#------------------------------------------------------------------------------ #$Date: 2020-05-13 02:18:37 +0300 (Wed, 13 May 2020) $ #$Revision: 251995 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038350.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_4038350 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 H22 Br Cl N2 O4 S' _chemical_formula_sum 'C25 H22 Br Cl N2 O4 S' _chemical_formula_weight 561.86 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2020-01-27 _audit_creation_method ; Olex2 1.3-alpha (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _cell_angle_alpha 81.001(2) _cell_angle_beta 89.408(2) _cell_angle_gamma 77.106(2) _cell_formula_units_Z 2 _cell_length_a 8.9040(5) _cell_length_b 11.4226(7) _cell_length_c 11.9517(7) _cell_measurement_reflns_used 8940 _cell_measurement_temperature 120 _cell_measurement_theta_max 30.02 _cell_measurement_theta_min 2.32 _cell_volume 1169.95(12) _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 0.0395 _diffrn_reflns_av_unetI/netI 0.0415 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 26308 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.137 _diffrn_reflns_theta_min 2.324 _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 1.997 _exptl_absorpt_correction_T_max 0.8879 _exptl_absorpt_correction_T_min 0.7738 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0980 before and 0.0401 after correction. The Ratio of minimum to maximum transmission is 0.8715. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.595 _exptl_crystal_description wedge _exptl_crystal_F_000 572 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.615 _refine_diff_density_min -0.616 _refine_diff_density_rms 0.078 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 313 _refine_ls_number_reflns 6888 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0563 _refine_ls_R_factor_gt 0.0374 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0515P)^2^+0.4968P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0955 _refine_ls_wR_factor_ref 0.1019 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5324 _reflns_number_total 6888 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file 20srv026.cif _cod_data_source_block 20srv026 _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 4038350 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2. Restrained distances N1-H1 0.88 with sigma of 0.02 3. Others Uiso(H7A)=Uiso(H7B)=Uiso(H7C)=FVAR(1) 4.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C10(H10A,H10B), C25(H25A,H25B) 4.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23) 4.