#------------------------------------------------------------------------------ #$Date: 2020-06-05 13:16:36 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252728 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/78/1557874.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_1557874 loop_ _publ_author_name 'Yan, Chenting' 'Takeshita, Masato' 'Nakatsuji, Jun-ya' 'Kurosaki, Akihiro' 'Sato, Kaoko' 'Shang, Rong' 'Nakamoto, Masaaki' 'Yamamoto, Yohsuke' 'Adachi, Yohei' 'Furukawa, Ko' 'Kishi, Ryohei' 'Nakano, Masayoshi' _publ_section_title ; Synthesis and properties of hypervalent electron-rich pentacoordinate nitrogen compounds ; _journal_issue 19 _journal_name_full 'Chemical Science' _journal_page_first 5082 _journal_paper_doi 10.1039/D0SC00002G _journal_volume 11 _journal_year 2020 _chemical_formula_sum 'C28 H25 F6 N O4' _chemical_formula_weight 553.49 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-08-05 deposited with the CCDC. 2020-04-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.0770(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.7241(3) _cell_length_b 12.3047(3) _cell_length_c 18.3432(5) _cell_measurement_reflns_used 6921 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 23.91 _cell_measurement_theta_min 2.42 _cell_volume 2605.40(12) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0222 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 12410 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 24.865 _diffrn_reflns_theta_max 24.865 _diffrn_reflns_theta_min 1.920 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_T_max 0.975 _exptl_absorpt_correction_T_min 0.827 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.411 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1144 _exptl_crystal_size_max 0.620 _exptl_crystal_size_mid 0.314 _exptl_crystal_size_min 0.204 _refine_diff_density_max 0.443 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 413 _refine_ls_number_reflns 4485 _refine_ls_number_restraints 66 _refine_ls_restrained_S_all 1.139 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0385 _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^)+(0.0482P)^2^+1.3487P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0990 _refine_ls_wR_factor_ref 0.1032 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4012 _reflns_number_total 4485 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0sc00002g2.cif _cod_data_source_block 2Me_b _cod_depositor_comments 'Adding full bibliography for 1557869--1557876.cif.' _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 1557874 _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 0.928 _shelx_estimated_absorpt_t_max 0.975 _shelx_res_file ; yan_exp302_1_0m.res created by SHELXL-2014/7 TITL yan_exp302_1_0m in P2(1)/n CELL 0.71073 11.7241 12.3047 18.3432 90.000 