#------------------------------------------------------------------------------ #$Date: 2020-05-13 02:18:16 +0300 (Wed, 13 May 2020) $ #$Revision: 251994 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038349.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_4038349 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 H30 N2 O3 S' _chemical_formula_sum 'C24 H30 N2 O3 S' _chemical_formula_weight 426.56 _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 _atom_sites_solution_secondary difmap _audit_creation_date 2019-11-07 _audit_creation_method ; Olex2 1.3-alpha (compiled 2019.10.31 svn.r3677 for OlexSys, GUI svn.r5972) ; _cell_angle_alpha 90 _cell_angle_beta 116.908(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.5538(7) _cell_length_b 21.7626(14) _cell_length_c 10.9319(7) _cell_measurement_reflns_used 9941 _cell_measurement_temperature 273.15 _cell_measurement_theta_max 30.89 _cell_measurement_theta_min 2.29 _cell_volume 2239.0(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 (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 '\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 0.0418 _diffrn_reflns_av_unetI/netI 0.0287 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 49376 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 29.995 _diffrn_reflns_theta_max 29.995 _diffrn_reflns_theta_min 2.226 _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 0.172 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9711 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker, 2016) was used for absorption correction. wR2(int) was 0.0899 before and 0.0460 after correction. The Ratio of minimum to maximum transmission is 0.9711. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.265 _exptl_crystal_description block _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.318 _exptl_crystal_size_mid 0.237 _exptl_crystal_size_min 0.17 _refine_diff_density_max 0.377 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.050 _refine_ls_extinction_coef 0.0036(10) _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 1.039 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 284 _refine_ls_number_reflns 6522 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.039 _refine_ls_R_factor_all 0.0572 _refine_ls_R_factor_gt 0.0399 _refine_ls_shift/su_max 0.008 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0570P)^2^+0.6728P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1014 _refine_ls_wR_factor_ref 0.1099 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5084 _reflns_number_total 6522 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 19srv332.cif _cod_data_source_block 19srv332 _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 4038349 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Others Uiso(H17A)=Uiso(H17B)=Uiso(H17C)=FVAR(1) Uiso(H24A)=Uiso(H24B)=Uiso(H24C)=FVAR(2) 3.