Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_section_title ;Reactivity of Niobium(V) and Tantalum(V) Halides with Carbonyl Compounds: Synthesis of Simple Coordination Adducts, C-H bond Activation, C=O Protonation, and Halide Transfer ; _publ_contact_author_name 'Guido Pampaloni' _publ_contact_author_email PAMPA@DCCI.UNIPI.IT loop_ _publ_author_name G.Pampaloni F.Marchetti S.Zacchini # Attachment 'TaCl4_C6H11O2_.CIF' data_tacl _database_code_depnum_ccdc_archive 'CCDC 649831' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H11 Cl4 O2 Ta' _chemical_formula_weight 437.90 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.7058(12) _cell_length_b 15.462(3) _cell_length_c 12.189(2) _cell_angle_alpha 90.00 _cell_angle_beta 102.753(2) _cell_angle_gamma 90.00 _cell_volume 1232.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5147 _cell_measurement_theta_min 2.6345 _cell_measurement_theta_max 28.456 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 9.752 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2031 _exptl_absorpt_correction_T_max 0.3045 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13011 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0280 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2700 _reflns_number_gt 2597 _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^)+(0.0285P)^2^+1.9818P] 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 2700 _refine_ls_number_parameters 121 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0231 _refine_ls_R_factor_gt 0.0221 _refine_ls_wR_factor_ref 0.0583 _refine_ls_wR_factor_gt 0.0577 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.116 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ta1 Ta 0.68689(2) -0.083958(8) 0.229565(11) 0.01421(7) Uani 1 1 d . . . Cl1 Cl 0.37288(13) -0.01289(6) 0.16488(8) 0.02307(19) Uani 1 1 d . . . Cl2 Cl 0.56670(15) -0.17801(6) 0.34513(8) 0.02498(19) Uani 1 1 d . . . Cl3 Cl 0.60314(14) -0.16511(6) 0.06047(8) 0.02420(19) Uani 1 1 d . . . Cl4 Cl 1.01266(14) -0.14687(6) 0.26330(9) 0.0259(2) Uani 1 1 d . . . O1 O 0.8164(4) 0.00444(15) 0.1231(2) 0.0164(5) Uani 1 1 d . . . O2 O 0.7715(4) 0.00367(16) 0.3307(2) 0.0184(5) Uani 1 1 d . . . C1 C 0.8450(6) 0.0838(2) 0.1337(3) 0.0187(7) Uani 1 1 d . . . C2 C 0.7680(6) 0.1334(2) 0.2213(3) 0.0211(7) Uani 1 1 d . . . H2A H 0.6170 0.1363 0.1991 0.025 Uiso 1 1 calc R . . H2B H 0.8208 0.1933 0.2236 0.025 Uiso 1 1 calc R . . C3 C 0.8294(6) 0.0944(2) 0.3393(4) 0.0215(8) Uani 1 1 d . . . C4 C 0.9570(6) 0.1293(2) 0.0585(3) 0.0237(8) Uani 1 1 d . . . H4A H 0.9981 0.0875 0.0072 0.035 Uiso 1 1 calc R . . H4B H 1.0788 0.1573 0.1038 0.035 Uiso 1 1 calc R . . H4C H 0.8679 0.1732 0.0148 0.035 Uiso 1 1 calc R . . C5 C 1.0590(7) 0.0984(3) 0.3856(4) 0.0299(9) Uani 1 1 d . . . H5A H 1.0924 0.0721 0.4605 0.045 Uiso 1 1 calc R . . H5B H 1.1036 0.1589 0.3907 0.045 Uiso 1 1 calc R . . H5C H 1.1290 0.0669 0.3353 0.045 Uiso 1 1 calc R . . C6 C 0.7105(8) 0.1363(3) 0.4175(4) 0.0363(10) Uani 1 1 d . . . H6A H 0.5642 0.1248 0.3900 0.054 Uiso 1 1 calc R . . H6B H 0.7345 0.1988 0.4198 0.054 Uiso 1 1 calc R . . H6C H 0.7558 0.1122 0.4933 0.054 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 0.01445(9) 0.01220(10) 0.01458(10) 0.00013(4) 0.00022(6) -0.00114(4) Cl1 0.0158(4) 0.0239(4) 0.0270(5) 0.0026(3) -0.0005(3) 0.0017(3) Cl2 0.0274(4) 0.0242(4) 0.0218(4) 0.0068(3) 0.0021(4) -0.0070(4) Cl3 0.0279(5) 0.0230(4) 0.0212(4) -0.0080(3) 0.0044(4) -0.0073(3) Cl4 0.0186(4) 0.0185(4) 0.0386(5) 0.0041(4) 0.0024(4) 0.0045(3) O1 0.0167(12) 0.0156(12) 0.0155(12) 0.0015(9) 0.0003(10) -0.0015(9) O2 0.0217(12) 0.0163(12) 0.0153(12) -0.0018(9) 0.0001(10) -0.0024(9) C1 0.0153(17) 0.0172(18) 0.0203(19) 0.0051(12) -0.0034(15) 0.0005(12) C2 0.0225(18) 0.0117(16) 0.028(2) 0.0013(14) 0.0023(16) 0.0022(13) C3 0.024(2) 0.0165(18) 0.023(2) -0.0070(13) 0.0028(16) -0.0028(13) C4 0.0211(18) 0.0213(18) 0.027(2) 0.0052(15) 0.0024(16) -0.0028(14) C5 0.025(2) 0.032(2) 0.029(2) -0.0023(17) -0.0035(18) -0.0093(16) C6 0.046(3) 0.030(2) 0.035(2) -0.0129(18) 0.013(2) 0.0014(19) _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 O2 1.835(2) . ? Ta1 O1 2.192(2) . ? Ta1 Cl2 2.2913(9) . ? Ta1 Cl4 2.3433(9) . ? Ta1 Cl1 2.3516(9) . ? Ta1 Cl3 2.3722(9) . ? O1 C1 1.244(4) . ? O2 C3 1.453(4) . ? C1 C4 1.484(5) . ? C1 C2 1.495(5) . ? C2 C3 