# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email thai@chem.umass.edu _publ_contact_author_name 'Sankaran Thayumanavan' loop_ _publ_author_name 'Ganapathy Balaji' 'Andrea Della Pelle' 'Bhooshan Popere' 'Annamalai Chandrasekaran' 'Sankaran Thayumanavan' data_bg4 _database_code_depnum_ccdc_archive 'CCDC 864076' #TrackingRef '- Compound 7.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H25 N S2' _chemical_formula_weight 391.57 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' 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 8.7411(2) _cell_length_b 10.8404(2) _cell_length_c 11.3321(2) _cell_angle_alpha 94.6197(10) _cell_angle_beta 106.9013(11) _cell_angle_gamma 91.5749(12) _cell_volume 1022.62(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.269 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius KappaCCD area detector' _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 6095 _diffrn_reflns_av_R_equivalents 0.0168 _diffrn_reflns_av_sigmaI/netI 0.0256 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 4.38 _diffrn_reflns_theta_max 25.06 _reflns_number_total 3458 _reflns_number_gt 3252 _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. The alkyl chain was disordered over two orientations and it was refined with 64:36 occupancy ratio. None of the hydrogens on the alkyl chain could be included in the calculations. These 17 unaccounted hydrogens led to a higher R-factor, but the remainder of the molecule is well-behaved. ; _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^)+(0.1021P)^2^+1.1905P] 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 3458 _refine_ls_number_parameters 240 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0717 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.2003 _refine_ls_wR_factor_gt 0.1981 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.07040(9) 0.62284(7) 0.60738(8) 0.0468(3) Uani 1 1 d . . . S2 S 0.29554(9) 0.30368(7) 0.57407(7) 0.0460(3) Uani 1 1 d . . . N1 N 0.5286(3) 0.6163(2) 0.6916(2) 0.0385(6) Uani 1 1 d . . . C1 C 0.1504(4) 0.7748(3) 0.6563(3) 0.0468(7) Uani 1 1 d . . . C2 C 0.0606(4) 0.8784(3) 0.6592(4) 0.0622(10) Uani 1 1 d . . . H2 H -0.0506 0.8705 0.6346 0.075 Uiso 1 1 calc R . . C3 C 0.1391(5) 0.9927(4) 0.6989(4) 0.0725(12) Uani 1 1 d . . . H3 H 0.0802 1.0625 0.7013 0.087 Uiso 1 1 calc R . . C4 C 0.3054(5) 1.0052(3) 0.7355(4) 0.0654(10) Uani 1 1 d . . . H4 H 0.3564 1.0833 0.7618 0.079 Uiso 1 1 calc R . . C5 C 0.3962(4) 0.9022(3) 0.7333(3) 0.0528(8) Uani 1 1 d . . . H5 H 0.5074 0.9113 0.7589 0.063 Uiso 1 1 calc R . . C6 C 0.3200(4) 0.7856(3) 0.6925(3) 0.0422(7) Uani 1 1 d . . . C7 C 0.3798(3) 0.6647(3) 0.6769(3) 0.0389(6) Uani 1 1 d . . . C8 C 0.2618(3) 0.5707(3) 0.6325(3) 0.0380(6) Uani 1 1 d . . . C9 C 0.3393(3) 0.4602(3) 0.6184(3) 0.0376(6) Uani 1 1 d . . . C10 C 0.5021(3) 0.4909(3) 0.6559(3) 0.0377(6) Uani 1 1 d . . . C11 C 0.6005(4) 0.3874(3) 0.6487(3) 0.0411(7) Uani 1 1 d . . . C12 C 0.7658(4) 0.3784(3) 0.6736(3) 0.0512(8) Uani 1 1 d . . . H12 H 0.8342 0.4487 0.7023 0.061 Uiso 1 1 calc R . . C13 C 0.8270(4) 0.2648(4) 0.6556(4) 0.0612(9) Uani 1 1 d . . . H13 H 0.9370 0.2591 0.6717 0.073 Uiso 1 1 calc R . . C14 C 0.7268(5) 0.1590(4) 0.6138(4) 0.0667(10) Uani 1 1 d . . . H14 H 0.7706 0.0833 0.6023 0.080 Uiso 1 1 calc R . . C15 C 0.5626(5) 0.1644(3) 0.5888(3) 0.0583(9) Uani 1 1 d . . . H15 H 0.4953 0.0934 0.5615 0.070 Uiso 1 1 calc R . . C16 C 0.5011(4) 0.2795(3) 0.6057(3) 0.0447(7) Uani 1 1 d . . . C17 C 0.6839(4) 0.6821(3) 0.7545(3) 0.0476(8) Uani 1 1 d . . . C18 C 0.7096(7) 0.7071(5) 0.8965(5) 0.0512(15) Uiso 0.637(8) 1 d P . . C19 C 0.8583(8) 0.7957(6) 0.9548(6) 0.0647(18) Uiso 0.637(8) 1 d P . . C20 C 1.0162(6) 0.7475(6) 0.9636(5) 0.0916(15) Uani 1 1 d . . . C21 C 1.1547(11) 0.8430(9) 1.0166(8) 0.084(2) Uiso 0.637(8) 1 d P . . C22 C 1.3204(14) 0.7784(11) 1.0320(9) 0.105(3) Uiso 0.637(8) 1 d P . . C23 C 0.7117(8) 0.5859(6) 0.9531(6) 0.0667(18) Uiso 0.637(8) 1 d P . . C24 C 0.7160(8) 0.6134(8) 1.0940(4) 0.121(2) Uani 1 1 d . . . C18A C 0.7591(13) 0.6319(10) 0.8877(9) 0.056(3) Uiso 0.363(8) 1 d P . . C19A C 0.945(2) 0.6466(18) 0.9395(16) 0.107(5) Uiso 0.363(8) 1 d P . . C21A C 1.195(2) 0.7721(18) 1.0029(16) 0.098(5) Uiso 0.363(8) 1 d P . . C22A C 1.292(3) 0.867(2) 1.0321(18) 0.119(6) Uiso 0.363(8) 1 d P . . C23A C 0.6559(15) 0.6843(11) 0.9664(11) 0.070(3) Uiso 0.363(8) 1 d P . . 