100.077 90.000 ZERR 4.00 0.0003 0.0003 0.0005 0.000 0.001 0.000 LATT 1 SYMM -x+1/2, y+1/2, -z+1/2 SFAC C H N O F UNIT 112 100 4 16 24 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -100 SIZE 0.204 0.314 0.620 L.S. 30 FMAP 2 PLAN 20 BOND $H ACTA 52 REM REM C:\frames\guest\20180228_yan_exp302_1\work\yan_exp302_1_0m.hkl REM SIMU 0.005 F1 > F3a RIGU 0.005 F1 > F3a SIMU 0.005 F4 > F6a RIGU 0.005 F4 > F6a WGHT 0.048200 1.348700 FVAR 0.11513 0.47244 0.59447 Part 1 21 F1 5 0.317853 0.454668 0.336105 21.00000 0.11883 0.09308 = 0.01797 0.00565 0.01601 0.04502 F2 5 0.483428 0.426056 0.311124 21.00000 0.04956 0.11272 = 0.04465 0.03311 -0.02545 -0.01943 F3 5 0.354874 0.308017 0.284985 21.00000 0.08666 0.04728 = 0.04242 0.03137 -0.01988 -0.03568 Part 2 -21 F1A 5 0.281412 0.425491 0.325904 -21.00000 0.06856 0.10417 = 0.02608 0.02446 0.02037 0.01199 F2A 5 0.458168 0.459772 0.325419 -21.00000 0.09982 0.09747 = 0.03878 0.02294 -0.03710 -0.05708 F3A 5 0.387248 0.308971 0.287579 -21.00000 0.09497 0.04946 = 0.03170 0.01577 0.01390 0.02401 Part 0 PART 3 31 F4 5 0.149930 0.399953 -0.322191 31.00000 0.14097 0.09143 = 0.02672 -0.01467 0.01994 -0.06529 F5 5 0.125469 0.263850 -0.256801 31.00000 0.05692 0.03503 = 0.04002 -0.02099 -0.00818 0.00305 F6 5 -0.009056 0.376306 -0.283727 31.00000 0.05049 0.10677 = 0.06061 -0.04219 -0.03449 0.01844 Part 0 PART 4 -31 F4A 5 0.079123 0.286261 -0.265156 -31.00000 0.13460 0.08289 = 0.04649 -0.01761 0.00711 -0.06856 F5A 5 0.040566 0.442490 -0.313428 -31.00000 0.06578 0.12042 = 0.03986 -0.02397 -0.03327 0.01985 F6A 5 0.204281 0.378896 -0.310529 -31.00000 0.06297 0.05971 = 0.02101 -0.01984 0.00294 0.00520 Part 0 C23 1 0.368247 0.414325 0.286006 11.00000 0.04292 0.03683 = 0.02271 0.00318 -0.00080 -0.00654 C24 1 0.111018 0.376378 -0.266488 11.00000 0.05842 0.04936 = 0.02640 -0.00904 -0.00453 -0.00090 O1 4 0.482594 0.754688 0.145909 11.00000 0.02230 0.03515 = 0.02247 0.00286 -0.00183 0.00628 O2 4 0.512247 0.660372 0.046188 11.00000 0.02626 0.02800 = 0.03816 -0.00130 0.00719 0.00893 O3 4 0.009484 0.651985 -0.041859 11.00000 0.02366 0.02220 = 0.04084 0.00345 0.00959 -0.00293 O4 4 0.010902 0.756869 -0.141696 11.00000 0.02441 0.03320 = 0.02602 -0.00018 -0.00511 -0.00928 N1 3 0.258846 0.606484 0.001068 11.00000 0.02597 0.01430 = 0.01619 0.00098 0.00341 0.00107 C1 1 0.257863 0.721959 -0.001805 11.00000 0.02220 0.01568 = 0.01548 0.00031 0.00607 0.00061 C2 1 0.351135 0.781681 0.035833 11.00000 0.01958 0.01968 = 0.01597 0.00090 0.00476 0.00198 C3 1 0.348024 0.895208 0.035683 11.00000 0.01879 0.01886 = 0.01813 -0.00152 0.00306 -0.00143 AFIX 43 H3 2 0.409678 0.934287 0.064707 11.00000 -1.20000 AFIX 0 C4 1 0.256999 0.952287 -0.005861 11.00000 0.01966 0.01618 = 0.01783 0.00009 0.00613 0.00006 C5 1 0.166237 0.891577 -0.045436 11.00000 0.01841 0.01895 = 0.01864 