# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _publ_contact_author ; Martin Nieger Laboratory of Inorganic Chemistry Department of Chemistry Universitity of Helsinki P.O. Box 55 FIN-00014 University of Helsinki Finland ; _publ_contact_author_phone '++358 9 191 50221' _publ_contact_author_fax '++358 9 191 50198' _publ_contact_author_email martin.nieger@helsinki.fi _publ_requested_coeditor_name ? _publ_contact_letter ; enclosed you will find the necessary data for our publication in Org. Biomol. Chem. ; #============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; Thiolation of Symmetrical and Unsymmetrical Diketopiperazines ; loop_ _publ_author_name _publ_author_address B.M.Ruff ; Institute of Organic Chemistry Karlsruhe Institute of Technology (KIT) Fritz-Haber-Weg 6 D-76131 Karlsruhe Germany ; S.Zhong ; Institute of Organic Chemistry Karlsruhe Institute of Technology (KIT) Fritz-Haber-Weg 6 D-76131 Karlsruhe Germany ; M.Nieger ; Laboratory of Inorganic Chemistry Department of Chemistry Universitity of Helsinki P.O. Box 55 FIN-00014 University of Helsinki Finland ; S.Brase ; Institute of Organic Chemistry Karlsruhe Institute of Technology (KIT) Fritz-Haber-Weg 6 D-76131 Karlsruhe Germany ; _publ_contact_author_name 'Martin Nieger' # Attachment '- crystal structures.cif' # 1. SUBMISSION DETAILS #=========================================================================== data_sb108_hy _database_code_depnum_ccdc_archive 'CCDC 846901' #TrackingRef '- crystal structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; (rac)-10a,10'a-bis(methylthio)octahydro-1H,1'H-5a,5'a-bidipyrrolo- [1,2-a:1',2'-d]pyrazine-5,5',10,10'(6H,6'H,10aH,10'aH)-tetraone ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H30 N4 O4 S2, 0.125(H2 O)' _chemical_formula_sum 'C22 H30.25 N4 O4.125 S2' _chemical_formula_weight 480.88 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 triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.648(1) _cell_length_b 14.822(2) _cell_length_c 16.441(3) _cell_angle_alpha 104.68(1) _cell_angle_beta 103.17(1) _cell_angle_gamma 91.75(1) _cell_volume 2204.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 51 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1021 _exptl_absorpt_coefficient_mu 0.281 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 480 sec./deg., 2 deg., 4 sets, 152 frames, ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15993 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0840 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.03 _reflns_number_total 7743 _reflns_number_gt 5119 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius, 1998)' _computing_cell_refinement 'EVALCCD (Duisenberg et al., 2003)' _computing_data_reduction 'EVALCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0519P)^2^+3.2612P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7743 _refine_ls_number_parameters 591 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.1058 _refine_ls_R_factor_gt 0.0583 _refine_ls_wR_factor_ref 0.1458 _refine_ls_wR_factor_gt 0.1246 _refine_ls_goodness_of_fit_ref 1.012 _refine_ls_restrained_S_all 1.012 _refine_ls_shift/su_max 0.000 _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 0.9027(4) 0.6532(3) 1.0131(2) 0.0242(8) Uani 1 1 d . . . H1A H 1.0057 0.6710 1.0211 0.029 Uiso 1 1 calc R . . H1B H 0.8854 0.6514 1.0698 0.029 Uiso 1 1 calc R . . C2 C 0.8564(4) 0.5584(3) 0.9470(3) 0.0314(9) Uani 1 1 d . . . H2A H 0.9265 0.5425 0.9111 0.038 Uiso 1 1 calc R . . H2B H 0.8487 0.5086 0.9765 0.038 Uiso 1 1 calc R . . C3 C 0.7118(4) 0.5676(2) 0.8910(2) 0.0229(8) Uani 1 1 d . . . H3A H 0.6965 0.5261 0.8315 0.027 Uiso 1 1 calc R . . H3B H 0.6332 0.5529 0.9165 0.027 Uiso 1 1 calc R . . N4 N 0.7229(3) 0.6674(2) 0.89135(18) 0.0184(6) Uani 1 1 d . . . C5 C 0.6960(3) 0.6899(3) 0.8145(2) 0.0203(8) Uani 1 1 d . . . O5 O 0.6083(2) 0.64268(17) 0.75032(15) 0.0244(6) Uani 1 1 d . . . C5A C 0.7919(3) 0.7682(3) 0.8071(2) 0.0207(8) Uani 1 1 d . . . S5 S 0.92139(10) 0.70279(7) 0.74980(6) 0.0308(3) Uani 1 1 d . . . C5B C 0.8188(5) 0.6628(3) 0.6391(3) 0.0449(12) Uani 1 1 d . . . H5B1 H 0.7270 0.6311 0.6371 0.067 Uiso 1 1 calc R . . H5B2 H 0.8717 0.6189 0.6051 0.067 Uiso 1 1 calc R . . H5B3 H 0.8019 0.7165 0.6147 0.067 Uiso 1 1 calc R . . C6 C 0.7264(4) 0.8418(3) 0.7646(2) 0.0256(8) Uani 1 1 d . . . H6A H 0.6445 0.8659 0.7877 0.031 Uiso 1 1 calc R . . H6B H 0.6941 0.8165 0.7009 0.031 Uiso 1 1 calc R . . C7 C 0.8512(4) 0.9182(3) 0.7898(2) 0.0293(9) Uani 1 1 d . . . H7A H 0.9092 0.9067 0.7463 0.035 Uiso 1 1 calc R . . H7B H 0.8155 0.9808 0.7943 0.035 Uiso 1 1 calc R . . C8 C 0.9399(4) 0.9123(3) 0.8781(2) 0.0258(8) Uani 1 1 d . . . H8A H 1.0424 0.9096 0.8781 0.031 Uiso 1 1 calc R . . H8B H 0.9298 0.9669 0.9249 0.031 Uiso 1 1 calc R . . N9 N 0.8795(3) 0.8244(2) 0.88901(18) 0.0204(7) Uani 1 1 d . . . C10 C 0.9018(3) 0.8060(2) 0.9670(2) 0.0193(8) Uani 1 1 d . . . O10 O 0.9878(2) 0.85536(17) 1.03055(15) 0.0219(6) Uani 1 1 d . . . C10A C 0.8100(3) 0.7241(2) 0.9751(2) 0.0180(7) Uani 1 1 d . . . C11 C 0.7813(4) 0.8239(3) 1.1271(2) 0.0241(8) Uani 1 1 d . . . H11A H 0.7396 0.8026 1.1695 0.029 Uiso 1 1 calc R . . H11B H 0.8842 0.8139 1.1384 0.029 Uiso 1 1 calc R . . C12 C 0.7612(4) 0.9278(3) 1.1341(2) 0.0296(9) Uani 1 1 d . . . H12A H 0.6941 0.9498 1.1707 0.035 Uiso 1 1 calc R . . H12B H 0.8539 0.9663 1.1603 0.035 Uiso 1 1 calc R . . C13 C 0.7010(4) 0.9360(3) 1.0420(2) 0.0228(8) Uani 1 1 d . . . H13A H 0.6317 0.9839 1.0412 0.027 Uiso 1 1 calc R . . H13B H 0.7782 0.9518 1.0158 0.027 Uiso 1 1 calc R . . N14 N 0.6305(3) 0.8414(2) 0.99702(18) 0.0186(6) Uani 1 1 d . . . C15 C 0.5092(3) 0.8265(3) 0.9332(2) 0.0212(8) Uani 1 1 d . . . O15 O 0.4747(2) 0.88156(18) 0.88924(16) 0.0270(6) Uani 1 1 d . . . C15A C 0.4048(3) 0.7455(3) 0.9292(2) 0.0235(8) Uani 1 1 d . . . S15 S 0.25238(9) 0.79948(7) 0.96750(6) 0.0282(2) Uani 1 1 d . . . C15B C 0.3350(4) 0.8663(3) 1.0763(2) 0.0289(9) Uani 1 1 d . . . H15A H 0.4046 0.8298 1.1041 0.043 Uiso 1 1 calc R . . H15B H 0.2617 0.8808 1.1090 0.043 Uiso 1 1 calc R . . H15C H 0.3838 0.9247 1.0750 0.043 Uiso 1 1 calc R . . C16 C 0.3355(4) 0.6758(3) 0.8427(3) 0.0339(10) Uani 1 1 d . . . H16A H 0.4062 0.6577 0.8077 0.041 Uiso 1 1 calc R . . H16B H 0.2561 0.7021 0.8091 0.041 Uiso 1 1 calc R . . C17 C 0.2799(4) 0.5914(3) 0.8687(3) 0.0424(11) Uani 1 1 d . . . H17A H 0.1765 0.5929 0.8663 0.051 Uiso 1 1 calc R . . H17B H 0.2945 0.5320 0.8290 0.051 Uiso 1 1 calc R . . C18 C 0.3649(4) 0.5993(3) 0.9611(3) 0.0359(10) Uani 1 1 d . . . H18A H 0.3012 0.6066 1.0014 0.043 Uiso 1 1 calc R . . H18B H 0.4173 0.5434 0.9639 0.043 Uiso 1 1 calc R . . N19 N 0.4652(3) 0.6841(2) 0.9825(2) 0.0247(7) Uani 1 1 d . . . C20 C 0.5975(3) 0.6905(3) 1.0332(2) 0.0208(8) Uani 1 1 d . . . O20 O 0.6356(3) 0.63436(18) 1.07591(16) 0.0275(6) Uani 1 1 d . . . C20A C 0.7030(3) 0.7697(2) 1.0335(2) 0.0171(7) Uani 1 1 d . . . C21 C 0.9274(5) 0.1217(3) 0.6731(3) 0.0451(12) Uani 1 1 d . . . H21A H 1.0263 0.1451 0.6766 0.054 Uiso 1 1 calc R . . H21B H 0.9247 0.1079 0.7286 0.054 Uiso 1 1 calc R . . C22 C 0.8787(6) 0.0336(4) 0.5978(3) 0.0581(15) Uani 1 1 d . . . H22A H 0.9586 0.0142 0.5707 0.070 Uiso 1 1 calc R . . H22B H 0.8461 -0.0184 0.6187 0.070 Uiso 1 1 calc R . . C23 C 0.7561(4) 0.0576(3) 0.5322(3) 0.0340(10) Uani 1 1 d . . . H23A H 0.7897 0.0714 0.4837 0.041 Uiso 1 1 calc R . . H23B H 0.6788 0.0057 0.5087 0.041 Uiso 1 1 calc R . . N24 N 0.7072(3) 0.1415(2) 0.58390(19) 0.0274(7) Uani 1 1 d . . . C25 C 0.5676(4) 0.1576(3) 0.5688(2) 0.0279(9) Uani 1 1 d . . . O25 O 0.4832(3) 0.1231(2) 0.49881(17) 0.0347(7) Uani 1 1 d . . . C25A C 0.5150(4) 0.2088(3) 0.6475(2) 0.0263(9) Uani 1 1 d . . . S25 S 0.40877(11) 0.11772(8) 0.67444(7) 0.0364(3) Uani 1 1 d . . . C25B C 0.5425(5) 0.0394(3) 0.6968(3) 0.0463(12) Uani 1 1 d . . . H25A H 0.5505 -0.0035 0.6422 0.069 Uiso 1 1 calc R . . H25B H 0.5149 0.0032 0.7339 0.069 Uiso 1 1 calc R . . H25C H 0.6347 0.0757 0.7265 0.069 Uiso 1 1 calc R . . C26 C 0.4160(4) 0.2859(3) 0.6370(2) 0.0310(9) Uani 1 1 d . . . H26A H 0.3149 0.2595 0.6146 0.037 Uiso 1 1 calc R . . H26B H 0.4411 0.3197 0.5968 0.037 Uiso 1 1 calc R . . C27 C 0.4409(4) 0.3515(3) 0.7292(3) 0.0411(11) Uani 1 1 d . . . H27A H 0.4658 0.4168 0.7291 0.049 Uiso 1 1 calc R . . H27B H 0.3535 0.3496 0.7509 0.049 Uiso 1 1 calc R . . C28 C 0.5629(4) 0.3173(3) 0.7859(2) 0.0210(8) Uani 1 1 d . . . H28A H 0.6329 0.3701 0.8233 0.025 Uiso 1 1 calc R . . H28B H 0.5274 0.2834 0.8229 0.025 Uiso 1 1 calc R . . N29 N 0.6277(3) 0.2531(2) 0.72204(19) 0.0269(7) Uani 1 1 d . . . C30 C 0.7693(4) 0.2429(3) 0.7344(2) 0.0304(9) Uani 1 1 d . . . O30 O 0.8529(3) 0.2757(2) 0.80510(17) 0.0473(8) Uani 1 1 d . . . C30A C 0.8224(4) 0.1960(3) 0.6552(2) 0.0298(9) Uani 1 1 d . . . C31 C 1.0203(4) 0.3370(4) 0.6942(3) 0.0553(14) Uani 1 1 d . . . H31A H 1.0441 0.3105 0.7447 0.066 Uiso 1 1 calc R . . H31B H 1.1055 0.3385 0.6704 0.066 Uiso 1 1 calc R . . C32 C 0.9736(6) 0.4346(4) 0.7206(4) 0.0730(18) Uani 1 1 d . . . H32A H 1.0180 0.4771 0.6940 0.088 Uiso 1 1 calc R . . H32B H 1.0025 0.4600 0.7844 0.088 Uiso 1 1 calc R . . C33 C 0.8120(5) 0.4260(3) 0.6888(3) 0.0544(14) Uani 1 1 d . . . H33A H 0.7649 0.4146 0.7332 0.065 Uiso 1 1 calc R . . H33B H 0.7786 0.4831 0.6727 0.065 Uiso 1 1 calc R . . N34 N 0.7850(3) 0.3453(2) 0.6130(2) 0.0350(8) Uani 1 1 d . . . C35 C 0.6970(4) 0.3495(3) 0.5370(3) 0.0371(10) Uani 1 1 d . . . O35 O 0.5938(3) 0.3956(2) 0.5335(3) 0.0600(10) Uani 1 1 d . . . C35A C 0.7417(4) 0.3032(3) 0.4548(3) 0.0351(10) Uani 1 1 d . . . S35 S 0.83728(11) 0.40390(8) 0.43390(8) 0.0432(3) Uani 1 1 d . . . C35B C 0.6991(5) 0.4780(3) 0.4054(3) 0.0494(12) Uani 1 1 d . . . H35A H 0.6276 0.4428 0.3535 0.074 Uiso 1 1 calc R . . H35B H 0.7417 0.5329 0.3938 0.074 Uiso 1 1 calc R . . H35C H 0.6531 0.4986 0.4535 0.074 Uiso 1 1 calc R . . C36 C 0.6300(5) 0.2464(4) 0.3781(3) 0.0526(14) Uani 1 1 d . . . H36A H 0.5623 0.2090 0.3967 0.063 Uiso 1 1 calc R . . H36B H 0.5758 0.2874 0.3459 0.063 Uiso 1 1 calc R . . C37 C 0.7109(6) 0.1844(4) 0.3238(3) 0.0626(15) Uani 1 1 d . . . H37A H 0.7197 0.2091 0.2744 0.075 Uiso 1 1 calc R . . H37B H 0.6605 0.1207 0.3005 0.075 Uiso 1 1 calc R . . C38 C 0.8607(5) 0.1811(3) 0.3811(3) 0.0457(12) Uani 1 1 d . . . H38A H 0.8787 0.1163 0.3833 0.055 Uiso 1 1 calc R . . H38B H 0.9367 0.2076 0.3600 0.055 Uiso 1 1 calc R . . N39 N 0.8517(3) 0.2401(2) 0.4667(2) 0.0297(8) Uani 1 1 d . . . C40 C 0.9362(4) 0.2335(3) 0.5412(2) 0.0299(9) Uani 1 1 d . . . O40 O 1.0402(3) 0.1860(2) 0.54328(18) 0.0438(8) Uani 1 1 d . . . C40A C 0.8917(4) 0.2774(3) 0.6239(2) 0.0317(9) Uani 1 1 d . . . O1W O 0.2169(13) 0.1657(9) 0.4292(8) 0.045(3) Uiso 0.25 1 d PD . . H1W1 H 0.303(5) 0.167(14) 0.454(8) 0.067 Uiso 0.25 1 d PD . . H1W2 H 0.164(12) 0.178(14) 0.464(7) 0.067 Uiso 0.25 1 d PD . . 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 0.0192(17) 0.025(2) 0.031(2) 0.0137(18) 0.0037(16) 0.0056(15) C2 0.030(2) 0.020(2) 0.044(2) 0.0100(19) 0.0070(18) 0.0058(16) C3 0.0265(18) 0.012(2) 0.029(2) 0.0035(16) 0.0075(16) 0.0004(15) N4 0.0180(14) 0.0130(17) 0.0218(15) 0.0026(13) 0.0024(12) -0.0016(12) C5 0.0183(17) 0.017(2) 0.0234(19) 0.0033(16) 0.0036(15) 0.0043(14) O5 0.0226(12) 0.0242(16) 0.0212(13) 0.0014(12) 0.0006(11) -0.0022(11) C5A 0.0190(17) 0.023(2) 0.0172(17) 0.0014(16) 0.0026(14) 0.0011(15) S5 0.0243(5) 0.0329(6) 0.0336(5) 0.0024(5) 0.0112(4) 0.0014(4) C5B 0.043(2) 0.051(3) 0.032(2) -0.009(2) 0.015(2) -0.005(2) C6 0.0251(18) 0.027(2) 0.0237(19) 0.0088(17) 0.0016(16) 0.0001(16) C7 0.034(2) 0.027(2) 0.029(2) 0.0107(18) 0.0081(17) -0.0004(17) C8 0.0280(19) 0.018(2) 0.032(2) 0.0103(17) 0.0061(17) -0.0055(15) N9 0.0195(14) 0.0175(17) 0.0230(16) 0.0052(13) 0.0033(12) -0.0022(12) C10 0.0132(16) 0.018(2) 0.029(2) 0.0062(17) 0.0077(15) 0.0058(14) O10 0.0145(11) 0.0254(15) 0.0213(13) 0.0020(12) 0.0003(10) -0.0021(10) C10A 0.0138(16) 0.018(2) 0.0189(17) 0.0026(15) 0.0011(14) -0.0001(14) C11 0.0236(18) 0.025(2) 0.0196(19) 0.0003(16) 0.0047(15) -0.0024(15) C12 0.032(2) 0.023(2) 0.029(2) -0.0001(18) 0.0069(17) -0.0046(17) C13 0.0224(17) 0.014(2) 0.030(2) 0.0028(16) 0.0060(16) -0.0010(14) N14 0.0173(14) 0.0116(16) 0.0238(15) 0.0027(13) 0.0013(12) 0.0007(11) C15 0.0166(17) 0.023(2) 0.0242(19) 0.0032(17) 0.0078(15) 0.0053(15) O15 0.0281(13) 0.0260(16) 0.0272(14) 0.0095(13) 0.0039(11) 0.0070(11) C15A 0.0164(16) 0.023(2) 0.028(2) 0.0028(17) 0.0034(15) 0.0049(15) S15 0.0164(4) 0.0324(6) 0.0318(5) 0.0022(5) 0.0046(4) 0.0040(4) C15B 0.0270(19) 0.031(2) 0.029(2) 0.0076(18) 0.0056(17) 0.0056(17) C16 0.0179(18) 0.038(3) 0.037(2) -0.002(2) 0.0042(17) -0.0003(17) C17 0.025(2) 0.030(3) 0.059(3) -0.005(2) 0.004(2) -0.0063(18) C18 0.0228(19) 0.026(2) 0.057(3) 0.009(2) 0.0069(19) -0.0044(17) N19 0.0155(14) 0.0199(18) 0.0373(18) 0.0057(15) 0.0064(13) -0.0013(12) C20 0.0211(18) 0.018(2) 0.0226(19) 0.0018(16) 0.0085(15) 0.0021(15) O20 0.0323(14) 0.0216(16) 0.0325(15) 0.0129(13) 0.0092(12) 0.0023(11) C20A 0.0167(16) 0.016(2) 0.0177(17) 0.0042(15) 0.0025(14) 0.0007(14) C21 0.046(3) 0.059(3) 0.036(2) 0.023(2) 0.009(2) 0.025(2) C22 0.082(4) 0.051(4) 0.040(3) 0.008(3) 0.013(3) 0.040(3) C23 0.042(2) 0.026(2) 0.033(2) 0.0033(19) 0.0121(19) 0.0067(18) N24 0.0308(17) 0.0235(19) 0.0224(16) 0.0007(14) 0.0017(14) 0.0037(14) C25 0.033(2) 0.020(2) 0.026(2) -0.0003(17) 0.0068(18) -0.0050(17) O25 0.0350(15) 0.0341(18) 0.0265(15) -0.0001(13) 0.0011(12) -0.0084(13) C25A 0.0260(19) 0.027(2) 0.026(2) 0.0074(18) 0.0058(16) 0.0006(16) S25 0.0449(6) 0.0303(6) 0.0338(6) 0.0052(5) 0.0145(5) -0.0075(5) C25B 0.072(3) 0.036(3) 0.036(2) 0.015(2) 0.017(2) 0.009(2) C26 0.0271(19) 0.036(3) 0.029(2) 0.0076(19) 0.0063(17) 0.0020(17) C27 0.044(2) 0.037(3) 0.039(2) 0.006(2) 0.007(2) 0.008(2) C28 0.0302(19) 0.014(2) 0.0153(17) 0.0001(15) 0.0030(15) 0.0015(15) N29 0.0301(17) 0.027(2) 0.0212(16) 0.0025(14) 0.0070(14) 0.0011(14) C30 0.029(2) 0.036(3) 0.022(2) 0.0068(18) -0.0002(17) 0.0019(18) O30 0.0397(16) 0.070(2) 0.0221(15) 0.0019(15) -0.0015(13) 0.0080(15) C30A 0.0229(18) 0.040(3) 0.024(2) 0.0083(19) -0.0013(16) 0.0056(17) C31 0.031(2) 0.078(4) 0.040(3) -0.009(3) 0.004(2) -0.016(2) C32 0.069(3) 0.062(4) 0.063(3) -0.031(3) 0.025(3) -0.033(3) C33 0.068(3) 0.027(3) 0.067(3) -0.010(2) 0.040(3) -0.012(2) N34 0.0387(19) 0.023(2) 0.042(2) 0.0018(17) 0.0147(17) 0.0025(15) C35 0.028(2) 0.034(3) 0.058(3) 0.022(2) 0.017(2) 0.0051(19) O35 0.0434(18) 0.058(2) 0.108(3) 0.053(2) 0.0407(19) 0.0283(17) C35A 0.032(2) 0.036(3) 0.044(2) 0.022(2) 0.0106(19) 0.0060(18) S35 0.0371(6) 0.0395(7) 0.0601(7) 0.0233(6) 0.0154(5) -0.0006(5) C35B 0.051(3) 0.042(3) 0.061(3) 0.029(3) 0.009(2) 0.006(2) C36 0.039(2) 0.061(4) 0.054(3) 0.033(3) -0.012(2) -0.018(2) C37 0.085(4) 0.055(4) 0.025(2) 0.003(2) -0.023(2) -0.004(3) C38 0.061(3) 0.047(3) 0.032(2) 0.011(2) 0.016(2) -0.002(2) N39 0.0287(17) 0.034(2) 0.0263(17) 0.0089(15) 0.0055(14) 0.0041(14) C40 0.0185(18) 0.036(3) 0.029(2) 0.0029(19) 0.0004(16) 0.0008(17) O40 0.0307(15) 0.061(2) 0.0418(17) 0.0140(16) 0.0099(13) 0.0183(15) C40A 0.0190(18) 0.044(3) 0.028(2) 0.0060(19) 0.0004(16) 0.0020(17) _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 1.525(5) . ? C1 C10A 1.560(5) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.517(5) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 N4 1.478(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? N4 C5 1.357(4) . ? N4 C10A 1.467(4) . ? C5 O5 1.226(4) . ? C5 C5A 1.510(5) . ? C5A N9 1.447(4) . ? C5A C6 1.517(5) . ? C5A S5 1.880(3) . ? S5 C5B 1.800(4) . ? C5B H5B1 0.9800 . ? C5B H5B2 0.9800 . ? C5B H5B3 0.9800 . ? C6 C7 1.536(5) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.532(5) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N9 1.480(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? N9 C10 1.350(4) . ? C10 O10 1.223(4) . ? C10 C10A 1.531(5) . ? C10A C20A 1.615(4) . ? C11 C12 1.537(5) . ? C11 C20A 1.546(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C13 1.530(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 N14 1.471(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? N14 C15 1.351(4) . ? N14 C20A 1.469(4) . ? C15 O15 1.227(4) . ? C15 C15A 1.522(5) . ? C15A N19 1.463(5) . ? C15A C16 1.522(5) . ? C15A S15 1.854(3) . ? S15 C15B 1.794(4) . ? C15B H15A 0.9800 . ? C15B H15B 0.9800 . ? C15B H15C 0.9800 . ? C16 C17 1.539(6) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.527(6) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 N19 1.478(5) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? N19 C20 1.342(4) . ? C20 O20 1.232(4) . ? C20 C20A 1.529(5) . ? C21 C22 1.529(7) . ? C21 C30A 1.556(6) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.525(6) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 N24 1.475(5) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? N24 C25 1.352(5) . ? N24 C30A 1.460(5) . ? C25 O25 1.224(4) . ? C25 C25A 1.527(5) . ? C25A N29 1.434(5) . ? C25A C26 1.530(5) . ? C25A S25 1.869(4) . ? S25 C25B 1.800(5) . ? C25B H25A 0.9800 . ? C25B H25B 0.9800 . ? C25B H25C 0.9800 . ? C26 C27 1.540(6) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 C28 1.513(5) . ? C27 H27A 0.9900 . ? C27 H27B 0.9900 . ? C28 N29 1.493(4) . ? C28 H28A 0.9900 . ? C28 H28B 0.9900 . ? N29 C30 1.353(5) . ? C30 O30 1.225(4) . ? C30 C30A 1.521(5) . ? C30A C40A 1.608(6) . ? C31 C32 1.514(8) . ? C31 C40A 1.555(5) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C32 C33 1.517(7) . ? C32 H32A 0.9900 . ? C32 H32B 0.9900 . ? C33 N34 1.459(5) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? N34 C35 1.359(5) . ? N34 C40A 1.475(5) . ? C35 O35 1.223(5) . ? C35 C35A 1.515(6) . ? C35A N39 1.449(5) . ? C35A C36 1.499(6) . ? C35A S35 1.876(4) . ? S35 C35B 1.809(5) . ? C35B H35A 0.9800 . ? C35B H35B 0.9800 . ? C35B H35C 0.9800 . ? C36 C37 1.482(7) . ? C36 H36A 0.9900 . ? C36 H36B 0.9900 . ? C37 C38 1.545(7) . ? C37 H37A 0.9900 . ? C37 H37B 0.9900 . ? C38 N39 1.478(5) . ? C38 H38A 0.9900 . ? C38 H38B 0.9900 . ? N39 C40 1.337(5) . ? C40 O40 1.242(4) . ? C40 C40A 1.513(5) . ? O1W H1W1 0.840(10) . ? O1W H1W2 0.840(10) . ? 