#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:18:14 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247648 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/64/1556415.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_1556415 loop_ _publ_author_name 'Wilson, Daniel W. N.' 'Franco, Mauricio P.' 'Myers, William K.' '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_issue 3 _journal_name_full 'Chemical Science' _journal_page_first 862 _journal_paper_doi 10.1039/C9SC05969E _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C27 H36 B N2 O P' _chemical_formula_sum 'C27 H36 B N2 O P' _chemical_formula_weight 446.36 _chemical_name_systematic ; (OCP)B[{N(2,6-iPr-C6H3)}2(CH)2] ; _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-2018/1 _audit_update_record ; 2019-11-01 deposited with the CCDC. 2019-12-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.1770(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.39040(10) _cell_length_b 14.20380(10) _cell_length_c 20.3914(2) _cell_measurement_reflns_used 11024 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 76.1970 _cell_measurement_theta_min 3.8030 _cell_volume 2684.98(4) _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 0.993 _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 0.0212 _diffrn_reflns_av_unetI/netI 0.0181 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 20355 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.522 _diffrn_reflns_theta_min 3.809 _exptl_absorpt_coefficient_mu 1.046 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92302 _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 colourless _exptl_crystal_density_diffrn 1.104 _exptl_crystal_description block _exptl_crystal_F_000 960 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.200 _refine_diff_density_max 0.294 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 327 _refine_ls_number_reflns 5608 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0400 _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^)+(0.0556P)^2^+0.7801P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1051 _refine_ls_wR_factor_ref 0.1106 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4928 _reflns_number_total 5608 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc05969e2.cif _cod_data_source_block DW368 _cod_depositor_comments 'Adding full bibliography for 1556409--1556415.