0.00244 0.00274 0.00165 AFIX 43 H5 2 0.104506 0.928437 -0.076041 11.00000 -1.20000 AFIX 0 C6 1 0.163371 0.778927 -0.041460 11.00000 0.01971 0.01878 = 0.01702 0.00035 0.00484 0.00018 C7 1 0.253446 1.076746 -0.010301 11.00000 0.02144 0.01518 = 0.02380 0.00068 0.00323 0.00064 C8 1 0.136848 1.118550 0.005346 11.00000 0.02931 0.02048 = 0.03645 -0.00183 0.00810 0.00456 AFIX 137 H8A 2 0.135553 1.198109 0.002861 11.00000 -1.50000 H8AB 2 0.126524 1.095136 0.054842 11.00000 -1.50000 H8AC 2 0.073975 1.089113 -0.031668 11.00000 -1.50000 AFIX 0 C9 1 0.267309 1.111603 -0.088428 11.00000 0.03666 0.02103 = 0.03021 0.00519 0.00897 -0.00023 AFIX 137 H9A 2 0.204611 1.080115 -0.124619 11.00000 -1.50000 H9AB 2 0.342078 1.085953 -0.098625 11.00000 -1.50000 H9AC 2 0.264108 1.191043 -0.092030 11.00000 -1.50000 AFIX 0 C10 1 0.349849 1.128993 0.045504 11.00000 0.03188 0.01794 = 0.03832 -0.00280 -0.00320 -0.00176 AFIX 137 H10A 2 0.425295 1.105636 0.035107 11.00000 -1.50000 H10B 2 0.342299 1.106580 0.095706 11.00000 -1.50000 H10C 2 0.343797 1.208280 0.041500 11.00000 -1.50000 AFIX 0 C11 1 0.281176 0.554708 0.070995 11.00000 0.02136 0.01787 = 0.01698 0.00025 0.00222 -0.00353 C12 1 0.351830 0.463091 0.081751 11.00000 0.02505 0.01944 = 0.01935 -0.00099 0.00456 0.00137 AFIX 43 H12 2 0.381719 0.432489 0.041424 11.00000 -1.20000 AFIX 0 C13 1 0.378327 0.416816 0.151360 11.00000 0.02605 0.02040 = 0.02445 0.00193 0.00109 0.00091 AFIX 43 H13 2 0.426152 0.354059 0.158765 11.00000 -1.20000 AFIX 0 C14 1 0.335194 0.461845 0.210563 11.00000 0.02820 0.02392 = 0.01903 0.00103 0.00028 -0.00811 C15 1 0.263853 0.552363 0.199683 11.00000 0.03461 0.02512 = 0.01812 -0.00352 0.00879 -0.00459 AFIX 43 H15 2 0.233937 0.582833 0.240042 11.00000 -1.20000 AFIX 0 C16 1 0.236284 0.598261 0.129995 11.00000 0.02778 0.01809 = 0.02430 -0.00069 0.00761 0.00161 AFIX 43 H16 2 0.186550 0.659701 0.122403 11.00000 -1.20000 AFIX 0 C17 1 0.227546 0.545902 -0.064701 11.00000 0.02010 0.01718 = 0.01758 -0.00028 0.00197 0.00467 C18 1 0.160115 0.452519 -0.065274 11.00000 0.02434 0.01970 = 0.02009 0.00202 0.00402 0.00184 AFIX 43 H18 2 0.139049 0.426833 -0.020623 11.00000 -1.20000 AFIX 0 C19 1 0.124030 0.397479 -0.130674 11.00000 0.02594 0.02060 = 0.02818 -0.00229 -0.00007 -0.00010 AFIX 43 H19 2 0.078499 0.333577 -0.130883 11.00000 -1.20000 AFIX 0 C20 1 0.153814 0.434852 -0.196261 11.00000 0.03277 0.02740 = 0.02150 -0.00302 -0.00157 0.00601 C21 1 0.221544 0.527499 -0.195831 11.00000 0.04035 0.02773 = 0.01799 0.00211 0.00762 0.00563 AFIX 43 H21 2 0.242075 0.553196 -0.240632 11.00000 -1.20000 AFIX 0 C22 1 0.259176 0.582450 -0.130181 11.00000 0.03015 0.01905 = 0.02338 0.00182 0.00798 0.00078 AFIX 43 H22 2 0.306601 0.645120 -0.129806 11.00000 -1.20000 AFIX 0 C25 1 0.579078 0.697727 0.189685 11.00000 0.02432 0.05183 = 0.03265 0.01640 -0.00401 