#------------------------------------------------------------------------------ #$Date: 2020-05-13 02:20:41 +0300 (Wed, 13 May 2020) $ #$Revision: 252000 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038355.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_4038355 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 'C25 H32 N2 O3 S' _chemical_formula_sum 'C25 H32 N2 O3 S' _chemical_formula_weight 440.58 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2019-10-19 _audit_creation_method ; Olex2 1.3-alpha (compiled 2019.10.11 svn.r3662 for OlexSys, GUI svn.r5962) ; _cell_angle_alpha 90 _cell_angle_beta 102.914(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.5408(7) _cell_length_b 11.4873(7) _cell_length_c 19.3042(13) _cell_measurement_reflns_used 9870 _cell_measurement_temperature 120 _cell_measurement_theta_max 29.68 _cell_measurement_theta_min 2.46 _cell_volume 2278.3(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 0.999 _diffrn_measured_fraction_theta_max 0.998 _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 0.0431 _diffrn_reflns_av_unetI/netI 0.0318 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 49671 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 30.000 _diffrn_reflns_theta_max 30.127 _diffrn_reflns_theta_min 2.165 _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 0.171 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker, 2016) was used for absorption correction. wR2(int) was 0.0638 before and 0.0439 after correction. The Ratio of minimum to maximum transmission is 0.9575. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.284 _exptl_crystal_description block _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.229 _exptl_crystal_size_mid 0.151 _exptl_crystal_size_min 0.122 _refine_diff_density_max 0.411 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.052 _refine_ls_extinction_coef 0.0028(9) _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 1.038 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 285 _refine_ls_number_reflns 6697 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0591 _refine_ls_R_factor_gt 0.0396 _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^)+(0.0535P)^2^+0.7160P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0970 _refine_ls_wR_factor_ref 0.1044 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5211 _reflns_number_total 6697 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 19srv307.cif _cod_data_source_block 19srv307 _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 4038355 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Others Uiso(H18A)=Uiso(H18B)=Uiso(H18C)=FVAR(1) Uiso(H25A)=Uiso(H25B)=Uiso(H25C)=FVAR(2) 3.a Secondary CH2 refined with riding coordinates: C1(H1A,H1B), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B) 