# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_TDZ-1 _database_code_depnum_ccdc_archive 'CCDC 923893' #TrackingRef 'TDZ-1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H14 F N3 O2 S' _chemical_formula_sum 'C21 H14 F N3 O2 S' _chemical_formula_weight 391.41 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' S S 0.1246 0.1234 '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 20.6997(18) _cell_length_b 5.8050(6) _cell_length_c 30.904(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.387(6) _cell_angle_gamma 90.00 _cell_volume 3597.1(6) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1616 _exptl_absorpt_coefficient_mu 0.213 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9428 _exptl_absorpt_correction_T_max 0.9894 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 15884 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 27.94 _reflns_number_total 4254 _reflns_number_gt 3089 _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^)+(0.0508P)^2^+2.1486P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4254 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0746 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1224 _refine_ls_wR_factor_gt 0.1116 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL TDZ-2 in C2/c CELL 0.71073 20.6997 5.8050 30.9043 90.000 104.387 90.000 ZERR 8.00 0.0018 0.0006 0.0029 0.000 0.006 0.000 LATT 7 SYMM -X,Y, 0.50000-Z SFAC C H N O F S UNIT 168 112 24 16 8 8 MERG 2 L.S. 12 TEMP 21 SIZE 0.28 0.12 0.05 ACTA HTAB CONF BOND $H FMAP 2 PLAN 10 WGHT 0.050800 2.148600 FVAR 0.06718 S1 6 0.636133 0.052559 -0.001244 11.00000 0.04236 0.04538 = 0.05006 0.00615 0.01717 0.01589 F1 5 0.846215 0.141301 -0.134033 11.00000 0.05854 0.10012 = 0.07852 -0.01133 0.04065 0.00841 O1 4 0.769452 0.522706 -0.148009 11.00000 0.05295 0.07788 = 0.06499 0.01013 0.02061 -0.01231 O2 4 0.590090 -0.117786 0.063269 11.00000 0.06552 0.05958 = 0.07547 0.02065 0.03314 0.03034 N1 3 0.538652 0.211145 0.037021 11.00000 0.03875 0.04889 = 0.04692 0.00642 0.01753 0.01610 AFIX 43 H1N 2 0.507388 0.307457 0.037792 11.00000 -1.20000 AFIX 0 N2 3 0.567424 0.422048 -0.019588 11.00000 0.04723 0.05048 = 0.05324 0.01104 0.02298 0.01940 N3 3 0.611494 0.423934 -0.046557 11.00000 0.04919 0.05387 = 0.05440 0.01130 0.02461 0.01919 C1 1 0.624669 0.677474 -0.262616 11.00000 0.08905 0.12603 = 0.06947 0.03087 0.02472 0.01665 AFIX 43 H1 2 0.592683 0.713292 -0.288667 11.00000 -1.20000 AFIX 0 C2 1 0.676607 0.822844 -0.246509 11.00000 0.12286 0.07363 = 0.07866 0.02926 0.05529 0.02178 AFIX 43 H2 2 0.679862 0.958936 -0.261704 11.00000 -1.20000 AFIX 0 C3 1 0.724743 0.771379 -0.207823 11.00000 0.09030 0.06098 = 0.07470 0.00019 0.04566 -0.00726 AFIX 43 H3 2 0.760365 0.870812 -0.197140 11.00000 -1.20000 AFIX 0 C4 1 0.718871 0.570583 -0.185517 11.00000 0.05668 0.05586 = 0.05176 0.00127 0.02963 0.00293 C5 1 0.666968 0.424220 -0.201466 11.00000 0.07203 0.06883 = 0.05989 0.01284 0.01595 -0.00856 AFIX 43 H5 2 0.663230 0.288310 -0.186341 11.00000 -1.20000 AFIX 0 C6 1 0.620080 0.479070 -0.240156 11.00000 0.08685 0.12236 = 0.06407 0.02511 0.00700 -0.01819 AFIX 43 H6 2 0.584731 0.378905 -0.251098 11.00000 -1.20000 AFIX 0 C7 1 0.758445 0.355441 -0.118877 11.00000 0.04172 0.06082 = 0.04683 -0.00109 0.01434 -0.00365 C8 1 0.798483 0.162993 -0.111234 11.00000 0.03959 0.07038 = 0.05156 -0.01259 0.01823 0.00352 C9 1 0.791603 -0.004319 -0.081975 11.00000 0.05110 0.05955 = 0.06405 -0.00537 0.01936 0.02091 AFIX 43 H9 2 0.819364 -0.132661 -0.077508 11.00000 -1.20000 AFIX 0 C10 1 0.742542 0.019475 -0.058907 11.00000 0.05068 0.05179 = 0.05189 0.00496 0.01843 0.01464 AFIX 43 H10 2 0.737002 -0.094518 -0.038992 11.00000 -1.20000 AFIX 0 C11 1 0.701585 0.212231 -0.065300 11.00000 0.03639 0.04822 = 0.04001 -0.00310 0.00937 0.00813 C12 1 0.710396 0.380333 -0.095219 11.00000 0.04055 0.04960 = 0.05110 0.00136 0.01213 0.00679 AFIX 43 H12 2 0.683648 0.511209 -0.099387 11.00000 -1.20000 AFIX 0 C13 1 0.649938 0.244635 -0.040675 11.00000 0.03807 0.04379 = 0.04056 0.00006 0.01026 0.00760 C14 1 0.575430 0.241982 0.006009 11.00000 0.03635 0.04159 = 0.04273 0.00095 0.01082 0.01161 C15 1 0.550340 0.031753 0.066680 11.00000 0.03762 0.04767 = 0.04913 0.00650 0.00954 0.00892 C16 1 0.514783 0.026174 0.102877 11.00000 0.03768 0.05003 = 0.04419 0.00647 0.00904 0.00479 C17 1 0.522541 -0.165916 0.129491 11.00000 0.10462 0.06648 = 0.08074 0.02405 0.04670 0.02438 AFIX 43 H17 2 0.548878 -0.287384 0.124228 11.00000 -1.20000 AFIX 0 C18 1 0.491443 -0.179687 0.164031 11.00000 0.13539 0.08081 = 0.08412 0.03125 0.05285 0.01047 AFIX 43 H18 2 0.496336 -0.312040 0.181501 11.00000 -1.20000 AFIX 0 C19 1 0.454056 -0.004072 0.172833 11.00000 0.07118 0.09253 = 0.05940 0.00812 0.02873 -0.00695 AFIX 43 H19 2 0.434611 -0.012417 0.196872 11.00000 -1.20000 AFIX 0 C20 1 0.445251 0.182499 0.146557 11.00000 0.08375 0.10255 = 0.06878 0.01691 0.03936 0.03973 AFIX 43 H20 2 0.418456 0.302369 0.151915 11.00000 -1.20000 AFIX 0 C21 1 0.475670 0.198938 0.111420 11.00000 0.08343 0.08519 = 0.06335 0.02825 0.03810 0.04244 AFIX 43 H21 2 0.469155 0.329921 0.093531 11.00000 -1.20000 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 S1 S 0.63613(2) 0.05256(9) -0.001244(16) 0.04493(16) Uani 1 1 d . . . F1 F 0.84622(6) 0.1413(3) -0.13403(4) 0.0749(4) Uani 1 1 d . . . O1 O 0.76945(7) 0.5227(3) -0.14801(5) 0.0642(4) Uani 1 1 d . . . O2 O 0.59009(7) -0.1178(3) 0.06327(5) 0.0641(4) Uani 1 1 d . . . N1 N 0.53865(7) 0.2111(3) 0.03702(5) 0.0436(4) Uani 1 1 d . . . H1N H 0.5074 0.3075 0.0378 0.052 Uiso 1 1 calc R . . N2 N 0.56742(8) 0.4220(3) -0.01959(5) 0.0485(4) Uani 1 1 d . . . N3 N 0.61149(8) 0.4239(3) -0.04656(5) 0.0504(4) Uani 1 1 d . . . C1 C 0.62467(16) 0.6775(7) -0.26262(10) 0.0940(10) Uani 1 1 d . . . H1 H 0.5927 0.7133 -0.2887 0.113 Uiso 1 1 calc R . . C2 C 0.67661(17) 0.8228(6) -0.24651(10) 0.0864(9) Uani 1 1 d . . . H2 H 0.6799 0.9589 -0.2617 0.104 Uiso 1 1 calc R . . C3 C 0.72474(14) 0.7714(5) -0.20782(8) 0.0709(7) Uani 1 1 d . . . H3 H 0.7604 0.8708 -0.1971 0.085 Uiso 1 1 calc R . . C4 C 0.71887(10) 0.5706(4) -0.18552(7) 0.0519(5) Uani 1 1 d . . . C5 C 0.66697(12) 0.4242(5) -0.20147(8) 0.0670(7) Uani 1 1 d . . . H5 H 0.6632 0.2883 -0.1863 0.080 Uiso 1 1 calc R . . C6 C 0.62008(15) 0.4791(6) -0.24016(9) 0.0932(10) Uani 1 1 d . . . H6 H 0.5847 0.3789 -0.2511 0.112 Uiso 1 1 calc R . . C7 C 0.75845(9) 0.3554(4) -0.11888(6) 0.0492(5) Uani 1 1 d . . . C8 C 0.79848(9) 0.1630(4) -0.11123(7) 0.0526(5) Uani 1 1 d . . . C9 C 0.79160(10) -0.0043(4) -0.08197(7) 0.0573(6) Uani 1 1 d . . . H9 H 0.8194 -0.1327 -0.0775 0.069 Uiso 1 1 calc R . . C10 C 0.74254(9) 0.0195(4) -0.05891(7) 0.0504(5) Uani 1 1 d . . . H10 H 0.7370 -0.0945 -0.0390 0.061 Uiso 1 1 calc R . . C11 C 0.70158(8) 0.2122(4) -0.06530(6) 0.0416(4) Uani 1 1 d . . . C12 C 0.71040(9) 0.3803(4) -0.09522(6) 0.0470(5) Uani 1 1 d . . . H12 H 0.6836 0.5112 -0.0994 0.056 Uiso 1 1 calc R . . C13 C 0.64994(9) 0.2446(3) -0.04068(6) 0.0407(4) Uani 1 1 d . . . C14 C 0.57543(8) 0.2420(3) 0.00601(6) 0.0400(4) Uani 1 1 d . . . C15 C 0.55034(9) 0.0318(4) 0.06668(6) 0.0450(5) Uani 1 1 d . . . C16 C 0.51478(9) 0.0262(4) 0.10288(6) 0.0442(5) Uani 1 1 d . . . C17 C 0.52254(14) -0.1659(5) 0.12949(9) 0.0798(8) Uani 1 1 d . . . H17 H 0.5489 -0.2874 0.1242 0.096 Uiso 1 1 calc R . . C18 C 0.49144(17) -0.1797(6) 0.16403(10) 0.0956(10) Uani 1 1 d . . . H18 H 0.4963 -0.3120 0.1815 0.115 Uiso 1 1 calc R . . C19 C 0.45406(12) -0.0041(5) 0.17283(8) 0.0722(7) Uani 1 1 d . . . H19 H 0.4346 -0.0124 0.1969 0.087 Uiso 1 1 calc R . . C20 C 0.44525(13) 0.1825(6) 0.14656(8) 0.0814(8) Uani 1 1 d . . . H20 H 0.4185 0.3024 0.1519 0.098 Uiso 1 1 calc R . . C21 C 0.47567(12) 0.1989(5) 0.11142(8) 0.0738(8) Uani 1 1 d . . . H21 H 0.4692 0.3299 0.0935 0.089 Uiso 1 1 calc R . . 