#------------------------------------------------------------------------------ #$Date: 2023-03-04 20:44:28 +0200 (Sat, 04 Mar 2023) $ #$Revision: 281594 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159118.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_7159118 loop_ _publ_author_name F e r r e i r a , ; ; J o a n a ; ; R ; ; M | ; ; A l v e s , ; ; M a r i a n a | ; ; S o u s a , ; ; B & '#' x e 1 ; r b a r a | ; ; V i e i r a , ; ; S a n d r a ; ; I | ; ; S i l v a , ; ; A r t u r ; ; M ; ; S | ; ; G u i e u , ; ; S a m u e l | ; ; C u n h a , ; ; & '#' x c 2 ; n g e l a | ; ; N u n e s ; ; d a ; ; S i l v a , ; ; R a q u e l _publ_section_title ; Curcumin-based molecular probes for fluorescence imaging of fungi. ; _journal_issue 7 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 1531 _journal_page_last 1536 _journal_paper_doi 10.1039/d2ob01872a _journal_volume 21 _journal_year 2023 _chemical_formula_sum 'C23 H23 B F2 O4.5' _chemical_formula_weight 420.22 _chemical_name_systematic 2,2-difluoro-4,6-bis((E)-4-methoxystyryl)-2H-1l3,3,2l4-dioxaborinine _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2022-03-23 deposited with the CCDC. 2023-01-11 downloaded from the CCDC. ; _cell_angle_alpha 66.33(5) _cell_angle_beta 75.73(7) _cell_angle_gamma 85.18(5) _cell_formula_units_Z 2 _cell_length_a 8.84(2) _cell_length_b 10.70(3) _cell_length_c 11.53(3) _cell_measurement_reflns_used 2723 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.43 _cell_measurement_theta_min 2.20 _cell_volume 968(4) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL-2014 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXL-2014 (Sheldrick, 2014)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type ccd _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_unetI/netI 0.0694 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 11794 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 28.792 _diffrn_reflns_theta_min 2.079 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.111 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _exptl_crystal_colour purple _exptl_crystal_density_diffrn 1.442 _exptl_crystal_description flake _exptl_crystal_F_000 440 _exptl_crystal_preparation Luminescent _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: tetrahydrofuran' _exptl_crystal_size_max 0.700 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_min 0.150 _exptl_transmission_factor_max 0.7457 _exptl_transmission_factor_min 0.5588 _refine_diff_density_max 0.245 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 282 _refine_ls_number_reflns 4937 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.023 _refine_ls_R_factor_all 0.0894 _refine_ls_R_factor_gt 0.0543 _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^)+(0.0566P)^2^+0.2084P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1264 _refine_ls_wR_factor_ref 0.1442 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3272 _reflns_number_total 4937 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d2ob01872a2.cif _cod_data_source_block shelx_CCDC1 _cod_depositor_comments 'Adding full bibliography for 7159117--7159118.cif.' _cod_original_formula_sum 'C23 H23 B F2 O4.50' _cod_database_code 7159118 _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. ; _shelx_estimated_absorpt_t_min 0.927 _shelx_estimated_absorpt_t_max 0.984 _shelx_res_file ; TITL purple_a.res in P-1 shelx.res created by SHELXL-2018/3 at 13:33:55 on 03-Feb-2022 CELL 0.71073 8.8413 10.6994 11.5276 66.327 75.730 85.181 ZERR 2.00 0.0215 0.0252 0.0276 0.054 0.065 0.049 LATT 1 SFAC C H O B F UNIT 46 46 9 2 4 MERG 2 EQIV $1 x+1, y-1, z HTAB C21 F2_$1 EQIV $2 -x+1, -y+1, -z+1 HTAB C13 F1_$2 EQIV $3 -x, -y+2, -z+1 HTAB C01 F2_$3 HTAB C21 F2_$1 HTAB C13 F1_$2 HTAB C01 F2_$3 FMAP 2 PLAN 20 SIZE 0.150 0.500 0.700 ACTA BOND $H CONF L.S. 99 TEMP -123.00 WGHT 0.056600 0.208400 FVAR 0.13479 F1 5 0.290741 0.631673 0.326268 11.00000 0.03095 0.03807 = 0.03853 -0.01770 -0.01112 -0.00066 F2 5 0.408247 0.820680 0.166982 11.00000 0.03572 0.03565 = 0.03214 -0.01384 -0.01166 0.00723 O04 3 1.299000 0.152521 0.215943 11.00000 0.03447 0.03787 = 0.04272 -0.02332 -0.01781 0.01906 O01 3 0.067806 1.163311 0.898147 11.00000 0.02461 0.04195 = 0.03589 -0.02627 -0.01090 0.01108 O03 3 0.556979 0.656952 0.283367 11.00000 0.02814 0.03965 = 0.03587 -0.02439 -0.01522 0.01195 O02 3 0.379790 0.792093 0.379695 11.00000 0.02657 0.03781 = 0.03656 -0.02325 -0.01434 0.01078 C21 1 1.339079 0.126869 0.100671 11.00000 0.03752 0.04474 = 0.05024 -0.03340 -0.01728 0.01982 AFIX 137 H21A 2 1.251848 0.079714 0.095954 11.00000 -1.50000 H21C 2 1.431655 0.069581 0.101752 11.00000 -1.50000 H21B 2 1.361432 0.213586 0.024648 11.00000 -1.50000 AFIX 0 C18 1 1.177299 0.234372 0.227083 11.00000 0.02335 0.02314 = 0.02987 -0.01086 -0.00778 0.00510 C17 1 1.146730 0.265181 0.335222 11.00000 0.02838 0.03089 = 0.02649 -0.00895 -0.01206 0.00360 AFIX 43 H17 2 1.209071 0.227300 0.397195 11.00000 -1.20000 AFIX 0 C16 1 1.028755 0.348914 0.354359 11.00000 0.02535 0.03258 = 0.02612 -0.01526 -0.00629 0.00264 AFIX 43 H16 2 1.009437 0.369755 0.429383 11.00000 -1.20000 AFIX 0 C15 1 0.935537 0.404762 0.265503 11.00000 0.01865 0.02489 = 0.02533 -0.01100 -0.00274 0.00081 C14 1 0.808960 0.493687 0.279147 11.00000 0.02226 0.02867 = 0.02710 -0.01226 -0.00655 0.00191 AFIX 43 H14 2 0.751900 0.523214 0.213152 11.00000 -1.20000 AFIX 0 C13 1 0.761422 0.539981 0.372388 11.00000 0.02010 