# 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_name 'Wu, Ming-Jung' _publ_author_name 'Ming-Jung Wu' _publ_contact_author_email mijuwu@faculty.nsysu.edu.tw data_9252 _database_code_depnum_ccdc_archive 'CCDC 883588' #TrackingRef '- compound_2p.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H16 N2 S' _chemical_formula_sum 'C20 H16 N2 S' _chemical_formula_weight 316.41 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 'C 2/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 26.0310(9) _cell_length_b 5.2668(2) _cell_length_c 25.4350(11) _cell_angle_alpha 90.00 _cell_angle_beta 114.261(2) _cell_angle_gamma 90.00 _cell_volume 3179.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8990 _cell_measurement_theta_min 2.037 _cell_measurement_theta_max 25.028 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.204 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9313 _exptl_absorpt_correction_T_max 1.057 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9281 _diffrn_reflns_av_R_equivalents 0.1016 _diffrn_reflns_av_sigmaI/netI 0.1046 _diffrn_reflns_limit_h_min -30 _diffrn_reflns_limit_h_max 30 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2792 _reflns_number_gt 1648 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0510P)^2^+3.8222P] 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 2792 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1318 _refine_ls_R_factor_gt 0.0664 _refine_ls_wR_factor_ref 0.1602 _refine_ls_wR_factor_gt 0.1323 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 0.34126(4) -0.0336(2) 0.25612(4) 0.0393(3) Uani 1 1 d . . . N1 N 0.24880(13) 0.5197(6) 0.03905(13) 0.0334(8) Uani 1 1 d . . . N2 N 0.29622(14) 0.6605(6) 0.05905(13) 0.0340(8) Uani 1 1 d . . . H2 H 0.3024 0.7914 0.0409 0.041 Uiso 1 1 calc R . . C1 C 0.30494(18) -0.3013(8) 0.26739(18) 0.0500(12) Uani 1 1 d . . . H1A H 0.2679 -0.3167 0.2350 0.075 Uiso 1 1 calc R . . H1B H 0.3000 -0.2785 0.3033 0.075 Uiso 1 1 calc R . . H1C H 0.3269 -0.4556 0.2700 0.075 Uiso 1 1 calc R . . C2 C 0.40572(16) -0.0327(7) 0.31711(15) 0.0301(9) Uani 1 1 d . . . C3 C 0.41865(18) -0.1931(8) 0.36400(17) 0.0385(11) Uani 1 1 d . . . H3 H 0.3920 -0.3162 0.3639 0.046 Uiso 1 1 calc R . . C4 C 0.47009(18) -0.1754(8) 0.41088(17) 0.0422(11) Uani 1 1 d . . . H4 H 0.4783 -0.2857 0.4429 0.051 Uiso 1 1 calc R . . C5 C 0.50960(17) 0.0007(8) 0.41167(17) 0.0434(11) Uani 1 1 d . . . H5 H 0.5449 0.0106 0.4440 0.052 Uiso 1 1 calc R . . C6 C 0.49795(17) 0.1616(8) 0.36573(17) 0.0383(10) Uani 1 1 d . . . H6 H 0.5252 0.2838 0.3668 0.046 Uiso 1 1 calc R . . C7 C 0.44605(16) 0.1480(7) 0.31700(16) 0.0323(10) Uani 1 1 d . . . C8 C 0.43524(16) 0.3167(8) 0.26934(17) 0.0344(10) Uani 1 1 d . . . C9 C 0.42888(15) 0.4622(8) 0.23127(16) 0.0334(10) Uani 1 1 d . . . C10 C 0.42797(17) 0.6487(8) 0.19033(16) 0.0387(11) Uani 1 1 d . . . H10 H 0.4608 0.7509 0.2011 0.046 Uiso 1 1 calc R . . C11 C 0.38652(17) 0.6980(8) 0.13847(16) 0.0360(10) Uani 1 1 d . . . H11 