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 S1 0.0424(3) 0.0454(3) 0.0501(3) 0.0062(2) 0.0172(2) 0.0159(2) F1 0.0585(7) 0.1001(12) 0.0785(9) -0.0113(8) 0.0407(7) 0.0084(7) O1 0.0529(8) 0.0779(12) 0.0650(9) 0.0101(8) 0.0206(7) -0.0123(8) O2 0.0655(9) 0.0596(10) 0.0755(10) 0.0206(8) 0.0331(8) 0.0303(8) N1 0.0388(8) 0.0489(11) 0.0469(9) 0.0064(8) 0.0175(7) 0.0161(7) N2 0.0472(9) 0.0505(11) 0.0532(9) 0.0110(8) 0.0230(7) 0.0194(8) N3 0.0492(9) 0.0539(12) 0.0544(10) 0.0113(8) 0.0246(8) 0.0192(8) C1 0.089(2) 0.126(3) 0.0695(17) 0.0309(19) 0.0247(15) 0.017(2) C2 0.123(2) 0.074(2) 0.0787(18) 0.0293(16) 0.0553(18) 0.0218(19) C3 0.0903(18) 0.0610(17) 0.0747(16) 0.0002(13) 0.0457(14) -0.0073(14) C4 0.0567(12) 0.0559(15) 0.0518(11) 0.0013(10) 0.0296(10) 0.0029(10) C5 0.0720(15) 0.0688(18) 0.0599(14) 0.0128(12) 0.0159(12) -0.0086(13) C6 0.0869(19) 0.122(3) 0.0641(16) 0.0251(17) 0.0070(14) -0.0182(18) C7 0.0417(10) 0.0608(14) 0.0468(10) -0.0011(10) 0.0143(8) -0.0036(10) C8 0.0396(10) 0.0704(16) 0.0516(11) -0.0126(11) 0.0182(9) 0.0035(10) C9 0.0511(12) 0.0596(15) 0.0641(13) -0.0054(11) 0.0194(10) 0.0209(11) C10 0.0507(11) 0.0518(14) 0.0519(11) 0.0050(10) 0.0184(9) 0.0146(10) C11 0.0364(9) 0.0482(12) 0.0400(9) -0.0031(9) 0.0094(7) 0.0081(8) C12 0.0406(10) 0.0496(13) 0.0511(11) 0.0014(10) 0.0121(8) 0.0068(9) C13 0.0381(9) 0.0438(12) 0.0406(9) 0.0001(8) 0.0103(7) 0.0076(8) C14 0.0363(9) 0.0416(12) 0.0427(9) 0.0009(9) 0.0108(7) 0.0116(8) C15 0.0376(9) 0.0477(13) 0.0491(10) 0.0065(9) 0.0095(8) 0.0089(9) C16 0.0377(9) 0.0500(13) 0.0442(10) 0.0065(9) 0.0090(8) 0.0048(9) C17 0.105(2) 0.0665(19) 0.0807(17) 0.0241(15) 0.0467(15) 0.0244(16) C18 0.135(3) 0.081(2) 0.0841(19) 0.0313(17) 0.0528(19) 0.010(2) C19 0.0712(16) 0.093(2) 0.0594(14) 0.0081(14) 0.0287(12) -0.0070(15) C20 0.0837(17) 0.103(2) 0.0688(15) 0.0169(16) 0.0394(13) 0.0397(16) C21 0.0834(16) 0.085(2) 0.0633(14) 0.0283(13) 0.0381(12) 0.0424(15) _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 S1 C14 1.7257(18) . ? S1 C13 1.727(2) . ? F1 C8 1.354(2) . ? O1 C7 1.381(3) . ? O1 C4 1.383(2) . ? O2 C15 1.219(2) . ? N1 C15 1.369(2) . ? N1 C14 1.376(2) . ? N1 H1N 0.8600 . ? N2 C14 1.296(2) . ? N2 N3 1.380(2) . ? N3 C13 1.295(2) . ? C1 C2 1.360(4) . ? C1 C6 1.360(4) . ? C1 H1 0.9300 . ? C2 C3 1.385(4) . ? C2 H2 0.9300 . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.362(3) . ? C5 C6 1.377(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C8 1.376(3) . ? C7 C12 1.381(3) . ? C8 C9 1.358(3) . ? C9 C10 1.385(3) . ? C9 H9 0.9300 . ? C10 C11 1.388(3) . ? C10 H10 0.9300 . ? C11 C12 1.387(3) . ? C11 C13 1.470(2) . ? C12 H12 0.9300 . ? C15 C16 1.484(3) . ? C16 C21 1.355(3) . ? C16 C17 1.371(3) . ? C17 C18 1.379(4) . ? C17 H17 0.9300 . ? C18 C19 1.348(4) . ? C18 H18 0.9300 . ? C19 C20 1.339(4) . ? C19 H19 0.9300 . ? C20 C21 1.387(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? 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 C14 S1 C13 86.20(9) . . ? C7 O1 C4 118.32(16) . . ? C15 N1 C14 121.95(15) . . ? C15 N1 H1N 119.0 . . ? C14 N1 H1N 119.0 . . ? C14 N2 N3 111.80(15) . . ? C13 N3 N2 112.59(16) . . ? C2 C1 C6 119.2(3) . . ? C2 C1 H1 120.4 . . ? C6 C1 H1 120.4 . . ? C1 C2 C3 121.0(3) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 118.8(3) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C5 C4 C3 120.5(2) . . ? C5 C4 O1 122.9(2) . . ? C3 C4 O1 116.6(2) . . ? C4 C5 C6 119.5(2) . . ? C4 C5 H5 120.3 . . ? C6 C5 H5 120.3 . . ? C1 C6 C5 121.0(3) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C8 C7 C12 118.5(2) . . ? C8 C7 O1 119.53(18) . . ? C12 C7 O1 121.9(2) . . ? F1 C8 C9 119.4(2) . . ? F1 C8 C7 118.2(2) . . ? C9 C8 C7 122.44(18) . . ? C8 C9 C10 118.9(2) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C9 C10 C11 120.5(2) . . ? C9 C10 H10 119.8 . . ? C11 C10 H10 119.8 . . ? C12 C11 C10 119.02(17) . . ? C12 C11 C13 119.21(17) . . ? C10 C11 C13 121.76(18) . . ? C7 C12 C11 120.71(19) . . ? C7 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? N3 C13 C11 122.04(18) . . ? N3 C13 S1 114.47(14) . . ? C11 C13 S1 123.48(14) . . ? N2 C14 N1 121.40(16) . . ? N2 C14 S1 114.92(14) . . ? N1 C14 S1 123.67(14) . . ? O2 C15 N1 119.67(18) . . ? O2 C15 C16 121.44(18) . . ? N1 C15 C16 118.89(17) . . ? C21 C16 C17 118.1(2) . . ? C21 C16 C15 124.24(19) . . ? C17 C16 C15 117.6(2) . . ? C16 C17 C18 120.3(3) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 120.9(3) . . ? C19 C18 H18 119.5 . . ? C17 C18 H18 119.5 . . ? C20 C19 C18 119.2(2) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? C19 C20 C21 120.7(3) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C16 C21 C20 120.7(2) . . ? C16 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? 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 C14 N2 N3 C13 1.0(2) . . . . ? C6 C1 C2 C3 0.2(5) . . . . ? C1 C2 C3 C4 -0.6(4) . . . . ? C2 C3 C4 C5 0.6(4) . . . . ? C2 C3 C4 O1 177.7(2) . . . . ? C7 O1 C4 C5 -18.1(3) . . . . ? C7 O1 C4 C3 164.91(19) . . . . ? C3 C4 C5 C6 -0.2(4) . . . . ? O1 C4 C5 C6 -177.1(2) . . . . ? C2 C1 C6 C5 0.2(5) . . . . ? C4 C5 C6 C1 -0.2(5) . . . . ? C4 O1 C7 C8 119.0(2) . . . . ? C4 O1 C7 C12 -64.4(3) . . . . ? C12 C7 C8 F1 -178.99(17) . . . . ? O1 C7 C8 F1 -2.2(3) . . . . ? C12 C7 C8 C9 1.2(3) . . . . ? O1 C7 C8 C9 177.94(19) . . . . ? F1 C8 C9 C10 -179.88(18) . . . . ? C7 C8 C9 C10 -0.1(3) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? C9 C10 C11 C12 0.2(3) . . . . ? C9 C10 C11 C13 -178.79(18) . . . . ? C8 C7 C12 C11 -1.6(3) . . . . ? O1 C7 C12 C11 -178.30(18) . . . . ? C10 C11 C12 C7 1.0(3) . . . . ? C13 C11 C12 C7 179.97(17) . . . . ? N2 N3 C13 C11 -178.92(16) . . . . ? N2 N3 C13 S1 0.1(2) . . . . ? C12 C11 C13 N3 1.2(3) . . . . ? C10 C11 C13 N3 -179.87(18) . . . . ? C12 C11 C13 S1 -177.75(14) . . . . ? C10 C11 C13 S1 1.2(3) . . . . ? C14 S1 C13 N3 -0.79(15) . . . . ? C14 S1 C13 C11 178.20(16) . . . . ? N3 N2 C14 N1 177.01(16) . . . . ? N3 N2 C14 S1 -1.6(2) . . . . ? C15 N1 C14 N2 -174.59(18) . . . . ? C15 N1 C14 S1 3.9(3) . . . . ? C13 S1 C14 N2 1.38(15) . . . . ? C13 S1 C14 N1 -177.21(17) . . . . ? C14 N1 C15 O2 -6.9(3) . . . . ? C14 N1 C15 C16 172.19(17) . . . . ? O2 C15 C16 C21 172.5(2) . . . . ? N1 C15 C16 C21 -6.5(3) . . . . ? O2 C15 C16 C17 -7.0(3) . . . . ? N1 C15 C16 C17 174.0(2) . . . . ? C21 C16 C17 C18 -0.4(4) . . . . ? C15 C16 C17 C18 179.1(2) . . . . ? C16 C17 C18 C19 -1.3(5) . . . . ? C17 C18 C19 C20 2.4(5) . . . . ? C18 C19 C20 C21 -1.9(4) . . . . ? C17 C16 C21 C20 0.9(4) . . . . ? C15 C16 C21 C20 -178.6(2) . . . . ? C19 C20 C21 C16 0.2(4) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.94 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.272 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.040 data_TDZ-2 _database_code_depnum_ccdc_archive 'CCDC 923894' #TrackingRef 'TDZ-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H13 F2 N3 O2 S' _chemical_formula_sum 'C21 H13 F2 N3 O2 S' _chemical_formula_weight 409.40 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' S S 0.1246 0.1234 '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 20.5635(7) _cell_length_b 5.8117(2) _cell_length_c 32.1855(11) _cell_angle_alpha 90.00 _cell_angle_beta 106.079(2) _cell_angle_gamma 90.00 _cell_volume 3696.