#------------------------------------------------------------------------------ #$Date: 2025-01-06 15:53:48 +0200 (Mon, 06 Jan 2025) $ #$Revision: 297135 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160199.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_7160199 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_issue 48 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 9413 _journal_page_last 9425 _journal_paper_doi 10.1039/d4ob01552e _journal_volume 22 _journal_year 2024 _chemical_formula_moiety 'C15 H12 Br Cl N2 O4' _chemical_formula_sum 'C15 H12 Br Cl N2 O4' _chemical_formula_weight 399.63 _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 mixed _atom_sites_solution_primary dual _audit_block_doi 10.5517/ccdc.csd.cc2fhxd8 _audit_creation_date 2022-11-15 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2023-03-17 deposited with the CCDC. 2024-10-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 104.1410(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.45120(10) _cell_length_b 8.02230(10) _cell_length_c 14.9534(2) _cell_measurement_reflns_used 20055 _cell_measurement_temperature 100.1(4) _cell_measurement_theta_max 76.8570 _cell_measurement_theta_min 3.0670 _cell_volume 1564.72(3) _computing_cell_refinement 'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)' _computing_data_collection 'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)' _computing_data_reduction 'CrysAlisPro 1.171.41.120a (Rigaku OD, 2021)' _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 (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.1(4) _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 0.978 _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 -121.00 -37.00 0.50 6.00 -- -48.82 -41.00 20.00 168 2 \w 37.00 121.00 0.50 6.00 -- 48.82 41.00 173.00 168 3 \w -23.00 61.00 0.50 6.00 -- 48.82 -41.00 20.00 168 4 \w 35.00 120.00 0.50 24.00 -- 107.75 -41.00 20.00 170 5 \w 96.00 178.00 0.50 24.00 -- 107.75 41.00 173.00 164 6 \w -61.00 24.00 0.50 6.00 -- -48.82 41.00 173.00 170 7 \w 34.00 97.00 0.50 6.00 -- 48.82-125.00-120.00 126 8 \w 34.00 97.00 0.50 6.00 -- 48.82-125.00 60.00 126 9 \w 35.00 123.00 0.50 24.00 -- 107.75 -57.00 150.00 176 10 \w 32.00 121.00 0.50 24.00 -- 107.75 -19.00 0.00 178 11 \w 35.00 106.00 0.50 24.00 -- 107.75 -99.00-120.00 142 12 \w 35.00 112.00 0.50 24.00 -- 107.75-125.00-180.00 154 13 \w 35.00 106.00 0.50 24.00 -- 107.75 -99.00 30.00 142 14 \w 95.00 178.00 0.50 24.00 -- 107.75 19.00-150.00 166 15 \w 32.00 121.00 0.50 24.00 -- 107.75 -19.00-150.00 178 16 \w 35.00 112.00 0.50 24.00 -- 107.75-125.00 30.00 154 17 \w 35.00 112.00 0.50 24.00 -- 107.75-125.00-120.00 154 18 \w 35.00 