# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_811GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 889067' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C36 H24 N6 S4' _chemical_formula_sum 'C36 H24 N6 S4' _chemical_melting_point ? _exptl_crystal_description prism _exptl_crystal_colour colourless _diffrn_ambient_temperature 293(2) _chemical_formula_weight 668.89 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0031 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_int_tables_number 15 _symmetry_space_group_name_Hall '-C 2yc' _chemical_absolute_configuration . 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' '-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 19.3210(17) _cell_length_b 9.8395(8) _cell_length_c 17.5549(16) _cell_angle_alpha 90.00 _cell_angle_beta 107.090(2) _cell_angle_gamma 90.00 _cell_volume 3190.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5086 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 31.66 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.250 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.335 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.899 _exptl_absorpt_correction_T_max 0.924 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'kappa X8 APEX II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29991 _diffrn_reflns_av_R_equivalents 0.0284 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -29 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.21 _diffrn_reflns_theta_max 38.45 _reflns_number_total 8474 _reflns_number_gt 4597 _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, 1997)' _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^)+(0.0733P)^2^+3.2467P] 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 8474 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1178 _refine_ls_R_factor_gt 0.0592 _refine_ls_wR_factor_ref 0.1874 _refine_ls_wR_factor_gt 0.1422 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.12951(9) 0.51557(18) 0.54343(11) 0.0411(3) Uani 1 1 d . . . C2 C 0.18305(11) 0.4118(2) 0.53498(14) 0.0536(5) Uani 1 1 d . . . H2A H 0.2031 0.4387 0.4933 0.080 Uiso 1 1 calc R . . H2B H 0.1594 0.3255 0.5219 0.080 Uiso 1 1 calc R . . H2C H 0.2212 0.4043 0.5843 0.080 Uiso 1 1 calc R . . C3 C 0.11651(8) 0.64187(17) 0.51008(10) 0.0372(3) Uani 1 1 d . . . C4 C 0.03766(9) 0.65053(18) 0.57861(10) 0.0394(3) Uani 1 1 d . . . C5 C -0.01810(10) 0.7010(2) 0.61224(11) 0.0442(4) Uani 1 1 d . . . C6 C -0.04125(15) 0.8349(3) 0.60316(17) 0.0665(6) Uani 1 1 d . . . H6 H -0.0221 0.8958 0.5742 0.080 Uiso 1 1 calc R . . C7 C -0.09315(19) 0.8761(3) 0.6379(2) 0.0894(10) Uani 1 1 d . . . H7 H -0.1101 0.9651 0.6322 0.107 Uiso 1 1 calc R . . C8 C -0.11966(16) 0.7830(4) 0.68128(18) 0.0813(8) Uani 1 1 d . . . H8 H -0.1542 0.8082 0.7059 0.098 Uiso 1 1 calc R . . C9 C -0.09375(13) 0.6536(3) 0.68694(14) 0.0665(6) Uani 1 1 d . . . H9 H -0.1118 0.5914 0.7162 0.080 Uiso 1 1 calc R . . C10 C 0.15132(8) 0.69984(17) 0.45337(10) 0.0374(3) Uani 1 1 d . . . C11 C 0.22010(7) 0.74859(16) 0.46289(9) 0.0339(3) Uani 1 1 d . . . C12 C 0.17295(8) 0.79642(16) 0.33447(9) 0.0348(3) Uani 1 1 d . . . C13 C 0.16786(9) 0.85093(17) 0.25512(10) 0.0380(3) Uani 1 1 d . . . C14 C 0.22582(11) 0.9199(2) 0.24156(13) 0.0559(5) Uani 1 1 d . . . H14 H 0.2691 0.9275 0.2824 0.067 Uiso 1 1 calc R . . C15 C 0.22002(15) 0.9775(3) 0.16819(16) 0.0707(7) Uani 1 1 d . . . H15 H 0.2591 1.0237 0.1598 0.085 Uiso 1 1 calc R . . C16 C 0.15568(16) 0.9661(3) 0.10697(15) 0.0691(7) Uani 1 1 d . . . H16 H 0.1513 1.0063 0.0578 0.083 Uiso 1 1 calc R . . C17 C 0.09855(14) 0.8955(3) 0.11905(14) 0.0646(6) Uani 1 1 d . . . H17 H 0.0559 0.8858 0.0776 0.078 Uiso 1 1 calc R . . C18 C 0.10418(11) 0.8386(2) 0.19258(12) 0.0519(4) Uani 1 1 d . . . H18 H 0.0650 0.7917 0.2004 0.062 Uiso 1 1 calc R . . N1 N 0.06405(7) 0.71818(15) 0.52929(9) 0.0390(3) Uani 1 1 d . . . N2 N 0.23117(7) 0.80276(15) 0.39500(8) 0.0364(3) Uani 1 1 d . . . N3 N -0.04405(9) 0.6099(2) 0.65327(10) 0.0535(4) Uani 1 1 d . . . S1 S 0.07399(2) 0.49033(5) 0.60305(3) 0.04466(13) Uani 1 1 d . . . S2 S 0.10006(2) 0.72102(5) 0.35572(3) 0.04510(13) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0330(7) 0.0440(9) 0.0454(8) -0.0008(7) 0.0100(6) -0.0075(6) C2 0.0454(9) 0.0489(11) 0.0665(12) -0.0003(9) 0.0163(9) 0.0002(8) C3 0.0286(6) 0.0419(8) 0.0403(7) 0.0009(6) 0.0091(5) -0.0095(6) C4 0.0337(7) 0.0447(9) 0.0397(7) -0.0033(6) 0.0107(6) -0.0085(6) C5 0.0382(8) 0.0543(10) 0.0410(8) -0.0065(7) 0.0133(7) -0.0075(7) C6 0.0770(15) 0.0537(12) 0.0815(16) -0.0078(11) 0.0433(14) -0.0043(11) C7 0.104(2) 0.0693(18) 0.116(3) -0.0201(16) 0.064(2) 0.0085(16) C8 0.0744(17) 0.106(2) 0.0787(17) -0.0123(16) 0.0458(15) 0.0093(15) C9 0.0573(12) 0.0973(19) 0.0533(12) 0.0079(12) 0.0294(10) 0.0001(12) C10 0.0273(6) 0.0436(8) 0.0402(7) 0.0013(6) 0.0083(5) -0.0078(6) C11 0.0265(6) 0.0379(7) 0.0384(7) -0.0033(6) 0.0110(5) -0.0066(5) C12 0.0299(6) 0.0359(7) 0.0389(7) -0.0021(6) 0.0105(5) -0.0027(5) C13 0.0366(7) 0.0357(8) 0.0415(8) -0.0005(6) 0.0111(6) -0.0012(6) C14 0.0476(10) 0.0667(13) 0.0521(10) 0.0082(9) 0.0128(8) -0.0155(9) C15 0.0734(15) 0.0753(16) 0.0677(14) 0.0211(12) 0.0276(12) -0.0156(12) C16 0.0863(18) 0.0666(15) 0.0540(12) 0.0215(11) 0.0200(12) 0.0118(13) C17 0.0579(12) 0.0785(16) 0.0508(11) 0.0092(11) 0.0055(9) 0.0077(11) C18 0.0411(9) 0.0647(12) 0.0458(9) 0.0023(8) 0.0066(7) -0.0019(8) N1 0.0307(6) 0.0436(7) 0.0429(7) -0.0004(6) 0.0112(5) -0.0067(5) N2 0.0287(5) 0.0424(7) 0.0391(6) -0.0044(5) 0.0114(5) -0.0066(5) N3 0.0458(8) 0.0703(11) 0.0484(8) 0.0087(8) 0.0198(7) -0.0005(8) S1 0.0418(2) 0.0455(2) 0.0475(2) 0.00477(17) 0.01435(18) -0.00859(17) S2 0.02769(18) 0.0569(3) 0.0471(2) 0.00769(19) 0.00542(15) -0.01061(16) _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 