# Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 186/1840 data_2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H23 N O9 S U' _chemical_formula_weight 607.41 _chemical_melting_point ? _chemical_compound_source ? 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' 'U' 'U' -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 20.160(3) _cell_length_b 17.502(3) _cell_length_c 10.3781(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3661.8(9) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.204 _exptl_crystal_density_method ? _exptl_crystal_F_000 2304 _exptl_absorpt_coefficient_mu 9.025 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3401 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0275 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 1 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3209 _reflns_number_observed 2549 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0615P)^2^+2.1298P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3209 _refine_ls_number_parameters 228 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0480 _refine_ls_R_factor_obs 0.0338 _refine_ls_wR_factor_all 0.0905 _refine_ls_wR_factor_obs 0.0865 _refine_ls_goodness_of_fit_all 1.060 _refine_ls_goodness_of_fit_obs 1.148 _refine_ls_restrained_S_all 1.060 _refine_ls_restrained_S_obs 1.148 _refine_ls_shift/esd_max 0.351 _refine_ls_shift/esd_mean 0.007 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group U1A U 0.415947(12) 1.053998(12) -0.01705(2) 0.01035(11) Uani 1 d . . S1 S 0.26514(8) 0.98727(10) -0.1756(2) 0.0207(4) Uani 1 d . . O2 O 0.5259(2) 1.0598(2) 0.0570(5) 0.0129(10) Uani 1 d . . O1 O 0.3298(2) 1.1320(3) -0.0301(5) 0.0209(11) Uani 1 d . . O7 O 0.5440(3) 1.2974(3) 0.0780(5) 0.0240(11) Uani 1 d . . H7 H 0.5452(41) 1.3444(3) 0.0940(7) 0.036 Uiso 1 calc R . O6 O 0.4613(2) 1.1665(3) 0.3858(5) 0.0243(11) Uani 1 d . . H6 H 0.4826(6) 1.1949(37) 0.4362(50) 0.036 Uiso 1 calc R . O5 O 0.3338(2) 0.9751(3) -0.1188(5) 0.0242(12) Uani 1 d . . O3 O 0.3886(2) 1.0157(2) 0.1343(4) 0.0133(10) Uani 1 d . . C1 C 0.2976(3) 1.1884(4) 0.0299(7) 0.0169(15) Uani 1 d . . O4 O 0.4444(2) 1.0927(2) -0.1668(5) 0.0193(11) Uani 1 d . . N1 N 0.4406(3) 1.1769(3) 0.1139(5) 0.0130(12) Uani 1 d . . C2 C 0.2290(4) 1.1986(4) 0.0069(6) 0.020(2) Uani 1 d . . H2 H 0.2066(4) 1.1658(4) -0.0515(6) 0.024 Uiso 1 calc R . C6 C 0.3307(3) 1.2371(3) 0.1149(6) 0.0155(14) Uani 1 d . . C9 C 0.5523(3) 1.1339(3) 0.0736(7) 0.0148(14) Uani 1 d . . H9A H 0.5530(3) 1.1612(3) -0.0100(7) 0.018 Uiso 1 calc R . H9B H 0.5983(3) 1.1307(3) 0.1065(7) 0.018 Uiso 1 calc R . C4 C 0.2268(4) 1.3043(4) 0.1541(7) 0.025(2) Uani 1 d . . H4 H 0.2029(4) 1.3433(4) 0.1974(7) 0.030 Uiso 1 calc R . C5 C 0.2936(3) 1.2952(4) 0.1759(7) 0.020(2) Uani 1 d . . H5 H 0.3155(3) 1.3290(4) 0.2336(7) 0.024 Uiso 1 calc R . C11 C 0.5389(3) 1.2561(3) 0.1947(7) 0.0167(15) Uani 1 d . . H11A H 0.5110(3) 1.2849(3) 0.2564(7) 0.020 Uiso 1 calc R . H11B H 0.5836(3) 1.2501(3) 0.2333(7) 0.020 Uiso 1 calc R . C7 C 0.3995(3) 1.2298(4) 0.1479(6) 0.0139(14) Uani 1 d . . H7 H 0.4170(3) 1.2689(4) 0.2015(6) 0.017 Uiso 1 calc R . C3 C 0.1946(3) 1.2561(4) 0.0686(7) 0.021(2) Uani 1 d . . H3 H 0.1486(3) 1.2627(4) 0.0524(7) 0.025 Uiso 1 calc R . C8 C 0.5084(3) 1.1773(3) 0.1703(6) 0.0129(14) Uani 1 d . . C10 C 0.5050(3) 1.1331(4) 0.2972(6) 0.0176(15) Uani 1 d . . H10A H 0.4906(3) 1.0801(4) 0.2795(6) 0.021 Uiso 1 calc R . H10B H 0.5499(3) 1.1308(4) 0.3358(6) 0.021 Uiso 1 calc R . C12 C 0.2259(4) 0.8970(4) -0.1583(7) 0.027(2) Uani 1 d . . H12A H 0.2155(4) 0.8881(4) -0.0672(7) 0.041 Uiso 1 calc R . H12B H 0.2557(4) 0.8567(4) -0.1891(7) 0.041 Uiso 1 calc R . H12C H 0.1849(4) 0.8962(4) -0.2089(7) 0.041 Uiso 1 calc R . C13 C 0.2776(4) 0.9875(5) -0.3429(8) 0.036(2) Uani 1 d . . H13A H 0.2995(4) 1.0351(5) -0.3684(8) 0.054 Uiso 1 calc R . H13B H 0.2346(4) 0.9835(5) -0.3868(8) 0.054 Uiso 1 calc R . H13C H 0.3055(4) 0.9439(5) -0.3671(8) 0.054 Uiso 1 calc R . OW1 O 0.4144(3) 1.0530(3) 0.5492(7) 0.040(2) Uani 1 d . . HW1A H 0.4390(3) 1.0533(3) 0.6393(7) 0.060 Uiso 1 d R . HW1B H 0.4390(3) 1.0891(3) 0.5111(7) 0.060 Uiso 1 d R . OW2 O 0.4022(3) 0.9349(3) 0.3772(6) 0.044(2) Uani 1 d . . HW2A H 0.3893(3) 0.9418(3) 0.2929(6) 0.066 Uiso 1 d R . HW2B H 0.4493(3) 0.9501(3) 0.3613(6) 0.066 Uiso 1 d 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 U1A 0.0124(2) 0.0106(2) 0.0081(2) -0.00155(9) -0.00118(9) 0.00038(9) S1 0.0183(10) 0.0202(9) 0.0237(10) -0.0032(7) -0.0073(7) 0.0010(7) O2 0.013(2) 0.009(2) 0.017(3) -0.004(2) 0.002(2) 0.004(2) O1 0.018(3) 0.017(2) 0.028(3) -0.006(2) -0.008(2) 0.003(2) O7 0.039(3) 0.012(2) 0.020(3) 0.004(2) -0.007(2) -0.007(2) O6 0.030(3) 0.030(3) 0.013(3) -0.005(2) 0.002(2) 0.001(2) O5 0.021(3) 0.019(2) 0.032(3) -0.008(2) -0.019(2) 0.002(2) O3 0.017(2) 0.011(2) 0.012(2) -0.003(2) 0.003(2) -0.005(2) C1 0.017(4) 0.016(3) 0.017(4) 0.003(3) -0.003(3) 0.005(3) O4 0.024(3) 0.020(2) 0.014(3) -0.001(2) 0.005(2) 0.001(2) N1 0.015(3) 0.013(3) 0.011(3) -0.003(2) -0.004(2) -0.001(2) C2 0.017(4) 0.028(4) 0.015(4) 0.003(3) -0.005(3) -0.001(3) C6 0.022(4) 0.011(3) 0.013(4) 0.006(3) 0.000(3) 0.002(3) C9 0.014(3) 0.010(3) 0.020(4) -0.001(3) -0.001(3) -0.005(3) C4 0.026(4) 0.026(4) 0.023(4) 0.001(3) 0.007(3) 0.012(3) C5 0.027(4) 0.018(4) 0.014(4) 0.003(3) 0.002(3) -0.004(3) C11 0.019(4) 0.011(3) 0.020(4) -0.005(3) -0.006(3) -0.003(3) C7 0.017(4) 0.013(3) 0.012(3) -0.004(3) 0.000(3) 0.001(3) C3 0.017(4) 0.032(4) 0.014(4) 0.009(3) 0.003(3) 0.006(3) C8 0.017(3) 0.009(3) 0.013(4) -0.001(3) -0.006(3) 0.000(3) C10 0.025(4) 0.015(3) 0.012(3) 0.001(3) 0.000(3) 0.001(3) C12 0.027(4) 0.031(4) 0.023(4) 0.000(3) -0.005(3) -0.009(3) C13 0.037(5) 0.049(5) 0.020(5) 0.004(4) -0.006(4) -0.006(4) OW1 0.055(4) 0.035(3) 0.030(3) 0.006(3) 0.008(3) -0.014(3) OW2 0.077(5) 0.025(3) 0.030(4) 0.008(3) -0.002(3) 0.013(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 U1A O4 1.791(5) . ? U1A O3 1.795(4) . ? U1A O1 2.213(5) . ? U1A O2 2.348(4) . ? U1A O2 2.347(4) 5_675 ? U1A O5 2.400(4) . ? U1A N1 2.593(5) . ? U1A U1A 3.8965(6) 5_675 ? S1 O5 1.520(5) . ? S1 C13 1.755(8) . ? S1 C12 1.776(7) . ? O2 C9 1.413(7) . ? O2 U1A 2.347(4) 5_675 ? O1 C1 1.336(8) . ? O7 C11 1.414(8) . ? O6 C10 1.402(8) . ? C1 C6 1.396(9) . ? C1 C2 1.414(10) . ? N1 C7 1.292(8) . ? N1 C8 1.487(8) . ? C2 C3 1.379(10) . ? C6 C5 1.412(9) . ? C6 C7 1.433(9) . ? C9 C8 1.538(9) . ? C4 C5 1.375(10) . ? C4 C3 1.386(10) . ? C11 C8 1.532(8) . ? C8 C10 1.529(9) . ? 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 O4 U1A O3 179.1(2) . . ? O4 U1A O1 88.0(2) . . ? O3 U1A O1 92.5(2) . . ? O4 U1A O2 88.0(2) . . ? O3 U1A O2 91.1(2) . . ? O1 U1A O2 137.3(2) . . ? O4 U1A O2 90.4(2) . 5_675 ? O3 U1A O2 89.5(2) . 5_675 ? O1 U1A O2 154.7(2) . 5_675 ? O2 U1A O2 67.8(2) . 5_675 ? O4 U1A O5 93.3(2) . . ? O3 U1A O5 87.6(2) . . ? O1 U1A O5 77.7(2) . . ? O2 U1A O5 145.06(15) . . ? O2 U1A O5 77.2(2) 5_675 . ? O4 U1A N1 94.6(2) . . ? O3 U1A N1 84.8(2) . . ? O1 U1A N1 70.8(2) . . ? O2 U1A N1 67.2(2) . . ? O2 U1A N1 134.5(2) 5_675 . ? O5 U1A N1 147.1(2) . . ? O4 U1A U1A 89.05(15) . 5_675 ? O3 U1A U1A 90.37(14) . 5_675 ? O1 U1A U1A 170.87(12) . 5_675 ? O2 U1A U1A 33.91(9) . 5_675 ? O2 U1A U1A 33.92(11) 5_675 5_675 ? O5 U1A U1A 111.16(11) . 5_675 ? N1 U1A U1A 100.85(12) . 5_675 ? O5 S1 C13 104.7(4) . . ? O5 S1 C12 104.0(3) . . ? C13 S1 C12 99.5(4) . . ? C9 O2 U1A 115.8(3) . . ? C9 O2 U1A 127.8(4) . 