# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_L1 _database_code_depnum_ccdc_archive 'CCDC 899407' #TrackingRef 'all-cif-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H11 N5 O5 S' _chemical_formula_weight 361.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0296(13) _cell_length_b 10.7993(10) _cell_length_c 15.4635(16) _cell_angle_alpha 90.00 _cell_angle_beta 129.493(6) _cell_angle_gamma 90.00 _cell_volume 1550.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3042 _cell_measurement_theta_min 1.86 _cell_measurement_theta_max 20.52 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.933 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12475 _diffrn_reflns_av_R_equivalents 0.0672 _diffrn_reflns_av_sigmaI/netI 0.0720 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 24.77 _reflns_number_total 2619 _reflns_number_gt 1362 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0462P)^2^+2.1306P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2619 _refine_ls_number_parameters 226 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1293 _refine_ls_R_factor_gt 0.0508 _refine_ls_wR_factor_ref 0.1485 _refine_ls_wR_factor_gt 0.1083 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_restrained_S_all 0.998 _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 1.04571(15) 0.70672(10) 0.32594(10) 0.0571(4) Uani 1 1 d . . . O1 O 0.8121(3) 0.4473(3) 0.4052(2) 0.0559(9) Uani 1 1 d . . . O5 O 0.6045(4) 0.1394(3) 0.5010(3) 0.0732(10) Uani 1 1 d . . . O4 O 0.4351(5) 0.0324(4) 0.3588(3) 0.0958(13) Uani 1 1 d . . . O3 O 0.5662(5) -0.1336(4) 0.1382(4) 0.1085(15) Uani 1 1 d . . . O2 O 0.6736(6) -0.0127(4) 0.1030(5) 0.142(2) Uani 1 1 d . . . N1 N 0.8623(4) 0.5399(3) 0.1718(3) 0.0571(11) Uani 1 1 d . . . H1N H 0.8212 0.4676 0.1530 0.069 Uiso 1 1 d R . . N2 N 0.9832(4) 0.4876(3) 0.3548(3) 0.0487(10) Uani 1 1 d . . . H2N H 1.0413 0.5054 0.4302 0.058 Uiso 1 1 d R . . N3 N 0.8996(4) 0.3796(3) 0.3213(3) 0.0452(9) Uani 1 1 d . . . H3N H 0.9251 0.3180 0.2990 0.054 Uiso 1 1 d R . . N5 N 0.5447(5) 0.0948(4) 0.4090(4) 0.0610(11) Uani 1 1 d . . . N4 N 0.6271(5) -0.0368(4) 0.1513(4) 0.0832(15) Uani 1 1 d . . . C1 C 0.8312(5) 0.6141(4) 0.0818(3) 0.0456(11) Uani 1 1 d . . . C2 C 0.9063(5) 0.5945(4) 0.0443(4) 0.0600(13) Uani 1 1 d . . . H2 H 0.9761 0.5328 0.0765 0.072 Uiso 1 1 calc R . . C3 C 0.8788(6) 0.6665(5) -0.0415(4) 0.0701(15) Uani 1 1 d . . . H3 H 0.9288 0.6521 -0.0679 0.084 Uiso 1 1 calc R . . C4 C 0.7788(7) 0.7581(5) -0.0871(4) 0.0720(16) Uani 1 1 d . . . H4 H 0.7604 0.8070 -0.1444 0.086 Uiso 1 1 calc R . . C5 C 0.7066(7) 0.7773(5) -0.0486(5) 0.0853(18) Uani 1 1 d . . . H5 H 0.6391 0.8408 -0.0794 0.102 Uiso 1 1 calc R . . C6 C 0.7301(6) 0.7054(5) 0.0355(4) 0.0713(15) Uani 1 1 d . . . H6 H 0.6779 0.7191 0.0602 0.086 Uiso 1 1 calc R . . C7 C 0.9563(5) 0.5711(3) 0.2787(4) 0.0432(11) Uani 1 1 d . . . C8 C 0.8207(5) 0.3669(4) 0.3545(3) 0.0449(11) Uani 1 1 d . . . C9 C 0.7395(5) 0.2466(3) 0.3248(3) 0.0429(11) Uani 1 1 d . . . C10 C 0.7204(5) 0.1609(4) 0.2490(4) 0.0499(12) Uani 1 1 d . . . H10 H 0.7580 0.1750 0.2127 0.060 Uiso 1 1 calc R . . C11 C 0.6433(5) 0.0535(4) 0.2290(4) 0.0547(12) Uani 1 1 d . . . C12 C 0.5829(5) 0.0304(4) 0.2776(4) 0.0566(13) Uani 1 1 d . . . H12 H 0.5281 -0.0403 0.2603 0.068 Uiso 1 1 calc R . . C13 C 0.6061(5) 0.1157(4) 0.3533(4) 0.0474(11) Uani 1 1 d . . . C14 C 0.6850(4) 0.2236(4) 0.3788(3) 0.0451(11) Uani 1 1 d . . . H14 H 0.7005 0.2791 0.4315 0.054 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0890(9) 0.0353(6) 0.0619(7) -0.0085(5) 0.0550(7) -0.0181(6) O1 0.088(2) 0.0340(16) 0.064(2) -0.0064(15) 0.057(2) -0.0018(16) O5 0.099(3) 0.066(2) 0.075(3) 0.0140(19) 0.065(2) 0.004(2) O4 0.089(3) 0.115(3) 0.098(3) 0.003(3) 0.066(3) -0.035(3) O3 0.150(4) 0.061(2) 0.149(4) -0.046(3) 0.110(4) -0.049(3) O2 0.236(6) 0.089(3) 0.218(6) -0.089(3) 0.200(6) -0.081(4) N1 0.086(3) 0.0297(19) 0.049(2) -0.0013(16) 0.040(2) -0.0135(19) N2 0.072(3) 0.0296(18) 0.049(2) -0.0030(16) 0.041(2) -0.0121(18) N3 0.070(3) 0.0200(17) 0.060(2) -0.0048(15) 0.049(2) -0.0060(16) N5 0.071(3) 0.053(3) 0.068(3) 0.020(2) 0.049(3) 0.006(2) N4 0.117(4) 0.047(3) 0.118(4) -0.033(3) 0.090(4) -0.031(3) C1 0.063(3) 0.026(2) 0.046(3) -0.0005(19) 0.034(3) -0.006(2) C2 0.076(3) 0.043(3) 0.070(3) 0.004(2) 0.051(3) 0.002(2) C3 0.106(4) 0.057(3) 0.077(4) -0.005(3) 0.072(4) -0.011(3) C4 0.113(5) 0.042(3) 0.060(3) 0.003(2) 0.054(4) -0.012(3) C5 0.109(5) 0.067(4) 0.088(4) 0.035(3) 0.067(4) 0.037(3) C6 0.089(4) 0.066(3) 0.076(4) 0.017(3) 0.061(3) 0.022(3) C7 0.062(3) 0.030(2) 0.051(3) 0.004(2) 0.042(3) 0.000(2) C8 0.065(3) 0.028(2) 0.052(3) 0.0043(19) 0.042(3) 0.002(2) C9 0.057(3) 0.027(2) 0.054(3) 0.0016(18) 0.039(2) 0.0007(19) C10 0.066(3) 0.036(2) 0.062(3) -0.001(2) 0.048(3) -0.002(2) C11 0.068(3) 0.033(2) 0.070(3) -0.009(2) 0.047(3) -0.009(2) C12 0.065(3) 0.038(3) 0.066(3) 0.004(2) 0.041(3) -0.007(2) C13 0.051(3) 0.044(3) 0.052(3) 0.014(2) 0.035(3) 0.004(2) C14 0.057(3) 0.037(2) 0.048(2) 0.004(2) 0.036(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 C7 1.684(4) . ? O1 C8 1.217(5) . ? O5 N5 1.213(5) . ? O4 N5 1.222(5) . ? O3 N4 1.217(5) . ? O2 N4 1.212(6) . ? N1 C7 1.322(5) . ? N1 C1 1.435(5) . ? N1 H1N 0.8688 . ? N2 C7 1.349(5) . ? N2 N3 1.406(4) . ? N2 H2N 0.9209 . ? N3 C8 1.342(5) . ? N3 H3N 0.8887 . ? N5 C13 1.466(6) . ? N4 C11 1.462(6) . ? C1 C6 1.363(6) . ? C1 C2 1.365(6) . ? C2 C3 1.384(6) . ? C2 H2 0.9300 . ? C3 C4 1.358(7) . ? C3 H3 0.9300 . ? C4 C5 1.345(7) . ? C4 H4 0.9300 . ? C5 C6 1.381(7) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C8 C9 1.511(6) . ? C9 C14 1.373(5) . ? C9 C10 1.394(5) . ? C10 C11 1.391(6) . ? C10 H10 0.9300 . ? C11 C12 1.360(6) . ? C12 C13 1.370(6) . ? C12 H12 0.9300 . ? C13 C14 1.392(6) . ? C14 H14 0.9300 . ? 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 C7 N1 C1 123.9(3) . . ? C7 N1 H1N 120.0 . . ? C1 N1 H1N 115.8 . . ? C7 N2 N3 120.9(3) . . ? C7 N2 H2N 122.2 . . ? N3 N2 H2N 115.4 . . ? C8 N3 N2 117.2(3) . . ? C8 N3 H3N 125.0 . . ? N2 N3 H3N 114.9 . . ? O5 N5 O4 124.0(5) . . ? O5 N5 C13 118.9(4) . . ? O4 N5 C13 117.0(4) . . ? O2 N4 O3 123.2(5) . . ? O2 N4 C11 119.4(4) . . ? O3 N4 C11 117.4(5) . . ? C6 C1 C2 120.0(4) . . ? C6 C1 N1 120.5(4) . . ? C2 C1 N1 119.4(4) . . ? C1 C2 C3 120.1(5) . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 119.9(5) . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 119.4(5) . . ? C5 C4 H4 120.3 . . ? C3 C4 H4 120.3 . . ? C4 C5 C6 121.8(5) . . ? C4 C5 H5 119.1 . . ? C6 C5 H5 119.1 . . ? C1 C6 C5 118.7(5) . . ? C1 C6 H6 120.7 . . ? C5 C6 H6 120.7 . . ? N1 C7 N2 117.4(4) . . ? N1 C7 S1 124.5(3) . . ? N2 C7 S1 118.1(3) . . ? O1 C8 N3 123.0(4) . . ? O1 C8 C9 120.3(4) . . ? N3 C8 C9 116.7(4) . . ? C14 C9 C10 120.3(4) . . ? C14 C9 C8 116.0(4) . . ? C10 C9 C8 123.7(4) . . ? C11 C10 C9 118.0(4) . . ? C11 C10 H10 121.0 . . ? C9 C10 H10 121.0 . . ? C12 C11 C10 123.1(4) . . ? C12 C11 N4 119.6(4) . . ? C10 C11 N4 117.4(4) . . ? C11 C12 C13 117.3(4) . . ? C11 C12 H12 121.4 . . ? C13 C12 H12 121.4 . . ? C12 C13 C14 122.5(4) . . ? C12 C13 N5 119.5(4) . . ? C14 C13 N5 118.0(4) . . ? C9 C14 C13 118.8(4) . . ? C9 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? 