C3 1.365(2) . ? C1 C2 1.492(3) . ? C1 S1 1.7227(18) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 N1 1.380(2) . ? C3 C10 1.471(2) . ? C4 N1 1.309(2) . ? C4 C5 1.459(2) . ? C4 S1 1.7275(19) . ? C5 N3 1.337(2) . ? C5 C6 1.385(3) . ? C6 C7 1.379(3) . ? C6 H6 0.9300 . ? C7 C8 1.382(4) . ? C7 H7 0.9300 . ? C8 C9 1.361(4) . ? C8 H8 0.9300 . ? C9 N3 1.338(3) . ? C9 H9 0.9300 . ? C10 C11 1.3759(19) . ? C10 S2 1.7219(17) . ? C11 N2 1.379(2) . ? C11 C11 1.466(3) 7_566 ? C12 N2 1.302(2) . ? C12 C13 1.469(2) . ? C12 S2 1.7267(15) . ? C13 C14 1.389(2) . ? C13 C18 1.393(2) . ? C14 C15 1.381(3) . ? C14 H14 0.9300 . ? C15 C16 1.388(4) . ? C15 H15 0.9300 . ? C16 C17 1.373(4) . ? C16 H16 0.9300 . ? C17 C18 1.381(3) . ? C17 H17 0.9300 . ? C18 H18 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 C3 C1 C2 128.77(17) . . ? C3 C1 S1 108.83(13) . . ? C2 C1 S1 122.38(14) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 N1 116.50(14) . . ? C1 C3 C10 125.47(16) . . ? N1 C3 C10 117.97(15) . . ? N1 C4 C5 124.89(17) . . ? N1 C4 S1 114.81(13) . . ? C5 C4 S1 120.30(13) . . ? N3 C5 C6 122.72(19) . . ? N3 C5 C4 115.34(18) . . ? C6 C5 C4 121.94(18) . . ? C7 C6 C5 118.7(2) . . ? C7 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C7 C8 119.0(3) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C9 C8 C7 118.2(2) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? N3 C9 C8 124.4(2) . . ? N3 C9 H9 117.8 . . ? C8 C9 H9 117.8 . . ? C11 C10 C3 132.11(15) . . ? C11 C10 S2 109.34(12) . . ? C3 C10 S2 118.50(11) . . ? C10 C11 N2 114.81(13) . . ? C10 C11 C11 126.54(18) . 7_566 ? N2 C11 C11 118.62(15) . 7_566 ? N2 C12 C13 123.88(14) . . ? N2 C12 S2 114.09(12) . . ? C13 C12 S2 122.02(12) . . ? C14 C13 C18 118.52(17) . . ? C14 C13 C12 120.56(15) . . ? C18 C13 C12 120.89(16) . . ? C15 C14 C13 120.8(2) . . ? C15 C14 H14 119.6 . . ? C13 C14 H14 119.6 . . ? C14 C15 C16 119.8(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C17 C16 C15 119.9(2) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.2(2) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C17 C18 C13 120.7(2) . . ? C17 C18 H18 119.7 . . ? C13 C18 H18 119.7 . . ? C4 N1 C3 109.98(15) . . ? C12 N2 C11 111.75(12) . . ? C5 N3 C9 117.0(2) . . ? C1 S1 C4 89.87(8) . . ? C10 S2 C12 90.00(7) . . ? 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 C2 C1 C3 N1 -178.97(17) . . . . ? S1 C1 C3 N1 -0.63(18) . . . . ? C2 C1 C3 C10 3.8(3) . . . . ? S1 C1 C3 C10 -177.86(13) . . . . ? N1 C4 C5 N3 171.86(16) . . . . ? S1 C4 C5 N3 -8.1(2) . . . . ? N1 C4 C5 C6 -9.2(3) . . . . ? S1 C4 C5 C6 170.80(18) . . . . ? N3 C5 C6 C7 0.0(4) . . . . ? C4 C5 C6 C7 -178.8(2) . . . . ? C5 C6 C7 C8 0.8(5) . . . . ? C6 C7 C8 C9 -0.8(5) . . . . ? C7 C8 C9 N3 0.1(5) . . . . ? C1 C3 C10 C11 -73.3(3) . . . . ? N1 C3 C10 C11 109.5(2) . . . . ? C1 C3 C10 S2 109.56(17) . . . . ? N1 C3 C10 S2 -67.64(19) . . . . ? C3 C10 C11 N2 -176.39(18) . . . . ? S2 C10 C11 N2 0.91(19) . . . . ? C3 C10 C11 C11 1.7(4) . . . 7_566 ? S2 C10 C11 C11 179.00(19) . . . 7_566 ? N2 C12 C13 C14 -3.2(3) . . . . ? S2 C12 C13 C14 175.18(16) . . . . ? N2 C12 C13 C18 178.91(18) . . . . ? S2 C12 C13 C18 -2.7(2) . . . . ? C18 C13 C14 C15 1.3(3) . . . . ? C12 C13 C14 C15 -176.6(2) . . . . ? C13 C14 C15 C16 -0.2(4) . . . . ? C14 C15 C16 C17 -1.3(4) . . . . ? C15 C16 C17 C18 1.7(4) . . . . ? C16 C17 C18 C13 -0.6(4) . . . . ? C14 C13 C18 C17 -0.9(3) . . . . ? C12 C13 C18 C17 177.0(2) . . . . ? C5 C4 N1 C3 179.12(15) . . . . ? S1 C4 N1 C3 -0.92(18) . . . . ? C1 C3 N1 C4 1.0(2) . . . . ? C10 C3 N1 C4 178.46(14) . . . . ? C13 C12 N2 C11 177.65(15) . . . . ? S2 C12 N2 C11 -0.88(18) . . . . ? C10 C11 N2 C12 0.0(2) . . . . ? C11 C11 N2 C12 -178.28(18) 7_566 . . . ? C6 C5 N3 C9 -0.8(3) . . . . ? C4 C5 N3 C9 178.10(18) . . . . ? C8 C9 N3 C5 0.7(4) . . . . ? C3 C1 S1 C4 0.08(13) . . . . ? C2 C1 S1 C4 178.55(16) . . . . ? N1 C4 S1 C1 0.50(14) . . . . ? C5 C4 S1 C1 -179.53(14) . . . . ? C11 C10 S2 C12 -1.13(13) . . . . ? C3 C10 S2 C12 176.59(15) . . . . ? N2 C12 S2 C10 1.20(13) . . . . ? C13 C12 S2 C10 -177.37(14) . . . . ? _diffrn_measured_fraction_theta_max 0.948 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.493 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.085 data_902GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 889068' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C37 H25 N5 O S3' _chemical_formula_sum 'C37 H25 N5 O S3' _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour colourless _diffrn_ambient_temperature 100(1) _chemical_formula_weight 651.83 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0031 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0109 0.0061 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1239 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _chemical_absolute_configuration . loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.7383(15) _cell_length_b 11.8198(17) _cell_length_c 15.4915(19) _cell_angle_alpha 93.571(3) _cell_angle_beta 106.219(3) _cell_angle_gamma 112.544(3) _cell_volume 1552.