#------------------------------------------------------------------------------ #$Date: 2016-01-01 06:43:13 +0200 (Fri, 01 Jan 2016) $ #$Revision: 171830 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/07/1540739.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_1540739 loop_ _publ_author_name 'Mazaheripour, Amir' 'Dibble, David J.' 'Umerani, Mehran J.' 'Park, Young S.' 'Lopez, Robert' 'Laidlaw, Dylan' 'Vargas, Eriberto' 'Ziller, Joseph W.' 'Gorodetsky, Alon A.' _publ_section_title ; An Aza-Diels-Alder Approach to Crowded Benzoquinolines. ; _journal_name_full 'Organic letters' _journal_paper_doi 10.1021/acs.orglett.5b02939 _journal_year 2015 _chemical_formula_sum 'C25 H28 Br N' _chemical_formula_weight 422.39 _chemical_name_systematic ; ? ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXTL _cell_angle_alpha 101.7992(5) _cell_angle_beta 91.9711(6) _cell_angle_gamma 102.7405(6) _cell_formula_units_Z 2 _cell_length_a 7.8355(4) _cell_length_b 11.0538(6) _cell_length_c 12.4164(7) _cell_measurement_reflns_used 9224 _cell_measurement_temperature 143(2) _cell_measurement_theta_max 28.28 _cell_measurement_theta_min 2.27 _cell_volume 1023.20(10) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 143(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.911 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0154 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 11883 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 28.38 _diffrn_reflns_theta_min 1.68 _exptl_absorpt_coefficient_mu 2.018 _exptl_absorpt_correction_T_max 0.5865 _exptl_absorpt_correction_T_min 0.5198 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details 'Bruker SADABS' _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description irregular _exptl_crystal_F_000 440 _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.391 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.112 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 356 _refine_ls_number_reflns 4673 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.112 _refine_ls_R_factor_all 0.0225 _refine_ls_R_factor_gt 0.0212 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0305P)^2^+0.2951P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0561 _refine_ls_wR_factor_ref 0.0567 _reflns_number_gt 4449 _reflns_number_total 4673 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL aag1 in P-1 CELL 0.71073 7.8355 11.0538 12.4164 101.7992 91.9711 102.7405 ZERR 2.00 0.0004 0.0006 0.0007 0.0005 0.0006 0.0006 LATT 1 SFAC C H N BR UNIT 50 56 2 2 TEMP -130.000 SIZE 0.296 0.367 0.373 rem D. Josh Dibble/ Alon Gorodetsky 15s sphere ccd2 rem APEX2 2011.4-1, SAINT 7.68a, SADABS 2008/1, SHELXTL 2008/4 L.S. 12 ACTA 51 FMAP 2 PLAN 6 WGHT 0.030500 0.295100 FVAR 0.24341 BR1 4 0.746742 0.121967 1.006078 11.00000 