#------------------------------------------------------------------------------ #$Date: 2024-02-04 14:31:54 +0200 (Sun, 04 Feb 2024) $ #$Revision: 289644 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247861.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_7247861 loop_ _publ_author_name 'Tichotová, Markéta Christou' 'Tučková, Lucie' 'Kocek, Hugo' 'Růžička, Aleš' 'Straka, Michal' 'Procházková, Eliška' _publ_section_title ; Exploring the impact of alignment media on RDC analysis of phosphorus-containing compounds: a molecular docking approach. ; _journal_issue 3 _journal_name_full 'Physical chemistry chemical physics : PCCP' _journal_page_first 2016 _journal_page_last 2024 _journal_paper_doi 10.1039/d3cp04099b _journal_volume 26 _journal_year 2024 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C16 H21 O3 P' _chemical_formula_sum 'C16 H21 O3 P' _chemical_formula_weight 292.30 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/1 _audit_update_record ; 2023-08-11 deposited with the CCDC. 2023-12-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 9.9495(2) _cell_length_b 11.5590(2) _cell_length_c 26.1562(5) _cell_measurement_reflns_used 64670 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 1 _cell_volume 3008.13(10) _computing_cell_refinement 'APEX4 v2021.4-1 (Bruker AXS)' _computing_data_collection 'Bruker Instrument Service vV6.2.3' _computing_data_reduction 'SAINT V8.40B (Bruker AXS Inc., 2019)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2019/1 (Sheldrick, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2014)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 10.4167 _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker D8 - Venture' _diffrn_measurement_method '\f and \w scans to fill the Ewald sphere' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0362 _diffrn_reflns_av_unetI/netI 0.0180 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 64670 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.994 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.287 _diffrn_reflns_theta_min 2.190 _diffrn_source 'sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.187 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.6693 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.291 _exptl_crystal_description block _exptl_crystal_F_000 1248 _exptl_crystal_size_max 0.587 _exptl_crystal_size_mid 0.442 _exptl_crystal_size_min 0.372 _refine_diff_density_max 0.180 _refine_diff_density_min -0.214 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack x determined using 3121 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.001(12) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 367 _refine_ls_number_reflns 7451 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.066 _refine_ls_R_factor_all 0.0261 _refine_ls_R_factor_gt 0.0251 _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^)+(0.0413P)^2^+0.3249P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.0686 _reflns_Friedel_coverage 0.780 _reflns_Friedel_fraction_full 0.992 _reflns_Friedel_fraction_max 0.993 _reflns_number_gt 7235 _reflns_number_total 7451 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3cp04099b2.cif _cod_data_source_block ar230510P1 _cod_depositor_comments 'Adding full bibliography for 7247861--7247864.cif.' _cod_database_code 7247861 _shelx_shelxl_version_number 2019/1 _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. ; _exptl_absorpt_special_details ; The ratio of minimum to maximum apparent transmission was 0.897 ; _shelx_res_file ; TITL mo_ar230510P1_0m_a.res in P2(1)2(1)2(1) shelxl.res created by SHELXL-2019/1 at 21:08:27 on 27-Jun-2023 REM Old TITL mo_ar230510P1_0m in P2(1)2(1)2(1) REM SHELXT solution in P2(1)2(1)2(1): R1 0.102, Rweak 0.027, Alpha 0.002 REM 3.551 for 26 systematic absences, Orientation as input REM Flack x = 0.027 ( 0.011 ) from 2582 Parsons' quotients REM Formula found by SHELXT: C32 O6 P2 CELL 0.71073 9.9495 11.5590 26.1562 90.000 90.000 90.000 ZERR 8.000 0.0002 0.0002 0.0005 0.000 0.000 0.000 LATT -1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H O P UNIT 128 168 24 8 ACTA LIST 4 TEMP -123.150 L.S. 10 BOND REM LIST 6 FMAP 2 OMIT 0 1 1 PLAN 20 WGHT 0.041300 0.324900 FVAR 0.47140 P1 4 0.290418 0.208353 0.840886 11.00000 0.03128 0.02283 = 0.02933 0.00035 -0.00594 -0.00080 P1A 4 0.119834 0.501893 0.565829 11.00000 0.02341 0.02246 = 0.02855 -0.00421 -0.00117 -0.00269 O1 3 0.291983 0.281925 0.886554 11.00000 0.06888 0.02931 = 0.03670 -0.00573 -0.01353 0.00255 O2 3 0.220058 0.085680 0.846703 11.00000 0.02420 0.02310 = 0.02989 0.00235 0.00161 0.00237 O1A 3 0.027768 0.418417 0.589420 11.00000 0.03654 0.03207 = 0.04282 -0.00633 0.00747 -0.01103 O3 3 0.431745 0.161103 0.821431 11.00000 0.02452 0.02674 = 0.04744 0.00846 -0.00645 -0.00390 O2A 3 0.219148 0.566868 0.604011 11.00000 0.02546 0.01937 = 0.02876 -0.00329 -0.00567 0.00210 O3A 3 0.053800 0.613108 0.540855 11.00000 0.02772 0.02666 = 0.03634 -0.00594 -0.01192 0.00046 C1 1 0.320157 -0.002752 0.861149 11.00000 0.02477 0.02288 = 0.02450 0.00093 -0.00227 0.00065 C8A 1 0.372158 0.752840 0.560480 11.00000 0.02348 0.03337 = 0.03516 -0.00424 0.00483 -0.00327 AFIX 23 H8AA 2 0.469372 0.771092 0.560220 11.00000 -1.20000 H8AB 2 0.353044 0.680487 0.541575 11.00000 -1.20000 AFIX 0 C10 1 0.341485 -0.324521 0.819354 11.00000 0.06123 0.02559 = 0.04805 -0.00552 0.00540 0.00305 AFIX 137 H10A 2 0.304875 -0.358249 0.850781 11.00000 -1.50000 H10B 2 0.414193 -0.373661 0.806420 11.00000 -1.50000 H10C 2 0.270251 -0.319129 0.793588 11.00000 -1.50000 AFIX 0 C2 1 0.456134 0.042285 0.838284 11.00000 0.02300 0.02702 = 0.04124 0.00734 -0.00573 -0.00184 AFIX 13 H2 2 0.525108 0.043530 0.866087 11.00000 -1.20000 AFIX 0 C1A 1 0.178539 0.687904 0.613586 11.00000 0.02060 0.01834 = 0.02500 -0.00063 -0.00192 0.00141 C3 1 0.512129 -0.028034 0.792877 11.00000 0.03548 