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.218 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9334 _exptl_absorpt_correction_T_max 0.9827 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 15007 _diffrn_reflns_av_R_equivalents 0.0316 _diffrn_reflns_av_sigmaI/netI 0.0314 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3225 _reflns_number_gt 2414 _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^)+(0.0482P)^2^+2.0705P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3225 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1063 _refine_ls_wR_factor_gt 0.0970 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL TDZ-2 in C 1 2/c 1 CELL 0.71073 20.5635 5.8117 32.1855 90.000 106.079 90.000 ZERR 8 0.0007 0.0002 0.0011 0.000 0.002 0.000 LATT 7 SYMM -X,Y, 0.50000-Z SFAC C H N O F S UNIT 168 104 24 16 16 8 MERG 2 L.S. 12 SIZE 0.32 0.10 0.08 TEMP 21 OMIT -1 50 OMIT 3 1 4 ACTA BOND $H CONF HTAB FMAP 2 PLAN 10 WGHT 0.048200 2.070500 FVAR 0.09186 S1 6 0.863163 0.441704 0.003071 11.00000 0.04681 0.04723 = 0.05404 0.00551 0.01686 0.01610 F1 5 0.657586 0.351644 0.130728 11.00000 0.06610 0.09997 = 0.08940 -0.01871 0.04538 0.00240 F2 5 1.054035 0.540045 -0.202380 11.00000 0.13904 0.13260 = 0.08036 0.01045 0.06308 -0.02092 O1 4 0.732494 -0.034917 0.142687 11.00000 0.06422 0.08255 = 0.06995 0.00598 0.02363 -0.01504 O2 4 0.906094 0.618791 -0.058204 11.00000 0.06994 0.06351 = 0.07638 0.01953 0.02924 0.03129 N1 3 0.958878 0.288105 -0.034752 11.00000 0.04328 0.04825 = 0.05080 0.00650 0.01712 0.01514 AFIX 43 H1N 2 0.989911 0.191654 -0.036164 11.00000 -1.20000 AFIX 0 N2 3 0.934378 0.075526 0.020521 11.00000 0.05201 0.05290 = 0.05855 0.01013 0.02489 0.01885 N3 3 0.891793 0.071441 0.047013 11.00000 0.05167 0.05341 = 0.06028 0.01032 0.02538 0.01930 C1 1 0.867951 -0.180007 0.260343 11.00000 0.12654 0.13260 = 0.08008 0.03922 0.01815 0.00576 AFIX 43 H1 2 0.897751 -0.213815 0.287132 11.00000 -1.20000 AFIX 0 C2 1 0.814749 -0.320709 0.242971 11.00000 0.15047 0.07710 = 0.08800 0.02687 0.05816 0.00960 AFIX 43 H2 2 0.808189 -0.451435 0.257981 11.00000 -1.20000 AFIX 0 C3 1 0.770241 -0.271861 0.203239 11.00000 0.10891 0.06246 = 0.08295 -0.00136 0.05067 -0.00779 AFIX 43 H3 2 0.733911 -0.369001 0.191350 11.00000 -1.20000 AFIX 0 C4 1 0.780390 -0.077696 0.181517 11.00000 0.07004 0.06027 = 0.05827 0.00008 0.03466 0.00370 C5 1 0.833514 0.064567 0.198531 11.00000 0.08708 0.08225 = 0.06472 0.01500 0.01242 -0.01584 AFIX 43 H5 2 0.840199 0.195690 0.183667 11.00000 -1.20000 AFIX 0 C6 1 0.877390 0.011299 0.238230 11.00000 0.11589 0.13940 = 0.07374 0.03214 -0.00185 -0.03309 AFIX 43 H6 2 0.913977 0.107463 0.250081 11.00000 -1.20000 AFIX 0 C7 1 0.744815 0.135710 0.116062 11.00000 0.04648 0.06156 = 0.05241 -0.00249 0.01376 -0.00392 C8 1 0.705250 0.330807 0.109262 11.00000 0.04247 0.07394 = 0.06047 -0.01716 0.02198 0.00107 C9 1 0.712119 0.499610 0.081474 11.00000 0.05597 0.05771 = 0.07460 -0.00721 0.02351 0.01796 AFIX 43 H9 2 0.684479 0.629074 0.077278 11.00000 -1.20000 AFIX 0 C10 1 0.760760 0.475554 0.059625 11.00000 0.05317 0.05257 = 0.05890 -0.00038 0.01960 0.01202 AFIX 43 H10 2 0.766278 0.590701 0.040824 11.00000 -1.20000 AFIX 0 C11 1 0.801517 0.281309 0.065422 11.00000 0.03754 0.04763 = 0.04505 -0.00386 0.01028 0.00690 C12 1 0.792656 0.111536 0.093760 11.00000 0.04409 0.04993 = 0.05601 0.00000 0.01376 0.00802 AFIX 43 H12 2 0.819391 -0.020092 0.097705 11.00000 -1.20000 AFIX 0 C13 1 0.852153 0.249693 0.041420 11.00000 0.03895 0.04438 = 0.04679 -0.00068 0.00902 0.00797 C14 1 0.924173 0.255171 -0.004472 11.00000 0.03896 0.04567 = 0.04524 0.00029 0.01069 0.00932 C15 1 0.945452 0.470467 -0.062809 11.00000 0.04194 0.04854 = 0.05386 0.00597 0.00839 0.00836 C16 1 0.977788 0.481815 -0.098680 11.00000 0.04397 0.05119 = 0.04740 0.00604 0.00874 0.00340 C17 1 0.964523 0.671067 -0.124590 11.00000 0.12774 0.07139 = 0.08340 0.02733 0.05005 0.03512 AFIX 43 H17 2 0.937499 0.787830 -0.118642 11.00000 -1.20000 AFIX 0 C18 1 0.990493 0.691899 -0.159376 11.00000 0.16689 0.07818 = 0.08415 0.03432 0.05898 0.01982 AFIX 43 H18 2 0.981166 0.821569 -0.176961 11.00000 -1.20000 AFIX 0 C19 1 1.029632 0.522183 -0.167699 11.00000 0.07669 0.08801 = 0.05646 0.00496 0.02748 -0.01523 C20 1 1.044582 0.336758 -0.142614 11.00000 0.08768 0.10507 = 0.06982 0.01786 0.03997 0.03467 AFIX 43 H20 2 1.072403 0.222551 -0.148550 11.00000 -1.20000 AFIX 0 C21 1 1.018330 0.315656 -0.107641 11.00000 0.08689 0.08457 = 0.06620 0.02885 0.03540 0.04076 AFIX 43 H21 2 1.028546 0.186206 -0.090046 11.00000 -1.20000 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 S1 S 0.86316(3) 0.44170(10) 0.003071(17) 0.04878(19) Uani 1 1 d . . . F1 F 0.65759(7) 0.3516(3) 0.13073(5) 0.0804(5) Uani 1 1 d . . . F2 F 1.05403(10) 0.5400(4) -0.20238(5) 0.1108(6) Uani 1 1 d . . . O1 O 0.73249(8) -0.0349(3) 0.14269(6) 0.0712(5) Uani 1 1 d . . . O2 O 0.90609(8) 0.6188(3) -0.05820(5) 0.0681(5) Uani 1 1 d . . . N1 N 0.95888(8) 0.2881(3) -0.03475(5) 0.0466(4) Uani 1 1 d . . . H1N H 0.9899 0.1917 -0.0362 0.056 Uiso 1 1 calc R . . N2 N 0.93438(9) 0.0755(3) 0.02052(6) 0.0526(5) Uani 1 1 d . . . N3 N 0.89179(9) 0.0714(3) 0.04701(6) 0.0531(5) Uani 1 1 d . . . C1 C 0.8680(2) -0.1800(8) 0.26034(11) 0.1152(12) Uani 1 1 d . . . H1 H 0.8978 -0.2138 0.2871 0.138 Uiso 1 1 calc R . . C2 C 0.8147(2) -0.3207(6) 0.24297(11) 0.1002(11) Uani 1 1 d . . . H2 H 0.8082 -0.4514 0.2580 0.120 Uiso 1 1 calc R . . C3 C 0.77024(16) -0.2719(5) 0.20324(10) 0.0800(8) Uani 1 1 d . . . H3 H 0.7339 -0.3690 0.1913 0.096 Uiso 1 1 calc R . . C4 C 0.78039(13) -0.0777(4) 0.18152(8) 0.0595(6) Uani 1 1 d . . . C5 C 0.83351(14) 0.0646(5) 0.19853(8) 0.0797(8) Uani 1 1 d . . . H5 H 0.8402 0.1957 0.1837 0.096 Uiso 1 1 calc R . . C6 C 0.87739(18) 0.0113(7) 0.23823(10) 0.1153(13) Uani 1 1 d . . . H6 H 0.9140 0.1075 0.2501 0.138 Uiso 1 1 calc R . . C7 C 0.74482(10) 0.1357(4) 0.11606(7) 0.0535(6) Uani 1 1 d . . . C8 C 0.70525(10) 0.3308(5) 0.10926(7) 0.0574(6) Uani 1 1 d . . . C9 C 0.71212(11) 0.4996(4) 0.08147(8) 0.0617(6) Uani 1 1 d . . . H9 H 0.6845 0.6291 0.0773 0.074 Uiso 1 1 calc R . . C10 C 0.76076(10) 0.4756(4) 0.05962(7) 0.0541(6) Uani 1 1 d . . . H10 H 0.7663 0.5907 0.0408 0.065 Uiso 1 1 calc R . . C11 C 0.80152(9) 0.2813(4) 0.06542(6) 0.0436(5) Uani 1 1 d . . . C12 C 0.79266(10) 0.1115(4) 0.09376(7) 0.0500(5) Uani 1 1 d . . . H12 H 0.8194 -0.0201 0.0977 0.060 Uiso 1 1 calc R . . C13 C 0.85215(9) 0.2497(4) 0.04142(6) 0.0439(5) Uani 1 1 d . . . C14 C 0.92417(9) 0.2552(4) -0.00447(6) 0.0435(5) Uani 1 1 d . . . C15 C 0.94545(10) 0.4705(4) -0.06281(7) 0.0491(5) Uani 1 1 d . . . C16 C 0.97779(10) 0.4818(4) -0.09868(7) 0.0483(5) Uani 1 1 d . . . C17 C 0.96452(16) 0.6711(5) -0.12459(9) 0.0900(9) Uani 1 1 d . . . H17 H 0.9375 0.7878 -0.1186 0.108 Uiso 1 1 calc R . . C18 C 0.99049(19) 0.6919(6) -0.15938(10) 0.1049(11) Uani 1 1 d . . . H18 H 0.9812 0.8216 -0.1770 0.126 Uiso 1 1 calc R . . C19 C 1.02963(14) 0.5222(6) -0.16770(8) 0.0719(7) Uani 1 1 d . . . C20 C 1.04458(14) 0.3368(6) -0.14261(9) 0.0839(9) Uani 1 1 d . . . H20 H 1.0724 0.2226 -0.1486 0.101 Uiso 1 1 calc R . . C21 C 1.01833(13) 0.3157(5) -0.10764(8) 0.0764(8) Uani 1 1 d . . . H21 H 1.0285 0.1862 -0.0900 0.092 Uiso 1 1 calc R . . 