3.b Aromatic/amide H refined with riding coordinates: C13(H13), C14(H14), C16(H16), C17(H17), C20(H20), C21(H21), C23(H23), C24(H24) 3.c Idealised Me refined as rotating group: C18(H18A,H18B,H18C), C25(H25A,H25B,H25C) ; _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 0.962 _shelx_estimated_absorpt_t_max 0.979 _shelx_res_checksum 91906 _shelx_res_file ; TITL 19srv307_a.res in P2(1)/n 19srv307.res created by SHELXL-2018/3 at 15:23:46 on 18-Oct-2019 REM Old TITL 19srv307 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.111, Rweak 0.005, Alpha 0.030 REM 0.391 for 248 systematic absences, Orientation as input REM Formula found by SHELXT: C25 N2 O3 S CELL 0.71073 10.5408 11.4873 19.3042 90 102.914 90 ZERR 4 0.0007 0.0007 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 100 128 8 12 4 L.S. 7 PLAN 5 SIZE 0.122 0.151 0.229 TEMP -153.15 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta 60 OMIT -1 0 1 OMIT 0 1 1 REM REM REM WGHT 0.053500 0.716000 EXTI 0.002843 FVAR 0.71090 0.06188 0.03546 S 5 0.089149 0.600305 0.390214 11.00000 0.01582 0.01353 = 0.01627 -0.00042 0.00295 -0.00232 O1 4 0.051434 0.635457 0.317374 11.00000 0.02340 0.02167 = 0.01742 0.00073 0.00202 -0.00111 O2 4 0.007499 0.522136 0.418179 11.00000 0.01900 0.01781 = 0.02393 0.00113 0.00529 -0.00499 O3 4 0.376945 0.369279 0.265645 11.00000 0.01994 0.01484 = 0.01933 -0.00230 -0.00100 0.00341 N1 3 0.234105 0.538826 0.400296 11.00000 0.01677 0.01330 = 0.01793 0.00004 0.00470 -0.00109 N2 3 0.490545 0.457025 0.365152 11.00000 0.01512 0.01371 = 0.01818 0.00245 0.00230 -0.00105 C1 1 0.328592 0.612466 0.373899 11.00000 0.01913 0.01383 = 0.02320 -0.00329 0.00759 -0.00362 AFIX 23 H1A 2 0.391024 0.645406 0.415308 11.00000 -1.20000 H1B 2 0.280965 0.678344 0.346857 11.00000 -1.20000 AFIX 0 C2 1 0.405910 0.549550 0.326187 11.00000 0.01411 0.01279 = 0.01764 0.00011 0.00284 -0.00116 C3 1 0.317120 0.483089 0.264265 11.00000 0.01579 0.01401 = 0.01884 -0.00079 0.00196 0.00169 AFIX 23 H3A 2 0.227441 0.476774 0.271702 11.00000 -1.20000 H3B 2 0.314292 0.522683 0.218393 11.00000 -1.20000 AFIX 0 C4 1 0.471243 0.366185 0.327095 11.00000 0.01312 0.01693 = 0.01616 0.00249 0.00288 -0.00089 C5 1 0.545010 0.253843 0.339214 11.00000 0.01663 0.01623 = 0.02382 0.00160 0.00388 0.00213 AFIX 23 H5A 2 0.618029 0.263165 0.381125 11.00000 -1.20000 H5B 2 0.583040 0.238578 0.297617 11.00000 -1.20000 AFIX 0 C6 1 0.465033 0.147007 0.351196 11.00000 0.02246 0.01464 = 0.02722 0.00075 0.00310 0.00149 AFIX 23 H6A 2 0.374223 0.157456 0.324129 11.00000 -1.20000 H6B 2 0.500684 0.077388 0.332015 11.00000 -1.20000 AFIX 0 C7 1 0.464227 0.125159 0.429351 11.00000 0.02310 0.02022 = 0.03063 0.00905 0.00529 0.00405 AFIX 23 H7A 2 0.407834 0.057163 0.432066 11.00000 -1.20000 H7B 2 0.553620 0.104567 0.454969 11.00000 -1.20000 AFIX 0 C8 