0.04126 = 0.06073 0.00883 0.01956 0.00353 AFIX 23 H3A 2 0.514217 0.021984 0.762163 11.00000 -1.20000 H3B 2 0.605712 -0.051242 0.800636 11.00000 -1.20000 AFIX 0 C2A 1 0.084329 0.720526 0.567742 11.00000 0.02125 0.02339 = 0.02915 -0.00256 -0.00536 0.00073 AFIX 13 H2A 2 -0.001290 0.752739 0.581825 11.00000 -1.20000 AFIX 0 C4 1 0.430228 -0.135614 0.781071 11.00000 0.04856 0.03380 = 0.03560 -0.00001 0.01442 0.00962 AFIX 13 H4 2 0.464389 -0.183734 0.752078 11.00000 -1.20000 AFIX 0 C3A 1 0.143544 0.808758 0.529643 11.00000 0.03431 0.03052 = 0.02923 0.00425 -0.00645 0.00012 AFIX 23 H3AA 2 0.151943 0.771494 0.495714 11.00000 -1.20000 H3AB 2 0.080302 0.874406 0.526148 11.00000 -1.20000 AFIX 0 C5 1 0.396439 -0.203342 0.830727 11.00000 0.03565 0.02513 = 0.03336 -0.00015 0.00412 0.00487 C4A 1 0.280836 0.855345 0.545641 11.00000 0.03462 0.02877 = 0.03028 0.00259 0.00255 -0.00674 AFIX 13 H4A 2 0.321828 0.912843 0.521706 11.00000 -1.20000 AFIX 0 C6 1 0.276692 -0.115374 0.836602 11.00000 0.02476 0.02331 = 0.02811 -0.00130 -0.00033 -0.00032 AFIX 13 H6 2 0.191651 -0.149165 0.850467 11.00000 -1.20000 AFIX 0 C5A 1 0.280728 0.891126 0.603153 11.00000 0.02899 0.02143 = 0.03351 -0.00092 -0.00259 -0.00314 C7 1 0.319826 -0.007990 0.919280 11.00000 0.05628 0.03198 = 0.02390 -0.00031 -0.00474 0.00530 AFIX 137 H7A 2 0.381635 -0.068673 0.930762 11.00000 -1.50000 H7B 2 0.228848 -0.025423 0.931397 11.00000 -1.50000 H7C 2 0.348780 0.066752 0.933119 11.00000 -1.50000 AFIX 0 C6A 1 0.306270 0.759101 0.614018 11.00000 0.01868 0.02272 = 0.02837 -0.00296 -0.00206 -0.00077 AFIX 13 H6A 2 0.368287 0.742760 0.643224 11.00000 -1.20000 AFIX 0 C8 1 0.280940 -0.101724 0.777780 11.00000 0.04757 0.03333 = 0.02754 -0.00440 -0.00605 0.00449 AFIX 23 H8A 2 0.224338 -0.157983 0.759048 11.00000 -1.20000 H8B 2 0.265073 -0.021754 0.765648 11.00000 -1.20000 AFIX 0 C7A 1 0.106957 0.687822 0.664767 11.00000 0.03117 0.02651 = 0.02822 0.00010 0.00363 0.00009 AFIX 137 H7AA 2 0.082565 0.767261 0.674002 11.00000 -1.50000 H7AB 2 0.166597 0.655629 0.690972 11.00000 -1.50000 H7AC 2 0.025449 0.640523 0.662404 11.00000 -1.50000 AFIX 0 C9 1 0.505741 -0.214442 0.871202 11.00000 0.04161 0.03638 = 0.05372 0.00541 -0.00724 0.01181 AFIX 137 H9A 2 0.538794 -0.137326 0.880385 11.00000 -1.50000 H9B 2 0.580067 -0.260848 0.857642 11.00000 -1.50000 H9C 2 0.468688 -0.252293 0.901621 11.00000 -1.50000 AFIX 0 C9A 1 0.158192 0.953894 0.624117 11.00000 0.03904 0.02316 = 0.04304 -0.00320 -0.00125 0.00495 AFIX 137 H9AA 2 0.166109 0.960944 0.661333 11.00000 -1.50000 H9AB 2 0.076899 0.910003 0.615670 11.00000 -1.50000 H9AC 2 0.152617 1.031175 0.608856 11.00000 -1.50000 AFIX 0 C11 1 0.213263 0.279279 0.788099 11.00000 0.02475 0.02495 = 0.03187 0.00437 -0.00074 -0.00229 C10A 1 0.405397 0.961433 0.617450 11.00000 0.04042 0.03188 = 0.05554 -0.00628 -0.00370 -0.01291 AFIX 137 H10D 2 0.410365 0.969295 0.654708 11.00000 -1.50000 H10E 2 0.399717 1.038343 0.601831 11.00000 -1.50000 H10F 2 0.485999 0.921716 0.604973 11.00000 -1.50000 AFIX 0 C12 1 0.196764 0.226468 0.740609 11.00000 0.05000 0.02918 = 0.03553 0.00140 -0.00954 0.00335 AFIX 43 H12 2 0.232092 0.151257 0.734790 11.00000 -1.20000 AFIX 0 C11A 1 0.221158 0.435418 0.518029 11.00000 0.02669 0.02608 = 0.02973 -0.00666 -0.00215 -0.00094 C13 1 0.128663 0.283807 0.701788 11.00000 0.05533 0.03857 = 0.03780 0.00516 -0.01603 -0.00509 AFIX 43 H13 2 0.117553 0.247708 0.669434 11.00000 -1.20000 AFIX 0 C12A 1 0.262248 0.494036 0.474110 11.00000 0.03630 0.03316 = 0.03125 -0.00511 0.00039 -0.00513 AFIX 43 H12A 2 0.234229 0.571474 0.468240 11.00000 -1.20000 AFIX 0 C14 1 0.076809 0.393638 0.710110 11.00000 0.03122 0.03778 = 0.04935 0.01896 -0.00760 -0.00462 AFIX 43 H14 2 0.028651 0.431985 0.683720 11.00000 -1.20000 AFIX 0 C13A 1 0.344765 0.437941 0.438937 11.00000 0.04284 0.05242 = 0.03408 -0.01141 0.00628 -0.00860 AFIX 43 H13A 2 0.372803 0.477545 0.408952 11.00000 -1.20000 AFIX 0 C15 1 0.095181 0.446895 0.756563 11.00000 0.03613 0.02966 = 0.05056 0.01296 0.00591 0.00439 AFIX 43 H15 2 0.060723 0.522541 0.762022 11.00000 -1.20000 AFIX 0 C14A 1 0.386273 0.325524 0.447127 11.00000 0.04010 0.05565 = 0.04422 -0.02277 0.00411 0.00356 AFIX 43 H14A 2 0.443597 0.288533 0.423117 11.00000 -1.20000 AFIX 0 C16 1 0.164003 0.390618 0.795668 11.00000 0.03580 0.02620 = 0.03776 0.00446 0.00394 0.00098 AFIX 43 H16 2 0.177343 0.428276 0.827550 11.00000 -1.20000 AFIX 0 C15A 1 0.344454 0.267049 0.490167 11.00000 0.05128 0.03754 = 0.05160 -0.01531 -0.00377 0.01280 AFIX 43 H15A 2 0.372789 0.189561 0.495676 11.00000 -1.20000 AFIX 0 C16A 1 0.261283 0.320580 0.525484 11.00000 0.04473 0.02858 = 0.03653 -0.00510 -0.00299 0.00383 AFIX 43 H16A 2 0.231484 0.279302 0.554774 11.00000 -1.20000 AFIX 0 HKLF 4 REM mo_ar230510P1_0m_a.res in P2(1)2(1)2(1) REM wR2 = 0.0686, GooF = S = 1.066, Restrained GooF = 1.066 for all data REM R1 = 0.0251 for 7235 Fo > 4sig(Fo) and 0.0261 for all 7451 data REM 367 parameters refined using 0 restraints END WGHT 0.0412 0.3252 REM Highest difference peak 0.180, deepest hole -0.214, 1-sigma level 0.035 Q1 1 0.1360 0.7022 0.5918 11.00000 0.05 0.18 Q2 1 0.3196 -0.0046 0.8907 11.00000 0.05 0.17 Q3 1 0.2180 0.9168 0.6141 11.00000 0.05 0.17 Q4 1 0.1398 0.6868 0.6364 11.00000 0.05 0.17 Q5 1 0.2448 0.7243 0.6132 11.00000 0.05 0.17 Q6 1 0.3396 0.7453 0.5890 11.00000 0.05 0.15 Q7 1 0.4269 -0.1742 0.8051 11.00000 0.05 0.15 Q8 1 0.2722 -0.1066 0.8056 11.00000 0.05 0.15 Q9 1 0.2825 0.8248 0.6134 11.00000 0.05 0.15 Q10 1 0.3492 0.9167 0.6126 11.00000 0.05 0.14 Q11 1 0.2579 0.3781 0.5239 11.00000 0.05 0.13 Q12 1 0.1157 0.7597 0.5490 11.00000 0.05 0.13 Q13 1 0.2064 0.8228 0.5384 11.00000 0.05 0.13 Q14 1 0.1830 0.4742 0.5387 11.00000 0.05 0.13 Q15 1 0.3875 0.0132 0.8467 11.00000 0.05 0.13 Q16 1 0.2034 0.2570 0.7661 11.00000 0.05 0.13 Q17 1 0.4785 -0.0930 0.7865 11.00000 0.05 0.13 Q18 1 0.3273 0.7988 0.5503 11.00000 0.05 