#------------------------------------------------------------------------------ #$Date: 2019-04-10 04:06:12 +0300 (Wed, 10 Apr 2019) $ #$Revision: 214578 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/67/7156777.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_7156777 loop_ _publ_author_name 'Guo, Jia' 'Xu, Cong' 'Wang, Ling' 'Huang, Wanqiao' 'Wang, Mang' _publ_section_title ; Catalyst-Free and Selective Trifluoromethylative Cyclizations of Acryloanilides Using PhICF3Cl ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/C9OB00601J _journal_year 2019 _chemical_formula_moiety '0.21(C20 H18 F3 N O)' _chemical_formula_sum 'C4.21 H3.79 F0.63 N0.21 O0.21' _chemical_formula_weight 72.71 _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' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_block_doi 10.5517/ccdc.csd.cc207z9k _audit_creation_date 2018-05-13 _audit_creation_method ; Olex2 1.2 (compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335) ; _audit_update_record ; 2018-07-09 deposited with the CCDC. 2019-04-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.736(6) _cell_angle_gamma 90 _cell_formula_units_Z 19 _cell_length_a 8.1844(9) _cell_length_b 24.475(3) _cell_length_c 8.6835(9) _cell_measurement_reflns_used 6162 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 72.11 _cell_measurement_theta_min 3.61 _cell_volume 1665.7(3) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 294.21 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.988 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0302 _diffrn_reflns_av_unetI/netI 0.0267 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.988 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 12352 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.988 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 72.302 _diffrn_reflns_theta_min 3.612 _exptl_absorpt_coefficient_mu 0.908 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.377 _exptl_crystal_description block _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.226 _refine_diff_density_min -0.256 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 298 _refine_ls_number_reflns 3252 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.050 _refine_ls_R_factor_all 0.0664 _refine_ls_R_factor_gt 0.0520 _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^)+(0.0502P)^2^+0.7873P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1199 _refine_ls_wR_factor_ref 0.1280 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2586 _reflns_number_total 3252 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9ob00601j2.cif _cod_data_source_block a _cod_database_code 7156777 _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. ; _olex2_refinement_description ; ; _shelx_res_file ; a.res created by SHELXL-2014/7 TITL a_a.res in P2(1)/n REM Old TITL a in P2(1)/n REM SHELXT solution in P2(1)/n REM R1 0.197, Rweak 0.021, Alpha 