0.02737 = 0.02886 -0.01270 -0.00603 0.00171 AFIX 43 H13 2 0.817712 0.516176 0.438462 11.00000 -1.20000 AFIX 0 C12 1 0.628383 0.624498 0.377002 11.00000 0.01992 0.02402 = 0.03022 -0.01200 -0.00593 -0.00059 C11 1 0.577977 0.671264 0.473764 11.00000 0.02339 0.02788 = 0.02614 -0.01299 -0.00739 0.00196 AFIX 43 H11 2 0.627693 0.642333 0.544360 11.00000 -1.20000 AFIX 0 C10 1 0.456278 0.759576 0.469861 11.00000 0.02250 0.02464 = 0.02505 -0.01098 -0.00591 -0.00120 C09 1 0.410338 0.820398 0.561890 11.00000 0.02305 0.02607 = 0.02563 -0.01255 -0.00591 0.00074 AFIX 43 H09 2 0.470055 0.803120 0.624742 11.00000 -1.20000 AFIX 0 C08 1 0.287677 0.900283 0.563915 11.00000 0.02278 0.02665 = 0.02466 -0.01160 -0.00514 -0.00020 AFIX 43 H08 2 0.230014 0.914107 0.500386 11.00000 -1.20000 AFIX 0 C05 1 0.231868 0.968113 0.650387 11.00000 0.01978 0.02283 = 0.02246 -0.00896 -0.00297 0.00038 C06 1 0.090727 1.032624 0.649369 11.00000 0.02190 0.03291 = 0.02487 -0.01367 -0.00689 0.00212 AFIX 43 H06 2 0.032763 1.030869 0.590730 11.00000 -1.20000 AFIX 0 C07 1 0.030625 1.099292 0.729723 11.00000 0.01969 0.03038 = 0.02704 -0.01311 -0.00513 0.00381 AFIX 43 H07 2 -0.067236 1.143052 0.726867 11.00000 -1.20000 AFIX 0 C02 1 0.114220 1.101772 0.814408 11.00000 0.02287 0.02571 = 0.02188 -0.01131 -0.00270 0.00156 C01 1 -0.077455 1.230040 0.896922 11.00000 0.02254 0.04678 = 0.04514 -0.02992 -0.00938 0.01198 AFIX 137 H01A 2 -0.073012 1.302759 0.810654 11.00000 -1.50000 H01C 2 -0.099781 1.269528 0.962627 11.00000 -1.50000 H01B 2 -0.160079 1.164005 0.916639 11.00000 -1.50000 AFIX 0 C19 1 1.085747 0.286713 0.138278 11.00000 0.02808 0.03110 = 0.02640 -0.01583 -0.00796 0.00632 AFIX 43 H19 2 1.105180 0.265219 0.063619 11.00000 -1.20000 AFIX 0 C20 1 0.966381 0.370175 0.159548 11.00000 0.02474 0.02918 = 0.02659 -0.01176 -0.01075 0.00614 AFIX 43 H20 2 0.902228 0.405676 0.098793 11.00000 -1.20000 AFIX 0 C03 1 0.256922 1.038829 0.816591 11.00000 0.02260 0.03232 = 0.02804 -0.01470 -0.01099 0.00395 AFIX 43 H03 2 0.315122 1.041475 0.874733 11.00000 -1.20000 AFIX 0 C04 1 0.314445 0.973362 0.736408 11.00000 0.02023 0.02891 = 0.02724 -0.01220 -0.00666 0.00501 AFIX 43 H04 2 0.412752 0.930376 0.739020 11.00000 -1.20000 AFIX 0 B1 4 0.407144 0.725224 0.287903 11.00000 0.02676 0.03290 = 0.03273 -0.01820 -0.01354 0.00661 C22 1 0.497058 0.472680 0.110710 11.00000 0.06526 0.08084 = 0.08026 -0.04597 -0.03955 0.00559 AFIX 23 H22A 2 0.494906 0.506846 0.179180 11.00000 -1.20000 H22B 2 0.459196 0.376707 0.155931 11.00000 -1.20000 AFIX 0 C23 1 0.616272 0.451146 -0.039352 11.00000 0.03725 0.04015 = 0.09309 -0.02246 -0.01895 0.00337 AFIX 23 H23B 2 0.589383 0.353207 -0.007818 11.00000 -1.20000 H23A 2 0.718571 0.466765 -0.102608 11.00000 -1.20000 