#------------------------------------------------------------------------------ #$Date: 2026-05-29 00:31:41 +0100 (Fri, 29 May 2026) $ #$Revision: 306115 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577315.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_1577315 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_absolute_configuration ad _chemical_formula_moiety 'C17 H31 Cl N2 P, C F3 O3 S' _chemical_formula_sum 'C18 H31 Cl F3 N2 O3 P S' _chemical_formula_weight 478.93 _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 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 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.93012(14) _cell_length_b 10.76679(12) _cell_length_c 16.9595(2) _cell_measurement_reflns_used 15301 _cell_measurement_temperature 100.01(10) _cell_measurement_theta_max 76.3340 _cell_measurement_theta_min 4.8550 _cell_volume 2361.03(5) _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 100.01(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.5700 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.997 _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 -75.00 40.00 0.50 2.50 -- -38.50 19.00 120.00 230 2 \w 23.00 98.00 0.50 2.50 -- 42.50-125.00 60.00 150 3 \w 1.00 82.00 0.50 2.50 -- 42.50 -99.00 0.00 162 4 \w 37.00 142.00 0.50 10.00 -- 111.00 -77.00 150.00 210 5 \w 94.00 178.00 0.50 10.00 -- 111.00 125.00 60.00 168 6 \w 40.00 135.00 0.50 10.00 -- 111.00 -45.00-180.00 190 7 \w 94.00 178.00 0.50 10.00 -- 111.00 125.00-120.00 168 8 \w 87.00 178.00 0.50 10.00 -- 111.00 30.00-180.00 182 9 \w 30.00 109.00 0.50 10.00 -- 111.00 -94.00 120.00 158 10 \w 80.00 178.00 0.50 10.00 -- 111.00 77.00 -30.00 196 11 \w 39.00 121.00 0.50 10.00 -- 111.00-125.00 30.00 164 12 \w 41.00 139.00 0.50 10.00 -- 111.00 -61.00 120.00 196 13 \w 30.00 109.00 0.50 10.00 -- 111.00 -94.00 -30.00 158 14 \w 16.00 113.00 0.50 2.50 -- 42.50 57.00-180.00 194 15 \w 11.00 116.00 0.50 2.50 -- 42.50 77.00 60.00 210 16 \w 16.00 113.00 0.50 2.50 -- 42.50 57.00 -30.00 194 17 \w 87.00 112.00 0.50 10.00 -- 111.00 45.00 -60.00 50 18 \w 87.00 178.00 0.50 10.00 -- 111.00 30.00 60.00 182 19 \w 87.00 178.00 0.50 10.00 -- 111.00 30.00-120.00 182 ; _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 0.0237793000 _diffrn_orient_matrix_UB_12 0.0305324000 _diffrn_orient_matrix_UB_13 -0.0868254000 _diffrn_orient_matrix_UB_21 0.1057614000 _diffrn_orient_matrix_UB_22 -0.0650171000 _diffrn_orient_matrix_UB_23 0.0077042000 _diffrn_orient_matrix_UB_31 -0.0493679000 _diffrn_orient_matrix_UB_32 -0.1238282000 _diffrn_orient_matrix_UB_33 -0.0254938000 _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 0.0435 _diffrn_reflns_av_unetI/netI 0.0247 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 23232 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.977 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.812 _diffrn_reflns_theta_min 4.865 