# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Simon Lotz' _publ_contact_author_email SIMON.LOTZ@UP.AC.ZA _publ_section_title ; Synthesis and Reactivity of Metal Carbene Complexes with Heterobiaryl Spacer Substituents ; loop_ _publ_author_name 'Simon Lotz' 'Daniela I Bezuidenhout' 'Chantelle Crause' 'Helmar Gorls' 'Marile Landman' 'David C Liles' ; A.J.Olivier ; data_FO1045 _database_code_depnum_ccdc_archive 'CCDC 686736' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H20 N2 O12 W2' _chemical_formula_sum 'C26 H20 N2 O12 W2' _chemical_formula_weight 920.14 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' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pccn _symmetry_space_group_name_Hall -P2ab2ac loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y, -z+1/2' '-x, -y, -z' 'x-1/2, y-1/2, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y, z-1/2' _cell_length_a 17.7003(6) _cell_length_b 12.5957(4) _cell_length_c 13.4575(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3000.32(15) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 18869 _cell_measurement_theta_min 3.43 _cell_measurement_theta_max 27.49 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.037 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1736 _exptl_absorpt_coefficient_mu 7.725 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. R.H. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.625 _exptl_absorpt_correction_T_max 0.697 _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 KappaCCD _diffrn_measurement_method phi-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18869 _diffrn_reflns_av_R_equivalents 0.0563 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.43 _diffrn_reflns_theta_max 27.49 _reflns_number_total 3431 _reflns_number_gt 2779 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.0343P)^2^+0.5780P] 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 3431 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0313 _refine_ls_wR_factor_ref 0.0709 _refine_ls_wR_factor_gt 0.0663 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 W W 0.435193(9) 0.339562(12) 0.208198(12) 0.02706(8) Uani 1 1 d . . . O1 O 0.32127(17) 0.4856(2) 0.33533(19) 0.0323(6) Uani 1 1 d . . . N1 N 0.27595(19) 0.6298(3) 0.2028(2) 0.0263(7) Uani 1 1 d . . . C1 C 0.3558(2) 0.4700(3) 0.2499(3) 0.0246(8) Uani 1 1 d . . . C2 C 0.3326(2) 0.5554(3) 0.1829(3) 0.0238(8) Uani 1 1 d . . . C3 C 0.3663(2) 0.5853(3) 0.0936(3) 0.0292(9) Uani 1 1 d . . . H3A H 0.4061 0.5484 0.0612 0.035 Uiso 1 1 calc R . . C4 C 0.3319(2) 0.6791(3) 0.0591(3) 0.0313(9) Uani 1 1 d . . . H4A H 0.3444 0.7172 0.0004 0.038 Uiso 1 1 calc R . . C5 C 0.2759(2) 0.7053(3) 0.1279(3) 0.0269(8) Uani 1 1 d . . . C6 C 0.2160(3) 0.6232(4) 0.2775(3) 0.0395(11) Uani 1 1 d . . . H6A H 0.1846 0.6872 0.2741 0.059 Uiso 1 1 calc R . . H6B H 0.2386 0.6176 0.3437 0.059 Uiso 1 1 calc R . . H6C H 0.1848 0.5605 0.2646 0.059 Uiso 1 1 calc R . . C7 C 0.3271(3) 0.4153(4) 0.4204(3) 0.0462(12) Uani 1 1 d . . . H7A H 0.2808 0.3714 0.4252 0.055 Uiso 1 1 calc R . . H7B H 0.3707 0.3670 0.4113 0.055 Uiso 1 1 calc R . . C8 C 0.3365(5) 0.4741(5) 0.5096(4) 0.097(3) Uani 1 1 