0.00624 AFIX 137 H25A 2 0.557211 0.621974 0.196334 11.00000 -1.50000 H25B 2 0.599495 0.732783 0.238188 11.00000 -1.50000 H25C 2 0.645811 0.699883 0.164154 11.00000 -1.50000 AFIX 0 C26 1 0.456927 0.724458 0.074726 11.00000 0.01880 0.01804 = 0.02519 0.00411 0.00453 -0.00138 C27 1 0.054644 0.720571 -0.073598 11.00000 0.01940 0.01649 = 0.02614 -0.00244 0.00531 0.00114 C28 1 -0.095304 0.704206 -0.176192 11.00000 0.02859 0.05080 = 0.04029 -0.00650 -0.00811 -0.01384 AFIX 137 H28A 2 -0.117911 0.731073 -0.226961 11.00000 -1.50000 H28B 2 -0.156786 0.720429 -0.147869 11.00000 -1.50000 H28C 2 -0.083124 0.625458 -0.177103 11.00000 -1.50000 AFIX 0 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM yan_exp302_1_0m in P2(1)/n REM R1 = 0.0385 for 4012 Fo > 4sig(Fo) and 0.0429 for all 4485 data REM 413 parameters refined using 66 restraints END WGHT 0.0482 1.3487 REM Highest difference peak 0.443, deepest hole -0.308, 1-sigma level 0.044 Q1 1 0.1666 0.3072 -0.2939 11.00000 0.05 0.44 Q2 1 0.0037 0.3244 -0.2623 11.00000 0.05 0.32 Q3 1 0.2550 1.0174 -0.0059 11.00000 0.05 0.22 Q4 1 0.4759 0.3506 0.2940 11.00000 0.05 0.21 Q5 1 0.3920 0.5009 0.3440 11.00000 0.05 0.21 Q6 1 0.0239 0.3933 -0.3056 11.00000 0.05 0.20 Q7 1 0.0834 0.4621 -0.3255 11.00000 0.05 0.20 Q8 1 0.1889 0.7585 -0.0137 11.00000 0.05 0.19 Q9 1 0.2818 0.3494 0.3063 11.00000 0.05 0.18 Q10 1 0.3368 0.8332 0.0494 11.00000 0.05 0.18 Q11 1 0.3158 0.7586 0.0103 11.00000 0.05 0.17 Q12 1 0.3968 0.7560 0.0533 11.00000 0.05 0.17 Q13 1 0.2027 0.4601 -0.1954 11.00000 0.05 0.16 Q14 1 0.3617 0.8332 0.0197 11.00000 0.05 0.16 Q15 1 0.6547 0.7427 0.1948 11.00000 0.05 0.16 Q16 1 -0.0507 0.3641 -0.2957 11.00000 0.05 0.16 Q17 1 0.1197 0.7415 -0.0656 11.00000 0.05 0.15 Q18 1 0.1541 0.8269 -0.0318 11.00000 0.05 0.15 Q19 1 0.1081 0.7628 -0.0471 11.00000 0.05 0.15 Q20 1 0.5576 0.6716 0.2381 11.00000 0.05 0.15 ; _shelx_res_checksum 94723 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group F1 F 0.3179(12) 0.4547(9) 0.3361(4) 0.076(2) Uani 0.472(18) 1 d . U P A 1 F2 F 0.4834(7) 0.4261(10) 0.3111(6) 0.073(2) Uani 0.472(18) 1 d . U P A 1 F3 F 0.3549(9) 0.3080(6) 0.2850(5) 0.0625(19) Uani 0.472(18) 1 d . U P A 1 F1A F 0.2814(6) 0.4255(8) 0.3259(5) 0.0648(16) Uani 0.528(18) 1 d . U P A 2 F2A F 0.4582(10) 0.4598(9) 0.3254(5) 0.085(2) Uani 0.528(18) 1 d . U P A 2 F3A F 0.3872(9) 0.3090(6) 0.2876(4) 0.0584(17) Uani 0.528(18) 1 d . U P A 2 F4 F 0.1499(5) 0.4000(4) -0.3222(2) 0.0857(16) Uani 0.594(6) 1 d . U P B 3 F5 F 0.1255(3) 0.2639(3) -0.2568(2) 0.0460(8) Uani 0.594(6) 1 d . U P B 3 F6 F -0.0091(3) 0.3763(3) -0.28373(18) 0.0779(13) Uani 0.594(6) 1 d . U P B 3 F4A F 0.0791(7) 0.2863(6) -0.2652(4) 0.089(2) Uani 0.406(6) 1 d . U P B 4 F5A F 0.0406(5) 0.4425(5) -0.3134(2) 0.0805(17) Uani 0.406(6) 1 d . U P B 4 F6A F 0.2043(4) 0.3789(5) -0.3105(3) 