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_res_checksum 52948 _shelx_res_file ; TITL 20srv026_a.res in P-1 20srv026.res created by SHELXL-2018/3 at 00:26:45 on 27-Jan-2020 REM Old TITL 20srv026 in P-1 REM SHELXT solution in P-1: R1 0.148, Rweak 0.010, Alpha 0.044 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C25 N2 O4 Cl2 Br CELL 0.71073 8.904 11.4226 11.9517 81.001 89.4079 77.1061 ZERR 2 0.0005 0.0007 0.0007 0.0022 0.0024 0.0023 LATT 1 SFAC C H Br Cl N O S UNIT 50 44 2 2 4 8 2 EQIV $1 2-X,1-Y,1-Z DFIX 0.88 N1 H1 L.S. 7 PLAN 1 TEMP -153.15 CONF HTAB N1 O1_$1 BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.051500 0.496800 FVAR 0.18684 0.05530 BR 3 0.892210 1.309006 0.078403 11.00000 0.02934 0.04351 = 0.02776 0.01344 -0.00338 -0.01501 CL 4 0.243378 0.312995 0.887246 11.00000 0.04344 0.04824 = 0.02734 0.00555 0.00272 -0.03438 S 7 0.935894 0.347180 0.578329 11.00000 0.01840 0.01150 = 0.01488 -0.00235 0.00320 -0.00594 O1 6 1.093105 0.346076 0.606141 11.00000 0.01833 0.01772 = 0.02306 -0.00265 0.00503 -0.00652 O2 6 0.902687 0.324787 0.466838 11.00000 0.03333 0.01741 = 0.01558 -0.00491 0.00325 -0.01070 O3 6 0.753162 0.807982 0.711579 11.00000 0.02285 0.01698 = 0.01700 -0.00367 0.00071 -0.00929 O4 6 0.648451 1.170467 0.143014 11.00000 0.02656 0.02721 = 0.02273 0.00173 -0.00575 -0.00982 N1 5 0.819201 0.474192 0.592629 11.00000 0.02201 0.01087 = 0.01325 -0.00004 -0.00016 -0.00396 H1 2 0.802227 0.520805 0.533931 11.00000 0.02069 N2 5 0.643969 0.702740 0.602182 11.00000 0.01494 0.01354 = 0.01460 -0.00045 0.00092 -0.00393 C1 1 0.873915 0.242366 0.682631 11.00000 0.01966 0.01048 = 0.01565 -0.00189 0.00334 -0.00644 C2 1 0.718147 0.242878 0.690458 11.00000 0.01957 0.01539 = 0.02587 -0.00097 -0.00220 -0.00630 AFIX 43 H2 2 0.644708 0.299913 0.640691 11.00000 -1.20000 AFIX 0 C3 1 0.671386 0.158857 0.772038 11.00000 0.02310 0.01875 = 0.02660 -0.00512 0.00480 -0.01139 AFIX 43 H3 2 0.564724 0.159895 0.778904 11.00000 -1.20000 AFIX 0 C4 1 0.777604 0.073104 0.843997 11.00000 0.03133 0.01588 = 0.01665 -0.00502 0.00525 -0.01261 C5 1 0.932933 0.074010 0.833715 11.00000 0.02805 0.01771 = 0.02143 0.00217 -0.00104 -0.00419 AFIX 43 H5 2 1.006753 0.015480 0.881950 11.00000 -1.20000 AFIX 0 C6 1 0.982454 0.159179 0.753965 11.00000 0.01930 0.01923 = 0.02141 -0.00177 0.00239 -0.00537 AFIX 43 H6 2 1.088709 0.160150 0.748635 11.00000 -1.20000 AFIX 0 C7 1 0.724015 -0.016588 0.932694 11.00000 0.04179 0.02517 = 0.02197 0.00040 0.00566 -0.01755 AFIX 137 H7A 2 0.810539 -0.085183 0.958042 11.00000 21.00000 H7B 2 0.641643 -0.046328 0.900399 11.00000 21.00000 