#------------------------------------------------------------------------------ #$Date: 2021-06-05 22:29:16 +0300 (Sat, 05 Jun 2021) $ #$Revision: 266172 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158015.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_7158015 loop_ _publ_author_name 'Jin, Jiang' 'Li, Yinghua' 'Xiang, Shiqun' 'Fan, Weibin' 'Guo, Shiwei' 'Huang, Deguang' _publ_section_title ; Selectfluor facilitated bridging of indoles to bis(indolyl)methanes using methyl tert-butyl ether as a new methylene precursor. ; _journal_issue 18 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4076 _journal_page_last 4081 _journal_paper_doi 10.1039/d1ob00120e _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C21 H20 F2 N2' _chemical_formula_sum 'C21 H20 F2 N2' _chemical_formula_weight 338.39 _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 geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-01-15 deposited with the CCDC. 2021-04-06 downloaded from the CCDC. ; _cell_angle_alpha 86.424(5) _cell_angle_beta 84.971(6) _cell_angle_gamma 85.252(6) _cell_formula_units_Z 2 _cell_length_a 7.9071(6) _cell_length_b 8.9267(5) _cell_length_c 11.6792(7) _cell_measurement_reflns_used 2659 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 72.4020 _cell_measurement_theta_min 3.7650 _cell_volume 817.11(9) _computing_cell_refinement 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 10.5594 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0198 _diffrn_reflns_av_unetI/netI 0.0266 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5413 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 69.939 _diffrn_reflns_theta_min 3.805 _diffrn_source 'micro-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.84571 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.375 _exptl_crystal_density_method 'Not Measured' _exptl_crystal_description block _exptl_crystal_F_000 356 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.589 _refine_diff_density_min -0.606 _refine_diff_density_rms 0.066 _refine_ls_extinction_coef 0.0048(17) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 3056 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.207 _refine_ls_R_factor_all 0.0695 _refine_ls_R_factor_gt 0.0605 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0993P)^2^+0.7951P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1768 _refine_ls_wR_factor_ref 0.1855 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2619 _reflns_number_total 3056 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00120e2.cif _cod_data_source_block Compound3l _cod_depositor_comments 'Adding full bibliography for 7158011--7158015.cif.' _cod_database_code 7158015 _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_min 0.857 _shelx_estimated_absorpt_t_max 0.890 _shelx_res_file ; TITL full.res in P-1 full.res created by SHELXL-2018/3 at 22:19:40 on 18-Nov-2020 CELL 1.54184 7.9071 8.9267 11.6792 86.424 84.971 85.252 ZERR 2 0.0006 0.0005 0.0007 0.005 0.006 0.006 LATT 1 SFAC C H F N UNIT 42 40 4 4 TEMP -173 SIZE 0.20 0.15 0.20 DFIX 2.1 0.01 H20a H21A OMIT 0 140 L.S. 4 PLAN 4 fmap 2 MORE -1 BOND $H ACTA CONF WGHT 0.099300 0.795100 EXTI 0.004776 FVAR 12.22681 F1 3 -0.043901 0.345888 0.642655 11.00000 0.03267 0.04924 = 0.03734 0.00084 0.00813 -0.00004 F2 3 0.028190 0.098540 0.145537 11.00000 0.03218 0.04666 = 0.04251 -0.00288 -0.00190 -0.02079 N1 4 0.618914 0.154721 0.534807 11.00000 0.03260 0.02401 = 0.02256 -0.00094 -0.00765 -0.00037 N2 4 0.641096 0.322609 0.018898 11.00000 0.02368 0.02894 = 0.02123 -0.00087 0.00070 -0.00213 C1 1 0.655942 0.247357 0.437848 11.00000 0.03058 0.02340 = 0.02050 -0.00432 -0.00569 -0.00341 C2 1 0.512513 0.336272 0.411635 11.00000 0.02715 0.02365 = 0.01871 -0.00366 -0.00463 -0.00461 C3 1 0.380317 0.299791 0.497951 11.00000 0.02999 0.02024 = 0.01949 -0.00524 -0.00521 -0.00391 C4 1 0.210803 0.355307 0.520901 11.00000 0.02847 0.02660 = 0.02306 -0.00171 -0.00287 -0.00393 AFIX 43 H4A 2 0.159517 0.433456 0.473457 11.00000 -1.20000 AFIX 0 C5 1 0.121850 0.291126 0.615662 11.00000 0.02898 0.03398 = 0.02733 -0.00546 0.00099 -0.00408 C6 1 0.187139 0.174594 0.687629 11.00000 0.04103 0.03438 = 0.02104 -0.00186 0.00053 -0.01177 AFIX 43 H6A 2 0.117799 0.133805 0.750566 11.00000 -1.20000 AFIX 0 C7 1 0.355331 0.118821 0.666001 11.00000 0.04307 0.02619 = 0.02040 -0.00154 -0.00650 -0.00679 AFIX 43 H7A 2 0.403617 0.038762 0.713163 11.00000 -1.20000 AFIX 0 C8 1 0.451123 0.183925 0.572959 11.00000 0.03331 0.02182 = 0.02064 -0.00391 -0.00679 -0.00556 C9 1 0.737569 0.047642 0.591460 11.00000 0.04147 0.03115 = 0.03163 0.00105 -0.01515 0.00157 AFIX 33 H9A 2 0.849576 0.046528 0.548205 11.00000 -1.50000 H9B 2 0.747143 0.077270 0.669888 11.00000 -1.50000 H9C 2 0.695980 -0.053058 0.594477 11.00000 -1.50000 AFIX 0 C10 1 0.829731 0.243012 0.377684 11.00000 0.02751 0.03662 = 0.03117 -0.00428 -0.00476 -0.00002 AFIX 33 H10A 2 0.904680 0.167563 0.417153 11.00000 -1.50000 H10B 2 0.824751 0.216471 0.297949 11.00000 -1.50000 H10C 2 0.874356 0.342136 0.378279 11.00000 -1.50000 AFIX 0 C11 1 0.497427 0.451388 0.311333 11.00000 0.02613 0.02260 = 0.02215 -0.00212 -0.00421 -0.00296 AFIX 23 H11A 2 0.382627 0.505017 0.318732 11.00000 -1.20000 H11B 2 0.581565 0.526486 0.316104 11.00000 -1.20000 AFIX 0 C12 1 0.661022 0.401658 0.114404 11.00000 0.02331 0.02145 = 0.02414 0.00198 -0.00490 -0.00110 C13 1 0.525249 0.386130 0.194505 11.00000 0.02274 0.02091 = 0.02134 0.00059 -0.00382 -0.00158 C14 1 0.413008 0.293845 0.146113 11.00000 0.02291 0.01925 = 0.02007 0.00133 -0.00481 0.00074 C15 1 0.253680 0.240825 0.184012 11.00000 0.02428 0.02638 = 0.02173 0.00001 -0.00190 -0.00255 AFIX 43 H15A 2 0.197465 0.264660 0.256609 11.00000 -1.20000 AFIX 0 C16 1 0.183134 0.152845 0.110994 11.00000 0.02350 0.02911 = 0.03174 0.00404 -0.00599 -0.00701 C17 1 0.257341 0.115635 0.002970 11.00000 0.03486 0.02704 = 0.02864 -0.00461 -0.01089 -0.00440 AFIX 43 H17A 2 0.201550 0.055145 -0.043764 11.00000 -1.20000 AFIX 0 C18 1 0.412634 0.167608 -0.035296 11.00000 0.03265 0.02971 = 0.02170 -0.00425 -0.00512 0.00112 AFIX 43 H18A 2 0.466172 0.143836 -0.108654 11.00000 -1.20000 AFIX 0 C19 1 0.489413 0.256246 0.036619 11.00000 0.02385 0.02376 = 0.02177 0.00130 -0.00393 0.00013 C20 1 0.758813 0.309702 -0.084119 11.00000 0.03083 0.03766 = 0.02601 -0.00199 0.00624 -0.00098 AFIX 33 H20A 2 0.857487 0.366775 -0.076380 11.00000 -1.50000 H20B 2 0.796896 0.203561 -0.093515 11.00000 -1.50000 H20C 2 0.701092 0.350104 -0.151628 11.00000 -1.50000 AFIX 0 C21 1 0.815004 0.489327 0.118000 11.00000 0.02431 0.02993 = 0.03253 0.00230 -0.00171 -0.00520 AFIX 33 H21A 2 0.888902 0.477286 0.046780 11.00000 -1.50000 H21B 2 0.778586 0.596135 0.125570 11.00000 -1.50000 H21C 2 0.877738 0.451615 0.183990 11.00000 -1.50000 AFIX 0 HKLF 4 REM full.res in P-1 REM wR2 = 0.1855, GooF = S = 1.092, Restrained GooF = 1.207 for all data REM R1 = 0.0605 for 2619 Fo > 4sig(Fo) and 0.0695 for all 3056 data REM 227 parameters refined using 1 restraints END WGHT 0.0993 0.7941 REM Highest difference peak 0.589, deepest hole -0.606, 1-sigma level 0.066 Q1 1 0.9190 0.4186 0.1143 11.00000 0.05 0.59 Q2 1 0.8253 0.5647 0.0484 11.00000 0.05 0.58 Q3 1 0.8035 0.5449 0.1910 11.00000 0.05 0.57 Q4 1 0.7792 0.4040 -0.1219 11.00000 0.05 0.42 ; _shelx_res_checksum 38480 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 F1 F -0.0439(2) 0.34589(19) 0.64266(13) 0.0407(4) Uani 1 1 d . . . . . F2 F 0.02819(19) 0.09854(19) 0.14554(14) 0.0395(4) Uani 1 1 d . . . . . N1 N 0.6189(3) 0.1547(2) 0.53481(16) 0.0262(5) Uani 1 1 d . . . . . N2 N 0.6411(3) 0.3226(2) 0.01890(16) 0.0248(5) Uani 1 1 d . . . . . C1 C 0.6559(3) 0.2474(3) 0.43785(19) 0.0244(5) Uani 1 1 d . . . . . C2 C 0.5125(3) 0.3363(3) 0.41163(19) 0.0228(5) Uani 1 1 d . . . . . C3 C 0.3803(3) 0.2998(2) 0.49795(19) 0.0228(5) Uani 1 1 d . . . . . C4 C 0.2108(3) 0.3553(3) 0.5209(2) 0.0259(5) Uani 1 1 d . . . . . H4A H 0.159517 0.433456 0.473457 0.031 Uiso 1 1 calc R U . . . C5 C 0.1219(3) 0.2911(3) 0.6157(2) 0.0300(6) Uani 1 1 d . . . . . C6 C 0.1871(3) 0.1746(3) 0.6876(2) 0.0318(6) Uani 1 1 d . . . . . H6A H 0.117799 0.133805 0.750566 0.038 Uiso 1 1 calc R U . . . C7 C 0.3553(3) 0.1188(3) 0.6660(2) 0.0294(6) Uani 1 1 d . . . . . H7A H 0.403617 0.038762 0.713163 0.035 Uiso 1 1 calc R U . . . C8 C 0.4511(3) 0.1839(3) 0.5730(2) 0.0247(5) Uani 1 1 d . . . . . C9 C 0.7376(4) 0.0476(3) 0.5915(2) 0.0344(6) Uani 1 1 d . . . . . H9A H 0.849576 0.046528 0.548205 0.052 Uiso 1 