#------------------------------------------------------------------------------ #$Date: 2015-12-02 06:06:55 +0200 (Wed, 02 Dec 2015) $ #$Revision: 170641 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/54/05/1540582.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_1540582 loop_ _publ_author_name 'Boerth, Jeffrey A.' 'Ellman, Jonathan A.' _publ_section_title ; Rh(iii)-catalyzed diastereoselective C--H bond addition/cyclization cascade of enone tethered aldehydes ; _journal_name_full 'Chem. Sci.' _journal_paper_doi 10.1039/C5SC04138D _journal_year 2016 _chemical_formula_moiety '2(C25 H22 F3 N O2), 0.5(C7 H8)' _chemical_formula_sum 'C53.5 H48 F6 N2 O4' _chemical_formula_weight 896.94 _chemical_name_systematic (2-hydroxy-6-(2-(pyridin-2-yl)phenyl)cyclohexyl)(4-(trifluoromethyl)phenyl)methanone _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 mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2015-07-20 deposited with the CCDC. 2015-11-23 downloaded from the CCDC. ; _cell_angle_alpha 96.651(7) _cell_angle_beta 91.573(7) _cell_angle_gamma 109.521(8) _cell_formula_units_Z 2 _cell_length_a 9.6325(2) _cell_length_b 13.4130(3) _cell_length_c 18.8693(13) _cell_measurement_reflns_used 22475 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 66.6 _cell_measurement_theta_min 2.4 _cell_volume 2276.6(2) _computing_cell_refinement 'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)' _computing_data_collection 'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)' _computing_data_reduction 'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)' _computing_molecular_graphics ; Dolomanov, O.V.; Bourhis, L.J.; Gildea, R.J.; Howard, J.A.K.; Puschmann, H., OLEX2: A complete structure solution, refinement and analysis program (2009). J. Appl. Cryst., 42, 339-341. ; _computing_publication_material 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 93(2) _diffrn_detector_area_resol_mean 22.2 _diffrn_measured_fraction_theta_full 0.983 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Rigaku Saturn 944+ CCD' _diffrn_measurement_method \w _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54187 _diffrn_reflns_av_R_equivalents 0.0480 _diffrn_reflns_av_unetI/netI 0.0261 _diffrn_reflns_laue_measured_fraction_full 0.983 _diffrn_reflns_laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 59268 _diffrn_reflns_point_group_measured_fraction_full 0.983 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 66.591 _diffrn_reflns_theta_max 66.591 _diffrn_reflns_theta_min 2.363 _diffrn_source 'Rotating Anode' _exptl_absorpt_coefficient_mu 0.825 _exptl_absorpt_correction_T_max 0.968 _exptl_absorpt_correction_T_min 0.802 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Jacobson, R. (1998) Private Communication' _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 938 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Toluene, Hexane' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.040 _refine_diff_density_max 0.529 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.038 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 659 _refine_ls_number_reflns 7910 _refine_ls_number_restraints 51 _refine_ls_restrained_S_all 1.115 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0394 _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^)+(0.0463P)^2^+0.8691P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1018 _refine_ls_wR_factor_ref 0.1039 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7081 _reflns_number_total 7910 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c5sc04138d2.cif _cod_data_source_block 007-15013 _cod_original_formula_sum 'C53.50 H48 F6 N2 O4' _cod_database_code 1540582 _audit_block_doi 10.5517/cc1jgcp1 _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_min 0.852 _shelx_estimated_absorpt_t_max 0.968 _shelx_res_file ; 007-15013.res created by SHELXL-2014/7 TITL JAB1-412 CELL 1.54187 9.6325 13.413 18.8693 96.651 91.573 109.521 ZERR 2 0.0002 0.0003 0.0013 0.007 0.007 0.008 LATT 1 SFAC C H F N O UNIT 107 96 12 4 8 DFIX 1.396 0.002 C54 C53 C55 C54 C56 C55 C57 C56 C57 C52 C53 C52 RIGU F4A > F6B RIGU C51 C52 C53 C55 C56 C57 C54 L.S. 10 TEMP -180 SIZE 0.20 0.20 0.04 BOND $H MORE -1 CONF ACTA EQIV $1 x, y+1, z HTAB O1 N2_$1 HTAB O3 N1 WGHT 0.046300 0.869100 FVAR 0.45218 0.51021 F1 3 0.326158 1.002106 0.952606 11.00000 0.09552 0.02739 = 0.05771 -0.00035 0.03491 0.00903 F2 3 0.116673 0.928468 0.993791 11.00000 0.05754 0.05090 = 0.04971 -0.00809 0.00934 0.02962 F3 3 0.312649 0.920785 1.044206 11.00000 0.07819 0.06361 = 0.03301 -0.01607 -0.00921 0.03649 O1 5 0.363294 0.587005 0.663059 11.00000 0.03431 0.02756 = 0.02796 0.00832 0.00156 0.00646 H1 2 0.424669 0.635201 0.639473 11.00000 0.06614 O2 5 0.073568 0.491820 0.751247 11.00000 0.02787 0.03147 = 0.03717 -0.00151 -0.00167 0.00781 N1 4 0.090791 0.150274 0.612535 11.00000 0.07137 0.08496 = 