#------------------------------------------------------------------------------ #$Date: 2026-06-04 10:23:32 +0100 (Thu, 04 Jun 2026) $ #$Revision: 306202 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/73/1577358.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_1577358 loop_ _publ_author_name 'Zhang, Qilong' 'Zhou, Xu' 'Shan, Xiaofeng' 'He, Fa' 'Bao, Yuwei' 'Xu, Hong' 'Zhu, Chun' 'Zhu, Bixue' _publ_section_title ; Switching between photochromism and photoluminescence in Schiff base derivatives by molecular design of end groups. ; _journal_issue 18 _journal_name_full 'Chemical science' _journal_page_first 9193 _journal_page_last 9203 _journal_paper_doi 10.1039/d6sc00735j _journal_volume 17 _journal_year 2026 _chemical_formula_moiety 'C33 H24 F N O' _chemical_formula_sum 'C33 H24 F N O' _chemical_formula_weight 469.53 _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_date 2024-11-03 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2025-09-10 deposited with the CCDC. 2026-03-16 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 93.487(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.757(2) _cell_length_b 13.767(3) _cell_length_c 16.963(3) _cell_measurement_reflns_used 8616 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 28.32 _cell_measurement_theta_min 2.82 _cell_volume 2507.4(8) _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_temperature 273.15 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _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 0.0760 _diffrn_reflns_av_unetI/netI 0.0609 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.990 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 35543 _diffrn_reflns_point_group_measured_fraction_full 0.990 _diffrn_reflns_point_group_measured_fraction_max 0.990 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.328 _diffrn_reflns_theta_min 2.638 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_crystal_colour YELLOW _exptl_crystal_density_diffrn 1.244 _exptl_crystal_description BLOCK _exptl_crystal_F_000 984 _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.726 _refine_diff_density_min -0.491 _refine_diff_density_rms 0.051 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 326 _refine_ls_number_reflns 6192 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.116 _refine_ls_R_factor_all 0.1601 _refine_ls_R_factor_gt 0.0999 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1020P)^2^+1.9779P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2349 _refine_ls_wR_factor_ref 0.2686 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3707 _reflns_number_total 6192 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc00735j2.cif _cod_data_source_block a_CCDC1 _cod_original_cell_volume 2507.7(9) _cod_database_code 1577358 _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_max 0.986 _shelx_estimated_absorpt_t_min 0.984 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C25(H25), C26(H26), C27(H27), C32(H32), C31(H31), C30(H30), C29(H29) 2.b Idealised tetrahedral OH refined as rotating group: O1(H1) ; _shelx_res_file ; a.res created by SHELXL-2014/7 TITL A_a.res in P2(1)/n CELL 0.71073 10.7575 13.7675 16.9633 90 93.487 90 ZERR 4 0.0023 0.003 0.0034 0 0.007 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N O F UNIT 132 96 4 4 4 L.S. 4 PLAN -5 0 0 SIZE 0.21 0.19 0.18 TEMP 0 HTAB O1 N1 CONF fmap 2 acta REM REM REM WGHT 0.102000 1.977900 FVAR 1.29500 F1 5 0.483466 0.284076 0.328469 11.00000 0.11653 0.10901 = 0.15490 0.01395 0.04673 -0.01488 O1 4 0.667035 0.527902 0.443064 11.00000 0.12257 0.07237 = 0.07805 -0.01487 -0.03999 0.05124 AFIX 147 H1 2 0.663613 0.489174 0.406271 11.00000 -1.50000 AFIX 0 N1 3 0.585827 0.457349 0.305121 11.00000 0.06948 0.04497 = 0.06161 -0.00828 -0.00851 0.01687 C1 1 0.399523 0.905682 0.281120 11.00000 0.05428 0.02996 = 0.04473 -0.00954 0.00451 0.00357 C2 1 0.514592 0.922325 0.250809 11.00000 0.06590 0.04531 = 0.06631 -0.01193 0.01480 0.00510 AFIX 43 H2 2 0.587250 0.909530 0.281586 11.00000 -1.20000 AFIX 0 C3 1 0.521507 0.958149 0.174397 11.00000 0.11086 0.04814 = 0.08415 -0.01120 0.05416 -0.00031 AFIX 43 H3 2 0.598692 0.970518 0.154617 11.00000 -1.20000 AFIX 0 C4 1 0.414084 0.975249 0.128150 11.00000 0.15238 0.05404 = 0.04869 -0.00266 0.01866 0.01141 AFIX 43 H4 2 0.418770 0.999197 0.077153 11.00000 -1.20000 AFIX 0 C5 1 0.301843 0.957268 0.156789 11.00000 0.11290 0.06296 = 0.04843 -0.00755 -0.01151 0.01557 AFIX 43 H5 2 0.229742 0.967942 0.124893 11.00000 -1.20000 AFIX 0 C6 1 0.292911 0.923449 0.232364 11.00000 0.06644 0.04720 = 0.04725 -0.01068 -0.00677 0.00399 AFIX 43 H6 2 0.214824 0.912258 0.251263 11.00000 -1.20000 AFIX 0 C7 1 0.390705 0.867241 0.362886 11.00000 0.04272 0.03326 = 0.04504 -0.00775 -0.00257 0.00089 C8 1 0.315884 0.906907 0.415116 11.00000 0.03945 0.03431 = 0.04554 -0.00037 -0.00144 0.00130 C9 1 0.250821 1.001835 0.403228 11.00000 0.04016 0.03573 = 0.03384 -0.00219 -0.00033 0.00255 C10 1 0.308577 1.083715 0.375526 11.00000 0.04118 0.03930 = 0.05083 -0.00633 0.00410 -0.00207 AFIX 43 H10 2 0.390970 1.080106 0.362058 11.00000 -1.20000 AFIX 0 C11 1 0.245024 1.171089 0.367614 11.00000 0.06866 0.03281 = 0.05391 -0.00159 -0.00107 -0.00387 AFIX 43 H11 2 0.284982 1.225243 0.348319 11.00000 -1.20000 AFIX 0 C12 1 0.124579 1.178593 0.387789 11.00000 0.07029 0.04721 = 0.04879 -0.00175 -0.00074 0.02191 AFIX 43 H12 2 0.082932 1.237683 0.382893 11.00000 -1.20000 AFIX 0 C13 1 0.065507 1.098589 0.415270 11.00000 0.04460 0.06855 = 0.05525 0.01252 0.00701 0.02099 AFIX 43 H13 2 -0.016975 1.103200 0.428392 11.00000 -1.20000 AFIX 0 C14 1 0.127313 1.011231 0.423651 11.00000 0.04556 0.04830 = 0.04759 0.01276 0.00595 0.00501 AFIX 43 H14 2 0.086346 0.957695 0.443174 11.00000 -1.20000 AFIX 0 C15 1 0.288184 0.856241 0.490240 11.00000 0.04072 0.04243 = 0.05185 0.00823 0.00376 0.01069 C16 1 0.234000 0.765198 0.488212 11.00000 0.05880 0.05241 = 0.07467 0.01511 0.00522 0.00244 AFIX 43 H16 2 0.218738 0.733912 0.440004 11.00000 -1.20000 AFIX 0 C17 1 0.202260 0.720132 0.556778 11.00000 0.06882 0.06467 = 0.10672 0.03919 0.00821 0.00086 AFIX 43 H17 2 0.165713 0.658905 0.554275 11.00000 -1.20000 AFIX 0 C18 1 0.223557 0.763689 0.627003 11.00000 0.07366 0.09620 = 0.08799 0.05512 0.01423 0.01965 AFIX 43 H18 2 0.201353 0.732832 0.672847 11.00000 -1.20000 AFIX 0 C19 1 0.278290 0.854088 0.631254 11.00000 0.08710 0.09543 = 0.05463 0.02265 0.00229 0.03138 AFIX 43 H19 2 0.294561 0.883853 0.680006 11.00000 -1.20000 AFIX 0 C20 1 0.309216 0.900817 0.562292 11.00000 0.06530 0.05672 = 0.05269 0.01026 0.00159 0.01371 AFIX 43 H20 2 0.344305 0.962552 0.565033 11.00000 -1.20000 AFIX 0 C21 1 0.466770 0.778054 0.382425 11.00000 0.04185 0.03819 = 0.04824 -0.00622 -0.00111 0.00594 C22 1 0.469752 0.701862 0.330340 11.00000 0.04893 0.04033 = 0.04367 -0.00289 -0.00731 0.00734 AFIX 43 H22 2 0.426234 0.707373 0.281471 11.00000 -1.20000 AFIX 0 C23 1 0.535752 0.616283 0.347992 11.00000 0.05364 0.03805 = 0.04841 -0.00498 -0.00471 0.00969 C24 1 0.603629 0.609510 0.421285 11.00000 0.06262 0.05252 = 0.06047 -0.00358 -0.01680 0.02175 C25 1 0.603914 0.686573 0.472872 11.00000 0.07146 0.07344 = 0.05407 -0.01626 -0.02644 0.02821 AFIX 43 H25 2 0.649273 0.682370 0.521201 11.00000 -1.20000 AFIX 0 C26 1 0.538395 0.769237 0.454017 11.00000 0.05703 0.05516 = 0.05295 -0.01995 -0.01226 0.01247 AFIX 43 H26 2 0.541332 0.820854 0.489446 11.00000 -1.20000 AFIX 0 C27 1 0.533038 0.538542 0.291022 11.00000 0.05657 0.04268 = 0.05140 -0.00436 -0.00635 0.00761 AFIX 43 H27 2 0.491052 0.548196 0.242096 11.00000 -1.20000 