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 C10A 105.6(3) . . ? C2 C1 H1A 110.6 . . ? C10A C1 H1A 110.6 . . ? C2 C1 H1B 110.6 . . ? C10A C1 H1B 110.6 . . ? H1A C1 H1B 108.7 . . ? C3 C2 C1 106.2(3) . . ? C3 C2 H2A 110.5 . . ? C1 C2 H2A 110.5 . . ? C3 C2 H2B 110.5 . . ? C1 C2 H2B 110.5 . . ? H2A C2 H2B 108.7 . . ? N4 C3 C2 102.4(3) . . ? N4 C3 H3A 111.3 . . ? C2 C3 H3A 111.3 . . ? N4 C3 H3B 111.3 . . ? C2 C3 H3B 111.3 . . ? H3A C3 H3B 109.2 . . ? C5 N4 C10A 127.1(3) . . ? C5 N4 C3 119.0(3) . . ? C10A N4 C3 110.2(3) . . ? O5 C5 N4 122.0(3) . . ? O5 C5 C5A 120.1(3) . . ? N4 C5 C5A 117.4(3) . . ? N9 C5A C5 114.3(3) . . ? N9 C5A C6 102.5(3) . . ? C5 C5A C6 119.5(3) . . ? N9 C5A S5 104.9(2) . . ? C5 C5A S5 102.4(2) . . ? C6 C5A S5 112.7(2) . . ? C5B S5 C5A 103.02(18) . . ? S5 C5B H5B1 109.5 . . ? S5 C5B H5B2 109.5 . . ? H5B1 C5B H5B2 109.5 . . ? S5 C5B H5B3 109.5 . . ? H5B1 C5B H5B3 109.5 . . ? H5B2 C5B H5B3 109.5 . . ? C5A C6 C7 102.5(3) . . ? C5A C6 H6A 111.3 . . ? C7 C6 H6A 111.3 . . ? C5A C6 H6B 111.3 . . ? C7 C6 H6B 111.3 . . ? H6A C6 H6B 109.2 . . ? C8 C7 C6 105.3(3) . . ? C8 C7 H7A 110.7 . . ? C6 C7 H7A 110.7 . . ? C8 C7 H7B 110.7 . . ? C6 C7 H7B 110.7 . . ? H7A C7 H7B 108.8 . . ? N9 C8 C7 104.0(3) . . ? N9 C8 H8A 111.0 . . ? C7 C8 H8A 111.0 . . ? N9 C8 H8B 111.0 . . ? C7 C8 H8B 111.0 . . ? H8A C8 H8B 109.0 . . ? C10 N9 C5A 127.7(3) . . ? C10 N9 C8 122.1(3) . . ? C5A N9 C8 110.1(3) . . ? O10 C10 N9 121.5(3) . . ? O10 C10 C10A 120.6(3) . . ? N9 C10 C10A 117.9(3) . . ? N4 C10A C10 113.1(3) . . ? N4 C10A C1 104.3(3) . . ? C10 C10A C1 112.1(3) . . ? N4 C10A C20A 108.0(2) . . ? C10 C10A C20A 106.4(3) . . ? C1 C10A C20A 113.0(3) . . ? C12 C11 C20A 106.1(3) . . ? C12 C11 H11A 110.5 . . ? C20A C11 H11A 110.5 . . ? C12 C11 H11B 110.5 . . ? C20A C11 H11B 110.5 . . ? H11A C11 H11B 108.7 . . ? C13 C12 C11 107.1(3) . . ? C13 C12 H12A 110.3 . . ? C11 C12 H12A 110.3 . . ? C13 C12 H12B 110.3 . . ? C11 C12 H12B 110.3 . . ? H12A C12 H12B 108.6 . . ? N14 C13 C12 102.1(3) . . ? N14 C13 H13A 111.3 . . ? C12 C13 H13A 111.3 . . ? N14 C13 H13B 111.3 . . ? C12 C13 H13B 111.3 . . ? H13A C13 H13B 109.2 . . ? C15 N14 C20A 126.1(3) . . ? C15 N14 C13 122.0(3) . . ? C20A N14 C13 111.9(3) . . ? O15 C15 N14 122.8(3) . . ? O15 C15 C15A 121.0(3) . . ? N14 C15 C15A 115.4(3) . . ? N19 C15A C15 114.0(3) . . ? N19 C15A C16 102.2(3) . . ? C15 C15A C16 120.2(3) . . ? N19 C15A S15 109.6(2) . . ? C15 C15A S15 106.0(2) . . ? C16 C15A S15 104.3(2) . . ? C15B S15 C15A 102.77(17) . . ? S15 C15B H15A 109.5 . . ? S15 C15B H15B 109.5 . . ? H15A C15B H15B 109.5 . . ? S15 C15B H15C 109.5 . . ? H15A C15B H15C 109.5 . . ? H15B C15B H15C 109.5 . . ? C15A C16 C17 103.6(3) . . ? C15A C16 H16A 111.0 . . ? C17 C16 H16A 111.0 . . ? C15A C16 H16B 111.0 . . ? C17 C16 H16B 111.0 . . ? H16A C16 H16B 109.0 . . ? C18 C17 C16 106.6(3) . . ? C18 C17 H17A 110.4 . . ? C16 C17 H17A 110.4 . . ? C18 C17 H17B 110.4 . . ? C16 C17 H17B 110.4 . . ? H17A C17 H17B 108.6 . . ? N19 C18 C17 104.0(3) . . ? N19 C18 H18A 111.0 . . ? C17 C18 H18A 111.0 . . ? N19 C18 H18B 111.0 . . ? C17 C18 H18B 111.0 . . ? H18A C18 H18B 109.0 . . ? C20 N19 C15A 128.7(3) . . ? C20 N19 C18 121.4(3) . . ? C15A N19 C18 109.1(3) . . ? O20 C20 N19 122.6(3) . . ? O20 C20 C20A 120.6(3) . . ? N19 C20 C20A 116.8(3) . . ? N14 C20A C20 112.0(3) . . ? N14 C20A C11 104.0(3) . . ? C20 C20A C11 111.1(3) . . ? N14 C20A C10A 108.9(2) . . ? C20 C20A C10A 107.6(3) . . ? C11 C20A C10A 113.3(3) . . ? C22 C21 C30A 106.9(3) . . ? C22 C21 H21A 110.3 . . ? C30A C21 H21A 110.3 . . ? C22 C21 H21B 110.3 . . ? C30A C21 H21B 110.3 . . ? H21A C21 H21B 108.6 . . ? C23 C22 C21 107.2(4) . . ? C23 C22 H22A 110.3 . . ? C21 C22 H22A 110.3 . . ? C23 C22 H22B 110.3 . . ? C21 C22 H22B 110.3 . . ? H22A C22 H22B 108.5 . . ? N24 C23 C22 103.1(3) . . ? N24 C23 H23A 111.1 . . ? C22 C23 H23A 111.1 . . ? N24 C23 H23B 111.1 . . ? C22 C23 H23B 111.1 . . ? H23A C23 H23B 109.1 . . ? C25 N24 C30A 126.3(3) . . ? C25 N24 C23 121.3(3) . . ? C30A N24 C23 112.2(3) . . ? O25 C25 N24 122.3(3) . . ? O25 C25 C25A 120.8(3) . . ? N24 C25 C25A 116.3(3) . . ? N29 C25A C25 113.9(3) . . ? N29 C25A C26 104.1(3) . . ? C25 C25A C26 117.8(3) . . ? N29 C25A S25 109.0(2) . . ? C25 C25A S25 105.9(3) . . ? C26 C25A S25 105.7(2) . . ? C25B S25 C25A 100.92(19) . . ? S25 C25B H25A 109.5 . . ? S25 C25B H25B 109.5 . . ? H25A C25B H25B 109.5 . . ? S25 C25B H25C 109.5 . . ? H25A C25B H25C 109.5 . . ? H25B C25B H25C 109.5 . . ? C25A C26 C27 104.3(3) . . ? C25A C26 H26A 110.9 . . ? C27 C26 H26A 110.9 . . ? C25A C26 H26B 110.9 . . ? C27 C26 H26B 110.9 . . ? H26A C26 H26B 108.9 . . ? C28 C27 C26 107.0(3) . . ? C28 C27 H27A 110.3 . . ? C26 C27 H27A 110.3 . . ? C28 C27 H27B 110.3 . . ? C26 C27 H27B 110.3 . . ? H27A C27 H27B 108.6 . . ? N29 C28 C27 103.3(3) . . ? N29 C28 H28A 111.1 . . ? C27 C28 H28A 111.1 . . ? N29 C28 H28B 111.1 . . ? C27 C28 H28B 111.1 . . ? H28A C28 H28B 109.1 . . ? C30 N29 C25A 128.0(3) . . ? C30 N29 C28 124.1(3) . . ? C25A N29 C28 107.9(3) . . ? O30 C30 N29 121.6(3) . . ? O30 C30 C30A 121.0(3) . . ? N29 C30 C30A 117.2(3) . . ? N24 C30A C30 112.2(3) . . ? N24 C30A C21 103.1(3) . . ? C30 C30A C21 112.2(3) . . ? N24 C30A C40A 108.8(3) . . ? C30 C30A C40A 107.5(3) . . ? C21 C30A C40A 113.0(3) . . ? C32 C31 C40A 106.1(4) . . ? C32 C31 H31A 110.5 . . ? C40A C31 H31A 110.5 . . ? C32 C31 H31B 110.5 . . ? C40A C31 H31B 110.5 . . ? H31A C31 H31B 108.7 . . ? C31 C32 C33 106.9(4) . . ? C31 C32 H32A 110.4 . . ? C33 C32 H32A 110.4 . . ? C31 C32 H32B 110.4 . . ? C33 C32 H32B 110.4 . . ? H32A C32 H32B 108.6 . . ? N34 C33 C32 102.5(4) . . ? N34 C33 H33A 111.3 . . ? C32 C33 H33A 111.3 . . ? N34 C33 H33B 111.3 . . ? C32 C33 H33B 111.3 . . ? H33A C33 H33B 109.2 . . ? C35 N34 C33 120.2(4) . . ? C35 N34 C40A 126.2(3) . . ? C33 N34 C40A 111.3(4) . . ? O35 C35 N34 122.9(4) . . ? O35 C35 C35A 120.0(4) . . ? N34 C35 C35A 116.7(3) . . ? N39 C35A C36 103.6(4) . . ? N39 C35A C35 114.0(3) . . ? C36 C35A C35 118.7(4) . . ? N39 C35A S35 103.2(2) . . ? C36 C35A S35 114.4(3) . . ? C35 C35A S35 102.3(3) . . ? C35B S35 C35A 104.9(2) . . ? S35 C35B H35A 109.5 . . ? S35 C35B H35B 109.5 . . ? H35A C35B H35B 109.5 . . ? S35 C35B H35C 109.5 . . ? H35A C35B H35C 109.5 . . ? H35B C35B H35C 109.5 . . ? C37 C36 C35A 104.8(4) . . ? C37 C36 H36A 110.8 . . ? C35A C36 H36A 110.8 . . ? C37 C36 H36B 110.8 . . ? C35A C36 H36B 110.8 . . ? H36A C36 H36B 108.9 . . ? C36 C37 C38 108.0(4) . . ? C36 C37 H37A 110.1 . . ? C38 C37 H37A 110.1 . . ? C36 C37 H37B 110.1 . . ? C38 C37 H37B 110.1 . . ? H37A C37 H37B 108.4 . . ? N39 C38 C37 102.2(4) . . ? N39 C38 H38A 111.3 . . ? C37 C38 H38A 111.3 . . ? N39 C38 H38B 111.3 . . ? C37 C38 H38B 111.3 . . ? H38A C38 H38B 109.2 . . ? C40 N39 C35A 127.7(3) . . ? C40 N39 C38 122.9(3) . . ? C35A N39 C38 109.4(3) . . ? O40 C40 N39 122.0(4) . . ? O40 C40 C40A 120.1(3) . . ? N39 C40 C40A 117.6(3) . . ? N34 C40A C40 113.0(3) . . ? N34 C40A C31 103.6(4) . . ? C40 C40A C31 110.7(3) . . ? N34 C40A C30A 107.9(3) . . ? C40 C40A C30A 108.8(3) . . ? C31 C40A C30A 112.8(3) . . ? H1W1 O1W H1W2 113(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C10A C1 C2 C3 -18.7(4) . . . . ? C1 C2 C3 N4 31.3(4) . . . . ? C2 C3 N4 C5 126.1(3) . . . . ? C2 C3 N4 C10A -33.9(3) . . . . ? C10A N4 C5 O5 -171.3(3) . . . . ? C3 N4 C5 O5 32.5(5) . . . . ? C10A N4 C5 C5A 16.7(5) . . . . ? C3 N4 C5 C5A -139.5(3) . . . . ? O5 C5 C5A N9 173.8(3) . . . . ? N4 C5 C5A N9 -14.0(4) . . . . ? O5 C5 C5A C6 52.0(5) . . . . ? N4 C5 C5A C6 -135.8(3) . . . . ? O5 C5 C5A S5 -73.3(3) . . . . ? N4 C5 C5A S5 98.9(3) . . . . ? N9 C5A S5 C5B -163.5(3) . . . . ? C5 C5A S5 C5B 76.9(3) . . . . ? C6 C5A S5 C5B -52.7(3) . . . . ? N9 C5A C6 C7 39.3(3) . . . . ? C5 C5A C6 C7 166.8(3) . . . . ? S5 C5A C6 C7 -73.0(3) . . . . ? C5A C6 C7 C8 -30.7(4) . . . . ? C6 C7 C8 N9 10.6(4) . . . . ? C5 C5A N9 C10 11.7(5) . . . . ? C6 C5A N9 C10 142.5(3) . . . . ? S5 C5A N9 C10 -99.7(3) . . . . ? C5 C5A N9 C8 -165.3(3) . . . . ? C6 C5A N9 C8 -34.5(3) . . . . ? S5 C5A N9 C8 83.4(3) . . . . ? C7 C8 N9 C10 -162.2(3) . . . . ? C7 C8 N9 C5A 15.0(4) . . . . ? C5A N9 C10 O10 173.9(3) . . . . ? C8 N9 C10 O10 -9.5(5) . . . . ? C5A N9 C10 C10A -9.4(5) . . . . ? C8 N9 C10 C10A 167.2(3) . . . . ? C5 N4 C10A C10 -13.6(4) . . . . ? C3 N4 C10A C10 144.4(3) . . . . ? C5 N4 C10A C1 -135.6(3) . . . . ? C3 N4 C10A C1 22.3(3) . . . . ? C5 N4 C10A C20A 103.9(3) . . . . ? C3 N4 C10A C20A -98.1(3) . . . . ? O10 C10 C10A N4 -174.6(3) . . . . ? N9 C10 C10A N4 8.7(4) . . . . ? O10 C10 C10A C1 -57.0(4) . . . . ? N9 C10 C10A C1 126.3(3) . . . . ? O10 C10 C10A C20A 67.0(4) . . . . ? N9 C10 C10A C20A -109.8(3) . . . . ? C2 C1 C10A N4 -1.5(3) . . . . ? C2 C1 C10A C10 -124.3(3) . . . . ? C2 C1 C10A C20A 115.5(3) . . . . ? C20A C11 C12 C13 -11.7(4) . . . . ? C11 C12 C13 N14 25.0(3) . . . . ? C12 C13 N14 C15 145.7(3) . . . . ? C12 C13 N14 C20A -31.1(3) . . . . ? C20A N14 C15 O15 -159.3(3) . . . . ? C13 N14 C15 O15 24.5(5) . . . . ? C20A N14 C15 C15A 30.8(4) . . . . ? C13 N14 C15 C15A -145.5(3) . . . . ? O15 C15 C15A N19 177.2(3) . . . . ? N14 C15 C15A N19 -12.6(4) . . . . ? O15 C15 C15A C16 55.4(5) . . . . ? N14 C15 C15A C16 -134.4(3) . . . . ? O15 C15 C15A S15 -62.2(4) . . . . ? N14 C15 C15A S15 108.0(3) . . . . ? N19 C15A S15 C15B 62.2(3) . . . . ? C15 C15A S15 C15B -61.2(3) . . . . ? C16 C15A S15 C15B 171.0(3) . . . . ? N19 C15A C16 C17 35.2(3) . . . . ? C15 C15A C16 C17 162.6(3) . . . . ? S15 C15A C16 C17 -78.9(3) . . . . ? C15A C16 C17 C18 -21.0(4) . . . . ? C16 C17 C18 N19 -1.3(4) . . . . ? C15 C15A N19 C20 0.1(5) . . . . ? C16 C15A N19 C20 131.4(4) . . . . ? S15 C15A N19 C20 -118.4(3) . . . . ? C15 C15A N19 C18 -169.5(3) . . . . ? C16 C15A N19 C18 -38.2(3) . . . . ? S15 C15A N19 C18 71.9(3) . . . . ? C17 C18 N19 C20 -145.7(3) . . . . ? C17 C18 N19 C15A 24.9(4) . . . . ? C15A N19 C20 O20 179.4(3) . . . . ? C18 N19 C20 O20 -12.1(5) . . . . ? C15A N19 C20 C20A -2.7(5) . . . . ? C18 N19 C20 C20A 165.8(3) . . . . ? C15 N14 C20A C20 -32.5(4) . . . . ? C13 N14 C20A C20 144.1(3) . . . . ? C15 N14 C20A C11 -152.5(3) . . . . ? C13 N14 C20A C11 24.1(3) . . . . ? C15 N14 C20A C10A 86.4(4) . . . . ? C13 N14 C20A C10A -97.0(3) . . . . ? O20 C20 C20A N14 -165.9(3) . . . . ? N19 C20 C20A N14 16.1(4) . . . . ? O20 C20 C20A C11 -50.1(4) . . . . ? N19 C20 C20A C11 131.9(3) . . . . ? O20 C20 C20A C10A 74.4(4) . . . . ? N19 C20 C20A C10A -103.5(3) . . . . ? C12 C11 C20A N14 -6.5(3) . . . . ? C12 C11 C20A C20 -127.2(3) . . . . ? C12 C11 C20A C10A 111.6(3) . . . . ? N4 C10A C20A N14 -70.3(3) . . . . ? C10 C10A C20A N14 51.4(3) . . . . ? C1 C10A C20A N14 174.8(3) . . . . ? N4 C10A C20A C20 51.3(3) . . . . ? C10 C10A C20A C20 173.0(3) . . . . ? C1 C10A C20A C20 -63.6(3) . . . . ? N4 C10A C20A C11 174.5(3) . . . . ? C10 C10A C20A C11 -63.8(3) . . . . ? C1 C10A C20A C11 59.6(4) . . . . ? C30A C21 C22 C23 5.0(5) . . . . ? C21 C22 C23 N24 -19.4(5) . . . . ? C22 C23 N24 C25 -145.5(4) . . . . ? C22 C23 N24 C30A 28.7(4) . . . . ? C30A N24 C25 O25 163.5(4) . . . . ? C23 N24 C25 O25 -23.1(6) . . . . ? C30A N24 C25 C25A -25.6(5) . . . . ? C23 N24 C25 C25A 147.8(3) . . . . ? O25 C25 C25A N29 -174.1(3) . . . . ? N24 C25 C25A N29 14.9(5) . . . . ? O25 C25 C25A C26 -51.8(5) . . . . ? N24 C25 C25A C26 137.2(4) . . . . ? O25 C25 C25A S25 66.2(4) . . . . ? N24 C25 C25A S25 -104.9(3) . . . . ? N29 C25A S25 C25B -62.4(3) . . . . ? C25 C25A S25 C25B 60.5(3) . . . . ? C26 C25A S25 C25B -173.8(3) . . . . ? N29 C25A C26 C27 -26.6(4) . . . . ? C25 C25A C26 C27 -153.7(3) . . . . ? S25 C25A C26 C27 88.2(3) . . . . ? C25A C26 C27 C28 6.5(4) . . . . ? C26 C27 C28 N29 15.0(4) . . . . ? C25 C25A N29 C30 -10.9(5) . . . . ? C26 C25A N29 C30 -140.5(4) . . . . ? S25 C25A N29 C30 107.0(4) . . . . ? C25 C25A N29 C28 167.3(3) . . . . ? C26 C25A N29 C28 37.8(3) . . . . ? S25 C25A N29 C28 -74.7(3) . . . . ? C27 C28 N29 C30 145.1(4) . . . . ? C27 C28 N29 C25A -33.3(4) . . . . ? C25A N29 C30 O30 -170.8(4) . . . . ? C28 N29 C30 O30 11.1(6) . . . . ? C25A N29 C30 C30A 14.0(6) . . . . ? C28 N29 C30 C30A -164.0(3) . . . . ? C25 N24 C30A C30 27.4(5) . . . . ? C23 N24 C30A C30 -146.5(3) . . . . ? C25 N24 C30A C21 148.4(4) . . . . ? C23 N24 C30A C21 -25.5(4) . . . . ? C25 N24 C30A C40A -91.3(4) . . . . ? C23 N24 C30A C40A 94.7(4) . . . . ? O30 C30 C30A N24 165.5(4) . . . . ? N29 C30 C30A N24 -19.3(5) . . . . ? O30 C30 C30A C21 49.9(5) . . . . ? N29 C30 C30A C21 -134.9(4) . . . . ? O30 C30 C30A C40A -75.0(5) . . . . ? N29 C30 C30A C40A 100.2(4) . . . . ? C22 C21 C30A N24 11.5(4) . . . . ? C22 C21 C30A C30 132.5(4) . . . . ? C22 C21 C30A C40A -105.7(4) . . . . ? C40A C31 C32 C33 16.5(6) . . . . ? C31 C32 C33 N34 -28.7(5) . . . . ? C32 C33 N34 C35 -132.1(4) . . . . ? C32 C33 N34 C40A 31.6(5) . . . . ? C33 N34 C35 O35 -32.5(6) . . . . ? C40A N34 C35 O35 166.3(4) . . . . ? C33 N34 C35 C35A 140.5(4) . . . . ? C40A N34 C35 C35A -20.7(6) . . . . ? O35 C35 C35A N39 -171.5(4) . . . . ? N34 C35 C35A N39 15.3(5) . . . . ? O35 C35 C35A C36 -49.0(6) . . . . ? N34 C35 C35A C36 137.7(4) . . . . ? O35 C35 C35A S35 77.9(4) . . . . ? N34 C35 C35A S35 -95.4(4) . . . . ? N39 C35A S35 C35B 173.1(3) . . . . ? C36 C35A S35 C35B 61.4(4) . . . . ? C35 C35A S35 C35B -68.3(3) . . . . ? N39 C35A C36 C37 -32.1(4) . . . . ? C35 C35A C36 C37 -159.6(4) . . . . ? S35 C35A C36 C37 79.5(4) . . . . ? C35A C36 C37 C38 18.4(5) . . . . ? C36 C37 C38 N39 2.0(5) . . . . ? C36 C35A N39 C40 -145.5(4) . . . . ? C35 C35A N39 C40 -15.1(6) . . . . ? S35 C35A N39 C40 95.0(4) . . . . ? C36 C35A N39 C38 35.1(4) . . . . ? C35 C35A N39 C38 165.5(3) . . . . ? S35 C35A N39 C38 -84.4(3) . . . . ? C37 C38 N39 C40 157.5(4) . . . . ? C37 C38 N39 C35A -23.0(4) . . . . ? C35A N39 C40 O40 -169.8(4) . . . . ? C38 N39 C40 O40 9.5(6) . . . . ? C35A N39 C40 C40A 16.9(6) . . . . ? C38 N39 C40 C40A -163.8(4) . . . . ? C35 N34 C40A C40 21.2(5) . . . . ? C33 N34 C40A C40 -141.4(3) . . . . ? C35 N34 C40A C31 141.1(4) . . . . ? C33 N34 C40A C31 -21.5(4) . . . . ? C35 N34 C40A C30A -99.1(4) . . . . ? C33 N34 C40A C30A 98.3(4) . . . . ? O40 C40 C40A N34 169.2(4) . . . . ? N39 C40 C40A N34 -17.4(5) . . . . ? O40 C40 C40A C31 53.6(5) . . . . ? N39 C40 C40A C31 -133.0(4) . . . . ? O40 C40 C40A C30A -71.0(4) . . . . ? N39 C40 C40A C30A 102.4(4) . . . . ? C32 C31 C40A N34 2.2(5) . . . . ? C32 C31 C40A C40 123.6(4) . . . . ? C32 C31 C40A C30A -114.2(4) . . . . ? N24 C30A C40A N34 68.7(4) . . . . ? C30 C30A C40A N34 -53.1(4) . . . . ? C21 C30A C40A N34 -177.4(3) . . . . ? N24 C30A C40A C40 -54.2(4) . . . . ? C30 C30A C40A C40 -176.0(3) . . . . ? C21 C30A C40A C40 59.7(4) . . . . ? N24 C30A C40A C31 -177.5(3) . . . . ? C30 C30A C40A C31 60.7(4) . . . . ? C21 C30A C40A C31 -63.6(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1W H1W1 O25 0.840(10) 1.92(7) 2.727(12) 160(20) . O1W H1W2 O40 0.840(10) 1.95(4) 2.778(12) 171(20) 1_455 C5B H5B1 O5 0.98 2.37 3.081(5) 128.7 . C1 H1B O20 0.99 2.44 3.017(4) 116.4 . C3 H3B O20 0.99 2.59 3.210(4) 120.9 . C6 H6A O15 0.99 2.57 3.490(4) 154.9 . C8 H8B O10 0.99 2.60 3.370(5) 135.1 2_777 C11 H11B O10 0.99 2.42 2.910(4) 110.0 . C13 H13A O15 0.99 2.42 3.326(4) 152.4 2_677 C13 H13B O10 0.99 2.51 3.074(4) 115.5 . C16 H16A O5 0.99 2.34 3.316(4) 166.7 . C18 H18B O20 0.99 2.55 3.361(5) 138.7 2_667 C21 H21A O40 0.99 2.45 2.945(5) 110.6 . C23 H23B O25 0.99 2.39 3.340(5) 160.5 2_656 C25B H25A O25 0.98 2.48 3.447(5) 167.8 2_656 C26 H26B O35 0.99 2.39 3.323(5) 157.0 . C31 H31A O30 0.99 2.39 2.975(6) 117.5 . C31 H31B O40 0.99 2.61 2.938(6) 99.6 . C35B H35A O5 0.98 2.58 3.528(5) 162.7 2_666 C35B H35C O35 0.98 2.39 3.027(6) 122.4 . C36 H36A O25 0.99 2.58 3.498(5) 155.1 . C36 H36B O5 0.99 2.53 3.497(5) 165.7 2_666 C22 H22B O1W 0.99 2.14 2.960(15) 138.8 2_656 C6 H6B O1W 0.99 2.55 3.331(12) 135.8 2_666 C5B H5B3 O1W 0.98 2.05 3.028(14) 175.0 2_666 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.503 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.069 #============================================================================== data_sb327_hy _database_code_depnum_ccdc_archive 'CCDC 846902' #TrackingRef '- crystal structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; hexadecahydropyrazino[1,2-a:4,5-a']diindole-6,13-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 N2 O2' _chemical_formula_sum 'C18 H26 N2 O2' _chemical_formula_weight 302.41 _chemical_absolute_configuration syn 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 6.430(1) _cell_length_b 11.207(2) _cell_length_c 21.269(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1532.