#------------------------------------------------------------------------------ #$Date: 2020-10-06 12:02:34 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257564 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/52/7705201.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_7705201 loop_ _publ_author_name 'Siewert, Jan-Erik' 'Schumann, Andr\'e' 'Fischer, Malte' 'Schmidt, Christoph' 'Taeufer, Tobias' 'Hering-Junghans, Christian' _publ_section_title ; Terphenyl(bisamino)phosphines: electron-rich ligands for gold-catalysis. ; _journal_issue 35 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 12354 _journal_page_last 12364 _journal_paper_doi 10.1039/d0dt02435j _journal_volume 49 _journal_year 2020 _chemical_formula_moiety 'C28 H37 N2 P' _chemical_formula_sum 'C28 H37 N2 P' _chemical_formula_weight 432.56 _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-2014/7 _audit_update_record ; 2020-07-07 deposited with the CCDC. 2020-08-18 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.6395(17) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.0222(5) _cell_length_b 8.2670(2) _cell_length_c 16.4946(4) _cell_measurement_reflns_used 9315 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 30.18 _cell_measurement_theta_min 2.71 _cell_volume 2445.63(11) _computing_cell_refinement 'SAINT (Bruker, 2013)' _computing_data_collection 'APEX2 (Bruker, 2014)' _computing_data_reduction SAINT _computing_molecular_graphics 'ORTEP-3v2.01 (Farrugia, 1997)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_av_unetI/netI 0.0232 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 39147 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.497 _diffrn_reflns_theta_min 2.271 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2014)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.175 _exptl_crystal_description prism _exptl_crystal_F_000 936 _exptl_crystal_size_max 0.464 _exptl_crystal_size_mid 0.176 _exptl_crystal_size_min 0.126 _refine_diff_density_max 0.309 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 290 _refine_ls_number_reflns 5619 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.019 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0409 _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^)+(0.0568P)^2^+1.3232P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1062 _refine_ls_wR_factor_ref 0.1169 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4653 _reflns_number_total 5619 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02435j2.cif _cod_data_source_block ax1653_TerP_NMe2_2_cmp1a _cod_depositor_comments 'Adding full bibliography for 7705201--7705209.cif.' _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7705201 _shelx_shelxl_version_number 2014/7 _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 0.942 _shelx_estimated_absorpt_t_max 0.984 _shelx_res_file ; AX1653.res created by SHELXL-2014/7 TITL shelxt_a.res in P2(1)/c CELL 0.71073 18.0222 8.2670 16.4946 90.000 95.6395 90.000 ZERR 4.00 0.0005 0.0002 0.0004 0.000 0.0017 0.000 LATT 1 SYMM - X, 1/2 + Y, 1/2 - Z SFAC C H N P UNIT 112 148 8 4 MERG 2 OMIT -4.00 55.00 OMIT 1 0 0 FMAP 2 PLAN 20 SIZE 0.126 0.176 0.464 ACTA BOND $H CONF LIST 6 L.S. 8 TEMP -123.15 WGHT 0.056800 1.323200 FVAR 0.14068 P1 4 0.231624 0.635247 0.505505 11.00000 0.01939 0.01793 = 0.02042 -0.00087 0.00375 -0.00034 N1 3 0.158610 0.639659 0.561690 11.00000 0.02436 0.02393 = 0.02636 -0.00162 0.00689 0.00123 N2 3 0.198149 0.650801 0.406778 11.00000 0.03087 0.02095 = 0.02177 0.00043 0.00104 -0.00130 C1 1 0.266096 0.423562 0.502740 11.00000 0.01755 0.01964 = 0.02226 -0.00288 0.00093 0.00015 C2 1 0.242175 0.285968 0.543393 11.00000 0.02001 0.02172 = 0.02429 -0.00124 0.00151 0.00021 C3 1 0.276562 0.136508 0.533069 11.00000 0.02772 0.02025 = 0.03618 0.00150 0.00383 0.00052 AFIX 43 H3 2 0.259775 0.044029 0.560174 11.00000 -1.20000 AFIX 0 C4 1 0.334219 0.120242 0.484505 11.00000 0.02728 0.02330 = 0.04724 -0.00480 0.00635 0.00597 AFIX 43 H4 2 0.355436 0.017087 0.476201 11.00000 -1.20000 AFIX 0 C5 1 0.360608 0.256375 0.448142 11.00000 0.02220 0.02998 = 0.03896 -0.00560 0.00999 0.00151 AFIX 43 H5 2 0.401244 0.246409 0.415900 11.00000 -1.20000 AFIX 0 C6 1 0.328913 0.407742 0.457758 11.00000 0.01982 0.02457 = 0.02663 -0.00392 0.00346 -0.00136 C7 1 0.182678 0.283237 0.601042 11.00000 0.02244 0.01681 = 0.02525 0.00267 0.00390 0.00163 C8 1 0.197637 0.347468 0.679894 11.00000 0.02570 0.01903 = 0.02465 0.00319 0.00072 0.00162 C9 1 0.143649 0.334975 0.734092 11.00000 0.03261 0.02293 = 0.02290 0.00216 0.00326 0.00230 AFIX 43 H9 2 0.153602 0.379339 0.787177 11.00000 -1.20000 AFIX 0 C10 1 0.075357 0.259478 0.713128 11.00000 0.02848 0.02414 = 0.02679 0.00626 0.00698 0.00371 C11 1 0.062692 0.192130 0.636112 11.00000 0.02417 0.02447 = 0.02886 0.00370 0.00384 -0.00193 AFIX 43 H11 2 0.016865 0.137999 0.621279 11.00000 -1.20000 AFIX 0 C12 1 0.115431 0.201619 0.579679 11.00000 0.02533 0.02012 = 0.02485 0.00057 0.00368 -0.00023 C13 1 0.271330 0.427000 0.705944 11.00000 0.02938 0.02751 = 0.02847 -0.00068 -0.00112 -0.00212 AFIX 137 H13A 2 0.272302 0.535247 0.681852 11.00000 -1.50000 H13B 2 0.311813 0.361701 0.687460 11.00000 -1.50000 H13C 2 0.277822 0.435800 0.765468 11.00000 -1.50000 AFIX 0 C14 1 0.016784 0.251251 0.772322 11.00000 0.03337 0.03846 = 0.02891 0.00512 0.01008 0.00364 AFIX 137 H14A 2 -0.010823 0.353496 0.771045 11.00000 -1.50000 H14B 2 0.040849 0.232571 0.827420 11.00000 -1.50000 H14C 2 -0.017731 0.162339 0.756965 11.00000 -1.50000 AFIX 0 C15 1 0.098155 0.124855 0.497078 11.00000 0.02877 0.03177 = 0.02880 -0.00309 0.00435 -0.00649 AFIX 137 H15A 2 0.116684 0.013339 0.498596 11.00000 -1.50000 H15B 2 0.122446 0.186585 0.456384 11.00000 -1.50000 H15C 2 0.044105 0.124737 0.482559 11.00000 -1.50000 AFIX 0 C16 1 0.367425 0.549394 0.423088 11.00000 0.02079 0.02489 = 0.02995 -0.00398 0.00913 -0.00042 C17 1 0.362720 0.576159 0.338947 11.00000 0.02905 0.03323 = 0.03190 -0.00610 0.01196 -0.00277 C18 1 0.402219 0.703466 0.308686 11.00000 0.03953 0.03522 = 0.03452 -0.00212 0.01696 -0.00177 AFIX 43 H18 2 0.398028 0.722352 0.251607 11.00000 -1.20000 AFIX 0 C19 1 0.447591 0.803663 0.359604 11.00000 0.03361 0.02673 = 0.04895 -0.00200 0.02060 -0.00194 C20 1 0.453146 0.772965 0.442469 11.00000 0.02382 0.02658 = 0.04350 -0.00807 0.00990 -0.00293 AFIX 43 H20 2 0.484440 0.839988 0.477937 11.00000 -1.20000 AFIX 0 C21 1 0.414471 0.647246 0.475731 11.00000 0.01778 0.02738 = 0.03432 -0.00591 0.00782 0.00082 C22 1 0.316918 0.469243 0.279414 11.00000 0.05128 0.05199 = 0.03140 -0.00925 0.01027 -0.01634 AFIX 137 H22A 2 0.294005 0.534971 0.234245 11.00000 -1.50000 H22B 2 0.277807 0.416092 0.307025 11.00000 -1.50000 H22C 2 0.349133 0.387084 0.258229 11.00000 -1.50000 AFIX 0 C23 1 0.489874 0.941548 0.325129 11.00000 0.06019 0.03739 = 0.06723 0.00054 0.03001 -0.01300 AFIX 137 H23A 2 0.458959 1.039286 0.322410 11.00000 -1.50000 H23B 2 0.502070 0.913151 0.270300 11.00000 -1.50000 H23C 2 0.535985 0.961528 0.360344 11.00000 -1.50000 AFIX 0 C24 1 0.425149 0.617486 0.565930 11.00000 0.02375 0.03681 = 0.03564 -0.00618 0.00103 -0.00254 AFIX 137 H24A 2 0.464469 0.688746 0.590805 11.00000 -1.50000 H24B 2 0.439496 0.504433 0.576192 11.00000 -1.50000 H24C 2 0.378453 0.639857 0.589660 11.00000 -1.50000 AFIX 0 C25 1 0.084448 0.578019 0.537684 11.00000 0.02141 0.03362 = 0.04326 0.00845 0.00651 0.00309 AFIX 137 H25A 2 0.062805 0.536076 0.585702 11.00000 -1.50000 H25B 2 0.087347 0.490852 0.497853 11.00000 -1.50000 H25C 2 0.053024 0.665431 0.513259 11.00000 -1.50000 AFIX 0 C26 1 0.160674 0.752291 0.629330 11.00000 0.04481 0.02838 = 0.02978 -0.00171 0.01510 0.00697 AFIX 137 H26A 2 0.124016 0.838365 0.616438 11.00000 -1.50000 H26B 2 0.210613 0.799687 0.638833 11.00000 -1.50000 H26C 2 0.148786 0.694899 0.678407 11.00000 -1.50000 AFIX 0 C27 1 0.196628 0.810275 0.370312 11.00000 0.06197 0.02571 = 0.02665 0.00434 0.00276 -0.00024 AFIX 137 H27A 2 0.212379 0.802939 0.315230 11.00000 -1.50000 H27B 2 0.230612 0.881982 0.403505 11.00000 -1.50000 H27C 2 0.145865 0.853817 0.367523 11.00000 -1.50000 AFIX 0 C28 1 0.148302 0.537943 0.361348 11.00000 0.03944 0.03116 = 0.02778 -0.00217 -0.00526 -0.00216 AFIX 137 H28A 2 0.096510 