# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge ? _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Organic & Biomolecular Chemistry' loop_ _publ_author_name 'Hideto Miyabe' 'Kayoko Fujii' 'Takeaki Naito' _publ_contact_author_name 'Prof Takeaki Naito ' _publ_contact_author_email 'taknaito@kobepharma-u.ac.jp ' _publ_section_title ; Radical Addition to Oxime Ethers for Asymmetric Synthesis of b-Amino Acid Derivatives ; data_sample1-98 _database_code_CSD 135458 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H32 N2 O4 S' _chemical_formula_weight 480.61 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.1034(11) _cell_length_b 11.9818(14) _cell_length_c 9.9624(12) _cell_angle_alpha 90.00 _cell_angle_beta 109.214(8) _cell_angle_gamma 90.00 _cell_volume 1251.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 25 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.275 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.165 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'nomal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R diffractometer' _diffrn_measurement_method ot _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 3246 _diffrn_reflns_av_R_equivalents 0.0131 _diffrn_reflns_av_sigmaI/netI 0.0174 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -3 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3012 _reflns_number_gt 2708 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/MSC AFC5R software 1992' _computing_cell_refinement 'Rigaku/MSC AFC5R software 1992' _computing_data_reduction 'Rigaku/MSC AFC5R software 1992' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.016(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(7) _refine_ls_number_reflns 3012 _refine_ls_number_parameters 308 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0377 _refine_ls_R_factor_gt 0.0297 _refine_ls_wR_factor_ref 0.1054 _refine_ls_wR_factor_gt 0.0971 _refine_ls_goodness_of_fit_ref 0.902 _refine_ls_restrained_S_all 0.902 _refine_ls_shift/su_max 0.025 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.12345(4) -0.65054(4) 0.09591(5) 0.03947(14) Uani 1 1 d . . . O1 O 0.16284(18) -0.53867(16) 0.0844(2) 0.0575(4) Uani 1 1 d . . . O2 O 0.20885(17) -0.7210(2) 0.2007(2) 0.0623(5) Uani 1 1 d . . . O3 O 0.15440(15) -0.84169(16) -0.1910(2) 0.0547(4) Uani 1 1 d . . . O4 O 0.5142(2) -0.6358(2) 0.1355(2) 0.0823(8) Uani 1 1 d . . . N1 N 0.08508(14) -0.71602(15) -0.06398(18) 0.0363(4) Uani 1 1 d . . . N2 N 0.51167(19) -0.7501(2) 0.1103(3) 0.0568(5) Uani 1 1 d . . . C1 C -0.04256(16) -0.76858(17) -0.1044(2) 0.0348(4) Uani 1 1 d . . . C2 C -0.1227(2) -0.7639(2) -0.2635(2) 0.0467(5) Uani 1 1 d . . . C3 C -0.2454(2) -0.7048(2) -0.2605(2) 0.0495(5) Uani 1 1 d . . . C4 C -0.3135(2) -0.7826(3) -0.1866(3) 0.0565(6) Uani 1 1 d . . . C5 C -0.2310(2) -0.7742(2) -0.0277(3) 0.0495(5) Uani 1 1 d . . . C6 C -0.12110(17) -0.69777(18) -0.0332(2) 0.0354(4) Uani 1 1 d . . . C7 C -0.1913(2) -0.6116(2) -0.1502(2) 0.0435(4) Uani 1 1 d . . . C8 C -0.1077(3) -0.5260(2) -0.1933(3) 0.0573(6) Uani 1 1 d . . . C9 C -0.2928(3) -0.5448(3) -0.1106(4) 0.0678(8) Uani 1 1 d . . . C10 C -0.03311(19) -0.6550(3) 0.1078(2) 0.0477(5) Uani 1 1 d . . . C11 C 0.17769(18) -0.76066(19) -0.1134(2) 0.0403(4) Uani 1 1 d . . . C12 C 0.30577(18) -0.6999(2) -0.0731(3) 0.0436(4) Uani 1 1 d . . . C13 C 0.4110(2) -0.7762(2) 0.0106(3) 0.0584(6) Uani 1 1 d . . . C14 C 0.6214(3) -0.6083(5) 0.2590(4) 0.1000(16) Uani 1 1 d . . . C15 C 0.5805(2) -0.5343(3) 0.3556(3) 0.0539(6) Uani 1 1 d . . . C16 C 0.6500(3) -0.4411(3) 0.4145(3) 0.0681(8) Uani 1 1 d . . . C17 C 0.6162(5) -0.3751(4) 0.5063(4) 0.0889(11) Uani 1 1 d . . . C18 C 0.5101(5) -0.3990(5) 0.5417(4) 0.0974(14) Uani 1 1 d . . . C19 C 0.4365(4) -0.4922(5) 0.4824(4) 0.0888(12) Uani 1 1 d . . . C20 C 0.4726(3) -0.5588(3) 0.3898(3) 0.0669(7) Uani 1 1 d . . . C21 C 