#------------------------------------------------------------------------------ #$Date: 2023-11-10 04:20:50 +0200 (Fri, 10 Nov 2023) $ #$Revision: 287507 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/76/7247698.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_7247698 loop_ _publ_author_name 'Zheng, Yongpeng' 'Li, Jianxiao' 'Qi, Chaorong' 'Wu, Wanqing' 'Jiang, Huanfeng' _publ_section_title ; Rapid assembly of structurally diverse cyanamides and disulfanes via base-mediated aminoalkylation of aryl thiourea ; _journal_issue 47 _journal_name_full 'RSC Advances' _journal_page_first 33047 _journal_page_last 33052 _journal_paper_doi 10.1039/D3RA06051A _journal_volume 13 _journal_year 2023 _chemical_formula_moiety 'C16 H12 Br F3 N2' _chemical_formula_sum 'C16 H12 Br F3 N2' _chemical_formula_weight 369.19 _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 geom _atom_sites_solution_primary dual _audit_creation_date 2022-12-04 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2023-02-14 deposited with the CCDC. 2023-10-31 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.730(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.1120(5) _cell_length_b 7.3561(3) _cell_length_c 18.2597(6) _cell_measurement_reflns_used 4749 _cell_measurement_temperature 170 _cell_measurement_theta_max 26.32 _cell_measurement_theta_min 3.057 _cell_volume 1603.48(11) _computing_cell_refinement 'SAINT V8.40A (?, 2016)' _computing_data_reduction 'SAINT V8.40A (?, 2016)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 170.0 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'D8 VENTURE' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0502 _diffrn_reflns_av_unetI/netI 0.0496 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 11895 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.397 _diffrn_reflns_theta_min 2.594 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 2.591 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.5134 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1076 before and 0.0574 after correction. The Ratio of minimum to maximum transmission is 0.6888. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.529 _exptl_crystal_description block _exptl_crystal_F_000 736 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.294 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.070 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3232 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0485 _refine_ls_R_factor_gt 0.0330 _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^)+(0.0272P)^2^+0.6806P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0693 _refine_ls_wR_factor_ref 0.0772 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2594 _reflns_number_total 3232 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL 124z108612_0m_a.res in P2(1)/c 124z108612_0m.res created by SHELXL-2018/3 at 15:28:17 on 04-Dec-2022 REM Old TITL 