# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Weiqing Xie' _publ_contact_author_email 'xiewq@mail.sioc.ac.cn, xiewq@mai.sioc.ac.cn' loop_ _publ_author_name 'Feng Fan' 'Weiqing Xie' 'Dawei Ma' data_cd211522 _database_code_depnum_ccdc_archive 'CCDC 879839' #TrackingRef '- 5d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H21 N3 O4' _chemical_formula_weight 391.42 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 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 13.4875(9) _cell_length_b 10.5732(7) _cell_length_c 13.9427(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.886(2) _cell_angle_gamma 90.00 _cell_volume 1930.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3540 _cell_measurement_theta_min 4.889 _cell_measurement_theta_max 51.525 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.165 _exptl_crystal_size_mid 0.123 _exptl_crystal_size_min 0.112 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.347 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.86561 _exptl_absorpt_correction_T_max 1.00000 _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_% ? _diffrn_reflns_number 11475 _diffrn_reflns_av_R_equivalents 0.0223 _diffrn_reflns_av_sigmaI/netI 0.0268 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3797 _reflns_number_gt 3057 _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^)+(0.0500P)^2^+0.4621P] 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 3797 _refine_ls_number_parameters 267 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0520 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1095 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 N1 N 0.54404(10) 0.82429(13) -0.12802(10) 0.0464(3) Uani 1 1 d . . . N2 N 0.66286(9) 0.67562(11) -0.02527(9) 0.0371(3) Uani 1 1 d . . . N3 N 0.72419(9) 0.87995(12) 0.21433(9) 0.0419(3) Uani 1 1 d . . . O1 O 0.83450(8) 0.62168(10) 0.02605(9) 0.0508(3) Uani 1 1 d . . . O2 O 0.86381(9) 0.76083(12) 0.21867(8) 0.0577(3) Uani 1 1 d . . . O3 O 0.52346(9) 0.55796(11) -0.09509(10) 0.0603(3) Uani 1 1 d . . . O4 O 0.67880(9) 0.46806(10) -0.05384(9) 0.0527(3) Uani 1 1 d . . . C1 C 0.60463(12) 0.90159(15) -0.17059(11) 0.0443(4) Uani 1 1 d . . . C2 C 0.58901(16) 0.9389(2) -0.26825(13) 0.0661(5) Uani 1 1 d . . . H2 H 0.5343 0.9080 -0.3165 0.079 Uiso 1 1 calc R . . C3 C 0.65743(19) 1.0235(3) -0.29148(16) 0.0824(7) Uani 1 1 d . . . H3 H 0.6485 1.0496 -0.3567 0.099 Uiso 1 1 calc R . . C4 C 0.73882(18) 1.0705(2) -0.22071(18) 0.0766(6) Uani 1 1 d . . . H4 H 0.7839 1.1272 -0.2387 0.092 Uiso 1 1 calc R . . C5 C 0.75383(13) 1.03323(16) -0.12213(14) 0.0540(4) Uani 1 1 d . . . H5 H 0.8078 1.0654 -0.0738 0.065 Uiso 1 1 calc R . . C6 C 0.68679(11) 0.94787(14) -0.09842(11) 0.0396(3) Uani 1 1 d . . . C7 C 0.67915(10) 0.89745(13) 0.00154(10) 0.0337(3) Uani 1 1 d . . . C8 C 0.59874(10) 0.79072(13) -0.03057(11) 0.0365(3) Uani 1 1 d . . . H8 H 0.5531 0.7848 0.0144 0.044 Uiso 1 1 calc R . . C9 C 0.76600(10) 0.69569(13) 0.01904(10) 0.0349(3) Uani 1 1 d . . . C10 C 0.77534(10) 0.83032(13) 0.05926(10) 0.0336(3) Uani 1 1 d . . . H10 H 0.8353 0.8705 0.0443 0.040 Uiso 1 1 calc R . . C11 C 0.79096(11) 0.82147(14) 0.17193(10) 0.0382(3) Uani 1 1 d . . . C12 C 0.63572(12) 0.95394(16) 0.16253(12) 0.0469(4) Uani 1 1 d . . . H12A H 0.6269 1.0256 0.2032 0.056 Uiso 1 1 calc R . . H12B H 0.5749 0.9019 0.1527 0.056 Uiso 1 1 calc R . . C13 C 0.64731(11) 1.00120(14) 0.06379(11) 0.0400(3) Uani 1 1 d . . . H13A H 0.6981 1.0680 0.0744 0.048 Uiso 1 1 calc R . . H13B H 0.5829 1.0371 0.0278 0.048 Uiso 1 1 calc R . . C14 C 0.61413(12) 0.56279(14) -0.06167(11) 0.0417(3) Uani 1 1 d . . . C15 C 0.63671(17) 0.34797(17) -0.09241(17) 0.0752(6) Uani 1 1 d . . . H15A H 0.5719 0.3356 -0.0767 0.113 Uiso 1 1 calc R . . H15B