# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Deepak Chopra' _publ_contact_author_email dchopra@iiserbhopal.ac.in _publ_author_name 'Deepak Chopra' data_T-0-1 _database_code_depnum_ccdc_archive 'CCDC 826193' #TrackingRef 't-0-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 F3 N O' _chemical_formula_sum 'C14 H10 F3 N O' _chemical_formula_weight 265.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.991(5) _cell_length_b 16.421(5) _cell_length_c 15.645(5) _cell_angle_alpha 90 _cell_angle_beta 108.492(5) _cell_angle_gamma 90 _cell_volume 2434.2(16) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 971 _cell_measurement_theta_min 2.7 _cell_measurement_theta_max 25.4 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.447 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1088 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.982 _exptl_absorpt_correction_T_max 0.990 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23559 _diffrn_reflns_av_R_equivalents 0.0344 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4277 _reflns_number_gt 3517 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0131P)^2^+5.0600P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4277 _refine_ls_number_parameters 423 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0551 _refine_ls_wR_factor_ref 0.1300 _refine_ls_wR_factor_gt 0.1276 _refine_ls_goodness_of_fit_ref 1.269 _refine_ls_restrained_S_all 1.269 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-0-1 in P2(1)/c CELL 0.71073 9.991 16.421 15.645 90.000 108.492 90.000 ZERR 8 0.005 0.005 0.005 0.005 0.005 0.005 LATT 1 SYMM -X, 0.50000+Y, 0.50000-Z SFAC C H N O F UNIT 112 80 8 8 24 MERG 2 L.S. 8 TEMP -153 OMIT -1 50 ACTA BOND $H CONF HTAB FMAP 2 PLAN 15 WGHT 0.013100 5.060000 FVAR 4.24394 C1 1 0.713704 0.162342 1.018959 11.00000 0.01539 0.02163 = 0.01821 -0.00109 0.00275 0.00185 C2 1 0.770793 0.240019 1.040285 11.00000 0.01744 0.02366 = 0.01882 0.00175 0.00271 0.00404 C3 1 0.765578 0.278499 1.118626 11.00000 0.03173 0.02198 = 0.01927 -0.00163 0.00561 0.00116 C4 1 0.703176 0.240601 1.174504 11.00000 0.03509 0.02748 = 0.01926 -0.00113 0.00883 0.00287 C5 1 0.645181 0.164094 1.153807 11.00000 0.02962 0.02877 = 0.02217 0.00251 0.01270 0.00281 C6 1 0.649427 0.125371 1.075802 11.00000 0.02007 0.02320 = 0.02386 0.00083 0.00734 -0.00166 C7 1 0.569248 0.056861 0.793597 11.00000 0.01958 0.01368 = 0.01703 0.00070 0.00682 0.00343 C8 1 0.667268 0.053515 0.747252 11.00000 0.02110 0.01890 = 0.02299 0.00017 0.00893 -0.00009 C9 1 0.629337 0.015780 0.663164 11.00000 0.02773 0.02391 = 0.02378 0.00080 0.01496 0.00623 C10 1 0.497130 -0.018138 0.625618 11.00000 0.03392 0.02110 = 0.01804 -0.00150 0.00753 0.00636 C11 1 0.400339 -0.014463 0.671983 11.00000 0.02341 0.02215 = 0.02135 -0.00164 0.00670 -0.00021 C12 1 0.436255 0.023140 0.755397 11.00000 0.01980 0.01847 = 0.02054 0.00004 0.00817 0.00173 C13 1 0.723327 0.116191 0.937689 11.00000 0.01925 0.01993 = 0.01981 -0.00055 0.00800 0.00042 C14 1 0.834729 0.285270 0.979008 11.00000 0.02979 0.02821 = 0.02526 -0.00056 0.01007 -0.00389 N1 3 0.596184 0.096837 0.878002 11.00000 0.01650 0.02312 = 0.01897 -0.00319 0.00725 0.00008 O1 4 0.837292 0.098094 0.929613 11.00000 0.01671 0.04194 = 0.03212 -0.01093 0.00974 0.00152 F1 5 0.763675 0.272979 0.891599 11.00000 0.06175 0.04268 = 0.01945 -0.00226 0.01522 -0.01432 F2 5 0.969323 0.264644 0.991001 11.00000 0.03101 0.05594 = 0.06066 0.01061 0.02595 -0.00146 F3 5 0.834405 0.366106 0.991525 11.00000 0.06125 0.02568 = 0.03461 0.00094 0.01981 -0.01002 C1' 1 0.265515 0.170634 1.032342 11.00000 0.01278 0.02221 = 0.02023 -0.00009 0.00680 0.00313 C2' 1 0.306511 0.252485 1.042581 11.00000 0.01411 0.02350 = 0.02071 0.00373 0.00675 0.00363 C3' 1 0.338911 0.289720 1.125791 11.00000 0.02538 0.02008 = 0.02499 -0.00232 0.00783 -0.00164 C4' 1 0.331690 0.246352 1.200385 11.00000 0.03149 0.03115 = 0.01790 -0.00349 0.00655 0.00177 C5' 1 0.291207 0.165398 1.191386 11.00000 0.03176 0.03004 = 0.02314 0.00599 0.01448 0.00285 C6' 1 0.257416 0.127704 1.107508 11.00000 0.02327 0.02005 = 0.02759 0.00103 0.00957 0.00203 C7' 1 0.074258 0.047706 0.827174 11.00000 0.01131 0.03220 = 0.02393 -0.00731 0.00377 -0.00016 C8' 1 0.079886 0.083355 0.747819 11.00000 0.02046 0.04137 = 0.02595 -0.00095 0.00271 -0.00011 C9' 1 0.046591 0.037240 0.670011 11.00000 0.02312 0.07077 = 0.02444 -0.00406 0.00482 0.00615 C10' 1 0.008054 -0.043304 0.670895 11.00000 0.01984 0.06586 = 0.03950 -0.02795 0.00470 0.00129 C11' 1 0.001410 -0.078412 0.749665 11.00000 0.02507 0.04038 = 0.04850 -0.01906 0.00814 0.00025 C12' 1 0.034054 -0.033389 0.827976 11.00000 0.01802 0.02960 = 0.03490 -0.00695 0.00522 0.00013 C13' 1 0.239838 0.125966 0.945267 11.00000 0.01614 0.02134 = 0.02483 -0.00029 0.00763 0.00015 C14' 1 0.314679 0.301649 0.964012 11.00000 0.02640 0.02646 = 0.02431 0.00213 0.00702 -0.00170 N1' 3 0.111405 0.094013 0.908874 11.00000 0.01568 0.02857 = 0.02343 -0.00508 0.01020 0.00033 O1' 4 0.334918 0.118095 0.911146 11.00000 0.01674 0.04696 = 0.03218 -0.01346 0.01182 -0.00224 F1' 5 0.210916 0.283287 0.887003 11.00000 0.03643 0.03865 = 0.01879 0.00597 0.00360 0.00034 F2' 5 0.437232 0.292154 0.946492 11.00000 0.03176 0.04687 = 0.03758 0.01256 0.02003 -0.00251 F3' 5 0.302201 0.381706 0.976798 11.00000 0.05302 0.02101 = 0.03612 0.00782 0.01379 -0.00237 H1 2 0.517047 0.105267 0.900870 11.00000 0.04725 H3 2 0.808200 0.331898 1.133446 11.00000 0.03795 H4 2 0.707882 0.270940 1.228956 11.00000 0.02737 H5 2 0.594667 0.136854 1.194802 11.00000 0.04164 H6 2 0.610587 0.069639 1.059209 11.00000 0.03739 H8 2 0.760860 0.075646 0.774705 11.00000 0.03186 H9 2 0.705738 0.009046 0.632015 11.00000 0.03105 H10 2 0.468882 -0.038635 0.571183 11.00000 0.02462 H11 2 0.311182 -0.036198 0.648345 11.00000 0.02018 H12 2 0.372643 0.027668 0.785849 11.00000 0.02027 H1' 2 0.055189 0.101467 0.935060 11.00000 0.01281 H3' 2 0.364086 0.343386 1.131385 11.00000 0.01411 H4' 2 0.347713 0.270122 1.262495 11.00000 0.03609 H5' 2 0.281131 0.135527 1.242940 11.00000 0.02460 H6' 2 0.227041 0.069865 1.105935 11.00000 0.02951 H8' 2 0.110824 0.135943 0.753592 11.00000 0.03090 H9' 2 0.059742 0.067628 0.616263 11.00000 0.03080 H10' 2 -0.013578 -0.074519 0.618942 11.00000 0.06127 H11' 2 -0.023648 -0.137263 0.749859 11.00000 0.05248 H12' 2 0.032819 -0.061397 0.883850 11.00000 0.02825 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.7137(3) 0.16234(19) 1.0190(2) 0.0190(7) Uani 1 1 d . . . C2 C 0.7708(3) 0.2400(2) 1.0403(2) 0.0207(7) Uani 1 1 d . . . C3 C 0.7656(4) 0.2785(2) 1.1186(2) 0.0249(8) Uani 1 1 d . . . C4 C 0.7032(4) 0.2406(2) 1.1745(2) 0.0272(8) Uani 1 1 d . . . C5 C 0.6452(4) 0.1641(2) 1.1538(2) 0.0258(8) Uani 1 1 d . . . C6 C 0.6494(3) 0.1254(2) 1.0758(2) 0.0223(7) Uani 1 1 d . . . C7 C 0.5692(3) 0.05686(18) 0.7936(2) 0.0165(7) Uani 1 1 d . . . C8 C 0.6673(4) 0.0535(2) 0.7473(2) 0.0205(7) Uani 1 1 d . . . C9 C 0.6293(4) 0.0158(2) 0.6632(2) 0.0235(7) Uani 1 1 d . . . C10 C 0.4971(4) -0.0181(2) 0.6256(2) 0.0245(8) Uani 1 1 d . . . C11 C 0.4003(4) -0.0145(2) 0.6720(2) 0.0224(7) Uani 1 1 d . . . C12 C 0.4363(3) 0.02314(19) 0.7554(2) 0.0192(7) Uani 1 1 d . . . C13 C 0.7233(3) 0.11619(19) 0.9377(2) 0.0192(7) Uani 1 1 d . . . C14 C 0.8347(4) 0.2853(2) 0.9790(2) 0.0274(8) Uani 1 1 d . . . N1 N 0.5962(3) 0.09684(16) 0.87800(17) 0.0191(6) Uani 1 1 d . . . O1 O 0.8373(2) 0.09809(15) 0.92961(16) 0.0298(6) Uani 1 1 d . . . F1 F 0.7637(2) 0.27298(13) 0.89160(13) 0.0407(6) Uani 1 1 d . . . F2 F 0.9693(2) 0.26464(15) 0.99100(16) 0.0465(6) Uani 1 1 d . . . F3 F 0.8344(2) 0.36611(12) 0.99152(14) 0.0394(6) Uani 1 1 d . . . C1' C 0.2655(3) 0.17063(19) 1.0323(2) 0.0180(7) Uani 1 1 d . . . C2' C 0.3065(3) 0.2525(2) 1.0426(2) 0.0191(7) Uani 1 1 d . . . C3' C 0.3389(4) 0.2897(2) 1.1258(2) 0.0235(7) Uani 1 1 d . . . C4' C 0.3317(4) 0.2464(2) 1.2004(2) 0.0271(8) Uani 1 1 d . . . C5' C 0.2912(4) 0.1654(2) 1.1914(2) 0.0270(8) Uani 1 1 d . . . C6' C 0.2574(3) 0.1277(2) 1.1075(2) 0.0233(7) Uani 1 1 d . . . C7' C 0.0743(3) 0.0477(2) 0.8272(2) 0.0229(7) Uani 1 1 d . . . C8' C 0.0799(4) 0.0834(3) 0.7478(2) 0.0304(8) Uani 1 1 d . . . C9' C 0.0466(4) 0.0372(3) 0.6700(3) 0.0401(10) Uani 1 1 d . . . C10' C 0.0081(4) -0.0433(3) 0.6709(3) 0.0428(11) Uani 1 1 d . . . C11' C 0.0014(4) -0.0784(3) 0.7497(3) 0.0388(10) Uani 1 1 d . . . C12' C 0.0341(3) -0.0334(2) 0.8280(3) 0.0283(8) Uani 1 1 d . . . C13' C 0.2398(3) 0.1260(2) 0.9453(2) 0.0205(7) Uani 1 1 d . . . C14' C 0.3147(4) 0.3016(2) 0.9640(2) 0.0260(8) Uani 1 1 d . . . N1' N 0.1114(3) 0.09401(17) 0.90887(19) 0.0216(6) Uani 1 1 d . . . O1' O 0.3349(2) 0.11810(16) 0.91115(16) 0.0310(6) Uani 1 1 d . . . F1' F 0.2109(2) 0.28329(13) 0.88700(12) 0.0325(5) Uani 1 1 d . . . F2' F 0.4372(2) 0.29215(13) 0.94649(14) 0.0366(5) Uani 1 1 d . . . F3' F 0.3022(2) 0.38171(12) 0.97680(14) 0.0368(5) Uani 1 1 d . . . H1 H 0.517(4) 0.105(2) 0.901(3) 0.047(12) Uiso 1 1 d . . . H3 H 0.808(4) 0.332(2) 1.133(3) 0.038(11) Uiso 1 1 d . . . H4 H 0.708(4) 0.271(2) 1.229(2) 0.027(9) Uiso 1 1 d . . . H5 H 0.595(4) 0.137(2) 1.195(3) 0.042(11) Uiso 1 1 d . . . H6 H 0.611(4) 0.070(2) 1.059(3) 0.037(11) Uiso 1 1 d . . . H8 H 0.761(4) 0.076(2) 0.775(2) 0.032(10) Uiso 1 1 d . . . H9 H 0.706(4) 0.009(2) 0.632(2) 0.031(10) Uiso 1 1 d . . . H10 H 0.469(4) -0.039(2) 0.571(2) 0.025(9) Uiso 1 1 d . . . H11 H 0.311(4) -0.036(2) 0.648(2) 0.020(9) Uiso 1 1 d . . . H12 H 0.373(4) 0.028(2) 0.786(2) 0.020(9) Uiso 1 1 d . . . H1' H 0.055(3) 0.101(2) 0.935(2) 0.013(9) Uiso 1 1 d . . . H3' H 0.364(3) 0.343(2) 1.131(2) 0.014(8) Uiso 1 1 d . . . H4' H 0.348(4) 0.270(2) 1.262(3) 0.036(10) Uiso 1 1 d . . . H5' H 0.281(3) 0.136(2) 1.243(2) 0.025(9) Uiso 1 1 d . . . H6' H 0.227(4) 0.070(2) 1.106(2) 0.030(10) Uiso 1 1 d . . . H8' H 0.111(4) 0.136(2) 0.754(2) 0.031(10) Uiso 1 1 d . . . H9' H 0.060(4) 0.068(2) 0.616(3) 0.031(10) Uiso 1 1 d . . . H10' H -0.014(5) -0.075(3) 0.619(3) 0.061(14) Uiso 1 1 d . . . H11' H -0.024(4) -0.137(3) 0.750(3) 0.052(13) Uiso 1 1 d . . . H12' H 0.033(4) -0.061(2) 0.884(2) 0.028(10) 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 C1 0.0154(16) 0.0216(17) 0.0182(16) -0.0011(13) 0.0028(13) 0.0018(13) C2 0.0174(16) 0.0237(17) 0.0188(16) 0.0018(14) 0.0027(13) 0.0040(14) C3 0.0317(19) 0.0220(18) 0.0193(17) -0.0016(14) 0.0056(14) 0.0012(15) C4 0.035(2) 0.0275(19) 0.0193(18) -0.0011(15) 0.0088(15) 0.0029(16) C5 0.0296(19) 0.0288(19) 0.0222(18) 0.0025(15) 0.0127(15) 0.0028(16) C6 0.0201(17) 0.0232(18) 0.0239(18) 0.0008(14) 0.0073(14) -0.0017(14) C7 0.0196(16) 0.0137(15) 0.0170(15) 0.0007(12) 0.0068(13) 0.0034(13) C8 0.0211(17) 0.0189(17) 0.0230(17) 0.0002(14) 0.0089(14) -0.0001(14) C9 0.0277(19) 0.0239(18) 0.0238(18) 0.0008(14) 0.0150(15) 0.0062(15) C10 0.034(2) 0.0211(18) 0.0180(18) -0.0015(14) 0.0075(15) 0.0064(15) C11 0.0234(18) 0.0221(17) 0.0214(17) -0.0016(14) 0.0067(14) -0.0002(15) C12 0.0198(17) 0.0185(16) 0.0205(17) 0.0000(13) 0.0082(14) 0.0017(13) C13 0.0192(17) 0.0199(17) 0.0198(16) -0.0005(13) 0.0080(13) 0.0004(13) C14 0.030(2) 0.0282(19) 0.0253(19) -0.0006(15) 0.0101(15) -0.0039(16) N1 0.0165(14) 0.0231(15) 0.0190(14) -0.0032(11) 0.0072(11) 0.0001(11) O1 0.0167(12) 0.0419(15) 0.0321(14) -0.0109(12) 0.0097(10) 0.0015(11) F1 0.0617(15) 0.0427(13) 0.0194(11) -0.0023(10) 0.0152(10) -0.0143(11) F2 0.0310(13) 0.0559(15) 0.0607(15) 0.0106(13) 0.0260(11) -0.0015(11) F3 0.0612(15) 0.0257(11) 0.0346(12) 0.0009(9) 0.0198(11) -0.0100(10) C1' 0.0128(15) 0.0222(17) 0.0202(16) -0.0001(13) 0.0068(13) 0.0031(13) C2' 0.0141(15) 0.0235(17) 0.0207(17) 0.0037(14) 0.0068(13) 0.0036(13) C3' 0.0254(18) 0.0201(18) 0.0250(18) -0.0023(14) 0.0078(14) -0.0016(15) C4' 0.0315(19) 0.031(2) 0.0179(17) -0.0035(15) 0.0066(14) 0.0018(16) C5' 0.032(2) 0.030(2) 0.0231(18) 0.0060(16) 0.0145(15) 0.0029(16) C6' 0.0233(18) 0.0201(18) 0.0276(19) 0.0010(15) 0.0096(14) 0.0020(14) C7' 0.0113(15) 0.0322(19) 0.0239(18) -0.0073(15) 0.0038(13) -0.0002(14) C8' 0.0205(18) 0.041(2) 0.0260(19) -0.0009(17) 0.0027(15) -0.0001(17) C9' 0.023(2) 0.071(3) 0.024(2) -0.004(2) 0.0048(16) 0.006(2) C10' 0.0198(19) 0.066(3) 0.040(2) -0.028(2) 0.0047(17) 0.0013(19) C11' 0.0251(19) 0.040(2) 0.048(3) -0.019(2) 0.0081(17) 0.0002(18) C12' 0.0180(18) 0.030(2) 0.035(2) -0.0070(17) 0.0052(15) 0.0001(15) C13' 0.0161(16) 0.0213(17) 0.0248(17) -0.0003(14) 0.0076(14) 0.0001(13) C14' 0.0264(19) 0.0265(19) 0.0243(18) 0.0021(15) 0.0070(15) -0.0017(15) N1' 0.0157(14) 0.0286(16) 0.0234(15) -0.0051(12) 0.0102(12) 0.0003(12) O1' 0.0167(12) 0.0470(16) 0.0322(14) -0.0135(12) 0.0118(10) -0.0022(11) F1' 0.0364(12) 0.0386(12) 0.0188(10) 0.0060(9) 0.0036(9) 0.0003(10) F2' 0.0318(12) 0.0469(13) 0.0376(12) 0.0126(10) 0.0200(10) -0.0025(10) F3' 0.0530(14) 0.0210(11) 0.0361(12) 0.0078(9) 0.0138(10) -0.0024(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C6 1.391(5) . ? C1 C2 1.394(5) . ? C1 C13 1.509(4) . ? C2 C3 1.395(5) . ? C2 C14 1.506(5) . ? C3 C4 1.373(5) . ? C3 H3 0.97(4) . ? C4 C5 1.378(5) . ? C4 H4 0.98(4) . ? C5 C6 1.389(5) . ? C5 H5 1.04(4) . ? C6 H6 1.00(4) . ? C7 C12 1.388(4) . ? C7 C8 1.392(4) . ? C7 N1 1.422(4) . ? C8 C9 1.394(5) . ? C8 H8 0.97(4) . ? C9 C10 1.381(5) . ? C9 H9 1.03(4) . ? C10 C11 1.382(5) . ? C10 H10 0.88(4) . ? C11 C12 1.384(5) . ? C11 H11 0.92(3) . ? C12 H12 0.91(3) . ? C13 O1 1.221(4) . ? C13 N1 1.354(4) . ? C14 F2 1.341(4) . ? C14 F1 1.341(4) . ? C14 F3 1.342(4) . ? N1 H1 0.98(4) . ? C1' C6' 1.395(5) . ? C1' C2' 1.399(4) . ? C1' C13' 1.496(4) . ? C2' C3' 1.381(5) . ? C2' C14' 1.494(4) . ? C3' C4' 1.388(5) . ? C3' H3' 0.91(3) . ? C4' C5' 1.384(5) . ? C4' H4' 1.01(4) . ? C5' C6' 1.392(5) . ? C5' H5' 0.98(4) . ? C6' H6' 1.00(4) . ? C7' C8' 1.390(5) . ? C7' C12' 1.392(5) . ? C7' N1' 1.431(4) . ? C8' C9' 1.382(5) . ? C8' H8' 0.91(4) . ? C9' C10' 1.379(6) . ? C9' H9' 1.02(4) . ? C10' C11' 1.381(6) . ? C10' H10' 0.93(5) . ? C11' C12' 1.379(5) . ? C11' H11' 1.00(4) . ? C12' H12' 0.99(4) . ? C13' O1' 1.235(4) . ? C13' N1' 1.335(4) . ? C14' F3' 1.341(4) . ? C14' F2' 1.346(4) . ? C14' F1' 1.351(4) . ? N1' H1' 0.80(3) . ? 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 C6 C1 C2 118.9(3) . . ? C6 C1 C13 119.0(3) . . ? C2 C1 C13 122.0(3) . . ? C1 C2 C3 119.9(3) . . ? C1 C2 C14 121.5(3) . . ? C3 C2 C14 118.5(3) . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 121(2) . . ? C2 C3 H3 119(2) . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 115(2) . . ? C5 C4 H4 125(2) . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120(2) . . ? C6 C5 H5 120(2) . . ? C5 C6 C1 120.7(3) . . ? C5 C6 H6 122(2) . . ? C1 C6 H6 117(2) . . ? C12 C7 C8 119.7(3) . . ? C12 C7 N1 117.2(3) . . ? C8 C7 N1 123.0(3) . . ? C7 C8 C9 118.9(3) . . ? C7 C8 H8 120(2) . . ? C9 C8 H8 121(2) . . ? C10 C9 C8 121.2(3) . . ? C10 C9 H9 120(2) . . ? C8 C9 H9 118(2) . . ? C9 C10 C11 119.5(3) . . ? C9 C10 H10 123(2) . . ? C11 C10 H10 118(2) . . ? C10 C11 C12 119.9(3) . . ? C10 C11 H11 121(2) . . ? C12 C11 H11 119(2) . . ? C11 C12 C7 120.7(3) . . ? C11 C12 H12 121(2) . . ? C7 C12 H12 118(2) . . ? O1 C13 N1 124.9(3) . . ? O1 C13 C1 121.3(3) . . ? N1 C13 C1 113.7(3) . . ? F2 C14 F1 106.7(3) . . ? F2 C14 F3 106.1(3) . . ? F1 C14 F3 105.8(3) . . ? F2 C14 C2 113.3(3) . . ? F1 C14 C2 112.4(3) . . ? F3 C14 C2 112.0(3) . . ? C13 N1 C7 127.5(3) . . ? C13 N1 H1 114(2) . . ? C7 N1 H1 118(2) . . ? C6' C1' C2' 118.8(3) . . ? C6' C1' C13' 118.7(3) . . ? C2' C1' C13' 122.3(3) . . ? C3' C2' C1' 120.4(3) . . ? C3' C2' C14' 118.6(3) . . ? C1' C2' C14' 121.0(3) . . ? C2' C3' C4' 120.4(3) . . ? C2' C3' H3' 120(2) . . ? C4' C3' H3' 120(2) . . ? C5' C4' C3' 119.9(3) . . ? C5' C4' H4' 115(2) . . ? C3' C4' H4' 125(2) . . ? C4' C5' C6' 119.9(3) . . ? C4' C5' H5' 120(2) . . ? C6' C5' H5' 120(2) . . ? C5' C6' C1' 120.5(3) . . ? C5' C6' H6' 115(2) . . ? C1' C6' H6' 124(2) . . ? C8' C7' C12' 120.3(3) . . ? C8' C7' N1' 120.1(3) . . ? C12' C7' N1' 119.6(3) . . ? C9' C8' C7' 119.3(4) . . ? C9' C8' H8' 126(2) . . ? C7' C8' H8' 115(2) . . ? C10' C9' C8' 120.5(4) . . ? C10' C9' H9' 126(2) . . ? C8' C9' H9' 114(2) . . ? C9' C10' C11' 120.1(4) . . ? C9' C10' H10' 121(3) . . ? C11' C10' H10' 119(3) . . ? C12' C11' C10' 120.3(4) . . ? C12' C11' H11' 120(3) . . ? C10' C11' H11' 119(3) . . ? C11' C12' C7' 119.5(4) . . ? C11' C12' H12' 118(2) . . ? C7' C12' H12' 122(2) . . ? O1' C13' N1' 122.8(3) . . ? O1' C13' C1' 120.8(3) . . ? N1' C13' C1' 116.4(3) . . ? F3' C14' F2' 106.1(3) . . ? F3' C14' F1' 105.7(3) . . ? F2' C14' F1' 106.4(3) . . ? F3' C14' C2' 112.0(3) . . ? F2' C14' C2' 113.3(3) . . ? F1' C14' C2' 112.7(3) . . ? C13' N1' C7' 122.1(3) . . ? C13' N1' H1' 117(2) . . ? C7' N1' H1' 121(2) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 1.4(5) . . . . ? C13 C1 C2 C3 -176.7(3) . . . . ? C6 C1 C2 C14 -176.6(3) . . . . ? C13 C1 C2 C14 5.2(5) . . . . ? C1 C2 C3 C4 -0.7(5) . . . . ? C14 C2 C3 C4 177.4(3) . . . . ? C2 C3 C4 C5 0.1(5) . . . . ? C3 C4 C5 C6 -0.3(5) . . . . ? C4 C5 C6 C1 1.1(5) . . . . ? C2 C1 C6 C5 -1.7(5) . . . . ? C13 C1 C6 C5 176.5(3) . . . . ? C12 C7 C8 C9 -0.3(5) . . . . ? N1 C7 C8 C9 -177.4(3) . . . . ? C7 C8 C9 C10 -0.1(5) . . . . ? C8 C9 C10 C11 0.2(5) . . . . ? C9 C10 C11 C12 0.1(5) . . . . ? C10 C11 C12 C7 -0.5(5) . . . . ? C8 C7 C12 C11 0.6(5) . . . . ? N1 C7 C12 C11 177.9(3) . . . . ? C6 C1 C13 O1 -117.3(4) . . . . ? C2 C1 C13 O1 60.9(4) . . . . ? C6 C1 C13 N1 61.7(4) . . . . ? C2 C1 C13 N1 -120.1(3) . . . . ? C1 C2 C14 F2 -83.5(4) . . . . ? C3 C2 C14 F2 98.4(4) . . . . ? C1 C2 C14 F1 37.5(4) . . . . ? C3 C2 C14 F1 -140.5(3) . . . . ? C1 C2 C14 F3 156.5(3) . . . . ? C3 C2 C14 F3 -21.6(4) . . . . ? O1 C13 N1 C7 -3.9(5) . . . . ? C1 C13 N1 C7 177.2(3) . . . . ? C12 C7 N1 C13 162.5(3) . . . . ? C8 C7 N1 C13 -20.3(5) . . . . ? C6' C1' C2' C3' 0.3(5) . . . . ? C13' C1' C2' C3' -175.3(3) . . . . ? C6' C1' C2' C14' -179.0(3) . . . . ? C13' C1' C2' C14' 5.4(5) . . . . ? C1' C2' C3' C4' 0.2(5) . . . . ? C14' C2' C3' C4' 179.6(3) . . . . ? C2' C3' C4' C5' -0.3(5) . . . . ? C3' C4' C5' C6' -0.2(5) . . . . ? C4' C5' C6' C1' 0.7(5) . . . . ? C2' C1' C6' C5' -0.8(5) . . . . ? C13' C1' C6' C5' 175.0(3) . . . . ? C12' C7' C8' C9' -0.7(5) . . . . ? N1' C7' C8' C9' 178.6(3) . . . . ? C7' C8' C9' C10' 0.0(5) . . . . ? C8' C9' C10' C11' 0.5(6) . . . . ? C9' C10' C11' C12' -0.4(6) . . . . ? C10' C11' C12' C7' -0.2(5) . . . . ? C8' C7' C12' C11' 0.8(5) . . . . ? N1' C7' C12' C11' -178.5(3) . . . . ? C6' C1' C13' O1' -115.4(4) . . . . ? C2' C1' C13' O1' 60.2(4) . . . . ? C6' C1' C13' N1' 62.9(4) . . . . ? C2' C1' C13' N1' -121.5(3) . . . . ? C3' C2' C14' F3' -23.0(4) . . . . ? C1' C2' C14' F3' 156.3(3) . . . . ? C3' C2' C14' F2' 97.0(4) . . . . ? C1' C2' C14' F2' -83.7(4) . . . . ? C3' C2' C14' F1' -142.1(3) . . . . ? C1' C2' C14' F1' 37.2(4) . . . . ? O1' C13' N1' C7' 0.2(5) . . . . ? C1' C13' N1' C7' -178.1(3) . . . . ? C8' C7' N1' C13' -60.9(4) . . . . ? C12' C7' N1' C13' 118.4(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.234 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.058 # Attachment 't-0-3.cif' data_T-0-3 _database_code_depnum_ccdc_archive 'CCDC 826194' #TrackingRef 't-0-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 F3 N O' _chemical_formula_sum 'C14 H10 F3 N O' _chemical_formula_weight 265.23 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.359(5) _cell_length_b 7.714(5) _cell_length_c 14.242(5) _cell_angle_alpha 77.099(5) _cell_angle_beta 81.606(5) _cell_angle_gamma 89.607(5) _cell_volume 567.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 555 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 25.8 _exptl_crystal_description plates _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.552 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272 _exptl_absorpt_coefficient_mu 0.132 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.972 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12667 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0243 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.71 _diffrn_reflns_theta_max 29.11 _reflns_number_total 2778 _reflns_number_gt 2238 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0528P)^2^+0.1657P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2778 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-0-3 in P -1 CELL 0.71073 5.359 7.714 14.242 77.099 81.606 89.607 ZERR 2 0.005 0.005 0.005 0.005 0.005 0.005 LATT 1 SFAC C H N O F UNIT 28 20 2 2 6 MERG 2 L.S. 12 TEMP -153 ACTA 50 BOND $H CONF HTAB FMAP 2 PLAN 15 WGHT 0.052800 0.165700 FVAR 7.99455 C1 1 0.603922 0.259665 0.633147 11.00000 0.01412 0.01426 = 0.01409 -0.00385 -0.00276 0.00281 C2 1 0.409697 0.179766 0.705943 11.00000 0.01426 0.01821 = 0.01791 -0.00575 -0.00306 -0.00008 C3 1 0.419686 0.181941 0.802502 11.00000 0.01569 0.01790 = 0.01601 -0.00267 0.00049 0.00087 C4 1 0.622339 0.267533 0.825649 11.00000 0.01871 0.01442 = 0.01427 -0.00495 -0.00296 0.00331 C5 1 0.814689 0.350563 0.753495 11.00000 0.01576 0.01642 = 0.01763 -0.00544 -0.00435 0.00018 C6 1 0.806603 0.345164 0.657017 11.00000 0.01340 0.01666 = 0.01551 -0.00342 -0.00097 0.00003 C7 1 0.837989 0.239811 0.371747 11.00000 0.01445 0.01469 = 0.01249 -0.00390 -0.00113 -0.00261 C8 1 0.670324 0.314590 0.309028 11.00000 0.01433 0.01727 = 0.01636 -0.00351 -0.00158 0.00112 C9 1 0.721840 0.308732 0.211204 11.00000 0.01756 0.01917 = 0.01694 -0.00226 -0.00579 -0.00089 C10 1 0.938565 0.230230 0.175540 11.00000 0.01889 0.02105 = 0.01416 -0.00576 -0.00106 -0.00431 C11 1 1.104365 0.155709 0.238710 11.00000 0.01481 0.01951 = 0.01951 -0.00865 0.00034 -0.00006 C12 1 1.055240 0.159807 0.336604 11.00000 0.01540 0.01720 = 0.01769 -0.00476 -0.00464 0.00064 C13 1 0.581112 0.253166 0.530022 11.00000 0.01494 0.01618 = 0.01528 -0.00351 -0.00223 -0.00019 C14 1 0.643827 0.263061 0.929963 11.00000 0.02540 0.01981 = 0.01571 -0.00511 -0.00231 -0.00198 N1 3 0.804737 0.248097 0.471622 11.00000 0.01301 0.02094 = 0.01272 -0.00503 -0.00369 0.00125 O1 4 0.373504 0.249946 0.503419 11.00000 0.01449 0.03945 = 0.01666 -0.00729 -0.00367 -0.00086 F1 5 0.746191 0.412073 0.941747 11.00000 0.06947 0.02973 = 0.02029 -0.00892 -0.00797 -0.01917 F2 5 0.790007 0.130811 0.966249 11.00000 0.07167 0.04020 = 0.02314 -0.00817 -0.02342 0.02200 F3 5 0.422906 0.237518 0.987910 11.00000 0.03716 0.08233 = 0.01968 -0.02187 0.00882 -0.01614 H1 2 0.944741 0.234022 0.500693 11.00000 0.02349 H2 2 0.273045 0.119971 0.689133 11.00000 0.02301 H3 2 0.291889 0.122345 0.852660 11.00000 0.02199 H5 2 0.955262 0.413589 0.769310 11.00000 0.02029 H6 2 0.936094 0.404952 0.607442 11.00000 0.02126 H8 2 0.526730 0.371745 0.331708 11.00000 0.01924 H9 2 0.605727 0.361177 0.169353 11.00000 0.02185 H10 2 0.979223 0.230721 0.107810 11.00000 0.02299 H11 2 1.254648 0.100814 0.215390 11.00000 0.02193 H12 2 1.171707 0.109401 0.381666 11.00000 0.02166 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6039(2) 0.25967(17) 0.63315(9) 0.0140(3) Uani 1 1 d . . . C2 C 0.4097(3) 0.17977(18) 0.70594(9) 0.0165(3) Uani 1 1 d . . . C3 C 0.4197(3) 0.18194(17) 0.80250(10) 0.0170(3) Uani 1 1 d . . . C4 C 0.6223(2) 0.26753(17) 0.82565(9) 0.0155(3) Uani 1 1 d . . . C5 C 0.8147(3) 0.35056(17) 0.75350(9) 0.0162(3) Uani 1 1 d . . . C6 C 0.8066(2) 0.34516(17) 0.65702(9) 0.0153(3) Uani 1 1 d . . . C7 C 0.8380(2) 0.23981(16) 0.37175(9) 0.0138(3) Uani 1 1 d . . . C8 C 0.6703(2) 0.31459(17) 0.30903(9) 0.0161(3) Uani 1 1 d . . . C9 C 0.7218(3) 0.30873(18) 0.21120(9) 0.0178(3) Uani 1 1 d . . . C10 C 0.9386(3) 0.23023(18) 0.17554(9) 0.0179(3) Uani 1 1 d . . . C11 C 1.1044(3) 0.15571(18) 0.23871(10) 0.0176(3) Uani 1 1 d . . . C12 C 1.0552(2) 0.15981(17) 0.33660(9) 0.0164(3) Uani 1 1 d . . . C13 C 0.5811(2) 0.25317(17) 0.53002(9) 0.0155(3) Uani 1 1 d . . . C14 C 0.6438(3) 0.26306(18) 0.92996(10) 0.0202(3) Uani 1 1 d . . . N1 N 0.8047(2) 0.24810(15) 0.47162(8) 0.0152(2) Uani 1 1 d . . . O1 O 0.37350(18) 0.24995(14) 0.50342(7) 0.0232(2) Uani 1 1 d . . . F1 F 0.7462(2) 0.41207(13) 0.94175(6) 0.0391(3) Uani 1 1 d . . . F2 F 0.7900(2) 0.13081(14) 0.96625(7) 0.0433(3) Uani 1 1 d . . . F3 F 0.4229(2) 0.23752(16) 0.98791(7) 0.0460(3) Uani 1 1 d . . . H1 H 0.945(3) 0.234(2) 0.5007(12) 0.023(4) Uiso 1 1 d . . . H2 H 0.273(3) 0.120(2) 0.6891(12) 0.023(4) Uiso 1 1 d . . . H3 H 0.292(3) 0.122(2) 0.8527(12) 0.022(4) Uiso 1 1 d . . . H5 H 0.955(3) 0.414(2) 0.7693(11) 0.020(4) Uiso 1 1 d . . . H6 H 0.936(3) 0.405(2) 0.6074(12) 0.021(4) Uiso 1 1 d . . . H8 H 0.527(3) 0.372(2) 0.3317(11) 0.019(4) Uiso 1 1 d . . . H9 H 0.606(3) 0.361(2) 0.1694(12) 0.022(4) Uiso 1 1 d . . . H10 H 0.979(3) 0.231(2) 0.1078(12) 0.023(4) Uiso 1 1 d . . . H11 H 1.255(3) 0.101(2) 0.2154(12) 0.022(4) Uiso 1 1 d . . . H12 H 1.172(3) 0.109(2) 0.3817(12) 0.022(4) 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 C1 0.0141(6) 0.0143(6) 0.0141(6) -0.0039(4) -0.0028(5) 0.0028(5) C2 0.0143(6) 0.0182(6) 0.0179(6) -0.0058(5) -0.0031(5) -0.0001(5) C3 0.0157(6) 0.0179(6) 0.0160(6) -0.0027(5) 0.0005(5) 0.0009(5) C4 0.0187(7) 0.0144(6) 0.0143(6) -0.0050(5) -0.0030(5) 0.0033(5) C5 0.0158(6) 0.0164(6) 0.0176(6) -0.0054(5) -0.0044(5) 0.0002(5) C6 0.0134(6) 0.0167(6) 0.0155(6) -0.0034(5) -0.0010(5) 0.0000(5) C7 0.0144(6) 0.0147(6) 0.0125(6) -0.0039(4) -0.0011(5) -0.0026(5) C8 0.0143(6) 0.0173(6) 0.0164(6) -0.0035(5) -0.0016(5) 0.0011(5) C9 0.0176(7) 0.0192(6) 0.0169(6) -0.0023(5) -0.0058(5) -0.0009(5) C10 0.0189(7) 0.0210(7) 0.0142(6) -0.0058(5) -0.0011(5) -0.0043(5) C11 0.0148(6) 0.0195(6) 0.0195(6) -0.0087(5) 0.0003(5) -0.0001(5) C12 0.0154(6) 0.0172(6) 0.0177(6) -0.0048(5) -0.0046(5) 0.0006(5) C13 0.0149(6) 0.0162(6) 0.0153(6) -0.0035(5) -0.0022(5) -0.0002(5) C14 0.0254(7) 0.0198(7) 0.0157(6) -0.0051(5) -0.0023(5) -0.0020(5) N1 0.0130(5) 0.0209(6) 0.0127(5) -0.0050(4) -0.0037(4) 0.0013(4) O1 0.0145(5) 0.0395(6) 0.0167(5) -0.0073(4) -0.0037(4) -0.0009(4) F1 0.0695(7) 0.0297(5) 0.0203(4) -0.0089(4) -0.0080(4) -0.0192(5) F2 0.0717(8) 0.0402(6) 0.0231(5) -0.0082(4) -0.0234(5) 0.0220(5) F3 0.0372(6) 0.0823(9) 0.0197(5) -0.0219(5) 0.0088(4) -0.0161(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C2 1.3952(19) . ? C1 C6 1.396(2) . ? C1 C13 1.5033(18) . ? C2 C3 1.3878(19) . ? C2 H2 0.955(17) . ? C3 C4 1.391(2) . ? C3 H3 0.952(17) . ? C4 C5 1.3909(19) . ? C4 C14 1.4995(18) . ? C5 C6 1.3909(18) . ? C5 H5 0.979(17) . ? C6 H6 0.953(17) . ? C7 C8 1.3911(19) . ? C7 C12 1.395(2) . ? C7 N1 1.4232(16) . ? C8 C9 1.3910(18) . ? C8 H8 0.937(17) . ? C9 C10 1.389(2) . ? C9 H9 0.950(17) . ? C10 C11 1.387(2) . ? C10 H10 0.957(17) . ? C11 C12 1.3880(19) . ? C11 H11 0.958(17) . ? C12 H12 0.977(16) . ? C13 O1 1.2287(19) . ? C13 N1 1.3610(19) . ? C14 F3 1.3292(19) . ? C14 F1 1.3312(17) . ? C14 F2 1.3391(18) . ? N1 H1 0.903(17) . ? 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 C2 C1 C6 120.06(12) . . ? C2 C1 C13 117.50(12) . . ? C6 C1 C13 122.43(11) . . ? C3 C2 C1 120.17(13) . . ? C3 C2 H2 120.3(10) . . ? C1 C2 H2 119.5(10) . . ? C2 C3 C4 119.39(12) . . ? C2 C3 H3 120.4(10) . . ? C4 C3 H3 120.2(10) . . ? C5 C4 C3 120.96(12) . . ? C5 C4 C14 118.75(12) . . ? C3 C4 C14 120.21(12) . . ? C6 C5 C4 119.51(12) . . ? C6 C5 H5 119.3(10) . . ? C4 C5 H5 121.2(9) . . ? C5 C6 C1 119.90(12) . . ? C5 C6 H6 119.4(10) . . ? C1 C6 H6 120.6(10) . . ? C8 C7 C12 120.14(12) . . ? C8 C7 N1 122.63(12) . . ? C12 C7 N1 117.16(11) . . ? C9 C8 C7 119.34(12) . . ? C9 C8 H8 120.0(10) . . ? C7 C8 H8 120.6(10) . . ? C10 C9 C8 120.86(12) . . ? C10 C9 H9 121.0(10) . . ? C8 C9 H9 118.2(10) . . ? C11 C10 C9 119.37(13) . . ? C11 C10 H10 119.3(10) . . ? C9 C10 H10 121.3(10) . . ? C10 C11 C12 120.49(13) . . ? C10 C11 H11 120.5(10) . . ? C12 C11 H11 119.0(10) . . ? C11 C12 C7 119.80(12) . . ? C11 C12 H12 121.3(9) . . ? C7 C12 H12 118.9(9) . . ? O1 C13 N1 124.22(13) . . ? O1 C13 C1 121.02(11) . . ? N1 C13 C1 114.75(12) . . ? F3 C14 F1 106.62(12) . . ? F3 C14 F2 106.26(13) . . ? F1 C14 F2 106.25(13) . . ? F3 C14 C4 113.10(12) . . ? F1 C14 C4 112.86(11) . . ? F2 C14 C4 111.27(11) . . ? C13 N1 C7 126.51(12) . . ? C13 N1 H1 116.9(11) . . ? C7 N1 H1 116.1(10) . . ? 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 C6 C1 C2 C3 -1.27(19) . . . . ? C13 C1 C2 C3 -179.79(11) . . . . ? C1 C2 C3 C4 1.29(19) . . . . ? C2 C3 C4 C5 -0.07(19) . . . . ? C2 C3 C4 C14 -176.72(12) . . . . ? C3 C4 C5 C6 -1.17(19) . . . . ? C14 C4 C5 C6 175.52(12) . . . . ? C4 C5 C6 C1 1.19(19) . . . . ? C2 C1 C6 C5 0.01(19) . . . . ? C13 C1 C6 C5 178.46(11) . . . . ? C12 C7 C8 C9 -0.04(19) . . . . ? N1 C7 C8 C9 176.88(12) . . . . ? C7 C8 C9 C10 -0.3(2) . . . . ? C8 C9 C10 C11 0.5(2) . . . . ? C9 C10 C11 C12 -0.2(2) . . . . ? C10 C11 C12 C7 -0.2(2) . . . . ? C8 C7 C12 C11 0.30(19) . . . . ? N1 C7 C12 C11 -176.79(11) . . . . ? C2 C1 C13 O1 29.97(18) . . . . ? C6 C1 C13 O1 -148.52(14) . . . . ? C2 C1 C13 N1 -148.93(12) . . . . ? C6 C1 C13 N1 32.59(17) . . . . ? C5 C4 C14 F3 158.51(12) . . . . ? C3 C4 C14 F3 -24.77(18) . . . . ? C5 C4 C14 F1 37.36(17) . . . . ? C3 C4 C14 F1 -145.91(13) . . . . ? C5 C4 C14 F2 -81.98(16) . . . . ? C3 C4 C14 F2 94.75(16) . . . . ? O1 C13 N1 C7 0.5(2) . . . . ? C1 C13 N1 C7 179.38(11) . . . . ? C8 C7 N1 C13 30.4(2) . . . . ? C12 C7 N1 C13 -152.58(13) . . . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.398 _refine_diff_density_min -0.230 _refine_diff_density_rms 0.048 # Attachment 't-1-0.cif' data_T-1-0 _database_code_depnum_ccdc_archive 'CCDC 826195' #TrackingRef 't-1-0.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 F3 N O' _chemical_formula_sum 'C14 H10 F3 N O' _chemical_formula_weight 265.23 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' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_Hall 'P 4w' _symmetry_space_group_name_H-M 'P 41' _symmetry_Int_Tables_number 76 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y, x, z+1/4' 'y, -x, z+3/4' _cell_length_a 9.052(5) _cell_length_b 9.052(5) _cell_length_c 15.156(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1241.