#------------------------------------------------------------------------------ #$Date: 2020-05-13 02:17:54 +0300 (Wed, 13 May 2020) $ #$Revision: 251993 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/83/4038348.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_4038348 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 H27 Cl N2 O3 S' _chemical_formula_sum 'C23 H27 Cl N2 O3 S' _chemical_formula_weight 446.97 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2019-01-17 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 98.815(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.9218(6) _cell_length_b 21.635(2) _cell_length_c 17.5661(16) _cell_measurement_reflns_used 8733 _cell_measurement_temperature 230(2) _cell_measurement_theta_max 21.64 _cell_measurement_theta_min 2.22 _cell_volume 2224.0(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 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL 2018/3 multi-CPU version (Sheldrick, 2015a)' _computing_structure_solution 'ShelXT 2018/2 (Sheldrick, 2015)' _diffrn_ambient_temperature 230(2) _diffrn_detector_area_resol_mean 10.4 _diffrn_detector_type 'Bruker PHOTON 100 CMOS' _diffrn_measured_fraction_theta_full 0.999 _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 0.0451 _diffrn_reflns_av_unetI/netI 0.0282 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 35052 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.026 _diffrn_reflns_theta_max 25.026 _diffrn_reflns_theta_min 2.218 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\mS microsource' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.293 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.9578 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1305 before and 0.0472 after correction. The Ratio of minimum to maximum transmission is 0.9578. The \l/2 correction factor is Not present. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.335 _exptl_crystal_description prism _exptl_crystal_F_000 944 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.155 _exptl_crystal_size_min 0.132 _refine_diff_density_max 0.170 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.034 _refine_ls_extinction_coef 0.0093(8) _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 constr _refine_ls_matrix_type full _refine_ls_number_parameters 273 _refine_ls_number_reflns 3912 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0656 _refine_ls_R_factor_gt 0.0397 _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^)+(0.0423P)^2^+0.7924P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0915 _refine_ls_wR_factor_ref 0.1014 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2822 _reflns_number_total 3912 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jo0c00656_si_003.cif _cod_data_source_block 19srv004 _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_original_cell_volume 2223.9(4) _cod_database_code 4038348 _ccdc_polymorph 'room temperature phase' _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H,H) groups 2. Others Sof(H7D)=Sof(H7E)=Sof(H7F)=1-FVAR(1) Sof(H7C)=Sof(H7A)=Sof(H7B)=FVAR(1) 3.