0.570220 0.365630 11.00000 -1.50000 H28B 2 0.156541 0.428909 0.383760 11.00000 -1.50000 H28C 2 0.158199 0.538499 0.303981 11.00000 -1.50000 AFIX 0 HKLF 4 REM shelxt_a.res in P2(1)/c REM R1 = 0.0409 for 4653 Fo > 4sig(Fo) and 0.0517 for all 5619 data REM 290 parameters refined using 0 restraints END WGHT 0.0568 1.3232 REM Highest difference peak 0.309, deepest hole -0.311, 1-sigma level 0.048 Q1 1 0.2462 0.5223 0.5004 11.00000 0.05 0.31 Q2 1 0.3494 0.4841 0.4417 11.00000 0.05 0.29 Q3 1 0.2111 0.2840 0.5723 11.00000 0.05 0.27 Q4 1 0.3316 0.4860 0.2255 11.00000 0.05 0.27 Q5 1 0.1775 0.3014 0.7082 11.00000 0.05 0.27 Q6 1 0.2315 0.3810 0.6909 11.00000 0.05 0.26 Q7 1 0.1021 0.3225 0.7175 11.00000 0.05 0.25 Q8 1 0.3636 0.5691 0.3852 11.00000 0.05 0.24 Q9 1 0.3771 0.6164 0.4493 11.00000 0.05 0.24 Q10 1 0.3384 0.3349 0.4481 11.00000 0.05 0.24 Q11 1 0.5371 0.9123 0.3158 11.00000 0.05 0.24 Q12 1 0.0215 0.1467 0.8013 11.00000 0.05 0.24 Q13 1 0.1894 0.7322 0.3878 11.00000 0.05 0.23 Q14 1 -0.0359 0.2655 0.7434 11.00000 0.05 0.23 Q15 1 0.1864 0.3379 0.6425 11.00000 0.05 0.22 Q16 1 0.2920 0.3697 0.3015 11.00000 0.05 0.22 Q17 1 0.1551 0.2184 0.5965 11.00000 0.05 0.22 Q18 1 0.4946 1.0392 0.3661 11.00000 0.05 0.22 Q19 1 0.2591 0.2136 0.5428 11.00000 0.05 0.22 Q20 1 0.2557 0.3609 0.5283 11.00000 0.05 0.22 ; _shelx_res_checksum 52273 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.23162(2) 0.63525(4) 0.50551(2) 0.01913(10) Uani 1 1 d . . . . . N1 N 0.15861(7) 0.63966(15) 0.56169(8) 0.0246(3) Uani 1 1 d . . . . . N2 N 0.19815(7) 0.65080(14) 0.40678(7) 0.0246(3) Uani 1 1 d . . . . . C1 C 0.26610(7) 0.42356(17) 0.50274(8) 0.0199(3) Uani 1 1 d . . . . . C2 C 0.24218(8) 0.28597(17) 0.54339(9) 0.0221(3) Uani 1 1 d . . . . . C3 C 0.27656(9) 0.13651(18) 0.53307(10) 0.0280(3) Uani 1 1 d . . . . . H3 H 0.2598 0.0440 0.5602 0.034 Uiso 1 1 calc R U . . . C4 C 0.33422(9) 0.12024(19) 0.48451(11) 0.0324(4) Uani 1 1 d . . . . . H4 H 0.3554 0.0171 0.4762 0.039 Uiso 1 1 calc R U . . . C5 C 0.36061(8) 0.25637(19) 0.44814(10) 0.0299(3) Uani 1 1 d . . . . . H5 H 0.4012 0.2464 0.4159 0.036 Uiso 1 1 calc R U . . . C6 C 0.32891(8) 0.40774(18) 0.45776(9) 0.0236(3) Uani 1 1 d . . . . . C7 C 0.18268(8) 0.28324(16) 0.60104(9) 0.0214(3) Uani 1 1 d . . . . . C8 C 0.19764(8) 0.34747(17) 0.67989(9) 0.0232(3) Uani 1 1 d . . . . . C9 C 0.14365(9) 0.33498(18) 0.73409(9) 0.0261(3) Uani 1 1 d . . . . . H9 H 0.1536 0.3793 0.7872 0.031 Uiso 1 1 calc R U . . . C10 C 0.07536(8) 0.25948(18) 0.71313(9) 0.0262(3) Uani 1 1 d . . . . . C11 C 0.06269(8) 0.19213(18) 0.63611(9) 0.0258(3) Uani 1 1 d . . . . . H11 H 0.0169 0.1380 0.6213 0.031 Uiso 1 1 calc R U . . . C12 C 0.11543(8) 0.20162(17) 0.57968(9) 0.0234(3) Uani 1 1 d . . . . . C13 