#------------------------------------------------------------------------------ #$Date: 2023-11-16 04:16:09 +0200 (Thu, 16 Nov 2023) $ #$Revision: 287637 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247744.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_7247744 loop_ _publ_author_name 'Yang, Ruchun' 'Xiong, Yongge' 'Deng, Si' 'Bai, Jiang' 'Song, Xian-Rong' 'Xiao, Qiang' _publ_section_title ; NBS-mediated bromination and dehydrogenation of tetrahydro-quinoline in one pot: scope and mechanistic study ; _journal_issue 47 _journal_name_full 'RSC Advances' _journal_page_first 33495 _journal_page_last 33499 _journal_paper_doi 10.1039/D3RA06747E _journal_volume 13 _journal_year 2023 _chemical_formula_sum 'C24 H16 Br N' _chemical_formula_weight 398.29 _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 _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2023-09-16 deposited with the CCDC. 2023-11-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.655(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.3380(14) _cell_length_b 12.4628(15) _cell_length_c 13.4549(17) _cell_measurement_reflns_used 2768 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 25.91 _cell_measurement_theta_min 2.49 _cell_volume 1821.5(4) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0251 _diffrn_reflns_av_unetI/netI 0.0299 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9087 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.000 _diffrn_reflns_theta_min 2.643 _exptl_absorpt_coefficient_mu 2.263 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.452 _exptl_crystal_description block _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.240 _refine_diff_density_max 0.290 _refine_diff_density_min -0.497 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.990 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3192 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.990 _refine_ls_R_factor_all 0.0567 _refine_ls_R_factor_gt 0.0344 _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^)+(0.0537P)^2^+0.3415P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0860 _refine_ls_wR_factor_ref 0.0932 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2334 _reflns_number_total 3192 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra06747e2.cif _cod_data_source_block 1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7247744 _shelx_shelxl_version_number 2014/7 _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_min 0.591 _shelx_estimated_absorpt_t_max 0.613 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1_a.res in P2(1)/n CELL 0.71073 11.338 12.4628 13.4549 90 106.655 90 ZERR 4 0.0014 0.0015 0.0017 0 0.002 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N Br UNIT 96 64 4 4 omit 1 1 0 omit 0 2 1 