H 0.3935 0.8328 0.1175 0.043 Uiso 1 1 calc R . . C12 C 0.33281(16) 0.5732(8) 0.11053(15) 0.0311(10) Uani 1 1 d . . . C13 C 0.30771(16) 0.3651(7) 0.12442(16) 0.0325(10) Uani 1 1 d . . . H13 H 0.3233 0.2625 0.1580 0.039 Uiso 1 1 calc R . . C14 C 0.25507(16) 0.3387(7) 0.07882(15) 0.0292(9) Uani 1 1 d . . . C15 C 0.20886(16) 0.1584(7) 0.06985(16) 0.0309(9) Uani 1 1 d . . . C16 C 0.21564(17) -0.0351(7) 0.10950(16) 0.0347(10) Uani 1 1 d . . . H16 H 0.2506 -0.0525 0.1421 0.042 Uiso 1 1 calc R . . C17 C 0.17203(18) -0.2027(8) 0.10199(17) 0.0393(11) Uani 1 1 d . . . H17 H 0.1770 -0.3321 0.1297 0.047 Uiso 1 1 calc R . . C18 C 0.12122(18) -0.1815(8) 0.05417(17) 0.0421(11) Uani 1 1 d . . . H18 H 0.0913 -0.2958 0.0491 0.051 Uiso 1 1 calc R . . C19 C 0.11429(18) 0.0052(8) 0.01424(18) 0.0431(11) Uani 1 1 d . . . H19 H 0.0797 0.0179 -0.0189 0.052 Uiso 1 1 calc R . . C20 C 0.15738(18) 0.1758(8) 0.02172(17) 0.0408(11) Uani 1 1 d . . . H20 H 0.1519 0.3053 -0.0061 0.049 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 0.0296(6) 0.0437(7) 0.0382(6) 0.0101(5) 0.0075(5) -0.0021(5) N1 0.035(2) 0.032(2) 0.0357(19) 0.0015(16) 0.0163(16) -0.0004(17) N2 0.035(2) 0.037(2) 0.0309(19) 0.0085(16) 0.0146(16) 0.0021(17) C1 0.043(3) 0.047(3) 0.052(3) 0.009(2) 0.012(2) -0.014(2) C2 0.027(2) 0.032(2) 0.032(2) 0.0009(18) 0.0125(18) 0.0012(19) C3 0.037(3) 0.036(3) 0.045(3) 0.005(2) 0.019(2) 0.002(2) C4 0.039(3) 0.049(3) 0.035(2) 0.012(2) 0.013(2) 0.004(2) C5 0.030(2) 0.054(3) 0.036(2) 0.010(2) 0.0027(19) 0.008(2) C6 0.027(2) 0.042(3) 0.041(2) 0.000(2) 0.009(2) -0.004(2) C7 0.030(2) 0.034(2) 0.033(2) 0.0019(19) 0.0138(19) 0.0056(19) C8 0.023(2) 0.042(3) 0.034(2) 0.005(2) 0.0080(19) 0.000(2) C9 0.021(2) 0.039(3) 0.034(2) 0.002(2) 0.0058(18) -0.0014(19) C10 0.028(2) 0.043(3) 0.043(3) 0.010(2) 0.013(2) -0.005(2) C11 0.034(3) 0.038(3) 0.037(2) 0.010(2) 0.015(2) -0.002(2) C12 0.027(2) 0.039(3) 0.026(2) 0.0049(18) 0.0097(18) 0.0045(19) C13 0.030(2) 0.036(2) 0.028(2) 0.0078(18) 0.0079(18) 0.0026(19) C14 0.033(2) 0.027(2) 0.027(2) 0.0035(18) 0.0120(19) 0.0040(19) C15 0.032(2) 0.032(2) 0.030(2) -0.0009(19) 0.0136(19) 0.0030(19) C16 0.036(2) 0.034(2) 0.033(2) -0.0030(19) 0.0136(19) 0.001(2) C17 0.045(3) 0.034(3) 0.042(3) -0.003(2) 0.022(2) -0.006(2) C18 0.034(3) 0.045(3) 0.045(3) -0.009(2) 0.014(2) -0.011(2) C19 0.035(2) 0.046(3) 0.041(2) -0.004(2) 0.008(2) -0.006(2) C20 0.042(3) 0.040(3) 0.035(2) 0.006(2) 0.011(2) 0.000(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 C2 1.756(4) . ? S1 C1 1.785(4) . ? N1 N2 1.348(4) . ? N1 C14 1.350(4) . ? N2 C12 1.345(4) . ? N2 H2 0.8800 . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? C2 C3 1.385(5) . ? C2 C7 1.418(5) . ? C3 C4 1.383(5) . ? C3 H3 0.9500 . ? C4 C5 1.379(6) . ? C4 H4 0.9500 . ? C5 C6 1.373(5) . ? C5 H5 0.9500 . ? C6 C7 1.411(5) . ? C6 H6 0.9500 . ? C7 C8 1.434(5) . ? C8 C9 1.192(5) . ? C9 C10 1.424(5) . ? C10 C11 1.342(5) . ? C10 H10 0.9500 . ? C11 C12 1.441(5) . ? C11 H11 0.9500 . ? C12 C13 1.394(5) . ? C13 C14 1.391(5) . ? C13 H13 0.9500 . ? C14 C15 1.475(5) . ? C15 C16 1.393(5) . ? C15 C20 1.398(5) . ? C16 C17 1.388(5) . ? C16 H16 0.9500 . ? C17 C18 1.385(5) . ? C17 H17 0.9500 . ? C18 C19 1.371(5) . ? C18 H18 0.9500 . ? C19 C20 1.388(5) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? 