# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2023 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_sh5173_a _database_code_depnum_ccdc_archive 'CCDC 2260785' loop_ _audit_author_name _audit_author_address 'Bernd Morgenstern' ;Universitaet des Saarlandes Germany ; _audit_update_record ; 2023-05-05 deposited with the CCDC. 2023-09-08 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 O4 P, F6 P' _chemical_formula_sum 'C16 H36 F6 O4 P2' _chemical_formula_weight 468.39 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' F F 0.0171 0.0103 '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _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. ; 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' _cell_length_a 9.6155(2) _cell_length_b 15.4439(4) _cell_length_c 15.4444(4) _cell_angle_alpha 90 _cell_angle_beta 93.6150(10) _cell_angle_gamma 90 _cell_volume 2288.94(10) _cell_formula_units_Z 4 _cell_measurement_temperature 154(2) _cell_measurement_reflns_used 4282 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 25.55 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.359 _exptl_crystal_F_000 992 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.020 _exptl_absorpt_coefficient_mu 0.256 _shelx_estimated_absorpt_T_min 0.951 _shelx_estimated_absorpt_T_max 0.995 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7070 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 154(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'sealed tube' _diffrn_measurement_device_type 'Bruker X8 Apex, Nonius Kappa CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22277 _diffrn_reflns_av_unetI/netI 0.0433 _diffrn_reflns_av_R_equivalents 0.0407 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.867 _diffrn_reflns_theta_max 27.918 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 5485 _reflns_number_gt 4021 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX3 (Bruker, 2010)' _computing_cell_refinement 'SAINT (Bruker, 2010)' _computing_data_reduction 'SAINT (Bruker, 2010)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _computing_structure_refinement ; SHELXL-2018/3 (Sheldrick, 2018), SHELXLe Rev 1000 (Huebschle et al., 2011) ; _computing_molecular_graphics 'DIAMOND, Vers. 4.5.3 (Brandenburg, K. 2018)' _computing_publication_material 'CIFTAB-2014 (Sheldrick, G. M.)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+0.7646P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5485 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0630 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0794 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.25683(4) 0.40747(3) 0.15230(3) 0.01967(11) Uani 1 1 d . . . . . O1 O 0.01016(13) 0.19123(8) 0.01432(9) 0.0319(3) Uani 1 1 d . . . . . O2 O 0.09164(12) 0.47373(8) -0.11544(8) 0.0275(3) Uani 1 1 d . . . . . O3 O 0.08235(13) 0.59743(9) 0.34392(8) 0.0340(3) Uani 1 1 d . . . . . O4 O 0.64765(12) 0.42500(8) 0.30599(9) 0.0343(3) Uani 1 1 d . . . . . C1 C 0.17141(17) 0.30701(11) 0.12462(12) 0.0238(4) Uani 1 1 d . . . . . H1A H 0.215457 0.281081 0.074502 0.029 Uiso 1 1 calc R U . . . H1B H 0.185371 0.266541 0.174118 0.029 Uiso 1 1 calc R U . . . C2 C 0.01492(17) 0.31697(11) 0.10188(13) 0.0270(4) Uani 1 1 d . . . . . H2A H -0.028937 0.345453 0.150701 0.032 Uiso 1 1 calc R U . . . H2B H 0.000493 0.354637 0.050228 0.032 Uiso 1 1 calc R U . . . C3 C -0.05450(18) 0.23096(12) 0.08362(13) 0.0295(4) Uani 1 1 d . . . . . H3A H -0.044937 0.193733 0.135841 0.035 Uiso 1 1 calc R U . . . H3B H -0.154986 0.239507 0.067965 0.035 Uiso 1 1 calc R U . . . C4 C -0.0543(2) 0.11191(13) -0.00933(16) 0.0453(6) Uani 1 1 d . . . . . H4A H -0.150666 0.122624 -0.031228 0.068 Uiso 1 1 calc R U . . . H4B H -0.053924 0.073900 0.041488 0.068 Uiso 1 1 calc R U . . . H4C H -0.003177 0.084118 -0.054695 0.068 Uiso 1 1 calc R U . . . C5 C 0.22720(17) 0.48249(11) 0.06475(11) 0.0219(4) Uani 1 1 d . . . . . H5A H 0.125665 0.487602 0.050651 0.026 Uiso 1 1 calc R U . . . H5B H 0.262228 0.540199 0.083609 0.026 Uiso 1 1 calc R U . . . C6 C 0.29816(16) 0.45566(12) -0.01688(12) 0.0266(4) Uani 1 1 d . . . . . H6A H 0.398033 0.471476 -0.010206 0.032 Uiso 1 1 calc R U . . . H6B H 0.292041 0.391989 -0.023497 0.032 Uiso 1 1 calc R U . . . C7 C 0.23309(17) 0.49814(13) -0.09757(12) 0.0278(4) Uani 1 1 d . . . . . H7A H 0.238345 0.561798 -0.090592 0.033 Uiso 1 1 calc R U . . . H7B H 0.287213 0.482223 -0.147643 0.033 Uiso 1 1 calc R U . . . C8 C 0.0770(2) 0.38747(12) -0.14681(14) 0.0366(5) Uani 1 1 d . . . . . H8A H -0.021592 0.375463 -0.162128 0.055 Uiso 1 1 calc R U . . . H8B H 0.111846 0.346981 -0.101652 0.055 Uiso 1 1 calc R U . . . H8C H 0.130561 0.380511 -0.198269 0.055 Uiso 1 1 calc R U . . . C9 C 0.18817(17) 0.45012(11) 0.24882(11) 0.0220(4) Uani 1 1 d . . . . . H9A H 0.093131 0.472491 0.234095 0.026 Uiso 1 1 calc R U . . . H9B H 0.180179 0.402320 0.290931 0.026 Uiso 1 1 calc R U . . . C10 C 0.27580(17) 0.52264(11) 0.29239(11) 0.0249(4) Uani 1 1 d . . . . . H10A H 0.369926 0.500254 0.309779 0.030 Uiso 1 1 calc R U . . . H10B H 0.286179 0.570333 0.250454 0.030 Uiso 1 1 calc R U . . . C11 C 0.20906(19) 0.55698(12) 0.37123(12) 0.0276(4) Uani 1 1 d . . . . . H11A H 0.191485 0.508905 0.411505 0.033 Uiso 1 1 calc R U . . . H11B H 0.271895 0.599187 0.402036 0.033 Uiso 1 1 calc R U . . . C12 C 0.0116(2) 0.62946(14) 0.41515(14) 0.0425(5) Uani 1 1 d . . . . . H12A H -0.075079 0.657746 0.393760 0.064 Uiso 1 1 calc R U . . . H12B H 0.071063 0.671431 0.447497 0.064 Uiso 1 1 calc R U . . . H12C H -0.009969 0.581322 0.453411 0.064 Uiso 1 1 calc R U . . . C13 C 0.44040(16) 0.38876(11) 0.17093(12) 0.0248(4) Uani 1 1 d . . . . . H13A H 0.476572 0.364623 0.117385 0.030 Uiso 1 1 calc R U . . . H13B H 0.487336 0.444981 0.182643 0.030 Uiso 1 1 calc R U . . . C14 C 0.47892(18) 0.32709(12) 0.24640(13) 0.0294(4) Uani 1 1 d . . . . . H14A H 0.418441 0.338803 0.294615 0.035 Uiso 1 1 calc R U . . . H14B H 0.462860 0.266558 0.227191 0.035 Uiso 1 1 calc R U . . . C15 C 0.62984(19) 0.33830(12) 0.27804(14) 0.0350(5) Uani 1 1 d . . . . . H15A H 0.653710 0.298065 0.326629 0.042 Uiso 1 1 calc R U . . . H15B H 0.691437 0.325722 0.230597 0.042 Uiso 1 1 calc R U . . . C16 C 0.7861(2) 0.44252(16) 0.33815(17) 0.0542(7) Uani 1 1 d . . . . . H16A H 0.850187 0.431074 0.292617 0.081 Uiso 1 1 calc R U . . . H16B H 0.810043 0.405245 0.388240 0.081 Uiso 1 1 calc R U . . . H16C H 0.793766 0.503361 0.355845 0.081 Uiso 1 1 calc R U . . . P2 P 0.93794(5) 0.78167(3) 0.61299(3) 0.02608(12) Uani 1 1 d . . . . . F1 F 0.88973(13) 0.81860(8) 0.51963(8) 0.0499(3) Uani 1 1 d . . . . . F2 F 0.89404(12) 0.68634(7) 0.58211(8) 0.0398(3) Uani 1 1 d . . . . . F3 F 1.09028(11) 0.76649(7) 0.58112(8) 0.0395(3) Uani 1 1 d . . . . . F4 F 0.98048(12) 0.87734(7) 0.64366(8) 0.0441(3) Uani 1 1 d . . . . . F5 F 0.78559(12) 0.79675(8) 0.64513(10) 0.0561(4) Uani 1 1 d . . . . . F6 F 0.98735(15) 0.74451(9) 0.70585(8) 0.0569(4) 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 0.0191(2) 0.0193(2) 0.0207(2) -0.00196(18) 0.00183(17) -0.00035(17) O1 0.0358(7) 0.0261(7) 0.0333(8) -0.0091(6) -0.0008(6) -0.0037(6) O2 0.0230(6) 0.0293(7) 0.0296(7) -0.0046(6) -0.0032(5) 0.0036(5) O3 0.0385(7) 0.0393(8) 0.0243(7) -0.0085(6) 0.0027(6) 0.0121(6) O4 0.0278(7) 0.0319(8) 0.0418(9) 0.0031(6) -0.0088(6) -0.0047(6) C1 0.0239(8) 0.0206(9) 0.0267(10) -0.0030(7) 0.0013(7) -0.0017(7) C2 0.0235(8) 0.0242(9) 0.0328(11) -0.0050(8) -0.0003(8) 0.0003(7) C3 0.0255(9) 0.0271(10) 0.0354(11) -0.0059(8) 0.0000(8) -0.0036(8) C4 0.0547(13) 0.0301(12) 0.0495(14) -0.0134(10) -0.0082(11) -0.0035(10) C5 0.0219(8) 0.0210(9) 0.0228(9) -0.0009(7) 0.0014(7) -0.0001(7) C6 0.0167(8) 0.0391(11) 0.0242(10) 0.0006(8) 0.0023(7) 0.0029(7) C7 0.0220(8) 0.0369(11) 0.0248(10) 0.0018(8) 0.0033(7) 0.0014(8) C8 0.0424(11) 0.0334(11) 0.0331(12) -0.0075(9) -0.0057(9) 0.0039(9) C9 0.0233(8) 0.0211(9) 0.0220(9) -0.0006(7) 0.0043(7) -0.0009(7) C10 0.0271(9) 0.0245(9) 0.0228(10) -0.0034(7) 0.0007(7) -0.0033(7) C11 0.0347(9) 0.0279(10) 0.0198(9) -0.0021(8) -0.0019(8) -0.0012(8) C12 0.0466(12) 0.0451(13) 0.0370(13) -0.0175(10) 0.0119(10) 0.0013(10) C13 0.0213(8) 0.0265(10) 0.0264(10) -0.0017(7) 0.0011(7) 0.0000(7) C14 0.0280(9) 0.0242(10) 0.0354(11) 0.0035(8) -0.0027(8) -0.0014(7) C15 0.0308(10) 0.0301(11) 0.0428(13) 0.0041(9) -0.0076(9) 0.0037(8) C16 0.0362(11) 0.0625(16) 0.0610(17) 0.0020(13) -0.0192(11) -0.0127(11) P2 0.0297(2) 0.0236(3) 0.0259(3) -0.00223(19) 0.0096(2) -0.00329(19) F1 0.0588(8) 0.0514(8) 0.0386(8) 0.0126(6) -0.0052(6) 0.0011(6) F2 0.0484(7) 0.0286(6) 0.0441(7) -0.0087(5) 0.0158(6) -0.0119(5) F3 0.0317(6) 0.0324(6) 0.0560(8) -0.0039(6) 0.0148(6) -0.0005(5) F4 0.0481(7) 0.0300(6) 0.0562(8) -0.0159(6) 0.0196(6) -0.0099(5) F5 0.0392(7) 0.0490(8) 0.0837(11) -0.0169(7) 0.0326(7) -0.0068(6) F6 0.0824(10) 0.0599(9) 0.0278(7) 0.0088(6) -0.0013(7) -0.0115(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C5 1.7898(17) . ? P1 C9 1.7933(17) . ? P1 C13 1.7939(16) . ? P1 C1 1.7945(17) . ? O1 C4 1.411(2) . ? O1 C3 1.412(2) . ? O2 C8 1.421(2) . ? O2 C7 1.422(2) . ? O3 C11 1.410(2) . ? O3 C12 1.418(2) . ? O4 C15 1.414(2) . ? O4 C16 1.417(2) . ? C1 C2 1.531(2) . ? C2 C3 1.505(2) . ? C5 C6 1.528(2) . ? C6 C7 1.509(2) . ? C9 C10 1.532(2) . ? C10 C11 1.508(2) . ? C13 C14 1.532(2) . ? C14 C15 1.512(2) . ? P2 F6 1.5894(13) . ? P2 F3 1.5918(11) . ? P2 F1 1.5920(13) . ? P2 F5 1.5932(12) . ? P2 F2 1.5963(11) . ? P2 F4 1.5970(12) . ? 