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 N2 N3 C8 -115.8(4) . . . . ? C7 N1 C1 C6 -86.5(6) . . . . ? C7 N1 C1 C2 92.0(5) . . . . ? C6 C1 C2 C3 -0.7(7) . . . . ? N1 C1 C2 C3 -179.2(4) . . . . ? C1 C2 C3 C4 1.2(7) . . . . ? C2 C3 C4 C5 -0.4(8) . . . . ? C3 C4 C5 C6 -0.8(9) . . . . ? C2 C1 C6 C5 -0.5(7) . . . . ? N1 C1 C6 C5 178.0(5) . . . . ? C4 C5 C6 C1 1.2(9) . . . . ? C1 N1 C7 N2 -174.6(4) . . . . ? C1 N1 C7 S1 4.6(6) . . . . ? N3 N2 C7 N1 -9.0(6) . . . . ? N3 N2 C7 S1 171.8(3) . . . . ? N2 N3 C8 O1 4.9(6) . . . . ? N2 N3 C8 C9 -175.8(3) . . . . ? O1 C8 C9 C14 -14.1(6) . . . . ? N3 C8 C9 C14 166.6(4) . . . . ? O1 C8 C9 C10 166.8(4) . . . . ? N3 C8 C9 C10 -12.5(6) . . . . ? C14 C9 C10 C11 0.9(6) . . . . ? C8 C9 C10 C11 180.0(4) . . . . ? C9 C10 C11 C12 1.9(7) . . . . ? C9 C10 C11 N4 -178.6(4) . . . . ? O2 N4 C11 C12 175.6(6) . . . . ? O3 N4 C11 C12 -4.1(7) . . . . ? O2 N4 C11 C10 -3.9(8) . . . . ? O3 N4 C11 C10 176.3(5) . . . . ? C10 C11 C12 C13 -3.0(7) . . . . ? N4 C11 C12 C13 177.4(4) . . . . ? C11 C12 C13 C14 1.5(7) . . . . ? C11 C12 C13 N5 -179.4(4) . . . . ? O5 N5 C13 C12 152.6(4) . . . . ? O4 N5 C13 C12 -27.2(6) . . . . ? O5 N5 C13 C14 -28.2(6) . . . . ? O4 N5 C13 C14 151.9(4) . . . . ? C10 C9 C14 C13 -2.4(6) . . . . ? C8 C9 C14 C13 178.5(4) . . . . ? C12 C13 C14 C9 1.2(6) . . . . ? N5 C13 C14 C9 -178.0(4) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 24.77 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.322 _refine_diff_density_min -0.301 _refine_diff_density_rms 0.058 data_salt1 _database_code_depnum_ccdc_archive 'CCDC 899408' #TrackingRef 'all-cif-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H46 N6 O5 S' _chemical_formula_weight 602.80 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' F F 0.0171 0.0103 '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 7.9913(2) _cell_length_b 12.2522(4) _cell_length_c 17.6848(5) _cell_angle_alpha 78.780(2) _cell_angle_beta 89.551(2) _cell_angle_gamma 76.168(2) _cell_volume 1647.83(8) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.65 _cell_measurement_theta_max 21.26 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.215 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.144 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16373 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 27.40 _reflns_number_total 7464 _reflns_number_gt 4843 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0707P)^2^+0.2170P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0081(14) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6466 _refine_ls_number_parameters 392 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1313 _refine_ls_wR_factor_gt 0.1137 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 0.73032(7) 0.96854(4) 0.10979(2) 0.03564(15) Uani 1 1 d . . . C9 C 0.8253(2) 0.71020(14) 0.45153(9) 0.0262(4) Uani 1 1 d . . . C10 C 0.7555(2) 0.61595(14) 0.45441(9) 0.0257(4) Uani 1 1 d . . . H10 H 0.6965 0.6078 0.4115 0.031 Uiso 1 1 calc R . . C12 C 0.8622(2) 0.54163(15) 0.58748(9) 0.0303(4) Uani 1 1 d . . . H12 H 0.8741 0.4859 0.6324 0.036 Uiso 1 1 calc R . . C14 C 0.9129(2) 0.72044(14) 0.51656(9) 0.0275(4) Uani 1 1 d . . . H14 H 0.9593 0.7834 0.5157 0.033 Uiso 1 1 calc R . . C28 C 0.1777(2) -0.15640(14) 0.23364(9) 0.0290(4) Uani 1 1 d . . . H28A H 0.0811 -0.1158 0.1981 0.035 Uiso 1 1 calc R . . H28B H 0.1342 -0.1698 0.2851 0.035 Uiso 1 1 calc R . . C8 C 0.8126(2) 0.80201(14) 0.37979(9) 0.0261(4) Uani 1 1 d . . . C11 C 0.7751(2) 0.53447(14) 0.52193(9) 0.0275(4) Uani 1 1 d . . . C7 C 0.7215(2) 0.85808(14) 0.18177(9) 0.0264(4) Uani 1 1 d . . . C13 C 0.9302(2) 0.63567(15) 0.58247(9) 0.0287(4) Uani 1 1 d . . . C27 C 0.3071(2) -0.08398(14) 0.23133(9) 0.0287(4) Uani 1 1 d . . . H27A H 0.3442 -0.0679 0.1788 0.034 Uiso 1 1 calc R . . H27B H 0.4075 -0.1288 0.2634 0.034 Uiso 1 1 calc R . . C15 C 0.0831(2) 0.10238(15) 0.21227(9) 0.0289(4) Uani 1 1 d . . . H15A H 0.0476 0.1729 0.2317 0.035 Uiso 1 1 calc R . . H15B H -0.0078 0.0620 0.2226 0.035 Uiso 1 1 calc R . . C29 C 0.2607(2) -0.27094(15) 0.21162(10) 0.0333(4) Uani 1 1 d . . . H29A H 0.3162 -0.2573 0.1629 0.040 Uiso 1 1 calc R . . H29B H 0.3487 -0.3150 0.2505 0.040 Uiso 1 1 calc R . . C1 C 0.6623(2) 0.71553(15) 0.10776(9) 0.0283(4) Uani 1 1 d . . . C19 C 0.3918(2) 0.08894(15) 0.24672(10) 0.0297(4) Uani 1 1 d . . . H19A H 0.4891 0.0410 0.2794 0.036 Uiso 1 1 calc R . . H19B H 0.4260 0.0924 0.1937 0.036 Uiso 1 1 calc R . . C24 C 0.3349(2) -0.06938(15) 0.39924(9) 0.0311(4) Uani 1 1 d . . . H24A H 0.4404 -0.0431 0.3936 0.037 Uiso 1 1 calc R . . H24B H 0.3588 -0.1467 0.3894 0.037 Uiso 1 1 calc R . . C20 C 0.3599(3) 0.20856(15) 0.26322(10) 0.0347(4) Uani 1 1 d . . . H20A H 0.3327 0.2069 0.3169 0.042 Uiso 1 1 calc R . . H20B H 0.2624 0.2585 0.2315 0.042 Uiso 1 1 calc R . . C30 C 0.1286(3) -0.33949(16) 0.20442(11) 0.0388(5) Uani 1 1 d . . . H30A H 0.0709 -0.3510 0.2521 0.058 Uiso 1 1 calc R . . H30C H 0.1857 -0.4125 0.1931 0.058 Uiso 1 1 calc R . . H30B H 0.0457 -0.2983 0.1635 0.058 Uiso 1 1 calc R . . C23 C 0.1967(2) 0.00917(14) 0.34220(9) 0.0290(4) Uani 1 1 d . . . H23A H 0.1638 0.0829 0.3577 0.035 Uiso 1 1 calc R . . H23B H 0.0960 -0.0225 0.3460 0.035 Uiso 1 1 calc R . . C25 C 0.2723(3) -0.06893(17) 0.48073(9) 0.0385(5) Uani 1 1 d . . . H25A H 0.2442 0.0092 0.4891 0.046 Uiso 1 1 calc R . . H25B H 0.1677 -0.0964 0.4859 0.046 Uiso 1 1 calc R . . C21 C 0.5201(3) 0.25478(16) 0.24592(10) 0.0358(5) Uani 1 1 d . . . H21A H 0.6187 0.2008 0.2746 0.043 Uiso 1 1 calc R . . H21B H 0.5418 0.2606 0.1914 0.043 Uiso 1 1 calc R . . C6 C 0.5698(2) 0.78487(16) 0.04230(9) 0.0318(4) Uani 1 1 d . . . H6 H 0.5234 0.8625 0.0409 0.038 Uiso 1 1 calc R . . C17 C -0.0662(3) 0.22060(16) 0.09067(10) 0.0369(5) Uani 1 1 d . . . H17A H -0.1653 0.1908 0.1074 0.044 Uiso 1 1 calc R . . H17B H -0.0753 0.2906 0.1100 0.044 Uiso 1 1 calc R . . C16 C 0.0964(3) 0.13372(16) 0.12555(9) 0.0363(5) Uani 1 1 d . . . H16A H 0.1957 0.1657 0.1137 0.044 Uiso 1 1 calc R . . H16B H 0.1119 0.0655 0.1036 0.044 Uiso 1 1 calc R . . C5 C 0.5475(3) 0.73749(16) -0.02040(10) 0.0371(5) Uani 1 1 d . . . H5 H 0.4871 0.7840 -0.0644 0.044 Uiso 1 1 calc R . . C26 C 0.4051(3) -0.14298(17) 0.54188(11) 0.0477(6) Uani 1 1 d . . . H26A H 0.4300 -0.2210 0.5351 0.072 Uiso 1 1 calc R . . H26B H 0.3606 -0.1387 0.5921 0.072 Uiso 1 1 calc R . . H26C H 0.5088 -0.1161 0.5372 0.072 Uiso 1 1 calc R . . C2 C 0.7268(3) 0.60003(16) 0.10977(11) 0.0462(6) Uani 1 1 d . . . H2 H 0.7872 0.5531 0.1536 0.055 Uiso 1 1 calc R . . C4 C 0.6126(3) 0.62322(18) -0.01894(12) 0.0555(6) Uani 1 1 d . . . H4 H 0.5970 0.5924 -0.0617 0.067 Uiso 1 1 calc R . . C22 C 0.5031(3) 0.37169(18) 0.26674(14) 0.0535(6) Uani 1 1 d . . . H22B H 0.4065 0.4258 0.2382 0.080 Uiso 1 1 calc R . . H22A H 0.6065 0.3970 0.2542 0.080 Uiso 1 1 calc R . . H22C H 0.4856 0.3660 0.3210 0.080 Uiso 1 1 calc R . . C18 C -0.0711(3) 0.2488(2) 0.00359(11) 