AFIX 0 C28 1 0.582422 0.385597 0.244885 11.00000 0.05505 0.04094 = 0.06574 -0.00532 -0.00948 0.01378 C32 1 0.521827 0.224356 0.205402 11.00000 0.12375 0.05862 = 0.10101 -0.02213 -0.01352 -0.00716 AFIX 43 H32 2 0.479125 0.167442 0.215646 11.00000 -1.20000 AFIX 0 C31 1 0.578626 0.236236 0.136545 11.00000 0.13420 0.06793 = 0.10021 -0.03680 -0.03166 0.03001 AFIX 43 H31 2 0.578746 0.185594 0.100268 11.00000 -1.20000 AFIX 0 C30 1 0.636578 0.323722 0.120035 11.00000 0.11501 0.10568 = 0.06467 -0.01069 0.00631 0.04453 AFIX 43 H30 2 0.675278 0.331716 0.072911 11.00000 -1.20000 AFIX 0 C29 1 0.636072 0.397183 0.173309 11.00000 0.08900 0.07265 = 0.06719 -0.00291 0.00320 0.01861 AFIX 43 H29 2 0.672373 0.456337 0.161566 11.00000 -1.20000 AFIX 0 C33 1 0.529199 0.297133 0.258110 11.00000 0.06364 0.05973 = 0.08400 -0.00059 0.00565 0.00413 HKLF 4 REM A_a.res in P2(1)/n REM R1 = 0.0999 for 3707 Fo > 4sig(Fo) and 0.1601 for all 6192 data REM 326 parameters refined using 0 restraints END WGHT 0.1020 1.9780 REM Highest difference peak 0.726, deepest hole -0.491, 1-sigma level 0.051 Q1 1 0.6892 0.4770 0.1711 11.00000 0.05 0.73 Q2 1 0.4201 0.8205 0.3756 11.00000 0.05 0.25 Q3 1 0.3927 0.9082 0.4041 11.00000 0.05 0.24 Q4 1 0.3235 0.8623 0.3730 11.00000 0.05 0.24 Q5 1 0.2009 1.0149 0.4337 11.00000 0.05 0.23 ; _shelx_res_checksum 41865 _olex2_submission_special_instructions 'No special instructions were received' 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 F1 F 0.4835(3) 0.2841(3) 0.3285(2) 0.1252(12) Uani 1 1 d . . . . . O1 O 0.6670(3) 0.5279(2) 0.44306(18) 0.0929(11) Uani 1 1 d . . . . . H1 H 0.6636 0.4892 0.4063 0.139 Uiso 1 1 calc GR . . . . N1 N 0.5858(3) 0.4573(2) 0.30512(17) 0.0592(8) Uani 1 1 d . . . . . C1 C 0.3995(3) 0.9057(2) 0.28112(17) 0.0429(7) Uani 1 1 d . . . . . C2 C 0.5146(4) 0.9223(2) 0.2508(2) 0.0587(9) Uani 1 1 d . . . . . H2 H 0.5872 0.9095 0.2816 0.070 Uiso 1 1 calc R . . . . C3 C 0.5215(5) 0.9581(3) 0.1744(3) 0.0791(14) Uani 1 1 d . . . . . H3 H 0.5987 0.9705 0.1546 0.095 Uiso 1 1 calc R . . . . C4 C 0.4141(6) 0.9752(3) 0.1281(2) 0.0845(15) Uani 1 1 d . . . . . H4 H 0.4188 0.9992 0.0772 0.101 Uiso 1 1 calc R . . . . C5 C 0.3018(5) 0.9573(3) 0.1568(2) 0.0754(12) Uani 1 1 d . . . . . H5 H 0.2297 0.9679 0.1249 0.091 Uiso 1 1 calc R . . . . C6 C 0.2929(3) 0.9234(2) 0.23236(19) 0.0540(8) Uani 1 1 d . . . . . H6 H 0.2148 0.9123 0.2513 0.065 Uiso 1 1 calc R . . . . C7 C 0.3907(3) 0.8672(2) 0.36289(17) 0.0406(7) Uani 1 1 d . . . . . C8 C 0.3159(3) 0.9069(2) 