#------------------------------------------------------------------------------ #$Date: 2023-11-24 02:38:02 +0200 (Fri, 24 Nov 2023) $ #$Revision: 287767 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247787.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_7247787 loop_ _publ_author_name 'Lamba, Manisha' 'Singh, Prasoon Raj' 'Bhatt, Shubham' 'Goswami, Avijit' _publ_section_title ; Metal- and Additive-Free TfOH Catalyzed Chemoselective O- and S-Trifluoroethylation of Oxindoles, Isoindolines and Thioxindoles ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D3GC03702A _journal_year 2023 _chemical_formula_moiety '2(C17 H13 F3 N O)' _chemical_formula_sum 'C34 H26 F6 N2 O2' _chemical_formula_weight 608.57 _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 dual _audit_creation_date 2023-08-10 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2023-08-11 deposited with the CCDC. 2023-11-23 downloaded from the CCDC. ; _cell_angle_alpha 68.976(2) _cell_angle_beta 87.671(3) _cell_angle_gamma 69.921(2) _cell_formula_units_Z 2 _cell_length_a 10.0648(8) _cell_length_b 11.6308(8) _cell_length_c 13.8611(10) _cell_measurement_reflns_used 8192 _cell_measurement_temperature 298 _cell_measurement_theta_max 26.360 _cell_measurement_theta_min 2.541 _cell_volume 1416.21(18) _computing_cell_refinement 'SAINT V8.40B (?, 2016)' _computing_data_reduction 'SAINT V8.40B (?, 2016)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'SHELXT (Sheldrick, 2015)' _diffrn_ambient_temperature 298 _diffrn_detector 'Bruker APEX2 area detector' _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker APEX2 microsource' _diffrn_measurement_method '\w and \f scans' _diffrn_radiation_monochromator 'mirror optics' _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0577 _diffrn_reflns_av_unetI/netI 0.0585 _diffrn_reflns_Laue_measured_fraction_full 0.993 _diffrn_reflns_Laue_measured_fraction_max 0.992 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 18765 _diffrn_reflns_point_group_measured_fraction_full 0.993 _diffrn_reflns_point_group_measured_fraction_max 0.992 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.428 _diffrn_reflns_theta_min 2.004 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_current 1.0 _diffrn_source_power 0.05 _diffrn_source_type 'Incoatec I\ms' _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.4714 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1468 before and 0.0974 after correction. The Ratio of minimum to maximum transmission is 0.6324. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.427 _exptl_crystal_description block _exptl_crystal_F_000 628 _exptl_crystal_size_max 0.123 _exptl_crystal_size_mid 0.104 _exptl_crystal_size_min 0.098 _refine_diff_density_max 0.434 _refine_diff_density_min -0.478 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 397 _refine_ls_number_reflns 5794 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.033 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0626 _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^)+(0.1047P)^2^+0.3412P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1794 _refine_ls_wR_factor_ref 0.1917 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4679 _reflns_number_total 5794 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03702a2.cif _cod_data_source_block