124z108612_0m in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.133, Rweak 0.006, Alpha 0.036, Orientation as input REM Formula found by SHELXT: C16 N2 F3 Br CELL 0.71073 12.112 7.3561 18.2597 90 99.73 90 ZERR 4 0.0005 0.0003 0.0006 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br F N UNIT 64 48 4 12 8 L.S. 4 PLAN 20 SIZE 0.19 0.08 0.05 TEMP -103.15 BOND $H list 4 fmap 2 ACTA OMIT -9 0 20 REM REM REM WGHT 0.027200 0.680600 FVAR 0.62970 BR1 3 0.890662 -0.335183 0.582708 11.00000 0.04134 0.02804 = 0.02943 0.00897 0.00350 0.00052 F3 4 0.778001 0.042858 0.617044 11.00000 0.09401 0.06402 = 0.03239 -0.00746 0.02729 0.00751 F2 4 0.653715 -0.135417 0.559023 11.00000 0.04723 0.08181 = 0.06165 0.02115 0.03178 -0.00161 N1 5 0.832308 0.162147 0.312297 11.00000 0.02578 0.01679 = 0.02392 0.00106 0.00871 0.00404 F1 4 0.651693 0.146832 0.531125 11.00000 0.09677 0.09162 = 0.06969 0.03991 0.06287 0.06387 C6 1 0.848056 0.053237 0.376998 11.00000 0.02337 0.01551 = 0.02004 -0.00259 0.00304 -0.00217 C3 1 0.871454 -0.171110 0.501193 11.00000 0.02860 0.01943 = 0.02090 0.00161 -0.00073 -0.00162 N2 5 0.947626 0.108705 0.214053 11.00000 0.05124 0.03071 = 0.03546 0.00128 0.02293 0.00289 C1 1 0.927410 -0.084362 0.385786 11.00000 0.02408 0.01936 = 0.02411 -0.00506 0.00777 -0.00154 AFIX 43 H1 2 0.973856 -0.102380 0.349375 11.00000 -1.20000 AFIX 0 C4 1 0.793618 -0.031355 0.493279 11.00000 0.02738 0.02427 = 0.02448 0.00019 0.00842 0.00185 C10 1 0.707982 0.635964 0.321519 11.00000 0.02066 0.01689 = 0.03083 -0.00510 -0.00027 -0.00207 C5 1 0.782334 0.081336 0.431408 11.00000 0.02565 0.02014 = 0.02684 -0.00102 0.00756 0.00451 AFIX 43 H5 2 0.729516 0.177914 0.426283 11.00000 -1.20000 AFIX 0 C2 1 0.938717 -0.195368 0.447787 11.00000 0.02230 0.01585 = 0.02953 -0.00221 0.00096 0.00306 AFIX 43 H2 2 0.993302 -0.289344 0.453761 11.00000 -1.20000 AFIX 0 C8 1 0.749578 0.310930 0.298896 11.00000 0.02410 0.01815 = 0.02532 0.00116 0.00291 0.00348 AFIX 23 H8A 2 0.679487 0.272127 0.315439 11.00000 -1.20000 H8B 2 0.732072 0.336074 0.244915 11.00000 -1.20000 AFIX 0 C9 1 0.792208 0.484773 0.339823 11.00000 0.02059 0.01757 = 0.03806 -0.00113 0.00181 0.00158 AFIX 23 H9A 2 0.805594 0.462353 0.394062 11.00000 -1.20000 H9B 2 0.864173 0.521079 0.325263 11.00000 -1.20000 AFIX 0 C7 1 0.895564 0.132722 0.260059 11.00000 0.03483 0.01465 = 0.02710 0.00132 0.00681 0.00064 C15 1 0.629945 0.673033 0.366946 11.00000 0.02852 0.03096 = 0.04297 -0.00285 0.00981 -0.00230 AFIX 43 H15 2 0.630022 0.603637 0.410832 11.00000 -1.20000 AFIX 0 C11 1 0.704808 0.737778 0.257295 11.00000 0.03788 0.02234 = 0.03385 -0.00174 0.00142 -0.00695 AFIX 43 H11 2 0.757367 0.713941 0.225321 11.00000 -1.20000 AFIX 0 C13 1 0.549890 0.909750 0.284867 11.00000 0.03166 0.02558 = 0.08221 -0.00755 -0.01901 0.00687 AFIX 43 H13 2 0.495840 1.003173 0.272354 11.00000 -1.20000 AFIX 0 C12 1 0.625666 0.874189 0.239193 11.00000 0.05060 0.02198 = 0.04980 0.00628 -0.01691 -0.00493 AFIX 43 H12 2 0.624228 0.942867 0.194981 11.00000 -1.20000 AFIX 0 C14 1 0.551610 0.810774 0.348872 11.00000 0.02863 0.04247 = 0.07447 -0.02079 0.01140 0.00634 AFIX 43 H14 2 0.499227 0.836541 0.380765 11.00000 -1.20000 AFIX 0 C16 1 0.719660 0.004561 0.549885 11.00000 0.05484 0.04614 = 0.03739 0.01189 0.02269 0.01543 HKLF 4 REM 124z108612_0m_a.res in P2(1)/c REM wR2 = 0.0772, GooF = S = 1.037, Restrained GooF = 1.037 for all data REM R1 = 0.0330 for 2594 Fo > 4sig(Fo) and 0.0485 for all 3232 data REM 199 parameters refined using 0 restraints END WGHT 0.0285 0.6421 REM Highest difference peak 0.294, deepest hole -0.472, 1-sigma level 0.070 Q1 1 0.8039 -0.1482 0.4879 11.00000 0.05 0.29 Q2 1 1.0679 -0.3019 0.4843 11.00000 0.05 0.29 Q3 1 0.8594 -0.2386 0.5222 11.00000 0.05 0.27 Q4 1 0.7519 0.5725 0.3333 11.00000 0.05 0.26 Q5 1 0.9994 -0.3823 0.5904 11.00000 0.05 0.26 Q6 1 0.7732 0.3882 0.3292 11.00000 0.05 0.26 Q7 1 0.8808 -0.2077 0.4653 11.00000 0.05 0.25 Q8 1 0.4352 0.7579 0.2639 11.00000 0.05 0.24 Q9 1 0.9147 0.6546 0.3268 11.00000 0.05 0.24 Q10 1 0.8402 -0.0859 0.5008 11.00000 0.05 0.24 Q11 1 0.9195 0.3337 0.4114 11.00000 0.05 0.23 Q12 1 0.7933 0.2542 0.3081 11.00000 0.05 0.22 Q13 1 0.9373 0.5025 0.3839 11.00000 0.05 0.21 Q14 1 0.6033 0.0775 0.4607 11.00000 0.05 0.21 Q15 1 0.5392 -0.1348 0.4982 11.00000 0.05 0.21 Q16 1 0.6405 0.1914 0.4731 11.00000 0.05 0.21 Q17 1 0.8258 0.8379 0.2712 11.00000 0.05 0.21 Q18 1 0.9602 0.0018 0.1841 11.00000 0.05 0.21 Q19 1 0.5348 0.2227 0.5426 11.00000 0.05 0.20 Q20 1 0.7272 0.0385 0.2748 11.00000 0.05 0.20 REM The information below was added by Olex2. REM REM R1 = 0.0330 for 2594 Fo > 4sig(Fo) and 0.0485 for all 12355 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.29, deepest hole -0.47 REM Mean Shift 0, Max Shift -0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0485 REM R1_gt = 0.0330 REM wR_ref = 0.0772 REM GOOF = 1.037 REM Shift_max = -0.001 REM Shift_mean = 0 REM Reflections_all = 12355 REM Reflections_gt = 2594 REM Parameters = n/a REM Hole = -0.47 REM Peak = 0.29 REM Flack = n/a ; _cod_data_source_file d3ra06051a2.cif _cod_data_source_block 124z108612_0m _cod_database_code 7247698 _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. ; _shelx_estimated_absorpt_t_max 0.881 _shelx_estimated_absorpt_t_min 0.639 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C8(H8A,H8B), C9(H9A,H9B) 2.b Aromatic/amide H refined with riding coordinates: C1(H1), C5(H5), C2(H2), C15(H15), C11(H11), C13(H13), C12(H12), C14(H14) ; _olex2_submission_special_instructions 'No special instructions were received' 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 0.89066(2) -0.33518(3) 0.58271(2) 0.03323(10) Uani 1 1 d . . . . . F3 F 0.77800(18) 0.0429(2) 0.61704(10) 0.0615(5) Uani 1 1 d . . . . . F2 F 0.65371(16) -0.1354(3) 0.55902(11) 0.0609(5) Uani 1 1 d . . . . . N1 N 0.83231(16) 0.1621(2) 0.31230(11) 0.0216(4) Uani 