#------------------------------------------------------------------------------ #$Date: 2024-11-01 03:34:50 +0200 (Fri, 01 Nov 2024) $ #$Revision: 295709 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160198.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_7160198 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 'C15 H12 Br Cl N2 O4' _chemical_formula_sum 'C15 H12 Br Cl N2 O4' _chemical_formula_weight 399.63 _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 mixed _audit_block_doi 10.5517/ccdc.csd.cc2g0whw _audit_creation_date 2023-05-16 _audit_creation_method ; Olex2 1.5 (compiled 2021.07.19 svn.r715e62df for OlexSys, GUI svn.r6380) ; _audit_update_record ; 2023-05-23 deposited with the CCDC. 2024-10-28 downloaded from the CCDC. ; _cell_angle_alpha 73.634(4) _cell_angle_beta 81.798(3) _cell_angle_gamma 72.598(3) _cell_formula_units_Z 2 _cell_length_a 9.1305(3) _cell_length_b 9.5099(3) _cell_length_c 9.6003(4) _cell_measurement_reflns_used 12449 _cell_measurement_temperature 100.02(14) _cell_measurement_theta_max 76.6350 _cell_measurement_theta_min 4.8100 _cell_volume 761.66(5) _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)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.02(14) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.962 _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 -119.00 -61.00 0.50 4.50 -- -47.07-143.00 -25.00 116 2 \w -99.00 -22.00 0.50 4.50 -- -47.07 143.00 28.00 154 3 \w -88.00 -14.00 0.50 4.50 -- -47.07 127.00-140.00 148 4 \w -119.00 -72.00 0.50 4.50 -- -47.07-127.00 143.00 94 5 \w 36.00 96.00 0.50 4.50 -- 47.07-127.00 143.00 120 6 \w 44.00 105.00 0.50 4.50 -- 47.07-143.00 -25.00 122 7 \w 83.00 171.00 0.50 18.00 -- 107.75 143.00 28.00 176 8 \w 36.00 113.00 0.50 18.00 -- 107.75-127.00 143.00 154 9 \w 44.00 125.00 0.50 18.00 -- 107.75-143.00 -25.00 162 10 \w 94.00 178.00 0.50 18.00 -- 107.75 127.00-140.00 168 11 \w -119.00 -24.00 0.50 4.50 -- -47.07 -77.00 -30.00 190 12 \w -121.00 -34.00 0.50 4.50 -- -47.07 -19.00 0.00 174 13 \w -119.00 -73.00 0.50 4.50 -- -47.07-125.00 0.00 92 14 \w 35.00 120.00 0.50 18.00 -- 107.75 -38.00 120.00 170 15 \w 85.00 178.00 0.50 18.00 -- 107.75 77.00 30.00 186 16 \w 35.00 120.00 0.50 18.00 -- 107.75 -38.00 -90.00 170 17 \w 35.00 106.00 0.50 18.00 -- 107.75 -99.00 120.00 142 18 \w 35.00 106.00 0.50 18.00 -- 107.75 -99.00-150.00 142 19 \w 35.00 106.00 0.50 18.00 -- 107.75 -99.00 150.00 142 20 \w 35.00 106.00 0.50 18.00 -- 107.75 -99.00 -60.00 142 21 \w 93.00 178.00 0.50 18.00 -- 107.75 57.00-150.00 170 22 \w 95.00 178.00 0.50 18.00 -- 107.75 38.00 -60.00 166 23 \w 35.00 106.00 0.50 18.00 -- 107.75 -99.00 30.00 142 24 \w 35.00 123.00 