#------------------------------------------------------------------------------ #$Date: 2020-05-13 02:17:31 +0300 (Wed, 13 May 2020) $ #$Revision: 251992 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038347.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_4038347 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 'C23 H29 Br N2 O3 S' _chemical_formula_sum 'C23 H29 Br N2 O3 S' _chemical_formula_weight 493.45 _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 2019-12-03 _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 101.628(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.7711(8) _cell_length_b 11.4910(7) _cell_length_c 16.0665(10) _cell_measurement_reflns_used 9901 _cell_measurement_temperature 120 _cell_measurement_theta_max 32.41 _cell_measurement_theta_min 2.19 _cell_volume 2309.4(2) _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 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device '3-circle area detector diffractometer' _diffrn_measurement_device_type 'Bruker D8 Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'focusing mirrors' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_unetI/netI 0.0274 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 58322 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 32.573 _diffrn_reflns_theta_min 2.195 _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 1.897 _exptl_absorpt_correction_T_max 0.8222 _exptl_absorpt_correction_T_min 0.5586 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker, 2016) was used for absorption correction. wR2(int) was 0.1355 before and 0.0489 after correction. The Ratio of minimum to maximum transmission is 0.6794. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.419 _exptl_crystal_description irregular _exptl_crystal_F_000 1024 _exptl_crystal_size_max 0.436 _exptl_crystal_size_mid 0.272 _exptl_crystal_size_min 0.164 _refine_diff_density_max 0.633 _refine_diff_density_min -0.558 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 287 _refine_ls_number_reflns 8408 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0306 _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^)+(0.0461P)^2^+0.5405P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0798 _refine_ls_wR_factor_ref 0.0844 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6805 _reflns_number_total 8408 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 19srv354.cif _cod_data_source_block 19srv354 _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 4038347 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Others Uiso(H23A)=Uiso(H23B)=Uiso(H23C)=FVAR(1) Uiso(H16A)=Uiso(H16B)=Uiso(H16C)=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) 