#------------------------------------------------------------------------------ #$Date: 2023-09-23 00:55:23 +0300 (Sat, 23 Sep 2023) $ #$Revision: 286469 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/13/21/7132146.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_7132146 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 'C31 H24 B F2 N3' _chemical_formula_sum 'C31 H24 B F2 N3' _chemical_formula_weight 487.34 _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 110.660(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.3821(12) _cell_length_b 18.3455(15) _cell_length_c 11.4591(12) _cell_measurement_reflns_used 9894 _cell_measurement_temperature 300.00 _cell_measurement_theta_max 24.483 _cell_measurement_theta_min 2.833 _cell_volume 2435.6(4) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_collection 'Bruker D8 Venture 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 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method 'phi and omega 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 0.0693 _diffrn_reflns_av_unetI/netI 0.0271 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 65120 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.156 _diffrn_reflns_theta_max 25.156 _diffrn_reflns_theta_min 2.832 _diffrn_source 'sealed X-ray tube' _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_target Mo _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6277 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1083 before and 0.0747 after correction. The Ratio of minimum to maximum transmission is 0.8423. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear light red' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.329 _exptl_crystal_description block _exptl_crystal_F_000 1016 _exptl_crystal_recrystallization_method 'The crystals were growth by means of evaporation of a mixture of n-hexane and toluene at RT.' _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.363 _refine_diff_density_min -0.428 _refine_diff_density_rms 0.049 _refine_ls_extinction_coef 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2019/2 (Sheldrick 2019)' _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 430 _refine_ls_number_reflns 4352 _refine_ls_number_restraints 703 _refine_ls_restrained_S_all 1.038 _refine_ls_R_factor_all 0.0841 _refine_ls_R_factor_gt 0.0626 _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^)+(0.0771P)^2^+2.0030P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1601 _refine_ls_wR_factor_ref 0.1786 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3257 _reflns_number_total 4352 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3cc04460b2.cif _cod_data_source_block 3a _cod_database_code 7132146 _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 0.991 _shelx_estimated_absorpt_t_min 0.989 _exptl_crystal_mounting_method 'Crystals were removed from the crystallisation vial and immediately coated with polybutenes oil (CAS: 9003-29-6) on a glass slide. A suitable single crystal coated with polybutenes oil as less as possible was sealed in capillary tube filled with argon. The capillary tube with single crystal was mounted on copper pin with solid paraffin.' _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 C17A-C16 \\sim C17-C16 with sigma of 0.02 C5-C23 \\sim C5-C23A with sigma of 0.02 C29-C24 \\sim C29A-C24A with sigma of 0.02 C30-C26 \\sim C30A-C26A with sigma of 0.02 C31-C28 \\sim C31A-C28A with sigma of 0.02 3. Restrained planarity C5, C23, C24, C25, C26, C27, C28, C29, C30, C31 with sigma of 0.1 C5, C23A, C24A, C25A, C26A, C27A, C28A, C29A, C30A, C31A with sigma of 0.1 4. Uiso/Uaniso restraints and constraints C17 \\sim C18 \\sim C19 \\sim C20 \\sim C21 \\sim C22 \\sim C19A \\sim C17A \\sim C22A \\sim C20A \\sim C18A \\sim C21A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A C23 \\sim C24 \\sim C25 \\sim C26 \\sim C27 \\sim C28 \\sim C29 \\sim C30 \\sim C31 \\sim C23A \\sim C24A \\sim C25A \\sim C26A \\sim C27A \\sim C28A \\sim C29A \\sim C30A \\sim C31A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A 5. Rigid body (RIGU) restrains C16, C17, C18, C19, C20, C21, C22, C19A, C17A, C22A, C20A, C18A, C21A with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02 C5, C23, C24, C25, C26, C27, C28, C29, C30, C31, C23A, C24A, C25A, C26A, C27A, C28A, C29A, C30A, C31A with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02 6. Others Sof(C17A)=Sof(C22A)=Sof(H22A)=Sof(C21A)=Sof(H21A)=Sof(C20A)=Sof(H20A)= Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=1-FVAR(1) Sof(C17)=Sof(C18)=Sof(H18)=Sof(C19)=Sof(H19)=Sof(C20)=Sof(H20)=Sof(C21)= Sof(H21)=Sof(C22)=Sof(H22)=FVAR(1) Sof(C23A)=Sof(C24A)=Sof(C25A)=Sof(H25A)=Sof(C26A)=Sof(C27A)=Sof(H27A)= Sof(C28A)=Sof(C29A)=Sof(H29D)=Sof(H29E)=Sof(H29F)=Sof(C30A)=Sof(H30D)= Sof(H30E)=Sof(H30F)=Sof(C31A)=Sof(H31D)=Sof(H31E)=Sof(H31F)=1-FVAR(2) Sof(C23)=Sof(C24)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(C27)=Sof(H27)=Sof(C28)= Sof(C29)=Sof(H29A)=Sof(H29B)=Sof(H29C)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)= Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(H31C)=FVAR(2) 7.