# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name _publ_author_address 'Marie-Christine Scherrmann' ;UMR 8182 Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay Universit\'e Paris-Sud B\^at 410-420 91405 Orsay Cedex FRANCE ; 'Nicolas Bragnier' ;UMR 8182 Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay Universit\'e Paris-Sud B\^at 410-420 91405 Orsay Cedex FRANCE ; 'Regis Guillot' ;UMR 8182 Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay Universit\'e Paris-Sud B\^at 410-420 91405 Orsay Cedex FRANCE ; _publ_contact_author_name 'Marie-Christine Scherrmann' _publ_contact_author_email MCSCHERR@ICMO.U-PSUD.FR _publ_section_title ; Diastereoselective addition of sugar radicals to camphorsultam glyoxilic oxime ether: A route toward C-glycosylthreonine and allothreonine ; _publ_contact_author_address ;UMR 8182 Institut de Chimie Mol\'eculaire et des Mat\'eriaux d'Orsay Universit\'e Paris-Sud B\^at 410-420 91405 Orsay Cedex FRANCE ; _publ_contact_author_fax '+33 (0)169154679' _publ_contact_author_phone '+ 33 (0)169157256' # Attachment 'RX265_17a_.cif' data_265GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 731615' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C36 H50 N2 O13 S' _chemical_formula_sum 'C36 H50 N2 O13 S' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour none _diffrn_ambient_temperature 100(1) _chemical_formula_weight 750.85 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 'P 21' _symmetry_int_tables_number 4 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.9756(5) _cell_length_b 17.3489(10) _cell_length_c 12.2509(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.036(2) _cell_angle_gamma 90.00 _cell_volume 1902.94(19) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 5446 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 30.47 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.080 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.310 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.977 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'X8 Apex II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10784 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0362 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 30.81 _reflns_number_total 7481 _reflns_number_gt 6895 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0502P)^2^+0.3016P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.04(5) _refine_ls_number_reflns 7481 _refine_ls_number_parameters 476 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0339 _refine_ls_wR_factor_ref 0.0882 _refine_ls_wR_factor_gt 0.0857 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0.015 _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 C18 C 0.6545(2) 0.11866(18) 0.24932(16) 0.0364(6) Uani 1 1 d . . . H18 H 0.6762 0.1399 0.3183 0.044 Uiso 1 1 calc R . . C19 C 0.6792(2) 0.04143(17) 0.23223(18) 0.0366(6) Uani 1 1 d . . . H19 H 0.7191 0.0107 0.2892 0.044 Uiso 1 1 calc R . . C20 C 0.6442(3) 0.00942(16) 0.12960(18) 0.0334(5) Uani 1 1 d . . . H20 H 0.6595 -0.0429 0.1180 0.040 Uiso 1 1 calc R . . C1 C 0.0876(2) -0.15075(12) -0.22228(15) 0.0198(4) Uani 1 1 d . . . H1A H 0.1502 -0.1715 -0.2766 0.024 Uiso 1 1 calc R . . H1B H 0.0552 -0.1929 -0.1777 0.024 Uiso 1 1 calc R . . C2 C -0.0472(2) -0.10949(11) -0.27803(14) 0.0161(4) Uani 1 1 d . . . C3 C -0.0939(2) -0.13102(12) -0.39741(15) 0.0200(4) Uani 1 1 d . . . H3A H -0.1031 -0.1864 -0.4064 0.024 Uiso 1 1 calc R . . H3B H -0.0231 -0.1115 -0.4469 0.024 Uiso 1 1 calc R . . C4 C -0.2483(2) -0.09040(12) -0.41663(15) 0.0209(4) Uani 1 1 d . . . H4A H -0.2457 -0.0511 -0.4729 0.025 Uiso 1 1 calc R . . H4B H -0.3263 -0.1273 -0.4377 0.025 Uiso 1 1 calc R . . C5 C -0.2730(2) -0.05420(11) -0.30429(15) 0.0174(4) Uani 1 1 d . . . H5A H -0.3777 -0.0431 -0.2925 0.021 Uiso 1 1 calc R . . C6 C -0.1988(2) -0.11298(11) -0.22331(15) 0.0176(4) Uani 1 1 d . . . C7 C -0.1975(2) -0.08827(13) -0.10285(14) 0.0222(4) Uani 1 1 d . . . H7A H -0.1343 -0.1224 -0.0587 0.033 Uiso 1 1 calc R . . H7B H -0.2972 -0.0904 -0.0793 0.033 Uiso 1 1 calc R . . H7C H -0.1601 -0.0366 -0.0952 0.033 Uiso 1 1 calc R . . C8 C -0.2737(2) -0.19270(13) -0.22906(19) 0.0272(4) Uani 1 1 d . . . H8A H -0.2248 -0.2260 -0.1752 0.041 Uiso 1 1 calc R . . H8B H -0.2658 -0.2143 -0.3006 0.041 Uiso 1 1 calc R . . H8C H -0.3771 -0.1876 -0.2150 0.041 Uiso 1 1 calc R . . C9 C -0.16849(19) 0.01594(11) -0.28940(14) 0.0164(3) Uani 1 1 d . . . H9A H -0.1860 0.0441 -0.2231 0.020 Uiso 1 1 calc R . . H9B H -0.1805 0.0506 -0.3515 0.020 Uiso 1 1 calc R . . C10 C -0.0119(2) -0.02230(11) -0.28165(14) 0.0149(3) Uani 1 1 d . . . H10A H 0.0420 -0.0098 -0.3462 0.018 Uiso 1 1 calc R . . C11 C 0.12002(19) 0.07143(11) -0.15596(13) 0.0149(3) Uani 1 1 d . . . C12 C 0.18507(19) 0.08841(11) -0.03966(13) 0.0149(3) Uani 1 1 d . . . H12A H 0.2543 0.0471 -0.0157 0.018 Uiso 1 1 calc R . . C13 C 0.05320(19) 0.09023(12) 0.03567(13) 0.0165(4) Uani 1 1 d . . . H13 H 0.0021 0.0403 0.0295 0.020 Uiso 1 1 calc R . . C14 C -0.0608(2) 0.15324(14) 0.00140(15) 0.0227(4) Uani 1 1 d . . . H14A H -0.1393 0.1533 0.0507 0.034 Uiso 1 1 calc R . . H14B H -0.1022 0.1433 -0.0716 0.034 Uiso 1 1 calc R . . H14C H -0.0121 0.2025 0.0037 0.034 Uiso 1 1 calc R . . C15 C 0.5158(2) 0.18468(13) -0.03604(16) 0.0236(4) Uani 1 1 d . . . H15A H 0.4923 0.2355 -0.0089 0.028 Uiso 1 1 calc R . . H15B H 0.5981 0.1902 -0.0827 0.028 Uiso 1 1 calc R . . C16 C 0.5646(2) 0.13389(13) 0.05950(15) 0.0222(4) Uani 1 1 d . . . C17 C 0.5971(2) 0.16510(15) 0.16356(16) 0.0289(5) Uani 1 1 d . . . H17 H 0.5803 0.2172 0.1757 0.035 Uiso 1 1 calc R . . C21 C 0.5864(2) 0.05591(14) 0.04440(17) 0.0260(4) Uani 1 1 d . . . H21 H 0.5620 0.0341 -0.0239 0.031 Uiso 1 1 calc R . . C22 C 0.1043(2) 0.10293(11) 0.15651(13) 0.0167(4) Uani 1 1 d . . . H22A H 0.1565 0.1519 0.1626 0.020 Uiso 1 1 calc R . . H22B H 0.0161 0.1074 0.1974 0.020 Uiso 1 1 calc R . . C23 C 0.2046(2) 0.04180(11) 0.21086(14) 0.0151(3) Uani 1 1 d . . . H23 H 0.2946 0.0368 0.1705 0.018 Uiso 1 1 calc R . . C24 C 0.25012(19) 0.06284(11) 0.32939(13) 0.0140(3) Uani 1 1 d . . . H24 H 0.3124 0.1093 0.3318 0.017 Uiso 1 1 calc R . . C25 C 0.3348(2) -0.00340(11) 0.38844(13) 0.0146(3) Uani 1 1 d . . . H25 H 0.4365 -0.0058 0.3642 0.018 Uiso 1 1 calc R . . C26 C 0.25862(18) -0.08026(12) 0.36757(13) 0.0148(3) Uani 1 1 d . . . H26 H 0.1691 -0.0840 0.4087 0.018 Uiso 1 1 calc R . . C27 C 0.2184(2) -0.09169(11) 0.24493(13) 0.0170(4) Uani 1 1 d . . . H27 H 0.3106 -0.0906 0.2066 0.020 Uiso 1 1 calc R . . C28 C 0.1386(2) -0.16642(12) 0.21848(15) 0.0210(4) Uani 1 1 d . . . H28A H 0.1051 -0.1675 0.1415 0.025 Uiso 1 1 calc R . . H28B H 0.2065 -0.2093 0.2331 0.025 Uiso 1 1 calc R . . C29 C -0.1235(2) -0.18546(12) 0.23068(15) 0.0225(4) Uani 1 1 d . . . C30 C -0.2424(3) -0.19283(15) 0.30840(17) 0.0322(5) Uani 1 1 d . . . H30A H -0.2625 -0.1432 0.3387 0.048 Uiso 1 1 calc R . . H30B H -0.2100 -0.2276 0.3663 0.048 Uiso 1 1 calc R . . H30C H -0.3317 -0.2125 0.2705 0.048 Uiso 1 1 calc R . . C31 C 0.3399(2) -0.18147(11) 0.49157(15) 0.0170(4) Uani 1 1 d . . . C32 C 0.4502(2) -0.24545(12) 0.50824(18) 0.0246(4) Uani 1 1 d . . . H32A H 0.4794 -0.2504 0.5848 0.037 Uiso 1 1 calc R . . H32B H 0.5365 -0.2344 0.4689 0.037 Uiso 1 1 calc R . . H32C H 0.4056 -0.2928 0.4817 0.037 Uiso 1 1 calc R . . C33 C 0.4577(2) 0.05453(11) 0.54719(14) 0.0158(4) Uani 1 1 d . . . C34 C 0.4313(2) 0.07980(12) 0.66112(14) 0.0196(4) Uani 1 1 d . . . H34A H 0.3541 0.1182 0.6585 0.029 Uiso 1 1 calc R . . H34B H 0.5218 0.1011 0.6952 0.029 Uiso 1 1 calc R . . H34C H 0.4012 0.0363 0.7027 0.029 Uiso 1 1 calc R . . C35 C 0.1153(2) 0.13931(10) 0.45063(13) 0.0148(3) Uani 1 1 d . . . C36 C -0.0320(2) 0.14975(12) 0.49886(15) 0.0208(4) Uani 1 1 d . . . H36A H -0.0177 0.1490 0.5772 0.031 Uiso 1 1 calc R . . H36B H -0.0981 0.1087 0.4748 0.031 Uiso 1 1 calc R . . H36C H -0.0747 0.1983 0.4755 0.031 Uiso 1 1 calc R . . N1 N 0.08126(17) -0.00510(9) -0.17996(12) 0.0156(3) Uani 1 1 d . . . N2 N 0.26313(16) 0.16172(10) -0.03284(12) 0.0159(3) Uani 1 1 d . . . H2 H 0.2388 0.2014 0.0041 0.019 Uiso 1 1 calc R . . O1 O 0.17755(16) -0.09437(9) -0.02418(10) 0.0253(3) Uani 1 1 d . . . O2 O 0.33644(15) -0.07119(10) -0.17476(12) 0.0278(3) Uani 1 1 d . . . O3 O 0.08656(15) 0.12188(8) -0.22154(10) 0.0189(3) Uani 1 1 d . . . O4 O 0.38932(13) 0.15568(9) -0.09960(10) 0.0202(3) Uani 1 1 d . . . O5 O 0.01154(16) -0.17402(9) 0.28416(10) 0.0226(3) Uani 1 1 d . . . O6 O 0.36368(15) -0.14028(8) 0.40082(10) 0.0171(3) Uani 1 1 d . . . O7 O 0.34151(14) 0.01098(8) 0.50476(9) 0.0161(3) Uani 1 1 d . . . O8 O 0.11438(13) 0.07726(8) 0.38383(9) 0.0150(3) Uani 1 1 d . . . O9 O -0.14295(18) -0.18945(10) 0.13248(11) 0.0300(3) Uani 1 1 d . . . O10 O 0.22172(15) 0.18085(8) 0.46851(11) 0.0206(3) Uani 1 1 d . . . O11 O 0.56435(14) 0.06993(8) 0.49723(10) 0.0192(3) Uani 1 1 d . . . O12 O 0.23964(17) -0.16916(10) 0.54867(12) 0.0302(4) Uani 1 1 d . . . O13 O 0.12548(14) -0.02979(8) 0.20582(10) 0.0169(3) Uani 1 1 d . . . S S 0.18929(5) -0.08121(3) -0.13858(3) 0.01725(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C18 0.0246(10) 0.0671(18) 