#------------------------------------------------------------------------------ #$Date: 2020-05-27 06:34:59 +0300 (Wed, 27 May 2020) $ #$Revision: 252368 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157514.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_7157514 loop_ _publ_author_name 'Sugiura, Shinya' 'Maeda, Hiromitsu' _publ_section_title ; Pyrrole-based anion-responsive \p-electronic molecules as fluorescence sensors responsive to multiple stimuli ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00952K _journal_year 2020 _chemical_formula_moiety 'C51 H43 B F2 N4 O2, 2(C4 H8 O2)' _chemical_formula_sum 'C59 H59 B F2 N4 O6' _chemical_formula_weight 968.91 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2020-04-03 deposited with the CCDC. 2020-05-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 132.480(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 27.487(2) _cell_length_b 11.9733(10) _cell_length_c 19.9835(17) _cell_measurement_reflns_used 71568 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 15.497 _cell_measurement_theta_min 1.144 _cell_volume 4850.5(10) _computing_cell_refinement 'Rapid Auto(Rigaku)' _computing_data_collection 'Rapid Auto(Rigaku)' _computing_data_reduction 'Rapid Auto(Rigaku)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean 5.814 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Pilatus3 CdTe 1M' _diffrn_measurement_method \w _diffrn_radiation_type Synchrotron _diffrn_radiation_wavelength 0.4115 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_unetI/netI 0.0235 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 71568 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 14.294 _diffrn_reflns_theta_max 15.497 _diffrn_reflns_theta_min 1.144 _diffrn_source 'BL02B1 beamline SPring-8' _exptl_absorpt_coefficient_mu 0.038 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.7509 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; PROCESS-AUTO (1998). Automatic Data Acquisition and Processing Package for 2D image data. Rigaku Corporation, Tokyo, Japan. ; _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.327 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 2048 _exptl_crystal_size_max 1.000 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.050 _refine_diff_density_max 0.390 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 330 _refine_ls_number_reflns 5577 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0385 _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^)+(0.0495P)^2^+3.0611P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1017 _refine_ls_wR_factor_ref 0.1046 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5040 _reflns_number_total 5577 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00952k2.cif _cod_data_source_block ss-7-1 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_cell_volume 4850.4(9) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 7157514 _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 ; ss-7-1.res created by SHELXL-2014/7 TITL ss-7-1_a.res in