#------------------------------------------------------------------------------ #$Date: 2026-05-29 00:31:41 +0100 (Fri, 29 May 2026) $ #$Revision: 306115 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577307.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_1577307 loop_ _publ_author_name 'Fidelius, Jannis' 'Taube, Clemens' 'Schwedtmann, Kai' 'Hennersdorf, Felix' 'Gomila, Rosa Maria' 'Frontera, Antonio' 'Wolf, Robert' 'Weigand, Jan J.' _publ_section_title ; Imidazoliumyl-Substituted Di-and Iso-Tetraphosphanes and Their Metal-Mediated Fragmentation Reactions ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC02577C _journal_year 2026 _chemical_formula_moiety 'C34 H50 N4 P2, 2(C F3 O3 S)' _chemical_formula_sum 'C36 H50 F6 N4 O6 P2 S2' _chemical_formula_weight 874.86 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2026-01-11 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2026-01-21 deposited with the CCDC. 2026-05-28 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 99.1657(6) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 7.96005(6) _cell_length_b 12.02181(9) _cell_length_c 22.34595(15) _cell_measurement_reflns_used 8100 _cell_measurement_temperature 200.00(10) _cell_measurement_theta_max 76.3570 _cell_measurement_theta_min 4.0040 _cell_volume 2111.07(3) _computing_cell_refinement 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 200.00(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2850 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 18.00 58.00 0.50 2.00 -- 42.75 -99.00 90.00 80 2 \w 52.00 87.00 0.50 8.00 -- 111.00 -94.00 60.00 70 3 \w 58.00 98.00 0.50 8.00 -- 111.00 -94.00 0.00 80 4 \w 56.00 131.00 0.50 8.00 -- 111.00 -30.00 60.00 150 5 \w 88.00 134.00 0.50 8.00 -- 111.00 61.00 -60.00 92 6 \w 129.00 163.00 0.50 8.00 -- 111.00 61.00 -90.00 68 7 \w 84.00 113.00 0.50 8.00 -- 111.00 61.00 -90.00 58 8 \w 36.00 135.00 0.50 8.00 -- 111.00 -30.00 -30.00 198 9 \w 43.00 91.00 0.50 8.00 -- 111.00 -94.00-120.00 96 10 \w 42.00 108.00 0.50 8.00 -- 111.00 -94.00-150.00 132 11 \w 27.00 97.00 0.50 2.00 -- 42.75-125.00 -60.00 140 12 \w 4.00 53.00 0.50 2.00 -- 42.75 -99.00-180.00 98 13 \w -107.00 -20.00 0.50 2.00 -- -38.50 -38.00-120.00 174 14 \w 143.00 170.00 0.50 8.00 -- 111.00 125.00 150.00 54 15 \w 110.00 137.00 0.50 8.00 -- 111.00 125.00 150.00 54 16 \w 100.00 177.00 0.50 8.00 -- 111.00 125.00 90.00 154 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0235378000 _diffrn_orient_matrix_UB_12 -0.1148237000 _diffrn_orient_matrix_UB_13 -0.0308331000 _diffrn_orient_matrix_UB_21 -0.1359194000 _diffrn_orient_matrix_UB_22 -0.0298674000 _diffrn_orient_matrix_UB_23 0.0393155000 _diffrn_orient_matrix_UB_31 -0.1392567000 _diffrn_orient_matrix_UB_32 0.0484715000 _diffrn_orient_matrix_UB_33 -0.0487835000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0120 _diffrn_reflns_av_unetI/netI 0.0129 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.987 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 11092 