# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Ward, Michael' 'Soegiarto, Airon' 'Yan, Wah' 'Kent, Andrew' _publ_contact_author_name 'Ward, Michael' _publ_contact_author_email mdw3@nyu.edu _publ_section_title ; Regulating Low-Dimensional Magnetic Behavior of Organic Radicals in Crystalline Hydrogen-Bonded Host Frameworks ; # Attachment '- GDS 1.cif' data_GDS_1 _database_code_depnum_ccdc_archive 'CCDC 802079' #TrackingRef '- GDS 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H54 N8 O8 S2' _chemical_formula_weight 718.93 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 Pbca 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' '-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 12.7246(8) _cell_length_b 12.4100(8) _cell_length_c 24.2921(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3836.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9486 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 28.51 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.245 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1544 _exptl_absorpt_coefficient_mu 0.194 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9300 _exptl_absorpt_correction_T_max 0.9495 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 126264 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0087 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.63 _reflns_number_total 4906 _reflns_number_gt 4379 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+1.4102P] 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 4906 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0389 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0994 _refine_ls_wR_factor_gt 0.0941 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _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 S1 S 0.07662(2) 0.51647(2) 0.170205(10) 0.01950(8) Uani 1 1 d . . . C2 C 0.05435(8) 0.49399(8) 0.09934(4) 0.01977(19) Uani 1 1 d . . . C4 C 0.07407(9) 0.38950(9) 0.07822(5) 0.0267(2) Uani 1 1 d . . . H4 H 0.1023 0.3351 0.1014 0.032 Uiso 1 1 calc R . . C1 C 0.15222(9) 0.19512(9) 0.23058(4) 0.0234(2) Uani 1 1 d . . . C3 C 0.01417(8) 0.57415(8) 0.06685(4) 0.0210(2) Uani 1 1 d . . . H3 H 0.0022 0.6439 0.0817 0.025 Uiso 1 1 calc R . . C7 C 0.68860(9) 0.44476(10) 0.10104(5) 0.0292(2) Uani 1 1 d . . . C5 C -0.00949(8) 0.55241(8) 0.01070(4) 0.0200(2) Uani 1 1 d . . . C11 C 0.48234(9) 0.46903(10) 0.10180(5) 0.0299(2) Uani 1 1 d . . . C6 C 0.05231(10) 0.36716(9) 0.02417(5) 0.0270(2) Uani 1 1 d . . . H6 H 0.0660 0.2973 0.0099 0.032 Uiso 1 1 calc R . . C13 C 0.44797(10) 0.41741(11) 0.15619(5) 0.0344(3) Uani 1 1 d . . . H13A H 0.4487 0.3388 0.1524 0.052 Uiso 1 1 calc R . . H13B H 0.3767 0.4415 0.1654 0.052 Uiso 1 1 calc R . . H13C H 0.4965 0.4390 0.1855 0.052 Uiso 1 1 calc R . . C8 C 0.69607(12) 0.56728(11) 0.10630(7) 0.0448(3) Uani 1 1 d . . . H8A H 0.7621 0.5860 0.1257 0.054 Uiso 1 1 calc R . . H8B H 0.6993 0.5993 0.0690 0.054 Uiso 1 1 calc R . . C14 C 0.76596(11) 0.40423(13) 0.05780(6) 0.0435(3) Uani 1 1 d . . . H14A H 0.7601 0.3257 0.0546 0.065 Uiso 1 1 calc R . . H14B H 0.8377 0.4234 0.0688 0.065 Uiso 1 1 calc R . . H14C H 0.7498 0.4375 0.0222 0.065 Uiso 1 1 calc R . . C15 C 0.71298(12) 0.38912(14) 0.15608(6) 0.0449(3) Uani 1 1 d . . . H15A H 0.6705 0.4218 0.1853 0.067 Uiso 1 1 calc R . . H15B H 0.7877 0.3979 0.1648 0.067 Uiso 1 1 calc R . . H15C H 0.6963 0.3122 0.1533 0.067 Uiso 1 1 calc R . . C10 C 0.50281(13) 0.58964(12) 0.10776(7) 0.0471(4) Uani 1 1 d . . . H10A H 0.5048 0.6225 0.0706 0.056 Uiso 1 1 calc R . . H10B H 0.4435 0.6226 0.1281 0.056 Uiso 1 1 calc R . . C9 C 0.60385(15) 0.61629(12) 0.13734(8) 0.0556(4) Uani 1 1 d . . . H9A H 0.6016 0.5873 0.1753 0.067 Uiso 1 1 calc R . . H9B H 0.6125 0.6954 0.1396 0.067 Uiso 1 1 calc R . . C12 C 0.39683(13) 0.44872(19) 0.05920(7) 0.0581(5) Uani 1 1 d . . . H12A H 0.4200 0.4757 0.0233 0.087 Uiso 1 1 calc R . . H12B H 0.3324 0.4862 0.0702 0.087 Uiso 1 1 calc R . . H12C H 0.3830 0.3712 0.0567 0.087 Uiso 1 1 calc R . . N2 N 0.17122(8) 0.09654(8) 0.24958(4) 0.0289(2) Uani 1 1 d . . . H2A H 0.1246 0.0640 0.2705 0.035 Uiso 1 1 calc R . . H2B H 0.2304 0.0638 0.2412 0.035 Uiso 1 1 calc R . . N4 N 0.58048(7) 0.41477(8) 0.08256(4) 0.0263(2) Uani 1 1 d . . . N1 N 0.06309(8) 0.24435(8) 0.24319(4) 0.0281(2) Uani 1 1 d . . . H1A H 0.0504 0.3095 0.2305 0.034 Uiso 1 1 calc R . . H1B H 0.0165 0.2119 0.2642 0.034 Uiso 1 1 calc R . . N3 N 0.22281(8) 0.24373(8) 0.19881(4) 0.0315(2) Uani 1 1 d . . . H3A H 0.2104 0.3089 0.1861 0.038 Uiso 1 1 calc R . . H3B H 0.2820 0.2108 0.1905 0.038 Uiso 1 1 calc R . . O2 O 0.07400(6) 0.63283(6) 0.17935(3) 0.02502(17) Uani 1 1 d . . . O1 O -0.00721(7) 0.46000(7) 0.19940(3) 0.02736(18) Uani 1 1 d . . . O3 O 0.17976(7) 0.47042(7) 0.18270(3) 0.02795(18) Uani 1 1 d . . . O4 O 0.56982(8) 0.31790(9) 0.06562(5) 0.0496(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 0.02189(14) 0.01948(13) 0.01712(13) -0.00137(8) -0.00063(8) 0.00075(9) C2 0.0222(5) 0.0200(4) 0.0171(4) -0.0019(4) 0.0009(4) -0.0004(4) C4 0.0378(6) 0.0200(5) 0.0222(5) -0.0002(4) -0.0037(4) 0.0058(4) C1 0.0260(5) 0.0233(5) 0.0210(5) -0.0025(4) 0.0004(4) -0.0014(4) C3 0.0255(5) 0.0180(4) 0.0194(5) -0.0024(4) 0.0015(4) 0.0012(4) C7 0.0247(5) 0.0308(6) 0.0322(6) -0.0009(5) 0.0021(4) -0.0049(4) C5 0.0237(5) 0.0177(5) 0.0184(4) -0.0011(4) 0.0018(4) 0.0011(4) C11 0.0258(5) 0.0375(6) 0.0266(5) 0.0026(5) 0.0035(4) 0.0033(5) C6 0.0407(6) 0.0177(5) 0.0225(5) -0.0027(4) -0.0023(4) 0.0062(4) C13 0.0328(6) 0.0403(7) 0.0302(6) 0.0036(5) 0.0094(5) 0.0029(5) C8 0.0461(8) 0.0338(7) 0.0546(8) -0.0053(6) 0.0039(7) -0.0177(6) C14 0.0292(6) 0.0536(8) 0.0477(8) -0.0008(7) 0.0129(6) -0.0003(6) C15 0.0358(7) 0.0585(9) 0.0403(7) 0.0091(7) -0.0030(6) 0.0027(6) C10 0.0562(9) 0.0306(6) 0.0544(9) 0.0083(6) 0.0162(7) 0.0136(6) C9 0.0701(11) 0.0264(6) 0.0704(11) -0.0159(7) 0.0141(9) -0.0096(7) C12 0.0306(7) 0.1073(15) 0.0365(8) 0.0089(9) -0.0049(6) -0.0023(8) N2 0.0292(5) 0.0238(4) 0.0338(5) 0.0039(4) 0.0065(4) 0.0019(4) N4 0.0261(5) 0.0269(5) 0.0260(5) -0.0064(4) 0.0050(4) -0.0052(4) N1 0.0287(5) 0.0245(4) 0.0311(5) 0.0024(4) 0.0078(4) 0.0020(4) N3 0.0283(5) 0.0262(5) 0.0399(6) 0.0062(4) 0.0102(4) 0.0022(4) O2 0.0310(4) 0.0207(4) 0.0234(4) -0.0046(3) -0.0004(3) 0.0010(3) O1 0.0309(4) 0.0280(4) 0.0231(4) 0.0019(3) 0.0055(3) -0.0021(3) O3 0.0261(4) 0.0278(4) 0.0300(4) -0.0034(3) -0.0071(3) 0.0045(3) O4 0.0468(6) 0.0389(5) 0.0630(7) -0.0294(5) 0.0165(5) -0.0157(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4601(8) . ? S1 O2 1.4614(8) . ? S1 O3 1.4632(8) . ? S1 C2 1.7668(10) . ? C2 C3 1.3689(14) . ? C2 C4 1.4169(14) . ? C4 C6 1.3703(15) . ? C4 H4 0.9500 . ? C1 N1 1.3242(14) . ? C1 N3 1.3289(14) . ? C1 N2 1.3297(14) . ? C3 C5 1.4226(14) . ? C3 H3 0.9500 . ? C7 N4 1.4943(15) . ? C7 C14 1.5249(17) . ? C7 C8 1.5288(18) . ? C7 C15 1.5366(19) . ? C5 C6 1.4179(14) 5_565 ? C5 C5 1.4217(19) 5_565 ? C11 N4 1.4938(15) . ? C11 C12 1.523(2) . ? C11 C10 1.5261(19) . ? C11 C13 1.5320(17) . ? C6 C5 1.4179(14) 5_565 ? C6 H6 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C8 C9 1.522(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C10 C9 1.510(3) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N4 O4 1.2779(13) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 112.56(5) . . ? O1 S1 O3 111.54(5) . . ? O2 S1 O3 112.01(5) . . ? O1 S1 C2 106.28(5) . . ? O2 S1 C2 107.49(5) . . ? O3 S1 C2 106.52(5) . . ? C3 C2 C4 121.50(9) . . ? C3 C2 S1 120.46(8) . . ? C4 C2 S1 117.96(8) . . ? C6 C4 C2 119.76(10) . . ? C6 C4 H4 120.1 . . ? C2 C4 H4 120.1 . . ? N1 C1 N3 120.25(10) . . ? N1 C1 N2 119.99(10) . . ? N3 C1 N2 119.76(10) . . ? C2 C3 C5 119.61(9) . . ? C2 C3 H3 120.2 . . ? C5 C3 H3 120.2 . . ? N4 C7 C14 107.78(10) . . ? N4 C7 C8 109.27(11) . . ? C14 C7 C8 110.21(11) . . ? N4 C7 C15 109.59(10) . . ? C14 C7 C15 108.72(11) . . ? C8 C7 C15 111.20(12) . . ? C6 C5 C5 119.39(11) 5_565 5_565 ? C6 C5 C3 121.38(9) 5_565 . ? C5 C5 C3 119.23(11) 5_565 . ? N4 C11 C12 108.06(11) . . ? N4 C11 C10 109.21(10) . . ? C12 C11 C10 110.41(13) . . ? N4 C11 C13 108.66(10) . . ? C12 C11 C13 108.23(11) . . ? C10 C11 C13 112.16(11) . . ? C4 C6 C5 120.51(10) . 5_565 ? C4 C6 H6 119.7 . . ? C5 C6 H6 119.7 5_565 . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C9 C8 C7 113.02(11) . . ? C9 C8 H8A 109.0 . . ? C7 C8 H8A 109.0 . . ? C9 C8 H8B 109.0 . . ? C7 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C7 C14 H14A 109.5 . . ? C7 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C7 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C7 C15 H15A 109.5 . . ? C7 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C7 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C9 C10 C11 113.92(12) . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10B 108.8 . . ? C11 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C9 C8 109.47(13) . . ? C10 C9 H9A 109.8 . . ? C8 C9 H9A 109.8 . . ? C10 C9 H9B 109.8 . . ? C8 C9 H9B 109.8 . . ? H9A C9 H9B 108.2 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? O4 N4 C11 115.86(9) . . ? O4 N4 C7 115.39(10) . . ? C11 N4 C7 124.29(9) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C2 C3 104.98(9) . . . . ? O2 S1 C2 C3 -15.76(10) . . . . ? O3 S1 C2 C3 -135.98(9) . . . . ? O1 S1 C2 C4 -71.76(10) . . . . ? O2 S1 C2 C4 167.51(9) . . . . ? O3 S1 C2 C4 47.29(10) . . . . ? C3 C2 C4 C6 -0.27(18) . . . . ? S1 C2 C4 C6 176.42(9) . . . . ? C4 C2 C3 C5 0.62(16) . . . . ? S1 C2 C3 C5 -176.00(8) . . . . ? C2 C3 C5 C6 179.28(10) . . . 5_565 ? C2 C3 C5 C5 -0.23(18) . . . 5_565 ? C2 C4 C6 C5 -0.46(18) . . . 5_565 ? N4 C7 C8 C9 47.17(17) . . . . ? C14 C7 C8 C9 165.42(14) . . . . ? C15 C7 C8 C9 -73.94(17) . . . . ? N4 C11 C10 C9 -46.18(16) . . . . ? C12 C11 C10 C9 -164.86(13) . . . . ? C13 C11 C10 C9 74.34(16) . . . . ? C11 C10 C9 C8 59.11(18) . . . . ? C7 C8 C9 C10 -59.46(18) . . . . ? C12 C11 N4 O4 -46.80(16) . . . . ? C10 C11 N4 O4 -166.94(12) . . . . ? C13 C11 N4 O4 70.43(14) . . . . ? C12 C11 N4 C7 158.08(12) . . . . ? C10 C11 N4 C7 37.93(15) . . . . ? C13 C11 N4 C7 -84.70(14) . . . . ? C14 C7 N4 O4 46.28(14) . . . . ? C8 C7 N4 O4 166.05(11) . . . . ? C15 C7 N4 O4 -71.87(14) . . . . ? C14 C7 N4 C11 -158.48(11) . . . . ? C8 C7 N4 C11 -38.72(15) . . . . ? C15 C7 N4 C11 83.37(14) . . . . ? 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 N2 H2A O1 0.88 2.10 2.9602(13) 163.9 3_545 N2 H2B O3 0.88 2.16 2.9471(13) 148.5 8_655 N1 H1A O1 0.88 2.14 3.0156(13) 170.5 . N1 H1B O2 0.88 2.04 2.9154(12) 171.8 3_545 N3 H3A O3 0.88 2.04 2.8927(13) 161.7 . N3 H3B O2 0.88 2.09 2.9669(13) 174.2 8_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.63 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.364 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.051 # Attachment '- GDS 2.cif' data_GDS_2 _database_code_depnum_ccdc_archive 'CCDC 802080' #TrackingRef '- GDS 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H56 N8 O8 S2' _chemical_formula_weight 744.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.6700(6) _cell_length_b 9.2621(7) _cell_length_c 29.002(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.1130(10) _cell_angle_gamma 90.00 _cell_volume 2055.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9566 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 28.51 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.204 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.183 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9353 _exptl_absorpt_correction_T_max 0.9695 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 37360 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0117 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4485 _reflns_number_gt 4003 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0514P)^2^+0.7397P] 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 4485 _refine_ls_number_parameters 230 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.1056 _refine_ls_wR_factor_gt 0.1013 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.063 _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 S1 S 0.48604(4) 0.13969(4) 0.177055(11) 0.03088(11) Uani 1 1 d . . . C5 C 0.49870(16) 0.02096(14) 0.02483(4) 0.0288(3) Uani 1 1 d . . . C2 C 0.48865(16) 0.09379(15) 0.11805(4) 0.0289(3) Uani 1 1 d . . . C6 C 0.4143(2) 0.14527(16) 0.03815(5) 0.0419(4) Uani 1 1 d . . . H6 H 0.3596 0.2066 0.0152 0.050 Uiso 1 1 calc R . . C7 C 0.4087(2) 0.18130(16) 0.08449(5) 0.0415(3) Uani 1 1 d . . . H7 H 0.3496 0.2663 0.0930 0.050 Uiso 1 1 calc R . . C1 C 0.99892(18) -0.00562(17) 0.22701(5) 0.0374(3) Uani 1 1 d . . . C4 C 0.5792(2) -0.06570(17) 0.05937(5) 0.0420(4) Uani 1 1 d . . . H4 H 0.6379 -0.1512 0.0511 0.050 Uiso 1 1 calc R . . C3 C 0.5749(2) -0.02918(17) 0.10572(5) 0.0426(4) Uani 1 1 d . . . H3 H 0.6314 -0.0889 0.1289 0.051 Uiso 1 1 calc R . . C8 C 1.0810(2) 0.71179(19) 0.07694(6) 0.0491(4) Uani 1 1 d . . . C12 C 0.8577(2) 0.53415(19) 0.11279(7) 0.0525(4) Uani 1 1 d . . . C15 C 0.6598(3) 0.5399(3) 0.11483(10) 0.0846(8) Uani 1 1 d . . . H15A H 0.6245 0.6381 0.1226 0.127 Uiso 1 1 calc R . . H15B H 0.6242 0.4726 0.1385 0.127 Uiso 1 1 calc R . . H15C H 0.6034 0.5127 0.0847 0.127 Uiso 1 1 calc R . . C10 C 1.1364(4) 0.6134(3) 0.15828(8) 0.0913(8) Uani 1 1 d . . . H10A H 1.1868 0.6382 0.1897 0.110 Uiso 1 1 calc R . . H10B H 1.2020 0.5302 0.1469 0.110 Uiso 1 1 calc R . . C14 C 1.2025(3) 0.6129(3) 0.05143(8) 0.0704(6) Uani 1 1 d . . . H14A H 1.2345 0.5289 0.0708 0.106 Uiso 1 1 calc R . . H14B H 1.3083 0.6662 0.0449 0.106 Uiso 1 1 calc R . . H14C H 1.1423 0.5805 0.0223 0.106 Uiso 1 1 calc R . . C16 C 0.9102(3) 0.3828(2) 0.09764(8) 0.0665(5) Uani 1 1 d . . . H16A H 0.8731 0.3689 0.0649 0.100 Uiso 1 1 calc R . . H16B H 0.8538 0.3104 0.1162 0.100 Uiso 1 1 calc R . . H16C H 1.0374 0.3722 0.1021 0.100 Uiso 1 1 calc R . . C13 C 1.0567(3) 0.8539(2) 0.05087(10) 0.0767(7) Uani 1 1 d . . . H13A H 1.0179 0.8343 0.0185 0.115 Uiso 1 1 calc R . . H13B H 1.1679 0.9063 0.0522 0.115 Uiso 1 1 calc R . . H13C H 0.9686 0.9124 0.0651 0.115 Uiso 1 1 calc R . . C11 C 0.9463(4) 0.5744(3) 0.15998(8) 0.0820(7) Uani 1 1 d . . . H11A H 0.8835 0.6573 0.1726 0.098 Uiso 1 1 calc R . . H11B H 0.9363 0.4920 0.1814 0.098 Uiso 1 1 calc R . . C9 C 1.1519(3) 0.7405(3) 0.12642(8) 0.0756(6) Uani 1 1 d . . . H9A H 1.2766 0.7682 0.1263 0.091 Uiso 1 1 calc R . . H9B H 1.0881 0.8234 0.1387 0.091 Uiso 1 1 calc R . . N4 N 0.90637(17) 0.64180(14) 0.07744(5) 0.0414(3) Uani 1 1 d . . . N3 N 1.15025(16) -0.06254(15) 0.24240(4) 0.0436(3) Uani 1 1 d . . . H3A H 1.1532 -0.1312 0.2634 0.052 Uiso 1 1 calc R . . H3B H 1.2480 -0.0318 0.2316 0.052 Uiso 1 1 calc R . . N1 N 0.85189(17) -0.05205(17) 0.24327(5) 0.0504(4) Uani 1 1 d . . . H1A H 0.8549 -0.1207 0.2643 0.060 Uiso 1 1 calc R . . H1B H 0.7512 -0.0142 0.2331 0.060 Uiso 1 1 calc R . . N2 N 0.99360(17) 0.09639(16) 0.19484(5) 0.0464(3) Uani 1 1 d . . . H2A H 1.0909 0.1264 0.1837 0.056 Uiso 1 1 calc R . . H2B H 0.8927 0.1341 0.1847 0.056 Uiso 1 1 calc R . . O2 O 0.33111(12) 0.22857(11) 0.18158(3) 0.0373(2) Uani 1 1 d . . . O3 O 0.64718(12) 0.22041(12) 0.18885(3) 0.0389(2) Uani 1 1 d . . . O1 O 0.48215(13) 0.00488(12) 0.20269(3) 0.0407(2) Uani 1 1 d . . . O4 O 0.81438(16) 0.63712(13) 0.03880(4) 0.0539(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 0.02702(17) 0.03854(19) 0.02725(17) -0.00209(12) 0.00323(12) 0.00127(12) C5 0.0280(6) 0.0304(6) 