0.0175(8) -0.0062(11) 0.0011(8) 0.0107(11) C19 0.0266(11) 0.0616(18) 0.0218(10) 0.0063(11) 0.0024(8) 0.0173(11) C20 0.0290(11) 0.0404(14) 0.0311(11) 0.0033(10) 0.0045(9) 0.0093(10) C1 0.0246(9) 0.0165(10) 0.0186(8) -0.0018(7) 0.0026(7) 0.0064(7) C2 0.0187(8) 0.0154(9) 0.0143(7) -0.0009(6) 0.0024(6) 0.0019(7) C3 0.0215(9) 0.0215(10) 0.0169(8) -0.0040(7) 0.0017(7) 0.0028(8) C4 0.0207(8) 0.0211(10) 0.0205(8) -0.0041(8) -0.0023(7) -0.0001(8) C5 0.0157(8) 0.0153(9) 0.0213(8) -0.0007(7) 0.0012(7) 0.0016(7) C6 0.0190(8) 0.0148(9) 0.0195(8) 0.0010(7) 0.0049(7) 0.0013(7) C7 0.0250(9) 0.0230(10) 0.0194(8) 0.0036(8) 0.0066(7) 0.0011(8) C8 0.0300(11) 0.0165(10) 0.0358(11) 0.0014(9) 0.0076(9) -0.0033(8) C9 0.0170(8) 0.0155(9) 0.0164(8) 0.0013(7) -0.0008(6) 0.0010(7) C10 0.0165(8) 0.0168(9) 0.0113(7) 0.0017(6) -0.0010(6) 0.0010(7) C11 0.0126(7) 0.0193(9) 0.0128(7) -0.0002(7) 0.0015(6) -0.0008(7) C12 0.0146(8) 0.0186(9) 0.0113(7) -0.0001(7) -0.0009(6) 0.0006(7) C13 0.0158(8) 0.0217(10) 0.0121(7) -0.0003(7) 0.0011(6) -0.0021(7) C14 0.0153(8) 0.0351(12) 0.0176(8) 0.0021(8) 0.0016(6) 0.0037(8) C15 0.0149(8) 0.0297(11) 0.0262(9) 0.0023(8) 0.0020(7) -0.0054(8) C16 0.0104(8) 0.0344(12) 0.0219(8) -0.0002(8) 0.0026(7) -0.0010(8) C17 0.0179(9) 0.0438(14) 0.0255(10) -0.0075(10) 0.0054(7) 0.0061(9) C21 0.0222(9) 0.0335(12) 0.0223(9) 0.0003(8) 0.0013(7) 0.0014(9) C22 0.0216(9) 0.0163(9) 0.0123(7) 0.0004(6) 0.0013(6) 0.0000(7) C23 0.0177(8) 0.0149(9) 0.0128(7) -0.0012(6) 0.0024(6) -0.0036(7) C24 0.0152(8) 0.0147(9) 0.0122(7) -0.0004(6) 0.0029(6) -0.0020(7) C25 0.0170(8) 0.0173(9) 0.0098(7) 0.0011(6) 0.0025(6) -0.0015(7) C26 0.0167(7) 0.0142(8) 0.0136(7) 0.0012(7) 0.0029(6) 0.0009(7) C27 0.0221(8) 0.0166(9) 0.0125(7) -0.0005(7) 0.0032(6) -0.0024(7) C28 0.0304(10) 0.0167(10) 0.0161(8) -0.0026(7) 0.0028(7) -0.0038(8) C29 0.0334(10) 0.0140(9) 0.0198(8) 0.0015(7) -0.0014(8) -0.0079(8) C30 0.0336(11) 0.0404(14) 0.0225(9) 0.0062(9) 0.0012(8) -0.0116(10) C31 0.0170(8) 0.0158(9) 0.0181(8) 0.0007(7) 0.0002(7) -0.0023(7) C32 0.0222(10) 0.0183(10) 0.0333(11) 0.0063(8) 0.0026(8) 0.0014(8) C33 0.0191(8) 0.0135(9) 0.0144(7) 0.0020(6) -0.0030(6) 0.0037(7) C34 0.0245(9) 0.0207(10) 0.0133(7) -0.0019(7) -0.0008(7) 0.0034(8) C35 0.0198(8) 0.0132(9) 0.0113(7) 0.0038(6) -0.0011(6) 0.0036(7) C36 0.0220(9) 0.0212(10) 0.0201(8) 0.0014(8) 0.0063(7) 0.0026(8) N1 0.0168(7) 0.0172(8) 0.0125(6) 0.0013(6) -0.0014(5) 0.0031(6) N2 0.0129(7) 0.0197(8) 0.0157(6) -0.0041(6) 0.0044(5) 0.0002(6) O1 0.0362(8) 0.0245(8) 0.0149(6) 0.0044(5) -0.0014(5) 0.0057(6) O2 0.0188(6) 0.0311(9) 0.0338(7) 0.0041(7) 0.0036(6) 0.0048(6) O3 0.0210(6) 0.0207(7) 0.0146(5) 0.0034(5) -0.0016(5) -0.0016(5) O4 0.0143(6) 0.0307(8) 0.0161(6) 0.0000(6) 0.0041(5) -0.0029(6) O5 0.0296(7) 0.0237(8) 0.0144(6) 0.0006(5) 0.0012(5) -0.0108(6) O6 0.0187(6) 0.0158(7) 0.0173(6) 0.0014(5) 0.0051(5) 0.0035(5) O7 0.0197(6) 0.0180(7) 0.0109(5) -0.0002(5) 0.0021(5) -0.0015(5) O8 0.0157(6) 0.0165(7) 0.0130(5) -0.0018(5) 0.0030(4) -0.0011(5) O9 0.0409(9) 0.0309(9) 0.0173(6) 0.0025(6) -0.0044(6) -0.0105(7) O10 0.0209(6) 0.0175(7) 0.0234(6) -0.0038(5) 0.0023(5) -0.0014(5) O11 0.0185(6) 0.0199(7) 0.0189(6) -0.0003(5) 0.0003(5) -0.0015(5) O12 0.0306(8) 0.0356(9) 0.0262(7) 0.0119(7) 0.0137(6) 0.0113(7) O13 0.0206(6) 0.0143(6) 0.0154(6) 0.0001(5) -0.0002(5) -0.0040(5) S 0.01817(19) 0.0194(2) 0.01407(18) 0.00247(18) 0.00024(15) 0.00511(18) _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 C18 C19 1.376(4) . ? C18 C17 1.394(3) . ? C18 H18 0.9300 . ? C19 C20 1.390(3) . ? C19 H19 0.9300 . ? C20 C21 1.390(3) . ? C20 H20 0.9300 . ? C1 C2 1.525(3) . ? C1 S 1.791(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.539(2) . ? C2 C10 1.547(3) . ? C2 C6 1.560(3) . ? C3 C4 1.557(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.543(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C9 1.539(3) . ? C5 C6 1.541(3) . ? C5 H5A 0.9800 . ? C6 C7 1.536(3) . ? C6 C8 1.537(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.551(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N1 1.481(2) . ? C10 H10A 0.9800 . ? C11 O3 1.211(2) . ? C11 N1 1.398(2) . ? C11 C12 1.530(2) . ? C12 N2 1.452(2) . ? C12 C13 1.551(2) . ? C12 H12A 0.9800 . ? C13 C22 1.535(2) . ? C13 C14 1.536(3) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O4 1.422(2) . ? C15 C16 1.505(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C21 1.381(3) . ? C16 C17 1.397(3) . ? C17 H17 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.515(2) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 O13 1.430(2) . ? C23 C24 1.525(2) . ? C23 H23 0.9800 . ? C24 O8 1.451(2) . ? C24 C25 1.531(2) . ? C24 H24 0.9800 . ? C25 O7 1.4437(19) . ? C25 C26 1.512(3) . ? C25 H25 0.9800 . ? C26 O6 1.444(2) . ? C26 C27 1.533(2) . ? C26 H26 0.9800 . ? C27 O13 1.422(2) . ? C27 C28 1.506(3) . ? C27 H27 0.9800 . ? C28 O5 1.447(2) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 O9 1.205(2) . ? C29 O5 1.352(2) . ? C29 C30 1.485(3) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 O12 1.198(2) . ? C31 O6 1.351(2) . ? C31 C32 1.491(3) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 O11 1.202(2) . ? C33 O7 1.361(2) . ? C33 C34 1.498(2) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 O10 1.204(2) . ? C35 O8 1.352(2) . ? C35 C36 1.497(2) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? N1 S 1.6946(16) . ? N2 O4 1.4468(18) . ? N2 H2 0.8600 . ? O1 S 1.4312(13) . ? O2 S 1.4331(14) . ? 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 C19 C18 C17 120.2(2) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C18 C19 C20 119.9(2) . . ? C18 C19 H19 120.1 . . ? C20 C19 H19 120.1 . . ? C19 C20 C21 119.7(2) . . ? C19 C20 H20 120.1 . . ? C21 C20 H20 120.1 . . ? C2 C1 S 107.24(13) . . ? C2 C1 H1A 110.3 . . ? S C1 H1A 110.3 . . ? C2 C1 H1B 110.3 . . ? S C1 H1B 110.3 . . ? H1A C1 H1B 108.5 . . ? C1 C2 C3 117.80(15) . . ? C1 C2 C10 108.32(15) . . ? C3 C2 C10 104.64(15) . . ? C1 C2 C6 118.55(15) . . ? C3 C2 C6 102.20(14) . . ? C10 C2 C6 103.69(14) . . ? C2 C3 C4 102.36(14) . . ? C2 C3 H3A 111.3 . . ? C4 C3 H3A 111.3 . . ? C2 C3 H3B 111.3 . . ? C4 C3 H3B 111.3 . . ? H3A C3 H3B 109.2 . . ? C5 C4 C3 103.39(14) . . ? C5 C4 H4A 111.1 . . ? C3 C4 H4A 111.1 . . ? C5 C4 H4B 111.1 . . ? C3 C4 H4B 111.1 . . ? H4A C4 H4B 109.0 . . ? C9 C5 C6 102.40(14) . . ? C9 C5 C4 107.62(15) . . ? C6 C5 C4 102.84(15) . . ? C9 C5 H5A 114.2 . . ? C6 C5 H5A 114.2 . . ? C4 C5 H5A 114.2 . . ? C7 C6 C8 105.61(16) . . ? C7 C6 C5 114.06(16) . . ? C8 C6 C5 113.47(16) . . ? C7 C6 C2 117.00(15) . . ? C8 C6 C2 114.01(16) . . ? C5 C6 C2 92.76(14) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C5 C9 C10 102.18(15) . . ? C5 C9 H9A 111.3 . . ? C10 C9 H9A 111.3 . . ? C5 C9 H9B 111.3 . . ? C10 C9 H9B 111.3 . . ? H9A C9 H9B 109.2 . . ? N1 C10 C2 106.11(14) . . ? N1 C10 C9 114.88(14) . . ? C2 C10 C9 103.51(14) . . ? N1 C10 H10A 110.7 . . ? C2 C10 H10A 110.7 . . ? C9 C10 H10A 110.7 . . ? O3 C11 N1 120.00(15) . . ? O3 C11 C12 122.62(17) . . ? N1 C11 C12 116.84(15) . . ? N2 C12 C11 111.92(14) . . ? N2 C12 C13 109.47(15) . . ? C11 C12 C13 107.50(13) . . ? N2 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12A 109.3 . . ? C22 C13 C14 108.04(15) . . ? C22 C13 C12 112.82(13) . . ? C14 C13 C12 111.93(15) . . ? C22 C13 H13 108.0 . . ? C14 C13 H13 108.0 . . ? C12 C13 H13 108.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 C16 113.34(17) . . ? O4 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? O4 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C21 C16 C17 118.7(2) . . ? C21 C16 C15 120.36(18) . . ? C17 C16 C15 120.9(2) . . ? C18 C17 C16 120.4(2) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C16 C21 C20 121.1(2) . . ? C16 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C23 C22 C13 116.85(15) . . ? C23 C22 H22A 108.1 . . ? C13 C22 H22A 108.1 . . ? C23 C22 H22B 108.1 . . ? C13 C22 H22B 108.1 . . ? H22A C22 H22B 107.3 . . ? O13 C23 C22 108.13(14) . . ? O13 C23 C24 110.37(14) . . ? C22 C23 C24 111.23(15) . . ? O13 C23 H23 109.0 . . ? C22 C23 H23 109.0 . . ? C24 C23 H23 109.0 . . ? O8 C24 C23 107.56(13) . . ? O8 C24 C25 108.50(13) . . ? C23 C24 C25 111.16(15) . . ? O8 C24 H24 109.9 . . ? C23 C24 H24 109.9 . . ? C25 C24 H24 109.9 . . ? O7 C25 C26 107.83(13) . . ? O7 C25 C24 108.74(14) . . ? C26 C25 C24 112.22(14) . . ? O7 C25 H25 109.3 . . ? C26 C25 H25 109.3 . . ? C24 C25 H25 109.3 . . ? O6 C26 C25 108.03(14) . . ? O6 C26 C27 106.69(14) . . ? C25 C26 C27 110.62(14) . . ? O6 C26 H26 110.5 . . ? C25 C26 H26 110.5 . . ? C27 C26 H26 110.5 . . ? O13 C27 C28 108.59(15) . . ? O13 C27 C26 108.93(15) . . ? C28 C27 C26 113.45(15) . . ? O13 C27 H27 108.6 . . ? C28 C27 H27 108.6 . . ? C26 C27 H27 108.6 . . ? O5 C28 C27 109.91(15) . . ? O5 C28 H28A 109.7 . . ? C27 C28 H28A 109.7 . . ? O5 C28 H28B 109.7 . . ? C27 C28 H28B 109.7 . . ? H28A C28 H28B 108.2 . . ? O9 C29 O5 123.6(2) . . ? O9 C29 C30 125.12(19) . . ? O5 C29 C30 111.24(16) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O12 C31 O6 123.70(18) . . ? O12 C31 C32 124.85(18) . . ? O6 C31 C32 111.40(16) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O11 C33 O7 123.04(16) . . ? O11 C33 C34 126.38(17) . . ? O7 C33 C34 110.58(15) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O10 C35 O8 123.88(17) . . ? O10 C35 C36 124.56(17) . . ? O8 C35 C36 111.56(15) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C11 N1 C10 119.05(14) . . ? C11 N1 S 123.24(12) . . ? C10 N1 S 111.83(12) . . ? O4 N2 C12 107.33(14) . . ? O4 N2 H2 126.3 . . ? C12 N2 H2 126.3 . . ? C15 O4 N2 106.93(13) . . ? C29 O5 C28 117.31(14) . . ? C31 O6 C26 118.42(14) . . ? C33 O7 C25 116.77(13) . . ? C35 O8 C24 116.49(14) . . ? C27 O13 C23 111.32(13) . . ? O1 S O2 117.08(8) . . ? O1 S N1 109.71(8) . . ? O2 S N1 109.47(9) . . ? O1 S C1 112.55(10) . . ? O2 S C1 110.37(10) . . ? N1 S C1 95.50(8) . . ? 