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 0.0339(4) 0.0403(5) 0.0626(5) -0.0025(3) 0.0104(3) 0.0033(3) S2 0.0421(5) 0.0373(5) 0.0544(5) -0.0036(3) 0.0096(3) 0.0026(3) N1 0.0309(12) 0.0391(13) 0.0424(13) 0.0046(10) 0.0058(10) 0.0005(10) C1 0.0428(16) 0.0398(16) 0.0529(17) 0.0008(13) 0.0071(13) 0.0050(13) C2 0.0477(19) 0.0473(19) 0.083(3) -0.0044(17) 0.0071(17) 0.0129(15) C3 0.063(2) 0.0413(19) 0.100(3) -0.0031(19) 0.005(2) 0.0177(17) C4 0.067(2) 0.0364(18) 0.083(3) 0.0003(17) 0.008(2) 0.0028(16) C5 0.0481(18) 0.0408(17) 0.062(2) 0.0039(14) 0.0046(15) 0.0000(14) C6 0.0410(16) 0.0384(16) 0.0444(15) 0.0046(12) 0.0079(12) 0.0045(12) C7 0.0360(15) 0.0378(15) 0.0413(15) 0.0061(12) 0.0081(12) 0.0042(12) C8 0.0343(14) 0.0371(15) 0.0415(15) 0.0034(11) 0.0092(12) 0.0027(11) C9 0.0371(14) 0.0351(15) 0.0389(14) 0.0029(11) 0.0087(11) 0.0034(11) C10 0.0360(15) 0.0404(15) 0.0362(14) 0.0060(11) 0.0088(11) 0.0056(12) C11 0.0436(16) 0.0444(16) 0.0360(14) 0.0061(12) 0.0113(12) 0.0111(13) C12 0.0427(17) 0.057(2) 0.0532(18) 0.0079(15) 0.0117(14) 0.0121(14) C13 0.0488(19) 0.068(2) 0.066(2) 0.0061(18) 0.0150(16) 0.0240(17) C14 0.065(2) 0.061(2) 0.072(2) -0.0015(18) 0.0169(19) 0.0297(19) C15 0.062(2) 0.0491(19) 0.061(2) -0.0048(15) 0.0148(17) 0.0139(16) C16 0.0471(17) 0.0451(17) 0.0411(15) 0.0026(12) 0.0114(13) 0.0112(13) C17 0.0353(15) 0.0579(19) 0.0443(16) 0.0027(14) 0.0051(12) -0.0091(13) C20 0.071(3) 0.111(4) 0.083(3) 0.004(3) 0.011(2) -0.023(3) C24 0.131(5) 0.177(7) 0.046(2) 0.020(3) 0.014(3) -0.033(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C8 1.732(3) . ? S1 C1 1.753(3) . ? S2 C9 1.730(3) . ? S2 C16 1.759(3) . ? N1 C10 1.379(4) . ? N1 C7 1.385(4) . ? N1 C17 1.471(4) . ? C1 C2 1.391(5) . ? C1 C6 1.417(4) . ? C2 C3 1.376(5) . ? C2 H2 0.9300 . ? C3 C4 1.390(6) . ? C3 H3 0.9300 . ? C4 C5 1.390(5) . ? C4 H4 0.9300 . ? C5 C6 1.391(4) . ? C5 H5 0.9300 . ? C6 C7 1.442(4) . ? C7 C8 1.384(4) . ? C8 C9 1.413(4) . ? C9 C10 1.384(4) . ? C10 C11 1.444(4) . ? C11 C12 1.397(4) . ? C11 C16 1.403(5) . ? C12 C13 1.380(5) . ? C12 H12 0.9300 . ? C13 C14 1.387(6) . ? C13 H13 0.9300 . ? C14 C15 1.384(5) . ? C14 H14 0.9300 . ? C15 C16 1.392(5) . ? C15 H15 0.9300 . ? C17 C18 1.558(6) . ? C17 C18A 1.607(10) . ? C18 C23 1.506(9) . ? C18 C19 1.543(8) . ? C19 C20 1.468(8) . ? C20 C19A 1.213(19) . ? C20 C21A 1.506(19) . ? C20 C21 1.519(10) . ? C21 C22 1.596(15) . ? C23 C24 1.590(8) . ? C24 C23A 1.648(13) . ? C18A C23A 1.532(16) . ? C18A C19A 1.56(2) . ? C21A C22A 1.27(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 S1 C1 90.17(14) . . ? C9 S2 C16 89.98(14) . . ? C10 N1 C7 106.9(2) . . ? C10 N1 C17 126.6(3) . . ? C7 N1 C17 125.7(3) . . ? C2 C1 C6 121.1(3) . . ? C2 C1 S1 125.0(3) . . ? C6 C1 S1 113.9(2) . . ? C3 C2 C1 118.9(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C2 C3 C4 120.8(3) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 120.7(3) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.7(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 118.7(3) . . ? C5 C6 C7 132.5(3) . . ? C1 C6 C7 108.8(3) . . ? C8 C7 N1 109.4(3) . . ? C8 C7 C6 114.2(3) . . ? N1 C7 C6 136.3(3) . . ? C7 C8 C9 107.1(3) . . ? C7 C8 S1 112.9(2) . . ? C9 C8 S1 139.9(2) . . ? C10 C9 C8 106.8(3) . . ? C10 C9 S2 112.8(2) . . ? C8 C9 S2 140.4(2) . . ? N1 C10 C9 109.8(2) . . ? N1 C10 C11 136.0(3) . . ? C9 C10 C11 114.2(3) . . ? C12 C11 C16 118.5(3) . . ? C12 C11 C10 132.5(3) . . ? C16 C11 C10 108.9(3) . . ? C13 C12 C11 119.6(3) . . ? C13 C12 H12 120.2 . . ? C11 C12 H12 120.2 . . ? C12 C13 C14 120.9(3) . . ? C12 C13 H13 119.5 . . ? C14 C13 H13 119.5 . . ? C15 C14 C13 120.9(3) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C16 117.9(4) . . ? C14 C15 H15 121.0 . . ? C16 C15 H15 121.0 . . ? C15 C16 C11 122.0(3) . . ? C15 C16 S2 123.9(3) . . ? C11 C16 S2 114.1(2) . . ? N1 C17 C18 111.5(3) . . ? N1 C17 C18A 109.8(4) . . ? C18 C17 C18A 34.7(4) . . ? C23 C18 C19 115.3(5) . . ? C23 C18 C17 109.8(4) . . ? C19 C18 C17 109.7(4) . . ? C20 C19 C18 117.8(5) . . ? C19A C20 C19 85.1(10) . . ? C19A C20 C21A 126.2(13) . . ? C19 C20 C21A 147.7(9) . . ? C19A C20 C21 158.3(11) . . ? C19 