#------------------------------------------------------------------------------ #$Date: 2020-07-06 06:31:08 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253953 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/05/96/7059672.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7059672 loop_ _publ_author_name 'Ling, Irene' 'Skelton, Brian W.' 'Sobolev, Alexandre N.' 'Alias, Yatimah' 'Khor, Zong Chin' 'Raston, Colin L.' _publ_section_title ; Effect of anions on the solid-state interplay of symmetric and unsymmetric phosphonium cations ; _journal_issue 25 _journal_name_full 'New Journal of Chemistry' _journal_page_first 10220 _journal_paper_doi 10.1039/D0NJ01975E _journal_volume 44 _journal_year 2020 _chemical_formula_moiety 'C25 H22 P, B F4' _chemical_formula_sum 'C25 H22 B F4 P' _chemical_formula_weight 440.20 _chemical_melting_point 477.6(15) _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2020-02-25 deposited with the CCDC. 2020-05-22 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 107.748(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.5047(2) _cell_length_b 21.5886(5) _cell_length_c 11.1289(3) _cell_measurement_reflns_used 14894 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 32.1858 _cell_measurement_theta_min 2.8248 _cell_volume 2174.89(10) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) ; _computing_molecular_graphics 'X-Seed v. 4.0 (Barbour, 2001)' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 16.0009 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.955 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur-S, Sapphire3 CCD' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_unetI/netI 0.0287 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.955 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 49312 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.955 _diffrn_reflns_theta_full 30.000 _diffrn_reflns_theta_max 32.258 _diffrn_reflns_theta_min 2.937 _exptl_absorpt_coefficient_mu 0.170 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.847 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) (compiled Jan 23 2012,18:06:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.344 _exptl_crystal_description blade _exptl_crystal_F_000 912 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.677 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.070 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 280 _refine_ls_number_reflns 7373 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.003 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0786 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+7.1000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1660 _refine_ls_wR_factor_ref 0.1698 _reflns_Friedel_coverage 0.000 _reflns_number_gt 6785 _reflns_number_total 7373 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0nj01975e1.cif _cod_data_source_block 080528b7 _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value '203-206 C' was changed to '477.6(15)' -- it was converted from degrees Celsius (C) to kelvins (K), the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas Adding full bibliography for 7059666--7059672.cif. ; _cod_original_cell_volume 2174.89(1) _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7059672 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.935 _shelx_estimated_absorpt_t_max 0.970 _shelx_res_file ; TITL 080528b7 in P2(1)/c 080528b7.res created by SHELXL-2018/3 at 13:57:24 on 24-Feb-2020 CELL 0.71073 9.5047 21.5886 11.1289 90.000 107.748 90.000 ZERR 4.00 0.0002 0.0005 0.0003 0.000 0.003 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H B F P UNIT 100 88 4 16 4 ACTA 60 TEMP -173 SIZE 0.40 0.22 0.18 CONF HTAB BOND $H L.S. 10 WGHT 0.030000 7.100000 FVAR 0.36761 P1 5 0.568827 0.139870 0.639787 11.00000 0.01608 0.01826 = 0.01998 -0.00024 0.00955 0.00081 C1 1 0.470812 0.066984 0.601934 11.00000 0.01850 0.01800 = 0.01970 -0.00012 0.00893 0.00004 AFIX 23 H1A 2 0.417167 0.066058 0.510468 11.00000 -1.20000 H1B 2 0.543517 0.032729 0.620192 11.00000 -1.20000 AFIX 0 C11 1 0.666881 0.141328 0.804345 11.00000 0.01816 0.02061 = 0.02195 -0.00317 0.01006 -0.00115 C12 1 0.815412 0.122853 0.843880 11.00000 0.02022 0.02367 = 0.02434 -0.00082 0.01056 0.00003 AFIX 43 H12 2 0.865824 0.115684 0.783438 11.00000 -1.20000 AFIX 0 C13 1 0.888352 0.115093 0.971016 11.00000 0.02002 0.02816 = 0.02463 0.00006 0.00522 -0.00052 AFIX 43 H13 2 0.989074 0.102736 0.997672 11.00000 -1.20000 AFIX 0 C14 1 0.815475 0.125223 1.059811 11.00000 0.03035 0.02712 = 0.02218 -0.00205 0.00783 -0.00494 AFIX 43 H14 2 0.866359 0.119807 1.146973 11.00000 -1.20000 AFIX 0 C15 1 0.667833 0.143320 1.021502 11.00000 0.03109 0.02859 = 0.02594 -0.00411 0.01607 -0.00335 AFIX 43 H15 2 0.618305 0.150358 1.082617 11.00000 -1.20000 AFIX 0 C16 1 0.592879 0.151098 0.894298 11.00000 0.02094 0.02568 = 0.02721 -0.00380 0.01263 -0.00152 AFIX 43 H16 2 0.491840 0.162992 0.868167 11.00000 -1.20000 AFIX 0 C21 1 0.697373 0.146867 0.550964 11.00000 0.01741 0.02023 = 0.01948 0.00152 0.00890 0.00139 C22 1 0.710783 0.101115 0.467110 11.00000 0.02320 0.02478 = 0.02477 -0.00334 0.01323 -0.00234 AFIX 43 H22 2 0.651787 0.064790 0.456056 11.00000 -1.20000 AFIX 0 C23 1 0.811451 0.108791 0.399129 11.00000 0.02750 0.02919 = 0.02499 -0.00343 0.01579 -0.00096 AFIX 43 H23 2 0.820689 0.077743 0.341510 11.00000 -1.20000 AFIX 0 C24 1 0.897859 0.161854 0.415976 11.00000 0.02404 0.03029 = 0.02757 0.00393 0.01541 0.00045 AFIX 43 H24 2 0.966459 0.166879 0.369975 11.00000 -1.20000 AFIX 0 C25 1 0.884754 0.207569 0.499465 11.00000 0.02882 0.02400 = 0.03648 0.00042 0.01971 -0.00444 AFIX 43 H25 2 0.944123 0.243781 0.510407 11.00000 -1.20000 AFIX 0 C26 1 0.784379 0.200347 0.567336 11.00000 0.02696 0.02088 = 0.03393 -0.00329 0.01786 -0.00222 AFIX 43 H26 2 0.775093 0.231623 0.624490 11.00000 -1.20000 AFIX 0 C31 1 0.442574 0.203719 0.594452 11.00000 0.01937 0.01869 = 