# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Bal-Demirci, Tulay' _publ_contact_author_email tulaybal@istanbul.edu.tr _publ_section_title ; Synthesis, X-ray Crystal Structures, Thermal and Electrochemical Properties of Thiosemicarbazidatodioxouranium(VI) complexes ; loop_ _publ_author_name T.Bal-Demirci M.Azahin N.-k.A--zdemir A.-f.Koca M.DANAer ; O.BA1/4yA1/4kgA1/4ngAr ; B.AoelkA1/4seven data_muh73 _database_code_depnum_ccdc_archive 'CCDC 755064' #TrackingRef 'muh73.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H35 Cl2 N3 O5 S U' _chemical_formula_sum 'C27 H35 Cl2 N3 O5 S U' _chemical_formula_weight 822.57 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' Cl Cl 0.1484 0.1585 '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 triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7379(5) _cell_length_b 12.8908(6) _cell_length_c 13.8735(8) _cell_angle_alpha 68.857(4) _cell_angle_beta 86.466(4) _cell_angle_gamma 78.133(5) _cell_volume 1589.43(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296 _cell_measurement_reflns_used 109807 _cell_measurement_theta_min 1.57 _cell_measurement_theta_max 28.14 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.68 _exptl_crystal_size_mid 0.44 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.719 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 5.378 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.0448 _exptl_absorpt_correction_T_max 0.4547 _exptl_absorpt_process_details 'X-RED32 (Stoe & Cie, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_radiation_monochromator 'plane graphite' _diffrn_radiation_collimation '0.8 mm diameter, multiple pinhole' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'w scans' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 35703 _diffrn_reflns_av_R_equivalents 0.0638 _diffrn_reflns_av_sigmaI/netI 0.0329 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.00 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measured_fraction_theta_full 1.000 _reflns_number_total 6236 _reflns_number_gt 5593 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement X-AREA _computing_data_reduction X-RED32 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)' _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^)+(0.0392P)^2^+1.0304P] 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 6236 _refine_ls_number_parameters 352 _refine_ls_number_restraints 91 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0377 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0817 _refine_ls_goodness_of_fit_ref 1.127 _refine_ls_restrained_S_all 1.178 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.688 _refine_diff_density_min -1.107 _refine_diff_density_rms 0.083 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 U1 U 0.51917(2) 0.712102(16) 0.500952(19) 0.05761(9) Uani 1 1 d . . . Cl1 Cl 0.1493(3) 0.9088(2) 0.2313(2) 0.1234(8) Uani 1 1 d . . . Cl2 Cl -0.0963(2) 1.23545(15) 0.3759(2) 0.1138(8) Uani 1 1 d . . . S1 S 0.6838(2) 0.7577(2) 0.82549(19) 0.1045(6) Uani 1 1 d U . . O1 O 0.3590(5) 0.8529(3) 0.3956(4) 0.0792(12) Uani 1 1 d . . . O2 O 0.6544(4) 0.5349(3) 0.5668(4) 0.0697(11) Uani 1 1 d . . . O3 O 0.6568(4) 0.7741(3) 0.4302(4) 0.0749(11) Uani 1 1 d . . . O4 O 0.3856(4) 0.6489(3) 0.5746(4) 0.0712(11) Uani 1 1 d . . . O5 O 0.4936(5) 0.6332(4) 0.3690(4) 0.0783(11) Uani 1 1 d U . . H5O H 0.4422 0.5868 0.3887 0.094 Uiso 1 1 calc R . . N1 N 0.4440(5) 0.8669(4) 0.5779(4) 0.0651(12) Uani 1 1 d . . . N2 N 0.5070(6) 0.8573(5) 0.6717(5) 0.0768(14) Uani 1 1 d . . . N3 N 0.6587(5) 0.6947(4) 0.6597(4) 0.0657(12) Uani 1 1 d . . . C1 C 0.2562(6) 0.9364(5) 0.3939(6) 0.0698(16) Uani 1 1 d . . . C2 C 0.1486(8) 0.9764(5) 0.3184(6) 0.0832(19) Uani 1 1 d . . . C3 C 0.0402(7) 1.0679(6) 0.3143(7) 0.090(2) Uani 1 1 d . . . H3 H -0.0314 1.0922 0.2651 0.108 Uiso 1 1 calc R . . C4 C 0.0405(7) 1.1217(5) 0.3836(7) 0.084(2) Uani 1 1 d . . . C5 C 0.1395(7) 1.0859(5) 0.4572(6) 0.080(2) Uani 1 1 d . . . H5 H 0.1368 1.1232 0.5037 0.096 Uiso 1 1 calc R . . C6 C 0.2479(6) 0.9921(4) 0.4651(6) 0.0707(17) Uani 1 1 d . . . C7 C 0.3437(7) 0.9551(5) 0.5508(6) 0.0702(16) Uani 1 1 d . . . H7 H 0.3323 0.9998 0.5916 0.084 Uiso 1 1 calc R . . C8 C 0.6081(7) 0.7730(6) 0.7077(6) 0.0731(15) Uani 1 1 d U . . C9 C 0.7830(6) 0.6302(5) 0.6882(5) 0.0721(16) Uani 1 1 d . . . H9 H 0.8318 0.6447 0.7360 0.087 Uiso 1 1 calc R . . C10 C 0.8525(6) 0.5402(5) 0.6547(5) 0.0686(15) Uani 1 1 d . . . C11 C 0.9932(7) 0.4905(6) 