5_675 ? U1A O2 U1A 112.2(2) . 5_675 ? C1 O1 U1A 143.9(4) . . ? S1 O5 U1A 135.9(3) . . ? O1 C1 C6 120.9(6) . . ? O1 C1 C2 119.3(6) . . ? C6 C1 C2 119.8(6) . . ? C7 N1 C8 118.7(5) . . ? C7 N1 U1A 127.9(4) . . ? C8 N1 U1A 112.7(3) . . ? C3 C2 C1 120.4(7) . . ? C1 C6 C5 118.0(6) . . ? C1 C6 C7 124.0(6) . . ? C5 C6 C7 117.9(6) . . ? O2 C9 C8 108.5(5) . . ? C5 C4 C3 119.6(7) . . ? C4 C5 C6 121.8(7) . . ? O7 C11 C8 110.3(5) . . ? N1 C7 C6 128.3(6) . . ? C2 C3 C4 120.4(6) . . ? N1 C8 C10 107.2(5) . . ? N1 C8 C11 116.0(5) . . ? C10 C8 C11 109.3(5) . . ? N1 C8 C9 105.6(5) . . ? C10 C8 C9 109.8(5) . . ? C11 C8 C9 108.8(5) . . ? O6 C10 C8 112.4(5) . . ? _refine_diff_density_max 1.482 _refine_diff_density_min -2.365 _refine_diff_density_rms 0.242 data_1.bipy _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C44 H50 N4 O14 S2 U2' _chemical_formula_weight 1399.06 _chemical_melting_point ? _chemical_compound_source ? 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'U' 'U' -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 16.775 _cell_length_b 7.762 _cell_length_c 17.891 _cell_angle_alpha 90.00 _cell_angle_beta 101.07 _cell_angle_gamma 90.00 _cell_volume 2286.2 _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.032 _exptl_crystal_density_method ? _exptl_crystal_F_000 1340 _exptl_absorpt_coefficient_mu 7.238 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4137 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0816 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 24.98 _reflns_number_total 3991 _reflns_number_observed 2649 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0301P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3991 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_obs 0.0307 _refine_ls_wR_factor_all 0.0648 _refine_ls_wR_factor_obs 0.0599 _refine_ls_goodness_of_fit_all 0.932 _refine_ls_goodness_of_fit_obs 1.079 _refine_ls_restrained_S_all 0.932 _refine_ls_restrained_S_obs 1.079 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group U1 U 0.42989(2) 0.12476(3) 0.056956(15) 0.01353(8) Uani 1 d . . S1 S 0.49319(12) 0.5432(2) 0.13375(10) 0.0222(4) Uani 1 d . . O5 O 0.5012(3) 0.3445(6) 0.1395(3) 0.0251(12) Uani 1 d . . O4 O 0.4526(3) -0.0171(6) 0.1369(2) 0.0169(11) Uani 1 d . . O2 O 0.4377(3) -0.0818(6) -0.0375(2) 0.0147(11) Uani 1 d . . O3 O 0.4054(3) 0.2742(6) -0.0195(3) 0.0225(12) Uani 1 d . . O1 O 0.3229(3) 0.2503(6) 0.0987(3) 0.0184(11) Uani 1 d . . N1 N 0.3029(3) -0.0615(7) 0.0207(3) 0.0124(12) Uani 1 d . . C13 C 0.3626(4) -0.1044(11) -0.0897(4) 0.021(2) Uani 1 d . . H13A H 0.3701(4) -0.1849(11) -0.1307(4) 0.025 Uiso 1 calc R . H13B H 0.3438(4) 0.0075(11) -0.1132(4) 0.025 Uiso 1 calc R . C9 C 0.1808(4) -0.0388(10) 0.1717(4) 0.017(2) Uani 1 d . . C10 C 0.2365(4) 0.0237(9) 0.1262(4) 0.014(2) Uani 1 d . . C1 C 0.2709(4) 0.1869(9) 0.1395(4) 0.018(2) Uani 1 d . . O6 O 0.2753(3) -0.4279(6) 0.0257(3) 0.0269(13) Uani 1 d . . H6 H 0.2927(30) -0.5251(49) 0.0418(39) 0.040 Uiso 1 calc R . O7 O 0.1834(3) -0.0241(7) -0.1243(3) 0.0278(13) Uani 1 d . . H7 H 0.1499(39) 0.0057(50) -0.0973(32) 0.042 Uiso 1 calc R . N2 N 0.0805(4) 0.1169(10) -0.0329(3) 0.0299(15) Uani 1 d . . C14 C 0.3260(4) -0.3593(10) -0.0217(4) 0.021(2) Uani 1 d . . H14A H 0.3234(4) -0.4339(10) -0.0669(4) 0.025 Uiso 1 calc R . H14B H 0.3829(4) -0.3575(10) 0.0064(4) 0.025 Uiso 1 calc R . C17 C 0.5865(4) 0.6195(12) 0.1899(4) 0.026(2) Uani 1 d . . H17A H 0.6310(4) 0.5981(12) 0.1628(4) 0.038 Uiso 1 calc R . H17B H 0.5973(4) 0.5587(12) 0.2388(4) 0.038 Uiso 1 calc R . H17C H 0.5823(4) 0.7434(12) 0.1989(4) 0.038 Uiso 1 calc R . C11 C 0.2466(4) -0.0762(8) 0.0590(4) 0.017(2) Uani 1 d . . H11 H 0.2066(4) -0.1615(8) 0.0422(4) 0.020 Uiso 1 calc R . C2 C 0.2461(4) 0.2929(10) 0.1948(4) 0.022(2) Uani 1 d . . H2 H 0.2690(4) 0.4049(10) 0.2031(4) 0.026 Uiso 1 calc R . C16 C 0.4266(5) 0.5974(9) 0.1952(4) 0.026(2) Uani 1 d . . H16A H 0.3711(5) 0.5629(9) 0.1719(4) 0.039 Uiso 1 calc R . H16B H 0.4282(5) 0.7221(9) 0.2039(4) 0.039 Uiso 1 calc R . H16C H 0.4432(5) 0.5374(9) 0.2438(4) 0.039 Uiso 1 calc R . C12 C 0.2996(4) -0.1762(9) -0.0472(4) 0.018(2) Uani 1 d . . C6 C 0.0667(5) -0.1459(12) 0.2586(4) 0.031(2) Uani 1 d . . H6 H 0.0256(5) -0.1802(12) 0.2854(4) 0.037 Uiso 1 calc R . C15 C 0.2157(4) -0.1871(9) -0.1004(4) 0.019(2) Uani 1 d . . H15A H 0.2206(4) -0.2563(9) -0.1458(4) 0.022 Uiso 1 calc R . H15B H 0.1775(4) -0.2475(9) -0.0735(4) 0.022 Uiso 1 calc R . C8 C 0.1499(5) -0.2090(11) 0.1672(5) 0.027(2) Uani 1 d . . H8 H 0.1681(5) -0.2895(11) 0.1341(5) 0.032 Uiso 1 calc R . C4 C 0.1570(4) 0.0739(10) 0.2255(4) 0.022(2) Uani 1 d . . C3 C 0.1920(5) 0.2422(10) 0.2360(4) 0.025(2) Uani 1 d . . H3 H 0.1766(5) 0.3181(10) 0.2724(4) 0.030 Uiso 1 calc R . C5 C 0.0993(5) 0.0179(10) 0.2684(4) 0.024(2) Uani 1 d . . H5 H 0.0828(5) 0.0936(10) 0.3043(4) 0.029 Uiso 1 calc R . C22 C 0.0214(4) 0.0845(10) 0.0065(4) 0.025(2) Uani 1 d . . C19 C 0.1025(5) 0.3910(13) 0.0283(5) 0.040(2) Uani 1 d . . H19 H 0.1311(5) 0.4973(13) 0.0340(5) 0.048 Uiso 1 calc R . C20 C 0.0430(5) 0.3567(13) 0.0691(5) 0.040(2) Uani 1 d . . H20 H 0.0294(5) 0.4401(13) 0.1035(5) 0.049 Uiso 1 calc R . C21 C 0.0028(5) 0.2006(11) 0.0601(5) 0.032(2) Uani 1 d . . H21 H -0.0367(5) 0.1729(11) 0.0898(5) 0.038 Uiso 1 calc R . C18 C 0.1193(5) 0.2671(11) -0.0208(5) 0.033(2) Uani 1 d . . H18 H 0.1614(5) 0.2897(11) -0.0482(5) 0.040 Uiso 1 calc R . C7 C 0.0941(5) -0.2596(11) 0.2097(4) 0.036(2) Uani 1 d . . H7 H 0.0741(5) -0.3744(11) 0.2055(4) 0.043 Uiso 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 U1 0.01456(12) 0.01084(11) 0.01547(12) -0.0018(2) 0.00358(8) -0.0020(2) S1 0.0292(11) 0.0192(10) 0.0167(9) -0.0017(8) 0.0005(8) -0.0056(9) O5 0.023(3) 0.020(3) 0.030(3) -0.010(2) 0.001(2) -0.004(2) O4 0.022(3) 0.017(3) 0.012(2) 0.000(2) 0.003(2) 0.002(2) O2 0.019(3) 0.016(3) 0.007(2) -0.007(2) -0.004(2) -0.004(2) O3 0.032(3) 0.017(3) 0.019(3) 0.005(2) 0.008(2) 0.003(2) O1 0.019(3) 0.017(3) 0.021(3) -0.001(2) 0.006(2) -0.002(2) N1 0.009(3) 0.012(3) 0.015(3) 0.001(2) 0.000(2) 0.002(2) C13 0.017(4) 0.027(4) 0.017(3) -0.008(4) 0.001(3) 0.004(4) C9 0.009(4) 0.021(4) 0.022(4) 0.000(3) 0.006(3) 0.001(3) C10 0.010(4) 0.016(4) 0.014(4) 0.002(3) -0.002(3) 0.005(3) C1 0.012(4) 0.021(4) 0.019(4) -0.002(3) -0.003(3) 0.007(3) O6 0.031(3) 0.015(3) 0.039(3) 0.011(2) 0.016(3) 0.007(2) O7 0.025(3) 0.030(3) 0.029(3) 0.007(3) 0.005(3) 0.009(3) N2 0.023(3) 0.032(4) 0.034(4) -0.003(4) 0.007(3) 0.006(4) C14 0.019(4) 0.016(4) 0.027(4) -0.008(4) 0.006(3) -0.001(4) C17 0.024(4) 0.027(4) 0.027(4) -0.011(4) 0.006(3) -0.007(4) C11 0.010(4) 0.011(4) 0.028(4) 0.005(3) 0.003(3) -0.003(3) C2 0.016(4) 0.017(4) 0.033(4) -0.005(4) 0.005(3) -0.008(3) C16 0.031(4) 0.013(4) 0.034(4) 0.001(4) 0.006(4) -0.004(4) C12 0.019(4) 0.019(4) 0.014(4) -0.002(3) 0.000(3) 0.001(3) C6 0.022(4) 0.043(6) 0.029(4) 0.002(4) 0.012(3) -0.009(4) C15 0.016(4) 0.019(4) 0.021(4) -0.006(3) 0.004(3) -0.003(3) C8 0.028(5) 0.026(4) 0.030(5) -0.008(4) 0.013(4) -0.003(4) C4 0.015(4) 0.028(5) 0.023(4) 0.003(3) 0.002(3) 0.001(3) C3 0.025(5) 0.031(5) 0.018(4) -0.004(4) 0.004(3) 0.008(4) C5 0.022(4) 0.031(5) 0.018(4) -0.003(4) 0.000(3) -0.003(4) C22 0.019(4) 0.033(5) 0.022(4) -0.002(4) -0.001(3) -0.001(4) C19 0.036(5) 0.037(5) 0.046(5) -0.012(5) 0.006(4) -0.012(5) C20 0.038(5) 0.044(6) 0.040(5) -0.017(5) 0.007(4) -0.005(5) C21 0.022(5) 0.037(5) 0.036(5) -0.011(4) 0.003(4) -0.003(4) C18 0.030(5) 0.031(5) 0.038(5) 0.003(4) 0.004(4) 0.001(4) C7 0.040(6) 0.038(5) 0.036(5) -0.005(4) 0.022(4) -0.022(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U1 O3 1.781(5) . ? U1 O4 1.787(5) . ? U1 O1 2.290(5) . ? U1 O2 2.336(5) 3_655 ? U1 O2 2.352(4) . ? U1 O5 2.417(5) . ? U1 N1 2.553(5) . ? U1 U1 3.9088(5) 3_655 ? S1 O5 1.550(5) . ? S1 C16 1.762(7) . ? S1 C17 1.790(7) . ? O2 C13 1.428(8) . ? O2 U1 2.336(5) 3_655 ? O1 C1 1.335(8) . ? N1 C11 1.275(8) . ? N1 C12 1.498(8) . ? C13 C12 1.521(9) . ? C9 C4 1.414(10) . ? C9 C8 1.415(10) . ? C9 C10 1.437(9) . ? C10 C1 1.393(10) . ? C10 C11 1.467(9) . ? C1 C2 1.409(10) . ? O6 C14 1.416(8) . ? O7 C15 1.410(8) . ? N2 C18 1.333(11) . ? N2 C22 1.346(9) . ? C14 C12 1.532(10) . ? C2 C3 1.335(10) . ? C12 C15 1.542(10) . ? C6 C5 1.381(12) . ? C6 C7 1.382(11) . ? C8 C7 1.372(10) . ? C4 C5 1.414(10) . ? C4 C3 1.430(11) . ? C22 C21 1.394(10) . ? C22 C22 1.491(15) 3 ? C19 C18 1.369(11) . ? C19 C20 1.370(11) . ? C20 C21 1.381(12) . ? 