#------------------------------------------------------------------------------ #$Date: 2020-10-06 11:55:17 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257546 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/53/7705332.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_7705332 loop_ _publ_author_name 'Begum, Imtiaz' 'Kalisch, Tim' 'Schnakenburg, Gregor' 'Kelemen, Zsolt' 'Nyul\'aszi, L\'aszl\'o' 'Streubel, Rainer' _publ_section_title ; [4 + 2]-Cycloadditions of a thiazol-based tricyclic 1,4-diphosphinine and a new easy 1,4-diphosphinine protection deprotection strategy. ; _journal_issue 36 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 12776 _journal_page_last 12779 _journal_paper_doi 10.1039/d0dt02529a _journal_volume 49 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_moiety 'C22 H21 N3 O2 P2 S4' _chemical_formula_sum 'C22 H21 N3 O2 P2 S4' _chemical_formula_weight 549.60 _chemical_name_systematic IB-305 _space_group_crystal_system orthorhombic _space_group_IT_number 33 _space_group_name_Hall 'P 2c -2n' _space_group_name_H-M_alt 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2018-09-12 _audit_creation_method ; Olex2 1.2 (compiled 2018.04.18 svn.r3501 for OlexSys, GUI svn.r5488) ; _audit_update_record ; 2019-07-18 deposited with the CCDC. 2020-08-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 15.3334(4) _cell_length_b 11.3840(3) _cell_length_c 27.2807(6) _cell_measurement_reflns_used 8683 _cell_measurement_temperature 150 _cell_measurement_theta_max 72.13 _cell_measurement_theta_min 3.24 _cell_volume 4762.0(2) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2015)' _diffrn_ambient_temperature 150.0 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker D8-Venture' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.3257 _diffrn_reflns_av_unetI/netI 0.1444 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 76930 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 67.721 _diffrn_reflns_theta_min 3.240 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 5.167 _exptl_absorpt_correction_T_max 0.7536 _exptl_absorpt_correction_T_min 0.3233 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1844 before and 0.1276 after correction. The Ratio of minimum to maximum transmission is 0.4290. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.533 _exptl_crystal_description plate _exptl_crystal_F_000 2272 _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.02 _refine_diff_density_max 0.639 _refine_diff_density_min -1.147 _refine_diff_density_rms 0.167 _refine_ls_abs_structure_details ; Flack x determined using 1965 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.45(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 599 _refine_ls_number_reflns 8617 _refine_ls_number_restraints 121 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.1461 _refine_ls_R_factor_gt 0.0954 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1175P)^2^+54.3529P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2203 _refine_ls_wR_factor_ref 0.2659 _reflns_Friedel_coverage 0.952 _reflns_Friedel_fraction_full 0.996 _reflns_Friedel_fraction_max 0.996 _reflns_number_gt 6010 _reflns_number_total 8617 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0dt02529a2.cif _cod_data_source_block cu_5685g _cod_depositor_comments 'Adding full bibliography for 7705332--7705333.cif.' _cod_database_code 7705332 _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_max 0.904 _shelx_estimated_absorpt_t_min 0.492 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints Uanis(C15') \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C6') \\sim Ueq, Uanis(C5') \\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(C7') \\sim Ueq, Uanis(C2') \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C17') \\sim Ueq, Uanis(C21') \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C9') \\sim Ueq, Uanis(N2') \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004 Uanis(C10') \\sim Ueq, Uanis(C11) \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004 Uanis(C13') \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C5) \\sim Ueq, Uanis(C22') \\sim Ueq: with sigma of 0.002 and sigma for terminal atoms of 0.004 3.a Ternary CH refined with riding coordinates: C13(H13), C14(H14), C13'(H13'), C14'(H14') 3.