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 C17 C18 C19 C20 -1.1(4) . . . . ? C18 C19 C20 C21 0.9(3) . . . . ? S C1 C2 C3 141.72(15) . . . . ? S C1 C2 C10 23.33(17) . . . . ? S C1 C2 C6 -94.31(17) . . . . ? C1 C2 C3 C4 169.42(17) . . . . ? C10 C2 C3 C4 -70.26(17) . . . . ? C6 C2 C3 C4 37.61(19) . . . . ? C2 C3 C4 C5 -2.55(19) . . . . ? C3 C4 C5 C9 73.82(18) . . . . ? C3 C4 C5 C6 -33.85(18) . . . . ? C9 C5 C6 C7 64.39(19) . . . . ? C4 C5 C6 C7 175.98(15) . . . . ? C9 C5 C6 C8 -174.61(16) . . . . ? C4 C5 C6 C8 -63.02(19) . . . . ? C9 C5 C6 C2 -56.90(16) . . . . ? C4 C5 C6 C2 54.69(15) . . . . ? C1 C2 C6 C7 53.2(2) . . . . ? C3 C2 C6 C7 -175.42(17) . . . . ? C10 C2 C6 C7 -66.83(19) . . . . ? C1 C2 C6 C8 -70.7(2) . . . . ? C3 C2 C6 C8 60.70(19) . . . . ? C10 C2 C6 C8 169.29(15) . . . . ? C1 C2 C6 C5 172.09(16) . . . . ? C3 C2 C6 C5 -56.55(16) . . . . ? C10 C2 C6 C5 52.04(15) . . . . ? C6 C5 C9 C10 41.37(17) . . . . ? C4 C5 C9 C10 -66.60(17) . . . . ? C1 C2 C10 N1 -34.42(18) . . . . ? C3 C2 C10 N1 -160.87(14) . . . . ? C6 C2 C10 N1 92.36(15) . . . . ? C1 C2 C10 C9 -155.74(14) . . . . ? C3 C2 C10 C9 77.81(16) . . . . ? C6 C2 C10 C9 -28.96(16) . . . . ? C5 C9 C10 N1 -122.27(16) . . . . ? C5 C9 C10 C2 -7.04(17) . . . . ? O3 C11 C12 N2 -26.4(2) . . . . ? N1 C11 C12 N2 162.01(15) . . . . ? O3 C11 C12 C13 93.8(2) . . . . ? N1 C11 C12 C13 -77.76(19) . . . . ? N2 C12 C13 C22 -61.03(19) . . . . ? C11 C12 C13 C22 177.19(15) . . . . ? N2 C12 C13 C14 61.08(18) . . . . ? C11 C12 C13 C14 -60.69(19) . . . . ? O4 C15 C16 C21 50.4(3) . . . . ? O4 C15 C16 C17 -133.32(19) . . . . ? C19 C18 C17 C16 -0.3(3) . . . . ? C21 C16 C17 C18 1.9(3) . . . . ? C15 C16 C17 C18 -174.44(19) . . . . ? C17 C16 C21 C20 -2.2(3) . . . . ? C15 C16 C21 C20 174.17(19) . . . . ? C19 C20 C21 C16 0.8(3) . . . . ? C14 C13 C22 C23 173.45(16) . . . . ? C12 C13 C22 C23 -62.3(2) . . . . ? C13 C22 C23 O13 -60.2(2) . . . . ? C13 C22 C23 C24 178.42(15) . . . . ? O13 C23 C24 O8 -65.83(18) . . . . ? C22 C23 C24 O8 54.18(19) . . . . ? O13 C23 C24 C25 52.81(19) . . . . ? C22 C23 C24 C25 172.83(15) . . . . ? O8 C24 C25 O7 -47.43(17) . . . . ? C23 C24 C25 O7 -165.51(14) . . . . ? O8 C24 C25 C26 71.77(17) . . . . ? C23 C24 C25 C26 -46.31(19) . . . . ? O7 C25 C26 O6 -75.32(16) . . . . ? C24 C25 C26 O6 164.95(13) . . . . ? O7 C25 C26 C27 168.25(14) . . . . ? C24 C25 C26 C27 48.52(19) . . . . ? O6 C26 C27 O13 -174.77(14) . . . . ? C25 C26 C27 O13 -57.51(18) . . . . ? O6 C26 C27 C28 64.17(19) . . . . ? C25 C26 C27 C28 -178.58(16) . . . . ? O13 C27 C28 O5 -69.04(18) . . . . ? C26 C27 C28 O5 52.2(2) . . . . ? O3 C11 N1 C10 -5.2(3) . . . . ? C12 C11 N1 C10 166.59(15) . . . . ? O3 C11 N1 S 145.54(15) . . . . ? C12 C11 N1 S -42.6(2) . . . . ? C2 C10 N1 C11 -174.54(15) . . . . ? C9 C10 N1 C11 -60.8(2) . . . . ? C2 C10 N1 S 31.56(17) . . . . ? C9 C10 N1 S 145.27(13) . . . . ? C11 C12 N2 O4 -63.94(17) . . . . ? C13 C12 N2 O4 176.98(12) . . . . ? C16 C15 O4 N2 68.9(2) . . . . ? C12 N2 O4 C15 -132.57(15) . . . . ? O9 C29 O5 C28 -0.1(3) . . . . ? C30 C29 O5 C28 179.51(17) . . . . ? C27 C28 O5 C29 124.37(18) . . . . ? O12 C31 O6 C26 -3.0(3) . . . . ? C32 C31 O6 C26 174.72(15) . . . . ? C25 C26 O6 C31 109.24(17) . . . . ? C27 C26 O6 C31 -131.79(16) . . . . ? O11 C33 O7 C25 -12.6(2) . . . . ? C34 C33 O7 C25 166.82(15) . . . . ? C26 C25 O7 C33 150.75(15) . . . . ? C24 C25 O7 C33 -87.33(18) . . . . ? O10 C35 O8 C24 -1.8(2) . . . . ? C36 C35 O8 C24 178.04(13) . . . . ? C23 C24 O8 C35 -136.83(15) . . . . ? C25 C24 O8 C35 102.83(16) . . . . ? C28 C27 O13 C23 -169.72(14) . . . . ? C26 C27 O13 C23 66.28(17) . . . . ? C22 C23 O13 C27 173.78(13) . . . . ? C24 C23 O13 C27 -64.36(18) . . . . ? C11 N1 S O1 74.91(16) . . . . ? C10 N1 S O1 -132.47(13) . . . . ? C11 N1 S O2 -54.84(16) . . . . ? C10 N1 S O2 97.77(14) . . . . ? C11 N1 S C1 -168.74(15) . . . . ? C10 N1 S C1 -16.12(14) . . . . ? C2 C1 S O1 109.12(14) . . . . ? C2 C1 S O2 -118.03(14) . . . . ? C2 C1 S N1 -4.89(14) . . . . ? _diffrn_measured_fraction_theta_max 0.862 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.539 _refine_diff_density_min -0.480 _refine_diff_density_rms 0.054 # Attachment 'RX266_19a_.cif' data_266GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 731616' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C36 H50 N2 O13 S, C H2 Cl2' _chemical_formula_sum 'C37 H52 Cl2 N2 O13 S' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colourless _diffrn_ambient_temperature 100(1) _chemical_formula_weight 835.78 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0031 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 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1495 0.1591 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 7.4542(15) _cell_length_b 23.187(5) _cell_length_c 23.706(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4097.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.160 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1768 _exptl_absorpt_coefficient_mu 0.274 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'X8 Apex II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22600 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.23 _diffrn_reflns_theta_max 26.87 _reflns_number_total 7989 _reflns_number_gt 6544 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXS-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^)+(0.0905P)^2^+9.5409P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.11(13) _refine_ls_number_reflns 7989 _refine_ls_number_parameters 503 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0927 _refine_ls_R_factor_gt 0.0754 _refine_ls_wR_factor_ref 0.1988 _refine_ls_wR_factor_gt 0.1899 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.015 _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 C37 C 0.9421(18) 0.6749(5) 0.0170(5) 0.098(4) Uani 1 1 d . . . H37A H 0.8830 0.6381 0.0111 0.118 Uiso 1 1 calc R . . H37B H 1.0585 0.6731 -0.0012 0.118 Uiso 1 1 calc R . . Cl1 Cl 0.9720(4) 0.68528(13) 0.08809(11) 0.0858(9) Uani 1 1 d . . . Cl2 Cl 0.8145(7) 0.72939(16) -0.01475(14) 0.1344(17) Uani 1 1 d . . . C1 C 0.0685(7) 0.5584(2) 0.29464(19) 0.0182(11) Uani 1 1 d . . . H1A H -0.0513 0.5690 0.2825 0.022 Uiso 1 1 calc R . . H1B H 0.0583 0.5287 0.3232 0.022 Uiso 1 1 calc R . . C2 C 0.1640(6) 0.6104(2) 0.31854(18) 0.0151(10) Uani 1 1 d . . . C3 C 0.1625(7) 0.6174(2) 0.3828(2) 0.0214(11) Uani 1 1 d . . . H3A H 0.2382 0.5888 0.4009 0.026 Uiso 1 1 calc R . . H3B H 0.0418 0.6144 0.3978 0.026 Uiso 1 1 calc R . . C4 C 0.2386(7) 0.6790(2) 0.3910(2) 0.0235(12) Uani 1 1 d . . . H4A H 0.1540 0.7034 0.4109 0.028 Uiso 1 1 calc R . . H4B H 0.3509 0.6782 0.4117 0.028 Uiso 1 1 calc R . . C5 C 0.2673(6) 0.7002(2) 0.3298(2) 0.0166(10) Uani 1 1 d . . . H5 H 0.2717 0.7423 0.3257 0.020 Uiso 1 1 calc R . . C6 C 0.1106(6) 0.6711(2) 0.2981(2) 0.0167(11) Uani 1 1 d . . . C7 C 0.1116(7) 0.6807(2) 0.2337(2) 0.0223(11) Uani 1 1 d . . . H7A H 0.0218 0.6568 0.2165 0.033 Uiso 1 1 calc R . . H7B H 0.2274 0.6708 0.2188 0.033 Uiso 1 1 calc R . . H7C H 0.0863 0.7204 0.2257 0.033 Uiso 1 1 calc R . . C8 C -0.0776(7) 0.6897(3) 0.3188(2) 0.0238(12) Uani 1 1 d . . . H8A H -0.1678 0.6709 0.2965 0.036 Uiso 1 1 calc R . . H8B H -0.0897 0.7307 0.3152 0.036 Uiso 1 1 calc R . . H8C H -0.0919 0.6789 0.3577 0.036 Uiso 1 1 calc R . . C9 C 0.4305(7) 0.6686(2) 0.3056(2) 0.0195(11) Uani 1 1 d . . . H9A H 0.4602 0.6828 0.2682 0.023 Uiso 1 1 calc R . . H9B H 0.5342 0.6728 0.3300 0.023 Uiso 1 1 calc R . . C10 C 0.3668(6) 0.6060(2) 0.3035(2) 0.0163(10) Uani 1 1 d . . . H10 H 0.4292 0.5835 0.3325 0.020 Uiso 1 1 calc R . . C11 C 0.5424(7) 0.5664(2) 0.2230(2) 0.0178(11) Uani 1 1 d . . . C12 C 0.5522(6) 0.5327(2) 0.16741(19) 0.0177(10) Uani 1 1 d . . . H12 H 0.4416 0.5104 0.1625 0.021 Uiso 1 1 calc R . . C13 C 0.5763(6) 0.5742(2) 0.1162(2) 0.0172(11) Uani 1 1 d . . . H13 H 0.7046 0.5831 0.1140 0.021 Uiso 1 1 calc R . . C14 C 0.4799(8) 0.6314(2) 0.1234(2) 0.0253(12) Uani 1 1 d . . . H14A H 0.3542 0.6245 0.1290 0.038 Uiso 1 1 calc R . . H14B H 0.4966 0.6544 0.0901 0.038 Uiso 1 1 calc R . . H14C H 0.5280 0.6513 0.1555 0.038 Uiso 1 1 calc R . . C15 C 0.6172(8) 0.4005(3) 0.1892(2) 0.0287(13) Uani 1 1 d . . . H15A H 0.7064 0.3851 0.1635 0.034 Uiso 1 1 calc R . . H15B H 0.5076 0.4074 0.1682 0.034 Uiso 1 1 calc R . . C16 C 0.5824(7) 0.3582(3) 0.2364(2) 0.0273(12) Uani 1 1 d . . . C17 C 0.4244(8) 0.3278(3) 0.2401(3) 