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 C2 S1 C1 103.72(19) . . ? N2 N1 C14 107.2(3) . . ? C12 N2 N1 110.6(3) . . ? C12 N2 H2 124.7 . . ? N1 N2 H2 124.7 . . ? S1 C1 H1A 109.5 . . ? S1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? S1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C2 C7 119.5(4) . . ? C3 C2 S1 124.4(3) . . ? C7 C2 S1 116.1(3) . . ? C4 C3 C2 120.5(4) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 120.7(4) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C6 C5 C4 120.0(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.9(4) . . ? C5 C6 H6 119.6 . . ? C7 C6 H6 119.6 . . ? C6 C7 C2 118.4(4) . . ? C6 C7 C8 119.7(4) . . ? C2 C7 C8 121.9(4) . . ? C9 C8 C7 176.7(4) . . ? C8 C9 C10 172.9(4) . . ? C11 C10 C9 128.1(4) . . ? C11 C10 H10 116.0 . . ? C9 C10 H10 116.0 . . ? C10 C11 C12 128.4(4) . . ? C10 C11 H11 115.8 . . ? C12 C11 H11 115.8 . . ? N2 C12 C13 107.3(3) . . ? N2 C12 C11 118.7(3) . . ? C13 C12 C11 134.0(3) . . ? C14 C13 C12 105.7(3) . . ? C14 C13 H13 127.1 . . ? C12 C13 H13 127.1 . . ? N1 C14 C13 109.2(3) . . ? N1 C14 C15 119.9(3) . . ? C13 C14 C15 130.9(3) . . ? C16 C15 C20 118.2(4) . . ? C16 C15 C14 120.4(4) . . ? C20 C15 C14 121.4(4) . . ? C17 C16 C15 120.8(4) . . ? C17 C16 H16 119.6 . . ? C15 C16 H16 119.6 . . ? C18 C17 C16 120.1(4) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 119.7(4) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C18 C19 C20 120.6(4) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C19 C20 C15 120.5(4) . . ? C19 C20 H20 119.8 . . ? C15 C20 H20 119.8 . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.293 _refine_diff_density_min -0.316 _refine_diff_density_rms 0.087 # Attachment '- compound_6i.cif' data_ch13402 _database_code_depnum_ccdc_archive 'CCDC 883589' #TrackingRef '- compound_6i.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H22 N2 O2' _chemical_formula_sum 'C27 H22 N2 O2' _chemical_formula_weight 406.47 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.123(5) _cell_length_b 7.632(4) _cell_length_c 12.700(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.390(10) _cell_angle_gamma 90.00 _cell_volume 1078.0(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 428 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9421 _exptl_absorpt_correction_T_max 0.9719 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6366 _diffrn_reflns_av_R_equivalents 0.0437 _diffrn_reflns_av_sigmaI/netI 0.0668 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 25.02 _reflns_number_total 2970 _reflns_number_gt 2106 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.1583P)^2^+0.3591P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -5(3) _refine_ls_number_reflns 