#------------------------------------------------------------------------------ #$Date: 2023-09-23 00:55:23 +0300 (Sat, 23 Sep 2023) $ #$Revision: 286469 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132147.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_7132147 loop_ _publ_author_name 'Li, Wanwan' 'Gong, Qingbao' 'Wu, Qinghua' 'Guo, Luying' 'Guo, Xing' 'Guo, Dianjun' 'Jiao, Lijuan' 'Hao, Erhong' _publ_section_title ; Pictet--Spengler Synthesis of Twist Quinoline-Fused BODIPYs as Heavy-Atom-Free Photosensitizers ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/D3CC04460B _journal_year 2023 _chemical_formula_moiety 'C30 H23 B F2 N4' _chemical_formula_sum 'C30 H23 B F2 N4' _chemical_formula_weight 488.33 _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 2023-09-15 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2023-09-15 deposited with the CCDC. 2023-09-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.146(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.348(4) _cell_length_b 18.253(6) _cell_length_c 11.465(4) _cell_measurement_reflns_used 556 _cell_measurement_temperature 300.00 _cell_measurement_theta_max 24.862 _cell_measurement_theta_min 2.371 _cell_volume 2426.0(14) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_collection 'Bruker SMART APEX II diffractometer' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/2 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 300.00 _diffrn_detector 'CCD area detector' _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0722 _diffrn_reflns_av_unetI/netI 0.0617 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 17303 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.201 _diffrn_reflns_theta_max 25.201 _diffrn_reflns_theta_min 2.081 _diffrn_source 'sealed X-ray tube' _diffrn_source_target Mo _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.5189 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1745 before and 0.0637 after correction. The Ratio of minimum to maximum transmission is 0.6963. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'metallic dark black' _exptl_crystal_colour_lustre metallic _exptl_crystal_colour_modifier dark _exptl_crystal_colour_primary black _exptl_crystal_density_diffrn 1.337 _exptl_crystal_description block _exptl_crystal_F_000 1016 _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.189 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 383 _refine_ls_number_reflns 4347 _refine_ls_number_restraints 236 _refine_ls_restrained_S_all 1.013 _refine_ls_R_factor_all 0.0952 _refine_ls_R_factor_gt 0.0496 _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^)+(0.0676P)^2^+0.2520P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1178 _refine_ls_wR_factor_ref 0.1389 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2751 _reflns_number_total 4347 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3cc04460b2.cif _cod_data_source_block 3c _cod_original_cell_volume 2425.9(14) _cod_database_code 7132147 _shelx_shelxl_version_number 2019/2 _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 0.982 _shelx_estimated_absorpt_t_min 0.980 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Restrained distances N4A-C17 \\sim N4-C17 with sigma of 0.02 N4A-C21A \\sim N4-C21 with sigma of 0.02 C18-C17 \\sim C18A-C17 with sigma of 0.02 3. Restrained planarity C21A, C17, C18A, C20A, N4A, C19A with sigma of 0.1 C21, C17, C18, C20, N4, C19 with sigma of 0.1 4. Uiso/Uaniso