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 C5 P1 C9 109.93(8) . . ? C5 P1 C13 109.49(8) . . ? C9 P1 C13 109.63(8) . . ? C5 P1 C1 109.33(8) . . ? C9 P1 C1 109.19(8) . . ? C13 P1 C1 109.26(8) . . ? C4 O1 C3 111.50(15) . . ? C8 O2 C7 112.82(14) . . ? C11 O3 C12 111.72(15) . . ? C15 O4 C16 112.38(15) . . ? C2 C1 P1 113.34(12) . . ? C3 C2 C1 111.84(14) . . ? O1 C3 C2 108.32(14) . . ? C6 C5 P1 112.94(12) . . ? C7 C6 C5 112.34(14) . . ? O2 C7 C6 112.76(14) . . ? C10 C9 P1 114.37(11) . . ? C11 C10 C9 111.20(14) . . ? O3 C11 C10 108.55(15) . . ? C14 C13 P1 114.23(12) . . ? C15 C14 C13 110.85(15) . . ? O4 C15 C14 107.60(15) . . ? F6 P2 F3 89.84(7) . . ? F6 P2 F1 179.48(8) . . ? F3 P2 F1 89.64(7) . . ? F6 P2 F5 90.00(8) . . ? F3 P2 F5 179.85(9) . . ? F1 P2 F5 90.51(8) . . ? F6 P2 F2 89.71(7) . . ? F3 P2 F2 90.17(6) . . ? F1 P2 F2 90.20(7) . . ? F5 P2 F2 89.82(6) . . ? F6 P2 F4 90.57(7) . . ? F3 P2 F4 90.26(6) . . ? F1 P2 F4 89.53(7) . . ? F5 P2 F4 89.76(6) . . ? F2 P2 F4 179.49(7) . . ? 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 C5 P1 C1 C2 -56.61(15) . . . . ? C9 P1 C1 C2 63.69(15) . . . . ? C13 P1 C1 C2 -176.42(13) . . . . ? P1 C1 C2 C3 -176.99(13) . . . . ? C4 O1 C3 C2 -177.07(16) . . . . ? C1 C2 C3 O1 -58.5(2) . . . . ? C9 P1 C5 C6 173.08(12) . . . . ? C13 P1 C5 C6 52.60(14) . . . . ? C1 P1 C5 C6 -67.07(14) . . . . ? P1 C5 C6 C7 159.01(13) . . . . ? C8 O2 C7 C6 -72.97(19) . . . . ? C5 C6 C7 O2 -63.1(2) . . . . ? C5 P1 C9 C10 -74.75(14) . . . . ? C13 P1 C9 C10 45.64(15) . . . . ? C1 P1 C9 C10 165.31(12) . . . . ? P1 C9 C10 C11 178.17(12) . . . . ? C12 O3 C11 C10 178.46(15) . . . . ? C9 C10 C11 O3 -65.72(19) . . . . ? C5 P1 C13 C14 178.46(13) . . . . ? C9 P1 C13 C14 57.79(15) . . . . ? C1 P1 C13 C14 -61.83(15) . . . . ? P1 C13 C14 C15 -160.27(13) . . . . ? C16 O4 C15 C14 179.31(17) . . . . ? C13 C14 C15 O4 60.0(2) . . . . ? _refine_diff_density_max 0.336 _refine_diff_density_min -0.328 _refine_diff_density_rms 0.051 _shelx_res_file ; TITL sh5173_a.res in P2(1)/n sh5173_a.res created by SHELXL-2018/3 at 11:34:17 on 09-Feb-2023 REM Old TITL sh5173 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.137, Rweak 0.005, Alpha 0.026 REM 0.294 for 193 systematic absences, Orientation as input REM Formula found by SHELXT: C16 O4 F6 P2 CELL 0.71073 9.6155 15.4439 15.4444 90.000 93.615 90.000 ZERR 4.000 0.0002 0.0004 0.0004 0.000 0.001 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H O F P UNIT 64 144 16 24 8 TEMP -119.500 SIZE 0.02 0.20 0.20 L.S. 10 BOND ACTA CONF LIST 4 FMAP 2 PLAN -5 WGHT 0.032600 0.764600 FVAR 0.39527 P1 5 0.256828 0.407467 0.152303 11.00000 0.01906 0.01934 = 0.02068 -0.00196 0.00183 -0.00035 O1 3 0.010163 0.191228 0.014321 11.00000 0.03581 0.02614 = 0.03332 -0.00915 -0.00075 -0.00375 O2 3 0.091641 0.473727 -0.115438 11.00000 0.02300 0.02934 = 0.02963 -0.00457 -0.00324 0.00358 O3 3 0.082354 0.597430 0.343922 11.00000 0.03848 0.03927 = 0.02427 -0.00850 0.00270 0.01214 O4 3 0.647647 0.425002 0.305989 11.00000 0.02777 0.03187 = 0.04176 0.00314 -0.00877 -0.00471 C1 1 0.171409 0.307006 0.124617 11.00000 0.02394 0.02063 = 0.02667 -0.00304 0.00125 -0.00170 AFIX 23 H1A 2 0.215457 0.281081 0.074502 11.00000 -1.20000 H1B 2 0.185371 0.266541 0.174118 11.00000 -1.20000 AFIX 0 C2 1 0.014925 0.316967 0.101879 11.00000 0.02354 0.02424 = 0.03281 -0.00503 -0.00030 0.00026 AFIX 23 H2A 2 -0.028937 0.345453 0.150701 11.00000 -1.20000 H2B 2 0.000493 0.354637 0.050228 11.00000 -1.20000 AFIX 0 C3 1 -0.054495 0.230959 0.083620 11.00000 0.02555 0.02714 = 0.03545 -0.00595 -0.00002 -0.00357 AFIX 23 H3A 2 -0.044937 0.193733 0.135841 11.00000 -1.20000 H3B 2 -0.154986 0.239507 0.067965 11.00000 -1.20000 AFIX 0 C4 1 -0.054322 0.111915 -0.009334 11.00000 0.05474 0.03010 = 0.04951 -0.01340 -0.00817 -0.00350 AFIX 137 H4A 2 -0.150666 0.122624 -0.031228 11.00000 -1.50000 H4B 2 -0.053924 0.073900 0.041488 11.00000 -1.50000 H4C 2 -0.003177 0.084118 -0.054695 11.00000 -1.50000 AFIX 0 C5 1 0.227204 0.482493 0.064751 11.00000 0.02193 0.02103 = 0.02278 -0.00090 0.00139 -0.00005 AFIX 23 H5A 2 0.125665 0.487602 0.050651 11.00000 -1.20000 H5B 2 0.262228 0.540199 0.083609 11.00000 -1.20000 AFIX 0 C6 1 0.298156 0.455661 -0.016882 11.00000 0.01665 0.03908 = 0.02419 0.00062 0.00231 0.00294 AFIX 23 H6A 2 0.398033 0.471476 -0.010206 11.00000 -1.20000 H6B 2 0.292041 0.391989 -0.023497 11.00000 -1.20000 AFIX 0 C7 1 0.233085 0.498137 -0.097570 11.00000 0.02203 0.03690 = 0.02485 0.00181 0.00334 0.00140 AFIX 23 H7A 2 0.238345 0.561798 -0.090592 11.00000 -1.20000 H7B 2 0.287213 0.482223 -0.147643 11.00000 -1.20000 AFIX 0 C8 1 0.076976 0.387474 -0.146807 11.00000 0.04242 0.03337 = 0.03310 -0.00749 -0.00568 0.00395 AFIX 137 H8A 2 -0.021592 0.375463 -0.162128 11.00000 -1.50000 H8B 2 0.111846 0.346981 -0.101652 11.00000 -1.50000 H8C 2 0.130561 0.380511 -0.198269 11.00000 -1.50000 AFIX 0 C9 1 0.188174 0.450119 0.248823 11.00000 0.02334 0.02113 = 0.02200 -0.00059 0.00432 -0.00090 AFIX 23 H9A 2 0.093131 0.472491 0.234095 11.00000 -1.20000 H9B 2 0.180179 0.402320 0.290931 11.00000 -1.20000 AFIX 0 C10 1 0.275803 0.522638 0.292388 11.00000 0.02711 0.02454 = 0.02280 -0.00342 0.00071 -0.00330 AFIX 23 H10A 2 0.369926 0.500254 0.309779 11.00000 -1.20000 H10B 2 0.286179 0.570333 0.250454 11.00000 -1.20000 AFIX 0 C11 1 0.209058 0.556982 0.371226 11.00000 0.03473 0.02792 = 0.01984 -0.00213 -0.00189 -0.00117 AFIX 23 H11A 2 0.191485 0.508905 0.411505 11.00000 -1.20000 H11B 2 0.271895 0.599187 0.402036 11.00000 -1.20000 AFIX 0 C12 1 0.011628 0.629457 0.415151 11.00000 0.04662 0.04510 = 0.03696 -0.01746 0.01189 0.00128 AFIX 137 H12A 2 -0.075079 0.657746 0.393760 11.00000 -1.50000 H12B 2 0.071063 0.671431 0.447497 11.00000 -1.50000 H12C 2 -0.009969 0.581322 0.453411 11.00000 -1.50000 AFIX 0 C13 1 0.440401 0.388756 0.170933 11.00000 0.02130 0.02654 = 0.02644 -0.00166 0.00111 -0.00002 AFIX 23 H13A 2 0.476572 0.364623 0.117385 11.00000 -1.20000 H13B 2 0.487336 0.444981 0.182643 11.00000 -1.20000 AFIX 0 C14 1 0.478920 0.327094 0.246396 11.00000 0.02804 0.02424 = 0.03541 0.00347 -0.00271 -0.00137 AFIX 23 H14A 2 0.418441 0.338803 0.294615 11.00000 -1.20000 H14B 2 0.462860 0.266558 0.227191 11.00000 -1.20000 AFIX 0 C15 1 0.629845 0.338296 0.278041 11.00000 0.03079 0.03011 = 0.04283 0.00406 -0.00762 0.00371 AFIX 23 H15A 2 0.653710 0.298065 0.326629 11.00000 -1.20000 H15B 2 0.691437 0.325722 0.230597 11.00000 -1.20000 AFIX 0 C16 1 0.786089 0.442522 0.338154 11.00000 0.03617 0.06251 = 0.06101 0.00195 -0.01917 -0.01269 AFIX 137 H16A 2 0.850187 0.431074 0.292617 11.00000 -1.50000 H16B 2 0.810043 0.405245 0.388240 11.00000 -1.50000 H16C 2 0.793766 0.503361 0.355845 11.00000 -1.50000 AFIX 0 REM PF6 P2 5 0.937941 0.781673 0.612986 11.00000 0.02972 0.02364 = 0.02588 -0.00223 0.00959 -0.00329 F1 4 0.889733 0.818595 0.519632 11.00000 0.05878 0.05140 = 0.03860 0.01260 -0.00520 0.00109 F2 4 0.894043 0.686337 0.582110 11.00000 0.04837 0.02862 = 0.04414 -0.00873 0.01583 -0.01191 F3 4 1.090275 0.766489 0.581115 11.00000 0.03169 0.03241 = 0.05602 -0.00391 0.01479 -0.00050 F4 4 0.980483 0.877340 0.643665 11.00000 0.04809 0.02998 = 0.05621 -0.01587 0.01956 -0.00987 F5 4 0.785586 0.796746 0.645128 11.00000 0.03924 0.04895 = 0.08372 -0.01688 0.03256 -0.00676 F6 4 0.987353 0.744515 0.705848 11.00000 0.08238 0.05985 = 0.02780 0.00878 -0.00129 -0.01149 HKLF 4 REM sh5173_a.res in P2(1)/n REM wR2 = 0.089868, GooF = S = 1.01708, Restrained GooF = 1.01708 for all data REM R1 = 0.038822 for 4021 Fo > 4sig(Fo) and 0.063001 for all 5485 data REM 257 parameters refined using 0 restraints END WGHT 0.0326 0.7646 REM Highest difference peak 0.336, deepest hole -0.328, 1-sigma level 0.051 Q1 1 0.2503 0.4490 0.1001 11.00000 0.05 0.34 Q2 1 0.2127 0.3581 0.1353 11.00000 0.05 0.33 Q3 1 0.2135 0.4226 0.2057 11.00000 0.05 0.31 Q4 1 0.3559 0.3956 0.1617 11.00000 0.05 0.30 Q5 1 0.0855 0.3052 0.1223 11.00000 0.05 0.25 ; _shelx_res_checksum 58938 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_5162_a _database_code_depnum_ccdc_archive 'CCDC 2260786' loop_ _audit_author_name _audit_author_address 'Bernd Morgenstern' ;Universitaet des Saarlandes Germany ; _audit_update_record ; 2023-05-05 deposited with the CCDC. 2023-09-08 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H44 P, F6 P' _chemical_formula_sum 'C20 H44 F6 P2' _chemical_formula_weight 460.49 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' F F 0.0171 0.0103 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 68 _space_group_name_H-M_alt 'C c c a' _space_group_name_Hall '-C 2b 2bc' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1, -y+1/2, z' '-x+1/2, y+1/2, -z+1/2' 'x+1, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' '-x+1/2, -y+1/2, -z' 'x, y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' '-x, y+1/2, z-1/2' _cell_length_a 11.1743(8) _cell_length_b 23.349(2) _cell_length_c 9.9798(6) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2603.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 1679 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 25.91 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.175 _exptl_crystal_F_000 992 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.010 _exptl_absorpt_coefficient_mu 0.213 _shelx_estimated_absorpt_T_min 0.939 _shelx_estimated_absorpt_T_max 0.998 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6467 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 143(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'INCOATEC I\^A?S microfocus sealed tube' _diffrn_measurement_device_type 'Bruker AXS D8 Venture, Photon II' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 7677 _diffrn_reflns_av_unetI/netI 0.0371 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.872 _diffrn_reflns_theta_max 26.728 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.996 _diffrn_reflns_point_group_measured_fraction_full 0.996 _reflns_number_total 1382 _reflns_number_gt 939 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX 4 (Bruker, 2021)' _computing_cell_refinement 'SAINT (Bruker, 2019)' _computing_data_reduction 'SAINT (Bruker, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _computing_structure_refinement ; SHELXL-2018/3 (Sheldrick, 2018), SHELXLe Rev 1000 (Huebschle et al., 2011) ; _computing_molecular_graphics 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_publication_material 'CIFTAB-2014 (Sheldrick, G. M.)