#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:12:48 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247627 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/25/1552504.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_1552504 loop_ _publ_author_name 'Su, Xiaojun' 'Baker, J. J.' 'Martin, Caleb D.' _publ_section_title ; Dimeric boroles: effective sources of monomeric boroles for heterocycle synthesis ; _journal_issue 1 _journal_name_full 'Chemical Science' _journal_page_first 126 _journal_paper_doi 10.1039/C9SC04053F _journal_volume 11 _journal_year 2020 _chemical_absolute_configuration unk _chemical_formula_moiety 'C20 H22 B N' _chemical_formula_sum 'C20 H22 B N' _chemical_formula_weight 287.19 _chemical_properties_physical Air-sensitive,Moisture-sensitive _space_group_crystal_system orthorhombic _space_group_IT_number 43 _space_group_name_Hall 'F 2 -2d' _space_group_name_H-M_alt 'F d d 2' _symmetry_space_group_name_Hall 'F 2 -2d' _symmetry_space_group_name_H-M 'F d d 2' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_method SHELXL-2013 _audit_update_record ; 2019-07-24 deposited with the CCDC. 2019-10-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 32 _cell_length_a 39.763(2) _cell_length_b 37.788(2) _cell_length_c 8.9491(5) _cell_measurement_reflns_used 9884 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.07 _cell_measurement_theta_min 2.32 _cell_volume 13446.6(12) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014 (Sheldrick 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_unetI/netI 0.0278 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_k_max 46 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 70199 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.021 _diffrn_reflns_theta_min 2.156 _exptl_absorpt_coefficient_mu 0.064 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.909 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABs _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.135 _exptl_crystal_description block _exptl_crystal_F_000 4928 _exptl_crystal_size_max 0.269 _exptl_crystal_size_mid 0.227 _exptl_crystal_size_min 0.149 _refine_diff_density_max 0.223 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.049 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 406 _refine_ls_number_reflns 6608 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0618 _refine_ls_R_factor_gt 0.0468 _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^)+(0.0880P)^2^+4.9819P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1267 _refine_ls_wR_factor_ref 0.1391 _reflns_Friedel_coverage 0.873 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 1.000 _reflns_number_gt 5549 _reflns_number_total 6608 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc04053f2.cif _cod_data_source_block 1 _cod_depositor_comments ; The following automatic conversions were performed: '_atom_sites_solution_primary' value 'direct methods' was changed to 'direct'. