#------------------------------------------------------------------------------ #$Date: 2024-10-03 03:59:37 +0300 (Thu, 03 Oct 2024) $ #$Revision: 295002 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/94/7249419.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_7249419 loop_ _publ_author_name 'Kumar, sharvan' 'Mandal, Kalyanshis' 'Ajayakumar, M. R.' 'Hundal, Geeta' 'Mukhopadhyay, Pritam' _publ_section_title ; Unravelling the Intramolecular n\\rightarrow \s* Interaction in Ultra-Electron Deficient Naphthalenediimides and their Radical Ions ; _journal_name_full 'Physical Chemistry Chemical Physics' _journal_paper_doi 10.1039/D4CP02834A _journal_year 2024 _chemical_formula_moiety 'C68 H70 N2 O10 P2, 2(B F4)' _chemical_formula_sum 'C68 H70 B2 F8 N2 O10 P2' _chemical_formula_weight 1310.82 _chemical_name_common Naphthalenediimide-bis-methoxyphenylphosphonium _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2015-02-21 deposited with the CCDC. 2024-10-02 downloaded from the CCDC. ; _cell_angle_alpha 92.111(5) _cell_angle_beta 94.947(7) _cell_angle_gamma 92.151(5) _cell_formula_units_Z 1 _cell_length_a 10.2080(8) _cell_length_b 12.3079(5) _cell_length_c 13.6327(11) _cell_measurement_reflns_used 14110 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 29 _cell_measurement_theta_min 2 _cell_volume 1703.8(2) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SIR-92(Altomare et. al.,1993)' _diffrn_ambient_temperature 295(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.849 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_unetI/netI 0.0657 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.849 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 15341 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.849 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.302 _diffrn_reflns_theta_min 2.902 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_T_max 0.995 _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2008/1 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.278 _exptl_crystal_description Block _exptl_crystal_F_000 684 _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.170 _exptl_crystal_size_min 0.110 _platon_squeeze_details ; The sixteen electron recovered could be due to a methanol or 1.5 water molecules. The volume of the void created matches well with the SAV of 99 A3 shown by PLATON. ; _refine_diff_density_max 0.989 _refine_diff_density_min -0.426 _refine_diff_density_rms 0.068 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 441 _refine_ls_number_reflns 7902 _refine_ls_number_restraints 30 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.1305 _refine_ls_R_factor_gt 0.0873 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2728 _refine_ls_wR_factor_ref 0.3127 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4725 _reflns_number_total 