# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 # 1. SUBMISSION DETAILS _publ_contact_author_name 'P. Andrew Evans' _publ_contact_author_address ; Indiana University Department of Chemistry 800 E. Kirkwood Ave. Bloomington, IN 47405-7102 USA ; _publ_contact_author_email paevans@indiana.edu _publ_requested_journal 'Chem. Comm.' _publ_requested_coeditor_name ? _publ_contact_letter ; paper 'in submission' for publication in Chem. Comm.' ; # 3. TITLE AND AUTHOR LIST _publ_section_title ; Diastereoselective metal-catalyzed [4+2+2] carbocyclization reactions utilizing a rhodium(I) N-heterocyclic carbene (NHC) complex: the first example of a rhodium(I)-NHC-catalyzed carbocyclization ; loop_ _publ_author_name _publ_author_address 'Evans, P. Andrew' ; Indiana University Department of Chemistry 800 E. Kirkwood Ave. Bloomington, IN 47405-7102 USA ; 'Baum, Erich W.' ; Indiana University Department of Chemistry 800 E. Kirkwood Ave. Bloomington, IN 47405-7102 USA ; 'Fazal, Aleem N.' ; Indiana University Department of Chemistry 800 E. Kirkwood Ave. Bloomington, IN 47405-7102 USA ; 'Pink, Maren' ; Indiana University Department of Chemistry 800 E. Kirkwood Ave. Bloomington, IN 47405-7102 USA ; #=========================================================================== data_03094 _database_code_depnum_ccdc_archive 'CCDC 249419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H36 Cl N2 Rh' _chemical_formula_sum 'C29 H36 Cl N2 Rh' _chemical_formula_weight 550.96 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rh Rh -1.1178 0.9187 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M I4(1)/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-y+3/4, x+1/4, z+1/4' 'y+3/4, -x+3/4, z+3/4' 'x+1/2, y+1/2, z+1/2' '-x+1, -y+1/2, z+1' '-y+5/4, x+3/4, z+3/4' 'y+5/4, -x+5/4, z+5/4' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'y-3/4, -x-1/4, -z-1/4' '-y-3/4, x-3/4, -z-3/4' '-x+1/2, -y+1/2, -z+1/2' 'x, y+1/2, -z' 'y-1/4, -x+1/4, -z+1/4' '-y-1/4, x-1/4, -z-1/4' _cell_length_a 32.464(2) _cell_length_b 32.464 _cell_length_c 9.9286(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 10463.7(10) _cell_formula_units_Z 16 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 7032 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 30.1 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.399 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 4576 _exptl_absorpt_coefficient_mu 0.774 _exptl_absorpt_correction_type multiscans _exptl_absorpt_correction_T_min 0.8605 _exptl_absorpt_correction_T_max 0.9266 _exptl_absorpt_process_details 'SADABS, R. Blessing (1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details '0.30 degree frames measured for 15 seconds each' _diffrn_measurement_method \w-scans _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_standards_number 913 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 256 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 40629 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0312 _diffrn_reflns_limit_h_min -41 _diffrn_reflns_limit_h_max 45 _diffrn_reflns_limit_k_min -45 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 30.08 _reflns_number_total 7677 _reflns_number_gt 6359 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_structure_solution 'SIR-92 (Alatomare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XTEL (local library)' _computing_publication_material 'XCIF (Bruker, 1999), XTEL (local library)' _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^)+(0.0300P)^2^+11.9930P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7677 _refine_ls_number_parameters 340 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0385 _refine_ls_R_factor_gt 0.0276 _refine_ls_wR_factor_ref 0.0690 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Rh1 Rh 0.647229(4) 0.337113(4) 0.678140(12) 0.01392(4) Uani 1 1 d . . . Cl1 Cl 0.612203(13) 0.399113(13) 0.62232(4) 0.02114(9) Uani 1 1 d . . . N1 N 0.72336(4) 0.36010(4) 0.51807(14) 0.0153(3) Uani 1 1 d . . . N2 N 0.68229(4) 0.32819(4) 0.38539(14) 0.0154(3) Uani 1 1 d . . . C1 C 0.68577(5) 0.34140(5) 0.51526(16) 0.0138(3) Uani 1 1 d . . . C2 C 0.74305(5) 0.35825(6) 0.39346(17) 0.0201(3) Uani 1 1 d . . . H2 H 0.7694 0.3690 0.3715 0.025(6) Uiso 1 1 calc R . . C3 C 0.71713(6) 0.33820(6) 0.31069(18) 0.0211(3) Uani 1 1 d . . . H3 H 0.7217 0.3320 0.2184 0.023(6) Uiso 1 1 calc R . . C4 C 0.74172(5) 0.37627(5) 0.63966(17) 0.0167(3) Uani 1 1 d . . . C5 C 0.76980(5) 0.35178(6) 0.70989(18) 0.0196(3) Uani 1 1 d . . . C6 C 0.78328(6) 0.36588(6) 0.83516(19) 0.0255(4) Uani 1 1 d . . . H6 H 0.8018 0.3494 0.8859 0.027(6) Uiso 1 1 calc R . . C7 C 0.77037(6) 0.40345(7) 0.8878(2) 0.0289(4) Uani 1 1 d . . . C8 C 0.74509(6) 0.42820(6) 0.8097(2) 0.0260(4) Uani 1 1 d . . . H8 H 0.7373 0.4545 0.8429 0.036(7) Uiso 1 1 calc R . . C9 C 0.73075(5) 0.41559(5) 0.68393(18) 0.0193(3) Uani 1 1 d . . . C10 C 0.78679(6) 0.31227(6) 0.6532(2) 0.0245(4) Uani 1 1 d . . . H10A H 0.7659 0.2992 0.5962 0.034(7) Uiso 1 1 calc R . . H10B H 0.7941 0.2937 0.7272 0.043(7) Uiso 1 1 calc R . . H10C H 0.8114 0.3183 0.5994 0.043(7) Uiso 1 1 calc R . . C11 C 0.78399(8) 0.41757(9) 1.0260(2) 0.0443(6) Uani 1 1 d . . . H11A H 0.7915 0.3936 1.0806 0.053(9) Uiso 1 1 calc R . . H11B H 0.7614 0.4325 1.0697 0.110(15) Uiso 1 1 calc R . . H11C H 0.8079 0.4358 1.0172 0.070(10) Uiso 1 1 calc R . . C12 C 0.70581(6) 0.44445(6) 0.5984(2) 0.0250(4) Uani 1 1 d . . . H12A H 0.6922 0.4648 0.6561 0.093(13) Uiso 1 1 calc R . . H12B H 0.6850 0.4288 0.5486 0.046(8) Uiso 1 1 calc R . . H12C H 0.7240 0.4586 0.5346 0.083(11) Uiso 1 1 calc R . . C13 C 0.64945(5) 0.30257(5) 0.33440(15) 0.0150(3) Uani 1 1 d . . . C14 C 0.65608(5) 0.26020(5) 0.32603(17) 0.0176(3) Uani 1 1 d . . . C15 C 0.62394(6) 0.23584(6) 0.27759(18) 0.0219(4) Uani 1 1 d . . . H15 H 0.6278 0.2069 0.2716 0.018(5) Uiso 1 1 calc R . . C16 C 0.58660(6) 0.25258(6) 0.23790(17) 0.0209(4) Uani 1 1 d . . . C17 C 0.58201(6) 0.29516(6) 0.24163(17) 0.0202(3) Uani 1 1 d . . . H17 H 0.5568 0.3070 0.2119 0.029(6) Uiso 1 1 calc R . . C18 C 0.61327(5) 0.32101(5) 0.28773(16) 0.0168(3) Uani 1 1 d . . . C19 C 0.69648(6) 0.24039(6) 0.3634(2) 0.0273(4) Uani 1 1 d . . . H19A H 0.6915 0.2124 0.3964 0.063(9) Uiso 1 1 calc R . . H19B H 0.7099 0.2566 0.4340 0.059(9) Uiso 1 1 calc R . . H19C H 0.7144 0.2393 0.2839 0.060(9) Uiso 1 1 calc R . . C20 C 0.55245(7) 0.22496(7) 0.1892(2) 0.0302(4) Uani 1 1 d . . . H20A H 0.5404 0.2365 0.1069 0.041(7) Uiso 1 1 calc R . . H20B H 0.5312 0.2229 0.2588 0.059(9) Uiso 1 1 calc R . . H20C H 0.5635 0.1975 0.1701 0.050(8) Uiso 1 1 calc R . . C21 C 0.60906(6) 0.36694(6) 0.27854(19) 0.0223(4) Uani 1 1 d . . . H21A H 0.5815 0.3739 0.2456 0.042(7) Uiso 1 1 calc R . . H21B H 0.6298 0.3778 0.2162 0.040(7) Uiso 1 1 calc R . . H21C H 0.6132 0.3791 0.3679 0.030(6) Uiso 1 1 calc R . . C22 C 0.68411(6) 0.28974(6) 0.76189(18) 0.0204(3) Uani 1 1 d . . . H22 H 0.7116 0.2866 0.7176 0.032(6) Uiso 1 1 calc R . . C23 C 0.65123(6) 0.27280(5) 0.68776(18) 0.0200(3) Uani 1 1 d . . . H23 H 0.6600 0.2598 0.6011 0.028(6) Uiso 1 1 calc R . . C24 C 0.61256(6) 0.25418(6) 0.7469(2) 0.0263(4) Uani 1 1 d . . . H24A H 0.6190 0.2264 0.7818 0.042(7) Uiso 1 1 calc R . . H24B H 0.5918 0.2511 0.6746 0.027(6) Uiso 1 1 calc R . . C25 C 0.59413(6) 0.28014(7) 0.8608(2) 0.0296(4) Uani 1 1 d . . . H25A H 0.5643 0.2743 0.8679 0.036(7) Uiso 1 1 calc R . . H25B H 0.6072 0.2722 0.9471 0.051(8) Uiso 1 1 calc R . . C26 C 0.60040(6) 0.32570(6) 0.83734(18) 0.0245(4) Uani 1 1 d . . . H26 H 0.5743 0.3417 0.8259 0.041(7) Uiso 1 1 calc R . . C27 C 0.63291(6) 0.34840(7) 0.88842(18) 0.0250(4) Uani 1 1 d . . . H27 H 0.6258 0.3777 0.9090 0.039(7) Uiso 1 1 calc R . . C28 C 0.66843(7) 0.33164(7) 0.97074(19) 0.0302(4) Uani 1 1 d . . . H28A H 0.6590 0.3271 1.0643 0.035(7) Uiso 1 1 calc R . . H28B H 0.6907 0.3525 0.9734 0.028(6) Uiso 1 1 calc R . . C29 C 0.68600(6) 0.29123(7) 0.91548(19) 0.0275(4) Uani 1 1 d . . . H29A H 0.7150 0.2883 0.9449 0.040(7) Uiso 1 1 calc R . . H29B H 0.6702 0.2678 0.9530 0.024(6) 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 Rh1 0.01479(7) 0.01554(7) 0.01143(6) -0.00043(4) 0.00123(4) 0.00104(5) Cl1 0.0207(2) 0.01698(19) 0.0257(2) -0.00287(16) -0.00086(16) 0.00402(15) N1 0.0148(6) 0.0171(7) 0.0142(6) -0.0002(5) -0.0007(5) -0.0009(5) N2 0.0148(6) 0.0184(7) 0.0132(6) -0.0013(5) 0.0005(5) -0.0004(5) C1 0.0145(7) 0.0129(7) 0.0140(7) 0.0004(6) -0.0014(6) 0.0017(6) C2 0.0166(8) 0.0267(9) 0.0171(7) 0.0004(7) 0.0023(6) -0.0014(7) C3 0.0186(8) 0.0289(9) 0.0158(7) 0.0004(7) 0.0034(6) -0.0022(7) C4 0.0156(8) 0.0178(8) 0.0168(7) -0.0008(6) -0.0024(6) -0.0012(6) C5 0.0155(8) 0.0196(8) 0.0235(8) 0.0001(7) -0.0021(6) -0.0002(6) C6 0.0220(9) 0.0311(10) 0.0234(9) 0.0018(8) -0.0083(7) 0.0028(8) C7 0.0249(10) 0.0381(11) 0.0237(9) -0.0078(8) -0.0076(8) -0.0012(8) C8 0.0249(9) 0.0245(9) 0.0287(9) -0.0100(8) -0.0051(8) 0.0001(7) C9 0.0162(8) 0.0188(8) 0.0230(8) -0.0011(7) -0.0018(7) -0.0005(6) C10 0.0202(9) 0.0220(9) 0.0312(10) 0.0001(7) -0.0010(7) 0.0046(7) C11 0.0445(14) 0.0570(16) 0.0315(11) -0.0175(11) -0.0160(10) 0.0063(12) C12 0.0220(9) 0.0188(9) 0.0342(10) 0.0016(8) -0.0062(8) 0.0019(7) C13 0.0152(7) 0.0187(8) 0.0110(6) -0.0021(6) 0.0010(6) -0.0021(6) C14 0.0187(8) 0.0181(8) 0.0161(7) -0.0013(6) 0.0016(6) 0.0013(6) C15 0.0285(9) 0.0168(8) 0.0204(8) -0.0013(7) 0.0015(7) -0.0020(7) C16 0.0244(9) 0.0235(9) 0.0147(7) -0.0018(7) -0.0001(7) -0.0075(7) C17 0.0187(8) 0.0259(9) 0.0158(7) -0.0001(7) -0.0022(6) -0.0011(7) C18 0.0195(8) 0.0177(8) 0.0132(7) -0.0008(6) 0.0015(6) 0.0007(6) C19 0.0254(10) 0.0250(10) 0.0314(10) -0.0006(8) 0.0001(8) 0.0072(8) C20 0.0314(11) 0.0317(11) 0.0274(10) -0.0040(8) -0.0060(8) -0.0113(9) C21 0.0253(9) 0.0189(8) 0.0227(8) -0.0001(7) -0.0034(7) 0.0026(7) C22 0.0217(9) 0.0218(9) 0.0178(8) 0.0058(7) 0.0017(7) 0.0046(7) C23 0.0262(9) 0.0155(8) 0.0182(8) 0.0036(6) 0.0011(7) 0.0027(7) C24 0.0266(10) 0.0226(9) 0.0296(10) 0.0095(8) -0.0020(8) -0.0038(7) C25 0.0236(10) 0.0397(12) 0.0254(9) 0.0107(8) 0.0046(8) -0.0059(8) C26 0.0207(9) 0.0357(11) 0.0172(8) 0.0010(7) 0.0082(7) 0.0025(8) C27 0.0272(10) 0.0334(10) 0.0145(7) -0.0049(7) 0.0057(7) 0.0040(8) C28 0.0321(11) 0.0439(12) 0.0145(8) -0.0010(8) -0.0013(8) -0.0012(9) C29 0.0277(10) 0.0366(11) 0.0182(8) 0.0073(8) -0.0043(7) 0.0000(8) _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 Rh1 C1 2.0494(16) . ? Rh1 C23 2.0941(17) . ? Rh1 C22 2.1190(17) . ? Rh1 C27 2.1701(17) . ? Rh1 C26 2.2241(18) . ? Rh1 Cl1 2.3773(4) . ? N1 C1 1.363(2) . ? N1 C2 1.394(2) . ? N1 C4 1.445(2) . ? N2 C1 1.364(2) . ? N2 C3 1.391(2) . ? N2 C13 1.444(2) . ? C2 C3 1.344(3) . ? C4 C9 1.396(2) . ? C4 C5 1.396(2) . ? C5 C6 1.396(3) . ? C5 C10 1.505(3) . ? C6 C7 1.392(3) . ? C7 C8 1.386(3) . ? C7 C11 1.513(3) . ? C8 C9 1.394(3) . ? C9 C12 1.502(3) . ? C13 C14 1.394(2) . ? C13 C18 1.398(2) . ? C14 C15 1.395(3) . ? C14 C19 1.507(3) . ? C15 C16 1.385(3) . ? C16 C17 1.391(3) . ? C16 C20 1.506(3) . ? C17 C18 1.394(2) . ? C18 C21 1.500(2) . ? C22 C23 1.408(3) . ? C22 C29 1.527(3) . ? C23 C24 1.512(3) . ? C24 C25 1.532(3) . ? C25 C26 1.511(3) . ? C26 C27 1.383(3) . ? C27 C28 1.515(3) . ? C28 C29 1.532(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 C1 Rh1 C23 93.77(7) . . ? C1 Rh1 C22 90.80(6) . . ? C23 Rh1 C22 39.05(7) . . ? C1 Rh1 C27 151.46(7) . . ? C23 Rh1 C27 97.92(7) . . ? C22 Rh1 C27 82.30(7) . . ? C1 Rh1 C26 171.65(7) . . ? C23 Rh1 C26 81.02(7) . . ? C22 Rh1 C26 89.22(7) . . ? C27 Rh1 C26 36.68(7) . . ? C1 Rh1 Cl1 92.90(5) . . ? C23 Rh1 Cl1 152.19(5) . . ? C22 Rh1 Cl1 167.49(5) . . ? C27 Rh1 Cl1 88.79(6) . . ? C26 Rh1 Cl1 88.84(5) . . ? C1 N1 C2 111.91(14) . . ? C1 N1 C4 123.24(14) . . ? C2 N1 C4 124.61(14) . . ? C1 N2 C3 111.32(14) . . ? C1 N2 C13 125.02(14) . . ? C3 N2 C13 123.23(14) . . ? N1 C1 N2 103.50(14) . . ? N1 C1 Rh1 124.10(11) . . ? N2 C1 Rh1 132.40(12) . . ? C3 C2 N1 106.05(15) . . ? C2 C3 N2 107.22(15) . . ? C9 C4 C5 122.00(16) . . ? C9 C4 N1 119.34(15) . . ? C5 C4 N1 118.65(15) . . ? C6 C5 C4 117.58(17) . . ? C6 C5 C10 119.85(17) . . ? C4 C5 C10 122.53(16) . . ? C7 C6 C5 121.85(18) . . ? C8 C7 C6 118.46(17) . . ? C8 C7 C11 120.3(2) . . ? C6 C7 C11 121.2(2) . . ? C7 C8 C9 121.91(18) . . ? C8 C9 C4 117.73(17) . . ? C8 C9 C12 120.22(17) . . ? C4 C9 C12 122.00(16) . . ? C14 C13 C18 122.19(15) . . ? C14 C13 N2 118.36(15) . . ? C18 C13 N2 119.34(15) . . ? C13 C14 C15 117.66(16) . . ? C13 C14 C19 122.73(16) . . ? C15 C14 C19 119.59(16) . . ? C16 C15 C14 122.01(17) . . ? C15 C16 C17 118.42(16) . . ? C15 C16 C20 120.13(18) . . ? C17 C16 C20 121.43(18) . . ? C16 C17 C18 121.94(17) . . ? C17 C18 C13 117.55(16) . . ? C17 C18 C21 120.80(16) . . ? C13 C18 C21 121.52(16) . . ? C23 C22 C29 124.39(17) . . ? C23 C22 Rh1 69.52(10) . . ? C29 C22 Rh1 113.05(13) . . ? C22 C23 C24 125.63(16) . . ? C22 C23 Rh1 71.43(10) . . ? C24 C23 Rh1 111.39(12) . . ? C23 C24 C25 113.02(16) . . ? C26 C25 C24 111.83(15) . . ? C27 C26 C25 124.58(18) . . ? C27 C26 Rh1 69.54(10) . . ? C25 C26 Rh1 111.39(13) . . ? C26 C27 C28 125.96(19) . . ? C26 C27 Rh1 73.79(10) . . ? C28 C27 Rh1 107.18(12) . . ? C27 C28 C29 113.44(16) . . ? C22 C29 C28 111.71(16) . . ? 