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B), C5(H5A,H5B), C10(H10A,H10B), C11(H11A,H11B), C4'(H4'A,H4'B), C5'(H5'A,H5'B), C10'(H10C,H10D), C11'(H11C,H11D) 3.c Aromatic/amide H refined with riding coordinates: C18(H18), C19(H19), C20(H20), C21(H21), C22(H22), C18'(H18'), C19'(H19'), C20'(H20'), C21'(H21'), C22'(H22') 3.d Idealised Me refined as rotating group: C6(H6A,H6B,H6C), C12(H12A,H12B,H12C), C6'(H6'A,H6'B,H6'C), C12'(H12D,H12E,H12F) ; _shelx_res_file ; cu_5685g.res created by SHELXL-2014/7 TITL cu_5685g_a.res in Pna2(1) REM Old TITL cu_5685g in P212121 #19 REM SHELXT solution in Pna2(1) REM R1 0.136, Rweak 0.031, Alpha 0.016, Orientation a'=b, b'=a, c'=-c REM Flack x = 0.482 ( 0.042 ) from Parsons' quotients REM Formula found by SHELXT: C46 N4 O4 P S11 CELL 1.54178 15.3334 11.384 27.2807 90 90 90 ZERR 8 0.0004 0.0003 0.0006 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SYMM 0.5-X,0.5+Y,0.5+Z SFAC C H N O P S UNIT 176 168 24 16 16 32 ISOR 0.002 0.004 C15' C10 C6' C5' C12 C7' C2' C1 C17' C21' C13 C9' N2' ISOR 0.002 0.004 C10' C11 ISOR 0.002 0.004 C13' C18 C21 C5 C22' L.S. 4 PLAN 20 SIZE 0.02 0.07 0.16 TEMP -123.15 BOND $H list 4 fmap 2 ACTA OMIT -2 135.5 REM REM REM WGHT 0.117500 54.352898 FVAR 0.15541 S1 6 0.753658 0.008274 0.565004 11.00000 0.01871 0.02097 = 0.02080 -0.00081 0.00386 0.00231 S2 6 0.744628 -0.101297 0.465433 11.00000 0.02042 0.02866 = 0.03241 -0.01130 0.00640 0.00006 S3 6 0.498635 0.422193 0.574914 11.00000 0.01353 0.02703 = 0.01649 0.00075 0.00059 0.00542 S4 6 0.394914 0.423215 0.668510 11.00000 0.01298 0.03498 = 0.02201 -0.00143 0.00555 0.00429 P1 5 0.722999 0.233503 0.630553 11.00000 0.01421 0.02244 = 0.01082 0.00168 0.00119 0.00268 P2 5 0.678245 0.359535 0.523747 11.00000 0.01328 0.02209 = 0.01202 0.00194 0.00221 0.00318 O1 4 0.711794 0.618990 0.553608 11.00000 0.04389 0.02687 = 0.01370 0.00681 -0.00522 0.00406 O2 4 0.822672 0.443000 0.689856 11.00000 0.03376 0.03259 = 0.01428 -0.00425 -0.00847 0.00431 N1 3 0.715997 0.127823 0.490245 11.00000 0.01946 0.03141 = 0.01271 -0.00255 0.00369 0.00498 N2 3 0.555056 0.327958 0.652754 11.00000 0.01738 0.01894 = 0.00762 -0.00220 -0.00296 0.00143 N3 3 0.752351 0.547609 0.629875 11.00000 0.00957 0.02619 = 0.02206 -0.00179 -0.00001 0.00002 C1 1 0.729272 0.153410 0.572896 11.00000 0.01762 0.01906 = 0.01911 0.00016 0.00134 -0.00018 C2 1 0.710948 0.205169 0.529022 11.00000 0.00834 0.01971 = 0.01569 0.00298 0.00176 -0.00460 C3 1 0.736674 0.014419 0.501868 11.00000 0.01038 0.02137 = 0.01436 -0.00696 -0.00123 0.00391 C4 1 0.697404 0.164543 0.439133 11.00000 0.01569 0.02409 = 0.01580 -0.00096 0.00083 0.00174 AFIX 23 H4A 2 0.648196 0.220843 0.439086 11.00000 -1.20000 H4B 2 0.679722 0.095030 0.419724 11.00000 -1.20000 AFIX 0 C5 1 0.776280 0.221478 0.415284 11.00000 0.02125 0.02374 = 0.02177 0.00049 0.00128 0.00010 AFIX 23 H5A 2 0.794290 0.290574 0.434857 11.00000 -1.20000 H5B 2 0.825330 0.164931 0.415057 11.00000 -1.20000 AFIX 0 C6 1 0.757231 0.259539 0.363793 11.00000 0.03365 0.04985 = 0.01286 0.00517 0.00417 -0.00703 AFIX 137 H6A 2 0.743406 0.190560 0.343754 11.00000 -1.50000 H6B 2 0.808410 0.299460 0.350174 11.00000 -1.50000 H6C 2 0.707423 0.313482 0.363781 11.00000 -1.50000 AFIX 0 C7 1 0.620632 0.311663 0.617501 11.00000 0.01275 0.01232 = 0.02196 0.00152 0.00251 0.00315 C8 1 0.599705 0.356092 0.573703 11.00000 0.01194 0.01134 = 0.00966 0.00142 0.00295 -0.00080 C9 1 0.483243 0.388959 0.636585 11.00000 0.00953 0.02456 = 0.01129 -0.00608 0.00487 -0.00302 C10 1 0.561398 0.289757 0.705255 11.00000 0.02164 0.02416 = 0.02010 0.00009 0.00047 0.00049 AFIX 23 H10A 2 0.538195 0.352928 0.726514 11.00000 -1.20000 H10B 2 0.623560 0.278137 0.713781 11.00000 -1.20000 AFIX 0 C11 1 0.512347 0.178195 0.715475 11.00000 0.02514 0.02607 = 0.02414 0.00193 0.00174 0.00054 AFIX 23 H11A 2 0.517095 0.160133 0.750873 11.00000 -1.20000 H11B 2 0.449897 0.191193 0.708030 11.00000 -1.20000 AFIX 0 C12 1 0.543462 0.074029 0.686907 11.00000 0.04555 0.04311 = 0.04540 0.00320 0.00311 -0.00165 AFIX 137 H12A 2 0.532146 0.086726 0.651951 11.00000 -1.50000 H12B 2 0.512392 0.003595 0.697935 11.00000 -1.50000 H12C 2 0.606217 0.063579 0.692133 11.00000 -1.50000 AFIX 0 C13 1 0.796483 0.356875 0.609311 11.00000 0.01597 0.01822 = 0.01529 0.00105 0.00025 -0.00091 AFIX 13 H13 2 0.857428 0.326773 0.605777 11.00000 -1.20000 AFIX 0 C14 1 0.769599 0.419859 0.562200 11.00000 0.00986 0.02083 = 0.01438 -0.00444 0.00280 -0.00361 AFIX 13 H14 2 0.822358 0.428492 0.540955 11.00000 -1.20000 AFIX 0 C15 1 0.741210 0.541727 0.578942 11.00000 0.01287 0.03050 = 0.01667 0.00224 0.00247 -0.00821 C16 1 0.794339 0.451074 0.648170 11.00000 0.01307 0.02273 = 0.02023 -0.00620 -0.00606 0.00454 C17 1 0.724607 0.641511 0.661145 11.00000 0.01373 0.02372 = 0.01905 0.00582 0.00172 -0.00431 C18 1 0.742778 0.758377 0.647624 11.00000 0.01854 0.01945 = 0.01847 0.00128 0.00112 0.00135 AFIX 43 H18 2 0.772910 0.776555 0.618157 11.00000 -1.20000 AFIX 0 C19 1 0.714503 0.845986 0.679473 11.00000 0.02115 0.03377 = 0.01286 0.00350 -0.00226 -0.00465 AFIX 43 H19 2 0.726600 0.925556 0.671479 11.00000 -1.20000 AFIX 0 C20 1 0.669452 0.821998 0.722349 11.00000 0.01423 0.02590 = 0.02824 -0.00951 0.00253 0.00569 AFIX 43 H20 2 0.650460 0.883833 0.743155 11.00000 -1.20000 AFIX 0 C21 1 0.652426 0.703762 0.734410 11.00000 0.02684 0.02756 = 0.02564 -0.00030 0.00012 0.00079 AFIX 43 H21 2 0.623187 0.684664 0.764059 11.00000 -1.20000 AFIX 0 C22 1 0.678520 0.616378 0.702878 11.00000 0.02226 0.02736 = 0.01693 0.00773 -0.00799 -0.00558 AFIX 43 H22 2 0.664327 0.537044 0.710161 11.00000 -1.20000 AFIX 0 S1' 6 0.489635 0.986672 0.434846 11.00000 0.01741 0.02452 = 0.01977 0.00167 0.00227 0.00547 S2' 6 0.497667 1.092227 0.535543 11.00000 0.02000 0.02810 = 0.02855 -0.00964 0.00449 -0.00027 S3' 6 0.740923 0.566828 0.425488 11.00000 0.01160 0.02579 = 0.01662 0.00151 0.00116 0.00319 S4' 6 0.848009 0.565863 0.333109 11.00000 0.01390 0.03347 = 0.02093 -0.00164 0.00442 0.00529 P1' 5 0.521484 0.764708 0.367484 11.00000 0.01150 0.02764 = 0.01247 0.00348 0.00106 0.00417 P2' 5 0.559951 0.631709 0.474678 11.00000 0.01158 0.02132 = 0.00973 0.00169 0.00060 0.00266 O1' 4 0.522832 0.375351 0.442582 11.00000 0.03046 0.03004 = 0.01737 0.00361 -0.00933 -0.00295 O2' 4 0.432651 0.561880 0.303696 11.00000 0.03291 0.03822 = 0.01298 0.00644 -0.00937 0.00532 N1' 3 0.526204 0.863030 0.509887 11.00000 0.00738 0.03298 = 0.00967 0.00164 0.00307 0.00429 N2' 3 0.689137 0.664014 0.346189 11.00000 0.01372 0.01458 = 0.01290 0.00015 0.00134 0.00084 N3' 3 0.490036 0.448167 0.365697 11.00000 0.01563 0.02109 = 0.01530 -0.00079 0.00507 0.00570 C1' 1 0.513342 0.838623 0.426613 11.00000 0.01380 0.02238 = 0.01812 0.00036 0.00780 -0.00007 C2' 1 0.530628 0.785070 0.470199 11.00000 0.01294 0.01406 = 0.01151 -0.00136 -0.00031 -0.00082 C3' 1 0.506262 0.977378 0.497950 11.00000 0.02168 0.01165 = 0.01868 0.00006 0.01045 0.00057 C4' 1 0.542269 0.826345 0.560721 11.00000 0.00766 0.03290 = 0.01602 -0.00431 -0.00071 0.00049 AFIX 23 H4'A 2 0.560078 0.895318 0.580427 11.00000 -1.20000 H4'B 2 0.590496 0.768552 0.561461 11.00000 -1.20000 AFIX 0 C5' 1 0.460868 0.771772 0.582992 11.00000 0.02026 0.02158 = 0.02026 0.00048 0.00162 -0.00015 AFIX 23 H5'A 2 0.442084 0.703498 0.563149 11.00000 -1.20000 H5'B 2 0.412873 0.829935 0.583370 11.00000 -1.20000 AFIX 0 C6' 1 0.481872 0.732015 0.635867 11.00000 0.03735 0.04066 = 0.03491 0.00194 0.00016 -0.00200 AFIX 137 H6'A 2 0.488928 0.801201 0.656872 11.00000 -1.50000 H6'B 2 0.535992 0.686222 0.635911 11.00000 -1.50000 H6'C 2 0.434015 0.683415 0.648341 11.00000 -1.50000 AFIX 0 C7' 1 0.622843 0.683881 0.381761 11.00000 0.01602 0.01692 = 0.01638 -0.00183 0.00049 -0.00055 C8' 1 0.639394 0.633908 0.425463 11.00000 0.01266 0.01445 = 0.00768 0.00221 0.00619 0.00412 C9' 1 0.758763 0.601264 0.364834 11.00000 0.01751 0.02077 = 0.01868 -0.00085 0.00012 -0.00006 C10' 1 0.685764 0.704164 0.295205 11.00000 0.01721 0.01927 = 0.01583 -0.00031 0.00057 0.00133 AFIX 23 H10C 2 0.624402 0.720324 0.286153 11.00000 -1.20000 H10D 2 0.707564 0.640908 0.273525 11.00000 -1.20000 AFIX 0 C11' 1 0.739763 0.814216 0.287033 11.00000 0.01726 0.04513 = 0.02643 0.01473 0.00747 0.00561 AFIX 23 H11C 2 0.738229 0.834636 0.251768 11.00000 -1.20000 H11D 2 0.801137 0.797440 0.295861 11.00000 -1.20000 AFIX 0 C12' 1 0.708379 0.919198 0.316599 11.00000 0.03293 0.02808 = 0.05612 0.01169 0.02569 0.00629 AFIX 137 H12D 2 0.647436 0.935985 0.308349 11.00000 -1.50000 H12E 2 0.744455 0.987790 0.308852 11.00000 -1.50000 H12F 2 0.713011 0.901503 0.351658 11.00000 -1.50000 AFIX 0 C13' 1 0.446175 0.642722 0.386235 11.00000 0.02040 0.02114 = 0.01997 0.00203 0.00074 0.00005 