1.531(6) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C6 1.516(6) . ? C3 C5 1.519(6) . ? C4 H4A 0.9800 . ? C4 H4B 0.9800 . ? C4 H4C 0.9800 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 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 O2 Ta1 O1 80.38(10) . . ? O2 Ta1 Cl2 98.88(8) . . ? O1 Ta1 Cl2 177.32(7) . . ? O2 Ta1 Cl4 92.90(9) . . ? O1 Ta1 Cl4 83.50(7) . . ? Cl2 Ta1 Cl4 93.98(4) . . ? O2 Ta1 Cl1 90.08(8) . . ? O1 Ta1 Cl1 87.28(7) . . ? Cl2 Ta1 Cl1 95.29(4) . . ? Cl4 Ta1 Cl1 169.70(3) . . ? O2 Ta1 Cl3 162.33(8) . . ? O1 Ta1 Cl3 82.20(7) . . ? Cl2 Ta1 Cl3 98.66(4) . . ? Cl4 Ta1 Cl3 88.03(4) . . ? Cl1 Ta1 Cl3 86.17(3) . . ? C1 O1 Ta1 128.7(2) . . ? C3 O2 Ta1 143.1(2) . . ? O1 C1 C4 119.4(3) . . ? O1 C1 C2 120.7(3) . . ? C4 C1 C2 120.0(3) . . ? C1 C2 C3 113.9(3) . . ? C1 C2 H2A 108.8 . . ? C3 C2 H2A 108.8 . . ? C1 C2 H2B 108.8 . . ? C3 C2 H2B 108.8 . . ? H2A C2 H2B 107.7 . . ? O2 C3 C6 106.8(3) . . ? O2 C3 C5 107.4(3) . . ? C6 C3 C5 112.3(4) . . ? O2 C3 C2 107.4(3) . . ? C6 C3 C2 110.7(3) . . ? C5 C3 C2 111.9(3) . . ? C1 C4 H4A 109.5 . . ? C1 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C1 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 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 O2 Ta1 O1 C1 -22.4(3) . . . . ? Cl2 Ta1 O1 C1 -96.6(14) . . . . ? Cl4 Ta1 O1 C1 -116.5(3) . . . . ? Cl1 Ta1 O1 C1 68.1(3) . . . . ? Cl3 Ta1 O1 C1 154.6(3) . . . . ? O1 Ta1 O2 C3 19.0(4) . . . . ? Cl2 Ta1 O2 C3 -163.6(4) . . . . ? Cl4 Ta1 O2 C3 101.9(4) . . . . ? Cl1 Ta1 O2 C3 -68.2(4) . . . . ? Cl3 Ta1 O2 C3 9.3(6) . . . . ? Ta1 O1 C1 C4 173.1(2) . . . . ? Ta1 O1 C1 C2 -6.8(5) . . . . ? O1 C1 C2 C3 51.0(5) . . . . ? C4 C1 C2 C3 -128.9(4) . . . . ? Ta1 O2 C3 C6 131.2(4) . . . . ? Ta1 O2 C3 C5 -108.1(4) . . . . ? Ta1 O2 C3 C2 12.4(5) . . . . ? C1 C2 C3 O2 -51.8(4) . . . . ? C1 C2 C3 C6 -168.0(3) . . . . ? C1 C2 C3 C5 65.9(4) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.764 _refine_diff_density_min -1.203 _refine_diff_density_rms 0.154 # Attachment 'TaF_acac_3TaF6.cif' data_r-3 _database_code_depnum_ccdc_archive 'CCDC 649832' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H27 F7 O6 Ta2' _chemical_formula_weight 834.30 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' 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' Ta Ta -0.7052 6.5227 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 11.3387(15) _cell_length_b 11.3387(15) _cell_length_c 32.002(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3563.2(11) _cell_formula_units_Z 6 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5290 _cell_measurement_theta_min 2.4335 _cell_measurement_theta_max 28.2445 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2352 _exptl_absorpt_coefficient_mu 9.292 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2856 _exptl_absorpt_correction_T_max 0.4018 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12926 _diffrn_reflns_av_R_equivalents 0.0718 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.99 _reflns_number_total 1887 _reflns_number_gt 1535 _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^)+(0.0533P)^2^+13.5225P] 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 1887 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0455 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0931 _refine_ls_wR_factor_gt 0.0855 _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 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 Ta1 Ta 0.3333 0.6667 0.035149(10) 0.01503(13) Uani 1 3 d S . . F1 F 0.3333 0.6667 -0.02449(15) 0.0178(10) Uani 1 3 d S . . C1 C 0.3321(5) 1.0425(6) 0.02250(18) 0.0228(11) Uani 1 1 d . . . H1A H 0.3251 1.0274 -0.0078 0.034 Uiso 1 1 calc R . . H1B H 0.3963 1.1387 0.0283 0.034 Uiso 1 1 calc R . . H1C H 0.2424 1.0179 0.0338 0.034 Uiso 1 1 calc R . . C2 C 0.3817(5) 0.9565(5) 0.04243(16) 0.0168(10) Uani 1 1 d . . . C3 C 0.4519(5) 0.9897(5) 0.08061(16) 0.0188(11) Uani 1 1 d . . . C4 C 0.5042(5) 0.9083(5) 0.09466(16) 0.0159(10) Uani 1 1 d . . . C5 C 0.6045(6) 0.9507(6) 0.13009(18) 0.0245(12) Uani 1 1 d . . . H5A H 0.5561 0.9338 0.1567 0.037 Uiso 1 1 calc R . . H5B H 0.6713 1.0479 0.1276 0.037 Uiso 1 1 calc R . . H5C H 0.6515 0.8979 0.1290 0.037 Uiso 1 1 calc R . . C6 C 0.4767(6) 1.1160(5) 0.10390(18) 0.0244(12) Uani 1 1 d . . . H6A H 0.5202 1.1206 0.1308 0.037 Uiso 1 