C20 C21 114.1(6) . . ? C21A C20 C21 33.7(7) . . ? C20 C21 C22 109.8(8) . . ? C18 C23 C24 108.8(5) . . ? C23 C24 C23A 43.5(5) . . ? C23A C18A C19A 119.7(10) . . ? C23A C18A C17 104.5(8) . . ? C19A C18A C17 115.3(9) . . ? C20 C19A C18A 121.9(15) . . ? C22A C21A C20 136(2) . . ? C18A C23A C24 103.4(9) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 S1 C1 C2 178.4(3) . . . . ? C8 S1 C1 C6 -0.6(3) . . . . ? C6 C1 C2 C3 -0.5(6) . . . . ? S1 C1 C2 C3 -179.5(3) . . . . ? C1 C2 C3 C4 0.1(7) . . . . ? C2 C3 C4 C5 -0.3(7) . . . . ? C3 C4 C5 C6 0.8(6) . . . . ? C4 C5 C6 C1 -1.2(5) . . . . ? C4 C5 C6 C7 178.2(3) . . . . ? C2 C1 C6 C5 1.1(5) . . . . ? S1 C1 C6 C5 -179.9(2) . . . . ? C2 C1 C6 C7 -178.4(3) . . . . ? S1 C1 C6 C7 0.6(3) . . . . ? C10 N1 C7 C8 0.1(3) . . . . ? C17 N1 C7 C8 -169.9(3) . . . . ? C10 N1 C7 C6 -177.7(3) . . . . ? C17 N1 C7 C6 12.3(5) . . . . ? C5 C6 C7 C8 -179.7(3) . . . . ? C1 C6 C7 C8 -0.3(4) . . . . ? C5 C6 C7 N1 -2.0(6) . . . . ? C1 C6 C7 N1 177.4(3) . . . . ? N1 C7 C8 C9 -0.4(3) . . . . ? C6 C7 C8 C9 177.9(2) . . . . ? N1 C7 C8 S1 -178.52(19) . . . . ? C6 C7 C8 S1 -0.2(3) . . . . ? C1 S1 C8 C7 0.5(2) . . . . ? C1 S1 C8 C9 -176.7(4) . . . . ? C7 C8 C9 C10 0.6(3) . . . . ? S1 C8 C9 C10 177.9(3) . . . . ? C7 C8 C9 S2 178.4(3) . . . . ? S1 C8 C9 S2 -4.3(6) . . . . ? C16 S2 C9 C10 -0.4(2) . . . . ? C16 S2 C9 C8 -178.2(4) . . . . ? C7 N1 C10 C9 0.3(3) . . . . ? C17 N1 C10 C9 170.2(3) . . . . ? C7 N1 C10 C11 -179.5(3) . . . . ? C17 N1 C10 C11 -9.7(5) . . . . ? C8 C9 C10 N1 -0.6(3) . . . . ? S2 C9 C10 N1 -179.06(18) . . . . ? C8 C9 C10 C11 179.3(2) . . . . ? S2 C9 C10 C11 0.8(3) . . . . ? N1 C10 C11 C12 -2.2(6) . . . . ? C9 C10 C11 C12 178.0(3) . . . . ? N1 C10 C11 C16 179.0(3) . . . . ? C9 C10 C11 C16 -0.8(4) . . . . ? C16 C11 C12 C13 0.0(5) . . . . ? C10 C11 C12 C13 -178.6(3) . . . . ? C11 C12 C13 C14 -0.5(5) . . . . ? C12 C13 C14 C15 0.1(6) . . . . ? C13 C14 C15 C16 0.7(6) . . . . ? C14 C15 C16 C11 -1.1(5) . . . . ? C14 C15 C16 S2 178.1(3) . . . . ? C12 C11 C16 C15 0.8(5) . . . . ? C10 C11 C16 C15 179.7(3) . . . . ? C12 C11 C16 S2 -178.5(2) . . . . ? C10 C11 C16 S2 0.5(3) . . . . ? C9 S2 C16 C15 -179.3(3) . . . . ? C9 S2 C16 C11 0.0(2) . . . . ? C10 N1 C17 C18 -99.8(4) . . . . ? C7 N1 C17 C18 68.2(4) . . . . ? C10 N1 C17 C18A -62.6(5) . . . . ? C7 N1 C17 C18A 105.4(5) . . . . ? N1 C17 C18 C23 62.3(5) . . . . ? C18A C17 C18 C23 -31.6(7) . . . . ? N1 C17 C18 C19 -170.0(4) . . . . ? C18A C17 C18 C19 96.0(8) . . . . ? C23 C18 C19 C20 53.7(7) . . . . ? C17 C18 C19 C20 -70.9(6) . . . . ? C18 C19 C20 C19A -13.2(10) . . . . ? C18 C19 C20 C21A 179.8(13) . . . . ? C18 C19 C20 C21 177.3(5) . . . . ? C19A C20 C21 C22 25(3) . . . . ? C19 C20 C21 C22 175.6(6) . . . . ? C21A C20 C21 C22 -2.0(12) . . . . ? C19 C18 C23 C24 62.5(7) . . . . ? C17 C18 C23 C24 -173.0(4) . . . . ? C18 C23 C24 C23A 24.5(7) . . . . ? N1 C17 C18A C23A -72.2(8) . . . . ? C18 C17 C18A C23A 27.3(7) . . . . ? N1 C17 C18A C19A 154.4(9) . . . . ? C18 C17 C18A C19A -106.1(13) . . . . ? C19 C20 C19A C18A 14.4(14) . . . . ? C21A C20 C19A C18A -174.1(11) . . . . ? C21 C20 C19A C18A 167.6(17) . . . . ? C23A C18A C19A C20 -62.6(19) . . . . ? C17 C18A C19A C20 63.3(18) . . . . ? C19A C20 C21A C22A -180(2) . . . . ? C19 C20 C21A C22A -16(3) . . . . ? C21 C20 C21A C22A -11.7(16) . . . . ? C19A C18A C23A C24 -58.0(13) . . . . ? C17 C18A C23A C24 171.1(6) . . . . ? C23 C24 C23A C18A -25.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.466 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.057 # Attachment '- Compound 14.txt' data_bg7 _database_code_depnum_ccdc_archive 'CCDC 864077' #TrackingRef '- Compound 14.