#------------------------------------------------------------------------------ #$Date: 2023-11-25 04:09:24 +0200 (Sat, 25 Nov 2023) $ #$Revision: 287798 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247792.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_7247792 loop_ _publ_author_name 'Ramazanova, Kyzgaldak' 'Chakrabortty, Soumyadeep' 'M\"uller, Bernd H.' 'L\"onnecke, Peter' 'de Vries, Johannes G.' 'Hey-Hawkins, Evamarie' _publ_section_title ; Synthesis of P-stereogenic 1-phosphanorbornane-derived phosphine--phosphite ligands and application in asymmetric catalysis ; _journal_issue 49 _journal_name_full 'RSC Advances' _journal_page_first 34439 _journal_page_last 34444 _journal_paper_doi 10.1039/D3RA07630J _journal_volume 13 _journal_year 2023 _chemical_absolute_configuration rmad _chemical_formula_moiety 'C30 H28 O4 P2 S2' _chemical_formula_sum 'C30 H28 O4 P2 S2' _chemical_formula_weight 578.58 _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 difmap _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2023-10-19 deposited with the CCDC. 2023-11-10 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.43040(10) _cell_length_b 16.7705(3) _cell_length_c 22.5342(3) _cell_measurement_reflns_used 14382 _cell_measurement_temperature 130(2) _cell_measurement_theta_max 27.2710 _cell_measurement_theta_min 2.5690 _cell_volume 2808.02(7) _computing_cell_refinement 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)' _computing_molecular_graphics ; ORTEP3 for Windows L. J. Farrugia, J. Appl. Crystallogr. 1997, 30, 565. or DIAMOND Version 4.6.8 K. Brandenburg, Crystal Impact GbR, Bonn, Germany ; _computing_publication_material ; WINGX L.J. Farrugia, J. Appl. Cryst., 2012, 45, 849-854. ; _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution SHELXT-2018-2 _diffrn_ambient_temperature 130(2) _diffrn_detector_area_resol_mean 16.3560 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.953 _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0619 _diffrn_reflns_av_unetI/netI 0.0420 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.953 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 39714 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.933 _diffrn_reflns_theta_full 25.350 _diffrn_reflns_theta_max 27.712 _diffrn_reflns_theta_min 2.178 _diffrn_source 'fine-focus sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.339 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.88899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_density_diffrn 1.369 _exptl_crystal_description irregular _exptl_crystal_F_000 1208 _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _refine_diff_density_max 0.298 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.047 _refine_ls_abs_structure_details ; Flack x determined using 2058 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.02(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 455 _refine_ls_number_reflns 6143 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0458 _refine_ls_R_factor_gt 0.0360 _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^)+(0.0337P)^2^+0.7984P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0765 _refine_ls_wR_factor_ref 0.0813 _reflns_Friedel_coverage 0.729 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.906 _reflns_number_gt 5439 _reflns_number_total 6143 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra07630j2.cif _cod_data_source_block comp9b_x3698fin _cod_database_code 7247792 _shelx_shelxl_version_number 2018/3 _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_res_file ; TITL x3698fin in P2(1)2(1)2(1) comp9b_x3698fin.res created by SHELXL-2018/3 at 17:14:58 on 19-Oct-2023 CELL 0.71073 7.4304 16.7705 22.5342 90.000 90.000 90.000 ZERR 4.00 0.0001 0.0003 0.0003 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 S P O C H UNIT 8 8 16 120 112 MERG 2 FMAP 2 PLAN 5 ACTA 50.70 BOND $H L.S. 10 TEMP -143.00 WGHT 0.033700 0.798400 FVAR 0.20215 S1 1 0.737678 0.166663 0.976524 11.00000 0.03659 0.04080 = 0.02728 0.00140 0.00014 0.00862 S2 1 0.342193 0.075664 0.802897 11.00000 0.03844 0.03038 = 0.03753 0.00592 0.00237 0.00206 P1 2 0.758430 0.260500 0.926626 11.00000 0.02006 0.03317 = 0.02391 -0.00577 -0.00037 0.00329 P2 2 0.281188 0.176964 0.772235 11.00000 0.02110 0.02849 = 0.02419 0.00089 -0.00027 -0.00155 O1 3 0.611049 0.442769 0.874020 11.00000 0.03539 0.03339 = 0.05750 -0.00771 -0.00070 0.00732 O2 3 0.348315 0.252683 0.806306 11.00000 0.02732 0.03145 = 0.02843 0.00194 -0.00630 -0.00371 O3 3 0.072304 0.199099 0.768492 11.00000 0.01924 0.03375 = 0.02176 -0.00362 0.00133 -0.00241 O4 3 0.348404 0.189402 0.705969 11.00000 0.01978 0.03335 = 0.02737 0.00234 0.00206 0.00185 C1 4 0.877312 0.364412 0.858238 11.00000 0.02178 0.03322 = 0.03615 -0.00690 0.00338 -0.00313 C2 4 0.770152 0.415490 0.904633 11.00000 0.02886 0.02840 = 0.04592 -0.00985 -0.00062 -0.00280 C3 4 0.711270 0.358861 0.955653 11.00000 0.02442 0.03900 = 0.03654 -0.01540 0.00419 -0.00070 C4 4 0.638352 0.258766 0.855870 11.00000 0.02076 0.02389 = 0.02563 -0.00368 -0.00113 0.00150 C5 4 0.716382 0.331377 0.821544 11.00000 0.02467 0.03108 = 0.02584 -0.00178 0.00022 -0.00077 C6 4 0.594177 0.403619 0.817992 11.00000 0.03391 0.02736 = 0.04195 0.00473 -0.00364 -0.00010 C7 4 0.962283 0.294547 0.891506 11.00000 0.01705 0.04501 = 0.03290 -0.01072 0.00164 0.00201 C8 4 1.009749 0.411068 0.820245 11.00000 0.03360 0.04368 = 0.05411 -0.00312 0.00877 -0.00811 C9 4 0.868149 