#------------------------------------------------------------------------------ #$Date: 2020-10-06 10:42:34 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257416 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557382.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_1557382 loop_ _publ_author_name 'Kim, Inwon' 'Im, Honggu' 'Lee, Hyeonyeong' 'Hong, Sungwoo' _publ_section_title ; N-Heterocyclic carbene-catalyzed deaminative cross-coupling of aldehydes with Katritzky pyridinium salts ; _journal_issue 12 _journal_name_full 'Chemical Science' _journal_page_first 3192 _journal_page_last 3197 _journal_paper_doi 10.1039/D0SC00225A _journal_volume 11 _journal_year 2020 _chemical_formula_sum 'C33 H28 B F4 N O2' _chemical_formula_weight 557.37 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-11-08 deposited with the CCDC. 2020-02-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.639(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.0604(6) _cell_length_b 16.6780(9) _cell_length_c 15.1704(8) _cell_measurement_reflns_used 9983 _cell_measurement_temperature 153(2) _cell_measurement_theta_max 28.27 _cell_measurement_theta_min 3.08 _cell_volume 2750.3(3) _computing_cell_refinement 'Bruker APEXIII' _computing_data_collection 'Bruker APEXIII' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ORTEP _computing_publication_material CIFTAB _computing_structure_refinement SHELXL _computing_structure_solution SHELXS _diffrn_ambient_temperature 153(2) _diffrn_measured_fraction_theta_full 0.989 _diffrn_measured_fraction_theta_max 0.989 _diffrn_measurement_device_type 'Bruker Photon II CMOS detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0360 _diffrn_reflns_av_unetI/netI 0.0240 _diffrn_reflns_Laue_measured_fraction_full 0.989 _diffrn_reflns_Laue_measured_fraction_max 0.989 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 46862 _diffrn_reflns_point_group_measured_fraction_full 0.989 _diffrn_reflns_point_group_measured_fraction_max 0.989 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.278 _diffrn_reflns_theta_min 2.993 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.7034 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.346 _exptl_crystal_description block _exptl_crystal_F_000 1160 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM/EA/Pentane' _exptl_crystal_size_max 0.321 _exptl_crystal_size_mid 0.178 _exptl_crystal_size_min 0.142 _refine_diff_density_max 0.344 _refine_diff_density_min -0.202 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 417 _refine_ls_number_reflns 6750 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_R_factor_all 0.0531 _refine_ls_R_factor_gt 0.0418 _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^)+(0.0408P)^2^+1.2335P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0963 _refine_ls_wR_factor_ref 0.1035 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5587 _reflns_number_total 6750 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00225a2.cif _cod_data_source_block A19237O_014 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 1557380--1557383.cif. Adding full bibliography for 1557380--1557383.cif. ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1557382 _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 0.968 _shelx_estimated_absorpt_t_max 0.986 _shelx_res_file ; TITL A19237O_014 in P2(1)/n A19237O_014.res created by SHELXL-2018/3 at 18:32:59 on 15-Oct-2019 CELL 0.71073 11.06040 16.67800 15.17040 90.0000 100.6387 90.0000 ZERR 4.00 0.00060 0.00090 0.00080 0.0000 0.0021 0.0000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H B N O F UNIT 132 112 4 4 8 16 TEMP -120.3 SIZE 0.142 0.178 0.321 CONF MERG 2 ACTA OMIT -1 1 2 OMIT 1 17 0 OMIT 4 14 8 OMIT 3 20 4 OMIT 2 1 0 OMIT 2 17 1 L.S. 12 BOND $H FMAP 2 PLAN 20 LIST 4 WGHT 0.040800 1.233500 FVAR 0.28530 0.60439 N1 4 0.504581 0.383866 0.353529 11.00000 0.01933 0.01608 = 0.01660 0.00129 0.00090 -0.00098 C2 1 0.539022 0.309350 0.387292 11.00000 0.02212 0.01651 = 0.01629 0.00106 0.00367 -0.00077 C3 1 0.655825 0.297786 0.436120 11.00000 0.02220 0.01669 = 0.01977 0.00331 0.00255 0.00025 AFIX 43 H3 2 0.679293 0.245751 0.458417 11.00000 -1.20000 AFIX 0 C4 1 0.740583 0.360490 0.453693 11.00000 0.01946 0.02097 = 0.01606 0.00140 0.00383 -0.00101 C5 1 0.700205 0.435835 0.421314 11.00000 0.02192 0.01771 = 0.01932 -0.00035 0.00291 -0.00314 AFIX 43 H5 2 0.754242 0.480366 0.433639 11.00000 -1.20000 AFIX 0 C6 1 0.583654 0.447520 0.371750 11.00000 0.02233 0.01623 = 0.01777 0.00008 0.00378 -0.00096 C7 1 0.865938 0.347151 0.505519 11.00000 0.01893 0.02410 = 0.01985 0.00492 0.00304 -0.00165 C8 1 0.921568 0.271796 0.506673 11.00000 0.02391 0.02417 = 0.02893 0.00544 0.00344 0.00037 AFIX 43 H8 2 0.878531 0.228652 0.474033 11.00000 -1.20000 AFIX 0 C9 1 1.039596 0.259658 0.555361 11.00000 0.02593 0.03444 = 0.03774 0.01184 0.00522 0.00635 AFIX 43 H9 2 1.076928 0.208334 0.555671 11.00000 -1.20000 AFIX 0 C10 1 1.102968 0.322208 0.603448 11.00000 0.02006 0.04854 = 0.03139 0.01249 -0.00039 -0.00014 AFIX 43 H10 2 1.183759 0.313746 0.636316 11.00000 -1.20000 AFIX 0 C11 1 1.048507 0.397144 0.603612 11.00000 0.02485 0.04073 = 0.02749 0.00344 -0.00067 -0.00869 AFIX 43 H11 2 1.091633 0.439838 0.637049 11.00000 -1.20000 AFIX 0 C12 1 0.930496 0.409682 0.554672 11.00000 0.02406 0.02798 = 0.02611 0.00190 0.00222 -0.00299 AFIX 43 H12 2 0.893567 0.461110 0.554680 11.00000 -1.20000 AFIX 0 C13 1 0.452834 0.239908 0.372714 11.00000 0.02124 0.01695 = 0.01970 0.00413 -0.00213 -0.00218 C14 1 0.360629 0.230833 0.423175 11.00000 0.02597 0.02134 = 0.02968 0.00371 0.00467 -0.00061 AFIX 43 H14 2 0.347971 0.270937 0.465006 11.00000 -1.20000 AFIX 0 C15 1 0.287076 0.162472 0.411835 11.00000 0.02690 0.03034 = 0.04140 0.00884 0.00504 -0.00617 AFIX 43 H15 2 0.223523 0.156124 0.445696 11.00000 -1.20000 AFIX 0 C16 1 0.306164 0.103909 0.351588 11.00000 0.03769 0.02523 = 0.03531 0.00617 -0.00771 -0.01386 AFIX 43 H16 2 0.254663 0.057905 0.343290 11.00000 -1.20000 AFIX 0 C17 1 0.399939 0.111929 0.303264 11.00000 0.05228 0.02114 = 0.02500 -0.00193 -0.00050 -0.00835 AFIX 43 H17 2 0.413470 0.071051 0.262566 11.00000 -1.20000 AFIX 0 C18 1 0.474300 0.179504 0.314057 11.00000 0.03654 0.02177 = 0.02176 0.00134 0.00442 -0.00318 AFIX 43 H18 2 0.539590 0.184580 0.281593 11.00000 -1.20000 AFIX 0 C19 1 0.545727 0.529919 0.339556 11.00000 0.02324 0.01448 = 0.02078 0.00074 -0.00162 -0.00180 C20 1 0.462696 0.573354 0.379100 11.00000 0.04097 0.02118 = 0.02447 0.00178 0.00803 0.00309 AFIX 43 H20 2 0.424867 0.549286 0.423875 11.00000 -1.20000 AFIX 0 C21 1 0.435208 0.652100 0.352921 11.00000 0.05308 0.02251 = 0.03295 0.00034 0.00932 0.01167 AFIX 43 H21 2 0.377927 0.681789 0.379438 11.00000 -1.20000 AFIX 0 C22 1 0.491047 