0.048, Orientation as input REM Formula found by SHELXT: C19 N2 O F3 CELL 1.54178 8.1844 24.4751 8.6835 90 106.736 90 ZERR 19 0.0009 0.0029 0.0009 0 0.006 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H F N O UNIT 80 72 12 4 4 L.S. 10 PLAN 20 TEMP 21.06 BOND $H LIST 6 fmap 2 acta REM REM REM WGHT 0.050200 0.787300 FVAR 1.01586 F1 3 1.011111 0.551762 0.905582 11.00000 0.06582 0.12173 = 0.06064 0.02230 0.00467 0.01184 O1 5 0.765665 0.623398 1.072742 11.00000 0.08745 0.07095 = 0.03790 0.00592 0.02611 -0.00504 F3 3 1.120915 0.601063 0.766742 11.00000 0.04346 0.10543 = 0.12344 0.02858 0.00476 -0.00730 N1 4 0.863966 0.680672 0.916965 11.00000 0.05688 0.04322 = 0.03097 -0.00630 0.01090 -0.00681 F2 3 1.111420 0.515038 0.731623 11.00000 0.09355 0.12179 = 0.13291 -0.02489 0.00157 0.07304 C15 1 0.815259 0.664446 0.629305 11.00000 0.03251 0.03453 = 0.03254 -0.00223 0.00974 0.00013 C16 1 0.872208 0.698306 0.764296 11.00000 0.03985 0.03732 = 0.03581 -0.00323 0.01118 -0.00423 C10 1 0.734077 0.608896 0.640752 11.00000 0.03643 0.02937 = 0.03175 -0.00219 0.00868 0.00059 C5 1 0.568543 0.604919 0.501504 11.00000 0.04227 0.02932 = 0.04018 -0.00110 0.00493 -0.00355 C20 1 0.834166 0.682904 0.484237 11.00000 0.05293 0.04691 = 0.03720 -0.00465 0.01864 -0.00640 C13 1 0.769842 0.636920 0.938477 11.00000 0.04979 0.04353 = 0.03392 0.00241 0.01565 0.00565 C11 1 0.854019 0.561305 0.630434 11.00000 0.04980 0.04082 = 0.04677 -0.00331 0.01443 0.00844 C8 1 0.660405 0.608596 0.788458 11.00000 0.04045 0.03476 = 0.04041 0.00363 0.01606 -0.00002 C6 1 0.432360 0.624639 0.550651 11.00000 0.03944 0.03626 = 0.05536 0.00392 0.00849 -0.00184 C7 1 0.492969 0.641987 0.722897 11.00000 0.04072 0.04634 = 0.05452 0.00188 0.02074 0.00333 C9 1 0.614102 0.551422 0.832437 11.00000 0.06213 0.04178 = 0.06318 0.00873 0.02310 -0.00684 C4 1 0.543937 0.586642 0.345117 11.00000 0.06086 0.03819 = 0.04538 -0.00788 0.00364 -0.00315 C17 1 0.941494 0.749353 0.748997 11.00000 0.06159 0.04640 = 0.05199 -0.01262 0.01812 -0.01773 C19 1 0.905551 0.733082 0.471216 11.00000 0.07864 0.05656 = 0.05046 0.00577 0.03309 -0.01387 C18 1 0.957815 0.766390 0.603272 11.00000 0.07749 0.04653 = 0.06663 -0.00097 0.03142 -0.02257 C12 1 1.021785 0.557348 0.756666 11.00000 0.04715 0.05910 = 0.06455 0.00460 0.01525 0.01529 C2 1 0.268945 0.625722 0.443343 11.00000 0.04201 0.05806 = 0.07807 0.00890 0.00311 0.00188 C3 1 0.379838 0.587963 0.238887 11.00000 0.07862 0.04794 = 0.04928 -0.00529 -0.01085 -0.00657 C1 1 0.244750 0.606661 0.288259 11.00000 0.05850 0.05861 = 0.07584 0.00486 -0.02032 -0.00841 C14 1 0.951782 0.712788 1.058920 11.00000 0.09680 0.06092 = 0.03657 -0.01186 0.00718 -0.01277 H9A 2 0.541585 0.533076 0.735866 11.00000 0.06241 H9B 2 0.548288 0.554339 0.912335 11.00000 0.09510 H9C 2 0.715015 0.527898 0.875167 11.00000 0.06609 H14A 2 0.947634 0.690535 1.152533 11.00000 0.08333 H14B 2 1.075031 0.717397 1.061304 11.00000 0.08604 H14C 2 