0.02489 -0.01171 -0.01101 0.05962 C1 1 0.438844 0.583644 0.728026 11.00000 0.02783 0.02150 = 0.02614 0.00334 0.00140 0.00658 AFIX 13 H1A 2 0.472252 0.655984 0.756829 11.00000 -1.20000 AFIX 0 C2 1 0.325684 0.503783 0.769096 11.00000 0.02646 0.02098 = 0.02278 0.00296 0.00167 0.00673 AFIX 13 H2 2 0.375053 0.503833 0.816423 11.00000 -1.20000 AFIX 0 C3 1 0.278428 0.389417 0.729021 11.00000 0.02830 0.01998 = 0.02291 0.00323 0.00193 0.00557 AFIX 13 H3A 2 0.229824 0.388978 0.681415 11.00000 -1.20000 AFIX 0 C4 1 0.415504 0.357610 0.716169 11.00000 0.03580 0.02216 = 0.03048 0.00358 0.00631 0.01106 AFIX 23 H4A 2 0.462903 0.354982 0.762810 11.00000 -1.20000 H4B 2 0.384793 0.285261 0.688767 11.00000 -1.20000 AFIX 0 C5 1 0.527306 0.435388 0.675343 11.00000 0.03463 0.02682 = 0.03746 0.00459 0.01157 0.01129 AFIX 23 H5A 2 0.483622 0.433228 0.626840 11.00000 -1.20000 H5B 2 0.615748 0.413915 0.670223 11.00000 -1.20000 AFIX 0 C6 1 0.572270 0.548663 0.714735 11.00000 0.02903 0.02563 = 0.03719 0.00607 0.00727 0.00726 AFIX 23 H6A 2 0.625421 0.552173 0.761119 11.00000 -1.20000 H6B 2 0.640607 0.598456 0.686122 11.00000 -1.20000 AFIX 0 C7 1 0.170432 0.306949 0.767952 11.00000 0.02843 0.02118 = 0.02429 0.00327 0.00312 0.00945 C8 1 0.189257 0.309740 0.841770 11.00000 0.03728 0.02404 = 0.02512 0.00074 0.00165 0.00379 AFIX 43 H8 2 0.267084 0.366761 0.868124 11.00000 -1.20000 AFIX 0 C9 1 0.097631 0.231699 0.877627 11.00000 0.04395 0.03112 = 0.02345 0.00368 0.00673 0.00843 AFIX 43 H9 2 0.112373 0.235898 0.928024 11.00000 -1.20000 AFIX 0 C10 1 -0.015432 0.147561 0.840147 11.00000 0.03603 0.02635 = 0.03072 0.00612 0.01121 0.00721 AFIX 43 H10 2 -0.078246 0.093522 0.864526 11.00000 -1.20000 AFIX 0 C11 1 -0.036296 0.142749 0.766839 11.00000 0.02473 0.02281 = 0.03137 0.00058 0.00374 0.00611 AFIX 43 H11 2 -0.113956 0.084993 0.741008 11.00000 -1.20000 AFIX 0 C12 1 0.055063 0.221489 0.730283 11.00000 0.02394 0.02247 = 0.02490 0.00191 0.00317 0.01056 C13 1 0.027648 0.210510 0.651046 11.00000 0.02295 0.02356 = 0.02682 0.00198 -0.00006 0.00620 C14 1 -0.062608 0.256205 0.619415 11.00000 0.03970 0.04688 = 0.03461 0.01172 0.00436 0.02426 AFIX 43 H14 2 -0.106499 0.299008 0.648012 11.00000 -1.20000 AFIX 0 C15 1 -0.088917 0.239439 0.545908 11.00000 0.03830 0.05936 = 0.03882 0.01787 -0.00373 0.02110 AFIX 43 H15 2 -0.152022 0.269582 0.523439 11.00000 -1.20000 AFIX 0 C16 1 -0.023106 0.179210 0.506380 11.00000 0.06430 0.09018 = 0.02589 -0.00061 -0.01061 0.04230 AFIX 43 H16 2 -0.037910 0.167020 0.455693 11.00000 -1.20000 AFIX 0 C17 1 0.065158 0.136480 0.541433 11.00000 0.10934 0.13821 = 0.02673 -0.01948 -0.01563 0.09776 AFIX 43 H17 2 0.111103 0.094392 0.513540 11.00000 -1.20000 AFIX 0 C18 1 0.193254 0.538816 0.783286 11.00000 0.02764 0.02284 = 0.02434 0.00646 0.00254 0.00616 C19 1 0.209579 0.634306 0.837901 11.00000 0.02840 0.02231 = 0.02327 0.00744 0.00503 0.00815 C20 1 0.089858 0.670776 0.843931 11.00000 0.02706 0.02679 = 0.02809 0.00649 0.00400 0.00753 AFIX 43 H20 2 0.001083 0.633948 0.815021 11.00000 -1.20000 AFIX 0 C21 1 0.098837 0.759727 0.891395 11.00000 0.03438 0.03107 = 0.02813 0.00766 0.00865 0.01488 AFIX 43 H21 2 0.016286 0.783198 0.895525 11.00000 -1.20000 AFIX 0 C22 1 0.228991 0.814469 0.932925 11.00000 0.03914 0.02727 = 0.02112 0.00559 0.00739 0.01252 C23 1 0.348462 0.778635 0.928539 11.00000 0.03398 0.02852 = 0.02187 0.00352 0.00113 0.00838 AFIX 43 H23 2 0.436949 0.815729 0.957602 11.00000 -1.20000 AFIX 0 C24 1 0.338168 0.688543 0.881604 11.00000 0.03015 0.02631 = 0.02451 0.00537 0.00252 0.01102 AFIX 43 H24 2 0.419466 0.663492 0.879176 11.00000 -1.20000 AFIX 0 C25 1 0.244943 0.915352 0.980723 11.00000 0.04651 0.03539 = 0.02844 0.00315 0.00857 0.01591 PART 1 F4A 3 0.658922 0.497123 1.021922 21.00000 0.09211 0.03048 = 0.02953 -0.00294 0.00213 0.00820 PART 0 PART 2 F4B 3 0.647383 0.501924 1.017971 -21.00000 0.03906 0.05384 = 0.05083 -0.02665 0.00193 0.01223 PART 0 PART 1 F5A 3 0.690170 0.582594 0.932547 21.00000 0.13445 0.02394 = 0.04604 -0.00137 0.01213 0.03221 PART 0 PART 2 F5B 3 0.729958 0.591708 0.933686 -21.00000 0.16751 0.02832 = 0.08118 -0.00295 0.01462 0.00888 PART 0 PART 1 F6A 3 0.871032 0.552919 0.976600 21.00000 0.05271 0.06029 = 0.08703 -0.04298 0.00910 -0.01643 PART 0 PART 2 F6B 3 0.867243 0.532235 0.996539 -21.00000 0.03918 0.10044 = 0.09839 -0.06362 -0.02683 0.02015 PART 0 O3 5 0.306277 0.072969 0.662917 11.00000 0.03112 0.03196 = 0.02338 0.00905 0.00399 0.01490 H3 2 0.230254 0.095133 0.650263 11.00000 0.06160 O4 5 0.640837 0.132598 0.703135 11.00000 0.02851 0.02905 = 0.02775 0.00329 0.00853 0.00644 N2 4 0.522427 -0.253089 0.577678 11.00000 0.03581 0.03061 = 0.02325 0.00422 0.00127 0.00432 C26 1 0.290935 0.053461 0.735247 11.00000 0.02550 0.02302 = 0.02108 0.00405 0.00349 0.00974 AFIX 13 H26 2 0.284393 0.118241 0.765018 11.00000 -1.20000 AFIX 0 C27 1 0.431477 0.032519 0.760411 11.00000 0.02260 0.02143 = 0.01809 0.00296 0.00284 0.00735 AFIX 13 H27 2 0.424914 0.021062 0.811820 11.00000 -1.20000 AFIX 0 C28 1 0.441177 -0.068953 0.716798 11.00000 0.02261 0.02245 = 0.01723 0.00213 0.00114 0.00797 AFIX 13 H28 2 0.444801 -0.057887 0.665282 11.00000 -1.20000 AFIX 0 C29 1 0.301862 -0.164141 0.724359 11.00000 0.02415 0.02149 = 0.02405 0.00163 0.00054 0.00809 AFIX 23 H29A 2 0.307130 -0.228558 0.694761 11.00000 -1.20000 H29B 2 0.298046 -0.177807 0.774839 11.00000 -1.20000 AFIX 0 C30 1 0.161840 -0.144370 0.701358 11.00000 0.02302 0.02392 = 0.02856 0.00145 -0.00167 0.00562 AFIX 23 H30A 2 0.074659 -0.205351 0.709992 11.00000 -1.20000 H30B 2 0.159839 -0.139071 0.649469 11.00000 -1.20000 AFIX 0 C31 1 0.153761 -0.041867 0.742501 11.00000 0.02208 0.02635 = 0.02755 0.00410 0.00268 0.00902 AFIX 23 H31A 2 0.065323 -0.028335 0.724161 11.00000 -1.20000 H31B 2 0.143523 -0.050609 0.793688 11.00000 -1.20000 AFIX 0 C32 1 0.574607 -0.097545 0.737589 11.00000 0.02144 0.01743 = 0.02284 0.00366 0.00156 0.00372 C33 1 0.619512 -0.092046 0.809356 11.00000 0.02479 0.02312 = 0.02334 0.00117 0.00021 0.00646 AFIX 43 H33 2 0.572950 -0.061782 0.845380 11.00000 -1.20000 AFIX 0 C34 1 0.730404 -0.129707 0.829238 11.00000 0.02651 0.02716 = 0.02634 0.00502 -0.00421 0.00552 AFIX 43 H34 2 0.758558 -0.125622 0.878427 11.00000 -1.20000 AFIX 0 C35 1 0.800047 -0.173220 0.777487 11.00000 0.02050 0.02698 = 0.03621 0.00817 -0.00105 0.00733 AFIX 43 H35 2 0.875783 -0.199472 0.790905 11.00000 -1.20000 AFIX 0 C36 1 0.758625 -0.178288 0.705884 11.00000 0.02200 0.02450 = 0.03190 0.00480 0.00589 0.00743 AFIX 43 H36 2 0.807356 -0.207345 0.670281 11.00000 -1.20000 AFIX 0 C37 1 0.646493 -0.141350 0.685409 11.00000 0.02035 0.01948 = 0.02443 0.00430 0.00350 0.00370 C38 1 0.601557 -0.153669 0.607586 11.00000 0.02291 0.02672 = 0.02364 0.00395 0.00731 0.01103 C39 1 0.640653 -0.068001 0.568556 11.00000 0.04584 0.02795 = 0.02635 0.00519 0.00965 0.01355 AFIX 43 H39 2 0.696176 0.001680 0.591156 11.00000 -1.20000 AFIX 0 C40 1 0.597741 -0.085377 0.496336 11.00000 0.05658 0.03794 = 0.02640 0.01204 0.01354 0.02336 AFIX 43 H40 2 0.624314 -0.027950 0.468566 11.00000 -1.20000 AFIX 0 C41 1 0.515862 -0.187204 0.465209 11.00000 0.04348 0.04803 = 0.02202 0.00610 0.00565 0.01820 AFIX 43 H41 2 0.484477 -0.201372 0.415779 11.00000 -1.20000 AFIX 0 C42 1 0.480818 -0.267733 0.507613 11.00000 0.04445 0.03842 = 0.02465 0.00148 0.00070 0.00397 AFIX 43 H42 2 0.423907 -0.337749 0.486115 11.00000 -1.20000 AFIX 0 C43 1 0.566802 0.129092 0.754494 11.00000 0.02320 0.02322 = 0.02341 0.00560 0.00165 0.00981 C44 1 0.608238 0.223513 0.812390 11.00000 0.02439 0.02166 = 0.02522 0.00416 -0.00025 0.00816 C45 1 0.519708 0.231900 0.868393 11.00000 0.02681 0.02384 = 0.02332 0.00386 0.00009 0.00637 AFIX 43 H45 2 0.431847 0.174335 0.872951 11.00000 -1.20000 AFIX 0 C46 1 0.559001 0.323709 0.917512 11.00000 0.03330 0.02916 = 0.02447 0.00228 0.00168 0.01116 AFIX 43 H46 2 0.497115 0.329616 0.954953 11.00000 -1.20000 AFIX 0 C47 1 0.688680 0.406738 0.911828 11.00000 0.03340 0.02612 = 0.03373 -0.00257 -0.00247 0.00841 C48 1 0.780258 0.397972 0.857494 11.00000 0.02892 0.02550 = 0.04684 -0.00092 0.00344 0.00226 AFIX 43 H48 2 0.870524 0.454191 0.854453 11.00000 -1.20000 AFIX 0 C49 1 0.739428 0.307293 0.808050 11.00000 0.02765 0.02664 = 0.03647 0.00274 0.00615 0.00788 AFIX 43 H49 2 0.801435 0.301838 0.770577 11.00000 -1.20000 AFIX 0 C50 1 0.730431 0.507851 0.962732 11.00000 0.04485 0.03368 = 0.04731 -0.00765 0.00499 0.00496 PART -1 C51 1 0.142125 0.431501 0.421905 10.50000 0.19123 0.04153 = 0.20394 0.01398 0.15166 -0.00373 AFIX 137 H51A 2 0.236657 0.441805 0.447655 10.50000 -1.50000 H51B 2 0.160062 0.467875 0.379175 10.50000 -1.50000 H51C 2 0.089822 0.355071 0.407694 10.50000 -1.50000 AFIX 0 C52 1 0.042163 0.480931 0.473725 10.50000 0.07386 0.05858 = 0.09061 0.03366 -0.03186 -0.02291 C53 1 0.107776 0.521569 0.542120 10.50000 0.06230 0.04350 = 0.07672 0.04041 -0.01427 -0.02022 AFIX 43 H53 2 0.206210 0.528574 0.556567 10.50000 -1.20000 AFIX 0 C54 1 0.011709 0.550785 0.586923 10.50000 0.10599 0.06242 = 0.05677 0.03164 0.00152 0.00993 AFIX 43 H54 2 0.039755 0.567889 0.636698 10.50000 -1.20000 AFIX 0 C55 1 -0.123434 0.556444 0.563042 10.50000 0.08253 0.08798 = 0.14106 0.02300 0.05906 0.03898 AFIX 43 H55 2 -0.179791 0.579748 0.597569 10.50000 -1.20000 AFIX 0 C56 1 -0.181992 0.530383 0.492132 10.50000 0.07054 0.06034 = 0.10134 0.01025 0.03652 -0.00550 AFIX 43 H56 2 -0.274826 0.532425 0.475439 10.50000 -1.20000 AFIX 0 C57 1 -0.082191 0.500896 0.449821 10.50000 0.05366 0.04471 = 0.06964 0.03039 -0.00353 -0.03301 AFIX 43 H57 2 -0.101273 0.493743 0.399489 10.50000 -1.20000 PART 0 AFIX 0 HKLF 4 REM JAB1-412 REM R1 = 0.0394 for 7081 Fo > 4sig(Fo) and 0.0428 for all 7910 data REM 659 parameters refined using 51 restraints END WGHT 0.0463 0.8691 REM Highest difference peak 0.529, deepest hole -0.338, 1-sigma