#------------------------------------------------------------------------------ #$Date: 2024-11-01 03:34:50 +0200 (Fri, 01 Nov 2024) $ #$Revision: 295709 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160197.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_7160197 loop_ _publ_author_name 'Banerjee, Ankush' 'Brisco, Tiffany A.' 'Ray, Sneha' 'Datta, Arani' 'Zhang, Xiaoyu' 'Zhang, Zhen' 'Busse, Alexander A.' 'Niederstrasser, Hanspeter' 'Sumida, Krissty' 'Posner, Bruce A.' 'Wetzel, Dawn M.' 'Phillips, Margaret A.' 'Smith, Myles W.' _publ_section_title ; Synthesis of the 5/5-Spiroindimicin Alkaloids: Development of a General Synthetic Approach and Biological Investigations ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01552E _journal_year 2024 _chemical_formula_moiety 'C23 H18 Cl N3 O2' _chemical_formula_sum 'C23 H18 Cl N3 O2' _chemical_formula_weight 403.85 _chemical_name_systematic 'spiroindimicin F' _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_block_doi 10.5517/ccdc.csd.cc2fpr74 _audit_creation_date 2023-04-07 _audit_creation_method ; Olex2 1.5 (compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380) ; _audit_update_record ; 2023-08-17 deposited with the CCDC. 2024-10-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.8740(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.26480(10) _cell_length_b 14.87010(10) _cell_length_c 12.73740(10) _cell_measurement_reflns_used 22973 _cell_measurement_temperature 100.01(12) _cell_measurement_theta_max 76.8160 _cell_measurement_theta_min 2.9590 _cell_volume 1925.89(3) _computing_cell_refinement 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_data_collection 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_data_reduction 'CrysAlisPro 1.171.42.88a (Rigaku OD, 2023)' _computing_molecular_graphics 'Shelxtl-Plus/XP, Bruker AXS, Inc. 2009' _computing_publication_material 'Shelxtl-Plus, Bruker AXS, Inc. 2009' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.01(12) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -81.00 3.00 0.50 6.50 -- -47.20 105.00 29.00 168 2 \w 18.00 83.00 0.50 6.50 -- 47.20-105.00 -69.00 130 3 \w 37.00 107.00 0.50 26.00 -- 107.75-105.00 -69.00 140 4 \w 105.00 178.00 0.50 26.00 -- 107.75 105.00 29.00 146 5 \w -120.00 -32.00 0.50 6.50 -- -47.20 -57.00 -90.00 176 6 \w -86.00 -13.00 0.50 6.50 -- -47.20 125.00 60.00 146 7 \w -60.00 26.00 0.50 6.50 -- -47.20 38.00 30.00 172 8 \w 35.00 123.00 0.50 26.00 -- 107.75 -57.00 -60.00 176 9 \w 95.00 178.00 0.50 26.00 -- 107.75 38.00-180.00 166 10 \w 95.00 178.00 0.50 26.00 -- 107.75 19.00 30.00 166 11 \w 38.00 112.00 0.50 26.00 -- 107.75-125.00-120.00 148 12 \w 37.00 106.00 0.50 26.00 -- 107.75 -99.00 60.00 138 13 \w 35.00 120.00 0.50 26.00 -- 107.75 -38.00-120.00 170 14 \w 95.00 178.00 0.50 26.00 -- 107.75 38.00 90.00 166 15 \w 38.00 112.00 0.50 26.00 -- 107.75-125.00 90.00 148 16 \w 35.00 123.00 0.50 26.00 -- 