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2781 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description needles _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 200 sec./deg., 1 deg., 2 sets, 382 frames ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15375 _diffrn_reflns_av_R_equivalents 0.1413 _diffrn_reflns_av_sigmaI/netI 0.1129 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 3.31 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2697 _reflns_number_gt 1802 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement EVALCCD _computing_data_reduction EVALCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The absolute configuration has not been established by anomalous dispersion effects in diffraction measurement on the crystal. The enantiome has been assigned by reference to an unchanging chiral centre in the synthetic procedure. Determination of absolute structure using Bayesian statistics on Bijvoet differences (Hooft, Straver and Spek, 2008): y = 0.3(14) (Platon: Spek, 2003). ; _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^)+(0.0284P)^2^+1.9748P] 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 -3(3) _refine_ls_number_reflns 2697 _refine_ls_number_parameters 199 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1287 _refine_ls_R_factor_gt 0.0779 _refine_ls_wR_factor_ref 0.1481 _refine_ls_wR_factor_gt 0.1326 _refine_ls_goodness_of_fit_ref 1.107 _refine_ls_restrained_S_all 1.107 _refine_ls_shift/su_max 0.000 _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 N1 N 0.9555(6) 0.5589(3) 0.93195(17) 0.0189(10) Uani 1 1 d . . . C2 C 0.9619(8) 0.4319(4) 0.9455(2) 0.0216(12) Uani 1 1 d . . . H2 H 0.9400 0.4174 0.9914 0.026 Uiso 1 1 calc R . . C3 C 0.7999(8) 0.3663(4) 0.9074(2) 0.0265(12) Uani 1 1 d . . . H3A H 0.7968 0.3999 0.8643 0.032 Uiso 1 1 calc R . . H3B H 0.6616 0.3796 0.9265 0.032 Uiso 1 1 calc R . . C4 C 0.8401(8) 0.2331(4) 0.9033(2) 0.0288(13) Uani 1 1 d . . . H4A H 0.8332 0.1975 0.9459 0.035 Uiso 1 1 calc R . . H4B H 0.7320 0.1950 0.8770 0.035 Uiso 1 1 calc R . . C5 C 1.0507(8) 0.2109(4) 0.8753(2) 0.0245(12) Uani 1 1 d . . . H5A H 1.0562 0.2448 0.8324 0.029 Uiso 1 1 calc R . . H5B H 1.0755 0.1239 0.8722 0.029 Uiso 1 1 calc R . . C6 C 1.2190(8) 0.2679(4) 0.9158(2) 0.0282(13) Uani 1 1 d . . . H6A H 1.2238 0.2266 0.9569 0.034 Uiso 1 1 calc R . . H6B H 1.3555 0.2566 0.8951 0.034 Uiso 1 1 calc R . . C7 C 1.1839(7) 0.3995(4) 0.9267(2) 0.0214(11) Uani 1 1 d . . . H7 H 1.2788 0.4256 0.9614 0.026 Uiso 1 1 calc R . . C8 C 1.2234(8) 0.4793(4) 0.8703(2) 0.0235(12) Uani 1 1 d . . . H8A H 1.3743 0.4918 0.8639 0.028 Uiso 1 1 calc R . . H8B H 1.1630 0.4443 0.8317 0.028 Uiso 1 1 calc R . . C9 C 1.1174(7) 0.5937(4) 0.8870(2) 0.0181(11) Uani 1 1 d . . . H9 H 1.2193 0.6472 0.9086 0.022 Uiso 1 1 calc R . . C10 C 1.0184(8) 0.6613(5) 0.8328(2) 0.0237(12) Uani 1 1 d . . . O10 O 1.0607(5) 0.6414(3) 0.77751(15) 0.0300(9) Uani 1 1 d . . . N11 N 0.8844(6) 0.7423(4) 0.85323(16) 0.0191(9) Uani 1 1 d . . . C12 C 0.7590(8) 0.8202(4) 0.8136(2) 0.0228(12) Uani 1 1 d . . . H12 H 0.8489 0.8589 0.7811 0.027 Uiso 1 1 calc R . . C13 C 0.5853(7) 0.7536(5) 0.7824(2) 0.0250(12) Uani 1 1 d . . . H13A H 0.5196 0.6993 0.8132 0.030 Uiso 1 1 calc R . . H13B H 0.6423 0.7045 0.7478 0.030 Uiso 1 1 calc R . . C14 C 0.4226(8) 0.8379(5) 0.7564(2) 0.0305(13) Uani 1 1 d . . . H14A H 0.4855 0.8884 0.7233 0.037 Uiso 1 1 calc R . . H14B H 0.3085 0.7912 0.7371 0.037 Uiso 1 1 calc R . . C15 C 0.3358(8) 0.9162(5) 0.8079(2) 0.0338(13) Uani 1 1 d . . . H15A H 0.2305 0.9710 0.7900 0.041 Uiso 1 1 calc R . . H15B H 0.2667 0.8659 0.8399 0.041 Uiso 1 1 calc R . . C16 C 0.5061(8) 0.9878(5) 0.8384(3) 0.0344(14) Uani 1 1 d . . . H16A H 0.4470 1.0323 0.8744 0.041 Uiso 1 1 calc R . . H16B H 0.5587 1.0471 0.8077 0.041 Uiso 1 1 calc R . . C17 C 0.6872(8) 0.9131(5) 0.8615(2) 0.0266(12) Uani 1 1 d . . . H17 H 0.8065 0.9681 0.8698 0.032 Uiso 1 1 calc R . . C18 C 0.6522(7) 0.8384(4) 0.9203(2) 0.0223(11) Uani 1 1 d . . . H18A H 0.6496 0.8891 0.9585 0.027 Uiso 1 1 calc R . . H18B H 0.5203 0.7932 0.9176 0.027 Uiso 1 1 calc R . . C19 C 0.8364(7) 0.7559(4) 0.9209(2) 0.0237(11) Uani 1 1 d . . . H19 H 0.9558 0.7960 0.9424 0.028 Uiso 1 1 calc R . . C20 C 0.8047(8) 0.6339(4) 0.9487(2) 0.0229(12) Uani 1 1 d . . . O20 O 0.6593(5) 0.6077(3) 0.98342(15) 0.0309(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 N1 0.021(2) 0.018(2) 0.018(2) 0.0020(17) 0.0018(18) -0.0002(19) C2 0.024(3) 0.023(3) 0.018(3) 0.002(2) -0.002(2) 0.002(2) C3 0.020(3) 0.030(3) 0.029(3) 0.000(2) -0.003(2) -0.004(3) C4 0.025(3) 0.025(3) 0.037(3) -0.003(2) -0.002(2) 0.004(3) C5 0.030(3) 0.014(3) 0.029(3) -0.003(2) -0.002(2) 0.005(2) C6 0.024(3) 0.026(3) 0.035(3) 0.000(2) -0.005(2) 0.001(3) C7 0.015(3) 0.019(3) 0.029(3) 0.000(2) -0.006(2) -0.002(2) C8 0.014(3) 0.028(3) 0.029(3) -0.001(2) 0.003(2) 0.000(2) C9 0.013(3) 0.022(3) 0.019(2) -0.001(2) -0.002(2) -0.004(2) C10 0.021(3) 0.026(3) 0.025(3) 0.000(2) 0.001(2) -0.007(3) O10 0.028(2) 0.038(2) 0.025(2) 0.0017(17) 0.0048(16) -0.0001(18) N11 0.019(2) 0.020(2) 0.018(2) 0.0009(18) -0.0034(17) -0.0008(19) C12 0.023(3) 0.023(3) 0.023(3) 0.008(2) 0.000(2) -0.001(2) C13 0.022(3) 0.030(3) 0.023(3) -0.004(2) 0.003(2) -0.007(3) C14 0.025(3) 0.035(3) 0.031(3) 0.006(3) -0.008(2) -0.009(3) C15 0.025(3) 0.033(3) 0.044(3) 0.009(3) -0.006(3) 0.002(3) C16 0.025(3) 0.026(3) 0.051(4) 0.007(3) -0.002(3) 0.002(3) C17 0.026(3) 0.020(3) 0.034(3) 0.001(2) -0.009(2) 0.001(2) C18 0.023(3) 0.023(3) 0.021(3) -0.005(2) -0.001(2) 0.003(2) C19 0.024(3) 0.027(3) 0.020(3) -0.002(2) 0.000(2) 0.004(3) C20 0.031(3) 0.024(3) 0.013(2) -0.008(2) -0.002(2) 0.000(3) O20 0.031(2) 0.032(2) 0.0301(19) 0.0031(16) 0.0173(18) 0.0048(19) _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 N1 C20 1.332(6) . ? N1 C2 1.453(6) . ? N1 C9 1.466(6) . ? C2 C3 1.511(6) . ? C2 C7 1.526(7) . ? C2 H2 1.0000 . ? C3 C4 1.517(7) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.500(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.523(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.510(7) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.517(6) . ? C7 H7 1.0000 . ? C8 C9 1.495(6) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.519(7) . ? C9 H9 1.0000 . ? C10 O10 1.228(5) . ? C10 N11 1.325(6) . ? N11 C12 1.456(6) . ? N11 C19 1.479(5) . ? C12 C13 1.499(6) . ? C12 C17 1.527(7) . ? C12 H12 1.0000 . ? C13 C14 1.514(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.511(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.504(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.516(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.522(6) . ? C17 H17 1.0000 . ? C18 C19 1.503(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.504(7) . ? C19 H19 1.0000 . ? C20 O20 1.227(6) . ? 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 C20 N1 C2 125.9(4) . . ? C20 N1 C9 121.6(4) . . ? C2 N1 C9 111.7(4) . . ? N1 C2 C3 110.6(4) . . ? N1 C2 C7 102.0(4) . . ? C3 C2 C7 112.9(4) . . ? N1 C2 H2 110.4 . . ? C3 C2 H2 110.4 . . ? C7 C2 H2 110.4 . . ? C2 C3 C4 113.1(4) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 109.9(4) . . ? C5 C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C5 C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C4 C5 C6 110.3(4) . . ? C4 C5 H5A 109.6 . . ? C6 C5 H5A 109.6 . . ? C4 C5 H5B 109.6 . . ? C6 C5 H5B 109.6 . . ? H5A C5 H5B 108.1 . . ? C7 C6 C5 113.0(4) . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 115.4(4) . . ? C6 C7 C2 114.3(4) . . ? C8 C7 C2 102.9(4) . . ? C6 C7 H7 107.9 . . ? C8 C7 H7 107.9 . . ? C2 C7 H7 107.9 . . ? C9 C8 C7 104.0(4) . . ? C9 C8 H8A 111.0 . . ? C7 C8 H8A 111.0 . . ? C9 C8 H8B 111.0 . . ? C7 C8 H8B 111.0 . . ? H8A C8 H8B 109.0 . . ? N1 C9 C8 104.5(4) . . ? N1 C9 C10 109.2(4) . . ? C8 C9 C10 116.1(4) . . ? N1 C9 H9 108.9 . . ? C8 C9 H9 108.9 . . ? C10 C9 H9 108.9 . . ? O10 C10 N11 125.6(5) . . ? O10 C10 C9 122.9(5) . . ? N11 C10 C9 111.5(4) . . ? C10 N11 C12 125.6(4) . . ? C10 N11 C19 121.7(4) . . ? C12 N11 C19 112.7(4) . . ? N11 C12 C13 111.8(4) . . ? N11 C12 C17 101.0(4) . . ? C13 C12 C17 114.2(4) . . ? N11 C12 H12 109.9 . . ? C13 C12 H12 109.9 . . ? C17 C12 H12 109.9 . . ? C12 C13 C14 111.5(4) . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 110.6(4) . . ? C15 C14 H14A 109.5 . . ? C13 C14 H14A 109.5 . . ? C15 C14 H14B 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C14 110.7(5) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 113.8(5) . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C16 C17 C18 117.2(4) . . ? C16 C17 C12 113.1(4) . . ? C18 C17 C12 102.6(4) . . ? C16 C17 H17 107.8 . . ? C18 C17 H17 107.8 . . ? C12 C17 H17 107.8 . . ? C19 C18 C17 103.2(4) . . ? C19 C18 H18A 111.1 . . ? C17 C18 H18A 111.1 . . ? C19 C18 H18B 111.1 . . ? C17 C18 H18B 111.1 . . ? H18A C18 H18B 109.1 . . ? N11 C19 C18 102.7(4) . . ? N11 C19 C20 108.5(4) . . ? C18 C19 C20 117.1(4) . . ? N11 C19 H19 109.4 . . ? C18 C19 H19 109.4 . . ? C20 C19 H19 109.4 . . ? O20 C20 N1 124.3(4) . . ? O20 C20 C19 123.9(4) . . ? N1 C20 C19 111.7(4) . . ? 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 C20 N1 C2 C3 70.2(6) . . . . ? C9 N1 C2 C3 -99.2(5) . . . . ? C20 N1 C2 C7 -169.5(4) . . . . ? C9 N1 C2 C7 21.1(5) . . . . ? N1 C2 C3 C4 162.1(4) . . . . ? C7 C2 C3 C4 48.6(6) . . . . ? C2 C3 C4 C5 -57.8(5) . . . . ? C3 C4 C5 C6 60.0(5) . . . . ? C4 C5 C6 C7 -55.1(6) . . . . ? C5 C6 C7 C8 -72.6(6) . . . . ? C5 C6 C7 C2 46.4(6) . . . . ? N1 C2 C7 C6 -161.5(4) . . . . ? C3 C2 C7 C6 -42.9(6) . . . . ? N1 C2 C7 C8 -35.6(4) . . . . ? C3 C2 C7 C8 83.1(5) . . . . ? C6 C7 C8 C9 163.1(4) . . . . ? C2 C7 C8 C9 37.9(5) . . . . ? C20 N1 C9 C8 -167.6(4) . . . . ? C2 N1 C9 C8 2.3(5) . . . . ? C20 N1 C9 C10 -42.8(6) . . . . ? C2 N1 C9 C10 127.1(4) . . . . ? C7 C8 C9 N1 -25.0(5) . . . . ? C7 C8 C9 C10 -145.4(4) . . . . ? N1 C9 C10 O10 -134.4(5) . . . . ? C8 C9 C10 O10 -16.7(7) . . . . ? N1 C9 C10 N11 45.6(5) . . . . ? C8 C9 C10 N11 163.4(4) . . . . ? O10 C10 N11 C12 1.7(8) . . . . ? C9 C10 N11 C12 -178.4(4) . . . . ? O10 C10 N11 C19 177.1(5) . . . . ? C9 C10 N11 C19 -3.0(6) . . . . ? C10 N11 C12 C13 73.3(6) . . . . ? C19 N11 C12 C13 -102.4(4) . . . . ? C10 N11 C12 C17 -164.9(4) . . . . ? C19 N11 C12 C17 19.3(5) . . . . ? N11 C12 C13 C14 164.3(4) . . . . ? C17 C12 C13 C14 50.4(5) . . . . ? C12 C13 C14 C15 -57.7(6) . . . . ? C13 C14 C15 C16 58.8(6) . . . . ? C14 C15 C16 C17 -53.2(6) . . . . ? C15 C16 C17 C18 -73.5(6) . . . . ? C15 C16 C17 C12 45.5(6) . . . . ? N11 C12 C17 C16 -164.2(4) . . . . ? C13 C12 C17 C16 -44.2(6) . . . . ? N11 C12 C17 C18 -37.0(5) . . . . ? C13 C12 C17 C18 83.0(5) . . . . ? C16 C17 C18 C19 166.9(4) . . . . ? C12 C17 C18 C19 42.3(5) . . . . ? C10 N11 C19 C18 -169.5(4) . . . . ? C12 N11 C19 C18 6.5(5) . . . . ? C10 N11 C19 C20 -44.9(6) . . . . ? C12 N11 C19 C20 131.1(4) . . . . ? C17 C18 C19 N11 -29.8(5) . . . . ? C17 C18 C19 C20 -148.6(4) . . . . ? C2 N1 C20 O20 7.5(7) . . . . ? C9 N1 C20 O20 176.0(4) . . . . ? C2 N1 C20 C19 -173.6(4) . . . . ? C9 N1 C20 C19 -5.2(6) . . . . ? N11 C19 C20 O20 -133.6(5) . . . . ? C18 C19 C20 O20 -18.0(7) . . . . ? N11 C19 C20 N1 47.6(5) . . . . ? C18 C19 C20 N1 163.2(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C14 H14B O10 0.99 2.47 3.234(6) 133.9 1_455 C19 H19 O20 1.00 2.32 3.285(6) 162.7 4_567 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.249 _refine_diff_density_min -0.280 _refine_diff_density_rms 0.062 #============================================================================== data_sb343_hy _database_code_depnum_ccdc_archive 'CCDC 846903' #TrackingRef '- crystal structures.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; dodecahydro-6a,13a-epidithiopyrazino[1,2-a:4,5-a']diindole-6,13(1H,7H)-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H24 N2 O2 S2' _chemical_formula_sum 'C18 H24 N2 O2 S2' _chemical_formula_weight 364.51 _chemical_absolute_configuration ad 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' 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 6.4416(6) _cell_length_b 10.8045(5) _cell_length_c 24.627(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1714.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 214 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.0 _exptl_crystal_description plates _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.324 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8165 _exptl_absorpt_correction_T_max 0.9803 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; dx = 45 mm, 200 sec./deg., 1 deg., 1 sets, 363 fraems, 7409 refl. postref. ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'rotation in phi, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12711 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0403 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3924 _reflns_number_gt 3471 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement EVALCCD _computing_data_reduction EVALCCD _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Determination of absolute structure using Bayesian statistics on Bijvoet differences (Hooft, Straver and Spek, 2008): FLEQ = 0.05(03) (Platon: Spek, 2003). ; _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^)+(0.0289P)^2^+0.5072P] 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 0.07(6) _refine_ls_number_reflns 3924 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0353 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0712 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _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 S1 S 0.15554(8) 0.40109(5) 0.35828(2) 0.02341(12) Uani 1 1 d . . . S2 S 0.03469(8) 0.48134(5) 0.42756(2) 0.02495(13) Uani 1 1 d . . . N1 N 0.4224(3) 0.59478(15) 0.37241(6) 0.0195(4) Uani 1 1 d . . . C2 C 0.5060(3) 0.66359(18) 0.32620(8) 0.0203(4) Uani 1 1 d . . . H2 H 0.4154 0.7361 0.3175 0.024 Uiso 1 1 calc R . . C3 C 0.7262(3) 0.7058(2) 0.33791(8) 0.0218(5) Uani 1 1 d . . . H3A H 0.7222 0.7773 0.3630 0.026 Uiso 1 1 calc R . . H3B H 0.8027 0.6381 0.3561 0.026 Uiso 1 1 calc R . . C4 C 0.8402(4) 0.7424(2) 0.28670(8) 0.0264(5) Uani 1 1 d . . . H4A H 0.9836 0.7678 0.2959 0.032 Uiso 1 1 calc R . . H4B H 0.7695 0.8139 0.2696 0.032 Uiso 1 1 calc R . . C5 C 0.8462(4) 0.6349(2) 0.24696(8) 0.0256(5) Uani 1 1 d . . . H5A H 0.9202 0.6607 0.2136 0.031 Uiso 1 1 calc R . . H5B H 0.9238 0.5652 0.2633 0.031 Uiso 1 1 calc R . . C6 C 0.6292(3) 0.5924(2) 0.23233(8) 0.0239(4) Uani 1 1 d . . . H6A H 0.6393 0.5162 0.2101 0.029 Uiso 1 1 calc R . . H6B H 0.5621 0.6568 0.2098 0.029 Uiso 1 1 calc R . . C7 C 0.4926(3) 0.56639(18) 0.28127(8) 0.0210(4) Uani 1 1 d . . . H7 H 0.3454 0.5628 0.2685 0.025 Uiso 1 1 calc R . . C8 C 0.5393(3) 0.44635(18) 0.31154(7) 0.0196(4) Uani 1 1 d . . . H8A H 0.4859 0.3737 0.2914 0.023 Uiso 1 1 calc R . . H8B H 0.6902 0.4361 0.3176 0.023 Uiso 1 1 calc R . . C9 C 0.4248(3) 0.46367(18) 0.36470(8) 0.0184(4) Uani 1 1 d . . . C10 C 0.5124(3) 0.39686(18) 0.41370(7) 0.0173(4) Uani 1 1 d . . . O10 O 0.6372(2) 0.31286(12) 0.41040(5) 0.0230(3) Uani 1 1 d . . . N11 N 0.4323(3) 0.44209(14) 0.45969(6) 0.0176(4) Uani 1 1 d . . . C12 C 0.4753(3) 0.40187(18) 0.51542(7) 0.0168(4) Uani 1 1 d . . . H12 H 0.4745 0.3095 0.5176 0.020 Uiso 1 1 calc R . . C13 C 0.6832(3) 0.4521(2) 0.53405(8) 0.0198(4) Uani 1 1 d . . . H13A H 0.7956 0.4015 0.5179 0.024 Uiso 1 1 calc R . . H13B H 0.6994 0.5379 0.5206 0.024 Uiso 1 1 calc R . . C14 C 0.7058(3) 0.4515(2) 0.59524(8) 0.0223(4) Uani 1 1 d . . . H14A H 0.7025 0.3652 0.6088 0.027 Uiso 1 1 calc R . . H14B H 0.8408 0.4884 0.6055 0.027 Uiso 1 1 calc R . . C15 C 0.5317(3) 0.52438(18) 0.62059(8) 0.0202(4) Uani 1 1 d . . . H15A H 0.5361 0.6108 0.6072 0.024 Uiso 1 1 calc R . . H15B H 0.5495 0.5259 0.6605 0.024 Uiso 1 1 calc R . . C16 C 0.3243(3) 0.46724(19) 0.60666(7) 0.0190(4) Uani 1 1 d . . . H16A H 0.2123 0.5189 0.6223 0.023 Uiso 1 1 calc R . . H16B H 0.3155 0.3842 0.6235 0.023 Uiso 1 1 calc R . . C17 C 0.2897(3) 0.45496(19) 0.54595(8) 0.0184(4) Uani 1 1 d . . . H17 H 0.1695 0.3979 0.5402 0.022 Uiso 1 1 calc R . . C18 C 0.2441(3) 0.57496(19) 0.51561(8) 0.0206(4) Uani 1 1 d . . . H18A H 0.0988 0.6017 0.5213 0.025 Uiso 1 1 calc R . . H18B H 0.3388 0.6420 0.5273 0.025 Uiso 1 1 calc R . . C19 C 0.2819(3) 0.54030(19) 0.45707(8) 0.0196(4) Uani 1 1 d . . . C20 C 0.3518(3) 0.64244(18) 0.41949(8) 0.0193(4) Uani 1 1 d . . . O20 O 0.3430(2) 0.75200(12) 0.43004(6) 0.0243(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 S1 0.0224(2) 0.0251(3) 0.0227(2) -0.0019(2) -0.0044(2) -0.0031(2) S2 0.0176(2) 0.0346(3) 0.0227(2) 0.0000(2) -0.0030(2) 0.0010(2) N1 0.0277(9) 0.0129(8) 0.0181(8) 0.0010(7) -0.0013(6) 0.0010(7) C2 0.0258(11) 0.0175(10) 0.0176(9) 0.0020(8) -0.0021(8) 0.0027(9) C3 0.0285(11) 0.0193(11) 0.0175(10) -0.0011(8) -0.0029(8) -0.0013(9) C4 0.0292(12) 0.0250(11) 0.0250(10) 0.0007(9) -0.0026(10) -0.0066(10) C5 0.0297(11) 0.0274(11) 0.0198(10) 0.0009(9) 0.0023(9) -0.0006(10) C6 0.0318(11) 0.0216(10) 0.0183(9) 0.0016(9) -0.0028(8) -0.0010(10) C7 0.0237(11) 0.0209(10) 0.0183(9) 0.0001(8) -0.0035(8) -0.0005(8) C8 0.0240(10) 0.0163(10) 0.0184(9) -0.0022(8) -0.0009(8) -0.0008(9) C9 0.0185(9) 0.0143(10) 0.0226(10) -0.0031(8) -0.0026(8) -0.0016(8) C10 0.0190(9) 0.0137(9) 0.0193(9) -0.0006(8) -0.0027(7) -0.0030(8) O10 0.0273(8) 0.0169(7) 0.0248(7) -0.0024(6) -0.0020(6) 0.0067(7) N11 0.0213(8) 0.0139(8) 0.0175(8) -0.0001(7) -0.0014(7) 0.0037(7) C12 0.0206(9) 0.0134(9) 0.0164(9) 0.0025(8) -0.0008(8) 0.0010(9) C13 0.0177(10) 0.0219(11) 0.0198(9) -0.0018(8) 0.0008(8) 0.0008(8) C14 0.0210(10) 0.0246(12) 0.0214(10) 0.0010(9) -0.0040(8) -0.0010(8) C15 0.0207(9) 0.0204(10) 0.0194(9) -0.0008(8) -0.0009(8) -0.0015(9) C16 0.0218(10) 0.0181(11) 0.0170(9) 0.0006(8) 0.0028(8) -0.0046(9) C17 0.0152(9) 0.0169(10) 0.0230(10) 0.0007(8) -0.0004(7) -0.0015(8) C18 0.0188(9) 0.0205(11) 0.0225(10) -0.0016(9) -0.0004(8) 0.0027(9) C19 0.0161(9) 0.0205(11) 0.0220(10) -0.0011(9) -0.0029(7) 0.0039(8) C20 0.0182(9) 0.0186(10) 0.0210(10) -0.0001(8) -0.0026(8) 0.0031(8) O20 0.0327(8) 0.0161(7) 0.0240(7) -0.0008(6) 0.0003(7) 0.0066(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C9 1.8684(19) . ? S1 S2 2.0661(8) . ? S2 C19 1.863(2) . ? N1 C20 1.348(2) . ? N1 C9 1.429(3) . ? N1 C2 1.462(2) . ? C2 C3 1.518(3) . ? C2 C7 1.528(3) . ? C2 H2 1.0000 . ? C3 C4 1.512(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.520(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.515(3) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.518(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.526(3) . ? C7 H7 1.0000 . ? C8 C9 1.514(3) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.515(3) . ? C10 O10 1.215(2) . ? C10 N11 1.337(2) . ? N11 C19 1.438(2) . ? N11 C12 1.466(2) . ? C12 C13 1.516(3) . ? C12 C17 1.524(3) . ? C12 H12 1.0000 . ? C13 C14 1.514(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.506(3) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.511(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.517(3) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.525(3) . ? C17 H17 1.0000 . ? C18 C19 1.509(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.509(3) . ? C20 O20 1.213(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 S1 S2 97.36(7) . . ? C19 S2 S1 98.26(7) . . ? C20 N1 C9 119.78(16) . . ? C20 N1 C2 126.84(16) . . ? C9 N1 C2 113.36(15) . . ? N1 C2 C3 110.43(16) . . ? N1 C2 C7 101.15(15) . . ? C3 C2 C7 113.38(17) . . ? N1 C2 H2 110.5 . . ? C3 C2 H2 110.5 . . ? C7 C2 H2 110.5 . . ? C4 C3 C2 111.97(17) . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3B 109.2 . . ? C2 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C5 110.46(17) . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4B 109.6 . . ? C5 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C6 C5 C4 111.19(19) . . ? C6 C5 H5A 109.4 . . ? C4 C5 H5A 109.4 . . ? C6 C5 H5B 109.4 . . ? C4 C5 H5B 109.4 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C7 113.70(16) . . ? C5 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? C5 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 C8 115.53(17) . . ? C6 C7 C2 114.53(17) . . ? C8 C7 C2 102.67(15) . . ? C6 C7 H7 107.9 . . ? C8 C7 H7 107.9 . . ? C2 C7 H7 107.9 . . ? C9 C8 C7 102.80(16) . . ? C9 C8 H8A 111.2 . . ? C7 C8 H8A 111.2 . . ? C9 C8 H8B 111.2 . . ? C7 C8 H8B 111.2 . . ? H8A C8 H8B 109.1 . . ? N1 C9 C8 104.05(16) . . ? N1 C9 C10 111.74(16) . . ? C8 C9 C10 116.64(16) . . ? N1 C9 S1 111.08(13) . . ? C8 C9 S1 109.52(13) . . ? C10 C9 S1 103.94(13) . . ? O10 C10 N11 125.80(17) . . ? O10 C10 C9 123.30(17) . . ? N11 C10 C9 110.90(16) . . ? C10 N11 C19 119.45(15) . . ? C10 N11 C12 127.71(16) . . ? C19 N11 C12 112.82(14) . . ? N11 C12 C13 110.12(16) . . ? N11 C12 C17 101.67(15) . . ? C13 C12 C17 114.13(15) . . ? N11 C12 H12 110.2 . . ? C13 C12 H12 110.2 . . ? C17 C12 H12 110.2 . . ? C14 C13 C12 112.60(16) . . ? C14 C13 H13A 109.1 . . ? C12 C13 H13A 109.1 . . ? C14 C13 H13B 109.1 . . ? C12 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C15 C14 C13 109.82(17) . . ? C15 C14 H14A 109.7 . . ? C13 C14 H14A 109.7 . . ? C15 C14 H14B 109.7 . . ? C13 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? C14 C15 C16 110.51(16) . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C16 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 112.91(16) . . ? C15 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? C15 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 C12 113.82(16) . . ? C16 C17 C18 115.89(17) . . ? C12 C17 C18 103.25(16) . . ? C16 C17 H17 107.8 . . ? C12 C17 H17 107.8 . . ? C18 C17 H17 107.8 . . ? C19 C18 C17 103.07(16) . . ? C19 C18 H18A 111.1 . . ? C17 C18 H18A 111.1 . . ? C19 C18 H18B 111.1 . . ? C17 C18 H18B 111.1 . . ? H18A C18 H18B 109.1 . . ? N11 C19 C20 111.47(16) . . ? N11 C19 C18 104.40(15) . . ? C20 C19 C18 116.90(17) . . ? N11 C19 S2 109.94(13) . . ? C20 C19 S2 105.43(13) . . ? C18 C19 S2 108.66(14) . . ? O20 C20 N1 124.94(18) . . ? O20 C20 C19 124.64(18) . . ? N1 C20 C19 110.42(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 S1 S2 C19 -9.21(9) . . . . ? C20 N1 C2 C3 76.7(2) . . . . ? C9 N1 C2 C3 -101.71(19) . . . . ? C20 N1 C2 C7 -162.95(19) . . . . ? C9 N1 C2 C7 18.6(2) . . . . ? N1 C2 C3 C4 162.87(17) . . . . ? C7 C2 C3 C4 50.2(2) . . . . ? C2 C3 C4 C5 -58.1(2) . . . . ? C3 C4 C5 C6 58.6(2) . . . . ? C4 C5 C6 C7 -51.6(2) . . . . ? C5 C6 C7 C8 -75.1(2) . . . . ? C5 C6 C7 C2 44.0(2) . . . . ? N1 C2 C7 C6 -161.20(16) . . . . ? C3 C2 C7 C6 -43.0(2) . . . . ? N1 C2 C7 C8 -35.17(19) . . . . ? C3 C2 C7 C8 83.1(2) . . . . ? C6 C7 C8 C9 165.05(16) . . . . ? C2 C7 C8 C9 39.7(2) . . . . ? C20 N1 C9 C8 -172.54(17) . . . . ? C2 N1 C9 C8 6.0(2) . . . . ? C20 N1 C9 C10 -45.9(3) . . . . ? C2 N1 C9 C10 132.69(17) . . . . ? C20 N1 C9 S1 69.7(2) . . . . ? C2 N1 C9 S1 -111.74(16) . . . . ? C7 C8 C9 N1 -28.23(19) . . . . ? C7 C8 C9 C10 -151.78(16) . . . . ? C7 C8 C9 S1 90.59(16) . . . . ? S2 S1 C9 N1 -51.52(14) . . . . ? S2 S1 C9 C8 -165.89(12) . . . . ? S2 S1 C9 C10 68.79(12) . . . . ? N1 C9 C10 O10 -135.43(19) . . . . ? C8 C9 C10 O10 -15.9(3) . . . . ? S1 C9 C10 O10 104.71(19) . . . . ? N1 C9 C10 N11 45.2(2) . . . . ? C8 C9 C10 N11 164.73(16) . . . . ? S1 C9 C10 N11 -74.63(17) . . . . ? O10 C10 N11 C19 -178.58(19) . . . . ? C9 C10 N11 C19 0.7(2) . . . . ? O10 C10 N11 C12 0.0(3) . . . . ? C9 C10 N11 C12 179.32(17) . . . . ? C10 N11 C12 C13 77.2(2) . . . . ? C19 N11 C12 C13 -104.12(18) . . . . ? C10 N11 C12 C17 -161.44(18) . . . . ? C19 N11 C12 C17 17.2(2) . . . . ? N11 C12 C13 C14 160.90(17) . . . . ? C17 C12 C13 C14 47.3(2) . . . . ? C12 C13 C14 C15 -56.8(2) . . . . ? C13 C14 C15 C16 60.9(2) . . . . ? C14 C15 C16 C17 -56.1(2) . . . . ? C15 C16 C17 C12 46.1(2) . . . . ? C15 C16 C17 C18 -73.5(2) . . . . ? N11 C12 C17 C16 -160.12(16) . . . . ? C13 C12 C17 C16 -41.6(2) . . . . ? N11 C12 C17 C18 -33.66(18) . . . . ? C13 C12 C17 C18 84.85(19) . . . . ? C16 C17 C18 C19 163.56(16) . . . . ? C12 C17 C18 C19 38.43(19) . . . . ? C10 N11 C19 C20 -47.5(2) . . . . ? C12 N11 C19 C20 133.70(17) . . . . ? C10 N11 C19 C18 -174.60(17) . . . . ? C12 N11 C19 C18 6.6(2) . . . . ? C10 N11 C19 S2 69.0(2) . . . . ? C12 N11 C19 S2 -109.77(15) . . . . ? C17 C18 C19 N11 -27.73(19) . . . . ? C17 C18 C19 C20 -151.37(17) . . . . ? C17 C18 C19 S2 89.54(16) . . . . ? S1 S2 C19 N11 -51.80(13) . . . . ? S1 S2 C19 C20 68.47(13) . . . . ? S1 S2 C19 C18 -165.48(13) . . . . ? C9 N1 C20 O20 -179.89(18) . . . . ? C2 N1 C20 O20 1.8(3) . . . . ? C9 N1 C20 C19 -0.8(3) . . . . ? C2 N1 C20 C19 -179.10(17) . . . . ? N11 C19 C20 O20 -134.2(2) . . . . ? C18 C19 C20 O20 -14.2(3) . . . . ? S2 C19 C20 O20 106.6(2) . . . . ? N11 C19 C20 N1 46.7(2) . . . . ? C18 C19 C20 N1 166.64(17) . . . . ? S2 C19 C20 N1 -72.56(18) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C3 H3B S2 0.99 2.86 3.835(2) 167.3 1_655 C13 H13A S2 0.99 2.84 3.479(2) 122.9 1_655 C16 H16B O10 0.99 2.56 3.285(2) 130.0 4_456 C17 H17 O10 1.00 2.59 3.239(2) 122.6 4_456 C18 H18A O20 0.99 2.58 3.459(2) 148.2 4_466 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.253 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.047 #============================================================================== #_eof # End of Crystallographic Information File #============================================================================== data_sb344 _database_code_depnum_ccdc_archive 'CCDC 852472' #TrackingRef 'obc_bmr_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6a,13a-bis(methylthio)hexadecahydropyrazino[1,2-a:4,5-a']diindole-6,13-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 N2 O2 S2' _chemical_formula_sum 'C20 H30 N2 O2 S2' _chemical_formula_weight 394.58 _chemical_absolute_configuration ad 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 triclinic _symmetry_space_group_name_H-M 'P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 9.1262(9) _cell_length_b 9.6454(10) _cell_length_c 11.5103(9) _cell_angle_alpha 91.426(5) _cell_angle_beta 101.320(6) _cell_angle_gamma 91.777(5) _cell_volume 992.52(16) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 2972 _cell_measurement_theta_min 1 _cell_measurement_theta_max 25 _exptl_crystal_description rods _exptl_crystal_colour colourless _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.286 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 90 sec./deg. 0.5 deg., 5 sets, 717 frames ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius APEXII' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5890 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0935 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 24.96 _reflns_number_total 4287 _reflns_number_gt 3442 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Due to the bad quality (due to the shape and size of the crystal) of the data general ISOR-restraints have to be used. Determination of absolute structure using Bayesian statistics on Bijvoet differences (Hooft, Straver and Spek, 2008): FLEQ/y = 0.03(10) (Platon: Spek, 2003). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^2^+9.0000P] 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 0.0(2) _refine_ls_number_reflns 4287 _refine_ls_number_parameters 473 _refine_ls_number_restraints 315 _refine_ls_R_factor_all 0.1323 _refine_ls_R_factor_gt 0.1008 _refine_ls_wR_factor_ref 0.2264 _refine_ls_wR_factor_gt 0.2044 _refine_ls_goodness_of_fit_ref 1.166 _refine_ls_restrained_S_all 1.133 _refine_ls_shift/su_max 0.000 _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 S1 S 0.3123(4) 0.1669(4) 0.5919(3) 0.0328(9) Uani 1 1 d U . . S2 S 0.2928(4) 0.2938(4) 0.8622(3) 0.0349(9) Uani 1 1 d U . . N1 N 0.5792(11) 0.1603(10) 0.7442(8) 0.021(2) Uani 1 1 d U . . C2 C 0.7159(15) 0.1681(15) 0.6920(12) 0.031(3) Uani 1 1 d U . . H2 H 0.7444 0.2674 0.6820 0.037 Uiso 1 1 calc R . . C3 C 0.8437(14) 0.0994(15) 0.7689(11) 0.029(3) Uani 1 1 d U . . H3A H 0.8051 0.0144 0.8011 0.035 Uiso 1 1 calc R . . H3B H 0.8869 0.1628 0.8367 0.035 Uiso 1 1 calc R . . C4 C 0.9652(16) 0.0610(16) 0.7036(12) 0.038(4) Uani 1 1 d U . . H4A H 1.0084 0.1460 0.6751 0.045 Uiso 1 1 calc R . . H4B H 1.0459 0.0158 0.7582 0.045 Uiso 1 1 calc R . . C5 C 0.9036(14) -0.0359(14) 0.6001(11) 0.028(3) Uani 1 1 d U . . H5A H 0.8577 -0.1200 0.6279 0.033 Uiso 1 1 calc R . . H5B H 0.9852 -0.0647 0.5605 0.033 Uiso 1 1 calc R . . C6 C 0.7862(15) 0.0390(15) 0.5130(12) 0.033(3) Uani 1 1 d U . . H6A H 0.8359 0.1167 0.4793 0.040 Uiso 1 1 calc R . . H6B H 0.7415 -0.0263 0.4469 0.040 Uiso 1 1 calc R . . C7 C 0.6643(16) 0.0947(15) 0.5685(11) 0.034(3) Uani 1 1 d U . . H7 H 0.6086 0.1624 0.5136 0.040 Uiso 1 1 calc R . . C8 C 0.5503(14) -0.0151(14) 0.5974(11) 0.026(3) Uani 1 1 d U . . H8A H 0.4831 -0.0513 0.5240 0.031 Uiso 1 1 calc R . . H8B H 0.6023 -0.0936 0.6391 0.031 Uiso 1 1 calc R . . C9 C 0.4611(15) 0.0630(14) 0.6781(11) 0.029(3) Uani 1 1 d U . . C10 C 0.3904(13) -0.0266(12) 0.7576(10) 0.020(3) Uani 1 1 d U . . O10 O 0.3403(10) -0.1439(9) 0.7270(8) 0.029(2) Uani 1 1 d U . . N11 N 0.3874(10) 0.0314(10) 0.8656(8) 0.016(2) Uani 1 1 d U . . C12 C 0.3535(14) -0.0566(12) 0.9655(10) 0.021(3) Uani 1 1 d U . . H12 H 0.2502 -0.0996 0.9447 0.025 Uiso 1 1 calc R . . C13 C 0.4705(14) -0.1679(13) 0.9909(10) 0.023(3) Uani 1 1 d U . . H13A H 0.4478 -0.2422 0.9284 0.027 Uiso 1 1 calc R . . H13B H 0.5705 -0.1263 0.9890 0.027 Uiso 1 1 calc R . . C14 C 0.4726(15) -0.2301(14) 1.1110(11) 0.030(3) Uani 1 1 d U . . H14A H 0.5497 -0.3010 1.1256 0.036 Uiso 1 1 calc R . . H14B H 0.3743 -0.2760 1.1118 0.036 Uiso 1 1 calc R . . C15 C 0.5069(16) -0.1156(15) 1.2094(11) 0.036(4) Uani 1 1 d U . . H15A H 0.5061 -0.1569 1.2872 0.043 Uiso 1 1 calc R . . H15B H 0.6080 -0.0738 1.2117 0.043 Uiso 1 1 calc R . . C16 C 0.3937(16) -0.0047(16) 1.1882(13) 0.039(4) Uani 1 1 d U . . H16A H 0.4278 0.0734 1.2455 0.047 Uiso 1 1 calc R . . H16B H 0.2979 -0.0426 1.2044 0.047 Uiso 1 1 calc R . . C17 C 0.3655(15) 0.0510(14) 1.0644(10) 0.025(3) Uani 1 1 d U . . H17 H 0.2680 0.0983 1.0528 0.031 Uiso 1 1 calc R . . C18 C 0.4817(14) 0.1564(13) 1.0428(10) 0.024(3) Uani 1 1 d U . . H18A H 0.5838 0.1224 1.0690 0.029 Uiso 1 1 calc R . . H18B H 0.4734 0.2455 1.0853 0.029 Uiso 1 1 calc R . . C19 C 0.4455(14) 0.1735(13) 0.9069(11) 0.025(3) Uani 1 1 d U . . C20 C 0.5779(13) 0.2165(12) 0.8530(10) 0.021(3) Uani 1 1 d U . . O20 O 0.6767(11) 0.2945(10) 0.9041(8) 0.038(2) Uani 1 1 d U . . C21 C 0.2312(16) 0.0505(16) 0.4689(12) 0.040(4) Uani 1 1 d U . . H21A H 0.2994 0.0448 0.4132 0.059 Uiso 1 1 calc R . . H21B H 0.1355 0.0856 0.4285 0.059 Uiso 1 1 calc R . . H21C H 0.2148 -0.0420 0.4985 0.059 Uiso 1 1 calc R . . C22 C 0.3741(17) 0.4506(15) 0.9478(14) 0.045(4) Uani 1 1 d U . . H22A H 0.3810 0.4355 1.0326 0.068 Uiso 1 1 calc R . . H22B H 0.3105 0.5291 0.9243 0.068 Uiso 1 1 calc R . . H22C H 0.4743 0.4708 0.9323 0.068 Uiso 1 1 calc R . . S1' S 0.0592(4) 0.4434(4) 0.5255(3) 0.0334(9) Uani 1 1 d U . . S2' S -0.1133(4) 0.3086(3) 0.2506(3) 0.0288(8) Uani 1 1 d U . . N1' N 0.2367(11) 0.4496(11) 0.3617(9) 0.024(3) Uani 1 1 d U . . C2' C 0.3992(13) 0.4421(13) 0.4119(10) 0.025(3) Uani 1 1 d U . . H2' H 0.4236 0.3427 0.4255 0.030 Uiso 1 1 calc R . . C3' C 0.4955(14) 0.5012(15) 0.3327(12) 0.030(3) Uani 1 1 d U . . H3'1 H 0.4530 0.5883 0.2997 0.036 Uiso 1 1 calc R . . H3'2 H 0.4960 0.4349 0.2658 0.036 Uiso 1 1 calc R . . C4' C 0.6564(15) 0.5308(15) 0.3997(12) 0.032(3) Uani 1 1 d U . . H4'1 H 0.7007 0.4432 0.4299 0.039 Uiso 1 1 calc R . . H4'2 H 0.7171 0.5695 0.3449 0.039 Uiso 1 1 calc R . . C5' C 0.6591(16) 0.6323(16) 0.5017(12) 0.035(3) Uani 1 1 d U . . H5'1 H 0.7637 0.6537 0.5421 0.041 Uiso 1 1 calc R . . H5'2 H 0.6141 0.7198 0.4718 0.041 Uiso 1 1 calc R . . C6' C 0.5730(15) 0.5713(16) 0.5878(14) 0.039(4) Uani 1 1 d U . . H6'1 H 0.5677 0.6426 0.6500 0.046 Uiso 1 1 calc R . . H6'2 H 0.6289 0.4932 0.6267 0.046 Uiso 1 1 calc R . . C7' C 0.4112(14) 0.5178(14) 0.5323(11) 0.028(3) Uani 1 1 d U . . H7' H 0.3764 0.4524 0.5881 0.034 Uiso 1 1 calc R . . C8' C 0.2945(14) 0.6294(14) 0.5016(11) 0.029(3) Uani 1 1 d U . . H8'1 H 0.2702 0.6725 0.5741 0.035 Uiso 1 1 calc R . . H8'2 H 0.3301 0.7027 0.4540 0.035 Uiso 1 1 calc R . . C9' C 0.1610(14) 0.5483(13) 0.4304(11) 0.023(3) Uani 1 1 d U . . C10' C 0.0493(14) 0.6312(14) 0.3525(11) 0.026(3) Uani 1 1 d U . . O10' O 0.0204(9) 0.7467(9) 0.3855(7) 0.026(2) Uani 1 1 d U . . N11' N -0.0126(11) 0.5747(11) 0.2441(9) 0.026(3) Uani 1 1 d U . . C12' C -0.0955(13) 0.6603(13) 0.1476(10) 0.024(3) Uani 1 1 d U . . H12' H -0.1856 0.6990 0.1722 0.028 Uiso 1 1 calc R . . C13' C 0.0041(14) 0.7763(13) 0.1189(11) 0.025(3) Uani 1 1 d U . . H13C H 0.1043 0.7405 0.1178 0.030 Uiso 1 1 calc R . . H13D H 0.0155 0.8497 0.1819 0.030 Uiso 1 1 calc R . . C14' C -0.0576(16) 0.8394(14) -0.0010(11) 0.034(4) Uani 1 1 d U . . H14C H -0.1555 0.8803 0.0001 0.041 Uiso 1 1 calc R . . H14D H 0.0121 0.9136 -0.0177 0.041 Uiso 1 1 calc R . . C15' C -0.0752(16) 0.7242(15) -0.0958(12) 0.035(4) Uani 1 1 d U . . H15C H -0.1124 0.7636 -0.1743 0.042 Uiso 1 1 calc R . . H15D H 0.0239 0.6857 -0.0969 0.042 Uiso 1 1 calc R . . C16' C -0.1818(15) 0.6084(15) -0.0756(11) 0.029(3) Uani 1 1 d U . . H16C H -0.1819 0.5334 -0.1360 0.035 Uiso 1 1 calc R . . H16D H -0.2840 0.6441 -0.0877 0.035 Uiso 1 1 calc R . . C17' C -0.1442(14) 0.5464(14) 0.0483(10) 0.025(3) Uani 1 1 d U . . H17' H -0.2353 0.4954 0.0635 0.030 Uiso 1 1 calc R . . C18' C -0.0148(13) 0.4496(13) 0.0688(10) 0.021(3) Uani 1 1 d U . . H18C H -0.0440 0.3584 0.0281 0.026 Uiso 1 1 calc R . . H18D H 0.0720 0.4897 0.0398 0.026 Uiso 1 1 calc R . . C19' C 0.0215(15) 0.4355(14) 0.2017(11) 0.028(3) Uani 1 1 d U . . C20' C 0.1740(13) 0.3908(13) 0.2543(10) 0.020(3) Uani 1 1 d U . . O20' O 0.2414(10) 0.3125(9) 0.2020(7) 0.030(2) Uani 1 1 d U . . C21' C 0.0652(18) 0.5584(17) 0.6529(13) 0.045(4) Uani 1 1 d U . . H21D H 0.1658 0.5608 0.7023 0.067 Uiso 1 1 calc R . . H21E H -0.0073 0.5248 0.6992 0.067 Uiso 1 1 calc R . . H21F H 0.0403 0.6521 0.6263 0.067 Uiso 1 1 calc R . . C22' C -0.0787(16) 0.1528(15) 0.1743(13) 0.040(4) Uani 1 1 d U . . H22D H -0.1255 0.1570 0.0902 0.060 Uiso 1 1 calc R . . H22E H -0.1212 0.0728 0.2088 0.060 Uiso 1 1 calc R . . H22F H 0.0293 0.1432 0.1820 0.060 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 S1 0.0315(19) 0.036(2) 0.0305(19) 0.0055(16) 0.0038(15) 0.0024(16) S2 0.036(2) 0.031(2) 0.036(2) -0.0059(16) 0.0027(16) 0.0078(16) N1 0.024(5) 0.024(5) 0.016(5) -0.001(4) 0.005(4) 0.002(4) C2 0.032(6) 0.035(7) 0.030(6) 0.005(5) 0.013(5) 0.000(5) C3 0.031(6) 0.028(6) 0.028(6) -0.002(5) 0.004(5) 0.001(5) C4 0.034(7) 0.045(7) 0.036(6) 0.008(6) 0.012(6) 0.004(6) C5 0.029(6) 0.034(7) 0.029(6) -0.004(5) 0.027(5) -0.005(5) C6 0.039(7) 0.029(7) 0.036(6) -0.002(5) 0.020(6) -0.014(5) C7 0.039(7) 0.040(7) 0.024(6) 0.012(5) 0.012(5) 0.003(6) C8 0.022(6) 0.028(6) 0.025(6) -0.007(5) 0.000(5) 0.004(5) C9 0.031(6) 0.027(6) 0.027(6) 0.000(5) -0.001(5) 0.008(5) C10 0.026(6) 0.018(6) 0.016(5) 0.001(5) 0.006(5) 0.001(5) O10 0.034(5) 0.026(5) 0.028(5) -0.008(4) 0.009(4) -0.009(4) N11 0.020(5) 0.012(5) 0.016(5) -0.004(4) 0.006(4) 0.001(4) C12 0.030(6) 0.022(6) 0.010(5) -0.001(5) 0.004(5) -0.001(5) C13 0.030(6) 0.023(6) 0.018(5) 0.001(5) 0.010(5) 0.003(5) C14 0.031(6) 0.033(7) 0.027(6) 0.008(5) 0.005(5) 0.007(5) C15 0.045(7) 0.043(7) 0.022(6) -0.001(5) 0.013(6) -0.003(6) C16 0.035(7) 0.040(7) 0.039(7) -0.008(6) 0.002(6) -0.003(6) C17 0.032(6) 0.029(6) 0.018(5) -0.001(5) 0.013(5) -0.003(5) C18 0.030(6) 0.026(6) 0.020(6) -0.002(5) 0.011(5) -0.001(5) C19 0.028(6) 0.022(6) 0.023(6) 0.001(5) -0.004(5) 0.013(5) C20 0.020(6) 0.019(6) 0.026(6) 0.000(5) 0.007(5) -0.006(5) O20 0.039(5) 0.035(5) 0.037(5) -0.007(4) 0.006(4) -0.007(4) C21 0.038(7) 0.047(7) 0.032(6) 0.001(6) 0.000(6) 0.000(6) C22 0.041(7) 0.033(7) 0.058(8) -0.008(6) 0.006(6) -0.002(6) S1' 0.037(2) 0.040(2) 0.0258(18) -0.0021(16) 0.0121(16) 0.0058(17) S2' 0.0314(19) 0.0251(19) 0.0302(18) -0.0044(15) 0.0073(15) 0.0020(15) N1' 0.024(5) 0.021(5) 0.027(5) 0.002(4) 0.006(4) 0.004(4) C2' 0.028(6) 0.021(6) 0.022(6) -0.001(5) -0.004(5) 0.013(5) C3' 0.028(6) 0.031(7) 0.033(6) 0.009(5) 0.009(5) 0.003(5) C4' 0.030(6) 0.030(7) 0.037(6) 0.010(6) 0.008(5) 0.005(5) C5' 0.032(6) 0.034(7) 0.038(6) -0.002(6) 0.007(5) 0.000(6) C6' 0.037(7) 0.028(7) 0.049(7) 0.004(6) 0.004(6) 0.008(6) C7' 0.030(6) 0.033(6) 0.022(6) -0.001(5) 0.001(5) 0.011(5) C8' 0.027(6) 0.031(7) 0.026(6) -0.009(5) 0.000(5) 0.010(5) C9' 0.030(6) 0.016(6) 0.027(6) -0.004(5) 0.011(5) 0.010(5) C10' 0.024(6) 0.035(7) 0.020(6) -0.002(5) 0.006(5) 0.001(5) O10' 0.036(5) 0.023(5) 0.020(4) -0.014(4) 0.006(4) 0.010(4) N11' 0.024(5) 0.019(5) 0.034(6) -0.004(4) 0.005(4) 0.013(4) C12' 0.012(5) 0.031(6) 0.024(6) -0.005(5) -0.004(5) 0.004(5) C13' 0.025(6) 0.021(6) 0.026(6) -0.002(5) -0.001(5) 0.002(5) C14' 0.044(7) 0.027(6) 0.029(6) -0.003(5) 