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B) 3.b Aromatic/amide H refined with riding coordinates: C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23) 3.c Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C24(H24A,H24B,H24C) ; _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 0.947 _shelx_estimated_absorpt_t_max 0.971 _shelx_res_checksum 76005 _shelx_res_file ; TITL 19srv332_a.res in P2(1)/n 19srv332.res created by SHELXL-2018/3 at 17:04:00 on 07-Nov-2019 REM Old TITL 19srv332 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.136, Rweak 0.005, Alpha 0.032 REM 0.821 for 138 systematic absences, Orientation as input REM Formula found by SHELXT: C24 N3 O2 S CELL 0.71073 10.5538 21.7626 10.9319 90 116.908 90 ZERR 4 0.0007 0.0014 0.0007 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O S UNIT 96 120 8 12 4 L.S. 7 PLAN 5 SIZE 0.17 0.237 0.318 TEMP -153.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta 60 OMIT -3 60 REM REM REM WGHT 0.057000 0.672800 EXTI 0.003558 FVAR 0.66307 0.11616 0.05515 S 5 0.265027 0.494730 0.728747 11.00000 0.01495 0.02198 = 0.01986 0.00223 0.00870 0.00102 O1 4 0.115319 0.483030 0.665087 11.00000 0.01624 0.03279 = 0.03204 0.00305 0.01167 -0.00083 O2 4 0.350758 0.477522 0.869121 11.00000 0.02494 0.03271 = 0.01986 0.00472 0.01088 0.00237 O3 4 0.396042 0.305467 0.735647 11.00000 0.02553 0.02407 = 0.03973 0.00733 0.00674 -0.00769 N1 3 0.330621 0.459091 0.637140 11.00000 0.01414 0.01964 = 0.01676 0.00173 0.00586 0.00196 N2 3 0.499017 0.349683 0.615991 11.00000 0.01867 0.01714 = 0.02536 -0.00275 0.00269 0.00107 C1 1 0.487312 0.453622 0.702127 11.00000 0.01415 0.01652 = 0.02196 0.00241 0.00761 0.00065 AFIX 23 H1A 2 0.527458 0.479187 0.786124 11.00000 -1.20000 H1B 2 0.521551 0.470769 0.638555 11.00000 -1.20000 AFIX 0 C2 1 0.546125 0.387468 0.741270 11.00000 0.01518 0.01641 = 0.02069 0.00167 0.00598 0.00089 C3 1 0.486777 0.352545 0.827579 11.00000 0.01879 0.02096 = 0.02948 0.00755 0.00829 -0.00026 H3A 2 0.558513 0.331846 0.904487 11.00000 0.02817 H3B 2 0.428446 0.378013 0.855194 11.00000 0.02056 C4 1 0.418265 0.308148 0.622582 11.00000 0.02191 0.01769 = 0.03232 0.00431 0.00030 0.00113 C5 1 0.343327 0.259661 0.516870 11.00000 0.03663 0.01789 = 0.04546 -0.00066 -0.00519 -0.00487 AFIX 23 H5A 2 0.259886 0.245119 0.527352 11.00000 -1.20000 H5B 2 0.408185 0.224278 0.534158 11.00000 -1.20000 AFIX 0 C6 1 0.293595 0.281541 0.369712 11.00000 0.03145 0.02375 = 0.04038 -0.01191 0.00716 -0.00254 AFIX 23 H6A 2 0.368267 0.307897 0.366063 11.00000 -1.20000 H6B 2 0.281392 0.245390 0.310422 11.00000 -1.20000 AFIX 