107.75 -57.00 60.00 176 17 \w -120.00 -24.00 0.50 6.50 -- -47.20 -77.00 30.00 192 18 \w -120.00 -32.00 0.50 6.50 -- -47.20 -57.00 60.00 176 19 \w -120.00 -24.00 0.50 6.50 -- -47.20 -77.00 150.00 192 20 \w -120.00 -24.00 0.50 6.50 -- -47.20 -77.00 -30.00 192 21 \w -120.00 -24.00 0.50 6.50 -- -47.20 -77.00-120.00 192 22 \w 95.00 178.00 0.50 26.00 -- 107.75 19.00-120.00 166 23 \w 95.00 178.00 0.50 26.00 -- 107.75 19.00 -60.00 166 24 \w 95.00 178.00 0.50 26.00 -- 107.75 38.00 -30.00 166 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0638299000 _diffrn_orient_matrix_UB_12 0.0939262000 _diffrn_orient_matrix_UB_13 -0.0046709000 _diffrn_orient_matrix_UB_21 -0.1131250000 _diffrn_orient_matrix_UB_22 -0.0346492000 _diffrn_orient_matrix_UB_23 -0.0820224000 _diffrn_orient_matrix_UB_31 -0.0780436000 _diffrn_orient_matrix_UB_32 -0.0265727000 _diffrn_orient_matrix_UB_33 0.0903257000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0151 _diffrn_reflns_av_unetI/netI 0.0067 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 25979 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.999 _diffrn_reflns_theta_min 4.596 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.962 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84846 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.393 _exptl_crystal_description prism _exptl_crystal_F_000 840 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichloromethane, methanol' _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.171 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.431 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.043 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 272 _refine_ls_number_reflns 3983 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0343 _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^)+(0.0459P)^2^+1.0147P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0894 _refine_ls_wR_factor_ref 0.0895 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3942 _reflns_number_total 3983 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01552e2.cif _cod_data_source_block 1-ab-183a _cod_database_code 7160197 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C H N O Cl' _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. ; _shelx_estimated_absorpt_t_max 0.813 _shelx_estimated_absorpt_t_min 0.672 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C22(H22A,H22B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2A), C3(H3), C5(H5), C9(H9), C17(H17), C18(H18), C19(H19), C20(H20) 2.c Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C23(H23A,H23B,H23C) ; _shelx_res_file ; TITL 1-ab-183a_a.res in P2(1)/n 1-ab-183a.res created by SHELXL-2018/3 at 13:35:19 on 07-Apr-2023 REM Old TITL 1-AB-183A in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.136, Rweak 0.007, Alpha 0.026 REM 1.514 for 165 systematic absences, Orientation as input REM Formula found by SHELXT: C23 N4 O Cl CELL 1.54184 10.2648 14.8701 12.7374 90 97.874 90 ZERR 4 0.0001 0.0001 0.0001 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cl N O UNIT 92 72 4 12 8 L.S. 8 0 0 PLAN 5 SIZE 0.11 0.17 0.22 TEMP -173 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta REM REM REM WGHT 0.045900 1.014700 FVAR 0.50550 CL1 3 0.474770 0.789762 0.246023 11.00000 0.04810 0.01700 = 0.05037 0.00179 0.02776 0.00226 O1 5 0.636287 0.101351 0.142043 11.00000 0.03274 0.01826 = 0.03279 0.00257 0.01329 0.00182 O2 5 0.757563 0.125401 0.010251 11.00000 0.03445 0.02501 = 0.02817 -0.00299 0.01377 0.00378 N1 4 0.432976 0.410421 0.359993 11.00000 0.02350 0.01953 = 0.01942 0.00273 0.00871 0.00229 N2 4 0.709657 0.312954 0.026855 11.00000 0.03124 0.02121 = 0.02253 -0.00022 0.01427 0.00100 N3 4 0.410347 0.164813 0.347002 11.00000 0.02181 0.01682 = 0.01968 0.00267 0.00399 -0.00124 C1 1 0.436163 0.502473 0.345218 11.00000 0.01980 0.01939 = 0.01996 0.00172 0.00394 0.00230 C2 1 0.389530 0.570659 0.405170 11.00000 0.02378 0.02482 = 0.01988 0.00035 0.00656 0.00423 AFIX 43 H2A 2 0.347162 0.557145 0.465068 11.00000 -1.20000 AFIX 0 C3 1 0.406845 0.658592 0.374761 11.00000 0.02362 0.02124 = 0.02357 -0.00322 0.00532 0.00419 AFIX 43 H3 2 0.378040 0.706691 0.414950 11.00000 -1.20000 AFIX 0 C4 1 0.466809 0.676808 0.284767 11.00000 0.02504 0.01800 = 0.03129 0.00136 0.00685 0.00001 C5 1 0.515079 0.611130 0.224713 11.00000 0.02330 0.02051 = 0.02618 0.00226 0.00903 0.00022 AFIX 43 H5 2 0.556396 0.625975 0.164664 11.00000 -1.20000 AFIX 0 C6 1 0.501117 0.521030 0.255359 11.00000 0.01911 0.01949 = 0.02017 -0.00004 0.00508 0.00107 C7 1 0.537391 0.435267 0.217932 11.00000 0.01923 0.01863 = 0.02000 0.00033 0.00506 0.00019 C8 1 0.605686 0.387258 0.141194 11.00000 0.02152 0.01814 = 0.01999 -0.00022 0.00529 -0.00021 C9 1 0.673000 0.397060 0.055710 11.00000 0.03096 0.01822 = 0.02556 0.00101 0.01206 -0.00021 AFIX 43 H9 2 0.690858 0.452123 0.022650 11.00000 -1.20000 AFIX 0 C10 1 0.666417 0.248788 0.092416 11.00000 0.02247 0.01978 = 0.01885 0.00036 0.00535 -0.00031 C11 1 0.600715 0.293886 0.164266 11.00000 0.01841 0.01863 = 0.01771 -0.00002 0.00355 -0.00066 C12 1 0.530592 0.275450 0.260013 11.00000 0.01934 0.01764 = 0.01793 0.00032 0.00486 -0.00002 C13 1 0.494984 0.371644 0.283542 11.00000 0.01867 0.01922 = 0.01880 0.00035 0.00443 0.00088 C14 1 0.693436 0.154078 0.076031 11.00000 0.02198 0.02203 = 0.02017 -0.00064 0.00442 0.00051 C15 1 0.655766 0.005696 0.130911 11.00000 0.03611 0.01901 = 0.04629 0.00341 0.01112 0.00254 AFIX 137 H15A 2 0.616543 -0.013589 0.060005 11.00000 -1.50000 H15B 2 0.613792 -0.026556 0.184407 11.00000 -1.50000 H15C 2 0.750165 -0.007592 0.140776 11.00000 -1.50000 AFIX 0 C16 1 0.615141 0.231986 0.353660 11.00000 0.02177 0.01691 = 0.01740 -0.00138 0.00482 0.00300 C17 1 0.744565 0.248418 0.394229 11.00000 0.02153 0.02244 = 0.02239 -0.00419 0.00564 0.00051 AFIX 43 H17 2 0.794379 0.292311 