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0301P)^2^+2.2142P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 1382 _refine_ls_number_parameters 113 _refine_ls_number_restraints 145 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1018 _refine_ls_wR_factor_gt 0.0889 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.500000 0.750000 0.750000 0.0361(3) Uani 1 4 d S T P . . C1 C 0.4089(2) 0.70567(8) 0.64458(17) 0.0402(5) Uani 1 1 d . . . . . H1A H 0.352595 0.730575 0.594829 0.048 Uiso 1 1 calc R U . . . H1B H 0.461252 0.686777 0.577890 0.048 Uiso 1 1 calc R U . . . C2 C 0.3365(2) 0.65942(8) 0.71716(17) 0.0431(5) Uani 1 1 d . . . . . H2A H 0.391652 0.633986 0.767022 0.052 Uiso 1 1 calc R U . . . H2B H 0.282118 0.677739 0.782706 0.052 Uiso 1 1 calc R U . . . C3 C 0.2634(2) 0.62396(9) 0.61869(19) 0.0472(5) Uani 1 1 d . . . . . H3A H 0.211825 0.649902 0.565582 0.057 Uiso 1 1 calc R U . . . H3B H 0.318544 0.604435 0.555898 0.057 Uiso 1 1 calc R U . . . C4 C 0.1856(2) 0.57948(9) 0.6867(2) 0.0576(6) Uani 1 1 d . . . . . H4A H 0.134842 0.598554 0.754669 0.069 Uiso 1 1 calc R U . . . H4B H 0.237447 0.551585 0.733708 0.069 Uiso 1 1 calc R U . . . C5 C 0.1053(2) 0.54740(11) 0.5875(3) 0.0726(8) Uani 1 1 d . . . . . H5A H 0.048982 0.574336 0.546338 0.109 Uiso 1 1 calc R U . . . H5B H 0.060735 0.517504 0.635002 0.109 Uiso 1 1 calc R U . . . H5C H 0.154872 0.529848 0.517655 0.109 Uiso 1 1 calc R U . . . P1_1 P 0.5024(12) 0.7459(6) 0.2567(14) 0.0407(12) Uani 0.25 1 d D U P A -1 F1_1 F 0.6154(12) 0.7556(6) 0.3508(17) 0.051(4) Uani 0.25 1 d D U P A -1 F2_1 F 0.5193(15) 0.8074(6) 0.1953(17) 0.089(5) Uani 0.25 1 d D U P A -1 F3_1 F 0.3905(17) 0.7366(9) 0.158(2) 0.066(6) Uani 0.25 1 d D U P A -1 F4_1 F 0.4744(14) 0.6870(5) 0.3269(13) 0.074(4) Uani 0.25 1 d D U P A -1 F5_1 F 0.5908(13) 0.7193(9) 0.1482(14) 0.103(6) Uani 0.25 1 d D U P A -1 F6_1 F 0.4204(12) 0.7777(12) 0.3641(16) 0.069(4) Uani 0.25 1 d D U P A -1 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 0.0450(7) 0.0430(6) 0.0202(4) 0.000 0.000 0.000 C1 0.0487(13) 0.0457(11) 0.0262(8) -0.0011(8) -0.0027(9) 0.0011(10) C2 0.0487(13) 0.0491(11) 0.0315(9) -0.0010(8) -0.0068(9) -0.0013(10) C3 0.0459(15) 0.0505(12) 0.0450(11) -0.0112(9) -0.0083(10) 0.0033(11) C4 0.0521(15) 0.0526(13) 0.0680(14) -0.0104(11) -0.0085(13) -0.0059(12) C5 0.0584(18) 0.0734(17) 0.0859(18) -0.0221(14) -0.0153(15) -0.0086(14) P1_1 0.0414(11) 0.062(3) 0.019(2) 0.021(4) 0.008(3) 0.006(5) F1_1 0.047(5) 0.065(10) 0.041(6) -0.007(7) -0.013(4) 0.009(6) F2_1 0.069(11) 0.079(5) 0.118(13) 0.064(6) -0.034(7) -0.038(7) F3_1 0.075(8) 0.078(15) 0.045(6) 0.023(7) -0.026(6) -0.029(8) F4_1 0.108(12) 0.069(5) 0.045(5) 0.020(4) 0.000(7) -0.020(6) F5_1 0.095(10) 0.181(14) 0.033(4) -0.020(11) 0.026(6) 0.015(10) F6_1 0.052(7) 0.106(11) 0.051(5) -0.015(5) -0.005(4) 0.023(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 1.7930(19) 8_466 ? P1 C1 1.7930(19) 3_656 ? P1 C1 1.7930(19) 6_565 ? P1 C1 1.7931(19) . ? C1 C2 1.531(3) . ? C2 C3 1.523(3) . ? C3 C4 1.515(3) . ? C4 C5 1.532(3) . ? P1_1 F2_1 1.571(11) . ? P1_1 F4_1 1.576(10) . ? P1_1 F1_1 1.590(12) . ? P1_1 F5_1 1.593(12) . ? P1_1 F6_1 1.593(12) . ? P1_1 F3_1 1.606(12) . ? 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 C1 108.14(12) 8_466 3_656 ? C1 P1 C1 109.49(13) 8_466 6_565 ? C1 P1 C1 110.79(14) 3_656 6_565 ? C1 P1 C1 110.79(14) 8_466 . ? C1 P1 C1 109.49(13) 3_656 . ? C1 P1 C1 108.14(12) 6_565 . ? C2 C1 P1 115.43(12) . . ? C3 C2 C1 111.19(15) . . ? C4 C3 C2 113.05(16) . . ? C3 C4 C5 112.4(2) . . ? F2_1 P1_1 F4_1 174.1(15) . . ? F2_1 P1_1 F1_1 90.3(9) . . ? F4_1 P1_1 F1_1 91.1(9) . . ? F2_1 P1_1 F5_1 90.9(10) . . ? F4_1 P1_1 F5_1 94.9(13) . . ? F1_1 P1_1 F5_1 88.0(9) . . ? F2_1 P1_1 F6_1 84.7(15) . . ? F4_1 P1_1 F6_1 89.6(12) . . ? F1_1 P1_1 F6_1 89.6(10) . . ? F5_1 P1_1 F6_1 175.0(17) . . ? F2_1 P1_1 F3_1 88.8(9) . . ? F4_1 P1_1 F3_1 89.9(9) . . ? F1_1 P1_1 F3_1 178.5(14) . . ? F5_1 P1_1 F3_1 90.8(10) . . ? F6_1 P1_1 F3_1 91.6(10) . . ? _refine_diff_density_max 0.181 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.039 _shelx_res_file ; TITL 5162_a.res in Ccca 5162_a.res created by SHELXL-2018/3 at 12:41:10 on 02-Feb-2023 REM Old TITL 5162 in Ccca REM SHELXT solution in Ccca: R1 0.254, Rweak 0.007, Alpha 0.038 REM 0.596 for 182 systematic absences, Orientation as input REM Formula found by SHELXT: C14 P CELL 0.71073 11.1743 23.3491 9.9798 90.000 90.000 90.000 ZERR 4.000 0.0008 0.0020 0.0006 0.000 0.000 0.000 LATT 7 SYMM 1/2-X, -Y, Z SYMM -X, Y, 1/2-Z SYMM 1/2+X, -Y, 1/2-Z SFAC C H F P UNIT 80 176 24 8 SADI_PF6 P1 F1 P1 F2 P1 F3 P1 F4 P1 F5 P1 F6 SADI_PF6 0.04 F1 F2 F1 F4 F1 F5 F1 F6 F3 F2 F3 F4 F3 F5 F3 F6 SADI_PF6 0.05 F1 F3 F2 F4 F6 F5 SIMU_PF6 P1 > F6 RIGU_PF6 P1 > F6 SAME_PF6 P1 > F6 SIMU 0.04 0.08 1 TEMP -130.150 SHEL 10000 0.79 SIZE 0.01 0.18 0.30 L.S. 10 OMIT 3 3 6 BOND ACTA LIST 4 FMAP 2 PLAN -5 WGHT 0.030100 2.214200 FVAR 0.34763 P1 4 0.500000 0.750000 0.750000 10.25000 0.04504 0.04300 = 0.02019 0.00000 0.00000 0.00000 C1 1 0.408875 0.705671 0.644577 11.00000 0.04870 0.04568 = 0.02624 -0.00105 -0.00273 0.00108 AFIX 23 H1A 2 0.352595 0.730575 0.594829 11.00000 -1.20000 H1B 2 0.461252 0.686777 0.577890 11.00000 -1.20000 AFIX 0 C2 1 0.336503 0.659421 0.717162 11.00000 0.04869 0.04909 = 0.03152 -0.00101 -0.00677 -0.00127 AFIX 23 H2A 2 0.391652 0.633986 0.767022 11.00000 -1.20000 H2B 2 0.282118 0.677739 0.782706 11.00000 -1.20000 AFIX 0 C3 1 0.263408 0.623959 0.618691 11.00000 0.04593 0.05055 = 0.04504 -0.01116 -0.00830 0.00330 AFIX 23 H3A 2 0.211825 0.649902 0.565582 11.00000 -1.20000 H3B 2 0.318544 0.604435 0.555898 11.00000 -1.20000 AFIX 0 C4 1 0.185594 0.579481 0.686696 11.00000 0.05212 0.05263 = 0.06805 -0.01036 -0.00849 -0.00592 AFIX 23 H4A 2 0.134842 0.598554 0.754669 11.00000 -1.20000 H4B 2 0.237447 0.551585 0.733708 11.00000 -1.20000 AFIX 0 C5 1 0.105318 0.547404 0.587491 11.00000 0.05840 0.07340 = 0.08591 -0.02212 -0.01528 -0.00858 AFIX 137 H5A 2 0.048982 0.574336 0.546338 11.00000 -1.50000 H5B 2 0.060735 0.517504 0.635002 11.00000 -1.50000 H5C 2 0.154872 0.529848 0.517655 11.00000 -1.50000 AFIX 0 PART -1 RESI PF6 1 P1 4 0.502409 0.745946 0.256704 10.25000 0.04139 0.06169 = 0.01899 0.02116 0.00787 0.00560 F1 3 0.615362 0.755643 0.350849 10.25000 0.04685 0.06482 = 0.04146 -0.00723 -0.01267 0.00885 F2 3 0.519346 0.807354 0.195304 10.25000 0.06880 0.07920 = 0.11844 0.06437 -0.03376 -0.03771 F3 3 0.390464 0.736559 0.158201 10.25000 0.07492 0.07769 = 0.04527 0.02292 -0.02613 -0.02908 F4 3 0.474417 0.686994 0.326922 10.25000 0.10812 0.06924 = 0.04469 0.02007 0.00023 -0.01969 F5 3 0.590846 0.719333 0.148161 10.25000 0.09539 0.18102 = 0.03331 -0.02011 0.02551 0.01497 F6 3 0.420420 0.777650 0.364105 10.25000 0.05159 0.10583 = 0.05097 -0.01508 -0.00515 0.02274 RESI 0 HKLF 4 REM 5162_a.res in Ccca REM wR2 = 0.101783, GooF = S = 1.05326, Restrained GooF = 1.02815 for all data REM R1 = 0.042332 for 939 Fo > 4sig(Fo) and 0.073622 for all 1382 data REM 113 parameters refined using 145 restraints END WGHT 0.0301 2.2145 REM Highest difference peak 0.181, deepest hole -0.199, 1-sigma level 0.039 Q1 1 0.3596 0.8090 0.8113 11.00000 0.05 0.18 Q2 1 0.0050 0.5416 0.6087 11.00000 0.05 0.15 Q3 1 0.7026 0.7500 0.7500 10.50000 0.05 0.14 Q4 1 0.5777 0.7305 0.8099 11.00000 0.05 0.14 Q5 1 -0.0422 0.5584 0.4495 11.00000 0.05 0.13 ; _shelx_res_checksum 64111 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_TW2109_bm _database_code_depnum_ccdc_archive 'CCDC 2260790' loop_ _audit_author_name _audit_author_address 'Bernd Morgenstern' ;Universitaet des Saarlandes Germany ; _audit_update_record ; 2023-05-05 deposited with the CCDC. 2023-09-08 downloaded from the CCDC. ; # start Validation Reply Form _vrf_PLAT915_TW2109_bm ; PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage 37 % RESPONSE: The presence of one atom of significantly higher atomic number than anything else in the structure (i.e. the bromine) allows for an unambiguous determination of the absolute structure without requiring Friedel opposites. ; # end Validation Reply Form _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H36 O4 P, Br' _chemical_formula_sum 'C16 H36 Br O4 P' _chemical_formula_weight 403.