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B) 3.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C5(H5), C6(H6), C19(H19), C20(H20), C22(H22), C23(H23) 3.c Disordered Me refined with riding coordinates: C7(H7C,H7A,H7B,H7D,H7E,H7F) ; _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 0.899 _shelx_estimated_absorpt_t_max 0.962 _shelx_res_checksum 3249 _shelx_res_file ; TITL 19srv002_a.res in P2(1)/c 19srv003.res created by SHELXL-2018/3 at 13:32:37 on 14-Jan-2019 REM Old TITL 19srv002 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.212, Rweak 0.019, Alpha 0.041 REM 0.643 for 124 systematic absences, Orientation as input REM Formula found by SHELXT: C23 N3 O2 Cl2 CELL 0.71073 5.9218 21.6348 17.5661 90 98.815 90 ZERR 4 0.0006 0.002 0.0016 0 0.004 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N O S UNIT 92 108 4 8 12 4 L.S. 4 PLAN 7 SIZE 0.132 0.155 0.37 TEMP 0 BOND list 4 fmap 2 53 acta REM REM REM WGHT 0.042300 0.792400 EXTI 0.009329 FVAR 0.58364 0.63909 CL 3 0.015075 0.454701 0.098797 11.00000 0.11690 0.06750 = 0.07169 0.02344 -0.00029 0.01195 S 6 0.637346 0.326303 0.552250 11.00000 0.04639 0.05081 = 0.05050 0.00420 -0.01113 -0.00722 O1 5 0.777329 0.362141 0.509448 11.00000 0.04582 0.06503 = 0.07189 0.00148 0.00108 -0.01783 O2 5 0.740761 0.289065 0.614882 11.00000 0.07094 0.06848 = 0.06685 0.01197 -0.02913 -0.00173 O3 5 0.816198 0.223222 0.360728 11.00000 0.03887 0.12533 = 0.09175 0.00719 0.00797 0.03374 N1 4 0.482713 0.280153 0.490632 11.00000 0.03795 0.04280 = 0.04413 0.00372 -0.00225 -0.00292 N2 4 0.432827 0.219891 0.331593 11.00000 0.04414 0.05915 = 0.04744 -0.00241 0.00277 0.01724 C1 1 0.445125 0.377502 0.587144 11.00000 0.05725 0.04860 = 0.03997 -0.00234 -0.00499 -0.01368 C2 1 0.396698 0.433774 0.551539 11.00000 0.06217 0.05101 = 0.05790 0.00076 0.00878 -0.00731 AFIX 43 H2 2 0.469049 0.445284 0.510321 11.00000 -1.20000 AFIX 0 C3 1 0.241195 0.472846 0.577097 11.00000 0.06882 0.05833 = 0.07718 -0.00633 0.00025 -0.00444 AFIX 43 H3 2 0.209932 0.510772 0.552842 11.00000 -1.20000 AFIX 0 C4 1 0.130471 0.457008 0.637972 11.00000 0.06282 0.08258 = 0.06583 -0.03266 0.00450 -0.01518 C5 1 0.179414 0.400386 0.671873 11.00000 0.09466 0.09722 = 0.04781 -0.02052 0.01864 -0.02886 AFIX 43 H5 2 0.104623 0.388641 0.712427 11.00000 -1.20000 AFIX 0 C6 1 0.334857 0.360495 0.648020 11.00000 0.09415 0.06725 = 0.04020 -0.00182 0.00570 -0.01680 AFIX 43 H6 2 0.365668 0.322596 0.672389 11.00000 -1.20000 AFIX 0 C7 1 -0.039322 0.499853 0.665515 11.00000 0.08023 0.12760 = 0.11615 -0.05667 0.01831 -0.00322 AFIX 123 H7C 2 -0.051190 0.536961 0.635200 21.00000 -1.20000 H7A 2 -0.185850 0.479993 0.660323 21.00000 -1.20000 H7B 2 0.010488 0.510003 0.718635 21.00000 -1.20000 H7D 2 -0.099845 0.481010 0.707572 -21.00000 -1.20000 H7E 2 0.034815 0.537979 0.682449 -21.00000 -1.20000 H7F 2 -0.161523 0.507968 0.624137 -21.00000 -1.20000 