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 O3 U1 O4 177.0(2) . . ? O3 U1 O1 83.9(2) . . ? O4 U1 O1 93.5(2) . . ? O3 U1 O2 93.7(2) . 3_655 ? O4 U1 O2 88.2(2) . 3_655 ? O1 U1 O2 159.4(2) . 3_655 ? O3 U1 O2 85.9(2) . . ? O4 U1 O2 97.0(2) . . ? O1 U1 O2 132.8(2) . . ? O2 U1 O2 67.0(2) 3_655 . ? O3 U1 O5 91.4(2) . . ? O4 U1 O5 86.7(2) . . ? O1 U1 O5 80.1(2) . . ? O2 U1 O5 79.5(2) 3_655 . ? O2 U1 O5 146.2(2) . . ? O3 U1 N1 96.6(2) . . ? O4 U1 N1 83.9(2) . . ? O1 U1 N1 69.9(2) . . ? O2 U1 N1 130.7(2) 3_655 . ? O2 U1 N1 65.8(2) . . ? O5 U1 N1 147.8(2) . . ? O3 U1 U1 89.7(2) . 3_655 ? O4 U1 U1 93.14(15) . 3_655 ? O1 U1 U1 165.62(12) . 3_655 ? O2 U1 U1 33.63(10) 3_655 3_655 ? O2 U1 U1 33.39(11) . 3_655 ? O5 U1 U1 113.03(11) . 3_655 ? N1 U1 U1 98.23(12) . 3_655 ? O5 S1 C16 104.7(3) . . ? O5 S1 C17 103.7(4) . . ? C16 S1 C17 99.3(3) . . ? S1 O5 U1 129.4(3) . . ? C13 O2 U1 129.1(3) . 3_655 ? C13 O2 U1 112.9(4) . . ? U1 O2 U1 113.0(2) 3_655 . ? C1 O1 U1 131.1(4) . . ? C11 N1 C12 117.9(6) . . ? C11 N1 U1 125.6(5) . . ? C12 N1 U1 116.2(4) . . ? O2 C13 C12 109.2(5) . . ? C4 C9 C8 117.9(7) . . ? C4 C9 C10 118.4(7) . . ? C8 C9 C10 123.6(7) . . ? C1 C10 C9 120.2(7) . . ? C1 C10 C11 120.8(6) . . ? C9 C10 C11 118.4(6) . . ? O1 C1 C10 122.3(6) . . ? O1 C1 C2 118.7(6) . . ? C10 C1 C2 118.9(7) . . ? C18 N2 C22 117.8(7) . . ? O6 C14 C12 110.8(5) . . ? N1 C11 C10 127.4(6) . . ? C3 C2 C1 122.6(7) . . ? N1 C12 C13 105.4(5) . . ? N1 C12 C14 110.2(5) . . ? C13 C12 C14 107.5(6) . . ? N1 C12 C15 114.8(6) . . ? C13 C12 C15 110.6(5) . . ? C14 C12 C15 108.1(6) . . ? C5 C6 C7 119.7(7) . . ? O7 C15 C12 113.0(6) . . ? C7 C8 C9 121.1(7) . . ? C9 C4 C5 119.4(7) . . ? C9 C4 C3 119.5(7) . . ? C5 C4 C3 121.1(7) . . ? C2 C3 C4 120.2(7) . . ? C6 C5 C4 120.6(7) . . ? N2 C22 C21 121.5(7) . . ? N2 C22 C22 117.6(8) . 3 ? C21 C22 C22 120.8(8) . 3 ? C18 C19 C20 117.8(9) . . ? C19 C20 C21 119.8(8) . . ? C20 C21 C22 118.7(7) . . ? N2 C18 C19 124.3(8) . . ? C8 C7 C6 120.9(8) . . ? _refine_diff_density_max 1.365 _refine_diff_density_min -0.859 _refine_diff_density_rms 0.173 data_5 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H19 N O7 S U' _chemical_formula_weight 583.39 _chemical_melting_point ? _chemical_compound_source ? 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' 'U' 'U' -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 12.010(3) _cell_length_b 16.968(2) _cell_length_c 17.342(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3534.1(11) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.193 _exptl_crystal_density_method ? _exptl_crystal_F_000 2192 _exptl_absorpt_coefficient_mu 9.338 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3315 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0407 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 24.96 _reflns_number_total 3097 _reflns_number_observed 2240 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0510P)^2^+16.7596P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3097 _refine_ls_number_parameters 216 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_obs 0.0349 _refine_ls_wR_factor_all 0.0936 _refine_ls_wR_factor_obs 0.0889 _refine_ls_goodness_of_fit_all 1.054 _refine_ls_goodness_of_fit_obs 1.194 _refine_ls_restrained_S_all 1.054 _refine_ls_restrained_S_obs 1.194 _refine_ls_shift/esd_max 0.359 _refine_ls_shift/esd_mean 0.009 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group U1 U 0.01412(2) 0.58858(2) 0.07173(2) 0.01713(12) Uani 1 d . . O1 O -0.0090(5) 0.6922(3) 0.1516(3) 0.0279(14) Uani 1 d . . O2 O -0.0969(4) 0.5260(3) -0.0214(3) 0.0222(13) Uani 1 d . . C2 C 0.0025(6) 0.8212(5) 0.2029(5) 0.026(2) Uani 1 d . . O5 O -0.0589(6) 0.5314(3) 0.1415(3) 0.0322(15) Uani 1 d . . O6 O 0.0885(5) 0.6467(3) 0.0040(3) 0.0275(14) Uani 1 d . . O7 O 0.1819(6) 0.5774(4) 0.1451(4) 0.049(2) Uani 1 d . . N1 N -0.1573(6) 0.6703(4) 0.0294(4) 0.024(2) Uani 1 d . . C1 C -0.0383(6) 0.7677(5) 0.1476(5) 0.020(2) Uani 1 d . . O4 O 0.0683(6) 0.7875(4) 0.2575(4) 0.042(2) Uani 1 d . . C4 C -0.0246(7) 0.8989(5) 0.1993(6) 0.032(2) Uani 1 d . . H4 H 0.0048(7) 0.9342(5) 0.2367(6) 0.038 Uiso 1 calc R . C9 C -0.2360(8) 0.6280(6) -0.0235(6) 0.032(2) Uani 1 d . . C7 C -0.1121(6) 0.7949(5) 0.0911(5) 0.020(2) Uani 1 d . . C8 C -0.1711(6) 0.7444(5) 0.0393(5) 0.021(2) Uani 1 d . . H8 H -0.2271(6) 0.7686(5) 0.0087(5) 0.026 Uiso 1 calc R . C5 C -0.0948(7) 0.9278(5) 0.1419(6) 0.033(2) Uani 1 d . . H5 H -0.1118(7) 0.9824(5) 0.1398(6) 0.040 Uiso 1 calc R . C10 C -0.2127(7) 0.5403(5) -0.0099(6) 0.032(2) Uani 1 d . . H10A H -0.2340(7) 0.5255(5) 0.0433(6) 0.038 Uiso 1 calc R . H10B H -0.2569(7) 0.5080(5) -0.0463(6) 0.038 Uiso 1 calc R . C6 C -0.1392(7) 0.8771(5) 0.0885(5) 0.032(2) Uani 1 d . . H6 H -0.1880(7) 0.8965(5) 0.0499(5) 0.038 Uiso 1 calc R . C13 C 0.2305(8) 0.6396(7) 0.2780(5) 0.043(3) Uani 1 d . . H13A H 0.1547(8) 0.6559(7) 0.2915(5) 0.065 Uiso 1 calc R 1 H13B H 0.2842(8) 0.6752(7) 0.3024(5) 0.065 Uiso 1 calc R 1 H13C H 0.2434(8) 0.5857(7) 0.2963(5) 0.065 Uiso 1 calc R 1 C14 C 0.3916(8) 0.6102(8) 0.1752(6) 0.055(3) Uani 1 d . . H14A H 0.4153(8) 0.6087(8) 0.1211(6) 0.082 Uiso 1 calc R 1 H14B H 0.3982(8) 0.5574(8) 0.1976(6) 0.082 Uiso 1 calc R 1 H14C H 0.4390(8) 0.6470(8) 0.2038(6) 0.082 Uiso 1 calc R 1 C11 C -0.3646(9) 0.6448(7) 0.0106(10) 0.097(7) Uani 1 d . . H11A H -0.4177(16) 0.6102(51) -0.0156(50) 0.146 Uiso 1 calc R . H11B H -0.3849(40) 0.6999(20) 0.0012(62) 0.146 Uiso 1 calc R . H11C H -0.3662(26) 0.6342(67) 0.0661(17) 0.146 Uiso 1 calc R . C3 C 0.1220(11) 0.8394(7) 0.3108(7) 0.063(4) Uani 1 d . . H3A H 0.1745(55) 0.8093(11) 0.3425(35) 0.095 Uiso 1 calc R . H3B H 0.0660(13) 0.8641(40) 0.3440(34) 0.095 Uiso 1 calc R . H3C H 0.1624(61) 0.8803(31) 0.2823(7) 0.095 Uiso 1 calc R . S1A S 0.2467(3) 0.6428(3) 0.1806(2) 0.0305(12) Uiso 0.568(7) d P 1 S1B S 0.2675(5) 0.5695(3) 0.2070(3) 0.035(2) Uiso 0.432(7) d P 2 O3A O -0.2404(18) 0.7274(13) -0.1216(13) 0.112(7) Uiso 0.568(7) d P 1 H3A H -0.2039(196) 0.7455(67) -0.1589(123) 0.168 Uiso 0.568(7) calc PR 1 O3B O -0.2508(62) 0.5889(47) -0.1612(52) 0.333(35) Uiso 0.432(7) d P 2 H3B H -0.2273(881) 0.5440(89) -0.1489(432) 0.499 Uiso 0.432(7) calc PR 2 C12 C -0.2062(11) 0.6483(8) -0.1069(7) 0.058(3) Uiso 1 d . . H12A H -0.1249(11) 0.6430(8) -0.1149(7) 0.069 Uiso 1 calc R 1 H12B H -0.2445(11) 0.6117(8) -0.1427(7) 0.069 Uiso 1 calc R 1 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 U1 