#------------------------------------------------------------------------------ #$Date: 2020-05-13 02:17:09 +0300 (Wed, 13 May 2020) $ #$Revision: 251991 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038346.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_4038346 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 'C37 H40 N4 O6 S2' _chemical_formula_sum 'C37 H40 N4 O6 S2' _chemical_formula_weight 700.85 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2020-01-30 _audit_creation_method ; Olex2 1.3-alpha (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _cell_angle_alpha 90 _cell_angle_beta 94.212(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 15.0965(9) _cell_length_b 12.1682(7) _cell_length_c 21.8118(12) _cell_measurement_reflns_used 9891 _cell_measurement_temperature 120 _cell_measurement_theta_max 27.15 _cell_measurement_theta_min 2.31 _cell_volume 3995.9(4) _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 0.0435 _diffrn_reflns_av_unetI/netI 0.0288 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 36802 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 27.481 _diffrn_reflns_theta_max 27.481 _diffrn_reflns_theta_min 2.152 _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 0.179 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9394 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker, 2016) was used for absorption correction. wR2(int) was 0.0590 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.9394. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.165 _exptl_crystal_description block _exptl_crystal_F_000 1480 _exptl_crystal_size_max 0.401 _exptl_crystal_size_mid 0.365 _exptl_crystal_size_min 0.282 _refine_diff_density_max 0.293 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.044 _refine_ls_extinction_coef 0.0013(3) _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 1.027 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 4596 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0385 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0588P)^2^+1.9617P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0995 _refine_ls_wR_factor_ref 0.1092 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3412 _reflns_number_total 4596 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 20srv032.cif _cod_data_source_block 20srv032 _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 4038346 _smtbx_masks_void_probe_radius 1.2 _smtbx_masks_void_truncation_radius 1.2 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Others Uiso(H7A)=Uiso(H7B)=Uiso(H7C)=FVAR(1) Fixed Sof: H19A(0.5) H19B(0.5) 3.