#------------------------------------------------------------------------------ #$Date: 2024-01-06 10:22:26 +0200 (Sat, 06 Jan 2024) $ #$Revision: 288818 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247725.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_7247725 loop_ _publ_author_name 'Pan, Dongping' 'Liu, Fu-Xiaomin' 'Zeng, Zhongyi' 'Ye, Junwei' 'Cai, Ying' 'Wang, Shengdong' 'Zhou, Zhi' 'Yi, Wei' _publ_section_title ; Practical conversion of gem-difluorocyclopropenes for the chemodivergent assembly of fluorinated heterocyclic frameworks ; _journal_issue 24 _journal_name_full 'Green Chemistry' _journal_page_first 10630 _journal_page_last 10637 _journal_paper_doi 10.1039/D3GC03203E _journal_volume 25 _journal_year 2023 _chemical_formula_moiety 'C21 H17 Br F2 N2 O' _chemical_formula_sum 'C21 H17 Br F2 N2 O' _chemical_formula_weight 431.27 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2023-04-24 _audit_creation_method ; Olex2 1.5-beta (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439) ; _audit_update_record ; 2023-07-07 deposited with the CCDC. 2023-11-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.294(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.5594(7) _cell_length_b 19.9216(15) _cell_length_c 10.3113(8) _cell_measurement_reflns_used 3205 _cell_measurement_temperature 220.03(10) _cell_measurement_theta_max 26.3590 _cell_measurement_theta_min 2.9160 _cell_volume 1841.8(3) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5-beta (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-beta (Dolomanov et al., 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 220.03(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 -84.00 -49.00 1.00 5.00 -- -11.27 -57.00 -90.00 35 2 \w -33.00 32.00 1.00 5.00 -- 11.90 -38.00 120.00 65 3 \w -20.00 84.00 1.00 5.00 -- 11.90 77.00 60.00 104 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0611620000 _diffrn_orient_matrix_UB_12 -0.0003240000 _diffrn_orient_matrix_UB_13 0.0632803000 _diffrn_orient_matrix_UB_21 0.0052708000 _diffrn_orient_matrix_UB_22 -0.0353916000 _diffrn_orient_matrix_UB_23 -0.0048499000 _diffrn_orient_matrix_UB_31 0.0498448000 _diffrn_orient_matrix_UB_32 0.0041191000 _diffrn_orient_matrix_UB_33 -0.0367325000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0368 _diffrn_reflns_av_unetI/netI 0.0500 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 8451 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 2.045 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 2.265 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.67432 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'light colourless' _exptl_crystal_density_diffrn 1.555 _exptl_crystal_description block _exptl_crystal_F_000 872 _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.624 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.072 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 3249 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0546 _refine_ls_R_factor_gt 0.0372 _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^)+(0.0391P)^2^+0.3064P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0795 _refine_ls_wR_factor_ref 0.0874 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2550 _reflns_number_total 3249 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03203e2.cif _cod_data_source_block 120-9 _cod_depositor_comments 'Adding full bibliography for 7247725--7247728.cif.' _cod_database_code 7247725 _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. ; _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 Ternary CH refined with riding coordinates: C7(H7), C10(H10) 2.b Secondary CH2 refined with riding coordinates: C14(H14A,H14B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C11(H11), C12(H12), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21) 2.d Idealised Me refined as rotating group: C15(H15A,H15B,H15C) ; _shelx_res_file ; TITL 120-9_a.res in P2(1)/n 120-9.res created by SHELXL-2018/3 at 16:13:02 on 24-Apr-2023 REM Old TITL 120-9 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.153, Rweak 0.194, Alpha 0.070 REM 0.448 for 123 systematic absences, Orientation as input REM Formula found by SHELXT: C21 N2 O3 Br CELL 0.71073 9.5594 19.9216 10.3113 90 110.294 90 ZERR 4 0.0007 0.0015 0.0008 0 0.009 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Br F N O UNIT 84 68 4 8 8 4 L.S. 10 PLAN 5 TEMP -120 CONF BOND list 4 fmap 2 acta MORE -1 BOND $H OMIT -3 50 REM REM REM WGHT 0.039100 0.306400 FVAR 0.50486 BR1 3 0.351714 0.540445 0.210098 11.00000 0.03456 0.03680 = 0.04232 0.00131 0.00645 -0.01326 F1 4 0.501504 0.636216 0.566078 11.00000 0.04470 0.05980 = 0.03720 0.00634 0.02367 -0.00266 F2 4 0.718552 0.586454 0.645875 11.00000 0.06454 0.04021 = 0.02676 0.01343 0.00852 0.00840 O1 6 0.611209 0.777519 0.691518 11.00000 0.06863 0.05405 = 0.02576 -0.00569 0.01266 0.01280 N1 5 0.551356 0.748638 0.337356 11.00000 0.02495 0.02338 = 0.02357 0.00125 0.00448 0.00015 N2 5 0.622835 0.752638 0.484228 11.00000 0.02800 0.03214 = 0.01949 -0.00045 0.00258 0.00358 C1 1 0.555267 0.699103 0.080870 11.00000 0.01811 0.03546 = 0.02299 0.00655 0.00432 0.00736 C2 1 0.536880 0.679690 -0.054329 11.00000 0.02941 0.05106 = 0.02675 0.01104 0.01170 0.01176 AFIX 43 H2 2 0.573533 0.707748 -0.109879 11.00000 -1.20000 AFIX 0 C3 1 0.466512 0.620578 -0.107922 11.00000 0.03734 0.05015 = 0.02589 -0.00344 0.00693 0.01385 AFIX 43 H3 2 0.455767 0.608068 -0.199790 11.00000 -1.20000 AFIX 0 C4 1 0.411195 0.579120 -0.029690 11.00000 0.03167 0.03649 = 0.02878 -0.00695 -0.00209 