H 0.6825 0.2813 -0.0634 0.113 Uiso 1 1 calc R . . H15C H 0.6277 0.3470 -0.1628 0.113 Uiso 1 1 calc R . . C16 C 0.73448(13) 0.86642(17) 0.32090(11) 0.0497(4) Uani 1 1 d . . . H16A H 0.7298 0.9493 0.3493 0.060 Uiso 1 1 calc R . . H16B H 0.8015 0.8323 0.3509 0.060 Uiso 1 1 calc R . . C17 C 0.65414(11) 0.78133(15) 0.34538(11) 0.0425(4) Uani 1 1 d . . . C18 C 0.60741(13) 0.81491(17) 0.41949(13) 0.0536(4) Uani 1 1 d . . . H18 H 0.6247 0.8909 0.4530 0.064 Uiso 1 1 calc R . . C19 C 0.53534(15) 0.7372(2) 0.44457(16) 0.0694(5) Uani 1 1 d . . . H19 H 0.5046 0.7608 0.4948 0.083 Uiso 1 1 calc R . . C20 C 0.50903(15) 0.6249(2) 0.39522(17) 0.0714(6) Uani 1 1 d . . . H20 H 0.4605 0.5725 0.4120 0.086 Uiso 1 1 calc R . . C21 C 0.55470(15) 0.59029(18) 0.32101(15) 0.0653(5) Uani 1 1 d . . . H21 H 0.5369 0.5145 0.2875 0.078 Uiso 1 1 calc R . . C22 C 0.62664(13) 0.66756(17) 0.29631(13) 0.0531(4) Uani 1 1 d . . . H22 H 0.6573 0.6434 0.2461 0.064 Uiso 1 1 calc R . . H1 H 0.5006(14) 0.7729(18) -0.1614(14) 0.059(5) 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 N1 0.0418(7) 0.0450(7) 0.0416(8) -0.0027(6) -0.0109(6) 0.0023(6) N2 0.0376(6) 0.0332(6) 0.0368(7) -0.0024(5) 0.0019(5) 0.0026(5) N3 0.0419(7) 0.0490(7) 0.0313(6) -0.0026(6) 0.0017(5) 0.0034(6) O1 0.0428(6) 0.0437(6) 0.0616(7) -0.0075(5) 0.0043(5) 0.0132(5) O2 0.0538(7) 0.0674(8) 0.0414(6) 0.0009(6) -0.0090(5) 0.0232(6) O3 0.0494(7) 0.0505(7) 0.0709(8) -0.0082(6) -0.0056(6) -0.0063(5) O4 0.0593(7) 0.0334(6) 0.0585(7) -0.0057(5) 0.0005(6) 0.0025(5) C1 0.0466(8) 0.0470(8) 0.0356(8) 0.0000(7) 0.0023(7) 0.0148(7) C2 0.0725(12) 0.0833(14) 0.0379(9) 0.0039(9) 0.0041(9) 0.0225(11) C3 0.0934(16) 0.1091(19) 0.0483(11) 0.0296(12) 0.0241(12) 0.0312(15) C4 0.0779(14) 0.0813(14) 0.0803(15) 0.0345(12) 0.0379(12) 0.0146(12) C5 0.0496(9) 0.0515(10) 0.0618(11) 0.0137(8) 0.0150(8) 0.0072(8) C6 0.0410(8) 0.0390(8) 0.0376(8) 0.0047(6) 0.0071(6) 0.0117(6) C7 0.0321(7) 0.0334(7) 0.0322(7) 0.0002(6) 0.0009(6) 0.0036(5) C8 0.0330(7) 0.0366(7) 0.0371(8) -0.0021(6) 0.0030(6) 0.0047(6) C9 0.0364(7) 0.0366(7) 0.0300(7) 0.0005(6) 0.0048(6) 0.0043(6) C10 0.0303(7) 0.0346(7) 0.0335(7) 0.0000(6) 0.0032(6) 0.0034(5) C11 0.0373(7) 0.0377(7) 0.0341(8) -0.0029(6) -0.0026(6) 0.0012(6) C12 0.0431(8) 0.0543(9) 0.0408(8) -0.0080(7) 0.0052(7) 0.0120(7) C13 0.0373(7) 0.0371(7) 0.0406(8) -0.0036(6) -0.0006(6) 0.0086(6) C14 0.0490(9) 0.0379(8) 0.0345(8) -0.0011(6) 0.0030(7) -0.0013(7) C15 0.0873(14) 0.0360(9) 0.0870(15) -0.0128(9) -0.0089(12) -0.0005(9) C16 0.0534(9) 0.0604(10) 0.0314(8) -0.0051(7) 0.0025(7) -0.0044(8) C17 0.0428(8) 0.0443(8) 0.0351(8) -0.0003(7) -0.0009(6) 0.0047(7) C18 0.0578(10) 0.0520(10) 0.0508(10) -0.0052(8) 0.0127(8) 0.0008(8) C19 0.0621(11) 0.0809(14) 0.0694(13) -0.0009(11) 0.0240(10) -0.0034(11) C20 0.0584(11) 0.0747(14) 0.0763(14) 0.0133(12) 0.0066(10) -0.0162(10) C21 0.0695(12) 0.0477(10) 0.0652(12) 0.0011(9) -0.0104(10) -0.0071(9) C22 0.0577(10) 0.0501(9) 0.0462(9) -0.0054(8) 0.0019(8) 0.0047(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C1 1.386(2) . ? N1 C8 1.4266(19) . ? N1 H1 0.851(19) . ? N2 C9 1.3963(18) . ? N2 C14 1.3974(18) . ? N2 C8 1.4844(17) . ? N3 C11 1.3411(19) . ? N3 C12 1.4642(19) . ? N3 C16 1.4658(19) . ? O1 C9 1.1967(16) . ? O2 C11 1.2222(17) . ? O3 C14 1.2008(18) . ? O4 C14 1.3153(18) . ? O4 C15 1.441(2) . ? C1 C2 1.384(2) . ? C1 C6 1.395(2) . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 C4 1.381(3) . ? C3 H3 0.9300 . ? C4 C5 1.397(3) . ? C4 H4 0.9300 . ? C5 C6 1.373(2) . ? C5 H5 0.9300 . ? C6 C7 1.519(2) . ? C7 C13 1.5231(19) . ? C7 C10 1.5276(18) . ? C7 C8 1.5547(19) . ? C8 H8 0.9800 . ? C9 C10 1.5241(19) . ? C10 C11 1.537(2) . ? C10 H10 0.9800 . ? C12 C13 1.508(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.509(2) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.380(2) . ? C17 C22 1.390(2) . ? C18 C19 1.380(3) . ? C18 H18 0.9300 . ? C19 C20 1.376(3) . ? C19 H19 0.9300 . ? C20 C21 1.375(3) . ? C20 H20 0.9300 . ? C21 C22 1.374(3) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 N1 C8 109.34(12) . . ? C1 N1 H1 122.7(13) . . ? C8 N1 H1 119.6(13) . . ? C9 N2 C14 128.48(12) . . ? C9 N2 C8 113.84(11) . . ? C14 N2 C8 117.66(11) . . ? C11 N3 C12 125.65(12) . . ? C11 N3 C16 119.45(13) . . ? C12 N3 C16 114.82(12) . . ? C14 O4 C15 116.48(13) . . ? C2 C1 N1 128.54(16) . . ? C2 C1 C6 121.11(17) . . ? N1 C1 C6 110.25(13) . . ? C3 C2 C1 117.62(19) . . ? C3 C2 H2 121.2 . . ? C1 C2 H2 121.2 . . ? C2 C3 C4 121.87(19) . . ? C2 C3 H3 119.1 . . ? C4 C3 H3 119.1 . . ? C3 C4 C5 120.3(2) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 118.29(19) . . ? C6 C5 H5 120.9 . . ? C4 C5 H5 120.9 . . ? C5 C6 C1 120.81(15) . . ? C5 C6 C7 130.20(15) . . ? C1 C6 C7 108.77(13) . . ? C6 C7 C13 111.14(12) . . ? C6 C7 C10 114.24(11) . . ? C13 C7 C10 110.75(11) . . ? C6 C7 C8 100.77(11) . . ? C13 C7 C8 114.48(11) . . ? C10 C7 C8 105.07(11) . . ? N1 C8 N2 114.41(12) . . ? N1 C8 C7 105.03(12) . . ? N2 C8 C7 102.88(10) . . ? N1 C8 H8 111.3 . . ? N2 C8 H8 111.3 . . ? C7 C8 H8 111.3 . . ? O1 C9 N2 127.19(13) . . ? O1 C9 C10 125.92(13) . . ? N2 C9 C10 106.87(11) . . ? C9 C10 C7 104.80(11) . . ? C9 C10 C11 107.35(11) . . ? C7 C10 C11 117.23(11) . . ? C9 C10 H10 109.1 . . ? C7 C10 H10 109.1 . . ? C11 C10 H10 109.1 . . ? O2 C11 N3 123.07(14) . . ? O2 C11 C10 118.20(13) . . ? N3 C11 C10 118.73(12) . . ? N3 C12 C13 112.13(12) . . ? N3 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? N3 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C7 112.76(12) . . ? C12 C13 H13A 109.0 . . ? C7 C13 H13A 109.0 . . ? C12 C13 H13B 109.0 . . ? C7 C13 H13B 109.0 . . ? H13A C13 H13B 107.8 . . ? O3 C14 O4 126.39(14) . . ? O3 C14 N2 121.57(14) . . ? O4 C14 N2 112.04(12) . . ? O4 C15 H15A 109.5 . . ? O4 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O4 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 C17 112.89(13) . . ? N3 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? N3 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C18 C17 C22 118.40(16) . . ? C18 C17 C16 119.85(15) . . ? C22 C17 C16 121.74(15) . . ? C17 C18 C19 120.83(17) . . ? C17 C18 H18 119.6 . . ? C19 C18 H18 119.6 . . ? C20 C19 C18 120.00(19) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C21 C20 C19 119.85(19) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C22 C21 C20 120.09(18) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C17 120.82(17) . . ? C21 C22 H22 119.6 . . ? C17 C22 H22 119.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 N1 C1 C2 168.47(16) . . . . ? C8 N1 C1 C6 -15.19(17) . . . . ? N1 C1 C2 C3 175.89(17) . . . . ? C6 C1 C2 C3 -0.1(3) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.2(3) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? C4 C5 C6 C1 -1.3(2) . . . . ? C4 C5 C6 C7 -175.25(16) . . . . ? C2 C1 C6 C5 0.9(2) . . . . ? N1 C1 C6 C5 -175.78(13) . . . . ? C2 C1 C6 C7 176.00(14) . . . . ? N1 C1 C6 C7 -0.66(17) . . . . ? C5 C6 C7 C13 67.12(19) . . . . ? C1 C6 C7 C13 -107.39(14) . . . . ? C5 C6 C7 C10 -59.1(2) . . . . ? C1 C6 C7 C10 126.40(13) . . . . ? C5 C6 C7 C8 -171.16(15) . . . . ? C1 C6 C7 C8 14.33(14) . . . . ? C1 N1 C8 N2 -88.10(15) . . . . ? C1 N1 C8 C7 23.94(15) . . . . ? C9 N2 C8 N1 122.64(13) . . . . ? C14 N2 C8 N1 -58.94(17) . . . . ? C9 N2 C8 C7 9.31(15) . . . . ? C14 N2 C8 C7 -172.26(12) . . . . ? C6 C7 C8 N1 -22.54(13) . . . . ? C13 C7 C8 N1 96.80(14) . . . . ? C10 C7 C8 N1 -141.49(12) . . . . ? C6 C7 C8 N2 97.49(12) . . . . ? C13 C7 C8 N2 -143.18(12) . . . . ? C10 