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 S1 0.0468(3) 0.0472(3) 0.0540(3) 0.0055(3) 0.0169(2) 0.0161(2) F1 0.0661(9) 0.1000(12) 0.0894(10) -0.0187(9) 0.0454(8) 0.0024(8) F2 0.1390(15) 0.1326(17) 0.0804(11) 0.0105(11) 0.0631(11) -0.0209(12) O1 0.0642(10) 0.0826(13) 0.0699(11) 0.0060(10) 0.0236(9) -0.0150(9) O2 0.0699(10) 0.0635(11) 0.0764(11) 0.0195(9) 0.0292(9) 0.0313(9) N1 0.0433(9) 0.0483(11) 0.0508(10) 0.0065(9) 0.0171(8) 0.0151(8) N2 0.0520(10) 0.0529(12) 0.0586(11) 0.0101(10) 0.0249(9) 0.0188(9) N3 0.0517(10) 0.0534(12) 0.0603(11) 0.0103(9) 0.0254(9) 0.0193(9) C1 0.127(3) 0.133(4) 0.080(2) 0.039(2) 0.018(2) 0.006(3) C2 0.150(3) 0.077(2) 0.088(2) 0.0269(19) 0.058(2) 0.010(2) C3 0.109(2) 0.0625(18) 0.083(2) -0.0014(16) 0.0507(18) -0.0078(16) C4 0.0700(16) 0.0603(16) 0.0583(15) 0.0001(13) 0.0347(13) 0.0037(13) C5 0.0871(19) 0.082(2) 0.0647(17) 0.0150(15) 0.0124(15) -0.0158(16) C6 0.116(3) 0.139(3) 0.074(2) 0.032(2) -0.0018(19) -0.033(2) C7 0.0465(13) 0.0616(15) 0.0524(13) -0.0025(12) 0.0138(11) -0.0039(11) C8 0.0425(12) 0.0739(18) 0.0605(14) -0.0172(13) 0.0220(11) 0.0011(12) C9 0.0560(14) 0.0577(16) 0.0746(16) -0.0072(13) 0.0235(12) 0.0180(11) C10 0.0532(13) 0.0526(14) 0.0589(13) -0.0004(11) 0.0196(11) 0.0120(11) C11 0.0375(11) 0.0476(13) 0.0450(11) -0.0039(10) 0.0103(9) 0.0069(9) C12 0.0441(12) 0.0499(14) 0.0560(13) 0.0000(11) 0.0138(10) 0.0080(10) C13 0.0389(11) 0.0444(12) 0.0468(12) -0.0007(10) 0.0090(9) 0.0080(9) C14 0.0390(11) 0.0457(13) 0.0452(12) 0.0003(10) 0.0107(9) 0.0093(9) C15 0.0419(11) 0.0485(13) 0.0539(13) 0.0060(11) 0.0084(10) 0.0084(10) C16 0.0440(12) 0.0512(14) 0.0474(12) 0.0060(10) 0.0087(10) 0.0034(10) C17 0.128(3) 0.071(2) 0.0834(19) 0.0273(17) 0.0500(19) 0.0351(18) C18 0.167(3) 0.078(2) 0.084(2) 0.0343(18) 0.059(2) 0.020(2) C19 0.0767(17) 0.088(2) 0.0565(15) 0.0050(15) 0.0275(13) -0.0152(16) C20 0.0877(19) 0.105(2) 0.0698(17) 0.0179(17) 0.0400(15) 0.0347(17) C21 0.0869(18) 0.085(2) 0.0662(16) 0.0288(15) 0.0354(14) 0.0408(16) _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 S1 C13 1.725(2) . ? S1 C14 1.7254(19) . ? F1 C8 1.352(2) . ? F2 C19 1.349(3) . ? O1 C7 1.379(3) . ? O1 C4 1.383(3) . ? O2 C15 1.219(2) . ? N1 C15 1.370(3) . ? N1 C14 1.371(2) . ? N1 H1N 0.8600 . ? N2 C14 1.299(3) . ? N2 N3 1.381(2) . ? N3 C13 1.300(3) . ? C1 C2 1.356(5) . ? C1 C6 1.363(5) . ? C1 H1 0.9300 . ? C2 C3 1.380(4) . ? C2 H2 0.9300 . ? C3 C4 1.373(3) . ? C3 H3 0.9300 . ? C4 C5 1.358(4) . ? C5 C6 1.380(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.376(3) . ? C7 C8 1.377(3) . ? C8 C9 1.361(3) . ? C9 C10 1.380(3) . ? C9 H9 0.9300 . ? C10 C11 1.387(3) . ? C10 H10 0.9300 . ? C11 C12 1.389(3) . ? C11 C13 1.470(3) . ? C12 H12 0.9300 . ? C15 C16 1.485(3) . ? C16 C21 1.358(3) . ? C16 C17 1.361(3) . ? C17 C18 1.373(4) . ? C17 H17 0.9300 . ? C18 C19 1.346(4) . ? C18 H18 0.9300 . ? C19 C20 1.330(4) . ? C20 C21 1.382(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? 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 C13 S1 C14 86.50(10) . . ? C7 O1 C4 118.91(17) . . ? C15 N1 C14 121.79(17) . . ? C15 N1 H1N 119.1 . . ? C14 N1 H1N 119.1 . . ? C14 N2 N3 112.01(16) . . ? C13 N3 N2 112.42(17) . . ? C2 C1 C6 119.5(3) . . ? C2 C1 H1 120.3 . . ? C6 C1 H1 120.3 . . ? C1 C2 C3 120.7(3) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 120.9(3) . . ? C5 C4 O1 123.2(2) . . ? C3 C4 O1 115.9(2) . . ? C4 C5 C6 118.9(3) . . ? C4 C5 H5 120.5 . . ? C6 C5 H5 120.5 . . ? C1 C6 C5 121.0(3) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C12 C7 C8 118.5(2) . . ? C12 C7 O1 122.1(2) . . ? C8 C7 O1 119.2(2) . . ? F1 C8 C9 119.5(2) . . ? F1 C8 C7 118.2(2) . . ? C9 C8 C7 122.2(2) . . ? C8 C9 C10 118.9(2) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C9 C10 C11 120.7(2) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C10 C11 C12 118.81(19) . . ? C10 C11 C13 121.4(2) . . ? C12 C11 C13 119.80(18) . . ? C7 C12 C11 120.8(2) . . ? C7 C12 H12 119.6 . . ? C11 C12 H12 119.6 . . ? N3 C13 C11 122.37(19) . . ? N3 C13 S1 114.41(15) . . ? C11 C13 S1 123.21(15) . . ? N2 C14 N1 121.71(17) . . ? N2 C14 S1 114.64(15) . . ? N1 C14 S1 123.65(15) . . ? O2 C15 N1 119.09(19) . . ? O2 C15 C16 121.2(2) . . ? N1 C15 C16 119.67(18) . . ? C21 C16 C17 118.4(2) . . ? C21 C16 C15 124.5(2) . . ? C17 C16 C15 117.1(2) . . ? C16 C17 C18 120.9(3) . . ? C16 C17 H17 119.5 . . ? C18 C17 H17 119.5 . . ? C19 C18 C17 119.1(3) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C20 C19 C18 121.5(3) . . ? C20 C19 F2 119.2(3) . . ? C18 C19 F2 119.2(3) . . ? C19 C20 C21 119.3(3) . . ? C19 C20 H20 120.3 . . ? C21 C20 H20 120.3 . . ? C16 C21 C20 120.7(2) . . ? C16 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? 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 C14 N2 N3 C13 -1.1(3) . . . . ? C6 C1 C2 C3 0.0(6) . . . . ? C1 C2 C3 C4 -0.3(5) . . . . ? C2 C3 C4 C5 0.3(4) . . . . ? C2 C3 C4 O1 -177.7(2) . . . . ? C7 O1 C4 C5 11.9(3) . . . . ? C7 O1 C4 C3 -170.1(2) . . . . ? C3 C4 C5 C6 -0.1(4) . . . . ? O1 C4 C5 C6 177.8(3) . . . . ? C2 C1 C6 C5 0.3(6) . . . . ? C4 C5 C6 C1 -0.2(6) . . . . ? C4 O1 C7 C12 71.4(3) . . . . ? C4 O1 C7 C8 -112.9(2) . . . . ? C12 C7 C8 F1 178.91(19) . . . . ? O1 C7 C8 F1 3.0(3) . . . . ? C12 C7 C8 C9 -0.2(3) . . . . ? O1 C7 C8 C9 -176.1(2) . . . . ? F1 C8 C9 C10 -179.69(19) . . . . ? C7 C8 C9 C10 -0.6(4) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C9 C10 C11 C13 178.1(2) . . . . ? C8 C7 C12 C11 0.8(3) . . . . ? O1 C7 C12 C11 176.60(19) . . . . ? C10 C11 C12 C7 -0.6(3) . . . . ? C13 C11 C12 C7 -178.96(18) . . . . ? N2 N3 C13 C11 178.86(18) . . . . ? N2 N3 C13 S1 -0.1(2) . . . . ? C10 C11 C13 N3 178.5(2) . . . . ? C12 C11 C13 N3 -3.1(3) . . . . ? C10 C11 C13 S1 -2.5(3) . . . . ? C12 C11 C13 S1 175.77(16) . . . . ? C14 S1 C13 N3 0.95(17) . . . . ? C14 S1 C13 C11 -178.04(18) . . . . ? N3 N2 C14 N1 -177.02(18) . . . . ? N3 N2 C14 S1 1.9(2) . . . . ? C15 N1 C14 N2 176.18(19) . . . . ? C15 N1 C14 S1 -2.6(3) . . . . ? C13 S1 C14 N2 -1.60(17) . . . . ? C13 S1 C14 N1 177.25(18) . . . . ? C14 N1 C15 O2 6.9(3) . . . . ? C14 N1 C15 C16 -171.90(18) . . . . ? O2 C15 C16 C21 -175.2(2) . . . . ? N1 C15 C16 C21 3.5(3) . . . . ? O2 C15 C16 C17 3.6(3) . . . . ? N1 C15 C16 C17 -177.7(2) . . . . ? C21 C16 C17 C18 1.1(4) . . . . ? C15 C16 C17 C18 -177.8(3) . . . . ? C16 C17 C18 C19 -0.1(5) . . . . ? C17 C18 C19 C20 -1.1(5) . . . . ? C17 C18 C19 F2 178.6(3) . . . . ? C18 C19 C20 C21 1.2(5) . . . . ? F2 C19 C20 C21 -178.5(3) . . . . ? C17 C16 C21 C20 -1.0(4) . . . . ? C15 C16 C21 C20 177.8(2) . . . . ? C19 C20 C21 C16 -0.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.155 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.035 data_TDZ-3 _database_code_depnum_ccdc_archive 'CCDC 923895' #TrackingRef 'TDZ-3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 F N3 O2 S' _chemical_formula_sum 'C22 H16 F N3 O2 S' _chemical_formula_weight 405.44 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' S S 0.1246 0.1234 '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 8.2327(16) _cell_length_b 8.8616(17) _cell_length_c 13.577(3) _cell_angle_alpha 87.741(12) _cell_angle_beta 85.797(10) _cell_angle_gamma 73.758(10) _cell_volume 948.