0.687243 0.288418 11.00000 0.05597 0.01830 = 0.04164 0.00809 0.00732 0.00606 AFIX 43 H22 2 0.472622 0.741245 0.271019 11.00000 -1.20000 AFIX 0 C23 1 0.573514 0.644201 0.249143 11.00000 0.04896 0.02527 = 0.04395 0.01357 0.01490 -0.00128 AFIX 43 H23 2 0.611352 0.668724 0.204642 11.00000 -1.20000 AFIX 0 C24 1 0.601674 0.565262 0.274156 11.00000 0.03169 0.02255 = 0.03616 0.00580 0.01002 0.00025 AFIX 43 H24 2 0.658434 0.535721 0.246973 11.00000 -1.20000 AFIX 0 C25 1 0.382683 0.396037 0.293121 11.00000 0.01933 0.01658 = 0.01803 0.00080 -0.00169 0.00083 AFIX 13 H25 2 0.385405 0.451574 0.268717 11.00000 -1.20000 AFIX 0 C26 1 0.360316 0.340285 0.210195 11.00000 0.02465 0.01933 = 0.01817 -0.00057 -0.00037 0.00252 AFIX 23 H26A 2 0.440202 0.319218 0.199837 11.00000 -1.20000 H26B 2 0.309443 0.294126 0.222185 11.00000 -1.20000 AFIX 0 C27 1 0.296064 0.383521 0.126389 11.00000 0.02595 0.01673 = 0.01719 -0.00271 -0.00012 0.00298 C28 1 0.169055 0.377948 0.097560 11.00000 0.02690 0.02097 = 0.02226 -0.00205 -0.00052 -0.00212 AFIX 43 H28 2 0.120978 0.347773 0.131515 11.00000 -1.20000 AFIX 0 C29 1 0.112276 0.416450 0.019138 11.00000 0.02912 0.02558 = 0.02761 -0.00413 -0.00777 0.00160 AFIX 43 H29 2 0.025704 0.412502 0.000093 11.00000 -1.20000 AFIX 0 C30 1 0.181197 0.460259 -0.030951 11.00000 0.04354 0.02808 = 0.02031 0.00267 -0.00505 0.00550 AFIX 43 H30 2 0.142310 0.486102 -0.084537 11.00000 -1.20000 AFIX 0 C31 1 0.307370 0.466361 -0.002697 11.00000 0.04107 0.03174 = 0.02626 0.00696 0.00771 0.00099 AFIX 43 H31 2 0.354999 0.496550 -0.036971 11.00000 -1.20000 AFIX 0 C32 1 0.364606 0.428402 0.075751 11.00000 0.02499 0.02891 = 0.02612 0.00121 0.00358 0.00310 AFIX 43 H32 2 0.451067 0.433156 0.094873 11.00000 -1.20000 AFIX 0 C33 1 0.283689 0.398123 0.351522 11.00000 0.02206 0.01769 = 0.02275 -0.00022 0.00048 0.00117 O34 5 0.302098 0.423465 0.427046 11.00000 0.02863 0.03608 = 0.02488 -0.00909 0.00413 -0.00309 O35 5 0.176677 0.371983 0.307146 11.00000 0.02011 0.03817 = 0.02489 -0.00549 0.00146 -0.00172 C36 1 0.075374 0.372705 0.356450 11.00000 0.02188 0.05656 = 0.03895 -0.01537 0.00880 -0.00518 AFIX 137 H36A 2 0.008651 0.338522 0.325675 11.00000 -1.50000 H36B 2 0.045143 0.427683 0.359506 11.00000 -1.50000 H36C 2 0.104215 0.352398 0.417319 11.00000 -1.50000 AFIX 0 PART 1 21 B37 3 0.763680 0.370698 0.210115 21.00000 0.02485 0.02366 = 0.02116 -0.00299 0.00952 -0.00407 F38 6 0.794300 0.313818 0.273477 21.00000 0.03826 0.02845 = 0.02741 0.00381 0.00882 0.00435 F39 6 0.640699 0.387108 0.193094 21.00000 0.02170 0.04647 = 0.05105 -0.01471 -0.00069 0.00180 F40 6 0.798886 0.346874 0.128592 21.00000 0.04803 0.06035 = 0.02840 -0.00741 0.01650 -0.00767 F41 6 0.828766 0.442330 0.245197 21.00000 0.02846 0.03300 = 0.06130 -0.01348 -0.00119 0.00215 PART 2 -21 B37B 3 0.778673 0.377136 0.200462 -21.00000 0.01975 0.02830 = 0.02813 0.01238 0.00646 0.00187 F38B 6 0.776238 0.311875 0.262660 -21.00000 0.11609 0.04188 = 0.03980 0.00459 0.00920 0.00006 F39B 6 0.652827 0.396684 0.172907 -21.00000 0.04458 0.03682 = 0.11537 -0.00611 -0.03278 0.00249 F40B 6 0.830684 0.352007 0.136203 -21.00000 0.10706 0.04853 = 0.06028 0.00241 0.04512 0.00887 F41B 6 0.834584 0.441935 0.235614 -21.00000 0.04433 0.03612 = 0.04366 0.01067 -0.00530 -0.01288 PART 0 HKLF 4 REM A19237O_014 in P2(1)/n REM wR2 = 0.1035, GooF = S = 1.030, Restrained GooF = 1.030 for all data REM R1 = 0.0418 for 5587 Fo > 4sig(Fo) and 0.0531 for all 6750 data REM 417 parameters refined using 0 restraints END WGHT 0.0408 1.2335 REM Highest difference peak 0.344, deepest hole -0.202, 1-sigma level 0.039 Q1 1 0.5628 0.4892 0.3551 11.00000 0.05 0.34 Q2 1 0.8081 0.3543 0.4793 11.00000 0.05 0.32 Q3 1 0.3261 0.3630 0.1668 11.00000 0.05 0.30 Q4 1 0.3718 0.3659 0.2507 11.00000 0.05 0.28 Q5 1 0.0980 0.3964 0.4150 11.00000 0.05 0.27 Q6 1 0.4993 0.2715 0.3792 11.00000 0.05 0.27 Q7 1 0.3268 0.4095 0.3161 11.00000 0.05 0.25 Q8 1 0.6047 0.3006 0.4047 11.00000 0.05 0.25 Q9 1 0.9098 0.3796 0.5158 11.00000 0.05 0.25 Q10 1 0.5890 0.5520 0.3174 11.00000 0.05 0.25 Q11 1 0.4834 0.2024 0.3594 11.00000 0.05 0.24 Q12 1 0.4769 0.6187 0.3788 11.00000 0.05 0.24 Q13 1 0.7039 0.3278 0.4445 11.00000 0.05 0.24 Q14 1 0.6405 0.4421 0.3956 11.00000 0.05 0.24 Q15 1 0.2402 0.3669 0.0986 11.00000 0.05 0.24 Q16 1 0.7318 0.3928 0.4248 11.00000 0.05 0.22 Q17 1 0.4386 0.6586 0.3017 11.00000 0.05 0.22 Q18 1 0.1968 0.3947 0.2631 11.00000 0.05 0.22 Q19 1 0.3407 0.1193 0.3173 11.00000 0.05 0.22 Q20 1 0.0854 0.3085 0.3768 11.00000 0.05 0.21 ; _shelx_res_checksum 28816 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -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 N1 N 0.50458(9) 0.38387(6) 0.35353(6) 0.01765(19) Uani 1 1 d . . . . . C2 C 0.53902(10) 0.30935(7) 0.38729(7) 0.0183(2) Uani 1 1 d . . . . . C3 C 0.65583(11) 0.29779(7) 0.43612(8) 0.0197(2) Uani 1 1 d . . . . . H3 H 0.679293 0.245751 0.458417 0.024 Uiso 1 1 calc R U . . . C4 C 0.74058(10) 0.36049(7) 0.45369(7) 0.0188(2) Uani 1 1 d . . . . . C5 C 0.70020(11) 0.43584(7) 0.42131(8) 0.0198(2) Uani 1 1 d . . . . . H5 H 0.754242 0.480366 0.433639 0.024 Uiso 1 1 calc R U . . . C6 C 0.58365(11) 0.44752(7) 0.37175(7) 0.0188(2) Uani 1 1 d . . . . . C7 C 0.86594(10) 0.34715(7) 0.50552(8) 0.0210(2) Uani 1 1 d . . . . . C8 C 0.92157(11) 0.27180(8) 0.50667(9) 0.0259(3) Uani 1 1 d . . . . . H8 H 0.878531 0.228652 0.474033 0.031 Uiso 1 1 calc R U . . . C9 C 1.03960(12) 0.25966(9) 0.55536(10) 0.0328(3) Uani 1 1 d . . . . . H9 H 1.076928 0.208334 0.555671 0.039 Uiso 1 1 calc R U . . . C10 C 1.10297(12) 0.32221(10) 0.60345(10) 0.0340(3) Uani 1 1 d . . . . . H10 H 1.183759 0.313746 0.636316 0.041 Uiso 1 1 calc R U . . . C11 C 1.04851(12) 0.39714(9) 0.60361(9) 0.0317(3) Uani 1 1 d . . . . . H11 H 1.091633 0.439838 0.637049 0.038 Uiso 1 1 calc R U . . . C12 C 0.93050(12) 0.40968(8) 0.55467(9) 0.0264(3) Uani 1 1 d . . . . . H12 H 0.893567 0.461110 0.554680 0.032 Uiso 1 1 calc R U . . . C13 C 0.45283(11) 0.23991(7) 0.37271(8) 0.0200(2) Uani 1 1 d . . . . . C14 C 0.36063(12) 0.23083(8) 0.42317(9) 0.0257(3) Uani 1 1 d . . . . . H14 H 0.347971 0.270937 0.465006 0.031 Uiso 1 1 calc R U . . . C15 C 0.28708(13) 0.16247(8) 0.41183(10) 0.0330(3) Uani 1 1 d . . . . . H15 H 0.223523 0.156124 0.445696 0.040 Uiso 1 1 calc R U . . . C16 C 0.30616(14) 0.10391(8) 0.35159(10) 0.0346(3) Uani 1 1 d . . . . . H16 H 0.254663 0.057905 0.343290 0.041 Uiso 1 1 calc R U . . . C17 C 0.39994(15) 0.11193(8) 0.30326(9) 0.0338(3) Uani 1 1 d . . . . . H17 H 0.413470 0.071051 0.262566 0.041 Uiso 1 1 calc R U . . . C18 C 0.47430(13) 0.17950(8) 0.31406(8) 0.0268(3) Uani 1 1 d . . . . . H18 H 0.539590 0.184580 0.281593 0.032 Uiso 1 1 calc R U . . . C19 C 0.54573(11) 0.52992(7) 0.33956(8) 0.0202(2) Uani 1 1 d . . . . . C20 