agml_1104_0m _cod_database_code 7247787 _shelx_shelxl_version_number 2019/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.989 _shelx_estimated_absorpt_t_min 0.986 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C2'(H2'A,H2'B) 2.b Aromatic/amide H refined with riding coordinates: N1'(H1'), N1(H1), C8(H8), C7(H7), C5(H5), C11(H11), C13(H13), C16(H16), C15(H15), C14(H14), C9(H9), C10(H10), C8'(H8'), C7'(H7'), C5'(H5'), C11'(H11'), C13'(H13'), C14'(H14'), C16'(H16'), C9'(H9'), C10'(H10'), C15'(H15') ; _shelx_res_file ; TITL AGML_1104_0m_a.res in P-1 agml_1104_0m.res created by SHELXL-2019/1 at 09:53:45 on 10-Aug-2023 CELL 0.71073 10.0648 11.6308 13.8611 68.976 87.671 69.921 ZERR 2 0.0008 0.0008 0.001 0.002 0.003 0.002 LATT 1 SFAC C H F N O UNIT 68 52 12 4 4 L.S. 4 PLAN 5 0 0 SIZE 0.104 0.098 0.123 TEMP 24.85 CONF LIST 6 HTAB BOND $H fmap 2 acta MORE -1 REM REM REM WGHT 0.104700 0.341200 FVAR 0.38861 F2 3 0.426393 0.335815 0.559179 11.00000 0.17146 0.11763 = 0.04484 -0.04446 0.01237 -0.06621 F1' 3 0.087364 0.545449 0.597910 11.00000 0.14688 0.07052 = 0.07974 -0.02876 0.01648 -0.05543 F3 3 0.255767 0.363253 0.454342 11.00000 0.08192 0.13058 = 0.13126 -0.07950 0.03723 -0.04701 F2' 3 0.229016 0.648585 0.544592 11.00000 0.06924 0.12361 = 0.12635 -0.06924 0.02696 -0.03687 F3' 3 0.052920 0.682911 0.442527 11.00000 0.13439 0.12017 = 0.05012 -0.05030 0.01505 -0.05516 F1 3 0.389288 0.474929 0.404925 11.00000 0.16267 0.07158 = 0.07141 -0.03175 0.02937 -0.05986 O1' 5 0.036302 0.740570 0.677286 11.00000 0.07773 0.07015 = 0.03423 -0.02243 0.00761 -0.04380 O1 5 0.455459 0.278393 0.323795 11.00000 0.07513 0.06513 = 0.03908 -0.02589 0.00746 -0.04031 N1' 4 0.148894 0.895888 0.636025 11.00000 0.05922 0.06315 = 0.03114 -0.01222 0.00448 -0.03133 AFIX 43 H1' 2 0.147713 0.916470 0.569876 11.00000 -1.20000 AFIX 0 N1 4 0.343761 0.122595 0.366184 11.00000 0.05334 0.06164 = 0.03126 -0.01717 0.00639 -0.02732 AFIX 43 H1 2 0.336975 0.108910 0.431110 11.00000 -1.20000 AFIX 0 C8 1 0.530720 0.399457 -0.155477 11.00000 0.06675 0.06946 = 0.04636 -0.01786 0.01791 -0.03748 AFIX 43 H8 2 0.602196 0.426022 -0.190461 11.00000 -1.20000 AFIX 0 C7 1 0.531884 0.367812 -0.049918 11.00000 0.04896 0.04890 = 0.04415 -0.01408 0.00507 -0.02526 AFIX 43 H7 2 0.602838 0.375580 -0.014427 11.00000 -1.20000 AFIX 0 C5 1 0.434487 0.293107 0.116920 11.00000 0.04544 0.04391 = 0.03960 -0.01853 0.00501 -0.02083 AFIX 43 H5 2 0.479480 0.337857 0.139551 11.00000 -1.20000 AFIX 0 C11 1 0.319518 0.318886 -0.051436 11.00000 0.04568 0.05223 = 0.04563 -0.01883 0.00524 -0.02342 AFIX 43 H11 2 0.247694 0.292354 -0.017020 11.00000 -1.20000 AFIX 0 C4 1 0.386448 0.210569 0.192915 11.00000 0.04217 0.04405 = 0.03561 -0.01774 0.00376 -0.01772 C12 1 0.325168 0.109617 0.202303 11.00000 0.04056 0.04555 = 0.03698 -0.01573 0.00368 -0.01957 C13 1 0.302951 0.049701 0.137317 11.00000 0.06069 0.05609 = 0.04274 -0.02183 0.00336 -0.02835 AFIX 43 H13 2 0.321941 0.077944 0.068191 11.00000 -1.20000 AFIX 0 C1 1 0.390607 0.356967 0.461487 11.00000 0.08883 0.07458 = 0.04168 -0.02676 0.01077 -0.04513 C6' 1 0.074119 0.687387 0.998323 11.00000 0.03704 0.04489 = 0.03666 -0.01723 0.00493 -0.02070 C3 1 0.395043 0.202672 0.301101 11.00000 0.04554 0.05009 = 0.03871 -0.02082 0.00376 -0.01969 C2 1 0.488117 0.250714 0.430190 11.00000 0.06937 0.07235 = 0.04495 -0.02424 -0.00512 -0.03448 AFIX 23 H2A 2 0.585540 0.243614 0.441591 11.00000 -1.20000 H2B 2 0.478771 0.167365 0.472214 11.00000 -1.20000 AFIX 0 C16 1 0.245690 -0.038699 0.346435 11.00000 0.06352 0.06417 = 0.04274 -0.00772 0.00235 -0.03638 AFIX 43 H16 2 0.225467 -0.067075 0.415261 11.00000 -1.20000 AFIX 0 C15 1 0.221795 -0.095329 0.279194 11.00000 0.08125 0.06703 = 0.06012 -0.01033 -0.00300 -0.04939 AFIX 43 H15 2 0.184938 -0.162695 0.303382 11.00000 -1.20000 AFIX 0 C14 1 0.251768 -0.053392 0.177267 11.00000 0.08170 0.06203 = 0.05791 -0.02387 -0.00153 -0.04053 AFIX 43 H14 2 0.237523 -0.094759 0.134382 11.00000 -1.20000 AFIX 0 C17 1 0.300668 0.061511 0.307694 11.00000 0.04310 0.05138 = 0.03726 -0.01406 0.00300 -0.02187 C9 1 0.423866 0.392009 -0.209922 11.00000 0.08740 0.07778 = 0.03641 -0.01939 0.00815 -0.03863 AFIX 43 H9 2 0.423455 0.413360 -0.281340 11.00000 -1.20000 AFIX 0 C10 1 0.317823 0.352772 -0.157884 11.00000 0.06703 0.06809 = 0.04397 -0.01821 -0.00662 -0.03103 AFIX 43 H10 2 0.244949 0.349094 -0.194510 11.00000 -1.20000 AFIX 0 C8' 1 0.102160 0.532643 1.174537 11.00000 0.06007 0.05143 = 0.03884 -0.01027 0.00404 -0.02150 AFIX 43 H8' 2 0.124542 0.446330 1.220873 11.00000 -1.20000 AFIX 0 C7' 1 0.104621 0.559021 1.069304 11.00000 0.04916 0.04440 = 0.04163 -0.01846 0.00667 -0.02029 AFIX 43 H7' 2 0.126971 0.490134 1.045288 11.00000 -1.20000 AFIX 0 C5' 1 0.076233 0.710111 0.887310 11.00000 0.05295 0.04783 = 0.03687 -0.01834 0.00500 -0.02621 AFIX 43 H5' 2 0.044830 0.655322 0.866628 11.00000 -1.20000 AFIX 0 C11' 1 0.035496 0.789242 1.036340 11.00000 0.04538 0.04523 = 0.04553 -0.01950 0.00620 -0.01903 AFIX 43 H11' 2 0.012033 0.875876 0.990415 11.00000 -1.20000 AFIX 0 C4' 1 0.116588 0.797982 0.810785 11.00000 0.04676 0.04355 = 0.03408 -0.01586 0.00315 -0.01988 C3' 1 0.101677 0.812059 0.700914 11.00000 0.05180 0.05292 = 0.03692 -0.01815 0.00449 -0.02448 C2' 1 0.001750 0.770550 0.570697 11.00000 0.06641 0.06950 = 0.03779 -0.02229 -0.00088 -0.03205 AFIX 23 H2'A 2 0.017209 0.851093 0.528875 11.00000 -1.20000 H2'B 2 -0.097661 0.783818 0.558883 11.00000 -1.20000 AFIX 0 C13' 1 0.237753 0.930653 0.874015 11.00000 0.04452 0.04606 = 0.04414 -0.02054 0.00346 -0.01602 AFIX 43 H13' 2 0.228107 0.894889 0.944478 11.00000 -1.20000 AFIX 0 C14' 1 0.305290 1.022483 0.837347 11.00000 0.05081 0.05148 = 0.06510 -0.02861 0.00398 -0.02266 AFIX 43 H14' 2 0.340278 1.048494 0.883961 11.00000 -1.20000 AFIX 0 C16' 1 0.272787 1.037683 0.661136 11.00000 0.05537 0.05441 = 0.04903 -0.00659 0.00356 -0.02743 AFIX 43 H16' 2 0.286175 1.071579 0.591202 11.00000 -1.20000 AFIX 0 C1' 1 0.091953 0.660743 0.540048 11.00000 0.07616 0.07336 = 0.04439 -0.02498 0.00993 -0.03973 C17' 1 0.203485 0.947214 0.697255 11.00000 0.04426 0.04589 = 0.03950 -0.00950 0.00123 -0.01805 C9' 1 0.066515 0.634216 1.211138 11.00000 0.05763 0.07425 = 0.03554 -0.02390 0.00779 -0.02953 AFIX 43 H9' 2 0.065858 0.616458 1.282102 11.00000 -1.20000 AFIX 0 C10' 1 0.031867 0.762211 1.141932 11.00000 0.04786 0.06105 = 0.05227 -0.03540 0.01145 -0.02421 AFIX 43 H10' 2 0.005874 0.830848 1.166429 11.00000 -1.20000 AFIX 0 C12' 1 0.185214 0.893621 0.803460 11.00000 0.03993 0.03946 = 0.03847 -0.01381 0.00326 -0.01441 C15' 1 0.321143 1.075462 0.733115 11.00000 0.05389 0.04959 = 0.06672 -0.01324 0.00333 -0.02784 AFIX 43 H15' 2 0.365120 1.137752 0.710616 11.00000 -1.20000 AFIX 0 C6 1 0.427699 0.324027 0.004948 11.00000 0.04337 0.03816 = 0.03669 -0.01519 0.00568 -0.01670 HKLF 4 REM AGML_1104_0m_a.res in P-1 REM wR2 = 0.1917, GooF = S = 1.033, Restrained GooF = 1.033 for all data REM R1 = 0.0626 for 4679 Fo > 4sig(Fo) and 0.0737 for all 5794 data REM 397 parameters refined using 0 restraints END WGHT 0.1047 0.3412 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y+1, -z+1 HTAB C2 F2'_$1 EQIV $2 -x, -y+1, -z+1 HTAB C2' N1_$2 REM Highest difference peak 0.434, deepest hole -0.478, 1-sigma level 0.049 Q1 1 0.5812 0.3657 0.4370 11.00000 0.05 0.43 Q2 1 -0.0690 0.6177 0.5753 11.00000 0.05 0.42 Q3 1 0.4066 0.2490 0.4499 11.00000 0.05 0.26 Q4 1 0.2737 0.0179 0.3296 11.00000 0.05 0.24 Q5 1 0.2373 0.9795 0.6728 11.00000 0.05 0.23 ; _shelx_res_checksum 9727 _olex2_submission_special_instructions 'No special instructions were received' 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 F2 F 0.4264(2) 0.33581(19) 0.55918(11) 0.1028(6) Uani 1 1 d . . . . . F1' F 0.0874(2) 0.54545(15) 0.59791(13) 0.0941(5) Uani 1 1 d . . . . . F3 F 0.25577(19) 0.3633(2) 0.45434(16) 0.1035(6) Uani 1 1 d . . . . . F2' F 0.22902(18) 0.64859(19) 0.54459(15) 0.0993(6) Uani 1 1 d . . . . . F3' F 0.0529(2) 0.68291(18) 0.44253(11) 0.0933(5) Uani 1 1 d . . . . . F1 F 0.3893(2) 0.47493(15) 0.40493(12) 0.0956(6) Uani 1 1 d . . . . . O1' O 0.03630(17) 0.74057(15) 0.67729(10) 0.0548(4) Uani 1 1 d . . . . . O1 O 0.45546(16) 0.27839(14) 0.32379(10) 0.0535(4) Uani 1 1 d . . . . . N1' N 0.14889(18) 0.89589(17) 0.63603(11) 0.0499(4) Uani 1 1 d . . . . . H1' H 0.147713 0.916470 0.569876 0.060 Uiso 1 1 calc R U . . . N1 N 0.34376(17) 0.12260(16) 0.36618(11) 0.0468(4) Uani 1 1 d . . . . . H1 H 0.336975 0.108910 0.431110 0.056 Uiso 1 1 calc R U . . . C8 C 0.5307(2) 0.3995(2) -0.15548(15) 0.0585(5) Uani 1 1 d . . . . . H8 H 0.602196 0.426022 -0.190461 0.070 Uiso 1 1 calc R U . . . C7 C 0.5319(2) 0.36781(18) -0.04992(14) 0.0460(4) Uani 1 1 d . . . . . H7 H 0.602838 0.375580 -0.014427 0.055 Uiso 1 1 calc R U . . . C5 C 0.43449(19) 0.29311(17) 0.11692(13) 0.0407(4) Uani 1 1 d . . . . . H5 H 0.479480 0.337857 0.139551 0.049 Uiso 1 1 calc R U . . . C11 C 0.3195(2) 0.31889(18) -0.05144(14) 0.0459(4) Uani 1 1 d . . . . . H11 H 0.247694 0.292354 -0.017020 0.055 Uiso 1 1 calc R U . . . C4 C 0.38645(18) 0.21057(17) 0.19292(13) 0.0390(4) Uani 1 1 d . . . . . C12 C 0.32517(18) 0.10962(17) 0.20230(13) 0.0396(4) Uani 1 1 d . . . . . C13 C 0.3030(2) 0.04970(19) 0.13732(15) 0.0499(5) Uani 1 1 d . . . . . H13 H 0.321941 0.077944 0.068191 0.060 Uiso 1 1 calc R U . . . C1 C 0.3906(3) 0.3570(2) 0.46149(16) 0.0623(6) Uani 1 1 d . . . . . C6' C 0.07412(17) 0.68739(17) 0.99832(13) 0.0372(4) Uani 1 1 d . . . . . C3 C 0.39504(19) 0.20267(18) 0.30110(13) 0.0427(4) Uani 1 1 d . . . . . C2 C 0.4881(2) 0.2507(2) 0.43019(15) 0.0584(5) Uani 1 1 d . . . . . H2A H 0.585540 0.243614 0.441591 0.070 Uiso 1 1 calc R U . . . H2B H 0.478771 0.167365 0.472214 0.070 Uiso 1 1 calc R U . . . C16 C 0.2457(2) -0.0387(2) 0.34644(15) 0.0564(5) Uani 1 1 d . . . . . H16 H 0.225467 -0.067075 0.415261 0.068 Uiso 1 1 calc R U . . . C15 C 0.2218(3) -0.0953(2) 0.27919(18) 0.0665(6) Uani 1 1 d . . . . . H15 H 0.184938 -0.162695 0.303382 0.080 Uiso 1 1 calc R U . . . C14 C 0.2518(3) -0.0534(2) 0.17727(17) 0.0622(6) Uani 1 1 d . . . . . H14 H 0.237523 -0.094759 0.134382 0.075 Uiso 1 1 calc R U . . . C17 C 0.30067(19) 0.06151(18) 0.30769(13) 0.0431(4) Uani 1 1 d . . . . . C9 C 0.4239(3) 0.3920(2) -0.20992(16) 0.0651(6) Uani 1 1 d . . . . . H9 H 0.423455 0.413360 -0.281340 0.078 Uiso 1 1 calc R U . . . C10 C 0.3178(2) 0.3528(2) -0.15788(15) 0.0580(5) Uani 1 1 d . . . . . H10 H 0.244949 0.349094 -0.194510 0.070 Uiso 1 1 calc R U . . . C8' C 0.1022(2) 0.5326(2) 1.17454(14) 0.0514(5) Uani 1 1 d . . . . . H8' H 0.124542 0.446330 1.220873 0.062 Uiso 1 1 calc R U . . . C7' C 0.10462(19) 0.55902(17) 1.06930(13) 0.0433(4) Uani 1 1 d . . . . . H7' H 0.126971 0.490134 1.045288 0.052 Uiso 1 1 calc R U . . . C5' C 0.0762(2) 0.71011(18) 0.88731(13) 0.0427(4) Uani 1 1 d . . . . . H5' H 0.044830 0.655322 0.866628 0.051 Uiso 1 1 calc R U . . . C11' C 0.03550(19) 0.78924(18) 1.03634(14) 0.0437(4) Uani 1 1 d . . . . . H11' H 0.012033 0.875876 0.990415 0.052 Uiso 1 1 calc R U . . . C4' C 0.11659(19) 0.79798(17) 0.81079(13) 0.0399(4) Uani 1 1 d . . . . . C3' C 0.1017(2) 0.81206(19) 0.70091(13) 0.0450(4) Uani 1 1 d . . . . . C2' C 0.0018(2) 0.7706(2) 0.57070(14) 0.0547(5) Uani 1 1 d . . . . . H2'A H 0.017209 0.851093 0.528875 0.066 Uiso 1 1 calc R U . . . H2'B H -0.097661 0.783818 0.558883 0.066 Uiso 1 1 calc R U . . . C13' C 0.23775(19) 0.93065(17) 0.87401(14) 0.0437(4) Uani 1 1 d . . . . . H13' H 0.228107 0.894889 0.944478 0.052 Uiso 1 1 calc R U . . . C14' C 0.3053(2) 1.02248(19) 0.83735(17) 0.0523(5) Uani 1 1 d . . . . . H14' H 0.340278 1.048494 0.883961 0.063 Uiso 1 1 calc R U . . . C16' C 0.2728(2) 1.0377(2) 0.66114(16) 0.0543(5) Uani 1 1 d . . . . . H16' H 0.286175 1.071579 0.591202 0.065 Uiso 1 1 calc R U . . . C1' C 0.0920(3) 0.6607(2) 0.54005(16) 0.0600(5) Uani 1 1 d . . . . . C17' C 0.20349(19) 0.94721(18) 0.69726(14) 0.0444(4) Uani 1 1 d . . . . . C9' C 0.0665(2) 0.6342(2) 1.21114(14) 0.0530(5) Uani 1 1 d . . . . . H9' H 0.065858 0.616458 1.282102 0.064 Uiso 1 1 calc R U . . . C10' C 0.0319(2) 0.7622(2) 1.14193(15) 0.0482(4) Uani 1 1 d . . . . . H10' H 0.005874 0.830848 1.166429 0.058 Uiso 1 1 calc R U . . . C12' C 0.18521(18) 0.89362(16) 0.80346(13) 0.0393(4) Uani 1 1 d . . . . . C15' C 0.3211(2) 1.0755(2) 0.73312(17) 0.0564(5) Uani 1 1 d . . . . . H15' H 0.365120 1.137752 0.710616 0.068 Uiso 1 1 calc R U . . . C6 C 0.42770(18) 0.32403(16) 0.00495(13) 0.0384(4) Uani 1 1 d . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F2 0.1715(18) 0.1176(13) 0.0448(7) -0.0445(8) 0.0124(9) -0.0662(13) F1' 0.1469(16) 0.0705(9) 0.0797(10) -0.0288(8) 0.0165(10) -0.0554(10) F3 0.0819(11) 0.1306(15) 0.1313(15) -0.0795(13) 0.0372(10) -0.0470(11) F2' 0.0692(10) 0.1236(14) 0.1264(15) -0.0692(12) 0.0270(10) -0.0369(9) F3' 0.1344(15) 0.1202(13) 0.0501(8) -0.0503(8) 0.0151(8) -0.0552(11) F1 0.1627(17) 0.0716(9) 0.0714(9) -0.0317(8) 0.0294(10) -0.0599(10) O1' 0.0777(10) 0.0702(9) 0.0342(7) -0.0224(6) 0.0076(6) -0.0438(8) O1 0.0751(10) 0.0651(9) 0.0391(7) -0.0259(6) 0.0075(6) -0.0403(7) N1' 0.0592(10) 0.0632(10) 0.0311(7) -0.0122(7) 0.0045(7) -0.0313(8) N1 0.0533(9) 0.0616(10) 0.0313(7) -0.0172(7) 0.0064(6) -0.0273(7) C8 0.0668(13) 0.0695(13) 0.0464(10) -0.0179(9) 0.0179(9) -0.0375(11) C7 0.0490(10) 0.0489(10) 0.0442(9) -0.0141(8) 0.0051(8) -0.0253(8) C5 0.0454(9) 0.0439(9) 0.0396(9) -0.0185(7) 0.0050(7) -0.0208(7) C11 