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.420 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.205 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9506 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(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 19522 _diffrn_reflns_av_R_equivalents 0.0253 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 30.60 _reflns_number_total 5738 _reflns_number_gt 3433 _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^)+(0.0621P)^2^+0.1219P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5738 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1412 _refine_ls_wR_factor_gt 0.1181 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _iucr_refine_instruction_details ; TITL TDZ-3 in P-1 CELL 0.71073 8.2327 8.8616 13.5773 87.741 85.797 73.758 ZERR 2.00 0.0016 0.0017 0.0027 0.012 0.010 0.010 LATT 1 SFAC C H N O F S UNIT 44 32 6 4 2 2 MERG 2 L.S. 10 SIZE 0.25 0.18 0.05 TEMP 21 ACTA HTAB BOND $H CONF FMAP 2 PLAN 10 WGHT 0.062100 0.121900 FVAR 0.14901 S1 6 0.765049 0.297605 0.488711 11.00000 0.05095 0.04267 = 0.05603 0.01040 -0.01596 -0.02014 F1 5 1.459103 0.170024 0.744296 11.00000 0.06156 0.10478 = 0.07655 -0.00019 -0.03332 -0.02429 O1 4 0.554411 0.432616 0.355169 11.00000 0.06853 0.05936 = 0.08508 0.02493 -0.02867 -0.03464 O2 4 1.326297 -0.080022 0.781857 11.00000 0.08743 0.05345 = 0.05923 0.00193 -0.02768 0.00835 N1 3 0.489780 0.221161 0.425067 11.00000 0.04528 0.04750 = 0.04981 0.00994 -0.01170 -0.02098 AFIX 43 H1N 2 0.422592 0.161999 0.428301 11.00000 -1.20000 AFIX 0 N2 3 0.657137 0.059410 0.540291 11.00000 0.04897 0.05223 = 0.05555 0.01366 -0.01486 -0.02283 N3 3 0.797921 0.046242 0.592068 11.00000 0.05007 0.05013 = 0.05693 0.01293 -0.01567 -0.02184 C1 1 1.284371 -0.062331 1.086002 11.00000 0.07964 0.13311 = 0.06077 0.02382 -0.01461 -0.03184 AFIX 43 H1 2 1.276869 -0.060818 1.154654 11.00000 -1.20000 AFIX 0 C2 1 1.394591 -0.181983 1.037589 11.00000 0.08510 0.10313 = 0.07509 0.03910 -0.02849 -0.01817 AFIX 43 H2 2 1.463418 -0.263370 1.073630 11.00000 -1.20000 AFIX 0 C3 1 1.408020 -0.186991 0.936612 11.00000 0.07455 0.07156 = 0.07577 0.01737 -0.02192 -0.00350 AFIX 43 H3 2 1.484672 -0.270922 0.904436 11.00000 -1.20000 AFIX 0 C4 1 1.307089 -0.066775 0.883588 11.00000 0.05469 0.05537 = 0.05737 0.01155 -0.02149 -0.01822 C5 1 1.194025 0.054973 0.931275 11.00000 0.07995 0.06898 = 0.06254 0.00919 -0.01498 -0.00500 AFIX 43 H5 2 1.124288 0.136270 0.895616 11.00000 -1.20000 AFIX 0 C6 1 1.184206 0.056244 1.033004 11.00000 0.09925 0.10332 = 0.06283 0.00264 -0.00492 -0.00773 AFIX 43 H6 2 1.107826 0.139568 1.065873 11.00000 -1.20000 AFIX 0 C7 1 1.244433 0.047130 0.724874 11.00000 0.05994 0.04637 = 0.04715 0.00115 -0.01685 -0.00355 C8 1 1.315665 0.169628 0.702471 11.00000 0.04719 0.06533 = 0.04991 -0.00567 -0.01571 -0.01395 C9 1 1.243448 0.290234 0.640331 11.00000 0.05378 0.05809 = 0.05433 0.00243 -0.01118 -0.02441 AFIX 43 H9 2 1.292444 0.372024 0.626529 11.00000 -1.20000 AFIX 0 C10 1 1.096259 0.288985 0.598184 11.00000 0.05199 0.04565 = 0.04694 0.00633 -0.01255 -0.01763 AFIX 43 H10 2 1.046527 0.370248 0.555128 11.00000 -1.20000 AFIX 0 C11 1 1.021284 0.167856 0.619219 11.00000 0.04445 0.03843 = 0.04486 -0.00089 -0.00718 -0.01152 C12 1 1.097150 0.047505 0.683279 11.00000 0.06056 0.03995 = 0.05126 0.00404 -0.01075 -0.01433 AFIX 43 H12 2 1.047925 -0.033828 0.698281 11.00000 -1.20000 AFIX 0 C13 1 0.867135 0.160710 0.573614 11.00000 0.04354 0.04159 = 0.04514 0.00356 -0.00759 -0.01372 C14 1 0.625014 0.184815 0.483640 11.00000 0.04239 0.04435 = 0.04355 0.00298 -0.00373 -0.01574 C15 1 0.458224 0.349249 0.361318 11.00000 0.05115 0.04215 = 0.05036 0.00633 -0.00790 -0.01735 C16 1 0.306049 0.381690 0.303362 11.00000 0.05154 0.04006 = 0.04563 0.00599 -0.00940 -0.01343 C17 1 0.283797 0.503622 0.234152 11.00000 0.05753 0.05019 = 0.06604 0.01722 -0.01111 -0.02241 AFIX 43 H17 2 0.362223 0.561709 0.226117 11.00000 -1.20000 AFIX 0 C18 1 0.146199 0.538960 0.177361 11.00000 0.06436 0.05340 = 0.06004 0.01994 -0.01462 -0.01464 AFIX 43 H18 2 0.134506 0.620109 0.130528 11.00000 -1.20000 AFIX 0 C19 1 0.024515 0.458051 0.187427 11.00000 0.05631 0.04535 = 0.05195 0.00273 -0.01310 -0.01129 C20 1 0.045459 0.340105 0.258349 11.00000 0.06773 0.05662 = 0.07598 0.01942 -0.02772 -0.03110 AFIX 43 H20 2 -0.035675 0.285151 0.268186 11.00000 -1.20000 AFIX 0 C21 1 0.183309 0.301638 0.314931 11.00000 0.06803 0.05162 = 0.06760 0.02458 -0.02503 -0.02825 AFIX 43 H21 2 0.194435 0.220542 0.361767 11.00000 -1.20000 AFIX 0 C22 1 -0.128796 0.495320 0.127007 11.00000 0.07070 0.06867 = 0.07136 0.00993 -0.02775 -0.01402 AFIX 137 H22A 2 -0.120779 0.409366 0.084314 11.00000 -1.50000 H22B 2 -0.133803 0.588993 0.087929 11.00000 -1.50000 H22C 2 -0.229443 0.511335 0.170299 11.00000 -1.50000 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 S1 S 0.76505(6) 0.29761(5) 0.48871(3) 0.04811(15) Uani 1 1 d . . . F1 F 1.45910(16) 0.17002(16) 0.74430(9) 0.0793(4) Uani 1 1 d . . . O1 O 0.55441(18) 0.43262(15) 0.35517(11) 0.0671(4) Uani 1 1 d . . . O2 O 1.3263(2) -0.08002(15) 0.78186(10) 0.0713(4) Uani 1 1 d . . . N1 N 0.48978(18) 0.22116(16) 0.42507(10) 0.0457(3) Uani 1 1 d . . . H1N H 0.4226 0.1620 0.4283 0.055 Uiso 1 1 calc R . . N2 N 0.65714(19) 0.05941(17) 0.54029(11) 0.0503(4) Uani 1 1 d . . . N3 N 0.79792(19) 0.04624(17) 0.59207(11) 0.0505(4) Uani 1 1 d . . . C1 C 1.2844(4) -0.0623(4) 1.08600(18) 0.0909(8) Uani 1 1 d . . . H1 H 1.2769 -0.0608 1.1547 0.109 Uiso 1 1 calc R . . C2 C 1.3946(4) -0.1820(3) 1.03759(18) 0.0893(8) Uani 1 1 d . . . H2 H 1.4634 -0.2634 1.0736 0.107 Uiso 1 1 calc R . . C3 C 1.4080(3) -0.1870(3) 0.93661(17) 0.0770(7) Uani 1 1 d . . . H3 H 1.4847 -0.2709 0.9044 0.092 Uiso 1 1 calc R . . C4 C 1.3071(2) -0.0668(2) 0.88359(14) 0.0546(5) Uani 1 1 d . . . C5 C 1.1940(3) 0.0550(3) 0.93128(16) 0.0734(6) Uani 1 1 d . . . H5 H 1.1243 0.1363 0.8956 0.088 Uiso 1 1 calc R . . C6 C 1.1842(4) 0.0562(3) 1.03300(18) 0.0927(8) Uani 1 1 d . . . H6 H 1.1078 0.1396 1.0659 0.111 Uiso 1 1 calc R . . C7 C 1.2444(3) 0.0471(2) 0.72487(13) 0.0528(5) Uani 1 1 d . . . C8 C 1.3157(2) 0.1696(2) 0.70247(13) 0.0537(4) Uani 1 1 d . . . C9 C 1.2434(2) 0.2902(2) 0.64033(13) 0.0533(4) Uani 1 1 d . . . H9 H 1.2924 0.3720 0.6265 0.064 Uiso 1 1 calc R . . C10 C 1.0963(2) 0.2890(2) 0.59818(12) 0.0471(4) Uani 1 1 d . . . H10 H 1.0465 0.3702 0.5551 0.057 Uiso 1 1 calc R . . C11 C 1.0213(2) 0.16786(18) 0.61922(12) 0.0424(4) Uani 1 1 d . . . C12 C 1.0972(2) 0.0475(2) 0.68328(13) 0.0503(4) Uani 1 1 d . . . H12 H 1.0479 -0.0338 0.6983 0.060 Uiso 1 1 calc R . . C13 C 0.8671(2) 0.16071(18) 0.57361(12) 0.0429(4) Uani 1 1 d . . . C14 C 0.6250(2) 0.18481(19) 0.48364(12) 0.0427(4) Uani 1 1 d . . . C15 C 0.4582(2) 0.3492(2) 0.36132(12) 0.0470(4) Uani 1 1 d . . . C16 C 0.3060(2) 0.38169(19) 0.30336(12) 0.0455(4) Uani 1 1 d . . . C17 C 0.2838(3) 0.5036(2) 0.23415(14) 0.0566(5) Uani 1 1 d . . . H17 H 0.3622 0.5617 0.2261 0.068 Uiso 1 1 calc R . . C18 C 0.1462(3) 0.5390(2) 0.17736(14) 0.0596(5) Uani 1 1 d . . . H18 H 0.1345 0.6201 0.1305 0.072 Uiso 1 1 calc R . . C19 C 0.0245(2) 0.4581(2) 0.18743(13) 0.0514(4) Uani 1 1 d . . . C20 C 0.0455(3) 0.3401(2) 0.25835(15) 0.0634(5) Uani 1 1 d . . . H20 H -0.0357 0.2852 0.2682 0.076 Uiso 1 1 calc R . . C21 C 0.1833(3) 0.3016(2) 0.31493(15) 0.0597(5) Uani 1 1 d . . . H21 H 0.1944 0.2205 0.3618 0.072 Uiso 1 1 calc R . . C22 C -0.1288(3) 0.4953(3) 0.12701(16) 0.0705(6) Uani 1 1 d . . . H22A H -0.1208 0.4094 0.0843 0.106 Uiso 1 1 calc R . . H22B H -0.1338 0.5890 0.0879 0.106 Uiso 1 1 calc R . . H22C H -0.2294 0.5113 0.1703 0.106 Uiso 1 1 calc R . . 