C 0.46270(13) 0.57335(8) 0.37910(9) 0.0286(3) Uani 1 1 d . . . . . H20 H 0.424867 0.549286 0.423875 0.034 Uiso 1 1 calc R U . . . C21 C 0.43521(15) 0.65210(8) 0.35292(10) 0.0360(3) Uani 1 1 d . . . . . H21 H 0.377927 0.681789 0.379438 0.043 Uiso 1 1 calc R U . . . C22 C 0.49105(15) 0.68724(8) 0.28842(10) 0.0389(3) Uani 1 1 d . . . . . H22 H 0.472622 0.741245 0.271019 0.047 Uiso 1 1 calc R U . . . C23 C 0.57351(15) 0.64420(9) 0.24914(11) 0.0386(3) Uani 1 1 d . . . . . H23 H 0.611352 0.668724 0.204642 0.046 Uiso 1 1 calc R U . . . C24 C 0.60167(13) 0.56526(8) 0.27416(9) 0.0297(3) Uani 1 1 d . . . . . H24 H 0.658434 0.535721 0.246973 0.036 Uiso 1 1 calc R U . . . C25 C 0.38268(10) 0.39604(7) 0.29312(7) 0.0186(2) Uani 1 1 d . . . . . H25 H 0.385405 0.451574 0.268717 0.022 Uiso 1 1 calc R U . . . C26 C 0.36032(11) 0.34028(7) 0.21019(8) 0.0213(2) Uani 1 1 d . . . . . H26A H 0.440202 0.319218 0.199837 0.026 Uiso 1 1 calc R U . . . H26B H 0.309443 0.294126 0.222185 0.026 Uiso 1 1 calc R U . . . C27 C 0.29606(11) 0.38352(7) 0.12639(8) 0.0205(2) Uani 1 1 d . . . . . C28 C 0.16906(12) 0.37795(7) 0.09756(8) 0.0240(2) Uani 1 1 d . . . . . H28 H 0.120978 0.347773 0.131515 0.029 Uiso 1 1 calc R U . . . C29 C 0.11228(12) 0.41645(8) 0.01914(9) 0.0291(3) Uani 1 1 d . . . . . H29 H 0.025704 0.412502 0.000093 0.035 Uiso 1 1 calc R U . . . C30 C 0.18120(14) 0.46026(8) -0.03095(9) 0.0320(3) Uani 1 1 d . . . . . H30 H 0.142310 0.486102 -0.084537 0.038 Uiso 1 1 calc R U . . . C31 C 0.30737(14) 0.46636(9) -0.00270(9) 0.0328(3) Uani 1 1 d . . . . . H31 H 0.354999 0.496550 -0.036971 0.039 Uiso 1 1 calc R U . . . C32 C 0.36461(12) 0.42840(8) 0.07575(9) 0.0268(3) Uani 1 1 d . . . . . H32 H 0.451067 0.433156 0.094873 0.032 Uiso 1 1 calc R U . . . C33 C 0.28369(11) 0.39812(7) 0.35152(8) 0.0213(2) Uani 1 1 d . . . . . O34 O 0.30210(8) 0.42346(6) 0.42705(6) 0.0300(2) Uani 1 1 d . . . . . O35 O 0.17668(8) 0.37198(6) 0.30715(6) 0.0281(2) Uani 1 1 d . . . . . C36 C 0.07537(13) 0.37271(11) 0.35645(10) 0.0387(4) Uani 1 1 d . . . . . H36A H 0.008651 0.338522 0.325675 0.058 Uiso 1 1 calc R U . . . H36B H 0.045143 0.427683 0.359506 0.058 Uiso 1 1 calc R U . . . H36C H 0.104215 0.352398 0.417319 0.058 Uiso 1 1 calc R U . . . B37 B 0.7637(15) 0.3707(8) 0.2101(10) 0.023(2) Uani 0.60(3) 1 d . . P A 1 F38 F 0.7943(5) 0.3138(4) 0.2735(4) 0.0310(11) Uani 0.60(3) 1 d . . P A 1 F39 F 0.6407(6) 0.3871(5) 0.1931(4) 0.0407(12) Uani 0.60(3) 1 d . . P A 1 F40 F 0.7989(6) 0.3469(5) 0.1286(5) 0.0444(10) Uani 0.60(3) 1 d . . P A 1 F41 F 0.8288(10) 0.4423(6) 0.2452(8) 0.0421(17) Uani 0.60(3) 1 d . . P A 1 B37B B 0.779(2) 0.3771(14) 0.2005(15) 0.025(3) Uani 0.40(3) 1 d . . P A 2 F38B F 0.7762(16) 0.3119(7) 0.2627(10) 0.067(3) Uani 0.40(3) 1 d . . P A 2 F39B F 0.6528(15) 0.3967(9) 0.1729(17) 0.072(3) Uani 0.40(3) 1 d . . P A 2 F40B F 0.831(2) 0.3520(9) 0.1362(10) 0.068(3) Uani 0.40(3) 1 d . . P A 2 F41B F 0.8346(16) 0.4419(9) 0.2356(12) 0.043(3) Uani 0.40(3) 1 d . . 