1 0.417391 0.227011 0.467551 11.00000 0.02163 0.02527 = 0.02047 0.00682 0.00177 0.00231 AFIX 23 H8A 2 0.477453 0.293351 0.467826 11.00000 -1.20000 H8B 2 0.422542 0.204398 0.517591 11.00000 -1.20000 AFIX 0 C9 1 0.278688 0.267848 0.435198 11.00000 0.01942 0.01661 = 0.02529 0.00514 0.00294 -0.00178 AFIX 23 H9A 2 0.274873 0.297600 0.386644 11.00000 -1.20000 H9B 2 0.218949 0.200451 0.431184 11.00000 -1.20000 AFIX 0 C10 1 0.232166 0.362727 0.478717 11.00000 0.02913 0.02465 = 0.02448 0.00912 0.01207 0.00412 AFIX 23 H10A 2 0.136014 0.366780 0.464659 11.00000 -1.20000 H10B 2 0.256027 0.340353 0.529499 11.00000 -1.20000 AFIX 0 C11 1 0.287044 0.483195 0.470706 11.00000 0.02407 0.02008 = 0.01758 -0.00136 0.00179 0.00333 AFIX 23 H11A 2 0.268188 0.534285 0.508469 11.00000 -1.20000 H11B 2 0.382811 0.477185 0.477990 11.00000 -1.20000 AFIX 0 C12 1 0.110159 0.726901 0.443231 11.00000 0.01417 0.01462 = 0.01981 -0.00062 0.00495 -0.00040 C13 1 0.135108 0.832477 0.413556 11.00000 0.02342 0.01681 = 0.02293 0.00027 0.00932 -0.00066 AFIX 43 H13 2 0.136807 0.837271 0.364642 11.00000 -1.20000 AFIX 0 C14 1 0.157403 0.930358 0.456278 11.00000 0.02429 0.01485 = 0.03372 -0.00066 0.01049 -0.00182 AFIX 43 H14 2 0.174381 1.002509 0.436061 11.00000 -1.20000 AFIX 0 C15 1 0.155619 0.925937 0.528173 11.00000 0.01511 0.02017 = 0.03058 -0.00722 0.00338 0.00123 C16 1 0.127718 0.819769 0.556293 11.00000 0.01869 0.02561 = 0.01913 -0.00372 0.00424 0.00276 AFIX 43 H16 2 0.123980 0.815464 0.604942 11.00000 -1.20000 AFIX 0 C17 1 0.105206 0.719868 0.514567 11.00000 0.01614 0.01891 = 0.02124 0.00140 0.00581 0.00081 AFIX 43 H17 2 0.086725 0.647907 0.534480 11.00000 -1.20000 AFIX 0 C18 1 0.185242 1.033058 0.573974 11.00000 0.03144 0.02539 = 0.03962 -0.01541 0.00408 -0.00142 AFIX 137 H18A 2 0.153362 1.022204 0.617492 11.00000 21.00000 H18B 2 0.142132 1.100608 0.547857 11.00000 21.00000 H18C 2 0.279502 1.046039 0.586363 11.00000 21.00000 AFIX 0 C19 1 0.489580 0.641893 0.300576 11.00000 0.01624 0.01324 = 0.01877 -0.00081 0.00498 -0.00014 C20 1 0.624366 0.642891 0.322259 11.00000 0.01677 0.01525 = 0.01987 0.00106 0.00391 0.00175 AFIX 43 H20 2 0.667225 0.583534 0.353061 11.00000 -1.20000 AFIX 0 C21 1 0.697520 0.729972 0.299359 11.00000 0.01374 0.02006 = 0.02534 -0.00046 0.00503 -0.00120 AFIX 43 H21 2 0.789607 0.729205 0.315019 11.00000 -1.20000 AFIX 0 C22 1 0.638370 0.817700 0.254141 11.00000 0.01898 0.01606 = 0.02501 -0.00066 0.00890 -0.00077 C23 1 0.503152 0.815647 0.231635 11.00000 0.02030 0.01978 = 0.03260 0.01032 0.00590 0.00291 AFIX 43 H23 2 0.460558 0.874030 0.199963 11.00000 -1.20000 AFIX 0 C24 1 0.429841 0.729808 0.254719 11.00000 0.01357 0.02196 = 0.03229 0.00806 0.00288 -0.00016 AFIX 43 H24 2 0.337743 0.730795 0.239140 11.00000 -1.20000 AFIX 0 C25 1 0.715414 0.913376 0.229387 11.00000 0.02300 