0.0282(6) 0.0005(5) 0.0030(5) 0.0003(5) C2 0.0272(6) 0.0330(6) 0.0268(6) -0.0013(5) 0.0033(5) -0.0007(5) C6 0.0602(10) 0.0342(7) 0.0305(7) 0.0023(6) -0.0017(6) 0.0148(7) C7 0.0569(9) 0.0336(7) 0.0337(7) -0.0027(6) 0.0016(6) 0.0159(7) C1 0.0328(7) 0.0475(8) 0.0320(7) 0.0056(6) 0.0039(5) 0.0017(6) C4 0.0482(8) 0.0450(8) 0.0324(7) -0.0024(6) 0.0011(6) 0.0220(7) C3 0.0501(9) 0.0472(9) 0.0298(7) 0.0023(6) -0.0016(6) 0.0204(7) C8 0.0373(8) 0.0469(9) 0.0628(10) 0.0065(8) 0.0007(7) -0.0009(7) C12 0.0504(9) 0.0473(9) 0.0607(10) 0.0196(8) 0.0108(8) 0.0078(7) C15 0.0584(12) 0.0702(14) 0.129(2) 0.0411(14) 0.0355(13) 0.0087(10) C10 0.106(2) 0.103(2) 0.0591(13) 0.0019(13) -0.0318(13) 0.0045(16) C14 0.0502(11) 0.0765(14) 0.0867(15) 0.0040(12) 0.0193(10) 0.0062(10) C16 0.0753(13) 0.0428(10) 0.0819(14) 0.0199(9) 0.0102(11) 0.0103(9) C13 0.0582(12) 0.0563(12) 0.1161(19) 0.0296(12) 0.0091(12) -0.0077(9) C11 0.109(2) 0.0868(17) 0.0514(11) 0.0152(11) 0.0140(12) 0.0144(15) C9 0.0674(13) 0.0743(14) 0.0816(15) -0.0133(12) -0.0189(11) -0.0058(11) N4 0.0371(6) 0.0375(7) 0.0489(7) 0.0097(5) -0.0012(5) 0.0043(5) N3 0.0324(6) 0.0569(8) 0.0416(7) 0.0175(6) 0.0027(5) 0.0012(6) N1 0.0326(6) 0.0674(9) 0.0516(8) 0.0269(7) 0.0071(6) 0.0048(6) N2 0.0321(6) 0.0600(8) 0.0476(7) 0.0216(6) 0.0064(5) 0.0038(6) O2 0.0299(5) 0.0472(6) 0.0352(5) -0.0066(4) 0.0046(4) 0.0040(4) O3 0.0294(5) 0.0492(6) 0.0380(5) -0.0098(4) 0.0019(4) -0.0013(4) O1 0.0425(6) 0.0477(6) 0.0326(5) 0.0067(4) 0.0068(4) 0.0023(5) O4 0.0517(7) 0.0492(7) 0.0581(7) 0.0123(5) -0.0150(5) 0.0031(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4545(11) . ? S1 O2 1.4592(10) . ? S1 O3 1.4639(10) . ? S1 C2 1.7646(13) . ? C5 C6 1.3891(19) . ? C5 C4 1.3927(19) . ? C5 C5 1.493(2) 3_655 ? C2 C7 1.3767(19) . ? C2 C3 1.377(2) . ? C6 C7 1.388(2) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? C1 N3 1.3229(19) . ? C1 N1 1.3249(19) . ? C1 N2 1.3265(19) . ? C4 C3 1.389(2) . ? C4 H4 0.9500 . ? C3 H3 0.9500 . ? C8 N4 1.489(2) . ? C8 C9 1.521(3) . ? C8 C13 1.522(3) . ? C8 C14 1.534(3) . ? C12 N4 1.496(2) . ? C12 C15 1.525(3) . ? C12 C11 1.530(3) . ? C12 C16 1.532(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C10 C9 1.507(4) . ? C10 C11 1.507(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? N4 O4 1.2814(17) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 113.06(6) . . ? O1 S1 O3 111.53(6) . . ? O2 S1 O3 111.73(6) . . ? O1 S1 C2 106.91(6) . . ? O2 S1 C2 106.80(6) . . ? O3 S1 C2 106.35(6) . . ? C6 C5 C4 117.97(12) . . ? C6 C5 C5 121.50(15) . 3_655 ? C4 C5 C5 120.53(15) . 3_655 ? C7 C2 C3 120.08(12) . . ? C7 C2 S1 120.55(10) . . ? C3 C2 S1 119.35(10) . . ? C7 C6 C5 121.06(13) . . ? C7 C6 H6 119.5 . . ? C5 C6 H6 119.5 . . ? C2 C7 C6 119.97(13) . . ? C2 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? N3 C1 N1 119.95(13) . . ? N3 C1 N2 120.20(13) . . ? N1 C1 N2 119.83(13) . . ? C3 C4 C5 121.05(13) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C2 C3 C4 119.86(13) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? N4 C8 C9 109.15(16) . . ? N4 C8 C13 107.64(14) . . ? C9 C8 C13 109.87(18) . . ? N4 C8 C14 108.83(15) . . ? C9 C8 C14 111.77(17) . . ? C13 C8 C14 109.48(17) . . ? N4 C12 C15 107.53(14) . . ? N4 C12 C11 109.51(16) . . ? C15 C12 C11 109.65(19) . . ? N4 C12 C16 109.26(15) . . ? C15 C12 C16 109.03(18) . . ? C11 C12 C16 111.77(17) . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C9 C10 C11 109.1(2) . . ? C9 C10 H10A 109.9 . . ? C11 C10 H10A 109.9 . . ? C9 C10 H10B 109.9 . . ? C11 C10 H10B 109.9 . . ? H10A C10 H10B 108.3 . . ? C8 C14 H14A 109.5 . . ? C8 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C8 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 C13 H13A 109.5 . . ? C8 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C8 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C11 C12 113.44(18) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C10 C9 C8 113.76(18) . . ? C10 C9 H9A 108.8 . . ? C8 C9 H9A 108.8 . . ? C10 C9 H9B 108.8 . . ? C8 C9 H9B 108.8 . . ? H9A C9 H9B 107.7 . . ? O4 N4 C8 116.45(13) . . ? O4 N4 C12 115.33(13) . . ? C8 N4 C12 124.43(13) . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 S1 C2 C7 147.44(12) . . . . ? O2 S1 C2 C7 26.15(14) . . . . ? O3 S1 C2 C7 -93.29(13) . . . . ? O1 S1 C2 C3 -33.94(13) . . . . ? O2 S1 C2 C3 -155.23(12) . . . . ? O3 S1 C2 C3 85.33(13) . . . . ? C4 C5 C6 C7 -0.7(2) . . . . ? C5 C5 C6 C7 178.27(16) 3_655 . . . ? C3 C2 C7 C6 0.3(2) . . . . ? S1 C2 C7 C6 178.86(12) . . . . ? C5 C6 C7 C2 0.5(3) . . . . ? C6 C5 C4 C3 0.1(2) . . . . ? C5 C5 C4 C3 -178.84(16) 3_655 . . . ? C7 C2 C3 C4 -0.8(2) . . . . ? S1 C2 C3 C4 -179.43(13) . . . . ? C5 C4 C3 C2 0.6(3) . . . . ? C9 C10 C11 C12 59.6(3) . . . . ? N4 C12 C11 C10 -45.7(3) . . . . ? C15 C12 C11 C10 -163.4(2) . . . . ? C16 C12 C11 C10 75.6(2) . . . . ? C11 C10 C9 C8 -60.6(3) . . . . ? N4 C8 C9 C10 47.1(3) . . . . ? C13 C8 C9 C10 164.9(2) . . . . ? C14 C8 C9 C10 -73.4(3) . . . . ? C9 C8 N4 O4 166.37(15) . . . . ? C13 C8 N4 O4 47.2(2) . . . . ? C14 C8 N4 O4 -71.40(18) . . . . ? C9 C8 N4 C12 -36.6(2) . . . . ? C13 C8 N4 C12 -155.85(18) . . . . ? C14 C8 N4 C12 85.6(2) . . . . ? C15 C12 N4 O4 -47.6(2) . . . . ? C11 C12 N4 O4 -166.68(16) . . . . ? C16 C12 N4 O4 70.60(19) . . . . ? C15 C12 N4 C8 155.18(18) . . . . ? C11 C12 N4 C8 36.1(2) . . . . ? C16 C12 N4 C8 -86.6(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 N3 H3A O2 0.88 2.05 2.9291(16) 172.8 2_645 N3 H3B O1 0.88 2.06 2.9355(16) 170.3 1_655 N1 H1A O3 0.88 2.00 2.8836(17) 177.8 2_645 N1 H1B O1 0.88 2.19 3.0376(17) 161.1 . N2 H2A O2 0.88 2.08 2.9139(16) 158.9 1_655 N2 H2B O3 0.88 2.06 2.8885(16) 157.0 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.312 _refine_diff_density_min -0.342 _refine_diff_density_rms 0.038 # Attachment '- GDS 3.cif' data_GDS_3 _database_code_depnum_ccdc_archive 'CCDC 802081' #TrackingRef '- GDS 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19.50 H33 N8.50 O7.50 S2' _chemical_formula_weight 570.66 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.4293(17) _cell_length_b 12.136(3) _cell_length_c 16.373(4) _cell_angle_alpha 71.479(4) _cell_angle_beta 88.241(4) _cell_angle_gamma 87.373(4) _cell_volume 1398.1(6) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9737 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 28.68 _exptl_crystal_description slab _exptl_crystal_colour orange _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.356 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 603 _exptl_absorpt_coefficient_mu 0.246 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8766 _exptl_absorpt_correction_T_max 0.9687 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13424 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 30.65 _reflns_number_total 13424 _reflns_number_gt 12401 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0661P)^2^+0.4946P] 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 13424 _refine_ls_number_parameters 416 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0509 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1321 _refine_ls_wR_factor_gt 0.1283 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 0.52770(4) 0.12418(3) 0.34271(2) 0.02582(8) Uani 1 1 d . A 5 S2 S 0.99112(4) 0.34634(3) 0.62231(2) 0.02814(8) Uani 1 1 d . B 5 C1 C 0.50625(19) 0.24219(12) 0.54245(9) 0.0279(3) Uani 1 1 d . C 5 C3 C 0.51385(18) 0.10345(11) 0.24084(9) 0.0267(3) Uani 1 1 d . A 5 C9 C 0.9900(2) 0.23919(13) 0.72541(10) 0.0325(3) Uani 1 1 d . B 5 C2 C 0.9833(2) 0.69583(12) 0.64310(9) 0.0321(3) Uani 1 1 d . D 5 C6 C 0.5070(2) 0.06347(13) 0.08389(9) 0.0345(3) Uani 1 1 d . A 5 C4 C 0.5679(2) 0.18902(12) 0.16701(10) 0.0339(3) Uani 1 1 d . A 5 H4 H 0.6077 0.2607 0.1703 0.041 Uiso 1 1 calc R A 5 C8 C 0.4527(2) -0.00158(14) 0.23666(10) 0.0396(4) Uani 1 1 d . A 5 H8 H 0.4129 -0.0591 0.2875 0.048 Uiso 1 1 calc R A 5 C12 C 1.0062(3) 0.07654(16) 0.88761(12) 0.0473(4) Uani 1 1 d . B 5 C5 C 0.5634(2) 0.16931(13) 0.08792(10) 0.0382(3) Uani 1 1 d . A 5 H5 H 0.5987 0.2280 0.0368 0.046 Uiso 1 1 calc R A 5 C7 C 0.4502(3) -0.02156(14) 0.15798(11) 0.0427(4) Uani 1 1 d . A 5 H7 H 0.4098 -0.0932 0.1547 0.051 Uiso 1 1 calc R A 5 C10 C 1.0521(3) 0.12588(15) 0.73517(12) 0.0468(4) Uani 1 1 d . B 5 H10 H 1.0900 0.1042 0.6863 0.056 Uiso 1 1 calc R B 5 C14 C 0.9312(3) 0.27073(16) 0.79638(12) 0.0505(4) Uani 1 1 d . B 5 H14 H 0.8850 0.3474 0.7894 0.061 Uiso 1 1 calc R B 5 C11 C 1.0582(3) 0.04497(17) 0.81696(13) 0.0544(5) Uani 1 1 d . B 5 H11 H 1.0987 -0.0328 0.8240 0.065 Uiso 1 1 calc R B 5 C13 C 0.9406(3) 0.18865(19) 0.87789(12) 0.0557(5) Uani 1 1 d . B 5 H13 H 0.9021 0.2095 0.9271 0.067 Uiso 1 1 calc R B 5 N4 N 1.14166(17) 0.64006(11) 0.64465(9) 0.0351(3) Uani 1 1 d . D 5 H4A H 1.2416 0.6753 0.6465 0.042 Uiso 1 1 calc R D 5 H4B H 1.1467 0.5678 0.6438 0.042 Uiso 1 1 calc R D 5 N6 N 0.83202(17) 0.64265(11) 0.64188(9) 0.0346(3) Uani 1 1 d . D 5 H6A H 0.7273 0.6795 0.6419 0.042 Uiso 1 1 calc R D 5 H6B H 0.8363 0.5704 0.6410 0.042 Uiso 1 1 calc R D 5 N7 N 0.5108(2) 0.05088(12) -0.00030(8) 0.0389(3) Uani 1 1 d . . 5 N3 N 0.35488(16) 0.18949(10) 0.54181(8) 0.0321(3) Uani 1 1 d . C 5 H3A H 0.3585 0.1174 0.5407 0.038 Uiso 1 1 calc R C 5 H3B H 0.2504 0.2265 0.5425 0.038 Uiso 1 1 calc R C 5 N1 N 0.66360(16) 0.18636(11) 0.54145(9) 0.0326(3) Uani 1 1 d . C 5 H1A H 0.6671 0.1143 0.5404 0.039 Uiso 1 1 calc R C 5 H1B H 0.7645 0.2214 0.5419 0.039 Uiso 1 1 calc R C 5 N2 N 0.50045(18) 0.35161(11) 0.54328(11) 0.0419(3) Uani 1 1 d . C 5 H2A H 0.3959 0.3887 0.5434 0.050 Uiso 1 1 calc R C 5 H2B H 0.6012 0.3869 0.5437 0.050 Uiso 1 1 calc R C 5 N5 N 0.97601(19) 0.80451(12) 0.64437(12) 0.0468(4) Uani 1 1 d . D 5 H5A H 0.8710 0.8411 0.6444 0.056 Uiso 1 1 calc R D 5 H5B H 1.0762 0.8401 0.6452 0.056 Uiso 1 1 calc R D 5 N8 N 1.0199(2) -0.01702(15) 0.96930(11) 0.0521(4) Uani 1 1 d . . 5 O3 O 0.37229(14) 0.06835(9) 0.39314(7) 0.0336(2) Uani 1 1 d . A 5 O2 O 0.52338(14) 0.24957(8) 0.32678(7) 0.0319(2) Uani 1 1 d . A 5 O4 O 0.99923(14) 0.28335(9) 0.55984(7) 0.0331(2) Uani 1 1 d . B 5 O1 O 0.69718(14) 0.06698(9) 0.37958(7) 0.0350(2) Uani 1 1 d . A 5 O5 O 1.15124(14) 0.41296(9) 0.61836(8) 0.0362(2) Uani 1 1 d . B 5 O6 O 0.82425(14) 0.41602(9) 0.61777(8) 0.0361(2) Uani 1 1 d . B 5 O1M O 0.5191(6) 0.5978(5) 0.1056(4) 0.107(2) Uani 0.437(6) 1 d P E 1 H1M H 0.5817 0.5525 0.0857 0.160 Uiso 0.437(6) 1 calc PR E 1 C1M C 0.561(4) 0.5639(17) 0.2182(19) 0.329(18) Uani 0.437(6) 1 d P E 1 H1M1 H 0.6797 0.5914 0.2258 0.494 Uiso 0.437(6) 1 calc PR E 1 H1M2 H 0.5593 0.4795 0.2460 0.494 Uiso 0.437(6) 1 calc PR E 1 H1M3 H 0.4681 0.6022 0.2445 0.494 Uiso 0.437(6) 1 calc PR E 1 O1M' O 0.5654(10) 0.6507(9) 0.2051(6) 0.196(4) Uani 0.563(6) 1 d P E 2 H1M' H 0.6778 0.6534 0.1978 0.294 Uiso 0.563(6) 1 calc PR E 2 C1M' C 0.4873(7) 0.6968(4) 0.1315(3) 0.0685(13) Uani 0.563(6) 1 d P E 2 H1M4 H 0.3795 0.7424 0.1393 0.103 Uiso 0.563(6) 1 calc PR E 2 H1M5 H 0.4526 0.6351 0.1091 0.103 Uiso 0.563(6) 1 calc PR E 2 H1M6 H 0.5708 0.7478 0.0907 0.103 Uiso 0.563(6) 1 calc PR E 2 O1T O 1.2349(8) 0.5290(4) -0.0735(4) 0.0664(13) Uani 0.50 1 d P F -1 N1T N 1.0904(4) 0.5461(3) -0.0207(2) 0.0442(6) Uani 0.50 1 d P F -1 C1T C 1.0803(7) 0.3990(4) 0.0639(3) 0.0456(10) Uani 0.50 1 d P F -1 C2T C 0.9399(6) 0.4551(4) 0.1199(2) 0.0528(9) Uani 0.50 1 d P F -1 H2T1 H 0.9564 0.5388 0.1106 0.063 Uiso 0.50 1 calc PR F -1 H2T2 H 0.9370 0.4108 0.1822 0.063 Uiso 0.50 1 calc PR F -1 C3T C 0.7627(13) 0.4288(6) 0.0644(6) 0.0600(17) Uani 0.50 1 d P F -1 H3T1 H 0.6519 0.4045 0.0994 0.072 Uiso 0.50 1 calc PR F -1 H3T2 H 0.7938 0.3784 0.0285 0.072 Uiso 0.50 1 calc PR F -1 C4T C 0.7715(6) 0.5979(4) 0.0026(3) 0.0584(10) Uani 0.50 1 d P F -1 H4T1 H 0.6557 0.6356 -0.0222 0.070 Uiso 0.50 1 calc PR F -1 H4T2 H 0.8316 0.6433 0.0338 0.070 Uiso 0.50 1 calc PR F -1 C5T C 0.9009(7) 0.5528(4) -0.0622(3) 0.0444(10) Uani 0.50 1 d P F -1 C6T C 0.8753(8) 0.5343(5) -0.1262(3) 0.0717(14) Uani 0.50 1 d P F -1 H6T1 H 0.9908 0.5271 -0.1550 0.108 Uiso 0.50 1 calc PR F -1 H6T2 H 0.8019 0.5985 -0.1638 0.108 Uiso 0.50 1 calc PR F -1 H6T3 H 0.8116 0.4617 -0.1137 0.108 Uiso 0.50 1 calc PR F -1 C7T C 0.9569(6) 0.7278(4) -0.1161(3) 0.0628(12) Uani 0.50 1 d P F -1 H7T1 H 1.0453 0.7371 -0.1633 0.094 Uiso 0.50 1 calc PR F -1 H7T2 H 1.0061 0.7563 -0.0720 0.094 Uiso 0.50 1 calc PR F -1 H7T3 H 0.8458 0.7725 -0.1384 0.094 Uiso 0.50 1 calc PR F -1 C8T C 1.0997(7) 0.3321(4) 0.0419(3) 0.0640(11) Uani 0.50 1 d P F -1 H8T1 H 1.1268 0.2615 0.0901 0.096 Uiso 0.50 1 calc PR F -1 H8T2 H 1.2010 0.3467 0.0005 0.096 Uiso 0.50 1 calc PR F -1 H8T3 H 0.9906 0.3217 0.0134 0.096 Uiso 0.50 1 calc PR F -1 C9T C 1.2743(7) 0.4544(4) 0.1051(3) 0.0659(12) Uani 0.50 1 d P F -1 H9T1 H 1.2951 0.4074 0.1652 0.099 Uiso 0.50 1 calc PR F -1 H9T2 H 1.2485 0.5356 0.1019 0.099 Uiso 0.50 1 calc PR F -1 H9T3 H 1.3820 0.4496 0.0702 0.099 Uiso 0.50 1 calc PR F -1 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 0.03312(16) 0.02450(15) 0.02228(15) -0.01065(12) -0.00147(12) -0.00203(11) S2 0.02928(15) 0.02812(15) 0.02721(16) -0.00888(13) -0.00212(13) -0.00130(11) C1 0.0347(7) 0.0272(6) 0.0218(6) -0.0078(5) -0.0003(5) -0.0024(5) C3 0.0318(6) 0.0284(6) 0.0225(6) -0.0115(5) -0.0020(5) -0.0014(5) C9 0.0344(7) 0.0350(7) 0.0269(7) -0.0076(6) -0.0016(5) -0.0042(5) C2 0.0370(7) 0.0312(6) 0.0271(7) -0.0073(5) -0.0023(5) -0.0024(5) C6 0.0445(8) 0.0392(8) 0.0228(7) -0.0138(6) -0.0029(6) -0.0024(6) C4 0.0466(8) 0.0280(6) 0.0285(7) -0.0105(5) 0.0009(6) -0.0051(6) C8 0.0610(10) 0.0343(7) 0.0263(7) -0.0116(6) 0.0027(7) -0.0177(7) C12 0.0489(9) 0.0499(10) 0.0356(9) -0.0020(7) -0.0054(7) -0.0053(7) C5 0.0564(9) 0.0341(7) 0.0240(7) -0.0088(6) 0.0032(6) -0.0056(6) C7 0.0669(11) 0.0391(8) 0.0281(7) -0.0171(6) 0.0019(7) -0.0184(7) C10 0.0590(11) 0.0413(9) 0.0339(9) -0.0054(7) 0.0057(7) 0.0105(8) C14 0.0792(13) 0.0399(9) 0.0353(9) -0.0163(7) 0.0015(8) -0.0029(8) C11 0.0685(12) 0.0438(9) 0.0409(10) -0.0017(8) 0.0029(9) 0.0125(8) C13 0.0815(14) 0.0583(11) 0.0306(9) -0.0183(8) 0.0028(9) -0.0081(10) N4 0.0336(6) 0.0317(6) 0.0407(7) -0.0118(5) -0.0043(5) -0.0027(5) N6 0.0332(6) 0.0311(6) 0.0400(7) -0.0116(5) -0.0017(5) -0.0022(5) N7 0.0531(8) 0.0436(7) 0.0241(6) -0.0162(5) -0.0030(5) -0.0026(6) N3 0.0328(6) 0.0292(6) 0.0373(7) -0.0146(5) -0.0018(5) -0.0019(4) N1 0.0318(6) 0.0294(6) 0.0388(7) -0.0140(5) -0.0010(5) -0.0014(4) N2 0.0346(6) 0.0297(6) 0.0653(10) -0.0201(6) -0.0019(6) -0.0019(5) N5 0.0372(7) 0.0347(7) 0.0716(11) -0.0208(7) -0.0051(7) -0.0018(5) N8 0.0606(10) 0.0541(9) 0.0410(8) -0.0142(7) 0.0008(7) -0.0013(7) O3 0.0413(5) 0.0320(5) 0.0298(5) -0.0133(4) 0.0073(4) -0.0062(4) O2 0.0406(5) 0.0258(4) 0.0326(5) -0.0137(4) -0.0013(4) -0.0021(4) O4 0.0349(5) 0.0383(5) 0.0290(5) -0.0147(4) -0.0012(4) -0.0014(4) O1 0.0392(5) 0.0317(5) 0.0346(6) -0.0106(4) -0.0115(4) 0.0009(4) O5 0.0343(5) 0.0340(5) 0.0415(6) -0.0131(5) 0.0000(4) -0.0057(4) O6 0.0328(5) 0.0348(5) 0.0416(6) -0.0138(5) -0.0034(4) 0.0033(4) O1M 0.069(3) 0.097(4) 0.130(5) -0.006(3) 0.000(3) 0.013(2) C1M 0.47(4) 0.127(14) 0.37(4) -0.03(2) -0.13(3) 0.01(2) O1M' 0.121(4) 0.197(8) 0.190(7) 0.057(6) -0.063(4) -0.013(5) C1M' 0.081(3) 0.068(3) 0.058(3) -0.022(2) 0.000(2) -0.001(2) O1T 0.053(2) 0.087(4) 0.048(2) -0.005(3) 0.0079(15) -0.019(3) N1T 0.0501(16) 0.0409(14) 0.0392(16) -0.0079(12) -0.0003(13) -0.0111(12) C1T 0.056(2) 0.037(2) 0.042(2) -0.008(2) -0.0115(16) -0.006(2) C2T 