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 5 _space_group_name_H-M_alt 'C 2' _space_group_name_Hall 'C 2y' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 22.6790(12) _cell_length_b 5.6876(3) _cell_length_c 8.1653(4) _cell_angle_alpha 90 _cell_angle_beta 99.864(5) _cell_angle_gamma 90 _cell_volume 1037.66(9) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 934 _cell_measurement_theta_min 3.3420 _cell_measurement_theta_max 26.7120 _exptl_crystal_description needles _exptl_crystal_colour Colourless _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.291 _exptl_crystal_F_000 428 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.070 _exptl_absorpt_coefficient_mu 2.071 _shelx_estimated_absorpt_T_min 0.575 _shelx_estimated_absorpt_T_max 0.869 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.787 _exptl_absorpt_correction_T_max 0.898 _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'Enhance (Mo) X-ray Source' _diffrn_measurement_device_type 'Agilent Xcalibur 3 E' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean 16.0382 _diffrn_reflns_number 1722 _diffrn_reflns_av_unetI/netI 0.0262 _diffrn_reflns_av_R_equivalents 0.0118 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.532 _diffrn_reflns_theta_max 25.008 _diffrn_reflns_theta_full 25.008 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_Laue_measured_fraction_full 0.988 _diffrn_reflns_point_group_measured_fraction_max 0.714 _diffrn_reflns_point_group_measured_fraction_full 0.714 _reflns_number_total 1309 _reflns_number_gt 1269 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.301 _reflns_Friedel_fraction_max 0.371 _reflns_Friedel_fraction_full 0.371 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'CrysAlisPro, Rigaku OD' _computing_cell_refinement 'CrysAlisPro, Rigaku OD' _computing_data_reduction 'CrysAlisPro, Rigaku OD' _computing_structure_solution 'SHELXS-2014 (Sheldrick, 2017)' _computing_structure_refinement ; SHELXL-2018/3 (Sheldrick, 2018), SHELXLe Rev 1000 (Huebschle et al., 2011) ; _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'CIFTAB-2014 (Sheldrick, 2017)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0238P)^2^+0.2240P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_abs_structure_details ; Classical Flack method preferred over Parsons because s.u. lower. ; _refine_ls_abs_structure_Flack -0.019(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 1309 _refine_ls_number_parameters 103 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0219 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0479 _refine_ls_wR_factor_gt 0.0471 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 Br1 Br 0.500000 0.97540(2) 1.000000 0.03502(16) Uani 1 2 d S T P . . O1 O 0.33111(11) 0.8350(5) 0.5895(3) 0.0410(6) Uani 1 1 d . . . . . C1 C 0.45200(14) 0.6805(6) 0.5983(4) 0.0262(7) Uani 1 1 d . . . . . H1A H 0.476903 0.772018 0.687503 0.031 Uiso 1 1 calc R U . . . H1B H 0.431517 0.793612 0.515380 0.031 Uiso 1 1 calc R U . . . P1 P 0.500000 0.4977(3) 0.500000 0.0205(3) Uani 1 2 d S T P . . C2 C 0.40483(13) 0.5454(6) 0.6729(4) 0.0346(9) Uani 1 1 d . . . . . H2A H 0.383402 0.436014 0.588831 0.042 Uiso 1 1 calc R U . . . H2B H 0.424634 0.451206 0.768696 0.042 Uiso 1 1 calc R U . . . O2 O 0.33477(11) 0.1597(5) 0.2300(3) 0.0430(6) Uani 1 1 d . . . . . C3 C 0.36058(14) 0.7123(7) 0.7294(4) 0.0354(8) Uani 1 1 d . . . . . H3A H 0.331192 0.623399 0.781816 0.042 Uiso 1 1 calc R U . . . H3B H 0.381709 0.824050 0.812242 0.042 Uiso 1 1 calc R U . . . C5 C 0.45493(14) 0.3140(6) 0.3499(4) 0.0272(7) Uani 1 1 d . . . . . H5A H 0.481442 0.224551 0.287993 0.033 Uiso 1 1 calc R U . . . H5B H 0.433314 0.199160 0.408956 0.033 Uiso 1 1 calc R U . . . C4 C 0.29194(15) 1.0095(9) 0.6317(5) 0.0504(12) Uani 1 1 d . . . . . H4A H 0.273542 1.093591 0.531076 0.076 Uiso 1 1 calc R U . . . H4B H 0.314496 1.120759 0.710235 0.076 Uiso 1 1 calc R U . . . H4C H 0.260633 0.935310 0.683078 0.076 Uiso 1 1 calc R U . . . C6 C 0.40927(12) 0.4515(9) 0.2256(3) 0.0343(7) Uani 1 1 d . . . . . H6A H 0.386739 0.560688 0.286406 0.041 Uiso 1 1 calc R U . . . H6B H 0.430456 0.545822 0.151861 0.041 Uiso 1 1 calc R U . . . C8 C 0.29947(14) -0.0229(12) 0.1491(4) 0.0505(8) Uani 1 1 d . . . . . H8A H 0.279786 -0.106918 0.229585 0.076 Uiso 1 1 calc R U . . . H8B H 0.324921 -0.132166 0.099902 0.076 Uiso 1 1 calc R U . . . H8C H 0.269080 0.043186 0.061326 0.076 Uiso 1 1 calc R U . . . C7 C 0.36624(15) 0.2841(7) 0.1222(4) 0.0349(8) Uani 1 1 d . . . . . H7A H 0.337821 0.372945 0.039219 0.042 Uiso 1 1 calc R U . . . H7B H 0.388530 0.172875 0.062282 0.042 Uiso 1 1 calc R U . . . 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 Br1 0.0350(2) 0.0453(3) 0.0249(2) 0.000 0.00580(17) 0.000 O1 0.0380(14) 0.0504(16) 0.0343(13) -0.0021(12) 0.0050(11) 0.0142(12) C1 0.0300(17) 0.0247(17) 0.0257(16) -0.0028(14) 0.0101(13) -0.0005(14) P1 0.0230(5) 0.0190(8) 0.0201(4) 0.000 0.0051(4) 0.000 C2 0.0320(16) 0.038(2) 0.0372(17) 0.0082(15) 0.0165(15) 0.0018(15) O2 0.0404(14) 0.0524(17) 0.0387(14) -0.0113(13) 0.0140(12) -0.0175(12) C3 0.0308(18) 0.046(2) 0.0320(18) 0.0023(17) 0.0139(15) -0.0013(17) C5 0.0290(17) 0.0282(18) 0.0230(16) -0.0011(14) 0.0006(13) -0.0006(14) C4 0.0423(19) 0.045(3) 0.065(2) -0.002(2) 0.0130(17) 0.011(2) C6 0.0331(15) 0.0372(19) 0.0297(14) 0.007(2) -0.0032(12) -0.003(2) C8 0.0396(17) 0.051(2) 0.0581(19) -0.006(3) 0.0000(15) -0.009(3) C7 0.0293(18) 0.045(2) 0.0276(18) 0.0039(16) -0.0021(15) -0.0015(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 C3 1.406(4) . ? O1 C4 1.414(5) . ? C1 C2 1.526(4) . ? C1 P1 1.791(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? P1 C5 1.791(3) . ? P1 C5 1.791(3) 2_656 ? C2 C3 1.510(4) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? O2 C8 1.405(6) . ? O2 C7 1.414(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C5 C6 1.535(5) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C6 C7 1.513(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? 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 C3 O1 C4 112.4(2) . . ? C2 C1 P1 114.1(2) . . ? C2 C1 H1A 108.7 . . ? P1 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? P1 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C5 P1 C5 108.6(2) . 2_656 ? C5 P1 C1 109.00(14) . . ? C5 P1 C1 110.58(15) 2_656 . ? C5 P1 C1 110.58(15) . 2_656 ? C5 P1 C1 109.00(14) 2_656 2_656 ? C1 P1 C1 109.0(2) . 2_656 ? C3 C2 C1 110.7(3) . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C8 O2 C7 112.6(3) . . ? O1 C3 C2 108.2(3) . . ? O1 C3 H3A 110.1 . . ? C2 C3 H3A 110.1 . . ? O1 C3 H3B 110.1 . . ? C2 C3 H3B 110.1 . . ? H3A C3 H3B 108.4 . . ? C6 C5 P1 113.4(3) . . ? C6 C5 H5A 108.9 . . ? P1 C5 H5A 108.9 . . ? C6 C5 H5B 108.9 . . ? P1 C5 H5B 108.9 . . ? H5A C5 H5B 107.7 . . ? O1 C4 H4A 109.5 . . ? O1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? O1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C7 C6 C5 110.2(4) . . ? C7 C6 H6A 109.6 . . ? C5 C6 H6A 109.6 . . ? C7 C6 H6B 109.6 . . ? C5 C6 H6B 109.6 . . ? H6A C6 H6B 108.1 . . ? O2 C8 H8A 109.5 . . ? O2 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O2 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O2 C7 C6 108.3(3) . . ? O2 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? O2 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? 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 C2 C1 P1 C5 53.8(3) . . . . ? C2 C1 P1 C5 -65.6(3) . . . 2_656 ? C2 C1 P1 C1 174.6(3) . . . 2_656 ? P1 C1 C2 C3 -171.3(2) . . . . ? C4 O1 C3 C2 -175.3(3) . . . . ? C1 C2 C3 O1 62.0(4) . . . . ? C5 P1 C5 C6 173.6(3) 2_656 . . . ? C1 P1 C5 C6 53.1(3) . . . . ? C1 P1 C5 C6 -66.8(3) 2_656 . . . ? P1 C5 C6 C7 -170.5(2) . . . . ? C8 O2 C7 C6 -171.9(4) . . . . ? C5 C6 C7 O2 61.9(3) . . . . ? _refine_diff_density_max 0.207 _refine_diff_density_min -0.204 _refine_diff_density_rms 0.039 _shelx_res_file ; TITL tw2109_a.res in C2 TW2109_bm.res created by SHELXL-2018/3 at 12:32:49 on 01-Mar-2023 REM Old TITL TW2109 in C2 REM SHELXT solution in C2: R1 0.103, Rweak 0.065, Alpha 0.033 REM 0.000 for 0 systematic absences, Orientation as input REM Flack x = 0.032 ( 0.012 ) from 301 Parsons' quotients REM Formula found by SHELXT: C16 O4 P Br CELL 0.71073 22.679 5.6876 8.1653 90 99.864 90 ZERR 2 0.0012 0.0003 0.0004 0 0.005 0 LATT -7 SYMM -X,+Y,-Z SFAC Br C O P H UNIT 2 32 8 2 72 L.S. 10 PLAN 10 CONF SIZE 0.07 0.1 0.3 TEMP -100 ACTA list 4 MORE -1 SHEL 10000 0.84 BOND $H WGHT 0.023800 0.224000 FVAR 0.58990 BR1 1 0.500000 0.975404 1.000000 10.50000 0.03503 0.04535 = 0.02494 0.00000 0.00580 0.00000 O1 3 0.331112 0.835003 0.589532 11.00000 0.03799 0.05043 = 0.03427 -0.00206 0.00498 0.01420 C1 2 0.452003 0.680473 0.598250 11.00000 0.02997 0.02473 = 0.02567 -0.00275 0.01013 -0.00046 AFIX 23 H1A 5 0.476903 0.772018 0.687503 11.00000 -1.20000 H1B 5 0.431517 0.793612 0.515380 11.00000 -1.20000 AFIX 0 P1 4 0.500000 0.497674 0.500000 10.50000 0.02301 0.01897 = 0.02009 0.00000 0.00510 0.00000 C2 2 0.404834 0.545387 0.672899 11.00000 0.03197 0.03843 = 0.03717 0.00816 0.01651 0.00184 AFIX 23 H2A 5 0.383402 0.436014 0.588831 11.00000 -1.20000 H2B 5 0.424634 0.451206 0.768696 11.00000 -1.20000 AFIX 0 O2 3 0.334768 0.159672 0.230012 11.00000 0.04044 0.05236 = 0.03871 -0.01130 0.01402 -0.01747 C3 2 0.360576 0.712261 0.729436 11.00000 0.03076 0.04628 = 0.03204 0.00228 0.01392 -0.00127 AFIX 23 H3A 5 0.331192 0.623399 0.781816 11.00000 -1.20000 H3B 5 0.381709 0.824050 0.812242 11.00000 -1.20000 AFIX 0 C5 2 0.454935 0.313979 0.349937 11.00000 0.02902 0.02815 = 0.02302 -0.00109 0.00059 -0.00065 AFIX 23 H5A 5 0.481442 0.224551 0.287993 11.00000 -1.20000 H5B 5 0.433314 0.199160 0.408956 11.00000 -1.20000 AFIX 0 C4 2 0.291942 1.009550 0.631715 11.00000 0.04227 0.04504 = 0.06509 -0.00227 0.01299 0.01067 AFIX 137 H4A 5 0.273542 1.093591 0.531076 11.00000 -1.50000 H4B 5 0.314496 1.120759 0.710235 11.00000 -1.50000 H4C 5 0.260633 0.935310 0.683078 11.00000 -1.50000 AFIX 0 C6 2 0.409266 0.451522 0.225585 11.00000 0.03306 0.03718 = 0.02966 0.00672 -0.00323 -0.00339 AFIX 23 H6A 5 0.386739 0.560688 0.286406 11.00000 -1.20000 H6B 5 0.430456 0.545822 0.151861 11.00000 -1.20000 AFIX 0 C8 2 0.299469 -0.022860 0.149086 11.00000 0.03959 0.05083 = 0.05806 -0.00558 -0.00001 -0.00939 AFIX 137 H8A 5 0.279786 -0.106918 0.229585 11.00000 -1.50000 H8B 5 0.324921 -0.132166 0.099902 11.00000 -1.50000 H8C 5 0.269080 0.043186 0.061326 11.00000 -1.50000 AFIX 0 C7 2 0.366236 0.284112 