0.02168 = 0.03400 0.00483 0.01096 -0.00362 AFIX 137 H25A 2 0.682098 0.989128 0.240512 11.00000 31.00000 H25B 2 0.706993 0.906942 0.177936 11.00000 31.00000 H25C 2 0.807272 0.906298 0.253608 11.00000 31.00000 AFIX 0 HKLF 4 REM 19srv307_a.res in P2(1)/n REM wR2 = 0.1044, GooF = S = 1.038, Restrained GooF = 1.038 for all data REM R1 = 0.0396 for 5211 Fo > 4sig(Fo) and 0.0591 for all 6697 data REM 285 parameters refined using 0 restraints END WGHT 0.0536 0.7132 REM Highest difference peak 0.411, deepest hole -0.404, 1-sigma level 0.052 Q1 1 0.3586 0.5194 0.2968 11.00000 0.05 0.41 Q2 1 0.1063 0.6636 0.4200 11.00000 0.05 0.37 Q3 1 0.3790 0.5773 0.3574 11.00000 0.05 0.34 Q4 1 0.1680 0.5710 0.3967 11.00000 0.05 0.34 Q5 1 0.0550 0.5608 0.4192 11.00000 0.05 0.33 ; _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 0.08915(3) 0.60031(3) 0.39021(2) 0.01531(8) Uani 1 1 d . . . . . O1 O 0.05143(9) 0.63546(8) 0.31737(5) 0.0212(2) Uani 1 1 d . . . . . O2 O 0.00750(9) 0.52214(8) 0.41818(5) 0.02017(19) Uani 1 1 d . . . . . O3 O 0.37695(9) 0.36928(7) 0.26564(5) 0.01888(19) Uani 1 1 d . . . . . N1 N 0.23411(10) 0.53883(9) 0.40030(5) 0.0159(2) Uani 1 1 d . . . . . N2 N 0.49055(10) 0.45703(9) 0.36515(5) 0.0159(2) Uani 1 1 d . . . . . C1 C 0.32859(12) 0.61247(10) 0.37390(7) 0.0183(2) Uani 1 1 d . . . . . H1A H 0.391024 0.645406 0.415308 0.022 Uiso 1 1 calc R U . . . H1B H 0.280965 0.678344 0.346857 0.022 Uiso 1 1 calc R U . . . C2 C 0.40591(11) 0.54955(10) 0.32619(6) 0.0150(2) Uani 1 1 d . . . . . C3 C 0.31712(12) 0.48309(10) 0.26426(7) 0.0165(2) Uani 1 1 d . . . . . H3A H 0.227441 0.476774 0.271702 0.020 Uiso 1 1 calc R U . . . H3B H 0.314292 0.522683 0.218393 0.020 Uiso 1 1 calc R U . . . C4 C 0.47124(11) 0.36619(11) 0.32709(6) 0.0155(2) Uani 1 1 d . . . . . C5 C 0.54501(12) 0.25384(11) 0.33921(7) 0.0190(2) Uani 1 1 d . . . . . H5A H 0.618029 0.263165 0.381125 0.023 Uiso 1 1 calc R U . . . H5B H 0.583040 0.238578 0.297617 0.023 Uiso 1 1 calc R U . . . C6 C 0.46503(13) 0.14701(11) 0.35120(7) 0.0218(3) Uani 1 1 d . . . . . H6A H 0.374223 0.157456 0.324129 0.026 Uiso 1 1 calc R U . . . H6B H 0.500684 0.077388 0.332015 0.026 Uiso 1 1 calc R U . . . C7 C 0.46423(14) 0.12516(12) 0.42935(8) 0.0248(3) Uani 1 1 d . . . . . H7A H 0.407834 0.057163 0.432066 0.030 Uiso 1 1 calc R U . . . H7B H 0.553620 0.104567 0.454969 0.030 Uiso 1 1 calc R U . . . C8 C 0.41739(13) 0.22701(12) 0.46755(7) 0.0229(3) Uani 1 1 d . . . . . H8A H 0.477453 0.293351 0.467826 0.027 Uiso 1 1 calc R U . . . H8B H 0.422542 0.204398 0.517591 0.027 Uiso 1 1 calc R U . . . C9 C 0.27869(12) 0.26785(11) 0.43520(7) 0.0208(3) Uani 1 1 d . . . . . H9A H 0.274873 0.297600 0.386644 0.025 Uiso 1 1 calc R U . . . H9B H 0.218949 0.200451 0.431184 0.025 Uiso 1 1 calc R U . . . C10 C 0.23217(14) 0.36273(12) 0.47872(8) 0.0251(3) Uani 