#------------------------------------------------------------------------------ #$Date: 2019-06-15 05:54:36 +0300 (Sat, 15 Jun 2019) $ #$Revision: 215997 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/69/7156915.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_7156915 loop_ _publ_author_name 'Gogoi, Pranjal' 'Neog, Kashmiri' 'Dutta, Dhiraj' 'Das, Babulal' _publ_section_title ; Aryne Insertion into P=O Bond: One-pot Synthesis of Quaternary Phosphonium Triflates ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB01157A _journal_year 2019 _chemical_formula_sum 'C31 H24 F3 O4 P S' _chemical_formula_weight 580.53 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-01-02 deposited with the CCDC. 2019-06-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.992(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.5734(4) _cell_length_b 15.0468(7) _cell_length_c 19.4977(9) _cell_measurement_reflns_used 3084 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 24.999 _cell_measurement_theta_min 1.710 _cell_volume 2804.8(2) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0491 _diffrn_reflns_av_unetI/netI 0.0371 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 30535 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 1.710 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.375 _exptl_crystal_description blocks _exptl_crystal_F_000 1200 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.13 _refine_diff_density_max 1.047 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.057 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.982 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 361 _refine_ls_number_reflns 4938 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.982 _refine_ls_R_factor_all 0.1100 _refine_ls_R_factor_gt 0.0725 _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^)+(0.0833P)^2^+3.8146P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1785 _refine_ls_wR_factor_ref 0.2035 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3084 _reflns_number_total 4938 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob01157a2.cif _cod_data_source_block KN-334_0m _cod_database_code 7156915 _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_res_file ; KN-334_0m.res created by SHELXL-2014/7 TITL KN-334_0m in P2(1)/n CELL 0.71073 9.5734 15.0468 19.4977 90.000 92.992 90.000 ZERR 4.00 0.0004 0.0007 0.0009 0.000 0.003 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H O P S F UNIT 124 96 16 4 4 12 OMIT -3 50 L.S. 20 ACTA BOND FMAP 2 PLAN 4 TEMP 23.000 WGHT 0.083300 3.814600 FVAR 0.41858 MOLE 1 P1 4 0.297124 0.428692 0.193002 11.00000 0.04827 0.05163 = 0.06131 -0.00444 -0.00023 0.00086 O1 3 0.496021 0.277239 0.198372 11.00000 0.06360 0.05725 = 0.07877 0.00882 0.01912 0.00892 C7 