0.00722 AFIX 43 H4 2 0.363004 0.538113 -0.066529 11.00000 -1.20000 AFIX 0 C5 1 0.427591 0.598697 0.103648 11.00000 0.02244 0.03042 = 0.02584 0.00254 0.00077 0.00442 C6 1 0.499531 0.657611 0.161622 11.00000 0.01208 0.02958 = 0.02339 0.00227 0.00329 0.00513 C7 1 0.522031 0.676196 0.308965 11.00000 0.01546 0.02433 = 0.02312 0.00102 0.00576 -0.00046 AFIX 13 H7 2 0.429250 0.664320 0.327816 11.00000 -1.20000 AFIX 0 C8 1 0.657561 0.640096 0.420020 11.00000 0.02127 0.02537 = 0.01862 0.00210 0.00398 -0.00087 C9 1 0.638131 0.633197 0.555478 11.00000 0.03430 0.03690 = 0.02509 0.00633 0.00848 0.00414 C10 1 0.714623 0.693887 0.534516 11.00000 0.02603 0.02699 = 0.02285 -0.00076 0.00214 0.00294 AFIX 13 H10 2 0.824197 0.699168 0.584694 11.00000 -1.20000 AFIX 0 C11 1 0.632478 0.760078 0.143134 11.00000 0.02711 0.03410 = 0.03378 0.01337 0.01150 0.00184 AFIX 43 H11 2 0.682570 0.785782 0.095016 11.00000 -1.20000 AFIX 0 C12 1 0.634333 0.780578 0.266242 11.00000 0.02066 0.02497 = 0.03705 0.00804 0.00544 -0.00091 AFIX 43 H12 2 0.693983 0.818247 0.307814 11.00000 -1.20000 AFIX 0 C13 1 0.555389 0.784119 0.566954 11.00000 0.03550 0.03358 = 0.03519 -0.00626 0.01303 -0.00010 C14 1 0.420394 0.826913 0.495423 11.00000 0.03536 0.05225 = 0.03968 -0.01154 0.01062 0.00706 AFIX 23 H14A 2 0.362750 0.833198 0.557872 11.00000 -1.20000 H14B 2 0.355616 0.803297 0.411636 11.00000 -1.20000 AFIX 0 C15 1 0.462121 0.894806 0.454633 11.00000 0.06019 0.05523 = 0.04733 0.00501 0.01009 0.02248 AFIX 137 H15A 2 0.506852 0.889149 0.382989 11.00000 -1.50000 H15B 2 0.534037 0.916558 0.535691 11.00000 -1.50000 H15C 2 0.372547 0.922757 0.418756 11.00000 -1.50000 AFIX 0 C16 1 0.762789 0.596350 0.381366 11.00000 0.02769 0.02917 = 0.01624 0.00253 -0.00019 0.00520 C17 1 0.749491 0.526850 0.378978 11.00000 0.03298 0.02966 = 0.03147 -0.00069 -0.00279 0.00203 AFIX 43 H17 2 0.671907 0.506123 0.402338 11.00000 -1.20000 AFIX 0 C18 1 0.851094 0.487605 0.341951 11.00000 0.05520 0.03146 = 0.03495 -0.00855 -0.00947 0.01439 AFIX 43 H18 2 0.841541 0.440113 0.339195 11.00000 -1.20000 AFIX 0 C19 1 0.963788 0.517005 0.309769 11.00000 0.04428 0.06684 = 0.03124 -0.00467 0.00543 0.02360 AFIX 43 H19 2 1.031859 0.489796 0.284526 11.00000 -1.20000 AFIX 0 C20 1 0.979629 0.585124 0.313503 11.00000 0.04038 0.06289 = 0.03768 0.01001 0.01883 0.01664 AFIX 43 H20 2 1.058981 0.605230 0.291917 11.00000 -1.20000 AFIX 0 C21 1 0.879478 0.624792 0.348909 11.00000 0.03649 0.03726 = 0.03221 0.00843 0.01320 0.00724 AFIX 43 H21 2 0.890605 0.672210 0.351081 11.00000 -1.20000 AFIX 0 HKLF 4 REM 120-9_a.res in P2(1)/n REM wR2 = 0.0874, GooF = S = 1.034, Restrained GooF = 1.034 for all data REM R1 = 0.0372 for 2550 Fo > 4sig(Fo) and 0.0546 for all 3249 data REM 245 parameters refined using 0 restraints END WGHT 0.0444 0.1885 