1 calc R . . H6B H 0.3896 1.1125 0.1087 0.037 Uiso 1 1 calc R . . H6C H 0.5363 1.1969 0.0873 0.037 Uiso 1 1 calc R . . O1 O 0.3554(4) 0.8487(4) 0.02067(11) 0.0167(7) Uani 1 1 d . . . O2 O 0.4755(4) 0.7934(4) 0.07799(11) 0.0187(8) Uani 1 1 d . . . Ta2 Ta 0.0000 1.0000 0.102974(11) 0.01805(14) Uani 1 3 d S . . F2 F 0.0175(4) 0.8724(3) 0.06901(11) 0.0304(8) Uani 1 1 d . . . F3 F 0.1444(3) 1.0163(4) 0.13681(11) 0.0312(8) 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 Ta1 0.01815(16) 0.01815(16) 0.0088(2) 0.000 0.000 0.00907(8) F1 0.0256(16) 0.0256(16) 0.002(2) 0.000 0.000 0.0128(8) C1 0.025(3) 0.026(3) 0.022(3) 0.005(2) 0.006(2) 0.016(2) C2 0.016(2) 0.021(2) 0.014(3) 0.0034(19) 0.0064(19) 0.009(2) C3 0.022(3) 0.019(2) 0.011(3) -0.002(2) 0.003(2) 0.007(2) C4 0.017(2) 0.017(2) 0.011(2) -0.0008(19) 0.0048(19) 0.007(2) C5 0.027(3) 0.029(3) 0.020(3) -0.003(2) -0.003(2) 0.016(2) C6 0.036(3) 0.020(3) 0.016(3) -0.003(2) -0.001(2) 0.013(2) O1 0.0228(18) 0.0167(17) 0.0108(18) 0.0020(13) 0.0003(14) 0.0100(15) O2 0.0226(18) 0.0169(18) 0.0149(19) -0.0020(14) -0.0018(15) 0.0087(15) Ta2 0.02152(16) 0.02152(16) 0.0111(2) 0.000 0.000 0.01076(8) F2 0.038(2) 0.0323(18) 0.0230(19) -0.0048(14) 0.0017(15) 0.0194(16) F3 0.0301(18) 0.040(2) 0.025(2) 0.0034(15) -0.0051(15) 0.0186(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 Ta1 F1 1.909(5) . ? Ta1 O1 2.005(3) . ? Ta1 O1 2.005(3) 2_665 ? Ta1 O1 2.005(3) 3_565 ? Ta1 O2 2.056(4) 2_665 ? Ta1 O2 2.056(4) . ? Ta1 O2 2.056(4) 3_565 ? C1 C2 1.490(7) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.305(6) . ? C2 C3 1.403(7) . ? C3 C4 1.398(7) . ? C3 C6 1.511(7) . ? C4 O2 1.290(6) . ? C4 C5 1.504(7) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? Ta2 F3 1.893(3) . ? Ta2 F3 1.893(3) 2_675 ? Ta2 F3 1.893(3) 3_465 ? Ta2 F2 1.897(3) 3_465 ? Ta2 F2 1.897(3) . ? Ta2 F2 1.897(3) 2_675 ? 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 F1 Ta1 O1 76.64(10) . . ? F1 Ta1 O1 76.64(10) . 2_665 ? O1 Ta1 O1 114.83(8) . 2_665 ? F1 Ta1 O1 76.64(10) . 3_565 ? O1 Ta1 O1 114.83(8) . 3_565 ? O1 Ta1 O1 114.83(8) 2_665 3_565 ? F1 Ta1 O2 131.82(10) . 2_665 ? O1 Ta1 O2 78.41(14) . 2_665 ? O1 Ta1 O2 77.53(14) 2_665 2_665 ? O1 Ta1 O2 151.53(15) 3_565 2_665 ? F1 Ta1 O2 131.82(10) . . ? O1 Ta1 O2 77.53(14) . . ? O1 Ta1 O2 151.53(15) 2_665 . ? O1 Ta1 O2 78.41(14) 3_565 . ? O2 Ta1 O2 80.39(15) 2_665 . ? F1 Ta1 O2 131.82(10) . 3_565 ? O1 Ta1 O2 151.53(15) . 3_565 ? O1 Ta1 O2 78.41(14) 2_665 3_565 ? O1 Ta1 O2 77.53(14) 3_565 3_565 ? O2 Ta1 O2 80.39(15) 2_665 3_565 ? O2 Ta1 O2 80.39(15) . 3_565 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 123.3(5) . . ? O1 C2 C1 113.6(4) . . ? C3 C2 C1 123.1(5) . . ? C4 C3 C2 118.3(5) . . ? C4 C3 C6 121.9(5) . . ? C2 C3 C6 119.7(5) . . ? O2 C4 C3 123.9(5) . . ? O2 C4 C5 113.7(4) . . ? C3 C4 C5 122.3(5) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C2 O1 Ta1 133.9(3) . . ? C4 O2 Ta1 134.0(3) . . ? F3 Ta2 F3 90.53(15) . 2_675 ? F3 Ta2 F3 90.53(15) . 3_465 ? F3 Ta2 F3 90.53(15) 2_675 3_465 ? F3 Ta2 F2 179.63(15) . 3_465 ? F3 Ta2 F2 89.77(15) 2_675 3_465 ? F3 Ta2 F2 89.25(15) 3_465 3_465 ? F3 Ta2 F2 89.25(15) . . ? F3 Ta2 F2 179.63(16) 2_675 . ? F3 Ta2 F2 89.77(15) 3_465 . ? F2 Ta2 F2 90.45(15) 3_465 . ? F3 Ta2 F2 89.77(15) . 2_675 ? F3 Ta2 F2 89.25(15) 2_675 2_675 ? F3 Ta2 F2 179.63(15) 3_465 2_675 ? F2 Ta2 F2 90.45(15) 3_465 2_675 ? F2 Ta2 F2 90.45(15) . 2_675 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 4.4(7) . . . . ? C1 C2 C3 C4 -174.5(5) . . . . ? O1 C2 C3 C6 -179.4(5) . . . . ? C1 C2 C3 C6 1.7(7) . . . . ? C2 C3 C4 O2 -10.5(7) . . . . ? C6 C3 C4 O2 173.4(5) . . . . ? C2 C3 C4 C5 167.1(5) . . . . ? C6 C3 C4 C5 -9.0(8) . . . . ? C3 C2 O1 Ta1 25.5(7) . . . . ? C1 C2 O1 Ta1 -155.5(4) . . . . ? F1 Ta1 O1 C2 -171.6(4) . . . . ? O1 Ta1 O1 C2 120.2(5) 2_665 . . . ? O1 Ta1 O1 C2 -103.4(5) 3_565 . . . ? O2 Ta1 O1 C2 49.9(4) 2_665 . . . ? O2 Ta1 O1 C2 -32.6(4) . . . . ? O2 Ta1 O1 C2 7.3(6) 3_565 . . . ? C3 C4 O2 Ta1 -11.6(8) . . . . ? C5 C4 O2 Ta1 170.6(3) . . . . ? F1 Ta1 O2 C4 84.7(5) . . . . ? O1 Ta1 O2 C4 25.7(4) . . . . ? O1 Ta1 O2 C4 -93.9(5) 2_665 . . . ? O1 Ta1 O2 C4 144.7(5) 3_565 . . . ? O2 Ta1 O2 C4 -54.5(5) 2_665 . . . ? O2 Ta1 O2 C4 -136.2(4) 3_565 . . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 27.99 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 1.907 _refine_diff_density_min -2.345 _refine_diff_density_rms 0.234 # Attachment 'Compound_4b.CIF' data_p21c _database_code_depnum_ccdc_archive 'CCDC 649833' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 Cl6 O2 Ta' _chemical_formula_weight 634.95 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.9858(11) _cell_length_b 11.0670(14) _cell_length_c 11.0162(14) _cell_angle_alpha 90.00 _cell_angle_beta 91.807(2) _cell_angle_gamma 90.00 _cell_volume 1095.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5679 _cell_measurement_theta_min 2.6095 _cell_measurement_theta_max 28.362 _exptl_crystal_description plate _exptl_crystal_colour pale-yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.926 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 5.759 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.3922 _exptl_absorpt_correction_T_max 0.5449 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11768 _diffrn_reflns_av_R_equivalents 0.0318 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 27.98 _reflns_number_total 2579 _reflns_number_gt 1995 _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^)+(0.0260P)^2^+1.6655P] 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 2579 _refine_ls_number_parameters 116 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0241 _refine_ls_wR_factor_ref 0.0633 _refine_ls_wR_factor_gt 0.0539 _refine_ls_goodness_of_fit_ref 1.155 _refine_ls_restrained_S_all 1.155 _refine_ls_shift/su_max 0.000 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1850(5) 0.6392(4) 0.6263(4) 0.0280(10) Uani 1 1 d . . . H1A H 0.0823 0.6219 0.6482 0.042 Uiso 1 1 calc R . . H1B H 0.1993 0.7268 0.6209 0.042 Uiso 1 1 calc R . . H1C H 0.2539 0.6059 0.6885 0.042 Uiso 1 1 calc R . . C2 C 0.2149(5) 0.5826(4) 0.5065(4) 0.0233(9) Uani 1 1 d . . . C3 C 0.3522(5) 0.6079(4) 0.4431(4) 0.0229(9) Uani 1 1 d . . . C4 C 0.4616(5) 0.6838(4) 0.4950(5) 0.0323(11) Uani 1 1 d . . . H4 H 0.4480 0.7185 0.5727 0.039 Uiso 1 1 calc R . . C5 C 0.5900(6) 0.7084(5) 0.4325(6) 0.0413(13) Uani 1 1 d . . . H5 H 0.6643 0.7599 0.4673 0.050 Uiso 1 1 calc R . . C6 C 0.6093(5) 0.6574(5) 0.3194(5) 0.0386(12) Uani 1 1 d . . . H6 H 0.6971 0.6744 0.2768 0.046 Uiso 1 1 calc R . . C7 C 0.5027(5) 0.5822(5) 0.2677(4) 0.0358(12) Uani 1 1 d . . . H7 H 0.5175 0.5474 0.1902 0.043 Uiso 1 1 calc R . . C8 C 0.3731(5) 0.5572(5) 0.3293(4) 0.0301(10) Uani 1 1 d . . . H8 H 0.2992 0.5057 0.2937 0.036 Uiso 1 1 calc R . . Cl1 Cl 0.98934(12) 0.59183(10) 0.19030(9) 0.0252(2) Uani 1 1 d . . . Cl2 Cl 0.73953(12) 0.47327(9) -0.00214(10) 0.0267(2) Uani 1 1 d . . . Cl3 Cl 1.02968(12) 0.31079(9) 0.09381(10) 0.0259(2) Uani 1 1 d . . . O1 O 0.1227(3) 0.5128(3) 0.4570(3) 0.0276(7) Uani 1 1 d . . . H1 H 0.0000 0.5000 0.5000 0.041 Uiso 1 2 d S . . Ta1 Ta 1.0000 0.5000 0.0000 0.01702(8) Uani 1 2 d S . . 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 0.030(2) 0.026(2) 0.028(2) 0.0004(19) 0.0091(19) 0.0003(18) C2 0.023(2) 0.022(2) 0.026(2) 0.0076(18) 0.0033(17) 0.0023(17) C3 0.021(2) 0.021(2) 0.027(2) 0.0052(18) 0.0054(17) 0.0042(17) C4 0.026(3) 0.026(2) 0.045(3) -0.002(2) 0.010(2) -0.0006(17) C5 0.027(3) 0.030(3) 0.067(4) 0.002(3) 0.010(2) -0.005(2) C6 0.022(2) 0.041(3) 0.053(3) 0.013(3) 0.015(2) 0.002(2) C7 0.028(2) 0.052(3) 0.028(3) 0.008(2) 0.0084(19) 0.008(2) C8 0.022(2) 0.041(3) 0.027(2) 0.004(2) 0.0026(18) 0.002(2) Cl1 0.0324(6) 0.0236(5) 0.0201(5) -0.0039(4) 0.0071(4) -0.0026(4) Cl2 0.0231(5) 0.0282(6) 0.0290(5) -0.0024(4) 0.0057(4) -0.0017(4) Cl3 0.0334(6) 0.0191(5) 0.0256(5) 0.0046(4) 0.0056(4) 0.0023(4) O1 0.0229(15) 0.0324(18) 0.0278(15) 0.0029(14) 0.0048(12) -0.0026(14) Ta1 0.02064(12) 0.01504(11) 0.01568(11) 0.00025(10) 0.00525(7) 0.00004(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.493(6) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 O1 1.246(5) . ? C2 C3 1.464(6) . ? C3 C8 1.392(6) . ? C3 C4 1.402(6) . ? C4 C5 1.389(6) . ? C4 H4 0.9500 . ? C5 C6 1.383(8) . ? C5 H5 0.9500 . ? C6 C7 1.378(7) . ? C6 H6 0.9500 . ? C7 C8 1.394(6) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? Cl1 Ta1 2.3344(10) . ? Cl2 Ta1 2.3586(11) . ? Cl3 Ta1 2.3466(10) . ? O1 H1 1.221(3) . ? Ta1 Cl1 2.3344(10) 3_765 ? Ta1 Cl3 2.3466(10) 3_765 ? Ta1 Cl2 2.3586(11) 3_765 ? 