0.41512(17) 0.0399(6) Uani 1 1 d . . . . . C9 C 0.2508(3) 1.0018(2) 0.40323(16) 0.0367(6) Uani 1 1 d . . . . . C10 C 0.3086(3) 1.0837(2) 0.37553(18) 0.0437(7) Uani 1 1 d . . . . . H10 H 0.3910 1.0801 0.3621 0.052 Uiso 1 1 calc R . . . . C11 C 0.2450(3) 1.1711(2) 0.3676(2) 0.0520(8) Uani 1 1 d . . . . . H11 H 0.2850 1.2252 0.3483 0.062 Uiso 1 1 calc R . . . . C12 C 0.1246(3) 1.1786(3) 0.38779(19) 0.0556(9) Uani 1 1 d . . . . . H12 H 0.0829 1.2377 0.3829 0.067 Uiso 1 1 calc R . . . . C13 C 0.0655(3) 1.0986(3) 0.4153(2) 0.0560(9) Uani 1 1 d . . . . . H13 H -0.0170 1.1032 0.4284 0.067 Uiso 1 1 calc R . . . . C14 C 0.1273(3) 1.0112(2) 0.42365(18) 0.0470(7) Uani 1 1 d . . . . . H14 H 0.0863 0.9577 0.4432 0.056 Uiso 1 1 calc R . . . . C15 C 0.2882(3) 0.8562(2) 0.49024(18) 0.0450(7) Uani 1 1 d . . . . . C16 C 0.2340(3) 0.7652(3) 0.4882(2) 0.0619(9) Uani 1 1 d . . . . . H16 H 0.2187 0.7339 0.4400 0.074 Uiso 1 1 calc R . . . . C17 C 0.2023(4) 0.7201(3) 0.5568(3) 0.0800(13) Uani 1 1 d . . . . . H17 H 0.1657 0.6589 0.5543 0.096 Uiso 1 1 calc R . . . . C18 C 0.2236(4) 0.7637(4) 0.6270(3) 0.0856(15) Uani 1 1 d . . . . . H18 H 0.2014 0.7328 0.6728 0.103 Uiso 1 1 calc R . . . . C19 C 0.2783(4) 0.8541(4) 0.6313(2) 0.0791(13) Uani 1 1 d . . . . . H19 H 0.2946 0.8839 0.6800 0.095 Uiso 1 1 calc R . . . . C20 C 0.3092(3) 0.9008(3) 0.5623(2) 0.0583(9) Uani 1 1 d . . . . . H20 H 0.3443 0.9626 0.5650 0.070 Uiso 1 1 calc R . . . . C21 C 0.4668(3) 0.7781(2) 0.38242(18) 0.0429(7) Uani 1 1 d . . . . . C22 C 0.4698(3) 0.7019(2) 0.33034(18) 0.0447(7) Uani 1 1 d . . . . . H22 H 0.4262 0.7074 0.2815 0.054 Uiso 1 1 calc R . . . . C23 C 0.5358(3) 0.6163(2) 0.34799(18) 0.0470(7) Uani 1 1 d . . . . . C24 C 0.6036(3) 0.6095(3) 0.4213(2) 0.0594(9) Uani 1 1 d . . . . . C25 C 0.6039(4) 0.6866(3) 0.4729(2) 0.0676(11) Uani 1 1 d . . . . . H25 H 0.6493 0.6824 0.5212 0.081 Uiso 1 1 calc R . . . . C26 C 0.5384(3) 0.7692(3) 0.4540(2) 0.0557(9) Uani 1 1 d . . . . . H26 H 0.5413 0.8209 0.4894 0.067 Uiso 1 1 calc R . . . . C27 C 0.5330(3) 0.5385(2) 0.2910(2) 0.0506(8) Uani 1 1 d . . . . . H27 H 0.4911 0.5482 0.2421 0.061 Uiso 1 1 calc R . . . . C28 C 0.5824(3) 0.3856(2) 0.2449(2) 0.0544(9) Uani 1 1 d . . . . . C32 C 0.5218(6) 0.2244(3) 0.2054(3) 0.0953(15) Uani 1 1 d . . . . . H32 H 0.4791 0.1674 0.2156 0.114 Uiso 1 1 calc R . . . . C31 C 0.5786(6) 0.2362(4) 0.1365(4) 0.1024(19) Uani 1 1 d . . . . . H31 H 0.5787 0.1856 0.1003 0.123 Uiso 1 1 calc R . . . . C30 C 0.6366(5) 0.3237(4) 0.1200(3) 0.0951(16) Uani 1 1 d . . . . . H30 H 0.6753 0.3317 0.0729 0.114 Uiso 1 1 calc R . . . . C29 C 0.6361(4) 0.3972(3) 0.1733(2) 0.0763(12) Uani 1 1 d . . . . . H29 H 0.6724 0.4563 0.1616 0.092 Uiso 1 1 calc R . . . . C33 C 0.5292(4) 0.2971(3) 0.2581(3) 0.0691(10) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.117(2) 0.109(2) 0.155(3) 0.014(2) 0.047(2) -0.0149(19) O1 0.123(3) 0.0724(19) 0.078(2) -0.0149(15) -0.0400(18) 0.0512(18) N1 0.0695(19) 0.0450(16) 0.0616(18) -0.0083(13) -0.0085(14) 0.0169(14) C1 0.0543(18) 0.0300(14) 0.0447(16) -0.0095(12) 0.0045(13) 0.0036(12) C2 0.066(2) 0.0453(18) 0.066(2) -0.0119(16) 0.0148(17) 0.0051(16) C3 0.111(4) 0.048(2) 0.084(3) -0.011(2) 0.054(3) 0.000(2) C4 0.152(5) 0.054(2) 0.049(2) -0.0027(18) 0.019(3) 0.011(3) C5 0.113(4) 0.063(2) 0.048(2) -0.0075(18) -0.012(2) 0.016(2) C6 0.066(2) 0.0472(18) 0.0473(18) -0.0107(15) -0.0068(15) 0.0040(16) C7 0.0427(15) 0.0333(14) 0.0450(16) -0.0077(12) -0.0026(12) 0.0009(12) C8 0.0395(15) 0.0343(14) 0.0455(16) -0.0004(12) -0.0014(12) 0.0013(12) C9 0.0402(15) 0.0357(14) 0.0338(14) -0.0022(11) -0.0003(11) 0.0026(12) C10 0.0412(16) 0.0393(16) 0.0508(17) -0.0063(13) 0.0041(13) -0.0021(13) C11 0.069(2) 0.0328(15) 0.0539(19) -0.0016(14) -0.0011(16) -0.0039(15) C12 0.070(2) 0.0472(19) 0.0488(18) -0.0017(15) -0.0007(16) 0.0219(17) C13 0.0446(17) 0.069(2) 0.0552(19) 0.0125(17) 0.0070(14) 0.0210(16) C14 0.0456(17) 0.0483(17) 0.0476(17) 0.0128(14) 0.0059(13) 0.0050(14) C15 0.0407(16) 0.0424(16) 0.0518(18) 0.0082(14) 0.0038(13) 0.0107(13) C16 0.059(2) 0.052(2) 0.075(2) 0.0151(18) 0.0052(17) 0.0024(17) C17 0.069(3) 0.065(3) 0.107(4) 0.039(3) 0.008(2) 0.001(2) C18 0.074(3) 0.096(4) 0.088(3) 0.055(3) 0.014(2) 0.020(3) C19 0.087(3) 0.095(3) 0.055(2) 0.023(2) 0.002(2) 0.031(3) C20 0.065(2) 0.057(2) 0.053(2) 0.0103(16) 0.0016(16) 0.0137(17) C21 0.0418(16) 0.0382(15) 0.0482(17) -0.0062(13) -0.0011(12) 0.0059(12) C22 0.0489(17) 0.0403(16) 0.0437(16) -0.0029(13) -0.0073(13) 0.0073(13) C23 0.0536(18) 0.0380(16) 0.0484(17) -0.0050(13) -0.0047(13) 0.0097(13) C24 0.063(2) 0.053(2) 0.060(2) -0.0036(16) -0.0168(16) 0.0218(17) C25 0.071(2) 0.073(3) 0.054(2) -0.0163(18) -0.0264(17) 0.028(2) C26 0.057(2) 0.055(2) 0.0530(19) -0.0200(16) -0.0123(15) 0.0125(16) C27 0.0566(19) 0.0427(17) 0.0514(18) -0.0044(14) -0.0064(14) 0.0076(15) C28 0.0550(19) 0.0409(17) 0.066(2) -0.0053(15) -0.0095(16) 0.0138(15) C32 0.124(4) 0.059(3) 0.101(4) -0.022(3) -0.014(3) -0.007(3) C31 0.134(5) 0.068(3) 0.100(4) -0.037(3) -0.032(3) 0.030(3) C30 0.115(4) 0.106(4) 