REM Highest difference peak 0.624, deepest hole -0.594, 1-sigma level 0.072 Q1 1 0.2396 0.5439 0.1796 11.00000 0.05 0.62 Q2 1 0.4585 0.5383 0.2393 11.00000 0.05 0.52 Q3 1 0.5319 0.7147 0.3241 11.00000 0.05 0.28 Q4 1 0.6200 0.6264 0.4621 11.00000 0.05 0.27 Q5 1 0.3338 0.7238 0.4393 11.00000 0.05 0.25 ; _shelx_res_checksum 30807 _olex2_date_sample_data_collection 2023-04-23 _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 1.219 _oxdiff_exptl_absorpt_empirical_full_min 0.784 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 Br1 Br 0.35171(3) 0.54045(2) 0.21010(3) 0.03971(13) Uani 1 1 d . . . . . F1 F 0.5015(2) 0.63622(10) 0.56608(15) 0.0447(5) Uani 1 1 d . . . . . F2 F 0.7186(2) 0.58645(9) 0.64587(15) 0.0458(5) Uani 1 1 d . . . . . O1 O 0.6112(3) 0.77752(11) 0.6915(2) 0.0505(6) Uani 1 1 d . . . . . N1 N 0.5514(2) 0.74864(11) 0.3374(2) 0.0250(5) Uani 1 1 d . . . . . N2 N 0.6228(3) 0.75264(12) 0.4842(2) 0.0280(6) Uani 1 1 d . . . . . C1 C 0.5553(3) 0.69910(15) 0.0809(3) 0.0263(7) Uani 1 1 d . . . . . C2 C 0.5369(3) 0.67969(17) -0.0543(3) 0.0352(8) Uani 1 1 d . . . . . H2 H 0.573533 0.707748 -0.109879 0.042 Uiso 1 1 calc R U . . . C3 C 0.4665(3) 0.62058(17) -0.1079(3) 0.0389(8) Uani 1 1 d . . . . . H3 H 0.455767 0.608068 -0.199790 0.047 Uiso 1 1 calc R U . . . C4 C 0.4112(3) 0.57912(16) -0.0297(3) 0.0356(8) Uani 1 1 d . . . . . H4 H 0.363004 0.538113 -0.066529 0.043 Uiso 1 1 calc R U . . . C5 C 0.4276(3) 0.59870(15) 0.1036(3) 0.0282(7) Uani 1 1 d . . . . . C6 C 0.4995(3) 0.65761(14) 0.1616(2) 0.0224(6) Uani 1 1 d . . . . . C7 C 0.5220(3) 0.67620(14) 0.3090(2) 0.0212(6) Uani 1 1 d . . . . . H7 H 0.429250 0.664320 0.327816 0.025 Uiso 1 1 calc R U . . . C8 C 0.6576(3) 0.64010(14) 0.4200(2) 0.0225(6) Uani 1 1 d . . . . . C9 C 0.6381(3) 0.63320(16) 0.5555(3) 0.0326(7) Uani 1 1 d . . . . . C10 C 0.7146(3) 0.69389(14) 0.5345(3) 0.0270(7) Uani 1 1 d . . . . . H10 H 0.824197 0.699168 0.584694 0.032 Uiso 1 1 calc R U . . . C11 C 0.6325(3) 0.76008(15) 0.1431(3) 0.0314(7) Uani 1 1 d . . . . . H11 H 0.682570 0.785782 0.095016 0.038 Uiso 1 1 calc R U . . . C12 C 0.6343(3) 0.78058(15) 0.2662(3) 0.0288(7) Uani 1 1 d . . . . . H12 H 0.693983 0.818247 0.307814 0.035 Uiso 1 1 calc R U . . . C13 C 0.5554(3) 0.78412(16) 0.5670(3) 0.0346(7) Uani 1 1 d . . . . . C14 C 0.4204(4) 0.82691(18) 0.4954(3) 0.0431(8) Uani 1 1 d . . . . . H14A H 0.362750 0.833198 0.557872 0.052 Uiso 1 1 calc R U . . . H14B H 0.355616 0.803297 0.411636 0.052 Uiso 1 1 calc R U . . . C15 C 0.4621(4) 0.89481(19) 0.4546(3) 0.0565(10) Uani 1 1 d . . . . . H15A H 0.506852 0.889149 0.382989 0.085 Uiso 1 1 calc R U . . . H15B H 0.534037 0.916558 0.535691 0.085 Uiso 1 1 calc R U . . . H15C H 0.372547 0.922757 0.418756 0.085 Uiso 1 1 calc R U . . . C16 C 0.7628(3) 0.59635(15) 