0.6887(6) 0.085(2) Uani 1 1 d . . . H11 H 1.0373 0.5190 0.7285 0.102 Uiso 1 1 calc R . . C12 C 1.0647(7) 0.4005(7) 0.6633(7) 0.094(2) Uani 1 1 d . . . H12 H 1.1577 0.3695 0.6845 0.113 Uiso 1 1 calc R . . C13 C 0.9993(7) 0.3564(6) 0.6071(7) 0.085(2) Uani 1 1 d . . . H13 H 1.0483 0.2949 0.5910 0.102 Uiso 1 1 calc R . . C14 C 0.8631(6) 0.4010(5) 0.5740(6) 0.0750(17) Uani 1 1 d . . . H14 H 0.8206 0.3693 0.5361 0.090 Uiso 1 1 calc R . . C15 C 0.7871(6) 0.4940(5) 0.5967(5) 0.0669(15) Uani 1 1 d . . . C16 C 0.5875(11) 0.8872(10) 0.8471(10) 0.138(3) Uani 1 1 d U . . H16A H 0.6416 0.9036 0.8944 0.166 Uiso 1 1 calc R . . H16B H 0.5787 0.9508 0.7820 0.166 Uiso 1 1 calc R . . C17 C 0.4490(13) 0.8763(11) 0.8888(11) 0.154(3) Uani 1 1 d U . . H17A H 0.4575 0.8218 0.9590 0.185 Uiso 1 1 calc R . . H17B H 0.3994 0.8483 0.8477 0.185 Uiso 1 1 calc R . . C18 C 0.3659(16) 0.9900(13) 0.8885(13) 0.192(4) Uani 1 1 d U . . H18A H 0.3577 1.0439 0.8190 0.230 Uiso 1 1 calc R . . H18B H 0.4135 1.0165 0.9309 0.230 Uiso 1 1 calc R . . H18C H 0.2740 0.9813 0.9153 0.230 Uiso 1 1 calc R . . C19 C 0.4715(11) 0.6951(8) 0.2604(7) 0.1132(17) Uani 1 1 d U . . H19A H 0.5416 0.7421 0.2360 0.136 Uiso 1 1 calc R . . H19B H 0.3802 0.7452 0.2497 0.136 Uiso 1 1 calc R . . C20 C 0.4787(12) 0.6218(10) 0.1968(8) 0.1288(18) Uani 1 1 d U . . H20A H 0.4246 0.5635 0.2307 0.155 Uiso 1 1 calc R . . H20B H 0.4342 0.6680 0.1303 0.155 Uiso 1 1 calc R . . C21 C 0.6161(13) 0.5682(11) 0.1796(10) 0.145(2) Uani 1 1 d U . . H21A H 0.6591 0.5233 0.2469 0.174 Uiso 1 1 calc R . . H21B H 0.6691 0.6277 0.1474 0.174 Uiso 1 1 calc R . . C22 C 0.6377(15) 0.4943(12) 0.1175(10) 0.156(2) Uani 1 1 d U . . H22A H 0.5889 0.4329 0.1533 0.188 Uiso 1 1 calc R . . H22B H 0.5864 0.5383 0.0531 0.188 Uiso 1 1 calc R . . C23 C 0.7657(15) 0.4441(13) 0.0902(11) 0.171(2) Uani 1 1 d U . . H23A H 0.8136 0.5064 0.0559 0.205 Uiso 1 1 calc R . . H23B H 0.8155 0.4008 0.1553 0.205 Uiso 1 1 calc R . . C24 C 0.7959(16) 0.3762(13) 0.0333(12) 0.183(3) Uani 1 1 d U . . H24A H 0.7579 0.4237 -0.0349 0.219 Uiso 1 1 calc R . . H24B H 0.7366 0.3205 0.0612 0.219 Uiso 1 1 calc R . . C25 C 0.9205(18) 0.3159(14) 0.0154(13) 0.195(3) Uani 1 1 d U . . H25A H 0.9605 0.2678 0.0829 0.234 Uiso 1 1 calc R . . H25B H 0.9805 0.3706 -0.0147 0.234 Uiso 1 1 calc R . . C26 C 0.9389(16) 0.2465(14) -0.0444(13) 0.201(3) Uani 1 1 d DU . . H26A H 0.8726 0.1961 -0.0201 0.242 Uiso 1 1 calc R . . H26B H 0.9113 0.2952 -0.1148 0.242 Uiso 1 1 calc R . . C27 C 1.0651(16) 0.1820(14) -0.0483(14) 0.216(5) Uani 1 1 d DU . . H27A H 1.1326 0.2298 -0.0755 0.259 Uiso 1 1 calc R . . H27B H 1.0590 0.1401 -0.0922 0.259 Uiso 1 1 calc R . . H27C H 1.0937 0.1302 0.0200 0.259 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U1 0.05488(12) 0.05010(11) 0.07286(16) -0.02789(9) -0.00176(9) -0.00945(8) Cl1 0.1399(19) 0.0990(14) 0.131(2) -0.0494(14) -0.0514(16) 0.0082(13) Cl2 0.0883(12) 0.0673(9) 0.155(2) -0.0193(11) 0.0164(13) 0.0108(9) S1 0.1105(15) 0.1303(17) 0.0925(15) -0.0622(14) -0.0102(12) -0.0221(13) O1 0.086(3) 0.060(2) 0.088(3) -0.032(2) -0.016(2) 0.008(2) O2 0.058(2) 0.056(2) 0.101(3) -0.036(2) -0.012(2) -0.0040(17) O3 0.073(2) 0.072(2) 0.091(3) -0.039(2) 0.007(2) -0.021(2) O4 0.064(2) 0.066(2) 0.088(3) -0.032(2) -0.001(2) -0.0124(18) O5 0.097(3) 0.069(2) 0.078(3) -0.033(2) -0.007(2) -0.022(2) N1 0.067(3) 0.053(2) 0.083(4) -0.033(2) 0.002(2) -0.014(2) N2 0.089(4) 0.071(3) 0.086(4) -0.045(3) 0.003(3) -0.021(3) N3 0.064(3) 0.065(3) 0.076(3) -0.032(3) 0.002(2) -0.019(2) C1 0.068(3) 0.051(3) 0.087(5) -0.023(3) 0.000(3) -0.009(3) C2 0.088(4) 0.059(3) 0.097(6) -0.024(3) 0.000(4) -0.009(3) C3 0.071(4) 0.065(4) 0.110(6) -0.006(4) -0.005(4) -0.006(3) C4 0.074(4) 0.049(3) 0.115(6) -0.018(4) 0.014(4) -0.005(3) C5 0.078(4) 0.056(3) 0.100(6) -0.026(3) 0.019(4) -0.011(3) C6 0.070(4) 0.046(3) 0.095(5) -0.024(3) 0.009(3) -0.013(3) C7 0.082(4) 0.055(3) 0.083(5) -0.033(3) 0.014(3) -0.022(3) C8 0.074(4) 0.079(4) 0.080(4) -0.037(3) 0.002(3) -0.027(3) C9 0.068(4) 0.080(4) 0.076(4) -0.031(3) -0.007(3) -0.025(3) C10 0.060(3) 0.070(3) 0.078(4) -0.028(3) -0.005(3) -0.013(3) C11 0.065(4) 0.100(5) 0.094(5) -0.038(4) -0.015(3) -0.013(3) C12 0.058(4) 0.100(5) 0.114(7) -0.031(5) -0.015(4) 0.001(4) C13 0.060(3) 0.074(4) 0.117(6) -0.034(4) -0.002(4) -0.002(3) C14 0.063(3) 0.066(3) 0.097(5) -0.033(3) -0.003(3) -0.005(3) C15 0.053(3) 0.061(3) 0.082(4) -0.020(3) -0.002(3) -0.011(2) C16 0.148(6) 0.176(6) 0.142(7) -0.115(6) 0.023(5) -0.042(5) C17 