0.0531(6) Uani 1 1 d . . . H18A H 0.0228 0.2826 -0.0135 0.080 Uiso 1 1 calc R . . H18B H -0.1784 0.3019 -0.0151 0.080 Uiso 1 1 calc R . . H18C H -0.0607 0.1798 -0.0160 0.080 Uiso 1 1 calc R . . C3 C 0.7018(4) 0.55401(18) 0.04640(13) 0.0660(8) Uani 1 1 d . . . H3 H 0.7452 0.4761 0.0479 0.079 Uiso 1 1 calc R . . N1 N 0.6878(2) 0.75683(13) 0.17522(8) 0.0286(3) Uani 1 1 d . . . N3 N 0.75444(19) 0.77516(12) 0.31737(7) 0.0271(3) Uani 1 1 d . . . N2 N 0.7505(2) 0.86555(13) 0.25490(8) 0.0283(3) Uani 1 1 d . . . N5 N 1.0278(2) 0.64545(14) 0.65046(8) 0.0362(4) Uani 1 1 d . . . N4 N 0.7037(2) 0.43377(13) 0.52425(9) 0.0342(4) Uani 1 1 d . . . O1 O 0.85740(18) 0.89230(10) 0.38370(6) 0.0355(3) Uani 1 1 d . . . O2 O 0.64647(18) 0.42003(11) 0.46356(7) 0.0410(3) Uani 1 1 d . . . O5 O 1.07580(19) 0.73341(11) 0.64853(7) 0.0421(4) Uani 1 1 d . . . O3 O 0.7060(2) 0.36836(12) 0.58649(8) 0.0520(4) Uani 1 1 d . . . O4 O 1.0544(2) 0.56519(14) 0.70563(8) 0.0663(5) Uani 1 1 d . . . N6 N 0.24424(19) 0.02955(12) 0.25784(7) 0.0268(3) Uani 1 1 d . . . H1N H 0.709(3) 0.7054(17) 0.2191(11) 0.041(5) Uiso 1 1 d . . . H2N H 0.787(3) 0.9240(17) 0.2658(11) 0.046(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0386(3) 0.0325(3) 0.0326(2) 0.00238(18) 0.00200(19) -0.0096(2) C9 0.0221(10) 0.0291(9) 0.0268(8) -0.0068(7) 0.0043(7) -0.0043(8) C10 0.0208(10) 0.0311(9) 0.0269(8) -0.0090(7) 0.0029(7) -0.0071(8) C12 0.0283(11) 0.0333(9) 0.0276(8) -0.0033(7) 0.0036(7) -0.0062(8) C14 0.0247(11) 0.0289(9) 0.0305(8) -0.0099(7) 0.0040(7) -0.0068(8) C28 0.0223(11) 0.0338(9) 0.0309(8) -0.0056(7) 0.0032(7) -0.0075(8) C8 0.0212(10) 0.0283(9) 0.0291(8) -0.0066(7) 0.0056(7) -0.0062(8) C11 0.0234(11) 0.0287(9) 0.0323(8) -0.0082(7) 0.0058(7) -0.0083(8) C7 0.0175(10) 0.0293(9) 0.0303(8) -0.0023(7) 0.0020(7) -0.0043(8) C13 0.0257(11) 0.0354(9) 0.0255(8) -0.0091(7) 0.0005(7) -0.0057(8) C27 0.0235(11) 0.0322(9) 0.0299(8) -0.0087(7) 0.0032(7) -0.0036(8) C15 0.0216(11) 0.0318(9) 0.0312(8) -0.0041(7) 0.0007(7) -0.0043(8) C29 0.0259(12) 0.0329(10) 0.0402(9) -0.0078(8) 0.0006(8) -0.0047(8) C1 0.0241(11) 0.0346(9) 0.0273(8) -0.0011(7) 0.0013(7) -0.0135(8) C19 0.0232(11) 0.0335(9) 0.0314(8) -0.0037(7) 0.0021(7) -0.0075(8) C24 0.0332(12) 0.0304(9) 0.0302(8) -0.0069(7) 0.0012(7) -0.0080(8) C20 0.0292(12) 0.0338(10) 0.0410(10) -0.0069(8) -0.0018(8) -0.0074(9) C30 0.0339(13) 0.0317(10) 0.0498(11) -0.0057(8) -0.0016(9) -0.0076(9) C23 0.0292(11) 0.0319(9) 0.0272(8) -0.0076(7) 0.0062(7) -0.0085(8) C25 0.0426(13) 0.0459(11) 0.0295(9) -0.0070(8) 0.0025(8) -0.0162(10) C21 0.0358(13) 0.0406(10) 0.0317(9) -0.0021(8) -0.0029(8) -0.0147(9) C6 0.0251(11) 0.0358(10) 0.0321(9) -0.0011(7) 0.0020(7) -0.0071(8) C17 0.0369(13) 0.0371(10) 0.0334(9) -0.0019(8) -0.0004(8) -0.0069(9) C16 0.0302(12) 0.0456(11) 0.0308(9) -0.0045(8) 0.0031(8) -0.0071(9) C5 0.0382(13) 0.0429(11) 0.0291(9) -0.0008(8) -0.0032(8) -0.0130(9) C26 0.0691(17) 0.0430(12) 0.0323(10) -0.0032(8) -0.0071(10) -0.0193(11) C2 0.0619(16) 0.0341(10) 0.0387(10) 0.0006(8) -0.0166(10) -0.0099(10) C4 0.0799(19) 0.0456(12) 0.0423(11) -0.0104(10) -0.0179(11) -0.0159(12) C22 0.0489(16) 0.0381(11) 0.0737(15) -0.0040(10) -0.0118(12) -0.0164(11) C18 0.0466(15) 0.0672(15) 0.0342(10) -0.0010(10) -0.0026(9) 0.0006(12) C3 0.105(2) 0.0307(11) 0.0581(14) -0.0106(10) -0.0279(14) -0.0057(12) N1 0.0286(10) 0.0318(8) 0.0234(7) 0.0007(6) -0.0005(6) -0.0085(7) N3 0.0252(9) 0.0288(7) 0.0259(7) -0.0014(6) 0.0013(6) -0.0070(6) N2 0.0264(10) 0.0287(8) 0.0285(7) -0.0024(6) 0.0007(6) -0.0069(7) N5 0.0350(11) 0.0449(9) 0.0293(8) -0.0082(7) -0.0014(7) -0.0101(8) N4 0.0302(10) 0.0324(8) 0.0405(8) -0.0055(7) 0.0023(7) -0.0102(7) O1 0.0466(9) 0.0312(7) 0.0329(6) -0.0074(5) 0.0037(6) -0.0168(6) O2 0.0433(9) 0.0395(7) 0.0467(8) -0.0134(6) 0.0007(6) -0.0186(7) O5 0.0464(10) 0.0410(8) 0.0429(7) -0.0174(6) -0.0066(6) -0.0104(7) O3 0.0650(12) 0.0437(8) 0.0478(8) 0.0081(6) -0.0020(7) -0.0281(8) O4 0.0868(14) 0.0763(11) 0.0374(8) 0.0144(7) -0.0242(8) -0.0424(10) N6 0.0222(9) 0.0313(8) 0.0268(7) -0.0054(6) 0.0023(6) -0.0067(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C7 1.6825(16) . ? C9 C10 1.390(2) . ? C9 C14 1.393(2) . ? C9 C8 1.509(2) . ? C10 C11 1.383(2) . ? C12 C13 1.375(2) . ? C12 C11 1.385(2) . ? C14 C13 1.385(2) . ? C28 C27 1.511(3) . ? C28 C29 1.525(2) . ? C8 O1 1.255(2) . ? C8 N3 1.329(2) . ? C11 N4 1.471(2) . ? C7 N2 1.340(2) . ? C7 N1 1.357(2) . ? C13 N5 1.478(2) . ? C27 N6 1.524(2) . ? C15 N6 1.513(2) . ? C15 C16 1.516(2) . ? C29 C30 1.518(3) . ? C1 C2 1.379(3) . ? C1 C6 1.392(2) . ? C1 N1 1.417(2) . ? C19 C20 1.512(2) . ? C19 N6 1.520(2) . ? C24 C23 1.515(2) . ? C24 C25 1.522(2) . ? C20 C21 1.525(3) . ? C23 N6 1.524(2) . ? C25 C26 1.515(3) . ? C21 C22 1.522(3) . ? C6 C5 1.379(2) . ? C17 C18 1.510(2) . ? C17 C16 1.516(3) . ? C5 C4 1.367(3) . ? C2 C3 1.385(3) . ? C4 C3 1.380(3) . ? N3 N2 1.3984(18) . ? N5 O5 1.2218(19) . ? N5 O4 1.2223(19) . ? N4 O2 1.2265(18) . ? N4 O3 1.2265(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C10 C9 C14 119.36(15) . . ? C10 C9 C8 122.52(15) . . ? C14 C9 C8 118.12(15) . . ? C11 C10 C9 119.05(15) . . ? C13 C12 C11 116.29(15) . . ? C13 C14 C9 119.19(16) . . ? C27 C28 C29 110.55(15) . . ? O1 C8 N3 126.97(15) . . ? O1 C8 C9 119.34(14) . . ? N3 C8 C9 113.68(14) . . ? C10 C11 C12 123.10(16) . . ? C10 C11 N4 118.85(15) . . ? C12 C11 N4 118.03(15) . . ? N2 C7 N1 113.24(14) . . ? N2 C7 S1 119.60(14) . . ? N1 C7 S1 127.16(13) . . ? C12 C13 C14 123.01(15) . . ? C12 C13 N5 118.14(15) . . ? C14 C13 N5 118.85(16) . . ? C28 C27 N6 115.91(14) . . ? N6 C15 C16 116.80(14) . . ? C30 C29 C28 111.54(16) . . ? C2 C1 C6 119.66(16) . . ? C2 C1 N1 117.26(15) . . ? C6 C1 N1 123.02(16) . . ? C20 C19 N6 117.63(15) . . ? C23 C24 C25 109.05(15) . . ? C19 C20 C21 109.68(16) . . ? C24 C23 N6 116.47(14) . . ? C26 C25 C24 112.63(17) . . ? C22 C21 C20 112.91(17) . . ? C5 C6 C1 119.45(17) . . ? C18 C17 C16 113.34(16) . . ? C17 C16 C15 109.73(15) . . ? C4 C5 C6 121.08(17) . . ? C1 C2 C3 119.94(17) . . ? C5 C4 C3 119.52(19) . . ? C4 C3 C2 120.3(2) . . ? C7 N1 C1 129.22(14) . . ? C8 N3 N2 108.39(14) . . ? C7 N2 N3 122.89(15) . . ? O5 N5 O4 123.90(15) . . ? O5 N5 C13 118.23(14) . . ? O4 N5 C13 117.87(16) . . ? O2 N4 O3 123.97(16) . . ? O2 N4 C11 117.86(14) . . ? O3 N4 C11 118.16(15) . . ? C15 N6 C19 111.33(13) . . ? C15 N6 C27 111.28(13) . . ? C19 N6 C27 106.30(13) . . ? C15 N6 C23 106.49(13) . . ? C19 N6 C23 110.84(13) . . ? C27 N6 C23 110.67(12) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.40 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.346 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.067 data_ab-1 _database_code_depnum_ccdc_archive 'CCDC 899409' #TrackingRef 'all-cif-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H48 N6 O6 S' _chemical_formula_weight 620.81 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 11.9041(7) _cell_length_b 12.0508(7) _cell_length_c 13.7606(8) _cell_angle_alpha 71.458(4) _cell_angle_beta 71.925(4) _cell_angle_gamma 69.239(4) _cell_volume 1706.02(17) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.62 _cell_measurement_theta_max 21.22 _exptl_crystal_description Needle _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 668 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.955 _exptl_absorpt_correction_T_max 0.961 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21578 _diffrn_reflns_av_R_equivalents 0.0522 _diffrn_reflns_av_sigmaI/netI 0.0689 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 24.88 _reflns_number_total 5908 _reflns_number_gt 4872 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0879P)^2^+0.7070P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5508 _refine_ls_number_parameters 408 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.1372 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.2034 _refine_ls_wR_factor_gt 0.1714 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.018 _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 S1 S 0.70700(11) 0.71080(11) 0.46577(8) 0.0737(4) Uani 1 1 d . . . C9 C 0.5962(4) 1.0582(4) 0.0414(3) 0.0531(10) Uani 1 1 d . . . C13 C 0.6816(4) 1.0415(4) -0.1370(3) 0.0579(11) Uani 1 1 d . . . C10 C 0.5070(4) 1.1622(4) 0.0057(3) 0.0595(11) Uani 1 1 d . . . H10 H 0.4471 1.2050 0.0531 0.071 Uiso 1 1 calc R . . C11 C 0.5071(4) 1.2016(4) -0.0992(3) 0.0606(11) Uani 1 1 d . . . C14 C 0.6851(4) 0.9977(4) -0.0327(3) 0.0570(10) Uani 1 1 d . . . H14 H 0.7464 0.9281 -0.0114 0.068 Uiso 1 1 calc R . . C12 C 0.5929(4) 1.1424(4) -0.1733(3) 0.0635(12) Uani 1 1 d . . . H12 H 0.5908 1.1694 -0.2442 0.076 Uiso 1 1 calc R . . C8 C 0.5893(4) 1.0129(4) 0.1562(3) 0.0581(11) Uani 1 1 d . . . C7 C 0.7287(4) 0.7593(4) 0.3349(3) 0.0610(11) Uani 1 1 d . . . C1 C 0.9039(4) 0.5862(4) 0.2719(3) 0.0620(11) Uani 1 1 d . . . C6 C 0.9392(5) 0.5305(5) 0.1896(4) 0.0775(13) Uani 1 1 d . . . H6 H 0.9020 0.5676 0.1325 0.093 Uiso 1 1 calc R . . C2 C 0.9599(4) 0.5326(5) 0.3543(4) 0.0836(14) Uani 1 1 d . . . H2 H 0.9382 0.5703 0.4095 0.100 Uiso 1 1 calc R . . C3 C 1.0496(5) 0.4213(5) 0.3554(4) 0.0933(16) Uani 1 1 d . . . H3 H 1.0869 0.3841 0.4124 0.112 Uiso 1 1 calc R . . C5 C 1.0298(5) 0.4198(5) 0.1910(4) 0.0893(15) Uani 1 1 d . . . H5 H 1.0536 0.3825 0.1353 0.107 Uiso 1 1 calc R . . C4 C 1.0838(5) 0.3659(5) 0.2756(5) 0.0959(16) Uani 1 1 d . . . H4 H 1.1440 0.2912 0.2778 0.115 Uiso 1 1 calc R . . N2 N 0.6568(4) 0.8689(4) 0.2918(3) 0.0635(10) Uani 1 1 d . . . N3 N 0.6713(3) 0.9092(3) 0.1831(2) 0.0626(9) Uani 1 1 d . . . N6 N 0.7094(3) 0.2446(3) 0.3065(2) 0.0551(8) Uani 1 1 d . . . N1 N 0.8134(4) 0.7006(4) 0.2622(3) 0.0661(10) Uani 1 1 d . . . N5 N 0.7760(4) 0.9735(4) -0.2131(3) 0.0793(11) Uani 1 1 d . . . N4 N 0.4083(4) 1.3107(4) -0.1344(4) 0.0817(12) Uani 1 1 d . . . O1 O 0.5056(3) 1.0751(3) 0.2160(2) 0.0794(9) Uani 1 1 d . . . O3 O 0.4123(3) 1.3499(3) -0.2280(3) 0.0955(11) Uani 1 1 d . . . O4 O 0.7751(3) 1.0148(3) -0.3054(3) 0.1052(12) Uani 1 1 d . . . O2 O 0.3277(4) 1.3560(4) -0.0685(4) 0.1399(18) Uani 1 1 d . . . O5 O 0.8519(4) 0.8817(4) -0.1788(3) 0.1154(13) Uani 1 1 d . . . C15 C 0.5804(3) 0.2677(4) 0.2942(3) 0.0602(11) Uani 1 1 d . . . H15A H 0.5824 0.2083 0.2593 0.072 Uiso 1 1 calc R . . H15B H 0.5275 0.2531 0.3637 0.072 Uiso 1 1 calc R . . C16 C 0.5224(4) 0.3935(4) 0.2336(4) 0.0762(13) Uani 1 1 d . . . H16A H 0.5146 0.4539 0.2698 0.091 Uiso 1 1 calc R . . H16B H 0.5752 0.4106 0.1643 0.091 Uiso 1 1 calc R . . C17 C 0.3970(4) 0.4030(4) 0.2226(4) 0.0889(15) Uani 1 1 d . . . H17A H 0.3428 0.3918 0.2918 0.107 Uiso 1 1 calc R . . H17B H 0.4042 0.3380 0.1917 0.107 Uiso 1 1 calc R . . C18 C 0.3403(5) 0.5248(5) 0.1548(5) 0.122(2) Uani 1 1 d . . . H18A H 0.3370 0.5896 0.1829 0.183 Uiso 1 1 calc R . . H18B H 0.2584 0.5290 0.1543 0.183 Uiso 1 1 calc R . . H18C H 0.3896 0.5329 0.0843 0.183 Uiso 1 1 calc R . . C19 C 0.7105(4) 0.3255(4) 0.3708(3) 0.0630(11) Uani 1 1 d . . . H19A H 0.7949 0.3094 0.3749 0.076 Uiso 1 1 calc R . . H19B H 0.6836 0.4098 0.3332 0.076 Uiso 1 1 calc R . . C20 C 0.6318(4) 0.3113(4) 0.4811(3) 0.0692(12) Uani 1 1 d . . . H20A H 0.6555 0.2268 0.5193 0.083 Uiso 1 1 calc R . . H20B H 0.5460 0.3328 0.4784 0.083 Uiso 1 1 calc R . . C21 C 0.6466(4) 0.3923(4) 0.5382(4) 0.0804(13) Uani 1 1 d . . . H21A H 0.6404 0.4731 0.4922 0.097 Uiso 1 1 calc R . . H21B H 0.5791 0.3998 0.5995 0.097 Uiso 1 1 calc R . . C22 C 0.7659(5) 0.3471(5) 0.5732(4) 0.0978(16) Uani 1 1 d . . . H22A H 0.7728 0.2673 0.6192 0.147 Uiso 1 1 calc R . . H22B H 0.7678 0.4021 0.6097 0.147 Uiso 1 1 calc R . . H22C H 0.8335 0.3430 0.5129 0.147 Uiso 1 1 calc R . . C23 C 0.7513(4) 0.1110(4) 0.3607(3) 0.0604(11) Uani 1 1 d . . . H23A H 0.6883 0.0940 0.4232 0.072 Uiso 1 1 calc R . . H23B H 0.7568 0.0625 0.3142 0.072 Uiso 1 1 calc R . . C24 C 0.8729(4) 0.0688(4) 0.3927(4) 0.0734(13) Uani 1 1 d . . . H24A H 0.8630 0.1003 0.4524 0.088 Uiso 1 1 calc R . . H24B H 0.9333 0.1007 0.3351 0.088 Uiso 1 1 calc R . . C25 C 0.9190(5) -0.0709(4) 0.4219(4) 0.0869(15) Uani 1 1 d . . . H25A H 0.9847 -0.0956 0.4587 0.104 Uiso 1 1 calc R . . H25B H 0.8523 -0.1027 0.4695 0.104 Uiso 1 1 calc R . . C26 C 0.9660(5) -0.1257(5) 0.3275(4) 0.1012(17) Uani 1 1 d . . . H26A H 0.9014 -0.1014 0.2906 0.152 Uiso 1 1 calc R . . H26B H 0.9917 -0.2131 0.3501 0.152 Uiso 1 1 calc R . . H26C H 1.0346 -0.0976 0.2816 0.152 Uiso 1 1 calc R . . C27 C 0.7954(4) 0.2730(4) 0.2013(3) 0.0691(12) Uani 1 1 d . . . H27A H 0.8771 0.2538 0.2131 0.083 Uiso 1 1 calc R . . H27B H 0.7691 0.3602 0.1718 0.083 Uiso 1 1 calc R . . C28 C 0.8050(4) 0.2076(4) 0.1202(3) 0.0811(14) Uani 1 1 d . . . H28A H 0.8316 0.1200 0.1479 0.097 Uiso 1 1 calc R . . H28B H 0.7248 0.2282 0.1049 0.097 Uiso 1 1 calc R . . C29 C 0.8963(5) 0.2440(5) 0.0202(4) 0.0988(17) Uani 1 1 d . . . H29A H 0.8701 0.3319 -0.0057 0.119 Uiso 1 1 calc R . . H29B H 0.9762 0.2225 0.0363 0.119 Uiso 1 1 calc R . . C30 C 0.9091(6) 0.1844(6) -0.0644(4) 0.126(2) Uani 1 1 d . . . H30A H 0.9307 0.0974 -0.0380 0.188 Uiso 1 1 calc R . . H30B H 0.9725 0.2058 -0.1235 0.188 Uiso 1 1 calc R . . H30C H 0.8324 0.2118 -0.0858 0.188 Uiso 1 1 calc R . . O6 O 0.4158(4) 0.0211(4) 0.4285(3) 0.1148(13) Uani 1 1 d D . . H1 H 0.804(4) 0.733(4) 0.198(3) 0.077(14) Uiso 1 1 d . . . H2A H 0.598(4) 0.909(4) 0.337(3) 0.077(16) Uiso 1 1 d . . . H6A H 0.402(8) 0.072(6) 0.471(5) 0.27(4) Uiso 1 1 d D . . H6B H 0.428(6) 0.062(5) 0.357(2) 0.17(3) Uiso 1 1 d 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 0.0747(8) 0.0835(9) 0.0558(7) -0.0042(6) -0.0177(6) -0.0221(7) C9 0.061(3) 0.051(3) 0.054(2) -0.009(2) -0.016(2) -0.025(2) C13 0.065(3) 0.061(3) 0.052(2) -0.014(2) -0.005(2) -0.029(2) C10 0.069(3) 0.051(3) 0.060(3) -0.013(2) -0.015(2) -0.019(2) C11 0.061(3) 0.053(3) 0.066(3) 0.000(2) -0.022(2) -0.020(2) C14 0.057(3) 0.053(2) 0.065(3) -0.013(2) -0.014(2) -0.020(2) C12 0.076(3) 0.069(3) 0.053(2) 0.000(2) -0.020(3) -0.036(3) C8 0.071(3) 0.052(3) 0.057(3) -0.015(2) -0.016(2) -0.022(3) C7 0.063(3) 0.067(3) 0.062(3) -0.010(2) -0.021(2) -0.028(3) C1 0.060(3) 0.061(3) 0.067(3) -0.008(2) -0.020(2) -0.020(3) C6 0.076(3) 0.086(4) 0.081(3) -0.025(3) -0.019(3) -0.028(3) C2 0.069(3) 0.103(4) 