omit 2 0 2 OMIT 0.00 50.00 L.S. 24 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 size 0.26 0.25 0.24 conf htab TEMP 23 WGHT 0.053700 0.341500 FVAR 0.35691 BR1 4 0.557189 0.264802 -0.192374 11.00000 0.07943 0.09887 = 0.03097 -0.01669 0.00798 -0.00724 N1 3 0.381779 0.377464 0.010551 11.00000 0.03732 0.05724 = 0.03951 -0.00052 -0.00503 0.00123 C11 1 0.597678 0.363548 0.112253 11.00000 0.03355 0.03462 = 0.02919 0.00066 0.00231 -0.00156 C10 1 0.685328 0.372002 0.211270 11.00000 0.03122 0.04362 = 0.03031 0.00010 0.00358 -0.00073 AFIX 43 H10 2 0.767813 0.357303 0.218634 11.00000 -1.20000 AFIX 0 C12 1 0.472374 0.386326 0.102814 11.00000 0.03556 0.03523 = 0.03717 0.00244 0.00128 -0.00104 C7 1 0.800181 0.400934 0.484991 11.00000 0.04278 0.04424 = 0.03296 -0.00157 0.00806 0.00024 C6 1 0.882142 0.394214 0.588927 11.00000 0.04358 0.03963 = 0.02932 -0.00451 0.00269 0.00359 C9 1 0.648868 0.401826 0.296381 11.00000 0.03781 0.03968 = 0.03085 -0.00038 0.00335 -0.00358 C16 1 0.630113 0.326504 0.022875 11.00000 0.04217 0.03550 = 0.02985 0.00105 0.00491 -0.00067 C8 1 0.733961 0.403696 0.398457 11.00000 0.04020 0.04511 = 0.03231 -0.00193 0.01037 -0.00022 C5 1 1.007526 0.406617 0.607744 11.00000 0.04742 0.05394 = 0.04194 0.00769 0.00756 0.00030 AFIX 43 H5 2 1.039840 0.422095 0.553167 11.00000 -1.20000 AFIX 0 C17 1 0.534919 0.315519 -0.066390 11.00000 0.05179 0.04875 = 0.02768 -0.00431 0.00276 -0.00391 C13 1 0.436346 0.417875 0.191428 11.00000 0.03604 0.04413 = 0.04193 -0.00011 0.00670 0.00258 C20 1 0.847704 0.383050 0.049635 11.00000 0.04351 0.05790 = 0.03227 0.00246 0.00439 0.00015 AFIX 43 H20 2 0.824633 0.452637 0.060674 11.00000 -1.20000 AFIX 0 C18 1 0.414291 0.342828 -0.068891 11.00000 0.04754 0.05975 = 0.03330 -0.00345 -0.01011 -0.00388 AFIX 43 H18 2 0.353270 0.335703 -0.131661 11.00000 -1.20000 AFIX 0 C19 1 0.760704 0.302011 0.029090 11.00000 0.04505 0.05261 = 0.02296 -0.00159 0.00866 0.00343 C14 1 0.524204 0.425640 0.284637 11.00000 0.04403 0.05017 = 0.03456 -0.00125 0.01176 0.00360 AFIX 43 H14 2 0.501015 0.447409 0.342444 11.00000 -1.20000 AFIX 0 C1 1 0.836354 0.370200 0.671904 11.00000 0.04693 0.07199 = 0.03346 -0.00415 0.00839 -0.00317 AFIX 43 H1 2 0.752073 0.361622 0.660755 11.00000 -1.20000 AFIX 0 C4 1 1.085258 0.396212 0.706964 11.00000 0.04188 0.05726 = 0.05661 0.00576 -0.00542 -0.00249 AFIX 43 H4 2 1.169500 0.405975 0.718918 11.00000 -1.20000 AFIX 0 C3 1 1.039637 0.371626 0.788153 11.00000 0.06594 0.05878 = 0.03289 -0.00018 -0.00824 0.00408 AFIX 43 H3 2 1.092703 0.363537 0.854691 11.00000 -1.20000 AFIX 0 C2 1 0.915358 0.359062 0.770580 11.00000 0.07125 0.07764 = 0.03056 0.00102 0.00938 0.00402 AFIX 43 H2 2 0.883998 0.342906 0.825557 11.00000 -1.20000 AFIX 0 C21 1 0.968742 0.361475 0.053902 11.00000 0.04096 0.08999 = 