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.987 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.564 _diffrn_reflns_theta_min 4.008 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.508 _exptl_absorpt_correction_T_max 0.791 _exptl_absorpt_correction_T_min 0.651 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.376 _exptl_crystal_description block _exptl_crystal_F_000 916 _exptl_crystal_size_max 0.252 _exptl_crystal_size_mid 0.176 _exptl_crystal_size_min 0.112 _refine_diff_density_max 0.524 _refine_diff_density_min -0.318 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 332 _refine_ls_number_reflns 4372 _refine_ls_number_restraints 253 _refine_ls_restrained_S_all 1.145 _refine_ls_R_factor_all 0.0395 _refine_ls_R_factor_gt 0.0385 _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^)+(0.0609P)^2^+0.8365P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1056 _refine_ls_wR_factor_ref 0.1066 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4204 _reflns_number_total 4372 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc02577c2.cif _cod_data_source_block jjw0986 _cod_original_cell_volume 2111.08(3) _cod_database_code 1577307 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C72 H100 F12 N8 O12 P4 S4 ' _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. ; _reflns_odcompleteness_completeness 99.97 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2. Uiso/Uaniso restraints and constraints S1A \\sim F1A \\sim F2A \\sim F3A \\sim O1A \\sim O2A \\sim O3A \\sim C18A \\sim S1B \\sim F1B \\sim F2B \\sim F3B \\sim O1B \\sim O2B \\sim O3B \\sim C18B: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A 3. Same fragment restrains {S1B, F1B, F2B, F3B, O2B, O3B, O1B, C18B} sigma for 1-2: 0.02, 1-3: 0.02 as in {S1A, F1A, F2A, F3A, O1A, O2A, O3A, C18A} 4. Others Sof(S1B)=Sof(F1B)=Sof(F2B)=Sof(F3B)=Sof(O2B)=Sof(O3B)=Sof(O1B)=Sof(C18B)=1- FVAR(1) Sof(S1A)=Sof(F1A)=Sof(F2A)=Sof(F3A)=Sof(O1A)=Sof(O2A)=Sof(O3A)=Sof(C18A)= FVAR(1) 5.a Ternary CH refined with riding coordinates: C4(H4), C7(H7) 5.b Aromatic/amide H refined with riding coordinates: C13(H13), C14(H14), C15(H15), C16(H16), C17(H17) 5.c Idealised Me refined as rotating group: C5(H5A,H5B,H5C), C6(H6A,H6B,H6C), C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C10(H10A, H10B,H10C), C11(H11A,H11B,H11C) ; _shelx_res_file ; TITL jjw0986_a.res in P2(1)/c jjw0986.res created by SHELXL-2018/3 at 20:23:35 on 11-Jan-2026 REM Old TITL jjw0986 in P21/c #14 REM SHELXT solution in P2(1)/c REM R1 0.194, Rweak 0.025, Alpha 0.059, Orientation as input REM Formula found by SHELXT: C18 N2 O3 F3 S2 CELL 1.54184 7.960051 12.021811 22.345949 90 99.1657 90 ZERR 2 0.00006 0.000092 0.000151 0 0.0006 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O P S UNIT 72 100 12 8 12 4 4 SIMU 0.01 0.02 2 S1A > F3B O1B O2B O3B C18B L.S. 10 PLAN 4 TEMP 100 CONF BOND $H LIST 4 MORE -1 fmap 2 acta REM REM REM WGHT 0.060900 0.836500 FVAR 0.49990 0.51459 P1 6 0.372275 0.471865 0.475257 11.00000 0.03541 0.02407 = 0.02028 -0.00029 -0.00196 0.00260 N1 4 0.571341 0.333227 0.405698 11.00000 0.03746 0.02667 = 0.02676 -0.00371 0.00033 0.00095 N2 4 0.377307 0.436896 0.352817 11.00000 0.03913 0.02946 = 0.02147 -0.00011 -0.00198 -0.00292 C1 1 0.443814 0.406427 0.410025 11.00000 0.03605 0.02365 = 0.02242 -0.00048 -0.00153 -0.00144 C2 1 0.584639 0.318020 0.345271 11.00000 0.04607 0.03825 = 0.02995 -0.00955 0.00608 -0.00352 C3 1 0.462419 0.382690 0.312605 11.00000 0.04809 0.03980 = 0.02461 -0.00569 0.00387 -0.00708 C4 1 0.676595 0.277758 0.458580 11.00000 0.04125 0.03022 = 0.03451 0.00113 -0.00057 0.00785 AFIX 13 H4 2 0.630276 0.300629 0.494767 11.00000 -1.20000 AFIX 0 C5 1 0.662214 0.151246 0.454803 11.00000 0.06849 0.03015 = 0.06612 0.00355 0.00888 0.01371 AFIX 137 H5A 2 0.545751 0.130737 0.441378 11.00000 -1.50000 H5B 2 0.700377 0.119674 0.494076 11.00000 -1.50000 H5C 2 0.731469 0.123766 0.426578 11.00000 -1.50000 AFIX 0 C6 1 0.860430 0.317387 0.467037 11.00000 0.03910 0.05380 = 0.04563 -0.00321 -0.00066 0.00891 AFIX 137 H6A 2 0.915003 0.288205 0.435051 11.00000 -1.50000 H6B 2 0.919295 0.291763 0.505407 11.00000 -1.50000 H6C 2 0.862960 0.397195 0.465990 11.00000 -1.50000 AFIX 0 C7 1 0.227862 0.511001 0.332472 11.00000 0.04416 0.03694 = 0.02520 0.00569 -0.00750 0.00150 AFIX 13 H7 2 0.207034 0.507135 0.288101 11.00000 -1.20000 AFIX 0 C8 1 0.265414 0.632112 0.348326 11.00000 0.06602 0.03402 = 0.04987 0.01173 -0.01269 0.00282 AFIX 137 H8A 2 0.273563 0.642116 0.391314 11.00000 -1.50000 H8B 2 0.175383 0.677819 0.327772 11.00000 -1.50000 H8C 2 0.371061 0.653049 0.335925 11.00000 -1.50000 AFIX 0 C9 1 0.068290 0.466949 0.353148 11.00000 0.04128 0.05226 = 0.04747 0.01022 -0.00407 0.00248 AFIX 137 H9A 2 0.055899 0.389247 0.343546 11.00000 -1.50000 H9B 2 -0.028895 0.506775 0.332852 11.00000 -1.50000 H9C 2 0.076730 0.476905 0.396149 11.00000 -1.50000 AFIX 0 C10 1 0.703844 0.240026 0.321431 11.00000 0.06052 0.05974 = 0.04809 -0.02078 0.01165 0.00708 AFIX 137 H10A 2 0.808539 0.236179 0.349412 11.00000 -1.50000 H10B 2 0.726321 0.266310 0.282917 11.00000 -1.50000 H10C 2 0.653402 0.167387 0.316619 11.00000 -1.50000 AFIX 0 C11 1 0.415204 0.390868 0.245417 11.00000 0.07056 0.06647 = 0.02390 -0.00462 0.00425 -0.00437 AFIX 137 H11A 2 0.301181 0.364079 0.233466 11.00000 -1.50000 H11B 2 0.492208 0.346713 0.226377 11.00000 -1.50000 H11C 2 0.421837 0.467074 0.233170 11.00000 -1.50000 AFIX 0 C12 1 0.323227 0.354101 0.521509 11.00000 0.03132 0.02988 = 0.02507 0.00232 -0.00210 0.00082 C13 1 0.292193 0.247698 0.497511 11.00000 0.04162 0.03169 = 0.02996 -0.00016 0.00002 0.00020 AFIX 43 H13 2 0.306024 0.233196 0.457706 11.00000 -1.20000 AFIX 0 C14 1 0.240715 0.163419 0.532909 11.00000 0.05427 0.02977 = 0.04510 0.00325 0.00111 -0.00375 AFIX 43 H14 2 0.221327 0.092384 0.516805 11.00000 -1.20000 AFIX 0 C15 1 0.217953 0.184207 0.592052 11.00000 0.05395 0.04224 = 0.04011 0.01495 0.00281 -0.00539 AFIX 43 H15 2 0.185568 0.126964 0.615787 11.00000 -1.20000 AFIX 0 C16 1 0.243455 0.290174 0.615725 11.00000 0.05020 0.04991 = 0.02804 0.00664 