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.300 _exptl_absorpt_correction_T_max 0.770 _exptl_absorpt_correction_T_min 0.633 _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 1.347 _exptl_crystal_description block _exptl_crystal_F_000 1008 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.164 _exptl_crystal_size_min 0.102 _refine_diff_density_max 0.512 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.057 _refine_ls_abs_structure_details ; Flack x determined using 2186 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.002(17) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 277 _refine_ls_number_reflns 4871 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.042 _refine_ls_R_factor_all 0.0405 _refine_ls_R_factor_gt 0.0400 _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^)+(0.0623P)^2^+1.7235P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1074 _refine_ls_wR_factor_ref 0.1081 _reflns_Friedel_coverage 0.894 _reflns_Friedel_fraction_full 0.992 _reflns_Friedel_fraction_max 0.956 _reflns_number_gt 4812 _reflns_number_total 4871 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc02577c2.cif _cod_data_source_block jjw0957 _cod_database_code 1577315 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C72 H124 Cl4 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 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _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. Others Sof(Cl1B)=Sof(P1B)=1-FVAR(1) Sof(Cl1)=Sof(P1)=FVAR(1) 3.a Ternary CH refined with riding coordinates: C6(H6), C9(H9), C12(H12) 3.b Secondary CH2 refined with riding coordinates: C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B) 3.c Idealised Me refined as rotating group: C4(H4A,H4B,H4C), C5(H5A,H5B,H5C), C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C10(H10A, H10B,H10C), C11(H11A,H11B,H11C) ; _shelx_res_file ; TITL jjw0957_a.res in Pna2(1) jjw0957.res created by SHELXL-2018/3 at 20:15:07 on 11-Jan-2026 REM Old TITL jjw0957 in Pna21 #33 REM SHELXT solution in Pna2(1) REM R1 0.073, Rweak 0.025, Alpha 0.002, Orientation as input REM Flack x = 0.079 ( 0.014 ) from Parsons' quotients REM Formula found by SHELXT: C18 N2 O3 F3 P Cl2 CELL 1.54184 12.930122 10.766795 16.959492 90 90 90 ZERR 4 0.000145 0.000124 0.000213 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 Cl F N O P S UNIT 72 124 4 12 8 12 4 4 L.S. 10 PLAN 7 TEMP 100 CONF BOND $H LIST 6 MORE -1 fmap 2 acta REM REM REM WGHT 0.062300 1.723500 FVAR 0.36923 0.94253 PART 1 CL1 3 0.600560 0.457061 0.367329 21.00000 0.02303 0.02939 = 0.02512 0.00107 0.00137 0.00179 PART 2 CL1B 3 0.590426 0.547506 0.378308 -21.00000 0.04987 PART 1 P1 7 0.505800 0.558588 0.442327 21.00000 0.02045 0.02112 = 0.02140 0.00170 -0.00212 -0.00159 PART 2 P1B 7 0.489338 0.460074 0.456525 -21.00000 0.05819 PART 0 N1 5 0.319718 0.627061 0.373192 11.00000 0.02182 0.02405 = 0.02118 0.00043 -0.00042 0.00189 N2 5 0.332284 