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H47 N3 O4 S2' _chemical_formula_weight 745.97 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.9704(4) _cell_length_b 12.7453(4) _cell_length_c 15.4994(6) _cell_angle_alpha 108.851(2) _cell_angle_beta 97.4139(18) _cell_angle_gamma 100.602(2) _cell_volume 1974.07(12) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.75 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.255 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 792 _exptl_absorpt_coefficient_mu 0.181 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Nonius KappaCCD area detector' _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 10922 _diffrn_reflns_av_R_equivalents 0.0249 _diffrn_reflns_av_sigmaI/netI 0.0430 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 4.13 _diffrn_reflns_theta_max 25.07 _reflns_number_total 6883 _reflns_number_gt 5201 _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. One methylene carbon on the side-chain was disordered. It was refined in two positions with 0.67:0.33 occupancy ratio. None of the hydrogens on and adjacent to this disordered carbon were included in the calculations. ; _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^)+(0.0808P)^2^+0.9912P] 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 6883 _refine_ls_number_parameters 477 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0779 _refine_ls_R_factor_gt 0.0564 _refine_ls_wR_factor_ref 0.1643 _refine_ls_wR_factor_gt 0.1501 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.095 _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 0.61428(8) 0.07783(6) -0.05361(5) 0.0525(2) Uani 1 1 d . . . C2 C 0.6331(3) 0.0898(2) -0.16078(19) 0.0458(6) Uani 1 1 d . . . C3 C 0.6992(3) 0.0294(2) -0.22211(19) 0.0458(6) Uani 1 1 d . . . N4 N 0.7653(2) -0.0501(2) -0.21401(16) 0.0516(6) Uani 1 1 d . . . H4 H 0.7742 -0.0728 -0.1675 0.062 Uiso 1 1 calc R . . C5 C 0.8149(3) -0.0872(2) -0.2926(2) 0.0492(7) Uani 1 1 d . . . C6 C 0.8881(3) -0.1670(3) -0.3150(2) 0.0607(8) Uani 1 1 d . . . H6 H 0.9104 -0.2040 -0.2748 0.073 Uiso 1 1 calc R . . C7 C 0.9261(3) -0.1888(3) -0.3987(2) 0.0688(9) Uani 1 1 d . . . H7 H 0.9750 -0.2417 -0.4152 0.083 Uiso 1 1 calc R . . C8 C 0.8938(4) -0.1343(3) -0.4591(2) 0.0727(9) Uani 1 1 d . . . H8 H 0.9218 -0.1509 -0.5150 0.087 Uiso 1 1 calc R . . C9 C 0.8204(3) -0.0556(3) -0.4381(2) 0.0611(8) Uani 1 1 d . . . H9 H 0.7986 -0.0197 -0.4794 0.073 Uiso 1 1 calc R . . C10 C 0.7798(3) -0.0310(2) -0.35344(19) 0.0486(7) Uani 1 1 d . . . C11 C 0.7060(3) 0.0446(2) -0.30742(19) 0.0467(6) Uani 1 1 d . . . C12 C 0.6456(3) 0.1229(3) -0.3306(2) 0.0542(7) Uani 1 1 d . . . H12 H 0.6491 0.1333 -0.3870 0.065 Uiso 1 1 calc R . . C13 C 0.5815(3) 0.1838(3) -0.2700(2) 0.0543(7) Uani 1 1 d . . . H13 H 0.5426 0.2359 -0.2857 0.065 Uiso 1 1 calc R . . C14 C 0.5734(3) 0.1689(2) -0.18424(19) 0.0457(6) Uani 1 1 d . . . C15 C 0.5144(3) 0.2209(2) -0.10931(19) 0.0446(6) Uani 1 1 d . . . N16 N 0.4452(2) 0.30389(18) -0.08904(15) 0.0457(5) Uani 1 1 d . . . C17 C 0.4176(3) 0.3166(2) -0.00176(18) 0.0431(6) Uani 1 1 d . . . C18 C 0.3546(3) 0.3867(2) 0.06060(19) 0.0445(6) Uani 1 1 d . . . C19 C 0.2904(3) 0.4709(2) 0.0522(2) 0.0505(7) Uani 1 1 d . . . H19 H 0.2834 0.4873 -0.0022 0.061 Uiso 1 1 calc R . . C20 C 0.2386(3) 0.5283(2) 0.1237(2) 0.0532(7) Uani 1 1 d . . . H20 H 0.1978 0.5841 0.1179 0.064 Uiso 1 1 calc R . . C21 C 0.2469(3) 0.5032(2) 0.2056(2) 0.0478(7) Uani 1 1 d . . . C22 C 0.2015(3) 0.5452(2) 0.2903(2) 0.0500(7) Uani 1 1 d . . . C23 C 0.1340(3) 0.6278(3) 0.3234(2) 0.0585(8) Uani 1 1 d . . . H23 H 0.1092 0.6692 0.2875 0.070 Uiso 1 1 calc R . . C24 C 0.1049(3) 0.6468(3) 0.4105(2) 0.0672(9) Uani 1 1 d . . . H24 H 0.0599 0.7015 0.4331 0.081 Uiso 1 1 calc R . . C25 C 0.1414(3) 0.5859(3) 0.4647(2) 0.0697(9) Uani 1 1 d . . . H25 H 0.1199 0.6001 0.5228 0.084 Uiso 1 1 calc R . . C26 C 0.2093(3) 0.5044(3) 0.4344(2) 0.0625(8) Uani 1 1 d . . . H26 H 0.2340 0.4638 0.4710 0.075 Uiso 1 1 calc R . . C27 C 0.2392(3) 0.4855(2) 0.3471(2) 0.0518(7) Uani 1 1 d . . . N28 N 0.3050(2) 0.4097(2) 0.30012(16) 0.0548(6) Uani 1 1 d . . . H28 H 0.3372 0.3636 0.3208 0.066 Uiso 1 1 calc R . . C29 C 0.3105(3) 0.4200(2) 0.21523(19) 0.0465(6) Uani 1 1 d . . . C30 C 0.3649(3) 0.3617(2) 0.14315(19) 0.0448(6) Uani 1 1 d . . . S31 S 0.44614(7) 0.25562(6) 0.14345(5) 0.0495(2) Uani 1 1 d . . . C32 C 0.4700(3) 0.2430(2) 0.03265(18) 0.0446(6) Uani 1 1 d . . . C33 C 0.5292(3) 0.1825(2) -0.03527(19) 0.0460(6) Uani 1 1 d . . . C34 C 0.4114(3) 0.3696(2) -0.1474(2) 0.0490(7) Uani 1 1 d . . . C35 C 0.2787(4) 0.3203(3) -0.2078(3) 0.0805(12) Uani 1 1 d D . . C36 C 0.2565(4) 0.3984(3) -0.2646(3) 0.0880(13) Uani 1 1 d . . . H36A H 0.3322 0.4165 -0.2883 0.106 Uiso 1 1 calc R . . H36B H 0.1881 0.3555 -0.3179 0.106 Uiso 1 1 calc R . . C37 C 0.2250(4) 0.5081(3) -0.2125(3) 