1 1 d . . . . . F1 F 0.6517(2) 0.1468(3) 0.53112(12) 0.0804(8) Uani 1 1 d . . . . . C6 C 0.84806(19) 0.0532(3) 0.37700(12) 0.0197(5) Uani 1 1 d . . . . . C3 C 0.8715(2) -0.1711(3) 0.50119(13) 0.0235(5) Uani 1 1 d . . . . . N2 N 0.9476(2) 0.1087(3) 0.21405(13) 0.0373(6) Uani 1 1 d . . . . . C1 C 0.9274(2) -0.0844(3) 0.38579(13) 0.0221(5) Uani 1 1 d . . . . . H1 H 0.973856 -0.102380 0.349375 0.027 Uiso 1 1 calc R . . . . C4 C 0.7936(2) -0.0314(3) 0.49328(13) 0.0249(5) Uani 1 1 d . . . . . C10 C 0.7080(2) 0.6360(3) 0.32152(14) 0.0233(5) Uani 1 1 d . . . . . C5 C 0.7823(2) 0.0813(3) 0.43141(13) 0.0238(5) Uani 1 1 d . . . . . H5 H 0.729516 0.177914 0.426283 0.029 Uiso 1 1 calc R . . . . C2 C 0.9387(2) -0.1954(3) 0.44779(13) 0.0230(5) Uani 1 1 d . . . . . H2 H 0.993302 -0.289344 0.453761 0.028 Uiso 1 1 calc R . . . . C8 C 0.7496(2) 0.3109(3) 0.29890(13) 0.0227(5) Uani 1 1 d . . . . . H8A H 0.679487 0.272127 0.315439 0.027 Uiso 1 1 calc R . . . . H8B H 0.732072 0.336074 0.244915 0.027 Uiso 1 1 calc R . . . . C9 C 0.7922(2) 0.4848(3) 0.33982(14) 0.0258(5) Uani 1 1 d . . . . . H9A H 0.805594 0.462353 0.394062 0.031 Uiso 1 1 calc R . . . . H9B H 0.864173 0.521079 0.325263 0.031 Uiso 1 1 calc R . . . . C7 C 0.8956(2) 0.1327(3) 0.26006(14) 0.0253(5) Uani 1 1 d . . . . . C15 C 0.6299(2) 0.6730(3) 0.36695(16) 0.0337(6) Uani 1 1 d . . . . . H15 H 0.630022 0.603637 0.410832 0.040 Uiso 1 1 calc R . . . . C11 C 0.7048(2) 0.7378(3) 0.25730(15) 0.0319(6) Uani 1 1 d . . . . . H11 H 0.757367 0.713941 0.225321 0.038 Uiso 1 1 calc R . . . . C13 C 0.5499(3) 0.9098(4) 0.2849(2) 0.0498(9) Uani 1 1 d . . . . . H13 H 0.495840 1.003173 0.272354 0.060 Uiso 1 1 calc R . . . . C12 C 0.6257(3) 0.8742(3) 0.23919(18) 0.0437(8) Uani 1 1 d . . . . . H12 H 0.624228 0.942867 0.194981 0.052 Uiso 1 1 calc R . . . . C14 C 0.5516(2) 0.8108(4) 0.3489(2) 0.0482(8) Uani 1 1 d . . . . . H14 H 0.499227 0.836541 0.380765 0.058 Uiso 1 1 calc R . . . . C16 C 0.7197(3) 0.0046(4) 0.54989(16) 0.0444(7) Uani 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 0.04134(18) 0.02804(15) 0.02943(16) 0.00897(11) 0.00350(11) 0.00052(12) F3 0.0940(15) 0.0640(12) 0.0324(11) -0.0075(8) 0.0273(10) 0.0075(11) F2 0.0472(11) 0.0818(13) 0.0616(13) 0.0212(10) 0.0318(10) -0.0016(10) N1 0.0258(11) 0.0168(9) 0.0239(10) 0.0011(8) 0.0087(8) 0.0040(8) F1 0.0968(17) 0.0916(15) 0.0697(15) 0.0399(12) 0.0629(13) 0.0639(13) C6 0.0234(12) 0.0155(10) 0.0200(12) -0.0026(8) 0.0030(9) -0.0022(9) C3 0.0286(13) 0.0194(11) 0.0209(12) 0.0016(9) -0.0007(9) -0.0016(10) N2 0.0512(15) 0.0307(12) 0.0355(14) 0.0013(10) 0.0229(12) 0.0029(11) C1 0.0241(13) 0.0194(11) 0.0241(13) -0.0051(9) 0.0078(10) -0.0015(10) C4 0.0274(13) 0.0243(12) 0.0245(13) 0.0002(10) 0.0084(10) 0.0018(10) C10 0.0207(12) 0.0169(11) 0.0308(14) -0.0051(9) -0.0003(10) -0.0021(9) C5 0.0257(13) 0.0201(11) 0.0268(13) -0.0010(9) 0.0076(10) 0.0045(10) C2 0.0223(12) 0.0159(11) 0.0295(13) -0.0022(9) 