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C10(H10A,H10B), C18(H18A,H18B), C19(H19A,H19B) 3.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16) 3.c Idealised Me refined as rotating group: C7(H7A,H7B,H7C) ; _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 0.932 _shelx_estimated_absorpt_t_max 0.951 _shelx_res_checksum 19245 _shelx_res_file ; TITL 20srv032_a.res in C2/c 20srv032.res created by SHELXL-2018/3 at 21:40:13 on 30-Jan-2020 REM Old TITL 20srv032 in C2/c REM SHELXT solution in C2/c: R1 0.171, Rweak 0.005, Alpha 0.030 REM 0.510 for 201 systematic absences, Orientation as input REM Formula found by SHELXT: C20 N2 O3 S CELL 0.71073 15.0965 12.1682 21.8118 90 94.212 90 ZERR 4 0.0009 0.0007 0.0012 0 0.002 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O S UNIT 148 160 16 24 8 EQIV $1 1-X,+Y,1.5-Z L.S. 7 PLAN 8 SIZE 0.282 0.365 0.401 TEMP -153.15 CONF HTAB N1 N2_$1 BOND list 4 MORE -1 BOND $H ABIN fmap 2 53 acta 55 REM REM REM WGHT 0.058800 1.961700 EXTI 0.001307 FVAR 0.33523 0.06841 S 5 0.642680 0.497734 0.617654 11.00000 0.02699 0.04051 = 0.01674 -0.00089 0.00659 -0.00413 O1 4 0.590359 0.417329 0.583294 11.00000 0.04108 0.03706 = 0.02339 -0.00281 0.00424 -0.00620 O2 4 0.736621 0.483540 0.628731 11.00000 0.02841 0.05776 = 0.02636 0.00453 0.00955 0.00120 O3 4 0.670471 0.284978 0.781883 11.00000 0.02813 0.03756 = 0.03867 0.00483 0.01172 0.00836 N1 3 0.601269 0.504862 0.683284 11.00000 0.02368 0.04849 = 0.01639 -0.00063 0.00520 -0.00763 H1 2 0.548597 0.489435 0.680333 11.00000 0.03853 N2 3 0.581507 0.426142 0.804129 11.00000 0.02418 0.03438 = 0.01943 0.00371 0.00663 0.00242 C1 1 0.627388 0.624050 0.578378 11.00000 0.02787 0.03813 = 0.01627 -0.00352 0.00755 -0.00655 C2 1 0.555533 0.637463 0.535857 11.00000 0.02758 0.03711 = 0.02564 -0.00400 0.00381 -0.01081 AFIX 43 H2 2 0.512709 0.580617 0.529489 11.00000 -1.20000 AFIX 0 C3 1 0.546520 0.734188 0.502712 11.00000 0.03022 0.04083 = 0.02712 -0.00187 0.00195 -0.00597 AFIX 43 H3 2 0.497417 0.742708 0.473278 11.00000 -1.20000 AFIX 0 C4 1 0.607376 0.818937 0.511406 11.00000 0.03580 0.03826 = 0.02704 -0.00254 0.01015 -0.00656 C5 1 0.678428 0.804510 0.555257 11.00000 0.04179 0.04302 = 0.03649 -0.00220 0.00183 -0.02146 AFIX 43 H5 2 0.720273 0.862203 0.562566 11.00000 -1.20000 AFIX 0 C6 1 0.689099 0.708044 0.588223 11.00000 0.03344 0.05128 = 0.02505 -0.00234 -0.00118 -0.01438 AFIX 43 H6 2 0.738364 0.699126 0.617482 11.00000 -1.20000 AFIX 0 C7 1 0.598616 0.922990 0.473734 11.00000 0.04928 0.03972 = 0.04396 0.00322 0.00996 -0.00808 AFIX 137 H7A 2 0.648187 0.928080 0.447275 11.00000 21.00000 H7B 2 0.599560 0.986707 0.501255 11.00000 21.00000 H7C 2 0.542414 0.921717 