0.04284 0.01451 0.00642 0.00122 AFIX 43 H21 2 1.026647 0.416442 0.067914 11.00000 -1.20000 AFIX 0 C24 1 0.796776 0.198285 0.014759 11.00000 0.07289 0.05552 = 0.04465 -0.00119 0.02357 0.00768 AFIX 43 H24 2 0.739718 0.142671 0.002382 11.00000 -1.20000 AFIX 0 C22 1 1.003183 0.259828 0.037605 11.00000 0.05287 0.11638 = 0.04228 0.02837 0.01907 0.03272 AFIX 43 H22 2 1.084257 0.245910 0.039095 11.00000 -1.20000 AFIX 0 C15 1 0.301770 0.437294 0.181357 11.00000 0.04199 0.08633 = 0.06344 -0.00097 0.01594 0.01222 AFIX 137 H15A 2 0.274736 0.500906 0.141025 11.00000 -1.50000 H15B 2 0.290987 0.446277 0.249079 11.00000 -1.50000 H15C 2 0.254150 0.377027 0.147573 11.00000 -1.50000 AFIX 0 C23 1 0.918788 0.177714 0.018970 11.00000 0.08967 0.07648 = 0.04637 0.01415 0.02970 0.03894 AFIX 43 H23 2 0.943239 0.108244 0.009151 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1_a.res in P2(1)/n REM R1 = 0.0344 for 2334 Fo > 4sig(Fo) and 0.0567 for all 3192 data REM 236 parameters refined using 0 restraints END WGHT 0.0399 0.4831 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.290, deepest hole -0.497, 1-sigma level 0.049 Q1 1 0.5759 0.1989 -0.1556 11.00000 0.05 0.29 Q2 1 0.6407 0.3796 0.1524 11.00000 0.05 0.19 Q3 1 0.6278 0.3032 -0.1795 11.00000 0.05 0.19 Q4 1 0.7232 0.0988 0.0466 11.00000 0.05 0.17 Q5 1 0.3183 0.3067 -0.1272 11.00000 0.05 0.17 Q6 1 0.6823 0.3659 0.3510 11.00000 0.05 0.17 Q7 1 0.6182 0.3596 0.0660 11.00000 0.05 0.16 Q8 1 0.5274 0.3394 0.1115 11.00000 0.05 0.16 Q9 1 0.8802 0.2820 0.8334 11.00000 0.05 0.16 Q10 1 0.6683 0.4301 0.2670 11.00000 0.05 0.15 Q11 1 0.7832 0.3367 0.0503 11.00000 0.05 0.15 Q12 1 0.7025 0.3180 0.0255 11.00000 0.05 0.15 Q13 1 0.4567 0.3803 0.1465 11.00000 0.05 0.14 Q14 1 0.5581 0.3839 -0.1837 11.00000 0.05 0.14 Q15 1 1.0635 0.2751 0.0329 11.00000 0.05 0.14 Q16 1 1.1552 0.5209 0.7480 11.00000 0.05 0.14 Q17 1 0.7991 0.3840 0.4198 11.00000 0.05 0.14 Q18 1 0.5372 0.4115 0.1060 11.00000 0.05 0.13 Q19 1 1.1889 0.3760 0.6817 11.00000 0.05 0.13 Q20 1 0.5997 0.3762 0.0000 11.00000 0.05 0.13 ; _shelx_res_checksum 9379 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 0.55719(3) 0.26480(3) -0.19237(2) 0.07139(16) Uani 1 1 d . . . . . N1 N 0.38178(18) 0.37746(18) 0.01055(16) 0.0480(6) Uani 1 1 d . . . . . C11 C 0.5977(2) 0.36355(18) 0.11225(17) 0.0338(5) Uani 1 1 d . . . . . C10 C 0.6853(2) 0.37200(19) 0.21127(17) 0.0361(5) Uani 1 1 d . . . . . H10 H 0.7678 0.3573 0.2186 0.043 Uiso 1 1 calc R U . . . C12 C 0.4724(2) 0.38633(19) 0.10281(18) 0.0379(6) Uani 1 1 d . . . . . C7 C 0.8002(2) 0.4009(2) 0.48499(18) 0.0406(6) Uani 1 1 d . . . . . C6 C 0.8821(2) 0.39421(19) 0.58893(18) 0.0391(6) Uani 1 1 d . . . . . C9 C 0.6489(2) 0.40183(19) 0.29638(18) 0.0375(6) Uani 1 1 d . . . . . C16 C 0.6301(2) 0.32650(19) 0.02287(17) 