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 696 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 25.2 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.120 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9372 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14952 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.62 _diffrn_reflns_theta_max 29.33 _reflns_number_total 3075 _reflns_number_gt 2583 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3075 _refine_ls_number_parameters 212 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0334 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0714 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_restrained_S_all 1.014 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-1-0 in P 41 CELL 0.71073 9.052 9.052 15.156 90.000 90.000 90.000 ZERR 4 0.005 0.005 0.005 0.005 0.005 0.005 LATT -1 SYMM -X,-Y, 0.50000+Z SYMM -Y,X, 0.25000+Z SYMM Y,-X, 0.75000+Z SFAC C H N O F UNIT 56 40 4 4 12 MERG 2 L.S. 12 TEMP -153 ACTA 50 BOND $H CONF HTAB FMAP 2 PLAN 15 WGHT 0.042000 FVAR 8.64393 C1 1 -0.239753 0.239375 0.636815 11.00000 0.02282 0.01816 = 0.01645 -0.00415 -0.00040 0.00156 C2 1 -0.391009 0.206638 0.634332 11.00000 0.02345 0.02892 = 0.02601 -0.00383 -0.00057 -0.00068 C3 1 -0.480399 0.268049 0.569681 11.00000 0.02244 0.04057 = 0.03220 -0.01016 -0.00604 0.00284 C4 1 -0.421687 0.364756 0.508055 11.00000 0.03666 0.03347 = 0.02588 -0.00595 -0.01163 0.01193 C5 1 -0.272241 0.398486 0.510396 11.00000 0.03637 0.02429 = 0.02462 0.00343 -0.00228 0.00451 C6 1 -0.181404 0.335994 0.574127 11.00000 0.02444 0.02170 = 0.02210 -0.00042 -0.00155 0.00123 C7 1 0.096939 0.091938 0.753952 11.00000 0.02285 0.03027 = 0.01537 0.00048 0.00222 0.00826 C8 1 0.082924 -0.058428 0.771181 11.00000 0.04096 0.02905 = 0.02614 0.00019 0.00444 0.00834 C9 1 0.184777 -0.130262 0.824269 11.00000 0.05205 0.03903 = 0.03782 0.01274 0.00897 0.02114 C10 1 0.301151 -0.053630 0.859822 11.00000 0.03529 0.06698 = 0.03713 0.02195 0.00734 0.02651 C11 1 0.316464 0.096372 0.844342 11.00000 0.02162 0.06999 = 0.02790 0.00675 -0.00201 0.00462 C12 1 0.212816 0.171231 0.792048 11.00000 0.02010 0.04264 = 0.01833 0.00240 0.00343 0.00467 C13 1 -0.148761 0.173272 0.708681 11.00000 0.02340 0.01519 = 0.01765 -0.00079 -0.00058 -0.00151 C14 1 0.223804 0.334246 0.779072 11.00000 0.02550 0.04719 = 0.02790 -0.00814 0.00078 -0.00590 N1 3 -0.002486 0.162254 0.694233 11.00000 0.02215 0.02850 = 0.01401 0.00246 -0.00051 0.00273 O1 4 -0.206977 0.133845 0.778685 11.00000 0.02837 0.03149 = 0.01987 0.00444 0.00451 0.00401 F1 5 0.339672 0.393572 0.821800 11.00000 0.04302 0.07032 = 0.05063 -0.00837 -0.00849 -0.02667 F2 5 0.103852 0.406631 0.809176 11.00000 0.04198 0.03929 = 0.06204 -0.01759 0.01149 -0.00094 F3 5 0.238088 0.373536 0.693980 11.00000 0.05397 0.03774 = 0.03174 0.00353 0.00174 -0.00649 H1 2 0.023512 0.174613 0.641534 11.00000 0.02812 H2 2 -0.431972 0.135558 0.680034 11.00000 0.03126 H3 2 -0.586915 0.250991 0.569078 11.00000 0.03034 H4 2 -0.488193 0.405078 0.466723 11.00000 0.04155 H5 2 -0.230179 0.473545 0.467590 11.00000 0.04609 H6 2 -0.074634 0.361164 0.571969 11.00000 0.02797 H8 2 0.004558 -0.108850 0.743388 11.00000 0.04514 H9 2 0.181284 -0.236089 0.836515 11.00000 0.05061 H10 2 0.379136 -0.100754 0.898583 11.00000 0.05165 H11 2 0.392038 0.155144 0.867792 11.00000 0.03986 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.23975(15) 0.23937(14) 0.63682(9) 0.0191(3) Uani 1 1 d . . . C2 C -0.39101(15) 0.20664(17) 0.63433(11) 0.0261(3) Uani 1 1 d . . . C3 C -0.48040(17) 0.26805(18) 0.56968(11) 0.0317(4) Uani 1 1 d . . . C4 C -0.42169(19) 0.36476(18) 0.50806(11) 0.0320(4) Uani 1 1 d . . . C5 C -0.27224(17) 0.39849(16) 0.51040(10) 0.0284(3) Uani 1 1 d . . . C6 C -0.18140(15) 0.33599(15) 0.57413(10) 0.0227(3) Uani 1 1 d . . . C7 C 0.09694(15) 0.09194(16) 0.75395(9) 0.0228(3) Uani 1 1 d . . . C8 C 0.0829(2) -0.05843(18) 0.77118(11) 0.0320(4) Uani 1 1 d . . . C9 C 0.1848(2) -0.1303(2) 0.82427(12) 0.0430(4) Uani 1 1 d . . . C10 C 0.3012(2) -0.0536(2) 0.85982(12) 0.0465(5) Uani 1 1 d . . . C11 C 0.31646(18) 0.0964(2) 0.84434(12) 0.0398(4) Uani 1 1 d . . . C12 C 0.21282(15) 0.17123(17) 0.79205(10) 0.0270(3) Uani 1 1 d . . . C13 C -0.14876(15) 0.17327(14) 0.70868(9) 0.0187(3) Uani 1 1 d . . . C14 C 0.22380(16) 0.33425(19) 0.77907(11) 0.0335(4) Uani 1 1 d . . . N1 N -0.00249(12) 0.16225(13) 0.69423(8) 0.0216(2) Uani 1 1 d . . . O1 O -0.20698(11) 0.13384(11) 0.77868(6) 0.0266(2) Uani 1 1 d . . . F1 F 0.33967(11) 0.39357(14) 0.82180(8) 0.0547(3) Uani 1 1 d . . . F2 F 0.10385(11) 0.40663(11) 0.80918(8) 0.0478(3) Uani 1 1 d . . . F3 F 0.23809(11) 0.37354(10) 0.69398(6) 0.0411(3) Uani 1 1 d . . . H1 H 0.0235(18) 0.1746(18) 0.6415(14) 0.028(4) Uiso 1 1 d . . . H2 H -0.4320(18) 0.136(2) 0.6800(12) 0.031(4) Uiso 1 1 d . . . H3 H -0.5869(19) 0.2510(17) 0.5691(11) 0.030(4) Uiso 1 1 d . . . H4 H -0.488(2) 0.4051(19) 0.4667(13) 0.042(5) Uiso 1 1 d . . . H5 H -0.230(2) 0.474(2) 0.4676(14) 0.046(5) Uiso 1 1 d . . . H6 H -0.0746(19) 0.3612(17) 0.5720(11) 0.028(4) Uiso 1 1 d . . . H8 H 0.005(2) -0.109(2) 0.7434(14) 0.045(5) Uiso 1 1 d . . . H9 H 0.181(2) -0.236(2) 0.8365(15) 0.051(5) Uiso 1 1 d . . . H10 H 0.379(2) -0.101(2) 0.8986(15) 0.052(5) Uiso 1 1 d . . . H11 H 0.392(2) 0.155(2) 0.8678(13) 0.040(5) 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 C1 0.0228(7) 0.0182(6) 0.0165(6) -0.0042(5) -0.0004(6) 0.0016(5) C2 0.0234(7) 0.0289(7) 0.0260(7) -0.0038(7) -0.0006(6) -0.0007(6) C3 0.0224(7) 0.0406(9) 0.0322(8) -0.0102(7) -0.0060(7) 0.0028(7) C4 0.0367(8) 0.0335(8) 0.0259(8) -0.0060(7) -0.0116(7) 0.0119(7) C5 0.0364(8) 0.0243(7) 0.0246(8) 0.0034(6) -0.0023(7) 0.0045(7) C6 0.0244(7) 0.0217(7) 0.0221(7) -0.0004(6) -0.0016(6) 0.0012(6) C7 0.0228(7) 0.0303(7) 0.0154(6) 0.0005(6) 0.0022(5) 0.0083(6) C8 0.0410(9) 0.0291(8) 0.0261(8) 0.0002(7) 0.0044(7) 0.0083(7) C9 0.0521(11) 0.0390(10) 0.0378(10) 0.0127(8) 0.0090(9) 0.0211(8) C10 0.0353(9) 0.0670(13) 0.0371(10) 0.0219(9) 0.0073(8) 0.0265(9) C11 0.0216(8) 0.0700(13) 0.0279(9) 0.0067(9) -0.0020(7) 0.0046(8) C12 0.0201(7) 0.0426(8) 0.0183(7) 0.0024(7) 0.0034(6) 0.0047(6) C13 0.0234(6) 0.0152(6) 0.0177(7) -0.0008(5) -0.0006(5) -0.0015(5) C14 0.0255(7) 0.0472(9) 0.0279(8) -0.0081(7) 0.0008(7) -0.0059(7) N1 0.0221(6) 0.0285(6) 0.0140(6) 0.0025(5) -0.0005(5) 0.0027(5) O1 0.0284(5) 0.0315(5) 0.0199(5) 0.0044(4) 0.0045(4) 0.0040(4) F1 0.0430(6) 0.0703(7) 0.0506(7) -0.0084(6) -0.0085(5) -0.0267(5) F2 0.0420(6) 0.0393(5) 0.0620(7) -0.0176(5) 0.0115(5) -0.0009(4) F3 0.0540(6) 0.0377(5) 0.0317(5) 0.0035(4) 0.0017(5) -0.0065(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C6 1.395(2) . ? C1 C2 1.401(2) . ? C1 C13 1.491(2) . ? C2 C3 1.387(2) . ? C2 H2 1.016(18) . ? C3 C4 1.386(3) . ? C3 H3 0.977(17) . ? C4 C5 1.387(2) . ? C4 H4 0.94(2) . ? C5 C6 1.389(2) . ? C5 H5 1.01(2) . ? C6 H6 0.994(17) . ? C7 C8 1.392(2) . ? C7 C12 1.396(2) . ? C7 N1 1.4263(18) . ? C8 C9 1.386(3) . ? C8 H8 0.94(2) . ? C9 C10 1.372(3) . ? C9 H9 0.98(2) . ? C10 C11 1.385(3) . ? C10 H10 1.01(2) . ? C11 C12 1.403(2) . ? C11 H11 0.937(19) . ? C12 C14 1.492(2) . ? C13 O1 1.2372(17) . ? C13 N1 1.3458(19) . ? C14 F3 1.344(2) . ? C14 F1 1.3445(18) . ? C14 F2 1.348(2) . ? N1 H1 0.84(2) . ? 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 C6 C1 C2 118.96(13) . . ? C6 C1 C13 122.68(12) . . ? C2 C1 C13 118.33(12) . . ? C3 C2 C1 120.28(15) . . ? C3 C2 H2 121.5(9) . . ? C1 C2 H2 118.2(9) . . ? C4 C3 C2 120.36(15) . . ? C4 C3 H3 118.2(10) . . ? C2 C3 H3 121.3(10) . . ? C3 C4 C5 119.71(15) . . ? C3 C4 H4 116.6(11) . . ? C5 C4 H4 123.7(11) . . ? C4 C5 C6 120.36(15) . . ? C4 C5 H5 119.8(11) . . ? C6 C5 H5 119.7(11) . . ? C5 C6 C1 120.32(14) . . ? C5 C6 H6 117.4(10) . . ? C1 C6 H6 122.3(10) . . ? C8 C7 C12 119.59(14) . . ? C8 C7 N1 119.87(14) . . ? C12 C7 N1 120.47(13) . . ? C9 C8 C7 120.48(18) . . ? C9 C8 H8 122.2(12) . . ? C7 C8 H8 117.3(12) . . ? C10 C9 C8 120.12(17) . . ? C10 C9 H9 116.5(13) . . ? C8 C9 H9 123.3(13) . . ? C9 C10 C11 120.41(16) . . ? C9 C10 H10 123.4(12) . . ? C11 C10 H10 116.2(12) . . ? C10 C11 C12 120.16(17) . . ? C10 C11 H11 124.5(11) . . ? C12 C11 H11 115.4(12) . . ? C7 C12 C11 119.20(15) . . ? C7 C12 C14 120.27(13) . . ? C11 C12 C14 120.51(15) . . ? O1 C13 N1 122.49(13) . . ? O1 C13 C1 120.46(12) . . ? N1 C13 C1 117.03(12) . . ? F3 C14 F1 106.34(13) . . ? F3 C14 F2 105.88(14) . . ? F1 C14 F2 105.74(13) . . ? F3 C14 C12 113.24(14) . . ? F1 C14 C12 112.55(14) . . ? F2 C14 C12 112.49(13) . . ? C13 N1 C7 123.41(13) . . ? C13 N1 H1 114.9(11) . . ? C7 N1 H1 119.1(11) . . ? 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 C6 C1 C2 C3 0.9(2) . . . . ? C13 C1 C2 C3 178.72(13) . . . . ? C1 C2 C3 C4 -1.4(2) . . . . ? C2 C3 C4 C5 0.9(2) . . . . ? C3 C4 C5 C6 0.0(2) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? C2 C1 C6 C5 0.0(2) . . . . ? C13 C1 C6 C5 -177.74(13) . . . . ? C12 C7 C8 C9 -1.4(2) . . . . ? N1 C7 C8 C9 175.55(14) . . . . ? C7 C8 C9 C10 -0.5(3) . . . . ? C8 C9 C10 C11 1.2(3) . . . . ? C9 C10 C11 C12 0.0(3) . . . . ? C8 C7 C12 C11 2.5(2) . . . . ? N1 C7 C12 C11 -174.42(13) . . . . ? C8 C7 C12 C14 -175.98(14) . . . . ? N1 C7 C12 C14 7.1(2) . . . . ? C10 C11 C12 C7 -1.8(2) . . . . ? C10 C11 C12 C14 176.64(16) . . . . ? C6 C1 C13 O1 154.04(13) . . . . ? C2 C1 C13 O1 -23.72(19) . . . . ? C6 C1 C13 N1 -24.52(19) . . . . ? C2 C1 C13 N1 157.73(12) . . . . ? C7 C12 C14 F3 -60.78(18) . . . . ? C11 C12 C14 F3 120.80(16) . . . . ? C7 C12 C14 F1 178.56(13) . . . . ? C11 C12 C14 F1 0.1(2) . . . . ? C7 C12 C14 F2 59.2(2) . . . . ? C11 C12 C14 F2 -119.19(16) . . . . ? O1 C13 N1 C7 6.2(2) . . . . ? C1 C13 N1 C7 -175.30(12) . . . . ? C8 C7 N1 C13 63.59(19) . . . . ? C12 C7 N1 C13 -119.53(15) . . . . ? _diffrn_measured_fraction_theta_max 0.935 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.157 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.038 # Attachment 't-2-0.cif' data_T-2-0 _database_code_depnum_ccdc_archive 'CCDC 826196' #TrackingRef 't-2-0.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H10 F3 N O' _chemical_formula_sum 'C14 H10 F3 N O' _chemical_formula_weight 265.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.8471(4) _cell_length_b 8.6097(2) _cell_length_c 10.0943(3) _cell_angle_alpha 90 _cell_angle_beta 100.131(3) _cell_angle_gamma 90 _cell_volume 1184.67(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 635 _cell_measurement_theta_min 1.7 _cell_measurement_theta_max 25.1 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.487 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.126 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9342 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19628 _diffrn_reflns_av_R_equivalents 0.0427 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 32.84 _reflns_number_total 4111 _reflns_number_gt 3074 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0532P)^2^+0.4299P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4111 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0706 _refine_ls_R_factor_gt 0.0492 _refine_ls_wR_factor_ref 0.1297 _refine_ls_wR_factor_gt 0.1127 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-2-0 in P2(1)/c CELL 0.71073 13.847137 8.609691 10.094271 90.0000 100.1309 90.0000 ZERR 4.00 0.000403 0.000238 0.000265 0.0000 0.0026 0.0000 LATT 1 SYMM -X, 0.50000+Y, 0.50000-Z SFAC C H N O F UNIT 56 40 4 4 12 MERG 2 L.S. 12 temp -153 ACTA 50 HTAB BOND $H CONF FMAP 2 PLAN 15 WGHT 0.053200 0.429900 FVAR 8.43617 0.57004 C1 1 0.455736 0.295665 0.028159 11.00000 0.01887 0.01962 = 0.01522 0.00236 0.00429 -0.00049 C2 1 0.414082 0.416092 0.091260 11.00000 0.02375 0.02247 = 0.01717 0.00067 0.00609 -0.00057 C3 1 0.319334 0.465213 0.041270 11.00000 0.02391 0.02391 = 0.02506 0.00272 0.00962 0.00294 C4 1 0.265700 0.395192 -0.071996 11.00000 0.01873 0.02889 = 0.02717 0.00653 0.00317 0.00190 C5 1 0.306909 0.276229 -0.135789 11.00000 0.02222 0.02745 = 0.02297 0.00024 -0.00067 -0.00240 C6 1 0.401425 0.226448 -0.085880 11.00000 0.02167 0.02082 = 0.01913 -0.00100 0.00275 -0.00107 C7 1 0.705056 0.117779 0.027206 11.00000 0.01843 0.02030 = 0.01668 0.00246 0.00412 0.00062 C8 1 0.768095 0.135056 0.150258 11.00000 0.02051 0.02364 = 0.01726 -0.00032 0.00376 -0.00144 C9 1 0.858741 0.060965 0.168547 11.00000 0.01752 0.02832 = 0.02092 0.00262 0.00151 -0.00151 C10 1 0.888636 -0.025922 0.067985 11.00000 0.01931 0.03205 = 0.02788 0.00331 0.00541 0.00400 C11 1 0.826540 -0.038236 -0.055366 11.00000 0.02730 0.03138 = 0.02280 -0.00123 0.00954 0.00555 C12 1 0.735284 0.032469 -0.075667 11.00000 0.02504 0.02749 = 0.01702 0.00074 0.00501 0.00223 C13 1 0.556405 0.242139 0.088071 11.00000 0.02020 0.01969 = 0.01469 0.00129 0.00373 -0.00051 C14 1 0.925082 0.070185 0.302754 11.00000 0.01979 0.04232 = 0.02767 -0.00209 -0.00024 0.00249 N1 3 0.610017 0.183028 -0.000525 11.00000 0.01951 0.02346 = 0.01239 0.00114 0.00183 0.00271 O1 4 0.587055 0.250798 0.210146 11.00000 0.02337 0.03785 = 0.01278 -0.00159 0.00234 0.00288 PART 1 F1A 5 1.017741 0.085963 0.295854 21.00000 0.01215 0.15383 = 0.03378 0.00512 0.00120 0.00531 F2A 5 0.916536 -0.058013 0.374347 21.00000 0.05528 0.06600 = 0.02615 0.01996 -0.01171 -0.01245 F3A 5 0.903812 0.183558 0.380294 21.00000 0.06140 0.06459 = 0.06591 -0.03773 -0.02969 0.02075 PART 2 F1B 5 0.894075 0.163976 0.388537 -21.00000 0.02289 0.10731 = 0.01743 -0.01919 -0.00615 0.01964 F2B 5 1.012579 0.123239 0.287628 -21.00000 0.03635 0.17041 = 0.05551 -0.02686 -0.00313 -0.05177 F3B 5 0.945630 -0.065239 0.361079 -21.00000 0.14156 0.04433 = 0.06181 -0.00212 -0.05841 0.02711 PART 0 H1 2 0.585500 0.192483 -0.085069 11.00000 0.03001 H2 2 0.453717 0.469664 0.171338 11.00000 0.02983 H3 2 0.290888 0.550200 0.085104 11.00000 0.03420 H4 2 0.198162 0.432361 -0.105232 11.00000 0.02833 H5 2 0.268961 0.226730 -0.213432 11.00000 0.03680 H6 2 0.429177 0.143072 -0.129840 11.00000 0.02450 H8 2 0.749056 0.195323 0.218642 11.00000 0.02629 H10 2 0.949910 -0.080212 0.083725 11.00000 0.02778 H11 2 0.846327 -0.098578 -0.125964 11.00000 0.03432 H12 2 0.688745 0.022411 -0.161479 11.00000 0.02590 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.45574(8) 0.29566(13) 0.02816(11) 0.0177(2) Uani 1 1 d . . . C2 C 0.41408(9) 0.41609(14) 0.09126(12) 0.0208(2) Uani 1 1 d . . . C3 C 0.31933(9) 0.46521(15) 0.04127(13) 0.0236(3) Uani 1 1 d . . . C4 C 0.26570(9) 0.39519(16) -0.07200(13) 0.0250(3) Uani 1 1 d . . . C5 C 0.30691(10) 0.27623(15) -0.13579(13) 0.0248(3) Uani 1 1 d . . . C6 C 0.40142(9) 0.22645(14) -0.08588(12) 0.0206(2) Uani 1 1 d . . . C7 C 0.70506(8) 0.11778(13) 0.02721(11) 0.0183(2) Uani 1 1 d . . . C8 C 0.76810(9) 0.13506(14) 0.15026(12) 0.0204(2) Uani 1 1 d . . . C9 C 0.85874(9) 0.06097(15) 0.16855(12) 0.0225(2) Uani 1 1 d . A . C10 C 0.88864(10) -0.02592(16) 0.06798(14) 0.0263(3) Uani 1 1 d . . . C11 C 0.82654(10) -0.03824(16) -0.05537(14) 0.0265(3) Uani 1 1 d . . . C12 C 0.73528(9) 0.03247(15) -0.07567(12) 0.0230(2) Uani 1 1 d . . . C13 C 0.55640(9) 0.24214(13) 0.08807(11) 0.0181(2) Uani 1 1 d . . . C14 C 0.92508(10) 0.07019(18) 0.30275(14) 0.0305(3) Uani 1 1 d . . . N1 N 0.61002(7) 0.18303(12) -0.00052(10) 0.0186(2) Uani 1 1 d . . . O1 O 0.58706(7) 0.25080(11) 0.21015(8) 0.0248(2) Uani 1 1 d . . . F1A F 1.0177(4) 0.0860(13) 0.2959(7) 0.0669(17) Uani 0.57(3) 1 d P A 1 F2A F 0.9165(4) -0.0580(8) 0.3743(6) 0.0514(13) Uani 0.57(3) 1 d P A 1 F3A F 0.9038(6) 0.1836(11) 0.3803(7) 0.0689(18) Uani 0.57(3) 1 d P A 1 F1B F 0.8941(6) 0.1640(13) 0.3885(6) 0.0504(19) Uani 0.43(3) 1 d P A 2 F2B F 1.0126(7) 0.123(2) 0.2876(12) 0.089(4) Uani 0.43(3) 1 d P A 2 F3B F 0.9456(17) -0.0652(10) 0.3611(12) 0.092(3) Uani 0.43(3) 1 d P A 2 H1 H 0.5855(12) 0.192(2) -0.0851(18) 0.030(4) Uiso 1 1 d . . . H2 H 0.4537(12) 0.470(2) 0.1713(17) 0.030(4) Uiso 1 1 d . . . H3 H 0.2909(13) 0.550(2) 0.0851(18) 0.034(4) Uiso 1 1 d . . . H4 H 0.1982(12) 0.4324(19) -0.1052(16) 0.028(4) Uiso 1 1 d . . . H5 H 0.2690(13) 0.227(2) -0.2134(18) 0.037(5) Uiso 1 1 d . . . H6 H 0.4292(11) 0.1431(18) -0.1298(16) 0.024(4) Uiso 1 1 d . . . H8 H 0.7491(12) 0.1953(19) 0.2186(16) 0.026(4) Uiso 1 1 d . . . H10 H 0.9499(12) -0.0802(19) 0.0837(17) 0.028(4) Uiso 1 1 d . . . H11 H 0.8463(12) -0.099(2) -0.1260(17) 0.034(4) Uiso 1 1 d . . . H12 H 0.6887(12) 0.0224(19) -0.1615(16) 0.026(4) 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 C1 0.0189(5) 0.0196(5) 0.0152(5) 0.0024(4) 0.0043(4) -0.0005(4) C2 0.0237(6) 0.0225(5) 0.0172(5) 0.0007(4) 0.0061(4) -0.0006(4) C3 0.0239(6) 0.0239(6) 0.0251(6) 0.0027(5) 0.0096(5) 0.0029(5) C4 0.0187(6) 0.0289(6) 0.0272(6) 0.0065(5) 0.0032(5) 0.0019(5) C5 0.0222(6) 0.0275(6) 0.0230(6) 0.0002(5) -0.0007(5) -0.0024(5) C6 0.0217(6) 0.0208(5) 0.0191(5) -0.0010(4) 0.0027(4) -0.0011(4) C7 0.0184(5) 0.0203(5) 0.0167(5) 0.0025(4) 0.0041(4) 0.0006(4) C8 0.0205(6) 0.0236(5) 0.0173(5) -0.0003(4) 0.0038(4) -0.0014(4) C9 0.0175(5) 0.0283(6) 0.0209(6) 0.0026(4) 0.0015(4) -0.0015(4) C10 0.0193(6) 0.0320(7) 0.0279(6) 0.0033(5) 0.0054(5) 0.0040(5) C11 0.0273(6) 0.0314(6) 0.0228(6) -0.0012(5) 0.0095(5) 0.0056(5) C12 0.0250(6) 0.0275(6) 0.0170(5) 0.0007(4) 0.0050(4) 0.0022(5) C13 0.0202(5) 0.0197(5) 0.0147(5) 0.0013(4) 0.0037(4) -0.0005(4) C14 0.0198(6) 0.0423(8) 0.0277(7) -0.0021(6) -0.0002(5) 0.0025(5) N1 0.0195(5) 0.0235(5) 0.0124(4) 0.0011(3) 0.0018(3) 0.0027(4) O1 0.0234(4) 0.0379(5) 0.0128(4) -0.0016(3) 0.0023(3) 0.0029(4) F1A 0.0121(15) 0.154(5) 0.0338(18) 0.005(2) 0.0012(11) 0.005(2) F2A 0.055(2) 0.066(3) 0.0261(14) 0.0200(14) -0.0117(13) -0.012(2) F3A 0.061(3) 0.065(2) 0.066(3) -0.038(2) -0.030(2) 0.021(2) F1B 0.023(2) 0.107(6) 0.017(2) -0.019(2) -0.0062(14) 0.020(2) F2B 0.036(4) 0.170(8) 0.056(4) -0.027(4) -0.003(3) -0.052(5) F3B 0.142(8) 0.044(3) 0.062(4) -0.002(2) -0.058(4) 0.027(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C6 1.3933(16) . ? C1 C2 1.3938(16) . ? C1 C13 1.4915(16) . ? C2 C3 1.3863(18) . ? C2 H2 1.006(17) . ? C3 C4 1.3869(19) . ? C3 H3 0.973(18) . ? C4 C5 1.3851(19) . ? C4 H4 0.990(17) . ? C5 C6 1.3851(18) . ? C5 H5 0.963(18) . ? C6 H6 0.959(16) . ? C7 C8 1.3948(16) . ? C7 C12 1.3950(17) . ? C7 N1 1.4129(15) . ? C8 C9 1.3910(17) . ? C8 H8 0.938(16) . ? C9 C10 1.3818(18) . ? C9 C14 1.4992(18) . ? C10 C11 1.3872(19) . ? C10 H10 0.957(16) . ? C11 C12 1.3850(18) . ? C11 H11 0.960(18) . ? C12 H12 0.988(16) . ? C13 O1 1.2329(13) . ? C13 N1 1.3578(15) . ? C14 F1A 1.304(6) . ? C14 F1B 1.310(7) . ? C14 F3B 1.315(9) . ? C14 F3A 1.317(6) . ? C14 F2B 1.329(10) . ? C14 F2A 1.336(6) . ? N1 H1 0.865(17) . ? 