0.487932 0.929314 11.00000 0.04841 0.04105 = 0.06983 -0.02083 0.00611 -0.01177 C10 4 0.436356 0.253691 0.863910 11.00000 0.02033 0.03558 = 0.02546 -0.00025 -0.00388 -0.00139 C11 4 -0.031433 0.174630 0.719653 11.00000 0.01837 0.02532 = 0.02141 -0.00486 0.00058 0.00107 C12 4 -0.004020 0.209805 0.665743 11.00000 0.01824 0.02206 = 0.02583 -0.00204 0.00223 0.00127 C13 4 -0.107766 0.181465 0.616693 11.00000 0.01960 0.02404 = 0.02565 -0.00168 0.00015 0.00284 C14 4 -0.072753 0.205404 0.557400 11.00000 0.02780 0.02759 = 0.02774 0.00119 -0.00096 -0.00077 C15 4 -0.174777 0.176650 0.512172 11.00000 0.04164 0.03725 = 0.02521 0.00041 -0.00301 -0.00375 C16 4 -0.316797 0.123559 0.522995 11.00000 0.04606 0.04367 = 0.03169 -0.00359 -0.01471 -0.01105 C17 4 -0.351489 0.098127 0.578970 11.00000 0.03030 0.03594 = 0.03946 -0.00050 -0.00743 -0.01057 C18 4 -0.246065 0.124692 0.627341 11.00000 0.02141 0.02540 = 0.02972 -0.00258 -0.00269 -0.00109 C19 4 -0.272935 0.095220 0.685326 11.00000 0.02342 0.02169 = 0.03425 0.00041 0.00274 -0.00387 C20 4 -0.165047 0.117595 0.730374 11.00000 0.02308 0.02441 = 0.02460 0.00222 0.00390 0.00194 C21 4 0.303361 0.262915 0.679180 11.00000 0.02500 0.03169 = 0.02121 0.00118 0.00008 -0.00388 C22 4 0.131979 0.274882 0.659820 11.00000 0.02255 0.02687 = 0.02036 -0.00255 0.00352 -0.00449 C23 4 0.087372 0.352422 0.637493 11.00000 0.02906 0.02854 = 0.02018 -0.00350 0.00556 -0.00326 C24 4 -0.088625 0.374359 0.619951 11.00000 0.02859 0.02510 = 0.03120 -0.00130 0.00531 -0.00034 C25 4 -0.124407 0.449573 0.599899 11.00000 0.03603 0.03372 = 0.03913 0.00111 0.01384 0.00639 C26 4 0.010794 0.507486 0.596539 11.00000 0.05475 0.02309 = 0.04180 0.00192 0.01689 0.00284 C27 4 0.181554 0.488472 0.613543 11.00000 0.04507 0.02722 = 0.04150 -0.00191 0.01199 -0.00984 C28 4 0.224824 0.411629 0.634648 11.00000 0.03643 0.02753 = 0.02498 -0.00033 0.00490 -0.00853 C29 4 0.401440 0.392003 0.652493 11.00000 0.03365 0.04376 = 0.03217 0.00490 0.00138 -0.02095 C30 4 0.440743 0.319445 0.674963 11.00000 0.02202 0.04864 = 0.02734 0.00268 -0.00097 -0.01106 H3A 5 0.797864 0.371222 0.988107 11.00000 0.03229 H3B 5 0.592916 0.367497 0.964934 11.00000 0.04273 H4 5 0.681259 0.209301 0.836763 11.00000 0.03287 H5 5 0.753094 0.316376 0.781579 11.00000 0.02002 H6A 5 0.629928 0.434953 0.789765 11.00000 0.03812 H6B 5 0.475737 0.391004 0.809809 11.00000 0.02860 H7A 5 1.055154 0.311943 0.920509 11.00000 0.04619 H7B 5 1.010909 0.254249 0.867996 11.00000 0.02402 H8A 5 1.064801 0.374480 0.789995 11.00000 0.05416 H8B 5 0.961134 0.453410 0.799685 11.00000 0.02074 H8C 5 1.099784 0.424538 0.852436 11.00000 0.03461 H9A 5 0.800993 0.510778 0.959844 11.00000 0.05466 H9B 5 0.885323 0.521597 0.897208 11.00000 0.05046 H9C 5 0.994645 