0.02906 0.02602 = 0.01527 0.00915 0.00569 0.00812 N1 3 0.828834 0.279594 0.563581 11.00000 0.01860 0.02192 = 0.01516 0.00691 0.00086 0.00538 C1 1 0.808464 0.246564 0.667148 11.00000 0.01932 0.01781 = 0.01438 0.00535 0.00064 0.00315 C2 1 0.680605 0.275354 0.734635 11.00000 0.02097 0.02387 = 0.02138 0.00887 0.00261 0.00973 C3 1 0.663655 0.236682 0.835423 11.00000 0.02164 0.02521 = 0.02009 0.00784 0.00656 0.00841 C4 1 0.775514 0.169459 0.867878 11.00000 0.02179 0.01800 = 0.01369 0.00593 0.00308 0.00367 C5 1 0.907430 0.133164 0.801220 11.00000 0.01818 0.01559 = 0.01608 0.00446 0.00085 0.00258 C6 1 1.022368 0.060291 0.830704 11.00000 0.02427 0.02104 = 0.01894 0.00824 0.00093 0.00674 C7 1 1.142854 0.025438 0.760918 11.00000 0.02757 0.02842 = 0.02574 0.01115 0.00357 0.01454 C8 1 1.154637 0.061110 0.658303 11.00000 0.02836 0.03166 = 0.02454 0.00979 0.01042 0.01550 C9 1 1.047497 0.133024 0.628126 11.00000 0.02520 0.02440 = 0.01795 0.00786 0.00550 0.00908 C10 1 0.921508 0.171704 0.698202 11.00000 0.01782 0.01621 = 0.01611 0.00449 0.00134 0.00322 C11 1 0.787859 0.380142 0.547513 11.00000 0.01836 0.02018 = 0.01568 0.00508 0.00093 0.00334 C12 1 0.799113 0.414999 0.439767 11.00000 0.01730 0.01746 = 0.01561 0.00543 -0.00015 0.00249 C13 1 0.886029 0.353600 0.356441 11.00000 0.01988 0.01941 = 0.01859 0.00597 -0.00004 0.00745 C14 1 0.896519 0.389784 0.256376 11.00000 0.01894 0.02079 = 0.01762 0.00487 0.00223 0.00741 C15 1 0.820559 0.486875 0.234773 11.00000 0.01623 0.01881 = 0.01591 0.00627 0.00013 0.00310 C16 1 0.733684 0.547249 0.317680 11.00000 0.02133 0.02000 = 0.02168 0.00850 0.00324 0.00904 C17 1 0.724795 0.512400 0.419429 11.00000 0.02214 0.02078 = 0.01795 0.00517 0.00467 0.00777 C18 1 0.842648 0.523207 0.124092 11.00000 0.02064 0.02295 = 0.01699 0.00840 0.00321 0.00792 C19 1 0.724453 0.604335 0.090187 11.00000 0.01874 0.01972 = 0.01654 0.00705 0.00192 0.00500 C20 1 0.763341 0.628856 -0.024301 11.00000 0.02014 0.02125 = 0.01690 0.00791 0.00167 0.00631 C21 1 0.652862 0.708687 -0.068597 11.00000 0.02082 0.01996 = 0.01786 0.00787 0.00147 0.00628 C22 1 0.700577 0.729183 -0.182529 11.00000 0.02298 0.02349 = 0.01866 0.00908 0.00366 0.00965 C23 1 0.590602 0.805145 -0.232554 11.00000 0.02049 0.02046 = 0.01723 0.00662 0.00174 0.00720 C24 1 0.640987 0.823152 -0.346333 11.00000 0.02695 0.02457 = 0.01754 0.00866 0.00378 0.01026 C25 1 0.537558 0.905368 -0.392735 11.00000 0.02925 0.02689 = 0.02214 0.01170 -0.00210 0.00688 H2A 2 0.595867 0.317020 0.709727 11.00000 0.03100 H3A 2 0.571992 0.258000 0.878978 11.00000 0.02897 H6A 2 1.016395 0.036331 0.898708 11.00000 0.02309 H7A 2 1.224362 -0.024963 0.776850 11.00000 0.02456 H8A 2 1.232516 0.034311 0.609666 11.00000 0.03233 H9A 2 1.053698 0.156504 0.562368 11.00000 0.03004 H11A 2 0.749192 0.440896 0.605962 11.00000 0.02580 