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 C6 C1 C2 119.28(11) . . ? C6 C1 C13 122.21(11) . . ? C2 C1 C13 118.48(10) . . ? C3 C2 C1 120.12(11) . . ? C3 C2 H2 120.0(9) . . ? C1 C2 H2 119.8(9) . . ? C2 C3 C4 120.18(12) . . ? C2 C3 H3 119.8(10) . . ? C4 C3 H3 120.0(10) . . ? C5 C4 C3 120.00(12) . . ? C5 C4 H4 121.6(10) . . ? C3 C4 H4 118.4(10) . . ? C6 C5 C4 119.99(12) . . ? C6 C5 H5 120.3(11) . . ? C4 C5 H5 119.7(11) . . ? C5 C6 C1 120.42(12) . . ? C5 C6 H6 119.6(9) . . ? C1 C6 H6 120.0(9) . . ? C8 C7 C12 119.76(11) . . ? C8 C7 N1 123.31(11) . . ? C12 C7 N1 116.93(10) . . ? C9 C8 C7 118.56(11) . . ? C9 C8 H8 121.3(10) . . ? C7 C8 H8 120.1(10) . . ? C10 C9 C8 122.05(11) . . ? C10 C9 C14 118.51(11) . . ? C8 C9 C14 119.39(11) . . ? C9 C10 C11 118.84(12) . . ? C9 C10 H10 120.9(10) . . ? C11 C10 H10 120.2(10) . . ? C12 C11 C10 120.30(12) . . ? C12 C11 H11 120.0(10) . . ? C10 C11 H11 119.7(10) . . ? C11 C12 C7 120.44(12) . . ? C11 C12 H12 121.9(9) . . ? C7 C12 H12 117.6(9) . . ? O1 C13 N1 123.30(11) . . ? O1 C13 C1 121.29(10) . . ? N1 C13 C1 115.41(10) . . ? F1A C14 F1B 114.3(5) . . ? F1A C14 F3B 88.8(10) . . ? F1B C14 F3B 108.7(8) . . ? F1A C14 F3A 106.2(5) . . ? F3B C14 F3A 116.4(7) . . ? F1B C14 F2B 106.0(7) . . ? F3B C14 F2B 103.1(8) . . ? F3A C14 F2B 96.7(7) . . ? F1A C14 F2A 107.2(5) . . ? F1B C14 F2A 94.7(5) . . ? F3A C14 F2A 103.9(5) . . ? F2B C14 F2A 121.0(8) . . ? F1A C14 C9 114.2(3) . . ? F1B C14 C9 114.2(3) . . ? F3B C14 C9 114.1(5) . . ? F3A C14 C9 114.3(3) . . ? F2B C14 C9 109.9(5) . . ? F2A C14 C9 110.3(3) . . ? C13 N1 C7 128.07(10) . . ? C13 N1 H1 116.7(11) . . ? C7 N1 H1 115.0(11) . . ? 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 C6 C1 C2 C3 0.49(17) . . . . ? C13 C1 C2 C3 -177.69(11) . . . . ? C1 C2 C3 C4 -0.24(18) . . . . ? C2 C3 C4 C5 -0.24(19) . . . . ? C3 C4 C5 C6 0.5(2) . . . . ? C4 C5 C6 C1 -0.21(19) . . . . ? C2 C1 C6 C5 -0.26(18) . . . . ? C13 C1 C6 C5 177.85(11) . . . . ? C12 C7 C8 C9 -2.42(18) . . . . ? N1 C7 C8 C9 177.60(11) . . . . ? C7 C8 C9 C10 1.37(19) . . . . ? C7 C8 C9 C14 -176.37(12) . . . . ? C8 C9 C10 C11 0.6(2) . . . . ? C14 C9 C10 C11 178.37(13) . . . . ? C9 C10 C11 C12 -1.5(2) . . . . ? C10 C11 C12 C7 0.5(2) . . . . ? C8 C7 C12 C11 1.53(19) . . . . ? N1 C7 C12 C11 -178.49(11) . . . . ? C6 C1 C13 O1 -148.37(12) . . . . ? C2 C1 C13 O1 29.75(17) . . . . ? C6 C1 C13 N1 31.02(16) . . . . ? C2 C1 C13 N1 -150.85(11) . . . . ? C10 C9 C14 F1A 41.2(6) . . . . ? C8 C9 C14 F1A -141.0(6) . . . . ? C10 C9 C14 F1B 175.3(6) . . . . ? C8 C9 C14 F1B -6.9(6) . . . . ? C10 C9 C14 F3B -58.9(12) . . . . ? C8 C9 C14 F3B 119.0(12) . . . . ? C10 C9 C14 F3A 163.8(5) . . . . ? C8 C9 C14 F3A -18.4(6) . . . . ? C10 C9 C14 F2B 56.3(9) . . . . ? C8 C9 C14 F2B -125.9(9) . . . . ? C10 C9 C14 F2A -79.6(3) . . . . ? C8 C9 C14 F2A 98.2(3) . . . . ? O1 C13 N1 C7 2.38(19) . . . . ? C1 C13 N1 C7 -177.01(11) . . . . ? C8 C7 N1 C13 -14.74(19) . . . . ? C12 C7 N1 C13 165.28(12) . . . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.329 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.062 # Attachment 't-2-1.cif' data_T-2-1 _database_code_depnum_ccdc_archive 'CCDC 826197' #TrackingRef 't-2-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H9 F6 N O' _chemical_formula_sum 'C15 H9 F6 N O' _chemical_formula_weight 333.23 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 9.034(5) _cell_length_b 13.743(5) _cell_length_c 11.372(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1411.9(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 777 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.9 _exptl_crystal_description needles _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.568 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9221 _exptl_absorpt_correction_T_max 0.9756 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22894 _diffrn_reflns_av_R_equivalents 0.0339 _diffrn_reflns_av_sigmaI/netI 0.0293 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.70 _diffrn_reflns_theta_max 32.85 _reflns_number_total 4880 _reflns_number_gt 4062 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 4880 _refine_ls_number_parameters 244 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0502 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1047 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-2-1 in P n a 21 CELL 0.71073 9.034 13.743 11.372 90.000 90.000 90.000 ZERR 4 0.005 0.005 0.005 0.005 0.005 0.005 LATT -1 SYMM -X,-Y, 0.50000+Z SYMM 0.50000-X, 0.50000+Y, 0.50000+Z SYMM 0.50000+X, 0.50000-Y,Z SFAC C H N O F UNIT 60 36 4 4 24 MERG 2 L.S. 12 TEMP -153 FMAP 2 PLAN 15 ACTA 50 CONF BOND $H HTAB WGHT 0.064700 FVAR 8.68612 C1 1 0.039380 0.624183 0.203221 11.00000 0.01428 0.01919 = 0.02399 0.00262 -0.00433 -0.00125 C2 1 0.139231 0.558777 0.154150 11.00000 0.01838 0.02511 = 0.03656 0.00418 -0.00148 0.00170 C3 1 0.212571 0.491964 0.226121 11.00000 0.02079 0.02487 = 0.06418 0.01082 -0.00625 0.00394 C4 1 0.186075 0.490440 0.345264 11.00000 0.03169 0.03429 = 0.05955 0.02298 -0.02455 -0.00855 C5 1 0.090867 0.557161 0.395484 11.00000 0.04507 0.04117 = 0.02914 0.01266 -0.01781 -0.01904 C6 1 0.017079 0.624766 0.325172 11.00000 0.02742 0.02622 = 0.02514 0.00058 -0.00374 -0.00768 C7 1 -0.034830 0.827585 -0.009754 11.00000 0.01647 0.02288 = 0.02701 0.00760 0.00046 0.00106 C8 1 -0.121089 0.798524 -0.104846 11.00000 0.02326 0.02277 = 0.02579 0.00357 -0.00282 0.00488 C9 1 -0.179704 0.869243 -0.178877 11.00000 0.02489 0.02927 = 0.02281 0.00410 0.00093 0.00914 C10 1 -0.151718 0.968029 -0.159606 11.00000 0.02975 0.02644 = 0.02784 0.01039 0.00540 0.00667 C11 1 -0.064218 0.995783 -0.065230 11.00000 0.02889 0.02168 = 0.03879 0.00825 0.00462 0.00018 C12 1 -0.005716 0.925789 0.010069 11.00000 0.01935 0.02496 = 0.03291 0.00558 -0.00021 -0.00353 C13 1 -0.048914 0.687829 0.121987 11.00000 0.01551 0.02003 = 0.02385 0.00260 -0.00200 0.00131 C14 1 -0.271138 0.840791 -0.282264 11.00000 0.04116 0.03584 = 0.02526 0.00076 -0.00821 0.01595 C15 1 -0.079133 0.699782 0.383028 11.00000 0.04661 0.03800 = 0.03531 -0.01051 0.01004 -0.01132 N1 3 0.029029 0.757313 0.066745 11.00000 0.01560 0.02324 = 0.03044 0.00818 -0.00702 -0.00231 O1 4 -0.181805 0.672847 0.107618 11.00000 0.01478 0.02898 = 0.04130 0.01043 -0.00673 -0.00165 F1 5 -0.210991 0.871796 -0.383635 11.00000 0.08466 0.09112 = 0.02269 0.00780 -0.00203 0.00275 F2 5 -0.407092 0.878116 -0.279182 11.00000 0.04574 0.08756 = 0.05741 -0.03039 -0.02352 0.03342 F3 5 -0.287288 0.745291 -0.294450 11.00000 0.09959 0.03893 = 0.05121 -0.00581 -0.04195 0.01087 F4 5 -0.222457 0.676883 0.382614 11.00000 0.04843 0.04928 = 0.12909 -0.03313 0.04286 -0.01793 F5 5 -0.072910 0.786771 0.328588 11.00000 0.05522 0.02924 = 0.05899 -0.01244 0.01207 -0.00202 F6 5 -0.037265 0.717727 0.492953 11.00000 0.13430 0.09329 = 0.03135 -0.02331 0.00040 0.01654 H1 2 0.119818 0.766111 0.095711 11.00000 0.03120 H2 2 0.155579 0.561536 0.068814 11.00000 0.04142 H3 2 0.277760 0.449900 0.196038 11.00000 0.05515 H4 2 0.225601 0.447746 0.396678 11.00000 0.05479 H5 2 0.066998 0.562100 0.481782 11.00000 0.05643 H8 2 -0.147597 0.732319 -0.114591 11.00000 0.01709 H10 2 -0.191743 1.018955 -0.214268 11.00000 0.03794 H11 2 -0.038256 1.062937 -0.048973 11.00000 0.03450 H12 2 0.061976 0.941210 0.068653 11.00000 0.03600 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.03938(12) 0.62418(8) 0.20322(11) 0.0192(2) Uani 1 1 d . . . C2 C 0.13923(14) 0.55878(10) 0.15415(14) 0.0267(3) Uani 1 1 d . . . C3 C 0.21257(15) 0.49196(11) 0.22612(19) 0.0366(4) Uani 1 1 d . . . C4 C 0.18608(17) 0.49044(12) 0.34526(18) 0.0418(4) Uani 1 1 d . . . C5 C 0.09087(19) 0.55716(12) 0.39548(16) 0.0385(4) Uani 1 1 d . . . C6 C 0.01708(15) 0.62477(9) 0.32517(13) 0.0263(3) Uani 1 1 d . . . C7 C -0.03483(13) 0.82759(9) -0.00975(12) 0.0221(2) Uani 1 1 d . . . C8 C -0.12109(14) 0.79852(9) -0.10485(12) 0.0239(2) Uani 1 1 d . . . C9 C -0.17970(15) 0.86924(10) -0.17888(13) 0.0257(2) Uani 1 1 d . . . C10 C -0.15172(15) 0.96803(10) -0.15961(13) 0.0280(3) Uani 1 1 d . . . C11 C -0.06422(16) 0.99578(10) -0.06523(15) 0.0298(3) Uani 1 1 d . . . C12 C -0.00572(15) 0.92579(9) 0.01007(14) 0.0257(3) Uani 1 1 d . . . C13 C -0.04891(13) 0.68783(9) 0.12199(12) 0.0198(2) Uani 1 1 d . . . C14 C -0.27114(18) 0.84079(11) -0.28226(14) 0.0341(3) Uani 1 1 d . . . C15 C -0.0791(2) 0.69978(12) 0.38303(16) 0.0400(4) Uani 1 1 d . . . N1 N 0.02903(12) 0.75731(8) 0.06675(11) 0.0231(2) Uani 1 1 d . . . O1 O -0.18181(10) 0.67285(7) 0.10762(10) 0.0284(2) Uani 1 1 d . . . F1 F -0.21099(18) 0.87180(11) -0.38364(10) 0.0662(4) Uani 1 1 d . . . F2 F -0.40709(13) 0.87812(10) -0.27918(12) 0.0636(4) Uani 1 1 d . . . F3 F -0.28729(17) 0.74529(8) -0.29445(12) 0.0632(4) Uani 1 1 d . . . F4 F -0.22246(13) 0.67688(9) 0.38261(17) 0.0756(5) Uani 1 1 d . . . F5 F -0.07291(13) 0.78677(7) 0.32859(12) 0.0478(3) Uani 1 1 d . . . F6 F -0.0373(2) 0.71773(13) 0.49295(12) 0.0863(5) Uani 1 1 d . . . H1 H 0.120(2) 0.7661(13) 0.0957(19) 0.031(5) Uiso 1 1 d . . . H2 H 0.156(2) 0.5615(16) 0.069(2) 0.041(6) Uiso 1 1 d . . . H3 H 0.278(3) 0.4499(17) 0.196(2) 0.055(7) Uiso 1 1 d . . . H4 H 0.226(3) 0.4477(16) 0.397(2) 0.055(6) Uiso 1 1 d . . . H5 H 0.067(3) 0.5621(18) 0.482(3) 0.056(7) Uiso 1 1 d . . . H8 H -0.1476(17) 0.7323(12) -0.1146(16) 0.017(4) Uiso 1 1 d . . . H10 H -0.192(2) 1.0190(14) -0.2143(19) 0.038(5) Uiso 1 1 d . . . H11 H -0.038(2) 1.0629(15) -0.049(2) 0.034(5) Uiso 1 1 d . . . H12 H 0.062(2) 0.9412(14) 0.069(2) 0.036(5) 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 C1 0.0143(4) 0.0192(5) 0.0240(6) 0.0026(4) -0.0043(4) -0.0012(4) C2 0.0184(5) 0.0251(6) 0.0366(8) 0.0042(5) -0.0015(5) 0.0017(4) C3 0.0208(6) 0.0249(6) 0.0642(11) 0.0108(7) -0.0062(7) 0.0039(5) C4 0.0317(7) 0.0343(8) 0.0596(11) 0.0230(7) -0.0246(8) -0.0085(6) C5 0.0451(9) 0.0412(8) 0.0291(7) 0.0127(6) -0.0178(7) -0.0190(6) C6 0.0274(6) 0.0262(6) 0.0251(6) 0.0006(5) -0.0037(5) -0.0077(5) C7 0.0165(5) 0.0229(6) 0.0270(6) 0.0076(5) 0.0005(5) 0.0011(4) C8 0.0233(5) 0.0228(6) 0.0258(6) 0.0036(5) -0.0028(5) 0.0049(4) C9 0.0249(6) 0.0293(6) 0.0228(6) 0.0041(5) 0.0009(5) 0.0091(5) C10 0.0298(6) 0.0264(6) 0.0278(7) 0.0104(5) 0.0054(5) 0.0067(5) C11 0.0289(6) 0.0217(6) 0.0388(8) 0.0083(5) 0.0046(6) 0.0002(5) C12 0.0194(5) 0.0250(6) 0.0329(7) 0.0056(5) -0.0002(5) -0.0035(4) C13 0.0155(5) 0.0200(5) 0.0238(6) 0.0026(5) -0.0020(4) 0.0013(4) C14 0.0412(8) 0.0358(7) 0.0253(6) 0.0008(6) -0.0082(6) 0.0160(6) C15 0.0466(9) 0.0380(8) 0.0353(8) -0.0105(7) 0.0100(7) -0.0113(7) N1 0.0156(5) 0.0232(5) 0.0304(6) 0.0082(4) -0.0070(4) -0.0023(4) O1 0.0148(4) 0.0290(4) 0.0413(6) 0.0104(4) -0.0067(4) -0.0016(3) F1 0.0847(10) 0.0911(9) 0.0227(5) 0.0078(6) -0.0020(6) 0.0028(7) F2 0.0457(6) 0.0876(9) 0.0574(7) -0.0304(7) -0.0235(6) 0.0334(6) F3 0.0996(11) 0.0389(6) 0.0512(7) -0.0058(5) -0.0420(7) 0.0109(6) F4 0.0484(6) 0.0493(6) 0.1291(14) -0.0331(7) 0.0429(8) -0.0179(5) F5 0.0552(6) 0.0292(4) 0.0590(7) -0.0124(5) 0.0121(5) -0.0020(4) F6 0.1343(15) 0.0933(11) 0.0313(6) -0.0233(7) 0.0004(8) 0.0165(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C2 1.3904(19) . ? C1 C6 1.401(2) . ? C1 C13 1.5016(17) . ? C2 C3 1.397(2) . ? C2 H2 0.98(2) . ? C3 C4 1.376(3) . ? C3 H3 0.89(2) . ? C4 C5 1.381(3) . ? C4 H4 0.90(3) . ? C5 C6 1.395(2) . ? C5 H5 1.01(3) . ? C6 C15 1.500(2) . ? C7 C8 1.391(2) . ? C7 C12 1.3934(19) . ? C7 N1 1.4221(16) . ? C8 C9 1.3906(18) . ? C8 H8 0.947(16) . ? C9 C10 1.398(2) . ? C9 C14 1.489(2) . ? C10 C11 1.386(2) . ? C10 H10 1.00(2) . ? C11 C12 1.392(2) . ? C11 H11 0.97(2) . ? C12 H12 0.93(2) . ? C13 O1 1.2290(16) . ? C13 N1 1.3425(16) . ? C14 F3 1.3278(19) . ? C14 F2 1.3315(19) . ? C14 F1 1.344(2) . ? C15 F6 1.329(2) . ? C15 F4 1.332(2) . ? C15 F5 1.347(2) . ? N1 H1 0.89(2) . ? 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 C2 C1 C6 119.61(12) . . ? C2 C1 C13 118.32(12) . . ? C6 C1 C13 121.95(12) . . ? C1 C2 C3 119.83(15) . . ? C1 C2 H2 118.0(13) . . ? C3 C2 H2 122.2(13) . . ? C4 C3 C2 120.29(16) . . ? C4 C3 H3 118.8(16) . . ? C2 C3 H3 120.9(17) . . ? C3 C4 C5 120.36(14) . . ? C3 C4 H4 125.4(16) . . ? C5 C4 H4 114.2(16) . . ? C4 C5 C6 120.18(16) . . ? C4 C5 H5 125.5(14) . . ? C6 C5 H5 114.3(15) . . ? C5 C6 C1 119.64(15) . . ? C5 C6 C15 118.88(16) . . ? C1 C6 C15 121.41(13) . . ? C8 C7 C12 120.63(12) . . ? C8 C7 N1 120.51(12) . . ? C12 C7 N1 118.83(12) . . ? C9 C8 C7 118.89(13) . . ? C9 C8 H8 120.3(10) . . ? C7 C8 H8 120.5(10) . . ? C8 C9 C10 120.99(14) . . ? C8 C9 C14 120.38(13) . . ? C10 C9 C14 118.62(12) . . ? C11 C10 C9 119.44(12) . . ? C11 C10 H10 119.5(12) . . ? C9 C10 H10 121.0(12) . . ? C10 C11 C12 120.17(13) . . ? C10 C11 H11 123.2(13) . . ? C12 C11 H11 116.6(13) . . ? C11 C12 C7 119.88(14) . . ? C11 C12 H12 122.2(13) . . ? C7 C12 H12 117.5(12) . . ? O1 C13 N1 124.70(12) . . ? O1 C13 C1 120.21(11) . . ? N1 C13 C1 115.06(11) . . ? F3 C14 F2 106.39(15) . . ? F3 C14 F1 105.57(14) . . ? F2 C14 F1 105.87(14) . . ? F3 C14 C9 113.76(12) . . ? F2 C14 C9 112.94(13) . . ? F1 C14 C9 111.70(14) . . ? F6 C15 F4 108.89(17) . . ? F6 C15 F5 104.81(15) . . ? F4 C15 F5 104.39(16) . . ? F6 C15 C6 112.03(17) . . ? F4 C15 C6 113.52(13) . . ? F5 C15 C6 112.58(14) . . ? C13 N1 C7 123.82(11) . . ? C13 N1 H1 113.9(12) . . ? C7 N1 H1 120.5(12) . . ? 