0.425328 0.370368 11.00000 0.02518 0.02466 = 0.02326 0.00172 -0.00237 0.00037 C1 1 0.379684 0.530348 0.395155 11.00000 0.02058 0.02533 = 0.02065 -0.00029 -0.00062 0.00178 C2 1 0.233190 0.583493 0.334964 11.00000 0.02184 0.02809 = 0.02078 0.00211 -0.00051 -0.00139 C3 1 0.241438 0.456908 0.332514 11.00000 0.02478 0.02890 = 0.02452 0.00088 -0.00029 -0.00103 C4 1 0.146925 0.662189 0.304898 11.00000 0.02457 0.03194 = 0.03143 0.00516 -0.00541 0.00100 AFIX 137 H4A 2 0.128933 0.723035 0.343935 11.00000 -1.50000 H4B 2 0.087931 0.610859 0.293978 11.00000 -1.50000 H4C 2 0.168357 0.703353 0.257419 11.00000 -1.50000 AFIX 0 C5 1 0.166485 0.367412 0.297378 11.00000 0.03483 0.03035 = 0.03831 0.00019 -0.01005 -0.00478 AFIX 137 H5A 2 0.194869 0.333607 0.249678 11.00000 -1.50000 H5B 2 0.102887 0.409597 0.285723 11.00000 -1.50000 H5C 2 0.153438 0.301405 0.334110 11.00000 -1.50000 AFIX 0 C6 1 0.344274 0.759684 0.392973 11.00000 0.02663 0.02373 = 0.03094 -0.00336 -0.00204 -0.00153 AFIX 13 H6 2 0.416790 0.761445 0.409742 11.00000 -1.20000 AFIX 0 C7 1 0.335968 0.845484 0.321639 11.00000 0.03550 0.02496 = 0.03589 0.00161 0.00242 -0.00379 AFIX 137 H7A 2 0.370077 0.807987 0.277353 11.00000 -1.50000 H7B 2 0.368193 0.923598 0.333526 11.00000 -1.50000 H7C 2 0.264410 0.858846 0.309160 11.00000 -1.50000 AFIX 0 C8 1 0.280260 0.800522 0.463749 11.00000 0.03606 0.02901 = 0.03010 -0.00500 0.00074 0.00033 AFIX 137 H8A 2 0.295259 0.885777 0.475747 11.00000 -1.50000 H8B 2 0.297107 0.749575 0.508393 11.00000 -1.50000 H8C 2 0.208061 0.791956 0.451722 11.00000 -1.50000 AFIX 0 C9 1 0.371904 0.297967 0.387832 11.00000 0.02635 0.02238 = 0.03478 0.00143 -0.00337 0.00150 PART 1 AFIX 13 H9 2 0.442269 0.307786 0.408379 11.00000 -1.20000 AFIX 0 PART 0 C10 1 0.379872 0.217063 0.314157 11.00000 0.04055 0.02468 = 0.04274 -0.00791 -0.00358 0.00135 AFIX 137 H10A 2 0.312053 0.189975 0.298828 11.00000 -1.50000 H10B 2 0.422340 0.146030 0.325211 11.00000 -1.50000 H10C 2 0.410233 0.264310 0.272101 11.00000 -1.50000 AFIX 0 C11 1 0.308119 0.239303 0.453111 11.00000 0.02880 0.02842 = 0.04052 0.01009 -0.00525 -0.00355 AFIX 137 H11A 2 0.309737 0.291715 0.498888 11.00000 -1.50000 H11B 2 0.336338 0.159398 0.466072 11.00000 -1.50000 H11C 2 0.237947 0.229701 0.435652 11.00000 -1.50000 AFIX 0 PART 1 C12 1 0.503479 0.460094 0.530369 11.00000 0.02660 0.02766 = 0.02102 0.00124 -0.00261 -0.00090 AFIX 13 H12 2 0.488391 0.374160 0.515189 11.00000 -1.20000 AFIX 0 PART 0 C13 1 0.418659 0.507862 0.586388 11.00000 0.02698 0.03884 = 0.02679 0.00334 -0.00097 0.00064 AFIX 23 H13A 2 0.432004 0.593840 0.600115 11.00000 -1.20000 H13B 2 0.351798 0.503399 0.560605 11.00000 -1.20000 AFIX 0 C14 1 0.418089 0.428127 0.660622 11.00000 0.03587 0.05015 = 0.02516 0.00608 0.00102 0.00001 AFIX 23 H14A 2 0.399379 0.343605 0.646891 11.00000 -1.20000 H14B 2 0.366440 0.459619 0.696967 11.00000 -1.20000 AFIX 0 C15 1 0.523759 0.428273 0.700889 11.00000 