0.157(6) 0.187(6) 0.150(7) -0.104(6) 0.035(5) -0.031(5) C18 0.189(8) 0.199(8) 0.188(9) -0.096(8) 0.047(7) -0.003(7) C19 0.136(4) 0.108(3) 0.088(3) -0.029(3) -0.012(3) -0.015(3) C20 0.155(4) 0.139(4) 0.091(3) -0.044(3) -0.016(4) -0.014(3) C21 0.165(4) 0.153(4) 0.110(4) -0.051(3) -0.007(4) -0.007(4) C22 0.177(5) 0.170(5) 0.121(4) -0.063(3) -0.006(4) -0.007(4) C23 0.191(5) 0.179(5) 0.138(5) -0.070(4) -0.004(4) 0.002(4) C24 0.203(6) 0.191(6) 0.149(5) -0.078(4) 0.000(5) 0.006(5) C25 0.212(6) 0.197(6) 0.163(6) -0.078(4) 0.001(5) 0.014(5) C26 0.217(7) 0.202(7) 0.169(6) -0.081(5) 0.006(6) 0.021(5) C27 0.226(9) 0.202(9) 0.188(9) -0.075(7) 0.000(8) 0.034(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 1.752(4) . ? U1 O3 1.764(4) . ? U1 O1 2.251(4) . ? U1 O2 2.278(4) . ? U1 O5 2.440(4) . ? U1 N1 2.548(5) . ? U1 N3 2.575(5) . ? Cl1 C2 1.725(8) . ? Cl2 C4 1.743(7) . ? S1 C8 1.763(7) . ? S1 C16 1.854(10) . ? O1 C1 1.305(7) . ? O2 C15 1.322(7) . ? O5 C19 1.433(10) . ? O5 H5O 0.8200 . ? N1 C7 1.292(8) . ? N1 N2 1.427(8) . ? N2 C8 1.277(9) . ? N3 C9 1.312(8) . ? N3 C8 1.395(8) . ? C1 C6 1.405(10) . ? C1 C2 1.408(10) . ? C2 C3 1.399(10) . ? C3 C4 1.374(12) . ? C3 H3 0.9300 . ? C4 C5 1.335(11) . ? C5 C6 1.408(8) . ? C5 H5 0.9300 . ? C6 C7 1.434(10) . ? C7 H7 0.9300 . ? C9 C10 1.431(9) . ? C9 H9 0.9300 . ? C10 C15 1.405(9) . ? C10 C11 1.418(9) . ? C11 C12 1.374(11) . ? C11 H11 0.9300 . ? C12 C13 1.368(11) . ? C12 H12 0.9300 . ? C13 C14 1.367(9) . ? C13 H13 0.9300 . ? C14 C15 1.401(9) . ? C14 H14 0.9300 . ? C16 C17 1.449(13) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.520(17) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.498(14) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.423(14) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.478(17) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.379(16) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.357(18) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.361(17) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.40(2) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.344(14) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O4 U1 O3 178.3(2) . . ? O4 U1 O1 90.73(18) . . ? O3 U1 O1 90.7(2) . . ? O4 U1 O2 84.68(17) . . ? O3 U1 O2 94.29(18) . . ? O1 U1 O2 156.84(16) . . ? O4 U1 O5 91.47(18) . . ? O3 U1 O5 89.65(18) . . ? O1 U1 O5 79.65(16) . . ? O2 U1 O5 77.80(16) . . ? O4 U1 N1 86.21(17) . . ? O3 U1 N1 93.46(17) . . ? O1 U1 N1 70.65(17) . . ? O2 U1 N1 131.38(17) . . ? O5 U1 N1 150.16(17) . . ? O4 U1 N3 94.13(18) . . ? O3 U1 N3 84.23(19) . . ? O1 U1 N3 132.81(15) . . ? O2 U1 N3 70.26(15) . . ? O5 U1 N3 146.86(16) . . ? N1 U1 N3 62.92(16) . . ? C8 S1 C16 101.3(5) . . ? C1 O1 U1 142.9(5) . . ? C15 O2 U1 134.9(3) . . ? C19 O5 U1 126.5(5) . . ? C19 O5 H5O 109.5 . . ? U1 O5 H5O 110.9 . . ? C7 N1 N2 109.1(5) . . ? C7 N1 U1 130.3(5) . . ? N2 N1 U1 120.3(3) . . ? C8 N2 N1 115.7(5) . . ? C9 N3 C8 117.8(6) . . ? C9 N3 U1 124.6(4) . . ? C8 N3 U1 116.7(4) . . ? O1 C1 C6 122.3(6) . . ? O1 C1 C2 121.0(7) . . ? C6 C1 C2 116.7(6) . . ? C3 C2 C1 121.3(8) . . ? C3 C2 Cl1 119.6(7) . . ? C1 C2 Cl1 119.1(5) . . ? C4 C3 C2 119.4(8) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C5 C4 C3 121.3(6) . . ? C5 C4 Cl2 120.7(7) . . ? C3 C4 Cl2 118.0(7) . . ? C4 C5 C6 120.6(8) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 120.6(7) . . ? C1 C6 C7 122.8(5) . . ? C5 C6 C7 116.6(7) . . ? N1 C7 C6 127.5(6) . . ? N1 C7 H7 116.3 . . ? C6 C7 H7 116.3 . . ? N2 C8 N3 123.8(6) . . ? N2 C8 S1 116.3(5) . . ? N3 C8 S1 120.0(5) . . ? N3 C9 C10 127.8(6) . . ? N3 C9 H9 116.1 . . ? C10 C9 H9 116.1 . . ? C15 C10 C11 118.7(6) . . ? C15 C10 C9 124.0(5) . . ? C11 C10 C9 117.1(6) . . ? C12 C11 C10 120.4(7) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C13 C12 C11 120.0(6) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C12 121.2(7) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C13 C14 C15 120.6(7) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? O2 C15 C14 120.3(6) . . ? O2 C15 C10 120.7(5) . . ? C14 C15 C10 119.0(6) . . ? C17 C16 S1 112.8(8) . . ? C17 C16 H16A 109.0 . . ? S1 C16 H16A 109.0 . . ? C17 C16 H16B 109.0 . . ? S1 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 C18 110.7(11) . . ? C16 C17 H17A 109.5 . . ? C18 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? C18 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C19 C20 114.1(8) . . ? O5 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? O5 