C7 C8 N2 -21.46(13) . . . . ? C14 N2 C9 O1 7.6(2) . . . . ? C8 N2 C9 O1 -174.21(14) . . . . ? C14 N2 C9 C10 -171.32(13) . . . . ? C8 N2 C9 C10 6.89(15) . . . . ? O1 C9 C10 C7 160.59(14) . . . . ? N2 C9 C10 C7 -20.49(14) . . . . ? O1 C9 C10 C11 -74.07(18) . . . . ? N2 C9 C10 C11 104.85(12) . . . . ? C6 C7 C10 C9 -83.69(14) . . . . ? C13 C7 C10 C9 149.90(12) . . . . ? C8 C7 C10 C9 25.79(14) . . . . ? C6 C7 C10 C11 157.44(12) . . . . ? C13 C7 C10 C11 31.03(17) . . . . ? C8 C7 C10 C11 -93.08(14) . . . . ? C12 N3 C11 O2 179.93(15) . . . . ? C16 N3 C11 O2 -3.3(2) . . . . ? C12 N3 C11 C10 -0.3(2) . . . . ? C16 N3 C11 C10 176.48(13) . . . . ? C9 C10 C11 O2 57.68(17) . . . . ? C7 C10 C11 O2 175.17(13) . . . . ? C9 C10 C11 N3 -122.09(14) . . . . ? C7 C10 C11 N3 -4.59(19) . . . . ? C11 N3 C12 C13 -22.2(2) . . . . ? C16 N3 C12 C13 160.92(13) . . . . ? N3 C12 C13 C7 49.28(17) . . . . ? C6 C7 C13 C12 178.24(12) . . . . ? C10 C7 C13 C12 -53.65(16) . . . . ? C8 C7 C13 C12 64.91(16) . . . . ? C15 O4 C14 O3 2.3(3) . . . . ? C15 O4 C14 N2 -177.97(15) . . . . ? C9 N2 C14 O3 177.27(15) . . . . ? C8 N2 C14 O3 -0.9(2) . . . . ? C9 N2 C14 O4 -2.5(2) . . . . ? C8 N2 C14 O4 179.39(12) . . . . ? C11 N3 C16 C17 -106.52(16) . . . . ? C12 N3 C16 C17 70.61(18) . . . . ? N3 C16 C17 C18 -137.74(16) . . . . ? N3 C16 C17 C22 43.5(2) . . . . ? C22 C17 C18 C19 0.2(3) . . . . ? C16 C17 C18 C19 -178.59(17) . . . . ? C17 C18 C19 C20 -0.2(3) . . . . ? C18 C19 C20 C21 0.0(3) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C20 C21 C22 C17 -0.1(3) . . . . ? C18 C17 C22 C21 0.0(2) . . . . ? C16 C17 C22 C21 178.75(16) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O3 0.851(19) 2.445(19) 2.8772(19) 112.2(15) . N1 H1 O2 0.851(19) 2.20(2) 2.9655(17) 149.4(17) 4_575 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.211 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.036 # Attachment '- 5s.cif' data_cd212115 _database_code_depnum_ccdc_archive 'CCDC 879840' #TrackingRef '- 5s.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H35 N3 O5 S' _chemical_formula_weight 621.73 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 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 10.4770(6) _cell_length_b 11.2649(7) _cell_length_c 27.4274(16) _cell_angle_alpha 90.00 _cell_angle_beta 100.4940(10) _cell_angle_gamma 90.00 _cell_volume 3182.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3566 _cell_measurement_theta_min 4.482 _cell_measurement_theta_max 48.844 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.321 _exptl_crystal_size_mid 0.213 _exptl_crystal_size_min 0.146 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.297 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1312 _exptl_absorpt_coefficient_mu 0.149 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.42722 _exptl_absorpt_correction_T_max 1.00000 _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_% ? _diffrn_reflns_number 18279 _diffrn_reflns_av_R_equivalents 0.0359 _diffrn_reflns_av_sigmaI/netI 0.0411 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 26.00 _reflns_number_total 6245 _reflns_number_gt 4803 _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^)+(0.0647P)^2^+0.8862P] 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 6245 _refine_ls_number_parameters 413 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0702 _refine_ls_R_factor_gt 0.0522 _refine_ls_wR_factor_ref 0.1366 _refine_ls_wR_factor_gt 0.1267 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.024 _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 0.56344(5) 0.61478(5) 0.090823(18) 0.03534(15) Uani 1 1 d . . . N1 N 0.2852(2) 0.5646(2) 0.01557(7) 0.0482(5) Uani 1 1 d . . . N2 N 0.40837(16) 0.62567(15) 0.09597(6) 