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas Adding full bibliography for 1552504--1552508.cif. ; _cod_database_code 1552504 _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. ; _shelxl_version_number 2013-4 _shelx_res_file ; TITL 1 in Fdd2 New:Fdd2 CELL 0.71073 39.7630 37.7880 8.9491 90.000 90.000 90.000 ZERR 32 0.0020 0.0020 0.0005 0.000 0.000 0.000 LATT -4 SYMM - X , - Y , Z SYMM 0.25000 - X , 0.25000 + Y , 0.25000 + Z SYMM 0.75000 + X , 0.75000 - Y , 0.25000 + Z SFAC C H B N UNIT 640 704 32 32 L.S. 5 ACTA BOND $H FMAP 2 PLAN -20 CONF TWIN WGHT 0.088000 4.981900 BASF 1.36148 FVAR 0.01789 RESI 0 TEMP -123 N1 4 0.340811 0.179985 0.210720 11.00000 0.02652 0.03249 = 0.02807 0.00126 0.00108 0.00110 C4 1 0.384243 0.198686 0.398454 11.00000 0.03635 0.02968 = 0.03537 0.00180 -0.00265 -0.00230 C3 1 0.407647 0.197296 0.285193 11.00000 0.03155 0.02795 = 0.04068 0.00684 -0.00082 -0.00038 C2 1 0.398079 0.187672 0.135232 11.00000 0.03049 0.03295 = 0.03771 0.00602 0.00588 0.00057 C1 1 0.365426 0.179879 0.099108 11.00000 0.03480 0.03308 = 0.02851 0.00229 0.00649 -0.00128 C5 1 0.394417 0.210487 0.553645 11.00000 0.04881 0.06849 = 0.03906 -0.00398 -0.00661 -0.01083 AFIX 137 H5A 2 0.413527 0.196269 0.587973 11.00000 -1.50000 H5B 2 0.375449 0.207319 0.622274 11.00000 -1.50000 H5C 2 0.400862 0.235511 0.551161 11.00000 -1.50000 AFIX 0 C6 1 0.444309 0.205494 0.314840 11.00000 0.03404 0.05333 = 0.05898 0.00449 -0.00236 -0.00595 AFIX 137 H6A 2 0.447288 0.211556 0.420488 11.00000 -1.50000 H6B 2 0.451347 0.225508 0.252610 11.00000 -1.50000 H6C 2 0.458027 0.184726 0.290614 11.00000 -1.50000 AFIX 0 C7 1 0.424726 0.187200 0.014359 11.00000 0.03939 0.06788 = 0.05102 0.00006 0.01657 -0.00892 AFIX 137 H7A 2 0.415340 0.176795 -0.076868 11.00000 -1.50000 H7B 2 0.443949 0.173048 0.047909 11.00000 -1.50000 H7C 2 0.432134 0.211451 -0.006188 11.00000 -1.50000 AFIX 0 C8 1 0.354590 0.171780 -0.058153 11.00000 0.04600 0.06310 = 0.02946 -0.00303 0.00583 -0.00119 AFIX 137 H8A 2 0.365796 0.188061 -0.127340 11.00000 -1.50000 H8B 2 0.330165 0.174627 -0.066533 11.00000 -1.50000 H8C 2 0.360744 0.147373 -0.083104 11.00000 -1.50000 AFIX 0 C9 1 0.319977 0.184521 0.487024 11.00000 0.02940 0.04068 = 0.02639 -0.00538 -0.00236 0.00150 C10 1 0.307450 0.151648 0.527713 11.00000 0.03493 0.04138 = 0.04142 0.00420 0.00595 0.00515 AFIX 43 H10 2 0.315622 0.131116 0.478374 11.00000 -1.20000 AFIX 0 C11 1 0.283242 0.147937 0.638831 11.00000 0.03710 0.06134 = 0.05062 0.01741 0.00721 0.00259 AFIX 43 H11 2 0.275170 0.125083 0.664718 11.00000 -1.20000 AFIX 0 C12 1 0.271073 0.177134 0.710730 11.00000 0.03453 0.08732 = 0.02855 -0.00044 0.00237 -0.00176 AFIX 43 H12 2 0.254252 0.174622 0.785367 11.00000 -1.20000 AFIX 0 C13 1 0.282973 0.209635 0.675663 11.00000 0.04732 0.06352 = 0.04888 -0.02177 0.00796 0.00455 AFIX 43 H13 2 0.274502 0.229917 0.725843 11.00000 -1.20000 AFIX 0 C14 1 0.307521 0.213425 0.566593 11.00000 0.05555 0.04398 = 0.04824 -0.00858 0.00994 -0.00559 AFIX 43 H14 2 0.316084 0.236359 0.545529 11.00000 -1.20000 AFIX 0 C15 1 0.306047 0.173165 0.168058 11.00000 0.02965 0.04231 = 0.02171 -0.00048 0.00394 0.00188 C16 1 0.284893 0.201664 0.143426 11.00000 0.04026 0.04617 = 0.04510 0.00204 0.00092 0.00714 AFIX 43 H16 2 0.293165 0.225136 0.153169 11.00000 -1.20000 AFIX 0 C17 1 0.251886 0.195907 0.104831 11.00000 0.04021 0.07631 = 0.04567 0.00146 -0.00064 0.01926 AFIX 43 H17 2 0.237443 0.215501 0.087333 11.00000 -1.20000 AFIX 0 C18 1 0.239585 0.162084 0.091320 11.00000 0.03070 0.10198 = 0.02991 0.00108 -0.00224 -0.00120 AFIX 43 H18 2 0.216669 0.158187 0.066206 11.00000 -1.20000 AFIX 0 C19 1 0.260858 0.133972 0.114603 11.00000 0.04745 0.06864 = 0.05703 -0.00071 -0.01039 -0.01718 AFIX 43 H19 2 0.252523 0.110537 0.104332 11.00000 -1.20000 AFIX 0 C20 1 