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1556415 _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 0.731 _shelx_estimated_absorpt_t_max 0.818 _shelx_res_file ; TITL p21n in P2(1)/n shelx.res created by SHELXL-2018/1 at 16:38:10 on 28-Feb-2019 CELL 1.54184 9.3904 14.2038 20.3914 90.000 99.177 90.000 ZERR 4.00 0.0001 0.0001 0.0002 0.000 0.001 0.000 LATT 1 SYMM 1/2 - X, 1/2 + Y, 1/2 - Z SFAC C H B N O P UNIT 108 144 4 8 4 4 MERG 2 FMAP 2 PLAN 20 SIZE 0.200 0.220 0.320 ACTA BOND $H L.S. 24 TEMP -123.00 WGHT 0.055600 0.780100 FVAR 0.46803 0.51446 P1 6 0.615854 0.343514 0.232741 11.00000 0.05288 0.04670 = 0.03151 -0.00739 -0.00197 0.02542 C1 1 0.557480 0.352375 0.152144 11.00000 0.06161 0.04100 = 0.03524 -0.00199 0.01158 0.02320 O1 5 0.528494 0.348513 0.095116 11.00000 0.13205 0.08332 = 0.03043 -0.00123 0.01121 0.06194 B1 3 0.501154 0.440406 0.263350 11.00000 0.02938 0.02673 = 0.02483 -0.00186 0.00400 0.00111 N2 4 0.389303 0.500127 0.231687 11.00000 0.02949 0.02896 = 0.02527 -0.00208 0.00399 0.00483 N1 4 0.519964 0.464478 0.331868 11.00000 0.03210 0.02940 = 0.02337 -0.00140 0.00409 0.00070 C2 1 0.420495 0.535080 0.340057 11.00000 0.04034 0.03693 = 0.02894 -0.00644 0.01025 0.00395 AFIX 43 H2 2 0.409101 0.563301 0.381139 11.00000 -1.20000 AFIX 0 C3 1 0.343623 0.556671 0.280644 11.00000 0.03622 0.03554 = 0.03370 -0.00504 0.00902 0.00893 AFIX 43 H3 2 0.269873 0.603002 0.273022 11.00000 -1.20000 AFIX 0 C4 1 0.621359 0.426847 0.385560 11.00000 0.03329 0.03104 = 0.02204 -0.00271 0.00123 -0.00336 C5 1 0.765720 0.457768 0.394082 11.00000 0.03620 0.03565 = 0.03004 -0.00662 0.00354 -0.00800 C6 1 0.860950 0.419726 0.446622 11.00000 0.03587 0.05213 = 0.04231 -0.00957 -0.00705 -0.00757 AFIX 43 H6 2 0.958835 0.439527 0.453728 11.00000 -1.20000 AFIX 0 C7 1 0.816052 0.353764 0.488650 11.00000 0.05442 0.05756 = 0.03692 0.00373 -0.01755 -0.00274 AFIX 43 H7 2 0.882502 0.329438 0.524688 11.00000 -1.20000 AFIX 0 C8 1 0.675035 0.323144 0.478425 11.00000 0.05986 0.05252 = 0.03302 0.01211 -0.00480 -0.01037 AFIX 43 H8 2 0.645619 0.277093 0.507291 11.00000 -1.20000 AFIX 0 C9 1 0.574831 0.358491 0.426529 11.00000 0.04029 0.04161 = 0.02631 0.00206 0.00076 -0.00945 C10 1 0.813891 0.531085 0.348052 11.00000 0.04475 0.04690 = 0.03862 -0.00509 0.01176 -0.01829 AFIX 13 H10 2 0.756352 0.520923 0.302953 11.00000 -1.20000 AFIX 0 C11 1 0.973949 0.522851 0.341246 11.00000 0.05675 0.08459 = 0.08404 -0.01184 0.03473 -0.02563 AFIX 137 H11A 2 1.033655 0.535774 0.384257 11.00000 -1.50000 H11B 2 0.996543 0.568476 0.308349 11.00000 -1.50000 H11C 2 0.993787 0.459047 0.326790 11.00000 -1.50000 AFIX 0 C12 1 0.780614 0.629787 0.370120 11.00000 0.08677 0.04080 = 0.07139 -0.00063 0.03163 -0.02101 AFIX 137 H12A 2 0.678124 0.634182 0.373968 11.00000 -1.50000 H12B 2 0.803062 0.675587 0.337303 11.00000 -1.50000 H12C 2 0.839202 0.643230 0.413315 11.00000 -1.50000 AFIX 0 C13 1 0.422528 0.319024 0.413862 11.00000 0.04133 0.05237 = 0.03744 0.00580 0.00690 -0.01465 AFIX 13 H13 2 0.366995 0.355046 0.376048 11.00000 -1.20000 AFIX 0 C14 1 0.425672 0.216038 0.392680 11.00000 0.05103 