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 C2 N1 C1 N2 -0.59(18) . . . . ? C4 N1 C1 N2 -175.17(14) . . . . ? C2 N1 C1 Rh1 179.60(12) . . . . ? C4 N1 C1 Rh1 5.0(2) . . . . ? C3 N2 C1 N1 0.58(18) . . . . ? C13 N2 C1 N1 173.17(15) . . . . ? C3 N2 C1 Rh1 -179.62(13) . . . . ? C13 N2 C1 Rh1 -7.0(2) . . . . ? C23 Rh1 C1 N1 -115.10(14) . . . . ? C22 Rh1 C1 N1 -76.13(14) . . . . ? C27 Rh1 C1 N1 -0.9(2) . . . . ? C26 Rh1 C1 N1 -166.2(4) . . . . ? Cl1 Rh1 C1 N1 91.92(13) . . . . ? C23 Rh1 C1 N2 65.14(16) . . . . ? C22 Rh1 C1 N2 104.12(16) . . . . ? C27 Rh1 C1 N2 179.36(15) . . . . ? C26 Rh1 C1 N2 14.0(6) . . . . ? Cl1 Rh1 C1 N2 -87.84(15) . . . . ? C1 N1 C2 C3 0.4(2) . . . . ? C4 N1 C2 C3 174.88(16) . . . . ? N1 C2 C3 N2 0.0(2) . . . . ? C1 N2 C3 C2 -0.4(2) . . . . ? C13 N2 C3 C2 -173.12(16) . . . . ? C1 N1 C4 C9 -83.4(2) . . . . ? C2 N1 C4 C9 102.7(2) . . . . ? C1 N1 C4 C5 96.1(2) . . . . ? C2 N1 C4 C5 -77.8(2) . . . . ? C9 C4 C5 C6 7.2(3) . . . . ? N1 C4 C5 C6 -172.36(16) . . . . ? C9 C4 C5 C10 -170.49(17) . . . . ? N1 C4 C5 C10 10.0(3) . . . . ? C4 C5 C6 C7 -1.8(3) . . . . ? C10 C5 C6 C7 175.96(19) . . . . ? C5 C6 C7 C8 -3.3(3) . . . . ? C5 C6 C7 C11 177.7(2) . . . . ? C6 C7 C8 C9 3.3(3) . . . . ? C11 C7 C8 C9 -177.7(2) . . . . ? C7 C8 C9 C4 1.8(3) . . . . ? C7 C8 C9 C12 -175.79(19) . . . . ? C5 C4 C9 C8 -7.2(3) . . . . ? N1 C4 C9 C8 172.31(16) . . . . ? C5 C4 C9 C12 170.37(17) . . . . ? N1 C4 C9 C12 -10.1(3) . . . . ? C1 N2 C13 C14 -96.5(2) . . . . ? C3 N2 C13 C14 75.3(2) . . . . ? C1 N2 C13 C18 87.4(2) . . . . ? C3 N2 C13 C18 -100.91(19) . . . . ? C18 C13 C14 C15 -4.5(2) . . . . ? N2 C13 C14 C15 179.49(15) . . . . ? C18 C13 C14 C19 173.88(16) . . . . ? N2 C13 C14 C19 -2.2(2) . . . . ? C13 C14 C15 C16 0.4(3) . . . . ? C19 C14 C15 C16 -177.99(17) . . . . ? C14 C15 C16 C17 2.7(3) . . . . ? C14 C15 C16 C20 -178.63(17) . . . . ? C15 C16 C17 C18 -2.0(3) . . . . ? C20 C16 C17 C18 179.38(17) . . . . ? C16 C17 C18 C13 -1.8(3) . . . . ? C16 C17 C18 C21 174.18(16) . . . . ? C14 C13 C18 C17 5.1(2) . . . . ? N2 C13 C18 C17 -178.85(14) . . . . ? C14 C13 C18 C21 -170.83(16) . . . . ? N2 C13 C18 C21 5.2(2) . . . . ? C1 Rh1 C22 C23 -95.00(11) . . . . ? C27 Rh1 C22 C23 112.79(11) . . . . ? C26 Rh1 C22 C23 76.65(11) . . . . ? Cl1 Rh1 C22 C23 157.75(19) . . . . ? C1 Rh1 C22 C29 145.24(14) . . . . ? C23 Rh1 C22 C29 -119.76(18) . . . . ? C27 Rh1 C22 C29 -6.97(14) . . . . ? C26 Rh1 C22 C29 -43.11(14) . . . . ? Cl1 Rh1 C22 C29 38.0(3) . . . . ? C29 C22 C23 C24 1.1(3) . . . . ? Rh1 C22 C23 C24 -103.45(18) . . . . ? C29 C22 C23 Rh1 104.53(18) . . . . ? C1 Rh1 C23 C22 86.62(11) . . . . ? C27 Rh1 C23 C22 -67.28(11) . . . . ? C26 Rh1 C23 C22 -99.96(11) . . . . ? Cl1 Rh1 C23 C22 -169.87(9) . . . . ? C1 Rh1 C23 C24 -151.48(13) . . . . ? C22 Rh1 C23 C24 121.90(17) . . . . ? C27 Rh1 C23 C24 54.62(14) . . . . ? C26 Rh1 C23 C24 21.94(13) . . . . ? Cl1 Rh1 C23 C24 -47.97(19) . . . . ? C22 C23 C24 C25 44.6(3) . . . . ? Rh1 C23 C24 C25 -37.33(19) . . . . ? C23 C24 C25 C26 34.0(2) . . . . ? C24 C25 C26 C27 -94.1(2) . . . . ? C24 C25 C26 Rh1 -14.8(2) . . . . ? C1 Rh1 C26 C27 168.3(4) . . . . ? C23 Rh1 C26 C27 116.47(13) . . . . ? C22 Rh1 C26 C27 78.11(13) . . . . ? Cl1 Rh1 C26 C27 -89.53(12) . . . . ? C1 Rh1 C26 C25 48.0(5) . . . . ? C23 Rh1 C26 C25 -3.83(14) . . . . ? C22 Rh1 C26 C25 -42.19(14) . . . . ? C27 Rh1 C26 C25 -120.3(2) . . . . ? Cl1 Rh1 C26 C25 150.17(13) . . . . ? C25 C26 C27 C28 2.7(3) . . . . ? Rh1 C26 C27 C28 -99.74(18) . . . . ? C25 C26 C27 Rh1 102.45(18) . . . . ? C1 Rh1 C27 C26 -176.47(13) . . . . ? C23 Rh1 C27 C26 -63.22(13) . . . . ? C22 Rh1 C27 C26 -99.12(13) . . . . ? Cl1 Rh1 C27 C26 89.69(12) . . . . ? C1 Rh1 C27 C28 -53.1(2) . . . . ? C23 Rh1 C27 C28 60.16(15) . . . . ? C22 Rh1 C27 C28 24.26(14) . . . . ? C26 Rh1 C27 C28 123.4(2) . . . . ? Cl1 Rh1 C27 C28 -146.93(14) . . . . ? C26 C27 C28 C29 43.7(3) . . . . ? Rh1 C27 C28 C29 -38.5(2) . . . . ? C23 C22 C29 C28 -92.3(2) . . . . ? Rh1 C22 C29 C28 -12.0(2) . . . . ? C27 C28 C29 C22 34.2(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C2 H2 Cl1 0.95 2.65 3.5095(18) 150.1 7_544 C15 H15 Cl1 0.95 2.75 3.6074(19) 150.8 11_666 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.08 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.546 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.074 data_03220 _database_code_depnum_ccdc_archive 'CCDC 249420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H29 Cl2 N3 O8 S' _chemical_formula_weight 626.49 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.1295(9) _cell_length_b 10.5003(9) _cell_length_c 24.1594(18) _cell_angle_alpha 90.00 _cell_angle_beta 94.137(2) _cell_angle_gamma 90.00 _cell_volume 2816.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 118(2) _cell_measurement_reflns_used 990 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 27.47 _exptl_crystal_description 'cleaved fragment' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.360 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 118(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details ' 0.30 degree frames measured for 2.17 seconds each' _diffrn_measurement_method '\w scans' _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 61670 _diffrn_reflns_av_R_equivalents 0.0806 _diffrn_reflns_av_sigmaI/netI 0.0348 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 27.53 _reflns_number_total 6475 _reflns_number_gt 5311 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction 'SAINT (Bruker, 1999), XTEL (local package)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0966P)^2^+0.3091P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6475 _refine_ls_number_parameters 486 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0549 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1423 _refine_ls_wR_factor_gt 0.1369 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.034 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.58041(19) 0.4491(2) 0.38587(9) 0.0268(4) Uani 1 1 d . . . C2 C 0.53480(16) 0.57327(18) 0.40744(8) 0.0207(4) Uani 1 1 d . . . C3 C 0.58652(18) 0.6106(2) 0.46502(8) 0.0250(4) Uani 1 1 d . . . C4 C 0.70069(18) 0.6859(2) 0.46021(8) 0.0266(4) Uani 1 1 d . . . C5 C 0.70413(18) 0.8104(2) 0.45273(8) 0.0281(4) Uani 1 1 d . . . C6 C 0.5977(2) 0.8991(2) 0.44900(9) 0.0290(4) Uani 1 1 d . . . C7 C 0.51174(17) 0.88919(19) 0.39560(9) 0.0234(4) Uani 1 1 d . . . C8 C 0.41758(15) 0.78079(17) 0.39522(7) 0.0176(3) Uani 1 1 d . . . C9 C 0.46402(16) 0.65278(17) 0.37687(7) 0.0183(3) Uani 1 1 d . . . C10 C 0.42348(17) 0.63098(18) 0.31659(8) 0.0198(4) Uani 1 1 d . . . N11 N 0.33016(13) 0.72860(14) 0.30427(6) 0.0167(3) Uani 1 1 d . . . C12 C 0.30942(15) 0.80926(17) 0.35303(7) 0.0169(3) Uani 1 1 d . . . C13 C 0.18731(16) 0.78177(16) 0.37380(8) 0.0178(3) Uani 1 1 d . . . O14 O 0.18278(11) 