0.294378 0.139225 0.152944 11.00000 0.04120 0.04475 = 0.04617 -0.00215 -0.00664 -0.00481 AFIX 43 H20 2 0.308936 0.119630 0.168393 11.00000 -1.20000 AFIX 0 B1 3 0.348324 0.188145 0.364681 11.00000 0.03258 0.02638 = 0.02935 -0.00141 0.00137 0.00069 N2 4 0.353510 0.064089 0.570607 11.00000 0.02650 0.03774 = 0.02271 0.00221 0.00347 -0.00027 C21 1 0.308129 0.048899 0.387364 11.00000 0.03471 0.02629 = 0.02627 0.00119 -0.00001 -0.00129 C22 1 0.285806 0.049192 0.504418 11.00000 0.03205 0.02854 = 0.03207 0.00120 -0.00002 -0.00198 C23 1 0.297091 0.054650 0.654768 11.00000 0.03216 0.03809 = 0.02669 -0.00043 0.00724 -0.00307 C24 1 0.330035 0.062072 0.686697 11.00000 0.03296 0.03939 = 0.02262 -0.00060 0.00282 0.00328 C25 1 0.296383 0.040731 0.229322 11.00000 0.04054 0.05099 = 0.02891 0.00018 -0.00430 -0.01051 AFIX 137 H25A 2 0.315671 0.041337 0.161201 11.00000 -1.50000 H25B 2 0.279796 0.058431 0.198092 11.00000 -1.50000 H25C 2 0.286112 0.017163 0.226852 11.00000 -1.50000 AFIX 0 C26 1 0.248514 0.043735 0.479544 11.00000 0.03259 0.06007 = 0.04251 -0.00002 -0.00063 -0.00657 AFIX 137 H26A 2 0.243142 0.047886 0.374116 11.00000 -1.50000 H26B 2 0.235825 0.060356 0.541893 11.00000 -1.50000 H26C 2 0.242429 0.019429 0.506517 11.00000 -1.50000 AFIX 0 C27 1 0.272221 0.051435 0.783129 11.00000 0.03957 0.05949 = 0.03734 -0.00270 0.01099 -0.00962 AFIX 137 H27A 2 0.260312 0.073936 0.795946 11.00000 -1.50000 H27B 2 0.284351 0.045637 0.875259 11.00000 -1.50000 H27C 2 0.255972 0.032659 0.760910 11.00000 -1.50000 AFIX 0 C28 1 0.342161 0.068350 0.843813 11.00000 0.03951 0.07656 = 0.02351 -0.00355 0.00095 -0.00401 AFIX 137 H28A 2 0.344089 0.045656 0.896121 11.00000 -1.50000 H28B 2 0.326092 0.083536 0.896558 11.00000 -1.50000 H28C 2 0.364198 0.079944 0.841053 11.00000 -1.50000 AFIX 0 C29 1 0.372928 0.057195 0.293916 11.00000 0.03019 0.03336 = 0.02136 0.00102 -0.00111 -0.00105 C30 1 0.385343 0.088284 0.229971 11.00000 0.03378 0.03533 = 0.03360 0.00367 -0.00134 -0.00234 AFIX 43 H30 2 0.377249 0.110511 0.264130 11.00000 -1.20000 AFIX 0 C31 1 0.409289 0.087221 0.117453 11.00000 0.03387 0.05946 = 0.03653 0.01398 0.00035 -0.01051 AFIX 43 H31 2 0.416978 0.108664 0.073820 11.00000 -1.20000 AFIX 0 C32 1 0.422012 0.055480 0.068407 11.00000 0.03443 0.08151 = 0.02825 -0.00403 0.00636 -0.00475 AFIX 43 H32 2 0.438800 0.054934 -0.007090 11.00000 -1.20000 AFIX 0 C33 1 0.410233 0.024577 0.129541 11.00000 0.05911 0.05586 = 0.05065 -0.01812 0.01727 0.00354 AFIX 43 H33 2 0.418809 0.002517 0.095773 11.00000 -1.20000 AFIX 0 C34 1 0.385868 0.025379 0.240390 11.00000 0.05559 0.03546 = 0.05069 -0.00446 0.01775 -0.00107 AFIX 43 H34 2 0.377818 0.003723 0.280742 11.00000 -1.20000 AFIX 0 C35 1 0.388039 0.073309 0.606759 11.00000 0.02837 0.05168 = 0.02097 0.00115 0.00039 -0.00098 C36 1 0.396853 0.108534 0.621955 11.00000 0.04180 0.05749 = 0.04222 -0.01389 -0.00379 -0.00660 AFIX 43 H36 2 0.380546 0.126648 0.608941 11.00000 -1.20000 AFIX 0 C37 1 0.429947 0.116980 0.656565 11.00000 0.05151 0.08775 = 0.05165 -0.01467 -0.00389 -0.02319 AFIX 43 H37 2 0.436271 0.141064 0.668275 11.00000 -1.20000 AFIX 0 C38 1 0.453684 0.090746 0.674064 11.00000 0.03212 0.12345 = 0.03388 0.00769 -0.00287 -0.01940 AFIX 43 H38 2 0.476215 0.096770 0.698558 11.00000 -1.20000 AFIX 0 C39 1 0.444787 0.055902 0.656114 11.00000 0.03040 0.10152 = 0.04731 0.02666 0.00373 0.00385 AFIX 43 H39 2 0.461258 0.037854 