0.12 Q19 1 0.2800 0.8776 0.5759 11.00000 0.05 0.12 Q20 1 0.2674 0.4640 0.4982 11.00000 0.05 0.12 ; _shelx_res_checksum 23393 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.29042(4) 0.20835(3) 0.84089(2) 0.02781(9) Uani 1 1 d . . . . . P1A P 0.11983(4) 0.50189(3) 0.56583(2) 0.02481(8) Uani 1 1 d . . . . . O1 O 0.29198(17) 0.28192(11) 0.88655(5) 0.0450(3) Uani 1 1 d . . . . . O2 O 0.22006(11) 0.08568(9) 0.84670(4) 0.0257(2) Uani 1 1 d . . . . . O1A O 0.02777(13) 0.41842(11) 0.58942(5) 0.0371(3) Uani 1 1 d . . . . . O3 O 0.43175(11) 0.16110(10) 0.82143(5) 0.0329(2) Uani 1 1 d . . . . . O2A O 0.21915(11) 0.56687(8) 0.60401(4) 0.0245(2) Uani 1 1 d . . . . . O3A O 0.05380(11) 0.61311(10) 0.54086(4) 0.0302(2) Uani 1 1 d . . . . . C1 C 0.32016(14) -0.00275(13) 0.86115(5) 0.0240(3) Uani 1 1 d . . . . . C8A C 0.37216(16) 0.75284(14) 0.56048(6) 0.0307(3) Uani 1 1 d . . . . . H8AA H 0.469372 0.771092 0.560220 0.037 Uiso 1 1 calc R U . . . H8AB H 0.353044 0.680487 0.541575 0.037 Uiso 1 1 calc R U . . . C10 C 0.3415(2) -0.32452(15) 0.81935(8) 0.0450(4) Uani 1 1 d . . . . . H10A H 0.304875 -0.358249 0.850781 0.067 Uiso 1 1 calc R U . . . H10B H 0.414193 -0.373661 0.806420 0.067 Uiso 1 1 calc R U . . . H10C H 0.270251 -0.319129 0.793588 0.067 Uiso 1 1 calc R U . . . C2 C 0.45613(15) 0.04229(14) 0.83828(7) 0.0304(3) Uani 1 1 d . . . . . H2 H 0.525108 0.043530 0.866087 0.037 Uiso 1 1 calc R U . . . C1A C 0.17854(14) 0.68790(11) 0.61359(5) 0.0213(3) Uani 1 1 d . . . . . C3 C 0.5121(2) -0.02803(17) 0.79288(8) 0.0458(5) Uani 1 1 d . . . . . H3A H 0.514217 0.021984 0.762163 0.055 Uiso 1 1 calc R U . . . H3B H 0.605712 -0.051242 0.800636 0.055 Uiso 1 1 calc R U . . . C2A C 0.08433(14) 0.72053(12) 0.56774(5) 0.0246(3) Uani 1 1 d . . . . . H2A H -0.001290 0.752739 0.581825 0.030 Uiso 1 1 calc R U . . . C4 C 0.4302(2) -0.13561(16) 0.78107(7) 0.0393(4) Uani 1 1 d . . . . . H4 H 0.464389 -0.183734 0.752078 0.047 Uiso 1 1 calc R U . . . C3A C 0.14354(17) 0.80876(14) 0.52964(6) 0.0314(3) Uani 1 1 d . . . . . H3AA H 0.151943 0.771494 0.495714 0.038 Uiso 1 1 calc R U . . . H3AB H 0.080302 0.874406 0.526148 0.038 Uiso 1 1 calc R U . . . C5 C 0.39644(17) -0.20334(14) 0.83073(6) 0.0314(3) Uani 1 1 d . . . . . C4A C 0.28084(18) 0.85534(14) 0.54564(6) 0.0312(3) Uani 1 1 d . . . . . H4A H 0.321828 0.912843 0.521706 0.037 Uiso 1 1 calc R U . . . C6 C 0.27669(15) -0.11537(12) 0.83660(6) 0.0254(3) Uani 1 1 d . . . . . H6 H 0.191651 -0.149165 0.850467 0.030 Uiso 1 1 calc R U . . . C5A C 0.28073(17) 0.89113(13) 0.60315(6) 0.0280(3) Uani 1 1 d . . . . . C7 C 0.3198(2) -0.00799(16) 0.91928(6) 0.0374(4) Uani 1 1 d . . . . . H7A H 0.381635 -0.068673 0.930762 0.056 Uiso 1 1 calc R U . . . H7B H 0.228848 -0.025423 0.931397 0.056 Uiso 1 1 calc R U . . . H7C H 0.348780 0.066752 0.933119 0.056 Uiso 1 1 calc R U . . . C6A C 0.30627(14) 0.75910(12) 0.61402(5) 0.0233(3) Uani 1 1 d . . . . . H6A H 0.368287 0.742760 