0.0323(14) Uani 1 1 d . . . H17 H 0.3374 0.3324 0.2124 0.039 Uiso 1 1 calc R . . C18 C 0.3929(10) 0.2902(3) 0.2845(3) 0.0445(17) Uani 1 1 d . . . H18 H 0.2865 0.2693 0.2855 0.053 Uiso 1 1 calc R . . C19 C 0.5149(11) 0.2834(3) 0.3268(3) 0.0481(19) Uani 1 1 d . . . H19 H 0.4922 0.2591 0.3572 0.058 Uiso 1 1 calc R . . C20 C 0.6752(12) 0.3141(3) 0.3228(3) 0.054(2) Uani 1 1 d . . . H20 H 0.7612 0.3097 0.3509 0.065 Uiso 1 1 calc R . . C21 C 0.7094(10) 0.3500(3) 0.2795(3) 0.0418(16) Uani 1 1 d . . . H21 H 0.8180 0.3697 0.2781 0.050 Uiso 1 1 calc R . . C22 C 0.5267(6) 0.5444(2) 0.06077(19) 0.0161(10) Uani 1 1 d . . . H22A H 0.5569 0.5700 0.0298 0.019 Uiso 1 1 calc R . . H22B H 0.5998 0.5100 0.0569 0.019 Uiso 1 1 calc R . . C23 C 0.3310(6) 0.5273(2) 0.05529(18) 0.0158(10) Uani 1 1 d . . . H23 H 0.2563 0.5553 0.0754 0.019 Uiso 1 1 calc R . . C24 C 0.2674(6) 0.5229(2) -0.00618(19) 0.0153(10) Uani 1 1 d . . . H24 H 0.3424 0.4953 -0.0268 0.018 Uiso 1 1 calc R . . C25 C 0.0709(7) 0.5040(2) -0.00844(18) 0.0166(10) Uani 1 1 d . . . H25 H -0.0038 0.5332 0.0100 0.020 Uiso 1 1 calc R . . C26 C 0.0507(6) 0.4470(2) 0.02253(18) 0.0126(10) Uani 1 1 d . . . H26 H 0.1144 0.4161 0.0027 0.015 Uiso 1 1 calc R . . C27 C 0.1225(6) 0.4541(2) 0.08253(18) 0.0138(10) Uani 1 1 d . . . H27 H 0.0538 0.4846 0.1013 0.017 Uiso 1 1 calc R . . C28 C 0.1130(7) 0.4003(2) 0.11833(19) 0.0177(11) Uani 1 1 d . . . H28A H 0.1478 0.4097 0.1567 0.021 Uiso 1 1 calc R . . H28B H -0.0098 0.3865 0.1192 0.021 Uiso 1 1 calc R . . C29 C 0.1495(8) 0.3090(2) 0.0718(2) 0.0275(13) Uani 1 1 d . . . C30 C 0.2859(9) 0.2658(2) 0.0546(2) 0.0303(13) Uani 1 1 d . . . H30A H 0.3953 0.2726 0.0749 0.046 Uiso 1 1 calc R . . H30B H 0.3079 0.2691 0.0148 0.046 Uiso 1 1 calc R . . H30C H 0.2426 0.2277 0.0630 0.046 Uiso 1 1 calc R . . C31 C -0.2112(7) 0.3933(2) -0.00611(19) 0.0165(10) Uani 1 1 d . . . C32 C -0.3870(7) 0.3737(2) 0.0171(2) 0.0201(11) Uani 1 1 d . . . H32A H -0.3666 0.3470 0.0475 0.030 Uiso 1 1 calc R . . H32B H -0.4547 0.3550 -0.0121 0.030 Uiso 1 1 calc R . . H32C H -0.4528 0.4063 0.0309 0.030 Uiso 1 1 calc R . . C33 C -0.1181(7) 0.5329(2) -0.0852(2) 0.0220(11) Uani 1 1 d . . . C34 C -0.1573(8) 0.5196(3) -0.1458(2) 0.0290(13) Uani 1 1 d . . . H34A H -0.1896 0.4797 -0.1495 0.044 Uiso 1 1 calc R . . H34B H -0.0526 0.5273 -0.1682 0.044 Uiso 1 1 calc R . . H34C H -0.2547 0.5434 -0.1586 0.044 Uiso 1 1 calc R . . C35 C 0.3603(8) 0.5813(3) -0.0842(2) 0.0337(15) Uani 1 1 d . . . C36 C 0.3701(14) 0.6437(4) -0.1022(4) 0.072(3) Uani 1 1 d . . . H36A H 0.4394 0.6651 -0.0752 0.108 Uiso 1 1 calc R . . H36B H 0.2512 0.6594 -0.1042 0.108 Uiso 1 1 calc R . . H36C H 0.4261 0.6462 -0.1386 0.108 Uiso 1 1 calc R . . N1 N 0.3778(5) 0.57512(18) 0.24826(16) 0.0152(9) Uani 1 1 d . . . N2 N 0.7048(5) 0.49394(19) 0.16676(17) 0.0201(9) Uani 1 1 d . . . H2 H 0.7934 0.4949 0.1436 0.024 Uiso 1 1 calc R . . O1 O 0.2444(5) 0.47367(16) 0.24329(15) 0.0240(8) Uani 1 1 d . . . O2 O 0.1153(4) 0.54828(16) 0.18285(14) 0.0198(8) Uani 1 1 d . . . O3 O 0.6778(4) 0.58674(16) 0.24402(15) 0.0222(8) Uani 1 1 d . . . O4 O 0.6795(5) 0.45266(16) 0.21316(14) 0.0231(8) Uani 1 1 d . . . O5 O 0.2285(5) 0.35491(15) 0.09717(14) 0.0206(8) Uani 1 1 d . . . O6 O -0.1377(4) 0.43288(15) 0.02899(13) 0.0155(7) Uani 1 1 d . . . O7 O 0.0161(5) 0.49786(16) -0.06600(13) 0.0193(8) Uani 1 1 d . . . O8 O 0.2802(5) 0.57904(17) -0.03185(15) 0.0248(8) Uani 1 1 d . . . O9 O -0.0087(6) 0.30513(18) 0.06466(19) 0.0388(11) Uani 1 1 d . . . O10 O 0.4145(6) 0.5407(2) -0.10779(16) 0.0431(12) Uani 1 1 d . . . O11 O -0.1866(6) 0.5688(2) -0.05645(18) 0.0401(11) Uani 1 1 d . . . O12 O -0.1400(5) 0.37686(17) -0.04854(15) 0.0239(9) Uani 1 1 d . . . O13 O 0.3074(4) 0.47165(15) 0.07978(13) 0.0162(7) Uani 1 1 d . . . S S 0.19570(15) 0.53248(6) 0.23621(5) 0.0161(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C37 0.120(10) 0.072(7) 0.102(8) -0.049(6) -0.036(7) 0.044(7) Cl1 0.0750(16) 0.110(2) 0.0729(15) 0.0376(15) -0.0156(13) -0.0265(15) Cl2 0.206(4) 0.113(3) 0.084(2) -0.0163(18) -0.059(2) 0.072(3) C1 0.015(2) 0.028(3) 0.012(2) -0.003(2) 0.0031(18) -0.009(2) C2 0.014(2) 0.019(3) 0.012(2) -0.0064(18) -0.0010(17) -0.0005(19) C3 0.021(3) 0.030(3) 0.014(2) -0.005(2) 0.0028(19) 0.003(2) C4 0.021(3) 0.032(3) 0.018(2) -0.014(2) -0.0031(19) 0.005(2) C5 0.010(2) 0.015(3) 0.024(2) -0.0063(19) -0.0006(18) 0.0012(19) C6 0.011(2) 0.025(3) 0.013(2) -0.0002(19) 0.0020(18) -0.001(2) C7 0.022(2) 0.029(3) 0.015(2) -0.005(2) 0.000(2) 0.004(2) C8 0.016(2) 0.031(4) 0.024(3) -0.013(2) 0.001(2) 0.007(2) C9 0.012(2) 0.028(3) 0.019(2) -0.013(2) -0.0011(19) 0.001(2) C10 0.013(2) 0.021(3) 0.015(2) -0.0074(19) 0.0001(18) 0.003(2) C11 0.018(2) 0.015(3) 0.020(2) -0.0038(19) 0.0004(19) 0.000(2) C12 0.013(2) 0.024(3) 0.017(2) -0.007(2) 0.0039(18) -0.004(2) C13 0.013(2) 0.020(3) 0.019(2) -0.005(2) 0.0038(18) -0.007(2) C14 0.033(3) 0.025(3) 0.018(2) -0.003(2) 0.002(2) -0.004(2) C15 0.024(3) 0.038(4) 0.025(3) -0.011(2) -0.002(2) 0.004(3) C16 0.030(3) 0.027(3) 0.025(3) -0.015(2) 0.001(2) 0.008(2) C17 0.037(3) 0.030(4) 0.030(3) -0.008(3) -0.001(3) -0.001(3) C18 0.052(4) 0.028(4) 0.054(4) 0.000(3) 0.003(3) -0.009(3) C19 0.078(6) 0.022(4) 0.044(4) 0.005(3) -0.011(4) 0.010(4) C20 0.069(5) 0.036(5) 0.057(5) -0.002(3) -0.025(4) 0.008(4) C21 0.039(4) 0.034(4) 0.052(4) -0.009(3) -0.009(3) 0.008(3) C22 0.016(2) 0.020(3) 0.012(2) -0.0040(18) 0.0038(17) 0.000(2) C23 0.016(2) 0.021(3) 0.011(2) -0.0063(19) 0.0023(17) 0.000(2) C24 0.019(2) 0.012(3) 0.014(2) -0.0034(18) -0.0001(18) -0.001(2) C25 0.022(2) 0.022(3) 0.006(2) -0.0043(19) 0.0007(18) 0.003(2) C26 0.014(2) 0.012(3) 0.012(2) -0.0003(17) 0.0010(17) -0.0011(18) C27 0.010(2) 0.019(3) 0.012(2) -0.0039(18) -0.0002(17) 0.0005(18) C28 0.021(2) 0.026(3) 0.006(2) -0.0008(19) 0.0037(18) -0.004(2) C29 0.041(3) 0.018(3) 0.023(3) 0.009(2) -0.009(2) -0.010(3) C30 0.049(4) 0.017(3) 0.024(3) -0.003(2) 0.010(3) -0.005(3) C31 0.021(2) 0.016(3) 0.012(2) 0.0020(18) -0.0006(19) 0.001(2) C32 0.019(3) 0.022(3) 0.019(2) -0.004(2) 0.0017(19) -0.003(2) C33 0.022(2) 0.022(3) 0.022(2) 0.004(2) -0.004(2) -0.002(2) C34 0.027(3) 0.037(4) 0.024(3) -0.003(2) -0.003(2) 0.011(2) C35 0.027(3) 0.049(5) 0.025(3) 0.012(3) 0.004(2) -0.010(3) C36 0.088(7) 0.070(6) 0.058(5) 0.037(5) 0.033(5) 0.003(5) N1 0.0108(18) 0.021(3) 0.0138(19) -0.0070(16) -0.0004(14) 0.0006(16) N2 0.013(2) 0.026(3) 0.022(2) -0.0048(18) 0.0075(17) 0.0012(18) O1 0.0247(17) 0.021(2) 0.0268(19) -0.0057(15) 0.0061(15) 0.0010(15) O2 0.0163(17) 0.029(2) 0.0136(16) -0.0032(14) -0.0014(13) -0.0033(15) O3 0.0125(16) 0.030(2) 0.0240(18) -0.0126(15) 0.0011(14) -0.0012(15) O4 0.0274(19) 0.021(2) 0.0211(17) -0.0063(14) -0.0018(15) -0.0025(16) O5 0.0243(19) 0.014(2) 0.0232(18) -0.0044(14) 0.0021(15) -0.0013(15) O6 0.0135(16) 0.020(2) 0.0133(15) -0.0060(13) 0.0010(13) 0.0004(13) O7 0.0206(18) 0.025(2) 0.0119(16) -0.0037(14) -0.0029(13) 0.0069(15) O8 0.0252(19) 0.028(2) 0.0217(18) 0.0070(15) 0.0036(15) -0.0038(17) O9 0.044(3) 0.019(3) 0.054(3) 0.0025(19) -0.020(2) -0.0110(19) O10 0.054(3) 0.062(3) 0.0128(18) -0.002(2) 0.0122(18) -0.010(3) O11 0.043(3) 0.043(3) 0.034(2) -0.007(2) -0.009(2) 0.026(2) O12 0.0262(19) 0.028(2) 0.0179(17) -0.0095(15) 0.0019(15) -0.0034(16) O13 0.0172(16) 0.0146(19) 0.0167(16) -0.0014(13) -0.0016(13) 0.0005(14) S 0.0130(5) 0.0217(7) 0.0137(5) -0.0055(5) 0.0027(4) -0.0024(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C37 Cl1 1.717(11) . ? C37 Cl2 1.752(11) . ? C1 C2 1.510(7) . ? C1 S 1.783(5) . ? C2 C3 1.533(6) . ? C2 C6 1.540(8) . ? C2 C10 1.557(6) . ? C3 C4 1.549(8) . ? C4 C5 1.547(7) . ? C5 C9 1.531(7) . ? C5 C6 1.545(7) . ? C6 C7 1.542(7) . ? C6 C8 1.548(6) . ? C9 C10 1.530(8) . ? C10 N1 1.494(6) . ? C11 O3 1.221(6) . ? C11 N1 1.381(6) . ? C11 C12 1.532(6) . ? C12 N2 1.450(6) . ? C12 C13 1.559(7) . ? C13 C14 1.517(8) . ? C13 C22 1.531(6) . ? C15 O4 1.414(7) . ? C15 C16 1.511(9) . ? C16 C17 1.376(8) . ? C16 C21 1.406(9) . ? C17 C18 1.387(9) . ? C18 C19 1.362(10) . ? C19 C20 1.395(12) . ? C20 C21 1.345(11) . ? C22 C23 1.517(6) . ? C23 O13 1.426(6) . ? C23 C24 1.536(6) . ? C24 O8 1.440(6) . ? C24 C25 1.530(7) . ? C25 O7 1.431(5) . ? C25 C26 1.519(7) . ? C26 O6 1.450(6) . ? C26 C27 1.529(6) . ? C27 O13 1.438(5) . ? C27 C28 1.510(7) . ? C28 O5 1.449(6) . ? C29 O9 1.195(7) . ? C29 O5 1.356(7) . ? C29 C30 1.485(9) . ? C31 O12 1.199(6) . ? C31 O6 1.355(6) . ? C31 C32 1.493(7) . ? C33 O11 1.192(7) . ? C33 O7 1.367(6) . ? C33 C34 1.497(7) . ? C35 O10 1.168(8) . ? C35 O8 1.379(7) . ? C35 C36 1.510(11) . ? N1 S 1.703(4) . ? N2 O4 1.470(6) . ? O1 S 1.421(4) . ? O2 S 1.447(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 Cl1 C37 Cl2 113.0(5) . . ? C2 C1 S 108.1(3) . . ? C1 C2 C3 117.0(4) . . ? C1 C2 C6 119.3(4) . . ? C3 C2 C6 102.4(4) . . ? C1 C2 C10 108.6(4) . . ? C3 C2 C10 104.0(4) . . ? C6 C2 C10 103.8(4) . . ? C2 C3 C4 102.7(4) . . ? C5 C4 C3 103.1(4) . . ? C9 C5 C6 102.1(4) . . ? C9 C5 C4 108.0(4) . . ? C6 C5 C4 102.2(4) . . ? C2 C6 C7 116.2(4) . . ? C2 C6 C5 93.0(4) . . ? C7 C6 C5 114.5(4) . . ? C2 C6 C8 112.9(4) . . ? C7 C6 C8 106.2(4) . . ? C5 C6 C8 114.1(4) . . ? C10 C9 C5 102.8(4) . . ? N1 