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C21 C20 C19 115.4(10) . . ? C21 C20 H20A 108.4 . . ? C19 C20 H20A 108.4 . . ? C21 C20 H20B 108.4 . . ? C19 C20 H20B 108.4 . . ? H20A C20 H20B 107.5 . . ? C20 C21 C22 120.7(12) . . ? C20 C21 H21A 107.1 . . ? C22 C21 H21A 107.1 . . ? C20 C21 H21B 107.1 . . ? C22 C21 H21B 107.1 . . ? H21A C21 H21B 106.8 . . ? C23 C22 C21 125.8(13) . . ? C23 C22 H22A 105.9 . . ? C21 C22 H22A 105.9 . . ? C23 C22 H22B 105.9 . . ? C21 C22 H22B 105.9 . . ? H22A C22 H22B 106.2 . . ? C24 C23 C22 130.1(16) . . ? C24 C23 H23A 104.8 . . ? C22 C23 H23A 104.8 . . ? C24 C23 H23B 104.8 . . ? C22 C23 H23B 104.8 . . ? H23A C23 H23B 105.8 . . ? C23 C24 C25 130.8(17) . . ? C23 C24 H24A 104.6 . . ? C25 C24 H24A 104.6 . . ? C23 C24 H24B 104.6 . . ? C25 C24 H24B 104.6 . . ? H24A C24 H24B 105.7 . . ? C24 C25 C26 125.7(17) . . ? C24 C25 H25A 105.9 . . ? C26 C25 H25A 105.9 . . ? C24 C25 H25B 105.9 . . ? C26 C25 H25B 105.9 . . ? H25A C25 H25B 106.2 . . ? C27 C26 C25 120.4(17) . . ? C27 C26 H26A 107.2 . . ? C25 C26 H26A 107.2 . . ? C27 C26 H26B 107.2 . . ? C25 C26 H26B 107.2 . . ? H26A C26 H26B 106.9 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O4 U1 O1 C1 62.1(7) . . . . ? O3 U1 O1 C1 -117.0(7) . . . . ? O2 U1 O1 C1 140.2(6) . . . . ? O5 U1 O1 C1 153.5(7) . . . . ? N1 U1 O1 C1 -23.6(6) . . . . ? N3 U1 O1 C1 -34.2(7) . . . . ? O4 U1 O2 C15 -144.1(6) . . . . ? O3 U1 O2 C15 34.6(6) . . . . ? O1 U1 O2 C15 136.6(6) . . . . ? O5 U1 O2 C15 123.3(6) . . . . ? N1 U1 O2 C15 -63.9(6) . . . . ? N3 U1 O2 C15 -47.7(6) . . . . ? O4 U1 O5 C19 126.6(6) . . . . ? O3 U1 O5 C19 -54.7(6) . . . . ? O1 U1 O5 C19 36.1(6) . . . . ? O2 U1 O5 C19 -149.2(6) . . . . ? N1 U1 O5 C19 41.6(7) . . . . ? N3 U1 O5 C19 -133.6(6) . . . . ? O4 U1 N1 C7 -82.6(5) . . . . ? O3 U1 N1 C7 99.1(5) . . . . ? O1 U1 N1 C7 9.5(5) . . . . ? O2 U1 N1 C7 -162.1(5) . . . . ? O5 U1 N1 C7 3.7(7) . . . . ? N3 U1 N1 C7 -179.2(6) . . . . ? O4 U1 N1 N2 90.4(4) . . . . ? O3 U1 N1 N2 -87.9(4) . . . . ? O1 U1 N1 N2 -177.5(4) . . . . ? O2 U1 N1 N2 10.9(5) . . . . ? O5 U1 N1 N2 176.8(3) . . . . ? N3 U1 N1 N2 -6.2(4) . . . . ? C7 N1 N2 C8 179.8(5) . . . . ? U1 N1 N2 C8 5.4(7) . . . . ? O4 U1 N3 C9 113.7(5) . . . . ? O3 U1 N3 C9 -65.8(5) . . . . ? O1 U1 N3 C9 -151.5(4) . . . . ? O2 U1 N3 C9 30.8(4) . . . . ? O5 U1 N3 C9 14.6(6) . . . . ? N1 U1 N3 C9 -162.7(5) . . . . ? O4 U1 N3 C8 -77.2(4) . . . . ? O3 U1 N3 C8 103.3(4) . . . . ? O1 U1 N3 C8 17.6(5) . . . . ? O2 U1 N3 C8 -160.1(4) . . . . ? O5 U1 N3 C8 -176.3(4) . . . . ? N1 U1 N3 C8 6.4(4) . . . . ? U1 O1 C1 C6 26.6(10) . . . . ? U1 O1 C1 C2 -154.4(5) . . . . ? O1 C1 C2 C3 -178.2(6) . . . . ? C6 C1 C2 C3 0.9(10) . . . . ? O1 C1 C2 Cl1 3.2(9) . . . . ? C6 C1 C2 Cl1 -177.8(5) . . . . ? C1 C2 C3 C4 1.6(11) . . . . ? Cl1 C2 C3 C4 -179.8(5) . . . . ? C2 C3 C4 C5 -2.4(11) . . . . ? C2 C3 C4 Cl2 180.0(5) . . . . ? C3 C4 C5 C6 0.7(10) . . . . ? Cl2 C4 C5 C6 178.3(5) . . . . ? O1 C1 C6 C5 176.5(6) . . . . ? C2 C1 C6 C5 -2.5(9) . . . . ? O1 C1 C6 C7 -5.9(9) . . . . ? C2 C1 C6 C7 175.0(6) . . . . ? C4 C5 C6 C1 1.9(9) . . . . ? C4 C5 C6 C7 -175.9(6) . . . . ? N2 N1 C7 C6 -175.9(6) . . . . ? U1 N1 C7 C6 -2.2(9) . . . . ? C1 C6 C7 N1 -3.1(10) . . . . ? C5 C6 C7 N1 174.5(6) . . . . ? N1 N2 C8 N3 1.2(9) . . . . ? N1 N2 C8 S1 -178.2(4) . . . . ? C9 N3 C8 N2 162.9(6) . . . . ? U1 N3 C8 N2 -7.0(8) . . . . ? C9 N3 C8 S1 -17.7(8) . . . . ? U1 N3 C8 S1 172.4(3) . . . . ? C16 S1 C8 N2 -4.5(6) . . . . ? C16 S1 C8 N3 176.0(5) . . . . ? C8 N3 C9 C10 176.1(6) . . . . ? U1 N3 C9 C10 -14.9(9) . . . . ? N3 C9 C10 C15 -10.9(11) . . . . ? N3 C9 C10 C11 173.6(6) . . . . ? C15 C10 C11 C12 1.4(11) . . . . ? C9 C10 C11 C12 177.2(7) . . . . ? C10 C11 C12 C13 -1.6(13) . . . . ? C11 C12 C13 C14 0.8(13) . . . . ? C12 C13 C14 C15 0.3(12) . . . . ? U1 O2 C15 C14 -140.1(5) . . . . ? U1 O2 C15 C10 42.2(9) . . . . ? C13 C14 C15 O2 -178.3(6) . . . . ? C13 C14 C15 C10 -0.5(10) . . . . ? C11 C10 C15 O2 177.4(6) . . . . ? C9 C10 C15 O2 1.9(10) . . . . ? C11 C10 C15 C14 -0.3(10) . . . . ? C9 C10 C15 C14 -175.8(6) . . . . ? C8 S1 C16 C17 79.7(10) . . . . ? S1 C16 C17 C18 -170.7(11) . . . . ? U1 O5 C19 C20 172.4(6) . . . . ? O5 C19 C20 C21 -76.2(13) . . . . ? C19 C20 C21 C22 -179.6(11) . . . . ? C20 C21 C22 C23 175.5(14) . . . . ? C21 C22 C23 C24 -179.5(16) . . . . ? C22 C23 C24 C25 -171.6(17) . . . . ? C23 C24 C25 C26 179.1(18) . . . . ? C24 C25 C26 C27 -173.3(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C19 H19B Cl1 0.97 2.70 3.660(10) 169.5 . C17 H17B N2 0.97 2.57 3.117(14) 115.8 . C9 H9 S1 0.93 2.44 2.940(7) 113.5 . O5 H5O O2 0.82 1.89 2.703(6) 172.2 2_666 data_muh74 _database_code_depnum_ccdc_archive 'CCDC 755065' #TrackingRef 'muh74.