0.071(3) 0.054(2) 0.0304(17) -0.0089(15) 0.0032(17) -0.0130(18) C3T 0.063(3) 0.045(3) 0.065(4) -0.010(2) 0.020(3) -0.012(3) C4T 0.050(2) 0.057(2) 0.062(3) -0.008(2) -0.0024(19) -0.0040(17) C5T 0.057(2) 0.038(2) 0.039(2) -0.010(2) -0.0087(16) -0.004(2) C6T 0.086(4) 0.078(3) 0.050(3) -0.014(2) -0.019(2) -0.025(3) C7T 0.068(3) 0.049(2) 0.053(2) 0.0111(18) -0.005(2) -0.0081(18) C8T 0.080(3) 0.043(2) 0.064(3) -0.011(2) 0.000(2) -0.004(2) C9T 0.066(3) 0.067(3) 0.061(3) -0.013(2) -0.022(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4589(10) . ? S1 O3 1.4601(11) . ? S1 O1 1.4601(11) . ? S1 C3 1.7708(14) . ? S2 O4 1.4569(11) . ? S2 O5 1.4571(11) . ? S2 O6 1.4585(11) . ? S2 C9 1.7737(16) . ? C1 N3 1.3209(18) . ? C1 N1 1.3263(18) . ? C1 N2 1.3310(18) . ? C3 C4 1.383(2) . ? C3 C8 1.3951(19) . ? C9 C14 1.387(2) . ? C9 C10 1.392(2) . ? C2 N5 1.3243(19) . ? C2 N6 1.3251(19) . ? C2 N4 1.3271(19) . ? C6 C7 1.388(2) . ? C6 C5 1.391(2) . ? C6 N7 1.4335(18) . ? C4 C5 1.391(2) . ? C4 H4 0.9500 . ? C8 C7 1.385(2) . ? C8 H8 0.9500 . ? C12 C11 1.369(3) . ? C12 C13 1.386(3) . ? C12 N8 1.457(2) . ? C5 H5 0.9500 . ? C7 H7 0.9500 . ? C10 C11 1.387(3) . ? C10 H10 0.9500 . ? C14 C13 1.390(3) . ? C14 H14 0.9500 . ? C11 H11 0.9500 . ? C13 H13 0.9500 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N6 H6A 0.8800 . ? N6 H6B 0.8800 . ? N7 N7 1.250(3) 2_655 ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N8 N8 1.226(3) 2_757 ? O1M C1M 1.79(3) . ? O1M H1M 0.8400 . ? C1M H1M1 0.9800 . ? C1M H1M2 0.9800 . ? C1M H1M3 0.9800 . ? O1M' C1M' 1.299(8) . ? O1M' H1M' 0.8400 . ? C1M' H1M4 0.9800 . ? C1M' H1M5 0.9800 . ? C1M' H1M6 0.9800 . ? O1T N1T 1.407(6) . ? N1T C5T 1.569(6) . ? N1T C1T 1.882(6) . ? C1T C8T 0.991(6) . ? C1T C2T 1.633(7) . ? C1T C9T 1.850(7) . ? C2T C3T 1.720(10) . ? C2T H2T1 0.9900 . ? C2T H2T2 0.9900 . ? C3T C4T 1.982(8) . ? C3T H3T1 0.9900 . ? C3T H3T2 0.9900 . ? C4T C5T 1.614(7) . ? C4T H4T1 0.9900 . ? C4T H4T2 0.9900 . ? C5T C6T 1.162(7) . ? C5T C7T 2.081(6) . ? C6T H6T1 0.9800 . ? C6T H6T2 0.9800 . ? C6T H6T3 0.9800 . ? C7T H7T1 0.9800 . ? C7T H7T2 0.9800 . ? C7T H7T3 0.9800 . ? C8T H8T1 0.9800 . ? C8T H8T2 0.9800 . ? C8T H8T3 0.9800 . ? C9T H9T1 0.9800 . ? C9T H9T2 0.9800 . ? C9T H9T3 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 O2 S1 O3 112.80(6) . . ? O2 S1 O1 112.84(6) . . ? O3 S1 O1 111.72(7) . . ? O2 S1 C3 106.51(6) . . ? O3 S1 C3 106.21(6) . . ? O1 S1 C3 106.16(6) . . ? O4 S2 O5 112.26(7) . . ? O4 S2 O6 112.61(6) . . ? O5 S2 O6 112.78(6) . . ? O4 S2 C9 106.19(7) . . ? O5 S2 C9 106.18(7) . . ? O6 S2 C9 106.18(7) . . ? N3 C1 N1 119.95(12) . . ? N3 C1 N2 119.88(13) . . ? N1 C1 N2 120.17(13) . . ? C4 C3 C8 120.72(13) . . ? C4 C3 S1 120.27(10) . . ? C8 C3 S1 118.99(11) . . ? C14 C9 C10 120.53(15) . . ? C14 C9 S2 119.09(13) . . ? C10 C9 S2 120.35(12) . . ? N5 C2 N6 119.74(14) . . ? N5 C2 N4 119.91(14) . . ? N6 C2 N4 120.34(13) . . ? C7 C6 C5 120.45(14) . . ? C7 C6 N7 124.01(13) . . ? C5 C6 N7 115.54(13) . . ? C3 C4 C5 119.52(13) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? C7 C8 C3 119.67(14) . . ? C7 C8 H8 120.2 . . ? C3 C8 H8 120.2 . . ? C11 C12 C13 120.32(16) . . ? C11 C12 N8 114.54(17) . . ? C13 C12 N8 125.10(18) . . ? C6 C5 C4 119.86(14) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C8 C7 C6 119.75(14) . . ? C8 C7 H7 120.1 . . ? C6 C7 H7 120.1 . . ? C11 C10 C9 119.34(17) . . ? C11 C10 H10 120.3 . . ? C9 C10 H10 120.3 . . ? C9 C14 C13 119.15(17) . . ? C9 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C12 C11 C10 120.42(18) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C12 C13 C14 120.18(18) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C2 N4 H4A 120.0 . . ? C2 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C2 N6 H6A 120.0 . . ? C2 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? N7 N7 C6 113.60(16) 2_655 . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C2 N5 H5A 120.0 . . ? C2 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? N8 N8 C12 111.9(2) 2_757 . ? C1M' O1M' H1M' 109.5 . . ? O1M' C1M' H1M4 109.5 . . ? O1M' C1M' H1M5 109.5 . . ? H1M4 C1M' H1M5 109.5 . . ? O1M' C1M' H1M6 109.5 . . ? H1M4 C1M' H1M6 109.5 . . ? H1M5 C1M' H1M6 109.5 . . ? O1T N1T C5T 113.7(4) . . ? O1T N1T C1T 101.9(3) . . ? C5T N1T C1T 99.8(2) . . ? C8T C1T C2T 142.8(5) . . ? C8T C1T C9T 119.2(5) . . ? C2T C1T C9T 91.0(3) . . ? C8T C1T N1T 114.9(5) . . ? C2T C1T N1T 89.1(3) . . ? C9T C1T N1T 81.4(3) . . ? C1T C2T C3T 89.9(4) . . ? C1T C2T H2T1 113.7 . . ? C3T C2T H2T1 113.7 . . ? C1T C2T H2T2 113.7 . . ? C3T C2T H2T2 113.7 . . ? H2T1 C2T H2T2 110.9 . . ? C2T C3T C4T 83.3(3) . . ? C2T C3T H3T1 114.7 . . ? C4T C3T H3T1 114.7 . . ? C2T C3T H3T2 114.7 . . ? C4T C3T H3T2 114.7 . . ? H3T1 C3T H3T2 111.8 . . ? C5T C4T C3T 82.0(4) . . ? C5T C4T H4T1 115.0 . . ? C3T C4T H4T1 115.0 . . ? C5T C4T H4T2 115.0 . . ? C3T C4T H4T2 115.0 . . ? H4T1 C4T H4T2 112.0 . . ? C6T C5T N1T 125.0(5) . . ? C6T C5T C4T 132.9(5) . . ? N1T C5T C4T 101.9(3) . . ? C6T C5T C7T 97.3(4) . . ? N1T C5T C7T 83.0(3) . . ? C4T C5T C7T 84.1(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 O2 S1 C3 C4 24.03(14) . . . . ? O3 S1 C3 C4 144.49(12) . . . . ? O1 S1 C3 C4 -96.46(13) . . . . ? O2 S1 C3 C8 -157.80(13) . . . . ? O3 S1 C3 C8 -37.33(14) . . . . ? O1 S1 C3 C8 81.71(14) . . . . ? O4 S2 C9 C14 -161.46(14) . . . . ? O5 S2 C9 C14 78.88(15) . . . . ? O6 S2 C9 C14 -41.38(16) . . . . ? O4 S2 C9 C10 20.39(15) . . . . ? O5 S2 C9 C10 -99.28(14) . . . . ? O6 S2 C9 C10 140.46(14) . . . . ? C8 C3 C4 C5 -0.9(2) . . . . ? S1 C3 C4 C5 177.25(12) . . . . ? C4 C3 C8 C7 1.6(3) . . . . ? S1 C3 C8 C7 -176.56(14) . . . . ? C7 C6 C5 C4 1.8(3) . . . . ? N7 C6 C5 C4 -178.74(15) . . . . ? C3 C4 C5 C6 -0.8(2) . . . . ? C3 C8 C7 C6 -0.6(3) . . . . ? C5 C6 C7 C8 -1.1(3) . . . . ? N7 C6 C7 C8 179.51(16) . . . . ? C14 C9 C10 C11 -1.3(3) . . . . ? S2 C9 C10 C11 176.86(16) . . . . ? C10 C9 C14 C13 2.1(3) . . . . ? S2 C9 C14 C13 -176.05(16) . . . . ? C13 C12 C11 C10 2.3(3) . . . . ? N8 C12 C11 C10 -179.87(19) . . . . ? C9 C10 C11 C12 -1.0(3) . . . . ? C11 C12 C13 C14 -1.5(3) . . . . ? N8 C12 C13 C14 -179.0(2) . . . . ? C9 C14 C13 C12 -0.7(3) . . . . ? C7 C6 N7 N7 -12.1(3) . . . 2_655 ? C5 C6 N7 N7 168.48(19) . . . 2_655 ? C11 C12 N8 N8 176.7(2) . . . 2_757 ? C13 C12 N8 N8 -5.6(3) . . . 2_757 ? O1T N1T C1T C8T -40.2(6) . . . . ? C5T N1T C1T C8T 76.8(6) . . . . ? O1T N1T C1T C2T 169.2(3) . . . . ? C5T N1T C1T C2T -73.8(3) . . . . ? O1T N1T C1T C9T 78.1(4) . . . . ? C5T N1T C1T C9T -164.9(3) . . . . ? C8T C1T C2T C3T -45.4(9) . . . . ? C9T C1T C2T C3T 168.5(4) . . . . ? N1T C1T C2T C3T 87.1(3) . . . . ? C1T C2T C3T C4T -102.9(3) . . . . ? C2T C3T C4T C5T 92.7(4) . . . . ? O1T N1T C5T C6T 7.4(7) . . . . ? C1T N1T C5T C6T -100.3(6) . . . . ? O1T N1T C5T C4T -168.9(3) . . . . ? C1T N1T C5T C4T 83.3(3) . . . . ? O1T N1T C5T C7T -86.5(4) . . . . ? C1T N1T C5T C7T 165.7(3) . . . . ? C3T C4T C5T C6T 96.2(7) . . . . ? C3T C4T C5T N1T -87.8(4) . . . . ? C3T C4T C5T C7T -169.3(4) . . . . ? _diffrn_measured_fraction_theta_max 0.911 _diffrn_reflns_theta_full 30.65 _diffrn_measured_fraction_theta_full 0.911 _refine_diff_density_max 0.616 _refine_diff_density_min -0.311 _refine_diff_density_rms 0.059 # Attachment '- GDS 4.cif' data_GDS_4 _database_code_depnum_ccdc_archive 'CCDC 802082' #TrackingRef '- GDS 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H48 N13 O14 S4' _chemical_formula_weight 1039.13 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 7.3764(6) _cell_length_b 12.1391(10) _cell_length_c 16.7417(17) _cell_angle_alpha 71.3920(10) _cell_angle_beta 85.142(2) _cell_angle_gamma 86.8870(10) _cell_volume 1415.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 4780 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 26.06 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 543 _exptl_absorpt_coefficient_mu 0.234 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8803 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 5816 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.29 _diffrn_reflns_theta_max 26.45 _reflns_number_total 5816 _reflns_number_gt 4852 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5816 _refine_ls_number_parameters 354 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.1394 _refine_ls_R_factor_gt 0.1209 _refine_ls_wR_factor_ref 0.4020 _refine_ls_wR_factor_gt 0.3826 _refine_ls_goodness_of_fit_ref 1.783 _refine_ls_restrained_S_all 1.785 _refine_ls_shift/su_max 0.050 _refine_ls_shift/su_mean 0.005 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 0.9940(2) 0.75828(13) 0.96002(10) 0.0351(4) Uani 1 1 d . . . N1 N 0.9982(2) 0.64697(12) 0.96023(11) 0.0506(5) Uani 1 1 d . . . H1A H 1.1031 0.6087 0.9603 0.061 Uiso 1 1 calc R . . H1B H 0.8962 0.6126 0.9603 0.061 Uiso 1 1 calc R . . N2 N 0.8359(2) 0.81446(12) 0.96031(9) 0.0407(4) Uani 1 1 d . . . H2A H 0.8317 0.8870 0.9604 0.049 Uiso 1 1 calc R . . H2B H 0.7345 0.7794 0.9604 0.049 Uiso 1 1 calc R . . N3 N 1.1458(2) 0.81011(12) 0.95993(9) 0.0401(4) Uani 1 1 d . . . H3A H 1.1423 0.8826 0.9601 0.048 Uiso 1 1 calc R . . H3B H 1.2510 0.7723 0.9597 0.048 Uiso 1 1 calc R . . C2 C 0.4632(3) 0.69776(15) 0.14317(11) 0.0401(5) Uani 1 1 d . . . N4 N 0.3098(2) 0.64317(12) 0.14242(9) 0.0413(4) Uani 1 1 d . . . H4A H 0.2034 0.6793 0.1435 0.050 Uiso 1 1 calc R . . H4B H 0.3158 0.5713 0.1409 0.050 Uiso 1 1 calc R . . N5 N 0.4520(2) 0.80371(13) 0.14547(12) 0.0555(5) Uani 1 1 d . . . H5A H 0.5514 0.8396 0.1473 0.067 Uiso 1 1 calc R . . H5B H 0.3452 0.8397 0.1451 0.067 Uiso 1 1 calc R . . N6 N 0.6226(2) 0.64188(12) 0.14361(9) 0.0404(4) Uani 1 1 d . . . H6A H 0.7231 0.6766 0.1455 0.049 Uiso 1 1 calc R . . H6B H 0.6281 0.5700 0.1420 0.049 Uiso 1 1 calc R . . C3 C -0.0345(2) 0.89604(14) 0.25518(10) 0.0373(4) Uani 1 1 d . . . C4 C -0.0772(3) 0.80864(18) 0.32834(13) 0.0568(6) Uani 1 1 d . . . H4 H -0.1147 0.7356 0.3271 0.068 Uiso 1 1 calc R . . C5 C -0.0645(4) 0.8296(2) 0.40477(13) 0.0671(7) Uani 1 1 d . . . H5 H -0.0914 0.7683 0.4557 0.080 Uiso 1 1 calc R . . C6 C -0.0160(3) 0.93201(19) 0.41021(11) 0.0516(6) Uani 1 1 d . . . C7 C 0.0268(3) 1.02099(18) 0.33507(12) 0.0615(6) Uani 1 1 d . . . H7 H 0.0616 1.0941 0.3373 0.074 Uiso 1 1 calc R . . C8 C 0.0193(3) 1.00414(17) 0.25730(12) 0.0592(6) Uani 1 1 d . . . H8 H 0.0500 1.0646 0.2064 0.071 Uiso 1 1 calc R . . C9 C -0.0066(3) 0.94931(19) 0.49411(11) 0.0594(6) Uani 1 1 d . . . H9 H -0.0104 0.8821 0.5427 0.071 Uiso 1 1 calc R . . S1 S -0.05121(6) 0.87717(3) 0.15557(2) 0.03369(10) Uani 1 1 d . . . O1 O 0.10780(17) 0.93324(10) 0.10192(7) 0.0396(3) Uani 1 1 d . . . O2 O -0.21994(17) 0.93425(10) 0.12360(8) 0.0453(4) Uani 1 1 d . . . O3 O -0.04852(17) 0.75244(9) 0.17042(7) 0.0408(3) Uani 1 1 d . . . C10 C 1.4841(3) 0.24444(16) 0.21938(12) 0.0452(5) Uani 1 1 d . . . C11 C 1.4435(6) 0.2785(2) 0.28926(15) 0.1001(13) Uani 1 1 d . . . H11 H 1.4077 0.3568 0.2836 0.120 Uiso 1 1 calc R . . C12 C 1.4554(6) 0.1952(3) 0.37013(17) 0.1135(14) Uani 1 1 d . . . H12 H 1.4332 0.2194 0.4188 0.136 Uiso 1 1 calc R . . C13 C 1.4979(3) 0.0818(2) 0.37994(14) 0.0584(7) Uani 1 1 d . . . C14 C 1.5270(4) 0.0480(2) 0.30798(15) 0.0719(9) Uani 1 1 d . . . H14 H 1.5484 -0.0319 0.3136 0.086 Uiso 1 1 calc R . . C15 C 1.5253(4) 0.12899(18) 0.22839(14) 0.0643(7) Uani 1 1 d . . . H15 H 1.5524 0.1052 0.1798 0.077 Uiso 1 1 calc R . . C16 C 1.5033(4) -0.0119(2) 0.46310(14) 0.0658(8) Uani 1 1 d . . . H16 H 1.5117 -0.0907 0.4642 0.079 Uiso 1 1 calc R . . S2 S 1.48284(6) 0.34974(3) 0.11875(3) 0.03774(11) Uani 1 1 d . . . O4 O 1.49479(17) 0.28603(11) 0.05773(7) 0.0429(3) Uani 1 1 d . . . O5 O 1.64122(18) 0.42072(11) 0.10998(8) 0.0457(4) Uani 1 1 d . . . O6 O 1.31073(18) 0.41593(11) 0.11785(9) 0.0494(4) Uani 1 1 d . . . O1M O 0.9347(9) 0.3710(4) 0.3751(3) 0.128(2) Uani 0.50 1 d P . . H1M H 1.0218 0.4056 0.3848 0.191 Uiso 0.50 1 calc PR . . C1M C 0.9361(11) 0.3913(12) 0.2783(5) 0.178(5) Uani 0.50 1 d P . . H1M1 H 0.8110 0.3922 0.2625 0.266 Uiso 0.50 1 calc PR . . H1M2 H 1.0070 0.3285 0.2643 0.266 Uiso 0.50 1 calc PR . . H1M3 H 0.9913 0.4660 0.2473 0.266 Uiso 0.50 1 calc PR . . O1T O 0.7176(6) 0.5456(4) 0.4269(3) 0.0907(15) Uani 0.50 1 d PD A -1 N1T N 0.5670(5) 0.5385(3) 0.4722(2) 0.0681(14) Uani 0.50 1 d PD A -1 C1T C 0.5846(5) 0.4297(4) 0.56471(18) 0.0518(11) Uani 0.50 1 d PD A -1 C2T C 0.4042(6) 0.4704(5) 0.6174(3) 0.085(2) Uani 0.50 1 d PD A -1 C3T C 0.2376(8) 0.4978(5) 0.5730(3) 0.088(2) Uani 0.50 1 d PD A -1 C4T C 0.2422(8) 0.6002(5) 0.5001(4) 0.095(2) Uani 0.50 1 d PD A -1 C5T C 0.4294(7) 0.6639(5) 0.4473(4) 0.092(2) Uani 0.50 1 d PD A -1 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 0.0465(8) 0.0324(7) 0.0283(6) -0.0119(5) -0.0018(6) -0.0055(6) N1 0.0503(8) 0.0334(6) 0.0708(9) -0.0209(6) -0.0009(8) -0.0020(6) N2 0.0457(7) 0.0360(6) 0.0448(7) -0.0188(5) -0.0017(6) -0.0037(6) N3 0.0445(7) 0.0365(6) 0.0436(7) -0.0187(5) -0.0024(6) -0.0023(6) C2 0.0485(9) 0.0394(8) 0.0335(7) -0.0120(6) -0.0030(6) -0.0072(7) N4 0.0420(7) 0.0380(7) 0.0451(7) -0.0147(6) -0.0021(6) -0.0038(6) N5 0.0449(8) 0.0440(7) 0.0853(10) -0.0303(7) -0.0070(8) -0.0027(6) N6 0.0433(7) 0.0355(6) 0.0445(7) -0.0140(5) -0.0068(6) -0.0044(6) C3 0.0473(9) 0.0387(7) 0.0307(6) -0.0171(5) -0.0017(6) -0.0065(7) C4 0.0828(13) 0.0477(9) 0.0439(9) -0.0206(7) 0.0078(9) -0.0173(9) C5 0.1051(17) 0.0643(11) 0.0319(9) -0.0157(8) 0.0089(10) -0.0228(12) C6 0.0548(10) 0.0762(11) 0.0311(7) -0.0255(7) -0.0002(7) -0.0165(9) C7 0.0942(14) 0.0596(9) 0.0398(8) -0.0247(7) 0.0000(9) -0.0334(10) C8 0.0982(14) 0.0529(9) 0.0330(8) -0.0192(7) -0.0006(9) -0.0280(10) C9 0.0748(13) 0.0838(11) 0.0306(7) -0.0312(6) -0.0046(8) -0.0160(10) S1 0.0437(2) 0.03218(16) 0.02961(15) -0.01567(12) -0.00260(15) -0.00338(15) O1 0.0489(6) 0.0388(5) 0.0340(5) -0.0174(4) 0.0062(5) -0.0052(5) O2 0.0481(6) 0.0423(6) 0.0509(6) -0.0206(5) -0.0119(5) 0.0007(5) O3 0.0521(6) 0.0314(5) 0.0443(5) -0.0192(4) -0.0058(5) 0.0005(5) C10 0.0524(10) 0.0427(9) 0.0382(8) -0.0089(7) -0.0022(7) -0.0071(8) C11 0.208(3) 0.0488(11) 0.0481(11) -0.0230(9) -0.0034(17) -0.0019(17) C12 0.214(4) 0.0871(16) 0.0466(12) -0.0314(11) 0.0137(18) -0.039(2) C13 0.0639(12) 0.0585(11) 0.0477(10) -0.0089(9) -0.0027(9) -0.0068(10) C14 0.1064(19) 0.0542(12) 0.0476(11) -0.0091(9) 0.0011(12) 0.0098(13) C15 0.0902(16) 0.0465(10) 0.0529(11) -0.0161(8) 0.0078(11) 0.0097(10) C16 0.0778(14) 0.0657(13) 0.0468(10) -0.0098(10) 0.0027(11) -0.0003(12) S2 0.0415(2) 0.03523(18) 0.03894(18) -0.01517(14) -0.00251(16) -0.00138(16) O4 0.0471(6) 0.0466(6) 0.0403(5) -0.0214(4) -0.0017(5) -0.0015(5) O5 0.0459(6) 0.0445(6) 0.0506(6) -0.0206(5) -0.0001(5) -0.0075(5) O6 0.0450(6) 0.0462(6) 0.0646(7) -0.0288(5) -0.0055(6) 0.0048(5) O1M 0.163(5) 0.101(3) 0.101(4) -0.012(3) 0.000(3) 0.019(3) C1M 0.082(4) 0.291(12) 0.084(5) 0.041(6) -0.003(4) 0.027(6) O1T 0.105(3) 0.086(2) 0.067(2) -0.0068(19) 0.017(2) -0.020(2) N1T 0.072(2) 0.062(2) 0.062(2) -0.0084(18) 0.0036(19) -0.0104(19) C1T 0.0556(19) 0.086(2) 0.0192(12) -0.0209(13) -0.0020(13) -0.0274(17) C2T 0.077(3) 0.102(4) 0.075(3) -0.030(3) 0.010(3) -0.021(3) C3T 0.109(4) 0.072(3) 0.086(3) -0.030(3) 0.000(3) -0.013(3) C4T 0.118(5) 0.093(4) 0.078(3) -0.030(3) 0.002(3) -0.022(4) C5T 0.064(3) 0.112(5) 0.084(4) -0.011(3) -0.001(3) 0.001(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N3 1.313(2) . ? C1 N2 1.319(2) . ? C1 N1 1.349(2) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C2 