0.666356 11.00000 -1.20000 AFIX 0 C40 1 0.411808 0.047038 0.623078 11.00000 0.03369 0.06646 = 0.03985 0.01554 0.00366 0.00297 AFIX 43 H40 2 0.405590 0.022914 0.611698 11.00000 -1.20000 AFIX 0 B2 3 0.344628 0.056778 0.417317 11.00000 0.03206 0.02286 = 0.02198 0.00302 0.00213 0.00056 HKLF 4 1 0.0000 1.0000 0.0000 -1.0000 0.0000 0.0000 0.0000 0.0000 1.0000 REM 1 in Fdd2 New:Fdd2 REM R1 = 0.0468 for 5549 Fo > 4sig(Fo) and 0.0618 for all 6608 data REM 406 parameters refined using 1 restraints END WGHT 0.0880 4.9819 REM Highest difference peak 0.223, deepest hole -0.179, 1-sigma level 0.049 Q1 1 0.2951 0.2214 0.4843 11.00000 0.05 0.22 Q2 1 0.3654 0.0532 0.8630 11.00000 0.05 0.21 Q3 1 0.2706 0.2234 0.6026 11.00000 0.05 0.20 Q4 1 0.3817 0.1859 0.1157 11.00000 0.05 0.20 Q5 1 0.4499 0.1898 0.3798 11.00000 0.05 0.19 Q6 1 0.2663 0.1970 0.6809 11.00000 0.05 0.19 Q7 1 0.4440 0.2008 0.0318 11.00000 0.05 0.19 Q8 1 0.4097 0.1921 0.0750 11.00000 0.05 0.19 Q9 1 0.4490 0.2302 0.3703 11.00000 0.05 0.17 Q10 1 0.3753 0.2293 0.5985 11.00000 0.05 0.17 Q11 1 0.3877 0.1993 0.6009 11.00000 0.05 0.17 Q12 1 0.4244 0.0722 0.1181 11.00000 0.05 0.16 Q13 1 0.3383 0.1506 -0.0740 11.00000 0.05 0.16 Q14 1 0.4135 0.0410 0.1019 11.00000 0.05 0.15 Q15 1 0.4110 0.1996 -0.0950 11.00000 0.05 0.15 Q16 1 0.4628 0.2018 0.2035 11.00000 0.05 0.15 Q17 1 0.4509 0.0701 0.0186 11.00000 0.05 0.15 Q18 1 0.3177 0.0229 0.1730 11.00000 0.05 0.15 Q19 1 0.4198 0.0588 0.6738 11.00000 0.05 0.14 Q20 1 0.3689 0.1912 0.3854 11.00000 0.05 0.14 ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z' '-x+1/4, y+1/4, z+1/4' 'x+3/4, -y+3/4, z+1/4' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' '-x+1/4, y+3/4, z+3/4' 'x+3/4, -y+5/4, z+3/4' 'x+1/2, y, z+1/2' '-x+1/2, -y, z+1/2' '-x+3/4, y+1/4, z+3/4' 'x+5/4, -y+3/4, z+3/4' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z' '-x+3/4, y+3/4, z+1/4' 'x+5/4, -y+5/4, z+1/4' 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 N1 N 0.34081(6) 0.17998(6) 0.2107(3) 0.0290(5) Uani 1 1 d . . C4 C 0.38424(7) 0.19869(8) 0.3985(4) 0.0338(6) Uani 1 1 d . . C3 C 0.40765(7) 0.19730(7) 0.2852(4) 0.0334(7) Uani 1 1 d . . C2 C 0.39808(7) 0.18767(8) 0.1352(4) 0.0337(7) Uani 1 1 d . . C1 C 0.36543(7) 0.17988(7) 0.0991(3) 0.0321(7) Uani 1 1 d . . C5 C 0.39442(9) 0.21049(11) 0.5536(4) 0.0521(9) Uani 1 1 d . . H5A H 0.4135 0.1963 0.5880 0.078 Uiso 1 1 calc R U H5B H 0.3754 0.2073 0.6223 0.078 Uiso 1 1 calc R U H5C H 0.4009 0.2355 0.5512 0.078 Uiso 1 1 calc R U C6 C 0.44431(8) 0.20549(9) 0.3148(5) 0.0488(9) Uani 1 1 d . . H6A H 0.4473 0.2116 0.4205 0.073 Uiso 1 1 calc R U H6B H 0.4513 0.2255 0.2526 0.073 Uiso 1 1 calc R U H6C H 0.4580 0.1847 0.2906 0.073 Uiso 1 1 calc R U C7 C 0.42473(9) 0.18720(11) 0.0144(5) 0.0528(9) Uani 1 1 d . . H7A H 0.4153 0.1768 -0.0769 0.079 Uiso 1 1 calc R U H7B H 0.4439 0.1730 0.0479 0.079 Uiso 1 1 calc R U H7C H 0.4321 0.2115 -0.0062 0.079 Uiso 1 1 calc R U C8 C 0.35459(9) 0.17178(10) -0.0582(4) 0.0462(8) Uani 1 1 d . . H8A H 0.3658 0.1881 -0.1273 0.069 Uiso 1 1 calc R U H8B H 0.3302 0.1746 -0.0665 0.069 Uiso 1 1 calc R U H8C H 0.3607 0.1474 -0.0831 0.069 Uiso 1 1 calc R U C9 C 0.31998(7) 0.18452(8) 0.4870(3) 0.0322(6) Uani 1 1 d . . C10 C 0.30745(7) 0.15165(8) 0.5277(4) 0.0392(7) Uani 1 1 d . . H10 H 0.3156 0.1311 0.4784 0.047 Uiso 1 1 calc R U C11 C 0.28324(8) 0.14794(10) 0.6388(4) 0.0497(9) Uani 1 1 d . . H11 H 0.2752 0.1251 0.6647 0.060 Uiso 1 1 calc R U C12 C 0.27107(8) 0.17713(12) 0.7107(4) 0.0501(9) Uani 1 1 d . . H12 H 0.2543 0.1746 0.7854 0.060 Uiso 1 1 calc R U C13 C 0.28297(9) 0.20964(11) 0.6757(4) 0.0532(9) Uani 1 1 d . . H13 H 0.2745 0.2299 0.7258 0.064 Uiso 1 1 calc R U C14 C 0.30752(9) 0.21342(9) 0.5666(4) 0.0493(9) Uani 1 1 d . . H14 H 0.3161 0.2364 0.5455 0.059 Uiso 1 1 calc R U C15 C 0.30605(7) 0.17316(8) 0.1681(3) 0.0312(6) Uani 1 1 d . . C16 C 0.28489(8) 0.20166(9) 0.1434(4) 0.0438(8) Uani 1 1 d . . H16 H 0.2932 0.2251 0.1532 0.053 Uiso 1 1 calc R U C17 C 0.25189(9) 0.19591(11) 0.1048(4) 0.0541(10) Uani 1 1 d . . H17 H 0.2374 0.2155 0.0873 0.065 Uiso 1 1 calc R U C18 C 0.23959(8) 0.16208(12) 0.0913(4) 0.0542(10) Uani 1 1 d . . H18 H 0.2167 0.1582 0.0662 0.065 Uiso 1 1 calc R U C19 C 0.26086(9) 0.13397(11) 0.1146(5) 0.0577(10) Uani 1 1 d . . H19 H 0.2525 0.1105 0.1043 0.069 Uiso 1 1 calc R U C20 C 0.29438(8) 0.13923(9) 0.1529(4) 0.0440(8) Uani 1 1 d . . H20 H 0.3089 0.1196 0.1684 0.053 Uiso 1 1 calc R U B1 B 0.34832(8) 0.18814(8) 0.3647(4) 0.0294(7) Uani 1 1 d . . N2 N 0.35351(6) 0.06409(6) 0.5706(3) 0.0290(5) Uani 1 1 d . . C21 C 0.30813(7) 0.04890(7) 0.3874(3) 0.0291(6) Uani 1 1 d . . C22 C 0.28581(7) 0.04919(7) 0.5044(3) 0.0309(6) Uani 1 1 d . . C23 C 0.29709(7) 0.05465(8) 0.6548(3) 0.0323(6) Uani 1 1 d . . C24 C 0.33003(7) 0.06207(8) 0.6867(3) 0.0317(6) Uani 1 1 d . . C25 C 0.29638(8) 0.04073(9) 0.2293(3) 0.0402(7) Uani 1 1 d . . H25A H 0.3157 0.0413 0.1612 0.060 Uiso 1 1 calc R U H25B H 0.2798 0.0584 0.1981 0.060 Uiso 1 1 calc R U H25C H 0.2861 0.0172 0.2269 0.060 Uiso 1 1 calc R U C26 C 0.24851(8) 0.04373(10) 0.4795(4) 0.0451(8) Uani 1 1 d . . H26A H 0.2431 0.0479 0.3741 0.068 Uiso 1 1 calc R U H26B H 0.2358 0.0604 0.5419 0.068 Uiso 1 1 calc R U H26C H 0.2424 0.0194 0.5065 0.068 Uiso 1 1 calc R U C27 C 0.27222(8) 0.05143(10) 0.7831(4) 0.0455(8) Uani 1 1 d . . H27A H 0.2603 0.0739 0.7959 0.068 Uiso 1 1 calc R U H27B H 0.2844 0.0456 0.8753 0.068 Uiso 1 1 calc R U H27C H 0.2560 0.0327 0.7609 0.068 Uiso 1 1 calc R U C28 C 0.34216(9) 0.06835(11) 0.8438(4) 0.0465(8) Uani 1 1 d . . H28A H 0.3441 0.0457 0.8961 0.070 Uiso 1 1 calc R U H28B H 0.3261 0.0835 0.8966 0.070 Uiso 1 1 calc R U H28C H 0.3642 0.0799 0.8411 0.070 Uiso 1 1 calc R U C29 C 0.37293(7) 0.05720(7) 0.2939(3) 0.0283(6) Uani 1 1 d . . C30 C 0.38534(7) 0.08828(8) 0.2300(4) 0.0342(6) Uani 1 1 d . . H30 H 0.3772 0.1105 0.2641 0.041 Uiso 1 1 calc R U C31 C 0.40929(8) 0.08722(10) 0.1175(4) 0.0433(8) Uani 1 1 d . . H31 H 0.4170 0.1087 0.0738 0.052 Uiso 1 1 calc R U C32 C 0.42201(8) 0.05548(11) 0.0684(4) 0.0481(9) Uani 1 1 d . . H32 H 0.4388 0.0549 -0.0071 0.058 Uiso 1 1 calc R U C33 C 0.41023(9) 0.02458(10) 0.1295(4) 0.0552(10) Uani 1 1 d . . H33 H 0.4188 0.0025 0.0958 0.066 Uiso 1 1 calc R U C34 C 0.38587(9) 0.02538(9) 0.2404(4) 0.0472(8) Uani 1 1 d . . H34 H 0.3778 0.0037 0.2807 0.057 Uiso 1 1 calc R U C35 C 0.38804(7) 0.07331(8) 0.6068(3) 0.0337(7) Uani 1 1 d . . C36 C 0.39685(8) 0.10853(10) 0.6220(4) 0.0472(8) Uani 1 1 d . . H36 H 0.3805 0.1266 0.6089 0.057 Uiso 1 1 calc R U C37 C 0.42995(10) 0.11698(12) 0.6566(5) 0.0636(11) Uani 1 1 d . . H37 H 0.4363 0.1411 0.6683 0.076 Uiso 1 1 calc R U C38 C 0.45368(9) 0.09075(14) 0.6741(4) 0.0632(12) Uani 1 1 d . . H38 H 0.4762 0.0968 0.6986 0.076 Uiso 1 1 calc R U C39 C 0.44479(9) 0.05590(13) 0.6561(5) 0.0597(11) Uani 1 1 d . . H39 H 0.4613 0.0379 0.6664 0.072 Uiso 1 1 calc R U C40 C 0.41181(8) 0.04704(10) 0.6231(4) 0.0467(9) Uani 1 1 d . . H40 H 0.4056 0.0229 0.6117 0.056 Uiso 1 1 calc R U B2 B 0.34463(8) 0.05678(8) 0.4173(3) 0.0256(7) Uani 1 1 d . . 