#------------------------------------------------------------------------------ #$Date: 2019-12-03 04:19:22 +0200 (Tue, 03 Dec 2019) $ #$Revision: 244871 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/64/1556413.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_1556413 loop_ _publ_author_name 'Wilson, Daniel' 'Franco, Mauricio P.' 'Myers, William' 'McGrady, John E.' 'Goicoechea, Jose M.' _publ_section_title ; Base induced isomerisation of a phosphaethynolato-borane: Mechanistic insights into boryl migration and decarbonylation to afford a triplet phosphinidene ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC05969E _journal_year 2020 _chemical_formula_moiety 'C36 H47 B N3 P' _chemical_formula_sum 'C36 H47 B N3 P' _chemical_formula_weight 563.54 _chemical_name_systematic ; [{(Mes)NC}P]B[{N(2,6-iPr-C6H3)}2(CH)2] ; _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-2018/1 _audit_update_record ; 2019-11-01 deposited with the CCDC. 2019-12-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.2900(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.9679(3) _cell_length_b 7.40540(10) _cell_length_c 25.1568(3) _cell_measurement_reflns_used 12087 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 76.4470 _cell_measurement_theta_min 2.4380 _cell_volume 3373.97(8) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_structure_refinement 'SHELXL-2018/1 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 10.4102 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator mirror _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_unetI/netI 0.0245 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_number 29145 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.577 _diffrn_reflns_theta_min 2.440 _exptl_absorpt_coefficient_mu 0.914 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.78558 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.109 _exptl_crystal_description block _exptl_crystal_F_000 1216 _exptl_crystal_size_max 0.440 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.120 _refine_diff_density_max 0.334 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 381 _refine_ls_number_reflns 7067 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0537 _refine_ls_R_factor_gt 0.0471 _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^)+(0.0592P)^2^+1.4943P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1227 _refine_ls_wR_factor_ref 0.1283 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6150 _reflns_number_total 7067 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05969e2.cif _cod_data_source_block DW357 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 1556413 _shelx_shelxl_version_number 2018/1 _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_estimated_absorpt_t_min 0.689 _shelx_estimated_absorpt_t_max 0.898 _shelx_res_file ; TITL DW357 in P2(1)/c shelx.res created by SHELXL-2018/1 at 13:48:55 on 28-Feb-2019 CELL 1.54184 18.9679 