#------------------------------------------------------------------------------ #$Date: 2020-02-04 22:09:40 +0200 (Tue, 04 Feb 2020) $ #$Revision: 247617 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125676.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_7125676 loop_ _publ_author_name 'Livshits-Kritsman, Yulia' 'Tumanskii, Boris' 'M\'enard, Gabriel' 'Dobrovetsky, Roman' _publ_section_title ; Isolable cyclic (alkyl)(amino)carbene-phosphonyl radical adducts. ; _journal_issue 9 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 1341 _journal_page_last 1344 _journal_paper_doi 10.1039/c9cc09244g _journal_volume 56 _journal_year 2020 _chemical_formula_moiety 'C32 H41 N O P' _chemical_formula_sum 'C32 H41 N O P' _chemical_formula_weight 486.63 _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 _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/1 _audit_update_record ; 2019-11-21 deposited with the CCDC. 2019-12-20 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.5850(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.5072(3) _cell_length_b 14.0611(3) _cell_length_c 18.7738(5) _cell_measurement_reflns_used 30026 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 28.391 _cell_measurement_theta_min 1.828 _cell_volume 2696.09(12) _computing_cell_refinement 'Saint, Bruker-AXS' _computing_data_collection 'Apex2, Bruker-AXS' _computing_data_reduction 'Saint, Bruker-AXS' _computing_structure_refinement 'SHELXL-2018/1 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 110(2) _diffrn_detector_area_resol_mean 1.75 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'ApexDuo, Bruker-AXS' _diffrn_measurement_method '0.5 deg. \f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_unetI/netI 0.0361 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 30026 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.391 _diffrn_reflns_theta_min 1.828 _diffrn_source 'ImuS micro-focus' _exptl_absorpt_coefficient_mu 0.125 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_correction_T_min 0.971 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs, Bruker-AXS' _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.199 _exptl_crystal_description prism _exptl_crystal_F_000 1052 _exptl_crystal_size_max 0.232 _exptl_crystal_size_mid 0.193 _exptl_crystal_size_min 0.164 _refine_diff_density_max 0.776 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.052 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 324 _refine_ls_number_reflns 6723 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0539 _refine_ls_R_factor_gt 0.0415 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0498P)^2^+1.3710P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1056 _refine_ls_wR_factor_ref 0.1129 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5482 _reflns_number_total 6723 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc09244g2.cif _cod_data_source_block rom92 _cod_depositor_comments 'Adding full bibliography for 7125674--7125677.