level 0.038 Q1 1 0.0000 0.5000 0.5000 10.50000 0.05 0.53 Q2 1 0.0883 0.4326 0.4038 11.00000 0.05 0.44 Q3 1 -0.2684 0.6001 0.5123 11.00000 0.05 0.26 Q4 1 -0.1439 0.5417 0.5361 11.00000 0.05 0.23 Q5 1 0.0514 0.0591 0.5247 11.00000 0.05 0.19 Q6 1 0.5801 0.1747 0.7827 11.00000 0.05 0.18 Q7 1 0.3031 0.4426 0.7485 11.00000 0.05 0.17 Q8 1 -0.1390 0.4537 0.3882 11.00000 0.05 0.17 Q9 1 0.4397 -0.0173 0.7398 11.00000 0.05 0.17 Q10 1 0.1809 0.1450 0.5082 11.00000 0.05 0.17 Q11 1 -0.0144 0.1222 0.5370 11.00000 0.05 0.16 Q12 1 0.3458 0.3774 0.7217 11.00000 0.05 0.15 Q13 1 0.4888 0.0759 0.7600 11.00000 0.05 0.15 Q14 1 0.0882 0.2803 0.7503 11.00000 0.05 0.15 Q15 1 0.4038 0.0202 0.7931 11.00000 0.05 0.15 Q16 1 0.1510 0.1955 0.6061 11.00000 0.05 0.15 Q17 1 0.0279 0.1510 0.6328 11.00000 0.05 0.14 Q18 1 0.5041 0.5617 0.7203 11.00000 0.05 0.14 Q19 1 0.2668 0.5191 0.7809 11.00000 0.05 0.14 Q20 1 0.3606 0.0411 0.7484 11.00000 0.05 0.14 ; _shelx_res_checksum 69884 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 0.32616(15) 1.00211(8) 0.95261(6) 0.0631(3) Uani 1 1 d . . . . . F2 F 0.11667(12) 0.92847(8) 0.99379(6) 0.0510(3) Uani 1 1 d . . . . . F3 F 0.31265(14) 0.92079(9) 1.04421(5) 0.0573(3) Uani 1 1 d . . . . . O1 O 0.36329(12) 0.58701(8) 0.66306(5) 0.0306(2) Uani 1 1 d . . . . . H1 H 0.425(3) 0.6352(19) 0.6395(12) 0.066(7) Uiso 1 1 d . . . . . O2 O 0.07357(11) 0.49182(8) 0.75125(6) 0.0333(2) Uani 1 1 d . . . . . N1 N 0.09079(19) 0.15027(15) 0.61253(7) 0.0539(4) Uani 1 1 d . . . . . C1 C 0.43884(16) 0.58364(11) 0.72803(7) 0.0256(3) Uani 1 1 d . . . . . H1A H 0.4723 0.6560 0.7568 0.031 Uiso 1 1 calc R U . . . C2 C 0.32568(15) 0.50378(10) 0.76910(7) 0.0237(3) Uani 1 1 d . . . . . H2 H 0.3751 0.5038 0.8164 0.028 Uiso 1 1 calc R U . . . C3 C 0.27843(16) 0.38942(10) 0.72902(7) 0.0244(3) Uani 1 1 d . . . . . H3A H 0.2298 0.3890 0.6814 0.029 Uiso 1 1 calc R U . . . C4 C 0.41550(17) 0.35761(11) 0.71617(8) 0.0291(3) Uani 1 1 d . . . . . H4A H 0.4629 0.3550 0.7628 0.035 Uiso 1 1 calc R U . . . H4B H 0.3848 0.2853 0.6888 0.035 Uiso 1 1 calc R U . . . C5 C 0.52731(17) 0.43539(12) 0.67534(8) 0.0325(3) Uani 1 1 d . . . . . H5A H 0.4836 0.4332 0.6268 0.039 Uiso 1 1 calc R U . . . H5B H 0.6157 0.4139 0.6702 0.039 Uiso 1 1 calc R U . . . C6 C 0.57227(17) 0.54866(11) 0.71474(8) 0.0309(3) Uani 1 1 d . . . . . H6A H 0.6254 0.5522 0.7611 0.037 Uiso 1 1 calc R U . . . H6B H 0.6406 0.5985 0.6861 0.037 Uiso 1 1 calc R U . . . C7 C 0.17043(16) 0.30695(11) 0.76795(7) 0.0243(3) Uani 1 1 d . . . . . C8 C 0.18926(17) 0.30974(11) 0.84177(8) 0.0307(3) Uani 1 1 d . . . . . H8 H 0.2671 0.3668 0.8681 0.037 Uiso 1 1 calc R U . . . C9 C 0.09763(18) 0.23170(12) 0.87763(8) 0.0338(3) Uani 1 1 d . . . . . H9 H 0.1124 0.2359 0.9280 0.041 Uiso 1 1 calc R U . . . C10 C -0.01543(17) 0.14756(12) 0.84015(8) 0.0315(3) Uani 1 1 d . . . . . H10 H -0.0782 0.0935 0.8645 0.038 Uiso 1 1 calc R U . . . C11 C -0.03630(16) 0.14275(11) 0.76684(8) 0.0270(3) Uani 1 1 d . . . . . H11 H -0.1140 0.0850 0.7410 0.032 Uiso 1 1 calc R U . . . C12 C 0.05506(15) 0.22149(11) 0.73028(7) 0.0232(3) Uani 1 1 d . . . . . C13 C 0.02765(15) 0.21051(11) 0.65105(7) 0.0250(3) Uani 1 1 d . . . . . C14 C -0.06261(18) 0.25621(14) 0.61942(9) 0.0374(4) Uani 1 1 d . . . . . H14 H -0.1065 0.2990 0.6480 0.045 Uiso 1 1 calc R U . . . C15 C -0.08892(19) 0.23944(15) 0.54591(9) 0.0435(4) Uani 1 1 d . . . . . H15 H -0.1520 0.2696 0.5234 0.052 Uiso 1 1 calc R U . . . C16 C -0.0231(2) 0.17921(19) 0.50638(9) 0.0570(5) Uani 1 1 d . . . . . H16 H -0.0379 0.1670 0.4557 0.068 Uiso 1 1 calc R U . . . C17 C 0.0652(3) 0.1365(2) 0.54143(10) 0.0802(9) Uani 1 1 d . . . . . H17 H 0.1111 0.0944 0.5135 0.096 Uiso 1 1 calc R U . . . C18 C 0.19325(16) 0.53882(11) 0.78329(7) 0.0253(3) Uani 1 1 d . . . . . C19 C 0.20958(16) 0.63431(11) 0.83790(7) 0.0243(3) Uani 1 1 d . . . . . C20 C 0.08986(16) 0.67078(11) 0.84393(8) 0.0274(3) Uani 1 1 d . . . . . H20 H 0.0011 0.6339 0.8150 0.033 Uiso 1 1 calc R U . . . C21 C 0.09884(17) 0.75973(12) 0.89140(8) 0.0298(3) Uani 1 1 d . . . . . H21 H 0.0163 0.7832 0.8955 0.036 Uiso 1 1 calc R U . . . C22 C 0.22899(17) 0.81447(11) 0.93293(7) 0.0286(3) Uani 1 1 d . . . . . C23 C 0.34846(17) 0.77863(11) 0.92854(7) 0.0287(3) Uani 1 1 d . . . . . H23 H 0.4369 0.8157 0.9576 0.034 Uiso 1 1 calc R U . . . C24 C 0.33817(16) 0.68854(11) 0.88160(7) 0.0264(3) Uani 1 1 d . . . . . H24 H 0.4195 0.6635 0.8792 0.032 Uiso 1 1 calc R U . . . C25 C 0.24494(19) 0.91535(13) 0.98072(8) 0.0362(4) Uani 1 1 d . . . . . F4A F 0.6589(12) 0.4971(8) 1.0219(5) 0.055(2) Uani 0.51(4) 1 d . . P A 1 F4B F 0.6474(10) 0.5019(9) 1.0180(6) 0.052(2) Uani 0.49(4) 1 d . . P A 2 F5A F 0.690(2) 0.5826(10) 0.9325(5) 0.067(2) Uani 0.51(4) 1 d . . P A 1 F5B F 0.730(3) 0.5917(13) 0.9337(8) 0.099(5) Uani 0.49(4) 1 d . . P A 2 F6A F 0.8710(13) 0.5529(10) 0.9766(9) 0.080(3) Uani 0.51(4) 1 d . . P A 1 F6B F 0.8672(13) 