0.04037 0.04435 = 0.02355 0.00192 -0.00497 0.00066 AFIX 23 H15A 2 0.538746 0.511240 0.720031 11.00000 -1.20000 H15B 2 0.521876 0.372869 0.745967 11.00000 -1.20000 AFIX 0 C16 1 0.609610 0.387232 0.645099 11.00000 0.03974 0.03738 = 0.02664 0.00012 -0.00794 0.00786 AFIX 23 H16A 2 0.599602 0.300695 0.631142 11.00000 -1.20000 H16B 2 0.675869 0.394656 0.671503 11.00000 -1.20000 AFIX 0 C17 1 0.610247 0.466428 0.570090 11.00000 0.02624 0.03437 = 0.02785 0.00034 -0.00205 0.00179 AFIX 23 H17A 2 0.662778 0.436000 0.534117 11.00000 -1.20000 H17B 2 0.626564 0.551884 0.583251 11.00000 -1.20000 AFIX 0 S1 8 0.566983 1.027156 0.502723 11.00000 0.02718 0.02943 = 0.02743 -0.00352 -0.00082 -0.00134 F1 4 0.406107 1.021571 0.598255 11.00000 0.04135 0.08602 = 0.04541 -0.00060 0.01264 -0.00046 F2 4 0.552813 1.031312 0.657434 11.00000 0.06817 0.09341 = 0.02858 -0.01084 -0.00370 -0.01258 F3 4 0.503450 0.861065 0.605125 11.00000 0.09095 0.05067 = 0.06022 0.02070 0.00620 -0.01339 O1 6 0.556795 1.160035 0.501236 11.00000 0.04059 0.03162 = 0.05330 0.00086 0.00031 0.00141 O2 6 0.670705 0.982637 0.512057 11.00000 0.03253 0.04849 = 0.04264 0.00126 -0.00110 0.00859 O3 6 0.505016 0.964699 0.444648 11.00000 0.04301 0.04882 = 0.03216 -0.00667 -0.00241 -0.01287 C18 1 0.504841 0.983623 0.595773 11.00000 0.04596 0.05044 = 0.03043 0.00137 -0.00139 -0.00742 HKLF 4 REM jjw0957_a.res in Pna2(1) REM wR2 = 0.1081, GooF = S = 1.043, Restrained GooF = 1.042 for all data REM R1 = 0.0400 for 4812 Fo > 4sig(Fo) and 0.0405 for all 4871 data REM 277 parameters refined using 1 restraints END WGHT 0.0623 1.7235 REM Highest difference peak 0.512, deepest hole -0.234, 1-sigma level 0.057 Q1 1 0.5635 0.9365 0.5059 11.00000 0.05 0.51 Q2 1 0.4937 0.4085 0.4257 11.00000 0.05 0.39 Q3 1 0.5588 0.8443 0.5048 11.00000 0.05 0.37 Q4 1 0.4967 0.5727 0.5519 11.00000 0.05 0.29 Q5 1 0.5989 0.5319 0.3499 11.00000 0.05 0.28 Q6 1 0.6036 0.3504 0.3792 11.00000 0.05 0.27 Q7 1 0.6041 0.5540 0.4099 11.00000 0.05 0.26 ; _shelx_res_checksum 85136 _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 1.408 _oxdiff_exptl_absorpt_empirical_full_min 0.781 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 Cl1 Cl 0.60056(7) 0.45706(9) 0.36733(5) 0.0258(2) Uani 0.943(4) 1 d . . P A 1 Cl1B Cl 0.5904(18) 0.548(2) 0.3783(15) 0.050(6) Uiso 0.057(4) 1 d . . P A 2 P1 P 0.50580(7) 0.55859(9) 0.44233(6) 0.0210(2) Uani 0.943(4) 1 d . . P A 1 P1B P 0.489(2) 0.460(3) 0.4565(19) 0.058(8) Uiso 0.057(4) 1 d . . P A 2 N1 N 0.3197(2) 0.6271(3) 0.37319(18) 0.0224(6) Uani 1 1 d . . . . . N2 N 0.3323(2) 0.4253(3) 0.37037(19) 0.0244(6) Uani 1 1 d . . . . . C1 C 0.3797(3) 0.5303(3) 0.3952(2) 0.0222(7) Uani 1 1 d . . . . . C2 C 0.2332(3) 0.5835(4) 0.3350(2) 0.0236(7) Uani 1 1 d . . . . . C3 C 0.2414(3) 0.4569(4) 0.3325(2) 0.0261(7) Uani 1 1 d . . . . . C4 C 0.1469(3) 0.6622(4) 0.3049(2) 0.0293(8) Uani 1 1 d . . . . . H4A H 0.128933 0.723035 0.343935 