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7125676 _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 0.971 _shelx_estimated_absorpt_t_max 0.980 _shelx_res_file ; TITL mo_rom92_0m_a.res in P2(1)/n rom92.res created by SHELXL-2018/1 at 13:45:53 on 11-Nov-2019 REM Old TITL mo_rom92_0m in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.123, Rweak 0.004, Alpha 0.028, Orientation as input REM Formula found by SHELXT: C32 N O P CELL 0.71073 10.5072 14.0611 18.7738 90.000 103.585 90.000 ZERR 4.000 0.0003 0.0003 0.0005 0.000 0.001 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O P DISP $C 0.00341 0.00169 11.32113!source kissel DISP $H -0.00002 0.00000 0.66638!source kissel DISP $N 0.00664 0.00342 19.38436!source kissel DISP $O 0.01140 0.00623 32.03669!source kissel DISP $P 0.10406 0.09609 404.11213!source kissel UNIT 128 164 4 4 4 TEMP -163.000 SIZE 0.164 0.193 0.232 ACTA L.S. 10 BOND $H LIST 6 FMAP 2 PLAN 20 WGHT 0.049800 1.371000 FVAR 0.37675 P1 5 0.512401 0.801614 0.728814 11.00000 0.01229 0.01179 = 0.01176 -0.00026 0.00242 -0.00011 O2 4 0.528168 0.906242 0.738056 11.00000 0.02168 0.01448 = 0.02376 -0.00339 0.00689 -0.00300 C3 1 0.458460 0.757928 0.633892 11.00000 0.01015 0.01989 = 0.01130 -0.00012 0.00255 -0.00092 C4 1 0.554052 0.781860 0.582836 11.00000 0.01181 0.01732 = 0.01352 0.00257 0.00453 -0.00028 C5 1 0.636167 0.694540 0.572870 11.00000 0.01777 0.02360 = 0.02042 0.00272 0.00796 0.00332 AFIX 137 H5A 2 0.578206 0.639949 0.557582 11.00000 -1.50000 H5B 2 0.698078 0.679918 0.619357 11.00000 -1.50000 H5C 2 0.684571 0.708084 0.535317 11.00000 -1.50000 AFIX 0 C6 1 0.650126 0.864505 0.607623 11.00000 0.01434 0.02477 = 0.01649 0.00371 0.00399 -0.00426 AFIX 137 H6A 2 0.700270 0.875950 0.570542 11.00000 -1.50000 H6B 2 0.710220 0.848215 0.654346 11.00000 -1.50000 H6C 2 0.601108 0.922011 0.613774 11.00000 -1.50000 AFIX 0 C7 1 0.457547 0.807463 0.509948 11.00000 0.01570 0.01755 = 0.01249 0.00204 0.00438 -0.00129 AFIX 23 H7A 2 0.495262 0.857721 0.484200 11.00000 -1.20000 H7AB 2 0.439619 0.750858 0.477788 11.00000 -1.20000 AFIX 0 C8 1 0.330501 0.842887 0.528001 11.00000 0.01372 0.01607 = 0.01258 0.00371 0.00351 -0.00004 C9 1 0.336355 0.950169 0.544415 11.00000 0.02192 0.01725 = 0.02337 0.00582 0.00925 0.00135 AFIX 137 H9A 2 0.362722 0.984322 0.504698 11.00000 -1.50000 H9B 2 0.400239 0.962164 0.590712 11.00000 -1.50000 H9C 2 0.249834 0.972380 0.548294 11.00000 -1.50000 AFIX 0 C10 1 0.212120 0.822056 0.465305 11.00000 0.01523 0.02908 = 0.01371 0.00476 0.00164 0.00092 AFIX 137 H10A 2 0.218825 0.858929 0.422041 