7902 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4cp02834a2.cif _cod_data_source_block shelx _cod_database_code 7249419 _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 0.971 _shelx_estimated_absorpt_t_max 0.984 _shelxl_version_number 2013-4 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 C1 C 0.3557(3) 0.4668(2) 0.4083(2) 0.0383(7) Uani 1 1 d . . . . . C2 C 0.4062(3) 0.3859(2) 0.3490(2) 0.0388(6) Uani 1 1 d . . . . . C3 C 0.4628(3) 0.6433(3) 0.6286(2) 0.0422(7) Uani 1 1 d . . . . . H3 H 0.4283 0.6968 0.6677 0.051 Uiso 1 1 calc R U . . . C4 C 0.3841(3) 0.5948(2) 0.5507(2) 0.0391(7) Uani 1 1 d . . . . . C5 C 0.4348(3) 0.5156(2) 0.4889(2) 0.0367(6) Uani 1 1 d . . . . . C6 C 0.2195(3) 0.5027(3) 0.3875(2) 0.0415(7) Uani 1 1 d . . . . . C7 C 0.2481(3) 0.6285(3) 0.5330(2) 0.0466(8) Uani 1 1 d . . . . . C8 C 0.0391(3) 0.6214(3) 0.4275(3) 0.0558(9) Uani 1 1 d . . . . . H8A H -0.0032 0.6279 0.4883 0.067 Uiso 1 1 calc R U . . . H8B H -0.0114 0.5675 0.3846 0.067 Uiso 1 1 calc R U . . . C9 C 0.0372(5) 0.7298(4) 0.3786(3) 0.0818(14) Uani 1 1 d . . . . . H9A H -0.0529 0.7529 0.3721 0.098 Uiso 1 1 calc R U . . . H9B H 0.0881 0.7830 0.4220 0.098 Uiso 1 1 calc R U . . . C10 C 0.0889(6) 0.7321(4) 0.2799(4) 0.0980(16) Uani 1 1 d . . . . . H10A H 0.0401 0.6780 0.2362 0.118 Uiso 1 1 calc R U . . . H10B H 0.1804 0.7125 0.2861 0.118 Uiso 1 1 calc R U . . . C11 C 0.0794(9) 0.8417(6) 0.2344(5) 0.142(3) Uani 1 1 d D . . . . H11A H 0.1416 0.8933 0.2705 0.171 Uiso 0.33(17) 1 calc R U P A 1 H11B H -0.0084 0.8680 0.2391 0.171 Uiso 0.33(17) 1 calc R U P A 1 H11C H 0.1062 0.8961 0.2863 0.171 Uiso 0.67(17) 1 calc R U P A 2 H11D H -0.0131 0.8516 0.2155 0.171 Uiso 0.67(17) 1 calc R U P A 2 C12 C 0.109(3) 0.8339(18) 0.1260(11) 0.156(8) Uani 0.519(9) 1 d D . P B 1 H12A H 0.2023 0.8257 0.1228 0.187 Uiso 0.519(9) 1 calc R U P B 1 H12B H 0.0633 0.7693 0.0948 0.187 Uiso 0.519(9) 1 calc R U P B 1 C12' C 0.154(3) 0.870(2) 0.1461(13) 0.156(8) Uani 0.481(9) 1 d D . P B 2 H12C H 0.1623 0.9477 0.1390 0.187 Uiso 0.481(9) 1 calc R U P B 2 H12D H 0.2412 0.8401 0.1512 0.187 Uiso 0.481(9) 1 calc R U P B 2 C13 C 0.0673(15) 0.9318(11) 0.0690(9) 0.126(3) Uani 0.519(9) 1 d D . P B 1 H13A H 0.1204 0.9396 0.0147 0.189 Uiso 0.519(9) 1 calc R U P B 1 H13B H 0.0788 0.9960 0.1116 0.189 Uiso 0.519(9) 1 calc R U P B 1 H13C H -0.0236 0.9221 0.0445 0.189 Uiso 0.519(9) 1 calc R U P B 1 C13' C 0.0681(16) 0.8156(13) 0.0630(12) 0.126(3) Uani 0.481(9) 1 d D . P B 2 H13D H 0.1195 0.8002 0.0088 0.189 Uiso 0.481(9) 1 calc R U P B 2 H13E H -0.0008 0.8630 0.0424 0.189 Uiso 0.481(9) 1 calc R U P B 2 H13F H 0.0300 0.7490 0.0843 0.189 Uiso 0.481(9) 1 calc R U P B 2 C14 C 0.1789(3) 0.2385(3) 0.2890(2) 0.0428(7) Uani 1 1 d . . . . . C15 C 0.1971(4) 0.1945(3) 0.3820(3) 0.0554(9) Uani 1 1 d . . . . . H15 H 0.2758 0.2082 0.4209 0.066 Uiso 