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 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 118.0(4) . . ? O1 C2 C1 120.7(4) . . ? C3 C2 C1 121.3(4) . . ? C8 C3 C4 119.8(4) . . ? C8 C3 C2 119.5(4) . . ? C4 C3 C2 120.8(4) . . ? C5 C4 C3 119.9(5) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C6 C5 C4 119.7(5) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C6 C5 120.9(5) . . ? C7 C6 H6 119.6 . . ? C5 C6 H6 119.6 . . ? C6 C7 C8 120.0(5) . . ? C6 C7 H7 120.0 . . ? C8 C7 H7 120.0 . . ? C3 C8 C7 119.8(5) . . ? C3 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C2 O1 H1 119.9(3) . . ? Cl1 Ta1 Cl1 180 3_765 . ? Cl1 Ta1 Cl3 90.02(4) 3_765 3_765 ? Cl1 Ta1 Cl3 89.98(4) . 3_765 ? Cl1 Ta1 Cl3 89.98(4) 3_765 . ? Cl1 Ta1 Cl3 90.02(4) . . ? Cl3 Ta1 Cl3 180 3_765 . ? Cl1 Ta1 Cl2 90.30(4) 3_765 . ? Cl1 Ta1 Cl2 89.70(4) . . ? Cl3 Ta1 Cl2 90.49(4) 3_765 . ? Cl3 Ta1 Cl2 89.51(4) . . ? Cl1 Ta1 Cl2 89.70(4) 3_765 3_765 ? Cl1 Ta1 Cl2 90.30(4) . 3_765 ? Cl3 Ta1 Cl2 89.51(4) 3_765 3_765 ? Cl3 Ta1 Cl2 90.49(4) . 3_765 ? Cl2 Ta1 Cl2 180 . 3_765 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C8 2.2(6) . . . . ? C1 C2 C3 C8 -177.4(4) . . . . ? O1 C2 C3 C4 -178.8(4) . . . . ? C1 C2 C3 C4 1.6(6) . . . . ? C8 C3 C4 C5 0.1(7) . . . . ? C2 C3 C4 C5 -178.9(4) . . . . ? C3 C4 C5 C6 -0.1(8) . . . . ? C4 C5 C6 C7 -0.1(8) . . . . ? C5 C6 C7 C8 0.3(8) . . . . ? C4 C3 C8 C7 0.1(7) . . . . ? C2 C3 C8 C7 179.1(4) . . . . ? C6 C7 C8 C3 -0.3(7) . . . . ? 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 O1 H1 O1 1.22 1.22 2.443(6) 180 3_566 _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 27.98 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 1.736 _refine_diff_density_min -0.886 _refine_diff_density_rms 0.141 # Attachment 'Compound_4a.CIF' data_c2c _database_code_depnum_ccdc_archive 'CCDC 649834' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H21 F6 O2 Ta' _chemical_formula_weight 660.38 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' 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' Ta Ta -0.7052 6.5227 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 14.504(3) _cell_length_b 9.6665(18) _cell_length_c 17.500(5) _cell_angle_alpha 90.00 _cell_angle_beta 107.741(2) _cell_angle_gamma 90.00 _cell_volume 2336.8(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5407 _cell_measurement_theta_min 2.444 _cell_measurement_theta_max 28.4795 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.877 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 4.773 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4198 _exptl_absorpt_correction_T_max 0.5346 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11565 _diffrn_reflns_av_R_equivalents 0.0317 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.44 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2383 _reflns_number_gt 2329 _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^)+(0.0248P)^2^+1.8168P] 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 2383 _refine_ls_number_parameters 159 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0172 _refine_ls_R_factor_gt 0.0168 _refine_ls_wR_factor_ref 0.0443 _refine_ls_wR_factor_gt 0.0439 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.002 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.34803(16) 0.5015(2) 0.93567(12) 0.0272(4) Uani 1 1 d . . . C2 C 0.34956(17) 0.3553(2) 0.91398(14) 0.0254(4) Uani 1 1 d . . . C3 C 0.39270(18) 0.2579(3) 0.97356(15) 0.0338(5) Uani 1 1 d . . . H3 H 0.4212 0.2863 1.0276 0.041 Uiso 1 1 calc R . . C4 C 0.3933(2) 0.1197(3) 0.95273(18) 0.0412(6) Uani 1 1 d . . . H4 H 0.4202 0.0527 0.9931 0.049 Uiso 1 1 calc R . . C5 C 0.35509(18) 0.0786(2) 0.87416(17) 0.0363(6) Uani 1 1 d . . . H5 H 0.3577 -0.0160 0.8604 0.044 Uiso 1 1 calc R . . C6 C 0.3130(2) 0.1740(2) 0.81515(17) 0.0318(6) Uani 1 1 d . . . H6 H 0.2868 0.1448 0.7610 0.038 Uiso 1 1 calc R . . C7 C 0.30886(18) 0.3117(2) 0.83465(15) 0.0257(5) Uani 1 1 d . . . H7 H 0.2784 0.3768 0.7942 0.031 Uiso 1 1 calc R . . C8 C 0.26048(16) 0.5854(2) 0.90554(13) 0.0250(4) Uani 1 1 d . . . C9 C 0.26745(18) 0.7302(2) 0.90855(14) 0.0301(5) Uani 1 1 d . . . H9 H 0.3290 0.7732 0.9287 0.036 Uiso 1 1 calc R . . C10 C 0.1847(2) 0.8105(3) 0.88217(16) 0.0309(5) Uani 1 1 d . . . H10 H 0.1895 0.9085 0.8833 0.037 Uiso 1 1 calc R . . C11 C 0.09482(17) 0.7473(3) 0.85402(14) 0.0306(5) Uani 1 1 d . . . H11 H 0.0381 0.8026 0.8366 