0 C7 1 0.154716 0.317375 0.312706 11.00000 0.02638 0.02777 = 0.02680 -0.00374 0.00402 -0.00641 AFIX 23 H7A 2 0.078953 0.289605 0.309451 11.00000 -1.20000 H7B 2 0.129810 0.329426 0.217172 11.00000 -1.20000 AFIX 0 C8 1 0.154712 0.375140 0.392319 11.00000 0.01838 0.02904 = 0.02344 -0.00064 0.00499 -0.00118 AFIX 23 H8A 2 0.056725 0.391628 0.352314 11.00000 -1.20000 H8B 2 0.181159 0.363255 0.488272 11.00000 -1.20000 AFIX 0 C9 1 0.254038 0.426325 0.393990 11.00000 0.02256 0.02330 = 0.01799 -0.00017 0.00678 0.00078 AFIX 23 H9A 2 0.350343 0.409221 0.423098 11.00000 -1.20000 H9B 2 0.220050 0.442902 0.300045 11.00000 -1.20000 AFIX 0 C10 1 0.261985 0.478034 0.490235 11.00000 0.02239 0.02119 = 0.01693 0.00335 0.00619 0.00380 AFIX 23 H10A 2 0.316222 0.512626 0.478171 11.00000 -1.20000 H10B 2 0.164642 0.492869 0.465208 11.00000 -1.20000 AFIX 0 C11 1 0.290665 0.573759 0.714449 11.00000 0.02180 0.02075 = 0.02565 -0.00099 0.01443 0.00111 C12 1 0.188317 0.607390 0.606887 11.00000 0.02719 0.02677 = 0.03088 0.00292 0.01556 0.00645 AFIX 43 H12 2 0.102564 0.588438 0.543377 11.00000 -1.20000 AFIX 0 C13 1 0.213388 0.668936 0.593834 11.00000 0.04321 0.02667 = 0.04620 0.00960 0.02732 0.01165 AFIX 43 H13 2 0.143417 0.692293 0.521295 11.00000 -1.20000 AFIX 0 C14 1 0.339168 0.697176 0.685011 11.00000 0.04813 0.02227 = 0.06767 0.00205 0.04087 0.00206 C15 1 0.439278 0.662698 0.791909 11.00000 0.03429 0.02884 = 0.05565 -0.01126 0.02421 -0.00795 AFIX 43 H15 2 0.525032 0.681696 0.855288 11.00000 -1.20000 AFIX 0 C16 1 0.416734 0.601189 0.808073 11.00000 0.02517 0.02812 = 0.03266 -0.00599 0.01361 -0.00146 AFIX 43 H16 2 0.486016 0.578096 0.881712 11.00000 -1.20000 AFIX 0 C17 1 0.364999 0.764151 0.667551 11.00000 0.07009 0.02587 = 0.11678 0.00654 0.05847 -0.00114 AFIX 137 H17A 2 0.339084 0.772343 0.570948 11.00000 21.00000 H17B 2 0.465691 0.773790 0.723947 11.00000 21.00000 H17C 2 0.306978 0.789767 0.696431 11.00000 21.00000 AFIX 0 C18 1 0.706576 0.394090 0.812273 11.00000 0.01389 0.01456 = 0.02118 0.00174 0.00608 0.00138 C19 1 0.777828 0.410574 0.950333 11.00000 0.01820 0.02595 = 0.02261 -0.00193 0.00990 0.00024 AFIX 43 H19 2 0.725725 0.416181 1.001158 11.00000 -1.20000 AFIX 0 C20 1 0.923816 0.418865 1.014175 11.00000 0.01870 0.02607 = 0.02077 -0.00136 0.00520 -0.00165 AFIX 43 H20 2 0.970391 0.429879 1.108439 11.00000 -1.20000 AFIX 0 C21 1 1.003578 0.411345 0.942669 11.00000 0.01589 0.01871 = 0.02664 0.00548 0.00755 0.00080 C22 1 0.931196 0.396553 0.803945 11.00000 0.02075 0.02275 = 0.02552 0.00533 0.01306 0.00277 AFIX 43 H22 2 0.982876 0.392416 0.752332 11.00000 -1.20000 AFIX 0 C23 1 0.785285 0.387730 0.739519 11.00000 0.02048 0.01998 = 0.01908 0.00301 0.00774 0.00242 AFIX 43 H23 2 0.738606 0.377258 0.644947 11.00000 -1.20000 AFIX 0 C24 1 1.162954 0.418286 1.012486 11.00000 0.01670 0.03542 = 0.03281 0.00655 0.00834 -0.00286 AFIX 137 H24A 2 1.188651 0.457495 1.061849 11.00000 31.00000 H24B 2 1.198171 0.417431 0.943526 11.00000 31.00000 H24C 2 1.205649 0.384443 1.077469 11.00000 31.00000 AFIX 0 HKLF 4 REM 19srv332_a.res in P2(1)/n REM wR2 = 0.1099, GooF = S = 1.039, Restrained GooF = 1.039 for all data REM R1 = 0.0399 for 5084 Fo > 4sig(Fo) and 0.0572 for all 6522 data REM 284 parameters refined using 0 restraints END WGHT 0.0569 0.6574 REM Highest difference peak 0.377, deepest hole -0.438, 1-sigma level 0.050 Q1 1 0.7505 0.3840 0.7877 11.00000 0.05 0.38 Q2 1 0.2796 0.5409 0.7182 11.00000 0.05 0.36 Q3 1 0.3061 0.4763 0.6776 11.00000 0.05 0.35 Q4 1 0.8544 0.4088 0.9869 11.00000 0.05 0.32 Q5 1 0.8557 0.3922 0.7793 11.00000 0.05 0.32 ; _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 0.26503(3) 0.49473(2) 0.72875(3) 0.01862(8) Uani 1 1 d . . . . . O1 O 0.11532(10) 0.48303(5) 0.66509(10) 0.0267(2) Uani 1 1 d . . . . . O2 O 0.35076(10) 0.47752(5) 0.86912(9) 0.0256(2) Uani 1 1 d . . . . . O3 O 0.39604(10) 0.30547(5) 0.73565(11) 0.0328(2) Uani 1 1 d . . . . . N1 N 0.33062(10) 0.45909(5) 0.63714(10) 0.0173(2) Uani 1 1 d . . . . . N2 N 0.49902(11) 0.34968(5) 0.61599(11) 0.0232(2) Uani 1 1 d . . . . . C1 C 0.48731(12) 0.45362(5) 0.70213(12) 0.0178(2) Uani 1 1 d . . . . . H1A H 0.527458 0.479187 0.786124 0.021 Uiso 1 1 calc R U . . . H1B H 0.521551 0.470769 0.638555 0.021 Uiso 1 1 calc R U . . . C2 C 0.54613(12) 0.38747(5) 0.74127(12) 0.0182(2) Uani 1 1 d . . . . . C3 C 0.48678(14) 0.35254(6) 0.82758(14) 0.0241(3) Uani 1 1 d . . . . . H3A H 0.5585(17) 0.3318(8) 0.9045(16) 0.028(4) Uiso 1 1 d . . . . . H3B H 0.4284(16) 0.3780(7) 0.8552(15) 0.021(4) Uiso 1 1 d . . . . . C4 C 0.41826(14) 0.30815(6) 0.62258(14) 0.0285(3) Uani 1 1 d . . . . . C5 C 0.34333(18) 0.25966(7) 0.51687(17) 0.0423(4) Uani 1 1 d . . . . . H5A H 0.259886 0.245119 0.527352 0.051 Uiso 1 1 calc R U . . . H5B H 0.408185 0.224278 0.534158 0.051 Uiso 1 1 calc R U . . . C6 C 0.29360(16) 0.28154(7) 0.36971(16) 0.0353(3) Uani 1 1 d . . . . . H6A H 0.368267 0.307897 0.366063 0.042 Uiso 1 1 calc R U . . . H6B H 0.281392 0.245390 0.310422 0.042 Uiso 1 1 calc R U . . . C7 C 0.15472(15) 0.31738(7) 0.31271(14) 0.0300(3) Uani 1 1 d . . . . . H7A H 0.078953 0.289605 0.309451 0.036 Uiso 1 1 calc R U . . . H7B H 0.129810 0.329426 0.217172 0.036 Uiso 1 1 calc R U . . . C8 C 0.15471(14) 0.37514(6) 0.39232(14) 0.0253(3) Uani 1 1 d . . . . . H8A H 0.056725 0.391628 0.352314 0.030 Uiso 1 1 calc R U . . . H8B H 0.181159 0.363255 0.488272 0.030 Uiso 1 1 calc R U . . . C9 C 0.25404(14) 0.42632(6) 0.39399(13) 0.0222(2) Uani 1 1 d . . . . . H9A H 0.350343 