11.00000 -1.50000 H10B 2 0.131804 0.839804 0.480028 11.00000 -1.50000 H10C 2 0.209737 0.754062 0.453601 11.00000 -1.50000 AFIX 0 N11 3 0.327869 0.787966 0.595723 11.00000 0.00949 0.01295 = 0.01174 0.00329 0.00167 -0.00160 C12 1 0.217500 0.731629 0.603116 11.00000 0.01108 0.01501 = 0.01158 0.00098 0.00128 -0.00278 C13 1 0.121073 0.773494 0.633947 11.00000 0.01296 0.01666 = 0.01189 -0.00017 0.00139 -0.00074 C14 1 0.020556 0.716625 0.647837 11.00000 0.01489 0.02494 = 0.02218 -0.00366 0.00851 -0.00373 AFIX 43 H14 2 -0.045513 0.744757 0.667871 11.00000 -1.20000 AFIX 0 C15 1 0.015381 0.620240 0.632998 11.00000 0.02127 0.02484 = 0.02860 -0.00419 0.01117 -0.01154 AFIX 43 H15 2 -0.050583 0.581813 0.645408 11.00000 -1.20000 AFIX 0 C16 1 0.107321 0.580186 0.599846 11.00000 0.02365 0.01727 = 0.02496 -0.00486 0.00814 -0.00874 AFIX 43 H16 2 0.101903 0.514309 0.588295 11.00000 -1.20000 AFIX 0 C17 1 0.207340 0.634136 0.583082 11.00000 0.01510 0.01563 = 0.01518 -0.00159 0.00260 -0.00251 C18 1 0.123134 0.878532 0.653873 11.00000 0.01288 0.01592 = 0.01904 -0.00052 0.00620 0.00043 AFIX 13 H18 2 0.210365 0.904913 0.651381 11.00000 -1.20000 AFIX 0 C19 1 0.017202 0.933697 0.598973 11.00000 0.01868 0.02366 = 0.02689 0.00418 0.00492 0.00373 AFIX 137 H19A 2 0.028616 0.923441 0.549216 11.00000 -1.50000 H19B 2 0.025020 1.001704 0.610603 11.00000 -1.50000 H19C 2 -0.069549 0.911109 0.602107 11.00000 -1.50000 AFIX 0 C20 1 0.104936 0.895133 0.731440 11.00000 0.02381 0.01966 = 0.02102 -0.00214 0.00905 0.00295 AFIX 137 H20A 2 0.123239 0.961896 0.745044 11.00000 -1.50000 H20B 2 0.165314 0.854202 0.765952 11.00000 -1.50000 H20C 2 0.014604 0.879931 0.732992 11.00000 -1.50000 AFIX 0 C21 1 0.299599 0.585338 0.542910 11.00000 0.01689 0.01439 = 0.01740 -0.00271 0.00408 -0.00220 AFIX 13 H21 2 0.362308 0.634207 0.532884 11.00000 -1.20000 AFIX 0 C22 1 0.224330 0.544680 0.468977 11.00000 0.02436 0.02331 = 0.02219 -0.00814 0.00230 -0.00053 AFIX 137 H22A 2 0.171012 0.594938 0.440366 11.00000 -1.50000 H22B 2 0.167344 0.492853 0.477519 11.00000 -1.50000 H22C 2 0.286648 0.520330 0.441915 11.00000 -1.50000 AFIX 0 C23 1 0.379662 0.505370 0.588102 11.00000 0.02513 0.01756 = 0.02266 -0.00066 0.00516 0.00006 AFIX 137 H23A 2 0.320292 0.456010 0.598045 11.00000 -1.50000 H23B 2 0.430646 0.531289 0.634538 11.00000 -1.50000 H23C 2 0.439157 0.477761 0.560573 11.00000 -1.50000 AFIX 0 C24 1 0.408692 0.754612 0.785525 11.00000 0.01318 0.01624 = 0.01333 0.00219 0.00298 0.00407 C25 1 0.415106 0.804919 0.850528 11.00000 0.01789 0.02184 = 0.01677 -0.00153 0.00390 0.00281 AFIX 43 H25 2 0.463493 0.862532 0.859285 11.00000 -1.20000 AFIX 0 C26 1 0.351206 0.771232 0.902398 11.00000 0.02810 0.03103 = 0.01581 -0.00169 0.00848 0.00739 AFIX 43 H26 2 0.357876 0.804841 0.947022 11.00000 -1.20000 AFIX 0 C27 1 0.277781 