restraints and constraints N4 \\sim C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim N4A \\sim C18A \\sim C19A \\sim C20A \\sim C21A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A 5. Rigid body (RIGU) restrains N4, C17, C18, C19, C20, C21, N4A, C18A, C19A, C20A, C21A with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02 6. Same fragment restrains {C18A, C19A, C20A, C21A} sigma for 1-2: 0.02, 1-3: 0.02 as in {C18, C19, C20, C21} 7. Others Sof(N4A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)= Sof(C21A)=Sof(H21A)=1-FVAR(1) Sof(N4)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)= Sof(H21)=FVAR(1) 8.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C7(H7), C11(H11), C12(H12), C13(H13), C14(H14), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C26(H26), C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A) 8.b Idealised Me refined as rotating group: C28(H28A,H28B,H28C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C) ; _shelx_res_file ; TITL 3a_a.res in P2(1)/c 3c.res created by SHELXL-2019/2 at 17:07:58 on 15-Sep-2023 REM Old TITL 3a in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.187, Rweak 0.016, Alpha 0.036 REM 0.557 for 159 systematic absences, Orientation as input REM Formula found by SHELXT: C32 N3 F2 CELL 0.71073 12.348 18.2531 11.4646 90 110.146 90 ZERR 4 0.0041 0.0058 0.0036 0 0.009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H B F N UNIT 120 92 4 8 16 SADI 0.02 N4A C17 N4 C17 FLAT 0.1 C21A C17 C18A C20A N4A C19A RIGU 0.01 0.02 N4 C17 C18 C19 C20 C21 N4A C18A C19A C20A C21A SADI 0.02 N4A C21A N4 C21 SIMU 0.01 0.02 2 N4 C17 C18 C19 C20 C21 N4A C18A C19A C20A C21A SADI 0.02 C18 C17 C18A C17 FLAT 0.1 C21 C17 C18 C20 N4 C19 L.S. 10 PLAN 1 SIZE 0.2 0.21 0.22 TEMP 20 CONF BOND list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.067600 0.252000 FVAR 0.42485 0.44583 F1 4 0.665235 0.564634 0.780484 11.00000 0.04628 0.05281 = 0.05971 -0.00298 0.01353 -0.00674 F2 4 0.619350 0.531029 0.579903 11.00000 0.06111 0.05090 = 0.06283 0.00180 0.04445 0.00140 N1 5 0.541266 0.461052 0.708666 11.00000 0.03800 0.03926 = 0.04155 0.00114 0.02190 0.00201 N2 5 0.469438 0.586923 0.641809 11.00000 0.03857 0.03552 = 0.04207 0.00072 0.02292 -0.00185 N3 5 0.355462 0.777135 0.437404 11.00000 0.05434 0.04399 = 0.04986 0.00573 0.02214 -0.00076 PART 1 N4 5 0.092017 0.727564 0.485737 21.00000 0.04173 0.06506 = 0.08728 0.02195 0.01982 0.00759 PART 0 C1 1 0.604255 0.400185 0.729900 11.00000 0.04219 0.04502 = 0.04894 -0.00001 0.02343 0.00641 AFIX 43 H1 2 0.677071 0.396343 0.723417 11.00000 -1.20000 AFIX 0 C2 1 0.545677 0.342532 0.763450 11.00000 0.05720 0.03949 = 0.05203 0.00488 0.02384 0.00703 AFIX 43 H2 2 0.572152 0.294785 0.782478 11.00000 -1.20000 AFIX 0 C3 1 0.442898 0.369650 0.762891 11.00000 0.05246 0.04278 = 0.04942 0.00543 0.02553 -0.00272 AFIX 43 H3 2 0.386140 0.343923 0.781946 11.00000 -1.20000 AFIX 0 C4 1 0.438292 0.444684 0.727747 11.00000 0.04134 0.03944 = 0.04150 0.00161 0.02329 -0.00121 C5 1 0.352110 0.495696 0.704409 11.00000 0.03966 0.03993 = 0.03483 -0.00109 0.01987 -0.00616 C6 1 0.364856 0.565299 0.653966 11.00000 0.03642 0.03614 = 0.03945 -0.00248 0.02164 -0.00196 C7 1 0.280914 0.617352 0.602594 11.00000 0.03807 0.04109 = 0.04641 -0.00324 0.02250 -0.00212 AFIX 43 H7 2 0.205145 0.616152 0.601075 11.00000 -1.20000 AFIX 0 C8 1 0.331684 0.672603 0.552929 11.00000 0.04573 0.03472 = 0.04151 -0.00256 0.02071 -0.00282 C9 1 0.287983 0.736562 