0.0370(6) Uani 1 1 d . . . . . C8 C 0.7340(2) 0.40370(19) 0.39846(18) 0.0392(6) Uani 1 1 d . . . . . C5 C 1.0075(2) 0.4066(2) 0.6077(2) 0.0489(7) Uani 1 1 d . . . . . H5 H 1.0398 0.4221 0.5532 0.059 Uiso 1 1 calc R U . . . C17 C 0.5349(2) 0.3155(2) -0.06639(17) 0.0445(6) Uani 1 1 d . . . . . C13 C 0.4363(2) 0.4179(2) 0.19143(19) 0.0416(6) Uani 1 1 d . . . . . C20 C 0.8477(2) 0.3830(2) 0.04963(18) 0.0459(6) Uani 1 1 d . . . . . H20 H 0.8246 0.4526 0.0607 0.055 Uiso 1 1 calc R U . . . C18 C 0.4143(2) 0.3428(2) -0.0689(2) 0.0514(7) Uani 1 1 d . . . . . H18 H 0.3533 0.3357 -0.1317 0.062 Uiso 1 1 calc R U . . . C19 C 0.7607(2) 0.3020(2) 0.02909(17) 0.0404(6) Uani 1 1 d . . . . . C14 C 0.5242(2) 0.4256(2) 0.28464(19) 0.0428(6) Uani 1 1 d . . . . . H14 H 0.5010 0.4474 0.3424 0.051 Uiso 1 1 calc R U . . . C1 C 0.8364(3) 0.3702(2) 0.6719(2) 0.0514(7) Uani 1 1 d . . . . . H1 H 0.7521 0.3616 0.6608 0.062 Uiso 1 1 calc R U . . . C4 C 1.0853(3) 0.3962(2) 0.7070(2) 0.0560(8) Uani 1 1 d . . . . . H4 H 1.1695 0.4060 0.7189 0.067 Uiso 1 1 calc R U . . . C3 C 1.0396(3) 0.3716(2) 0.7882(2) 0.0572(8) Uani 1 1 d . . . . . H3 H 1.0927 0.3635 0.8547 0.069 Uiso 1 1 calc R U . . . C2 C 0.9154(3) 0.3591(3) 0.7706(2) 0.0609(8) Uani 1 1 d . . . . . H2 H 0.8840 0.3429 0.8256 0.073 Uiso 1 1 calc R U . . . C21 C 0.9687(2) 0.3615(3) 0.0539(2) 0.0591(8) Uani 1 1 d . . . . . H21 H 1.0266 0.4164 0.0679 0.071 Uiso 1 1 calc R U . . . C24 C 0.7968(3) 0.1983(3) 0.0148(2) 0.0563(7) Uani 1 1 d . . . . . H24 H 0.7397 0.1427 0.0024 0.068 Uiso 1 1 calc R U . . . C22 C 1.0032(3) 0.2598(3) 0.0376(2) 0.0694(10) Uani 1 1 d . . . . . H22 H 1.0843 0.2459 0.0391 0.083 Uiso 1 1 calc R U . . . C15 C 0.3018(2) 0.4373(3) 0.1814(2) 0.0637(8) Uani 1 1 d . . . . . H15A H 0.2747 0.5009 0.1410 0.096 Uiso 1 1 calc R U . . . H15B H 0.2910 0.4463 0.2491 0.096 Uiso 1 1 calc R U . . . H15C H 0.2541 0.3770 0.1476 0.096 Uiso 1 1 calc R U . . . C23 C 0.9188(3) 0.1777(3) 0.0190(2) 0.0687(10) Uani 1 1 d . . . . . H23 H 0.9432 0.1082 0.0092 0.082 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 0.0794(3) 0.0989(3) 0.03097(18) -0.01669(14) 0.00798(15) -0.00724(18) N1 0.0373(12) 0.0572(15) 0.0395(13) -0.0005(10) -0.0050(10) 0.0012(10) C11 0.0336(13) 0.0346(13) 0.0292(12) 0.0007(10) 0.0023(10) -0.0016(10) C10 0.0312(13) 0.0436(14) 0.0303(12) 0.0001(10) 0.0036(10) -0.0007(11) C12 0.0356(14) 0.0352(14) 0.0372(14) 0.0024(10) 0.0013(11) -0.0010(10) C7 0.0428(15) 0.0442(16) 0.0330(14) -0.0016(10) 0.0081(12) 0.0002(11) C6 0.0436(15) 0.0396(15) 0.0293(13) -0.0045(10) 0.0027(11) 0.0036(11) C9 0.0378(14) 0.0397(15) 0.0308(13) -0.0004(10) 0.0033(11) -0.0036(11) C16 0.0422(14) 0.0355(14) 0.0298(12) 0.0011(10) 0.0049(10) -0.0007(11) C8 0.0402(14) 0.0451(16) 0.0323(14) -0.0019(10) 