0.362910 11.00000 -1.20000 AFIX 0 C18 1 0.800951 0.199052 0.482521 11.00000 0.02245 0.02712 = 0.02423 -0.00788 -0.00002 0.00580 AFIX 43 H18 2 0.890358 0.208657 0.510912 11.00000 -1.20000 AFIX 0 C19 1 0.726816 0.136280 0.528583 11.00000 0.03413 0.01777 = 0.02122 -0.00290 -0.00320 0.00757 AFIX 43 H19 2 0.766329 0.103206 0.588415 11.00000 -1.20000 AFIX 0 C20 1 0.594790 0.120567 0.488759 11.00000 0.03211 0.01626 = 0.02120 0.00089 0.00281 0.00117 AFIX 43 H20 2 0.543829 0.078260 0.521451 11.00000 -1.20000 AFIX 0 C21 1 0.540422 0.168939 0.399629 11.00000 0.02288 0.01532 = 0.01902 -0.00197 0.00419 0.00201 C22 1 0.410831 0.210645 0.243592 11.00000 0.02114 0.01919 = 0.01964 0.00316 0.00368 -0.00158 AFIX 23 H22A 2 0.328139 0.244586 0.223808 11.00000 -1.20000 H22B 2 0.420569 0.166418 0.187095 11.00000 -1.20000 AFIX 0 C23 1 0.350554 0.075590 0.336740 11.00000 0.02708 0.01812 = 0.02567 0.00337 0.00477 -0.00342 AFIX 137 H23A 2 0.399877 0.037427 0.293355 11.00000 -1.50000 H23B 2 0.259236 0.080745 0.302797 11.00000 -1.50000 H23C 2 0.352417 0.048714 0.407181 11.00000 -1.50000 AFIX 0 H2 2 0.752286 0.301362 -0.023892 11.00000 0.03261 H1 2 0.396959 0.384052 0.406099 11.00000 0.03397 HKLF 4 REM 1-ab-183a_a.res in P2(1)/n REM wR2 = 0.0895, GooF = S = 1.036, Restrained GooF = 1.036 for all data REM R1 = 0.0343 for 3942 Fo > 4sig(Fo) and 0.0345 for all 3983 data REM 272 parameters refined using 0 restraints END WGHT 0.0457 1.0230 REM Highest difference peak 0.431, deepest hole -0.267, 1-sigma level 0.043 Q1 1 0.3999 0.8211 0.2018 11.00000 0.05 0.43 Q2 1 0.5075 0.3214 0.2757 11.00000 0.05 0.30 Q3 1 0.5544 0.7944 0.2938 11.00000 0.05 0.29 Q4 1 0.5750 0.4201 0.1779 11.00000 0.05 0.28 Q5 1 0.6068 0.3415 0.1534 11.00000 0.05 0.28 ; _shelx_res_checksum 22855 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.230 _oxdiff_exptl_absorpt_empirical_full_min 0.840 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 Cl1 Cl 0.47477(4) 0.78976(2) 0.24602(3) 0.03653(12) Uani 1 1 d . . . . . O1 O 0.63629(9) 0.10135(6) 0.14204(8) 0.0271(2) Uani 1 1 d . . . . . O2 O 0.75756(9) 0.12540(6) 0.01025(7) 0.0283(2) Uani 1 1 d . . . . . N1 N 0.43298(10) 0.41042(7) 0.35999(8) 0.0203(2) Uani 1 1 d . . . . . N2 N 0.70966(11) 0.31295(7) 0.02686(9) 0.0240(2) Uani 1 1 d . . . . . N3 N 0.41035(10) 0.16481(7) 0.34700(8) 0.0193(2) Uani 1 1 d . . . . . C1 C 0.43616(11) 0.50247(8) 0.34522(9) 0.0196(2) Uani 1 1 d . . . . . C2 C 0.38953(12) 0.57066(9) 0.40517(10) 0.0225(3) Uani 1 1 d . . . . . H2A H 0.347162 0.557145 0.465068 0.027 Uiso 1 1 calc R U . . . C3 C 0.40684(12) 0.65859(9) 0.37476(10) 0.0226(3) Uani 1 1 d . . . . . H3 H 0.378040 0.706691 0.414950 0.027 Uiso 1 1 calc R U . . . C4 C 0.46681(13) 0.67681(9) 0.28477(11) 0.0245(3) Uani 1 1 d . . . . . C5 C 0.51508(12) 0.61113(9) 0.22471(10) 0.0228(3) Uani 1 1 d . . . . . H5 H 0.556396 0.625975 0.164664 0.027 Uiso 1 1 calc R U . . . C6 C 0.50112(12) 0.52103(8) 