0.478224 11.00000 0.05019 0.03781 = 0.04699 -0.00125 0.01947 -0.00083 C10 1 0.471620 0.762166 0.475148 11.00000 0.05293 0.04245 = 0.04771 -0.00185 0.02841 -0.00270 C11 1 0.539393 0.812075 0.437327 11.00000 0.06760 0.04469 = 0.06609 0.01228 0.04086 0.00103 AFIX 43 H11 2 0.503979 0.849881 0.383263 11.00000 -1.20000 AFIX 0 C12 1 0.656416 0.805805 0.478856 11.00000 0.08029 0.04792 = 0.09760 0.01225 0.06295 -0.00203 AFIX 43 H12 2 0.700003 0.839321 0.452711 11.00000 -1.20000 AFIX 0 C13 1 0.712068 0.749286 0.560751 11.00000 0.05292 0.05134 = 0.11263 0.01093 0.05252 0.00278 AFIX 43 H13 2 0.792174 0.746863 0.592554 11.00000 -1.20000 AFIX 0 C14 1 0.646264 0.697333 0.593453 11.00000 0.05307 0.04167 = 0.07635 0.00459 0.03765 -0.00156 AFIX 43 H14 2 0.682858 0.658526 0.644361 11.00000 -1.20000 AFIX 0 C15 1 0.526289 0.701805 0.551834 11.00000 0.04462 0.03974 = 0.04739 -0.00311 0.02558 -0.00267 C16 1 0.448944 0.652894 0.582123 11.00000 0.04390 0.03579 = 0.03896 -0.00220 0.02144 -0.00207 C17 1 0.166343 0.761085 0.442542 11.00000 0.05188 0.04593 = 0.05880 0.00383 0.01918 0.00283 SAME 0.02 0.02 C18A C19A C20A C21A PART 1 C18 1 0.129360 0.821055 0.362044 21.00000 0.05901 0.07321 = 0.07375 0.01941 0.00671 0.00203 AFIX 43 H18 2 0.180250 0.844061 0.330020 21.00000 -1.20000 AFIX 0 C19 1 0.017952 0.845710 0.330639 21.00000 0.06279 0.07396 = 0.08919 0.01870 0.00525 0.01260 AFIX 43 H19 2 -0.004989 0.888340 0.284240 21.00000 -1.20000 AFIX 0 C20 1 -0.059589 0.806702 0.368505 21.00000 0.05263 0.09529 = 0.08997 0.01341 0.00963 0.01381 AFIX 43 H20 2 -0.137625 0.818518 0.339807 21.00000 -1.20000 AFIX 0 C21 1 -0.018253 0.750351 0.449229 21.00000 0.04556 0.08504 = 0.09987 0.01653 0.02184 0.01027 AFIX 43 H21 2 -0.068703 0.726391 0.480742 21.00000 -1.20000 AFIX 0 PART 0 C22 1 0.242030 0.477884 0.725965 11.00000 0.03601 0.03595 = 0.04939 0.00257 0.02296 -0.00202 C23 1 0.149665 0.446732 0.631423 11.00000 0.04530 0.05555 = 0.05444 -0.00776 0.02235 -0.00869 C24 1 0.050201 0.430371 0.656380 11.00000 0.04560 0.08061 = 0.07133 -0.01475 0.02168 -0.02159 AFIX 43 H24 2 -0.011578 0.409569 0.593699 11.00000 -1.20000 AFIX 0 C25 1 0.038807 0.443535 0.769745 11.00000 0.04922 0.07231 = 0.07960 -0.00010 0.03832 -0.01089 C26 1 0.131620 0.473705 0.861620 11.00000 0.06138 0.07340 = 0.06007 -0.00224 0.04139 -0.00628 AFIX 43 H26 2 0.125639 0.482610 0.939042 11.00000 -1.20000 AFIX 0 C27 1 0.233804 0.491331 0.843013 11.00000 0.04574 0.05032 = 0.04667 -0.00181 0.02550 -0.00624 C28 1 0.157620 0.429852 0.506230 11.00000 0.06301 0.09998 = 0.05872 -0.02406 0.02552 -0.01393 AFIX 137 H28A 2 0.187181 0.471804 0.476491 11.00000 -1.50000 H28B 2 0.082353 0.418013 0.448912 11.00000 -1.50000 H28C 2 0.208403 0.388963 0.513372 11.00000 -1.50000 AFIX 0 C29 1 -0.073482 0.426258 0.790539 11.00000 0.05937 0.15168 = 0.11996 -0.00021 0.05528 -0.02662 AFIX 137 H29A 2 -0.130406 0.462294 0.749251 11.00000 -1.50000 H29B 2 -0.060933 0.426944 0.877956 11.00000 -1.50000 H29C 2 -0.100088 0.378616 0.757554 11.00000 -1.50000 AFIX 0 C30 1 0.332934 0.523520 0.947195 11.00000 0.06578 0.08819 = 0.05428 -0.01300 0.03028 -0.01732 AFIX 137 H30A 2 0.399973 0.493269 0.962214 11.00000 -1.50000 H30B 2 0.313148 0.525881 1.021079 11.00000 -1.50000 H30C 2 0.348941 0.571950 0.924776 11.00000 -1.50000 AFIX 0 B1 3 0.578260 0.537871 0.676737 11.00000 0.03993 0.03931 = 0.04131 -0.00378 0.02201 -0.00544 PART 2 N4A 5 0.115789 0.740492 0.524527 -21.00000 0.04664 0.06794 = 0.08137 0.01167 0.02601 0.01128 