0.409221 0.423098 0.027 Uiso 1 1 calc R U . . . H9B H 0.220050 0.442902 0.300045 0.027 Uiso 1 1 calc R U . . . C10 C 0.26198(14) 0.47803(6) 0.49024(12) 0.0212(2) Uani 1 1 d . . . . . H10A H 0.316222 0.512626 0.478171 0.025 Uiso 1 1 calc R U . . . H10B H 0.164642 0.492869 0.465208 0.025 Uiso 1 1 calc R U . . . C11 C 0.29067(13) 0.57376(6) 0.71445(13) 0.0213(2) Uani 1 1 d . . . . . C12 C 0.18832(15) 0.60739(6) 0.60689(15) 0.0274(3) Uani 1 1 d . . . . . H12 H 0.102564 0.588438 0.543377 0.033 Uiso 1 1 calc R U . . . C13 C 0.21339(18) 0.66894(7) 0.59383(17) 0.0360(3) Uani 1 1 d . . . . . H13 H 0.143417 0.692293 0.521295 0.043 Uiso 1 1 calc R U . . . C14 C 0.33917(19) 0.69718(7) 0.6850(2) 0.0405(4) Uani 1 1 d . . . . . C15 C 0.43928(17) 0.66270(7) 0.79191(19) 0.0381(4) Uani 1 1 d . . . . . H15 H 0.525032 0.681696 0.855288 0.046 Uiso 1 1 calc R U . . . C16 C 0.41673(15) 0.60119(6) 0.80807(15) 0.0285(3) Uani 1 1 d . . . . . H16 H 0.486016 0.578096 0.881712 0.034 Uiso 1 1 calc R U . . . C17 C 0.3650(2) 0.76415(8) 0.6676(3) 0.0648(6) Uani 1 1 d . . . . . H17A H 0.339084 0.772343 0.570948 0.116(6) Uiso 1 1 calc R U . . . H17B H 0.465691 0.773790 0.723947 0.116(6) Uiso 1 1 calc R U . . . H17C H 0.306978 0.789767 0.696431 0.116(6) Uiso 1 1 calc R U . . . C18 C 0.70658(12) 0.39409(5) 0.81227(12) 0.0172(2) Uani 1 1 d . . . . . C19 C 0.77783(13) 0.41057(6) 0.95033(13) 0.0220(2) Uani 1 1 d . . . . . H19 H 0.725725 0.416181 1.001158 0.026 Uiso 1 1 calc R U . . . C20 C 0.92382(13) 0.41886(6) 1.01418(13) 0.0233(3) Uani 1 1 d . . . . . H20 H 0.970391 0.429879 1.108439 0.028 Uiso 1 1 calc R U . . . C21 C 1.00358(13) 0.41135(6) 0.94267(13) 0.0212(2) Uani 1 1 d . . . . . C22 C 0.93120(13) 0.39655(6) 0.80395(13) 0.0220(2) Uani 1 1 d . . . . . H22 H 0.982876 0.392416 0.752332 0.026 Uiso 1 1 calc R U . . . C23 C 0.78528(13) 0.38773(6) 0.73952(12) 0.0203(2) Uani 1 1 d . . . . . H23 H 0.738606 0.377258 0.644947 0.024 Uiso 1 1 calc R U . . . C24 C 1.16295(13) 0.41829(7) 1.01249(15) 0.0294(3) Uani 1 1 d . . . . . H24A H 1.188651 0.457495 1.061849 0.055(3) Uiso 1 1 calc R U . . . H24B H 1.198171 0.417431 0.943526 0.055(3) Uiso 1 1 calc R U . . . H24C H 1.205649 0.384443 1.077469 0.055(3) 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 S 0.01495(14) 0.02198(15) 0.01986(15) 0.00223(11) 0.00870(11) 0.00102(11) O1 0.0162(4) 0.0328(5) 0.0320(5) 0.0030(4) 0.0117(4) -0.0008(4) O2 0.0249(5) 0.0327(5) 0.0199(4) 0.0047(4) 0.0109(4) 0.0024(4) O3 0.0255(5) 0.0241(5) 0.0397(6) 0.0073(4) 0.0067(4) -0.0077(4) N1 0.0141(5) 0.0196(5) 0.0168(5) 0.0017(4) 0.0059(4) 0.0020(4) N2 0.0187(5) 0.0171(5) 0.0254(5) -0.0028(4) 0.0027(4) 0.0011(4) C1 0.0142(5) 0.0165(5) 0.0220(6) 0.0024(4) 0.0076(4) 0.0006(4) C2 0.0152(5) 0.0164(5) 