AFIX 0 O05 3 0.635685 0.470873 0.054937 10.50000 0.03135 0.07003 = 0.04043 -0.02367 -0.00973 0.00098 HKLF 4 1.0 1.00 0.00 0.00 0.00 1.00 0.00 0.00 0.00 1.00 REM purple_a.res in P-1 REM wR2 = 0.1442, GooF = S = 1.023, Restrained GooF = 1.023 for all data REM R1 = 0.0543 for 3272 Fo > 4sig(Fo) and 0.0894 for all 4937 data REM 282 parameters refined using 0 restraints END WGHT 0.0566 0.2083 REM Highest difference peak 0.245, deepest hole -0.289, 1-sigma level 0.055 Q1 1 0.4585 0.8214 0.4965 11.00000 0.05 0.25 Q2 1 0.9191 0.3470 0.2474 11.00000 0.05 0.24 Q3 1 0.7198 0.5052 -0.0331 11.00000 0.05 0.24 Q4 1 0.2315 0.8955 0.6353 11.00000 0.05 0.24 Q5 1 -0.1041 1.2165 0.9937 11.00000 0.05 0.23 Q6 1 0.0824 1.0813 0.6796 11.00000 0.05 0.23 Q7 1 0.6353 0.6974 0.3985 11.00000 0.05 0.22 Q8 1 0.5705 0.5421 0.0932 11.00000 0.05 0.22 Q9 1 0.2761 0.9788 0.6811 11.00000 0.05 0.22 Q10 1 0.0794 1.1003 0.7691 11.00000 0.05 0.21 Q11 1 0.7007 0.5848 0.3713 11.00000 0.05 0.21 Q12 1 0.4812 0.4541 0.1421 11.00000 0.05 0.21 Q13 1 1.1577 0.2978 0.1662 11.00000 0.05 0.20 Q14 1 0.7626 0.4678 0.3561 11.00000 0.05 0.20 Q15 1 1.1868 0.2976 0.2544 11.00000 0.05 0.19 Q16 1 0.3939 0.7480 0.5471 11.00000 0.05 0.19 Q17 1 0.5715 0.6123 0.4511 11.00000 0.05 0.19 Q18 1 1.1373 0.2438 0.2894 11.00000 0.05 0.19 Q19 1 0.6382 0.5422 0.1149 11.00000 0.05 0.18 Q20 1 0.5062 0.6002 0.3573 11.00000 0.05 0.18 ; _shelx_res_checksum 41798 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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.29074(13) 0.63167(11) 0.32627(11) 0.0343(3) Uani 1 1 d . . . . . F2 F 0.40825(13) 0.82068(11) 0.16698(10) 0.0341(3) Uani 1 1 d . . . . . O04 O 1.29900(16) 0.15252(14) 0.21594(13) 0.0354(3) Uani 1 1 d . . . . . O01 O 0.06781(15) 1.16331(14) 0.89815(12) 0.0305(3) Uani 1 1 d . . . . . O03 O 0.55698(15) 0.65695(14) 0.28337(13) 0.0307(3) Uani 1 1 d . . . . . O02 O 0.37979(15) 0.79209(14) 0.37969(12) 0.0301(3) Uani 1 1 d . . . . . C21 C 1.3391(3) 0.1269(2) 0.1007(2) 0.0392(5) Uani 1 1 d . . . . . H21A H 1.251848 0.079714 0.095954 0.059 Uiso 1 1 calc R U . . . H21C H 1.431655 0.069581 0.101752 0.059 Uiso 1 1 calc R U . . . H21B H 1.361432 0.213586 0.024648 0.059 Uiso 1 1 calc R U . . . C18 C 1.1773(2) 0.23437(18) 0.22708(18) 0.0253(4) Uani 1 1 d . . . . . C17 C 1.1467(2) 0.26518(19) 0.33522(18) 0.0285(4) Uani 1 1 d . . . . . H17 H 1.209071 0.227300 0.397195 0.034 Uiso 1 1 calc R U . . . C16 C 1.0288(2) 0.34891(19) 0.35436(17) 0.0269(4) Uani 1 1 d . . . . . H16 H 1.009437 0.369755 0.429383 0.032 Uiso 1 1 calc R U . . . C15 C 0.9355(2) 0.40476(18) 0.26550(17) 0.0231(4) Uani 1 1 d . . . . . C14 C 0.8090(2) 0.49369(18) 0.27915(17) 0.0255(4) Uani 1 1 d . . . . . H14 H 0.751900 0.523214 0.213152 