120.00 0.50 24.00 -- 107.75 -38.00-150.00 170 19 \w -121.00 -34.00 0.50 6.00 -- -48.82 -57.00 -60.00 174 20 \w -121.00 -34.00 0.50 6.00 -- -48.82 -57.00 0.00 174 21 \w -121.00 -26.00 0.50 6.00 -- -48.82 -77.00 120.00 190 22 \w -121.00 -26.00 0.50 6.00 -- -48.82 -77.00-180.00 190 23 \w -121.00 -26.00 0.50 6.00 -- -48.82 -77.00 -60.00 190 24 \w -121.00 -26.00 0.50 6.00 -- -48.82 -77.00-120.00 190 25 \w 95.00 178.00 0.50 24.00 -- 107.75 19.00 30.00 166 26 \w 95.00 170.00 0.50 24.00 -- 107.75 38.00 -60.00 150 ; _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 0.0493815000 _diffrn_orient_matrix_UB_12 0.1723442000 _diffrn_orient_matrix_UB_13 -0.0040476000 _diffrn_orient_matrix_UB_21 0.1040185000 _diffrn_orient_matrix_UB_22 -0.0690987000 _diffrn_orient_matrix_UB_23 0.0545201000 _diffrn_orient_matrix_UB_31 0.0261264000 _diffrn_orient_matrix_UB_32 -0.0489447000 _diffrn_orient_matrix_UB_33 -0.0911992000 _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 0.0336 _diffrn_reflns_av_unetI/netI 0.0126 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.978 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 21679 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.978 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.235 _diffrn_reflns_theta_min 3.388 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 5.358 _exptl_absorpt_correction_T_max 0.973 _exptl_absorpt_correction_T_min 0.299 _exptl_absorpt_correction_type 'gaussian and multi-scan' _exptl_absorpt_process_details ; CrysAlisPro 1.171.41.120a (Rigaku Oxford Diffraction, 2021) Numerical absorption correction based on gaussian integration over a multifaceted crystal model 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 1.696 _exptl_crystal_description prism _exptl_crystal_F_000 800 _exptl_crystal_size_max 0.322 _exptl_crystal_size_mid 0.205 _exptl_crystal_size_min 0.143 _refine_diff_density_max 0.728 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.072 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 3240 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.099 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0276 _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^)+(0.0426P)^2^+1.4442P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0758 _refine_ls_wR_factor_ref 0.0758 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3238 _reflns_number_total 3240 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01552e2.cif _cod_data_source_block 1-ab-101b-1vl _cod_depositor_comments 'Adding full bibliography for 7160196--7160199.cif.' _cod_database_code 7160199 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C15 H12 N2 O4 Cl