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 C6 C1 C2 C3 2.24(19) . . . . ? C13 C1 C2 C3 -173.78(12) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C2 C3 C4 C5 -2.3(2) . . . . ? C3 C4 C5 C6 2.0(2) . . . . ? C4 C5 C6 C1 0.4(2) . . . . ? C4 C5 C6 C15 -176.68(13) . . . . ? C2 C1 C6 C5 -2.53(19) . . . . ? C13 C1 C6 C5 173.33(12) . . . . ? C2 C1 C6 C15 174.48(12) . . . . ? C13 C1 C6 C15 -9.65(19) . . . . ? C12 C7 C8 C9 -0.95(19) . . . . ? N1 C7 C8 C9 -178.95(12) . . . . ? C7 C8 C9 C10 0.7(2) . . . . ? C7 C8 C9 C14 179.32(13) . . . . ? C8 C9 C10 C11 0.0(2) . . . . ? C14 C9 C10 C11 -178.64(13) . . . . ? C9 C10 C11 C12 -0.5(2) . . . . ? C10 C11 C12 C7 0.2(2) . . . . ? C8 C7 C12 C11 0.5(2) . . . . ? N1 C7 C12 C11 178.53(12) . . . . ? C2 C1 C13 O1 107.87(15) . . . . ? C6 C1 C13 O1 -68.05(18) . . . . ? C2 C1 C13 N1 -70.27(15) . . . . ? C6 C1 C13 N1 113.81(14) . . . . ? C8 C9 C14 F3 -0.5(2) . . . . ? C10 C9 C14 F3 178.09(15) . . . . ? C8 C9 C14 F2 120.86(16) . . . . ? C10 C9 C14 F2 -60.5(2) . . . . ? C8 C9 C14 F1 -119.94(16) . . . . ? C10 C9 C14 F1 58.70(17) . . . . ? C5 C6 C15 F6 25.5(2) . . . . ? C1 C6 C15 F6 -151.52(15) . . . . ? C5 C6 C15 F4 -98.32(19) . . . . ? C1 C6 C15 F4 84.64(19) . . . . ? C5 C6 C15 F5 143.35(15) . . . . ? C1 C6 C15 F5 -33.69(19) . . . . ? O1 C13 N1 C7 4.8(2) . . . . ? C1 C13 N1 C7 -177.19(12) . . . . ? C8 C7 N1 C13 -54.39(18) . . . . ? C12 C7 N1 C13 127.58(14) . . . . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.243 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.049 # Attachment 't-2-2.cif' data_T-2-2 _database_code_depnum_ccdc_archive 'CCDC 826198' #TrackingRef 't-2-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H9 F6 N O' _chemical_formula_sum 'C15 H9 F6 N O' _chemical_formula_weight 333.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 21/c' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.059(5) _cell_length_b 12.540(5) _cell_length_c 8.884(5) _cell_angle_alpha 90 _cell_angle_beta 91.804(5) _cell_angle_gamma 90 _cell_volume 1342.8(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 947 _cell_measurement_theta_min 1.9 _cell_measurement_theta_max 25.5 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.648 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.161 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9235 _exptl_absorpt_correction_T_max 0.9765 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22116 _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0636 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 32.76 _reflns_number_total 4633 _reflns_number_gt 2814 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4633 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1001 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1371 _refine_ls_wR_factor_gt 0.1244 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-2-2 in P 1 21/c 1 CELL 0.71073 12.059 12.540 8.884 90.000 91.804 90.000 ZERR 4 0.005 0.005 0.005 0.005 0.005 0.005 LATT 1 SYMM -X, 0.50000+Y, 0.50000-Z SFAC C H N O F UNIT 60 36 4 4 24 MERG 2 L.S. 12 TEMP -153 ACTA 50 CONF BOND $H HTAB FMAP 2 PLAN 15 WGHT 0.067000 FVAR 3.72122 C1 1 0.199570 0.382088 0.510486 11.00000 0.01692 0.01840 = 0.01617 -0.00402 0.00038 0.00162 C2 1 0.212786 0.491189 0.490660 11.00000 0.02145 0.02323 = 0.02018 0.00059 0.00358 -0.00036 C3 1 0.156256 0.562829 0.578647 11.00000 0.02913 0.01523 = 0.02769 0.00126 0.00751 -0.00092 C4 1 0.084034 0.526424 0.685530 11.00000 0.02449 0.01731 = 0.02372 -0.00372 0.00667 0.00281 C5 1 0.068803 0.417489 0.703481 11.00000 0.01668 0.01676 = 0.01772 -0.00063 0.00162 -0.00051 C6 1 0.126454 0.344904 0.617272 11.00000 0.01874 0.01391 = 0.01901 -0.00324 0.00021 -0.00013 C7 1 0.341561 0.124788 0.402986 11.00000 0.01569 0.01697 = 0.01627 -0.00250 0.00123 0.00105 C8 1 0.413354 0.134271 0.283368 11.00000 0.01871 0.01935 = 0.01920 0.00235 0.00204 0.00016 C9 1 0.462619 0.043566 0.225561 11.00000 0.02108 0.02647 = 0.01903 -0.00034 0.00854 0.00133 C10 1 0.441363 -0.056738 0.284793 11.00000 0.02068 0.01906 = 0.02228 -0.00399 0.00591 0.00396 C11 1 0.370081 -0.065041 0.403360 11.00000 0.01841 0.01617 = 0.01761 -0.00127 0.00121 0.00055 C12 1 0.320860 0.024903 0.462886 11.00000 0.01747 0.02028 = 0.01683 -0.00296 0.00531 -0.00018 C13 1 0.263299 0.308585 0.411441 11.00000 0.01875 0.01878 = 0.01653 -0.00077 0.00133 -0.00117 C14 1 0.340355 -0.172043 0.464581 11.00000 0.02662 0.01971 = 0.02420 -0.00173 0.00445 -0.00012 C15 1 -0.008803 0.378902 0.819550 11.00000 0.02573 0.01807 = 0.02630 -0.00165 0.00866 0.00107 N1 3 0.289522 0.212969 0.472711 11.00000 0.02408 0.01925 = 0.01368 0.00048 0.00581 0.00153 O1 4 0.288450 0.335798 0.283688 11.00000 0.03672 0.02339 = 0.01352 0.00186 0.00746 -0.00005 F1 5 0.420538 -0.245335 0.446314 11.00000 0.05275 0.02036 = 0.04884 0.00627 0.02247 0.01256 F2 5 0.248249 -0.211683 0.396429 11.00000 0.04951 0.03493 = 0.04492 0.00791 -0.01247 -0.02277 F3 5 0.320635 -0.171062 0.612086 11.00000 0.04112 0.02629 = 0.02435 0.00470 0.01047 -0.00004 F4 5 -0.039334 0.277946 0.798245 11.00000 0.09321 0.03160 = 0.07999 -0.02144 0.06285 -0.03270 F5 5 -0.100699 0.437025 0.825679 11.00000 0.02383 0.05875 = 0.04085 0.01386 0.01450 0.01226 F6 5 0.037064 0.382954 0.959361 11.00000 0.03996 0.06167 = 0.02471 0.01530 0.00667 0.00974 H1 2 0.272604 0.208027 0.567912 11.00000 0.04074 H2 2 0.264094 0.517273 0.413166 11.00000 0.01572 H3 2 0.166677 0.634010 0.567530 11.00000 0.02219 H4 2 0.045532 0.576154 0.747993 11.00000 0.03108 H6 2 0.115339 0.268799 0.630041 11.00000 0.02248 H8 2 0.428658 0.202647 0.243013 11.00000 0.02358 H9 2 0.514562 0.051920 0.145324 11.00000 0.03212 H10 2 0.474510 -0.116410 0.247142 11.00000 0.03137 H12 2 0.274326 0.015409 0.543221 11.00000 0.01789 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.19957(13) 0.38209(13) 0.51049(17) 0.0172(3) Uani 1 1 d . . . C2 C 0.21279(14) 0.49119(14) 0.4907(2) 0.0216(4) Uani 1 1 d . . . C3 C 0.15626(15) 0.56283(15) 0.5786(2) 0.0239(4) Uani 1 1 d . . . C4 C 0.08403(15) 0.52642(14) 0.6855(2) 0.0217(4) Uani 1 1 d . . . C5 C 0.06880(13) 0.41749(13) 0.70348(18) 0.0170(3) Uani 1 1 d . . . C6 C 0.12645(13) 0.34490(13) 0.61727(18) 0.0172(3) Uani 1 1 d . . . C7 C 0.34156(12) 0.12479(13) 0.40299(17) 0.0163(3) Uani 1 1 d . . . C8 C 0.41335(13) 0.13427(14) 0.28337(18) 0.0191(3) Uani 1 1 d . . . C9 C 0.46262(14) 0.04357(14) 0.22556(19) 0.0220(4) Uani 1 1 d . . . C10 C 0.44136(14) -0.05674(14) 0.28479(19) 0.0206(3) Uani 1 1 d . . . C11 C 0.37008(13) -0.06504(13) 0.40336(18) 0.0174(3) Uani 1 1 d . . . C12 C 0.32086(14) 0.02490(13) 0.46289(19) 0.0181(3) Uani 1 1 d . . . C13 C 0.26330(13) 0.30859(14) 0.41144(18) 0.0180(3) Uani 1 1 d . . . C14 C 0.34035(15) -0.17204(14) 0.4646(2) 0.0234(4) Uani 1 1 d . . . C15 C -0.00880(14) 0.37890(14) 0.8196(2) 0.0232(4) Uani 1 1 d . . . N1 N 0.28952(12) 0.21297(11) 0.47271(16) 0.0189(3) Uani 1 1 d . . . O1 O 0.28845(11) 0.33580(10) 0.28369(13) 0.0244(3) Uani 1 1 d . . . F1 F 0.42054(11) -0.24534(9) 0.44631(14) 0.0402(3) Uani 1 1 d . . . F2 F 0.24825(11) -0.21168(10) 0.39643(14) 0.0434(3) Uani 1 1 d . . . F3 F 0.32064(9) -0.17106(8) 0.61209(12) 0.0304(3) Uani 1 1 d . . . F4 F -0.03933(14) 0.27795(10) 0.79824(18) 0.0670(5) Uani 1 1 d . . . F5 F -0.10070(9) 0.43703(11) 0.82568(14) 0.0409(3) Uani 1 1 d . . . F6 F 0.03706(10) 0.38295(11) 0.95936(13) 0.0420(3) Uani 1 1 d . . . H1 H 0.2726(19) 0.2080(18) 0.568(3) 0.041(6) Uiso 1 1 d . . . H2 H 0.2641(15) 0.5173(14) 0.413(2) 0.016(5) Uiso 1 1 d . . . H3 H 0.1667(15) 0.6340(17) 0.568(2) 0.022(5) Uiso 1 1 d . . . H4 H 0.0455(17) 0.5762(17) 0.748(2) 0.031(5) Uiso 1 1 d . . . H6 H 0.1153(16) 0.2688(16) 0.630(2) 0.022(5) Uiso 1 1 d . . . H8 H 0.4287(16) 0.2026(16) 0.243(2) 0.024(5) Uiso 1 1 d . . . H9 H 0.5146(18) 0.0519(16) 0.145(2) 0.032(5) Uiso 1 1 d . . . H10 H 0.4745(17) -0.1164(17) 0.247(2) 0.031(6) Uiso 1 1 d . . . H12 H 0.2743(16) 0.0154(15) 0.543(2) 0.018(5) 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 C1 0.0169(7) 0.0184(8) 0.0162(7) -0.0040(6) 0.0004(6) 0.0016(6) C2 0.0214(8) 0.0232(9) 0.0202(8) 0.0006(7) 0.0036(7) -0.0004(7) C3 0.0291(9) 0.0152(8) 0.0277(9) 0.0013(7) 0.0075(7) -0.0009(7) C4 0.0245(8) 0.0173(8) 0.0237(9) -0.0037(7) 0.0067(7) 0.0028(7) C5 0.0167(7) 0.0168(8) 0.0177(7) -0.0006(6) 0.0016(6) -0.0005(6) C6 0.0187(7) 0.0139(7) 0.0190(8) -0.0032(6) 0.0002(6) -0.0001(6) C7 0.0157(7) 0.0170(8) 0.0163(7) -0.0025(6) 0.0012(6) 0.0010(6) C8 0.0187(8) 0.0194(8) 0.0192(8) 0.0024(7) 0.0020(6) 0.0002(6) C9 0.0211(8) 0.0265(9) 0.0190(8) -0.0003(7) 0.0085(6) 0.0013(7) C10 0.0207(8) 0.0191(8) 0.0223(8) -0.0040(7) 0.0059(6) 0.0040(7) C11 0.0184(7) 0.0162(8) 0.0176(7) -0.0013(6) 0.0012(6) 0.0005(6) C12 0.0175(7) 0.0203(8) 0.0168(8) -0.0030(6) 0.0053(6) -0.0002(6) C13 0.0188(7) 0.0188(8) 0.0165(8) -0.0008(6) 0.0013(6) -0.0012(6) C14 0.0266(9) 0.0197(9) 0.0242(9) -0.0017(7) 0.0045(7) -0.0001(7) C15 0.0257(9) 0.0181(8) 0.0263(9) -0.0017(7) 0.0087(7) 0.0011(7) N1 0.0241(7) 0.0192(7) 0.0137(7) 0.0005(5) 0.0058(5) 0.0015(6) O1 0.0367(7) 0.0234(7) 0.0135(6) 0.0019(5) 0.0075(5) 0.0000(5) F1 0.0528(8) 0.0204(6) 0.0488(8) 0.0063(5) 0.0225(6) 0.0126(5) F2 0.0495(8) 0.0349(7) 0.0449(7) 0.0079(6) -0.0125(6) -0.0228(6) F3 0.0411(7) 0.0263(6) 0.0243(6) 0.0047(5) 0.0105(5) 0.0000(5) F4 0.0932(12) 0.0316(7) 0.0800(11) -0.0214(7) 0.0628(10) -0.0327(8) F5 0.0238(6) 0.0587(8) 0.0409(7) 0.0139(6) 0.0145(5) 0.0123(6) F6 0.0400(7) 0.0617(9) 0.0247(6) 0.0153(6) 0.0067(5) 0.0097(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C2 1.389(2) . ? C1 C6 1.396(2) . ? C1 C13 1.502(2) . ? C2 C3 1.384(3) . ? C2 H2 0.995(18) . ? C3 C4 1.386(2) . ? C3 H3 0.91(2) . ? C4 C5 1.388(2) . ? C4 H4 0.96(2) . ? C5 C6 1.390(2) . ? C5 C15 1.495(2) . ? C6 H6 0.97(2) . ? C7 C12 1.387(2) . ? C7 C8 1.397(2) . ? C7 N1 1.423(2) . ? C8 C9 1.389(2) . ? C8 H8 0.95(2) . ? C9 C10 1.390(3) . ? C9 H9 0.97(2) . ? C10 C11 1.384(2) . ? C10 H10 0.92(2) . ? C11 C12 1.387(2) . ? C11 C14 1.496(2) . ? C12 H12 0.93(2) . ? C13 O1 1.232(2) . ? C13 N1 1.350(2) . ? C14 F3 1.339(2) . ? C14 F2 1.343(2) . ? C14 F1 1.348(2) . ? C15 F5 1.329(2) . ? C15 F4 1.330(2) . ? C15 F6 1.345(2) . ? N1 H1 0.88(2) . ? 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 C2 C1 C6 119.52(15) . . ? C2 C1 C13 117.85(14) . . ? C6 C1 C13 122.61(15) . . ? C3 C2 C1 120.46(16) . . ? C3 C2 H2 120.3(11) . . ? C1 C2 H2 119.2(10) . . ? C2 C3 C4 120.29(17) . . ? C2 C3 H3 120.3(12) . . ? C4 C3 H3 119.4(12) . . ? C3 C4 C5 119.42(16) . . ? C3 C4 H4 120.4(12) . . ? C5 C4 H4 120.2(12) . . ? C4 C5 C6 120.72(15) . . ? C4 C5 C15 119.07(14) . . ? C6 C5 C15 120.20(15) . . ? C5 C6 C1 119.57(16) . . ? C5 C6 H6 120.4(11) . . ? C1 C6 H6 120.0(11) . . ? C12 C7 C8 119.49(15) . . ? C12 C7 N1 116.60(14) . . ? C8 C7 N1 123.88(15) . . ? C9 C8 C7 119.61(16) . . ? C9 C8 H8 120.6(12) . . ? C7 C8 H8 119.8(12) . . ? C8 C9 C10 120.98(16) . . ? C8 C9 H9 118.5(12) . . ? C10 C9 H9 120.5(12) . . ? C11 C10 C9 118.84(16) . . ? C11 C10 H10 120.3(13) . . ? C9 C10 H10 120.8(13) . . ? C10 C11 C12 120.82(16) . . ? C10 C11 C14 120.39(15) . . ? C12 C11 C14 118.72(15) . . ? C7 C12 C11 120.26(15) . . ? C7 C12 H12 122.1(11) . . ? C11 C12 H12 117.7(12) . . ? O1 C13 N1 123.78(15) . . ? O1 C13 C1 120.99(16) . . ? N1 C13 C1 115.24(14) . . ? F3 C14 F2 105.94(14) . . ? F3 C14 F1 105.92(14) . . ? F2 C14 F1 106.23(15) . . ? F3 C14 C11 113.55(14) . . ? F2 C14 C11 111.85(15) . . ? F1 C14 C11 112.77(14) . . ? F5 C15 F4 107.48(16) . . ? F5 C15 F6 105.11(14) . . ? F4 C15 F6 105.74(16) . . ? F5 C15 C5 113.06(15) . . ? F4 C15 C5 112.73(14) . . ? F6 C15 C5 112.13(15) . . ? C13 N1 C7 127.99(15) . . ? C13 N1 H1 113.1(15) . . ? C7 N1 H1 118.9(15) . . ? 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 C6 C1 C2 C3 1.7(3) . . . . ? C13 C1 C2 C3 -179.97(16) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? C3 C4 C5 C15 179.69(17) . . . . ? C4 C5 C6 C1 -0.7(2) . . . . ? C15 C5 C6 C1 -179.29(16) . . . . ? C2 C1 C6 C5 -0.7(2) . . . . ? C13 C1 C6 C5 -178.96(15) . . . . ? C12 C7 C8 C9 0.3(2) . . . . ? N1 C7 C8 C9 178.18(15) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C8 C9 C10 C11 -0.2(3) . . . . ? C9 C10 C11 C12 -0.3(3) . . . . ? C9 C10 C11 C14 176.67(16) . . . . ? C8 C7 C12 C11 -0.7(2) . . . . ? N1 C7 C12 C11 -178.76(15) . . . . ? C10 C11 C12 C7 0.7(3) . . . . ? C14 C11 C12 C7 -176.27(15) . . . . ? C2 C1 C13 O1 -29.1(2) . . . . ? C6 C1 C13 O1 149.21(17) . . . . ? C2 C1 C13 N1 151.09(16) . . . . ? C6 C1 C13 N1 -30.6(2) . . . . ? C10 C11 C14 F3 148.66(16) . . . . ? C12 C11 C14 F3 -34.3(2) . . . . ? C10 C11 C14 F2 -91.5(2) . . . . ? C12 C11 C14 F2 85.5(2) . . . . ? C10 C11 C14 F1 28.2(2) . . . . ? C12 C11 C14 F1 -154.83(16) . . . . ? C4 C5 C15 F5 40.5(2) . . . . ? C6 C5 C15 F5 -140.88(16) . . . . ? C4 C5 C15 F4 162.63(17) . . . . ? C6 C5 C15 F4 -18.7(2) . . . . ? C4 C5 C15 F6 -78.2(2) . . . . ? C6 C5 C15 F6 100.50(18) . . . . ? O1 C13 N1 C7 -5.0(3) . . . . ? C1 C13 N1 C7 174.88(15) . . . . ? C12 C7 N1 C13 -154.98(17) . . . . ? C8 C7 N1 C13 27.1(3) . . . . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.531 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.064 # Attachment 't-3-1.cif' data_T-3-1 _database_code_depnum_ccdc_archive 'CCDC 826199' #TrackingRef 't-3-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H9 F6 N O' _chemical_formula_sum 'C15 H9 F6 N O' _chemical_formula_weight 333.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 12.8346(8) _cell_length_b 8.061(5) _cell_length_c 14.155(5) _cell_angle_alpha 90 _cell_angle_beta 108.350(5) _cell_angle_gamma 90 _cell_volume 1390.0(11) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 719 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 25.7 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9189 _exptl_absorpt_correction_T_max 0.9678 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23224 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 32.81 _reflns_number_total 4769 _reflns_number_gt 2610 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4769 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0445 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1031 _refine_ls_goodness_of_fit_ref 0.976 _refine_ls_restrained_S_all 0.976 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-3-1 in P 1 21/n 1 CELL 0.71073 12.835 8.061 14.155 90.000 108.350 90.000 ZERR 4 0.005 0.005 0.005 0.005 0.005 0.005 LATT 1 SYMM 0.50000-X, 0.50000+Y, 0.50000-Z SFAC C H N O F UNIT 60 36 4 4 24 MERG 2 L.S. 12 TEMP -153 ACTA 50 HTAB BOND $H CONF FMAP 2 PLAN 15 WGHT 0.053600 FVAR 4.83063 0.42610 C1 1 0.751546 0.186013 0.357737 11.00000 0.03179 0.02884 = 0.01817 0.00318 0.00368 -0.00177 C2 1 0.683277 0.250494 0.408700 11.00000 0.03123 0.03340 = 0.02032 0.00287 0.00392 -0.00260 C3 1 0.722910 0.270920 0.511539 11.00000 0.04291 0.04186 = 0.02128 0.00058 0.00754 -0.00249 C4 1 0.830502 0.226101 0.563894 11.00000 0.04607 0.04591 = 0.01716 0.00291 -0.00061 -0.00387 C5 1 0.898577 0.165913 0.513620 11.00000 0.03294 0.04553 = 0.02646 0.00630 -0.00339 0.00062 C6 1 0.860075 0.146908 0.410782 11.00000 0.03118 0.03684 = 0.02593 0.00382 0.00363 0.00178 C7 1 0.731107 0.217936 0.085618 11.00000 0.02687 0.02614 = 0.01907 -0.00042 0.00569 0.00360 C8 1 0.639729 0.134127 0.024314 11.00000 0.03233 0.03831 = 0.02249 0.00142 0.00671 -0.00628 C9 1 0.615852 0.142699 -0.078162 11.00000 0.03459 0.03852 = 0.02070 -0.00136 0.00381 -0.00285 C10 1 0.682507 0.232298 -0.119687 11.00000 0.03812 0.03093 = 0.02148 -0.00220 0.01055 0.00261 C11 1 0.775566 0.311951 -0.058509 11.00000 0.03842 0.04003 = 0.02702 -0.00126 0.01577 -0.00524 C12 1 0.799789 0.303926 0.043994 11.00000 0.02927 0.03670 = 0.02525 -0.00381 0.00792 -0.00309 C13 1 0.708724 0.142730 0.248258 11.00000 0.02799 0.02914 = 0.01987 0.00254 0.00313 0.00325 C14 1 0.653207 0.244309 -0.230073 11.00000 0.05983 0.04202 = 0.02576 -0.00179 0.01335 -0.00482 C15 1 0.567147 0.300715 0.354827 11.00000 0.03530 