0.031 Uiso 1 1 calc R U . . . C13 C 0.7614(2) 0.53998(18) 0.37239(17) 0.0249(4) Uani 1 1 d . . . . . H13 H 0.817712 0.516176 0.438462 0.030 Uiso 1 1 calc R U . . . C12 C 0.6284(2) 0.62450(18) 0.37700(17) 0.0242(4) Uani 1 1 d . . . . . C11 C 0.5780(2) 0.67126(18) 0.47376(17) 0.0248(4) Uani 1 1 d . . . . . H11 H 0.627693 0.642333 0.544360 0.030 Uiso 1 1 calc R U . . . C10 C 0.4563(2) 0.75958(18) 0.46986(17) 0.0235(4) Uani 1 1 d . . . . . C09 C 0.4103(2) 0.82040(18) 0.56189(17) 0.0241(4) Uani 1 1 d . . . . . H09 H 0.470055 0.803120 0.624742 0.029 Uiso 1 1 calc R U . . . C08 C 0.2877(2) 0.90028(18) 0.56391(17) 0.0242(4) Uani 1 1 d . . . . . H08 H 0.230014 0.914107 0.500386 0.029 Uiso 1 1 calc R U . . . C05 C 0.2319(2) 0.96811(17) 0.65039(16) 0.0221(4) Uani 1 1 d . . . . . C06 C 0.0907(2) 1.03262(19) 0.64937(17) 0.0256(4) Uani 1 1 d . . . . . H06 H 0.032763 1.030869 0.590730 0.031 Uiso 1 1 calc R U . . . C07 C 0.0306(2) 1.09929(19) 0.72972(17) 0.0254(4) Uani 1 1 d . . . . . H07 H -0.067236 1.143052 0.726867 0.030 Uiso 1 1 calc R U . . . C02 C 0.1142(2) 1.10177(18) 0.81441(16) 0.0234(4) Uani 1 1 d . . . . . C01 C -0.0775(2) 1.2300(2) 0.8969(2) 0.0347(5) Uani 1 1 d . . . . . H01A H -0.073012 1.302759 0.810654 0.052 Uiso 1 1 calc R U . . . H01C H -0.099781 1.269528 0.962627 0.052 Uiso 1 1 calc R U . . . H01B H -0.160079 1.164005 0.916639 0.052 Uiso 1 1 calc R U . . . C19 C 1.0857(2) 0.28671(19) 0.13828(18) 0.0271(4) Uani 1 1 d . . . . . H19 H 1.105180 0.265219 0.063619 0.033 Uiso 1 1 calc R U . . . C20 C 0.9664(2) 0.37018(18) 0.15955(17) 0.0260(4) Uani 1 1 d . . . . . H20 H 0.902228 0.405676 0.098793 0.031 Uiso 1 1 calc R U . . . C03 C 0.2569(2) 1.03883(19) 0.81659(17) 0.0260(4) Uani 1 1 d . . . . . H03 H 0.315122 1.041475 0.874733 0.031 Uiso 1 1 calc R U . . . C04 C 0.3144(2) 0.97336(18) 0.73641(17) 0.0252(4) Uani 1 1 d . . . . . H04 H 0.412752 0.930376 0.739020 0.030 Uiso 1 1 calc R U . . . B1 B 0.4071(3) 0.7252(2) 0.2879(2) 0.0282(5) Uani 1 1 d . . . . . C22 C 0.4971(3) 0.4727(3) 0.1107(3) 0.0668(8) Uani 1 1 d . . . . . H22A H 0.494906 0.506846 0.179180 0.080 Uiso 1 1 calc R U . . . H22B H 0.459196 0.376707 0.155931 0.080 Uiso 1 1 calc R U . . . C23 C 0.6163(3) 0.4511(3) -0.0394(3) 0.0575(7) Uani 1 1 d . . . . . H23B H 0.589383 0.353207 -0.007818 0.069 Uiso 1 1 calc R U . . . H23A H 0.718571 0.466765 -0.102608 0.069 Uiso 1 1 calc R U . . . O05 O 0.6357(4) 0.4709(4) 0.0549(3) 0.0464(8) Uani 0.5 1 d . . P . . 