#------------------------------------------------------------------------------ #$Date: 2019-08-15 03:23:38 +0300 (Thu, 15 Aug 2019) $ #$Revision: 217532 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/22/1552224.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_1552224 loop_ _publ_author_name 'Zhao, Na' 'Li, Yan' 'Yang, Weiyao' 'Zhuang, Jiabao' 'Li, Yue' 'Li, Nan' _publ_section_title ; Multifunctional pyrazoline based AIEgens: real-time tracking and specific protein “fishing” of lipid droplets ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC03111A _journal_year 2019 _chemical_formula_moiety '2(C22 H15 F5 N2 O)' _chemical_formula_sum 'C44 H30 F10 N4 O2' _chemical_formula_weight 836.72 _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' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _audit_creation_date 2019-02-27 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-05-20 deposited with the CCDC. 2019-08-14 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 92.560(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.0842(5) _cell_length_b 6.3205(2) _cell_length_c 42.4385(15) _cell_measurement_reflns_used 7990 _cell_measurement_temperature 298 _cell_measurement_theta_max 71.3570 _cell_measurement_theta_min 3.8250 _cell_volume 3774.1(2) _computing_cell_refinement 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXS (Sheldrick, 2008)' _diffrn_ambient_temperature 298 _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.0356 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -30.00 65.00 1.00 6.91 -- 37.91 -77.00-150.00 95 2 \w 21.00 105.00 1.00 6.91 -- 37.91 57.00 -60.00 84 3 \w -30.00 65.00 1.00 6.91 -- 37.91 -77.00 -90.00 95 4 \w -31.00 57.00 1.00 6.91 -- 37.91 -37.00 -60.00 88 5 \w -29.00 55.00 1.00 6.91 -- 37.91 -57.00-150.00 84 6 \w -30.00 65.00 1.00 6.91 -- 37.91 -77.00 0.00 95 7 \w 91.00 176.00 1.00 27.65 -- 108.00 45.00 -60.00 85 8 \w 39.00 109.00 1.00 27.65 -- 108.00 -94.00 120.00 70 9 \w 38.00 129.00 1.00 27.65 -- 108.00 -30.00-150.00 91 10 \w 41.00 126.00 1.00 27.65 -- 108.00 -61.00 30.00 85 11 \w 38.00 129.00 1.00 27.65 -- 108.00 -30.00 120.00 91 12 \w 100.00 178.00 1.00 27.65 -- 108.00 111.00-120.00 78 13 \w 38.00 116.00 1.00 27.65 -- 108.00-111.00-150.00 78 14 \w 39.00 109.00 1.00 27.65 -- 108.00 -94.00-120.00 70 15 \w 11.00 105.00 1.00 6.91 -- 37.91 77.00-180.00 94 16 \w 21.00 105.00 1.00 6.91 -- 37.91 57.00 120.00 84 17 \w 11.00 105.00 1.00 6.91 -- 37.91 77.00 30.00 94 18 \w 21.00 105.00 1.00 6.91 -- 37.91 57.00 0.00 84 19 \w 11.00 105.00 1.00 6.91 -- 37.91 77.00-150.00 94 20 \w -30.00 65.00 1.00 6.91 -- 37.91 -77.00 90.00 95 21 \w 90.00 175.00 1.00 27.65 -- 108.00 61.00-180.00 85 22 \w 91.00 176.00 1.00 27.65 -- 108.00 45.00-120.00 85 23 \w 39.00 109.00 1.00 27.65 -- 108.00 -94.00 0.00 70 24 \w 70.00 178.00 1.00 27.65 -- 108.00 15.00 150.00 108 25 \w 70.00 178.00 1.00 27.65 -- 108.00 15.00 60.00 108 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.1040722000 _diffrn_orient_matrix_UB_12 0.0243403000 _diffrn_orient_matrix_UB_13 0.0122212000 _diffrn_orient_matrix_UB_21 0.0315333000 _diffrn_orient_matrix_UB_22 0.0175284000 _diffrn_orient_matrix_UB_23 -0.0341855000 _diffrn_orient_matrix_UB_31 -0.0126845000 _diffrn_orient_matrix_UB_32 0.2419934000 _diffrn_orient_matrix_UB_33 0.0012389000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_unetI/netI 0.0186 