#------------------------------------------------------------------------------ #$Date: 2018-01-16 03:49:28 +0200 (Tue, 16 Jan 2018) $ #$Revision: 205235 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/11/7121145.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_7121145 loop_ _publ_author_name 'Yu, Ling' 'Wu, Zhongbin' 'Xie, Guohua' 'Zhong, Cheng' 'Zhu, Zece' 'Ma, Dongge' 'Yang, Chuluo' _publ_section_title ; Efficient Excitons Harvest Route for High-Performance OLEDs Based on Aggregation-Induced Delayed Fluorescence ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C7CC09925H _journal_year 2018 _chemical_formula_sum 'C44 H26 F2 N4 O2' _chemical_formula_weight 680.69 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2017-06-10 deposited with the CCDC. 2018-01-15 downloaded from the CCDC. ; _cell_angle_alpha 91.7970(10) _cell_angle_beta 102.7450(10) _cell_angle_gamma 101.0400(10) _cell_formula_units_Z 2 _cell_length_a 11.2482(6) _cell_length_b 11.3076(6) _cell_length_c 13.5181(7) _cell_measurement_reflns_used 9946 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 28.30 _cell_measurement_theta_min 2.36 _cell_volume 1641.10(15) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_unetI/netI 0.0234 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 32873 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.409 _diffrn_reflns_theta_min 1.549 _exptl_absorpt_coefficient_mu 0.094 _exptl_crystal_density_diffrn 1.378 _exptl_crystal_description block _exptl_crystal_F_000 704 _refine_diff_density_max 0.277 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.039 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 469 _refine_ls_number_reflns 8163 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.021 _refine_ls_R_factor_all 0.0776 _refine_ls_R_factor_gt 0.0481 _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^)+(0.0596P)^2^+0.5354P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1207 _refine_ls_wR_factor_ref 0.1423 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5537 _reflns_number_total 8163 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7cc09925h2.cif _cod_data_source_block YL16092A _cod_database_code 7121145 _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_res_file ; YL16092A.res created by SHELXL-2014/7 TITL YL16092A in P-1 CELL 0.71073 11.2482 11.3076 13.5181 91.797 102.745 101.040 ZERR 2.00 0.0006 0.0006 0.0007 0.001 0.001 0.001 LATT 1 SFAC C H N O F UNIT 88 52 8 4 4 L.S. 20 ACTA BOND FMAP 2 PLAN 9 TEMP 23.000 WGHT 0.059600 0.535400 FVAR 0.16692 MOLE 1 N1 3 0.214030 -0.059814 0.222176 11.00000 0.03820 0.03016 = 0.04094 0.00449 0.01723 0.00411 N2 3 