#------------------------------------------------------------------------------ #$Date: 2020-04-05 13:35:19 +0300 (Sun, 05 Apr 2020) $ #$Revision: 250256 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/74/1557435.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_1557435 loop_ _publ_author_name 'Williams, Alexander F.' 'White, Andrew J. P.' 'Spivey, Alan C.' 'Cordier, Christopher J.' _publ_section_title ; meta-Selective C--H functionalisation of aryl boronic acids directed by a MIDA-derived boronate ester ; _journal_issue 12 _journal_name_full 'Chemical Science' _journal_page_first 3301 _journal_paper_doi 10.1039/D0SC00230E _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C20 H19 B N2 O5' _chemical_formula_sum 'C20 H19 B N2 O5' _chemical_formula_weight 378.18 _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 _audit_creation_method SHELXL-2017/1 _audit_update_record ; 2019-10-24 deposited with the CCDC. 2020-03-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.222(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.8085(5) _cell_length_b 8.9262(4) _cell_length_c 21.7277(9) _cell_measurement_reflns_used 1537 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.0550 _cell_measurement_theta_min 3.1100 _cell_volume 1877.73(15) _computing_cell_refinement 'CrysAlisPro, Rigaku OD' _computing_data_collection 'CrysAlisPro, Rigaku OD' _computing_data_reduction 'CrysAlisPro, Rigaku OD' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CIFTAB-2014 (Sheldrick, 2017)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXS-2014 (Sheldrick, 2017)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 16.0382 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.805 _diffrn_measurement_device_type 'Agilent Xcalibur 3 E' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_unetI/netI 0.0457 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.805 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 6389 _diffrn_reflns_point_group_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.805 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.211 _diffrn_reflns_theta_min 2.471 _diffrn_source 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_correction_T_min 0.954 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.338 _exptl_crystal_description 'blocky needles' _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.756 _exptl_crystal_size_mid 0.225 _exptl_crystal_size_min 0.125 _refine_diff_density_max 0.239 _refine_diff_density_min -0.203 _refine_diff_density_rms 0.041 _refine_ls_extinction_coef 0.0068(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2017/1 (Sheldrick 2017)' _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 254 _refine_ls_number_reflns 3720 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all 0.0648 _refine_ls_R_factor_gt 0.0439 _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^)+(0.0386P)^2^+0.2745P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0895 _refine_ls_wR_factor_ref 0.1012 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2805 _reflns_number_total 3720 