N5 1.297(3) . ? C2 N6 1.325(2) . ? C2 N4 1.345(2) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 H6A 0.8800 . ? N6 H6B 0.8800 . ? C3 C4 1.366(2) . ? C3 C8 1.403(3) . ? C3 S1 1.7694(18) . ? C4 C5 1.393(3) . ? C4 H4 0.9500 . ? C5 C6 1.345(3) . ? C5 H5 0.9500 . ? C6 C7 1.397(2) . ? C6 C9 1.493(3) . ? C7 C8 1.387(3) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C9 1.317(5) 2_576 ? C9 H9 0.9500 . ? S1 O2 1.4485(13) . ? S1 O3 1.4533(12) . ? S1 O1 1.4710(12) . ? C10 C11 1.365(4) . ? C10 C15 1.381(3) . ? C10 S2 1.7606(17) . ? C11 C12 1.414(3) . ? C11 H11 0.9500 . ? C12 C13 1.355(4) . ? C12 H12 0.9500 . ? C13 C14 1.389(4) . ? C13 C16 1.493(3) . ? C14 C15 1.381(3) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 C16 1.352(5) 2_856 ? C16 H16 0.9500 . ? S2 O5 1.4589(14) . ? S2 O4 1.4597(15) . ? S2 O6 1.4637(14) . ? O1M C1M 1.558(11) . ? O1M H1M 0.8400 . ? C1M H1M1 0.9800 . ? C1M H1M2 0.9800 . ? C1M H1M3 0.9800 . ? O1T N1T 1.282(6) . ? N1T C1T 1.695(4) . ? N1T C5T 1.738(6) . ? C1T C2T 1.674(6) . ? C2T C3T 1.458(7) . ? C3T C4T 1.437(7) . ? C4T C5T 1.661(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C1 N2 120.30(16) . . ? N3 C1 N1 120.33(16) . . ? N2 C1 N1 119.37(17) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? N5 C2 N6 121.00(18) . . ? N5 C2 N4 119.28(17) . . ? N6 C2 N4 119.70(17) . . ? C2 N4 H4A 120.0 . . ? C2 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C2 N5 H5A 120.0 . . ? C2 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C2 N6 H6A 120.0 . . ? C2 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? C4 C3 C8 120.67(18) . . ? C4 C3 S1 120.94(16) . . ? C8 C3 S1 118.36(12) . . ? C3 C4 C5 118.2(2) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? C6 C5 C4 123.42(18) . . ? C6 C5 H5 118.3 . . ? C4 C5 H5 118.3 . . ? C5 C6 C7 117.95(19) . . ? C5 C6 C9 120.85(17) . . ? C7 C6 C9 121.2(2) . . ? C8 C7 C6 121.0(2) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C3 118.75(16) . . ? C7 C8 H8 120.6 . . ? C3 C8 H8 120.6 . . ? C9 C9 C6 124.9(2) 2_576 . ? C9 C9 H9 117.5 2_576 . ? C6 C9 H9 117.5 . . ? O2 S1 O3 112.85(8) . . ? O2 S1 O1 111.55(7) . . ? O3 S1 O1 112.42(7) . . ? O2 S1 C3 107.01(8) . . ? O3 S1 C3 106.30(7) . . ? O1 S1 C3 106.18(8) . . ? C11 C10 C15 119.95(18) . . ? C11 C10 S2 118.97(16) . . ? C15 C10 S2 121.08(17) . . ? C10 C11 C12 118.9(2) . . ? C10 C11 H11 120.5 . . ? C12 C11 H11 120.5 . . ? C13 C12 C11 121.7(3) . . ? C13 C12 H12 119.1 . . ? C11 C12 H12 119.1 . . ? C12 C13 C14 118.2(2) . . ? C12 C13 C16 124.7(2) . . ? C14 C13 C16 117.0(2) . . ? C15 C14 C13 120.9(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C10 C15 C14 120.1(2) . . ? C10 C15 H15 119.9 . . ? C14 C15 H15 119.9 . . ? C16 C16 C13 122.1(3) 2_856 . ? C16 C16 H16 119.0 2_856 . ? C13 C16 H16 119.0 . . ? O5 S2 O4 112.22(8) . . ? O5 S2 O6 112.72(8) . . ? O4 S2 O6 112.26(8) . . ? O5 S2 C10 106.49(9) . . ? O4 S2 C10 106.40(9) . . ? O6 S2 C10 106.19(9) . . ? C1M O1M H1M 109.5 . . ? O1M C1M H1M1 109.5 . . ? O1M C1M H1M2 109.5 . . ? H1M1 C1M H1M2 109.5 . . ? O1M C1M H1M3 109.5 . . ? H1M1 C1M H1M3 109.5 . . ? H1M2 C1M H1M3 109.5 . . ? O1T N1T C1T 109.5(3) . . ? O1T N1T C5T 115.2(3) . . ? C1T N1T C5T 130.6(3) . . ? C2T C1T N1T 97.0(3) . . ? C3T C2T C1T 115.6(4) . . ? C4T C3T C2T 115.4(5) . . ? C3T C4T C5T 125.5(5) . . ? C4T C5T N1T 95.7(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 C8 C3 C4 C5 -0.5(3) . . . . ? S1 C3 C4 C5 -178.87(18) . . . . ? C3 C4 C5 C6 1.5(4) . . . . ? C4 C5 C6 C7 -1.2(4) . . . . ? C4 C5 C6 C9 179.4(2) . . . . ? C5 C6 C7 C8 0.1(4) . . . . ? C9 C6 C7 C8 179.4(2) . . . . ? C6 C7 C8 C3 0.8(4) . . . . ? C4 C3 C8 C7 -0.5(3) . . . . ? S1 C3 C8 C7 177.85(18) . . . . ? C5 C6 C9 C9 -167.0(3) . . . 2_576 ? C7 C6 C9 C9 13.7(4) . . . 2_576 ? C4 C3 S1 O2 100.78(17) . . . . ? C8 C3 S1 O2 -77.60(17) . . . . ? C4 C3 S1 O3 -20.05(19) . . . . ? C8 C3 S1 O3 161.56(16) . . . . ? C4 C3 S1 O1 -139.96(17) . . . . ? C8 C3 S1 O1 41.66(18) . . . . ? C15 C10 C11 C12 3.9(5) . . . . ? S2 C10 C11 C12 -176.1(3) . . . . ? C10 C11 C12 C13 -3.1(6) . . . . ? C11 C12 C13 C14 -1.0(5) . . . . ? C11 C12 C13 C16 -176.6(3) . . . . ? C12 C13 C14 C15 4.4(4) . . . . ? C16 C13 C14 C15 -179.7(3) . . . . ? C11 C10 C15 C14 -0.6(4) . . . . ? S2 C10 C15 C14 179.4(2) . . . . ? C13 C14 C15 C10 -3.7(4) . . . . ? C12 C13 C16 C16 -11.8(5) . . . 2_856 ? C14 C13 C16 C16 172.7(3) . . . 2_856 ? C11 C10 S2 O5 71.1(3) . . . . ? C15 C10 S2 O5 -108.9(2) . . . . ? C11 C10 S2 O4 -169.0(2) . . . . ? C15 C10 S2 O4 11.0(2) . . . . ? C11 C10 S2 O6 -49.3(3) . . . . ? C15 C10 S2 O6 130.73(19) . . . . ? O1T N1T C1T C2T 163.1(4) . . . . ? C5T N1T C1T C2T 9.4(5) . . . . ? N1T C1T C2T C3T 47.9(5) . . . . ? C1T C2T C3T C4T -67.7(7) . . . . ? C2T C3T C4T C5T 19.4(9) . . . . ? C3T C4T C5T N1T 27.7(8) . . . . ? O1T N1T C5T C4T 164.8(5) . . . . ? C1T N1T C5T C4T -42.7(6) . . . . ? 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 N1 H1A O5 0.88 2.21 2.997(2) 148.4 2_866 N1 H1B O6 0.88 2.20 2.969(2) 145.6 2_766 N2 H2A O1 0.88 2.15 2.9439(18) 149.7 2_676 N2 H2B O4 0.88 1.99 2.865(2) 171.4 2_766 N3 H3A O2 0.88 2.29 3.0282(18) 141.4 2_676 N3 H3A O1 0.88 2.63 3.174(2) 121.3 1_656 N3 H3B O4 0.88 2.00 2.8686(19) 169.1 2_866 N4 H4A O3 0.88 2.09 2.9615(19) 169.3 . N4 H4B O6 0.88 2.04 2.916(2) 170.2 1_455 N5 H5A O2 0.88 2.03 2.898(2) 167.4 1_655 N5 H5B O1 0.88 2.09 2.933(2) 161.1 . N6 H6A O3 0.88 2.10 2.968(2) 171.0 1_655 N6 H6B O5 0.88 2.04 2.908(2) 167.2 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 2.579 _refine_diff_density_min -0.545 _refine_diff_density_rms 0.172 # Attachment '- GDS 5.cif' data_GDS_5 _database_code_depnum_ccdc_archive 'CCDC 802083' #TrackingRef '- GDS 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H30 N4 O5 S' _chemical_formula_weight 402.51 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 Aba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x, y+1/2, z+1/2' '-x, -y+1/2, z+1/2' 'x+1/2, -y+1, z+1/2' '-x+1/2, y+1, z+1/2' _cell_length_a 13.1747(10) _cell_length_b 27.939(2) _cell_length_c 12.1826(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4484.3(6) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9816 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 26.10 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.54 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.192 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1728 _exptl_absorpt_coefficient_mu 0.176 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9109 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 63016 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0117 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -35 _diffrn_reflns_limit_k_max 35 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 26.71 _reflns_number_total 4723 _reflns_number_gt 4329 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0686P)^2^+1.4695P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(7) _refine_ls_number_reflns 4723 _refine_ls_number_parameters 249 _refine_ls_number_restraints 79 _refine_ls_R_factor_all 0.0418 _refine_ls_R_factor_gt 0.0371 _refine_ls_wR_factor_ref 0.1096 _refine_ls_wR_factor_gt 0.1042 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.64953(16) 0.76767(7) 0.37607(16) 0.0463(4) Uani 1 1 d . . . N1 N 0.66268(15) 0.75518(7) 0.47993(16) 0.0576(5) Uani 1 1 d . . . H1A H 0.7182 0.7638 0.5150 0.069 Uiso 1 1 calc R . . H1B H 0.6159 0.7383 0.5139 0.069 Uiso 1 1 calc R . . N2 N 0.56625(14) 0.75487(7) 0.32375(16) 0.0560(4) Uani 1 1 d . . . H2A H 0.5574 0.7632 0.2548 0.067 Uiso 1 1 calc R . . H2B H 0.5195 0.7380 0.3578 0.067 Uiso 1 1 calc R . . N3 N 0.71976(15) 0.79296(7) 0.32580(16) 0.0571(5) Uani 1 1 d . . . H3A H 0.7113 0.8014 0.2568 0.069 Uiso 1 1 calc R . . H3B H 0.7752 0.8014 0.3611 0.069 Uiso 1 1 calc R . . C2 C 0.94678(13) 0.87648(6) 0.54962(16) 0.0401(3) Uani 1 1 d . . . C3 C 0.87219(13) 0.90863(7) 0.51860(15) 0.0440(4) Uani 1 1 d . . . H3 H 0.8070 0.8974 0.4975 0.053 Uiso 1 1 calc R . . C4 C 0.89307(14) 0.95704(7) 0.51854(15) 0.0431(4) Uani 1 1 d . . . H4 H 0.8418 0.9791 0.4976 0.052 Uiso 1 1 calc R . . C5 C 0.98881(12) 0.97396(6) 0.54897(16) 0.0394(3) Uani 1 1 d . . . C6 C 1.06300(14) 0.94102(7) 0.58010(17) 0.0431(4) Uani 1 1 d . . . H6 H 1.1282 0.9521 0.6017 0.052 Uiso 1 1 calc R . . C7 C 1.04244(13) 0.89203(7) 0.57983(16) 0.0423(4) Uani 1 1 d . . . H7 H 1.0934 0.8697 0.6001 0.051 Uiso 1 1 calc R . . S1 S 0.91851(3) 0.814696(16) 0.54569(4) 0.04328(12) Uani 1 1 d . . . O1 O 0.81912(11) 0.80930(5) 0.59719(12) 0.0514(4) Uani 1 1 d . . . O2 O 0.99861(12) 0.79022(5) 0.60514(12) 0.0515(3) Uani 1 1 d . . . O3 O 0.91512(11) 0.80151(6) 0.42993(13) 0.0510(3) Uani 1 1 d . . . C8 C 0.0245(2) 0.89895(13) 0.1353(2) 0.0818(9) Uani 1 1 d U . . C9 C -0.06217(18) 0.92414(14) 0.0766(2) 0.0782(9) Uani 1 1 d U . . H9A H -0.1267 0.9146 0.1121 0.094 Uiso 1 1 calc R . . H9B H -0.0541 0.9591 0.0872 0.094 Uiso 1 1 calc R . . C10 C -0.07084(17) 0.91441(10) -0.04407(19) 0.0587(6) Uani 1 1 d U . . H10 H -0.0866 0.8797 -0.0546 0.070 Uiso 1 1 calc R . . C11 C 0.02596(17) 0.92517(10) -0.0997(2) 0.0597(6) Uani 1 1 d U . . H11A H 0.0396 0.9599 -0.0933 0.072 Uiso 1 1 calc R . . H11B H 0.0187 0.9177 -0.1788 0.072 Uiso 1 1 calc R . . C12 C 0.11868(19) 0.89732(12) -0.0539(2) 0.0715(7) Uani 1 1 d U . . C13 C -0.1791(2) 0.93434(14) -0.1940(2) 0.0817(9) Uani 1 1 d U . . H13A H -0.1240 0.9460 -0.2409 0.123 Uiso 1 1 calc R . . H13B H -0.2415 0.9520 -0.2106 0.123 Uiso 1 1 calc R . . H13C H -0.1900 0.9002 -0.2076 0.123 Uiso 1 1 calc R . . C14 C 0.1226(4) 0.84681(18) -0.0907(5) 0.142(2) Uani 1 1 d U . . H14A H 0.1838 0.8315 -0.0613 0.213 Uiso 1 1 calc R . . H14B H 0.1242 0.8457 -0.1711 0.213 Uiso 1 1 calc R . . H14C H 0.0624 0.8298 -0.0640 0.213 Uiso 1 1 calc R . . C15 C 0.2111(2) 0.92421(18) -0.0944(3) 0.1041(13) Uani 1 1 d U . . H15A H 0.2727 0.9071 -0.0720 0.156 Uiso 1 1 calc R . . H15B H 0.2116 0.9565 -0.0628 0.156 Uiso 1 1 calc R . . H15C H 0.2089 0.9265 -0.1747 0.156 Uiso 1 1 calc R . . C16 C 0.0445(3) 0.9229(3) 0.2438(3) 0.165(3) Uani 1 1 d U . . H16A H 0.0754 0.8998 0.2944 0.247 Uiso 1 1 calc R . . H16B H -0.0196 0.9345 0.2748 0.247 Uiso 1 1 calc R . . H16C H 0.0909 0.9499 0.2330 0.247 Uiso 1 1 calc R . . C17 C -0.0053(4) 0.8487(2) 0.1607(5) 0.166(3) Uani 1 1 d U . . H17A H -0.0075 0.8301 0.0926 0.249 Uiso 1 1 calc R . . H17B H -0.0725 0.8485 0.1952 0.249 Uiso 1 1 calc R . . H17C H 0.0445 0.8346 0.2109 0.249 Uiso 1 1 calc R . . N4 N 0.11764(14) 0.90107(9) 0.06829(18) 0.0668(5) Uani 1 1 d U . . O4 O 0.20148(15) 0.89045(11) 0.1169(2) 0.0992(8) Uani 1 1 d U . . O5 O -0.15293(12) 0.94136(8) -0.08264(14) 0.0718(5) Uani 1 1 d U . . 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 0.0498(11) 0.0467(10) 0.0425(10) -0.0026(8) 0.0002(8) -0.0012(8) N1 0.0562(10) 0.0739(12) 0.0429(10) 0.0049(8) -0.0041(8) -0.0158(9) N2 0.0589(10) 0.0662(11) 0.0429(9) 0.0067(8) -0.0041(8) -0.0159(9) N3 0.0557(11) 0.0706(11) 0.0451(9) 0.0056(8) -0.0050(8) -0.0179(9) C2 0.0392(8) 0.0501(8) 0.0308(7) 0.0000(8) 0.0013(8) 0.0008(6) C3 0.0324(8) 0.0605(11) 0.0389(10) 0.0010(8) -0.0050(7) -0.0015(7) C4 0.0331(8) 0.0549(10) 0.0412(10) 0.0018(8) -0.0036(7) 0.0048(7) C5 0.0351(8) 0.0533(9) 0.0299(7) 0.0002(8) 0.0007(7) 0.0009(7) C6 0.0331(8) 0.0561(10) 0.0400(9) -0.0004(8) -0.0025(7) -0.0001(7) C7 0.0337(8) 0.0545(10) 0.0389(9) 0.0007(7) -0.0010(7) 0.0049(7) S1 0.0430(2) 0.0506(2) 0.0363(2) -0.0006(2) 0.0008(2) -0.00044(17) O1 0.0471(8) 0.0618(8) 0.0451(8) -0.0006(7) 0.0053(6) -0.0091(6) O2 0.0548(8) 0.0527(7) 0.0469(8) 0.0059(6) -0.0009(6) 0.0052(6) O3 0.0508(8) 0.0597(8) 0.0426(8) -0.0083(7) -0.0010(6) 0.0023(6) C8 0.0637(16) 0.132(3) 0.0503(14) 0.0292(16) -0.0034(12) -0.0081(16) C9 0.0420(11) 0.155(3) 0.0380(12) 0.0066(14) 0.0044(9) -0.0172(14) C10 0.0539(13) 0.0793(15) 0.0430(12) 0.0051(11) -0.0007(9) -0.0064(11) C11 0.0474(12) 0.0885(16) 0.0431(11) -0.0040(11) 0.0019(9) -0.0033(11) C12 0.0485(12) 0.116(2) 0.0506(13) -0.0121(13) -0.0025(10) 0.0089(14) C13 0.0691(16) 0.130(3) 0.0458(14) 0.0048(14) -0.0072(12) 0.0079(17) C14 0.159(4) 0.124(3) 0.142(4) -0.056(3) -0.047(4) 0.053(3) C15 0.0529(15) 0.201(4) 0.0585(17) -0.001(2) 0.0097(13) -0.002(2) C16 0.067(2) 0.387(9) 0.0399(16) 0.007(3) -0.0061(14) 0.021(3) C17 0.126(4) 0.194(5) 0.180(5) 0.127(5) -0.034(4) -0.053(4) N4 0.0461(9) 0.1015(15) 0.0529(12) 0.0062(11) -0.0073(9) -0.0079(10) O4 0.0546(11) 0.171(2) 0.0717(13) 0.0144(14) -0.0174(10) 0.0077(12) O5 0.0415(8) 0.1314(16) 0.0425(9) 0.0001(9) 0.0001(7) 0.0017(9) _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 N3 1.315(3) . ? C1 N2 1.318(3) . ? C1 N1 1.324(3) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C2 C7 1.383(2) . ? C2 C3 1.384(3) . ? C2 S1 1.7665(18) . ? C3 C4 1.380(3) . ? C3 H3 0.9500 . ? C4 C5 1.397(2) . ? C4 H4 0.9500 . ? C5 C6 1.395(3) . ? C5 C5 1.485(3) 2_775 ? C6 C7 1.395(3) . ? C6 H6 0.9500 . ? C7 H7 0.9500 . ? S1 O2 1.4511(15) . ? S1 O3 1.4583(16) . ? S1 O1 1.4598(15) . ? C8 N4 1.475(4) . ? C8 C17 1.489(5) . ? C8 C16 1.505(5) . ? C8 C9 1.520(4) . ? C9 C10 1.499(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O5 1.399(3) . ? C10 C11 1.475(3) . ? C10 H10 1.0000 . ? C11 C12 1.552(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 C14 1.482(5) . ? C12 N4 1.492(3) . ? C12 C15 1.513(4) . ? C13 O5 1.413(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 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? N4 O4 1.288(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N3 C1 N2 120.40(19) . . ? N3 C1 N1 119.6(2) . . ? N2 C1 N1 120.0(2) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C7 C2 C3 121.05(17) . . ? C7 C2 S1 120.43(14) . . ? C3 C2 S1 118.50(14) . . ? C4 C3 C2 119.65(17) . . ? C4 C3 H3 120.2 . . ? C2 C3 H3 120.2 . . ? C3 C4 C5 120.76(17) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 118.77(17) . . ? C6 C5 C5 120.50(18) . 2_775 ? C4 C5 C5 120.72(18) . 2_775 ? C5 C6 C7 120.70(17) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C2 C7 C6 119.06(17) . . ? C2 C7 H7 120.5 . . ? C6 C7 H7 120.5 . . ? O2 S1 O3 112.70(9) . . ? O2 S1 O1 112.90(9) . . ? O3 S1 O1 111.22(9) . . ? O2 S1 C2 107.07(9) . . ? O3 S1 C2 106.23(9) . . ? O1 S1 C2 106.17(8) . . ? N4 C8 C17 111.8(4) . . ? N4 C8 C16 108.8(3) . . ? C17 C8 C16 106.4(4) . . ? N4 C8 C9 110.3(2) . . ? C17 C8 C9 109.6(3) . . ? C16 C8 C9 109.9(3) . . ? C10 C9 C8 115.8(3) . . ? C10 C9 H9A 108.3 . . ? C8 C9 H9A 108.3 . . ? C10 C9 H9B 108.3 . . ? C8 C9 H9B 108.3 . . ? H9A C9 H9B 107.4 . . ? O5 C10 C11 113.8(2) . . ? O5 C10 C9 106.9(2) . . ? C11 C10 C9 110.4(2) . . ? O5 C10 H10 108.5 . . ? C11 C10 H10 108.5 . . ? C9 C10 H10 108.5 . . ? C10 C11 C12 114.4(2) . . ? C10 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C10 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C14 C12 N4 111.6(3) . . ? C14 C12 C15 110.3(4) . . ? N4 C12 C15 107.3(2) . . ? C14 C12 C11 113.3(3) . . ? N4 C12 C11 108.4(2) . . ? C15 C12 C11 105.5(3) . . ? O5 C13 H13A 109.5 . . ? O5 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O5 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C8 C16 H16A 109.5 . . ? C8 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C8 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C8 C17 H17A 109.5 . . ? C8 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C8 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O4 N4 C8 116.8(2) . . ? O4 N4 C12 115.8(2) . . ? C8 N4 C12 123.8(2) . . ? C10 O5 C13 115.9(2) . . ? 