# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _publ_contact_author_name 'Guo-Xin Jin' _publ_contact_author_address ; ; _publ_contact_author_email gxjin@fudan.edu.cn _publ_author_name 'Guo-Xin Jin' data_f90616d _database_code_depnum_ccdc_archive 'CCDC 805154' #TrackingRef '- 2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H26 N2 S' _chemical_formula_weight 422.57 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 Monoclinic _symmetry_space_group_name_H-M C2/c 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 35.541(8) _cell_length_b 8.540(2) _cell_length_c 16.126(4) _cell_angle_alpha 90.00 _cell_angle_beta 108.397(4) _cell_angle_gamma 90.00 _cell_volume 4644.6(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 924 _cell_measurement_theta_min 2.416 _cell_measurement_theta_max 20.066 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1792 _exptl_absorpt_coefficient_mu 0.157 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9769 _exptl_absorpt_correction_T_max 0.9845 _exptl_absorpt_process_details sadabs _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 '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_% 3.81 _diffrn_reflns_number 9343 _diffrn_reflns_av_R_equivalents 0.0984 _diffrn_reflns_av_sigmaI/netI 0.1394 _diffrn_reflns_limit_h_min -37 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4089 _reflns_number_gt 1573 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0148P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4089 _refine_ls_number_parameters 287 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1565 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0609 _refine_ls_goodness_of_fit_ref 0.752 _refine_ls_restrained_S_all 0.752 _refine_ls_shift/su_max 0.003 _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 0.08837(2) 1.25443(11) 0.49122(6) 0.0711(3) Uani 1 1 d . . . N1 N 0.16820(8) 1.2285(3) 0.6313(2) 0.0628(8) Uani 1 1 d . . . N2 N 0.13183(7) 0.9972(3) 0.69454(17) 0.0567(7) Uani 1 1 d . . . C1 C 0.19468(8) 1.2397(4) 0.7145(2) 0.0495(8) Uani 1 1 d . . . C2 C 0.22404(8) 1.3542(3) 0.7398(2) 0.0564(9) Uani 1 1 d . . . H2 H 0.2256 1.4302 0.6997 0.068 Uiso 1 1 calc R . . C3 C 0.25042(9) 1.3568(4) 0.8217(2) 0.0610(9) Uani 1 1 d . . . H3 H 0.2698 1.4344 0.8362 0.073 Uiso 1 1 calc R . . C4 C 0.24938(8) 1.2483(4) 0.8840(2) 0.0635(9) Uani 1 1 d . . . H4 H 0.2682 1.2486 0.9393 0.076 Uiso 1 1 calc R . . C5 C 0.21928(9) 1.1392(4) 0.8613(2) 0.0599(9) Uani 1 1 d . . . H5 H 0.2174 1.0677 0.9034 0.072 Uiso 1 1 calc R . . C6 C 0.19178(8) 1.1312(3) 0.7789(2) 0.0470(8) Uani 1 1 d . . . C7 C 0.16120(9) 1.0107(3) 0.7627(2) 0.0538(9) Uani 1 1 d . . . H7 H 0.1636 0.9371 0.8066 0.065 Uiso 1 1 calc R . . C8 C 0.16961(10) 1.2936(3) 0.5526(2) 0.0551(9) Uani 1 1 d . . . C9 C 0.20574(9) 1.3349(3) 0.5407(2) 0.0664(10) Uani 1 1 d . . . H9 H 0.2295 1.3182 0.5852 0.080 Uiso 1 1 calc R . . C10 C 0.20582(11) 1.4008(4) 0.4623(3) 0.0748(11) Uani 1 1 d . . . H10 H 0.2298 1.4301 0.4552 0.090 Uiso 1 1 calc R . . C11 C 0.17153(12) 1.4236(4) 0.3953(2) 0.0805(12) Uani 1 1 d . . . H11 H 0.1720 1.4711 0.3438 0.097 Uiso 1 1 calc R . . C12 C 0.13604(11) 1.3751(4) 0.4052(2) 0.0749(11) Uani 1 1 d . . . H12 H 0.1126 1.3860 0.3591 0.090 Uiso 1 1 calc R . . C13 C 0.13516(9) 1.3106(3) 0.4833(2) 0.0560(9) Uani 1 1 d . . . C14 C 0.08705(10) 1.0511(4) 0.4689(2) 0.0610(10) Uani 1 1 d . . . C15 C 0.11712(10) 0.9695(4) 0.4523(2) 0.0760(11) Uani 1 1 d . . . H15 H 0.1402 1.0210 0.4522 0.091 Uiso 1 1 calc R . . C16 C 0.11306(12) 0.8093(5) 0.4358(2) 0.0907(13) Uani 1 1 d . . . H16 H 0.1334 0.7532 0.4249 0.109 Uiso 1 1 calc R . . C17 C 0.07867(14) 0.7343(5) 0.4355(2) 0.0972(13) Uani 1 1 d . . . H17 H 0.0757 0.6275 0.4241 0.117 Uiso 1 1 calc R . . C18 C 0.04927(12) 0.8162(5) 0.4519(3) 0.0987(15) Uani 1 1 d . . . H18 H 0.0262 0.7648 0.4522 0.118 Uiso 1 1 calc R . . C19 C 0.05297(10) 0.9746(5) 0.4682(2) 0.0802(12) Uani 1 1 d . . . H19 H 0.0324 1.0298 0.4788 0.096 Uiso 1 1 calc R . . C20 C 0.10470(9) 0.8717(4) 0.6873(2) 0.0551(9) Uani 1 1 d . . . C21 C 0.11461(9) 0.7196(4) 0.6705(2) 0.0588(9) Uani 1 1 d . . . C22 C 0.08653(11) 0.6039(4) 0.6593(2) 0.0749(11) Uani 1 1 d . . . H22 H 0.0930 0.5020 0.6486 0.090 Uiso 1 1 calc R . . C23 C 0.04943(11) 0.6337(5) 0.6633(2) 0.0795(12) Uani 1 1 d . . . C24 C 0.04033(9) 0.7845(5) 0.6800(2) 0.0772(11) Uani 1 1 d . . . H24 H 0.0152 0.8056 0.6837 0.093 Uiso 1 1 calc R . . C25 C 0.06721(10) 0.9058(4) 0.6915(2) 0.0610(10) Uani 1 1 d . . . C26 C 0.15419(8) 0.6842(3) 0.6592(2) 0.0841(12) Uani 1 1 d . . . H26A H 0.1546 0.5773 0.6410 0.126 Uiso 1 1 calc R . . H26B H 0.1748 0.7003 0.7136 0.126 Uiso 1 1 calc R . . H26C H 0.1584 0.7525 0.6156 0.126 Uiso 1 1 calc R . . C27 C 0.05576(9) 1.0700(4) 0.7059(2) 0.0855(12) Uani 1 1 d . . . H27A H 0.0720 1.1058 0.7623 0.128 Uiso 1 1 calc R . . H27B H 0.0284 1.0724 0.7032 0.128 Uiso 1 1 calc R . . H27C H 0.0596 1.1371 0.6615 0.128 Uiso 1 1 calc R . . C28 C 0.01862(10) 0.5029(4) 0.6473(3) 0.1304(17) Uani 1 1 d . . . H28A H 0.0270 0.4267 0.6933 0.196 Uiso 1 1 calc R . . H28B H 0.0159 0.4536 0.5922 0.196 Uiso 1 1 calc R . . H28C H -0.0064 0.5461 0.6464 0.196 Uiso 1 1 calc R . . H1 H 0.1463(8) 1.175(3) 0.626(2) 0.093(14) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0592(5) 0.0713(6) 0.0776(7) -0.0048(6) 0.0142(5) 0.0001(5) N1 0.0533(18) 0.068(2) 0.061(2) 0.0118(19) 0.0106(18) -0.0149(17) N2 0.0480(16) 0.0573(18) 0.059(2) 0.0061(16) 0.0083(16) -0.0065(15) C1 0.0400(17) 0.050(2) 0.056(2) 0.001(2) 0.0119(18) 0.0072(18) C2 0.0493(19) 0.054(2) 0.065(3) 0.0058(19) 0.017(2) -0.0021(18) C3 0.051(2) 0.066(2) 0.064(3) -0.012(2) 0.014(2) -0.0075(18) C4 0.053(2) 0.082(2) 0.051(2) -0.005(2) 0.0098(18) 0.001(2) C5 0.054(2) 0.067(2) 0.057(3) 0.004(2) 0.016(2) 0.0012(19) C6 0.047(2) 0.045(2) 0.048(2) 0.0032(18) 0.0134(19) 0.0035(17) C7 0.056(2) 0.047(2) 0.060(3) 0.0074(19) 0.021(2) 0.0006(18) C8 0.063(2) 0.046(2) 0.058(3) 