0.5322(18) 0.9965(13) 0.087(4) Uani 0.49(4) 1 d . . P A 2 O3 O 0.30628(11) 0.07297(8) 0.66292(5) 0.0273(2) Uani 1 1 d . . . . . H3 H 0.230(3) 0.0951(17) 0.6503(11) 0.062(6) Uiso 1 1 d . . . . . O4 O 0.64084(11) 0.13260(8) 0.70313(5) 0.0292(2) Uani 1 1 d . . . . . N2 N 0.52243(14) -0.25309(10) 0.57768(6) 0.0316(3) Uani 1 1 d . . . . . C26 C 0.29094(15) 0.05346(11) 0.73525(7) 0.0227(3) Uani 1 1 d . . . . . H26 H 0.2844 0.1182 0.7650 0.027 Uiso 1 1 calc R U . . . C27 C 0.43148(14) 0.03252(10) 0.76041(7) 0.0207(3) Uani 1 1 d . . . . . H27 H 0.4249 0.0211 0.8118 0.025 Uiso 1 1 calc R U . . . C28 C 0.44118(14) -0.06895(10) 0.71680(7) 0.0207(3) Uani 1 1 d . . . . . H28 H 0.4448 -0.0579 0.6653 0.025 Uiso 1 1 calc R U . . . C29 C 0.30186(15) -0.16414(11) 0.72436(7) 0.0233(3) Uani 1 1 d . . . . . H29A H 0.3071 -0.2286 0.6948 0.028 Uiso 1 1 calc R U . . . H29B H 0.2980 -0.1778 0.7748 0.028 Uiso 1 1 calc R U . . . C30 C 0.16184(15) -0.14437(11) 0.70136(8) 0.0260(3) Uani 1 1 d . . . . . H30A H 0.0747 -0.2054 0.7100 0.031 Uiso 1 1 calc R U . . . H30B H 0.1598 -0.1391 0.6495 0.031 Uiso 1 1 calc R U . . . C31 C 0.15376(15) -0.04187(11) 0.74250(8) 0.0251(3) Uani 1 1 d . . . . . H31A H 0.0653 -0.0283 0.7242 0.030 Uiso 1 1 calc R U . . . H31B H 0.1435 -0.0506 0.7937 0.030 Uiso 1 1 calc R U . . . C32 C 0.57461(14) -0.09754(10) 0.73759(7) 0.0212(3) Uani 1 1 d . . . . . C33 C 0.61951(15) -0.09205(11) 0.80936(7) 0.0244(3) Uani 1 1 d . . . . . H33 H 0.5729 -0.0618 0.8454 0.029 Uiso 1 1 calc R U . . . C34 C 0.73040(16) -0.12971(11) 0.82924(8) 0.0276(3) Uani 1 1 d . . . . . H34 H 0.7586 -0.1256 0.8784 0.033 Uiso 1 1 calc R U . . . C35 C 0.80005(15) -0.17322(11) 0.77749(8) 0.0278(3) Uani 1 1 d . . . . . H35 H 0.8758 -0.1995 0.7909 0.033 Uiso 1 1 calc R U . . . C36 C 0.75862(15) -0.17829(11) 0.70588(8) 0.0261(3) Uani 1 1 d . . . . . H36 H 0.8074 -0.2073 0.6703 0.031 Uiso 1 1 calc R U . . . C37 C 0.64649(15) -0.14135(10) 0.68541(7) 0.0220(3) Uani 1 1 d . . . . . C38 C 0.60156(15) -0.15367(11) 0.60759(7) 0.0236(3) Uani 1 1 d . . . . . C39 C 0.64065(18) -0.06800(12) 0.56856(8) 0.0329(3) Uani 1 1 d . . . . . H39 H 0.6962 0.0017 0.5912 0.039 Uiso 1 1 calc R U . . . C40 C 0.5977(2) -0.08538(13) 0.49634(8) 0.0376(4) Uani 1 1 d . . . . . H40 H 0.6243 -0.0280 0.4686 0.045 Uiso 1 1 calc R U . . . C41 C 0.51586(19) -0.18720(14) 0.46521(8) 0.0370(4) Uani 1 1 d . . . . . H41 H 0.4845 -0.2014 0.4158 0.044 Uiso 1 1 calc R U . . . C42 C 0.48082(19) -0.26773(14) 0.50761(8) 0.0387(4) Uani 1 1 d . . . . . H42 H 0.4239 -0.3377 0.4861 0.046 Uiso 1 1 calc R U . . . C43 C 0.56680(15) 0.12909(11) 0.75449(7) 0.0226(3) Uani 1 1 d . . . . . C44 C 0.60824(15) 0.22351(11) 0.81239(7) 0.0236(3) Uani 1 1 d . . . . . C45 C 0.51971(16) 0.23190(11) 0.86839(7) 0.0252(3) Uani 1 1 d . . . . . H45 H 0.4318 0.1743 0.8730 0.030 Uiso 1 1 calc R U . . . C46 C 0.55900(17) 0.32371(11) 0.91751(8) 0.0289(3) Uani 1 1 d . . . . . H46 H 0.4971 0.3296 0.9550 0.035 Uiso 1 1 calc R U . . . C47 C 0.68868(17) 0.40674(12) 0.91183(8) 0.0322(3) Uani 1 1 d . . . . . C48 C 0.78026(18) 0.39797(12) 0.85749(9) 0.0360(4) Uani 1 1 d . . . . . H48 H 0.8705 0.4542 0.8545 0.043 Uiso 1 1 calc R U . . . C49 C 0.73943(17) 0.30729(12) 0.80805(8) 0.0306(3) Uani 1 1 d . . . . . H49 H 0.8014 0.3018 0.7706 0.037 Uiso 1 1 calc R U . . . C50 C 0.7304(2) 0.50785(14) 0.96273(10) 0.0451(4) Uani 1 1 d . . . . . C51 C 0.1421(12) 0.4315(9) 0.4219(6) 0.154(5) Uani 0.5 1 d . U P B -1 H51A H 0.2367 0.4418 0.4477 0.231 Uiso 0.5 1 calc R U P B -1 H51B H 0.1601 0.4679 0.3792 0.231 Uiso 0.5 1 calc R U P B -1 H51C H 0.0898 0.3551 0.4077 0.231 Uiso 0.5 1 calc R U P B -1 C52 C 0.0422(5) 0.4809(4) 0.4737(3) 0.0846(16) Uani 0.5 1 d D U P B -1 C53 C 0.1078(8) 0.5216(7) 0.5421(3) 0.068(2) Uani 0.5 1 d D U P B -1 H53 H 0.2062 0.5286 0.5566 0.082 Uiso 0.5 1 calc R U P B -1 C54 C 0.0117(5) 0.5508(4) 0.5869(3) 0.0779(14) Uani 0.5 1 d D U P B -1 H54 H 0.0398 0.5679 0.6367 0.093 Uiso 0.5 1 calc R U P B -1 C55 C -0.1234(8) 0.5564(9) 0.5630(4) 0.100(3) Uani 0.5 1 d D U P B -1 H55 H -0.1798 0.5797 0.5976 0.120 Uiso 0.5 1 calc R U P B -1 C56 C -0.1820(6) 0.5304(4) 0.4921(3) 0.0839(15) Uani 0.5 1 d D U P B -1 H56 H -0.2748 0.5324 0.4754 0.101 Uiso 0.5 1 calc R U P B -1 C57 C -0.0822(7) 0.5009(7) 0.4498(4) 0.067(2) Uani 0.5 1 d D U P B -1 H57 H -0.1013 0.4937 0.3995 0.080 Uiso 0.5 1 calc R U P B -1 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 0.0955(9) 0.0274(5) 0.0577(7) -0.0003(5) 0.0349(6) 0.0090(5) F2 0.0575(7) 0.0509(6) 0.0497(6) -0.0081(5) 0.0093(5) 0.0296(5) F3 0.0782(8) 0.0636(7) 0.0330(5) -0.0161(5) -0.0092(5) 0.0365(6) O1 0.0343(6) 0.0276(5) 0.0280(5) 0.0083(4) 0.0016(4) 0.0065(5) O2 0.0279(6) 0.0315(6) 0.0372(6) -0.0015(5) -0.0017(5) 0.0078(5) N1 0.0714(11) 0.0850(12) 0.0249(7) -0.0117(7) -0.0110(7) 0.0596(10) C1 0.0278(7) 0.0215(7) 0.0261(7) 0.0033(5) 0.0014(6) 0.0066(6) C2 0.0265(7) 