1 1 calc R U . . . C16 C 0.0978(4) 0.1307(3) 0.4158(3) 0.0605(10) Uani 1 1 d . . . . . H16 H 0.1109 0.1002 0.4771 0.073 Uiso 1 1 calc R U . . . C17 C -0.0195(4) 0.1116(3) 0.3606(3) 0.0522(8) Uani 1 1 d . . . . . C18 C -0.0399(3) 0.1557(3) 0.2696(3) 0.0555(9) Uani 1 1 d . . . . . H18 H -0.1199 0.1430 0.2322 0.067 Uiso 1 1 calc R U . . . C19 C 0.0581(4) 0.2187(3) 0.2342(2) 0.0530(8) Uani 1 1 d . . . . . H19 H 0.0437 0.2486 0.1727 0.064 Uiso 1 1 calc R U . . . C20 C -0.2366(5) 0.0315(4) 0.3514(4) 0.0939(16) Uani 1 1 d . . . . . H20A H -0.2904 -0.0132 0.3895 0.141 Uiso 1 1 calc R U . . . H20B H -0.2281 -0.0046 0.2887 0.141 Uiso 1 1 calc R U . . . H20C H -0.2769 0.0999 0.3412 0.141 Uiso 1 1 calc R U . . . C21 C 0.2777(3) 0.3995(2) 0.1447(2) 0.0435(7) Uani 1 1 d . . . . . C22 C 0.2177(4) 0.3550(3) 0.0556(2) 0.0554(9) Uani 1 1 d . . . . . H22 H 0.1936 0.2812 0.0507 0.067 Uiso 1 1 calc R U . . . C24 C 0.1935(4) 0.4170(3) -0.0248(3) 0.0611(10) Uani 1 1 d . . . . . H24 H 0.1501 0.3864 -0.0826 0.073 Uiso 1 1 calc R U . . . C25 C 0.2346(4) 0.5268(3) -0.0192(3) 0.0589(9) Uani 1 1 d . . . . . C26 C 0.2984(5) 0.5710(3) 0.0673(3) 0.0704(12) Uani 1 1 d . . . . . H26 H 0.3273 0.6437 0.0708 0.084 Uiso 1 1 calc R U . . . C27 C 0.3197(4) 0.5082(3) 0.1490(3) 0.0620(10) Uani 1 1 d . . . . . H27 H 0.3624 0.5390 0.2070 0.074 Uiso 1 1 calc R U . . . C28 C 0.1568(7) 0.5537(4) -0.1871(3) 0.0985(17) Uani 1 1 d . . . . . H28A H 0.1523 0.6110 -0.2330 0.148 Uiso 1 1 calc R U . . . H28B H 0.0695 0.5257 -0.1790 0.148 Uiso 1 1 calc R U . . . H28C H 0.2078 0.4964 -0.2117 0.148 Uiso 1 1 calc R U . . . C29 C 0.4202(3) 0.2142(3) 0.1980(2) 0.0446(7) Uani 1 1 d . . . . . C30 C 0.5230(4) 0.2499(3) 0.1429(3) 0.0547(9) Uani 1 1 d . . . . . H30 H 0.5342 0.3234 0.1310 0.066 Uiso 1 1 calc R U . . . C31 C 0.6066(4) 0.1764(3) 0.1068(3) 0.0638(10) Uani 1 1 d . . . . . H31 H 0.6756 0.2006 0.0719 0.077 Uiso 1 1 calc R U . . . C32 C 0.5888(4) 0.0668(3) 0.1220(3) 0.0618(10) Uani 1 1 d . . . . . C33 C 0.4870(4) 0.0297(3) 0.1759(3) 0.0625(10) Uani 1 1 d . . . . . H33 H 0.4748 -0.0441 0.1865 0.075 Uiso 1 1 calc R U . . . C34 C 0.4050(4) 0.1044(3) 0.2129(3) 0.0537(8) Uani 1 1 d . . . . . H34 H 0.3374 0.0800 0.2491 0.064 Uiso 1 1 calc R U . . . C35 C 0.6610(6) -0.1139(4) 0.0938(4) 0.107(2) Uani 1 1 d . . . . . H35A H 0.7295 -0.1501 0.0632 0.160 Uiso 1 1 calc R U . . . H35B H 0.5770 -0.1389 0.0622 0.160 Uiso 1 1 calc R U . . . H35C H 0.6653 -0.1300 0.1623 0.160 Uiso 1 1 calc R U . . . O1 O 0.1496(2) 0.46407(19) 0.31667(16) 0.0526(6) Uani 1 1 d . . . . . O2 O 0.1993(3) 0.6922(2) 0.58748(19) 0.0683(8) Uani 1 1 d . . . . . O3 O -0.1111(3) 0.0498(2) 0.4021(2) 0.0746(8) Uani 1 1 d . . . . . O4 O 0.2174(4) 0.5953(2) -0.0942(2) 0.0836(10) Uani 1 1 d . . . . . O5 O 0.6777(3) 0.0024(3) 0.0841(2) 0.0892(10) Uani 1 1 d . . . . . P1 P 0.31334(8) 0.31295(6) 