AFIX 13 H13' 2 0.385041 0.672831 0.388501 11.00000 -1.20000 AFIX 0 C14' 1 0.469826 0.574844 0.433441 11.00000 0.00762 0.02747 = 0.01239 0.00645 0.00213 0.00080 AFIX 13 H14' 2 0.415708 0.566411 0.453592 11.00000 -1.20000 AFIX 0 C15' 1 0.497477 0.453213 0.416463 11.00000 0.01310 0.01442 = 0.01262 0.00048 -0.00053 -0.00065 C16' 1 0.452383 0.550389 0.346043 11.00000 0.02197 0.02497 = 0.01757 0.00838 -0.00079 0.00479 C17' 1 0.519723 0.351995 0.336001 11.00000 0.01931 0.01937 = 0.01781 -0.00019 -0.00086 -0.00009 C18' 1 0.499600 0.235089 0.346525 11.00000 0.02061 0.03156 = 0.02547 0.00787 0.00654 -0.00363 AFIX 43 H18' 2 0.466004 0.217030 0.374797 11.00000 -1.20000 AFIX 0 C19' 1 0.527526 0.146389 0.316757 11.00000 0.01533 0.02679 = 0.03418 0.00192 0.00427 -0.00733 AFIX 43 H19' 2 0.513583 0.067374 0.324761 11.00000 -1.20000 AFIX 0 C20' 1 0.576123 0.170101 0.274860 11.00000 0.03806 0.03491 = 0.01276 -0.00294 -0.00982 -0.00554 AFIX 43 H20' 2 0.595012 0.108495 0.253906 11.00000 -1.20000 AFIX 0 C21' 1 0.596266 0.286659 0.264530 11.00000 0.02330 0.02525 = 0.02202 -0.00075 0.00084 -0.00032 AFIX 43 H21' 2 0.630560 0.304139 0.236461 11.00000 -1.20000 AFIX 0 C22' 1 0.568111 0.376705 0.293623 11.00000 0.02469 0.02398 = 0.02271 0.00036 0.00018 -0.00032 AFIX 43 H22' 2 0.581261 0.455701 0.285176 11.00000 -1.20000 AFIX 0 HKLF 4 REM cu_5685g_a.res in Pna2(1) REM R1 = 0.0954 for 6010 Fo > 4sig(Fo) and 0.1461 for all 8617 data REM 599 parameters refined using 121 restraints END WGHT 0.1175 54.3989 REM Highest difference peak 0.639, deepest hole -1.147, 1-sigma level 0.167 Q1 1 0.8623 0.2561 0.6663 11.00000 0.05 0.64 Q2 1 0.3858 0.7442 0.3382 11.00000 0.05 0.63 Q3 1 0.4098 0.4348 0.6112 11.00000 0.05 0.59 Q4 1 0.6047 0.7648 0.3370 11.00000 0.05 0.59 Q5 1 0.4169 0.7165 0.5605 11.00000 0.05 0.58 Q6 1 0.8273 0.5598 0.3902 11.00000 0.05 0.56 Q7 1 0.4825 0.2903 0.5726 11.00000 0.05 0.55 Q8 1 0.6025 0.6829 0.3320 11.00000 0.05 0.55 Q9 1 0.5728 0.3439 0.5187 11.00000 0.05 0.54 Q10 1 0.6042 0.7587 0.4118 11.00000 0.05 0.54 Q11 1 0.7699 0.6423 0.3007 11.00000 0.05 0.54 Q12 1 0.6545 0.5499 0.3913 11.00000 0.05 0.53 Q13 1 0.6361 0.2397 0.5939 11.00000 0.05 0.53 Q14 1 0.5036 0.5579 0.5782 11.00000 0.05 0.53 Q15 1 0.8033 0.3253 0.6601 11.00000 0.05 0.52 Q16 1 0.8348 0.0068 0.6023 11.00000 0.05 0.52 Q17 1 0.8879 0.5750 0.3935 11.00000 0.05 0.51 Q18 1 0.4161 1.0040 0.3939 11.00000 0.05 0.51 Q19 1 0.6457 0.3210 0.6685 11.00000 0.05 0.51 Q20 1 0.4143 1.0796 0.5097 11.00000 0.05 0.51 ; _shelx_res_checksum 78974 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.7537(3) 0.0083(4) 0.56500(17) 0.0202(10) Uani 1 1 d . . . . . S2 S 0.7446(3) -0.1013(5) 0.46543(19) 0.0272(11) Uani 1 1 d . . . . . S3 S 0.4986(3) 0.4222(4) 0.57491(16) 0.0190(9) Uani 1 1 d . . . . . S4 S 0.3949(3) 0.4232(5) 0.66851(17) 0.0233(10) Uani 1 1 d . . . . . P1 P 0.7230(3) 0.2335(4) 0.63055(19) 0.0158(11) Uani 1 1 d . . . . . P2 P 0.6782(3) 0.3595(4) 0.52375(16) 0.0158(9) Uani 1 1 d . . . . . O1 O 0.7118(10) 0.6190(13) 0.5536(4) 0.028(3) Uani 1 1 d . . . . . O2 O 0.8227(9) 0.4430(13) 0.6899(5) 0.027(3) Uani 1 1 d . . . . . N1 N 0.7160(10) 0.1278(15) 0.4902(6) 0.021(4) Uani 1 1 d . . . . . N2 N 0.5551(10) 0.3280(14) 0.6528(5) 0.015(3) Uani 1 1 d . . . . . N3 N 0.7524(9) 0.5476(14) 0.6299(6) 0.019(3) Uani 1 1 d . . . . . C1 C 0.7293(12) 0.1534(16) 0.5729(7) 0.019(4) Uani 1 1 d . U . . . C2 C 0.7109(10) 0.2052(17) 0.5290(7) 0.015(4) Uani 1 1 d . . . . . C3 C 0.7367(11) 0.0144(16) 0.5019(6) 0.015(4) Uani 1 1 d . . . . . C4 C 0.6974(12) 0.1645(17) 0.4391(6) 0.019(4) Uani 1 1 d . . . . . H4A H 0.6482 0.2208 0.4391 0.022 Uiso 1 1 calc R . . . . H4B H 0.6797 0.0950 0.4197 0.022 Uiso 1 1 calc R . . . . C5 C 0.7763(13) 0.2215(19) 0.4153(7) 0.022(4) Uani 1 1 d . U . . . H5A H 0.7943 0.2906 0.4349 0.027 Uiso 1 1 calc R . . . . H5B H 0.8253 0.1649 0.4151 0.027 Uiso 1 1 calc R . . . . C6 C 0.7572(16) 0.260(2) 0.3638(8) 0.032(6) Uani 1 1 d . . . . . H6A H 0.7434 0.1906 0.3438 0.048 Uiso 1 1 calc GR . . . . H6B H 0.8084 0.2995 0.3502 0.048 Uiso 1 1 calc GR . . . . H6C H 0.7074 0.3135 0.3638 0.048 Uiso 1 1 calc GR . . . . C7 C 0.6206(11) 0.3117(16) 0.6175(7) 0.016(4) Uani 1 1 d . . . . . C8 C 0.5997(10) 0.3561(14) 0.5737(6) 0.011(3) Uani 1 1 d . . . . . C9 C 0.4832(11) 0.3890(16) 0.6366(6) 0.015(4) Uani 1 1 d . . . . . C10 C 0.5614(13) 0.2898(18) 0.7053(7) 0.022(4) Uani 1 1 d . U . . . H10A H 0.5382 0.3529 0.7265 0.026 Uiso 1 1 calc R . . . . H10B H 0.6236 0.2781 0.7138 0.026 Uiso 1 1 calc R . . . . C11 C 0.5123(14) 0.1782(18) 0.7155(8) 0.025(4) Uani 1 1 d . U . . . H11A H 0.5171 0.1601 0.7509 0.030 Uiso 1 1 calc R . . . . H11B H 0.4499 0.1912 0.7080 0.030 Uiso 1 1 calc R . . . . C12 C 0.5435(17) 0.074(2) 0.6869(10) 0.045(6) Uani 1 1 d . U . . . H12A H 0.5321 0.0867 0.6520 0.067 Uiso 1 1 calc GR . . . . H12B H 0.5124 0.0036 0.6979 0.067 Uiso 1 1 calc GR . . . . H12C H 0.6062 0.0636 0.6921 0.067 Uiso 1 1 calc GR . . . . C13 C 0.7965(12) 0.3569(16) 0.6093(6) 0.016(4) Uani 1 1 d . U . . . H13 H 0.8574 0.3268 0.6058 0.020 Uiso 1 1 calc R . . . . C14 C 0.7696(11) 0.4199(16) 0.5622(6) 0.015(4) Uani 1 1 d . . . . . H14 H 0.8224 0.4285 0.5410 0.018 Uiso 1 1 calc R . . . . C15 C 0.7412(11) 0.5417(18) 0.5789(7) 0.020(4) Uani 1 1 d . . . . . C16 C 0.7943(12) 0.4511(17) 0.6482(6) 0.019(4) Uani 1 1 d . . . . . C17 C 0.7246(12) 0.6415(17) 0.6611(7) 0.019(4) Uani 1 1 d . . . . . C18 C 0.7428(14) 0.7584(16) 0.6476(9) 0.019(5) Uani 1 1 d . U . . . H18 H 0.7729 0.7766 0.6182 0.023 Uiso 1 1 calc R . . . . C19 C 0.7145(12) 0.8460(19) 0.6795(7) 0.023(4) Uani 1 1 d . . . . . H19 H 0.7266 0.9256 0.6715 0.027 Uiso 1 1 calc R . . . . C20 C 0.6695(12) 0.8220(19) 0.7223(8) 0.023(4) Uani 1 1 d . . . . . H20 H 0.6505 0.8838 0.7432 0.027 Uiso 1 1 calc R . . . . C21 C 0.6524(14) 0.704(2) 0.7344(8) 0.027(5) Uani 1 1 d . U . . . H21 H 0.6232 0.6847 0.7641 0.032 Uiso 1 1 calc R . . . . C22 C 0.6785(12) 0.6164(18) 0.7029(7) 0.022(4) Uani 1 1 d . . . . . H22 H 0.6643 0.5370 0.7102 0.027 Uiso 1 1 calc R . . . . S1' S 0.4896(3) 0.9867(4) 0.43485(17) 0.0206(10) Uani 1 1 d . . . . . S2' S 0.4977(3) 1.0922(5) 0.53554(18) 0.0256(11) Uani 1 1 d . . . . . S3' S 0.7409(3) 0.5668(4) 0.42549(16) 0.0180(9) Uani 1 1 d . . . . . S4' S 0.8480(3) 0.5659(4) 0.33311(16) 0.0228(10) Uani 1 1 d . . . . . P1' P 0.5215(3) 0.7647(5) 0.36748(19) 0.0172(11) Uani 1 1 d . . . . . P2' P 0.5600(3) 0.6317(4) 0.47468(16) 0.0142(9) Uani 1 1 d . . . . . O1' O 0.5228(9) 0.3754(13) 0.4426(5) 0.026(3) Uani 1 1 d . . . . . O2' O 0.4327(9) 0.5619(13) 0.3037(5) 0.028(3) Uani 1 1 d . . . . . N1' N 0.5262(9) 0.8630(15) 0.5099(5) 0.017(3) Uani 1 1 d . . . . . N2' N 0.6891(9) 0.6640(13) 0.3462(5) 0.014(3) Uani 1 1 d . U . . . N3' N 0.4900(9) 0.4482(14) 0.3657(5) 0.017(3) Uani 1 1 d . . . . . C1' C 0.5133(11) 0.8386(16) 0.4266(7) 0.018(4) Uani 1 1 d . . . . . C2' C 0.5306(11) 0.7851(16) 0.4702(6) 0.013(3) Uani 1 1 d . U . . . C3' C 0.5063(12) 0.9774(16) 0.4979(6) 0.017(4) Uani 1 1 d . . . . . C4' C 0.5423(11) 0.8263(18) 0.5607(6) 0.019(4) Uani 1 1 d . . . . . H4'A H 0.5601 0.8953 0.5804 0.023 Uiso 1 1 calc R . . . . H4'B H 0.5905 0.7686 0.5615 0.023 Uiso 1 1 calc R . . . . C5' C 0.4609(13) 0.7718(18) 0.5830(7) 0.021(4) Uani 1 1 d . U . . . H5'A H 0.4421 0.7035 0.5631 0.025 Uiso 1 1 calc R . . . . H5'B H 0.4129 0.8299 0.5834 0.025 Uiso 1 1 calc R . . . . C6' C 0.4819(18) 0.732(2) 0.6359(10) 0.038(6) Uani 1 1 d . U . . . H6'A H 0.4889 0.8012 0.6569 0.056 Uiso 1 1 calc GR . . . . H6'B H 0.5360 0.6862 0.6359 0.056 Uiso 1 1 calc GR . . . . H6'C H 0.4340 0.6834 0.6483 0.056 Uiso 1 1 calc GR . . . . C7' C 0.6228(11) 0.6839(16) 0.3818(6) 0.016(4) Uani 1 1 d . U . . . C8' C 0.6394(11) 0.6339(14) 0.4255(6) 0.012(3) Uani 1 1 d . . . . . C9' C 0.7588(12) 0.6013(16) 0.3648(7) 0.019(4) Uani 1 1 d . U . . . C10' C 0.6858(12) 0.7042(16) 0.2952(6) 0.017(4) Uani 1 1 d . U . . . H10C H 0.6244 0.7203 0.2862 0.021 Uiso 1 1 calc R . . . . H10D H 0.7076 0.6409 0.2735 0.021 Uiso 1 1 calc R . . . . C11' C 0.7398(13) 0.814(2) 0.2870(8) 0.030(5) Uani 1 1 d . . . . . H11C H 0.7382 0.8346 0.2518 0.036 Uiso 1 1 calc R . . . . H11D H 0.8011 0.7974 0.2959 0.036 Uiso 1 1 calc R . . . . C12' C 0.7084(15) 0.919(2) 0.3166(9) 0.039(6) Uani 1 1 d . . . . . H12D H 0.6474 0.9360 0.3083 0.059 Uiso 1 1 calc GR . . . . H12E H 0.7445 0.9878 0.3089 0.059 Uiso 1 1 calc GR . . . . H12F H 0.7130 0.9015 0.3517 0.059 Uiso 1 1 calc GR . . . . C13' C 0.4462(12) 0.6427(17) 0.3862(7) 0.021(4) Uani 1 1 d . U . . . H13' H 0.3850 0.6728 0.3885 0.025 Uiso 1 1 calc R . . . . C14' C 0.4698(11) 0.5748(17) 0.4334(6) 0.016(4) Uani 1 1 d . . . . . H14' H 0.4157 0.5664 0.4536 