#------------------------------------------------------------------------------ #$Date: 2019-12-21 03:44:49 +0200 (Sat, 21 Dec 2019) $ #$Revision: 245463 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/56/7125675.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_7125675 loop_ _publ_author_name 'Livshits-Kritsman, Yulia' 'Tumanskii, Boris L.' 'Menard, Gabriel' 'Dobrovetsky, Roman' _publ_section_title ; Isolable Cyclic (Alkyl)(amino)carbene−Phosphonyl Radical Adducts ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C9CC09244G _journal_year 2020 _chemical_formula_moiety 'C26 H45 N O3 P' _chemical_formula_sum 'C26 H45 N O3 P' _chemical_formula_weight 450.60 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -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 90.3160(10) _cell_angle_beta 93.4380(10) _cell_angle_gamma 110.9860(10) _cell_formula_units_Z 2 _cell_length_a 9.5438(3) _cell_length_b 9.7293(3) _cell_length_c 15.4360(5) _cell_measurement_reflns_used 15574 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 28.462 _cell_measurement_theta_min 1.322 _cell_volume 1335.26(7) _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 0.993 _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 0.0226 _diffrn_reflns_av_unetI/netI 0.0337 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 15574 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.462 _diffrn_reflns_theta_min 1.322 _diffrn_source 'ImuS micro-focus' _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_correction_T_min 0.958 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sadabs, Bruker-AXS' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.121 _exptl_crystal_description prism _exptl_crystal_F_000 494 _exptl_crystal_size_max 0.335 _exptl_crystal_size_mid 0.221 _exptl_crystal_size_min 0.124 _refine_diff_density_max 0.362 _refine_diff_density_min -0.380 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 292 _refine_ls_number_reflns 6695 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0385 _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^)+(0.0459P)^2^+0.4033P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0952 _refine_ls_wR_factor_ref 0.1008 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5674 _reflns_number_total 6695 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9cc09244g2.cif _cod_data_source_block rom93 _cod_database_code 7125675 _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 0.958 _shelx_estimated_absorpt_t_max 0.984 _shelx_res_file ; TITL mo_rom93_0m_a.res in P-1 rom93.res created