C18A 1 0.114641 0.804805 0.340313 -21.00000 0.06537 0.07684 = 0.06743 0.01843 0.01644 0.00509 AFIX 43 H18A 2 0.154435 0.818262 0.287976 -21.00000 -1.20000 AFIX 0 C19A 1 0.003319 0.828159 0.317066 -21.00000 0.06075 0.08986 = 0.08989 0.02808 0.00376 0.01527 AFIX 43 H19A 2 -0.035761 0.854508 0.245482 -21.00000 -1.20000 AFIX 0 C20A 1 -0.049080 0.811587 0.402438 -21.00000 0.05158 0.09476 = 0.09815 0.01625 0.01915 0.02150 AFIX 43 H20A 2 -0.121106 0.830681 0.394480 -21.00000 -1.20000 AFIX 0 C21A 1 0.007916 0.766314 0.499003 -21.00000 0.05007 0.08529 = 0.09114 0.01233 0.02383 0.01151 AFIX 43 H21A 2 -0.031161 0.752107 0.551644 -21.00000 -1.20000 AFIX 0 HKLF 4 REM 3a_a.res in P2(1)/c REM wR2 = 0.1389, GooF = S = 1.022, Restrained GooF = 1.013 for all data REM R1 = 0.0496 for 2751 Fo > 4sig(Fo) and 0.0952 for all 4347 data REM 383 parameters refined using 236 restraints END WGHT 0.0676 0.2520 REM Highest difference peak 0.189, deepest hole -0.241, 1-sigma level 0.045 Q1 1 0.4013 0.5512 0.9290 11.00000 0.05 0.19 ; _shelx_res_checksum 94172 _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 F1 F 0.66523(12) 0.56463(7) 0.78048(12) 0.0542(4) Uani 1 1 d . . . . . F2 F 0.61935(13) 0.53103(7) 0.57990(12) 0.0523(4) Uani 1 1 d . . . . . N1 N 0.54127(17) 0.46105(9) 0.70867(15) 0.0375(5) Uani 1 1 d . . . . . N2 N 0.46944(16) 0.58692(9) 0.64181(15) 0.0364(5) Uani 1 1 d . . . . . N3 N 0.3555(2) 0.77713(10) 0.43740(17) 0.0483(5) Uani 1 1 d . . . . . N4 N 0.0920(10) 0.7276(7) 0.4857(12) 0.065(2) Uani 0.446(18) 1 d D U P A 1 C1 C 0.6043(2) 0.40018(12) 0.7299(2) 0.0434(6) Uani 1 1 d . . . . . H1 H 0.677071 0.396343 0.723417 0.052 Uiso 1 1 calc R U . . . C2 C 0.5457(2) 0.34253(13) 0.7635(2) 0.0483(6) Uani 1 1 d . . . . . H2 H 0.572152 0.294785 0.782478 0.058 Uiso 1 1 calc R U . . . C3 C 0.4429(2) 0.36965(12) 0.7629(2) 0.0461(6) Uani 1 1 d . . . . . H3 H 0.386140 0.343923 0.781946 0.055 Uiso 1 1 calc R U . . . C4 C 0.4383(2) 0.44468(12) 0.72775(19) 0.0384(6) Uani 1 1 d . . . . . C5 C 0.3521(2) 0.49570(12) 0.70441(18) 0.0363(5) Uani 1 1 d . . . . . C6 C 0.3649(2) 0.56530(11) 0.65397(18) 0.0351(5) Uani 1 1 d . . . . . C7 C 0.2809(2) 0.61735(11) 0.60259(19) 0.0398(6) Uani 1 1 d . . . . . H7 H 0.205145 0.616152 0.601075 0.048 Uiso 1 1 calc R U . . . C8 C 0.3317(2) 0.67260(11) 0.55293(19) 0.0392(6) Uani 1 1 d . . . . . C9 C 0.2880(2) 0.73656(12) 0.4782(2) 0.0443(6) Uani 1 1 d . . . . . C10 C 0.4716(2) 0.76217(12) 0.4751(2) 0.0448(6) Uani 1 1 d . . . . . C11 C 0.5394(3) 0.81208(13) 0.4373(2) 0.0548(7) Uani 1 1 d . . . . . H11 H 0.503979 0.849881 0.383263 0.066 Uiso 1 1 calc R U . . . C12 C 0.6564(3) 0.80581(14) 0.4789(3) 0.0669(9) Uani 1 1 d . . . . . H12 H 0.700003 0.839321 0.452711 0.080 Uiso 1 1 calc R U . . . C13 C 0.7121(3) 0.74929(14) 0.5608(3) 0.0660(8) Uani 1 1 d . . . . . H13 H 0.792174 0.746863 0.592554 0.079 Uiso 1 1 calc R U . . . C14 C 0.6463(2) 0.69733(13) 0.5935(2) 0.0530(7) Uani 1 1 d . . . . . H14 H 0.682858 0.658526 0.644361 0.064 Uiso 1 1 calc R U . . . C15 C 0.5263(2) 0.70180(11) 0.5518(2) 0.0414(6) Uani 1 1 d . . . . . C16 C 0.4489(2) 0.65289(11) 0.58212(18) 0.0377(6) Uani 1 1 d . . . . . C17 C 0.1663(2) 0.76108(13) 0.4425(2) 0.0522(6) Uani 1 1 d D U . . . C18 C 0.1294(12) 0.8211(7) 0.3620(12) 0.073(3) Uani 0.446(18) 1 d D U P A 1 H18 H 0.180250 0.844061 0.330020 0.087 Uiso 0.446(18) 1 calc R U P A 1 C19 C 0.0180(13) 0.8457(8) 0.3306(14) 0.081(3) Uani 0.446(18) 1 d D U P A 1 H19 H -0.004989 0.888340 