0.0199(2) 0.0139(2) 0.0176(2) -0.00295(13) -0.00201(12) 0.00267(12) O1 0.037(3) 0.023(3) 0.024(3) -0.004(3) -0.015(3) 0.008(3) O2 0.014(3) 0.020(3) 0.032(3) -0.013(3) -0.001(3) 0.007(2) C2 0.019(4) 0.029(5) 0.031(5) -0.012(4) 0.003(4) 0.001(4) O5 0.052(4) 0.021(3) 0.024(3) 0.008(3) 0.004(3) 0.005(3) O6 0.021(3) 0.028(3) 0.034(4) 0.000(3) 0.001(3) -0.006(3) O7 0.042(4) 0.046(5) 0.060(5) -0.033(4) -0.029(4) 0.024(3) N1 0.020(3) 0.022(4) 0.030(4) -0.002(3) -0.007(3) 0.004(3) C1 0.013(4) 0.015(4) 0.030(4) -0.003(4) 0.003(3) 0.001(3) O4 0.052(4) 0.034(4) 0.039(4) -0.019(3) -0.022(3) 0.011(3) C4 0.032(5) 0.027(5) 0.037(5) -0.013(4) -0.001(4) -0.003(4) C9 0.031(5) 0.024(5) 0.042(6) -0.006(5) -0.013(4) 0.003(4) C7 0.015(4) 0.017(4) 0.027(5) 0.002(4) 0.000(3) 0.003(3) C8 0.023(4) 0.021(5) 0.020(4) -0.001(4) -0.001(3) 0.002(4) C5 0.032(5) 0.010(4) 0.057(6) -0.012(4) -0.003(5) 0.000(4) C10 0.025(5) 0.029(5) 0.041(6) -0.004(5) -0.008(4) 0.000(4) C6 0.029(5) 0.026(5) 0.040(6) 0.001(4) -0.008(4) 0.005(4) C13 0.041(6) 0.061(7) 0.027(5) -0.016(5) -0.008(5) 0.010(5) C14 0.033(6) 0.089(10) 0.042(6) -0.005(6) 0.002(5) 0.005(6) C11 0.033(6) 0.036(7) 0.223(19) -0.003(10) -0.092(10) -0.004(5) C3 0.070(8) 0.057(8) 0.063(8) -0.044(7) -0.034(7) 0.015(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U1 O6 1.776(6) . ? U1 O5 1.781(6) . ? U1 O1 2.255(6) . ? U1 O2 2.349(5) . ? U1 O2 2.351(5) 5_565 ? U1 O7 2.391(6) . ? U1 N1 2.589(7) . ? U1 U1 3.9167(7) 5_565 ? O1 C1 1.332(9) . ? O2 C10 1.425(10) . ? O2 U1 2.351(5) 5_565 ? C2 O4 1.358(11) . ? C2 C4 1.359(12) . ? C2 C1 1.409(12) . ? O7 S1A 1.489(8) . ? O7 S1B 1.492(8) . ? N1 C8 1.279(10) . ? N1 C9 1.500(11) . ? C1 C7 1.399(11) . ? O4 C3 1.430(11) . ? C4 C5 1.393(13) . ? C9 C12 1.53(2) . ? C9 C10 1.533(13) . ? C9 C11 1.68(2) . ? C7 C8 1.429(11) . ? C7 C6 1.433(12) . ? C5 C6 1.372(13) . ? C13 S1A 1.702(11) . ? C13 S1B 1.768(11) . ? C14 S1B 1.733(12) . ? C14 S1A 1.829(11) . ? O3A C12 1.43(2) . ? O3B C12 1.48(7) . ? 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 O6 U1 O5 178.7(3) . . ? O6 U1 O1 92.0(2) . . ? O5 U1 O1 87.0(3) . . ? O6 U1 O2 94.7(2) . . ? O5 U1 O2 86.6(3) . . ? O1 U1 O2 134.8(2) . . ? O6 U1 O2 90.1(2) . 5_565 ? O5 U1 O2 90.5(2) . 5_565 ? O1 U1 O2 157.6(2) . 5_565 ? O2 U1 O2 67.1(2) . 5_565 ? O6 U1 O7 88.4(3) . . ? O5 U1 O7 90.6(3) . . ? O1 U1 O7 80.7(2) . . ? O2 U1 O7 144.0(2) . . ? O2 U1 O7 77.0(2) 5_565 . ? O6 U1 N1 85.1(2) . . ? O5 U1 N1 95.3(3) . . ? O1 U1 N1 70.0(2) . . ? O2 U1 N1 66.2(2) . . ? O2 U1 N1 132.4(2) 5_565 . ? O7 U1 N1 149.8(2) . . ? O6 U1 U1 92.8(2) . 5_565 ? O5 U1 U1 88.3(2) . 5_565 ? O1 U1 U1 167.87(15) . 5_565 ? O2 U1 U1 33.58(12) . 5_565 ? O2 U1 U1 33.53(13) 5_565 5_565 ? O7 U1 U1 110.5(2) . 5_565 ? N1 U1 U1 99.3(2) . 5_565 ? C1 O1 U1 138.7(5) . . ? C10 O2 U1 112.4(5) . . ? C10 O2 U1 127.2(5) . 5_565 ? U1 O2 U1 112.9(2) . 5_565 ? O4 C2 C4 125.4(8) . . ? O4 C2 C1 113.9(7) . . ? C4 C2 C1 120.6(8) . . ? S1A O7 U1 127.0(4) . . ? S1B O7 U1 166.0(5) . . ? C8 N1 C9 118.1(7) . . ? C8 N1 U1 126.2(5) . . ? C9 N1 U1 114.7(5) . . ? O1 C1 C7 121.4(7) . . ? O1 C1 C2 119.5(7) . . ? C7 C1 C2 119.1(7) . . ? C2 O4 C3 117.0(7) . . ? C2 C4 C5 121.3(8) . . ? N1 C9 C12 108.8(8) . . ? N1 C9 C10 104.8(7) . . ? C12 C9 C10 108.7(9) . . ? N1 C9 C11 106.5(8) . . ? C12 C9 C11 120.7(9) . . ? C10 C9 C11 106.2(8) . . ? C1 C7 C8 123.8(7) . . ? C1 C7 C6 119.0(8) . . ? C8 C7 C6 116.8(7) . . ? N1 C8 C7 127.5(8) . . ? C6 C5 C4 119.8(8) . . ? O2 C10 C9 108.8(7) . . ? C5 C6 C7 120.1(8) . . ? O7 S1A C13 109.1(6) . . ? O7 S1A C14 104.5(5) . . ? C13 S1A C14 98.6(5) . . ? O7 S1B C14 109.1(6) . . ? O7 S1B C13 105.6(5) . . ? C14 S1B C13 99.8(6) . . ? O3A C12 C9 108.2(13) . . ? O3B C12 C9 111.4(42) . . ? _refine_diff_density_max 1.382 _refine_diff_density_min -1.323 _refine_diff_density_rms 0.185 data_3 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H19 Br N2 O7 U' _chemical_formula_weight 645.25 _chemical_melting_point ? _chemical_compound_source ? 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'U' 'U' -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 9.097(2) _cell_length_b 18.277(2) _cell_length_c 11.562(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.01(2) _cell_angle_gamma 90.00 _cell_volume 1817.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.358 _exptl_crystal_density_method ? _exptl_crystal_F_000 1200 _exptl_absorpt_coefficient_mu 11.167 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7254 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 4.10 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3698 _reflns_number_observed 2867 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0443P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3698 _refine_ls_number_parameters 234 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0360 _refine_ls_R_factor_obs 0.0294 _refine_ls_wR_factor_all 0.0705 _refine_ls_wR_factor_obs 0.0698 _refine_ls_goodness_of_fit_all 0.947 _refine_ls_goodness_of_fit_obs 1.075 _refine_ls_restrained_S_all 0.947 _refine_ls_restrained_S_obs 1.075 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group U1 U 0.03148(2) 0.467254(11) 0.35098(2) 0.03173(8) Uani 1 d . . O4 O -0.1070(5) 0.5318(2) 0.2657(4) 0.0517(11) Uani 1 d . . O5 O 0.2511(5) 0.5293(2) 0.3189(4) 0.0483(11) Uani 1 d . . O2 O -0.1080(4) 0.4475(2) 0.4855(3) 0.0342(8) Uani 1 d . . O3 O 0.1663(4) 0.4011(2) 0.4361(4) 0.0441(10) Uani 1 d . . O1 O 0.0453(6) 0.4175(3) 0.1790(4) 0.0659(15) Uani 1 d . . Br1 Br -0.27133(9) 0.23723(5) -0.26503(6) 0.0678(2) Uani 1 d . . N1 N -0.1715(5) 0.3618(2) 0.2824(4) 0.0331(10) Uani 1 d . . N2 N 0.4309(5) 0.5575(3) 0.2316(4) 0.0424(12) Uani 1 d . . C7 C -0.2111(7) 0.3240(3) 0.1821(5) 0.0380(13) Uani 1 d . . C12 C 0.3009(7) 0.5272(3) 0.2315(6) 0.0435(14) Uani 1 d . . H12 H 0.2422(73) 0.4991(36) 0.1542(58) 0.052 Uiso 1 d . . C6 C -0.1491(6) 0.3318(3) 0.0819(5) 0.0361(12) Uani 1 d . . C5 C -0.2194(7) 0.2889(3) -0.0224(5) 0.0428(14) Uani 1 d . . H5 H -0.2987(7) 0.2566(3) -0.0230(5) 0.051 Uiso 1 calc R . H7 H -0.2944(70) 0.2898(34) 0.1736(52) 0.051 Uiso 1 d . . C3 C -0.0538(7) 0.3407(3) -0.1245(5) 0.0445(14) Uani 1 d . . H3 H -0.0237(7) 0.3445(3) -0.1938(5) 0.053 Uiso 1 calc R . C9 C -0.1464(7) 0.3727(3) 0.4961(5) 0.0376(13) Uani 1 d . . H9A H -0.1981(7) 0.3680(3) 0.5570(5) 0.045 Uiso 1 calc R . H9B H -0.0523(7) 0.3435(3) 0.5220(5) 0.045 Uiso 1 calc R . C8 C -0.2538(6) 0.3455(3) 0.3718(4) 0.0322(12) Uani 1 d . . C1 C -0.0270(7) 0.3786(3) 0.0828(5) 0.0423(14) Uani 1 d . . C4 C -0.1723(7) 0.2943(3) -0.1232(5) 0.0418(14) Uani 1 d . . C2 C 0.0199(7) 0.3818(4) -0.0214(5) 0.049(2) Uani 1 d . . H2 H 0.1021(7) 0.4121(4) -0.0210(5) 0.059 Uiso 1 calc R . C11 C -0.4037(6) 0.3920(4) 0.3377(5) 0.0463(14) Uani 1 d . . H11A H -0.4471(6) 0.3892(4) 0.4039(5) 0.056 Uiso 1 calc R . H11B H -0.3770(6) 0.4427(4) 0.3298(5) 0.056 Uiso 1 calc R . C14 C 0.4824(8) 0.5546(5) 0.1257(6) 0.068(2) Uani 1 d . . H14A H 0.5799(8) 0.5798(5) 0.1434(6) 0.102 Uiso 1 calc R . H14B H 0.4064(8) 0.5777(5) 0.0576(6) 0.102 Uiso 1 calc R . H14C H 0.4951(8) 0.5045(5) 0.1059(6) 0.102 Uiso 1 calc R . C13 C 0.5327(7) 0.5918(5) 0.3408(6) 0.066(2) Uani 1 d . . H13A H 0.6223(7) 0.6111(5) 0.3247(6) 0.099 Uiso 1 calc R . H13B H 0.5652(7) 0.5563(5) 0.4053(6) 0.099 Uiso 1 calc R . H13C H 0.4784(7) 0.6309(5) 0.3650(6) 0.099 Uiso 1 calc R . O7 O -0.1642(5) 0.2203(2) 0.3967(5) 0.0558(12) Uani 1 d . . H7 H -0.1787(37) 