by SHELXL-2018/1 at 15:37:41 on 14-Nov-2019 REM Old TITL mo_rom93_0m in P-1 REM SHELXT solution in P-1 REM R1 0.122, Rweak 0.006, Alpha 0.059, Orientation as input REM Formula found by SHELXT: C26 N O3 P CELL 0.71073 9.5438 9.7293 15.4360 90.316 93.438 110.986 ZERR 2.000 0.0003 0.0003 0.0005 0.001 0.001 0.001 LATT 1 SFAC C H N O P UNIT 52 90 2 6 2 TEMP -163.000 SIZE 0.124 0.221 0.335 ACTA L.S. 10 BOND $H OMIT 0 -6 6 LIST 6 FMAP 2 PLAN 20 WGHT 0.045900 0.403300 FVAR 0.80737 P1 5 0.219696 0.132383 0.327510 11.00000 0.01348 0.01350 = 0.01316 0.00090 0.00057 0.00352 O2 4 0.147447 -0.020944 0.353859 11.00000 0.02224 0.01536 = 0.01931 0.00330 0.00244 0.00401 O3 4 0.211380 0.249592 0.397746 11.00000 0.01916 0.01591 = 0.01637 -0.00045 0.00498 0.00365 C4 1 0.097856 0.209423 0.461762 11.00000 0.01550 0.02387 = 0.01916 -0.00188 0.00514 0.00442 AFIX 13 H4 2 0.024878 0.107298 0.448344 11.00000 -1.20000 AFIX 0 C5 1 0.016090 0.316670 0.455937 11.00000 0.03668 0.06163 = 0.04135 0.00015 0.00613 0.03396 AFIX 137 H5A 2 -0.032334 0.310339 0.397487 11.00000 -1.50000 H5B 2 0.088036 0.416950 0.467894 11.00000 -1.50000 H5C 2 -0.060482 0.292301 0.498652 11.00000 -1.50000 AFIX 0 C6 1 0.176776 0.214786 0.549948 11.00000 0.02722 0.03458 = 0.01883 0.00504 0.00447 0.00674 AFIX 137 H6A 2 0.228262 0.143838 0.550741 11.00000 -1.50000 H6B 2 0.102821 0.189893 0.594190 11.00000 -1.50000 H6C 2 0.250564 0.314113 0.562259 11.00000 -1.50000 AFIX 0 O7 4 0.394481 0.186955 0.317628 11.00000 0.01390 0.02375 = 0.01380 0.00130 -0.00057 0.00632 C8 1 0.501781 0.197573 0.391477 11.00000 0.01620 0.02313 = 0.01527 0.00098 -0.00212 0.00791 AFIX 13 H8 2 0.453894 0.201208 0.446895 11.00000 -1.20000 AFIX 0 C9 1 0.546210 0.063599 0.388990 11.00000 0.03466 0.02837 = 0.03788 0.00259 -0.00626 0.01705 AFIX 137 H9A 2 0.456635 -0.025393 0.392810 11.00000 -1.50000 H9B 2 0.618272 0.069134 0.438071 11.00000 -1.50000 H9C 2 0.592575 0.060058 0.334473 11.00000 -1.50000 AFIX 0 C10 1 0.631967 0.339342 0.382140 11.00000 0.02395 0.02681 = 0.03582 0.00422 -0.01143 0.00305 AFIX 137 H10A 2 0.676994 0.336454 0.327065 11.00000 -1.50000 H10B 2 0.707480 0.351900 0.430383 11.00000 -1.50000 H10C 2 0.596236 0.422023 0.382891 11.00000 -1.50000 AFIX 0 C11 1 0.146778 0.166441 0.225725 11.00000 0.01276 0.01481 = 0.01518 0.00133 -0.00004 0.00180 C12 1 -0.001694 0.064024 0.182181 11.00000 0.01576 0.02075 = 0.01679 0.00209 -0.00256 -0.00155 C13 1 0.006161 -0.085519 0.156090 11.00000 0.03441 0.01849 = 0.02336 -0.00046 -0.00494 -0.00238 AFIX 137 H13A 2 -0.085858 -0.143386 0.121445 11.00000 -1.50000 