0.03117 0.00250 0.01470 0.00151 C32 1 0.342602 0.202533 0.472549 11.00000 0.02405 0.02441 = 0.03238 0.00435 0.00991 0.00133 AFIX 43 H32 2 0.336379 0.167046 0.420704 11.00000 -1.20000 AFIX 0 C33 1 0.252164 0.253607 0.427444 11.00000 0.02328 0.03295 = 0.04748 0.01307 0.01234 0.00385 AFIX 43 H33 2 0.183895 0.252994 0.344849 11.00000 -1.20000 AFIX 0 C34 1 0.262200 0.305334 0.503589 11.00000 0.03445 0.03018 = 0.06515 0.01583 0.03092 0.01410 AFIX 43 H34 2 0.201147 0.340256 0.472479 11.00000 -1.20000 AFIX 0 C35 1 0.360044 0.306510 0.624075 11.00000 0.04765 0.02318 = 0.05768 0.00030 0.03440 0.00920 AFIX 43 H35 2 0.364938 0.341993 0.675680 11.00000 -1.20000 AFIX 0 C36 1 0.452019 0.255845 0.670721 11.00000 0.03448 0.02482 = 0.03630 -0.00298 0.02051 0.00142 AFIX 43 H36 2 0.520155 0.256872 0.753354 11.00000 -1.20000 AFIX 0 C41 1 0.361863 0.056171 0.674464 11.00000 0.01792 0.01839 = 0.01870 0.00055 0.00811 -0.00014 C42 1 0.213333 0.071684 0.621288 11.00000 0.01988 0.02777 = 0.02414 0.00434 0.01015 0.00250 AFIX 43 H42 2 0.180598 0.089823 0.539691 11.00000 -1.20000 AFIX 0 C43 1 0.112825 0.060641 0.687557 11.00000 0.01943 0.03306 = 0.03171 0.00234 0.01280 0.00234 AFIX 43 H43 2 0.011490 0.070613 0.650292 11.00000 -1.20000 AFIX 0 C44 1 0.159992 0.035172 0.807606 11.00000 0.02673 0.02803 = 0.02943 -0.00146 0.01774 -0.00384 AFIX 43 H44 2 0.091464 0.028441 0.853084 11.00000 -1.20000 AFIX 0 C45 1 0.307441 0.019547 0.861130 11.00000 0.02762 0.02722 = 0.01827 0.00075 0.00890 -0.00447 AFIX 43 H45 2 0.339869 0.002110 0.943376 11.00000 -1.20000 AFIX 0 C46 1 0.408483 0.029395 0.794339 11.00000 0.01867 0.02548 = 0.02007 0.00065 0.00506 -0.00194 AFIX 43 H46 2 0.508994 0.017852 0.830569 11.00000 -1.20000 AFIX 0 B1 3 0.220705 0.052621 0.251290 11.00000 0.01864 0.02209 = 0.02052 0.00074 0.00485 0.00195 F1 4 0.201962 0.001240 0.318793 11.00000 0.03094 0.03543 = 0.04376 0.01111 0.01418 -0.00216 F2 4 0.370437 0.071288 0.299015 11.00000 0.02027 0.03322 = 0.02748 0.00484 0.00531 -0.00058 F3 4 0.190184 0.038818 0.124509 11.00000 0.04033 0.04915 = 0.02434 -0.00577 0.00454 0.00868 F4 4 0.132823 0.101549 0.267749 11.00000 0.02723 0.03606 = 0.03939 -0.00519 0.00822 0.00819 HKLF 4 REM 080528b7 in P2(1)/c REM wR2 = 0.1698, GooF = S = 1.003, Restrained GooF = 1.003 for all data REM R1 = 0.0786 for 6785 Fo > 4sig(Fo) and 0.0856 for all 7373 data REM 280 parameters refined using 0 restraints END WGHT 0.0255 3.2647 REM Instructions for potential hydrogen bonds HTAB C1 F2 EQIV $1 -x+1, -y, -z+1 HTAB C1 F1_$1 HTAB C1 F2_$1 HTAB C32 F2 HTAB C32 F4 REM Highest difference peak 0.677, deepest hole -0.373, 1-sigma level 0.070 Q1 1 0.5598 0.1006 0.6365 11.00000 0.05 0.68 Q2 1 0.5580 0.1813 0.6426 11.00000 0.05 0.67 Q3 1 0.6323 0.1396 0.7205 11.00000 0.05 0.64 Q4 1 0.7774 0.1639 0.5809 11.00000 0.05 0.43 Q5 1 0.6988 0.1292 0.4984 11.00000 0.05 0.42 Q6 1 0.7434 0.1320 0.8334 11.00000 0.05 0.41 Q7 1 0.6429 0.1452 0.8550 11.00000 0.05 0.38 Q8 1 0.3238 0.2357 