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 51 _diffrn_reflns_limit_l_min -52 _diffrn_reflns_number 35658 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 71.945 _diffrn_reflns_theta_min 3.692 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 1.087 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.69981 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.473 _exptl_crystal_description block _exptl_crystal_F_000 1712 _refine_diff_density_max 0.158 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.040 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 543 _refine_ls_number_reflns 7320 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.012 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0503 _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^)+(0.0617P)^2^+1.0971P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1268 _refine_ls_wR_factor_ref 0.1410 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5491 _reflns_number_total 7320 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL exp_15643 in P21/c #14 exp_15643.res created by SHELXL-2018/3 at 10:53:50 on 27-Feb-2019 REM reset to P21/c #14 CELL 1.54184 14.08417 6.32046 42.43851 90 92.5604 90 ZERR 4 0.00048 0.00021 0.00149 0 0.0031 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F N O UNIT 176 120 40 16 8 L.S. 10 PLAN 5 TEMP 24.85 BOND fmap 2 acta REM REM REM WGHT 0.061700 1.097100 FVAR 2.17334 F1 3 0.431878 0.778432 0.236675 11.00000 0.07082 0.08254 = 0.09661 0.02688 0.00557 0.01078 N2 4 0.392805 1.407721 0.175157 11.00000 0.04989 0.05748 = 0.07074 0.00806 0.00951 0.00506 C3 1 0.277992 1.680310 0.159889 11.00000 0.04646 0.05845 = 0.06379 -0.00320 0.00144 -0.00047 AFIX 43 H3 2 0.239508 1.638224 0.175996 11.00000 -1.20000 AFIX 0 C5 1 0.361379 1.570859 0.154929 11.00000 0.04621 0.05074 = 0.05926 -0.00150 -0.00217 -0.00121 C6 1 0.301447 1.004790 0.224197 11.00000 0.05476 0.06371 = 0.05013 -0.00211 0.00007 -0.00578 F7 3 0.160139 1.203607 0.215667 11.00000 0.06372 0.11205 = 0.10559 0.03106 0.01544 0.01955 N8 4 0.327537 1.320312 0.194379 11.00000 0.05299 0.06320 = 0.06371 0.00481 0.00874 0.00230 O9 5 0.289360 2.085623 0.097494 11.00000 0.09298 0.08217 = 0.08244 0.01834 -0.00219 0.02565 F10 3 0.327891 0.511487 0.267988 11.00000 0.11268 0.08682 = 0.10042 0.03589 -0.00693 -0.01332 C11 1 0.339480 0.823663 0.238540 11.00000 0.06220 0.06773 = 0.05955 0.00386 -0.00082 -0.00587 C12 1 0.566053 1.342227 0.167758 11.00000 0.04887 0.05296 = 0.05729 0.00200 0.00375 -0.00036 C13 1 0.357563 1.138142 0.203857 11.00000 0.05326 0.05359 = 0.05738 -0.00193 -0.00100 -0.00176 C15 1 0.593305 1.520428 0.184216 11.00000 0.06036 0.06054 = 0.08043 -0.00913 0.00019 0.00348 AFIX 43 H15 2 0.549245 1.592866 0.195829 11.00000 -1.20000 AFIX 0 C17 1 0.251426 1.851128 0.141180 11.00000 0.05130 0.06253 = 0.06928 -0.00840 -0.00680 0.00945 AFIX 43 H17 2 0.195752 1.924087 0.144985 11.00000 -1.20000 AFIX 0 C19 1 0.306936 1.914263 0.116882 11.00000 0.06160 0.05925 = 0.06229 0.00163 -0.01034 0.00431 F21 3 0.059181 0.937148 0.248318 11.00000 0.06495 0.16325 = 0.10584 0.02059 0.02122 -0.00860 F22 3 0.140300 0.587754 0.275142 11.00000 0.10604 0.14242 = 0.10203 0.03897 0.00924 -0.04770 C24 1 0.415002 1.631412 0.129609 11.00000 0.05239 0.06347 = 0.06488 0.00174 0.00433 0.00803 AFIX 43 H24 2 0.469618 1.556135 0.125256 11.00000 -1.20000 AFIX 0 C27 1 0.466233 1.254297 0.166842 11.00000 0.05001 0.05255 = 0.06101 -0.00357 0.00154 0.00178 AFIX 13 H27 2 0.450639 1.197843 0.145735 11.00000 -1.20000 AFIX 0 C29 1 0.388016 1.801666 0.110931 11.00000 0.06030 0.07236 = 0.06179 0.00636 0.00349 0.00240 AFIX 43 H29 2 0.424773 1.840711 0.094216 11.00000 -1.20000 AFIX 0 C30 1 0.205208 1.037340 0.228641 11.00000 0.06136 0.08047 = 0.05855 0.00506 0.00145 -0.00075 C33 1 0.286504 0.684036 0.255196 11.00000 0.08547 0.07079 = 0.06262 0.01068 -0.00971 -0.01384 C38 1 0.151586 0.899941 0.245556 11.00000 0.05888 0.11120 = 0.06398 0.00163 0.00677 -0.01416 C39 1 0.452247 1.079763 0.191370 11.00000 0.05044 0.05196 = 0.08022 0.00326 0.00280 -0.00108 AFIX 23 H39A 2 0.450423 0.940763 0.181674 11.00000 -1.20000 H39B 2 0.502083 1.082900 0.207896 11.00000 -1.20000 AFIX 0 C43 1 0.686087 1.593507 0.183680 11.00000 0.07630 0.07054 = 0.09762 -0.00698 -0.01128 -0.01699 AFIX 43 H43 2 0.703912 1.715482 0.194682 11.00000 -1.20000 AFIX 0 C49 1 0.633241 1.235853 0.151472 11.00000 0.06442 0.08560 = 0.08960 -0.02555 0.01624 -0.00523 AFIX 43 H49 2 0.616121 1.113683 0.140404 11.00000 -1.20000 AFIX 0 C50 1 0.192153 0.721876 0.258846 11.00000 0.07807 0.09970 = 0.06221 0.01323 0.00013 -0.03150 C51 1 0.214455 2.221655 0.105004 11.00000 0.09290 0.07058 = 0.09894 0.00075 -0.02309 0.02321 AFIX 137 H51A 2 0.215019 2.344274 0.091664 11.00000 -1.50000 H51B 2 0.222321 2.264502 0.126666 11.00000 -1.50000 H51C 2 0.154970 2.148907 0.101802 11.00000 -1.50000 AFIX 0 C55 1 0.751404 1.485584 0.166905 11.00000 0.05605 0.11098 = 0.10091 0.00430 0.00606 -0.01928 AFIX 43 H55 2 0.813488 1.534995 0.166276 11.00000 -1.20000 AFIX 0 C59 1 0.725280 1.306901 0.151260 11.00000 0.06201 0.12859 = 0.11064 -0.02298 0.03053 -0.00330 AFIX 43 H59 2 0.769977 1.231732 0.140291 11.00000 -1.20000 AFIX 0 F4 3 0.053348 0.279672 0.012265 11.00000 0.10803 0.07424 = 0.08005 0.00833 0.00721 0.00992 N14 4 -0.010578 0.005341 0.053168 11.00000 0.07182 0.06852 = 0.06581 0.00864 -0.00456 -0.00225 C16 1 0.065630 -0.102561 0.049289 11.00000 0.08070 0.06429 = 0.05209 -0.00548 -0.00625 0.00462 C18 1 -0.196882 0.141762 0.059242 11.00000 0.06976 0.06843 = 0.06264 0.00724 0.00013 -0.00351 AFIX 43 H18 2 -0.153893 0.231255 0.049907 11.00000 -1.20000 AFIX 0 C20 1 0.143440 -0.014702 0.031754 11.00000 0.08006 0.07463 = 0.04883 -0.01095 -0.00344 0.00195 N23 4 -0.069502 -0.106241 0.071561 11.00000 0.07866 0.07127 = 0.08442 0.02254 0.00445 0.00632 C25 1 -0.021475 -0.345375 0.115979 11.00000 0.05901 0.05763 = 0.06827 0.00469 0.00057 -0.00433 F26 3 0.247496 -0.296051 0.046115 11.00000 0.09756 0.11150 = 0.08918 0.00663 -0.00171 0.02935 C28 1 -0.165187 -0.047841 0.072284 11.00000 0.07677 0.06583 = 0.05860 0.00356 -0.00362 -0.00456 C31 1 0.232685 -0.108946 0.031460 11.00000 0.09049 0.09179 = 0.05571 -0.00536 -0.00821 0.01448 O32 5 -0.450352 0.111569 0.075638 11.00000 0.07028 0.12423 = 0.10762 0.01828 0.00795 -0.00839 C34 1 0.136055 0.175693 0.015133 11.00000 0.09040 0.07536 = 0.05305 -0.00643 -0.00455 0.00104 F35 3 0.199605 0.449723 -0.014559 11.00000 0.14989 0.10268 = 0.08989 0.01982 0.01767 -0.01784 C36 1 -0.355666 0.068317 0.073717 11.00000 0.06780 0.09216 = 0.06896 0.00106 -0.00013 -0.00836 C37 1 -0.031680 -0.314848 0.080629 11.00000 0.09442 0.05347 = 0.07178 0.00288 -0.00627 0.00112 AFIX 13 H37 2 -0.071961 -0.426432 0.071159 11.00000 -1.20000 AFIX 0 C40 1 0.211409 0.266218 0.000786 11.00000 0.10478 0.09674 = 0.05735 -0.00313 0.00254 -0.01054 C41 1 -0.323994 -0.120113 0.086994 11.00000 0.08726 0.08747 = 0.07538 0.00827 0.00227 -0.02435 AFIX 43 H41 2 -0.366970 -0.209160 0.096423 11.00000 -1.20000 AFIX 0 C42 1 -0.230282 -0.177657 0.086474 11.00000 0.08586 0.07259 = 0.07888 0.01289 -0.00406 -0.00866 AFIX 43 H42 2 -0.210188 -0.304427 0.095681 11.00000 -1.20000 AFIX 0 F44 3 0.372678 0.258041 -0.011296 11.00000 0.11009 0.19086 = 0.09421 0.00469 0.02177 -0.03635 C45 1 0.309216 -0.020392 0.017274 11.00000 0.07503 0.14156 = 0.06151 -0.01294 0.00139 0.00576 C46 1 -0.291130 0.199897 0.059879 11.00000 0.07381 0.07647 = 0.07005 0.00757 0.00210 0.00090 AFIX 43 H46 2 -0.311278 0.327641 0.050999 11.00000 -1.20000 AFIX 0 C47 1 0.298516 0.169856 0.002191 11.00000 0.10019 0.12743 = 0.05945 -0.00424 0.00191 -0.01797 F48 3 0.392263 -0.121560 0.018551 11.00000 0.08806 0.19291 = 0.10370 -0.00039 0.00606 0.02504 C52 1 0.016486 -0.418534 0.179498 11.00000 0.06709 0.11971 = 0.07731 0.02568 -0.00457 -0.01007 AFIX 43 H52 2 0.030945 -0.443249 0.200777 11.00000 -1.20000 AFIX 0 C53 1 0.065741 -0.313281 0.065414 11.00000 0.11866 0.06943 = 0.07660 0.00223 0.02253 0.02134 AFIX 23 H53A 2 0.117377 -0.323844 0.081242 11.00000 -1.20000 H53B 2 0.070804 -0.427986 0.050397 11.00000 -1.20000 AFIX 0 C54 1 -0.023307 -0.180891 0.137008 11.00000 0.08874 0.06382 = 0.08162 -0.00098 -0.00222 -0.01139 AFIX 43 H54 2 -0.037002 -0.044613 0.129900 11.00000 -1.20000 AFIX 0 C56 1 -0.003199 -0.545905 0.127401 11.00000 0.08481 0.06570 = 0.08540 0.01365 0.00482 0.00957 AFIX 43 H56 2 -0.004118 -0.659824 0.113520 11.00000 -1.20000 AFIX 0 C57 1 0.016303 -0.580070 0.158882 11.00000 0.09941 0.09084 = 0.09268 0.03117 -0.00190 0.00989 AFIX 43 H57 2 0.029555 -0.716347 0.166078 11.00000 -1.20000 AFIX 0 C58 1 -0.486257 0.298481 0.061333 11.00000 0.07551 0.12762 = 0.10843 -0.00094 0.00800 0.01068 AFIX 137 H58A 2 -0.475236 0.295323 0.039178 11.00000 -1.50000 H58B 2 -0.454675 0.418866 0.070780 11.00000 -1.50000 H58C 2 -0.553278 0.308374 0.064313 11.00000 -1.50000 AFIX 0 C60 1 -0.004460 -0.218554 0.169313 11.00000 0.08221 0.10503 = 0.07721 -0.01648 0.00004 -0.02194 AFIX 43 H60 2 -0.006259 -0.107670 0.183679 11.00000 -1.20000 AFIX 0 HKLF 4 REM exp_15643 in P21/c #14 REM wR2 = 0.1410, GooF = S = 1.012, Restrained GooF = 1.012 for all data REM R1 = 0.0503 for 5491 Fo > 4sig(Fo) and 0.0669 for all 7320 data REM 543 parameters refined using 0 restraints END WGHT 0.0616 1.0970 REM Highest difference peak 0.158, deepest hole -0.195, 1-sigma level 0.040 Q1 1 0.0771 1.1002 0.2613 11.00000 0.05 0.16 Q2 1 0.3669 -0.2827 0.0183 11.00000 0.05 0.15 Q3 1 0.0030 -0.3649 0.0584 11.00000 0.05 0.14 Q4 1 0.0118 -0.2405 0.1246 11.00000 0.05 0.13 Q5 1 -0.1198 -0.1306 0.0589 11.00000 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.0503 for 5491 Fo > 4sig(Fo) and 0.0669 for all 38295 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.16, deepest hole -0.20 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0669 REM R1_gt = 0.0503 REM wR_ref = 0.1410 REM GOOF = 1.012 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 38295 REM Reflections_gt = 5491 REM Parameters = n/a REM Hole = -0.20 REM Peak = 0.16 REM Flack = n/a ; _cod_data_source_file c9sc03111a2.cif _cod_data_source_block exp_15643 _cod_original_cell_volume 3774.0(2) _cod_database_code 1552224 _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. ; _reflns_odcompleteness_completeness 