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 0.0310(6) 0.0381(6) 0.0385(6) -0.0177(5) -0.0111(5) -0.0007(5) F2 0.0357(7) 0.0357(6) 0.0321(6) -0.0138(5) -0.0117(5) 0.0072(5) O04 0.0345(8) 0.0379(8) 0.0427(8) -0.0233(7) -0.0178(6) 0.0191(6) O01 0.0246(7) 0.0419(8) 0.0359(7) -0.0263(6) -0.0109(6) 0.0111(6) O03 0.0281(7) 0.0397(8) 0.0359(7) -0.0244(6) -0.0152(6) 0.0120(6) O02 0.0266(7) 0.0378(8) 0.0366(7) -0.0232(6) -0.0143(6) 0.0108(6) C21 0.0375(12) 0.0447(12) 0.0502(13) -0.0334(11) -0.0173(10) 0.0198(10) C18 0.0234(9) 0.0231(9) 0.0299(9) -0.0109(8) -0.0078(7) 0.0051(7) C17 0.0284(10) 0.0309(10) 0.0265(9) -0.0089(8) -0.0121(8) 0.0036(8) C16 0.0253(9) 0.0326(10) 0.0261(9) -0.0153(8) -0.0063(8) 0.0026(8) C15 0.0187(8) 0.0249(9) 0.0253(9) -0.0110(7) -0.0027(7) 0.0008(7) C14 0.0223(9) 0.0287(9) 0.0271(9) -0.0123(8) -0.0065(7) 0.0019(8) C13 0.0201(8) 0.0274(9) 0.0289(9) -0.0127(8) -0.0060(7) 0.0017(8) C12 0.0199(8) 0.0240(9) 0.0302(9) -0.0120(8) -0.0059(7) -0.0006(7) C11 0.0234(9) 0.0279(9) 0.0261(9) -0.0130(8) -0.0074(7) 0.0020(8) C10 0.0225(9) 0.0246(9) 0.0250(9) -0.0110(7) -0.0059(7) -0.0012(7) C09 0.0231(9) 0.0261(9) 0.0256(9) -0.0125(7) -0.0059(7) 0.0007(7) C08 0.0228(9) 0.0266(9) 0.0247(9) -0.0116(8) -0.0051(7) -0.0002(7) C05 0.0198(8) 0.0228(9) 0.0225(9) -0.0090(7) -0.0030(7) 0.0004(7) C06 0.0219(9) 0.0329(10) 0.0249(9) -0.0137(8) -0.0069(7) 0.0021(8) C07 0.0197(8) 0.0304(10) 0.0270(9) -0.0131(8) -0.0051(7) 0.0038(8) C02 0.0229(9) 0.0257(9) 0.0219(9) -0.0113(7) -0.0027(7) 0.0016(7) C01 0.0225(10) 0.0468(12) 0.0451(12) -0.0299(10) -0.0094(9) 0.0120(9) C19 0.0281(10) 0.0311(10) 0.0264(9) -0.0158(8) -0.0080(8) 0.0063(8) C20 0.0247(9) 0.0292(10) 0.0266(9) -0.0118(8) -0.0108(8) 0.0061(8) C03 0.0226(9) 0.0323(10) 0.0280(9) -0.0147(8) -0.0110(8) 0.0040(8) C04 0.0202(8) 0.0289(10) 0.0272(9) -0.0122(8) -0.0067(7) 0.0050(8) B1 0.0268(11) 0.0329(11) 0.0327(11) -0.0182(10) -0.0135(9) 0.0066(9) C22 0.0653(19) 0.081(2) 0.080(2) -0.0460(18) -0.0395(17) 0.0056(17) C23 0.0372(13) 0.0402(14) 0.093(2) -0.0225(14) -0.0190(14) 0.0034(11) O05 0.0313(17) 0.070(2) 0.0404(17) -0.0237(17) -0.0097(14) 0.0010(16) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 '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 C18 O04 C21 116.80(16) . . ? C02 O01 C01 116.77(16) . . ? C12 O03 B1 121.61(18) . . ? C10 O02 B1 121.87(19) . . ? O04 C21 H21A 109.5 . . ? O04 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? O04 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? H21C C21 H21B 109.5 . . ? O04 C18 C17 115.91(17) . . ? O04 C18 C19 124.1(2) . . ? C17 C18 C19 120.0(2) . . ? C16 C17 C18 120.63(17) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C16 C15 120.7(2) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C20 C15 C16 117.6(2) . . ? C20 C15 C14 118.51(17) . . ? C16 C15 C14 123.9(2) . . ? C13 C14 C15 127.93(18) . . ? C13 C14 H14 116.0 . . ? C15 C14 H14 116.0 . . ? C14 C13 C12 122.13(18) . . ? C14 C13 H13 118.9 . . ? C12 C13 H13 