0.448223 11.00000 21.00000 AFIX 0 C8 1 0.645177 0.559968 0.736164 11.00000 0.02751 0.03848 = 0.01751 0.00151 0.00398 -0.00248 AFIX 23 H8A 2 0.606633 0.619831 0.749599 11.00000 -1.20000 H8B 2 0.701263 0.593274 0.724315 11.00000 -1.20000 AFIX 0 C9 1 0.665666 0.479469 0.790011 11.00000 0.02282 0.03785 = 0.01813 0.00159 0.00631 0.00091 C10 1 0.724154 0.381521 0.772277 11.00000 0.02444 0.04275 = 0.02521 0.00021 0.00899 0.00259 AFIX 23 H10A 2 0.738410 0.386976 0.728797 11.00000 -1.20000 H10B 2 0.780276 0.379179 0.798747 11.00000 -1.20000 AFIX 0 C11 1 0.705978 0.542179 0.845322 11.00000 0.02455 0.03671 = 0.01827 0.00199 0.00476 0.00423 C12 1 0.784792 0.599530 0.841046 11.00000 0.03393 0.07014 = 0.02193 -0.00198 0.00916 -0.01112 AFIX 43 H12 2 0.812103 0.600159 0.803173 11.00000 -1.20000 AFIX 0 C13 1 0.824251 0.655779 0.890978 11.00000 0.03977 0.06289 = 0.03071 -0.00392 0.00518 -0.01472 AFIX 43 H13 2 0.878282 0.694396 0.887247 11.00000 -1.20000 AFIX 0 C14 1 0.785189 0.655788 0.946105 11.00000 0.04193 0.04155 = 0.02542 -0.00610 0.00244 0.00272 AFIX 43 H14 2 0.812188 0.694038 0.980558 11.00000 -1.20000 AFIX 0 C15 1 0.706470 0.599738 0.950864 11.00000 0.04482 0.04020 = 0.02138 -0.00115 0.01230 0.00471 AFIX 43 H15 2 0.679161 0.600002 0.988739 11.00000 -1.20000 AFIX 0 C16 1 0.666852 0.543081 0.900968 11.00000 0.03290 0.03395 = 0.02250 0.00233 0.00928 0.00435 AFIX 43 H16 2 0.612738 0.504736 0.904866 11.00000 -1.20000 AFIX 0 C17 1 0.591346 0.323558 0.798578 11.00000 0.02654 0.03941 = 0.02490 0.00806 0.00825 0.00665 C18 1 0.522694 0.238036 0.807646 11.00000 0.03471 0.03679 = 0.04803 0.01523 0.01729 0.00549 AFIX 23 H18A 2 0.468016 0.274336 0.819884 11.00000 -1.20000 H18B 2 0.544456 0.188819 0.841624 11.00000 -1.20000 AFIX 0 C19 1 0.500000 0.169084 0.750000 10.50000 0.03346 0.02919 = 0.07164 0.00000 0.02151 0.00000 AFIX 23 H19A 2 0.551172 0.121101 0.742807 10.50000 -1.20000 H19B 2 0.448829 0.121100 0.757193 10.50000 -1.20000 AFIX 0 HKLF 4 REM 20srv032_a.res in C2/c REM wR2 = 0.1092, GooF = S = 1.027, Restrained GooF = 1.027 for all data REM R1 = 0.0385 for 3412 Fo > 4sig(Fo) and 0.0586 for all 4596 data REM 229 parameters refined using 0 restraints END WGHT 0.0588 1.9618 REM Highest difference peak 0.293, deepest hole -0.321, 1-sigma level 0.044 Q1 1 0.6359 0.5733 0.5984 11.00000 0.05 0.29 Q2 1 0.6836 0.5180 0.8165 11.00000 0.05 0.25 Q3 1 0.6979 0.4372 0.7818 11.00000 0.05 0.23 Q4 1 0.6583 0.7997 0.5208 11.00000 0.05 0.22 Q5 1 0.6556 0.5067 0.7642 11.00000 0.05 0.22 Q6 1 0.6327 0.4157 0.6010 11.00000 0.05 0.21 Q7 1 0.6248 0.5144 0.6567 11.00000 0.05 0.20 Q8 1 0.5957 0.3740 0.8204 11.00000 0.05 0.19 ; _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+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 0.64268(2) 0.49773(3) 0.61765(2) 0.02783(12) Uani 1 1 d . . . . . O1 O 0.59036(7) 0.41733(9) 0.58329(5) 0.0338(3) Uani 1 1 d . . . . . O2 O 0.73662(7) 0.48354(10) 0.62873(5) 0.0371(3) Uani 1 1 d . . . . . O3 O 0.67047(7) 0.28498(9) 0.78188(5) 0.0343(3) Uani 1 1 d . . . . . N1 N 0.60127(9) 0.50486(12) 0.68328(5) 0.0293(3) Uani 1 1 d . . . . . H1 H 0.5486(13) 0.4894(15) 0.6803(8) 0.039(5) Uiso 1 1 d . . . . . N2 N 0.58151(8) 0.42614(11) 0.80413(5) 0.0258(3) Uani 1 1 d . . . . . C1 C 0.62739(10) 0.62405(13) 0.57838(6) 0.0271(3) Uani 1 1 d . . . . . C2 C 0.55553(10) 0.63746(14) 0.53586(7) 0.0300(3) Uani 1 1 d . . . . . H2 H 0.512709 0.580617 0.529489 0.036 Uiso 1 1 calc R U . . . C3 C 0.54652(11) 0.73419(14) 0.50271(7) 0.0327(4) Uani 1 1 d . . . . . H3 H 0.497417 0.742708 0.473278 0.039 Uiso 1 1 calc R U . . . C4 C 0.60738(11) 0.81894(14) 0.51141(7) 0.0333(4) Uani 1 1 d . . . . . C5 C 0.67843(12) 0.80451(15) 0.55526(8) 0.0405(4) Uani 1 1 d . . . . . H5 H 0.720273 0.862203 0.562566 0.049 Uiso 1 1 calc R U . . . C6 C 0.68910(11) 0.70804(15) 0.58822(7) 0.0368(4) Uani 1 1 d . . . . . H6 H 0.738364 0.699126 0.617482 0.044 Uiso 1 1 calc R U . . . C7 C 0.59862(13) 0.92299(15) 0.47373(8) 0.0440(4) Uani 1 1 d . . . . . H7A H 0.648187 0.928080 0.447275 0.068(4) Uiso 1 1 calc R U . . . H7B H 0.599560 0.986707 0.501255 0.068(4) Uiso 1 1 calc R U . . . H7C H 0.542414 0.921717 0.448223 0.068(4) Uiso 1 1 calc R U . . . C8 C 0.64518(10) 0.55997(13) 0.73616(6) 0.0277(3) Uani 1 1 d . . . . . H8A H 0.606633 0.619831 0.749599 0.033 Uiso 1 1 calc R U . . . H8B H 0.701263 0.593274 0.724315 0.033 Uiso 1 1 calc R U . . . C9 C 0.66567(10) 0.47947(13) 0.79001(6) 0.0260(3) Uani 1 1 d . . . . . C10 C 0.72415(10) 0.38152(14) 0.77228(7) 0.0304(4) Uani 1 1 d . . . . . H10A H 0.738410 0.386976 0.728797 0.037 Uiso 1 1 calc R U . . . H10B H 0.780276 0.379179 0.798747 0.037 Uiso 1 1 calc R U . . . C11 C 0.70598(10) 0.54218(13) 0.84532(6) 0.0264(3) Uani 1 1 d . . . . . C12 C 0.78479(11) 0.59953(17) 0.84105(7) 0.0417(4) Uani 1 1 d . . . . . H12 H 0.812103 0.600159 0.803173 0.050 Uiso 1 1 calc R U . . . C13 C 0.82425(12) 0.65578(17) 0.89098(8) 0.0443(5) Uani 1 1 d . . . . . H13 H 0.878282 0.694396 0.887247 0.053 Uiso 1 1 calc R U . . . C14 C 0.78519(11) 0.65579(14) 0.94611(7) 0.0363(4) Uani 1 1 d . . . . . H14 H 0.812188 0.694038 0.980558 0.044 Uiso 1 1 calc R U . . . C15 C 0.70647(11) 0.59974(14) 0.95086(7) 0.0350(4) Uani 1 1 d . . . . . H15 H 0.679161 0.600002 0.988739 0.042 Uiso 1 1 calc R U . . . C16 C 0.66685(10) 0.54308(13) 