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2), C3(H3), C7(H7), C12(H12), C13(H13), C14(H14), C15(H15), C25(H25), C27(H27), C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C22A(H22A), C21A(H21A), C20A(H20A), C19A(H19A), C18A(H18A), C25A(H25A), C27A(H27A) 7.b Fitted hexagon refined as free rotating group: C23(C24,C25,C26,C27,C28), C17(C18,C19,C20,C21,C22), C17A(C22A,C21A,C20A,C19A, C18A), C23A(C24A,C25A,C26A,C27A,C28A) 7.c Idealised Me refined as rotating group: C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C), C29A(H29D,H29E, H29F), C30A(H30D,H30E,H30F), C31A(H31D,H31E,H31F) ; _shelx_res_file ; TITL 3a_a.res in P2(1)/c 3a.res created by SHELXL-2019/2 at 17:23:40 on 15-Sep-2023 REM Old TITL 3a in P2/c REM SHELXT solution in P2(1)/c: R1 0.235, Rweak 0.018, Alpha 0.042 REM 1.744 for 158 systematic absences, Orientation as input REM Formula found by SHELXT: C31 N3 F2 CELL 0.71073 12.3821 18.3455 11.4591 90 110.66 90 ZERR 4 0.0012 0.0015 0.0012 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H B F N UNIT 124 96 4 8 12 SADI 0.02 C17A C16 C17 C16 RIGU 0.01 0.02 C16 C17 C18 C19 C20 C21 C22 C19A C17A C22A C20A C18A C21A SIMU 0.01 0.02 2 C17 C18 C19 C20 C21 C22 C19A C17A C22A C20A C18A C21A SADI 0.02 C5 C23 C5 C23A RIGU 0.01 0.02 C5 C23 C24 C25 C26 C27 C28 C29 C30 C31 C23A C24A C25A C26A = C27A C28A C29A C30A C31A SIMU 0.01 0.02 2 C23 C24 C25 C26 C27 C28 C29 C30 C31 C23A C24A C25A C26A = C27A C28A C29A C30A C31A SADI 0.02 C29 C24 C29A C24A SADI 0.02 C30 C26 C30A C26A SADI 0.02 C31 C28 C31A C28A FLAT 0.1 C5 C23 C24 C25 C26 C27 C28 C29 C30 C31 FLAT 0.1 C5 C23A C24A C25A C26A C27A C28A C29A C30A C31A L.S. 10 PLAN 2 SIZE 0.1 0.12 0.13 TEMP 26.85 CONF BOND list 4 MORE -1 fmap 2 BOND $H ACTA REM REM REM WGHT 0.077100 2.003000 EXTI 0.014114 FVAR 0.59357 0.70679 0.70003 F1 4 0.383102 0.468598 0.420430 11.00000 0.07497 0.05839 = 0.06490 0.00389 0.04936 0.00551 F2 4 0.337360 0.434738 0.219530 11.00000 0.05484 0.05809 = 0.06002 -0.00342 0.01721 -0.00541 N1 5 0.459437 0.538355 0.291106 11.00000 0.04611 0.04433 = 0.03891 0.00231 0.01979 0.00380 N2 5 0.533226 0.413535 0.359410 11.00000 0.05161 0.04509 = 0.03928 0.00139 0.02270 0.00259 N3 5 0.651631 0.223908 0.562932 11.00000 0.09040 0.05166 = 0.05762 0.00537 0.01924 0.00490 C1 1 0.395888 0.598390 0.268697 11.00000 0.05000 0.05204 = 0.04951 0.00340 0.02273 0.00782 AFIX 43 H1 2 0.323163 0.601910 0.274860 11.00000 -1.20000 AFIX 0 C2 1 0.453024 0.655778 0.234504 11.00000 0.06015 0.04664 = 0.05328 0.00849 0.02179 0.00818 AFIX 43 H2 2 0.425860 0.703131 0.214927 11.00000 -1.20000 AFIX 0 C3 1 0.556022 0.629121 0.235327 11.00000 0.05507 0.05364 = 0.05110 0.00767 0.02291 -0.00039 AFIX 43 H3 2 0.612086 0.654736 0.215569 11.00000 -1.20000 AFIX 0 C4 1 0.561609 0.555157 0.271889 11.00000 0.04473 0.04867 = 0.04066 0.00291 0.01936 0.00129 C5 1 0.648636 0.504616 0.296608 11.00000 0.04394 0.05044 = 0.03498 -0.00133 0.01483 -0.00008 C6 1 0.635851 0.435626 0.346116 11.00000 0.04728 0.04831 = 0.03902 -0.00210 0.01860 0.00145 C7 1 0.720894 0.383555 0.397141 11.00000 0.04864 0.04992 = 0.05063 -0.00450 0.01427 0.00352 AFIX 43 H7 2 0.796473 0.385123 0.398730 11.00000 -1.20000 AFIX 0 C8 1 0.671111 0.328177 0.445797 11.00000 0.06182 0.04546 = 0.04608 -0.00318 0.01474 0.00516 C9 1 0.554400 0.347375 0.418000 11.00000 0.06423 0.04126 = 0.04160 -0.00036 0.02546 0.00332 C10 1 0.479152 0.298954 0.450544 11.00000 0.08003 0.04509 = 0.05690 0.00136 0.04276 0.00312 C11 1 0.535260 0.239480 0.527467 11.00000 0.09981 0.04557 = 0.05276 0.00277 0.03973 0.00330 C12 1 0.469003 0.190192 0.567382 11.00000 0.12590 0.05184 = 0.07600 0.01417 0.06108 0.00811 AFIX 43 H12 2 0.505474 0.152508 0.621126 11.00000 -1.20000 AFIX 0 C13 1 0.352425 0.196613 0.528806 11.00000 0.14542 0.05511 = 0.13274 0.02054 0.10576 0.00781 AFIX 43 H13 2 0.309810 0.163703 0.556765 11.00000 -1.20000 AFIX 0 C14 1 0.296259 0.252610 0.447111 11.00000 0.10349 0.06482 = 0.15864 0.03005 0.09441 0.01340 AFIX 43 H14 2 0.216102 0.255285 0.417137 11.00000 -1.20000 AFIX 0 C15 1 0.359391 0.303613 0.411162 11.00000 0.08531 0.05359 = 0.10242 0.01791 0.06237 0.00858 AFIX 43 H15 2 0.321579 0.341877 0.359698 11.00000 -1.20000 AFIX 0 C16 1 0.716045 0.263961 0.518647 11.00000 0.08302 0.04682 = 0.05623 -0.00390 0.01274 0.00437 PART 1 AFIX 66 C23 1 0.759674 0.525723 0.276291 31.00000 0.04005 0.04756 = 0.05140 -0.00282 0.02279 -0.00129 C24 1 0.771398 0.507584 0.163586 31.00000 0.05618 0.07143 = 0.05533 -0.00368 0.02711 -0.00744 C25 1 0.872378 0.524913 0.142751 31.00000 0.06291 0.08856 = 0.07390 -0.01044 0.04392 -0.01040 AFIX 43 H25 2 0.880222 0.512777 0.067343 31.00000 -1.20000 AFIX 65 C26 1 0.961634 0.560382 0.234620 31.00000 0.05368 0.07878 = 0.09884 -0.01019 0.03977 -0.01105 C27 1 0.949911 0.578521 0.347326 31.00000 0.04919 0.07136 = 0.09447 -0.02318 0.02591 -0.01021 AFIX 43 H27 2 1.009630 0.602252 0.408792 31.00000 -1.20000 AFIX 65 C28 1 0.848932 0.561193 0.368163 31.00000 0.04209 0.05765 = 0.07172 -0.02130 0.02171 -0.00484 AFIX 0 C29 1 0.676584 0.470618 0.058274 31.00000 0.06158 0.13032 = 0.05581 -0.01937 0.03219 -0.02734 AFIX 137 H29A 2 0.658157 0.424647 0.086670 31.00000 -1.50000 H29B 2 0.702319 0.462724 -0.010538 31.00000 -1.50000 H29C 2 0.609189 0.501059 0.031951 31.00000 -1.50000 AFIX 0 C30 1 1.076820 0.575351 0.217893 31.00000 0.06466 0.12150 = 0.15251 -0.01951 0.06716 -0.01866 AFIX 137 H30A 2 1.130871 0.537630 0.258122 31.00000 -1.50000 H30B 2 1.106427 0.621602 0.254470 31.00000 -1.50000 H30C 2 1.065460 0.576216 0.130589 31.00000 -1.50000 AFIX 0 C31 1 0.838701 0.583469 0.489779 31.00000 0.06530 0.10203 = 0.08447 -0.04544 0.02856 -0.01362 AFIX 137 H31A 2 0.803811 0.630843 0.481142 31.00000 -1.50000 H31B 2 0.914078 0.585009 0.553218 31.00000 -1.50000 H31C 2 0.791664 0.548812 0.512813 31.00000 -1.50000 AFIX 0 PART 0 B1 3 0.423975 0.461939 0.324030 11.00000 0.04889 0.04709 = 0.04167 0.00056 0.02162 0.00084 PART 1 AFIX 66 C17 1 0.832923 0.238322 0.543007 21.00000 0.06026 0.04865 = 0.11942 0.00749 -0.00699 0.00644 C18 1 0.886031 0.246106 0.455201 21.00000 0.05913 0.06164 = 0.16040 0.00117 0.01657 0.00802 AFIX 43 H18 2 0.847900 0.270010 0.380366 21.00000 -1.20000 AFIX 65 C19 1 0.996129 0.218164 0.479245 21.00000 0.06964 0.09179 = 0.19784 0.01601 0.02145 0.00640 AFIX 43 H19 2 1.031661 0.223373 0.420496 21.00000 -1.20000 AFIX 65 C20 1 1.053120 0.182437 0.591094 21.00000 0.07692 0.11280 = 0.20376 0.02239 0.00017 0.01256 AFIX 43 H20 2 1.126783 0.163742 0.607180 21.00000 -1.20000 AFIX 65 C21 1 1.000014 0.174652 0.678901 21.00000 0.08766 0.11434 = 0.18302 0.04191 -0.02473 0.01191 AFIX 43 H21 2 1.038146 0.150748 0.753736 21.00000 -1.20000 AFIX 65 C22 1 0.889916 0.202593 0.654859 21.00000 0.08475 0.09428 = 0.15149 0.03955 -0.02361 0.00190 AFIX 43 H22 2 0.854384 0.197385 0.713607 21.00000 -1.20000 AFIX 66 PART 2 C17A 1 0.850176 0.239392 0.565123 -21.00000 0.06614 0.06452 = 0.13516 0.01797 0.00241 0.00397 C22A 1 0.876217 0.167449 0.602523 -21.00000 0.07334 0.08181 = 0.14912 0.02476 -0.00500 0.00948 AFIX 43 H22A 2 0.817211 0.134792 0.597177 -21.00000 -1.20000 AFIX 65 C21A 1 0.990448 0.144316 0.647912 -21.00000 0.07811 0.09750 = 0.16847 0.01976 -0.00709 0.01687 AFIX 43 H21A 2 1.007870 0.096181 0.672935 -21.00000 -1.20000 AFIX 65 C20A 1 1.078639 0.193126 0.655903 -21.00000 0.08079 0.10516 = 0.17516 0.02564 0.00704 0.01110 AFIX 43 H20A 2 1.155067 0.177648 0.686272 -21.00000 -1.20000 AFIX 65 C19A 1 1.052599 0.265069 0.618503 -21.00000 0.07330 0.10256 = 0.17732 0.03034 0.01166 0.01118 AFIX 43 H19A 2 1.111605 0.297726 0.623850 -21.00000 -1.20000 AFIX 65 C18A 1 0.938369 0.288203 0.573113 -21.00000 0.06779 0.07863 = 0.15569 0.02190 0.01269 0.00406 AFIX 43 H18A 2 0.920947 0.336338 0.548090 -21.00000 -1.20000 AFIX 66 C23A 1 0.753605 0.513100 0.273002 -31.00000 0.04715 0.05314 = 0.05517 -0.00605 0.01840 -0.00176 C24A 1 0.760938 0.501089 0.156261 -31.00000 0.05108 0.07136 = 0.05510 -0.00249 0.02880 -0.00670 C25A 1 0.866177 0.508780 0.139455 -31.00000 0.06262 0.08778 = 0.07627 0.00128 0.03653 -0.00494 AFIX 43 H25A 2 0.871083 0.500744 0.061347 -31.00000 -1.20000 AFIX 65 C26A 1 0.964084 0.528483 0.239391 -31.00000 0.05331 0.08132 = 0.09018 -0.01203 0.04157 0.00021 C27A 1 0.956753 0.540493 0.356133 -31.00000 0.04806 0.07379 = 0.08679 -0.02214 0.02543 -0.00830 AFIX 43 H27A 2 1.022259 0.553675 0.422997 -31.00000 -1.20000 