0.0010(10) 0.0031(9) C8 0.0241(13) 0.0181(11) 0.0253(13) 0.0012(9) 0.0029(9) 0.0035(10) C9 0.0206(12) 0.0176(11) 0.0381(14) -0.0011(10) 0.0018(10) 0.0016(10) C7 0.0348(14) 0.0147(11) 0.0271(14) 0.0013(9) 0.0068(11) 0.0006(10) C15 0.0285(14) 0.0310(14) 0.0430(16) -0.0028(12) 0.0098(12) -0.0023(12) C11 0.0379(16) 0.0223(12) 0.0338(15) -0.0017(10) 0.0014(12) -0.0070(12) C13 0.0317(17) 0.0256(14) 0.082(3) -0.0076(15) -0.0190(17) 0.0069(13) C12 0.051(2) 0.0220(13) 0.0498(19) 0.0063(12) -0.0169(15) -0.0049(13) C14 0.0286(16) 0.0425(17) 0.074(2) -0.0208(16) 0.0114(15) 0.0063(14) C16 0.0548(19) 0.0461(17) 0.0374(17) 0.0119(14) 0.0227(14) 0.0154(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' 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 C6 N1 C8 123.42(19) . . ? C7 N1 C6 119.44(19) . . ? C7 N1 C8 117.14(19) . . ? C1 C6 N1 120.2(2) . . ? C1 C6 C5 119.7(2) . . ? C5 C6 N1 120.0(2) . . ? C4 C3 Br1 122.96(18) . . ? C2 C3 Br1 117.48(17) . . ? C2 C3 C4 119.6(2) . . ? C6 C1 H1 120.1 . . ? C2 C1 C6 119.8(2) . . ? C2 C1 H1 120.1 . . ? C3 C4 C5 119.9(2) . . ? C3 C4 C16 122.2(2) . . ? C5 C4 C16 117.8(2) . . ? C15 C10 C9 121.1(2) . . ? C15 C10 C11 118.4(2) . . ? C11 C10 C9 120.5(2) . . ? C6 C5 H5 119.9 . . ? C4 C5 C6 120.2(2) . . ? C4 C5 H5 119.9 . . ? C3 C2 H2 119.6 . . ? C1 C2 C3 120.8(2) . . ? C1 C2 H2 119.6 . . ? N1 C8 H8A 109.2 . . ? N1 C8 H8B 109.2 . . ? N1 C8 C9 112.09(19) . . ? H8A C8 H8B 107.9 . . ? C9 C8 H8A 109.2 . . ? C9 C8 H8B 109.2 . . ? C10 C9 C8 110.44(19) . . ? C10 C9 H9A 109.6 . . ? C10 C9 H9B 109.6 . . ? C8 C9 H9A 109.6 . . ? C8 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? N2 C7 N1 178.4(3) . . ? C10 C15 H15 119.7 . . ? C10 C15 C14 120.6(3) . . ? C14 C15 H15 119.7 . . ? C10 C11 H11 119.6 . . ? C10 C11 C12 120.7(3) . . ? C12 C11 H11 119.6 . . ? C12 C13 H13 119.9 . . ? C12 C13 C14 120.2(3) . . ? C14 C13 H13 119.9 . . ? C11 C12 H12 120.0 . . ? C13 C12 C11 120.1(3) . . ? C13 C12 H12 120.0 . . ? C15 C14 H14 120.0 . . ? C13 C14 C15 120.0(3) . . ? C13 C14 H14 120.0 . . ? F3 C16 F1 106.0(3) . . ? F3 C16 C4 112.6(3) . . ? F2 C16 F3 106.5(2) . . ? F2 C16 F1 106.3(3) . . ? F2 C16 C4 113.0(2) . . ? F1 C16 C4 111.9(2) . . ? 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 C3 1.900(2) . ? F3 C16 1.338(4) . ? F2 C16 1.331(3) . ? N1 C6 1.413(3) . ? N1 C8 1.476(3) . ? N1 C7 1.338(3) . ? F1 C16 1.340(3) . ? C6 C1 1.386(3) . ? C6 C5 1.390(3) . ? C3 C4 1.386(3) . ? C3 C2 1.384(3) . ? N2 C7 1.146(3) . ? C1 H1 0.9500 . ? C1 C2 1.384(3) . ? C4 C5 1.389(3) . ? C4 C16 1.501(4) . ? C10 C9 1.508(3) . ? C10 C15 1.386(4) . ? C10 C11 1.387(4) . ? C5 H5 0.9500 . ? C2 H2 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C8 C9 1.526(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C15 H15 0.9500 . ? C15 C14 1.389(4) . ? C11 H11 0.9500 . ? C11 C12 1.389(4) . ? C13 H13 0.9500 . ? C13 C12 1.366(5) . ? C13 C14 1.374(5) . ? C12 H12 0.9500 . ? C14 H14 0.9500 . ?