0.473631 0.946250 11.00000 0.02787 H10A 5 0.406638 0.201769 0.886439 11.00000 0.02862 H10B 5 0.387841 0.298405 0.882214 11.00000 0.02866 H14 5 0.027831 0.238640 0.550321 11.00000 0.02534 H15 5 -0.138059 0.191654 0.473079 11.00000 0.04631 H16 5 -0.384129 0.106170 0.490638 11.00000 0.03220 H17 5 -0.440376 0.064842 0.585611 11.00000 0.03582 H19 5 -0.365453 0.058012 0.689742 11.00000 0.02855 H20 5 -0.175988 0.098352 0.766795 11.00000 0.02088 H24 5 -0.182409 0.335158 0.622349 11.00000 0.02468 H25 5 -0.249922 0.459798 0.588194 11.00000 0.03523 H26 5 -0.017146 0.557563 0.581740 11.00000 0.04472 H27 5 0.271735 0.522618 0.613876 11.00000 0.04576 H29 5 0.485606 0.428791 0.647892 11.00000 0.04869 H30 5 0.537505 0.310575 0.689183 11.00000 0.03773 HKLF 4 REM x3698fin in P2(1)2(1)2(1) REM wR2 = 0.0813, GooF = S = 1.031, Restrained GooF = 1.031 for all data REM R1 = 0.0360 for 5439 Fo > 4sig(Fo) and 0.0458 for all 6143 data REM 455 parameters refined using 0 restraints END WGHT 0.0337 0.7806 REM Highest difference peak 0.298, deepest hole -0.259, 1-sigma level 0.047 Q1 1 0.3187 0.1224 0.7812 11.00000 0.05 0.30 Q2 1 0.7372 0.3223 0.9327 11.00000 0.05 0.25 Q3 1 0.3179 0.1380 0.8110 11.00000 0.05 0.23 Q4 1 0.7478 0.1947 0.9304 11.00000 0.05 0.22 Q5 1 0.0950 0.3195 0.6634 11.00000 0.05 0.21 ; _shelx_res_checksum 57851 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 S1 S 0.73768(13) 0.16666(5) 0.97652(4) 0.0349(2) Uani 1 1 d . . . . . S2 S 0.34219(13) 0.07566(5) 0.80290(4) 0.0354(2) Uani 1 1 d . . . . . P1 P 0.75843(11) 0.26050(5) 0.92663(3) 0.02571(18) Uani 1 1 d . . . . . P2 P 0.28119(10) 0.17696(5) 0.77223(3) 0.02460(18) Uani 1 1 d . . . . . O1 O 0.6110(3) 0.44277(14) 0.87402(12) 0.0421(6) Uani 1 1 d . . . . . O2 O 0.3483(3) 0.25268(13) 0.80631(10) 0.0291(5) Uani 1 1 d . . . . . O3 O 0.0723(3) 0.19910(13) 0.76849(9) 0.0249(5) Uani 1 1 d . . . . . O4 O 0.3484(3) 0.18940(13) 0.70597(9) 0.0268(5) Uani 1 1 d . . . . . C1 C 0.8773(4) 0.36441(19) 0.85824(15) 0.0304(7) Uani 1 1 d . . . . . C2 C 0.7702(5) 0.41549(19) 0.90463(16) 0.0344(8) Uani 1 1 d . . . . . C3 C 0.7113(5) 0.3589(2) 0.95565(16) 0.0333(8) Uani 1 1 d . . . . . C4 C 0.6384(4) 0.25877(18) 0.85587(13) 0.0234(6) Uani 1 1 d . . . . . C5 C 0.7164(4) 0.33138(19) 0.82154(14) 0.0272(7) Uani 1 1 d . . . . . C6 C 0.5942(5) 0.4036(2) 0.81799(18) 0.0344(8) Uani 1 1 d . . . . . C7 C 0.9623(4) 0.2945(2) 0.89151(16) 0.0317(8) Uani 1 1 d . . . . . C8 C 1.0097(6) 0.4111(3) 0.8202(2) 0.0438(10) Uani 1 1 d . . . . . C9 C 0.8681(7) 0.4879(3) 0.9293(3) 0.0531(11) Uani 1 1 d . . . . . C10 C 0.4364(4) 0.2537(2) 0.86391(14) 0.0271(7) Uani 1 1 d . . . . . C11 C -0.0314(4) 0.17463(18) 0.71965(13) 0.0217(6) Uani 1 1 d . . . . . C12 C -0.0040(4) 0.20981(17) 