0.284240 0.097 Uiso 0.446(18) 1 calc R U P A 1 C20 C -0.0596(13) 0.8067(9) 0.3685(13) 0.083(3) Uani 0.446(18) 1 d D U P A 1 H20 H -0.137625 0.818518 0.339807 0.100 Uiso 0.446(18) 1 calc R U P A 1 C21 C -0.0183(11) 0.7504(7) 0.4492(14) 0.078(2) Uani 0.446(18) 1 d D U P A 1 H21 H -0.068703 0.726391 0.480742 0.093 Uiso 0.446(18) 1 calc R U P A 1 C22 C 0.2420(2) 0.47788(11) 0.7260(2) 0.0383(6) Uani 1 1 d . . . . . C23 C 0.1497(2) 0.44673(13) 0.6314(2) 0.0504(7) Uani 1 1 d . . . . . C24 C 0.0502(3) 0.43037(15) 0.6564(3) 0.0654(8) Uani 1 1 d . . . . . H24 H -0.011578 0.409569 0.593699 0.079 Uiso 1 1 calc R U . . . C25 C 0.0388(3) 0.44353(15) 0.7697(3) 0.0628(8) Uani 1 1 d . . . . . C26 C 0.1316(3) 0.47370(14) 0.8616(2) 0.0596(8) Uani 1 1 d . . . . . H26 H 0.125639 0.482610 0.939042 0.072 Uiso 1 1 calc R U . . . C27 C 0.2338(2) 0.49133(13) 0.8430(2) 0.0451(6) Uani 1 1 d . . . . . C28 C 0.1576(3) 0.42985(17) 0.5062(2) 0.0727(9) Uani 1 1 d . . . . . H28A H 0.187181 0.471804 0.476491 0.109 Uiso 1 1 calc R U . . . H28B H 0.082353 0.418013 0.448912 0.109 Uiso 1 1 calc R U . . . H28C H 0.208403 0.388963 0.513372 0.109 Uiso 1 1 calc R U . . . C29 C -0.0735(3) 0.4263(2) 0.7905(4) 0.1040(13) Uani 1 1 d . . . . . H29A H -0.130406 0.462294 0.749251 0.156 Uiso 1 1 calc R U . . . H29B H -0.060933 0.426944 0.877956 0.156 Uiso 1 1 calc R U . . . H29C H -0.100088 0.378616 0.757554 0.156 Uiso 1 1 calc R U . . . C30 C 0.3329(3) 0.52352(16) 0.9472(2) 0.0669(8) Uani 1 1 d . . . . . H30A H 0.399973 0.493269 0.962214 0.100 Uiso 1 1 calc R U . . . H30B H 0.313148 0.525881 1.021079 0.100 Uiso 1 1 calc R U . . . H30C H 0.348941 0.571950 0.924776 0.100 Uiso 1 1 calc R U . . . B1 B 0.5783(3) 0.53787(13) 0.6767(2) 0.0381(6) Uani 1 1 d . . . . . N4A N 0.1158(9) 0.7405(6) 0.5245(9) 0.0643(19) Uani 0.554(18) 1 d D U P A 2 C18A C 0.1146(10) 0.8048(6) 0.3403(9) 0.072(2) Uani 0.554(18) 1 d D U P A 2 H18A H 0.154435 0.818262 0.287976 0.086 Uiso 0.554(18) 1 calc R U P A 2 C19A C 0.0033(11) 0.8282(7) 0.3171(11) 0.086(2) Uani 0.554(18) 1 d D U P A 2 H19A H -0.035761 0.854508 0.245482 0.103 Uiso 0.554(18) 1 calc R U P A 2 C20A C -0.0491(10) 0.8116(7) 0.4024(11) 0.083(2) Uani 0.554(18) 1 d D U P A 2 H20A H -0.121106 0.830681 0.394480 0.100 Uiso 0.554(18) 1 calc R U P A 2 C21A C 0.0079(9) 0.7663(6) 0.4990(11) 0.076(2) Uani 0.554(18) 1 d D U P A 2 H21A H -0.031161 0.752107 0.551644 0.091 Uiso 0.554(18) 1 calc R U P A 2 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 0.0463(10) 0.0528(8) 0.0597(8) -0.0030(7) 0.0135(7) -0.0067(7) F2 0.0611(11) 0.0509(8) 0.0628(8) 0.0018(6) 0.0444(8) 0.0014(7) N1 0.0380(13) 0.0393(10) 0.0415(10) 0.0011(8) 0.0219(9) 0.0020(9) N2 0.0386(13) 0.0355(10) 0.0421(10) 0.0007(8) 0.0229(9) -0.0019(9) N3 0.0543(16) 0.0440(11) 0.0499(11) 0.0057(9) 0.0221(11) -0.0008(10) N4 0.042(4) 0.065(4) 0.087(5) 0.022(4) 0.020(4) 0.008(3) C1 0.0422(17) 0.0450(14) 0.0489(13) 0.0000(10) 0.0234(12) 0.0064(12) C2 0.0572(19) 0.0395(13) 0.0520(13) 0.0049(10) 0.0238(13) 0.0070(13) C3 0.0525(19) 0.0428(13) 0.0494(13) 0.0054(10) 0.0255(13) -0.0027(12) C4 0.0413(16) 0.0394(12) 0.0415(11) 0.0016(9) 0.0233(11) -0.0012(11) C5 0.0397(16) 0.0399(12) 0.0348(11) -0.0011(9) 0.0199(11) -0.0062(11) C6 0.0364(15) 0.0361(11) 0.0394(11) -0.0025(9) 0.0216(11) -0.0020(11) C7 0.0381(16) 0.0411(13) 0.0464(12) -0.0032(10) 0.0225(12) -0.0021(11) C8 0.0457(17) 0.0347(12) 0.0415(12) -0.0026(9) 0.0207(12) -0.0028(11) C9 0.0502(18) 0.0378(13) 0.0470(13) -0.0013(10) 