0.0207(6) 0.0017(4) 0.0060(4) 0.0009(4) C3 0.0188(6) 0.0210(6) 0.0295(7) 0.0076(5) 0.0083(5) -0.0003(5) C4 0.0219(6) 0.0177(6) 0.0323(7) 0.0043(5) 0.0003(5) 0.0011(5) C5 0.0366(8) 0.0179(6) 0.0455(9) -0.0007(6) -0.0052(7) -0.0049(6) C6 0.0314(8) 0.0238(7) 0.0404(8) -0.0119(6) 0.0072(6) -0.0025(6) C7 0.0264(7) 0.0278(7) 0.0268(7) -0.0037(5) 0.0040(5) -0.0064(5) C8 0.0184(6) 0.0290(7) 0.0234(6) -0.0006(5) 0.0050(5) -0.0012(5) C9 0.0226(6) 0.0233(6) 0.0180(5) -0.0002(4) 0.0068(5) 0.0008(5) C10 0.0224(6) 0.0212(6) 0.0169(5) 0.0034(4) 0.0062(5) 0.0038(5) C11 0.0218(6) 0.0208(6) 0.0257(6) -0.0010(5) 0.0144(5) 0.0011(5) C12 0.0272(7) 0.0268(7) 0.0309(7) 0.0029(5) 0.0156(6) 0.0064(5) C13 0.0432(9) 0.0267(7) 0.0462(9) 0.0096(6) 0.0273(7) 0.0117(6) C14 0.0481(10) 0.0223(7) 0.0677(11) 0.0021(7) 0.0409(9) 0.0021(6) C15 0.0343(8) 0.0288(7) 0.0557(10) -0.0113(7) 0.0242(7) -0.0079(6) C16 0.0252(7) 0.0281(7) 0.0327(7) -0.0060(5) 0.0136(6) -0.0015(5) C17 0.0701(14) 0.0259(8) 0.117(2) 0.0065(10) 0.0585(14) -0.0011(9) C18 0.0139(5) 0.0146(5) 0.0212(6) 0.0017(4) 0.0061(4) 0.0014(4) C19 0.0182(6) 0.0259(6) 0.0226(6) -0.0019(5) 0.0099(5) 0.0002(5) C20 0.0187(6) 0.0261(6) 0.0208(6) -0.0014(5) 0.0052(5) -0.0016(5) C21 0.0159(5) 0.0187(6) 0.0266(6) 0.0055(5) 0.0076(5) 0.0008(4) C22 0.0207(6) 0.0228(6) 0.0255(6) 0.0053(5) 0.0131(5) 0.0028(5) C23 0.0205(6) 0.0200(6) 0.0191(6) 0.0030(4) 0.0077(5) 0.0024(4) C24 0.0167(6) 0.0354(7) 0.0328(7) 0.0065(6) 0.0083(5) -0.0029(5) 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 1.00 1.00 0.1280 0.00 -1.00 -1.00 0.1040 1.00 -2.00 -1.00 0.0730 -1.00 2.00 1.00 0.1170 -1.00 2.00 2.00 0.1200 1.00 -2.00 1.00 0.1440 -1.00 2.00 -1.00 0.1350 0.00 0.00 -1.00 0.1110 -1.00 0.00 2.00 0.1150 0.00 -1.00 1.00 0.1370 1.00 0.00 -2.00 0.0960 -1.00 0.00 1.00 0.1150 -1.00 -2.00 2.00 0.0980 0.00 2.00 -1.00 0.1070 2.00 1.00 -2.00 0.0630 0.00 1.00 0.00 0.0850 0.00 -1.00 0.00 0.0840 1.00 2.00 0.00 0.1020 -1.00 -2.00 0.00 0.1060 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 O2 119.78(6) . . ? O1 S N1 107.21(6) . . ? O1 S C11 108.12(6) . . ? O2 S N1 107.01(5) . . ? O2 S C11 107.60(6) . . ? N1 S C11 106.42(5) . . ? C4 O3 C3 105.55(10) . . ? C1 N1 S 115.59(8) . . ? C1 N1 C10 115.60(9) . . ? C10 N1 S 113.08(8) . . ? C4 N2 C2 107.30(11) . . ? N1 C1 H1A 108.4 . . ? N1 C1 H1B 108.4 . . ? N1 C1 C2 115.36(9) . . ? H1A C1 H1B 107.5 . . ? C2 C1 H1A 108.4 . . ? C2 C1 H1B 108.4 . . ? N2 C2 C1 109.66(9) . . ? N2 C2 C3 103.45(10) . . ? N2 C2 C18 110.89(10) . . ? C3 C2 C1 113.74(10) . . ? C18 C2 C1 105.54(9) . . ? C18 C2 C3 113.63(10) . . ? O3 C3 C2 104.29(10) . . ? O3 C3 H3A 106.8(10) . . ? O3 C3 H3B 107.8(9) . . ? C2 C3 H3A 113.0(10) . . ? C2 C3 H3B 113.4(9) . . ? H3A C3 H3B 111.0(13) . . ? O3 