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 4295 _cell_measurement_theta_min 1.90 _cell_measurement_theta_max 23.12 _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.040 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.395 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 0.279 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.912 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'kappa X8 APEX II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25096 _diffrn_reflns_av_R_equivalents 0.0690 _diffrn_reflns_av_sigmaI/netI 0.1169 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 32.95 _reflns_number_total 10546 _reflns_number_gt 5644 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1125P)^2^+1.2929P] 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 10546 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1596 _refine_ls_R_factor_gt 0.0783 _refine_ls_wR_factor_ref 0.2448 _refine_ls_wR_factor_gt 0.2025 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 -0.1690(5) 0.2500(4) -0.1379(3) 0.0439(10) Uani 1 1 d . . . H1 H -0.1124 0.3031 -0.1697 0.053 Uiso 1 1 calc R . . C2 C -0.3311(5) 0.2117(4) -0.1654(3) 0.0418(9) Uani 1 1 d . . . H2 H -0.3814 0.2392 -0.2144 0.050 Uiso 1 1 calc R . . C3 C -0.4161(5) 0.1326(4) -0.1192(3) 0.0400(9) Uani 1 1 d . . . H3 H -0.5247 0.1058 -0.1363 0.048 Uiso 1 1 calc R . . C4 C -0.3377(5) 0.0938(3) -0.0472(3) 0.0350(8) Uani 1 1 d . . . H4 H -0.3929 0.0398 -0.0153 0.042 Uiso 1 1 calc R . . C5 C -0.1759(4) 0.1358(3) -0.0225(2) 0.0277(7) Uani 1 1 d . . . C6 C -0.0876(5) 0.0978(3) 0.0532(2) 0.0301(7) Uani 1 1 d . . . C7 C 0.1185(5) 0.0739(3) 0.1676(3) 0.0339(8) Uani 1 1 d . . . C8 C 0.2702(4) 0.0789(4) 0.2273(3) 0.0443(10) Uani 1 1 d . . . H8A H 0.3165 0.1479 0.2777 0.066 Uiso 1 1 calc R . . H8B H 0.3404 0.0892 0.1925 0.066 Uiso 1 1 calc R . . H8C H 0.2518 0.0026 0.2502 0.066 Uiso 1 1 calc R . . C9 C -0.0326(4) 0.0050(3) 0.1670(2) 0.0267(7) Uani 1 1 d . . . C10 C -0.0702(4) -0.0801(3) 0.2303(2) 0.0229(6) Uani 1 1 d . . . C11 C -0.1606(4) -0.2581(3) 0.3029(2) 0.0248(6) Uani 1 1 d . . . C12 C -0.2353(4) -0.3834(3) 0.3220(2) 0.0296(7) Uani 1 1 d . . . C13 C -0.3828(5) -0.4689(3) 0.2638(3) 0.0356(8) Uani 1 1 d . . . H13 H -0.4353 -0.4469 0.2123 0.043 Uiso 1 1 calc R . . C14 C -0.4508(5) -0.5868(3) 0.2830(3) 0.0441(10) Uani 1 1 d . . . H14 H -0.5498 -0.6433 0.2447 0.053 Uiso 1 1 calc R . . C15 C -0.3733(6) -0.6207(3) 0.3580(3) 0.0471(11) Uani 1 1 d . . . H15 H -0.4193 -0.7005 0.3697 0.057 Uiso 1 1 calc R . . C16 C -0.2269(5) -0.5371(3) 0.4163(3) 0.0421(10) Uani 1 1 d . . . H16 H -0.1747 -0.5605 0.4670 0.051 Uiso 1 1 calc R . . C17 C -0.1579(5) -0.4172(3) 0.3987(3) 0.0324(8) Uani 1 1 d . . . H17 H -0.0603 -0.3602 0.4383 0.039 Uiso 1 1 calc R . . C18 C -0.0079(3) -0.0577(3) 0.3237(2) 0.0220(6) Uani 1 1 d . . . C19 C 0.1040(4) 0.0667(3) 0.3793(2) 0.0224(6) Uani 1 1 d . . . C20 C 0.3333(4) 0.2003(3) 0.4754(2) 0.0228(6) Uani 1 1 d . . . C21 C 0.4953(4) 0.2512(3) 0.5396(2) 0.0238(6) Uani 1 1 d . . . C22 C 0.5836(4) 0.1822(3) 0.5428(2) 0.0295(7) Uani 1 1 d . . . H22 H 0.5377 0.1027 0.5070 0.035 Uiso 1 1 calc R . . C23 C 0.7396(4) 0.2308(3) 0.5988(3) 0.0319(7) Uani 1 1 d . . . H23 H 0.7979 0.1838 0.6007 0.038 Uiso 1 1 calc R . . C24 C 0.8081(4) 0.3490(3) 0.6515(2) 0.0313(8) Uani 1 1 d . . . H24 H 0.9134 0.3823 0.6881 0.038 Uiso 1 1 calc R . . C25 C 0.7211(4) 0.4182(3) 0.6503(2) 0.0288(7) Uani 1 1 d . . . H25 H 0.7669 0.4971 0.6870 0.035 Uiso 1 1 calc R . . C26 C 0.5649(4) 0.3694(3) 0.5940(2) 0.0270(7) Uani 1 1 d . . . H26 H 0.5066 0.4162 0.5926 0.032 Uiso 1 1 calc R . . C27 C 0.0820(4) 0.1734(3) 0.3689(2) 0.0226(6) Uani 1 1 d . . . C28 C -0.0558(4) 0.1877(3) 0.3130(2) 0.0235(6) Uani 1 1 d . . . C29 C -0.2085(4) 0.1210(3) 0.3069(2) 0.0284(7) Uani 1 1 d . . . C30 C -0.2866(5) 0.0234(4) 0.3533(3) 0.0467(10) Uani 1 1 d . . . H30A H -0.3246 -0.0570 0.3157 0.070 Uiso 1 1 calc R . . H30B H -0.3734 0.0353 0.3635 0.070 Uiso 1 1 calc R . . H30C H -0.2128 0.0284 0.4110 0.070 Uiso 1 1 calc R . . C31 C -0.1903(4) 0.2554(3) 0.2137(2) 0.0233(6) Uani 1 1 d . . . C32 C -0.2472(4) 0.3175(3) 0.1433(2) 0.0258(6) Uani 1 1 d . . . C33 C -0.1414(4) 0.4130(3) 0.1152(3) 0.0321(8) Uani 1 1 d . . . H33 H -0.0336 0.4377 0.1416 0.039 Uiso 1 1 calc R . . C34 C -0.1977(5) 0.4703(4) 0.0482(3) 0.0404(9) Uani 1 1 d . . . H34 H -0.1277 0.5346 0.0296 0.048 Uiso 1 1 calc R . . C35 C -0.3585(5) 0.4326(4) 0.0083(3) 0.0412(9) Uani 1 1 d . . . H35 H -0.3963 0.4715 -0.0369 0.049 Uiso 1 1 calc R . . C36 C -0.4616(5) 0.3379(4) 0.0357(3) 0.0401(9) Uani 1 1 d . . . H36 H -0.5694 0.3121 0.0082 0.048 Uiso 1 1 calc R . . C37 C -0.4078(4) 0.2809(3) 0.1027(2) 0.0305(7) Uani 1 1 d . . . H37 H -0.4789 0.2174 0.1212 0.037 Uiso 1 1 calc R . . N1 N -0.0902(4) 0.2138(3) -0.0672(2) 0.0372(7) Uani 1 1 d . . . N2 N -0.1501(4) 0.0180(3) 0.10090(19) 0.0290(6) Uani 1 1 d . . . N3 N -0.0582(3) -0.1593(2) 0.36442(19) 0.0257(6) Uani 1 1 d . . . N4 N 0.2455(3) 0.0821(2) 0.44013(18) 0.0236(5) Uani 1 1 d . . . N5 N -0.0453(3) 0.2729(2) 0.25503(18) 0.0233(5) Uani 1 1 d . . . O1 O -0.3116(3) 0.1592(2) 0.24087(15) 0.0290(6) Uani 1 1 d . . . S1 S 0.24835(9) 0.29945(7) 0.43565(6) 0.02379(18) Uani 1 1 d . . . S2 S -0.20019(10) -0.23412(7) 0.19116(6) 0.0276(2) Uani 1 1 d . . . S3 S 0.11930(13) 0.16213(9) 0.08533(7) 0.0425(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 C1 0.044(2) 0.0382(19) 0.035(2) 0.0179(16) 0.0102(18) 0.0017(18) C2 0.049(3) 0.0391(19) 0.033(2) 0.0164(16) 0.0097(18) 0.0159(18) C3 0.037(2) 0.050(2) 0.035(2) 0.0102(16) 0.0122(17) 0.0190(18) C4 0.036(2) 0.0413(19) 0.0323(19) 0.0159(15) 0.0180(16) 0.0143(16) C5 0.0316(18) 0.0230(14) 0.0249(16) 0.0072(12) 0.0126(14) 0.0049(13) C6 0.041(2) 0.0279(15) 0.0212(16) 0.0069(12) 0.0144(14) 0.0107(15) C7 0.044(2) 0.0231(15) 0.0359(19) 0.0091(13) 0.0278(17) 0.0042(15) C8 0.0263(19) 0.039(2) 0.055(3) -0.0024(17) 0.0253(18) -0.0058(16) C9 0.0298(18) 0.0258(14) 0.0263(16) 0.0079(12) 0.0145(14) 0.0094(13) C10 0.0177(14) 0.0250(14) 0.0253(15) 0.0073(11) 0.0112(12) 0.0050(12) C11 0.0197(15) 0.0253(14) 0.0301(16) 0.0095(12) 0.0149(13) 0.0049(12) C12 0.0307(18) 0.0235(14) 0.0374(19) 0.0083(13) 0.0229(15) 0.0054(13) C13 0.032(2) 0.0276(16) 0.038(2) 0.0046(14) 0.0184(16) -0.0010(15) C14 0.040(2) 0.0272(17) 0.051(2) 0.0015(16) 0.027(2) -0.0078(16) C15 0.062(3) 0.0261(17) 0.049(2) 0.0098(16) 0.038(2) 0.0007(18) C16 0.056(3) 0.0359(19) 0.042(2) 0.0181(16) 0.031(2) 