0.037 Uiso 1 1 calc R . . C12 C 0.08697(17) 0.6035(3) 0.85103(14) 0.0300(5) Uani 1 1 d . . . H12 H 0.0251 0.5612 0.8314 0.036 Uiso 1 1 calc R . . C13 C 0.16925(16) 0.5224(2) 0.87666(13) 0.0266(4) Uani 1 1 d . . . H13 H 0.1640 0.4245 0.8747 0.032 Uiso 1 1 calc R . . F1 F 0.39516(13) 0.66904(17) 0.65443(11) 0.0486(5) Uani 1 1 d . . . F2 F 0.43770(12) 0.53429(18) 0.79344(11) 0.0470(4) Uani 1 1 d . . . F3 F 0.43854(16) 0.80945(18) 0.79310(14) 0.0552(5) Uani 1 1 d . . . O1 O 0.42152(12) 0.55883(18) 0.98270(11) 0.0369(4) Uani 1 1 d . . . H1 H 0.5000 0.5000 1.0000 0.044 Uiso 1 2 d S . . Ta1 Ta 0.5000 0.670741(11) 0.7500 0.02402(6) Uani 1 2 d S . . 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 0.0284(11) 0.0290(11) 0.0237(10) -0.0019(9) 0.0070(8) 0.0009(9) C2 0.0256(11) 0.0251(10) 0.0266(11) 0.0007(9) 0.0095(9) 0.0040(9) C3 0.0369(13) 0.0370(13) 0.0287(11) 0.0056(10) 0.0117(10) 0.0103(10) C4 0.0458(15) 0.0318(14) 0.0541(16) 0.0191(12) 0.0274(13) 0.0150(12) C5 0.0390(13) 0.0201(11) 0.0598(16) 0.0001(10) 0.0299(12) 0.0007(9) C6 0.0330(13) 0.0280(13) 0.0395(14) -0.0076(8) 0.0186(11) -0.0062(8) C7 0.0262(11) 0.0249(10) 0.0273(11) 0.0009(8) 0.0100(9) -0.0005(8) C8 0.0263(11) 0.0243(11) 0.0243(10) -0.0006(8) 0.0075(8) 0.0020(9) C9 0.0310(12) 0.0250(12) 0.0327(11) -0.0047(9) 0.0075(10) -0.0011(9) C10 0.0373(14) 0.0228(10) 0.0339(13) 0.0000(9) 0.0125(11) 0.0050(9) C11 0.0304(12) 0.0314(12) 0.0313(11) 0.0031(9) 0.0113(10) 0.0081(10) C12 0.0260(11) 0.0316(12) 0.0334(11) 0.0019(9) 0.0103(9) 0.0004(9) C13 0.0299(11) 0.0232(10) 0.0280(10) 0.0008(8) 0.0110(9) -0.0018(9) F1 0.0351(9) 0.0727(14) 0.0356(9) 0.0086(7) 0.0069(7) 0.0058(7) F2 0.0479(9) 0.0401(9) 0.0579(10) 0.0150(8) 0.0235(8) -0.0085(7) F3 0.0606(12) 0.0388(9) 0.0785(14) -0.0167(9) 0.0394(11) 0.0066(8) O1 0.0283(9) 0.0346(9) 0.0395(9) -0.0145(7) -0.0019(7) 0.0063(7) Ta1 0.02734(9) 0.01811(8) 0.02922(8) 0.000 0.01251(6) 0.000 _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 O1 1.259(3) . ? C1 C8 1.463(3) . ? C1 C2 1.465(3) . ? C2 C7 1.398(3) . ? C2 C3 1.403(3) . ? C3 C4 1.385(4) . ? C3 H3 0.9500 . ? C4 C5 1.375(4) . ? C4 H4 0.9500 . ? C5 C6 1.380(4) . ? C5 H5 0.9500 . ? C6 C7 1.380(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.403(3) . ? C8 C13 1.403(3) . ? C9 C10 1.385(4) . ? C9 H9 0.9500 . ? C10 C11 1.387(4) . ? C10 H10 0.9500 . ? C11 C12 1.395(4) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? F1 Ta1 1.8867(18) . ? F2 Ta1 1.8849(15) . ? F3 Ta1 1.8897(17) . ? O1 H1 1.2250(17) . ? Ta1 F2 1.8849(15) 2_656 ? Ta1 F1 1.8867(18) 2_656 ? Ta1 F3 1.8897(17) 2_656 ? 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 O1 C1 C8 117.4(2) . . ? O1 C1 C2 121.2(2) . . ? C8 C1 C2 121.4(2) . . ? C7 C2 C3 119.6(2) . . ? C7 C2 C1 120.8(2) . . ? C3 C2 C1 119.6(2) . . ? C4 C3 C2 119.3(2) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C5 C4 C3 120.6(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 120.5(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C7 120.1(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 120.0(2) . . ? C6 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? C9 C8 C13 119.71(19) . . ? C9 C8 C1 119.67(19) . . ? C13 C8 C1 120.6(2) . . ? C10 C9 C8 120.1(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 119.8(2) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C10 C11 C12 120.6(2) . . ? C10 C11 H11 119.7 . . ? C12 C11 H11 119.7 . . ? C13 C12 C11 120.0(2) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 119.8(2) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? C1 O1 H1 119.65(17) . . ? F2 Ta1 F2 91.18(11) 2_656 . ? F2 Ta1 F1 89.56(8) 2_656 . ? F2 Ta1 F1 89.74(8) . . ? F2 Ta1 F1 89.74(8) 2_656 2_656 ? F2 Ta1 F1 89.56(8) . 2_656 ? F1 Ta1 F1 179.00(10) . 2_656 ? F2 Ta1 F3 89.61(10) 2_656 2_656 ? F2 Ta1 F3 179.21(7) . 2_656 ? F1 Ta1 F3 90.18(9) . 2_656 ? F1 Ta1 F3 90.52(9) 2_656 2_656 ? F2 Ta1 F3 179.21(7) 2_656 . ? F2 Ta1 F3 89.61(10) . . ? F1 Ta1 F3 90.52(9) . . ? F1 Ta1 F3 90.18(9) 2_656 . ? F3 Ta1 F3 89.60(13) 2_656 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C7 -136.6(2) . . . . ? C8 C1 C2 C7 45.3(3) . . . . ? O1 C1 C2 C3 43.2(3) . . . . ? C8 C1 C2 C3 -135.0(2) . . . . ? C7 C2 C3 C4 -0.7(4) . . . . ? C1 C2 C3 C4 179.5(2) . . . . ? C2 C3 C4 C5 2.3(4) . . . . ? C3 C4 C5 C6 -2.0(4) . . . . ? C4 C5 C6 C7 0.0(4) . . . . ? C5 C6 C7 C2 1.6(4) . . . . ? C3 C2 C7 C6 -1.2(4) . . . . ? C1 C2 C7 C6 178.5(2) . . . . ? O1 C1 C8 C9 19.3(3) . . . . ? C2 C1 C8 C9 -162.5(2) . . . . ? O1 C1 C8 C13 -158.2(2) . . . . ? C2 C1 C8 C13 20.1(3) . . . . ? C13 C8 C9 C10 -0.8(3) . . . . ? C1 C8 C9 C10 -178.3(2) . . . . ? C8 C9 C10 C11 1.1(4) . . . . ? C9 C10 C11 C12 -0.8(4) . . . . ? C10 C11 C12 C13 0.3(3) . . . . ? C11 C12 C13 C8 -0.1(3) . . . . ? C9 C8 C13 C12 0.3(3) . . . . ? C1 C8 C13 C12 177.7(2) . . . . ? 