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 0.0265(12) 0.0325(12) 0.0281(12) 0.0013(10) 0.0011(10) 0.0011(10) C4 0.0363(16) 0.0297(14) 0.0354(16) 0.0018(13) -0.0027(13) -0.0023(12) C3 0.0316(15) 0.0279(14) 0.0407(17) 0.0068(12) -0.0008(13) -0.0004(11) C2 0.0305(15) 0.0330(14) 0.0377(17) 0.0060(12) 0.0059(13) 0.0006(12) C1 0.0348(16) 0.0331(14) 0.0285(15) 0.0023(12) 0.0065(13) -0.0013(12) C5 0.049(2) 0.068(2) 0.039(2) -0.0040(17) -0.0066(16) -0.0108(17) C6 0.0340(17) 0.053(2) 0.059(2) 0.0045(18) -0.0024(16) -0.0060(14) C7 0.0394(18) 0.068(2) 0.051(2) 0.0001(18) 0.0166(17) -0.0089(16) C8 0.0460(19) 0.063(2) 0.0295(17) -0.0030(15) 0.0058(14) -0.0012(16) C9 0.0294(15) 0.0407(16) 0.0264(15) -0.0054(13) -0.0024(12) 0.0015(12) C10 0.0349(16) 0.0414(16) 0.0414(18) 0.0042(14) 0.0059(14) 0.0052(13) C11 0.0371(17) 0.061(2) 0.051(2) 0.0174(18) 0.0072(16) 0.0026(15) C12 0.0345(18) 0.087(3) 0.0286(16) -0.0004(17) 0.0024(14) -0.0018(18) C13 0.0473(19) 0.064(2) 0.049(2) -0.0218(18) 0.0080(17) 0.0046(17) C14 0.056(2) 0.0440(18) 0.048(2) -0.0086(16) 0.0099(17) -0.0056(15) C15 0.0297(14) 0.0423(16) 0.0217(14) -0.0005(12) 0.0039(12) 0.0019(12) C16 0.0403(18) 0.0462(18) 0.0451(19) 0.0020(16) 0.0009(15) 0.0071(14) C17 0.0402(18) 0.076(3) 0.046(2) 0.0015(19) -0.0006(16) 0.0193(18) C18 0.0307(16) 0.102(3) 0.0299(17) 0.0011(18) -0.0022(14) -0.0012(19) C19 0.047(2) 0.069(2) 0.057(2) -0.0007(19) -0.0104(18) -0.0172(18) C20 0.0412(18) 0.0448(18) 0.046(2) -0.0021(15) -0.0066(16) -0.0048(14) B1 0.0326(17) 0.0264(15) 0.0293(17) -0.0014(12) 0.0014(14) 0.0007(12) N2 0.0265(12) 0.0377(13) 0.0227(11) 0.0022(10) 0.0035(10) -0.0003(10) C21 0.0347(15) 0.0263(13) 0.0263(14) 0.0012(11) 0.0000(12) -0.0013(11) C22 0.0321(15) 0.0285(14) 0.0321(15) 0.0012(12) 0.0000(13) -0.0020(11) C23 0.0322(15) 0.0381(15) 0.0267(15) -0.0004(12) 0.0072(12) -0.0031(12) C24 0.0330(16) 0.0394(16) 0.0226(14) -0.0006(12) 0.0028(12) 0.0033(12) C25 0.0405(17) 0.0510(18) 0.0289(16) 0.0002(14) -0.0043(14) -0.0105(14) C26 0.0326(16) 0.060(2) 0.0425(19) 0.0000(16) -0.0006(14) -0.0066(15) C27 0.0396(18) 0.059(2) 0.0373(18) -0.0027(16) 0.0110(15) -0.0096(15) C28 0.0395(18) 0.077(2) 0.0235(16) -0.0035(16) 0.0010(14) -0.0040(16) C29 0.0302(14) 0.0334(15) 0.0214(14) 0.0010(11) -0.0011(11) -0.0011(11) C30 0.0338(15) 0.0353(15) 0.0336(16) 0.0037(13) -0.0013(13) -0.0023(12) C31 0.0339(16) 0.059(2) 0.0365(17) 0.0140(16) 0.0004(14) -0.0105(15) C32 0.0344(17) 0.082(3) 0.0283(16) -0.0040(17) 0.0064(14) -0.0048(17) C33 0.059(2) 0.056(2) 0.051(2) -0.0181(18) 0.0173(18) 0.0035(17) C34 0.056(2) 0.0355(16) 0.051(2) -0.0045(15) 0.0177(17) -0.0011(15) C35 0.0284(14) 0.0517(18) 0.0210(14) 0.0011(13) 0.0004(11) -0.0010(13) C36 0.0418(18) 0.057(2) 0.0422(19) -0.0139(16) -0.0038(15) -0.0066(15) C37 0.052(2) 0.088(3) 0.052(2) -0.015(2) -0.0039(19) -0.023(2) C38 0.0321(19) 0.123(4) 0.0339(19) 0.008(2) -0.0029(15) -0.019(2) C39 0.0304(17) 0.102(3) 0.047(2) 0.027(2) 0.0037(16) 0.0038(19) C40 0.0337(17) 0.066(2) 0.040(2) 0.0155(16) 0.0037(14) 0.0030(15) B2 0.0321(17) 0.0229(14) 0.0220(15) 0.0030(12) 0.0021(13) 