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 S1 0.0509(3) 0.0427(2) 0.0560(3) 0.01040(18) -0.0160(2) -0.02014(19) F1 0.0616(8) 0.1048(10) 0.0766(8) -0.0002(7) -0.0333(6) -0.0243(7) O1 0.0685(9) 0.0594(8) 0.0851(10) 0.0249(7) -0.0287(7) -0.0346(7) O2 0.0874(11) 0.0535(8) 0.0592(8) 0.0019(6) -0.0277(7) 0.0084(7) N1 0.0453(8) 0.0475(8) 0.0498(8) 0.0099(6) -0.0117(6) -0.0210(6) N2 0.0490(9) 0.0522(8) 0.0556(8) 0.0137(7) -0.0149(7) -0.0228(7) N3 0.0501(9) 0.0501(8) 0.0569(9) 0.0129(6) -0.0157(7) -0.0218(7) C1 0.0796(18) 0.133(2) 0.0608(14) 0.0238(15) -0.0146(13) -0.0318(17) C2 0.0851(18) 0.1031(19) 0.0751(16) 0.0391(14) -0.0285(14) -0.0182(15) C3 0.0746(15) 0.0716(14) 0.0758(15) 0.0174(11) -0.0219(12) -0.0035(12) C4 0.0547(11) 0.0554(11) 0.0574(11) 0.0115(8) -0.0215(9) -0.0182(9) C5 0.0799(16) 0.0690(13) 0.0625(13) 0.0092(10) -0.0150(11) -0.0050(12) C6 0.099(2) 0.1033(19) 0.0628(14) 0.0026(13) -0.0049(13) -0.0077(16) C7 0.0599(12) 0.0464(10) 0.0472(9) 0.0011(7) -0.0169(8) -0.0035(8) C8 0.0472(10) 0.0653(12) 0.0499(10) -0.0057(8) -0.0157(8) -0.0140(9) C9 0.0538(11) 0.0581(11) 0.0543(10) 0.0024(8) -0.0112(8) -0.0244(9) C10 0.0520(10) 0.0457(9) 0.0469(9) 0.0063(7) -0.0125(8) -0.0176(8) C11 0.0444(9) 0.0384(8) 0.0449(9) -0.0009(7) -0.0072(7) -0.0115(7) C12 0.0606(11) 0.0399(9) 0.0513(10) 0.0040(7) -0.0107(8) -0.0143(8) C13 0.0435(9) 0.0416(9) 0.0451(9) 0.0036(7) -0.0076(7) -0.0137(7) C14 0.0424(9) 0.0443(9) 0.0435(8) 0.0030(7) -0.0037(7) -0.0157(7) C15 0.0512(10) 0.0421(9) 0.0504(9) 0.0063(7) -0.0079(8) -0.0173(8) C16 0.0515(10) 0.0401(8) 0.0456(9) 0.0060(7) -0.0094(8) -0.0134(7) C17 0.0575(11) 0.0502(10) 0.0660(12) 0.0172(9) -0.0111(9) -0.0224(9) C18 0.0644(13) 0.0534(11) 0.0600(11) 0.0199(9) -0.0146(10) -0.0146(9) C19 0.0563(11) 0.0454(9) 0.0519(10) 0.0027(8) -0.0131(8) -0.0113(8) C20 0.0677(13) 0.0566(11) 0.0760(13) 0.0194(9) -0.0277(11) -0.0311(10) C21 0.0680(13) 0.0516(10) 0.0676(12) 0.0246(9) -0.0250(10) -0.0282(9) C22 0.0707(14) 0.0687(13) 0.0714(13) 0.0099(10) -0.0278(11) -0.0140(11) _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 S1 C13 1.7229(16) . ? S1 C14 1.7305(17) . ? F1 C8 1.348(2) . ? O1 C15 1.222(2) . ? O2 C7 1.380(2) . ? O2 C4 1.385(2) . ? N1 C14 1.373(2) . ? N1 C15 1.377(2) . ? N1 H1N 0.8600 . ? N2 C14 1.302(2) . ? N2 N3 1.374(2) . ? N3 C13 1.303(2) . ? C1 C2 1.345(4) . ? C1 C6 1.358(3) . ? C1 H1 0.9300 . ? C2 C3 1.369(3) . ? C2 H2 0.9300 . ? C3 C4 1.370(3) . ? C3 H3 0.9300 . ? C4 C5 1.362(3) . ? C5 C6 1.378(3) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.374(3) . ? C7 C8 1.385(3) . ? C8 C9 1.362(3) . ? C9 C10 1.380(2) . ? C9 H9 0.9300 . ? C10 C11 1.391(2) . ? C10 H10 0.9300 . ? C11 C12 1.385(2) . ? C11 C13 1.470(2) . ? C12 H12 0.9300 . ? C15 C16 1.482(2) . ? C16 C21 1.385(3) . ? C16 C17 1.385(2) . ? C17 C18 1.373(3) . ? C17 H17 0.9300 . ? C18 C19 1.382(3) . ? C18 H18 0.9300 . ? C19 C20 1.376(2) . ? C19 C22 1.507(3) . ? C20 C21 1.373(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C13 S1 C14 86.60(8) . . ? C7 O2 C4 118.20(14) . . ? C14 N1 C15 122.14(14) . . ? C14 N1 H1N 118.9 . . ? C15 N1 H1N 118.9 . . ? C14 N2 N3 111.40(14) . . ? C13 N3 N2 113.48(13) . . ? C2 C1 C6 118.9(2) . . ? C2 C1 H1 120.5 . . ? C6 C1 H1 120.5 . . ? C1 C2 C3 121.7(2) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C2 C3 C4 119.1(2) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C4 C3 120.08(19) . . ? C5 C4 O2 123.84(16) . . ? C3 C4 O2 116.07(18) . . ? C4 C5 C6 119.2(2) . . ? C4 C5 H5 120.4 . . ? C6 C5 H5 120.4 . . ? C1 C6 C5 121.0(2) . . ? C1 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C12 C7 O2 119.95(18) . . ? C12 C7 C8 119.08(16) . . ? O2 C7 C8 120.78(18) . . ? F1 C8 C9 119.32(18) . . ? F1 C8 C7 118.99(17) . . ? C9 C8 C7 121.69(17) . . ? C8 C9 C10 118.85(17) . . ? C8 C9 H9 120.6 . . ? C10 C9 H9 120.6 . . ? C9 C10 C11 120.92(16) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C12 C11 C10 118.84(16) . . ? C12 C11 C13 118.82(15) . . ? C10 C11 C13 122.32(15) . . ? C7 C12 C11 120.62(17) . . ? C7 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? N3 C13 C11 122.48(14) . . ? N3 C13 S1 113.76(13) . . ? C11 C13 S1 123.73(12) . . ? N2 C14 N1 121.27(15) . . ? N2 C14 S1 114.77(13) . . ? N1 C14 S1 123.96(12) . . ? O1 C15 N1 119.38(16) . . ? O1 C15 C16 122.43(15) . . ? N1 C15 C16 118.18(15) . . ? C21 C16 C17 117.90(16) . . ? C21 C16 C15 124.87(15) . . ? C17 C16 C15 117.22(16) . . ? C18 C17 C16 120.17(18) . . ? C18 C17 H17 119.9 . . ? C16 C17 H17 119.9 . . ? C17 C18 C19 122.25(17) . . ? C17 C18 H18 118.9 . . ? C19 C18 H18 118.9 . . ? C20 C19 C18 117.04(17) . . ? C20 C19 C22 119.48(18) . . ? C18 C19 C22 123.46(17) . . ? C21 C20 C19 121.56(18) . . ? C21 C20 H20 119.2 . . ? C19 C20 H20 119.2 . . ? C20 C21 C16 121.04(17) . . ? C20 C21 H21 119.5 . . ? C16 C21 H21 119.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C14 N2 N3 C13 0.2(2) . . . . ? C6 C1 C2 C3 0.0(5) . . . . ? C1 C2 C3 C4 0.3(4) . . . . ? C2 C3 C4 C5 -0.6(4) . . . . ? C2 C3 C4 O2 -179.5(2) . . . . ? C7 O2 C4 C5 9.6(3) . . . . ? C7 O2 C4 C3 -171.6(2) . . . . ? C3 C4 C5 C6 0.7(4) . . . . ? O2 C4 C5 C6 179.5(2) . . . . ? C2 C1 C6 C5 0.2(5) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C4 O2 C7 C12 -101.8(2) . . . . ? C4 O2 C7 C8 83.3(2) . . . . ? C12 C7 C8 F1 179.21(16) . . . . ? O2 C7 C8 F1 -5.8(3) . . . . ? C12 C7 C8 C9 0.0(3) . . . . ? O2 C7 C8 C9 174.95(16) . . . . ? F1 C8 C9 C10 -179.76(16) . . . . ? C7 C8 C9 C10 -0.6(3) . . . . ? C8 C9 C10 C11 0.6(3) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C9 C10 C11 C13 -178.34(16) . . . . ? O2 C7 C12 C11 -174.50(16) . . . . ? C8 C7 C12 C11 0.5(3) . . . . ? C10 C11 C12 C7 -0.4(3) . . . . ? C13 C11 C12 C7 177.84(16) . . . . ? N2 N3 C13 C11 -178.52(15) . . . . ? N2 N3 C13 S1 -0.4(2) . . . . ? C12 C11 C13 N3 0.8(3) . . . . ? C10 C11 C13 N3 179.00(16) . . . . ? C12 C11 C13 S1 -177.11(13) . . . . ? C10 C11 C13 S1 1.1(2) . . . . ? C14 S1 C13 N3 0.38(13) . . . . ? C14 S1 C13 C11 178.47(15) . . . . ? N3 N2 C14 N1 179.93(15) . . . . ? N3 N2 C14 S1 0.11(19) . . . . ? C15 N1 C14 N2 -176.96(15) . . . . ? C15 N1 C14 S1 2.8(2) . . . . ? C13 S1 C14 N2 -0.27(13) . . . . ? C13 S1 C14 N1 179.92(16) . . . . ? C14 N1 C15 O1 1.1(3) . . . . ? C14 N1 C15 C16 -178.14(15) . . . . ? O1 C15 C16 C21 -172.78(19) . . . . ? N1 C15 C16 C21 6.4(3) . . . . ? O1 C15 C16 C17 5.7(3) . . . . ? N1 C15 C16 C17 -175.11(15) . . . . ? C21 C16 C17 C18 -2.0(3) . . . . ? C15 C16 C17 C18 179.43(17) . . . . ? C16 C17 C18 C19 1.1(3) . . . . ? C17 C18 C19 C20 0.8(3) . . . . ? C17 C18 C19 C22 179.28(19) . . . . ? C18 C19 C20 C21 -1.6(3) . . . . ? C22 C19 C20 C21 179.78(19) . . . . ? C19 C20 C21 C16 0.7(3) . . . . ? C17 C16 C21 C20 1.1(3) . . . . ? C15 C16 C21 C20 179.60(18) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 30.60 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.219 _refine_diff_density_min -0.306 _refine_diff_density_rms 0.043 data_TDZ-4 _database_code_depnum_ccdc_archive 'CCDC 923896' #TrackingRef 'TDZ-4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H16 F N3 O3 S' _chemical_formula_sum 'C22 H16 F N3 O3 S' _chemical_formula_weight 421.44 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' S S 0.1246 0.1234 '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 8.4625(4) _cell_length_b 8.7356(4) _cell_length_c 13.4092(6) _cell_angle_alpha 86.664(3) _cell_angle_beta 82.318(3) _cell_angle_gamma 74.281(3) _cell_volume 945.39(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.480 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.212 