0.0143(18) C17 0.035(2) 0.0294(16) 0.0355(19) 0.0128(14) 0.0206(16) 0.0089(15) C18 0.0133(14) 0.0252(14) 0.0271(16) 0.0090(11) 0.0082(12) 0.0057(11) C19 0.0183(14) 0.0245(14) 0.0236(15) 0.0108(11) 0.0082(12) 0.0064(12) C20 0.0207(15) 0.0202(13) 0.0271(16) 0.0092(11) 0.0092(12) 0.0065(12) C21 0.0184(15) 0.0215(13) 0.0255(15) 0.0108(11) 0.0066(12) 0.0018(12) C22 0.0261(17) 0.0233(14) 0.0340(18) 0.0081(13) 0.0064(14) 0.0071(13) C23 0.0244(17) 0.0337(17) 0.0376(19) 0.0119(14) 0.0080(15) 0.0128(14) C24 0.0203(16) 0.0362(17) 0.0257(17) 0.0115(13) 0.0031(13) 0.0022(14) C25 0.0256(17) 0.0261(15) 0.0257(16) 0.0078(12) 0.0074(13) 0.0019(13) C26 0.0263(17) 0.0271(15) 0.0240(16) 0.0085(12) 0.0056(13) 0.0088(13) C27 0.0170(14) 0.0268(14) 0.0228(15) 0.0098(11) 0.0081(12) 0.0061(12) C28 0.0208(15) 0.0262(14) 0.0252(15) 0.0095(12) 0.0102(12) 0.0091(12) C29 0.0186(15) 0.0339(16) 0.0345(18) 0.0105(14) 0.0121(13) 0.0100(13) C30 0.037(2) 0.050(2) 0.061(3) 0.022(2) 0.035(2) 0.0126(19) C31 0.0190(15) 0.0228(13) 0.0272(16) 0.0082(11) 0.0096(12) 0.0061(12) C32 0.0242(16) 0.0278(15) 0.0265(16) 0.0092(12) 0.0078(13) 0.0118(13) C33 0.0258(17) 0.0319(16) 0.0344(19) 0.0149(14) 0.0072(14) 0.0083(14) C34 0.037(2) 0.0363(19) 0.043(2) 0.0216(16) 0.0101(17) 0.0102(16) C35 0.047(2) 0.051(2) 0.034(2) 0.0205(17) 0.0111(18) 0.030(2) C36 0.034(2) 0.057(2) 0.035(2) 0.0109(17) 0.0074(16) 0.0277(19) C37 0.0233(17) 0.0392(18) 0.0320(18) 0.0121(14) 0.0102(14) 0.0144(15) N1 0.0358(18) 0.0343(15) 0.0305(16) 0.0144(12) 0.0123(13) 0.0012(13) N2 0.0347(16) 0.0293(13) 0.0248(14) 0.0095(11) 0.0138(12) 0.0118(12) N3 0.0202(13) 0.0233(12) 0.0307(15) 0.0097(10) 0.0104(11) 0.0039(11) N4 0.0182(13) 0.0213(12) 0.0265(14) 0.0084(10) 0.0047(10) 0.0046(10) N5 0.0186(13) 0.0260(12) 0.0250(13) 0.0096(10) 0.0074(10) 0.0081(11) O1 0.0347(16) 0.0293(13) 0.0248(14) 0.0095(11) 0.0138(12) 0.0118(12) S1 0.0203(4) 0.0207(3) 0.0281(4) 0.0090(3) 0.0072(3) 0.0061(3) S2 0.0213(4) 0.0252(4) 0.0281(4) 0.0054(3) 0.0089(3) 0.0008(3) S3 0.0432(6) 0.0369(5) 0.0413(6) 0.0119(4) 0.0211(5) 0.0049(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.345(5) . ? C1 C2 1.390(6) . ? C1 H1 0.9300 . ? C2 C3 1.377(6) . ? C2 H2 0.9300 . ? C3 C4 1.376(5) . ? C3 H3 0.9300 . ? C4 C5 1.384(5) . ? C4 H4 0.9300 . ? C5 N1 1.356(4) . ? C5 C6 1.454(5) . ? C6 N2 1.306(4) . ? C6 S3 1.762(4) . ? C7 C9 1.379(5) . ? C7 C8 1.484(6) . ? C7 S3 1.697(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N2 1.372(5) . ? C9 C10 1.466(4) . ? C10 C18 1.367(4) . ? C10 S2 1.718(3) . ? C11 N3 1.306(4) . ? C11 C12 1.469(4) . ? C11 S2 1.731(3) . ? C12 C17 1.389(5) . ? C12 C13 1.396(5) . ? C13 C14 1.387(5) . ? C13 H13 0.9300 . ? C14 C15 1.372(6) . ? C14 H14 0.9300 . ? C15 C16 1.383(6) . ? C15 H15 0.9300 . ? C16 C17 1.397(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N3 1.378(4) . ? C18 C19 1.476(4) . ? C19 C27 1.369(4) . ? C19 N4 1.372(4) . ? C20 N4 1.307(4) . ? C20 C21 1.470(4) . ? C20 S1 1.728(3) . ? C21 C22 1.387(5) . ? C21 C26 1.388(4) . ? C22 C23 1.387(5) . ? C22 H22 0.9300 . ? C23 C24 1.380(5) . ? C23 H23 0.9300 . ? C24 C25 1.383(5) . ? C24 H24 0.9300 . ? C25 C26 1.390(5) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.457(4) . ? C27 S1 1.713(3) . ? C28 C29 1.362(4) . ? C28 N5 1.384(4) . ? C29 O1 1.446(4) . ? C29 C30 1.470(5) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 0.9600 . ? C31 N5 1.304(4) . ? C31 C32 1.452(4) . ? C31 O1 1.475(4) . ? C32 C37 1.388(5) . ? C32 C33 1.395(5) . ? C33 C34 1.376(5) . ? C33 H33 0.9300 . ? C34 C35 1.386(6) . ? C34 H34 0.9300 . ? C35 C36 1.370(6) . ? C35 H35 0.9300 . ? C36 C37 1.364(5) . ? C36 H36 0.9300 . ? C37 H37 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 N1 C1 C2 123.0(4) . . ? N1 C1 H1 118.5 . . ? C2 C1 H1 118.5 . . ? C3 C2 C1 119.0(4) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C4 C3 C2 118.9(4) . . ? C4 C3 H3 120.6 . . ? C2 C3 H3 120.6 . . ? C3 C4 C5 119.5(3) . . ? C3 C4 H4 120.2 . . ? C5 C4 H4 120.2 . . ? N1 C5 C4 122.4(3) . . ? N1 C5 C6 116.0(3) . . ? C4 C5 C6 121.6(3) . . ? N2 C6 C5 124.9(3) . . ? N2 C6 S3 115.9(3) . . ? C5 C6 S3 119.2(2) . . ? C9 C7 C8 129.7(3) . . ? C9 C7 S3 111.2(3) . . ? C8 C7 S3 119.2(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N2 C9 C7 115.8(3) . . ? N2 C9 C10 120.6(3) . . ? C7 C9 C10 123.6(3) . . ? C18 C10 C9 128.8(3) . . ? C18 C10 S2 109.6(2) . . ? C9 C10 S2 121.5(2) . . ? N3 C11 C12 125.1(3) . . ? N3 C11 S2 114.7(2) . . ? C12 C11 S2 120.1(3) . . ? C17 C12 C13 119.7(3) . . ? C17 C12 C11 119.6(3) . . ? C13 C12 C11 120.7(3) . . ? C14 C13 C12 119.7(4) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 120.6(4) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C14 C15 C16 120.4(3) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C15 C16 C17 119.8(4) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C12 C17 C16 119.8(4) . . ? C12 C17 H17 120.1 . . ? C16 C17 H17 120.1 . . ? C10 C18 N3 115.6(3) . . ? C10 C18 C19 123.4(3) . . ? N3 C18 C19 121.0(3) . . ? C27 C19 N4 116.0(3) . . ? C27 C19 C18 123.8(3) . . ? N4 C19 C18 120.0(3) . . ? N4 C20 C21 125.1(3) . . ? N4 C20 S1 114.6(2) . . ? C21 C20 S1 120.2(2) . . ? C22 C21 C26 119.1(3) . . ? C22 C21 C20 119.2(3) . . ? C26 C21 C20 121.6(3) . . ? C23 C22 C21 120.6(3) . . ? C23 C22 H22 119.7 . . ? C21 C22 H22 119.7 . . ? C24 C23 C22 119.8(3) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 120.3(3) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C24 C25 C26 119.7(3) . . ? C24 C25 H25 120.2 . . ? C26 C25 H25 120.2 . . ? C21 C26 C25 120.5(3) . . ? C21 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C19 C27 C28 129.2(3) . . ? C19 C27 S1 109.3(2) . . ? C28 C27 S1 121.6(2) . . ? C29 C28 N5 110.6(3) . . ? C29 C28 C27 127.2(3) . . ? N5 C28 C27 122.1(3) . . ? C28 C29 O1 