0.64640(11) 0.38679(5) 0.0176(3) Uani 1 1 d . . . C15 C 0.08148(15) 0.60800(17) 0.40791(7) 0.0165(3) Uani 1 1 d . . . O16 O -0.00084(11) 0.67693(13) 0.41810(6) 0.0220(3) Uani 1 1 d . . . C17 C 0.08127(16) 0.46702(17) 0.41820(7) 0.0169(3) Uani 1 1 d . . . C18 C 0.17827(16) 0.39003(17) 0.40759(7) 0.0171(3) Uani 1 1 d . . . C19 C 0.16969(16) 0.26059(17) 0.41794(7) 0.0187(4) Uani 1 1 d . . . N20 N 0.27356(15) 0.17836(15) 0.40977(7) 0.0227(3) Uani 1 1 d . . . O21 O 0.36791(13) 0.22910(14) 0.39846(7) 0.0318(3) Uani 1 1 d . . . O22 O 0.26057(14) 0.06341(13) 0.41600(7) 0.0310(3) Uani 1 1 d . . . C23 C 0.06944(17) 0.20488(18) 0.43851(7) 0.0203(4) Uani 1 1 d . . . C24 C -0.02423(16) 0.28544(18) 0.44918(7) 0.0193(4) Uani 1 1 d . . . N25 N -0.13065(15) 0.22997(16) 0.47336(7) 0.0235(3) Uani 1 1 d . . . O26 O -0.13099(14) 0.11552(15) 0.48199(7) 0.0346(4) Uani 1 1 d . . . O27 O -0.21267(13) 0.30286(15) 0.48363(6) 0.0285(3) Uani 1 1 d . . . C28 C -0.02119(16) 0.41492(18) 0.43938(7) 0.0183(3) Uani 1 1 d . . . S29 S 0.30993(4) 0.78697(4) 0.242289(18) 0.01830(13) Uani 1 1 d . . . O30 O 0.19910(12) 0.85756(13) 0.24021(6) 0.0251(3) Uani 1 1 d . . . O31 O 0.32453(12) 0.68262(13) 0.20484(5) 0.0236(3) Uani 1 1 d . . . C32 C 0.42692(16) 0.89638(17) 0.23254(7) 0.0190(4) Uani 1 1 d . . . C33 C 0.53280(18) 0.8549(2) 0.21103(8) 0.0220(4) Uani 1 1 d . . . C34 C 0.62272(18) 0.9421(2) 0.20219(8) 0.0248(4) Uani 1 1 d . . . C35 C 0.60891(17) 1.07116(19) 0.21403(8) 0.0233(4) Uani 1 1 d . . . C36 C 0.7049(2) 1.1656(2) 0.20102(11) 0.0325(5) Uani 1 1 d . . . C37 C 0.50309(18) 1.11016(19) 0.23706(9) 0.0258(4) Uani 1 1 d . . . C38 C 0.41228(18) 1.02405(18) 0.24611(8) 0.0228(4) Uani 1 1 d . . . Cl39 Cl 0.56380(6) 1.50551(7) 0.18599(4) 0.0539(2) Uani 1 1 d . . . C40 C 0.7094(3) 1.5008(3) 0.16219(13) 0.0442(6) Uani 1 1 d . . . Cl41 Cl 0.76521(6) 1.65245(6) 0.14701(2) 0.04258(17) Uani 1 1 d . . . H42 H 0.673(3) 0.456(3) 0.3874(12) 0.050(8) Uiso 1 1 d . . . H43 H 0.553(3) 0.376(3) 0.4111(12) 0.045(7) Uiso 1 1 d . . . H44 H 0.551(2) 0.429(2) 0.3501(11) 0.032(6) Uiso 1 1 d . . . H45 H 0.606(2) 0.531(2) 0.4891(10) 0.025(6) Uiso 1 1 d . . . H46 H 0.530(2) 0.667(2) 0.4810(10) 0.023(6) Uiso 1 1 d . . . H47 H 0.775(2) 0.644(2) 0.4635(10) 0.030(6) Uiso 1 1 d . . . H48 H 0.783(3) 0.849(3) 0.4523(12) 0.044(8) Uiso 1 1 d . . . H49 H 0.552(2) 0.887(2) 0.4804(10) 0.026(6) Uiso 1 1 d . . . H50 H 0.627(2) 0.973(3) 0.4534(11) 0.036(7) Uiso 1 1 d . . . H51 H 0.467(2) 0.964(2) 0.3922(9) 0.020(5) Uiso 1 1 d . . . H52 H 0.557(2) 0.874(2) 0.3634(11) 0.031(6) Uiso 1 1 d . . . H53 H 0.3889(18) 0.768(2) 0.4328(9) 0.014(5) Uiso 1 1 d . . . H54 H 0.483(2) 0.646(2) 0.2952(10) 0.024(6) Uiso 1 1 d . . . H55 H 0.3897(19) 0.546(2) 0.3098(9) 0.017(5) Uiso 1 1 d . . . H56 H 0.3070(19) 0.902(2) 0.3426(9) 0.016(5) Uiso 1 1 d . . . H57 H 0.1803(19) 0.830(2) 0.4068(9) 0.014(5) Uiso 1 1 d . . . H58 H 0.1268(19) 0.798(2) 0.3461(9) 0.014(5) Uiso 1 1 d . . . H59 H 0.244(2) 0.417(2) 0.3941(10) 0.027(6) Uiso 1 1 d . . . H60 H 0.066(2) 0.112(2) 0.4466(10) 0.028(6) Uiso 1 1 d . . . H61 H -0.083(2) 0.465(2) 0.4468(9) 0.020(5) Uiso 1 1 d . . . H62 H 0.538(2) 0.785(3) 0.2029(10) 0.027(7) Uiso 1 1 d . . . H63 H 0.698(2) 0.915(2) 0.1866(10) 0.031(6) Uiso 1 1 d . . . H64 H 0.795(3) 1.130(4) 0.2020(14) 0.071(10) Uiso 1 1 d . . . H65 H 0.698(3) 1.190(3) 0.1638(14) 0.046(8) Uiso 1 1 d . . . H66 H 0.701(3) 1.244(4) 0.2271(15) 0.069(10) Uiso 1 1 d . . . H67 H 0.491(2) 1.191(2) 0.2504(10) 0.028(6) Uiso 1 1 d . . . H68 H 0.349(2) 1.043(2) 0.2625(10) 0.028(6) Uiso 1 1 d . . . H69 H 0.767(3) 1.462(3) 0.1911(15) 0.066(10) Uiso 1 1 d . . . H70 H 0.693(3) 1.458(3) 0.1311(16) 0.063(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0267(10) 0.0234(10) 0.0301(11) 0.0006(8) 0.0001(8) 0.0059(8) C2 0.0202(8) 0.0210(9) 0.0210(9) 0.0022(7) 0.0023(7) 0.0004(7) C3 0.0260(9) 0.0290(10) 0.0197(9) 0.0038(7) -0.0002(7) 0.0016(8) C4 0.0233(10) 0.0372(11) 0.0186(9) -0.0006(8) -0.0024(7) 0.0026(8) C5 0.0209(9) 0.0400(12) 0.0230(10) 0.0011(8) -0.0021(7) -0.0056(8) C6 0.0284(10) 0.0251(11) 0.0329(11) -0.0057(8) -0.0015(9) -0.0056(8) C7 0.0213(9) 0.0183(9) 0.0304(10) -0.0006(7) 0.0001(8) -0.0021(7) C8 0.0162(8) 0.0172(8) 0.0194(9) -0.0002(6) 0.0024(6) 0.0011(6) C9 0.0184(8) 0.0171(8) 0.0198(9) -0.0006(6) 0.0043(6) -0.0011(6) C10 0.0201(9) 0.0188(9) 0.0205(9) -0.0011(7) 0.0011(7) 0.0043(7) N11 0.0189(7) 0.0152(7) 0.0163(7) 0.0020(5) 0.0027(5) 0.0012(5) C12 0.0167(8) 0.0162(8) 0.0180(8) -0.0006(6) 0.0025(6) -0.0001(6) C13 0.0173(8) 0.0137(8) 0.0227(9) 0.0014(7) 0.0035(7) 0.0017(6) O14 0.0167(6) 0.0161(6) 0.0205(6) 0.0012(5) 0.0053(5) 0.0011(5) C15 0.0167(8) 0.0191(8) 0.0138(8) -0.0011(6) 0.0018(6) -0.0022(6) O16 0.0187(6) 0.0203(7) 0.0276(7) -0.0007(5) 0.0061(5) 0.0018(5) C17 0.0203(8) 0.0181(8) 0.0125(8) -0.0008(6) 0.0022(6) -0.0019(7) C18 0.0188(8) 0.0184(8) 0.0142(8) -0.0008(6) 0.0018(6) -0.0014(7) C19 0.0224(9) 0.0177(8) 0.0159(8) -0.0028(6) 0.0005(6) 0.0006(7) N20 0.0250(8) 0.0184(8) 0.0247(8) -0.0021(6) 0.0012(6) 0.0028(6) O21 0.0223(7) 0.0251(8) 0.0486(10) 0.0006(6) 0.0074(6) 0.0018(6) O22 0.0372(8) 0.0158(7) 0.0408(9) -0.0018(6) 0.0079(6) 0.0025(6) C23 0.0250(9) 0.0190(9) 0.0167(8) -0.0003(6) -0.0002(7) -0.0042(7) C24 0.0201(8) 0.0240(9) 0.0138(8) -0.0009(6) 0.0018(6) -0.0067(7) N25 0.0245(8) 0.0272(9) 0.0192(8) 0.0015(6) 0.0038(6) -0.0075(7) O26 0.0383(9) 0.0257(8) 0.0410(9) 0.0041(6) 0.0115(7) -0.0111(6) O27 0.0228(7) 0.0347(8) 0.0286(7) 0.0017(6) 0.0071(6) -0.0041(6) C28 0.0182(8) 0.0217(9) 0.0151(8) -0.0017(6) 0.0017(6) -0.0005(7) S29 0.0178(2) 0.0197(2) 0.0174(2) 0.00338(15) 0.00072(16) -0.00140(16) O30 0.0193(6) 0.0269(7) 0.0286(7) 0.0079(6) -0.0011(5) 0.0014(5) O31 0.0279(7) 0.0246(7) 0.0182(6) -0.0007(5) 0.0020(5) -0.0049(5) C32 0.0190(8) 0.0204(9) 0.0176(8) 0.0055(7) 0.0006(6) -0.0024(7) C33 0.0264(9) 0.0197(10) 0.0201(9) 0.0008(7) 0.0038(7) 0.0004(7) C34 0.0227(9) 0.0284(10) 0.0238(9) 0.0016(8) 0.0056(7) -0.0009(8) C35 0.0229(9) 0.0243(9) 0.0224(9) 0.0054(7) -0.0007(7) -0.0053(7) C36 0.0304(11) 0.0298(11) 0.0375(13) 0.0054(9) 0.0045(9) -0.0102(9) C37 0.0285(10) 0.0183(9) 0.0301(10) 0.0038(7) -0.0007(8) -0.0002(7) C38 0.0214(9) 0.0207(9) 0.0267(10) 0.0058(7) 0.0041(7) 0.0036(7) Cl39 0.0386(3) 0.0398(4) 0.0841(5) -0.0241(3) 0.0102(3) -0.0009(3) C40 0.0504(15) 0.0374(13) 0.0459(15) -0.0062(11) 0.0102(12) 0.0079(11) Cl41 0.0485(4) 0.0434(3) 0.0358(3) 0.0048(2) 0.0026(2) 0.0086(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 C1 C2 1.506(3) . ? C1 H42 1.03(3) . ? C1 H43 1.04(3) . ? C1 H44 0.92(3) . ? C2 C9 1.334(3) . ? C2 C3 1.518(3) . ? C3 C4 1.508(3) . ? C3 H45 1.03(2) . ? C3 H46 0.97(2) . ? C4 C5 1.320(3) . ? C4 