0.3304(2) -0.6628(3) -0.2115(3) 0.0527(6) Uani 1 1 d . . . C22 C 0.2303(2) -0.5849(2) -0.3020(3) 0.0477(5) Uani 1 1 d . . . C23 C 0.1326(3) -0.6242(3) -0.4194(3) 0.0642(7) Uani 1 1 d . . . C24 C 0.0406(3) -0.5524(4) -0.5030(3) 0.0794(10) Uani 1 1 d . . . C25 C 0.0462(4) -0.4397(4) -0.4718(4) 0.0794(10) Uani 1 1 d . . . C26 C 0.1435(4) -0.4007(3) -0.3567(4) 0.0756(9) Uani 1 1 d . . . C27 C 0.2338(3) -0.4710(3) -0.2726(3) 0.0600(6) Uani 1 1 d . . . H1 H -0.0360 -0.8421 -0.0708 0.042 Uiso 1 1 d . . . H2 H -0.1412 -0.8362 -0.3026 0.055 Uiso 1 1 d . . . H3 H -0.0812 -0.7216 -0.3165 0.055 Uiso 1 1 d . . . H4 H -0.2974 -0.6778 -0.3509 0.058 Uiso 1 1 d . . . H5 H -0.3981 -0.7565 -0.2007 0.067 Uiso 1 1 d . . . H6 H -0.3161 -0.8561 -0.2201 0.067 Uiso 1 1 d . . . H7 H -0.2776 -0.7410 0.0264 0.060 Uiso 1 1 d . . . H8 H -0.2005 -0.8448 0.0091 0.060 Uiso 1 1 d . . . H9 H -0.1586 -0.4836 -0.2718 0.068 Uiso 1 1 d . . . H10 H -0.0434 -0.5644 -0.2192 0.068 Uiso 1 1 d . . . H11 H -0.0686 -0.4781 -0.1153 0.068 Uiso 1 1 d . . . H12 H -0.3408 -0.5007 -0.1914 0.083 Uiso 1 1 d . . . H13 H -0.3490 -0.5940 -0.0868 0.083 Uiso 1 1 d . . . H14 H -0.2529 -0.4966 -0.0340 0.083 Uiso 1 1 d . . . H15 H -0.0587 -0.5832 0.1260 0.056 Uiso 1 1 d . . . H16 H -0.0355 -0.7051 0.1810 0.056 Uiso 1 1 d . . . H17 H 0.3032 -0.6356 -0.0176 0.051 Uiso 1 1 d . . . H18 H 0.4004 -0.8519 -0.0139 0.069 Uiso 1 1 d . . . H19 H 0.6844 -0.5711 0.2290 0.117 Uiso 1 1 d . . . H20 H 0.6578 -0.6751 0.3075 0.117 Uiso 1 1 d . . . H21 H 0.7233 -0.4237 0.3909 0.078 Uiso 1 1 d . . . H22 H 0.6653 -0.3120 0.5495 0.106 Uiso 1 1 d . . . H23 H 0.4855 -0.3547 0.6065 0.114 Uiso 1 1 d . . . H24 H 0.3628 -0.5094 0.5042 0.101 Uiso 1 1 d . . . H25 H 0.4238 -0.6221 0.3508 0.079 Uiso 1 1 d . . . H26 H 0.3331 -0.7280 -0.2644 0.062 Uiso 1 1 d . . . H27 H 0.4111 -0.6265 -0.1846 0.062 Uiso 1 1 d . . . H28 H 0.1298 -0.7008 -0.4423 0.076 Uiso 1 1 d . . . H29 H -0.0265 -0.5802 -0.5821 0.095 Uiso 1 1 d . . . H30 H -0.0150 -0.3907 -0.5291 0.094 Uiso 1 1 d . . . H31 H 0.1463 -0.3232 -0.3353 0.088 Uiso 1 1 d . . . H32 H 0.3003 -0.4425 -0.1937 0.071 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 S1 0.0338(2) 0.0425(2) 0.0386(2) -0.0032(2) 0.00725(16) -0.0036(2) O1 0.0599(10) 0.0430(9) 0.0726(11) -0.0135(8) 0.0257(8) -0.0132(8) O2 0.0513(9) 0.0760(14) 0.0463(9) 0.0088(9) -0.0022(7) 0.0037(9) O3 0.0412(8) 0.0511(9) 0.0754(12) -0.0185(8) 0.0240(8) -0.0004(7) O4 0.0606(11) 0.0855(17) 0.0733(12) -0.0297(13) -0.0155(9) 0.0214(12) N1 0.0268(7) 0.0397(9) 0.0422(8) -0.0045(7) 0.0111(6) -0.0018(6) N2 0.0371(9) 0.0677(14) 0.0662(13) 0.0097(11) 0.0176(9) 0.0094(9) C1 0.0270(8) 0.0347(9) 0.0432(10) -0.0039(7) 0.0121(7) -0.0012(7) C2 0.0362(9) 0.0599(14) 0.0423(10) -0.0166(10) 0.0107(8) -0.0025(9) C3 0.0342(9) 0.0631(13) 0.0432(11) -0.0076(10) 0.0021(8) 0.0052(10) C4 0.0321(10) 0.0647(15) 0.0703(15) -0.0168(13) 0.0138(10) -0.0063(10) C5 0.0366(9) 0.0530(12) 0.0644(13) -0.0055(11) 0.0239(9) -0.0070(9) C6 0.0303(8) 0.0390(9) 0.0381(9) -0.0042(8) 0.0129(7) -0.0008(7) C7 0.0355(9) 0.0415(10) 0.0500(11) 0.0007(9) 0.0096(8) 0.0064(8) C8 0.0645(15) 0.0430(12) 0.0603(15) 0.0133(11) 0.0150(12) 0.0045(11) C9 0.0531(14) 0.0639(17) 0.085(2) -0.0078(15) 0.0213(13) 0.0232(13) C10 0.0402(9) 0.0664(13) 0.0392(9) -0.0073(11) 0.0165(7) -0.0041(11) C11 0.0323(9) 0.0416(10) 0.0487(11) -0.0006(8) 0.0155(8) 0.0022(8) C12 0.0301(8) 0.0459(10) 0.0568(12) -0.0002(10) 0.0170(8) 0.0000(8) C13 0.0321(10) 0.0498(12) 0.0902(19) 0.0094(13) 0.0160(11) 0.0043(9) C14 0.0495(15) 0.143(4) 0.084(2) -0.045(3) -0.0093(14) 0.023(2) C15 0.0422(10) 0.0638(15) 0.0466(11) 0.0013(11) 0.0024(9) 0.0010(11) C16 0.0588(14) 0.0740(19) 0.0620(16) 0.0032(14) 0.0070(12) -0.0164(14) C17 0.101(3) 0.079(2) 0.0681(19) -0.0197(18) 0.0021(18) -0.007(2) C18 0.120(3) 0.114(3) 0.0534(18) -0.012(2) 0.023(2) 0.030(3) C19 0.081(2) 0.126(4) 