7.4054 25.1568 90.000 107.290 90.000 ZERR 4.00 0.0003 0.0001 0.0003 0.000 0.001 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H B N P UNIT 144 188 4 12 4 MERG 2 FMAP 2 53 53 PLAN 10 SIZE 0.120 0.200 0.440 ACTA BOND $H L.S. 48 TEMP -123.00 WGHT 0.059200 1.494300 FVAR 3.17100 P1 5 0.240632 0.563256 0.461293 11.00000 0.04127 0.01830 = 0.03039 0.00020 -0.00908 -0.00057 C1 1 0.281320 0.517107 0.528580 11.00000 0.02807 0.02189 = 0.03420 -0.00531 0.00115 0.00053 N1 4 0.305960 0.516470 0.578162 11.00000 0.03514 0.02893 = 0.02956 -0.00492 -0.00119 -0.00195 C2 1 0.369481 0.505430 0.624104 11.00000 0.03680 0.02221 = 0.02546 -0.00151 -0.00150 -0.00316 C3 1 0.438623 0.467712 0.617100 11.00000 0.03660 0.02180 = 0.03026 -0.00020 0.00081 -0.00092 C4 1 0.499756 0.469136 0.664495 11.00000 0.03712 0.02722 = 0.04281 -0.00138 -0.00383 0.00084 AFIX 43 H4 2 0.547167 0.444056 0.660747 11.00000 -1.20000 AFIX 0 C5 1 0.493434 0.506122 0.717037 11.00000 0.05238 0.02943 = 0.03432 -0.00155 -0.01137 0.00450 C6 1 0.424041 0.539209 0.722163 11.00000 0.06708 0.03206 = 0.02438 -0.00252 0.00097 0.00196 AFIX 43 H6 2 0.419274 0.561698 0.758114 11.00000 -1.20000 AFIX 0 C7 1 0.360996 0.540722 0.676549 11.00000 0.04812 0.02575 = 0.03107 -0.00261 0.00627 -0.00103 C8 1 0.446431 0.431063 0.560484 11.00000 0.03976 0.03302 = 0.03744 -0.00238 0.00808 0.00108 AFIX 137 H8A 2 0.498633 0.412179 0.563564 11.00000 -1.50000 H8B 2 0.427550 0.534379 0.536058 11.00000 -1.50000 H8C 2 0.418209 0.322683 0.544836 11.00000 -1.50000 AFIX 0 C9 1 0.560667 0.514038 0.767610 11.00000 0.07076 0.05195 = 0.04630 -0.00931 -0.02562 0.01343 AFIX 137 H9A 2 0.578744 0.638617 0.773483 11.00000 -1.50000 H9B 2 0.599416 0.436006 0.761743 11.00000 -1.50000 H9C 2 0.547439 0.472624 0.800398 11.00000 -1.50000 AFIX 0 C10 1 0.286979 0.586265 0.683094 11.00000 0.06015 0.04479 = 0.04512 -0.00951 0.01887 0.00009 AFIX 137 H10A 2 0.290479 0.588621 0.722746 11.00000 -1.50000 H10B 2 0.250856 0.494887 0.664150 11.00000 -1.50000 H10C 2 0.271238 0.705047 0.666663 11.00000 -1.50000 AFIX 0 B1 3 0.199229 0.334285 0.433499 11.00000 0.02165 0.01984 = 0.02002 0.00055 0.00136 0.00008 N3 4 0.217471 0.149505 0.446962 11.00000 0.02156 0.01907 = 0.02315 0.00130 -0.00070 0.00114 N2 4 0.137035 0.328399 0.384251 11.00000 0.02310 0.01966 = 0.02149 0.00058 -0.00072 0.00063 C12 1 0.167744 0.041108 0.407154 11.00000 0.02673 0.01929 = 0.03175 -0.00173 0.00055 -0.00225 AFIX 43 H12 2 0.167657 -0.087166 0.406655 11.00000 -1.20000 AFIX 0 C11 1 0.120430 0.147271 0.369979 11.00000 0.02540 0.02349 = 0.02722 -0.00293 -0.00078 -0.00352 AFIX 43 H11 2 0.081753 0.106054 0.338871 11.00000 -1.20000 AFIX 0 C25 1 0.280018 0.072497 0.487821 11.00000 0.02200 0.01609 = 0.02606 0.00158 -0.00037 0.00044 C26 1 0.341692 0.021934 0.471452 11.00000 0.02349 0.02111 = 0.03139 -0.00027 0.00229 -0.00105 C27 1 0.401854 -0.054115 0.511617 11.00000 0.02188 0.02620 = 0.04320 0.00116 0.00148 0.00193 AFIX 43 H27 2 0.444112 -0.090774 0.501490 11.00000 -1.20000 AFIX 0 C28 1 0.400613 -0.076598 0.565816 11.00000 0.02759 0.02844 = 0.03986 0.00790 -0.00600 0.00262 AFIX 43 H28 2 0.442153 -0.127104 0.592751 11.00000 -1.20000 AFIX 0 C29 1 0.339376 -0.026089 0.581003 11.00000 0.03585 0.02924 = 0.02715 0.00583 -0.00149 -0.00122 AFIX 43 H29 2 0.339376 -0.042180 0.618468 11.00000 -1.20000 AFIX 0 C30 1 0.277378 0.048187 0.542505 11.00000 0.02828 0.01935 = 0.02720 0.00137 0.00182 -0.00053 C31 1 0.345203 0.053153 0.412685 11.00000 0.02664 0.03997 = 0.03500 -0.00051 0.00795 0.00076 AFIX 13 H31 2 0.293423 0.060341 0.387442 11.00000 -1.20000 AFIX 0 C32 1 0.383279 0.232664 0.408984 11.00000 0.04092 0.04204 = 0.05038 0.00978 0.01765 0.00095 AFIX 137 H32A 2 0.356447 0.331147 0.420406 11.00000 -1.50000 H32B 2 0.383643 0.252650 0.370558 11.00000 -1.50000 H32C 2 0.434154 0.229260 0.433617 11.00000 -1.50000 AFIX 0 C33 1 0.384386 -0.100944 0.392019 11.00000 0.05630 0.05049 = 0.05248 -0.01172 0.02366 0.00095 AFIX 137 H33A 2 0.437293 -0.097701 0.411994 11.00000 -1.50000 H33B 2 0.377154 -0.086631 0.352023 11.00000 -1.50000 H33C 2 0.363736 -0.216915 0.398842 11.00000 -1.50000 AFIX 0 C34 1 0.208546 0.095735 0.558420 11.00000 0.03626 0.03106 = 0.03059 0.00294 0.00947 0.00429 AFIX 13 H34 2 0.187876 0.209795 0.538578 11.00000 -1.20000 AFIX 0 C35 1 0.223712 0.128416 0.620728 11.00000 0.06102 0.05111 = 0.03455 0.00067 0.01844 0.00637 AFIX 137 H35A 2 0.234799 0.013221 0.640647 11.00000 -1.50000 H35B 2 0.180110 0.182937 0.627530 11.00000 -1.50000 H35C 2 0.265963 0.210072 0.634009 11.00000 -1.50000 AFIX 0 C36 1 0.150179 -0.051533 0.539119 11.00000 0.04206 0.05545 = 0.06060 -0.01179 0.02519 -0.01122 AFIX 137 H36A 2 0.137045 -0.063816 0.498558 11.00000 -1.50000 H36B 2 0.106139 -0.018886 0.549743 11.00000 -1.50000 H36C 2 0.169891 -0.166419 0.556667 11.00000 -1.50000 AFIX 0 C13 1 0.103409 0.474132 0.348338 11.00000 0.03025 0.02217 = 0.02194 0.00104 -0.00796 -0.00235 C14 1 0.135037 0.526763 0.307055 11.00000 0.04472 0.05734 = 0.02882 0.01467 -0.00834 -0.02002 C15 1 0.100485 0.666121 0.271492 11.00000 0.08567 0.07199 = 0.04764 0.03805 -0.02964 -0.03963 AFIX 43 H15 2 0.120290 0.703429 0.242732 11.00000 -1.20000 AFIX 0 C16 1 0.039048 0.750177 0.276923 11.00000 0.11695 0.03059 = 0.06098 0.01519 -0.05525 -0.00584 AFIX 43 H16 2 0.015774 0.842636 0.251595 11.00000 -1.20000 AFIX 0 C17 1 0.011092 0.700722 0.319019 11.00000 0.07962 0.04141 = 0.05938 -0.01500 -0.03590 0.03119 AFIX 43 H17 2 -0.030532 0.763560 0.323327 11.00000 -1.20000 AFIX 0 C18 1 0.041813 0.560561 0.355948 11.00000 0.04289 0.03935 = 0.03473 -0.00995 -0.01254 0.01631 C19 1 0.204312 0.435611 0.301554 11.00000 0.04053 0.14537 = 0.03351 0.02441 0.00870 -0.01570 AFIX 13 H19 2 0.230010 0.379905 0.338441 11.00000 -1.20000 AFIX 0 C20 1 0.257991 0.567432 0.288352 11.00000 0.08380 0.27931 = 0.09067 0.01831 0.02600 -0.09538 AFIX 137 H20A 2 0.236876 0.614260 0.250507 11.00000 -1.50000 H20B 2 0.304583 