0.0787(11) Uani 1 1 d . . . H37A H 0.2939 0.5527 -0.1600 0.094 Uiso 1 1 calc R . . H37B H 0.1495 0.4910 -0.1883 0.094 Uiso 1 1 calc R . . C38 C 0.2029(4) 0.5786(3) -0.2725(3) 0.0850(12) Uani 1 1 d . . . H38A H 0.2806 0.6007 -0.2926 0.102 Uiso 1 1 calc R . . H38B H 0.1389 0.5317 -0.3276 0.102 Uiso 1 1 calc R . . C39 C 0.1610(5) 0.6844(4) -0.2233(4) 0.1210(18) Uani 1 1 d . . . H39A H 0.1490 0.7255 -0.2646 0.182 Uiso 1 1 calc R . . H39B H 0.2246 0.7321 -0.1692 0.182 Uiso 1 1 calc R . . H39C H 0.0828 0.6632 -0.2047 0.182 Uiso 1 1 calc R . . C40 C 0.2400(4) 0.1984(4) -0.2658(3) 0.0586(11) Uiso 0.67 1 d PD . . C40A C 0.1790(8) 0.2615(7) -0.1930(6) 0.056(2) Uiso 0.33 1 d PD . . C41 C 0.0916(4) 0.1543(4) -0.2865(3) 0.0972(14) Uani 1 1 d D . . C1S C 0.4549(5) 0.3120(5) 0.5358(3) 0.1124(16) Uani 1 1 d . . . H1S1 H 0.4857 0.2730 0.5744 0.169 Uiso 1 1 calc R . . H1S2 H 0.3641 0.2939 0.5241 0.169 Uiso 1 1 calc R . . H1S3 H 0.4871 0.3929 0.5669 0.169 Uiso 1 1 calc R . . C2S C 0.4979(3) 0.2754(4) 0.4464(3) 0.0798(11) Uani 1 1 d . . . O3S O 0.4742(3) 0.3096(3) 0.3844(2) 0.1159(11) Uani 1 1 d . . . O4S O 0.5666(2) 0.2001(2) 0.4405(2) 0.0839(8) Uani 1 1 d . . . C5S C 0.6145(4) 0.1620(4) 0.3555(3) 0.0952(13) Uani 1 1 d . . . H5S1 H 0.6636 0.2270 0.3455 0.114 Uiso 1 1 calc R . . H5S2 H 0.5447 0.1226 0.3026 0.114 Uiso 1 1 calc R . . C6S C 0.6950(5) 0.0840(4) 0.3657(5) 0.133(2) Uani 1 1 d . . . H6S1 H 0.7287 0.0582 0.3104 0.200 Uiso 1 1 calc R . . H6S2 H 0.6453 0.0195 0.3747 0.200 Uiso 1 1 calc R . . H6S3 H 0.7633 0.1236 0.4184 0.200 Uiso 1 1 calc R . . C7S C 0.8269(4) -0.0206(4) 0.1031(3) 0.0917(12) Uani 1 1 d . . . H7S1 H 0.8490 -0.0371 0.1585 0.138 Uiso 1 1 calc R . . H7S2 H 0.7364 -0.0369 0.0852 0.138 Uiso 1 1 calc R . . H7S3 H 0.8624 0.0586 0.1150 0.138 Uiso 1 1 calc R . . C8S C 0.8780(3) -0.0925(3) 0.0268(3) 0.0743(11) Uani 1 1 d . . . O9S O 0.8663(3) -0.0923(2) -0.0515(2) 0.0914(8) Uani 1 1 d . . . O10S O 0.9417(2) -0.1590(2) 0.05450(18) 0.0798(7) Uani 1 1 d . . . C11S C 0.9965(4) -0.2312(4) -0.0141(3) 0.0886(12) Uani 1 1 d . . . H11A H 1.0590 -0.1851 -0.0344 0.106 Uiso 1 1 calc R . . H11B H 0.9314 -0.2802 -0.0679 0.106 Uiso 1 1 calc R . . C12S C 1.0581(4) -0.3023(4) 0.0308(4) 0.1022(15) Uani 1 1 d . . . H12A H 1.0962 -0.3512 -0.0132 0.153 Uiso 1 1 calc R . . H12B H 0.9953 -0.3480 0.0501 0.153 Uiso 1 1 calc R . . H12C H 1.1221 -0.2530 0.0840 0.153 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 0.0669(5) 0.0619(5) 0.0480(4) 0.0303(4) 0.0213(3) 0.0352(4) C2 0.0494(16) 0.0524(16) 0.0436(15) 0.0232(13) 0.0130(12) 0.0176(13) C3 0.0492(16) 0.0490(15) 0.0439(15) 0.0199(12) 0.0119(12) 0.0149(13) N4 0.0617(15) 0.0596(14) 0.0490(14) 0.0287(12) 0.0202(12) 0.0289(12) C5 0.0503(16) 0.0515(16) 0.0490(16) 0.0179(13) 0.0145(13) 0.0166(13) C6 0.066(2) 0.0618(19) 0.063(2) 0.0247(16) 0.0215(16) 0.0259(16) C7 0.075(2) 0.072(2) 0.068(2) 0.0203(18) 0.0285(18) 0.0348(18) C8 0.083(2) 0.083(2) 0.060(2) 0.0211(18) 0.0323(18) 0.033(2) C9 0.070(2) 0.071(2) 0.0488(17) 0.0247(15) 0.0207(15) 0.0220(17) C10 0.0502(16) 0.0524(16) 0.0431(15) 0.0156(13) 0.0127(13) 0.0123(13) C11 0.0504(16) 0.0524(16) 0.0414(15) 0.0197(12) 0.0118(13) 0.0146(13) C12 0.0668(19) 0.0635(18) 0.0451(16) 0.0291(14) 0.0178(14) 0.0239(15) C13 0.0671(19) 0.0597(17) 0.0503(17) 0.0308(14) 0.0154(15) 0.0265(15) C14 0.0479(15) 0.0481(15) 0.0457(15) 0.0204(13) 0.0089(13) 0.0166(13) C15 0.0499(16) 0.0457(15) 0.0437(15) 0.0200(12) 0.0089(12) 0.0178(12) N16 0.0534(13) 0.0472(12) 0.0438(13) 0.0213(10) 0.0099(10) 0.0208(11) C17 0.0474(15) 0.0452(14) 0.0401(14) 0.0175(12) 0.0076(12) 0.0160(12) C18 0.0453(15) 0.0436(14) 0.0441(15) 0.0160(12) 0.0041(12) 0.0123(12) C19 0.0595(18) 0.0521(16) 0.0461(16) 0.0211(13) 0.0079(14) 0.0236(14) C20 0.0598(18) 0.0524(16) 0.0529(17) 0.0201(14) 0.0092(14) 0.0263(14) C21 0.0465(16) 0.0465(15) 0.0487(16) 0.0138(13) 0.0060(13) 0.0154(12) C22 0.0483(16) 0.0492(15) 0.0496(16) 0.0129(13) 0.0094(13) 0.0140(13) C23 0.0589(19) 0.0608(18) 0.0577(19) 0.0158(15) 0.0138(15) 0.0271(15) C24 0.066(2) 0.075(2) 0.063(2) 0.0152(17) 0.0200(17) 0.0332(18) C25 0.073(2) 0.081(2) 0.0540(19) 0.0143(17) 0.0235(17) 0.0258(19) C26 0.072(2) 0.066(2) 0.0556(19) 0.0228(16) 0.0198(16) 0.0254(17) C27 0.0543(17) 0.0529(16) 0.0487(16) 