0.0365(4) Uani 1 1 d . . . N3 N 0.21865(18) 0.45322(17) 0.17059(6) 0.0454(5) Uani 1 1 d . . . O1 O 0.42293(14) 0.78659(14) 0.14793(6) 0.0459(4) Uani 1 1 d . . . O2 O 0.33355(16) 0.59804(15) 0.21534(6) 0.0531(4) Uani 1 1 d . . . O3 O 0.64027(14) 0.62199(14) 0.13884(6) 0.0488(4) Uani 1 1 d . . . O4 O 0.56642(14) 0.50902(13) 0.06209(5) 0.0437(4) Uani 1 1 d . . . O5 O 0.1025(3) 0.7637(3) 0.83090(10) 0.1218(10) Uani 1 1 d . . . C1 C 0.1950(2) 0.6523(2) 0.00168(8) 0.0397(5) Uani 1 1 d . . . C2 C 0.1633(2) 0.7086(2) -0.04365(8) 0.0499(6) Uani 1 1 d . . . H2 H 0.2084 0.6923 -0.0691 0.060 Uiso 1 1 calc R . . C3 C 0.0634(3) 0.7893(2) -0.05008(9) 0.0595(7) Uani 1 1 d . . . H3 H 0.0421 0.8295 -0.0801 0.071 Uiso 1 1 calc R . . C4 C -0.0058(3) 0.8117(2) -0.01291(10) 0.0620(7) Uani 1 1 d . . . H4 H -0.0742 0.8656 -0.0184 0.074 Uiso 1 1 calc R . . C5 C 0.0254(2) 0.7547(2) 0.03266(9) 0.0495(6) Uani 1 1 d . . . H5 H -0.0225 0.7686 0.0575 0.059 Uiso 1 1 calc R . . C6 C 0.1287(2) 0.67728(19) 0.04016(7) 0.0376(5) Uani 1 1 d . . . C7 C 0.18060(19) 0.59541(18) 0.08378(7) 0.0348(5) Uani 1 1 d . . . C8 C 0.30573(19) 0.54708(19) 0.06757(7) 0.0357(5) Uani 1 1 d . . . H8 H 0.3208 0.4633 0.0764 0.043 Uiso 1 1 calc R . . C9 C 0.3630(2) 0.70344(18) 0.12857(7) 0.0356(5) Uani 1 1 d . . . C10 C 0.22945(19) 0.65622(19) 0.13452(7) 0.0354(5) Uani 1 1 d . . . C11 C 0.2646(2) 0.5648(2) 0.17727(7) 0.0389(5) Uani 1 1 d . . . C12 C 0.1390(2) 0.4045(2) 0.12572(8) 0.0511(6) Uani 1 1 d . . . H12A H 0.0683 0.3593 0.1350 0.061 Uiso 1 1 calc R . . H12B H 0.1914 0.3503 0.1102 0.061 Uiso 1 1 calc R . . C13 C 0.0833(2) 0.4979(2) 0.08850(8) 0.0445(5) Uani 1 1 d . . . H13A H 0.0074 0.5329 0.0985 0.053 Uiso 1 1 calc R . . H13B H 0.0556 0.4608 0.0564 0.053 Uiso 1 1 calc R . . C14 C 0.1384(2) 0.7488(2) 0.14950(7) 0.0395(5) Uani 1 1 d . . . C15 C 0.0379(2) 0.7125(3) 0.17268(9) 0.0546(6) Uani 1 1 d . . . H15 H 0.0307 0.6329 0.1809 0.066 Uiso 1 1 calc R . . C16 C -0.0514(3) 0.7932(4) 0.18370(12) 0.0767(9) Uani 1 1 d . . . H16 H -0.1195 0.7674 0.1985 0.092 Uiso 1 1 calc R . . C17 C -0.0410(3) 0.9102(4) 0.17312(12) 0.0810(10) Uani 1 1 d . . . H17 H -0.1020 0.9640 0.1805 0.097 Uiso 1 1 calc R . . C18 C 0.0596(3) 0.9487(3) 0.15153(11) 0.0683(8) Uani 1 1 d . . . H18 H 0.0681 1.0289 0.1449 0.082 Uiso 1 1 calc R . . C19 C 0.1485(2) 0.8677(2) 0.13965(9) 0.0515(6) Uani 1 1 d . . . H19 H 0.2162 0.8942 0.1247 0.062 Uiso 1 1 calc R . . C20 C 0.2669(3) 0.3642(2) 0.20862(9) 0.0554(6) Uani 1 1 d . . . H20A H 0.1944 0.3187 0.2162 0.066 Uiso 1 1 calc R . . H20B H 0.3085 0.4039 0.2387 0.066 Uiso 1 1 calc R . . C21 C 0.3624(3) 0.2815(2) 0.19134(8) 0.0519(6) Uani 1 1 d . . . C22 C 0.3475(3) 0.1604(3) 0.19381(10) 0.0706(8) Uani 1 1 d . . . H22 H 0.2778 0.1291 0.2063 0.085 Uiso 1 1 calc R . . C23 C 0.4356(5) 0.0853(3) 0.17786(14) 0.0971(13) Uani 1 1 d . . . H23 H 0.4256 0.0035 0.1798 0.117 Uiso 1 1 calc R . . C24 C 0.5374(5) 0.1313(5) 0.15926(14) 0.1048(15) Uani 1 1 d . . . H24 H 0.5963 0.0807 0.1482 0.126 Uiso 1 1 calc R . . C25 C 0.5534(3) 0.2524(4) 0.15675(12) 0.0859(10) Uani 1 1 d . . . H25 H 0.6230 0.2835 0.1442 0.103 Uiso 1 1 calc R . . C26 C 0.4671(3) 0.3258(3) 0.17272(10) 0.0641(7) Uani 1 1 d . . . H26 H 0.4785 0.4075 0.1711 0.077 Uiso 1 1 calc R . . C27 C 0.59765(19) 0.73663(18) 0.05562(7) 0.0366(5) Uani 1 1 d . . . C28 C 0.6562(2) 0.8365(2) 0.07885(9) 0.0498(6) Uani 1 1 d . . . H28 H 0.6766 0.8402 0.1133 0.060 Uiso 1 1 calc R . . C29 C 0.6840(2) 0.9303(2) 0.05055(10) 0.0560(6) Uani 1 1 d . . . H29 H 0.7238 0.9974 0.0662 0.067 Uiso 1 1 calc R . . C30 C 0.6544(2) 0.9274(2) -0.00051(9) 0.0471(6) Uani 1 1 d . . . C31 C 0.5964(2) 0.8261(2) -0.02275(9) 0.0531(6) Uani 1 1 d . . . H31 H 0.5762 0.8223 -0.0572 0.064 Uiso 1 1 calc R . . C32 C 