d . . . H8A H 0.3407 0.4251 0.5659 0.146 Uiso 1 1 calc R . . H8B H 0.2929 0.5208 0.5194 0.146 Uiso 1 1 calc R . . H8C H 0.3826 0.5170 0.5051 0.146 Uiso 1 1 calc R . . O2 O 0.5559(2) 0.5119(4) 0.1380(4) 0.0752(13) Uani 1 1 d . . . O3 O 0.5197(3) 0.3300(4) 0.4166(3) 0.0921(17) Uani 1 1 d . . . O4 O 0.5504(3) 0.1592(4) 0.1440(3) 0.0920(19) Uani 1 1 d . . . O5 O 0.3156(3) 0.1599(3) 0.2663(3) 0.0550(10) Uani 1 1 d . . . O6 O 0.3605(3) 0.3272(3) -0.0065(3) 0.0571(10) Uani 1 1 d . . . C9 C 0.5124(3) 0.4508(4) 0.1634(4) 0.0430(11) Uani 1 1 d . . . C10 C 0.4875(3) 0.3353(4) 0.3437(4) 0.0504(13) Uani 1 1 d . . . C11 C 0.5083(3) 0.2244(4) 0.1667(3) 0.0511(14) Uani 1 1 d . . . C12 C 0.3585(3) 0.2257(4) 0.2488(3) 0.0348(10) Uani 1 1 d . . . C13 C 0.3872(3) 0.3343(3) 0.0700(3) 0.0351(10) 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 W 0.03092(12) 0.02490(12) 0.02538(12) -0.00110(6) -0.00148(6) 0.00796(6) O1 0.0454(17) 0.0264(14) 0.0250(13) 0.0016(11) 0.0101(13) 0.0085(13) N1 0.0299(17) 0.0210(16) 0.0279(17) -0.0011(13) 0.0083(14) 0.0037(14) C1 0.0260(19) 0.022(2) 0.0255(19) -0.0024(15) 0.0010(16) -0.0007(16) C2 0.030(2) 0.0159(18) 0.0255(18) -0.0013(14) 0.0017(16) -0.0007(15) C3 0.035(2) 0.024(2) 0.028(2) -0.0001(16) 0.0078(17) 0.0074(17) C4 0.040(2) 0.030(2) 0.0236(19) 0.0030(15) 0.0048(18) 0.0041(18) C5 0.035(2) 0.0188(19) 0.0272(19) -0.0006(16) 0.0007(17) -0.0011(16) C6 0.043(3) 0.028(2) 0.048(3) 0.008(2) 0.019(2) 0.008(2) C7 0.077(4) 0.032(2) 0.029(2) 0.0103(19) 0.010(2) 0.014(2) C8 0.211(9) 0.052(4) 0.028(3) 0.001(2) -0.012(4) 0.009(5) O2 0.045(2) 0.093(3) 0.088(3) 0.024(3) 0.002(2) -0.022(2) O3 0.085(3) 0.145(5) 0.047(3) -0.008(2) -0.035(3) 0.030(3) O4 0.126(4) 0.102(4) 0.048(3) 0.001(2) 0.011(3) 0.088(3) O5 0.065(3) 0.035(2) 0.065(2) -0.0002(16) 0.001(2) -0.0095(18) O6 0.090(3) 0.043(2) 0.038(2) -0.0083(14) -0.021(2) -0.0012(18) C9 0.031(2) 0.056(3) 0.043(3) 0.008(2) -0.002(2) 0.001(2) C10 0.047(3) 0.062(4) 0.042(3) -0.009(2) -0.010(3) 0.013(2) C11 0.064(3) 0.064(3) 0.025(2) 0.007(2) -0.001(2) 0.033(3) C12 0.046(3) 0.028(2) 0.030(2) -0.0007(18) 0.000(2) 0.006(2) C13 0.051(3) 0.021(2) 0.033(2) -0.0065(16) -0.006(2) 0.0087(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 W C11 2.022(5) . ? W C13 2.045(5) . ? W C12 2.049(5) . ? W C10 2.046(5) . ? W C9 2.048(5) . ? W C1 2.234(4) . ? O1 C1 1.317(5) . ? O1 C7 1.451(5) . ? N1 C5 1.385(5) . ? N1 C2 1.398(5) . ? N1 C6 1.463(5) . ? C1 C2 1.462(5) . ? C2 C3 1.394(5) . ? C3 C4 1.409(5) . ? C4 C5 1.395(5) . ? C5 C5 1.453(8) 2_565 ? C7 C8 1.421(7) . ? O2 C9 1.141(6) . ? O3 C10 1.137(6) . ? O4 C11 1.151(6) . ? O5 C12 1.148(6) . ? O6 C13 1.137(5) . ? 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 C11 W C13 89.50(18) . . ? C11 W C12 89.7(2) . . ? C13 W C12 86.82(18) . . ? C11 W C10 86.4(2) . . ? C13 W C10 175.87(18) . . ? C12 W C10 92.5(2) . . ? C11 W C9 89.0(2) . . ? C13 W C9 91.79(19) . . ? C12 W C9 178.14(18) . . ? C10 W C9 88.8(2) . . ? C11 W C1 178.12(18) . . ? C13 W C1 89.48(15) . . ? C12 W C1 91.79(16) . . ? C10 W C1 94.62(17) . . ? C9 W C1 89.43(17) . . ? C1 O1 C7 124.4(3) . . ? C5 N1 C2 108.7(3) . . ? C5 N1 C6 122.6(3) . . ? C2 N1 C6 127.8(3) . . ? O1 C1 C2 107.3(3) . . ? O1 C1 W 128.4(3) . . ? C2 C1 W 124.3(3) . . ? N1 C2 C3 106.9(3) . . ? N1 C2 C1 125.3(3) . . ? C3 C2 C1 127.5(4) . . ? C2 C3 C4 109.0(3) . . ? C5 C4 C3 106.7(3) . . ? N1 C5 C4 108.7(3) . . ? N1 C5 C5 122.2(3) . 