3.b Aromatic/amide H refined with riding coordinates: C11(H11), C12(H12), C14(H14), C15(H15), C18(H18), C19(H19), C21(H21), C22(H22) 3.c Idealised Me refined as rotating group: C16(H16A,H16B,H16C), C23(H23A,H23B,H23C) ; _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 0.492 _shelx_estimated_absorpt_t_max 0.746 _shelx_res_checksum 65486 _shelx_res_file ; TITL 19srv354_a.res in P2(1)/n 19srv354.res created by SHELXL-2018/3 at 19:12:59 on 03-Dec-2019 REM Old TITL 19srv354 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.115, Rweak 0.006, Alpha 0.028 REM 0.483 for 249 systematic absences, Orientation as input REM Formula found by SHELXT: C23 N2 O3 S Br CELL 0.71073 12.7711 11.491 16.0665 90 101.628 90 ZERR 4 0.0008 0.0007 0.001 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Br N O S UNIT 92 116 4 8 12 4 EQIV $1 1-X,1-Y,1-Z L.S. 7 PLAN 6 SIZE 0.164 0.272 0.436 TEMP -153.15 CONF HTAB N1 N2_$1 BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.046100 0.540500 FVAR 0.48803 0.05636 0.07476 BR 3 0.234354 -0.059487 0.456040 11.00000 0.02036 0.02252 = 0.03467 0.00698 0.00118 -0.00529 S 6 0.228682 0.465025 0.383778 11.00000 0.01445 0.01657 = 0.01914 -0.00082 0.00067 -0.00315 O1 5 0.214615 0.354194 0.420888 11.00000 0.02305 0.01571 = 0.04439 0.00295 0.00758 -0.00396 O2 5 0.205153 0.478636 0.293307 11.00000 0.02161 0.03336 = 0.01774 -0.00621 -0.00174 -0.00238 O3 5 0.507330 0.399567 0.273582 11.00000 0.02610 0.01478 = 0.01474 -0.00318 0.00108 0.00330 N1 4 0.352906 0.498955 0.417371 11.00000 0.01429 0.01588 = 0.01458 0.00209 0.00106 -0.00251 H1 2 0.372591 0.486117 0.466450 11.00000 0.02191 N2 4 0.564331 0.494975 0.397231 11.00000 0.01501 0.01172 = 0.01245 0.00178 0.00114 0.00036 C1 1 0.398484 0.605558 0.389243 11.00000 0.01558 0.01320 = 0.01530 -0.00084 0.00374 -0.00128 AFIX 23 H1A 2 0.424703 0.656009 0.439030 11.00000 -1.20000 H1B 2 0.342052 0.648543 0.349849 11.00000 -1.20000 AFIX 0 C2 1 0.491523 0.578394 0.344132 11.00000 0.01473 0.01158 = 0.01103 -0.00025 0.00107 0.00062 C3 1 0.452693 0.510449 0.259927 11.00000 0.02179 0.01448 = 0.01180 -0.00086 0.00148 0.00110 H3A 2 0.377022 0.496502 0.248306 11.00000 0.02283 H3B 2 0.469413 0.545846 0.210443 11.00000 0.02155 C4 1 0.566384 0.402506 0.353789 11.00000 0.01424 0.01391 = 0.01496 0.00130 0.00502 -0.00092 C5 1 0.628029 0.294003 0.380435 11.00000 0.01713 0.01355 = 0.02256 0.00107 0.00531 0.00221 AFIX 23 H5A 2 0.663510 0.300716 0.440989 11.00000 -1.20000 H5B 2 0.684423 0.285292 0.346688 11.00000 -1.20000 AFIX 0 C6 1 0.556922 0.185313 0.368592 11.00000 0.02106 0.01203 = 0.01937 -0.00142 0.00577 0.00083 AFIX 23 H6A 2 0.519565 0.180360 