0.0484(11) Uani 0.406(6) 1 d . U P B 4 C23 C 0.36825(15) 0.41432(14) 0.28601(9) 0.0349(4) Uani 1 1 d . . . . . C24 C 0.11102(18) 0.37638(17) -0.26649(10) 0.0462(5) Uani 1 1 d . . . . . O1 O 0.48259(9) 0.75469(9) 0.14591(5) 0.0273(2) Uani 1 1 d . . . . . O2 O 0.51225(9) 0.66037(8) 0.04619(6) 0.0306(3) Uani 1 1 d . . . . . O3 O 0.00948(9) 0.65198(8) -0.04186(6) 0.0284(3) Uani 1 1 d . . . . . O4 O 0.01090(9) 0.75687(9) -0.14170(6) 0.0290(3) Uani 1 1 d . . . . . N1 N 0.25885(10) 0.60648(9) 0.00107(6) 0.0189(3) Uani 1 1 d . . . . . C1 C 0.25786(11) 0.72196(11) -0.00181(7) 0.0175(3) Uani 1 1 d . . . . . C2 C 0.35114(12) 0.78168(11) 0.03583(7) 0.0182(3) Uani 1 1 d . . . . . C3 C 0.34802(12) 0.89521(11) 0.03568(7) 0.0186(3) Uani 1 1 d . . . . . H3 H 0.4097 0.9343 0.0647 0.022 Uiso 1 1 calc R U . . . C4 C 0.25700(11) 0.95229(11) -0.00586(7) 0.0175(3) Uani 1 1 d . . . . . C5 C 0.16624(12) 0.89158(11) -0.04544(7) 0.0187(3) Uani 1 1 d . . . . . H5 H 0.1045 0.9284 -0.0760 0.022 Uiso 1 1 calc R U . . . C6 C 0.16337(12) 0.77893(11) -0.04146(7) 0.0183(3) Uani 1 1 d . . . . . C7 C 0.25345(11) 1.07675(11) -0.01030(7) 0.0202(3) Uani 1 1 d . . . . . C8 C 0.13685(13) 1.11855(12) 0.00535(9) 0.0285(3) Uani 1 1 d . . . . . H8A H 0.1356 1.1981 0.0029 0.043 Uiso 1 1 calc R U . . . H8AB H 0.1265 1.0951 0.0548 0.043 Uiso 1 1 calc R U . . . H8AC H 0.0740 1.0891 -0.0317 0.043 Uiso 1 1 calc R U . . . C9 C 0.26731(14) 1.11160(12) -0.08843(8) 0.0289(3) Uani 1 1 d . . . . . H9A H 0.2046 1.0801 -0.1246 0.043 Uiso 1 1 calc R U . . . H9AB H 0.3421 1.0860 -0.0986 0.043 Uiso 1 1 calc R U . . . H9AC H 0.2641 1.1910 -0.0920 0.043 Uiso 1 1 calc R U . . . C10 C 0.34985(14) 1.12899(12) 0.04550(9) 0.0305(4) Uani 1 1 d . . . . . H10A H 0.4253 1.1056 0.0351 0.046 Uiso 1 1 calc R U . . . H10B H 0.3423 1.1066 0.0957 0.046 Uiso 1 1 calc R U . . . H10C H 0.3438 1.2083 0.0415 0.046 Uiso 1 1 calc R U . . . C11 C 0.28118(12) 0.55471(11) 0.07099(7) 0.0189(3) Uani 1 1 d . . . . . C12 C 0.35183(12) 0.46309(11) 0.08175(8) 0.0212(3) Uani 1 1 d . . . . . H12 H 0.3817 0.4325 0.0414 0.025 Uiso 1 1 calc R U . . . C13 C 0.37833(13) 0.41682(11) 0.15136(8) 0.0240(3) Uani 1 1 d . . . . . H13 H 0.4262 0.3541 0.1588 0.029 Uiso 1 1 calc R U . . . C14 C 0.33519(13) 0.46184(12) 0.21056(8) 0.0242(3) Uani 1 1 d . . . . . C15 C 0.26385(13) 0.55236(12) 0.19968(8) 0.0254(3) Uani 1 1 d . . . . . H15 H 0.2339 0.5828 0.2400 0.031 Uiso 1 1 calc R U . . . C16 C 0.23628(13) 0.59826(11) 0.12999(8) 0.0230(3) Uani 1 1 d . . . . . H16 H 0.1866 0.6597 0.1224 0.028 Uiso 1 1 calc R U . . . C17 C 0.22755(12) 0.54590(11) -0.06470(7) 0.0184(3) Uani 1 1 d . . . . . C18 C 0.16012(12) 0.45252(11) -0.06527(8) 0.0214(3) Uani 1 1 d . . . . . H18 H 0.1390 0.4268 -0.0206 0.026 Uiso 1 1 calc R U . . . C19 C 0.12403(13) 0.39748(12) -0.13067(8) 0.0255(3) Uani 