H7C 2 0.685001 0.023396 0.997347 11.00000 21.00000 AFIX 0 C8 1 0.842740 0.533167 0.689516 11.00000 0.01606 0.01434 = 0.01636 -0.00369 0.00105 -0.00493 AFIX 23 H8A 2 0.924368 0.579308 0.673144 11.00000 -1.20000 H8B 2 0.875175 0.471138 0.757563 11.00000 -1.20000 AFIX 0 C9 1 0.689651 0.619869 0.710713 11.00000 0.01518 0.01454 = 0.01433 -0.00131 0.00095 -0.00601 C10 1 0.718997 0.706933 0.789788 11.00000 0.02053 0.01694 = 0.01591 -0.00162 0.00054 -0.00792 AFIX 23 H10A 2 0.626678 0.733963 0.834079 11.00000 -1.20000 H10B 2 0.807226 0.667973 0.842610 11.00000 -1.20000 AFIX 0 C11 1 0.571081 0.548116 0.753262 11.00000 0.01701 0.01375 = 0.01515 -0.00235 0.00255 -0.00568 C12 1 0.595793 0.476097 0.859154 11.00000 0.02217 0.02392 = 0.01330 -0.00106 -0.00080 -0.00946 AFIX 43 H12 2 0.682640 0.477322 0.904100 11.00000 -1.20000 AFIX 0 C13 1 0.497186 0.402547 0.900958 11.00000 0.02789 0.02326 = 0.01370 0.00110 0.00185 -0.01104 AFIX 43 H13 2 0.516098 0.352772 0.973129 11.00000 -1.20000 AFIX 0 C14 1 0.369909 0.403552 0.834485 11.00000 0.02469 0.02355 = 0.01927 -0.00126 0.00542 -0.01486 C15 1 0.342017 0.473675 0.729125 11.00000 0.02115 0.02847 = 0.02102 0.00053 -0.00228 -0.01344 AFIX 43 H15 2 0.254578 0.472604 0.684743 11.00000 -1.20000 AFIX 0 C16 1 0.443695 0.546504 0.688085 11.00000 0.01967 0.02148 = 0.01706 0.00299 -0.00065 -0.00855 AFIX 43 H16 2 0.425571 0.595091 0.615310 11.00000 -1.20000 AFIX 0 C17 1 0.692691 0.798029 0.609477 11.00000 0.01274 0.01519 = 0.01670 -0.00372 0.00161 -0.00295 C18 1 0.696908 0.896452 0.515944 11.00000 0.01438 0.01179 = 0.02098 -0.00445 0.00261 -0.00210 C19 1 0.776375 0.986463 0.525985 11.00000 0.02282 0.01695 = 0.01876 -0.00411 -0.00091 -0.00726 AFIX 43 H19 2 0.822996 0.988406 0.596610 11.00000 -1.20000 AFIX 0 C20 1 0.787667 1.073274 0.433208 11.00000 0.02425 0.01451 = 0.02179 -0.00476 0.00045 -0.00852 AFIX 43 H20 2 0.843641 1.133671 0.439946 11.00000 -1.20000 AFIX 0 C21 1 0.716897 1.072023 0.329942 11.00000 0.01524 0.01287 = 0.02056 -0.00251 0.00031 -0.00097 C22 1 0.632592 0.984301 0.321490 11.00000 0.01810 0.01840 = 0.02393 -0.00198 -0.00393 -0.00655 AFIX 43 H22 2 0.580611 0.985319 0.252209 11.00000 -1.20000 AFIX 0 C23 1 0.624133 0.896220 0.412815 11.00000 0.01710 0.01663 = 0.02575 -0.00160 -0.00282 -0.00668 AFIX 43 H23 2 0.568957 0.835402 0.405774 11.00000 -1.20000 AFIX 0 C24 1 0.732788 1.157823 0.225195 11.00000 0.01934 0.01456 = 0.01996 -0.00306 0.00140 -0.00308 C25 1 0.861596 1.224692 0.226082 11.00000 0.02442 0.02274 = 0.01945 0.00378 -0.00116 -0.01147 AFIX 23 H25A 2 0.958320 1.165725 0.253395 11.00000 -1.20000 H25B 2 0.836952 