0.1811(16) 0.4256(65) 0.084 Uiso 1 calc R . O6 O -0.5178(6) 0.3700(3) 0.2285(4) 0.0686(14) Uani 1 d . . H6 H -0.5701(73) 0.3370(37) 0.2431(14) 0.103 Uiso 1 calc R . C10 C -0.2956(7) 0.2660(3) 0.3791(5) 0.0405(13) Uani 1 d . . H10A H -0.3359(7) 0.2593(3) 0.4465(5) 0.049 Uiso 1 calc R . H10B H -0.3765(7) 0.2521(3) 0.3042(5) 0.049 Uiso 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 U1 0.02895(11) 0.03224(12) 0.03599(12) -0.00352(9) 0.01333(8) -0.00429(9) O4 0.040(2) 0.058(3) 0.056(3) 0.022(2) 0.014(2) 0.001(2) O5 0.042(2) 0.050(3) 0.062(3) -0.014(2) 0.029(2) -0.017(2) O2 0.038(2) 0.029(2) 0.039(2) -0.0045(15) 0.019(2) -0.007(2) O3 0.037(2) 0.034(2) 0.062(3) -0.007(2) 0.016(2) 0.003(2) O1 0.070(3) 0.086(4) 0.056(3) -0.037(2) 0.039(2) -0.046(3) Br1 0.0747(5) 0.0865(6) 0.0476(4) -0.0276(4) 0.0271(3) -0.0228(4) N1 0.029(2) 0.039(3) 0.033(2) 0.005(2) 0.013(2) -0.003(2) N2 0.030(3) 0.055(3) 0.047(3) 0.002(2) 0.019(2) 0.001(2) C7 0.036(3) 0.040(3) 0.040(3) -0.004(2) 0.015(2) -0.005(3) C12 0.033(3) 0.049(4) 0.049(3) -0.003(3) 0.013(3) 0.001(3) C6 0.037(3) 0.038(3) 0.033(3) -0.002(2) 0.011(2) -0.004(3) C5 0.043(3) 0.040(4) 0.047(3) -0.004(3) 0.018(3) -0.012(3) C3 0.050(4) 0.044(4) 0.041(3) -0.004(3) 0.017(3) 0.001(3) C9 0.045(3) 0.030(3) 0.043(3) -0.001(2) 0.021(3) -0.008(3) C8 0.034(3) 0.033(3) 0.033(3) 0.000(2) 0.016(2) -0.005(2) C1 0.046(4) 0.047(4) 0.038(3) -0.009(2) 0.019(3) -0.010(3) C4 0.047(4) 0.042(4) 0.036(3) -0.006(2) 0.013(3) 0.002(3) C2 0.049(4) 0.053(4) 0.054(4) -0.007(3) 0.029(3) -0.014(3) C11 0.035(3) 0.047(4) 0.060(4) 0.001(3) 0.019(3) -0.001(3) C14 0.052(4) 0.108(7) 0.054(4) 0.008(4) 0.031(4) 0.000(4) C13 0.048(4) 0.091(6) 0.065(4) -0.019(4) 0.026(3) -0.026(4) O7 0.044(3) 0.035(3) 0.095(3) 0.008(2) 0.033(2) 0.000(2) O6 0.043(3) 0.078(4) 0.072(3) -0.009(3) 0.000(2) -0.003(2) C10 0.042(3) 0.034(3) 0.052(3) -0.006(3) 0.025(3) -0.006(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 U1 O4 1.773(4) . ? U1 O3 1.775(4) . ? U1 O1 2.227(4) . ? U1 O2 2.333(4) . ? U1 O2 2.373(3) 3_566 ? U1 O5 2.428(4) . ? U1 N1 2.608(4) . ? U1 U1 3.8628(7) 3_566 ? O5 C12 1.235(7) . ? O2 C9 1.425(6) . ? O2 U1 2.373(3) 3_566 ? O1 C1 1.302(6) . ? Br1 C4 1.904(6) . ? N1 C7 1.296(7) . ? N1 C8 1.490(6) . ? N2 C12 1.305(8) . ? N2 C13 1.443(7) . ? N2 C14 1.448(8) . ? C7 C6 1.451(7) . ? C6 C1 1.400(8) . ? C6 C5 1.405(7) . ? C5 C4 1.370(8) . ? C3 C4 1.376(8) . ? C3 C2 1.384(8) . ? C9 C8 1.534(7) . ? C8 C10 1.511(7) . ? C8 C11 1.545(8) . ? C1 C2 1.404(8) . ? C11 O6 1.407(7) . ? O7 C10 1.417(7) . ? 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 O4 U1 O3 178.6(2) . . ? O4 U1 O1 90.7(2) . . ? O3 U1 O1 89.2(2) . . ? O4 U1 O2 91.8(2) . . ? O3 U1 O2 87.3(2) . . ? O1 U1 O2 137.14(14) . . ? O4 U1 O2 88.7(2) . 3_566 ? O3 U1 O2 92.0(2) . 3_566 ? O1 U1 O2 153.18(14) . 3_566 ? O2 U1 O2 69.67(14) . 3_566 ? O4 U1 O5 94.3(2) . . ? O3 U1 O5 87.0(2) . . ? O1 U1 O5 76.44(14) . . ? O2 U1 O5 145.82(13) . . ? O2 U1 O5 76.88(13) 3_566 . ? O4 U1 N1 91.1(2) . . ? O3 U1 N1 87.6(2) . . ? O1 U1 N1 70.56(14) . . ? O2 U1 N1 66.61(12) . . ? O2 U1 N1 136.25(13) 3_566 . ? O5 U1 N1 146.61(13) . . ? O4 U1 U1 90.3(2) . 3_566 ? O3 U1 U1 89.62(12) . 3_566 ? O1 U1 U1 172.29(11) . 3_566 ? O2 U1 U1 35.18(9) . 3_566 ? O2 U1 U1 34.49(9) 3_566 3_566 ? O5 U1 U1 111.11(10) . 3_566 ? N1 U1 U1 101.77(9) . 3_566 ? C12 O5 U1 130.5(4) . . ? C9 O2 U1 114.1(3) . . ? C9 O2 U1 125.3(3) . 3_566 ? U1 O2 U1 110.33(14) . 3_566 ? C1 O1 U1 145.6(4) . . ? C7 N1 C8 117.3(4) . . ? C7 N1 U1 128.9(4) . . ? C8 N1 U1 113.8(3) . . ? C12 N2 C13 120.6(5) . . ? C12 N2 C14 121.8(5) . . ? C13 N2 C14 117.6(5) . . ? N1 C7 C6 126.5(5) . . ? O5 C12 N2 124.0(6) . . ? C1 C6 C5 119.1(5) . . ? C1 C6 C7 124.6(5) . . ? C5 C6 C7 116.4(5) . . ? C4 C5 C6 120.6(5) . . ? C4 C3 C2 119.1(5) . . ? O2 C9 C8 109.3(4) . . ? N1 C8 C10 115.1(4) . . ? N1 C8 C9 105.9(4) . . ? C10 C8 C9 110.8(4) . . ? N1 C8 C11 108.3(4) . . ? C10 C8 C11 109.0(5) . . ? C9 C8 C11 107.5(5) . . ? O1 C1 C6 121.3(5) . . ? O1 C1 C2 120.0(5) . . ? C6 C1 C2 118.7(5) . . ? C5 C4 C3 121.1(5) . . ? C5 C4 Br1 120.1(5) . . ? C3 C4 Br1 118.7(4) . . ? C3 C2 C1 121.3(6) . . ? O6 C11 C8 113.8(5) . . ? O7 C10 C8 111.0(5) . . ? _refine_diff_density_max 1.613 _refine_diff_density_min -2.270 _refine_diff_density_rms 0.161 data_10 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H21 N O5 S U' _chemical_formula_weight 541.40 _chemical_melting_point ? _chemical_compound_source ? 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' 'N' 'N' 0.0061 0.0033 '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' 'U' 'U' -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.534(2) _cell_length_b 17.011(7) _cell_length_c 13.069(4) _cell_angle_alpha 90.00 _cell_angle_beta 97.11(2) _cell_angle_gamma 90.00 _cell_volume 1662.1(9) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.164 _exptl_crystal_density_method ? _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 9.910 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3158 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0392 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.39 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2917 _reflns_number_observed 2204 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1299P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2917 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_obs 0.0568 _refine_ls_wR_factor_all 0.1538 _refine_ls_wR_factor_obs 0.1440 _refine_ls_goodness_of_fit_all 0.956 _refine_ls_goodness_of_fit_obs 1.040 _refine_ls_restrained_S_all 0.956 _refine_ls_restrained_S_obs 1.040 _refine_ls_shift/esd_max -0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group U1 U 0.08393(5) 0.46048(2) 0.37129(3) 0.0178(2) Uani 1 d . . S1 S 0.5132(4) 0.3705(2) 0.3879(2) 0.0238(7) Uani 1 d . . O4 O 0.2484(11) 0.5352(5) 0.3786(7) 0.025(2) Uani 1 d . . O3 O -0.0763(10) 0.3830(5) 0.3623(6) 0.027(2) Uani 1 d . . O2 O -0.1126(11) 0.5477(5) 0.4457(6) 0.023(2) Uani 1 d . . O5 O 0.3165(10) 0.3629(5) 0.4037(6) 0.024(2) Uani 1 d . . O1 O 0.1464(10) 0.4320(6) 0.2129(6) 0.026(2) Uani 1 d . . N1 N -0.1683(14) 0.5248(6) 0.2372(8) 0.024(2) Uani 1 d . . H1 H -0.1543(14) 0.4817(6) 0.2746(8) 0.028 Uiso 1 calc R . C9 C -0.2630(16) 0.5813(8) 0.3863(10) 0.028(3) Uani 1 d . . H9A H -0.2966(16) 0.6302(8) 0.4201(10) 0.034 Uiso 1 calc R . H9B H -0.3650(16) 0.5444(8) 0.3840(10) 0.034 Uiso 1 calc R . C12 C 0.5317(16) 0.3121(9) 0.2763(11) 0.039(4) Uani 1 d . . H12A H 0.6553(35) 0.3136(49) 0.2601(48) 0.059 Uiso 1 calc R . H12B H 0.4515(101) 0.3329(36) 0.2178(21) 0.059 Uiso 1 calc R . H12C H 0.4985(129) 0.2577(15) 0.2895(28) 0.059 Uiso 1 calc R . C1 C 0.0374(15) 0.4001(8) 0.1326(9) 0.028(3) Uani 1 d . . C13 C 0.6233(17) 0.3072(9) 0.4839(11) 0.036(3) Uani 1 d . . H13A H 0.6066(109) 0.3271(33) 0.5524(11) 0.054 Uiso 1 calc R . H13B H 0.7513(27) 0.3053(44) 0.4771(48) 0.054 Uiso 1 calc R . H13C H 0.5726(89) 0.2542(16) 0.4751(47) 0.054 Uiso 1 calc R . C2 C 0.0674(17) 0.3275(8) 0.0935(10) 0.030(3) Uani 1 d . . H2 H 0.1667(17) 0.2974(8) 0.1234(10) 0.036 Uiso 1 calc R . C6 C -0.1084(19) 0.4459(9) 0.0890(10) 0.032(3) Uani 1 d . . C8 C -0.2293(19) 0.5999(8) 0.2781(10) 0.032(3) Uani 1 d . . C7 C -0.1325(23) 0.5280(9) 0.1272(10) 0.040(4) Uani 1 d . . H7A H -0.0232(23) 0.5592(9) 0.1218(10) 0.048 Uiso 1 calc R . H7B H -0.2339(23) 0.5537(9) 0.0845(10) 0.048 Uiso 1 calc R . C3 C -0.0445(18) 0.2972(9) 