0.3814(2) 0.0264(7) Uani 1 1 d . . . . . C17 C 0.7495(4) 0.52685(15) 0.3790(3) 0.0350(8) Uani 1 1 d . . . . . H17 H 0.671907 0.506123 0.402338 0.042 Uiso 1 1 calc R U . . . C18 C 0.8511(4) 0.48761(18) 0.3420(3) 0.0471(9) Uani 1 1 d . . . . . H18 H 0.841541 0.440113 0.339195 0.057 Uiso 1 1 calc R U . . . C19 C 0.9638(4) 0.5170(2) 0.3098(3) 0.0495(10) Uani 1 1 d . . . . . H19 H 1.031859 0.489796 0.284526 0.059 Uiso 1 1 calc R U . . . C20 C 0.9796(4) 0.5851(2) 0.3135(3) 0.0456(9) Uani 1 1 d . . . . . H20 H 1.058981 0.605230 0.291917 0.055 Uiso 1 1 calc R U . . . C21 C 0.8795(3) 0.62479(17) 0.3489(3) 0.0350(7) Uani 1 1 d . . . . . H21 H 0.890605 0.672210 0.351081 0.042 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 0.0346(2) 0.0368(2) 0.0423(2) 0.00131(14) 0.00645(14) -0.01326(15) F1 0.0447(11) 0.0598(13) 0.0372(10) 0.0063(8) 0.0237(8) -0.0027(10) F2 0.0645(13) 0.0402(12) 0.0268(9) 0.0134(8) 0.0085(8) 0.0084(10) O1 0.0686(17) 0.0541(16) 0.0258(13) -0.0057(10) 0.0127(11) 0.0128(14) N1 0.0250(13) 0.0234(14) 0.0236(12) 0.0013(9) 0.0045(9) 0.0001(11) N2 0.0280(13) 0.0321(15) 0.0195(12) -0.0004(10) 0.0026(10) 0.0036(12) C1 0.0181(15) 0.0355(19) 0.0230(15) 0.0065(12) 0.0043(11) 0.0074(13) C2 0.0294(17) 0.051(2) 0.0268(16) 0.0110(14) 0.0117(13) 0.0118(16) C3 0.0373(19) 0.050(2) 0.0259(16) -0.0034(15) 0.0069(13) 0.0139(18) C4 0.0317(18) 0.036(2) 0.0288(17) -0.0069(14) -0.0021(13) 0.0072(16) C5 0.0224(15) 0.0304(18) 0.0258(15) 0.0025(12) 0.0008(11) 0.0044(14) C6 0.0121(13) 0.0296(18) 0.0234(14) 0.0023(12) 0.0033(11) 0.0051(13) C7 0.0155(14) 0.0243(16) 0.0231(14) 0.0010(11) 0.0058(11) -0.0005(12) C8 0.0213(15) 0.0254(16) 0.0186(13) 0.0021(11) 0.0040(11) -0.0009(13) C9 0.0343(18) 0.037(2) 0.0251(15) 0.0063(13) 0.0085(13) 0.0041(15) C10 0.0260(16) 0.0270(17) 0.0229(14) -0.0008(12) 0.0021(11) 0.0029(14) C11 0.0271(16) 0.0341(19) 0.0338(17) 0.0134(13) 0.0115(13) 0.0018(15) C12 0.0207(15) 0.0250(17) 0.0370(17) 0.0080(13) 0.0054(12) -0.0009(13) C13 0.0355(18) 0.0336(19) 0.0352(19) -0.0063(13) 0.0130(14) -0.0001(15) C14 0.0354(19) 0.052(2) 0.0397(18) -0.0115(16) 0.0106(14) 0.0071(17) C15 0.060(3) 0.055(3) 0.047(2) 0.0050(17) 0.0101(17) 0.022(2) C16 0.0277(16) 0.0292(18) 0.0162(13) 0.0025(11) -0.0002(11) 0.0052(14) C17 0.0330(18) 0.030(2) 0.0315(17) -0.0007(13) -0.0028(13) 0.0020(15) C18 0.055(2) 0.031(2) 0.0350(18) -0.0085(14) -0.0095(16) 0.0144(19) C19 0.044(2) 0.067(3) 0.0312(18) -0.0047(17) 0.0054(15) 0.024(2) C20 0.040(2) 0.063(3) 0.0377(18) 0.0100(16) 0.0188(15) 0.017(2) C21 0.0365(18) 0.037(2) 0.0322(16) 0.0084(13) 0.0132(13) 0.0072(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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' 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 N2 N1 C7 104.58(19) . . ? C12 N1 N2 