0.0032(18) 0.020(2) -0.0052(17) C9 0.063(2) 0.070(2) 0.067(3) -0.001(2) 0.020(2) -0.0103(19) C10 0.088(3) 0.077(3) 0.067(3) -0.004(2) 0.035(3) -0.022(2) C11 0.109(3) 0.076(3) 0.056(3) 0.006(2) 0.027(3) -0.015(3) C12 0.090(3) 0.067(2) 0.060(3) -0.004(2) 0.011(2) -0.003(2) C13 0.059(2) 0.049(2) 0.055(2) -0.0027(18) 0.011(2) -0.0033(17) C14 0.057(2) 0.064(2) 0.056(3) -0.0035(19) 0.010(2) -0.011(2) C15 0.079(3) 0.066(3) 0.085(3) -0.011(2) 0.029(2) -0.010(2) C16 0.093(3) 0.072(3) 0.102(4) -0.016(2) 0.024(3) -0.006(2) C17 0.117(3) 0.064(3) 0.091(3) 0.003(3) 0.005(3) -0.021(3) C18 0.087(3) 0.093(4) 0.100(4) 0.003(3) 0.007(3) -0.036(3) C19 0.062(3) 0.089(3) 0.084(3) -0.008(2) 0.015(2) -0.015(2) C20 0.055(2) 0.054(2) 0.056(3) 0.0038(19) 0.0167(19) -0.008(2) C21 0.054(2) 0.059(2) 0.060(3) 0.008(2) 0.0138(18) 0.002(2) C22 0.084(3) 0.055(2) 0.080(3) -0.004(2) 0.018(2) -0.009(2) C23 0.077(3) 0.076(3) 0.083(3) -0.003(2) 0.021(2) -0.025(3) C24 0.059(2) 0.090(3) 0.087(3) 0.001(2) 0.029(2) -0.010(2) C25 0.057(2) 0.064(3) 0.062(3) 0.000(2) 0.019(2) -0.007(2) C26 0.078(2) 0.073(3) 0.098(3) 0.004(2) 0.022(2) 0.0096(19) C27 0.075(2) 0.083(3) 0.097(3) -0.009(2) 0.025(2) 0.006(2) C28 0.110(3) 0.107(3) 0.169(5) -0.007(3) 0.037(3) -0.057(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C14 1.771(3) . ? S1 C13 1.774(3) . ? N1 C1 1.378(4) . ? N1 C8 1.402(4) . ? N2 C7 1.259(3) . ? N2 C20 1.422(3) . ? C1 C2 1.394(4) . ? C1 C6 1.419(4) . ? C2 C3 1.358(4) . ? C3 C4 1.376(4) . ? C4 C5 1.378(3) . ? C5 C6 1.380(4) . ? C6 C7 1.460(3) . ? C8 C13 1.380(4) . ? C8 C9 1.402(3) . ? C9 C10 1.384(4) . ? C10 C11 1.364(4) . ? C11 C12 1.384(4) . ? C12 C13 1.384(4) . ? C14 C15 1.371(4) . ? C14 C19 1.373(3) . ? C15 C16 1.393(4) . ? C16 C17 1.379(4) . ? C17 C18 1.351(4) . ? C18 C19 1.377(4) . ? C20 C25 1.386(3) . ? C20 C21 1.394(4) . ? C21 C22 1.375(4) . ? C21 C26 1.506(3) . ? C22 C23 1.364(4) . ? C23 C24 1.375(4) . ? C23 C28 1.528(4) . ? C24 C25 1.382(4) . ? C25 C27 1.499(4) . ? 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 C14 S1 C13 102.48(15) . . ? C1 N1 C8 130.3(3) . . ? C7 N2 C20 119.6(3) . . ? N1 C1 C2 123.5(3) . . ? N1 C1 C6 118.9(3) . . ? C2 C1 C6 117.7(3) . . ? C3 C2 C1 121.3(3) . . ? C2 C3 C4 122.0(3) . . ? C3 C4 C5 117.3(3) . . ? C4 C5 C6 122.9(3) . . ? C5 C6 C1 118.7(3) . . ? C5 C6 C7 117.9(3) . . ? C1 C6 C7 123.4(3) . . ? N2 C7 C6 125.9(3) . . ? C13 C8 C9 118.7(3) . . ? C13 C8 N1 119.9(3) . . ? C9 C8 N1 121.3(3) . . ? C10 C9 C8 119.5(3) . . ? C11 C10 C9 121.5(3) . . ? C10 C11 C12 119.0(4) . . ? C13 C12 C11 120.5(4) . . ? C8 C13 C12 120.6(3) . . ? C8 C13 S1 121.7(3) . . ? C12 C13 S1 117.6(3) . . ? C15 C14 C19 119.8(3) . . ? C15 C14 S1 124.4(3) . . ? C19 C14 S1 115.8(3) . . ? C14 C15 C16 119.8(3) . . ? C17 C16 C15 119.6(4) . . ? C18 C17 C16 119.9(4) . . ? C17 C18 C19 120.8(4) . . ? C14 C19 C18 120.0(4) . . ? C25 C20 C21 120.7(3) . . ? C25 C20 N2 118.3(3) . . ? C21 C20 N2 120.8(3) . . ? C22 C21 C20 118.6(3) . . ? C22 C21 C26 120.4(3) . . ? C20 C21 C26 120.9(3) . . ? C23 C22 C21 122.1(3) . . ? C22 C23 C24 118.3(3) . . ? C22 C23 C28 120.5(4) . . ? C24 C23 C28 121.1(4) . . ? C23 C24 C25 122.2(3) . . ? C24 C25 C20 118.1(3) . . ? C24 C25 C27 120.8(3) . . ? C20 C25 C27 121.1(3) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.144 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.034 # Attachment '- 2c.cif' data_f90104a _database_code_depnum_ccdc_archive 'CCDC 805155' #TrackingRef '- 2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H32 N2 S' _chemical_formula_weight 464.65 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.352(6) _cell_length_b 38.303(15) _cell_length_c 10.056(4) _cell_angle_alpha 90.00 _cell_angle_beta 107.106(6) _cell_angle_gamma 90.00 _cell_volume 5284(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 957 _cell_measurement_theta_min 2.371 _cell_measurement_theta_max 24.206 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.168 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1984 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9719 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_process_details sadabs _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 '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_% 7.32 _diffrn_reflns_number 25507 _diffrn_reflns_av_R_equivalents 0.0828 _diffrn_reflns_av_sigmaI/netI 0.1462 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -48 _diffrn_reflns_limit_k_max 44 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 27.01 _reflns_number_total 11211 _reflns_number_gt 3672 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 11211 _refine_ls_number_parameters 629 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1767 _refine_ls_R_factor_gt 0.0524 _refine_ls_wR_factor_ref 0.1310 _refine_ls_wR_factor_gt 0.1046 _refine_ls_goodness_of_fit_ref 0.753 _refine_ls_restrained_S_all 0.753 _refine_ls_shift/su_max 0.003 _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 0.68325(6) 0.11948(2) 0.86693(10) 0.0843(3) Uani 1 1 d . . . N1 N 0.78829(19) 0.17076(7) 0.7373(3) 0.0646(7) Uani 1 1 d . . . N2 N 0.69447(16) 0.14542(5) 0.4762(2) 0.0515(6) Uani 1 1 d . . . C1 C 0.8598(2) 0.18223(7) 0.6799(3) 0.0537(8) Uani 1 1 d . . . C2 C 0.9440(2) 0.19880(7) 0.7590(3) 0.0643(9) Uani 1 1 d . . . H2 H 0.9533 0.2024 0.8534 0.077 Uiso 1 1 calc R . . C3 C 1.0135(2) 0.20984(8) 0.7003(4) 0.0768(10) Uani 1 1 d . . . H3 H 1.0691 0.2209 0.7553 0.092 Uiso 1 1 calc R . . C4 C 1.0023(2) 0.20481(9) 0.5624(4) 0.0852(11) Uani 1 1 d . . . H4 H 1.0492 0.2128 0.5227 0.102 Uiso 1 1 calc R . . C5 C 0.9210(2) 0.18784(8) 0.4832(4) 0.0743(10) Uani 1 1 d . . . H5 H 0.9138 0.1841 0.3894 0.089 Uiso 1 1 calc R . . C6 C 0.84872(19) 0.17609(7) 0.5390(3) 0.0536(8) Uani 1 1 d . . . C7 C 0.7643(2) 0.15968(7) 0.4436(3) 0.0562(8) Uani 1 1 d . . . H7 H 0.7611 0.1596 0.3499 0.067 Uiso 1 1 calc R . . C8 C 0.7657(2) 0.18391(9) 0.8530(3) 0.0602(8) Uani 1 1 d . . . C9 