1 0.541829 0.343156 0.157075 11.00000 0.05406 0.05581 = 0.05223 -0.00383 0.00399 -0.00391 C12 1 0.456646 0.417939 0.149658 11.00000 0.05152 0.05578 = 0.05790 -0.00445 -0.00099 -0.00354 C13 1 0.205008 0.523142 0.158146 11.00000 0.05164 0.05292 = 0.06844 -0.00534 0.00086 0.00046 C25 1 0.187391 0.333968 0.178515 11.00000 0.04769 0.05344 = 0.06246 -0.00007 -0.00182 0.00074 C8 1 0.667281 0.339798 0.125041 11.00000 0.05326 0.06588 = 0.07601 -0.00499 0.00757 -0.00091 AFIX 43 H8 2 0.724903 0.290252 0.130368 11.00000 -1.20000 AFIX 0 C24 1 0.228106 0.486284 0.320571 11.00000 0.05489 0.07872 = 0.06913 -0.01559 -0.00388 0.01198 AFIX 43 H24 2 0.144440 0.504497 0.298564 11.00000 -1.20000 AFIX 0 C20 1 0.455649 0.421315 0.316568 11.00000 0.05499 0.06334 = 0.07191 -0.01048 -0.00558 0.00348 AFIX 43 H20 2 0.525804 0.395335 0.292102 11.00000 -1.20000 AFIX 0 C10 1 0.623993 0.483415 0.076311 11.00000 0.07186 0.07005 = 0.08182 0.00714 0.01306 -0.01130 AFIX 43 H10 2 0.651978 0.530157 0.049000 11.00000 -1.20000 AFIX 0 C1 1 0.562118 0.193617 0.197435 11.00000 0.04687 0.05857 = 0.07841 0.00479 0.00872 0.00234 C19 1 0.330971 0.447770 0.282956 11.00000 0.05302 0.05449 = 0.06210 -0.00860 -0.00399 -0.00223 C14 1 0.099470 0.513111 0.107734 11.00000 0.06572 0.06471 = 0.07441 -0.00452 -0.01166 0.00315 AFIX 43 H14 2 0.071975 0.456549 0.093318 11.00000 -1.20000 AFIX 0 C23 1 0.249143 0.497669 0.390147 11.00000 0.07033 0.09084 = 0.06934 -0.02498 0.00397 0.00716 AFIX 43 H23 2 0.179737 0.523620 0.415124 11.00000 -1.20000 AFIX 0 C30 1 0.086254 0.313254 0.225185 11.00000 0.05959 0.07258 = 0.06513 -0.00119 -0.00009 -0.00561 AFIX 43 H30 2 0.081219 0.345802 0.265529 11.00000 -1.20000 AFIX 0 C11 1 0.499368 0.487235 0.108129 11.00000 0.06263 0.05877 = 0.07325 0.00527 0.00507 -0.00212 AFIX 43 H11 2 0.442458 0.536970 0.101846 11.00000 -1.20000 AFIX 0 C26 1 0.193091 0.284981 0.119151 11.00000 0.05790 0.06686 = 0.07714 -0.01628 0.00903 -0.00551 AFIX 43 H26 2 0.259877 0.298163 0.087709 11.00000 -1.20000 AFIX 0 C28 1 0.002248 0.196204 0.152696 11.00000 0.06290 0.06323 = 0.10837 -0.00023 -0.01382 -0.01117 AFIX 43 H28 2 -0.058982 0.149048 0.144099 11.00000 -1.20000 AFIX 0 C21 1 0.474512 0.433892 0.386488 11.00000 0.07319 0.08053 = 0.07306 -0.01080 -0.01921 0.00601 AFIX 43 H21 2 0.558154 0.416913 0.409160 11.00000 -1.20000 AFIX 0 C18 1 0.240930 0.608094 0.179933 11.00000 0.06758 0.06016 = 0.09112 -0.00398 -0.01410 0.00255 AFIX 43 H18 2 0.309756 0.616013 0.214847 11.00000 -1.20000 AFIX 0 C16 1 0.072899 0.669629 0.099318 11.00000 0.07630 0.06900 = 0.10728 0.01339 0.00182 0.01728 AFIX 43 H16 2 0.029367 0.718874 0.078832 11.00000 -1.20000 AFIX 0 C9 1 0.706019 0.409586 0.085582 11.00000 0.06278 0.08305 = 0.07811 -0.00289 0.01981 -0.01304 AFIX 43 H9 2 0.790702 0.406842 0.064377 