1.283958 0.279503 11.00000 -1.20000 AFIX 0 HKLF 4 REM 20srv026_a.res in P-1 REM wR2 = 0.1019, GooF = S = 1.063, Restrained GooF = 1.064 for all data REM R1 = 0.0374 for 5324 Fo > 4sig(Fo) and 0.0563 for all 6888 data REM 313 parameters refined using 1 restraints END WGHT 0.0512 0.5113 REM Highest difference peak 0.615, deepest hole -0.616, 1-sigma level 0.078 Q1 1 1.0210 0.3279 0.6000 11.00000 0.05 0.62 ; _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' 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 0.89221(3) 1.30901(2) 0.07840(2) 0.03452(9) Uani 1 1 d . . . . . Cl Cl 0.24338(8) 0.31299(6) 0.88725(5) 0.03713(16) Uani 1 1 d . . . . . S S 0.93589(5) 0.34718(4) 0.57833(4) 0.01451(10) Uani 1 1 d . . . . . O1 O 1.09311(16) 0.34608(12) 0.60614(12) 0.0194(3) Uani 1 1 d . . . . . O2 O 0.90269(18) 0.32479(13) 0.46684(12) 0.0211(3) Uani 1 1 d . . . . . O3 O 0.75316(16) 0.80798(12) 0.71158(12) 0.0181(3) Uani 1 1 d . . . . . O4 O 0.64845(18) 1.17047(14) 0.14301(13) 0.0255(3) Uani 1 1 d . . . . . N1 N 0.8192(2) 0.47419(14) 0.59263(14) 0.0155(3) Uani 1 1 d D . . . . H1 H 0.802(3) 0.5208(19) 0.5339(16) 0.021(6) Uiso 1 1 d D . . . . N2 N 0.64397(18) 0.70274(14) 0.60218(13) 0.0144(3) Uani 1 1 d . . . . . C1 C 0.8739(2) 0.24237(16) 0.68263(16) 0.0148(4) Uani 1 1 d . . . . . C2 C 0.7181(2) 0.24288(18) 0.69046(18) 0.0201(4) Uani 1 1 d . . . . . H2 H 0.644708 0.299913 0.640691 0.024 Uiso 1 1 calc R U . . . C3 C 0.6714(3) 0.15886(18) 0.77204(18) 0.0216(4) Uani 1 1 d . . . . . H3 H 0.564724 0.159895 0.778904 0.026 Uiso 1 1 calc R U . . . C4 C 0.7776(3) 0.07310(18) 0.84400(17) 0.0199(4) Uani 1 1 d . . . . . C5 C 0.9329(3) 0.07401(19) 0.83372(18) 0.0231(4) Uani 1 1 d . . . . . H5 H 1.006753 0.015480 0.881950 0.028 Uiso 1 1 calc R U . . . C6 C 0.9825(2) 0.15918(18) 0.75396(17) 0.0200(4) Uani 1 1 d . . . . . H6 H 1.088709 0.160150 0.748635 0.024 Uiso 1 1 calc R U . . . C7 C 0.7240(3) -0.0166(2) 0.93269(19) 0.0285(5) Uani 1 1 d . . . . . H7A H 0.810539 -0.085183 0.958042 0.055(6) Uiso 1 1 calc R U . . . H7B H 0.641643 -0.046328 0.900399 0.055(6) Uiso 1 1 calc R U . . . H7C H 0.685001 0.023396 0.997347 0.055(6) Uiso 1 1 calc R U . . . C8 C 0.8427(2) 0.53317(17) 0.68952(16) 0.0152(4) Uani 1 1 d . . . . . H8A H 0.924368 0.579308 0.673144 0.018 Uiso 1 1 calc R U . . . H8B H 0.875175 0.471138 0.757563 0.018 Uiso 1 1 calc R U . . . C9 C 0.6897(2) 0.61987(17) 0.71071(16) 0.0144(3) Uani 1 1 d . . . . . C10 C 0.7190(2) 0.70693(17) 0.78979(16) 0.0173(4) Uani 1 1 d . . . . . H10A H 0.626678 0.733963 0.834079 0.021 Uiso 1 1 calc R U . . . H10B H 0.807226 0.667973 