0.688590 0.888947 11.00000 0.02756 0.02970 = 0.02291 0.00878 0.01469 0.00726 AFIX 43 H27 2 0.232938 0.666140 0.924074 11.00000 -1.20000 AFIX 0 C28 1 0.269469 0.638478 0.824390 11.00000 0.02174 0.01954 = 0.02679 0.00643 0.01004 0.00214 AFIX 43 H28 2 0.218746 0.581940 0.815269 11.00000 -1.20000 AFIX 0 C29 1 0.335440 0.671038 0.772990 11.00000 0.01764 0.01728 = 0.01603 0.00183 0.00461 0.00250 AFIX 43 H29 2 0.330546 0.636128 0.729105 11.00000 -1.20000 AFIX 0 C30 1 0.664037 0.736802 0.763467 11.00000 0.01423 0.02367 = 0.01076 0.00296 0.00342 0.00325 C31 1 0.778179 0.786572 0.794601 11.00000 0.01827 0.03488 = 0.01456 0.00808 0.00337 -0.00409 AFIX 43 H31 2 0.775596 0.853686 0.799908 11.00000 -1.20000 AFIX 0 C32 1 0.896397 0.737800 0.818007 11.00000 0.01340 0.06497 = 0.02020 0.01967 0.00202 -0.00210 AFIX 43 H32 2 0.974078 0.771770 0.839505 11.00000 -1.20000 AFIX 0 C33 1 0.900668 0.640323 0.809984 11.00000 0.02311 0.06369 = 0.02316 0.02156 0.01163 0.02296 AFIX 43 H33 2 0.981737 0.607675 0.824843 11.00000 -1.20000 AFIX 0 C34 1 0.787801 0.590111 0.780500 11.00000 0.03917 0.03828 = 0.01730 0.00635 0.00777 0.02364 AFIX 43 H34 2 0.791067 0.523000 0.775371 11.00000 -1.20000 AFIX 0 C35 1 0.669490 0.637817 0.758347 11.00000 0.02599 0.02527 = 0.01558 0.00113 0.00101 0.00837 AFIX 43 H35 2 0.591471 0.602853 0.739525 11.00000 -1.20000 AFIX 0 HKLF 4 REM mo_rom92_0m_a.res in P2(1)/n REM R1 = 0.0415 for 5482 Fo > 4sig(Fo) and 0.0539 for all 6723 data REM 324 parameters refined using 0 restraints END WGHT 0.0498 1.3733 REM Highest difference peak 0.776, deepest hole -0.413, 1-sigma level 0.052 Q1 1 0.4604 0.6855 0.6410 11.00000 0.05 0.78 Q2 1 0.4764 0.7756 0.6778 11.00000 0.05 0.47 Q3 1 0.4564 0.7738 0.7608 11.00000 0.05 0.40 Q4 1 0.5138 0.7961 0.5481 11.00000 0.05 0.37 Q5 1 0.5974 0.7682 0.7451 11.00000 0.05 0.35 Q6 1 0.5047 0.7667 0.6098 11.00000 0.05 0.34 Q7 1 0.2583 0.6097 0.5661 11.00000 0.05 0.32 Q8 1 0.2789 0.8321 0.4979 11.00000 0.05 0.32 Q9 1 0.2240 0.6786 0.5989 11.00000 0.05 0.30 Q10 1 0.7234 0.7569 0.7857 11.00000 0.05 0.30 Q11 1 0.3988 0.8296 0.5194 11.00000 0.05 0.29 Q12 1 0.3334 0.8950 0.5368 11.00000 0.05 0.28 Q13 1 0.1166 0.8216 0.6417 11.00000 0.05 0.28 Q14 1 0.3993 0.7688 0.6178 11.00000 0.05 0.27 Q15 1 0.5934 0.8226 0.5955 11.00000 0.05 0.26 Q16 1 0.1740 0.7469 0.6296 11.00000 0.05 0.26 Q17 1 0.2700 0.7601 0.6010 11.00000 0.05 0.26 Q18 1 0.2638 0.5620 0.5063 11.00000 0.05 0.25 Q19 1 0.3878 0.7863 0.8081 11.00000 0.05 0.24 Q20 1 0.3785 0.7828 0.8746 11.00000 0.05 0.24 ; _shelx_res_checksum 39557 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 P1 P 0.51240(3) 0.80161(2) 0.72881(2) 0.01202(9) Uani 1 1 d . . O2 O 0.52817(10) 0.90624(7) 0.73806(6) 0.0197(2) Uani 1 1 d . . C3 C 0.45846(13) 0.75793(10) 0.63389(7) 0.0138(3) Uani 1 1 d . . C4 C 0.55405(13) 0.78186(10) 0.58284(7) 0.0140(3) Uani 1 1 d . . C5 C 0.63617(15) 0.69454(11) 0.57287(8) 0.0200(3) Uani 1 1 d . . H5A H 0.578206 0.639949 0.557582 0.030 Uiso 1 1 calc R U H5B H 0.698078 0.679918 0.619357 0.030 Uiso 1 1 calc R U H5C H 0.684571 0.708084 0.535317 0.030 Uiso 1 1 calc R U C6 C 0.65013(14) 0.86450(11) 0.60762(8) 0.0185(3) Uani 1 1 d . . H6A H 0.700270 0.875950 0.570542 0.028 Uiso 1 1 calc R U H6B H 0.710220 0.848215 0.654346 0.028 Uiso 1 1 calc R U H6C H 0.601108 0.922011 0.613774 0.028 Uiso 1 1 calc R U C7 C 0.45755(14) 0.80746(10) 0.50995(7) 0.0151(3) Uani 1 1 d . . H7A H 0.495262 0.857721 0.484200 0.018 Uiso 1 1 calc R U H7AB H 0.439619 0.750858 0.477788 0.018 Uiso 1 1 calc R U C8 C 0.33050(13) 0.84289(10) 0.52800(7) 0.0141(3) Uani 1 1 d . . C9 C 0.33635(15) 0.95017(10) 0.54442(8) 0.0202(3) Uani 1 1 d . . H9A H 0.362722 0.984322 0.504698 0.030 Uiso 1 1 calc R U H9B H 0.400239 0.962164 0.590712 0.030 Uiso 1 1 calc R U H9C H 0.249834 0.972380 0.548294 0.030 Uiso 1 1 calc R U C10 C 0.21212(14) 0.82206(11) 0.46531(8) 0.0196(3) Uani 1 1 d . . H10A H 0.218825 0.858929 0.422041 0.029 Uiso 1 1 calc R U H10B H 0.131804 0.839804 0.480028 0.029 Uiso 1 1 calc R U H10C H 0.209737 0.754062 0.453601 0.029 Uiso 1 1 calc R U N11 N 0.32787(11) 0.78797(8) 0.59572(6) 0.0115(2) Uani 1 1 d . . C12 C 0.21750(13) 0.73163(9) 0.60312(7) 0.0128(3) Uani 1 1 d . . C13 C 0.12107(13) 0.77349(10) 0.63395(7) 0.0141(3) Uani 1 1 d . . C14 C 0.02056(15) 0.71663(11) 0.64784(8) 0.0200(3) Uani 1 1 d . . H14 H -0.045513 0.744757 0.667871 0.024 Uiso 1 1 calc R U C15 C 0.01538(16) 0.62024(11) 0.63300(9) 0.0240(3) Uani 1 1 d . . H15 H -0.050583 0.581813 0.645408 0.029 Uiso 1 1 calc R U C16 C 0.10732(15) 0.58019(11) 0.59985(8) 0.0216(3) Uani 1 1 d . . H16 H 0.101903 0.514309 0.588295 0.026 Uiso 1 1 calc R U C17 C 0.20734(14) 0.63414(10) 0.58308(7) 0.0155(3) Uani 1 1 d . . C18 C 0.12313(14) 0.87853(10) 0.65387(7) 0.0155(3) Uani 1 1 d . . H18 H 0.210365 0.904913 0.651381 0.019 Uiso 1 1 calc R U C19 C 0.01720(15) 0.93370(11) 0.59897(9) 0.0231(3) Uani 1 1 d . . H19A H 0.028616 0.923441 0.549216 0.035 Uiso 1 1 calc R U H19B H 0.025020 1.001704 0.610603 0.035 Uiso 1 1 calc R U H19C H -0.069549 0.911109 0.602107 0.035 Uiso 1 1 calc R U C20 C 0.10494(16) 0.89513(11) 0.73144(8) 0.0209(3) Uani 1 1 d . . H20A H 0.123239 0.961896 0.745044 0.031 Uiso 1 1 calc R U H20B H 0.165314 0.854202 0.765952 0.031 Uiso 1 1 calc R U H20C H 0.014604 0.879931 0.732992 0.031 Uiso 1 1 calc R U C21 C 0.29960(14) 0.58534(10) 0.54291(7) 0.0162(3) Uani 1 1 d . . H21 H 0.362308 0.634207 0.532884 0.019 Uiso 1 1 calc R U C22 C 0.22433(16) 0.54468(11) 0.46898(8) 0.0238(3) Uani 1 1 d . . H22A H 0.171012 0.594938 0.440366 0.036 Uiso 1 1 calc R U H22B H 0.167344 0.492853 0.477519 