99.92 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C27(H27), C37(H37) 2.b Secondary CH2 refined with riding coordinates: C39(H39A,H39B), C53(H53A,H53B) 2.c Aromatic/amide H refined with riding coordinates: C3(H3), C15(H15), C17(H17), C24(H24), C29(H29), C43(H43), C49(H49), C55(H55), C59(H59), C18(H18), C41(H41), C42(H42), C46(H46), C52(H52), C54(H54), C56(H56), C57(H57), C60(H60) 2.d Idealised Me refined as rotating group: C51(H51A,H51B,H51C), C58(H58A,H58B,H58C) ; _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.384 _oxdiff_exptl_absorpt_empirical_full_min 0.663 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 F1 F 0.43188(9) 0.7784(2) 0.23667(3) 0.0833(4) Uani 1 1 d . N2 N 0.39281(11) 1.4077(3) 0.17516(4) 0.0592(4) Uani 1 1 d . C3 C 0.27799(13) 1.6803(3) 0.15989(5) 0.0563(4) Uani 1 1 d . H3 H 0.239508 1.638224 0.175996 0.068 Uiso 1 1 calc R C5 C 0.36138(12) 1.5709(3) 0.15493(4) 0.0522(4) Uani 1 1 d . C6 C 0.30145(14) 1.0048(3) 0.22420(4) 0.0563(5) Uani 1 1 d . F7 F 0.16014(9) 1.2036(3) 0.21567(4) 0.0934(5) Uani 1 1 d . N8 N 0.32754(11) 1.3203(3) 0.19438(4) 0.0598(4) Uani 1 1 d . O9 O 0.28936(13) 2.0856(3) 0.09749(4) 0.0860(5) Uani 1 1 d . F10 F 0.32789(12) 0.5115(3) 0.26799(4) 0.1003(5) Uani 1 1 d . C11 C 0.33948(15) 0.8237(4) 0.23854(5) 0.0633(5) Uani 1 1 d . C12 C 0.56605(13) 1.3422(3) 0.16776(4) 0.0530(4) Uani 1 1 d . C13 C 0.35756(13) 1.1381(3) 0.20386(4) 0.0548(4) Uani 1 1 d . C15 C 0.59330(15) 1.5204(4) 0.18422(6) 0.0672(5) Uani 1 1 d . H15 H 0.549245 1.592866 0.195829 0.081 Uiso 1 1 calc R C17 C 0.25143(14) 1.8511(3) 0.14118(5) 0.0613(5) Uani 1 1 d . H17 H 0.195752 1.924087 0.144985 0.074 Uiso 1 1 calc R C19 C 0.30694(15) 1.9143(3) 0.11688(5) 0.0614(5) Uani 1 1 d . F21 F 0.05918(10) 0.9371(3) 0.24832(4) 0.1108(6) Uani 1 1 d . F22 F 0.14030(12) 0.5878(3) 0.27514(4) 0.1167(6) Uani 1 1 d . C24 C 0.41500(14) 1.6314(3) 0.12961(5) 0.0602(5) Uani 1 1 d . H24 H 0.469618 1.556135 0.125256 0.072 Uiso 1 1 calc R C27 C 0.46623(13) 1.2543(3) 0.16684(5) 0.0546(4) Uani 1 1 d . H27 H 0.450639 1.197843 0.145735 0.065 Uiso 1 1 calc R C29 C 0.38802(15) 1.8017(4) 0.11093(5) 0.0648(5) Uani 1 1 d . H29 H 0.424773 1.840711 0.094216 0.078 Uiso 1 1 calc R C30 C 0.20521(15) 1.0373(4) 0.22864(5) 0.0668(5) Uani 1 1 d . C33 C 0.28650(18) 0.6840(4) 0.25520(5) 0.0734(6) Uani 1 1 d . C38 C 0.15159(16) 0.8999(5) 0.24556(5) 0.0779(7) Uani 1 1 d . C39 C 0.45225(13) 1.0798(3) 0.19137(5) 0.0609(5) Uani 1 1 d . H39A H 0.450423 0.940763 0.181674 0.073 Uiso 1 1 calc R H39B H 0.502083 1.082900 0.207896 0.073 Uiso 1 1 calc R C43 C 0.68609(18) 1.5935(4) 0.18368(6) 0.0819(7) Uani 1 1 d . H43 H 0.703912 1.715482 0.194682 0.098 Uiso 1 1 calc R C49 C 0.63324(16) 1.2359(4) 0.15147(6) 0.0795(7) Uani 1 1 d . H49 H 0.616121 1.113683 0.140404 0.095 Uiso 1 1 calc R C50 C 0.19215(18) 0.7219(5) 0.25885(5) 0.0801(7) Uani 1 1 d . C51 C 0.21445(19) 2.2217(4) 0.10500(7) 0.0883(8) Uani 1 1 d . H51A H 0.215019 2.344274 0.091664 0.132 Uiso 1 1 calc GR H51B H 0.222321 2.264502 0.126666 0.132 Uiso 1 1 calc GR H51C H 0.154970 2.148907 0.101802 0.132 Uiso 1 1 calc GR C55 C 0.75140(18) 1.4856(5) 0.16691(7) 0.0892(8) Uani 1 1 d . H55 H 0.813488 1.534995 0.166276 0.107 Uiso 1 1 calc R C59 C 0.72528(18) 1.3069(6) 0.15126(7) 0.0996(9) Uani 1 1 d . H59 H 0.769977 1.231732 0.140291 0.120 Uiso 1 1 calc R F4 F 0.05335(11) 0.2797(2) 0.01227(3) 0.0874(4) Uani 1 1 d . N14 N -0.01058(14) 0.0053(3) 0.05317(4) 0.0689(5) Uani 1 1 d . C16 C 0.06563(17) -0.1026(4) 0.04929(5) 0.0660(5) Uani 1 1 d . C18 C -0.19688(16) 0.1418(4) 0.05924(5) 0.0670(5) Uani 1 1 d . H18 H -0.153893 0.231255 0.049907 0.080 Uiso 1 1 calc R C20 C 0.14344(17) -0.0147(4) 0.03175(5) 0.0680(6) Uani 1 1 d . N23 N -0.06950(15) -0.1062(3) 0.07156(5) 0.0781(5) Uani 1 1 d . C25 C -0.02148(15) -0.3454(3) 0.11598(5) 0.0617(5) Uani 1 1 d . F26 F 0.24750(11) -0.2961(3) 0.04612(4) 0.0996(5) Uani 1 1 d . C28 C -0.16519(17) -0.0478(4) 0.07228(5) 0.0673(5) Uani 1 1 d . C31 C 0.23268(19) -0.1089(5) 0.03146(5) 0.0797(7) Uani 1 1 d . O32 O -0.45035(13) 0.1116(4) 0.07564(5) 0.1006(6) Uani 1 1 d . C34 C 0.13605(19) 0.1757(4) 0.01513(5) 0.0732(6) Uani 1 1 d . F35 F 0.19960(15) 0.4497(3) -0.01456(4) 0.1138(6) Uani 1 1 d . C36 C -0.35567(17) 0.0683(4) 0.07372(6) 0.0764(6) Uani 1 1 d . C37 C -0.03168(19) -0.3148(4) 0.08063(5) 0.0735(6) Uani 1 1 d . H37 H -0.071961 -0.426432 0.071159 0.088 Uiso 1 1 calc R C40 C 0.2114(2) 0.2662(5) 0.00079(6) 0.0863(7) Uani 1 1 d . C41 C -0.32399(19) -0.1201(4) 0.08699(6) 0.0834(7) Uani 1 1 d . H41 H -0.366970 -0.209160 0.096423 0.100 Uiso 1 1 calc R C42 C -0.23028(19) -0.1777(4) 0.08647(6) 0.0793(7) Uani 1 1 d . H42 H -0.210188 -0.304427 0.095681 0.095 Uiso 1 1 calc R F44 F 0.37268(14) 0.2580(4) -0.01130(4) 0.1312(7) Uani 1 1 d . C45 C 0.30922(19) -0.0204(6) 0.01727(6) 0.0927(9) Uani 1 1 d . C46 C -0.29113(17) 0.1999(4) 0.05988(5) 0.0735(6) Uani 1 1 d . H46 H -0.311278 0.327641 0.050999 0.088 Uiso 1 1 calc R C47 C 0.2985(2) 0.1699(6) 0.00219(6) 0.0957(9) Uani 1 1 d . F48 F 0.39226(13) -0.1216(4) 0.01855(4) 0.1282(7) Uani 1 1 d . C52 C 0.01649(18) -0.4185(5) 0.17950(7) 0.0883(8) Uani 1 1 d . H52 H 0.030945 -0.443249 0.200777 0.106 Uiso 1 1 calc R C53 C 0.0657(2) -0.3133(4) 0.06541(6) 0.0877(8) Uani 1 1 d . H53A H 0.117377 -0.323844 0.081242 0.105 Uiso 1 1 calc R H53B H 0.070804 -0.427986 0.050397 0.105 Uiso 1 1 calc R C54 C -0.02331(18) -0.1809(4) 0.13701(6) 0.0782(6) Uani 1 1 d . H54 H -0.037002 -0.044613 0.129900 0.094 Uiso 1 1 calc R C56 C -0.00320(18) -0.5459(4) 0.12740(6) 0.0786(6) Uani 1 1 d . H56 H -0.004118 -0.659824 0.113520 0.094 Uiso 1 1 calc R C57 C 0.0163(2) -0.5801(5) 0.15888(7) 0.0945(8) Uani 1 1 d . H57 H 0.029555 -0.716347 0.166078 0.113 Uiso 1 1 calc R C58 C -0.4863(2) 0.2985(6) 0.06133(8) 0.1037(9) Uani 1 1 d . H58A H -0.475236 0.295323 0.039178 0.156 Uiso 1 1 calc GR H58B H -0.454675 0.418866 0.070780 0.156 Uiso 1 1 calc GR H58C H -0.553278 0.308374 0.064313 0.156 Uiso 1 1 calc GR C60 C -0.00446(19) -0.2186(5) 0.16931(6) 0.0883(8) Uani 1 1 d . H60 H -0.006259 -0.107670 0.183679 0.106 Uiso 1 1 calc R 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 F1 0.0708(8) 0.0825(9) 0.0966(9) 0.0269(8) 0.0056(7) 0.0108(7) N2 0.0499(8) 0.0575(10) 0.0707(10) 0.0081(8) 0.0095(7) 0.0051(7) C3 0.0465(9) 0.0585(11) 0.0638(11) -0.0032(9) 0.0014(8) -0.0005(9) C5 0.0462(9) 0.0507(10) 0.0593(10) -0.0015(8) -0.0022(8) -0.0012(8) C6 0.0548(10) 0.0637(12) 0.0501(9) -0.0021(9) 0.0001(8) -0.0058(9) F7 0.0637(8) 0.1121(12) 0.1056(11) 0.0311(9) 0.0154(7) 0.0196(8) N8 0.0530(9) 0.0632(10) 0.0637(9) 0.0048(8) 0.0087(7) 0.0023(8) O9 0.0930(12) 0.0822(11) 0.0824(11) 0.0183(9) -0.0022(9) 0.0256(10) F10 0.1127(12) 0.0868(10) 0.1004(11) 0.0359(9) -0.0069(9) -0.0133(9) C11 0.0622(12) 0.0677(13) 0.0595(11) 0.0039(10) -0.0008(9) -0.0059(10) C12 