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00230e2.cif _cod_data_source_block 7 _cod_depositor_comments 'Adding full bibliography for 1557435.cif.' _cod_original_cell_volume 1877.72(16) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1557435 _shelx_shelxl_version_number 2017/1 _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_res_file ; TITL CJC1801 in P2(1)/c CJC1801.res created by SHELXL-2017/1 at 13:28:49 on 16-Nov-2018 REM P2(1)/c (#14 in standard setting) REM AFW-4-138 CELL 0.71073 9.808452 8.926230 21.727692 90.0000 99.2223 90.0000 ZERR 4.00 0.000514 0.000433 0.000901 0.0000 0.0052 0.0000 LATT 1 SYMM -x, y+1/2,-z+1/2 SFAC C H B N O UNIT 80 76 4 8 20 TEMP -100 L.S. 6 FMAP 2 PLAN 10 ACTA WGHT 0.038600 0.274500 EXTI 0.006799 FVAR 6.45241 N1 4 0.466532 0.134752 0.351577 11.00000 0.02344 0.02055 = 0.01794 0.00117 0.00426 0.00026 C2 1 0.398658 0.059691 0.400311 11.00000 0.03008 0.02559 = 0.02302 0.00378 0.00825 0.00155 AFIX 23 H2A 2 0.300760 0.037238 0.383843 11.00000 -1.20000 H2B 2 0.402398 0.124843 0.437418 11.00000 -1.20000 AFIX 0 C3 1 0.478163 -0.082887 0.416959 11.00000 0.03286 0.02226 = 0.02886 0.00004 0.00478 -0.00240 O3 5 0.472951 -0.157327 0.462665 11.00000 0.04892 0.02778 = 0.03296 0.00965 0.00926 0.00116 O4 5 0.555345 -0.117409 0.373703 11.00000 0.03849 0.02244 = 0.03513 0.00339 0.01386 0.00537 C5 1 0.364642 0.187900 0.297686 11.00000 0.02486 0.02915 = 0.02067 0.00337 0.00150 0.00133 AFIX 23 H5A 2 0.402487 0.273229 0.276700 11.00000 -1.20000 H5B 2 0.277892 0.220003 0.311607 11.00000 -1.20000 AFIX 0 C6 1 0.339052 0.054913 0.254222 11.00000 0.02528 0.03680 = 0.02459 -0.00215 0.00803 -0.00501 O6 5 0.249203 0.047528 0.209632 11.00000 0.03114 0.06260 = 0.02964 -0.01044 -0.00258 -0.00552 O7 5 0.431538 -0.052056 0.271002 11.00000 0.02868 0.02985 = 0.03224 -0.00906 0.00504 -0.00281 B8 3 0.543132 -0.009161 0.322600 11.00000 0.03006 0.01923 = 0.02395 -0.00407 0.00470 0.00228 C9 1 0.565610 0.254265 0.378919 11.00000 0.02448 0.02104 = 0.02198 -0.00202 0.00375 -0.00114 AFIX 23 H9A 2 0.619750 0.287744 0.346713 11.00000 -1.20000 H9B 2 0.631038 0.210541 0.413710 11.00000 -1.20000 AFIX 0 C10 1 0.496548 0.389905 0.402967 11.00000 0.02802 0.02330 = 0.02459 -0.00159 0.00313 0.00421 AFIX 23 H10A 2 0.429431 0.433156 0.368684 11.00000 -1.20000 H10B 2 0.445153 0.358094 0.436408 11.00000 -1.20000 AFIX 0 C11 1 0.600954 0.507718 0.428041 11.00000 0.03515 0.02160 = 0.02251 -0.00018 0.00236 0.00296 AFIX 23 H11A 2 0.652156 0.542301 0.394952 11.00000 -1.20000 H11B 2 0.554461 0.594963 0.443709 11.00000 -1.20000 AFIX 0 O12 5 0.693401 0.438445 0.477881 11.00000 0.03262 0.02247 = 0.02734 0.00140 -0.00349 -0.00146 C13 1 0.792678 0.523453 0.511905 11.00000 0.02698 0.02916 = 0.02393 -0.00679 0.00941 -0.00394 C14 1 0.885218 0.445830 0.556300 11.00000 0.02762 0.03784 = 0.02357 -0.00198 0.00851 -0.00192 C15 1 0.988919 0.522187 0.594836 11.00000 0.02992 0.06115 = 0.03056 -0.00482 0.00323 -0.00360 AFIX 43 H15A 2 1.051878 0.468848 0.624778 11.00000 -1.20000 AFIX 0 C16 1 1.000546 0.675533 0.589650 11.00000 0.03419 0.05652 = 0.04853 -0.02364 0.00922 -0.01268 AFIX 43 H16A 2 1.070624 0.728259 