H13B 2 0.015954 -0.138765 0.208443 11.00000 -1.50000 H13C 2 0.093397 -0.069805 0.121737 11.00000 -1.50000 AFIX 0 C14 1 -0.135859 0.035667 0.239323 11.00000 0.01425 0.03940 = 0.02701 0.00969 0.00035 -0.00193 AFIX 137 H14A 2 -0.145283 0.129631 0.254854 11.00000 -1.50000 H14B 2 -0.119148 -0.013002 0.292272 11.00000 -1.50000 H14C 2 -0.228396 -0.027648 0.207150 11.00000 -1.50000 AFIX 0 C15 1 -0.016400 0.150857 0.100587 11.00000 0.01727 0.02457 = 0.01840 0.00303 -0.00382 0.00024 AFIX 23 H15A 2 0.019924 0.113848 0.049929 11.00000 -1.20000 H15B 2 -0.122888 0.139148 0.087217 11.00000 -1.20000 AFIX 0 C16 1 0.079560 0.314066 0.120303 11.00000 0.01370 0.02296 = 0.01703 0.00241 -0.00224 0.00654 C17 1 -0.012488 0.395577 0.160915 11.00000 0.02068 0.03808 = 0.02985 0.00387 -0.00028 0.01783 AFIX 137 H17A 2 0.049344 0.500252 0.169048 11.00000 -1.50000 H17B 2 -0.044162 0.353795 0.217256 11.00000 -1.50000 H17C 2 -0.101451 0.384756 0.122385 11.00000 -1.50000 AFIX 0 C18 1 0.147189 0.393844 0.039376 11.00000 0.02127 0.02382 = 0.02052 0.00637 -0.00131 0.00737 AFIX 137 H18A 2 0.206108 0.342327 0.012990 11.00000 -1.50000 H18B 2 0.212662 0.495084 0.055501 11.00000 -1.50000 H18C 2 0.066234 0.395360 -0.002340 11.00000 -1.50000 AFIX 0 N19 3 0.197348 0.300833 0.184968 11.00000 0.01026 0.01475 = 0.01515 0.00185 -0.00039 0.00412 C20 1 0.354615 0.390956 0.184340 11.00000 0.01253 0.01219 = 0.01535 0.00380 0.00062 0.00374 C21 1 0.412447 0.524822 0.232621 11.00000 0.02078 0.01322 = 0.01764 0.00304 -0.00251 0.00513 C22 1 0.566765 0.605524 0.232711 11.00000 0.02339 0.01537 = 0.02530 0.00498 -0.00556 -0.00308 AFIX 43 H22 2 0.607596 0.696564 0.264519 11.00000 -1.20000 AFIX 0 C23 1 0.660998 0.556307 0.187842 11.00000 0.01385 0.02915 = 0.03184 0.01208 0.00015 -0.00159 AFIX 43 H23 2 0.765874 0.611618 0.190038 11.00000 -1.20000 AFIX 0 C24 1 0.602000 0.426248 0.139752 11.00000 0.01568 0.02961 = 0.02676 0.01055 0.00615 0.00886 AFIX 43 H24 2 0.667343 0.393757 0.108168 11.00000 -1.20000 AFIX 0 C25 1 0.449364 0.341161 0.136159 11.00000 0.01618 0.01667 = 0.01878 0.00610 0.00288 0.00745 C26 1 0.314983 0.585539 0.283041 11.00000 0.03002 0.01604 = 0.02104 -0.00253 -0.00258 0.01050 AFIX 13 H26 2 0.211610 0.508993 0.282066 11.00000 -1.20000 AFIX 0 C27 1 0.374613 0.623091 0.378110 11.00000 0.04298 0.02297 = 0.02292 -0.00414 -0.00260 0.01238 AFIX 137 H27A 2 0.475209 0.699548 0.380417 11.00000 -1.50000 H27B 2 0.379926 0.534667 0.405974 11.00000 -1.50000 H27C 2 0.306779 0.659033 0.408637 11.00000 -1.50000 AFIX 0 C28 1 0.304021 0.723685 0.239345 11.00000 0.05194 0.02232 = 0.03236 -0.00176 -0.00554 0.02141 AFIX 137 H28A 2 0.264333 0.698967 0.178947 11.00000 -1.50000 H28B 2 0.404164 0.800776 0.240707 11.00000 -1.50000 H28C 2 0.236595 0.759167 0.270591 11.00000 -1.50000 AFIX 0 C29 1 0.393102 0.200318 0.080405 11.00000 0.02563 0.02049 = 0.02039 0.00180 0.00657 0.01282 AFIX 13 H29 2 0.280666 0.162278 0.077440 11.00000 -1.20000 AFIX 0 C30 1 0.445222 0.080647 0.119792 11.00000 0.04974 0.02775 = 0.02654 0.00448 0.00935 0.02603 AFIX 137 H30A 2 0.406953 -0.008119 0.082123 11.00000 -1.50000 H30B 2 0.406585 0.057317 0.177420 11.00000 -1.50000 H30C 2 0.555383 0.116386 0.124963 11.00000 -1.50000 AFIX 0 C31 1 0.442863 0.228274 -0.012784 11.00000 0.04024 0.03446 = 0.02152 0.00495 0.00961 0.02210 AFIX 137 H31A 2 0.390827 0.139745 -0.049269 11.00000 -1.50000 H31B 2 0.551737 0.252118 -0.012551 11.00000 -1.50000 H31C 2 0.417750 0.310782 -0.035948 11.00000 -1.50000 AFIX 0 HKLF 4 REM mo_rom93_0m_a.res in P-1 REM R1 = 0.0385 for 5674 Fo > 4sig(Fo) and 0.0468 for all 6695 data REM 292 parameters refined using 0 restraints END WGHT 0.0459 0.4033 REM Highest difference peak 0.362, deepest hole -0.380, 1-sigma level 0.044 Q1 1 0.1776 0.1634 0.2778 11.00000 0.05 0.36 Q2 1 -0.0174 0.1059 0.1446 11.00000 0.05 0.33 Q3 1 0.4228 0.2673 0.1130 11.00000 0.05 0.31 Q4 1 0.3999 0.3683 0.1607 11.00000 0.05 0.30 Q5 1 0.3852 0.4590 0.2077 11.00000 0.05 0.29 Q6 1 0.3619 0.5526 0.2516 11.00000 0.05 0.29 Q7 1 0.0288 0.2331 0.1095 11.00000 0.05 0.26 Q8 1 0.3201 0.6580 0.2626 11.00000 0.05 0.26 Q9 1 0.0682 0.1138 0.2048 11.00000 0.05 0.26 Q10 1 0.1918 0.0371 0.3323 11.00000 0.05 0.26 Q11 1 0.1119 0.3622 0.0822 11.00000 0.05 0.25 Q12 1 -0.0598 0.0572 0.2108 11.00000 0.05 0.25 Q13 1 0.4933 0.5602 0.2354 11.00000 0.05 0.25 Q14 1 0.0037 -0.0044 0.1687 11.00000 0.05 0.25 Q15 1 0.2832 0.3503 0.1853 11.00000 0.05 0.25 Q16 1 0.4294 0.1503 0.1023 11.00000 0.05 0.24 Q17 1 0.5222 0.3953 0.1310 11.00000 0.05 0.24 Q18 1 0.0253 0.3388 0.1437 11.00000 0.05 0.24 Q19 1 0.0609 0.2645 0.4607 11.00000 0.05 0.24 Q20 1 0.2169 0.2029 0.3705 11.00000 0.05 0.23 ; _shelx_res_checksum 87063 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 0.21970(3) 0.13238(3) 0.32751(2) 0.01376(8) Uani 1 1 d . . O2 O 0.14745(10) -0.02094(9) 0.35386(5) 0.01966(19) Uani 1 1 d . . O3 O 0.21138(9) 0.24959(9) 0.39775(5) 0.01771(18) Uani 1 1 d . . C4 C 0.09786(14) 0.20942(14) 0.46176(8) 0.0201(2) Uani 1 1 d . . H4 H 0.024878 0.107298 0.448344 0.024 Uiso 1 1 calc R U C5 C 0.01609(19) 0.3167(2) 0.45594(11) 0.0419(4) Uani 1 1 d . . H5A H -0.032334 0.310339 0.397487 