0.076(3) -0.030(3) -0.022(3) -0.009(3) C3 0.075(4) 0.102(4) 0.093(4) -0.024(3) -0.028(3) -0.004(3) C5 0.076(4) 0.087(4) 0.114(4) -0.044(3) -0.015(3) -0.020(3) C4 0.079(4) 0.081(4) 0.126(5) -0.029(4) -0.027(4) -0.013(3) N2 0.068(3) 0.067(3) 0.053(2) -0.012(2) -0.017(2) -0.014(2) N3 0.075(3) 0.068(2) 0.0457(19) -0.0055(17) -0.0195(18) -0.023(2) N6 0.048(2) 0.056(2) 0.061(2) -0.0105(17) -0.0090(16) -0.0204(17) N1 0.074(3) 0.071(3) 0.053(2) -0.010(2) -0.022(2) -0.017(2) N5 0.092(3) 0.084(3) 0.063(3) -0.018(2) -0.005(2) -0.035(3) N4 0.081(3) 0.074(3) 0.087(3) 0.005(3) -0.037(3) -0.024(3) O1 0.102(3) 0.068(2) 0.0609(18) -0.0221(16) -0.0152(18) -0.0127(19) O3 0.110(3) 0.083(2) 0.093(2) 0.0180(19) -0.052(2) -0.036(2) O4 0.115(3) 0.139(3) 0.057(2) -0.028(2) -0.0007(19) -0.043(2) O2 0.110(3) 0.140(4) 0.110(3) -0.025(3) -0.033(3) 0.040(3) O5 0.126(3) 0.095(3) 0.087(3) -0.027(2) -0.005(2) 0.002(3) C15 0.051(3) 0.070(3) 0.066(3) -0.017(2) -0.012(2) -0.024(2) C16 0.073(3) 0.068(3) 0.091(3) -0.013(3) -0.030(3) -0.019(3) C17 0.074(3) 0.081(3) 0.115(4) -0.010(3) -0.045(3) -0.017(3) C18 0.107(4) 0.118(5) 0.132(5) 0.004(4) -0.065(4) -0.017(4) C19 0.062(3) 0.059(3) 0.074(3) -0.013(2) -0.019(2) -0.023(2) C20 0.066(3) 0.073(3) 0.074(3) -0.030(2) -0.007(2) -0.021(2) C21 0.078(3) 0.076(3) 0.085(3) -0.025(3) -0.022(3) -0.010(3) C22 0.110(4) 0.102(4) 0.095(4) -0.028(3) -0.036(3) -0.031(3) C23 0.058(3) 0.059(3) 0.063(2) -0.014(2) -0.012(2) -0.016(2) C24 0.072(3) 0.070(3) 0.081(3) -0.022(2) -0.025(3) -0.013(3) C25 0.080(3) 0.079(4) 0.099(4) -0.019(3) -0.039(3) -0.005(3) C26 0.084(4) 0.091(4) 0.143(5) -0.048(4) -0.033(4) -0.018(3) C27 0.062(3) 0.082(3) 0.063(3) -0.012(2) -0.004(2) -0.032(2) C28 0.083(3) 0.086(3) 0.068(3) -0.020(3) 0.000(3) -0.029(3) C29 0.098(4) 0.134(5) 0.068(3) -0.020(3) -0.004(3) -0.052(4) C30 0.145(6) 0.146(5) 0.075(4) -0.034(4) -0.002(4) -0.042(4) O6 0.130(3) 0.122(3) 0.073(3) -0.008(3) 0.004(2) -0.048(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 S1 C7 1.673(4) . ? C9 C10 1.388(5) . ? C9 C14 1.395(5) . ? C9 C8 1.485(5) . ? C13 C12 1.369(5) . ? C13 C14 1.371(5) . ? C13 N5 1.481(6) . ? C10 C11 1.369(5) . ? C11 C12 1.376(6) . ? C11 N4 1.482(6) . ? C8 O1 1.259(5) . ? C8 N3 1.310(5) . ? C7 N2 1.357(5) . ? C7 N1 1.356(5) . ? C1 C2 1.358(6) . ? C1 C6 1.378(6) . ? C1 N1 1.413(5) . ? C6 C5 1.386(6) . ? C2 C3 1.387(6) . ? C3 C4 1.346(7) . ? C5 C4 1.369(7) . ? N2 N3 1.393(4) . ? N6 C27 1.507(5) . ? N6 C15 1.515(4) . ? N6 C23 1.515(5) . ? N6 C19 1.516(5) . ? N5 O4 1.210(4) . ? N5 O5 1.220(5) . ? N4 O2 1.202(5) . ? N4 O3 1.216(4) . ? C15 C16 1.511(5) . ? C16 C17 1.508(6) . ? C17 C18 1.516(6) . ? C19 C20 1.509(5) . ? C20 C21 1.516(6) . ? C21 C22 1.501(6) . ? C23 C24 1.509(5) . ? C24 C25 1.532(6) . ? C25 C26 1.507(6) . ? C27 C28 1.516(6) . ? C28 C29 1.514(6) . ? C29 C30 1.496(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 C10 C9 C14 118.0(4) . . ? C10 C9 C8 118.9(4) . . ? C14 C9 C8 123.0(4) . . ? C12 C13 C14 123.1(4) . . ? C12 C13 N5 118.7(4) . . ? C14 C13 N5 118.2(4) . . ? C11 C10 C9 120.0(4) . . ? C10 C11 C12 122.9(4) . . ? C10 C11 N4 118.7(4) . . ? C12 C11 N4 118.5(4) . . ? C13 C14 C9 119.7(4) . . ? C13 C12 C11 116.3(4) . . ? O1 C8 N3 127.7(4) . . ? O1 C8 C9 117.7(4) . . ? N3 C8 C9 114.6(4) . . ? N2 C7 N1 113.2(4) . . ? N2 C7 S1 119.7(4) . . ? N1 C7 S1 127.1(4) . . ? C2 C1 C6 119.5(5) . . ? C2 C1 N1 123.9(4) . . ? C6 C1 N1 116.6(4) . . ? C1 C6 C5 120.6(5) . . ? C1 C2 C3 119.5(5) . . ? C4 C3 C2 121.3(5) . . ? C4 C5 C6 119.2(5) . . ? C3 C4 C5 120.0(5) . . ? C7 N2 N3 120.5(4) . . ? C8 N3 N2 112.0(4) . . ? C27 N6 C15 111.2(3) . . ? C27 N6 C23 110.8(3) . . ? C15 N6 C23 106.3(3) . . ? C27 N6 C19 106.7(3) . . ? C15 N6 C19 111.0(3) . . ? C23 N6 C19 110.9(3) . . ? C7 N1 C1 131.9(4) . . ? O4 N5 O5 124.4(5) . . ? O4 N5 C13 117.9(5) . . ? O5 N5 C13 117.7(4) . . ? O2 N4 O3 123.1(5) . . ? O2 N4 C11 118.2(4) . . ? O3 N4 C11 118.7(5) . . ? C16 C15 N6 116.1(3) . . ? C17 C16 C15 110.9(4) . . ? C16 C17 C18 112.4(4) . . ? C20 C19 N6 116.3(3) . . ? C19 C20 C21 110.7(4) . . ? C22 C21 C20 114.4(4) . . ? C24 C23 N6 116.2(3) . . ? C23 C24 C25 110.8(4) . . ? C26 C25 C24 112.8(4) . . ? N6 C27 C28 116.7(3) . . ? C29 C28 C27 110.2(4) . . ? C30 C29 C28 113.2(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.88 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.227 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.046 data_salt3 _database_code_depnum_ccdc_archive 'CCDC 899410' #TrackingRef 'all-cif-final.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum ' C68 H98 N12 O11 S2' _chemical_formula_weight 1323.72 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 15.6959(6) _cell_length_b 16.0526(7) _cell_length_c 17.2487(8) _cell_angle_alpha 111.240(2) _cell_angle_beta 111.383(2) _cell_angle_gamma 93.571(2) _cell_volume 3676.1(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.18 _cell_measurement_theta_max 21.27 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.196 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1420 _exptl_absorpt_coefficient_mu 0.136 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.957 _exptl_absorpt_correction_T_max 0.963 _exptl_absorpt_process_details SADBAS _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 41515 _diffrn_reflns_av_R_equivalents 0.0370 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 24.77 _reflns_number_total 12518 _reflns_number_gt 7489 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.9679P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12318 _refine_ls_number_parameters 870 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.1103 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.2174 _refine_ls_wR_factor_gt 0.1891 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.185 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S2 S 0.96798(6) 0.74181(6) 0.46159(7) 0.0659(3) Uani 1 1 d . . . C9 C 0.4047(4) 0.9563(3) 0.1158(3) 0.0945(13) Uani 1 1 d . . . C1 C 0.3091(4) 0.9370(3) 0.1043(3) 0.0887(12) Uani 1 1 d . . . C4 C 0.3753(9) 1.0951(5) 0.0939(6) 0.177(4) Uani 1 1 d . . . H4 H 0.3958 1.1477 0.0888 0.212 Uiso 1 1 calc R . . C2 C 0.2501(5) 0.9943(3) 0.0889(4) 0.1234(18) Uani 1 1 d . . . H2 H 0.1882 0.9805 0.0807 0.148 Uiso 1 1 calc R . . C10 C 0.4372(6) 1.0392(4) 0.1096(4) 0.132(2) Uani 1 1 d . . . C3 C 0.2878(8) 1.0771(5) 0.0859(5) 0.160(3) Uani 1 1 d . . . H3 H 0.2502 1.1185 0.0782 0.193 Uiso 1 1 calc R . . C8 C 0.4688(4) 0.9017(4) 0.1319(3) 0.1045(14) Uani 1 1 d . . . H8 H 0.4498 0.8493 0.1382 0.125 Uiso 1 1 calc R . . C6 C 0.5886(6) 0.9993(6) 0.1318(5) 0.165(3) Uani 1 1 d . . . H6 H 0.6492 1.0122 0.1361 0.198 Uiso 1 1 calc R . . C7 C 0.5573(4) 0.9209(5) 0.1391(4) 0.137(2) Uani 1 1 d . . . H7 H 0.5970 0.8816 0.1490 0.164 Uiso 1 1 calc R . . C5 C 0.5309(7) 1.0570(5) 0.1183(5) 0.156(3) Uani 1 1 d . . . H5 H 0.5533 1.1099 0.1147 0.188 Uiso 1 1 calc R . . C13 C 0.3474(2) 0.5677(2) 0.1119(2) 0.0626(8) Uani 1 1 d . . . C12 C 0.2662(2) 0.6126(2) 0.1083(2) 0.0626(8) Uani 1 1 d . . . C18 C 0.4287(2) 0.6091(2) 0.1119(2) 0.0652(9) Uani 1 1 d . . . H18 H 