0.616341 11.00000 -1.20000 AFIX 0 C17 1 0.910052 0.751677 0.545593 11.00000 0.03800 0.03428 = 0.05884 -0.01932 0.02017 -0.00831 AFIX 43 H17A 2 0.918792 0.857201 0.542083 11.00000 -1.20000 AFIX 0 C18 1 0.806241 0.677628 0.506157 11.00000 0.03029 0.02631 = 0.04297 -0.00644 0.01094 -0.00045 AFIX 43 H18A 2 0.745273 0.731632 0.475641 11.00000 -1.20000 AFIX 0 C19 1 0.872095 0.285692 0.561445 11.00000 0.02873 0.04511 = 0.02890 0.00782 0.00279 0.00128 N20 4 0.863043 0.159165 0.567265 11.00000 0.04805 0.04473 = 0.05752 0.01817 0.00161 0.00189 C21 1 0.683941 0.023672 0.298510 11.00000 0.02822 0.02103 = 0.02526 -0.00655 0.00640 0.00215 C22 1 0.685591 0.106862 0.244315 11.00000 0.03367 0.03321 = 0.03014 -0.00317 0.00916 0.00503 AFIX 43 H22A 2 0.600940 0.144106 0.222228 11.00000 -1.20000 AFIX 0 C23 1 0.806860 0.136723 0.221787 11.00000 0.04587 0.05436 = 0.03598 0.00320 0.01862 0.00014 AFIX 43 H23A 2 0.805197 0.195834 0.185315 11.00000 -1.20000 AFIX 0 C24 1 0.929783 0.080627 0.252323 11.00000 0.03291 0.07717 = 0.04748 -0.00792 0.02071 -0.00234 AFIX 43 H24A 2 1.013273 0.099953 0.236808 11.00000 -1.20000 AFIX 0 C25 1 0.931445 -0.003308 0.305246 11.00000 0.02831 0.06949 = 0.04566 -0.00519 0.00397 0.00877 AFIX 43 H25A 2 1.016281 -0.042944 0.326133 11.00000 -1.20000 AFIX 0 C26 1 0.810151 -0.030846 0.328558 11.00000 0.03326 0.04252 = 0.03175 -0.00245 0.00455 0.00402 AFIX 43 H26A 2 0.813327 -0.087899 0.365670 11.00000 -1.20000 AFIX 0 HKLF 4 REM CJC1801 in P2(1)/c REM R1 = 0.0439 for 2805 Fo > 4sig(Fo) and 0.0648 for all 3720 data REM 254 parameters refined using 0 restraints END WGHT 0.0386 0.2754 REM Highest difference peak 0.239, deepest hole -0.203, 1-sigma level 0.041 Q1 1 0.6158 0.0140 0.3086 11.00000 0.05 0.24 Q2 1 0.5309 0.3220 0.3910 11.00000 0.05 0.18 Q3 1 0.5127 0.0623 0.3373 11.00000 0.05 0.17 Q4 1 0.7751 0.6004 0.5258 11.00000 0.05 0.17 Q5 1 0.8202 0.5929 0.4976 11.00000 0.05 0.16 Q6 1 0.2671 0.0416 0.4269 11.00000 0.05 0.16 Q7 1 0.8667 0.4731 0.5243 11.00000 0.05 0.15 Q8 1 1.0154 -0.1247 0.3444 11.00000 0.05 0.15 Q9 1 0.4480 0.0000 0.4200 11.00000 0.05 0.15 Q10 1 0.6253 -0.2195 0.3668 11.00000 0.05 0.14 ; _shelx_res_checksum 16659 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 N1 N 0.46653(12) 0.13475(14) 0.35158(5) 0.0205(3) Uani 1 1 d . . . . . C2 C 0.39866(17) 0.05969(17) 0.40031(7) 0.0258(4) Uani 1 1 d . . . . . H2A H 0.300760 0.037238 0.383843 0.031 Uiso 1 1 calc R U . . . H2B H 0.402398 0.124843 0.437418 0.031 Uiso 1 1 calc R U . . . C3 C 0.47816(17) -0.08289(18) 0.41696(8) 0.0280(4) Uani 1 1 d . . . . . O3 O 0.47295(13) -0.15733(13) 0.46266(5) 0.0363(3) Uani 1 1 d . . . . . O4 O 0.55534(12) -0.11741(12) 0.37370(5) 0.0311(3) Uani 1 1 d . . . . . C5 C 0.36464(16) 0.18790(18) 0.29769(7) 0.0251(4) Uani 1 1 d . . . . . H5A H 0.402487 0.273229 0.276700 0.030 Uiso 1 1 calc R U . . . H5B H 0.277892 0.220003 0.311607 0.030 Uiso 1 1 calc R U . . . C6 C 0.33905(17) 0.0549(2) 0.25422(7) 0.0284(4) Uani 1 1 d . . . . . O6 O 0.24920(12) 0.04753(15) 0.20963(5) 0.0419(3) Uani 1 1 d . . . . . O7 O 0.43154(11) -0.05206(12) 0.27100(5) 0.0302(3) Uani 1 1 d . . . . . B8 B 0.54313(19) -0.0092(2) 0.32260(8) 0.0244(4) Uani 1 1 d . . . . . C9 C 0.56561(15) 0.25427(17) 0.37892(7) 0.0225(3) Uani 1 1 d . . . . . H9A H 0.619750 0.287744 0.346713 0.027 Uiso 1 1 calc R U . . . H9B H 0.631038 0.210541 0.413710 0.027 Uiso 1 1 calc R U . . . C10 C 0.49655(16) 0.38991(17) 0.40297(7) 0.0254(4) Uani 1 1 d . . . . . H10A H 0.429431 0.433156 0.368684 0.031 Uiso 1 1 calc R U . . . H10B H 0.445153 0.358094 0.436408 0.031 Uiso 1 1 calc R U . . . C11 C 0.60095(16) 0.50772(18) 0.42804(7) 0.0267(4) Uani 1 1 d . . . . . H11A H 0.652156 0.542301 0.394952 0.032 Uiso 1 1 calc R U . . . H11B H 0.554461 0.594963 0.443709 0.032 Uiso 1 1 calc R U . . . O12 O 0.69340(11) 0.43844(12) 0.47788(5) 0.0284(3) Uani 1 1 d . . . . . C13 C 0.79268(16) 0.52345(18) 0.51190(7) 0.0261(4) Uani 1 1 d . . . . . C14 C 0.88522(17) 0.4458(2) 0.55630(7) 0.0292(4) Uani 1 1 d . . . . . C15 C 0.98892(18) 0.5222(2) 0.59484(8) 0.0407(5) Uani 1 1 d . . . . . H15A H 1.051878 0.468848 0.624778 0.049 Uiso 1 1 calc R U . . . C16 C 1.0005(2) 0.6755(2) 0.58965(9) 0.0461(5) Uani 1 1 d . . . . . H16A H 1.070624 0.728259 0.616341 0.055 Uiso 1 1 calc R U . . . C17 C 0.91005(19) 0.7517(2) 0.54559(9) 0.0423(5) Uani 1 1 d . . . . . H17A H 0.918792 0.857201 0.542083 0.051 Uiso 1 1 calc R U . . . C18 C 0.80624(17) 0.67763(19) 0.50616(8) 0.0326(4) Uani 1 1 d . . . . . H18A H 0.745273 0.731632 0.475641 0.039 Uiso 1 1 calc R U . . . C19 C 0.87209(18) 0.2857(2) 0.56145(8) 0.0344(4) Uani 1 1 d . . . . . N20 N 0.86304(17) 0.1592(2) 0.56727(8) 0.0509(5) Uani 1 1 d . . . . . C21 C 0.68394(16) 0.02367(17) 0.29851(7) 0.0246(4) Uani 1 1 d . . . . . C22 C 0.68559(18) 0.10686(19) 0.24432(8) 0.0319(4) Uani 1 1 d . . . . . H22A H 0.600940 0.144106 0.222228 0.038 Uiso 1 1 calc R U . . . C23 C 0.8069(2) 0.1367(2) 0.22179(9) 0.0441(5) Uani 1 1 d . . . . . H23A H 0.805197 0.195834 0.185315 0.053 Uiso 1 1 calc R U . . . C24 C 0.9298(2) 0.0806(3) 0.25232(9) 0.0510(6) Uani 1 1 d . . . . . H24A H 1.013273 0.099953 0.236808 0.061 Uiso 1 1 calc R U . . . C25 C 0.93145(19) -0.0033(3) 0.30525(9) 0.0480(5) Uani 1 1 d . . . . . H25A H 1.016281 -0.042944 0.326133 0.058 Uiso 1 1 calc R U . . . C26 C 0.81015(17) -0.0308(2) 0.32856(8) 0.0359(4) Uani 1 1 d . . . . . H26A H 0.813327 -0.087899 0.365670 0.043 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0234(6) 0.0206(7) 0.0179(6) 0.0012(6) 0.0043(5) 0.0003(6) C2 0.0301(8) 0.0256(8) 0.0230(8) 0.0038(7) 0.0083(7) 0.0015(8) C3 0.0329(9) 0.0223(8) 0.0289(9) 0.0000(8) 0.0048(8) -0.0024(8) O3 0.0489(8) 0.0278(6) 0.0330(7) 0.0096(6) 0.0093(6) 0.0012(6) O4 0.0385(7) 0.0224(6) 0.0351(6) 0.0034(5) 0.0139(5) 0.0054(5) C5 0.0249(8) 0.0291(9) 0.0207(8) 0.0034(7) 0.0015(7) 0.0013(7) C6 0.0253(8) 0.0368(10) 0.0246(8) -0.0022(8) 0.0080(7) -0.0050(8) O6 0.0311(6) 0.0626(9) 0.0296(6) -0.0104(6) -0.0026(6) -0.0055(6) O7 0.0287(6) 0.0298(6) 0.0322(6) -0.0091(5) 0.0050(5) -0.0028(6) B8 0.0301(9) 0.0192(9) 0.0240(9) -0.0041(8) 0.0047(8) 0.0023(8) C9 0.0245(8) 0.0210(8) 0.0220(8) -0.0020(7) 0.0037(6) -0.0011(7) C10 0.0280(8) 0.0233(8) 0.0246(8) -0.0016(7) 0.0031(7) 0.0042(7) C11 