0.0195(13) -0.0008(12) C10 0.0529(19) 0.0424(13) 0.0477(13) -0.0018(10) 0.0284(14) -0.0027(12) C11 0.068(2) 0.0447(14) 0.0661(16) 0.0123(12) 0.0409(16) 0.0010(14) C12 0.080(3) 0.0479(16) 0.098(2) 0.0122(14) 0.063(2) -0.0020(16) C13 0.053(2) 0.0513(16) 0.113(2) 0.0109(16) 0.0525(19) 0.0028(14) C14 0.053(2) 0.0417(14) 0.0764(17) 0.0046(12) 0.0376(16) -0.0016(13) C15 0.0446(18) 0.0397(13) 0.0474(13) -0.0031(10) 0.0256(12) -0.0027(12) C16 0.0439(17) 0.0358(12) 0.0390(12) -0.0022(9) 0.0214(12) -0.0021(11) C17 0.0519(18) 0.0459(14) 0.0588(14) 0.0038(11) 0.0192(13) 0.0028(13) C18 0.059(4) 0.073(5) 0.074(4) 0.019(4) 0.007(4) 0.002(4) C19 0.063(4) 0.074(4) 0.089(4) 0.019(4) 0.005(4) 0.013(4) C20 0.053(4) 0.095(4) 0.090(5) 0.013(4) 0.010(4) 0.014(4) C21 0.046(4) 0.085(4) 0.100(5) 0.017(4) 0.022(4) 0.010(3) C22 0.0360(16) 0.0360(12) 0.0494(12) 0.0026(9) 0.0230(12) -0.0020(10) C23 0.0453(18) 0.0556(15) 0.0544(14) -0.0078(12) 0.0223(13) -0.0087(13) C24 0.046(2) 0.081(2) 0.0713(17) -0.0147(15) 0.0217(16) -0.0216(15) C25 0.049(2) 0.0723(18) 0.0796(18) -0.0001(15) 0.0383(17) -0.0109(15) C26 0.061(2) 0.0734(18) 0.0601(16) -0.0022(13) 0.0414(16) -0.0063(16) C27 0.0457(18) 0.0503(14) 0.0467(13) -0.0018(11) 0.0255(13) -0.0062(12) C28 0.063(2) 0.100(2) 0.0587(16) -0.0241(16) 0.0255(16) -0.0139(18) C29 0.059(3) 0.152(3) 0.120(3) 0.000(3) 0.055(2) -0.027(2) C30 0.066(2) 0.088(2) 0.0543(15) -0.0130(14) 0.0303(16) -0.0173(17) B1 0.0399(19) 0.0393(14) 0.0413(14) -0.0038(11) 0.0220(14) -0.0054(13) N4A 0.047(4) 0.068(4) 0.081(4) 0.012(3) 0.026(3) 0.011(3) C18A 0.065(4) 0.077(4) 0.067(4) 0.018(3) 0.016(3) 0.005(3) C19A 0.061(4) 0.090(5) 0.090(4) 0.028(4) 0.004(3) 0.015(4) C20A 0.052(3) 0.095(4) 0.098(4) 0.016(4) 0.019(3) 0.021(3) C21A 0.050(4) 0.085(4) 0.091(4) 0.012(4) 0.024(4) 0.012(3) 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' B B 0.0013 0.0007 '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 C1 N1 C4 107.44(18) . . ? C1 N1 B1 126.5(2) . . ? C4 N1 B1 125.94(19) . . ? C6 N2 B1 123.95(17) . . ? C16 N2 C6 106.26(18) . . ? C16 N2 B1 129.38(18) . . ? C9 N3 C10 119.7(2) . . ? C17 N4 C21 119.7(9) . . ? N1 C1 H1 124.7 . . ? N1 C1 C2 110.6(2) . . ? C2 C1 H1 124.7 . . ? C1 C2 H2 126.5 . . ? C3 C2 C1 107.1(2) . . ? C3 C2 H2 126.5 . . ? C2 C3 H3 126.3 . . ? C2 C3 C4 107.3(2) . . ? C4 C3 H3 126.3 . . ? N1 C4 C3 107.5(2) . . ? C5 C4 N1 120.85(19) . . ? C5 C4 C3 131.5(2) . . ? C4 C5 C6 119.9(2) . . ? C4 C5 C22 120.55(19) . . ? C6 C5 C22 119.5(2) . . ? N2 C6 C5 121.7(2) . . ? C7 C6 N2 110.23(18) . . ? C7 C6 C5 127.9(2) . . ? C6 C7 H7 126.5 . . ? C6 C7 C8 107.0(2) . . ? C8 C7 H7 126.5 . . ? C7 C8 C9 134.0(2) . . ? C7 C8 C16 106.5(2) . . ? C16 C8 C9 119.4(2) . . ? N3 C9 C8 121.0(2) . . ? N3 C9 C17 115.9(2) . . ? C8 C9 C17 123.1(2) . . ? N3 C10 C11 116.2(2) . . ? N3 C10 C15 124.6(2) . . ? C11 C10 C15 119.1(3) . . ? C10 C11 H11 119.6 . . ? C12 C11 C10 120.8(2) . . ? C12 C11 H11 119.6 . . ? C11 C12 H12 119.6 . . ? C11 C12 C13 120.8(2) . . ? C13 C12 H12 119.6 . . ? C12 C13 H13 120.4 . . ? C14 C13 C12 119.2(3) . . ? C14 C13 H13 120.4 . . ? C13 C14 H14 119.3 . . ? C13 C14 C15 121.5(3) . . ? C15 C14 H14 119.3 . . ? C10 C15 C16 114.6(2) . . ? C14 C15 C10 118.6(2) . . ? C14 C15 C16 126.8(2) . . ? N2 C16 C8 109.92(19) . . ? N2 C16 C15 130.3(2) . . ? C8 C16 C15 119.8(2) . . ? N4 C17 C9 121.4(6) . . ? N4 C17 C18 119.5(9) . . ? C18 C17 C9 119.1(7) . . ? N4A C17 C9 113.0(5) . . ? N4A C17 C18A 124.3(7) . . ? C18A C17 C9 