2_565 ? C4 C5 C5 129.1(3) . 2_565 ? C8 C7 O1 110.9(4) . . ? O2 C9 W 179.2(5) . . ? O3 C10 W 176.4(5) . . ? O4 C11 W 179.2(5) . . ? O5 C12 W 176.3(4) . . ? O6 C13 W 177.3(4) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.643 _refine_diff_density_min -1.392 _refine_diff_density_rms 0.157 data_FO1543 _database_code_depnum_ccdc_archive 'CCDC 686737' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H8 O7 S W' _chemical_formula_sum 'C15 H8 O7 S W' _chemical_formula_weight 516.12 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall -P2ac2n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 30.1832(9) _cell_length_b 7.4839(2) _cell_length_c 14.6691(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3313.57(16) _cell_formula_units_Z 8 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 10908 _cell_measurement_theta_min 1.94 _cell_measurement_theta_max 27.50 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.069 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1952 _exptl_absorpt_coefficient_mu 7.131 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. R.H. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.536 _exptl_absorpt_correction_T_max 0.584 _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10908 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3994 _reflns_number_gt 3517 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DEMZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.0387P)^2^+13.8287P] 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 3994 _refine_ls_number_parameters 265 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0879 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.001 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 W1A W 0.474079(9) 0.2500 0.748294(18) 0.03023(10) Uani 1 2 d S . . S1A S 0.63343(6) 0.2500 0.68480(12) 0.0321(4) Uani 1 2 d S . . O1A O 0.57435(17) 0.2500 0.8231(3) 0.0351(12) Uani 1 2 d S . . O2A O 0.72069(18) 0.2500 0.5890(4) 0.0466(14) Uani 1 2 d S . . O3A O 0.47623(17) -0.0501(7) 0.5951(3) 0.0630(13) Uani 1 1 d . . . O4A O 0.3695(2) 0.2500 0.7348(5) 0.074(2) Uani 1 2 d S . . O5A O 0.46316(17) -0.0477(7) 0.9011(3) 0.0655(13) Uani 1 1 d . . . C1A C 0.5478(2) 0.2500 0.7509(4) 0.0285(14) Uani 1 2 d S . . C2A C 0.5761(2) 0.2500 0.6726(4) 0.0279(14) Uani 1 2 d S . . C3A C 0.5653(2) 0.2500 0.5798(5) 0.0334(16) Uani 1 2 d S . . H3AA H 0.5357 0.2500 0.5577 0.040 Uiso 1 2 calc SR . . C4A C 0.6021(2) 0.2500 0.5235(5) 0.0378(17) Uani 1 2 d S . . H4AA H 0.6001 0.2500 0.4589 0.045 Uiso 1 2 calc SR . . C5A C 0.6420(2) 0.2500 0.5694(5) 0.0339(16) Uani 1 2 d S . . C6A C 0.6854(2) 0.2500 0.5298(5) 0.0375(17) Uani 1 2 d S . . C7A C 0.6994(3) 0.2500 0.4405(6) 0.065(3) Uani 1 2 d S . . H7AA H 0.6820 0.2500 0.3866 0.078 Uiso 1 2 calc SR . . C8A C 0.7470(3) 0.2500 0.4489(7) 0.070(3) Uani 1 2 d S . . H8AA H 0.7673 0.2500 0.3994 0.084 Uiso 1 2 calc SR . . C9A C 0.7579(3) 0.2500 0.5353(7) 