H47 0.93(3) . ? C5 C6 1.505(3) . ? C5 H48 0.97(3) . ? C6 C7 1.553(3) . ? C6 H49 0.95(3) . ? C6 H50 0.85(3) . ? C7 C8 1.547(2) . ? C7 H51 0.93(2) . ? C7 H52 0.97(3) . ? C8 C9 1.518(2) . ? C8 C12 1.549(2) . ? C8 H53 0.99(2) . ? C9 C10 1.511(3) . ? C10 N11 1.474(2) . ? C10 H54 0.88(2) . ? C10 H55 0.98(2) . ? N11 C12 1.482(2) . ? N11 S29 1.6187(15) . ? C12 C13 1.510(2) . ? C12 H56 1.01(2) . ? C13 O14 1.457(2) . ? C13 H57 0.95(2) . ? C13 H58 0.93(2) . ? O14 C15 1.333(2) . ? C15 O16 1.207(2) . ? C15 C17 1.501(2) . ? C17 C18 1.387(2) . ? C17 C28 1.395(2) . ? C18 C19 1.386(3) . ? C18 H59 0.87(3) . ? C19 C23 1.383(3) . ? C19 N20 1.468(2) . ? N20 O21 1.226(2) . ? N20 O22 1.226(2) . ? C23 C24 1.381(3) . ? C23 H60 0.99(3) . ? C24 C28 1.381(3) . ? C24 N25 1.478(2) . ? N25 O26 1.220(2) . ? N25 O27 1.230(2) . ? C28 H61 0.89(2) . ? S29 O30 1.4369(14) . ? S29 O31 1.4375(14) . ? S29 C32 1.7650(18) . ? C32 C33 1.392(3) . ? C32 C38 1.392(3) . ? C33 C34 1.384(3) . ? C33 H62 0.76(3) . ? C34 C35 1.396(3) . ? C34 H63 0.98(3) . ? C35 C37 1.400(3) . ? C35 C36 1.508(3) . ? C36 H64 1.07(4) . ? C36 H65 0.93(3) . ? C36 H66 1.04(4) . ? C37 C38 1.385(3) . ? C37 H67 0.92(3) . ? C38 H68 0.86(3) . ? Cl39 C40 1.759(3) . ? C40 Cl41 1.758(3) . ? C40 H69 1.00(4) . ? C40 H70 0.88(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H42 106.8(17) . . ? C2 C1 H43 108.5(16) . . ? H42 C1 H43 111(2) . . ? C2 C1 H44 114.2(16) . . ? H42 C1 H44 109(2) . . ? H43 C1 H44 107(2) . . ? C9 C2 C1 123.41(17) . . ? C9 C2 C3 121.03(17) . . ? C1 C2 C3 115.21(16) . . ? C4 C3 C2 109.32(16) . . ? C4 C3 H45 109.0(13) . . ? C2 C3 H45 110.9(14) . . ? C4 C3 H46 106.6(14) . . ? C2 C3 H46 108.1(14) . . ? H45 C3 H46 112.9(19) . . ? C5 C4 C3 124.22(19) . . ? C5 C4 H47 116.5(16) . . ? C3 C4 H47 119.3(16) . . ? C4 C5 C6 126.2(2) . . ? C4 C5 H48 116.9(17) . . ? C6 C5 H48 116.7(17) . . ? C5 C6 C7 116.31(18) . . ? C5 C6 H49 109.8(15) . . ? C7 C6 H49 108.4(14) . . ? C5 C6 H50 105.8(19) . . ? C7 C6 H50 111.8(19) . . ? H49 C6 H50 104(2) . . ? C8 C7 C6 115.53(17) . . ? C8 C7 H51 105.4(14) . . ? C6 C7 H51 107.9(14) . . ? C8 C7 H52 105.5(15) . . ? C6 C7 H52 110.6(15) . . ? H51 C7 H52 112(2) . . ? C9 C8 C7 114.11(15) . . ? C9 C8 C12 104.10(14) . . ? C7 C8 C12 110.85(15) . . ? C9 C8 H53 106.6(12) . . ? C7 C8 H53 110.9(12) . . ? C12 C8 H53 110.0(12) . . ? C2 C9 C10 124.22(16) . . ? C2 C9 C8 126.33(17) . . ? C10 C9 C8 109.36(15) . . ? N11 C10 C9 104.26(14) . . ? N11 C10 H54 107.7(15) . . ? C9 C10 H54 110.8(15) . . ? N11 C10 H55 110.1(13) . . ? C9 C10 H55 112.6(13) . . ? H54 C10 H55 111(2) . . ? C10 N11 C12 112.62(14) . . ? C10 N11 S29 119.93(12) . . ? C12 N11 S29 119.97(12) . . ? N11 C12 C13 110.51(14) . . ? N11 C12 C8 104.74(13) . . ? C13 C12 C8 114.81(15) . . ? N11 C12 H56 111.0(12) . . ? C13 C12 H56 105.0(12) . . ? C8 C12 H56 110.9(12) . . ? O14 C13 C12 107.69(14) . . ? O14 C13 H57 109.7(13) . . ? C12 C13 H57 107.7(13) . . ? O14 C13 H58 107.1(13) . . ? C12 C13 H58 110.4(13) . . ? H57 C13 H58 114.0(18) . . ? C15 O14 C13 114.88(13) . . ? O16 C15 O14 124.90(16) . . ? O16 C15 C17 123.19(16) . . ? O14 C15 C17 111.91(15) . . ? C18 C17 C28 120.46(17) . . ? C18 C17 C15 122.24(16) . . ? C28 C17 C15 117.30(16) . . ? C17 C18 C19 118.25(17) . . ? C17 C18 H59 124.2(16) . . ? C19 C18 H59 117.6(16) . . ? C23 C19 C18 123.16(17) . . ? C23 C19 N20 117.58(16) . . ? C18 C19 N20 119.17(16) . . ? O21 N20 O22 124.45(16) . . ? O21 N20 C19 118.03(15) . . ? O22 N20 C19 117.50(16) . . ? C24 C23 C19 116.57(17) . . ? C24 C23 H60 121.3(14) . . ? C19 C23 H60 122.1(14) . . ? C28 C24 C23 122.88(17) . . ? C28 C24 N25 119.09(17) . . ? C23 C24 N25 118.02(16) . . ? O26 N25 O27 124.55(16) . . ? O26 N25 C24 117.93(16) . . ? O27 N25 C24 117.53(16) . . ? C24 C28 C17 118.67(17) . . ? C24 C28 H61 121.2(15) . . ? C17 C28 H61 120.1(15) . . ? O30 S29 O31 120.46(9) . . ? O30 S29 N11 106.83(8) . . ? O31 S29 N11 106.21(8) . . ? O30 S29 C32 107.41(8) . . ? O31 S29 C32 107.11(9) . . ? N11 S29 C32 108.37(8) . . ? C33 C32 C38 120.38(17) . . ? C33 C32 S29 119.93(15) . . ? C38 C32 S29 119.69(14) . . ? C34 C33 C32 119.46(19) . . ? C34 C33 H62 122.0(19) . . ? C32 C33 H62 118.4(19) . . ? C33 C34 C35 121.26(18) . . ? C33 C34 H63 120.9(15) . . ? C35 C34 H63 117.8(15) . . ? C34 C35 C37 118.29(17) . . ? C34 C35 C36 120.37(19) . . ? C37 C35 C36 121.33(19) . . ? C35 C36 H64 116(2) . . ? C35 C36 H65 111.4(18) . . ? H64 C36 H65 98(3) . . ? C35 C36 H66 109.5(19) . . ? H64 C36 H66 110(3) . . ? H65 C36 H66 111(3) . . ? C38 C37 C35 121.07(19) . . ? C38 C37 H67 114.8(15) . . ? C35 C37 H67 123.9(15) . . ? C37 C38 C32 119.49(18) . . ? C37 C38 H68 123.5(17) . . ? C32 C38 H68 116.8(17) . . ? Cl41 C40 Cl39 112.95(15) . . ? Cl41 C40 H69 107(2) . . ? Cl39 C40 H69 110(2) . . ? Cl41 C40 H70 110(2) . . ? Cl39 C40 H70 99(2) . . ? H69 C40 H70 118(3) . . ? 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 C9 C2 C3 C4 -84.7(2) . . . . ? C1 C2 C3 C4 88.6(2) . . . . ? C2 C3 C4 C5 86.9(2) . . . . ? C3 C4 C5 C6 1.5(3) . . . . ? C4 C5 C6 C7 -70.9(3) . . . . ? C5 C6 C7 C8 81.7(2) . . . . ? C6 C7 C8 C9 -84.7(2) . . . . ? C6 C7 C8 C12 158.19(16) . . . . ? C1 C2 C9 C10 -1.9(3) . . . . ? C3 C2 C9 C10 170.96(17) . . . . ? C1 C2 C9 C8 -178.18(17) . . . . ? C3 C2 C9 C8 -5.4(3) . . . . ? C7 C8 C9 C2 77.6(2) . . . . ? C12 C8 C9 C2 -161.41(18) . . . . ? C7 C8 C9 C10 -99.16(18) . . . . ? C12 C8 C9 C10 21.80(19) . . . . ? C2 C9 C10 N11 169.41(17) . . . . ? C8 C9 C10 N11 -13.72(19) . . . . ? C9 C10 N11 C12 -0.35(19) . . . . ? C9 C10 N11 S29 149.47(13) . . . . ? C10 N11 C12 C13 -110.52(16) . . . . ? S29 N11 C12 C13 99.67(15) . . . . ? C10 N11 C12 C8 13.65(19) . . . . ? S29 N11 C12 C8 -136.16(13) . . . . ? C9 C8 C12 N11 -20.96(17) . . . . ? C7 C8 C12 N11 102.16(16) . . . . ? C9 C8 C12 C13 100.42(17) . . . . ? C7 C8 C12 C13 -136.46(16) . . . . ? N11 C12 C13 O14 57.24(18) . . . . ? C8 C12 C13 O14 -60.93(19) . . . . ? C12 C13 O14 C15 177.42(14) . . . . ? C13 O14 C15 O16 -2.6(2) . . . . ? C13 O14 C15 C17 177.82(14) . . . . ? O16 C15 C17 C18 -178.21(17) . . . . ? O14 C15 C17 C18 1.4(2) . . . . ? O16 C15 C17 C28 1.5(3) . . . . ? O14 C15 C17 C28 -178.85(15) . . . . ? C28 C17 C18 C19 0.8(3) . . . . ? C15 C17 C18 C19 -179.48(16) . . . . ? C17 C18 C19 C23 -0.3(3) . . . . ? C17 C18 C19 N20 -176.84(15) . . . . ? C23 C19 N20 O21 -170.79(17) . . . . ? C18 C19 N20 O21 6.0(2) . . . . ? C23 C19 N20 O22 7.6(2) . . . . ? C18 C19 N20 O22 -175.64(17) . . . . ? C18 C19 C23 C24 -0.6(3) . . . . ? N20 C19 C23 C24 176.01(15) . . . . ? C19 C23 C24 C28 1.0(3) . . . . ? C19 C23 C24 N25 -177.51(15) . . . . ? C28 C24 N25 O26 -179.53(17) . . . . ? C23 C24 N25 O26 -0.9(2) . . . . ? C28 C24 N25 O27 