Br' _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C4(H4), C6(H6), C7(H7), C12(H12) 2.b Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C15(H15A,H15B,H15C) ; _shelx_res_file ; TITL 1-ab-101b-1vl_a.res in P2(1)/c 1-ab-101b-1vl.res created by SHELXL-2018/3 at 16:14:51 on 15-Nov-2022 REM Old TITL 1-AB-101B-1VL in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.095, Rweak 0.005, Alpha 0.035 REM 4.615 for 239 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N2 O4 Cl Br CELL 1.54184 13.4512 8.0223 14.9534 90 104.141 90 ZERR 4 0.0001 0.0001 0.0002 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br Cl N O UNIT 60 48 4 4 8 16 L.S. 4 0 0 PLAN 5 TEMP -173 CONF BOND list 4 MORE -1 BOND $H fmap 2 53 acta OMIT 14 1 6 OMIT 13 0 8 OMIT 13 1 8 REM REM REM WGHT 0.042600 1.444200 FVAR 2.86506 BR1 3 0.297901 0.209940 0.589664 11.00000 0.02311 0.01478 = 0.02687 0.00160 -0.00016 0.00137 CL1 4 0.655652 0.522982 0.626168 11.00000 0.01302 0.04961 = 0.02792 -0.00707 0.00680 -0.00123 O1 6 0.124486 0.667065 0.692687 11.00000 0.01368 0.03467 = 0.02651 -0.01274 0.00477 0.00012 O2 6 0.266803 0.809575 0.581098 11.00000 0.01666 0.01442 = 0.02847 0.00300 -0.00467 -0.00103 O3 6 0.088116 0.876842 0.468527 11.00000 0.01717 0.01995 = 0.02093 0.00041 0.00224 0.00230 O4 6 -0.018907 0.727847 0.358742 11.00000 0.01641 0.02814 = 0.01619 0.00098 0.00003 0.00380 N1 5 0.282613 0.557891 0.761617 11.00000 0.01565 0.02561 = 0.01648 -0.00076 0.00554 -0.00040 N2 5 0.065626 0.439533 0.415840 11.00000 0.01194 0.02366 = 0.01548 -0.00408 0.00343 -0.00226 C1 1 0.211620 0.625169 0.690844 11.00000 0.01543 0.01987 = 0.01838 -0.00680 0.00392 -0.00274 C2 1 0.260048 0.641140 0.605682 11.00000 0.01253 0.01586 = 0.01711 -0.00001 0.00165 -0.00098 C3 1 0.368265 0.581374 0.647013 11.00000 0.01376 0.01387 = 0.01525 -0.00056 0.00159 -0.00137 C4 1 0.453117 0.579800 0.610521 11.00000 0.01618 0.01857 = 0.01603 -0.00111 0.00284 -0.00259 AFIX 43 H4 2 0.449176 0.615478 0.549174 11.00000 -1.20000 AFIX 0 C5 1 0.544791 0.523536 0.667704 11.00000 0.01239 0.02073 = 0.02167 -0.00434 0.00383 -0.00182 C6 1 0.552952 0.469886 0.757322 11.00000 0.01516 0.01823 = 0.02160 -0.00118 -0.00135 0.00171 AFIX 43 H6 2 0.616431 0.428804 0.793279 11.00000 -1.20000 AFIX 0 C7 1 0.467420 0.476562 0.794415 11.00000 0.02056 0.01884 = 0.01626 0.00192 0.00084 0.00015 AFIX 43 H7 2 0.471379 0.442166 0.855979 11.00000 -1.20000 AFIX 0 C8 1 0.376989 0.534813 0.738594 11.00000 0.01524 0.01634 = 0.01637 0.00072 0.00323 -0.00147 C9 1 0.266630 0.525766 0.852881 11.00000 0.02858 0.04178 = 0.02058 0.00192 0.01314 -0.00215 AFIX 137 H9A 2 0.310688 0.599673 0.897862 11.00000 -1.50000 H9B 2 0.283756 0.409429 0.869928 11.00000 -1.50000 H9C 2 0.194684 0.546567 0.852303 11.00000 -1.50000 AFIX 0 C10 1 0.195270 0.533945 0.529648 11.00000 0.01348 0.01611 = 0.01408 0.00068 0.00505 -0.00015 C11 1 0.108294 0.581034 0.461273 11.00000 0.01178 0.02137 = 0.01287 -0.00185 0.00489 -0.00149 C12 1 0.119822 0.304420 0.451810 11.00000 0.01593 0.01946 = 0.01896 -0.00340 0.00656 -0.00295 AFIX 43 H12 2 0.105120 0.192216 0.432825 11.00000 -1.20000 AFIX 0 C13 1 0.200623 0.358463 0.521274 11.00000 0.01643 0.01603 = 0.01757 -0.00026 0.00552 -0.00065 C14 1 0.060471 0.742674 0.432329 11.00000 0.01040 0.02419 = 0.01306 0.00078 0.00422 0.00121 C15 1 -0.068711 0.883790 0.324164 11.00000 0.02258 0.03462 = 0.02164 0.00569 0.00200 0.00984 AFIX 137 H15A 2 -0.127943 0.860865 0.272749 11.00000 -1.50000 H15B 2 -0.020101 0.955258 0.302798 11.00000 -1.50000 H15C 2 -0.091674 0.940406 0.373627 11.00000 -1.50000 AFIX 0 H2A 2 0.006135 0.436987 0.375476 11.00000 0.02966 H2 2 0.214135 0.838855 0.553677 11.00000 0.03160 HKLF 4 REM 1-ab-101b-1vl_a.res in P2(1)/c REM wR2 = 0.0758, GooF = S = 1.099, Restrained GooF = 1.099 for all data REM R1 = 0.0276 for 3238 Fo > 4sig(Fo) and 0.0276 for all 3240 data REM 218 parameters refined using 0 restraints END WGHT 0.0426 1.4446 REM Highest difference peak 0.728, deepest hole -0.481, 1-sigma level 0.072 Q1 1 0.2561 0.2205 0.6269 11.00000 0.05 0.73 Q2 1 0.3507 0.2180 0.5620 11.00000 0.05 0.46 Q3 1 0.2321 0.6355 0.6465 11.00000 0.05 0.41 Q4 1 0.6041 0.5259 0.6516 11.00000 0.05 0.35 Q5 1 0.3778 0.5647 0.6953 11.00000 0.05 0.33 ; _shelx_res_checksum 71055 _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 2.079 _oxdiff_exptl_absorpt_empirical_full_min 0.513 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 Br1 Br 0.29790(2) 0.20994(2) 0.58966(2) 0.02267(9) Uani 1 1 d . . . . . Cl1 Cl 0.65565(3) 0.52298(7) 0.62617(3) 0.02987(13) Uani 1 1 d . . . . . O1 O 0.12449(10) 0.6671(2) 0.69269(10) 0.0250(3) Uani 1 1 d . . . . . O2 O 0.26680(11) 0.80957(16) 0.58110(10) 0.0216(3) Uani 1 1 d . . . . . O3 O 0.08812(10) 0.87684(17) 0.46853(9) 0.0198(3) Uani 1 1 d . . . . . O4 O -0.01891(10) 0.72785(17) 0.35874(9) 0.0209(3) Uani 1 1 d . . . . . N1 N 0.28261(11) 0.5579(2) 0.76162(10) 0.0190(3) Uani 1 1 d . . . . . N2 N 0.06563(12) 0.4395(2) 0.41584(10) 0.0170(3) Uani 1 1 d . . . . . C1 C 0.21162(13) 0.6252(2) 0.69084(12) 0.0179(3) Uani 1 1 d . . . . . C2 C 0.26005(13) 0.6411(2) 0.60568(12) 0.0155(3) Uani 1 1 d . . . . . C3 C 0.36826(13) 0.5814(2) 0.64701(12) 0.0146(3) Uani 1 1 d . . . . . C4 C 0.45312(13) 0.5798(2) 0.61052(12) 0.0171(3) Uani 1 1 d . . . . . H4 H 0.449176 0.615478 0.549174 0.021 Uiso 1 1 calc R U . . . C5 C 0.54479(13) 0.5235(2) 0.66770(13) 