0.047(2) Uani 1 2 d S . . H9AA H 0.7874 0.2500 0.5577 0.056 Uiso 1 2 calc SR . . C10A C 0.5579(3) 0.2500 0.9142(5) 0.053(2) Uani 1 2 d S . . H10A H 0.5828 0.2500 0.9571 0.080 Uiso 1 2 calc SR . . H10B H 0.5397 0.1431 0.9241 0.080 Uiso 0.50 1 calc PR . . H10C H 0.5397 0.3569 0.9241 0.080 Uiso 0.50 1 calc PR . . C12A C 0.47625(19) 0.0560(9) 0.6501(4) 0.0418(13) Uani 1 1 d . . . C13A C 0.4068(3) 0.2500 0.7399(6) 0.048(2) Uani 1 2 d S . . C14A C 0.46843(19) 0.0578(9) 0.8464(4) 0.0433(13) Uani 1 1 d . . . W1B W 0.818303(10) -0.2500 0.63287(2) 0.03352(10) Uani 1 2 d S . . S1B S 0.69967(8) -0.2500 0.66751(19) 0.0575(6) Uani 1 2 d S . . O1B O 0.76552(19) -0.2500 0.4426(4) 0.0532(16) Uani 1 2 d S . . O2B O 0.6280(4) -0.2500 0.7993(5) 0.087(3) Uani 1 2 d S . . O3B O 0.86994(17) 0.0579(7) 0.5297(4) 0.0704(14) Uani 1 1 d . . . O4B O 0.8985(3) -0.2500 0.7719(5) 0.071(2) Uani 1 2 d S . . O5B O 0.77314(18) 0.0470(7) 0.7573(3) 0.0667(15) Uani 1 1 d . . . C1B C 0.7634(2) -0.2500 0.5316(5) 0.0377(17) Uani 1 2 d S . . C2B C 0.7160(3) -0.2500 0.5544(6) 0.0445(19) Uani 1 2 d S . . C3B C 0.6810(3) -0.2500 0.4951(8) 0.065(3) Uani 1 2 d S . . H3BA H 0.6838 -0.2500 0.4306 0.078 Uiso 1 2 calc SR . . C4B C 0.6408(3) -0.2500 0.5410(8) 0.063(3) Uani 1 2 d S . . H4BA H 0.6128 -0.2500 0.5112 0.075 Uiso 1 2 calc SR . . C5B C 0.6454(3) -0.2500 0.6318(7) 0.052(2) Uani 1 2 d S . . C6B C 0.6131(3) -0.2500 0.7033(8) 0.057(2) Uani 1 2 d S . . C7B C 0.5686(3) -0.2500 0.6907(6) 0.0427(19) Uani 1 2 d S . . H7BA H 0.5540 -0.2500 0.6333 0.051 Uiso 1 2 calc SR . . C8B C 0.5479(4) -0.2500 0.7747(8) 0.065(3) Uani 1 2 d S . . H8BA H 0.5169 -0.2500 0.7855 0.078 Uiso 1 2 calc SR . . C9B C 0.5810(6) -0.2500 0.8400(8) 0.094(5) Uani 1 2 d S . . H9BA H 0.5753 -0.2500 0.9037 0.112 Uiso 1 2 calc SR . . C10B C 0.8064(3) -0.2500 0.3920(6) 0.067(3) Uani 1 2 d S . . H10D H 0.7999 -0.2500 0.3266 0.100 Uiso 1 2 calc SR . . H10E H 0.8236 -0.3569 0.4076 0.100 Uiso 0.50 1 calc PR . . H10F H 0.8236 -0.1431 0.4076 0.100 Uiso 0.50 1 calc PR . . C12B C 0.85054(19) -0.0532(8) 0.5649(4) 0.0426(13) Uani 1 1 d . . . C13B C 0.8694(3) -0.2500 0.7226(5) 0.0441(19) Uani 1 2 d S . . C14B C 0.7882(2) -0.0586(9) 0.7103(4) 0.0472(14) 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 W1A 0.02924(16) 0.03918(18) 0.02228(15) 0.000 0.00001(10) 0.000 S1A 0.0292(8) 0.0433(10) 0.0239(8) 0.000 -0.0044(6) 0.000 O1A 0.038(3) 0.051(3) 0.016(2) 0.000 -0.004(2) 0.000 O2A 0.032(3) 0.063(4) 0.045(3) 0.000 -0.001(2) 0.000 O3A 0.081(3) 0.065(3) 0.042(2) -0.021(2) 0.002(2) -0.022(3) O4A 0.034(4) 0.107(7) 0.081(5) 0.000 -0.008(3) 0.000 O5A 0.079(3) 0.068(3) 0.049(3) 0.022(3) 0.017(2) -0.007(3) C1A 0.034(4) 0.027(3) 0.025(3) 0.000 -0.006(3) 0.000 C2A 0.027(3) 0.036(4) 0.021(3) 0.000 -0.003(3) 0.000 C3A 0.023(3) 0.051(5) 0.026(3) 0.000 -0.005(3) 0.000 C4A 0.034(4) 0.061(5) 0.018(3) 0.000 0.000(3) 0.000 C5A 0.034(4) 0.040(4) 0.027(3) 0.000 0.000(3) 0.000 C6A 0.024(3) 0.053(5) 0.035(4) 0.000 -0.003(3) 0.000 C7A 0.040(5) 0.121(10) 0.035(5) 0.000 0.013(4) 0.000 C8A 0.039(5) 0.114(10) 0.058(6) 0.000 0.017(5) 0.000 C9A 0.030(4) 0.048(5) 0.062(6) 0.000 0.005(4) 0.000 C10A 0.047(5) 0.096(8) 0.016(3) 