0.50 18.00 -- 107.75 -57.00 -60.00 176 25 \w 95.00 178.00 0.50 18.00 -- 107.75 38.00 -30.00 166 26 \w -119.00 -24.00 0.50 4.50 -- -47.07 -77.00-150.00 190 27 \w -119.00 -24.00 0.50 4.50 -- -47.07 -77.00 120.00 190 28 \w -118.00 -32.00 0.50 4.50 -- -47.07 -57.00-120.00 172 29 \w -118.00 -32.00 0.50 4.50 -- -47.07 -57.00 150.00 172 30 \w -119.00 -73.00 0.50 4.50 -- -47.07-125.00-180.00 92 31 \w -119.00 -24.00 0.50 4.50 -- -47.07 -77.00 90.00 190 32 \w -119.00 -24.00 0.50 4.50 -- -47.07 -77.00 -60.00 190 33 \w -119.00 -24.00 0.50 4.50 -- -47.07 -77.00 30.00 190 34 \w 95.00 178.00 0.50 18.00 -- 107.75 38.00 90.00 166 35 \w 95.00 178.00 0.50 18.00 -- 107.75 19.00 150.00 166 ; _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 -0.0107940000 _diffrn_orient_matrix_UB_12 -0.0341925000 _diffrn_orient_matrix_UB_13 0.1672482000 _diffrn_orient_matrix_UB_21 -0.1755099000 _diffrn_orient_matrix_UB_22 0.0699013000 _diffrn_orient_matrix_UB_23 -0.0008109000 _diffrn_orient_matrix_UB_31 -0.0217618000 _diffrn_orient_matrix_UB_32 -0.1572873000 _diffrn_orient_matrix_UB_33 0.0106159000 _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 0.0193 _diffrn_reflns_av_unetI/netI 0.0096 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.962 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 12747 _diffrn_reflns_point_group_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.962 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.971 _diffrn_reflns_theta_min 4.811 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 5.503 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.56807 _exptl_absorpt_correction_type 'gaussian and multi-scan' _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.88a (Rigaku Oxford Diffraction, 2023) 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 1.742 _exptl_crystal_description prism _exptl_crystal_F_000 400 _exptl_crystal_size_max 0.309 _exptl_crystal_size_mid 0.242 _exptl_crystal_size_min 0.143 _refine_diff_density_max 0.411 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.063 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 3097 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.058 _refine_ls_R_factor_all 0.0237 _refine_ls_R_factor_gt 0.0237 _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^)+(0.0323P)^2^+0.8078P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0620 _refine_ls_wR_factor_ref 0.0620 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3096 _reflns_number_total 3097 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01552e2.cif _cod_data_source_block 1-ab-158a _cod_database_code 7160198 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula C15H12N2O4ClBr _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), C11(H11) 2.b Idealised Me refined as rotating group: C9(H9A,H9B,H9C), C15(H15A,H15B,H15C) ; _shelx_res_file ; TITL 1-ab-158a_auto_a.res in P-1 1-ab-158a.res created by SHELXL-2018/3 at 11:52:03 on 16-May-2023 REM Old TITL 1-AB-158A_auto in P1 REM SHELXT solution in P-1: R1 0.167, Rweak 0.014, Alpha 0.044 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C15 N2 O5 Br CELL 1.54184 9.130519 9.509911 9.60034 73.6341 81.7975 72.5978 ZERR 2 0.000303 0.000338 0.000418 0.0035 0.0031 0.0031 LATT 1 SFAC C H Br Cl N O UNIT 30 24 2 2 4 8 L.S. 10 PLAN 5 TEMP -173 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.032300 0.807800 FVAR 10.66096 BR1 3 0.578806 0.432766 0.693722 11.00000 0.01770 0.01402 = 0.01851 0.00025 0.00063 -0.00380 CL1 4 1.243902 0.335080 0.691692 11.00000 0.02632 0.02948 = 0.03798 0.00190 -0.01062 -0.01665 O1 6 0.610234 -0.009348 0.657840 11.00000 0.02037 0.02305 = 0.01776 -0.00427 -0.00101 -0.01006 O2 6 0.885105 -0.094430 0.837110 11.00000 0.01635 0.01275 = 0.02237 -0.00232 -0.00258 -0.00274 H2 2 0.835248 -0.144144 0.840295 11.00000 0.02454 O3 6 0.248291 0.334359 1.120148 11.00000 0.02079 0.01726 = 0.02430 -0.00523 0.00600 -0.00616 O4 6 0.317176 0.519439 0.943500 11.00000 0.01788 0.01329 = 0.02075 -0.00392 0.00183 -0.00264 N1 5 0.771259 0.126525 0.516739 11.00000 0.01796 0.01739 = 0.01499 -0.00399 -0.00036 -0.00501 N2 5 0.532517 0.133364 1.080974 11.00000 0.01679 0.01648 = 0.01347 -0.00277 0.00006 -0.00573 H2A 2 0.493121 0.104720 1.156826 11.00000 0.02532 C1 1 0.712643 0.053031 0.644216 11.00000 0.01675 0.01331 = 0.01633 -0.00435 -0.00073 -0.00165 C2 1 0.800275 0.056782 0.770730 11.00000 0.01409 0.01330 = 0.01600 -0.00239 -0.00162 -0.00306 C3 1 0.910373 0.146937 0.687912 11.00000 0.01411 0.01267 = 0.01788 -0.00339 0.00129 -0.00182 C4 1 1.018482 0.192738 0.737803 11.00000 0.01504 0.01593 = 0.02035 -0.00351 -0.00153 -0.00211 AFIX 43 H4 2 1.032768 0.169478 0.838713 11.00000 -1.20000 AFIX 0 C5 1 1.106013 0.274684 0.633844 11.00000 0.01614 0.01655 = 0.02980 -0.00402 -0.00288 -0.00568 C6 1 1.087358 0.309424 0.485938 11.00000 0.02026 0.01885 = 0.02586 -0.00155 0.00397 -0.00781 AFIX 43 H6 2 1.149927 0.364375 0.418313 11.00000 -1.20000 AFIX 0 C7 1 0.976933 0.263844 0.436306 11.00000 0.02120 0.01919 = 0.01895 -0.00398 0.00195 -0.00514 AFIX 43 H7 2 0.961971 0.287389 0.335511 11.00000 -1.20000 AFIX 0 C8 1 0.890040 0.182989 0.539639 11.00000 0.01596 0.01379 = 0.02035 -0.00489 0.00028 -0.00260 C9 1 0.715907 0.145694 0.375960 11.00000 0.02487 0.02262 = 0.01566 -0.00409 -0.00277 -0.00683 AFIX 137 H9A 2 0.800639 0.099630 0.313715 11.00000 -1.50000 H9B 2 0.676388 0.254515 