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 C7 C2 C3 C4 -0.5(3) . . . . ? S1 C2 C3 C4 -178.54(14) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C3 C4 C5 C6 -0.4(3) . . . . ? C3 C4 C5 C5 -179.95(13) . . . 2_775 ? C4 C5 C6 C7 0.6(3) . . . . ? C5 C5 C6 C7 -179.76(14) 2_775 . . . ? C3 C2 C7 C6 0.8(3) . . . . ? S1 C2 C7 C6 178.78(15) . . . . ? C5 C6 C7 C2 -0.9(3) . . . . ? C7 C2 S1 O2 15.02(18) . . . . ? C3 C2 S1 O2 -166.95(15) . . . . ? C7 C2 S1 O3 -105.63(17) . . . . ? C3 C2 S1 O3 72.40(17) . . . . ? C7 C2 S1 O1 135.88(16) . . . . ? C3 C2 S1 O1 -46.09(18) . . . . ? N4 C8 C9 C10 42.6(4) . . . . ? C17 C8 C9 C10 -81.0(4) . . . . ? C16 C8 C9 C10 162.5(3) . . . . ? C8 C9 C10 O5 -178.8(2) . . . . ? C8 C9 C10 C11 -54.5(4) . . . . ? O5 C10 C11 C12 177.2(2) . . . . ? C9 C10 C11 C12 57.0(3) . . . . ? C10 C11 C12 C14 77.0(4) . . . . ? C10 C11 C12 N4 -47.6(3) . . . . ? C10 C11 C12 C15 -162.3(3) . . . . ? C17 C8 N4 O4 -72.1(4) . . . . ? C16 C8 N4 O4 45.0(5) . . . . ? C9 C8 N4 O4 165.6(3) . . . . ? C17 C8 N4 C12 85.3(4) . . . . ? C16 C8 N4 C12 -157.5(4) . . . . ? C9 C8 N4 C12 -37.0(4) . . . . ? C14 C12 N4 O4 71.1(4) . . . . ? C15 C12 N4 O4 -49.8(4) . . . . ? C11 C12 N4 O4 -163.3(2) . . . . ? C14 C12 N4 C8 -86.5(4) . . . . ? C15 C12 N4 C8 152.6(3) . . . . ? C11 C12 N4 C8 39.1(4) . . . . ? C11 C10 O5 C13 62.6(3) . . . . ? C9 C10 O5 C13 -175.3(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 N1 H1A O1 0.88 2.09 2.928(2) 157.7 . N1 H1B O2 0.88 2.06 2.934(2) 170.1 3_465 N2 H2A O2 0.88 2.11 2.966(2) 165.5 8_644 N2 H2B O3 0.88 1.97 2.849(2) 178.0 3_465 N3 H3A O1 0.88 2.00 2.868(3) 169.9 8_644 N3 H3B O3 0.88 2.03 2.879(2) 163.4 . _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.71 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.412 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.036 # Attachment '- GDS 6.cif' data_GDS_6 _database_code_depnum_ccdc_archive 'CCDC 802084' #TrackingRef '- GDS 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C39 H64 N17 O15 S4' _chemical_formula_weight 1139.31 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 7.3720(16) _cell_length_b 16.324(4) _cell_length_c 24.346(5) _cell_angle_alpha 72.595(4) _cell_angle_beta 89.618(4) _cell_angle_gamma 85.998(4) _cell_volume 2788.5(10) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 1453 _cell_measurement_theta_min 2.48 _cell_measurement_theta_max 23.44 _exptl_crystal_description slab _exptl_crystal_colour orange _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1202 _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9616 _exptl_absorpt_correction_T_max 0.9805 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 20511 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0857 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 0.88 _diffrn_reflns_theta_max 26.50 _reflns_number_total 11490 _reflns_number_gt 6288 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0916P)^2^+0.9126P] 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 20511 _refine_ls_number_parameters 684 _refine_ls_number_restraints 90 _refine_ls_R_factor_all 0.1498 _refine_ls_R_factor_gt 0.0713 _refine_ls_wR_factor_ref 0.2144 _refine_ls_wR_factor_gt 0.1732 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _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 0.9727(3) 0.04947(13) 0.11977(9) 0.0337(6) Uani 1 1 d . . . N1 N 1.1279(2) 0.04711(11) 0.09290(8) 0.0389(5) Uani 1 1 d . . . H1A H 1.1284 0.0442 0.0574 0.047 Uiso 1 1 calc R . . H1B H 1.2311 0.0485 0.1105 0.047 Uiso 1 1 calc R . . N2 N 0.8186(2) 0.04739(11) 0.09326(8) 0.0384(5) Uani 1 1 d . . . H2A H 0.8196 0.0444 0.0578 0.046 Uiso 1 1 calc R . . H2B H 0.7147 0.0489 0.1111 0.046 Uiso 1 1 calc R . . N3 N 0.9708(3) 0.05188(13) 0.17389(8) 0.0484(6) Uani 1 1 d . . . H3A H 1.0737 0.0519 0.1920 0.058 Uiso 1 1 calc R . . H3B H 0.8667 0.0534 0.1916 0.058 Uiso 1 1 calc R . . C2 C 0.4539(3) 0.14032(14) 0.34948(9) 0.0371(6) Uani 1 1 d . . . N4 N 0.4516(3) 0.13959(13) 0.40410(8) 0.0498(6) Uani 1 1 d . . . H4A H 0.5537 0.1419 0.4219 0.060 Uiso 1 1 calc R . . H4B H 0.3480 0.1368 0.4225 0.060 Uiso 1 1 calc R . . N5 N 0.6097(2) 0.14454(11) 0.32212(8) 0.0401(5) Uani 1 1 d . . . H5A H 0.6115 0.1464 0.2856 0.048 Uiso 1 1 calc R . . H5B H 0.7118 0.1455 0.3404 0.048 Uiso 1 1 calc R . . N6 N 0.2995(3) 0.13884(12) 0.32237(8) 0.0402(5) Uani 1 1 d . . . H6A H 0.3004 0.1407 0.2859 0.048 Uiso 1 1 calc R . . H6B H 0.1960 0.1360 0.3408 0.048 Uiso 1 1 calc R . . C3 C 0.5048(3) 0.86372(14) 0.15139(10) 0.0381(6) Uani 1 1 d . . . N7 N 0.6588(3) 0.86189(12) 0.17871(8) 0.0429(6) Uani 1 1 d . . . H7A H 0.6583 0.8595 0.2153 0.052 Uiso 1 1 calc R . . H7B H 0.7624 0.8631 0.1604 0.052 Uiso 1 1 calc R . . N8 N 0.5053(3) 0.86551(14) 0.09624(8) 0.0550(6) Uani 1 1 d . . . H8A H 0.6089 0.8655 0.0781 0.066 Uiso 1 1 calc R . . H8B H 0.4020 0.8667 0.0780 0.066 Uiso 1 1 calc R . . N9 N 0.3481(3) 0.86194(11) 0.17832(8) 0.0409(5) Uani 1 1 d . . . H9A H 0.3463 0.8595 0.2149 0.049 Uiso 1 1 calc R . . H9B H 0.2457 0.8632 0.1597 0.049 Uiso 1 1 calc R . . C4 C 0.9853(3) 0.95688(13) 0.37883(9) 0.0331(6) Uani 1 1 d . . . N10 N 0.9831(3) 0.95501(13) 0.32487(8) 0.0490(6) Uani 1 1 d . . . H10A H 1.0858 0.9543 0.3063 0.059 Uiso 1 1 calc R . . H10B H 0.8791 0.9545 0.3075 0.059 Uiso 1 1 calc R . . N11 N 1.1388(2) 0.95766(11) 0.40508(8) 0.0368(5) Uani 1 1 d . . . H11A H 1.2422 0.9569 0.3869 0.044 Uiso 1 1 calc R . . H11B H 1.1389 0.9589 0.4410 0.044 Uiso 1 1 calc R . . N12 N 0.8297(2) 0.95894(11) 0.40641(8) 0.0390(5) Uani 1 1 d . . . H12A H 0.8304 0.9608 0.4422 0.047 Uiso 1 1 calc R . . H12B H 0.7258 0.9584 0.3889 0.047 Uiso 1 1 calc R . . C5 C 0.4630(3) 0.23146(15) 0.11984(10) 0.0426(7) Uani 1 1 d . . . C6 C 0.4421(4) 0.23898(16) 0.06233(11) 0.0544(8) Uani 1 1 d . . . H6 H 0.4241 0.1896 0.0506 0.065 Uiso 1 1 calc R . . C7 C 0.4475(4) 0.31859(18) 0.02186(12) 0.0640(9) Uani 1 1 d . . . H7 H 0.4331 0.3239 -0.0178 0.077 Uiso 1 1 calc R . . C8 C 0.4735(4) 0.38991(17) 0.03843(12) 0.0543(8) Uani 1 1 d . . . C9 C 0.4933(4) 0.38322(17) 0.09537(13) 0.0690(10) Uani 1 1 d . . . H9 H 0.5111 0.4329 0.1068 0.083 Uiso 1 1 calc R . . C10 C 0.4871(5) 0.30341(17) 0.13635(12) 0.0693(10) Uani 1 1 d . . . H10 H 0.4995 0.2985 0.1760 0.083 Uiso 1 1 calc R . . N13 N 0.4821(3) 0.46961(13) -0.00827(10) 0.0630(8) Uani 1 1 d . . . S1 S 0.46121(8) 0.13027(4) 0.17290(2) 0.03720(15) Uani 1 1 d . . . O1 O 0.6215(2) 0.12269(10) 0.20870(7) 0.0423(4) Uani 1 1 d . . . O2 O 0.4675(2) 0.06618(9) 0.14215(6) 0.0407(4) Uani 1 1 d . . . O3 O 0.2939(2) 0.13157(10) 0.20462(7) 0.0434(5) Uani 1 1 d . . . C11 C 0.9670(3) 0.25667(13) 0.45072(10) 0.0360(6) Uani 1 1 d . . . C12 C 0.9191(4) 0.33045(16) 0.40735(11) 0.0583(8) Uani 1 1 d . . . H12 H 0.8840 0.3275 0.3706 0.070 Uiso 1 1 calc R . . C13 C 0.9224(4) 0.41001(16) 0.41762(12) 0.0646(9) Uani 1 1 d . . . H13 H 0.8860 0.4614 0.3881 0.078 Uiso 1 1 calc R . . C14 C 0.9785(3) 0.41404(15) 0.47072(11) 0.0480(7) Uani 1 1 d . . . C15 C 1.0272(4) 0.34011(15) 0.51389(12) 0.0563(8) Uani 1 1 d . . . H15 H 1.0644 0.3429 0.5505 0.068 Uiso 1 1 calc R . . C16 C 1.0219(4) 0.26130(15) 0.50375(11) 0.0530(8) Uani 1 1 d . . . H16 H 1.0563 0.2099 0.5335 0.064 Uiso 1 1 calc R . . N14 N 0.9775(3) 0.49945(12) 0.47578(8) 0.0537(6) Uani 1 1 d . . . S2 S 0.95387(8) 0.15459(3) 0.44025(2) 0.03388(15) Uani 1 1 d . . . O4 O 0.9493(2) 0.16914(9) 0.37828(6) 0.0384(4) Uani 1 1 d . . . O5 O 1.1144(2) 0.10233(9) 0.46826(6) 0.0390(4) Uani 1 1 d . . . O6 O 0.7871(2) 0.12114(10) 0.46797(6) 0.0411(4) Uani 1 1 d . . . C17 C 0.0057(3) 0.74332(13) 0.05054(10) 0.0343(6) Uani 1 1 d . . . C18 C 0.0650(4) 0.73288(15) -0.00110(10) 0.0490(7) Uani 1 1 d . . . H18 H 0.1106 0.7800 -0.0297 0.059 Uiso 1 1 calc R . . C19 C 0.0584(4) 0.65478(15) -0.01125(11) 0.0540(7) Uani 1 1 d . . . H19 H 0.0979 0.6480 -0.0470 0.065 Uiso 1 1 calc R . . C20 C -0.0059(3) 0.58632(15) 0.03066(11) 0.0477(7) Uani 1 1 d . . . C21 C -0.0634(4) 0.59563(16) 0.08218(12) 0.0621(9) Uani 1 1 d . . . H21 H -0.1072 0.5481 0.1109 0.075 Uiso 1 1 calc R . . C22 C -0.0577(4) 0.67476(15) 0.09251(11) 0.0552(8) Uani 1 1 d . . . H22 H -0.0972 0.6814 0.1282 0.066 Uiso 1 1 calc R . . N15 N -0.0167(3) 0.50146(13) 0.02471(8) 0.0550(7) Uani 1 1 d . . . S3 S 0.00640(8) 0.84568(3) 0.06142(2) 0.03487(15) Uani 1 1 d . . . O7 O 0.1686(2) 0.88384(9) 0.03368(6) 0.0421(4) Uani 1 1 d . . . O8 O -0.1590(2) 0.89353(10) 0.03368(6) 0.0427(5) Uani 1 1 d . . . O9 O 0.0078(2) 0.83101(9) 0.12355(6) 0.0404(4) Uani 1 1 d . . . C23 C 0.5045(3) 0.77142(14) 0.38233(10) 0.0377(6) Uani 1 1 d . . . C24 C 0.5465(4) 0.69778(17) 0.36719(12) 0.0632(9) Uani 1 1 d . . . H24 H 0.5770 0.7017 0.3286 0.076 Uiso 1 1 calc R . . C25 C 0.5444(4) 0.61758(17) 0.40826(13) 0.0694(10) Uani 1 1 d . . . H25 H 0.5729 0.5667 0.3977 0.083 Uiso 1 1 calc R . . C26 C 0.5016(3) 0.61207(16) 0.46354(12) 0.0499(8) Uani 1 1 d . . . C27 C 0.4644(4) 0.68536(17) 0.47882(12) 0.0600(9) Uani 1 1 d . . . H27 H 0.4377 0.6812 0.5177 0.072 Uiso 1 1 calc R . . C28 C 0.4652(4) 0.76520(16) 0.43854(11) 0.0520(8) Uani 1 1 d . . . H28 H 0.4386 0.8158 0.4496 0.062 Uiso 1 1 calc R . . N16 N 0.4949(3) 0.53186(12) 0.50869(10) 0.0562(7) Uani 1 1 d . . . S4 S 0.49874(8) 0.87225(4) 0.32825(2) 0.03625(15) Uani 1 1 d . . . O10 O 0.6641(2) 0.87176(10) 0.29556(7) 0.0429(5) Uani 1 1 d . . . O11 O 0.3351(2) 0.87733(10) 0.29375(7) 0.0424(5) Uani 1 1 d . . . O12 O 0.4907(2) 0.93742(9) 0.35828(6) 0.0393(4) Uani 1 1 d . . . C1T C 0.4316(5) 0.5853(2) 0.20421(18) 0.1028(14) Uani 1 1 d U . . C2T C 0.2557(6) 0.6224(2) 0.22380(18) 0.1172(16) Uani 1 1 d U . . H2T1 H 0.2656 0.6849 0.2165 0.141 Uiso 1 1 calc R . . H2T2 H 0.1552 0.6157 0.1991 0.141 Uiso 1 1 calc R . . C3T C 0.2046(5) 0.5861(2) 0.28354(16) 0.0938(12) Uani 1 1 d U . . H3T H 0.3023 0.5936 0.3096 0.113 Uiso 1 1 calc R . . C4T C 0.1867(7) 0.4929(3) 0.2924(2) 0.174(2) Uani 1 1 d U . . H4T1 H 0.0961 0.4869 0.2643 0.209 Uiso 1 1 calc R . . H4T2 H 0.1385 0.4674 0.3314 0.209 Uiso 1 1 calc R . . C5T C 0.3627(9) 0.4411(3) 0.2863(2) 0.155(2) Uani 1 1 d U . . C6T C 0.0420(6) 0.7031(2) 0.3023(2) 0.149(2) Uani 1 1 d U . . H6T1 H 0.1165 0.7000 0.3361 0.223 Uiso 1 1 calc R . . H6T2 H -0.0819 0.7255 0.3072 0.223 Uiso 1 1 calc R . . H6T3 H 0.0946 0.7414 0.2679 0.223 Uiso 1 1 calc R . . C7T C 0.6004(7) 0.6141(3) 0.2275(3) 0.233(2) Uani 1 1 d U . . H7T1 H 0.6040 0.5916 0.2696 0.350 Uiso 1 1 calc R . . H7T2 H 0.5956 0.6771 0.2158 0.350 Uiso 1 1 calc R . . H7T3 H 0.7097 0.5921 0.2119 0.350 Uiso 1 1 calc R . . C8T C 0.4382(7) 0.6061(3) 0.1417(2) 0.166(2) Uani 1 1 d U . . H8T1 H 0.5561 0.5848 0.1307 0.248 Uiso 1 1 calc R . . H8T2 H 0.4222 0.6686 0.1244 0.248 Uiso 1 1 calc R . . H8T3 H 0.3407 0.5788 0.1281 0.248 Uiso 1 1 calc R . . C9T C 0.5156(11) 0.4338(4) 0.3297(2) 0.352(4) Uani 1 1 d U . . H9T1 H 0.6254 0.4059 0.3183 0.528 Uiso 1 1 calc R . . H9T2 H 0.4789 0.3993 0.3680 0.528 Uiso 1 1 calc R . . H9T3 H 0.5408 0.4914 0.3309 0.528 Uiso 1 1 calc R . . C10T C 0.3338(11) 0.3574(3) 0.2832(3) 0.273(4) Uani 1 1 d U . . H10C H 0.4468 0.3317 0.2721 0.409 Uiso 1 1 calc R . . H10D H 0.2383 0.3614 0.2545 0.409 Uiso 1 1 calc R . . H10E H 0.2963 0.3215 0.3209 0.409 Uiso 1 1 calc R . . N1T N 0.4367(5) 0.48983(19) 0.22794(14) 0.1068(11) Uani 1 1 d U . . O1T O 0.5625(5) 0.44707(18) 0.20649(13) 0.1462(12) Uani 1 1 d U . . O2T O 0.0374(4) 0.62294(17) 0.29629(13) 0.1187(10) Uani 1 1 d U . . C1M C 0.9398(10) 0.3205(5) 0.2015(4) 0.306(4) Uani 1 1 d U . . H1M1 H 1.0698 0.3027 0.2069 0.459 Uiso 1 1 calc R . . H1M2 H 0.9067 0.3335 0.1607 0.459 Uiso 1 1 calc R . . H1M3 H 0.8692 0.2738 0.2244 0.459 Uiso 1 1 calc R . . O1M O 0.9016(11) 0.3948(4) 0.2194(4) 0.403(4) Uani 1 1 d U . . H1M H 0.8106 0.3879 0.2409 0.604 Uiso 1 1 calc RU . . 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 0.0414(12) 0.0282(11) 0.0339(12) -0.0121(9) 0.0036(10) -0.0062(10) N1 0.0342(10) 0.0512(11) 0.0361(10) -0.0209(9) 0.0012(8) -0.0014(9) N2 0.0374(10) 0.0498(11) 0.0320(10) -0.0183(9) 0.0063(8) -0.0047(9) N3 0.0381(11) 0.0782(14) 0.0338(10) -0.0239(10) 0.0005(9) -0.0068(10) C2 0.0446(13) 0.0313(12) 0.0343(12) -0.0082(10) 0.0003(10) -0.0023(10) N4 0.0384(11) 0.0729(14) 0.0410(11) -0.0204(10) 0.0019(9) -0.0092(10) N5 0.0352(10) 0.0512(11) 0.0355(10) -0.0144(9) 0.0006(8) -0.0064(9) N6 0.0381(10) 0.0488(11) 0.0334(11) -0.0114(9) 0.0003(9) -0.0045(9) C3 0.0440(13) 0.0313(12) 0.0381(13) -0.0090(10) 0.0038(11) -0.0031(10) N7 0.0406(11) 0.0527(12) 0.0361(11) -0.0142(9) 0.0022(9) -0.0042(9) N8 0.0468(12) 0.0859(15) 0.0371(11) -0.0245(11) 0.0053(10) -0.0112(11) N9 0.0388(11) 0.0477(11) 0.0364(11) -0.0121(9) -0.0002(9) -0.0067(9) C4 0.0417(12) 0.0261(11) 0.0322(12) -0.0096(9) 0.0045(10) -0.0027(10) N10 0.0375(11) 0.0779(14) 0.0372(11) -0.0255(10) 0.0007(9) -0.0051(10) N11 0.0340(10) 0.0446(10) 0.0368(10) -0.0195(8) 0.0016(8) -0.0049(8) N12 0.0390(10) 0.0447(11) 0.0374(11) -0.0179(9) -0.0012(9) -0.0053(9) C5 0.0387(13) 0.0424(13) 0.0465(14) -0.0133(11) 0.0024(11) -0.0021(11) C6 0.0721(17) 0.0450(14) 0.0458(15) -0.0106(12) -0.0093(13) -0.0141(13) C7 0.085(2) 0.0612(17) 0.0439(16) -0.0105(14) -0.0130(15) -0.0117(16) C8 0.0549(16) 0.0465(15) 0.0536(16) -0.0035(13) -0.0100(13) 0.0000(13) C9 0.104(2) 0.0436(15) 0.0642(18) -0.0223(13) -0.0003(17) -0.0108(16) C10 0.118(3) 0.0479(16) 0.0447(16) -0.0161(13) 0.0005(17) -0.0123(17) N13 0.0665(15) 0.0508(14) 0.0688(16) -0.0133(12) -0.0079(12) -0.0043(13) S1 0.0349(3) 0.0422(3) 0.0366(3) -0.0148(3) 0.0012(2) -0.0035(3) O1 0.0355(8) 0.0530(9) 0.0408(9) -0.0175(7) -0.0012(7) -0.0030(7) O2 0.0366(8) 0.0444(9) 0.0463(9) -0.0212(7) 0.0038(7) -0.0049(7) O3 0.0362(8) 0.0557(10) 0.0409(9) -0.0187(8) 0.0068(7) -0.0029(7) C11 0.0379(12) 0.0326(11) 0.0419(13) -0.0176(10) 0.0031(10) -0.0052(10) C12 0.093(2) 0.0434(14) 0.0397(14) -0.0154(12) -0.0063(14) -0.0005(15) C13 0.109(2) 0.0306(13) 0.0534(17) -0.0119(12) -0.0066(16) 0.0019(15) C14 0.0558(15) 0.0376(12) 0.0578(15) -0.0246(11) 0.0011(12) -0.0053(12) C15 0.0788(18) 0.0408(13) 0.0544(15) -0.0216(12) -0.0161(14) -0.0045(13) C16 0.0745(18) 0.0327(13) 0.0535(15) -0.0161(11) -0.0188(13) 0.0002(12) N14 0.0650(14) 0.0361(11) 0.0658(14) -0.0237(11) -0.0060(12) -0.0047(10) S2 0.0393(3) 0.0315(3) 0.0355(3) -0.0166(2) 0.0018(2) -0.0048(2) O4 0.0445(9) 0.0394(8) 0.0357(8) -0.0179(7) 0.0008(7) -0.0034(7) O5 0.0423(9) 0.0387(8) 0.0391(8) -0.0180(7) -0.0018(7) 0.0053(7) O6 0.0407(9) 0.0468(9) 0.0392(9) -0.0155(7) 0.0053(7) -0.0140(7) C17 0.0333(11) 0.0309(11) 0.0432(13) -0.0175(10) -0.0005(10) -0.0048(9) C18 0.0687(17) 0.0395(13) 0.0458(14) -0.0218(11) 0.0126(13) -0.0118(12) C19 0.0694(17) 0.0456(13) 0.0578(15) -0.0307(12) 0.0184(13) -0.0101(13) C20 0.0504(14) 0.0358(12) 0.0653(16) -0.0271(11) 0.0025(12) -0.0063(11) C21 0.100(2) 0.0394(14) 0.0539(16) -0.0201(12) 0.0183(15) -0.0232(14) C22 0.0850(19) 0.0403(13) 0.0471(15) -0.0209(11) 0.0149(14) -0.0172(13) N15 0.0647(14) 0.0418(11) 0.0661(14) -0.0274(11) 0.0056(13) -0.0070(10) S3 0.0418(3) 0.0317(3) 0.0347(3) -0.0153(2) 0.0021(2) -0.0041(2) O7 0.0481(9) 0.0417(9) 0.0408(9) -0.0163(7) 0.0074(7) -0.0158(7) O8 0.0484(9) 0.0394(9) 0.0401(9) -0.0139(7) 0.0018(8) 0.0061(8) O9 0.0501(9) 0.0412(8) 0.0335(8) -0.0157(7) 0.0034(7) -0.0073(7) C23 0.0345(12) 0.0381(12) 0.0422(13) -0.0149(10) 0.0011(10) -0.0009(10) C24 0.099(2) 0.0470(15) 0.0439(15) -0.0144(13) 0.0133(15) -0.0005(16) C25 0.102(2) 0.0374(15) 0.0676(19) -0.0172(14) 0.0066(17) 0.0092(16) C26 0.0465(14) 0.0425(14) 0.0537(16) -0.0048(13) 0.0050(13) 0.0000(12) C27 0.083(2) 0.0499(16) 0.0442(15) -0.0118(13) 0.0139(14) 0.0024(15) C28 0.0676(17) 0.0426(14) 0.0461(15) -0.0152(12) 0.0080(13) 0.0024(13) N16 0.0576(13) 0.0428(13) 0.0652(15) -0.0133(11) 0.0059(11) 0.0029(12) S4 0.0358(3) 0.0385(3) 0.0359(3) -0.0133(3) 0.0009(2) -0.0028(2) O10 0.0378(9) 0.0518(9) 0.0417(9) -0.0179(8) 0.0088(7) -0.0050(7) O11 0.0388(9) 0.0515(9) 0.0391(9) -0.0169(7) 0.0008(7) -0.0035(7) O12 0.0415(9) 0.0372(8) 0.0422(9) -0.0164(7) 0.0005(7) -0.0038(7) C1T 0.098(3) 0.073(2) 0.140(3) -0.038(2) 0.033(2) -0.003(2) C2T 0.153(4) 0.065(2) 0.121(3) -0.012(2) 0.038(3) 0.006(2) C3T 0.105(3) 0.087(2) 0.095(2) -0.038(2) 0.019(2) 0.000(2) C4T 0.241(5) 0.070(3) 0.194(4) -0.016(3) 0.133(4) -0.014(3) C5T 0.254(6) 0.100(3) 0.094(3) -0.015(3) 0.033(4) 0.036(4) C6T 0.104(3) 0.100(3) 0.260(5) -0.084(3) 0.045(3) 0.003(3) C7T 0.186(5) 0.260(4) 0.373(6) -0.252(4) 0.130(4) -0.131(4) C8T 0.197(5) 0.128(4) 0.139(4) 0.004(3) 0.093(4) 0.005(4) C9T 0.547(9) 0.353(7) 0.150(4) -0.140(4) -0.204(5) 0.329(6) C10T 0.418(10) 0.047(3) 0.316(8) -0.003(4) 0.161(8) -0.010(5) N1T 0.134(3) 0.0899(19) 0.103(2) -0.0460(17) -0.004(2) 0.028(2) O1T 0.181(3) 0.1334(19) 0.143(2) -0.0856(17) -0.011(2) 0.057(2) O2T 0.0922(18) 0.1125(19) 0.165(2) -0.0639(17) 0.0271(17) -0.0022(16) C1M 0.180(6) 0.323(8) 0.479(11) -0.230(8) -0.099(7) 0.043(7) O1M 0.413(10) 0.383(7) 0.509(9) -0.299(6) -0.069(7) 0.059(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 C1 N1 1.318(3) . ? C1 N2 1.318(3) . ? C1 N3 1.330(3) . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? C2 N5 1.320(3) . ? C2 N6 1.325(3) . ? C2 N4 1.326(3) . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 H6A 0.8800 . ? N6 H6B 0.8800 . ? C3 N7 1.314(3) . ? C3 N9 1.322(3) . ? C3 N8 1.334(3) . ? N7 H7A 0.8800 . ? N7 H7B 0.8800 . ? N8 H8A 0.8800 . ? N8 H8B 0.8800 . ? N9 H9A 0.8800 . ? N9 H9B 0.8800 . ? C4 N11 1.306(3) . ? C4 N10 1.324(3) . ? C4 N12 1.329(3) . ? N10 H10A 0.8800 . ? N10 H10B 0.8800 . ? N11 H11A 0.8800 . ? N11 H11B 0.8800 . ? N12 H12A 0.8800 . ? N12 H12B 0.8800 . ? C5 C10 1.373(4) . ? C5 C6 1.377(3) . ? C5 S1 1.767(2) . ? C6 C7 1.379(3) . ? C6 H6 0.9500 . ? C7 C8 1.367(4) . ? C7 H7 0.9500 . ? C8 C9 1.365(4) . ? C8 N13 1.454(3) . ? C9 C10 1.388(4) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? N13 N13 1.222(4) 2_665 ? S1 O1 1.4493(16) . ? S1 O3 1.4531(16) . ? S1 O2 1.4555(17) . ? C11 C12 1.369(3) . ? C11 C16 1.381(3) . ? C11 S2 1.769(2) . ? C12 C13 1.396(4) . ? C12 H12 0.9500 . ? C13 C14 1.382(4) . ? C13 H13 0.9500 . ? C14 C15 1.370(3) . ? C14 N14 1.435(3) . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? N14 N14 1.232(4) 2_766 ? S2 O5 1.4543(15) . ? S2 O4 1.4558(16) . ? S2 O6 1.4587(16) . ? C17 C22 1.377(3) . ? C17 C18 1.383(3) . ? C17 S3 1.769(2) . ? C18 C19 1.373(3) . ? C18 H18 0.9500 . ? C19 C20 1.378(3) . ? C19 H19 0.9500 . ? C20 C21 1.369(4) . ? C20 N15 1.443(3) . ? C21 C22 1.391(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? N15 N15 1.241(4) 2_565 ? S3 O7 1.4543(16) . ? S3 O8 1.4544(16) . ? S3 O9 1.4589(16) . ? C23 C28 1.372(3) . ? C23 C24 1.374(4) . ? C23 S4 1.772(2) . ? C24 C25 1.390(4) . ? C24 H24 0.9500 . ? C25 C26 1.358(4) . ? C25 H25 0.9500 . ? C26 C27 1.365(4) . ? C26 N16 1.440(3) . ? C27 C28 1.377(3) . ? C27 H27 0.9500 . ? C28 H28 0.9500 . ? N16 N16 1.232(4) 2_666 ? S4 O10 1.4524(16) . ? S4 O11 1.4578(17) . ? S4 O12 1.4579(17) . ? C1T C8T 1.458(6) . ? C1T N1T 1.489(4) . ? C1T C2T 1.526(5) . ? C1T C7T 1.530(7) . ? C2T C3T 1.455(5) . ? C2T H2T1 0.9900 . ? C2T H2T2 0.9900 . ? C3T O2T 1.407(4) . ? C3T C4T 1.487(5) . ? C3T H3T 1.0000 . ? C4T C5T 1.530(7) . ? C4T H4T1 0.9900 . ? C4T H4T2 0.9900 . ? C5T C10T 1.420(7) . ? C5T N1T 1.523(5) . ? C5T C9T 1.525(9) . ? C6T O2T 1.361(5) . ? C6T H6T1 0.9800 . ? C6T H6T2 0.9800 . ? C6T H6T3 0.9800 . ? C7T H7T1 0.9800 . ? C7T H7T2 0.9800 . ? C7T H7T3 0.9800 . ? C8T H8T1 0.9800 . ? C8T H8T2 0.9800 . ? C8T H8T3 0.9800 . ? C9T H9T1 0.9800 . ? C9T H9T2 0.9800 . ? C9T H9T3 0.9800 . ? C10T H10C 0.9800 . ? C10T H10D 0.9800 . ? C10T H10E 0.9800 . ? N1T O1T 1.320(4) . ? C1M O1M 1.418(9) . ? C1M H1M1 0.9800 . ? C1M H1M2 0.9800 . ? C1M H1M3 0.9800 . ? O1M H1M 0.8400 . ? 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 N1 C1 N2 119.7(2) . . ? N1 C1 N3 120.5(2) . . ? N2 C1 N3 119.8(2) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? N5 C2 N6 120.4(2) . . ? N5 C2 N4 119.7(2) . . ? N6 C2 N4 119.9(2) . . ? C2 N4 H4A 120.0 . . ? C2 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C2 N5 H5A 120.0 . . ? C2 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C2 N6 H6A 120.0 . . ? C2 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? N7 C3 N9 120.7(2) . . ? N7 C3 N8 120.1(2) . . ? N9 C3 N8 119.2(2) . . ? C3 N7 H7A 120.0 . . ? C3 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? C3 N8 H8A 120.0 . . ? C3 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? C3 N9 H9A 120.0 . . ? C3 N9 H9B 120.0 . . ? H9A N9 H9B 120.0 . . ? N11 C4 N10 120.6(2) . . ? N11 C4 N12 119.6(2) . . ? N10 C4 N12 119.7(2) . . ? C4 N10 H10A 120.0 . . ? C4 N10 H10B 120.0 . . ? H10A N10 H10B 120.0 . . ? C4 N11 H11A 120.0 . . ? C4 N11 H11B 120.0 . . ? H11A N11 H11B 120.0 . . ? C4 N12 H12A 120.0 . . ? C4 N12 H12B 120.0 . . ? H12A N12 H12B 120.0 . . ? C10 C5 C6 119.7(2) . . ? C10 C5 S1 119.3(2) . . ? C6 C5 S1 121.0(2) . . ? C5 C6 C7 119.6(3) . . ? C5 C6 H6 120.2 . . ? C7 C6 H6 120.2 . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C9 C8 C7 120.3(2) . . ? C9 C8 N13 124.3(3) . . ? C7 C8 N13 115.3(2) . . ? C8 C9 C10 119.5(3) . . ? C8 C9 H9 120.2 . . ? C10 C9 H9 120.2 . . ? C5 C10 C9 120.3(3) . . ? C5 C10 H10 119.8 . . ? C9 C10 H10 119.8 . . ? N13 N13 C8 113.0(3) 2_665 . ? O1 S1 O3 112.31(10) . . ? O1 S1 O2 112.46(9) . . ? O3 S1 O2 112.43(10) . . ? O1 S1 C5 106.10(11) . . ? O3 S1 C5 106.67(10) . . ? O2 S1 C5 106.30(11) . . ? C12 C11 C16 120.1(2) . . ? C12 C11 S2 120.66(19) . . ? C16 C11 S2 119.24(16) . . ? C11 C12 C13 119.5(2) . . ? C11 C12 H12 120.3 . . ? C13 C12 H12 120.3 . . ? C14 C13 C12 120.0(2) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C15 C14 C13 120.3(2) . . ? C15 C14 N14 124.9(2) . . ? C13 C14 N14 114.8(2) . . ? C14 C15 C16 119.5(3) . . ? C14 C15 H15 120.2 . . ? C16 C15 H15 120.2 . . ? C11 C16 C15 120.6(2) . . ? C11 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? N14 N14 C14 113.0(2) 2_766 . ? O5 S2 O4 113.02(9) . . ? O5 S2 O6 111.71(9) . . ? O4 S2 O6 112.69(9) . . ? O5 S2 C11 106.35(10) . . ? O4 S2 C11 106.46(10) . . ? O6 S2 C11 105.98(10) . . ? C22 C17 C18 120.0(2) . . ? C22 C17 S3 120.48(19) . . ? C18 C17 S3 119.54(16) . . ? C19 C18 C17 120.4(2) . . ? C19 C18 H18 119.8 . . ? C17 C18 H18 119.8 . . ? C18 C19 C20 119.6(2) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? C21 C20 C19 120.5(2) . . ? C21 C20 N15 115.3(2) . . ? C19 C20 N15 124.1(2) . . ? C20 C21 C22 120.0(2) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C17 C22 C21 119.5(2) . . ? C17 C22 H22 120.3 . . ? C21 C22 H22 120.3 . . ? N15 N15 C20 113.0(2) 2_565 . ? O7 S3 O8 111.83(9) . . ? O7 S3 O9 113.19(10) . . ? O8 S3 O9 112.46(9) . . ? O7 S3 C17 106.30(10) . . ? O8 S3 C17 105.80(10) . . ? O9 S3 C17 106.64(10) . . ? C28 C23 C24 119.5(2) . . ? C28 C23 S4 121.59(19) . . ? C24 C23 S4 118.94(19) . . ? C23 C24 C25 120.2(3) . . ? C23 C24 H24 119.9 . . ? C25 C24 H24 119.9 . . ? C26 C25 C24 119.9(3) . . ? C26 C25 H25 120.1 . . ? C24 C25 H25 120.1 . . ? C25 C26 C27 119.9(2) . . ? C25 C26 N16 123.6(2) . . ? C27 C26 N16 116.5(2) . . ? C26 C27 C28 120.9(3) . . ? C26 C27 H27 119.6 . . ? C28 C27 H27 119.6 . . ? C23 C28 C27 119.7(3) . . ? C23 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? N16 N16 C26 113.7(3) 2_666 . ? O10 S4 O11 112.58(10) . . ? O10 S4 O12 112.80(10) . . ? O11 S4 O12 112.08(9) . . ? O10 S4 C23 106.35(10) . . ? O11 S4 C23 106.16(10) . . ? O12 S4 C23 106.24(10) . . ? C8T C1T N1T 107.2(4) . . ? C8T C1T C2T 111.8(4) . . ? N1T C1T C2T 107.8(3) . . ? C8T C1T C7T 110.5(4) . . ? N1T C1T C7T 107.1(3) . . ? C2T C1T C7T 112.1(4) . . ? C3T C2T C1T 117.5(3) . . ? C3T C2T H2T1 107.9 . . ? C1T C2T H2T1 107.9 . . ? C3T C2T H2T2 107.9 . . ? C1T C2T H2T2 107.9 . . ? H2T1 C2T H2T2 107.2 . . ? O2T C3T C2T 112.7(3) . . ? O2T C3T C4T 108.5(3) . . ? C2T C3T C4T 106.3(4) . . ? O2T C3T H3T 109.8 . . ? C2T C3T H3T 109.8 . . ? C4T C3T H3T 109.8 . . ? C3T C4T C5T 115.2(4) . . ? C3T C4T H4T1 108.5 . . ? C5T C4T H4T1 108.5 . . ? C3T C4T H4T2 108.5 . . ? C5T C4T H4T2 108.5 . . ? H4T1 C4T H4T2 107.5 . . ? C10T C5T N1T 106.0(4) . . ? C10T C5T C9T 108.7(5) . . ? N1T C5T C9T 105.7(5) . . ? C10T C5T C4T 113.3(6) . . ? N1T C5T C4T 104.8(3) . . ? C9T C5T C4T 117.4(5) . . ? O2T C6T H6T1 109.5 . . ? O2T C6T H6T2 109.5 . . ? H6T1 C6T H6T2 109.5 . . ? O2T C6T H6T3 109.5 . . ? H6T1 C6T H6T3 109.5 . . ? H6T2 C6T H6T3 109.5 . . ? C1T C7T H7T1 109.5 . . ? C1T C7T H7T2 109.5 . . ? H7T1 C7T H7T2 109.5 . . ? C1T C7T H7T3 109.5 . . ? H7T1 C7T H7T3 109.5 . . ? H7T2 C7T H7T3 109.5 . . ? C1T C8T H8T1 109.5 . . ? C1T C8T H8T2 109.5 . . ? H8T1 C8T H8T2 109.5 . . ? C1T C8T H8T3 109.5 . . ? H8T1 C8T H8T3 109.5 . . ? H8T2 C8T H8T3 109.5 . . ? C5T C9T H9T1 109.5 . . ? C5T C9T H9T2 109.5 . . ? H9T1 C9T H9T2 109.5 . . ? C5T C9T H9T3 109.5 . . ? H9T1 C9T H9T3 109.5 . . ? H9T2 C9T H9T3 109.5 . . ? C5T C10T H10C 109.5 . . ? C5T C10T H10D 109.5 . . ? H10C C10T H10D 109.5 . . ? C5T C10T H10E 109.5 . . ? H10C C10T H10E 109.5 . . ? H10D C10T H10E 109.5 . . ? O1T N1T C1T 115.4(3) . . ? O1T N1T C5T 115.9(3) . . ? C1T N1T C5T 124.8(3) . . ? C6T O2T C3T 115.5(3) . . ? O1M C1M H1M1 109.5 . . ? O1M C1M H1M2 109.5 . . ? H1M1 C1M H1M2 109.5 . . ? O1M C1M H1M3 109.5 . . ? H1M1 C1M H1M3 109.5 . . ? H1M2 C1M H1M3 109.5 . . ? C1M O1M H1M 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 C10 C5 C6 C7 0.7(4) . . . . ? S1 C5 C6 C7 -178.8(2) . . . . ? C5 C6 C7 C8 0.0(4) . . . . ? C6 C7 C8 C9 -0.4(5) . . . . ? C6 C7 C8 N13 178.2(3) . . . . ? C7 C8 C9 C10 0.1(5) . . . . ? N13 C8 C9 C10 -178.4(3) . . . . ? C6 C5 C10 C9 -1.0(4) . . . . ? S1 C5 C10 C9 178.5(2) . . . . ? C8 C9 C10 C5 0.6(5) . . . . ? C9 C8 N13 N13 3.4(5) . . . 2_665 ? C7 C8 N13 N13 -175.2(3) . . . 2_665 ? C10 C5 S1 O1 -49.8(2) . . . . ? C6 C5 S1 O1 129.7(2) . . . . ? C10 C5 S1 O3 70.1(2) . . . . ? C6 C5 S1 O3 -110.4(2) . . . . ? C10 C5 S1 O2 -169.7(2) . . . . ? C6 C5 S1 O2 9.7(2) . . . . ? C16 C11 C12 C13 -1.5(4) . . . . ? S2 C11 C12 C13 176.9(2) . . . . ? C11 C12 C13 C14 1.8(5) . . . . ? C12 C13 C14 C15 -1.5(4) . . . . ? C12 C13 C14 N14 179.4(3) . . . . ? C13 C14 C15 C16 0.8(4) . . . . ? N14 C14 C15 C16 179.7(3) . . . . ? C12 C11 C16 C15 0.7(4) . . . . ? S2 C11 C16 C15 -177.7(2) . . . . ? C14 C15 C16 C11 -0.4(4) . . . . ? C15 C14 N14 N14 -1.3(4) . . . 2_766 ? C13 C14 N14 N14 177.7(3) . . . 2_766 ? C12 C11 S2 O5 139.7(2) . . . . ? C16 C11 S2 O5 -41.9(2) . . . . ? C12 C11 S2 O4 18.9(2) . . . . ? C16 C11 S2 O4 -162.68(19) . . . . ? C12 C11 S2 O6 -101.3(2) . . . . ? C16 C11 S2 O6 77.1(2) . . . . ? C22 C17 C18 C19 1.1(4) . . . . ? S3 C17 C18 C19 -177.3(2) . . . . ? C17 C18 C19 C20 -0.8(4) . . . . ? C18 C19 C20 C21 0.1(4) . . . . ? C18 C19 C20 N15 -179.3(2) . . . . ? C19 C20 C21 C22 0.2(4) . . . . ? N15 C20 C21 C22 179.6(2) . . . . ? C18 C17 C22 C21 -0.8(4) . . . . ? S3 C17 C22 C21 177.6(2) . . . . ? C20 C21 C22 C17 0.1(4) . . . . ? C21 C20 N15 N15 172.2(3) . . . 2_565 ? C19 C20 N15 N15 -8.4(4) . . . 2_565 ? C22 C17 S3 O7 144.4(2) . . . . ? C18 C17 S3 O7 -37.2(2) . . . . ? C22 C17 S3 O8 -96.6(2) . . . . ? C18 C17 S3 O8 81.8(2) . . . . ? C22 C17 S3 O9 23.4(2) . . . . ? C18 C17 S3 O9 -158.27(19) . . . . ? C28 C23 C24 C25 1.7(4) . . . . ? S4 C23 C24 C25 -177.3(2) . . . . ? C23 C24 C25 C26 -0.3(5) . . . . ? C24 C25 C26 C27 -1.4(5) . . . . ? C24 C25 C26 N16 179.5(3) . . . . ? C25 C26 C27 C28 1.7(4) . . . . ? N16 C26 C27 C28 -179.2(3) . . . . ? C24 C23 C28 C27 -1.4(4) . . . . ? S4 C23 C28 C27 177.5(2) . . . . ? C26 C27 C28 C23 -0.3(4) . . . . ? C25 C26 N16 N16 -10.1(4) . . . 2_666 ? C27 C26 N16 N16 170.8(3) . . . 2_666 ? C28 C23 S4 O10 133.6(2) . . . . ? C24 C23 S4 O10 -47.5(2) . . . . ? C28 C23 S4 O11 -106.3(2) . . . . ? C24 C23 S4 O11 72.6(2) . . . . ? C28 C23 S4 O12 13.2(2) . . . . ? C24 C23 S4 O12 -167.9(2) . . . . ? C8T C1T C2T C3T 161.7(4) . . . . ? N1T C1T C2T C3T 44.1(5) . . . . ? C7T C1T C2T C3T -73.6(5) . . . . ? C1T C2T C3T O2T -177.9(4) . . . . ? C1T C2T C3T C4T -59.2(5) . . . . ? O2T C3T C4T C5T -174.0(4) . . . . ? C2T C3T C4T C5T 64.5(5) . . . . ? C3T C4T C5T C10T -167.8(5) . . . . ? C3T C4T C5T N1T -52.7(6) . . . . ? C3T C4T C5T C9T 64.2(6) . . . . ? C8T C1T N1T O1T 47.4(5) . . . . ? C2T C1T N1T O1T 168.0(4) . . . . ? C7T C1T N1T O1T -71.1(5) . . . . ? C8T C1T N1T C5T -155.6(4) . . . . ? C2T C1T N1T C5T -35.0(6) . . . . ? C7T C1T N1T C5T 85.9(5) . . . . ? C10T C5T N1T O1T -43.7(6) . . . . ? C9T C5T N1T O1T 71.5(5) . . . . ? C4T C5T N1T O1T -163.8(4) . . . . ? C10T C5T N1T C1T 159.3(5) . . . . ? C9T C5T N1T C1T -85.4(5) . . . . ? C4T C5T N1T C1T 39.3(6) . . . . ? C2T C3T O2T C6T -76.1(5) . . . . ? C4T C3T O2T C6T 166.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.536 _refine_diff_density_min -0.462 _refine_diff_density_rms 0.086 # Attachment '- GDS 7.cif' data_GDS_7 _database_code_depnum_ccdc_archive 'CCDC 802085' #TrackingRef '- GDS 7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H42 N7 O10 S2' _chemical_formula_weight 652.77 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 7.5142(4) _cell_length_b 24.1429(14) _cell_length_c 17.5439(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3182.