C 0.27133(9) 0.42700(19) 0.70594(10) 0.0287(3) Uani 1 1 d . . . . . H13A H 0.2723 0.5352 0.6819 0.043 Uiso 1 1 calc R U . . . H13B H 0.3118 0.3617 0.6875 0.043 Uiso 1 1 calc R U . . . H13C H 0.2778 0.4358 0.7655 0.043 Uiso 1 1 calc R U . . . C14 C 0.01678(9) 0.2513(2) 0.77232(10) 0.0331(4) Uani 1 1 d . . . . . H14A H -0.0108 0.3535 0.7710 0.050 Uiso 1 1 calc R U . . . H14B H 0.0408 0.2326 0.8274 0.050 Uiso 1 1 calc R U . . . H14C H -0.0177 0.1623 0.7570 0.050 Uiso 1 1 calc R U . . . C15 C 0.09816(9) 0.1249(2) 0.49708(10) 0.0297(3) Uani 1 1 d . . . . . H15A H 0.1167 0.0133 0.4986 0.045 Uiso 1 1 calc R U . . . H15B H 0.1224 0.1866 0.4564 0.045 Uiso 1 1 calc R U . . . H15C H 0.0441 0.1247 0.4826 0.045 Uiso 1 1 calc R U . . . C16 C 0.36743(8) 0.54939(18) 0.42309(9) 0.0248(3) Uani 1 1 d . . . . . C17 C 0.36272(9) 0.5762(2) 0.33895(10) 0.0308(3) Uani 1 1 d . . . . . C18 C 0.40222(10) 0.7035(2) 0.30869(11) 0.0355(4) Uani 1 1 d . . . . . H18 H 0.3980 0.7224 0.2516 0.043 Uiso 1 1 calc R U . . . C19 C 0.44759(9) 0.8037(2) 0.35960(11) 0.0353(4) Uani 1 1 d . . . . . C20 C 0.45315(8) 0.77297(19) 0.44247(11) 0.0309(3) Uani 1 1 d . . . . . H20 H 0.4844 0.8400 0.4779 0.037 Uiso 1 1 calc R U . . . C21 C 0.41447(8) 0.64725(18) 0.47573(10) 0.0261(3) Uani 1 1 d . . . . . C22 C 0.31692(11) 0.4692(3) 0.27941(11) 0.0445(5) Uani 1 1 d . . . . . H22A H 0.2940 0.5350 0.2342 0.067 Uiso 1 1 calc R U . . . H22B H 0.2778 0.4161 0.3070 0.067 Uiso 1 1 calc R U . . . H22C H 0.3491 0.3871 0.2582 0.067 Uiso 1 1 calc R U . . . C23 C 0.48987(13) 0.9415(2) 0.32513(14) 0.0534(5) Uani 1 1 d . . . . . H23A H 0.4590 1.0393 0.3224 0.080 Uiso 1 1 calc R U . . . H23B H 0.5021 0.9132 0.2703 0.080 Uiso 1 1 calc R U . . . H23C H 0.5360 0.9615 0.3603 0.080 Uiso 1 1 calc R U . . . C24 C 0.42515(9) 0.6175(2) 0.56593(10) 0.0322(4) Uani 1 1 d . . . . . H24A H 0.4645 0.6887 0.5908 0.048 Uiso 1 1 calc R U . . . H24B H 0.4395 0.5044 0.5762 0.048 Uiso 1 1 calc R U . . . H24C H 0.3785 0.6399 0.5897 0.048 Uiso 1 1 calc R U . . . C25 C 0.08445(8) 0.5780(2) 0.53768(11) 0.0325(4) Uani 1 1 d . . . . . H25A H 0.0628 0.5361 0.5857 0.049 Uiso 1 1 calc R U . . . H25B H 0.0873 0.4909 0.4979 0.049 Uiso 1 1 calc R U . . . H25C H 0.0530 0.6654 0.5133 0.049 Uiso 1 1 calc R U . . . C26 C 0.16067(10) 0.7523(2) 0.62933(10) 0.0336(4) Uani 1 1 d . . . . . H26A H 0.1240 0.8384 0.6164 0.050 Uiso 1 1 calc R U . . . H26B H 0.2106 0.7997 0.6388 0.050 Uiso 1 1 calc R U . . . H26C H 0.1488 0.6949 0.6784 0.050 Uiso 1 1 calc R U . . . C27 C 0.19663(12) 0.8103(2) 0.37031(10) 0.0382(4) Uani 1 1 d . . . . . H27A H 0.2124 0.8029 0.3152 0.057 Uiso 1 1 calc R U . . . H27B H 0.2306 0.8820 0.4035 0.057 Uiso 1 1 calc R U . . . H27C H 0.1459 0.8538 0.3675 0.057 