0.842610 0.021 Uiso 1 1 calc R U . . . C11 C 0.5711(2) 0.54812(17) 0.75326(16) 0.0150(4) Uani 1 1 d . . . . . C12 C 0.5958(2) 0.47610(19) 0.85915(16) 0.0193(4) Uani 1 1 d . . . . . H12 H 0.682640 0.477322 0.904100 0.023 Uiso 1 1 calc R U . . . C13 C 0.4972(3) 0.40255(19) 0.90096(17) 0.0212(4) Uani 1 1 d . . . . . H13 H 0.516098 0.352772 0.973129 0.025 Uiso 1 1 calc R U . . . C14 C 0.3699(2) 0.40355(19) 0.83449(17) 0.0213(4) Uani 1 1 d . . . . . C15 C 0.3420(2) 0.4737(2) 0.72913(18) 0.0228(4) Uani 1 1 d . . . . . H15 H 0.254578 0.472604 0.684743 0.027 Uiso 1 1 calc R U . . . C16 C 0.4437(2) 0.54650(19) 0.68809(17) 0.0194(4) Uani 1 1 d . . . . . H16 H 0.425571 0.595091 0.615310 0.023 Uiso 1 1 calc R U . . . C17 C 0.6927(2) 0.79803(17) 0.60948(16) 0.0148(4) Uani 1 1 d . . . . . C18 C 0.6969(2) 0.89645(16) 0.51594(17) 0.0157(4) Uani 1 1 d . . . . . C19 C 0.7764(2) 0.98646(18) 0.52599(17) 0.0189(4) Uani 1 1 d . . . . . H19 H 0.822996 0.988406 0.596610 0.023 Uiso 1 1 calc R U . . . C20 C 0.7877(2) 1.07327(18) 0.43321(17) 0.0193(4) Uani 1 1 d . . . . . H20 H 0.843641 1.133671 0.439946 0.023 Uiso 1 1 calc R U . . . C21 C 0.7169(2) 1.07202(17) 0.32994(17) 0.0166(4) Uani 1 1 d . . . . . C22 C 0.6326(2) 0.98430(18) 0.32149(18) 0.0199(4) Uani 1 1 d . . . . . H22 H 0.580611 0.985319 0.252209 0.024 Uiso 1 1 calc R U . . . C23 C 0.6241(2) 0.89622(18) 0.41281(18) 0.0195(4) Uani 1 1 d . . . . . H23 H 0.568957 0.835402 0.405774 0.023 Uiso 1 1 calc R U . . . C24 C 0.7328(2) 1.15782(17) 0.22519(17) 0.0180(4) Uani 1 1 d . . . . . C25 C 0.8616(3) 1.22469(19) 0.22608(18) 0.0220(4) Uani 1 1 d . . . . . H25A H 0.958320 1.165725 0.253395 0.026 Uiso 1 1 calc R U . . . H25B H 0.836952 1.283958 0.279503 0.026 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 0.02934(14) 0.04351(15) 0.02776(13) 0.01344(10) -0.00338(9) -0.01501(11) Cl 0.0434(4) 0.0482(4) 0.0273(3) 0.0055(3) 0.0027(2) -0.0344(3) S 0.0184(2) 0.0115(2) 0.0149(2) -0.00235(16) 0.00320(17) -0.00594(17) O1 0.0183(7) 0.0177(7) 0.0231(7) -0.0026(6) 0.0050(6) -0.0065(6) O2 0.0333(8) 0.0174(7) 0.0156(7) -0.0049(5) 0.0033(6) -0.0107(6) O3 0.0229(7) 0.0170(6) 0.0170(7) -0.0037(5) 0.0007(5) -0.0093(6) O4 0.0266(8) 0.0272(8) 0.0227(8) 0.0017(6) -0.0058(6) -0.0098(6) N1 0.0220(8) 0.0109(7) 0.0132(8) 0.0000(6) -0.0002(6) -0.0040(6) N2 0.0149(8) 0.0135(7) 0.0146(7) -0.0004(6) 0.0009(6) -0.0039(6) C1 0.0197(9) 0.0105(8) 0.0156(9) -0.0019(7) 0.0033(7) -0.0064(7) C2 0.0196(10) 0.0154(9) 0.0259(10) -0.0010(8) -0.0022(8) -0.0063(8) C3 0.0231(10) 0.0188(9) 0.0266(11) -0.0051(8) 0.0048(8) -0.0114(8) C4 0.0313(11) 0.0159(9) 