data_2443 _audit_creation_method 'SHELXL-2012 & ZCIF' _chemical_name_systematic ; Ta-complex, AK-747 ; _chemical_name_common Ta-complex _chemical_formula_moiety 'C20 H36 F3 N4 O3 S Ta' _chemical_formula_sum 'C20 H36 F3 N4 O3 S Ta' _chemical_formula_weight 650.54 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' 'Ta' 'Ta' -0.7052 6.5227 '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' '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' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/n' _space_group_name_Hall '-P 2yn' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9723(18) _cell_length_b 22.562(4) _cell_length_c 11.833(2) _cell_angle_alpha 90 _cell_angle_beta 104.635(3) _cell_angle_gamma 90 _cell_volume 2575.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12964 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 31.5 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_density_diffrn 1.677 _exptl_crystal_F_000 1296 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.025 _exptl_absorpt_coefficient_mu 4.397 _shelx_estimated_absorpt_T_min 0.505 _shelx_estimated_absorpt_T_max 0.898 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.699 _exptl_absorpt_correction_T_max 0.896 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'sealed tube' _diffrn_measurement_device_type 'Bruker Smart Apex II diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_reflns_number 35383 _diffrn_reflns_av_unetI/netI 0.0233 _diffrn_reflns_av_R_equivalents 0.0353 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.805 _diffrn_reflns_theta_max 27.498 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_point_group_measured_fraction_full 1.000 _reflns_number_total 5906 _reflns_number_gt 5218 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'Apex2 (Bruker, 2010)' _computing_cell_refinement Apex2 _computing_data_reduction 'Apex2, Saint' _computing_structure_solution 'ShelXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'ShelXL-2012 (Sheldrick, 2012)' _computing_molecular_graphics 'XSHEL (Bruker, 2004)' _computing_publication_material 'Apex2, SHELXL-2012' _refine_special_details ; H atoms in CH and CH3 groups were refined as riding on the attached atom with Uiso refined but constrained to be the same within CH3 group. H atom in N-H group was located from difference Fourier map and freely refined. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0100P)^2^+4.3000P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens mixed _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 5906 _refine_ls_number_parameters 316 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0270 _refine_ls_R_factor_gt 0.0210 _refine_ls_wR_factor_ref 0.0421 _refine_ls_wR_factor_gt 0.0399 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Ta1 Ta 0.28136(2) 0.10031(2) 0.27755(2) 0.01807(3) Uani 1 1 d . . . . . N1 N 0.4510(3) 0.07335(11) 0.3385(2) 0.0262(5) Uani 1 1 d . . . . . H1 H 0.510(4) 0.0518(18) 0.369(4) 0.066(14) Uiso 1 1 d . . . . . O1 O 0.24697(19) 0.11766(8) 0.44802(16) 0.0245(4) Uani 1 1 d . . . . . O2 O 0.4537(2) 0.15768(11) 0.5824(2) 0.0482(6) Uani 1 1 d . . . . . O3 O 0.3940(3) 0.05302(11) 0.5929(2) 0.0504(7) Uani 1 1 d . . . . . S1 S 0.35149(8) 0.11242(3) 0.56240(6) 0.02985(16) Uani 1 1 d . . . . . C1 C 0.2427(4) 0.13031(15) 0.6608(3) 0.0401(8) Uani 1 1 d . . . . . F1 F 0.3187(3) 0.12897(11) 0.77089(17) 0.0623(6) Uani 1 1 d . . . . . F2 F 0.1879(3) 0.18352(10) 0.6411(2) 0.0625(6) Uani 1 1 d . . . . . F3 F 0.1401(2) 0.09188(11) 0.6507(2) 0.0629(6) Uani 1 1 d . . . . . N11 N 0.2413(2) 0.19680(10) 0.2609(2) 0.0236(5) Uani 1 1 d . . . . . N12 N 0.3301(2) 0.14731(10) 0.1360(2) 0.0232(5) Uani 1 1 d . . . . . C10 C 0.2808(3) 0.20013(12) 0.1620(2) 0.0231(5) Uani 1 1 d . . . . . N13 N 0.2746(3) 0.24858(11) 0.0904(2) 0.0366(6) Uani 1 1 d . . . . . C11 C 0.3045(4) 0.30906(14) 0.1318(4) 0.0474(9) Uani 1 1 d . . . . . H11A H 0.2177 0.3314 0.1196 0.050(6) Uiso 1 1 calc R . . . . H11B H 0.3646 0.3280 0.0885 0.050(6) Uiso 1 1 calc R . . . . H11C H 0.3514 0.3085 0.2153 0.050(6) Uiso 1 1 calc R . . . . C12 C 0.2220(4) 0.24237(17) -0.0352(3) 0.0478(9) Uani 1 1 d . . . . . H12A H 0.2068 0.2003 -0.0551 0.056(6) Uiso 1 1 calc R . . . . H12B H 0.2895 0.2587 -0.0744 0.056(6) Uiso 1 1 calc R . . . . H12C H 0.1342 0.2639 -0.0609 0.056(6) Uiso 1 1 calc R . . . . C13 C 0.1611(3) 0.24444(12) 0.2995(3) 0.0286(6) Uani 1 1 d . . . . . H13 H 0.1364 0.2747 0.2359 0.024(5) Uiso 1 1 calc R . . . . C14 C 0.0278(3) 0.22136(14) 0.3235(3) 0.0376(8) Uani 1 1 d . . . . . H14A H -0.0295 0.2030 0.2525 0.040(5) Uiso 1 1 calc R . . . . H14B H -0.0231 0.2543 0.3471 0.040(5) Uiso 1 1 calc R . . . . H14C H 0.0500 0.1919 0.3862 0.040(5) Uiso 1 1 calc R . . . . C15 C 0.2502(4) 0.27412(14) 0.4076(3) 0.0408(8) Uani 1 1 d . . . . . H15A H 0.2746 0.2452 0.4713 0.053(6) Uiso 1 1 calc R . . . . H15B H 0.1986 0.3070 0.4308 0.053(6) Uiso 1 1 calc R . . . . H15C H 0.3349 0.2894 0.3905 0.053(6) Uiso 1 1 calc R . . . . C16 C 0.4596(3) 0.14939(13) 0.0945(3) 0.0297(6) Uani 1 1 d . . . . . H16 H 0.4401 0.1731 0.0207 0.024(5) Uiso 1 1 calc R . . . . C17 C 0.5062(3) 0.08813(14) 0.0683(3) 0.0394(8) Uani 1 1 d . . . . . H17A H 0.5199 0.0633 0.1382 0.045(6) Uiso 1 1 calc R . . . . H17B H 0.5935 0.0912 0.0450 0.045(6) Uiso 1 1 calc R . . . . H17C H 0.4353 0.0703 0.0047 0.045(6) Uiso 1 1 calc R . . . . C18 C 0.5757(3) 0.18016(14) 0.1842(3) 0.0365(7) Uani 1 1 d . . . . . H18A H 0.5455 0.2199 0.2000 0.044(6) Uiso 1 1 calc R . . . . H18B H 0.6580 0.1832 0.1536 0.044(6) Uiso 1 1 calc R . . . . H18C H 0.5983 0.1571 0.2567 0.044(6) Uiso 1 1 calc R . . . . C20 C 0.0466(3) 0.07405(12) 0.1475(3) 0.0254(6) Uani 1 1 d . . . . . C21 C 0.0510(3) 0.05212(12) 0.2602(3) 0.0260(6) Uani 1 1 d . . . . . C22 C 0.1595(3) 0.00927(11) 0.2895(2) 0.0257(6) Uani 1 1 d . . . . . C23 C 0.2176(3) 0.00283(11) 0.1926(2) 0.0248(6) Uani 1 1 d . . . . . C24 C 0.1486(3) 0.04303(12) 0.1051(2) 0.0253(6) Uani 1 1 d . . . . . C25 C -0.0530(3) 0.11738(14) 0.0754(3) 0.0399(8) Uani 1 1 d . . . . . H25A H -0.1246 0.1274 0.1157 0.062(7) Uiso 1 1 calc R . . . . H25B H -0.0965 0.0997 -0.0006 0.062(7) Uiso 1 1 calc R . . . . H25C H -0.0032 0.1534 0.0640 0.062(7) Uiso 1 1 calc R . . . . C26 C -0.0481(3) 0.06612(15) 0.3338(3) 0.0413(8) Uani 1 1 d . . . . . H26A H -0.1054 0.1002 0.3005 0.066(7) Uiso 1 1 calc R . . . . H26B H 0.0044 0.0755 0.4136 0.066(7) Uiso 1 1 calc R . . . . H26C H -0.1077 0.0318 0.3351 0.066(7) Uiso 1 1 calc R . . . . C27 C 0.1931(4) -0.02823(13) 0.3976(3) 0.0390(8) Uani 1 1 d . . . . . H27A H 0.1316 -0.0628 0.3860 0.049(6) Uiso 1 1 calc R . . . . H27B H 0.1798 -0.0049 0.4638 0.049(6) Uiso 1 1 calc R . . . . H27C H 0.2896 -0.0415 0.4136 0.049(6) Uiso 1 1 calc R . . . . C28 C 0.3245(3) -0.04267(13) 0.1827(3) 0.0368(8) Uani 1 1 d . . . . . H28A H 0.3961 -0.0447 0.2565 0.056(6) Uiso 1 1 calc R . . . . H28B H 0.3670 -0.0314 0.1196 0.056(6) Uiso 1 1 calc R . . . . H28C H 0.2800 -0.0815 0.1654 0.056(6) Uiso 1 1 calc R . . . . C29 C 0.1615(3) 0.04743(14) -0.0180(3) 0.0370(7) Uani 1 1 d . . . . . H29A H 0.0718 0.0387 -0.0721 0.038(5) Uiso 1 1 calc R . . . . H29B H 0.2307 0.0189 -0.0299 0.038(5) Uiso 1 1 calc R . . . . H29C H 0.1905 0.0876 -0.0325 0.038(5) 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 Ta1 0.01722(5) 0.01672(5) 0.01958(6) -0.00183(4) 0.00337(4) 0.00013(4) N1 0.0233(13) 0.0296(13) 0.0243(13) -0.0014(10) 0.0035(10) 0.0042(10) O1 0.0246(10) 0.0256(9) 0.0225(10) -0.0008(8) 0.0047(8) 0.0046(8) O2 0.0348(13) 0.0675(17) 0.0398(14) -0.0148(12) 0.0047(11) -0.0142(12) O3 0.0626(17) 0.0449(14) 0.0333(13) -0.0005(11) -0.0069(12) 0.0274(12) S1 0.0284(4) 0.0356(4) 0.0229(4) -0.0036(3) 0.0016(3) 0.0060(3) C1 0.051(2) 0.0413(18) 0.0301(17) -0.0030(14) 0.0136(16) 0.0017(16) F1 0.0768(16) 0.0843(16) 0.0247(11) -0.0071(11) 0.0104(11) 0.0026(13) F2 0.0885(17) 0.0535(13) 