0.044 Uiso 1 1 calc R U . . . H4B H 0.087931 0.610859 0.293978 0.044 Uiso 1 1 calc R U . . . H4C H 0.168357 0.703353 0.257419 0.044 Uiso 1 1 calc R U . . . C5 C 0.1665(3) 0.3674(4) 0.2974(3) 0.0345(9) Uani 1 1 d . . . . . H5A H 0.194869 0.333607 0.249678 0.052 Uiso 1 1 calc R U . . . H5B H 0.102887 0.409597 0.285723 0.052 Uiso 1 1 calc R U . . . H5C H 0.153438 0.301405 0.334110 0.052 Uiso 1 1 calc R U . . . C6 C 0.3443(3) 0.7597(3) 0.3930(2) 0.0271(8) Uani 1 1 d . . . . . H6 H 0.416790 0.761445 0.409742 0.033 Uiso 1 1 calc R U . . . C7 C 0.3360(3) 0.8455(4) 0.3216(2) 0.0321(8) Uani 1 1 d . . . . . H7A H 0.370077 0.807987 0.277353 0.048 Uiso 1 1 calc R U . . . H7B H 0.368193 0.923598 0.333526 0.048 Uiso 1 1 calc R U . . . H7C H 0.264410 0.858846 0.309160 0.048 Uiso 1 1 calc R U . . . C8 C 0.2803(3) 0.8005(4) 0.4637(2) 0.0317(8) Uani 1 1 d . . . . . H8A H 0.295259 0.885777 0.475747 0.048 Uiso 1 1 calc R U . . . H8B H 0.297107 0.749575 0.508393 0.048 Uiso 1 1 calc R U . . . H8C H 0.208061 0.791956 0.451722 0.048 Uiso 1 1 calc R U . . . C9 C 0.3719(3) 0.2980(3) 0.3878(2) 0.0278(7) Uani 1 1 d . . . . . H9 H 0.442269 0.307786 0.408379 0.033 Uiso 1 1 calc R U . B 1 C10 C 0.3799(4) 0.2171(4) 0.3142(3) 0.0360(9) Uani 1 1 d . . . . . H10A H 0.312053 0.189975 0.298828 0.054 Uiso 1 1 calc R U . . . H10B H 0.422340 0.146030 0.325211 0.054 Uiso 1 1 calc R U . . . H10C H 0.410233 0.264310 0.272101 0.054 Uiso 1 1 calc R U . . . C11 C 0.3081(3) 0.2393(4) 0.4531(3) 0.0326(8) Uani 1 1 d . . . . . H11A H 0.309737 0.291715 0.498888 0.049 Uiso 1 1 calc R U . . . H11B H 0.336338 0.159398 0.466072 0.049 Uiso 1 1 calc R U . . . H11C H 0.237947 0.229701 0.435652 0.049 Uiso 1 1 calc R U . . . C12 C 0.5035(3) 0.4601(4) 0.5304(2) 0.0251(8) Uani 1 1 d . . . A 1 H12 H 0.488391 0.374160 0.515189 0.030 Uiso 1 1 calc R U . A 1 C13 C 0.4187(3) 0.5079(4) 0.5864(2) 0.0309(8) Uani 1 1 d . . . . . H13A H 0.432004 0.593840 0.600115 0.037 Uiso 1 1 calc R U . A 1 H13B H 0.351798 0.503399 0.560605 0.037 Uiso 1 1 calc R U . A 1 C14 C 0.4181(4) 0.4281(5) 0.6606(3) 0.0371(9) Uani 1 1 d . . . . . H14A H 0.399379 0.343605 0.646891 0.044 Uiso 1 1 calc R U . . . H14B H 0.366440 0.459619 0.696967 0.044 Uiso 1 1 calc R U . . . C15 C 0.5238(4) 0.4283(5) 0.7009(2) 0.0361(9) Uani 1 1 d . . . . . H15A H 0.538746 0.511240 0.720031 0.043 Uiso 1 1 calc R U . . . H15B H 0.521876 0.372869 0.745967 0.043 Uiso 1 1 calc R U . . . C16 C 0.6096(3) 0.3872(4) 0.6451(2) 0.0346(9) Uani 1 1 d . . . . . H16A H 0.599602 0.300695 0.631142 0.042 Uiso 1 1 calc R U . . . H16B H 0.675869 0.394656 0.671503 0.042 Uiso 1 1 calc R U . . . C17 C 0.6102(3) 0.4664(4) 0.5701(2) 0.0295(8) Uani 1 1 d . . . . . H17A H 0.662778 0.436000 0.534117 0.035 Uiso 1 1 calc R U . A 1 H17B H 0.626564 0.551884 0.583251 0.035 Uiso 1 1 calc R U . A 1 S1 S 0.56698(7) 1.02716(8) 0.50272(6) 0.0280(2) Uani 1 1 d . . . . . F1 F 0.4061(2) 1.0216(4) 0.59825(19) 