0.019 Uiso 1 1 calc R . . . . C15' C 0.4975(11) 0.4532(16) 0.4165(6) 0.013(4) Uani 1 1 d . U . . . C16' C 0.4524(12) 0.5504(18) 0.3460(7) 0.022(4) Uani 1 1 d . . . . . C17' C 0.5197(12) 0.3520(17) 0.3360(7) 0.019(4) Uani 1 1 d . U . . . C18' C 0.4996(14) 0.2351(19) 0.3465(9) 0.026(5) Uani 1 1 d . . . . . H18' H 0.4660 0.2170 0.3748 0.031 Uiso 1 1 calc R . . . . C19' C 0.5275(13) 0.1464(19) 0.3168(8) 0.025(5) Uani 1 1 d . . . . . H19' H 0.5136 0.0674 0.3248 0.031 Uiso 1 1 calc R . . . . C20' C 0.5761(15) 0.170(2) 0.2749(7) 0.029(5) Uani 1 1 d . . . . . H20' H 0.5950 0.1085 0.2539 0.034 Uiso 1 1 calc R . . . . C21' C 0.5963(14) 0.2867(19) 0.2645(7) 0.024(4) Uani 1 1 d . U . . . H21' H 0.6306 0.3041 0.2365 0.028 Uiso 1 1 calc R . . . . C22' C 0.5681(13) 0.3767(19) 0.2936(7) 0.024(4) Uani 1 1 d . U . . . H22' H 0.5813 0.4557 0.2852 0.029 Uiso 1 1 calc R . . . . 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 0.019(2) 0.021(2) 0.021(2) -0.0008(19) 0.0039(18) 0.0023(19) S2 0.020(2) 0.029(3) 0.032(3) -0.011(2) 0.006(2) 0.000(2) S3 0.014(2) 0.027(2) 0.016(2) 0.0008(18) 0.0006(16) 0.0054(19) S4 0.013(2) 0.035(3) 0.022(2) -0.001(2) 0.0056(18) 0.004(2) P1 0.014(2) 0.022(2) 0.011(2) 0.0017(19) 0.001(2) 0.0027(19) P2 0.013(2) 0.022(2) 0.012(2) 0.0019(18) 0.0022(17) 0.0032(18) O1 0.044(9) 0.027(8) 0.014(7) 0.007(6) -0.005(6) 0.004(7) O2 0.034(8) 0.033(8) 0.014(6) -0.004(6) -0.008(6) 0.004(6) N1 0.019(8) 0.031(9) 0.013(8) -0.003(7) 0.004(6) 0.005(7) N2 0.017(7) 0.019(7) 0.008(7) -0.002(5) -0.003(5) 0.001(6) N3 0.010(7) 0.026(9) 0.022(8) -0.002(7) 0.000(6) 0.000(6) C1 0.018(4) 0.019(4) 0.019(4) 0.000(3) 0.001(3) 0.000(3) C2 0.008(8) 0.020(9) 0.016(8) 0.003(7) 0.002(6) -0.005(7) C3 0.010(8) 0.021(10) 0.014(9) -0.007(7) -0.001(7) 0.004(7) C4 0.016(9) 0.024(10) 0.016(9) -0.001(7) 0.001(7) 0.002(8) C5 0.021(5) 0.024(5) 0.022(5) 0.000(3) 0.001(3) 0.000(3) C6 0.034(12) 0.050(14) 0.013(10) 0.005(9) 0.004(9) -0.007(10) C7 0.013(8) 0.012(8) 0.022(9) 0.002(7) 0.003(6) 0.003(7) C8 0.012(8) 0.011(8) 0.010(8) 0.001(6) 0.003(7) -0.001(7) C9 0.010(8) 0.025(9) 0.011(8) -0.006(7) 0.005(6) -0.003(7) C10 0.022(5) 0.024(5) 0.020(5) 0.000(3) 0.000(3) 0.000(3) C11 0.025(5) 0.026(5) 0.024(5) 0.002(3) 0.002(3) 0.001(3) C12 0.046(7) 0.043(8) 0.045(7) 0.003(5) 0.003(5) -0.002(5) C13 0.016(4) 0.018(4) 0.015(4) 0.001(3) 0.000(3) -0.001(3) C14 0.010(8) 0.021(9) 0.014(8) -0.004(8) 0.003(7) -0.004(7) C15 0.013(8) 0.030(10) 0.017(9) 0.002(8) 0.002(7) -0.008(8) C16 0.013(9) 0.023(9) 0.020(9) -0.006(8) -0.006(7) 0.005(8) C17 0.014(9) 0.024(9) 0.019(9) 0.006(8) 0.002(7) -0.004(7) C18 0.019(5) 0.019(5) 0.018(5) 0.001(3) 0.001(3) 0.001(3) C19 0.021(10) 0.034(11) 0.013(9) 0.003(8) -0.002(8) -0.005(9) C20 0.014(9) 0.026(11) 0.028(11) -0.010(9) 0.003(8) 0.006(8) C21 0.027(5) 0.028(5) 0.026(5) 0.000(3) 0.000(3) 0.001(3) C22 0.022(9) 0.027(10) 0.017(9) 0.008(8) -0.008(7) -0.006(8) S1' 0.017(2) 0.025(2) 0.020(2) 0.002(2) 0.0023(18) 0.005(2) S2' 0.020(2) 0.028(3) 0.029(3) -0.010(2) 0.0045(19) 0.000(2) S3' 0.012(2) 0.026(2) 0.017(2) 0.0015(19) 0.0012(16) 0.0032(18) S4' 0.014(2) 0.033(3) 0.021(2) -0.002(2) 0.0044(18) 0.005(2) P1' 0.011(2) 0.028(3) 0.012(3) 0.0035(19) 0.001(2) 0.004(2) P2' 0.012(2) 0.021(2) 0.010(2) 0.0017(18) 0.0006(16) 0.0027(18) O1' 0.030(8) 0.030(8) 0.017(7) 0.004(6) -0.009(6) -0.003(6) O2' 0.033(8) 0.038(8) 0.013(6) 0.006(6) -0.009(6) 0.005(7) N1' 0.007(7) 0.033(9) 0.010(7) 0.002(6) 0.003(5) 0.004(6) N2' 0.014(4) 0.015(4) 0.013(4) 0.000(3) 0.001(3) 0.001(3) N3' 0.016(8) 0.021(8) 0.015(7) -0.001(6) 0.005(6) 0.006(6) C1' 0.014(8) 0.022(9) 0.018(9) 0.000(7) 0.008(7) 0.000(7) C2' 0.013(4) 0.014(4) 0.012(4) -0.001(3) 0.000(3) -0.001(3) C3' 0.022(9) 0.012(9) 0.019(9) 0.000(7) 0.010(7) 0.001(7) C4' 0.008(8) 0.033(11) 0.016(9) -0.004(8) -0.001(7) 0.000(8) C5' 0.020(5) 0.022(5) 0.020(5) 0.000(3) 0.002(3) 0.000(3) C6' 0.037(8) 0.041(7) 0.035(8) 0.002(5) 0.000(5) -0.002(5) C7' 0.016(4) 0.017(4) 0.016(4) -0.002(3) 0.000(3) -0.001(3) C8' 0.013(8) 0.014(8) 0.008(8) 0.002(7) 0.006(7) 0.004(7) C9' 0.018(5) 0.021(5) 0.019(5) -0.001(3) 0.000(3) 0.000(3) C10' 0.017(4) 0.019(4) 0.016(4) 0.000(3) 0.001(3) 0.001(3) C11' 0.017(10) 0.045(13) 0.026(10) 0.015(9) 0.007(8) 0.006(9) C12' 0.033(12) 0.028(11) 0.056(15) 0.012(10) 0.026(11) 0.006(10) C13' 0.020(5) 0.021(5) 0.020(5) 0.002(3) 