1 calc R U . . . H9B H 0.747143 0.077270 0.669888 0.052 Uiso 1 1 calc R U . . . H9C H 0.695980 -0.053058 0.594477 0.052 Uiso 1 1 calc R U . . . C10 C 0.8297(3) 0.2430(3) 0.3777(2) 0.0317(6) Uani 1 1 d . . . . . H10A H 0.904680 0.167563 0.417153 0.047 Uiso 1 1 calc R U . . . H10B H 0.824751 0.216471 0.297949 0.047 Uiso 1 1 calc R U . . . H10C H 0.874356 0.342136 0.378279 0.047 Uiso 1 1 calc R U . . . C11 C 0.4974(3) 0.4514(3) 0.31133(19) 0.0234(5) Uani 1 1 d . . . . . H11A H 0.382627 0.505017 0.318732 0.028 Uiso 1 1 calc R U . . . H11B H 0.581565 0.526486 0.316104 0.028 Uiso 1 1 calc R U . . . C12 C 0.6610(3) 0.4017(3) 0.11440(19) 0.0230(5) Uani 1 1 d . . . . . C13 C 0.5252(3) 0.3861(2) 0.19450(19) 0.0216(5) Uani 1 1 d . . . . . C14 C 0.4130(3) 0.2938(2) 0.14611(19) 0.0208(5) Uani 1 1 d . . . . . C15 C 0.2537(3) 0.2408(3) 0.1840(2) 0.0242(5) Uani 1 1 d . . . . . H15A H 0.197465 0.264660 0.256609 0.029 Uiso 1 1 calc R U . . . C16 C 0.1831(3) 0.1528(3) 0.1110(2) 0.0279(6) Uani 1 1 d . . . . . C17 C 0.2573(3) 0.1156(3) 0.0030(2) 0.0295(6) Uani 1 1 d . . . . . H17A H 0.201550 0.055145 -0.043764 0.035 Uiso 1 1 calc R U . . . C18 C 0.4126(3) 0.1676(3) -0.0353(2) 0.0279(6) Uani 1 1 d . . . . . H18A H 0.466172 0.143836 -0.108654 0.034 Uiso 1 1 calc R U . . . C19 C 0.4894(3) 0.2562(3) 0.03662(19) 0.0232(5) Uani 1 1 d . . . . . C20 C 0.7588(3) 0.3097(3) -0.0841(2) 0.0321(6) Uani 1 1 d . . . . . H20A H 0.857487 0.366775 -0.076380 0.048 Uiso 1 1 calc DR U . . . H20B H 0.796896 0.203561 -0.093515 0.048 Uiso 1 1 calc R U . . . H20C H 0.701092 0.350104 -0.151628 0.048 Uiso 1 1 calc R U . . . C21 C 0.8150(3) 0.4893(3) 0.1180(2) 0.0290(6) Uani 1 1 d . . . . . H21A H 0.888902 0.477286 0.046780 0.043 Uiso 1 1 calc DR U . . . H21B H 0.778586 0.596135 0.125570 0.043 Uiso 1 1 calc R U . . . H21C H 0.877738 0.451615 0.183990 0.043 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 F1 0.0327(9) 0.0492(10) 0.0373(9) 0.0008(7) 0.0081(7) 0.0000(7) F2 0.0322(9) 0.0467(10) 0.0425(9) -0.0029(7) -0.0019(7) -0.0208(7) N1 0.0326(11) 0.0240(10) 0.0226(10) -0.0009(8) -0.0077(8) -0.0004(8) N2 0.0237(10) 0.0289(10) 0.0212(10) -0.0009(8) 0.0007(8) -0.0021(8) C1 0.0306(12) 0.0234(11) 0.0205(11) -0.0043(9) -0.0057(9) -0.0034(9) C2 0.0271(12) 0.0236(11) 0.0187(11) -0.0037(9) -0.0046(9) -0.0046(9) C3 0.0300(12) 0.0202(11) 0.0195(11) -0.0052(9) -0.0052(9) -0.0039(9) C4 0.0285(12) 0.0266(12) 0.0231(12) -0.0017(9) -0.0029(9) -0.0039(10) C5 0.0290(13) 0.0340(14) 0.0273(12) -0.0055(10) 0.0010(10) -0.0041(10) C6 0.0410(15) 0.0344(14) 0.0210(12) -0.0019(10) 0.0005(10) -0.0118(11) C7 0.0431(15) 0.0262(12) 0.0204(11) -0.0015(9) -0.0065(10) -0.0068(10) C8 0.0333(13) 0.0218(11) 0.0206(11) -0.0039(9) -0.0068(9) -0.0056(9) C9 0.0415(15) 0.0312(14) 0.0316(13) 0.0011(11) -0.0151(11) 0.0016(11) C10 0.0275(13) 0.0366(14) 