11.00000 -1.20000 AFIX 0 C2 1 0.552723 0.141993 0.139789 11.00000 0.07104 0.07232 = 0.08094 -0.00473 0.00549 -0.00307 AFIX 43 H2 2 0.505504 0.162724 0.100068 11.00000 -1.20000 AFIX 0 C29 1 -0.006101 0.244368 0.211221 11.00000 0.05749 0.08046 = 0.08940 0.00897 0.00332 -0.01211 AFIX 43 H29 2 -0.074147 0.230927 0.241947 11.00000 -1.20000 AFIX 0 C22 1 0.370904 0.471192 0.422668 11.00000 0.08129 0.08263 = 0.06575 -0.01561 -0.00792 -0.00095 AFIX 43 H22 2 0.383961 0.478479 0.469933 11.00000 -1.20000 AFIX 0 C17 1 0.175043 0.681033 0.150062 11.00000 0.07872 0.05629 = 0.12019 -0.00066 0.00148 0.00711 AFIX 43 H17 2 0.200224 0.737995 0.164501 11.00000 -1.20000 AFIX 0 C27 1 0.099854 0.216303 0.106182 11.00000 0.07650 0.07033 = 0.09759 -0.02747 -0.00141 -0.00648 AFIX 43 H27 2 0.103315 0.183640 0.065813 11.00000 -1.20000 AFIX 0 C15 1 0.034930 0.586916 0.078804 11.00000 0.07487 0.08488 = 0.08389 0.00583 -0.01478 0.01126 AFIX 43 H15 2 -0.035739 0.579729 0.044688 11.00000 -1.20000 AFIX 0 C4 1 0.679202 0.030203 0.199074 11.00000 0.07074 0.07401 = 0.18849 0.01581 0.02775 0.01430 AFIX 43 H4 2 0.719159 -0.026148 0.199746 11.00000 -1.20000 AFIX 0 C6 1 0.630111 0.165516 0.256396 11.00000 0.06451 0.09276 = 0.08266 0.00914 0.00051 0.00326 AFIX 43 H6 2 0.637198 0.201598 0.295148 11.00000 -1.20000 AFIX 0 C5 1 0.688900 0.080720 0.256809 11.00000 0.08169 0.10941 = 0.13029 0.04629 -0.00422 0.01955 AFIX 43 H5 2 0.734638 0.058829 0.296539 11.00000 -1.20000 AFIX 0 C3 1 0.612999 0.059839 0.140805 11.00000 0.07340 0.06869 = 0.14130 -0.01982 0.02698 -0.00101 AFIX 43 H3 2 0.608448 0.024550 0.101593 11.00000 -1.20000 AFIX 0 MOLE 2 S1 5 0.687287 0.793246 0.067695 11.00000 0.08880 0.11283 = 0.10567 0.01743 -0.00084 -0.00711 O3 3 0.727760 0.820542 0.136341 11.00000 0.18302 0.15860 = 0.10950 0.01801 -0.06036 -0.06622 O4 3 0.680047 0.864661 0.017590 11.00000 0.21545 0.12206 = 0.11797 0.06412 0.01753 -0.04316 O2 3 0.748030 0.710456 0.045662 11.00000 0.16174 0.15027 = 0.19325 0.03232 0.07884 0.07606 C31 1 0.512810 0.766252 0.071862 11.00000 0.12965 0.12671 = 0.10679 -0.01977 0.01291 -0.01166 F1 6 0.504258 0.701088 0.121518 11.00000 0.24338 0.14170 = 0.16183 0.01525 0.07777 -0.08250 F3 6 0.440375 0.834293 0.093094 11.00000 0.14134 0.17992 = 0.27695 0.01377 0.06702 0.06871 F2 6 0.457474 0.735396 0.016281 11.00000 0.22428 0.33585 = 0.14502 -0.02362 -0.06490 -0.14849 HKLF 4 REM KN-334_0m in P2(1)/n REM R1 = 0.0725 for 3084 Fo > 4sig(Fo) and 0.1100 for all 4938 data REM 361 parameters refined using 0 restraints END WGHT 0.1232 1.5148 REM Highest difference peak 1.047, deepest hole -0.452, 1-sigma level 0.057 Q1 1 0.6597 0.7429 0.1001 11.00000 0.05 1.05 Q2 1 0.5357 0.8899 0.0244 11.00000 0.05 0.53 Q3 1 0.5921 0.6978 0.0034 11.00000 0.05 0.46 Q4 1 0.6261 0.6801 0.1143 11.00000 