0.003(5) 0.002(6) C15' 0.044(7) 0.035(7) 0.028(6) 0.000(5) 0.007(5) 0.018(6) C16' 0.030(6) 0.036(7) 0.020(6) -0.006(5) 0.002(5) 0.005(5) C17' 0.020(6) 0.031(6) 0.019(6) 0.002(5) -0.003(5) -0.006(5) C18' 0.024(6) 0.026(6) 0.014(5) 0.004(5) 0.002(5) -0.002(5) C19' 0.037(6) 0.028(6) 0.023(6) -0.006(5) 0.010(5) 0.006(5) C20' 0.014(5) 0.023(6) 0.025(6) 0.001(5) 0.011(5) 0.000(5) O20' 0.034(5) 0.026(5) 0.030(4) -0.007(4) 0.009(4) 0.011(4) C21' 0.053(8) 0.050(8) 0.035(7) -0.008(6) 0.016(6) 0.004(6) C22' 0.045(7) 0.038(7) 0.040(7) 0.006(6) 0.013(6) 0.002(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C21 1.809(14) . ? S1 C9 1.854(13) . ? S2 C22 1.838(14) . ? S2 C19 1.844(12) . ? N1 C20 1.354(15) . ? N1 C9 1.484(16) . ? N1 C2 1.488(17) . ? C2 C3 1.501(18) . ? C2 C7 1.553(18) . ? C2 H2 1.0000 . ? C3 C4 1.507(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.503(18) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.529(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C7 1.494(19) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.549(18) . ? C7 H7 1.0000 . ? C8 C9 1.547(17) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.496(18) . ? C10 O10 1.225(14) . ? C10 N11 1.356(14) . ? N11 C19 1.486(15) . ? N11 C12 1.519(15) . ? C12 C17 1.507(16) . ? C12 C13 1.530(16) . ? C12 H12 1.0000 . ? C13 C14 1.517(16) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.542(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.501(19) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.513(19) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.506(17) . ? C17 H17 1.0000 . ? C18 C19 1.548(16) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.515(18) . ? C20 O20 1.205(14) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? S1' C21' 1.808(14) . ? S1' C9' 1.866(14) . ? S2' C22' 1.789(15) . ? S2' C19' 1.882(15) . ? N1' C20' 1.359(14) . ? N1' C2' 1.486(15) . ? N1' C9' 1.492(15) . ? C2' C3' 1.496(19) . ? C2' C7' 1.533(16) . ? C2' H2' 1.0000 . ? C3' C4' 1.533(17) . ? C3' H3'1 0.9900 . ? C3' H3'2 0.9900 . ? C4' C5' 1.506(19) . ? C4' H4'1 0.9900 . ? C4' H4'2 0.9900 . ? C5' C6' 1.50(2) . ? C5' H5'1 0.9900 . ? C5' H5'2 0.9900 . ? C6' C7' 1.556(18) . ? C6' H6'1 0.9900 . ? C6' H6'2 0.9900 . ? C7' C8' 1.537(17) . ? C7' H7' 1.0000 . ? C8' C9' 1.511(17) . ? C8' H8'1 0.9900 . ? C8' H8'2 0.9900 . ? C9' C10' 1.486(17) . ? C10' O10' 1.222(14) . ? C10' N11' 1.358(15) . ? N11' C19' 1.480(15) . ? N11' C12' 1.497(16) . ? C12' C13' 1.503(18) . ? C12' C17' 1.555(16) . ? C12' H12' 1.0000 . ? C13' C14' 1.533(17) . ? C13' H13C 0.9900 . ? C13' H13D 0.9900 . ? C14' C15' 1.521(17) . ? C14' H14C 0.9900 . ? C14' H14D 0.9900 . ? C15' C16' 1.511(19) . ? C15' H15C 0.9900 . ? C15' H15D 0.9900 . ? C16' C17' 1.541(17) . ? C16' H16C 0.9900 . ? C16' H16D 0.9900 . ? C17' C18' 1.514(17) . ? C17' H17' 1.0000 . ? C18' C19' 1.511(16) . ? C18' H18C 0.9900 . ? C18' H18D 0.9900 . ? C19' C20' 1.486(16) . ? C20' O20' 1.209(14) . ? C21' H21D 0.9800 . ? C21' H21E 0.9800 . ? C21' H21F 0.9800 . ? C22' H22D 0.9800 . ? C22' H22E 0.9800 . ? C22' H22F 0.9800 . ? 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 C21 S1 C9 102.8(6) . . ? C22 S2 C19 100.0(6) . . ? C20 N1 C9 124.2(11) . . ? C20 N1 C2 121.4(10) . . ? C9 N1 C2 113.3(10) . . ? N1 C2 C3 111.1(11) . . ? N1 C2 C7 103.2(10) . . ? C3 C2 C7 113.3(11) . . ? N1 C2 H2 109.7 . . ? C3 C2 H2 109.7 . . ? C7 C2 H2 109.7 . . ? C2 C3 C4 113.0(12) . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C5 C4 C3 110.5(11) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 108.8(11) . . ? C4 C5 H5A 109.9 . . ? C6 C5 H5A 109.9 . . ? C4 C5 H5B 109.9 . . ? C6 C5 H5B 109.9 . . ? H5A C5 H5B 108.3 . . ? C7 C6 C5 113.2(11) . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.8 . . ? C6 C7 C8 115.5(12) . . ? C6 C7 C2 115.6(11) . . ? C8 C7 C2 100.4(10) . . ? C6 C7 H7 108.2 . . ? C8 C7 H7 108.2 . . ? C2 C7 H7 108.2 . . ? C9 C8 C7 104.9(11) . . ? C9 C8 H8A 110.8 . . ? C7 C8 H8A 110.8 . . ? C9 C8 H8B 110.8 . . ? C7 C8 H8B 110.8 . . ? H8A C8 H8B 108.8 . . ? N1 C9 C10 112.9(10) . . ? N1 C9 C8 100.6(10) . . ? C10 C9 C8 115.2(11) . . ? N1 C9 S1 108.1(8) . . ? C10 C9 S1 107.6(9) . . ? C8 C9 S1 112.1(9) . . ? O10 C10 N11 122.9(12) . . ? O10 C10 C9 122.1(11) . . ? N11 C10 C9 115.0(10) . . ? C10 N11 C19 125.1(11) . . ? C10 N11 C12 120.9(9) . . ? C19 N11 C12 112.8(9) . . ? C17 C12 N11 101.2(9) . . ? C17 C12 C13 113.4(10) . . ? N11 C12 C13 108.8(10) . . ? C17 C12 H12 111.0 . . ? N11 C12 H12 111.0 . . ? C13 C12 H12 111.0 . . ? C14 C13 C12 111.2(10) . . ? C14 C13 H13A 109.4 . . ? C12 C13 H13A 109.4 . . ? C14 C13 H13B 109.4 . . ? C12 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C13 C14 C15 110.1(11) . . ? C13 C14 H14A 109.6 . . ? C15 C14 H14A 109.6 . . ? C13 C14 H14B 109.6 . . ? C15 C14 H14B 109.6 . . ? H14A C14 H14B 108.1 . . ? C16 C15 C14 110.9(11) . . ? C16 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? C16 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 114.9(13) . . ? C15 C16 H16A 108.5 . . ? C17 C16 H16A 108.5 . . ? C15 C16 H16B 108.5 . . ? C17 C16 H16B 108.5 . . ? H16A C16 H16B 107.5 . . ? C12 C17 C18 105.3(10) . . ? C12 C17 C16 115.4(11) . . ? C18 C17 C16 114.4(10) . . ? C12 C17 H17 107.1 . . ? C18 C17 H17 107.1 . . ? C16 C17 H17 107.1 . . ? C17 C18 C19 103.9(10) . . ? C17 C18 H18A 111.0 . . ? C19 C18 H18A 111.0 . . ? C17 C18 H18B 111.0 . . ? C19 C18 H18B 111.0 . . ? H18A C18 H18B 109.0 . . ? N11 C19 C20 111.5(10) . . ? N11 C19 C18 101.0(10) . . ? C20 C19 C18 114.9(10) . . ? N11 C19 S2 107.8(8) . . ? C20 C19 S2 109.5(8) . . ? C18 C19 S2 111.8(9) . . ? O20 C20 N1 122.1(12) . . ? O20 C20 C19 122.2(11) . . ? N1 C20 C19 115.7(10) . . ? S1 C21 H21A 109.5 . . ? S1 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? S1 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? S2 C22 H22A 109.5 . . ? S2 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? S2 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21' S1' C9' 102.5(7) . . ? C22' S2' C19' 101.3(6) . . ? C20' N1' C2' 121.9(10) . . ? C20' N1' C9' 124.8(9) . . ? C2' N1' C9' 112.4(9) . . ? N1' C2' C3' 112.9(10) . . ? N1' C2' C7' 101.5(10) . . ? C3' C2' C7' 115.7(11) . . ? N1' C2' H2' 108.8 . . ? C3' C2' H2' 108.8 . . ? C7' C2' H2' 108.8 . . ? C2' C3' C4' 111.6(11) . . ? C2' C3' H3'1 109.3 . . ? C4' C3' H3'1 109.3 . . ? C2' C3' H3'2 109.3 . . ? C4' C3' H3'2 109.3 . . ? H3'1 C3' H3'2 108.0 . . ? C5' C4' C3' 110.5(12) . . ? C5' C4' H4'1 109.6 . . ? C3' C4' H4'1 109.6 . . ? C5' C4' H4'2 109.6 . . ? C3' C4' H4'2 109.6 . . ? H4'1 C4' H4'2 108.1 . . ? C6' C5' C4' 109.7(12) . . ? C6' C5' H5'1 109.7 . . ? C4' C5' H5'1 109.7 . . ? C6' C5' H5'2 109.7 . . ? C4' C5' H5'2 109.7 . . ? H5'1 C5' H5'2 108.2 . . ? C5' C6' C7' 114.9(12) . . ? C5' C6' H6'1 108.5 . . ? C7' C6' H6'1 108.5 . . ? C5' C6' H6'2 108.5 . . ? C7' C6' H6'2 108.5 . . ? H6'1 C6' H6'2 107.5 . . ? C2' C7' C8' 101.4(9) . . ? C2' C7' C6' 113.3(12) . . ? C8' C7' C6' 116.1(11) . . ? C2' C7' H7' 108.5 . . ? C8' C7' H7' 108.5 . . ? C6' C7' H7' 108.5 . . ? C9' C8' C7' 102.9(10) . . ? C9' C8' H8'1 111.2 . . ? C7' C8' H8'1 111.2 . . ? C9' C8' H8'2 111.2 . . ? C7' C8' H8'2 111.2 . . ? H8'1 C8' H8'2 109.1 . . ? C10' C9' N1' 112.4(10) . . ? C10' C9' C8' 115.8(11) . . ? N1' C9' C8' 100.7(9) . . ? C10' C9' S1' 107.6(9) . . ? N1' C9' S1' 107.5(8) . . ? C8' C9' S1' 112.5(9) . . ? O10' C10' N11' 122.8(11) . . ? O10' C10' C9' 120.0(10) . . ? N11' C10' C9' 117.1(11) . . ? C10' N11' C19' 123.9(10) . . ? C10' N11' C12' 121.7(10) . . ? C19' N11' C12' 113.2(10) . . ? N11' C12' C13' 110.6(9) . . ? N11' C12' C17' 100.1(10) . . ? C13' C12' C17' 115.6(11) . . ? N11' C12' H12' 110.0 . . ? C13' C12' H12' 110.0 . . ? C17' C12' H12' 110.0 . . ? C12' C13' C14' 112.5(10) . . ? C12' C13' H13C 109.1 . . ? C14' C13' H13C 109.1 . . ? C12' C13' H13D 109.1 . . ? C14' C13' H13D 109.1 . . ? H13C C13' H13D 107.8 . . ? C15' C14' C13' 107.9(11) . . ? C15' C14' H14C 110.1 . . ? C13' C14' H14C 110.1 . . ? C15' C14' H14D 110.1 . . ? C13' C14' H14D 110.1 . . ? H14C C14' H14D 108.4 . . ? C16' C15' C14' 112.5(12) . . ? C16' C15' H15C 109.1 . . ? C14' C15' H15C 109.1 . . ? C16' C15' H15D 109.1 . . ? C14' C15' H15D 109.1 . . ? H15C C15' H15D 107.8 . . ? C15' C16' C17' 114.4(10) . . ? C15' C16' H16C 108.7 . . ? C17' C16' H16C 108.7 . . ? C15' C16' H16D 108.7 . . ? C17' C16' H16D 108.7 . . ? H16C C16' H16D 107.6 . . ? C18' C17' C16' 116.0(11) . . ? C18' C17' C12' 102.8(9) . . ? C16' C17' C12' 112.0(11) . . ? C18' C17' H17' 108.6 . . ? C16' C17' H17' 108.6 . . ? C12' C17' H17' 108.6 . . ? C19' C18' C17' 104.2(10) . . ? C19' C18' H18C 110.9 . . ? C17' C18' H18C 110.9 . . ? C19' C18' H18D 110.9 . . ? C17' C18' H18D 110.9 . . ? H18C C18' H18D 108.9 . . ? N11' C19' C20' 113.9(10) . . ? N11' C19' C18' 101.8(10) . . ? C20' C19' C18' 117.0(11) . . ? N11' C19' S2' 106.7(9) . . ? C20' C19' S2' 106.4(9) . . ? C18' C19' S2' 110.8(9) . . ? O20' C20' N1' 121.9(11) . . ? O20' C20' C19' 122.1(11) . . ? N1' C20' C19' 115.9(10) . . ? S1' C21' H21D 109.5 . . ? S1' C21' H21E 109.5 . . ? H21D C21' H21E 109.5 . . ? S1' C21' H21F 109.5 . . ? H21D C21' H21F 109.5 . . ? H21E C21' H21F 109.5 . . ? S2' C22' H22D 109.5 . . ? S2' C22' H22E 109.5 . . ? H22D C22' H22E 109.5 . . ? S2' C22' H22F 109.5 . . ? H22D C22' H22F 109.5 . . ? H22E C22' H22F 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 C20 N1 C2 C3 59.5(16) . . . . ? C9 N1 C2 C3 -108.6(12) . . . . ? C20 N1 C2 C7 -178.7(11) . . . . ? C9 N1 C2 C7 13.2(13) . . . . ? N1 C2 C3 C4 160.5(11) . . . . ? C7 C2 C3 C4 44.8(17) . . . . ? C2 C3 C4 C5 -58.9(16) . . . . ? C3 C4 C5 C6 62.8(15) . . . . ? C4 C5 C6 C7 -55.5(15) . . . . ? C5 C6 C7 C8 -73.3(15) . . . . ? C5 C6 C7 C2 43.5(17) . . . . ? N1 C2 C7 C6 -158.1(12) . . . . ? C3 C2 C7 C6 -37.8(17) . . . . ? N1 C2 C7 C8 -33.0(12) . . . . ? C3 C2 C7 C8 87.3(13) . . . . ? C6 C7 C8 C9 167.4(11) . . . . ? C2 C7 C8 C9 42.3(12) . . . . ? C20 N1 C9 C10 -31.6(16) . . . . ? C2 N1 C9 C10 136.1(11) . . . . ? C20 N1 C9 C8 -155.0(11) . . . . ? C2 N1 C9 C8 12.8(13) . . . . ? C20 N1 C9 S1 87.3(12) . . . . ? C2 N1 C9 S1 -104.9(10) . . . . ? C7 C8 C9 N1 -34.0(11) . . . . ? C7 C8 C9 C10 -155.8(10) . . . . ? C7 C8 C9 S1 80.7(11) . . . . ? C21 S1 C9 N1 153.2(9) . . . . ? C21 S1 C9 C10 -84.5(10) . . . . ? C21 S1 C9 C8 43.2(11) . . . . ? N1 C9 C10 O10 -149.6(11) . . . . ? C8 C9 C10 O10 -34.8(16) . . . . ? S1 C9 C10 O10 91.1(13) . . . . ? N1 C9 C10 N11 29.8(15) . . . . ? C8 C9 C10 N11 144.6(10) . . . . ? S1 C9 C10 N11 -89.5(10) . . . . ? O10 C10 N11 C19 -179.5(11) . . . . ? C9 C10 N11 C19 1.1(16) . . . . ? O10 C10 N11 C12 13.9(17) . . . . ? C9 C10 N11 C12 -165.5(10) . . . . ? C10 N11 C12 C17 179.1(10) . . . . ? C19 N11 C12 C17 11.0(12) . . . . ? C10 N11 C12 C13 59.4(13) . . . . ? C19 N11 C12 C13 -108.7(11) . . . . ? C17 C12 C13 C14 51.0(15) . . . . ? N11 C12 C13 C14 162.8(9) . . . . ? C12 C13 C14 C15 -58.7(14) . . . . ? C13 C14 C15 C16 58.0(16) . . . . ? C14 C15 C16 C17 -49.7(17) . . . . ? N11 C12 C17 C18 -31.6(12) . . . . ? C13 C12 C17 C18 84.7(13) . . . . ? N11 C12 C17 C16 -158.7(11) . . . . ? C13 C12 C17 C16 -42.4(16) . . . . ? C15 C16 C17 C12 42.5(17) . . . . ? C15 C16 C17 C18 -79.8(15) . . . . ? C12 C17 C18 C19 41.3(12) . . . . ? C16 C17 C18 C19 169.0(12) . . . . ? C10 N11 C19 C20 -31.9(15) . . . . ? C12 N11 C19 C20 135.7(10) . . . . ? C10 N11 C19 C18 -154.4(11) . . . . ? C12 N11 C19 C18 13.2(12) . . . . ? C10 N11 C19 S2 88.3(12) . . . . ? C12 N11 C19 S2 -104.2(9) . . . . ? C17 C18 C19 N11 -32.4(12) . . . . ? C17 C18 C19 C20 -152.5(10) . . . . ? C17 C18 C19 S2 81.9(11) . . . . ? C22 S2 C19 N11 168.4(9) . . . . ? C22 S2 C19 C20 -70.1(10) . . . . ? C22 S2 C19 C18 58.4(11) . . . . ? C9 N1 C20 O20 179.5(11) . . . . ? C2 N1 C20 O20 12.7(18) . . . . ? C9 N1 C20 C19 0.3(16) . . . . ? C2 N1 C20 C19 -166.5(11) . . . . ? N11 C19 C20 O20 -149.4(12) . . . . ? C18 C19 C20 O20 -35.4(17) . . . . ? S2 C19 C20 O20 91.4(13) . . . . ? N11 C19 C20 N1 29.8(14) . . . . ? C18 C19 C20 N1 143.9(11) . . . . ? S2 C19 C20 N1 -89.3(11) . . . . ? C20' N1' C2' C3' 57.3(15) . . . . ? C9' N1' C2' C3' -112.2(12) . . . . ? C20' N1' C2' C7' -178.2(11) . . . . ? C9' N1' C2' C7' 12.3(13) . . . . ? N1' C2' C3' C4' 163.5(10) . . . . ? C7' C2' C3' C4' 47.2(15) . . . . ? C2' C3' C4' C5' -59.4(15) . . . . ? C3' C4' C5' C6' 61.8(15) . . . . ? C4' C5' C6' C7' -52.9(16) . . . . ? N1' C2' C7' C8' -35.0(13) . . . . ? C3' C2' C7' C8' 87.6(13) . . . . ? N1' C2' C7' C6' -160.2(11) . . . . ? C3' C2' C7' C6' -37.6(15) . . . . ? C5' C6' C7' C2' 40.6(17) . . . . ? C5' C6' C7' C8' -76.3(16) . . . . ? C2' C7' C8' C9' 46.6(13) . . . . ? C6' C7' C8' C9' 169.8(12) . . . . ? C20' N1' C9' C10' -29.3(17) . . . . ? C2' N1' C9' C10' 139.8(11) . . . . ? C20' N1' C9' C8' -153.1(12) . . . . ? C2' N1' C9' C8' 16.0(13) . . . . ? C20' N1' C9' S1' 89.0(12) . . . . ? C2' N1' C9' S1' -101.9(10) . . . . ? C7' C8' C9' C10' -159.3(11) . . . . ? C7' C8' C9' N1' -37.8(12) . . . . ? C7' C8' C9' S1' 76.4(11) . . . . ? C21' S1' C9' C10' -89.4(9) . . . . ? C21' S1' C9' N1' 149.2(8) . . . . ? C21' S1' C9' C8' 39.3(10) . . . . ? N1' C9' C10' O10' -152.0(12) . . . . ? C8' C9' C10' O10' -37.1(18) . . . . ? S1' C9' C10' O10' 89.7(13) . . . . ? N1' C9' C10' N11' 25.6(17) . . . . ? C8' C9' C10' N11' 140.6(12) . . . . ? S1' C9' C10' N11' -92.6(12) . . . . ? O10' C10' N11' C19' 179.5(13) . . . . ? C9' C10' N11' C19' 2(2) . . . . ? O10' C10' N11' C12' 13(2) . . . . ? C9' C10' N11' C12' -164.5(11) . . . . ? C10' N11' C12' C13' 59.1(16) . . . . ? C19' N11' C12' C13' -108.7(12) . . . . ? C10' N11' C12' C17' -178.5(11) . . . . ? C19' N11' C12' C17' 13.8(13) . . . . ? N11' C12' C13' C14' 163.0(10) . . . . ? C17' C12' C13' C14' 50.1(15) . . . . ? C12' C13' C14' C15' -58.3(15) . . . . ? C13' C14' C15' C16' 60.3(15) . . . . ? C14' C15' C16' C17' -53.7(16) . . . . ? C15' C16' C17' C18' -76.2(15) . . . . ? C15' C16' C17' C12' 41.5(15) . . . . ? N11' C12' C17' C18' -33.9(12) . . . . ? C13' C12' C17' C18' 85.0(12) . . . . ? N11' C12' C17' C16' -159.1(10) . . . . ? C13' C12' C17' C16' -40.3(14) . . . . ? C16' C17' C18' C19' 165.8(11) . . . . ? C12' C17' C18' C19' 43.2(13) . . . . ? C10' N11' C19' C20' -28.8(19) . . . . ? C12' N11' C19' C20' 138.7(11) . . . . ? C10' N11' C19' C18' -155.5(12) . . . . ? C12' N11' C19' C18' 11.9(14) . . . . ? C10' N11' C19' S2' 88.3(13) . . . . ? C12' N11' C19' S2' -104.3(10) . . . . ? C17' C18' C19' N11' -33.6(13) . . . . ? C17' C18' C19' C20' -158.4(11) . . . . ? C17' C18' C19' S2' 79.5(11) . . . . ? C22' S2' C19' N11' 171.3(8) . . . . ? C22' S2' C19' C20' -66.8(9) . . . . ? C22' S2' C19' C18' 61.3(10) . . . . ? C2' N1' C20' O20' 11.1(18) . . . . ? C9' N1' C20' O20' 179.2(12) . . . . ? C2' N1' C20' C19' -165.1(11) . . . . ? C9' N1' C20' C19' 3.0(18) . . . . ? N11' C19' C20' O20' -151.0(12) . . . . ? C18' C19' C20' O20' -32.6(19) . . . . ? S2' C19' C20' O20' 91.8(13) . . . . ? N11' C19' C20' N1' 25.1(16) . . . . ? C18' C19' C20' N1' 143.5(12) . . . . ? S2' C19' C20' N1' -92.1(11) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C7' H7' S1 1.00 2.80 3.593(15) 136.6 . C8' H8'1 O10 0.99 2.44 3.305(15) 145.1 1_565 _diffrn_measured_fraction_theta_max 0.888 _diffrn_reflns_theta_full 24.96 _diffrn_measured_fraction_theta_full 0.888 _refine_diff_density_max 0.665 _refine_diff_density_min -0.447 _refine_diff_density_rms 0.112 # start Validation Reply Form _vrf_PLAT029_sb344 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.888 RESPONSE: data collection startgy was tuned to the point group and space group P-1, but due to the unusual space groue P1 no completeness of data ; # end Validation Reply Form #============================================================================== data_sb346_hy _database_code_depnum_ccdc_archive 'CCDC 852473' #TrackingRef 'obc_bmr_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5a,10a-bis(methylthio)octahydrodipyrrolo[1,2-a:1',2'-d]pyrazine-5,10-dione ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H18 N2 O2 S2' _chemical_formula_sum 'C12 H18 N2 O2 S2' _chemical_formula_weight 286.40 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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 17.1844(13) _cell_length_b 7.3729(5) _cell_length_c 10.8107(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.732(3) _cell_angle_gamma 90.00 _cell_volume 1318.39(17) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 1431 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description rods _exptl_crystal_colour colourless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.400 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 20 sec./deg., 2 deg., 2 sets, 98 frames ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius APEXII' _diffrn_measurement_method 'rotation in phi and omega, 2 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6338 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0401 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.02 _diffrn_reflns_theta_max 27.45 _reflns_number_total 2966 _reflns_number_gt 2563 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMN _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0111P)^2^+2.4621P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2966 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0481 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.138 _refine_ls_restrained_S_all 1.138 _refine_ls_shift/su_max 0.000 _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 S1 S 0.17191(4) 0.56720(9) 0.77254(6) 0.02205(16) Uani 1 1 d . . . S2 S 0.38072(4) 0.49596(9) 0.74631(6) 0.02161(15) Uani 1 1 d . . . N1 N 0.22361(12) 0.8023(3) 0.62428(19) 0.0167(4) Uani 1 1 d . . . C2 C 0.18617(15) 0.9810(4) 0.6286(3) 0.0261(6) Uani 1 1 d . . . H2A H 0.1913 1.0584 0.5563 0.031 Uiso 1 1 calc R . . H2B H 0.2114 1.0439 0.7106 0.031 Uiso 1 1 calc R . . C3 C 0.09783(15) 0.9369(4) 0.6171(3) 