0.05616 = 0.09209 -0.00677 0.01118 -0.02367 AFIX 137 H14A 2 0.470563 0.211205 0.352596 11.00000 -1.50000 H14B 2 0.326897 0.191630 0.383367 11.00000 -1.50000 H14C 2 0.481574 0.179177 0.428481 11.00000 -1.50000 AFIX 0 C15 1 0.345578 0.331455 0.473843 11.00000 0.06069 0.10732 = 0.05667 -0.00243 0.02288 -0.01710 AFIX 137 H15A 2 0.397414 0.296444 0.511703 11.00000 -1.50000 H15B 2 0.246741 0.307487 0.463113 11.00000 -1.50000 H15C 2 0.343188 0.398412 0.485211 11.00000 -1.50000 AFIX 0 C16 1 0.346210 0.514151 0.161826 11.00000 0.02953 0.02780 = 0.02630 -0.00006 0.00205 0.00870 C17 1 0.429594 0.574516 0.128743 11.00000 0.03285 0.03201 = 0.03337 0.00323 0.00535 0.00825 C18 1 0.395463 0.580564 0.059868 11.00000 0.04961 0.04406 = 0.03497 0.00829 0.00999 0.01012 AFIX 43 H18 2 0.450721 0.620216 0.036060 11.00000 -1.20000 AFIX 0 C19 1 0.282075 0.529474 0.025865 11.00000 0.06138 0.05313 = 0.02513 0.00155 0.00000 0.01506 AFIX 43 H19 2 0.261661 0.533039 -0.021221 11.00000 -1.20000 AFIX 0 C20 1 0.198122 0.473311 0.059536 11.00000 0.04669 0.04347 = 0.03606 -0.00736 -0.00731 0.00663 AFIX 43 H20 2 0.118717 0.440216 0.035375 11.00000 -1.20000 AFIX 0 C21 1 0.227882 0.464296 0.128497 11.00000 0.03324 0.03077 = 0.03401 -0.00314 -0.00044 0.00622 C22 1 0.550350 0.633937 0.166357 11.00000 0.03451 0.03984 = 0.04606 0.00577 0.00534 -0.00118 AFIX 13 H22 2 0.566496 0.612031 0.213567 11.00000 -1.20000 AFIX 0 C23 1 0.691898 0.622545 0.140093 11.00000 0.03738 0.08745 = 0.10497 -0.01879 0.02073 -0.00425 AFIX 137 H23A 2 0.718941 0.555858 0.141165 11.00000 -1.50000 H23B 2 0.767410 0.658756 0.167889 11.00000 -1.50000 H23C 2 0.680674 0.645672 0.094278 11.00000 -1.50000 AFIX 0 C24 1 0.505984 0.736958 0.166299 11.00000 0.05313 0.04092 = 0.08414 -0.00780 0.00097 -0.00382 AFIX 137 H24A 2 0.486519 0.760141 0.120478 11.00000 -1.50000 H24B 2 0.584083 0.773939 0.191672 11.00000 -1.50000 H24C 2 0.418772 0.743154 0.186711 11.00000 -1.50000 AFIX 0 PART 1 C25 1 0.142304 0.402590 0.163422 21.00000 0.02715 0.05311 = 0.04140 -0.01091 -0.00262 0.00312 AFIX 13 H25 2 0.155363 0.424656 0.210570 21.00000 -1.20000 AFIX 0 C26 1 0.183995 0.299462 0.165066 21.00000 0.05867 0.03855 = 0.05946 0.00582 0.00323 -0.00675 AFIX 137 H26A 2 0.178107 0.275936 0.119534 21.00000 -1.50000 H26B 2 0.117961 0.263509 0.188169 21.00000 -1.50000 H26C 2 0.282882 0.292241 0.188560 21.00000 -1.50000 AFIX 0 C27 1 -0.025391 0.408257 0.135599 21.00000 0.03634 0.06828 = 0.12368 0.01386 0.00107 -0.00241 AFIX 137 H27A 2 -0.055208 0.474382 0.131301 21.00000 -1.50000 H27B 2 -0.079476 0.376152 0.166341 21.00000 -1.50000 H27C 2 -0.044949 0.377733 0.091989 21.00000 -1.50000 AFIX 0 PART 2 C25A 1 0.128667 0.404383 0.168659 -21.00000 0.03912 0.03078 = 0.04303 -0.00008 0.01342 -0.01058 