2970 _refine_ls_number_parameters 280 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1896 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 0.789 _refine_ls_restrained_S_all 0.789 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5228(5) -0.2762(11) -0.0698(4) 0.0863(19) Uani 1 1 d . . . H1A H 0.5157 -0.2860 -0.1449 0.129 Uiso 1 1 calc R . . H1B H 0.5643 -0.3768 -0.0424 0.129 Uiso 1 1 calc R . . H1C H 0.5672 -0.1721 -0.0523 0.129 Uiso 1 1 calc R . . C2 C 0.3965(4) -0.2531(7) 0.0836(3) 0.0534(11) Uani 1 1 d . . . C3 C 0.2813(4) -0.2265(6) 0.1232(3) 0.0511(11) Uani 1 1 d . . . H3 H 0.2155 -0.2227 0.0777 0.061 Uiso 1 1 calc R . . C4 C 0.2653(4) -0.2060(6) 0.2297(3) 0.0473(10) Uani 1 1 d . . . H4 H 0.1881 -0.1888 0.2554 0.057 Uiso 1 1 calc R . . C5 C 0.3623(4) -0.2105(6) 0.3006(3) 0.0453(10) Uani 1 1 d . . . C6 C 0.4751(4) -0.2416(7) 0.2601(4) 0.0545(11) Uani 1 1 d . . . H6 H 0.5403 -0.2497 0.3061 0.065 Uiso 1 1 calc R . . C7 C 0.4941(4) -0.2612(8) 0.1531(4) 0.0583(12) Uani 1 1 d . . . H7 H 0.5713 -0.2796 0.1277 0.070 Uiso 1 1 calc R . . C8 C 0.3451(4) -0.1947(6) 0.4163(3) 0.0454(10) Uani 1 1 d . . . C9 C 0.3928(4) -0.3300(6) 0.4838(4) 0.0520(11) Uani 1 1 d . . . H9 H 0.4363 -0.4216 0.4543 0.062 Uiso 1 1 calc R . . C10 C 0.3755(4) -0.3268(6) 0.5895(4) 0.0548(12) Uani 1 1 d . . . H10 H 0.4056 -0.4167 0.6314 0.066 Uiso 1 1 calc R . . C11 C 0.3123(4) -0.1879(6) 0.6351(3) 0.0493(11) Uani 1 1 d . . . C12 C 0.2787(4) -0.1357(7) 0.7360(3) 0.0546(12) Uani 1 1 d . . . H12 H 0.2931 -0.1955 0.7987 0.066 Uiso 1 1 calc R . . C13 C 0.2194(4) 0.0238(7) 0.7242(3) 0.0477(11) Uani 1 1 d . . . C14 C 0.1685(4) 0.1372(7) 0.8081(3) 0.0504(12) Uani 1 1 d . . . C15 C 0.1921(5) 0.1008(8) 0.9142(3) 0.0631(14) Uani 1 1 d . . . H15 H 0.2365 0.0017 0.9320 0.076 Uiso 1 1 calc R . . C16 C 0.1508(5) 0.2090(9) 0.9926(4) 0.0733(16) Uani 1 1 d . . . H16 H 0.1689 0.1840 1.0626 0.088 Uiso 1 1 calc R . . C17 C 0.0833(5) 0.3532(11) 0.9681(4) 0.0806(18) Uani 1 1 d . . . H17 H 0.0562 0.4268 1.0212 0.097 Uiso 1 1 calc R . . C18 C 0.0555(6) 0.3889(11) 0.8649(4) 0.094(2) Uani 1 1 d . . . H18 H 0.0088 0.4861 0.8480 0.113 Uiso 1 1 calc R . . C19 C 0.0974(6) 0.2789(9) 0.7852(4) 0.0815(19) Uani 1 1 d . . . H19 H 0.0767 0.3023 0.7155 0.098 Uiso 1 1 calc R . . C20 C 0.2816(4) -0.0575(6) 0.4596(3) 0.0411(9) Uani 1 1 d . . . C21 C 0.2288(4) 0.0889(6) 0.3979(3) 0.0417(10) Uani 1 1 d . . . C22 C 0.3031(4) 0.2068(6) 0.3438(3) 0.0508(11) Uani 1 1 d . . . H22 H 0.3861 0.1945 0.3487 0.061 Uiso 1 1 calc R . . C23 C 0.2556(5) 0.3401(6) 0.2838(3) 0.0552(12) Uani 1 1 d . . . H23 H 0.3061 0.4173 0.2487 0.066 Uiso 1 1 calc R . . C24 C 0.1326(5) 0.3585(7) 0.2759(3) 0.0584(13) Uani 1 1 d . . . H24 H 0.1004 0.4482 0.2349 0.070 Uiso 1 1 calc R . . C25 C 0.0562(4) 0.2449(6) 0.3283(3) 0.0532(11) Uani 1 1 d . . . H25 H -0.0266 0.2590 0.3223 0.064 Uiso 1 1 calc R . . C26 C 0.1028(4) 0.1105(6) 0.3894(3) 