0.0572(14) -0.0009(11) 0.0400(13) 0.0273(12) F3 0.0661(15) 0.0771(16) 0.0543(14) -0.0031(12) 0.0313(12) -0.0228(13) N11 0.0233(12) 0.0207(11) 0.0278(12) -0.0022(9) 0.0084(10) -0.0010(9) N12 0.0225(12) 0.0242(11) 0.0240(12) -0.0013(9) 0.0078(10) -0.0029(9) C10 0.0205(13) 0.0214(12) 0.0270(14) 0.0011(11) 0.0054(11) -0.0037(11) N13 0.0427(16) 0.0276(13) 0.0419(16) 0.0094(11) 0.0152(13) -0.0004(11) C11 0.045(2) 0.0259(16) 0.079(3) 0.0116(17) 0.0293(19) -0.0017(14) C12 0.049(2) 0.059(2) 0.039(2) 0.0241(17) 0.0187(17) 0.0077(18) C13 0.0310(16) 0.0195(13) 0.0366(17) -0.0017(12) 0.0111(13) 0.0046(11) C14 0.0321(17) 0.0309(16) 0.054(2) -0.0009(15) 0.0197(16) 0.0060(13) C15 0.049(2) 0.0267(15) 0.048(2) -0.0131(14) 0.0154(17) 0.0008(14) C16 0.0301(16) 0.0346(16) 0.0292(16) -0.0008(13) 0.0162(13) -0.0014(12) C17 0.0333(17) 0.0464(19) 0.042(2) -0.0145(15) 0.0168(15) -0.0001(14) C18 0.0262(16) 0.0390(17) 0.049(2) -0.0065(15) 0.0176(14) -0.0065(13) C20 0.0197(14) 0.0206(13) 0.0310(16) -0.0007(11) -0.0029(11) -0.0067(10) C21 0.0211(14) 0.0224(13) 0.0345(16) -0.0030(11) 0.0073(12) -0.0072(11) C22 0.0287(15) 0.0182(12) 0.0282(15) -0.0009(11) 0.0034(12) -0.0050(11) C23 0.0263(14) 0.0181(12) 0.0283(15) -0.0056(11) 0.0037(12) -0.0032(11) C24 0.0256(14) 0.0220(13) 0.0248(15) -0.0040(11) -0.0003(11) -0.0083(11) C25 0.0285(16) 0.0336(16) 0.047(2) 0.0009(14) -0.0106(14) 0.0012(13) C26 0.0341(18) 0.0392(18) 0.058(2) -0.0068(16) 0.0243(17) -0.0082(14) C27 0.051(2) 0.0275(15) 0.0379(19) 0.0062(14) 0.0089(16) -0.0034(14) C28 0.0384(18) 0.0261(15) 0.0416(19) -0.0130(13) 0.0022(15) 0.0063(13) C29 0.0435(19) 0.0400(17) 0.0240(16) -0.0042(13) 0.0021(14) -0.0141(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 Ta1 N1 1.771(3) . ? Ta1 N12 2.139(2) . ? Ta1 O1 2.1655(19) . ? Ta1 N11 2.213(2) . ? Ta1 C22 2.409(3) . ? Ta1 C23 2.435(3) . ? Ta1 C24 2.495(3) . ? Ta1 C21 2.503(3) . ? Ta1 C20 2.525(3) . ? N1 H1 0.78(4) . ? O1 S1 1.490(2) . ? O2 S1 1.420(2) . ? O3 S1 1.424(2) . ? S1 C1 1.826(3) . ? C1 F2 1.315(4) . ? C1 F3 1.323(4) . ? C1 F1 1.332(4) . ? N11 C10 1.328(3) . ? N11 C13 1.480(3) . ? N12 C10 1.353(3) . ? N12 C16 1.494(3) . ? C10 N13 1.375(3) . ? N13 C12 1.452(4) . ? N13 C11 1.455(4) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 C15 1.516(4) . ? C13 C14 1.519(4) . ? C13 H13 1.0000 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 C17 1.515(4) . ? C16 C18 1.526(4) . ? C16 H16 1.0000 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C20 C21 1.412(4) . ? C20 C24 1.426(4) . ? C20 C25 1.498(4) . ? C21 C22 1.427(4) . ? C21 C26 1.506(4) . ? C22 C23 1.416(4) . ? C22 C27 1.499(4) . ? C23 C24 1.418(4) . ? C23 C28 1.506(4) . ? C24 C29 1.498(4) . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 H28A 0.9800 . ? C28 H28B 0.9800 . ? C28 H28C 0.9800 . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? 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 N1 Ta1 N12 96.11(10) . . ? N1 Ta1 O1 92.45(9) . . ? N12 Ta1 O1 139.50(8) . . ? N1 Ta1 N11 120.42(10) . . ? N12 Ta1 N11 60.94(8) . . ? O1 Ta1 N11 80.65(8) . . ? N1 Ta1 C22 97.32(11) . . ? N12 Ta1 C22 133.34(9) . . ? O1 Ta1 C22 84.18(8) . . ? N11 Ta1 C22 139.62(9) . . ? N1 Ta1 C23 88.89(10) . . ? N12 Ta1 C23 102.24(9) . . ? O1 Ta1 C23 117.48(8) . . ? N11 Ta1 C23 146.05(9) . . ? C22 Ta1 C23 34.00(9) . . ? N1 Ta1 C24 114.22(10) . . ? N12 Ta1 C24 78.18(9) . . ? O1 Ta1 C24 132.79(8) . . ? N11 Ta1 C24 112.98(9) . . ? C22 Ta1 C24 55.58(9) . . ? C23 Ta1 C24 33.40(9) . . ? N1 Ta1 C21 130.31(11) . . ? N12 Ta1 C21 122.45(9) . . ? O1 Ta1 C21 78.27(8) . . ? N11 Ta1 C21 106.19(9) . . ? C22 Ta1 C21 33.71(9) . . ? C23 Ta1 C21 55.62(9) . . ? C24 Ta1 C21 54.64(9) . . ? N1 Ta1 C20 144.16(10) . . ? N12 Ta1 C20 89.91(9) . . ? O1 Ta1 C20 105.62(9) . . ? N11 Ta1 C20 93.33(8) . . ? C22 Ta1 C20 55.39(9) . . ? C23 Ta1 C20 55.36(9) . . ? C24 Ta1 C20 33.00(9) . . ? C21 Ta1 C20 32.63(9) . . ? Ta1 N1 H1 160(3) . . ? S1 O1 Ta1 126.36(11) . . ? O2 S1 O3 118.62(16) . . ? O2 S1 O1 113.75(13) . . ? O3 S1 O1 113.59(13) . . ? O2 S1 C1 104.58(15) . . ? O3 S1 C1 103.49(16) . . ? O1 S1 C1 99.77(14) . . ? F2 C1 F3 107.7(3) . . ? F2 C1 F1 107.6(3) . . ? F3 C1 F1 108.0(3) . . ? F2 C1 S1 112.1(2) . . ? F3 C1 S1 111.6(2) . . ? F1 C1 S1 109.6(2) . . ? C10 N11 C13 122.3(2) . . ? C10 N11 Ta1 92.69(16) . . ? C13 N11 Ta1 141.88(18) . . ? C10 N12 C16 116.1(2) . . ? C10 N12 Ta1 95.26(16) . . ? C16 N12 Ta1 131.25(18) . . ? N11 C10 N12 110.8(2) . . ? N11 C10 N13 127.7(3) . . ? N12 C10 N13 121.5(3) . . ? C10 N13 C12 120.1(3) . . ? C10 N13 C11 124.3(3) . . ? C12 N13 C11 115.2(3) . . ? N13 C11 H11A 109.5 . . ? N13 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? N13 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N13 C12 H12A 109.5 . . ? N13 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? N13 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N11 C13 C15 109.5(2) . . ? N11 C13 C14 112.1(2) . . ? C15 C13 C14 110.4(3) . . ? N11 C13 H13 108.3 . . ? C15 C13 H13 108.3 . . ? C14 C13 H13 108.3 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N12 C16 C17 112.0(2) . . ? N12 C16 C18 110.6(2) . . ? C17 C16 C18 109.8(3) . . ? N12 C16 H16 108.1 . . ? C17 C16 H16 108.1 . . ? C18 C16 H16 108.1 . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C18 H18A 109.5 . . ? C16 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C16 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C21 C20 C24 107.8(2) . . ? C21 C20 C25 128.6(3) . . ? C24 C20 C25 123.3(3) . . ? C21 C20 Ta1 72.80(15) . . ? C24 C20 Ta1 72.31(15) . . ? C25 C20 Ta1 124.99(18) . . ? C20 C21 C22 107.9(2) . . ? C20 C21 C26 127.1(3) . . ? C22 C21 C26 124.8(3) . . ? C20 C21 Ta1 74.58(15) . . ? C22 C21 Ta1 69.53(15) . . ? C26 C21 Ta1 125.8(2) . . ? C23 C22 C21 108.3(2) . . ? C23 C22 C27 125.7(3) . . ? C21 C22 C27 125.5(3) . . ? C23 C22 Ta1 74.01(15) . . ? C21 C22 Ta1 76.76(15) . . ? C27 C22 Ta1 121.61(19) . . ? C22 C23 C24 107.6(2) . . ? C22 C23 C28 125.1(3) . . ? C24 C23 C28 127.0(3) . . ? C22 C23 Ta1 72.00(14) . . ? C24 C23 Ta1 75.62(15) . . ? C28 C23 Ta1 122.15(19) . . ? C23 C24 C20 108.3(2) . . ? C23 C24 C29 127.4(3) . . ? C20 C24 C29 123.7(3) . . ? C23 C24 Ta1 70.98(15) . . ? C20 C24 Ta1 74.69(15) . . ? C29 C24 Ta1 127.07(19) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C21 C26 H26A 109.5 . . ? C21 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C21 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C22 C27 H27A 109.5 . . ? C22 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C22 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C23 C28 H28A 109.5 . . ? C23 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C23 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C29 H29A 109.5 . . ? C24 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C24 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 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 Ta1 O1 S1 O2 71.89(17) . . . . ? Ta1 O1 S1 O3 -67.85(19) . . . . ? Ta1 O1 S1 C1 -177.32(15) . . . . ? O2 S1 C1 F2 58.2(3) . . . . ? O3 S1 C1 F2 -177.0(2) . . . . ? O1 S1 C1 F2 -59.6(3) . . . . ? O2 S1 C1 F3 179.2(2) . . . . ? O3 S1 C1 F3 -56.0(3) . . . . ? O1 S1 C1 F3 61.3(3) . . . . ? O2 S1 C1 F1 -61.2(3) . . . . ? O3 S1 C1 F1 63.6(3) . . . . ? O1 S1 C1 F1 -179.1(2) . . . . ? C13 N11 C10 N12 -169.0(2) . . . . ? Ta1 N11 C10 N12 -4.8(2) . . . . ? C13 N11 C10 N13 10.5(4) . . . . ? Ta1 N11 C10 N13 174.6(3) . . . . ? C16 N12 C10 N11 -136.5(2) . . . . ? Ta1 N12 C10 N11 5.0(2) . . . . ? C16 N12 C10 N13 44.1(4) . . . . ? Ta1 N12 C10 N13 -174.4(2) . . . . ? N11 C10 N13 C12 -134.4(3) . . . . ? N12 C10 N13 C12 45.0(4) . . . . ? N11 C10 N13 C11 39.0(5) . . . . ? N12 C10 N13 C11 -141.6(3) . . . . ? C10 N11 C13 C15 -112.0(3) . . . . ? Ta1 N11 C13 C15 94.2(3) . . . . ? C10 N11 C13 C14 125.1(3) . . . . ? Ta1 N11 C13 C14 -28.6(4) . . . . ? C10 N12 C16 C17 179.8(3) . . . . ? Ta1 