0.05365 = 0.02361 -0.00024 0.00875 0.00389 N1 3 0.756615 0.226494 0.190443 11.00000 0.02940 0.03015 = 0.01845 -0.00052 0.00476 -0.00267 O1 4 0.638099 0.034832 0.218855 11.00000 0.03561 0.03435 = 0.02271 0.00224 0.00402 -0.00676 PART 1 F1A 5 0.605432 0.371875 -0.263604 21.00000 0.23434 0.11040 = 0.03826 0.03528 0.03593 0.12046 F2A 5 0.607342 0.114263 -0.274615 21.00000 0.13210 0.09687 = 0.02894 -0.02244 0.02503 -0.06255 F3A 5 0.750094 0.248313 -0.256040 21.00000 0.06813 0.16775 = 0.02508 -0.00073 0.02319 -0.02193 PART 2 F1B 5 0.673499 0.115705 -0.274405 -21.00000 0.17201 0.07092 = 0.03587 -0.00773 0.04281 0.04514 F2B 5 0.685978 0.376533 -0.264587 -21.00000 0.10213 0.07460 = 0.02684 0.00450 0.01358 -0.04554 F3B 5 0.537572 0.256987 -0.274885 -21.00000 0.05428 0.10931 = 0.02631 0.01607 -0.00305 -0.00616 PART 0 F4 5 0.557107 0.371838 0.265829 11.00000 0.04221 0.06371 = 0.02498 0.00988 0.00394 0.01637 F5 5 0.528621 0.410902 0.406269 11.00000 0.05104 0.08060 = 0.03582 -0.00448 0.01215 0.02494 F6 5 0.497069 0.172475 0.335673 11.00000 0.03282 0.07807 = 0.05073 -0.00081 0.00843 -0.00987 H1 2 0.803996 0.306421 0.219823 11.00000 0.03281 H3 2 0.674198 0.321182 0.542903 11.00000 0.04553 H4 2 0.854325 0.241964 0.631216 11.00000 0.04276 H5 2 0.972146 0.136132 0.551325 11.00000 0.04470 H6 2 0.909335 0.104686 0.375108 11.00000 0.03447 H8 2 0.594959 0.073406 0.052565 11.00000 0.03993 H9 2 0.548062 0.087584 -0.121921 11.00000 0.04437 H11 2 0.824033 0.374336 -0.086027 11.00000 0.03758 H12 2 0.861544 0.361274 0.086327 11.00000 0.03018 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.75155(10) 0.18601(16) 0.35774(9) 0.0272(3) Uani 1 1 d . . . C2 C 0.68328(10) 0.25049(16) 0.40870(9) 0.0293(3) Uani 1 1 d . . . C3 C 0.72291(12) 0.27092(19) 0.51154(10) 0.0359(3) Uani 1 1 d . . . C4 C 0.83050(12) 0.22610(19) 0.56389(11) 0.0388(4) Uani 1 1 d . . . C5 C 0.89858(12) 0.16591(19) 0.51362(10) 0.0379(4) Uani 1 1 d . . . C6 C 0.86007(11) 0.14691(17) 0.41078(10) 0.0326(3) Uani 1 1 d . . . C7 C 0.73111(10) 0.21794(15) 0.08562(9) 0.0244(3) Uani 1 1 d . . . C8 C 0.63973(11) 0.13413(18) 0.02431(10) 0.0315(3) Uani 1 1 d . . . C9 C 0.61585(12) 0.14270(18) -0.07816(10) 0.0324(3) Uani 1 1 d . . . C10 C 0.68251(11) 0.23230(16) -0.11969(9) 0.0299(3) Uani 1 1 d . A . C11 C 0.77557(12) 0.31195(18) -0.05851(10) 0.0339(3) Uani 1 1 d . . . C12 C 0.79979(11) 0.30393(18) 0.04399(10) 0.0306(3) Uani 1 1 d . . . C13 C 0.70872(10) 0.14273(16) 0.24826(9) 0.0267(3) Uani 1 1 d . . . C14 C 0.65321(14) 0.2443(2) -0.23007(10) 0.0426(4) Uani 1 1 d . . . C15 C 0.56715(12) 0.3007(2) 0.35483(10) 0.0376(3) Uani 1 1 d . . . N1 N 0.75662(9) 0.22649(14) 0.19044(8) 0.0266(2) Uani 1 1 d . . . O1 O 0.63810(7) 0.03483(11) 0.21885(6) 0.0321(2) Uani 1 1 d . . . F1A F 0.6054(7) 0.3719(7) -0.2636(3) 0.129(4) Uani 0.426(5) 1 d P A 1 F2A F 0.6073(5) 0.1143(7) -0.2746(3) 0.086(2) Uani 0.426(5) 1 d P A 1 F3A F 0.7501(3) 0.2483(8) -0.25604(19) 0.0850(19) Uani 0.426(5) 1 d P A 1 F1B F 0.6735(4) 0.1157(5) -0.2744(2) 0.0906(18) Uani 0.574(5) 1 d P A 2 F2B F 0.6860(3) 0.3765(4) -0.26459(15) 0.0694(14) Uani 0.574(5) 1 d P A 2 F3B F 0.53757(16) 0.2570(5) -0.27488(14) 0.0670(10) Uani 0.574(5) 1 d P A 2 F4 F 0.55711(6) 0.37184(11) 0.26583(6) 0.0452(2) Uani 1 1 d . . . F5 F 0.52862(7) 0.41090(13) 0.40627(6) 0.0562(3) Uani 1 1 d . . . F6 F 0.49707(7) 0.17247(13) 0.33567(7) 0.0550(3) Uani 1 1 d . . . H1 H 0.8040(12) 0.3064(17) 0.2198(11) 0.033(4) Uiso 1 1 d . . . H3 H 0.6742(12) 0.3212(18) 0.5429(12) 0.046(5) Uiso 1 1 d . . . H4 H 0.8543(12) 0.2420(18) 0.6312(12) 0.043(4) Uiso 1 1 d . . . H5 H 0.9721(13) 0.1361(18) 0.5513(12) 0.045(4) Uiso 1 1 d . . . H6 H 0.9093(12) 0.1047(17) 0.3751(10) 0.034(4) Uiso 1 1 d . . . H8 H 0.5950(12) 0.0734(17) 0.0526(11) 0.040(4) Uiso 1 1 d . . . H9 H 0.5481(12) 0.0876(18) -0.1219(12) 0.044(4) Uiso 1 1 d . . . H11 H 0.8240(12) 0.3743(17) -0.0860(11) 0.038(4) Uiso 1 1 d . . . H12 H 0.8615(11) 0.3613(17) 0.0863(10) 0.030(4) 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 C1 0.0318(6) 0.0288(7) 0.0182(6) 0.0032(5) 0.0037(5) -0.0018(5) C2 0.0312(6) 0.0334(7) 0.0203(6) 0.0029(5) 0.0039(5) -0.0026(6) C3 0.0429(8) 0.0419(8) 0.0213(6) 0.0006(6) 0.0075(6) -0.0025(7) C4 0.0461(8) 0.0459(9) 0.0172(6) 0.0029(6) -0.0006(6) -0.0039(7) C5 0.0329(7) 0.0455(9) 0.0265(7) 0.0063(6) -0.0034(6) 0.0006(7) C6 0.0312(7) 0.0368(8) 0.0259(7) 0.0038(6) 0.0036(6) 0.0018(6) C7 0.0269(6) 0.0261(6) 0.0191(6) -0.0004(5) 0.0057(5) 0.0036(5) C8 0.0323(7) 0.0383(8) 0.0225(6) 0.0014(6) 0.0067(5) -0.0063(6) C9 0.0346(7) 0.0385(8) 0.0207(6) -0.0014(5) 0.0038(5) -0.0028(6) C10 0.0381(7) 0.0309(7) 0.0215(6) -0.0022(5) 0.0105(5) 0.0026(6) C11 0.0384(7) 0.0400(8) 0.0270(7) -0.0013(6) 0.0158(6) -0.0052(7) C12 0.0293(6) 0.0367(7) 0.0252(7) -0.0038(6) 0.0079(5) -0.0031(6) C13 0.0280(6) 0.0291(7) 0.0199(6) 0.0025(5) 0.0031(5) 0.0033(5) C14 0.0598(10) 0.0420(9) 0.0258(7) -0.0018(6) 0.0133(7) -0.0048(8) C15 0.0353(7) 0.0537(9) 0.0236(7) -0.0002(6) 0.0087(6) 0.0039(7) N1 0.0294(5) 0.0302(6) 0.0184(5) -0.0005(4) 0.0048(4) -0.0027(5) O1 0.0356(5) 0.0343(5) 0.0227(5) 0.0022(4) 0.0040(4) -0.0068(4) F1A 0.234(9) 0.110(5) 0.0383(18) 0.035(2) 0.036(4) 0.120(6) F2A 0.132(4) 0.097(4) 0.0289(15) -0.0224(17) 0.025(2) -0.063(4) F3A 0.068(2) 0.168(5) 0.0251(13) -0.0007(19) 0.0232(12) -0.022(3) F1B 0.172(4) 0.071(3) 0.0359(12) -0.0077(12) 0.043(2) 0.045(3) F2B 0.102(2) 0.075(3) 0.0268(10) 0.0045(11) 0.0136(13) -0.046(2) F3B 0.0543(12) 0.109(2) 0.0263(9) 0.0161(11) -0.0031(8) -0.0062(14) F4 0.0422(5) 0.0637(6) 0.0250(4) 0.0099(4) 0.0039(4) 0.0164(4) F5 0.0510(5) 0.0806(7) 0.0358(5) -0.0045(5) 0.0121(4) 0.0249(5) F6 0.0328(4) 0.0781(7) 0.0507(6) -0.0008(5) 0.0084(4) -0.0099(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C6 1.3946(18) . ? C1 C2 1.3987(19) . ? C1 C13 1.5130(17) . ? C2 C3 1.3923(18) . ? C2 C15 1.5005(19) . ? C3 C4 1.394(2) . ? C3 H3 0.963(16) . ? C4 C5 1.377(2) . ? C4 H4 0.913(15) . ? C5 C6 1.3906(19) . ? C5 H5 0.957(16) . ? C6 H6 0.986(15) . ? C7 C12 1.3899(18) . ? C7 C8 1.3943(18) . ? C7 N1 1.4169(16) . ? C8 C9 1.3867(19) . ? C8 H8 0.935(15) . ? C9 C10 1.3841(19) . ? C9 H9 0.999(15) . ? C10 C11 1.3920(19) . ? C10 C14 1.4907(19) . ? C11 C12 1.3864(19) . ? C11 H11 0.972(15) . ? C12 H12 0.950(13) . ? C13 O1 1.2304(15) . ? C13 N1 1.3492(17) . ? C14 F1A 1.215(3) . ? C14 F2A 1.269(5) . ? C14 F1B 1.280(3) . ? C14 F2B 1.297(3) . ? C14 F3A 1.404(3) . ? C14 F3B 1.422(3) . ? C15 F5 1.3381(17) . ? C15 F6 1.3408(19) . ? C15 F4 1.3528(16) . ? N1 H1 0.894(15) . ? 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 C6 C1 C2 119.21(12) . . ? C6 C1 C13 118.59(12) . . ? C2 C1 C13 121.97(11) . . ? C3 C2 C1 120.08(12) . . ? C3 C2 C15 118.49(12) . . ? C1 C2 C15 121.43(11) . . ? C2 C3 C4 120.00(14) . . ? C2 C3 H3 117.1(9) . . ? C4 C3 H3 122.9(9) . . ? C5 C4 C3 120.01(13) . . ? C5 C4 H4 122.0(9) . . ? C3 C4 H4 117.9(9) . . ? C4 C5 C6 120.37(13) . . ? C4 C5 H5 118.4(10) . . ? C6 C5 H5 121.3(10) . . ? C5 C6 C1 120.28(14) . . ? C5 C6 H6 120.0(8) . . ? C1 C6 H6 119.7(8) . . ? C12 C7 C8 119.95(12) . . ? C12 C7 N1 116.83(11) . . ? C8 C7 N1 123.17(12) . . ? C9 C8 C7 119.50(13) . . ? C9 C8 H8 120.7(9) . . ? C7 C8 H8 119.8(9) . . ? C10 C9 C8 120.51(13) . . ? C10 C9 H9 120.2(9) . . ? C8 C9 H9 119.3(9) . . ? C9 C10 C11 120.04(12) . . ? C9 C10 C14 119.56(12) . . ? C11 C10 C14 120.40(13) . . ? C12 C11 C10 119.69(13) . . ? C12 C11 H11 118.9(8) . . ? C10 C11 H11 121.4(8) . . ? C11 C12 C7 120.25(12) . . ? C11 C12 H12 120.3(9) . . ? C7 C12 H12 119.3(9) . . ? O1 C13 N1 125.20(12) . . ? O1 C13 C1 120.06(11) . . ? N1 C13 C1 114.70(11) . . ? F1A C14 F2A 114.0(4) . . ? F1A C14 F1B 130.5(3) . . ? F2A C14 F2B 130.3(2) . . ? F1B C14 F2B 109.9(2) . . ? F1A C14 F3A 105.0(4) . . ? F2A C14 F3A 101.5(3) . . ? F1B C14 F3B 100.6(2) . . ? F2B C14 F3B 100.9(2) . . ? F3A C14 F3B 140.15(18) . . ? F1A C14 C10 113.2(2) . . ? F2A C14 C10 113.1(2) . . ? F1B C14 C10 115.98(19) . . ? F2B C14 C10 116.34(15) . . ? F3A C14 C10 108.91(16) . . ? F3B C14 C10 110.83(14) . . ? F5 C15 F6 106.41(12) . . ? F5 C15 F4 106.40(12) . . ? F6 C15 F4 106.10(11) . . ? F5 C15 C2 112.38(12) . . ? F6 C15 C2 112.99(13) . . ? F4 C15 C2 112.07(11) . . ? C13 N1 C7 127.71(11) . . ? C13 N1 H1 116.9(9) . . ? C7 N1 H1 114.9(10) . . ? 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 C6 C1 C2 C3 -1.69(19) . . . . ? C13 C1 C2 C3 172.68(12) . . . . ? C6 C1 C2 C15 177.65(13) . . . . ? C13 C1 C2 C15 -7.97(19) . . . . ? C1 C2 C3 C4 -0.4(2) . . . . ? C15 C2 C3 C4 -179.78(13) . . . . ? C2 C3 C4 C5 1.8(2) . . . . ? C3 C4 C5 C6 -1.1(2) . . . . ? C4 C5 C6 C1 -1.1(2) . . . . ? C2 C1 C6 C5 2.4(2) . . . . ? C13 C1 C6 C5 -172.12(12) . . . . ? C12 C7 C8 C9 -2.5(2) . . . . ? N1 C7 C8 C9 174.93(12) . . . . ? C7 C8 C9 C10 0.6(2) . . . . ? C8 C9 C10 C11 1.3(2) . . . . ? C8 C9 C10 C14 -178.02(13) . . . . ? C9 C10 C11 C12 -1.3(2) . . . . ? C14 C10 C11 C12 177.97(13) . . . . ? C10 C11 C12 C7 -0.5(2) . . . . ? C8 C7 C12 C11 2.4(2) . . . . ? N1 C7 C12 C11 -175.12(12) . . . . ? C6 C1 C13 O1 112.21(15) . . . . ? C2 C1 C13 O1 -62.20(17) . . . . ? C6 C1 C13 N1 -65.65(16) . . . . ? C2 C1 C13 N1 119.94(14) . . . . ? C9 C10 C14 F1A 97.9(5) . . . . ? C11 C10 C14 F1A -81.4(5) . . . . ? C9 C10 C14 F2A -33.7(4) . . . . ? C11 C10 C14 F2A 147.0(4) . . . . ? C9 C10 C14 F1B -76.5(3) . . . . ? C11 C10 C14 F1B 104.2(3) . . . . ? C9 C10 C14 F2B 151.9(3) . . . . ? C11 C10 C14 F2B -27.5(3) . . . . ? C9 C10 C14 F3A -145.8(3) . . . . ? C11 C10 C14 F3A 34.9(3) . . . . ? C9 C10 C14 F3B 37.3(3) . . . . ? C11 C10 C14 F3B -142.0(2) . . . . ? C3 C2 C15 F5 22.10(19) . . . . ? C1 C2 C15 F5 -157.26(12) . . . . ? C3 C2 C15 F6 -98.34(15) . . . . ? C1 C2 C15 F6 82.30(15) . . . . ? C3 C2 C15 F4 141.85(13) . . . . ? C1 C2 C15 F4 -37.50(19) . . . . ? O1 C13 N1 C7 5.1(2) . . . . ? C1 C13 N1 C7 -177.20(11) . . . . ? C12 C7 N1 C13 -173.60(12) . . . . ? C8 C7 N1 C13 8.9(2) . . . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.277 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.046 # Attachment 't-3-2.cif' data_T-3-2 _database_code_depnum_ccdc_archive 'CCDC 826200' #TrackingRef 't-3-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H9 F6 N O' _chemical_formula_sum 'C15 H9 F6 N O' _chemical_formula_weight 333.23 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ab 2ac' _symmetry_space_group_name_H-M 'P c c n' _symmetry_Int_Tables_number 56 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' 'x+1/2, -y, -z+1/2' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' '-x-1/2, y, z-1/2' 'x, -y-1/2, z-1/2' _cell_length_a 25.559(5) _cell_length_b 11.622(5) _cell_length_c 9.509(5) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2825(2) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 966 _cell_measurement_theta_min 1.75 _cell_measurement_theta_max 25.75 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.567 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9253 _exptl_absorpt_correction_T_max 0.9784 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 30904 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0299 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 29.32 _reflns_number_total 3591 _reflns_number_gt 2564 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+1.1986P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3591 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0783 _refine_ls_R_factor_gt 0.0538 _refine_ls_wR_factor_ref 0.1572 _refine_ls_wR_factor_gt 0.1461 _refine_ls_goodness_of_fit_ref 1.100 _refine_ls_restrained_S_all 1.100 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-3-2 in P c c n CELL 0.71073 25.559 11.622 9.509 90.000 90.000 90.000 ZERR 8 0.005 0.005 0.005 0.005 0.005 0.005 LATT 1 SYMM 0.50000-X, 0.50000-Y,Z SYMM 0.50000+X,-Y, 0.50000-Z SYMM -X, 0.50000+Y, 0.50000-Z SFAC C H N O F UNIT 120 72 8 8 48 MERG 2 L.S. 12 ACTA 50 HTAB BOND $H CONF temp -153 FMAP 2 PLAN 15 WGHT 0.080000 1.198600 FVAR 4.15049 0.88857 C1 1 0.815755 -0.003272 0.072947 11.00000 0.02007 0.01909 = 0.01442 -0.00323 -0.00095 0.00110 C2 1 0.866402 0.029211 0.035948 11.00000 0.02353 0.02443 = 0.01842 0.00124 0.00215 -0.00109 C3 1 0.909136 -0.016784 0.106809 11.00000 0.01840 0.02874 = 0.02684 -0.00186 0.00067 -0.00153 C4 1 0.901650 -0.096353 0.213145 11.00000 0.02294 0.02465 = 0.02623 -0.00331 -0.00615 0.00440 C5 1 0.851240 -0.130089 0.248343 11.00000 0.02491 0.01933 = 0.01931 -0.00017 -0.00331 0.00174 C6 1 0.808030 -0.083682 0.178923 11.00000 0.01857 0.02068 = 0.01760 0.00021 -0.00088 0.00041 C7 1 0.676552 0.095864 0.019820 11.00000 0.02037 0.02099 = 0.01832 -0.00352 -0.00250 0.00411 C8 1 0.668941 0.159630 -0.102743 11.00000 0.02521 0.01992 = 0.02033 -0.00066 -0.00094 0.00241 C9 1 0.618386 0.190121 -0.140977 11.00000 0.02944 0.02083 = 0.02374 -0.00226 -0.00471 0.00493 C10 1 0.575916 0.159361 -0.058431 11.00000 0.02271 0.02674 = 0.02761 -0.00728 -0.00524 0.00483 C11 1 0.583390 0.095604 0.062685 11.00000 0.02333 0.03480 = 0.02704 -0.00345 0.00397 0.00060 C12 1 0.633554 0.063274 0.101415 11.00000 0.02702 0.03088 = 0.01926 0.00148 0.00018 0.00279 C13 1 0.770783 0.047434 -0.007189 11.00000 0.02175 0.01817 = 0.01533 -0.00069 -0.00134 -0.00068 C14 1 0.522390 0.197390 -0.101406 11.00000 0.02385 0.04344 = 0.03761 -0.00414 -0.00424 0.00811 C15 1 0.841693 -0.220067 0.357794 11.00000 0.03510 0.02624 = 0.02940 0.00622 -0.00903 -0.00021 N1 3 0.726475 0.062254 0.068903 11.00000 0.02242 0.02870 = 0.01268 0.00200 -0.00215 0.00599 O1 4 0.775040 0.072630 -0.132074 11.00000 0.02543 0.03148 = 0.01328 0.00224 -0.00033 0.00220 F1 5 0.509061 0.164234 -0.227156 11.00000 0.04870 0.18870 = 0.06407 -0.06059 -0.03548 0.05456 F2 5 0.518500 0.311946 -0.104664 11.00000 0.04295 0.05257 = 0.16211 0.00482 -0.03168 0.02141 F3 5 0.485174 0.163350 -0.015878 11.00000 0.02424 0.12462 = 0.08149 0.03156 0.00368 0.01345 PART 1 F4A 5 0.818254 -0.313587 0.306088 21.00000 0.07034 0.02787 = 0.04378 0.00956 -0.01043 -0.01979 F5A 5 0.806168 -0.185100 0.455281 21.00000 0.07752 0.04365 = 0.03795 0.01471 0.02434 0.00854 F6A 5 0.883034 -0.248361 0.430099 21.00000 0.04094 0.09617 = 0.08542 0.07078 -0.03157 -0.01578 PART 2 F4B 5 0.845242 -0.188670 0.474751 -21.00000 0.04339 F5B 5 0.886894 -0.301644 0.335838 -21.00000 0.04552 F6B 5 0.847101 -0.317979 0.313900 -21.00000 0.06303 PART 0 H1 2 0.728389 0.050103 0.163118 11.00000 0.02285 H2 2 0.872027 0.082628 -0.037461 11.00000 0.01705 H3 2 0.942590 0.010331 0.085971 11.00000 0.03178 H4 2 0.932089 -0.129551 0.262815 11.00000 0.02607 H6 2 0.774052 -0.107890 0.204588 11.00000 0.03209 H8 2 0.698284 0.188015 -0.155655 11.00000 0.02324 H9 2 0.614135 0.232794 -0.226100 11.00000 0.03975 H11 2 0.556844 0.072302 0.121422 11.00000 0.03650 H12 2 0.638969 0.020900 0.182750 11.00000 0.03054 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.81576(7) -0.00327(16) 0.07295(18) 0.0179(4) Uani 1 1 d . . . C2 C 0.86640(7) 0.02921(17) 0.03595(19) 0.0221(4) Uani 1 1 d . . . C3 C 0.90914(7) -0.01678(18) 0.1068(2) 0.0247(4) Uani 1 1 d . . . C4 C 0.90165(7) -0.09635(17) 0.2131(2) 0.0246(4) Uani 1 1 d . . . C5 C 0.85124(7) -0.13009(16) 0.24834(19) 0.0212(4) Uani 1 1 d . A . C6 C 0.80803(7) -0.08368(16) 0.17892(18) 0.0190(4) Uani 1 1 d . . . C7 C 0.67655(7) 0.09586(16) 0.01982(19) 0.0199(4) Uani 1 1 d . . . C8 C 0.66894(7) 0.15963(16) -0.10274(19) 0.0218(4) Uani 1 1 d . . . C9 C 0.61839(8) 0.19012(17) -0.1410(2) 0.0247(4) Uani 1 1 d . . . C10 C 0.57592(7) 0.15936(17) -0.0584(2) 0.0257(4) Uani 1 1 d . . . C11 C 0.58339(8) 0.09560(19) 0.0627(2) 