0.2(2) . . . . ? C23 C24 N25 O27 178.74(16) . . . . ? C23 C24 C28 C17 -0.5(3) . . . . ? N25 C24 C28 C17 177.98(15) . . . . ? C18 C17 C28 C24 -0.4(3) . . . . ? C15 C17 C28 C24 179.86(15) . . . . ? C10 N11 S29 O30 168.15(13) . . . . ? C12 N11 S29 O30 -44.24(15) . . . . ? C10 N11 S29 O31 38.40(15) . . . . ? C12 N11 S29 O31 -173.98(12) . . . . ? C10 N11 S29 C32 -76.39(15) . . . . ? C12 N11 S29 C32 71.22(14) . . . . ? O30 S29 C32 C33 -154.60(15) . . . . ? O31 S29 C32 C33 -23.88(17) . . . . ? N11 S29 C32 C33 90.32(16) . . . . ? O30 S29 C32 C38 24.98(17) . . . . ? O31 S29 C32 C38 155.70(15) . . . . ? N11 S29 C32 C38 -90.10(16) . . . . ? C38 C32 C33 C34 -1.3(3) . . . . ? S29 C32 C33 C34 178.32(15) . . . . ? C32 C33 C34 C35 -0.5(3) . . . . ? C33 C34 C35 C37 2.2(3) . . . . ? C33 C34 C35 C36 -176.46(19) . . . . ? C34 C35 C37 C38 -2.3(3) . . . . ? C36 C35 C37 C38 176.41(19) . . . . ? C35 C37 C38 C32 0.6(3) . . . . ? C33 C32 C38 C37 1.2(3) . . . . ? S29 C32 C38 C37 -178.36(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.687 _refine_diff_density_min -0.838 _refine_diff_density_rms 0.096 data_03228 _database_code_depnum_ccdc_archive 'CCDC 249421' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H31 N3 O8 S' _chemical_formula_weight 617.66 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.3244(14) _cell_length_b 7.2183(8) _cell_length_c 30.905(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.270(3) _cell_angle_gamma 90.00 _cell_volume 2924.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 911 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 26.25 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 0.169 _exptl_absorpt_correction_type none _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_details ' 0.30 degree frames measured for 15.17 seconds each' _diffrn_measurement_method '\w scans' _diffrn_measurement_device 'three-circle goniometer with fixed chi' _diffrn_measurement_device_type 'Bruker Platform goniometer' _diffrn_detector 'CCD area detector' _diffrn_detector_type 'Bruker SMART 6000' _diffrn_detector_area_resol_mean 44.52 _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 42574 _diffrn_reflns_av_R_equivalents 0.1049 _diffrn_reflns_av_sigmaI/netI 0.0614 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 27.57 _reflns_number_total 6773 _reflns_number_gt 4921 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1999)' _computing_cell_refinement 'SAINT (Bruker, 1999)' _computing_data_reduction ; SAINT (Bruker, 1999), XTEL _computing_structure_solution SHELXS-97 (Sheldrick, 1990) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0607P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6773 _refine_ls_number_parameters 521 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0594 _refine_ls_R_factor_gt 0.0405 _refine_ls_wR_factor_ref 0.1045 _refine_ls_wR_factor_gt 0.0983 _refine_ls_goodness_of_fit_ref 0.928 _refine_ls_restrained_S_all 0.928 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.06752(17) 0.2940(2) 0.06664(7) 0.0331(4) Uani 1 1 d . . . C2 C -0.09002(12) 0.4980(2) 0.05729(5) 0.0192(3) Uani 1 1 d . . . N3 N -0.05701(10) 0.61367(17) 0.09797(4) 0.0187(3) Uani 1 1 d . . . C4 C -0.13433(12) 0.7592(2) 0.10082(5) 0.0179(3) Uani 1 1 d . . . C5 C -0.23111(12) 0.67478(19) 0.07691(5) 0.0165(3) Uani 1 1 d . . . C6 C -0.32344(12) 0.7194(2) 0.08429(5) 0.0165(3) Uani 1 1 d . . . C7 C -0.41951(12) 0.6347(2) 0.05861(5) 0.0204(3) Uani 1 1 d . . . C8 C -0.45656(12) 0.7497(2) 0.01840(5) 0.0208(3) Uani 1 1 d . . . C9 C -0.41956(12) 0.7322(2) -0.01852(5) 0.0206(3) Uani 1 1 d . . . C10 C -0.34374(12) 0.5875(2) -0.02720(5) 0.0195(3) Uani 1 1 d . . . C11 C -0.23068(12) 0.6093(2) -0.00512(5) 0.0168(3) Uani 1 1 d . . . C12 C -0.20490(12) 0.5390(2) 0.04315(5) 0.0160(3) Uani 1 1 d . . . S13 S 0.06054(3) 0.69347(6) 0.104305(13) 0.02180(11) Uani 1 1 d . . . O14 O 0.12594(9) 0.53941(18) 0.10012(4) 0.0323(3) Uani 1 1 d . . . O15 O 0.06619(9) 0.85292(17) 0.07703(4) 0.0301(3) Uani 1 1 d . . . C16 C 0.08089(12) 0.7686(2) 0.15932(5) 0.0224(3) Uani 1 1 d . . . C17 C 0.11994(13) 0.6452(3) 0.19255(6) 0.0293(4) Uani 1 1 d . . . C18 C 0.13566(15) 0.7041(3) 0.23583(6) 0.0383(5) Uani 1 1 d . . . C19 C 0.11125(14) 0.8830(3) 0.24678(6) 0.0416(5) Uani 1 1 d . . . C20 C 0.07279(14) 1.0051(3) 0.21309(7) 0.0385(5) Uani 1 1 d . . . C21 C 0.05805(13) 0.9504(3) 0.16945(6) 0.0291(4) Uani 1 1 d . . . C22 C 0.1275(2) 0.9457(6) 0.29412(8) 0.0682(9) Uani 1 1 d . . . C23 C -0.33805(11) 0.8739(2) 0.11481(5) 0.0180(3) Uani 1 1 d . . . C24 C -0.36210(14) 0.8397(2) 0.15580(6) 0.0262(4) Uani 1 1 d . . . C25 C -0.37650(15) 0.9842(3) 0.18355(6) 0.0321(4) Uani 1 1 d . . . C26 C -0.36880(15) 1.1655(3) 0.17015(6) 0.0338(4) Uani 1 1 d . . . C27 C -0.34448(18) 1.2015(3) 0.12946(6) 0.0409(5) Uani 1 1 d . . . C28 C -0.32951(16) 1.0569(2) 0.10169(6) 0.0319(4) Uani 1 1 d . . . C29 C -0.19505(13) 0.8087(2) -0.00769(5) 0.0183(3) Uani 1 1 d . . . O30 O -0.22288(9) 0.86718(14) -0.05321(3) 0.0196(2) Uani 1 1 d . . . C31 C -0.26334(12) 1.0359(2) -0.06019(5) 0.0178(3) Uani 1 1 d . . . O32 O -0.27339(9) 1.14675(15) -0.03219(4) 0.0256(3) Uani 1 1 d . . . C33 C -0.29882(12) 1.0704(2) -0.10819(5) 0.0179(3) Uani 1 1 d . . . C34 C -0.34370(12) 1.2411(2) -0.12026(5) 0.0191(3) Uani 1 1 d . . . C35 C -0.37712(12) 1.2777(2) -0.16415(5) 0.0198(3) Uani 1 1 d . . . N36 N -0.42461(11) 1.45918(19) -0.17659(5) 0.0251(3) Uani 1 1 d . . . O37 O -0.45617(10) 1.48854(18) -0.21570(4) 0.0354(3) Uani 1 1 d . . . O38 O -0.42965(11) 1.57031(17) -0.14725(4) 0.0359(3) Uani 1 1 d . . . C39 C -0.36695(12) 1.1536(2) -0.19701(5) 0.0215(3) Uani 1 1 d . . . C40 C -0.32112(12) 0.9860(2) -0.18359(5) 0.0210(3) Uani 1 1 d . . . N41 N -0.30491(11) 0.8544(2) -0.21803(5) 0.0273(3) Uani 1 1 d . . . O42 O -0.32988(12) 0.90244(19) -0.25624(4) 0.0407(4) Uani 1 1 d . . . O43 O -0.26571(11) 0.70502(17) -0.20641(4) 0.0340(3) Uani 1 1 d . . . C44 C -0.28705(12) 0.9402(2) -0.14005(5) 0.0194(3) Uani 1 1 d . . . H45 H -0.1074(16) 0.252(3) 0.0883(7) 0.036(6) Uiso 1 1 d . . . H46 H 0.0049(17) 0.268(3) 0.0750(7) 0.036(6) Uiso 1 1 d . . . H47 H -0.0914(17) 0.225(3) 0.0393(7) 0.042(6) Uiso 1 1 d . . . H48 H -0.0531(13) 0.534(2) 0.0345(6) 0.020(4) Uiso 1 1 d . . . H49 H -0.1185(14) 0.877(3) 0.0861(6) 0.025(5) Uiso 1 1 d . . . H50 H -0.1396(13) 0.783(2) 0.1306(6) 0.016(4) Uiso 1 1 d . . . H51 H -0.4728(14) 0.628(3) 0.0770(6) 0.026(5) Uiso 1 1 d . . . H52 H -0.4043(13) 0.507(3) 0.0486(5) 0.021(4) Uiso 1 1 d . . . H53 H -0.5058(14) 0.844(3) 0.0217(6) 0.027(5) Uiso 1 1 d . . . H54 H -0.4483(14) 0.815(3) -0.0424(6) 0.028(5) Uiso 1 1 d . . . H55 H -0.3445(13) 0.590(2) -0.0591(6) 0.017(4) Uiso 1 1 d . . . H56 