0.25536(9) 0.0194(2) Uani 1 1 d . . . . . C7 C 0.53739(11) 0.43527(8) 0.21793(9) 0.0191(2) Uani 1 1 d . . . . . C8 C 0.60569(12) 0.38726(8) 0.14119(10) 0.0197(2) Uani 1 1 d . . . . . C9 C 0.67300(13) 0.39706(9) 0.05571(10) 0.0242(3) Uani 1 1 d . . . . . H9 H 0.690858 0.452123 0.022650 0.029 Uiso 1 1 calc R U . . . C10 C 0.66642(12) 0.24879(8) 0.09242(9) 0.0201(2) Uani 1 1 d . . . . . C11 C 0.60071(11) 0.29389(8) 0.16427(9) 0.0182(2) Uani 1 1 d . . . . . C12 C 0.53059(11) 0.27545(8) 0.26001(9) 0.0181(2) Uani 1 1 d . . . . . C13 C 0.49498(11) 0.37164(8) 0.28354(9) 0.0187(2) Uani 1 1 d . . . . . C14 C 0.69344(12) 0.15408(8) 0.07603(10) 0.0213(2) Uani 1 1 d . . . . . C15 C 0.65577(15) 0.00570(9) 0.13091(13) 0.0333(3) Uani 1 1 d . . . . . H15A H 0.616543 -0.013589 0.060005 0.050 Uiso 1 1 calc R U . . . H15B H 0.613792 -0.026556 0.184407 0.050 Uiso 1 1 calc R U . . . H15C H 0.750165 -0.007592 0.140776 0.050 Uiso 1 1 calc R U . . . C16 C 0.61514(12) 0.23199(8) 0.35366(9) 0.0185(2) Uani 1 1 d . . . . . C17 C 0.74456(12) 0.24842(9) 0.39423(10) 0.0219(3) Uani 1 1 d . . . . . H17 H 0.794379 0.292311 0.362910 0.026 Uiso 1 1 calc R U . . . C18 C 0.80095(13) 0.19905(9) 0.48252(10) 0.0249(3) Uani 1 1 d . . . . . H18 H 0.890358 0.208657 0.510912 0.030 Uiso 1 1 calc R U . . . C19 C 0.72682(13) 0.13628(8) 0.52858(10) 0.0250(3) Uani 1 1 d . . . . . H19 H 0.766329 0.103206 0.588415 0.030 Uiso 1 1 calc R U . . . C20 C 0.59479(13) 0.12057(8) 0.48876(10) 0.0233(3) Uani 1 1 d . . . . . H20 H 0.543829 0.078260 0.521451 0.028 Uiso 1 1 calc R U . . . C21 C 0.54042(12) 0.16894(8) 0.39963(9) 0.0189(2) Uani 1 1 d . . . . . C22 C 0.41083(12) 0.21065(8) 0.24359(10) 0.0199(2) Uani 1 1 d . . . . . H22A H 0.328139 0.244586 0.223808 0.024 Uiso 1 1 calc R U . . . H22B H 0.420569 0.166418 0.187095 0.024 Uiso 1 1 calc R U . . . C23 C 0.35055(13) 0.07559(8) 0.33674(10) 0.0235(3) Uani 1 1 d . . . . . H23A H 0.399877 0.037427 0.293355 0.035 Uiso 1 1 calc R U . . . H23B H 0.259236 0.080745 0.302797 0.035 Uiso 1 1 calc R U . . . H23C H 0.352417 0.048714 0.407181 0.035 Uiso 1 1 calc R U . . . H2 H 0.7523(17) 0.3014(12) -0.0239(15) 0.033(4) Uiso 1 1 d . . . . . H1 H 0.3970(17) 0.3841(12) 0.4061(14) 0.034(5) Uiso 1 1 d . . . . . 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 Cl1 0.0481(2) 0.01700(17) 0.0504(2) 0.00179(13) 0.02776(17) 0.00226(13) O1 0.0327(5) 0.0183(4) 0.0328(5) 0.0026(4) 0.0133(4) 0.0018(4) O2 0.0344(5) 0.0250(5) 0.0282(5) -0.0030(4) 0.0138(4) 0.0038(4) N1 0.0235(5) 0.0195(5) 0.0194(5) 0.0027(4) 0.0087(4) 0.0023(4) N2 0.0312(6) 0.0212(5) 0.0225(5) -0.0002(4) 0.0143(5) 0.0010(4) N3 0.0218(5) 0.0168(5) 0.0197(5) 0.0027(4) 0.0040(4) -0.0012(4) C1 0.0198(5) 0.0194(6) 0.0200(6) 0.0017(4) 0.0039(4) 0.0023(4) C2 0.0238(6) 0.0248(6) 0.0199(6) 0.0004(5) 0.0066(5) 0.0042(5) C3 0.0236(6) 0.0212(6) 0.0236(6) -0.0032(5) 0.0053(5) 0.0042(5) C4 0.0250(6) 0.0180(6) 0.0313(7) 0.0014(5) 0.0069(5) 