0.0249(6) Uani 1 1 d . . . H3A H 0.0616 1.0299 0.5656 0.030 Uiso 1 1 calc R . . H3B H 0.0878 0.9289 0.7029 0.030 Uiso 1 1 calc R . . C4 C 0.08509(14) 0.7520(3) 0.5489(2) 0.0198(5) Uani 1 1 d . . . H4A H 0.0391 0.6858 0.5665 0.024 Uiso 1 1 calc R . . H4B H 0.0754 0.7660 0.4549 0.024 Uiso 1 1 calc R . . C5 C 0.16526(14) 0.6552(3) 0.6087(2) 0.0163(5) Uani 1 1 d . . . C6 C 0.18329(14) 0.4971(3) 0.5308(2) 0.0164(5) Uani 1 1 d . . . O6 O 0.12896(10) 0.3938(2) 0.47422(17) 0.0236(4) Uani 1 1 d . . . N7 N 0.26126(11) 0.4763(3) 0.53133(19) 0.0161(4) Uani 1 1 d . . . C8 C 0.28990(15) 0.3284(4) 0.4627(3) 0.0224(5) Uani 1 1 d . . . H8A H 0.2499 0.3016 0.3798 0.027 Uiso 1 1 calc R . . H8B H 0.3000 0.2165 0.5153 0.027 Uiso 1 1 calc R . . C9 C 0.36899(16) 0.4023(4) 0.4409(3) 0.0243(6) Uani 1 1 d . . . H9A H 0.4157 0.3289 0.4887 0.029 Uiso 1 1 calc R . . H9B H 0.3667 0.3997 0.3484 0.029 Uiso 1 1 calc R . . C10 C 0.37646(15) 0.5978(4) 0.4909(2) 0.0221(5) Uani 1 1 d . . . H10A H 0.4337 0.6296 0.5316 0.027 Uiso 1 1 calc R . . H10B H 0.3538 0.6845 0.4204 0.027 Uiso 1 1 calc R . . C11 C 0.32728(14) 0.5993(3) 0.5898(2) 0.0169(5) Uani 1 1 d . . . C12 C 0.29995(14) 0.7873(3) 0.6141(2) 0.0168(5) Uani 1 1 d . . . O12 O 0.34552(10) 0.9179(2) 0.62436(18) 0.0241(4) Uani 1 1 d . . . C13 C 0.08180(16) 0.4305(4) 0.7449(3) 0.0287(6) Uani 1 1 d . . . H13A H 0.0343 0.5096 0.7288 0.043 Uiso 1 1 calc R . . H13B H 0.0845 0.3554 0.8208 0.043 Uiso 1 1 calc R . . H13C H 0.0777 0.3521 0.6702 0.043 Uiso 1 1 calc R . . C14 C 0.47333(15) 0.6238(4) 0.7928(3) 0.0300(6) Uani 1 1 d . . . H14A H 0.5061 0.5969 0.7337 0.045 Uiso 1 1 calc R . . H14B H 0.5034 0.5903 0.8805 0.045 Uiso 1 1 calc R . . H14C H 0.4608 0.7537 0.7896 0.045 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 S1 0.0216(3) 0.0284(3) 0.0169(3) 0.0036(3) 0.0064(2) 0.0000(3) S2 0.0195(3) 0.0210(3) 0.0222(3) 0.0028(2) 0.0019(2) 0.0015(2) N1 0.0156(9) 0.0127(10) 0.0216(10) -0.0013(8) 0.0045(8) 0.0003(8) C2 0.0212(12) 0.0163(13) 0.0391(15) -0.0080(11) 0.0051(11) 0.0020(10) C3 0.0187(12) 0.0232(13) 0.0312(14) -0.0040(11) 0.0041(10) 0.0053(10) C4 0.0138(11) 0.0220(12) 0.0232(12) 0.0002(10) 0.0044(9) 0.0003(10) C5 0.0148(11) 0.0180(12) 0.0161(11) -0.0004(9) 0.0044(9) -0.0014(9) C6 0.0193(11) 0.0148(11) 0.0148(11) 0.0008(9) 0.0041(9) -0.0005(9) O6 0.0204(9) 0.0221(9) 0.0273(10) -0.0059(8) 0.0044(7) -0.0054(7) N7 0.0164(9) 0.0149(10) 0.0166(9) -0.0019(8) 0.0038(7) -0.0009(8) C8 0.0264(13) 0.0188(12) 0.0247(13) -0.0027(10) 0.0114(10) 0.0018(10) C9 0.0257(13) 0.0245(14) 0.0258(13) -0.0001(11) 0.0121(11) 0.0043(11) C10 0.0224(12) 0.0223(13) 0.0254(13) 0.0045(10) 0.0128(10) -0.0018(10) C11 0.0130(10) 0.0163(12) 0.0211(12) 0.0020(9) 0.0045(9) -0.0002(9) C12 0.0151(11) 0.0163(11) 0.0179(11) 0.0005(9) 0.0025(9) 0.0002(9) O12 0.0168(8) 0.0157(9) 0.0388(11) -0.0007(8) 0.0058(8) -0.0031(7) C13 0.0239(13) 0.0322(15) 0.0320(15) 0.0088(12) 0.0109(11) -0.0038(12) C14 0.0181(12) 0.0336(16) 0.0342(15) -0.0049(13) 0.0000(11) 0.0014(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C13 1.803(3) . ? S1 C5 1.861(2) . ? S2 C14 1.800(3) . ? S2 C11 1.856(2) . ? N1 C12 1.350(3) . ? N1 C5 1.455(3) . ? N1 C2 1.473(3) . ? C2 C3 1.524(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.537(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.530(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.518(3) . ? C6 O6 1.231(3) . ? C6 N7 1.347(3) . ? N7 C11 1.456(3) . ? N7 C8 1.476(3) . ? C8 C9 1.541(4) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C10 1.533(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 C11 1.532(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.509(3) . ? C12 O12 1.227(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? 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 C13 S1 C5 102.06(12) . . ? C14 S2 C11 102.78(12) . . ? C12 N1 C5 125.7(2) . . ? C12 N1 C2 121.2(2) . . ? C5 N1 C2 112.16(18) . . ? N1 C2 C3 103.9(2) . . ? N1 C2 H2A 111.0 . . ? C3 C2 H2A 111.0 . . ? N1 C2 H2B 111.0 . . ? C3 C2 H2B 111.0 . . ? H2A C2 H2B 109.0 . . ? C2 C3 C4 103.7(2) . . ? C2 C3 H3A 111.0 . . ? C4 C3 H3A 111.0 . . ? C2 C3 H3B 111.0 . . ? C4 C3 H3B 111.0 . . ? H3A C3 H3B 109.0 . . ? C5 C4 C3 102.49(19) . . ? C5 C4 H4A 111.3 . . ? C3 C4 H4A 111.3 . . ? C5 C4 H4B 111.3 . . ? C3 C4 H4B 111.3 . . ? H4A C4 H4B 109.2 . . ? N1 C5 C6 113.50(19) . . ? N1 C5 C4 102.40(19) . . ? C6 C5 C4 114.8(2) . . ? N1 C5 S1 106.67(16) . . ? C6 C5 S1 106.90(16) . . ? C4 C5 S1 112.35(16) . . ? O6 C6 N7 123.4(2) . . ? O6 C6 C5 120.6(2) . . ? N7 C6 C5 115.9(2) . . ? C6 N7 C11 126.0(2) . . ? C6 N7 C8 123.3(2) . . ? C11 N7 C8 110.58(19) . . ? N7 C8 C9 104.1(2) . . ? N7 C8 H8A 110.9 . . ? C9 C8 H8A 110.9 . . ? N7 C8 H8B 110.9 . . ? C9 C8 H8B 110.9 . . ? H8A C8 H8B 109.0 . . ? C10 C9 C8 105.8(2) . . ? C10 C9 H9A 110.6 . . ? C8 C9 H9A 110.6 . . ? C10 C9 H9B 110.6 . . ? C8 C9 H9B 110.6 . . ? H9A C9 H9B 108.7 . . ? C11 C10 C9 104.1(2) . . ? C11 C10 H10A 110.9 . . ? C9 C10 H10A 110.9 . . ? C11 C10 H10B 110.9 . . ? C9 C10 H10B 110.9 . . ? H10A C10 H10B 109.0 . . ? N7 C11 C12 113.89(19) . . ? N7 C11 C10 101.83(19) . . ? C12 C11 C10 112.6(2) . . ? N7 C11 S2 105.95(16) . . ? C12 C11 S2 108.59(16) . . ? C10 C11 S2 113.77(17) . . ? O12 C12 N1 122.6(2) . . ? O12 C12 C11 121.0(2) . . ? N1 C12 C11 116.4(2) . . ? S1 C13 H13A 109.5 . . ? S1 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? S1 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? S2 C14 H14A 109.5 . . ? S2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? S2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 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 C12 N1 C2 C3 170.8(2) . . . . ? C5 N1 C2 C3 1.2(3) . . . . ? N1 C2 C3 C4 -24.3(3) . . . . ? C2 C3 C4 C5 37.9(3) . . . . ? C12 N1 C5 C6 -22.2(3) . . . . ? C2 N1 C5 C6 146.8(2) . . . . ? C12 N1 C5 C4 -146.6(2) . . . . ? C2 N1 C5 C4 22.5(3) . . . . ? C12 N1 C5 S1 95.3(2) . . . . ? C2 N1 C5 S1 -95.7(2) . . . . ? C3 C4 C5 N1 -36.5(2) . . . . ? C3 C4 C5 C6 -159.9(2) . . . . ? C3 C4 C5 S1 77.6(2) . . . . ? C13 S1 C5 N1 166.12(16) . . . . ? C13 S1 C5 C6 -72.14(18) . . . . ? C13 S1 C5 C4 54.7(2) . . . . ? N1 C5 C6 O6 -156.0(2) . . . . ? C4 C5 C6 O6 -38.7(3) . . . . ? S1 C5 C6 O6 86.7(2) . . . . ? N1 C5 C6 N7 25.7(3) . . . . ? C4 C5 C6 N7 143.0(2) . . . . ? S1 C5 C6 N7 -91.7(2) . . . . ? O6 C6 N7 C11 176.1(2) . . . . ? C5 C6 N7 C11 -5.6(3) . . . . ? O6 C6 N7 C8 0.8(4) . . . . ? C5 C6 N7 C8 179.0(2) . . . . ? C6 N7 C8 C9 156.4(2) . . . . ? C11 N7 C8 C9 -19.6(3) . . . . ? N7 C8 C9 C10 -4.3(3) . . . . ? C8 C9 C10 C11 24.9(3) . . . . ? C6 N7 C11 C12 -19.3(3) . . . . ? C8 N7 C11 C12 156.6(2) . . . . ? C6 N7 C11 C10 -140.8(2) . . . . ? C8 N7 C11 C10 35.1(2) . . . . ? C6 N7 C11 S2 100.0(2) . . . . ? C8 N7 C11 S2 -84.2(2) . . . . ? C9 C10 C11 N7 -35.8(2) . . . . ? C9 C10 C11 C12 -158.2(2) . . . . ? C9 C10 C11 S2 77.7(2) . . . . ? C14 S2 C11 N7 166.66(16) . . . . ? C14 S2 C11 C12 -70.62(18) . . . . ? C14 S2 C11 C10 55.6(2) . . . . ? C5 N1 C12 O12 177.6(2) . . . . ? C2 N1 C12 O12 9.5(4) . . . . ? C5 N1 C12 C11 -2.7(3) . . . . ? C2 N1 C12 C11 -170.8(2) . . . . ? N7 C11 C12 O12 -157.2(2) . . . . ? C10 C11 C12 O12 -41.9(3) . . . . ? S2 C11 C12 O12 85.0(2) . . . . ? N7 C11 C12 N1 23.1(3) . . . . ? C10 C11 C12 N1 138.4(2) . . . . ? S2 C11 C12 N1 -94.7(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8 H8B O12 0.99 2.52 3.496(3) 168.7 1_545 C13 H13B O6 0.98 2.45 3.381(3) 157.5 4_566 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.394 _refine_diff_density_min -0.288 _refine_diff_density_rms 0.070 #============================================================================== data_sb348_hy _database_code_depnum_ccdc_archive 'CCDC 852474' #TrackingRef 'obc_bmr_2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,7-bis(benzyloxy)tetrahydro-5a,10a-epidithiodipyrrolo[1,2-a:1',2'-d]- pyrazine-5,10(1H,6H)-dione and 2,7-bis(benzyloxy)tetrahydro-5a,10a-epitrithiodipyrrolo[1,2-a:1',2'-d]- pyrazine-5,10(1H,6H)-dione in the ration 2.69:0.31 ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ; 2.69(C24 H24 N2 O4 S2), 0.31(C24 H24 N2 O4 S2), 2(C H Cl3) ; _chemical_formula_sum 'C74 H74 Cl6 N6 O12 S6.31' _chemical_formula_weight 1654.39 _chemical_absolute_configuration ad 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' Cl Cl 0.1484 0.1585 '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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.4283(1) _cell_length_b 17.1077(2) _cell_length_c 19.3984(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.773(1) _cell_angle_gamma 90.00 _cell_volume 3788.18(7) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used 8876 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27.5 _exptl_crystal_description rods _exptl_crystal_colour 'pal yellow' _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.450 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1718 _exptl_absorpt_coefficient_mu 0.466 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; dx = 35 mm, 80 sec./deg., 1 deg., 7 sets, 530 frames ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius APEXII' _diffrn_measurement_method 'rotation in phi and omega, 1 deg.' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 51084 _diffrn_reflns_av_R_equivalents 0.0424 _diffrn_reflns_av_sigmaI/netI 0.0346 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.94 _diffrn_reflns_theta_max 27.48 _reflns_number_total 17215 _reflns_number_gt 15922 _reflns_threshold_expression >2sigma(I) _computing_data_collection Collect _computing_cell_refinement DENZO-SMN _computing_data_reduction DENZO-SMn _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Determination of absolute structure using Bayesian statistics on Bijvoet differences (Hooft, Straver and Spek, 2008): FLEQ = 0.047(13) (Platon: Spek, 2003). Both solvent molecules are disorderd. One of the three independent molecules is disorder in the S(n)-bridge. It's a disorder between a S(2) and S(3) bridge in the ration 0.69:0.31. Use of constraint (EADP) and restraints (SIMU)for the displacement parameters, and restraints (SAFDI) for 1,2- and 1,3-distances. ; _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^)+(0.0720P)^2^+11.2500P] 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 0.03(7) _refine_ls_number_reflns 17215 _refine_ls_number_parameters 924 _refine_ls_number_restraints 220 _refine_ls_R_factor_all 0.0833 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.1858 _refine_ls_wR_factor_gt 0.1791 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.040 _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 S1A S 0.22652(16) 0.67129(13) 1.42122(10) 0.0331(4) Uiso 0.691(3) 1 d PD A 1 S2A S 0.32941(18) 0.61100(12) 1.35851(10) 0.0321(4) Uiso 0.691(3) 1 d PD A 1 S1A' S 0.2097(4) 0.6968(3) 1.4326(2) 0.0331(4) Uiso 0.309(3) 1 d PD A 2 S2A' S 0.3559(4) 0.5916(3) 1.3438(2) 0.0321(4) Uiso 0.309(3) 1 d PD A 2 S3A' S 0.3012(5) 0.5947(3) 1.4394(3) 0.0540(14) Uiso 0.309(3) 1 d P A 2 N1A N 0.1203(3) 0.7013(2) 1.2965(2) 0.0283(8) Uani 1 1 d . A . C2A C 0.0712(4) 0.7792(3) 1.2782(2) 0.0308(9) Uani 1 1 d . . . H2A1 H 0.0068 0.7748 1.2424 0.037 Uiso 1 1 calc R . . H2A2 H 0.1323 0.8144 1.2613 0.037 Uiso 1 1 calc R . . C3A C 0.0259(4) 0.8084(3) 1.3466(3) 0.0348(11) Uani 1 1 d . . . H3A H -0.0454 0.8418 1.3389 0.042 Uiso 1 1 calc R . . O3A O 0.1140(3) 0.8476(2) 1.38849(18) 0.0357(8) Uani 1 1 d . . . C4A C -0.0019(5) 0.7340(3) 1.3849(3) 0.0388(11) Uani 1 1 d . A . H4A1 H 0.0029 0.7429 1.4354 0.047 Uiso 1 1 calc R . . H4A2 H -0.0815 0.7151 1.3712 0.047 Uiso 1 1 calc R . . C5A C 0.0899(4) 0.6759(3) 1.3646(2) 0.0314(10) Uani 1 1 d D . . C6A C 0.0529(4) 0.5895(3) 1.3647(2) 0.0308(10) Uani 1 1 d . A . O6A O -0.0253(3) 0.5649(2) 1.40053(17) 0.0372(8) Uani 1 1 d . . . N7A N 0.1188(3) 0.5452(2) 1.3252(2) 0.0310(8) Uani 1 1 d . . . C8A C 0.1126(4) 0.4599(3) 1.3183(3) 0.0351(11) Uani 1 1 d . A . H8A1 H 0.0400 0.4440 1.2921 0.042 Uiso 1 1 calc R . . H8A2 H 0.1146 0.4345 1.3642 0.042 Uiso 1 1 calc R . . C9A C 0.2204(4) 0.4383(3) 1.2793(3) 0.0366(11) Uani 1 1 d . . . H9A H 0.1997 0.3977 1.2436 0.044 Uiso 1 1 calc R A . O9A O 0.3067(3) 0.4090(2) 1.3272(2) 0.0396(8) Uani 1 1 d . A . C10A C 0.2555(4) 0.5142(3) 1.2443(3) 0.0342(10) Uani 1 1 d . A . H10A H 0.3414 0.5165 1.2400 0.041 Uiso 1 1 calc R . . H10B H 0.2166 0.5186 1.1977 0.041 Uiso 1 1 calc R . . C11A C 0.2153(3) 0.5787(3) 1.2908(2) 0.0281(9) Uani 1 1 d D A . C12A C 0.1795(4) 0.6549(3) 1.2545(2) 0.0263(9) Uani 1 1 d . . . O12A O 0.2030(3) 0.67102(19) 1.19577(16) 0.0307(7) Uani 1 1 d . A . C13A C 0.1328(5) 0.9262(3) 1.3671(3) 0.0420(12) Uani 1 1 d . . . H13A H 0.0586 0.9560 1.3675 0.050 Uiso 1 1 calc R . . H13B H 0.1605 0.9268 1.3195 0.050 Uiso 1 1 calc R . . C14A C 0.2225(5) 0.9628(3) 1.4155(3) 0.0332(10) Uani 1 1 d . . . C15A C 0.3378(5) 0.9676(3) 1.3986(3) 0.0404(12) Uani 1 1 d . . . H15A H 0.3603 0.9466 1.3558 0.048 Uiso 1 1 calc R . . C16A C 0.4219(5) 1.0023(4) 1.4424(3) 0.0469(13) Uani 1 1 d . . . H16A H 0.5011 1.0047 1.4299 0.056 Uiso 1 1 calc R . . C17A C 0.3898(5) 1.0335(3) 1.5049(3) 0.0405(12) Uani 1 1 d . . . H17A H 0.4468 1.0576 1.5352 0.049 Uiso 1 1 calc R . . C18A C 0.2753(5) 1.0292(3) 1.5225(3) 0.0389(11) Uani 1 1 d . . . H18A H 0.2530 1.0510 1.5650 0.047 Uiso 1 1 calc R . . C19A C 0.1912(5) 0.9934(3) 1.4789(3) 0.0359(10) Uani 1 1 d . . . H19A H 0.1125 0.9897 1.4922 0.043 Uiso 1 1 calc R . . C20A C 0.4059(6) 0.3803(4) 1.2927(4) 0.0600(18) Uani 1 1 d . . . H20A H 0.4572 0.4244 1.2808 0.072 Uiso 1 1 calc R A . H20B H 0.3796 0.3535 1.2495 0.072 Uiso 1 1 calc R . . C21A C 0.4729(4) 0.3236(3) 1.3400(3) 0.0398(11) Uani 1 1 d . A . C22A C 0.5155(6) 0.3448(4) 1.4046(3) 0.0495(14) Uani 1 1 d . . . H22A H 0.5003 0.3958 1.4214 0.059 Uiso 1 1 calc R A . C23A C 0.5805(6) 0.2927(5) 1.4456(3) 0.0563(16) Uani 1 1 d . A . H23A H 0.6109 0.3084 1.4899 0.068 Uiso 1 1 calc R . . C24A C 0.6010(6) 0.2182(4) 1.4220(4) 0.0600(17) Uani 1 1 d . . . H24A H 0.6431 0.1818 1.4506 0.072 Uiso 1 1 calc R A . C25A C 0.5606(7) 0.1970(4) 1.3574(4) 0.069(2) Uani 1 1 d . A . H25A H 0.5782 0.1465 1.3403 0.082 Uiso 1 1 calc R . . C26A C 0.4938(6) 0.2483(4) 1.3162(4) 0.0581(17) Uani 1 1 d . . . H26A H 0.4627 0.2321 1.2722 0.070 Uiso 1 1 calc R A . S1B S 0.40274(10) 0.32367(7) 1.84749(6) 0.0319(2) Uani 1 1 d D . . S2B S 0.29335(9) 0.26016(7) 1.77987(6) 0.0302(2) Uani 1 1 d D . . N1B N 0.5228(3) 0.1847(2) 1.8345(2) 0.0264(7) Uani 1 1 d . . . C2B C 0.5797(4) 0.1464(3) 1.8957(2) 0.0270(9) Uani 1 1 d . . . H2B1 H 0.6490 0.1159 1.8830 0.032 Uiso 1 1 calc R . . H2B2 H 0.5244 0.1114 1.9185 0.032 Uiso 1 1 calc R . . C3B C 0.6151(4) 0.2149(3) 1.9419(2) 0.0282(9) Uani 1 1 d . . . H3B H 0.6887 0.2032 1.9700 0.034 Uiso 1 1 calc R . . O3B O 0.5201(3) 0.2299(2) 1.98507(16) 0.0294(7) Uani 1 1 d . . . C4B C 0.6334(4) 0.2824(3) 1.8920(2) 0.0279(9) Uani 1 1 d . . . H4B1 H 0.7133 0.2812 1.8745 0.033 Uiso 1 1 calc R . . H4B2 H 0.6206 0.3334 1.9145 0.033 Uiso 1 1 calc R . . C5B C 0.5410(3) 0.2678(2) 1.8336(2) 0.0258(8) Uani 1 1 d D . . C6B C 0.5726(4) 0.2953(3) 1.7615(2) 0.0270(9) Uani 1 1 d . . . O6B O 0.6507(3) 0.3424(2) 1.75121(18) 0.0322(7) Uani 1 1 d . . . N7B N 0.5006(3) 0.2635(2) 1.71256(19) 0.0263(7) Uani 1 1 d . . . C8B C 0.4974(4) 0.2821(3) 1.6391(2) 0.0305(9) Uani 1 1 d . . . H8B1 H 0.5674 0.2613 1.6172 0.037 Uiso 1 1 calc R . . H8B2 H 0.4935 0.3393 1.6316 0.037 Uiso 1 1 calc R . . C9B C 0.3856(4) 0.2420(3) 1.6101(2) 0.0309(9) Uani 1 1 d . . . H9B H 0.3975 0.2194 1.5635 0.037 Uiso 1 1 calc R . . O9B O 0.2869(3) 0.2924(2) 1.60844(18) 0.0342(7) Uani 1 1 d . . . C10B C 0.3621(4) 0.1773(3) 1.6627(2) 0.0296(9) Uani 1 1 d . . . H10C H 0.2771 0.1670 1.6645 0.035 Uiso 1 1 calc R . . H10D H 0.4022 0.1283 1.6505 0.035 Uiso 1 1 calc R . . C11B C 0.4115(3) 0.2091(2) 1.7316(2) 0.0241(8) Uani 1 1 d D . . C12B C 0.4609(4) 0.1495(3) 1.7833(2) 0.0260(8) Uani 1 1 d . . . O12B O 0.4437(3) 0.07835(18) 1.77866(18) 0.0312(7) Uani 1 1 d . . . C13B C 0.5502(4) 0.2790(3) 2.0424(3) 0.0348(10) Uani 1 1 d . . . H13C H 0.5909 0.3266 2.0271 0.042 Uiso 1 1 calc R . . H13D H 0.6023 0.2511 2.0764 0.042 Uiso 1 1 calc R . . C14B C 0.4357(4) 0.3003(3) 2.0738(2) 0.0306(9) Uani 1 1 d . . . C15B C 0.3676(5) 0.2437(3) 2.1030(3) 0.0353(10) Uani 1 1 d . . . H15B H 0.3969 0.1919 2.1081 0.042 Uiso 1 1 calc R . . C16B C 0.2573(5) 0.2614(4) 2.1250(3) 0.0436(12) Uani 1 1 d . . . H16B H 0.2101 0.2219 2.1439 0.052 Uiso 1 1 calc R . . C17B C 0.2164(5) 0.3374(4) 2.1191(3) 0.0508(15) Uani 1 1 d . . . H17B H 0.1405 0.3498 2.1338 0.061 Uiso 1 1 calc R . . C18B C 0.2845(5) 0.3951(4) 2.0922(3) 0.0490(14) Uani 1 1 d . . . H18B H 0.2568 0.4474 2.0896 0.059 Uiso 1 1 calc R . . C19B C 0.3951(5) 0.3761(3) 2.0688(3) 0.0384(11) Uani 1 1 d . . . H19B H 0.4421 0.4155 2.0495 0.046 Uiso 1 1 calc R . . C20B C 0.2867(5) 0.3512(3) 1.5557(3) 0.0387(11) Uani 1 1 d . . . H20C H 0.2386 0.3337 1.5147 0.046 Uiso 1 1 calc R . . H20D H 0.3676 0.3604 1.5414 0.046 Uiso 1 1 calc R . . C21B C 0.2364(4) 0.4261(3) 1.5840(2) 0.0335(10) Uani 1 1 d . . . C22B C 0.1735(5) 0.4773(3) 1.5407(3) 0.0447(13) Uani 1 1 d . . . H22B H 0.1613 0.4647 1.4932 0.054 Uiso 1 1 calc R . . C23B C 0.1283(6) 0.5463(4) 1.5658(3) 0.0526(15) Uani 1 1 d . . . H23B H 0.0841 0.5799 1.5355 0.063 Uiso 1 1 calc R . . C24B C 0.1466(7) 0.5660(3) 1.6328(4) 0.0541(16) Uani 1 1 d . . . H24B H 0.1161 0.6135 1.6499 0.065 Uiso 1 1 calc R . . C25B C 0.2110(6) 0.5156(4) 1.6767(3) 0.0503(14) Uani 1 1 d . . . H25B H 0.2244 0.5289 1.7240 0.060 Uiso 1 1 calc R . . C26B C 0.2554(5) 0.4466(3) 1.6521(3) 0.0452(13) Uani 1 1 d . . . H26B H 0.2995 0.4130 1.6825 0.054 Uiso 1 1 calc R . . S1C S 0.90675(10) 0.41792(7) 1.11640(6) 0.0323(2) Uani 1 1 d D . . S2C S 1.00445(10) 0.51970(7) 1.10805(7) 0.0345(3) Uani 1 1 d D . . N1C N 0.8114(3) 0.5120(2) 1.21466(18) 0.0240(7) Uani 1 1 d . . . C2C C 0.7738(4) 0.4826(3) 1.2812(2) 0.0297(9) Uani 