0.00434 -0.00298 AFIX 43 H16 2 0.226286 0.304577 0.655193 11.00000 -1.20000 AFIX 0 C17 1 0.294570 0.374926 0.580696 11.00000 0.04233 0.03643 = 0.02755 -0.00103 0.00153 -0.00216 AFIX 43 H17 2 0.310002 0.446332 0.596636 11.00000 -1.20000 AFIX 0 SAME 0.02 0.02 S1B F1B F2B F3B O2B O3B O1B C18B PART 1 S1A 7 0.195388 0.121733 0.304196 21.00000 0.04292 0.04028 = 0.03536 -0.00657 0.00180 -0.00419 F1A 3 0.056284 0.005712 0.377407 21.00000 0.17279 0.12009 = 0.17919 0.00557 0.10878 -0.06377 F2A 3 0.300875 -0.048109 0.371021 21.00000 0.16684 0.11898 = 0.12457 0.08134 -0.01260 0.01014 F3A 3 0.101190 -0.087486 0.299332 21.00000 0.17667 0.05502 = 0.12728 -0.01950 -0.02946 -0.03183 O1A 5 0.251785 0.191681 0.353599 21.00000 0.12399 0.07994 = 0.03836 -0.00005 -0.01679 -0.06558 O2A 5 0.037074 0.144781 0.268770 21.00000 0.09174 0.09296 = 0.08787 -0.02662 -0.04253 0.03055 O3A 5 0.325362 0.100688 0.267908 21.00000 0.08599 0.07800 = 0.10116 0.02075 0.04949 0.01947 C18A 1 0.161813 -0.007171 0.337409 21.00000 0.09956 0.06428 = 0.06374 0.00482 0.01031 -0.02304 PART 2 S1B 7 0.169985 0.105263 0.307914 -21.00000 0.10578 0.04176 = 0.04680 -0.01279 -0.03144 0.01174 F1B 3 0.380692 -0.029971 0.369918 -21.00000 0.08895 0.13652 = 0.09809 0.02247 -0.00547 0.05382 F2B 3 0.176877 -0.105579 0.316329 -21.00000 0.15440 0.04155 = 0.14020 -0.01469 -0.00583 -0.00715 F3B 3 0.137511 -0.024456 0.397506 -21.00000 0.14846 0.10455 = 0.08063 0.02361 0.04624 -0.03012 O2B 5 0.206002 0.192395 0.351888 -21.00000 0.12471 0.04799 = 0.05744 -0.02497 -0.01732 -0.00158 O3B 5 -0.007254 0.095617 0.288853 -21.00000 0.08483 0.14993 = 0.11633 -0.08033 -0.04791 0.06377 O1B 5 0.268319 0.095664 0.260374 -21.00000 0.13683 0.11324 = 0.03515 0.01224 0.01659 -0.01240 C18B 1 0.216136 -0.018951 0.350942 -21.00000 0.08569 0.04343 = 0.06267 0.01051 0.00635 -0.00291 HKLF 4 REM jjw0986_a.res in P2(1)/c REM wR2 = 0.1066, GooF = S = 1.026, Restrained GooF = 1.145 for all data REM R1 = 0.0385 for 4204 Fo > 4sig(Fo) and 0.0395 for all 4372 data REM 332 parameters refined using 253 restraints END WGHT 0.0609 0.8366 REM Highest difference peak 0.524, deepest hole -0.318, 1-sigma level 0.050 Q1 1 -0.0523 0.0128 0.3237 11.00000 0.05 0.52 Q2 1 0.1392 0.1329 0.2548 11.00000 0.05 0.37 Q3 1 0.4139 0.0425 0.3443 11.00000 0.05 0.27 Q4 1 0.3924 0.0853 0.3129 11.00000 0.05 0.22 ; _shelx_res_checksum 9708 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.125 _oxdiff_exptl_absorpt_empirical_full_min 0.882 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.37227(4) 0.47186(3) 0.47526(2) 0.02728(11) Uani 1 1 d . . . . . N1 N 0.57134(15) 0.33323(10) 0.40570(5) 0.0308(3) Uani 1 1 d . . . . . N2 N 0.37731(15) 0.43690(10) 0.35282(5) 0.0308(3) Uani 1 1 d . . . . . C1 C 0.44381(17) 0.40643(11) 0.41002(6) 0.0280(3) Uani 1 1 d . . . . . C2 C 0.5846(2) 0.31802(13) 0.34527(7) 0.0381(3) Uani 1 1 d . . . . . C3 C 0.4624(2) 0.38269(14) 0.31261(6) 0.0377(3) Uani 1 1 d . . . . . C4 C 0.6766(2) 0.27776(13) 0.45858(7) 0.0360(3) Uani 1 1 d . . . . . H4 H 0.630276 