0.0489(9) 0.0530(11) 0.0573(10) 0.0020(8) 0.0037(8) -0.0004(8) C13 0.0533(10) 0.0536(11) 0.0574(10) -0.0019(9) -0.0010(8) -0.0018(9) C15 0.0604(12) 0.0605(12) 0.0804(14) -0.0091(11) 0.0002(10) 0.0035(10) C17 0.0513(10) 0.0625(12) 0.0693(12) -0.0084(10) -0.0068(9) 0.0094(9) C19 0.0616(11) 0.0593(12) 0.0623(11) 0.0016(9) -0.0103(9) 0.0043(10) F21 0.0649(8) 0.1633(17) 0.1058(11) 0.0206(11) 0.0212(8) -0.0086(10) F22 0.1060(12) 0.1424(16) 0.1020(11) 0.0390(11) 0.0092(9) -0.0477(11) C24 0.0524(10) 0.0635(12) 0.0649(11) 0.0017(10) 0.0043(8) 0.0080(9) C27 0.0500(10) 0.0526(11) 0.0610(10) -0.0036(9) 0.0015(8) 0.0018(8) C29 0.0603(11) 0.0724(14) 0.0618(11) 0.0064(10) 0.0035(9) 0.0024(10) C30 0.0614(12) 0.0805(15) 0.0586(11) 0.0051(11) 0.0015(9) -0.0007(11) C33 0.0855(16) 0.0708(14) 0.0626(12) 0.0107(11) -0.0097(11) -0.0138(12) C38 0.0589(12) 0.111(2) 0.0640(12) 0.0016(13) 0.0068(10) -0.0142(13) C39 0.0504(10) 0.0520(11) 0.0802(13) 0.0033(10) 0.0028(9) -0.0011(9) C43 0.0763(15) 0.0705(15) 0.0976(17) -0.0070(13) -0.0113(13) -0.0170(13) C49 0.0644(13) 0.0856(17) 0.0896(16) -0.0255(14) 0.0162(11) -0.0052(12) C50 0.0781(15) 0.0997(19) 0.0622(12) 0.0132(13) 0.0001(11) -0.0315(14) C51 0.0929(18) 0.0706(15) 0.0989(18) 0.0008(14) -0.0231(14) 0.0232(14) C55 0.0561(13) 0.111(2) 0.1009(19) 0.0043(17) 0.0061(12) -0.0193(14) C59 0.0620(14) 0.129(3) 0.111(2) -0.023(2) 0.0305(14) -0.0033(16) F4 0.1080(11) 0.0742(9) 0.0801(9) 0.0083(7) 0.0072(8) 0.0099(8) N14 0.0718(11) 0.0685(11) 0.0658(10) 0.0086(9) -0.0046(8) -0.0022(10) C16 0.0807(14) 0.0643(13) 0.0521(10) -0.0055(9) -0.0063(10) 0.0046(12) C18 0.0698(13) 0.0684(13) 0.0626(12) 0.0072(10) 0.0001(10) -0.0035(11) C20 0.0801(14) 0.0746(14) 0.0488(10) -0.0110(10) -0.0034(9) 0.0020(12) N23 0.0787(12) 0.0713(12) 0.0844(13) 0.0225(10) 0.0044(10) 0.0063(10) C25 0.0590(11) 0.0576(12) 0.0683(12) 0.0047(10) 0.0006(9) -0.0043(9) F26 0.0976(11) 0.1115(12) 0.0892(10) 0.0066(9) -0.0017(8) 0.0294(9) C28 0.0768(14) 0.0658(13) 0.0586(11) 0.0036(10) -0.0036(10) -0.0046(11) C31 0.0905(17) 0.0918(18) 0.0557(12) -0.0054(12) -0.0082(11) 0.0145(15) O32 0.0703(10) 0.1242(17) 0.1076(14) 0.0183(13) 0.0080(9) -0.0084(11) C34 0.0904(16) 0.0754(15) 0.0530(11) -0.0064(11) -0.0046(11) 0.0010(13) F35 0.1499(16) 0.1027(12) 0.0899(11) 0.0198(10) 0.0177(10) -0.0178(11) C36 0.0678(13) 0.0922(18) 0.0690(13) 0.0011(13) -0.0001(11) -0.0084(13) C37 0.0944(17) 0.0535(12) 0.0718(13) 0.0029(10) -0.0063(12) 0.0011(12) C40 0.105(2) 0.097(2) 0.0573(12) -0.0031(13) 0.0025(13) -0.0105(17) C41 0.0873(17) 0.0875(18) 0.0754(15) 0.0083(13) 0.0023(12) -0.0244(15) C42 0.0859(16) 0.0726(15) 0.0789(15) 0.0129(12) -0.0041(12) -0.0087(13) F44 0.1101(13) 0.191(2) 0.0942(11) 0.0047(13) 0.0218(10) -0.0364(14) C45 0.0750(16) 0.142(3) 0.0615(13) -0.0129(16) 0.0014(12) 0.0058(17) C46 0.0738(14) 0.0765(15) 0.0700(13) 0.0076(12) 0.0021(11) 0.0009(12) C47 0.100(2) 0.127(3) 0.0595(13) -0.0042(16) 0.0019(13) -0.018(2) F48 0.0881(11) 0.193(2) 0.1037(12) -0.0004(13) 0.0061(9) 0.0250(13) C52 0.0671(14) 0.120(2) 0.0773(15) 0.0257(17) -0.0046(12) -0.0101(15) C53 0.119(2) 0.0694(15) 0.0766(15) 0.0022(12) 0.0225(14) 0.0213(15) C54 0.0887(16) 0.0638(14) 0.0816(15) -0.0010(12) -0.0022(12) -0.0114(12) C56 0.0848(16) 0.0657(14) 0.0854(16) 0.0136(12) 0.0048(12) 0.0096(12) C57 0.099(2) 0.091(2) 0.0927(19) 0.0312(17) -0.0019(15) 0.0099(16) C58 0.0755(17) 0.128(3) 0.108(2) -0.001(2) 