0.122206 11.00000 0.02930 0.04530 = 0.02764 0.00388 -0.00208 -0.00145 AFIX 23 H7A 5 0.337821 0.372945 0.039219 11.00000 -1.20000 H7B 5 0.388530 0.172875 0.062282 11.00000 -1.20000 AFIX 0 HKLF 4 REM tw2109_a.res in C2 REM wR2 = 0.047852, GooF = S = 1.04461, Restrained GooF = 1.04418 for all data REM R1 = 0.020540 for 1269 Fo > 4sig(Fo) and 0.021942 for all 1309 data REM 103 parameters refined using 1 restraints END WGHT 0.0238 0.2240 REM Highest difference peak 0.207, deepest hole -0.204, 1-sigma level 0.039 Q1 1 0.4907 1.0687 0.8859 11.00000 0.05 0.21 Q2 1 0.5106 0.8771 1.1158 11.00000 0.05 0.20 Q3 1 0.4682 0.5860 0.5512 11.00000 0.05 0.19 Q4 1 0.5371 0.9573 0.9423 11.00000 0.05 0.17 Q5 1 0.4678 0.7107 0.1287 11.00000 0.05 0.17 Q6 1 0.4995 0.7757 0.9765 11.00000 0.05 0.16 Q7 1 0.4958 0.8393 0.9212 11.00000 0.05 0.15 Q8 1 0.4314 0.6036 0.6359 11.00000 0.05 0.14 Q9 1 0.4012 0.9710 0.7797 11.00000 0.05 0.13 Q10 1 0.4659 0.7203 0.8064 11.00000 0.05 0.13 ; _shelx_res_checksum 2229 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_5209_a _database_code_depnum_ccdc_archive 'CCDC 2260787' loop_ _audit_author_name _audit_author_address 'Bernd Morgenstern' ;Universitaet des Saarlandes Germany ; _audit_update_record ; 2023-05-05 deposited with the CCDC. 2023-09-08 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H44 P, B F4' _chemical_formula_sum 'C20 H44 B F4 P' _chemical_formula_weight 402.33 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' B B 0.0013 0.0007 '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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 54 _space_group_name_H-M_alt 'P c c a' _space_group_name_Hall '-P 2a 2ac' _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. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z' '-x, y, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z' 'x, -y, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 23.535(4) _cell_length_b 10.8949(17) _cell_length_c 9.5632(15) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2452.1(7) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 4694 _cell_measurement_theta_min 2.55 _cell_measurement_theta_max 27.14 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.090 _exptl_crystal_F_000 880 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.400 _exptl_crystal_size_min 0.040 _exptl_absorpt_coefficient_mu 0.144 _shelx_estimated_absorpt_T_min 0.945 _shelx_estimated_absorpt_T_max 0.994 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5928 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 143(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'INCOATEC I\^A?S microfocus sealed tube' _diffrn_measurement_device_type 'Bruker AXS D8 Venture, Photon II' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19707 _diffrn_reflns_av_unetI/netI 0.0346 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.548 _diffrn_reflns_theta_max 25.677 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measured_fraction_theta_full 0.982 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_Laue_measured_fraction_full 0.982 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_point_group_measured_fraction_full 0.982 _reflns_number_total 2289 _reflns_number_gt 1757 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX 4 (Bruker, 2021)' _computing_cell_refinement 'SAINT (Bruker, 2019)' _computing_data_reduction 'SAINT (Bruker, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _computing_structure_refinement ; SHELXL-2018/3 (Sheldrick, 2018), SHELXLe Rev 1000 (Huebschle et al., 2011) ; _computing_molecular_graphics 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_publication_material 'CIFTAB-2014 (Sheldrick, G. M.)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0201P)^2^+3.2134P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 2289 _refine_ls_number_parameters 176 _refine_ls_number_restraints 66 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0679 _refine_ls_wR_factor_ref 0.1476 _refine_ls_wR_factor_gt 0.1367 _refine_ls_goodness_of_fit_ref 1.219 _refine_ls_restrained_S_all 1.203 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.500000 0.75789(10) 0.750000 0.0301(3) Uani 1 2 d S T P . . C1 C 0.53772(11) 0.6641(3) 0.6264(3) 0.0330(7) Uani 1 1 d . . . . . H1A H 0.510553 0.606504 0.582357 0.040 Uiso 1 1 calc R U . . . H1B H 0.553172 0.717512 0.551794 0.040 Uiso 1 1 calc R U . . . C2 C 0.58672(12) 0.5899(3) 0.6905(3) 0.0336(7) Uani 1 1 d . . . . . H2A H 0.614273 0.646735 0.734373 0.040 Uiso 1 1 calc R U . . . H2B H 0.571621 0.535213 0.764315 0.040 Uiso 1 1 calc R U . . . C3 C 0.61695(11) 0.5131(3) 0.5800(3) 0.0344(7) Uani 1 1 d . . . . . H3A H 0.589518 0.454439 0.538861 0.041 Uiso 1 1 calc R U . . . H3B H 0.630342 0.567829 0.504206 0.041 Uiso 1 1 calc R U . . . C4 C 0.66725(13) 0.4423(3) 0.6381(3) 0.0427(8) Uani 1 1 d . . . . . H4A H 0.653960 0.388988 0.715322 0.051 Uiso 1 1 calc R U . . . H4B H 0.695023 0.501152 0.677480 0.051 Uiso 1 1 calc R U . . . C5 C 0.69680(14) 0.3635(3) 0.5290(3) 0.0511(9) Uani 1 1 d . . . . . H5A H 0.730227 0.324327 0.570810 0.077 Uiso 1 1 calc R U . . . H5B H 0.708688 0.415071 0.450367 0.077 Uiso 1 1 calc R U . . . H5C H 0.670530 0.300144 0.495564 0.077 Uiso 1 1 calc R U . . . C6 C 0.54904(11) 0.8521(3) 0.8450(3) 0.0333(7) Uani 1 1 d . . . . . H6A H 0.527061 0.909709 0.904050 0.040 Uiso 1 1 calc R U . . . H6B H 0.571351 0.798796 0.908356 0.040 Uiso 1 1 calc R U . . . C7 C 0.59051(11) 0.9267(3) 0.7553(3) 0.0350(6) Uani 1 1 d . . . . . H7A H 0.612907 0.870366 0.695617 0.042 Uiso 1 1 calc R U . . . H7B H 0.568866 0.982498 0.693323 0.042 Uiso 1 1 calc R U . . . C8 C 0.63066(12) 1.0017(3) 0.8467(3) 0.0399(7) Uani 1 1 d . . . . . H8A H 0.607872 1.055691 0.908285 0.048 Uiso 1 1 calc R U . . . H8B H 0.652562 0.945138 0.907171 0.048 Uiso 1 1 calc R U . . . C9 C 0.67181(13) 1.0800(3) 0.7636(3) 0.0481(8) Uani 1 1 d . . . . . H9A H 0.650091 1.133638 0.699428 0.058 Uiso 1 1 calc R U . . . H9B H 0.696238 1.025910 0.706142 0.058 Uiso 1 1 calc R U . . . C10 C 0.70925(15) 1.1593(4) 0.8572(4) 0.0624(11) Uani 1 1 d . . . . . H10A H 0.735991 1.205901 0.799236 0.094 Uiso 1 1 calc R U . . . H10B H 0.730433 1.106729 0.921921 0.094 Uiso 1 1 calc R U . . . H10C H 0.685404 1.216332 0.910431 0.094 Uiso 1 1 calc R U . . . B1 B 0.500000 0.2410(6) 0.750000 0.0520(14) Uani 1 2 d S T P . . F1_1 F 0.5562(6) 0.2623(14) 0.703(3) 0.095(9) Uani 0.283(11) 1 d D . P A -1 F2_1 F 0.4791(11) 0.162(2) 0.636(3) 0.071(10) Uani 0.283(11) 1 d D . P A -1 F3_1 F 0.5068(13) 0.153(2) 0.860(3) 0.062(10) Uani 0.283(11) 1 d D . P A -1 F4_1 F 0.4713(9) 0.3268(14) 0.773(3) 0.133(9) Uani 0.283(11) 1 d D . P A -1 F1_2 F 0.5566(6) 0.2626(19) 0.800(2) 0.074(6) Uani 0.217(11) 1 d D . P A -2 F2_2 F 0.4883(12) 0.3700(13) 0.6955(19) 0.075(6) Uani 0.217(11) 1 d D . P A -2 F3_2 F 0.4984(13) 0.172(2) 0.646(2) 0.062(11) Uani 0.217(11) 1 d D . P A -2 F4_2 F 0.4660(10) 0.229(3) 0.8566(14) 0.087(10) Uani 0.217(11) 1 d D . 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 0.0330(5) 0.0322(6) 0.0251(5) 0.000 0.0000(4) 0.000 C1 0.0369(15) 0.0379(18) 0.0242(13) 0.0000(12) -0.0006(11) 0.0021(13) C2 0.0431(15) 0.0295(16) 0.0280(13) 0.0014(12) -0.0008(12) 0.0034(13) C3 0.0441(15) 0.0327(17) 0.0262(14) -0.0013(13) 0.0022(12) 0.0025(13) C4 0.0482(17) 0.0405(19) 0.0394(17) -0.0062(14) 0.0010(14) 0.0086(14) C5 0.0527(19) 0.052(2) 0.049(2) -0.0103(17) 0.0057(16) 0.0106(16) C6 0.0389(15) 0.0347(17) 0.0264(14) -0.0005(12) -0.0013(11) -0.0011(13) C7 0.0378(14) 0.0355(16) 0.0317(14) -0.0003(14) -0.0006(13) -0.0041(12) C8 0.0427(15) 0.0374(18) 0.0395(16) -0.0027(14) -0.0072(13) -0.0050(14) C9 0.0504(18) 0.044(2) 0.0499(19) 0.0032(17) -0.0087(15) -0.0143(15) C10 0.061(2) 0.050(2) 0.077(3) 0.002(2) -0.0230(19) -0.0178(18) B1 0.056(3) 0.063(4) 0.037(3) 0.000 -0.001(3) 0.000 F1_1 0.071(9) 0.078(11) 0.13(2) 0.044(15) 0.009(10) -0.031(7) F2_1 0.100(16) 0.072(16) 0.040(11) 0.012(9) -0.038(10) -0.051(13) F3_1 0.10(2) 0.058(13) 0.032(12) 0.001(9) 0.025(11) -0.026(15) F4_1 0.16(2) 0.049(12) 0.19(3) -0.002(19) 0.03(2) 0.073(14) F1_2 0.064(8) 0.117(16) 0.041(8) -0.006(9) -0.010(6) 0.019(9) F2_2 0.130(14) 0.036(9) 0.059(7) 0.004(6) -0.018(8) 0.016(10) F3_2 0.09(3) 0.057(14) 0.040(11) -0.010(9) -0.042(16) -0.004(17) F4_2 0.095(18) 0.14(3) 0.023(7) -0.007(10) 0.016(9) -0.057(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C6 1.792(3) 3_656 ? P1 C6 1.792(3) . ? P1 C1 1.797(3) . ? P1 C1 1.797(3) 3_656 ? C1 C2 1.536(4) . ? C2 C3 1.524(4) . ? C3 C4 1.518(4) . ? C4 C5 1.520(4) . ? C6 C7 1.533(4) . ? C7 C8 1.525(4) . ? C8 C9 1.515(4) . ? C9 C10 1.524(4) . ? B1 F4_1 1.175(12) . ? B1 F3_2 1.244(19) . ? B1 F4_2 1.301(13) . ? B1 F1_1 1.414(12) . ? B1 F3_1 1.43(2) . ? B1 F1_2 1.433(11) . ? B1 F2_1 1.48(2) . ? B1 F2_2 1.524(14) . ? 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 C6 P1 C6 110.1(2) 3_656 . ? C6 P1 C1 108.08(12) 3_656 . ? C6 P1 C1 109.94(13) . . ? C6 P1 C1 109.94(13) 3_656 3_656 ? C6 P1 C1 108.09(12) . 3_656 ? C1 P1 C1 110.7(2) . 