0.000 0.000(3) 0.000 C12A 0.041(3) 0.051(4) 0.033(3) 0.000(3) -0.001(2) -0.012(3) C13A 0.042(5) 0.061(6) 0.040(4) 0.000 0.000(4) 0.000 C14A 0.043(3) 0.049(3) 0.038(3) 0.005(3) 0.009(2) -0.004(3) W1B 0.03722(17) 0.03597(18) 0.02737(16) 0.000 -0.00028(12) 0.000 S1B 0.0361(11) 0.0680(16) 0.0684(15) 0.000 0.0015(11) 0.000 O1B 0.035(3) 0.089(5) 0.036(3) 0.000 -0.001(2) 0.000 O2B 0.151(9) 0.054(5) 0.056(5) 0.000 -0.002(5) 0.000 O3B 0.068(3) 0.054(3) 0.089(4) 0.018(3) 0.025(3) -0.004(3) O4B 0.064(4) 0.102(6) 0.048(4) 0.000 -0.021(3) 0.000 O5B 0.090(4) 0.054(3) 0.056(3) -0.012(2) 0.013(2) 0.013(3) C1B 0.031(4) 0.047(5) 0.035(4) 0.000 0.003(3) 0.000 C2B 0.035(4) 0.046(5) 0.053(5) 0.000 0.001(4) 0.000 C3B 0.037(5) 0.091(8) 0.068(7) 0.000 -0.004(4) 0.000 C4B 0.028(4) 0.084(8) 0.076(7) 0.000 -0.019(4) 0.000 C5B 0.041(5) 0.038(5) 0.078(7) 0.000 -0.015(4) 0.000 C6B 0.057(6) 0.034(5) 0.080(7) 0.000 -0.004(5) 0.000 C7B 0.038(4) 0.051(5) 0.039(4) 0.000 0.002(3) 0.000 C8B 0.066(7) 0.053(6) 0.077(7) 0.000 0.025(6) 0.000 C9B 0.171(16) 0.062(8) 0.048(6) 0.000 -0.001(8) 0.000 C10B 0.055(6) 0.118(10) 0.028(4) 0.000 0.006(4) 0.000 C12B 0.041(3) 0.045(3) 0.042(3) 0.001(3) 0.006(2) 0.005(3) C13B 0.054(5) 0.048(5) 0.031(4) 0.000 -0.008(4) 0.000 C14B 0.061(4) 0.041(3) 0.040(3) 0.006(3) 0.005(3) 0.001(3) _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 W1A C14A 2.042(6) 7_565 ? W1A C14A 2.042(6) . ? W1A C12A 2.046(6) 7_565 ? W1A C12A 2.046(6) . ? W1A C13A 2.036(9) . ? W1A C1A 2.226(7) . ? S1A C5A 1.712(7) . ? S1A C2A 1.739(7) . ? O1A C1A 1.328(8) . ? O1A C10A 1.426(8) . ? O2A C9A 1.371(10) . ? O2A C6A 1.374(9) . ? O3A C12A 1.132(7) . ? O4A C13A 1.126(11) . ? O5A C14A 1.137(7) . ? C1A C2A 1.432(9) . ? C2A C3A 1.399(9) . ? C3A C4A 1.384(10) . ? C4A C5A 1.379(10) . ? C5A C6A 1.432(10) . ? C6A C7A 1.376(11) . ? C7A C8A 1.442(13) . ? C8A C9A 1.310(14) . ? W1B C13B 2.027(8) . ? W1B C12B 2.027(6) . ? W1B C12B 2.027(6) 7 ? W1B C14B 2.041(7) 7 ? W1B C14B 2.041(7) . ? W1B C1B 2.224(8) . ? S1B C2B 1.731(9) . ? S1B C5B 1.719(9) . ? O1B C1B 1.308(9) . ? O1B C10B 1.440(11) . ? O2B C6B 1.478(14) . ? O2B C9B 1.540(19) . ? O3B C12B 1.141(7) . ? O4B C13B 1.137(10) . ? O5B C14B 1.143(7) . ? C1B C2B 1.469(11) . ? C2B C3B 1.370(13) . ? C3B C4B 1.388(14) . ? C4B C5B 1.339(14) . ? C5B C6B 1.431(15) . ? C6B C7B 1.356(13) . ? C7B C8B 1.381(13) . ? C8B C9B 1.384(18) . ? 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 C14A W1A C14A 89.6(3) 7_565 . ? C14A W1A C12A 89.9(3) 7_565 7_565 ? C14A W1A C12A 177.0(2) . 7_565 ? C14A W1A C12A 177.0(2) 7_565 . ? C14A W1A C12A 89.9(3) . . ? C12A W1A C12A 90.4(3) 7_565 . ? C14A W1A C13A 87.7(2) 7_565 . ? C14A W1A C13A 87.7(2) . . ? C12A W1A C13A 89.4(2) 7_565 . ? C12A W1A C13A 89.4(2) . . ? C14A W1A C1A 94.1(2) 7_565 . ? C14A W1A C1A 94.1(2) . . ? C12A W1A C1A 88.86(19) 7_565 . ? C12A W1A C1A 88.86(19) . . ? C13A W1A C1A 177.5(3) . . ? C5A S1A C2A 92.8(3) . . ? C1A O1A C10A 122.5(6) . . ? C9A O2A C6A 105.8(6) . . ? O1A C1A C2A 106.3(6) . . ? O1A C1A W1A 128.1(5) . . ? C2A C1A W1A 125.6(5) . . ? C3A C2A C1A 129.9(6) . . ? C3A C2A S1A 109.4(5) . . ? C1A C2A S1A 120.7(5) . . ? C4A C3A C2A 113.2(6) . . ? C5A C4A C3A 114.2(6) . . ? C4A C5A C6A 126.9(7) . . ? C4A C5A S1A 110.5(5) . . ? C6A C5A S1A 122.6(6) . . ? O2A C6A C7A 111.3(7) . . ? O2A C6A C5A 116.9(7) . . ? C7A C6A C5A 131.8(7) . . ? C6A C7A C8A 103.0(8) . . ? C9A C8A C7A 109.4(8) . . ? C8A C9A O2A 110.5(8) . . ? O3A C12A W1A 178.0(5) . . ? O4A C13A W1A 179.7(8) . . ? O5A C14A W1A 176.7(5) . . ? C13B W1B C12B 87.4(2) . . ? C13B W1B C12B 87.4(2) . 