0.001(3) 0.000(3) C14' 0.008(8) 0.027(10) 0.012(8) 0.006(7) 0.002(7) 0.001(7) C15' 0.013(4) 0.014(4) 0.013(4) 0.000(3) -0.001(3) -0.001(3) C16' 0.022(10) 0.025(10) 0.018(9) 0.008(8) -0.001(7) 0.005(8) C17' 0.019(5) 0.019(5) 0.018(5) 0.000(3) -0.001(3) 0.000(3) C18' 0.021(10) 0.032(11) 0.025(11) 0.008(9) 0.007(8) -0.004(9) C19' 0.015(10) 0.027(11) 0.034(12) 0.002(9) 0.004(9) -0.007(8) C20' 0.038(13) 0.035(12) 0.013(10) -0.003(9) -0.010(9) -0.006(10) C21' 0.023(5) 0.025(5) 0.022(5) -0.001(3) 0.001(3) 0.000(3) C22' 0.025(5) 0.024(5) 0.023(5) 0.000(3) 0.000(3) 0.000(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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 C1 S1 C3 93.0(9) . . ? C8 S3 C9 92.6(8) . . ? C1 P1 C7 96.9(9) . . ? C1 P1 C13 94.3(8) . . ? C7 P1 C13 95.2(8) . . ? C2 P2 C14 95.9(8) . . ? C8 P2 C2 95.8(8) . . ? C8 P2 C14 94.8(8) . . ? C2 N1 C4 122.0(16) . . ? C3 N1 C2 116.0(15) . . ? C3 N1 C4 121.9(15) . . ? C7 N2 C10 124.7(15) . . ? C9 N2 C7 114.9(14) . . ? C9 N2 C10 120.3(14) . . ? C15 N3 C17 126.2(16) . . ? C16 N3 C15 112.4(16) . . ? C16 N3 C17 121.5(15) . . ? S1 C1 P1 127.2(11) . . ? C2 C1 S1 110.6(14) . . ? C2 C1 P1 122.1(15) . . ? N1 C2 P2 124.6(13) . . ? C1 C2 P2 122.7(15) . . ? C1 C2 N1 112.7(17) . . ? S2 C3 S1 123.4(11) . . ? N1 C3 S1 107.6(12) . . ? N1 C3 S2 129.0(14) . . ? N1 C4 H4A 109.3 . . ? N1 C4 H4B 109.3 . . ? N1 C4 C5 111.7(15) . . ? H4A C4 H4B 107.9 . . ? C5 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C4 C5 H5A 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C6 C5 C4 111.7(17) . . ? C6 C5 H5A 109.3 . . ? C6 C5 H5B 109.3 . . ? C5 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C5 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 P1 122.9(13) . . ? C8 C7 P1 124.1(13) . . ? C8 C7 N2 113.0(15) . . ? S3 C8 P2 126.9(9) . . ? C7 C8 S3 111.3(12) . . ? C7 C8 P2 121.3(13) . . ? S4 C9 S3 124.6(11) . . ? N2 C9 S3 108.1(11) . . ? N2 C9 S4 127.2(13) . . ? N2 C10 H10A 109.0 . . ? N2 C10 H10B 109.0 . . ? N2 C10 C11 112.9(16) . . ? H10A C10 H10B 107.8 . . ? C11 C10 H10A 109.0 . . ? C11 C10 H10B 109.0 . . ? C10 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C12 C11 C10 114.4(19) . . ? C12 C11 H11A 108.7 . . ? C12 C11 H11B 108.7 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12B 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? P1 C13 H13 109.4 . . ? C14 C13 P1 116.4(12) . . ? C14 C13 H13 109.4 . . ? C16 C13 P1 107.4(13) . . ? C16 C13 H13 109.4 . . ? C16 C13 C14 104.6(14) . . ? P2 C14 H14 108.4 . . ? C13 C14 P2 119.9(13) . . ? C13 C14 H14 108.4 . . ? C15 C14 P2 106.7(12) . . ? C15 C14 C13 104.6(14) . . ? C15 C14 H14 108.4 . . ? O1 C15 N3 125.4(19) . . ? O1 C15 C14 126.8(17) . . ? N3 C15 C14 107.8(16) . . ? O2 C16 N3 124.6(17) . . ? O2 C16 C13 126.4(17) . . ? N3 C16 C13 109.0(15) . . ? C18 C17 N3 119.4(17) . . ? C22 C17 N3 119.5(18) . . ? C22 C17 C18 121.1(19) . . ? C17 C18 H18 121.6 . . ? C19 C18 C17 117(2) . . ? C19 C18 H18 121.6 . . ? C18 C19 H19 118.6 . . ? C20 C19 C18 123(2) . . ? C20 C19 H19 118.6 . . ? C19 C20 H20 120.7 . . ? C19 C20 C21 118.5(18) . . ? C21 C20 H20 120.7 . . ? C20 C21 H21 120.3 . . ? C22 C21 C20 119.4(19) . . ? C22 C21 H21 120.3 . . ? C17 C22 C21 121(2) . . ? C17 C22 H22 119.4 . . ? C21 C22 H22 119.4 . . ? C1' S1' C3' 92.2(9) . . ? C9' S3' C8' 92.4(8) . . ? C1' P1' C7' 95.8(8) . . ? C1' P1' C13' 93.3(8) . . ? C7' P1' C13' 95.3(8) . . ? C2' P2' C8' 96.0(8) . . ? C2' P2' C14' 96.2(8) . . ? C8' P2' C14' 93.2(8) . . ? C2' N1' C4' 122.8(16) . . ? C3' N1' C2' 115.3(14) . . ? C3' N1' C4' 122.0(15) . . ? C7' N2' C10' 124.9(14) . . ? C9' N2' C7' 112.5(14) . . ? C9' N2' C10' 122.6(14) . . ? C15' N3' C16' 112.3(15) . . ? C15' N3' C17' 124.6(15) . . ? C16' N3' C17' 123.1(15) . . ? S1' C1' P1' 125.2(11) . . ? C2' C1' S1' 111.2(14) . . ? C2' C1' P1' 123.5(14) . . ? N1' C2' P2' 124.9(13) . . ? C1' C2' P2' 122.7(14) . . ? C1' C2' N1' 112.4(16) . . ? S2' C3' S1' 123.3(11) . . ? N1' C3' S1' 108.9(12) . . ? N1' C3' S2' 127.9(14) . . ? N1' C4' H4'A 109.5 . . ? N1' C4' H4'B 109.5 . . ? N1' C4' C5' 110.8(14) . . ? H4'A C4' H4'B 108.1 . . ? C5' C4' H4'A 109.5 . . ? C5' C4' H4'B 109.5 . . ? C4' C5' H5'A 109.9 . . ? C4' C5' H5'B 109.9 . . ? C4' C5' C6' 108.7(17) . . ? H5'A C5' H5'B 108.3 . . ? C6' C5' H5'A 109.9 . . ? C6' C5' H5'B 109.9 . . ? C5' C6' H6'A 109.5 . . ? C5' C6' H6'B 