110.5(3) . . ? C28 C29 C30 134.0(3) . . ? O1 C29 C30 115.5(3) . . ? C29 C30 H30A 109.5 . . ? C29 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? C29 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? N5 C31 C32 128.1(3) . . ? N5 C31 O1 115.9(3) . . ? C32 C31 O1 116.0(3) . . ? C37 C32 C33 119.6(3) . . ? C37 C32 C31 120.0(3) . . ? C33 C32 C31 120.4(3) . . ? C34 C33 C32 119.5(3) . . ? C34 C33 H33 120.3 . . ? C32 C33 H33 120.3 . . ? C33 C34 C35 120.2(4) . . ? C33 C34 H34 119.9 . . ? C35 C34 H34 119.9 . . ? C36 C35 C34 119.9(4) . . ? C36 C35 H35 120.1 . . ? C34 C35 H35 120.1 . . ? C37 C36 C35 120.7(4) . . ? C37 C36 H36 119.6 . . ? C35 C36 H36 119.6 . . ? C36 C37 C32 120.1(3) . . ? C36 C37 H37 119.9 . . ? C32 C37 H37 119.9 . . ? C1 N1 C5 117.2(3) . . ? C6 N2 C9 109.2(3) . . ? C11 N3 C18 110.6(3) . . ? C20 N4 C19 110.4(3) . . ? C31 N5 C28 105.1(3) . . ? C29 O1 C31 98.0(2) . . ? C27 S1 C20 89.73(15) . . ? C10 S2 C11 89.49(15) . . ? C7 S3 C6 87.89(18) . . ? 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 N1 C1 C2 C3 -0.4(7) . . . . ? C1 C2 C3 C4 -0.1(6) . . . . ? C2 C3 C4 C5 0.5(6) . . . . ? C3 C4 C5 N1 -0.5(6) . . . . ? C3 C4 C5 C6 179.8(3) . . . . ? N1 C5 C6 N2 -176.0(3) . . . . ? C4 C5 C6 N2 3.8(5) . . . . ? N1 C5 C6 S3 4.0(4) . . . . ? C4 C5 C6 S3 -176.2(3) . . . . ? C8 C7 C9 N2 -178.0(3) . . . . ? S3 C7 C9 N2 1.5(4) . . . . ? C8 C7 C9 C10 0.4(6) . . . . ? S3 C7 C9 C10 179.9(3) . . . . ? N2 C9 C10 C18 -130.5(4) . . . . ? C7 C9 C10 C18 51.1(5) . . . . ? N2 C9 C10 S2 53.6(4) . . . . ? C7 C9 C10 S2 -124.8(3) . . . . ? N3 C11 C12 C17 -26.5(5) . . . . ? S2 C11 C12 C17 150.7(3) . . . . ? N3 C11 C12 C13 153.7(4) . . . . ? S2 C11 C12 C13 -29.1(5) . . . . ? C17 C12 C13 C14 -0.1(6) . . . . ? C11 C12 C13 C14 179.8(3) . . . . ? C12 C13 C14 C15 -1.0(6) . . . . ? C13 C14 C15 C16 0.9(6) . . . . ? C14 C15 C16 C17 0.1(6) . . . . ? C13 C12 C17 C16 1.1(5) . . . . ? C11 C12 C17 C16 -178.8(3) . . . . ? C15 C16 C17 C12 -1.1(6) . . . . ? C9 C10 C18 N3 -175.1(3) . . . . ? S2 C10 C18 N3 1.1(4) . . . . ? C9 C10 C18 C19 6.0(5) . . . . ? S2 C10 C18 C19 -177.8(2) . . . . ? C10 C18 C19 C27 47.9(5) . . . . ? N3 C18 C19 C27 -130.9(3) . . . . ? C10 C18 C19 N4 -126.2(3) . . . . ? N3 C18 C19 N4 54.9(4) . . . . ? N4 C20 C21 C22 22.1(5) . . . . ? S1 C20 C21 C22 -154.2(3) . . . . ? N4 C20 C21 C26 -161.2(3) . . . . ? S1 C20 C21 C26 22.4(4) . . . . ? C26 C21 C22 C23 -0.5(5) . . . . ? C20 C21 C22 C23 176.2(3) . . . . ? C21 C22 C23 C24 -0.3(5) . . . . ? C22 C23 C24 C25 1.4(5) . . . . ? C23 C24 C25 C26 -1.5(5) . . . . ? C22 C21 C26 C25 0.4(5) . . . . ? C20 C21 C26 C25 -176.3(3) . . . . ? C24 C25 C26 C21 0.6(5) . . . . ? N4 C19 C27 C28 -177.3(3) . . . . ? C18 C19 C27 C28 8.3(5) . . . . ? N4 C19 C27 S1 1.9(4) . . . . ? C18 C19 C27 S1 -172.5(2) . . . . ? C19 C27 C28 C29 46.6(5) . . . . ? S1 C27 C28 C29 -132.6(3) . . . . ? C19 C27 C28 N5 -131.2(4) . . . . ? S1 C27 C28 N5 49.6(4) . . . . ? N5 C28 C29 O1 0.7(4) . . . . ? C27 C28 C29 O1 -177.3(3) . . . . ? N5 C28 C29 C30 -177.9(4) . . . . ? C27 C28 C29 C30 4.1(7) . . . . ? N5 C31 C32 C37 175.9(3) . . . . ? O1 C31 C32 C37 -3.1(5) . . . . ? N5 C31 C32 C33 -3.4(5) . . . . ? O1 C31 C32 C33 177.7(3) . . . . ? C37 C32 C33 C34 0.6(6) . . . . ? C31 C32 C33 C34 179.8(3) . . . . ? C32 C33 C34 C35 -0.6(6) . . . . ? C33 C34 C35 C36 0.0(7) . . . . ? C34 C35 C36 C37 0.8(6) . . . . ? C35 C36 C37 C32 -0.8(6) . . . . ? C33 C32 C37 C36 0.2(5) . . . . ? C31 C32 C37 C36 -179.1(3) . . . . ? C2 C1 N1 C5 0.5(6) . . . . ? C4 C5 N1 C1 0.0(5) . . . . ? C6 C5 N1 C1 179.7(3) . . . . ? C5 C6 N2 C9 -179.6(3) . . . . ? S3 C6 N2 C9 0.4(4) . . . . ? C7 C9 N2 C6 -1.2(4) . . . . ? C10 C9 N2 C6 -179.7(3) . . . . ? C12 C11 N3 C18 178.3(3) . . . . ? S2 C11 N3 C18 0.9(4) . . . . ? C10 C18 N3 C11 -1.3(4) . . . . ? C19 C18 N3 C11 177.6(3) . . . . ? C21 C20 N4 C19 -176.9(3) . . . . ? S1 C20 N4 C19 -0.4(4) . . . . ? C27 C19 N4 C20 -1.0(4) . . . . ? C18 C19 N4 C20 173.6(3) . . . . ? C32 C31 N5 C28 -177.8(3) . . . . ? O1 C31 N5 C28 1.1(4) . . . . ? C29 C28 N5 C31 -1.1(4) . . . . ? C27 C28 N5 C31 177.0(3) . . . . ? C28 C29 O1 C31 0.0(3) . . . . ? C30 C29 O1 C31 178.9(3) . . . . ? N5 C31 O1 C29 -0.7(3) . . . . ? C32 C31 O1 C29 178.4(3) . . . . ? C19 C27 S1 C20 -1.7(3) . . . . ? C28 C27 S1 C20 177.6(3) . . . . ? N4 C20 S1 C27 1.2(3) . . . . ? C21 C20 S1 C27 177.9(3) . . . . ? C18 C10 S2 C11 -0.5(3) . . . . ? C9 C10 S2 C11 176.1(3) . . . . ? N3 C11 S2 C10 -0.3(3) . . . . ? C12 C11 S2 C10 -177.8(3) . . . . ? C9 C7 S3 C6 -1.0(3) . . . . ? C8 C7 S3 C6 178.6(3) . . . . ? N2 C6 S3 C7 0.4(3) . . . . ? C5 C6 S3 C7 -179.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.886 _refine_diff_density_min -0.700 _refine_diff_density_rms 0.101 data_886GuillotICMMO _database_code_depnum_ccdc_archive 'CCDC 889294' _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_formula_moiety 'C38 H26 N4 S4' _chemical_formula_sum 'C38 H26 N4 S4' _chemical_properties_physical photo-sensitive _chemical_melting_point ? _exptl_crystal_description ? _exptl_crystal_colour ? _diffrn_ambient_temperature 100(1) _chemical_formula_weight 666.91 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0031 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1250 0.1239 '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/n' _symmetry_int_tables_number 14 _chemical_absolute_configuration . 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 11.9309(6) _cell_length_b 13.5973(7) _cell_length_c 19.9102(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.9330(10) _cell_angle_gamma 90.00 _cell_volume 3212.