0.0699(19) 0.027(2) 0.0393(18) 0.017(2) C20 0.0541(14) 0.0664(17) 0.0758(18) 0.0082(14) 0.0155(13) -0.0062(13) C21 0.0416(10) 0.0595(14) 0.0661(13) 0.0007(12) 0.0301(10) 0.0007(11) C22 0.0494(11) 0.0545(13) 0.0485(11) -0.0018(10) 0.0285(9) -0.0062(10) C23 0.0717(17) 0.0654(18) 0.0565(14) -0.0094(12) 0.0225(13) -0.0113(13) C24 0.077(2) 0.107(3) 0.0474(13) 0.0096(17) 0.0106(13) -0.006(2) C25 0.085(2) 0.091(2) 0.0681(19) 0.0327(19) 0.0329(17) 0.018(2) C26 0.093(2) 0.0549(16) 0.090(2) 0.0080(16) 0.046(2) 0.0049(17) C27 0.0653(15) 0.0563(14) 0.0638(15) -0.0076(12) 0.0288(12) -0.0089(13) _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 S1 O1 1.4262(19) . ? S1 O2 1.4313(19) . ? S1 N1 1.6994(17) . ? S1 C10 1.782(2) . ? O3 C11 1.215(3) . ? O4 N2 1.391(4) . ? O4 C14 1.441(3) . ? N1 C11 1.385(2) . ? N1 C1 1.480(2) . ? N2 C13 1.267(4) . ? C1 C2 1.543(3) . ? C1 C6 1.546(2) . ? C2 C3 1.545(3) . ? C3 C4 1.533(4) . ? C3 C7 1.543(3) . ? C4 C5 1.550(4) . ? C5 C6 1.541(3) . ? C6 C10 1.512(3) . ? C6 C7 1.561(3) . ? C7 C9 1.535(3) . ? C7 C8 1.536(4) . ? C11 C12 1.529(3) . ? C12 C13 1.502(3) . ? C12 C21 1.556(3) . ? C14 C15 1.485(5) . ? C15 C16 1.374(4) . ? C15 C20 1.381(4) . ? C16 C17 1.352(5) . ? C17 C18 1.367(7) . ? C18 C19 1.396(7) . ? C19 C20 1.375(6) . ? C21 C22 1.504(4) . ? C22 C23 1.390(4) . ? C22 C27 1.394(4) . ? C23 C24 1.385(5) . ? C24 C25 1.382(7) . ? C25 C26 1.373(6) . ? C26 C27 1.365(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 117.75(12) . . ? O1 S1 N1 110.33(10) . . ? O2 S1 N1 108.23(11) . . ? O1 S1 C10 111.43(14) . . ? O2 S1 C10 111.13(13) . . ? N1 S1 C10 95.70(9) . . ? N2 O4 C14 110.0(3) . . ? C11 N1 C1 119.69(16) . . ? C11 N1 S1 121.65(14) . . ? C1 N1 S1 111.94(12) . . ? C13 N2 O4 110.2(2) . . ? N1 C1 C2 116.13(16) . . ? N1 C1 C6 106.01(15) . . ? C2 C1 C6 103.30(15) . . ? C1 C2 C3 102.16(16) . . ? C4 C3 C7 103.66(19) . . ? C4 C3 C2 108.0(2) . . ? C7 C3 C2 101.91(16) . . ? C3 C4 C5 103.40(18) . . ? C6 C5 C4 102.20(19) . . ? C10 C6 C5 116.46(18) . . ? C10 C6 C1 108.82(16) . . ? C5 C6 C1 105.27(17) . . ? C10 C6 C7 118.7(2) . . ? C5 C6 C7 102.29(17) . . ? C1 C6 C7 103.80(16) . . ? C9 C7 C8 106.7(2) . . ? C9 C7 C3 114.4(2) . . ? C8 C7 C3 114.4(2) . . ? C9 C7 C6 112.4(2) . . ? C8 C7 C6 116.80(18) . . ? C3 C7 C6 92.00(17) . . ? C6 C10 S1 107.15(13) . . ? O3 C11 N1 120.50(19) . . ? O3 C11 C12 122.16(18) . . ? N1 C11 C12 117.25(19) . . ? C13 C12 C11 110.0(2) . . ? C13 C12 C21 109.50(19) . . ? C11 C12 C21 108.84(19) . . ? N2 C13 C12 127.5(3) . . ? O4 C14 C15 110.3(2) . . ? C16 C15 C20 118.5(3) . . ? C16 C15 C14 120.9(3) . . ? C20 C15 C14 120.6(3) . . ? C17 C16 C15 121.5(3) . . ? C16 C17 C18 120.5(4) . . ? C17 C18 C19 119.5(4) . . ? C20 C19 C18 119.3(4) . . ? C19 C20 C15 120.7(3) . . ? C22 C21 C12 113.43(17) . . ? C23 C22 C27 117.9(3) . . ? C23 C22 C21 120.9(3) . . ? C27 C22 C21 121.2(3) . . ? C24 C23 C22 120.9(3) . . ? C25 C24 C23 120.1(3) . . ? C26 C25 C24 119.0(3) . . ? C27 C26 C25 121.3(3) . . ? C26 C27 C22 120.7(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.181 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.030 data_3aA _database_code_CSD 135459 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H38 N2 O4 S' _chemical_formula_weight 510.67 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting MONOCLINIC _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 12.2395(15) _cell_length_b 20.5642(14) _cell_length_c 10.9040(16) _cell_angle_alpha 90.00 _cell_angle_beta 94.209(11) _cell_angle_gamma 90.00 _cell_volume 2737.