0.05 0.36 ; _shelx_res_checksum 8491 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 P1 P 0.29712(10) 0.42869(7) 0.19300(5) 0.0538(3) Uani 1 1 d . . O1 O 0.4960(3) 0.27724(18) 0.19837(15) 0.0660(8) Uani 1 1 d . . C7 C 0.5418(4) 0.3432(3) 0.15707(19) 0.0540(9) Uani 1 1 d . . C12 C 0.4566(4) 0.4179(3) 0.1497(2) 0.0552(9) Uani 1 1 d . . C13 C 0.2050(4) 0.5231(3) 0.1581(2) 0.0577(10) Uani 1 1 d . . C25 C 0.1874(4) 0.3340(3) 0.1785(2) 0.0547(9) Uani 1 1 d . . C8 C 0.6673(4) 0.3398(3) 0.1250(2) 0.0649(11) Uani 1 1 d . . H8 H 0.7249 0.2903 0.1304 0.078 Uiso 1 1 calc R U C24 C 0.2281(4) 0.4863(3) 0.3206(2) 0.0678(12) Uani 1 1 d . . H24 H 0.1444 0.5045 0.2986 0.081 Uiso 1 1 calc R U C20 C 0.4556(4) 0.4213(3) 0.3166(2) 0.0637(11) Uani 1 1 d . . H20 H 0.5258 0.3953 0.2921 0.076 Uiso 1 1 calc R U C10 C 0.6240(5) 0.4834(3) 0.0763(2) 0.0743(12) Uani 1 1 d . . H10 H 0.6520 0.5302 0.0490 0.089 Uiso 1 1 calc R U C1 C 0.5621(4) 0.1936(3) 0.1974(2) 0.0611(10) Uani 1 1 d . . C19 C 0.3310(4) 0.4478(3) 0.2830(2) 0.0568(10) Uani 1 1 d . . C14 C 0.0995(4) 0.5131(3) 0.1077(2) 0.0688(11) Uani 1 1 d . . H14 H 0.0720 0.4565 0.0933 0.083 Uiso 1 1 calc R U C23 C 0.2491(5) 0.4977(3) 0.3901(2) 0.0768(13) Uani 1 1 d . . H23 H 0.1797 0.5236 0.4151 0.092 Uiso 1 1 calc R U C30 C 0.0863(4) 0.3133(3) 0.2252(2) 0.0659(11) Uani 1 1 d . . H30 H 0.0812 0.3458 0.2655 0.079 Uiso 1 1 calc R U C11 C 0.4994(4) 0.4872(3) 0.1081(2) 0.0648(11) Uani 1 1 d . . H11 H 0.4425 0.5370 0.1018 0.078 Uiso 1 1 calc R U C26 C 0.1931(4) 0.2850(3) 0.1192(2) 0.0671(11) Uani 1 1 d . . H26 H 0.2599 0.2982 0.0877 0.081 Uiso 1 1 calc R U C28 C 0.0022(5) 0.1962(3) 0.1527(3) 0.0788(13) Uani 1 1 d . . H28 H -0.0590 0.1490 0.1441 0.095 Uiso 1 1 calc R U C21 C 0.4745(5) 0.4339(3) 0.3865(2) 0.0764(13) Uani 1 1 d . . H21 H 0.5582 0.4169 0.4092 0.092 Uiso 1 1 calc R U C18 C 0.2409(5) 0.6081(3) 0.1799(2) 0.0736(12) Uani 1 1 d . . H18 H 0.3098 0.6160 0.2148 0.088 Uiso 1 1 calc R U C16 C 0.0729(5) 0.6696(3) 0.0993(3) 0.0843(14) Uani 1 1 d . . H16 H 0.0294 0.7189 0.0788 0.101 Uiso 1 1 calc R U C9 C 0.7060(5) 0.4096(3) 0.0856(2) 0.0741(12) Uani 1 1 d . . H9 H 0.7907 0.4068 0.0644 0.089 Uiso 1 1 calc R U C2 C 0.5527(5) 0.1420(3) 0.1398(3) 0.0747(12) Uani 1 1 d . . H2 H 0.5055 0.1627 0.1001 0.090 Uiso 1 1 calc R U C29 C -0.0061(4) 0.2444(3) 0.2112(3) 0.0758(13) Uani 1 1 d . . H29 H -0.0741 0.2309 0.2419 0.091 Uiso 1 1 calc R U C22 C 0.3709(5) 0.4712(3) 0.4227(2) 0.0770(13) Uani 1 1 d . . H22 H 0.3840 0.4785 0.4699 0.092 Uiso 1 1 calc R U C17 C 0.1750(5) 0.6810(3) 0.1501(3) 0.0852(14) Uani 1 1 d . . H17 H 0.2002 0.7380 0.1645 0.102 Uiso 1 1 calc R U C27 C 0.0999(5) 0.2163(3) 0.1062(3) 0.0817(14) Uani 1 1 d . . H27 H 0.1033 0.1836 0.0658 0.098 Uiso 1 1 calc R U C15 C 0.0349(5) 0.5869(3) 0.0788(3) 