0.0167(9) -0.0050(7) 0.0053(8) -0.0126(8) C5 0.0280(11) 0.0177(9) 0.0214(10) 0.0022(8) -0.0010(8) -0.0042(8) C6 0.0193(10) 0.0192(9) 0.0214(10) -0.0018(8) 0.0024(8) -0.0054(8) C7 0.0418(14) 0.0252(11) 0.0220(11) 0.0004(9) 0.0057(9) -0.0175(10) C8 0.0161(9) 0.0143(8) 0.0164(9) -0.0037(7) 0.0011(7) -0.0049(7) C9 0.0152(9) 0.0145(8) 0.0143(8) -0.0013(7) 0.0009(7) -0.0060(7) C10 0.0205(10) 0.0169(9) 0.0159(9) -0.0016(7) 0.0005(7) -0.0079(8) C11 0.0170(9) 0.0138(8) 0.0152(9) -0.0024(7) 0.0026(7) -0.0057(7) C12 0.0222(10) 0.0239(10) 0.0133(9) -0.0011(7) -0.0008(7) -0.0095(8) C13 0.0279(11) 0.0233(10) 0.0137(9) 0.0011(8) 0.0018(8) -0.0110(8) C14 0.0247(11) 0.0235(10) 0.0193(10) -0.0013(8) 0.0054(8) -0.0149(9) C15 0.0211(10) 0.0285(11) 0.0210(10) 0.0005(8) -0.0023(8) -0.0134(9) C16 0.0197(10) 0.0215(9) 0.0171(9) 0.0030(8) -0.0006(7) -0.0085(8) C17 0.0127(9) 0.0152(8) 0.0167(9) -0.0037(7) 0.0016(7) -0.0030(7) C18 0.0144(9) 0.0118(8) 0.0210(9) -0.0045(7) 0.0026(7) -0.0021(7) C19 0.0228(10) 0.0169(9) 0.0188(9) -0.0041(8) -0.0009(8) -0.0073(8) C20 0.0242(10) 0.0145(9) 0.0218(10) -0.0048(8) 0.0004(8) -0.0085(8) C21 0.0152(9) 0.0129(8) 0.0206(9) -0.0025(7) 0.0003(7) -0.0010(7) C22 0.0181(9) 0.0184(9) 0.0239(10) -0.0020(8) -0.0039(8) -0.0065(8) C23 0.0171(9) 0.0166(9) 0.0258(10) -0.0016(8) -0.0028(8) -0.0067(8) C24 0.0193(10) 0.0146(9) 0.0200(9) -0.0031(7) 0.0014(7) -0.0031(7) C25 0.0244(11) 0.0227(10) 0.0195(10) 0.0038(8) -0.0012(8) -0.0115(8) 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' Cl Cl 0.1484 0.1585 '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_ _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 117.69(9) . . ? O1 S N1 112.38(8) . . ? O1 S C1 107.54(9) . . ? O2 S N1 105.52(9) . . ? O2 S C1 110.22(9) . . ? N1 S C1 102.46(9) . . ? C17 O3 C10 104.46(14) . . ? S N1 H1 112.6(17) . . ? C8 N1 S 118.67(13) . . ? C8 N1 H1 113.1(17) . . ? C17 N2 C9 105.97(15) . . ? C2 C1 S 119.65(15) . . ? C6 C1 S 119.15(15) . . ? C6 C1 C2 121.19(18) . . ? C1 C2 H2 120.5 . . ? C3 C2 C1 118.97(19) . . ? C3 C2 H2 120.5 . . ? C2 C3 H3 119.4 . . ? C2 C3 C4 121.27(19) . . ? C4 C3 H3 119.4 . . ? C3 C4 C7 120.3(2) . . ? C5 C4 C3 118.55(18) . . ? C5 C4 C7 121.1(2) . . ? C4 C5 H5 119.4 . . ? C4 C5 C6 121.2(2) . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.77(19) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? 