0.66574(14) 0.0220(6) Uani 1 1 d . . . . . C13 C -0.1078(4) 0.18146(18) 0.61669(13) 0.0231(6) Uani 1 1 d . . . . . C14 C -0.0728(5) 0.20540(19) 0.55740(14) 0.0277(7) Uani 1 1 d . . . . . C15 C -0.1748(5) 0.1767(2) 0.51217(15) 0.0347(8) Uani 1 1 d . . . . . C16 C -0.3168(6) 0.1236(2) 0.52300(17) 0.0405(9) Uani 1 1 d . . . . . C17 C -0.3515(5) 0.0981(2) 0.57897(16) 0.0352(8) Uani 1 1 d . . . . . C18 C -0.2461(4) 0.12469(17) 0.62734(13) 0.0255(6) Uani 1 1 d . . . . . C19 C -0.2729(4) 0.09522(18) 0.68533(14) 0.0265(7) Uani 1 1 d . . . . . C20 C -0.1650(4) 0.11759(18) 0.73037(14) 0.0240(6) Uani 1 1 d . . . . . C21 C 0.3034(4) 0.26291(19) 0.67918(13) 0.0260(7) Uani 1 1 d . . . . . C22 C 0.1320(4) 0.27488(18) 0.65982(13) 0.0233(7) Uani 1 1 d . . . . . C23 C 0.0874(4) 0.35242(19) 0.63749(14) 0.0259(7) Uani 1 1 d . . . . . C24 C -0.0886(5) 0.37436(19) 0.61995(15) 0.0283(7) Uani 1 1 d . . . . . C25 C -0.1244(5) 0.4496(2) 0.59990(17) 0.0363(9) Uani 1 1 d . . . . . C26 C 0.0108(6) 0.5075(2) 0.59654(17) 0.0399(9) Uani 1 1 d . . . . . C27 C 0.1816(6) 0.4885(2) 0.61354(17) 0.0379(9) Uani 1 1 d . . . . . C28 C 0.2248(5) 0.41163(18) 0.63465(14) 0.0296(7) Uani 1 1 d . . . . . C29 C 0.4014(5) 0.3920(2) 0.65249(16) 0.0365(9) Uani 1 1 d . . . . . C30 C 0.4407(5) 0.3194(2) 0.67496(15) 0.0327(8) Uani 1 1 d . . . . . H3A H 0.798(5) 0.371(2) 0.9881(15) 0.032(9) Uiso 1 1 d . . . . . H3B H 0.593(6) 0.367(2) 0.9649(16) 0.043(11) Uiso 1 1 d . . . . . H4 H 0.681(5) 0.209(2) 0.8368(15) 0.033(9) Uiso 1 1 d . . . . . H5 H 0.753(4) 0.3164(17) 0.7816(14) 0.020(7) Uiso 1 1 d . . . . . H6A H 0.630(5) 0.435(2) 0.7898(17) 0.038(11) Uiso 1 1 d . . . . . H6B H 0.476(5) 0.391(2) 0.8098(15) 0.029(9) Uiso 1 1 d . . . . . H7A H 1.055(5) 0.312(2) 0.9205(17) 0.046(11) Uiso 1 1 d . . . . . H7B H 1.011(4) 0.254(2) 0.8680(14) 0.024(8) Uiso 1 1 d . . . . . H8A H 1.065(6) 0.374(3) 0.7900(19) 0.054(12) Uiso 1 1 d . . . . . H8B H 0.961(5) 0.453(2) 0.7997(15) 0.021(9) Uiso 1 1 d . . . . . H8C H 1.100(5) 0.425(2) 0.8524(16) 0.035(10) Uiso 1 1 d . . . . . H9A H 0.801(6) 0.511(2) 0.960(2) 0.055(13) Uiso 1 1 d . . . . . H9B H 0.885(6) 0.522(3) 0.8972(19) 0.050(13) Uiso 1 1 d . . . . . H9C H 0.995(5) 0.4736(19) 0.9462(15) 0.028(9) Uiso 1 1 d . . . . . H10A H 0.407(5) 0.202(2) 0.8864(15) 0.029(9) Uiso 1 1 d . . . . . H10B H 0.388(5) 0.298(2) 0.8822(15) 0.029(9) Uiso 1 1 d . . . . . H14 H 0.028(5) 0.2386(19) 0.5503(14) 0.025(9) Uiso 1 1 d . . . . . H15 H -0.138(5) 0.192(2) 0.4731(17) 0.046(11) Uiso 1 1 d . . . . . H16 H -0.384(5) 0.106(2) 0.4906(15) 0.032(9) Uiso 1 1 d . . . . . H17 H -0.440(5) 0.065(2) 0.5856(16) 0.036(10) Uiso 1 1 d . . . . . H19 H -0.365(5) 0.058(2) 0.6897(14) 0.029(9) Uiso 1 1 d . . . . . H20 H -0.176(4) 