Uiso 1 1 calc R U . . . C28 C 0.14830(9) 0.5379(2) 0.36135(10) 0.0334(4) Uani 1 1 d . . . . . H28A H 0.0965 0.5702 0.3656 0.050 Uiso 1 1 calc R U . . . H28B H 0.1565 0.4289 0.3838 0.050 Uiso 1 1 calc R U . . . H28C H 0.1582 0.5385 0.3040 0.050 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 0.01939(18) 0.01793(18) 0.02042(18) -0.00087(13) 0.00375(13) -0.00034(13) N1 0.0244(6) 0.0239(6) 0.0264(6) -0.0016(5) 0.0069(5) 0.0012(5) N2 0.0309(6) 0.0209(6) 0.0218(6) 0.0004(5) 0.0010(5) -0.0013(5) C1 0.0176(6) 0.0196(6) 0.0223(7) -0.0029(5) 0.0009(5) 0.0001(5) C2 0.0200(6) 0.0217(7) 0.0243(7) -0.0012(5) 0.0015(5) 0.0002(5) C3 0.0277(7) 0.0202(7) 0.0362(8) 0.0015(6) 0.0038(6) 0.0005(6) C4 0.0273(8) 0.0233(8) 0.0472(10) -0.0048(7) 0.0064(7) 0.0060(6) C5 0.0222(7) 0.0300(8) 0.0390(9) -0.0056(7) 0.0100(6) 0.0015(6) C6 0.0198(6) 0.0246(7) 0.0266(7) -0.0039(6) 0.0035(5) -0.0014(5) C7 0.0224(7) 0.0168(6) 0.0253(7) 0.0027(5) 0.0039(5) 0.0016(5) C8 0.0257(7) 0.0190(7) 0.0247(7) 0.0032(5) 0.0007(6) 0.0016(5) C9 0.0326(8) 0.0229(7) 0.0229(7) 0.0022(6) 0.0033(6) 0.0023(6) C10 0.0285(7) 0.0241(7) 0.0268(8) 0.0063(6) 0.0070(6) 0.0037(6) C11 0.0242(7) 0.0245(7) 0.0289(8) 0.0037(6) 0.0038(6) -0.0019(6) C12 0.0253(7) 0.0201(7) 0.0249(7) 0.0006(5) 0.0037(6) -0.0002(5) C13 0.0294(7) 0.0275(8) 0.0285(8) -0.0007(6) -0.0011(6) -0.0021(6) C14 0.0334(8) 0.0385(9) 0.0289(8) 0.0051(7) 0.0101(7) 0.0036(7) C15 0.0288(7) 0.0318(8) 0.0288(8) -0.0031(6) 0.0044(6) -0.0065(6) C16 0.0208(6) 0.0249(7) 0.0300(8) -0.0040(6) 0.0091(6) -0.0004(6) C17 0.0290(8) 0.0332(8) 0.0319(8) -0.0061(7) 0.0120(6) -0.0028(6) C18 0.0395(9) 0.0352(9) 0.0345(9) -0.0021(7) 0.0170(7) -0.0018(7) C19 0.0336(8) 0.0267(8) 0.0489(10) -0.0020(7) 0.0206(8) -0.0019(7) C20 0.0238(7) 0.0266(8) 0.0435(9) -0.0081(7) 0.0099(7) -0.0029(6) C21 0.0178(6) 0.0274(7) 0.0343(8) -0.0059(6) 0.0078(6) 0.0008(5) C22 0.0513(11) 0.0520(11) 0.0314(9) -0.0093(8) 0.0103(8) -0.0163(9) C23 0.0602(13) 0.0374(10) 0.0672(14) 0.0005(10) 0.0300(11) -0.0130(9) C24 0.0238(7) 0.0368(9) 0.0356(9) -0.0062(7) 0.0010(6) -0.0025(6) C25 0.0214(7) 0.0336(8) 0.0433(9) 0.0085(7) 0.0065(6) 0.0031(6) C26 0.0448(9) 0.0284(8) 0.0298(8) -0.0017(6) 0.0151(7) 0.0070(7) C27 0.0620(12) 0.0257(8) 0.0267(8) 0.0043(6) 0.0028(8) -0.0002(8) C28 0.0394(9) 0.0312(8) 0.0278(8) -0.0022(6) -0.0053(7) -0.0022(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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 N2 107.79(6) . . ? N1 P1 C1 108.37(6) . . ? N2 P1 C1 97.87(6) . . ? C25 N1 C26 112.90(13) . . ? C25 N1 P1 126.32(11) . . ? C26 N1 P1 118.37(11) . . ? C27 N2 C28 112.66(13) . . ? C27 N2 P1 117.47(10) . . ? C28 N2 P1 126.48(10) . . ? C2 C1 C6 118.12(12) . . ? C2 C1 P1 129.01(10) . . ? C6 C1 