#------------------------------------------------------------------------------ #$Date: 2020-05-01 01:18:44 +0300 (Fri, 01 May 2020) $ #$Revision: 251335 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/79/1557971.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_1557971 loop_ _publ_author_name 'Zhang, Ruoyao' 'Niu, Guangle' 'Lu, Qing' 'Huang, Xiaolin' 'Chau, Joe H. C.' 'Kwok, Ryan T. K.' 'Yu, Xiaoqiang' 'Li, Min-Hui' 'Lam, Jacky Wing Yip' 'Tang, Ben Zhong' _publ_section_title ; Cancer cell discrimination and dynamic viability monitoring through wash-free bioimaging by AIEgens ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D0SC01213K _journal_year 2020 _chemical_formula_sum 'C17 H17 F6 N2 P' _chemical_formula_weight 394.29 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2020-02-26 deposited with the CCDC. 2020-04-30 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.373(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.8004(9) _cell_length_b 11.9948(15) _cell_length_c 21.500(3) _cell_measurement_reflns_used 9590 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 74.57 _cell_measurement_theta_min 4.13 _cell_volume 1746.0(4) _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-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 150(2) _diffrn_detector_area_resol_mean 8.3 _diffrn_measured_fraction_theta_full 0.974 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0668 _diffrn_reflns_av_unetI/netI 0.0440 _diffrn_reflns_Laue_measured_fraction_full 0.974 _diffrn_reflns_Laue_measured_fraction_max 0.973 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 24274 _diffrn_reflns_point_group_measured_fraction_full 0.974 _diffrn_reflns_point_group_measured_fraction_max 0.973 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 74.619 _diffrn_reflns_theta_min 4.131 _exptl_absorpt_coefficient_mu 2.005 _exptl_absorpt_correction_T_max 0.585 _exptl_absorpt_correction_T_min 0.501 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'APEX2 Software Suite (Bruker, 2005)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.500 _exptl_crystal_description block _exptl_crystal_F_000 808 _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.300 _refine_diff_density_max 0.883 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.077 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 236 _refine_ls_number_reflns 3487 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0876 _refine_ls_R_factor_gt 0.0851 _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^)+(0.1159P)^2^+3.0033P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2292 _refine_ls_wR_factor_ref 0.2315 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3291 _reflns_number_total 3487 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc01213k2.cif _cod_data_source_block ZRY01-sad _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1557971 _shelx_shelxl_version_number 2014/7 _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 0.501 _shelx_estimated_absorpt_t_max 0.584 _exptl_absorpt_special_details ; about 2 hours for data collection, with scale. ; _shelx_res_file ; ZRY01-sad.res created by SHELXL-2014/7 TITL ZRY01-sad_a.res in P2(1)/n CELL 1.54178 6.8004 11.9948 21.4995 90.000 95.373 90.000 ZERR 4.00 0.0009 0.0015 0.0027 0.000 0.004 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H N F P UNIT 68 68 8 24 4 REM REM E:\struc-2018\ZRY01\work\autostructure_private\ZRY01-sad_a.hkl REM L.S. 20 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.300 0.320 0.400 HTAB CONF TEMP -123.150 WGHT 0.115900 3.003300 FVAR 1.51465 P1 5 0.646613 0.268556 0.170435 11.00000 0.07127 0.03942 = 0.03026 -0.00778 -0.00269 0.00703 F1 4 0.537578 0.166663 0.135381 11.00000 0.07986 0.05403 = 0.05396 -0.01425 -0.00541 -0.00419 F2 4 0.843229 0.232640 0.142977 11.00000 0.08403 0.10909 = 0.16270 -0.07770 0.03873 -0.02077 F3 4 0.701517 0.189637 0.228945 11.00000 0.19375 0.04645 = 0.06596 0.00181 -0.04543 0.01033 F4 4 0.593980 0.347277 0.113846 11.00000 0.19811 0.07405 = 0.04806 0.01667 -0.03477 -0.03036 F5 4 0.753886 0.370482 0.207387 11.00000 0.11413 0.04425 = 0.05291 -0.01536 -0.01248 -0.00276 F6 4 0.456264 0.302716 0.201501 11.00000 0.10994 0.06422 = 0.14051 -0.02281 0.05811 0.01213 N1 3 0.874163 0.824856 0.646518 11.00000 0.03085 0.02849 = 0.04720 -0.00736 0.00646 -0.00325 N2 3 0.651929 0.336523 0.345473 11.00000 0.03760 0.04812 = 0.03134 -0.00473 0.00511 -0.00111 AFIX 43 H2 2 0.632766 0.321507 0.305298 11.00000 -1.20000 AFIX 0 C1 1 0.761995 0.954431 0.724844 11.00000 0.09418 0.11518 = 0.14378 -0.10299 0.07409 -0.06397 AFIX 137 H1C 2 0.644070 0.975694 0.697731 11.00000 -1.50000 H1B 2 0.805188 1.017479 0.751726 11.00000 -1.50000 H1A 2 0.730911 0.890839 0.750817 11.00000 -1.50000 AFIX 0 C2 1 0.917177 0.924046 0.687095 11.00000 0.05139 0.04047 = 0.07875 -0.02692 0.00820 -0.00922 AFIX 23 H2A 2 1.038590 0.909218 0.714982 11.00000 -1.20000 H2B 2 0.944398 0.988295 0.660298 11.00000 -1.20000 AFIX 0 C3 1 0.878817 0.720879 0.670819 11.00000 0.04143 0.03498 = 0.03478 -0.00227 0.00627 -0.00227 AFIX 43 H3 2 0.904099 0.711467 0.714713 11.00000 -1.20000 AFIX 0 C4 1 0.848143 0.629590 0.633858 11.00000 0.04072 0.03032 = 0.04630 -0.00486 0.01066 -0.00651 AFIX 43 H4 2 0.854537 0.557697 0.652477 11.00000 -1.20000 AFIX 0 C5 1 0.807978 0.638508 0.570039 11.00000 0.02443 0.04040 = 0.04421 -0.00682 0.00761 0.00056 C8 1 0.776286 0.535260 0.533337 11.00000 0.03348 0.03424 = 0.04459 0.00736 0.00844 0.00271 AFIX 43 H8 2 0.789861 0.466282 0.555028 11.00000 -1.20000 AFIX 0 C9 1 0.730345 0.532189 0.472400 11.00000 0.03166 0.03525 = 0.04428 -0.00479 0.00826 0.00073 AFIX 43 H9 2 0.715888 0.601759 0.451349 11.00000 -1.20000 AFIX 0 C11 1 0.700028 0.433252 0.434763 11.00000 0.02708 0.03134 = 0.04161 -0.00508 0.00683 0.00014 C12 1 0.695356 0.315388 0.450178 11.00000 0.02375 0.03464 = 0.03377 -0.00495 0.00345 0.00188 C13 1 0.710559 0.254177 0.505314 11.00000 0.03939 0.03872 = 0.03762 0.00096 -0.00025 0.00294 AFIX 43 H13 2 0.729314 0.290530 0.544680 11.00000 -1.20000 AFIX 0 C14 1 0.697760 0.138735 0.501657 11.00000 0.05220 0.03909 = 0.05820 0.01125 0.00258 0.00247 AFIX 43 H14 2 0.706183 0.096314 0.539127 11.00000 -1.20000 AFIX 0 C15 1 0.672969 0.083797 0.444622 11.00000 0.04002 0.02928 = 0.08728 -0.00400 0.00890 0.00041 AFIX 43 H15 2 0.667551 0.004661 0.443898 11.00000 -1.20000 AFIX 0 C10 1 0.672117 0.440072 0.370637 11.00000 0.03864 0.03926 = 0.04069 0.00237 0.00915 0.00110 AFIX 43 H10 2 0.667640 0.507508 0.347374 11.00000 -1.20000 AFIX 0 C17 1 0.666187 0.258476 0.392815 11.00000 0.02440 0.03660 = 0.03716 -0.00741 0.00236 -0.00034 C16 1 0.655967 0.142109 0.388719 11.00000 0.03039 0.03816 = 0.06113 -0.01998 0.00764 -0.00344 AFIX 43 H16 2 0.638259 0.104957 0.349571 11.00000 -1.20000 AFIX 0 C6 1 0.803273 0.746156 0.544925 11.00000 0.02871 0.05661 = 0.03467 -0.00249 0.00318 0.00505 AFIX 43 H6 2 0.776412 0.756589 0.501152 11.00000 -1.20000 AFIX 0 C7 1 0.837636 0.837328 0.583691 11.00000 0.03203 0.03574 = 0.05513 0.01157 0.00884 0.00649 AFIX 43 H7 2 0.835689 0.910023 0.566105 11.00000 -1.20000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM ZRY01-sad_a.res in P2(1)/n REM R1 = 0.0851 for 3291 Fo > 4sig(Fo) and 0.0876 for all 3487 data REM 236 parameters refined using 0 restraints END WGHT 0.0998 3.0500 REM Instructions for potential hydrogen bonds HTAB N2 F3 HTAB N2 F5 HTAB N2 F6 EQIV $1 -x+2, -y+1, -z+1 HTAB C2 F3_$1 EQIV $2 x+1/2, -y+3/2, z+1/2 HTAB C2 F4_$2 REM Highest difference peak 0.883, deepest hole -0.534, 1-sigma level 0.077 Q1 1 0.7631 0.6069 0.4997 11.00000 0.05 0.88 Q2 1 0.7416 0.4835 0.5027 11.00000 0.05 0.64 Q3 1 0.7891 0.2061 0.1949 11.00000 0.05 0.61 Q4 1 0.4633 0.3431 0.1406 11.00000 0.05 0.59 Q5 1 0.7494 0.2801 0.1174 11.00000 0.05 0.58 Q6 1 0.5308 0.2406 0.2248 11.00000 0.05 0.50 Q7 1 0.7811 0.6440 0.6043 11.00000 0.05 0.39 Q8 1 0.7031 0.3817 0.1401 11.00000 0.05 0.37 Q9 1 0.9112 0.8853 0.7208 11.00000 0.05 0.36 Q10 1 0.8477 0.8048 0.5482 11.00000 0.05 0.34 Q11 1 0.7767 0.3634 0.1581 11.00000 0.05 0.34 Q12 1 0.7181 0.2941 0.4257 11.00000 0.05 0.29 Q13 1 0.5303 0.3291 0.2051 11.00000 0.05 0.28 Q14 1 0.5388 0.1740 0.1813 11.00000 0.05 0.26 Q15 1 0.6412 0.9157 0.7300 11.00000 0.05 0.25 Q16 1 0.5941 0.3464 0.0991 11.00000 0.05 0.24 Q17 1 0.7065 0.1445 0.1528 11.00000 0.05 0.24 Q18 1 0.7361 0.4423 0.4043 11.00000 0.05 0.23 Q19 1 0.8873 0.8830 0.5980 11.00000 0.05 0.23 Q20 1 0.5761 0.3828 0.1717 11.00000 0.05 0.23 ; _shelx_res_checksum 13930 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' 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 0.64661(15) 0.26856(8) 0.17043(4) 0.0475(3) Uani 