0.4333 0.6659 0.1092 0.078 Uiso 1 1 calc R . . C14 C 0.3433(3) 0.4833(2) 0.1160(3) 0.0768(10) Uani 1 1 d . . . H14 H 0.2896 0.4540 0.1149 0.092 Uiso 1 1 calc R . . C17 C 0.5015(2) 0.5651(2) 0.1161(2) 0.0689(9) Uani 1 1 d . . . C16 C 0.4989(3) 0.4811(3) 0.1212(3) 0.0842(11) Uani 1 1 d . . . H16 H 0.5487 0.4521 0.1242 0.101 Uiso 1 1 calc R . . C11 C 0.2043(3) 0.8190(3) 0.1147(3) 0.0773(10) Uani 1 1 d . . . C15 C 0.4184(3) 0.4428(3) 0.1216(3) 0.0889(12) Uani 1 1 d . . . N3 N 0.28288(19) 0.69650(19) 0.1150(2) 0.0664(7) Uani 1 1 d . . . N2 N 0.2051(2) 0.7351(2) 0.1131(2) 0.0757(9) Uani 1 1 d . . . N1 N 0.2807(3) 0.8551(2) 0.1088(2) 0.0831(9) Uani 1 1 d . . . N5 N 0.5849(2) 0.6081(3) 0.1133(2) 0.0873(10) Uani 1 1 d . . . N4 N 0.4136(4) 0.3542(3) 0.1285(4) 0.148(2) Uani 1 1 d . . . O1 O 0.19101(17) 0.56840(17) 0.09892(19) 0.0811(7) Uani 1 1 d . . . O4 O 0.5842(2) 0.6777(2) 0.1023(3) 0.1169(11) Uani 1 1 d . . . O5 O 0.6511(2) 0.5706(2) 0.1218(3) 0.1219(12) Uani 1 1 d . . . O2 O 0.3399(3) 0.3164(3) 0.1213(5) 0.192(2) Uani 1 1 d . . . O3 O 0.4842(3) 0.3241(3) 0.1423(5) 0.215(3) Uani 1 1 d . . . S1 S 0.11408(9) 0.86581(8) 0.12474(11) 0.1223(5) Uani 1 1 d . . . C19 C 0.7368(2) 0.7097(2) 0.3596(2) 0.0570(8) Uani 1 1 d . . . C27 C 0.6444(2) 0.6958(2) 0.3559(2) 0.0597(8) Uani 1 1 d . . . C28 C 0.5914(2) 0.7635(2) 0.3449(2) 0.0681(9) Uani 1 1 d . . . C21 C 0.7180(3) 0.8487(3) 0.3391(3) 0.0823(11) Uani 1 1 d . . . H21 H 0.7427 0.8993 0.3334 0.099 Uiso 1 1 calc R . . C23 C 0.5002(3) 0.7511(3) 0.3421(3) 0.0853(12) Uani 1 1 d . . . H23 H 0.4649 0.7942 0.3344 0.102 Uiso 1 1 calc R . . C20 C 0.7718(3) 0.7834(2) 0.3499(2) 0.0677(9) Uani 1 1 d . . . H20 H 0.8313 0.7906 0.3505 0.081 Uiso 1 1 calc R . . C26 C 0.6025(2) 0.6215(2) 0.3634(3) 0.0719(10) Uani 1 1 d . . . H26 H 0.6358 0.5768 0.3702 0.086 Uiso 1 1 calc R . . C22 C 0.6309(3) 0.8389(3) 0.3369(3) 0.0797(11) Uani 1 1 d . . . H22 H 0.5967 0.8830 0.3300 0.096 Uiso 1 1 calc R . . C25 C 0.5151(3) 0.6120(3) 0.3610(3) 0.0906(12) Uani 1 1 d . . . H25 H 0.4896 0.5618 0.3666 0.109 Uiso 1 1 calc R . . C24 C 0.4631(3) 0.6784(3) 0.3501(3) 0.0957(13) Uani 1 1 d . . . H24 H 0.4031 0.6720 0.3484 0.115 Uiso 1 1 calc R . . N6 N 0.7880(2) 0.64270(19) 0.3727(2) 0.0617(7) Uani 1 1 d . . . N7 N 0.8987(2) 0.57376(17) 0.4305(2) 0.0561(7) Uani 1 1 d . . . N8 N 0.82426(18) 0.50449(17) 0.40883(19) 0.0597(7) Uani 1 1 d . . . C31 C 0.7707(2) 0.3535(2) 0.3864(2) 0.0594(8) Uani 1 1 d . . . C32 C 0.7895(2) 0.2695(2) 0.3843(2) 0.0656(9) Uani 1 1 d . . . H32 H 0.8488 0.2582 0.3926 0.079 Uiso 1 1 calc R . . C36 C 0.6817(2) 0.3674(2) 0.3730(3) 0.0762(10) Uani 1 1 d . . . H36 H 0.6678 0.4230 0.3732 0.091 Uiso 1 1 calc R . . C33 C 0.7174(3) 0.2029(2) 0.3696(3) 0.0757(10) Uani 1 1 d . . . C35 C 0.6137(3) 0.2994(3) 0.3594(3) 0.0891(12) Uani 1 1 d . . . C34 C 0.6304(3) 0.2158(2) 0.3583(3) 0.0864(12) Uani 1 1 d . . . H34 H 0.5839 0.1706 0.3501 0.104 Uiso 1 1 calc R . . C30 C 0.8489(2) 0.4270(2) 0.4051(2) 0.0547(8) Uani 1 1 d . . . O6 O 0.92794(15) 0.40905(14) 0.41574(17) 0.0696(6) Uani 1 1 d . . . O8 O 0.6829(3) 0.0654(2) 0.3767(3) 0.1474(15) Uani 1 1 d . . . O7 O 0.8078(3) 0.0945(2) 0.3588(3) 0.1428(16) Uani 1 1 d . . . O10 O 0.5074(3) 0.3924(3) 0.3543(5) 0.197(3) Uani 1 1 d . . . O9 O 0.4594(3) 0.2572(3) 0.3340(4) 0.182(2) Uani 1 1 d . . . N9 N 0.7382(3) 0.1144(2) 0.3691(3) 0.1040(12) Uani 1 1 d . . . N10 N 0.5204(3) 0.3187(3) 0.3490(4) 0.1358(18) Uani 1 1 d . . . C29 C 0.8805(2) 0.6504(2) 0.4199(2) 0.0514(7) Uani 1 1 d . . . C37 C 0.1563(3) 0.1232(3) 0.4013(3) 0.0868(12) Uani 1 1 d . . . H37A H 0.1132 0.1569 0.4206 0.104 Uiso 1 1 calc R . . H37B H 0.2125 0.1354 0.4557 0.104 Uiso 1 1 calc R . . C39 C 0.1045(6) -0.0023(5) 0.4321(5) 0.177(3) Uani 1 1 d D . . H39A H 0.1655 -0.0073 0.4700 0.212 Uiso 1 1 calc R . . H39B H 0.0846 0.0456 0.4706 0.212 Uiso 1 1 calc R . . C38 C 0.1121(4) 0.0228(4) 0.3569(4) 0.1211(17) Uani 1 1 d . . . H38A H 0.1507 -0.0124 0.3310 0.145 Uiso 1 1 calc R . . H38B H 0.0504 0.0101 0.3084 0.145 Uiso 1 1 calc R . . C40 C 0.0368(8) -0.0893(7) 0.3909(7) 0.298(7) Uani 1 1 d D . . H40A H -0.0257 -0.0797 0.3685 0.447 Uiso 1 1 calc R . . H40B H 0.0447 -0.1132 0.4361 0.447 Uiso 1 1 calc R . . H40C H 0.0469 -0.1322 0.3411 0.447 Uiso 1 1 calc R . . C41 C 0.0978(3) 0.1378(3) 0.2530(3) 0.0837(11) Uani 1 1 d . . . H41A H 0.1173 0.1625 0.2170 0.100 Uiso 1 1 calc R . . H41B H 0.0782 0.0717 0.2190 0.100 Uiso 1 1 calc R . . C42 C 0.0144(3) 0.1740(4) 0.2627(4) 0.1124(15) Uani 1 1 d . . . H42A H 0.0295 0.2404 0.2868 0.135 Uiso 1 1 calc R . . H42B H -0.0008 0.1570 0.3055 0.135 Uiso 1 1 calc R . . C44 C -0.1534(6) 0.1557(8) 0.1698(6) 0.244(5) Uani 1 1 d . . . H44A H -0.1712 0.1321 0.2068 0.366 Uiso 1 1 calc R . . H44B H -0.2011 0.1284 0.1082 0.366 Uiso 1 1 calc R . . H44C H -0.1465 0.2210 0.1941 0.366 Uiso 1 1 calc R . . C43 C -0.0701(4) 0.1351(5) 0.1701(4) 0.147(2) Uani 1 1 d . . . H43A H -0.0550 0.1568 0.1299 0.176 Uiso 1 1 calc R . . H43B H -0.0791 0.0689 0.1439 0.176 Uiso 1 1 calc R . . C45 C 0.2194(3) 0.2626(3) 0.3979(3) 0.0785(10) Uani 1 1 d . . . H45A H 0.1732 0.2871 0.4191 0.094 Uiso 1 1 calc R . . H45B H 0.2757 0.2726 0.4515 0.094 Uiso 1 1 calc R . . C46 C 0.2426(3) 0.3171(3) 0.3504(3) 0.0826(11) Uani 1 1 d . . . H46A H 0.1850 0.3198 0.3053 0.099 Uiso 1 1 calc R . . H46B H 0.2795 0.2870 0.3188 0.099 Uiso 1 1 calc R . . C47 C 0.2973(3) 0.4137(3) 0.4189(3) 0.0976(13) Uani 1 1 d . . . H47A H 0.2659 0.4388 0.4585 0.117 Uiso 1 1 calc R . . H47B H 0.3594 0.4110 0.4568 0.117 Uiso 1 1 calc R . . C48 C 0.3071(4) 0.4769(4) 0.3754(4) 0.1218(17) Uani 1 1 d . . . H48A H 0.3294 0.4485 0.3294 0.183 Uiso 1 1 calc R . . H48B H 0.3511 0.5331 0.4211 0.183 Uiso 1 1 calc R . . H48C H 0.2472 0.4897 0.3478 0.183 Uiso 1 1 calc R . . C49 C 0.2555(3) 0.1148(3) 0.3158(3) 0.0792(10) Uani 1 1 d . . . H49A H 0.2710 0.1410 0.2787 0.095 Uiso 1 1 calc R . . H49B H 0.2280 0.0500 0.2780 0.095 Uiso 1 1 calc R . . C50 C 0.3457(3) 0.1242(4) 0.3945(4) 0.1150(17) Uani 1 1 d . . . H50A H 0.3802 0.1877 0.4279 0.138 Uiso 1 1 calc R . . H50B H 0.3321 0.1043 0.4363 0.138 Uiso 1 1 calc R . . C51 C 0.4029(4) 0.0649(5) 0.3541(5) 0.140(2) Uani 1 1 d D . . H51A H 0.3600 0.0142 0.2978 0.168 Uiso 1 1 calc R . . H51B H 0.4403 0.1008 0.3383 0.168 Uiso 1 1 calc R . . C52 C 0.4655(11) 0.0274(11) 0.4124(9) 0.420(13) Uani 1 1 d D . . H52A H 0.4839 0.0676 0.4755 0.630 Uiso 1 1 calc R . . H52B H 0.5203 0.0220 0.4001 0.630 Uiso 1 1 calc R . . H52C H 0.4336 -0.0320 0.4001 0.630 Uiso 1 1 calc R . . C53 C 0.8965(2) 0.5059(3) 0.2040(2) 0.0697(9) Uani 1 1 d . . . H53A H 0.9316 0.4776 0.2427 0.084 Uiso 1 1 calc R . . H53B H 0.8731 0.5524 0.2399 0.084 Uiso 1 1 calc R . . C54 C 0.8133(3) 0.4339(3) 0.1253(3) 0.0793(10) Uani 1 1 d . . . H54A H 0.8346 0.3866 0.0878 0.095 Uiso 1 1 calc R . . H54B H 0.7744 0.4612 0.0875 0.095 Uiso 1 1 calc R . . C55 C 0.7564(3) 0.3919(3) 0.1629(3) 0.0968(13) Uani 1 1 d . . . H55A H 0.7986 0.3731 0.2074 0.116 Uiso 1 1 calc R . . H55B H 0.7303 0.4389 0.1948 0.116 Uiso 1 1 calc R . . C56 C 0.6779(4) 0.3111(4) 0.0924(4) 0.1294(18) Uani 