0.0437(10) Uani 1 1 d . . . C27 C -0.0889(4) 0.0302(8) 0.4599(4) 0.0704(15) Uani 1 1 d . . . H27A H -0.1270 -0.0650 0.4961 0.106 Uiso 1 1 calc R . . H27B H -0.1291 0.0499 0.3938 0.106 Uiso 1 1 calc R . . H27C H -0.0934 0.1343 0.5022 0.106 Uiso 1 1 calc R . . N1 N 0.2688(3) -0.0553(5) 0.5689(3) 0.0437(8) Uani 1 1 d . . . N2 N 0.2116(3) 0.0748(5) 0.6222(3) 0.0469(9) Uani 1 1 d . . . O1 O 0.4043(3) -0.2665(7) -0.0242(2) 0.0760(11) Uani 1 1 d . . . O2 O 0.0349(3) -0.0125(4) 0.4413(2) 0.0525(8) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.079(4) 0.116(5) 0.064(3) 0.000(4) 0.020(3) 0.021(4) C2 0.061(3) 0.051(3) 0.048(3) 0.003(2) 0.004(2) 0.009(2) C3 0.049(2) 0.053(3) 0.051(2) 0.004(2) -0.0054(19) 0.010(2) C4 0.044(2) 0.047(3) 0.050(2) 0.003(2) -0.0003(18) 0.003(2) C5 0.045(2) 0.038(2) 0.052(2) -0.0026(19) 0.0000(18) 0.0047(19) C6 0.049(3) 0.053(3) 0.061(3) -0.006(2) -0.006(2) 0.007(2) C7 0.049(3) 0.068(3) 0.059(3) -0.006(3) 0.002(2) 0.010(2) C8 0.039(2) 0.043(2) 0.055(2) 0.002(2) -0.0076(18) 0.0050(19) C9 0.044(2) 0.048(3) 0.065(3) 0.002(2) -0.009(2) 0.011(2) C10 0.052(3) 0.050(3) 0.062(3) 0.008(2) -0.013(2) 0.008(2) C11 0.046(2) 0.050(3) 0.052(2) 0.011(2) -0.0121(19) -0.004(2) C12 0.055(3) 0.062(3) 0.047(2) 0.012(2) -0.010(2) -0.003(2) C13 0.045(2) 0.061(3) 0.038(2) 0.007(2) -0.0054(17) -0.006(2) C14 0.043(2) 0.070(3) 0.038(2) 0.002(2) -0.0055(18) -0.007(2) C15 0.067(3) 0.076(4) 0.047(3) 0.006(3) 0.005(2) -0.005(3) C16 0.074(4) 0.101(5) 0.045(3) -0.001(3) 0.004(2) -0.001(4) C17 0.082(4) 0.106(5) 0.053(3) -0.012(3) 0.007(3) 0.009(4) C18 0.118(5) 0.100(5) 0.063(3) -0.002(4) 0.002(3) 0.046(5) C19 0.099(4) 0.096(5) 0.049(3) -0.001(3) -0.006(3) 0.032(4) C20 0.043(2) 0.040(2) 0.041(2) 0.0000(18) -0.0058(17) 0.0000(18) C21 0.047(2) 0.040(2) 0.039(2) -0.0022(18) -0.0018(17) 0.0065(19) C22 0.052(3) 0.050(3) 0.051(2) -0.001(2) 0.0046(19) 0.003(2) C23 0.071(3) 0.040(2) 0.055(3) 0.006(2) 0.011(2) 0.003(2) C24 0.081(4) 0.048(3) 0.046(2) 0.009(2) 0.004(2) 0.014(3) C25 0.056(3) 0.049(3) 0.055(2) 0.005(2) -0.005(2) 0.014(2) C26 0.047(2) 0.041(2) 0.044(2) 0.0004(19) -0.0031(18) 0.0078(19) C27 0.054(3) 0.074(4) 0.083(4) 0.016(3) 0.013(3) 0.010(3) N1 0.046(2) 0.042(2) 0.0429(19) 0.0014(16) -0.0057(15) 0.0039(16) N2 0.052(2) 0.049(2) 0.0403(19) -0.0018(17) -0.0033(15) 0.0022(18) O1 0.070(2) 0.108(3) 0.0500(19) 0.006(2) 0.0057(15) 0.011(2) O2 0.0456(17) 0.0517(19) 0.0603(18) 0.0160(15) -0.0014(13) 0.0062(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.445(6) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O1 1.377(5) . ? C2 C3 1.394(6) . ? C2 C7 1.396(7) . ? C3 C4 1.374(6) . ? C3 H3 0.9300 . ? C4 C5 1.401(6) . ? C4 H4 0.9300 . ? C5 C6 1.379(6) . ? C5 C8 1.488(6) . ? C6 C7 1.385(6) . ? C6 H6 0.9300 . ? C7 H7 0.9300 . ? C8 C20 1.380(6) . ? C8 C9 1.441(6) . ? C9 C10 1.357(6) . ? C9 H9 0.9300 . ? C10 C11 1.400(7) . ? C10 H10 0.9300 . ? C11 C12 1.395(6) . ? C11 N1 1.401(5) . ? C12 C13 1.392(7) . ? C12 H12 0.9300 . ? C13 N2 