0.0110(10) 0.036(3) Uani 1 d . . H3 H -0.0206(18) 0.2472(9) -0.0169(10) 0.044 Uiso 1 calc R . C4 C -0.1926(18) 0.3406(10) -0.0306(11) 0.041(4) Uani 1 d . . H4 H -0.2728(18) 0.3190(10) -0.0852(11) 0.049 Uiso 1 calc R . C10 C -0.4117(20) 0.6238(11) 0.2190(11) 0.054(5) Uani 1 d . . H10A H -0.4520(82) 0.6730(40) 0.2475(64) 0.081 Uiso 1 calc R . H10B H -0.4997(46) 0.5824(35) 0.2260(80) 0.081 Uiso 1 calc R . H10C H -0.3990(42) 0.6313(72) 0.1459(20) 0.081 Uiso 1 calc R . C5 C -0.2247(18) 0.4145(10) 0.0063(11) 0.041(4) Uani 1 d . . H5 H -0.3247(18) 0.4441(10) -0.0238(11) 0.049 Uiso 1 calc R . C11 C -0.0909(21) 0.6645(8) 0.2754(11) 0.042(4) Uani 1 d . . H11A H -0.1321(64) 0.7121(20) 0.3074(69) 0.062 Uiso 1 calc R . H11B H -0.0740(99) 0.6756(41) 0.2036(12) 0.062 Uiso 1 calc R . H11C H 0.0229(42) 0.6473(24) 0.3134(66) 0.062 Uiso 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 U1 0.0064(3) 0.0303(3) 0.0159(3) -0.0008(2) -0.0013(2) 0.0009(2) S1 0.0092(13) 0.035(2) 0.026(2) -0.0039(13) -0.0019(11) 0.0017(12) O4 0.012(4) 0.031(5) 0.030(5) -0.007(4) -0.004(3) 0.000(3) O3 0.016(4) 0.035(5) 0.027(5) 0.002(4) -0.003(3) 0.004(4) O2 0.015(4) 0.033(5) 0.021(5) -0.003(4) -0.002(3) 0.010(3) O5 0.009(4) 0.040(5) 0.024(4) -0.003(4) 0.000(3) 0.005(3) O1 0.014(4) 0.046(5) 0.018(4) -0.012(4) 0.001(3) -0.001(4) N1 0.029(6) 0.024(6) 0.016(5) 0.001(4) -0.005(4) 0.011(4) C9 0.011(6) 0.044(8) 0.027(7) 0.000(6) -0.008(5) 0.008(6) C12 0.007(6) 0.070(11) 0.042(8) -0.021(8) 0.007(5) -0.005(6) C1 0.015(6) 0.052(8) 0.016(6) 0.002(6) -0.001(5) 0.007(5) C13 0.019(6) 0.047(8) 0.041(8) 0.002(7) -0.005(6) 0.015(6) C2 0.023(6) 0.044(8) 0.022(6) -0.002(6) -0.001(5) 0.004(6) C6 0.029(7) 0.050(9) 0.018(7) -0.004(6) 0.004(5) 0.003(6) C8 0.047(8) 0.028(7) 0.019(6) -0.001(5) -0.005(6) 0.015(6) C7 0.050(9) 0.052(10) 0.018(7) 0.001(6) 0.001(6) 0.010(7) C3 0.031(7) 0.054(9) 0.025(7) -0.010(7) 0.004(6) -0.010(7) C4 0.020(7) 0.070(11) 0.030(8) -0.007(7) 0.000(6) -0.002(7) C10 0.044(9) 0.088(13) 0.025(8) -0.002(8) -0.011(6) 0.044(9) C5 0.017(7) 0.073(11) 0.029(8) -0.009(8) -0.011(5) 0.004(7) C11 0.059(10) 0.032(7) 0.035(8) 0.004(6) 0.007(7) 0.011(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U1 O4 1.769(8) . ? U1 O3 1.781(9) . ? U1 O1 2.233(8) . ? U1 O2 2.379(8) 3_566 ? U1 O2 2.387(8) . ? U1 O5 2.412(8) . ? U1 N1 2.656(10) . ? U1 U1 3.9723(12) 3_566 ? S1 O5 1.527(8) . ? S1 C13 1.778(13) . ? S1 C12 1.785(13) . ? O2 C9 1.412(13) . ? O2 U1 2.379(8) 3_566 ? O1 C1 1.362(14) . ? N1 C8 1.48(2) . ? N1 C7 1.50(2) . ? C9 C8 1.50(2) . ? C1 C2 1.37(2) . ? C1 C6 1.41(2) . ? C2 C3 1.38(2) . ? C6 C5 1.41(2) . ? C6 C7 1.50(2) . ? C8 C11 1.52(2) . ? C8 C10 1.55(2) . ? C3 C4 1.39(2) . ? C4 C5 1.38(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 U1 O3 178.0(4) . . ? O4 U1 O1 88.8(4) . . ? O3 U1 O1 89.8(4) . . ? O4 U1 O2 90.7(4) . 3_566 ? O3 U1 O2 90.0(3) . 3_566 ? O1 U1 O2 156.4(3) . 3_566 ? O4 U1 O2 89.8(3) . . ? O3 U1 O2 92.1(3) . . ? O1 U1 O2 136.5(3) . . ? O2 U1 O2 67.1(3) 3_566 . ? O4 U1 O5 89.8(3) . . ? O3 U1 O5 88.5(3) . . ? O1 U1 O5 77.4(3) . . ? O2 U1 O5 79.0(3) 3_566 . ? O2 U1 O5 146.1(3) . . ? O4 U1 N1 100.3(4) . . ? O3 U1 N1 80.6(3) . . ? O1 U1 N1 72.1(3) . . ? O2 U1 N1 131.0(3) 3_566 . ? O2 U1 N1 65.4(3) . . ? O5 U1 N1 147.6(3) . . ? O4 U1 U1 90.3(3) . 3_566 ? O3 U1 U1 91.3(3) . 3_566 ? O1 U1 U1 170.0(2) . 3_566 ? O2 U1 U1 33.6(2) 3_566 3_566 ? O2 U1 U1 33.5(2) . 3_566 ? O5 U1 U1 112.6(2) . 3_566 ? N1 U1 U1 98.2(2) . 3_566 ? O5 S1 C13 103.3(6) . . ? O5 S1 C12 103.8(5) . . ? C13 S1 C12 99.4(7) . . ? C9 O2 U1 122.9(7) . 3_566 ? C9 O2 U1 121.6(7) . . ? U1 O2 U1 112.9(3) 3_566 . ? S1 O5 U1 127.9(5) . . ? C1 O1 U1 128.7(7) . . ? C8 N1 C7 114.6(10) . . ? C8 N1 U1 110.3(7) . . ? C7 N1 U1 116.7(8) . . ? O2 C9 C8 112.6(10) . . ? O1 C1 C2 122.4(11) . . ? O1 C1 C6 117.2(12) . . ? C2 C1 C6 120.4(12) . . ? C1 C2 C3 121.0(12) . . ? C1 C6 C5 118.7(13) . . ? C1 C6 C7 120.0(13) . . ? C5 C6 C7 121.2(13) . . ? N1 C8 C9 104.7(10) . . ? N1 C8 C11 111.8(12) . . ? C9 C8 C11 111.8(11) . . ? N1 C8 C10 110.1(11) . . ? C9 C8 C10 106.4(12) . . ? C11 C8 C10 111.6(12) . . ? N1 C7 C6 109.2(11) . . ? C2 C3 C4 119.2(13) . . ? C5 C4 C3 121.0(13) . . ? C4 C5 C6 119.6(13) . . ? _refine_diff_density_max 3.069 _refine_diff_density_min -5.320 _refine_diff_density_rms 0.375 data_6. _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C17 H25 Br N3 O7 U' _chemical_formula_weight 701.34 _chemical_melting_point ? _chemical_compound_source ? 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' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'U' 'U' -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? 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 8.142(2) _cell_length_b 25.595(5) _cell_length_c 10.927(2) _cell_angle_alpha 90.000(14) _cell_angle_beta 107.86(2) _cell_angle_gamma 90.00(2) _cell_volume 2167.5(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.149 _exptl_crystal_density_method ? _exptl_crystal_F_000 1324 _exptl_absorpt_coefficient_mu 9.374 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4093 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 24.97 _reflns_number_total 3812 _reflns_number_observed 3103 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+19.2521P] 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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3812 _refine_ls_number_parameters 269 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_obs 0.0486 _refine_ls_wR_factor_all 0.1308 _refine_ls_wR_factor_obs 0.1254 _refine_ls_goodness_of_fit_all 1.077 _refine_ls_goodness_of_fit_obs 1.153 _refine_ls_restrained_S_all 1.077 _refine_ls_restrained_S_obs 1.153 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group U1 U 0.45891(5) 0.47584(2) 0.15727(3) 0.0207(2) Uani 1 d . . O3 O 0.2972(9) 0.4324(3) 0.0635(7) 0.029(2) Uani 1 d . . O5 O 0.2419(9) 0.5283(3) 0.2106(7) 0.028(2) Uani 1 d . . O4 O 0.6238(10) 0.5171(3) 0.2533(8) 0.038(2) Uani 1 d . . N1 N 0.6749(10) 0.3986(3) 0.2226(7) 0.020(2) Uani 1 d . . N2 N 0.0713(11) 0.5624(4) 0.3197(8) 0.025(2) Uani 1 d . . O1 O 0.4250(12) 0.4346(4) 0.3308(8) 0.060(3) Uani 1 d . . C6 C 0.6240(12) 0.3682(4) 0.4214(9) 0.021(2) Uani 1 d . . C7 C 0.7026(13) 0.3670(4) 0.3177(9) 0.022(2) Uani 1 d . . H7 H 0.7814(13) 0.3403(4) 0.3212(9) 0.026 Uiso 1 calc R . C5 C 0.6901(14) 0.3332(5) 0.5226(10) 0.027(2) Uani 1 d . . H5 H 0.7777(14) 0.3102(5) 0.5208(10) 0.033 Uiso 1 calc R . C12 C 0.1978(14) 0.5334(4) 0.3107(10) 0.024(2) Uani 1 d . . H12 H 0.2603(14) 0.5150(4) 0.3835(10) 0.029 Uiso 1 calc R . O2 O 0.6101(10) 0.4613(3) 0.0093(7) 0.026(2) Uani 1 d . . C1 C 0.4921(14) 0.4030(5) 0.4261(9) 0.029(2) Uani 1 d . . C3 C 0.4998(14) 0.3673(5) 0.6330(10) 0.029(2) Uani 1 d . . H3 H 0.4621(14) 0.3680(5) 0.7052(10) 0.034 Uiso 1 calc R . C9 C 0.6613(15) 0.4073(5) 0.0001(10) 0.031(3) Uani 1 d . . H9A H 0.7217(15) 0.4042(5) -0.0635(10) 0.038 Uiso 1 calc R . H9B H 0.5604(15) 0.3849(5) -0.0253(10) 0.038 Uiso 1 calc R . C2 C 0.4299(15) 0.4011(5) 0.5320(10) 0.034(3) Uani 1 d . . H2 H 0.3398(15) 0.4230(5) 0.5343(10) 0.041 Uiso 1 calc R . C13 C -0.0329(15) 0.5928(5) 0.2112(11) 0.037(3) Uani 1 d . . H13A H -0.1195(15) 0.6116(5) 0.2361(11) 0.056 Uiso 1 calc R . H13B H -0.0874(15) 0.5697(5) 0.1412(11) 0.056 Uiso 1 calc R . H13C H 0.0395(15) 0.6170(5) 0.1847(11) 0.056 Uiso 1 calc R . C4 C 0.6247(16) 0.3329(4) 0.6260(10) 0.030(3) Uani 1 d . . C10 C 