C10 C9 117.8(4) . . ? N1 C10 C2 106.6(4) . . ? C9 C10 C2 103.3(4) . . ? O3 C11 N1 120.0(4) . . ? O3 C11 C12 120.6(4) . . ? N1 C11 C12 119.4(4) . . ? N2 C12 C11 111.2(4) . . ? N2 C12 C13 106.5(4) . . ? C11 C12 C13 111.1(4) . . ? C14 C13 C22 112.1(4) . . ? C14 C13 C12 113.4(4) . . ? C22 C13 C12 111.2(4) . . ? O4 C15 C16 108.3(4) . . ? C17 C16 C21 117.4(6) . . ? C17 C16 C15 121.8(5) . . ? C21 C16 C15 120.7(6) . . ? C16 C17 C18 121.1(6) . . ? C19 C18 C17 121.2(7) . . ? C18 C19 C20 117.5(7) . . ? C21 C20 C19 122.1(7) . . ? C20 C21 C16 120.7(7) . . ? C23 C22 C13 115.1(4) . . ? O13 C23 C22 108.7(4) . . ? O13 C23 C24 106.7(4) . . ? C22 C23 C24 113.3(4) . . ? O8 C24 C25 107.9(4) . . ? O8 C24 C23 108.7(4) . . ? C25 C24 C23 110.4(4) . . ? O7 C25 C26 110.3(4) . . ? O7 C25 C24 109.6(4) . . ? C26 C25 C24 109.1(4) . . ? O6 C26 C25 110.1(4) . . ? O6 C26 C27 105.4(3) . . ? C25 C26 C27 108.7(4) . . ? O13 C27 C28 107.7(4) . . ? O13 C27 C26 108.9(3) . . ? C28 C27 C26 114.6(4) . . ? O5 C28 C27 112.2(4) . . ? O9 C29 O5 123.4(6) . . ? O9 C29 C30 125.9(6) . . ? O5 C29 C30 110.7(5) . . ? O12 C31 O6 123.5(5) . . ? O12 C31 C32 126.9(5) . . ? O6 C31 C32 109.6(4) . . ? O11 C33 O7 122.5(5) . . ? O11 C33 C34 127.5(5) . . ? O7 C33 C34 109.9(5) . . ? O10 C35 O8 123.4(6) . . ? O10 C35 C36 128.4(6) . . ? O8 C35 C36 108.2(6) . . ? C11 N1 C10 120.0(4) . . ? C11 N1 S 123.4(3) . . ? C10 N1 S 112.4(3) . . ? C12 N2 O4 107.2(3) . . ? C15 O4 N2 107.3(4) . . ? C29 O5 C28 117.7(4) . . ? C31 O6 C26 118.6(4) . . ? C33 O7 C25 117.9(4) . . ? C35 O8 C24 116.3(4) . . ? C23 O13 C27 113.1(4) . . ? O1 S O2 116.9(2) . . ? O1 S N1 109.5(2) . . ? O2 S N1 109.3(2) . . ? O1 S C1 111.6(2) . . ? O2 S C1 111.9(2) . . ? N1 S C1 95.6(2) . . ? _diffrn_measured_fraction_theta_max 0.921 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.959 _refine_diff_density_max 0.528 _refine_diff_density_min -0.869 _refine_diff_density_rms 0.097 # Attachment 'RX302_16a_NEW.cif' data_302GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 731617' _audit_update_record ; 2009-07-16 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C36 H50 N2 O13 S' _chemical_formula_sum 'C36 H50 N2 O13 S' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 100(1) _chemical_formula_weight 750.85 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 12.629(5) _cell_length_b 14.954(5) _cell_length_c 20.739(5) _cell_angle_alpha 90. _cell_angle_beta 90. _cell_angle_gamma 90. _cell_volume 3917(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_size_max 0.230 _exptl_crystal_size_mid 0.210 _exptl_crystal_size_min 0.060 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.147 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.988 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71069 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'kappa X8 APEX II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 35511 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0602 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 30.67 _reflns_number_total 11061 _reflns_number_gt 8682 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0671P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(5) _refine_ls_number_reflns 11061 _refine_ls_number_parameters 469 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1178 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.006 _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 0.55904(16) 0.00511(11) 0.09915(10) 0.0303(4) Uani 1 1 d . . . H1A H 0.5765 0.0010 0.1446 0.036 Uiso 1 1 calc R . . H1B H 0.6121 0.0418 0.0780 0.036 Uiso 1 1 calc R . . C2 C 0.45030(15) 0.04605(12) 0.09062(9) 0.0259(4) Uani 1 1 d . . . C3 C 0.40509(18) 0.10207(13) 0.14673(10) 0.0355(5) Uani 1 1 d . . . H3A H 0.4550 0.1474 0.1606 0.043 Uiso 1 1 calc R . . H3B H 0.3866 0.0646 0.1832 0.043 Uiso 1 1 calc R . . C4 C 0.30510(18) 0.14484(14) 0.11591(11) 0.0398(5) Uani 1 1 d . . . H4A H 0.2412 0.1237 0.1369 0.048 Uiso 1 1 calc R . . H4B H 0.3077 0.2095 0.1187 0.048 Uiso 1 1 calc R . . C5 C 0.30942(16) 0.11380(13) 0.04544(11) 0.0339(4) Uani 1 1 d . . . H5 H 0.2697 0.1516 0.0153 0.041 Uiso 1 1 calc R . . C6 C 0.43039(16) 0.10902(12) 0.03184(9) 0.0291(4) Uani 1 1 d . . . C7 C 0.45919(19) 0.07150(14) -0.03472(10) 0.0371(5) Uani 1 1 d . . . H7A H 0.5344 0.0631 -0.0373 0.056 Uiso 1 1 calc R . . H7B H 0.4369 0.1127 -0.0675 0.056 Uiso 1 1 calc R . . H7C H 0.4242 0.0152 -0.0410 0.056 Uiso 1 1 calc R . . C8 C 0.48812(18) 0.19908(13) 0.03841(12) 0.0392(5) Uani 1 1 d . . . H8A H 0.5630 0.1889 0.0411 0.059 Uiso 1 1 calc R . . H8B H 0.4644 0.2290 0.0768 0.059 Uiso 1 1 calc R . . H8C H 0.4729 0.2356 0.0015 0.059 Uiso 1 1 calc R . . C9 C 0.27752(17) 0.01405(13) 0.04444(11) 0.0365(5) Uani 1 1 d . . . H9A H 0.2106 0.0045 0.0663 0.044 Uiso 1 1 calc R . . H9B H 0.2723 -0.0083 0.0006 0.044 Uiso 1 1 calc R . . C10 C 0.36945(15) -0.03092(12) 0.08106(9) 0.0262(4) Uani 1 1 d . . . H10 H 0.3453 -0.0541 0.1227 0.031 Uiso 1 1 calc R . . C11 C 0.37046(15) -0.17713(12) 0.02470(8) 0.0223(4) Uani 1 1 d . . . C12 C 0.42119(14) -0.23492(11) -0.02796(8) 0.0212(3) Uani 1 1 d . . . H12 H 0.4973 -0.2403 -0.0196 0.025 Uiso 1 1 calc R . . C13 C 0.40370(14) -0.18577(11) -0.09340(8) 0.0218(4) Uani 1 1 d . . . H13 H 0.4363 -0.1265 -0.0900 0.026 Uiso 1 1 calc R . . C14 C 0.28605(15) -0.17240(13) -0.10883(9) 0.0272(4) Uani 1 1 d . . . H14A H 0.2527 -0.1407 -0.0741 0.041 Uiso 1 1 calc R . . H14B H 0.2527 -0.2296 -0.1142 0.041 Uiso 1 1 calc R . . H14C H 0.2791 -0.1385 -0.1479 0.041 Uiso 1 1 calc R . . C15 C 0.48485(17) -0.44295(12) -0.00483(9) 0.0296(4) Uani 1 1 d . . . H15A H 0.5228 -0.4723 0.0299 0.036 Uiso 1 1 calc R . . H15B H 0.5367 -0.4144 -0.0325 0.036 Uiso 1 1 calc R . . C16 C 0.42569(16) -0.51240(12) -0.04325(9) 0.0276(4) Uani 1 1 d . . . C17 C 0.37156(17) -0.58052(12) -0.01230(10) 0.0305(4) Uani 1 1 d . . . H17 H 0.3743 -0.5849 0.0324 0.037 Uiso 1 1 calc R . . C18 C 0.31326(16) -0.64226(13) -0.04736(10) 0.0331(4) Uani 1 1 d . . . H18 H 0.2762 -0.6871 -0.0260 0.040 Uiso 1 1 calc R . . C19 C 0.31013(19) -0.63730(14) -0.11398(11) 0.0398(5) Uani 1 1 d . . . H19 H 0.2714 -0.6789 -0.1375 0.048 Uiso 1 1 calc R . . C20 C 0.3648(2) -0.57030(14) -0.14514(11) 0.0419(5) Uani 1 1 d . . . H20 H 0.3628 -0.5665 -0.1899 0.050 Uiso 1 1 calc R . . C21 C 0.42300(19) -0.50824(13) -0.10974(10) 0.0364(5) Uani 1 1 d . . . H21 H 0.4604 -0.4636 -0.1311 0.044 Uiso 1 1 calc R . . C22 C 0.45627(13) -0.23447(12) -0.14969(8) 0.0216(3) Uani 1 1 d . . . H22A H 0.4334 -0.2964 -0.1493 0.026 Uiso 1 1 calc R . . H22B H 0.4316 -0.2080 -0.1897 0.026 Uiso 1 1 calc R . . C23 C 0.57601(13) -0.23230(11) -0.14918(8) 0.0200(3) Uani 1 1 d . . . H23 H 0.6030 -0.2640 -0.1112 0.024 Uiso 1 1 calc R . . C24 C 0.62429(14) -0.27201(11) -0.21057(8) 0.0215(4) Uani 1 1 d . . . H24 H 0.5967 -0.2405 -0.2484 0.026 Uiso 1 1 calc R . . C25 C 0.74441(13) -0.26431(11) -0.20880(8) 0.0208(3) Uani 1 1 d . . . H25 H 0.7736 -0.3049 -0.1762 0.025 Uiso 1 1 calc R . . C26 C 0.77725(13) -0.16912(12) -0.19439(8) 0.0206(3) Uani 1 1 d . . . H26 H 0.7652 -0.1312 -0.2322 0.025 Uiso 1 1 calc R . . C27 C 0.71865(13) -0.13112(11) -0.13588(8) 0.0203(3) Uani 1 1 d . . . H27 H 0.7379 -0.1660 -0.0976 0.024 Uiso 1 1 calc R . . C28 C 0.74264(14) -0.03418(11) -0.12351(8) 0.0223(4) Uani 1 1 d . . . H28A H 0.7005 -0.0128 -0.0876 0.027 Uiso 1 1 calc R . . H28B H 0.8168 -0.0272 -0.1124 0.027 Uiso 1 1 calc R . . C29 C 0.77651(16) 0.09272(12) -0.18904(9) 0.0279(4) Uani 1 1 d . . . C30 C 0.7512(2) 0.13751(14) -0.25127(11) 0.0426(5) Uani 1 1 d . . . H30A H 0.7024 0.1856 -0.2437 0.064 Uiso 1 1 calc R . . H30B H 0.7200 0.0950 -0.2803 0.064 Uiso 1 1 calc R . . H30C H 0.8151 0.1609 -0.2699 0.064 Uiso 1 1 calc R . . C31 C 0.95206(14) -0.10970(12) -0.20562(8) 0.0243(4) Uani 1 1 d . . . C32 C 1.06384(15) -0.12402(14) -0.18420(10) 0.0306(4) Uani 1 1 d . . . H32A H 1.1074 -0.0761 -0.1999 0.046 Uiso 1 1 calc R . . H32B H 1.0893 -0.1799 -0.2010 0.046 Uiso 1 1 calc R . . H32C H 1.0666 -0.1253 -0.1379 0.046 Uiso 1 1 calc R . . C33 C 0.82811(16) -0.36728(13) -0.28211(10) 0.0304(4) Uani 1 1 d . . . C34 C 0.8738(2) -0.37479(15) -0.34839(11) 0.0444(6) Uani 1 1 d . . . H34A H 0.8528 -0.3239 -0.3735 0.067 Uiso 1 1 calc R . . H34B H 0.8482 -0.4284 -0.3685 0.067 Uiso 1 1 calc R . . H34C H 0.9496 -0.3769 -0.3457 0.067 Uiso 1 1 calc R . . C35 C 0.5612(2) -0.39631(17) -0.27095(11) 0.0551(7) Uani 1 1 d . . . N1 N 0.42609(11) -0.10103(10) 0.04417(7) 0.0225(3) Uani 1 1 d . . . N2 N 0.37431(13) -0.32389(10) -0.03121(7) 0.0244(3) Uani 1 1 d . . . H2 H 0.3297 -0.3423 -0.0596 0.029 Uiso 1 1 calc R . . O1 O 0.61864(11) -0.11025(10) 0.00653(7) 0.0353(3) Uani 1 1 d . . . O2 O 0.57251(12) -0.17089(9) 0.11204(7) 0.0341(3) Uani 1 1 d . . . O3 O 0.28026(11) -0.18925(8) 0.04318(6) 0.0280(3) Uani 1 1 d . . . O4 O 0.41656(11) -0.37558(8) 0.02200(6) 0.0285(3) Uani 1 1 d . . . O5 O 0.71875(10) 0.01737(8) -0.18050(6) 0.0254(3) Uani 1 1 d . . . O6 O 0.88878(9) -0.17286(8) -0.17963(6) 0.0231(3) Uani 1 1 d . . . O7 O 0.78818(10) -0.28494(8) -0.27152(6) 0.0249(3) Uani 1 1 d . . . O8 O 0.59758(10) -0.36606(8) -0.21459(6) 0.0272(3) Uani 1 1 d . . . O9 O 