0.108092 0.045231 0.364057 11.00000 0.04083 0.03194 = 0.04744 0.00475 0.02255 0.00563 C1 1 0.251263 0.055645 0.254309 11.00000 0.03171 0.03036 = 0.03662 0.00610 0.01388 0.00470 F2 5 -0.150161 -0.336681 0.371437 11.00000 0.06634 0.05532 = 0.09731 0.01837 0.04174 -0.01293 C3 1 0.070554 -0.074488 0.332417 11.00000 0.03515 0.03275 = 0.04207 0.00813 0.01552 0.00435 C9 1 0.355863 0.122758 0.214086 11.00000 0.03283 0.02999 = 0.04073 0.00673 0.01752 0.00517 C44 1 0.244329 0.673003 0.484202 11.00000 0.04470 0.03322 = 0.04266 -0.00249 0.01357 0.00476 C2 1 0.194174 0.109402 0.324429 11.00000 0.03561 0.02922 = 0.04118 0.00387 0.01636 0.00488 C4 1 0.122453 -0.126322 0.260023 11.00000 0.03663 0.02975 = 0.03942 0.00683 0.01377 0.00320 N4 3 0.303092 0.618664 0.418790 11.00000 0.06938 0.02644 = 0.06789 -0.00386 0.04134 -0.00136 C5 1 0.081342 -0.250131 0.227309 11.00000 0.05197 0.03236 = 0.04453 0.00285 0.01593 0.00258 AFIX 43 H5 2 0.114960 -0.285535 0.179791 11.00000 -1.20000 AFIX 0 C15 1 0.223612 0.242455 0.351265 11.00000 0.03754 0.02900 = 0.04732 0.00154 0.02205 0.00362 F1 5 -0.048875 -0.435052 0.239829 11.00000 0.08505 0.03336 = 0.08283 0.00282 0.02344 -0.01269 C8 1 -0.023601 -0.146430 0.371109 11.00000 0.04171 0.04390 = 0.05578 0.01086 0.02532 0.00406 AFIX 43 H8 2 -0.058999 -0.113439 0.418621 11.00000 -1.20000 AFIX 0 C6 1 -0.008160 -0.315926 0.266827 11.00000 0.05273 0.02873 = 0.05242 0.00676 0.00835 -0.00481 C21 1 0.752131 0.193110 0.097949 11.00000 0.03853 0.04603 = 0.04280 -0.00033 0.01893 0.00531 C39 1 0.272717 0.798296 0.503060 11.00000 0.04173 0.03468 = 0.05036 -0.00306 0.00950 0.00459 N3 3 0.667443 0.269021 0.099158 11.00000 0.04714 0.04225 = 0.07799 0.01363 0.04174 0.00751 O2 4 0.356291 0.870916 0.458004 11.00000 0.07017 0.02984 = 0.09405 -0.00492 0.03938 -0.00013 O1 4 0.862761 0.334670 0.002456 11.00000 0.07416 0.05521 = 0.09778 0.01330 0.06466 0.00962 C33 1 0.391317 0.691396 0.376215 11.00000 0.04936 0.03357 = 0.04583 0.00365 0.01727 0.00289 C10 1 0.359591 0.094221 0.114039 11.00000 0.04263 0.04138 = 0.04145 0.00050 0.01651 -0.00094 AFIX 43 H10 2 0.293917 0.039502 0.072410 11.00000 -1.20000 AFIX 0 C38 1 0.417077 0.816053 0.397779 11.00000 0.04722 0.03481 = 0.05014 0.00550 0.01242 0.00519 C12 1 0.559193 0.225889 0.137883 11.00000 0.03913 0.03749 = 0.05608 0.00983 0.02766 0.00646 C7 1 -0.060879 -0.264406 0.337290 11.00000 0.04195 0.04185 = 0.05977 0.01761 0.01947 -0.00385 C14 1 0.454936 0.204729 0.274653 11.00000 0.03950 0.04445 = 0.04224 -0.00060 0.01900 0.00145 AFIX 43 H14 2 0.452936 0.225973 0.341199 11.00000 -1.20000 AFIX 0 C32 1 0.696853 0.387572 0.071249 11.00000 0.03931 0.04384 = 0.04894 0.00800 