0.063 Uiso 1 1 calc R U H5B H 0.088036 0.416950 0.467894 0.063 Uiso 1 1 calc R U H5C H -0.060482 0.292301 0.498652 0.063 Uiso 1 1 calc R U C6 C 0.17678(16) 0.21479(16) 0.54995(8) 0.0279(3) Uani 1 1 d . . H6A H 0.228262 0.143838 0.550741 0.042 Uiso 1 1 calc R U H6B H 0.102821 0.189893 0.594190 0.042 Uiso 1 1 calc R U H6C H 0.250564 0.314113 0.562259 0.042 Uiso 1 1 calc R U O7 O 0.39448(9) 0.18695(9) 0.31763(5) 0.01733(18) Uani 1 1 d . . C8 C 0.50178(13) 0.19757(13) 0.39148(8) 0.0181(2) Uani 1 1 d . . H8 H 0.453894 0.201208 0.446895 0.022 Uiso 1 1 calc R U C9 C 0.54621(17) 0.06360(16) 0.38899(10) 0.0324(3) Uani 1 1 d . . H9A H 0.456635 -0.025393 0.392810 0.049 Uiso 1 1 calc R U H9B H 0.618272 0.069134 0.438071 0.049 Uiso 1 1 calc R U H9C H 0.592575 0.060058 0.334473 0.049 Uiso 1 1 calc R U C10 C 0.63197(16) 0.33934(15) 0.38214(10) 0.0311(3) Uani 1 1 d . . H10A H 0.676994 0.336454 0.327065 0.047 Uiso 1 1 calc R U H10B H 0.707480 0.351900 0.430383 0.047 Uiso 1 1 calc R U H10C H 0.596236 0.422023 0.382891 0.047 Uiso 1 1 calc R U C11 C 0.14678(13) 0.16644(12) 0.22573(7) 0.0152(2) Uani 1 1 d . . C12 C -0.00169(14) 0.06402(14) 0.18218(8) 0.0201(3) Uani 1 1 d . . C13 C 0.00616(17) -0.08552(14) 0.15609(9) 0.0290(3) Uani 1 1 d . . H13A H -0.085858 -0.143386 0.121445 0.043 Uiso 1 1 calc R U H13B H 0.015954 -0.138765 0.208443 0.043 Uiso 1 1 calc R U H13C H 0.093397 -0.069805 0.121737 0.043 Uiso 1 1 calc R U C14 C -0.13586(15) 0.03567(17) 0.23932(9) 0.0301(3) Uani 1 1 d . . H14A H -0.145283 0.129631 0.254854 0.045 Uiso 1 1 calc R U H14B H -0.119148 -0.013002 0.292272 0.045 Uiso 1 1 calc R U H14C H -0.228396 -0.027648 0.207150 0.045 Uiso 1 1 calc R U C15 C -0.01640(14) 0.15086(14) 0.10059(8) 0.0223(3) Uani 1 1 d . . H15A H 0.019924 0.113848 0.049929 0.027 Uiso 1 1 calc R U H15B H -0.122888 0.139148 0.087217 0.027 Uiso 1 1 calc R U C16 C 0.07956(13) 0.31407(14) 0.12030(8) 0.0180(2) Uani 1 1 d . . C17 C -0.01249(15) 0.39558(16) 0.16091(9) 0.0276(3) Uani 1 1 d . . H17A H 0.049344 0.500252 0.169048 0.041 Uiso 1 1 calc R U H17B H -0.044162 0.353795 0.217256 0.041 Uiso 1 1 calc R U H17C H -0.101451 0.384756 0.122385 0.041 Uiso 1 1 calc R U C18 C 0.14719(14) 0.39384(14) 0.03938(8) 0.0222(3) Uani 1 1 d . . H18A H 0.206108 0.342327 0.012990 0.033 Uiso 1 1 calc R U H18B H 0.212662 0.495084 0.055501 0.033 Uiso 1 1 calc R U H18C H 0.066234 0.395360 -0.002340 0.033 Uiso 1 1 calc R U N19 N 0.19735(10) 0.30083(10) 0.18497(6) 0.01354(19) Uani 1 1 d . . C20 C 0.35462(12) 0.39096(12) 0.18434(7) 0.0135(2) Uani 1 1 d . . C21 C 0.41245(14) 0.52482(12) 