0.505454 0.291076 11.00000 -1.50000 H20C 2 0.267192 0.667748 0.314942 11.00000 -1.50000 AFIX 0 C21 1 0.186808 0.283924 0.258819 11.00000 0.07024 0.17817 = 0.07784 -0.00603 0.04067 0.00843 AFIX 137 H21A 2 0.163113 0.334233 0.221772 11.00000 -1.50000 H21B 2 0.153406 0.197176 0.268281 11.00000 -1.50000 H21C 2 0.232632 0.222675 0.258881 11.00000 -1.50000 AFIX 0 C22 1 0.009671 0.507849 0.401532 11.00000 0.04250 0.09872 = 0.04444 -0.01487 0.00308 0.03041 AFIX 13 H22 2 0.046521 0.430890 0.428845 11.00000 -1.20000 AFIX 0 C23 1 -0.006665 0.673300 0.432377 11.00000 0.08090 0.16409 = 0.13436 -0.09972 0.04274 -0.00826 AFIX 137 H23A 2 0.039057 0.741167 0.448538 11.00000 -1.50000 H23B 2 -0.026822 0.634050 0.462116 11.00000 -1.50000 H23C 2 -0.042691 0.750629 0.406229 11.00000 -1.50000 AFIX 0 C24 1 -0.059793 0.399061 0.378378 11.00000 0.12300 0.11300 = 0.07666 -0.01870 0.04079 -0.03914 AFIX 137 H24A 2 -0.094057 0.465854 0.347842 11.00000 -1.50000 H24B 2 -0.082968 0.377244 0.407796 11.00000 -1.50000 H24C 2 -0.047555 0.283295 0.364429 11.00000 -1.50000 AFIX 0 HKLF 4 REM DW357 in P2(1)/c REM R1 = 0.0471 for 6150 Fo > 4sig(Fo) and 0.0537 for all 7067 data REM 381 parameters refined using 0 restraints END WGHT 0.0591 1.4961 REM Highest difference peak 0.334, deepest hole -0.321, 1-sigma level 0.042 Q1 1 0.2676 0.6027 0.3221 11.00000 0.05 0.33 Q2 1 0.2669 0.5127 0.2839 11.00000 0.05 0.31 Q3 1 0.2229 0.4452 0.4468 11.00000 0.05 0.30 Q4 1 0.5569 0.6143 0.7993 11.00000 0.05 0.30 Q5 1 0.1826 0.4021 0.2416 11.00000 0.05 0.27 Q6 1 -0.0637 0.2809 0.3656 11.00000 0.05 0.26 Q7 1 0.1207 0.2451 0.3786 11.00000 0.05 0.23 Q8 1 -0.0057 0.7219 0.4207 11.00000 0.05 0.23 Q9 1 0.3410 0.0248 0.4425 11.00000 0.05 0.23 Q10 1 0.1200 0.6109 0.2954 11.00000 0.05 0.23 ; _shelx_res_checksum 89906 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 P1 P 0.24063(2) 0.56326(5) 0.46129(2) 0.03428(12) Uani 1 1 d . . C1 C 0.28132(8) 0.51711(19) 0.52858(6) 0.0298(3) Uani 1 1 d . . N1 N 0.30596(7) 0.51647(18) 0.57816(5) 0.0336(3) Uani 1 1 d . . C2 C 0.36948(9) 0.50543(19) 0.62410(6) 0.0305(3) Uani 1 1 d . . C3 C 0.43862(9) 0.4677(2) 0.61710(6) 0.0315(3) Uani 1 1 d . . C4 C 0.49976(9) 0.4691(2) 0.66449(7) 0.0391(4) Uani 1 1 d . . H4 H 0.547167 0.444056 0.660747 0.047 Uiso 1 1 calc R U C5 C 0.49343(11) 0.5061(2) 0.71704(7) 0.0440(4) Uani 1 1 d . . C6 C 0.42404(11) 0.5392(2) 0.72216(7) 0.0439(4) Uani 1 1 d . . H6 H 0.419274 0.561698 0.758114 0.053 Uiso 1 1 calc R U C7 C 0.36100(10) 0.5407(2) 0.67655(7) 0.0362(3) Uani 1 1 d . . C8 C 0.44643(9) 0.4311(2) 0.56048(7) 0.0375(4) Uani 1 1 d . . H8A H 0.498633 0.412179 0.563564 0.056 Uiso 1 1 calc R U H8B H 0.427550 0.534379 0.536058 0.056 Uiso 1 1 calc R U H8C H 0.418209 0.322683 0.544836 0.056 Uiso 1 1 calc R U C9 C 0.56067(13) 0.5140(3) 0.76761(9) 0.0657(7) Uani 1 1 d . . H9A H 0.578744 0.638617 0.773483 0.099 Uiso 1 1 calc R U H9B H 0.599416 0.436006 0.761743 0.099 Uiso 1 1 calc R U H9C H 