0.893308 0.748639 1.057139 11.00000 0.09069 H7A 2 0.521588 0.684129 0.730889 11.00000 0.05079 H7B 2 0.419306 0.634637 0.784841 11.00000 0.06065 H20 2 0.794147 0.659839 0.389279 11.00000 0.05688 H4 2 0.643717 0.571686 0.308255 11.00000 0.05884 H17 2 0.974769 0.773107 0.840104 11.00000 0.06599 H1 2 0.129878 0.605622 0.210517 11.00000 0.09196 H3 2 0.358463 0.573098 0.124183 11.00000 0.07994 H19 2 0.914256 0.744532 0.371544 11.00000 0.08125 H2 2 0.175918 0.637560 0.482805 11.00000 0.07352 H18 2 1.005700 0.802154 0.593571 11.00000 0.07797 H11A 2 0.881606 0.564822 0.531240 11.00000 0.05016 H11B 2 0.795202 0.525232 0.627245 11.00000 0.06237 HKLF 4 REM a_a.res in P2(1)/n REM R1 = 0.0520 for 2586 Fo > 4sig(Fo) and 0.0664 for all 3252 data REM 298 parameters refined using 0 restraints END WGHT 0.0502 0.7873 REM Highest difference peak 0.226, deepest hole -0.256, 1-sigma level 0.037 Q1 1 0.7088 0.6089 0.7253 11.00000 0.05 0.23 Q2 1 1.0291 0.5165 0.8391 11.00000 0.05 0.22 Q3 1 0.5770 0.6229 0.7554 11.00000 0.05 0.21 Q4 1 0.6561 0.6069 0.5605 11.00000 0.05 0.20 Q5 1 1.1222 0.5681 0.6807 11.00000 0.05 0.19 Q6 1 1.0356 0.5852 0.8572 11.00000 0.05 0.18 Q7 1 0.7147 0.6223 0.8574 11.00000 0.05 0.17 Q8 1 0.4976 0.6097 0.5366 11.00000 0.05 0.15 Q9 1 0.6303 0.5831 0.8078 11.00000 0.05 0.14 Q10 1 0.8043 0.5894 0.6459 11.00000 0.05 0.14 Q11 1 0.5334 0.5779 0.4465 11.00000 0.05 0.13 Q12 1 0.8310 0.6097 1.0221 11.00000 0.05 0.13 Q13 1 0.8410 0.6910 0.8357 11.00000 0.05 0.13 Q14 1 0.4459 0.6393 0.6205 11.00000 0.05 0.12 Q15 1 0.7844 0.6342 0.6396 11.00000 0.05 0.12 Q16 1 0.5634 0.6036 0.4405 11.00000 0.05 0.12 Q17 1 0.8388 0.5348 0.5289 11.00000 0.05 0.12 Q18 1 0.8553 0.6770 0.7023 11.00000 0.05 0.12 Q19 1 0.3953 0.6481 0.4920 11.00000 0.05 0.11 Q20 1 1.2123 0.4675 0.7413 11.00000 0.05 0.11 ; _shelx_res_checksum 3034 _olex2_submission_special_instructions 'No special instructions were received' 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 F1 F 1.0111(2) 0.55176(8) 0.90558(18) 0.0856(5) Uani 1 1 d O1 O 0.7657(2) 0.62340(7) 1.07274(18) 0.0637(5) Uani 1 1 d F3 F 1.12092(19) 0.60106(8) 0.7667(2) 0.0948(6) Uani 1 1 d N1 N 0.8640(2) 0.68067(7) 0.91697(18) 0.0441(4) Uani 1 1 d F2 F 1.1114(3) 0.51504(9) 0.7316(3) 0.1226(8) Uani 1 1 d C15 C 0.8153(2) 0.66445(7) 0.6293(2) 0.0331(4) Uani 1 1 d C16 C 0.8722(2) 0.69831(8) 0.7643(2) 0.0376(4) Uani 1 1 d C10 C 0.7341(2) 0.60890(7) 0.6408(2) 0.0328(4) Uani 1 1 d C5 C 0.5685(2) 0.60492(7) 0.5015(2) 0.0387(4) Uani 1 1 d C20 C 0.8342(3) 0.68290(9) 0.4842(2) 0.0445(5) Uani 1 1 d C13 C 0.7698(3) 0.63692(8) 0.9385(2) 0.0417(4) Uani 1 1 d C11 C 0.8540(3) 0.56130(9) 0.6304(3) 0.0457(5) Uani 1 1 d C8 C 0.6604(2) 0.60860(7) 0.7885(2) 0.0376(4) Uani 1 1 d C6 C 0.4324(2) 0.62464(8) 0.5507(3) 0.0448(5) Uani 1 1 d C7 C 0.4930(3) 0.64199(9) 0.7229(3) 0.0457(5) Uani 1 1 d C9 C 0.6141(3) 0.55142(9) 0.8324(3) 0.0546(6) Uani 1 1 d C4 C 0.5439(3) 0.58664(8) 