0.0006(12) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 B1 122.5(2) C1 N1 C15 118.4(2) B1 N1 C15 119.0(2) C3 C4 B1 118.7(3) C3 C4 C5 120.4(3) B1 C4 C5 120.9(3) C4 C3 C2 121.1(3) C4 C3 C6 120.9(3) C2 C3 C6 118.0(3) C1 C2 C3 121.6(3) C1 C2 C7 119.5(3) C3 C2 C7 118.9(3) C2 C1 N1 119.6(3) C2 C1 C8 122.4(3) N1 C1 C8 117.9(3) C4 C5 H5A 109.5 C4 C5 H5B 109.5 H5A C5 H5B 109.5 C4 C5 H5C 109.5 H5A C5 H5C 109.5 H5B C5 H5C 109.5 C3 C6 H6A 109.5 C3 C6 H6B 109.5 H6A C6 H6B 109.5 C3 C6 H6C 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 C2 C7 H7A 109.5 C2 C7 H7B 109.5 H7A C7 H7B 109.5 C2 C7 H7C 109.5 H7A C7 H7C 109.5 H7B C7 H7C 109.5 C1 C8 H8A 109.5 C1 C8 H8B 109.5 H8A C8 H8B 109.5 C1 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C10 C9 C14 116.1(3) C10 C9 B1 121.1(3) C14 C9 B1 122.7(3) C9 C10 C11 121.8(3) C9 C10 H10 119.1 C11 C10 H10 119.1 C12 C11 C10 120.0(3) C12 C11 H11 120.0 C10 C11 H11 120.0 C13 C12 C11 120.0(3) C13 C12 H12 120.0 C11 C12 H12 120.0 C12 C13 C14 120.2(3) C12 C13 H13 119.9 C14 C13 H13 119.9 C13 C14 C9 121.9(3) C13 C14 H14 119.1 C9 C14 H14 119.1 C20 C15 C16 120.4(3) C20 C15 N1 120.8(3) C16 C15 N1 118.7(3) C17 C16 C15 119.8(3) C17 C16 H16 120.1 C15 C16 H16 120.1 C18 C17 C16 120.6(3) C18 C17 H17 119.7 C16 C17 H17 119.7 C19 C18 C17 119.1(3) C19 C18 H18 120.4 C17 C18 H18 120.4 C18 C19 C20 121.1(4) C18 C19 H19 119.4 C20 C19 H19 119.4 C15 C20 C19 118.8(3) C15 C20 H20 120.6 C19 C20 H20 120.6 N1 B1 C4 116.3(3) N1 B1 C9 119.8(3) C4 B1 C9 124.0(3) C24 N2 B2 122.2(2) C24 N2 C35 118.6(2) B2 N2 C35 119.3(2) C22 C21 B2 119.1(3) C22 C21 C25 120.8(3) B2 C21 C25 120.1(3) C21 C22 C23 121.0(3) C21 C22 C26 121.3(3) C23 C22 C26 117.7(3) C24 C23 C22 121.6(3) C24 C23 C27 118.7(3) C22 C23 C27 119.6(3) C23 C24 N2 119.6(3) C23 C24 C28 122.2(3) N2 C24 C28 118.1(3) C21 C25 H25A 109.5 C21 C25 H25B 109.5 H25A C25 H25B 109.5 C21 C25 H25C 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 C22 C26 H26A 109.5 C22 C26 H26B 109.5 H26A C26 H26B 109.5 C22 C26 H26C 109.5 H26A C26 H26C 109.5 H26B C26 H26C 109.5 C23 C27 H27A 109.5 C23 C27 H27B 109.5 H27A C27 H27B 109.5 C23 C27 H27C 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 C24 C28 H28A 109.5 C24 C28 H28B 109.5 H28A C28 H28B 109.5 C24 C28 H28C 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 C34 C29 C30 117.0(3) C34 C29 B2 119.7(3) C30 C29 B2 123.2(3) C31 C30 C29 121.1(3) C31 C30 H30 119.5 C29 C30 H30 119.5 C32 C31 C30 120.7(3) C32 C31 H31 119.7 C30 C31 H31 119.7 C33 C32 C31 119.3(3) C33 C32 H32 120.3 C31 C32 H32 120.3 C32 C33 C34 120.3(3) C32 C33 H33 119.8 C34 C33 H33 119.8 C33 C34 C29 121.5(3) C33 C34 H34 119.2 C29 C34 H34 119.2 C40 C35 C36 120.6(3) C40 C35 N2 119.9(3) C36 C35 N2 119.5(3) C35 C36 C37 118.9(4) C35 C36 H36 120.6 C37 C36 H36 120.6 C38 C37 C36 120.6(4) C38 C37 H37 119.7 C36 C37 H37 119.7 C39 C38 C37 120.0(3) C39 C38 H38 120.0 C37 C38 H38 120.0 C38 C39 C40 120.1(4) C38 C39 H39 120.0 C40 C39 H39 120.0 C35 C40 C39 119.8(4) C35 C40 H40 120.1 C39 C40 H40 120.1 N2 B2 C21 116.3(3) N2 B2 C29 119.3(3) C21 B2 C29 124.4(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C1 1.398(4) N1 B1 1.443(4) N1 C15 1.457(4) C4 C3 1.377(4) C4 B1 1.513(4) C4 C5 1.514(5) C3 C2 1.442(5) C3 C6 1.514(4) C2 C1 1.370(4) C2 C7 1.514(4) C1 C8 1.503(5) C5 H5A 0.9800 C5 H5B 0.9800 C5 H5C 0.9800 C6 H6A 0.9800 C6 H6B 0.9800 C6 H6C 0.9800 C7 H7A 0.9800 C7 H7B 0.9800 C7 H7C 0.9800 C8 H8A 0.9800 