0.300629 0.494767 0.043 Uiso 1 1 calc R U . . . C5 C 0.6622(3) 0.15125(15) 0.45480(10) 0.0551(5) Uani 1 1 d . . . . . H5A H 0.545751 0.130737 0.441378 0.083 Uiso 1 1 calc R U . . . H5B H 0.700377 0.119674 0.494076 0.083 Uiso 1 1 calc R U . . . H5C H 0.731469 0.123766 0.426578 0.083 Uiso 1 1 calc R U . . . C6 C 0.8604(2) 0.31739(17) 0.46704(8) 0.0470(4) Uani 1 1 d . . . . . H6A H 0.915003 0.288205 0.435051 0.070 Uiso 1 1 calc R U . . . H6B H 0.919295 0.291763 0.505407 0.070 Uiso 1 1 calc R U . . . H6C H 0.862960 0.397195 0.465990 0.070 Uiso 1 1 calc R U . . . C7 C 0.2279(2) 0.51100(13) 0.33247(7) 0.0369(3) Uani 1 1 d . . . . . H7 H 0.207034 0.507135 0.288101 0.044 Uiso 1 1 calc R U . . . C8 C 0.2654(3) 0.63211(15) 0.34833(9) 0.0524(5) Uani 1 1 d . . . . . H8A H 0.273563 0.642116 0.391314 0.079 Uiso 1 1 calc R U . . . H8B H 0.175383 0.677819 0.327772 0.079 Uiso 1 1 calc R U . . . H8C H 0.371061 0.653049 0.335925 0.079 Uiso 1 1 calc R U . . . C9 C 0.0683(2) 0.46695(16) 0.35315(9) 0.0482(4) Uani 1 1 d . . . . . H9A H 0.055899 0.389247 0.343546 0.072 Uiso 1 1 calc R U . . . H9B H -0.028895 0.506775 0.332852 0.072 Uiso 1 1 calc R U . . . H9C H 0.076730 0.476905 0.396149 0.072 Uiso 1 1 calc R U . . . C10 C 0.7038(3) 0.24003(18) 0.32143(9) 0.0558(5) Uani 1 1 d . . . . . H10A H 0.808539 0.236179 0.349412 0.084 Uiso 1 1 calc R U . . . H10B H 0.726321 0.266310 0.282917 0.084 Uiso 1 1 calc R U . . . H10C H 0.653402 0.167387 0.316619 0.084 Uiso 1 1 calc R U . . . C11 C 0.4152(3) 0.39087(19) 0.24542(7) 0.0540(5) Uani 1 1 d . . . . . H11A H 0.301181 0.364079 0.233466 0.081 Uiso 1 1 calc R U . . . H11B H 0.492208 0.346713 0.226377 0.081 Uiso 1 1 calc R U . . . H11C H 0.421837 0.467074 0.233170 0.081 Uiso 1 1 calc R U . . . C12 C 0.32323(17) 0.35410(12) 0.52151(6) 0.0295(3) Uani 1 1 d . . . . . C13 C 0.29219(19) 0.24770(13) 0.49751(7) 0.0350(3) Uani 1 1 d . . . . . H13 H 0.306024 0.233196 0.457706 0.042 Uiso 1 1 calc R U . . . C14 C 0.2407(2) 0.16342(14) 0.53291(8) 0.0438(4) Uani 1 1 d . . . . . H14 H 0.221327 0.092384 0.516805 0.053 Uiso 1 1 calc R U . . . C15 C 0.2180(2) 0.18421(15) 0.59205(8) 0.0459(4) Uani 1 1 d . . . . . H15 H 0.185568 0.126964 0.615787 0.055 Uiso 1 1 calc R U . . . C16 C 0.2435(2) 0.29017(15) 0.61572(7) 0.0429(4) Uani 1 1 d . . . . . H16 H 0.226286 0.304577 0.655193 0.052 Uiso 1 1 calc R U . . . C17 C 0.29457(19) 0.37493(13) 0.58070(6) 0.0359(3) Uani 1 1 d . . . . . H17 H 0.310002 0.446332 0.596636 0.043 Uiso 1 1 calc R U . . . S1A S 0.1954(3) 0.1217(3) 0.30420(15) 0.0400(5) Uani 0.515(9) 1 d D U P A 1 F1A F 0.0563(13) 0.0057(7) 0.3774(4) 0.149(3) Uani 0.515(9) 1 d D U P A 1 F2A F 0.3009(14) -0.0481(6) 0.3710(4) 0.141(3) Uani 0.515(9) 1 d D U P A 1 F3A F 0.1012(12) -0.0875(5) 0.2993(3) 0.126(2) Uani 0.515(9) 1 d D U P A 1 O1A O 0.2518(12) 0.1917(6) 0.3536(3) 0.084(2) Uani 0.515(9) 1 d D U P A 1 O2A O 0.0371(9) 0.1448(6) 0.2688(3) 0.097(2) Uani 0.515(9) 1 d D U P A 1 O3A O 0.3254(9) 0.1007(7) 0.2679(4) 0.085(2) Uani 0.515(9) 1 d D U P A 1 C18A C 0.1618(12) -0.0072(6) 