AFIX 13 H25A 2 0.176804 0.401684 0.216041 -21.00000 -1.20000 AFIX 0 C26A 1 0.118764 0.303877 0.141351 -21.00000 0.10747 0.04946 = 0.09872 -0.02024 0.04692 -0.02658 AFIX 137 H26D 2 0.070354 0.263675 0.170064 -21.00000 -1.50000 H26E 2 0.216061 0.279682 0.140180 -21.00000 -1.50000 H26F 2 0.063533 0.303887 0.096316 -21.00000 -1.50000 AFIX 0 C27A 1 -0.010269 0.451015 0.166755 -21.00000 0.04453 0.08556 = 0.06472 0.00603 0.01509 0.00351 AFIX 137 H27D 2 0.004812 0.514110 0.186061 -21.00000 -1.50000 H27E 2 -0.070527 0.414164 0.192336 -21.00000 -1.50000 H27F 2 -0.058469 0.456111 0.120589 -21.00000 -1.50000 AFIX 0 HKLF 4 REM p21n in P2(1)/n REM R1 = 0.0400 for 4928 Fo > 4sig(Fo) and 0.0459 for all 5608 data REM 327 parameters refined using 0 restraints END WGHT 0.0517 0.8005 REM Highest difference peak 0.294, deepest hole -0.400, 1-sigma level 0.042 Q1 1 0.5341 0.3188 0.2343 11.00000 0.05 0.29 Q2 1 0.4988 0.3431 0.4204 11.00000 0.05 0.22 Q3 1 0.6104 0.3806 0.1132 11.00000 0.05 0.21 Q4 1 0.2793 0.4977 0.1457 11.00000 0.05 0.18 Q5 1 0.4613 0.3127 0.1159 11.00000 0.05 0.16 Q6 1 0.6183 0.3451 0.4503 11.00000 0.05 0.15 Q7 1 0.6865 0.4563 0.3995 11.00000 0.05 0.15 Q8 1 0.3696 0.5630 0.1476 11.00000 0.05 0.15 Q9 1 0.4883 0.6058 0.1467 11.00000 0.05 0.15 Q10 1 0.5781 0.4434 0.3601 11.00000 0.05 0.15 Q11 1 0.5901 0.4149 0.4208 11.00000 0.05 0.14 Q12 1 0.6965 0.4399 0.3871 11.00000 0.05 0.14 Q13 1 0.3575 0.5241 0.2507 11.00000 0.05 0.14 Q14 1 0.4182 0.4616 0.2437 11.00000 0.05 0.14 Q15 1 0.7813 0.4964 0.3710 11.00000 0.05 0.14 Q16 1 0.5517 0.4043 0.2464 11.00000 0.05 0.13 Q17 1 0.2366 0.5798 0.2565 11.00000 0.05 0.13 Q18 1 0.9606 0.5755 0.2892 11.00000 0.05 0.13 Q19 1 0.3632 0.5073 0.1974 11.00000 0.05 0.13 Q20 1 0.4185 0.7639 0.1484 11.00000 0.05 0.12 ; _shelx_res_checksum 36429 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 P1 P 0.61585(4) 0.34351(3) 0.23274(2) 0.04465(12) Uani 1 1 d . . . . . C1 C 0.55748(18) 0.35238(11) 0.15214(7) 0.0455(4) Uani 1 1 d . . . . . O1 O 0.52849(18) 0.34851(10) 0.09512(6) 0.0821(5) Uani 1 1 d . . . . . B1 B 0.50115(14) 0.44041(9) 0.26335(6) 0.0270(3) Uani 1 1 d . . . . . N2 N 0.38930(10) 0.50013(7) 0.23169(5) 0.0279(2) Uani 1 1 d . . . . . N1 N 0.51996(11) 0.46448(7) 0.33187(5) 0.0283(2) Uani 1 1 d . . . . . C2 C 0.42050(14) 0.53508(9) 0.34006(6) 0.0349(3) Uani 1 1 d . . . . . H2 H 0.409101 0.563301 0.381139 0.042 Uiso 1 1 calc R U . . . C3 C 0.34362(14) 0.55667(9) 0.28064(6) 0.0348(3) Uani 1 1 d . . . . . H3 H 0.269873 0.603002 0.273022 0.042 Uiso 1 1 calc R U . . . C4 C 0.62136(13) 0.42685(9) 0.38556(6) 0.0291(2) Uani 1 1 d . . . . . C5 C 0.76572(14) 0.45777(9) 0.39408(6) 0.0341(3) Uani 1 1 d . . . . . C6 C 0.86095(15) 0.41973(11) 0.44662(7) 0.0449(3) Uani 1 1 d . . . . . H6 H 0.958835 0.439527 0.453728 0.054 Uiso 1 1 calc R U . . . C7 C 0.81605(18) 0.35376(12) 0.48865(8) 0.0523(4) Uani 1 1 d . . . . . H7 H 0.882502 0.329438 0.524688 0.063 Uiso 1 1 calc R U . . . C8 C 0.67504(18) 0.32314(12) 0.47842(7) 0.0498(4) Uani 1 1 d . . . . . H8 H 0.645619 0.277093 0.507291 0.060 Uiso 1 1 calc R U . . . C9 C 0.57483(14) 0.35849(10) 0.42653(6) 0.0366(3) Uani 1 1 d . . . . . C10 C 0.81389(16) 0.53109(11) 0.34805(7) 0.0429(3) Uani 1 1 d . . . . . H10 H 0.756352 0.520923 0.302953 0.051 Uiso 1 1 calc R U . . . C11 C 0.9739(2) 0.52285(17) 0.34125(11) 0.0726(6) Uani 1 1 d . . . . . H11A H 1.033655 0.535774 0.384257 0.109 Uiso 1 1 calc R U . . . H11B H 0.996543 0.568476 0.308349 0.109 Uiso 1 1 calc R U . . . H11C H 0.993787 0.459047 0.326790 0.109 Uiso 1 1 calc R U . . . C12 C 0.7806(2) 0.62979(12) 0.37012(10) 0.0642(5) Uani 1 1 d . . . . . H12A H 0.678124 0.634182 0.373968 0.096 Uiso 1 1 calc R U . . . H12B H 0.803062 0.675587 0.337303 0.096 Uiso 1 1 calc R U . . . H12C H 0.839202 0.643230 0.413315 0.096 Uiso 1 1 calc R U . . . C13 C 0.42253(15) 0.31902(11) 0.41386(7) 0.0436(3) Uani 1 1 d . . . . . H13 H 0.366995 0.355046 0.376048 0.052 Uiso 1 1 calc R U . . . C14 C 0.42567(19) 0.21604(13) 0.39268(11) 0.0665(5) Uani 1 1 d . . . . . H14A H 0.470563 0.211205 0.352596 0.100 Uiso 1 1 calc R U . . . H14B H 0.326897 0.191630 0.383367 0.100 Uiso 1 1 calc R U . . . H14C H 0.481574 0.179177 0.428481 0.100 Uiso 1 1 calc R U . . . C15 C 0.3456(2) 0.33145(18) 0.47384(10) 0.0734(6) Uani 1 1 d . . . . . H15A H 0.397414 0.296444 0.511703 0.110 Uiso 1 1 calc R U . . . H15B H 0.246741 0.307487 0.463113 0.110 Uiso 1 1 calc R U . . . H15C H 0.343188 0.398412 0.485211 0.110 Uiso 1 1 calc R U . . . C16 C 0.34621(12) 0.51415(8) 0.16183(6) 0.0281(2) Uani 1 1 d . . . . . C17 C 0.42959(13) 0.57452(9) 0.12874(6) 0.0327(3) Uani 1 1 d . . . . . C18 C 0.39546(16) 0.58056(11) 0.05987(7) 0.0425(3) Uani 1 1 d . . . . . H18 H 0.450721 0.620216 0.036060 0.051 Uiso 1 1 calc R U . . . C19 C 0.28208(18) 0.52947(11) 0.02586(7) 0.0473(4) Uani 1 1 d . . . . . H19 H 0.261661 0.533039 -0.021221 0.057 Uiso 1 1 calc R U . . . C20 C 0.19812(16) 0.47331(11) 0.05954(7) 0.0436(3) Uani 1 1 d . . . . . H20 H 0.118717 0.440216 0.035375 0.052 Uiso 1 1 calc R U . . . C21 C 0.22788(13) 0.46430(9) 0.12850(6) 0.0333(3) Uani 1 1 d . . . . . C22 C 0.55035(14) 0.63394(10) 0.16636(7) 0.0403(3) Uani 1 1 d . . . . . H22 H 0.566496 0.612031 0.213567 0.048 Uiso 1 1 calc R U . . . C23 C 0.69190(18) 0.62255(17) 0.14009(12) 0.0756(6) Uani 1 1 d . . . . . H23A H 0.718941 0.555858 0.141165 0.113 Uiso 1 1 calc R U . . . H23B H 0.767410 0.658756 0.167889 0.113 Uiso 1 1 calc R U . . . H23C H 0.680674 0.645672 0.094278 0.113 Uiso 1 1 