0.5679(2) 0.7307(2) 0.00459(8) 0.0477(6) Uani 1 1 d . . . H32 H 0.5291 0.6632 -0.0111 0.057 Uiso 1 1 calc R . . C33 C 0.6830(3) 1.0305(2) -0.03162(11) 0.0646(7) Uani 1 1 d . . . H33A H 0.6513 1.1024 -0.0193 0.097 Uiso 1 1 calc R . . H33B H 0.6409 1.0184 -0.0654 0.097 Uiso 1 1 calc R . . H33C H 0.7750 1.0366 -0.0301 0.097 Uiso 1 1 calc R . . C34 C 0.1386(4) 0.8078(5) 0.75313(13) 0.1254(17) Uani 1 1 d . . . H34A H 0.0836 0.8755 0.7545 0.188 Uiso 1 1 calc R . . H34B H 0.1156 0.7700 0.7214 0.188 Uiso 1 1 calc R . . H34C H 0.2275 0.8331 0.7579 0.188 Uiso 1 1 calc R . . C35 C 0.1222(3) 0.7244(4) 0.79195(13) 0.0900(11) Uani 1 1 d . . . C36 C 0.1347(7) 0.5980(5) 0.7841(3) 0.202(3) Uani 1 1 d . . . H36A H 0.1334 0.5564 0.8145 0.303 Uiso 1 1 calc R . . H36B H 0.2152 0.5825 0.7732 0.303 Uiso 1 1 calc R . . H36C H 0.0638 0.5714 0.7592 0.303 Uiso 1 1 calc R . . H1 H 0.333(2) 0.534(2) -0.0009(9) 0.049(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 0.0347(3) 0.0391(3) 0.0330(3) -0.0005(2) 0.0082(2) 0.0007(2) N1 0.0499(12) 0.0645(14) 0.0315(10) -0.0071(9) 0.0104(9) 0.0092(10) N2 0.0360(9) 0.0394(10) 0.0355(9) -0.0054(7) 0.0107(7) -0.0039(7) N3 0.0536(11) 0.0452(11) 0.0371(10) 0.0058(8) 0.0077(8) -0.0062(9) O1 0.0465(9) 0.0426(9) 0.0502(9) -0.0127(7) 0.0131(7) -0.0084(7) O2 0.0628(11) 0.0571(10) 0.0358(8) 0.0013(7) -0.0010(8) -0.0051(8) O3 0.0429(9) 0.0624(11) 0.0392(8) 0.0036(7) 0.0020(7) 0.0020(7) O4 0.0479(9) 0.0400(9) 0.0469(9) -0.0036(7) 0.0183(7) 0.0019(7) O5 0.137(2) 0.167(3) 0.0725(16) 0.0013(17) 0.0471(16) -0.004(2) C1 0.0407(12) 0.0438(13) 0.0333(11) -0.0026(9) 0.0031(9) -0.0079(10) C2 0.0558(14) 0.0598(15) 0.0325(11) 0.0005(11) 0.0043(10) -0.0132(12) C3 0.0732(18) 0.0566(16) 0.0413(14) 0.0105(12) -0.0088(12) -0.0099(14) C4 0.0616(16) 0.0599(17) 0.0573(16) 0.0055(13) -0.0080(13) 0.0096(13) C5 0.0460(13) 0.0574(15) 0.0430(13) -0.0003(11) 0.0024(10) 0.0054(11) C6 0.0379(11) 0.0407(12) 0.0336(11) 0.0015(9) 0.0050(9) -0.0049(9) C7 0.0355(11) 0.0400(12) 0.0292(10) -0.0009(9) 0.0068(8) -0.0028(9) C8 0.0393(11) 0.0357(11) 0.0316(10) -0.0038(9) 0.0052(8) -0.0033(9) C9 0.0401(11) 0.0357(11) 0.0318(10) -0.0005(9) 0.0086(9) -0.0001(9) C10 0.0365(11) 0.0399(11) 0.0310(10) -0.0007(9) 0.0097(8) -0.0015(9) C11 0.0391(11) 0.0466(13) 0.0323(11) 0.0008(9) 0.0105(9) -0.0019(10) C12 0.0579(15) 0.0503(14) 0.0449(13) 0.0035(11) 0.0087(11) -0.0164(12) C13 0.0433(13) 0.0508(14) 0.0396(12) -0.0003(10) 0.0080(10) -0.0108(10) C14 0.0387(11) 0.0489(13) 0.0304(10) -0.0037(9) 0.0053(8) 0.0028(10) C15 0.0477(14) 0.0687(17) 0.0505(14) -0.0004(12) 0.0169(11) 0.0038(12) C16 0.0522(16) 0.109(3) 0.075(2) -0.0114(19) 0.0278(14) 0.0111(17) C17 0.0615(19) 0.097(3) 0.082(2) -0.0244(19) 0.0071(16) 0.0307(18) C18 0.0715(19) 0.0575(17) 0.0701(18) -0.0049(14) -0.0023(15) 0.0212(15) C19 0.0529(14) 0.0511(15) 0.0498(14) 0.0000(11) 0.0077(11) 0.0079(11) C20 0.0706(17) 0.0529(15) 0.0434(13) 0.0133(11) 0.0123(12) -0.0046(13) C21 0.0651(16) 0.0477(14) 0.0379(12) 0.0076(11) -0.0036(11) -0.0038(12) C22 0.099(2) 0.0495(16) 0.0553(16) 0.0039(13) -0.0064(15) -0.0095(16) C23 0.143(4) 0.058(2) 0.075(2) -0.0123(18) -0.023(2) 0.020(2) C24 0.117(3) 0.120(4) 0.065(2) -0.023(2) -0.017(2) 0.059(3) C25 0.071(2) 0.114(3) 0.068(2) 0.001(2) -0.0005(16) 0.022(2) C26 0.0607(17) 0.0684(18) 0.0606(17) 0.0074(14) 0.0046(13) 0.0030(14) C27 0.0328(10) 0.0402(12) 0.0378(11) -0.0012(9) 0.0090(8) -0.0018(9) C28 0.0536(14) 0.0548(15) 0.0406(12) -0.0056(11) 0.0072(10) -0.0173(12) C29 0.0615(16) 0.0481(14) 0.0582(15) -0.0065(12) 0.0104(12) -0.0225(12) C30 0.0401(12) 0.0459(13) 0.0565(14) 0.0066(11) 0.0119(10) -0.0050(10) C31 0.0635(16) 0.0556(15) 0.0401(13) 0.0035(11) 0.0091(11) -0.0094(12) C32 0.0594(14) 0.0434(13) 0.0400(12) -0.0024(10) 