0.02091 0.00142 C13 1 0.556881 0.255347 0.237160 11.00000 0.03554 0.04504 = 0.05303 -0.00095 0.01700 -0.00046 AFIX 43 H13 2 0.623502 0.308997 0.278812 11.00000 -1.20000 AFIX 0 C43 1 0.156799 0.607686 0.530213 11.00000 0.05421 0.03987 = 0.05656 -0.00035 0.02266 0.00420 AFIX 43 H43 2 0.136104 0.523947 0.518938 11.00000 -1.20000 AFIX 0 C18 1 0.274356 0.490539 0.396218 11.00000 0.05259 0.02750 = 0.05496 -0.00019 0.02777 0.00243 C11 1 0.460258 0.146623 0.075992 11.00000 0.05207 0.04839 = 0.04275 0.00459 0.02592 0.00384 AFIX 43 H11 2 0.461162 0.128351 0.008637 11.00000 -1.20000 AFIX 0 C27 1 0.794757 0.418389 0.022804 11.00000 0.04311 0.04859 = 0.05328 0.00446 0.02339 0.00090 C41 1 0.128813 0.789115 0.610097 11.00000 0.05391 0.06614 = 0.05604 -0.01337 0.01545 0.01910 AFIX 43 H41 2 0.090161 0.827782 0.651880 11.00000 -1.20000 AFIX 0 C22 1 0.743175 0.083963 0.141922 11.00000 0.05238 0.05604 = 0.04631 0.00835 0.02218 0.01463 AFIX 43 H22 2 0.677722 0.057750 0.172863 11.00000 -1.20000 AFIX 0 C26 1 0.850771 0.229154 0.051584 11.00000 0.04191 0.05046 = 0.05134 -0.00374 0.02198 0.00264 C40 1 0.215930 0.855404 0.564913 11.00000 0.05121 0.04155 = 0.06288 -0.01315 0.00853 0.01125 AFIX 43 H40 2 0.236220 0.939126 0.576444 11.00000 -1.20000 AFIX 0 C25 1 0.937364 0.159202 0.050011 11.00000 0.04020 0.06920 = 0.06067 -0.00815 0.02142 0.00749 AFIX 43 H25 2 1.002331 0.184557 0.018347 11.00000 -1.20000 AFIX 0 C23 1 0.830830 0.013168 0.140353 11.00000 0.06371 0.06292 = 0.04843 0.00664 0.01459 0.02455 AFIX 43 H23 2 0.823586 -0.060284 0.169870 11.00000 -1.20000 AFIX 0 C16 1 0.187235 0.318633 0.277131 11.00000 0.05987 0.03529 = 0.04676 -0.00047 0.00882 0.00830 AFIX 43 H16 2 0.146343 0.286472 0.211581 11.00000 -1.20000 AFIX 0 C19 1 0.311289 0.415426 0.469998 11.00000 0.06428 0.03919 = 0.04457 -0.00437 0.01845 0.00284 AFIX 43 H19 2 0.354763 0.448034 0.534837 11.00000 -1.20000 AFIX 0 C37 1 0.503976 0.890507 0.359055 11.00000 0.06526 0.03809 = 0.07775 0.01354 0.02254 -0.00045 AFIX 43 H37 2 0.518191 0.973754 0.372940 11.00000 -1.20000 AFIX 0 C17 1 0.211466 0.442383 0.300163 11.00000 0.06752 0.03390 = 0.05438 0.00612 0.01409 0.01261 AFIX 43 H17 2 0.185129 0.492889 0.250549 11.00000 -1.20000 AFIX 0 C20 1 0.283821 0.291108 0.447890 11.00000 0.06369 0.03643 = 0.04353 0.00505 0.01991 0.00934 AFIX 43 H20 2 0.306246 0.240549 0.498657 11.00000 -1.20000 AFIX 0 C31 1 0.632918 0.476280 0.087826 11.00000 0.05472 0.05418 = 0.07113 0.01931 0.03399 0.01379 AFIX 43 H31 2 0.568480 0.459025 0.121338 11.00000 -1.20000 AFIX 0 C28 1 0.825608 0.531547 -0.009075 11.00000 0.05535 0.05788 = 0.06803 0.01641 0.03201 -0.00185 AFIX 43 H28 2 0.891003 0.549717 -0.041467 11.00000 -1.20000 AFIX 0 C24 1 0.928301 0.051163 0.095354 11.00000 0.04958 0.07593 = 0.05642 -0.00396 0.01166 0.02566 AFIX 43 H24 2 0.987874 0.004342 0.095438 11.00000 -1.20000 AFIX 0 C42 1 0.099802 0.665438 0.592705 11.00000 0.05532 0.06178 = 0.05737 -0.00052 0.02521 0.00949 AFIX 43 H42 2 0.041468 0.620226 0.623133 11.00000 -1.20000 AFIX 0 C34 1 0.458625 0.644031 0.315794 11.00000 0.07491 0.04511 = 0.06814 -0.00147 0.03823 0.00199 AFIX 43 H34 2 0.443509 0.560982 0.300448 11.00000 -1.20000 AFIX 0 C30 1 0.663545 0.590509 0.055193 11.00000 0.07234 0.05639 = 0.09142 0.02635 0.03803 0.02202 AFIX 43 H30 2 0.618684 0.648815 0.066057 11.00000 -1.20000 AFIX 0 C29 1 0.759640 0.618645 0.006870 11.00000 0.06929 0.05465 = 0.08849 0.02852 0.03404 0.00719 AFIX 43 H29 2 0.779990 0.695582 -0.014855 11.00000 -1.20000 AFIX 0 C35 1 0.547936 0.719080 0.278182 11.00000 0.09248 0.06943 = 0.08770 -0.00034 0.05826 -0.00119 AFIX 43 H35 2 0.593017 0.686303 0.238319 11.00000 -1.20000 AFIX 0 C36 1 0.570150 0.842172 0.299683 11.00000 0.09208 0.06344 = 0.09201 0.01600 0.05398 -0.00629 AFIX 43 H36 2 0.629884 0.892604 0.274063 11.00000 -1.20000 AFIX 0 HKLF 4 REM YL16092A in P-1 REM R1 = 0.0481 for 5537 Fo > 4sig(Fo) and 0.0776 for all 8163 data REM 469 parameters refined using 0 restraints END WGHT 0.0595 0.5348 REM Highest difference peak 0.277, deepest hole -0.232, 1-sigma level 0.039 Q1 1 0.4683 0.7247 0.2181 11.00000 0.05 0.28 Q2 1 0.4958 0.8398 0.2343 11.00000 0.05 0.24 Q3 1 0.2136 0.1810 0.3404 11.00000 0.05 0.23 Q4 1 0.3851 0.6265 0.2608 11.00000 0.05 0.22 Q5 1 0.3165 0.0884 0.2426 11.00000 0.05 0.20 Q6 1 0.1207 -0.1050 0.3202 11.00000 0.05 0.19 Q7 1 0.0683 -0.0982 0.2720 11.00000 0.05 0.19 Q8 1 0.2120 0.0935 0.2811 11.00000 0.05 0.19 Q9 1 0.9002 0.0856 0.0393 11.00000 0.05 0.18 ; _shelx_res_checksum 28550 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 N1 N 0.21403(11) -0.05981(11) 0.22218(10) 0.0355(3) Uani 1 1 d . . N2 N 0.10809(12) 0.04523(11) 0.36406(10) 0.0383(3) Uani 1 1 d . . C1 C 0.25126(13) 0.05565(12) 0.25431(11) 0.0321(3) Uani 1 1 d . . F2 F -0.15016(11) -0.33668(10) 0.37144(10) 0.0726(4) Uani 1 1 d . . C3 C 0.07055(14) -0.07449(13) 0.33242(12) 0.0358(3) Uani 1 1 d . . C9 C 0.35586(13) 0.12276(12) 0.21409(11) 0.0332(3) Uani 1 1 d . . C44 C 0.24433(15) 0.67300(13) 0.48420(12) 0.0402(3) Uani 1 1 d . . C2 C 0.19417(13) 0.10940(12) 0.32443(11) 0.0344(3) Uani 1 1 d . . C4 C 0.12245(14) -0.12632(13) 0.26002(11) 0.0349(3) Uani 1 1 d . . N4 N 0.30309(15) 0.61866(12) 0.41879(12) 0.0522(4) Uani 1 1 d . . C5 C 0.08134(16) -0.25013(14) 0.22731(13) 0.0430(4) Uani 1 1 d . . H5 H 0.1150 -0.2855 0.1798 0.052 