0.547439 0.472624 0.800398 0.099 Uiso 1 1 calc R U C10 C 0.28698(12) 0.5863(3) 0.68309(8) 0.0493(4) Uani 1 1 d . . H10A H 0.290479 0.588621 0.722746 0.074 Uiso 1 1 calc R U H10B H 0.250856 0.494887 0.664150 0.074 Uiso 1 1 calc R U H10C H 0.271238 0.705047 0.666663 0.074 Uiso 1 1 calc R U B1 B 0.19923(8) 0.3343(2) 0.43350(6) 0.0216(3) Uani 1 1 d . . N3 N 0.21747(6) 0.14951(15) 0.44696(5) 0.0229(2) Uani 1 1 d . . N2 N 0.13703(6) 0.32840(15) 0.38425(5) 0.0230(2) Uani 1 1 d . . C12 C 0.16774(8) 0.04111(19) 0.40715(6) 0.0277(3) Uani 1 1 d . . H12 H 0.167657 -0.087166 0.406655 0.033 Uiso 1 1 calc R U C11 C 0.12043(8) 0.14727(19) 0.36998(6) 0.0272(3) Uani 1 1 d . . H11 H 0.081753 0.106054 0.338871 0.033 Uiso 1 1 calc R U C25 C 0.28002(7) 0.07250(17) 0.48782(6) 0.0230(3) Uani 1 1 d . . C26 C 0.34169(8) 0.02193(19) 0.47145(6) 0.0266(3) Uani 1 1 d . . C27 C 0.40185(8) -0.0541(2) 0.51162(7) 0.0322(3) Uani 1 1 d . . H27 H 0.444112 -0.090774 0.501490 0.039 Uiso 1 1 calc R U C28 C 0.40061(8) -0.0766(2) 0.56582(7) 0.0354(4) Uani 1 1 d . . H28 H 0.442153 -0.127104 0.592751 0.043 Uiso 1 1 calc R U C29 C 0.33938(9) -0.0261(2) 0.58100(6) 0.0331(3) Uani 1 1 d . . H29 H 0.339376 -0.042180 0.618468 0.040 Uiso 1 1 calc R U C30 C 0.27738(8) 0.04819(18) 0.54251(6) 0.0263(3) Uani 1 1 d . . C31 C 0.34520(8) 0.0532(2) 0.41269(7) 0.0341(3) Uani 1 1 d . . H31 H 0.293423 0.060341 0.387442 0.041 Uiso 1 1 calc R U C32 C 0.38328(10) 0.2327(2) 0.40898(8) 0.0436(4) Uani 1 1 d . . H32A H 0.356447 0.331147 0.420406 0.065 Uiso 1 1 calc R U H32B H 0.383643 0.252650 0.370558 0.065 Uiso 1 1 calc R U H32C H 0.434154 0.229260 0.433617 0.065 Uiso 1 1 calc R U C33 C 0.38439(12) -0.1009(3) 0.39202(9) 0.0515(5) Uani 1 1 d . . H33A H 0.437293 -0.097701 0.411994 0.077 Uiso 1 1 calc R U H33B H 0.377154 -0.086631 0.352023 0.077 Uiso 1 1 calc R U H33C H 0.363736 -0.216915 0.398842 0.077 Uiso 1 1 calc R U C34 C 0.20855(9) 0.0957(2) 0.55842(6) 0.0327(3) Uani 1 1 d . . H34 H 0.187876 0.209795 0.538578 0.039 Uiso 1 1 calc R U C35 C 0.22371(12) 0.1284(3) 0.62073(7) 0.0480(4) Uani 1 1 d . . H35A H 0.234799 0.013221 0.640647 0.072 Uiso 1 1 calc R U H35B H 0.180110 0.182937 0.627530 0.072 Uiso 1 1 calc R U H35C H 0.265963 0.210072 0.634009 0.072 Uiso 1 1 calc R U C36 C 0.15018(11) -0.0515(3) 0.53912(9) 0.0505(5) Uani 1 1 d . . H36A H 0.137045 -0.063816 0.498558 0.076 Uiso 1 1 calc R U H36B H 0.106139 -0.018886 0.549743 0.076 Uiso 1 1 calc R U H36C H 0.169891 -0.166419 0.556667 0.076 Uiso 1 1 calc R U C13 C 0.10341(8) 0.47413(19) 0.34834(6) 0.0282(3) Uani 1 1 d . . C14 C 0.13504(10) 0.5268(3) 0.30706(7) 0.0478(5) Uani 1 1 d . . C15 C 0.10049(15) 0.6661(4) 0.27149(9) 0.0792(9) Uani 1 1 d . . H15 H 0.120290 0.703429 0.242732 0.095 Uiso 1 1 calc R U C16 C 0.03905(18) 0.7502(3) 0.27692(11) 0.0873(11) Uani 1 1 d . . H16 H 0.015774 0.842636 0.251595 0.105 Uiso 1 1 calc R U C17 C 0.01109(14) 0.7007(3) 0.31902(10) 0.0724(8) Uani 1 1 d . . H17 H -0.030532 