0.0312(13) -0.0043(11) -0.0048(10) 0.0000(10) C11 0.0261(12) 0.0226(11) 0.0222(11) -0.0021(9) -0.0042(9) -0.0030(9) C12 0.0233(11) 0.0214(11) 0.0241(11) 0.0020(9) -0.0049(9) -0.0011(9) C13 0.0227(11) 0.0209(11) 0.0213(11) 0.0006(8) -0.0038(8) -0.0016(9) C14 0.0229(11) 0.0192(11) 0.0201(11) 0.0013(8) -0.0048(9) 0.0007(8) C15 0.0243(12) 0.0264(12) 0.0217(11) 0.0000(9) -0.0019(9) -0.0026(9) C16 0.0235(12) 0.0291(12) 0.0317(13) 0.0040(10) -0.0060(10) -0.0070(10) C17 0.0349(14) 0.0270(12) 0.0286(13) -0.0046(10) -0.0109(10) -0.0044(10) C18 0.0327(13) 0.0297(13) 0.0217(11) -0.0042(9) -0.0051(10) 0.0011(10) C19 0.0239(11) 0.0238(11) 0.0218(11) 0.0013(9) -0.0039(9) 0.0001(9) C20 0.0308(13) 0.0377(14) 0.0260(13) -0.0020(10) 0.0062(10) -0.0010(11) C21 0.0243(12) 0.0299(13) 0.0325(13) 0.0023(10) -0.0017(10) -0.0052(10) 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' F F 0.0727 0.0534 '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' 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 C8 N1 C1 108.88(19) . . ? C8 N1 C9 124.5(2) . . ? C1 N1 C9 126.5(2) . . ? C19 N2 C12 108.40(19) . . ? C19 N2 C20 124.8(2) . . ? C12 N2 C20 126.8(2) . . ? C2 C1 N1 109.8(2) . . ? C2 C1 C10 128.8(2) . . ? N1 C1 C10 121.4(2) . . ? C1 C2 C3 106.7(2) . . ? C1 C2 C11 126.8(2) . . ? C3 C2 C11 126.6(2) . . ? C4 C3 C8 119.1(2) . . ? C4 C3 C2 133.8(2) . . ? C8 C3 C2 107.0(2) . . ? C5 C4 C3 116.8(2) . . ? C5 C4 H4A 121.6 . . ? C3 C4 H4A 121.6 . . ? F1 C5 C4 118.3(2) . . ? F1 C5 C6 116.8(2) . . ? C4 C5 C6 124.9(2) . . ? C7 C6 C5 118.9(2) . . ? C7 C6 H6A 120.5 . . ? C5 C6 H6A 120.5 . . ? C6 C7 C8 117.9(2) . . ? C6 C7 H7A 121.0 . . ? C8 C7 H7A 121.0 . . ? N1 C8 C7 130.1(2) . . ? N1 C8 C3 107.6(2) . . ? C7 C8 C3 122.3(2) . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C13 C11 C2 114.42(19) . . ? C13 C11 H11A 108.7 . . ? C2 C11 H11A 108.7 . . ? C13 C11 H11B 108.7 . . ? C2 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C13 C12 N2 110.1(2) . . ? C13 C12 C21 129.7(2) . . ? N2 C12 C21 120.2(2) . . ? C12 C13 C14 106.5(2) . . ? C12 C13 C11 127.5(2) . . ? C14 C13 C11 126.0(2) . . ? C15 C14 C19 119.0(2) . . ? C15 C14 C13 134.0(2) . . ? C19 C14 C13 107.0(2) . . ? C16 C15 C14 116.9(2) . . ? C16 C15 H15A 121.5 . . ? C14 C15 H15A 121.5 . . ? F2 C16 C15 118.4(2) . . ? F2 C16 C17 117.1(2) . . ? C15 C16 C17 124.5(2) . . ? C18 C17 C16 119.1(2) . . ? C18 C17 H17A 120.4 . . ? C16 C17 H17A 120.4 . . ? C17 C18 C19 118.2(2) . . ? C17 C18 H18A 120.9 . . ? C19 C18 H18A 120.9 . . ? N2 C19 C18 129.8(2) . . ? N2 C19 C14 107.9(2) . . ? C18 C19 C14 122.3(2) . . ? N2 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C12 C21 H21A 109.5 . . ? C12 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C12 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 F1 C5 1.377(3) . ? F2 C16 1.373(3) . ? N1 C8 1.371(3) . ? N1 