0.9327(14) 0.4266(6) 0.1735(11) 0.039(3) Uani 1 d . . H10A H 0.9916(14) 0.4267(6) 0.1086(11) 0.047 Uiso 1 calc R 1 H10B H 0.8948(14) 0.4620(6) 0.1817(11) 0.047 Uiso 1 calc R 1 O6A O 1.0456(13) 0.4109(5) 0.2892(10) 0.053(3) Uani 0.80 d P 1 H6A H 1.1419(18) 0.4225(13) 0.2966(19) 0.080 Uiso 0.80 calc PR 1 O6B O 0.9622(35) 0.3134(5) 0.2189(17) 0.043(11) Uani 0.20 d PR 2 H6B H 1.0305(36) 0.3365(5) 0.2535(16) 0.064 Uiso 0.20 calc PR 2 C11 C 0.8310(16) 0.3345(5) 0.1172(11) 0.039(3) Uani 1 d . . H11A H 0.7294(16) 0.3127(5) 0.1034(11) 0.047 Uiso 1 calc R 2 H11B H 0.8663(16) 0.3322(5) 0.0402(11) 0.047 Uiso 1 calc R 2 C8 C 0.7788(13) 0.3913(5) 0.1315(9) 0.026(2) Uani 1 d . . C14 C 0.0188(15) 0.5637(5) 0.4352(11) 0.036(3) Uani 1 d . . H14A H -0.0764(15) 0.5874(5) 0.4228(11) 0.054 Uiso 1 calc R . H14B H 0.1137(15) 0.5753(5) 0.5063(11) 0.054 Uiso 1 calc R . H14C H -0.0156(15) 0.5294(5) 0.4527(11) 0.054 Uiso 1 calc R . Br1 Br 0.7205(2) 0.28676(5) 0.76636(12) 0.0460(4) Uani 1 d . . N3 N 0.2445(13) 0.2420(5) 0.4827(11) 0.048(3) Uani 1 d . . C15 C 0.1528(25) 0.2823(8) 0.4952(23) 0.094(8) Uani 1 d . . H15 H 0.1486(25) 0.3106(8) 0.4409(23) 0.112 Uiso 1 calc R . C16 C 0.3358(32) 0.2427(10) 0.3874(19) 0.106(8) Uani 1 d . . H16A H 0.3965(32) 0.2103(10) 0.3908(19) 0.159 Uiso 1 calc R . H16B H 0.4166(32) 0.2711(10) 0.4052(19) 0.159 Uiso 1 calc R . H16C H 0.2546(32) 0.2471(10) 0.3034(19) 0.159 Uiso 1 calc R . C17 C 0.2680(25) 0.1957(6) 0.5592(18) 0.074(5) Uani 1 d . . H17A H 0.3405(25) 0.1717(6) 0.5319(18) 0.111 Uiso 1 calc R . H17B H 0.1579(25) 0.1797(6) 0.5492(18) 0.111 Uiso 1 calc R . H17C H 0.3214(25) 0.2045(6) 0.6479(18) 0.111 Uiso 1 calc R . O7 O 0.0719(21) 0.2860(9) 0.5724(21) 0.149(9) Uani 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 U1 0.0172(2) 0.0304(2) 0.0173(2) -0.0007(2) 0.00926(14) 0.0027(2) O3 0.020(4) 0.032(4) 0.033(4) -0.002(3) 0.008(3) -0.002(3) O5 0.022(4) 0.039(5) 0.026(4) -0.003(3) 0.011(3) 0.007(3) O4 0.019(4) 0.052(6) 0.039(4) -0.025(4) 0.004(3) -0.003(4) N1 0.018(4) 0.027(5) 0.019(4) 0.002(3) 0.010(3) 0.005(4) N2 0.021(4) 0.041(6) 0.018(4) -0.009(4) 0.012(3) -0.006(4) O1 0.060(6) 0.085(8) 0.047(5) 0.046(5) 0.037(5) 0.068(6) C6 0.017(5) 0.024(6) 0.024(5) -0.003(4) 0.009(4) -0.001(4) C7 0.019(5) 0.026(6) 0.021(5) -0.001(4) 0.007(4) 0.002(4) C5 0.025(6) 0.038(6) 0.025(5) 0.003(5) 0.016(4) 0.000(5) C12 0.025(6) 0.026(6) 0.024(5) 0.003(4) 0.011(4) 0.001(4) O2 0.028(4) 0.028(4) 0.030(4) 0.000(3) 0.019(3) 0.003(3) C1 0.023(5) 0.047(7) 0.019(5) 0.004(5) 0.012(4) 0.005(5) C3 0.031(6) 0.039(7) 0.021(5) 0.006(5) 0.015(5) 0.002(5) C9 0.027(6) 0.046(7) 0.025(5) -0.006(5) 0.015(5) -0.005(5) C2 0.033(6) 0.046(7) 0.032(6) 0.001(5) 0.023(5) 0.015(6) C13 0.024(6) 0.053(8) 0.035(6) 0.003(6) 0.010(5) 0.010(6) C4 0.048(7) 0.028(6) 0.019(5) -0.003(4) 0.018(5) -0.008(5) C10 0.027(6) 0.056(8) 0.038(6) 0.006(6) 0.016(5) -0.002(6) O6A 0.024(6) 0.101(11) 0.037(6) 0.018(6) 0.012(5) -0.003(6) O6B 0.032(23) 0.060(30) 0.041(23) -0.002(21) 0.018(19) 0.031(22) C11 0.039(7) 0.049(8) 0.035(6) 0.000(6) 0.022(5) 0.020(6) C8 0.021(5) 0.042(7) 0.021(5) 0.002(5) 0.013(4) 0.007(5) C14 0.027(6) 0.051(8) 0.039(6) -0.012(6) 0.022(5) -0.007(6) Br1 0.0738(9) 0.0408(7) 0.0320(6) 0.0126(5) 0.0288(6) 0.0169(7) N3 0.023(5) 0.055(8) 0.061(7) -0.011(6) 0.007(5) 0.005(5) C15 0.055(12) 0.064(13) 0.120(18) -0.009(11) -0.036(12) 0.018(10) C16 0.125(20) 0.131(21) 0.070(13) -0.005(13) 0.042(13) -0.029(17) C17 0.088(14) 0.036(9) 0.102(14) -0.002(9) 0.035(11) 0.003(9) O7 0.072(10) 0.182(20) 0.201(20) -0.050(15) 0.053(13) 0.051(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag U1 O4 1.777(8) . ? U1 O3 1.787(7) . ? U1 O1 2.259(8) . ? U1 O2 2.343(7) . ? U1 O2 2.365(7) 3_665 ? U1 O5 2.429(7) . ? U1 N1 2.596(8) . ? U1 U1 3.8989(9) 3_665 ? O5 C12 1.258(12) . ? N1 C7 1.282(13) . ? N1 C8 1.502(11) . ? N2 C12 1.298(14) . ? N2 C14 1.451(13) . ? N2 C13 1.454(14) . ? O1 C1 1.299(13) . ? C6 C5 1.396(15) . ? C6 C1 1.410(15) . ? C6 C7 1.462(13) . ? C5 C4 1.389(13) . ? O2 C9 1.456(14) . ? O2 U1 2.365(7) 3_665 ? C1 C2 1.399(14) . ? C3 C4 1.37(2) . ? C3 C2 1.38(2) . ? C9 C8 1.517(15) . ? C4 Br1 1.902(11) . ? C10 O6A 1.38(2) . ? C10 C8 1.50(2) . ? O6B C11 1.39(2) . ? C11 C8 1.54(2) . ? N3 C15 1.30(2) . ? N3 C17 1.43(2) . ? N3 C16 1.45(2) . ? C15 O7 1.22(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 U1 O3 178.0(4) . . ? O4 U1 O1 92.7(4) . . ? O3 U1 O1 86.1(4) . . ? O4 U1 O2 92.3(3) . . ? O3 U1 O2 87.5(3) . . ? O1 U1 O2 136.9(3) . . ? O4 U1 O2 90.5(4) . 3_665 ? O3 U1 O2 91.3(3) . 3_665 ? O1 U1 O2 154.5(3) . 3_665 ? O2 U1 O2 68.2(3) . 3_665 ? O4 U1 O5 90.2(3) . . ? O3 U1 O5 91.1(3) . . ? O1 U1 O5 76.8(3) . . ? O2 U1 O5 145.9(3) . . ? O2 U1 O5 77.8(2) 3_665 . ? O4 U1 N1 88.0(3) . . ? O3 U1 N1 90.1(3) . . ? O1 U1 N1 70.2(3) . . ? O2 U1 N1 67.3(2) . . ? O2 U1 N1 135.3(2) 3_665 . ? O5 U1 N1 146.8(2) . . ? O4 U1 U1 91.7(3) . 3_665 ? O3 U1 U1 89.3(2) . 3_665 ? O1 U1 U1 170.4(2) . 3_665 ? O2 U1 U1 34.3(2) . 3_665 ? O2 U1 U1 33.9(2) 3_665 3_665 ? O5 U1 U1 111.7(2) . 3_665 ? N1 U1 U1 101.5(2) . 3_665 ? C12 O5 U1 133.5(7) . . ? C7 N1 C8 117.6(8) . . ? C7 N1 U1 129.8(6) . . ? C8 N1 U1 112.6(6) . . ? C12 N2 C14 122.1(10) . . ? C12 N2 C13 121.5(9) . . ? C14 N2 C13 116.3(9) . . ? C1 O1 U1 146.5(7) . . ? C5 C6 C1 119.3(9) . . ? C5 C6 C7 116.5(9) . . ? C1 C6 C7 124.1(9) . . ? N1 C7 C6 127.2(9) . . ? C4 C5 C6 119.9(10) . . ? O5 C12 N2 124.7(10) . . ? C9 O2 U1 114.9(5) . . ? C9 O2 U1 126.8(6) . 3_665 ? U1 O2 U1 111.8(3) . 3_665 ? O1 C1 C2 121.0(10) . . ? O1 C1 C6 120.2(9) . . ? C2 C1 C6 118.7(10) . . ? C4 C3 C2 119.4(9) . . ? O2 C9 C8 107.6(9) . . ? C3 C2 C1 121.3(10) . . ? C3 C4 C5 121.3(10) . . ? C3 C4 Br1 118.9(7) . . ? C5 C4 Br1 119.7(9) . . ? O6A C10 C8 111.4(11) . . ? O6B C11 C8 117.0(12) . . ? C10 C8 N1 108.1(9) . . ? C10 C8 C9 110.6(9) . . ? N1 C8 C9 105.9(8) . . ? C10 C8 C11 111.8(10) . . ? N1 C8 C11 114.5(9) . . ? C9 C8 C11 105.8(9) . . ? C15 N3 C17 124.9(17) . . ? C15 N3 C16 120.0(19) . . ? C17 N3 C16 115.0(15) . . ? O7 C15 N3 125.4(23) . . ? _refine_diff_density_max 1.940 _refine_diff_density_min -3.397 _refine_diff_density_rms 0.249 data_1.H2O. _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C18 H24 N O7.50 S1.50 U' _chemical_formula_weight 660.50 _chemical_melting_point ? _chemical_compound_source ? 