0.308400 11.00000 -1.20000 H6B 2 0.602679 0.115442 0.381438 11.00000 -1.20000 AFIX 0 C7 1 0.474020 0.184942 0.425042 11.00000 0.02133 0.01340 = 0.02286 -0.00405 0.00679 -0.00251 AFIX 23 H7A 2 0.511255 0.186598 0.485368 11.00000 -1.20000 H7B 2 0.429783 0.256144 0.413790 11.00000 -1.20000 AFIX 0 C8 1 0.401425 0.078474 0.409953 11.00000 0.02133 0.01578 = 0.02020 -0.00195 0.00363 -0.00348 AFIX 23 H8A 2 0.360464 0.078820 0.350667 11.00000 -1.20000 H8B 2 0.445315 0.006814 0.418517 11.00000 -1.20000 AFIX 0 C9 1 0.325218 0.079280 0.470536 11.00000 0.02130 0.01686 = 0.03219 -0.00043 0.00818 -0.00269 AFIX 23 H9A 2 0.279747 0.149681 0.460383 11.00000 -1.20000 H9B 2 0.366461 0.082443 0.529686 11.00000 -1.20000 AFIX 0 C10 1 0.149866 0.567305 0.425508 11.00000 0.01204 0.01885 = 0.01793 0.00215 0.00056 -0.00241 C11 1 0.104747 0.660648 0.376309 11.00000 0.01917 0.02284 = 0.01930 0.00492 0.00148 -0.00066 AFIX 43 H11 2 0.114042 0.668456 0.319379 11.00000 -1.20000 AFIX 0 C12 1 0.045870 0.742638 0.410873 11.00000 0.02039 0.01917 = 0.02995 0.00688 0.00435 0.00017 AFIX 43 H12 2 0.013501 0.805487 0.376694 11.00000 -1.20000 AFIX 0 C13 1 0.033564 0.734183 0.494679 11.00000 0.01657 0.02204 = 0.03120 -0.00067 0.00725 -0.00371 C14 1 0.078375 0.638695 0.542547 11.00000 0.02256 0.03343 = 0.02234 0.00383 0.00772 0.00006 AFIX 43 H14 2 0.069387 0.630813 0.599549 11.00000 -1.20000 AFIX 0 C15 1 0.135634 0.555293 0.508579 11.00000 0.01920 0.02883 = 0.02110 0.00818 0.00311 0.00219 AFIX 43 H15 2 0.165015 0.490287 0.541770 11.00000 -1.20000 AFIX 0 C16 1 -0.024539 0.826593 0.533667 11.00000 0.03035 0.02921 = 0.05124 -0.00587 0.01965 -0.00068 AFIX 137 H16A 2 -0.069980 0.871622 0.488550 11.00000 31.00000 H16B 2 0.027475 0.878494 0.568508 11.00000 31.00000 H16C 2 -0.069007 0.789929 0.569372 11.00000 31.00000 AFIX 0 C17 1 0.550309 0.689414 0.329704 11.00000 0.01566 0.01307 = 0.01254 -0.00008 0.00391 0.00074 C18 1 0.661386 0.696113 0.351662 11.00000 0.01617 0.01580 = 0.02231 0.00158 0.00455 0.00271 AFIX 43 H18 2 0.700650 0.632685 0.380398 11.00000 -1.20000 AFIX 0 C19 1 0.715653 0.793851 0.332275 11.00000 0.01566 0.02093 = 0.02791 -0.00068 0.00685 -0.00144 AFIX 43 H19 2 0.791514 0.795424 0.346987 11.00000 -1.20000 AFIX 0 C20 1 0.661201 0.889572 0.291730 11.00000 0.02371 0.01414 = 0.02046 -0.00275 0.01204 -0.00219 C21 1 0.550135 0.884189 0.271690 11.00000 0.02312 0.01328 = 0.02218 0.00379 0.00641 0.00164 AFIX 43 H21 2 0.510952 0.949017 0.245022 11.00000 -1.20000 AFIX 0 C22 1 0.495144 0.785757 0.289894 11.00000 0.01667 0.01587 = 0.02150 0.00381 0.00160 0.00082 AFIX 43 H22 2 0.419291 0.784172 0.275060 11.00000 -1.20000 AFIX 0 C23 1 0.720927 0.994567 0.269502 11.00000 