7 ? C12B W1B C12B 93.2(3) . 7 ? C13B W1B C14B 88.7(3) . 7 ? C12B W1B C14B 175.6(2) . 7 ? C12B W1B C14B 88.7(2) 7 7 ? C13B W1B C14B 88.7(3) . . ? C12B W1B C14B 88.7(2) . . ? C12B W1B C14B 175.6(2) 7 . ? C14B W1B C14B 89.1(3) 7 . ? C13B W1B C1B 178.6(3) . . ? C12B W1B C1B 91.7(2) . . ? C12B W1B C1B 91.7(2) 7 . ? C14B W1B C1B 92.3(2) 7 . ? C14B W1B C1B 92.3(2) . . ? C2B S1B C5B 88.9(5) . . ? C1B O1B C10B 123.7(7) . . ? C6B O2B C9B 95.1(9) . . ? O1B C1B C2B 105.9(7) . . ? O1B C1B W1B 129.2(5) . . ? C2B C1B W1B 125.0(6) . . ? C3B C2B C1B 127.4(9) . . ? C3B C2B S1B 112.8(7) . . ? C1B C2B S1B 119.7(6) . . ? C2B C3B C4B 111.6(10) . . ? C5B C4B C3B 113.0(9) . . ? C4B C5B C6B 131.1(9) . . ? C4B C5B S1B 113.8(8) . . ? C6B C5B S1B 115.2(8) . . ? C7B C6B C5B 125.1(10) . . ? C7B C6B O2B 115.5(10) . . ? C5B C6B O2B 119.4(9) . . ? C6B C7B C8B 109.1(9) . . ? C7B C8B C9B 106.9(11) . . ? C8B C9B O2B 113.4(10) . . ? O3B C12B W1B 177.1(6) . . ? O4B C13B W1B 179.0(8) . . ? O5B C14B W1B 176.1(6) . . ? _diffrn_measured_fraction_theta_max 0.974 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.974 _refine_diff_density_max 1.865 _refine_diff_density_min -2.403 _refine_diff_density_rms 0.245 data_FO1542 _database_code_depnum_ccdc_archive 'CCDC 686738' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H13 N O6 S W' _chemical_formula_sum 'C17 H13 N O6 S W' _chemical_formula_weight 543.19 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 '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 _symmetry_space_group_name_Hall -P2ybc 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 7.4036(2) _cell_length_b 12.8191(3) _cell_length_c 19.3686(5) _cell_angle_alpha 90.00 _cell_angle_beta 96.655(2) _cell_angle_gamma 90.00 _cell_volume 1825.84(8) _cell_formula_units_Z 4 _cell_measurement_temperature 183(2) _cell_measurement_reflns_used 18618 _cell_measurement_theta_min 1.91 _cell_measurement_theta_max 27.47 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.976 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 6.474 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; [c.f. R.H. blessing, acta cryst. (1995), a51, 33-38] ; _exptl_absorpt_correction_T_min 0.629 _exptl_absorpt_correction_T_max 0.745 _exptl_special_details ; ? ; _diffrn_ambient_temperature 183(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 KappaCCD _diffrn_measurement_method 'phi- + omega-scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18618 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 27.47 _reflns_number_total 4186 _reflns_number_gt 3448 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement DENZO _computing_data_reduction DENZO _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL/PC _computing_publication_material SHELXL-97 _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^)+(0.0276P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4186 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0268 _refine_ls_wR_factor_ref 0.0590 _refine_ls_wR_factor_gt 0.0550 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _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 W W 0.186292(18) 0.803908(10) 0.286773(7) 0.02323(6) Uani 1 1 d . . . S1 S 0.25084(12) 0.53266(7) 0.46510(4) 0.02285(19) Uani 1 1 d . . . O1 O 0.1872(3) 0.73982(18) 0.44824(11) 0.0261(5) Uani 1 1 d . . . O2 O 0.5553(4) 0.7063(2) 0.24789(16) 0.0442(7) Uani 1 1 d . . . O3 O -0.0579(4) 0.6234(2) 0.21179(16) 0.0519(8) Uani 1 1 d . . . O4 O 0.1514(4) 0.9164(3) 0.14027(15) 0.0563(9) Uani 1 1 d . . . O5 O -0.1763(4) 0.9206(2) 0.31523(14) 0.0443(7) Uani 1 1 d . . . O6 O 0.4254(4) 0.9969(2) 0.34752(15) 0.0448(7) Uani 1 1 d . . . N1 N 0.3050(4) 0.2980(2) 0.53257(15) 0.0261(7) Uani 1 1 d . . . C1 C 0.2106(5) 0.7099(3) 0.38368(18) 0.0220(7) Uani 1 1 d . . . C2 C 0.2491(4) 0.6008(3) 0.38672(16) 0.0224(7) Uani 1 1 d . . . C3 C 0.2872(5) 0.5316(3) 0.33498(18) 0.0255(8) Uani 1 1 d . . . H3A H 0.2930 0.5526 0.2882 0.031 Uiso 1 1 calc R . . C4 C 0.3160(5) 0.4295(3) 0.35731(17) 0.0260(8) Uani 1 1 d . . . H4A H 0.3437 0.3744 0.3274 0.031 Uiso 1 1 calc R . . C5 C 0.3004(4) 0.4154(3) 0.42741(17) 0.0212(7) Uani 1 1 d . . . C6 C 0.3207(5) 0.3165(3) 0.46207(18) 0.0237(8) Uani 1 1 d . . . C7 C 0.3606(5) 0.2214(3) 0.4332(2) 0.0302(8) Uani 1 1 d . . . H7A H 0.3798 0.2097 0.3862 0.036 Uiso 1 1 calc R . . C8 C 0.3675(5) 0.1455(3) 0.48582(19) 0.0325(9) Uani 1 1 d . . . H8A H 0.3907 0.0732 0.4808 0.039 Uiso 1 1 calc R . . C9 C 0.3347(5) 0.1951(3) 0.5454(2) 0.0307(9) Uani 1 1 d . . . H9A H 0.3328 0.1624 0.5893 0.037 Uiso 1 1 calc R . . C10 C 0.2600(5) 0.3729(3) 0.58363(17) 0.0308(8) Uani 1 1 d . . . H10A H 0.2600 0.3382 0.6287 0.046 Uiso 1 1 calc R . . H10B H 0.1393 0.4021 0.5692 0.046 Uiso 1 1 calc R . . H10C H 0.3504 0.4291 0.5876 0.046 Uiso 1 1 calc R . . C11 C 0.1519(5) 0.8469(3) 0.46614(19) 0.0305(8) Uani 1 1 d . . . H11A H 0.0371 0.8714 0.4399 0.037 Uiso 1 1 calc R . . H11B H 0.2521 0.8925 0.4546 0.037 Uiso 1 1 calc R . . C12 C 0.1380(6) 0.8500(3) 0.5429(2) 0.0400(10) Uani 1 1 d . . . H12A H 0.1149 0.9218 0.5569 0.060 Uiso 1 1 calc R . . H12B H 0.2521 0.8252 0.5682 0.060 Uiso 1 1 calc R . . H12C H 0.0378 0.8050 0.5535 0.060 Uiso 1 1 calc R . . C13 C 0.4211(5) 0.7386(3) 0.26246(18) 0.0304(8) Uani 1 1 d . . . C14 C 0.0309(6) 0.6866(3) 0.2392(2) 0.0338(9) Uani 1 1 d . . . C15 C 0.1632(5) 0.8764(3) 0.1939(2) 0.0359(9) Uani 1 1 d . . . C16 C -0.0457(5) 0.8776(3) 0.30705(18) 0.0300(8) Uani 1 1 d . . . C17 C 0.3380(5) 0.9270(3) 0.3277(2) 0.0307(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 W 0.02673(10) 0.01841(9) 0.02476(9) 0.00447(6) 0.00383(6) 0.00082(6) S1 0.0286(5) 0.0188(4) 0.0213(4) 0.0012(3) 0.0031(3) 0.0033(4) O1 0.0376(15) 0.0178(12) 0.0233(12) -0.0014(10) 0.0044(10) 0.0031(11) O2 0.0415(18) 0.0470(19) 0.0474(18) 0.0034(14) 0.0189(15) 0.0080(14) O3 0.049(2) 0.0396(18) 0.063(2) -0.0112(15) -0.0129(15) -0.0068(15) O4 0.055(2) 0.070(2) 0.0444(18) 0.0330(17) 0.0081(15) 