1 1 d . . . . . F1 F 0.5376(4) 0.1667(2) 0.13538(11) 0.0634(7) Uani 1 1 d . . . . . F2 F 0.8432(5) 0.2326(3) 0.1430(2) 0.1169(15) Uani 1 1 d . . . . . F3 F 0.7015(7) 0.1896(2) 0.22895(14) 0.1057(14) Uani 1 1 d . . . . . F4 F 0.5940(7) 0.3473(3) 0.11385(13) 0.1097(14) Uani 1 1 d . . . . . F5 F 0.7539(5) 0.3705(2) 0.20739(11) 0.0717(8) Uani 1 1 d . . . . . F6 F 0.4563(5) 0.3027(3) 0.20150(19) 0.1020(12) Uani 1 1 d . . . . . N1 N 0.8742(4) 0.8249(2) 0.64652(13) 0.0353(6) Uani 1 1 d . . . . . N2 N 0.6519(4) 0.3365(2) 0.34547(12) 0.0389(6) Uani 1 1 d . . . . . H2 H 0.6328 0.3215 0.3053 0.047 Uiso 1 1 calc R U . . . C1 C 0.7620(9) 0.9544(5) 0.7248(3) 0.114(3) Uani 1 1 d . . . . . H1C H 0.6441 0.9757 0.6977 0.171 Uiso 1 1 calc R U . . . H1B H 0.8052 1.0175 0.7517 0.171 Uiso 1 1 calc R U . . . H1A H 0.7309 0.8908 0.7508 0.171 Uiso 1 1 calc R U . . . C2 C 0.9172(6) 0.9240(3) 0.6871(2) 0.0567(10) Uani 1 1 d . . . . . H2A H 1.0386 0.9092 0.7150 0.068 Uiso 1 1 calc R U . . . H2B H 0.9444 0.9883 0.6603 0.068 Uiso 1 1 calc R U . . . C3 C 0.8788(5) 0.7209(3) 0.67082(15) 0.0369(7) Uani 1 1 d . . . . . H3 H 0.9041 0.7115 0.7147 0.044 Uiso 1 1 calc R U . . . C4 C 0.8481(5) 0.6296(3) 0.63386(15) 0.0387(7) Uani 1 1 d . . . . . H4 H 0.8545 0.5577 0.6525 0.046 Uiso 1 1 calc R U . . . C5 C 0.8080(4) 0.6385(3) 0.57004(15) 0.0361(7) Uani 1 1 d . . . . . C8 C 0.7763(4) 0.5353(3) 0.53334(15) 0.0371(7) Uani 1 1 d . . . . . H8 H 0.7899 0.4663 0.5550 0.045 Uiso 1 1 calc R U . . . C9 C 0.7303(4) 0.5322(3) 0.47240(15) 0.0368(7) Uani 1 1 d . . . . . H9 H 0.7159 0.6018 0.4513 0.044 Uiso 1 1 calc R U . . . C11 C 0.7000(4) 0.4333(2) 0.43476(14) 0.0331(6) Uani 1 1 d . . . . . C12 C 0.6954(4) 0.3154(2) 0.45018(13) 0.0307(6) Uani 1 1 d . . . . . C13 C 0.7106(5) 0.2542(3) 0.50531(15) 0.0388(7) Uani 1 1 d . . . . . H13 H 0.7293 0.2905 0.5447 0.047 Uiso 1 1 calc R U . . . C14 C 0.6978(6) 0.1387(3) 0.50166(19) 0.0500(9) Uani 1 1 d . . . . . H14 H 0.7062 0.0963 0.5391 0.060 Uiso 1 1 calc R U . . . C15 C 0.6730(5) 0.0838(3) 0.4446(2) 0.0520(9) Uani 1 1 d . . . . . H15 H 0.6676 0.0047 0.4439 0.062 Uiso 1 1 calc R U . . . C10 C 0.6721(5) 0.4401(3) 0.37064(15) 0.0392(7) Uani 1 1 d . . . . . H10 H 0.6676 0.5075 0.3474 0.047 Uiso 1 1 calc R U . . . C17 C 0.6662(4) 0.2585(3) 0.39282(14) 0.0328(6) Uani 1 1 d . . . . . C16 C 0.6560(4) 0.1421(3) 0.38872(18) 0.0430(8) Uani 1 1 d . . . . . H16 H 0.6383 0.1050 0.3496 0.052 Uiso 1 1 calc R U . . . C6 C 0.8033(4) 0.7462(3) 0.54492(15) 0.0400(7) Uani 1 1 d . . . . . H6 H 0.7764 0.7566 0.5012 0.048 Uiso 1 1 calc R U . . . C7 C 0.8376(4) 0.8373(3) 0.58369(17) 0.0407(7) Uani 1 1 d . . . . . H7 H 0.8357 0.9100 0.5661 0.049 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 P1 0.0713(7) 0.0394(5) 0.0303(5) -0.0078(3) -0.0027(4) 0.0070(4) F1 0.0799(16) 0.0540(14) 0.0540(13) -0.0143(11) -0.0054(11) -0.0042(12) F2 0.084(2) 