1 1 d . . . . . H19 H 0.0785 0.3336 -0.1309 0.031 Uiso 1 1 calc R U . . . C20 C 0.15381(14) 0.43485(12) -0.19626(8) 0.0280(3) Uani 1 1 d . . . . . C21 C 0.22154(14) 0.52750(12) -0.19583(8) 0.0284(3) Uani 1 1 d . . . . . H21 H 0.2421 0.5532 -0.2406 0.034 Uiso 1 1 calc R U . . . C22 C 0.25918(13) 0.58245(12) -0.13018(8) 0.0238(3) Uani 1 1 d . . . . . H22 H 0.3066 0.6451 -0.1298 0.029 Uiso 1 1 calc R U . . . C25 C 0.57908(14) 0.69773(15) 0.18969(9) 0.0373(4) Uani 1 1 d . . . . . H25A H 0.5572 0.6220 0.1963 0.056 Uiso 1 1 calc R U . . . H25B H 0.5995 0.7328 0.2382 0.056 Uiso 1 1 calc R U . . . H25C H 0.6458 0.6999 0.1642 0.056 Uiso 1 1 calc R U . . . C26 C 0.45693(12) 0.72446(11) 0.07473(8) 0.0206(3) Uani 1 1 d . . . . . C27 C 0.05464(12) 0.72057(11) -0.07360(8) 0.0205(3) Uani 1 1 d . . . . . C28 C -0.09530(15) 0.70421(16) -0.17619(10) 0.0416(4) Uani 1 1 d . . . . . H28A H -0.1179 0.7311 -0.2270 0.062 Uiso 1 1 calc R U . . . H28B H -0.1568 0.7204 -0.1479 0.062 Uiso 1 1 calc R U . . . H28C H -0.0831 0.6255 -0.1771 0.062 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.119(5) 0.093(4) 0.0180(17) 0.006(2) 0.016(3) 0.045(4) F2 0.050(2) 0.113(5) 0.045(3) 0.033(3) -0.025(2) -0.019(3) F3 0.087(4) 0.047(3) 0.042(2) 0.0314(19) -0.020(2) -0.036(3) F1A 0.069(3) 0.104(4) 0.026(3) 0.024(2) 0.0204(19) 0.012(2) F2A 0.100(5) 0.097(4) 0.039(3) 0.023(2) -0.037(3) -0.057(3) F3A 0.095(4) 0.049(3) 0.032(2) 0.0158(17) 0.014(2) 0.024(3) F4 0.141(4) 0.091(3) 0.0267(15) -0.0147(16) 0.020(2) -0.065(3) F5 0.0569(17) 0.0350(12) 0.0400(14) -0.0210(9) -0.0082(12) 0.0030(11) F6 0.0505(16) 0.107(2) 0.0606(18) -0.0422(17) -0.0345(13) 0.0184(16) F4A 0.135(5) 0.083(4) 0.046(2) -0.018(3) 0.007(4) -0.069(4) F5A 0.066(3) 0.120(4) 0.040(2) -0.024(2) -0.0333(18) 0.020(3) F6A 0.063(3) 0.060(2) 0.0210(18) -0.0198(14) 0.0029(17) 0.005(2) C23 0.0429(10) 0.0368(9) 0.0227(8) 0.0032(7) -0.0008(7) -0.0065(8) C24 0.0584(12) 0.0494(12) 0.0264(9) -0.0090(8) -0.0045(8) -0.0009(10) O1 0.0223(5) 0.0352(6) 0.0225(5) 0.0029(4) -0.0018(4) 0.0063(4) O2 0.0263(6) 0.0280(6) 0.0382(6) -0.0013(5) 0.0072(5) 0.0089(5) O3 0.0237(5) 0.0222(5) 0.0408(6) 0.0035(5) 0.0096(5) -0.0029(4) O4 0.0244(6) 0.0332(6) 0.0260(6) -0.0002(4) -0.0051(4) -0.0093(4) N1 0.0260(6) 0.0143(6) 0.0162(6) 0.0010(4) 0.0034(5) 0.0011(4) C1 0.0222(7) 0.0157(7) 0.0155(7) 0.0003(5) 0.0061(5) 0.0006(5) C2 0.0196(7) 0.0197(7) 0.0160(6) 0.0009(5) 0.0048(5) 0.0020(5) C3 0.0188(7) 0.0189(7) 0.0181(7) -0.0015(5) 0.0031(5) -0.0014(5) C4 0.0197(7) 0.0162(7) 0.0178(7) 0.0001(5) 0.0061(5) 0.0001(5) C5 0.0184(7) 0.0190(7) 0.0186(7) 0.0024(5) 0.0027(5) 0.0016(5) C6 0.0197(7) 0.0188(7) 0.0170(7) 0.0004(5) 0.0048(5) 0.0002(5) C7 0.0214(7) 0.0152(7) 0.0238(7) 0.0007(5) 0.0032(6) 0.0006(5) C8 0.0293(8) 0.0205(7) 0.0365(9) -0.0018(6) 0.0081(7) 0.0046(6) C9 0.0367(9) 