0.0104(11) -0.0002(11) C5 0.0474(17) 0.0539(18) 0.0419(15) 0.0077(12) 0.0076(13) 0.0003(13) C17 0.0518(16) 0.0487(16) 0.0277(13) -0.0043(11) 0.0028(11) -0.0039(13) C13 0.0360(14) 0.0441(15) 0.0419(15) -0.0001(11) 0.0067(12) 0.0026(11) C20 0.0435(15) 0.0579(18) 0.0323(13) 0.0025(11) 0.0044(11) 0.0001(13) C18 0.0475(17) 0.0598(19) 0.0333(14) -0.0035(12) -0.0101(12) -0.0039(13) C19 0.0451(15) 0.0526(16) 0.0230(12) -0.0016(11) 0.0087(11) 0.0034(13) C14 0.0440(15) 0.0502(16) 0.0346(14) -0.0013(11) 0.0118(11) 0.0036(12) C1 0.0469(16) 0.072(2) 0.0335(14) -0.0042(13) 0.0084(12) -0.0032(14) C4 0.0419(16) 0.0573(19) 0.0566(19) 0.0058(14) -0.0054(14) -0.0025(13) C3 0.066(2) 0.0588(19) 0.0329(15) -0.0002(12) -0.0082(14) 0.0041(15) C2 0.071(2) 0.078(2) 0.0306(14) 0.0010(13) 0.0094(14) 0.0040(17) C21 0.0410(17) 0.090(3) 0.0428(16) 0.0145(15) 0.0064(13) 0.0012(16) C24 0.073(2) 0.0555(19) 0.0446(17) -0.0012(14) 0.0236(14) 0.0077(16) C22 0.0529(18) 0.116(3) 0.0423(18) 0.0284(17) 0.0191(15) 0.033(2) C15 0.0420(16) 0.086(2) 0.063(2) -0.0010(16) 0.0159(14) 0.0122(15) C23 0.090(3) 0.076(2) 0.0464(18) 0.0141(16) 0.0297(17) 0.039(2) 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' N N 0.0061 0.0033 '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' 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 C18 N1 C12 117.1(2) . . ? C10 C11 C12 118.9(2) . . ? C10 C11 C16 122.2(2) . . ? C12 C11 C16 118.8(2) . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? N1 C12 C13 117.5(2) . . ? N1 C12 C11 122.5(2) . . ? C13 C12 C11 120.1(2) . . ? C8 C7 C6 178.0(3) . . ? C5 C6 C1 118.6(2) . . ? C5 C6 C7 121.0(2) . . ? C1 C6 C7 120.3(2) . . ? C10 C9 C14 119.7(2) . . ? C10 C9 C8 121.4(2) . . ? C14 C9 C8 118.8(2) . . ? C17 C16 C11 116.1(2) . . ? C17 C16 C19 123.2(2) . . ? C11 C16 C19 120.6(2) . . ? C7 C8 C9 176.1(3) . . ? C6 C5 C4 120.4(3) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C16 C17 C18 121.0(2) . . ? C16 C17 Br1 122.9(2) . . ? C18 C17 Br1 116.09(18) . . ? C14 C13 C12 118.8(2) . . ? C14 C13 C15 121.6(2) . . ? C12 C13 C15 119.6(2) . . ? C19 C20 C21 120.6(3) . . ? C19 C20 H20 119.7 . . ? C21 C20 H20 119.7 . . ? N1 C18 C17 124.5(2) . . ? N1 C18 H18 117.8 . . ? C17 C18 H18 117.8 . . ? C20 C19 C24 119.1(2) . . ? C20 C19 C16 120.1(2) . . ? C24 C19 C16 120.7(2) . . ? C13 C14 C9 122.2(2) . . ? C13 C14 H14 118.9 . . ? C9 C14 H14 118.9 . . ? C2 C1 C6 120.3(3) . . ? C2 C1 H1 119.8 . . ? C6 C1 H1 119.8 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C2 C3 C4 119.5(2) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C3 C2 C1 120.5(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C22 C21 C20 120.1(3) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C19 C24 C23 119.7(3) . . ? C19 C24 H24 120.1 . . ? C23 C24 H24 120.1 . . ? C21 C22 C23 120.4(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C22 C23 C24 120.1(3) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? 