0.763560 0.323327 0.087 Uiso 1 1 calc R U C18 C 0.04181(10) 0.5606(2) 0.35595(7) 0.0442(4) Uani 1 1 d . . C19 C 0.20431(11) 0.4356(5) 0.30155(9) 0.0736(9) Uani 1 1 d . . H19 H 0.230010 0.379905 0.338441 0.088 Uiso 1 1 calc R U C20 C 0.2580(2) 0.5674(8) 0.28835(16) 0.151(2) Uani 1 1 d . . H20A H 0.236876 0.614260 0.250507 0.227 Uiso 1 1 calc R U H20B H 0.304583 0.505454 0.291076 0.227 Uiso 1 1 calc R U H20C H 0.267192 0.667748 0.314942 0.227 Uiso 1 1 calc R U C21 C 0.18681(17) 0.2839(6) 0.25882(13) 0.1047(12) Uani 1 1 d . . H21A H 0.163113 0.334233 0.221772 0.157 Uiso 1 1 calc R U H21B H 0.153406 0.197176 0.268281 0.157 Uiso 1 1 calc R U H21C H 0.232632 0.222675 0.258881 0.157 Uiso 1 1 calc R U C22 C 0.00967(11) 0.5078(4) 0.40153(9) 0.0640(7) Uani 1 1 d . . H22 H 0.046521 0.430890 0.428845 0.077 Uiso 1 1 calc R U C23 C -0.00667(18) 0.6733(6) 0.43238(16) 0.1241(16) Uani 1 1 d . . H23A H 0.039057 0.741167 0.448538 0.186 Uiso 1 1 calc R U H23B H -0.026822 0.634050 0.462116 0.186 Uiso 1 1 calc R U H23C H -0.042691 0.750629 0.406229 0.186 Uiso 1 1 calc R U C24 C -0.0598(2) 0.3991(5) 0.37838(14) 0.1018(11) Uani 1 1 d . . H24A H -0.094057 0.465854 0.347842 0.153 Uiso 1 1 calc R U H24B H -0.082968 0.377244 0.407796 0.153 Uiso 1 1 calc R U H24C H -0.047555 0.283295 0.364429 0.153 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 P1 0.0413(2) 0.01830(18) 0.0304(2) 0.00020(13) -0.00908(16) -0.00057(14) C1 0.0281(7) 0.0219(6) 0.0342(8) -0.0053(6) 0.0011(6) 0.0005(5) N1 0.0351(7) 0.0289(6) 0.0296(7) -0.0049(5) -0.0012(5) -0.0020(5) C2 0.0368(8) 0.0222(6) 0.0255(7) -0.0015(5) -0.0015(6) -0.0032(6) C3 0.0366(8) 0.0218(6) 0.0303(7) -0.0002(5) 0.0008(6) -0.0009(6) C4 0.0371(8) 0.0272(7) 0.0428(9) -0.0014(6) -0.0038(7) 0.0008(6) C5 0.0524(10) 0.0294(8) 0.0343(9) -0.0015(6) -0.0114(7) 0.0045(7) C6 0.0671(12) 0.0321(8) 0.0244(7) -0.0025(6) 0.0010(8) 0.0020(8) C7 0.0481(9) 0.0258(7) 0.0311(8) -0.0026(6) 0.0063(7) -0.0010(7) C8 0.0398(8) 0.0330(8) 0.0374(8) -0.0024(6) 0.0081(7) 0.0011(7) C9 0.0708(14) 0.0519(12) 0.0463(11) -0.0093(9) -0.0256(10) 0.0134(11) C10 0.0602(12) 0.0448(10) 0.0451(10) -0.0095(8) 0.0189(9) 0.0001(9) B1 0.0216(7) 0.0198(7) 0.0200(7) 0.0005(5) 0.0014(5) 0.0001(5) N3 0.0216(5) 0.0191(5) 0.0231(5) 0.0013(4) -0.0007(4) 0.0011(4) N2 0.0231(5) 0.0197(5) 0.0215(5) 0.0006(4) -0.0007(4) 0.0006(4) C12 0.0267(7) 0.0193(6) 0.0318(7) -0.0017(5) 0.0006(6) -0.0022(5) C11 0.0254(6) 0.0235(7) 0.0272(7) -0.0029(5) -0.0008(5) -0.0035(5) C25 0.0220(6) 0.0161(6) 0.0261(7) 0.0016(5) -0.0004(5) 0.0004(5) C26 0.0235(6) 0.0211(6) 0.0314(7) -0.0003(5) 0.0023(5) -0.0010(5) C27 0.0219(6) 0.0262(7) 0.0432(9) 0.0012(6) 0.0015(6) 0.0019(5) C28 0.0276(7) 0.0284(7) 0.0399(8) 0.0079(6) -0.0060(6) 0.0026(6) C29 0.0359(8) 0.0292(7) 0.0271(7) 0.0058(6) -0.0015(6) -0.0012(6) C30 0.0283(7) 0.0194(6) 0.0272(7) 0.0014(5) 0.0018(5) -0.0005(5) C31 0.0266(7) 0.0400(9) 0.0350(8) -0.0005(6) 0.0079(6) 0.0008(6) C32 0.0409(9) 