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 35 _cell_measurement_theta_max 45 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 1.339 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'nomal-focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5R diffractometer' _diffrn_measurement_method ot _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0.0 _diffrn_reflns_number 10002 _diffrn_reflns_av_R_equivalents 0.0627 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.62 _diffrn_reflns_theta_max 64.99 _reflns_number_total 6927 _reflns_number_gt 6029 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Rigaku/MSC AFC5R software 1992' _computing_cell_refinement 'Rigaku/MSC AFC5R software 1992' _computing_data_reduction 'Rigaku/MSC AFC5R software 1992' _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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00042(18) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.015(17) _refine_ls_number_reflns 6927 _refine_ls_number_parameters 650 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0507 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1305 _refine_ls_wR_factor_gt 0.1229 _refine_ls_goodness_of_fit_ref 0.970 _refine_ls_restrained_S_all 0.970 _refine_ls_shift/su_max 0.028 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.78614(7) -0.49437(4) 0.36740(7) 0.0454(2) Uani 1 1 d . . . S2 S 0.71830(7) -0.60221(4) 0.86544(8) 0.0499(2) Uani 1 1 d . . . O1 O 0.6993(2) -0.50512(13) 0.4429(2) 0.0619(7) Uani 1 1 d . . . O2 O 0.8821(2) -0.53210(13) 0.3923(3) 0.0633(7) Uani 1 1 d . . . O3 O 0.9173(2) -0.32966(13) 0.4435(3) 0.0661(7) Uani 1 1 d . . . O4 O 1.0046(3) -0.49109(17) 0.7799(3) 0.0793(9) Uani 1 1 d . . . O5 O 0.8038(3) -0.59138(15) 0.9592(3) 0.0754(8) Uani 1 1 d . . . O6 O 0.6216(3) -0.56511(13) 0.8716(3) 0.0745(8) Uani 1 1 d . . . O7 O 0.5904(2) -0.76871(12) 0.9136(2) 0.0589(7) Uani 1 1 d . . . O8 O 0.5139(2) -0.61234(16) 1.2481(3) 0.0772(9) Uani 1 1 d . . . N1 N 0.8188(2) -0.41395(13) 0.3692(2) 0.0437(6) Uani 1 1 d . . . N2 N 1.0541(3) -0.42989(17) 0.7527(3) 0.0635(9) Uani 1 1 d . . . N3 N 0.6871(2) -0.68319(13) 0.8585(2) 0.0426(6) Uani 1 1 d . . . N4 N 0.4577(3) -0.67064(16) 1.2088(3) 0.0591(8) Uani 1 1 d . . . C1 C 0.7384(3) -0.42863(17) 0.1589(3) 0.0459(8) Uani 1 1 d . . . C2 C 0.8143(3) -0.38579(18) 0.2436(3) 0.0456(8) Uani 1 1 d . . . C3 C 0.7637(3) -0.31739(16) 0.2270(3) 0.0509(8) Uani 1 1 d . . . C4 C 0.6785(3) -0.32771(18) 0.1193(3) 0.0534(9) Uani 1 1 d . . . C5 C 0.7387(4) -0.3460(2) 0.0057(4) 0.0657(11) Uani 1 1 d . . . C6 C 0.7744(3) -0.4171(2) 0.0295(3) 0.0590(9) Uani 1 1 d . . . C7 C 0.6266(3) -0.39258(17) 0.1533(3) 0.0495(8) Uani 1 1 d . . . C8 C 0.5687(3) -0.38910(19) 0.2729(4) 0.0584(9) Uani 1 1 d . . . C9 C 0.5428(4) -0.4191(2) 0.0535(4) 0.0690(11) Uani 1 1 d . . . C10 C 0.7426(3) -0.49798(19) 0.2070(3) 0.0508(8) Uani 1 1 d . . . C11 C 0.8798(3) -0.38273(17) 0.4631(3) 0.0448(7) Uani 1 1 d . . . C12 C 0.8970(3) -0.41350(18) 0.5894(3) 0.0504(8) Uani 1 1 d . . . C13 C 1.0228(3) -0.41378(19) 0.6239(4) 0.0571(9) Uani 1 1 d . . . C14 C 1.0873(4) -0.4558(2) 0.5408(4) 0.0681(11) Uani 1 1 d . . . C15 C 1.2089(4) -0.4449(3) 0.5573(5) 0.0885(15) Uani 1 1 d . . . C16 C 1.0874(4) -0.5297(2) 0.8450(4) 0.0799(14) Uani 1 1 d . . . C17 C 1.1190(3) -0.50283(19) 0.9721(4) 0.0590(9) Uani 1 1 d . . . C18 C 1.2083(4) -0.4631(2) 0.9930(4) 0.0691(11) Uani 1 1 d . . . C19 C 1.2352(4) -0.4377(2) 1.1078(5) 0.0756(12) Uani 1 1 d . . . C20 C 1.1743(5) -0.4520(3) 1.2027(4) 0.0828(14) Uani 1 1 d . . . C21 C 1.0851(4) -0.4937(3) 1.1846(5) 0.0894(15) Uani 1 1 d . . . C22 C 1.0579(3) -0.5178(2) 1.0692(5) 0.0739(12) Uani 1 1 d . . . C23 C 0.8364(4) -0.3730(2) 0.6809(4) 0.0693(11) Uani 1 1 d . . . C24 C 0.7155(3) -0.3666(2) 0.6541(3) 0.0585(10) Uani 1 1 d . . . C25 C 0.6698(4) -0.3120(2) 0.5973(5) 0.0775(13) Uani 1 1 d . . . C26 C 0.5554(6) -0.3062(3) 0.5748(5) 0.105(2) Uani 1 1 d . . . C27 C 0.4899(5) -0.3556(5) 0.6096(7) 0.113(2) Uani 1 1 d . . . C28 C 0.5334(5) -0.4089(3) 0.6634(7) 0.108(2) Uani 1 1 d . . . C29 C 0.6450(4) -0.4144(2) 0.6870(4) 0.0755(12) Uani 1 1 d . . . C30 C 0.7715(3) -0.66607(16) 0.6649(3) 0.0450(8) Uani 1 1 d . . . C31 C 0.6920(3) -0.70875(17) 