H13A 2 0.938352 0.288531 0.368968 11.00000 0.02300 H14A 2 0.956914 0.348042 0.198858 11.00000 0.02322 H16A 2 0.683440 0.614254 0.306465 11.00000 0.02188 H17A 2 0.667711 0.557774 0.476449 11.00000 0.03068 H18A 2 0.824941 0.444972 0.067649 11.00000 0.02176 H18B 2 0.965082 0.567852 0.124376 11.00000 0.02554 H19A 2 0.743806 0.684565 0.142970 11.00000 0.02098 H19B 2 0.598873 0.559603 0.090781 11.00000 0.01664 H20A 2 0.888797 0.672125 -0.019973 11.00000 0.02233 H20B 2 0.746246 0.546385 -0.076214 11.00000 0.02240 H21A 2 0.528368 0.666542 -0.071811 11.00000 0.01792 H21B 2 0.669955 0.790374 -0.017251 11.00000 0.02338 H22A 2 0.687782 0.644954 -0.231273 11.00000 0.02689 H22B 2 0.822435 0.773944 -0.175411 11.00000 0.02534 H23A 2 0.465213 0.761778 -0.237353 11.00000 0.02383 H23B 2 0.606183 0.888674 -0.183323 11.00000 0.02427 H24A 2 0.618273 0.740082 -0.394774 11.00000 0.02790 H24B 2 0.765029 0.861758 -0.342336 11.00000 0.02625 H25A 2 0.568244 0.913470 -0.463715 11.00000 0.04604 H25B 2 0.563658 0.988555 -0.347126 11.00000 0.03166 H25C 2 0.411945 0.868473 -0.399577 11.00000 0.02878 HKLF 4 REM aag1 in P-1 REM R1 = 0.0212 for 4449 Fo > 4sig(Fo) and 0.0225 for all 4673 data REM 356 parameters refined using 0 restraints END WGHT 0.0305 0.2942 REM Highest difference peak 0.391, deepest hole -0.216, 1-sigma level 0.049 Q1 1 0.9177 0.1588 0.7520 11.00000 0.05 0.39 Q2 1 0.8289 0.1835 1.0033 11.00000 0.05 0.37 Q3 1 0.8255 0.5021 0.1828 11.00000 0.05 0.35 Q4 1 0.8306 0.3825 0.3931 11.00000 0.05 0.35 Q5 1 0.6700 0.0595 1.0125 11.00000 0.05 0.34 Q6 1 0.8580 0.1624 0.8371 11.00000 0.05 0.33 ; _cod_data_source_file ol5b02939_si_001.cif _cod_data_source_block aag1 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 1540739 loop_ _symmetry_equiv_pos_as_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_symmetry_multiplicity _atom_site_calc_flag Br1 Br 0.746742(17) 0.121967(12) 1.006078(10) 0.02240(5) Uani 1 1 d N1 N 0.82883(14) 0.27959(10) 0.56358(9) 0.0180(2) Uani 1 1 d C1 C 0.80846(16) 0.24656(12) 0.66715(10) 0.0171(2) Uani 1 1 d C2 C 0.68060(17) 0.27535(13) 0.73463(11) 0.0208(3) Uani 1 1 d C3 C 0.66366(17) 0.23668(13) 0.83542(11) 0.0213(3) Uani 1 1 d C4 C 0.77551(16) 0.16946(12) 0.86788(10) 0.0176(2) Uani 1 1 d C5 C 0.90743(16) 0.13316(11) 0.80122(10) 0.0167(2) Uani 1 1 d C6 C 1.02237(17) 0.06029(12) 0.83070(11) 0.0206(3) Uani 1 1 d C7 C 1.14285(19) 0.02544(14) 0.76092(12) 0.0252(3) Uani 1 1 d C8 C 1.15464(19) 0.06111(14) 0.65830(12) 0.0261(3) Uani 1 1 d C9 C 1.04750(18) 0.13302(13) 0.62813(11) 0.0214(3) Uani 1 1 d C10 C 0.92151(16) 0.17170(11) 0.69820(10) 0.0167(2) Uani 1 1 d C11 C 0.78786(16) 0.38014(12) 0.54751(10) 0.0181(2) Uani 1 1 d C12 C 0.79911(16) 0.41500(11) 0.43977(10) 0.0168(2) Uani 1 1 d C13 C 0.88603(17) 0.35360(12) 0.35644(10) 0.0186(2) Uani 1 1 d