0.0420(9) 0.0504(10) 0.0098(8) 0.0177(8) 0.0010(7) C33 0.0563(11) 0.0505(11) 0.0525(11) -0.0117(9) 0.0237(9) 0.0009(9) C34 0.0363(8) 0.0311(7) 0.0306(8) 0.0029(6) 0.0095(6) 0.0043(6) C35 0.0610(11) 0.0511(11) 0.0345(9) 0.0007(8) 0.0184(8) 0.0064(9) C36 0.0421(10) 0.0555(11) 0.0606(12) -0.0118(9) 0.0252(9) -0.0112(8) C13 0.0302(7) 0.0222(6) 0.0219(6) 0.0010(5) -0.0080(5) -0.0023(5) C14 0.0447(9) 0.0573(11) 0.0288(8) 0.0147(8) -0.0083(7) -0.0200(9) C15 0.0857(17) 0.0720(16) 0.0476(12) 0.0380(12) -0.0296(12) -0.0396(14) C16 0.117(2) 0.0306(10) 0.0610(15) 0.0152(9) -0.0553(16) -0.0058(12) C17 0.0796(16) 0.0414(11) 0.0594(14) -0.0150(10) -0.0359(12) 0.0312(11) C18 0.0429(9) 0.0393(9) 0.0347(8) -0.0100(7) -0.0125(7) 0.0163(7) C19 0.0405(10) 0.145(3) 0.0335(10) 0.0244(13) 0.0087(8) -0.0157(13) C20 0.084(2) 0.279(6) 0.091(2) 0.018(3) 0.0260(19) -0.095(3) C21 0.0702(17) 0.178(4) 0.0778(19) -0.006(2) 0.0407(15) 0.008(2) C22 0.0425(10) 0.0987(18) 0.0444(11) -0.0149(11) 0.0031(8) 0.0304(11) C23 0.081(2) 0.164(4) 0.134(3) -0.100(3) 0.043(2) -0.008(2) C24 0.123(3) 0.113(3) 0.0767(19) -0.0187(18) 0.0408(19) -0.039(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 P1 B1 101.81(7) N1 C1 P1 167.50(13) C1 N1 C2 146.54(16) C7 C2 N1 117.03(15) C7 C2 C3 121.95(14) N1 C2 C3 120.97(14) C4 C3 C2 117.53(15) C4 C3 C8 121.44(16) C2 C3 C8 121.02(14) C5 C4 C3 122.00(17) C5 C4 H4 119.0 C3 C4 H4 119.0 C6 C5 C4 118.52(15) C6 C5 C9 120.22(18) C4 C5 C9 121.2(2) C5 C6 C7 122.28(17) C5 C6 H6 118.9 C7 C6 H6 118.9 C6 C7 C2 117.70(17) C6 C7 C10 121.00(16) C2 C7 C10 121.26(15) C3 C8 H8A 109.5 C3 C8 H8B 109.5 H8A C8 H8B 109.5 C3 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C5 C9 H9A 109.5 C5 C9 H9B 109.5 H9A C9 H9B 109.5 C5 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C7 C10 H10A 109.5 C7 C10 H10B 109.5 H10A C10 H10B 109.5 C7 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 N3 B1 N2 104.76(11) N3 B1 P1 136.00(10) N2 B1 P1 119.05(10) C12 N3 B1 108.33(11) C12 N3 C25 121.31(11) B1 N3 C25 129.84(11) C11 N2 C13 122.47(11) C11 N2 B1 108.36(11) C13 N2 B1 128.34(11) C11 C12 N3 109.29(12) C11 C12 H12 125.4 N3 C12 H12 125.4 C12 C11 N2 109.26(12) C12 C11 H11 125.4 N2 C11 H11 125.4 C26 C25 C30 122.00(12) C26 C25 N3 118.66(12) C30 C25 N3 119.33(12) C27 C26 C25 117.93(14) C27 C26 C31 120.18(14) C25 C26 C31 121.85(12) C28 C27 C26 120.83(14) C28 C27 H27 119.6 C26 C27 H27 119.6 C29 C28 C27 120.28(13) C29 C28 H28 119.9 C27 C28 H28 119.9 C28 C29 C30 121.37(15) C28 C29 H29 119.3 C30 C29 H29 119.3 C29 C30 C25 117.57(14) C29 C30 C34 121.50(14) C25 C30 C34 120.90(12) C26 C31 C32 110.50(14) C26 C31 C33 112.50(14) C32 C31 C33 109.93(15) C26 C31 H31 107.9 C32 C31 H31 107.9 C33 C31 H31 107.9 C31 C32 H32A 109.5 C31 C32 H32B 109.5 H32A C32 H32B 109.5 C31 C32 H32C 109.5 H32A C32 H32C 109.5 H32B C32 H32C 109.5 C31 C33 H33A 109.5 C31 C33 H33B 109.5 H33A C33 H33B 109.5 C31 C33 H33C 109.5 H33A C33 H33C 109.5 H33B C33 H33C 109.5 C30 C34 