0.065(3) -0.011(3) 0.006(3) 0.045(3) C29 0.089(3) 0.073(3) 0.067(3) -0.003(2) 0.003(2) 0.019(2) C33 0.064(2) 0.060(2) 0.084(3) -0.001(2) 0.006(2) 0.0041(19) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C27 N1 C28 119.0(3) . . ? C2 C1 C6 118.1(3) . . ? C2 C1 C7 120.7(3) . . ? C6 C1 C7 121.1(3) . . ? C1 C2 C3 120.2(4) . . ? C4 C3 C2 120.0(4) . . ? C5 C4 C3 120.1(4) . . ? C4 C5 C6 120.8(4) . . ? C5 C6 C1 120.8(4) . . ? C1 C7 C21 115.5(2) . . ? C8 C7 C1 122.8(3) . . ? C8 C7 C21 121.7(3) . . ? C7 C8 C9 124.1(3) . . ? C7 C8 C15 121.9(3) . . ? C9 C8 C15 114.0(2) . . ? C10 C9 C8 122.9(3) . . ? C10 C9 C14 117.5(3) . . ? C14 C9 C8 119.5(3) . . ? C9 C10 C11 120.7(3) . . ? C12 C11 C10 120.8(3) . . ? C11 C12 C13 119.5(3) . . ? C12 C13 C14 120.5(3) . . ? C13 C14 C9 121.0(3) . . ? C16 C15 C8 120.4(3) . . ? C20 C15 C8 121.2(3) . . ? C20 C15 C16 118.3(3) . . ? C17 C16 C15 120.8(4) . . ? C18 C17 C16 120.7(4) . . ? C17 C18 C19 120.0(4) . . ? C18 C19 C20 119.8(4) . . ? C15 C20 C19 120.4(4) . . ? C22 C21 C7 121.1(3) . . ? C22 C21 C26 117.2(3) . . ? C26 C21 C7 121.7(3) . . ? C21 C22 C23 122.5(3) . . ? C22 C23 C24 118.3(3) . . ? C22 C23 C27 119.5(3) . . ? C24 C23 C27 122.1(3) . . ? O1 C24 C23 121.5(3) . . ? O1 C24 C25 119.0(3) . . ? C25 C24 C23 119.5(3) . . ? C26 C25 C24 120.8(3) . . ? C25 C26 C21 121.5(3) . . ? N1 C27 C23 122.5(3) . . ? C29 C28 N1 123.8(4) . . ? C33 C28 N1 119.6(4) . . ? C33 C28 C29 116.5(4) . . ? C33 C32 C31 118.1(5) . . ? C32 C31 C30 120.4(4) . . ? C29 C30 C31 119.4(5) . . ? C30 C29 C28 121.1(5) . . ? F1 C33 C28 116.6(4) . . ? F1 C33 C32 119.1(5) . . ? C32 C33 C28 124.3(5) . . ? 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 F1 C33 1.331(5) . ? O1 C24 1.354(4) . ? N1 C27 1.270(4) . ? N1 C28 1.420(4) . ? C1 C2 1.388(5) . ? C1 C6 1.394(4) . ? C1 C7 1.493(4) . ? C2 C3 1.393(6) . ? C3 C4 1.377(7) . ? C4 C5 1.351(7) . ? C5 C6 1.373(5) . ? C7 C8 1.348(4) . ? C7 C21 1.501(4) . ? C8 C9 1.490(4) . ? C8 C15 1.499(4) . ? C9 C10 1.383(4) . ? C9 C14 1.399(4) . ? C10 C11 1.386(4) . ? C11 C12 1.364(5) . ? C12 C13 1.368(5) . ? C13 C14 1.377(4) . ? C15 C16 1.382(5) . ? C15 C20 1.374(5) . ? C16 C17 1.379(6) . ? C17 C18 1.341(7) . ? C18 C19 1.377(7) . ? C19 C20 1.393(5) . ? C21 C22 1.373(4) . ? C21 C26 1.403(4) . ? C22 C23 1.399(4) . ? C23 C24 1.406(4) . ? C23 C27 1.441(4) . ? C24 C25 1.375(5) . ? C25 C26 1.366(5) . ? C28 C29 1.385(6) . ? C28 C33 1.370(5) . ? C32 C31 1.361(8) . ? C32 C33 1.342(6) . ? C31 C30 1.393(8) . ? C30 C29 1.357(6) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 N1 0.82 1.91 2.633(4) 145.9 . 