1 1 d . . . H56A H 0.6364 0.3282 0.0469 0.194 Uiso 1 1 calc R . . H56B H 0.6437 0.2913 0.1212 0.194 Uiso 1 1 calc R . . H56C H 0.7032 0.2619 0.0639 0.194 Uiso 1 1 calc R . . C59 C 1.0686(3) 0.3522(3) 0.0764(3) 0.0782(10) Uani 1 1 d . . . H59A H 1.0129 0.3236 0.0192 0.094 Uiso 1 1 calc R . . H59B H 1.1127 0.3883 0.0670 0.094 Uiso 1 1 calc R . . C57 C 0.9976(2) 0.4850(2) 0.1174(2) 0.0667(9) Uani 1 1 d . . . H57A H 0.9443 0.4521 0.0588 0.080 Uiso 1 1 calc R . . H57B H 1.0426 0.5192 0.1074 0.080 Uiso 1 1 calc R . . C58 C 1.0418(3) 0.4156(3) 0.1477(3) 0.0833(11) Uani 1 1 d . . . H58A H 0.9980 0.3805 0.1583 0.100 Uiso 1 1 calc R . . H58B H 1.0973 0.4468 0.2048 0.100 Uiso 1 1 calc R . . C60 C 1.1116(4) 0.2781(3) 0.0984(3) 0.1061(15) Uani 1 1 d . . . H60A H 1.1709 0.3053 0.1507 0.159 Uiso 1 1 calc R . . H60B H 1.1211 0.2376 0.0470 0.159 Uiso 1 1 calc R . . H60C H 1.0704 0.2441 0.1116 0.159 Uiso 1 1 calc R . . C61 C 1.0446(2) 0.6131(3) 0.2722(2) 0.0715(10) Uani 1 1 d . . . H61A H 1.0188 0.6504 0.3125 0.086 Uiso 1 1 calc R . . H61B H 1.0750 0.5733 0.2990 0.086 Uiso 1 1 calc R . . C62 C 1.1187(3) 0.6759(3) 0.2701(3) 0.0824(11) Uani 1 1 d . . . H62A H 1.0906 0.7194 0.2477 0.099 Uiso 1 1 calc R . . H62B H 1.1441 0.6401 0.2286 0.099 Uiso 1 1 calc R . . C63 C 1.1971(3) 0.7273(3) 0.3646(3) 0.1071(15) Uani 1 1 d . . . H63A H 1.2306 0.6844 0.3836 0.129 Uiso 1 1 calc R . . H63B H 1.1707 0.7562 0.4078 0.129 Uiso 1 1 calc R . . C64 C 1.2653(3) 0.7999(4) 0.3661(4) 0.1307(19) Uani 1 1 d . . . H64A H 1.2976 0.7708 0.3296 0.196 Uiso 1 1 calc R . . H64B H 1.3101 0.8360 0.4280 0.196 Uiso 1 1 calc R . . H64C H 1.2314 0.8390 0.3419 0.196 Uiso 1 1 calc R . . C65 C 0.9171(3) 0.6093(3) 0.1300(2) 0.0703(9) Uani 1 1 d . . . H65A H 0.9624 0.6355 0.1143 0.084 Uiso 1 1 calc R . . H65B H 0.8659 0.5674 0.0730 0.084 Uiso 1 1 calc R . . C66 C 0.8785(3) 0.6860(3) 0.1777(3) 0.0759(10) Uani 1 1 d . . . H66A H 0.9264 0.7258 0.2379 0.091 Uiso 1 1 calc R . . H66B H 0.8255 0.6610 0.1851 0.091 Uiso 1 1 calc R . . C67 C 0.8474(4) 0.7404(4) 0.1196(4) 0.1134(16) Uani 1 1 d . . . H67A H 0.9010 0.7627 0.1115 0.136 Uiso 1 1 calc R . . H67B H 0.8006 0.6988 0.0596 0.136 Uiso 1 1 calc R . . C68 C 0.8075(4) 0.8207(4) 0.1570(4) 0.135(2) Uani 1 1 d . . . H68A H 0.7520 0.7994 0.1620 0.202 Uiso 1 1 calc R . . H68B H 0.7918 0.8510 0.1165 0.202 Uiso 1 1 calc R . . H68C H 0.8531 0.8629 0.2163 0.202 Uiso 1 1 calc R . . N12 N 0.96392(19) 0.55347(19) 0.18112(18) 0.0631(7) Uani 1 1 d . . . N11 N 0.1821(2) 0.1593(2) 0.3418(2) 0.0731(8) Uani 1 1 d . . . O11 O 0.0672(3) 0.4424(3) 0.3655(3) 0.1191(12) Uani 1 1 d D . . H2N H 0.161(3) 0.707(3) 0.123(3) 0.091(14) Uiso 1 1 d . . . H1N H 0.326(3) 0.822(3) 0.115(3) 0.110(15) Uiso 1 1 d . . . H7N H 0.959(2) 0.577(2) 0.465(2) 0.069(10) Uiso 1 1 d . . . H6N H 0.7525(19) 0.594(2) 0.3620(19) 0.045(8) Uiso 1 1 d . . . H11A H 0.014(3) 0.419(4) 0.370(4) 0.15(2) Uiso 1 1 d D . . H11B H 0.115(4) 0.476(5) 0.420(3) 0.23(4) Uiso 1 1 d 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 S2 0.0713(5) 0.0541(5) 0.0897(7) 0.0373(5) 0.0432(5) 0.0216(4) C9 0.139(4) 0.065(3) 0.068(3) 0.022(2) 0.040(3) -0.001(3) C1 0.142(4) 0.054(2) 0.071(3) 0.026(2) 0.044(3) 0.031(2) C4 0.335(13) 0.081(4) 0.164(7) 0.069(4) 0.137(9) 0.061(7) C2 0.201(6) 0.089(3) 0.113(4) 0.056(3) 0.079(4) 0.074(4) C10 0.215(7) 0.074(3) 0.096(4) 0.031(3) 0.062(4) -0.005(4) C3 0.295(11) 0.107(5) 0.150(6) 0.082(5) 0.130(8) 0.106(7) C8 0.103(3) 0.097(3) 0.103(4) 0.046(3) 0.031(3) 0.002(3) C6 0.150(6) 0.172(7) 0.140(6) 0.059(6) 0.042(5) -0.037(6) C7 0.114(4) 0.143(5) 0.141(5) 0.068(4) 0.038(4) -0.022(4) C5 0.210(9) 0.115(5) 0.125(5) 0.043(4) 0.070(6) -0.046(5) C13 0.066(2) 0.0538(19) 0.057(2) 0.0178(16) 0.0189(16) 0.0088(16) C12 0.069(2) 0.056(2) 0.057(2) 0.0189(17) 0.0249(16) 0.0122(17) C18 0.070(2) 0.0551(19) 0.061(2) 0.0184(17) 0.0232(17) 0.0110(17) C14 0.075(2) 0.063(2) 0.092(3) 0.036(2) 0.031(2) 0.0119(18) C17 0.058(2) 0.065(2) 0.065(2) 0.0159(18) 0.0186(16) 0.0060(17) C16 0.073(2) 0.074(3) 0.097(3) 0.036(2) 0.025(2) 0.026(2) C11 0.081(3) 0.059(2) 0.068(2) 0.0098(19) 0.022(2) 0.0207(19) C15 0.083(3) 0.071(2) 0.116(4) 0.050(3) 0.034(2) 0.024(2) N3 0.0665(17) 0.0582(17) 0.075(2) 0.0273(15) 0.0299(15) 0.0179(14) N2 0.077(2) 0.0586(18) 0.091(2) 0.0235(17) 0.0408(18) 0.0206(16) N1 0.097(3) 0.064(2) 0.094(3) 0.0338(19) 0.042(2) 0.0287(19) N5 0.073(2) 0.075(2) 0.093(3) 0.018(2) 0.0311(18) 0.0082(19) N4 0.113(3) 0.108(3) 0.276(7) 0.127(4) 0.087(4) 0.054(3) O1 0.0756(16) 0.0645(15) 0.103(2) 0.0276(14) 0.0451(14) 0.0108(13) O4 0.096(2) 0.096(2) 0.178(4) 0.063(2) 0.072(2) 0.0166(18) O5 0.0748(18) 0.107(2) 0.176(4) 0.044(2) 0.055(2) 0.0299(18) O2 0.142(3) 0.130(3) 0.378(8) 0.170(5) 0.118(4) 0.053(3) O3 0.164(4) 0.166(4) 0.439(10) 0.211(6) 0.160(5) 0.103(3) S1 0.0922(8) 0.0752(7) 0.1585(13) 0.0108(8) 0.0441(8) 0.0334(6) C19 0.071(2) 0.0498(18) 0.052(2) 0.0232(15) 0.0232(16) 0.0267(15) C27 0.068(2) 0.0494(18) 0.054(2) 0.0208(16) 0.0159(15) 0.0223(15) C28 0.072(2) 0.063(2) 0.060(2) 0.0213(18) 0.0199(17) 0.0297(17) C21 0.109(3) 0.069(2) 0.097(3) 0.054(2) 0.050(2) 0.044(2) C23 0.073(2) 0.077(3) 0.088(3) 0.026(2) 0.020(2) 0.035(2) C20 0.087(2) 0.063(2) 0.074(2) 0.0416(19) 0.0398(19) 0.0345(18) C26 0.063(2) 0.060(2) 0.083(3) 0.0293(19) 0.0198(18) 0.0192(17) C22 0.098(3) 0.064(2) 0.091(3) 0.042(2) 0.038(2) 0.045(2) C25 0.069(2) 0.078(3) 0.118(4) 0.041(3) 0.029(2) 0.019(2) C24 0.066(2) 0.091(3) 0.116(4) 0.036(3) 0.029(2) 0.024(2) N6 0.0659(18) 0.0453(15) 0.077(2) 0.0302(15) 0.0264(15) 0.0205(14) N7 0.0589(16) 0.0476(15) 0.0726(19) 0.0321(14) 0.0301(14) 0.0201(13) N8 0.0629(16) 0.0464(14) 0.0777(19) 0.0301(14) 0.0322(14) 0.0204(12) C31 0.066(2) 0.0458(17) 0.065(2) 0.0249(16) 0.0234(16) 0.0164(15) C32 0.069(2) 0.0492(18) 0.074(2) 0.0272(17) 0.0218(17) 0.0180(16) C36 0.073(2) 0.0443(18) 0.108(3) 0.030(2) 0.035(2) 0.0173(17) C33 0.089(3) 0.0434(18) 0.086(3) 0.0279(19) 0.026(2) 0.0149(18) C35 0.070(2) 0.057(2) 0.132(4) 0.032(2) 0.042(2) 0.0117(18) C34 0.080(3) 0.054(2) 0.119(4) 0.036(2) 0.036(2) 0.0059(19) C30 0.0600(19) 0.0474(17) 0.059(2) 0.0258(15) 0.0226(15) 0.0196(14) O6 0.0636(14) 0.0561(13) 0.0949(18) 0.0367(13) 0.0317(12) 0.0251(11) O8 0.160(3) 0.075(2) 0.229(5) 0.089(3) 0.078(3) 0.023(2) O7 0.127(3) 0.076(2) 0.239(5) 0.083(3) 0.069(3) 0.049(2) O10 0.098(2) 0.093(3) 0.413(8) 0.108(4) 0.115(4) 0.043(2) O9 0.099(2) 0.119(3) 0.350(7) 0.106(4) 0.109(4) 0.022(2) N9 0.109(3) 0.055(2) 0.138(3) 0.050(2) 0.032(3) 0.017(2) N10 0.079(3) 0.083(3) 0.246(6) 0.065(3) 0.072(3) 0.017(2) C29 0.0659(19) 0.0504(17) 0.0542(19) 0.0269(15) 0.0347(16) 0.0264(14) C37 0.112(3) 0.093(3) 0.083(3) 0.045(2) 0.059(3) 0.033(2) C39 0.217(8) 0.171(7) 0.196(8) 0.110(6) 0.113(6) 0.021(6) C38 0.145(4) 0.134(5) 0.125(4) 0.073(4) 0.081(4) 0.022(4) C40 0.292(13) 0.324(15) 0.273(13) 0.168(12) 0.090(10) -0.077(12) C41 0.088(3) 0.096(3) 0.062(2) 0.032(2) 0.029(2) 0.014(2) C42 0.092(3) 0.138(4) 0.105(4) 0.056(3) 0.034(3) 0.028(3) C44 0.151(7) 0.362(15) 0.168(8) 0.075(9) 0.046(6) 0.073(8) C43 0.088(3) 0.220(7) 0.132(5) 