0.330051 11.00000 -1.50000 H9C 2 0.633406 0.095851 0.389275 11.00000 -1.50000 AFIX 0 C10 1 0.688001 0.125187 0.880850 11.00000 0.01383 0.01488 = 0.01656 -0.00371 -0.00264 -0.00431 C11 1 0.653208 0.044450 1.019434 11.00000 0.01470 0.01569 = 0.01677 -0.00334 -0.00270 -0.00418 AFIX 43 H11 2 0.705991 -0.057549 1.064219 11.00000 -1.20000 AFIX 0 C12 1 0.484469 0.273471 0.985696 11.00000 0.01543 0.01418 = 0.01651 -0.00286 -0.00170 -0.00557 C13 1 0.582037 0.271428 0.861156 11.00000 0.01618 0.01344 = 0.01433 -0.00111 -0.00191 -0.00530 C14 1 0.339956 0.376987 1.024048 11.00000 0.01834 0.01531 = 0.01683 -0.00570 -0.00223 -0.00571 C15 1 0.171135 0.621538 0.976769 11.00000 0.01938 0.01695 = 0.02379 -0.00442 0.00183 -0.00011 AFIX 137 H15A 2 0.156241 0.610573 1.082027 11.00000 -1.50000 H15B 2 0.087651 0.596215 0.943843 11.00000 -1.50000 H15C 2 0.170788 0.726846 0.926926 11.00000 -1.50000 AFIX 0 HKLF 4 REM 1-ab-158a_auto_a.res in P-1 REM wR2 = 0.0620, GooF = S = 1.058, Restrained GooF = 1.058 for all data REM R1 = 0.0237 for 3096 Fo > 4sig(Fo) and 0.0237 for all 3097 data REM 218 parameters refined using 0 restraints END WGHT 0.0307 0.8099 REM Highest difference peak 0.411, deepest hole -0.446, 1-sigma level 0.063 Q1 1 0.6293 0.1964 0.8559 11.00000 0.05 0.41 Q2 1 0.8636 0.1044 0.7383 11.00000 0.05 0.38 Q3 1 0.5710 0.3810 0.5954 11.00000 0.05 0.34 Q4 1 1.0809 0.2257 0.6843 11.00000 0.05 0.34 Q5 1 0.5969 0.3160 0.7956 11.00000 0.05 0.33 ; _shelx_res_checksum 55807 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: ; _oxdiff_exptl_absorpt_empirical_full_max 1.322 _oxdiff_exptl_absorpt_empirical_full_min 0.833 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 Br1 Br 0.57881(2) 0.43277(2) 0.69372(2) 0.01798(7) Uani 1 1 d . . . . . Cl1 Cl 1.24390(6) 0.33508(6) 0.69169(6) 0.03054(12) Uani 1 1 d . . . . . O1 O 0.61023(15) -0.00935(15) 0.65784(13) 0.0197(3) Uani 1 1 d . . . . . O2 O 0.88510(15) -0.09443(14) 0.83711(14) 0.0177(3) Uani 1 1 d . . . . . H2 H 0.835(3) -0.144(3) 0.840(3) 0.025(7) Uiso 1 1 d . . . . . O3 O 0.24829(15) 0.33436(15) 1.12015(14) 0.0213(3) Uani 1 1 d . . . . . O4 O 0.31718(14) 0.51944(14) 0.94350(14) 0.0181(3) Uani 1 1 d . . . . . N1 N 0.77126(17) 0.12652(17) 0.51674(16) 0.0168(3) Uani 1 1 d . . . . . N2 N 0.53252(17) 0.13336(17) 1.08097(17) 0.0156(3) Uani 1 1 d . . . . . H2A H 0.493(3) 0.105(3) 1.157(3) 0.025(6) Uiso 1 1 d . . . . . C1 C 0.7126(2) 0.05303(19) 0.64422(19) 0.0159(3) Uani 1 1 d . . . . . C2 C 0.80027(19) 0.05678(19) 0.77073(18) 0.0148(3) Uani 1 1 d . . . . . C3 C 0.91037(19) 0.14694(19) 0.68791(19) 0.0156(3) Uani 1 1 d . . . . . C4 C 1.0185(2) 0.1927(2) 0.7378(2) 0.0178(3) Uani 1 1 d . . . . . H4 H 1.032768 