0.036 Uiso 1 1 calc R U H22C H 0.286648 0.520330 0.441915 0.036 Uiso 1 1 calc R U C23 C 0.37966(16) 0.50537(11) 0.58810(8) 0.0219(3) Uani 1 1 d . . H23A H 0.320292 0.456010 0.598045 0.033 Uiso 1 1 calc R U H23B H 0.430646 0.531289 0.634538 0.033 Uiso 1 1 calc R U H23C H 0.439157 0.477761 0.560573 0.033 Uiso 1 1 calc R U C24 C 0.40869(13) 0.75461(10) 0.78553(7) 0.0143(3) Uani 1 1 d . . C25 C 0.41511(15) 0.80492(11) 0.85053(8) 0.0189(3) Uani 1 1 d . . H25 H 0.463493 0.862532 0.859285 0.023 Uiso 1 1 calc R U C26 C 0.35121(16) 0.77123(12) 0.90240(8) 0.0244(3) Uani 1 1 d . . H26 H 0.357876 0.804841 0.947022 0.029 Uiso 1 1 calc R U C27 C 0.27778(17) 0.68859(12) 0.88895(9) 0.0253(3) Uani 1 1 d . . H27 H 0.232938 0.666140 0.924074 0.030 Uiso 1 1 calc R U C28 C 0.26947(15) 0.63848(11) 0.82439(8) 0.0220(3) Uani 1 1 d . . H28 H 0.218746 0.581940 0.815269 0.026 Uiso 1 1 calc R U C29 C 0.33544(14) 0.67104(10) 0.77299(8) 0.0169(3) Uani 1 1 d . . H29 H 0.330546 0.636128 0.729105 0.020 Uiso 1 1 calc R U C30 C 0.66404(14) 0.73680(10) 0.76347(7) 0.0161(3) Uani 1 1 d . . C31 C 0.77818(15) 0.78657(12) 0.79460(8) 0.0227(3) Uani 1 1 d . . H31 H 0.775596 0.853686 0.799908 0.027 Uiso 1 1 calc R U C32 C 0.89640(16) 0.73780(15) 0.81801(9) 0.0332(4) Uani 1 1 d . . H32 H 0.974078 0.771770 0.839505 0.040 Uiso 1 1 calc R U C33 C 0.90067(17) 0.64032(15) 0.80998(9) 0.0356(5) Uani 1 1 d . . H33 H 0.981737 0.607675 0.824843 0.043 Uiso 1 1 calc R U C34 C 0.78780(18) 0.59011(13) 0.78050(8) 0.0314(4) Uani 1 1 d . . H34 H 0.791067 0.523000 0.775371 0.038 Uiso 1 1 calc R U C35 C 0.66949(16) 0.63782(11) 0.75835(8) 0.0229(3) Uani 1 1 d . . H35 H 0.591471 0.602853 0.739525 0.028 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 0.01229(18) 0.01179(17) 0.01176(16) -0.00026(12) 0.00242(13) -0.00011(13) O2 0.0217(6) 0.0145(5) 0.0238(5) -0.0034(4) 0.0069(4) -0.0030(4) C3 0.0102(6) 0.0199(7) 0.0113(6) -0.0001(5) 0.0026(5) -0.0009(5) C4 0.0118(6) 0.0173(7) 0.0135(6) 0.0026(5) 0.0045(5) -0.0003(5) C5 0.0178(7) 0.0236(8) 0.0204(7) 0.0027(6) 0.0080(6) 0.0033(6) C6 0.0143(7) 0.0248(8) 0.0165(7) 0.0037(6) 0.0040(5) -0.0043(6) C7 0.0157(7) 0.0175(7) 0.0125(6) 0.0020(5) 0.0044(5) -0.0013(5) C8 0.0137(7) 0.0161(7) 0.0126(6) 0.0037(5) 0.0035(5) 0.0000(5) C9 0.0219(8) 0.0173(7) 0.0234(7) 0.0058(6) 0.0092(6) 0.0013(6) C10 0.0152(7) 0.0291(8) 0.0137(6) 0.0048(6) 0.0016(5) 0.0009(6) N11 0.0095(5) 0.0129(5) 0.0117(5) 0.0033(4) 0.0017(4) -0.0016(4) C12 0.0111(6) 0.0150(6) 0.0116(6) 0.0010(5) 0.0013(5) -0.0028(5) C13 0.0130(7) 0.0167(7) 0.0119(6) -0.0002(5) 0.0014(5) -0.0007(5) C14 0.0149(7) 0.0249(8) 0.0222(7) -0.0037(6) 0.0085(6) -0.0037(6) C15 0.0213(8) 0.0248(8) 0.0286(8) -0.0042(6) 0.0112(6) -0.0115(6) C16 0.0236(8) 0.0173(7) 0.0250(7) -0.0049(6) 0.0081(6) -0.0087(6) C17 0.0151(7) 0.0156(7) 