0.643224 0.028 Uiso 1 1 calc R U . . . C8 C 0.2809(2) -0.10172(16) 0.77778(6) 0.0361(4) Uani 1 1 d . . . . . H8A H 0.224338 -0.157983 0.759048 0.043 Uiso 1 1 calc R U . . . H8B H 0.265073 -0.021754 0.765648 0.043 Uiso 1 1 calc R U . . . C7A C 0.10696(16) 0.68782(13) 0.66477(6) 0.0286(3) Uani 1 1 d . . . . . H7AA H 0.082565 0.767261 0.674002 0.043 Uiso 1 1 calc R U . . . H7AB H 0.166597 0.655629 0.690972 0.043 Uiso 1 1 calc R U . . . H7AC H 0.025449 0.640523 0.662404 0.043 Uiso 1 1 calc R U . . . C9 C 0.5057(2) -0.21444(18) 0.87120(8) 0.0439(4) Uani 1 1 d . . . . . H9A H 0.538794 -0.137326 0.880385 0.066 Uiso 1 1 calc R U . . . H9B H 0.580067 -0.260848 0.857642 0.066 Uiso 1 1 calc R U . . . H9C H 0.468688 -0.252293 0.901621 0.066 Uiso 1 1 calc R U . . . C9A C 0.15819(18) 0.95389(14) 0.62412(7) 0.0351(3) Uani 1 1 d . . . . . H9AA H 0.166109 0.960944 0.661333 0.053 Uiso 1 1 calc R U . . . H9AB H 0.076899 0.910003 0.615670 0.053 Uiso 1 1 calc R U . . . H9AC H 0.152617 1.031175 0.608856 0.053 Uiso 1 1 calc R U . . . C11 C 0.21326(15) 0.27928(13) 0.78810(6) 0.0272(3) Uani 1 1 d . . . . . C10A C 0.4054(2) 0.96143(16) 0.61745(8) 0.0426(4) Uani 1 1 d . . . . . H10D H 0.410365 0.969295 0.654708 0.064 Uiso 1 1 calc R U . . . H10E H 0.399717 1.038343 0.601831 0.064 Uiso 1 1 calc R U . . . H10F H 0.485999 0.921716 0.604973 0.064 Uiso 1 1 calc R U . . . C12 C 0.1968(2) 0.22647(15) 0.74061(7) 0.0382(4) Uani 1 1 d . . . . . H12 H 0.232092 0.151257 0.734790 0.046 Uiso 1 1 calc R U . . . C11A C 0.22116(16) 0.43542(13) 0.51803(6) 0.0275(3) Uani 1 1 d . . . . . C13 C 0.1287(2) 0.28381(17) 0.70179(7) 0.0439(4) Uani 1 1 d . . . . . H13 H 0.117553 0.247708 0.669434 0.053 Uiso 1 1 calc R U . . . C12A C 0.26225(17) 0.49404(16) 0.47411(6) 0.0336(3) Uani 1 1 d . . . . . H12A H 0.234229 0.571474 0.468240 0.040 Uiso 1 1 calc R U . . . C14 C 0.07681(18) 0.39364(16) 0.71011(8) 0.0395(4) Uani 1 1 d . . . . . H14 H 0.028651 0.431985 0.683720 0.047 Uiso 1 1 calc R U . . . C13A C 0.3448(2) 0.43794(19) 0.43894(7) 0.0431(4) Uani 1 1 d . . . . . H13A H 0.372803 0.477545 0.408952 0.052 Uiso 1 1 calc R U . . . C15 C 0.09518(19) 0.44689(15) 0.75656(7) 0.0388(4) Uani 1 1 d . . . . . H15 H 0.060723 0.522541 0.762022 0.047 Uiso 1 1 calc R U . . . C14A C 0.3863(2) 0.32552(19) 0.44713(8) 0.0467(5) Uani 1 1 d . . . . . H14A H 0.443597 0.288533 0.423117 0.056 Uiso 1 1 calc R U . . . C16 C 0.16400(18) 0.39062(14) 0.79567(7) 0.0333(3) Uani 1 1 d . . . . . H16 H 0.177343 0.428276 0.827550 0.040 Uiso 1 1 calc R U . . . C15A C 0.3445(2) 0.26705(17) 0.49017(8) 0.0468(5) Uani 1 1 d . . . . . H15A H 0.372789 0.189561 0.495676 0.056 Uiso 1 1 calc R U . . . C16A C 0.26128(19) 0.32058(15) 0.52548(7) 0.0366(4) Uani 1 1 d . . . . . H16A H 0.231484 0.279302 0.554774 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 0.03128(19) 0.02283(17) 0.02933(18) 0.00035(14) -0.00594(15) -0.00080(15) P1A 0.02341(16) 0.02246(16) 