calc R U . . . C24 C 0.50598(19) 0.73696(12) 0.16630(10) 0.0605(5) Uani 1 1 d . . . . . H24A H 0.486519 0.760141 0.120478 0.091 Uiso 1 1 calc R U . . . H24B H 0.584083 0.773939 0.191672 0.091 Uiso 1 1 calc R U . . . H24C H 0.418772 0.743154 0.186711 0.091 Uiso 1 1 calc R U . . . C25 C 0.1423(16) 0.4026(9) 0.1634(8) 0.041(3) Uani 0.514(11) 1 d . . P A 1 H25 H 0.155363 0.424656 0.210570 0.050 Uiso 0.514(11) 1 calc R U P A 1 C26 C 0.1840(6) 0.2995(4) 0.1651(3) 0.0529(11) Uani 0.514(11) 1 d . . P A 1 H26A H 0.178107 0.275936 0.119534 0.079 Uiso 0.514(11) 1 calc R U P A 1 H26B H 0.117961 0.263509 0.188169 0.079 Uiso 0.514(11) 1 calc R U P A 1 H26C H 0.282882 0.292241 0.188560 0.079 Uiso 0.514(11) 1 calc R U P A 1 C27 C -0.0254(4) 0.4083(5) 0.1356(5) 0.077(2) Uani 0.514(11) 1 d . . P A 1 H27A H -0.055208 0.474382 0.131301 0.116 Uiso 0.514(11) 1 calc R U P A 1 H27B H -0.079476 0.376152 0.166341 0.116 Uiso 0.514(11) 1 calc R U P A 1 H27C H -0.044949 0.377733 0.091989 0.116 Uiso 0.514(11) 1 calc R U P A 1 C25A C 0.1287(17) 0.4044(8) 0.1687(9) 0.037(2) Uani 0.486(11) 1 d . . P A 2 H25A H 0.176804 0.401684 0.216041 0.044 Uiso 0.486(11) 1 calc R U P A 2 C26A C 0.1188(12) 0.3039(5) 0.1414(5) 0.082(2) Uani 0.486(11) 1 d . . P A 2 H26D H 0.070354 0.263675 0.170064 0.123 Uiso 0.486(11) 1 calc R U P A 2 H26E H 0.216061 0.279682 0.140180 0.123 Uiso 0.486(11) 1 calc R U P A 2 H26F H 0.063533 0.303887 0.096316 0.123 Uiso 0.486(11) 1 calc R U P A 2 C27A C -0.0103(5) 0.4510(6) 0.1668(3) 0.0642(16) Uani 0.486(11) 1 d . . P A 2 H27D H 0.004812 0.514110 0.186061 0.096 Uiso 0.486(11) 1 calc R U P A 2 H27E H -0.070527 0.414164 0.192336 0.096 Uiso 0.486(11) 1 calc R U P A 2 H27F H -0.058469 0.456111 0.120589 0.096 Uiso 0.486(11) 1 calc R U P A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0529(2) 0.0467(2) 0.03151(19) -0.00739(15) -0.00197(15) 0.02542(17) C1 0.0616(9) 0.0410(8) 0.0352(7) -0.0020(6) 0.0116(6) 0.0232(7) O1 0.1321(13) 0.0833(10) 0.0304(6) -0.0012(6) 0.0112(7) 0.0619(9) B1 0.0294(6) 0.0267(6) 0.0248(6) -0.0019(5) 0.0040(5) 0.0011(5) N2 0.0295(5) 0.0290(5) 0.0253(5) -0.0021(4) 0.0040(4) 0.0048(4) N1 0.0321(5) 0.0294(5) 0.0234(5) -0.0014(4) 0.0041(4) 0.0007(4) C2 0.0403(7) 0.0369(7) 0.0289(6) -0.0064(5) 0.0103(5) 0.0040(5) C3 0.0362(6) 0.0355(6) 0.0337(6) -0.0050(5) 0.0090(5) 0.0089(5) C4 0.0333(6) 0.0310(6) 0.0220(5) -0.0027(4) 0.0012(4) -0.0034(5) C5 0.0362(6) 0.0356(6) 0.0300(6) -0.0066(5) 0.0035(5) -0.0080(5) C6 0.0359(7) 0.0521(8) 0.0423(8) -0.0096(6) -0.0071(6) -0.0076(6) C7 0.0544(9) 0.0576(9) 0.0369(8) 0.0037(7) -0.0176(7) -0.0027(7) C8 0.0599(9) 0.0525(9) 0.0330(7) 0.0121(6) -0.0048(6) -0.0104(7) C9 0.0403(7) 0.0416(7) 0.0263(6) 0.0021(5) 0.0008(5) -0.0094(6) C10 0.0448(7) 0.0469(8) 