0.0183(4) Uani 1 1 d . . . . . C6 C 0.55295(14) 0.4699(2) 0.75732(13) 0.0193(4) Uani 1 1 d . . . . . H6 H 0.616431 0.428804 0.793279 0.023 Uiso 1 1 calc R U . . . C7 C 0.46742(14) 0.4766(2) 0.79441(13) 0.0192(4) Uani 1 1 d . . . . . H7 H 0.471379 0.442166 0.855979 0.023 Uiso 1 1 calc R U . . . C8 C 0.37699(13) 0.5348(2) 0.73859(12) 0.0161(3) Uani 1 1 d . . . . . C9 C 0.26663(17) 0.5258(3) 0.85288(14) 0.0291(5) Uani 1 1 d . . . . . H9A H 0.310688 0.599673 0.897862 0.044 Uiso 1 1 calc R U . . . H9B H 0.283756 0.409429 0.869928 0.044 Uiso 1 1 calc R U . . . H9C H 0.194684 0.546567 0.852303 0.044 Uiso 1 1 calc R U . . . C10 C 0.19527(13) 0.5339(2) 0.52965(11) 0.0143(3) Uani 1 1 d . . . . . C11 C 0.10829(13) 0.5810(2) 0.46127(11) 0.0150(3) Uani 1 1 d . . . . . C12 C 0.11982(14) 0.3044(2) 0.45181(13) 0.0177(4) Uani 1 1 d . . . . . H12 H 0.105120 0.192216 0.432825 0.021 Uiso 1 1 calc R U . . . C13 C 0.20062(13) 0.3585(2) 0.52127(12) 0.0164(3) Uani 1 1 d . . . . . C14 C 0.06047(13) 0.7427(2) 0.43233(12) 0.0156(3) Uani 1 1 d . . . . . C15 C -0.06871(16) 0.8838(3) 0.32416(14) 0.0269(4) Uani 1 1 d . . . . . H15A H -0.127943 0.860865 0.272749 0.040 Uiso 1 1 calc R U . . . H15B H -0.020101 0.955258 0.302798 0.040 Uiso 1 1 calc R U . . . H15C H -0.091674 0.940406 0.373627 0.040 Uiso 1 1 calc R U . . . H2A H 0.006(2) 0.437(3) 0.3755(19) 0.030(6) Uiso 1 1 d . . . . . H2 H 0.214(2) 0.839(4) 0.5537(19) 0.032(7) 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 Br1 0.02311(13) 0.01478(12) 0.02687(13) 0.00160(6) -0.00016(9) 0.00137(6) Cl1 0.0130(2) 0.0496(3) 0.0279(2) -0.0071(2) 0.00680(17) -0.00123(19) O1 0.0137(6) 0.0347(8) 0.0265(7) -0.0127(6) 0.0048(5) 0.0001(6) O2 0.0167(7) 0.0144(6) 0.0285(7) 0.0030(5) -0.0047(5) -0.0010(5) O3 0.0172(6) 0.0200(6) 0.0209(6) 0.0004(5) 0.0022(5) 0.0023(5) O4 0.0164(6) 0.0281(7) 0.0162(6) 0.0010(5) 0.0000(5) 0.0038(5) N1 0.0156(7) 0.0256(8) 0.0165(7) -0.0008(6) 0.0055(6) -0.0004(6) N2 0.0119(7) 0.0237(8) 0.0155(7) -0.0041(6) 0.0034(6) -0.0023(6) C1 0.0154(8) 0.0199(8) 0.0184(8) -0.0068(7) 0.0039(6) -0.0027(6) C2 0.0125(8) 0.0159(8) 0.0171(8) 0.0000(6) 0.0016(6) -0.0010(6) C3 0.0138(8) 0.0139(8) 0.0152(8) -0.0006(6) 0.0016(6) -0.0014(6) C4 0.0162(8) 0.0186(8) 0.0160(8) -0.0011(6) 0.0028(6) -0.0026(6) C5 0.0124(8) 0.0207(9) 0.0217(9) -0.0043(7) 0.0038(7) -0.0018(6) C6 0.0152(8) 0.0182(8) 0.0216(9) -0.0012(7) -0.0013(7) 0.0017(7) C7 0.0206(9) 0.0188(8) 0.0163(8) 0.0019(7) 0.0008(7) 0.0001(7) C8 0.0152(8) 0.0163(8) 0.0164(8) 0.0007(6) 0.0032(6) -0.0015(6) C9 0.0286(10) 0.0418(12) 0.0206(10) 0.0019(8) 0.0131(8) -0.0021(9) C10 0.0135(7) 0.0161(8) 0.0141(8) 0.0007(6) 0.0050(6) -0.0002(6) C11 0.0118(7) 0.0214(9) 