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.9548 _exptl_absorpt_correction_T_max 0.9628 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 15295 _diffrn_reflns_av_R_equivalents 0.0532 _diffrn_reflns_av_sigmaI/netI 0.0632 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3310 _reflns_number_gt 2090 _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^)+(0.0473P)^2^+0.0747P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3310 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0951 _refine_ls_R_factor_gt 0.0488 _refine_ls_wR_factor_ref 0.1104 _refine_ls_wR_factor_gt 0.0961 _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_instruction_details ; TITL TDZ-4 in P -1 CELL 0.71073 8.4625 8.7356 13.4092 86.664 82.318 74.281 ZERR 2.00 0.0004 0.0004 0.0006 0.003 0.003 0.003 LATT 1 SFAC C H N O F S UNIT 44 32 6 6 2 2 MERG 2 FMAP 2 PLAN 5 OMIT -1 1 3 OMIT -1 50 ACTA HTAB CONF BOND $H SIZE 0.22 0.20 0.18 TEMP 23 L.S. 10 WGHT 0.047300 0.074700 FVAR 0.27874 C1 1 -0.307682 0.540026 -0.092435 11.00000 0.06583 0.09674 = 0.04402 0.00859 -0.01181 -0.03101 AFIX 43 H1 2 -0.313996 0.530279 -0.160388 11.00000 -1.20000 AFIX 0 C2 1 -0.407603 0.665461 -0.040443 11.00000 0.06549 0.07457 = 0.05619 0.03177 -0.02840 -0.02786 AFIX 43 H2 2 -0.483548 0.742213 -0.073329 11.00000 -1.20000 AFIX 0 C3 1 -0.399326 0.681955 0.059987 11.00000 0.05450 0.04408 = 0.06274 0.01251 -0.01907 -0.00985 AFIX 43 H3 2 -0.468347 0.769116 0.094678 11.00000 -1.20000 AFIX 0 C4 1 -0.287676 0.567829 0.108163 11.00000 0.04658 0.04406 = 0.04409 0.00731 -0.01994 -0.01819 C5 1 -0.185717 0.439701 0.057904 11.00000 0.06099 0.06025 = 0.05387 0.00154 -0.01865 -0.00136 AFIX 43 H5 2 -0.110347 0.362238 0.090723 11.00000 -1.20000 AFIX 0 C6 1 -0.197298 0.428004 -0.042866 11.00000 0.07223 0.09459 = 0.05379 -0.01609 -0.00956 -0.00310 AFIX 43 H6 2 -0.128054 0.341469 -0.078043 11.00000 -1.20000 AFIX 0 C7 1 -0.212410 0.464860 0.269203 11.00000 0.05054 0.03766 = 0.03964 0.00012 -0.01609 -0.00667 C8 1 -0.286504 0.342806 0.294161 11.00000 0.04077 0.05636 = 0.04357 -0.00579 -0.01359 -0.01407 C9 1 -0.224182 0.222331 0.358994 11.00000 0.05089 0.04695 = 0.04878 -0.00109 -0.01079 -0.02487 AFIX 43 H9 2 -0.274551 0.140098 0.374196 11.00000 -1.20000 AFIX 0 C10 1 -0.084869 0.224216 0.401848 11.00000 0.04767 0.03884 = 0.04016 0.00353 -0.01225 -0.01340 AFIX 43 H10 2 -0.042407 0.143165 0.446846 11.00000 -1.20000 AFIX 0 C11 1 -0.007969 0.344592 0.378813 11.00000 0.03930 0.03346 = 0.03606 -0.00174 -0.00934 -0.01142 C12 1 -0.072823 0.464222 0.311810 11.00000 0.05015 0.03640 = 0.04205 -0.00091 -0.01197 -0.01646 AFIX 43 H12 2 -0.021450 0.545459 0.295262 11.00000 -1.20000 AFIX 0 C13 1 0.138976 0.349513 0.424070 11.00000 0.03842 0.03316 = 0.03665 -0.00015 -0.00596 -0.01087 C14 1 0.368831 0.318217 0.513418 11.00000 0.03714 0.03388 = 0.03647 0.00047 -0.00798 -0.01366 C15 1 0.520890 0.142907 0.633947 11.00000 0.04308 0.04045 = 0.04216 0.00060 -0.00596 -0.01678 C16 1 0.662107 0.103108 0.693234 11.00000 0.04120 0.03299 = 0.03986 0.00303 -0.00741 -0.01245 C17 1 0.672599 -0.025300 0.760983 11.00000 0.05027 0.04123 = 0.05411 0.01178 -0.01316 -0.02210 AFIX 43 H17 2 0.592933 -0.081656 0.766267 11.00000 -1.20000 AFIX 0 C18 1 0.797970 -0.069608 0.819682 11.00000 0.05304 0.04370 = 0.05177 0.01785 -0.01363 -0.01531 AFIX 43 H18 2 0.802660 -0.155369 0.864700 11.00000 -1.20000 AFIX 0 C19 1 0.918000 0.011956 0.812755 11.00000 0.04221 0.03792 = 0.04304 -0.00071 -0.01227 -0.00661 C20 1 0.911310 0.138105 0.744717 11.00000 0.05309 0.04177 = 0.05425 0.01119 -0.01949 -0.02080 AFIX 43 H20 2 0.992660 0.192603 0.738248 11.00000 -1.20000 AFIX 0 C21 1 0.782866 0.182376 0.686525 11.00000 0.05823 0.03824 = 0.04763 0.01216 -0.01706 -0.01969 AFIX 43 H21 2 0.777994 0.268220 0.641557 11.00000 -1.20000 AFIX 0 C22 1 1.167501 0.032098 0.871567 11.00000 0.05157 0.07123 = 0.07948 0.00265 -0.02769 -0.01701 AFIX 137 H22A 2 1.224156 0.028699 0.804412 11.00000 -1.50000 H22B 2 1.243748 -0.022909 0.917011 11.00000 -1.50000 H22C 2 1.122802 0.140814 0.891125 11.00000 -1.50000 AFIX 0 N1 3 0.496275 0.277010 0.572102 11.00000 0.04019 0.03840 = 0.04207 0.00684 -0.01365 -0.01921 AFIX 43 H1N 2 0.562554 0.336654 0.570158 11.00000 -1.20000 AFIX 0 N2 3 0.345695 0.446509 0.455927 11.00000 0.04412 0.04364 = 0.04906 0.00823 -0.01697 -0.01889 N3 3 0.211167 0.463990 0.404202 11.00000 0.04521 0.04108 = 0.04772 0.00936 -0.01738 -0.01965 O1 4 -0.282433 0.593560 0.209464 11.00000 0.07512 0.03909 = 0.05273 -0.00198 -0.03033 -0.00229 O2 4 0.424663 0.059509 0.637504 11.00000 0.06078 0.05271 = 0.07072 0.02060 -0.02745 -0.03313 O3 4 1.037007 -0.042332 0.874752 11.00000 0.05418 0.05465 = 0.06342 0.01372 -0.02613 -0.01522 F1 5 -0.422485 0.342634 0.251773 11.00000 0.05651 0.08911 = 0.06643 0.00419 -0.03094 -0.02769 S1 6 0.229403 0.207966 0.509319 11.00000 0.04801 0.03770 = 0.04920 0.00705 -0.01700 -0.01920 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 -0.3077(4) 0.5400(5) -0.0924(2) 0.0670(10) Uani 1 1 d . . . H1 H -0.3140 0.5303 -0.1604 0.080 Uiso 1 1 calc R . . C2 C -0.4076(4) 0.6655(4) -0.0404(2) 0.0630(9) Uani 1 1 d . . . H2 H -0.4835 0.7422 -0.0733 0.076 Uiso 1 1 calc R . . C3 C -0.3993(4) 0.6820(3) 0.0600(2) 0.0539(8) Uani 1 1 d . . . H3 H -0.4683 0.7691 0.0947 0.065 Uiso 1 1 calc R . . C4 C -0.2877(3) 0.5678(3) 0.1082(2) 0.0427(7) Uani 1 1 d . . . C5 C -0.1857(4) 0.4397(4) 0.0579(2) 0.0603(9) Uani 1 1 d . . . H5 H -0.1103 0.3622 0.0907 0.072 Uiso 1 1 calc R . . C6 C -0.1973(4) 0.4280(5) -0.0429(2) 0.0765(11) Uani 1 1 d . . . H6 H -0.1281 0.3415 -0.0780 0.092 Uiso 1 1 calc R . . C7 C -0.2124(3) 0.4649(3) 0.26920(19) 0.0427(7) Uani 1 1 d . . . C8 C -0.2865(3) 0.3428(4) 0.29416(19) 0.0457(7) Uani 1 1 d . . . C9 C -0.2242(3) 0.2223(3) 0.3590(2) 0.0461(7) Uani 1 1 d . . . H9 H -0.2746 0.1401 0.3742 0.055 Uiso 1 1 calc R . . C10 C -0.0849(3) 0.2242(3) 0.40185(18) 0.0414(7) Uani 1 1 d . . . H10 H -0.0424 0.1432 0.4468 0.050 Uiso 1 1 calc R . . C11 C -0.0080(3) 0.3446(3) 0.37881(18) 0.0354(6) Uani 1 1 d . . . C12 C -0.0728(3) 0.4642(3) 0.31181(18) 0.0413(7) Uani 1 1 d . . . H12 H -0.0214 0.5455 0.2953 0.050 Uiso 1 1 calc R . . C13 C 0.1390(3) 0.3495(3) 0.42407(18) 0.0357(6) Uani 1 1 d . . . C14 C 0.3688(3) 0.3182(3) 0.51342(18) 0.0347(6) Uani 1 1 d . . . C15 C 0.5209(3) 0.1429(3) 0.63395(19) 0.0408(7) Uani 1 1 d . . . C16 C 0.6621(3) 0.1031(3) 0.69323(18) 0.0374(6) Uani 1 1 d . . . C17 C 0.6726(3) -0.0253(3) 0.76098(19) 0.0465(7) Uani 1 1 d . . . H17 H 0.5929 -0.0817 0.7663 0.056 Uiso 1 1 calc R . . C18 C 0.7980(3) -0.0696(3) 0.8197(2) 0.0491(8) Uani 1 1 d . . . H18 H 0.8027 -0.1554 0.8647 0.059 Uiso 1 1 calc R . . C19 C 0.9180(3) 0.0120(3) 0.81275(19) 0.0412(7) Uani 1 1 d . . . C20 C 0.9113(3) 0.1381(3) 0.7447(2) 0.0474(7) Uani 1 1 d . . . H20 H 0.9927 0.1926 0.7382 0.057 Uiso 1 1 calc R . . C21 C 0.7829(3) 0.1824(3) 0.68653(19) 0.0462(7) Uani 1 1 d . . . H21 H 0.7780 0.2682 0.6416 0.055 Uiso 1 1 calc R . . C22 C 1.1675(4) 0.0321(4) 0.8716(2) 0.0656(9) Uani 1 1 d . . . H22A H 1.2242 0.0287 0.8044 0.098 Uiso 1 1 calc R . . H22B H 1.2437 -0.0229 0.9170 0.098 Uiso 1 1 calc R . . H22C H 1.1228 0.1408 0.8911 0.098 Uiso 1 1 calc R . . N1 N 0.4963(2) 0.2770(2) 0.57210(14) 0.0380(5) Uani 1 1 d . . . H1N H 0.5626 0.3367 0.5702 0.046 Uiso 1 1 calc R . . N2 N 0.3457(3) 0.4465(3) 0.45593(16) 0.0435(6) Uani 1 1 d . . . N3 N 0.2112(3) 0.4640(3) 0.40420(15) 0.0424(6) Uani 