N12 C16 C17 55.3(3) . . . . ? C10 N12 C16 C18 57.0(3) . . . . ? Ta1 N12 C16 C18 -67.5(3) . . . . ? C24 C20 C21 C22 2.4(3) . . . . ? C25 C20 C21 C22 176.6(3) . . . . ? Ta1 C20 C21 C22 -61.95(18) . . . . ? C24 C20 C21 C26 -172.2(3) . . . . ? C25 C20 C21 C26 2.1(5) . . . . ? Ta1 C20 C21 C26 123.5(3) . . . . ? C24 C20 C21 Ta1 64.31(18) . . . . ? C25 C20 C21 Ta1 -121.4(3) . . . . ? C20 C21 C22 C23 -2.7(3) . . . . ? C26 C21 C22 C23 172.1(3) . . . . ? Ta1 C21 C22 C23 -67.93(18) . . . . ? C20 C21 C22 C27 -175.2(3) . . . . ? C26 C21 C22 C27 -0.4(4) . . . . ? Ta1 C21 C22 C27 119.6(3) . . . . ? C20 C21 C22 Ta1 65.25(18) . . . . ? C26 C21 C22 Ta1 -120.0(3) . . . . ? C21 C22 C23 C24 2.0(3) . . . . ? C27 C22 C23 C24 174.4(3) . . . . ? Ta1 C22 C23 C24 -67.83(18) . . . . ? C21 C22 C23 C28 -173.1(3) . . . . ? C27 C22 C23 C28 -0.7(4) . . . . ? Ta1 C22 C23 C28 117.1(3) . . . . ? C21 C22 C23 Ta1 69.78(18) . . . . ? C27 C22 C23 Ta1 -117.7(3) . . . . ? C22 C23 C24 C20 -0.5(3) . . . . ? C28 C23 C24 C20 174.5(3) . . . . ? Ta1 C23 C24 C20 -65.89(18) . . . . ? C22 C23 C24 C29 -172.0(3) . . . . ? C28 C23 C24 C29 3.0(5) . . . . ? Ta1 C23 C24 C29 122.6(3) . . . . ? C22 C23 C24 Ta1 65.40(18) . . . . ? C28 C23 C24 Ta1 -119.6(3) . . . . ? C21 C20 C24 C23 -1.2(3) . . . . ? C25 C20 C24 C23 -175.8(2) . . . . ? Ta1 C20 C24 C23 63.47(18) . . . . ? C21 C20 C24 C29 170.7(2) . . . . ? C25 C20 C24 C29 -3.9(4) . . . . ? Ta1 C20 C24 C29 -124.6(3) . . . . ? C21 C20 C24 Ta1 -64.63(18) . . . . ? C25 C20 C24 Ta1 120.7(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.78(4) 2.55(4) 3.247(3) 150(4) 3_656 _refine_diff_density_max 0.715 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.087 _diffrn_radiation_monochromator graphite _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/n _diffrn_orient_matrix_type standard _diffrn_orient_matrix_UB_11 0.0785402 _diffrn_orient_matrix_UB_12 0.0101189 _diffrn_orient_matrix_UB_13 -0.0349066 _diffrn_orient_matrix_UB_21 0.0592421 _diffrn_orient_matrix_UB_22 0.0097028 _diffrn_orient_matrix_UB_23 0.0794545 _diffrn_orient_matrix_UB_31 0.0325957 _diffrn_orient_matrix_UB_32 -0.0420474 _diffrn_orient_matrix_UB_33 0.0098776 _diffrn_measurement_specimen_support 'MiTeGen loop' _diffrn_detector 'CCD area detector' _iucr_refine_instructions_details 'See _shelx_res_file' #_______________________________________________________________________________ # _publ_section_references ; Bruker (2010). Apex2. Bruker AXS Inc., Madison, Wisconsin, USA. Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122. Sheldrick, G. M. (2012). SHELXL-2012. University of G\"ottingen, Germany. ;