3_656 ? C2 C1 P1 114.08(18) . . ? C3 C2 C1 111.3(2) . . ? C4 C3 C2 112.9(2) . . ? C3 C4 C5 113.1(3) . . ? C7 C6 P1 115.46(19) . . ? C8 C7 C6 111.0(2) . . ? C9 C8 C7 113.4(3) . . ? C8 C9 C10 112.4(3) . . ? F3_2 B1 F4_2 123.2(15) . . ? F4_1 B1 F1_1 117.8(14) . . ? F4_1 B1 F3_1 117.3(14) . . ? F1_1 B1 F3_1 103.8(13) . . ? F3_2 B1 F1_2 113.0(14) . . ? F4_2 B1 F1_2 109.1(7) . . ? F4_1 B1 F2_1 114.4(15) . . ? F1_1 B1 F2_1 100.0(11) . . ? F3_1 B1 F2_1 100.8(10) . . ? F3_2 B1 F2_2 106.2(12) . . ? F4_2 B1 F2_2 104.3(13) . . ? F1_2 B1 F2_2 97.5(10) . . ? _refine_diff_density_max 0.192 _refine_diff_density_min -0.349 _refine_diff_density_rms 0.046 _shelx_res_file ; TITL 5209_a.res in Pcca 5209_a.res created by SHELXL-2018/3 at 12:11:48 on 24-Mar-2023 REM Old TITL 5209 in Pcca REM SHELXT solution in Pcca: R1 0.228, Rweak 0.013, Alpha 0.051 REM 0.914 for 339 systematic absences, Orientation as input REM Formula found by SHELXT: C27 P CELL 0.71073 23.5345 10.8949 9.5632 90.000 90.000 90.000 ZERR 4.000 0.0036 0.0017 0.0015 0.000 0.000 0.000 LATT 1 SYMM 1/2-X, -Y, Z SYMM -X, Y, 1/2-Z SYMM 1/2+X, -Y, 1/2-Z SFAC C H B F P UNIT 80 176 4 16 4 TEMP -130.150 SIZE 0.04 0.40 0.40 L.S. 10 BOND SHEL 10000 0.82 ACTA LIST 4 FMAP 2 PLAN -5 WGHT 0.020100 3.213400 FVAR 0.67419 0.56591 P1 5 0.500000 0.757892 0.750000 10.50000 0.03304 0.03222 = 0.02510 0.00000 0.00003 0.00000 C1 1 0.537724 0.664094 0.626413 11.00000 0.03692 0.03795 = 0.02420 0.00002 -0.00065 0.00212 AFIX 23 H1A 2 0.510553 0.606504 0.582357 11.00000 -1.20000 H1B 2 0.553172 0.717512 0.551794 11.00000 -1.20000 AFIX 0 C2 1 0.586723 0.589901 0.690466 11.00000 0.04311 0.02953 = 0.02804 0.00140 -0.00081 0.00342 AFIX 23 H2A 2 0.614273 0.646735 0.734373 11.00000 -1.20000 H2B 2 0.571621 0.535213 0.764315 11.00000 -1.20000 AFIX 0 C3 1 0.616945 0.513116 0.579998 11.00000 0.04413 0.03272 = 0.02620 -0.00125 0.00221 0.00245 AFIX 23 H3A 2 0.589518 0.454439 0.538861 11.00000 -1.20000 H3B 2 0.630342 0.567829 0.504206 11.00000 -1.20000 AFIX 0 C4 1 0.667247 0.442298 0.638127 11.00000 0.04819 0.04048 = 0.03939 -0.00621 0.00103 0.00864 AFIX 23 H4A 2 0.653960 0.388988 0.715322 11.00000 -1.20000 H4B 2 0.695023 0.501152 0.677480 11.00000 -1.20000 AFIX 0 C5 1 0.696797 0.363459 0.529029 11.00000 0.05269 0.05211 = 0.04851 -0.01032 0.00570 0.01062 AFIX 137 H5A 2 0.730227 0.324327 0.570810 11.00000 -1.50000 H5B 2 0.708688 0.415071 0.450367 11.00000 -1.50000 H5C 2 0.670530 0.300144 0.495564 11.00000 -1.50000 AFIX 0 C6 1 0.549037 0.852107 0.845013 11.00000 0.03887 0.03472 = 0.02640 -0.00049 -0.00132 -0.00106 AFIX 23 H6A 2 0.527061 0.909709 0.904050 11.00000 -1.20000 H6B 2 0.571351 0.798796 0.908356 11.00000 -1.20000 AFIX 0 C7 1 0.590512 0.926704 0.755281 11.00000 0.03778 0.03545 = 0.03167 -0.00028 -0.00058 -0.00414 AFIX 23 H7A 2 0.612907 0.870366 0.695617 11.00000 -1.20000 H7B 2 0.568866 0.982498 0.693323 11.00000 -1.20000 AFIX 0 C8 1 0.630658 1.001720 0.846707 11.00000 0.04271 0.03741 = 0.03949 -0.00273 -0.00723 -0.00495 AFIX 23 H8A 2 0.607872 1.055691 0.908285 11.00000 -1.20000 H8B 2 0.652562 0.945138 0.907171 11.00000 -1.20000 AFIX 0 C9 1 0.671807 1.079982 0.763648 11.00000 0.05037 0.04403 = 0.04992 0.00316 -0.00868 -0.01435 AFIX 23 H9A 2 0.650091 1.133638 0.699428 11.00000 -1.20000 H9B 2 0.696238 1.025910 0.706142 11.00000 -1.20000 AFIX 0 C10 1 0.709251 1.159318 0.857156 11.00000 0.06083 0.04955 = 0.07690 0.00163 -0.02299 -0.01778 AFIX 137 H10A 2 0.735991 1.205901 0.799236 11.00000 -1.50000 H10B 2 0.730433 1.106729 0.921921 11.00000 -1.50000 H10C 2 0.685404 1.216332 0.910431 11.00000 -1.50000 AFIX 0 SADI_BF B1 F1 B1 F2 B1 F3 B1 F4 SADI_BF 0.03 F1 F2 F1 F3 F1 F4 F2 F3 F2 F4 F3 F4 SIMU_BF 0.008 F1 > F4 RIGU_BF F1 > F4 B1 3 0.500000 0.241011 0.750000 10.50000 0.05612 0.06342 = 0.03654 0.00000 -0.00059 0.00000 RESI BF 1 PART -1 20.5 F1 4 0.556152 0.262261 0.703191 20.50000 0.07114 0.07833 = 0.13409 0.04385 0.00931 -0.03062 F2 4 0.479108 0.161580 0.636024 20.50000 0.10009 0.07169 = 0.04012 0.01218 -0.03756 -0.05071 F3 4 0.506759 0.153373 0.859647 20.50000 0.09638 0.05823 = 0.03235 0.00057 0.02454 -0.02575 F4 4 0.471250 0.326825 0.772955 20.50000 0.16406 0.04938 = 0.18646 -0.00229 0.02792 0.07319 RESI BF 2 PART -2 -20.5 F1 4 0.556574 0.262609 0.799585 -20.50000 0.06370 0.11724 = 0.04098 -0.00603 -0.01001 0.01881 F2 4 0.488270 0.370011 0.695543 -20.50000 0.12988 0.03580 = 0.05861 0.00403 -0.01792 0.01620 F3 4 0.498424 0.172150 0.646361 -20.50000 0.08864 0.05750 = 0.04017 -0.01015 -0.04215 -0.00417 F4 4 0.466042 0.229381 0.856560 -20.50000 0.09542 0.14156 = 0.02327 -0.00686 0.01598 -0.05696 PART 0 HKLF 4 REM 5209_a.res in Pcca REM wR2 = 0.147589, GooF = S = 1.21917, Restrained GooF = 1.20297 for all data REM R1 = 0.067856 for 1757 Fo > 4sig(Fo) and 0.090729 for all 2289 data REM 176 parameters refined using 66 restraints END WGHT 0.0201 3.2135 REM Highest difference peak 0.192, deepest hole -0.349, 1-sigma level 0.046 Q1 1 0.4620 0.6595 0.7825 11.00000 0.05 0.19 Q2 1 0.5461 0.8463 0.9226 11.00000 0.05 0.19 Q3 1 0.6089 0.5141 0.4774 11.00000 0.05 0.19 Q4 1 0.6157 0.9995 0.5807 11.00000 0.05 0.19 Q5 1 0.6608 1.0143 0.5781 11.00000 0.05 0.18 ; _shelx_res_checksum 67553 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_sh5217_a _database_code_depnum_ccdc_archive 'CCDC 2260788' loop_ _audit_author_name _audit_author_address 'Bernd Morgenstern' ;Universitaet des Saarlandes Germany ; _audit_update_record ; 2023-05-05 deposited with the CCDC. 2023-09-08 downloaded from the CCDC. ; _audit_creation_method SHELXL-2018/3 _shelx_SHELXL_version_number 2018/3 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H44 P, Br' _chemical_formula_sum 'C20 H44 Br P' _chemical_formula_weight 395.43 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' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _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. ; 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' _cell_length_a 11.605(2) _cell_length_b 14.647(3) _cell_length_c 13.946(3) _cell_angle_alpha 90 _cell_angle_beta 91.312(6) _cell_angle_gamma 90 _cell_volume 2369.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 143(2) _cell_measurement_reflns_used 3265 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 26.75 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.108 _exptl_crystal_F_000 856 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_min 0.060 _exptl_absorpt_coefficient_mu 1.800 _shelx_estimated_absorpt_T_min 0.704 _shelx_estimated_absorpt_T_max 0.900 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4829 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_process_details ; SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., J. Appl. Cryst. 48 (2015) 3-10 ; _exptl_absorpt_special_details ? _diffrn_ambient_temperature 143(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'INCOATEC I\^A?S microfocus sealed tube' _diffrn_measurement_device_type 'Bruker AXS D8 Venture, Photon II' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20644 _diffrn_reflns_av_unetI/netI 0.0594 _diffrn_reflns_av_R_equivalents 0.0815 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.017 _diffrn_reflns_theta_max 25.027 _diffrn_reflns_theta_full 25.027 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measured_fraction_theta_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_point_group_measured_fraction_full 0.993 _reflns_number_total 4158 _reflns_number_gt 2536 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'APEX 4 (Bruker, 2021)' _computing_cell_refinement 'SAINT (Bruker, 2019)' _computing_data_reduction 'SAINT (Bruker, 2019)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _computing_structure_refinement ; SHELXL-2018/3 (Sheldrick, 2018), SHELXLe Rev 1000 (Huebschle et al., 2011) ; _computing_molecular_graphics 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_publication_material 'CIFTAB-2014 (Sheldrick, G. M.)' _refine_special_details ? _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0863P)^2^+1.9766P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 4158 _refine_ls_number_parameters 310 _refine_ls_number_restraints 424 _refine_ls_R_factor_all 0.1077 _refine_ls_R_factor_gt 0.0598 _refine_ls_wR_factor_ref 0.1779 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 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 Br1 Br 0.52303(6) 0.68072(4) 0.60462(4) 0.0810(3) Uani 1 1 d . . . . . P1 P 0.43029(11) 0.38990(9) 0.67437(8) 0.0474(3) Uani 1 1 d . . . . . C1 C 0.3495(4) 0.4662(3) 0.5974(3) 0.0508(12) Uani 1 1 d . . . . . H1A H 0.394995 0.522795 0.589304 0.061 Uiso 1 1 calc R U . . . H1B H 0.340352 0.437436 0.533455 0.061 Uiso 1 1 calc R U . . . C2 C 0.2303(4) 0.4923(3) 0.6327(3) 0.0523(12) Uani 1 1 d . . . . . H2A H 0.182956 0.436348 0.637793 0.063 Uiso 1 1 calc R U . . . H2B H 0.238504 0.519222 0.697550 0.063 Uiso 1 1 calc R U . . . C3 C 0.1682(4) 0.5598(3) 0.5670(4) 0.0562(13) Uani 1 1 d . . . . . H3A H 0.215182 0.615929 0.562138 0.067 Uiso 1 1 calc R U . . . H3B H 0.160090 0.533008 0.502031 0.067 Uiso 1 1 calc R U . . . C4 C 0.0503(4) 0.5844(4) 0.6028(4) 0.0631(14) Uani 1 1 d . . . . . H4A H 0.058915 0.609344 0.668517 0.076 Uiso 1 1 calc R U . . . H4B H 0.003485 0.528052 0.606511 0.076 Uiso 1 1 calc R U . . . C5 C -0.0142(5) 0.6534(4) 0.5406(4) 0.0791(18) Uani 1 1 d . . . . . H5A H -0.089528 0.665924 0.568155 0.119 Uiso 1 1 calc R U . . . H5B H 0.030361 0.710131 0.537809 0.119 Uiso 1 1 calc R U . . . H5C H -0.025148 0.628725 0.475716 0.119 Uiso 1 1 calc R U . . . C6 C 0.5797(4) 0.4074(4) 0.6532(3) 0.0524(12) Uani 1 1 d D . . . . H6A H 0.598457 0.381805 0.589697 0.063 Uiso 0.34(3) 1 calc R U P A 1 H6B H 0.595646 0.473806 0.651516 0.063 Uiso 0.34(3) 1 calc R U P A 1 H6C H 0.594193 0.396047 0.584498 0.063 Uiso 0.66(3) 1 calc R U P A 2 H6D H 0.599113 0.472023 0.666809 0.063 Uiso 0.66(3) 1 calc R U P A 2 C7 C 0.660(2) 0.361(3) 0.733(3) 0.064(4) Uani 0.34(3) 1 d D U P A 1 H7A H 0.637074 0.296852 0.742750 0.077 Uiso 0.34(3) 1 calc R U P A 1 H7B H 0.653506 0.394086 0.794679 0.077 Uiso 0.34(3) 1 calc R U P A 1 C8 C 0.789(2) 0.366(4) 0.697(3) 0.066(3) Uani 0.34(3) 1 d D U P A 1 H8A H 0.809396 0.429695 0.679760 0.079 Uiso 0.34(3) 1 calc R U P A 1 H8B H 0.798480 0.326832 0.639787 0.079 Uiso 0.34(3) 1 calc