0.03160 0.01698 = 0.04260 -0.00053 0.02123 -0.00456 AFIX 137 H23A 2 0.670650 1.048060 0.234530 11.00000 21.00000 H23B 2 0.775005 0.969732 0.237764 11.00000 21.00000 H23C 2 0.755933 1.034131 0.321769 11.00000 21.00000 AFIX 0 HKLF 4 REM 19srv354_a.res in P2(1)/n REM wR2 = 0.0844, GooF = S = 1.051, Restrained GooF = 1.051 for all data REM R1 = 0.0306 for 6805 Fo > 4sig(Fo) and 0.0450 for all 8408 data REM 287 parameters refined using 0 restraints END WGHT 0.0461 0.5405 REM Highest difference peak 0.633, deepest hole -0.558, 1-sigma level 0.066 Q1 1 0.2668 -0.0821 0.4197 11.00000 0.05 0.63 Q2 1 0.6038 0.8834 0.2823 11.00000 0.05 0.46 Q3 1 0.4436 0.5867 0.3639 11.00000 0.05 0.46 Q4 1 0.5196 0.1813 0.3988 11.00000 0.05 0.44 Q5 1 0.6035 0.6959 0.3430 11.00000 0.05 0.43 Q6 1 0.5243 0.8382 0.2807 11.00000 0.05 0.42 ; _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 Br Br 0.23435(2) -0.05949(2) 0.45604(2) 0.02646(5) Uani 1 1 d . . . . . S S 0.22868(2) 0.46502(3) 0.38378(2) 0.01710(6) Uani 1 1 d . . . . . O1 O 0.21461(8) 0.35419(9) 0.42089(7) 0.0276(2) Uani 1 1 d . . . . . O2 O 0.20515(8) 0.47864(10) 0.29331(6) 0.0250(2) Uani 1 1 d . . . . . O3 O 0.50733(8) 0.39957(8) 0.27358(5) 0.01896(18) Uani 1 1 d . . . . . N1 N 0.35291(8) 0.49895(9) 0.41737(7) 0.01518(19) Uani 1 1 d . . . . . H1 H 0.3726(14) 0.4861(16) 0.4665(12) 0.022(4) Uiso 1 1 d . . . . . N2 N 0.56433(8) 0.49498(9) 0.39723(6) 0.01329(18) Uani 1 1 d . . . . . C1 C 0.39848(9) 0.60556(10) 0.38924(7) 0.0146(2) Uani 1 1 d . . . . . H1A H 0.424703 0.656009 0.439030 0.018 Uiso 1 1 calc R U . . . H1B H 0.342052 0.648543 0.349849 0.018 Uiso 1 1 calc R U . . . C2 C 0.49152(9) 0.57839(10) 0.34413(7) 0.0127(2) Uani 1 1 d . . . . . C3 C 0.45269(10) 0.51045(11) 0.25993(7) 0.0163(2) Uani 1 1 d . . . . . H3A H 0.3770(14) 0.4965(16) 0.2483(11) 0.023(4) Uiso 1 1 d . . . . . H3B H 0.4694(14) 0.5458(14) 0.2104(11) 0.022(4) Uiso 1 1 d . . . . . C4 C 0.56638(9) 0.40251(10) 0.35379(7) 0.0141(2) Uani 1 1 d . . . . . C5 C 0.62803(10) 0.29400(10) 0.38043(8) 0.0176(2) Uani 1 1 d . . . . . H5A H 0.663510 0.300716 0.440989 0.021 Uiso 1 1 calc R U . . . H5B H 0.684423 0.285292 0.346688 0.021 Uiso 1 1 calc R U . . . C6 C 0.55692(10) 0.18531(10) 0.36859(8) 0.0173(2) Uani 1 1 d . . . . . H6A H 0.519565 0.180360 0.308400 0.021 Uiso 1 1 calc R U . . . H6B H 0.602679 0.115442 0.381438 0.021 Uiso 1 1 calc R U . . . C7 C 0.47402(10) 0.18494(11) 0.42504(8) 0.0189(2) Uani 1 1 d . . . . . H7A H 0.511255 0.186598 0.485368 0.023 Uiso 1 1 calc R U . . . H7B H 0.429783 0.256144 0.413790 0.023 Uiso 1 1 calc R U . . . C8 C 0.40142(11) 0.07847(11) 0.40995(8) 0.0192(2) Uani 1 1 d . . . . . H8A H 0.360464 