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(1) _cell_measurement_reflns_used 7291 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 36.72 _exptl_crystal_size_max 0.310 _exptl_crystal_size_mid 0.270 _exptl_crystal_size_min 0.210 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1384 _exptl_absorpt_coefficient_mu 0.331 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.911 _exptl_absorpt_correction_T_max 0.942 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'kappa X8 APEX II Bruker ICMMO' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 57823 _diffrn_reflns_av_R_equivalents 0.0319 _diffrn_reflns_av_sigmaI/netI 0.0373 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.91 _diffrn_reflns_theta_max 36.72 _reflns_number_total 15517 _reflns_number_gt 11572 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0547P)^2^+1.0416P] 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 15517 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1113 _refine_ls_wR_factor_gt 0.1001 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.46997(8) 0.34206(8) 0.44249(5) 0.01797(18) Uani 1 1 d . . . C2 C 0.70933(8) 0.34650(8) 0.29553(5) 0.01600(17) Uani 1 1 d . . . C3 C 0.74546(8) 0.39324(7) 0.41844(5) 0.01396(16) Uani 1 1 d . . . C4 C 0.59345(8) 0.20193(7) 0.41406(5) 0.01570(17) Uani 1 1 d . . . C5 C 0.50677(10) 0.35318(10) 0.51601(6) 0.0242(2) Uani 1 1 d . . . H5A H 0.5228 0.2896 0.5356 0.036 Uiso 1 1 calc R . . H5B H 0.4478 0.3839 0.5378 0.036 Uiso 1 1 calc R . . H5C H 0.5734 0.3932 0.5219 0.036 Uiso 1 1 calc R . . C6 C 0.77353(9) 0.25259(8) 0.29249(6) 0.02072(19) Uani 1 1 d . . . H6A H 0.8279 0.2477 0.3314 0.031 Uiso 1 1 calc R . . H6B H 0.8116 0.2517 0.2523 0.031 Uiso 1 1 calc R . . H6C H 0.7224 0.1980 0.2918 0.031 Uiso 1 1 calc R . . C7 C 0.70312(8) 0.21471(7) 0.44147(5) 0.01448(16) Uani 1 1 d . . . C8 C 0.75620(8) 0.31042(7) 0.45819(5) 0.01414(16) Uani 1 1 d . . . C9 C 0.50561(8) 0.27615(8) 0.39725(5) 0.01586(17) Uani 1 1 d . . . C10 C 0.69604(8) 0.40715(7) 0.34918(5) 0.01459(16) Uani 1 1 d . . . C11 C 0.38616(8) 0.35831(8) 0.32535(5) 0.01721(17) Uani 1 1 d . . . C12 C 0.59522(9) 0.49433(8) 0.27112(5) 0.01629(17) Uani 1 1 d . . . C13 C 0.84815(8) 0.41364(7) 0.52987(5) 0.01448(16) Uani 1 1 d . . . C14 C 0.70651(9) 0.05238(7) 0.43294(5) 0.01603(17) Uani 1 1 d . . . C15 C 0.32428(8) 0.38977(8) 0.26139(5) 0.01854(18) Uani 1 1 d . . . C16 C 0.25161(9) 0.47000(9) 0.25758(6) 0.0211(2) Uani 1 1 d . . . H16 H 0.2401 0.5048 0.2965 0.025 Uiso 1 1 calc R . . C17 C 0.19613(10) 0.49829(10) 0.19580(6) 0.0263(2) Uani 1 1 d . . . H17 H 0.1474 0.5518 0.1936 0.032 Uiso 1 1 calc R . . C18 C 0.21314(10) 0.44711(11) 0.13753(6) 0.0286(3) Uani 1 1 d . . . H18 H 0.1760 0.4664 0.0963 0.034 Uiso 1 1 calc R . . C19 C 0.28567(11) 0.36691(11) 0.14073(6) 0.0284(2) Uani 1 1 d . . . H19 H 0.2973 0.3325 0.1017 0.034 Uiso 1 1 calc R . . C20 C 0.34069(10) 0.33837(10) 0.20244(6) 0.0246(2) Uani 1 1 d . . . H20 H 0.3890 0.2845 0.2046 0.030 Uiso 1 1 calc R . . C21 C 0.51941(9) 0.57104(8) 0.24143(5) 0.01728(17) Uani 1 1 d . . . C22 C 0.47791(10) 0.64149(8) 0.28362(6) 0.0217(2) Uani 1 1 d . . . H22 H 0.5007 0.6406 0.3297 0.026 Uiso 1 1 calc R . . C23 C 0.40301(11) 0.71258(9) 0.25693(7) 0.0281(2) Uani 1 1 d . . . H23 H 0.3761 0.7597 0.2850 0.034 Uiso 1 1 calc R . . C24 C 0.36822(11) 0.71352(10) 0.18836(7) 0.0293(3) Uani 1 1 d . . . H24 H 0.3169 0.7606 0.1707 0.035 Uiso 1 1 calc R . . C25 C 0.40955(11) 0.64473(10) 0.14618(6) 0.0278(2) Uani 1 1 d . . . H25 H 0.3866 0.6460 0.1001 0.033 Uiso 1 1 calc R . . C26 C 0.48528(10) 0.57387(9) 0.17255(6) 0.0233(2) Uani 1 1 d . . . H26 H 0.5134 0.5280 0.1440 0.028 Uiso 1 1 calc R . . C27 C 0.91485(8) 0.44786(8) 0.59153(5) 0.01590(17) Uani 1 1 d . . . C28 C 0.95852(9) 0.37796(9) 0.63824(6) 0.0215(2) Uani 1 1 d . . . H28 H 0.9442 0.3116 0.6300 0.026 Uiso 1 1 calc R . . C29 C 1.02328(10) 0.40648(10) 0.69700(6) 0.0269(2) Uani 1 1 d . . . H29 H 1.0511 0.3595 0.7283 0.032 Uiso 1 1 calc R . . C30 C 1.04635(10) 0.50525(10) 0.70880(6) 0.0272(2) Uani 1 1 d . . . H30 H 1.0905 0.5246 0.7478 0.033 Uiso 1 1 calc R . . C31 C 1.00372(10) 0.57485(10) 0.66264(6) 0.0257(2) Uani 1 1 d . . . H31 H 1.0196 0.6410 0.6707 0.031 Uiso 1 1 calc R . . C32 C 0.93742(9) 0.54730(8) 0.60424(6) 0.02027(19) Uani 1 1 d . . . H32 H 0.9082 0.5948 0.5737 0.024 Uiso 1 1 calc R . . C33 C 0.75242(9) -0.04803(8) 0.43623(5) 0.01797(18) Uani 1 1 d . . . C34 C 0.86580(10) -0.06113(8) 0.45948(6) 0.02063(19) Uani 1 1 d . . . H34 H 0.9096 -0.0070 0.4739 0.025 Uiso 1 1 calc R . . C35 C 0.91396(11) -0.15429(9) 0.46128(6) 0.0254(2) Uani 1 1 d . . . H35 H 0.9897 -0.1626 0.4766 0.030 Uiso 1 1 calc R . . C36 C 0.84813(12) -0.23499(9) 0.43995(7) 0.0304(3) Uani 1 1 d . . . H36 H 0.8797 -0.2976 0.4415 0.036 Uiso 1 1 calc R . . C37 C 0.73566(13) -0.22258(9) 0.41639(8) 0.0336(3) Uani 1 1 d . . . H37 H 0.6923 -0.2768 0.4017 0.040 Uiso 1 1 calc R . . C38 C 0.68720(11) -0.12936(9) 0.41451(7) 0.0272(2) Uani 1 1 d . . . H38 H 0.6116 -0.1213 0.3988 0.033 Uiso 1 1 calc R . . N1 N 0.45714(7) 0.28452(7) 0.33146(5) 0.01727(16) Uani 1 1 d . . . N2 N 0.63277(7) 0.49086(6) 0.33511(4) 0.01567(15) Uani 1 1 d . . . N3 N 0.81631(7) 0.32216(6) 0.52047(4) 0.01572(15) Uani 1 1 d . . . N4 N 0.76581(7) 0.13019(6) 0.45252(4) 0.01565(15) Uani 1 1 d . . . S1 S 0.37229(2) 0.41926(2) 0.400524(13) 0.01956(6) Uani 1 1 d . . . S2 S 0.63722(2) 0.39595(2) 0.224248(13) 0.01804(5) Uani 1 1 d . . . S3 S 0.80746(2) 0.491122(18) 0.462854(12) 0.01538(5) Uani 1 1 d . . . S4 S 0.56898(2) 0.07824(2) 0.400118(14) 0.01880(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0124(4) 0.0243(5) 0.0174(4) -0.0012(4) 0.0023(3) -0.0005(3) C2 0.0133(4) 0.0185(4) 0.0164(4) -0.0007(3) 0.0025(3) 0.0015(3) C3 0.0124(4) 0.0142(4) 0.0154(4) -0.0002(3) 0.0019(3) -0.0005(3) C4 0.0140(4) 0.0160(4) 0.0166(4) -0.0003(3) -0.0006(3) -0.0020(3) C5 0.0215(5) 0.0352(6) 0.0158(4) -0.0033(4) 0.0017(4) 0.0016(4) C6 0.0187(5) 