C4 C5 115.01(13) . . ? N2 C4 O3 118.67(12) . . ? N2 C4 C5 126.32(15) . . ? C4 C5 H5A 108.8 . . ? C4 C5 H5B 108.8 . . ? C4 C5 C6 113.77(12) . . ? H5A C5 H5B 107.7 . . ? C6 C5 H5A 108.8 . . ? C6 C5 H5B 108.8 . . ? C5 C6 H6A 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C7 C6 C5 113.56(14) . . ? C7 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C6 C7 H7A 108.3 . . ? C6 C7 H7B 108.3 . . ? C6 C7 C8 115.86(11) . . ? H7A C7 H7B 107.4 . . ? C8 C7 H7A 108.3 . . ? C8 C7 H7B 108.3 . . ? C7 C8 H8A 108.4 . . ? C7 C8 H8B 108.4 . . ? H8A C8 H8B 107.5 . . ? C9 C8 C7 115.50(11) . . ? C9 C8 H8A 108.4 . . ? C9 C8 H8B 108.4 . . ? C8 C9 H9A 109.2 . . ? C8 C9 H9B 109.2 . . ? H9A C9 H9B 107.9 . . ? C10 C9 C8 111.86(11) . . ? C10 C9 H9A 109.2 . . ? C10 C9 H9B 109.2 . . ? N1 C10 C9 112.93(10) . . ? N1 C10 H10A 109.0 . . ? N1 C10 H10B 109.0 . . ? C9 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C12 C11 S 119.85(10) . . ? C12 C11 C16 120.90(13) . . ? C16 C11 S 119.19(10) . . ? C11 C12 H12 120.5 . . ? C13 C12 C11 118.97(14) . . ? C13 C12 H12 120.5 . . ? C12 C13 H13 119.4 . . ? C12 C13 C14 121.21(15) . . ? C14 C13 H13 119.4 . . ? C13 C14 C17 120.26(17) . . ? C15 C14 C13 118.70(14) . . ? C15 C14 C17 121.04(18) . . ? C14 C15 H15 119.3 . . ? C16 C15 C14 121.37(15) . . ? C16 C15 H15 119.3 . . ? C11 C16 H16 120.6 . . ? C15 C16 C11 118.85(14) . . ? C15 C16 H16 120.6 . . ? 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 C2 120.57(11) . . ? C23 C18 C2 120.97(11) . . ? C23 C18 C19 118.34(11) . . ? C18 C19 H19 119.6 . . ? C20 C19 C18 120.71(12) . . ? C20 C19 H19 119.6 . . ? C19 C20 H20 119.4 . . ? C19 C20 C21 121.23(12) . . ? C21 C20 H20 119.4 . . ? C20 C21 C24 121.54(12) . . ? C22 C21 C20 117.72(11) . . ? C22 C21 C24 120.74(12) . . ? C21 C22 H22 119.3 . . ? C23 C22 C21 121.40(12) . . ? C23 C22 H22 119.3 . . ? C18 C23 H23 119.7 . . ? C22 C23 C18 120.56(11) . . ? C22 C23 H23 119.7 . . ? 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 . . ? 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 1.4319(10) . ? S O2 1.4342(9) . ? S N1 1.6466(10) . ? S C11 1.7590(13) . ? O3 C3 1.4511(17) . ? O3 C4 1.3596(19) . ? N1 C1 1.4799(15) . ? N1 C10 1.4902(15) . ? N2 C2 1.4774(16) . ? N2 C4 1.2665(17) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.5494(16) . ? C2 C3 1.5476(17) . ? C2 C18 1.5169(16) . ? C3 H3A 0.952(16) . ? C3 H3B 0.972(15) . ? C4 C5 1.499(2) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.525(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.523(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.5290(19) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.5240(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.5168(18) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.3912(19) . ? C11 