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 110.1 . . ? N1 C8 H8B 110.1 . . ? N1 C8 C9 108.23(15) . . ? H8A C8 H8B 108.4 . . ? C9 C8 H8A 110.1 . . ? C9 C8 H8B 110.1 . . ? N2 C9 C8 106.25(15) . . ? N2 C9 C10 102.54(14) . . ? N2 C9 C11 113.68(15) . . ? C10 C9 C8 109.65(15) . . ? C11 C9 C8 110.30(15) . . ? C11 C9 C10 113.91(16) . . ? O3 C10 C9 103.04(14) . . ? O3 C10 H10A 111.2 . . ? O3 C10 H10B 111.2 . . ? C9 C10 H10A 111.2 . . ? C9 C10 H10B 111.2 . . ? H10A C10 H10B 109.1 . . ? C12 C11 C9 118.40(17) . . ? C16 C11 C9 122.53(17) . . ? C16 C11 C12 118.98(18) . . ? C11 C12 H12 119.2 . . ? C13 C12 C11 121.70(19) . . ? C13 C12 H12 119.2 . . ? C12 C13 H13 120.9 . . ? C12 C13 C14 118.13(19) . . ? C14 C13 H13 120.9 . . ? C13 C14 Cl 118.50(16) . . ? C15 C14 Cl 119.79(16) . . ? C15 C14 C13 121.70(19) . . ? C14 C15 H15 120.4 . . ? C14 C15 C16 119.26(19) . . ? C16 C15 H15 120.4 . . ? C11 C16 C15 120.22(18) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? O3 C17 C18 116.41(16) . . ? N2 C17 O3 118.07(17) . . ? N2 C17 C18 125.45(17) . . ? C19 C18 C17 121.63(18) . . ? C19 C18 C23 119.75(18) . . ? C23 C18 C17 118.57(17) . . ? C18 C19 H19 119.9 . . ? C20 C19 C18 120.17(18) . . ? C20 C19 H19 119.9 . . ? C19 C20 H20 120.0 . . ? C19 C20 C21 120.05(18) . . ? C21 C20 H20 120.0 . . ? C20 C21 C24 122.70(17) . . ? C22 C21 C20 119.53(18) . . ? C22 C21 C24 117.72(18) . . ? C21 C22 H22 119.7 . . ? C23 C22 C21 120.52(19) . . ? C23 C22 H22 119.7 . . ? C18 C23 H23 120.0 . . ? C22 C23 C18 119.91(18) . . ? C22 C23 H23 120.0 . . ? O4 C24 C21 121.12(18) . . ? O4 C24 C25 122.28(18) . . ? C21 C24 C25 116.57(17) . . ? Br C25 H25A 109.2 . . ? Br C25 H25B 109.2 . . ? C24 C25 Br 112.05(14) . . ? C24 C25 H25A 109.2 . . ? C24 C25 H25B 109.2 . . ? H25A C25 H25B 107.9 . . ? 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 C25 1.922(2) . ? Cl C14 1.743(2) . ? S O1 1.4389(15) . ? S O2 1.4412(14) . ? S N1 1.6170(17) . ? S C1 1.7623(19) . ? O3 C10 1.453(2) . ? O3 C17 1.370(2) . ? O4 C24 1.213(2) . ? N1 H1 0.805(16) . ? N1 C8 1.467(2) . ? N2 C9 1.483(2) . ? N2 C17 1.273(2) . ? C1 C2 1.388(3) . ? C1 C6 1.385(3) . ? C2 H2 0.9500 . ? C2 C3 1.386(3) . ? C3 H3 0.9500 . ? C3 C4 1.390(3) . ? C4 C5 1.389(3) . ? C4 C7 1.506(3) . ? C5 H5 0.9500 . ? C5 C6 1.394(3) . ? 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 1.540(3) . ? C9 C10 1.538(3) . ? C9 C11 1.513(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.388(3) . ? C11 C16 1.388(3) . ? C12 H12 0.9500 . ? C12 C13 1.384(3) . ? C13 H13 0.9500 . ? C13 C14 1.388(3) . ? C14 C15 1.375(3) . ? C15 H15 0.9500 . ? C15 C16 1.397(3) . ? C16 H16 0.9500 . ? C17 C18 1.463(3) . ? C18 C19 1.392(3) . ? C18 C23 1.399(3) . ? C19 H19 0.9500 . ? C19 C20 1.386(3) . ? C20 H20 0.9500 . ? C20 C21 1.395(3) . ? C21 C22 1.395(3) . ? C21 C24 1.491(3) . ? C22 H22 0.9500 . ? C22 C23 1.378(3) . ? C23 