C 0.7166(2) 0.16239(8) 0.9229(3) 0.0612(8) Uani 1 1 d . . . C10 C 0.6882(2) 0.17529(11) 1.0328(4) 0.0835(11) Uani 1 1 d . . . H10 H 0.6542 0.1611 1.0776 0.100 Uiso 1 1 calc R . . C11 C 0.7102(3) 0.20910(13) 1.0763(4) 0.0998(12) Uani 1 1 d . . . H11 H 0.6920 0.2176 1.1516 0.120 Uiso 1 1 calc R . . C12 C 0.7586(3) 0.23024(10) 1.0095(4) 0.0923(12) Uani 1 1 d . . . H12 H 0.7736 0.2530 1.0402 0.111 Uiso 1 1 calc R . . C13 C 0.7851(2) 0.21822(9) 0.8980(4) 0.0752(9) Uani 1 1 d . . . H13 H 0.8163 0.2331 0.8517 0.090 Uiso 1 1 calc R . . C14 C 0.7938(3) 0.09609(10) 0.9257(5) 0.0811(11) Uani 1 1 d . . . C15 C 0.8691(3) 0.10559(11) 1.0326(5) 0.1212(15) Uani 1 1 d . . . H15 H 0.8668 0.1268 1.0765 0.145 Uiso 1 1 calc R . . C16 C 0.9514(3) 0.08449(16) 1.0802(6) 0.156(2) Uani 1 1 d . . . H16 H 1.0031 0.0915 1.1555 0.187 Uiso 1 1 calc R . . C17 C 0.9550(5) 0.05485(17) 1.0181(10) 0.172(3) Uani 1 1 d . . . H17 H 1.0100 0.0408 1.0504 0.206 Uiso 1 1 calc R . . C18 C 0.8823(6) 0.04397(16) 0.9097(8) 0.163(3) Uani 1 1 d . . . H18 H 0.8863 0.0227 0.8670 0.196 Uiso 1 1 calc R . . C19 C 0.8005(4) 0.06511(14) 0.8619(5) 0.1286(17) Uani 1 1 d . . . H19 H 0.7497 0.0581 0.7855 0.154 Uiso 1 1 calc R . . C20 C 0.61406(19) 0.13381(7) 0.3638(3) 0.0491(7) Uani 1 1 d . . . C21 C 0.6141(2) 0.10026(8) 0.3116(3) 0.0563(8) Uani 1 1 d . . . C22 C 0.5337(2) 0.09033(8) 0.2028(3) 0.0696(9) Uani 1 1 d . . . H22 H 0.5321 0.0681 0.1649 0.084 Uiso 1 1 calc R . . C23 C 0.4576(2) 0.11218(10) 0.1509(3) 0.0753(10) Uani 1 1 d . . . H23 H 0.4045 0.1049 0.0781 0.090 Uiso 1 1 calc R . . C24 C 0.4587(2) 0.14505(9) 0.2054(4) 0.0733(10) Uani 1 1 d . . . H24 H 0.4062 0.1599 0.1685 0.088 Uiso 1 1 calc R . . C25 C 0.5358(2) 0.15661(8) 0.3134(3) 0.0596(8) Uani 1 1 d . . . C26 C 0.6980(2) 0.07546(8) 0.3714(4) 0.0737(10) Uani 1 1 d . . . H26 H 0.7459 0.0880 0.4460 0.088 Uiso 1 1 calc R . . C27 C 0.7468(4) 0.06528(16) 0.2701(6) 0.243(4) Uani 1 1 d . . . H27A H 0.7012 0.0539 0.1931 0.365 Uiso 1 1 calc R . . H27B H 0.7993 0.0496 0.3126 0.365 Uiso 1 1 calc R . . H27C H 0.7724 0.0857 0.2375 0.365 Uiso 1 1 calc R . . C28 C 0.6707(4) 0.04469(16) 0.4322(8) 0.275(5) Uani 1 1 d . . . H28A H 0.6153 0.0340 0.3670 0.412 Uiso 1 1 calc R . . H28B H 0.6544 0.0509 0.5151 0.412 Uiso 1 1 calc R . . H28C H 0.7242 0.0285 0.4551 0.412 Uiso 1 1 calc R . . C29 C 0.5367(2) 0.19277(8) 0.3770(4) 0.0860(11) Uani 1 1 d . . . H29 H 0.6055 0.1988 0.4187 0.103 Uiso 1 1 calc R . . C30 C 0.4931(4) 0.19244(10) 0.4910(6) 0.207(3) Uani 1 1 d . . . H30A H 0.5012 0.2149 0.5351 0.311 Uiso 1 1 calc R . . H30B H 0.5246 0.1750 0.5577 0.311 Uiso 1 1 calc R . . H30C H 0.4249 0.1872 0.4553 0.311 Uiso 1 1 calc R . . C31 C 0.4952(3) 0.22060(10) 0.2745(5) 0.1492(19) Uani 1 1 d . . . H31A H 0.4263 0.2170 0.2361 0.224 Uiso 1 1 calc R . . H31B H 0.5256 0.2199 0.2012 0.224 Uiso 1 1 calc R . . H31C H 0.5069 0.2429 0.3197 0.224 Uiso 1 1 calc R . . S2 S 0.23173(6) 0.06185(3) 0.29065(10) 0.0882(3) Uani 1 1 d . . . N3 N 0.22144(19) 0.05982(7) -0.0045(3) 0.0629(8) Uani 1 1 d . . . N4 N 0.19171(15) 0.13015(5) -0.0499(2) 0.0485(6) Uani 1 1 d . . . C32 C 0.1500(2) 0.05538(7) -0.1264(3) 0.0540(8) Uani 1 1 d . . . C33 C 0.1221(2) 0.02213(8) -0.1796(4) 0.0719(9) Uani 1 1 d . . . H33 H 0.1539 0.0025 -0.1331 0.086 Uiso 1 1 calc R . . C34 C 0.0476(3) 0.01843(10) -0.3007(5) 0.0942(12) Uani 1 1 d . . . H34 H 0.0295 -0.0039 -0.3350 0.113 Uiso 1 1 calc R . . C35 C -0.0008(3) 0.04655(11) -0.3728(4) 0.1046(13) Uani 1 1 d . . . H35 H -0.0508 0.0436 -0.4552 0.125 Uiso 1 1 calc R . . C36 C 0.0264(2) 0.07920(9) -0.3203(4) 0.0853(11) Uani 1 1 d . . . H36 H -0.0065 0.0985 -0.3676 0.102 Uiso 1 1 calc R . . C37 C 0.1012(2) 0.08427(7) -0.1992(3) 0.0538(8) Uani 1 1 d . . . C38 C 0.12502(19) 0.12030(7) -0.1558(3) 0.0536(8) Uani 1 1 d . . . H38 H 0.0876 0.1376 -0.2112 0.064 Uiso 1 1 calc R . . C39 C 0.2868(2) 0.03522(7) 0.0765(4) 0.0566(8) Uani 1 1 d . . . C40 C 0.3045(2) 0.03495(7) 0.2191(4) 0.0602(8) Uani 1 1 d . . . C41 C 0.3738(2) 0.01280(8) 0.2999(4) 0.0749(10) Uani 1 1 d . . . H41 H 0.3858 0.0126 0.3959 0.090 Uiso 1 1 calc R . . C42 C 0.4255(3) -0.00905(8) 0.2386(5) 0.0874(11) Uani 1 1 d . . . H42 H 0.4731 -0.0237 0.2934 0.105 Uiso 1 1 calc R . . C43 C 0.4067(3) -0.00918(8) 0.0978(5) 0.0828(11) Uani 1 1 d . . . H43 H 0.4403 -0.0245 0.0565 0.099 Uiso 1 1 calc R . . C44 C 0.3387(2) 0.01300(8) 0.0166(4) 0.0713(9) Uani 1 1 d . . . H44 H 0.3274 0.0131 -0.0793 0.086 Uiso 1 1 calc R . . C45 C 0.3084(2) 0.07044(7) 0.4588(3) 0.0606(8) Uani 1 1 d . . . C46 C 0.3980(2) 0.08621(8) 0.4783(4) 0.0678(9) Uani 1 1 d . . . H46 H 0.4185 0.0918 0.4014 0.081 Uiso 1 1 calc R . . C47 C 0.4567(2) 0.09368(8) 0.6084(4) 0.0727(9) Uani 1 1 d . . . H47 H 0.5175 0.1037 0.6197 0.087 Uiso 1 1 calc R . . C48 C 0.4266(3) 0.08656(8) 0.7221(4) 0.0736(10) Uani 1 1 d . . . H48 H 0.4666 0.0917 0.8108 0.088 Uiso 1 1 calc R . . C49 C 0.3372(3) 0.07174(8) 0.7045(4) 0.0768(10) Uani 1 1 d . . . H49 H 0.3162 0.0673 0.7820 0.092 Uiso 1 1 calc R . . C50 C 0.2777(2) 0.06335(8) 0.5740(4) 0.0704(9) Uani 1 1 d . . . H50 H 0.2173 0.0530 0.5635 0.084 Uiso 1 1 calc R . . C51 C 0.20807(18) 0.16697(6) -0.0302(3) 0.0462(7) Uani 1 1 d . . . C52 C 0.26781(19) 0.18340(7) -0.0987(3) 0.0542(8) Uani 1 1 d . . . C53 C 0.2819(2) 0.21925(7) -0.0804(4) 0.0688(9) Uani 1 1 d . . . H53 H 0.3199 0.2309 -0.1270 0.083 Uiso 1 1 calc R . . C54 C 0.2413(2) 0.23754(8) 0.0040(4) 0.0791(11) Uani 1 1 d . . . H54 H 0.2499 0.2616 0.0126 0.095 Uiso 1 1 calc R . . C55 C 0.1876(2) 0.22055(8) 0.0767(4) 0.0736(10) Uani 1 1 d . . . H55 H 0.1627 0.2332 0.1376 0.088 Uiso 1 1 calc R . . C56 C 0.16950(19) 0.18489(8) 0.0614(3) 0.0564(8) Uani 1 1 d . . . C57 C 0.3175(2) 0.16336(7) -0.1890(3) 0.0584(8) Uani 1 1 d . . . H57 H 0.3229 0.1390 -0.1574 0.070 Uiso 1 1 calc R . . C58 C 0.4207(2) 0.17643(8) -0.1714(4) 0.0916(12) Uani 1 1 d . . . H58A H 0.4183 0.2002 -0.2030 0.137 Uiso 1 1 calc R . . H58B H 0.4510 