0.84058(12) 0.11915(9) -0.15064(7) 0.0361(3) Uani 1 1 d . . . O10 O 0.5327(4) -0.34752(18) -0.31248(12) 0.0440(6) Uani 1 1 d . . . O11 O 0.82380(14) -0.42707(10) -0.24393(7) 0.0442(4) Uani 1 1 d . . . O13 O 0.60758(9) -0.14035(7) -0.14708(6) 0.0208(3) Uani 1 1 d . . . O96 O 0.92118(11) -0.05073(9) -0.24043(7) 0.0338(3) Uani 1 1 d . . . S S 0.55607(4) -0.10396(3) 0.06387(2) 0.02399(10) Uani 1 1 d . . . C36 C 0.5548(2) -0.49507(15) -0.27367(14) 0.0554(7) Uani 1 1 d . . . H36A H 0.4906 -0.5124 -0.2950 0.083 Uiso 1 1 calc R . . H36B H 0.5552 -0.5188 -0.2307 0.083 Uiso 1 1 calc R . . H36C H 0.6145 -0.5180 -0.2971 0.083 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 C1 0.0350(10) 0.0209(9) 0.0352(10) -0.0053(8) -0.0105(9) -0.0018(8) C2 0.0293(10) 0.0203(8) 0.0280(9) -0.0027(7) -0.0019(8) -0.0013(7) C3 0.0522(12) 0.0221(9) 0.0321(10) -0.0069(8) 0.0034(9) -0.0014(9) C4 0.0453(13) 0.0220(10) 0.0521(13) -0.0097(9) 0.0035(11) 0.0018(9) C5 0.0334(10) 0.0231(10) 0.0452(11) -0.0038(9) -0.0064(9) 0.0047(8) C6 0.0355(10) 0.0198(9) 0.0319(9) 0.0019(7) -0.0023(8) -0.0002(8) C7 0.0508(14) 0.0299(10) 0.0307(10) 0.0070(8) 0.0000(9) 0.0029(9) C8 0.0425(12) 0.0231(10) 0.0520(13) 0.0063(9) -0.0026(10) -0.0031(8) C9 0.0330(11) 0.0249(10) 0.0517(13) -0.0083(9) -0.0026(10) 0.0008(8) C10 0.0322(10) 0.0172(8) 0.0293(9) -0.0036(7) 0.0057(8) 0.0015(7) C11 0.0285(10) 0.0161(8) 0.0224(8) 0.0024(7) 0.0004(7) -0.0005(7) C12 0.0239(9) 0.0180(8) 0.0219(8) -0.0010(6) 0.0019(7) -0.0024(7) C13 0.0226(9) 0.0195(8) 0.0234(8) 0.0003(7) 0.0012(7) -0.0021(7) C14 0.0230(9) 0.0311(10) 0.0274(9) 0.0025(8) 0.0007(8) 0.0012(7) C15 0.0378(11) 0.0219(9) 0.0290(10) 0.0016(8) -0.0036(8) 0.0034(8) C16 0.0346(10) 0.0193(9) 0.0288(9) -0.0015(7) -0.0006(8) 0.0059(7) C17 0.0411(11) 0.0229(9) 0.0275(9) 0.0002(8) 0.0020(8) 0.0071(8) C18 0.0369(11) 0.0217(9) 0.0409(11) 0.0023(8) 0.0049(9) 0.0020(8) C19 0.0513(13) 0.0288(11) 0.0392(12) -0.0079(9) -0.0045(10) -0.0027(10) C20 0.0652(15) 0.0310(11) 0.0297(10) -0.0028(9) -0.0056(10) -0.0059(10) C21 0.0520(13) 0.0258(10) 0.0313(10) -0.0004(8) 0.0020(10) -0.0049(9) C22 0.0212(9) 0.0226(8) 0.0211(8) -0.0002(7) -0.0033(7) -0.0016(7) C23 0.0219(8) 0.0168(8) 0.0212(8) 0.0000(6) -0.0028(7) -0.0017(6) C24 0.0246(9) 0.0184(8) 0.0215(8) -0.0007(7) 0.0002(7) -0.0024(7) C25 0.0220(9) 0.0203(8) 0.0202(8) 0.0007(7) 0.0018(7) 0.0009(7) C26 0.0157(8) 0.0232(8) 0.0230(8) 0.0027(7) -0.0006(7) 0.0013(7) C27 0.0201(8) 0.0202(8) 0.0205(8) 0.0009(7) -0.0025(7) -0.0008(7) C28 0.0230(9) 0.0213(8) 0.0224(8) 0.0009(7) -0.0010(7) -0.0014(7) C29 0.0325(10) 0.0197(9) 0.0316(10) 0.0011(8) -0.0004(8) -0.0029(8) C30 0.0579(14) 0.0284(11) 0.0415(12) 0.0090(9) -0.0043(11) -0.0088(10) C31 0.0237(9) 0.0238(9) 0.0255(9) 0.0000(7) 0.0030(7) -0.0013(7) C32 0.0236(9) 0.0349(10) 0.0334(10) 0.0073(8) -0.0022(8) -0.0043(8) C33 0.0335(10) 0.0249(10) 0.0326(10) 0.0006(8) 0.0057(8) 0.0044(8) C34 0.0622(15) 0.0327(11) 0.0383(12) 0.0006(9) 0.0205(11) 0.0066(11) C35 0.092(2) 0.0425(13) 0.0310(11) -0.0152(11) 0.0076(13) -0.0276(14) N1 0.0246(7) 0.0190(7) 0.0237(7) -0.0023(6) 0.0014(6) 0.0004(6) N2 0.0338(9) 0.0182(7) 0.0212(7) -0.0002(6) -0.0062(6) -0.0024(6) O1 0.0277(7) 0.0428(8) 0.0356(8) -0.0064(7) 0.0041(6) -0.0063(6) O2 0.0395(8) 0.0254(7) 0.0376(8) 0.0051(6) -0.0069(7) 0.0047(6) O3 0.0307(7) 0.0217(6) 0.0316(7) -0.0006(5) 0.0077(6) -0.0030(5) O4 0.0442(8) 0.0201(6) 0.0212(6) 0.0011(5) 0.0016(6) -0.0007(5) O5 0.0288(7) 0.0190(6) 0.0283(6) 0.0032(5) -0.0054(6) -0.0010(5) O6 0.0163(6) 0.0243(6) 0.0286(6) 0.0044(5) -0.0017(5) -0.0015(5) O7 0.0307(7) 0.0227(6) 0.0214(6) -0.0002(5) 0.0055(5) 0.0032(5) O8 0.0287(7) 0.0197(6) 0.0331(7) -0.0064(5) -0.0006(6) -0.0037(5) O9 0.0457(8) 0.0297(7) 0.0329(7) 0.0032(6) -0.0044(7) -0.0122(6) O10 0.0770(12) 0.0296(9) 0.0355(8) 0.0057(9) 0.0171(7) -0.0069(8) O11 0.0650(10) 0.0326(8) 0.0350(8) 0.0053(7) 0.0157(8) 0.0169(7) O13 0.0215(6) 0.0171(6) 0.0239(6) 0.0003(5) -0.0006(5) -0.0026(5) O96 0.0277(7) 0.0313(7) 0.0424(8) 0.0147(6) 0.0039(6) 0.0012(6) S 0.0263(2) 0.0199(2) 0.0257(2) -0.00188(17) -0.00228(18) -0.00017(17) C36 0.0461(14) 0.0451(14) 0.0749(17) -0.0359(13) 0.0215(13) -0.0189(12) _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 1.514(3) . ? C1 S 1.7881(18) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.543(3) . ? C2 C10 1.551(3) . ? C2 C6 1.561(3) . ? C3 C4 1.553(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.534(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C9 1.545(3) . ? C5 C6 1.555(3) . ? C5 H5 0.9800 . ? C6 C7 1.534(3) . ? C6 C8 1.537(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.542(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 N1 1.482(2) . ? C10 H10 0.9800 . ? C11 O3 1.216(2) . ? C11 N1 1.397(2) . ? C11 C12 1.533(2) . ? C12 N2 1.458(2) . ? C12 C13 1.559(2) . ? C12 H12 0.9800 . ? C13 C22 1.528(2) . ? C13 C14 1.533(3) . ? C13 H13 0.9800 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 O4 1.438(2) . ? C15 C16 1.507(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C21 1.381(3) . ? C16 C17 1.385(3) . ? C17 C18 1.387(3) . ? C17 H17 0.9300 . ? C18 C19 1.384(3) . ? C18 H18 0.9300 . ? C19 C20 1.378(3) . ? C19 H19 0.9300 . ? C20 C21 1.393(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? C22 C23 1.513(2) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 O13 1.432(2) . ? C23 C24 1.532(2) . ? C23 H23 0.9800 . ? C24 O8 1.449(2) . ? C24 C25 1.522(3) . ? C24 H24 0.9800 . ? C25 O7 1.447(2) . ? C25 C26 1.512(2) . ? C25 H25 0.9800 . ? C26 O6 1.442(2) . ? C26 C27 1.531(2) . ? C26 H26 0.9800 . ? C27 O13 1.428(2) . ? C27 C28 1.503(2) . ? C27 H27 0.9800 . ? C28 O5 1.443(2) . ? C28 H28A 0.9700 . ? C28 H28B 0.9700 . ? C29 O9 1.202(2) . ? C29 O5 1.354(2) . ? C29 C30 1.489(3) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 O96 1.205(2) . ? C31 O6 1.349(2) . ? C31 C32 1.495(3) . ? C32 H32A 0.9600 . ? C32 H32B 0.9600 . ? C32 H32C 0.9600 . ? C33 O11 1.196(2) . ? C33 O7 1.349(2) . ? C33 C34 1.495(3) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 O10 1.185(4) . ? C35 O8 1.335(3) . ? C35 C36 1.480(3) . ? N1 S 1.6923(16) . ? N2 O4 1.4492(19) . ? N2 H2 0.8600 . ? O1 S 1.4307(15) . ? O2 S 1.4293(14) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 S 107.58(13) . . ? C2 C1 H1A 110.2 . . ? S C1 H1A 110.2 . . ? C2 C1 H1B 110.2 . . ? S C1 H1B 110.2 . . ? H1A C1 H1B 108.5 . . ? C1 C2 C3 117.84(16) . . ? C1 C2 C10 108.18(15) . . ? C3 C2 C10 104.81(15) . . ? C1 C2 C6 118.78(16) . . ? C3 C2 C6 101.64(15) . . ? C10 C2 C6 103.99(14) . . ? C2 C3 C4 102.36(16) . . ? C2 C3 H3A 111.3 . . ? C4 C3 H3A 111.3 . . ? C2 C3 H3B 111.3 . . ? C4 C3 H3B 111.3 . . ? H3A C3 H3B 109.2 . . ? C5 C4 C3 103.80(16) . . ? C5 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? C5 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? C4 C5 C9 107.20(18) . . ? C4 C5 C6 102.80(16) . . ? C9 C5 C6 102.08(15) . . ? C4 C5 H5 114.5 . . ? C9 C5 H5 114.5 . . ? C6 C5 H5 114.5 . . ? C7 C6 C8 106.72(17) . . ? C7 C6 C5 114.40(17) . . ? C8 C6 C5 114.17(16) . . ? C7 C6 C2 116.36(15) . . ? C8 C6 C2 112.51(16) . . ? C5 C6 C2 92.54(15) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C5 102.59(16) . . ? C10 C9 H9A 111.2 . . ? C5 C9 H9A 111.2 . . ? C10 C9 H9B 111.2 . . ? C5 C9 H9B 111.2 . . ? H9A C9 H9B 109.2 . . ? N1 C10 C9 114.69(16) . . ? N1 C10 C2 105.86(14) . . ? C9 C10 C2 103.60(14) . . ? N1 C10 H10 110.8 . . ? C9 C10 H10 110.8 . . ? C2 C10 H10 110.8 . . ? O3 C11 N1 120.10(16) . . ? O3 C11 C12 122.16(16) . . ? N1 C11 C12 117.06(15) . . ? N2 C12 C11 112.19(14) . . ? N2 C12 C13 109.41(14) . . ? C11 C12 C13 107.17(14) . . ? N2 C12 H12 109.3 . . ? C11 C12 H12 109.3 . . ? C13 C12 H12 109.3 . . ? C22 C13 C14 108.89(14) . . ? C22 C13 C12 112.26(14) . . ? C14 C13 C12 112.37(14) . . ? C22 C13 H13 107.7 . . ? C14 C13 H13 107.7 . . ? C12 C13 H13 107.7 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 C16 112.95(16) . . ? O4 C15 H15A 109.0 . . ? C16 C15 H15A 109.0 . . ? O4 C15 H15B 109.0 . . ? C16 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? C21 C16 C17 118.95(19) . . ? C21 C16 C15 120.60(18) . . ? C17 C16 C15 120.45(17) . . ? C16 C17 C18 120.59(19) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C19 C18 C17 120.2(2) . . ? C19 C18 H18 119.9 . . ? C17 C18 H18 119.9 . . ? C20 C19 C18 119.5(2) . . ? C20 C19 H19 120.2 . . ? C18 C19 H19 120.2 . . ? C19 C20 C21 120.1(2) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C16 C21 C20 120.6(2) . . ? C16 C21 H21 119.7 . . ? C20 C21 H21 119.7 . . ? C23 C22 C13 114.76(14) . . ? C23 C22 H22A 108.6 . . ? C13 C22 H22A 108.6 . . ? C23 C22 H22B 108.6 . . ? C13 C22 H22B 108.6 . . ? H22A C22 H22B 107.6 . . ? O13 C23 C22 107.41(13) . . ? O13 C23 C24 106.66(13) . . ? C22 C23 C24 112.57(14) . . ? O13 C23 H23 110.0 . . ? C22 C23 H23 110.0 . . ? C24 C23 H23 110.0 . . ? O8 C24 C25 107.88(14) . . ? O8 C24 C23 109.37(14) . . ? C25 C24 C23 110.33(14) . . ? O8 C24 H24 109.7 . . ? C25 C24 H24 109.7 . . ? C23 C24 H24 109.7 . . ? O7 C25 C26 105.88(13) . . ? O7 C25 C24 110.06(14) . . ? C26 C25 C24 110.45(14) . . ? O7 C25 H25 110.1 . . ? C26 C25 H25 110.1 . . ? C24 C25 H25 110.1 . . ? O6 C26 