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H35 Cl2 N3 O5 S U' _chemical_formula_sum 'C27 H35 Cl2 N3 O5 S U' _chemical_formula_weight 822.57 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' Cl Cl 0.1484 0.1585 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 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 17.2723(6) _cell_length_b 8.8205(2) _cell_length_c 21.5224(7) _cell_angle_alpha 90.00 _cell_angle_beta 109.180(3) _cell_angle_gamma 90.00 _cell_volume 3096.93(16) _cell_formula_units_Z 4 _cell_measurement_temperature 296 _cell_measurement_reflns_used 52393 _cell_measurement_theta_min 1.25 _cell_measurement_theta_max 27.31 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.764 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 5.521 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.1036 _exptl_absorpt_correction_T_max 0.4681 _exptl_absorpt_process_details 'X-RED32 (Stoe & Cie, 2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed X-ray tube, 12 x 0.4 mm long-fine focus' _diffrn_radiation_monochromator 'plane graphite' _diffrn_measurement_device_type 'STOE IPDS 2' _diffrn_measurement_method 'w scans' _diffrn_detector_area_resol_mean 6.67 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 42498 _diffrn_reflns_av_R_equivalents 0.0677 _diffrn_reflns_av_sigmaI/netI 0.0322 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.25 _diffrn_reflns_theta_max 26.75 _diffrn_reflns_theta_full 26.75 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 6581 _reflns_number_gt 5574 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'X-AREA (Stoe & Cie, 2002)' _computing_cell_refinement X-AREA _computing_data_reduction X-RED32 _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX (Farrugia, 1999) and PLATON (Spek, 2003)' _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^)+(0.0359P)^2^+2.8860P] 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 6581 _refine_ls_number_parameters 352 _refine_ls_number_restraints 91 _refine_ls_R_factor_all 0.0412 _refine_ls_R_factor_gt 0.0320 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0771 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 1.088 _refine_diff_density_min -0.926 _refine_diff_density_rms 0.083 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 U1 U 0.358464(10) 0.439945(18) 0.528506(8) 0.05141(7) Uani 1 1 d . . . Cl1 Cl 0.22332(11) 0.83712(18) 0.38042(9) 0.0940(5) Uani 1 1 d . . . Cl2 Cl 0.00455(15) 0.4760(3) 0.20976(10) 0.1239(8) Uani 1 1 d . . . S1 S 0.14642(11) 0.0155(2) 0.51059(12) 0.0994(6) Uani 1 1 d U . . O1 O 0.4902(2) 0.3610(4) 0.57550(14) 0.0598(8) Uani 1 1 d . . . O2 O 0.2478(2) 0.5760(4) 0.46909(18) 0.0647(9) Uani 1 1 d . . . O3 O 0.36612(19) 0.3635(4) 0.45542(15) 0.0582(8) Uani 1 1 d . . . O4 O 0.3507(2) 0.5217(4) 0.60074(17) 0.0670(9) Uani 1 1 d . . . O5 O 0.4273(2) 0.6624(3) 0.51015(15) 0.0574(7) Uani 1 1 d U . . H5O H 0.4548 0.6589 0.4855 0.086 Uiso 1 1 calc R . . N1 N 0.3626(3) 0.1950(4) 0.5924(2) 0.0603(9) Uani 1 1 d . . . N2 N 0.2953(3) 0.0965(5) 0.5791(2) 0.0716(12) Uani 1 1 d . . . N3 N 0.2292(3) 0.2683(5) 0.4942(2) 0.0629(10) Uani 1 1 d . . . C1 C 0.5314(3) 0.3276(5) 0.6383(2) 0.0567(11) Uani 1 1 d . . . C2 C 0.6100(3) 0.3839(6) 0.6682(2) 0.0665(13) Uani 1 1 d . . . H2 H 0.6330 0.4480 0.6447 0.080 Uiso 1 1 calc R . . C3 C 0.6540(4) 0.3463(7) 0.7320(3) 0.0769(15) Uani 1 1 d . . . H3 H 0.7061 0.3868 0.7513 0.092 Uiso 1 1 calc R . . C4 C 0.6222(4) 0.2491(7) 0.7679(3) 0.0797(16) Uani 1 1 d . . . H4 H 0.6525 0.2239 0.8110 0.096 Uiso 1 1 calc R . . C5 C 0.5455(4) 0.1909(6) 0.7392(2) 0.0734(14) Uani 1 1 d . . . H5 H 0.5244 0.1240 0.7629 0.088 Uiso 1 1 calc R . . C6 C 0.4975(3) 0.2298(5) 0.6743(2) 0.0596(11) Uani 1 1 d . . . C7 C 0.4192(3) 0.1592(6) 0.6468(2) 0.0662(13) Uani 1 1 d . . . H7 H 0.4077 0.0791 0.6705 0.079 Uiso 1 1 calc R . . C8 C 0.2329(4) 0.1334(6) 0.5306(3) 0.0700(13) Uani 1 1 d U . . C9 C 0.1721(3) 0.2814(6) 0.4382(3) 0.0716(14) Uani 1 1 d . . . H9 H 0.1367 0.1993 0.4251 0.086 Uiso 1 1 calc R . . C10 C 0.1566(3) 0.4078(6) 0.3936(3) 0.0674(13) Uani 1 1 d . . . C11 C 0.0979(4) 0.3868(7) 0.3309(3) 0.0822(16) Uani 1 1 d . . . H11 H 0.0716 0.2936 0.3200 0.099 Uiso 1 1 calc R . . C12 C 0.0793(4) 0.5005(8) 0.2865(3) 0.0846(17) Uani 