C2/c REM Yadorkari-X generated CELL 0.41150 27.4868 11.9733 19.9835 90.0000 132.4800 90.0000 ZERR 4.0 0.0023 0.0010 0.0017 0.0000 0.0090 0.0000 LATT 7 SYMM -X, +Y, 1/2-Z REM SPGR C2/c monoclinic SFAC C H O N B F DISP C -0.00010 0.00047 5.15 DISP H 0.00000 0.00000 0.64 DISP O 0.00166 0.00180 10.17 DISP N 0.00042 0.00097 7.20 DISP B -0.00007 0.00019 3.72 DISP F 0.00375 0.00310 14.28 UNIT 236 236 24 16 4 8 TEMP -173.0 L.S. 30 FMAP 2 PLAN -20 ACTA CONF LIST 4 BOND $H WGHT 0.049500 3.061100 FVAR 0.59932 C1 1 0.720410 0.562897 0.374727 11.00000 0.01805 0.02230 = 0.01977 -0.00046 0.01176 -0.00110 C2 1 0.703806 0.675735 0.351617 11.00000 0.01928 0.02140 = 0.01964 -0.00023 0.01249 -0.00099 C3 1 0.636870 0.687554 0.308227 11.00000 0.01964 0.01990 = 0.01849 -0.00071 0.01226 -0.00108 C4 1 0.614673 0.581214 0.307317 11.00000 0.01823 0.01951 = 0.01930 0.00040 0.01199 0.00115 C5 1 0.554421 0.535364 0.277163 11.00000 0.02109 0.01765 = 0.01979 -0.00040 0.01332 -0.00080 C6 1 0.500000 0.594448 0.250000 10.50000 0.02114 0.01787 = 0.02208 0.00000 0.01440 0.00000 AFIX 43 H6 2 0.499999 0.673791 0.249998 10.50000 -1.20000 AFIX 0 C7 1 0.780994 0.501222 0.414714 11.00000 0.01778 0.02328 = 0.02351 -0.00442 0.01104 -0.00159 C8 1 0.802850 0.415555 0.476954 11.00000 0.02460 0.02769 = 0.02819 0.00045 0.01306 0.00273 AFIX 43 H8 2 0.780292 0.401259 0.496779 11.00000 -1.20000 AFIX 0 C9 1 0.857015 0.351240 0.510085 11.00000 0.02559 0.02948 = 0.03541 -0.00209 0.00919 0.00572 AFIX 43 H9 2 0.871956 0.294033 0.553211 11.00000 -1.20000 AFIX 0 C10 1 0.889178 0.370408 0.480360 11.00000 0.01971 0.03471 = 0.05006 -0.01461 0.01411 0.00213 AFIX 43 H10 2 0.925756 0.325244 0.502052 11.00000 -1.20000 AFIX 0 C11 1 0.868437 0.455125 0.419075 11.00000 0.02553 0.04005 = 0.04997 -0.01929 0.02500 -0.00812 AFIX 43 H11 2 0.890812 0.467822 0.398787 11.00000 -1.20000 AFIX 0 C12 1 0.815048 0.521836 0.386960 11.00000 0.02254 0.03065 = 0.03396 -0.00866 0.01830 -0.00529 AFIX 43 H12 2 0.801776 0.581331 0.346206 11.00000 -1.20000 AFIX 0 C13 1 0.750751 0.762182 0.372200 11.00000 0.01970 0.02013 = 0.02295 -0.00047 0.01388 -0.00080 C14 1 0.806842 0.786343 0.461780 11.00000 0.02531 0.02742 = 0.02119 0.00041 0.01548 -0.00402 AFIX 43 H14 2 0.812933 0.750084 0.509269 11.00000 -1.20000 AFIX 0 C15 1 0.853997 0.861543 0.483784 11.00000 0.02303 0.02850 = 0.01998 -0.00183 0.01283 -0.00449 AFIX 43 H15 2 0.891296 0.876630 0.545756 11.00000 -1.20000 AFIX 0 C16 1 0.847546 0.915734 0.416048 11.00000 0.02341 0.02133 = 0.02516 -0.00105 0.01680 -0.00187 C17 1 0.790686 0.892637 0.325696 11.00000 0.02758 0.02521 = 0.02312 0.00205 0.01725 -0.00156 AFIX 43 H17 2 0.784391 0.928717 0.277993 11.00000 -1.20000 AFIX 0 C18 1 0.743520 0.818047 0.304834 11.00000 0.02211 0.02542 = 0.02004 -0.00033 0.01186 -0.00179 AFIX 43 H18 2 0.705301 0.804726 0.243005 11.00000 -1.20000 AFIX 0 C19 1 0.945520 1.027096 0.529911 11.00000 0.03864 0.04794 = 0.03024 -0.00429 0.01811 -0.02275 AFIX 137 H19 2 0.923971 1.072343 0.544421 11.00000 -1.50000 H19A 2 0.978123 1.072722 0.536454 11.00000 -1.50000 H19B 