Uiso 1 1 calc R U C15 C 0.22361(14) 0.24246(13) 0.35127(12) 0.0365(3) Uani 1 1 d . . F1 F -0.04887(12) -0.43505(9) 0.23983(10) 0.0699(3) Uani 1 1 d . . C8 C -0.02360(15) -0.14643(15) 0.37111(14) 0.0454(4) Uani 1 1 d . . H8 H -0.0590 -0.1134 0.4186 0.054 Uiso 1 1 calc R U C6 C -0.00816(17) -0.31593(14) 0.26683(14) 0.0469(4) Uani 1 1 d . . C21 C 0.75213(15) 0.19311(15) 0.09795(12) 0.0415(4) Uani 1 1 d . . C39 C 0.27272(15) 0.79830(14) 0.50306(13) 0.0430(4) Uani 1 1 d . . N3 N 0.66744(13) 0.26902(13) 0.09916(13) 0.0515(4) Uani 1 1 d . . O2 O 0.35629(13) 0.87092(10) 0.45800(12) 0.0631(4) Uani 1 1 d . . O1 O 0.86276(14) 0.33467(12) 0.00246(12) 0.0689(4) Uani 1 1 d . . C33 C 0.39132(16) 0.69140(14) 0.37621(13) 0.0427(4) Uani 1 1 d . . C10 C 0.35959(15) 0.09422(14) 0.11404(12) 0.0421(4) Uani 1 1 d . . H10 H 0.2939 0.0395 0.0724 0.051 Uiso 1 1 calc R U C38 C 0.41708(16) 0.81605(14) 0.39778(13) 0.0443(4) Uani 1 1 d . . C12 C 0.55919(15) 0.22589(14) 0.13788(13) 0.0416(4) Uani 1 1 d . . C7 C -0.06088(16) -0.26441(15) 0.33729(14) 0.0480(4) Uani 1 1 d . . C14 C 0.45494(14) 0.20473(14) 0.27465(13) 0.0416(4) Uani 1 1 d . . H14 H 0.4529 0.2260 0.3412 0.050 Uiso 1 1 calc R U C32 C 0.69685(15) 0.38757(15) 0.07125(13) 0.0432(4) Uani 1 1 d . . C13 C 0.55688(15) 0.25535(15) 0.23716(13) 0.0447(4) Uani 1 1 d . . H13 H 0.6235 0.3090 0.2788 0.054 Uiso 1 1 calc R U C43 C 0.15680(17) 0.60769(16) 0.53021(14) 0.0495(4) Uani 1 1 d . . H43 H 0.1361 0.5239 0.5189 0.059 Uiso 1 1 calc R U C18 C 0.27436(16) 0.49054(13) 0.39622(13) 0.0434(4) Uani 1 1 d . . C11 C 0.46026(16) 0.14662(15) 0.07599(13) 0.0462(4) Uani 1 1 d . . H11 H 0.4612 0.1284 0.0086 0.055 Uiso 1 1 calc R U C27 C 0.79476(16) 0.41839(16) 0.02280(14) 0.0475(4) Uani 1 1 d . . C41 C 0.12881(18) 0.78911(18) 0.61010(15) 0.0577(5) Uani 1 1 d . . H41 H 0.0902 0.8278 0.6519 0.069 Uiso 1 1 calc R U C22 C 0.74317(17) 0.08396(16) 0.14192(13) 0.0493(4) Uani 1 1 d . . H22 H 0.6777 0.0577 0.1729 0.059 Uiso 1 1 calc R U C26 C 0.85077(16) 0.22915(16) 0.05158(14) 0.0472(4) Uani 1 1 d . . C40 C 0.21593(17) 0.85540(16) 0.56491(15) 0.0527(4) Uani 1 1 d . . H40 H 0.2362 0.9391 0.5764 0.063 Uiso 1 1 calc R U C25 C 0.93736(16) 0.15920(18) 0.05001(15) 0.0559(5) Uani 1 1 d . . H25 H 1.0023 0.1846 0.0183 0.067 Uiso 1 1 calc R U C23 C 0.83083(19) 0.01317(19) 0.14035(14) 0.0564(5) Uani 1 1 d . . H23 H 0.8236 -0.0603 0.1699 0.068 Uiso 1 1 calc R U C16 C 0.18724(17) 0.31863(15) 0.27713(14) 0.0481(4) Uani 1 1 d . . H16 H 0.1463 0.2865 0.2116 0.058 Uiso 1 1 calc R U C19 C 0.31129(18) 0.41543(15) 0.47000(14) 0.0496(4) Uani 1 1 d . . H19 H 0.3548 0.4480 0.5348 0.060 Uiso 1 1 calc R U C37 C 0.50398(19) 