AFIX 65 C28A 1 0.851514 0.532802 0.372940 -31.00000 0.04972 0.06769 = 0.06981 -0.01543 0.02173 0.00085 AFIX 0 C29A 1 0.650743 0.481338 0.050250 -31.00000 0.05793 0.10303 = 0.04910 -0.01688 0.01276 0.01448 AFIX 137 H29D 2 0.650805 0.430144 0.032922 -31.00000 -1.50000 H29E 2 0.646232 0.508603 -0.022831 -31.00000 -1.50000 H29F 2 0.585425 0.492763 0.073541 -31.00000 -1.50000 AFIX 0 C30A 1 1.076584 0.533941 0.213801 -31.00000 0.06614 0.10304 = 0.13042 -0.00899 0.04669 -0.00731 AFIX 137 H30D 2 1.083615 0.492613 0.165587 -31.00000 -1.50000 H30E 2 1.140517 0.534767 0.291452 -31.00000 -1.50000 H30F 2 1.076455 0.577879 0.168252 -31.00000 -1.50000 AFIX 0 C31A 1 0.846631 0.550425 0.500793 -31.00000 0.05487 0.08211 = 0.06372 -0.02919 0.01568 -0.00448 AFIX 137 H31D 2 0.776136 0.575777 0.490974 -31.00000 -1.50000 H31E 2 0.911184 0.580611 0.545974 -31.00000 -1.50000 H31F 2 0.849494 0.506000 0.546061 -31.00000 -1.50000 AFIX 0 HKLF 4 REM 3a_a.res in P2(1)/c REM wR2 = 0.1786, GooF = S = 1.026, Restrained GooF = 1.038 for all data REM R1 = 0.0626 for 3257 Fo > 4sig(Fo) and 0.0841 for all 4352 data REM 430 parameters refined using 703 restraints END WGHT 0.0771 2.0030 REM Highest difference peak 0.363, deepest hole -0.428, 1-sigma level 0.049 Q1 1 1.0139 0.2261 0.5560 11.00000 0.05 0.36 Q2 1 1.0210 0.1724 0.6358 11.00000 0.05 0.34 ; _shelx_res_checksum 29047 _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 0.38310(14) 0.46860(9) 0.42043(15) 0.0595(5) Uani 1 1 d . . . . . F2 F 0.33736(13) 0.43474(9) 0.21953(15) 0.0585(5) Uani 1 1 d . . . . . N1 N 0.45944(17) 0.53836(11) 0.29111(18) 0.0418(5) Uani 1 1 d . . . . . N2 N 0.53323(18) 0.41353(11) 0.35941(18) 0.0435(5) Uani 1 1 d . . . . . N3 N 0.6516(3) 0.22391(14) 0.5629(2) 0.0684(7) Uani 1 1 d . . . . . C1 C 0.3959(2) 0.59839(14) 0.2687(2) 0.0491(6) Uani 1 1 d . . . . . H1 H 0.323163 0.601910 0.274860 0.059 Uiso 1 1 calc R U . . . C2 C 0.4530(2) 0.65578(15) 0.2345(3) 0.0529(7) Uani 1 1 d . . . . . H2 H 0.425860 0.703131 0.214927 0.063 Uiso 1 1 calc R U . . . C3 C 0.5560(2) 0.62912(15) 0.2353(2) 0.0522(7) Uani 1 1 d . . . . . H3 H 0.612086 0.654736 0.215569 0.063 Uiso 1 1 calc R U . . . C4 C 0.5616(2) 0.55516(14) 0.2719(2) 0.0435(6) Uani 1 1 d . . . . . C5 C 0.6486(2) 0.50462(14) 0.2966(2) 0.0429(6) Uani 1 1 d D . . . . C6 C 0.6359(2) 0.43563(14) 0.3461(2) 0.0440(6) Uani 1 1 d . . . . . C7 C 0.7209(2) 0.38355(14) 0.3971(2) 0.0506(6) Uani 1 1 d . . . . . H7 H 0.796473 0.385123 0.398730 0.061 Uiso 1 1 calc R U . . . C8 C 0.6711(2) 0.32818(15) 0.4458(2) 0.0523(7) Uani 1 1 d . . . . . C9 C 0.5544(2) 0.34737(14) 0.4180(2) 0.0472(6) Uani 1 1 d . . . . . C10 C 0.4792(3) 0.29895(14) 0.4505(3) 0.0557(7) Uani 1 1 d . . . . . C11 C 0.5353(3) 0.23948(15) 0.5275(3) 0.0626(8) Uani 1 1 d . . . . . C12 C 0.4690(4) 0.19019(18) 0.5674(3) 0.0777(10) Uani 1 1 d . . . . . H12 H 0.505474 0.152508 0.621126 0.093 Uiso 1 1 calc R U . . . C13 C 0.3524(4) 0.19661(19) 0.5288(4) 0.0959(14) Uani 1 1 d . . . . . H13 H 0.309810 0.163703 0.556765 0.115 Uiso 1 1 calc R U . . . C14 C 0.2963(4) 0.2526(2) 0.4471(4) 0.0960(14) Uani 1 1 d . . . . . H14 H 0.216102 0.255285 0.417137 0.115 Uiso 1 1 calc R U . . . C15 C 0.3594(3) 0.30361(17) 0.4112(4) 0.0726(10) Uani 1 1 d . . . . . H15 H 0.321579 0.341877 0.359698 0.087 Uiso 1 1 calc R U . . . C16 C 0.7160(3) 0.26396(16) 0.5186(3) 0.0652(8) Uani 1 1 d D . . . . C23 C 0.7597(3) 0.5257(3) 0.2763(6) 0.0445(11) Uani 0.700(11) 1 d DG U P A 1 C24 C 0.7714(4) 0.5076(3) 0.1636(5) 0.0590(13) Uani 0.700(11) 1 d DG U P A 1 C25 C 0.8724(5) 0.5249(3) 0.1428(4) 0.0698(14) Uani 0.700(11) 1 d G U P A 1 H25 H 0.880222 0.512777 0.067343 0.084 Uiso 0.700(11) 1 calc R U P A 1 C26 C 0.9616(4) 0.5604(4) 0.2346(5) 0.0736(15) Uani 0.700(11) 1 d DG U P A 1 C27 C 0.9499(3) 0.5785(4) 0.3473(4) 0.0715(15) Uani 0.700(11) 1 d G U P A 1 H27 H 1.009630 0.602252 0.408792 0.086 Uiso 0.700(11) 1 calc R U P A 1 C28 C 0.8489(4) 0.5612(3) 0.3682(4) 0.0567(12) Uani 0.700(11) 1 d DG U P A 1 C29 C 0.6766(8) 0.4706(7) 0.0583(10) 0.079(3) Uani 0.700(11) 1 d D U P A 1 H29A H 0.658157 0.424647 0.086670 0.119 Uiso 0.700(11) 1 calc R U P A 1 H29B H 0.702319 0.462724 -0.010538 0.119 Uiso 0.700(11) 1 calc R U P A 1 H29C H 0.609189 0.501059 0.031951 0.119 Uiso 0.700(11) 1 calc R U P A 1 C30 C 1.0768(6) 0.5754(5) 0.2179(10) 0.105(3) Uani 0.700(11) 1 d D U P A 1 H30A H 1.130871 0.537630 0.258122 0.158 Uiso 0.700(11) 1 calc R U P A 1 H30B H 1.106427 0.621602 0.254470 0.158 Uiso 0.700(11) 1 calc R U P A 