1 1 d . . . . . H10A H 0.136014 0.366780 0.464659 0.030 Uiso 1 1 calc R U . . . H10B H 0.256027 0.340353 0.529499 0.030 Uiso 1 1 calc R U . . . C11 C 0.28704(13) 0.48320(11) 0.47071(7) 0.0210(3) Uani 1 1 d . . . . . H11A H 0.268188 0.534285 0.508469 0.025 Uiso 1 1 calc R U . . . H11B H 0.382811 0.477185 0.477990 0.025 Uiso 1 1 calc R U . . . C12 C 0.11016(11) 0.72690(10) 0.44323(7) 0.0160(2) Uani 1 1 d . . . . . C13 C 0.13511(13) 0.83248(11) 0.41356(7) 0.0204(3) Uani 1 1 d . . . . . H13 H 0.136807 0.837271 0.364642 0.024 Uiso 1 1 calc R U . . . C14 C 0.15740(13) 0.93036(11) 0.45628(8) 0.0237(3) Uani 1 1 d . . . . . H14 H 0.174381 1.002509 0.436061 0.028 Uiso 1 1 calc R U . . . C15 C 0.15562(12) 0.92594(11) 0.52817(8) 0.0222(3) Uani 1 1 d . . . . . C16 C 0.12772(12) 0.81977(12) 0.55629(7) 0.0211(3) Uani 1 1 d . . . . . H16 H 0.123980 0.815464 0.604942 0.025 Uiso 1 1 calc R U . . . C17 C 0.10521(12) 0.71987(11) 0.51457(7) 0.0185(2) Uani 1 1 d . . . . . H17 H 0.086725 0.647907 0.534480 0.022 Uiso 1 1 calc R U . . . C18 C 0.18524(15) 1.03306(13) 0.57397(9) 0.0328(3) Uani 1 1 d . . . . . H18A H 0.153362 1.022204 0.617492 0.062(4) Uiso 1 1 calc R U . . . H18B H 0.142132 1.100608 0.547857 0.062(4) Uiso 1 1 calc R U . . . H18C H 0.279502 1.046039 0.586363 0.062(4) Uiso 1 1 calc R U . . . C19 C 0.48958(12) 0.64189(10) 0.30058(7) 0.0159(2) Uani 1 1 d . . . . . C20 C 0.62437(12) 0.64289(11) 0.32226(7) 0.0173(2) Uani 1 1 d . . . . . H20 H 0.667225 0.583534 0.353061 0.021 Uiso 1 1 calc R U . . . C21 C 0.69752(12) 0.72997(11) 0.29936(7) 0.0196(3) Uani 1 1 d . . . . . H21 H 0.789607 0.729205 0.315019 0.024 Uiso 1 1 calc R U . . . C22 C 0.63837(12) 0.81770(11) 0.25414(7) 0.0194(3) Uani 1 1 d . . . . . C23 C 0.50315(13) 0.81565(12) 0.23164(8) 0.0242(3) Uani 1 1 d . . . . . H23 H 0.460558 0.874030 0.199963 0.029 Uiso 1 1 calc R U . . . C24 C 0.42984(12) 0.72981(12) 0.25472(8) 0.0230(3) Uani 1 1 d . . . . . H24 H 0.337743 0.730795 0.239140 0.028 Uiso 1 1 calc R U . . . C25 C 0.71541(13) 0.91338(12) 0.22939(8) 0.0255(3) Uani 1 1 d . . . . . H25A H 0.682098 0.989128 0.240512 0.035(3) Uiso 1 1 calc R U . . . H25B H 0.706993 0.906942 0.177936 0.035(3) Uiso 1 1 calc R U . . . H25C H 0.807272 0.906298 0.253608 0.035(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 0.01582(14) 0.01353(14) 0.01627(15) -0.00042(11) 0.00295(11) -0.00232(10) O1 0.0234(5) 0.0217(5) 0.0174(4) 0.0007(4) 0.0020(4) -0.0011(4) O2 0.0190(4) 0.0178(4) 0.0239(5) 0.0011(4) 0.0053(4) -0.0050(3) O3 0.0199(4) 0.0148(4) 0.0193(4) -0.0023(3) -0.0010(3) 0.0034(3) N1 0.0168(5) 0.0133(5) 0.0179(5) 0.0000(4) 0.0047(4) -0.0011(4) N2 0.0151(5) 0.0137(5) 0.0182(5) 0.0025(4) 0.0023(4) -0.0011(4) C1 0.0191(6) 0.0138(5) 0.0232(6) -0.0033(5) 0.0076(5) -0.0036(4) C2 0.0141(5) 0.0128(5) 0.0176(6) 0.0001(4) 