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 C17 1.893(2) . ? N1 C18 1.300(3) . ? N1 C12 1.370(3) . ? C11 C10 1.419(3) . ? C11 C12 1.418(3) . ? C11 C16 1.431(3) . ? C10 C9 1.375(3) . ? C10 H10 0.9300 . ? C12 C13 1.422(3) . ? C7 C8 1.191(3) . ? C7 C6 1.443(3) . ? C6 C5 1.379(3) . ? C6 C1 1.392(3) . ? C9 C14 1.408(3) . ? C9 C8 1.435(3) . ? C16 C17 1.372(3) . ? C16 C19 1.490(3) . ? C5 C4 1.379(4) . ? C5 H5 0.9300 . ? C17 C18 1.400(4) . ? C13 C14 1.363(3) . ? C13 C15 1.512(3) . ? C20 C19 1.383(4) . ? C20 C21 1.383(4) . ? C20 H20 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.386(4) . ? C14 H14 0.9300 . ? C1 C2 1.379(4) . ? C1 H1 0.9300 . ? C4 C3 1.371(4) . ? C4 H4 0.9300 . ? C3 C2 1.369(4) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C21 C22 1.362(4) . ? C21 H21 0.9300 . ? C24 C23 1.392(4) . ? C24 H24 0.9300 . ? C22 C23 1.374(5) . ? C22 H22 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C23 H23 0.9300 . ? 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 C12 C11 C10 C9 0.0(3) . . . . ? C16 C11 C10 C9 -176.1(2) . . . . ? C18 N1 C12 C13 -176.3(2) . . . . ? C18 N1 C12 C11 2.6(4) . . . . ? C10 C11 C12 N1 -178.3(2) . . . . ? C16 C11 C12 N1 -2.1(3) . . . . ? C10 C11 C12 C13 0.5(3) . . . . ? C16 C11 C12 C13 176.7(2) . . . . ? C11 C10 C9 C14 -1.0(3) . . . . ? C11 C10 C9 C8 175.6(2) . . . . ? C10 C11 C16 C17 175.8(2) . . . . ? C12 C11 C16 C17 -0.2(3) . . . . ? C10 C11 C16 C19 -4.2(3) . . . . ? C12 C11 C16 C19 179.8(2) . . . . ? C1 C6 C5 C4 -0.5(4) . . . . ? C7 C6 C5 C4 -177.7(2) . . . . ? C11 C16 C17 C18 2.0(4) . . . . ? C19 C16 C17 C18 -178.0(2) . . . . ? C11 C16 C17 Br1 -178.61(18) . . . . ? C19 C16 C17 Br1 1.4(4) . . . . ? N1 C12 C13 C14 178.9(2) . . . . ? C11 C12 C13 C14 0.0(4) . . . . ? N1 C12 C13 C15 1.5(4) . . . . ? C11 C12 C13 C15 -177.4(2) . . . . ? C12 N1 C18 C17 -0.8(4) . . . . ? C16 C17 C18 N1 -1.6(4) . . . . ? Br1 C17 C18 N1 179.0(2) . . . . ? C21 C20 C19 C24 1.2(3) . . . . ? C21 C20 C19 C16 -178.9(2) . . . . ? C17 C16 C19 C20 115.3(3) . . . . ? C11 C16 C19 C20 -64.6(3) . . . . ? C17 C16 C19 C24 -64.8(3) . . . . ? C11 C16 C19 C24 115.2(3) . . . . ? C12 C13 C14 C9 -1.1(4) . . . . ? C15 C13 C14 C9 176.3(2) . . . . ? C10 C9 C14 C13 1.6(4) . . . . ? C8 C9 C14 C13 -175.1(2) . . . . ? C5 C6 C1 C2 -0.1(4) . . . . ? C7 C6 C1 C2 177.1(3) . . . . ? C6 C5 C4 C3 1.1(4) . . . . ? C5 C4 C3 C2 -1.1(4) . . . . ? C4 C3 C2 C1 0.5(5) . . . . ? C6 C1 C2 C3 0.1(5) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? C20 C19 C24 C23 -1.4(4) . . . . ? C16 C19 C24 C23 178.8(2) . . . . ? C20 C21 C22 C23 -1.3(4) . . . . ? C21 C22 C23 C24 1.2(4) . . . . ? C19 C24 C23 C22 0.2(4) . . . . ?