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 N1 0.0193(5) 0.0161(4) 0.0166(4) 0.0013(3) 0.0009(3) -0.0010(4) C2 0.0221(5) 0.0165(5) 0.0163(5) 0.0011(4) 0.0037(4) -0.0008(4) C3 0.0222(5) 0.0167(5) 0.0198(5) 0.0033(4) 0.0026(4) 0.0003(4) C4 0.0195(5) 0.0210(6) 0.0161(5) 0.0014(4) 0.0038(4) -0.0010(4) C5 0.0219(5) 0.0177(5) 0.0193(5) -0.0003(4) 0.0029(4) -0.0031(4) C6 0.0223(5) 0.0162(5) 0.0178(5) 0.0001(4) 0.0038(4) -0.0010(4) C7 0.0189(5) 0.0241(6) 0.0198(5) 0.0049(4) 0.0030(4) -0.0017(4) C8 0.0239(6) 0.0242(6) 0.0289(6) 0.0054(5) 0.0034(5) 0.0004(5) C9 0.0259(6) 0.0344(7) 0.0377(7) 0.0118(6) 0.0052(5) 0.0064(5) C10 0.0201(6) 0.0485(9) 0.0314(7) 0.0125(6) -0.0004(5) -0.0001(6) C11 0.0248(6) 0.0407(8) 0.0275(6) 0.0034(6) -0.0007(5) -0.0087(6) C12 0.0241(6) 0.0280(6) 0.0261(6) 0.0019(5) 0.0022(5) -0.0030(5) C13 0.0212(5) 0.0169(5) 0.0197(5) 0.0041(4) -0.0021(4) -0.0022(4) C14 0.0260(6) 0.0213(6) 0.0297(6) 0.0037(5) 0.0047(5) -0.0006(5) C15 0.0269(6) 0.0303(7) 0.0414(8) 0.0088(6) 0.0050(6) -0.0062(5) C16 0.0377(7) 0.0252(7) 0.0353(7) 0.0062(6) -0.0077(6) -0.0139(6) C17 0.0523(9) 0.0211(6) 0.0250(6) -0.0019(5) -0.0005(6) -0.0083(6) C18 0.0365(7) 0.0218(6) 0.0218(6) 0.0013(5) 0.0044(5) -0.0032(5) C19 0.0232(6) 0.0145(5) 0.0208(5) 0.0007(4) -0.0016(4) -0.0018(4) C20 0.0410(7) 0.0212(6) 0.0245(6) 0.0018(5) 0.0080(5) 0.0031(5) C21 0.0531(9) 0.0225(6) 0.0329(7) 0.0003(5) 0.0093(6) 0.0117(6) C22 0.0560(9) 0.0183(6) 0.0416(8) 0.0081(6) 0.0073(7) 0.0061(6) C23 0.0490(9) 0.0253(7) 0.0439(8) 0.0136(6) 0.0149(7) -0.0013(6) C24 0.0317(7) 0.0225(6) 0.0362(7) 0.0058(5) 0.0100(5) 0.0003(5) C25 0.0193(5) 0.0166(5) 0.0180(5) 0.0008(4) -0.0017(4) 0.0008(4) C26 0.0247(6) 0.0193(5) 0.0182(5) -0.0006(4) -0.0004(4) 0.0025(4) C27 0.0259(6) 0.0167(5) 0.0172(5) -0.0027(4) -0.0001(4) 0.0030(4) C28 0.0269(6) 0.0210(6) 0.0223(6) -0.0020(5) -0.0005(5) -0.0021(5) C29 0.0291(6) 0.0256(6) 0.0276(6) -0.0041(5) -0.0078(5) 0.0016(5) C30 0.0435(8) 0.0281(7) 0.0203(6) 0.0027(5) -0.0051(5) 0.0055(6) C31 0.0411(8) 0.0317(7) 0.0263(7) 0.0070(5) 0.0077(6) 0.0010(6) C32 0.0250(6) 0.0289(6) 0.0261(6) 0.0012(5) 0.0036(5) 0.0031(5) C33 0.0221(6) 0.0177(5) 0.0227(6) -0.0002(4) 0.0005(4) 0.0012(4) O34 0.0286(5) 0.0361(5) 0.0249(5) -0.0091(4) 0.0041(4) -0.0031(4) O35 0.0201(4) 0.0382(5) 0.0249(4) -0.0055(4) 0.0015(3) -0.0017(4) C36 0.0219(6) 0.0566(10) 0.0390(8) -0.0154(7) 0.0088(6) -0.0052(6) B37 0.025(3) 0.024(3) 0.021(3) -0.003(3) 0.010(2) -0.0041(19) F38 0.038(2) 0.0284(15) 0.0274(15) 0.0038(10) 0.0088(10) 0.0044(9) F39 0.0217(12) 0.046(3) 0.051(2) -0.0147(15) -0.0007(12) 0.0018(13) F40 0.048(2) 0.0603(19) 0.0284(15) -0.0074(10) 0.0165(12) -0.0077(13) F41 0.028(2) 0.033(3) 0.061(4) -0.013(2) -0.001(2) 0.002(2) B37B 0.020(5) 0.028(4) 0.028(5) 0.012(3) 0.006(4) 0.002(4) F38B 0.116(7) 0.042(3) 0.040(3) 0.005(2) 0.009(4) 0.000(4) F39B 0.045(4) 0.037(2) 0.115(8) -0.006(5) -0.033(4) 0.002(3) F40B 0.107(9) 0.049(3) 0.060(4) 0.002(3) 0.045(5) 0.009(5) F41B 0.044(5) 0.036(5) 0.044(3) 0.011(3) -0.005(3) -0.013(4) 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 120.25(10) . . ? C6 N1 C25 119.16(9) . . ? C2 N1 C25 120.54(9) . . ? N1 C2 C3 119.71(10) . . ? N1 C2 C13 121.53(10) . . ? C3 C2 C13 118.76(10) . . ? C2 C3 C4 121.80(11) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C5 C4 C3 116.62(10) . . ? C5 C4 C7 122.10(10) . . ? C3 C4 C7 121.27(10) . . ? C6 C5 C4 121.72(11) . . ? C6 C5 H5 119.1 . . ? C4 C5 H5 119.1 . . ? N1 C6 C5 119.81(10) . . ? N1 C6 C19 121.12(10) . . ? C5 C6 C19 119.07(10) . . ? C8 C7 C12 118.91(11) . . ? C8 C7 C4 120.60(11) . . ? C12 C7 C4 120.49(11) . . ? C9 C8 C7 120.35(12) . . ? C9 C8 H8 119.8 . . ? C7 C8 H8 119.8 . . ? C10 C9 C8 120.24(13) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.07(12) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C12 