0.23262(8) 0.0176(2) Uani 1 1 d . . C22 C 0.56676(15) 0.60552(14) 0.23271(9) 0.0244(3) Uani 1 1 d . . H22 H 0.607596 0.696564 0.264519 0.029 Uiso 1 1 calc R U C23 C 0.66100(15) 0.55631(15) 0.18784(9) 0.0275(3) Uani 1 1 d . . H23 H 0.765874 0.611618 0.190038 0.033 Uiso 1 1 calc R U C24 C 0.60200(14) 0.42625(15) 0.13975(9) 0.0236(3) Uani 1 1 d . . H24 H 0.667343 0.393757 0.108168 0.028 Uiso 1 1 calc R U C25 C 0.44936(13) 0.34116(13) 0.13616(8) 0.0167(2) Uani 1 1 d . . C26 C 0.31498(16) 0.58554(14) 0.28304(8) 0.0220(3) Uani 1 1 d . . H26 H 0.211610 0.508993 0.282066 0.026 Uiso 1 1 calc R U C27 C 0.37461(18) 0.62309(15) 0.37811(9) 0.0297(3) Uani 1 1 d . . H27A H 0.475209 0.699548 0.380417 0.045 Uiso 1 1 calc R U H27B H 0.379926 0.534667 0.405974 0.045 Uiso 1 1 calc R U H27C H 0.306779 0.659033 0.408637 0.045 Uiso 1 1 calc R U C28 C 0.30402(19) 0.72368(15) 0.23934(10) 0.0337(3) Uani 1 1 d . . H28A H 0.264333 0.698967 0.178947 0.051 Uiso 1 1 calc R U H28B H 0.404164 0.800776 0.240707 0.051 Uiso 1 1 calc R U H28C H 0.236595 0.759167 0.270591 0.051 Uiso 1 1 calc R U C29 C 0.39310(15) 0.20032(14) 0.08040(8) 0.0207(3) Uani 1 1 d . . H29 H 0.280666 0.162278 0.077440 0.025 Uiso 1 1 calc R U C30 C 0.44522(19) 0.08065(16) 0.11979(9) 0.0310(3) Uani 1 1 d . . H30A H 0.406953 -0.008119 0.082123 0.047 Uiso 1 1 calc R U H30B H 0.406585 0.057317 0.177420 0.047 Uiso 1 1 calc R U H30C H 0.555383 0.116386 0.124963 0.047 Uiso 1 1 calc R U C31 C 0.44286(18) 0.22827(16) -0.01278(9) 0.0293(3) Uani 1 1 d . . H31A H 0.390827 0.139745 -0.049269 0.044 Uiso 1 1 calc R U H31B H 0.551737 0.252118 -0.012551 0.044 Uiso 1 1 calc R U H31C H 0.417750 0.310782 -0.035948 0.044 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 0.01348(15) 0.01350(14) 0.01316(14) 0.00090(10) 0.00057(11) 0.00352(11) O2 0.0222(5) 0.0154(4) 0.0193(4) 0.0033(3) 0.0024(3) 0.0040(3) O3 0.0192(4) 0.0159(4) 0.0164(4) -0.0004(3) 0.0050(3) 0.0036(3) C4 0.0155(6) 0.0239(6) 0.0192(6) -0.0019(5) 0.0051(5) 0.0044(5) C5 0.0367(9) 0.0616(11) 0.0414(9) 0.0001(8) 0.0061(7) 0.0340(9) C6 0.0272(7) 0.0346(7) 0.0188(6) 0.0050(5) 0.0045(5) 0.0067(6) O7 0.0139(4) 0.0237(4) 0.0138(4) 0.0013(3) -0.0006(3) 0.0063(3) C8 0.0162(6) 0.0231(6) 0.0153(5) 0.0010(5) -0.0021(4) 0.0079(5) C9 0.0347(8) 0.0284(7) 0.0379(8) 0.0026(6) -0.0063(6) 0.0171(6) C10 0.0240(7) 0.0268(7) 0.0358(8) 0.0042(6) -0.0114(6) 0.0030(6) C11 0.0128(5) 0.0148(5) 0.0152(5) 0.0013(4) 0.0000(4) 0.0018(4) C12 0.0158(6) 0.0207(6) 0.0168(6) 0.0021(5) -0.0026(5) -0.0015(5) C13 0.0344(8) 0.0185(6) 0.0234(6) -0.0005(5) -0.0049(6) -0.0024(6) C14 