0.0576(9) Uani 1 1 d . . . . . F2 F 0.5528(3) 1.0313(4) 0.65743(19) 0.0634(10) Uani 1 1 d . . . . . F3 F 0.5034(3) 0.8611(3) 0.6051(2) 0.0673(10) Uani 1 1 d . . . . . O1 O 0.5568(2) 1.1600(3) 0.5012(2) 0.0418(7) Uani 1 1 d . . . . . O2 O 0.6707(2) 0.9826(3) 0.5121(2) 0.0412(7) Uani 1 1 d . . . . . O3 O 0.5050(3) 0.9647(3) 0.4446(2) 0.0413(7) Uani 1 1 d . . . . . C18 C 0.5048(4) 0.9836(5) 0.5958(3) 0.0423(11) 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 Cl1 0.0230(4) 0.0294(5) 0.0251(4) 0.0011(4) 0.0014(3) 0.0018(3) P1 0.0205(4) 0.0211(4) 0.0214(4) 0.0017(4) -0.0021(3) -0.0016(3) N1 0.0218(13) 0.0240(14) 0.0212(13) 0.0004(12) -0.0004(11) 0.0019(11) N2 0.0252(14) 0.0247(14) 0.0233(14) 0.0017(13) -0.0024(13) 0.0004(11) C1 0.0206(16) 0.0253(17) 0.0207(15) -0.0003(13) -0.0006(12) 0.0018(13) C2 0.0218(16) 0.0281(18) 0.0208(15) 0.0021(14) -0.0005(13) -0.0014(14) C3 0.0248(18) 0.0289(19) 0.0245(17) 0.0009(14) -0.0003(14) -0.0010(14) C4 0.0246(17) 0.0319(19) 0.0314(18) 0.0052(16) -0.0054(14) 0.0010(15) C5 0.035(2) 0.030(2) 0.038(2) 0.0002(17) -0.0100(17) -0.0048(17) C6 0.0266(17) 0.0237(17) 0.0309(18) -0.0034(14) -0.0020(15) -0.0015(14) C7 0.0355(19) 0.0250(18) 0.036(2) 0.0016(16) 0.0024(16) -0.0038(15) C8 0.0361(19) 0.0290(18) 0.0301(19) -0.0050(15) 0.0007(16) 0.0003(15) C9 0.0263(16) 0.0224(17) 0.0348(19) 0.0014(15) -0.0034(14) 0.0015(14) C10 0.041(2) 0.0247(19) 0.043(2) -0.0079(17) -0.0036(18) 0.0013(16) C11 0.0288(18) 0.0284(18) 0.041(2) 0.0101(17) -0.0052(16) -0.0036(14) C12 0.0266(18) 0.0277(18) 0.0210(17) 0.0012(13) -0.0026(14) -0.0009(14) C13 0.0270(18) 0.039(2) 0.0268(19) 0.0033(17) -0.0010(15) 0.0006(16) C14 0.036(2) 0.050(3) 0.0252(19) 0.0061(18) 0.0010(16) 0.0000(18) C15 0.040(2) 0.044(2) 0.0235(19) 0.0019(17) -0.0050(17) 0.0007(19) C16 0.040(2) 0.037(2) 0.0266(19) 0.0001(16) -0.0079(16) 0.0079(17) C17 0.0262(18) 0.034(2) 0.028(2) 0.0003(15) -0.0020(15) 0.0018(15) S1 0.0272(4) 0.0294(4) 0.0274(4) -0.0035(4) -0.0008(4) -0.0013(3) F1 0.0413(16) 0.086(3) 0.0454(17) -0.0006(15) 0.0126(13) -0.0005(15) F2 0.068(2) 0.093(3) 0.0286(14) -0.0108(16) -0.0037(13) -0.0126(19) F3 0.091(3) 0.0507(19) 0.060(2) 0.0207(16) 0.0062(18) -0.0134(18) O1 0.0406(16) 0.0316(15) 0.0533(17) 0.0009(16) 0.0003(15) 0.0014(12) O2 0.0325(16) 0.0485(18) 0.0426(18) 0.0013(15) -0.0011(13) 0.0086(13) O3 0.0430(17) 0.0488(19) 0.0322(15) -0.0067(16) -0.0024(13) -0.0129(13) C18 0.046(3) 0.050(3) 0.030(2) 0.001(2) -0.0014(19) -0.007(2) 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' Cl Cl 0.3639 0.7018 '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 -1 -6 5 0.0407 2 6 -4 0.0526 5 0 9 0.0532 -7 1 5 0.0758 -8 2 -2 0.0781 2 0 -11 0.0770 7 -2 -5 0.0757 -4 -5 -7 0.0889 0 4 -9 0.0791 -7 -4 0 0.0695 -4 4 -8 0.0793 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 Cl1 99.76(12) . . ? C12 P1 Cl1 101.78(13) . . ? C12 P1 C1 104.12(17) . . ? C1 P1B Cl1B 86.6(14) . . ? C1 