0.1621 -0.2252 0.137 Uiso 1 1 calc R . . H58C H 0.4578 0.1753 -0.0750 0.137 Uiso 1 1 calc R . . C59 C 0.2584(2) 0.16329(8) -0.3413(3) 0.0823(10) Uani 1 1 d . . . H59A H 0.1955 0.1532 -0.3510 0.123 Uiso 1 1 calc R . . H59B H 0.2918 0.1498 -0.3937 0.123 Uiso 1 1 calc R . . H59C H 0.2505 0.1868 -0.3757 0.123 Uiso 1 1 calc R . . C60 C 0.1162(2) 0.16585(8) 0.1477(4) 0.0748(10) Uani 1 1 d . . . H60 H 0.0898 0.1442 0.0988 0.090 Uiso 1 1 calc R . . C61 C 0.0321(3) 0.18601(12) 0.1730(4) 0.1458(18) Uani 1 1 d . . . H61A H 0.0559 0.2075 0.2196 0.219 Uiso 1 1 calc R . . H61B H 0.0027 0.1723 0.2299 0.219 Uiso 1 1 calc R . . H61C H -0.0155 0.1909 0.0856 0.219 Uiso 1 1 calc R . . C62 C 0.1846(3) 0.15605(10) 0.2863(4) 0.1294(16) Uani 1 1 d . . . H62A H 0.2369 0.1422 0.2728 0.194 Uiso 1 1 calc R . . H62B H 0.1501 0.1428 0.3378 0.194 Uiso 1 1 calc R . . H62C H 0.2108 0.1768 0.3370 0.194 Uiso 1 1 calc R . . H3' H 0.2272(18) 0.0796(7) 0.023(3) 0.063(10) Uiso 1 1 d . . . H1' H 0.7421(19) 0.1552(7) 0.677(3) 0.077(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0741(6) 0.0982(7) 0.0753(7) -0.0010(6) 0.0139(5) -0.0277(5) N1 0.0699(18) 0.0740(18) 0.048(2) -0.0120(15) 0.0153(15) -0.0225(15) N2 0.0521(15) 0.0547(14) 0.0463(17) -0.0012(12) 0.0122(13) -0.0017(12) C1 0.0515(19) 0.0526(17) 0.052(2) 0.0063(16) 0.0070(17) -0.0025(14) C2 0.060(2) 0.069(2) 0.054(2) 0.0002(17) 0.0009(18) -0.0095(16) C3 0.053(2) 0.080(2) 0.084(3) 0.011(2) 0.000(2) -0.0138(17) C4 0.059(2) 0.112(3) 0.084(3) 0.003(3) 0.021(2) -0.020(2) C5 0.059(2) 0.096(2) 0.069(3) -0.008(2) 0.022(2) -0.0114(18) C6 0.0475(18) 0.0592(18) 0.051(2) -0.0016(17) 0.0096(16) -0.0029(14) C7 0.0599(19) 0.0638(19) 0.044(2) -0.0058(16) 0.0142(17) 0.0006(16) C8 0.0569(19) 0.077(2) 0.041(2) -0.0057(19) 0.0054(16) -0.0021(17) C9 0.0555(19) 0.080(2) 0.045(2) -0.0032(19) 0.0092(16) -0.0077(17) C10 0.077(2) 0.110(3) 0.066(3) 0.004(2) 0.024(2) 0.002(2) C11 0.104(3) 0.128(4) 0.070(3) -0.020(3) 0.030(2) 0.012(3) C12 0.112(3) 0.084(3) 0.076(3) -0.016(2) 0.021(3) 0.004(2) C13 0.090(2) 0.071(2) 0.058(3) -0.005(2) 0.011(2) -0.0039(19) C14 0.076(3) 0.067(2) 0.106(4) 0.002(2) 0.037(2) -0.018(2) C15 0.098(3) 0.093(3) 0.153(5) 0.004(3) 0.006(3) 0.003(3) C16 0.093(4) 0.112(4) 0.238(7) 0.039(5) 0.011(4) -0.003(3) C17 0.141(6) 0.093(5) 0.323(12) 0.051(6) 0.132(7) -0.003(4) C18 0.200(8) 0.089(4) 0.251(9) -0.006(5) 0.145(7) -0.006(5) C19 0.147(5) 0.108(4) 0.155(5) -0.003(4) 0.081(4) -0.016(3) C20 0.0455(17) 0.0605(18) 0.038(2) -0.0043(16) 0.0071(15) -0.0053(15) C21 0.063(2) 0.064(2) 0.044(2) -0.0059(17) 0.0188(17) -0.0087(17) C22 0.087(3) 0.072(2) 0.052(2) -0.0131(19) 0.022(2) -0.017(2) C23 0.064(2) 0.100(3) 0.051(2) 0.003(2) 0.0006(18) -0.021(2) C24 0.059(2) 0.090(3) 0.064(3) 0.012(2) 0.0067(19) 0.0015(19) C25 0.0537(19) 0.074(2) 0.046(2) 0.0019(17) 0.0079(16) -0.0032(17) C26 0.080(2) 0.059(2) 0.079(3) -0.0094(19) 0.018(2) 0.0068(18) C27 0.269(7) 0.351(8) 0.136(5) 0.051(5) 0.099(5) 0.232(6) C28 0.147(5) 0.272(7) 0.408(11) 0.268(8) 0.085(6) 0.070(5) C29 0.069(2) 0.073(2) 0.100(3) -0.013(2) 0.000(2) 0.0234(18) C30 0.411(9) 0.106(4) 0.190(6) -0.033(4) 0.222(7) -0.017(4) C31 0.208(5) 0.086(3) 0.164(5) 0.026(3) 0.070(4) 0.037(3) S2 0.0740(6) 0.1127(7) 0.0716(7) -0.0187(6) 0.0116(5) 0.0232(5) N3 0.082(2) 0.0383(16) 0.059(2) -0.0033(16) 0.0075(16) 0.0036(15) N4 0.0524(14) 0.0446(14) 0.0461(17) -0.0004(12) 0.0109(13) 0.0007(11) C32 0.0596(19) 0.0493(19) 0.051(2) -0.0078(17) 0.0124(17) -0.0075(15) C33 0.084(2) 0.055(2) 0.074(3) -0.0128(19) 0.017(2) -0.0077(17) C34 0.096(3) 0.072(3) 0.105(4) -0.034(2) 0.015(3) -0.021(2) C35 0.095(3) 0.094(3) 0.096(4) -0.026(3) -0.018(2) -0.004(2) C36 0.086(3) 0.070(2) 0.080(3) -0.016(2) -0.007(2) -0.0035(19) C37 0.0554(19) 0.0503(18) 0.051(2) -0.0066(16) 0.0091(16) -0.0038(15) C38 0.0547(18) 0.0535(19) 0.050(2) 0.0010(16) 0.0119(16) 0.0064(15) C39 0.069(2) 0.0376(17) 0.062(3) 0.0009(17) 0.0170(19) 0.0033(15) C40 0.068(2) 0.0486(18) 0.061(3) -0.0016(17) 0.0142(18) 0.0044(15) C41 0.096(3) 0.064(2) 0.062(3) 0.0017(19) 0.021(2) 0.0143(19) C42 0.099(3) 0.063(2) 0.092(3) 0.007(2) 0.016(3) 0.018(2) C43 0.101(3) 0.059(2) 0.095(3) -0.003(2) 0.039(3) 0.0214(19) C44 0.094(2) 0.057(2) 0.067(3) 0.0008(19) 0.030(2) 0.0072(18) C45 0.064(2) 0.0624(19) 0.054(2) 0.0007(17) 0.0166(18) 0.0116(16) C46 0.072(2) 0.077(2) 0.058(3) 0.0048(19) 0.026(2) 0.0042(18) C47 0.074(2) 0.077(2) 0.070(3) -0.002(2) 0.025(2) 0.0070(18) C48 0.085(3) 0.072(2) 0.061(3) -0.001(2) 0.018(2) 0.024(2) C49 0.107(3) 0.076(2) 0.061(3) 0.015(2) 0.047(3) 0.015(2) C50 0.074(2) 0.071(2) 0.076(3) 0.000(2) 0.035(2) 0.0038(17) C51 0.0484(16) 0.0389(16) 0.045(2) -0.0029(15) 0.0035(15) 0.0053(13) C52 0.0535(18) 0.0434(17) 0.061(2) 0.0019(16) 0.0089(16) 0.0051(14) C53 0.070(2) 0.0467(19) 0.086(3) -0.0024(18) 0.018(2) -0.0031(15) C54 0.088(3) 0.0435(19) 0.103(3) -0.014(2) 0.023(2) 0.0019(18) C55 0.082(2) 0.063(2) 0.071(3) -0.024(2) 0.014(2) 0.0151(18) C56 0.0570(18) 0.062(2) 0.045(2) -0.0076(17) 0.0064(16) 0.0073(15) C57 0.067(2) 0.0478(17) 0.065(2) 0.0011(17) 0.0277(18) 0.0018(15) C58 0.079(2) 0.093(2) 0.118(4) -0.012(2) 0.052(2) -0.0133(19) C59 0.100(3) 0.083(2) 0.064(3) 0.009(2) 0.025(2) 0.0149(19) C60 0.095(3) 0.078(2) 0.058(3) -0.014(2) 0.034(2) 0.001(2) C61 0.120(3) 0.230(5) 0.110(4) 0.049(3) 0.068(3) 0.053(3) C62 0.154(4) 0.141(4) 0.094(4) 0.049(3) 0.037(3) 0.029(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C9 1.757(3) . ? S1 C14 1.766(4) . ? N1 C1 1.389(3) . ? N1 C8 1.391(3) . ? N2 C7 1.266(3) . ? N2 C20 1.429(3) . ? C1 C2 1.389(4) . ? C1 C6 1.399(4) . ? C2 C3 1.366(4) . ? C3 C4 1.362(4) . ? C4 C5 1.368(4) . ? C5 C6 1.392(4) . ? C6 C7 1.449(4) . ? C8 C13 1.391(4) . ? C8 C9 1.400(4) . ? C9 C10 1.377(4) . ? C10 C11 1.373(4) . ? C11 C12 1.365(4) . ? C12 C13 1.366(4) . ? C14 C15 1.331(5) . ? C14 C19 1.366(5) . ? C15 C16 1.394(5) . ? C16 C17 1.304(7) . ? C17 C18 1.335(8) . ? C18 C19 1.391(7) . ? C20 