0.89051(17) 0.35906(17) 0.0607(5) Uani 1 1 d . . H37 H 0.5182 0.9738 0.3729 0.073 Uiso 1 1 calc R U C17 C 0.21147(18) 0.44238(15) 0.30016(14) 0.0516(4) Uani 1 1 d . . H17 H 0.1851 0.4929 0.2505 0.062 Uiso 1 1 calc R U C20 C 0.28382(17) 0.29111(14) 0.44789(13) 0.0468(4) Uani 1 1 d . . H20 H 0.3062 0.2405 0.4987 0.056 Uiso 1 1 calc R U C31 C 0.63292(18) 0.47628(17) 0.08783(16) 0.0562(5) Uani 1 1 d . . H31 H 0.5685 0.4590 0.1213 0.067 Uiso 1 1 calc R U C28 C 0.82561(18) 0.53155(18) -0.00907(16) 0.0592(5) Uani 1 1 d . . H28 H 0.8910 0.5497 -0.0415 0.071 Uiso 1 1 calc R U C24 C 0.92830(18) 0.0512(2) 0.09535(15) 0.0592(5) Uani 1 1 d . . H24 H 0.9879 0.0043 0.0954 0.071 Uiso 1 1 calc R U C42 C 0.09980(18) 0.66544(18) 0.59270(15) 0.0567(5) Uani 1 1 d . . H42 H 0.0415 0.6202 0.6231 0.068 Uiso 1 1 calc R U C34 C 0.4586(2) 0.64403(17) 0.31579(16) 0.0608(5) Uani 1 1 d . . H34 H 0.4435 0.5610 0.3004 0.073 Uiso 1 1 calc R U C30 C 0.6635(2) 0.59051(19) 0.05519(18) 0.0687(6) Uani 1 1 d . . H30 H 0.6187 0.6488 0.0661 0.082 Uiso 1 1 calc R U C29 C 0.7596(2) 0.61865(19) 0.00687(18) 0.0685(6) Uani 1 1 d . . H29 H 0.7800 0.6956 -0.0149 0.082 Uiso 1 1 calc R U C35 C 0.5479(2) 0.7191(2) 0.2782(2) 0.0798(7) Uani 1 1 d . . H35 H 0.5930 0.6863 0.2383 0.096 Uiso 1 1 calc R U C36 C 0.5702(2) 0.8422(2) 0.2997(2) 0.0801(7) Uani 1 1 d . . H36 H 0.6299 0.8926 0.2741 0.096 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 N1 0.0382(6) 0.0302(6) 0.0409(7) 0.0045(5) 0.0172(6) 0.0041(5) N2 0.0408(7) 0.0319(6) 0.0474(8) 0.0047(5) 0.0226(6) 0.0056(5) C1 0.0317(7) 0.0304(7) 0.0366(8) 0.0061(6) 0.0139(6) 0.0047(6) F2 0.0663(7) 0.0553(7) 0.0973(9) 0.0184(6) 0.0417(7) -0.0129(5) C3 0.0351(7) 0.0328(7) 0.0421(8) 0.0081(6) 0.0155(6) 0.0044(6) C9 0.0328(7) 0.0300(7) 0.0407(8) 0.0067(6) 0.0175(6) 0.0052(6) C44 0.0447(8) 0.0332(7) 0.0427(9) -0.0025(6) 0.0136(7) 0.0048(6) C2 0.0356(7) 0.0292(7) 0.0412(8) 0.0039(6) 0.0164(6) 0.0049(6) C4 0.0366(7) 0.0298(7) 0.0394(8) 0.0068(6) 0.0138(6) 0.0032(6) N4 0.0694(10) 0.0264(6) 0.0679(10) -0.0039(6) 0.0413(8) -0.0014(6) C5 0.0520(9) 0.0324(8) 0.0445(9) 0.0029(6) 0.0159(8) 0.0026(7) C15 0.0375(8) 0.0290(7) 0.0473(9) 0.0015(6) 0.0221(7) 0.0036(6) F1 0.0851(8) 0.0334(5) 0.0828(8) 0.0028(5) 0.0234(7) -0.0127(5) C8 0.0417(9) 0.0439(9) 0.0558(10) 0.0109(7) 0.0253(8) 0.0041(7) C6 0.0527(10) 0.0287(8) 0.0524(10) 0.0068(7) 0.0084(8) -0.0048(7) C21 0.0385(8) 0.0460(9) 0.0428(9) -0.0003(7) 0.0189(7) 0.0053(7) C39 0.0417(8) 0.0347(8) 0.0504(10) -0.0031(7) 0.0095(7) 0.0046(7) N3 0.0471(8) 0.0423(8) 0.0780(11) 0.0136(7) 0.0417(8) 0.0075(6) O2 0.0702(9) 0.0298(6) 0.0940(11) -0.0049(6) 0.0394(8) -0.0001(6) O1 