0.109(3) 0.163(4) -0.078(3) 0.039(2) -0.0208(19) F3 0.194(4) 0.0465(15) 0.0660(18) 0.0018(13) -0.045(2) 0.0103(19) F4 0.198(4) 0.074(2) 0.0481(15) 0.0167(14) -0.0348(19) -0.030(2) F5 0.114(2) 0.0442(13) 0.0529(13) -0.0154(10) -0.0125(13) -0.0028(13) F6 0.110(3) 0.0642(19) 0.141(3) -0.023(2) 0.058(2) 0.0121(17) N1 0.0308(12) 0.0285(12) 0.0472(15) -0.0074(11) 0.0065(10) -0.0032(9) N2 0.0376(13) 0.0481(16) 0.0313(13) -0.0047(11) 0.0051(10) -0.0011(11) C1 0.094(4) 0.115(5) 0.144(5) -0.103(4) 0.074(4) -0.064(4) C2 0.051(2) 0.0405(19) 0.079(3) -0.0269(19) 0.0082(18) -0.0092(15) C3 0.0414(16) 0.0350(16) 0.0348(15) -0.0023(12) 0.0063(12) -0.0023(12) C4 0.0407(16) 0.0303(15) 0.0463(17) -0.0049(13) 0.0107(13) -0.0065(12) C5 0.0244(12) 0.0404(16) 0.0442(16) -0.0068(13) 0.0076(11) 0.0006(11) C8 0.0335(14) 0.0342(15) 0.0446(16) 0.0074(13) 0.0084(12) 0.0027(12) C9 0.0317(14) 0.0352(15) 0.0443(16) -0.0048(13) 0.0083(12) 0.0007(11) C11 0.0271(13) 0.0313(14) 0.0416(15) -0.0051(12) 0.0068(11) 0.0001(10) C12 0.0237(12) 0.0346(15) 0.0338(14) -0.0050(11) 0.0035(10) 0.0019(10) C13 0.0394(16) 0.0387(16) 0.0376(16) 0.0010(13) -0.0003(12) 0.0029(13) C14 0.0522(19) 0.0391(18) 0.058(2) 0.0113(15) 0.0026(16) 0.0025(15) C15 0.0400(17) 0.0293(16) 0.087(3) -0.0040(17) 0.0089(17) 0.0004(13) C10 0.0386(15) 0.0393(16) 0.0407(16) 0.0024(13) 0.0092(12) 0.0011(12) C17 0.0244(12) 0.0366(15) 0.0372(15) -0.0074(12) 0.0024(11) -0.0003(11) C16 0.0304(14) 0.0382(17) 0.061(2) -0.0200(15) 0.0076(13) -0.0034(12) C6 0.0287(14) 0.057(2) 0.0347(15) -0.0025(14) 0.0032(11) 0.0050(13) C7 0.0320(14) 0.0357(16) 0.0551(19) 0.0116(14) 0.0088(13) 0.0065(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 '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 F4 P1 F6 92.1(2) . . ? F4 P1 F2 90.8(3) . . ? F6 P1 F2 176.8(2) . . ? F4 P1 F1 91.90(15) . . ? F6 P1 F1 92.06(18) . . ? F2 P1 F1 89.23(16) . . ? F4 P1 F3 179.13(17) . . ? F6 P1 F3 87.7(2) . . ? F2 P1 F3 89.4(3) . . ? F1 P1 F3 88.96(15) . . ? F4 P1 F5 89.16(16) . . ? F6 P1 F5 86.84(18) . . ? F2 P1 F5 91.81(17) . . ? F1 P1 F5 178.50(15) . . ? F3 P1 F5 89.98(15) . . ? C3 N1 C7 118.8(3) . . ? C3 N1 C2 121.0(3) . . ? C7 N1 C2 120.2(3) . . ? C10 N2 C17 109.2(3) . . ? C10 N2 H2 125.4 . . ? C17 N2 H2 125.4 . . ? C2 C1 H1C 109.5 . . ? C2 C1 H1B 109.5 . . ? H1C C1 H1B 109.5 . . ? C2 C1 H1A 109.5 . . ? H1C C1 H1A 109.5 . . ? H1B C1 H1A 109.5 . . ? C1 C2 N1 114.8(3) . . ? C1 C2 H2A 108.6 . . ? N1 C2 H2A 108.6 . . ? C1 C2 H2B 108.6 . . ? N1 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? N1 C3 C4 121.4(3) . . ? N1 C3 H3 119.3 . . ? C4 C3 H3 119.3 . . ? C3 C4 C5 121.7(3) . . ? C3 C4 H4 119.1 . . ? C5 C4 H4 119.1 . . ? C4 C5 C6 116.8(3) . . ? C4 C5 C8 118.3(3) . . ? C6 C5 C8 124.9(3) . . ? C9 C8 C5 124.4(3) . . ? C9 C8 H8 117.8 . . ? C5 C8 H8 117.8 . . ? C8 C9 C11 126.1(3) . . ? C8 C9 H9 116.9 . . ? C11 C9 H9 116.9 . . ? C10 