C21 1.388(3) . ? C20 C25 1.395(3) . ? C21 C22 1.389(4) . ? C21 C26 1.513(4) . ? C22 C23 1.353(4) . ? C23 C24 1.372(4) . ? C24 C25 1.376(4) . ? C25 C29 1.524(4) . ? C26 C28 1.434(5) . ? C26 C27 1.450(5) . ? C29 C30 1.459(5) . ? C29 C31 1.481(5) . ? S2 C45 1.757(3) . ? S2 C40 1.764(3) . ? N3 C32 1.357(3) . ? N3 C39 1.408(4) . ? N4 C38 1.262(3) . ? N4 C51 1.434(3) . ? C32 C33 1.394(4) . ? C32 C37 1.397(4) . ? C33 C34 1.371(4) . ? C34 C35 1.368(4) . ? C35 C36 1.369(4) . ? C36 C37 1.380(4) . ? C37 C38 1.457(3) . ? C39 C40 1.380(4) . ? C39 C44 1.381(4) . ? C40 C41 1.376(4) . ? C41 C42 1.378(4) . ? C42 C43 1.361(4) . ? C43 C44 1.368(4) . ? C45 C46 1.381(4) . ? C45 C50 1.383(4) . ? C46 C47 1.362(4) . ? C47 C48 1.363(4) . ? C48 C49 1.367(4) . ? C49 C50 1.377(4) . ? C51 C56 1.388(3) . ? C51 C52 1.397(3) . ? C52 C53 1.392(3) . ? C52 C57 1.518(4) . ? C53 C54 1.358(4) . ? C54 C55 1.373(4) . ? C55 C56 1.390(4) . ? C56 C60 1.504(4) . ? C57 C59 1.518(4) . ? C57 C58 1.523(3) . ? C60 C62 1.497(4) . ? C60 C61 1.516(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 S1 C14 103.54(17) . . ? C1 N1 C8 128.0(3) . . ? C7 N2 C20 116.5(3) . . ? N1 C1 C2 122.1(3) . . ? N1 C1 C6 119.3(3) . . ? C2 C1 C6 118.5(3) . . ? C3 C2 C1 121.1(3) . . ? C4 C3 C2 120.9(3) . . ? C3 C4 C5 119.0(3) . . ? C4 C5 C6 121.9(3) . . ? C5 C6 C1 118.6(3) . . ? C5 C6 C7 116.8(3) . . ? C1 C6 C7 124.6(3) . . ? N2 C7 C6 126.0(3) . . ? N1 C8 C13 122.7(3) . . ? N1 C8 C9 118.8(3) . . ? C13 C8 C9 118.4(3) . . ? C10 C9 C8 120.2(3) . . ? C10 C9 S1 118.4(3) . . ? C8 C9 S1 121.3(3) . . ? C11 C10 C9 120.0(3) . . ? C12 C11 C10 120.3(4) . . ? C11 C12 C13 120.6(4) . . ? C12 C13 C8 120.5(3) . . ? C15 C14 C19 117.7(4) . . ? C15 C14 S1 124.6(4) . . ? C19 C14 S1 117.6(4) . . ? C14 C15 C16 121.6(5) . . ? C17 C16 C15 119.3(6) . . ? C16 C17 C18 122.1(8) . . ? C17 C18 C19 118.6(7) . . ? C14 C19 C18 120.8(6) . . ? C21 C20 C25 122.1(3) . . ? C21 C20 N2 119.8(3) . . ? C25 C20 N2 118.0(3) . . ? C20 C21 C22 117.3(3) . . ? C20 C21 C26 121.3(3) . . ? C22 C21 C26 121.4(3) . . ? C23 C22 C21 121.6(3) . . ? C22 C23 C24 120.0(3) . . ? C23 C24 C25 121.6(3) . . ? C24 C25 C20 117.4(3) . . ? C24 C25 C29 122.0(3) . . ? C20 C25 C29 120.7(3) . . ? C28 C26 C27 109.1(4) . . ? C28 C26 C21 113.6(3) . . ? C27 C26 C21 112.5(3) . . ? C30 C29 C31 112.1(3) . . ? C30 C29 C25 111.7(3) . . ? C31 C29 C25 114.2(3) . . ? C45 S2 C40 102.91(15) . . ? C32 N3 C39 129.5(3) . . ? C38 N4 C51 117.6(2) . . ? N3 C32 C33 121.1(3) . . ? N3 C32 C37 120.2(3) . . ? C33 C32 C37 118.7(3) . . ? C34 C33 C32 119.8(3) . . ? C35 C34 C33 122.1(3) . . ? C34 C35 C36 118.2(4) . . ? C35 C36 C37 121.9(3) . . ? C36 C37 C32 119.4(3) . . ? C36 C37 C38 116.8(3) . . ? C32 C37 C38 123.8(3) . . ? N4 C38 C37 126.1(3) . . ? C40 C39 C44 119.3(3) . . ? C40 C39 N3 119.6(3) . . ? C44 C39 N3 120.9(3) . . ? C41 C40 C39 119.9(3) . . ? C41 C40 S2 122.1(3) . . ? C39 C40 S2 118.0(2) . . ? C40 C41 C42 120.1(3) . . ? C43 C42 C41 120.0(3) . . ? C42 C43 C44 120.4(3) . . ? C43 C44 C39 120.3(3) . . ? C46 C45 C50 118.7(3) . . ? C46 C45 S2 120.8(3) . . ? C50 C45 S2 120.4(3) . . ? C47 C46 C45 121.0(3) . . ? C46 C47 C48 120.3(3) . . ? C47 C48 C49 119.5(3) . . ? C48 C49 C50 121.0(3) . . ? C49 C50 C45 119.4(3) . . ? C56 C51 C52 121.8(3) . . ? C56 C51 N4 119.8(3) . . ? C52 C51 N4 118.3(2) . . ? C53 C52 C51 117.8(3) . . ? C53 C52 C57 120.1(3) . . ? C51 C52 C57 122.1(2) . . ? C54 C53 C52 121.2(3) . . ? C53 C54 C55 120.0(3) . . ? C54 C55 C56 121.5(3) . . ? C51 C56 C55 117.5(3) . . ? C51 C56 C60 120.9(3) . . ? C55 C56 C60 121.5(3) . . ? C52 C57 C59 112.5(2) . . ? C52 C57 C58 112.1(2) . . ? C59 C57 C58 110.7(3) . . ? C62 C60 C56 110.6(3) . . ? C62 C60 C61 108.0(3) . . ? C56 C60 C61 114.5(3) . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 27.01 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.315 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.033 # Attachment '- 3b.cif' data_a00624a _database_code_depnum_ccdc_archive 'CCDC 805156' #TrackingRef '- 3b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H28 N2 S' _chemical_formula_weight 424.58 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.068(6) _cell_length_b 7.717(3) _cell_length_c 20.796(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.169(6) _cell_angle_gamma 90.00 _cell_volume 2387.3(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 891 _cell_measurement_theta_min 3.065 _cell_measurement_theta_max 22.912 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.153 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_T_max 0.9760 _exptl_absorpt_process_details sadabs _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 '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_% 8.27 _diffrn_reflns_number 11132 _diffrn_reflns_av_R_equivalents 0.0648 _diffrn_reflns_av_sigmaI/netI 0.0638 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.56 _diffrn_reflns_theta_max 26.99 _reflns_number_total 5115 _reflns_number_gt 3058 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0927P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5115 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0914 _refine_ls_R_factor_gt 0.0584 _refine_ls_wR_factor_ref 0.1740 _refine_ls_wR_factor_gt 0.1569 _refine_ls_goodness_of_fit_ref 0.967 _refine_ls_restrained_S_all 0.967 _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 0.42757(4) 0.17621(10) 0.15876(3) 0.0767(3) Uani 1 1 d . . . N1 N 0.62624(12) 0.5439(2) 0.24126(9) 0.0513(5) Uani 1 1 d . . . N2 N 0.44061(12) 0.4539(3) 0.25079(9) 0.0656(6) Uani 1 1 d . . . C1 C 0.53578(14) 0.6475(3) 0.32127(10) 0.0532(5) Uani 1 1 d . . . C2 C 0.56125(16) 0.7172(3) 0.38310(11) 0.0652(6) Uani 1 1 d . . . H2A H 0.6102 0.7920 0.3906 0.078 Uiso 1 1 calc R . . C3 C 0.51549(18) 0.6779(4) 0.43318(11) 0.0718(7) Uani 1 1 d . . . H3 H 0.5334 0.7259 0.4742 0.086 Uiso 1 1 calc R . . C4 C 0.44354(17) 0.5681(3) 0.42269(10) 0.0671(7) Uani 1 1 d . . . H4 H 0.4119 0.5427 0.4565 0.080 Uiso 1 1 calc R . . C5 C 0.41783(15) 0.4952(3) 0.36238(10) 0.0598(6) Uani 1 1 d . . . H5 H 0.3693 0.4192 0.3556 0.072 Uiso 1 1 calc R . . C6 C 0.46372(13) 0.5340(3) 0.31147(9) 0.0533(5) Uani 1 1 d . . . C7 C 0.58450(15) 0.6963(3) 0.26670(10) 0.0598(6) Uani 1 1 d . . . H7A H 0.5427 0.7491 0.2319 0.072 Uiso 1 1 calc R . . H7B H 0.6306 0.7810 0.2821 0.072 Uiso 1 1 calc R . . C8 C 0.69099(14) 0.5857(3) 0.20040(9) 0.0487(5) Uani 1 1 d . . . C9 C 0.66336(15) 0.6013(3) 0.13382(10) 0.0587(6) Uani 1 1 d . . . C10 C 0.72684(18) 0.6390(3) 0.09483(11) 0.0689(7) Uani 1 1 d . . . H10 H 0.7082 0.6497 0.0502 0.083 Uiso 1 1 calc R . . C11 C 0.81639(18) 0.6614(3) 0.11905(11) 0.0650(6) Uani 1 1 d . . . C12 C 0.84222(15) 0.6455(3) 0.18544(11) 0.0599(6) Uani 1 1 d . . . H12 H 0.9026 0.6595 0.2029 0.072 Uiso 1 1 calc R . . C13 C 0.78161(14) 0.6095(3) 0.22694(10) 0.0503(5) Uani 1 1 d . . . C14 C 0.56649(17) 0.5755(4) 0.10381(12) 0.0895(9) Uani 1 1 d . . . H14A H 0.5311 0.6701 0.1158 0.134 Uiso 1 1 calc R . . H14B H 0.5448 0.4688 0.1192 0.134 Uiso 1 1 calc R . . H14C H 0.5618 0.5713 0.0573 0.134 Uiso 1 1 calc R . . C15 C 0.8842(2) 0.7022(5) 0.07494(14) 0.1001(10) Uani 1 1 d . . . H15A H 0.8921 0.8254 0.0730 0.150 Uiso 1 1 calc R . . H15B H 0.8629 0.6585 0.0320 0.150 Uiso 1 1 calc R . . H15C H 0.9406 0.6486 0.0918 0.150 Uiso 1 1 calc R . . C16 C 0.81370(15) 0.5943(3) 0.29917(10) 0.0648(6) Uani 1 1 d . . . H16A H 0.8774 0.6140 0.3081 0.097 Uiso 1 1 calc R . . H16B H 0.8006 0.4804 0.3136 0.097 Uiso 1 1 calc R . . H16C H 0.7836 0.6790 0.3218 0.097 Uiso 1 1 calc R . . C17 C 0.35366(14) 0.4404(3) 0.21617(9) 0.0530(5) Uani 1 1 d . . . C18 C 0.28382(15) 0.5457(3) 0.22857(10) 0.0587(6) Uani 1 1 d . . . H18 H 0.2943 0.6276 0.2617 0.070 Uiso 1 1 calc R . . C19 C 0.19959(16) 0.5310(3) 0.19267(11) 0.0646(6) Uani 1 1 d . . . H19 H 0.1529 0.5997 0.2026 0.078 Uiso 1 1 calc R . . C20 C 0.18413(15) 0.4144(3) 0.14190(12) 0.0660(6) Uani 1 1 d . . . H20 H 0.1276 0.4072 0.1164 0.079 Uiso 1 1 calc R . . C21 C 0.25260(14) 0.3090(3) 0.12921(11) 0.0599(6) Uani 1 1 d . . . H21 H 0.2420 0.2305 0.0949 0.072 Uiso 1 1 calc R . . C22 C 0.33682(14) 0.3175(3) 0.16632(10) 0.0537(5) Uani 1 1 d . . . C23 C 0.38148(14) 0.0317(3) 0.09653(10) 0.0593(6) Uani 1 1 d . . . C24 C 0.3380(2) -0.1133(4) 0.11189(14) 0.0861(8) Uani 1 1 d . . . H24 H 0.3301 -0.1338 0.1547 0.103 Uiso 1 1 calc R . . C25 C 0.3056(2) -0.2297(5) 0.0635(2) 0.1118(11) Uani 1 1 d . . . H25 H 0.2754 -0.3282 0.0739 0.134 Uiso 1 1 calc R . . C26 C 0.3170(3) -0.2031(6) 0.00136(19) 0.1139(12) Uani 1 1 d . . . H26 H 0.2944 -0.2821 -0.0309 0.137 Uiso 1 1 calc R . . C27 C 0.3616(3) -0.0605(6) -0.01360(15) 0.1203(13) Uani 1 1 d . . . H27 H 0.3705 -0.0421 -0.0563 0.144 Uiso 1 1 calc R . . C28 C 0.3941(2) 0.0576(4) 0.03403(13) 0.0892(9) Uani 1 1 d . . . H28 H 0.4247 0.1555 0.0234 0.107 Uiso 1 1 calc R . . H1 H 0.6557(13) 0.485(3) 0.2722(10) 0.048(6) Uiso 1 1 d . . . H2 H 0.4875(15) 0.452(3) 0.2296(10) 0.067(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0570(4) 0.0884(6) 0.0844(5) -0.0291(4) 0.0101(3) 0.0006(3) N1 0.0568(10) 0.0474(11) 0.0505(10) 0.0023(9) 0.0114(8) -0.0019(9) N2 0.0516(10) 0.0943(17) 0.0532(11) -0.0234(10) 0.0153(9) -0.0118(11) C1 0.0577(12) 0.0533(14) 0.0481(12) -0.0052(10) 0.0070(9) 0.0012(10) C2 0.0677(14) 0.0658(16) 0.0591(14) -0.0129(11) 0.0012(11) 0.0013(12) C3 0.0864(17) 0.085(2) 0.0404(12) -0.0083(12) -0.0014(12) 0.0202(15) C4 0.0790(16) 0.0802(18) 0.0438(12) 0.0082(12) 0.0153(11) 0.0262(15) C5 0.0608(12) 0.0657(16) 0.0555(13) 0.0037(11) 0.0172(10) 0.0036(12) C6 0.0547(11) 0.0610(15) 0.0445(11) -0.0049(10) 0.0089(9) 0.0040(11) C7 0.0664(13) 0.0528(14) 0.0621(14) -0.0026(11) 0.0162(11) -0.0050(11) C8 0.0589(12) 0.0415(12) 0.0476(11) -0.0018(9) 0.0148(9) -0.0044(10) C9 0.0720(14) 0.0551(14) 0.0488(12) 0.0016(10) 0.0088(10) -0.0072(12) C10 0.0986(19) 0.0632(17) 0.0466(12) 0.0044(11) 0.0172(12) -0.0112(14) C11 0.0858(17) 0.0521(15) 0.0639(15) 0.0020(11) 0.0327(12) -0.0117(12) C12 0.0623(13) 0.0506(14) 0.0697(15) -0.0032(11) 0.0194(11) -0.0064(11) C13 0.0581(12) 0.0420(12) 0.0516(12) -0.0016(9) 0.0109(9) -0.0034(10) C14 0.0832(18) 0.121(3) 0.0604(15) 0.0062(15) -0.0003(13) -0.0193(18) C15 0.123(2) 0.099(2) 0.092(2) 0.0009(17) 0.0602(18) -0.0253(19) C16 0.0650(13) 0.0699(17) 0.0579(13) -0.0018(11) 0.0051(10) -0.0040(12) C17 0.0559(12) 0.0580(14) 0.0467(11) -0.0004(10) 0.0134(9) -0.0098(11) C18 0.0665(13) 0.0572(14) 0.0532(12) -0.0085(10) 0.0123(10) -0.0031(12) C19 0.0627(13) 0.0605(16) 0.0699(14) 0.0005(12) 0.0084(11) 0.0080(12) C20 0.0595(13) 0.0609(16) 0.0732(15) -0.0028(12) -0.0027(11) -0.0028(12) C21 0.0599(13) 0.0599(15) 0.0591(13) -0.0073(11) 0.0069(10) -0.0107(11) C22 0.0566(12) 0.0546(14) 0.0515(12) -0.0027(10) 0.0136(10) -0.0079(10) C23 0.0602(12) 0.0609(15) 0.0588(13) -0.0034(11) 0.0155(10) 0.0025(11) C24 0.103(2) 0.078(2) 0.0832(18) -0.0030(16) 0.0318(16) -0.0166(17) C25 0.121(3) 0.075(2) 0.141(3) -0.018(2) 0.029(2) -0.027(2) C26 0.134(3) 0.095(3) 0.106(3) -0.046(2) -0.003(2) 0.004(2) C27 0.170(4) 0.128(4) 0.0601(18) -0.016(2) 0.010(2) -0.009(3) C28 0.121(2) 0.082(2) 0.0661(16) 0.0049(15) 0.0198(15) -0.0127(18) _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 C23 1.764(2) . ? S1 C22 1.775(2) . ? N1 C8 1.429(3) . ? N1 C7 1.471(3) . ? N2 C17 1.395(3) . ? N2 C6 1.398(3) . ? C1 C6 1.384(3) . ? C1 C2 1.390(3) . ? C1 C7 1.495(3) . ? C2 C3 1.372(3) . ? C3 C4 1.366(4) . ? C4 C5 1.373(3) . ? C5 C6 1.386(3) . ? C8 C9 1.386(3) . ? C8 C13 1.401(3) . ? C9 C10 1.380(3) . ? C9 C14 1.506(3) . ? C10 C11 1.374(3) . ? C11 C12 1.379(3) . ? C11 C15 1.511(3) . ? C12 C13 1.381(3) . ? C13 C16 1.507(3) . ? C17 C18 1.386(3) . ? C17 C22 1.398(3) . ? C18 C19 1.371(3) . ? C19 C20 1.379(3) . ? C20 C21 1.372(3) . ? C21 C22 1.378(3) . ? C23 C28 1.358(3) . ? C23 C24 1.361(4) . ? C24 C25 1.379(4) . ? C25 C26 1.345(5) . ? C26 C27 1.352(5) . ? C27 C28 1.377(4) . ? 