0.4608 11.00000 0.05 0.37 Q9 1 0.2940 0.0644 0.6471 11.00000 0.05 0.37 Q10 1 0.1699 0.0680 0.6554 11.00000 0.05 0.36 Q11 1 0.8418 0.1191 0.9092 11.00000 0.05 0.36 Q12 1 0.4456 0.2401 0.6049 11.00000 0.05 0.35 Q13 1 0.3866 0.2039 0.5416 11.00000 0.05 0.34 Q14 1 0.3875 0.0528 0.7366 11.00000 0.05 0.34 Q15 1 0.4791 0.1696 0.6045 11.00000 0.05 0.33 Q16 1 0.4177 0.0595 0.6428 11.00000 0.05 0.33 Q17 1 0.2676 0.2690 0.4998 11.00000 0.05 0.31 Q18 1 0.9028 0.1760 0.4867 11.00000 0.05 0.31 Q19 1 0.6498 0.1599 0.9592 11.00000 0.05 0.31 Q20 1 0.3748 0.0203 0.8406 11.00000 0.05 0.30 ; _shelx_res_checksum 18053 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group P1 P 0.56883(6) 0.13987(3) 0.63979(6) 0.01720(12) Uani 1 1 d . . . . . C1 C 0.4708(2) 0.06698(10) 0.6019(2) 0.0180(4) Uani 1 1 d . . . . . H1A H 0.417167 0.066058 0.510468 0.022 Uiso 1 1 calc R U . . . H1B H 0.543517 0.032729 0.620192 0.022 Uiso 1 1 calc R U . . . C11 C 0.6669(2) 0.14133(11) 0.8043(2) 0.0194(4) Uani 1 1 d . . . . . C12 C 0.8154(3) 0.12285(11) 0.8439(2) 0.0219(4) Uani 1 1 d . . . . . H12 H 0.865824 0.115684 0.783438 0.026 Uiso 1 1 calc R U . . . C13 C 0.8884(3) 0.11509(12) 0.9710(2) 0.0246(5) Uani 1 1 d . . . . . H13 H 0.989074 0.102736 0.997672 0.030 Uiso 1 1 calc R U . . . C14 C 0.8155(3) 0.12522(12) 1.0598(2) 0.0266(5) Uani 1 1 d . . . . . H14 H 0.866359 0.119807 1.146973 0.032 Uiso 1 1 calc R U . . . C15 C 0.6678(3) 0.14332(12) 1.0215(2) 0.0269(5) Uani 1 1 d . . . . . H15 H 0.618305 0.150358 1.082617 0.032 Uiso 1 1 calc R U . . . C16 C 0.5929(3) 0.15110(11) 0.8943(2) 0.0234(5) Uani 1 1 d . . . . . H16 H 0.491840 0.162992 0.868167 0.028 Uiso 1 1 calc R U . . . C21 C 0.6974(2) 0.14687(10) 0.5510(2) 0.0183(4) Uani 1 1 d . . . . . C22 C 0.7108(3) 0.10111(11) 0.4671(2) 0.0229(4) Uani 1 1 d . . . . . H22 H 0.651787 0.064790 0.456056 0.028 Uiso 1 1 calc R U . . . C23 C 0.8115(3) 0.10879(12) 0.3991(2) 0.0255(5) Uani 1 1 d . . . . . H23 H 0.820689 0.077743 0.341510 0.031 Uiso 1 1 calc R U . . . C24 C 0.8979(3) 0.16185(12) 0.4160(2) 0.0256(5) Uani 1 1 d . . . . . H24 H 0.966459 0.166879 0.369975 0.031 Uiso 1 1 calc R U . . . C25 C 0.8848(3) 0.20757(12) 0.4995(3) 0.0276(5) Uani 1 1 d . . . . . H25 H 0.944123 0.243781 0.510407 0.033 Uiso 1 1 calc R U . . . C26 C 0.7844(3) 0.20035(11) 0.5673(3) 0.0253(5) Uani 1 1 d . . . . . H26 H 0.775093 0.231623 0.624490 0.030 Uiso 1 1 calc R U . . . C31 C 0.4426(3) 0.20372(11) 0.5945(2) 0.0215(4) Uani 1 1 d . . . . . C32 C 0.3426(3) 0.20253(12) 0.4725(3) 0.0267(5) Uani 1 1 d . . . . . H32 H 0.336379 0.167046 0.420704 0.032 Uiso 1 1 calc R U . . . C33 C 0.2522(3) 0.25361(14) 0.4274(3) 0.0342(6) Uani 1 1 d . . . . . H33 H 0.183895 0.252994 0.344849 0.041 Uiso 1 1 calc R U . . . C34 C 0.2622(3) 0.30533(14) 0.5036(4) 0.0397(7) Uani 1 1 d . . . . . H34 H 0.201147 0.340256 0.472479 0.048 Uiso 1 1 calc R U . . . C35 C 0.3600(4) 0.30651(13) 0.6241(3) 0.0387(7) Uani 1 1 d . . . . . H35 H 0.364938 0.341993 0.675680 