122.5(6) . . ? C17 C18 H18 120.1 . . ? C19 C18 C17 119.9(11) . . ? C19 C18 H18 120.1 . . ? C18 C19 H19 120.3 . . ? C18 C19 C20 119.4(10) . . ? C20 C19 H19 120.3 . . ? C19 C20 H20 121.1 . . ? C21 C20 C19 117.8(10) . . ? C21 C20 H20 121.1 . . ? N4 C21 C20 123.2(11) . . ? N4 C21 H21 118.4 . . ? C20 C21 H21 118.4 . . ? C23 C22 C5 120.36(18) . . ? C23 C22 C27 120.4(2) . . ? C27 C22 C5 119.3(2) . . ? C22 C23 C28 121.3(2) . . ? C24 C23 C22 118.2(2) . . ? C24 C23 C28 120.4(2) . . ? C23 C24 H24 118.5 . . ? C25 C24 C23 122.9(3) . . ? C25 C24 H24 118.5 . . ? C24 C25 C26 117.6(2) . . ? C24 C25 C29 120.5(3) . . ? C26 C25 C29 121.8(3) . . ? C25 C26 H26 118.8 . . ? C25 C26 C27 122.4(2) . . ? C27 C26 H26 118.8 . . ? C22 C27 C30 121.4(2) . . ? C26 C27 C22 118.4(2) . . ? C26 C27 C30 120.2(2) . . ? C23 C28 H28A 109.5 . . ? C23 C28 H28B 109.5 . . ? C23 C28 H28C 109.5 . . ? H28A C28 H28B 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C25 C29 H29A 109.5 . . ? C25 C29 H29B 109.5 . . ? C25 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C27 C30 H30A 109.5 . . ? C27 C30 H30B 109.5 . . ? C27 C30 H30C 109.5 . . ? H30A C30 H30B 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? F1 B1 N1 108.58(19) . . ? F1 B1 N2 111.38(18) . . ? F2 B1 F1 109.4(2) . . ? F2 B1 N1 109.12(17) . . ? F2 B1 N2 111.85(19) . . ? N2 B1 N1 106.43(19) . . ? C21A N4A C17 114.3(7) . . ? C17 C18A H18A 120.5 . . ? C19A C18A C17 118.9(9) . . ? C19A C18A H18A 120.5 . . ? C18A C19A H19A 120.8 . . ? C18A C19A C20A 118.4(8) . . ? C20A C19A H19A 120.8 . . ? C19A C20A H20A 121.0 . . ? C21A C20A C19A 118.1(8) . . ? C21A C20A H20A 121.0 . . ? N4A C21A C20A 125.6(8) . . ? N4A C21A H21A 117.2 . . ? C20A C21A H21A 117.2 . . ? 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 F1 B1 1.388(3) . ? F2 B1 1.376(3) . ? N1 C1 1.330(3) . ? N1 C4 1.395(3) . ? N1 B1 1.557(3) . ? N2 C6 1.402(3) . ? N2 C16 1.365(3) . ? N2 B1 1.548(3) . ? N3 C9 1.315(3) . ? N3 C10 1.375(3) . ? N4 C17 1.332(10) . ? N4 C21 1.345(10) . ? C1 H1 0.9300 . ? C1 C2 1.404(3) . ? C2 H2 0.9300 . ? C2 C3 1.360(3) . ? C3 H3 0.9300 . ? C3 C4 1.423(3) . ? C4 C5 1.369(3) . ? C5 C6 1.427(3) . ? C5 C22 1.499(3) . ? C6 C7 1.380(3) . ? C7 H7 0.9300 . ? C7 C8 1.407(3) . ? C8 C9 1.439(3) . ? C8 C16 1.416(3) . ? C9 C17 1.483(4) . ? C10 C11 1.403(3) . ? C10 C15 1.426(3) . ? C11 H11 0.9300 . ? C11 C12 1.362(4) . ? C12 H12 0.9300 . ? C12 C13 1.405(4) . ? C13 H13 0.9300 . ? C13 C14 1.382(3) . ? C14 H14 0.9300 . ? C14 C15 1.394(4) . ? C15 C16 1.435(3) . ? C17 C18 1.403(11) . ? C17 N4A 1.349(8) . ? C17 C18A 1.379(9) . ? C18 H18 0.9300 . ? C18 C19 1.372(11) . ? C19 H19 0.9300 . ? C19 C20 1.378(12) . ? C20 H20 0.9300 . ? C20 C21 1.360(11) . ? C21 H21 0.9300 . ? C22 C23 1.395(3) . ? C22 C27 1.402(3) . ? C23 C24 1.386(4) . ? C23 C28 1.504(3) . ? C24 H24 0.9300 . ? C24 C25 1.376(4) . ? C25 C26 1.376(4) . ? C25 C29 1.519(4) . ? C26 H26 0.9300 . ? C26 C27 1.388(3) . ? C27 C30 1.504(4) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? N4A C21A 1.347(8) . ? C18A H18A 0.9300 . ? C18A C19A 1.375(9) . ? C19A H19A 0.9300 . ? C19A C20A 1.380(10) . ? C20A H20A 0.9300 . ? C20A C21A 1.366(9) . ? C21A H21A 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 N1 C1 C2 C3 -0.2(3) . . . . ? N1 C4 C5 C6 3.2(3) . . . . ? N1 C4 C5 C22 -179.58(18) . . . . ? N2 C6 C7 C8 1.8(2) . . . . ? N3 C9 C17 N4 -175.1(7) . . . . ? N3 C9 C17 C18 4.6(7) . . . . ? N3 C9 C17 N4A -152.7(6) . . . . ? N3 C9 C17 C18A 23.0(7) . . . . ? N3 C10 C11 C12 