0.0129(7) -0.0019(6) 0.0049(6) -0.0015(6) C12 0.0159(8) 0.0195(9) 0.0190(8) -0.0034(6) 0.0066(7) -0.0029(6) C13 0.0164(8) 0.0160(8) 0.0176(8) -0.0003(6) 0.0055(6) -0.0006(6) C14 0.0104(7) 0.0242(9) 0.0131(8) 0.0008(7) 0.0042(6) 0.0012(7) C15 0.0226(9) 0.0346(11) 0.0216(9) 0.0057(8) 0.0020(7) 0.0098(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' Br Br -0.6763 1.2805 '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 1 5 -5 0.1111 -3 -1 9 0.0946 0 -5 2 0.1236 8 -1 0 0.0590 -8 1 0 0.0840 -2 1 9 0.1102 4 0 -9 0.0832 -4 0 9 0.0932 2 -5 -4 0.1359 -4 -1 -7 0.1112 -3 5 3 0.1436 -6 0 -5 0.0936 6 0 5 0.0896 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 C2 O2 H2 109(2) . . ? C14 O4 C15 114.95(16) . . ? C1 N1 C8 111.59(15) . . ? C1 N1 C9 124.51(16) . . ? C8 N1 C9 123.72(16) . . ? C11 N2 H2A 124.1(18) . . ? C12 N2 C11 110.39(15) . . ? C12 N2 H2A 124.9(18) . . ? O1 C1 N1 126.01(17) . . ? O1 C1 C2 125.72(17) . . ? N1 C1 C2 108.27(14) . . ? O2 C2 C1 110.83(15) . . ? O2 C2 C3 107.06(14) . . ? O2 C2 C10 114.17(14) . . ? C3 C2 C1 101.01(13) . . ? C3 C2 C10 116.41(15) . . ? C10 C2 C1 106.56(13) . . ? C4 C3 C2 130.33(16) . . ? C4 C3 C8 120.38(16) . . ? C8 C3 C2 109.10(15) . . ? C3 C4 H4 121.5 . . ? C3 C4 C5 116.99(16) . . ? C5 C4 H4 121.5 . . ? C4 C5 Cl1 119.10(14) . . ? C6 C5 Cl1 117.99(14) . . ? C6 C5 C4 122.90(17) . . ? C5 C6 H6 120.2 . . ? C5 C6 C7 119.62(16) . . ? C7 C6 H6 120.2 . . ? C6 C7 H7 121.2 . . ? C8 C7 C6 117.64(17) . . ? C8 C7 H7 121.2 . . ? C3 C8 N1 109.89(15) . . ? C7 C8 N1 127.76(17) . . ? C7 C8 C3 122.35(17) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C2 128.03(16) . . ? C11 C10 C13 104.73(15) . . ? C13 C10 C2 126.62(16) . . ? N2 C11 C10 108.10(16) . . ? N2 C11 C14 119.00(15) . . ? C10 C11 C14 132.90(16) . . ? N2 C12 H12 126.3 . . ? N2 C12 C13 107.40(16) . . ? C13 C12 H12 126.3 . . ? C10 C13 Br1 128.78(14) . . ? C12 C13 Br1 121.85(13) . . ? C12 C13 C10 109.37(16) . . ? O3 C14 O4 122.56(17) . . ? O3 C14 C11 125.80(16) . . ? O4 C14 C11 111.64(16) . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 Br1 C13 1.8772(18) . ? Cl1 C5 1.7499(18) . ? O1 C1 1.226(2) . ? O2 C2 1.409(2) . ? O2 H2 0.76(3) . ? O3 C14 1.221(2) . ? O4 C14 1.338(2) . ? O4 C15 1.453(2) . ? N1 C1 1.353(2) . ? N1 C8 1.406(2) . ? N1 C9 1.455(2) . ? N2 C11 1.374(2) . ? N2 C12 1.343(2) . ? N2 H2A 0.88(3) . ? C1 C2 1.571(2) . ? C2 C3 1.514(2) . ? C2 C10 1.519(2) . ? C3 C4 1.380(2) . ? C3 C8 1.396(2) . ? C4 H4 0.9500 . ? C4 C5 1.393(2) . ? C5 C6 1.386(3) . ? C6 H6 0.9500 . ? C6 C7 1.395(3) . ? C7 H7 0.9500 . ? C7 C8 1.378(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.404(2) . ? C10 C13 1.417(2) . ? C11 C14 1.465(3) . ? C12 H12 0.9500 . ? C12 C13 1.377(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 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 C5 C6 C7 176.75(14) . . . . ? O1 C1 C2 O2 63.2(2) . . . . ? O1 C1 C2 C3 176.43(18) . . . . ? O1 C1 C2 C10 -61.5(2) . . . . ? O2 C2 C3 C4 -57.0(2) . . . . ? O2 C2 C3 C8 117.78(16) . . . . ? O2 C2 C10 C11 -32.7(2) . . . . ? O2 C2 C10 C13 157.74(17) . . . . ? N1 C1 C2 O2 -116.58(16) . . . . ? N1 C1 C2 C3 -3.38(18) . . . . ? N1 C1 C2 C10 118.67(16) . . . . ? N2 C11 C14 O3 177.30(16) . . . . ? N2 C11 C14 O4 -3.4(2) . . . . ? N2 C12 C13 Br1 -179.12(12) . . . . ? N2 C12 C13 C10 1.0(2) . . . . ? C1 N1 C8 C3 -2.8(2) . . . . ? C1 N1 C8 C7 176.91(18) . . . . ? C1 C2 C3 C4 -173.06(18) . . . . ? C1 C2 C3 C8 1.76(18) . . . . ? C1 C2 C10 C11 90.0(2) . . . . ? C1 C2 C10 C13 -79.6(2) . . . . ? C2 C3 C4 C5 176.98(17) . . . . ? C2 C3 C8 N1 0.4(2) . . . . ? C2 C3 C8 C7 -179.35(16) . . . . ? C2 C10 C11 N2 -171.29(16) . . . . ? C2 C10 C11 C14 9.5(3) . . . . ? C2 C10 C13 Br1 -9.0(3) . . . . ? C2 C10 C13 C12 170.88(16) . . . . ? C3 C2 C10 C11 -158.28(17) . . . . ? C3 C2 C10 C13 32.2(2) . . . . ? C3 C4 C5 Cl1 -178.61(13) . . . . ? C3 C4 C5 C6 0.3(3) . . . . ? C4 C3 C8 N1 175.78(16) . . . . ? C4 C3 C8 C7 -3.9(3) . . . . ? C4 C5 C6 C7 -2.2(3) . . . . ? C5 C6 C7 C8 1.0(3) . . . . ? C6 C7 C8 N1 -177.66(17) . . . . ? C6 C7 C8 C3 2.0(3) . . . . ? C8 N1 C1 O1 -175.92(18) . . . . ? C8 N1 C1 C2 3.9(2) . . . . ? C8 C3 C4 C5 2.7(3) . . . . ? C9 N1 C1 O1 -0.7(3) . . . . ? C9 N1 C1 C2 179.15(17) . . . . ? C9 N1 C8 C3 -178.09(18) . . . . ? C9 N1 C8 C7 1.6(3) . . . . ? C10 C2 C3 C4 72.0(2) . . . . ? C10 C2 C3 C8 -113.13(17) . . . . ? C10 C11 C14 O3 -3.5(3) . . . . ? C10 C11 C14 O4 175.76(17) . . . . ? C11 N2 C12 C13 -1.0(2) . . . . ? C11 C10 C13 Br1 179.48(13) . . . . ? C11 C10 C13 C12 -0.6(2) . . . . ? C12 N2 C11 C10 0.56(19) . . . . ? C12 N2 C11 C14 179.93(15) . . . . ? C13 C10 C11 N2 0.06(18) . . . . ? C13 C10 C11 C14 -179.19(18) . . . . ? C15 O4 C14 O3 1.0(2) . . . . ? C15 O4 C14 C11 -178.32(14) . . . . ? 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 0.5604 4.5665 -4.6311 0.8334 -0.5097 0.2135 -3.4910 -0.7112 9.4777 -0.3333 0.2027 -0.9208 0.4963 -5.0311 2.2372 -0.8516 0.5212 0.0552 8.4399 -0.5516 -0.0751 0.3220 0.9119 0.2544 -8.4399 0.5516 0.0751 -0.3220 -0.9119 -0.2544 -2.0001 1.0000 9.0003 0.0372 0.2135 -0.9220 4.0001 -0.0000 -9.0002 0.2340 -0.0746 0.9253 -4.0001 0.0000 9.0002 -0.2340 0.0746 -0.9253 1.9996 -5.0000 -3.9994 -0.7468 0.3354 0.6617 -3.9996 -1.0001 -7.0008 -0.3415 -0.7286 0.5829 -2.9996 4.9999 2.9992 0.7014 -0.4940 -0.5966 -5.9995 -0.0001 -5.0010 -0.2760 -0.8967 0.2993 5.9995 0.0001 5.0010 0.2760 0.8967 -0.2993