N1 C2 109.5(3) . . ? C1 N1 C6 123.4(3) . . ? C2 N1 C6 127.0(3) . . ? C1 N2 C3 108.9(3) . . ? C1 N2 C9 123.4(3) . . ? C3 N2 C9 127.6(3) . . ? N1 C1 P1 120.1(3) . . ? N1 C1 P1B 151.6(9) . . ? N1 C1 N2 107.4(3) . . ? N2 C1 P1 132.4(3) . . ? N2 C1 P1B 100.0(9) . . ? N1 C2 C4 125.2(3) . . ? C3 C2 N1 106.9(3) . . ? C3 C2 C4 127.9(3) . . ? N2 C3 C5 125.4(3) . . ? C2 C3 N2 107.3(3) . . ? C2 C3 C5 127.3(4) . . ? C2 C4 H4A 109.5 . . ? C2 C4 H4B 109.5 . . ? C2 C4 H4C 109.5 . . ? H4A C4 H4B 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5B 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 H6 106.6 . . ? N1 C6 C7 112.6(3) . . ? N1 C6 C8 109.6(3) . . ? C7 C6 H6 106.6 . . ? C8 C6 H6 106.6 . . ? C8 C6 C7 114.3(3) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7B 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 H9 106.9 . . ? N2 C9 C10 112.6(3) . . ? N2 C9 C11 109.9(3) . . ? C10 C9 H9 106.9 . . ? C11 C9 H9 106.9 . . ? C11 C9 C10 113.3(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10B 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? P1 C12 H12 109.6 . . ? C13 C12 P1 108.7(3) . . ? C13 C12 H12 109.6 . . ? C17 C12 P1 108.5(3) . . ? C17 C12 H12 109.6 . . ? C17 C12 C13 110.8(3) . . ? C12 C13 H13A 109.9 . . ? C12 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? C14 C13 C12 109.0(3) . . ? C14 C13 H13A 109.9 . . ? C14 C13 H13B 109.9 . . ? C13 C14 H14A 109.4 . . ? C13 C14 H14B 109.4 . . ? C13 C14 C15 111.4(4) . . ? H14A C14 H14B 108.0 . . ? C15 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C14 C15 H15A 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C16 C15 C14 111.9(4) . . ? C16 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C15 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C15 C16 C17 111.0(3) . . ? H16A C16 H16B 108.0 . . ? C17 C16 H16A 109.4 . . ? C17 C16 H16B 109.4 . . ? C12 C17 H17A 109.8 . . ? C12 C17 H17B 109.8 . . ? C16 C17 C12 109.5(3) . . ? C16 C17 H17A 109.8 . . ? C16 C17 H17B 109.8 . . ? H17A C17 H17B 108.2 . . ? O1 S1 C18 103.3(2) . . ? O2 S1 O1 114.9(2) . . ? O2 S1 O3 116.2(2) . . ? O2 S1 C18 103.3(2) . . ? O3 S1 O1 113.8(2) . . ? O3 S1 C18 103.1(2) . . ? F1 C18 S1 111.5(3) . . ? F2 C18 S1 112.1(4) . . ? F2 C18 F1 107.7(4) . . ? F2 C18 F3 107.3(4) . . ? F3 C18 S1 111.3(4) . . ? F3 C18 F1 106.6(4) . . ? 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 Cl1 P1 2.0770(14) . ? Cl1B P1B 2.09(4) . ? P1 C1 1.842(4) . ? P1 C12 1.832(4) . ? P1B C1 1.91(3) . ? N1 C1 1.351(5) . ? N1 C2 1.376(5) . ? N1 C6 1.501(5) . ? N2 C1 1.353(5) . ? N2 C3 1.381(5) . ? N2 C9 1.493(5) . ? C2 C3 1.368(5) . ? C2 C4 1.491(5) . ? C3 C5 1.491(5) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6 0.9800 . ? C6 C7 1.526(5) . ? C6 C8 1.523(5) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 H9 0.9800 . ? C9 C10 1.527(6) . ? C9 C11 1.518(5) . ? 