2 0.967629 0.963299 0.571444 11.00000 -1.50000 AFIX 0 C20 1 0.880262 1.064234 0.368926 11.00000 0.03980 0.03058 = 0.03561 0.00041 0.02787 -0.00804 AFIX 137 H20 2 0.866203 1.022202 0.316277 11.00000 -1.50000 H20A 2 0.919164 1.109161 0.393973 11.00000 -1.50000 H20B 2 0.844426 1.113497 0.350206 11.00000 -1.50000 AFIX 0 C21 1 0.598498 0.792364 0.268886 11.00000 0.02073 0.02021 = 0.02330 0.00226 0.01514 0.00023 C22 1 0.622278 0.890675 0.319889 11.00000 0.02343 0.02220 = 0.02511 0.00018 0.01486 -0.00102 AFIX 43 H22 2 0.663319 0.890044 0.380958 11.00000 -1.20000 AFIX 0 C23 1 0.586583 0.989110 0.282267 11.00000 0.03143 0.02014 = 0.03469 -0.00031 0.02232 -0.00097 AFIX 43 H23 2 0.603126 1.055221 0.317865 11.00000 -1.20000 AFIX 0 C24 1 0.526971 0.991697 0.193136 11.00000 0.02969 0.02300 = 0.03674 0.00784 0.02172 0.00590 AFIX 43 H24 2 0.502604 1.059296 0.167588 11.00000 -1.20000 AFIX 0 C25 1 0.503046 0.895139 0.141400 11.00000 0.02481 0.03022 = 0.02626 0.00634 0.01333 0.00340 AFIX 43 H25 2 0.462215 0.896529 0.080156 11.00000 -1.20000 AFIX 0 C26 1 0.538643 0.796358 0.178908 11.00000 0.02425 0.02347 = 0.02399 0.00006 0.01444 -0.00098 AFIX 43 H26 2 0.522032 0.730643 0.142845 11.00000 -1.20000 AFIX 0 C27 1 0.749814 0.123593 0.388802 11.00000 0.04760 0.03248 = 0.08607 0.00581 0.04988 0.00835 AFIX 137 H27 2 0.775337 0.141653 0.452729 11.00000 -1.50000 H27A 2 0.777451 0.134353 0.374758 11.00000 -1.50000 H27B 2 0.735228 0.045642 0.377412 11.00000 -1.50000 AFIX 0 C28 1 0.691044 0.198445 0.330158 11.00000 0.04429 0.02306 = 0.07076 0.00225 0.04590 0.00036 C29 1 0.598538 0.250595 0.178985 11.00000 0.05071 0.02948 = 0.06883 0.00409 0.04914 0.00572 AFIX 23 H29 2 0.610397 0.330378 0.185055 11.00000 -1.20000 H29A 2 0.569404 0.242620 0.191394 11.00000 -1.20000 AFIX 0 C30 1 0.564136 0.209797 0.085419 11.00000 0.05278 0.03637 = 0.07235 -0.00322 0.05055 -0.00174 AFIX 137 H30 2 0.594869 0.211105 0.076122 11.00000 -1.50000 H30A 2 0.526414 0.258337 0.040641 11.00000 -1.50000 H30B 2 0.548602 0.133239 0.078240 11.00000 -1.50000 AFIX 0 N1 4 0.666632 0.508276 0.347983 11.00000 0.01899 0.01815 = 0.02301 0.00112 0.01343 0.00026 AFIX 43 H1 2 0.665094 0.436364 0.355516 11.00000 -1.20000 AFIX 0 N2 4 0.896519 0.987089 0.437439 11.00000 0.03049 0.03088 = 0.02673 -0.00161 0.01838 -0.01059 O1 3 0.555769 0.425304 0.280083 11.00000 0.02389 0.01666 = 0.05086 0.00109 0.02481 0.00044 O2 3 0.674887 0.264696 0.358029 11.00000 0.04307 0.02407 = 0.06546 -0.00095 0.04099 0.00195 O3 3 0.657683 0.183313 0.242375 11.00000 0.05380 0.03200 = 0.07199 0.00517 0.05270 0.00813 B1 5 0.500000 0.355730 0.250000 10.50000 0.02109 0.01767 = 0.03035 0.00000 0.01685 0.00000 F1 6 0.480054 0.290387 0.179166 11.00000 0.02735 0.05136 = 0.03952 -0.01927 0.02081 -0.00555 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM ss-7-1_a.res in C2/c REM R1 = 0.0385 for 5040 Fo > 4sig(Fo) and 0.0420 for all 5577 data REM 330 parameters refined using 0 restraints END WGHT 0.0495 3.0610 REM Highest difference peak 0.390, deepest hole -0.294, 1-sigma level 0.041 Q1 1 0.5000 