0.0000(5) C5 0.0233(6) 0.0205(6) 0.0262(6) 0.0023(5) 0.0090(5) 0.0002(5) C6 0.0191(5) 0.0195(6) 0.0202(6) 0.0000(4) 0.0051(4) 0.0011(4) C7 0.0192(5) 0.0186(6) 0.0200(5) 0.0003(4) 0.0051(4) 0.0002(4) C8 0.0215(6) 0.0181(6) 0.0200(6) -0.0002(4) 0.0053(4) -0.0002(4) C9 0.0310(6) 0.0182(6) 0.0256(6) 0.0010(5) 0.0121(5) -0.0002(5) C10 0.0225(6) 0.0198(6) 0.0189(5) 0.0004(4) 0.0054(4) -0.0003(5) C11 0.0184(5) 0.0186(6) 0.0177(5) 0.0000(4) 0.0035(4) -0.0007(4) C12 0.0193(6) 0.0176(6) 0.0179(5) 0.0003(4) 0.0049(4) 0.0000(4) C13 0.0187(5) 0.0192(6) 0.0188(5) 0.0004(4) 0.0044(4) 0.0009(4) C14 0.0220(6) 0.0220(6) 0.0202(6) -0.0006(5) 0.0044(5) 0.0005(5) C15 0.0361(7) 0.0190(6) 0.0463(8) 0.0034(6) 0.0111(6) 0.0025(5) C16 0.0218(6) 0.0169(5) 0.0174(5) -0.0014(4) 0.0048(4) 0.0030(4) C17 0.0215(6) 0.0224(6) 0.0224(6) -0.0042(5) 0.0056(5) 0.0005(5) C18 0.0225(6) 0.0271(6) 0.0242(6) -0.0079(5) 0.0000(5) 0.0058(5) C19 0.0341(7) 0.0178(6) 0.0212(6) -0.0029(5) -0.0032(5) 0.0076(5) C20 0.0321(6) 0.0163(5) 0.0212(6) 0.0009(4) 0.0028(5) 0.0012(5) C21 0.0229(6) 0.0153(5) 0.0190(5) -0.0020(4) 0.0042(4) 0.0020(4) C22 0.0211(6) 0.0192(6) 0.0196(6) 0.0032(4) 0.0037(4) -0.0016(4) C23 0.0271(6) 0.0181(6) 0.0257(6) 0.0034(5) 0.0048(5) -0.0034(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _citation_id _citation_doi _citation_year 1 10.1021/acs.orglett.3c03131 2023 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -4 -3 6 0.0705 2 -3 -8 0.0888 4 2 -7 0.0972 4 6 -4 0.0969 5 1 5 0.0477 -5 -1 -5 0.0627 -1 -2 8 0.0792 1 2 -8 0.0792 3 -6 -6 0.0876 -3 -8 3 0.0995 -2 8 4 0.0716 0 -5 7 0.0753 0 5 -7 0.0753 6 -2 -3 0.0927 -4 6 -4 0.0835 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 C14 O1 C15 115.79(10) . . ? C1 N1 H1 125.6(12) . . ? C13 N1 C1 107.44(10) . . ? C13 N1 H1 126.9(12) . . ? C9 N2 C10 110.22(10) . . ? C9 N2 H2 125.5(12) . . ? C10 N2 H2 124.3(12) . . ? C21 N3 C22 106.49(9) . . ? C21 N3 C23 116.16(10) . . ? C23 N3 C22 112.98(10) . . ? N1 C1 C2 129.02(11) . . ? N1 C1 C6 108.83(10) . . ? C2 C1 C6 122.13(11) . . ? C1 C2 H2A 121.0 . . ? C3 C2 C1 117.90(11) . . ? C3 C2 H2A 121.0 . . ? C2 C3 H3 120.0 . . ? C2 C3 C4 120.03(11) . . ? C4 C3 H3 120.0 . . ? C3 C4 Cl1 117.25(10) . . ? C5 C4 Cl1 119.29(10) . . ? C5 C4 C3 123.42(12) . . ? C4 C5 H5 121.2 . . ? C4 C5 C6 117.63(12) . . ? C6 C5 H5 121.2 . . ? C1 C6 C7 105.46(10) . . ? C5 C6 C1 118.84(11) . . ? C5 C6 C7 135.70(11) . . ? C6 C7 C8 145.94(11) . . ? C13 C7 C6 107.06(10) . . ? C13 C7 C8 106.93(10) . . ? C9 C8 C7 144.63(12) . . ? C9 C8 C11 107.66(11) . . ? C11 C8 C7 107.71(10) . . ? N2 C9 C8 107.57(11) . . ? N2 C9 H9 126.2 . . ? C8 C9 H9 126.2 . . ? N2 C10 C11 106.95(11) . . ? N2 C10 C14 119.90(11) . . ? C11 C10 C14 133.15(11) . . ? C8 C11 C12 112.06(10) . . ? C10 C11 C8 107.60(10) . . ? C10 C11 C12 140.31(11) . . ? C11 C12 C22 117.12(10) . . ? C13 C12 C11 98.14(9) . . ? C13 C12 C16 111.91(9) . . ? C13 C12 C22 113.83(10) . . ? C16 