0.0080(15) 0.0107(18) C60 0.0822(16) 0.105(2) 0.0772(16) -0.0165(15) 0.0000(13) -0.0219(16) 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' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C5 N2 C27 122.97(16) N8 N2 C5 117.32(15) N8 N2 C27 111.95(15) C17 C3 C5 120.78(19) C3 C5 N2 121.37(18) C3 C5 C24 118.13(18) C24 C5 N2 120.48(17) C11 C6 C13 121.61(18) C30 C6 C11 114.84(19) C30 C6 C13 123.34(19) C13 N8 N2 109.09(16) C19 O9 C51 117.5(2) F1 C11 C6 120.39(18) F1 C11 C33 116.5(2) C33 C11 C6 123.1(2) C15 C12 C27 123.67(18) C15 C12 C49 118.4(2) C49 C12 C27 117.95(18) C6 C13 C39 125.29(18) N8 C13 C6 121.46(18) N8 C13 C39 113.23(17) C12 C15 C43 120.5(2) C19 C17 C3 120.48(19) O9 C19 C17 125.6(2) O9 C19 C29 115.2(2) C29 C19 C17 119.28(19) C29 C24 C5 120.80(19) N2 C27 C12 114.49(16) N2 C27 C39 101.42(15) C12 C27 C39 113.22(16) C19 C29 C24 120.4(2) F7 C30 C6 120.6(2) F7 C30 C38 116.8(2) C38 C30 C6 122.6(2) F10 C33 C11 119.7(2) F10 C33 C50 120.3(2) C50 C33 C11 120.0(2) F21 C38 C30 119.7(3) F21 C38 C50 119.9(2) C50 C38 C30 120.3(2) C13 C39 C27 101.85(16) C55 C43 C15 119.8(2) C59 C49 C12 121.0(2) F22 C50 C33 120.4(3) F22 C50 C38 120.5(2) C33 C50 C38 119.1(2) C59 C55 C43 119.8(2) C55 C59 C49 120.4(3) C16 N14 N23 109.37(19) N14 C16 C20 120.8(2) N14 C16 C53 113.3(2) C20 C16 C53 125.8(2) C46 C18 C28 121.1(2) C31 C20 C16 122.7(2) C31 C20 C34 114.3(2) C34 C20 C16 123.0(2) N14 N23 C28 119.24(18) N14 N23 C37 113.11(19) C28 N23 C37 124.8(2) C54 C25 C37 123.0(2) C54 C25 C56 118.5(2) C56 C25 C37 118.3(2) C18 C28 N23 120.9(2) C18 C28 C42 118.5(2) C42 C28 N23 120.6(2) F26 C31 C20 119.5(2) F26 C31 C45 116.8(3) C45 C31 C20 123.7(3) C36 O32 C58 118.2(2) F4 C34 C20 120.9(2) F4 C34 C40 116.3(2) C40 C34 C20 122.8(3) O32 C36 C41 116.5(2) O32 C36 C46 124.5(2) C46 C36 C41 119.0(2) N23 C37 C25 113.08(19) N23 C37 C53 101.76(19) C25 C37 C53 111.7(2) F35 C40 C34 119.7(3) F35 C40 C47 119.9(3) C47 C40 C34 120.3(3) C42 C41 C36 121.0(2) C41 C42 C28 120.4(2) C47 C45 C31 119.3(3) F48 C45 C31 119.4(3) F48 C45 C47 121.3(3) C18 C46 C36 120.0(2) F44 C47 C40 120.8(3) F44 C47 C45 119.7(3) C45 C47 C40 119.4(3) C57 C52 C60 120.2(3) C16 C53 C37 102.4(2) C25 C54 C60 119.9(2) C57 C56 C25 121.0(3) C52 C57 C56 120.6(3) C52 C60 C54 119.7(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C11 1.338(2) N2 C5 1.401(2) N2 N8 1.372(2) N2 C27 1.472(2) C3 C5 1.387(3) C3 C17 1.382(3) C5 C24 1.394(3) C6 C11 1.392(3) C6 C13 1.463(3) C6 C30 1.392(3) F7 C30 1.334(3) N8 C13 1.285(3) O9 C19 1.376(3) O9 C51 1.408(3) F10 C33 1.340(3) C11 C33 1.372(3) C12 C15 1.371(3) C12 C27 1.511(3) C12 C49 1.372(3) C13 C39 1.503(3) C15 C43 1.387(3) C17 C19 1.381(3) C19 C29 1.378(3) F21 C38 1.333(3) F22 C50 1.332(3) C24 C29 1.380(3) C27 C39 1.535(3) C30 C38 1.374(3) C33 C50 1.366(4) C38 C50 1.372(4) C43 C55 1.370(4) C49 C59 1.372(3) C55 C59 1.353(4) F4 C34 1.338(3) N14 C16 1.288(3) N14 N23 1.361(3) C16 C20 1.462(3) C16 C53 1.497(3) C18 C28 1.386(3) C18 C46 1.379(3) C20 C31 1.391(3) C20 C34 1.396(3) N23 C28 1.399(3) N23 C37 1.467(3) C25 C37 1.513(3) C25 C54 1.371(3) C25 C56 1.377(3) F26 C31 1.348(3) C28 C42 1.388(3) C31 C45 1.377(4) O32 C36 1.367(3) O32 C58 1.412(4) C34 C40 1.372(4) F35 C40 1.337(3) C36 C41 1.383(4) C36 C46 1.382(3) C37 C53 1.542(4) C40 C47 1.369(4) C41 C42 1.370(4) F44 C47 1.335(3) C45 C47 1.367(4) C45 F48 1.332(3) C52 C57 1.344(4) C52 C60 1.364(4) C54 C60 1.405(4) C56 C57 1.369(4)