0.0210(7) 0.0228(7) 0.0030(5) 0.0017(5) 0.0067(6) C3 0.0283(7) 0.0200(7) 0.0229(7) 0.0032(5) 0.0019(5) 0.0056(6) C4 0.0358(8) 0.0222(7) 0.0305(8) 0.0036(6) 0.0063(6) 0.0111(6) C5 0.0346(8) 0.0268(8) 0.0375(8) 0.0046(6) 0.0116(7) 0.0113(7) C6 0.0290(8) 0.0256(7) 0.0372(8) 0.0061(6) 0.0073(6) 0.0073(6) C7 0.0284(7) 0.0212(7) 0.0243(7) 0.0033(5) 0.0031(6) 0.0094(6) C8 0.0373(8) 0.0240(7) 0.0251(7) 0.0007(6) 0.0017(6) 0.0038(6) C9 0.0440(9) 0.0311(8) 0.0234(7) 0.0037(6) 0.0067(6) 0.0084(7) C10 0.0360(8) 0.0264(7) 0.0307(8) 0.0061(6) 0.0112(6) 0.0072(6) C11 0.0247(7) 0.0228(7) 0.0314(8) 0.0006(6) 0.0037(6) 0.0061(6) C12 0.0239(7) 0.0225(7) 0.0249(7) 0.0019(5) 0.0032(5) 0.0106(6) C13 0.0230(7) 0.0236(7) 0.0268(7) 0.0020(6) -0.0001(5) 0.0062(6) C14 0.0397(9) 0.0469(9) 0.0346(8) 0.0117(7) 0.0044(7) 0.0243(8) C15 0.0383(9) 0.0594(11) 0.0388(9) 0.0179(8) -0.0037(7) 0.0211(9) C16 0.0643(13) 0.0902(15) 0.0259(9) -0.0006(9) -0.0106(8) 0.0423(12) C17 0.109(2) 0.138(2) 0.0267(9) -0.0195(12) -0.0156(11) 0.0978(19) C18 0.0276(8) 0.0228(7) 0.0243(7) 0.0065(6) 0.0025(6) 0.0062(6) C19 0.0284(7) 0.0223(7) 0.0233(7) 0.0074(5) 0.0050(5) 0.0082(6) C20 0.0271(8) 0.0268(7) 0.0281(7) 0.0065(6) 0.0040(6) 0.0075(6) C21 0.0344(8) 0.0311(8) 0.0281(7) 0.0077(6) 0.0086(6) 0.0149(7) C22 0.0391(8) 0.0273(7) 0.0211(7) 0.0056(6) 0.0074(6) 0.0125(7) C23 0.0340(8) 0.0285(7) 0.0219(7) 0.0035(6) 0.0011(6) 0.0084(6) C24 0.0302(8) 0.0263(7) 0.0245(7) 0.0054(6) 0.0025(6) 0.0110(6) C25 0.0465(10) 0.0354(8) 0.0284(8) 0.0031(6) 0.0086(7) 0.0159(8) F4A 0.092(6) 0.030(3) 0.030(3) -0.003(2) 0.002(3) 0.008(3) F4B 0.039(3) 0.054(4) 0.051(5) -0.027(3) 0.002(2) 0.012(3) F5A 0.134(7) 0.024(3) 0.046(3) -0.0014(19) 0.012(2) 0.032(4) F5B 0.168(13) 0.028(2) 0.081(5) -0.003(2) 0.015(5) 0.009(5) F6A 0.053(3) 0.060(3) 0.087(5) -0.043(3) 0.009(4) -0.016(3) F6B 0.039(4) 0.100(7) 0.098(7) -0.064(5) -0.027(3) 0.020(4) O3 0.0311(6) 0.0320(5) 0.0234(5) 0.0091(4) 0.0040(4) 0.0149(5) O4 0.0285(5) 0.0290(5) 0.0277(5) 0.0033(4) 0.0085(4) 0.0064(4) N2 0.0358(7) 0.0306(7) 0.0233(6) 0.0042(5) 0.0013(5) 0.0043(6) C26 0.0255(7) 0.0230(7) 0.0211(7) 0.0040(5) 0.0035(5) 0.0097(6) C27 0.0226(7) 0.0214(6) 0.0181(6) 0.0030(5) 0.0028(5) 0.0074(5) C28 0.0226(7) 0.0225(7) 0.0172(6) 0.0021(5) 0.0011(5) 0.0080(6) C29 0.0242(7) 0.0215(7) 0.0241(7) 0.0016(5) 0.0005(5) 0.0081(6) C30 0.0230(7) 0.0239(7) 0.0286(7) 0.0015(6) -0.0017(6) 0.0056(6) C31 0.0221(7) 0.0264(7) 0.0276(7) 0.0041(6) 0.0027(5) 0.0090(6) C32 0.0214(7) 0.0174(6) 0.0228(7) 0.0037(5) 0.0016(5) 0.0037(5) C33 0.0248(7) 0.0231(7) 0.0233(7) 0.0012(5) 0.0002(5) 0.0065(6) C34 0.0265(7) 0.0272(7) 0.0263(7) 0.0050(6) -0.0042(6) 0.0055(6) C35 0.0205(7) 0.0270(7) 0.0362(8) 0.0082(6) -0.0011(6) 0.0073(6) C36 0.0220(7) 0.0245(7) 0.0319(7) 0.0048(6) 0.0059(6) 0.0074(6) C37 0.0203(7) 0.0195(6) 0.0244(7) 0.0043(5) 0.0035(5) 0.0037(5) C38 0.0229(7) 0.0267(7) 0.0236(7) 0.0039(5) 0.0073(5) 0.0110(6) C39 0.0458(9) 0.0280(8) 0.0263(7) 0.0052(6) 0.0096(6) 0.0136(7) C40 0.0566(11) 0.0379(9) 0.0264(8) 0.0120(7) 0.0135(7) 0.0234(8) C41 0.0435(9) 0.0480(10) 0.0220(7) 0.0061(7) 0.0057(6) 0.0182(8) C42 0.0444(10) 0.0384(9) 0.0246(8) 0.0015(6) 0.0007(7) 0.0040(7) C43 0.0232(7) 0.0232(7) 0.0234(7) 0.0056(5) 0.0017(5) 0.0098(6) C44 0.0244(7) 0.0217(7) 0.0252(7) 0.0042(5) -0.0002(5) 0.0082(6) C45 0.0268(7) 0.0238(7) 0.0233(7) 0.0039(5) 0.0001(5) 0.0064(6) C46 0.0333(8) 0.0292(7) 0.0245(7) 0.0023(6) 0.0017(6) 0.0112(6) C47 0.0334(8) 0.0261(8) 0.0337(8) -0.0026(6) -0.0025(6) 0.0084(7) C48 0.0289(8) 0.0255(8) 0.0468(9) -0.0009(7) 0.0034(7) 0.0023(6) C49 0.0277(8) 0.0266(7) 0.0365(8) 0.0027(6) 0.0061(6) 0.0079(6) C50 0.0448(11) 0.0337(9) 0.0473(11) -0.0077(8) 0.0050(8) 0.0050(8) C51 0.191(8) 0.042(4) 0.204(8) 0.014(4) 0.152(7) -0.004(4) C52 0.074(3) 0.059(3) 0.091(4) 0.034(3) -0.032(3) -0.023(2) C53 0.062(4) 0.044(4) 0.077(3) 0.040(3) -0.014(3) -0.020(4) C54 0.106(4) 0.062(3) 0.057(3) 0.032(2) 0.002(3) 0.010(3) C55 0.083(4) 0.088(6) 0.141(5) 0.023(4) 0.059(4) 0.039(4) C56 0.071(3) 0.060(3) 0.101(4) 0.010(3) 0.037(3) -0.005(3) C57 0.054(3) 0.045(4) 0.070(3) 0.030(3) -0.004(2) -0.033(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 O1 H1 108.3(15) C13 N1 C17 117.52(15) O1 C1 C6 111.92(12) O1 C1 C2 106.55(11) C6 C1 C2 110.51(11) O1 C1 H1A 109.3 C6 C1 H1A 109.3 C2 C1 H1A 109.3 C18 C2 C3 111.51(11) C18 C2 C1 110.81(11) C3 C2 C1 111.19(11) C18 C2 H2 107.7 C3 C2 H2 107.7 C1 C2 H2 107.7 C7 C3 C4 109.25(11) C7 C3 C2 113.52(11) C4 C3 C2 109.57(11) C7 C3 H3A 108.1 C4 C3 H3A 108.1 C2 C3 H3A 108.1 C5 C4 C3 112.19(12) C5 C4 H4A 109.2 C3 C4 H4A 109.2 C5 C4 H4B 109.2 C3 C4 H4B 109.2 H4A C4 H4B 107.9 C4 C5 C6 110.49(12) C4 C5 H5A 109.6 C6 C5 H5A 109.6 C4 C5 H5B 109.6 C6 C5 H5B 109.6 H5A C5 H5B 108.1 C1 C6 C5 111.83(12) C1 C6 H6A 109.3 C5 C6 H6A 109.3 C1 C6 H6B 109.3 C5 C6 H6B 109.3 H6A C6 H6B 107.9 C8 C7 C12 117.94(13) C8 C7 C3 120.81(13) C12 C7 