0.0742(9) 0.0552(8) 0.0978(11) 0.0133(7) 0.0647(9) 0.0096(7) C33 0.0494(9) 0.0336(8) 0.0458(9) 0.0036(7) 0.0173(8) 0.0029(7) C10 0.0426(8) 0.0414(8) 0.0414(9) 0.0005(7) 0.0165(7) -0.0009(7) C38 0.0472(9) 0.0348(8) 0.0501(10) 0.0055(7) 0.0124(8) 0.0052(7) C12 0.0391(8) 0.0375(8) 0.0561(10) 0.0098(7) 0.0277(8) 0.0065(6) C7 0.0419(9) 0.0419(9) 0.0598(11) 0.0176(8) 0.0195(8) -0.0038(7) C14 0.0395(8) 0.0444(9) 0.0422(9) -0.0006(7) 0.0190(7) 0.0014(7) C32 0.0393(8) 0.0438(9) 0.0489(10) 0.0080(7) 0.0209(7) 0.0014(7) C13 0.0355(8) 0.0450(9) 0.0530(10) -0.0010(7) 0.0170(7) -0.0005(7) C43 0.0542(10) 0.0399(9) 0.0566(11) -0.0004(8) 0.0227(9) 0.0042(8) C18 0.0526(9) 0.0275(7) 0.0550(10) -0.0002(7) 0.0278(8) 0.0024(7) C11 0.0521(10) 0.0484(9) 0.0427(9) 0.0046(7) 0.0259(8) 0.0038(8) C27 0.0431(9) 0.0486(9) 0.0533(10) 0.0045(8) 0.0234(8) 0.0009(7) C41 0.0539(11) 0.0661(12) 0.0560(11) -0.0134(9) 0.0155(9) 0.0191(9) C22 0.0524(10) 0.0560(10) 0.0463(10) 0.0084(8) 0.0222(8) 0.0146(8) C26 0.0419(9) 0.0505(10) 0.0513(10) -0.0037(8) 0.0220(8) 0.0026(7) C40 0.0512(10) 0.0416(9) 0.0629(12) -0.0132(8) 0.0085(9) 0.0112(8) C25 0.0402(9) 0.0692(12) 0.0607(12) -0.0082(9) 0.0214(9) 0.0075(8) C23 0.0637(12) 0.0629(11) 0.0484(11) 0.0066(9) 0.0146(9) 0.0246(10) C16 0.0599(10) 0.0353(8) 0.0468(10) -0.0005(7) 0.0088(8) 0.0083(7) C19 0.0643(11) 0.0392(9) 0.0446(10) -0.0044(7) 0.0185(8) 0.0028(8) C37 0.0653(12) 0.0381(9) 0.0777(14) 0.0135(9) 0.0225(11) -0.0005(8) C17 0.0675(11) 0.0339(8) 0.0544(11) 0.0061(7) 0.0141(9) 0.0126(8) C20 0.0637(11) 0.0364(8) 0.0435(9) 0.0051(7) 0.0199(8) 0.0093(8) C31 0.0547(10) 0.0542(11) 0.0711(13) 0.0193(9) 0.0340(10) 0.0138(9) C28 0.0553(11) 0.0579(11) 0.0680(13) 0.0164(9) 0.0320(10) -0.0018(9) C24 0.0496(10) 0.0759(13) 0.0564(12) -0.0040(10) 0.0117(9) 0.0257(10) C42 0.0553(11) 0.0618(12) 0.0574(12) -0.0005(9) 0.0252(9) 0.0095(9) C34 0.0749(13) 0.0451(10) 0.0681(13) -0.0015(9) 0.0382(11) 0.0020(9) C30 0.0723(13) 0.0564(12) 0.0914(16) 0.0264(11) 0.0380(12) 0.0220(10) C29 0.0693(13) 0.0547(11) 0.0885(16) 0.0285(11) 0.0340(12) 0.0072(10) C35 0.0925(17) 0.0694(14) 0.0877(17) -0.0003(12) 0.0583(15) -0.0012(12) C36 0.0921(17) 0.0634(14) 0.0920(18) 0.0160(12) 0.0540(15) -0.0063(12) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C4 117.63(12) C2 N2 C3 117.31(12) N1 C1 C2 120.95(12) N1 C1 C9 115.32(12) C2 C1 C9 123.73(12) N2 C3 C4 120.78(13) N2 C3 C8 119.34(13) C4 C3 C8 119.86(14) C14 C9 C10 118.64(13) C14 C9 C1 122.65(13) C10 C9 C1 118.47(13) C43 C44 C39 117.76(14) C43 C44 N4 122.97(14) C39 C44 N4 119.25(14) N2 C2 C1 121.97(13) N2 C2 C15 116.32(12) C1 C2 C15 121.60(12) N1 C4 C3 121.25(13) N1 C4 C5 