0.7326(3) 0.0422(7) Uani 1 1 d . . . C32 C 0.7414(3) -0.77776(17) 0.7205(4) 0.0532(9) Uani 1 1 d . . . C33 C 0.8293(3) -0.76666(18) 0.6321(4) 0.0574(10) Uani 1 1 d . . . C34 C 0.7751(4) -0.7467(2) 0.5059(4) 0.0686(11) Uani 1 1 d . . . C35 C 0.7382(3) -0.6754(2) 0.5278(3) 0.0581(9) Uani 1 1 d . . . C36 C 0.8822(3) -0.70276(17) 0.6792(3) 0.0523(9) Uani 1 1 d . . . C37 C 0.9356(3) -0.7079(2) 0.8121(4) 0.0674(11) Uani 1 1 d . . . C38 C 0.9694(4) -0.6750(2) 0.5990(5) 0.0765(13) Uani 1 1 d . . . C39 C 0.7663(3) -0.59701(18) 0.7139(3) 0.0501(8) Uani 1 1 d . . . C40 C 0.6273(3) -0.71566(18) 0.9411(3) 0.0456(8) Uani 1 1 d . . . C41 C 0.6117(3) -0.68684(18) 1.0682(3) 0.0481(8) Uani 1 1 d . . . C42 C 0.4869(3) -0.68738(18) 1.0854(3) 0.0525(8) Uani 1 1 d . . . C43 C 0.4221(3) -0.6443(2) 0.9923(4) 0.0643(10) Uani 1 1 d . . . C44 C 0.2993(4) -0.6514(3) 0.9950(5) 0.0823(14) Uani 1 1 d . . . C45 C 0.4366(4) -0.5687(2) 1.2934(4) 0.0800(14) Uani 1 1 d . . . C46 C 0.3889(3) -0.5921(2) 1.4096(4) 0.0616(10) Uani 1 1 d . . . C47 C 0.4461(4) -0.5829(3) 1.5201(5) 0.0815(14) Uani 1 1 d . . . C48 C 0.4049(6) -0.6033(4) 1.6280(5) 0.110(2) Uani 1 1 d . . . C49 C 0.3049(9) -0.6350(4) 1.6205(8) 0.137(3) Uani 1 1 d . . . C50 C 0.2478(6) -0.6435(4) 1.5096(9) 0.142(3) Uani 1 1 d . . . C51 C 0.2889(4) -0.6210(3) 1.4051(5) 0.100(2) Uani 1 1 d . . . C52 C 0.6750(3) -0.7292(2) 1.1664(3) 0.0614(10) Uani 1 1 d . . . C53 C 0.7965(3) -0.73039(19) 1.1598(3) 0.0518(9) Uani 1 1 d . . . C54 C 0.8486(4) -0.7806(2) 1.1035(4) 0.0667(11) Uani 1 1 d . . . C55 C 0.9610(5) -0.7802(3) 1.0968(5) 0.0869(16) Uani 1 1 d . . . C56 C 1.0232(4) -0.7315(4) 1.1465(6) 0.0973(19) Uani 1 1 d . . . C57 C 0.9741(4) -0.6817(3) 1.2046(6) 0.0913(17) Uani 1 1 d . . . C58 C 0.8614(4) -0.6807(2) 1.2106(4) 0.0686(11) Uani 1 1 d . . . H1 H 0.8843 -0.3862 0.2148 0.053 Uiso 1 1 d . . . H2 H 0.8185 -0.2865 0.2077 0.062 Uiso 1 1 d . . . H3 H 0.7314 -0.3032 0.2991 0.062 Uiso 1 1 d . . . H4 H 0.6280 -0.2923 0.1066 0.064 Uiso 1 1 d . . . H5 H 0.6915 -0.3427 -0.0685 0.079 Uiso 1 1 d . . . H6 H 0.8012 -0.3189 -0.0035 0.079 Uiso 1 1 d . . . H7 H 0.7372 -0.4458 -0.0283 0.069 Uiso 1 1 d . . . H8 H 0.8509 -0.4221 0.0262 0.069 Uiso 1 1 d . . . H9 H 0.5068 -0.3609 0.2616 0.071 Uiso 1 1 d . . . H10 H 0.5453 -0.4310 0.2946 0.071 Uiso 1 1 d . . . H11 H 0.6180 -0.3721 0.3363 0.071 Uiso 1 1 d . . . H12 H 0.4811 -0.3900 0.0436 0.081 Uiso 1 1 d . . . H13 H 0.5174 -0.4606 0.0761 0.081 Uiso 1 1 d . . . H14 H 0.5750 -0.4220 -0.0231 0.081 Uiso 1 1 d . . . H15 H 0.6697 -0.5167 0.1977 0.059 Uiso 1 1 d . . . H16 H 0.7902 -0.5239 0.1646 0.059 Uiso 1 1 d . . . H17 H 0.8715 -0.4575 0.5877 0.057 Uiso 1 1 d . . . H18 H 1.0447 -0.3694 0.6148 0.066 Uiso 1 1 d . . . H19 H 1.0627 -0.4456 0.4578 0.085 Uiso 1 1 d . . . H20 H 1.0717 -0.4999 0.5568 0.085 Uiso 1 1 d . . . H21 H 1.2274 -0.4018 0.5310 0.112 Uiso 1 1 d . . . H22 H 1.2474 -0.4756 0.5128 0.112 Uiso 1 1 d . . . H23 H 1.2337 -0.4482 0.6434 0.112 Uiso 1 1 d . . . H24 H 1.0026 -0.4027 0.8217 0.090 Uiso 1 1 d . . . H25 H 1.1498 -0.5314 0.8008 0.098 Uiso 1 1 d . . . H26 H 1.0593 -0.5731 0.8551 0.098 Uiso 1 1 d . . . H27 H 1.2530 -0.4554 0.9282 0.083 Uiso 1 1 d . . . H28 H 1.2972 -0.4094 1.1201 0.093 Uiso 1 1 d . . . H29 H 1.1935 -0.4354 1.2819 0.104 Uiso 1 1 d . . . H30 H 1.0430 -0.5039 1.2498 0.107 Uiso 1 1 d . . . H31 H 0.9954 -0.5457 1.0547 0.087 Uiso 1 1 d . . . H32 H 0.8670 -0.3304 0.6852 0.077 Uiso 1 1 d . . . H33 H 0.8479 -0.3926 0.7614 0.077 Uiso 1 1 d . . . H34 H 0.7160 -0.2769 0.5731 0.094 Uiso 1 1 d . . . H35 H 0.5264 -0.2672 0.5358 0.115 Uiso 1 1 d . . . H36 H 0.4133 -0.3521 0.5868 0.131 Uiso 1 1 d . . . H37 H 0.4857 -0.4414 0.6860 0.124 Uiso 1 1 d . . . H38 H 0.6761 -0.4523 0.7280 0.089 Uiso 1 1 d . . . H39 H 0.6214 -0.7071 0.6902 0.050 Uiso 1 1 d . . . H40 H 0.7721 -0.7931 0.7983 0.061 Uiso 1 1 d . . . H41 H 0.6872 -0.8080 