1 H30C H 1.065460 0.576216 0.130589 0.158 Uiso 0.700(11) 1 calc R U P A 1 C31 C 0.8387(9) 0.5835(5) 0.4898(8) 0.083(2) Uani 0.700(11) 1 d D U P A 1 H31A H 0.803811 0.630843 0.481142 0.125 Uiso 0.700(11) 1 calc R U P A 1 H31B H 0.914078 0.585009 0.553218 0.125 Uiso 0.700(11) 1 calc R U P A 1 H31C H 0.791664 0.548812 0.512813 0.125 Uiso 0.700(11) 1 calc R U P A 1 B1 B 0.4240(3) 0.46194(16) 0.3240(3) 0.0444(7) Uani 1 1 d . . . . . C17 C 0.8329(3) 0.2383(2) 0.5430(4) 0.0865(16) Uani 0.707(4) 1 d DG U P B 1 C18 C 0.8860(3) 0.2461(2) 0.4552(4) 0.0997(17) Uani 0.707(4) 1 d G U P B 1 H18 H 0.847900 0.270010 0.380366 0.120 Uiso 0.707(4) 1 calc R U P B 1 C19 C 0.9961(3) 0.2182(3) 0.4792(5) 0.127(2) Uani 0.707(4) 1 d G U P B 1 H19 H 1.031661 0.223373 0.420496 0.152 Uiso 0.707(4) 1 calc R U P B 1 C20 C 1.0531(3) 0.1824(3) 0.5911(5) 0.144(2) Uani 0.707(4) 1 d G U P B 1 H20 H 1.126783 0.163742 0.607180 0.173 Uiso 0.707(4) 1 calc R U P B 1 C21 C 1.0000(4) 0.1747(3) 0.6789(4) 0.148(2) Uani 0.707(4) 1 d G U P B 1 H21 H 1.038146 0.150748 0.753736 0.177 Uiso 0.707(4) 1 calc R U P B 1 C22 C 0.8899(4) 0.2026(3) 0.6549(4) 0.128(2) Uani 0.707(4) 1 d G U P B 1 H22 H 0.854384 0.197385 0.713607 0.153 Uiso 0.707(4) 1 calc R U P B 1 C17A C 0.8502(6) 0.2394(6) 0.5651(12) 0.097(3) Uani 0.293(4) 1 d DG U P B 2 C22A C 0.8762(8) 0.1674(5) 0.6025(13) 0.113(3) Uani 0.293(4) 1 d G U P B 2 H22A H 0.817211 0.134792 0.597177 0.136 Uiso 0.293(4) 1 calc R U P B 2 C21A C 0.9904(9) 0.1443(5) 0.6479(13) 0.128(3) Uani 0.293(4) 1 d G U P B 2 H21A H 1.007870 0.096181 0.672935 0.154 Uiso 0.293(4) 1 calc R U P B 2 C20A C 1.0786(7) 0.1931(6) 0.6559(13) 0.131(3) Uani 0.293(4) 1 d G U P B 2 H20A H 1.155067 0.177648 0.686272 0.157 Uiso 0.293(4) 1 calc R U P B 2 C19A C 1.0526(7) 0.2651(6) 0.6185(13) 0.126(3) Uani 0.293(4) 1 d G U P B 2 H19A H 1.111605 0.297726 0.623850 0.152 Uiso 0.293(4) 1 calc R U P B 2 C18A C 0.9384(8) 0.2882(4) 0.5731(12) 0.108(3) Uani 0.293(4) 1 d G U P B 2 H18A H 0.920947 0.336338 0.548090 0.129 Uiso 0.293(4) 1 calc R U P B 2 C23A C 0.7536(8) 0.5131(5) 0.2730(14) 0.052(2) Uani 0.300(11) 1 d DG U P A 2 C24A C 0.7609(10) 0.5011(8) 0.1563(12) 0.056(2) Uani 0.300(11) 1 d DG U P A 2 C25A C 0.8662(13) 0.5088(8) 0.1395(10) 0.072(3) Uani 0.300(11) 1 d G U P A 2 H25A H 0.871083 0.500744 0.061347 0.087 Uiso 0.300(11) 1 calc R U P A 2 C26A C 0.9641(9) 0.5285(8) 0.2394(12) 0.071(2) Uani 0.300(11) 1 d DG U P A 2 C27A C 0.9568(8) 0.5405(8) 0.3561(10) 0.069(2) Uani 0.300(11) 1 d G U P A 2 H27A H 1.022259 0.553675 0.422997 0.083 Uiso 0.300(11) 1 calc R U P A 2 C28A C 0.8515(10) 0.5328(7) 0.3729(11) 0.062(2) Uani 0.300(11) 1 d DG U P A 2 C29A C 0.6507(19) 0.4813(16) 0.050(3) 0.072(5) Uani 0.300(11) 1 d D U P A 2 H29D H 0.650805 0.430144 0.032922 0.107 Uiso 0.300(11) 1 calc R U P A 2 H29E H 0.646232 0.508603 -0.022831 0.107 Uiso 0.300(11) 1 calc R U P A 2 H29F H 0.585425 0.492763 0.073541 0.107 Uiso 0.300(11) 1 calc R U P A 2 C30A C 1.0766(14) 0.5339(11) 0.214(2) 0.097(4) Uani 0.300(11) 1 d D U P A 2 H30D H 1.083615 0.492613 0.165587 0.145 Uiso 0.300(11) 1 calc R U P A 2 H30E H 1.140517 0.534767 0.291452 0.145 Uiso 0.300(11) 1 calc R U P A 2 H30F H 1.076455 0.577879 0.168252 0.145 Uiso 0.300(11) 1 calc R U P A 2 C31A C 0.847(2) 0.5504(10) 0.5008(16) 0.068(4) Uani 0.300(11) 1 d D U P A 2 H31D H 0.776136 0.575777 0.490974 0.102 Uiso 0.300(11) 1 calc R U P A 2 H31E H 0.911184 0.580611 0.545974 0.102 Uiso 0.300(11) 1 calc R U P A 2 H31F H 0.849494 0.506000 0.546061 0.102 Uiso 0.300(11) 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 0.0750(11) 0.0584(9) 0.0649(10) 0.0039(8) 0.0494(9) 0.0055(8) F2 0.0548(9) 0.0581(10) 0.0600(10) -0.0034(7) 0.0172(8) -0.0054(7) N1 0.0461(11) 0.0443(11) 0.0389(11) 0.0023(9) 0.0198(9) 0.0038(9) N2 0.0516(12) 0.0451(11) 0.0393(11) 0.0014(9) 0.0227(9) 0.0026(9) N3 0.090(2) 0.0517(15) 0.0576(15) 0.0054(12) 0.0192(14) 0.0049(14) C1 0.0500(15) 0.0520(15) 0.0495(15) 0.0034(12) 0.0227(12) 0.0078(12) C2 0.0602(16) 0.0466(15) 0.0533(15) 0.0085(12) 0.0218(13) 0.0082(13) C3 0.0551(16) 0.0536(16) 0.0511(15) 0.0077(12) 0.0229(13) -0.0004(12) C4 0.0447(14) 0.0487(14) 0.0407(13) 0.0029(11) 0.0194(11) 0.0013(11) C5 0.0439(14) 0.0504(14) 0.0350(12) -0.0013(10) 0.0148(10) -0.0001(11) C6 0.0473(14) 0.0483(14) 0.0390(13) -0.0021(11) 0.0186(11) 0.0014(11) C7 0.0486(15) 0.0499(15) 0.0506(15) -0.0045(12) 0.0143(12) 0.0035(12) C8 0.0618(17) 0.0455(14) 0.0461(14) -0.0032(12) 0.0147(12) 0.0052(12) C9 0.0642(17) 0.0413(13) 