0.3374(4) 0.0762(18) Uani 0.515(9) 1 d D U P A 1 S1B S 0.1700(7) 0.1053(4) 0.30791(19) 0.0695(9) Uani 0.485(9) 1 d D U P A 2 F1B F 0.3807(8) -0.0300(7) 0.3699(3) 0.110(2) Uani 0.485(9) 1 d D U P A 2 F2B F 0.1769(11) -0.1056(5) 0.3163(4) 0.115(2) Uani 0.485(9) 1 d D U P A 2 F3B F 0.1375(11) -0.0245(6) 0.3975(3) 0.108(2) Uani 0.485(9) 1 d D U P A 2 O2B O 0.2060(14) 0.1924(6) 0.3519(4) 0.080(2) Uani 0.485(9) 1 d D U P A 2 O3B O -0.0073(9) 0.0956(9) 0.2889(4) 0.124(3) Uani 0.485(9) 1 d D U P A 2 O1B O 0.2683(12) 0.0957(9) 0.2604(3) 0.095(2) Uani 0.485(9) 1 d D U P A 2 C18B C 0.2161(11) -0.0190(5) 0.3509(4) 0.0645(16) Uani 0.485(9) 1 d D U P A 2 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 0.0354(2) 0.02407(18) 0.02028(17) -0.00029(11) -0.00196(13) 0.00260(12) N1 0.0375(6) 0.0267(6) 0.0268(6) -0.0037(4) 0.0003(4) 0.0009(5) N2 0.0391(6) 0.0295(6) 0.0215(5) -0.0001(4) -0.0020(4) -0.0029(5) C1 0.0360(7) 0.0237(6) 0.0224(6) -0.0005(5) -0.0015(5) -0.0014(5) C2 0.0461(8) 0.0383(8) 0.0300(7) -0.0095(6) 0.0061(6) -0.0035(6) C3 0.0481(8) 0.0398(8) 0.0246(7) -0.0057(6) 0.0039(6) -0.0071(6) C4 0.0413(8) 0.0302(7) 0.0345(7) 0.0011(6) -0.0006(6) 0.0078(6) C5 0.0685(12) 0.0301(8) 0.0661(12) 0.0036(8) 0.0089(9) 0.0137(8) C6 0.0391(8) 0.0538(10) 0.0456(9) -0.0032(8) -0.0007(7) 0.0089(7) C7 0.0442(8) 0.0369(8) 0.0252(7) 0.0057(6) -0.0075(6) 0.0015(6) C8 0.0660(11) 0.0340(8) 0.0499(10) 0.0117(7) -0.0127(8) 0.0028(8) C9 0.0413(9) 0.0523(10) 0.0475(9) 0.0102(8) -0.0041(7) 0.0025(7) C10 0.0605(11) 0.0597(12) 0.0481(10) -0.0208(9) 0.0117(8) 0.0071(9) C11 0.0706(12) 0.0665(12) 0.0239(7) -0.0046(7) 0.0042(7) -0.0044(9) C12 0.0313(6) 0.0299(7) 0.0251(6) 0.0023(5) -0.0021(5) 0.0008(5) C13 0.0416(7) 0.0317(7) 0.0300(7) -0.0002(6) 0.0000(6) 0.0002(6) C14 0.0543(9) 0.0298(7) 0.0451(9) 0.0032(6) 0.0011(7) -0.0037(7) C15 0.0539(9) 0.0422(9) 0.0401(8) 0.0150(7) 0.0028(7) -0.0054(7) C16 0.0502(9) 0.0499(9) 0.0280(7) 0.0066(7) 0.0043(6) -0.0030(7) C17 0.0423(8) 0.0364(8) 0.0275(7) -0.0010(6) 0.0015(6) -0.0022(6) S1A 0.0429(7) 0.0403(10) 0.0354(7) -0.0066(6) 0.0018(5) -0.0042(5) F1A 0.173(6) 0.120(5) 0.179(6) 0.006(4) 0.109(5) -0.064(4) F2A 0.167(6) 0.119(4) 0.125(4) 0.081(3) -0.013(5) 0.010(5) F3A 0.177(6) 0.055(3) 0.127(4) -0.019(3) -0.029(4) -0.032(3) O1A 0.124(5) 0.080(4) 0.038(2) 0.000(2) -0.017(2) -0.066(3) O2A 0.092(3) 0.093(4) 0.088(3) -0.027(3) -0.043(3) 0.031(3) O3A 0.086(3) 0.078(3) 0.101(5) 0.021(3) 0.049(3) 0.019(3) C18A 0.100(4) 0.064(3) 0.064(3) 0.005(2) 0.010(3) -0.023(3) S1B 0.106(2) 0.0418(11) 0.0468(13) -0.0128(8) -0.0314(13) 0.0117(13) F1B 0.089(3) 0.137(5) 0.098(3) 0.022(3) -0.005(3) 0.054(3) F2B 0.154(5) 0.042(2) 0.140(5) -0.015(3) -0.006(4) -0.007(3) F3B 0.148(5) 0.105(4) 0.081(3) 0.024(2) 0.046(3) -0.030(3) O2B 0.125(6) 0.048(3) 0.057(3) -0.025(2) -0.017(3) -0.002(3) O3B 0.085(4) 0.150(6) 0.116(5) -0.080(4) -0.048(3) 0.064(4) O1B 0.137(6) 0.113(4) 0.035(2) 0.012(2) 0.017(3) -0.012(4) C18B 0.086(4) 0.043(2) 0.063(4) 0.011(2) 0.006(3) -0.003(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' F F 0.0727 0.0534 '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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0561 0 0 -1 0.0561 0 -1 -1 0.0828 0 1 1 0.0828 0 -1 1 0.0827 0 1 -1 0.0827 -1 0 1 0.0985 5 0 -7 0.0814 -2 7 1 0.0551 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 P1 P1 98.57(5) . 