1 1 d . . . H2C1 H 0.7053 0.5121 1.2967 0.036 Uiso 1 1 calc R . . H2C2 H 0.8381 0.4859 1.3172 0.036 Uiso 1 1 calc R . . C3C C 0.7418(4) 0.3981(3) 1.2652(2) 0.0296(9) Uani 1 1 d . . . H3C H 0.6774 0.3799 1.2943 0.036 Uiso 1 1 calc R . . O3C O 0.8420(3) 0.34767(19) 1.27315(17) 0.0309(7) Uani 1 1 d . . . C4C C 0.7016(4) 0.3990(3) 1.1886(2) 0.0298(9) Uani 1 1 d . . . H4C1 H 0.7156 0.3477 1.1669 0.036 Uiso 1 1 calc R . . H4C2 H 0.6173 0.4118 1.1828 0.036 Uiso 1 1 calc R . . C5C C 0.7763(4) 0.4625(2) 1.1572(2) 0.0250(8) Uani 1 1 d D . . C6C C 0.7178(4) 0.5094(3) 1.0973(2) 0.0259(8) Uani 1 1 d . . . O6C O 0.6318(3) 0.4893(2) 1.06401(18) 0.0353(8) Uani 1 1 d . . . N7C N 0.7797(3) 0.5758(2) 1.08634(19) 0.0265(7) Uani 1 1 d . . . C8C C 0.7583(4) 0.6305(3) 1.0291(3) 0.0327(10) Uani 1 1 d . . . H8C1 H 0.6871 0.6621 1.0359 0.039 Uiso 1 1 calc R . . H8C2 H 0.7488 0.6024 0.9846 0.039 Uiso 1 1 calc R . . C9C C 0.8677(4) 0.6822(3) 1.0311(2) 0.0290(9) Uani 1 1 d . . . H9C H 0.8466 0.7378 1.0208 0.035 Uiso 1 1 calc R . . O9C O 0.9447(3) 0.65233(19) 0.98148(17) 0.0305(7) Uani 1 1 d . . . C10C C 0.9205(4) 0.6736(3) 1.1057(2) 0.0287(9) Uani 1 1 d . . . H10E H 1.0068 0.6792 1.1069 0.034 Uiso 1 1 calc R . . H10F H 0.8877 0.7133 1.1365 0.034 Uiso 1 1 calc R . . C11C C 0.8857(4) 0.5914(2) 1.1272(2) 0.0256(8) Uani 1 1 d D . . C12C C 0.8660(4) 0.5804(3) 1.2037(2) 0.0248(8) Uani 1 1 d . . . O12C O 0.8974(3) 0.6272(2) 1.24870(17) 0.0333(7) Uani 1 1 d . . . C13C C 0.8641(4) 0.3273(3) 1.3440(2) 0.0365(11) Uani 1 1 d . . . H13E H 0.7971 0.2969 1.3604 0.044 Uiso 1 1 calc R . . H13F H 0.8716 0.3755 1.3721 0.044 Uiso 1 1 calc R . . C14C C 0.9743(4) 0.2798(3) 1.3536(3) 0.0313(9) Uani 1 1 d . . . C15C C 1.0491(4) 0.2652(3) 1.3009(3) 0.0362(10) Uani 1 1 d . . . H15C H 1.0307 0.2849 1.2559 0.043 Uiso 1 1 calc R . . C16C C 1.1492(5) 0.2227(3) 1.3133(3) 0.0459(13) Uani 1 1 d . . . H16C H 1.2009 0.2148 1.2771 0.055 Uiso 1 1 calc R . . C17C C 1.1768(5) 0.1908(3) 1.3778(3) 0.0459(13) Uani 1 1 d . . . H17C H 1.2452 0.1599 1.3857 0.055 Uiso 1 1 calc R . . C18C C 1.1029(6) 0.2049(4) 1.4296(3) 0.0492(14) Uani 1 1 d . . . H18C H 1.1209 0.1840 1.4742 0.059 Uiso 1 1 calc R . . C19C C 1.0023(5) 0.2490(4) 1.4183(3) 0.0473(14) Uani 1 1 d . . . H19C H 0.9523 0.2582 1.4552 0.057 Uiso 1 1 calc R . . C20C C 1.0328(4) 0.7083(3) 0.9662(3) 0.0360(11) Uani 1 1 d . . . H20E H 1.0708 0.7281 1.0098 0.043 Uiso 1 1 calc R . . H20F H 0.9962 0.7532 0.9412 0.043 Uiso 1 1 calc R . . C21C C 1.1230(4) 0.6718(3) 0.9230(2) 0.0336(10) Uani 1 1 d . . . C22C C 1.1874(5) 0.6080(3) 0.9483(3) 0.0393(11) Uani 1 1 d . . . H22C H 1.1712 0.5860 0.9918 0.047 Uiso 1 1 calc R . . C23C C 1.2752(6) 0.5770(4) 0.9100(4) 0.0575(17) Uani 1 1 d . . . H23C H 1.3180 0.5326 0.9265 0.069 Uiso 1 1 calc R . . C24C C 1.3007(7) 0.6109(5) 0.8471(4) 0.071(2) Uani 1 1 d . . . H24C H 1.3636 0.5913 0.8219 0.085 Uiso 1 1 calc R . . C25C C 1.2349(7) 0.6726(5) 0.8215(4) 0.067(2) Uani 1 1 d . . . H25C H 1.2505 0.6944 0.7779 0.081 Uiso 1 1 calc R . . C26C C 1.1460(5) 0.7028(4) 0.8593(3) 0.0454(13) Uani 1 1 d . . . H26C H 1.1003 0.7451 0.8413 0.055 Uiso 1 1 calc R . . C1S C 1.3837(6) 0.0001(5) 1.1948(3) 0.0464(18) Uiso 0.529(2) 1 d PDU B 1 H1S H 1.3441 -0.0515 1.1999 0.056 Uiso 0.529(2) 1 calc PR B 1 Cl1 Cl 1.4200(3) 0.0103(2) 1.10817(17) 0.0572(6) Uiso 0.529(2) 1 d PDU B 1 Cl2 Cl 1.5073(3) 0.0020(2) 1.25166(18) 0.0658(6) Uiso 0.529(2) 1 d PDU B 1 Cl3 Cl 1.2855(3) 0.0736(2) 1.21738(19) 0.0678(7) Uiso 0.529(2) 1 d PDU B 1 C1S' C 1.3210(6) 0.0110(6) 1.1866(4) 0.0464(18) Uiso 0.471(2) 1 d PDU B 2 H1S' H 1.3117 -0.0435 1.2040 0.056 Uiso 0.471(2) 1 calc PR B 2 Cl1' Cl 1.1846(3) 0.0579(2) 1.18421(19) 0.0572(6) Uiso 0.471(2) 1 d PDU B 2 Cl2' Cl 1.4139(4) 0.0631(2) 1.2446(2) 0.0658(6) Uiso 0.471(2) 1 d PDU B 2 Cl3' Cl 1.3762(5) 0.0075(3) 1.1044(2) 0.0678(7) Uiso 0.471(2) 1 d PDU B 2 C2S C 0.9766(5) 0.9367(5) 1.1027(3) 0.0448(17) Uiso 0.632(3) 1 d PDU C 1 H2S H 0.9970 0.9917 1.0905 0.054 Uiso 0.632(3) 1 calc PR C 1 Cl4 Cl 0.8740(3) 0.90244(18) 1.04114(16) 0.0578(6) Uiso 0.632(3) 1 d PDU C 1 Cl5 Cl 1.1046(3) 0.88001(19) 1.10194(15) 0.0634(6) Uiso 0.632(3) 1 d PDU C 1 Cl6 Cl 0.9198(3) 0.9369(2) 1.18507(18) 0.0802(8) Uiso 0.632(3) 1 d PDU C 1 C2S' C 1.0055(6) 0.9630(7) 1.0991(5) 0.0448(17) Uiso 0.368(3) 1 d PDU C 2 H2S' H 1.0010 1.0137 1.0733 0.054 Uiso 0.368(3) 1 calc PR C 2 Cl4' Cl 0.9793(4) 0.9800(3) 1.1863(2) 0.0578(6) Uiso 0.368(3) 1 d PDU C 2 Cl5' Cl 1.1423(4) 0.9196(3) 1.0881(3) 0.0634(6) Uiso 0.368(3) 1 d PDU C 2 Cl6' Cl 0.8933(6) 0.9005(4) 1.0670(4) 0.0802(8) Uiso 0.368(3) 1 d PDU C 2 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 N1A 0.0306(19) 0.0276(19) 0.0272(19) 0.0001(15) 0.0064(15) -0.0023(15) C2A 0.031(2) 0.034(2) 0.027(2) -0.0057(18) 0.0008(17) 0.0032(18) C3A 0.025(2) 0.044(3) 0.036(2) -0.013(2) 0.0010(18) 0.0042(19) O3A 0.0424(19) 0.0318(17) 0.0327(17) -0.0072(14) -0.0007(14) -0.0004(15) C4A 0.036(3) 0.047(3) 0.035(3) -0.008(2) 0.014(2) -0.006(2) C5A 0.027(2) 0.045(3) 0.022(2) 0.0014(19) 0.0010(16) -0.006(2) C6A 0.029(2) 0.041(3) 0.023(2) 0.0008(18) 0.0018(17) -0.0047(19) O6A 0.0294(17) 0.053(2) 0.0290(17) 0.0060(15) 0.0050(13) -0.0098(15) N7A 0.0236(18) 0.032(2) 0.037(2) 0.0049(16) 0.0001(15) -0.0106(15) C8A 0.026(2) 0.032(2) 0.047(3) 0.009(2) -0.001(2) -0.0047(18) C9A 0.032(2) 0.036(3) 0.042(3) 0.009(2) 0.001(2) 0.002(2) O9A 0.0342(18) 0.0369(19) 0.048(2) 0.0110(16) 0.0038(15) 0.0037(15) C10A 0.037(2) 0.030(2) 0.036(2) 0.004(2) 0.008(2) 0.007(2) C11A 0.0205(19) 0.035(2) 0.029(2) 0.0044(18) 0.0023(16) -0.0039(17) C12A 0.0217(19) 0.030(2) 0.028(2) 0.0001(17) 0.0070(16) -0.0028(17) O12A 0.0377(17) 0.0276(16) 0.0279(15) 0.0034(13) 0.0121(13) 0.0016(13) C13A 0.055(3) 0.032(3) 0.038(3) -0.007(2) -0.007(2) 0.004(2) C14A 0.044(3) 0.023(2) 0.032(2) 0.0000(18) -0.004(2) 0.0066(19) C15A 0.056(3) 0.039(3) 0.026(2) -0.008(2) 0.006(2) 0.015(2) C16A 0.038(3) 0.050(3) 0.052(3) 0.001(3) 0.009(2) 0.007(2) C17A 0.044(3) 0.032(3) 0.044(3) -0.001(2) -0.003(2) -0.004(2) C18A 0.049(3) 0.037(3) 0.030(2) -0.010(2) 0.001(2) 0.002(2) C19A 0.035(2) 0.037(3) 0.036(3) -0.003(2) 0.004(2) 0.001(2) C20A 0.052(4) 0.060(4) 0.069(4) 0.032(3) 0.020(3) 0.022(3) C21A 0.029(2) 0.039(3) 0.051(3) 0.013(2) 0.005(2) 0.003(2) C22A 0.057(4) 0.048(3) 0.044(3) -0.005(3) 0.016(3) 0.003(3) C23A 0.053(4) 0.081(5) 0.035(3) 0.004(3) 0.003(3) -0.003(3) C24A 0.054(4) 0.064(4) 0.060(4) 0.016(3) -0.015(3) -0.003(3) C25A 0.085(5) 0.042(3) 0.076(5) 0.003(3) -0.026(4) 0.004(3) C26A 0.061(4) 0.044(3) 0.066(4) 0.001(3) -0.024(3) -0.002(3) S1B 0.0280(5) 0.0305(5) 0.0374(6) -0.0092(5) 0.0044(4) 0.0024(4) S2B 0.0229(5) 0.0349(6) 0.0330(6) -0.0045(5) 0.0045(4) -0.0005(4) N1B 0.0249(17) 0.0233(17) 0.0307(18) -0.0040(14) 0.0002(14) 0.0003(14) C2B 0.028(2) 0.027(2) 0.026(2) -0.0008(17) 0.0035(16) 0.0014(17) C3B 0.023(2) 0.028(2) 0.034(2) -0.0071(18) 0.0047(17) -0.0002(16) O3B 0.0275(16) 0.0345(17) 0.0268(15) -0.0065(13) 0.0061(12) -0.0009(13) C4B 0.0223(19) 0.031(2) 0.031(2) -0.0057(17) 0.0025(16) -0.0071(17) C5B 0.0251(19) 0.0183(19) 0.034(2) -0.0055(16) 0.0069(16) -0.0022(16) C6B 0.0195(19) 0.027(2) 0.035(2) -0.0032(17) 0.0071(16) -0.0003(16) O6B 0.0268(16) 0.0329(17) 0.0373(18) 0.0005(14) 0.0051(13) -0.0061(13) N7B 0.0256(17) 0.0262(18) 0.0275(18) -0.0008(15) 0.0068(14) -0.0017(15) C8B 0.027(2) 0.031(2) 0.034(2) 0.0011(18) 0.0055(17) 0.0009(18) C9B 0.033(2) 0.030(2) 0.029(2) -0.0012(18) 0.0021(18) 0.0018(18) O9B 0.0313(17) 0.0367(18) 0.0345(17) 0.0069(14) 0.0007(13) 0.0047(14) C10B 0.031(2) 0.024(2) 0.034(2) -0.0027(18) 0.0017(17) -0.0012(18) C11B 0.0228(19) 0.0187(18) 0.031(2) -0.0018(16) 0.0070(16) -0.0040(15) C12B 0.024(2) 0.027(2) 0.028(2) -0.0031(16) 0.0042(16) -0.0018(16) O12B 0.0344(17) 0.0221(15) 0.0369(18) -0.0042(13) -0.0014(13) -0.0059(13) C13B 0.031(2) 0.039(3) 0.034(2) -0.014(2) 0.0003(18) -0.002(2) C14B 0.033(2) 0.028(2) 0.031(2) -0.0062(17) 0.0004(18) -0.0058(18) C15B 0.040(3) 0.032(2) 0.033(2) -0.0022(19) -0.001(2) -0.003(2) C16B 0.044(3) 0.057(3) 0.031(2) -0.002(2) 0.007(2) -0.010(3) C17B 0.036(3) 0.059(4) 0.057(4) -0.023(3) 0.001(2) 0.004(3) C18B 0.049(3) 0.036(3) 0.062(4) -0.013(3) 0.001(3) 0.007(2) C19B 0.038(3) 0.031(2) 0.045(3) -0.003(2) -0.002(2) -0.001(2) C20B 0.041(3) 0.043(3) 0.032(2) 0.008(2) 0.001(2) 0.005(2) C21B 0.035(2) 0.035(2) 0.031(2) 0.0028(19) 0.0025(18) -0.001(2) C22B 0.057(3) 0.043(3) 0.034(3) 0.011(2) -0.004(2) 0.000(3) C23B 0.071(4) 0.032(3) 0.054(4) 0.010(2) 0.004(3) 0.004(3) C24B 0.079(5) 0.025(3) 0.059(4) 0.001(2) 0.012(3) -0.004(3) C25B 0.074(4) 0.039(3) 0.038(3) -0.003(2) 0.005(3) -0.009(3) C26B 0.053(3) 0.044(3) 0.037(3) 0.002(2) -0.008(2) -0.001(3) S1C 0.0348(6) 0.0257(5) 0.0370(6) -0.0007(4) 0.0089(5) 0.0051(4) S2C 0.0265(5) 0.0312(6) 0.0465(7) 0.0068(5) 0.0082(5) 0.0050(4) N1C 0.0250(16) 0.0254(17) 0.0217(16) -0.0002(14) 0.0015(13) -0.0023(14) C2C 0.030(2) 0.032(2) 0.027(2) -0.0010(18) 0.0028(17) 0.0045(18) C3C 0.029(2) 0.031(2) 0.029(2) 0.0028(18) 0.0074(17) -0.0039(18) O3C 0.0372(17) 0.0274(16) 0.0285(16) 0.0084(13) 0.0045(13) 0.0029(13) C4C 0.027(2) 0.029(2) 0.033(2) 0.0034(18) 0.0002(17) -0.0048(17) C5C 0.027(2) 0.0227(19) 0.025(2) -0.0024(16) -0.0023(16) 0.0005(16) C6C 0.028(2) 0.026(2) 0.0232(19) 0.0011(16) 0.0024(16) 0.0026(17) O6C 0.0327(17) 0.0389(19) 0.0338(18) 0.0026(14) -0.0037(14) -0.0063(14) N7C 0.0278(18) 0.0244(17) 0.0269(18) 0.0040(14) -0.0020(14) -0.0013(14) C8C 0.029(2) 0.036(2) 0.033(2) 0.0097(19) -0.0045(18) -0.0023(18) C9C 0.030(2) 0.022(2) 0.034(2) 0.0069(17) -0.0025(17) -0.0005(17) O9C 0.0347(17) 0.0267(16) 0.0302(16) 0.0036(13) 0.0029(13) -0.0098(13) C10C 0.029(2) 0.028(2) 0.029(2) 0.0014(17) 0.0005(17) -0.0011(18) C11C 0.025(2) 0.023(2) 0.029(2) 0.0017(16) -0.0008(16) 0.0020(16) C12C 0.0207(19) 0.026(2) 0.027(2) -0.0020(16) -0.0002(15) 0.0011(16) O12C 0.0413(19) 0.0306(17) 0.0269(16) 0.0004(13) -0.0079(14) -0.0080(14) C13C 0.034(2) 0.049(3) 0.027(2) 0.013(2) 0.0063(18) 0.004(2) C14C 0.033(2) 0.025(2) 0.036(2) 0.0040(18) 0.0034(18) -0.0021(18) C15C 0.039(3) 0.036(3) 0.033(2) 0.003(2) 0.0040(19) 0.004(2) C16C 0.053(3) 0.042(3) 0.043(3) 0.000(2) 0.010(2) 0.007(3) C17C 0.049(3) 0.041(3) 0.046(3) -0.002(2) -0.004(2) 0.012(2) C18C 0.064(4) 0.049(3) 0.034(3) 0.007(2) -0.001(3) 0.020(3) C19C 0.055(3) 0.054(3) 0.033(3) 0.005(2) 0.006(2) 0.016(3) C20C 0.038(3) 0.026(2) 0.044(3) 0.004(2) 0.008(2) -0.0105(19) C21C 0.035(2) 0.036(3) 0.029(2) -0.0049(19) 0.0014(18) -0.016(2) C22C 0.043(3) 0.032(2) 0.043(3) -0.009(2) 0.004(2) -0.015(2) C23C 0.061(4) 0.041(3) 0.071(4) -0.020(3) 0.017(3) -0.010(3) C24C 0.068(4) 0.066(5) 0.083(5) -0.048(4) 0.036(4) -0.023(4) C25C 0.092(5) 0.067(5) 0.046(3) -0.021(3) 0.028(4) -0.038(4) C26C 0.056(3) 0.046(3) 0.035(3) 0.000(2) 0.005(2) -0.018(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1A C5A 1.867(4) . ? S1A S2A 2.016(4) . ? S2A C11A 1.888(4) . ? S1A' C5A 1.890(5) . ? S1A' S3A' 2.036(8) . ? S2A' C11A 1.878(5) . ? S2A' S3A' 1.986(7) . ? N1A C12A 1.344(6) . ? N1A C5A 1.449(6) . ? N1A C2A 1.481(6) . ? C2A C3A 1.532(6) . ? C2A H2A1 0.9900 . ? C2A H2A2 0.9900 . ? C3A O3A 1.430(6) . ? C3A C4A 1.515(8) . ? C3A H3A 1.0000 . ? O3A C13A 1.426(7) . ? C4A C5A 1.512(7) . ? C4A H4A1 0.9900 . ? C4A H4A2 0.9900 . ? C5A C6A 1.538(7) . ? C6A O6A 1.232(6) . ? C6A N7A 1.336(6) . ? N7A C11A 1.435(6) . ? N7A C8A 1.467(6) . ? C8A C9A 1.523(7) . ? C8A H8A1 0.9900 . ? C8A H8A2 0.9900 . ? C9A O9A 1.414(6) . ? C9A C10A 1.527(7) . ? C9A H9A 1.0000 . ? O9A C20A 1.430(7) . ? C10A C11A 1.511(7) . ? C10A H10A 0.9900 . ? C10A H10B 0.9900 . ? C11A C12A 1.527(6) . ? C12A O12A 1.215(5) . ? C13A C14A 1.494(7) . ? C13A H13A 0.9900 . ? C13A H13B 0.9900 . ? C14A C15A 1.376(8) . ? C14A C19A 1.399(7) . ? C15A C16A 1.386(8) . ? C15A H15A 0.9500 . ? C16A C17A 1.390(8) . ? C16A H16A 0.9500 . ? C17A C18A 1.370(8) . ? C17A H17A 0.9500 . ? C18A C19A 1.392(7) . ? C18A H18A 0.9500 . ? C19A H19A 0.9500 . ? C20A C21A 1.517(8) . ? C20A H20A 0.9900 . ? C20A H20B 0.9900 . ? C21A C22A 1.370(9) . ? C21A C26A 1.393(9) . ? C22A C23A 1.386(9) . ? C22A H22A 0.9500 . ? C23A C24A 1.379(11) . ? C23A H23A 0.9500 . ? C24A C25A 1.363(10) . ? C24A H24A 0.9500 . ? C25A C26A 1.389(9) . ? C25A H25A 0.9500 . ? C26A H26A 0.9500 . ? S1B C5B 1.877(4) . ? S1B S2B 2.0748(16) . ? S2B C11B 1.894(4) . ? N1B C12B 1.335(6) . ? N1B C5B 1.438(5) . ? N1B C2B 1.478(6) . ? C2B C3B 1.519(6) . ? C2B H2B1 0.9900 . ? C2B H2B2 0.9900 . ? C3B O3B 1.425(5) . ? C3B C4B 1.528(7) . ? C3B H3B 1.0000 . ? O3B C13B 1.423(5) . ? C4B C5B 1.530(6) . ? C4B H4B1 0.9900 . ? C4B H4B2 0.9900 . ? C5B C6B 1.534(6) . ? C6B O6B 1.226(5) . ? C6B N7B 1.342(6) . ? N7B C11B 1.440(5) . ? N7B C8B 1.459(6) . ? C8B C9B 1.534(7) . ? C8B H8B1 0.9900 . ? C8B H8B2 0.9900 . ? C9B O9B 1.419(6) . ? C9B C10B 1.536(6) . ? C9B H9B 1.0000 . ? O9B C20B 1.435(6) . ? C10B C11B 1.526(6) . ? C10B H10C 0.9900 . ? C10B H10D 0.9900 . ? C11B C12B 1.520(6) . ? C12B O12B 1.235(5) . ? C13B C14B 1.514(7) . ? C13B H13C 0.9900 . ? C13B H13D 0.9900 . ? C14B C19B 1.380(7) . ? C14B C15B 1.382(7) . ? C15B C16B 1.384(8) . ? C15B H15B 0.9500 . ? C16B C17B 1.384(9) . ? C16B H16B 0.9500 . ? C17B C18B 1.376(9) . ? C17B H17B 0.9500 . ? C18B C19B 1.402(8) . ? C18B H18B 0.9500 . ? C19B H19B 0.9500 . ? C20B C21B 1.519(7) . ? C20B H20C 0.9900 . ? C20B H20D 0.9900 . ? C21B C26B 1.373(7) . ? C21B C22B 1.389(7) . ? C22B C23B 1.386(9) . ? C22B H22B 0.9500 . ? C23B C24B 1.350(9) . ? C23B H23B 0.9500 . ? C24B C25B 1.397(9) . ? C24B H24B 0.9500 . ? C25B C26B 1.378(9) . ? C25B H25B 0.9500 . ? C26B H26B 0.9500 . ? S1C C5C 1.883(4) . ? S1C S2C 2.0789(17) . ? S2C C11C 1.880(4) . ? N1C C12C 1.347(6) . ? N1C C5C 1.442(5) . ? N1C C2C 1.469(6) . ? C2C C3C 1.519(7) . ? C2C H2C1 0.9900 . ? C2C H2C2 0.9900 . ? C3C O3C 1.436(6) . ? C3C C4C 1.533(6) . ? C3C H3C 1.0000 . ? O3C C13C 1.429(5) . ? C4C C5C 1.526(6) . ? C4C H4C1 0.9900 . ? C4C H4C2 0.9900 . ? C5C C6C 1.538(6) . ? C6C O6C 1.200(6) . ? C6C N7C 1.361(6) . ? N7C C11C 1.440(5) . ? N7C C8C 1.463(6) . ? C8C C9C 1.530(6) . ? C8C H8C1 0.9900 . ? C8C H8C2 0.9900 . ? C9C O9C 1.429(6) . ? C9C C10C 1.548(6) . ? C9C H9C 1.0000 . ? O9C C20C 1.431(5) . ? C10C C11C 1.525(6) . ? C10C H10E 0.9900 . ? C10C H10F 0.9900 . ? C11C C12C 1.522(6) . ? C12C O12C 1.225(5) . ? C13C C14C 1.502(7) . ? C13C H13E 0.9900 . ? C13C H13F 0.9900 . ? C14C C19C 1.386(7) . ? C14C C15C 1.387(7) . ? C15C C16C 1.368(8) . ? C15C H15C 0.9500 . ? C16C C17C 1.387(8) . ? C16C H16C 0.9500 . ? C17C C18C 1.365(9) . ? C17C H17C 0.9500 . ? C18C C19C 1.384(8) . ? C18C H18C 0.9500 . ? C19C H19C 0.9500 . ? C20C C21C 1.496(7) . ? C20C H20E 0.9900 . ? C20C H20F 0.9900 . ? C21C C26C 1.383(7) . ? C21C C22C 1.391(8) . ? C22C C23C 1.383(8) . ? C22C H22C 0.9500 . ? C23C C24C 1.394(11) . ? C23C H23C 0.9500 . ? C24C C25C 1.375(13) . ? C24C H24C 0.9500 . ? C25C C26C 1.381(10) . ? C25C H25C 0.9500 . ? C26C H26C 0.9500 . ? C1S Cl2 1.750(6) . ? C1S Cl3 1.755(6) . ? C1S Cl1 1.759(6) . ? C1S H1S 1.0000 . ? C1S' Cl3' 1.743(6) . ? C1S' Cl1' 1.752(7) . ? C1S' Cl2' 1.754(7) . ? C1S' H1S' 1.0000 . ? C2S Cl4 1.734(6) . ? C2S Cl6 1.754(6) . ? C2S Cl5 1.755(6) . ? C2S H2S 1.0000 . ? C2S' Cl5' 1.754(7) . ? C2S' Cl4' 1.757(7) . ? C2S' Cl6' 1.760(7) . ? C2S' H2S' 1.0000 . ? 