0.0416(13) -0.0004(10) 0.0255(12) 0.0033(12) C10 0.080(2) 0.0451(15) 0.0569(16) 0.0014(12) 0.0428(15) 0.0031(14) C11 0.100(3) 0.0456(16) 0.0528(16) 0.0028(13) 0.0397(17) 0.0033(15) C12 0.126(3) 0.0518(18) 0.076(2) 0.0142(16) 0.061(2) 0.0081(19) C13 0.145(4) 0.055(2) 0.133(4) 0.021(2) 0.106(3) 0.008(2) C14 0.103(3) 0.065(2) 0.159(4) 0.030(2) 0.094(3) 0.013(2) C15 0.085(2) 0.0536(18) 0.102(3) 0.0179(17) 0.062(2) 0.0086(16) C16 0.083(2) 0.0468(16) 0.0562(17) -0.0039(13) 0.0127(16) 0.0044(15) C23 0.040(2) 0.048(2) 0.051(2) -0.0028(19) 0.0228(18) -0.0013(17) C24 0.056(2) 0.071(3) 0.055(2) -0.004(2) 0.027(2) -0.007(2) C25 0.063(2) 0.089(3) 0.074(3) -0.010(2) 0.044(2) -0.010(2) C26 0.054(2) 0.079(4) 0.099(3) -0.010(3) 0.040(2) -0.011(2) C27 0.049(2) 0.071(4) 0.094(3) -0.023(3) 0.026(2) -0.010(2) C28 0.0421(19) 0.058(3) 0.072(2) -0.021(2) 0.0217(18) -0.005(2) C29 0.062(5) 0.130(7) 0.056(4) -0.019(4) 0.032(3) -0.027(5) C30 0.065(3) 0.121(6) 0.153(6) -0.020(6) 0.067(4) -0.019(4) C31 0.065(4) 0.102(6) 0.084(4) -0.045(4) 0.029(3) -0.014(5) B1 0.0489(16) 0.0471(16) 0.0417(15) 0.0006(12) 0.0216(13) 0.0008(13) C17 0.060(3) 0.049(2) 0.119(4) 0.007(2) -0.007(3) 0.006(2) C18 0.059(3) 0.062(3) 0.160(4) 0.001(3) 0.017(3) 0.008(2) C19 0.070(3) 0.092(3) 0.198(5) 0.016(4) 0.021(3) 0.006(3) C20 0.077(3) 0.113(4) 0.204(5) 0.022(4) 0.000(4) 0.013(3) C21 0.088(3) 0.114(4) 0.183(5) 0.042(4) -0.025(3) 0.012(3) C22 0.085(3) 0.094(4) 0.151(4) 0.040(3) -0.024(3) 0.002(3) C17A 0.066(4) 0.065(4) 0.135(5) 0.018(4) 0.002(4) 0.004(4) C22A 0.073(4) 0.082(5) 0.149(5) 0.025(5) -0.005(4) 0.009(4) C21A 0.078(4) 0.098(5) 0.168(6) 0.020(5) -0.007(5) 0.017(4) C20A 0.081(5) 0.105(5) 0.175(6) 0.026(5) 0.007(5) 0.011(4) C19A 0.073(4) 0.103(5) 0.177(6) 0.030(5) 0.012(4) 0.011(4) C18A 0.068(4) 0.079(4) 0.156(5) 0.022(4) 0.013(4) 0.004(4) C23A 0.047(4) 0.053(4) 0.055(4) -0.006(4) 0.018(3) -0.002(3) C24A 0.051(4) 0.071(4) 0.055(4) -0.002(4) 0.029(3) -0.007(4) C25A 0.063(4) 0.088(5) 0.076(4) 0.001(4) 0.037(4) -0.005(4) C26A 0.053(3) 0.081(5) 0.090(4) -0.012(4) 0.042(3) 0.000(4) C27A 0.048(3) 0.074(5) 0.087(4) -0.022(5) 0.025(3) -0.008(4) C28A 0.050(3) 0.068(5) 0.070(4) -0.015(4) 0.022(3) 0.001(4) C29A 0.058(8) 0.103(8) 0.049(7) -0.017(6) 0.013(6) 0.014(7) C30A 0.066(6) 0.103(10) 0.130(9) -0.009(9) 0.047(6) -0.007(8) C31A 0.055(6) 0.082(9) 0.064(6) -0.029(7) 0.016(5) -0.004(8) 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 107.2(2) . . ? C1 N1 B1 126.7(2) . . ? C4 N1 B1 126.0(2) . . ? C6 N2 B1 123.5(2) . . ? C9 N2 C6 106.7(2) . . ? C9 N2 B1 129.5(2) . . ? C16 N3 C11 118.9(3) . . ? N1 C1 H1 124.6 . . ? N1 C1 C2 110.8(2) . . ? C2 C1 H1 124.6 . . ? C1 C2 H2 126.5 . . ? C3 C2 C1 107.0(2) . . ? C3 C2 H2 126.5 . . ? C2 C3 H3 126.4 . . ? C2 C3 C4 107.1(2) . . ? C4 C3 H3 126.4 . . ? N1 C4 C3 107.9(2) . . ? C5 C4 N1 120.6(2) . . ? C5 C4 C3 131.4(2) . . ? C4 C5 C6 119.7(2) . . ? C4 C5 C23 118.8(3) . . ? C4 C5 C23A 126.0(4) . . ? C6 C5 C23 121.5(3) . . ? C6 C5 C23A 114.3(4) . . ? N2 C6 C5 122.6(2) . . ? C7 C6 N2 109.8(2) . . ? C7 C6 C5 127.4(2) . . ? C6 C7 H7 126.5 . . ? C6 C7 C8 106.9(2) . . ? C8 C7 H7 126.5 . . ? C7 C8 C9 106.8(2) . . ? C7 C8 C16 133.7(3) . . ? C9 C8 C16 119.4(3) . . ? N2 C9 C8 109.7(2) . . ? N2 C9 C10 130.6(3) . . ? C8 C9 C10 119.8(2) . . ? C11 C10 C9 114.7(3) . . ? C15 C10 C9 126.5(3) . . ? C15 C10 C11 118.7(3) . . ? N3 C11 C10 124.9(3) . . ? N3 C11 C12 116.1(3) . . ? C12 C11 C10 118.9(3) . . ? C11 C12 H12 119.5 . . ? C13 C12 C11 121.0(3) . . ? C13 C12 H12 119.5 . . ? C12 C13 H13 119.9 . . ? C12 C13 C14 120.1(3) . . ? C14 C13 H13 119.9 . . ? C13 C14 H14 120.0 . . ? C15 C14 C13 120.0(4) . . ? C15 C14 H14 120.0 . . ? C10 C15 H15 119.5 . . ? C14 C15 C10 121.0(3) . . ? C14 C15 H15 119.5 . . ? N3 C16 C8 121.4(3) . . ? N3 C16 C17 116.4(3) . . ? N3 C16 C17A 114.2(5) . . ? C8 C16 C17 122.2(3) . . ? C8 C16 C17A 124.1(5) . . ? C24 C23 C5 118.5(4) . . ? C24 C23 C28 120.0 . . ? C28 C23 C5 121.5(4) . . ? C23 C24 C29 122.8(6) . . ? C25 C24 C23 120.0 . . ? C25 C24 C29 117.2(6) . . ? C24 C25 H25 120.0 . . ? C24 C25 C26 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C30 121.1(5) . . ? C27 C26 C25 120.0 . . ? C27 C26 C30 118.8(5) . . ? C26 C27 H27 120.0 . . ? C28 C27 C26 120.0 . . ? C28 C27 H27 120.0 . . ? C23 C28 C31 121.7(5) . . ? C27 C28 C23 120.0 . . ? C27 C28 C31 118.2(5) . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29B 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C26 C30 H30A 109.5 . . ? C26 C30 H30B 109.5 . . ? C26 C30 H30C 109.5 . . ? H30A C30 H30B 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C28 C31 H31A 109.5 . . ? C28 C31 H31B 109.5 . . ? C28 C31 H31C 109.5 . . ? H31A C31 H31B 109.5 . . ? H31A C31 H31C 109.5 . . ? H31B C31 H31C 109.5 . . ? F1 B1 F2 109.5(2) . . ? F1 B1 N1 109.3(2) . . ? F1 B1 N2 112.1(2) . . ? F2 B1 N1 108.3(2) . . ? F2 B1 N2 110.9(2) . . ? N2 B1 N1 106.6(2) . . ? C18 C17 C16 121.4(3) . . ? C18 C17 C22 120.0 . . ? C22 C17 C16 118.5(3) . . ? C17 C18 H18 120.0 . . ? C19 C18 C17 120.0 . . ? C19 C18 H18 120.0 . . ? C18 C19 H19 120.0 . . ? C20 C19 C18 120.0 . . ? C20 C19 H19 120.0 . . ? C19 C20 H20 120.0 . . ? C19 C20 C21 120.0 . . ? C21 C20 H20 120.0 . . ? C20 C21 H21 120.0 . . ? C22 C21 C20 120.0 . . ? C22 C21 H21 120.0 . . ? C17 C22 H22 120.0 . . ? C21 C22 C17 120.0 . . ? C21 C22 H22 120.0 . . ? C22A C17A C16 117.7(6) . . ? C22A C17A C18A 120.0 . . ? C18A C17A C16 122.2(6) . . ? C17A C22A H22A 120.0 . . ? C17A C22A C21A 120.0 . . ? C21A C22A H22A 120.0 . . ? C22A C21A H21A 120.0 . . ? C22A C21A C20A 120.0 . . ? C20A C21A H21A 120.0 . . ? C21A C20A H20A 120.0 . . ? C19A C20A C21A 120.0 . . ? C19A C20A H20A 120.0 . . ? C20A C19A H19A 120.0 . . ? C20A C19A C18A 120.0 . . ? C18A C19A H19A 120.0 . . ? C17A C18A H18A 120.0 . . ? C19A C18A C17A 120.0 . . ? C19A C18A H18A 120.0 . . ? C24A C23A C5 122.6(9) . . ? C24A C23A C28A 120.0 . . ? C28A C23A C5 117.4(9) . . ? C23A C24A C25A 120.0 . . ? C23A C24A C29A 117.6(16) . . ? C25A C24A C29A 122.4(16) . . ? C24A C25A H25A 120.0 . . ? C26A C25A C24A 120.0 . . ? C26A C25A H25A 120.0 . . ? C25A C26A C27A 120.0 . . ? C25A C26A C30A 116.7(11) . . ? C27A C26A C30A 123.3(11) . . ? C26A C27A H27A 120.0 . . ? C26A C27A C28A 120.0 . . ? C28A C27A H27A 120.0 . . ? C23A C28A C31A 121.9(11) . . ? C27A C28A C23A 120.0 . . ? C27A C28A C31A 118.0(11) . . ? C24A C29A H29D 109.5 . . ? C24A C29A H29E 109.5 . . ? C24A C29A H29F 109.5 . . ? H29D C29A H29E 109.5 . . ? H29D C29A H29F 109.5 . . ? H29E C29A H29F 109.5 . . ? C26A C30A H30D 109.5 . . ? C26A C30A H30E 109.5 . . ? C26A C30A H30F 109.5 . . ? H30D C30A H30E 109.5 . . ? H30D C30A H30F 109.5 . . ? H30E C30A H30F 109.5 . . ? C28A C31A H31D 109.5 . . ? C28A C31A H31E 109.5 . . ? C28A C31A H31F 109.5 . . ? H31D C31A H31E 109.5 . . ? H31D C31A H31F 109.5 . . ? H31E C31A H31F 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 B1 1.373(3) . ? F2 B1 1.388(3) . ? N1 C1 1.325(3) . ? N1 C4 1.393(3) . ? N1 B1 1.555(4) . ? N2 C6 1.392(3) . ? N2 C9 1.367(3) . ? N2 B1 1.548(4) . ? N3 C11 1.382(4) . ? N3 C16 1.311(4) . ? C1 H1 0.9300 . ? C1 C2 1.399(4) . ? C2 H2 0.9300 . ? C2 C3 1.363(4) . ? C3 H3 0.9300 . ? C3 C4 1.415(4) . ? C4 C5 1.373(3) . ? C5 C6 1.419(4) . ? C5 C23 1.523(4) . ? C5 C23A 1.426(9) . ? C6 C7 1.389(4) . ? C7 H7 0.9300 . ? C7 C8 1.402(4) . ? C8 C9 1.410(4) . ? C8 C16 1.438(4) . ? C9 C10 1.429(4) . ? C10 C11 1.421(4) . ? C10 C15 1.392(4) . ? C11 C12 1.402(4) . ? C12 H12 0.9300 . ? C12 C13 1.357(6) . ? C13 H13 0.9300 . ? C13 C14 1.399(6) . ? C14 H14 0.9300 . ? C14 C15 1.372(4) . ? C15 H15 0.9300 . ? C16 C17 1.452(4) . ? C16 C17A 1.619(8) . ? C23 C24 1.3900 . ? C23 C28 1.3900 . ? C24 C25 1.3900 . ? C24 C29 1.515(7) . ? C25 H25 0.9300 . ? C25 C26 1.3900 . ? C26 C27 1.3900 . ? C26 C30 1.529(6) . ? C27 H27 0.9300 . ? C27 C28 1.3900 . ? C28 C31 1.500(7) . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 H31A 0.9600 . ? C31 H31B 0.9600 . ? C31 H31C 0.9600 . ? C17 C18 1.3900 . ? C17 C22 1.3900 . ? C18 H18 0.9300 . ? C18 C19 1.3900 . ? C19 H19 0.9300 . ? C19 C20 1.3900 . ? C20 H20 0.9300 . ? C20 C21 1.3900 . ? C21 H21 0.9300 . ? C21 C22 1.3900 . ? C22 H22 0.9300 . ? C17A C22A 1.3900 . ? C17A C18A 1.3900 . ? C22A H22A 0.9300 . ? C22A C21A 1.3900 . ? C21A H21A 0.9300 . ? C21A C20A 1.3900 . ? C20A H20A 0.9300 . ? C20A C19A 1.3900 . ? C19A H19A 0.9300 . ? C19A C18A 1.3900 . ? C18A H18A 0.9300 . ? C23A C24A 1.3900 . ? C23A C28A 1.3900 . ? C24A C25A 1.3900 . ? C24A C29A 1.516(14) . ? C25A H25A 0.9300 . ? C25A C26A 1.3900 . ? C26A C27A 1.3900 . ? C26A C30A 1.525(13) . ? C27A H27A 0.9300 . ? C27A C28A 1.3900 . ? C28A C31A 1.522(13) . ? C29A H29D 0.9600 . ? C29A H29E 0.9600 . ? C29A H29F 0.9600 . ? C30A H30D 0.9600 . ? C30A H30E 0.9600 . ? C30A H30F 0.9600 . ? C31A H31D 0.9600 . ? C31A H31E 0.9600 . ? C31A H31F 0.9600 . ? 