0.3451(3) 0.0506(5) Uani 1 1 d C17 C 0.9415(3) 0.74935(9) 0.7490(3) 0.0530(6) Uani 1 1 d C19 C 0.9056(3) 0.73308(10) 0.4712(3) 0.0589(6) Uani 1 1 d C18 C 0.9578(3) 0.76639(10) 0.6033(3) 0.0613(6) Uani 1 1 d C12 C 1.0218(3) 0.55735(10) 0.7567(3) 0.0571(6) Uani 1 1 d C2 C 0.2689(3) 0.62572(10) 0.4433(3) 0.0624(7) Uani 1 1 d C3 C 0.3798(4) 0.58796(10) 0.2389(3) 0.0647(7) Uani 1 1 d C1 C 0.2447(4) 0.60666(11) 0.2883(4) 0.0726(8) Uani 1 1 d C14 C 0.9518(5) 0.71279(12) 1.0589(3) 0.0673(7) Uani 1 1 d H9A H 0.542(3) 0.5331(11) 0.736(3) 0.062(7) Uiso 1 1 d H9B H 0.548(4) 0.5543(13) 0.912(4) 0.095(10) Uiso 1 1 d H9C H 0.715(3) 0.5279(11) 0.875(3) 0.066(7) Uiso 1 1 d H14A H 0.948(4) 0.6905(12) 1.153(4) 0.083(9) Uiso 1 1 d H14B H 1.075(4) 0.7174(12) 1.061(3) 0.086(10) Uiso 1 1 d H14C H 0.893(4) 0.7486(13) 1.057(4) 0.091(10) Uiso 1 1 d H7A H 0.522(3) 0.6841(10) 0.731(3) 0.051(6) Uiso 1 1 d H7B H 0.419(3) 0.6346(10) 0.785(3) 0.061(7) Uiso 1 1 d H20 H 0.794(3) 0.6598(9) 0.389(3) 0.057(6) Uiso 1 1 d H4 H 0.644(3) 0.5717(10) 0.308(3) 0.059(7) Uiso 1 1 d H17 H 0.975(3) 0.7731(11) 0.840(3) 0.066(7) Uiso 1 1 d H1 H 0.130(4) 0.6056(12) 0.211(4) 0.092(9) Uiso 1 1 d H3 H 0.358(4) 0.5731(11) 0.124(3) 0.080(8) Uiso 1 1 d H19 H 0.914(4) 0.7445(11) 0.372(4) 0.081(9) Uiso 1 1 d H2 H 0.176(4) 0.6376(11) 0.483(3) 0.074(8) Uiso 1 1 d H18 H 1.006(4) 0.8022(12) 0.594(3) 0.078(8) Uiso 1 1 d H11A H 0.882(3) 0.5648(9) 0.531(3) 0.050(6) Uiso 1 1 d H11B H 0.795(3) 0.5252(11) 0.627(3) 0.062(7) 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 F1 0.0658(9) 0.1217(14) 0.0606(9) 0.0223(9) 0.0047(7) 0.0118(9) O1 0.0875(12) 0.0710(11) 0.0379(8) 0.0059(7) 0.0261(8) -0.0050(9) F3 0.0435(8) 0.1054(13) 0.1234(15) 0.0286(11) 0.0048(8) -0.0073(8) N1 0.0569(10) 0.0432(9) 0.0310(8) -0.0063(7) 0.0109(7) -0.0068(8) F2 0.0935(13) 0.1218(16) 0.1329(17) -0.0249(13) 0.0016(11) 0.0730(12) C15 0.0325(9) 0.0345(9) 0.0325(9) -0.0022(7) 0.0097(7) 0.0001(7) C16 0.0398(10) 0.0373(10) 0.0358(10) -0.0032(8) 0.0112(8) -0.0042(8) C10 0.0364(9) 0.0294(9) 0.0317(9) -0.0022(7) 0.0087(7) 0.0006(7) C5 0.0423(10) 0.0293(9) 0.0402(10) -0.0011(7) 0.0049(8) -0.0035(8) C20 0.0529(12) 0.0469(11) 0.0372(10) -0.0047(9) 0.0186(9) -0.0064(9) C13 0.0498(11) 0.0435(11) 0.0339(10) 0.0024(8) 0.0156(8) 0.0056(9) C11 0.0498(12) 0.0408(11) 0.0468(12) -0.0033(9) 0.0144(9) 0.0084(9) C8 0.0404(10) 0.0348(9) 0.0404(10) 0.0036(8) 0.0161(8) 0.0000(8) C6 0.0394(10) 0.0363(10) 0.0554(12) 0.0039(9) 0.0085(9) -0.0018(8) C7 0.0407(10) 0.0463(12) 0.0545(12) 0.0019(10) 0.0207(9) 0.0033(9) C9 0.0621(15) 0.0418(12) 0.0632(15) 0.0087(11) 0.0231(12) -0.0068(11) C4 0.0609(13) 0.0382(11) 0.0454(12) -0.0079(9) 0.0036(10) -0.0032(10) C17 0.0616(13) 0.0464(12) 0.0520(13) -0.0126(10) 0.0181(11) -0.0177(10) C19 0.0786(16) 0.0566(14) 0.0505(13) 0.0058(11) 0.0331(12) -0.0139(12) C18 0.0775(16) 0.0465(13) 0.0666(15) -0.0010(11) 0.0314(13) -0.0226(12) C12 0.0472(12) 0.0591(14) 