0.169478 0.838713 0.021 Uiso 1 1 calc R U . . . C5 C 1.1060(2) 0.2747(2) 0.6338(2) 0.0208(4) Uani 1 1 d . . . . . C6 C 1.0874(2) 0.3094(2) 0.4859(2) 0.0225(4) Uani 1 1 d . . . . . H6 H 1.149927 0.364375 0.418313 0.027 Uiso 1 1 calc R U . . . C7 C 0.9769(2) 0.2638(2) 0.4363(2) 0.0204(4) Uani 1 1 d . . . . . H7 H 0.961971 0.287389 0.335511 0.024 Uiso 1 1 calc R U . . . C8 C 0.8900(2) 0.1830(2) 0.5396(2) 0.0171(3) Uani 1 1 d . . . . . C9 C 0.7159(2) 0.1457(2) 0.37596(19) 0.0210(4) Uani 1 1 d . . . . . H9A H 0.800639 0.099630 0.313715 0.031 Uiso 1 1 calc R U . . . H9B H 0.676388 0.254515 0.330051 0.031 Uiso 1 1 calc R U . . . H9C H 0.633406 0.095851 0.389275 0.031 Uiso 1 1 calc R U . . . C10 C 0.68800(19) 0.12519(19) 0.88085(19) 0.0149(3) Uani 1 1 d . . . . . C11 C 0.65321(19) 0.04445(19) 1.01943(19) 0.0157(3) Uani 1 1 d . . . . . H11 H 0.705991 -0.057549 1.064219 0.019 Uiso 1 1 calc R U . . . C12 C 0.4845(2) 0.27347(19) 0.98570(19) 0.0152(3) Uani 1 1 d . . . . . C13 C 0.58204(19) 0.27143(19) 0.86116(18) 0.0148(3) Uani 1 1 d . . . . . C14 C 0.3400(2) 0.3770(2) 1.02405(19) 0.0161(3) Uani 1 1 d . . . . . C15 C 0.1711(2) 0.6215(2) 0.9768(2) 0.0216(4) Uani 1 1 d . . . . . H15A H 0.156241 0.610573 1.082027 0.032 Uiso 1 1 calc R U . . . H15B H 0.087651 0.596215 0.943843 0.032 Uiso 1 1 calc R U . . . H15C H 0.170788 0.726846 0.926926 0.032 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 Br1 0.01770(10) 0.01402(11) 0.01851(11) 0.00025(7) 0.00063(7) -0.00380(7) Cl1 0.0263(2) 0.0295(3) 0.0380(3) 0.0019(2) -0.0106(2) -0.01665(19) O1 0.0204(6) 0.0230(7) 0.0178(6) -0.0043(5) -0.0010(5) -0.0101(5) O2 0.0163(6) 0.0127(6) 0.0224(6) -0.0023(5) -0.0026(5) -0.0027(5) O3 0.0208(6) 0.0173(6) 0.0243(7) -0.0052(5) 0.0060(5) -0.0062(5) O4 0.0179(6) 0.0133(6) 0.0208(6) -0.0039(5) 0.0018(5) -0.0026(5) N1 0.0180(7) 0.0174(7) 0.0150(7) -0.0040(6) -0.0004(5) -0.0050(6) N2 0.0168(7) 0.0165(7) 0.0135(7) -0.0028(6) 0.0001(6) -0.0057(6) C1 0.0167(8) 0.0133(8) 0.0163(8) -0.0044(6) -0.0007(6) -0.0016(6) C2 0.0141(7) 0.0133(8) 0.0160(8) -0.0024(6) -0.0016(6) -0.0031(6) C3 0.0141(8) 0.0127(8) 0.0179(8) -0.0034(6) 0.0013(6) -0.0018(6) C4 0.0150(8) 0.0159(8) 0.0203(8) -0.0035(7) -0.0015(6) -0.0021(6) C5 0.0161(8) 0.0165(8) 0.0298(10) -0.0040(7) -0.0029(7) -0.0057(7) C6 0.0203(9) 0.0188(9) 0.0259(10) -0.0016(7) 0.0040(7) -0.0078(7) C7 0.0212(9) 0.0192(9) 0.0190(9) -0.0040(7) 0.0020(7) -0.0051(7) C8 0.0160(8) 0.0138(8) 0.0204(8) -0.0049(7) 0.0003(6) -0.0026(6) C9 0.0249(9) 0.0226(9) 0.0157(8) -0.0041(7) -0.0028(7) -0.0068(7) C10 0.0138(7) 0.0149(8) 0.0166(8) -0.0037(6) -0.0026(6) -0.0043(6) C11 0.0147(8) 0.0157(8) 0.0168(8) -0.0033(6) -0.0027(6) -0.0042(6) C12 