118.9 . . ? O03 C12 C11 120.8(2) . . ? O03 C12 C13 116.91(19) . . ? C11 C12 C13 122.31(18) . . ? C12 C11 C10 120.43(18) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? O02 C10 C11 120.57(19) . . ? O02 C10 C09 117.5(2) . . ? C11 C10 C09 121.96(18) . . ? C08 C09 C10 122.78(18) . . ? C08 C09 H09 118.6 . . ? C10 C09 H09 118.6 . . ? C09 C08 C05 127.66(18) . . ? C09 C08 H08 116.2 . . ? C05 C08 H08 116.2 . . ? C06 C05 C04 117.5(2) . . ? C06 C05 C08 119.52(18) . . ? C04 C05 C08 123.0(2) . . ? C07 C06 C05 122.43(18) . . ? C07 C06 H06 118.8 . . ? C05 C06 H06 118.8 . . ? C06 C07 C02 118.8(2) . . ? C06 C07 H07 120.6 . . ? C02 C07 H07 120.6 . . ? O01 C02 C07 124.5(2) . . ? O01 C02 C03 115.59(17) . . ? C07 C02 C03 119.9(2) . . ? O01 C01 H01A 109.5 . . ? O01 C01 H01C 109.5 . . ? H01A C01 H01C 109.5 . . ? O01 C01 H01B 109.5 . . ? H01A C01 H01B 109.5 . . ? H01C C01 H01B 109.5 . . ? C20 C19 C18 118.6(2) . . ? C20 C19 H19 120.7 . . ? C18 C19 H19 120.7 . . ? C19 C20 C15 122.44(17) . . ? C19 C20 H20 118.8 . . ? C15 C20 H20 118.8 . . ? C04 C03 C02 120.41(18) . . ? C04 C03 H03 119.8 . . ? C02 C03 H03 119.8 . . ? C03 C04 C05 121.0(2) . . ? C03 C04 H04 119.5 . . ? C05 C04 H04 119.5 . . ? F2 B1 F1 110.36(19) . . ? F2 B1 O03 108.13(19) . . ? F1 B1 O03 109.3(2) . . ? F2 B1 O02 109.0(3) . . ? F1 B1 O02 108.6(2) . . ? O03 B1 O02 111.46(16) . . ? O05 C22 C23 121.2(3) . 2_665 ? O05 C22 C23 40.67(18) . . ? C23 C22 C23 90.1(3) 2_665 . ? O05 C22 H22A 107.0 . . ? C23 C22 H22A 107.0 2_665 . ? C23 C22 H22A 146.4 . . ? O05 C22 H22B 107.0 . . ? C23 C22 H22B 107.0 2_665 . ? C23 C22 H22B 94.9 . . ? H22A C22 H22B 106.8 . . ? O05 C23 C22 120.9(3) . 2_665 ? O05 C23 C22 40.6(2) . . ? C22 C23 C22 89.9(3) 2_665 . ? O05 C23 H23B 107.1 . . ? C22 C23 H23B 107.1 2_665 . ? C22 C23 H23B 95.0 . . ? O05 C23 H23A 107.1 . . ? C22 C23 H23A 107.1 2_665 . ? C22 C23 H23A 146.3 . . ? H23B C23 H23A 106.8 . . ? C22 O05 C23 98.7(3) . . ? 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 B1 1.360(4) . ? F2 B1 1.356(4) . ? O04 C18 1.344(3) . ? O04 C21 1.418(4) . ? O01 C02 1.343(3) . ? O01 C01 1.416(4) . ? O03 C12 1.297(3) . ? O03 B1 1.458(4) . ? O02 C10 1.294(3) . ? O02 B1 1.464(3) . ? C21 H21A 0.9800 . ? C21 H21C 0.9800 . ? C21 H21B 0.9800 . ? C18 C17 1.373(4) . ? C18 C19 1.374(3) . ? C17 C16 1.352(3) . ? C17 H17 0.9500 . ? C16 C15 1.388(3) . ? C16 H16 0.9500 . ? C15 C20 1.373(4) . ? C15 C14 1.427(3) . ? C14 C13 1.322(3) . ? C14 H14 0.9500 . ? C13 C12 1.426(3) . ? C13 H13 0.9500 . ? C12 C11 1.363(3) . ? C11 C10 1.368(3) . ? C11 H11 0.9500 . ? C10 C09 1.418(3) . ? C09 C08 1.325(3) . ? C09 H09 0.9500 . ? C08 C05 1.429(3) . ? C08 H08 0.9500 . ? C05 C06 1.375(4) . ? C05 C04 1.389(3) . ? C06 C07 1.369(3) . ? C06 H06 0.9500 . ? C07 