0.6892 0.061 Uiso 1 1 d . . . H42 H 0.8795 -0.8015 0.6268 0.067 Uiso 1 1 d . . . H43 H 0.7134 -0.7740 0.4833 0.082 Uiso 1 1 d . . . H44 H 0.8252 -0.7493 0.4434 0.082 Uiso 1 1 d . . . H45 H 0.6613 -0.6693 0.5109 0.069 Uiso 1 1 d . . . H46 H 0.7758 -0.6449 0.4789 0.069 Uiso 1 1 d . . . H47 H 0.9916 -0.7402 0.8126 0.077 Uiso 1 1 d . . . H48 H 0.8807 -0.7220 0.8640 0.077 Uiso 1 1 d . . . H49 H 0.9639 -0.6679 0.8369 0.077 Uiso 1 1 d . . . H50 H 1.0329 -0.7003 0.6064 0.091 Uiso 1 1 d . . . H51 H 0.9402 -0.6732 0.5159 0.091 Uiso 1 1 d . . . H52 H 0.9866 -0.6311 0.6258 0.091 Uiso 1 1 d . . . H53 H 0.8365 -0.5764 0.7179 0.060 Uiso 1 1 d . . . H54 H 0.7164 -0.5706 0.6628 0.060 Uiso 1 1 d . . . H55 H 0.6384 -0.6437 1.0744 0.055 Uiso 1 1 d . . . H56 H 0.4630 -0.7307 1.0707 0.063 Uiso 1 1 d . . . H57 H 0.4434 -0.6549 0.9131 0.078 Uiso 1 1 d . . . H58 H 0.4407 -0.6002 1.0110 0.078 Uiso 1 1 d . . . H59 H 0.2791 -0.6954 0.9711 0.100 Uiso 1 1 d . . . H60 H 0.2635 -0.6225 0.9379 0.100 Uiso 1 1 d . . . H61 H 0.2774 -0.6438 1.0747 0.100 Uiso 1 1 d . . . H62 H 0.4855 -0.7090 1.2648 0.090 Uiso 1 1 d . . . H63 H 0.4703 -0.5266 1.3099 0.096 Uiso 1 1 d . . . H64 H 0.3774 -0.5620 1.2319 0.096 Uiso 1 1 d . . . H65 H 0.5152 -0.5618 1.5253 0.095 Uiso 1 1 d . . . H66 H 0.4428 -0.6000 1.7031 0.137 Uiso 1 1 d . . . H67 H 0.2751 -0.6504 1.6952 0.169 Uiso 1 1 d . . . H68 H 0.1777 -0.6649 1.5043 0.167 Uiso 1 1 d . . . H69 H 0.2473 -0.6232 1.3283 0.123 Uiso 1 1 d . . . H70 H 0.6501 -0.7735 1.1537 0.069 Uiso 1 1 d . . . H71 H 0.6590 -0.7154 1.2448 0.069 Uiso 1 1 d . . . H72 H 0.8068 -0.8149 1.0665 0.083 Uiso 1 1 d . . . H73 H 0.9955 -0.8154 1.0564 0.105 Uiso 1 1 d . . . H74 H 1.1004 -0.7309 1.1415 0.114 Uiso 1 1 d . . . H75 H 1.0169 -0.6471 1.2447 0.107 Uiso 1 1 d . . . H76 H 0.8275 -0.6462 1.2515 0.078 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 S1 0.0524(4) 0.0380(4) 0.0456(4) 0.0028(3) 0.0028(3) -0.0043(4) S2 0.0623(5) 0.0390(4) 0.0498(5) -0.0036(4) 0.0142(4) -0.0053(4) O1 0.0720(16) 0.0585(16) 0.0565(15) 0.0017(12) 0.0125(12) -0.0196(13) O2 0.0717(17) 0.0467(14) 0.0698(17) 0.0008(12) -0.0055(13) 0.0039(13) O3 0.0711(17) 0.0531(16) 0.0713(17) 0.0076(13) -0.0136(13) -0.0201(13) O4 0.0820(19) 0.082(2) 0.0705(17) 0.0150(16) -0.0191(15) -0.0158(18) O5 0.096(2) 0.0707(19) 0.0591(16) -0.0031(14) 0.0010(15) -0.0323(17) O6 0.087(2) 0.0504(15) 0.090(2) 0.0025(14) 0.0322(17) 0.0077(14) O7 0.0685(16) 0.0493(14) 0.0616(16) -0.0076(12) 0.0234(13) -0.0159(12) O8 0.0750(18) 0.085(2) 0.0758(19) -0.0234(16) 0.0341(15) -0.0213(16) N1 0.0473(15) 0.0390(15) 0.0445(15) 0.0036(12) 0.0011(12) -0.0051(12) N2 0.070(2) 0.0576(19) 0.0608(19) 0.0023(15) -0.0131(16) -0.0053(16) N3 0.0458(15) 0.0431(15) 0.0398(14) -0.0013(12) 0.0096(11) -0.0027(12) N4 0.0634(19) 0.0611(19) 0.0552(18) -0.0054(15) 0.0211(15) -0.0095(16) C1 0.0527(19) 0.0445(19) 0.0409(17) -0.0005(14) 0.0068(14) 0.0024(15) C2 0.0426(17) 0.0512(19) 0.0438(18) 0.0087(15) 0.0098(14) -0.0021(15) C3 0.058(2) 0.0392(18) 0.055(2) 0.0071(15) 0.0024(16) -0.0047(15) C4 0.056(2) 0.051(2) 0.054(2) 0.0122(17) 0.0038(16) 0.0054(17) C5 0.078(3) 0.068(3) 0.051(2) 0.0128(19) 0.0077(19) 0.002(2) C6 0.062(2) 0.070(3) 0.0446(19) 0.0023(19) 0.0068(16) 0.0076(19) C7 0.0476(18) 0.0502(19) 0.0503(19) 0.0005(16) 0.0007(15) 0.0014(16) C8 0.051(2) 0.054(2) 0.072(2) 0.0002(18) 0.0128(18) -0.0031(17) C9 0.067(3) 0.070(3) 0.068(3) -0.006(2) -0.007(2) 0.000(2) C10 0.059(2) 0.0475(18) 0.0458(18) -0.0043(16) 0.0013(15) 0.0000(17) C11 0.0378(16) 0.0449(19) 0.0516(19) 0.0002(15) 0.0017(14) 0.0003(15) C12 0.055(2) 0.049(2) 0.0466(19) -0.0042(16) -0.0020(15) -0.0078(16) C13 0.055(2) 0.056(2) 0.058(2) 0.0027(18) -0.0071(17) -0.0058(17) C14 0.059(2) 0.083(3) 0.061(2) 0.004(2) -0.0027(19) 0.002(2) C15 0.059(3) 0.108(4) 0.097(4) 0.004(3) 0.000(2) 0.004(3) C16 0.109(4) 0.053(2) 0.074(3) 0.005(2) -0.020(3) -0.006(2) C17 