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 C5A S1A S2A 99.33(18) . . ? C11A S2A S1A 99.56(18) . . ? C5A S1A' S3A' 103.6(3) . . ? C11A S2A' S3A' 102.4(3) . . ? S2A' S3A' S1A' 98.4(3) . . ? C12A N1A C5A 121.6(4) . . ? C12A N1A C2A 125.6(4) . . ? C5A N1A C2A 112.6(4) . . ? N1A C2A C3A 103.0(4) . . ? N1A C2A H2A1 111.2 . . ? C3A C2A H2A1 111.2 . . ? N1A C2A H2A2 111.2 . . ? C3A C2A H2A2 111.2 . . ? H2A1 C2A H2A2 109.1 . . ? O3A C3A C4A 105.9(4) . . ? O3A C3A C2A 112.8(4) . . ? C4A C3A C2A 103.8(4) . . ? O3A C3A H3A 111.3 . . ? C4A C3A H3A 111.3 . . ? C2A C3A H3A 111.3 . . ? C13A O3A C3A 112.9(4) . . ? C5A C4A C3A 105.1(4) . . ? C5A C4A H4A1 110.7 . . ? C3A C4A H4A1 110.7 . . ? C5A C4A H4A2 110.7 . . ? C3A C4A H4A2 110.7 . . ? H4A1 C4A H4A2 108.8 . . ? N1A C5A C4A 103.9(4) . . ? N1A C5A C6A 111.6(4) . . ? C4A C5A C6A 116.0(4) . . ? N1A C5A S1A 108.6(3) . . ? C4A C5A S1A 116.4(3) . . ? C6A C5A S1A 100.4(3) . . ? N1A C5A S1A' 112.5(3) . . ? C4A C5A S1A' 100.4(4) . . ? C6A C5A S1A' 111.8(3) . . ? S1A C5A S1A' 16.18(15) . . ? O6A C6A N7A 125.1(5) . . ? O6A C6A C5A 122.4(4) . . ? N7A C6A C5A 112.4(4) . . ? C6A N7A C11A 120.5(4) . . ? C6A N7A C8A 126.1(4) . . ? C11A N7A C8A 113.0(4) . . ? N7A C8A C9A 104.4(4) . . ? N7A C8A H8A1 110.9 . . ? C9A C8A H8A1 110.9 . . ? N7A C8A H8A2 110.9 . . ? C9A C8A H8A2 110.9 . . ? H8A1 C8A H8A2 108.9 . . ? O9A C9A C8A 108.3(4) . . ? O9A C9A C10A 113.9(4) . . ? C8A C9A C10A 104.5(4) . . ? O9A C9A H9A 110.0 . . ? C8A C9A H9A 110.0 . . ? C10A C9A H9A 110.0 . . ? C9A O9A C20A 110.9(4) . . ? C11A C10A C9A 105.2(4) . . ? C11A C10A H10A 110.7 . . ? C9A C10A H10A 110.7 . . ? C11A C10A H10B 110.7 . . ? C9A C10A H10B 110.7 . . ? H10A C10A H10B 108.8 . . ? N7A C11A C10A 104.4(4) . . ? N7A C11A C12A 111.1(4) . . ? C10A C11A C12A 115.5(4) . . ? N7A C11A S2A' 116.7(3) . . ? C10A C11A S2A' 97.8(3) . . ? C12A C11A S2A' 110.8(3) . . ? N7A C11A S2A 108.3(3) . . ? C10A C11A S2A 114.1(3) . . ? C12A C11A S2A 103.4(3) . . ? S2A' C11A S2A 16.50(14) . . ? O12A C12A N1A 125.1(4) . . ? O12A C12A C11A 124.0(4) . . ? N1A C12A C11A 110.9(4) . . ? O3A C13A C14A 108.7(4) . . ? O3A C13A H13A 110.0 . . ? C14A C13A H13A 110.0 . . ? O3A C13A H13B 110.0 . . ? C14A C13A H13B 110.0 . . ? H13A C13A H13B 108.3 . . ? C15A C14A C19A 118.4(5) . . ? C15A C14A C13A 120.8(5) . . ? C19A C14A C13A 120.8(5) . . ? C14A C15A C16A 121.5(5) . . ? C14A C15A H15A 119.2 . . ? C16A C15A H15A 119.2 . . ? C15A C16A C17A 119.7(5) . . ? C15A C16A H16A 120.2 . . ? C17A C16A H16A 120.2 . . ? C18A C17A C16A 119.5(5) . . ? C18A C17A H17A 120.2 . . ? C16A C17A H17A 120.2 . . ? C17A C18A C19A 120.7(5) . . ? C17A C18A H18A 119.6 . . ? C19A C18A H18A 119.6 . . ? C18A C19A C14A 120.1(5) . . ? C18A C19A H19A 120.0 . . ? C14A C19A H19A 120.0 . . ? O9A C20A C21A 109.0(5) . . ? O9A C20A H20A 109.9 . . ? C21A C20A H20A 109.9 . . ? O9A C20A H20B 109.9 . . ? C21A C20A H20B 109.9 . . ? H20A C20A H20B 108.3 . . ? C22A C21A C26A 119.2(5) . . ? C22A C21A C20A 122.0(6) . . ? C26A C21A C20A 118.7(6) . . ? C21A C22A C23A 120.8(6) . . ? C21A C22A H22A 119.6 . . ? C23A C22A H22A 119.6 . . ? C24A C23A C22A 119.9(6) . . ? C24A C23A H23A 120.0 . . ? C22A C23A H23A 120.0 . . ? C25A C24A C23A 119.7(6) . . ? C25A C24A H24A 120.2 . . ? C23A C24A H24A 120.2 . . ? C24A C25A C26A 120.9(7) . . ? C24A C25A H25A 119.6 . . ? C26A C25A H25A 119.6 . . ? C25A C26A C21A 119.5(6) . . ? C25A C26A H26A 120.3 . . ? C21A C26A H26A 120.3 . . ? C5B S1B S2B 97.38(14) . . ? C11B S2B S1B 97.57(14) . . ? C12B N1B C5B 120.6(4) . . ? C12B N1B C2B 126.5(4) . . ? C5B N1B C2B 112.9(4) . . ? N1B C2B C3B 103.1(4) . . ? N1B C2B H2B1 111.1 . . ? C3B C2B H2B1 111.1 . . ? N1B C2B H2B2 111.1 . . ? C3B C2B H2B2 111.1 . . ? H2B1 C2B H2B2 109.1 . . ? O3B C3B C2B 107.2(4) . . ? O3B C3B C4B 111.6(4) . . ? C2B C3B C4B 104.4(4) . . ? O3B C3B H3B 111.1 . . ? C2B C3B H3B 111.1 . . ? C4B C3B H3B 111.1 . . ? C13B O3B C3B 113.7(3) . . ? C3B C4B C5B 103.7(3) . . ? C3B C4B H4B1 111.0 . . ? C5B C4B H4B1 111.0 . . ? C3B C4B H4B2 111.0 . . ? C5B C4B H4B2 111.0 . . ? H4B1 C4B H4B2 109.0 . . ? N1B C5B C4B 104.3(4) . . ? N1B C5B C6B 110.8(3) . . ? C4B C5B C6B 116.1(4) . . ? N1B C5B S1B 112.2(3) . . ? C4B C5B S1B 111.5(3) . . ? C6B C5B S1B 102.2(3) . . ? O6B C6B N7B 125.2(4) . . ? O6B C6B C5B 123.8(4) . . ? N7B C6B C5B 111.0(4) . . ? C6B N7B C11B 119.8(4) . . ? C6B N7B C8B 126.1(4) . . ? C11B N7B C8B 114.0(4) . . ? N7B C8B C9B 103.9(4) . . ? N7B C8B H8B1 111.0 . . ? C9B C8B H8B1 111.0 . . ? N7B C8B H8B2 111.0 . . ? C9B C8B H8B2 111.0 . . ? H8B1 C8B H8B2 109.0 . . ? O9B C9B C8B 112.6(4) . . ? O9B C9B C10B 106.8(4) . . ? C8B C9B C10B 104.4(4) . . ? O9B C9B H9B 110.9 . . ? C8B C9B H9B 110.9 . . ? C10B C9B H9B 110.9 . . ? C9B O9B C20B 114.6(4) . . ? C11B C10B C9B 104.8(4) . . ? C11B C10B H10C 110.8 . . ? C9B C10B H10C 110.8 . . ? C11B C10B H10D 110.8 . . ? C9B C10B H10D 110.8 . . ? H10C C10B H10D 108.9 . . ? N7B C11B C12B 111.0(3) . . ? N7B C11B C10B 104.0(3) . . ? C12B C11B C10B 116.6(3) . . ? N7B C11B S2B 111.0(3) . . ? C12B C11B S2B 103.5(3) . . ? C10B C11B S2B 110.8(3) . . ? O12B C12B N1B 125.1(4) . . ? O12B C12B C11B 124.1(4) . . ? N1B C12B C11B 110.8(4) . . ? O3B C13B C14B 106.0(4) . . ? O3B C13B H13C 110.5 . . ? C14B C13B H13C 110.5 . . ? O3B C13B H13D 110.5 . . ? C14B C13B H13D 110.5 . . ? H13C C13B H13D 108.7 . . ? C19B C14B C15B 119.6(5) . . ? C19B C14B C13B 119.5(5) . . ? C15B C14B C13B 120.7(4) . . ? C14B C15B C16B 120.8(5) . . ? C14B C15B H15B 119.6 . . ? C16B C15B H15B 119.6 . . ? C17B C16B C15B 119.3(5) . . ? C17B C16B H16B 120.3 . . ? C15B C16B H16B 120.3 . . ? C18B C17B C16B 120.7(5) . . ? C18B C17B H17B 119.7 . . ? C16B C17B H17B 119.7 . . ? C17B C18B C19B 119.5(5) . . ? C17B C18B H18B 120.3 . . ? C19B C18B H18B 120.3 . . ? C14B C19B C18B 120.1(5) . . ? C14B C19B H19B 120.0 . . ? C18B C19B H19B 120.0 . . ? O9B C20B C21B 108.7(4) . . ? O9B C20B H20C 110.0 . . ? C21B C20B H20C 110.0 . . ? O9B C20B H20D 110.0 . . ? C21B C20B H20D 110.0 . . ? H20C C20B H20D 108.3 . . ? C26B C21B C22B 118.3(5) . . ? C26B C21B C20B 121.3(5) . . ? C22B C21B C20B 120.4(5) . . ? C23B C22B C21B 121.0(5) . . ? C23B C22B H22B 119.5 . . ? C21B C22B H22B 119.5 . . ? C24B C23B C22B 120.5(6) . . ? C24B C23B H23B 119.7 . . ? C22B C23B H23B 119.7 . . ? C23B C24B C25B 119.0(6) . . ? C23B C24B H24B 120.5 . . ? C25B C24B H24B 120.5 . . ? C26B C25B C24B 120.6(6) . . ? C26B C25B H25B 119.7 . . ? C24B C25B H25B 119.7 . . ? C21B C26B C25B 120.5(5) . . ? C21B C26B H26B 119.7 . . ? C25B C26B H26B 119.7 . . ? C5C S1C S2C 97.65(15) . . ? C11C S2C S1C 97.77(15) . . ? C12C N1C C5C 120.2(4) . . ? C12C N1C C2C 126.4(4) . . ? C5C N1C C2C 113.3(4) . . ? N1C C2C C3C 102.9(4) . . ? N1C C2C H2C1 111.2 . . ? C3C C2C H2C1 111.2 . . ? N1C C2C H2C2 111.2 . . ? C3C C2C H2C2 111.2 . . ? H2C1 C2C H2C2 109.1 . . ? O3C C3C C2C 111.5(4) . . ? O3C C3C C4C 108.1(4) . . ? C2C C3C C4C 104.3(4) . . ? O3C C3C H3C 110.9 . . ? C2C C3C H3C 110.9 . . ? C4C C3C H3C 110.9 . . ? C13C O3C C3C 110.7(3) . . ? C5C C4C C3C 104.2(4) . . ? C5C C4C H4C1 110.9 . . ? C3C C4C H4C1 110.9 . . ? C5C C4C H4C2 110.9 . . ? C3C C4C H4C2 110.9 . . ? H4C1 C4C H4C2 108.9 . . ? N1C C5C C4C 104.5(3) . . ? N1C C5C C6C 111.8(3) . . ? C4C C5C C6C 116.2(4) . . ? N1C C5C S1C 111.5(3) . . ? C4C C5C S1C 110.4(3) . . ? C6C C5C S1C 102.5(3) . . ? O6C C6C N7C 125.0(4) . . ? O6C C6C C5C 124.9(4) . . ? N7C C6C C5C 110.1(4) . . ? C6C N7C C11C 119.8(4) . . ? C6C N7C C8C 125.7(4) . . ? C11C N7C C8C 113.9(4) . . ? N7C C8C C9C 104.1(4) . . ? N7C C8C H8C1 110.9 . . ? C9C C8C H8C1 110.9 . . ? N7C C8C H8C2 110.9 . . ? C9C C8C H8C2 110.9 . . ? H8C1 C8C H8C2 109.0 . . ? O9C C9C C8C 107.9(4) . . ? O9C C9C C10C 111.8(4) . . ? C8C C9C C10C 104.4(4) . . ? O9C C9C H9C 110.9 . . ? C8C C9C H9C 110.9 . . ? C10C C9C H9C 110.9 . . ? C9C O9C C20C 111.3(4) . . ? C11C C10C C9C 104.4(4) . . ? C11C C10C H10E 110.9 . . ? C9C C10C H10E 110.9 . . ? C11C C10C H10F 110.9 . . ? C9C C10C H10F 110.9 . . ? H10E C10C H10F 108.9 . . ? N7C C11C C12C 110.7(3) . . ? N7C C11C C10C 104.1(3) . . ? C12C C11C C10C 115.7(4) . . ? N7C C11C S2C 111.5(3) . . ? C12C C11C S2C 104.8(3) . . ? C10C C11C S2C 110.3(3) . . ? O12C C12C N1C 125.2(4) . . ? O12C C12C C11C 124.2(4) . . ? N1C C12C C11C 110.6(4) . . ? O3C C13C C14C 111.0(4) . . ? O3C C13C H13E 109.4 . . ? C14C C13C H13E 109.4 . . ? O3C C13C H13F 109.4 . . ? C14C C13C H13F 109.4 . . ? H13E C13C H13F 108.0 . . ? C19C C14C C15C 118.4(5) . . ? C19C C14C C13C 118.2(4) . . ? C15C C14C C13C 123.4(4) . . ? C16C C15C C14C 120.4(5) . . ? C16C C15C H15C 119.8 . . ? C14C C15C H15C 119.8 . . ? C15C C16C C17C 121.3(5) . . ? C15C C16C H16C 119.3 . . ? C17C C16C H16C 119.3 . . ? C18C C17C C16C 118.2(5) . . ? C18C C17C H17C 120.9 . . ? C16C C17C H17C 120.9 . . ? C17C C18C C19C 121.2(5) . . ? C17C C18C H18C 119.4 . . ? C19C C18C H18C 119.4 . . ? C18C C19C C14C 120.3(5) . . ? C18C C19C H19C 119.8 . . ? C14C C19C H19C 119.8 . . ? O9C C20C C21C 110.3(4) . . ? O9C C20C H20E 109.6 . . ? C21C C20C H20E 109.6 . . ? O9C C20C H20F 109.6 . . ? C21C C20C H20F 109.6 . . ? H20E C20C H20F 108.1 . . ? C26C C21C C22C 119.7(5) . . ? C26C C21C C20C 120.4(5) . . ? C22C C21C C20C 119.8(5) . . ? C23C C22C C21C 119.7(6) . . ? C23C C22C H22C 120.1 . . ? C21C C22C H22C 120.1 . . ? C22C C23C C24C 119.9(7) . . ? C22C C23C H23C 120.1 . . ? C24C C23C H23C 120.0 . . ? C25C C24C C23C 120.1(6) . . ? C25C C24C H24C 119.9 . . ? C23C C24C H24C 119.9 . . ? C24C C25C C26C 119.9(7) . . ? C24C C25C H25C 120.0 . . ? C26C C25C H25C 120.0 . . ? C25C C26C C21C 120.5(7) . . ? C25C C26C H26C 119.8 . . ? C21C C26C H26C 119.8 . . ? Cl2 C1S Cl3 109.7(4) . . ? Cl2 C1S Cl1 112.3(4) . . ? Cl3 C1S Cl1 110.5(4) . . ? Cl2 C1S H1S 108.1 . . ? Cl3 C1S H1S 108.1 . . ? Cl1 C1S H1S 108.1 . . ? Cl3' C1S' Cl1' 110.7(5) . . ? Cl3' C1S' Cl2' 111.8(5) . . ? Cl1' C1S' Cl2' 107.1(4) . . ? Cl3' C1S' H1S' 109.1 . . ? Cl1' C1S' H1S' 109.1 . . ? Cl2' C1S' H1S' 109.1 . . ? Cl4 C2S Cl6 111.1(4) . . ? Cl4 C2S Cl5 110.1(4) . . ? Cl6 C2S Cl5 110.7(4) . . ? Cl4 C2S H2S 108.3 . . ? Cl6 C2S H2S 108.3 . . ? Cl5 C2S H2S 108.3 . . ? Cl5' C2S' Cl4' 112.4(6) . . ? Cl5' C2S' Cl6' 109.8(6) . . ? Cl4' C2S' Cl6' 106.6(6) . . ? Cl5' C2S' H2S' 109.3 . . ? Cl4' C2S' H2S' 109.3 . . ? Cl6' C2S' H2S' 109.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5A S1A S2A C11A -11.4(2) . . . . ? C11A S2A' S3A' S1A' -66.3(3) . . . . ? C5A S1A' S3A' S2A' 62.7(3) . . . . ? C12A N1A C2A C3A -174.1(4) . . . . ? C5A N1A C2A C3A 10.5(5) . . . . ? N1A C2A C3A O3A 86.8(5) . . . . ? N1A C2A C3A C4A -27.3(5) . . . . ? C4A C3A O3A C13A -167.8(4) . . . . ? C2A C3A O3A C13A 79.3(5) . . . . ? O3A C3A C4A C5A -84.3(4) . . . . ? C2A C3A C4A C5A 34.7(5) . . . . ? C12A N1A C5A C4A -164.8(4) . . . . ? C2A N1A C5A C4A 10.7(5) . . . . ? C12A N1A C5A C6A -39.1(5) . . . . ? C2A N1A C5A C6A 136.4(4) . . . . ? C12A N1A C5A S1A 70.7(5) . . . . ? C2A N1A C5A S1A -113.8(4) . . . . ? C12A N1A C5A S1A' 87.5(5) . . . . ? C2A N1A C5A S1A' -97.0(4) . . . . ? C3A C4A C5A N1A -28.0(5) . . . . ? C3A C4A C5A C6A -150.9(4) . . . . ? C3A C4A C5A S1A 91.3(4) . . . . ? C3A C4A C5A S1A' 88.5(4) . . . . ? S2A S1A C5A N1A -48.4(4) . . . . ? S2A S1A C5A C4A -165.2(3) . . . . ? S2A S1A C5A C6A 68.7(3) . . . . ? S2A S1A C5A S1A' -155.3(6) . . . . ? S3A' S1A' C5A N1A -95.2(4) . . . . ? S3A' S1A' C5A C4A 154.9(4) . . . . ? S3A' S1A' C5A C6A 31.3(4) . . . . ? S3A' S1A' C5A S1A -16.2(4) . . . . ? N1A C5A C6A O6A -143.6(4) . . . . ? C4A C5A C6A O6A -24.9(6) . . . . ? S1A C5A C6A O6A 101.5(5) . . . . ? S1A' C5A C6A O6A 89.4(5) . . . . ? N1A C5A C6A N7A 39.8(5) . . . . ? C4A C5A C6A N7A 158.6(4) . . . . ? S1A C5A C6A N7A -75.1(4) . . . . ? S1A' C5A C6A N7A -87.1(4) . . . . ? O6A C6A N7A C11A -173.7(4) . . . . ? C5A C6A N7A C11A 2.7(6) . . . . ? O6A C6A N7A C8A -1.5(8) . . . . ? C5A C6A N7A C8A 175.0(4) . . . . ? C6A N7A C8A C9A -169.2(4) . . . . ? C11A N7A C8A C9A 3.6(5) . . . . ? N7A C8A C9A O9A 101.7(5) . . . . ? N7A C8A C9A C10A -20.1(5) . . . . ? C8A C9A O9A C20A 174.1(5) . . . . ? C10A C9A O9A C20A -70.0(6) . . . . ? O9A C9A C10A C11A -88.9(5) . . . . ? C8A C9A C10A C11A 29.1(5) . . . . ? C6A N7A C11A C10A -172.1(4) . . . . ? C8A N7A C11A C10A 14.6(5) . . . . ? C6A N7A C11A C12A -47.0(5) . . . . ? C8A N7A C11A C12A 139.8(4) . . . . ? C6A N7A C11A S2A' 81.3(5) . . . . ? C8A N7A C11A S2A' -92.0(5) . . . . ? C6A N7A C11A S2A 65.9(5) . . . . ? C8A N7A C11A S2A -107.4(4) . . . . ? C9A C10A C11A N7A -26.8(5) . . . . ? C9A C10A C11A C12A -149.1(4) . . . . ? C9A C10A C11A S2A' 93.4(4) . . . . ? C9A C10A C11A S2A 91.3(4) . . . . ? S3A' S2A' C11A N7A -23.1(5) . . . . ? S3A' S2A' C11A C10A -133.5(3) . . . . ? S3A' S2A' C11A C12A 105.4(4) . . . . ? S3A' S2A' C11A S2A 39.6(5) . . . . ? S1A S2A C11A N7A -49.2(3) . . . . ? S1A S2A C11A C10A -165.0(3) . . . . ? S1A S2A C11A C12A 68.7(3) . . . . ? S1A S2A C11A S2A' -172.5(6) . . . . ? C5A N1A C12A O12A 176.3(4) . . . . ? C2A N1A C12A O12A 1.4(7) . . . . ? C5A N1A C12A C11A -4.3(5) . . . . ? C2A N1A C12A C11A -179.3(4) . . . . ? N7A C11A C12A O12A -133.7(4) . . . . ? C10A C11A C12A O12A -15.1(6) . . . . ? S2A' C11A C12A O12A 94.9(5) . . . . ? S2A C11A C12A O12A 110.3(4) . . . . ? N7A C11A C12A N1A 46.9(5) . . . . ? C10A C11A C12A N1A 165.6(4) . . . . ? S2A' C11A C12A N1A -84.4(4) . . . . ? S2A C11A C12A N1A -69.0(4) . . . . ? C3A O3A C13A C14A 177.9(4) . . . . ? O3A C13A C14A C15A 98.6(6) . . . . ? O3A C13A C14A C19A -81.8(6) . . . . ? C19A C14A C15A C16A -0.5(8) . . . . ? C13A C14A C15A C16A 179.1(5) . . . . ? C14A C15A C16A C17A -0.3(9) . . . . ? C15A C16A C17A C18A 0.3(9) . . . . ? C16A C17A C18A C19A 0.6(8) . . . . ? C17A C18A C19A C14A -1.5(8) . . . . ? C15A C14A C19A C18A 1.5(8) . . . . ? C13A C14A C19A C18A -178.2(5) . . . . ? C9A O9A C20A C21A -158.9(5) . . . . ? O9A C20A C21A C22A -57.1(8) . . . . ? O9A C20A C21A C26A 124.4(7) . . . . ? C26A C21A C22A C23A 1.2(9) . . . . ? C20A C21A C22A C23A -177.4(6) . . . . ? C21A C22A C23A C24A -1.2(10) . . . . ? C22A C23A C24A C25A 2.3(11) . . . . ? C23A C24A C25A C26A -3.2(13) . . . . ? C24A C25A C26A C21A 3.2(12) . . . . ? C22A C21A C26A C25A -2.1(10) . . . . ? C20A C21A C26A C25A 176.5(7) . . . . ? C5B S1B S2B C11B -15.3(2) . . . . ? C12B N1B C2B C3B -169.2(4) . . . . ? C5B N1B C2B C3B 11.4(5) . . . . ? N1B C2B C3B O3B 90.4(4) . . . . ? N1B C2B C3B C4B -28.1(4) . . . . ? C2B C3B O3B C13B 165.3(4) . . . . ? C4B C3B O3B C13B -81.0(5) . . . . ? O3B C3B C4B C5B -81.0(4) . . . . ? C2B C3B C4B C5B 34.5(4) . . . . ? C12B N1B C5B C4B -169.4(4) . . . . ? C2B N1B C5B C4B 10.0(4) . . . . ? C12B N1B C5B C6B -43.8(5) . . . . ? C2B N1B C5B C6B 135.6(4) . . . . ? C12B N1B C5B S1B 69.7(5) . . . . ? C2B N1B C5B S1B -110.8(3) . . . . ? C3B C4B C5B N1B -27.2(4) . . . . ? C3B C4B C5B C6B -149.4(3) . . . . ? C3B C4B C5B S1B 94.1(4) . . . . ? S2B S1B C5B N1B -45.6(3) . . . . ? S2B S1B C5B C4B -162.2(3) . . . . ? S2B S1B C5B C6B 73.1(3) . . . . ? N1B C5B C6B O6B -136.3(4) . . . . ? C4B C5B C6B O6B -17.6(6) . . . . ? S1B C5B C6B O6B 103.9(4) . . . . ? N1B C5B C6B N7B 46.3(5) . . . . ? C4B C5B C6B N7B 165.0(4) . . . . ? S1B C5B C6B N7B -73.5(4) . . . . ? O6B C6B N7B C11B -179.5(4) . . . . ? C5B C6B N7B C11B -2.2(5) . . . . ? O6B C6B N7B C8B -3.6(7) . . . . ? C5B C6B N7B C8B 173.7(4) . . . . ? C6B N7B C8B C9B -169.3(4) . . . . ? C11B N7B C8B C9B 6.8(5) . . . . ? N7B C8B C9B O9B 92.9(4) . . . . ? N7B C8B C9B C10B -22.6(4) . . . . ? C8B C9B O9B C20B 73.4(5) . . . . ? C10B C9B O9B C20B -172.6(4) . . . . ? O9B C9B C10B C11B -89.4(4) . . . . ? C8B C9B C10B C11B 30.1(4) . . . . ? C6B N7B C11B C12B -45.4(5) . . . . ? C8B N7B C11B C12B 138.2(4) . . . . ? C6B N7B C11B C10B -171.6(4) . . . . ? C8B N7B C11B C10B 12.0(5) . . . . ? C6B N7B C11B S2B 69.2(5) . . . . ? C8B N7B C11B S2B -107.2(4) . . . . ? C9B C10B C11B N7B -25.7(4) . . . . ? C9B C10B C11B C12B -148.3(4) . . . . ? C9B C10B C11B S2B 93.6(4) . . . . ? S1B S2B C11B N7B -46.6(3) . . . . ? S1B S2B C11B C12B 72.5(3) . . . . ? S1B S2B C11B C10B -161.7(3) . . . . ? C5B N1B C12B O12B 177.7(4) . . . . ? C2B N1B C12B O12B -1.6(7) . . . . ? C5B N1B C12B C11B -3.4(5) . . . . ? C2B N1B C12B C11B 177.2(4) . . . . ? N7B C11B C12B O12B -133.1(4) . . . . ? C10B C11B C12B O12B -14.3(6) . . . . ? S2B C11B C12B O12B 107.7(4) . . . . ? N7B C11B C12B N1B 48.0(5) . . . . ? C10B C11B C12B N1B 166.9(4) . . . . ? S2B C11B C12B N1B -71.2(4) . . . . ? C3B O3B C13B C14B 169.7(4) . . . . ? O3B C13B C14B C19B -110.9(5) . . . . ? O3B C13B C14B C15B 64.6(6) . . . . ? C19B C14B C15B C16B 2.5(7) . . . . ? C13B C14B C15B C16B -173.0(5) . . . . ? C14B C15B C16B C17B -1.7(8) . . . . ? C15B C16B C17B C18B -0.5(9) . . . . ? C16B C17B C18B C19B 1.8(9) . . . . ? C15B C14B C19B C18B -1.1(8) . . . . ? C13B C14B C19B C18B 174.4(5) . . . . ? C17B C18B C19B C14B -1.0(9) . . . . ? C9B O9B C20B C21B -142.7(4) . . . . ? O9B C20B C21B C26B 34.4(7) . . . . ? O9B C20B C21B C22B -148.1(5) . . . . ? C26B C21B C22B C23B -1.7(9) . . . . ? C20B C21B C22B C23B -179.3(6) . . . . ? C21B C22B C23B C24B 1.4(10) . . . . ? C22B C23B C24B C25B -0.5(10) . . . . ? C23B C24B C25B C26B 0.0(10) . . . . ? C22B C21B C26B C25B 1.2(9) . . . . ? C20B C21B C26B C25B 178.8(5) . . . . ? C24B C25B C26B C21B -0.4(10) . . . . ? C5C S1C S2C C11C -12.3(2) . . . . ? C12C N1C C2C C3C -168.8(4) . . . . ? C5C N1C C2C C3C 15.8(5) . . . . ? N1C C2C C3C O3C 87.1(4) . . . . ? N1C C2C C3C C4C -29.4(4) . . . . ? C2C C3C O3C C13C 81.8(5) . . . . ? C4C C3C O3C C13C -164.1(4) . . . . ? O3C C3C C4C C5C -86.1(4) . . . . ? C2C C3C C4C C5C 32.8(5) . . . . ? C12C N1C C5C C4C -171.1(4) . . . . ? C2C N1C C5C C4C 4.6(5) . . . . ? C12C N1C C5C C6C -44.6(5) . . . . ? C2C N1C C5C C6C 131.1(4) . . . . ? C12C N1C C5C S1C 69.5(4) . . . . ? C2C N1C C5C S1C -114.7(3) . . . . ? C3C C4C C5C N1C -23.0(4) . . . . ? C3C C4C C5C C6C -146.7(4) . . . . ? C3C C4C C5C S1C 97.1(4) . . . . ? S2C S1C C5C N1C -48.4(3) . . . . ? S2C S1C C5C C4C -164.2(3) . . . . ? S2C S1C C5C C6C 71.3(3) . . . . ? N1C C5C C6C O6C -137.6(4) . . . . ? C4C C5C C6C O6C -17.7(6) . . . . ? S1C C5C C6C O6C 102.9(5) . . . . ? N1C C5C C6C N7C 44.2(5) . . . . ? C4C C5C C6C N7C 164.0(4) . . . . ? S1C C5C C6C N7C -75.4(4) . . . . ? O6C C6C N7C C11C -176.3(4) . . . . ? C5C C6C N7C C11C 1.9(5) . . . . ? O6C C6C N7C C8C -5.4(7) . . . . ? C5C C6C N7C C8C 172.9(4) . . . . ? C6C N7C C8C C9C -166.7(4) . . . . ? C11C N7C C8C C9C 4.8(5) . . . . ? N7C C8C C9C O9C 97.6(4) . . . . ? N7C C8C C9C C10C -21.5(5) . . . . ? C8C C9C O9C C20C 164.0(4) . . . . ? C10C C9C O9C C20C -81.8(5) . . . . ? O9C C9C C10C C11C -86.2(4) . . . . ? C8C C9C C10C C11C 30.1(5) . . . . ? C6C N7C C11C C12C -48.8(5) . . . . ? C8C N7C C11C C12C 139.2(4) . . . . ? C6C N7C C11C C10C -173.8(4) . . . . ? C8C N7C C11C C10C 14.2(5) . . . . ? C6C N7C C11C S2C 67.4(5) . . . . ? C8C N7C C11C S2C -104.6(4) . . . . ? C9C C10C C11C N7C -27.0(4) . . . . ? C9C C10C C11C C12C -148.6(4) . . . . ? C9C C10C C11C S2C 92.7(4) . . . . ? S1C S2C C11C N7C -49.2(3) . . . . ? S1C S2C C11C C12C 70.6(3) . . . . ? S1C S2C C11C C10C -164.3(3) . . . . ? C5C N1C C12C O12C 178.6(4) . . . . ? C2C N1C C12C O12C 3.5(7) . . . . ? C5C N1C C12C C11C -2.4(5) . . . . ? C2C N1C C12C C11C -177.5(4) . . . . ? N7C C11C C12C O12C -132.6(4) . . . . ? C10C C11C C12C O12C -14.6(6) . . . . ? S2C C11C C12C O12C 107.0(4) . . . . ? N7C C11C C12C N1C 48.4(4) . . . . ? C10C C11C C12C N1C 166.4(4) . . . . ? S2C C11C C12C N1C -71.9(4) . . . . ? C3C O3C C13C C14C -175.4(4) . . . . ? O3C C13C C14C C19C -174.0(5) . . . . ? O3C C13C C14C C15C 5.9(7) . . . . ? C19C C14C C15C C16C -1.3(8) . . . . ? C13C C14C C15C C16C 178.8(5) . . . . ? C14C C15C C16C C17C 2.3(9) . . . . ? C15C C16C C17C C18C -2.0(10) . . . . ? C16C C17C C18C C19C 0.7(10) . . . . ? C17C C18C C19C C14C 0.2(10) . . . . ? C15C C14C C19C C18C 0.1(9) . . . . ? C13C C14C C19C C18C 180.0(6) . . . . ? C9C O9C C20C C21C 171.1(4) . . . . ? O9C C20C C21C C26C 122.3(5) . . . . ? O9C C20C C21C C22C -60.3(6) . . . . ? C26C C21C C22C C23C 1.0(7) . . . . ? C20C C21C C22C C23C -176.5(5) . . . . ? C21C C22C C23C C24C 1.7(9) . . . . ? C22C C23C C24C C25C -3.3(10) . . . . ? C23C C24C C25C C26C 2.2(10) . . . . ? C24C C25C C26C C21C 0.5(9) . . . . ? C22C C21C C26C C25C -2.1(8) . . . . ? C20C C21C C26C C25C 175.4(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 1.816 _refine_diff_density_min -1.324 _refine_diff_density_rms 0.091 #============================================================================== #_eof # End of Crystallographic Information File