0.2626 0.2500 10.50000 0.05 0.39 Q2 1 0.7175 0.6216 0.3666 11.00000 0.05 0.25 Q3 1 0.7256 0.7207 0.3627 11.00000 0.05 0.23 Q4 1 0.7799 0.7720 0.4126 11.00000 0.05 0.22 Q5 1 0.6714 0.6899 0.3345 11.00000 0.05 0.22 Q6 1 0.9687 1.1392 0.6302 11.00000 0.05 0.22 Q7 1 0.6184 0.6333 0.3026 11.00000 0.05 0.22 Q8 1 0.5693 0.7932 0.2277 11.00000 0.05 0.22 Q9 1 0.6183 0.7381 0.2915 11.00000 0.05 0.21 Q10 1 0.7421 0.8031 0.3419 11.00000 0.05 0.20 Q11 1 0.7514 0.5390 0.3986 11.00000 0.05 0.19 Q12 1 0.5597 0.9861 0.2372 11.00000 0.05 0.19 Q13 1 0.5849 0.5686 0.2927 11.00000 0.05 0.19 Q14 1 0.7962 0.5078 0.4018 11.00000 0.05 0.18 Q15 1 0.6393 0.5484 0.3283 11.00000 0.05 0.18 Q16 1 0.6053 0.9384 0.2962 11.00000 0.05 0.18 Q17 1 0.6126 0.8398 0.2914 11.00000 0.05 0.17 Q18 1 0.5268 0.5682 0.2733 11.00000 0.05 0.16 Q19 1 0.5209 0.8487 0.1636 11.00000 0.05 0.16 Q20 1 0.7850 0.4486 0.4298 11.00000 0.05 0.16 ; _shelx_res_checksum 87348 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -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 C1 C 0.72041(5) 0.56290(9) 0.37473(7) 0.0209(2) Uani 1 1 d . . . . . C2 C 0.70381(5) 0.67573(9) 0.35162(7) 0.0207(2) Uani 1 1 d . . . . . C3 C 0.63687(5) 0.68755(8) 0.30823(7) 0.0198(2) Uani 1 1 d . . . . . C4 C 0.61467(5) 0.58121(8) 0.30732(7) 0.0196(2) Uani 1 1 d . . . . . C5 C 0.55442(5) 0.53536(8) 0.27716(7) 0.0199(2) Uani 1 1 d . . . . . C6 C 0.5000 0.59445(12) 0.2500 0.0205(3) Uani 1 2 d S T P . . H6 H 0.5000 0.6738 0.2500 0.025 Uiso 1 2 calc R U P . . C7 C 0.78099(5) 0.50122(9) 0.41471(7) 0.0239(2) Uani 1 1 d . . . . . C8 C 0.80285(6) 0.41556(10) 0.47695(8) 0.0308(2) Uani 1 1 d . . . . . H8 H 0.7803 0.4013 0.4968 0.037 Uiso 1 1 calc R U . . . C9 C 0.85702(6) 0.35124(11) 0.51008(9) 0.0396(3) Uani 1 1 d . . . . . H9 H 0.8720 0.2940 0.5532 0.048 Uiso 1 1 calc R U . . . C10 C 0.88918(6) 0.37041(11) 0.48036(10) 0.0427(3) Uani 1 1 d . . . . . H10 H 0.9258 0.3252 0.5021 0.051 Uiso 1 1 calc R U . . . C11 C 0.86844(6) 0.45513(12) 0.41907(10) 0.0389(3) Uani 1 1 d . . . . . H11 H 0.8908 0.4678 0.3988 0.047 Uiso 1 1 calc R U . . . C12 C 0.81505(6) 0.52184(10) 0.38696(8) 0.0297(2) Uani 1 1 d . . . . . H12 H 0.8018 0.5813 0.3462 0.036 Uiso 1 1 calc R U . . . C13 C 0.75075(5) 0.76218(9) 0.37220(7) 0.0214(2) Uani 1 1 d . . . . . C14 C 0.80684(5) 0.78634(9) 0.46178(7) 0.0248(2) Uani 1 1 d . . . . . H14 H 0.8129 0.7501 0.5093 0.030 Uiso 1 1 calc R U . . . C15 C 0.85400(5) 0.86154(9) 0.48378(7) 0.0252(2) Uani 1 1 d . . . . . H15 H 0.8913 0.8766 0.5458 0.030 Uiso 1 1 calc R U . . . C16 C 0.84755(5) 0.91573(9) 0.41605(7) 0.0230(2) Uani 1 1 d . . . . . C17 C 0.79069(5) 0.89264(9) 0.32570(7) 0.0252(2) Uani 1 1 d . . . . . H17 H 0.7844 0.9287 0.2780 0.030 Uiso 1 1 calc R U . . . C18 C 0.74352(5) 0.81805(9) 0.30483(7) 0.0245(2) Uani 1 1 d . . . . . H18 H 0.7053 0.8047 0.2430 0.029 Uiso 1 1 calc R U . . . C19 C 0.94552(7) 1.02710(13) 0.52991(9) 0.0432(3) Uani 1 1 d . . . . . H19 H 0.9240 1.0723 0.5444 0.065 Uiso 1 1 calc R U . . . H19A H 0.9781 1.0727 0.5365 0.065 Uiso 1 1 calc R U . . . H19B H 