0.0014(17) O5 0.0375(17) 0.058(2) 0.0386(16) 0.0142(14) 0.0108(13) 0.0179(15) O6 0.0457(18) 0.0278(16) 0.0604(19) -0.0038(14) 0.0042(14) -0.0057(14) N1 0.0251(16) 0.0279(17) 0.0249(16) 0.0039(12) 0.0009(13) 0.0006(13) C1 0.0194(17) 0.0203(18) 0.0263(18) -0.0020(14) 0.0027(14) -0.0007(14) C2 0.0232(18) 0.0245(19) 0.0191(16) 0.0045(14) 0.0014(13) 0.0003(15) C3 0.032(2) 0.0204(18) 0.0243(18) 0.0018(14) 0.0030(15) 0.0042(15) C4 0.033(2) 0.0215(19) 0.0244(18) -0.0008(15) 0.0066(15) 0.0042(15) C5 0.0194(17) 0.0190(17) 0.0248(17) -0.0027(14) 0.0008(13) -0.0003(14) C6 0.0196(18) 0.025(2) 0.0264(19) 0.0012(14) 0.0026(14) -0.0013(14) C7 0.033(2) 0.026(2) 0.032(2) 0.0020(16) 0.0042(17) 0.0022(16) C8 0.037(2) 0.0191(19) 0.042(2) 0.0065(17) 0.0048(17) -0.0012(17) C9 0.029(2) 0.027(2) 0.035(2) 0.0122(16) -0.0003(16) 0.0009(16) C10 0.035(2) 0.033(2) 0.0244(19) 0.0054(16) 0.0047(16) 0.0023(17) C11 0.039(2) 0.0189(19) 0.034(2) -0.0059(16) 0.0054(16) 0.0047(16) C12 0.044(3) 0.040(2) 0.037(2) -0.0102(19) 0.0053(18) 0.007(2) C13 0.039(2) 0.027(2) 0.0263(19) 0.0045(16) 0.0072(17) -0.0005(18) C14 0.038(2) 0.032(2) 0.031(2) 0.0054(17) -0.0013(18) 0.0074(18) C15 0.036(2) 0.034(2) 0.038(2) 0.0067(18) 0.0070(18) -0.0010(18) C16 0.036(2) 0.031(2) 0.0226(18) 0.0085(15) 0.0021(16) 0.0009(17) C17 0.030(2) 0.024(2) 0.039(2) 0.0074(17) 0.0076(16) 0.0059(17) _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 W C15 2.015(4) . ? W C13 2.033(4) . ? W C16 2.038(4) . ? W C17 2.044(4) . ? W C14 2.046(4) . ? W C1 2.221(3) . ? S1 C5 1.729(3) . ? S1 C2 1.750(3) . ? O1 C1 1.338(4) . ? O1 C11 1.446(4) . ? O2 C13 1.142(5) . ? O3 C14 1.136(5) . ? O4 C15 1.152(4) . ? O5 C16 1.140(5) . ? O6 C17 1.145(4) . ? N1 C9 1.355(4) . ? N1 C6 1.404(4) . ? N1 C10 1.444(5) . ? C1 C2 1.427(5) . ? C2 C3 1.391(5) . ? C3 C4 1.387(5) . ? C4 C5 1.387(5) . ? C5 C6 1.435(5) . ? C6 C7 1.387(5) . ? C7 C8 1.406(5) . ? C8 C9 1.364(5) . ? C11 C12 1.502(5) . ? 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 C15 W C13 88.23(16) . . ? C15 W C16 88.41(15) . . ? C13 W C16 176.17(14) . . ? C15 W C17 88.66(15) . . ? C13 W C17 87.79(15) . . ? C16 W C17 90.28(15) . . ? C15 W C14 87.23(16) . . ? C13 W C14 92.56(16) . . ? C16 W C14 89.12(16) . . ? C17 W C14 175.86(14) . . ? C15 W C1 174.57(14) . . ? C13 W C1 89.12(13) . . ? C16 W C1 94.38(13) . . ? C17 W C1 95.97(13) . . ? C14 W C1 88.16(14) . . ? C5 S1 C2 92.74(17) . . ? C1 O1 C11 122.9(3) . . ? C9 N1 C6 108.2(3) . . ? C9 N1 C10 124.5(3) . . ? C6 N1 C10 127.2(3) . . ? O1 C1 C2 106.8(3) . . ? O1 C1 W 128.8(2) . . ? C2 C1 W 124.3(2) . . ? C3 C2 C1 130.6(3) . . ? C3 C2 S1 109.0(3) . . ? C1 C2 S1 120.4(3) . . ? C2 C3 C4 114.4(3) . . ? C5 C4 C3 113.6(3) . . ? C4 C5 C6 123.8(3) . . ? C4 C5 S1 110.3(3) . . ? C6 C5 S1 125.9(3) . . ? C7 C6 N1 106.8(3) . . ? C7 C6 C5 127.1(3) . . ? N1 C6 C5 126.1(3) . . ? C6 C7 C8 107.9(3) . . ? C9 C8 C7 107.2(3) . . ? C8 C9 N1 109.8(3) . . ? O1 C11 C12 107.3(3) . . ? O2 C13 W 176.9(3) . . ? O3 C14 W 178.2(3) . . ? O4 C15 W 178.9(4) . . ? O5 C16 W 176.7(3) . . ? O6 C17 W 176.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.549 _refine_diff_density_min -1.001 _refine_diff_density_rms 0.137