R U P A 1 C9 C 0.866(2) 0.331(2) 0.785(2) 0.069(4) Uani 0.34(3) 1 d D U P A 1 H9A H 0.870095 0.376952 0.836509 0.083 Uiso 0.34(3) 1 calc R U P A 1 H9B H 0.834648 0.273290 0.810876 0.083 Uiso 0.34(3) 1 calc R U P A 1 C10 C 0.989(2) 0.314(2) 0.741(2) 0.078(5) Uani 0.34(3) 1 d D U P A 1 H10A H 1.042475 0.292261 0.791007 0.117 Uiso 0.34(3) 1 calc R U P A 1 H10B H 0.982898 0.269028 0.689292 0.117 Uiso 0.34(3) 1 calc R U P A 1 H10C H 1.018107 0.371996 0.714753 0.117 Uiso 0.34(3) 1 calc R U P A 1 C7B C 0.6587(11) 0.3465(14) 0.7135(14) 0.064(3) Uani 0.66(3) 1 d . U P A 2 H7C H 0.632046 0.346805 0.780459 0.076 Uiso 0.66(3) 1 calc R U P A 2 H7D H 0.652222 0.283090 0.689327 0.076 Uiso 0.66(3) 1 calc R U P A 2 C8B C 0.7829(12) 0.3745(19) 0.7134(14) 0.065(3) Uani 0.66(3) 1 d . U P A 2 H8C H 0.791243 0.433406 0.747539 0.078 Uiso 0.66(3) 1 calc R U P A 2 H8D H 0.805869 0.384306 0.646205 0.078 Uiso 0.66(3) 1 calc R U P A 2 C9B C 0.8640(10) 0.3061(11) 0.7594(11) 0.066(3) Uani 0.66(3) 1 d . U P A 2 H9C H 0.870532 0.251849 0.717513 0.079 Uiso 0.66(3) 1 calc R U P A 2 H9D H 0.833179 0.285921 0.821579 0.079 Uiso 0.66(3) 1 calc R U P A 2 C10B C 0.9883(10) 0.3512(12) 0.7763(12) 0.078(4) Uani 0.66(3) 1 d . U P A 2 H10D H 1.040568 0.306497 0.806210 0.118 Uiso 0.66(3) 1 calc R U P A 2 H10E H 1.018871 0.370455 0.714528 0.118 Uiso 0.66(3) 1 calc R U P A 2 H10F H 0.981598 0.404454 0.818372 0.118 Uiso 0.66(3) 1 calc R U P A 2 C11 C 0.4015(4) 0.4173(3) 0.7975(3) 0.0532(12) Uani 1 1 d D . . . . H11A H 0.317140 0.419287 0.806311 0.064 Uiso 0.721(8) 1 calc R U P B 1 H11B H 0.433761 0.368865 0.839660 0.064 Uiso 0.721(8) 1 calc R U P B 1 H11C H 0.320264 0.400797 0.808962 0.064 Uiso 0.279(8) 1 calc R U P B 2 H11D H 0.449993 0.376659 0.838241 0.064 Uiso 0.279(8) 1 calc R U P B 2 C12 C 0.4551(9) 0.5112(9) 0.8272(9) 0.068(2) Uani 0.721(8) 1 d D U P B 1 H12A H 0.539021 0.502832 0.838258 0.082 Uiso 0.721(8) 1 calc R U P B 1 H12B H 0.444626 0.554257 0.773004 0.082 Uiso 0.721(8) 1 calc R U P B 1 C13 C 0.4051(8) 0.5541(6) 0.9161(6) 0.074(2) Uani 0.721(8) 1 d D U P B 1 H13A H 0.402235 0.507591 0.967476 0.089 Uiso 0.721(8) 1 calc R U P B 1 H13B H 0.456613 0.603886 0.938706 0.089 Uiso 0.721(8) 1 calc R U P B 1 C14 C 0.2861(8) 0.5919(7) 0.8983(7) 0.093(2) Uani 0.721(8) 1 d D U P B 1 H14A H 0.285815 0.628838 0.838810 0.111 Uiso 0.721(8) 1 calc R U P B 1 H14B H 0.231638 0.540597 0.888133 0.111 Uiso 0.721(8) 1 calc R U P B 1 C15 C 0.2457(11) 0.6493(10) 0.9783(9) 0.121(4) Uani 0.721(8) 1 d D U P B 1 H15A H 0.167981 0.671995 0.962886 0.182 Uiso 0.721(8) 1 calc R U P B 1 H15B H 0.244003 0.612750 1.037111 0.182 Uiso 0.721(8) 1 calc R U P B 1 H15C H 0.298205 0.701030 0.987766 0.182 Uiso 0.721(8) 1 calc R U P B 1 C12B C 0.418(3) 0.506(3) 0.831(3) 0.074(4) Uani 0.279(8) 1 d D U P B 2 H12C H 0.401037 0.549105 0.777812 0.089 Uiso 0.279(8) 1 calc R U P B 2 H12D H 0.499740 0.513655 0.850602 0.089 Uiso 0.279(8) 1 calc R U P B 2 C13B C 0.342(2) 0.5290(14) 0.9153(17) 0.080(3) Uani 0.279(8) 1 d D U P B 2 H13C H 0.259738 0.523230 0.895826 0.096 Uiso 0.279(8) 1 calc R U P B 2 H13D H 0.357875 0.486081 0.968767 0.096 Uiso 0.279(8) 1 calc R U P B 2 C14B C 0.367(2) 0.6262(14) 0.9477(16) 0.088(3) Uani 0.279(8) 1 d D U P B 2 H14C H 0.445525 0.628324 0.977235 0.106 Uiso 0.279(8) 1 calc R U P B 2 H14D H 0.366701 0.666494 0.890714 0.106 Uiso 0.279(8) 1 calc R U P B 2 C15B C 0.283(2) 0.663(2) 1.018(2) 0.106(6) Uani 0.279(8) 1 d D U P B 2 H15D H 0.304473 0.725353 1.035857 0.159 Uiso 0.279(8) 1 calc R U P B 2 H15E H 0.205378 0.662505 0.989082 0.159 Uiso 0.279(8) 1 calc R U P B 2 H15F H 0.284300 0.624287 1.075710 0.159 Uiso 0.279(8) 1 calc R U P B 2 C16 C 0.3961(4) 0.2719(4) 0.6505(4) 0.0577(13) Uani 1 1 d D . . . . H16A H 0.412899 0.258063 0.582780 0.069 Uiso 0.477(11) 1 calc R U P C 1 H16B H 0.446269 0.232727 0.691489 0.069 Uiso 0.477(11) 1 calc R U P C 1 H16C H 0.428169 0.255883 0.587540 0.069 Uiso 0.523(11) 1 calc R U P C 2 H16D H 0.437077 0.234343 0.699443 0.069 Uiso 0.523(11) 1 calc R U P C 2 C17 C 0.2692(19) 0.2486(18) 0.669(3) 0.102(4) Uani 0.477(11) 1 d D U P C 1 H17A H 0.218459 0.280569 0.622040 0.123 Uiso 0.477(11) 1 calc R U P C 1 H17B H 0.248631 0.269097 0.734263 0.123 Uiso 0.477(11) 1 calc R U P C 1 C18 C 0.2521(14) 0.1447(15) 0.6603(18) 0.116(4) Uani 0.477(11) 1 d D U P C 1 H18A H 0.294390 0.121421 0.604501 0.139 Uiso 0.477(11) 1 calc R U P C 1 H18B H 0.282987 0.114039 0.718674 0.139 Uiso 0.477(11) 1 calc R U P C 1 C19 C 0.1275(14) 0.1244(13) 0.6479(17) 0.131(4) Uani 0.477(11) 1 d D U P C 1 H19A H 0.091075 0.181988 0.625655 0.157 Uiso 0.477(11) 1 calc R U P C 1 H19B H 0.098800 0.113138 0.713125 0.157 Uiso 0.477(11) 1 calc R U P C 1 C20 C 0.0753(18) 0.0490(13) 0.5845(17) 0.153(6) Uani 0.477(11) 1 d D U P C 1 H20A H -0.008817 0.050052 0.588954 0.229 Uiso 0.477(11) 1 calc R U P C 1 H20B H 0.096796 0.059116 0.517769 0.229 Uiso 0.477(11) 1 calc R U P C 1 H20C H 0.104603 -0.010458 0.606158 0.229 Uiso 0.477(11) 1 calc R U P C 1 C17B C 0.2713(19) 0.2443(18) 0.649(3) 0.104(4) Uani 0.523(11) 1 d D U P C 2 H17C H 0.225817 0.289321 0.611284 0.125 Uiso 0.523(11) 1 calc R U P C 2 H17D H 0.242756 0.244797 0.715487 0.125 Uiso 0.523(11) 1 calc R U P C 2 C18B C 0.2525(14) 0.1466(15) 0.6047(15) 0.119(4) Uani 0.523(11) 1 d D U P C 2 H18C H 0.323654 0.131136 0.570408 0.142 Uiso 0.523(11) 1 calc R U P C 2 H18D H 0.247699 0.103444 0.659115 0.142 Uiso 0.523(11) 1 calc R U P C 2 C19B C 0.1536(13) 0.1255(13) 0.5380(13) 0.140(4) Uani 0.523(11) 1 d D U P C 2 H19C H 0.160641 0.065492 0.506056 0.167 Uiso 0.523(11) 1 calc R U P C 2 H19D H 0.138246 0.174216 0.490228 0.167 Uiso 0.523(11) 1 calc R U P C 2 C20B C 0.0685(15) 0.1252(16) 0.6195(15) 0.150(5) Uani 0.523(11) 1 d D U P C 2 H20D H -0.009000 0.112050 0.593791 0.224 Uiso 0.523(11) 1 calc R U P C 2 H20E H 0.090908 0.078198 0.666377 0.224 Uiso 0.523(11) 1 calc R U P C 2 H20F H 0.068891 0.185087 0.650815 0.224 Uiso 0.523(11) 1 calc R U P C 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 Br1 0.1400(7) 0.0589(4) 0.0442(3) -0.0126(3) 0.0059(3) -0.0222(4) P1 0.0558(7) 0.0507(8) 0.0356(6) 0.0033(5) -0.0020(5) 0.0011(6) C1 0.062(3) 0.052(3) 0.039(3) 0.004(2) -0.008(2) -0.005(2) C2 0.059(3) 0.054(3) 0.044(3) 0.006(2) -0.011(2) 0.006(2) C3 0.066(3) 0.050(3) 0.052(3) 0.004(2) -0.016(2) -0.001(2) C4 0.065(3) 0.063(3) 0.061(3) -0.007(3) -0.014(3) 0.006(3) C5 0.085(4) 0.072(4) 0.079(4) 0.000(3) -0.025(3) 0.017(3) C6 0.059(3) 0.058(3) 0.040(3) 0.005(2) -0.005(2) 0.001(2) C7 0.054(5) 0.085(8) 0.053(9) 0.026(7) 0.000(5) 0.009(5) C8 0.054(4) 0.087(7) 0.056(7) 0.022(6) 0.001(4) 0.007(4) C9 0.055(5) 0.091(8) 0.061(8) 0.020(6) -0.002(5) 0.012(5) C10 0.062(7) 0.100(12) 0.071(11) 0.017(9) -0.002(7) 0.023(8) C7B 0.054(3) 0.083(7) 0.054(8) 0.019(5) 0.000(4) 0.006(4) C8B 0.054(3) 0.087(6) 0.055(7) 0.022(5) 0.003(3) 0.007(3) C9B 0.054(3) 0.091(7) 0.052(6) 0.013(5) 0.005(4) 0.009(4) C10B 0.059(5) 0.103(9) 0.072(8) 0.005(6) -0.005(5) 0.015(5) C11 0.063(3) 0.061(3) 0.036(3) 0.011(2) 0.003(2) 0.011(2) C12 0.099(6) 0.065(4) 0.040(3) -0.005(3) -0.008(4) -0.003(5) C13 0.103(5) 0.071(4) 0.049(3) -0.011(3) -0.005(4) 0.000(4) C14 0.114(5) 0.093(5) 0.071(4) -0.020(4) -0.010(4) 0.011(4) C15 0.138(8) 0.118(7) 0.107(8) -0.047(6) -0.015(6) 0.040(7) C12B 0.104(8) 0.072(6) 0.045(5) -0.007(5) -0.012(6) 0.009(6) C13B 0.105(7) 0.080(5) 0.055(5) -0.012(5) -0.011(5) 0.009(5) C14B 0.110(7) 0.086(6) 0.067(6) -0.021(5) -0.011(6) 0.008(6) C15B 0.118(11) 0.113(10) 0.086(11) -0.038(9) -0.011(9) 0.016(10) C16 0.063(3) 0.053(3) 0.057(3) 0.000(3) -0.002(2) -0.001(2) C17 0.073(5) 0.057(5) 0.176(12) 0.004(7) -0.020(6) -0.014(5) C18 0.088(5) 0.069(5) 0.190(11) 0.006(7) -0.012(6) -0.023(4) C19 0.101(6) 0.093(6) 0.199(10) -0.008(7) -0.015(7) -0.029(6) C20 0.128(10) 0.110(10) 0.220(13) -0.025(10) -0.019(10) -0.026(9) C17B 0.074(5) 0.060(5) 0.178(12) 0.010(6) -0.021(6) -0.008(5) C18B 0.089(5) 0.082(5) 0.184(11) 0.004(7) -0.020(6) -0.021(4) C19B 0.116(7) 0.100(6) 0.201(11) -0.018(8) -0.023(6) -0.015(6) C20B 0.115(9) 0.108(9) 0.225(13) -0.010(10) -0.013(9) -0.021(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C6 1.784(5) . ? P1 C1 1.798(5) . ? P1 C11 1.802(5) . ? P1 C16 1.802(5) . ? C1 C2 1.527(7) . ? C2 C3 1.518(6) . ? C3 C4 1.511(7) . ? C4 C5 1.518(7) . ? C6 C7B 1.520(17) . ? C6 C7 1.59(3) . ? C7 C8 1.59(3) . ? C8 C9 1.59(3) . ? C9 C10 1.59(3) . ? C7B C8B 1.50(2) . ? C8B C9B 1.51(2) . ? C9B C10B 1.60(2) . ? C11 C12B 1.39(3) . ? C11 C12 1.561(11) . ? C12 C13 1.517(9) . ? C13 C14 1.503(10) . ? C14 C15 1.482(10) . ? C12B C13B 1.526(15) . ? C13B C14B 1.520(15) . ? C14B C15B 1.500(15) . ? C16 C17B 1.50(2) . ? C16 C17 1.540(16) . ? C17 C18 1.540(14) . ? C18 C19 1.483(14) . ? C19 C20 1.531(14) . ? C17B C18B 1.572(13) . ? C18B C19B 1.493(13) . ? C19B C20B 1.522(14) . ? 