P1 112.66(10) . . ? C3 C2 C1 119.65(13) . . ? C3 C2 C7 114.58(13) . . ? C1 C2 C7 125.75(12) . . ? C4 C3 C2 121.62(14) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 118.93(14) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 121.37(14) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C5 C6 C1 120.00(13) . . ? C5 C6 C16 116.58(13) . . ? C1 C6 C16 123.31(13) . . ? C12 C7 C8 119.79(13) . . ? C12 C7 C2 120.11(13) . . ? C8 C7 C2 119.74(12) . . ? C9 C8 C7 118.99(13) . . ? C9 C8 C13 120.19(13) . . ? C7 C8 C13 120.81(13) . . ? C8 C9 C10 122.11(14) . . ? C8 C9 H9 118.9 . . ? C10 C9 H9 118.9 . . ? C11 C10 C9 118.02(14) . . ? C11 C10 C14 120.85(14) . . ? C9 C10 C14 121.13(14) . . ? C10 C11 C12 121.81(14) . . ? C10 C11 H11 119.1 . . ? C12 C11 H11 119.1 . . ? C11 C12 C7 119.20(13) . . ? C11 C12 C15 119.02(13) . . ? C7 C12 C15 121.77(13) . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 H14A 109.5 . . ? C10 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C10 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C17 C16 C21 119.66(14) . . ? C17 C16 C6 121.02(13) . . ? C21 C16 C6 119.06(14) . . ? C18 C17 C16 119.49(15) . . ? C18 C17 C22 118.51(15) . . ? C16 C17 C22 121.99(15) . . ? C19 C18 C17 121.78(16) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C20 C19 C18 118.00(15) . . ? C20 C19 C23 121.27(17) . . ? C18 C19 C23 120.73(17) . . ? C19 C20 C21 122.35(15) . . ? C19 C20 H20 118.8 . . ? C21 C20 H20 118.8 . . ? C20 C21 C16 118.67(15) . . ? C20 C21 C24 119.46(14) . . ? C16 C21 C24 121.85(14) . . ? C17 C22 H22A 109.5 . . ? C17 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C17 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? N1 C25 H25A 109.5 . . ? N1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? N1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? N1 C26 H26A 109.5 . . ? N1 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? N1 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? N2 C27 H27A 109.5 . . ? N2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? N2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N2 C28 H28A 109.5 . . ? N2 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? N2 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.6827(12) . ? P1 N2 1.6850(13) . ? P1 C1 1.8591(14) . ? N1 C25 1.449(2) . ? N1 C26 1.451(2) . ? N2 C27 1.448(2) . ? N2 C28 1.4515(19) . ? C1 C2 1.409(2) . ? C1 C6 1.4193(19) . ? C2 C3 1.400(2) . ? C2 C7 1.5016(19) . ? C3 C4 1.380(2) . ? C3 H3 0.9500 . ? C4 C5 1.382(2) . ? C4 H4 0.9500 . ? C5 C6 1.391(2) . ? C5 H5 0.9500 . ? C6 C16 1.503(2) . ? C7 C12 1.402(2) . ? C7 C8 1.406(2) . ? C8 C9 1.388(2) . ? C8 C13 1.506(2) . ? C9 C10 1.393(2) . ? C9 H9 0.9500 . ? C10 C11 1.385(2) . ? C10 C14 1.508(2) . ? C11 C12 1.396(2) . ? C11 H11 0.9500 . ? C12 C15 1.508(2) . ? 