H -0.3617(13) 0.468(3) -0.0187(6) 0.024(5) Uiso 1 1 d . . . H57 H -0.1914(13) 0.532(2) -0.0219(5) 0.014(4) Uiso 1 1 d . . . H58 H -0.2436(13) 0.428(2) 0.0446(5) 0.018(4) Uiso 1 1 d . . . H59 H 0.1344(16) 0.520(3) 0.1855(6) 0.037(6) Uiso 1 1 d . . . H60 H 0.1614(16) 0.618(3) 0.2596(7) 0.040(6) Uiso 1 1 d . . . H61 H 0.0562(17) 1.135(3) 0.2202(7) 0.053(7) Uiso 1 1 d . . . H62 H 0.0329(15) 1.035(3) 0.1463(7) 0.034(5) Uiso 1 1 d . . . H63 H 0.076(3) 0.968(5) 0.3039(10) 0.086(10) Uiso 1 1 d . . . H64 H 0.189(3) 1.002(5) 0.3026(10) 0.093(11) Uiso 1 1 d . . . H65 H 0.171(5) 0.836(8) 0.3166(19) 0.22(2) Uiso 1 1 d . . . H66 H -0.3709(15) 0.717(3) 0.1642(6) 0.032(5) Uiso 1 1 d . . . H67 H -0.3888(19) 0.964(3) 0.2096(8) 0.054(7) Uiso 1 1 d . . . H68 H -0.3809(17) 1.265(3) 0.1891(7) 0.043(6) Uiso 1 1 d . . . H69 H -0.3412(17) 1.319(3) 0.1185(8) 0.052(7) Uiso 1 1 d . . . H70 H -0.3163(15) 1.085(3) 0.0715(7) 0.039(6) Uiso 1 1 d . . . H71 H -0.1222(14) 0.820(2) 0.0006(6) 0.020(4) Uiso 1 1 d . . . H72 H -0.2313(12) 0.886(2) 0.0097(5) 0.012(4) Uiso 1 1 d . . . H73 H -0.3489(12) 1.331(2) -0.0992(6) 0.016(4) Uiso 1 1 d . . . H74 H -0.3917(14) 1.185(2) -0.2273(6) 0.025(5) Uiso 1 1 d . . . H75 H -0.2551(13) 0.828(3) -0.1325(6) 0.020(4) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0341(11) 0.0153(8) 0.0453(12) -0.0030(8) -0.0052(9) 0.0068(7) C2 0.0217(8) 0.0158(7) 0.0194(8) -0.0019(6) 0.0020(6) 0.0018(6) N3 0.0188(7) 0.0160(6) 0.0209(7) -0.0026(5) 0.0026(5) 0.0001(5) C4 0.0199(8) 0.0148(7) 0.0185(8) -0.0021(6) 0.0027(6) 0.0007(6) C5 0.0225(8) 0.0121(7) 0.0145(7) 0.0025(5) 0.0018(6) -0.0017(6) C6 0.0221(8) 0.0127(7) 0.0145(7) 0.0027(5) 0.0026(6) -0.0018(6) C7 0.0208(8) 0.0169(8) 0.0239(8) -0.0014(6) 0.0050(7) -0.0028(6) C8 0.0172(8) 0.0162(7) 0.0273(9) -0.0020(6) -0.0002(6) -0.0019(6) C9 0.0215(8) 0.0148(7) 0.0228(8) -0.0004(6) -0.0035(6) -0.0021(6) C10 0.0254(9) 0.0137(7) 0.0180(8) -0.0017(6) 0.0007(6) -0.0021(6) C11 0.0215(8) 0.0115(7) 0.0173(8) -0.0019(6) 0.0034(6) 0.0009(6) C12 0.0201(8) 0.0106(7) 0.0172(7) -0.0004(5) 0.0031(6) -0.0005(6) S13 0.0183(2) 0.0243(2) 0.0230(2) -0.00319(16) 0.00411(15) -0.00128(15) O14 0.0219(6) 0.0349(7) 0.0404(8) -0.0117(6) 0.0068(5) 0.0043(5) O15 0.0282(7) 0.0350(7) 0.0272(7) 0.0042(5) 0.0053(5) -0.0092(5) C16 0.0157(8) 0.0278(9) 0.0229(8) -0.0027(6) 0.0013(6) -0.0008(6) C17 0.0227(9) 0.0347(10) 0.0295(10) 0.0016(8) 0.0019(7) 0.0011(7) C18 0.0246(10) 0.0615(14) 0.0275(10) 0.0074(9) 0.0017(8) 0.0001(9) C19 0.0224(10) 0.0742(15) 0.0282(10) -0.0157(10) 0.0046(8) -0.0020(9) C20 0.0249(10) 0.0468(12) 0.0430(12) -0.0207(9) 0.0040(8) 0.0016(8) C21 0.0210(9) 0.0318(10) 0.0330(10) -0.0077(8) 0.0012(7) 0.0014(7) C22 0.0351(14) 0.135(3) 0.0339(13) -0.0328(16) 0.0041(11) 0.0023(16) C23 0.0172(8) 0.0186(7) 0.0177(8) -0.0014(6) 0.0015(6) 0.0015(6) C24 0.0324(10) 0.0257(9) 0.0218(9) 0.0006(7) 0.0082(7) -0.0047(7) C25 0.0366(11) 0.0401(11) 0.0215(9) -0.0046(8) 0.0098(8) 0.0003(8) C26 0.0422(11) 0.0315(10) 0.0255(9) -0.0084(8) 0.0006(8) 0.0164(8) C27 0.0743(16) 0.0190(9) 0.0282(10) 0.0011(7) 0.0059(10) 0.0129(9) C28 0.0563(13) 0.0197(8) 0.0208(9) 0.0023(7) 0.0096(8) 0.0053(8) C29 0.0251(9) 0.0143(7) 0.0151(7) 0.0017(6) 0.0024(6) -0.0017(6) O30 0.0305(6) 0.0131(5) 0.0155(5) 0.0021(4) 0.0045(4) 0.0021(4) C31 0.0201(8) 0.0137(7) 0.0200(8) 0.0010(6) 0.0048(6) -0.0008(6) O32 0.0398(7) 0.0182(6) 0.0188(6) -0.0009(4) 0.0054(5) 0.0044(5) C33 0.0184(8) 0.0170(7) 0.0185(8) 0.0008(6) 0.0042(6) -0.0007(6) C34 0.0200(8) 0.0175(7) 0.0208(8) -0.0013(6) 0.0060(6) -0.0006(6) C35 0.0189(8) 0.0177(8) 0.0229(8) 0.0037(6) 0.0036(6) 0.0025(6) N36 0.0265(8) 0.0242(7) 0.0244(8) 0.0059(6) 0.0039(6) 0.0057(6) O37 0.0411(8) 0.0362(7) 0.0267(7) 0.0096(6) -0.0001(6) 0.0106(6) O38 0.0511(9) 0.0262(7) 0.0301(7) 0.0006(5) 0.0064(6) 0.0160(6) C39 0.0218(8) 0.0246(8) 0.0181(8) 0.0006(6) 0.0032(6) -0.0001(6) C40 0.0232(8) 0.0203(8) 0.0193(8) -0.0041(6) 0.0036(6) -0.0008(6) N41 0.0312(8) 0.0269(8) 0.0226(8) -0.0051(6) 0.0020(6) 0.0016(6) O42 0.0613(10) 0.0410(8) 0.0177(7) -0.0051(5) 0.0008(6) 0.0121(7) O43 0.0476(8) 0.0239(6) 0.0294(7) -0.0060(5) 0.0039(6) 0.0092(6) C44 0.0210(8) 0.0164(8) 0.0208(8) 0.0001(6) 0.0042(6) -0.0004(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 C1 C2 1.520(2) . ? C1 H45 0.97(2) . ? C1 H46 0.97(2) . ? C1 H47 0.99(2) . ? C2 N3 1.5079(19) . ? C2 C12 1.544(2) . ? C2 H48 0.965(18) . ? N3 C4 1.4847(19) . ? N3 S13 1.6474(13) . ? C4 C5 1.497(2) . ? C4 H49 1.005(19) . ? C4 H50 0.952(17) . ? C5 C6 1.330(2) . ? C5 C12 1.517(2) . ? C6 C23 1.496(2) . ? C6 C7 1.510(2) . ? C7 C8 1.503(2) . ? C7 H51 0.986(19) . ? C7 H52 1.002(18) . ? C8 C9 1.327(2) . ? C8 H53 0.964(19) . ? C9 C10 1.510(2) . ? C9 H54 0.971(19) . ? C10 C11 1.547(2) . ? C10 H55 0.985(17) . ? C10 H56 0.944(19) . ? C11 C29 1.522(2) . ? C11 C12 1.555(2) . ? C11 H57 0.976(17) . ? C12 H58 0.958(17) . ? S13 O14 1.4328(12) . ? S13 O15 1.4365(12) . ? S13 C16 1.7591(17) . ? C16 C17 1.389(2) . ? C16 C21 1.395(2) . ? C17 C18 1.383(3) . ? C17 H59 0.96(2) . ? C18 C19 1.389(3) . ? C18 H60 0.97(2) . ? C19 C20 1.390(3) . ? C19 C22 1.510(3) . ? C20 C21 1.385(3) . ? C20 H61 1.00(2) . ? C21 H62 0.95(2) . ? C22 H63 0.82(3) . ? C22 H64 0.92(4) . ? C22 H65 1.14(6) . ? C23 C24 1.383(2) . ? C23 C28 1.392(2) . ? C24 C25 1.385(2) . ? C24 H66 0.94(2) . ? C25 C26 1.382(3) . ? C25 H67 0.86(2) . ? C26 C27 1.378(3) . ? C26 H68 0.96(2) . ? C27 C28 1.388(3) . ? C27 H69 0.92(2) . ? C28 H70 1.00(2) . ? C29 O30 1.4523(18) . ? C29 H71 0.963(18) . ? C29 H72 0.961(17) . ? O30 C31 1.3336(18) . ? C31 O32 1.2034(18) . ? C31 C33 1.495(2) . ? C33 C44 1.390(2) . ? C33 C34 1.391(2) . ? C34 C35 1.376(2) . ? C34 H73 0.933(17) . ? C35 C39 1.379(2) . ? C35 N36 1.4757(19) . ? N36 O38 1.2216(18) . ? N36 O37 1.2255(18) . ? C39 C40 1.385(2) . ? C39 H74 0.962(18) . ? C40 C44 1.382(2) . ? C40 N41 1.471(2) . ? N41 O42 1.2187(18) . ? N41 O43 1.2237(18) . ? C44 H75 0.923(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 H45 108.8(12) . . ? C2 C1 H46 112.9(12) . . ? H45 C1 H46 113.3(17) . . ? C2 C1 H47 107.9(12) . . ? H45 C1 H47 107.2(17) . . ? H46 C1 H47 106.4(17) . . ? N3 C2 C1 111.07(14) . . ? N3 C2 C12 104.88(12) . . ? C1 C2 C12 113.05(14) . . ? N3 C2 H48 110.5(10) . . ? C1 C2 H48 106.9(10) . . ? C12 C2 H48 110.5(10) . . ? C4 N3 C2 109.80(12) . . ? C4 N3 S13 113.62(10) . . ? C2 N3 S13 114.99(10) . . ? N3 C4 C5 103.22(12) . . ? N3 C4 H49 111.6(10) . . ? C5 C4 H49 110.7(10) . . ? N3 C4 H50 111.0(10) . . ? C5 C4 H50 110.3(10) . . ? H49 C4 H50 109.8(14) . . ? C6 C5 C4 123.97(14) . . ? C6 C5 C12 127.42(14) . . ? C4 C5 C12 108.59(13) . . ? C5 C6 C23 121.12(13) . . ? C5 C6 C7 122.36(14) . . ? C23 C6 