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 H12 0.9800 . ? C12 C13 1.539(5) . ? C12 C17 1.538(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C13 C14 1.524(6) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C14 C15 1.527(6) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C15 C16 1.524(6) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16 C17 1.531(6) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? S1 O1 1.437(3) . ? S1 O2 1.433(3) . ? S1 O3 1.437(3) . ? S1 C18 1.832(5) . ? F1 C18 1.341(6) . ? F2 C18 1.320(6) . ? F3 C18 1.329(6) . ? 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 Cl1 P1 C1 N1 -125.1(3) . . . . ? Cl1 P1 C1 N2 49.1(4) . . . . ? Cl1 P1 C12 C13 -168.5(2) . . . . ? Cl1 P1 C12 C17 71.0(3) . . . . ? P1 C12 C13 C14 -178.7(3) . . . . ? P1 C12 C17 C16 178.6(3) . . . . ? N1 C2 C3 N2 0.9(4) . . . . ? N1 C2 C3 C5 179.7(4) . . . . ? C1 P1 C12 C13 -65.1(3) . . . . ? C1 P1 C12 C17 174.3(3) . . . . ? C1 N1 C2 C3 -0.9(4) . . . . ? C1 N1 C2 C4 177.4(3) . . . . ? C1 N1 C6 C7 131.9(4) . . . . ? C1 N1 C6 C8 -99.7(4) . . . . ? C1 N2 C3 C2 -0.5(4) . . . . ? C1 N2 C3 C5 -179.4(4) . . . . ? C1 N2 C9 C10 -129.4(4) . . . . ? C1 N2 C9 C11 103.2(4) . . . . ? C2 N1 C1 P1 176.1(3) . . . . ? C2 N1 C1 P1B -164(2) . . . . ? C2 N1 C1 N2 0.6(4) . . . . ? C2 N1 C6 C7 -51.8(5) . . . . ? C2 N1 C6 C8 76.6(4) . . . . ? C3 N2 C1 P1 -174.8(3) . . . . ? C3 N2 C1 P1B 172.4(10) . . . . ? C3 N2 C1 N1 -0.1(4) . . . . ? C3 N2 C9 C10 55.2(5) . . . . ? C3 N2 C9 C11 -72.2(5) . . . . ? C4 C2 C3 N2 -177.4(4) . . . . ? C4 C2 C3 C5 1.4(7) . . . . ? C6 N1 C1 P1 -7.0(5) . . . . ? C6 N1 C1 P1B 13(2) . . . . ? C6 N1 C1 N2 177.5(3) . . . . ? C6 N1 C2 C3 -177.6(3) . . . . ? C6 N1 C2 C4 0.7(6) . . . . ? C9 N2 C1 P1 9.0(6) . . . . ? C9 N2 C1 P1B -3.8(10) . . . . ? C9 N2 C1 N1 -176.2(3) . . . . ? C9 N2 C3 C2 175.5(3) . . . . ? C9 N2 C3 C5 -3.4(6) . . . . ? C12 P1 C1 N1 130.0(3) . . . . ? C12 P1 C1 N2 -55.8(4) . . . . ? C12 C13 C14 C15 57.0(5) . . . . ? C13 C12 C17 C16 59.4(4) . . . . ? C13 C14 C15 C16 -55.5(5) . . . . ? C14 C15 C16 C17 54.8(5) . . . . ? C15 C16 C17 C12 -56.2(5) . . . . ? C17 C12 C13 C14 -59.6(4) . . . . ? O1 S1 C18 F1 58.4(4) . . . . ? O1 S1 C18 F2 -62.5(4) . . . . ? O1 S1 C18 F3 177.3(3) . . . . ? O2 S1 C18 F1 178.4(4) . . . . ? O2 S1 C18 F2 57.5(4) . . . . ? O2 S1 C18 F3 -62.7(4) . . . . ? O3 S1 C18 F1 -60.3(4) . . . . ? O3 S1 C18 F2 178.9(4) . . . . ? O3 S1 C18 F3 58.6(4) . . . . ? 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 -1.0000 -6.0000 5.0000 -0.6411 0.3229 0.6649 2.0000 6.0000 -4.0000 0.5781 -0.2094 -0.7397 5.0000 0.0000 9.0000 -0.6625 0.5981 -0.4763 -7.0000 1.0000 5.0000 -0.5700 -0.7668 0.0943 -8.0000 2.0000 -2.0000 0.0445 -0.9915 0.1983 2.0000 -0.0000 -11.0000 1.0026 0.1268 0.1817 7.0000 -2.0000 -5.0000 0.5395 0.8318 0.0295 -4.0000 -5.0000 -7.0000 0.3600 -0.1519 0.9951 -0.0000 4.0000 -9.0000 0.9036 -0.3294 -0.2659 -7.0000 -4.0000 -0.0000 -0.2886 -0.4803 0.8409 -4.0000 4.0000 -8.0000 0.7216 -0.7447 -0.0939