0.90097(6) 0.0294(3) Uani 1 1 d . . . . . H16 H 0.612738 0.504736 0.904866 0.035 Uiso 1 1 calc R U . . . C17 C 0.59135(10) 0.32356(14) 0.79858(7) 0.0300(3) Uani 1 1 d . . . . . C18 C 0.52269(11) 0.23804(14) 0.80765(8) 0.0391(4) Uani 1 1 d . . . . . H18A H 0.468016 0.274336 0.819884 0.047 Uiso 1 1 calc R U . . . H18B H 0.544456 0.188819 0.841624 0.047 Uiso 1 1 calc R U . . . C19 C 0.500000 0.1691(2) 0.750000 0.0439(6) Uani 1 2 d S T P . . H19A H 0.551172 0.121101 0.742807 0.053 Uiso 0.5 1 calc R U P . . H19B H 0.448829 0.121100 0.757193 0.053 Uiso 0.5 1 calc R U P . . 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 0.0270(2) 0.0405(2) 0.01674(18) -0.00089(15) 0.00659(13) -0.00413(16) O1 0.0411(7) 0.0371(6) 0.0234(5) -0.0028(5) 0.0042(5) -0.0062(5) O2 0.0284(6) 0.0578(8) 0.0264(6) 0.0045(5) 0.0096(4) 0.0012(5) O3 0.0281(6) 0.0376(6) 0.0387(6) 0.0048(5) 0.0117(5) 0.0084(5) N1 0.0237(7) 0.0485(8) 0.0164(6) -0.0006(5) 0.0052(5) -0.0076(6) N2 0.0242(6) 0.0344(7) 0.0194(6) 0.0037(5) 0.0066(5) 0.0024(5) C1 0.0279(8) 0.0381(9) 0.0163(7) -0.0035(6) 0.0076(6) -0.0066(7) C2 0.0276(8) 0.0371(9) 0.0256(7) -0.0040(7) 0.0038(6) -0.0108(7) C3 0.0302(9) 0.0408(9) 0.0271(8) -0.0019(7) 0.0020(6) -0.0060(7) C4 0.0358(9) 0.0383(9) 0.0270(8) -0.0025(7) 0.0101(7) -0.0066(7) C5 0.0418(10) 0.0430(10) 0.0365(9) -0.0022(8) 0.0018(8) -0.0215(8) C6 0.0334(9) 0.0513(11) 0.0251(8) -0.0023(7) -0.0012(6) -0.0144(8) C7 0.0493(11) 0.0397(10) 0.0440(10) 0.0032(8) 0.0100(8) -0.0081(8) C8 0.0275(8) 0.0385(9) 0.0175(7) 0.0015(6) 0.0040(6) -0.0025(7) C9 0.0228(7) 0.0379(9) 0.0181(7) 0.0016(6) 0.0063(5) 0.0009(6) C10 0.0244(8) 0.0427(9) 0.0252(7) 0.0002(7) 0.0090(6) 0.0026(7) C11 0.0245(7) 0.0367(8) 0.0183(7) 0.0020(6) 0.0048(6) 0.0042(6) C12 0.0339(9) 0.0701(13) 0.0219(8) -0.0020(8) 0.0092(7) -0.0111(9) C13 0.0398(10) 0.0629(13) 0.0307(9) -0.0039(8) 0.0052(7) -0.0147(9) C14 0.0419(10) 0.0415(10) 0.0254(8) -0.0061(7) 0.0024(7) 0.0027(8) C15 0.0448(10) 0.0402(10) 0.0214(7) -0.0012(7) 0.0123(7) 0.0047(8) C16 0.0329(8) 0.0340(8) 0.0225(7) 0.0023(6) 0.0093(6) 0.0043(7) C17 0.0265(8) 0.0394(9) 0.0249(7) 0.0081(7) 0.0082(6) 0.0066(7) C18 0.0347(9) 0.0368(9) 0.0480(10) 0.0152(8) 0.0173(8) 0.0055(7) C19 0.0335(13) 0.0292(13) 0.0716(18) 0.000 0.0215(12) 0.000 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 -1.00 0.00 0.1410 1.00 1.00 0.00 0.1390 1.00 -1.00 1.00 0.1620 0.00 0.00 -1.00 0.1380 0.00 0.00 1.00 0.1760 0.00 -1.00 0.00 0.1850 0.00 1.00 0.00 0.1580 -1.00 1.00 0.00 0.1150 1.00 -1.00 0.00 0.1650 1.00 0.00 -2.00 0.1640 1.00 1.00 1.00 0.1640 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 N1 105.50(7) . . ? O1 S C1 