C02 1.371(3) . ? C07 H07 0.9500 . ? C02 C03 1.380(4) . ? C01 H01A 0.9800 . ? C01 H01C 0.9800 . ? C01 H01B 0.9800 . ? C19 C20 1.364(3) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? C03 C04 1.354(3) . ? C03 H03 0.9500 . ? C04 H04 0.9500 . ? C22 O05 1.238(5) . ? C22 C23 1.441(4) 2_665 ? C22 C23 1.881(5) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O05 1.240(5) . ? C23 H23B 0.9900 . ? C23 H23A 0.9900 . ? 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 _geom_hbond_publ_flag C21 H21C F2 0.98 2.47 3.094(8) 121.1 1_645 yes C13 H13 F1 0.95 2.51 3.144(8) 124.1 2_666 yes C01 H01B F2 0.98 2.57 3.323(7) 133.2 2_576 yes C21 H21C F2 0.98 2.47 3.094(8) 121.1 1_645 yes C13 H13 F1 0.95 2.51 3.144(8) 124.1 2_666 yes C01 H01B F2 0.98 2.57 3.323(7) 133.2 2_576 yes 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 C21 O04 C18 C17 -175.88(17) . . . . ? C21 O04 C18 C19 4.0(3) . . . . ? O04 C18 C17 C16 178.68(17) . . . . ? C19 C18 C17 C16 -1.2(3) . . . . ? C18 C17 C16 C15 0.4(3) . . . . ? C17 C16 C15 C20 0.9(3) . . . . ? C17 C16 C15 C14 179.92(18) . . . . ? C20 C15 C14 C13 -179.28(18) . . . . ? C16 C15 C14 C13 1.7(3) . . . . ? C15 C14 C13 C12 -177.41(18) . . . . ? B1 O03 C12 C11 -10.1(3) . . . . ? B1 O03 C12 C13 170.67(17) . . . . ? C14 C13 C12 O03 -1.5(3) . . . . ? C14 C13 C12 C11 179.28(17) . . . . ? O03 C12 C11 C10 -3.7(3) . . . . ? C13 C12 C11 C10 175.56(17) . . . . ? B1 O02 C10 C11 7.1(3) . . . . ? B1 O02 C10 C09 -173.80(16) . . . . ? C12 C11 C10 O02 5.2(3) . . . . ? C12 C11 C10 C09 -173.88(17) . . . . ? O02 C10 C09 C08 4.7(3) . . . . ? C11 C10 C09 C08 -176.25(18) . . . . ? C10 C09 C08 C05 -179.13(17) . . . . ? C09 C08 C05 C06 -171.47(19) . . . . ? C09 C08 C05 C04 9.0(3) . . . . ? C04 C05 C06 C07 -0.5(3) . . . . ? C08 C05 C06 C07 179.95(16) . . . . ? C05 C06 C07 C02 0.0(3) . . . . ? C01 O01 C02 C07 -0.3(3) . . . . ? C01 O01 C02 C03 179.31(17) . . . . ? C06 C07 C02 O01 -179.84(16) . . . . ? C06 C07 C02 C03 0.6(3) . . . . ? O04 C18 C19 C20 -179.21(18) . . . . ? C17 C18 C19 C20 0.7(3) . . . . ? C18 C19 C20 C15 0.7(3) . . . . ? C16 C15 C20 C19 -1.5(3) . . . . ? C14 C15 C20 C19 179.47(17) . . . . ? O01 C02 C03 C04 179.77(16) . . . . ? C07 C02 C03 C04 -0.6(3) . . . . ? C02 C03 C04 C05 0.1(3) . . . . ? C06 C05 C04 C03 0.5(3) . . . . ? C08 C05 C04 C03 -179.99(17) . . . . ? C12 O03 B1 F2 140.0(2) . . . . ? C12 O03 B1 F1 -99.9(2) . . . . ? C12 O03 B1 O02 20.1(3) . . . . ? C10 O02 B1 F2 -137.97(19) . . . . ? C10 O02 B1 F1 101.7(3) . . . . ? C10 O02 B1 O03 -18.7(3) . . . . ? C23 C22 C23 O05 142.3(4) 2_665 . . . ? O05 C22 C23 C22 -142.3(4) . . . 2_665 ? C23 C22 C23 C22 0.002(2) 2_665 . . 2_665 ? C23 C22 O05 C23 -45.6(5) 2_665 . . . ? C22 C23 O05 C22 45.4(5) 2_665 . . . ?