0.0386(7) -0.0051(6) 0.0118(6) -0.0183(6) C11 0.0567(10) 0.0846(14) 0.0840(14) -0.0118(11) 0.0347(10) -0.0256(10) C12 0.0868(13) 0.0408(9) 0.0714(12) -0.0006(8) 0.0316(10) -0.0210(9) C13 0.0413(7) 0.0524(8) 0.0374(7) 0.0058(6) 0.0069(6) -0.0146(6) C14 0.0510(9) 0.0562(10) 0.0921(14) -0.0068(10) 0.0112(9) -0.0237(8) C15 0.0607(11) 0.1073(17) 0.0567(11) -0.0024(11) 0.0229(9) -0.0171(11) C16 0.0295(5) 0.0278(6) 0.0263(6) -0.0001(4) 0.0021(4) 0.0087(4) C17 0.0328(6) 0.0320(6) 0.0334(6) 0.0032(5) 0.0053(5) 0.0082(5) C18 0.0496(8) 0.0441(8) 0.0350(7) 0.0083(6) 0.0100(6) 0.0101(6) C19 0.0614(9) 0.0531(9) 0.0251(6) 0.0016(6) 0.0000(6) 0.0151(7) C20 0.0467(8) 0.0435(8) 0.0361(7) -0.0074(6) -0.0073(6) 0.0066(6) C21 0.0332(6) 0.0308(6) 0.0340(6) -0.0031(5) -0.0004(5) 0.0062(5) C22 0.0345(6) 0.0398(7) 0.0461(8) 0.0058(6) 0.0053(6) -0.0012(5) C23 0.0374(8) 0.0875(15) 0.1050(16) -0.0188(13) 0.0207(9) -0.0043(9) C24 0.0531(9) 0.0409(8) 0.0841(13) -0.0078(8) 0.0010(9) -0.0038(7) C25 0.027(3) 0.053(4) 0.041(4) -0.011(3) -0.003(3) 0.003(2) C26 0.059(3) 0.0385(18) 0.059(3) 0.0058(17) 0.0032(18) -0.0067(18) C27 0.0363(18) 0.068(3) 0.124(5) 0.014(3) 0.001(2) -0.0024(19) C25A 0.039(4) 0.031(3) 0.043(4) 0.000(3) 0.013(3) -0.011(3) C26A 0.107(6) 0.049(3) 0.099(5) -0.020(3) 0.047(4) -0.027(4) C27A 0.045(2) 0.086(4) 0.065(3) 0.006(2) 0.0151(19) 0.004(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' O O 0.0492 0.0322 '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 98.92(6) O1 C1 P1 170.91(13) N1 B1 N2 105.64(10) N1 B1 P1 120.37(9) N2 B1 P1 133.98(9) C3 N2 B1 107.84(10) C3 N2 C16 124.01(10) B1 N2 C16 127.29(10) C2 N1 B1 108.01(10) C2 N1 C4 123.41(10) B1 N1 C4 128.58(10) C3 C2 N1 109.22(11) C3 C2 H2 125.4 N1 C2 H2 125.4 C2 C3 N2 109.29(11) C2 C3 H3 125.4 N2 C3 H3 125.4 C9 C4 C5 121.99(11) C9 C4 N1 118.88(11) C5 C4 N1 119.10(11) C6 C5 C4 117.50(12) C6 C5 C10 121.63(12) C4 C5 C10 120.87(12) C7 C6 C5 121.30(13) C7 C6 H6 119.4 C5 C6 H6 119.4 C8 C7 C6 120.11(13) C8 C7 H7 119.9 C6 C7 H7 119.9 C7 C8 C9 121.18(14) C7 C8 H8 119.4 C9 C8 H8 119.4 C8 C9 C4 117.87(12) C8 C9 C13 119.98(13) C4 C9 C13 122.07(12) C5 C10 C12 110.73(12) C5 C10 C11 113.33(15) C12 C10 C11 110.33(14) C5 C10 H10 107.4 C12 C10 H10 107.4 C11 C10 H10 107.4 C10 C11 H11A 109.5 C10 C11 H11B 109.5 H11A C11 H11B 109.5 C10 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 C10 C12 H12A 109.5 C10 C12 H12B 109.5 H12A C12 H12B 109.5 C10 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C9 C13 C15 111.97(13) C9 C13 C14 109.96(13) C15 C13 C14 111.74(15) C9 C13 H13 107.7 C15 C13 H13 107.7 C14 C13 H13 107.7 C13 C14 H14A 109.5 C13 C14 H14B 109.5 H14A C14 H14B 109.5 C13 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C13 C15 H15A 109.5 C13 C15 H15B 109.5 