C15 -1.0(4) . . . . ? C12 C13 C14 C17 -179.1(3) . . . . ? C13 C14 C15 C16 1.3(5) . . . . ? C14 C15 C16 C11 -0.5(5) . . . . ? C16 C11 C12 C13 0.8(4) . . . . ? C16 C11 C7C C9B 180(4) . . . . ? C16 C11 C7C C8C -50(5) . . . . ? C17 C14 C15 C16 179.4(3) . . . . ? C18 S N C9B 84(4) . . . . ? C18 S N C9 67.5(3) . . . . ? C18 C19 C20 C21 0.5(4) . . . . ? C19 C18 C23 C22 -0.8(4) . . . . ? C19 C20 C21 C22 -2.0(4) . . . . ? C19 C20 C21 C24 176.7(3) . . . . ? C20 C21 C22 C23 2.2(4) . . . . ? C21 C22 C23 C18 -0.8(4) . . . . ? C23 C18 C19 C20 0.9(4) . . . . ? C24 C21 C22 C23 -176.6(3) . . . . ? O3A C2A C3A C4A 179.8(11) . . . . ? O4A C4A C5A C6A 179.7(5) . . . . ? C1A C7 C11 C12 178.5(3) . . . . ? C1A C7 C11 C16 -5.9(4) . . . . ? C1A C7 C9 N 52.1(4) . . . . ? C1A C7 C8A O3A 26.5(7) . . . . ? C1A C2A C3A C4A -6.8(16) . . . . ? C2A O3A C8A C7 -26.7(11) . . . . ? C2A C1A C6A C5A -3.4(12) . . . . ? C2A C3A C4A O4A -176.0(9) . . . . ? C2A C3A C4A C5A 2.9(11) . . . . ? C3A C4A C5A C6A 0.9(8) . . . . ? C4A C5A C6A C1A -0.7(9) . . . . ? C6A C1A C2A O3A -178.7(9) . . . . ? C6A C1A C2A C3A 7.4(17) . . . . ? C10A O4A C4A C3A 172.9(4) . . . . ? C10A O4A C4A C5A -6.0(6) . . . . ? O3B C2B C3B C4B 179(2) . . . . ? O4B C4B C5B C6B -175.5(12) . . . . ? C1B C7 C8B O3B 24.9(17) . . . . ? C1B C7 C11 C12 -168.9(5) . . . . ? C1B C7 C11 C16 6.7(6) . . . . ? C1B C2B C3B C4B 9(5) . . . . ? C2B C1B C6B C5B 2(2) . . . . ? C2B C3B C4B O4B 173.3(18) . . . . ? C2B C3B C4B C5B -8(2) . . . . ? C3B C4B C5B C6B 6(2) . . . . ? C4B C5B C6B C1B -2(2) . . . . ? C6B C1B C2B O3B -176.4(19) . . . . ? C6B C1B C2B C3B -6(5) . . . . ? C7B O4B C4B C3B -8.2(14) . . . . ? C7B O4B C4B C5B 173.0(9) . . . . ? O3C C8C C7C C9B -140(5) . . . . ? O3C C8C C7C C11 91(6) . . . . ? C7C C11 C12 C13 -148(2) . . . . ? C7C C11 C16 C15 151(2) . . . . ? C9 C7 C11 C12 56.3(4) . . . . ? C9 C7 C11 C16 -128.1(3) . . . . ? C9 C7 C1A C2A -136.8(8) . . . . ? C9 C7 C1A C6A 43.3(7) . . . . ? C9 C7 C8A O3A 144.2(5) . . . . ? C8A C7 C11 C12 -68.8(4) . . . . ? C8A C7 C11 C16 106.7(4) . . . . ? C8A C7 C1A C2A -17.3(9) . . . . ? C8A C7 C1A C6A 162.8(7) . . . . ? C8A C7 C9 N -60.1(5) . . . . ? C8A O3A C2A C1A 16.1(14) . . . . ? C8A O3A C2A C3A -170.2(13) . . . . ?