0.078820 0.350667 0.023 Uiso 1 1 calc R U . . . H8B H 0.445315 0.006814 0.418517 0.023 Uiso 1 1 calc R U . . . C9 C 0.32522(11) 0.07928(12) 0.47054(10) 0.0231(3) Uani 1 1 d . . . . . H9A H 0.279747 0.149681 0.460383 0.028 Uiso 1 1 calc R U . . . H9B H 0.366461 0.082443 0.529686 0.028 Uiso 1 1 calc R U . . . C10 C 0.14987(10) 0.56730(11) 0.42551(8) 0.0166(2) Uani 1 1 d . . . . . C11 C 0.10475(10) 0.66065(12) 0.37631(8) 0.0208(2) Uani 1 1 d . . . . . H11 H 0.114042 0.668456 0.319379 0.025 Uiso 1 1 calc R U . . . C12 C 0.04587(11) 0.74264(12) 0.41087(9) 0.0233(3) Uani 1 1 d . . . . . H12 H 0.013501 0.805487 0.376694 0.028 Uiso 1 1 calc R U . . . C13 C 0.03356(10) 0.73418(12) 0.49468(9) 0.0229(3) Uani 1 1 d . . . . . C14 C 0.07837(11) 0.63869(14) 0.54255(9) 0.0257(3) Uani 1 1 d . . . . . H14 H 0.069387 0.630813 0.599549 0.031 Uiso 1 1 calc R U . . . C15 C 0.13563(11) 0.55529(12) 0.50858(9) 0.0232(3) Uani 1 1 d . . . . . H15 H 0.165015 0.490287 0.541770 0.028 Uiso 1 1 calc R U . . . C16 C -0.02454(13) 0.82659(15) 0.53367(12) 0.0353(4) Uani 1 1 d . . . . . H16A H -0.069980 0.871622 0.488550 0.075(5) Uiso 1 1 calc R U . . . H16B H 0.027475 0.878494 0.568508 0.075(5) Uiso 1 1 calc R U . . . H16C H -0.069007 0.789929 0.569372 0.075(5) Uiso 1 1 calc R U . . . C17 C 0.55031(9) 0.68941(10) 0.32970(7) 0.0136(2) Uani 1 1 d . . . . . C18 C 0.66139(10) 0.69611(11) 0.35166(8) 0.0180(2) Uani 1 1 d . . . . . H18 H 0.700650 0.632685 0.380398 0.022 Uiso 1 1 calc R U . . . C19 C 0.71565(10) 0.79385(12) 0.33227(9) 0.0212(2) Uani 1 1 d . . . . . H19 H 0.791514 0.795424 0.346987 0.025 Uiso 1 1 calc R U . . . C20 C 0.66120(11) 0.88957(11) 0.29173(8) 0.0184(2) Uani 1 1 d . . . . . C21 C 0.55013(11) 0.88419(11) 0.27169(8) 0.0193(2) Uani 1 1 d . . . . . H21 H 0.510952 0.949017 0.245022 0.023 Uiso 1 1 calc R U . . . C22 C 0.49514(10) 0.78576(11) 0.28989(8) 0.0183(2) Uani 1 1 d . . . . . H22 H 0.419291 0.784172 0.275060 0.022 Uiso 1 1 calc R U . . . C23 C 0.72093(13) 0.99457(12) 0.26950(11) 0.0285(3) Uani 1 1 d . . . . . H23A H 0.670650 1.048060 0.234530 0.056(4) Uiso 1 1 calc R U . . . H23B H 0.775005 0.969732 0.237764 0.056(4) Uiso 1 1 calc R U . . . H23C H 0.755933 1.034131 0.321769 0.056(4) Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.02036(7) 0.02252(7) 0.03467(9) 0.00698(5) 0.00118(5) -0.00529(5) S 0.01445(13) 0.01657(14) 0.01914(14) -0.00082(10) 0.00067(10) -0.00315(10) O1 0.0230(5) 0.0157(5) 0.0444(6) 0.0029(4) 0.0076(4) -0.0040(4) O2 0.0216(5) 0.0334(5) 0.0177(4) -0.0062(4) -0.0017(4) -0.0024(4) O3 0.0261(5) 0.0148(4) 0.0147(4) -0.0032(3) 0.0011(3) 0.0033(3) N1 0.0143(4) 0.0159(5) 0.0146(5) 0.0021(4) 0.0011(4) -0.0025(4) N2 0.0150(4) 