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 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.400(2) . ? C16 C21 1.408(2) . ? C17 C18 1.390(2) . ? C17 C22 1.506(2) . ? C18 C19 1.388(3) . ? C18 H18 0.9500 . ? C19 C20 1.384(3) . ? C19 C23 1.513(2) . ? C20 C21 1.394(2) . ? C20 H20 0.9500 . ? C21 C24 1.502(2) . ? 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 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N2 P1 N1 C25 31.91(14) . . . . ? C1 P1 N1 C25 -73.05(14) . . . . ? N2 P1 N1 C26 -129.13(12) . . . . ? C1 P1 N1 C26 125.92(11) . . . . ? N1 P1 N2 C27 95.72(13) . . . . ? C1 P1 N2 C27 -152.04(13) . . . . ? N1 P1 N2 C28 -61.85(14) . . . . ? C1 P1 N2 C28 50.39(14) . . . . ? N1 P1 C1 C2 -4.28(15) . . . . ? N2 P1 C1 C2 -116.05(13) . . . . ? N1 P1 C1 C6 -178.90(10) . . . . ? N2 P1 C1 C6 69.33(11) . . . . ? C6 C1 C2 C3 -5.2(2) . . . . ? P1 C1 C2 C3 -179.54(11) . . . . ? C6 C1 C2 C7 172.84(13) . . . . ? P1 C1 C2 C7 -1.5(2) . . . . ? C1 C2 C3 C4 0.7(2) . . . . ? C7 C2 C3 C4 -177.52(14) . . . . ? C2 C3 C4 C5 2.8(2) . . . . ? C3 C4 C5 C6 -1.8(3) . . . . ? C4 C5 C6 C1 -2.8(2) . . . . ? C4 C5 C6 C16 173.53(15) . . . . ? C2 C1 C6 C5 6.2(2) . . . . ? P1 C1 C6 C5 -178.54(12) . . . . ? C2 C1 C6 C16 -169.85(13) . . . . ? P1 C1 C6 C16 5.41(18) . . . . ? C3 C2 C7 C12 -69.00(18) . . . . ? C1 C2 C7 C12 112.90(16) . . . . ? C3 C2 C7 C8 104.11(16) . . . . ? C1 C2 C7 C8 -73.99(19) . . . . ? C12 C7 C8 C9 -2.9(2) . . . . ? C2 C7 C8 C9 -176.05(13) . . . . ? C12 C7 C8 C13 176.35(13) . . . . ? C2 C7 C8 C13 3.2(2) . . . . ? C7 C8 C9 C10 0.6(2) . . . . ? C13 C8 C9 C10 -178.66(14) . . . . ? C8 C9 C10 C11 1.5(2) . . . . ? C8 C9 C10 C14 -178.38(14) . . . . ? C9 C10 C11 C12 -1.4(2) . . . . ? C14 C10 C11 C12 178.49(14) . . . . ? C10 C11 C12 C7 -0.8(2) . . . . ? C10 C11 C12 C15 179.68(14) . . . . ? C8 C7 C12 C11 3.0(2) . . . . ? C2 C7 C12 C11 176.13(13) . . . . ? C8 C7 C12 C15 -177.50(13) . . . . ? C2 C7 C12 C15 -4.4(2) . . . . ? C5 C6 C16 C17 73.64(19) . . . . ? C1 C6 C16 C17 -110.18(17) . . . . ? C5 C6 C16 C21 -100.37(17) . . . . ? C1 C6 C16 C21 75.81(19) . . . . ? C21 C16 C17 C18 -2.7(2) . . . . ? C6 C16 C17 C18 -176.65(14) . . . . ? C21 C16 C17 C22 176.32(15) . . . . ? C6 C16 C17 C22 2.3(2) . . . . ? C16 C17 C18 C19 1.2(3) . . . . ? C22 C17 C18 C19 -177.78(17) . . . . ? C17 C18 C19 C20 0.4(3) . . . . ? C17 C18 C19 C23 -179.89(17) . . . . ? C18 C19 C20 C21 -0.7(2) . . . . ? C23 C19 C20 C21 179.66(16) . . . . ? C19 C20 C21 C16 -0.8(2) . . . . ? C19 C20 C21 C24 177.95(15) . . . . ? C17 C16 C21 C20 2.4(2) . . . . ? C6 C16 C21 C20 176.53(13) . . . . ? C17 C16 C21 C24 -176.26(14) . . . . ? C6 C16 C21 C24 -2.2(2) . . . . ?