0.0646(15) 0.0046(11) 0.0153(11) 0.0153(11) C2 0.0420(12) 0.0581(14) 0.0781(17) 0.0089(12) 0.0031(12) 0.0019(11) C3 0.0786(17) 0.0479(13) 0.0493(14) -0.0053(11) -0.0109(12) -0.0066(12) C1 0.0585(15) 0.0586(15) 0.0758(18) 0.0049(13) -0.0203(14) -0.0084(12) C14 0.097(2) 0.0609(16) 0.0366(12) -0.0119(11) 0.0072(12) -0.0128(15) 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 C16 N1 C14 118.75(18) C13 N1 C16 123.34(15) C13 N1 C14 117.79(18) C16 C15 C10 121.17(15) C20 C15 C16 118.00(17) C20 C15 C10 120.83(16) C15 C16 N1 120.63(16) C17 C16 N1 119.56(17) C17 C16 C15 119.79(18) C15 C10 C5 107.83(14) C15 C10 C11 111.84(16) C15 C10 C8 109.53(14) C5 C10 C11 109.75(15) C5 C10 C8 100.60(14) C11 C10 C8 116.45(15) C6 C5 C10 109.85(16) C4 C5 C10 129.53(18) C4 C5 C6 120.60(19) C15 C20 H20 118.8(14) C19 C20 C15 121.66(19) C19 C20 H20 119.6(13) O1 C13 N1 121.05(19) O1 C13 C8 121.54(19) N1 C13 C8 117.25(16) C10 C11 H11A 107.7(13) C10 C11 H11B 111.0(14) C12 C11 C10 118.19(18) C12 C11 H11A 105.2(14) C12 C11 H11B 107.2(14) H11A C11 H11B 106.9(19) C13 C8 C10 115.41(15) C13 C8 C7 108.29(16) C13 C8 C9 109.35(17) C7 C8 C10 101.77(15) C9 C8 C10 113.01(17) C9 C8 C7 108.49(17) C5 C6 C7 109.96(17) C5 C6 C2 120.1(2) C2 C6 C7 129.9(2) C8 C7 H7A 109.5(12) C8 C7 H7B 109.6(15) C6 C7 C8 102.73(16) C6 C7 H7A 110.3(12) C6 C7 H7B 116.0(15) H7A C7 H7B 108.6(19) C8 C9 H9A 109.7(15) C8 C9 H9B 109.4(18) C8 C9 H9C 112.8(15) H9A C9 H9B 108(2) H9A C9 H9C 107(2) H9B C9 H9C 110(2) C5 C4 C3 118.7(2) C5 C4 H4 121.0(14) C3 C4 H4 120.2(13) C16 C17 H17 119.5(15) C18 C17 C16 120.6(2) C18 C17 H17 119.8(15) C20 C19 H19 119.5(18) C18 C19 C20 119.9(2) C18 C19 H19 120.6(18) C17 C18 H18 120.1(16) C19 C18 C17 120.0(2) C19 C18 H18 119.9(16) F1 C12 F3 103.2(2) F1 C12 C11 114.65(19) F3 C12 C11 114.2(2) F2 C12 F1 105.9(2) F2 C12 F3 106.5(2) F2 C12 C11 111.5(2) C6 C2 H2 118.2(17) C1 C2 C6 119.0(3) C1 C2 H2 122.7(17) C4 C3 H3 119.8(16) C1 C3 C4 120.6(2) C1 C3 H3 119.5(16) C2 C1 H1 121.0(18) C3 C1 C2 120.9(2) C3 C1 H1 118.1(18) N1 C14 H14A 105.8(17) N1 C14 H14B 108.8(17) N1 C14 H14C 110.0(18) H14A C14 H14B 108(2) H14A C14 H14C 112(2) H14B C14 H14C 112(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance F1 C12 1.328(3) O1 C13 1.222(2) F3 C12 1.330(3) N1 C16 1.414(2) N1 C13 1.363(3) N1 C14 1.464(3) F2 C12 1.323(3) C15 C16 1.401(2) C15 C10 1.529(2) C15 C20 1.388(3) C16 C17 1.394(3) C10 C5 1.537(2) C10 C11 1.542(3) C10 C8 1.567(2) C5 C6 1.390(3) C5 C4 1.388(3) C20 C19 1.379(3) C20 H20 0.97(2) C13 C8 1.519(3) C11 C12 1.493(3) C11 H11A 0.96(2) C11 H11B 1.00(3) C8 C7 1.556(3) C8 C9 1.527(3) C6 C7 1.495(3) C6 C2 1.393(3) C7 H7A 1.06(2) C7 H7B 0.93(3) C9 H9A 0.99(3) C9 H9B 1.00(3) C9 H9C 0.99(3) C4 C3 1.394(3) C4 H4 1.03(2) C17 C18 1.375(3) C17 H17 0.96(3) C19 C18 1.371(3) C19 H19 0.93(3) C18 H18 0.97(3) C2 C1 1.384(4) C2 H2 0.97(3) C3 C1 1.374(4) C3 H3 1.03(3) C1 H1 0.99(3) C14 H14A 0.99(3) C14 H14B 1.01(3) C14 H14C 1.00(3)