C11 C9 120.9(3) . . ? C10 C11 C12 106.4(3) . . ? C9 C11 C12 132.7(3) . . ? C13 C12 C17 119.0(3) . . ? C13 C12 C11 135.0(3) . . ? C17 C12 C11 106.0(3) . . ? C14 C13 C12 118.6(3) . . ? C14 C13 H13 120.7 . . ? C12 C13 H13 120.7 . . ? C15 C14 C13 121.7(3) . . ? C15 C14 H14 119.2 . . ? C13 C14 H14 119.2 . . ? C16 C15 C14 121.3(3) . . ? C16 C15 H15 119.3 . . ? C14 C15 H15 119.3 . . ? N2 C10 C11 110.1(3) . . ? N2 C10 H10 124.9 . . ? C11 C10 H10 124.9 . . ? N2 C17 C16 129.1(3) . . ? N2 C17 C12 108.2(3) . . ? C16 C17 C12 122.7(3) . . ? C15 C16 C17 116.7(3) . . ? C15 C16 H16 121.7 . . ? C17 C16 H16 121.7 . . ? C7 C6 C5 120.1(3) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? N1 C7 C6 121.2(3) . . ? N1 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 F4 1.555(3) . ? P1 F6 1.566(3) . ? P1 F2 1.572(4) . ? P1 F1 1.583(2) . ? P1 F3 1.591(3) . ? P1 F5 1.597(2) . ? N1 C3 1.351(4) . ? N1 C7 1.359(4) . ? N1 C2 1.488(4) . ? N2 C10 1.357(4) . ? N2 C17 1.380(4) . ? N2 H2 0.8800 . ? C1 C2 1.437(6) . ? C1 H1C 0.9800 . ? C1 H1B 0.9800 . ? C1 H1A 0.9800 . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.358(4) . ? C3 H3 0.9500 . ? C4 C5 1.378(5) . ? C4 H4 0.9500 . ? C5 C6 1.399(5) . ? C5 C8 1.473(4) . ? C8 C9 1.319(5) . ? C8 H8 0.9500 . ? C9 C11 1.440(4) . ? C9 H9 0.9500 . ? C11 C10 1.376(4) . ? C11 C12 1.453(4) . ? C12 C13 1.390(4) . ? C12 C17 1.407(4) . ? C13 C14 1.389(5) . ? C13 H13 0.9500 . ? C14 C15 1.388(6) . ? C14 H14 0.9500 . ? C15 C16 1.386(6) . ? C15 H15 0.9500 . ? C10 H10 0.9500 . ? C17 C16 1.400(4) . ? C16 H16 0.9500 . ? C6 C7 1.382(5) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? 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 C3 N1 C2 C1 -74.5(6) . . . . ? C7 N1 C2 C1 108.4(5) . . . . ? C7 N1 C3 C4 0.1(4) . . . . ? C2 N1 C3 C4 -177.1(3) . . . . ? N1 C3 C4 C5 -1.0(5) . . . . ? C3 C4 C5 C6 1.0(4) . . . . ? C3 C4 C5 C8 -179.9(3) . . . . ? C4 C5 C8 C9 177.6(3) . . . . ? C6 C5 C8 C9 -3.3(5) . . . . ? C5 C8 C9 C11 179.4(3) . . . . ? C8 C9 C11 C10 -173.4(3) . . . . ? C8 C9 C11 C12 5.0(5) . . . . ? C10 C11 C12 C13 -178.7(3) . . . . ? C9 C11 C12 C13 2.7(6) . . . . ? C10 C11 C12 C17 0.6(3) . . . . ? C9 C11 C12 C17 -178.0(3) . . . . ? C17 C12 C13 C14 0.5(4) . . . . ? C11 C12 C13 C14 179.6(3) . . . . ? C12 C13 C14 C15 0.9(5) . . . . ? C13 C14 C15 C16 -1.3(5) . . . . ? C17 N2 C10 C11 0.0(3) . . . . ? C9 C11 C10 N2 178.4(3) . . . . ? C12 C11 C10 N2 -0.4(3) . . . . ? C10 N2 C17 C16 -179.4(3) . . . . ? C10 N2 C17 C12 0.4(3) . . . . ? C13 C12 C17 N2 178.8(3) . . . . ? C11 C12 C17 N2 -0.6(3) . . . . ? C13 C12 C17 C16 -1.4(4) . . . . ? C11 C12 C17 C16 179.2(3) . . . . ? C14 C15 C16 C17 0.4(5) . . . . ? N2 C17 C16 C15 -179.3(3) . . . . ? C12 C17 C16 C15 1.0(4) . . . . ? C4 C5 C6 C7 -0.1(4) . . . . ? C8 C5 C6 C7 -179.2(3) . . . . ? C3 N1 C7 C6 0.8(4) . . . . ? C2 N1 C7 C6 178.0(3) . . . . ? C5 C6 C7 N1 -0.8(4) . . . . ?