0.02855(17) -0.00421(15) -0.00117(13) -0.00269(14) O1 0.0689(9) 0.0293(6) 0.0367(6) -0.0057(5) -0.0135(6) 0.0026(6) O2 0.0242(5) 0.0231(5) 0.0299(5) 0.0023(4) 0.0016(4) 0.0024(4) O1A 0.0365(6) 0.0321(6) 0.0428(6) -0.0063(5) 0.0075(5) -0.0110(5) O3 0.0245(5) 0.0267(5) 0.0474(7) 0.0085(5) -0.0064(5) -0.0039(4) O2A 0.0255(5) 0.0194(4) 0.0288(5) -0.0033(4) -0.0057(4) 0.0021(4) O3A 0.0277(5) 0.0267(5) 0.0363(6) -0.0059(4) -0.0119(4) 0.0005(4) C1 0.0248(6) 0.0229(6) 0.0245(6) 0.0009(5) -0.0023(5) 0.0006(6) C8A 0.0235(7) 0.0334(7) 0.0352(7) -0.0042(6) 0.0048(6) -0.0033(6) C10 0.0612(12) 0.0256(8) 0.0481(10) -0.0055(7) 0.0054(9) 0.0031(8) C2 0.0230(7) 0.0270(7) 0.0412(8) 0.0073(6) -0.0057(6) -0.0018(5) C1A 0.0206(6) 0.0183(6) 0.0250(6) -0.0006(5) -0.0019(5) 0.0014(5) C3 0.0355(9) 0.0413(10) 0.0607(11) 0.0088(9) 0.0196(8) 0.0035(7) C2A 0.0212(6) 0.0234(6) 0.0292(6) -0.0026(5) -0.0054(5) 0.0007(5) C4 0.0486(10) 0.0338(8) 0.0356(8) 0.0000(7) 0.0144(7) 0.0096(7) C3A 0.0343(8) 0.0305(8) 0.0292(7) 0.0042(6) -0.0065(6) 0.0001(6) C5 0.0357(8) 0.0251(7) 0.0334(7) -0.0001(6) 0.0041(6) 0.0049(6) C4A 0.0346(8) 0.0288(7) 0.0303(7) 0.0026(6) 0.0025(6) -0.0067(6) C6 0.0248(6) 0.0233(6) 0.0281(6) -0.0013(5) -0.0003(6) -0.0003(5) C5A 0.0290(7) 0.0214(6) 0.0335(7) -0.0009(5) -0.0026(6) -0.0031(6) C7 0.0563(10) 0.0320(8) 0.0239(7) -0.0003(6) -0.0047(6) 0.0053(8) C6A 0.0187(6) 0.0227(6) 0.0284(6) -0.0030(5) -0.0021(5) -0.0008(5) C8 0.0476(9) 0.0333(8) 0.0275(7) -0.0044(6) -0.0060(7) 0.0045(8) C7A 0.0312(7) 0.0265(7) 0.0282(7) 0.0001(5) 0.0036(6) 0.0001(6) C9 0.0416(10) 0.0364(9) 0.0537(11) 0.0054(8) -0.0072(8) 0.0118(8) C9A 0.0390(9) 0.0232(7) 0.0430(9) -0.0032(6) -0.0012(7) 0.0049(6) C11 0.0247(6) 0.0250(6) 0.0319(7) 0.0044(5) -0.0007(6) -0.0023(6) C10A 0.0404(9) 0.0319(8) 0.0555(10) -0.0063(8) -0.0037(8) -0.0129(7) C12 0.0500(10) 0.0292(8) 0.0355(8) 0.0014(6) -0.0095(7) 0.0034(7) C11A 0.0267(7) 0.0261(7) 0.0297(7) -0.0067(5) -0.0022(6) -0.0009(6) C13 0.0553(11) 0.0386(9) 0.0378(9) 0.0052(7) -0.0160(8) -0.0051(9) C12A 0.0363(8) 0.0332(7) 0.0312(7) -0.0051(6) 0.0004(6) -0.0051(7) C14 0.0312(8) 0.0378(9) 0.0494(10) 0.0190(8) -0.0076(7) -0.0046(7) C13A 0.0428(9) 0.0524(11) 0.0341(8) -0.0114(8) 0.0063(7) -0.0086(8) C15 0.0361(9) 0.0297(8) 0.0506(10) 0.0130(7) 0.0059(7) 0.0044(7) C14A 0.0401(9) 0.0556(12) 0.0442(10) -0.0228(9) 0.0041(8) 0.0036(9) C16 0.0358(8) 0.0262(7) 0.0378(8) 0.0045(6) 0.0039(6) 0.0010(6) C15A 0.0513(11) 0.0375(10) 0.0516(11) -0.0153(8) -0.0038(9) 0.0128(8) C16A 0.0447(9) 0.0286(8) 0.0365(8) -0.0051(6) -0.0030(7) 0.0038(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' 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 P1 O2 116.38(7) . . ? O1 P1 O3 116.74(8) . . ? O2 P1 O3 96.52(6) . . ? O1 P1 C11 111.68(8) . . ? O2 P1 C11 107.18(7) . . ? O3 P1 C11 106.92(7) . . ? O1A P1A O3A 116.63(7) . . ? O1A P1A O2A 115.71(7) . . ? O3A P1A O2A 97.65(6) . . ? O1A P1A C11A 111.42(7) . . ? O3A P1A C11A 