0.0154(8) 0.0142(8) 0.0165(8) -0.0029(6) -0.0017(6) -0.0056(6) C13 0.0162(8) 0.0134(8) 0.0143(8) -0.0011(6) -0.0019(6) -0.0053(6) C14 0.0183(8) 0.0153(8) 0.0168(8) -0.0057(6) -0.0022(6) -0.0057(7) C15 0.0194(9) 0.0169(9) 0.0238(9) -0.0044(7) 0.0018(7) -0.0001(7) 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 -4 -2 -5 0.0614 -1 4 -2 0.1184 1 6 0 0.1244 3 6 2 0.1394 4 0 5 0.0552 -4 -5 0 0.1405 1 -5 -4 0.1198 2 -3 -5 0.1208 4 5 -1 0.1385 0 5 4 0.1173 -4 0 4 0.1068 4 -1 4 0.0477 6 2 2 0.0970 -6 -2 -2 0.0970 5 -2 2 0.0675 -5 2 -2 0.0755 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 106(2) . . ? C14 O4 C15 114.33(14) . . ? C1 N1 C8 111.01(14) . . ? C1 N1 C9 123.68(15) . . ? C8 N1 C9 125.30(15) . . ? C11 N2 H2A 123.5(19) . . ? C11 N2 C12 109.93(15) . . ? C12 N2 H2A 126.4(19) . . ? O1 C1 N1 125.57(16) . . ? O1 C1 C2 125.59(16) . . ? N1 C1 C2 108.81(14) . . ? O2 C2 C1 109.10(14) . . ? O2 C2 C3 109.40(14) . . ? O2 C2 C10 110.49(14) . . ? C3 C2 C1 101.10(13) . . ? C10 C2 C1 110.10(13) . . ? C10 C2 C3 116.15(14) . . ? C4 C3 C2 130.16(16) . . ? C4 C3 C8 120.67(16) . . ? C8 C3 C2 109.17(15) . . ? C3 C4 H4 121.4 . . ? C3 C4 C5 117.23(17) . . ? C5 C4 H4 121.4 . . ? C4 C5 Cl1 118.88(15) . . ? C6 C5 Cl1 118.80(14) . . ? C6 C5 C4 122.31(17) . . ? C5 C6 H6 119.9 . . ? C5 C6 C7 120.16(17) . . ? C7 C6 H6 119.9 . . ? C6 C7 H7 121.3 . . ? C8 C7 C6 117.40(17) . . ? C8 C7 H7 121.3 . . ? C3 C8 N1 109.87(15) . . ? C7 C8 N1 127.90(17) . . ? C7 C8 C3 122.22(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 124.47(15) . . ? C11 C10 C13 105.86(15) . . ? C13 C10 C2 129.01(15) . . ? N2 C11 C10 109.21(15) . . ? N2 C11 H11 125.4 . . ? C10 C11 H11 125.4 . . ? N2 C12 C13 106.78(15) . . ? N2 C12 C14 117.72(15) . . ? C13 C12 C14 134.77(16) . . ? C10 C13 Br1 124.84(13) . . ? C12 C13 Br1 126.96(13) . . ? C12 C13 C10 108.20(15) . . ? O3 C14 O4 123.62(16) . . ? O3 C14 C12 122.39(16) . . ? O4 C14 C12 113.97(15) . . ? 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 1.8803(17) . ? Cl1 C5 1.7422(19) . ? O1 C1 1.223(2) . ? O2 H2 0.74(3) . ? O2 C2 1.426(2) . ? O3 C14 1.220(2) . ? O4 C14 1.328(2) . ? O4 C15 1.450(2) . ? N1 C1 1.352(2) . ? N1 C8 1.413(2) . ? N1 C9 1.455(2) . ? N2 H2A 0.78(3) . ? N2 C11 1.348(2) . ? N2 C12 1.372(2) . ? C1 C2 1.561(2) . ? C2 C3 1.510(2) . ? C2 C10 1.507(2) . ? C3 C4 1.380(2) . ? C3 C8 1.393(2) . ? C4 H4 0.9500 . ? C4 C5 1.396(3) . ? C5 C6 1.388(3) . ? C6 H6 0.9500 . ? C6 C7 1.395(3) . ? C7 H7 0.9500 . ? C7 C8 1.384(3) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.382(2) . ? C10 C13 1.416(2) . ? C11 H11 0.9500 . ? C12 C13 1.386(2) . ? C12 C14 1.461(2) . ? 