AFIX 0 C8 1 0.386948 0.308364 0.416098 11.00000 0.02959 0.04875 = 0.04350 0.00372 0.00070 0.00137 AFIX 23 H8A 2 0.408826 0.352736 0.420337 11.00000 -1.20000 H8B 2 0.223591 0.300772 0.407102 11.00000 -1.20000 AFIX 0 C9 1 0.487349 0.285734 0.344855 11.00000 0.02728 0.06162 = 0.04828 0.00096 0.00575 0.00130 C10 1 0.751079 0.286756 0.354951 11.00000 0.03122 0.11296 = 0.06789 -0.00040 0.00892 0.00612 AFIX 23 H10A 2 0.803436 0.306068 0.310972 11.00000 -1.20000 H10B 2 0.814090 0.309113 0.401222 11.00000 -1.20000 AFIX 0 C11 1 0.619097 0.190601 0.343490 11.00000 0.05350 0.09065 = 0.05766 -0.00194 0.00485 0.03422 C12 1 0.642302 0.121432 0.340326 11.00000 0.10609 0.10037 = 0.08033 -0.01067 0.00176 0.06835 AFIX 23 H12A 2 0.784457 0.109347 0.371858 11.00000 -1.20000 H12B 2 0.650773 0.109278 0.287687 11.00000 -1.20000 AFIX 0 C13 1 0.446718 0.086877 0.367824 11.00000 0.11952 0.05812 = 0.08837 -0.01833 -0.01036 0.03214 AFIX 23 H13A 2 0.305799 0.109172 0.350980 11.00000 -1.20000 H13B 2 0.432860 0.046506 0.343535 11.00000 -1.20000 AFIX 0 C14 1 0.473903 0.078368 0.454327 11.00000 0.10779 0.04917 = 0.09285 0.00236 -0.01797 0.02147 AFIX 23 H14A 2 0.608666 0.053362 0.470522 11.00000 -1.20000 H14B 2 0.342983 0.055598 0.466554 11.00000 -1.20000 AFIX 0 C15 1 0.495729 0.138109 0.500633 11.00000 0.07595 0.05204 = 0.06178 0.00869 -0.01680 0.00626 AFIX 23 H15A 2 0.530103 0.127974 0.554967 11.00000 -1.20000 H15B 2 0.623428 0.161644 0.487249 11.00000 -1.20000 AFIX 0 C16 1 0.283578 0.178255 0.487650 11.00000 0.05400 0.04756 = 0.05126 0.00588 -0.00341 -0.01001 AFIX 23 H16A 2 0.237152 0.184042 0.432723 11.00000 -1.20000 H16B 2 0.160597 0.157062 0.507554 11.00000 -1.20000 AFIX 0 C17 1 0.319468 0.240575 0.525746 11.00000 0.04862 0.05161 = 0.04930 0.00419 0.00457 -0.00801 AFIX 23 H17A 2 0.173622 0.261679 0.521823 11.00000 -1.20000 H17B 2 0.377180 0.234828 0.580006 11.00000 -1.20000 AFIX 0 C18 1 0.375433 0.325653 0.278506 11.00000 0.03336 0.05835 = 0.04229 0.00021 0.01185 -0.00087 C19 1 0.181973 0.306705 0.230071 11.00000 0.04152 0.04895 = 0.03945 0.00034 0.01046 0.00060 AFIX 43 H19 2 0.125360 0.267073 0.235191 11.00000 -1.20000 AFIX 0 C20 1 0.070908 0.345676 0.174049 11.00000 0.05057 0.05487 = 0.04172 -0.00106 0.00384 0.00104 AFIX 43 H20 2 -0.059894 0.332575 0.141918 11.00000 -1.20000 AFIX 0 C21 1 0.156192 0.403777 0.166567 11.00000 0.07034 0.05512 = 0.04327 0.00703 0.01134 0.00388 C22 1 0.351025 0.423420 0.212636 11.00000 0.07827 0.06065 = 0.06943 0.01332 0.01509 -0.02043 AFIX 43 H22 2 0.410220 0.462515 0.205917 11.00000 -1.20000 AFIX 0 C23 1 0.457427 0.384697 0.268720 11.00000 0.05495 0.07583 = 0.06325 0.00771 0.00239 -0.02198 AFIX 43 H23 2 0.587361 0.398317 0.300888 11.00000 -1.20000 AFIX 0 HKLF 4 REM 19srv002_a.res in P2(1)/c REM wR2 = 0.1014, GooF = S = 1.027, Restrained GooF = 1.027 for all data REM R1 = 0.0397 for 2822 Fo > 4sig(Fo) and 0.0656 for all 3912 data REM 273 parameters refined using 0 restraints END WGHT 0.0420 0.7987 REM Highest difference