0.0078(10) -0.0117(11) C33 0.0612(16) 0.0557(16) 0.0778(19) 0.0196(14) 0.0150(14) -0.0114(13) C34 0.103(3) 0.214(5) 0.059(2) 0.027(3) 0.016(2) 0.047(3) C35 0.0574(18) 0.151(4) 0.063(2) -0.012(2) 0.0152(15) -0.010(2) C36 0.210(7) 0.128(5) 0.255(8) -0.049(5) 0.008(6) -0.050(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 O3 1.4152(15) . ? S1 O4 1.4319(15) . ? S1 N2 1.6608(17) . ? S1 C27 1.752(2) . ? N1 C1 1.373(3) . ? N1 C8 1.417(3) . ? N1 H1 0.81(3) . ? N2 C9 1.395(3) . ? N2 C8 1.497(3) . ? N3 C11 1.347(3) . ? N3 C12 1.462(3) . ? N3 C20 1.469(3) . ? O1 C9 1.197(2) . ? O2 C11 1.216(2) . ? O5 C35 1.208(4) . ? C1 C2 1.381(3) . ? C1 C6 1.394(3) . ? C2 C3 1.374(4) . ? C2 H2 0.9300 . ? C3 C4 1.378(4) . ? C3 H3 0.9300 . ? C4 C5 1.390(3) . ? C4 H4 0.9300 . ? C5 C6 1.376(3) . ? C5 H5 0.9300 . ? C6 C7 1.530(3) . ? C7 C13 1.520(3) . ? C7 C10 1.552(3) . ? C7 C8 1.557(3) . ? C8 H8 0.9800 . ? C9 C10 1.533(3) . ? C10 C14 1.519(3) . ? C10 C11 1.553(3) . ? C12 C13 1.508(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C19 1.375(3) . ? C14 C15 1.388(3) . ? C15 C16 1.377(4) . ? C15 H15 0.9300 . ? C16 C17 1.357(5) . ? C16 H16 0.9300 . ? C17 C18 1.370(5) . ? C17 H17 0.9300 . ? C18 C19 1.385(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 C21 1.506(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.376(4) . ? C21 C26 1.385(4) . ? C22 C23 1.380(5) . ? C22 H22 0.9300 . ? C23 C24 1.366(6) . ? C23 H23 0.9300 . ? C24 C25 1.377(6) . ? C24 H24 0.9300 . ? C25 C26 1.356(4) . ? C25 H25 0.9300 . ? C26 H26 0.9300 . ? C27 C32 1.379(3) . ? C27 C28 1.380(3) . ? C28 C29 1.373(3) . ? C28 H28 0.9300 . ? C29 C30 1.379(3) . ? C29 H29 0.9300 . ? C30 C31 1.381(3) . ? C30 C33 1.503(3) . ? C31 C32 1.374(3) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 C35 1.454(5) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 C36 1.450(7) . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 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 O3 S1 O4 119.62(10) . . ? O3 S1 N2 108.42(9) . . ? O4 S1 N2 103.18(9) . . ? O3 S1 C27 109.21(10) . . ? O4 S1 C27 108.75(9) . . ? N2 S1 C27 106.88(9) . . ? C1 N1 C8 110.50(19) . . ? C1 N1 H1 127.9(18) . . ? C8 N1 H1 120.6(18) . . ? C9 N2 C8 114.10(16) . . ? C9 N2 S1 123.61(14) . . ? C8 N2 S1 122.21(13) . . ? C11 N3 C12 126.86(18) . . ? C11 N3 C20 118.21(19) . . ? C12 N3 C20 114.28(19) . . ? N1 C1 C2 128.4(2) . . ? N1 C1 C6 110.38(19) . . ? C2 C1 C6 121.2(2) . . ? C3 C2 C1 118.1(2) . . ? C3 C2 H2 120.9 . . ? C1 C2 H2 120.9 . . ? C2 C3 C4 121.2(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 120.8(2) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 118.5(2) . . ? C6 C5 H5 120.8 . . ? C4 C5 H5 120.8 . . ? C5 C6 C1 120.1(2) . . ? C5 C6 C7 131.1(2) . . ? C1 C6 C7 108.37(18) . . ? C13 C7 C6 110.71(16) . . ? C13 C7 C10 111.05(16) . . ? C6 C7 C10 116.57(17) . . ? C13 C7 C8 112.62(17) . . ? C6 C7 C8 100.69(16) . . ? C10 C7 C8 104.65(15) . . ? N1 C8 N2 113.87(17) . . ? N1 C8 C7 104.90(17) . . ? N2 C8 C7 101.95(15) . . ? N1 C8 H8 111.8 . . ? N2 C8 H8 111.8 . . ? C7 C8 H8 111.8 . . ? O1 C9 N2 124.28(19) . . ? O1 C9 C10 129.75(19) . . ? N2 C9 C10 105.93(16) . . ? C14 C10 C9 114.88(17) . . ? C14 C10 C7 115.13(16) . . ? C9 C10 C7 102.47(15) . . ? C14 C10 C11 108.96(16) . . ? C9 C10 C11 102.42(16) . . ? C7 C10 C11 112.24(17) . . ? O2 C11 N3 123.1(2) . . ? O2 C11 C10 117.8(2) . . ? N3 C11 C10 119.12(18) . . ? N3 C12 C13 113.51(19) . . ? N3 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? N3 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C12 C13 C7 112.27(18) . . ? C12 C13 H13A 109.2 . . ? C7 C13 H13A 109.2 . . ? C12 C13 H13B 109.2 . . ? C7 C13 H13B 109.2 . . ? H13A C13 H13B 107.9 . . ? C19 C14 C15 118.0(2) . . ? C19 C14 C10 122.8(2) . . ? C15 C14 