0.9676 0.9633 0.5714 0.065 Uiso 1 1 calc R U . . . C20 C 0.88026(7) 1.06423(10) 0.36893(9) 0.0333(3) Uani 1 1 d . . . . . H20 H 0.8662 1.0222 0.3163 0.050 Uiso 1 1 calc R U . . . H20A H 0.9192 1.1092 0.3940 0.050 Uiso 1 1 calc R U . . . H20B H 0.8444 1.1135 0.3502 0.050 Uiso 1 1 calc R U . . . C21 C 0.59850(5) 0.79236(9) 0.26889(7) 0.0212(2) Uani 1 1 d . . . . . C22 C 0.62228(5) 0.89067(9) 0.31989(7) 0.0248(2) Uani 1 1 d . . . . . H22 H 0.6633 0.8900 0.3810 0.030 Uiso 1 1 calc R U . . . C23 C 0.58658(6) 0.98911(9) 0.28227(8) 0.0288(2) Uani 1 1 d . . . . . H23 H 0.6031 1.0552 0.3179 0.035 Uiso 1 1 calc R U . . . C24 C 0.52697(6) 0.99170(10) 0.19314(8) 0.0304(2) Uani 1 1 d . . . . . H24 H 0.5026 1.0593 0.1676 0.036 Uiso 1 1 calc R U . . . C25 C 0.50305(6) 0.89514(10) 0.14140(8) 0.0303(2) Uani 1 1 d . . . . . H25 H 0.4622 0.8965 0.0802 0.036 Uiso 1 1 calc R U . . . C26 C 0.53864(5) 0.79636(9) 0.17891(7) 0.0254(2) Uani 1 1 d . . . . . H26 H 0.5220 0.7306 0.1428 0.031 Uiso 1 1 calc R U . . . C27 C 0.74981(8) 0.12359(12) 0.38880(13) 0.0515(4) Uani 1 1 d . . . . . H27 H 0.7753 0.1417 0.4527 0.077 Uiso 1 1 calc R U . . . H27A H 0.7775 0.1344 0.3748 0.077 Uiso 1 1 calc R U . . . H27B H 0.7352 0.0456 0.3774 0.077 Uiso 1 1 calc R U . . . C28 C 0.69104(7) 0.19845(10) 0.33016(11) 0.0402(3) Uani 1 1 d . . . . . C29 C 0.59854(7) 0.25060(12) 0.17899(11) 0.0424(3) Uani 1 1 d . . . . . H29 H 0.6104 0.3304 0.1851 0.051 Uiso 1 1 calc R U . . . H29A H 0.5694 0.2426 0.1914 0.051 Uiso 1 1 calc R U . . . C30 C 0.56414(8) 0.20980(12) 0.08542(12) 0.0470(4) Uani 1 1 d . . . . . H30 H 0.5949 0.2111 0.0761 0.070 Uiso 1 1 calc R U . . . H30A H 0.5264 0.2583 0.0406 0.070 Uiso 1 1 calc R U . . . H30B H 0.5486 0.1332 0.0782 0.070 Uiso 1 1 calc R U . . . N1 N 0.66663(4) 0.50828(7) 0.34798(6) 0.02068(18) Uani 1 1 d . . . . . H1 H 0.6651 0.4364 0.3555 0.025 Uiso 1 1 calc R U . . . N2 N 0.89652(5) 0.98709(9) 0.43744(7) 0.0301(2) Uani 1 1 d . . . . . O1 O 0.55577(4) 0.42530(6) 0.28008(6) 0.0308(2) Uani 1 1 d . . . . . O2 O 0.67489(5) 0.26470(7) 0.35803(7) 0.0406(2) Uani 1 1 d . . . . . O3 O 0.65768(5) 0.18331(8) 0.24238(8) 0.0441(2) Uani 1 1 d . . . . . B1 B 0.5000 0.35573(14) 0.2500 0.0235(3) Uani 1 2 d S T P . . F1 F 0.48005(4) 0.29039(7) 0.17917(5) 0.0409(2) 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 C1 0.0180(5) 0.0223(5) 0.0198(4) -0.0005(4) 0.0118(4) -0.0011(4) C2 0.0193(5) 0.0214(5) 0.0196(4) -0.0002(4) 0.0125(4) -0.0010(4) C3 0.0196(5) 0.0199(5) 0.0185(4) -0.0007(4) 0.0123(4) -0.0011(4) C4 0.0182(4) 0.0195(5) 0.0193(4) 0.0004(4) 0.0120(4) 0.0012(4) C5 0.0211(5) 0.0176(5) 0.0198(4) -0.0004(3) 0.0133(4) -0.0008(4) C6 0.0211(7) 0.0179(6) 0.0221(6) 0.000 0.0144(6) 0.000 C7 0.0178(5) 0.0233(5) 0.0235(5) -0.0044(4) 0.0110(4) -0.0016(4) C8 0.0246(5) 0.0277(6) 0.0282(5) 0.0005(4) 0.0131(5) 0.0027(4) C9 0.0256(6) 0.0295(6) 0.0354(6) -0.0021(5) 0.0092(5) 0.0057(5) C10 0.0197(5) 0.0347(7) 0.0501(8) -0.0146(6) 0.0141(6) 0.0021(5) C11 0.0255(6) 0.0400(7) 0.0500(8) -0.0193(6) 0.0250(6) -0.0081(5) C12 0.0225(5) 0.0306(6) 