peak 0.170, deepest hole -0.227, 1-sigma level 0.034 Q1 1 0.5237 0.3581 0.5663 11.00000 0.05 0.17 Q2 1 0.4491 0.2968 0.4581 11.00000 0.05 0.15 Q3 1 0.3578 0.3602 0.6025 11.00000 0.05 0.15 Q4 1 0.4149 0.2617 0.5034 11.00000 0.05 0.15 Q5 1 0.5010 0.2053 0.3633 11.00000 0.05 0.14 Q6 1 0.4715 0.3413 0.2567 11.00000 0.05 0.14 Q7 1 0.7547 0.1378 0.3095 11.00000 0.05 0.14 ; _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+1/2, -z+1/2' '-x, -y, -z' 'x, -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 Cl Cl 0.01508(14) 0.45470(3) 0.09880(4) 0.0869(3) Uani 1 1 d . . . . . S S 0.63735(9) 0.32630(3) 0.55225(3) 0.05117(18) Uani 1 1 d . . . . . O1 O 0.7773(2) 0.36214(7) 0.50945(9) 0.0617(4) Uani 1 1 d . . . . . O2 O 0.7408(3) 0.28907(7) 0.61488(9) 0.0729(5) Uani 1 1 d . . . . . O3 O 0.8162(3) 0.22322(10) 0.36073(11) 0.0855(6) Uani 1 1 d . . . . . N1 N 0.4827(3) 0.28015(7) 0.49063(9) 0.0425(4) Uani 1 1 d . . . . . N2 N 0.4328(3) 0.21989(8) 0.33159(10) 0.0507(5) Uani 1 1 d . . . . . C1 C 0.4451(4) 0.37750(10) 0.58714(11) 0.0499(5) Uani 1 1 d . . . . . C2 C 0.3967(4) 0.43377(10) 0.55154(13) 0.0571(6) Uani 1 1 d . . . . . H2 H 0.469049 0.445284 0.510321 0.068 Uiso 1 1 calc R . . . . C3 C 0.2412(4) 0.47285(12) 0.57710(16) 0.0693(7) Uani 1 1 d . . . . . H3 H 0.209932 0.510772 0.552842 0.083 Uiso 1 1 calc R . . . . C4 C 0.1305(4) 0.45701(14) 0.63797(16) 0.0710(7) Uani 1 1 d . . . . . C5 C 0.1794(5) 0.40039(15) 0.67187(14) 0.0791(8) Uani 1 1 d . . . . . H5 H 0.104623 0.388641 0.712427 0.095 Uiso 1 1 calc R . . . . C6 C 0.3349(5) 0.36049(12) 0.64802(13) 0.0677(7) Uani 1 1 d . . . . . H6 H 0.365668 0.322596 0.672389 0.081 Uiso 1 1 calc R . . . . C7 C -0.0393(5) 0.49985(16) 0.6655(2) 0.1077(12) Uani 1 1 d . . . . . H7C H -0.051190 0.536961 0.635200 0.129 Uiso 0.64(3) 1 calc R . P . . H7A H -0.185850 0.479993 0.660323 0.129 Uiso 0.64(3) 1 calc R . P . . H7B H 0.010488 0.510003 0.718635 0.129 Uiso 0.64(3) 1 calc R . P . . H7D H -0.099845 0.481010 0.707572 0.129 Uiso 0.36(3) 1 calc R . P . . H7E H 0.034815 0.537979 0.682449 0.129 Uiso 0.36(3) 1 calc R . P . . H7F H -0.161523 0.507968 0.624137 0.129 Uiso 0.36(3) 1 calc R . P . . C8 C 0.3869(3) 0.30836(9) 0.41610(10) 0.0411(5) Uani 1 1 d . . . . . H8A H 0.408826 0.352736 0.420337 0.049 Uiso 1 1 calc R . . . . H8B H 0.223591 0.300772 0.407102 0.049 Uiso 1 1 calc R . . . . C9 C 0.4873(3) 0.28573(10) 0.34485(11) 0.0457(5) Uani 1 1 d . . . . . C10 C 0.7511(4) 0.28676(14) 0.35495(15) 0.0706(7) Uani 1 1 d . . . . . H10A H 0.803436 0.306068 0.310972 0.085 Uiso 1 1 calc R . . . . H10B H 0.814090 0.309113 0.401222 0.085 Uiso 1 1 calc R . . . . C11 C 0.6191(4) 0.19060(13) 0.34349(14) 0.0677(7) Uani 1 1 d . . . . . C12 C 0.6423(6) 0.12143(15) 0.34033(18) 0.0969(11) Uani 1 1 d . . . . . H12A H 0.784457 0.109347 0.371858 0.116 Uiso 1 1 calc R . . . . H12B H 0.650773 0.109278 0.287687 0.116 Uiso 1 1 calc R . . . . C13 C 0.4467(6) 0.08688(13) 0.36782(17) 0.0914(10) Uani 1 1 d . . . . . H13A H 0.305799 0.109172 