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 C23 S1 C22 103.56(10) . . ? C8 N1 C7 113.90(17) . . ? C17 N2 C6 125.26(19) . . ? C6 C1 C2 118.4(2) . . ? C6 C1 C7 121.08(18) . . ? C2 C1 C7 120.5(2) . . ? C3 C2 C1 121.2(2) . . ? C4 C3 C2 119.9(2) . . ? C3 C4 C5 120.1(2) . . ? C4 C5 C6 120.4(2) . . ? C1 C6 C5 119.95(19) . . ? C1 C6 N2 119.27(19) . . ? C5 C6 N2 120.7(2) . . ? N1 C7 C1 111.18(19) . . ? C9 C8 C13 120.06(18) . . ? C9 C8 N1 119.26(18) . . ? C13 C8 N1 120.68(18) . . ? C10 C9 C8 118.6(2) . . ? C10 C9 C14 120.1(2) . . ? C8 C9 C14 121.3(2) . . ? C11 C10 C9 122.9(2) . . ? C10 C11 C12 117.4(2) . . ? C10 C11 C15 121.6(2) . . ? C12 C11 C15 121.1(2) . . ? C11 C12 C13 122.3(2) . . ? C12 C13 C8 118.69(19) . . ? C12 C13 C16 120.0(2) . . ? C8 C13 C16 121.34(18) . . ? C18 C17 N2 122.6(2) . . ? C18 C17 C22 118.83(19) . . ? N2 C17 C22 118.6(2) . . ? C19 C18 C17 121.0(2) . . ? C18 C19 C20 120.0(2) . . ? C21 C20 C19 119.6(2) . . ? C20 C21 C22 121.2(2) . . ? C21 C22 C17 119.3(2) . . ? C21 C22 S1 125.09(18) . . ? C17 C22 S1 115.53(16) . . ? C28 C23 C24 119.5(2) . . ? C28 C23 S1 120.7(2) . . ? C24 C23 S1 119.72(19) . . ? C23 C24 C25 119.5(3) . . ? C26 C25 C24 121.2(3) . . ? C25 C26 C27 119.3(3) . . ? C26 C27 C28 120.4(3) . . ? C23 C28 C27 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.558 _refine_diff_density_min -0.337 _refine_diff_density_rms 0.046 # Attachment '- 3c.HCl.cif' data_a00610b _database_code_depnum_ccdc_archive 'CCDC 805157' #TrackingRef '- 3c.HCl.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C31 H35 Cl N2 S' _chemical_formula_weight 503.12 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' 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' Cl Cl 0.1484 0.1585 '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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.802(5) _cell_length_b 10.335(5) _cell_length_c 23.884(11) _cell_angle_alpha 90.00 _cell_angle_beta 103.704(7) _cell_angle_gamma 90.00 _cell_volume 2830(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 749 _cell_measurement_theta_min 2.653 _cell_measurement_theta_max 24.284 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.181 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.230 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9641 _exptl_absorpt_correction_T_max 0.9818 _exptl_absorpt_process_details sadabs _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 '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_% 6.87 _diffrn_reflns_number 12465 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.1029 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 26.01 _reflns_number_total 5508 _reflns_number_gt 2351 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0752P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5508 _refine_ls_number_parameters 332 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1496 _refine_ls_R_factor_gt 0.0640 _refine_ls_wR_factor_ref 0.1650 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 0.872 _refine_ls_restrained_S_all 0.872 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.50401(8) 0.69039(9) 0.01153(4) 0.0642(3) Uani 1 1 d . . . N1 N 0.2284(3) 0.7442(3) -0.03635(14) 0.0637(9) Uani 1 1 d . . . H1 H 0.301(3) 0.724(3) -0.0204(13) 0.045(10) Uiso 1 1 d . . . N2 N 0.3623(3) 0.4816(3) 0.05702(12) 0.0483(8) Uani 1 1 d . . . H2A H 0.400(3) 0.566(4) 0.0522(15) 0.076(12) Uiso 1 1 d . . . H2B H 0.403(3) 0.416(3) 0.0441(14) 0.056(11) Uiso 1 1 d . . . S1 S 0.02370(9) 0.74809(12) -0.14313(5) 0.0777(4) Uani 1 1 d . . . C1 C 0.1034(4) 0.6354(4) -0.17422(16) 0.0644(10) Uani 1 1 d . . . C2 C 0.2181(4) 0.6499(4) -0.17644(18) 0.0830(13) Uani 1 1 d . . . H2 H 0.2595 0.7226 -0.1601 0.100 Uiso 1 1 calc R . . C3 C 0.2721(5) 0.5577(6) -0.2026(2) 0.1111(18) Uani 1 1 d . . . H3 H 0.3498 0.5682 -0.2037 0.133 Uiso 1 1 calc R . . C4 C 0.2119(7) 0.4508(6) -0.2269(3) 0.122(2) Uani 1 1 d . . . H4 H 0.2486 0.3886 -0.2445 0.146 Uiso 1 1 calc R . . C5 C 0.0976(7) 0.4354(6) -0.2253(2) 0.117(2) Uani 1 1 d . . . H5 H 0.0566 0.3626 -0.2419 0.140 Uiso 1 1 calc R . . C6 C 0.0429(5) 0.5273(5) -0.1992(2) 0.0912(15) Uani 1 1 d . . . H6 H -0.0349 0.5166 -0.1983 0.109 Uiso 1 1 calc R . . C7 C 0.1257(3) 0.8730(4) -0.11847(16) 0.0595(10) Uani 1 1 d . . . C8 C 0.2133(3) 0.8604(4) -0.06850(15) 0.0537(9) Uani 1 1 d . . . C9 C 0.2930(4) 0.9598(4) -0.05269(18) 0.0688(11) Uani 1 1 d . . . H9 H 0.3533 0.9511 -0.0199 0.083 Uiso 1 1 calc R . . C10 C 0.2842(4) 1.0723(5) -0.0851(2) 0.0801(13) Uani 1 1 d . . . H10 H 0.3381 1.1386 -0.0740 0.096 Uiso 1 1 calc R . . C11 C 0.1960(5) 1.0852(5) -0.1333(2) 0.0860(14) Uani 1 1 d . . . H11 H 0.1894 1.1609 -0.1549 0.103 Uiso 1 1 calc R . . C12 C 0.1170(4) 0.9872(4) -0.15022(18) 0.0731(12) Uani 1 1 d . . . H12 H 0.0572 0.9971 -0.1832 0.088 Uiso 1 1 calc R . . C13 C 0.1551(3) 0.7132(4) 0.00081(14) 0.0516(9) Uani 1 1 d . . . C14 C 0.1644(3) 0.5921(4) 0.02756(14) 0.0519(9) Uani 1 1 d . . . C15 C 0.0901(3) 0.5629(4) 0.06340(16) 0.0695(12) Uani 1 1 d . . . H15 H 0.0946 0.4822 0.0810 0.083 Uiso 1 1 calc R . . C16 C 0.0100(3) 0.6527(5) 0.07301(17) 0.0783(13) Uani 1 1 d . . . H16 H -0.0382 0.6326 0.0974 0.094 Uiso 1 1 calc R . . C17 C 0.0016(3) 0.7702(5) 0.04692(16) 0.0735(12) Uani 1 1 d . . . H17 H -0.0526 0.8304 0.0533 0.088 Uiso 1 1 calc R . . C18 C 0.0734(3) 0.8000(4) 0.01093(16) 0.0641(10) Uani 1 1 d . . . H18 H 0.0667 0.8805 -0.0070 0.077 Uiso 1 1 calc R . . C19 C 0.2442(3) 0.4887(3) 0.01465(15) 0.0560(10) Uani 1 1 d . . . H19A H 0.2564 0.5038 -0.0236 0.067 Uiso 1 1 calc R . . H19B H 0.2058 0.4056 0.0141 0.067 Uiso 1 1 calc R . . C20 C 0.3586(3) 0.4531(4) 0.11746(14) 0.0490(9) Uani 1 1 d . . . C21 C 0.3448(3) 0.3254(4) 0.13228(15) 0.0531(9) Uani 1 1 d . . . C22 C 0.3408(3) 0.3023(4) 0.18964(18) 0.0743(12) Uani 1 1 d . . . H22 H 0.3312 0.2182 0.2016 0.089 Uiso 1 1 calc R . . C23 C 0.3510(4) 0.4022(5) 0.22845(17) 