0.0457(10) 0.0522(10) 0.0456(9) -0.0188(8) 0.0052(8) -0.0234(8) C4 0.0422(9) 0.0440(9) 0.0356(8) -0.0177(7) 0.0038(7) -0.0177(7) C12 0.0406(9) 0.0456(9) 0.0370(8) -0.0157(7) 0.0037(7) -0.0196(7) C13 0.0607(12) 0.0561(11) 0.0427(9) -0.0218(8) 0.0034(8) -0.0284(9) C1 0.0888(17) 0.0746(14) 0.0417(10) -0.0268(10) 0.0108(10) -0.0451(13) C6' 0.0370(8) 0.0449(9) 0.0367(8) -0.0172(7) 0.0049(7) -0.0207(7) C3 0.0455(10) 0.0501(10) 0.0387(9) -0.0208(8) 0.0038(7) -0.0197(8) C2 0.0694(14) 0.0723(13) 0.0450(10) -0.0242(10) -0.0051(9) -0.0345(11) C16 0.0635(13) 0.0642(12) 0.0427(10) -0.0077(9) 0.0023(9) -0.0364(10) C15 0.0813(16) 0.0670(13) 0.0601(13) -0.0103(11) -0.0030(11) -0.0494(12) C14 0.0817(15) 0.0620(12) 0.0579(12) -0.0239(10) -0.0015(11) -0.0405(11) C17 0.0431(9) 0.0514(10) 0.0373(9) -0.0141(7) 0.0030(7) -0.0219(8) C9 0.0874(17) 0.0778(15) 0.0364(10) -0.0194(10) 0.0081(10) -0.0386(13) C10 0.0670(13) 0.0681(13) 0.0440(10) -0.0182(9) -0.0066(9) -0.0310(10) C8' 0.0601(12) 0.0514(10) 0.0388(9) -0.0103(8) 0.0040(8) -0.0215(9) C7' 0.0492(10) 0.0444(9) 0.0416(9) -0.0185(7) 0.0067(7) -0.0203(8) C5' 0.0530(10) 0.0478(9) 0.0369(9) -0.0183(7) 0.0050(7) -0.0262(8) C11' 0.0454(10) 0.0452(9) 0.0455(9) -0.0195(8) 0.0062(7) -0.0190(8) C4' 0.0468(10) 0.0436(9) 0.0341(8) -0.0159(7) 0.0031(7) -0.0199(7) C3' 0.0518(10) 0.0529(10) 0.0369(9) -0.0182(8) 0.0045(8) -0.0245(8) C2' 0.0664(13) 0.0695(13) 0.0378(9) -0.0223(9) -0.0009(9) -0.0321(10) C13' 0.0445(10) 0.0461(9) 0.0441(9) -0.0205(8) 0.0035(7) -0.0160(8) C14' 0.0508(11) 0.0515(10) 0.0651(12) -0.0286(9) 0.0040(9) -0.0227(9) C16' 0.0554(12) 0.0544(11) 0.0490(11) -0.0066(9) 0.0036(9) -0.0274(9) C1' 0.0762(15) 0.0734(14) 0.0444(11) -0.0250(10) 0.0099(10) -0.0397(12) C17' 0.0443(10) 0.0459(9) 0.0395(9) -0.0095(7) 0.0012(7) -0.0180(8) C9' 0.0576(12) 0.0742(13) 0.0355(9) -0.0239(9) 0.0078(8) -0.0295(10) C10' 0.0479(10) 0.0610(11) 0.0523(10) -0.0354(9) 0.0115(8) -0.0242(9) C12' 0.0399(9) 0.0395(8) 0.0385(8) -0.0138(7) 0.0033(7) -0.0144(7) C15' 0.0539(12) 0.0496(11) 0.0667(13) -0.0132(9) 0.0033(10) -0.0278(9) C6 0.0434(9) 0.0382(8) 0.0367(8) -0.0152(7) 0.0057(7) -0.0167(7) 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' F F 0.0171 0.0103 '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' 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 C3' O1' C2' 117.60(15) . . ? C3 O1 C2 117.41(15) . . ? C3' N1' H1' 127.6 . . ? C3' N1' C17' 104.75(15) . . ? C17' N1' H1' 127.6 . . ? C3 N1 H1 127.6 . . ? C3 N1 C17 104.74(14) . . ? C17 N1 H1 127.6 . . ? C7 C8 H8 119.8 . . ? C7 C8 C9 120.34(19) . . ? C9 C8 H8 119.8 . . ? C8 C7 H7 119.5 . . ? C8 C7 C6 120.91(18) . . ? C6 C7 H7 119.5 . . ? C4 C5 H5 114.6 . . ? C4 C5 C6 130.79(16) . . ? C6 C5 H5 114.6 . . ? C10 C11 H11 119.6 . . ? C10 C11 C6 120.80(17) . . ? C6 C11 H11 119.6 . . ? C5 C4 C12 136.80(16) . . ? C5 C4 C3 121.44(16) . . ? C12 C4 C3 101.70(14) . . ? C13 C12 C4 135.22(16) . . ? C13 C12 C17 119.35(17) . . ? C17 C12 C4 105.05(15) . . ? C12 C13 H13 120.6 . . ? C12 C13 C14 118.85(18) . . ? C14 C13 H13 120.6 . . ? F2 C1 F3 108.0(2) . . ? F2 C1 C2 110.2(2) . . ? F3 C1 C2 111.46(19) . . ? F1 C1 F2 107.05(19) . . ? F1 C1 F3 105.5(2) . . ? F1 C1 C2 114.3(2) . . ? C7' C6' C5' 118.83(15) . . ? C11' C6' C7' 118.15(15) . . ? C11' C6' C5' 122.94(16) . . ? O1 C3 C4 118.56(15) . . ? N1 C3 O1 125.54(16) . . ? N1 