0.350980 0.110 Uiso 1 1 calc R . . . . H13B H 0.432860 0.046506 0.343535 0.110 Uiso 1 1 calc R . . . . C14 C 0.4739(6) 0.07837(11) 0.45433(17) 0.0868(9) Uani 1 1 d . . . . . H14A H 0.608666 0.053362 0.470522 0.104 Uiso 1 1 calc R . . . . H14B H 0.342983 0.055598 0.466554 0.104 Uiso 1 1 calc R . . . . C15 C 0.4957(4) 0.13811(10) 0.50063(14) 0.0661(7) Uani 1 1 d . . . . . H15A H 0.530103 0.127974 0.554967 0.079 Uiso 1 1 calc R . . . . H15B H 0.623428 0.161644 0.487249 0.079 Uiso 1 1 calc R . . . . C16 C 0.2836(4) 0.17826(9) 0.48765(12) 0.0521(6) Uani 1 1 d . . . . . H16A H 0.237152 0.184042 0.432723 0.063 Uiso 1 1 calc R . . . . H16B H 0.160597 0.157062 0.507554 0.063 Uiso 1 1 calc R . . . . C17 C 0.3195(4) 0.24058(9) 0.52575(12) 0.0501(5) Uani 1 1 d . . . . . H17A H 0.173622 0.261679 0.521823 0.060 Uiso 1 1 calc R . . . . H17B H 0.377180 0.234828 0.580006 0.060 Uiso 1 1 calc R . . . . C18 C 0.3754(3) 0.32565(10) 0.27851(11) 0.0440(5) Uani 1 1 d . . . . . C19 C 0.1820(3) 0.30670(10) 0.23007(11) 0.0429(5) Uani 1 1 d . . . . . H19 H 0.125360 0.267073 0.235191 0.051 Uiso 1 1 calc R . . . . C20 C 0.0709(4) 0.34568(10) 0.17405(11) 0.0494(5) Uani 1 1 d . . . . . H20 H -0.059894 0.332575 0.141918 0.059 Uiso 1 1 calc R . . . . C21 C 0.1562(4) 0.40378(11) 0.16657(12) 0.0560(6) Uani 1 1 d . . . . . C22 C 0.3510(5) 0.42342(12) 0.21264(14) 0.0691(7) Uani 1 1 d . . . . . H22 H 0.410220 0.462515 0.205917 0.083 Uiso 1 1 calc R . . . . C23 C 0.4574(4) 0.38470(12) 0.26872(14) 0.0654(7) Uani 1 1 d . . . . . H23 H 0.587361 0.398317 0.300888 0.078 Uiso 1 1 calc R . . . . 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 Cl 0.1169(6) 0.0675(4) 0.0717(4) 0.0234(3) -0.0003(4) 0.0119(4) S 0.0464(3) 0.0508(3) 0.0505(3) 0.0042(3) -0.0111(2) -0.0072(3) O1 0.0458(9) 0.0650(10) 0.0719(10) 0.0015(8) 0.0011(7) -0.0178(8) O2 0.0709(11) 0.0685(11) 0.0668(10) 0.0120(8) -0.0291(9) -0.0017(9) O3 0.0389(10) 0.1253(17) 0.0917(13) 0.0072(12) 0.0080(9) 0.0337(11) N1 0.0379(9) 0.0428(9) 0.0441(9) 0.0037(7) -0.0022(7) -0.0029(7) N2 0.0441(10) 0.0591(11) 0.0474(10) -0.0024(8) 0.0028(8) 0.0172(9) C1 0.0572(14) 0.0486(12) 0.0400(11) -0.0023(10) -0.0050(10) -0.0137(10) C2 0.0622(15) 0.0510(13) 0.0579(14) 0.0008(11) 0.0088(11) -0.0073(11) C3 0.0688(17) 0.0583(15) 0.0772(18) -0.0063(13) 0.0002(14) -0.0044(13) C4 0.0628(16) 0.083(2) 0.0658(17) -0.0327(15) 0.0045(13) -0.0152(14) C5 0.095(2) 0.097(2) 0.0478(15) -0.0205(15) 0.0186(14) -0.0289(18) C6 0.094(2) 0.0672(16) 0.0402(13) -0.0018(12) 0.0057(13) -0.0168(15) C7 0.080(2) 0.128(3) 0.116(3) -0.057(2) 0.0183(19) -0.003(2) C8 0.0296(10) 0.0488(11) 0.0435(11) 0.0037(9) 0.0007(8) 0.0014(9) C9 0.0273(10) 0.0616(14) 0.0483(12) 0.0010(10) 0.0058(8) 0.0013(9) C10 0.0312(12) 0.113(2) 0.0679(16) -0.0004(15) 0.0089(11) 0.0061(14) C11 0.0535(16) 0.0906(19) 0.0577(15) -0.0019(13) 0.0048(11) 0.0342(15) C12 0.106(3) 0.100(2) 0.080(2) -0.0107(17) 0.0018(18) 0.068(2) C13 0.120(3) 0.0581(17) 0.088(2) -0.0183(15) -0.0104(19) 0.0321(18) C14 0.108(2) 