1 1 d . . . C13 C 0.1186(4) 0.6390(7) 0.3011(3) 0.0800(16) Uani 1 1 d . . . H13 H 0.1067 0.7152 0.2695 0.096 Uiso 1 1 calc R . . C14 C 0.1751(3) 0.6647(6) 0.3620(3) 0.0687(13) Uani 1 1 d . . . C15 C 0.1960(3) 0.5499(6) 0.4110(3) 0.0621(12) Uani 1 1 d . . . C16 C 0.1888(5) -0.1490(9) 0.5613(6) 0.158(3) Uani 1 1 d DU . . H16A H 0.2259 -0.1996 0.5427 0.190 Uiso 1 1 calc R . . H16B H 0.2212 -0.1132 0.6047 0.190 Uiso 1 1 calc R . . C17 C 0.1326(6) -0.2577(11) 0.5690(7) 0.170(3) Uani 1 1 d DU . . H17A H 0.1634 -0.3313 0.6012 0.204 Uiso 1 1 calc R . . H17B H 0.1104 -0.3110 0.5275 0.204 Uiso 1 1 calc R . . C18 C 0.0650(6) -0.2096(13) 0.5885(6) 0.176(3) Uani 1 1 d U . . H18A H 0.0379 -0.2967 0.5985 0.263 Uiso 1 1 calc R . . H18B H 0.0271 -0.1534 0.5533 0.263 Uiso 1 1 calc R . . H18C H 0.0845 -0.1463 0.6268 0.263 Uiso 1 1 calc R . . C19 C 0.4203(3) 0.8192(6) 0.5289(2) 0.0624(9) Uani 1 1 d U . . H19A H 0.3856 0.8234 0.5564 0.075 Uiso 1 1 calc R . . H19B H 0.3943 0.8787 0.4897 0.075 Uiso 1 1 calc R . . C20 C 0.5025(3) 0.8870(6) 0.5656(2) 0.0594(9) Uani 1 1 d U . . H20A H 0.4954 0.9951 0.5700 0.071 Uiso 1 1 calc R . . H20B H 0.5381 0.8738 0.5393 0.071 Uiso 1 1 calc R . . C21 C 0.5454(3) 0.8224(6) 0.6333(2) 0.0659(10) Uani 1 1 d U . . H21A H 0.5139 0.8472 0.6619 0.079 Uiso 1 1 calc R . . H21B H 0.5473 0.7128 0.6303 0.079 Uiso 1 1 calc R . . C22 C 0.6314(4) 0.8825(7) 0.6633(3) 0.0729(11) Uani 1 1 d U . . H22A H 0.6289 0.9923 0.6644 0.087 Uiso 1 1 calc R . . H22B H 0.6626 0.8553 0.6349 0.087 Uiso 1 1 calc R . . C23 C 0.6770(4) 0.8261(8) 0.7321(3) 0.0875(13) Uani 1 1 d U . . H23A H 0.6765 0.7161 0.7323 0.105 Uiso 1 1 calc R . . H23B H 0.6490 0.8609 0.7619 0.105 Uiso 1 1 calc R . . C24 C 0.7652(4) 0.8812(9) 0.7567(3) 0.0981(15) Uani 1 1 d U . . H24A H 0.7916 0.8496 0.7254 0.118 Uiso 1 1 calc R . . H24B H 0.7646 0.9912 0.7570 0.118 Uiso 1 1 calc R . . C25 C 0.8163(5) 0.8283(10) 0.8233(4) 0.1109(17) Uani 1 1 d U . . H25A H 0.8163 0.7183 0.8240 0.133 Uiso 1 1 calc R . . H25B H 0.7919 0.8633 0.8554 0.133 Uiso 1 1 calc R . . C26 C 0.9037(5) 0.8838(11) 0.8431(4) 0.1183(19) Uani 1 1 d U . . H26A H 0.9287 0.8445 0.8120 0.142 Uiso 1 1 calc R . . H26B H 0.9033 0.9935 0.8398 0.142 Uiso 1 1 calc R . . C27 C 0.9549(6) 0.8404(13) 0.9097(4) 0.148(3) Uani 1 1 d U . . H27A H 0.9553 0.7320 0.9138 0.177 Uiso 1 1 calc R . . H27B H 0.9331 0.8848 0.9412 0.177 Uiso 1 1 calc R . . H27C H 1.0099 0.8761 0.9178 0.177 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 U1 0.05787(11) 0.04635(10) 0.05538(10) -0.00077(7) 0.02588(7) -0.00145(8) Cl1 0.0999(11) 0.0636(8) 0.1046(11) 0.0116(8) 0.0147(9) -0.0084(8) Cl2 0.1278(17) 0.1059(14) 0.1003(12) -0.0045(11) -0.0139(12) -0.0113(12) S1 0.0776(10) 0.0739(10) 0.1514(17) 0.0183(11) 0.0441(11) -0.0148(8) O1 0.0633(19) 0.066(2) 0.0522(16) 0.0098(14) 0.0222(14) 0.0033(16) O2 0.060(2) 0.0531(19) 0.078(2) -0.0019(16) 0.0187(17) 0.0014(15) O3 0.0584(18) 0.0589(19) 0.0599(17) -0.0008(14) 0.0228(15) -0.0020(15) O4 0.081(2) 0.061(2) 0.069(2) -0.0017(16) 0.0369(18) -0.0021(18) O5 0.0656(18) 0.0482(15) 0.0645(16) -0.0019(13) 0.0295(14) -0.0087(14) N1 0.068(2) 0.049(2) 0.073(2) 0.0043(19) 0.036(2) -0.0001(19) N2 0.072(3) 0.057(2) 0.093(3) 0.009(2) 0.038(3) -0.002(2) N3 0.062(2) 0.054(2) 0.079(3) 0.002(2) 0.032(2) -0.0009(19) C1 0.069(3) 0.053(2) 0.052(2) 0.002(2) 0.025(2) 0.010(2) C2 0.073(3) 0.065(3) 0.062(3) 0.011(2) 0.022(2) 0.003(3) C3 0.079(4) 0.081(4) 0.063(3) 0.005(3) 0.013(3) 0.005(3) C4 0.099(4) 0.082(4) 0.054(3) 0.009(3) 0.020(3) 0.006(3) C5 0.105(4) 0.063(3) 0.060(3) 0.011(2) 0.038(3) 0.011(3) C6 0.078(3) 0.052(3) 0.056(2) 0.005(2) 0.032(2) 0.006(2) C7 0.087(4) 0.053(3) 0.071(3) 0.010(2) 0.043(3) 0.006(3) C8 0.076(3) 0.055(3) 0.093(4) 0.000(3) 0.047(3) -0.004(2) C9 0.068(3) 0.060(3) 0.090(4) -0.003(3) 0.031(3) -0.009(3) C10 0.057(3) 0.063(3) 0.080(3) 0.002(3) 0.020(3) -0.002(2) C11 0.075(4) 0.067(3) 0.098(4) -0.005(3) 0.020(3) -0.010(3) C12 0.080(4) 0.079(4) 0.081(4) -0.004(3) 0.008(3) 0.001(3) C13 0.081(4) 0.070(4) 0.083(4) 0.007(3) 0.019(3) 0.007(3) C14 0.061(3) 0.061(3) 0.082(3) 0.000(3) 0.022(3) 0.000(2) C15 0.052(2) 0.061(3) 0.077(3) -0.001(2) 0.025(2) 0.004(2) C16 0.120(5) 0.094(4) 0.293(8) 0.085(5) 0.113(5) 0.026(3) C17 0.129(5) 0.118(4) 0.298(8) 0.092(5) 0.118(5) 0.026(4) C18 0.136(6) 0.145(6) 0.288(9) 0.094(6) 0.127(6) 0.035(5) C19 0.068(2) 0.0515(19) 0.071(2) -0.0001(18) 0.0264(17) 0.0007(18) C20 0.069(2) 0.0469(18) 0.066(2) -0.0005(17) 0.0280(16) -0.0024(17) C21 