119.91(13) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C11 C12 C7 120.53(13) . . ? C11 C12 H12 119.7 . . ? C7 C12 H12 119.7 . . ? C14 C13 C18 120.08(11) . . ? C14 C13 C2 121.09(11) . . ? C18 C13 C2 118.49(11) . . ? C13 C14 C15 119.45(12) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.25(13) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C17 120.27(12) . . ? C15 C16 H16 119.9 . . ? C17 C16 H16 119.9 . . ? C16 C17 C18 120.17(13) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 119.72(13) . . ? C17 C18 H18 120.1 . . ? C13 C18 H18 120.1 . . ? C20 C19 C24 120.17(11) . . ? C20 C19 C6 120.46(11) . . ? C24 C19 C6 119.18(11) . . ? C21 C20 C19 119.77(12) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 C20 120.07(13) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C23 C22 C21 120.21(13) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.52(13) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? C23 C24 C19 119.25(13) . . ? C23 C24 H24 120.4 . . ? C19 C24 H24 120.4 . . ? N1 C25 C33 107.95(9) . . ? N1 C25 C26 114.01(9) . . ? C33 C25 C26 117.40(10) . . ? N1 C25 H25 105.5 . . ? C33 C25 H25 105.5 . . ? C26 C25 H25 105.5 . . ? C27 C26 C25 112.03(9) . . ? C27 C26 H26A 109.2 . . ? C25 C26 H26A 109.2 . . ? C27 C26 H26B 109.2 . . ? C25 C26 H26B 109.2 . . ? H26A C26 H26B 107.9 . . ? C32 C27 C28 118.81(11) . . ? C32 C27 C26 119.90(11) . . ? C28 C27 C26 121.27(11) . . ? C29 C28 C27 120.35(12) . . ? C29 C28 H28 119.8 . . ? C27 C28 H28 119.8 . . ? C30 C29 C28 120.37(12) . . ? C30 C29 H29 119.8 . . ? C28 C29 H29 119.8 . . ? C29 C30 C31 119.70(12) . . ? C29 C30 H30 120.2 . . ? C31 C30 H30 120.2 . . ? C30 C31 C32 120.25(13) . . ? C30 C31 H31 119.9 . . ? C32 C31 H31 119.9 . . ? C31 C32 C27 120.51(12) . . ? C31 C32 H32 119.7 . . ? C27 C32 H32 119.7 . . ? O34 C33 O35 125.37(11) . . ? O34 C33 C25 123.09(11) . . ? O35 C33 C25 111.49(10) . . ? C33 O35 C36 115.88(10) . . ? O35 C36 H36A 109.5 . . ? O35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? O35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? F38 B37 F39 112.7(12) . . ? F38 B37 F40 110.5(10) . . ? F39 B37 F40 108.4(10) . . ? F38 B37 F41 106.1(10) . . ? F39 B37 F41 108.4(10) . . ? F40 B37 F41 110.7(12) . . ? F40B B37B F41B 109(2) . . ? F40B B37B F39B 113.8(17) . . ? F41B B37B F39B 107.2(17) . . ? F40B B37B F38B 108.3(17) . . ? F41B B37B F38B 114.9(18) . . ? F39B B37B F38B 103.3(17) . . ? 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 N1 C6 1.3708(14) . ? N1 C2 1.3711(14) . ? N1 C25 1.4975(14) . ? C2 C3 1.3790(16) . ? C2 C13 1.4903(16) . ? C3 C4 1.3969(16) . ? C3 H3 0.9500 . ? C4 C5 1.3924(16) . ? C4 C7 1.4790(16) . ? C5 C6 1.3810(16) . ? C5 H5 0.9500 . ? C6 C19 1.4924(16) . ? C7 C8 1.3980(17) . ? C7 C12 1.3989(17) . ? C8 C9 1.3909(18) . ? C8 H8 0.9500 . ? C9 C10 1.387(2) . ? C9 H9 0.9500 . ? C10 C11 1.388(2) . ? C10 H10 0.9500 . ? C11 C12 1.3931(18) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.3918(17) . ? C13 C18 1.3932(17) . ? C14 C15 1.3927(18) . ? C14 H14 0.9500 . ? C15 C16 1.380(2) . ? C15 H15 0.9500 . ? C16 C17 1.383(2) . ? C16 H16 0.9500 . ? C17 C18 1.3870(18) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 C20 1.3898(18) . ? C19 C24 1.3933(17) . ? C20 C21 1.3894(18) . ? C20 H20 0.9500 . ? C21 C22 1.380(2) . ? C21 H21 0.9500 . ? C22 C23 