0.0117(4) 0.0125(4) 0.0018(3) 0.0011(3) 0.0004(3) C1 0.0156(5) 0.0132(5) 0.0153(5) -0.0008(4) 0.0037(4) -0.0013(4) C2 0.0147(5) 0.0116(5) 0.0110(5) -0.0002(4) 0.0011(4) 0.0006(4) C3 0.0218(6) 0.0145(5) 0.0118(5) -0.0009(4) 0.0015(4) 0.0011(4) C4 0.0142(5) 0.0139(5) 0.0150(5) 0.0013(4) 0.0050(4) -0.0009(4) C5 0.0171(5) 0.0136(5) 0.0226(6) 0.0011(4) 0.0053(4) 0.0022(4) C6 0.0211(6) 0.0120(5) 0.0194(6) -0.0014(4) 0.0058(4) 0.0008(4) C7 0.0213(6) 0.0134(5) 0.0229(6) -0.0040(4) 0.0068(5) -0.0025(4) C8 0.0213(6) 0.0158(5) 0.0202(6) -0.0019(4) 0.0036(5) -0.0035(4) C9 0.0213(6) 0.0169(6) 0.0322(7) -0.0004(5) 0.0082(5) -0.0027(5) C10 0.0120(5) 0.0189(6) 0.0179(5) 0.0022(4) 0.0006(4) -0.0024(4) C11 0.0192(6) 0.0228(6) 0.0193(6) 0.0049(5) 0.0015(5) -0.0007(5) C12 0.0204(6) 0.0192(6) 0.0300(7) 0.0069(5) 0.0043(5) 0.0002(5) C13 0.0166(5) 0.0220(6) 0.0312(7) -0.0007(5) 0.0073(5) -0.0037(5) C14 0.0226(6) 0.0334(8) 0.0223(6) 0.0038(5) 0.0077(5) 0.0001(5) C15 0.0192(6) 0.0288(7) 0.0211(6) 0.0082(5) 0.0031(5) 0.0022(5) C16 0.0304(8) 0.0292(8) 0.0512(10) -0.0059(7) 0.0196(7) -0.0007(6) C17 0.0157(5) 0.0131(5) 0.0125(5) -0.0001(4) 0.0039(4) 0.0007(4) C18 0.0162(5) 0.0158(5) 0.0223(6) 0.0016(4) 0.0046(4) 0.0027(4) C19 0.0157(5) 0.0209(6) 0.0279(7) -0.0007(5) 0.0069(5) -0.0014(4) C20 0.0237(6) 0.0141(5) 0.0205(6) -0.0027(4) 0.0120(5) -0.0022(4) C21 0.0231(6) 0.0133(5) 0.0222(6) 0.0038(4) 0.0064(5) 0.0016(4) C22 0.0167(5) 0.0159(5) 0.0215(6) 0.0038(4) 0.0016(4) 0.0008(4) C23 0.0316(7) 0.0170(6) 0.0426(9) -0.0005(6) 0.0212(6) -0.0046(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' Br Br -0.2901 2.4595 '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 0.1050 1.00 0.00 1.00 0.1480 -2.00 -1.00 2.00 0.1100 3.00 0.00 -2.00 0.0540 -1.00 0.00 1.00 0.0820 -2.00 -3.00 3.00 0.1430 1.00 2.00 -2.00 0.1540 -2.00 1.00 -3.00 0.1210 3.00 1.00 1.00 0.0730 -3.00 0.00 -2.00 0.0960 2.00 1.00 -3.00 0.0790 -1.00 -1.00 -3.00 0.1190 1.00 -1.00 -2.00 0.1420 -2.00 1.00 2.00 0.1350 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 105.80(6) . . ? O1 S C10 107.75(6) . . ? O2 S O1 120.07(7) . . ? O2 S N1 107.66(6) . . ? O2 S C10 107.08(6) . . ? N1 S C10 107.99(6) . . ? C4 O3 C3 106.31(9) . . ? S N1 H1 112.4(13) . . ? C1 N1 S 121.49(8) . . ? C1 N1 H1 113.4(13) . . ? C4 N2 C2 107.71(10) . . ? N1 C1 H1A 109.3 . . ? N1 C1 H1B 109.3 . . ? N1 C1 C2 111.52(10) . . ? H1A C1 H1B 108.0 . . ? C2 C1 H1A 109.3 . . ? C2 C1 H1B 109.3 . . ? N2 C2 C1 108.30(9) . . ? N2 C2 C3 103.27(9) . . ? N2 C2 C17 111.03(9) . . ? C1 C2 C3 111.69(10) . . ? C17 C2 C1 110.62(9) . . ? C17 C2 C3 111.67(9) . . ? O3 C3 C2 104.52(9) . . ? O3 C3 H3A 108.5(11) . . ? O3 C3 H3B 108.6(10) . . ? C2 