C12 C11 115.03(10) . . ? C16 C12 C22 101.43(9) . . ? N1 C13 C7 111.21(11) . . ? N1 C13 C12 133.59(11) . . ? C7 C13 C12 115.14(10) . . ? O1 C14 C10 111.54(10) . . ? O2 C14 O1 123.58(12) . . ? O2 C14 C10 124.87(12) . . ? O1 C15 H15A 109.5 . . ? O1 C15 H15B 109.5 . . ? O1 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C12 129.47(11) . . ? C17 C16 C21 121.34(11) . . ? C21 C16 C12 109.18(10) . . ? C16 C17 H17 120.7 . . ? C16 C17 C18 118.61(12) . . ? C18 C17 H17 120.7 . . ? C17 C18 H18 119.9 . . ? C19 C18 C17 120.21(12) . . ? C19 C18 H18 119.9 . . ? C18 C19 H19 119.3 . . ? C18 C19 C20 121.33(12) . . ? C20 C19 H19 119.3 . . ? C19 C20 H20 121.0 . . ? C21 C20 C19 117.94(12) . . ? C21 C20 H20 121.0 . . ? C16 C21 N3 111.71(10) . . ? C16 C21 C20 120.56(11) . . ? C20 C21 N3 127.70(11) . . ? N3 C22 C12 105.32(9) . . ? N3 C22 H22A 110.7 . . ? N3 C22 H22B 110.7 . . ? C12 C22 H22A 110.7 . . ? C12 C22 H22B 110.7 . . ? H22A C22 H22B 108.8 . . ? N3 C23 H23A 109.5 . . ? N3 C23 H23B 109.5 . . ? N3 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 Cl1 C4 1.7557(13) . ? O1 C14 1.3420(15) . ? O1 C15 1.4460(16) . ? O2 C14 1.2117(15) . ? N1 C1 1.3827(16) . ? N1 C13 1.3622(16) . ? N1 H1 0.834(19) . ? N2 C9 1.3707(16) . ? N2 C10 1.3807(16) . ? N2 H2 0.846(19) . ? N3 C21 1.4109(15) . ? N3 C22 1.4837(15) . ? N3 C23 1.4602(15) . ? C1 C2 1.3930(17) . ? C1 C6 1.4282(16) . ? C2 H2A 0.9500 . ? C2 C3 1.3821(18) . ? C3 H3 0.9500 . ? C3 C4 1.3998(18) . ? C4 C5 1.3741(18) . ? C5 H5 0.9500 . ? C5 C6 1.4083(17) . ? C6 C7 1.4286(17) . ? C7 C8 1.4643(17) . ? C7 C13 1.3721(17) . ? C8 C9 1.3749(17) . ? C8 C11 1.4216(16) . ? C9 H9 0.9500 . ? C10 C11 1.3825(17) . ? C10 C14 1.4559(17) . ? C11 C12 1.5235(16) . ? C12 C13 1.5164(16) . ? C12 C16 1.5199(16) . ? C12 C22 1.5534(16) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.3797(17) . ? C16 C21 1.3904(17) . ? C17 H17 0.9500 . ? C17 C18 1.4001(18) . ? C18 H18 0.9500 . ? C18 C19 1.385(2) . ? C19 H19 0.9500 . ? C19 C20 1.4001(19) . ? C20 H20 0.9500 . ? C20 C21 1.3943(17) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 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 Cl1 C4 C5 C6 -176.95(9) . . . . ? N1 C1 C2 C3 178.81(12) . . . . ? N1 C1 C6 C5 179.56(11) . . . . ? N1 C1 C6 C7 -0.46(13) . . . . ? N2 C10 C11 C8 -0.33(13) . . . . ? N2 C10 C11 C12 -177.66(14) . . . . ? N2 C10 C14 O1 -175.62(11) . . . . ? N2 C10 C14 O2 3.29(19) . . . . ? C1 N1 C13 C7 -0.82(14) . . . . ? C1 N1 C13 C12 176.13(12) . . . . ? C1 C2 C3 C4 1.49(18) . . . . ? C1 C6 C7 C8 -176.24(17) . . . . ? C1 C6 C7 C13 -0.03(13) . . . . ? C2 C1 C6 C5 -1.83(18) . . . . ? C2 C1 C6 C7 178.14(11) . . . . ? C2 C3 C4 Cl1 175.63(10) . . . . ? C2 C3 C4 C5 -2.3(2) . . . . ? C3 C4 C5 C6 0.9(2) . . . . ? C4 C5 C6 C1 1.07(18) . . . . ? C4 C5 C6 C7 -178.89(13) . . . . ? C5 C6 C7 C8 3.7(3) . . . . ? C5 C6 C7 C13 179.94(14) . . . . ? C6 C1 C2 C3 0.51(18) . . . . ? C6 C7 C8 C9 -3.3(3) . . . . ? C6 