0.0142(6) 0.0394(8) 0.0270(7) 0.0097(6) 0.0003(5) -0.0019(6) C15 0.0173(6) 0.0246(6) 0.0184(6) 0.0030(5) -0.0038(5) 0.0002(5) C16 0.0137(6) 0.0230(6) 0.0170(5) 0.0024(5) -0.0022(4) 0.0065(5) C17 0.0207(7) 0.0381(8) 0.0299(7) 0.0039(6) -0.0003(5) 0.0178(6) C18 0.0213(6) 0.0238(6) 0.0205(6) 0.0064(5) -0.0013(5) 0.0074(5) N19 0.0103(4) 0.0148(4) 0.0152(4) 0.0018(4) -0.0004(4) 0.0041(4) C20 0.0125(5) 0.0122(5) 0.0153(5) 0.0038(4) 0.0006(4) 0.0037(4) C21 0.0208(6) 0.0132(5) 0.0176(5) 0.0030(4) -0.0025(5) 0.0051(5) C22 0.0234(7) 0.0154(6) 0.0253(6) 0.0050(5) -0.0056(5) -0.0031(5) C23 0.0139(6) 0.0291(7) 0.0318(7) 0.0121(6) 0.0002(5) -0.0016(5) C24 0.0157(6) 0.0296(7) 0.0268(6) 0.0105(5) 0.0062(5) 0.0089(5) C25 0.0162(6) 0.0167(5) 0.0188(5) 0.0061(4) 0.0029(4) 0.0075(5) C26 0.0300(7) 0.0160(6) 0.0210(6) -0.0025(5) -0.0026(5) 0.0105(5) C27 0.0430(9) 0.0230(6) 0.0229(6) -0.0041(5) -0.0026(6) 0.0124(6) C28 0.0519(10) 0.0223(7) 0.0324(7) -0.0018(6) -0.0055(7) 0.0214(7) C29 0.0256(7) 0.0205(6) 0.0204(6) 0.0018(5) 0.0066(5) 0.0128(5) C30 0.0497(9) 0.0277(7) 0.0265(7) 0.0045(6) 0.0093(6) 0.0260(7) C31 0.0402(8) 0.0345(7) 0.0215(6) 0.0050(6) 0.0096(6) 0.0221(7) 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 '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 O7 116.37(5) O2 P1 O3 112.87(5) O7 P1 O3 100.77(5) O2 P1 C11 112.79(5) O7 P1 C11 103.65(5) O3 P1 C11 109.35(5) C4 O3 P1 121.42(7) O3 C4 C6 108.02(10) O3 C4 C5 107.93(11) C6 C4 C5 112.27(12) O3 C4 H4 109.5 C6 C4 H4 109.5 C5 C4 H4 109.5 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 O7 P1 122.07(7) O7 C8 C10 106.20(9) O7 C8 C9 108.47(10) C10 C8 C9 113.06(11) O7 C8 H8 109.7 C10 C8 H8 109.7 C9 C8 H8 109.7 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 N19 C11 C12 111.06(9) N19 C11 P1 124.49(8) C12 C11 P1 123.04(8) C11 C12 C13 111.67(11) C11 C12 C14 113.23(11) C13 C12 C14 108.15(11) C11 C12 C15 101.40(9) C13 C12 C15 110.54(11) C14 C12 C15 111.79(11) C12 C13 H13A 109.5 C12 C13 H13B 109.5 H13A C13 H13B 109.5 C12 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C12 C14 H14A 109.5 C12 C14 H14B 109.5 H14A C14 H14B 109.5 C12 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C16 C15 C12 107.42(10) C16 C15 H15A 110.2 C12 C15 H15A 110.2 C16 C15 H15B 110.2 C12 C15 H15B 110.2 H15A C15 H15B 108.5 N19 C16 C18 112.18(10) N19 C16 C17 110.82(10) C18 C16 C17 108.97(10) N19 C16 C15 101.19(9) C18 C16 C15 112.21(10) C17 C16 C15 111.34(11) C16 C17 H17A 109.5 C16 C17 H17B 109.5 H17A C17 H17B 109.5 C16 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C16 