3_666 ? C1 P1 C12 103.84(6) . . ? C12 P1 P1 102.21(5) . 3_666 ? C1 N1 C2 109.23(12) . . ? C1 N1 C4 124.38(12) . . ? C2 N1 C4 126.39(13) . . ? C1 N2 C3 109.27(12) . . ? C1 N2 C7 128.30(12) . . ? C3 N2 C7 122.31(12) . . ? N1 C1 P1 131.89(10) . . ? N2 C1 P1 120.84(10) . . ? N2 C1 N1 107.00(12) . . ? N1 C2 C10 125.71(15) . . ? C3 C2 N1 106.76(13) . . ? C3 C2 C10 127.43(15) . . ? N2 C3 C11 123.78(15) . . ? C2 C3 N2 107.74(12) . . ? C2 C3 C11 128.36(16) . . ? N1 C4 H4 106.9 . . ? N1 C4 C5 111.94(14) . . ? N1 C4 C6 111.46(13) . . ? C5 C4 H4 106.9 . . ? C6 C4 H4 106.9 . . ? C6 C4 C5 112.39(14) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6B 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N2 C7 H7 106.1 . . ? N2 C7 C8 112.49(13) . . ? N2 C7 C9 111.32(12) . . ? C8 C7 H7 106.1 . . ? C9 C7 H7 106.1 . . ? C9 C7 C8 114.08(16) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 P1 122.21(11) . . ? C13 C12 C17 118.82(13) . . ? C17 C12 P1 118.45(11) . . ? C12 C13 H13 120.0 . . ? C14 C13 C12 120.09(14) . . ? C14 C13 H13 120.0 . . ? C13 C14 H14 119.7 . . ? C15 C14 C13 120.52(16) . . ? C15 C14 H14 119.7 . . ? C14 C15 H15 120.1 . . ? C16 C15 C14 119.87(15) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 120.0 . . ? C15 C16 C17 120.02(15) . . ? C17 C16 H16 120.0 . . ? C12 C17 H17 119.7 . . ? C16 C17 C12 120.61(15) . . ? C16 C17 H17 119.7 . . ? O1A S1A O2A 118.1(5) . . ? O1A S1A O3A 112.4(5) . . ? O1A S1A C18A 104.3(4) . . ? O2A S1A O3A 112.3(5) . . ? O2A S1A C18A 103.2(4) . . ? O3A S1A C18A 104.8(4) . . ? F1A C18A S1A 109.6(6) . . ? F2A C18A S1A 113.3(6) . . ? F2A C18A F1A 102.8(8) . . ? F3A C18A S1A 115.8(6) . . ? F3A C18A F1A 108.2(7) . . ? F3A C18A F2A 106.2(7) . . ? O2B S1B C18B 103.9(5) . . ? O3B S1B O2B 110.4(5) . . ? O3B S1B O1B 114.2(5) . . ? O3B S1B C18B 101.8(5) . . ? O1B S1B O2B 119.9(6) . . ? O1B S1B C18B 104.2(5) . . ? F1B C18B S1B 111.5(5) . . ? F2B C18B S1B 109.8(6) . . ? F2B C18B F1B 104.0(7) . . ? F3B C18B S1B 113.0(6) . . ? F3B C18B F1B 108.6(7) . . ? F3B C18B F2B 109.5(7) . . ? 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 P1 2.2580(7) 3_666 ? P1 C1 1.8255(14) . ? P1 C12 1.8313(14) . ? N1 C1 1.3585(18) . ? N1 C2 1.3833(18) . ? N1 C4 1.4925(18) . ? N2 C1 1.3539(17) . ? N2 C3 1.3730(19) . ? N2 C7 1.4977(19) . ? C2 C3 1.363(2) . ? C2 C10 1.491(2) . ? C3 C11 1.492(2) . ? C4 H4 0.9800 . ? C4 C5 1.527(2) . ? C4 C6 1.522(2) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 H7 0.9800 . ? C7 C8 1.517(2) . ? C7 C9 1.515(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.394(2) . ? C12 C17 1.400(2) . ? C13 H13 0.9300 . ? C13 C14 1.387(2) . ? C14 H14 0.9300 . ? C14 C15 1.385(3) . ? C15 H15 0.9300 . ? C15 C16 1.382(3) . ? C16 H16 0.9300 . ? C16 C17 1.385(2) . ? C17 H17 0.9300 . ? S1A O1A 1.403(6) . ? S1A O2A 1.405(6) . ? S1A O3A 1.435(6) . ? S1A C18A 1.757(7) . ? F1A C18A 1.330(10) . ? F2A C18A 1.329(8) . ? F3A C18A 1.326(9) . ? S1B O2B 1.434(6) . ? S1B O3B 1.412(6) . ? S1B O1B 1.421(6) . ? S1B C18B 1.782(7) . ? F1B C18B 1.318(9) . ? F2B C18B 1.305(9) . ? F3B C18B 1.299(9) . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag P1 P1 C1 N1 47.70(14) 3_666 . . . ? P1 P1 C1 N2 -125.34(11) 3_666 . . . ? P1 P1 C12 C13 -122.24(12) 3_666 . . . ? P1 P1 C12 C17 66.15(12) 3_666 . . . ? P1 C12 C13 C14 -174.24(12) . . . . ? P1 C12 C17 C16 174.69(12) . . . . ? N1 C2 C3 N2 0.45(17) . . . . ? N1 C2 C3 C11 -175.59(17) . . . . ? C1 P1 C12 C13 -20.10(13) . . . . ? C1 P1 C12 C17 168.29(11) . . . . ? C1 N1 C2 C3 -0.33(17) . . . . ? C1 N1 C2 C10 -176.95(16) . . . . ? C1 N1 C4 C5 120.45(16) . . . . ? C1 N1 C4 C6 -112.70(16) . . . . ? C1 N2 C3 C2 -0.42(17) . . . . ? C1 N2 C3 C11 175.85(15) . . . . ? C1 N2 C7 C8 71.4(2) . . . . ? C1 N2 C7 C9 -58.0(2) . . . . ? C2 N1 C1 P1 -173.68(12) . . . . ? C2 N1 C1 N2 0.08(16) . . . . ? C2 N1 C4 C5 -58.5(2) . . . . ? C2 N1 C4 C6 68.38(19) . . . . ? C3 N2 C1 P1 174.80(10) . . . . ? C3 N2 C1 N1 0.21(16) . . . . ? C3 N2 C7 C8 -112.95(16) . . . . ? C3 N2 C7 C9 117.58(16) . . . . ? C4 N1 C1 P1 7.2(2) . . . . ? C4 N1 C1 N2 -179.00(12) . . . . ? C4 N1 C2 C3 178.72(14) . . . . ? C4 N1 C2 C10 2.1(3) . . . . ? C7 N2 C1 P1 -9.1(2) . . . . ? C7 N2 C1 N1 176.28(13) . . . . ? C7 N2 C3 C2 -176.77(13) . . . . ? C7 N2 C3 C11 -0.5(2) . . . . ? C10 C2 C3 N2 177.00(17) . . . . ? C10 C2 C3 C11 1.0(3) . . . . ? C12 P1 C1 N1 -57.22(15) . . . . ? C12 P1 C1 N2 129.74(11) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C13 C12 C17 C16 2.8(2) . . . . ? C13 C14 C15 C16 1.3(3) . . . . ? C14 C15 C16 C17 -1.1(3) . . . . ? C15 C16 C17 C12 -0.9(3) . . . . ? C17 C12 C13 C14 -2.7(2) . . . . ? O1A S1A C18A F1A 54.9(8) . . . . ? O1A S1A C18A F2A -59.3(9) . . . . ? O1A S1A C18A F3A 177.6(7) . . . . ? O2A S1A C18A F1A -69.1(7) . . . . ? O2A S1A C18A F2A 176.7(7) . . . . ? O2A S1A C18A F3A 53.6(8) . . . . ? O3A S1A C18A F1A 173.2(6) . . . . ? O3A S1A C18A F2A 59.0(8) . . . . ? O3A S1A C18A F3A -64.1(8) . . . . ? O2B S1B C18B F1B -69.5(8) . . . . ? O2B S1B C18B F2B 175.7(7) . . . . ? O2B S1B C18B F3B 53.1(8) . . . . ? O3B S1B C18B F1B 175.8(6) . . . . ? O3B S1B C18B F2B 61.0(7) . . . . ? O3B S1B C18B F3B -61.6(7) . . . . ? O1B S1B C18B F1B 56.7(7) . . . . ? O1B S1B C18B F2B -58.1(8) . . . . ? O1B S1B C18B F3B 179.3(7) . . . . ? loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0.0002 0.0002 0.9994 -0.0308 0.0393 -0.0488 -0.0002 -0.0002 -0.9994 0.0308 -0.0393 0.0488 0.0001 -0.9995 -0.9977 0.1455 -0.0094 0.0002 -0.0001 0.9995 0.9977 -0.1455 0.0094 -0.0002 0.0004 -0.9991 1.0011 0.0839 0.0691 -0.0973 -0.0004 0.9991 -1.0011 -0.0839 -0.0691 0.0973 -0.9994 0.0018 0.9977 -0.0074 0.1750 0.0906 4.9964 -0.0093 -6.9875 0.0989 -0.9536 -0.3554 -2.0004 6.9987 0.9844 -0.7869 0.1016 0.5698