C14 C 0.89652(16) 0.38978(12) 0.25638(10) 0.0186(2) Uani 1 1 d C15 C 0.82056(16) 0.48687(12) 0.23477(10) 0.0168(2) Uani 1 1 d C16 C 0.73368(17) 0.54725(12) 0.31768(11) 0.0197(2) Uani 1 1 d C17 C 0.72479(17) 0.51240(12) 0.41943(11) 0.0196(2) Uani 1 1 d C18 C 0.84265(17) 0.52321(13) 0.12409(10) 0.0191(2) Uani 1 1 d C19 C 0.72445(16) 0.60433(12) 0.09019(10) 0.0178(2) Uani 1 1 d C20 C 0.76334(17) 0.62886(12) -0.02430(11) 0.0186(2) Uani 1 1 d C21 C 0.65286(17) 0.70869(12) -0.06860(10) 0.0188(2) Uani 1 1 d C22 C 0.70058(17) 0.72918(13) -0.18253(11) 0.0203(3) Uani 1 1 d C23 C 0.59060(17) 0.80515(12) -0.23255(10) 0.0186(2) Uani 1 1 d C24 C 0.64099(18) 0.82315(13) -0.34633(11) 0.0217(3) Uani 1 1 d C25 C 0.5376(2) 0.90537(14) -0.39273(12) 0.0252(3) Uani 1 1 d H2A H 0.596(2) 0.3170(16) 0.7097(15) 0.031(4) Uiso 1 1 d H3A H 0.572(2) 0.2580(16) 0.8790(15) 0.029(4) Uiso 1 1 d H6A H 1.016(2) 0.0363(15) 0.8987(14) 0.023(4) Uiso 1 1 d H7A H 1.224(2) -0.0250(16) 0.7769(14) 0.025(4) Uiso 1 1 d H8A H 1.233(2) 0.0343(16) 0.6097(15) 0.032(5) Uiso 1 1 d H9A H 1.054(2) 0.1565(17) 0.5624(15) 0.030(4) Uiso 1 1 d H11A H 0.749(2) 0.4409(16) 0.6060(14) 0.026(4) Uiso 1 1 d H13A H 0.938(2) 0.2885(16) 0.3690(14) 0.023(4) Uiso 1 1 d H14A H 0.957(2) 0.3480(15) 0.1989(14) 0.023(4) Uiso 1 1 d H16A H 0.683(2) 0.6143(15) 0.3065(13) 0.022(4) Uiso 1 1 d H17A H 0.668(2) 0.5578(16) 0.4764(14) 0.031(4) Uiso 1 1 d H18A H 0.825(2) 0.4450(16) 0.0676(13) 0.022(4) Uiso 1 1 d H18B H 0.965(2) 0.5679(16) 0.1244(14) 0.026(4) Uiso 1 1 d H19A H 0.744(2) 0.6846(15) 0.1430(13) 0.021(4) Uiso 1 1 d H19B H 0.599(2) 0.5596(14) 0.0908(12) 0.017(4) Uiso 1 1 d H20A H 0.889(2) 0.6721(15) -0.0200(13) 0.022(4) Uiso 1 1 d H20B H 0.746(2) 0.5464(16) -0.0762(13) 0.022(4) Uiso 1 1 d H21A H 0.528(2) 0.6665(14) -0.0718(12) 0.018(4) Uiso 1 1 d H21B H 0.670(2) 0.7904(16) -0.0173(14) 0.023(4) Uiso 1 1 d H22A H 0.688(2) 0.6450(16) -0.2313(14) 0.027(4) Uiso 1 1 d H22B H 0.822(2) 0.7739(16) -0.1754(14) 0.025(4) Uiso 1 1 d H23A H 0.465(2) 0.7618(15) -0.2374(13) 0.024(4) Uiso 1 1 d H23B H 0.606(2) 0.8887(16) -0.1833(14) 0.024(4) Uiso 1 1 d H24A H 0.618(2) 0.7401(17) -0.3948(14) 0.028(4) Uiso 1 1 d H24B H 0.765(2) 0.8618(16) -0.3423(14) 0.026(4) Uiso 1 1 d H25A H 0.568(3) 0.9135(19) -0.4637(18) 0.046(6) Uiso 1 1 d H25B H 0.564(2) 0.9886(18) -0.3471(15) 0.032(5) Uiso 1 1 d H25C H 0.412(2) 0.8685(16) -0.3996(14) 0.029(4) 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 0.02906(8) 0.02602(8) 0.01527(7) 0.00915(5) 0.00569(5) 0.00812(5) N1 0.0186(5) 0.0219(5) 0.0152(5) 0.0069(4) 0.0009(4) 0.0054(4) C1 0.0193(6) 0.0178(6) 0.0144(5) 0.0054(4) 0.0006(4) 0.0032(4) C2 0.0210(6) 0.0239(6) 0.0214(6) 0.0089(5) 0.0026(5) 0.0097(5) C3 0.0216(6) 0.0252(6) 0.0201(6) 0.0078(5) 0.0066(5) 0.0084(5) C4 0.0218(6) 0.0180(6) 0.0137(5) 0.0059(4) 