0.0152(6) -0.0016(5) 0.0026(5) -0.0025(5) C18 0.0129(7) 0.0159(7) 0.0190(7) -0.0005(5) 0.0062(5) 0.0004(5) C19 0.0187(8) 0.0237(8) 0.0269(8) 0.0042(6) 0.0049(6) 0.0037(6) C20 0.0238(8) 0.0197(7) 0.0210(7) -0.0021(6) 0.0091(6) 0.0029(6) C21 0.0169(7) 0.0144(7) 0.0174(6) -0.0027(5) 0.0041(5) -0.0022(5) C22 0.0244(8) 0.0233(8) 0.0222(7) -0.0081(6) 0.0023(6) -0.0005(6) C23 0.0251(8) 0.0176(7) 0.0227(7) -0.0007(6) 0.0052(6) 0.0001(6) C24 0.0132(7) 0.0162(7) 0.0133(6) 0.0022(5) 0.0030(5) 0.0041(5) C25 0.0179(7) 0.0218(7) 0.0168(7) -0.0015(5) 0.0039(6) 0.0028(6) C26 0.0281(9) 0.0310(8) 0.0158(7) -0.0017(6) 0.0085(6) 0.0074(7) C27 0.0276(9) 0.0297(8) 0.0229(8) 0.0088(6) 0.0147(7) 0.0073(7) C28 0.0217(8) 0.0195(7) 0.0268(8) 0.0064(6) 0.0100(6) 0.0021(6) C29 0.0176(7) 0.0173(7) 0.0160(6) 0.0018(5) 0.0046(5) 0.0025(6) C30 0.0142(7) 0.0237(7) 0.0108(6) 0.0030(5) 0.0034(5) 0.0032(6) C31 0.0183(7) 0.0349(9) 0.0146(7) 0.0081(6) 0.0034(6) -0.0041(6) C32 0.0134(7) 0.0650(13) 0.0202(8) 0.0197(8) 0.0020(6) -0.0021(8) C33 0.0231(9) 0.0637(13) 0.0232(8) 0.0216(8) 0.0116(7) 0.0230(9) C34 0.0392(10) 0.0383(10) 0.0173(7) 0.0063(7) 0.0078(7) 0.0236(8) C35 0.0260(8) 0.0253(8) 0.0156(7) 0.0011(6) 0.0010(6) 0.0084(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0034 0.0017 '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' N N 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1041 0.0961 '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 O2 P1 C24 110.94(6) O2 P1 C30 112.96(7) C24 P1 C30 101.76(6) O2 P1 C3 116.31(6) C24 P1 C3 110.77(6) C30 P1 C3 102.91(6) N11 C3 C4 107.47(10) N11 C3 P1 114.83(9) C4 C3 P1 114.88(9) C5 C4 C6 107.04(12) C5 C4 C7 110.45(11) C6 C4 C7 109.88(11) C5 C4 C3 111.03(11) C6 C4 C3 116.31(11) C7 C4 C3 102.06(11) 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 C4 C6 H6A 109.5 C4 C6 H6B 109.5 H6A C6 H6B 109.5 C4 C6 H6C 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 C8 C7 C4 107.72(11) C8 C7 H7A 110.2 C4 C7 H7A 110.2 C8 C7 H7AB 110.2 C4 C7 H7AB 110.2 H7A C7 H7AB 108.5 N11 C8 C10 112.49(11) N11 C8 C7 102.19(10) C10 C8 C7 111.15(11) N11 C8 C9 110.15(11) C10 C8 C9 109.25(12) C7 C8 C9 111.50(11) C8 C9 H9A 109.5 C8 C9 H9B 109.5 H9A C9 H9B 109.5 C8 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C8 C10 H10A 109.5 C8 C10 H10B 109.5 H10A C10 H10B 109.5 C8 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C12 N11 C3 118.80(11) C12 N11 C8 122.94(11) C3 N11 C8 111.46(10) C13 C12 C17 119.75(12) C13 C12 N11 118.93(12) C17 C12 N11 121.26(12) C14 C13 C12 119.06(13) C14 C13 C18 118.49(12) C12 C13 C18 122.44(12) C15 C14 C13 121.28(14) C15 C14 H14 119.4 C13 C14 H14 119.4 C14 C15 C16 119.37(14) C14 C15 H15 120.3 C16 C15 H15 120.3 C15 C16 C17 121.57(14) C15 C16 H16 119.2 C17 C16 H16 119.2 C16 C17 C12 118.74(13) C16 C17 C21 