0.0984(18) 0.7668(14) 0.021(8) Uiso 1 1 d . . . . . H24 H -0.182(4) 0.3352(19) 0.6223(14) 0.025(8) Uiso 1 1 d . . . . . H25 H -0.250(6) 0.460(2) 0.5882(15) 0.035(10) Uiso 1 1 d . . . . . H26 H -0.017(5) 0.558(2) 0.5817(17) 0.045(11) Uiso 1 1 d . . . . . H27 H 0.272(6) 0.523(2) 0.6139(17) 0.046(11) Uiso 1 1 d . . . . . H29 H 0.486(6) 0.429(2) 0.6479(17) 0.049(12) Uiso 1 1 d . . . . . H30 H 0.538(6) 0.311(2) 0.6892(16) 0.038(11) Uiso 1 1 d . . . . . 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 S1 0.0366(5) 0.0408(5) 0.0273(4) 0.0014(3) 0.0001(4) 0.0086(4) S2 0.0384(5) 0.0304(4) 0.0375(5) 0.0059(4) 0.0024(4) 0.0021(4) P1 0.0201(4) 0.0332(4) 0.0239(4) -0.0058(3) -0.0004(3) 0.0033(4) P2 0.0211(4) 0.0285(4) 0.0242(4) 0.0009(3) -0.0003(3) -0.0016(3) O1 0.0354(14) 0.0334(13) 0.0575(17) -0.0077(12) -0.0007(13) 0.0073(11) O2 0.0273(11) 0.0315(12) 0.0284(12) 0.0019(10) -0.0063(10) -0.0037(10) O3 0.0192(10) 0.0337(12) 0.0218(11) -0.0036(9) 0.0013(9) -0.0024(9) O4 0.0198(10) 0.0334(12) 0.0274(12) 0.0023(9) 0.0021(9) 0.0018(9) C1 0.0218(16) 0.0332(18) 0.0362(19) -0.0069(14) 0.0034(14) -0.0031(14) C2 0.0289(18) 0.0284(17) 0.046(2) -0.0099(14) -0.0006(16) -0.0028(15) C3 0.0244(18) 0.0390(19) 0.0365(19) -0.0154(15) 0.0042(15) -0.0007(15) C4 0.0208(15) 0.0239(15) 0.0256(16) -0.0037(13) -0.0011(12) 0.0015(13) C5 0.0247(16) 0.0311(16) 0.0258(16) -0.0018(13) 0.0002(13) -0.0008(14) C6 0.034(2) 0.0274(18) 0.042(2) 0.0047(16) -0.0036(17) -0.0001(15) C7 0.0170(15) 0.045(2) 0.0329(19) -0.0107(16) 0.0016(14) 0.0020(14) C8 0.034(2) 0.044(2) 0.054(3) -0.003(2) 0.009(2) -0.0081(18) C9 0.048(3) 0.041(2) 0.070(3) -0.021(2) 0.006(3) -0.012(2) C10 0.0203(15) 0.0356(19) 0.0255(17) -0.0003(15) -0.0039(13) -0.0014(14) C11 0.0184(13) 0.0253(15) 0.0214(15) -0.0049(12) 0.0006(12) 0.0011(12) C12 0.0182(14) 0.0221(15) 0.0258(16) -0.0020(12) 0.0022(12) 0.0013(12) C13 0.0196(14) 0.0240(15) 0.0256(16) -0.0017(12) 0.0001(12) 0.0028(12) C14 0.0278(17) 0.0276(17) 0.0277(18) 0.0012(13) -0.0010(14) -0.0008(14) C15 0.0416(19) 0.0372(19) 0.0252(18) 0.0004(14) -0.0030(15) -0.0037(17) C16 0.046(2) 0.044(2) 0.0317(19) -0.0036(16) -0.0147(18) -0.0111(17) C17 0.0303(18) 0.0359(19) 0.039(2) -0.0005(15) -0.0074(16) -0.0106(16) C18 0.0214(15) 0.0254(14) 0.0297(16) -0.0026(12) -0.0027(14) -0.0011(13) C19 0.0234(16) 0.0217(15) 0.0343(17) 0.0004(12) 0.0027(14) -0.0039(13) C20 0.0231(15) 0.0244(15) 0.0246(17) 0.0022(13) 0.0039(14) 0.0019(13) C21 0.0250(15) 0.0317(16) 0.0212(15) 0.0012(12) 0.0001(13) -0.0039(13) C22 0.0226(15) 0.0269(16) 0.0204(15) -0.0025(12) 0.0035(12) -0.0045(13) C23 0.0291(16) 0.0285(17) 0.0202(16) -0.0035(13) 0.0056(13) -0.0033(13) C24 0.0286(17) 0.0251(16) 0.0312(18) -0.0013(13) 0.0053(14) -0.0003(14) C25 