0.046 Uiso 1 1 calc R U . . . C36 C 0.4520(3) 0.25585(12) 0.6707(3) 0.0297(5) Uani 1 1 d . . . . . H36 H 0.520155 0.256872 0.753354 0.036 Uiso 1 1 calc R U . . . C41 C 0.3619(2) 0.05617(10) 0.6745(2) 0.0178(4) Uani 1 1 d . . . . . C42 C 0.2133(3) 0.07168(12) 0.6213(2) 0.0232(4) Uani 1 1 d . . . . . H42 H 0.180598 0.089823 0.539691 0.028 Uiso 1 1 calc R U . . . C43 C 0.1128(3) 0.06064(13) 0.6876(3) 0.0269(5) Uani 1 1 d . . . . . H43 H 0.011490 0.070613 0.650292 0.032 Uiso 1 1 calc R U . . . C44 C 0.1600(3) 0.03517(12) 0.8076(3) 0.0260(5) Uani 1 1 d . . . . . H44 H 0.091464 0.028441 0.853084 0.031 Uiso 1 1 calc R U . . . C45 C 0.3074(3) 0.01955(12) 0.8611(2) 0.0239(5) Uani 1 1 d . . . . . H45 H 0.339869 0.002110 0.943376 0.029 Uiso 1 1 calc R U . . . C46 C 0.4085(3) 0.02939(11) 0.7943(2) 0.0216(4) Uani 1 1 d . . . . . H46 H 0.508994 0.017852 0.830569 0.026 Uiso 1 1 calc R U . . . B1 B 0.2207(3) 0.05262(12) 0.2513(3) 0.0207(5) Uani 1 1 d . . . . . F1 F 0.20196(19) 0.00124(8) 0.31879(17) 0.0361(4) Uani 1 1 d . . . . . F2 F 0.37044(16) 0.07129(7) 0.29901(15) 0.0274(3) Uani 1 1 d . . . . . F3 F 0.1902(2) 0.03882(9) 0.12451(16) 0.0391(4) Uani 1 1 d . . . . . F4 F 0.13282(18) 0.10155(8) 0.26775(17) 0.0347(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 0.0161(2) 0.0183(2) 0.0200(3) -0.0002(2) 0.00955(19) 0.00081(19) C1 0.0185(9) 0.0180(9) 0.0197(10) -0.0001(7) 0.0089(8) 0.0000(7) C11 0.0182(9) 0.0206(10) 0.0220(10) -0.0032(8) 0.0101(8) -0.0011(8) C12 0.0202(10) 0.0237(10) 0.0243(11) -0.0008(8) 0.0106(9) 0.0000(8) C13 0.0200(10) 0.0282(12) 0.0246(11) 0.0001(9) 0.0052(9) -0.0005(9) C14 0.0303(12) 0.0271(12) 0.0222(11) -0.0020(9) 0.0078(9) -0.0049(9) C15 0.0311(12) 0.0286(12) 0.0259(12) -0.0041(9) 0.0161(10) -0.0033(10) C16 0.0209(10) 0.0257(11) 0.0272(12) -0.0038(9) 0.0126(9) -0.0015(8) C21 0.0174(9) 0.0202(10) 0.0195(10) 0.0015(8) 0.0089(8) 0.0014(7) C22 0.0232(11) 0.0248(11) 0.0248(11) -0.0033(9) 0.0132(9) -0.0023(8) C23 0.0275(12) 0.0292(12) 0.0250(12) -0.0034(9) 0.0158(10) -0.0010(9) C24 0.0240(11) 0.0303(12) 0.0276(12) 0.0039(9) 0.0154(10) 0.0004(9) C25 0.0288(12) 0.0240(11) 0.0365(14) 0.0004(10) 0.0197(11) -0.0044(9) C26 0.0270(11) 0.0209(10) 0.0339(13) -0.0033(9) 0.0179(10) -0.0022(9) C31 0.0194(10) 0.0187(10) 0.0312(12) 0.0025(8) 0.0147(9) 0.0015(8) C32 0.0240(11) 0.0244(11) 0.0324(13) 0.0043(10) 0.0099(10) 0.0013(9) C33 0.0233(12) 0.0329(14) 0.0475(17) 0.0131(12) 0.0123(11) 0.0038(10) C34 0.0345(14) 0.0302(14) 0.065(2) 0.0158(14) 0.0309(15) 0.0141(11) C35 0.0476(17) 0.0232(12) 0.058(2) 0.0003(12) 0.0344(16) 0.0092(11) C36 0.0345(13) 0.0248(12) 0.0363(14) -0.0030(10) 0.0205(11) 0.0014(10) C41 0.0179(9) 0.0184(9) 0.0187(10) 0.0006(7) 0.0081(8) -0.0001(7) C42 0.0199(10) 0.0278(11) 0.0241(11) 0.0043(9) 0.0102(9) 0.0025(8) C43 0.0194(10) 0.0331(13) 0.0317(13) 0.0023(10) 0.0128(10) 0.0023(9) C44 0.0267(12) 0.0280(12) 0.0294(12) -0.0015(9) 0.0177(10) -0.0038(9) C45 0.0276(11) 0.0272(11) 0.0183(10) 