0.059(2) 0.051(2) 0.065(2) 0.0070(19) -0.0073(18) 0.0042(18) C18 0.067(3) 0.077(3) 0.064(3) 0.004(2) 0.007(2) -0.006(2) C19 0.066(3) 0.079(3) 0.080(3) -0.004(2) -0.003(2) -0.010(2) C20 0.095(4) 0.092(3) 0.061(3) -0.006(2) 0.004(2) -0.004(3) C21 0.083(3) 0.114(4) 0.074(3) 0.001(3) 0.021(2) -0.009(3) C22 0.056(2) 0.078(3) 0.088(3) 0.010(2) 0.004(2) -0.010(2) C23 0.070(3) 0.084(3) 0.053(2) -0.015(2) -0.0052(19) -0.006(2) C24 0.066(2) 0.064(3) 0.045(2) -0.0158(18) 0.0054(17) 0.0053(19) C25 0.090(3) 0.068(3) 0.074(3) -0.005(2) 0.007(2) 0.016(3) C26 0.129(5) 0.098(4) 0.085(4) -0.011(3) -0.005(3) 0.059(4) C27 0.074(4) 0.134(6) 0.128(5) -0.034(5) -0.009(3) 0.022(4) C28 0.082(4) 0.097(4) 0.149(6) -0.040(4) 0.026(4) -0.012(3) C29 0.076(3) 0.067(3) 0.084(3) -0.015(2) 0.012(2) 0.003(2) C30 0.0530(19) 0.0419(19) 0.0413(17) 0.0051(14) 0.0117(14) -0.0003(15) C31 0.0384(16) 0.0475(18) 0.0413(17) -0.0072(14) 0.0065(13) -0.0005(14) C32 0.060(2) 0.0395(19) 0.062(2) -0.0037(16) 0.0174(17) -0.0060(16) C33 0.065(2) 0.0430(19) 0.068(2) -0.0025(17) 0.0305(19) 0.0098(17) C34 0.091(3) 0.062(2) 0.055(2) -0.0100(19) 0.024(2) -0.005(2) C35 0.073(2) 0.059(2) 0.043(2) 0.0010(17) 0.0110(17) 0.0010(19) C36 0.0497(19) 0.051(2) 0.058(2) 0.0066(17) 0.0154(16) 0.0031(16) C37 0.049(2) 0.073(3) 0.080(3) 0.010(2) 0.003(2) -0.001(2) C38 0.061(2) 0.074(3) 0.099(3) 0.008(3) 0.035(2) 0.000(2) C39 0.0582(19) 0.0430(18) 0.0496(19) 0.0047(15) 0.0072(15) -0.0042(16) C40 0.0417(17) 0.0472(19) 0.0482(18) -0.0007(15) 0.0057(14) 0.0032(15) C41 0.0505(19) 0.052(2) 0.0426(18) -0.0009(15) 0.0114(15) -0.0045(16) C42 0.058(2) 0.0502(19) 0.052(2) -0.0006(16) 0.0175(16) -0.0002(16) C43 0.056(2) 0.075(3) 0.063(2) 0.000(2) 0.0141(19) 0.009(2) C44 0.069(3) 0.093(3) 0.085(3) -0.008(3) 0.009(2) 0.024(3) C45 0.106(4) 0.062(3) 0.077(3) -0.010(2) 0.040(3) -0.009(3) C46 0.058(2) 0.056(2) 0.074(3) -0.0115(19) 0.026(2) -0.0006(18) C47 0.061(3) 0.103(4) 0.081(3) -0.008(3) 0.011(2) 0.004(3) C48 0.126(5) 0.132(5) 0.075(3) 0.013(4) 0.020(3) 0.027(5) C49 0.196(8) 0.120(6) 0.109(5) 0.000(4) 0.101(6) -0.010(6) C50 0.128(6) 0.151(7) 0.160(7) -0.052(6) 0.094(6) -0.061(5) C51 0.074(3) 0.138(5) 0.092(4) -0.046(4) 0.036(3) -0.032(3) C52 0.070(2) 0.071(3) 0.045(2) 0.0098(18) 0.0109(17) 0.008(2) C53 0.058(2) 0.055(2) 0.0431(18) 0.0137(16) 0.0043(16) 0.0067(17) C54 0.083(3) 0.059(2) 0.057(2) 0.0127(19) 0.002(2) 0.012(2) C55 0.081(4) 0.094(4) 0.088(3) 0.030(3) 0.022(3) 0.038(3) C56 0.058(3) 0.127(5) 0.107(4) 0.057(4) 0.007(3) 0.017(3) C57 0.071(3) 0.094(4) 0.105(4) 0.033(3) -0.023(3) -0.027(3) C58 0.082(3) 0.063(2) 0.059(2) 0.011(2) -0.002(2) 0.002(2) _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 S1 O1 1.409(3) . ? S1 O2 1.417(3) . ? S1 N1 1.701(3) . ? S1 C10 1.792(3) . ? S2 O6 1.414(3) . ? S2 O5 1.426(3) . ? S2 N3 1.709(3) . ? S2 C39 1.797(4) . ? O3 C11 1.209(4) . ? O4 C16 1.434(6) . ? O4 N2 1.437(5) . ? O7 C40 1.210(4) . ? O8 C45 1.420(6) . ? O8 N4 1.433(4) . ? N1 C11 1.381(4) . ? N1 C2 1.485(4) . ? N2 C13 1.467(5) . ? N3 C40 1.374(4) . ? N3 C31 1.476(4) . ? N4 C42 1.458(5) . ? C1 C10 1.519(5) . ? C1 C6 1.528(5) . ? C1 C2 1.538(5) . ? C1 C7 1.553(5) . ? C2 C3 1.542(5) . ? C3 C4 1.526(5) . ? C4 C5 1.534(6) . ? C4 C7 1.534(5) . ? C5 C6 1.543(6) . ? C7 C8 1.531(5) . ? C7 C9 1.539(5) . ? C11 C12 1.516(5) . ? C12 C23 1.532(6) . ? C12 C13 1.558(5) . ? C13 C14 1.516(6) . ? C14 C15 1.503(7) . ? C16 C17 1.515(6) . ? C17 C18 1.371(6) . ? C17 C22 1.375(6) . ? C18 C19 1.373(7) . ? C19 C20 1.351(7) . ? C20 C21 1.390(8) . ? C21 C22 1.372(7) . ? C23 C24 1.492(6) . ? C24 C29 1.374(7) . ? C24 C25 1.381(6) . ? C25 C26 1.408(9) . ? C26 C27 1.365(10) . ? C27 C28 1.336(10) . ? C28 C29 1.376(8) . ? C30 C39 1.521(5) . ? C30 C35 1.532(5) . ? C30 C31 1.539(5) . ? C30 C36 1.548(5) . ? C31 C32 1.552(5) . ? C32 C33 1.514(5) . ? C33 C36 1.536(5) . ? C33 C34 1.539(6) . ? C34 