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 9866 _cell_measurement_theta_min 2.78 _cell_measurement_theta_max 26.34 _exptl_crystal_description block _exptl_crystal_colour brown-yellow _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1388 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8840 _exptl_absorpt_correction_T_max 0.9642 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(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 APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 40607 _diffrn_reflns_av_R_equivalents 0.0255 _diffrn_reflns_av_sigmaI/netI 0.0168 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 26.48 _reflns_number_total 6573 _reflns_number_gt 6149 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0753P)^2^+0.5115P] 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(4) _refine_ls_number_reflns 6573 _refine_ls_number_parameters 426 _refine_ls_number_restraints 43 _refine_ls_R_factor_all 0.0417 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.1127 _refine_ls_wR_factor_gt 0.1096 _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_restrained_S_all 1.076 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.35856(15) 0.55686(5) 0.23756(8) 0.0387(3) Uani 1 1 d . . . C2 C 0.85048(16) 0.32634(5) 0.32471(9) 0.0471(4) Uani 1 1 d . . . C3 C 1.08854(15) 0.31545(4) 0.81607(7) 0.0309(3) Uani 1 1 d . . . C4 C 1.10561(16) 0.25763(5) 0.81384(7) 0.0367(3) Uani 1 1 d . . . H4 H 1.1411 0.2396 0.7682 0.044 Uiso 1 1 calc R . . C5 C 1.07048(17) 0.22747(5) 0.87832(7) 0.0367(3) Uani 1 1 d . . . H5 H 1.0822 0.1883 0.8768 0.044 Uiso 1 1 calc R . . C6 C 1.01788(14) 0.25292(5) 0.94612(7) 0.0320(3) Uani 1 1 d . . . C7 C 0.99931(17) 0.31023(5) 0.94660(7) 0.0372(3) Uani 1 1 d . . . H7 H 0.9623 0.3283 0.9920 0.045 Uiso 1 1 calc R . . C8 C 1.03392(17) 0.34138(5) 0.88188(7) 0.0362(3) Uani 1 1 d . . . H8 H 1.0200 0.3805 0.8830 0.043 Uiso 1 1 calc R . . C9 C 0.90532(15) 0.16209(5) 1.15002(7) 0.0318(3) Uani 1 1 d . . . C10 C 0.86490(15) 0.13905(5) 1.08011(8) 0.0347(3) Uani 1 1 d . . . H10 H 0.8098 0.1037 1.0774 0.042 Uiso 1 1 calc R . . C11 C 0.90523(16) 0.16785(5) 1.01388(7) 0.0343(3) Uani 1 1 d . . . H11 H 0.8797 0.1516 0.9658 0.041 Uiso 1 1 calc R . . C12 C 0.98280(15) 0.22035(5) 1.01688(7) 0.0329(3) Uani 1 1 d . . . C13 C 1.02378(17) 0.24267(5) 1.08800(7) 0.0398(3) Uani 1 1 d . . . H13 H 1.0788 0.2780 1.0910 0.048 Uiso 1 1 calc R . . C14 C 0.98539(17) 0.21403(5) 1.15449(7) 0.0387(3) Uani 1 1 d . . . H14 H 1.0134 0.2297 1.2027 0.046 Uiso 1 1 calc R . . C1T C 0.6902(2) -0.02002(6) 0.53187(8) 0.0489(4) Uani 1 1 d . . . C2T C 0.7530(2) 0.03676(7) 0.55687(9) 0.0579(4) Uani 1 1 d . . . H2T1 H 0.6839 0.0484 0.6022 0.069 Uiso 1 1 calc R . . H2T2 H 0.8797 0.0344 0.5720 0.069 Uiso 1 1 calc R . . C3T C 0.7337(3) 0.07970(7) 0.49622(11) 0.0678(5) Uani 1 1 d . . . C4T C 0.5791(3) 0.07334(8) 0.44260(12) 0.0843(6) Uani 1 1 d . . . H4T1 H 0.6243 0.0585 0.3937 0.101 Uiso 1 1 calc R . . H4T2 H 0.5293 0.1105 0.4322 0.101 Uiso 1 1 calc R . . C5T C 0.4287(2) 0.03598(6) 0.47020(9) 0.0490(4) Uani 1 1 d . . . C6T C 0.3132(3) 0.06232(10) 0.53009(15) 0.0952(7) Uani 1 1 d . . . H6T1 H 0.2320 0.0345 0.5512 0.143 Uiso 1 1 calc R . . H6T2 H 0.2441 0.0925 0.5072 0.143 Uiso 1 1 calc R . . H6T3 H 0.3883 0.0772 0.5709 0.143 Uiso 1 1 calc R . . C7T C 0.3128(3) 0.02049(9) 0.40047(11) 0.0768(6) Uani 1 1 d . . . H7T1 H 0.3863 0.0013 0.3626 0.115 Uiso 1 1 calc R . . H7T2 H 0.2631 0.0542 0.3779 0.115 Uiso 1 1 calc R . . H7T3 H 0.2157 -0.0039 0.4168 0.115 Uiso 1 1 calc R . . C8T C 0.8093(2) -0.04412(8) 0.46913(11) 0.0662(5) Uani 1 1 d . . . H8T1 H 0.7594 -0.0793 0.4514 0.099 Uiso 1 1 calc R . . H8T2 H 0.9291 -0.0504 0.4895 0.099 Uiso 1 1 calc R . . H8T3 H 0.8156 -0.0180 0.4264 0.099 Uiso 1 1 calc R . . C9T C 0.6883(3) -0.05864(8) 0.60055(10) 0.0715(5) Uani 1 1 d . . . H9T1 H 0.6041 -0.0446 0.6386 0.107 Uiso 1 1 calc R . . H9T2 H 0.8077 -0.0604 0.6229 0.107 Uiso 1 1 calc R . . H9T3 H 0.6519 -0.0958 0.5843 0.107 Uiso 1 1 calc R . . N1 N 0.35694(14) 0.61142(4) 0.23230(10) 0.0489(3) Uani 1 1 d . . . H1A H 0.2550 0.6292 0.2292 0.059 Uiso 1 1 calc R . . H1B H 0.4578 0.6300 0.2319 0.059 Uiso 1 1 calc R . . N2 N 0.51240(15) 0.53026(4) 0.24515(8) 0.0479(3) Uani 1 1 d . . . H2A H 0.6128 0.5490 0.2467 0.057 Uiso 1 1 calc R . . H2B H 0.5139 0.4939 0.2487 0.057 Uiso 1 1 calc R . . N3 N 0.20768(14) 0.52869(4) 0.23815(8) 0.0461(3) Uani 1 1 d . . . H3A H 0.1054 0.5463 0.2350 0.055 Uiso 1 1 calc R . . H3B H 0.2095 0.4923 0.2417 0.055 Uiso 1 1 calc R . . N4 N 0.69902(17) 0.31693(5) 0.36192(9) 0.0567(4) Uani 1 1 d . . . H4A H 0.5997 0.3326 0.3464 0.068 Uiso 1 1 calc R . . H4B H 0.6983 0.2951 0.4020 0.068 Uiso 1 1 calc R . . N5 N 0.85540(16) 0.35851(5) 0.26520(8) 0.0500(3) Uani 1 1 d . . . H5A H 0.7574 0.3745 0.2488 0.060 Uiso 1 1 calc R . . H5B H 0.9567 0.3642 0.2413 0.060 Uiso 1 1 calc R . . N6 N 0.99792(17) 0.30183(5) 0.35122(9) 0.0563(4) Uani 1 1 d . . . H6A H 1.1006 0.3073 0.3283 0.068 Uiso 1 1 calc R . . H6B H 0.9921 0.2802 0.3915 0.068 Uiso 1 1 calc R . . N1T N 0.50753(15) -0.01505(4) 0.50121(6) 0.0437(3) Uani 1 1 d . . . O1 O 0.98568(12) 0.34415(4) 0.68109(5) 0.0451(2) Uani 1 1 d . . . O2 O 1.14011(12) 0.41259(4) 0.75578(6) 0.0422(2) Uani 1 1 d . . . O3 O 1.30343(13) 0.33489(4) 0.70371(6) 0.0450(2) Uani 1 1 d . . . O4 O 0.69692(12) 0.09309(3) 1.22119(6) 0.0431(2) Uani 1 1 d . . . O5 O 0.84008(13) 0.16621(4) 1.29457(6) 0.0457(2) Uani 1 1 d . . . O6 O 1.01291(11) 0.08896(4) 1.24814(6) 0.0436(2) Uani 1 1 d . . . O1T O 0.41309(17) -0.05902(4) 0.50128(7) 0.0635(3) Uani 1 1 d . . . O2T O 0.8406(2) 0.11611(6) 0.48723(11) 0.0978(5) Uani 1 1 d . . . S1 S 1.13386(4) 0.354469(11) 0.732829(19) 0.03438(6) Uani 1 1 d . . . S2 S 0.85928(4) 0.125083(11) 1.23465(2) 0.03589(7) Uani 1 1 d . . . O7 O 1.3093(4) 0.24100(10) 0.60941(15) 0.0709(7) Uani 0.504(2) 1 d PU A -1 H7O H 1.3829 0.2253 0.6382 0.106 Uiso 0.504(2) 1 calc PR A -1 C15 C 1.2536(11) 0.2016(3) 0.5473(4) 0.130(2) Uani 0.504(2) 1 d PU A -1 H15A H 1.1723 0.1737 0.5683 0.195 Uiso 0.504(2) 1 calc PR A -1 H15B H 1.3590 0.1831 0.5263 0.195 Uiso 0.504(2) 1 calc PR A -1 H15C H 1.1931 0.2222 0.5067 0.195 Uiso 0.504(2) 1 calc PR A -1 O7' O 0.8556(3) 0.23022(7) 0.45770(11) 0.0562(7) Uani 0.496(2) 1 d PU A -2 H7O' H 0.8750 0.2535 0.4232 0.084 Uiso 0.496(2) 1 calc PR A -2 C15' C 1.0408(8) 0.2160(3) 0.5013(4) 0.122(2) Uani 0.496(2) 1 d PU A -2 H15D H 1.1152 0.2492 0.5034 0.184 Uiso 0.496(2) 1 calc PR A -2 H15E H 1.1039 0.1867 0.4735 0.184 Uiso 0.496(2) 1 calc PR A -2 H15F H 1.0149 0.2033 0.5532 0.184 Uiso 0.496(2) 1 calc PR A -2 O8 O 0.8577(11) 0.2261(4) 0.4653(4) 0.297(4) Uani 0.685(3) 1 d PU B -1 H8O H 0.7695 0.2325 0.4382 0.446 Uiso 0.685(3) 1 d PR B -1 H9O H 0.8629 0.1941 0.4744 0.446 Uiso 0.685(3) 1 d PR B -1 O8' O 1.4451(6) 0.25666(15) 0.6080(2) 0.0668(11) Uani 0.315(3) 1 d PU B -2 H8O' H 1.3586 0.2769 0.6342 0.100 Uiso 0.315(3) 1 d PR B -2 H9O' H 1.4800 0.2262 0.6326 0.100 Uiso 0.315(3) 1 d PRU B -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 C1 0.0375(5) 0.0377(5) 0.0410(5) -0.0070(6) 0.0017(5) 0.0014(5) C2 0.0302(5) 0.0296(5) 0.0815(9) -0.0196(6) -0.0062(6) -0.0044(5) C3 0.0270(5) 0.0279(5) 0.0380(5) 0.0032(4) -0.0043(4) -0.0008(4) C4 0.0384(6) 0.0310(5) 0.0406(6) -0.0021(5) -0.0031(5) 0.0044(5) C5 0.0376(6) 0.0267(5) 0.0456(6) 0.0003(5) -0.0029(5) 0.0031(5) C6 0.0254(5) 0.0305(5) 0.0402(5) 0.0012(5) -0.0073(4) -0.0020(4) C7 0.0394(6) 0.0341(6) 0.0381(6) -0.0042(5) -0.0026(5) 0.0005(5) C8 0.0382(6) 0.0255(5) 0.0447(6) -0.0013(5) -0.0043(5) 0.0013(5) C9 0.0275(5) 0.0285(5) 0.0393(5) 0.0047(4) -0.0015(4) 0.0000(4) C10 0.0336(6) 0.0255(5) 0.0448(6) -0.0010(5) -0.0030(5) -0.0020(4) C11 0.0326(5) 0.0310(5) 0.0392(5) -0.0032(5) -0.0053(5) -0.0002(5) C12 0.0279(5) 0.0306(5) 0.0401(6) 0.0008(5) -0.0020(5) -0.0002(4) C13 0.0438(6) 0.0341(6) 0.0414(6) 0.0032(5) -0.0107(5) -0.0132(5) C14 0.0421(6) 0.0368(6) 0.0373(6) 0.0016(5) -0.0074(5) -0.0095(5) C1T 0.0487(7) 0.0552(7) 0.0429(7) 0.0090(6) -0.0024(6) 0.0037(7) C2T 0.0574(8) 0.0662(9) 0.0501(8) 0.0012(7) -0.0108(7) -0.0081(7) C3T 0.0755(10) 0.0551(8) 0.0728(10) 0.0107(8) -0.0120(9) -0.0264(8) C4T 0.1078(13) 0.0661(10) 0.0789(10) 0.0339(8) -0.0299(11) -0.0285(10) C5T 0.0549(7) 0.0414(7) 0.0506(7) 0.0060(6) -0.0123(6) -0.0032(6) C6T 0.0963(13) 0.0959(13) 0.0935(14) -0.0304(11) -0.0188(12) 0.0384(12) C7T 0.0962(12) 0.0703(10) 0.0639(9) 0.0070(9) -0.0313(9) -0.0023(10) C8T 0.0562(8) 0.0740(10) 0.0684(10) -0.0030(9) 0.0006(8) 0.0095(8) C9T 0.0871(11) 0.0716(10) 0.0559(9) 0.0232(8) -0.0074(9) 0.0081(9) N1 0.0376(5) 0.0341(5) 0.0749(7) -0.0048(6) -0.0031(6) 0.0003(4) N2 0.0369(5) 0.0368(5) 0.0700(8) -0.0040(5) 0.0007(5) 0.0013(4) N3 0.0378(5) 0.0330(5) 0.0675(7) -0.0044(5) 0.0012(6) 0.0018(4) N4 0.0372(6) 0.0491(6) 0.0838(9) 0.0146(6) -0.0043(6) -0.0066(5) N5 0.0363(5) 0.0568(7) 0.0569(7) 0.0012(6) -0.0013(5) 0.0022(5) N6 0.0387(6) 0.0380(6) 0.0923(10) 0.0054(6) -0.0065(6) 0.0018(5) N1T 0.0456(6) 0.0422(6) 0.0435(6) 0.0063(5) -0.0007(5) -0.0051(5) O1 0.0470(5) 0.0469(5) 0.0414(4) 0.0033(4) -0.0083(4) 0.0039(4) O2 0.0433(4) 0.0299(4) 0.0535(5) 0.0023(4) 0.0053(4) -0.0004(3) O3 0.0418(4) 0.0390(4) 0.0542(5) 0.0020(4) 0.0095(4) 0.0013(4) O4 0.0346(4) 0.0372(4) 0.0575(5) 0.0043(4) 0.0048(4) -0.0066(3) O5 0.0485(5) 0.0453(5) 0.0433(5) -0.0013(4) 0.0052(4) -0.0054(4) O6 0.0377(4) 0.0386(4) 0.0546(5) 0.0103(4) -0.0041(4) 0.0001(4) O1T 0.0728(7) 0.0453(5) 0.0724(7) 0.0117(5) 0.0019(6) -0.0180(5) O2T 0.1110(11) 0.0756(8) 0.1069(11) 0.0249(8) -0.0193(9) -0.0491(7) S1 0.03352(12) 0.03003(12) 0.03958(13) 0.00348(12) 0.00010(12) 0.00160(10) S2 0.03308(12) 0.03247(12) 0.04212(13) 0.00482(14) 0.00177(13) -0.00338(10) O7 0.0861(16) 0.0597(13) 0.0670(13) -0.0051(11) -0.0153(13) 0.0162(12) C15 0.158(5) 0.131(4) 0.102(4) 0.012(4) 0.004(4) 0.035(4) O7' 0.1099(18) 0.0274(8) 0.0312(8) 0.0093(7) -0.0051(10) -0.0221(9) C15' 0.119(4) 0.145(4) 0.103(4) 0.016(3) 0.003(3) -0.053(3) O8 0.277(8) 0.407(10) 0.207(7) 0.078(7) -0.027(6) -0.049(6) O8' 0.096(3) 0.0533(19) 0.0509(18) 0.0096(15) 0.008(2) 0.0249(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 C1 N1 1.3207(16) . ? C1 N3 1.3221(16) . ? C1 N2 1.3290(16) . ? C2 N5 1.302(2) . ? C2 N4 1.3316(19) . ? C2 N6 1.3394(18) . ? C3 C8 1.3760(17) . ? C3 C4 1.4023(16) . ? C3 S1 1.7709(12) . ? C4 C5 1.3710(18) . ? C4 H4 0.9500 . ? C5 C6 1.3959(17) . ? C5 H5 0.9500 . ? C6 C7 1.3905(17) . ? C6 C12 1.4932(17) . ? C7 C8 1.3865(18) . ? C7 H7 0.9500 . ? C8 H8 0.9500 . ? C9 C10 1.3806(18) . ? C9 C14 1.3929(16) . ? C9 S2 1.7672(12) . ? C10 C11 1.3877(18) . ? C10 H10 0.9500 . ? C11 C12 1.3959(16) . ? C11 H11 0.9500 . ? C12 C13 1.3935(17) . ? C13 C14 1.3864(18) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C1T N1T 1.4794(19) . ? C1T C2T 1.515(2) . ? C1T C9T 1.524(2) . ? C1T C8T 1.533(2) . ? C2T C3T 1.493(2) . ? C2T H2T1 0.9900 . ? C2T H2T2 0.9900 . ? C3T O2T 1.201(2) . ? C3T C4T 1.502(3) . ? C4T C5T 1.525(3) . ? C4T H4T1 0.9900 . ? C4T H4T2 0.9900 . ? C5T N1T 1.4713(18) . ? C5T C6T 1.504(3) . ? C5T C7T 1.548(2) . ? C6T H6T1 0.9800 . ? C6T H6T2 0.9800 . ? C6T H6T3 0.9800 . ? C7T H7T1 0.9800 . ? C7T H7T2 0.9800 . ? C7T H7T3 0.9800 . ? C8T H8T1 0.9800 . ? C8T H8T2 0.9800 . ? C8T H8T3 0.9800 . ? C9T H9T1 0.9800 . ? C9T H9T2 0.9800 . ? C9T H9T3 0.9800 . ? N1 H1A 0.8800 . ? N1 H1B 0.8800 . ? N2 H2A 0.8800 . ? N2 H2B 0.8800 . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? N6 H6A 0.8800 . ? N6 H6B 0.8800 . ? N1T O1T 1.2770(15) . ? O1 S1 1.4580(10) . ? O2 S1 1.4605(9) . ? O3 S1 1.4519(10) . ? O4 S2 1.4631(9) . ? O5 S2 1.4532(10) . ? O6 S2 1.4660(9) . ? O7 C15 1.507(7) . ? O7 H7O 0.8400 . ? O7 H8O' 1.0373 . ? O7 H9O' 1.3919 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? O7' C15' 1.624(7) . ? O7' H7O' 0.8400 . ? O7' H8O 0.7343 . ? O7' H9O 0.9219 . ? C15' H15D 0.9800 . ? C15' H15E 0.9800 . ? C15' H15F 0.9800 . ? C15' H9O 1.5128 . ? O8 H8O 0.8307 . ? O8 H9O 0.7908 . ? O8' H8O' 0.9335 . ? O8' H9O' 0.8921 . ? 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 N1 C1 N3 120.38(11) . . ? N1 C1 N2 119.80(11) . . ? N3 C1 N2 119.77(11) . . ? N5 C2 N4 121.29(13) . . ? N5 C2 N6 121.24(13) . . ? N4 C2 N6 117.47(14) . . ? C8 C3 C4 120.23(11) . . ? C8 C3 S1 120.49(8) . . ? C4 C3 S1 119.27(9) . . ? C5 C4 C3 119.22(11) . . ? C5 C4 H4 120.4 . . ? C3 C4 H4 120.4 . . ? C4 C5 C6 121.59(11) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C7 C6 C5 118.14(11) . . ? C7 C6 C12 120.08(11) . . ? C5 C6 C12 121.78(10) . . ? C8 C7 C6 121.05(11) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C3 C8 C7 119.76(11) . . ? C3 C8 H8 120.1 . . ? C7 C8 H8 120.1 . . ? C10 C9 C14 120.52(11) . . ? C10 C9 S2 119.97(9) . . ? C14 C9 S2 119.50(9) . . ? C9 C10 C11 119.60(11) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C10 C11 C12 120.97(11) . . ? C10 C11 H11 119.5 . . ? C12 C11 H11 119.5 . . ? C13 C12 C11 118.50(11) . . ? C13 C12 C6 120.12(10) . . ? C11 C12 C6 121.37(11) . . ? C14 C13 C12 120.96(11) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C9 119.43(11) . . ? C13 C14 H14 120.3 . . ? C9 C14 H14 120.3 . . ? N1T C1T C2T 108.72(12) . . ? N1T C1T C9T 109.16(13) . . ? C2T C1T C9T 109.14(13) . . ? N1T C1T C8T 108.15(12) . . ? C2T C1T C8T 111.69(14) . . ? C9T C1T C8T 109.94(14) . . ? C3T C2T C1T 113.06(14) . . ? C3T C2T H2T1 109.0 . . ? C1T C2T H2T1 109.0 . . ? C3T C2T H2T2 109.0 . . ? C1T C2T H2T2 109.0 . . ? H2T1 C2T H2T2 107.8 . . ? O2T C3T C2T 122.44(18) . . ? O2T C3T C4T 120.64(18) . . ? C2T C3T C4T 116.79(15) . . ? C3T C4T C5T 115.75(16) . . ? C3T C4T H4T1 108.3 . . ? C5T C4T H4T1 108.3 . . ? C3T C4T H4T2 108.3 . . ? C5T C4T H4T2 108.3 . . ? H4T1 C4T H4T2 107.4 . . ? N1T C5T C6T 109.15(14) . . ? N1T C5T C4T 108.33(13) . . ? C6T C5T C4T 113.55(16) . . ? N1T C5T C7T 108.44(12) . . ? C6T C5T C7T 109.25(16) . . ? C4T C5T C7T 108.00(15) . . ? C5T C6T H6T1 109.5 . . ? C5T C6T H6T2 109.5 . . ? H6T1 C6T H6T2 109.5 . . ? C5T C6T H6T3 109.5 . . ? H6T1 C6T H6T3 109.5 . . ? H6T2 C6T H6T3 109.5 . . ? C5T C7T H7T1 109.5 . . ? C5T C7T H7T2 109.5 . . ? H7T1 C7T H7T2 109.5 . . ? C5T C7T H7T3 109.5 . . ? H7T1 C7T H7T3 109.5 . . ? H7T2 C7T H7T3 109.5 . . ? C1T C8T H8T1 109.5 . . ? C1T C8T H8T2 109.5 . . ? H8T1 C8T H8T2 109.5 . . ? C1T C8T H8T3 109.5 . . ? H8T1 C8T H8T3 109.5 . . ? H8T2 C8T H8T3 109.5 . . ? C1T C9T H9T1 109.5 . . ? C1T C9T H9T2 109.5 . . ? H9T1 C9T H9T2 109.5 . . ? C1T C9T H9T3 109.5 . . ? H9T1 C9T H9T3 109.5 . . ? H9T2 C9T H9T3 109.5 . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C1 N2 H2A 120.0 . . ? C1 N2 H2B 120.0 . . ? H2A N2 H2B 120.0 . . ? C1 N3 H3A 120.0 . . ? C1 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C2 N4 H4A 120.0 . . ? C2 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C2 N5 H5A 120.0 . . ? C2 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? C2 N6 H6A 120.0 . . ? C2 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? O1T N1T C5T 118.22(12) . . ? O1T N1T C1T 116.62(11) . . ? C5T N1T C1T 125.16(11) . . ? O3 S1 O1 113.30(6) . . ? O3 S1 O2 112.44(5) . . ? O1 S1 O2 111.12(6) . . ? O3 S1 C3 106.61(6) . . ? O1 S1 C3 106.00(6) . . ? O2 S1 C3 106.85(5) . . ? O5 S2 O4 113.25(6) . . ? O5 S2 O6 111.59(6) . . ? O4 S2 O6 111.63(5) . . ? O5 S2 C9 106.36(6) . . ? O4 S2 C9 107.13(6) . . ? O6 S2 C9 106.39(6) . . ? C15 O7 H8O' 158.5 . . ? H7O O7 H8O' 83.7 . . ? C15 O7 H9O' 107.8 . . ? H7O O7 H9O' 26.1 . . ? H8O' O7 H9O' 76.3 . . ? C15' O7' H7O' 109.5 . . ? C15' O7' H8O 172.0 . . ? H7O' O7' H8O 76.5 . . ? C15' O7' H9O 66.4 . . ? H7O' O7' H9O 148.6 . . ? H8O O7' H9O 105.7 . . ? O7' C15' H15D 109.5 . . ? O7' C15' H15E 109.5 . . ? H15D C15' H15E 109.5 . . ? O7' C15' H15F 109.5 . . ? H15D C15' H15F 109.5 . . ? H15E C15' H15F 109.5 . . ? O7' C15' H9O 33.9 . . ? H15D C15' H9O 143.4 . . ? H15E C15' H9O 91.2 . . ? H15F C15' H9O 90.3 . . ? H8O O8 H9O 109.6 . . ? H8O' O8' H9O' 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 C8 C3 C4 C5 -1.21(18) . . . . ? S1 C3 C4 C5 180.00(10) . . . . ? C3 C4 C5 C6 0.09(19) . . . . ? C4 C5 C6 C7 0.85(18) . . . . ? C4 C5 C6 C12 -178.82(11) . . . . ? C5 C6 C7 C8 -0.72(18) . . . . ? C12 C6 C7 C8 178.97(11) . . . . ? C4 C3 C8 C7 1.35(18) . . . . ? S1 C3 C8 C7 -179.88(9) . . . . ? C6 C7 C8 C3 -0.37(19) . . . . ? C14 C9 C10 C11 0.28(17) . . . . ? S2 C9 C10 C11 -178.53(9) . . . . ? C9 C10 C11 C12 -1.34(17) . . . . ? C10 C11 C12 C13 1.82(17) . . . . ? C10 C11 C12 C6 -176.72(11) . . . . ? C7 C6 C12 C13 -34.13(16) . . . . ? C5 C6 C12 C13 145.54(12) . . . . ? C7 C6 C12 C11 144.39(12) . . . . ? C5 C6 C12 C11 -35.94(16) . . . . ? C11 C12 C13 C14 -1.28(18) . . . . ? C6 C12 C13 C14 177.29(11) . . . . ? C12 C13 C14 C9 0.26(19) . . . . ? C10 C9 C14 C13 0.25(18) . . . . ? S2 C9 C14 C13 179.07(10) . . . . ? N1T C1T C2T C3T -52.40(18) . . . . ? C9T C1T C2T C3T -171.38(15) . . . . ? C8T C1T C2T C3T 66.86(19) . . . . ? C1T C2T C3T O2T -143.27(19) . . . . ? C1T C2T C3T C4T 32.7(2) . . . . ? O2T C3T C4T C5T -165.07(19) . . . . ? C2T C3T C4T C5T 18.9(3) . . . . ? C3T C4T C5T N1T -46.0(2) . . . . ? C3T C4T C5T C6T 75.4(2) . . . . ? C3T C4T C5T C7T -163.28(17) . . . . ? C6T C5T N1T O1T 81.36(17) . . . . ? C4T C5T N1T O1T -154.55(14) . . . . ? C7T C5T N1T O1T -37.58(18) . . . . ? C6T C5T N1T C1T -99.46(17) . . . . ? C4T C5T N1T C1T 24.63(19) . . . . ? C7T C5T N1T C1T 141.60(14) . . . . ? C2T C1T N1T O1T -157.35(12) . . . . ? C9T C1T N1T O1T -38.38(17) . . . . ? C8T C1T N1T O1T 81.20(16) . . . . ? C2T C1T N1T C5T 23.46(18) . . . . ? C9T C1T N1T C5T 142.42(14) . . . . ? C8T C1T N1T C5T -97.99(16) . . . . ? C8 C3 S1 O3 132.71(10) . . . . ? C4 C3 S1 O3 -48.50(11) . . . . ? C8 C3 S1 O1 -106.30(10) . . . . ? C4 C3 S1 O1 72.48(10) . . . . ? C8 C3 S1 O2 12.28(11) . . . . ? C4 C3 S1 O2 -168.93(9) . . . . ? C10 C9 S2 O5 -155.34(9) . . . . ? C14 C9 S2 O5 25.83(11) . . . . ? C10 C9 S2 O4 -33.94(11) . . . . ? C14 C9 S2 O4 147.23(10) . . . . ? C10 C9 S2 O6 85.58(10) . . . . ? C14 C9 S2 O6 -93.25(10) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.48 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.411 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.053 # Attachment '- GDS 8.cif' data_GDS_8 _database_code_depnum_ccdc_archive 'CCDC 802086' #TrackingRef '- GDS 8.