0.24506(5) 0.0403(3) Uani 1 1 d . . . . . N1 N 0.1743(2) 0.5828(2) 0.44974(19) 0.0448(6) Uani 1 1 d . . . . . B1 B 0.645(2) 0.6919(16) 0.3298(13) 0.452(15) Uani 0.617(5) 1 d D U P C 1 F1 F 0.6130(18) 0.7399(13) 0.4058(10) 0.300(7) Uani 0.617(5) 1 d D . P C 1 F2 F 0.7233(13) 0.6218(9) 0.3807(9) 0.245(5) Uani 0.617(5) 1 d D . P C 1 F3 F 0.7212(11) 0.7235(10) 0.2620(9) 0.230(5) Uani 0.617(5) 1 d D . P C 1 F4 F 0.5722(12) 0.6100(7) 0.2983(7) 0.189(4) Uani 0.617(5) 1 d D . P C 1 B1' B 0.580(2) 0.697(2) 0.3220(19) 0.452(15) Uani 0.383(5) 1 d D U P C 2 F1' F 0.503(2) 0.7504(17) 0.2484(14) 0.300(7) Uani 0.383(5) 1 d D . P C 2 F2' F 0.651(2) 0.7897(16) 0.3323(15) 0.245(5) Uani 0.383(5) 1 d D . P C 2 F3' F 0.6260(19) 0.6422(16) 0.2452(15) 0.230(5) Uani 0.383(5) 1 d D . P C 2 F4' F 0.4569(15) 0.6813(12) 0.3361(11) 0.189(4) Uani 0.383(5) 1 d D . 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 C1 0.0395(16) 0.0401(15) 0.0343(14) -0.0012(12) -0.0006(12) 0.0016(12) C2 0.0403(16) 0.0421(15) 0.0333(14) -0.0033(12) 0.0008(12) 0.0015(12) C3 0.0444(17) 0.0445(16) 0.0366(15) -0.0047(13) 0.0002(12) 0.0030(13) C4 0.0395(16) 0.0429(16) 0.0345(14) -0.0028(12) 0.0008(12) 0.0056(12) C5 0.0376(15) 0.0388(15) 0.0329(14) -0.0012(12) -0.0001(11) 0.0006(12) C6 0.0415(16) 0.0455(17) 0.0367(15) -0.0017(13) 0.0001(12) 0.0040(13) C7 0.0433(18) 0.0555(19) 0.0403(16) -0.0067(14) -0.0009(13) 0.0110(15) C8 0.0413(18) 0.069(2) 0.056(2) -0.0073(17) -0.0071(15) 0.0135(16) C9 0.072(3) 0.092(3) 0.081(3) 0.001(3) -0.007(2) 0.032(3) C10 0.117(4) 0.089(4) 0.087(4) -0.002(3) -0.005(3) 0.025(3) C11 0.196(8) 0.108(5) 0.132(6) 0.050(5) 0.030(5) 0.049(5) C12 0.27(2) 0.114(15) 0.087(8) 0.010(9) 0.006(11) 0.034(13) C12' 0.27(2) 0.114(15) 0.087(8) 0.010(9) 0.006(11) 0.034(13) C13 0.160(9) 0.125(7) 0.099(6) 0.029(7) 0.027(6) 0.011(7) C13' 0.160(9) 0.125(7) 0.099(6) 0.029(7) 0.027(6) 0.011(7) C14 0.0465(17) 0.0436(16) 0.0375(15) -0.0025(13) 0.0000(13) 0.0020(13) C15 0.052(2) 0.065(2) 0.0480(19) 0.0072(17) -0.0055(15) -0.0025(16) C16 0.052(2) 0.076(2) 0.054(2) 0.0193(19) -0.0025(16) -0.0041(18) C17 0.054(2) 0.0484(19) 0.054(2) 0.0034(16) 0.0047(16) -0.0017(15) C18 0.0422(18) 0.069(2) 0.053(2) 0.0013(17) -0.0066(15) -0.0058(16) C19 0.056(2) 0.061(2) 0.0396(17) 0.0042(15) -0.0025(15) -0.0026(16) C20 0.065(3) 0.097(4) 0.117(4) 0.025(3) -0.010(3) -0.028(2) C21 0.0501(18) 0.0402(16) 0.0386(15) -0.0037(13) -0.0024(13) 0.0021(13) C22 0.078(3) 0.0454(18) 0.0398(17) -0.0025(14) -0.0081(16) -0.0071(17) C24 0.080(3) 0.058(2) 0.0415(18) 0.0015(16) -0.0115(17) -0.0114(19) C25 0.076(3) 0.049(2) 0.050(2) 0.0082(16) -0.0023(17) -0.0035(18) C26 0.106(3) 0.048(2) 0.053(2) 0.0083(17) -0.008(2) -0.018(2) C27 0.080(3) 0.055(2) 0.0458(19) -0.0046(16) -0.0089(17) -0.0169(18) C28 0.147(5) 0.091(3) 0.053(2) 0.014(2) -0.026(3) 0.001(3) C29 0.0503(18) 0.0439(17) 