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 O1 H1 O1 1.23 1.23 2.450(3) 180 5_667 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.398 _refine_diff_density_min -0.360 _refine_diff_density_rms 0.079 # Attachment 'tacl5ph2co.CIF' data_c2c_tacl _database_code_depnum_ccdc_archive 'CCDC 649835' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 Cl5 O Ta' _chemical_formula_weight 540.41 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c 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 29.442(3) _cell_length_b 8.8967(10) _cell_length_c 12.8833(14) _cell_angle_alpha 90.00 _cell_angle_beta 103.032(2) _cell_angle_gamma 90.00 _cell_volume 3287.6(6) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6384 _cell_measurement_theta_min 2.385 _cell_measurement_theta_max 28.626 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.184 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2032 _exptl_absorpt_coefficient_mu 7.489 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.2896 _exptl_absorpt_correction_T_max 0.4203 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17756 _diffrn_reflns_av_R_equivalents 0.0269 _diffrn_reflns_av_sigmaI/netI 0.0195 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 37 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.42 _diffrn_reflns_theta_max 27.09 _reflns_number_total 3633 _reflns_number_gt 3517 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0113P)^2^+7.3159P] 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 3633 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0181 _refine_ls_R_factor_gt 0.0172 _refine_ls_wR_factor_ref 0.0392 _refine_ls_wR_factor_gt 0.0388 _refine_ls_goodness_of_fit_ref 1.179 _refine_ls_restrained_S_all 1.179 _refine_ls_shift/su_max 0.004 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ta1 Ta 0.376291(3) 1.181576(11) 0.722427(8) 0.01338(4) Uani 1 1 d . . . Cl1 Cl 0.39647(2) 1.25715(7) 0.56461(5) 0.02390(14) Uani 1 1 d . . . Cl2 Cl 0.45409(2) 1.20008(8) 0.81307(6) 0.02552(15) Uani 1 1 d . . . Cl3 Cl 0.36312(2) 1.42136(7) 0.77694(5) 0.01961(13) Uani 1 1 d . . . Cl4 Cl 0.35851(2) 1.06691(7) 0.87245(5) 0.01971(13) Uani 1 1 d . . . Cl5 Cl 0.29830(2) 1.16645(8) 0.62973(5) 0.02332(14) Uani 1 1 d . . . O1 O 0.38645(6) 0.9707(2) 0.67619(15) 0.0185(4) Uani 1 1 d . . . C1 C 0.38747(9) 0.8398(3) 0.6386(2) 0.0150(5) Uani 1 1 d . . . C2 C 0.43176(9) 0.7830(3) 0.62192(19) 0.0150(5) Uani 1 1 d . . . C3 C 0.44107(9) 0.6284(3) 0.6245(2) 0.0173(5) Uani 1 1 d . . . H3 H 0.4178 0.5589 0.6337 0.021 Uiso 1 1 calc R . . C4 C 0.48384(9) 0.5768(3) 0.6138(2) 0.0215(6) Uani 1 1 d . . . H4 H 0.4901 0.4720 0.6160 0.026 Uiso 1 1 calc R . . C5 C 0.51804(10) 0.6782(3) 0.5997(2) 0.0222(6) Uani 1 1 d . . . H5 H 0.5475 0.6422 0.5919 0.027 Uiso 1 1 calc R . . C6 C 0.50928(10) 0.8315(3) 0.5971(2) 0.0220(6) Uani 1 1 d . . . H6 H 0.5326 0.9000 0.5869 0.026 Uiso 1 1 calc R . . C7 C 0.46669(9) 0.8851(3) 0.6095(2) 0.0190(5) Uani 1 1 d . . . H7 H 0.4611 0.9902 0.6095 0.023 Uiso 1 1 calc R . . C8 C 0.34477(9) 0.7503(3) 0.6167(2) 0.0144(5) Uani 1 1 d . . . C9 C 0.33691(9) 0.6412(3) 0.5361(2) 0.0168(5) Uani 1 1 d . . . H9 H 0.3593 0.6254 0.4944 0.020 Uiso 1 1 calc R . . C10 C 0.29673(9) 0.5569(3) 0.5173(2) 0.0199(5) Uani 1 1 d . . . H10 H 0.2913 0.4837 0.4622 0.024 Uiso 1 1 calc R . . C11 C 0.26407(9) 0.5784(3) 0.5786(2) 0.0214(6) Uani 1 1 d . . . H11 H 0.2367 0.5183 0.5663 0.026 Uiso 1 1 calc R . . C12 C 0.27119(10) 0.6871(3) 0.6578(2) 0.0219(6) Uani 1 1 d . . . H12 H 0.2486 0.7018 0.6991 0.026 Uiso 1 1 calc R . . C13 C 0.31110(9) 0.7742(3) 0.6766(2) 0.0182(5) Uani 1 1 d . . . H13 H 0.3157 0.8499 0.7300 0.022 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 0.01695(6) 0.00776(6) 0.01638(6) -0.00186(4) 0.00574(4) -0.00110(4) Cl1 0.0373(4) 0.0152(3) 0.0242(3) -0.0018(2) 0.0173(3) -0.0036(3) Cl2 0.0189(3) 0.0184(3) 