1.355(5) . ? C13 C14 1.488(6) . ? C14 C19 1.370(8) . ? C14 C15 1.399(6) . ? C15 C16 1.375(8) . ? C15 H15 0.9300 . ? C16 C17 1.367(9) . ? C16 H16 0.9300 . ? C17 C18 1.372(8) . ? C17 H17 0.9300 . ? C18 C19 1.397(8) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 N1 1.397(5) . ? C20 C21 1.483(6) . ? C21 C22 1.405(6) . ? C21 C26 1.415(6) . ? C22 C23 1.374(7) . ? C22 H22 0.9300 . ? C23 C24 1.378(7) . ? C23 H23 0.9300 . ? C24 C25 1.387(7) . ? C24 H24 0.9300 . ? C25 C26 1.385(6) . ? C25 H25 0.9300 . ? C26 O2 1.376(5) . ? C27 O2 1.436(5) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? N1 N2 1.362(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 O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C3 115.8(4) . . ? O1 C2 C7 124.8(4) . . ? C3 C2 C7 119.4(4) . . ? C4 C3 C2 119.8(4) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 121.7(4) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C6 C5 C4 117.6(4) . . ? C6 C5 C8 120.3(4) . . ? C4 C5 C8 121.9(4) . . ? C5 C6 C7 122.0(4) . . ? C5 C6 H6 119.0 . . ? C7 C6 H6 119.0 . . ? C6 C7 C2 119.5(4) . . ? C6 C7 H7 120.3 . . ? C2 C7 H7 120.3 . . ? C20 C8 C9 119.6(4) . . ? C20 C8 C5 121.7(4) . . ? C9 C8 C5 118.7(4) . . ? C10 C9 C8 121.4(4) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C9 C10 C11 119.9(4) . . ? C9 C10 H10 120.1 . . ? C11 C10 H10 120.1 . . ? C12 C11 N1 104.6(4) . . ? C12 C11 C10 137.3(4) . . ? N1 C11 C10 118.1(4) . . ? C11 C12 C13 106.3(4) . . ? C11 C12 H12 126.9 . . ? C13 C12 H12 126.9 . . ? N2 C13 C12 112.4(4) . . ? N2 C13 C14 119.7(4) . . ? C12 C13 C14 127.9(4) . . ? C19 C14 C15 117.8(5) . . ? C19 C14 C13 122.0(4) . . ? C15 C14 C13 120.3(5) . . ? C16 C15 C14 121.1(5) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C17 C16 C15 120.3(5) . . ? C17 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? C16 C17 C18 119.8(6) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C19 119.9(6) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C14 C19 C18 121.0(5) . . ? C14 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C8 C20 N1 117.5(4) . . ? C8 C20 C21 124.3(3) . . ? N1 C20 C21 118.2(3) . . ? C22 C21 C26 118.3(4) . . ? C22 C21 C20 120.6(4) . . ? C26 C21 C20 121.1(4) . . ? C23 C22 C21 121.4(4) . . ? C23 C22 H22 119.3 . . ? C21 C22 H22 119.3 . . ? C24 C23 C22 119.6(4) . . ? C24 C23 H23 120.2 . . ? C22 C23 H23 120.2 . . ? C23 C24 C25 120.8(4) . . ? C23 C24 H24 119.6 . . ? C25 C24 H24 119.6 . . ? C26 C25 C24 120.3(4) . . ? C26 C25 H25 119.9 . . ? C24 C25 H25 119.9 . . ? O2 C26 C25 124.7(4) . . ? O2 C26 C21 115.5(4) . . ? C25 C26 C21 119.7(4) . . ? O2 C27 H27A 109.5 . . ? O2 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O2 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? N2 N1 C20 123.7(3) . . ? N2 N1 C11 112.9(3) . . ? C20 N1 C11 123.4(4) . . ? C13 N2 N1 103.8(4) . . ? C2 O1 C1 117.8(4) . . ? C26 O2 C27 117.0(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.231 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.082