0.036(2) 0.0337(19) 0.039(2) 0.0011(15) 0.0138(17) 0.0064(16) C26 0.055(3) 0.0231(19) 0.042(2) 0.0019(15) 0.0169(19) 0.0028(17) C27 0.045(2) 0.0272(18) 0.042(2) -0.0019(15) 0.0120(18) -0.0098(17) C28 0.0364(19) 0.0275(16) 0.0250(15) -0.0003(12) 0.0049(15) -0.0085(14) C29 0.0336(19) 0.044(2) 0.032(2) 0.0049(16) 0.0014(16) -0.0209(17) C30 0.0220(17) 0.049(2) 0.0273(19) 0.0027(16) -0.0010(14) -0.0111(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' 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 C7 P1 C3 91.87(17) . . ? C7 P1 C4 91.85(15) . . ? C3 P1 C4 103.62(16) . . ? C7 P1 S1 125.33(13) . . ? C3 P1 S1 120.98(13) . . ? C4 P1 S1 117.00(11) . . ? O2 P2 O4 104.74(12) . . ? O2 P2 O3 98.45(12) . . ? O4 P2 O3 103.02(11) . . ? O2 P2 S2 118.27(9) . . ? O4 P2 S2 112.74(9) . . ? O3 P2 S2 117.47(9) . . ? C6 O1 C2 110.4(3) . . ? C10 O2 P2 126.2(2) . . ? C11 O3 P2 120.42(18) . . ? C21 O4 P2 116.22(19) . . ? C8 C1 C7 113.8(3) . . ? C8 C1 C5 112.4(3) . . ? C7 C1 C5 107.8(3) . . ? C8 C1 C2 115.0(3) . . ? C7 C1 C2 107.6(3) . . ? C5 C1 C2 99.1(3) . . ? O1 C2 C9 108.3(3) . . ? O1 C2 C3 108.5(3) . . ? C9 C2 C3 110.6(3) . . ? O1 C2 C1 105.7(3) . . ? C9 C2 C1 115.9(3) . . ? C3 C2 C1 107.6(3) . . ? C2 C3 P1 103.6(2) . . ? C2 C3 H3A 104(2) . . ? P1 C3 H3A 109(2) . . ? C2 C3 H3B 110(2) . . ? P1 C3 H3B 114(2) . . ? H3A C3 H3B 115(3) . . ? C10 C4 C5 118.2(3) . . ? C10 C4 P1 112.4(2) . . ? C5 C4 P1 103.9(2) . . ? C10 C4 H4 109(2) . . ? C5 C4 H4 109(2) . . ? P1 C4 H4 104(2) . . ? C6 C5 C4 115.4(3) . . ? C6 C5 C1 101.8(3) . . ? C4 C5 C1 107.5(3) . . ? C6 C5 H5 109.0(18) . . ? C4 C5 H5 111.2(17) . . ? C1 C5 H5 111.6(19) . . ? O1 C6 C5 105.5(3) . . ? O1 C6 H6A 110(2) . . ? C5 C6 H6A 110(3) . . ? O1 C6 H6B 111(2) . . ? C5 C6 H6B 113(2) . . ? H6A C6 H6B 107(3) . . ? C1 C7 P1 96.4(2) . . ? C1 C7 H7A 113(2) . . ? P1 C7 H7A 113(2) . . ? C1 C7 H7B 116(2) . . ? P1 C7 H7B 110(2) . . ? H7A C7 H7B 109(3) . . ? C1 C8 H8A 109(3) . . ? C1 C8 H8B 115(2) . . ? H8A C8 H8B 107(3) . . ? C1 C8 H8C 98(2) . . ? H8A C8 H8C 111(3) . . ? H8B C8 H8C 117(3) . . ? C2 C9 H9A 110(3) . . ? C2 C9 H9B 105(3) . . ? H9A C9 H9B 114(4) . . ? C2 C9 H9C 112.4(19) . . ? H9A C9 H9C 108(3) . . ? H9B C9 H9C 108(4) . . ? O2 C10 C4 109.9(3) . . ? O2 C10 H10A 109.5(19) . . ? C4 C10 H10A 109(2) . . ? O2 C10 H10B 103(2) . . ? C4 C10 H10B 113(2) . . ? H10A C10 H10B 112(3) . . ? C12 C11 C20 123.7(3) . . ? C12 C11 O3 119.3(3) . . ? C20 C11 O3 117.0(3) . . ? C11 C12 C13 117.6(3) . . ? C11 C12 C22 119.7(3) . . ? C13 C12 C22 122.6(3) . . ? C14 C13 C18 118.8(3) . . ? C14 C13 C12 122.4(3) . . ? C18 C13 C12 118.8(3) . . ? C15 C14 C13 120.2(3) . . ? C15 C14 H14 122(2) . . ? C13 C14 H14 118(2) . . ? C14 C15 C16 121.0(3) . . ? C14 C15 H15 