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' 'U' 'U' -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 7.6825(15) _cell_length_b 17.995(3) _cell_length_c 32.276(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4462.0(13) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.966 _exptl_crystal_density_method ? _exptl_crystal_F_000 2520 _exptl_absorpt_coefficient_mu 7.456 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4063 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0553 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -1 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 24.96 _reflns_number_total 3914 _reflns_number_observed 2469 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1043P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3914 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0937 _refine_ls_R_factor_obs 0.0506 _refine_ls_wR_factor_all 0.1713 _refine_ls_wR_factor_obs 0.1497 _refine_ls_goodness_of_fit_all 1.104 _refine_ls_goodness_of_fit_obs 1.237 _refine_ls_restrained_S_all 1.104 _refine_ls_restrained_S_obs 1.237 _refine_ls_shift/esd_max -8.605 _refine_ls_shift/esd_mean 0.159 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group U1 U 0.62340(6) 0.43011(2) 0.535987(14) 0.0224(2) Uani 1 d . . S1 S 1.0475(5) 0.3653(2) 0.50590(13) 0.0336(9) Uani 1 d . . O2 O 0.4115(13) 0.5245(5) 0.5315(3) 0.034(2) Uani 1 d . . O5 O 0.8480(11) 0.3616(5) 0.5023(3) 0.031(2) Uani 1 d . . O1 O 0.7422(12) 0.3674(5) 0.5912(3) 0.031(2) Uani 1 d . . O4 O 0.4792(12) 0.3550(5) 0.5224(3) 0.029(2) Uani 1 d . . O3 O 0.7736(12) 0.5010(5) 0.5499(3) 0.034(2) Uani 1 d . . C16 C 1.1249(19) 0.3258(8) 0.4592(5) 0.045(4) Uani 1 d . . H16A H 1.1072(19) 0.3602(8) 0.4369(5) 0.068 Uiso 1 calc R . H16B H 1.0627(19) 0.2806(8) 0.4536(5) 0.068 Uiso 1 calc R . H16C H 1.2468(19) 0.3151(8) 0.4619(5) 0.068 Uiso 1 calc R . O7 O 0.0640(14) 0.4359(6) 0.6153(4) 0.049(3) Uani 1 d . . H7 H -0.0382(70) 0.4309(69) 0.6085(42) 0.074 Uiso 1 calc R . N1 N 0.4348(14) 0.4435(5) 0.5995(4) 0.028(3) Uani 1 d . . C17 C 1.0979(16) 0.2905(9) 0.5394(4) 0.034(3) Uani 1 d . . H17A H 1.0632(16) 0.3029(9) 0.5672(4) 0.051 Uiso 1 calc R . H17B H 1.2210(16) 0.2813(9) 0.5388(4) 0.051 Uiso 1 calc R . H17C H 1.0370(16) 0.2467(9) 0.5305(4) 0.051 Uiso 1 calc R . C13 C 0.4005(20) 0.5643(8) 0.5695(6) 0.048(4) Uani 1 d . . H13A H 0.3276(20) 0.6079(8) 0.5660(6) 0.057 Uiso 1 calc R . H13B H 0.5155(20) 0.5806(8) 0.5780(6) 0.057 Uiso 1 calc R . C11 C 0.4118(15) 0.3946(7) 0.6277(4) 0.024(3) Uani 1 d . . H11 H 0.3247(15) 0.4036(7) 0.6471(4) 0.029 Uiso 1 calc R . O6 O 0.4872(17) 0.5554(8) 0.6609(5) 0.076(5) Uani 1 d . . H6 H 0.5621(23) 0.5409(128) 0.6447(32) 0.114 Uiso 1 calc R . C4 C 0.5498(20) 0.2113(8) 0.6727(4) 0.033(3) Uani 1 d . . C1 C 0.6778(17) 0.3184(7) 0.6164(4) 0.026(3) Uani 1 d . . C12 C 0.3207(16) 0.5121(7) 0.6033(5) 0.027(3) Uani 1 d . . C8 C 0.2689(20) 0.2691(7) 0.6749(5) 0.039(4) Uani 1 d . . H8 H 0.1917(20) 0.3052(7) 0.6657(5) 0.046 Uiso 1 calc R . C2 C 0.7810(20) 0.2578(8) 0.6290(4) 0.037(4) Uani 1 d . . H2 H 0.8918(20) 0.2520(8) 0.6178(4) 0.044 Uiso 1 calc R . C6 C 0.3221(25) 0.1616(9) 0.7172(5) 0.053(5) Uani 1 d . . H6 H 0.2826(25) 0.1276(9) 0.7368(5) 0.064 Uiso 1 calc R . C10 C 0.5104(18) 0.3261(7) 0.6321(4) 0.025(3) Uani 1 d . . C7 C 0.2123(25) 0.2177(9) 0.7024(6) 0.055(5) Uani 1 d . . H7 H 0.0978(25) 0.2198(9) 0.7116(6) 0.065 Uiso 1 calc R . C14 C 0.1412(23) 0.4952(11) 0.5917(9) 0.101(10) Uani 1 d . . H14A H 0.0712(23) 0.5397(11) 0.5951(9) 0.122 Uiso 1 calc R . H14B H 0.1385(23) 0.4819(11) 0.5625(9) 0.122 Uiso 1 calc R . C5 C 0.4827(26) 0.1577(8) 0.7028(5) 0.052(5) Uani 1 d . . H5 H 0.5552(26) 0.1198(8) 0.7120(5) 0.062 Uiso 1 calc R . C9 C 0.4422(18) 0.2697(7) 0.6599(5) 0.034(4) Uani 1 d . . C3 C 0.7222(21) 0.2079(8) 0.6569(5) 0.047(4) Uani 1 d . . H3 H 0.7962(21) 0.1703(8) 0.6659(5) 0.056 Uiso 1 calc R . C15 C 0.3313(33) 0.5455(13) 0.6443(10) 0.132(14) Uani 1 d . . H15A H 0.2745(33) 0.5936(13) 0.6430(10) 0.158 Uiso 1 calc R . H15B H 0.2639(33) 0.5149(13) 0.6631(10) 0.158 Uiso 1 calc R . O1W O 0.1360(20) 0.5641(8) 0.2489(5) 0.094(5) Uiso 1 d . . H1W1 H 0.0520(135) 0.5014(53) 0.2297(31) 0.000(25) Uiso 1 d . . H1W2 H 0.2139(128) 0.5458(54) 0.2896(29) 0.000(24) Uiso 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 U1 0.0180(3) 0.0151(3) 0.0342(3) 0.0004(2) 0.0037(2) 0.0002(2) S1 0.021(2) 0.020(2) 0.060(3) -0.003(2) 0.007(2) -0.0015(14) O2 0.049(7) 0.022(5) 0.032(6) 0.004(4) -0.003(5) 0.017(5) O5 0.020(5) 0.034(5) 0.039(5) 0.004(4) 0.004(4) 0.011(4) O1 0.020(5) 0.027(5) 0.046(6) 0.004(4) -0.003(5) 0.002(4) O4 0.033(6) 0.021(5) 0.032(5) -0.004(4) 0.005(4) 0.004(4) O3 0.020(5) 0.024(5) 0.057(6) -0.005(5) 0.006(5) -0.007(4) C16 0.020(7) 0.033(8) 0.083(13) -0.001(8) -0.001(9) 0.004(7) O7 0.024(5) 0.055(7) 0.068(8) 0.008(6) -0.007(5) -0.009(5) N1 0.021(6) 0.013(5) 0.049(8) -0.004(5) -0.003(5) 0.006(4) C17 0.014(7) 0.042(8) 0.046(9) -0.012(7) -0.001(6) -0.001(6) C13 0.037(10) 0.036(8) 0.070(12) -0.002(8) 0.010(9) 0.010(7) C11 0.015(7) 0.026(7) 0.031(7) -0.004(6) -0.008(6) 0.001(5) O6 0.053(9) 0.052(8) 0.124(13) -0.041(9) -0.020(8) 0.004(7) C4 0.047(9) 0.030(7) 0.023(7) 0.004(6) -0.011(7) -0.007(7) C1 0.022(7) 0.024(7) 0.031(8) -0.009(6) -0.009(6) -0.003(5) C12 0.021(6) 0.024(7) 0.037(8) 0.005(6) 0.003(6) 0.015(6) C8 0.044(9) 0.026(8) 0.046(9) 0.007(7) -0.013(8) 0.001(7) C2 0.041(9) 0.032(8) 0.037(9) -0.003(7) -0.007(7) 0.012(7) C6 0.067(12) 0.044(10) 0.049(11) 0.020(8) -0.003(9) -0.027(9) C10 0.034(8) 0.019(6) 0.023(7) -0.001(5) 0.003(6) 0.001(6) C7 0.062(11) 0.034(9) 0.067(12) 0.008(8) 0.011(10) -0.020(9) C14 0.032(10) 0.053(12) 0.219(31) -0.028(16) -0.048(15) 0.008(10) C5 0.071(13) 0.027(9) 0.058(11) 0.012(8) -0.037(10) -0.005(8) C9 0.025(7) 0.022(7) 0.055(10) -0.001(6) -0.005(7) -0.010(6) C3 0.043(10) 0.026(8) 0.071(12) 0.009(8) -0.013(9) 0.005(8) C15 0.110(22) 0.084(17) 0.202(34) -0.099(21) -0.092(22) 0.051(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 U1 O3 1.778(9) . ? U1 O4 1.802(9) . ? U1 O1 2.298(9) . ? U1 O2 2.341(9) 5_666 ? U1 O2 2.358(9) . ? U1 O5 2.382(8) . ? U1 N1 2.521(12) . ? U1 U1 3.9139(10) 5_666 ? S1 O5 1.538(9) . ? S1 C16 1.77(2) . ? S1 C17 1.77(2) . ? O2 C13 1.42(2) . ? O2 U1 2.341(9) 5_666 ? O1 C1 1.30(2) . ? O7 C14 1.44(3) . ? N1 C11 1.28(2) . ? N1 C12 1.519(15) . ? C13 C12 1.57(2) . ? C11 C10 1.45(2) . ? O6 C15 1.33(2) . ? C4 C9 1.40(2) . ? C4 C3 1.42(2) . ? C4 C5 1.46(2) . ? C1 C10 1.39(2) . ? C1 C2 1.41(2) . ? C12 C15 1.45(3) . ? C12 C14 1.46(2) . ? C8 C7 1.35(2) . ? C8 C9 1.42(2) . ? C2 C3 1.35(2) . ? C6 C5 1.32(3) . ? C6 C7 1.40(2) . ? C10 C9 1.45(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 U1 O4 177.3(4) . . ? O3 U1 O1 84.2(4) . . ? O4 U1 O1 93.7(4) . . ? O3 U1 O2 93.4(4) . 5_666 ? O4 U1 O2 87.9(4) . 5_666 ? O1 U1 O2 159.7(3) . 5_666 ? O3 U1 O2 86.9(4) . . ? O4 U1 O2 95.8(4) . . ? O1 U1 O2 132.5(3) . . ? O2 U1 O2 67.2(4) 5_666 . ? O3 U1 O5 90.9(4) . . ? O4 U1 O5 86.9(3) . . ? O1 U1 O5 79.1(3) . . ? O2 U1 O5 80.7(3) 5_666 . ? O2 U1 O5 147.7(3) . . ? O3 U1 N1 95.7(4) . . ? O4 U1 N1 85.2(4) . . ? O1 U1 N1 69.2(3) . . ? O2 U1 N1 131.1(3) 5_666 . ? O2 U1 N1 65.4(3) . . ? O5 U1 N1 146.8(3) . . ? O3 U1 U1 90.2(3) . 5_666 ? O4 U1 U1 92.3(3) . 5_666 ? O1 U1 U1 165.5(2) . 5_666 ? O2 U1 U1 33.7(2) 5_666 5_666 ? O2 U1 U1 33.5(2) . 5_666 ? O5 U1 U1 114.4(2) . 5_666 ? N1 U1 U1 98.2(2) . 5_666 ? O5 S1 C16 104.7(6) . . ? O5 S1 C17 103.4(6) . . ? C16 S1 C17 98.2(7) . . ? C13 O2 U1 128.3(8) . 5_666 ? C13 O2 U1 110.5(8) . . ? U1 O2 U1 112.8(4) 5_666 . ? S1 O5 U1 131.7(5) . . ? C1 O1 U1 131.9(8) . . ? C11 N1 C12 114.9(11) . . ? C11 N1 U1 126.3(8) . . ? C12 N1 U1 118.5(8) . . ? O2 C13 C12 108.9(11) . . ? N1 C11 C10 125.5(12) . . ? C9 C4 C3 118.5(13) . . ? C9 C4 C5 118.9(15) . . ? C3 C4 C5 122.6(14) . . ? O1 C1 C10 121.0(12) . . ? O1 C1 C2 119.5(13) . . ? C10 C1 C2 119.6(13) . . ? C15 C12 C14 111.9(19) . . ? C15 C12 N1 112.2(13) . . ? C14 C12 N1 110.8(12) . . ? C15 C12 C13 111.4(17) . . ? C14 C12 C13 108.3(16) . . ? N1 C12 C13 101.8(10) . . ? C7 C8 C9 122.1(15) . . ? C3 C2 C1 121.3(15) . . ? C5 C6 C7 118.8(16) . . ? C1 C10 C9 119.3(12) . . ? C1 C10 C11 122.1(12) . . ? C9 C10 C11 117.7(12) . . ? C8 C7 C6 121.5(17) . . ? O7 C14 C12 113.9(18) . . ? C6 C5 C4 121.9(16) . . ? C4 C9 C8 116.6(13) . . ? C4 C9 C10 119.6(13) . . ? C8 C9 C10 123.8(13) . . ? C2 C3 C4 121.5(14) . . ? O6 C15 C12 118.4(22) . . ? _refine_diff_density_max 2.436 _refine_diff_density_min -1.356 _refine_diff_density_rms 0.286