0.0381(15) -0.0053(13) -0.0018(13) -0.0002(14) C30 0.057(2) 0.056(2) 0.0515(19) 0.0030(16) 0.0076(16) 0.0000(16) C31 0.062(2) 0.075(3) 0.056(2) 0.0040(19) 0.0161(18) 0.011(2) C32 0.069(2) 0.071(3) 0.0453(19) -0.0100(18) 0.0022(17) 0.017(2) C33 0.068(2) 0.0448(19) 0.072(2) -0.0096(17) -0.004(2) 0.0033(17) C34 0.054(2) 0.0484(19) 0.057(2) -0.0058(16) 0.0051(16) -0.0035(15) C35 0.119(5) 0.084(3) 0.114(4) -0.039(3) -0.011(3) 0.046(3) O1 0.0476(13) 0.0587(14) 0.0483(13) -0.0103(11) -0.0107(10) 0.0058(11) O2 0.0528(15) 0.091(2) 0.0591(15) -0.0285(14) -0.0042(12) 0.0264(14) O3 0.0626(17) 0.0785(19) 0.0820(19) 0.0281(16) 0.0002(14) -0.0168(14) O4 0.123(3) 0.0618(17) 0.0627(17) 0.0196(14) -0.0147(17) -0.0107(17) O5 0.096(2) 0.095(2) 0.080(2) -0.0115(17) 0.0167(17) 0.0436(19) P1 0.0445(5) 0.0406(5) 0.0343(4) -0.0034(3) -0.0020(3) -0.0011(3) N1 0.0353(14) 0.0533(16) 0.0443(14) -0.0061(12) -0.0029(11) 0.0068(12) B1 0.73(3) 0.45(3) 0.128(12) 0.168(16) -0.139(19) -0.40(3) F1 0.46(2) 0.251(11) 0.179(9) -0.010(9) 0.002(12) -0.089(14) F2 0.311(12) 0.207(9) 0.222(10) 0.044(7) 0.094(9) -0.124(9) F3 0.207(9) 0.240(11) 0.254(10) 0.113(9) 0.058(8) -0.029(7) F4 0.242(11) 0.156(7) 0.153(7) 0.047(6) -0.053(7) -0.079(6) B1' 0.73(3) 0.45(3) 0.128(12) 0.168(16) -0.139(19) -0.40(3) F1' 0.46(2) 0.251(11) 0.179(9) -0.010(9) 0.002(12) -0.089(14) F2' 0.311(12) 0.207(9) 0.222(10) 0.044(7) 0.094(9) -0.124(9) F3' 0.207(9) 0.240(11) 0.254(10) 0.113(9) 0.058(8) -0.029(7) F4' 0.242(11) 0.156(7) 0.153(7) 0.047(6) -0.053(7) -0.079(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 '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' 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 C2 C1 C5 120.0(3) . . ? C2 C1 C6 121.0(3) . . ? C5 C1 C6 119.0(3) . . ? C1 C2 C3 118.4(3) . 2_666 ? C1 C2 P1 124.6(2) . . ? C3 C2 P1 117.0(2) 2_666 . ? C4 C3 C2 122.0(3) . 2_666 ? C4 C3 H3 119.0 . . ? C2 C3 H3 119.0 2_666 . ? C3 C4 C5 120.2(3) . . ? C3 C4 C7 118.7(3) . . ? C5 C4 C7 121.1(3) . . ? C4 C5 C1 120.6(3) . . ? C4 C5 C5 118.5(3) . 2_666 ? C1 C5 C5 120.9(3) . 2_666 ? O1 C6 N1 121.0(3) . . ? O1 C6 C1 120.6(3) . . ? N1 C6 C1 118.4(3) . . ? O2 C7 N1 120.2(3) . . ? O2 C7 C4 122.8(3) . . ? N1 C7 C4 117.0(3) . . ? N1 C8 C9 113.0(3) . . ? N1 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N1 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C10 C9 C8 116.1(4) . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9B 108.3 . . ? C8 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? C9 C10 C11 113.0(5) . . ? C9 C10 H10A 109.0 . . ? C11 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? C11 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? C10 C11 C12' 121.4(13) . . ? C10 C11 C12 110.7(9) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C10 C11 H11C 107.0 . . ? C12' C11 H11C 107.0 . . ? C10 C11 H11D 107.0 . . ? C12' C11 H11D 107.0 . . ? H11C C11 H11D 106.7 . . ? C13 C12 C11 113.4(15) . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12B 108.9 . . ? C11 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C13' C12' C11 101.7(15) . . ? C13' C12' H12C 111.4 . . ? C11 C12' H12C 111.4 . . ? C13' C12' H12D 111.4 . . ? C11 C12' H12D 111.4 . . ? H12C C12' H12D 109.3 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12' C13' H13D 109.5 . . ? C12' C13' H13E 109.5 . . ? H13D C13' H13E 109.5 . . ? C12' C13' H13F 109.5 . . ? H13D C13' H13F 109.5 . . ? H13E C13' H13F 109.5 . . ? C19 C14 C15 118.4(3) . . ? C19 C14 P1 123.4(2) . . ? C15 C14 P1 118.2(3) . . ? C16 C15 C14 119.7(3) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C17 C16 C15 121.0(3) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? O3 C17 C16 115.9(3) . . ? O3 C17 C18 124.0(3) . . ? C16 C17 C18 120.1(3) . . ? C19 C18 C17 119.9(3) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C14 121.0(3) . . ? C18 C19 H19 119.5 . . ? C14 C19 H19 119.5 . . ? O3 C20 H20A 109.5 . . ? O3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C27 C21 C22 118.3(3) . . ? C27 C21 P1 121.8(3) . . ? C22 C21 P1 119.5(2) . . ? C24 C22 C21 121.7(3) . . ? C24 C22 H22 119.1 . . ? C21 C22 H22 119.1 . . ? C22 C24 C25 119.4(3) . . ? C22 C24 H24 120.3 . . ? C25 C24 H24 120.3 . . ? O4 C25 C26 116.0(3) . . ? O4 C25 C24 124.5(3) . . ? C26 C25 C24 119.5(3) . . ? C25 C26 C27 120.7(4) . . ? C25 C26 H26 119.7 . . ? C27 C26 H26 119.7 . . ? C21 C27 C26 120.3(3) . . ? C21 C27 H27 119.9 . . ? C26 C27 H27 119.9 . . ? O4 C28 H28A 109.5 . . ? O4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C34 C29 C30 118.4(3) . . ? C34 C29 P1 122.7(3) . . ? C30 C29 P1 118.9(3) . . ? C31 C30 C29 120.1(3) . . ? C31 C30 H30 119.9 . . ? C29 C30 H30 119.9 . . ? C30 C31 C32 120.4(4) . . ? C30 C31 H31 119.8 . . ? C32 C31 H31 119.8 . . ? O5 C32 C31 115.2(4) . . ? O5 C32 C33 124.5(4) . . ? C31 C32 C33 120.3(3) . . ? C34 C33 C32 118.7(4) . . ? C34 C33 H33 120.6 . . ? C32 C33 H33 120.6 . . ? C33 C34 C29 122.0(4) . . ? C33 C34 H34 119.0 . . ? C29 C34 H34 119.0 . . ? O5 C35 H35A 109.5 . . ? O5 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? O5 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C17 O3 C20 118.9(3) . . ? C25 O4 C28 118.9(3) . . ? C32 O5 C35 117.9(4) . . ? C14 P1 C21 117.48(15) . . ? C14 P1 C29 106.68(15) . . ? C21 P1 C29 104.43(14) . . ? C14 P1 C2 108.86(14) . . ? C21 P1 C2 111.76(14) . . ? C29 P1 C2 106.93(14) . . ? C6 N1 C7 123.8(2) . . ? C6 N1 C8 118.6(3) . . ? C7 N1 C8 117.6(3) . . ? F1 B1 F4 116.0(17) . . ? F1 B1 F3 131.2(18) . . ? F4 B1 F3 110.7(15) . . ? F1 B1 F2 93.8(13) . . ? F4 B1 F2 87.7(14) . . ? F3 B1 F2 101.6(15) . . ? F4' B1' F2' 128(2) . . ? F4' B1' F3' 117.6(19) . . ? F2' B1' F3' 105.1(19) . . ? F4' B1' F1' 71.8(14) . . ? F2' B1' F1' 85.1(17) . . ? F3' B1' F1' 84.6(16) . . ? B1' F1' F4' 50.7(9) . . ? B1' F4' F1' 57.5(11) . . ? 