0.0007(8) 0.0089(9) -0.0045(9) C46 0.0187(10) 0.0255(11) 0.0201(10) 0.0006(8) 0.0051(8) -0.0019(8) B1 0.0186(11) 0.0221(11) 0.0205(11) 0.0007(9) 0.0048(9) 0.0020(9) F1 0.0309(8) 0.0354(9) 0.0438(10) 0.0111(7) 0.0142(7) -0.0022(7) F2 0.0203(7) 0.0332(8) 0.0275(8) 0.0048(6) 0.0053(6) -0.0006(6) F3 0.0403(10) 0.0492(11) 0.0243(8) -0.0058(7) 0.0045(7) 0.0087(8) F4 0.0272(8) 0.0361(9) 0.0394(9) -0.0052(7) 0.0082(7) 0.0082(7) 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' 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 C11 P1 C31 111.72(11) . . ? C11 P1 C21 109.46(10) . . ? C31 P1 C21 106.80(10) . . ? C11 P1 C1 108.95(11) . . ? C31 P1 C1 110.43(11) . . ? C21 P1 C1 109.44(10) . . ? C41 C1 P1 113.40(15) . . ? C41 C1 H1A 108.9 . . ? P1 C1 H1A 108.9 . . ? C41 C1 H1B 108.9 . . ? P1 C1 H1B 108.9 . . ? H1A C1 H1B 107.7 . . ? C12 C11 C16 119.6(2) . . ? C12 C11 P1 118.55(17) . . ? C16 C11 P1 121.07(18) . . ? C13 C12 C11 119.9(2) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.4(2) . . ? C12 C13 H13 119.8 . . ? C14 C13 H13 119.8 . . ? C13 C14 C15 120.1(2) . . ? C13 C14 H14 119.9 . . ? C15 C14 H14 119.9 . . ? C16 C15 C14 120.2(2) . . ? C16 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C15 C16 C11 119.8(2) . . ? C15 C16 H16 120.1 . . ? C11 C16 H16 120.1 . . ? C22 C21 C26 120.1(2) . . ? C22 C21 P1 121.74(17) . . ? C26 C21 P1 118.14(17) . . ? C21 C22 C23 119.8(2) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C24 C23 C22 119.9(2) . . ? C24 C23 H23 120.0 . . ? C22 C23 H23 120.0 . . ? C25 C24 C23 120.5(2) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C26 120.0(2) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 119.8(2) . . ? C25 C26 H26 120.1 . . ? C21 C26 H26 120.1 . . ? C36 C31 C32 120.2(2) . . ? C36 C31 P1 122.3(2) . . ? C32 C31 P1 117.16(19) . . ? C33 C32 C31 119.8(3) . . ? C33 C32 H32 120.1 . . ? C31 C32 H32 120.1 . . ? C34 C33 C32 119.8(3) . . ? C34 C33 H33 120.1 . . ? C32 C33 H33 120.1 . . ? C35 C34 C33 120.6(3) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C34 C35 C36 120.4(3) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C31 C36 C35 119.2(3) . . ? C31 C36 H36 120.4 . . ? C35 C36 H36 120.4 . . ? C42 C41 C46 119.3(2) . . ? C42 C41 C1 120.4(2) . . ? C46 C41 C1 120.3(2) . . ? C43 C42 C41 120.2(2) . . ? C43 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? C44 C43 C42 120.3(2) . . ? C44 C43 H43 119.8 . . ? C42 C43 H43 119.8 . . ? C43 C44 C45 119.9(2) . . ? C43 C44 H44 120.1 . . ? C45 C44 H44 120.1 . . ? C44 C45 C46 120.2(2) . . ? C44 C45 H45 119.9 . . ? C46 C45 H45 119.9 . . ? C41 C46 C45 120.1(2) . . ? C41 C46 H46 120.0 . . ? C45 C46 H46 120.0 . . ? F1 B1 F3 111.1(2) . . ? F1 B1 F4 110.8(2) . . ? F3 B1 F4 110.5(2) . . ? F1 B1 F2 107.8(2) . . ? F3 B1 F2 108.5(2) . . ? F4 B1 F2 108.0(2) . . ? 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 C11 1.784(2) . ? P1 C31 1.796(2) . ? P1 C21 1.797(2) . ? P1 C1 1.812(2) . ? C1 C41 1.513(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C11 C12 1.402(3) . ? C11 C16 1.404(3) . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.386(4) . ? C13 H13 0.9500 . ? C14 C15 1.392(4) . ? C14 H14 0.9500 . ? C15 C16 1.387(4) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C21 C22 1.391(3) . ? C21 C26 1.399(3) . ? C22 C23 1.399(3) . ? C22 H22 0.9500 . ? C23 C24 1.389(4) . ? C23 H23 0.9500 . ? C24 C25 1.387(4) . ? C24 H24 0.9500 . ? C25 C26 1.394(3) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C31 C36 1.396(3) . ? C31 C32 1.399(4) . ? C32 C33 1.394(4) . ? C32 H32 0.9500 . ? C33 C34 1.387(5) . ? C33 H33 0.9500 . ? C34 C35 1.380(5) . ? C34 H34 0.9500 . ? C35 C36 1.398(4) . ? C35 H35 0.9500 . ? C36 H36 0.9500 . ? C41 C42 1.395(3) . ? C41 C46 1.396(3) . ? C42 C43 1.394(3) . ? C42 H42 0.9500 . ? C43 C44 1.387(4) . ? C43 H43 0.9500 . ? C44 C45 1.387(4) . ? C44 H44 0.9500 . ? C45 C46 1.398(3) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? B1 F1 1.381(3) . ? B1 F3 1.384(3) . ? B1 F4 1.393(3) . ? B1 F2 1.417(3) . ? 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 C11 P1 C1 C41 59.11(19) . . . . ? C31 P1 C1 C41 -63.94(19) . . . . ? C21 P1 C1 C41 178.76(16) . . . . ? C31 P1 C11 C12 -143.03(18) . . . . ? C21 P1 C11 C12 -24.9(2) . . . . ? C1 P1 C11 C12 94.7(2) . . . . ? C31 P1 C11 C16 47.0(2) . . . . ? C21 P1 C11 C16 165.04(19) . . . . ? C1 P1 C11 C16 -75.3(2) . . . . ? C16 C11 C12 C13 -0.7(4) . . . . ? P1 C11 C12 C13 -170.91(19) . . . . ? C11 C12 C13 C14 0.3(4) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C13 C14 C15 C16 0.2(4) . . . . ? C14 C15 C16 C11 -0.7(4) . . . . ? C12 C11 C16 C15 1.0(4) . . . . ? P1 C11 C16 C15 170.88(19) . . . . ? C11 P1 C21 C22 119.9(2) . . . . ? C31 P1 C21 C22 -119.0(2) . . . . ? C1 P1 C21 C22 0.6(2) . . . . ? C11 P1 C21 C26 -60.6(2) . . . . ? C31 P1 C21 C26 60.5(2) . . . . ? C1 P1 C21 C26 -179.91(19) . . . . ? C26 C21 C22 C23 -0.1(4) . . . . ? P1 C21 C22 C23 179.4(2) . . . . ? C21 C22 C23 C24 0.3(4) . . . . ? C22 C23 C24 C25 -0.3(4) . . . . ? C23 C24 C25 C26 0.1(4) . . . . ? C24 C25 C26 C21 0.1(4) . . . . ? C22 C21 C26 C25 -0.1(4) . . . . ? P1 C21 C26 C25 -179.6(2) . . . . ? C11 P1 C31 C36 16.5(2) . . . . ? C21 P1 C31 C36 -103.1(2) . . . . ? C1 P1 C31 C36 138.0(2) . . . . ? C11 P1 C31 C32 -170.18(18) . . . . ? C21 P1 C31 C32 70.2(2) . . . . ? C1 P1 C31 C32 -48.8(2) . . . . ? C36 C31 C32 C33 -0.1(4) . . . . ? P1 C31 C32 C33 -173.5(2) . . . . ? C31 C32 C33 C34 0.2(4) . . . . ? C32 C33 C34 C35 -0.6(4) . . . . ? C33 C34 C35 C36 0.8(4) . . . . ? C32 C31 C36 C35 0.3(4) . . . . ? P1 C31 C36 C35 173.4(2) . . . . ? C34 C35 C36 C31 -0.7(4) . . . . ? P1 C1 C41 C42 95.2(2) . . . . ? P1 C1 C41 C46 -86.1(2) . . . . ? C46 C41 C42 C43 0.2(4) . . . . ? C1 C41 C42 C43 178.9(2) . . . . ? C41 C42 C43 C44 1.1(4) . . . . ? C42 C43 C44 C45 -1.2(4) . . . . ? C43 C44 C45 C46 0.0(4) . . . . ? C42 C41 C46 C45 -1.4(4) . . . . ? C1 C41 C46 C45 179.9(2) . . . . ? C44 C45 C46 C41 1.3(4) . . . . ?