0.0374(4) -0.0016(3) 0.0024(3) -0.0017(2) Cl3 0.0320(3) 0.0092(3) 0.0188(3) -0.0008(2) 0.0083(2) 0.0031(2) Cl4 0.0282(3) 0.0136(3) 0.0183(3) 0.0000(2) 0.0073(2) -0.0027(2) Cl5 0.0213(3) 0.0244(3) 0.0229(3) -0.0011(3) 0.0021(2) -0.0029(3) O1 0.0244(9) 0.0088(9) 0.0257(10) -0.0045(7) 0.0126(8) -0.0026(7) C1 0.0212(13) 0.0106(12) 0.0136(12) 0.0008(9) 0.0047(10) -0.0003(9) C2 0.0182(12) 0.0125(12) 0.0145(12) -0.0015(10) 0.0043(9) 0.0001(10) C3 0.0214(13) 0.0121(12) 0.0179(12) -0.0012(10) 0.0036(10) -0.0011(10) C4 0.0264(14) 0.0154(13) 0.0227(13) 0.0005(11) 0.0056(11) 0.0035(11) C5 0.0191(13) 0.0274(16) 0.0204(13) -0.0004(11) 0.0052(10) 0.0057(11) C6 0.0208(13) 0.0233(15) 0.0229(14) -0.0032(11) 0.0071(11) -0.0061(11) C7 0.0240(13) 0.0139(13) 0.0197(13) -0.0044(10) 0.0060(10) -0.0045(10) C8 0.0186(12) 0.0081(11) 0.0165(12) 0.0031(9) 0.0040(9) -0.0006(9) C9 0.0211(13) 0.0135(12) 0.0160(12) 0.0022(10) 0.0044(10) 0.0015(10) C10 0.0229(13) 0.0147(13) 0.0201(13) -0.0020(10) 0.0005(10) -0.0029(10) C11 0.0193(12) 0.0174(13) 0.0257(14) 0.0041(11) 0.0008(10) -0.0034(10) C12 0.0208(13) 0.0197(14) 0.0277(15) 0.0021(11) 0.0108(11) -0.0001(10) C13 0.0234(13) 0.0129(12) 0.0195(13) -0.0003(10) 0.0077(10) 0.0007(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Ta1 O1 2.0108(18) . ? Ta1 Cl3 2.3059(6) . ? Ta1 Cl2 2.3304(7) . ? Ta1 Cl5 2.3408(7) . ? Ta1 Cl1 2.3417(7) . ? Ta1 Cl4 2.3466(7) . ? O1 C1 1.265(3) . ? C1 C2 1.459(4) . ? C1 C8 1.461(3) . ? C2 C3 1.402(4) . ? C2 C7 1.408(4) . ? C3 C4 1.376(4) . ? C3 H3 0.9500 . ? C4 C5 1.394(4) . ? C4 H4 0.9500 . ? C5 C6 1.386(4) . ? C5 H5 0.9500 . ? C6 C7 1.384(4) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C8 C9 1.402(4) . ? C8 C13 1.404(4) . ? C9 C10 1.375(4) . ? C9 H9 0.9500 . ? C10 C11 1.388(4) . ? C10 H10 0.9500 . ? C11 C12 1.387(4) . ? C11 H11 0.9500 . ? C12 C13 1.382(4) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? 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 O1 Ta1 Cl3 178.62(5) . . ? O1 Ta1 Cl2 91.10(6) . . ? Cl3 Ta1 Cl2 89.76(2) . . ? O1 Ta1 Cl5 89.40(6) . . ? Cl3 Ta1 Cl5 89.75(2) . . ? Cl2 Ta1 Cl5 179.06(3) . . ? O1 Ta1 Cl1 85.80(5) . . ? Cl3 Ta1 Cl1 95.27(2) . . ? Cl2 Ta1 Cl1 90.09(3) . . ? Cl5 Ta1 Cl1 89.16(3) . . ? O1 Ta1 Cl4 85.08(6) . . ? Cl3 Ta1 Cl4 93.86(2) . . ? Cl2 Ta1 Cl4 89.69(3) . . ? Cl5 Ta1 Cl4 91.14(2) . . ? Cl1 Ta1 Cl4 170.87(2) . . ? C1 O1 Ta1 172.22(18) . . ? O1 C1 C2 118.3(2) . . ? O1 C1 C8 118.9(2) . . ? C2 C1 C8 122.8(2) . . ? C3 C2 C7 119.4(2) . . ? C3 C2 C1 120.8(2) . . ? C7 C2 C1 119.6(2) . . ? C4 C3 C2 120.2(2) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C5 120.3(3) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C2 119.7(3) . . ? C6 C7 H7 120.2 . . ? C2 C7 H7 120.2 . . ? C9 C8 C13 119.5(2) . . ? C9 C8 C1 120.8(2) . . ? C13 C8 C1 119.7(2) . . ? C10 C9 C8 120.0(2) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.3(2) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 120.3(2) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.1(3) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 119.8(3) . . ? C12 C13 H13 120.1 . . ? C8 C13 H13 120.1 . . ? 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 Cl3 Ta1 O1 C1 63(3) . . . . ? Cl2 Ta1 O1 C1 -168.1(13) . . . . ? Cl5 Ta1 O1 C1 11.1(13) . . . . ? Cl1 Ta1 O1 C1 -78.1(13) . . . . ? Cl4 Ta1 O1 C1 102.3(13) . . . . ? Ta1 O1 C1 C2 142.3(12) . . . . ? Ta1 O1 C1 C8 -39.5(14) . . . . ? O1 C1 C2 C3 153.0(2) . . . . ? C8 C1 C2 C3 -25.2(4) . . . . ? O1 C1 C2 C7 -23.2(4) . . . . ? C8 C1 C2 C7 158.6(2) . . . . ? C7 C2 C3 C4 -0.7(4) . . . . ? C1 C2 C3 C4 -176.8(2) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C3 C4 C5 C6 0.4(4) . . . . ? C4 C5 C6 C7 0.6(4) . . . . ? C5 C6 C7 C2 -1.6(4) . . . . ? C3 C2 C7 C6 1.7(4) . . . . ? C1 C2 C7 C6 177.9(2) . . . . ? O1 C1 C8 C9 151.3(2) . . . . ? C2 C1 C8 C9 -30.5(4) . . . . ? O1 C1 C8 C13 -28.4(4) . . . . ? C2 C1 C8 C13 149.8(2) . . . . ? C13 C8 C9 C10 -1.0(4) . . . . ? C1 C8 C9 C10 179.3(2) . . . . ? C8 C9 C10 C11 -0.6(4) . . . . ? C9 C10 C11 C12 1.4(4) . . . . ? C10 C11 C12 C13 -0.5(4) . . . . ? C11 C12 C13 C8 -1.1(4) . . . . ? C9 C8 C13 C12 1.8(4) . . . . ? C1 C8 C13 C12 -178.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.09 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.420 _refine_diff_density_min -1.065 _refine_diff_density_rms 0.101