H15A C15 H15B 109.5 C13 C15 H15C 109.5 H15A C15 H15C 109.5 H15B C15 H15C 109.5 C21 C16 C17 122.43(11) C21 C16 N2 119.32(11) C17 C16 N2 118.18(11) C18 C17 C16 117.77(12) C18 C17 C22 120.53(12) C16 C17 C22 121.67(11) C19 C18 C17 120.61(14) C19 C18 H18 119.7 C17 C18 H18 119.7 C20 C19 C18 120.69(13) C20 C19 H19 119.7 C18 C19 H19 119.7 C19 C20 C21 121.09(13) C19 C20 H20 119.5 C21 C20 H20 119.5 C20 C21 C16 117.33(13) C20 C21 C25 120.8(6) C16 C21 C25 121.8(5) C20 C21 C25A 122.1(6) C16 C21 C25A 120.5(6) C23 C22 C17 112.79(14) C23 C22 C24 110.92(15) C17 C22 C24 110.59(12) C23 C22 H22 107.4 C17 C22 H22 107.4 C24 C22 H22 107.4 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 C21 C25 C26 115.7(12) C21 C25 C27 112.9(8) C26 C25 C27 107.1(8) C21 C25 H25 106.9 C26 C25 H25 106.9 C27 C25 H25 106.9 C25 C26 H26A 109.5 C25 C26 H26B 109.5 H26A C26 H26B 109.5 C25 C26 H26C 109.5 H26A C26 H26C 109.5 H26B C26 H26C 109.5 C25 C27 H27A 109.5 C25 C27 H27B 109.5 H27A C27 H27B 109.5 C25 C27 H27C 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 C27A C25A C26A 114.3(9) C27A C25A C21 109.9(8) C26A C25A C21 108.7(12) C27A C25A H25A 107.9 C26A C25A H25A 107.9 C21 C25A H25A 107.9 C25A C26A H26D 109.5 C25A C26A H26E 109.5 H26D C26A H26E 109.5 C25A C26A H26F 109.5 H26D C26A H26F 109.5 H26E C26A H26F 109.5 C25A C27A H27D 109.5 C25A C27A H27E 109.5 H27D C27A H27E 109.5 C25A C27A H27F 109.5 H27D C27A H27F 109.5 H27E C27A H27F 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 C1 1.6523(15) P1 B1 1.9126(14) C1 O1 1.1526(18) B1 N1 1.4218(16) B1 N2 1.4224(16) N2 C3 1.4008(15) N2 C16 1.4314(14) N1 C2 1.3985(16) N1 C4 1.4347(15) C2 C3 1.3431(18) C2 H2 0.9500 C3 H3 0.9500 C4 C9 1.3957(17) C4 C5 1.4091(17) C5 C6 1.3906(19) C5 C10 1.5184(19) C6 C7 1.380(2) C6 H6 0.9500 C7 C8 1.378(2) C7 H7 0.9500 C8 C9 1.3927(19) C8 H8 0.9500 C9 C13 1.5194(18) C10 C12 1.520(2) C10 C11 1.536(2) C10 H10 1.0000 C11 H11A 0.9800 C11 H11B 0.9800 C11 H11C 0.9800 C12 H12A 0.9800 C12 H12B 0.9800 C12 H12C 0.9800 C13 C15 1.527(2) C13 C14 1.527(2) C13 H13 1.0000 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 H15A 0.9800 C15 H15B 0.9800 C15 H15C 0.9800 C16 C21 1.3990(17) C16 C17 1.4042(17) C17 C18 1.3925(18) C17 C22 1.5195(19) C18 C19 1.380(2) C18 H18 0.9500 C19 C20 1.379(2) C19 H19 0.9500 C20 C21 1.3952(18) C20 H20 0.9500 C21 C25 1.450(15) C21 C25A 1.583(16) C22 C23 1.519(2) C22 C24 1.521(2) 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 C25 C26 1.515(15) C25 C27 1.588(15) C25 H25 1.0000 C26 H26A 0.9800 C26 H26B 0.9800 C26 H26C 0.9800 C27 H27A 0.9800 C27 H27B 0.9800 C27 H27C 0.9800 C25A C27A 1.458(18) C25A C26A 1.530(14) C25A H25A 1.0000 C26A H26D 0.9800 C26A H26E 0.9800 C26A H26F 0.9800 C27A H27D 0.9800 C27A H27E 0.9800 C27A H27F 0.9800