0.0201(5) 0.0236(5) -0.0037(4) 0.0031(4) 0.0045(4) C7 0.0132(4) 0.0144(4) 0.0152(4) 0.0006(3) -0.0012(3) -0.0018(3) C8 0.0115(4) 0.0141(4) 0.0164(4) 0.0000(3) -0.0004(3) -0.0007(3) C9 0.0110(4) 0.0194(4) 0.0168(4) -0.0004(3) -0.0002(3) -0.0012(3) C10 0.0128(4) 0.0157(4) 0.0156(4) 0.0010(3) 0.0033(3) 0.0005(3) C11 0.0119(4) 0.0221(5) 0.0176(4) -0.0013(3) 0.0015(3) 0.0007(3) C12 0.0153(4) 0.0189(4) 0.0152(4) 0.0014(3) 0.0043(3) 0.0031(3) C13 0.0112(4) 0.0153(4) 0.0170(4) -0.0011(3) 0.0015(3) -0.0009(3) C14 0.0166(4) 0.0150(4) 0.0163(4) 0.0001(3) 0.0012(3) -0.0023(3) C15 0.0117(4) 0.0253(5) 0.0183(4) 0.0002(4) 0.0001(3) 0.0020(3) C16 0.0145(4) 0.0287(5) 0.0205(5) 0.0019(4) 0.0034(3) 0.0057(4) C17 0.0174(5) 0.0370(6) 0.0246(5) 0.0057(5) 0.0023(4) 0.0101(4) C18 0.0210(5) 0.0423(7) 0.0218(5) 0.0047(5) -0.0015(4) 0.0078(5) C19 0.0257(5) 0.0388(7) 0.0197(5) -0.0029(5) -0.0027(4) 0.0080(5) C20 0.0216(5) 0.0313(6) 0.0201(5) -0.0026(4) -0.0019(4) 0.0086(4) C21 0.0157(4) 0.0193(4) 0.0171(4) 0.0032(3) 0.0032(3) 0.0023(3) C22 0.0223(5) 0.0223(5) 0.0204(5) -0.0003(4) 0.0008(4) 0.0053(4) C23 0.0293(6) 0.0249(5) 0.0293(6) -0.0023(4) -0.0011(4) 0.0107(5) C24 0.0295(6) 0.0269(6) 0.0304(6) 0.0048(5) -0.0023(5) 0.0099(5) C25 0.0308(6) 0.0323(6) 0.0200(5) 0.0061(4) 0.0007(4) 0.0089(5) C26 0.0245(5) 0.0289(6) 0.0169(4) 0.0028(4) 0.0037(4) 0.0080(4) C27 0.0110(4) 0.0190(4) 0.0179(4) -0.0041(3) 0.0028(3) -0.0026(3) C28 0.0198(5) 0.0232(5) 0.0205(5) -0.0016(4) -0.0022(4) -0.0028(4) C29 0.0226(5) 0.0342(6) 0.0225(5) -0.0024(4) -0.0051(4) -0.0025(4) C30 0.0190(5) 0.0402(7) 0.0221(5) -0.0109(5) 0.0007(4) -0.0080(5) C31 0.0208(5) 0.0288(6) 0.0279(6) -0.0121(4) 0.0047(4) -0.0090(4) C32 0.0170(4) 0.0201(5) 0.0240(5) -0.0059(4) 0.0036(4) -0.0036(4) C33 0.0220(5) 0.0144(4) 0.0181(4) 0.0005(3) 0.0049(3) -0.0019(3) C34 0.0251(5) 0.0171(4) 0.0194(4) 0.0007(4) 0.0007(4) 0.0015(4) C35 0.0313(6) 0.0206(5) 0.0248(5) 0.0042(4) 0.0066(4) 0.0066(4) C36 0.0406(7) 0.0151(5) 0.0385(7) 0.0048(4) 0.0190(6) 0.0032(5) C37 0.0380(7) 0.0160(5) 0.0498(8) -0.0031(5) 0.0190(6) -0.0072(5) C38 0.0259(6) 0.0181(5) 0.0390(7) -0.0031(4) 0.0096(5) -0.0059(4) N1 0.0125(3) 0.0213(4) 0.0174(4) -0.0011(3) -0.0008(3) 0.0007(3) N2 0.0149(4) 0.0165(4) 0.0161(3) 0.0011(3) 0.0040(3) 0.0022(3) N3 0.0135(3) 0.0156(4) 0.0174(4) -0.0005(3) -0.0018(3) -0.0011(3) N4 0.0162(4) 0.0135(3) 0.0166(4) 0.0010(3) -0.0012(3) -0.0014(3) S1 0.01384(11) 0.02652(13) 0.01844(11) -0.00306(9) 0.00229(8) 0.00427(9) S2 0.01732(11) 0.02296(12) 0.01420(10) -0.00074(8) 0.00334(8) 0.00409(9) S3 0.01686(11) 0.01300(10) 0.01670(10) -0.00082(8) 0.00379(8) -0.00170(8) S4 0.01526(11) 0.01751(11) 0.02290(12) -0.00197(9) -0.00153(8) -0.00471(8) _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 C9 1.3691(15) . ? C1 C5 1.4919(15) . ? C1 S1 1.7195(11) . ? C2 C10 1.3715(14) . ? C2 C6 1.4934(15) . ? C2 S2 1.7188(10) . ? C3 C8 1.3747(14) . ? C3 C10 1.4550(14) . ? C3 S3 1.7220(10) . ? C4 C7 1.3757(13) . ? C4 C9 1.4684(14) . ? C4 S4 1.7246(10) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N4 1.3764(13) . ? C7 C8 1.4703(13) . ? C8 N3 1.3762(13) . ? C9 N1 1.3808(13) . ? C10 N2 1.3786(13) . ? C11 N1 1.3105(13) . ? C11 C15 1.4682(15) . ? C11 S1 1.7336(11) . ? C12 N2 1.3070(13) . ? C12 C21 1.4646(14) . ? C12 S2 1.7343(11) . ? C13 N3 1.3084(13) . ? C13 C27 1.4680(14) . ? C13 S3 1.7297(10) . ? C14 N4 1.3095(13) . ? C14 C33 1.4700(15) . ? C14 S4 1.7382(11) . ? C15 C16 1.3907(15) . ? C15 C20 1.3970(16) . ? C16 C17 1.3895(16) . ? C16 H16 0.9300 . ? C17 C18 1.3857(18) . ? C17 H17 0.9300 . ? C18 C19 1.3895(18) . ? C18 H18 0.9300 . ? C19 C20 1.3873(16) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? C21 C26 1.3903(15) . ? C21 C22 1.3980(15) . ? C22 C23 1.3846(16) . ? C22 H22 0.9300 . ? C23 C24 1.3853(19) . ? C23 H23 0.9300 . ? C24 C25 1.3816(19) . ? C24 H24 0.9300 . ? C25 C26 1.3864(16) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C28 1.3927(16) . ? C27 C32 1.3966(15) . ? C28 C29 1.3889(16) . ? C28 H28 0.9300 . ? C29 C30 1.3862(18) . ? C29 H29 0.9300 . ? C30 C31 1.379(2) . ? C30 H30 0.9300 . ? C31 C32 1.3885(16) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 C38 1.3950(16) . ? C33 C34 1.3951(16) . ? C34 C35 1.3899(16) . ? C34 H34 0.9300 . ? C35 C36 1.3901(19) . ? C35 H35 0.9300 . ? C36 C37 1.385(2) . ? C36 H36 0.9300 . ? C37 C38 1.3920(18) . ? C37 H37 0.9300 . ? C38 H38 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 C9 C1 C5 129.19(10) . . ? C9 C1 S1 108.72(8) . . ? C5 C1 S1 122.06(8) . . ? C10 C2 C6 130.29(9) . . ? C10 C2 S2 108.63(7) . . ? C6 C2 S2 121.07(8) . . ? C8 C3 C10 131.04(9) . . ? C8 C3 S3 109.15(7) . . ? C10 C3 S3 119.78(7) . . ? C7 C4 C9 129.11(9) . . ? C7 C4 S4 108.98(8) . . ? C9 C4 S4 121.91(7) . . ? C1 C5 H5A 109.5 . . ? C1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C2 C6 H6A 109.5 . . ? C2 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C2 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C4 C7 N4 115.90(9) . . ? C4 C7 C8 124.84(9) . . ? N4 C7 C8 119.26(8) . . ? C3 C8 N3 115.63(9) . . ? C3 C8 C7 125.63(9) . . ? N3 C8 C7 118.60(9) . . ? C1 C9 N1 116.23(9) . . ? C1 C9 C4 124.25(9) . . ? N1 C9 C4 119.46(9) . . ? C2 C10 N2 116.31(9) . . ? C2 C10 C3 126.29(9) . . ? N2 C10 C3 117.37(9) . . ? N1 C11 C15 124.46(9) . . ? N1 C11 S1 113.85(8) . . ? C15 C11 S1 121.69(8) . . ? N2 C12 C21 123.65(9) . . ? N2 C12 S2 114.07(8) . . ? C21 C12 S2 122.20(8) . . ? N3 C13 C27 123.03(9) . . ? N3 C13 S3 114.49(7) . . ? C27 C13 S3 122.46(8) . . ? N4 C14 C33 123.35(9) . . ? N4 C14 S4 114.11(8) . . ? C33 C14 S4 122.52(8) . . ? C16 C15 C20 119.17(10) . . ? C16 C15 C11 122.04(10) . . ? C20 C15 C11 118.77(10) . . ? C17 C16 C15 120.17(11) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C18 C17 C16 