C1 1.385(3) . ? N1 C9 1.454(3) . ? N2 C19 1.375(3) . ? N2 C12 1.384(3) . ? N2 C20 1.460(3) . ? C1 C2 1.375(3) . ? C1 C10 1.486(3) . ? C2 C3 1.430(3) . ? C2 C11 1.515(3) . ? C3 C4 1.399(3) . ? C3 C8 1.424(3) . ? C4 C5 1.378(3) . ? C4 H4A 0.9500 . ? C5 C6 1.390(4) . ? C6 C7 1.388(4) . ? C6 H6A 0.9500 . ? C7 C8 1.394(3) . ? C7 H7A 0.9500 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C13 1.508(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.371(3) . ? C12 C21 1.506(3) . ? C13 C14 1.433(3) . ? C14 C15 1.408(3) . ? C14 C19 1.413(3) . ? C15 C16 1.376(3) . ? C15 H15A 0.9500 . ? C16 C17 1.392(4) . ? C17 C18 1.377(4) . ? C17 H17A 0.9500 . ? C18 C19 1.397(3) . ? C18 H18A 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 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 C8 N1 C1 C2 -0.6(3) . . . . ? C9 N1 C1 C2 -178.2(2) . . . . ? C8 N1 C1 C10 179.1(2) . . . . ? C9 N1 C1 C10 1.5(4) . . . . ? N1 C1 C2 C3 1.3(2) . . . . ? C10 C1 C2 C3 -178.4(2) . . . . ? N1 C1 C2 C11 -179.1(2) . . . . ? C10 C1 C2 C11 1.3(4) . . . . ? C1 C2 C3 C4 176.8(2) . . . . ? C11 C2 C3 C4 -2.8(4) . . . . ? C1 C2 C3 C8 -1.6(2) . . . . ? C11 C2 C3 C8 178.8(2) . . . . ? C8 C3 C4 C5 -0.8(3) . . . . ? C2 C3 C4 C5 -179.0(2) . . . . ? C3 C4 C5 F1 178.23(19) . . . . ? C3 C4 C5 C6 -1.3(4) . . . . ? F1 C5 C6 C7 -178.0(2) . . . . ? C4 C5 C6 C7 1.6(4) . . . . ? C5 C6 C7 C8 0.5(3) . . . . ? C1 N1 C8 C7 179.3(2) . . . . ? C9 N1 C8 C7 -3.1(4) . . . . ? C1 N1 C8 C3 -0.5(2) . . . . ? C9 N1 C8 C3 177.2(2) . . . . ? C6 C7 C8 N1 177.7(2) . . . . ? C6 C7 C8 C3 -2.6(3) . . . . ? C4 C3 C8 N1 -177.39(19) . . . . ? C2 C3 C8 N1 1.2(2) . . . . ? C4 C3 C8 C7 2.9(3) . . . . ? C2 C3 C8 C7 -178.5(2) . . . . ? C1 C2 C11 C13 63.9(3) . . . . ? C3 C2 C11 C13 -116.5(2) . . . . ? C19 N2 C12 C13 0.7(3) . . . . ? C20 N2 C12 C13 -179.2(2) . . . . ? C19 N2 C12 C21 -178.6(2) . . . . ? C20 N2 C12 C21 1.5(3) . . . . ? N2 C12 C13 C14 -0.7(2) . . . . ? C21 C12 C13 C14 178.5(2) . . . . ? N2 C12 C13 C11 178.9(2) . . . . ? C21 C12 C13 C11 -1.9(4) . . . . ? C2 C11 C13 C12 -109.7(3) . . . . ? C2 C11 C13 C14 69.8(3) . . . . ? C12 C13 C14 C15 -178.4(2) . . . . ? C11 C13 C14 C15 1.9(4) . . . . ? C12 C13 C14 C19 0.5(2) . . . . ? C11 C13 C14 C19 -179.1(2) . . . . ? C19 C14 C15 C16 0.8(3) . . . . ? C13 C14 C15 C16 179.6(2) . . . . ? C14 C15 C16 F2 179.7(2) . . . . ? C14 C15 C16 C17 -1.0(4) . . . . ? F2 C16 C17 C18 180.0(2) . . . . ? C15 C16 C17 C18 0.6(4) . . . . ? C16 C17 C18 C19 0.0(4) . . . . ? C12 N2 C19 C18 178.9(2) . . . . ? C20 N2 C19 C18 -1.2(4) . . . . ? C12 N2 C19 C14 -0.4(2) . . . . ? C20 N2 C19 C14 179.6(2) . . . . ? C17 C18 C19 N2 -179.3(2) . . . . ? C17 C18 C19 C14 -0.1(3) . . . . ? C15 C14 C19 N2 179.04(19) . . . . ? C13 C14 C19 N2 -0.1(2) . . . . ? C15 C14 C19 C18 -0.3(3) . . . . ? C13 C14 C19 C18 -179.4(2) . . . . ?