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 C6 P1 C1 107.9(2) . . ? C6 P1 C11 109.1(2) . . ? C1 P1 C11 108.9(2) . . ? C6 P1 C16 108.5(2) . . ? C1 P1 C16 112.1(2) . . ? C11 P1 C16 110.2(2) . . ? C2 C1 P1 115.2(3) . . ? C3 C2 C1 112.9(4) . . ? C4 C3 C2 112.2(4) . . ? C3 C4 C5 114.2(5) . . ? C7B C6 P1 113.6(7) . . ? C7 C6 P1 112.3(13) . . ? C6 C7 C8 107(3) . . ? C7 C8 C9 105(4) . . ? C10 C9 C8 104(3) . . ? C8B C7B C6 114.0(19) . . ? C7B C8B C9B 114(2) . . ? C8B C9B C10B 109.8(17) . . ? C12B C11 P1 120.0(16) . . ? C12 C11 P1 111.6(5) . . ? C13 C12 C11 115.1(8) . . ? C14 C13 C12 112.6(7) . . ? C15 C14 C13 113.0(8) . . ? C11 C12B C13B 113(2) . . ? C14B C13B C12B 109.2(19) . . ? C15B C14B C13B 114(2) . . ? C17B C16 P1 118.0(10) . . ? C17 C16 P1 112.9(10) . . ? C16 C17 C18 109.1(16) . . ? C19 C18 C17 109.4(16) . . ? C18 C19 C20 125.7(18) . . ? C16 C17B C18B 112.0(15) . . ? C19B C18B C17B 122.1(17) . . ? C18B C19B C20B 92.2(15) . . ? _refine_diff_density_max 0.652 _refine_diff_density_min -0.583 _refine_diff_density_rms 0.068 _shelx_res_file ; TITL sh5217_a.res in P2(1)/c sh5217_a.res created by SHELXL-2018/3 at 15:00:40 on 20-Mar-2023 REM Old TITL sh5217 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.306, Rweak 0.041, Alpha 0.051 REM 0.417 for 188 systematic absences, Orientation as input REM Formula found by SHELXT: C19 P Br CELL 0.71073 11.6049 14.6473 13.9459 90.000 91.312 90.000 ZERR 4.000 0.0023 0.0028 0.0026 0.000 0.006 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H P BR UNIT 80 176 4 4 TEMP -130.150 SIZE 0.06 0.16 0.21 L.S. 32 SHEL 10000 0.84 BOND ACTA LIST 4 FMAP 2 PLAN -5 WGHT 0.086300 1.976600 FVAR 0.42049 0.72118 0.47679 0.33779 BR1 4 0.523030 0.680718 0.604615 11.00000 0.14005 0.05888 = 0.04416 -0.01258 0.00590 -0.02218 P1 3 0.430290 0.389897 0.674366 11.00000 0.05579 0.05068 = 0.03556 0.00329 -0.00197 0.00111 C1 1 0.349545 0.466231 0.597397 11.00000 0.06170 0.05151 = 0.03884 0.00432 -0.00809 -0.00502 AFIX 23 H1A 2 0.394995 0.522795 0.589304 11.00000 -1.20000 H1B 2 0.340352 0.437436 0.533455 11.00000 -1.20000 AFIX 0 C2 1 0.230344 0.492262 0.632653 11.00000 0.05866 0.05393 = 0.04362 0.00603 -0.01131 0.00591 AFIX 23 H2A 2 0.182956 0.436348 0.637793 11.00000 -1.20000 H2B 2 0.238504 0.519222 0.697550 11.00000 -1.20000 AFIX 0 C3 1 0.168237 0.559757 0.567026 11.00000 0.06641 0.04957 = 0.05177 0.00433 -0.01590 -0.00100 AFIX 23 H3A 2 0.215182 0.615929 0.562138 11.00000 -1.20000 H3B 2 0.160090 0.533008 0.502031 11.00000 -1.20000 AFIX 0 C4 1 0.050314 0.584381 0.602772 11.00000 0.06495 0.06277 = 0.06093 -0.00679 -0.01392 0.00621 AFIX 23 H4A 2 0.058915 0.609344 0.668517 11.00000 -1.20000 H4B 2 0.003485 0.528052 0.606511 11.00000 -1.20000 AFIX 0 C5 1 -0.014220 0.653408 0.540603 11.00000 0.08489 0.07217 = 0.07893 -0.00011 -0.02525 0.01720 AFIX 33 H5A 2 -0.089528 0.665924 0.568155 11.00000 -1.50000 H5B 2 0.030361 0.710131 0.537809 11.00000 -1.50000 H5C 2 -0.025148 0.628725 0.475716 11.00000 -1.50000 AFIX 0 C6 1 0.579716 0.407430 0.653152 11.00000 0.05885 0.05776 = 0.04017 0.00479 -0.00534 0.00099 PART 1 AFIX 23 H6A 2 0.598457 0.381805 0.589697 41.00000 -1.20000 H6B 2 0.595646 0.473806 0.651516 41.00000 -1.20000 AFIX 23 PART 2 H6C 2 0.594193 0.396047 0.584498 -41.00000 -1.20000 H6D 2 0.599113 0.472023 0.666809 -41.00000 -1.20000 AFIX 0 PART 0 SADI C6 C7 C7 C8 C8 C9 C9 C10 SiMU 0.01 C7 > C10 C7b > C10b RIGU C7 > C10 C7b > C10b PART 1 41 C7 1 0.660086 0.361213 0.733020 41.00000 0.05392 0.08481 = 0.05281 0.02575 -0.00024 0.00851 AFIX 23 H7A 2 0.637074 0.296852 0.742750 41.00000 -1.20000 H7B 2 0.653506 0.394086 0.794679 41.00000 -1.20000 AFIX 0 C8 1 0.788665 0.366241 0.696692 41.00000 0.05395 0.08701 = 0.05625 0.02156 0.00126 0.00702 AFIX 23 H8A 2 0.809396 0.429695 0.679760 41.00000 -1.20000 H8B 2 0.798480 0.326832 0.639787 41.00000 -1.20000 AFIX 0 C9 1 0.865999 0.330759 0.784720 41.00000 0.05506 0.09117 = 0.06057 0.01977 -0.00160 0.01197 AFIX 23 H9A 2 0.870095 0.376952 0.836509 41.00000 -1.20000 H9B 2 0.834648 0.273290 0.810876 41.00000 -1.20000 AFIX 0 C10 1 0.989131 0.314453 0.740743 41.00000 0.06196 0.10023 = 0.07090 0.01729 -0.00153 0.02272 AFIX 33 H10A 2 1.042475 0.292261 0.791007 41.00000 -1.50000 H10B 2 0.982898 0.269028 0.689292 41.00000 -1.50000 H10C 2 1.018107 0.371996 0.714753 41.00000 -1.50000 AFIX 0 PART 2 -41 C7B 1 0.658712 0.346462 0.713535 -41.00000 0.05373 0.08289 = 0.05448 0.01894 -0.00017 0.00565 AFIX 23 H7C 2 0.632046 0.346805 0.780459 -41.00000 -1.20000 H7D 2 0.652222 0.283090 0.689327 -41.00000 -1.20000 AFIX 0 C8B 1 0.782912 0.374457 0.713352 -41.00000 0.05355 0.08662 = 0.05537 0.02201 0.00303 0.00699 AFIX 23 H8C 2 0.791243 0.433406 0.747539 -41.00000 -1.20000 H8D 2 0.805869 0.384306 0.646205 -41.00000 -1.20000 AFIX 0 C9B 1 0.863960 0.306063 0.759427 -41.00000 0.05378 0.09116 = 0.05191 0.01349 0.00542 0.00947 AFIX 23 H9C 2 0.870532 0.251849 0.717513 -41.00000 -1.20000 H9D 2 0.833179 0.285921 0.821579 -41.00000 -1.20000 AFIX 0 C10B 1 0.988291 0.351243 0.776265 -41.00000 0.05924 0.10323 = 0.07232 0.00536 -0.00505 0.01499 AFIX 33 H10D 2 1.040568 0.306497 0.806210 -41.00000 -1.50000 H10E 2 1.018871 0.370455 0.714528 -41.00000 -1.50000 H10F 2 0.981598 0.404454 0.818372 -41.00000 -1.50000 AFIX 0 PART 0 C11 1 0.401506 0.417327 0.797470 11.00000 0.06293 0.06065 = 0.03624 0.01114 0.00331 0.01113 PART 1 AFIX 23 H11A 2 0.317140 0.419287 0.806311 21.00000 -1.20000 H11B 2 0.433761 0.368865 0.839660 21.00000 -1.20000 AFIX 23 PART 2 H11C 2 0.320264 0.400797 0.808962 -21.00000 -1.20000 H11D 2 0.449993 0.376659 0.838241 -21.00000 -1.20000 AFIX 0 PART 0 SADI C11 C12 C12 C13 C13 C14 C14 C15 SIMU 0.01 C12 > C15 C12b > C15b RIGU C12 > C15 C12b > C15b PART 1 21 C12 1 0.455109 0.511179 0.827206 21.00000 0.09920 0.06543 = 0.03967 -0.00503 -0.00779 -0.00267 AFIX 23 H12A 2 0.539021 0.502832 0.838258 21.00000 -1.20000 H12B 2 0.444626 0.554257 0.773004 21.00000 -1.20000 AFIX 0 C13 1 0.405132 0.554085 0.916063 21.00000 0.10251 0.07090 = 0.04940 -0.01118 -0.00538 0.00025 AFIX 23 H13A 2 0.402235 0.507591 0.967476 21.00000 -1.20000 H13B 2 0.456613 0.603886 0.938706 21.00000 -1.20000 AFIX 0 C14 1 0.286125 0.591888 0.898257 21.00000 0.11353 0.09316 = 0.07131 -0.02000 -0.01013 0.01082 AFIX 23 H14A 2 0.285815 0.628838 0.838810 21.00000 -1.20000 H14B 2 0.231638 0.540597 0.888133 21.00000 -1.20000 AFIX 0 C15 1 0.245650 0.649277 0.978283 21.00000 0.13810 0.11761 = 0.10692 -0.04717 -0.01550 0.04043 AFIX 33 H15A 2 0.167981 0.671995 0.962886 21.00000 -1.50000 H15B 2 0.244003 0.612750 1.037111 21.00000 -1.50000 H15C 2 0.298205 0.701030 0.987766 21.00000 -1.50000 AFIX 0 SAME C11 > C15 PART 2 -21 C12B 1 0.417883 0.505773 0.830780 -21.00000 0.10358 0.07246 = 0.04537 -0.00729 -0.01240 0.00931 AFIX 23 H12C 2 0.401037 0.549105 0.777812 -21.00000 -1.20000 H12D 2 0.499740 0.513655 0.850602 -21.00000 -1.20000 AFIX 0 C13B 1 0.341996 0.529027 0.915264 -21.00000 0.10534 0.07983 = 0.05480 -0.01241 -0.01118 0.00949 AFIX 23 H13C 2 0.259738 0.523230 0.895826 -21.00000 -1.20000 H13D 2 0.357875 0.486081 0.968767 -21.00000 -1.20000 AFIX 0 C14B 1 0.367171 0.626201 0.947716 -21.00000 0.10976 0.08625 = 0.06740 -0.02127 -0.01081 0.00805 AFIX 23 H14C 2 0.445525 0.628324 0.977235 -21.00000 -1.20000 H14D 2 0.366701 0.666494 0.890714 -21.00000 -1.20000 AFIX 0 C15B 1 0.283039 0.662755 1.018200 -21.00000 0.11844 0.11322 = 0.08602 -0.03806 -0.01099 0.01637 AFIX 33 H15D 2 0.304473 0.725353 1.035857 -21.00000 -1.50000 H15E 2 0.205378 0.662505 0.989082 -21.00000 -1.50000 H15F 2 0.284300 0.624287 1.075710 -21.00000 -1.50000 AFIX 0 PART 0 C16 1 0.396110 0.271946 0.650517 11.00000 0.06275 0.05334 = 0.05695 -0.00004 -0.00163 -0.00098 PART 1 AFIX 23 H16A 2 0.412899 0.258063 0.582780 31.00000 -1.20000 H16B 2 0.446269 0.232727 0.691489 31.00000 -1.20000 AFIX 23 PART 2 H16C 2 0.428169 0.255883 0.587540 -31.00000 -1.20000 H16D 2 0.437077 0.234343 0.699443 -31.00000 -1.20000 AFIX 0 PART 0 SADI C16 C17 C17 C18 C18 C19 C19 C20 SIMU 0.01 C17 > C20 C17b > C20b RIGU C17 > C20 C17b > C20b PaRT 1 31 C17 1 0.269204 0.248648 0.669193 31.00000 0.07286 0.05661 = 0.17631 0.00414 -0.01998 -0.01422 AFIX 23 H17A 2 0.218459 0.280569 0.622040 31.00000 -1.20000 H17B 2 0.248631 0.269097 0.734263 31.00000 -1.20000 AFIX 0 C18 1 0.252095 0.144718 0.660287 31.00000 0.08792 0.06886 = 0.18957 0.00576 -0.01163 -0.02288 AFIX 23 H18A 2 0.294390 0.121421 0.604501 31.00000 -1.20000 H18B 2 0.282987 0.114039 0.718674 31.00000 -1.20000 AFIX 0 C19 1 0.127490 0.124399 0.647870 31.00000 0.10060 0.09262 = 0.19917 -0.00777 -0.01519 -0.02944 AFIX 23 H19A 2 0.091075 0.181988 0.625655 31.00000 -1.20000 H19B 2 0.098800 0.113138 0.713125 31.00000 -1.20000 AFIX 0 C20 1 0.075326 0.048995 0.584487 31.00000 0.12782 0.10970 = 0.21969 -0.02505 -0.01929 -0.02584 AFIX 33 H20A 2 -0.008817 0.050052 0.588954 31.00000 -1.50000 H20B 2 0.096796 0.059116 0.517769 31.00000 -1.50000 H20C 2 0.104603 -0.010458 0.606158 31.00000 -1.50000 AFIX 0 SAME C16 > C20 PART 2 -31 C17B 1 0.271314 0.244272 0.649139 -31.00000 0.07398 0.06035 = 0.17774 0.01019 -0.02125 -0.00801 AFIX 23 H17C 2 0.225817 0.289321 0.611284 -31.00000 -1.20000 H17D 2 0.242756 0.244797 0.715487 -31.00000 -1.20000 AFIX 0 C18B 1 0.252514 0.146609 0.604727 -31.00000 0.08909 0.08181 = 0.18430 0.00388 -0.01969 -0.02117 AFIX 23 H18C 2 0.323654 0.131136 0.570408 -31.00000 -1.20000 H18D 2 0.247699 0.103444 0.659115 -31.00000 -1.20000 AFIX 0 C19B 1 0.153643 0.125511 0.538045 -31.00000 0.11591 0.09991 = 0.20148 -0.01846 -0.02309 -0.01493 AFIX 23 H19C 2 0.160641 0.065492 0.506056 -31.00000 -1.20000 H19D 2 0.138246 0.174216 0.490228 -31.00000 -1.20000 AFIX 0 C20B 1 0.068529 0.125182 0.619514 -31.00000 0.11540 0.10784 = 0.22494 -0.00968 -0.01346 -0.02136 AFIX 33 H20D 2 -0.009000 0.112050 0.593791 -31.00000 -1.50000 H20E 2 0.090908 0.078198 0.666377 -31.00000 -1.50000 H20F 2 0.068891 0.185087 0.650815 -31.00000 -1.50000 PART 0 AFIX 0 HKLF 4 REM sh5217_a.res in P2(1)/c REM wR2 = 0.177949, GooF = S = 1.02756, Restrained GooF = 1.02666 for all data REM R1 = 0.059776 for 2536 Fo > 4sig(Fo) and 0.107674 for all 4158 data REM 310 parameters refined using 424 restraints END WGHT 0.0863 1.9766 REM Highest difference peak 0.652, deepest hole -0.583, 1-sigma level 0.068 Q1 1 0.2496 0.0934 0.5961 11.00000 0.05 0.65 Q2 1 0.6210 0.6801 0.6020 11.00000 0.05 0.50 Q3 1 0.4935 0.7293 0.5668 11.00000 0.05 0.49 Q4 1 0.2244 0.1682 0.6173 11.00000 0.05 0.40 Q5 1 0.2988 0.6816 0.9142 11.00000 0.05 0.35 ; _shelx_res_checksum 25228