C18 H18A 109.5 C16 C18 H18B 109.5 H18A C18 H18B 109.5 C16 C18 H18C 109.5 H18A C18 H18C 109.5 H18B C18 H18C 109.5 C11 N19 C20 122.68(9) C11 N19 C16 111.16(9) C20 N19 C16 123.29(9) C21 C20 C25 120.88(11) C21 C20 N19 120.14(10) C25 C20 N19 118.97(10) C22 C21 C20 118.03(11) C22 C21 C26 118.99(11) C20 C21 C26 122.98(11) C23 C22 C21 121.66(12) C23 C22 H22 119.2 C21 C22 H22 119.2 C22 C23 C24 119.50(12) C22 C23 H23 120.3 C24 C23 H23 120.3 C23 C24 C25 121.83(12) C23 C24 H24 119.1 C25 C24 H24 119.1 C24 C25 C20 118.07(11) C24 C25 C29 118.48(11) C20 C25 C29 123.45(11) C21 C26 C27 112.21(11) C21 C26 C28 110.04(11) C27 C26 C28 109.66(11) C21 C26 H26 108.3 C27 C26 H26 108.3 C28 C26 H26 108.3 C26 C27 H27A 109.5 C26 C27 H27B 109.5 H27A C27 H27B 109.5 C26 C27 H27C 109.5 H27A C27 H27C 109.5 H27B C27 H27C 109.5 C26 C28 H28A 109.5 C26 C28 H28B 109.5 H28A C28 H28B 109.5 C26 C28 H28C 109.5 H28A C28 H28C 109.5 H28B C28 H28C 109.5 C25 C29 C30 111.87(11) C25 C29 C31 111.71(11) C30 C29 C31 109.55(10) C25 C29 H29 107.8 C30 C29 H29 107.8 C31 C29 H29 107.8 C29 C30 H30A 109.5 C29 C30 H30B 109.5 H30A C30 H30B 109.5 C29 C30 H30C 109.5 H30A C30 H30C 109.5 H30B C30 H30C 109.5 C29 C31 H31A 109.5 C29 C31 H31B 109.5 H31A C31 H31B 109.5 C29 C31 H31C 109.5 H31A C31 H31C 109.5 H31B C31 H31C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 O2 1.4730(8) P1 O7 1.5763(9) P1 O3 1.5949(9) P1 C11 1.7614(11) O3 C4 1.4603(14) C4 C6 1.5070(18) C4 C5 1.5105(19) C4 H4 1.0000 C5 H5A 0.9800 C5 H5B 0.9800 C5 H5C 0.9800 C6 H6A 0.9800 C6 H6B 0.9800 C6 H6C 0.9800 O7 C8 1.4635(13) C8 C10 1.5044(18) C8 C9 1.5092(17) C8 H8 1.0000 C9 H9A 0.9800 C9 H9B 0.9800 C9 H9C 0.9800 C10 H10A 0.9800 C10 H10B 0.9800 C10 H10C 0.9800 C11 N19 1.3899(14) C11 C12 1.5230(16) C12 C13 1.5362(19) C12 C14 1.5423(18) C12 C15 1.5476(16) C13 H13A 0.9800 C13 H13B 0.9800 C13 H13C 0.9800 C14 H14A 0.9800 C14 H14B 0.9800 C14 H14C 0.9800 C15 C16 1.5403(17) C15 H15A 0.9900 C15 H15B 0.9900 C16 N19 1.4990(14) C16 C18 1.5258(17) C16 C17 1.5340(18) C17 H17A 0.9800 C17 H17B 0.9800 C17 H17C 0.9800 C18 H18A 0.9800 C18 H18B 0.9800 C18 H18C 0.9800 N19 C20 1.4425(14) C20 C21 1.4076(16) C20 C25 1.4128(16) C21 C22 1.3989(18) C21 C26 1.5150(17) C22 C23 1.377(2) C22 H22 0.9500 C23 C24 1.378(2) C23 H23 0.9500 C24 C25 1.3916(17) C24 H24 0.9500 C25 C29 1.5203(17) C26 C27 1.5349(18) C26 C28 1.5410(17) C26 H26 1.0000 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 C30 1.5359(17) C29 C31 1.5370(18) C29 H29 1.0000 C30 H30A 0.9800 C30 H30B 0.9800 C30 H30C 0.9800 C31 H31A 0.9800 C31 H31B 0.9800 C31 H31C 0.9800