120.30(11) . . ? C18 C17 H17 119.8 . . ? C16 C17 H17 119.8 . . ? C17 C18 C19 120.01(11) . . ? C17 C18 H18 120.0 . . ? C19 C18 H18 120.0 . . ? C20 C19 C18 119.71(12) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C15 120.63(11) . . ? C19 C20 H20 119.7 . . ? C15 C20 H20 119.7 . . ? C26 C21 C22 119.21(10) . . ? C26 C21 C12 121.57(10) . . ? C22 C21 C12 119.20(9) . . ? C23 C22 C21 120.15(11) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.03(11) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C25 C24 C23 120.22(11) . . ? C25 C24 H24 119.9 . . ? C23 C24 H24 119.9 . . ? C24 C25 C26 120.00(11) . . ? C24 C25 H25 120.0 . . ? C26 C25 H25 120.0 . . ? C25 C26 C21 120.38(11) . . ? C25 C26 H26 119.8 . . ? C21 C26 H26 119.8 . . ? C28 C27 C32 119.20(10) . . ? C28 C27 C13 118.38(9) . . ? C32 C27 C13 122.41(10) . . ? C29 C28 C27 120.61(11) . . ? C29 C28 H28 119.7 . . ? C27 C28 H28 119.7 . . ? C30 C29 C28 119.78(12) . . ? C30 C29 H29 120.1 . . ? C28 C29 H29 120.1 . . ? C31 C30 C29 119.92(11) . . ? C31 C30 H30 120.0 . . ? C29 C30 H30 120.0 . . ? C30 C31 C32 120.78(11) . . ? C30 C31 H31 119.6 . . ? C32 C31 H31 119.6 . . ? C31 C32 C27 119.70(11) . . ? C31 C32 H32 120.2 . . ? C27 C32 H32 120.2 . . ? C38 C33 C34 119.49(10) . . ? C38 C33 C14 121.94(10) . . ? C34 C33 C14 118.52(9) . . ? C35 C34 C33 120.60(11) . . ? C35 C34 H34 119.7 . . ? C33 C34 H34 119.7 . . ? C34 C35 C36 119.50(12) . . ? C34 C35 H35 120.2 . . ? C36 C35 H35 120.2 . . ? C37 C36 C35 120.28(11) . . ? C37 C36 H36 119.9 . . ? C35 C36 H36 119.9 . . ? C36 C37 C38 120.34(12) . . ? C36 C37 H37 119.8 . . ? C38 C37 H37 119.8 . . ? C37 C38 C33 119.78(12) . . ? C37 C38 H38 120.1 . . ? C33 C38 H38 120.1 . . ? C11 N1 C9 110.76(9) . . ? C12 N2 C10 110.68(9) . . ? C13 N3 C8 110.84(9) . . ? C14 N4 C7 111.05(8) . . ? C1 S1 C11 90.42(5) . . ? C2 S2 C12 90.30(5) . . ? C3 S3 C13 89.82(5) . . ? C4 S4 C14 89.96(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 C9 C4 C7 N4 179.14(10) . . . . ? S4 C4 C7 N4 -1.16(11) . . . . ? C9 C4 C7 C8 -1.82(17) . . . . ? S4 C4 C7 C8 177.88(8) . . . . ? C10 C3 C8 N3 174.92(10) . . . . ? S3 C3 C8 N3 -3.08(11) . . . . ? C10 C3 C8 C7 -9.47(17) . . . . ? S3 C3 C8 C7 172.53(8) . . . . ? C4 C7 C8 C3 -43.25(16) . . . . ? N4 C7 C8 C3 135.76(10) . . . . ? C4 C7 C8 N3 132.24(11) . . . . ? N4 C7 C8 N3 -48.75(13) . . . . ? C5 C1 C9 N1 -178.97(11) . . . . ? S1 C1 C9 N1 -0.75(12) . . . . ? C5 C1 C9 C4 -1.54(18) . . . . ? S1 C1 C9 C4 176.68(8) . . . . ? C7 C4 C9 C1 -56.78(16) . . . . ? S4 C4 C9 C1 123.56(10) . . . . ? C7 C4 C9 N1 120.57(12) . . . . ? S4 C4 C9 N1 -59.09(12) . . . . ? C6 C2 C10 N2 178.56(10) . . . . ? S2 C2 C10 N2 -0.93(11) . . . . ? C6 C2 C10 C3 0.93(18) . . . . ? S2 C2 C10 C3 -178.56(8) . . . . ? C8 C3 C10 C2 -43.06(17) . . . . ? S3 C3 C10 C2 134.76(10) . . . . ? C8 C3 C10 N2 139.33(11) . . . . ? S3 C3 C10 N2 -42.85(12) . . . . ? N1 C11 C15 C16 -178.64(11) . . . . ? S1 C11 C15 C16 0.14(15) . . . . ? N1 C11 C15 C20 0.20(17) . . . . ? S1 C11 C15 C20 178.98(9) . . . . ? C20 C15 C16 C17 0.07(18) . . . . ? C11 C15 C16 C17 178.91(11) . . . . ? C15 C16 C17 C18 -0.28(19) . . . . ? C16 C17 C18 C19 0.2(2) . . . . ? C17 C18 C19 C20 0.1(2) . . . . ? C18 C19 C20 C15 -0.3(2) . . . . ? C16 C15 C20 C19 0.21(19) . . . . ? C11 C15 C20 C19 -178.67(12) . . . . ? N2 C12 C21 C26 177.38(11) . . . . ? S2 C12 C21 C26 -6.02(15) . . . . ? N2 C12 C21 C22 -4.41(16) . . . . ? S2 C12 C21 C22 172.19(9) . . . . ? C26 C21 C22 C23 0.53(18) . . . . ? C12 C21 C22 C23 -177.72(11) . . . . ? C21 C22 C23 C24 0.6(2) . . . . ? C22 C23 C24 C25 -1.2(2) . . . . ? C23 C24 C25 C26 0.6(2) . . . . ? C24 C25 C26 C21 0.5(2) . . . . ? C22 C21 C26 C25 -1.07(18) . . . . ? C12 C21 C26 C25 177.15(11) . . . . ? N3 C13 C27 C28 8.57(15) . . . . ? S3 C13 C27 C28 -170.18(8) . . . . ? N3 C13 C27 C32 -172.55(10) . . . . ? S3 C13 C27 C32 8.69(14) . . . . ? C32 C27 C28 C29 0.33(17) . . . . ? C13 C27 C28 C29 179.25(10) . . . . ? C27 C28 C29 C30 -1.10(19) . . . . ? C28 C29 C30 C31 0.86(19) . . . . ? C29 C30 C31 C32 0.15(19) . . . . ? C30 C31 C32 C27 -0.91(17) . . . . ? C28 C27 C32 C31 0.67(16) . . . . ? C13 C27 C32 C31 -178.20(10) . . . . ? N4 C14 C33 C38 -179.53(11) . . . . ? S4 C14 C33 C38 -1.52(15) . . . . ? N4 C14 C33 C34 -1.98(15) . . . . ? S4 C14 C33 C34 176.03(8) . . . . ? C38 C33 C34 C35 -0.15(17) . . . . ? C14 C33 C34 C35 -177.76(10) . . . . ? C33 C34 C35 C36 -0.27(17) . . . . ? C34 C35 C36 C37 0.69(19) . . . . ? C35 C36 C37 C38 -0.7(2) . . . . ? C36 C37 C38 C33 0.2(2) . . . . ? C34 C33 C38 C37 0.16(18) . . . . ? C14 C33 C38 C37 177.69(12) . . . . ? C15 C11 N1 C9 177.20(10) . . . . ? S1 C11 N1 C9 -1.66(11) . . . . ? C1 C9 N1 C11 1.58(13) . . . . ? C4 C9 N1 C11 -175.98(9) . . . . ? C21 C12 N2 C10 175.91(9) . . . . ? S2 C12 N2 C10 -0.94(11) . . . . ? C2 C10 N2 C12 1.23(13) . . . . ? C3 C10 N2 C12 179.08(9) . . . . ? C27 C13 N3 C8 -179.27(9) . . . . ? S3 C13 N3 C8 -0.43(11) . . . . ? C3 C8 N3 C13 2.32(12) . . . . ? C7 C8 N3 C13 -173.62(9) . . . . ? C33 C14 N4 C7 177.73(9) . . . . ? S4 C14 N4 C7 -0.44(11) . . . . ? C4 C7 N4 C14 1.05(13) . . . . ? C8 C7 N4 C14 -178.04(9) . . . . ? C9 C1 S1 C11 -0.17(8) . . . . ? C5 C1 S1 C11 178.21(10) . . . . ? N1 C11 S1 C1 1.09(9) . . . . ? C15 C11 S1 C1 -177.81(9) . . . . ? C10 C2 S2 C12 0.31(8) . . . . ? C6 C2 S2 C12 -179.24(9) . . . . ? N2 C12 S2 C2 0.37(9) . . . . ? C21 C12 S2 C2 -176.53(9) . . . . ? C8 C3 S3 C13 2.26(8) . . . . ? C10 C3 S3 C13 -176.00(8) . . . . ? N3 C13 S3 C3 -1.10(8) . . . . ? C27 C13 S3 C3 177.75(8) . . . . ? C7 C4 S4 C14 0.72(8) . . . . ? C9 C4 S4 C14 -179.55(9) . . . . ? N4 C14 S4 C4 -0.17(8) . . . . ? C33 C14 S4 C4 -178.36(9) . . . . ? _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.670 _refine_diff_density_min -0.373 _refine_diff_density_rms 0.073