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H38 N9 O9 S2' _chemical_formula_weight 648.74 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 Pna2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 7.2608(3) _cell_length_b 23.5817(11) _cell_length_c 18.4741(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3163.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9990 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 29.00 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.362 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1372 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9468 _exptl_absorpt_correction_T_max 0.9707 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 57690 _diffrn_reflns_av_R_equivalents 0.0413 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -33 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.40 _diffrn_reflns_theta_max 30.56 _reflns_number_total 8388 _reflns_number_gt 7477 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.3720P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(4) _refine_ls_number_reflns 8388 _refine_ls_number_parameters 394 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0464 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0920 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _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 S1 S 0.28424(5) 0.625624(18) 0.19254(2) 0.01821(9) Uani 1 1 d . . . S2 S 0.68920(5) 0.850928(18) 0.78376(3) 0.01822(9) Uani 1 1 d . . . O1 O 0.26671(18) 0.66747(6) 0.13498(8) 0.0244(3) Uani 1 1 d . . . O2 O 0.11376(16) 0.59500(5) 0.20742(7) 0.0223(3) Uani 1 1 d . . . O3 O 0.43843(17) 0.58677(5) 0.18004(7) 0.0228(3) Uani 1 1 d . . . O4 O 0.69911(17) 0.91124(5) 0.76503(8) 0.0230(3) Uani 1 1 d . . . O5 O 0.86338(18) 0.82903(5) 0.81045(7) 0.0225(3) Uani 1 1 d . . . O6 O 0.53474(18) 0.83874(5) 0.83203(8) 0.0234(3) Uani 1 1 d . . . N1 N 0.4826(2) 0.75314(7) 0.45858(9) 0.0237(3) Uani 1 1 d . . . N2 N 0.5102(2) 0.72396(6) 0.51428(9) 0.0213(3) Uani 1 1 d . . . C1 C 0.3383(2) 0.66351(8) 0.27189(10) 0.0173(3) Uani 1 1 d . . . C2 C 0.3072(2) 0.63843(8) 0.33884(11) 0.0199(3) Uani 1 1 d . . . H2 H 0.2537 0.6017 0.3414 0.024 Uiso 1 1 calc R . . C3 C 0.3538(3) 0.66678(8) 0.40158(11) 0.0214(4) Uani 1 1 d . . . H3 H 0.3324 0.6498 0.4474 0.026 Uiso 1 1 calc R . . C4 C 0.4324(2) 0.72051(8) 0.39702(10) 0.0203(4) Uani 1 1 d . . . C5 C 0.4585(3) 0.74632(8) 0.32986(11) 0.0255(4) Uani 1 1 d . . . H5 H 0.5073 0.7836 0.3272 0.031 Uiso 1 1 calc R . . C6 C 0.4130(3) 0.71740(8) 0.26697(11) 0.0236(4) Uani 1 1 d . . . H6 H 0.4330 0.7344 0.2210 0.028 Uiso 1 1 calc R . . C7 C 0.5571(2) 0.75721(8) 0.57673(10) 0.0199(3) Uani 1 1 d . . . C8 C 0.5702(3) 0.81630(8) 0.57551(11) 0.0256(4) Uani 1 1 d . . . H8 H 0.5496 0.8366 0.5319 0.031 Uiso 1 1 calc R . . C9 C 0.6134(3) 0.84469(8) 0.63836(11) 0.0240(4) Uani 1 1 d . . . H9 H 0.6240 0.8848 0.6381 0.029 Uiso 1 1 calc R . . C10 C 0.6415(2) 0.81478(7) 0.70232(10) 0.0184(3) Uani 1 1 d . . . C11 C 0.6315(2) 0.75571(7) 0.70341(10) 0.0206(4) Uani 1 1 d . . . H11 H 0.6543 0.7353 0.7468 0.025 Uiso 1 1 calc R . . C12 C 0.5876(2) 0.72741(7) 0.64007(10) 0.0208(4) Uani 1 1 d . . . H12 H 0.5784 0.6872 0.6401 0.025 Uiso 1 1 calc R . . C13 C 0.3030(2) 0.44709(8) 0.25455(11) 0.0226(4) Uani 1 1 d . . . N3 N 0.1439(2) 0.47361(7) 0.24372(10) 0.0269(4) Uani 1 1 d . . . H3A H 0.0395 0.4563 0.2535 0.032 Uiso 1 1 calc R . . H3B H 0.1430 0.5085 0.2267 0.032 Uiso 1 1 calc R . . N4 N 0.4603(2) 0.47338(7) 0.23976(11) 0.0287(4) Uani 1 1 d . . . H4A H 0.5659 0.4559 0.2469 0.034 Uiso 1 1 calc R . . H4B H 0.4590 0.5082 0.2228 0.034 Uiso 1 1 calc R . . N5 N 0.3050(2) 0.39461(7) 0.28010(11) 0.0265(3) Uani 1 1 d . . . H5A H 0.4106 0.3772 0.2873 0.032 Uiso 1 1 calc R . . H5B H 0.2007 0.3772 0.2899 0.032 Uiso 1 1 calc R . . C14 C 0.2771(2) 0.82566(8) 0.08354(11) 0.0202(4) Uani 1 1 d . . . N6 N 0.1211(2) 0.82004(7) 0.04728(9) 0.0244(3) Uani 1 1 d . . . H6A H 0.1201 0.8024 0.0053 0.029 Uiso 1 1 calc R . . H6B H 0.0182 0.8340 0.0651 0.029 Uiso 1 1 calc R . . N7 N 0.2780(2) 0.85202(7) 0.14715(10) 0.0244(3) Uani 1 1 d . . . H7A H 0.3815 0.8556 0.1715 0.029 Uiso 1 1 calc R . . H7B H 0.1750 0.8659 0.1649 0.029 Uiso 1 1 calc R . . N8 N 0.4315(2) 0.80481(7) 0.05690(9) 0.0240(3) Uani 1 1 d . . . H8A H 0.4307 0.7871 0.0150 0.029 Uiso 1 1 calc R . . H8B H 0.5352 0.8086 0.0811 0.029 Uiso 1 1 calc R . . O7 O 0.8785(3) -0.09581(8) 0.96568(13) 0.0590(5) Uani 1 1 d . . . O8 O 0.3946(2) 0.07594(6) 0.96706(10) 0.0364(4) Uani 1 1 d . . . N9 N 0.5167(2) 0.03722(7) 0.97310(10) 0.0263(3) Uani 1 1 d . . . C15 C 0.7744(3) -0.05569(10) 0.97000(14) 0.0376(5) Uani 1 1 d . . . C16 C 0.7880(3) -0.00629(12) 0.91881(14) 0.0400(6) Uani 1 1 d . . . H16A H 0.7244 -0.0164 0.8732 0.048 Uiso 1 1 calc R . . H16B H 0.9195 0.0000 0.9071 0.048 Uiso 1 1 calc R . . C17 C 0.7069(3) 0.04915(10) 0.94702(14) 0.0337(5) Uani 1 1 d . . . C18 C 0.6240(3) -0.05279(9) 1.02508(13) 0.0345(5) Uani 1 1 d . . . H18A H 0.6748 -0.0361 1.0700 0.041 Uiso 1 1 calc R . . H18B H 0.5838 -0.0919 1.0365 0.041 Uiso 1 1 calc R . . C19 C 0.4550(3) -0.01823(8) 1.00229(12) 0.0262(4) Uani 1 1 d . . . C20 C 0.6957(3) 0.09258(12) 0.88578(17) 0.0480(7) Uani 1 1 d . . . H20A H 0.6118 0.0787 0.8482 0.072 Uiso 1 1 calc R . . H20B H 0.8185 0.0983 0.8650 0.072 Uiso 1 1 calc R . . H20C H 0.6496 0.1287 0.9049 0.072 Uiso 1 1 calc R . . C21 C 0.8188(4) 0.07374(11) 1.01032(17) 0.0462(6) Uani 1 1 d . . . H21A H 0.7610 0.1089 1.0271 0.069 Uiso 1 1 calc R . . H21B H 0.9447 0.0817 0.9941 0.069 Uiso 1 1 calc R . . H21C H 0.8221 0.0462 1.0501 0.069 Uiso 1 1 calc R . . C22 C 0.3335(4) -0.00701(11) 1.06802(15) 0.0416(5) Uani 1 1 d . . . H22A H 0.4050 0.0131 1.1050 0.062 Uiso 1 1 calc R . . H22B H 0.2896 -0.0432 1.0877 0.062 Uiso 1 1 calc R . . H22C H 0.2279 0.0163 1.0536 0.062 Uiso 1 1 calc R . . C23 C 0.3469(3) -0.04871(9) 0.94374(13) 0.0340(5) Uani 1 1 d . . . H23A H 0.2466 -0.0243 0.9268 0.051 Uiso 1 1 calc R . . H23B H 0.2956 -0.0839 0.9634 0.051 Uiso 1 1 calc R . . H23C H 0.4288 -0.0576 0.9031 0.051 Uiso 1 1 calc R . . O1W O 0.98795(19) 0.75628(6) 0.92308(8) 0.0254(3) Uani 1 1 d . . . H1WA H 1.0097 0.7228 0.8948 0.083(12) Uiso 1 1 d R . . H1WB H 0.9265 0.7835 0.8929 0.052(8) Uiso 1 1 d 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 0.01597(16) 0.0201(2) 0.0185(2) 0.00190(17) -0.00219(16) -0.00237(15) S2 0.01735(16) 0.01690(19) 0.0204(2) -0.00074(17) -0.00154(17) 0.00118(15) O1 0.0258(6) 0.0253(7) 0.0220(7) 0.0046(6) -0.0048(5) -0.0044(5) O2 0.0167(5) 0.0243(6) 0.0260(7) 0.0019(5) -0.0030(5) -0.0044(5) O3 0.0208(6) 0.0229(6) 0.0246(7) -0.0015(5) 0.0019(5) -0.0005(5) O4 0.0211(6) 0.0177(6) 0.0301(8) -0.0009(5) -0.0037(5) 0.0005(5) O5 0.0204(6) 0.0218(6) 0.0255(7) 0.0004(5) -0.0049(5) 0.0025(5) O6 0.0229(6) 0.0243(6) 0.0229(7) -0.0001(5) 0.0026(5) 0.0023(5) N1 0.0244(7) 0.0258(8) 0.0209(8) -0.0021(7) 0.0007(6) -0.0042(6) N2 0.0186(7) 0.0234(8) 0.0219(8) -0.0021(6) 0.0008(6) 0.0007(6) C1 0.0139(7) 0.0211(8) 0.0171(9) 0.0002(6) -0.0014(6) 0.0000(6) C2 0.0188(8) 0.0196(8) 0.0214(9) 0.0023(7) -0.0018(7) 0.0001(6) C3 0.0204(8) 0.0227(9) 0.0209(9) 0.0026(7) -0.0006(7) -0.0004(7) C4 0.0177(8) 0.0225(9) 0.0208(9) -0.0009(7) -0.0009(7) -0.0007(7) C5 0.0283(9) 0.0238(9) 0.0246(10) 0.0007(8) 0.0010(8) -0.0097(7) C6 0.0250(8) 0.0251(9) 0.0207(9) 0.0034(7) 0.0012(7) -0.0064(7) C7 0.0151(7) 0.0234(9) 0.0213(9) -0.0016(7) 0.0014(6) 0.0007(7) C8 0.0314(9) 0.0237(9) 0.0217(10) 0.0045(7) -0.0032(8) 0.0000(8) C9 0.0297(9) 0.0170(8) 0.0252(10) 0.0016(7) -0.0038(8) -0.0010(7) C10 0.0138(7) 0.0200(8) 0.0212(9) -0.0006(7) -0.0005(6) -0.0002(6) C11 0.0200(8) 0.0206(8) 0.0213(9) 0.0049(7) 0.0001(7) -0.0006(7) C12 0.0208(8) 0.0169(8) 0.0246(9) 0.0003(7) 0.0001(7) -0.0022(7) C13 0.0218(8) 0.0217(9) 0.0242(10) -0.0016(7) 0.0009(7) 0.0009(7) N3 0.0191(7) 0.0237(8) 0.0381(10) 0.0070(7) 0.0008(7) -0.0010(6) N4 0.0185(7) 0.0246(8) 0.0430(10) 0.0092(7) 0.0003(7) -0.0009(6) N5 0.0197(7) 0.0212(8) 0.0388(10) 0.0046(8) 0.0041(7) 0.0004(6) C14 0.0201(8) 0.0144(8) 0.0260(10) 0.0002(7) -0.0005(7) -0.0011(6) N6 0.0192(7) 0.0273(8) 0.0266(9) -0.0059(7) -0.0026(6) -0.0006(6) N7 0.0172(7) 0.0274(8) 0.0286(9) -0.0089(7) -0.0012(6) 0.0032(6) N8 0.0208(7) 0.0258(8) 0.0253(8) -0.0058(7) -0.0028(6) 0.0024(6) O7 0.0479(11) 0.0548(12) 0.0743(14) -0.0048(11) -0.0092(11) 0.0265(9) O8 0.0429(8) 0.0254(7) 0.0409(9) 0.0045(7) -0.0027(7) 0.0109(6) N9 0.0275(8) 0.0202(7) 0.0312(9) 0.0021(7) -0.0054(7) 0.0011(6) C15 0.0288(10) 0.0383(12) 0.0457(15) -0.0009(11) -0.0117(10) 0.0081(9) C16 0.0264(10) 0.0539(15) 0.0396(13) 0.0011(12) 0.0001(9) 0.0024(10) C17 0.0262(10) 0.0347(12) 0.0402(13) 0.0081(10) -0.0071(9) -0.0076(8) C18 0.0381(11) 0.0260(10) 0.0396(13) 0.0051(9) -0.0097(10) 0.0043(9) C19 0.0302(9) 0.0185(9) 0.0299(11) 0.0027(7) -0.0016(8) 0.0010(7) C20 0.0358(12) 0.0560(16) 0.0523(17) 0.0238(13) -0.0061(11) -0.0113(11) C21 0.0420(13) 0.0397(13) 0.0568(16) 0.0051(12) -0.0215(12) -0.0157(10) C22 0.0512(13) 0.0337(12) 0.0398(14) 0.0059(10) 0.0108(11) 0.0056(10) C23 0.0311(10) 0.0281(11) 0.0427(14) -0.0029(9) -0.0033(9) -0.0039(8) O1W 0.0279(7) 0.0271(7) 0.0213(7) 0.0001(6) -0.0044(6) 0.0031(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O1 1.4563(14) . ? S1 O2 1.4592(13) . ? S1 O3 1.4650(13) . ? S1 C1 1.7609(18) . ? S2 O5 1.4523(13) . ? S2 O6 1.4614(14) . ? S2 O4 1.4654(14) . ? S2 C10 1.7635(19) . ? N1 N2 1.254(2) . ? N1 C4 1.421(2) . ? N2 C7 1.436(2) . ? C1 C6 1.385(3) . ? C1 C2 1.390(3) . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? C3 C4 1.392(3) . ? C3 H3 0.9500 . ? C4 C5 1.395(3) . ? C5 C6 1.387(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C12 1.383(3) . ? C7 C8 1.397(3) . ? C8 C9 1.376(3) . ? C8 H8 0.9500 . ? C9 C10 1.391(3) . ? C9 H9 0.9500 . ? C10 C11 1.395(2) . ? C11 C12 1.384(3) . ? C11 H11 0.9500 . ? C12 H12 0.9500 . ? C13 N5 1.325(3) . ? C13 N4 1.328(2) . ? C13 N3 1.329(2) . ? N3 H3A 0.8800 . ? N3 H3B 0.8800 . ? N4 H4A 0.8800 . ? N4 H4B 0.8800 . ? N5 H5A 0.8800 . ? N5 H5B 0.8800 . ? C14 N8 1.319(2) . ? C14 N6 1.323(2) . ? C14 N7 1.329(3) . ? N6 H6A 0.8800 . ? N6 H6B 0.8800 . ? N7 H7A 0.8800 . ? N7 H7B 0.8800 . ? N8 H8A 0.8800 . ? N8 H8B 0.8800 . ? O7 C15 1.214(3) . ? O8 N9 1.277(2) . ? N9 C19 1.484(2) . ? N9 C17 1.490(3) . ? C15 C18 1.494(4) . ? C15 C16 1.504(4) . ? C16 C17 1.526(4) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C20 1.528(3) . ? C17 C21 1.538(3) . ? C18 C19 1.532(3) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C23 1.517(3) . ? C19 C22 1.524(3) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? O1W H1WA 0.9599 . ? O1W H1WB 0.9602 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 S1 O2 113.50(8) . . ? O1 S1 O3 112.06(8) . . ? O2 S1 O3 111.62(7) . . ? O1 S1 C1 106.47(8) . . ? O2 S1 C1 106.46(8) . . ? O3 S1 C1 106.15(8) . . ? O5 S2 O6 113.02(8) . . ? O5 S2 O4 112.49(8) . . ? O6 S2 O4 111.88(8) . . ? O5 S2 C10 106.79(8) . . ? O6 S2 C10 105.96(8) . . ? O4 S2 C10 106.10(8) . . ? N2 N1 C4 113.63(15) . . ? N1 N2 C7 113.43(14) . . ? C6 C1 C2 120.84(17) . . ? C6 C1 S1 119.89(14) . . ? C2 C1 S1 119.27(14) . . ? C3 C2 C1 120.10(17) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 119.38(18) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C4 C5 120.45(18) . . ? C3 C4 N1 123.34(17) . . ? C5 C4 N1 116.16(16) . . ? C6 C5 C4 119.88(17) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C1 C6 C5 119.30(18) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C12 C7 C8 120.64(18) . . ? C12 C7 N2 116.12(16) . . ? C8 C7 N2 123.23(17) . . ? C9 C8 C7 119.15(18) . . ? C9 C8 H8 120.4 . . ? C7 C8 H8 120.4 . . ? C8 C9 C10 120.22(17) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C9 C10 C11 120.73(17) . . ? C9 C10 S2 120.55(13) . . ? C11 C10 S2 118.72(14) . . ? C12 C11 C10 118.76(17) . . ? C12 C11 H11 120.6 . . ? C10 C11 H11 120.6 . . ? C7 C12 C11 120.48(16) . . ? C7 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? N5 C13 N4 120.02(17) . . ? N5 C13 N3 120.17(17) . . ? N4 C13 N3 119.80(18) . . ? C13 N3 H3A 120.0 . . ? C13 N3 H3B 120.0 . . ? H3A N3 H3B 120.0 . . ? C13 N4 H4A 120.0 . . ? C13 N4 H4B 120.0 . . ? H4A N4 H4B 120.0 . . ? C13 N5 H5A 120.0 . . ? C13 N5 H5B 120.0 . . ? H5A N5 H5B 120.0 . . ? N8 C14 N6 120.10(17) . . ? N8 C14 N7 120.00(17) . . ? N6 C14 N7 119.90(17) . . ? C14 N6 H6A 120.0 . . ? C14 N6 H6B 120.0 . . ? H6A N6 H6B 120.0 . . ? C14 N7 H7A 120.0 . . ? C14 N7 H7B 120.0 . . ? H7A N7 H7B 120.0 . . ? C14 N8 H8A 120.0 . . ? C14 N8 H8B 120.0 . . ? H8A N8 H8B 120.0 . . ? O8 N9 C19 116.92(16) . . ? O8 N9 C17 118.68(17) . . ? C19 N9 C17 124.30(16) . . ? O7 C15 C18 122.4(2) . . ? O7 C15 C16 121.4(2) . . ? C18 C15 C16 116.16(19) . . ? C15 C16 C17 115.1(2) . . ? 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 . . ? N9 C17 C16 107.86(18) . . ? N9 C17 C20 108.47(17) . . ? C16 C17 C20 110.0(2) . . ? N9 C17 C21 108.4(2) . . ? C16 C17 C21 112.3(2) . . ? C20 C17 C21 109.8(2) . . ? C15 C18 C19 114.99(19) . . ? C15 C18 H18A 108.5 . . ? C19 C18 H18A 108.5 . . ? C15 C18 H18B 108.5 . . ? C19 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? N9 C19 C23 108.33(17) . . ? N9 C19 C22 108.13(17) . . ? C23 C19 C22 110.53(19) . . ? N9 C19 C18 109.10(16) . . ? C23 C19 C18 110.99(18) . . ? C22 C19 C18 109.69(19) . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C19 C23 H23A 109.5 . . ? C19 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C19 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? H1WA O1W H1WB 108.1 . . ? 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 N3 H3A O4 0.88 2.04 2.919(2) 173.3 4_544 N3 H3B O2 0.88 2.08 2.948(2) 167.8 . N4 H4A O4 0.88 2.03 2.912(2) 176.5 4_644 N4 H4B O3 0.88 2.02 2.897(2) 175.8 . N5 H5A O5 0.88 2.04 2.916(2) 172.8 4_644 N5 H5B O6 0.88 2.09 2.956(2) 169.9 4_544 N6 H6A O1W 0.88 2.10 2.909(2) 152.3 1_454 N6 H6B O1 0.88 2.24 3.055(2) 154.6 3_465 N7 H7A O2 0.88 2.15 2.957(2) 151.3 3_565 N7 H7B O3 0.88 2.07 2.921(2) 163.3 3_465 N8 H8A O1W 0.88 2.03 2.891(2) 167.5 3_464 N8 H8B O1 0.88 2.03 2.904(2) 169.7 3_565 O1W H1WA O6 0.96 1.87 2.8223(19) 173.6 3_565 O1W H1WB O5 0.96 1.92 2.8443(19) 161.1 . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 30.56 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.435 _refine_diff_density_min -0.215 _refine_diff_density_rms 0.058