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 0.4(3) . . . . ? N1 C4 C5 C6 -2.2(4) . . . . ? N1 C4 C5 C23 -179.0(3) . . . . ? N1 C4 C5 C23A 175.4(8) . . . . ? N2 C6 C7 C8 -1.2(3) . . . . ? N2 C9 C10 C11 -171.2(3) . . . . ? N2 C9 C10 C15 11.1(5) . . . . ? N3 C11 C12 C13 -174.1(3) . . . . ? N3 C16 C17 C18 143.4(3) . . . . ? N3 C16 C17 C22 -33.9(4) . . . . ? N3 C16 C17A C22A 24.3(9) . . . . ? N3 C16 C17A C18A -153.1(7) . . . . ? C1 N1 C4 C3 -0.5(3) . . . . ? C1 N1 C4 C5 175.4(2) . . . . ? C1 N1 B1 F1 -50.9(3) . . . . ? C1 N1 B1 F2 68.4(3) . . . . ? C1 N1 B1 N2 -172.2(2) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C2 C3 C4 N1 0.7(3) . . . . ? C2 C3 C4 C5 -174.5(3) . . . . ? C3 C4 C5 C6 172.6(3) . . . . ? C3 C4 C5 C23 -4.2(5) . . . . ? C3 C4 C5 C23A -9.8(9) . . . . ? C4 N1 C1 C2 0.0(3) . . . . ? C4 N1 B1 F1 133.6(2) . . . . ? C4 N1 B1 F2 -107.2(3) . . . . ? C4 N1 B1 N2 12.2(3) . . . . ? C4 C5 C6 N2 6.7(4) . . . . ? C4 C5 C6 C7 -167.5(2) . . . . ? C4 C5 C23 C24 -95.4(3) . . . . ? C4 C5 C23 C28 85.8(4) . . . . ? C4 C5 C23A C24A -82.0(7) . . . . ? C4 C5 C23A C28A 99.3(8) . . . . ? C5 C6 C7 C8 173.6(2) . . . . ? C5 C23 C24 C25 -178.9(3) . . . . ? C5 C23 C24 C29 2.6(7) . . . . ? C5 C23 C28 C27 178.9(3) . . . . ? C5 C23 C28 C31 -2.7(5) . . . . ? C5 C23A C24A C25A -178.7(6) . . . . ? C5 C23A C24A C29A 2.6(14) . . . . ? C5 C23A C28A C27A 178.8(6) . . . . ? C5 C23A C28A C31A -4.5(11) . . . . ? C6 N2 C9 C8 1.9(3) . . . . ? C6 N2 C9 C10 -177.4(3) . . . . ? C6 N2 B1 F1 -126.9(2) . . . . ? C6 N2 B1 F2 110.3(3) . . . . ? C6 N2 B1 N1 -7.3(3) . . . . ? C6 C5 C23 C24 87.9(3) . . . . ? C6 C5 C23 C28 -91.0(4) . . . . ? C6 C5 C23A C24A 95.7(6) . . . . ? C6 C5 C23A C28A -83.0(7) . . . . ? C6 C7 C8 C9 2.3(3) . . . . ? C6 C7 C8 C16 -173.5(3) . . . . ? C7 C8 C9 N2 -2.6(3) . . . . ? C7 C8 C9 C10 176.7(2) . . . . ? C7 C8 C16 N3 173.4(3) . . . . ? C7 C8 C16 C17 -9.1(5) . . . . ? C7 C8 C16 C17A 0.0(7) . . . . ? C8 C9 C10 C11 9.6(4) . . . . ? C8 C9 C10 C15 -168.1(3) . . . . ? C8 C16 C17 C18 -34.2(4) . . . . ? C8 C16 C17 C22 148.5(3) . . . . ? C8 C16 C17A C22A -161.9(6) . . . . ? C8 C16 C17A C18A 20.8(11) . . . . ? C9 N2 C6 C5 -175.5(2) . . . . ? C9 N2 C6 C7 -0.4(3) . . . . ? C9 N2 B1 F1 46.2(3) . . . . ? C9 N2 B1 F2 -76.6(3) . . . . ? C9 N2 B1 N1 165.8(2) . . . . ? C9 C8 C16 N3 -2.0(4) . . . . ? C9 C8 C16 C17 175.5(3) . . . . ? C9 C8 C16 C17A -175.4(6) . . . . ? C9 C10 C11 N3 -4.8(4) . . . . ? C9 C10 C11 C12 178.1(3) . . . . ? C9 C10 C15 C14 178.7(3) . . . . ? C10 C11 C12 C13 3.2(5) . . . . ? C11 N3 C16 C8 7.0(4) . . . . ? C11 N3 C16 C17 -170.6(3) . . . . ? C11 N3 C16 C17A -179.0(5) . . . . ? C11 C10 C15 C14 1.0(5) . . . . ? C11 C12 C13 C14 0.6(6) . . . . ? C12 C13 C14 C15 -3.6(6) . . . . ? C13 C14 C15 C10 2.8(6) . . . . ? C15 C10 C11 N3 173.1(3) . . . . ? C15 C10 C11 C12 -3.9(4) . . . . ? C16 N3 C11 C10 -3.6(4) . . . . ? C16 N3 C11 C12 173.5(3) . . . . ? C16 C8 C9 N2 173.9(2) . . . . ? C16 C8 C9 C10 -6.8(4) . . . . ? C16 C17 C18 C19 -177.2(4) . . . . ? C16 C17 C22 C21 177.3(4) . . . . ? C16 C17A C22A C21A -177.4(10) . . . . ? C16 C17A C18A C19A 177.3(11) . . . . ? C23 C5 C6 N2 -176.5(3) . . . . ? C23 C5 C6 C7 9.3(5) . . . . ? C23 C24 C25 C26 0.0 . . . . ? C24 C23 C28 C27 0.0 . . . . ? C24 C23 C28 C31 178.4(5) . . . . ? C24 C25 C26 C27 0.0 . . . . ? C24 C25 C26 C30 175.7(5) . . . . ? C25 C26 C27 C28 0.0 . . . . ? C26 C27 C28 C23 0.0 . . . . ? C26 C27 C28 C31 -178.5(5) . . . . ? C28 C23 C24 C25 0.0 . . . . ? C28 C23 C24 C29 -178.5(7) . . . . ? C29 C24 C25 C26 178.5(7) . . . . ? C30 C26 C27 C28 -175.8(5) . . . . ? B1 N1 C1 C2 -176.2(2) . . . . ? B1 N1 C4 C3 175.8(2) . . . . ? B1 N1 C4 C5 -8.3(4) . . . . ? B1 N2 C6 C5 -1.1(3) . . . . ? B1 N2 C6 C7 174.0(2) . . . . ? B1 N2 C9 C8 -172.1(2) . . . . ? B1 N2 C9 C10 8.6(4) . . . . ? C17 C18 C19 C20 0.0 . . . . ? C18 C17 C22 C21 0.0 . . . . ? C18 C19 C20 C21 0.0 . . . . ? C19 C20 C21 C22 0.0 . . . . ? C20 C21 C22 C17 0.0 . . . . ? C22 C17 C18 C19 0.0 . . . . ? C17A C22A C21A C20A 0.0 . . . . ? C22A C17A C18A C19A 0.0 . . . . ? C22A C21A C20A C19A 0.0 . . . . ? C21A C20A C19A C18A 0.0 . . . . ? C20A C19A C18A C17A 0.0 . . . . ? C18A C17A C22A C21A 0.0 . . . . ? C23A C5 C6 N2 -171.1(7) . . . . ? C23A C5 C6 C7 14.7(7) . . . . ? C23A C24A C25A C26A 0.0 . . . . ? C24A C23A C28A C27A 0.0 . . . . ? C24A C23A C28A C31A 176.7(10) . . . . ? C24A C25A C26A C27A 0.0 . . . . ? C24A C25A C26A C30A 178.6(10) . . . . ? C25A C26A C27A C28A 0.0 . . . . ? C26A C27A C28A C23A 0.0 . . . . ? C26A C27A C28A C31A -176.8(10) . . . . ? C28A C23A C24A C25A 0.0 . . . . ? C28A C23A C24A C29A -178.7(15) . . . . ? C29A C24A C25A C26A 178.6(16) . . . . ? C30A C26A C27A C28A -178.5(11) . . . . ?