C35 113.18(13) C30 C34 C36 110.49(13) C35 C34 C36 109.71(15) C30 C34 H34 107.8 C35 C34 H34 107.8 C36 C34 H34 107.8 C34 C35 H35A 109.5 C34 C35 H35B 109.5 H35A C35 H35B 109.5 C34 C35 H35C 109.5 H35A C35 H35C 109.5 H35B C35 H35C 109.5 C34 C36 H36A 109.5 C34 C36 H36B 109.5 H36A C36 H36B 109.5 C34 C36 H36C 109.5 H36A C36 H36C 109.5 H36B C36 H36C 109.5 C18 C13 C14 122.36(16) C18 C13 N2 119.62(14) C14 C13 N2 118.01(15) C15 C14 C13 117.3(2) C15 C14 C19 121.6(2) C13 C14 C19 121.10(16) C16 C15 C14 121.7(2) C16 C15 H15 119.1 C14 C15 H15 119.1 C15 C16 C17 119.67(18) C15 C16 H16 120.2 C17 C16 H16 120.2 C16 C17 C18 122.1(2) C16 C17 H17 118.9 C18 C17 H17 118.9 C13 C18 C17 116.7(2) C13 C18 C22 122.17(16) C17 C18 C22 121.1(2) C20 C19 C14 112.9(3) C20 C19 C21 109.9(3) C14 C19 C21 112.28(19) C20 C19 H19 107.2 C14 C19 H19 107.2 C21 C19 H19 107.2 C19 C20 H20A 109.5 C19 C20 H20B 109.5 H20A C20 H20B 109.5 C19 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C19 C21 H21A 109.5 C19 C21 H21B 109.5 H21A C21 H21B 109.5 C19 C21 H21C 109.5 H21A C21 H21C 109.5 H21B C21 H21C 109.5 C18 C22 C24 110.54(19) C18 C22 C23 111.6(3) C24 C22 C23 109.8(2) C18 C22 H22 108.3 C24 C22 H22 108.3 C23 C22 H22 108.3 C22 C23 H23A 109.5 C22 C23 H23B 109.5 H23A C23 H23B 109.5 C22 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 C22 C24 H24A 109.5 C22 C24 H24B 109.5 H24A C24 H24B 109.5 C22 C24 H24C 109.5 H24A C24 H24C 109.5 H24B C24 H24C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 C1 1.6737(16) P1 B1 1.9116(15) C1 N1 1.195(2) N1 C2 1.4023(18) C2 C7 1.400(2) C2 C3 1.402(2) C3 C4 1.394(2) C3 C8 1.500(2) C4 C5 1.390(3) C4 H4 0.9500 C5 C6 1.382(3) C5 C9 1.511(2) C6 C7 1.390(2) C6 H6 0.9500 C7 C10 1.500(3) C8 H8A 0.9800 C8 H8B 0.9800 C8 H8C 0.9800 C9 H9A 0.9800 C9 H9B 0.9800 C9 H9C 0.9800 C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 B1 N3 1.4273(18) B1 N2 1.4352(17) N3 C12 1.4055(17) N3 C25 1.4368(16) N2 C11 1.4000(17) N2 C13 1.4301(17) C12 C11 1.341(2) C12 H12 0.9500 C11 H11 0.9500 C25 C26 1.402(2) C25 C30 1.403(2) C26 C27 1.3982(19) C26 C31 1.517(2) C27 C28 1.381(2) C27 H27 0.9500 C28 C29 1.378(2) C28 H28 0.9500 C29 C30 1.3952(19) C29 H29 0.9500 C30 C34 1.516(2) C31 C32 1.529(2) C31 C33 1.534(2) C31 H31 1.0000 C32 H32A 0.9800 C32 H32B 0.9800 C32 H32C 0.9800 C33 H33A 0.9800 C33 H33B 0.9800 C33 H33C 0.9800 C34 C35 1.527(2) C34 C36 1.527(2) C34 H34 1.0000 C35 H35A 0.9800 C35 H35B 0.9800 C35 H35C 0.9800 C36 H36A 0.9800 C36 H36B 0.9800 C36 H36C 0.9800 C13 C18 1.394(2) C13 C14 1.400(2) C14 C15 1.395(3) C14 C19 1.520(3) C15 C16 1.363(5) C15 H15 0.9500 C16 C17 1.368(4) C16 H16 0.9500 C17 C18 1.399(3) C17 H17 0.9500 C18 C22 1.502(3) C19 C20 1.517(4) C19 C21 1.522(5) C19 H19 1.0000 C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 C21 H21A 0.9800 C21 H21B 0.9800 C21 H21C 0.9800 C22 C24 1.506(4) C22 C23 1.530(4) C22 H22 1.0000 C23 H23A 0.9800 C23 H23B 0.9800 C23 H23C 0.9800 C24 H24A 0.9800 C24 H24B 0.9800 C24 H24C 0.9800