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 C1 C2 1.400(4) . ? C1 C5 1.407(4) . ? C1 C6 1.482(4) . ? C2 C3 1.408(4) 2_666 ? C2 P1 1.823(3) . ? C3 C4 1.378(4) . ? C3 C2 1.408(4) 2_666 ? C3 H3 0.9300 . ? C4 C5 1.407(4) . ? C4 C7 1.467(4) . ? C5 C5 1.411(6) 2_666 ? C6 O1 1.220(4) . ? C6 N1 1.395(4) . ? C7 O2 1.210(4) . ? C7 N1 1.396(4) . ? C8 N1 1.486(4) . ? C8 C9 1.514(6) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.488(7) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.508(8) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12' 1.523(18) . ? C11 C12 1.534(16) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C11 H11C 0.9700 . ? C11 H11D 0.9700 . ? C12 C13 1.512(19) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C12' C13' 1.493(18) . ? C12' H12C 0.9700 . ? C12' H12D 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C13' H13D 0.9600 . ? C13' H13E 0.9600 . ? C13' H13F 0.9600 . ? C14 C19 1.394(5) . ? C14 C15 1.397(5) . ? C14 P1 1.781(3) . ? C15 C16 1.380(5) . ? C15 H15 0.9300 . ? C16 C17 1.365(5) . ? C16 H16 0.9300 . ? C17 O3 1.358(4) . ? C17 C18 1.375(5) . ? C18 C19 1.374(5) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 O3 1.409(5) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 C27 1.387(5) . ? C21 C22 1.396(4) . ? C21 P1 1.786(3) . ? C22 C24 1.369(5) . ? C22 H22 0.9300 . ? C24 C25 1.397(5) . ? C24 H24 0.9300 . ? C25 O4 1.352(4) . ? C25 C26 1.380(5) . ? C26 C27 1.387(5) . ? C26 H26 0.9300 . ? C27 H27 0.9300 . ? C28 O4 1.430(5) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 C34 1.379(5) . ? C29 C30 1.408(5) . ? C29 P1 1.801(3) . ? C30 C31 1.374(5) . ? C30 H30 0.9300 . ? C31 C32 1.379(6) . ? C31 H31 0.9300 . ? C32 O5 1.350(4) . ? C32 C33 1.395(6) . ? C33 C34 1.378(5) . ? C33 H33 0.9300 . ? C34 H34 0.9300 . ? C35 O5 1.448(6) . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? B1 F1 1.248(16) . ? B1 F4 1.268(17) . ? B1 F3 1.319(16) . ? B1 F2 1.366(18) . ? B1' F4' 1.293(18) . ? B1' F2' 1.323(18) . ? B1' F3' 1.356(19) . ? B1' F1' 1.410(19) . ? F1' F4' 1.59(2) . ? 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 C1 C2 C3 -0.9(4) . . . 2_666 ? C6 C1 C2 C3 178.8(3) . . . 2_666 ? C5 C1 C2 P1 178.0(2) . . . . ? C6 C1 C2 P1 -2.3(4) . . . . ? C2 C3 C4 C5 -1.7(5) 2_666 . . . ? C2 C3 C4 C7 179.1(3) 2_666 . . . ? C3 C4 C5 C1 -179.2(3) . . . . ? C7 C4 C5 C1 0.0(5) . . . . ? C3 C4 C5 C5 2.5(5) . . . 2_666 ? C7 C4 C5 C5 -178.3(3) . . . 2_666 ? C2 C1 C5 C4 -178.2(3) . . . . ? C6 C1 C5 C4 2.1(4) . . . . ? C2 C1 C5 C5 0.0(5) . . . 2_666 ? C6 C1 C5 C5 -179.7(3) . . . 