C7 116.10(13) . . ? C8 C7 C6 109.48(13) . . ? C8 C7 H51 109.9(11) . . ? C6 C7 H51 110.4(11) . . ? C8 C7 H52 107.8(10) . . ? C6 C7 H52 109.6(10) . . ? H51 C7 H52 109.6(14) . . ? C9 C8 C7 122.73(15) . . ? C9 C8 H53 121.6(11) . . ? C7 C8 H53 115.6(11) . . ? C8 C9 C10 125.55(15) . . ? C8 C9 H54 116.0(11) . . ? C10 C9 H54 118.3(11) . . ? C9 C10 C11 118.77(13) . . ? C9 C10 H55 106.3(10) . . ? C11 C10 H55 106.0(10) . . ? C9 C10 H56 111.8(11) . . ? C11 C10 H56 104.2(11) . . ? H55 C10 H56 109.5(14) . . ? C29 C11 C10 111.17(13) . . ? C29 C11 C12 109.92(12) . . ? C10 C11 C12 114.91(13) . . ? C29 C11 H57 108.2(10) . . ? C10 C11 H57 106.2(10) . . ? C12 C11 H57 106.0(9) . . ? C5 C12 C2 105.51(12) . . ? C5 C12 C11 114.26(12) . . ? C2 C12 C11 111.86(13) . . ? C5 C12 H58 108.5(10) . . ? C2 C12 H58 109.9(10) . . ? C11 C12 H58 106.8(10) . . ? O14 S13 O15 118.20(8) . . ? O14 S13 N3 107.37(7) . . ? O15 S13 N3 111.01(7) . . ? O14 S13 C16 109.59(8) . . ? O15 S13 C16 107.75(8) . . ? N3 S13 C16 101.67(7) . . ? C17 C16 C21 120.35(17) . . ? C17 C16 S13 119.32(13) . . ? C21 C16 S13 120.33(13) . . ? C18 C17 C16 119.35(19) . . ? C18 C17 H59 120.6(12) . . ? C16 C17 H59 120.1(12) . . ? C17 C18 C19 121.31(19) . . ? C17 C18 H60 120.4(13) . . ? C19 C18 H60 118.3(13) . . ? C18 C19 C20 118.57(18) . . ? C18 C19 C22 121.0(2) . . ? C20 C19 C22 120.4(2) . . ? C21 C20 C19 121.18(19) . . ? C21 C20 H61 118.9(13) . . ? C19 C20 H61 119.9(13) . . ? C20 C21 C16 119.20(19) . . ? C20 C21 H62 121.2(12) . . ? C16 C21 H62 119.6(12) . . ? C19 C22 H63 116(2) . . ? C19 C22 H64 112(2) . . ? H63 C22 H64 126(3) . . ? C19 C22 H65 111(3) . . ? H63 C22 H65 106(4) . . ? H64 C22 H65 79(3) . . ? C24 C23 C28 118.71(15) . . ? C24 C23 C6 121.45(14) . . ? C28 C23 C6 119.82(14) . . ? C23 C24 C25 120.85(16) . . ? C23 C24 H66 118.9(12) . . ? C25 C24 H66 120.2(12) . . ? C26 C25 C24 120.12(17) . . ? C26 C25 H67 118.3(16) . . ? C24 C25 H67 121.5(16) . . ? C27 C26 C25 119.60(17) . . ? C27 C26 H68 120.5(13) . . ? C25 C26 H68 119.9(13) . . ? C26 C27 C28 120.36(18) . . ? C26 C27 H69 123.1(15) . . ? C28 C27 H69 116.5(15) . . ? C27 C28 C23 120.34(17) . . ? C27 C28 H70 119.6(12) . . ? C23 C28 H70 120.0(12) . . ? O30 C29 C11 107.29(12) . . ? O30 C29 H71 107.7(10) . . ? C11 C29 H71 112.3(10) . . ? O30 C29 H72 107.9(9) . . ? C11 C29 H72 109.0(9) . . ? H71 C29 H72 112.5(14) . . ? C31 O30 C29 116.63(12) . . ? O32 C31 O30 125.77(14) . . ? O32 C31 C33 123.11(14) . . ? O30 C31 C33 111.09(12) . . ? C44 C33 C34 120.42(15) . . ? C44 C33 C31 122.29(14) . . ? C34 C33 C31 117.29(13) . . ? C35 C34 C33 118.85(14) . . ? C35 C34 H73 120.2(10) . . ? C33 C34 H73 120.9(10) . . ? C34 C35 C39 123.00(15) . . ? C34 C35 N36 118.40(14) . . ? C39 C35 N36 118.59(14) . . ? O38 N36 O37 124.34(14) . . ? O38 N36 C35 117.86(13) . . ? O37 N36 C35 117.80(14) . . ? C35 C39 C40 116.30(15) . . ? C35 C39 H74 120.0(11) . . ? C40 C39 H74 123.7(11) . . ? C44 C40 C39 123.46(15) . . ? C44 C40 N41 119.02(14) . . ? C39 C40 N41 117.48(14) . . ? O42 N41 O43 124.32(14) . . ? O42 N41 C40 117.86(14) . . ? O43 N41 C40 117.81(14) . . ? C40 C44 C33 117.97(15) . . ? C40 C44 H75 120.7(11) . . ? C33 C44 H75 121.3(11) . . ? 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 C1 C2 N3 C4 -139.49(15) . . . . ? C12 C2 N3 C4 -17.04(16) . . . . ? C1 C2 N3 S13 90.89(16) . . . . ? C12 C2 N3 S13 -146.66(10) . . . . ? C2 N3 C4 C5 27.56(15) . . . . ? S13 N3 C4 C5 157.92(10) . . . . ? N3 C4 C5 C6 154.10(14) . . . . ? N3 C4 C5 C12 -27.57(15) . . . . ? C4 C5 C6 C23 6.0(2) . . . . ? C12 C5 C6 C23 -172.00(13) . . . . ? C4 C5 C6 C7 178.35(14) . . . . ? C12 C5 C6 C7 0.3(2) . . . . ? C5 C6 C7 C8 -89.34(18) . . . . ? C23 C6 C7 C8 83.37(16) . . . . ? C6 C7 C8 C9 82.75(19) . . . . ? C7 C8 C9 C10 5.6(3) . . . . ? C8 C9 C10 C11 -74.8(2) . . . . ? C9 C10 C11 C29 -43.39(19) . . . . ? C9 C10 C11 C12 82.24(17) . . . . ? C6 C5 C12 C2 -164.13(15) . . . . ? C4 C5 C12 C2 17.61(15) . . . . ? C6 C5 C12 C11 72.57(19) . . . . ? C4 C5 C12 C11 -105.68(14) . . . . ? N3 C2 C12 C5 -0.50(15) . . . . ? C1 C2 C12 C5 120.65(15) . . . . ? N3 C2 C12 C11 124.30(13) . . . . ? C1 C2 C12 C11 -114.54(16) . . . . ? C29 C11 C12 C5 45.31(17) . . . . ? C10 C11 C12 C5 -80.97(16) . . . . ? C29 C11 C12 C2 -74.48(15) . . . . ? C10 C11 C12 C2 159.23(12) . . . . ? C4 N3 S13 O14 -179.14(11) . . . . ? C2 N3 S13 O14 -51.42(12) . . . . ? C4 N3 S13 O15 -48.56(13) . . . . ? C2 N3 S13 O15 79.16(12) . . . . ? C4 N3 S13 C16 65.81(12) . . . . ? C2 N3 S13 C16 -166.46(11) . . . . ? O14 S13 C16 C17 -24.24(16) . . . . ? O15 S13 C16 C17 -154.07(14) . . . . ? N3 S13 C16 C17 89.16(14) . . . . ? O14 S13 C16 C21 155.75(13) . . . . ? O15 S13 C16 C21 25.92(16) . . . . ? N3 S13 C16 C21 -90.85(14) . . . . ? C21 C16 C17 C18 0.2(3) . . . . ? S13 C16 C17 C18 -179.80(14) . . . . ? C16 C17 C18 C19 1.3(3) . . . . ? C17 C18 C19 C20 -1.7(3) . . . . ? C17 C18 C19 C22 179.3(2) . . . . ? C18 C19 C20 C21 0.5(3) . . . . ? C22 C19 C20 C21 179.5(2) . . . . ? C19 C20 C21 C16 1.0(3) . . . . ? C17 C16 C21 C20 -1.3(3) . . . . ? S13 C16 C21 C20 178.68(14) . . . . ? C5 C6 C23 C24 -107.25(18) . . . . ? C7 C6 C23 C24 79.95(19) . . . . ? C5 C6 C23 C28 74.1(2) . . . . ? C7 C6 C23 C28 -98.71(18) . . . . ? C28 C23 C24 C25 -0.6(3) . . . . ? C6 C23 C24 C25 -179.30(16) . . . . ? C23 C24 C25 C26 1.2(3) . . . . ? C24 C25 C26 C27 -1.5(3) . . . . ? C25 C26 C27 C28 1.1(3) . . . . ? C26 C27 C28 C23 -0.6(3) . . . . ? C24 C23 C28 C27 0.3(3) . . . . ? C6 C23 C28 C27 178.99(18) . . . . ? C10 C11 C29 O30 -50.57(16) . . . . ? C12 C11 C29 O30 -178.94(12) . . . . ? C11 C29 O30 C31 136.37(13) . . . . ? C29 O30 C31 O32 4.4(2) . . . . ? C29 O30 C31 C33 -173.79(12) . . . . ? O32 C31 C33 C44 -179.64(15) . . . . ? O30 C31 C33 C44 -1.4(2) . . . . ? O32 C31 C33 C34 1.2(2) . . . . ? O30 C31 C33 C34 179.43(13) . . . . ? C44 C33 C34 C35 0.7(2) . . . . ? C31 C33 C34 C35 179.93(14) . . . . ? C33 C34 C35 C39 -1.0(2) . . . . ? C33 C34 C35 N36 179.99(14) . . . . ? C34 C35 N36 O38 1.8(2) . . . . ? C39 C35 N36 O38 -177.30(15) . . . . ? C34 C35 N36 O37 -178.39(15) . . . . ? C39 C35 N36 O37 2.5(2) . . . . ? C34 C35 C39 C40 0.4(2) . . . . ? N36 C35 C39 C40 179.48(14) . . . . ? C35 C39 C40 C44 0.4(2) . . . . ? C35 C39 C40 N41 -177.21(14) . . . . ? C44 C40 N41 O42 -175.55(16) . . . . ? C39 C40 N41 O42 2.1(2) . . . . ? C44 C40 N41 O43 3.3(2) . . . . ? C39 C40 N41 O43 -179.05(15) . . . . ? C39 C40 C44 C33 -0.6(2) . . . . ? N41 C40 C44 C33 176.97(14) . . . . ? C34 C33 C44 C40 0.0(2) . . . . ? C31 C33 C44 C40 -179.16(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.57 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.519 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.054