0.0152(13) 0.0142(13) 0.0166(14) N28 0.0671(16) 0.0581(14) 0.0507(14) 0.0245(12) 0.0176(12) 0.0295(13) C29 0.0509(16) 0.0477(15) 0.0443(15) 0.0183(12) 0.0092(12) 0.0169(13) C30 0.0471(15) 0.0429(14) 0.0457(15) 0.0156(12) 0.0077(12) 0.0158(12) S31 0.0598(5) 0.0556(4) 0.0457(4) 0.0251(3) 0.0155(3) 0.0280(3) C32 0.0489(15) 0.0483(15) 0.0413(14) 0.0185(12) 0.0099(12) 0.0180(13) C33 0.0510(16) 0.0489(15) 0.0457(15) 0.0214(13) 0.0115(13) 0.0204(13) C34 0.0559(17) 0.0489(15) 0.0497(16) 0.0273(13) 0.0032(13) 0.0182(13) C35 0.095(3) 0.0499(18) 0.081(2) 0.0328(17) -0.038(2) 0.0022(17) C36 0.111(3) 0.063(2) 0.081(3) 0.0399(19) -0.032(2) 0.008(2) C37 0.076(2) 0.070(2) 0.100(3) 0.053(2) -0.003(2) 0.0152(19) C38 0.089(3) 0.074(2) 0.104(3) 0.056(2) -0.003(2) 0.018(2) C39 0.142(4) 0.112(4) 0.156(5) 0.084(4) 0.042(4) 0.071(3) C41 0.068(2) 0.115(3) 0.096(3) 0.058(3) -0.023(2) -0.020(2) C1S 0.092(3) 0.142(4) 0.100(4) 0.044(3) 0.018(3) 0.020(3) C2S 0.061(2) 0.102(3) 0.085(3) 0.049(2) 0.005(2) 0.018(2) O3S 0.116(2) 0.163(3) 0.114(2) 0.089(2) 0.0214(19) 0.072(2) O4S 0.0764(17) 0.0945(18) 0.092(2) 0.0534(16) 0.0057(15) 0.0193(15) C5S 0.086(3) 0.096(3) 0.098(3) 0.034(3) 0.013(3) 0.016(2) C6S 0.111(4) 0.092(3) 0.194(6) 0.042(4) 0.026(4) 0.037(3) C7S 0.106(3) 0.087(3) 0.098(3) 0.052(2) 0.013(3) 0.030(2) C8S 0.070(2) 0.072(2) 0.087(3) 0.053(2) -0.006(2) 0.0039(18) O9S 0.0931(19) 0.107(2) 0.0880(19) 0.0628(17) -0.0024(15) 0.0198(16) O10S 0.0898(18) 0.0809(16) 0.0815(17) 0.0477(14) 0.0051(14) 0.0256(14) C11S 0.082(3) 0.091(3) 0.102(3) 0.053(3) 0.007(2) 0.019(2) C12S 0.090(3) 0.096(3) 0.132(4) 0.061(3) 0.001(3) 0.027(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 C33 1.735(3) . ? S1 C2 1.751(3) . ? C2 C3 1.390(4) . ? C2 C14 1.413(4) . ? C3 N4 1.378(3) . ? C3 C11 1.407(4) . ? N4 C5 1.377(4) . ? N4 H4 0.8600 . ? C5 C6 1.394(4) . ? C5 C10 1.412(4) . ? C6 C7 1.372(5) . ? C6 H6 0.9300 . ? C7 C8 1.383(5) . ? C7 H7 0.9300 . ? C8 C9 1.383(5) . ? C8 H8 0.9300 . ? C9 C10 1.398(4) . ? C9 H9 0.9300 . ? C10 C11 1.444(4) . ? C11 C12 1.406(4) . ? C12 C13 1.371(4) . ? C12 H12 0.9300 . ? C13 C14 1.414(4) . ? C13 H13 0.9300 . ? C14 C15 1.436(4) . ? C15 C33 1.389(4) . ? C15 N16 1.391(3) . ? N16 C17 1.389(3) . ? N16 C34 1.474(3) . ? C17 C32 1.391(4) . ? C17 C18 1.433(4) . ? C18 C30 1.411(4) . ? C18 C19 1.418(4) . ? C19 C20 1.371(4) . ? C19 H19 0.9300 . ? C20 C21 1.402(4) . ? C20 H20 0.9300 . ? C21 C29 1.407(4) . ? C21 C22 1.440(4) . ? C22 C23 1.398(4) . ? C22 C27 1.407(4) . ? C23 C24 1.383(5) . ? C23 H23 0.9300 . ? C24 C25 1.385(5) . ? C24 H24 0.9300 . ? C25 C26 1.383(4) . ? C25 H25 0.9300 . ? C26 C27 1.389(4) . ? C26 H26 0.9300 . ? C27 N28 1.387(4) . ? N28 C29 1.372(4) . ? N28 H28 0.8600 . ? C29 C30 1.399(4) . ? C30 S31 1.751(3) . ? S31 C32 1.731(3) . ? C32 C33 1.401(4) . ? C34 C35 1.524(4) . ? C35 C40A 1.298(8) . ? C35 C40 1.470(5) . ? C35 C36 1.558(4) . ? C36 C37 1.498(6) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.513(4) . ? C37 H37A 0.9700 . ? C37 H37B 0.9700 . ? C38 C39 1.505(6) . ? C38 H38A 0.9700 . ? C38 H38B 0.9700 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? C40 C41 1.575(6) . ? C40A C41 1.663(9) . ? C1S C2S 1.481(6) . ? C1S H1S1 0.9600 . ? C1S H1S2 0.9600 . ? C1S H1S3 0.9600 . ? C2S O3S 1.195(4) . ? C2S O4S 1.314(5) . ? O4S C5S 1.450(5) . ? C5S C6S 1.477(6) . ? C5S H5S1 0.9700 . ? C5S H5S2 0.9700 . ? C6S H6S1 0.9600 . ? C6S H6S2 0.9600 . ? C6S H6S3 0.9600 . ? C7S C8S 1.488(6) . ? C7S H7S1 0.9600 . ? C7S H7S2 0.9600 . ? C7S H7S3 0.9600 . ? C8S O9S 1.205(4) . ? C8S O10S 1.329(4) . ? O10S C11S 1.441(5) . ? C11S C12S 1.508(5) . ? C11S H11A 0.9700 . ? C11S H11B 0.9700 . ? C12S H12A 0.9600 . ? C12S H12B 0.9600 . ? C12S H12C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C33 S1 C2 89.85(13) . . ? C3 C2 C14 119.2(2) . . ? C3 C2 S1 126.1(2) . . ? C14 C2 S1 114.6(2) . . ? N4 C3 C2 129.7(2) . . ? N4 C3 C11 109.2(2) . . ? C2 C3 C11 121.1(2) . . ? C5 N4 C3 108.8(2) . . ? C5 N4 H4 125.6 . . ? C3 N4 H4 125.6 . . ? N4 C5 C6 129.1(3) . . ? N4 C5 C10 109.2(2) . . ? C6 C5 C10 121.8(3) . . ? C7 C6 C5 117.5(3) . . ? C7 C6 H6 121.2 . . ? C5 C6 H6 121.2 . . ? C6 C7 C8 121.8(3) . . ? C6 C7 H7 119.1 . . ? C8 C7 H7 119.1 . . ? C7 C8 C9 121.3(3) . . ? C7 C8 H8 119.3 . . ? C9 C8 H8 119.3 . . ? C8 