117.95(12) C12 C17 C21 123.31(12) C13 C18 C20 112.58(11) C13 C18 C19 111.00(12) C20 C18 C19 109.17(12) C13 C18 H18 108.0 C20 C18 H18 108.0 C19 C18 H18 108.0 C18 C19 H19A 109.5 C18 C19 H19B 109.5 H19A C19 H19B 109.5 C18 C19 H19C 109.5 H19A C19 H19C 109.5 H19B C19 H19C 109.5 C18 C20 H20A 109.5 C18 C20 H20B 109.5 H20A C20 H20B 109.5 C18 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 C17 C21 C23 112.70(12) C17 C21 C22 111.23(12) C23 C21 C22 109.00(12) C17 C21 H21 107.9 C23 C21 H21 107.9 C22 C21 H21 107.9 C21 C22 H22A 109.5 C21 C22 H22B 109.5 H22A C22 H22B 109.5 C21 C22 H22C 109.5 H22A C22 H22C 109.5 H22B C22 H22C 109.5 C21 C23 H23A 109.5 C21 C23 H23B 109.5 H23A C23 H23B 109.5 C21 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 C29 C24 C25 119.03(13) C29 C24 P1 126.22(10) C25 C24 P1 114.50(11) C26 C25 C24 120.46(14) C26 C25 H25 119.8 C24 C25 H25 119.8 C27 C26 C25 119.90(14) C27 C26 H26 120.1 C25 C26 H26 120.1 C26 C27 C28 120.25(14) C26 C27 H27 119.9 C28 C27 H27 119.9 C27 C28 C29 119.97(15) C27 C28 H28 120.0 C29 C28 H28 120.0 C28 C29 C24 120.37(13) C28 C29 H29 119.8 C24 C29 H29 119.8 C31 C30 C35 118.96(14) C31 C30 P1 119.61(12) C35 C30 P1 121.42(11) C30 C31 C32 119.99(16) C30 C31 H31 120.0 C32 C31 H31 120.0 C33 C32 C31 120.16(16) C33 C32 H32 119.9 C31 C32 H32 119.9 C34 C33 C32 120.33(15) C34 C33 H33 119.8 C32 C33 H33 119.8 C33 C34 C35 119.87(17) C33 C34 H34 120.1 C35 C34 H34 120.1 C34 C35 C30 120.61(16) C34 C35 H35 119.7 C30 C35 H35 119.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 O2 1.4861(10) P1 C24 1.8174(14) P1 C30 1.8181(14) P1 C3 1.8439(13) C3 N11 1.4535(17) C3 C4 1.5790(18) C4 C5 1.537(2) C4 C6 1.538(2) C4 C7 1.5422(19) 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 C8 1.5354(19) C7 H7A 0.9900 C7 H7AB 0.9900 C8 N11 1.4934(16) C8 C10 1.5266(19) C8 C9 1.5380(19) C9 H9A 0.9800 C9 H9B 0.9800 C9 H9C 0.9800 C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 N11 C12 1.4378(17) C12 C13 1.4084(19) C12 C17 1.4189(19) C13 C14 1.397(2) C13 C18 1.5225(19) C14 C15 1.382(2) C14 H14 0.9500 C15 C16 1.386(2) C15 H15 0.9500 C16 C17 1.391(2) C16 H16 0.9500 C17 C21 1.5241(19) C18 C20 1.5305(19) C18 C19 1.538(2) C18 H18 1.0000 C19 H19A 0.9800 C19 H19B 0.9800 C19 H19C 0.9800 C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 C21 C23 1.535(2) C21 C22 1.537(2) C21 H21 1.0000 C22 H22A 0.9800 C22 H22B 0.9800 C22 H22C 0.9800 C23 H23A 0.9800 C23 H23B 0.9800 C23 H23C 0.9800 C24 C29 1.394(2) C24 C25 1.3984(19) C25 C26 1.389(2) C25 H25 0.9500 C26 C27 1.385(2) C26 H26 0.9500 C27 C28 1.387(2) C27 H27 0.9500 C28 C29 1.391(2) C28 H28 0.9500 C29 H29 0.9500 C30 C31 1.393(2) C30 C35 1.397(2) C31 C32 1.396(2) C31 H31 0.9500 C32 C33 1.381(3) C32 H32 0.9500 C33 C34 1.379(3) C33 H33 0.9500 C34 C35 1.388(2) C34 H34 0.9500 C35 H35 0.9500