0.0028(4) -0.0012(4) C3 0.0158(5) 0.0140(5) 0.0188(6) -0.0008(4) 0.0020(5) 0.0017(4) C4 0.0131(5) 0.0169(6) 0.0162(6) 0.0025(4) 0.0029(4) -0.0009(4) C5 0.0166(6) 0.0162(6) 0.0238(6) 0.0016(5) 0.0039(5) 0.0021(4) C6 0.0225(6) 0.0146(6) 0.0272(7) 0.0008(5) 0.0031(5) 0.0015(5) C7 0.0231(6) 0.0202(6) 0.0306(7) 0.0091(5) 0.0053(6) 0.0040(5) C8 0.0216(6) 0.0253(7) 0.0205(6) 0.0068(5) 0.0018(5) 0.0023(5) C9 0.0194(6) 0.0166(6) 0.0253(7) 0.0051(5) 0.0029(5) -0.0018(5) C10 0.0291(7) 0.0246(7) 0.0245(7) 0.0091(5) 0.0121(6) 0.0041(5) C11 0.0241(6) 0.0201(6) 0.0176(6) -0.0014(5) 0.0018(5) 0.0033(5) C12 0.0142(5) 0.0146(5) 0.0198(6) -0.0006(5) 0.0049(4) -0.0004(4) C13 0.0234(6) 0.0168(6) 0.0229(6) 0.0003(5) 0.0093(5) -0.0007(5) C14 0.0243(6) 0.0148(6) 0.0337(7) -0.0007(5) 0.0105(6) -0.0018(5) C15 0.0151(6) 0.0202(6) 0.0306(7) -0.0072(5) 0.0034(5) 0.0012(5) C16 0.0187(6) 0.0256(7) 0.0191(6) -0.0037(5) 0.0042(5) 0.0028(5) C17 0.0161(6) 0.0189(6) 0.0212(6) 0.0014(5) 0.0058(5) 0.0008(5) C18 0.0314(8) 0.0254(7) 0.0396(9) -0.0154(7) 0.0041(7) -0.0014(6) C19 0.0162(6) 0.0132(5) 0.0188(6) -0.0008(4) 0.0050(5) -0.0001(4) C20 0.0168(6) 0.0153(5) 0.0199(6) 0.0011(5) 0.0039(5) 0.0017(4) C21 0.0137(5) 0.0201(6) 0.0253(6) -0.0005(5) 0.0050(5) -0.0012(5) C22 0.0190(6) 0.0161(6) 0.0250(7) -0.0007(5) 0.0089(5) -0.0008(5) C23 0.0203(6) 0.0198(6) 0.0326(7) 0.0103(6) 0.0059(5) 0.0029(5) C24 0.0136(6) 0.0220(6) 0.0323(7) 0.0081(5) 0.0029(5) -0.0002(5) C25 0.0230(7) 0.0217(7) 0.0340(8) 0.0048(6) 0.0110(6) -0.0036(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 0.00 1.00 0.0750 1.00 0.00 -1.00 0.0790 -1.00 0.00 1.00 0.0840 0.00 -1.00 0.00 0.0600 0.00 -1.00 -1.00 0.0610 0.00 1.00 1.00 0.0400 0.00 -1.00 1.00 0.0580 0.00 1.00 -2.00 0.0550 1.00 1.00 -2.00 0.0620 -1.00 -1.00 2.00 0.0810 1.00 1.00 1.00 0.0850 -1.00 -1.00 -1.00 0.1180 1.00 -2.00 1.00 0.0810 -1.00 2.00 -1.00 0.0780 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 106.40(6) . . ? O1 S C12 107.99(6) . . ? O2 S O1 119.30(6) . . ? O2 S N1 107.78(5) . . ? O2 S C12 107.86(6) . . ? N1 S C12 106.90(5) . . ? C4 O3 C3 105.57(9) . . ? C1 N1 S 112.95(8) . . ? C1 N1 C11 114.49(10) . . ? C11 N1 S 115.93(8) . . ? C4 N2 C2 107.24(10) . . ? N1 C1 H1A 108.5 . . ? N1 C1 H1B 108.5 . . ? N1 C1 C2 115.10(9) . . ? H1A C1 H1B 107.5 . . ? C2 C1 H1A 108.5 . . ? C2 C1 H1B 108.5 . . ? N2 C2 C1 111.87(10) . . ? N2 C2 C3 103.32(9) . . ? N2 C2 C19 109.66(9) . . ? C1 C2 C3 112.62(10) . . ? C19 C2 C1 106.75(9) . . ? C19 C2 C3 112.69(10) . . ? O3 C3 C2 104.22(9) . . ? O3 C3 H3A 110.9 . . ? O3 C3 H3B 110.9 . . ? C2 C3 H3A 110.9 . . ? C2 C3 H3B 110.9 . . ? H3A C3 H3B 108.9 . . ? O3 C4 C5 114.16(10) . . ? N2 C4 O3 118.25(11) . . ? N2 C4 C5 127.51(11) . . ? C4 C5 H5A 108.4 . . ? C4 C5 H5B 108.4 . . ? C4 C5 C6 115.39(10) . . ? H5A C5 H5B 107.5 . . ? C6 C5 H5A 108.4 . . ? C6 C5 H5B 108.4 . . ? C5 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C7 C6 C5 113.80(11) . . ? C7 C6 H6A 108.8 . . ? C7 C6 H6B 108.8 . . ? C6 C7 H7A 108.5 . . ? C6 C7 H7B 108.5 . . ? H7A C7 H7B 107.5 . . ? C8 C7 C6 115.15(11) . . ? C8 C7 H7A 108.5 . . ? C8 C7 H7B 108.5 . . ? C7 C8 H8A 108.5 . . ? C7 C8 H8B 108.5 . . ? C7 C8 C9 114.94(11) . . ? H8A C8 H8B 107.5 . . ? C9 C8 H8A 108.5 . . ? C9 C8 H8B 108.5 . . ? C8 C9 H9A 109.0 . . ? C8 C9 H9B 109.0 . . ? H9A C9 H9B 107.8 . . ? C10 C9 C8 112.99(11) . . ? C10 C9 H9A 109.0 . . ? C10 C9 H9B 109.0 . . ? C9 C10 H10A 108.6 . . ? C9 C10 H10B 108.6 . . ? H10A C10 H10B 107.6 . . ? C11 C10 C9 114.74(11) . . ? C11 C10 H10A 108.6 . . ? C11 C10 H10B 108.6 . . ? N1 C11 C10 114.13(11) . . ? N1 C11 H11A 108.7 . . ? N1 C11 H11B 108.7 . . ? C10 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 C12 S 119.38(10) . . ? C13 C12 C17 120.68(11) . . ? C17 C12 S 119.91(9) . . ? C12 C13 H13 120.5 . . ? C14 C13 C12 119.06(12) . . ? C14 C13 H13 120.5 . . ? C13 C14 H14 119.1 . . ? C13 C14 C15 121.74(12) . . ? C15 C14 H14 119.1 . . ? C14 C15 C18 120.51(13) . . ? C16 C15 C14 118.11(12) . . ? C16 C15 C18 121.37(13) . . ? C15 C16 H16 119.3 . . ? C17 C16 C15 121.33(12) . . ? C17 C16 H16 119.3 . . ? C12 C17 H17 120.5 . . ? C16 C17 C12 119.04(12) . . ? C16 C17 H17 120.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18B 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C2 122.21(11) . . ? C20 C19 C24 118.10(11) . . ? C24 C19 C2 119.68(11) . . ? C19 C20 H20 119.6 . . ? C19 C20 C21 120.77(11) . . ? C21 C20 H20 119.6 . . ? C20 C21 H21 119.4 . . ? C22 C21 C20 121.22(11) . . ? C22 C21 H21 119.4 . . ? C21 C22 C23 117.93(12) . . ? C21 C22 C25 122.10(12) . . ? C23 C22 C25 119.97(12) . . ? C22 C23 H23 119.5 . . ? C24 C23 C22 121.08(12) . . ? C24 C23 H23 119.5 . . ? C19 C24 H24 119.6 . . ? C23 C24 C19 120.88(12) . . ? C23 C24 H24 119.6 . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25B 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 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 1.4312(9) . ? S O2 1.4304(9) . ? S N1 1.6548(11) . ? S C12 1.7635(12) . ? O3 C3 1.4492(14) . ? O3 C4 1.3673(14) . ? N1 C1 1.4812(15) . ? N1 C11 1.4927(16) . ? N2 C2 1.4803(15) . ? N2 C4 1.2662(16) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.5396(17) . ? C2 C3 1.5452(16) . ? C2 C19 1.5305(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.4978(17) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.5354(18) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.531(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.523(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.5296(18) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.5226(19) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C11 