107.03(7) . . ? O2 S O1 120.45(7) . . ? O2 S N1 107.56(7) . . ? O2 S C1 106.22(7) . . ? N1 S C1 109.86(7) . . ? C17 O3 C10 105.69(12) . . ? S N1 H1 111.0(13) . . ? C8 N1 S 123.25(11) . . ? C8 N1 H1 123.7(13) . . ? C17 N2 C9 107.73(12) . . ? C2 C1 S 119.71(12) . . ? C2 C1 C6 120.04(15) . . ? C6 C1 S 120.20(12) . . ? C1 C2 H2 120.2 . . ? C3 C2 C1 119.53(14) . . ? C3 C2 H2 120.2 . . ? C2 C3 H3 119.2 . . ? C2 C3 C4 121.56(15) . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 117.98(15) . . ? C3 C4 C7 121.28(15) . . ? C5 C4 C7 120.73(15) . . ? C4 C5 H5 119.4 . . ? C6 C5 C4 121.26(15) . . ? C6 C5 H5 119.4 . . ? C1 C6 H6 120.2 . . ? C5 C6 C1 119.61(15) . . ? C5 C6 H6 120.2 . . ? C4 C7 H7A 109.5 . . ? C4 C7 H7B 109.5 . . ? C4 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? N1 C8 C9 111.46(13) . . ? H8A C8 H8B 108.0 . . ? C9 C8 H8A 109.3 . . ? C9 C8 H8B 109.3 . . ? N2 C9 C8 108.04(11) . . ? N2 C9 C10 103.21(12) . . ? N2 C9 C11 110.84(11) . . ? C8 C9 C10 112.61(12) . . ? C11 C9 C8 109.41(12) . . ? C11 C9 C10 112.51(12) . . ? O3 C10 C9 104.61(11) . . ? O3 C10 H10A 110.8 . . ? O3 C10 H10B 110.8 . . ? C9 C10 H10A 110.8 . . ? C9 C10 H10B 110.8 . . ? H10A C10 H10B 108.9 . . ? C12 C11 C9 119.68(13) . . ? C12 C11 C16 118.46(14) . . ? C16 C11 C9 121.85(14) . . ? C11 C12 H12 119.4 . . ? C13 C12 C11 121.15(15) . . ? C13 C12 H12 119.4 . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 120.00(16) . . ? C14 C13 H13 120.0 . . ? C13 C14 H14 120.3 . . ? C13 C14 C15 119.44(15) . . ? C15 C14 H14 120.3 . . ? C14 C15 H15 119.6 . . ? C14 C15 C16 120.71(14) . . ? C16 C15 H15 119.6 . . ? C11 C16 H16 119.9 . . ? C15 C16 C11 120.23(15) . . ? C15 C16 H16 119.9 . . ? O3 C17 C18 115.32(14) . . ? N2 C17 O3 118.62(14) . . ? N2 C17 C18 126.05(14) . . ? C17 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C17 C18 C19 112.92(13) . . ? H18A C18 H18B 107.8 . . ? C19 C18 H18A 109.0 . . ? C19 C18 H18B 109.0 . . ? C18 C19 C18 113.5(2) 2_656 . ? C18 C19 H19A 108.9 . . ? C18 C19 H19A 108.9 2_656 . ? C18 C19 H19B 108.9 2_656 . ? C18 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? 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 1.4338(11) . ? S O2 1.4315(12) . ? S N1 1.6059(12) . ? S C1 1.7665(16) . ? O3 C10 1.451(2) . ? O3 C17 1.3578(18) . ? N1 H1 0.81(2) . ? N1 C8 1.4516(19) . ? N2 C9 1.4790(19) . ? N2 C17 1.264(2) . ? C1 C2 1.384(2) . ? C1 C6 1.389(2) . ? C2 H2 0.9500 . ? C2 C3 1.383(2) . ? C3 H3 0.9500 . ? C3 C4 1.385(2) . ? C4 C5 1.395(2) . ? C4 C7 1.510(2) . ? C5 H5 0.9500 . ? C5 C6 1.380(2) . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.543(2) . ? C9 C10 1.549(2) . ? C9 C11 1.517(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.388(2) . ? C11 C16 1.388(2) . ? C12 H12 0.9500 . ? C12 C13 1.384(2) . ? C13 H13 0.9500 . ? C13 C14 1.378(2) . ? C14 H14 0.9500 . ? C14 C15 1.381(2) . ? C15 H15 0.9500 . ? C15 C16 1.386(2) . ? C16 H16 0.9500 . ? C17 C18 1.492(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C18 C19 1.529(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? 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 N1 H1 N2 0.81(2) 2.16(2) 2.9526(18) 164.4(18) 2_656 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 N1 C8 C9 -118.73(13) . . . . ? S C1 C2 C3 -176.39(12) . . . . ? S C1 C6 C5 177.16(13) . . . . ? O1 S N1 C8 167.22(12) . . . . ? O1 S C1 C2 18.07(14) . . . . ? O1 S C1 C6 -159.31(12) . . . . ? O2 S N1 C8 37.47(15) . . . . ? O2 S C1 C2 147.95(12) . . . . ? O2 S C1 C6 -29.43(14) . . . . ? O3 C17 C18 C19 -59.03(18) . . . . ? N1 S C1 C2 -95.99(13) . . . . ? N1 S C1 C6 86.63(14) . . . . ? N1 C8 C9 N2 -55.62(15) . . . . ? N1 C8 C9 C10 57.70(16) . . . . ? N1 C8 C9 C11 -176.38(12) . . . . ? N2 C9 C10 O3 -3.55(14) . . . . ? N2 C9 C11 C12 -179.03(14) . . . . ? N2 C9 C11 C16 1.8(2) . . . . ? N2 C17 C18 C19 119.84(17) . . . . ? C1 S N1 C8 -77.74(14) . . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C2 C1 C6 C5 -0.2(2) . . . . ? C2 C3 C4 C5 -0.5(2) . . . . ? C2 C3 C4 C7 178.17(15) . . . . ? C3 C4 C5 C6 1.3(3) . . . . ? C4 C5 C6 C1 -1.0(3) . . . . ? C6 C1 C2 C3 1.0(2) . . . . ? C7 C4 C5 C6 -177.37(16) . . . . ? C8 C9 C10 O3 -119.80(13) . . . . ? C8 C9 C11 C12 -59.98(18) . . . . ? C8 C9 C11 C16 120.83(15) . . . . ? C9 N2 C17 O3 -0.24(18) . . . . ? C9 N2 C17 C18 -179.08(14) . . . . ? C9 C11 C12 C13 -178.71(17) . . . . ? C9 C11 C16 C15 178.85(14) . . . . ? C10 O3 C17 N2 -2.22(18) . . . . ? C10 O3 C17 C18 176.74(13) . . . . ? C10 C9 C11 C12 65.98(19) . . . . ? C10 C9 C11 C16 -113.20(16) . . . . ? C11 C9 C10 O3 115.98(13) . . . . ? C11 C12 C13 C14 -0.2(3) . . . . ? C12 C11 C16 C15 -0.3(2) . . . . ? C12 C13 C14 C15 -0.3(3) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C14 C15 C16 C11 -0.1(2) . . . . ? C16 C11 C12 C13 0.5(3) . . . . ? C17 O3 C10 C9 3.46(15) . . . . ? C17 N2 C9 C8 121.86(13) . . . . ? C17 N2 C9 C10 2.41(15) . . . . ? C17 N2 C9 C11 -118.27(14) . . . . ? C17 C18 C19 C18 -51.08(10) . . . 2_656 ? loop_ _smtbx_masks_void_nr _smtbx_masks_void_average_x _smtbx_masks_void_average_y _smtbx_masks_void_average_z _smtbx_masks_void_volume _smtbx_masks_void_count_electrons _smtbx_masks_void_content 1 0.000 0.354 0.750 197.9 49.4 '1 C4H8O2' 2 0.000 0.646 0.250 197.9 49.4 '1 C4H8O2' 3 0.500 0.146 0.250 197.9 49.4 '1 C4H8O2' 4 0.500 0.854 0.750 197.9 49.4 '1 C4H8O2'