C16 1.3934(19) . ? C12 H12 0.9500 . ? C12 C13 1.385(2) . ? C13 H13 0.9500 . ? C13 C14 1.391(2) . ? C14 C15 1.388(2) . ? C14 C17 1.511(2) . ? C15 H15 0.9500 . ? C15 C16 1.385(2) . ? C16 H16 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.3946(17) . ? C18 C23 1.3927(17) . ? C19 H19 0.9500 . ? C19 C20 1.3857(17) . ? C20 H20 0.9500 . ? C20 C21 1.3936(18) . ? C21 C22 1.3923(18) . ? C21 C24 1.5075(17) . ? C22 H22 0.9500 . ? C22 C23 1.3866(17) . ? C23 H23 0.9500 . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 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 S N1 C1 C2 112.42(10) . . . . ? S N1 C10 C9 -147.20(9) . . . . ? S C11 C12 C13 -177.10(11) . . . . ? S C11 C16 C15 176.70(11) . . . . ? O1 S N1 C1 -166.79(8) . . . . ? O1 S N1 C10 56.75(9) . . . . ? O1 S C11 C12 -26.79(12) . . . . ? O1 S C11 C16 156.06(10) . . . . ? O2 S N1 C1 -37.12(9) . . . . ? O2 S N1 C10 -173.58(8) . . . . ? O2 S C11 C12 -157.48(10) . . . . ? O2 S C11 C16 25.36(12) . . . . ? O3 C4 C5 C6 145.48(14) . . . . ? N1 S C11 C12 88.10(11) . . . . ? N1 S C11 C16 -89.05(11) . . . . ? N1 C1 C2 N2 63.59(13) . . . . ? N1 C1 C2 C3 -51.68(14) . . . . ? N1 C1 C2 C18 -176.91(9) . . . . ? N2 C2 C3 O3 -8.50(12) . . . . ? N2 C2 C18 C19 -159.91(11) . . . . ? N2 C2 C18 C23 24.19(15) . . . . ? N2 C4 C5 C6 -35.2(2) . . . . ? C1 N1 C10 C9 76.35(13) . . . . ? C1 C2 C3 O3 110.39(11) . . . . ? C1 C2 C18 C19 81.40(13) . . . . ? C1 C2 C18 C23 -94.49(12) . . . . ? C2 N2 C4 O3 -1.84(15) . . . . ? C2 N2 C4 C5 178.89(13) . . . . ? C2 C18 C19 C20 -177.61(11) . . . . ? C2 C18 C23 C22 177.12(11) . . . . ? C3 O3 C4 N2 -4.04(16) . . . . ? C3 O3 C4 C5 175.31(11) . . . . ? C3 C2 C18 C19 -43.89(15) . . . . ? C3 C2 C18 C23 140.21(12) . . . . ? C4 O3 C3 C2 7.60(13) . . . . ? C4 N2 C2 C1 -115.21(11) . . . . ? C4 N2 C2 C3 6.46(13) . . . . ? C4 N2 C2 C18 128.62(11) . . . . ? C4 C5 C6 C7 -80.96(17) . . . . ? C5 C6 C7 C8 58.63(17) . . . . ? C6 C7 C8 C9 64.64(17) . . . . ? C7 C8 C9 C10 -172.40(11) . . . . ? C8 C9 C10 N1 66.70(14) . . . . ? C10 N1 C1 C2 -112.22(11) . . . . ? C11 S N1 C1 77.71(9) . . . . ? C11 S N1 C10 -58.75(9) . . . . ? C11 C12 C13 C14 0.8(2) . . . . ? C12 C11 C16 C15 -0.4(2) . . . . ? C12 C13 C14 C15 -1.1(2) . . . . ? C12 C13 C14 C17 179.15(16) . . . . ? C13 C14 C15 C16 0.7(2) . . . . ? C14 C15 C16 C11 0.1(2) . . . . ? C16 C11 C12 C13 0.0(2) . . . . ? C17 C14 C15 C16 -179.59(16) . . . . ? C18 C2 C3 O3 -128.82(10) . . . . ? C18 C19 C20 C21 0.3(2) . . . . ? C19 C18 C23 C22 1.13(18) . . . . ? C19 C20 C21 C22 1.41(19) . . . . ? C19 C20 C21 C24 -178.01(12) . . . . ? C20 C21 C22 C23 -1.90(18) . . . . ? C21 C22 C23 C18 0.64(19) . . . . ? C23 C18 C19 C20 -1.61(18) . . . . ? C24 C21 C22 C23 177.53(12) . . . . ?