1.5210(19) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.3912(17) . ? C12 C17 1.3920(18) . ? C13 H13 0.9500 . ? C13 C14 1.3831(19) . ? C14 H14 0.9500 . ? C14 C15 1.393(2) . ? C15 C16 1.3928(19) . ? C15 C18 1.5067(19) . ? C16 H16 0.9500 . ? C16 C17 1.3916(18) . ? C17 H17 0.9500 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.3885(17) . ? C19 C24 1.3967(17) . ? C20 H20 0.9500 . ? C20 C21 1.3939(17) . ? C21 H21 0.9500 . ? C21 C22 1.3867(18) . ? C22 C23 1.3943(18) . ? C22 C25 1.5064(18) . ? C23 H23 0.9500 . ? C23 C24 1.3864(18) . ? C24 H24 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 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 -132.45(9) . . . . ? S N1 C11 C10 80.13(12) . . . . ? S C12 C13 C14 -177.06(10) . . . . ? S C12 C17 C16 177.19(9) . . . . ? O1 S N1 C1 51.60(9) . . . . ? O1 S N1 C11 -173.46(8) . . . . ? O1 S C12 C13 -22.54(12) . . . . ? O1 S C12 C17 159.20(10) . . . . ? O2 S N1 C1 -179.34(8) . . . . ? O2 S N1 C11 -44.40(10) . . . . ? O2 S C12 C13 -152.73(10) . . . . ? O2 S C12 C17 29.01(12) . . . . ? O3 C4 C5 C6 -65.55(15) . . . . ? N1 S C12 C13 91.60(11) . . . . ? N1 S C12 C17 -86.66(11) . . . . ? N1 C1 C2 N2 -64.05(13) . . . . ? N1 C1 C2 C3 51.81(14) . . . . ? N1 C1 C2 C19 175.99(10) . . . . ? N2 C2 C3 O3 -11.60(12) . . . . ? N2 C2 C19 C20 -9.27(16) . . . . ? N2 C2 C19 C24 171.76(11) . . . . ? N2 C4 C5 C6 117.66(14) . . . . ? C1 N1 C11 C10 -145.61(11) . . . . ? C1 C2 C3 O3 -132.49(10) . . . . ? C1 C2 C19 C20 112.11(13) . . . . ? C1 C2 C19 C24 -66.86(14) . . . . ? C2 N2 C4 O3 -4.61(14) . . . . ? C2 N2 C4 C5 172.08(12) . . . . ? C2 C19 C20 C21 -178.36(11) . . . . ? C2 C19 C24 C23 178.93(12) . . . . ? C3 O3 C4 N2 -3.42(14) . . . . ? C3 O3 C4 C5 179.47(10) . . . . ? C3 C2 C19 C20 -123.75(12) . . . . ? C3 C2 C19 C24 57.28(15) . . . . ? C4 O3 C3 C2 9.32(12) . . . . ? C4 N2 C2 C1 131.36(10) . . . . ? C4 N2 C2 C3 9.96(12) . . . . ? C4 N2 C2 C19 -110.40(11) . . . . ? C4 C5 C6 C7 -90.35(14) . . . . ? C5 C6 C7 C8 55.90(15) . . . . ? C6 C7 C8 C9 59.51(16) . . . . ? C7 C8 C9 C10 175.10(11) . . . . ? C8 C9 C10 C11 76.62(15) . . . . ? C9 C10 C11 N1 71.28(15) . . . . ? C11 N1 C1 C2 91.93(13) . . . . ? C12 S N1 C1 -63.61(9) . . . . ? C12 S N1 C11 71.33(10) . . . . ? C12 C13 C14 C15 0.0(2) . . . . ? C13 C12 C17 C16 -1.05(19) . . . . ? C13 C14 C15 C16 -1.4(2) . . . . ? C13 C14 C15 C18 177.69(13) . . . . ? C14 C15 C16 C17 1.51(19) . . . . ? C15 C16 C17 C12 -0.33(19) . . . . ? C17 C12 C13 C14 1.18(19) . . . . ? C18 C15 C16 C17 -177.54(12) . . . . ? C19 C2 C3 O3 106.68(11) . . . . ? C19 C20 C21 C22 -0.29(19) . . . . ? C20 C19 C24 C23 -0.1(2) . . . . ? C20 C21 C22 C23 -0.6(2) . . . . ? C20 C21 C22 C25 179.31(12) . . . . ? C21 C22 C23 C24 1.1(2) . . . . ? C22 C23 C24 C19 -0.8(2) . . . . ? C24 C19 C20 C21 0.63(19) . . . . ? C25 C22 C23 C24 -178.77(13) . . . . ?