C8 H8B 0.9800 C8 H8C 0.9800 C9 C10 1.387(4) C9 C14 1.395(4) C9 B1 1.577(4) C10 C11 1.391(5) C10 H10 0.9500 C11 C12 1.366(5) C11 H11 0.9500 C12 C13 1.353(6) C12 H12 0.9500 C13 C14 1.388(5) C13 H13 0.9500 C14 H14 0.9500 C15 C20 1.371(4) C15 C16 1.384(4) C16 C17 1.374(5) C16 H16 0.9500 C17 C18 1.374(6) C17 H17 0.9500 C18 C19 1.374(6) C18 H18 0.9500 C19 C20 1.391(5) C19 H19 0.9500 C20 H20 0.9500 N2 C24 1.399(4) N2 B2 1.443(4) N2 C35 1.453(4) C21 C22 1.373(4) C21 B2 1.506(4) C21 C25 1.521(4) C22 C23 1.433(4) C22 C26 1.514(4) C23 C24 1.370(4) C23 C27 1.521(4) C24 C28 1.505(4) C25 H25A 0.9800 C25 H25B 0.9800 C25 H25C 0.9800 C26 H26A 0.9800 C26 H26B 0.9800 C26 H26C 0.9800 C27 H27A 0.9800 C27 H27B 0.9800 C27 H27C 0.9800 C28 H28A 0.9800 C28 H28B 0.9800 C28 H28C 0.9800 C29 C34 1.393(4) C29 C30 1.397(4) C29 B2 1.577(4) C30 C31 1.386(4) C30 H30 0.9500 C31 C32 1.374(5) C31 H31 0.9500 C32 C33 1.372(5) C32 H32 0.9500 C33 C34 1.387(5) C33 H33 0.9500 C34 H34 0.9500 C35 C40 1.378(5) C35 C36 1.383(5) C36 C37 1.389(5) C36 H36 0.9500 C37 C38 1.378(6) C37 H37 0.9500 C38 C39 1.373(7) C38 H38 0.9500 C39 C40 1.385(5) C39 H39 0.9500 C40 H40 0.9500 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 B1 C4 C3 C2 3.0(4) C5 C4 C3 C2 -177.1(3) B1 C4 C3 C6 -176.4(3) C5 C4 C3 C6 3.5(5) C4 C3 C2 C1 0.6(4) C6 C3 C2 C1 -180.0(3) C4 C3 C2 C7 178.9(3) C6 C3 C2 C7 -1.7(4) C3 C2 C1 N1 -2.3(4) C7 C2 C1 N1 179.4(3) C3 C2 C1 C8 176.5(3) C7 C2 C1 C8 -1.8(5) B1 N1 C1 C2 0.2(4) C15 N1 C1 C2 177.3(3) B1 N1 C1 C8 -178.7(3) C15 N1 C1 C8 -1.5(4) C14 C9 C10 C11 1.6(5) B1 C9 C10 C11 177.9(3) C9 C10 C11 C12 0.2(5) C10 C11 C12 C13 -1.1(5) C11 C12 C13 C14 0.1(6) C12 C13 C14 C9 1.9(6) C10 C9 C14 C13 -2.7(5) B1 C9 C14 C13 -178.9(3) C1 N1 C15 C20 83.9(4) B1 N1 C15 C20 -98.9(3) C1 N1 C15 C16 -96.3(3) B1 N1 C15 C16 80.9(3) C20 C15 C16 C17 0.6(5) N1 C15 C16 C17 -179.2(3) C15 C16 C17 C18 0.4(5) C16 C17 C18 C19 -1.0(6) C17 C18 C19 C20 0.7(6) C16 C15 C20 C19 -0.9(5) N1 C15 C20 C19 178.9(3) C18 C19 C20 C15 0.3(6) C1 N1 B1 C4 3.3(4) C15 N1 B1 C4 -173.8(2) C1 N1 B1 C9 -174.7(2) C15 N1 B1 C9 8.2(4) C3 C4 B1 N1 -4.8(4) C5 C4 B1 N1 175.3(3) C3 C4 B1 C9 173.1(3) C5 C4 B1 C9 -6.8(5) C10 C9 B1 N1 68.6(4) C14 C9 B1 N1 -115.4(3) C10 C9 B1 C4 -109.2(3) C14 C9 B1 C4 66.8(4) B2 C21 C22 C23 -4.0(4) C25 C21 C22 C23 176.0(3) B2 C21 C22 C26 176.1(3) C25 C21 C22 C26 -3.9(4) C21 C22 C23 C24 4.4(4) C26 C22 C23 C24 -175.7(3) C21 C22 C23 C27 -174.4(3) C26 C22 C23 C27 5.6(4) C22 C23 C24 N2 -0.6(4) C27 C23 C24 N2 178.1(3) C22 C23 C24 C28 179.2(3) C27 C23 C24 C28 -2.1(4) B2 N2 C24 C23 -3.3(4) C35 N2 C24 C23 177.7(3) B2 N2 C24 C28 176.9(3) C35 N2 C24 C28 -2.1(4) C34 C29 C30 C31 0.5(4) B2 C29 C30 C31 -177.4(3) C29 C30 C31 C32 -1.6(5) C30 C31 C32 C33 1.5(5) C31 C32 C33 C34 -0.4(6) C32 C33 C34 C29 -0.7(6) C30 C29 C34 C33 0.6(5) B2 C29 C34 C33 178.5(3) C24 N2 C35 C40 97.6(3) B2 N2 C35 C40 -81.4(4) C24 N2 C35 C36 -83.5(3) B2 N2 C35 C36 97.5(3) C40 C35 C36 C37 -1.1(5) N2 C35 C36 C37 180.0(3) C35 C36 C37 C38 0.6(6) C36 C37 C38 C39 0.5(6) C37 C38 C39 C40 -1.2(6) C36 C35 C40 C39 0.5(5) N2 C35 C40 C39 179.4(3) C38 C39 C40 C35 0.7(6) C24 N2 B2 C21 3.5(4) C35 N2 B2 C21 -177.5(2) C24 N2 B2 C29 -176.1(2) C35 N2 B2 C29 2.9(4) C22 C21 B2 N2 0.2(4) C25 C21 B2 N2 -179.8(3) C22 C21 B2 C29 179.8(2) C25 C21 B2 C29 -0.2(4) C34 C29 B2 N2 102.1(3) C30 C29 B2 N2 -80.1(4) C34 C29 B2 C21 -77.4(4) C30 C29 B2 C21 100.4(3)