C25 105.85(14) . . ? O6 C26 C27 108.56(14) . . ? C25 C26 C27 111.93(14) . . ? O6 C26 H26 110.1 . . ? C25 C26 H26 110.1 . . ? C27 C26 H26 110.1 . . ? O13 C27 C28 108.60(14) . . ? O13 C27 C26 108.06(13) . . ? C28 C27 C26 113.32(14) . . ? O13 C27 H27 108.9 . . ? C28 C27 H27 108.9 . . ? C26 C27 H27 108.9 . . ? O5 C28 C27 109.47(14) . . ? O5 C28 H28A 109.8 . . ? C27 C28 H28A 109.8 . . ? O5 C28 H28B 109.8 . . ? C27 C28 H28B 109.8 . . ? H28A C28 H28B 108.2 . . ? O9 C29 O5 123.33(17) . . ? O9 C29 C30 124.80(18) . . ? O5 C29 C30 111.87(17) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O96 C31 O6 124.06(16) . . ? O96 C31 C32 126.05(17) . . ? O6 C31 C32 109.88(15) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O11 C33 O7 123.91(18) . . ? O11 C33 C34 124.78(19) . . ? O7 C33 C34 111.25(17) . . ? C33 C34 H34A 109.5 . . ? C33 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C33 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O10 C35 O8 122.2(2) . . ? O10 C35 C36 124.8(2) . . ? O8 C35 C36 113.0(2) . . ? C11 N1 C10 118.87(14) . . ? C11 N1 S 122.44(12) . . ? C10 N1 S 111.21(12) . . ? O4 N2 C12 107.59(13) . . ? O4 N2 H2 126.2 . . ? C12 N2 H2 126.2 . . ? C15 O4 N2 107.44(13) . . ? C29 O5 C28 116.05(14) . . ? C31 O6 C26 117.80(13) . . ? C33 O7 C25 118.94(14) . . ? C35 O8 C24 117.36(16) . . ? C27 O13 C23 111.78(13) . . ? O2 S O1 117.05(9) . . ? O2 S N1 109.14(8) . . ? O1 S N1 109.68(8) . . ? O2 S C1 110.46(9) . . ? O1 S C1 112.86(9) . . ? N1 S C1 95.48(8) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S C1 C2 C3 140.97(15) . . . . ? S C1 C2 C10 22.45(19) . . . . ? S C1 C2 C6 -95.62(17) . . . . ? C1 C2 C3 C4 170.60(17) . . . . ? C10 C2 C3 C4 -69.10(18) . . . . ? C6 C2 C3 C4 38.94(18) . . . . ? C2 C3 C4 C5 -3.8(2) . . . . ? C3 C4 C5 C9 74.3(2) . . . . ? C3 C4 C5 C6 -32.8(2) . . . . ? C4 C5 C6 C7 175.06(16) . . . . ? C9 C5 C6 C7 64.0(2) . . . . ? C4 C5 C6 C8 -61.6(2) . . . . ? C9 C5 C6 C8 -172.61(17) . . . . ? C4 C5 C6 C2 54.52(16) . . . . ? C9 C5 C6 C2 -56.51(17) . . . . ? C1 C2 C6 C7 53.1(2) . . . . ? C3 C2 C6 C7 -175.82(17) . . . . ? C10 C2 C6 C7 -67.1(2) . . . . ? C1 C2 C6 C8 -70.5(2) . . . . ? C3 C2 C6 C8 60.6(2) . . . . ? C10 C2 C6 C8 169.28(16) . . . . ? C1 C2 C6 C5 172.00(16) . . . . ? C3 C2 C6 C5 -56.91(16) . . . . ? C10 C2 C6 C5 51.76(16) . . . . ? C4 C5 C9 C10 -66.3(2) . . . . ? C6 C5 C9 C10 41.4(2) . . . . ? C5 C9 C10 N1 -122.24(17) . . . . ? C5 C9 C10 C2 -7.4(2) . . . . ? C1 C2 C10 N1 -35.0(2) . . . . ? C3 C2 C10 N1 -161.51(14) . . . . ? C6 C2 C10 N1 92.17(16) . . . . ? C1 C2 C10 C9 -156.01(16) . . . . ? C3 C2 C10 C9 77.46(18) . . . . ? C6 C2 C10 C9 -28.85(18) . . . . ? O3 C11 C12 N2 -26.2(2) . . . . ? N1 C11 C12 N2 163.17(14) . . . . ? O3 C11 C12 C13 93.89(19) . . . . ? N1 C11 C12 C13 -76.72(18) . . . . ? N2 C12 C13 C22 -61.25(19) . . . . ? C11 C12 C13 C22 176.88(14) . . . . ? N2 C12 C13 C14 61.90(18) . . . . ? C11 C12 C13 C14 -59.97(18) . . . . ? O4 C15 C16 C21 100.3(2) . . . . ? O4 C15 C16 C17 -78.5(2) . . . . ? C21 C16 C17 C18 -1.7(3) . . . . ? C15 C16 C17 C18 177.18(18) . . . . ? C16 C17 C18 C19 1.1(3) . . . . ? C17 C18 C19 C20 -0.4(3) . . . . ? C18 C19 C20 C21 0.2(4) . . . . ? C17 C16 C21 C20 1.5(3) . . . . ? C15 C16 C21 C20 -177.4(2) . . . . ? C19 C20 C21 C16 -0.8(4) . . . . ? C14 C13 C22 C23 165.56(14) . . . . ? C12 C13 C22 C23 -69.36(19) . . . . ? C13 C22 C23 O13 -55.95(19) . . . . ? C13 C22 C23 C24 -173.06(14) . . . . ? O13 C23 C24 O8 178.41(13) . . . . ? C22 C23 C24 O8 -64.03(18) . . . . ? O13 C23 C24 C25 59.90(17) . . . . ? C22 C23 C24 C25 177.45(14) . . . . ? O8 C24 C25 O7 72.07(17) . . . . ? C23 C24 C25 O7 -168.51(13) . . . . ? O8 C24 C25 C26 -171.37(13) . . . . ? C23 C24 C25 C26 -51.96(18) . . . . ? O7 C25 C26 O6 -73.34(15) . . . . ? C24 C25 C26 O6 167.54(13) . . . . ? O7 C25 C26 C27 168.56(13) . . . . ? C24 C25 C26 C27 49.44(19) . . . . ? O6 C26 C27 O13 -171.30(13) . . . . ? C25 C26 C27 O13 -54.82(18) . . . . ? O6 C26 C27 C28 68.31(18) . . . . ? C25 C26 C27 C28 -175.21(14) . . . . ? O13 C27 C28 O5 -63.90(17) . . . . ? C26 C27 C28 O5 56.19(19) . . . . ? O3 C11 N1 C10 -7.1(2) . . . . ? C12 C11 N1 C10 163.75(15) . . . . ? O3 C11 N1 S 140.09(15) . . . . ? C12 C11 N1 S -49.1(2) . . . . ? C9 C10 N1 C11 -62.5(2) . . . . ? C2 C10 N1 C11 -176.04(14) . . . . ? C9 C10 N1 S 146.91(14) . . . . ? C2 C10 N1 S 33.36(17) . . . . ? C11 C12 N2 O4 -76.77(17) . . . . ? C13 C12 N2 O4 164.43(13) . . . . ? C16 C15 O4 N2 -67.64(18) . . . . ? C12 N2 O4 C15 -110.80(15) . . . . ? O9 C29 O5 C28 -3.7(3) . . . . ? C30 C29 O5 C28 175.99(16) . . . . ? C27 C28 O5 C29 -151.24(15) . . . . ? O96 C31 O6 C26 -0.2(3) . . . . ? C32 C31 O6 C26 179.28(15) . . . . ? C25 C26 O6 C31 136.26(15) . . . . ? C27 C26 O6 C31 -103.42(16) . . . . ? O11 C33 O7 C25 4.9(3) . . . . ? C34 C33 O7 C25 -177.52(17) . . . . ? C26 C25 O7 C33 141.26(16) . . . . ? C24 C25 O7 C33 -99.36(18) . . . . ? O10 C35 O8 C24 -13.9(5) . . . . ? C36 C35 O8 C24 169.56(18) . . . . ? C25 C24 O8 C35 -107.1(2) . . . . ? C23 C24 O8 C35 132.9(2) . . . . ? C28 C27 O13 C23 -170.83(13) . . . . ? C26 C27 O13 C23 65.87(16) . . . . ? C22 C23 O13 C27 170.50(13) . . . . ? C24 C23 O13 C27 -68.59(16) . . . . ? C11 N1 S O2 -53.77(16) . . . . ? C10 N1 S O2 95.60(13) . . . . ? C11 N1 S O1 75.67(15) . . . . ? C10 N1 S O1 -134.95(12) . . . . ? C11 N1 S C1 -167.67(15) . . . . ? C10 N1 S C1 -18.29(13) . . . . ? C2 C1 S O2 -115.96(14) . . . . ? C2 C1 S O1 110.88(14) . . . . ? C2 C1 S N1 -3.18(15) . . . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.726 _refine_diff_density_min -0.455 _refine_diff_density_rms 0.072 loop_ _publcif_jmolscript.group _publcif_jmolscript.id _publcif_jmolscript.model _publcif_jmolscript.model_type _publcif_jmolscript.type _publcif_jmolscript.type_group _publcif_jmolscript.caption _publcif_jmolscript.script ? ? ? ? ? ? ? ? # Attachment 'RX528_25a_.cif' data_528GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 731618' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C18 H26 O11' _chemical_formula_sum 'C18 H26 O11' _chemical_melting_point ? _exptl_crystal_description plate _exptl_crystal_colour colorless _diffrn_ambient_temperature 100(1) _chemical_formula_weight 418.39 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_int_tables_number 19 _chemical_absolute_configuration ad loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.9034(12) _cell_length_b 10.2924(13) _cell_length_c 20.413(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2080.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 7468 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 33.41 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.120 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.980 _exptl_absorpt_correction_T_max 0.986 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'kappa X8 APEX II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22090 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_sigmaI/netI 0.0381 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 37.38 _reflns_number_total 9135 _reflns_number_gt 6941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0753P)^2^+0.1827P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(2) _refine_ls_number_reflns 9135 _refine_ls_number_parameters 268 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0737 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1193 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 0.90542(14) 0.41244(15) 0.18891(8) 0.0280(3) Uani 1 1 d . . . H1A H 0.9519 0.3800 0.1504 0.034 Uiso 1 1 calc R . . H1B H 0.9665 0.4054 0.2259 0.034 Uiso 1 1 calc R . . C2 C 0.78871(17) 0.25942(14) 0.25525(7) 0.0305(3) Uani 1 1 d . . . C3 C 0.66717(19) 0.17201(18) 0.25733(11) 0.0444(5) Uani 1 1 d . . . H3A H 0.6567 0.1376 0.3007 0.067 Uiso 1 1 calc R . . H3B H 0.6791 0.1019 0.2269 0.067 Uiso 1 1 calc R . . H3C H 0.5881 0.2208 0.2457 0.067 Uiso 1 1 calc R . . C4 C 0.86845(13) 0.55241(13) 0.17860(6) 0.0217(2) Uani 1 1 d . . . H4 H 0.9519 0.6031 0.1749 0.026 Uiso 1 1 calc R . . C5 C 0.78221(12) 0.61136(13) 0.23362(6) 0.0203(2) Uani 1 1 d . . . H5 H 0.6979 0.5624 0.2383 0.024 Uiso 1 1 calc R . . C6 C 0.75115(12) 0.75428(13) 0.22057(6) 0.0185(2) Uani 1 1 d . . . H6 H 0.8330 0.8069 0.2257 0.022 Uiso 1 1 calc R . . C7 C 0.68266(14) 0.85858(15) 0.32109(7) 0.0261(3) Uani 1 1 d . . . C8 C 0.56150(15) 0.89686(15) 0.36068(7) 0.0268(3) Uani 1 1 d . . . H8A H 0.4919 0.9280 0.3320 0.040 Uiso 1 1 calc R . . H8B H 0.5861 0.9643 0.3909 0.040 Uiso 1 1 calc R . . H8C H 0.5290 0.8228 0.3845 0.040 Uiso 1 1 calc R . . C9 C 0.80344(17) 0.54609(14) 0.34591(7) 0.0284(3) Uani 1 1 d . . . C10 C 0.9039(2) 0.5336(2) 0.40015(9) 0.0466(5) Uani 1 1 d . . . H10A H 0.9438 0.6169 0.4088 0.070 Uiso 1 1 calc R . . H10B H 0.9731 0.4732 0.3876 0.070 Uiso 1 1 calc R . . H10C H 0.8593 0.5028 0.4389 0.070 Uiso 1 1 calc R . . C11 C 0.78346(13) 0.69813(11) 0.10167(6) 0.0186(2) Uani 1 1 d . . . H11 H 0.8735 0.7376 0.1016 0.022 Uiso 1 1 calc R . . C12 C 0.69516(12) 0.76839(11) 0.15162(6) 0.0174(2) Uani 1 1 d . . . H12 H 0.6036 0.7324 0.1501 0.021 Uiso 1 1 calc R . . C13 C 0.72251(14) 0.71059(12) 0.03412(6) 0.0203(2) Uani 