112.2(2) . . ? C12 N1 C7 116.2(2) . . ? N1 N2 C10 110.0(2) . . ? C13 N2 N1 121.6(2) . . ? C13 N2 C10 120.0(2) . . ? C2 C1 C6 119.1(3) . . ? C2 C1 C11 122.8(3) . . ? C6 C1 C11 118.1(2) . . ? C1 C2 H2 119.6 . . ? C3 C2 C1 120.9(3) . . ? C3 C2 H2 119.6 . . ? C2 C3 H3 119.6 . . ? C2 C3 C4 120.7(3) . . ? C4 C3 H3 119.6 . . ? C3 C4 H4 120.8 . . ? C3 C4 C5 118.5(3) . . ? C5 C4 H4 120.8 . . ? C4 C5 Br1 117.8(2) . . ? C4 C5 C6 122.3(3) . . ? C6 C5 Br1 119.88(19) . . ? C1 C6 C7 120.2(2) . . ? C5 C6 C1 118.5(2) . . ? C5 C6 C7 121.3(2) . . ? N1 C7 C6 113.0(2) . . ? N1 C7 H7 108.2 . . ? N1 C7 C8 104.5(2) . . ? C6 C7 H7 108.2 . . ? C6 C7 C8 114.5(2) . . ? C8 C7 H7 108.2 . . ? C9 C8 C7 112.9(2) . . ? C9 C8 C10 57.98(18) . . ? C9 C8 C16 121.2(2) . . ? C10 C8 C7 102.8(2) . . ? C16 C8 C7 122.4(2) . . ? C16 C8 C10 121.2(2) . . ? F1 C9 F2 108.0(2) . . ? F1 C9 C8 121.0(2) . . ? F1 C9 C10 121.4(3) . . ? F2 C9 C8 119.2(3) . . ? F2 C9 C10 118.4(2) . . ? C10 C9 C8 63.37(19) . . ? N2 C10 C8 106.1(2) . . ? N2 C10 C9 116.6(2) . . ? N2 C10 H10 119.8 . . ? C8 C10 H10 119.8 . . ? C9 C10 C8 58.65(18) . . ? C9 C10 H10 119.8 . . ? C1 C11 H11 119.4 . . ? C12 C11 C1 121.1(3) . . ? C12 C11 H11 119.4 . . ? N1 C12 H12 118.8 . . ? C11 C12 N1 122.5(3) . . ? C11 C12 H12 118.8 . . ? O1 C13 N2 118.3(3) . . ? O1 C13 C14 124.4(3) . . ? N2 C13 C14 117.2(2) . . ? C13 C14 H14A 109.2 . . ? C13 C14 H14B 109.2 . . ? C13 C14 C15 112.2(3) . . ? H14A C14 H14B 107.9 . . ? C15 C14 H14A 109.2 . . ? C15 C14 H14B 109.2 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C8 121.5(3) . . ? C17 C16 C21 118.5(3) . . ? C21 C16 C8 120.0(3) . . ? C16 C17 H17 120.2 . . ? C16 C17 C18 119.6(3) . . ? C18 C17 H17 120.2 . . ? C17 C18 H18 119.7 . . ? C19 C18 C17 120.5(3) . . ? C19 C18 H18 119.7 . . ? C18 C19 H19 119.7 . . ? C20 C19 C18 120.6(3) . . ? C20 C19 H19 119.7 . . ? C19 C20 H20 120.2 . . ? C19 C20 C21 119.7(3) . . ? C21 C20 H20 120.2 . . ? C16 C21 H21 119.5 . . ? C20 C21 C16 121.1(3) . . ? C20 C21 H21 119.5 . . ? 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 C5 1.905(3) . ? F1 C9 1.349(3) . ? F2 C9 1.353(3) . ? O1 C13 1.215(3) . ? N1 N2 1.431(3) . ? N1 C7 1.480(3) . ? N1 C12 1.405(3) . ? N2 C10 1.447(4) . ? N2 C13 1.385(4) . ? C1 C2 1.398(4) . ? C1 C6 1.403(4) . ? C1 C11 1.450(4) . ? C2 H2 0.9500 . ? C2 C3 1.374(5) . ? C3 H3 0.9500 . ? C3 C4 1.381(4) . ? C4 H4 0.9500 . ? C4 C5 1.385(4) . ? C5 C6 1.387(4) . ? C6 C7 1.505(3) . ? C7 H7 1.0000 . ? C7 C8 1.574(4) . ? C8 C9 1.478(4) . ? C8 C10 1.547(4) . ? C8 C16 1.486(4) . ? C9 C10 1.467(4) . ? C10 H10 1.0000 . ? C11 H11 0.9500 . ? C11 C12 1.328(4) . ? C12 H12 0.9500 . ? C13 C14 1.509(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C14 C15 1.511(5) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.390(4) . ? C16 C21 1.392(4) . ? C17 H17 0.9500 . ? C17 C18 1.399(5) . ? C18 H18 0.9500 . ? C18 C19 1.364(5) . ? C19 H19 0.9500 . ? C19 C20 1.365(5) . ? C20 H20 0.9500 . ? C20 C21 1.384(4) . ? C21 H21 0.9500 . ? 