0.0352(9) 0.0216(8) 0.0225(8) -0.0002(7) 0.0024(7) 0.0030(8) O12 0.0326(6) 0.0225(6) 0.0273(6) 0.0014(5) -0.0035(5) -0.0015(5) C13 0.0270(8) 0.0292(9) 0.0239(8) -0.0068(7) 0.0094(7) -0.0039(8) C14 0.0276(8) 0.0378(10) 0.0236(8) -0.0020(8) 0.0085(7) -0.0019(8) C15 0.0299(9) 0.0612(14) 0.0306(9) -0.0048(10) 0.0032(8) -0.0036(10) C16 0.0342(10) 0.0565(14) 0.0485(12) -0.0236(11) 0.0092(9) -0.0127(10) C17 0.0380(10) 0.0343(10) 0.0588(12) -0.0193(10) 0.0202(10) -0.0083(9) C18 0.0303(9) 0.0263(9) 0.0430(10) -0.0064(8) 0.0109(8) -0.0004(8) C19 0.0287(9) 0.0451(12) 0.0289(9) 0.0078(9) 0.0028(7) 0.0013(9) N20 0.0480(10) 0.0447(11) 0.0575(11) 0.0182(9) 0.0016(9) 0.0019(9) C21 0.0282(8) 0.0210(8) 0.0253(8) -0.0066(7) 0.0064(7) 0.0022(7) C22 0.0337(9) 0.0332(9) 0.0301(9) -0.0032(8) 0.0092(8) 0.0050(8) C23 0.0459(11) 0.0544(12) 0.0360(10) 0.0032(10) 0.0186(9) 0.0001(10) C24 0.0329(10) 0.0772(16) 0.0475(12) -0.0079(12) 0.0207(9) -0.0023(11) C25 0.0283(9) 0.0695(15) 0.0457(11) -0.0052(11) 0.0040(9) 0.0088(10) C26 0.0333(9) 0.0425(11) 0.0317(9) -0.0024(9) 0.0045(8) 0.0040(9) 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' 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 C5 N1 C2 112.35(12) . . ? C5 N1 C9 113.28(12) . . ? C2 N1 C9 111.81(11) . . ? C5 N1 B8 103.61(11) . . ? C2 N1 B8 101.62(11) . . ? C9 N1 B8 113.34(11) . . ? N1 C2 C3 106.04(13) . . ? O3 C3 O4 123.93(15) . . ? O3 C3 C2 125.19(16) . . ? O4 C3 C2 110.88(13) . . ? C3 O4 B8 113.31(12) . . ? N1 C5 C6 105.31(12) . . ? O6 C6 O7 124.21(16) . . ? O6 C6 C5 124.95(16) . . ? O7 C6 C5 110.82(13) . . ? C6 O7 B8 114.22(12) . . ? O4 B8 O7 111.31(13) . . ? O4 B8 C21 113.85(13) . . ? O7 B8 C21 112.02(13) . . ? O4 B8 N1 102.13(12) . . ? O7 B8 N1 99.32(12) . . ? C21 B8 N1 117.01(13) . . ? N1 C9 C10 113.98(12) . . ? C11 C10 C9 111.44(13) . . ? O12 C11 C10 106.40(12) . . ? C13 O12 C11 118.78(12) . . ? O12 C13 C18 125.14(15) . . ? O12 C13 C14 115.40(14) . . ? C18 C13 C14 119.46(15) . . ? C15 C14 C13 120.32(16) . . ? C15 C14 C19 120.40(16) . . ? C13 C14 C19 119.28(14) . . ? C16 C15 C14 120.00(17) . . ? C17 C16 C15 119.62(17) . . ? C16 C17 C18 121.44(18) . . ? C17 C18 C13 119.15(17) . . ? N20 C19 C14 178.1(2) . . ? C26 C21 C22 116.91(16) . . ? C26 C21 B8 122.58(15) . . ? C22 C21 B8 120.49(14) . . ? C23 C22 C21 121.91(17) . . ? C24 C23 C22 119.79(18) . . ? C25 C24 C23 119.73(18) . . ? C24 C25 C26 120.50(18) . . ? C25 C26 C21 121.14(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 C5 1.4899(18) . ? N1 C2 1.4964(19) . ? N1 C9 1.5001(19) . ? N1 B8 1.662(2) . ? C2 C3 1.506(2) . ? C3 O3 1.2027(19) . ? C3 O4 1.334(2) . ? O4 B8 1.462(2) . ? C5 C6 1.513(2) . ? C6 O6 1.2025(18) . ? C6 O7 1.3272(19) . ? O7 B8 1.486(2) . ? B8 C21 1.581(2) . ? C9 C10 1.520(2) . ? C10 C11 1.508(2) . ? C11 O12 1.4361(18) . ? O12 C13 1.3564(18) . ? C13 C18 1.390(2) . ? C13 C14 1.398(2) . ? C14 C15 1.388(2) . ? C14 C19 1.441(3) . ? C15 C16 1.380(3) . ? C16 C17 1.376(3) . ? C17 C18 1.389(2) . ? C19 N20 1.142(2) . ? C21 C26 1.392(2) . ? C21 C22 1.394(2) . ? C22 C23 1.383(2) . ? C23 C24 1.374(3) . ? C24 C25 1.370(3) . ? C25 C26 1.388(3) . ?