0.076(2) 0.057(2) 0.068(2) 0.0006(19) 0.0268(17) -0.0019(19) C22 0.080(2) 0.065(2) 0.073(2) -0.004(2) 0.0240(18) -0.004(2) C23 0.091(2) 0.082(3) 0.082(2) 0.001(2) 0.018(2) -0.004(2) C24 0.093(3) 0.102(3) 0.091(3) 0.003(3) 0.019(2) -0.003(3) C25 0.099(3) 0.115(3) 0.104(3) 0.007(3) 0.014(2) -0.002(3) C26 0.099(3) 0.123(4) 0.117(4) 0.004(3) 0.014(3) -0.005(3) C27 0.122(5) 0.151(6) 0.137(5) 0.015(5) -0.003(4) -0.013(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 1.756(3) . ? U1 O4 1.759(3) . ? U1 O2 2.263(3) . ? U1 O1 2.274(3) . ? U1 O5 2.394(3) . ? U1 N1 2.549(4) . ? U1 N3 2.596(4) . ? Cl1 C14 1.716(6) . ? Cl2 C12 1.743(6) . ? S1 C8 1.753(6) . ? S1 C16 1.819(8) . ? O1 C1 1.337(5) . ? O2 C15 1.297(6) . ? O5 C19 1.457(6) . ? O5 H5O 0.8200 . ? N1 C7 1.294(6) . ? N1 N2 1.403(6) . ? N2 C8 1.272(7) . ? N3 C9 1.287(7) . ? N3 C8 1.415(7) . ? C1 C2 1.388(7) . ? C1 C6 1.410(7) . ? C2 C3 1.374(7) . ? C2 H2 0.9300 . ? C3 C4 1.384(8) . ? C3 H3 0.9300 . ? C4 C5 1.364(8) . ? C4 H4 0.9300 . ? C5 C6 1.411(7) . ? C5 H5 0.9300 . ? C6 C7 1.429(8) . ? C7 H7 0.9300 . ? C9 C10 1.438(8) . ? C9 H9 0.9300 . ? C10 C11 1.409(8) . ? C10 C15 1.417(7) . ? C11 C12 1.350(9) . ? C11 H11 0.9300 . ? C12 C13 1.383(9) . ? C13 C14 1.371(8) . ? C13 H13 0.9300 . ? C14 C15 1.420(7) . ? C16 C17 1.413(8) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.429(12) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C20 1.504(7) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.512(7) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.508(8) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.516(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.518(9) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.490(9) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 C26 1.510(11) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C26 C27 1.467(10) . ? C26 H26A 0.9700 . ? C26 H26B 0.9700 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O3 U1 O4 178.36(15) . . ? O3 U1 O2 89.74(14) . . ? O4 U1 O2 89.21(16) . . ? O3 U1 O1 85.54(13) . . ? O4 U1 O1 95.07(15) . . ? O2 U1 O1 161.70(13) . . ? O3 U1 O5 88.80(13) . . ? O4 U1 O5 89.79(14) . . ? O2 U1 O5 81.10(12) . . ? O1 U1 O5 81.13(12) . . ? O3 U1 N1 99.24(14) . . ? O4 U1 N1 82.40(15) . . ? O2 U1 N1 128.52(13) . . ? O1 U1 N1 69.75(12) . . ? O5 U1 N1 148.92(12) . . ? O3 U1 N3 80.32(14) . . ? O4 U1 N3 100.50(16) . . ? O2 U1 N3 70.16(13) . . ? O1 U1 N3 126.09(13) . . ? O5 U1 N3 149.16(12) . . ? N1 U1 N3 61.85(14) . . ? C8 S1 C16 100.6(4) . . ? C1 O1 U1 129.8(3) . . ? C15 O2 U1 129.6(3) . . ? C19 O5 U1 129.9(3) . . ? C19 O5 H5O 109.5 . . ? U1 O5 H5O 120.0 . . ? C7 N1 N2 111.3(4) . . ? C7 N1 U1 125.0(3) . . ? N2 N1 U1 122.7(3) . . ? C8 N2 N1 115.6(4) . . ? C9 N3 C8 118.4(5) . . ? C9 N3 U1 122.5(3) . . ? C8 N3 U1 117.1(3) . . ? O1 C1 C2 120.3(4) . . ? O1 C1 C6 120.7(5) . . ? C2 C1 C6 118.9(4) . . ? C3 C2 C1 120.8(5) . . ? C3 C2 H2 119.6 . . ? C1 C2 H2 119.6 . . ? C2 C3 C4 121.1(6) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C5 C4 C3 119.0(5) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 121.6(5) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C1 C6 C5 118.5(5) . . ? C1 C6 C7 123.1(4) . . ? C5 C6 C7 118.2(5) . . ? N1 C7 C6 126.9(5) . . ? N1 C7 H7 116.6 . . ? C6 C7 H7 116.6 . . ? N2 C8 N3 122.8(5) . . ? N2 C8 S1 118.3(4) . . ? N3 C8 S1 118.9(4) . . ? N3 C9 C10 127.7(5) . . ? N3 C9 H9 116.1 . . ? C10 C9 H9 116.1 . . ? C11 C10 C15 120.1(5) . . ? C11 C10 C9 117.0(5) . . ? C15 C10 C9 122.8(5) . . ? C12 C11 C10 120.6(6) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.7(6) . . ? C11 C12 Cl2 120.6(5) . . ? C13 C12 Cl2 118.7(5) . . ? C14 C13 C12 120.4(6) . . ? C14 C13 H13 119.8 . . ? C12 C13 H13 119.8 . . ? C13 C14 C15 121.3(5) . . ? C13 C14 Cl1 120.4(4) . . ? C15 C14 Cl1 118.3(4) . . ? O2 C15 C10 122.1(5) . . ? O2 C15 C14 121.1(5) . . ? C10 C15 C14 116.9(5) . . ? C17 C16 S1 117.1(7) . . ? C17 C16 H16A 108.0 . . ? S1 C16 H16A 108.0 . . ? C17 C16 H16B 108.0 . . ? S1 C16 H16B 108.0 . . ? H16A C16 H16B 107.3 . . ? C16 C17 C18 119.5(10) . . ? C16 C17 H17A 107.5 . . ? C18 C17 H17A 107.5 . . ? C16 C17 H17B 107.5 . . ? C18 C17 H17B 107.5 . . ? H17A C17 H17B 107.0 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O5 C19 C20 111.9(4) . . ? O5 C19 H19A 109.2 . . ? C20 C19 H19A 109.2 . . ? O5 C19 H19B 109.2 . . ? C20 C19 H19B 109.2 . . ? H19A C19 H19B 107.9 . . ? C19 C20 C21 115.8(4) . . ? C19 C20 H20A 108.3 . . ? C21 C20 H20A 108.3 . . ? C19 C20 H20B 108.3 . . ? C21 C20 H20B 108.3 . . ? H20A C20 H20B 107.4 . . ? C22 C21 C20 112.4(4) . . ? C22 C21 H21A 109.1 . . ? C20 C21 H21A 109.1 . . ? C22 C21 H21B 109.1 . . ? C20 C21 H21B 109.1 . . ? H21A C21 H21B 107.9 . . ? C21 C22 C23 115.2(5) . . ? C21 C22 H22A 108.5 . . ? C23 C22 H22A 108.5 . . ? C21 C22 H22B 108.5 . . ? C23 C22 H22B 108.5 . . ? H22A C22 H22B 107.5 . . ? C22 C23 C24 112.1(6) . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23B 109.2 . . ? C24 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C25 C24 C23 116.4(6) . . ? C25 C24 H24A 108.2 . . ? C23 C24 H24A 108.2 . . ? C25 C24 H24B 108.2 . . ? C23 C24 H24B 108.2 . . ? H24A C24 H24B 107.3 . . ? C24 C25 C26 113.1(7) . . ? C24 C25 H25A 109.0 . . ? C26 C25 H25A 109.0 . . ? C24 C25 H25B 109.0 . . ? C26 C25 H25B 109.0 . . ? H25A C25 H25B 107.8 . . ? C27 C26 C25 114.6(8) . . ? C27 C26 H26A 108.6 . . ? C25 C26 H26A 108.6 . . ? C27 C26 H26B 108.6 . . ? C25 C26 H26B 108.6 . . ? H26A C26 H26B 107.6 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 U1 O1 C1 -155.8(4) . . . . ? O4 U1 O1 C1 25.7(4) . . . . ? O2 U1 O1 C1 128.7(4) . . . . ? O5 U1 O1 C1 114.7(4) . . . . ? N1 U1 O1 C1 -54.2(4) . . . . ? N3 U1 O1 C1 -81.2(4) . . . . ? O3 U1 O2 C15 25.0(4) . . . . ? O4 U1 O2 C15 -156.2(4) . . . . ? O1 U1 O2 C15 99.9(5) . . . . ? O5 U1 O2 C15 113.9(4) . . . . ? N1 U1 O2 C15 -76.6(5) . . . . ? N3 U1 O2 C15 -54.8(4) . . . . ? O3 U1 O5 C19 149.9(4) . . . . ? O4 U1 O5 C19 -29.3(4) . . . . ? O2 U1 O5 C19 60.0(4) . . . . ? O1 U1 O5 C19 -124.4(4) . . . . ? N1 U1 O5 C19 -104.1(4) . . . . ? N3 U1 O5 C19 81.2(4) . . . . ? O3 U1 N1 C7 117.1(4) . . . . ? O4 U1 N1 C7 -62.9(4) . . . . ? O2 U1 N1 C7 -145.8(4) . . . . ? O1 U1 N1 C7 35.4(4) . . . . ? O5 U1 N1 C7 13.9(5) . . . . ? N3 U1 N1 C7 -169.2(4) . . . . ? O3 U1 N1 N2 -75.7(4) . . . . ? O4 U1 N1 N2 104.3(4) . . . . ? O2 U1 N1 N2 21.4(4) . . . . ? O1 U1 N1 N2 -157.4(4) . . . . ? O5 U1 N1 N2 -178.9(3) . . . . ? N3 U1 N1 N2 -1.9(3) . . . . ? C7 N1 N2 C8 172.2(5) . . . . ? U1 N1 N2 C8 3.4(6) . . . . ? O3 U1 N3 C9 -56.9(4) . . . . ? O4 U1 N3 C9 121.6(4) . . . . ? O2 U1 N3 C9 36.3(4) . . . . ? O1 U1 N3 C9 -134.1(4) . . . . ? O5 U1 N3 C9 14.0(5) . . . . ? N1 U1 N3 C9 -163.0(5) . . . . ? O3 U1 N3 C8 106.4(4) . . . . ? O4 U1 N3 C8 -75.1(4) . . . . ? O2 U1 N3 C8 -160.4(4) . . . . ? O1 U1 N3 C8 29.2(4) . . . . ? O5 U1 N3 C8 177.3(3) . . . . ? N1 U1 N3 C8 0.4(3) . . . . ? U1 O1 C1 C2 -133.4(4) . . . . ? U1 O1 C1 C6 49.3(6) . . . . ? O1 C1 C2 C3 -177.8(5) . . . . ? C6 C1 C2 C3 -0.5(8) . . . . ? C1 C2 C3 C4 1.2(9) . . . . ? C2 C3 C4 C5 -0.3(9) . . . . ? C3 C4 C5 C6 -1.3(9) . . . . ? O1 C1 C6 C5 176.3(4) . . . . ? C2 C1 C6 C5 -1.0(7) . . . . ? O1 C1 C6 C7 1.0(7) . . . . ? C2 C1 C6 C7 -176.3(5) . . . . ? C4 C5 C6 C1 2.0(8) . . . . ? C4 C5 C6 C7 177.5(5) . . . . ? N2 N1 C7 C6 177.1(5) . . . . ? U1 N1 C7 C6 -14.4(7) . . . . ? C1 C6 C7 N1 -14.8(8) . . . . ? C5 C6 C7 N1 169.9(5) . . . . ? N1 N2 C8 N3 -3.1(8) . . . . ? N1 N2 C8 S1 179.7(4) . . . . ? C9 N3 C8 N2 165.4(5) . . . . ? U1 N3 C8 N2 1.4(7) . . . . ? C9 N3 C8 S1 -17.4(7) . . . . ? U1 N3 C8 S1 178.6(2) . . . . ? C16 S1 C8 N2 -11.3(6) . . . . ? C16 S1 C8 N3 171.3(5) . . . . ? C8 N3 C9 C10 179.5(5) . . . . ? U1 N3 C9 C10 -17.4(8) . . . . ? N3 C9 C10 C11 170.9(6) . . . . ? N3 C9 C10 C15 -10.7(9) . . . . ? C15 C10 C11 C12 0.9(10) . . . . ? C9 C10 C11 C12 179.4(6) . . . . ? C10 C11 C12 C13 1.2(11) . . . . ? C10 C11 C12 Cl2 -178.1(5) . . . . ? C11 C12 C13 C14 -2.3(10) . . . . ? Cl2 C12 C13 C14 177.1(5) . . . . ? C12 C13 C14 C15 1.2(9) . . . . ? C12 C13 C14 Cl1 -179.5(5) . . . . ? U1 O2 C15 C10 50.5(7) . . . . ? U1 O2 C15 C14 -130.6(4) . . . . ? C11 C10 C15 O2 177.0(5) . . . . ? C9 C10 C15 O2 -1.4(8) . . . . ? C11 C10 C15 C14 -1.9(8) . . . . ? C9 C10 C15 C14 179.7(5) . . . . ? C13 C14 C15 O2 -178.1(5) . . . . ? Cl1 C14 C15 O2 2.6(7) . . . . ? C13 C14 C15 C10 0.8(8) . . . . ? Cl1 C14 C15 C10 -178.5(4) . . . . ? C8 S1 C16 C17 167.1(10) . . . . ? S1 C16 C17 C18 -50.6(16) . . . . ? U1 O5 C19 C20 127.6(4) . . . . ? O5 C19 C20 C21 -68.1(5) . . . . ? C19 C20 C21 C22 173.0(5) . . . . ? C20 C21 C22 C23 178.2(5) . . . . ? C21 C22 C23 C24 175.4(6) . . . . ? C22 C23 C24 C25 -178.3(7) . . . . ? C23 C24 C25 C26 178.0(7) . . . . ? C24 C25 C26 C27 177.0(8) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C9 H9 S1 0.93 2.42 2.929(6) 114.6 . C16 H16B N2 0.97 2.41 2.785(9) 102.2 . O5 H5O O1 0.82 1.87 2.683(4) 174.6 3_666 # End of Crystallographic Information File