C3 121.10(12) C9 C8 C7 121.73(14) C9 C8 H8 119.1 C7 C8 H8 119.1 C10 C9 C8 120.01(14) C10 C9 H9 120.0 C8 C9 H9 120.0 C9 C10 C11 119.42(14) C9 C10 H10 120.3 C11 C10 H10 120.3 C10 C11 C12 120.96(13) C10 C11 H11 119.5 C12 C11 H11 119.5 C11 C12 C7 119.94(13) C11 C12 C13 118.14(12) C7 C12 C13 121.91(12) N1 C13 C14 121.63(14) N1 C13 C12 116.03(12) C14 C13 C12 122.28(13) C13 C14 C15 119.66(15) C13 C14 H14 120.2 C15 C14 H14 120.2 C16 C15 C14 118.86(16) C16 C15 H15 120.6 C14 C15 H15 120.6 C15 C16 C17 118.24(16) C15 C16 H16 120.9 C17 C16 H16 120.9 N1 C17 C16 124.07(18) N1 C17 H17 118.0 C16 C17 H17 118.0 O2 C18 C19 118.82(13) O2 C18 C2 121.45(13) C19 C18 C2 119.73(12) C24 C19 C20 118.65(13) C24 C19 C18 123.44(13) C20 C19 C18 117.90(13) C21 C20 C19 120.92(14) C21 C20 H20 119.5 C19 C20 H20 119.5 C20 C21 C22 119.64(14) C20 C21 H21 120.2 C22 C21 H21 120.2 C21 C22 C23 120.35(13) C21 C22 C25 120.55(14) C23 C22 C25 119.05(14) C24 C23 C22 119.77(14) C24 C23 H23 120.1 C22 C23 H23 120.1 C23 C24 C19 120.64(14) C23 C24 H24 119.7 C19 C24 H24 119.7 F2 C25 F3 106.27(13) F2 C25 F1 106.38(13) F3 C25 F1 105.79(14) F2 C25 C22 113.47(14) F3 C25 C22 112.57(13) F1 C25 C22 111.82(12) C26 O3 H3 106.7(14) C38 N2 C42 117.55(13) O3 C26 C31 111.52(11) O3 C26 C27 106.83(10) C31 C26 C27 110.48(11) O3 C26 H26 109.3 C31 C26 H26 109.3 C27 C26 H26 109.3 C43 C27 C28 111.64(11) C43 C27 C26 109.86(10) C28 C27 C26 110.17(11) C43 C27 H27 108.4 C28 C27 H27 108.4 C26 C27 H27 108.4 C32 C28 C29 108.28(10) C32 C28 C27 114.59(11) C29 C28 C27 109.64(11) C32 C28 H28 108.0 C29 C28 H28 108.0 C27 C28 H28 108.0 C30 C29 C28 111.97(11) C30 C29 H29A 109.2 C28 C29 H29A 109.2 C30 C29 H29B 109.2 C28 C29 H29B 109.2 H29A C29 H29B 107.9 C29 C30 C31 111.03(11) C29 C30 H30A 109.4 C31 C30 H30A 109.4 C29 C30 H30B 109.4 C31 C30 H30B 109.4 H30A C30 H30B 108.0 C26 C31 C30 111.55(11) C26 C31 H31A 109.3 C30 C31 H31A 109.3 C26 C31 H31B 109.3 C30 C31 H31B 109.3 H31A C31 H31B 108.0 C33 C32 C37 118.09(12) C33 C32 C28 120.96(12) C37 C32 C28 120.58(12) C34 C33 C32 121.52(13) C34 C33 H33 119.2 C32 C33 H33 119.2 C35 C34 C33 119.97(13) C35 C34 H34 120.0 C33 C34 H34 120.0 C34 C35 C36 119.53(13) C34 C35 H35 120.2 C36 C35 H35 120.2 C35 C36 C37 120.89(13) C35 C36 H36 119.6 C37 C36 H36 119.6 C36 C37 C32 119.98(12) C36 C37 C38 118.52(12) C32 C37 C38 121.45(12) N2 C38 C39 122.16(13) N2 C38 C37 115.69(12) C39 C38 C37 122.14(13) C40 C39 C38 119.16(14) C40 C39 H39 120.4 C38 C39 H39 120.4 C41 C40 C39 119.08(14) C41 C40 H40 120.5 C39 C40 H40 120.5 C42 C41 C40 118.25(14) C42 C41 H41 120.9 C40 C41 H41 120.9 N2 C42 C41 123.79(15) N2 C42 H42 118.1 C41 C42 H42 118.1 O4 C43 C44 119.32(12) O4 C43 C27 121.11(12) C44 C43 C27 119.56(11) C45 C44 C49 118.93(13) C45 C44 C43 123.08(12) C49 C44 C43 117.97(12) C46 C45 C44 120.45(13) C46 C45 H45 119.8 C44 C45 H45 119.8 C47 C46 C45 119.82(14) C47 C46 H46 120.1 C45 C46 H46 120.1 C46 C47 C48 120.25(14) C46 C47 C50 120.64(15) C48 C47 C50 119.09(14) C49 C48 C47 119.69(14) C49 C48 H48 120.2 C47 C48 H48 120.2 C48 C49 C44 120.80(14) C48 C49 H49 119.6 C44 C49 H49 119.6 F5B C50 F4B 107.1(10) F6A C50 F4A 111.8(7) F6A C50 F5A 103.5(10) F4A C50 F5A 104.1(7) F5B C50 F6B 107.1(10) F4B C50 F6B 101.2(10) F6A C50 C47 113.6(6) F5B C50 C47 114.6(7) F4B C50 C47 113.8(5) F4A C50 C47 113.1(5) F5A C50 C47 109.8(5) F6B C50 C47 112.0(6) C52 C51 H51A 109.5 C52 C51 H51B 109.5 H51A C51 H51B 109.5 C52 C51 H51C 109.5 H51A C51 H51C 109.5 H51B C51 H51C 109.5 C57 C52 C53 121.1(5) C57 C52 C51 124.1(6) C53 C52 C51 113.7(6) C52 C53 C54 111.7(5) C52 C53 H53 124.2 C54 C53 H53 124.2 C53 C54 C55 123.8(6) C53 C54 H54 118.1 C55 C54 H54 118.1 C54 C55 C56 124.8(7) C54 C55 H55 117.6 C56 C55 H55 117.6 C57 C56 C55 108.9(6) C57 C56 H56 125.5 C55 C56 H56 125.5 C52 C57 C56 126.6(6) C52 C57 H57 116.7 C56 C57 H57 116.7 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C25 1.3435(19) F2 C25 1.3305(19) F3 C25 1.3307(19) O1 C1 1.4213(17) O1 H1 0.89(2) O2 C18 1.2164(17) N1 C13 1.329(2) N1 C17 1.338(2) C1 C6 1.526(2) C1 C2 1.5474(19) C1 H1A 1.0000 C2 C18 1.5198(19) C2 C3 1.5420(18) C2 H2 1.0000 C3 C7 1.5187(19) C3 C4 1.534(2) C3 H3A 1.0000 C4 C5 1.524(2) C4 H4A 0.9900 C4 H4B 0.9900 C5 C6 1.526(2) C5 H5A 0.9900 C5 H5B 0.9900 C6 H6A 0.9900 C6 H6B 0.9900 C7 C8 1.394(2) C7 C12 1.404(2) C8 C9 1.383(2) C8 H8 0.9500 C9 C10 1.382(2) C9 H9 0.9500 C10 C11 1.383(2) C10 H10 0.9500 C11 C12 1.395(2) C11 H11 0.9500 C12 C13 1.4927(19) C13 C14 1.378(2) C14 C15 1.382(2) C14 H14 0.9500 C15 C16 1.356(3) C15 H15 0.9500 C16 C17 1.368(3) C16 H16 0.9500 C17 H17 0.9500 C18 C19 1.5093(19) C19 C24 1.395(2) C19 C20 1.398(2) C20 C21 1.383(2) C20 H20 0.9500 C21 C22 1.387(2) C21 H21 0.9500 C22 C23 1.388(2) C22 C25 1.496(2) C23 C24 1.386(2) C23 H23 0.9500 C24 H24 0.9500 F4A C50 1.325(9) F4B C50 1.325(9) F5A C50 1.364(11) F5B C50 1.308(14) F6A C50 1.290(12) F6B C50 1.367(12) O3 C26 1.4216(16) O3 H3 0.91(2) O4 C43 1.2149(16) N2 