C3 H3A 112.7(10) . . ? C2 C3 H3B 115.2(10) . . ? H3A C3 H3B 107.1(14) . . ? O3 C4 C5 114.36(10) . . ? N2 C4 O3 118.18(11) . . ? N2 C4 C5 127.45(11) . . ? C4 C5 H5A 109.1 . . ? C4 C5 H5B 109.1 . . ? C4 C5 C6 112.36(10) . . ? H5A C5 H5B 107.9 . . ? C6 C5 H5A 109.1 . . ? C6 C5 H5B 109.1 . . ? C5 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C7 C6 C5 113.13(10) . . ? C7 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? C6 C7 H7A 109.1 . . ? C6 C7 H7B 109.1 . . ? H7A C7 H7B 107.9 . . ? C8 C7 C6 112.34(10) . . ? C8 C7 H7A 109.1 . . ? C8 C7 H7B 109.1 . . ? C7 C8 H8A 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.2 . . ? C9 C8 C7 110.07(11) . . ? C9 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? Br C9 H9A 109.4 . . ? Br C9 H9B 109.4 . . ? C8 C9 Br 111.23(9) . . ? C8 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? H9A C9 H9B 108.0 . . ? C11 C10 S 120.11(10) . . ? C11 C10 C15 120.29(12) . . ? C15 C10 S 119.58(10) . . ? C10 C11 H11 120.2 . . ? C10 C11 C12 119.53(12) . . ? C12 C11 H11 120.2 . . ? C11 C12 H12 119.5 . . ? C11 C12 C13 121.05(12) . . ? C13 C12 H12 119.5 . . ? C12 C13 C14 118.37(13) . . ? C12 C13 C16 121.07(13) . . ? C14 C13 C16 120.55(14) . . ? C13 C14 H14 119.4 . . ? C15 C14 C13 121.23(13) . . ? C15 C14 H14 119.4 . . ? C10 C15 H15 120.3 . . ? C14 C15 C10 119.48(12) . . ? C14 C15 H15 120.3 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C2 121.08(11) . . ? C18 C17 C22 117.79(11) . . ? C22 C17 C2 121.04(11) . . ? C17 C18 H18 119.4 . . ? C19 C18 C17 121.13(12) . . ? C19 C18 H18 119.4 . . ? C18 C19 H19 119.3 . . ? C18 C19 C20 121.33(12) . . ? C20 C19 H19 119.3 . . ? C19 C20 C21 117.60(11) . . ? C19 C20 C23 120.96(12) . . ? C21 C20 C23 121.43(12) . . ? C20 C21 H21 119.3 . . ? C20 C21 C22 121.41(12) . . ? C22 C21 H21 119.3 . . ? C17 C22 H22 119.6 . . ? C21 C22 C17 120.71(12) . . ? C21 C22 H22 119.6 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23B 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 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 Br C9 1.9582(13) . ? S O1 1.4328(10) . ? S O2 1.4323(10) . ? S N1 1.6171(11) . ? S C10 1.7652(13) . ? O3 C3 1.4480(15) . ? O3 C4 1.3560(15) . ? N1 H1 0.792(18) . ? N1 C1 1.4662(15) . ? N2 C2 1.4804(15) . ? N2 C4 1.2745(15) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C1 C2 1.5433(16) . ? C2 C3 1.5541(16) . ? C2 C17 1.5215(16) . ? C3 H3A 0.960(17) . ? C3 H3B 0.955(18) . ? C4 C5 1.4905(17) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.5333(17) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.5266(17) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.5246(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.5088(19) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.3870(17) . ? C10 