0.081(5) 0.035(3) 0.044(4) C45 0.088(3) 0.079(3) 0.062(2) 0.021(2) 0.030(2) 0.026(2) C46 0.085(3) 0.089(3) 0.079(3) 0.038(2) 0.035(2) 0.028(2) C47 0.087(3) 0.087(3) 0.105(3) 0.034(3) 0.030(2) 0.023(2) C48 0.112(4) 0.100(4) 0.157(5) 0.063(4) 0.050(3) 0.019(3) C49 0.099(3) 0.081(3) 0.075(3) 0.033(2) 0.053(2) 0.030(2) C50 0.116(4) 0.161(5) 0.104(4) 0.068(4) 0.064(3) 0.075(4) C51 0.146(5) 0.163(5) 0.169(6) 0.087(5) 0.102(4) 0.083(4) C52 0.69(3) 0.53(2) 0.55(3) 0.44(2) 0.53(3) 0.52(3) C53 0.079(2) 0.083(2) 0.059(2) 0.031(2) 0.0392(19) 0.0255(19) C54 0.080(2) 0.090(3) 0.071(3) 0.029(2) 0.038(2) 0.019(2) C55 0.097(3) 0.101(3) 0.101(3) 0.039(3) 0.053(3) 0.021(3) C56 0.131(4) 0.127(4) 0.126(5) 0.047(4) 0.059(4) 0.007(4) C59 0.101(3) 0.079(2) 0.067(2) 0.032(2) 0.045(2) 0.032(2) C57 0.077(2) 0.076(2) 0.052(2) 0.0227(18) 0.0349(17) 0.0226(18) C58 0.097(3) 0.107(3) 0.069(3) 0.045(2) 0.047(2) 0.047(2) C60 0.144(4) 0.117(4) 0.104(4) 0.065(3) 0.075(3) 0.073(3) C61 0.074(2) 0.086(2) 0.048(2) 0.0191(18) 0.0259(17) 0.0246(19) C62 0.074(2) 0.090(3) 0.072(3) 0.020(2) 0.032(2) 0.019(2) C63 0.080(3) 0.110(4) 0.092(3) 0.015(3) 0.021(2) 0.017(3) C64 0.077(3) 0.121(4) 0.142(5) 0.020(4) 0.027(3) 0.007(3) C65 0.075(2) 0.078(2) 0.060(2) 0.0304(19) 0.0277(18) 0.0212(18) C66 0.078(2) 0.077(2) 0.071(2) 0.026(2) 0.0325(19) 0.0219(19) C67 0.143(4) 0.123(4) 0.112(4) 0.066(3) 0.068(3) 0.074(3) C68 0.160(5) 0.125(4) 0.162(6) 0.082(4) 0.085(4) 0.069(4) N12 0.0712(17) 0.0731(18) 0.0511(17) 0.0253(14) 0.0311(14) 0.0227(14) N11 0.086(2) 0.082(2) 0.0601(19) 0.0298(17) 0.0386(16) 0.0237(16) O11 0.115(3) 0.180(4) 0.102(3) 0.078(3) 0.065(2) 0.050(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 S2 C29 1.679(3) . ? C9 C8 1.392(7) . ? C9 C1 1.438(7) . ? C9 C10 1.450(7) . ? C1 C2 1.370(6) . ? C1 N1 1.399(5) . ? C4 C3 1.331(11) . ? C4 C10 1.384(10) . ? C2 C3 1.446(9) . ? C10 C5 1.422(10) . ? C8 C7 1.354(7) . ? C6 C5 1.357(10) . ? C6 C7 1.387(9) . ? C13 C14 1.380(5) . ? C13 C18 1.402(5) . ? C13 C12 1.495(5) . ? C12 O1 1.263(4) . ? C12 N3 1.311(4) . ? C18 C17 1.375(5) . ? C14 C15 1.370(5) . ? C17 C16 1.382(5) . ? C17 N5 1.466(5) . ? C16 C15 1.374(5) . ? C11 N2 1.339(5) . ? C11 N1 1.353(5) . ? C11 S1 1.679(4) . ? C15 N4 1.470(5) . ? N3 N2 1.397(4) . ? N5 O4 1.199(4) . ? N5 O5 1.222(4) . ? N4 O3 1.214(5) . ? N4 O2 1.215(5) . ? C19 C20 1.364(4) . ? C19 N6 1.416(4) . ? C19 C27 1.427(5) . ? C27 C26 1.395(5) . ? C27 C28 1.435(4) . ? C28 C22 1.399(5) . ? C28 C23 1.414(5) . ? C21 C22 1.350(5) . ? C21 C20 1.408(5) . ? C23 C24 1.346(6) . ? C26 C25 1.354(5) . ? C25 C24 1.407(5) . ? N6 C29 1.352(4) . ? N7 C29 1.339(4) . ? N7 N8 1.399(4) . ? N8 C30 1.312(4) . ? C31 C36 1.377(4) . ? C31 C32 1.388(4) . ? C31 C30 1.503(4) . ? C32 C33 1.390(5) . ? C36 C35 1.369(5) . ? C33 C34 1.349(5) . ? C33 N9 1.475(5) . ? C35 C34 1.377(5) . ? C35 N10 1.476(5) . ? C30 O6 1.254(3) . ? O8 N9 1.210(5) . ? O7 N9 1.213(5) . ? O10 N10 1.189(5) . ? O9 N10 1.215(5) . ? C37 N11 1.502(5) . ? C37 C38 1.499(6) . ? C39 C40 1.460(7) . ? C39 C38 1.530(7) . ? C41 C42 1.505(6) . ? C41 N11 1.514(5) . ? C42 C43 1.527(7) . ? C44 C43 1.367(9) . ? C45 C46 1.505(5) . ? C45 N11 1.527(5) . ? C46 C47 1.519(6) . ? C47 C48 1.495(6) . ? C49 N11 1.511(4) . ? C49 C50 1.515(6) . ? C50 C51 1.509(6) . ? C51 C52 1.460(7) . ? C53 C54 1.505(5) . ? C53 N12 1.510(4) . ? C54 C55 1.529(5) . ? C55 C56 1.498(7) . ? C59 C60 1.501(5) . ? C59 C58 1.500(5) . ? C57 C58 1.500(5) . ? C57 N12 1.522(4) . ? C61 C62 1.510(5) . ? C61 N12 1.516(4) . ? C62 C63 1.513(6) . ? C63 C64 1.519(7) . ? C65 C66 1.512(5) . ? C65 N12 1.517(4) . ? C66 C67 1.528(5) . ? C67 C68 1.505(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 C8 C9 C1 125.5(4) . . ? C8 C9 C10 117.1(6) . . ? C1 C9 C10 117.4(5) . . ? C2 C1 N1 122.7(5) . . ? C2 C1 C9 122.2(5) . . ? N1 C1 C9 115.1(4) . . ? C3 C4 C10 123.0(7) . . ? C1 C2 C3 117.5(6) . . ? C4 C10 C5 124.0(7) . . ? C4 C10 C9 118.5(7) . . ? C5 C10 C9 117.5(7) . . ? C4 C3 C2 121.3(7) . . ? C7 C8 C9 123.4(5) . . ? C5 C6 C7 120.0(7) . . ? C8 C7 C6 119.9(7) . . ? C6 C5 C10 122.0(7) . . ? C14 C13 C18 118.5(3) . . ? C14 C13 C12 119.6(3) . . ? C18 C13 C12 121.9(3) . . ? O1 C12 N3 127.1(3) . . ? O1 C12 C13 119.3(3) . . ? N3 C12 C13 113.6(3) . . ? C17 C18 C13 119.4(3) . . ? C15 C14 C13 120.0(3) . . ? C18 C17 C16 122.8(3) . . ? C18 C17 N5 118.7(3) . . ? C16 C17 N5 118.5(3) . . ? C15 C16 C17 116.2(3) . . ? N2 C11 N1 112.6(3) . . ? N2 C11 S1 118.7(3) . . ? N1 C11 S1 128.7(3) . . ? C14 C15 C16 123.2(4) . . ? C14 C15 N4 119.1(4) . . ? C16 C15 N4 117.7(4) . . ? C12 N3 N2 110.7(3) . . ? C11 N2 N3 121.4(3) . . ? C11 N1 C1 133.7(4) . . ? O4 N5 O5 123.6(4) . . ? O4 N5 C17 118.3(3) . . ? O5 N5 C17 118.1(4) . . ? O3 N4 O2 124.3(4) . . ? O3 N4 C15 117.7(5) . . ? O2 N4 C15 118.0(4) . . ? C20 C19 N6 122.9(3) . . ? C20 C19 C27 120.8(3) . . ? N6 C19 C27 116.3(3) . . ? C26 C27 C19 124.6(3) . . ? C26 C27 C28 117.7(3) . . ? C19 C27 C28 117.7(3) . . ? C22 C28 C23 122.3(3) . . ? C22 C28 C27 119.4(3) . . ? C23 C28 C27 118.3(3) . . ? C22 C21 C20 120.9(4) . . ? C24 C23 C28 121.7(4) . . ? C19 C20 C21 120.1(3) . . ? C25 C26 C27 122.5(3) . . ? C21 C22 C28 121.1(3) . . ? C26 C25 C24 119.8(4) . . ? C23 C24 C25 120.0(4) . . ? C29 N6 C19 131.1(3) . . ? C29 N7 N8 119.4(3) . . ? C30 N8 N7 113.2(2) . . ? C36 C31 C32 119.1(3) . . ? C36 C31 C30 122.1(3) . . ? C32 C31 C30 118.8(3) . . ? C31 C32 C33 118.4(3) . . ? C35 C36 C31 119.9(3) . . ? C34 C33 C32 123.4(3) . . ? C34 C33 N9 118.4(4) . . ? C32 C33 N9 118.2(4) . . ? C36 C35 C34 122.5(4) . . ? C36 C35 N10 117.9(3) . . ? C34 C35 N10 119.5(4) . . ? C33 C34 C35 116.7(3) . . ? O6 C30 N8 127.8(3) . . ? O6 C30 C31 118.5(3) . . ? N8 C30 C31 113.6(3) . . ? O8 N9 O7 124.4(4) . . ? O8 N9 C33 117.4(4) . . ? O7 N9 C33 118.3(4) . . ? O10 N10 O9 122.8(4) . . ? O10 N10 C35 119.4(4) . . ? O9 N10 C35 117.7(4) . . ? N7 C29 N6 112.5(3) . . ? N7 C29 S2 120.7(2) . . ? N6 C29 S2 126.8(2) . . ? N11 C37 C38 114.9(4) . . ? C40 C39 C38 109.8(7) . . ? C37 C38 C39 106.5(5) . . ? C42 C41 N11 115.7(3) . . ? C41 C42 C43 110.3(5) . . ? C44 C43 C42 116.7(6) . . ? C46 C45 N11 116.7(3) . . ? C45 C46 C47 110.6(4) . . ? C48 C47 C46 113.5(4) . . ? N11 C49 C50 116.1(3) . . ? C51 C50 C49 107.3(4) . . ? C52 C51 C50 115.9(6) . . ? C54 C53 N12 117.3(3) . . ? C53 C54 C55 109.1(3) . . ? C56 C55 C54 115.0(4) . . ? C60 C59 C58 115.1(3) . . ? C58 C57 N12 117.2(3) . . ? C57 C58 C59 110.4(3) . . ? C62 C61 N12 116.5(3) . . ? C61 C62 C63 110.7(4) . . ? C62 C63 C64 111.3(4) . . ? C66 C65 N12 117.7(3) . . ? C65 C66 C67 108.3(3) . . ? C68 C67 C66 116.0(4) . . ? C53 N12 C61 105.4(2) . . ? C53 N12 C65 111.4(3) . . ? C61 N12 C65 112.0(3) . . ? C53 N12 C57 111.7(3) . . ? C61 N12 C57 111.4(3) . . ? C65 N12 C57 105.1(2) . . ? C37 N11 C49 111.0(3) . . ? C37 N11 C41 111.0(3) . . ? C49 N11 C41 106.5(3) . . ? C37 N11 C45 106.0(3) . . ? C49 N11 C45 111.0(3) . . ? C41 N11 C45 111.5(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 24.77 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.794 _refine_diff_density_min -0.419 _refine_diff_density_rms 0.047