109.5 . . ? C5' C6' H6'C 109.5 . . ? H6'A C6' H6'B 109.5 . . ? H6'A C6' H6'C 109.5 . . ? H6'B C6' H6'C 109.5 . . ? N2' C7' P1' 122.4(13) . . ? C8' C7' P1' 123.8(13) . . ? C8' C7' N2' 113.7(15) . . ? S3' C8' P2' 126.6(9) . . ? C7' C8' S3' 110.9(12) . . ? C7' C8' P2' 122.4(13) . . ? S4' C9' S3' 125.0(11) . . ? N2' C9' S3' 110.4(13) . . ? N2' C9' S4' 124.6(14) . . ? N2' C10' H10C 109.2 . . ? N2' C10' H10D 109.2 . . ? N2' C10' C11' 112.2(15) . . ? H10C C10' H10D 107.9 . . ? C11' C10' H10C 109.2 . . ? C11' C10' H10D 109.2 . . ? C10' C11' H11C 108.9 . . ? C10' C11' H11D 108.9 . . ? C10' C11' C12' 113.5(17) . . ? H11C C11' H11D 107.7 . . ? C12' C11' H11C 108.9 . . ? C12' C11' H11D 108.9 . . ? C11' C12' H12D 109.5 . . ? C11' C12' H12E 109.5 . . ? C11' C12' H12F 109.5 . . ? H12D C12' H12E 109.5 . . ? H12D C12' H12F 109.5 . . ? H12E C12' H12F 109.5 . . ? P1' C13' H13' 109.9 . . ? C14' C13' P1' 116.9(13) . . ? C14' C13' H13' 109.9 . . ? C16' C13' P1' 106.0(13) . . ? C16' C13' H13' 109.9 . . ? C16' C13' C14' 103.9(15) . . ? P2' C14' H14' 108.1 . . ? C13' C14' P2' 119.7(13) . . ? C13' C14' H14' 108.1 . . ? C15' C14' P2' 106.8(12) . . ? C15' C14' C13' 105.5(15) . . ? C15' C14' H14' 108.1 . . ? O1' C15' N3' 125.9(17) . . ? O1' C15' C14' 125.5(16) . . ? N3' C15' C14' 108.5(15) . . ? O2' C16' N3' 124.1(18) . . ? O2' C16' C13' 127.0(18) . . ? N3' C16' C13' 108.8(15) . . ? C18' C17' N3' 122.7(18) . . ? C18' C17' C22' 118.5(19) . . ? C22' C17' N3' 118.7(18) . . ? C17' C18' H18' 119.5 . . ? C19' C18' C17' 121(2) . . ? C19' C18' H18' 119.5 . . ? C18' C19' H19' 119.6 . . ? C18' C19' C20' 121(2) . . ? C20' C19' H19' 119.6 . . ? C19' C20' H20' 121.0 . . ? C19' C20' C21' 118(2) . . ? C21' C20' H20' 121.0 . . ? C20' C21' H21' 119.1 . . ? C22' C21' C20' 122(2) . . ? C22' C21' H21' 119.1 . . ? C17' C22' H22' 120.1 . . ? C21' C22' C17' 120(2) . . ? C21' C22' H22' 120.1 . . ? 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 C1 1.708(19) . ? S1 C3 1.743(17) . ? S2 C3 1.655(18) . ? S3 C8 1.723(16) . ? S3 C9 1.741(17) . ? S4 C9 1.657(16) . ? P1 C1 1.82(2) . ? P1 C7 1.839(18) . ? P1 C13 1.892(18) . ? P2 C2 1.833(19) . ? P2 C8 1.819(16) . ? P2 C14 1.880(18) . ? O1 C15 1.21(2) . ? O2 C16 1.22(2) . ? N1 C2 1.38(2) . ? N1 C3 1.37(3) . ? N1 C4 1.48(2) . ? N2 C7 1.40(2) . ? N2 C9 1.37(2) . ? N2 C10 1.50(2) . ? N3 C15 1.40(2) . ? N3 C16 1.37(2) . ? N3 C17 1.43(2) . ? C1 C2 1.36(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.52(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C5 C6 1.50(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C8 1.34(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C10 C11 1.50(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.50(3) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13 1.0000 . ? C13 C14 1.53(2) . ? C13 C16 1.51(2) . ? C14 H14 1.0000 . ? C14 C15 1.52(3) . ? C17 C18 1.41(3) . ? C17 C22 1.37(3) . ? C18 H18 0.9500 . ? C18 C19 1.39(3) . ? C19 H19 0.9500 . ? C19 C20 1.39(3) . ? C20 H20 0.9500 . ? C20 C21 1.41(3) . ? C21 H21 0.9500 . ? C21 C22 1.37(3) . ? C22 H22 0.9500 . ? S1' C1' 1.739(19) . ? S1' C3' 1.744(18) . ? S2' C3' 1.667(18) . ? S3' C8' 1.734(16) . ? S3' C9' 1.722(18) . ? S4' C9' 1.669(18) . ? P1' C1' 1.824(19) . ? P1' C7' 1.848(18) . ? P1' C13' 1.877(19) . ? P2' C2' 1.807(19) . ? P2' C8' 1.813(16) . ? P2' C14' 1.896(18) . ? O1' C15' 1.20(2) . ? O2' C16' 1.20(2) . ? N1' C2' 1.40(2) . ? N1' C3' 1.38(2) . ? N1' C4' 1.47(2) . ? N2' C7' 1.42(2) . ? N2' C9' 1.38(2) . ? N2' C10' 1.46(2) . ? N3' C15' 1.39(2) . ? N3' C16' 1.41(2) . ? N3' C17' 1.44(2) . ? C1' C2' 1.36(3) . ? C4' H4'A 0.9900 . ? C4' H4'B 0.9900 . ? C4' C5' 1.52(3) . ? C5' H5'A 0.9900 . ? C5' H5'B 0.9900 . ? C5' C6' 1.55(3) . ? C6' H6'A 0.9800 . ? C6' H6'B 0.9800 . ? C6' H6'C 0.9800 . ? C7' C8' 1.35(2) . ? C10' H10C 0.9900 . ? C10' H10D 0.9900 . ? C10' C11' 1.52(3) . ? C11' H11C 0.9900 . ? C11' H11D 0.9900 . ? C11' C12' 1.52(3) . ? C12' H12D 0.9800 . ? C12' H12E 0.9800 . ? C12' H12F 0.9800 . ? C13' H13' 1.0000 . ? C13' C14' 1.55(2) . ? C13' C16' 1.52(3) . ? C14' H14' 1.0000 . ? C14' C15' 1.52(2) . ? C17' C18' 1.40(3) . ? C17' C22' 1.40(3) . ? C18' H18' 0.9500 . ? C18' C19' 1.36(3) . ? C19' H19' 0.9500 . ? C19' C20' 1.39(3) . ? C20' H20' 0.9500 . ? C20' C21' 1.39(3) . ? C21' H21' 0.9500 . ? C21' C22' 1.37(3) . ? C22' H22' 0.9500 . ?