1 1 d . . . O1 O -0.2824(2) 0.5936(2) 0.20946(13) 0.0560(6) Uani 1 1 d . . . O2 O 0.4247(2) 0.0595(2) 0.63750(14) 0.0569(6) Uani 1 1 d . . . O3 O 1.0370(2) -0.0423(2) 0.87475(14) 0.0561(6) Uani 1 1 d . . . F1 F -0.4225(2) 0.3426(2) 0.25177(12) 0.0671(5) Uani 1 1 d . . . S1 S 0.22940(9) 0.20797(8) 0.50932(5) 0.0427(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.066(2) 0.097(3) 0.044(2) 0.009(2) -0.0118(18) -0.031(2) C2 0.065(2) 0.075(2) 0.056(2) 0.0318(18) -0.0284(18) -0.028(2) C3 0.055(2) 0.0441(18) 0.063(2) 0.0125(15) -0.0191(16) -0.0098(16) C4 0.0466(17) 0.0441(17) 0.0441(18) 0.0073(14) -0.0199(14) -0.0182(15) C5 0.061(2) 0.060(2) 0.054(2) 0.0015(16) -0.0187(16) -0.0014(18) C6 0.072(2) 0.095(3) 0.054(2) -0.0161(19) -0.0096(19) -0.003(2) C7 0.0505(18) 0.0377(16) 0.0396(16) 0.0001(13) -0.0161(14) -0.0067(15) C8 0.0408(17) 0.0564(19) 0.0436(17) -0.0058(14) -0.0136(14) -0.0141(15) C9 0.0509(18) 0.0470(18) 0.0488(17) -0.0011(14) -0.0108(14) -0.0249(15) C10 0.0477(17) 0.0388(16) 0.0402(16) 0.0035(12) -0.0123(13) -0.0134(14) C11 0.0393(16) 0.0335(15) 0.0361(15) -0.0017(12) -0.0093(12) -0.0114(13) C12 0.0502(18) 0.0364(16) 0.0421(16) -0.0009(13) -0.0120(14) -0.0165(14) C13 0.0384(16) 0.0332(15) 0.0367(15) -0.0001(12) -0.0060(12) -0.0109(13) C14 0.0371(16) 0.0339(15) 0.0365(15) 0.0005(12) -0.0080(12) -0.0137(13) C15 0.0431(17) 0.0405(17) 0.0422(17) 0.0006(13) -0.0060(13) -0.0168(15) C16 0.0412(16) 0.0330(15) 0.0399(15) 0.0030(12) -0.0074(13) -0.0124(14) C17 0.0503(18) 0.0412(17) 0.0541(18) 0.0118(14) -0.0132(15) -0.0221(15) C18 0.0530(19) 0.0437(17) 0.0518(18) 0.0179(14) -0.0136(15) -0.0153(16) C19 0.0422(17) 0.0379(16) 0.0430(16) -0.0007(13) -0.0123(13) -0.0066(14) C20 0.0531(19) 0.0418(17) 0.0543(18) 0.0112(14) -0.0195(15) -0.0208(15) C21 0.0582(19) 0.0382(17) 0.0476(17) 0.0122(13) -0.0171(15) -0.0197(16) C22 0.052(2) 0.071(2) 0.079(2) 0.0027(18) -0.0277(17) -0.0170(19) N1 0.0402(13) 0.0384(13) 0.0421(13) 0.0068(10) -0.0136(11) -0.0192(11) N2 0.0441(14) 0.0436(14) 0.0491(14) 0.0082(11) -0.0170(11) -0.0189(12) N3 0.0452(14) 0.0411(14) 0.0477(14) 0.0094(10) -0.0174(11) -0.0197(12) O1 0.0751(15) 0.0391(12) 0.0527(13) -0.0020(9) -0.0303(11) -0.0023(11) O2 0.0608(13) 0.0527(13) 0.0707(14) 0.0206(10) -0.0274(11) -0.0331(12) O3 0.0542(13) 0.0546(13) 0.0634(13) 0.0137(10) -0.0261(10) -0.0152(11) F1 0.0565(11) 0.0891(14) 0.0664(11) 0.0042(9) -0.0309(9) -0.0277(10) S1 0.0480(5) 0.0377(4) 0.0492(5) 0.0071(3) -0.0170(3) -0.0192(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 C2 1.353(4) . ? C1 C6 1.366(4) . ? C1 H1 0.9300 . ? C2 C3 1.376(4) . ? C2 H2 0.9300 . ? C3 C4 1.372(4) . ? C3 H3 0.9300 . ? C4 C5 1.364(4) . ? C4 O1 1.398(3) . ? C5 C6 1.379(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C12 1.378(3) . ? C7 C8 1.381(4) . ? C7 O1 1.385(3) . ? C8 F1 1.350(3) . ? C8 C9 1.363(4) . ? C9 C10 1.383(3) . ? C9 H9 0.9300 . ? C10 C11 1.380(3) . ? C10 H10 0.9300 . ? C11 C12 1.383(3) . ? C11 C13 1.466(3) . ? C12 H12 0.9300 . ? C13 N3 1.304(3) . ? C13 S1 1.726(2) . ? C14 N2 1.307(3) . ? C14 N1 1.377(3) . ? C14 S1 1.721(2) . ? C15 O2 1.226(3) . ? C15 N1 1.380(3) . ? C15 C16 1.476(4) . ? C16 C21 1.372(3) . ? C16 C17 1.393(3) . ? C17 C18 1.364(4) . ? C17 H17 0.9300 . ? C18 C19 1.381(4) . ? C18 H18 0.9300 . ? C19 O3 1.360(3) . ? C19 C20 1.383(3) . ? C20 C21 1.380(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 O3 1.420(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? N1 H1N 0.8600 . ? N2 N3 1.380(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 C2 C1 C6 118.5(3) . . ? C2 C1 H1 120.7 . . ? C6 C1 H1 120.7 . . ? C1 C2 C3 121.5(3) . . ? C1 C2 H2 119.3 . . ? C3 C2 H2 119.3 . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C5 C4 C3 121.0(3) . . ? C5 C4 O1 122.8(2) . . ? C3 C4 O1 116.2(3) . . ? C4 C5 C6 118.3(3) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C1 C6 C5 121.8(3) . . ? C1 C6 H6 119.1 . . ? C5 C6 H6 119.1 . . ? C12 C7 C8 118.7(2) . . ? C12 C7 O1 119.4(2) . . ? C8 C7 O1 121.6(2) . . ? F1 C8 C9 119.7(2) . . ? F1 C8 C7 118.8(2) . . ? C9 C8 C7 121.6(2) . . ? C8 C9 C10 119.0(2) . . ? C8 C9 H9 120.5 . . ? C10 C9 H9 120.5 . . ? C11 C10 C9 121.0(2) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 118.8(2) . . ? C10 C11 C13 121.8(2) . . ? C12 C11 C13 119.4(2) . . ? C7 C12 C11 121.0(2) . . ? C7 C12 H12 119.5 . . ? C11 C12 H12 119.5 . . ? N3 C13 C11 122.4(2) . . ? N3 C13 S1 114.10(18) . . ? C11 C13 S1 123.48(19) . . ? N2 C14 N1 121.4(2) . . ? N2 C14 S1 114.99(18) . . ? N1 C14 S1 123.58(18) . . ? O2 C15 N1 118.7(2) . . ? O2 C15 C16 121.8(2) . . ? N1 C15 C16 119.4(2) . . ? C21 C16 C17 118.0(2) . . ? C21 C16 C15 125.1(2) . . ? C17 C16 C15 116.9(2) . . ? C18 C17 C16 121.0(3) . . ? C18 C17 H17 119.5 . . ? C16 C17 H17 119.5 . . ? C17 C18 C19 120.5(2) . . ? C17 C18 H18 119.8 . . ? C19 C18 H18 119.8 . . ? O3 C19 C18 115.5(2) . . ? O3 C19 C20 125.1(2) . . ? C18 C19 C20 119.4(2) . . ? C21 C20 C19 119.4(3) . . ? C21 C20 H20 120.3 . . ? C19 C20 H20 120.3 . . ? C16 C21 C20 121.8(2) . . ? C16 C21 H21 119.1 . . ? C20 C21 H21 119.1 . . ? O3 C22 H22A 109.5 . . ? O3 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O3 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C14 N1 C15 122.0(2) . . ? C14 N1 H1N 119.0 . . ? C15 N1 H1N 119.0 . . ? C14 N2 N3 111.4(2) . . ? C13 N3 N2 112.9(2) . . ? C7 O1 C4 118.3(2) . . ? C19 O3 C22 119.6(2) . . ? C14 S1 C13 86.63(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 0.3(5) . . . . ? C1 C2 C3 C4 -0.4(4) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? C2 C3 C4 O1 178.4(2) . . . . ? C3 C4 C5 C6 0.2(4) . . . . ? O1 C4 C5 C6 -178.0(3) . . . . ? C2 C1 C6 C5 0.1(5) . . . . ? C4 C5 C6 C1 -0.3(5) . . . . ? C12 C7 C8 F1 -179.4(2) . . . . ? O1 C7 C8 F1 6.0(4) . . . . ? C12 C7 C8 C9 -0.4(4) . . . . ? O1 C7 C8 C9 -175.0(2) . . . . ? F1 C8 C9 C10 -180.0(2) . . . . ? C7 C8 C9 C10 1.0(4) . . . . ? C8 C9 C10 C11 -0.8(4) . . . . ? C9 C10 C11 C12 0.0(4) . . . . ? C9 C10 C11 C13 179.5(2) . . . . ? C8 C7 C12 C11 -0.4(4) . . . . ? O1 C7 C12 C11 174.3(2) . . . . ? C10 C11 C12 C7 0.6(4) . . . . ? C13 C11 C12 C7 -178.9(2) . . . . ? C10 C11 C13 N3 -178.8(2) . . . . ? C12 C11 C13 N3 0.6(4) . . . . ? C10 C11 C13 S1 0.0(4) . . . . ? C12 C11 C13 S1 179.4(2) . . . . ? O2 C15 C16 C21 173.9(3) . . . . ? N1 C15 C16 C21 -5.6(4) . . . . ? O2 C15 C16 C17 -6.0(4) . . . . ? N1 C15 C16 C17 174.5(2) . . . . ? C21 C16 C17 C18 0.8(4) . . . . ? C15 C16 C17 C18 -179.3(3) . . . . ? C16 C17 C18 C19 -0.3(5) . . . . ? C17 C18 C19 O3 180.0(3) . . . . ? C17 C18 C19 C20 -0.8(4) . . . . ? O3 C19 C20 C21 -179.5(3) . . . . ? C18 C19 C20 C21 1.4(4) . . . . ? C17 C16 C21 C20 -0.2(4) . . . . ? C15 C16 C21 C20 179.9(3) . . . . ? C19 C20 C21 C16 -0.9(4) . . . . ? N2 C14 N1 C15 179.3(2) . . . . ? S1 C14 N1 C15 -0.8(3) . . . . ? O2 C15 N1 C14 -1.0(4) . . . . ? C16 C15 N1 C14 178.6(2) . . . . ? N1 C14 N2 N3 -179.9(2) . . . . ? S1 C14 N2 N3 0.1(3) . . . . ? C11 C13 N3 N2 179.1(2) . . . . ? S1 C13 N3 N2 0.2(3) . . . . ? C14 N2 N3 C13 -0.2(3) . . . . ? C12 C7 O1 C4 117.2(3) . . . . ? C8 C7 O1 C4 -68.3(3) . . . . ? C5 C4 O1 C7 -21.0(4) . . . . ? C3 C4 O1 C7 160.7(2) . . . . ? C18 C19 O3 C22 178.8(2) . . . . ? C20 C19 O3 C22 -0.4(4) . . . . ? N2 C14 S1 C13 0.0(2) . . . . ? N1 C14 S1 C13 -180.0(2) . . . . ? N3 C13 S1 C14 -0.1(2) . . . . ? C11 C13 S1 C14 -179.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.200 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.045