107.18(7) . . ? O2A P1A C11A 107.01(6) . . ? C1 O2 P1 110.20(9) . . ? C2 O3 P1 111.86(10) . . ? C1A O2A P1A 112.52(8) . . ? C2A O3A P1A 113.92(9) . . ? O2 C1 C6 107.10(11) . . ? O2 C1 C7 106.37(12) . . ? C6 C1 C7 112.88(13) . . ? O2 C1 C2 104.75(11) . . ? C6 C1 C2 111.72(12) . . ? C7 C1 C2 113.34(13) . . ? C4A C8A C6A 86.69(11) . . ? O3 C2 C3 108.81(14) . . ? O3 C2 C1 106.47(12) . . ? C3 C2 C1 115.48(13) . . ? O2A C1A C6A 106.64(11) . . ? O2A C1A C7A 106.11(11) . . ? C6A C1A C7A 112.83(12) . . ? O2A C1A C2A 105.16(11) . . ? C6A C1A C2A 112.13(11) . . ? C7A C1A C2A 113.24(12) . . ? C4 C3 C2 113.21(14) . . ? O3A C2A C3A 109.31(12) . . ? O3A C2A C1A 106.76(11) . . ? C3A C2A C1A 115.13(12) . . ? C3 C4 C8 108.72(15) . . ? C3 C4 C5 111.03(16) . . ? C8 C4 C5 88.06(13) . . ? C4A C3A C2A 113.44(12) . . ? C9 C5 C10 108.22(15) . . ? C9 C5 C4 117.98(16) . . ? C10 C5 C4 112.05(14) . . ? C9 C5 C6 121.81(14) . . ? C10 C5 C6 109.83(14) . . ? C4 C5 C6 85.40(12) . . ? C3A C4A C8A 108.97(12) . . ? C3A C4A C5A 110.92(13) . . ? C8A C4A C5A 87.79(12) . . ? C1 C6 C8 109.03(12) . . ? C1 C6 C5 112.37(12) . . ? C8 C6 C5 87.03(12) . . ? C9A C5A C10A 107.97(13) . . ? C9A C5A C4A 118.33(14) . . ? C10A C5A C4A 112.09(14) . . ? C9A C5A C6A 121.81(13) . . ? C10A C5A C6A 109.90(13) . . ? C4A C5A C6A 85.23(11) . . ? C1A C6A C8A 108.86(11) . . ? C1A C6A C5A 112.98(12) . . ? C8A C6A C5A 87.15(11) . . ? C4 C8 C6 86.83(13) . . ? C16 C11 C12 119.37(15) . . ? C16 C11 P1 117.88(12) . . ? C12 C11 P1 122.71(12) . . ? C13 C12 C11 120.00(17) . . ? C12A C11A C16A 119.46(15) . . ? C12A C11A P1A 122.32(12) . . ? C16A C11A P1A 118.22(13) . . ? C14 C13 C12 120.22(18) . . ? C13A C12A C11A 119.37(17) . . ? C15 C14 C13 119.94(16) . . ? C14A C13A C12A 120.80(18) . . ? C14 C15 C16 120.38(16) . . ? C15A C14A C13A 119.90(17) . . ? C11 C16 C15 120.06(17) . . ? C14A C15A C16A 120.40(18) . . ? C15A C16A C11A 120.05(17) . . ? 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 O1 1.4664(12) . ? P1 O2 1.5887(11) . ? P1 O3 1.5920(13) . ? P1 C11 1.7798(15) . ? P1A O1A 1.4666(12) . ? P1A O3A 1.5846(12) . ? P1A O2A 1.5931(10) . ? P1A C11A 1.7804(15) . ? O2 C1 1.4763(17) . ? O3 C2 1.4627(18) . ? O2A C1A 1.4776(16) . ? O3A C2A 1.4589(17) . ? C1 C6 1.515(2) . ? C1 C7 1.522(2) . ? C1 C2 1.568(2) . ? C8A C4A 1.543(2) . ? C8A C6A 1.548(2) . ? C10 C5 1.533(2) . ? C2 C3 1.543(3) . ? C1A C6A 1.5141(19) . ? C1A C7A 1.516(2) . ? C1A C2A 1.5680(19) . ? C3 C4 1.518(3) . ? C2A C3A 1.543(2) . ? C4 C8 1.539(3) . ? C4 C5 1.553(2) . ? C3A C4A 1.527(2) . ? C5 C9 1.523(2) . ? C5 C6 1.574(2) . ? C4A C5A 1.560(2) . ? C6 C8 1.547(2) . ? C5A C9A 1.521(2) . ? C5A C10A 1.529(2) . ? C5A C6A 1.573(2) . ? C11 C16 1.391(2) . ? C11 C12 1.394(2) . ? C12 C13 1.389(2) . ? C11A C12A 1.395(2) . ? C11A C16A 1.400(2) . ? C13 C14 1.388(3) . ? C12A C13A 1.393(2) . ? C14 C15 1.374(3) . ? C13A C14A 1.380(3) . ? C15 C16 1.392(2) . ? C14A C15A 1.377(3) . ? C15A C16A 1.386(3) . ?