174.1(2) . . . . ? N3 C10 C15 C14 -173.5(2) . . . . ? N3 C10 C15 C16 3.9(3) . . . . ? N4 C17 C18 C19 1.4(11) . . . . ? C1 N1 C4 C3 0.3(2) . . . . ? C1 N1 C4 C5 -175.5(2) . . . . ? C1 N1 B1 F1 -68.1(3) . . . . ? C1 N1 B1 F2 51.0(3) . . . . ? C1 N1 B1 N2 171.85(18) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 N1 -0.5(3) . . . . ? C2 C3 C4 C5 174.8(2) . . . . ? C3 C4 C5 C6 -171.5(2) . . . . ? C3 C4 C5 C22 5.7(4) . . . . ? C4 N1 C1 C2 -0.1(3) . . . . ? C4 N1 B1 F1 107.6(2) . . . . ? C4 N1 B1 F2 -133.3(2) . . . . ? C4 N1 B1 N2 -12.4(3) . . . . ? C4 C5 C6 N2 -8.2(3) . . . . ? C4 C5 C6 C7 166.3(2) . . . . ? C4 C5 C22 C23 -89.2(3) . . . . ? C4 C5 C22 C27 89.3(3) . . . . ? C5 C6 C7 C8 -173.25(19) . . . . ? C5 C22 C23 C24 179.2(2) . . . . ? C5 C22 C23 C28 0.3(4) . . . . ? C5 C22 C27 C26 -179.3(2) . . . . ? C5 C22 C27 C30 0.2(3) . . . . ? C6 N2 C16 C8 -1.7(2) . . . . ? C6 N2 C16 C15 176.0(2) . . . . ? C6 N2 B1 F1 -111.1(2) . . . . ? C6 N2 B1 F2 126.2(2) . . . . ? C6 N2 B1 N1 7.1(3) . . . . ? C6 C5 C22 C23 88.0(3) . . . . ? C6 C5 C22 C27 -93.4(2) . . . . ? C6 C7 C8 C9 172.8(2) . . . . ? C6 C7 C8 C16 -2.7(2) . . . . ? C7 C8 C9 N3 -175.5(2) . . . . ? C7 C8 C9 C17 4.6(4) . . . . ? C7 C8 C16 N2 2.8(2) . . . . ? C7 C8 C16 C15 -175.22(18) . . . . ? C8 C9 C17 N4 4.9(8) . . . . ? C8 C9 C17 C18 -175.4(7) . . . . ? C8 C9 C17 N4A 27.2(6) . . . . ? C8 C9 C17 C18A -157.1(6) . . . . ? C9 N3 C10 C11 -174.0(2) . . . . ? C9 N3 C10 C15 3.9(3) . . . . ? C9 C8 C16 N2 -173.54(17) . . . . ? C9 C8 C16 C15 8.5(3) . . . . ? C9 C17 C18 C19 -178.3(7) . . . . ? C9 C17 N4A C21A 175.6(5) . . . . ? C9 C17 C18A C19A -176.8(6) . . . . ? C10 N3 C9 C8 -5.7(3) . . . . ? C10 N3 C9 C17 174.25(19) . . . . ? C10 C11 C12 C13 -0.1(4) . . . . ? C10 C15 C16 N2 172.68(19) . . . . ? C10 C15 C16 C8 -9.8(3) . . . . ? C11 C10 C15 C14 4.3(3) . . . . ? C11 C10 C15 C16 -178.2(2) . . . . ? C11 C12 C13 C14 3.7(4) . . . . ? C12 C13 C14 C15 -3.2(4) . . . . ? C13 C14 C15 C10 -0.8(3) . . . . ? C13 C14 C15 C16 -178.0(2) . . . . ? C14 C15 C16 N2 -10.1(4) . . . . ? C14 C15 C16 C8 167.4(2) . . . . ? C15 C10 C11 C12 -3.9(3) . . . . ? C16 N2 C6 C5 175.31(17) . . . . ? C16 N2 C6 C7 -0.1(2) . . . . ? C16 N2 B1 F1 77.4(3) . . . . ? C16 N2 B1 F2 -45.3(3) . . . . ? C16 N2 B1 N1 -164.43(18) . . . . ? C16 C8 C9 N3 -0.4(3) . . . . ? C16 C8 C9 C17 179.7(2) . . . . ? C17 N4 C21 C20 0.3(14) . . . . ? C17 C18 C19 C20 -6.5(17) . . . . ? C17 N4A C21A C20A -2.1(11) . . . . ? C17 C18A C19A C20A 5.0(14) . . . . ? C18 C19 C20 C21 8(2) . . . . ? C19 C20 C21 N4 -5.4(18) . . . . ? C21 N4 C17 C9 -178.6(6) . . . . ? C21 N4 C17 C18 1.7(12) . . . . ? C22 C5 C6 N2 174.57(18) . . . . ? C22 C5 C6 C7 -10.9(3) . . . . ? C22 C23 C24 C25 0.0(4) . . . . ? C23 C22 C27 C26 -0.7(3) . . . . ? C23 C22 C27 C30 178.8(2) . . . . ? C23 C24 C25 C26 -0.6(5) . . . . ? C23 C24 C25 C29 178.4(3) . . . . ? C24 C25 C26 C27 0.5(4) . . . . ? C25 C26 C27 C22 0.1(4) . . . . ? C25 C26 C27 C30 -179.4(3) . . . . ? C27 C22 C23 C24 0.6(4) . . . . ? C27 C22 C23 C28 -178.3(2) . . . . ? C28 C23 C24 C25 179.0(3) . . . . ? C29 C25 C26 C27 -178.5(3) . . . . ? B1 N1 C1 C2 176.29(19) . . . . ? B1 N1 C4 C3 -176.08(19) . . . . ? B1 N1 C4 C5 8.1(3) . . . . ? B1 N2 C6 C5 2.1(3) . . . . ? B1 N2 C6 C7 -173.30(18) . . . . ? B1 N2 C16 C8 171.05(19) . . . . ? B1 N2 C16 C15 -11.3(3) . . . . ? N4A C17 C18A C19A -1.6(10) . . . . ? C18A C17 N4A C21A 0.0(9) . . . . ? C18A C19A C20A C21A -6.7(17) . . . . ? C19A C20A C21A N4A 5.6(16) . . . . ?