0.0819(14) Uani 1 1 d . . H15 H -0.0357 0.5797 0.0447 0.098 Uiso 1 1 calc R U C4 C 0.6792(6) 0.0302(4) 0.1991(5) 0.110(2) Uani 1 1 d . . H4 H 0.7192 -0.0261 0.1997 0.132 Uiso 1 1 calc R U C6 C 0.6301(5) 0.1655(4) 0.2564(3) 0.0801(13) Uani 1 1 d . . H6 H 0.6372 0.2016 0.2951 0.096 Uiso 1 1 calc R U C5 C 0.6889(6) 0.0807(5) 0.2568(4) 0.107(2) Uani 1 1 d . . H5 H 0.7346 0.0588 0.2965 0.129 Uiso 1 1 calc R U C3 C 0.6130(5) 0.0598(4) 0.1408(4) 0.0937(17) Uani 1 1 d . . H3 H 0.6084 0.0246 0.1016 0.112 Uiso 1 1 calc R U S1 S 0.68729(16) 0.79325(12) 0.06770(9) 0.1026(5) Uani 1 1 d . . O3 O 0.7278(6) 0.8205(3) 0.1363(2) 0.153(2) Uani 1 1 d . . O4 O 0.6800(6) 0.8647(3) 0.0176(2) 0.1515(19) Uani 1 1 d . . O2 O 0.7480(6) 0.7105(4) 0.0457(3) 0.166(2) Uani 1 1 d . . C31 C 0.5128(8) 0.7663(5) 0.0719(4) 0.121(2) Uani 1 1 d . . F1 F 0.5043(6) 0.7011(3) 0.1215(3) 0.180(2) Uani 1 1 d . . F3 F 0.4404(5) 0.8343(4) 0.0931(3) 0.197(2) Uani 1 1 d . . F2 F 0.4575(6) 0.7354(5) 0.0163(3) 0.238(3) Uani 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 P1 0.0483(5) 0.0516(6) 0.0613(7) -0.0044(5) -0.0002(4) 0.0009(4) O1 0.0636(17) 0.0572(17) 0.0788(19) 0.0088(14) 0.0191(14) 0.0089(14) C7 0.054(2) 0.056(2) 0.052(2) -0.0038(18) 0.0040(17) -0.0039(19) C12 0.052(2) 0.056(2) 0.058(2) -0.0044(19) -0.0010(17) -0.0035(18) C13 0.052(2) 0.053(2) 0.068(3) -0.0053(19) 0.0009(19) 0.0005(18) C25 0.048(2) 0.053(2) 0.062(2) -0.0001(19) -0.0018(18) 0.0007(17) C8 0.053(2) 0.066(3) 0.076(3) -0.005(2) 0.008(2) -0.001(2) C24 0.055(2) 0.079(3) 0.069(3) -0.016(2) -0.004(2) 0.012(2) C20 0.055(2) 0.063(3) 0.072(3) -0.010(2) -0.006(2) 0.0035(19) C10 0.072(3) 0.070(3) 0.082(3) 0.007(2) 0.013(2) -0.011(2) C1 0.047(2) 0.059(2) 0.078(3) 0.005(2) 0.009(2) 0.0023(18) C19 0.053(2) 0.054(2) 0.062(2) -0.0086(19) -0.0040(18) -0.0022(18) C14 0.066(3) 0.065(3) 0.074(3) -0.005(2) -0.012(2) 0.003(2) C23 0.070(3) 0.091(3) 0.069(3) -0.025(3) 0.004(2) 0.007(2) C30 0.060(2) 0.073(3) 0.065(3) -0.001(2) 0.000(2) -0.006(2) C11 0.063(2) 0.059(3) 0.073(3) 0.005(2) 0.005(2) -0.002(2) C26 0.058(2) 0.067(3) 0.077(3) -0.016(2) 0.009(2) -0.006(2) C28 0.063(3) 0.063(3) 0.108(4) 0.000(3) -0.014(3) -0.011(2) C21 0.073(3) 0.081(3) 0.073(3) -0.011(3) -0.019(2) 0.006(2) C18 0.068(3) 0.060(3) 0.091(3) -0.004(2) -0.014(2) 0.003(2) C16 0.076(3) 0.069(3) 0.107(4) 0.013(3) 0.002(3) 0.017(3) C9 0.063(3) 0.083(3) 0.078(3) -0.003(3) 0.020(2) -0.013(2) C2 0.071(3) 0.072(3) 0.081(3) -0.005(3) 0.005(2) -0.003(2) C29 0.057(3) 0.080(3) 0.089(3) 0.009(3) 0.003(2) -0.012(2) C22 0.081(3) 0.083(3) 0.066(3) -0.016(2) -0.008(2) -0.001(3) C17 0.079(3) 0.056(3) 0.120(4) -0.001(3) 0.001(3) 0.007(2) C27 0.077(3) 0.070(3) 0.098(4) -0.027(3) -0.001(3) -0.006(2) C15 0.075(3) 0.085(4) 0.084(3) 0.006(3) -0.015(2) 0.011(3) C4 