0.0031(4) 0.0037(5) C5 0.0182(6) 0.0156(5) 0.0161(6) 0.0045(4) 0.0008(4) 0.0026(4) C6 0.0243(6) 0.0210(6) 0.0189(6) 0.0082(5) 0.0009(5) 0.0067(5) C7 0.0276(7) 0.0284(7) 0.0257(7) 0.0111(5) 0.0036(5) 0.0145(6) C8 0.0284(7) 0.0317(7) 0.0245(7) 0.0098(6) 0.0104(6) 0.0155(6) C9 0.0252(6) 0.0244(6) 0.0179(6) 0.0079(5) 0.0055(5) 0.0091(5) C10 0.0178(6) 0.0162(5) 0.0161(6) 0.0045(4) 0.0013(4) 0.0032(4) C11 0.0184(6) 0.0202(6) 0.0157(6) 0.0051(5) 0.0009(4) 0.0033(5) C12 0.0173(5) 0.0175(6) 0.0156(6) 0.0054(4) -0.0001(4) 0.0025(4) C13 0.0199(6) 0.0194(6) 0.0186(6) 0.0060(5) 0.0000(5) 0.0075(5) C14 0.0189(6) 0.0208(6) 0.0176(6) 0.0049(5) 0.0022(5) 0.0074(5) C15 0.0162(5) 0.0188(6) 0.0159(6) 0.0063(5) 0.0001(4) 0.0031(4) C16 0.0213(6) 0.0200(6) 0.0217(6) 0.0085(5) 0.0032(5) 0.0090(5) C17 0.0221(6) 0.0208(6) 0.0180(6) 0.0052(5) 0.0047(5) 0.0078(5) C18 0.0206(6) 0.0230(6) 0.0170(6) 0.0084(5) 0.0032(5) 0.0079(5) C19 0.0187(6) 0.0197(6) 0.0165(6) 0.0071(5) 0.0019(4) 0.0050(5) C20 0.0201(6) 0.0213(6) 0.0169(6) 0.0079(5) 0.0017(4) 0.0063(5) C21 0.0208(6) 0.0200(6) 0.0179(6) 0.0079(5) 0.0015(5) 0.0063(5) C22 0.0230(6) 0.0235(6) 0.0187(6) 0.0091(5) 0.0037(5) 0.0096(5) C23 0.0205(6) 0.0205(6) 0.0172(6) 0.0066(5) 0.0017(5) 0.0072(5) C24 0.0270(7) 0.0246(6) 0.0175(6) 0.0087(5) 0.0038(5) 0.0103(5) C25 0.0292(7) 0.0269(7) 0.0221(7) 0.0117(6) -0.0021(5) 0.0069(6) 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 C11 N1 C1 119.74(11) C2 C1 N1 123.73(11) C2 C1 C10 119.42(11) N1 C1 C10 116.71(11) C1 C2 C3 121.12(12) C4 C3 C2 119.87(12) C3 C4 C5 122.21(11) C3 C4 Br1 117.60(9) C5 C4 Br1 120.18(9) C6 C5 C4 123.77(11) C6 C5 C10 118.96(11) C4 C5 C10 117.26(11) C7 C6 C5 120.64(12) C6 C7 C8 120.52(12) C9 C8 C7 120.28(13) C8 C9 C10 121.01(12) C9 C10 C5 118.57(11) C9 C10 C1 121.39(11) C5 C10 C1 120.04(11) N1 C11 C12 121.59(12) C17 C12 C13 118.72(11) C17 C12 C11 119.91(11) C13 C12 C11 121.36(11) C14 C13 C12 120.00(11) C13 C14 C15 121.67(12) C16 C15 C14 118.11(11) C16 C15 C18 123.58(11) C14 C15 C18 118.27(11) C15 C16 C17 120.49(11) C12 C17 C16 120.99(12) C15 C18 C19 117.61(11) C18 C19 C20 109.97(10) C21 C20 C19 115.35(11) C22 C21 C20 111.96(10) C21 C22 C23 114.33(11) C24 C23 C22 112.93(11) C23 C24 C25 112.49(11) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C4 1.9010(12) N1 C11 1.2735(17) N1 C1 1.4117(15) C1 C2 1.3771(18) C1 C10 1.4312(17) C2 C3 1.4041(18) C3 C4 1.3668(18) C4 C5 1.4214(17) C5 C6 1.4184(17) C5 C10 1.4288(16) C6 C7 1.3677(19) C7 C8 1.4089(19) C8 C9 1.3680(19) C9 C10 1.4169(17) C11 C12 1.4663(17) C12 C17 1.3927(17) C12 C13 1.4000(18) C13 C14 1.3806(17) C14 C15 1.4023(17) C15 C16 1.3914(18) C15 C18 1.5137(17) C16 C17 1.3938(17) C18 C19 1.5274(17) C19 C20 1.5291(17) C20 C21 1.5275(17) C21 C22 1.5239(17) C22 C23 1.5261(17) C23 C24 1.5199(17) C24 C25 1.5236(18)