H23 0.9500 . ? C24 C25 1.514(3) . ? C25 H25A 0.9900 . ? C25 H25B 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 O1 0.805(16) 2.41(2) 3.102(2) 145(2) 2_766 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cl C14 C15 C16 179.57(17) . . . . ? S N1 C8 C9 -158.47(13) . . . . ? S C1 C2 C3 179.20(15) . . . . ? S C1 C6 C5 -177.90(15) . . . . ? O1 S N1 C8 -39.80(17) . . . . ? O1 S C1 C2 166.67(15) . . . . ? O1 S C1 C6 -14.62(18) . . . . ? O2 S N1 C8 -169.28(14) . . . . ? O2 S C1 C2 -63.86(17) . . . . ? O2 S C1 C6 114.85(16) . . . . ? O3 C17 C18 C19 8.4(3) . . . . ? O3 C17 C18 C23 -174.27(17) . . . . ? O4 C24 C25 Br -8.7(3) . . . . ? N1 S C1 C2 48.06(17) . . . . ? N1 S C1 C6 -133.23(16) . . . . ? N1 C8 C9 N2 -55.27(18) . . . . ? N1 C8 C9 C10 -165.40(15) . . . . ? N1 C8 C9 C11 68.36(19) . . . . ? N2 C9 C10 O3 -23.89(18) . . . . ? N2 C9 C11 C12 -174.23(17) . . . . ? N2 C9 C11 C16 9.4(3) . . . . ? N2 C17 C18 C19 -168.43(19) . . . . ? N2 C17 C18 C23 8.9(3) . . . . ? C1 S N1 C8 75.33(15) . . . . ? C1 C2 C3 C4 -1.4(3) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? C2 C3 C4 C5 0.8(3) . . . . ? C2 C3 C4 C7 179.46(19) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C1 -1.3(3) . . . . ? C6 C1 C2 C3 0.5(3) . . . . ? C7 C4 C5 C6 -178.09(19) . . . . ? C8 C9 C10 O3 88.68(17) . . . . ? C8 C9 C11 C12 66.6(2) . . . . ? C8 C9 C11 C16 -109.8(2) . . . . ? C9 N2 C17 O3 -7.5(2) . . . . ? C9 N2 C17 C18 169.30(18) . . . . ? C9 C11 C12 C13 -176.22(19) . . . . ? C9 C11 C16 C15 176.62(19) . . . . ? C10 O3 C17 N2 -8.8(2) . . . . ? C10 O3 C17 C18 174.09(16) . . . . ? C10 C9 C11 C12 -57.2(2) . . . . ? C10 C9 C11 C16 126.4(2) . . . . ? C11 C9 C10 O3 -147.17(16) . . . . ? C11 C12 C13 C14 -0.9(3) . . . . ? C12 C11 C16 C15 0.3(3) . . . . ? C12 C13 C14 Cl -179.04(16) . . . . ? C12 C13 C14 C15 1.0(3) . . . . ? C13 C14 C15 C16 -0.4(3) . . . . ? C14 C15 C16 C11 -0.2(3) . . . . ? C16 C11 C12 C13 0.3(3) . . . . ? C17 O3 C10 C9 20.05(18) . . . . ? C17 N2 C9 C8 -95.68(17) . . . . ? C17 N2 C9 C10 19.39(19) . . . . ? C17 N2 C9 C11 142.83(17) . . . . ? C17 C18 C19 C20 175.23(18) . . . . ? C17 C18 C23 C22 -176.81(18) . . . . ? C18 C19 C20 C21 1.2(3) . . . . ? C19 C18 C23 C22 0.6(3) . . . . ? C19 C20 C21 C22 1.2(3) . . . . ? C19 C20 C21 C24 -176.07(18) . . . . ? C20 C21 C22 C23 -2.7(3) . . . . ? C20 C21 C24 O4 -166.0(2) . . . . ? C20 C21 C24 C25 15.7(3) . . . . ? C21 C22 C23 C18 1.8(3) . . . . ? C21 C24 C25 Br 169.63(14) . . . . ? C22 C21 C24 O4 16.7(3) . . . . ? C22 C21 C24 C25 -161.61(19) . . . . ? C23 C18 C19 C20 -2.1(3) . . . . ? C24 C21 C22 C23 174.70(18) . . . . ?