0.0210(7) 0.0302(8) 0.0052(6) 0.0090(7) -0.0002(6) C10 0.0319(9) 0.0179(7) 0.0383(9) -0.0028(6) -0.0032(7) -0.0018(6) C11 0.0214(7) 0.0179(7) 0.0170(7) 0.0002(5) 0.0022(5) -0.0035(5) C12 0.0251(7) 0.0194(7) 0.0194(7) -0.0010(5) 0.0046(6) 0.0014(6) C13 0.0261(8) 0.0204(7) 0.0244(7) 0.0019(6) 0.0011(6) 0.0009(6) C14 0.0282(8) 0.0239(7) 0.0190(7) 0.0010(6) 0.0003(6) -0.0081(6) C15 0.0346(8) 0.0251(7) 0.0181(7) -0.0035(6) 0.0088(6) -0.0046(6) C16 0.0278(8) 0.0181(7) 0.0243(7) -0.0007(6) 0.0076(6) 0.0016(6) C17 0.0201(7) 0.0172(6) 0.0176(7) -0.0003(5) 0.0020(5) 0.0047(5) C18 0.0243(7) 0.0197(7) 0.0201(7) 0.0020(5) 0.0040(6) 0.0018(6) C19 0.0259(8) 0.0206(7) 0.0282(8) -0.0023(6) -0.0001(6) -0.0001(6) C20 0.0328(8) 0.0274(8) 0.0215(8) -0.0030(6) -0.0016(6) 0.0060(6) C21 0.0404(9) 0.0277(8) 0.0180(7) 0.0021(6) 0.0076(6) 0.0056(7) C22 0.0302(8) 0.0191(7) 0.0234(7) 0.0018(6) 0.0080(6) 0.0008(6) C25 0.0243(8) 0.0518(11) 0.0327(9) 0.0164(8) -0.0040(7) 0.0062(8) C26 0.0188(7) 0.0180(7) 0.0252(7) 0.0041(6) 0.0045(6) -0.0014(5) C27 0.0194(7) 0.0165(7) 0.0261(7) -0.0024(6) 0.0053(6) 0.0011(5) C28 0.0286(9) 0.0508(11) 0.0403(10) -0.0065(8) -0.0081(7) -0.0138(8) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F2A C23 F3A 107.2(5) . . ? F1 C23 F3 109.1(6) . . ? F1 C23 F2 105.8(5) . . ? F3 C23 F2 102.7(5) . . ? F2A C23 F1A 105.6(5) . . ? F3A C23 F1A 103.2(5) . . ? F1 C23 C14 116.0(4) . . ? F2A C23 C14 113.8(4) . . ? F3A C23 C14 115.0(3) . . ? F3 C23 C14 111.4(4) . . ? F2 C23 C14 110.8(4) . . ? F1A C23 C14 111.3(4) . . ? F4A C24 F5A 114.8(4) . . ? F4 C24 F6 108.7(3) . . ? F4 C24 F5 106.6(3) . . ? F6 C24 F5 97.1(3) . . ? F4A C24 F6A 107.6(5) . . ? F5A C24 F6A 93.9(3) . . ? F4A C24 C20 120.1(4) . . ? F4 C24 C20 119.4(2) . . ? F5A C24 C20 109.7(2) . . ? F6 C24 C20 111.93(18) . . ? F5 C24 C20 110.7(2) . . ? F6A C24 C20 107.2(2) . . ? C26 O1 C25 115.23(12) . . ? C27 O4 C28 114.68(12) . . ? C17 N1 C11 121.09(11) . . ? C17 N1 C1 119.81(10) . . ? C11 N1 C1 118.85(10) . . ? C2 C1 C6 118.22(13) . . ? C2 C1 N1 120.48(12) . . ? C6 C1 N1 121.29(12) . . ? C1 C2 C3 120.49(12) . . ? C1 C2 C26 120.07(12) . . ? C3 C2 C26 119.41(12) . . ? C4 C3 C2 121.60(12) . . ? C4 C3 H3 119.2 . . ? C2 C3 H3 119.2 . . ? C3 C4 C5 117.23(12) . . ? C3 C4 C7 123.04(12) . . ? C5 C4 C7 119.72(12) . . ? C6 C5 C4 122.02(12) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C5 C6 C1 120.14(12) . . ? C5 C6 C27 119.12(12) . . ? C1 C6 C27 120.49(12) . . ? C10 C7 C9 108.78(12) . . ? C10 C7 C4 112.00(11) . . ? C9 C7 C4 108.84(11) . . ? C10 C7 C8 108.21(12) . . ? C9 C7 C8 108.97(12) . . ? C4 C7 C8 109.98(11) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8AB 109.5 . . ? H8A C8 H8AB 109.5 . . ? C7 C8 H8AC 109.5 . . ? H8A C8 H8AC 109.5 . . ? H8AB C8 H8AC 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9AB 109.5 . . ? H9A