1 1 d . . . H13A H 0.6343 0.6697 0.0331 0.024 Uiso 1 1 calc R . . H13B H 0.7797 0.6677 0.0022 0.024 Uiso 1 1 calc R . . C14 C 0.70953(13) 0.85542(12) 0.01747(6) 0.0196(2) Uani 1 1 d . . . H14 H 0.8007 0.8924 0.0168 0.024 Uiso 1 1 calc R . . C15 C 0.62962(13) 0.92503(12) 0.07182(6) 0.0187(2) Uani 1 1 d . . . C16 C 0.64697(16) 0.87756(15) -0.04998(6) 0.0279(3) Uani 1 1 d . . . H16A H 0.6474 0.9688 -0.0599 0.042 Uiso 1 1 calc R . . H16B H 0.5557 0.8462 -0.0501 0.042 Uiso 1 1 calc R . . H16C H 0.6985 0.8317 -0.0824 0.042 Uiso 1 1 calc R . . C17 C 0.63531(15) 1.07297(13) 0.06116(6) 0.0234(2) Uani 1 1 d . . . C18 C 0.7740(2) 1.25295(16) 0.03867(9) 0.0406(4) Uani 1 1 d . . . H18A H 0.8679 1.2747 0.0346 0.061 Uiso 1 1 calc R . . H18B H 0.7337 1.3056 0.0722 0.061 Uiso 1 1 calc R . . H18C H 0.7292 1.2687 -0.0023 0.061 Uiso 1 1 calc R . . O1 O 0.78627(11) 0.33384(10) 0.20107(5) 0.0278(2) Uani 1 1 d . . . O2 O 0.87826(15) 0.26434(13) 0.29568(6) 0.0408(3) Uani 1 1 d . . . O3 O 0.86160(11) 0.60045(11) 0.29306(5) 0.0269(2) Uani 1 1 d . . . O4 O 0.64645(9) 0.79933(9) 0.26503(4) 0.02037(17) Uani 1 1 d . . . O5 O 0.79770(13) 0.87657(19) 0.33710(7) 0.0573(5) Uani 1 1 d . . . O6 O 0.68773(14) 0.51132(15) 0.34676(7) 0.0457(3) Uani 1 1 d . . . O7 O 0.79537(10) 0.56415(9) 0.11863(5) 0.02108(17) Uani 1 1 d . . . O8 O 0.69049(9) 0.90430(8) 0.13514(4) 0.01864(16) Uani 1 1 d . . . O9 O 0.49707(9) 0.88108(10) 0.07073(5) 0.02311(18) Uani 1 1 d . . . H9 H 0.4501 0.9286 0.0935 0.035 Uiso 1 1 calc R . . O10 O 0.53551(13) 1.13872(12) 0.05532(7) 0.0374(3) Uani 1 1 d . . . O11 O 0.76077(12) 1.11646(10) 0.05606(5) 0.0307(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0169(6) 0.0315(7) 0.0357(7) 0.0052(5) 0.0004(5) 0.0051(5) C2 0.0311(7) 0.0286(6) 0.0317(7) 0.0096(5) 0.0061(6) 0.0127(6) C3 0.0384(9) 0.0393(8) 0.0554(11) 0.0248(8) 0.0072(8) 0.0050(7) C4 0.0138(5) 0.0265(5) 0.0249(6) -0.0006(4) 0.0002(4) 0.0002(4) C5 0.0147(5) 0.0258(5) 0.0205(5) 0.0014(4) -0.0004(4) -0.0028(4) C6 0.0134(5) 0.0245(5) 0.0176(5) -0.0033(4) 0.0014(4) -0.0026(4) C7 0.0213(6) 0.0359(7) 0.0211(6) -0.0083(5) 0.0024(4) -0.0025(5) C8 0.0249(6) 0.0306(6) 0.0250(6) -0.0042(5) 0.0080(5) -0.0008(5) C9 0.0335(7) 0.0270(6) 0.0247(6) 0.0045(5) 0.0077(5) 0.0054(5) C10 0.0592(12) 0.0546(11) 0.0260(8) 0.0121(7) -0.0035(8) 0.0087(9) C11 0.0153(5) 0.0207(5) 0.0198(5) -0.0044(4) 0.0012(4) -0.0015(4) C12 0.0152(5) 0.0195(5) 0.0174(5) -0.0039(4) 0.0002(4) -0.0025(4) C13 0.0218(6) 0.0221(5) 0.0171(5) -0.0055(4) 0.0020(4) -0.0019(4) C14 0.0188(5) 0.0244(5) 0.0157(5) -0.0030(4) 0.0014(4) -0.0028(4) C15 0.0164(5) 0.0222(5) 0.0174(5) -0.0028(4) -0.0011(4) -0.0011(4) C16 0.0306(7) 0.0354(7) 0.0177(5) -0.0007(5) -0.0011(5) -0.0022(6) C17 0.0273(6) 0.0243(5) 0.0188(5) -0.0023(4) -0.0026(5) 0.0007(5) C18 0.0505(11) 0.0249(6) 0.0464(9) 0.0069(6) 0.0027(8) -0.0061(7) O1 0.0226(5) 0.0262(4) 0.0345(5) 0.0106(4) -0.0028(4) 0.0034(4) O2 0.0476(7) 0.0412(6) 0.0335(6) 0.0111(5) -0.0049(5) 0.0098(6) O3 0.0231(5) 0.0365(5) 0.0213(4) 0.0067(4) -0.0029(4) -0.0054(4) O4 0.0157(4) 0.0277(4) 0.0177(4) -0.0031(3) 0.0017(3) -0.0015(3) O5 0.0212(5) 0.1032(12) 0.0476(8) -0.0478(8) 0.0001(5) -0.0048(7) O6 0.0331(7) 0.0611(8) 0.0430(7) 0.0217(6) 0.0160(5) 0.0029(6) O7 0.0193(4) 0.0204(4) 0.0236(4) -0.0032(3) -0.0007(3) 0.0009(3) O8 0.0196(4) 0.0200(4) 0.0163(4) -0.0040(3) -0.0013(3) -0.0013(3) O9 0.0152(4) 0.0314(5) 0.0228(4) -0.0063(4) 0.0013(3) -0.0009(4) O10 0.0333(6) 0.0292(5) 0.0497(7) -0.0030(5) -0.0076(5) 0.0078(4) O11 0.0314(5) 0.0238(4) 0.0370(5) 0.0027(4) 0.0013(4) -0.0047(4) _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 O1 1.4520(18) . ? C1 C4 1.5013(19) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 O2 1.213(2) . ? C2 O1 1.3456(17) . ? C2 C3 1.503(3) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 O7 1.4272(16) . ? C4 C5 1.5359(18) . ? C4 H4 0.9800 . ? C5 O3 1.4502(15) . ? C5 C6 1.5262(19) . ? C5 H5 0.9800 . ? C6 O4 1.4540(15) . ? C6 C12 1.5197(17) . ? C6 H6 0.9800 . ? C7 O5 1.1996(19) . ? C7 O4 1.3454(16) . ? C7 C8 1.4994(19) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 O6 1.201(2) . ? C9 O3 1.3448(17) . ? C9 C10 1.494(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 O7 1.4266(15) . ? C11 C13 1.5107(18) . ? C11 C12 1.5255(16) . ? C11 H11 0.9800 . ? C12 O8 1.4395(14) . ? C12 H12 0.9800 . ? C13 C14 1.5342(17) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C16 1.5269(18) . ? C14 C15 1.5397(17) . ? C14 H14 0.9800 . ? C15 O9 1.3887(15) . ? C15 O8 1.4420(14) . ? C15 C17 1.5391(18) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 O10 1.2038(18) . ? C17 O11 1.3248(18) . ? C18 O11 1.4548(19) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? O9 H9 0.8200 . ? 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 C1 C4 111.12(11) . . ? O1 C1 H1A 109.4 . . ? C4 C1 H1A 109.4 . . ? O1 C1 H1B 109.4 . . ? C4 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? O2 C2 O1 123.29(15) . . ? O2 C2 C3 126.25(14) . . ? O1 C2 C3 110.46(14) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O7 C4 C1 108.97(11) . . ? O7 C4 C5 108.17(10) . . ? C1 C4 C5 114.34(11) . . ? O7 C4 H4 108.4 . . ? C1 C4 H4 108.4 . . ? C5 C4 H4 108.4 . . ? O3 C5 C6 109.27(10) . . ? O3 C5 C4 106.25(10) . . ? C6 C5 C4 111.41(10) . . ? O3 C5 H5 109.9 . . ? C6 C5 H5 109.9 . . ? C4 C5 H5 109.9 . . ? O4 C6 C12 106.71(10) . . ? O4 C6 C5 110.00(10) . . ? C12 C6 C5 109.10(10) . . ? O4 C6 H6 110.3 . . ? C12 C6 H6 110.3 . . ? C5 C6 H6 110.3 . . ? O5 C7 O4 123.70(13) . . ? O5 C7 C8 124.94(13) . . ? O4 C7 C8 111.36(12) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O6 C9 O3 122.98(15) . . ? O6 C9 C10 126.81(15) . . ? O3 C9 C10 110.19(15) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O7 C11 C13 109.67(9) . . ? O7 C11 C12 110.08(10) . . ? C13 C11 C12 109.92(10) . . ? O7 C11 H11 109.0 . . ? C13 C11 H11 109.0 . . ? C12 C11 H11 109.0 . . ? O8 C12 C6 108.72(9) . . ? O8 C12 C11 108.84(9) . . ? C6 C12 C11 111.38(10) . . ? O8 C12 H12 109.3 . . ? C6 C12 H12 109.3 . . ? C11 C12 H12 109.3 . . ? C11 C13 C14 108.55(9) . . ? C11 C13 H13A 110.0 . . ? C14 C13 H13A 110.0 . . ? C11 C13 H13B 110.0 . . ? C14 C13 H13B 110.0 . . ? H13A C13 H13B 108.4 . . ? C16 C14 C13 112.26(10) . . ? C16 C14 C15 111.83(11) . . ? C13 C14 C15 109.61(10) . . ? C16 C14 H14 107.6 . . ? C13 C14 H14 107.6 . . ? C15 C14 H14 107.6 . . ? O9 C15 O8 111.19(10) . . ? O9 C15 C17 110.77(11) . . ? O8 C15 C17 104.94(9) . . ? O9 C15 C14 108.82(10) . . ? O8 C15 C14 111.23(10) . . ? C17 C15 C14 109.85(10) . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O10 C17 O11 124.91(13) . . ? O10 C17 C15 122.70(13) . . ? O11 C17 C15 112.32(11) . . ? O11 C18 H18A 109.5 . . ? O11 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O11 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C2 O1 C1 116.30(12) . . ? C9 O3 C5 118.11(11) . . ? C7 O4 C6 119.04(10) . . ? C11 O7 C4 109.38(9) . . ? C12 O8 C15 111.51(9) . . ? C15 O9 H9 109.5 . . ? C17 O11 C18 115.48(13) . . ? 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 O1 C1 C4 O7 -67.65(15) . . . . ? O1 C1 C4 C5 53.51(16) . . . . ? O7 C4 C5 O3 -178.53(9) . . . . ? C1 C4 C5 O3 59.86(14) . . . . ? O7 C4 C5 C6 -59.62(13) . . . . ? C1 C4 C5 C6 178.78(11) . . . . ? O3 C5 C6 O4 -75.38(12) . . . . ? C4 C5 C6 O4 167.52(10) . . . . ? O3 C5 C6 C12 167.88(9) . . . . ? C4 C5 C6 C12 50.79(13) . . . . ? O4 C6 C12 O8 72.07(11) . . . . ? C5 C6 C12 O8 -169.12(9) . . . . ? O4 C6 C12 C11 -168.00(9) . . . . ? C5 C6 C12 C11 -49.20(12) . . . . ? O7 C11 C12 O8 177.16(9) . . . . ? C13 C11 C12 O8 -61.93(12) . . . . ? O7 C11 C12 C6 57.30(13) . . . . ? C13 C11 C12 C6 178.22(10) . . . . ? O7 C11 C13 C14 179.42(10) . . . . ? C12 C11 C13 C14 58.25(13) . . . . ? C11 C13 C14 C16 -179.33(11) . . . . ? C11 C13 C14 C15 -54.42(13) . . . . ? C16 C14 C15 O9 57.71(14) . . . . ? C13 C14 C15 O9 -67.45(13) . . . . ? C16 C14 C15 O8 -179.47(10) . . . . ? C13 C14 C15 O8 55.38(13) . . . . ? C16 C14 C15 C17 -63.72(13) . . . . ? C13 C14 C15 C17 171.13(10) . . . . ? O9 C15 C17 O10 2.55(18) . . . . ? O8 C15 C17 O10 -117.53(14) . . . . ? C14 C15 C17 O10 122.80(14) . . . . ? O9 C15 C17 O11 -174.34(10) . . . . ? O8 C15 C17 O11 65.58(13) . . . . ? C14 C15 C17 O11 -54.09(14) . . . . ? O2 C2 O1 C1 6.6(2) . . . . ? C3 C2 O1 C1 -173.19(13) . . . . ? C4 C1 O1 C2 -127.25(13) . . . . ? O6 C9 O3 C5 -3.1(2) . . . . ? C10 C9 O3 C5 175.38(13) . . . . ? C6 C5 O3 C9 111.06(13) . . . . ? C4 C5 O3 C9 -128.63(12) . . . . ? O5 C7 O4 C6 -0.2(2) . . . . ? C8 C7 O4 C6 -179.47(11) . . . . ? C12 C6 O4 C7 -146.99(12) . . . . ? C5 C6 O4 C7 94.79(13) . . . . ? C13 C11 O7 C4 172.66(10) . . . . ? C12 C11 O7 C4 -66.27(12) . . . . ? C1 C4 O7 C11 -168.39(11) . . . . ? C5 C4 O7 C11 66.75(12) . . . . ? C6 C12 O8 C15 -176.09(9) . . . . ? C11 C12 O8 C15 62.42(12) . . . . ? O9 C15 O8 C12 61.42(12) . . . . ? C17 C15 O8 C12 -178.77(10) . . . . ? C14 C15 O8 C12 -60.03(12) . . . . ? O10 C17 O11 C18 -3.4(2) . . . . ? C15 C17 O11 C18 173.44(12) . . . . ? _diffrn_measured_fraction_theta_max 0.870 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.535 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.060