C9 C10 118.6(3) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C9 C10 C5 119.0(3) . . ? C9 C10 C11 134.8(3) . . ? C5 C10 C11 106.2(2) . . ? C12 C11 C3 119.3(3) . . ? C12 C11 C10 134.1(3) . . ? C3 C11 C10 106.6(2) . . ? C13 C12 C11 119.9(3) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 121.3(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C2 C14 C13 119.1(3) . . ? C2 C14 C15 108.3(2) . . ? C13 C14 C15 132.6(2) . . ? C33 C15 N16 108.7(2) . . ? C33 C15 C14 114.7(2) . . ? N16 C15 C14 136.6(2) . . ? C17 N16 C15 107.2(2) . . ? C17 N16 C34 126.1(2) . . ? C15 N16 C34 126.6(2) . . ? N16 C17 C32 109.0(2) . . ? N16 C17 C18 136.7(2) . . ? C32 C17 C18 114.3(2) . . ? C30 C18 C19 119.7(2) . . ? C30 C18 C17 108.6(2) . . ? C19 C18 C17 131.7(3) . . ? C20 C19 C18 120.4(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 120.4(3) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C20 C21 C29 119.9(3) . . ? C20 C21 C22 133.7(3) . . ? C29 C21 C22 106.4(2) . . ? C23 C22 C27 119.1(3) . . ? C23 C22 C21 134.0(3) . . ? C27 C22 C21 106.9(2) . . ? C24 C23 C22 118.7(3) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C23 C24 C25 121.2(3) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C26 C25 C24 121.5(3) . . ? C26 C25 H25 119.2 . . ? C24 C25 H25 119.2 . . ? C25 C26 C27 117.4(3) . . ? C25 C26 H26 121.3 . . ? C27 C26 H26 121.3 . . ? N28 C27 C26 129.4(3) . . ? N28 C27 C22 108.6(2) . . ? C26 C27 C22 122.0(3) . . ? C29 N28 C27 108.9(2) . . ? C29 N28 H28 125.6 . . ? C27 N28 H28 125.6 . . ? N28 C29 C30 130.4(2) . . ? N28 C29 C21 109.3(2) . . ? C30 C29 C21 120.3(2) . . ? C29 C30 C18 119.2(2) . . ? C29 C30 S31 126.1(2) . . ? C18 C30 S31 114.6(2) . . ? C32 S31 C30 89.64(13) . . ? C17 C32 C33 107.2(2) . . ? C17 C32 S31 112.9(2) . . ? C33 C32 S31 139.9(2) . . ? C15 C33 C32 107.9(2) . . ? C15 C33 S1 112.5(2) . . ? C32 C33 S1 139.7(2) . . ? N16 C34 C35 113.5(2) . . ? C40A C35 C40 64.0(4) . . ? C40A C35 C34 129.3(5) . . ? C40 C35 C34 119.4(3) . . ? C40A C35 C36 117.1(5) . . ? C40 C35 C36 112.4(3) . . ? C34 C35 C36 107.6(3) . . ? C37 C36 C35 115.7(3) . . ? C37 C36 H36A 108.3 . . ? C35 C36 H36A 108.3 . . ? C37 C36 H36B 108.3 . . ? C35 C36 H36B 108.3 . . ? H36A C36 H36B 107.4 . . ? C36 C37 C38 112.8(4) . . ? C36 C37 H37A 109.0 . . ? C38 C37 H37A 109.0 . . ? C36 C37 H37B 109.0 . . ? C38 C37 H37B 109.0 . . ? H37A C37 H37B 107.8 . . ? C39 C38 C37 113.4(4) . . ? C39 C38 H38A 108.9 . . ? C37 C38 H38A 108.9 . . ? C39 C38 H38B 108.9 . . ? C37 C38 H38B 108.9 . . ? H38A C38 H38B 107.7 . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C35 C40 C41 110.6(4) . . ? C35 C40A C41 114.8(6) . . ? C40 C41 C40A 54.1(4) . . ? C2S C1S H1S1 109.5 . . ? C2S C1S H1S2 109.5 . . ? H1S1 C1S H1S2 109.5 . . ? C2S C1S H1S3 109.5 . . ? H1S1 C1S H1S3 109.5 . . ? H1S2 C1S H1S3 109.5 . . ? O3S C2S O4S 121.8(4) . . ? O3S C2S C1S 124.7(4) . . ? O4S C2S C1S 113.5(4) . . ? C2S O4S C5S 116.6(3) . . ? O4S C5S C6S 107.8(4) . . ? O4S C5S H5S1 110.1 . . ? C6S C5S H5S1 110.1 . . ? O4S C5S H5S2 110.1 . . ? C6S C5S H5S2 110.1 . . ? H5S1 C5S H5S2 108.5 . . ? C5S C6S H6S1 109.5 . . ? C5S C6S H6S2 109.5 . . ? H6S1 C6S H6S2 109.5 . . ? C5S C6S H6S3 109.5 . . ? H6S1 C6S H6S3 109.5 . . ? H6S2 C6S H6S3 109.5 . . ? C8S C7S H7S1 109.5 . . ? C8S C7S H7S2 109.5 . . ? H7S1 C7S H7S2 109.5 . . ? C8S C7S H7S3 109.5 . . ? H7S1 C7S H7S3 109.5 . . ? H7S2 C7S H7S3 109.5 . . ? O9S C8S O10S 122.0(4) . . ? O9S C8S C7S 125.8(3) . . ? O10S C8S C7S 112.1(3) . . ? C8S O10S C11S 116.5(3) . . ? O10S C11S C12S 107.4(4) . . ? O10S C11S H11A 110.2 . . ? C12S C11S H11A 110.2 . . ? O10S C11S H11B 110.2 . . ? C12S C11S H11B 110.2 . . ? H11A C11S H11B 108.5 . . ? C11S C12S H12A 109.5 . . ? C11S C12S H12B 109.5 . . ? H12A C12S H12B 109.5 . . ? C11S C12S H12C 109.5 . . ? H12A C12S H12C 109.5 . . ? H12B C12S H12C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C33 S1 C2 C3 178.6(3) . . . . ? C33 S1 C2 C14 -1.7(2) . . . . ? C14 C2 C3 N4 179.1(3) . . . . ? S1 C2 C3 N4 -1.2(5) . . . . ? C14 C2 C3 C11 -0.9(4) . . . . ? S1 C2 C3 C11 178.8(2) . . . . ? C2 C3 N4 C5 179.8(3) . . . . ? C11 C3 N4 C5 -0.2(3) . . . . ? C3 N4 C5 C6 -180.0(3) . . . . ? C3 N4 C5 C10 -0.2(3) . . . . ? N4 C5 C6 C7 -179.9(3) . . . . ? C10 C5 C6 C7 0.4(5) . . . . ? C5 C6 C7 C8 