C38 1.3418(18) N2 C42 1.3436(19) C26 C31 1.5235(19) C26 C27 1.5449(18) C26 H26 1.0000 C27 C43 1.5174(19) C27 C28 1.5389(18) C27 H27 1.0000 C28 C32 1.5131(18) C28 C29 1.5359(19) C28 H28 1.0000 C29 C30 1.5203(18) C29 H29A 0.9900 C29 H29B 0.9900 C30 C31 1.5253(19) C30 H30A 0.9900 C30 H30B 0.9900 C31 H31A 0.9900 C31 H31B 0.9900 C32 C33 1.3963(19) C32 C37 1.4034(19) C33 C34 1.385(2) C33 H33 0.9500 C34 C35 1.382(2) C34 H34 0.9500 C35 C36 1.386(2) C35 H35 0.9500 C36 C37 1.3930(19) C36 H36 0.9500 C37 C38 1.4940(19) C38 C39 1.388(2) C39 C40 1.383(2) C39 H39 0.9500 C40 C41 1.379(2) C40 H40 0.9500 C41 C42 1.376(2) C41 H41 0.9500 C42 H42 0.9500 C43 C44 1.5081(19) C44 C45 1.394(2) C44 C49 1.394(2) C45 C46 1.387(2) C45 H45 0.9500 C46 C47 1.385(2) C46 H46 0.9500 C47 C48 1.391(2) C47 C50 1.495(2) C48 C49 1.379(2) C48 H48 0.9500 C49 H49 0.9500 C51 C52 1.628(10) C51 H51A 0.9800 C51 H51B 0.9800 C51 H51C 0.9800 C52 C57 1.387(2) C52 C53 1.387(2) C53 C54 1.390(2) C53 H53 0.9500 C54 C55 1.395(2) C54 H54 0.9500 C55 C56 1.396(2) C55 H55 0.9500 C56 C57 1.393(2) C56 H56 0.9500 C57 H57 0.9500 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 N2 0.89(2) 2.00(2) 2.8782(16) 168(2) 1_565 O3 H3 N1 0.91(2) 1.90(2) 2.8010(17) 171(2) . 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 O1 C1 C2 C18 -58.86(14) C6 C1 C2 C18 179.34(11) O1 C1 C2 C3 65.76(14) C6 C1 C2 C3 -56.04(15) C18 C2 C3 C7 -57.39(15) C1 C2 C3 C7 178.40(11) C18 C2 C3 C4 -179.83(11) C1 C2 C3 C4 55.96(14) C7 C3 C4 C5 178.42(12) C2 C3 C4 C5 -56.64(15) C3 C4 C5 C6 56.56(17) O1 C1 C6 C5 -62.77(15) C2 C1 C6 C5 55.81(16) C4 C5 C6 C1 -55.88(17) C4 C3 C7 C8 80.81(16) C2 C3 C7 C8 -41.80(18) C4 C3 C7 C12 -94.63(15) C2 C3 C7 C12 142.75(13) C12 C7 C8 C9 -0.3(2) C3 C7 C8 C9 -175.93(14) C7 C8 C9 C10 0.6(2) C8 C9 C10 C11 -0.4(2) C9 C10 C11 C12 0.0(2) C10 C11 C12 C7 0.2(2) C10 C11 C12 C13 179.15(13) C8 C7 C12 C11 -0.1(2) C3 C7 C12 C11 175.52(12) C8 C7 C12 C13 -178.95(13) C3 C7 C12 C13 -3.4(2) C17 N1 C13 C14 0.8(3) C17 N1 C13 C12 178.2(2) C11 C12 C13 N1 -85.15(18) C7 C12 C13 N1 93.76(18) C11 C12 C13 C14 92.24(18) C7 C12 C13 C14 -88.85(18) N1 C13 C14 C15 0.0(3) C12 C13 C14 C15 -177.20(15) C13 C14 C15 C16 -0.9(3) C14 C15 C16 C17 0.9(3) C13 N1 C17 C16 -0.9(4) C15 C16 C17 N1 0.0(4) C3 C2 C18 O2 -16.58(18) C1 C2 C18 O2 107.86(14) C3 C2 C18 C19 163.79(11) C1 C2 C18 C19 -71.77(15) O2 C18 C19 C24 174.67(13) C2 C18 C19 C24 -5.69(19) O2 C18 C19 C20 -6.32(19) C2 C18 C19 C20 173.32(12) C24 C19 C20 C21 1.0(2) C18 C19 C20 C21 -178.10(12) C19 C20 C21 C22 0.9(2) C20 C21 C22 C23 -1.9(2) C20 C21 C22 C25 175.55(13) C21 C22 C23 C24 1.0(2) C25 C22 C23 C24 -176.50(13) C22 C23 C24 C19 0.9(2) C20 C19 C24 C23 -1.9(2) C18 C19 C24 C23 177.13(12) C21 C22 C25 F2 17.6(2) C23 C22 C25 F2 -164.99(13) C21 C22 C25 F3 138.31(15) C23 C22 C25 F3 -44.25(19) C21 C22 C25 F1 -102.76(17) C23 C22 C25 F1 74.68(18) O3 C26 C27 C43 59.84(13) C31 C26 C27 C43 -178.69(11) O3 C26 C27 C28 -63.56(13) C31 C26 C27 C28 57.90(14) C43 C27 C28 C32 58.15(14) C26 C27 C28 C32 -179.49(10) C43 C27 C28 C29 -179.87(10) C26 C27 C28 C29 -57.51(13) C32 C28 C29 C30 -177.50(11) C27 C28 C29 C30 56.82(14) C28 C29 C30 C31 -55.44(15) O3 C26 C31 C30 62.14(14) C27 C26 C31 C30 -56.51(14) C29 C30 C31 C26 55.09(15) C29 C28 C32 C33 -79.12(15) C27 C28 C32 C33 43.60(17) C29 C28 C32 C37 93.85(14) C27 C28 C32 C37 -143.42(12) C37 C32 C33 C34 -0.8(2) C28 C32 C33 C34 172.33(12) C32 C33 C34 C35 0.5(2) C33 C34 C35 C36 0.3(2) C34 C35 C36 C37 -0.8(2) C35 C36 C37 C32 0.5(2) C35 C36 C37 C38 -177.08(12) C33 C32 C37 C36 0.32(19) C28 C32 C37 C36 -172.85(12) C33 C32 C37 C38 177.81(12) C28 C32 C37 C38 4.64(19) C42 N2 C38 C39 -0.2(2) C42 N2 C38 C37 -179.48(13) C36 C37 C38 N2 73.78(16) C32 C37 C38 N2 -103.75(15) C36 C37 C38 C39 -105.49(16) C32 C37 C38 C39 76.99(18) N2 C38 C39 C40 -0.4(2) C37 C38 C39 C40 178.78(14) C38 C39 C40 C41 0.7(2) C39 C40 C41 C42 -0.3(2) C38 N2 C42 C41 0.6(2) C40 C41 C42 N2 -0.4(3) C28 C27 C43 O4 24.90(17) C26 C27 C43 O4 -97.64(14) C28 C27 C43 C44 -156.60(11) C26 C27 C43 C44 80.87(14) O4 C43 C44 C45 171.74(13) C27 C43 C44 C45 -6.79(19) O4 C43 C44 C49 -6.36(19) C27 C43 C44 C49 175.11(12) C49 C44 C45 C46 2.3(2) C43 C44 C45 C46 -175.83(12) C44 C45 C46 C47 -1.4(2) C45 C46 C47 C48 -0.6(2) C45 C46 C47 C50 177.89(15) C46 C47 C48 C49 1.7(2) C50 C47 C48 C49 -176.79(15) C47 C48 C49 C44 -0.9(2) C45 C44 C49 C48 -1.1(2) C43 C44 C49 C48 177.07(13) C46 C47 C50 F6A 147.2(9) C48 C47 C50 F6A -34.2(9) C46 C47 C50 F5B -113.1(15) C48 C47 C50 F5B 65.4(15) C46 C47 C50 F4B 10.6(6) C48 C47 C50 F4B -170.9(6) C46 C47 C50 F4A 18.4(6) C48 C47 C50 F4A -163.1(6) C46 C47 C50 F5A -97.4(9) C48 C47 C50 F5A 81.1(9) C46 C47 C50 F6B 124.6(15) C48 C47 C50 F6B -56.9(15) C57 C52 C53 C54 19.2(13) C51 C52 C53 C54 -172.6(6) C52 C53 C54 C55 -10.7(11) C53 C54 C55 C56 2.3(15) C54 C55 C56 C57 -1.5(13) C53 C52 C57 C56 -21.6(14) C51 C52 C57 C56 171.5(7) C55 C56 C57 C52 11.0(12)