C3 C4 115.89(16) . . ? O1 C2 C1 109.97(18) . . ? O1 C2 H2A 109.7 . . ? O1 C2 H2B 109.7 . . ? C1 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C15 C16 H16 121.1 . . ? C17 C16 H16 121.1 . . ? C17 C16 C15 117.88(19) . . ? C16 C15 H15 119.5 . . ? C14 C15 C16 121.1(2) . . ? C14 C15 H15 119.5 . . ? C13 C14 H14 119.4 . . ? C15 C14 C13 121.2(2) . . ? C15 C14 H14 119.4 . . ? C12 C17 N1 112.50(15) . . ? C16 C17 N1 125.95(16) . . ? C16 C17 C12 121.50(17) . . ? C8 C9 H9 120.1 . . ? C10 C9 C8 119.73(18) . . ? C10 C9 H9 120.1 . . ? C11 C10 H10 119.9 . . ? C9 C10 C11 120.23(19) . . ? C9 C10 H10 119.9 . . ? C7' C8' H8' 120.0 . . ? C7' C8' C9' 120.08(18) . . ? C9' C8' H8' 120.0 . . ? C6' C7' H7' 119.5 . . ? C8' C7' C6' 121.07(17) . . ? C8' C7' H7' 119.5 . . ? C6' C5' H5' 115.0 . . ? C4' C5' C6' 129.93(16) . . ? C4' C5' H5' 115.0 . . ? C6' C11' H11' 119.8 . . ? C10' C11' C6' 120.45(17) . . ? C10' C11' H11' 119.8 . . ? C5' C4' C3' 121.94(16) . . ? C5' C4' C12' 136.32(16) . . ? C12' C4' C3' 101.69(14) . . ? O1' C3' C4' 118.24(15) . . ? N1' C3' O1' 125.91(16) . . ? N1' C3' C4' 115.80(16) . . ? O1' C2' H2'A 109.8 . . ? O1' C2' H2'B 109.8 . . ? O1' C2' C1' 109.52(18) . . ? H2'A C2' H2'B 108.2 . . ? C1' C2' H2'A 109.8 . . ? C1' C2' H2'B 109.8 . . ? C14' C13' H13' 120.6 . . ? C12' C13' H13' 120.6 . . ? C12' C13' C14' 118.74(17) . . ? C13' C14' H14' 119.4 . . ? C15' C14' C13' 121.14(19) . . ? C15' C14' H14' 119.4 . . ? C17' C16' H16' 121.1 . . ? C15' C16' H16' 121.1 . . ? C15' C16' C17' 117.71(18) . . ? F1' C1' F2' 106.0(2) . . ? F1' C1' F3' 107.40(19) . . ? F1' C1' C2' 114.35(19) . . ? F2' C1' C2' 111.53(19) . . ? F3' C1' F2' 107.12(19) . . ? F3' C1' C2' 110.1(2) . . ? C16' C17' N1' 125.79(17) . . ? C16' C17' C12' 121.40(18) . . ? C12' C17' N1' 112.78(16) . . ? C8' C9' H9' 120.2 . . ? C10' C9' C8' 119.69(17) . . ? C10' C9' H9' 120.2 . . ? C11' C10' H10' 119.7 . . ? C9' C10' C11' 120.51(17) . . ? C9' C10' H10' 119.7 . . ? C13' C12' C4' 135.25(16) . . ? C13' C12' C17' 119.64(17) . . ? C17' C12' C4' 104.96(15) . . ? C14' C15' C16' 121.33(19) . . ? C14' C15' H15' 119.3 . . ? C16' C15' H15' 119.3 . . ? C7 C6 C5 118.10(16) . . ? C11 C6 C7 117.95(16) . . ? C11 C6 C5 123.87(16) . . ? 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 F2 C1 1.328(2) . ? F1' C1' 1.308(3) . ? F3 C1 1.340(3) . ? F2' C1' 1.339(3) . ? F3' C1' 1.331(2) . ? F1 C1 1.309(3) . ? O1' C3' 1.349(2) . ? O1' C2' 1.419(2) . ? O1 C3 1.351(2) . ? O1 C2 1.419(2) . ? N1' H1' 0.8600 . ? N1' C3' 1.280(2) . ? N1' C17' 1.416(2) . ? N1 H1 0.8600 . ? N1 C3 1.279(2) . ? N1 C17 1.415(2) . ? C8 H8 0.9300 . ? C8 C7 1.374(2) . ? C8 C9 1.382(3) . ? C7 H7 0.9300 . ? C7 C6 1.400(2) . ? C5 H5 0.9300 . ? C5 C4 1.348(2) . ? C5 C6 1.461(2) . ? C11 H11 0.9300 . ? C11 C10 1.383(3) . ? C11 C6 1.395(2) . ? C4 C12 1.469(2) . ? C4 C3 1.473(2) . ? C12 C13 1.386(2) . ? C12 C17 1.410(2) . ? C13 H13 0.9300 . ? C13 C14 1.391(3) . ? C1 C2 1.482(3) . ? C6' C7' 1.395(2) . ? C6' C5' 1.465(2) . ? C6' C11' 1.395(2) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C16 H16 0.9300 . ? C16 C15 1.388(3) . ? C16 C17 1.387(3) . ? C15 H15 0.9300 . ? C15 C14 1.377(3) . ? C14 H14 0.9300 . ? C9 H9 0.9300 . ? C9 C10 1.380(3) . ? C10 H10 0.9300 . ? C8' H8' 0.9300 . ? C8' C7' 1.380(2) . ? C8' C9' 1.381(3) . ? C7' H7' 0.9300 . ? C5' H5' 0.9300 . ? C5' C4' 1.344(2) . ? C11' H11' 0.9300 . ? C11' C10' 1.384(2) . ? C4' C3' 1.480(2) . ? C4' C12' 1.472(2) . ? C2' H2'A 0.9700 . ? C2' H2'B 0.9700 . ? C2' C1' 1.482(3) . ? C13' H13' 0.9300 . ? C13' C14' 1.394(3) . ? C13' C12' 1.386(2) . ? C14' H14' 0.9300 . ? C14' C15' 1.379(3) . ? C16' H16' 0.9300 . ? C16' C17' 1.394(3) . ? C16' C15' 1.388(3) . ? C17' C12' 1.410(2) . ? C9' H9' 0.9300 . ? C9' C10' 1.380(3) . ? C10' H10' 0.9300 . ? C15' H15' 0.9300 . ? 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 F2 C1 C2 O1 -176.07(17) . . . . ? F3 C1 C2 O1 64.0(2) . . . . ? F1 C1 C2 O1 -55.5(3) . . . . ? O1' C2' C1' F1' 54.1(3) . . . . ? O1' C2' C1' F2' -66.1(2) . . . . ? O1' C2' C1' F3' 175.09(17) . . . . ? N1' C17' C12' C4' 1.5(2) . . . . ? N1' C17' C12' C13' 177.72(16) . . . . ? C8 C7 C6 C5 -179.49(18) . . . . ? C8 C7 C6 C11 -2.7(3) . . . . ? C8 C9 C10 C11 -1.1(4) . . . . ? C7 C8 C9 C10 0.1(4) . . . . ? C5 C4 C12 C13 6.9(4) . . . . ? C5 C4 C12 C17 179.5(2) . . . . ? C5 C4 C3 O1 -1.4(3) . . . . ? C5 C4 C3 N1 178.77(17) . . . . ? C4 C5 C6 C7 -153.90(19) . . . . ? C4 C5 C6 C11 29.5(3) . . . . ? C4 C12 C13 C14 174.2(2) . . . . ? C4 C12 C17 N1 -1.0(2) . . . . ? C4 C12 C17 C16 -178.43(18) . . . . ? C12 C4 C3 O1 176.24(16) . . . . ? C12 C4 C3 N1 -3.6(2) . . . . ? C12 C13 C14 C15 0.7(3) . . . . ? C13 C12 C17 N1 173.06(17) . . . . ? C13 C12 C17 C16 -4.4(3) . . . . ? C6' C5' C4' C3' -175.72(18) . . . . ? C6' C5' C4' C12' 7.6(4) . . . . ? C6' C11' C10' C9' 0.1(3) . . . . ? C3 O1 C2 C1 -109.2(2) . . . . ? C3 N1 C17 C12 -1.2(2) . . . . ? C3 N1 C17 C16 176.1(2) . . . . ? C3 C4 C12 C13 -170.2(2) . . . . ? C3 C4 C12 C17 2.40(18) . . . . ? C2 O1 C3 N1 12.0(3) . . . . ? C2 O1 C3 C4 -167.79(17) . . . . ? C16 C15 C14 C13 -2.0(4) . . . . ? C15 C16 C17 N1 -174.0(2) . . . . ? C15 C16 C17 C12 3.1(3) . . . . ? C17 N1 C3 O1 -176.78(18) . . . . ? C17 N1 C3 C4 3.0(2) . . . . ? C17 C12 C13 C14 2.4(3) . . . . ? C17 C16 C15 C14 0.0(4) . . . . ? C9 C8 C7 C6 1.8(3) . . . . ? C10 C11 C6 C7 1.7(3) . . . . ? C10 C11 C6 C5 178.32(18) . . . . ? C8' C9' C10' C11' -1.4(3) . . . . ? C7' C6' C5' C4' -145.1(2) . . . . ? C7' C6' C11' C10' 1.8(3) . . . . ? C7' C8' C9' C10' 0.7(3) . . . . ? C5' C6' C7' C8' -179.12(17) . . . . ? C5' C6' C11' C10' 178.32(17) . . . . ? C5' C4' C3' O1' 4.8(3) . . . . ? C5' C4' C3' N1' -177.52(18) . . . . ? C5' C4' C12' C13' 0.9(4) . . . . ? C5' C4' C12' C17' 176.2(2) . . . . ? C11' C6' C7' C8' -2.5(3) . . . . ? C11' C6' C5' C4' 38.5(3) . . . . ? C3' O1' C2' C1' 111.0(2) . . . . ? C3' N1' C17' C16' 176.63(19) . . . . ? C3' N1' C17' C12' -1.4(2) . . . . ? C3' C4' C12' C13' -176.3(2) . . . . ? C3' C4' C12' C17' -0.96(18) . . . . ? C2' O1' C3' N1' -7.6(3) . . . . ? C2' O1' C3' C4' 169.83(17) . . . . ? C13' C14' C15' C16' -1.2(3) . . . . ? C14' C13' C12' C4' 176.06(19) . . . . ? C14' C13' C12' C17' 1.2(3) . . . . ? C16' C17' C12' C4' -176.62(17) . . . . ? C16' C17' C12' C13' -0.4(3) . . . . ? C17' N1' C3' O1' 178.20(19) . . . . ? C17' N1' C3' C4' 0.7(2) . . . . ? C17' C16' C15' C14' 2.0(3) . . . . ? C9' C8' C7' C6' 1.2(3) . . . . ? C12' C4' C3' O1' -177.54(17) . . . . ? C12' C4' C3' N1' 0.2(2) . . . . ? C12' C13' C14' C15' -0.5(3) . . . . ? C15' C16' C17' N1' -179.04(19) . . . . ? C15' C16' C17' C12' -1.2(3) . . . . ? C6 C5 C4 C12 8.3(4) . . . . ? C6 C5 C4 C3 -174.99(17) . . . . ? C6 C11 C10 C9 0.2(3) . . . . ?