0.1(5) . . . . ? C6 C7 C8 C9 -0.5(6) . . . . ? C7 C8 C9 C10 0.5(5) . . . . ? C8 C9 C10 C5 0.0(5) . . . . ? C8 C9 C10 C11 179.0(3) . . . . ? N4 C5 C10 C9 179.8(3) . . . . ? C6 C5 C10 C9 -0.4(4) . . . . ? N4 C5 C10 C11 0.5(3) . . . . ? C6 C5 C10 C11 -179.7(3) . . . . ? N4 C3 C11 C12 -179.6(3) . . . . ? C2 C3 C11 C12 0.4(4) . . . . ? N4 C3 C11 C10 0.5(3) . . . . ? C2 C3 C11 C10 -179.5(3) . . . . ? C9 C10 C11 C12 0.4(6) . . . . ? C5 C10 C11 C12 179.5(3) . . . . ? C9 C10 C11 C3 -179.8(3) . . . . ? C5 C10 C11 C3 -0.6(3) . . . . ? C3 C11 C12 C13 0.4(4) . . . . ? C10 C11 C12 C13 -179.8(3) . . . . ? C11 C12 C13 C14 -0.7(5) . . . . ? C3 C2 C14 C13 0.6(4) . . . . ? S1 C2 C14 C13 -179.2(2) . . . . ? C3 C2 C14 C15 -178.9(2) . . . . ? S1 C2 C14 C15 1.4(3) . . . . ? C12 C13 C14 C2 0.2(4) . . . . ? C12 C13 C14 C15 179.5(3) . . . . ? C2 C14 C15 C33 -0.2(3) . . . . ? C13 C14 C15 C33 -179.5(3) . . . . ? C2 C14 C15 N16 178.6(3) . . . . ? C13 C14 C15 N16 -0.8(6) . . . . ? C33 C15 N16 C17 0.1(3) . . . . ? C14 C15 N16 C17 -178.7(3) . . . . ? C33 C15 N16 C34 177.9(2) . . . . ? C14 C15 N16 C34 -0.8(5) . . . . ? C15 N16 C17 C32 0.5(3) . . . . ? C34 N16 C17 C32 -177.3(2) . . . . ? C15 N16 C17 C18 178.0(3) . . . . ? C34 N16 C17 C18 0.2(5) . . . . ? N16 C17 C18 C30 -176.6(3) . . . . ? C32 C17 C18 C30 0.8(3) . . . . ? N16 C17 C18 C19 2.5(5) . . . . ? C32 C17 C18 C19 179.9(3) . . . . ? C30 C18 C19 C20 0.1(4) . . . . ? C17 C18 C19 C20 -179.0(3) . . . . ? C18 C19 C20 C21 -0.9(4) . . . . ? C19 C20 C21 C29 1.0(4) . . . . ? C19 C20 C21 C22 -178.5(3) . . . . ? C20 C21 C22 C23 -1.3(6) . . . . ? C29 C21 C22 C23 179.1(3) . . . . ? C20 C21 C22 C27 179.5(3) . . . . ? C29 C21 C22 C27 -0.1(3) . . . . ? C27 C22 C23 C24 -1.0(4) . . . . ? C21 C22 C23 C24 179.8(3) . . . . ? C22 C23 C24 C25 0.1(5) . . . . ? C23 C24 C25 C26 0.5(5) . . . . ? C24 C25 C26 C27 -0.2(5) . . . . ? C25 C26 C27 N28 -179.7(3) . . . . ? C25 C26 C27 C22 -0.8(5) . . . . ? C23 C22 C27 N28 -179.5(3) . . . . ? C21 C22 C27 N28 -0.1(3) . . . . ? C23 C22 C27 C26 1.4(5) . . . . ? C21 C22 C27 C26 -179.3(3) . . . . ? C26 C27 N28 C29 179.4(3) . . . . ? C22 C27 N28 C29 0.3(3) . . . . ? C27 N28 C29 C30 -179.2(3) . . . . ? C27 N28 C29 C21 -0.4(3) . . . . ? C20 C21 C29 N28 -179.3(3) . . . . ? C22 C21 C29 N28 0.3(3) . . . . ? C20 C21 C29 C30 -0.4(4) . . . . ? C22 C21 C29 C30 179.3(3) . . . . ? N28 C29 C30 C18 178.3(3) . . . . ? C21 C29 C30 C18 -0.4(4) . . . . ? N28 C29 C30 S31 -0.8(5) . . . . ? C21 C29 C30 S31 -179.6(2) . . . . ? C19 C18 C30 C29 0.6(4) . . . . ? C17 C18 C30 C29 179.9(2) . . . . ? C19 C18 C30 S31 179.8(2) . . . . ? C17 C18 C30 S31 -0.9(3) . . . . ? C29 C30 S31 C32 179.8(3) . . . . ? C18 C30 S31 C32 0.6(2) . . . . ? N16 C17 C32 C33 -1.0(3) . . . . ? C18 C17 C32 C33 -179.1(2) . . . . ? N16 C17 C32 S31 177.79(18) . . . . ? C18 C17 C32 S31 -0.3(3) . . . . ? C30 S31 C32 C17 -0.2(2) . . . . ? C30 S31 C32 C33 178.0(4) . . . . ? N16 C15 C33 C32 -0.7(3) . . . . ? C14 C15 C33 C32 178.4(2) . . . . ? N16 C15 C33 S1 179.82(18) . . . . ? C14 C15 C33 S1 -1.1(3) . . . . ? C17 C32 C33 C15 1.0(3) . . . . ? S31 C32 C33 C15 -177.2(3) . . . . ? C17 C32 C33 S1 -179.7(3) . . . . ? S31 C32 C33 S1 2.1(6) . . . . ? C2 S1 C33 C15 1.6(2) . . . . ? C2 S1 C33 C32 -177.7(4) . . . . ? C17 N16 C34 C35 -85.6(4) . . . . ? C15 N16 C34 C35 96.9(3) . . . . ? N16 C34 C35 C40A 28.5(7) . . . . ? N16 C34 C35 C40 -50.6(5) . . . . ? N16 C34 C35 C36 179.8(3) . . . . ? C40A C35 C36 C37 77.1(6) . . . . ? C40 C35 C36 C37 148.3(4) . . . . ? C34 C35 C36 C37 -78.2(4) . . . . ? C35 C36 C37 C38 -179.2(3) . . . . ? C36 C37 C38 C39 175.4(4) . . . . ? C40A C35 C40 C41 33.1(5) . . . . ? C34 C35 C40 C41 155.3(3) . . . . ? C36 C35 C40 C41 -77.2(5) . . . . ? C40 C35 C40A C41 -32.2(5) . . . . ? C34 C35 C40A C41 -140.1(5) . . . . ? C36 C35 C40A C41 70.9(7) . . . . ? C35 C40 C41 C40A -28.2(4) . . . . ? C35 C40A C41 C40 33.5(5) . . . . ? O3S C2S O4S C5S 1.2(6) . . . . ? C1S C2S O4S C5S -178.7(4) . . . . ? C2S O4S C5S C6S 176.5(3) . . . . ? O9S C8S O10S C11S 0.1(5) . . . . ? C7S C8S O10S C11S -179.3(3) . . . . ? C8S O10S C11S C12S -177.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.07 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.558 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.044