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 -179.41(15) . . . . ? O1 C1 C2 O2 64.4(2) . . . . ? O1 C1 C2 C3 179.63(16) . . . . ? O1 C1 C2 C10 -57.0(2) . . . . ? O2 C2 C3 C4 -66.4(2) . . . . ? O2 C2 C3 C8 113.45(16) . . . . ? O2 C2 C10 C11 -10.4(2) . . . . ? O2 C2 C10 C13 -179.81(16) . . . . ? N1 C1 C2 O2 -113.98(15) . . . . ? N1 C1 C2 C3 1.24(17) . . . . ? N1 C1 C2 C10 124.61(15) . . . . ? N2 C12 C13 Br1 -177.83(12) . . . . ? N2 C12 C13 C10 1.74(19) . . . . ? N2 C12 C14 O3 -14.3(3) . . . . ? N2 C12 C14 O4 166.78(15) . . . . ? C1 N1 C8 C3 -0.5(2) . . . . ? C1 N1 C8 C7 -179.98(17) . . . . ? C1 C2 C3 C4 178.62(17) . . . . ? C1 C2 C3 C8 -1.55(17) . . . . ? C1 C2 C10 C11 110.15(18) . . . . ? C1 C2 C10 C13 -59.2(2) . . . . ? C2 C3 C4 C5 179.32(17) . . . . ? C2 C3 C8 N1 1.38(19) . . . . ? C2 C3 C8 C7 -179.14(16) . . . . ? C2 C10 C11 N2 -170.57(15) . . . . ? C2 C10 C13 Br1 -11.1(3) . . . . ? C2 C10 C13 C12 169.30(16) . . . . ? C3 C2 C10 C11 -135.77(17) . . . . ? C3 C2 C10 C13 54.8(2) . . . . ? C3 C4 C5 Cl1 179.95(13) . . . . ? C3 C4 C5 C6 -0.2(3) . . . . ? C4 C3 C8 N1 -178.77(15) . . . . ? C4 C3 C8 C7 0.7(3) . . . . ? C4 C5 C6 C7 0.8(3) . . . . ? C5 C6 C7 C8 -0.5(3) . . . . ? C6 C7 C8 N1 179.21(17) . . . . ? C6 C7 C8 C3 -0.2(3) . . . . ? C8 N1 C1 O1 -178.89(16) . . . . ? C8 N1 C1 C2 -0.51(19) . . . . ? C8 C3 C4 C5 -0.5(3) . . . . ? C9 N1 C1 O1 2.0(3) . . . . ? C9 N1 C1 C2 -179.61(15) . . . . ? C9 N1 C8 C3 178.54(16) . . . . ? C9 N1 C8 C7 -0.9(3) . . . . ? C10 C2 C3 C4 59.5(2) . . . . ? C10 C2 C3 C8 -120.66(16) . . . . ? C11 N2 C12 C13 -1.22(19) . . . . ? C11 N2 C12 C14 170.46(14) . . . . ? C11 C10 C13 Br1 177.97(12) . . . . ? C11 C10 C13 C12 -1.61(19) . . . . ? C12 N2 C11 C10 0.20(19) . . . . ? C13 C10 C11 N2 0.87(19) . . . . ? C13 C12 C14 O3 154.40(19) . . . . ? C13 C12 C14 O4 -24.5(3) . . . . ? C14 C12 C13 Br1 12.6(3) . . . . ? C14 C12 C13 C10 -167.86(18) . . . . ? C15 O4 C14 O3 -1.3(2) . . . . ? C15 O4 C14 C12 177.55(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 -4.4312 -2.0147 -4.7431 -0.6766 0.6407 0.3630 -1.1393 4.3273 -2.3638 -0.5310 0.5044 -0.6809 1.1144 5.8806 -0.0764 -0.2259 0.2155 -0.9500 3.1377 5.9501 2.2902 0.1457 -0.1366 -0.9798 3.9488 0.1452 4.6166 0.7245 -0.6867 -0.0598 -3.5503 -5.3506 0.4257 0.2925 0.2488 0.9234 0.9674 -4.6170 -4.2944 -0.5708 -0.4890 0.6595 2.4529 -2.7022 -4.6954 -0.7194 -0.6156 0.3218 3.6904 5.1346 -0.7363 -0.3385 -0.2882 -0.8957 -0.4043 5.1298 3.9959 0.4973 0.4263 -0.7556 -3.6360 0.1721 4.3234 0.7564 0.6467 0.0979 4.0080 -0.7352 3.9848 0.6483 -0.7581 0.0707 5.7542 1.9025 2.3174 0.2604 -0.8788 -0.3999 -5.7542 -1.9025 -2.3174 -0.2604 0.8788 0.3999 4.7610 -1.5636 1.6682 0.2811 -0.9462 0.1600 -4.7610 1.5636 -1.6682 -0.2811 0.9462 -0.1600