116(2) . . ? C16 C15 H15 123(2) . . ? C17 C16 C15 120.3(3) . . ? C17 C16 H16 122(2) . . ? C15 C16 H16 118(2) . . ? C16 C17 C18 120.8(3) . . ? C16 C17 H17 120(2) . . ? C18 C17 H17 119(2) . . ? C19 C18 C17 121.7(3) . . ? C19 C18 C13 119.6(3) . . ? C17 C18 C13 118.8(3) . . ? C20 C19 C18 121.1(3) . . ? C20 C19 H19 123(2) . . ? C18 C19 H19 116(2) . . ? C19 C20 C11 118.9(3) . . ? C19 C20 H20 123(2) . . ? C11 C20 H20 118(2) . . ? C22 C21 C30 124.2(3) . . ? C22 C21 O4 119.2(3) . . ? C30 C21 O4 116.6(3) . . ? C21 C22 C23 117.6(3) . . ? C21 C22 C12 119.8(3) . . ? C23 C22 C12 122.5(3) . . ? C24 C23 C28 117.9(3) . . ? C24 C23 C22 123.2(3) . . ? C28 C23 C22 118.8(3) . . ? C25 C24 C23 120.8(3) . . ? C25 C24 H24 120.7(19) . . ? C23 C24 H24 118.5(19) . . ? C24 C25 C26 121.3(4) . . ? C24 C25 H25 116(2) . . ? C26 C25 H25 123(2) . . ? C27 C26 C25 119.4(4) . . ? C27 C26 H26 121(3) . . ? C25 C26 H26 119(3) . . ? C26 C27 C28 121.4(4) . . ? C26 C27 H27 124(3) . . ? C28 C27 H27 115(3) . . ? C27 C28 C29 121.4(3) . . ? C27 C28 C23 119.2(3) . . ? C29 C28 C23 119.4(3) . . ? C30 C29 C28 121.2(3) . . ? C30 C29 H29 121(3) . . ? C28 C29 H29 117(3) . . ? C29 C30 C21 118.6(3) . . ? C29 C30 H30 121(3) . . ? C21 C30 H30 120(3) . . ? 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 S1 P1 1.9403(12) . ? S2 P2 1.8892(12) . ? P1 C7 1.802(4) . ? P1 C3 1.809(3) . ? P1 C4 1.827(3) . ? P2 O2 1.565(2) . ? P2 O4 1.588(2) . ? P2 O3 1.598(2) . ? O1 C6 1.429(5) . ? O1 C2 1.443(4) . ? O2 C10 1.454(4) . ? O3 C11 1.405(3) . ? O4 C21 1.413(4) . ? C1 C8 1.521(5) . ? C1 C7 1.528(5) . ? C1 C5 1.556(5) . ? C1 C2 1.569(5) . ? C2 C9 1.522(5) . ? C2 C3 1.554(5) . ? C3 H3A 1.00(4) . ? C3 H3B 0.92(4) . ? C4 C10 1.514(4) . ? C4 C5 1.555(4) . ? C4 H4 0.99(3) . ? C5 C6 1.516(5) . ? C5 H5 0.97(3) . ? C6 H6A 0.87(4) . ? C6 H6B 0.92(4) . ? C7 H7A 0.99(4) . ? C7 H7B 0.93(3) . ? C8 H8A 1.00(4) . ? C8 H8B 0.92(3) . ? C8 H8C 1.01(4) . ? C9 H9A 0.93(5) . ? C9 H9B 0.93(4) . ? C9 H9C 1.04(4) . ? C10 H10A 1.03(3) . ? C10 H10B 0.93(4) . ? C11 C12 1.366(4) . ? C11 C20 1.400(4) . ? C12 C13 1.429(4) . ? C12 C22 1.493(4) . ? C13 C14 1.419(4) . ? C13 C18 1.421(4) . ? C14 C15 1.359(5) . ? C14 H14 0.95(3) . ? C15 C16 1.402(5) . ? C15 H15 0.96(4) . ? C16 C17 1.356(5) . ? C16 H16 0.93(4) . ? C17 C18 1.414(5) . ? C17 H17 0.88(4) . ? C18 C19 1.411(4) . ? C19 C20 1.347(4) . ? C19 H19 0.93(4) . ? C20 H20 0.89(3) . ? C21 C22 1.361(4) . ? C21 C30 1.396(5) . ? C22 C23 1.433(4) . ? C23 C24 1.415(5) . ? C23 C28 1.426(4) . ? C24 C25 1.366(5) . ? C24 H24 0.96(3) . ? C25 C26 1.399(6) . ? C25 H25 0.98(4) . ? C26 C27 1.363(6) . ? C26 H26 0.93(4) . ? C27 C28 1.411(5) . ? C27 H27 0.88(4) . ? C28 C29 1.411(5) . ? C29 C30 1.350(6) . ? C29 H29 0.88(4) . ? C30 H30 0.80(4) . ?