1.379(2) . ? C22 H22 0.9500 . ? C23 C24 1.3895(19) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C33 1.5307(17) . ? C25 C26 1.5471(16) . ? C25 H25 1.0000 . ? C26 C27 1.5191(16) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C32 1.3929(18) . ? C27 C28 1.3952(17) . ? C28 C29 1.3951(17) . ? C28 H28 0.9500 . ? C29 C30 1.381(2) . ? C29 H29 0.9500 . ? C30 C31 1.386(2) . ? C30 H30 0.9500 . ? C31 C32 1.3927(18) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 O34 1.2028(15) . ? C33 O35 1.3229(14) . ? O35 C36 1.4575(16) . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? B37 F38 1.348(17) . ? B37 F39 1.365(18) . ? B37 F40 1.420(16) . ? B37 F41 1.445(18) . ? B37B F40B 1.29(3) . ? B37B F41B 1.31(3) . ? B37B F39B 1.42(3) . ? B37B F38B 1.44(3) . ? 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 C6 N1 C2 C3 -3.12(16) . . . . ? C25 N1 C2 C3 174.17(10) . . . . ? C6 N1 C2 C13 176.74(10) . . . . ? C25 N1 C2 C13 -5.97(16) . . . . ? N1 C2 C3 C4 1.01(17) . . . . ? C13 C2 C3 C4 -178.86(11) . . . . ? C2 C3 C4 C5 1.56(17) . . . . ? C2 C3 C4 C7 -179.49(11) . . . . ? C3 C4 C5 C6 -2.11(17) . . . . ? C7 C4 C5 C6 178.95(11) . . . . ? C2 N1 C6 C5 2.58(16) . . . . ? C25 N1 C6 C5 -174.74(10) . . . . ? C2 N1 C6 C19 -176.88(10) . . . . ? C25 N1 C6 C19 5.79(16) . . . . ? C4 C5 C6 N1 0.09(17) . . . . ? C4 C5 C6 C19 179.57(10) . . . . ? C5 C4 C7 C8 -154.29(11) . . . . ? C3 C4 C7 C8 26.81(17) . . . . ? C5 C4 C7 C12 26.11(17) . . . . ? C3 C4 C7 C12 -152.79(12) . . . . ? C12 C7 C8 C9 -0.55(18) . . . . ? C4 C7 C8 C9 179.84(11) . . . . ? C7 C8 C9 C10 0.2(2) . . . . ? C8 C9 C10 C11 0.4(2) . . . . ? C9 C10 C11 C12 -0.6(2) . . . . ? C10 C11 C12 C7 0.3(2) . . . . ? C8 C7 C12 C11 0.30(18) . . . . ? C4 C7 C12 C11 179.91(11) . . . . ? N1 C2 C13 C14 -78.36(15) . . . . ? C3 C2 C13 C14 101.51(14) . . . . ? N1 C2 C13 C18 108.34(13) . . . . ? C3 C2 C13 C18 -71.79(15) . . . . ? C18 C13 C14 C15 -2.56(18) . . . . ? C2 C13 C14 C15 -175.75(11) . . . . ? C13 C14 C15 C16 0.5(2) . . . . ? C14 C15 C16 C17 1.2(2) . . . . ? C15 C16 C17 C18 -1.0(2) . . . . ? C16 C17 C18 C13 -1.1(2) . . . . ? C14 C13 C18 C17 2.82(18) . . . . ? C2 C13 C18 C17 176.19(11) . . . . ? N1 C6 C19 C20 72.73(15) . . . . ? C5 C6 C19 C20 -106.74(14) . . . . ? N1 C6 C19 C24 -112.23(13) . . . . ? C5 C6 C19 C24 68.30(15) . . . . ? C24 C19 C20 C21 0.3(2) . . . . ? C6 C19 C20 C21 175.27(12) . . . . ? C19 C20 C21 C22 -0.6(2) . . . . ? C20 C21 C22 C23 0.5(2) . . . . ? C21 C22 C23 C24 -0.2(2) . . . . ? C22 C23 C24 C19 -0.1(2) . . . . ? C20 C19 C24 C23 0.0(2) . . . . ? C6 C19 C24 C23 -175.02(13) . . . . ? C6 N1 C25 C33 -104.88(11) . . . . ? C2 N1 C25 C33 77.80(12) . . . . ? C6 N1 C25 C26 122.75(11) . . . . ? C2 N1 C25 C26 -54.57(14) . . . . ? N1 C25 C26 C27 -140.47(10) . . . . ? C33 C25 C26 C27 91.87(12) . . . . ? C25 C26 C27 C32 84.06(13) . . . . ? C25 C26 C27 C28 -97.31(13) . . . . ? C32 C27 C28 C29 0.30(18) . . . . ? C26 C27 C28 C29 -178.34(11) . . . . ? C27 C28 C29 C30 0.22(19) . . . . ? C28 C29 C30 C31 -0.4(2) . . . . ? C29 C30 C31 C32 0.1(2) . . . . ? C30 C31 C32 C27 0.4(2) . . . . ? C28 C27 C32 C31 -0.61(19) . . . . ? C26 C27 C32 C31 178.05(12) . . . . ? N1 C25 C33 O34 31.64(15) . . . . ? C26 C25 C33 O34 162.16(11) . . . . ? N1 C25 C33 O35 -150.93(10) . . . . ? C26 C25 C33 O35 -20.41(14) . . . . ? O34 C33 O35 C36 -1.73(19) . . . . ? C25 C33 O35 C36 -179.08(11) . . . . ?