0.0340(6) -0.0087(5) 0.0183(5) -0.0053(4) C13 0.0197(5) 0.0201(5) 0.0229(5) -0.0005(4) 0.0139(4) -0.0008(4) C14 0.0253(5) 0.0274(5) 0.0212(5) 0.0004(4) 0.0155(4) -0.0040(4) C15 0.0230(5) 0.0285(5) 0.0200(5) -0.0018(4) 0.0128(4) -0.0045(4) C16 0.0234(5) 0.0213(5) 0.0252(5) -0.0010(4) 0.0168(4) -0.0019(4) C17 0.0276(5) 0.0252(5) 0.0231(5) 0.0020(4) 0.0173(5) -0.0016(4) C18 0.0221(5) 0.0254(5) 0.0200(5) -0.0003(4) 0.0119(4) -0.0018(4) C19 0.0386(7) 0.0479(8) 0.0302(6) -0.0043(6) 0.0181(6) -0.0228(6) C20 0.0398(7) 0.0306(6) 0.0356(6) 0.0004(5) 0.0279(6) -0.0080(5) C21 0.0207(5) 0.0202(5) 0.0233(5) 0.0023(4) 0.0151(4) 0.0002(4) C22 0.0234(5) 0.0222(5) 0.0251(5) 0.0002(4) 0.0149(4) -0.0010(4) C23 0.0314(6) 0.0201(5) 0.0347(6) -0.0003(4) 0.0223(5) -0.0010(4) C24 0.0297(6) 0.0230(5) 0.0367(6) 0.0078(4) 0.0217(5) 0.0059(4) C25 0.0248(5) 0.0302(6) 0.0263(5) 0.0063(4) 0.0133(5) 0.0034(4) C26 0.0242(5) 0.0235(5) 0.0240(5) 0.0001(4) 0.0144(4) -0.0010(4) C27 0.0476(8) 0.0325(7) 0.0861(12) 0.0058(7) 0.0499(9) 0.0083(6) C28 0.0443(7) 0.0231(6) 0.0708(10) 0.0023(6) 0.0459(8) 0.0004(5) C29 0.0507(8) 0.0295(6) 0.0688(10) 0.0041(6) 0.0491(8) 0.0057(6) C30 0.0528(8) 0.0364(7) 0.0724(10) -0.0032(7) 0.0506(8) -0.0017(6) N1 0.0190(4) 0.0181(4) 0.0230(4) 0.0011(3) 0.0134(4) 0.0003(3) N2 0.0305(5) 0.0309(5) 0.0267(5) -0.0016(4) 0.0184(4) -0.0106(4) O1 0.0239(4) 0.0167(4) 0.0509(5) 0.0011(3) 0.0248(4) 0.0004(3) O2 0.0431(5) 0.0241(4) 0.0655(6) -0.0009(4) 0.0410(5) 0.0019(4) O3 0.0538(6) 0.0320(5) 0.0720(7) 0.0052(5) 0.0527(6) 0.0081(4) B1 0.0211(7) 0.0177(7) 0.0304(8) 0.000 0.0168(7) 0.000 F1 0.0273(4) 0.0514(5) 0.0395(4) -0.0193(3) 0.0208(3) -0.0056(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C -0.0001 0.0005 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0017 0.0018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0004 0.0010 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B -0.0001 0.0002 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0037 0.0031 '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 N1 C1 C2 108.07(9) . . ? N1 C1 C7 120.42(9) . . ? C2 C1 C7 131.39(9) . . ? C1 C2 C3 107.33(9) . . ? C1 C2 C13 123.66(9) . . ? C3 C2 C13 129.01(9) . . ? C4 C3 C2 106.89(9) . . ? C4 C3 C21 127.88(9) . . ? C2 C3 C21 125.19(9) . . ? N1 C4 C3 107.37(9) . . ? N1 C4 C5 116.63(9) . . ? C3 C4 C5 135.99(9) . . ? O1 C5 C6 121.07(10) . . ? O1 C5 C4 111.95(9) . . ? C6 C5 C4 126.95(10) . . ? C5 C6 C5 118.88(13) . 2_655 ? C5 C6 H6 120.6 . . ? C5 C6 H6 120.6 2_655 . ? C12 C7 C8 118.91(11) . . ? C12 C7 C1 120.87(10) . . ? C8 C7 C1 120.08(10) . . ? C9 C8 C7 120.75(12) . . ? C9 C8 H8 119.6 . . ? C7 C8 H8 119.6 . . ? C10 C9 C8 119.82(13) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 120.24(12) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 120.40(13) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C7 119.84(12) . . ? C11 C12 H12 120.1 . . ? C7 C12 H12 120.1 . . ? C14 C13 C18 117.04(10) . . ? C14 C13 C2 120.24(9) . . ? C18 C13 C2 122.63(9) . . ? C15 C14 C13 122.02(10) . . ? C15 C14 H14 119.0 . . ? C13 C14 H14 119.0 . . ? C14 C15 C16 120.96(10) . . ? C14 C15 H15 119.5 . . ? C16 C15 H15 119.5 . . ? N2 C16 C15 121.42(10) . . ? N2 C16 C17 121.38(10) . . ? C15 C16 C17 117.17(10) . . ? C18 C17 C16 121.12(10) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C17 C18 C13 121.66(10) . . ? C17 C18 H18 119.2 . . ? C13 C18 H18 119.2 . . ? N2 C19 H19 109.5 . . ? N2 C19 H19A 109.5 . . ? H19 C19 H19A 109.5 . . ? N2 C19 H19B 109.5 . . ? H19 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N2 C20 H20 109.5 . . ? N2 C20 H20A 109.5 . . ? H20 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? H20 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C26 C21 C22 118.35(10) . . ? C26 C21 C3 120.75(9) . . ? C22 C21 C3 120.86(9) . . ? C23 C22 C21 120.65(10) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 120.41(11) . . ? C24 C23 H23 119.8 . . ? C22 C23 H23 119.8 . . ? C23 C24 C25 119.63(11) . . ? C23 C24 H24 120.2 . . ? C25 C24 H24 120.2 . . ? C24 C25 C26 120.11(11) . . ? C24 C25 H25 119.9 . . ? C26 C25 H25 119.9 . . ? C25 C26 C21 120.85(10) . . ? C25 C26 H26 119.6 . . ? C21 C26 H26 119.6 . . ? C28 C27 H27 109.5 . . ? C28 C27 H27A 109.5 . . ? H27 C27 H27A 109.5 . . ? C28 C27 H27B 109.5 . . ? H27 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O2 C28 O3 123.59(13) . . ? O2 C28 C27 124.74(16) . . ? O3 C28 C27 111.67(13) . . ? O3 C29 C30 107.39(11) . . ? O3 C29 H29 110.2 . . ? C30 C29 H29 110.2 . . ? O3 C29 H29A 110.2 . . ? C30 C29 H29A 110.2 . . ? H29 C29 H29A 108.5 . . ? C29 C30 H30 109.5 . . ? C29 C30 H30A 109.5 . . ? H30 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C1 N1 C4 110.34(9) . . ? C1 N1 H1 124.8 . . ? C4 N1 H1 124.8 . . ? C16 N2 C19 117.83(10) . . ? C16 N2 C20 118.85(10) . . ? C19 N2 C20 114.98(10) . . ? C5 O1 B1 123.91(9) . . ? C28 O3 C29 116.21(11) . . ? F1 B1 F1 110.16(14) 2_655 . ? F1 B1 O1 108.83(5) 2_655 . ? F1 B1 O1 109.03(5) . . ? F1 B1 O1 109.03(5) 2_655 2_655 ? F1 B1 O1 108.83(5) . 2_655 ? O1 B1 O1 110.96(12) . 2_655 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.3533(13) . ? C1 C2 1.4008(14) . ? C1 C7 1.4696(14) . ? C2 C3 1.4150(14) . ? C2 C13 1.4794(14) . ? C3 C4 1.4067(14) . ? C3 C21 1.4783(14) . ? C4 N1 1.3767(13) . ? C4 C5 1.4350(14) . ? C5 O1 1.3185(13) . ? C5 C6 1.3914(12) . ? C6 C5 1.3914(12) 2_655 ? C6 H6 0.9500 . ? C7 C12 1.3949(16) . ? C7 C8 1.3967(16) . ? C8 C9 1.3844(17) . ? C8 H8 0.9500 . ? C9 C10 1.377(2) . ? C9 H9 0.9500 . ? C10 C11 1.382(2) . ? C10 H10 0.9500 . ? C11 C12 1.3897(17) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 C14 1.3919(15) . ? C13 C18 1.3921(15) . ? C14 C15 1.3836(15) . ? C14 H14 0.9500 . ? C15 C16 1.4002(15) . ? C15 H15 0.9500 . ? C16 N2 1.3955(14) . ? C16 C17 1.4027(15) . ? C17 C18 1.3864(15) . ? C17 H17 0.9500 . ? C18 H18 0.9500 . ? C19 N2 1.4480(16) . ? C19 H19 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C20 N2 1.4495(15) . ? C20 H20 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C21 C26 1.3952(15) . ? C21 C22 1.3971(15) . ? C22 C23 1.3859(15) . ? C22 H22 0.9500 . ? C23 C24 1.3843(17) . ? C23 H23 0.9500 . ? C24 C25 1.3855(17) . ? C24 H24 0.9500 . ? C25 C26 1.3883(16) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.493(2) . ? C27 H27 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C28 O2 1.2128(16) . ? C28 O3 1.3335(19) . ? C29 O3 1.4543(18) . ? C29 C30 1.497(2) . ? C29 H29 0.9900 . ? C29 H29A 0.9900 . ? C30 H30 0.9800 . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? N1 H1 0.8800 . ? O1 B1 1.4699(12) . ? B1 F1 1.3668(12) 2_655 ? B1 F1 1.3668(12) . ? B1 O1 1.4699(12) 2_655 ? 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 N1 C1 C2 C3 -0.77(11) . . . . ? C7 C1 C2 C3 175.08(10) . . . . ? N1 C1 C2 C13 178.53(9) . . . . ? C7 C1 C2 C13 -5.62(18) . . . . ? C1 C2 C3 C4 0.88(11) . . . . ? C13 C2 C3 C4 -178.38(10) . . . . ? C1 C2 C3 C21 -176.91(9) . . . . ? C13 C2 C3 C21 3.84(17) . . . . ? C2 C3 C4 N1 -0.66(11) . . . . ? C21 C3 C4 N1 177.04(9) . . . . ? C2 C3 C4 C5 177.84(11) . . . . ? C21 C3 C4 C5 -4.45(19) . . . . ? N1 C4 C5 O1 -10.73(13) . . . . ? C3 C4 C5 O1 170.86(11) . . . . ? N1 C4 C5 C6 167.26(8) . . . . ? C3 C4 C5 C6 -11.14(18) . . . . ? O1 C5 C6 C5 -2.10(7) . . . 2_655 ? C4 C5 C6 C5 -179.92(11) . . . 2_655 ? N1 C1 C7 C12 134.20(11) . . . . ? C2 C1 C7 C12 -41.23(17) . . . . ? N1 C1 C7 C8 -41.51(15) . . . . ? C2 C1 C7 C8 143.07(12) . . . . ? C12 C7 C8 C9 -0.61(17) . . . . ? C1 C7 C8 C9 175.18(11) . . . . ? C7 C8 C9 C10 -1.11(18) . . . . ? C8 C9 C10 C11 1.38(19) . . . . ? C9 C10 C11 C12 0.09(19) . . . . ? C10 C11 C12 C7 -1.83(18) . . . . ? C8 C7 C12 C11 2.06(16) . . . . ? C1 C7 C12 C11 -173.69(10) . . . . ? C1 C2 C13 C14 -62.33(15) . . . . ? C3 C2 C13 C14 116.82(12) . . . . ? C1 C2 C13 C18 114.02(12) . . . . ? C3 C2 C13 C18 -66.84(15) . . . . ? C18 C13 C14 C15 -0.62(17) . . . . ? C2 C13 C14 C15 175.93(10) . . . . ? C13 C14 C15 C16 -0.92(18) . . . . ? C14 C15 C16 N2 -176.48(11) . . . . ? C14 C15 C16 C17 1.64(17) . . . . ? N2 C16 C17 C18 177.25(11) . . . . ? C15 C16 C17 C18 -0.87(16) . . . . ? C16 C17 C18 C13 -0.67(17) . . . . ? C14 C13 C18 C17 1.40(16) . . . . ? C2 C13 C18 C17 -175.06(10) . . . . ? C4 C3 C21 C26 -51.39(15) . . . . ? C2 C3 C21 C26 125.93(11) . . . . ? C4 C3 C21 C22 130.75(11) . . . . ? C2 C3 C21 C22 -51.94(15) . . . . ? C26 C21 C22 C23 1.11(16) . . . . ? C3 C21 C22 C23 179.03(10) . . . . ? C21 C22 C23 C24 -0.57(18) . . . . ? C22 C23 C24 C25 -0.08(18) . . . . ? C23 C24 C25 C26 0.15(19) . . . . ? C24 C25 C26 C21 0.42(18) . . . . ? C22 C21 C26 C25 -1.04(16) . . . . ? C3 C21 C26 C25 -178.96(10) . . . . ? C2 C1 N1 C4 0.36(11) . . . . ? C7 C1 N1 C4 -176.03(9) . . . . ? C3 C4 N1 C1 0.20(11) . . . . ? C5 C4 N1 C1 -178.64(9) . . . . ? C15 C16 N2 C19 -16.03(17) . . . . ? C17 C16 N2 C19 165.93(12) . . . . ? C15 C16 N2 C20 -162.76(11) . . . . ? C17 C16 N2 C20 19.20(17) . . . . ? C6 C5 O1 B1 4.24(14) . . . . ? C4 C5 O1 B1 -177.64(7) . . . . ? O2 C28 O3 C29 -0.86(18) . . . . ? C27 C28 O3 C29 178.74(11) . . . . ? C30 C29 O3 C28 -172.38(11) . . . . ? C5 O1 B1 F1 -122.11(12) . . . 2_655 ? C5 O1 B1 F1 117.70(12) . . . . ? C5 O1 B1 O1 -2.14(7) . . . 2_655 ?