0.0788(13) Uani 1 1 d . . . H23 H 0.3488 0.3850 0.2664 0.095 Uiso 1 1 calc R . . C24 C 0.3644(3) 0.5258(4) 0.21202(17) 0.0696(11) Uani 1 1 d . . . H24 H 0.3709 0.5918 0.2391 0.084 Uiso 1 1 calc R . . C25 C 0.3686(3) 0.5569(4) 0.15599(15) 0.0532(9) Uani 1 1 d . . . C26 C 0.3376(3) 0.2101(4) 0.09230(16) 0.0596(10) Uani 1 1 d . . . H26 H 0.3368 0.2435 0.0538 0.072 Uiso 1 1 calc R . . C27 C 0.2262(3) 0.1329(4) 0.08769(19) 0.0836(13) Uani 1 1 d . . . H27A H 0.2253 0.0972 0.1247 0.125 Uiso 1 1 calc R . . H27B H 0.2230 0.0640 0.0604 0.125 Uiso 1 1 calc R . . H27C H 0.1600 0.1886 0.0751 0.125 Uiso 1 1 calc R . . C28 C 0.4452(3) 0.1233(4) 0.11087(19) 0.0830(13) Uani 1 1 d . . . H28A H 0.5142 0.1732 0.1118 0.124 Uiso 1 1 calc R . . H28B H 0.4404 0.0535 0.0839 0.124 Uiso 1 1 calc R . . H28C H 0.4483 0.0889 0.1485 0.124 Uiso 1 1 calc R . . C29 C 0.3885(3) 0.6972(4) 0.14111(16) 0.0602(10) Uani 1 1 d . . . H29 H 0.3720 0.7048 0.0991 0.072 Uiso 1 1 calc R . . C30 C 0.5145(3) 0.7354(4) 0.16552(18) 0.0782(12) Uani 1 1 d . . . H30A H 0.5340 0.7229 0.2065 0.117 Uiso 1 1 calc R . . H30B H 0.5250 0.8248 0.1570 0.117 Uiso 1 1 calc R . . H30C H 0.5644 0.6828 0.1485 0.117 Uiso 1 1 calc R . . C31 C 0.3069(4) 0.7882(4) 0.16273(19) 0.0914(14) Uani 1 1 d . . . H31A H 0.2277 0.7606 0.1482 0.137 Uiso 1 1 calc R . . H31B H 0.3160 0.8744 0.1496 0.137 Uiso 1 1 calc R . . H31C H 0.3253 0.7870 0.2041 0.137 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 Cl1 0.0624(6) 0.0692(7) 0.0709(6) -0.0029(5) 0.0357(5) -0.0040(5) N1 0.050(2) 0.083(3) 0.065(2) 0.0206(18) 0.0257(17) 0.0135(18) N2 0.052(2) 0.052(2) 0.0466(19) 0.0015(15) 0.0234(16) 0.0016(16) S1 0.0602(7) 0.0955(9) 0.0790(8) -0.0017(6) 0.0198(6) -0.0073(6) C1 0.065(3) 0.073(3) 0.051(2) 0.009(2) 0.005(2) -0.007(2) C2 0.095(4) 0.083(3) 0.075(3) -0.012(2) 0.028(3) 0.000(3) C3 0.123(5) 0.110(5) 0.109(4) -0.026(4) 0.044(4) 0.010(4) C4 0.164(6) 0.101(5) 0.096(4) -0.020(3) 0.022(5) 0.033(5) C5 0.168(7) 0.085(4) 0.084(4) -0.012(3) 0.001(4) -0.005(4) C6 0.107(4) 0.086(4) 0.073(3) 0.012(3) 0.006(3) -0.016(3) C7 0.061(3) 0.068(3) 0.053(2) 0.003(2) 0.021(2) 0.006(2) C8 0.054(2) 0.062(3) 0.053(2) 0.003(2) 0.0276(19) 0.003(2) C9 0.063(3) 0.085(3) 0.063(3) -0.011(2) 0.024(2) 0.000(2) C10 0.089(4) 0.069(3) 0.094(4) -0.014(3) 0.045(3) -0.017(3) C11 0.109(4) 0.070(3) 0.093(4) 0.017(3) 0.052(3) 0.006(3) C12 0.077(3) 0.079(3) 0.066(3) 0.011(2) 0.021(2) 0.010(3) C13 0.043(2) 0.067(3) 0.048(2) 0.0044(18) 0.0162(17) 0.0019(18) C14 0.040(2) 0.070(3) 0.046(2) 0.0015(19) 0.0114(17) -0.0035(18) C15 0.057(3) 0.091(3) 0.064(3) 0.018(2) 0.021(2) -0.005(2) C16 0.054(3) 0.122(4) 0.066(3) 0.015(3) 0.029(2) -0.001(3) C17 0.052(2) 0.114(4) 0.059(3) 0.005(3) 0.023(2) 0.014(2) C18 0.058(2) 0.076(3) 0.062(3) 0.009(2) 0.021(2) 0.010(2) C19 0.053(2) 0.069(3) 0.044(2) 0.0011(18) 0.0080(19) -0.0027(19) C20 0.044(2) 0.065(3) 0.041(2) 0.0058(19) 0.0159(16) 0.0015(17) C21 0.052(2) 0.063(3) 0.047(2) 0.0067(19) 0.0186(17) -0.0075(18) C22 0.085(3) 0.080(3) 0.062(3) 0.018(2) 0.025(2) -0.014(2) C23 0.097(3) 0.101(4) 0.045(2) 0.006(3) 0.031(2) -0.016(3) C24 0.082(3) 0.080(3) 0.050(3) -0.002(2) 0.022(2) -0.007(2) C25 0.049(2) 0.068(3) 0.045(2) 0.003(2) 0.0143(18) 0.0002(18) C26 0.062(2) 0.060(3) 0.062(2) 0.0104(19) 0.0238(19) 0.001(2) C27 0.077(3) 0.082(3) 0.095(3) -0.007(3) 0.026(2) -0.017(2) C28 0.083(3) 0.083(3) 0.088(3) 0.007(3) 0.031(2) 0.014(3) C29 0.069(3) 0.066(3) 0.048(2) -0.0071(19) 0.0193(19) 0.007(2) C30 0.077(3) 0.082(3) 0.078(3) -0.005(2) 0.022(2) -0.017(2) C31 0.103(4) 0.083(3) 0.096(3) -0.012(3) 0.039(3) 0.013(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C8 1.413(4) . ? N1 C13 1.415(4) . ? N2 C20 1.484(4) . ? N2 C19 1.517(4) . ? S1 C1 1.767(4) . ? S1 C7 1.769(4) . ? C1 C2 1.376(5) . ? C1 C6 1.382(6) . ? C2 C3 1.375(6) . ? C3 C4 1.367(7) . ? C4 C5 1.369(8) . ? C5 C6 1.378(7) . ? C7 C8 1.387(5) . ? C7 C12 1.393(5) . ? C8 C9 1.384(5) . ? C9 C10 1.387(6) . ? C10 C11 1.363(6) . ? C11 C12 1.370(6) . ? C13 C18 1.380(5) . ? C13 C14 1.397(5) . ? C14 C15 1.395(5) . ? C14 C19 1.504(5) . ? C15 C16 1.382(5) . ? C16 C17 1.358(6) . ? C17 C18 1.377(5) . ? C20 C21 1.386(5) . ? C20 C25 1.400(5) . ? C21 C22 1.403(5) . ? C21 C26 1.517(5) . ? C22 C23 1.374(5) . ? C23 C24 1.357(5) . ? C24 C25 1.388(5) . ? C25 C29 1.524(5) . ? C26 C27 1.519(5) . ? C26 C28 1.532(5) . ? C29 C30 1.516(5) . ? C29 C31 1.521(5) . ? 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 N1 C13 121.1(3) . . ? C20 N2 C19 115.1(3) . . ? C1 S1 C7 103.48(19) . . ? C2 C1 C6 118.9(4) . . ? C2 C1 S1 124.8(3) . . ? C6 C1 S1 116.2(4) . . ? C3 C2 C1 120.6(5) . . ? C4 C3 C2 120.2(6) . . ? C3 C4 C5 120.0(6) . . ? C4 C5 C6 120.2(6) . . ? C5 C6 C1 120.2(5) . . ? C8 C7 C12 119.5(4) . . ? C8 C7 S1 121.8(3) . . ? C12 C7 S1 118.7(3) . . ? C9 C8 C7 119.0(4) . . ? C9 C8 N1 119.5(4) . . ? C7 C8 N1 121.3(4) . . ? C8 C9 C10 120.9(4) . . ? C11 C10 C9 119.7(4) . . ? C10 C11 C12 120.4(4) . . ? C11 C12 C7 120.5(4) . . ? C18 C13 C14 119.0(3) . . ? C18 C13 N1 121.2(3) . . ? C14 C13 N1 119.8(3) . . ? C15 C14 C13 118.8(3) . . ? C15 C14 C19 119.2(3) . . ? C13 C14 C19 121.8(3) . . ? C16 C15 C14 120.7(4) . . ? C17 C16 C15 120.2(4) . . ? C16 C17 C18 119.8(4) . . ? C17 C18 C13 121.5(4) . . ? C14 C19 N2 114.8(3) . . ? C21 C20 C25 124.0(3) . . ? C21 C20 N2 118.0(3) . . ? C25 C20 N2 118.1(3) . . ? C20 C21 C22 116.4(4) . . ? C20 C21 C26 125.5(3) . . ? C22 C21 C26 118.1(3) . . ? C23 C22 C21 120.9(4) . . ? C24 C23 C22 120.7(4) . . ? C23 C24 C25 122.0(4) . . ? C24 C25 C20 116.1(3) . . ? C24 C25 C29 119.1(3) . . ? C20 C25 C29 124.7(3) . . ? C21 C26 C27 112.2(3) . . ? C21 C26 C28 111.0(3) . . ? C27 C26 C28 110.9(3) . . ? C30 C29 C31 110.5(3) . . ? C30 C29 C25 110.5(3) . . ? C31 C29 C25 111.4(3) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.01 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.467 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.066