C9 H9AB 109.5 . . ? C7 C9 H9AC 109.5 . . ? H9A C9 H9AC 109.5 . . ? H9AB C9 H9AC 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 119.89(13) . . ? C16 C11 N1 119.78(12) . . ? C12 C11 N1 120.27(12) . . ? C13 C12 C11 119.75(13) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.22(13) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C15 C14 C13 120.02(13) . . ? C15 C14 C23 120.09(14) . . ? C13 C14 C23 119.86(14) . . ? C16 C15 C14 119.91(13) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 120.18(13) . . ? C15 C16 H16 119.9 . . ? C11 C16 H16 119.9 . . ? C22 C17 C18 119.75(13) . . ? C22 C17 N1 119.89(12) . . ? C18 C17 N1 120.29(12) . . ? C19 C18 C17 119.94(13) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C20 120.40(14) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C19 C20 C21 119.82(13) . . ? C19 C20 C24 119.57(15) . . ? C21 C20 C24 120.60(15) . . ? C22 C21 C20 120.06(14) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C17 120.02(14) . . ? C21 C22 H22 120.0 . . ? C17 C22 H22 120.0 . . ? O1 C25 H25A 109.5 . . ? O1 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? O1 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O2 C26 O1 124.19(13) . . ? O2 C26 C2 124.68(13) . . ? O1 C26 C2 111.13(11) . . ? O3 C27 O4 123.84(13) . . ? O3 C27 C6 124.47(13) . . ? O4 C27 C6 111.65(11) . . ? O4 C28 H28A 109.5 . . ? O4 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? O4 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 C23 1.277(9) . ? F2 C23 1.356(8) . ? F3 C23 1.317(8) . ? F1A C23 1.361(7) . ? F2A C23 1.296(8) . ? F3A C23 1.315(7) . ? F4 C24 1.224(4) . ? F5 C24 1.402(4) . ? F6 C24 1.388(4) . ? F4A C24 1.172(7) . ? F5A C24 1.355(5) . ? F6A C24 1.469(6) . ? C23 C14 1.490(2) . ? C24 C20 1.484(2) . ? O1 C26 1.3403(18) . ? O1 C25 1.4484(18) . ? O2 C26 1.1980(17) . ? O3 C27 1.1998(17) . ? O4 C27 1.3411(18) . ? O4 C28 1.4474(18) . ? N1 C17 1.4110(17) . ? N1 C11 1.4150(17) . ? N1 C1 1.4218(18) . ? C1 C2 1.3958(19) . ? C1 C6 1.4021(19) . ? C2 C3 1.3974(19) . ? C2 C26 1.4945(19) . ? C3 C4 1.3886(19) . ? C3 H3 0.9500 . ? C4 C5 1.3953(19) . ? C4 C7 1.5338(18) . ? C5 C6 1.3887(19) . ? C5 H5 0.9500 . ? C6 C27 1.4917(19) . ? C7 C10 1.528(2) . ? C7 C9 1.5315(19) . ? C7 C8 1.5339(19) . ? C8 H8A 0.9800 . ? C8 H8AB 0.9800 . ? C8 H8AC 0.9800 . ? C9 H9A 0.9800 . ? C9 H9AB 0.9800 . ? C9 H9AC 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.3910(19) . ? C11 C12 1.3924(19) . ? C12 C13 1.383(2) . ? C12 H12 0.9500 . ? C13 C14 1.391(2) . ? C13 H13 0.9500 . ? C14 C15 1.386(2) . ? C15 C16 1.383(2) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C22 1.3922(19) . ? C17 C18 1.394(2) . ? C18 C19 1.378(2) . ? C18 H18 0.9500 . ? C19 C20 1.388(2) . ? C19 H19 0.9500 . ? C20 C21 1.389(2) . ? C21 C22 1.384(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ?