#------------------------------------------------------------------------------ #$Date: 2024-02-04 14:16:44 +0200 (Sun, 04 Feb 2024) $ #$Revision: 289565 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/77/7247784.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_7247784 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 thio-oxindoles ; _journal_issue 1 _journal_name_full 'Green Chemistry' _journal_page_first 448 _journal_page_last 455 _journal_paper_doi 10.1039/D3GC03702A _journal_volume 26 _journal_year 2024 _chemical_formula_moiety 'C22 H16 F3 N O' _chemical_formula_sum 'C22 H16 F3 N O' _chemical_formula_weight 367.36 _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _atom_sites_solution_hydrogens difmap _audit_creation_date 2023-02-21 _audit_creation_method ; Olex2 1.5 (compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498) ; _audit_update_record ; 2023-02-21 deposited with the CCDC. 2023-11-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.8883(9) _cell_length_b 15.522(2) _cell_length_c 16.668(2) _cell_measurement_reflns_used 4477 _cell_measurement_temperature 298 _cell_measurement_theta_max 24.97 _cell_measurement_theta_min 2.77 _cell_volume 1782.1(4) _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 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _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 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device 'three-circle diffractometer' _diffrn_measurement_device_type 'Bruker SMART APEX2 area detector' _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 0.0469 _diffrn_reflns_av_unetI/netI 0.0457 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.996 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 11776 _diffrn_reflns_point_group_measured_fraction_full 0.967 _diffrn_reflns_point_group_measured_fraction_max 0.962 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.406 _diffrn_reflns_theta_min 2.774 _diffrn_source 'microfocus sealed X-ray tube' _diffrn_source_type 'Incoatec I\ms' _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.5914 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1251 before and 0.0637 after correction. The Ratio of minimum to maximum transmission is 0.7916. The \l/2 correction factor is Not present. ; _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.369 _exptl_crystal_description plate _exptl_crystal_F_000 760 _exptl_crystal_size_max 0.356 _exptl_crystal_size_mid 0.256 _exptl_crystal_size_min 0.098 _refine_diff_density_max 0.109 _refine_diff_density_min -0.118 _refine_diff_density_rms 0.028 _refine_ls_abs_structure_details ; Flack x determined using 1136 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.4(5) _refine_ls_extinction_coef 0.021(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 309 _refine_ls_number_reflns 3526 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.034 _refine_ls_R_factor_all 0.0521 _refine_ls_R_factor_gt 0.0387 _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^)+(0.0413P)^2^+0.1624P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.0965 _reflns_Friedel_coverage 0.860 _reflns_Friedel_fraction_full 0.936 _reflns_Friedel_fraction_max 0.925 _reflns_number_gt 2903 _reflns_number_total 3526 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3gc03702a2.cif _cod_data_source_block agml_661_0m _cod_depositor_comments 'Adding full bibliography for 7247784--7247789.cif.' _cod_database_code 7247784 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; ; _shelx_res_file ; TITL agml_661_0m_a.res in Pca2(1) agml_661_0m.res created by SHELXL-2018/3 at 11:44:45 on 21-Feb-2023 REM Old TITL AGML_661_0m in Pca2(1) REM SHELXT solution in Pca2(1): R1 0.127, Rweak 0.021, Alpha 0.001 REM 0.827 for 231 systematic absences, Orientation as input REM Flack x = 0.439 ( 0.411 ) from 1207 Parsons' quotients REM Formula found by SHELXT: C22 N O F3 CELL 0.71073 6.8883 15.5217 16.6678 90 90 90 ZERR 4 0.0009 0.0024 0.0024 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,-Y,+Z SYMM 0.5-X,+Y,0.5+Z SFAC C H F N O UNIT 88 64 12 4 4 L.S. 4 PLAN 5 0 0 TEMP 24.85 CONF list 4 MORE -1 BOND $H fmap 2 acta REM REM REM WGHT 0.041300 0.162400 EXTI 0.020690 FVAR 1.01352 O1 5 0.286379 0.698234 0.536507 11.00000 0.04541 0.06642 = 0.04190 -0.00097 0.00369 -0.01091 N1 4 0.491562 0.784582 0.612523 11.00000 0.04862 0.05982 = 0.03772 -0.00588 0.00474 -0.00281 F3 3 0.127345 0.545910 0.607305 11.00000 0.14937 0.06580 = 0.09560 -0.01315 -0.00321 -0.03133 F2 3 0.340961 0.604490 0.677305 11.00000 0.12225 0.10334 = 0.13084 0.04058 -0.05957 -0.00939 F1 3 0.045288 0.617103 0.708742 11.00000 0.19522 0.11192 = 0.09812 0.01423 0.08405 -0.01832 C17 1 0.717482 0.824452 0.514452 11.00000 0.04218 0.04473 = 0.03934 -0.00153 -0.00258 0.00198 C11 1 0.441820 0.813487 0.410065 11.00000 0.03967 0.04830 = 0.03435 -0.00252 0.00263 0.00286 C5 1 0.669266 0.687903 0.437905 11.00000 0.03617 0.05006 = 0.04426 -0.00575 -0.00152 -0.00080 C16 1 0.450756 0.901436 0.397862 11.00000 0.05233 0.05309 = 0.05198 -0.00063 -0.00220 -0.00125 C6 1 0.707135 0.615777 0.483532 11.00000 0.05103 0.05443 = 0.05564 -0.00344 -0.00366 0.00064 C3 1 0.444135 0.748655 0.546754 11.00000 0.03980 0.05088 = 0.03895 0.00260 0.00189 0.00068 C4 1 0.568231 0.767507 0.472620 11.00000 0.04299 0.04749 = 0.03476 -0.00283 0.00354 -0.00136 C12 1 0.311057 0.765393 0.363759 11.00000 0.05143 0.05587 = 0.04434 -0.00695 0.00039 -0.00274 C22 1 0.664247 0.831530 0.594811 11.00000 0.04509 0.05109 = 0.03987 -0.00433 0.00134 0.00229 C18 1 0.885692 0.862793 0.487410 11.00000 0.04627 0.05817 = 0.04705 0.00231 0.00074 -0.00289 C13 1 0.200654 0.805306 0.305165 11.00000 0.04652 0.07712 = 0.04119 -0.00472 -0.00348 0.00017 C15 1 0.337685 0.940714 0.339436 11.00000 0.06164 0.05805 = 0.06763 0.01243 -0.00193 0.00727 C1 1 0.165518 0.615781 0.647984 11.00000 0.07151 0.06397 = 0.05029 -0.00397 0.00198 -0.01282 C14 1 0.215371 0.892244 0.292929 11.00000 0.05070 0.08466 = 0.04703 0.01134 -0.00112 0.01244 C20 1 0.942745 0.918061 0.620380 11.00000 0.05625 0.06023 = 0.06521 -0.01020 -0.01565 -0.00626 C19 1 0.997654 0.910409 0.540971 11.00000 0.04634 0.05665 = 0.06754 0.00417 -0.00713 -0.00547 C21 1 0.775206 0.877478 0.648627 11.00000 0.05964 0.06476 = 0.04347 -0.01365 -0.00500 0.00148 C2 1 0.148537 0.696492 0.601650 11.00000 0.04234 0.06749 = 0.05712 0.00456 0.01103 -0.00297 C10 1 0.736773 0.689746 0.359321 11.00000 0.06344 0.07182 = 0.05099 -0.00190 0.01257 0.01043 C8 1 0.876424 0.549078 0.375072 11.00000 0.05198 0.07311 = 0.09016 -0.02957 -0.00350 0.01211 C7 1 0.809846 0.546785 0.452678 11.00000 0.06199 0.05793 = 0.08342 -0.00741 -0.00619 0.01060 C9 1 0.838680 0.620193 0.328186 11.00000 0.06279 0.09799 = 0.06623 -0.02571 0.01690 0.00780 H18 2 0.929580 0.858002 0.432819 11.00000 0.05937 H21 2 0.734199 0.880679 0.707408 11.00000 0.06148 H20 2 1.024978 0.951728 0.658386 11.00000 0.06767 H19 2 1.126823 0.942505 0.522903 11.00000 0.07400 H2A 2 0.184059 0.747967 0.637558 11.00000 0.06850 H12 2 0.301158 0.701924 0.372592 11.00000 0.04625 H16 2 0.530526 0.935776 0.428034 11.00000 0.05410 H10 2 0.705255 0.737694 0.326587 11.00000 0.07062 H15 2 0.343562 0.999473 0.332546 11.00000 0.07793 H7 2 0.836465 0.494472 0.485122 11.00000 0.10612 H13 2 0.107342 0.772756 0.269062 11.00000 0.06802 H9 2 0.879933 0.621181 0.274031 11.00000 0.07730 H6 2 0.659840 0.613810 0.539051 11.00000 0.06847 H8 2 0.947862 0.497895 0.352485 11.00000 0.09161 H2B 2 0.016751 0.695567 0.577003 11.00000 0.08484 H14 2 0.137754 0.921114 0.253068 11.00000 0.07588 HKLF 4 REM agml_661_0m_a.res in Pca2(1) REM wR2 = 0.0965, GooF = S = 1.035, Restrained GooF = 1.034 for all data REM R1 = 0.0387 for 2903 Fo > 4sig(Fo) and 0.0521 for all 3526 data REM 309 parameters refined using 1 restraints END WGHT 0.0413 0.1624 REM Highest difference peak 0.109, deepest hole -0.118, 1-sigma level 0.028 Q1 1 0.0448 0.6101 0.7273 11.00000 0.05 0.11 Q2 1 0.1975 0.8164 0.6383 11.00000 0.05 0.11 Q3 1 0.5616 0.5929 0.3980 11.00000 0.05 0.10 Q4 1 0.6201 0.6604 0.5850 11.00000 0.05 0.10 Q5 1 0.6028 0.7792 0.3162 11.00000 0.05 0.10 ; _shelx_res_checksum 42971 _olex2_submission_special_instructions 'No special instructions were received' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, 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 O1 O 0.2864(3) 0.69823(13) 0.53651(12) 0.0512(5) Uani 1 1 d . . . . . N1 N 0.4916(4) 0.78458(17) 0.61252(14) 0.0487(6) Uani 1 1 d . . . . . F3 F 0.1273(5) 0.54591(14) 0.60730(18) 0.1036(9) Uani 1 1 d . . . . . F2 F 0.3410(5) 0.60449(19) 0.6773(2) 0.1188(11) Uani 1 1 d . . . . . F1 F 0.0453(6) 0.6171(2) 0.70874(19) 0.1351(14) Uani 1 1 d . . . . . C17 C 0.7175(4) 0.82445(17) 0.51445(17) 0.0421(7) Uani 1 1 d . . . . . C11 C 0.4418(4) 0.81349(17) 0.41007(16) 0.0408(6) Uani 1 1 d . . . . . C5 C 0.6693(4) 0.68790(18) 0.43791(18) 0.0435(7) Uani 1 1 d . . . . . C16 C 0.4508(5) 0.9014(2) 0.3979(2) 0.0525(8) Uani 1 1 d . . . . . C6 C 0.7071(5) 0.6158(2) 0.4835(2) 0.0537(8) Uani 1 1 d . . . . . C3 C 0.4441(4) 0.74866(17) 0.54675(18) 0.0432(6) Uani 1 1 d . . . . . C4 C 0.5682(4) 0.76751(17) 0.47262(16) 0.0417(6) Uani 1 1 d . . . . . C12 C 0.3111(4) 0.7654(2) 0.36376(19) 0.0505(7) Uani 1 1 d . . . . . C22 C 0.6642(4) 0.83153(18) 0.59481(18) 0.0453(7) Uani 1 1 d . . . . . C18 C 0.8857(5) 0.8628(2) 0.4874(2) 0.0505(7) Uani 1 1 d . . . . . C13 C 0.2007(5) 0.8053(2) 0.30517(19) 0.0549(8) Uani 1 1 d . . . . . C15 C 0.3377(5) 0.9407(3) 0.3394(2) 0.0624(9) Uani 1 1 d . . . . . C1 C 0.1655(6) 0.6158(2) 0.6480(2) 0.0619(9) Uani 1 1 d . . . . . C14 C 0.2154(5) 0.8922(2) 0.2929(2) 0.0608(9) Uani 1 1 d . . . . . C20 C 0.9427(5) 0.9181(2) 0.6204(2) 0.0606(9) Uani 1 1 d . . . . . C19 C 0.9977(5) 0.9104(2) 0.5410(2) 0.0568(8) Uani 1 1 d . . . . . C21 C 0.7752(5) 0.8775(2) 0.6486(2) 0.0560(8) Uani 1 1 d . . . . . C2 C 0.1485(5) 0.6965(2) 0.6016(2) 0.0557(8) Uani 1 1 d . . . . . C10 C 0.7368(6) 0.6897(3) 0.3593(2) 0.0621(9) Uani 1 1 d . . . . . C8 C 0.8764(5) 0.5491(3) 0.3751(3) 0.0717(11) Uani 1 1 d . . . . . C7 C 0.8098(6) 0.5468(2) 0.4527(3) 0.0678(10) Uani 1 1 d . . . . . C9 C 0.8387(6) 0.6202(3) 0.3282(3) 0.0757(12) Uani 1 1 d . . . . . H18 H 0.930(5) 0.858(2) 0.433(2) 0.059(9) Uiso 1 1 d . . . . . H21 H 0.734(5) 0.881(2) 0.707(3) 0.061(9) Uiso 1 1 d . . . . . H20 H 1.025(5) 0.952(2) 0.658(2) 0.068(10) Uiso 1 1 d . . . . . H19 H 1.127(5) 0.943(2) 0.523(2) 0.074(11) Uiso 1 1 d . . . . . H2A H 0.184(5) 0.748(2) 0.638(2) 0.068(11) Uiso 1 1 d . . . . . H12 H 0.301(4) 0.702(2) 0.3726(19) 0.046(8) Uiso 1 1 d . . . . . H16 H 0.531(5) 0.936(2) 0.428(2) 0.054(9) Uiso 1 1 d . . . . . H10 H 0.705(5) 0.738(2) 0.327(2) 0.071(11) Uiso 1 1 d . . . . . H15 H 0.344(6) 0.999(3) 0.333(3) 0.078(12) Uiso 1 1 d . . . . . H7 H 0.836(7) 0.494(4) 0.485(3) 0.106(15) Uiso 1 1 d . . . . . H13 H 0.107(6) 0.773(2) 0.269(2) 0.068(10) Uiso 1 1 d . . . . . H9 H 0.880(6) 0.621(2) 0.274(3) 0.077(12) Uiso 1 1 d . . . . . H6 H 0.660(5) 0.614(2) 0.539(3) 0.068(11) Uiso 1 1 d . . . . . H8 H 0.948(6) 0.498(3) 0.352(3) 0.092(13) Uiso 1 1 d . . . . . H2B H 0.017(6) 0.696(3) 0.577(2) 0.085(13) Uiso 1 1 d . . . . . H14 H 0.138(6) 0.921(3) 0.253(3) 0.076(12) Uiso 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 O1 0.0454(12) 0.0664(12) 0.0419(11) -0.0010(10) 0.0037(10) -0.0109(9) N1 0.0486(14) 0.0598(14) 0.0377(12) -0.0059(12) 0.0047(12) -0.0028(11) F3 0.149(2) 0.0658(13) 0.0956(17) -0.0131(14) -0.0032(17) -0.0313(15) F2 0.122(3) 0.1033(19) 0.131(3) 0.0406(18) -0.060(2) -0.0094(16) F1 0.195(4) 0.112(2) 0.098(2) 0.0142(17) 0.084(2) -0.018(2) C17 0.0422(15) 0.0447(15) 0.0393(14) -0.0015(12) -0.0026(13) 0.0020(12) C11 0.0397(14) 0.0483(14) 0.0344(14) -0.0025(12) 0.0026(12) 0.0029(12) C5 0.0362(14) 0.0501(15) 0.0443(16) -0.0057(13) -0.0015(13) -0.0008(12) C16 0.0523(18) 0.0531(17) 0.0520(19) -0.0006(15) -0.0022(16) -0.0013(14) C6 0.0510(18) 0.0544(17) 0.056(2) -0.0034(15) -0.0037(17) 0.0006(15) C3 0.0398(15) 0.0509(14) 0.0390(14) 0.0026(13) 0.0019(13) 0.0007(12) C4 0.0430(15) 0.0475(14) 0.0348(14) -0.0028(12) 0.0035(13) -0.0014(12) C12 0.0514(18) 0.0559(18) 0.0443(16) -0.0070(14) 0.0004(15) -0.0027(14) C22 0.0451(16) 0.0511(15) 0.0399(15) -0.0043(13) 0.0013(13) 0.0023(12) C18 0.0463(17) 0.0582(17) 0.0471(18) 0.0023(14) 0.0007(15) -0.0029(14) C13 0.0465(19) 0.077(2) 0.0412(18) -0.0047(16) -0.0035(15) 0.0002(16) C15 0.062(2) 0.058(2) 0.068(2) 0.0124(17) -0.0019(18) 0.0073(17) C1 0.072(2) 0.064(2) 0.050(2) -0.0040(16) 0.0020(19) -0.0128(17) C14 0.051(2) 0.085(2) 0.0470(18) 0.0113(18) -0.0011(17) 0.0124(18) C20 0.056(2) 0.0602(19) 0.065(2) -0.0102(17) -0.0157(19) -0.0063(15) C19 0.0463(18) 0.0567(17) 0.068(2) 0.0042(17) -0.0071(18) -0.0055(14) C21 0.060(2) 0.0648(18) 0.0435(18) -0.0137(15) -0.0050(16) 0.0015(16) C2 0.0423(17) 0.067(2) 0.057(2) 0.0046(18) 0.0110(16) -0.0030(15) C10 0.063(2) 0.072(2) 0.0510(19) -0.0019(18) 0.0126(18) 0.0104(19) C8 0.052(2) 0.073(3) 0.090(3) -0.030(2) -0.004(2) 0.0121(18) C7 0.062(2) 0.0579(19) 0.083(3) -0.007(2) -0.006(2) 0.0106(17) C9 0.063(2) 0.098(3) 0.066(3) -0.026(2) 0.017(2) 0.008(2) 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 116.5(2) . . ? C3 N1 C22 105.1(2) . . ? C22 C17 C4 107.9(2) . . ? C18 C17 C4 131.9(3) . . ? C18 C17 C22 120.1(3) . . ? C16 C11 C4 122.3(3) . . ? C16 C11 C12 118.3(3) . . ? C12 C11 C4 119.4(2) . . ? C6 C5 C4 122.2(3) . . ? C6 C5 C10 118.2(3) . . ? C10 C5 C4 119.4(3) . . ? C11 C16 C15 120.8(3) . . ? C11 C16 H16 121(2) . . ? C15 C16 H16 118(2) . . ? C5 C6 C7 121.4(4) . . ? C5 C6 H6 119(2) . . ? C7 C6 H6 120(2) . . ? O1 C3 C4 117.3(2) . . ? N1 C3 O1 124.7(3) . . ? N1 C3 C4 117.9(2) . . ? C17 C4 C11 115.1(2) . . ? C17 C4 C5 109.5(2) . . ? C17 C4 C3 96.8(2) . . ? C5 C4 C11 112.1(2) . . ? C3 C4 C11 108.7(2) . . ? C3 C4 C5 113.9(2) . . ? C11 C12 H12 119.2(18) . . ? C13 C12 C11 120.2(3) . . ? C13 C12 H12 120.5(18) . . ? C17 C22 N1 112.2(2) . . ? C21 C22 N1 126.3(3) . . ? C21 C22 C17 121.4(3) . . ? C17 C18 C19 119.0(3) . . ? C17 C18 H18 123(2) . . ? C19 C18 H18 118(2) . . ? C12 C13 H13 123(2) . . ? C14 C13 C12 120.4(3) . . ? C14 C13 H13 117(2) . . ? C16 C15 H15 120(3) . . ? C14 C15 C16 120.1(4) . . ? C14 C15 H15 120(3) . . ? F3 C1 F2 105.5(3) . . ? F3 C1 F1 106.7(3) . . ? F3 C1 C2 114.7(3) . . ? F2 C1 C2 112.3(3) . . ? F1 C1 F2 107.2(4) . . ? F1 C1 C2 110.0(3) . . ? C13 C14 C15 120.2(3) . . ? C13 C14 H14 121(2) . . ? C15 C14 H14 118(2) . . ? C19 C20 C21 120.7(3) . . ? C19 C20 H20 120(2) . . ? C21 C20 H20 119(2) . . ? C18 C19 H19 122(2) . . ? C20 C19 C18 120.6(3) . . ? C20 C19 H19 117(2) . . ? C22 C21 C20 118.2(3) . . ? C22 C21 H21 120(2) . . ? C20 C21 H21 122(2) . . ? O1 C2 C1 110.9(3) . . ? O1 C2 H2A 105(2) . . ? O1 C2 H2B 107(2) . . ? C1 C2 H2A 110(2) . . ? C1 C2 H2B 106(2) . . ? H2A C2 H2B 118(3) . . ? C5 C10 H10 119(2) . . ? C9 C10 C5 120.4(4) . . ? C9 C10 H10 121(2) . . ? C7 C8 C9 119.5(4) . . ? C7 C8 H8 120(3) . . ? C9 C8 H8 121(3) . . ? C6 C7 H7 122(3) . . ? C8 C7 C6 120.1(4) . . ? C8 C7 H7 118(3) . . ? C10 C9 H9 120(2) . . ? C8 C9 C10 120.4(4) . . ? C8 C9 H9 120(2) . . ? 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 O1 C3 1.350(3) . ? O1 C2 1.443(4) . ? N1 C3 1.273(4) . ? N1 C22 1.426(4) . ? F3 C1 1.306(4) . ? F2 C1 1.315(4) . ? F1 C1 1.308(4) . ? C17 C4 1.525(4) . ? C17 C22 1.393(4) . ? C17 C18 1.378(4) . ? C11 C16 1.382(4) . ? C11 C4 1.534(4) . ? C11 C12 1.402(4) . ? C5 C6 1.378(5) . ? C5 C4 1.532(4) . ? C5 C10 1.390(5) . ? C16 C15 1.388(5) . ? C16 H16 0.92(3) . ? C6 C7 1.383(5) . ? C6 H6 0.98(4) . ? C3 C4 1.531(4) . ? C12 C13 1.384(5) . ? C12 H12 1.00(3) . ? C22 C21 1.377(4) . ? C18 C19 1.392(5) . ? C18 H18 0.96(4) . ? C13 C14 1.369(5) . ? C13 H13 1.02(4) . ? C15 C14 1.370(5) . ? C15 H15 0.92(4) . ? C1 C2 1.476(5) . ? C14 H14 0.96(4) . ? C20 C19 1.382(5) . ? C20 C21 1.397(5) . ? C20 H20 1.00(4) . ? C19 H19 1.06(4) . ? C21 H21 1.02(4) . ? C2 H2A 1.03(4) . ? C2 H2B 1.00(4) . ? C10 C9 1.388(5) . ? C10 H10 0.95(4) . ? C8 C7 1.373(6) . ? C8 C9 1.377(6) . ? C8 H8 1.01(5) . ? C7 H7 0.99(5) . ? C9 H9 0.95(5) . ? 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 O1 C3 C4 C17 179.5(2) . . . . ? O1 C3 C4 C11 60.1(3) . . . . ? O1 C3 C4 C5 -65.7(3) . . . . ? N1 C3 C4 C17 2.6(3) . . . . ? N1 C3 C4 C11 -116.8(3) . . . . ? N1 C3 C4 C5 117.5(3) . . . . ? N1 C22 C21 C20 178.6(3) . . . . ? F3 C1 C2 O1 -62.5(4) . . . . ? F2 C1 C2 O1 57.9(4) . . . . ? F1 C1 C2 O1 177.3(3) . . . . ? C17 C22 C21 C20 0.7(5) . . . . ? C17 C18 C19 C20 1.0(5) . . . . ? C11 C16 C15 C14 -0.1(5) . . . . ? C11 C12 C13 C14 -1.2(5) . . . . ? C5 C6 C7 C8 -0.1(5) . . . . ? C5 C10 C9 C8 -0.9(6) . . . . ? C16 C11 C4 C17 -5.6(4) . . . . ? C16 C11 C4 C5 -131.6(3) . . . . ? C16 C11 C4 C3 101.6(3) . . . . ? C16 C11 C12 C13 2.7(4) . . . . ? C16 C15 C14 C13 1.6(5) . . . . ? C6 C5 C4 C17 83.7(3) . . . . ? C6 C5 C4 C11 -147.3(3) . . . . ? C6 C5 C4 C3 -23.4(4) . . . . ? C6 C5 C10 C9 0.3(5) . . . . ? C3 O1 C2 C1 -104.0(3) . . . . ? C3 N1 C22 C17 1.6(3) . . . . ? C3 N1 C22 C21 -176.5(3) . . . . ? C4 C17 C22 N1 0.0(3) . . . . ? C4 C17 C22 C21 178.2(3) . . . . ? C4 C17 C18 C19 -178.3(3) . . . . ? C4 C11 C16 C15 178.5(3) . . . . ? C4 C11 C12 C13 -177.8(3) . . . . ? C4 C5 C6 C7 -175.7(3) . . . . ? C4 C5 C10 C9 176.2(3) . . . . ? C12 C11 C16 C15 -2.1(5) . . . . ? C12 C11 C4 C17 174.9(3) . . . . ? C12 C11 C4 C5 48.9(3) . . . . ? C12 C11 C4 C3 -77.9(3) . . . . ? C12 C13 C14 C15 -0.9(5) . . . . ? C22 N1 C3 O1 -179.3(3) . . . . ? C22 N1 C3 C4 -2.7(3) . . . . ? C22 C17 C4 C11 113.0(3) . . . . ? C22 C17 C4 C5 -119.6(3) . . . . ? C22 C17 C4 C3 -1.3(3) . . . . ? C22 C17 C18 C19 -1.8(4) . . . . ? C18 C17 C4 C11 -70.2(4) . . . . ? C18 C17 C4 C5 57.2(4) . . . . ? C18 C17 C4 C3 175.5(3) . . . . ? C18 C17 C22 N1 -177.2(3) . . . . ? C18 C17 C22 C21 0.9(4) . . . . ? C19 C20 C21 C22 -1.5(5) . . . . ? C21 C20 C19 C18 0.7(5) . . . . ? C2 O1 C3 N1 9.9(4) . . . . ? C2 O1 C3 C4 -166.7(2) . . . . ? C10 C5 C6 C7 0.2(5) . . . . ? C10 C5 C4 C17 -92.0(3) . . . . ? C10 C5 C4 C11 37.0(4) . . . . ? C10 C5 C4 C3 160.9(3) . . . . ? C7 C8 C9 C10 1.0(6) . . . . ? C9 C8 C7 C6 -0.5(6) . . . . ?