2_666 ? C2 C1 C6 O1 -1.7(5) . . . . ? C5 C1 C6 O1 178.0(3) . . . . ? C2 C1 C6 N1 179.4(3) . . . . ? C5 C1 C6 N1 -0.9(4) . . . . ? C3 C4 C7 O2 -4.6(5) . . . . ? C5 C4 C7 O2 176.2(3) . . . . ? C3 C4 C7 N1 175.9(3) . . . . ? C5 C4 C7 N1 -3.3(5) . . . . ? N1 C8 C9 C10 63.4(5) . . . . ? C8 C9 C10 C11 178.0(5) . . . . ? C9 C10 C11 C12' 165.6(12) . . . . ? C9 C10 C11 C12 -169.1(14) . . . . ? C10 C11 C12 C13 165.1(15) . . . . ? C12' C11 C12 C13 -74(4) . . . . ? C10 C11 C12' C13' 80(2) . . . . ? C12 C11 C12' C13' 9(3) . . . . ? C19 C14 C15 C16 1.9(5) . . . . ? P1 C14 C15 C16 -176.0(3) . . . . ? C14 C15 C16 C17 -1.4(6) . . . . ? C15 C16 C17 O3 -178.5(3) . . . . ? C15 C16 C17 C18 0.3(6) . . . . ? O3 C17 C18 C19 179.0(3) . . . . ? C16 C17 C18 C19 0.3(6) . . . . ? C17 C18 C19 C14 0.2(6) . . . . ? C15 C14 C19 C18 -1.3(5) . . . . ? P1 C14 C19 C18 176.4(3) . . . . ? C27 C21 C22 C24 -3.6(6) . . . . ? P1 C21 C22 C24 -177.2(3) . . . . ? C21 C22 C24 C25 2.7(6) . . . . ? C22 C24 C25 O4 179.1(4) . . . . ? C22 C24 C25 C26 -0.3(6) . . . . ? O4 C25 C26 C27 179.3(4) . . . . ? C24 C25 C26 C27 -1.2(7) . . . . ? C22 C21 C27 C26 2.0(6) . . . . ? P1 C21 C27 C26 175.5(3) . . . . ? C25 C26 C27 C21 0.4(7) . . . . ? C34 C29 C30 C31 -1.1(5) . . . . ? P1 C29 C30 C31 179.5(3) . . . . ? C29 C30 C31 C32 1.6(6) . . . . ? C30 C31 C32 O5 -179.4(3) . . . . ? C30 C31 C32 C33 -1.2(6) . . . . ? O5 C32 C33 C34 178.2(4) . . . . ? C31 C32 C33 C34 0.2(6) . . . . ? C32 C33 C34 C29 0.3(6) . . . . ? C30 C29 C34 C33 0.1(5) . . . . ? P1 C29 C34 C33 179.5(3) . . . . ? C16 C17 O3 C20 176.8(4) . . . . ? C18 C17 O3 C20 -2.0(6) . . . . ? C26 C25 O4 C28 177.5(4) . . . . ? C24 C25 O4 C28 -1.9(7) . . . . ? C31 C32 O5 C35 -177.3(4) . . . . ? C33 C32 O5 C35 4.5(6) . . . . ? C19 C14 P1 C21 19.3(3) . . . . ? C15 C14 P1 C21 -162.9(3) . . . . ? C19 C14 P1 C29 -97.3(3) . . . . ? C15 C14 P1 C29 80.4(3) . . . . ? C19 C14 P1 C2 147.6(3) . . . . ? C15 C14 P1 C2 -34.7(3) . . . . ? C27 C21 P1 C14 127.6(3) . . . . ? C22 C21 P1 C14 -59.0(3) . . . . ? C27 C21 P1 C29 -114.5(3) . . . . ? C22 C21 P1 C29 58.9(3) . . . . ? C27 C21 P1 C2 0.8(4) . . . . ? C22 C21 P1 C2 174.2(3) . . . . ? C34 C29 P1 C14 -10.4(3) . . . . ? C30 C29 P1 C14 169.0(3) . . . . ? C34 C29 P1 C21 -135.4(3) . . . . ? C30 C29 P1 C21 44.0(3) . . . . ? C34 C29 P1 C2 106.0(3) . . . . ? C30 C29 P1 C2 -74.6(3) . . . . ? C1 C2 P1 C14 -62.4(3) . . . . ? C3 C2 P1 C14 116.5(2) 2_666 . . . ? C1 C2 P1 C21 69.0(3) . . . . ? C3 C2 P1 C21 -112.1(2) 2_666 . . . ? C1 C2 P1 C29 -177.3(3) . . . . ? C3 C2 P1 C29 1.6(3) 2_666 . . . ? O1 C6 N1 C7 178.5(3) . . . . ? C1 C6 N1 C7 -2.6(5) . . . . ? O1 C6 N1 C8 -0.6(5) . . . . ? C1 C6 N1 C8 178.3(3) . . . . ? O2 C7 N1 C6 -174.9(3) . . . . ? C4 C7 N1 C6 4.6(5) . . . . ? O2 C7 N1 C8 4.3(5) . . . . ? C4 C7 N1 C8 -176.3(3) . . . . ? C9 C8 N1 C6 -101.7(4) . . . . ? C9 C8 N1 C7 79.1(4) . . . . ? F2' B1' F1' F4' -133(2) . . . . ? F3' B1' F1' F4' 121.4(18) . . . . ? F2' B1' F4' F1' 68(2) . . . . ? F3' B1' F4' F1' -74(2) . . . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 1.000 0.500 99 16 ' '