0.071(3) 0.074(4) 0.188(8) 0.016(5) 0.028(4) 0.014(3) C6 0.065(3) 0.093(4) 0.083(3) 0.009(3) 0.001(2) 0.003(3) C5 0.082(4) 0.109(5) 0.130(5) 0.046(4) -0.004(4) 0.020(3) C3 0.073(3) 0.069(3) 0.141(5) -0.020(3) 0.027(3) -0.001(3) S1 0.0888(10) 0.1128(12) 0.1057(12) 0.0174(9) -0.0008(8) -0.0071(9) O3 0.183(5) 0.159(4) 0.109(3) 0.018(3) -0.060(3) -0.066(4) O4 0.215(5) 0.122(4) 0.118(3) 0.064(3) 0.018(3) -0.043(3) O2 0.162(5) 0.150(4) 0.193(5) 0.032(4) 0.079(4) 0.076(4) C31 0.130(6) 0.127(6) 0.107(5) -0.020(4) 0.013(4) -0.012(5) F1 0.243(5) 0.142(3) 0.162(4) 0.015(3) 0.078(4) -0.082(4) F3 0.141(4) 0.180(5) 0.277(6) 0.014(4) 0.067(4) 0.069(3) F2 0.224(6) 0.336(8) 0.145(4) -0.024(5) -0.065(4) -0.148(6) 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 '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 C25 P1 C12 111.26(18) C25 P1 C19 110.99(19) C12 P1 C19 111.20(18) C25 P1 C13 107.46(17) C12 P1 C13 107.96(18) C19 P1 C13 107.78(18) C7 O1 C1 118.9(3) O1 C7 C8 123.6(4) O1 C7 C12 116.4(3) C8 C7 C12 120.0(4) C11 C12 C7 118.5(4) C11 C12 P1 119.3(3) C7 C12 P1 122.2(3) C14 C13 C18 118.7(4) C14 C13 P1 120.8(3) C18 C13 P1 120.5(3) C26 C25 C30 119.2(4) C26 C25 P1 120.8(3) C30 C25 P1 119.8(3) C9 C8 C7 119.6(4) C23 C24 C19 120.3(4) C21 C20 C19 119.5(4) C9 C10 C11 118.7(4) C6 C1 C2 121.8(4) C6 C1 O1 117.6(4) C2 C1 O1 120.6(4) C20 C19 C24 119.1(4) C20 C19 P1 121.6(3) C24 C19 P1 119.2(3) C13 C14 C15 120.0(4) C22 C23 C24 120.2(4) C29 C30 C25 119.8(4) C10 C11 C12 121.2(4) C27 C26 C25 120.1(4) C29 C28 C27 120.7(4) C22 C21 C20 120.4(4) C17 C18 C13 120.3(4) C15 C16 C17 120.1(5) C8 C9 C10 121.9(4) C1 C2 C3 119.6(5) C28 C29 C30 120.1(4) C23 C22 C21 120.5(4) C16 C17 C18 120.0(5) C28 C27 C26 120.1(4) C16 C15 C14 120.9(4) C3 C4 C5 121.5(6) C1 C6 C5 117.7(5) C4 C5 C6 119.8(6) C4 C3 C2 119.5(6) O3 S1 O2 115.5(4) O3 S1 O4 114.7(3) O2 S1 O4 116.3(3) O3 S1 C31 103.8(3) O2 S1 C31 102.5(4) O4 S1 C31 101.2(4) F2 C31 F3 110.5(8) F2 C31 F1 107.5(7) F3 C31 F1 106.3(6) F2 C31 S1 114.1(6) F3 C31 S1 111.1(5) F1 C31 S1 107.0(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance P1 C25 1.784(4) P1 C12 1.791(4) P1 C19 1.790(4) P1 C13 1.788(4) O1 C7 1.364(4) O1 C1 1.409(5) C7 C8 1.383(5) C7 C12 1.393(5) C12 C11 1.395(5) C13 C14 1.381(5) C13 C18 1.385(6) C25 C26 1.376(5) C25 C30 1.398(5) C8 C9 1.365(6) C24 C23 1.372(6) C24 C19 1.385(5) C20 C21 1.379(6) C20 C19 1.390(5) C10 C9 1.367(6) C10 C11 1.374(6) C1 C6 1.359(6) C1 C2 1.365(6) C14 C15 1.377(6) C23 C22 1.357(6) C30 C29 1.380(6) C26 C27 1.380(6) C28 C29 1.358(7) C28 C27 1.370(7) C21 C22 1.367(6) C18 C17 1.380(6) C16 C15 1.351(7) C16 C17 1.365(7) C2 C3 1.364(7) C4 C3 1.348(8) C4 C5 1.357(9) C6 C5 1.394(8) S1 O3 1.434(4) S1 O2 1.449(5) S1 O4 1.452(4) S1 C31 1.725(8) C31 F2 1.269(7) C31 F3 1.315(8) C31 F1 1.383(8)