C7 C8 C11 176.53(17) . . . . ? C6 C7 C13 N1 0.53(14) . . . . ? C6 C7 C13 C12 -177.04(10) . . . . ? C7 C8 C9 N2 179.36(16) . . . . ? C7 C8 C11 C10 -179.39(10) . . . . ? C7 C8 C11 C12 -1.23(13) . . . . ? C8 C7 C13 N1 178.31(10) . . . . ? C8 C7 C13 C12 0.75(14) . . . . ? C8 C11 C12 C13 1.52(12) . . . . ? C8 C11 C12 C16 -117.35(11) . . . . ? C8 C11 C12 C22 123.64(11) . . . . ? C9 N2 C10 C11 0.07(14) . . . . ? C9 N2 C10 C14 179.58(11) . . . . ? C9 C8 C11 C10 0.48(14) . . . . ? C9 C8 C11 C12 178.64(10) . . . . ? C10 N2 C9 C8 0.23(15) . . . . ? C10 C11 C12 C13 178.77(15) . . . . ? C10 C11 C12 C16 59.9(2) . . . . ? C10 C11 C12 C22 -59.1(2) . . . . ? C11 C8 C9 N2 -0.43(14) . . . . ? C11 C10 C14 O1 3.73(19) . . . . ? C11 C10 C14 O2 -177.35(13) . . . . ? C11 C12 C13 N1 -178.23(13) . . . . ? C11 C12 C13 C7 -1.37(13) . . . . ? C11 C12 C16 C17 39.81(17) . . . . ? C11 C12 C16 C21 -141.29(11) . . . . ? C11 C12 C22 N3 148.54(10) . . . . ? C12 C16 C17 C18 179.77(11) . . . . ? C12 C16 C21 N3 -0.50(13) . . . . ? C12 C16 C21 C20 -178.81(11) . . . . ? C13 N1 C1 C2 -177.70(12) . . . . ? C13 N1 C1 C6 0.78(13) . . . . ? C13 C7 C8 C9 -179.48(18) . . . . ? C13 C7 C8 C11 0.31(13) . . . . ? C13 C12 C16 C17 -71.06(16) . . . . ? C13 C12 C16 C21 107.84(11) . . . . ? C13 C12 C22 N3 -97.87(11) . . . . ? C14 C10 C11 C8 -179.75(13) . . . . ? C14 C10 C11 C12 2.9(3) . . . . ? C15 O1 C14 O2 0.20(18) . . . . ? C15 O1 C14 C10 179.14(11) . . . . ? C16 C12 C13 N1 -57.02(17) . . . . ? C16 C12 C13 C7 119.84(11) . . . . ? C16 C12 C22 N3 22.49(11) . . . . ? C16 C17 C18 C19 -1.05(18) . . . . ? C17 C16 C21 N3 178.51(11) . . . . ? C17 C16 C21 C20 0.19(18) . . . . ? C17 C18 C19 C20 -0.06(19) . . . . ? C18 C19 C20 C21 1.22(19) . . . . ? C19 C20 C21 N3 -179.31(11) . . . . ? C19 C20 C21 C16 -1.28(18) . . . . ? C21 N3 C22 C12 -23.84(12) . . . . ? C21 C16 C17 C18 0.99(18) . . . . ? C22 N3 C21 C16 15.67(13) . . . . ? C22 N3 C21 C20 -166.16(12) . . . . ? C22 C12 C13 N1 57.26(17) . . . . ? C22 C12 C13 C7 -125.88(11) . . . . ? C22 C12 C16 C17 167.23(12) . . . . ? C22 C12 C16 C21 -13.87(12) . . . . ? C23 N3 C21 C16 142.46(11) . . . . ? C23 N3 C21 C20 -39.36(17) . . . . ? C23 N3 C22 C12 -152.52(10) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z -4.2584 -3.2059 6.4037 -0.0592 0.0676 0.9960 2.1186 -3.4692 -7.5438 -0.4258 0.4993 -0.7546 4.0221 1.9153 -7.0059 -0.0441 0.0533 -0.9976 4.3650 6.0785 -4.1613 0.3117 -0.3631 -0.8781 4.6281 0.9241 5.0536 -0.2322 -0.9701 0.0707 -4.6281 -0.9241 -5.0536 0.2322 0.9701 -0.0707 -1.0009 -1.9978 7.9963 -0.1611 -0.4734 0.8535 1.0009 1.9978 -7.9963 0.1611 0.4734 -0.8535 3.0011 -5.9975 -5.9956 -0.7269 0.3601 -0.6164 -2.9970 -7.9981 3.0003 -0.5739 0.3701 0.7174 -2.0017 7.9969 3.9962 0.8602 -0.3784 0.3047 -0.0005 -4.9964 6.9975 -0.5019 -0.4008 0.7649 0.0005 4.9964 -6.9975 0.5019 0.4008 -0.7649 5.9977 -1.9964 -2.9981 -0.5563 -0.3634 -0.6858 -3.9981 5.9944 -3.9992 0.8369 0.5726 -0.2085