C15 1.3897(18) . ? C11 H11 0.9500 . ? C11 C12 1.3892(19) . ? C12 H12 0.9500 . ? C12 C13 1.390(2) . ? C13 C14 1.395(2) . ? C13 C16 1.503(2) . ? C14 H14 0.9500 . ? C14 C15 1.383(2) . ? C15 H15 0.9500 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.3932(17) . ? C17 C22 1.3962(17) . ? C18 H18 0.9500 . ? C18 C19 1.3877(18) . ? C19 H19 0.9500 . ? C19 C20 1.3911(19) . ? C20 C21 1.3912(18) . ? C20 C23 1.5082(18) . ? C21 H21 0.9500 . ? C21 C22 1.3932(17) . ? C22 H22 0.9500 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? 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 0.792(18) 2.187(18) 2.9539(15) 163.3(18) 3_666 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 C1 C2 -120.22(10) . . . . ? S C10 C11 C12 -177.86(10) . . . . ? S C10 C15 C14 176.76(11) . . . . ? O1 S N1 C1 177.19(10) . . . . ? O1 S C10 C11 -148.05(10) . . . . ? O1 S C10 C15 33.58(12) . . . . ? O2 S N1 C1 47.65(11) . . . . ? O2 S C10 C11 -17.60(12) . . . . ? O2 S C10 C15 164.03(10) . . . . ? O3 C4 C5 C6 -53.83(14) . . . . ? N1 S C10 C11 98.09(11) . . . . ? N1 S C10 C15 -80.28(11) . . . . ? N1 C1 C2 N2 -47.95(12) . . . . ? N1 C1 C2 C3 65.11(12) . . . . ? N1 C1 C2 C17 -169.84(9) . . . . ? N2 C2 C3 O3 -0.76(12) . . . . ? N2 C2 C17 C18 11.04(15) . . . . ? N2 C2 C17 C22 -172.42(11) . . . . ? N2 C4 C5 C6 126.69(13) . . . . ? C1 C2 C3 O3 -116.92(10) . . . . ? C1 C2 C17 C18 131.31(12) . . . . ? C1 C2 C17 C22 -52.15(14) . . . . ? C2 N2 C4 O3 0.78(14) . . . . ? C2 N2 C4 C5 -179.77(11) . . . . ? C2 C17 C18 C19 174.70(11) . . . . ? C2 C17 C22 C21 -175.60(11) . . . . ? C3 O3 C4 N2 -1.30(14) . . . . ? C3 O3 C4 C5 179.17(10) . . . . ? C3 C2 C17 C18 -103.63(13) . . . . ? C3 C2 C17 C22 72.92(14) . . . . ? C4 O3 C3 C2 1.16(12) . . . . ? C4 N2 C2 C1 118.61(10) . . . . ? C4 N2 C2 C3 0.06(12) . . . . ? C4 N2 C2 C17 -119.75(10) . . . . ? C4 C5 C6 C7 -64.52(14) . . . . ? C5 C6 C7 C8 177.85(11) . . . . ? C6 C7 C8 C9 176.95(11) . . . . ? C7 C8 C9 Br -177.77(9) . . . . ? C10 S N1 C1 -67.66(11) . . . . ? C10 C11 C12 C13 1.6(2) . . . . ? C11 C10 C15 C14 -1.6(2) . . . . ? C11 C12 C13 C14 -2.4(2) . . . . ? C11 C12 C13 C16 176.32(13) . . . . ? C12 C13 C14 C15 1.3(2) . . . . ? C13 C14 C15 C10 0.7(2) . . . . ? C15 C10 C11 C12 0.50(19) . . . . ? C16 C13 C14 C15 -177.46(14) . . . . ? C17 C2 C3 O3 118.61(10) . . . . ? C17 C18 C19 C20 1.3(2) . . . . ? C18 C17 C22 C21 1.06(19) . . . . ? C18 C19 C20 C21 0.4(2) . . . . ? C18 C19 C20 C23 -178.90(12) . . . . ? C19 C20 C21 C22 -1.26(19) . . . . ? C20 C21 C22 C17 0.5(2) . . . . ? C22 C17 C18 C19 -1.95(19) . . . . ? C23 C20 C21 C22 178.00(13) . . . . ?