0.0492(15) 0.093(2) 0.0024(14) -0.0180(17) 0.0215(15) C15 0.0759(17) 0.0520(14) 0.0618(14) 0.0087(11) -0.0168(12) 0.0063(12) C16 0.0540(13) 0.0476(12) 0.0513(13) 0.0059(10) -0.0034(10) -0.0100(10) C17 0.0486(12) 0.0516(13) 0.0493(12) 0.0042(10) 0.0046(10) -0.0080(10) C18 0.0334(11) 0.0583(13) 0.0423(11) 0.0002(10) 0.0118(9) -0.0009(10) C19 0.0415(11) 0.0490(12) 0.0395(11) 0.0003(9) 0.0105(9) 0.0006(9) C20 0.0506(13) 0.0549(13) 0.0417(11) -0.0011(10) 0.0038(9) 0.0010(11) C21 0.0703(16) 0.0551(14) 0.0433(12) 0.0070(10) 0.0113(11) 0.0039(12) C22 0.0783(18) 0.0606(15) 0.0694(16) 0.0133(13) 0.0151(14) -0.0204(14) C23 0.0549(15) 0.0758(17) 0.0632(15) 0.0077(13) 0.0024(12) -0.0220(13) 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' 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 0.00 0.0510 0.00 -1.00 0.00 0.0590 0.00 1.00 -1.00 0.0660 0.00 -1.00 1.00 0.0650 0.00 -1.00 -1.00 0.0760 0.00 1.00 1.00 0.0760 -2.00 2.00 1.00 0.1620 1.00 0.00 -1.00 0.1620 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 107.00(9) . . ? O1 S C1 107.41(10) . . ? O2 S O1 119.85(10) . . ? O2 S N1 107.17(9) . . ? O2 S C1 108.10(11) . . ? N1 S C1 106.63(9) . . ? C11 O3 C10 105.73(17) . . ? C8 N1 S 115.60(13) . . ? C8 N1 C17 114.72(15) . . ? C17 N1 S 114.00(13) . . ? C11 N2 C9 107.2(2) . . ? C2 C1 S 119.82(18) . . ? C2 C1 C6 119.7(2) . . ? C6 C1 S 120.46(18) . . ? C3 C2 C1 119.9(2) . . ? C2 C3 C4 121.4(3) . . ? C3 C4 C7 121.2(3) . . ? C5 C4 C3 117.6(3) . . ? C5 C4 C7 121.2(3) . . ? C6 C5 C4 122.3(3) . . ? C5 C6 C1 119.1(2) . . ? N1 C8 C9 116.36(16) . . ? N2 C9 C8 109.43(16) . . ? N2 C9 C10 103.03(18) . . ? N2 C9 C18 111.70(16) . . ? C10 C9 C8 114.22(17) . . ? C18 C9 C8 105.34(16) . . ? C18 C9 C10 113.24(18) . . ? O3 C10 C9 104.6(2) . . ? O3 C11 C12 116.4(2) . . ? N2 C11 O3 118.4(2) . . ? N2 C11 C12 125.2(3) . . ? C11 C12 C13 113.6(2) . . ? C14 C13 C12 114.2(3) . . ? C13 C14 C15 114.8(2) . . ? C16 C15 C14 113.9(2) . . ? C17 C16 C15 112.89(18) . . ? N1 C17 C16 112.71(18) . . ? C19 C18 C9 121.83(18) . . ? C19 C18 C23 118.06(19) . . ? C23 C18 C9 119.94(18) . . ? C18 C19 C20 121.11(19) . . ? C21 C20 C19 119.1(2) . . ? C20 C21 Cl 120.13(18) . . ? C20 C21 C22 121.2(2) . . ? C22 C21 Cl 118.70(18) . . ? C23 C22 C21 119.2(2) . . ? C22 C23 C18 121.4(2) . . ? 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 Cl C21 1.739(2) . ? S O1 1.4299(16) . ? S O2 1.4241(15) . ? S N1 1.6441(16) . ? S C1 1.764(2) . ? O3 C10 1.427(3) . ? O3 C11 1.358(3) . ? N1 C8 1.477(2) . ? N1 C17 1.494(3) . ? N2 C9 1.471(3) . ? N2 C11 1.261(3) . ? C1 C2 1.379(3) . ? C1 C6 1.385(3) . ? C2 C3 1.375(3) . ? C3 C4 1.380(4) . ? C4 C5 1.373(4) . ? C4 C7 1.501(4) . ? C5 C6 1.373(4) . ? C8 C9 1.545(3) . ? C9 C10 1.545(3) . ? C9 C18 1.519(3) . ? C11 C12 1.505(4) . ? C12 C13 1.518(4) . ? C13 C14 1.515(4) . ? C14 C15 1.522(3) . ? C15 C16 1.516(3) . ? C16 C17 1.506(3) . ? C18 C19 1.380(3) . ? C18 C23 1.387(3) . ? C19 C20 1.383(3) . ? C20 C21 1.368(3) . ? C21 C22 1.371(3) . ? C22 C23 1.371(3) . ?