C35 1.557(6) . ? C36 C38 1.539(6) . ? C36 C37 1.549(6) . ? C40 C41 1.532(5) . ? C41 C52 1.544(5) . ? C41 C42 1.554(5) . ? C42 C43 1.525(6) . ? C43 C44 1.512(7) . ? C45 C46 1.512(6) . ? C46 C51 1.358(6) . ? C46 C47 1.361(6) . ? C47 C48 1.379(8) . ? C48 C49 1.384(11) . ? C49 C50 1.363(12) . ? C50 C51 1.360(10) . ? C52 C53 1.494(6) . ? C53 C54 1.380(6) . ? C53 C58 1.385(6) . ? C54 C55 1.384(7) . ? C55 C56 1.348(9) . ? C56 C57 1.365(9) . ? C57 C58 1.386(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 116.88(17) . . ? O1 S1 N1 109.41(15) . . ? O2 S1 N1 109.85(15) . . ? O1 S1 C10 112.36(16) . . ? O2 S1 C10 110.33(17) . . ? N1 S1 C10 96.00(16) . . ? O6 S2 O5 117.1(2) . . ? O6 S2 N3 110.04(16) . . ? O5 S2 N3 109.48(16) . . ? O6 S2 C39 110.05(18) . . ? O5 S2 C39 112.19(17) . . ? N3 S2 C39 96.01(15) . . ? C16 O4 N2 107.0(3) . . ? C45 O8 N4 108.4(3) . . ? C11 N1 C2 119.0(3) . . ? C11 N1 S1 125.1(2) . . ? C2 N1 S1 112.1(2) . . ? O4 N2 C13 108.1(3) . . ? C40 N3 C31 119.7(3) . . ? C40 N3 S2 124.9(2) . . ? C31 N3 S2 111.3(2) . . ? O8 N4 C42 109.2(3) . . ? C10 C1 C6 117.3(3) . . ? C10 C1 C2 109.1(3) . . ? C6 C1 C2 105.2(3) . . ? C10 C1 C7 118.0(3) . . ? C6 C1 C7 101.7(3) . . ? C2 C1 C7 104.0(3) . . ? N1 C2 C1 108.1(3) . . ? N1 C2 C3 116.8(3) . . ? C1 C2 C3 103.4(3) . . ? C4 C3 C2 102.1(3) . . ? C3 C4 C5 108.3(3) . . ? C3 C4 C7 101.9(3) . . ? C5 C4 C7 102.3(3) . . ? C4 C5 C6 104.1(3) . . ? C1 C6 C5 101.8(3) . . ? C8 C7 C4 113.0(3) . . ? C8 C7 C9 107.0(3) . . ? C4 C7 C9 113.8(3) . . ? C8 C7 C1 116.8(3) . . ? C4 C7 C1 92.6(3) . . ? C9 C7 C1 113.5(3) . . ? C1 C10 S1 107.3(2) . . ? O3 C11 N1 118.7(3) . . ? O3 C11 C12 120.5(3) . . ? N1 C11 C12 120.7(3) . . ? C11 C12 C23 108.9(3) . . ? C11 C12 C13 106.8(3) . . ? C23 C12 C13 111.2(3) . . ? N2 C13 C14 109.4(3) . . ? N2 C13 C12 114.6(3) . . ? C14 C13 C12 114.0(3) . . ? C15 C14 C13 113.5(4) . . ? O4 C16 C17 112.0(4) . . ? C18 C17 C22 118.5(4) . . ? C18 C17 C16 121.1(4) . . ? C22 C17 C16 120.4(4) . . ? C17 C18 C19 120.9(4) . . ? C20 C19 C18 120.4(4) . . ? C19 C20 C21 119.8(5) . . ? C22 C21 C20 119.2(4) . . ? C21 C22 C17 121.1(4) . . ? C24 C23 C12 116.2(3) . . ? C29 C24 C25 117.3(4) . . ? C29 C24 C23 121.2(4) . . ? C25 C24 C23 121.6(4) . . ? C24 C25 C26 120.7(5) . . ? C27 C26 C25 119.1(5) . . ? C28 C27 C26 120.6(6) . . ? C27 C28 C29 120.5(6) . . ? C24 C29 C28 121.8(5) . . ? C39 C30 C35 116.4(3) . . ? C39 C30 C31 108.6(3) . . ? C35 C30 C31 105.3(3) . . ? C39 C30 C36 118.6(3) . . ? C35 C30 C36 101.9(3) . . ? C31 C30 C36 104.7(3) . . ? N3 C31 C30 108.3(3) . . ? N3 C31 C32 116.5(3) . . ? C30 C31 C32 102.5(3) . . ? C33 C32 C31 102.5(3) . . ? C32 C33 C36 102.6(3) . . ? C32 C33 C34 109.3(3) . . ? C36 C33 C34 102.3(3) . . ? C33 C34 C35 103.0(3) . . ? C30 C35 C34 102.0(3) . . ? C33 C36 C38 114.9(3) . . ? C33 C36 C30 92.3(3) . . ? C38 C36 C30 113.6(3) . . ? C33 C36 C37 113.1(3) . . ? C38 C36 C37 107.1(3) . . ? C30 C36 C37 115.7(3) . . ? C30 C39 S2 107.0(2) . . ? O7 C40 N3 118.9(3) . . ? O7 C40 C41 120.3(3) . . ? N3 C40 C41 120.8(3) . . ? C40 C41 C52 108.7(3) . . ? C40 C41 C42 107.2(3) . . ? C52 C41 C42 111.1(3) . . ? N4 C42 C43 109.1(3) . . ? N4 C42 C41 114.8(3) . . ? C43 C42 C41 112.5(3) . . ? C44 C43 C42 113.6(4) . . ? O8 C45 C46 113.5(4) . . ? C51 C46 C47 119.8(4) . . ? C51 C46 C45 120.7(4) . . ? C47 C46 C45 119.5(4) . . ? C46 C47 C48 121.1(5) . . ? C47 C48 C49 118.0(6) . . ? C50 C49 C48 120.4(6) . . ? C51 C50 C49 120.2(6) . . ? C46 C51 C50 120.4(6) . . ? C53 C52 C41 115.2(3) . . ? C54 C53 C58 117.4(4) . . ? C54 C53 C52 121.8(4) . . ? C58 C53 C52 120.8(4) . . ? C53 C54 C55 120.8(5) . . ? C56 C55 C54 121.1(5) . . ? C55 C56 C57 119.3(5) . . ? C56 C57 C58 120.5(5) . . ? C53 C58 C57 120.9(5) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 64.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.199 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.042