118.78(13) C3 C4 C5 119.95(13) C33 N4 C44 119.23(13) C33 N4 C18 120.04(12) C44 N4 C18 120.72(13) C6 C5 C4 118.29(15) C20 C15 C16 119.25(14) C20 C15 C2 121.72(14) C16 C15 C2 119.02(14) C7 C8 C3 118.31(15) F1 C6 C5 120.70(16) F1 C6 C7 117.48(14) C5 C6 C7 121.82(15) C22 C21 C26 118.15(15) C22 C21 N3 122.90(14) C26 C21 N3 118.94(15) C40 C39 O2 117.03(14) C40 C39 C44 121.26(16) O2 C39 C44 121.68(14) C21 N3 C32 118.87(13) C21 N3 C12 118.53(13) C32 N3 C12 122.35(13) C38 O2 C39 118.31(12) C26 O1 C27 117.53(12) C34 C33 C38 117.89(15) C34 C33 N4 122.67(15) C38 C33 N4 119.39(14) C11 C10 C9 120.55(15) C37 C38 O2 116.61(15) C37 C38 C33 121.39(16) O2 C38 C33 122.00(15) C11 C12 C13 120.12(14) C11 C12 N3 118.55(15) C13 C12 N3 121.16(15) F2 C7 C8 120.71(16) F2 C7 C6 117.53(15) C8 C7 C6 121.75(14) C13 C14 C9 120.80(15) C31 C32 C27 117.60(15) C31 C32 N3 123.53(14) C27 C32 N3 118.87(15) C12 C13 C14 119.81(15) C42 C43 C44 120.88(16) C17 C18 C19 119.86(15) C17 C18 N4 119.91(16) C19 C18 N4 120.22(16) C12 C11 C10 120.06(15) C28 C27 O1 117.03(15) C28 C27 C32 121.66(17) O1 C27 C32 121.29(15) C42 C41 C40 119.33(16) C21 C22 C23 120.66(16) C25 C26 O1 117.44(15) C25 C26 C21 121.19(17) O1 C26 C21 121.34(15) C39 C40 C41 120.30(16) C26 C25 C24 120.10(17) C24 C23 C22 120.23(19) C17 C16 C15 120.36(17) C18 C19 C20 120.18(17) C38 C37 C36 119.99(18) C18 C17 C16 120.04(16) C15 C20 C19 120.26(16) C32 C31 C30 120.81(17) C27 C28 C29 119.98(17) C23 C24 C25 119.65(17) C41 C42 C43 120.46(18) C35 C34 C33 120.69(18) C29 C30 C31 120.63(19) C30 C29 C28 119.31(18) C36 C35 C34 120.1(2) C37 C36 C35 119.93(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C1 1.3204(18) N1 C4 1.3596(18) N2 C2 1.3173(18) N2 C3 1.3634(19) C1 C2 1.4361(18) C1 C9 1.4906(18) F2 C7 1.3429(18) C3 C4 1.410(2) C3 C8 1.414(2) C9 C14 1.388(2) C9 C10 1.392(2) C44 C43 1.386(2) C44 C39 1.394(2) C44 N4 1.4056(19) C2 C15 1.4922(19) C4 C5 1.412(2) N4 C33 1.401(2) N4 C18 1.4304(19) C5 C6 1.352(2) C15 C20 1.375(2) C15 C16 1.386(2) F1 C6 1.3478(18) C8 C7 1.352(2) C6 C7 1.395(3) C21 C22 1.383(2) C21 C26 1.393(2) C21 N3 1.401(2) C39 C40 1.373(2) C39 O2 1.385(2) N3 C32 1.402(2) N3 C12 1.4368(18) O2 C38 1.375(2) O1 C26 1.382(2) O1 C27 1.382(2) C33 C34 1.388(2) C33 C38 1.392(2) C10 C11 1.385(2) C38 C37 1.370(2) C12 C11 1.379(2) C12 C13 1.380(2) C14 C13 1.387(2) C32 C31 1.381(2) C32 C27 1.396(2) C43 C42 1.384(2) C18 C17 1.373(3) C18 C19 1.376(3) C27 C28 1.369(2) C41 C42 1.374(3) C41 C40 1.381(3) C22 C23 1.387(2) C26 C25 1.370(2) C25 C24 1.380(3) C23 C24 1.374(3) C16 C17 1.385(2) C19 C20 1.388(2) C37 C36 1.374(3) C31 C30 1.383(3) C28 C29 1.380(3) C34 C35 1.383(3) C30 C29 1.374(3) C35 C36 1.376(3)