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 O1 C24 C25 C26 -178.2(4) . . . . ? N1 C28 C29 C30 175.8(4) . . . . ? N1 C28 C33 F1 -0.2(5) . . . . ? N1 C28 C33 C32 -179.6(4) . . . . ? C1 C2 C3 C4 -1.3(5) . . . . ? C1 C7 C8 C9 -10.9(4) . . . . ? C1 C7 C8 C15 167.2(3) . . . . ? C1 C7 C21 C22 -44.1(4) . . . . ? C1 C7 C21 C26 135.3(3) . . . . ? C2 C1 C6 C5 -0.6(5) . . . . ? C2 C1 C7 C8 131.8(3) . . . . ? C2 C1 C7 C21 -50.9(4) . . . . ? C2 C3 C4 C5 0.0(6) . . . . ? C3 C4 C5 C6 1.1(6) . . . . ? C4 C5 C6 C1 -0.8(6) . . . . ? C6 C1 C2 C3 1.6(5) . . . . ? C6 C1 C7 C8 -49.9(4) . . . . ? C6 C1 C7 C21 127.4(3) . . . . ? C7 C1 C2 C3 180.0(3) . . . . ? C7 C1 C6 C5 -178.9(3) . . . . ? C7 C8 C9 C10 -44.4(4) . . . . ? C7 C8 C9 C14 138.3(3) . . . . ? C7 C8 C15 C16 -58.4(4) . . . . ? C7 C8 C15 C20 125.3(3) . . . . ? C7 C21 C22 C23 -177.5(3) . . . . ? C7 C21 C26 C25 177.6(4) . . . . ? C8 C7 C21 C22 133.2(3) . . . . ? C8 C7 C21 C26 -47.3(4) . . . . ? C8 C9 C10 C11 -178.1(3) . . . . ? C8 C9 C14 C13 178.4(3) . . . . ? C8 C15 C16 C17 -176.6(3) . . . . ? C8 C15 C20 C19 177.4(3) . . . . ? C9 C8 C15 C16 119.8(3) . . . . ? C9 C8 C15 C20 -56.5(4) . . . . ? C9 C10 C11 C12 0.7(5) . . . . ? C10 C9 C14 C13 0.9(5) . . . . ? C10 C11 C12 C13 -0.8(5) . . . . ? C11 C12 C13 C14 0.9(5) . . . . ? C12 C13 C14 C9 -1.0(5) . . . . ? C14 C9 C10 C11 -0.8(4) . . . . ? C15 C8 C9 C10 137.3(3) . . . . ? C15 C8 C9 C14 -40.0(4) . . . . ? C15 C16 C17 C18 -0.1(6) . . . . ? C16 C15 C20 C19 1.1(5) . . . . ? C16 C17 C18 C19 -0.4(7) . . . . ? C17 C18 C19 C20 1.2(6) . . . . ? C18 C19 C20 C15 -1.6(6) . . . . ? C20 C15 C16 C17 -0.2(5) . . . . ? C21 C7 C8 C9 171.9(3) . . . . ? C21 C7 C8 C15 -10.0(4) . . . . ? C21 C22 C23 C24 -1.5(5) . . . . ? C21 C22 C23 C27 178.9(3) . . . . ? C22 C21 C26 C25 -3.0(5) . . . . ? C22 C23 C24 O1 178.3(4) . . . . ? C22 C23 C24 C25 -0.4(6) . . . . ? C22 C23 C27 N1 -176.4(3) . . . . ? C23 C24 C25 C26 0.5(6) . . . . ? C24 C23 C27 N1 4.0(6) . . . . ? C24 C25 C26 C21 1.2(6) . . . . ? C26 C21 C22 C23 3.1(5) . . . . ? C27 N1 C28 C29 62.9(5) . . . . ? C27 N1 C28 C33 -120.6(4) . . . . ? C27 C23 C24 O1 -2.1(6) . . . . ? C27 C23 C24 C25 179.2(4) . . . . ? C28 N1 C27 C23 -177.9(3) . . . . ? C32 C31 C30 C29 0.1(8) . . . . ? C31 C32 C33 F1 -174.4(4) . . . . ? C31 C32 C33 C28 5.0(8) . . . . ? C31 C30 C29 C28 2.1(7) . . . . ? C29 C28 C33 F1 176.6(4) . . . . ? C29 C28 C33 C32 -2.9(6) . . . . ? C33 C28 C29 C30 -0.8(6) . . . . ? C33 C32 C31 C30 -3.5(8) . . . . ?