0.0284(4) Uani 1 1 d . . . C12 C 0.63355(8) 0.06327(18) 0.1014(2) 0.0257(4) Uani 1 1 d . . . C13 C 0.77078(7) 0.04743(15) -0.00719(18) 0.0184(4) Uani 1 1 d . . . C14 C 0.52239(8) 0.1974(2) -0.1014(2) 0.0350(5) Uani 1 1 d . . . C15 C 0.84169(8) -0.22007(18) 0.3578(2) 0.0302(5) Uani 1 1 d . . . N1 N 0.72648(6) 0.06225(14) 0.06890(16) 0.0213(3) Uani 1 1 d . . . O1 O 0.77504(5) 0.07263(12) -0.13207(13) 0.0234(3) Uani 1 1 d . . . F1 F 0.50906(7) 0.1642(2) -0.2272(2) 0.1005(9) Uani 1 1 d . . . F2 F 0.51850(7) 0.31195(16) -0.1047(3) 0.0859(7) Uani 1 1 d . . . F3 F 0.48517(5) 0.16335(19) -0.0159(2) 0.0768(6) Uani 1 1 d . . . F4A F 0.81825(11) -0.31359(14) 0.30609(18) 0.0473(6) Uani 0.889(4) 1 d P A 1 F5A F 0.80617(9) -0.18510(14) 0.45528(17) 0.0530(7) Uani 0.889(4) 1 d P A 1 F6A F 0.88303(7) -0.2484(2) 0.4301(3) 0.0742(10) Uani 0.889(4) 1 d P A 1 F4B F 0.8452(6) -0.1887(11) 0.4748(14) 0.043(4) Uiso 0.111(4) 1 d P A 2 F5B F 0.8869(6) -0.3016(12) 0.3358(17) 0.046(4) Uiso 0.111(4) 1 d P A 2 F6B F 0.8471(10) -0.3180(17) 0.314(2) 0.063(5) Uiso 0.111(4) 1 d P A 2 H1 H 0.7284(8) 0.0501(18) 0.163(2) 0.023(5) Uiso 1 1 d . . . H2 H 0.8720(7) 0.0826(18) -0.037(2) 0.017(5) Uiso 1 1 d . . . H3 H 0.9426(9) 0.010(2) 0.086(2) 0.032(6) Uiso 1 1 d . . . H4 H 0.9321(8) -0.1296(19) 0.263(2) 0.026(5) Uiso 1 1 d . . . H6 H 0.7741(9) -0.108(2) 0.205(2) 0.032(6) Uiso 1 1 d . . . H8 H 0.6983(8) 0.1880(19) -0.156(2) 0.023(5) Uiso 1 1 d . . . H9 H 0.6141(9) 0.233(2) -0.226(3) 0.040(7) Uiso 1 1 d . . . H11 H 0.5568(10) 0.072(2) 0.121(2) 0.036(6) Uiso 1 1 d . . . H12 H 0.6390(8) 0.021(2) 0.183(2) 0.031(6) 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 C1 0.0201(8) 0.0191(9) 0.0144(8) -0.0032(6) -0.0010(6) 0.0011(7) C2 0.0235(9) 0.0244(10) 0.0184(9) 0.0012(7) 0.0021(7) -0.0011(7) C3 0.0184(9) 0.0287(10) 0.0268(10) -0.0019(8) 0.0007(7) -0.0015(7) C4 0.0229(9) 0.0247(10) 0.0262(10) -0.0033(8) -0.0061(7) 0.0044(7) C5 0.0249(9) 0.0193(9) 0.0193(9) -0.0002(7) -0.0033(7) 0.0017(7) C6 0.0186(8) 0.0207(9) 0.0176(8) 0.0002(7) -0.0009(6) 0.0004(7) C7 0.0204(8) 0.0210(9) 0.0183(9) -0.0035(7) -0.0025(6) 0.0041(7) C8 0.0252(9) 0.0199(9) 0.0203(9) -0.0007(7) -0.0009(7) 0.0024(7) C9 0.0294(10) 0.0208(10) 0.0237(10) -0.0023(8) -0.0047(8) 0.0049(7) C10 0.0227(9) 0.0267(10) 0.0276(10) -0.0073(8) -0.0052(7) 0.0048(8) C11 0.0233(9) 0.0348(11) 0.0270(10) -0.0034(8) 0.0040(8) 0.0006(8) C12 0.0270(10) 0.0309(11) 0.0193(9) 0.0015(8) 0.0002(7) 0.0028(8) C13 0.0218(8) 0.0182(8) 0.0153(8) -0.0007(7) -0.0013(6) -0.0007(7) C14 0.0239(10) 0.0434(13) 0.0376(12) -0.0041(10) -0.0042(8) 0.0081(9) C15 0.0351(11) 0.0262(11) 0.0294(11) 0.0062(8) -0.0090(8) -0.0002(8) N1 0.0224(8) 0.0287(9) 0.0127(7) 0.0020(6) -0.0022(6) 0.0060(6) O1 0.0254(7) 0.0315(8) 0.0133(6) 0.0022(5) -0.0003(5) 0.0022(6) F1 0.0487(10) 0.189(3) 0.0641(12) -0.0606(13) -0.0355(9) 0.0546(12) F2 0.0429(9) 0.0526(11) 0.162(2) 0.0048(12) -0.0317(11) 0.0214(8) F3 0.0242(7) 0.1246(17) 0.0815(13) 0.0316(12) 0.0037(8) 0.0135(8) F4A 0.0703(15) 0.0279(9) 0.0438(10) 0.0096(7) -0.0104(9) -0.0198(8) F5A 0.0775(16) 0.0437(10) 0.0379(10) 0.0147(7) 0.0243(9) 0.0085(9) F6A 0.0409(10) 0.0962(18) 0.0854(18) 0.0708(16) -0.0316(10) -0.0158(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C6 1.388(3) . ? C1 C2 1.394(2) . ? C1 C13 1.500(2) . ? C2 C3 1.390(3) . ? C2 H2 0.95(2) . ? C3 C4 1.384(3) . ? C3 H3 0.93(2) . ? C4 C5 1.388(3) . ? C4 H4 0.99(2) . ? C5 C6 1.395(2) . ? C5 C15 1.495(3) . ? C6 H6 0.94(2) . ? C7 C8 1.395(3) . ? C7 C12 1.398(3) . ? C7 N1 1.414(2) . ? C8 C9 1.388(3) . ? C8 H8 0.96(2) . ? C9 C10 1.386(3) . ? C9 H9 0.96(3) . ? C10 C11 1.383(3) . ? C10 C14 1.495(3) . ? C11 C12 1.386(3) . ? C11 H11 0.92(2) . ? C12 H12 0.93(2) . ? C13 O1 1.228(2) . ? C13 N1 1.355(2) . ? C14 F1 1.302(3) . ? C14 F3 1.313(3) . ? C14 F2 1.335(3) . ? C15 F4B 1.174(13) . ? C15 F6B 1.220(19) . ? C15 F6A 1.303(2) . ? C15 F4A 1.335(3) . ? C15 F5A 1.360(3) . ? C15 F5B 1.509(14) . ? N1 H1 0.91(2) . ? F5B F6B 1.06(3) . ? 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 C6 C1 C2 119.85(16) . . ? C6 C1 C13 121.62(16) . . ? C2 C1 C13 118.50(16) . . ? C3 C2 C1 120.22(18) . . ? C3 C2 H2 119.4(12) . . ? C1 C2 H2 120.4(12) . . ? C4 C3 C2 120.17(17) . . ? C4 C3 H3 120.5(14) . . ? C2 C3 H3 119.2(14) . . ? C3 C4 C5 119.57(17) . . ? C3 C4 H4 120.1(13) . . ? C5 C4 H4 120.3(13) . . ? C4 C5 C6 120.77(17) . . ? C4 C5 C15 121.13(17) . . ? C6 C5 C15 118.07(17) . . ? C1 C6 C5 119.41(17) . . ? C1 C6 H6 121.2(14) . . ? C5 C6 H6 119.4(14) . . ? C8 C7 C12 119.88(17) . . ? C8 C7 N1 123.27(17) . . ? C12 C7 N1 116.84(17) . . ? C9 C8 C7 118.96(18) . . ? C9 C8 H8 120.1(13) . . ? C7 C8 H8 120.7(13) . . ? C10 C9 C8 120.97(18) . . ? C10 C9 H9 121.6(14) . . ? C8 C9 H9 117.4(14) . . ? C11 C10 C9 120.10(18) . . ? C11 C10 C14 120.84(19) . . ? C9 C10 C14 119.05(19) . . ? C10 C11 C12 119.63(19) . . ? C10 C11 H11 124.2(15) . . ? C12 C11 H11 116.2(15) . . ? C11 C12 C7 120.43(18) . . ? C11 C12 H12 120.2(14) . . ? C7 C12 H12 119.3(14) . . ? O1 C13 N1 124.07(16) . . ? O1 C13 C1 121.14(15) . . ? N1 C13 C1 114.79(15) . . ? F1 C14 F3 106.9(2) . . ? F1 C14 F2 104.7(2) . . ? F3 C14 F2 105.1(2) . . ? F1 C14 C10 113.78(18) . . ? F3 C14 C10 113.9(2) . . ? F2 C14 C10 111.67(19) . . ? F4B C15 F6B 127.2(12) . . ? F6B C15 F6A 81.6(12) . . ? F4B C15 F4A 129.5(7) . . ? F6A C15 F4A 110.7(2) . . ? F4B C15 F5A 46.6(7) . . ? F6B C15 F5A 126.0(10) . . ? F6A C15 F5A 104.9(2) . . ? F4A C15 F5A 101.2(2) . . ? F4B C15 C5 115.4(7) . . ? F6B C15 C5 113.3(9) . . ? F6A C15 C5 114.30(18) . . ? F4A C15 C5 112.72(17) . . ? F5A C15 C5 111.99(17) . . ? F4B C15 F5B 105.5(9) . . ? F5A C15 F5B 142.5(6) . . ? C5 C15 F5B 102.6(6) . . ? C13 N1 C7 127.82(15) . . ? C13 N1 H1 117.5(13) . . ? C7 N1 H1 114.7(13) . . ? F5B F6B C15 82.7(18) . . ? 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 C6 C1 C2 C3 -1.4(3) . . . . ? C13 C1 C2 C3 -179.36(17) . . . . ? C1 C2 C3 C4 0.9(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C3 C4 C5 C15 176.99(18) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? C13 C1 C6 C5 178.65(16) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C15 C5 C6 C1 -177.50(17) . . . . ? C12 C7 C8 C9 0.3(3) . . . . ? N1 C7 C8 C9 -178.93(17) . . . . ? C7 C8 C9 C10 0.8(3) . . . . ? C8 C9 C10 C11 -1.2(3) . . . . ? C8 C9 C10 C14 178.03(19) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? C14 C10 C11 C12 -178.82(19) . . . . ? C10 C11 C12 C7 0.8(3) . . . . ? C8 C7 C12 C11 -1.1(3) . . . . ? N1 C7 C12 C11 178.19(17) . . . . ? C6 C1 C13 O1 -145.95(18) . . . . ? C2 C1 C13 O1 32.0(3) . . . . ? C6 C1 C13 N1 34.0(2) . . . . ? C2 C1 C13 N1 -148.02(17) . . . . ? C11 C10 C14 F1 -123.7(3) . . . . ? C9 C10 C14 F1 57.1(3) . . . . ? C11 C10 C14 F3 -0.9(3) . . . . ? C9 C10 C14 F3 179.9(2) . . . . ? C11 C10 C14 F2 118.0(2) . . . . ? C9 C10 C14 F2 -61.2(3) . . . . ? C4 C5 C15 F4B 78.6(9) . . . . ? C6 C5 C15 F4B -103.6(9) . . . . ? C4 C5 C15 F6B -80.6(14) . . . . ? C6 C5 C15 F6B 97.2(14) . . . . ? C4 C5 C15 F6A 10.5(3) . . . . ? C6 C5 C15 F6A -171.7(2) . . . . ? C4 C5 C15 F4A -117.0(2) . . . . ? C6 C5 C15 F4A 60.8(3) . . . . ? C4 C5 C15 F5A 129.6(2) . . . . ? C6 C5 C15 F5A -52.5(2) . . . . ? C4 C5 C15 F5B -35.6(7) . . . . ? C6 C5 C15 F5B 142.2(6) . . . . ? O1 C13 N1 C7 7.5(3) . . . . ? C1 C13 N1 C7 -172.51(17) . . . . ? C8 C7 N1 C13 -25.0(3) . . . . ? C12 C7 N1 C13 155.71(18) . . . . ? F4B C15 F5B F6B 128.1(16) . . . . ? F6A C15 F5B F6B 137.5(17) . . . . ? F4A C15 F5B F6B 0.2(14) . . . . ? F5A C15 F5B F6B 92.2(17) . . . . ? C5 C15 F5B F6B -110.6(14) . . . . ? F4B C15 F6B F5B -72.2(19) . . . . ? F6A C15 F6B F5B -28.9(12) . . . . ? F4A C15 F6B F5B -180(3) . . . . ? F5A C15 F6B F5B -131.2(12) . . . . ? C5 C15 F6B F5B 84.0(15) . . . . ? _diffrn_measured_fraction_theta_max 0.926 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.657 _refine_diff_density_min -0.519 _refine_diff_density_rms 0.059 # Attachment 't-3-3.cif' data_T-3-3 _database_code_depnum_ccdc_archive 'CCDC 826201' #TrackingRef 't-3-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H9 F6 N O' _chemical_formula_sum 'C15 H9 F6 N O' _chemical_formula_weight 333.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_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' _cell_length_a 5.2019(3) _cell_length_b 14.3865(7) _cell_length_c 18.1844(9) _cell_angle_alpha 90 _cell_angle_beta 97.367(5) _cell_angle_gamma 90 _cell_volume 1349.63(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 597 _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 25.45 _exptl_crystal_description plates _exptl_crystal_colour colorless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.160 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9235 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12483 _diffrn_reflns_av_R_equivalents 0.0609 _diffrn_reflns_av_sigmaI/netI 0.0502 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2372 _reflns_number_gt 1707 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0577P)^2^+0.8840P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2372 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0568 _refine_ls_wR_factor_ref 0.1504 _refine_ls_wR_factor_gt 0.1331 _refine_ls_goodness_of_fit_ref 1.083 _refine_ls_restrained_S_all 1.083 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-3-3 in P 1 21/n 1 CELL 0.71073 5.2019 14.3865 18.1844 90.000 97.367 90.000 ZERR 4 0.0003 0.0007 0.0009 0.000 0.005 0.000 LATT 1 SYMM 0.50000-X, 0.50000+Y, 0.50000-Z SFAC C H N O F UNIT 60 36 4 4 24 MERG 2 L.S. 12 TEMP -153 ACTA 50 OMIT 0 50 HTAB BOND $H CONF FMAP 2 PLAN 15 WGHT 0.057700 0.884000 FVAR 5.08774 0.47259 C1 1 0.232344 0.000819 0.131885 11.00000 0.03550 0.02158 = 0.02450 0.00131 -0.00054 0.00149 C2 1 0.096164 0.020758 0.190756 11.00000 0.02935 0.02290 = 0.03032 0.00333 0.00124 -0.00166 C3 1 0.166566 0.094639 0.237082 11.00000 0.02983 0.02478 = 0.02447 0.00176 0.00504 0.00411 C4 1 0.373070 0.150712 0.224250 11.00000 0.03020 0.02135 = 0.02444 -0.00098 0.00257 0.00248 C5 1 0.510008 0.132199 0.165763 11.00000 0.02629 0.03149 = 0.03085 0.00413 0.00555 -0.00186 C6 1 0.441427 0.056285 0.120077 11.00000 0.03560 0.03033 = 0.02230 -0.00096 0.00565 0.00949 C7 1 0.279791 -0.209489 0.010227 11.00000 0.03582 0.02589 = 0.01849 -0.00175 0.00364 -0.00642 C8 1 0.058854 -0.222091 -0.040978 11.00000 0.03312 0.02774 = 0.03216 0.00152 0.00799 0.00823 C9 1 0.034788 -0.301633 -0.083914 11.00000 0.02583 0.03288 = 0.02536 -0.00183 -0.00065 -0.00293 C10 1 0.229626 -0.368176 -0.076215 11.00000 0.02935 0.02590 = 0.02273 -0.00352 0.00509 -0.00150 C11 1 0.447540 -0.354646 -0.025068 11.00000 0.02898 0.03051 = 0.03365 -0.00159 0.00074 0.00256 C12 1 0.472797 -0.275326 0.017527 11.00000 0.03222 0.03107 = 0.02900 0.00119 -0.00272 0.00002 C13 1 0.135354 -0.079181 0.082266 11.00000 0.03060 0.03045 = 0.03029 0.00995 0.00577 0.00435 C14 1 0.197449 -0.455108 -0.120673 11.00000 0.04178 0.03508 = 0.03839 -0.00887 0.00671 -0.00028 C15 1 0.449077 0.230697 0.274771 11.00000 0.04084 0.03181 = 0.03432 -0.00455 0.00372 -0.00254 N1 3 0.322994 -0.127424 0.054657 11.00000 0.02558 0.03412 = 0.03175 0.00117 0.00257 -0.00037 O1 4 -0.098279 -0.097670 0.068901 11.00000 0.01529 0.03346 = 0.03902 -0.00717 0.00433 -0.00143 F1 5 0.098872 -0.439752 -0.191057 11.00000 0.09520 0.04948 = 0.04045 -0.01764 -0.01252 -0.00098 F2 5 0.417000 -0.500294 -0.123811 11.00000 0.06026 0.06313 = 0.08092 -0.03673 0.00501 0.02091 F3 5 0.041364 -0.515819 -0.093466 11.00000 0.09493 0.04016 = 0.08001 -0.02333 0.03444 -0.03011 PART 1 F4A 5 0.425385 0.212226 0.346647 21.00000 0.11301 0.04374 = 0.02585 -0.01339 0.00752 -0.01493 F5A 5 0.320366 0.304356 0.260095 21.00000 0.13027 0.03759 = 0.07565 -0.02393 -0.06174 0.04338 F6A 5 0.698051 0.254602 0.280640 21.00000 0.04882 0.10143 = 0.14289 -0.09171 0.04440 -0.04916 PART 2 F4B 5 0.514787 0.304137 0.236862 -21.00000 0.13391 0.03093 = 0.06112 -0.00975 0.01771 -0.03674 F5B 5 0.641285 0.211001 0.321026 -21.00000 0.11155 0.05827 = 0.10127 -0.03100 -0.08486 0.02140 F6B 5 0.259635 0.262515 0.307002 -21.00000 0.07407 0.08913 = 0.12975 -0.08120 0.06031 -0.02992 PART 0 H1 2 0.465998 -0.098097 0.076847 11.00000 0.07505 H2 2 -0.039753 -0.021102 0.198131 11.00000 0.03812 H3 2 0.074384 0.107134 0.279825 11.00000 0.03287 H5 2 0.642801 0.169248 0.156347 11.00000 0.02117 H6 2 0.536167 0.043457 0.079394 11.00000 0.03097 H8 2 -0.064631 -0.179274 -0.047003 11.00000 0.03316 H9 2 -0.112465 -0.311172 -0.120346 11.00000 0.02770 H11 2 0.591228 -0.401238 -0.019848 11.00000 0.03352 H12 2 0.628792 -0.265808 0.055877 11.00000 0.03495 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2323(5) 0.00082(18) 0.13188(15) 0.0276(7) Uani 1 1 d . . . C2 C 0.0962(6) 0.02076(19) 0.19076(15) 0.0278(7) Uani 1 1 d . . . C3 C 0.1666(5) 0.09464(19) 0.23708(15) 0.0262(6) Uani 1 1 d . . . C4 C 0.3731(5) 0.15071(19) 0.22425(14) 0.0254(6) Uani 1 1 d . A . C5 C 0.5100(6) 0.1322(2) 0.16576(15) 0.0294(7) Uani 1 1 d . . . C6 C 0.4414(6) 0.0563(2) 0.12008(15) 0.0292(7) Uani 1 1 d . . . C7 C 0.2798(5) -0.20949(19) 0.01023(14) 0.0267(7) Uani 1 1 d . . . C8 C 0.0589(6) -0.2221(2) -0.04098(16) 0.0307(7) Uani 1 1 d . . . C9 C 0.0348(6) -0.3016(2) -0.08391(15) 0.0284(7) Uani 1 1 d . . . C10 C 0.2296(5) -0.36818(19) -0.07621(14) 0.0258(6) Uani 1 1 d . . . C11 C 0.4475(6) -0.3546(2) -0.02507(16) 0.0313(7) Uani 1 1 d . . . C12 C 0.4728(6) -0.2753(2) 0.01753(15) 0.0313(7) Uani 1 1 d . . . C13 C 0.1354(6) -0.0792(2) 0.08227(15) 0.0303(7) Uani 1 1 d . . . C14 C 0.1974(6) -0.4551(2) -0.12067(17) 0.0383(8) Uani 1 1 d . . . C15 C 0.4491(6) 0.2307(2) 0.27477(16) 0.0358(7) Uani 1 1 d . . . N1 N 0.3230(5) -0.12742(17) 0.05466(13) 0.0306(6) Uani 1 1 d . . . O1 O -0.0983(3) -0.09767(13) 0.06890(10) 0.0292(5) Uani 1 1 d . . . F1 F 0.0989(4) -0.43975(14) -0.19106(10) 0.0636(7) Uani 1 1 d . . . F2 F 0.4170(4) -0.50029(15) -0.12381(13) 0.0685(7) Uani 1 1 d . . . F3 F 0.0414(5) -0.51582(14) -0.09347(12) 0.0697(7) Uani 1 1 d . . . F4A F 0.425(2) 0.2122(4) 0.3466(2) 0.061(3) Uani 0.473(14) 1 d P A 1 F5A F 0.320(2) 0.3044(5) 0.2601(5) 0.088(5) Uani 0.473(14) 1 d P A 1 F6A F 0.6981(14) 0.2546(8) 0.2806(7) 0.095(6) Uani 0.473(14) 1 d P A 1 F4B F 0.515(2) 0.3041(4) 0.2369(3) 0.075(3) Uani 0.527(14) 1 d P A 2 F5B F 0.641(2) 0.2110(4) 0.3210(5) 0.099(5) Uani 0.527(14) 1 d P A 2 F6B F 0.2596(13) 0.2625(6) 0.3070(6) 0.094(5) Uani 0.527(14) 1 d P A 2 H1 H 0.466(8) -0.098(3) 0.077(2) 0.075(13) Uiso 1 1 d . . . H2 H -0.040(6) -0.021(2) 0.1981(16) 0.038(9) Uiso 1 1 d . . . H3 H 0.074(5) 0.1071(19) 0.2798(16) 0.033(8) Uiso 1 1 d . . . H5 H 0.643(5) 0.1692(19) 0.1563(14) 0.021(7) Uiso 1 1 d . . . H6 H 0.536(5) 0.0435(19) 0.0794(16) 0.031(8) Uiso 1 1 d . . . H8 H -0.065(6) -0.179(2) -0.0470(15) 0.033(8) Uiso 1 1 d . . . H9 H -0.112(5) -0.3112(19) -0.1203(15) 0.028(7) Uiso 1 1 d . . . H11 H 0.591(6) -0.401(2) -0.0198(15) 0.034(8) Uiso 1 1 d . . . H12 H 0.629(6) -0.266(2) 0.0559(16) 0.035(8) 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 C1 0.0355(17) 0.0216(15) 0.0245(14) 0.0013(12) -0.0005(12) 0.0015(13) C2 0.0294(16) 0.0229(15) 0.0303(15) 0.0033(12) 0.0012(13) -0.0017(13) C3 0.0298(16) 0.0248(15) 0.0245(14) 0.0018(12) 0.0050(12) 0.0041(12) C4 0.0302(16) 0.0213(15) 0.0244(14) -0.0010(11) 0.0026(12) 0.0025(12) C5 0.0263(16) 0.0315(17) 0.0309(15) 0.0041(13) 0.0056(13) -0.0019(14) C6 0.0356(17) 0.0303(16) 0.0223(14) -0.0010(12) 0.0056(13) 0.0095(14) C7 0.0358(17) 0.0259(15) 0.0185(13) -0.0018(11) 0.0036(12) -0.0064(13) C8 0.0331(17) 0.0277(17) 0.0322(16) 0.0015(13) 0.0080(13) 0.0082(14) C9 0.0258(16) 0.0329(17) 0.0254(14) -0.0018(12) -0.0007(12) -0.0029(13) C10 0.0293(15) 0.0259(16) 0.0227(13) -0.0035(12) 0.0051(11) -0.0015(12) C11 0.0290(16) 0.0305(17) 0.0337(15) -0.0016(13) 0.0007(13) 0.0026(14) C12 0.0322(17) 0.0311(17) 0.0290(15) 0.0012(13) -0.0027(13) 0.0000(14) C13 0.0306(17) 0.0305(17) 0.0303(15) 0.0100(13) 0.0058(13) 0.0043(13) C14 0.0418(19) 0.0351(19) 0.0384(18) -0.0089(15) 0.0067(14) -0.0003(15) C15 0.0408(19) 0.0318(19) 0.0343(17) -0.0045(14) 0.0037(15) -0.0025(15) N1 0.0256(14) 0.0341(15) 0.0317(13) 0.0012(11) 0.0026(11) -0.0004(12) O1 0.0153(10) 0.0335(12) 0.0390(11) -0.0072(9) 0.0043(8) -0.0014(8) F1 0.0952(17) 0.0495(13) 0.0405(11) -0.0176(9) -0.0125(11) -0.0010(12) F2 0.0603(14) 0.0631(15) 0.0809(16) -0.0367(12) 0.0050(12) 0.0209(11) F3 0.0949(18) 0.0402(12) 0.0800(16) -0.0233(11) 0.0344(14) -0.0301(12) F4A 0.113(8) 0.044(3) 0.026(2) -0.013(2) 0.008(3) -0.015(4) F5A 0.130(11) 0.038(4) 0.076(6) -0.024(4) -0.062(6) 0.043(5) F6A 0.049(5) 0.101(9) 0.143(10) -0.092(8) 0.044(6) -0.049(6) F4B 0.134(8) 0.031(3) 0.061(3) -0.010(2) 0.018(4) -0.037(4) F5B 0.112(10) 0.058(4) 0.101(7) -0.031(4) -0.085(7) 0.021(4) F6B 0.074(5) 0.089(7) 0.130(9) -0.081(7) 0.060(6) -0.030(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C2 1.387(4) . ? C1 C6 1.388(4) . ? C1 C13 1.509(4) . ? C2 C3 1.376(4) . ? C2 H2 0.95(3) . ? C3 C4 1.387(4) . ? C3 H3 0.98(3) . ? C4 C5 1.380(4) . ? C4 C15 1.494(4) . ? C5 C6 1.391(4) . ? C5 H5 0.91(3) . ? C6 H6 0.96(3) . ? C7 C12 1.374(4) . ? C7 C8 1.395(4) . ? C7 N1 1.432(3) . ? C8 C9 1.382(4) . ? C8 H8 0.89(3) . ? C9 C10 1.388(4) . ? C9 H9 0.96(3) . ? C10 C11 1.385(4) . ? C10 C14 1.487(4) . ? C11 C12 1.376(4) . ? C11 H11 1.00(3) . ? C12 H12 1.01(3) . ? C13 O1 1.237(3) . ? C13 N1 1.346(4) . ? C14 F2 1.322(4) . ? C14 F3 1.330(4) . ? C14 F1 1.335(4) . ? C15 F5B 1.254(6) . ? C15 F5A 1.264(6) . ? C15 F6B 1.293(5) . ? C15 F4B 1.330(5) . ? C15 F6A 1.331(6) . ? C15 F4A 1.355(5) . ? N1 H1 0.90(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 C2 C1 C6 119.2(3) . . ? C2 C1 C13 117.0(3) . . ? C6 C1 C13 123.7(2) . . ? C3 C2 C1 120.7(3) . . ? C3 C2 H2 123.2(18) . . ? C1 C2 H2 116.1(18) . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.5(16) . . ? C4 C3 H3 119.6(16) . . ? C5 C4 C3 120.3(3) . . ? C5 C4 C15 120.0(3) . . ? C3 C4 C15 119.6(2) . . ? C4 C5 C6 119.6(3) . . ? C4 C5 H5 120.9(17) . . ? C6 C5 H5 119.5(16) . . ? C1 C6 C5 120.3(3) . . ? C1 C6 H6 120.0(17) . . ? C5 C6 H6 119.6(17) . . ? C12 C7 C8 120.3(3) . . ? C12 C7 N1 117.0(2) . . ? C8 C7 N1 122.7(3) . . ? C9 C8 C7 119.5(3) . . ? C9 C8 H8 119.6(19) . . ? C7 C8 H8 120.9(19) . . ? C8 C9 C10 120.1(3) . . ? C8 C9 H9 121.1(17) . . ? C10 C9 H9 118.7(17) . . ? C11 C10 C9 119.7(3) . . ? C11 C10 C14 120.6(3) . . ? C9 C10 C14 119.7(3) . . ? C12 C11 C10 120.4(3) . . ? C12 C11 H11 119.1(16) . . ? C10 C11 H11 120.5(16) . . ? C7 C12 C11 120.1(3) . . ? C7 C12 H12 119.1(16) . . ? C11 C12 H12 120.8(16) . . ? O1 C13 N1 123.8(3) . . ? O1 C13 C1 121.7(3) . . ? N1 C13 C1 114.4(3) . . ? F2 C14 F3 105.4(3) . . ? F2 C14 F1 105.5(2) . . ? F3 C14 F1 106.7(3) . . ? F2 C14 C10 113.5(3) . . ? F3 C14 C10 112.4(2) . . ? F1 C14 C10 112.6(3) . . ? F5B C15 F5A 133.4(4) . . ? F5B C15 F6B 111.4(6) . . ? F5B C15 F4B 106.9(5) . . ? F6B C15 F4B 102.4(5) . . ? F5A C15 F6A 106.5(6) . . ? F6B C15 F6A 131.5(4) . . ? F5A C15 F4A 104.9(5) . . ? F4B C15 F4A 135.8(4) . . ? F6A C15 F4A 100.4(5) . . ? F5B C15 C4 111.3(3) . . ? F5A C15 C4 115.1(3) . . ? F6B C15 C4 113.2(3) . . ? F4B C15 C4 111.0(3) . . ? F6A C15 C4 115.2(4) . . ? F4A C15 C4 113.1(3) . . ? C13 N1 C7 124.5(3) . . ? C13 N1 H1 101(3) . . ? C7 N1 H1 134(3) . . ? 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 C6 C1 C2 C3 0.0(4) . . . . ? C13 C1 C2 C3 -177.7(2) . . . . ? C1 C2 C3 C4 1.0(4) . . . . ? C2 C3 C4 C5 -0.7(4) . . . . ? C2 C3 C4 C15 -179.9(3) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C15 C4 C5 C6 178.5(3) . . . . ? C2 C1 C6 C5 -1.4(4) . . . . ? C13 C1 C6 C5 176.2(3) . . . . ? C4 C5 C6 C1 1.7(4) . . . . ? C12 C7 C8 C9 0.5(4) . . . . ? N1 C7 C8 C9 177.6(2) . . . . ? C7 C8 C9 C10 -0.2(4) . . . . ? C8 C9 C10 C11 0.3(4) . . . . ? C8 C9 C10 C14 177.7(3) . . . . ? C9 C10 C11 C12 -0.6(4) . . . . ? C14 C10 C11 C12 -178.0(3) . . . . ? C8 C7 C12 C11 -0.8(4) . . . . ? N1 C7 C12 C11 -178.1(2) . . . . ? C10 C11 C12 C7 0.9(4) . . . . ? C2 C1 C13 O1 33.9(4) . . . . ? C6 C1 C13 O1 -143.8(3) . . . . ? C2 C1 C13 N1 -146.1(3) . . . . ? C6 C1 C13 N1 36.3(4) . . . . ? C11 C10 C14 F2 -19.8(4) . . . . ? C9 C10 C14 F2 162.8(3) . . . . ? C11 C10 C14 F3 99.7(3) . . . . ? C9 C10 C14 F3 -77.7(3) . . . . ? C11 C10 C14 F1 -139.7(3) . . . . ? C9 C10 C14 F1 42.9(4) . . . . ? C5 C4 C15 F5B -78.9(8) . . . . ? C3 C4 C15 F5B 100.2(8) . . . . ? C5 C4 C15 F5A 97.2(9) . . . . ? C3 C4 C15 F5A -83.6(9) . . . . ? C5 C4 C15 F6B 154.7(7) . . . . ? C3 C4 C15 F6B -26.2(8) . . . . ? C5 C4 C15 F4B 40.1(7) . . . . ? C3 C4 C15 F4B -140.7(6) . . . . ? C5 C4 C15 F6A -27.4(9) . . . . ? C3 C4 C15 F6A 151.8(8) . . . . ? C5 C4 C15 F4A -142.2(6) . . . . ? C3 C4 C15 F4A 37.0(7) . . . . ? O1 C13 N1 C7 -4.1(4) . . . . ? C1 C13 N1 C7 175.9(2) . . . . ? C12 C7 N1 C13 -147.3(3) . . . . ? C8 C7 N1 C13 35.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.602 _refine_diff_density_min -0.295 _refine_diff_density_rms 0.059 # Attachment 't-1-1.cif' data_T-1-1 _database_code_depnum_ccdc_archive 'CCDC 843875' #TrackingRef 't-1-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H9 F6 N O' _chemical_formula_sum 'C15 H9 F6 N O' _chemical_formula_weight 333.23 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 2/c' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.2145(13) _cell_length_b 6.7790(3) _cell_length_c 9.7179(5) _cell_angle_alpha 90 _cell_angle_beta 100.886(5) _cell_angle_gamma 90 _cell_volume 1372.41(13) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 908 _cell_measurement_theta_min 1.6 _cell_measurement_theta_max 25.7 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9342 _exptl_absorpt_correction_T_max 0.9888 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7914 _diffrn_reflns_av_R_equivalents 0.0448 _diffrn_reflns_av_sigmaI/netI 0.0368 _diffrn_reflns_limit_h_min -28 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 29.27 _reflns_number_total 1717 _reflns_number_gt 1242 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; The nitrogen and oxygen atoms have been refined using ISOR command in SHELXL97. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.8990P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1717 _refine_ls_number_parameters 166 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0730 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1282 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instructions_details ; TITL T-1-1 in C 1 2/c 1 CELL 0.71073 21.2145 6.7790 9.7179 90.000 100.886 90.000 ZERR 4 0.0013 0.0003 0.0005 0.000 0.005 0.000 LATT 7 SYMM -X,Y, 0.50000-Z SFAC C H N O F UNIT 60 36 4 4 24 MERG 2 TEMP -153 L.S. 12 ACTA 50 CONF BOND $H HTAB FMAP 2 PLAN 10 ISOR 0.01 0.02 N1 C8 WGHT 0.053100 0.899000 FVAR 5.09862 0.63564 C1 1 0.129307 0.188725 0.577008 11.00000 0.02997 0.04236 = 0.02210 -0.00519 0.00773 0.00041 C2 1 0.170417 0.334172 0.543903 11.00000 0.02914 0.05067 = 0.03939 -0.01004 0.00670 -0.00736 C3 1 0.147488 0.482737 0.450604 11.00000 0.04477 0.04200 = 0.04527 -0.00545 0.01605 -0.01522 C4 1 0.083429 0.487986 0.388595 11.00000 0.04918 0.03719 = 0.03429 0.00145 0.01323 -0.00412 C5 1 0.041987 0.344092 0.421147 11.00000 0.03235 0.03890 = 0.02560 -0.00027 0.00638 0.00053 C6 1 0.064300 0.194482 0.515291 11.00000 0.02922 0.03509 = 0.02095 -0.00281 0.00921 -0.00213 C7 1 0.156454 0.029111 0.676440 11.00000 0.03074 0.05015 = 0.03305 -0.00053 0.00516 0.00398 C8 1 0.017252 0.055941 0.563307 10.50000 0.01505 0.02335 = 0.02245 0.00531 0.00255 -0.00247 N1 3 0.019066 0.048033 0.538413 10.50000 0.03823 0.05414 = 0.01940 0.00268 0.01037 0.00167 O1 4 0.012638 0.052590 0.689325 10.50000 0.03919 0.04522 = 0.01828 -0.00301 0.01121 -0.00553 part 1 F1A 5 0.219200 -0.007297 0.673071 21.00000 0.03968 0.12567 = 0.09141 0.03816 0.01856 0.03500 F2A 5 0.157045 0.071880 0.809913 21.00000 0.07715 0.06491 = 0.02773 0.00035 0.00506 0.00296 F3A 5 0.129587 -0.147550 0.648162 21.00000 0.05207 0.04163 = 0.07419 0.00024 -0.01768 0.00817 part 2 F1B 5 0.216724 0.047541 0.719943 -21.00000 0.01959 0.08810 = 0.12534 0.06095 -0.01368 -0.00606 F2B 5 0.127505 0.030878 0.791247 -21.00000 0.05815 0.07383 = 0.03097 0.02079 0.01593 0.01228 F3B 5 0.141999 -0.140405 0.628683 -21.00000 0.19636 0.03735 = 0.06092 0.00570 -0.00908 0.01477 part 0 H1 2 0.012144 0.015995 0.628062 10.50000 0.01482 H2 2 0.214665 0.326280 0.588226 11.00000 0.04501 H3 2 0.176192 0.583979 0.430967 11.00000 0.04076 H4 2 0.066902 0.595876 0.325610 11.00000 0.05184 H5 2 -0.002609 0.348663 0.381370 11.00000 0.03988 HKLF 4 END ; 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.12931(8) 0.1887(3) 0.57701(16) 0.0311(4) Uani 1 1 d . A . C2 C 0.17042(9) 0.3342(3) 0.5439(2) 0.0397(4) Uani 1 1 d . . . C3 C 0.14749(10) 0.4827(3) 0.4506(2) 0.0430(5) Uani 1 1 d . . . C4 C 0.08343(10) 0.4880(3) 0.3886(2) 0.0395(4) Uani 1 1 d . . . C5 C 0.04199(8) 0.3441(3) 0.42115(17) 0.0322(4) Uani 1 1 d . . . C6 C 0.06430(7) 0.1945(2) 0.51529(15) 0.0278(4) Uani 1 1 d . . . C7 C 0.15645(8) 0.0291(3) 0.67644(19) 0.0381(4) Uani 1 1 d . . . C8 C 0.0173(5) 0.0559(16) 0.5633(19) 0.0204(14) Uani 0.50 1 d PU . . N1 N 0.0191(6) 0.0480(18) 0.5384(14) 0.037(3) Uani 0.50 1 d PU . . O1 O 0.01264(12) 0.0526(4) 0.6893(3) 0.0335(6) Uani 0.50 1 d P . . F1A F 0.2192(3) -0.0073(15) 0.6731(9) 0.085(2) Uani 0.64(3) 1 d P A 1 F2A F 0.1570(6) 0.0719(7) 0.8099(3) 0.0572(17) Uani 0.64(3) 1 d P A 1 F3A F 0.1296(3) -0.1476(12) 0.6482(9) 0.0598(15) Uani 0.64(3) 1 d P A 1 F1B F 0.2167(5) 0.048(3) 0.720(2) 0.081(5) Uani 0.36(3) 1 d P A 2 F2B F 0.1275(8) 0.031(2) 0.7912(12) 0.053(3) Uani 0.36(3) 1 d P A 2 F3B F 0.1420(10) -0.140(2) 0.629(2) 0.103(5) Uani 0.36(3) 1 d P A 2 H1 H 0.012(2) 0.016(6) 0.628(5) 0.015(13) Uiso 0.50 1 d P . . H2 H 0.2147(11) 0.326(3) 0.588(2) 0.045(5) Uiso 1 1 d . . . H3 H 0.1762(10) 0.584(3) 0.431(2) 0.041(5) Uiso 1 1 d . . . H4 H 0.0669(10) 0.596(3) 0.326(2) 0.052(6) Uiso 1 1 d . . . H5 H -0.0026(10) 0.349(3) 0.381(2) 0.040(5) 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 C1 0.0300(8) 0.0424(9) 0.0221(7) -0.0052(7) 0.0077(6) 0.0004(7) C2 0.0291(9) 0.0507(11) 0.0394(10) -0.0100(8) 0.0067(7) -0.0074(8) C3 0.0448(11) 0.0420(10) 0.0453(11) -0.0055(8) 0.0160(9) -0.0152(8) C4 0.0492(11) 0.0372(10) 0.0343(9) 0.0015(8) 0.0132(8) -0.0041(8) C5 0.0323(9) 0.0389(9) 0.0256(8) -0.0003(7) 0.0064(7) 0.0005(7) C6 0.0292(8) 0.0351(9) 0.0210(7) -0.0028(6) 0.0092(6) -0.0021(6) C7 0.0307(9) 0.0502(11) 0.0331(9) -0.0005(8) 0.0052(7) 0.0040(8) C8 0.015(3) 0.023(3) 0.022(5) 0.005(3) 0.003(3) -0.0025(17) N1 0.038(4) 0.054(5) 0.019(4) 0.003(2) 0.010(2) 0.002(2) O1 0.0392(14) 0.0452(15) 0.0183(13) -0.0030(11) 0.0112(11) -0.0055(11) F1A 0.0397(19) 0.126(4) 0.091(3) 0.038(3) 0.019(2) 0.035(2) F2A 0.077(5) 0.0649(17) 0.0277(11) 0.0003(10) 0.0051(15) 0.003(2) F3A 0.052(3) 0.042(2) 0.074(4) 0.000(2) -0.0177(15) 0.0082(12) F1B 0.020(3) 0.088(6) 0.125(10) 0.061(6) -0.014(4) -0.006(3) F2B 0.058(5) 0.074(4) 0.031(3) 0.021(2) 0.016(3) 0.012(4) F3B 0.196(13) 0.037(4) 0.061(4) 0.006(3) -0.009(7) 0.015(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C1 C2 1.394(2) . ? C1 C6 1.397(2) . ? C1 C7 1.492(2) . ? C2 C3 1.381(3) . ? C2 H2 0.96(2) . ? C3 C4 1.379(3) . ? C3 H3 0.96(2) . ? C4 C5 1.389(2) . ? C4 H4 0.98(2) . ? C5 C6 1.388(2) . ? C5 H5 0.95(2) . ? C6 N1 1.428(12) . ? C6 C8 1.507(12) . ? C7 F3B 1.255(16) . ? C7 F1B 1.275(9) . ? C7 F2A 1.327(4) . ? C7 F3A 1.332(8) . ? C7 F1A 1.360(6) . ? C7 F2B 1.371(6) . ? C8 O1 1.247(19) . ? C8 H1 0.71(5) . ? N1 O1 1.499(14) . ? N1 H1 0.94(6) . ? 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 C2 C1 C6 119.43(16) . . ? C2 C1 C7 118.74(15) . . ? C6 C1 C7 121.83(15) . . ? C3 C2 C1 120.63(17) . . ? C3 C2 H2 122.0(12) . . ? C1 C2 H2 117.4(12) . . ? C4 C3 C2 120.11(17) . . ? C4 C3 H3 120.3(12) . . ? C2 C3 H3 119.6(12) . . ? C3 C4 C5 119.75(18) . . ? C3 C4 H4 120.1(12) . . ? C5 C4 H4 120.1(13) . . ? C6 C5 C4 120.77(17) . . ? C6 C5 H5 118.7(12) . . ? C4 C5 H5 120.5(11) . . ? C5 C6 C1 119.32(15) . . ? C5 C6 N1 117.1(5) . . ? C1 C6 N1 123.5(5) . . ? C5 C6 C8 119.7(5) . . ? C1 C6 C8 120.5(5) . . ? F3B C7 F1B 111.8(8) . . ? F3B C7 F2A 121.2(9) . . ? F1B C7 F2A 80.3(8) . . ? F1B C7 F3A 121.3(9) . . ? F2A C7 F3A 108.8(5) . . ? F3B C7 F1A 89.8(8) . . ? F2A C7 F1A 103.6(4) . . ? F3A C7 F1A 102.4(5) . . ? F3B C7 F2B 101.1(8) . . ? F1B C7 F2B 107.7(6) . . ? F3A C7 F2B 86.3(8) . . ? F1A C7 F2B 127.7(6) . . ? F3B C7 C1 112.8(7) . . ? F1B C7 C1 112.6(5) . . ? F2A C7 C1 113.9(2) . . ? F3A C7 C1 114.9(3) . . ? F1A C7 C1 112.1(3) . . ? F2B C7 C1 110.1(3) . . ? O1 C8 N1 125.2(5) . 5_556 ? O1 C8 C6 119.7(10) . . ? N1 C8 C6 115.0(9) 5_556 . ? O1 C8 C8 132.4(13) . 5_556 ? C6 C8 C8 107.9(16) . 5_556 ? N1 C8 H1 107(3) 5_556 . ? C6 C8 H1 137(4) . . ? C8 C8 H1 113(4) 5_556 . ? N1 N1 C6 132.9(17) 5_556 . ? C8 N1 C6 124.2(5) 5_556 . ? N1 N1 O1 116.7(15) 5_556 . ? C8 N1 O1 126.1(7) 5_556 . ? C6 N1 O1 109.1(8) . . ? N1 N1 H1 104(3) 5_556 . ? C8 N1 H1 113(3) 5_556 . ? C6 N1 H1 122(3) . . ? C8 O1 O1 162.0(6) . 2_556 ? O1 O1 N1 162.7(6) 2_556 . ? O1 O1 H1 148(4) 2_556 . ? 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 C6 C1 C2 C3 -0.2(3) . . . . ? C7 C1 C2 C3 178.93(16) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C2 C3 C4 C5 0.5(3) . . . . ? C3 C4 C5 C6 -0.1(3) . . . . ? C4 C5 C6 C1 -0.4(2) . . . . ? C4 C5 C6 N1 -177.5(6) . . . . ? C4 C5 C6 C8 172.0(8) . . . . ? C2 C1 C6 C5 0.6(2) . . . . ? C7 C1 C6 C5 -178.58(15) . . . . ? C2 C1 C6 N1 177.5(7) . . . . ? C7 C1 C6 N1 -1.7(7) . . . . ? C2 C1 C6 C8 -171.8(8) . . . . ? C7 C1 C6 C8 9.1(8) . . . . ? C2 C1 C7 F3B -127.8(13) . . . . ? C6 C1 C7 F3B 51.3(13) . . . . ? C2 C1 C7 F1B -0.1(14) . . . . ? C6 C1 C7 F1B 179.0(14) . . . . ? C2 C1 C7 F2A 88.9(7) . . . . ? C6 C1 C7 F2A -91.9(7) . . . . ? C2 C1 C7 F3A -144.5(4) . . . . ? C6 C1 C7 F3A 34.6(5) . . . . ? C2 C1 C7 F1A -28.3(5) . . . . ? C6 C1 C7 F1A 150.9(5) . . . . ? C2 C1 C7 F2B 120.1(10) . . . . ? C6 C1 C7 F2B -60.8(10) . . . . ? C5 C6 C8 O1 -116.4(8) . . . . ? C1 C6 C8 O1 56.0(11) . . . . ? N1 C6 C8 O1 167(6) . . . . ? C5 C6 C8 N1 60.3(6) . . . 5_556 ? C1 C6 C8 N1 -127.4(3) . . . 5_556 ? N1 C6 C8 N1 -17(5) . . . 5_556 ? C5 C6 C8 C8 63.0(13) . . . 5_556 ? C1 C6 C8 C8 -124.7(9) . . . 5_556 ? N1 C6 C8 C8 -14(4) . . . 5_556 ? C5 C6 N1 N1 48(2) . . . 5_556 ? C1 C6 N1 N1 -128(2) . . . 5_556 ? C8 C6 N1 N1 157(7) . . . 5_556 ? C5 C6 N1 C8 53.7(7) . . . 5_556 ? C1 C6 N1 C8 -123.3(5) . . . 5_556 ? C8 C6 N1 C8 162(6) . . . 5_556 ? C5 C6 N1 O1 -118.2(6) . . . . ? C1 C6 N1 O1 64.8(9) . . . . ? C8 C6 N1 O1 -10(5) . . . . ? N1 C8 O1 O1 -44.5(18) 5_556 . . 2_556 ? C6 C8 O1 O1 131.8(12) . . . 2_556 ? C8 C8 O1 O1 -47(3) 5_556 . . 2_556 ? N1 C8 O1 N1 66(24) 5_556 . . . ? C6 C8 O1 N1 -117(24) . . . . ? C8 C8 O1 N1 63(23) 5_556 . . . ? N1 N1 O1 C8 -110(25) 5_556 . . . ? C8 N1 O1 C8 -112(24) 5_556 . . . ? C6 N1 O1 C8 60(24) . . . . ? N1 N1 O1 O1 -33(3) 5_556 . . 2_556 ? C8 N1 O1 O1 -36(2) 5_556 . . 2_556 ? C6 N1 O1 O1 135.8(12) . . . 2_556 ? _diffrn_measured_fraction_theta_max 0.915 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.230 _refine_diff_density_min -0.237 _refine_diff_density_rms 0.045