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 Br1 C5 C6 C1 179.44(19) . . . . ? Br1 C5 C6 C7 1.2(4) . . . . ? F1 C9 C10 N2 -18.3(3) . . . . ? F1 C9 C10 C8 -111.6(3) . . . . ? F2 C9 C10 N2 -156.3(2) . . . . ? F2 C9 C10 C8 110.4(3) . . . . ? O1 C13 C14 C15 98.7(4) . . . . ? N1 N2 C10 C8 -19.1(3) . . . . ? N1 N2 C10 C9 -81.6(3) . . . . ? N1 N2 C13 O1 169.5(3) . . . . ? N1 N2 C13 C14 -13.0(4) . . . . ? N1 C7 C8 C9 82.5(3) . . . . ? N1 C7 C8 C10 22.1(2) . . . . ? N1 C7 C8 C16 -118.6(3) . . . . ? N2 N1 C7 C6 -159.1(2) . . . . ? N2 N1 C7 C8 -33.9(2) . . . . ? N2 N1 C12 C11 148.9(3) . . . . ? N2 C13 C14 C15 -78.6(3) . . . . ? C1 C2 C3 C4 0.5(5) . . . . ? C1 C6 C7 N1 21.8(3) . . . . ? C1 C6 C7 C8 -97.7(3) . . . . ? C1 C11 C12 N1 -6.1(4) . . . . ? C2 C1 C6 C5 -0.2(4) . . . . ? C2 C1 C6 C7 178.1(2) . . . . ? C2 C1 C11 C12 172.8(3) . . . . ? C2 C3 C4 C5 0.3(5) . . . . ? C3 C4 C5 Br1 -179.6(2) . . . . ? C3 C4 C5 C6 -1.1(4) . . . . ? C4 C5 C6 C1 1.0(4) . . . . ? C4 C5 C6 C7 -177.2(2) . . . . ? C5 C6 C7 N1 -160.0(2) . . . . ? C5 C6 C7 C8 80.5(3) . . . . ? C6 C1 C2 C3 -0.6(4) . . . . ? C6 C1 C11 C12 -8.4(4) . . . . ? C6 C7 C8 C9 -153.3(2) . . . . ? C6 C7 C8 C10 146.3(2) . . . . ? C6 C7 C8 C16 5.5(4) . . . . ? C7 N1 N2 C10 34.0(3) . . . . ? C7 N1 N2 C13 -114.0(3) . . . . ? C7 N1 C12 C11 28.7(4) . . . . ? C7 C8 C9 F1 21.1(4) . . . . ? C7 C8 C9 F2 159.6(2) . . . . ? C7 C8 C9 C10 -91.2(2) . . . . ? C7 C8 C10 N2 -2.6(3) . . . . ? C7 C8 C10 C9 109.1(2) . . . . ? C7 C8 C16 C17 -99.2(3) . . . . ? C7 C8 C16 C21 82.0(3) . . . . ? C8 C9 C10 N2 93.3(2) . . . . ? C8 C16 C17 C18 180.0(2) . . . . ? C8 C16 C21 C20 179.6(2) . . . . ? C9 C8 C10 N2 -111.7(3) . . . . ? C9 C8 C16 C17 57.9(4) . . . . ? C9 C8 C16 C21 -120.9(3) . . . . ? C10 N2 C13 O1 24.7(4) . . . . ? C10 N2 C13 C14 -157.9(3) . . . . ? C10 C8 C9 F1 112.3(3) . . . . ? C10 C8 C9 F2 -109.2(3) . . . . ? C10 C8 C16 C17 127.0(3) . . . . ? C10 C8 C16 C21 -51.9(3) . . . . ? C11 C1 C2 C3 178.2(3) . . . . ? C11 C1 C6 C5 -179.0(2) . . . . ? C11 C1 C6 C7 -0.8(4) . . . . ? C12 N1 N2 C10 -92.8(3) . . . . ? C12 N1 N2 C13 119.3(3) . . . . ? C12 N1 C7 C6 -34.8(3) . . . . ? C12 N1 C7 C8 90.3(2) . . . . ? C13 N2 C10 C8 129.5(3) . . . . ? C13 N2 C10 C9 66.9(3) . . . . ? C16 C8 C9 F1 -138.1(3) . . . . ? C16 C8 C9 F2 0.4(4) . . . . ? C16 C8 C9 C10 109.7(3) . . . . ? C16 C8 C10 N2 138.7(2) . . . . ? C16 C8 C10 C9 -109.6(3) . . . . ? C16 C17 C18 C19 0.7(4) . . . . ? C17 C16 C21 C20 0.7(4) . . . . ? C17 C18 C19 C20 0.2(5) . . . . ? C18 C19 C20 C21 -0.7(4) . . . . ? C19 C20 C21 C16 0.2(4) . . . . ? C21 C16 C17 C18 -1.1(4) . . . . ?