C10 119.2(2) . . ? C16 C15 C14 120.6(3) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C17 C16 C15 120.7(3) . . ? C17 C16 H16 119.7 . . ? C15 C16 H16 119.7 . . ? C16 C17 C18 119.8(3) . . ? C16 C17 H17 120.1 . . ? C18 C17 H17 120.1 . . ? C17 C18 C19 119.8(3) . . ? C17 C18 H18 120.1 . . ? C19 C18 H18 120.1 . . ? C14 C19 C18 121.1(3) . . ? C14 C19 H19 119.4 . . ? C18 C19 H19 119.4 . . ? N3 C20 C21 111.20(19) . . ? N3 C20 H20A 109.4 . . ? C21 C20 H20A 109.4 . . ? N3 C20 H20B 109.4 . . ? C21 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? C22 C21 C26 118.7(3) . . ? C22 C21 C20 120.6(3) . . ? C26 C21 C20 120.6(2) . . ? C21 C22 C23 120.2(3) . . ? C21 C22 H22 119.9 . . ? C23 C22 H22 119.9 . . ? C24 C23 C22 119.9(4) . . ? C24 C23 H23 120.1 . . ? C22 C23 H23 120.1 . . ? C23 C24 C25 120.3(4) . . ? C23 C24 H24 119.8 . . ? C25 C24 H24 119.8 . . ? C26 C25 C24 119.6(4) . . ? C26 C25 H25 120.2 . . ? C24 C25 H25 120.2 . . ? C25 C26 C21 121.2(3) . . ? C25 C26 H26 119.4 . . ? C21 C26 H26 119.4 . . ? C32 C27 C28 120.5(2) . . ? C32 C27 S1 119.37(16) . . ? C28 C27 S1 120.16(17) . . ? C29 C28 C27 119.2(2) . . ? C29 C28 H28 120.4 . . ? C27 C28 H28 120.4 . . ? C28 C29 C30 121.6(2) . . ? C28 C29 H29 119.2 . . ? C30 C29 H29 119.2 . . ? C29 C30 C31 117.9(2) . . ? C29 C30 C33 121.8(2) . . ? C31 C30 C33 120.3(2) . . ? C32 C31 C30 121.8(2) . . ? C32 C31 H31 119.1 . . ? C30 C31 H31 119.1 . . ? C31 C32 C27 119.0(2) . . ? C31 C32 H32 120.5 . . ? C27 C32 H32 120.5 . . ? C30 C33 H33A 109.5 . . ? C30 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C30 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C35 C34 H34A 109.5 . . ? C35 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C35 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? O5 C35 C36 121.8(5) . . ? O5 C35 C34 118.2(4) . . ? C36 C35 C34 120.0(4) . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 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 O3 S1 N2 C9 40.06(19) . . . . ? O4 S1 N2 C9 167.86(16) . . . . ? C27 S1 N2 C9 -77.55(18) . . . . ? O3 S1 N2 C8 -136.52(16) . . . . ? O4 S1 N2 C8 -8.72(17) . . . . ? C27 S1 N2 C8 105.87(16) . . . . ? C8 N1 C1 C2 168.7(2) . . . . ? C8 N1 C1 C6 -14.3(3) . . . . ? N1 C1 C2 C3 176.0(2) . . . . ? C6 C1 C2 C3 -0.7(3) . . . . ? C1 C2 C3 C4 -1.6(4) . . . . ? C2 C3 C4 C5 1.2(4) . . . . ? C3 C4 C5 C6 1.4(4) . . . . ? C4 C5 C6 C1 -3.6(3) . . . . ? C4 C5 C6 C7 -175.0(2) . . . . ? N1 C1 C6 C5 -173.9(2) . . . . ? C2 C1 C6 C5 3.3(3) . . . . ? N1 C1 C6 C7 -0.8(2) . . . . ? C2 C1 C6 C7 176.47(19) . . . . ? C5 C6 C7 C13 66.3(3) . . . . ? C1 C6 C7 C13 -105.8(2) . . . . ? C5 C6 C7 C10 -61.9(3) . . . . ? C1 C6 C7 C10 125.99(19) . . . . ? C5 C6 C7 C8 -174.4(2) . . . . ? C1 C6 C7 C8 13.5(2) . . . . ? C1 N1 C8 N2 -88.0(2) . . . . ? C1 N1 C8 C7 22.6(2) . . . . ? C9 N2 C8 N1 117.5(2) . . . . ? S1 N2 C8 N1 -65.6(2) . . . . ? C9 N2 C8 C7 5.1(2) . . . . ? S1 N2 C8 C7 -178.02(13) . . . . ? C13 C7 C8 N1 96.8(2) . . . . ? C6 C7 C8 N1 -21.1(2) . . . . ? C10 C7 C8 N1 -142.44(17) . . . . ? C13 C7 C8 N2 -144.21(16) . . . . ? C6 C7 C8 N2 97.85(17) . . . . ? C10 C7 C8 N2 -23.48(19) . . . . ? C8 N2 C9 O1 -166.3(2) . . . . ? S1 N2 C9 O1 16.9(3) . . . . ? C8 N2 C9 C10 15.8(2) . . . . ? S1 N2 C9 C10 -161.04(14) . . . . ? O1 C9 C10 C14 26.9(3) . . . . ? N2 C9 C10 C14 -155.28(16) . . . . ? O1 C9 C10 C7 152.5(2) . . . . ? N2 C9 C10 C7 -29.7(2) . . . . ? O1 C9 C10 C11 -91.0(3) . . . . ? N2 C9 C10 C11 86.76(18) . . . . ? C13 C7 C10 C14 -80.2(2) . . . . ? C6 C7 C10 C14 47.8(2) . . . . ? C8 C7 C10 C14 158.03(17) . . . . ? C13 C7 C10 C9 154.37(17) . . . . ? C6 C7 C10 C9 -77.6(2) . . . . ? C8 C7 C10 C9 32.6(2) . . . . ? C13 C7 C10 C11 45.2(2) . . . . ? C6 C7 C10 C11 173.24(17) . . . . ? C8 C7 C10 C11 -76.56(19) . . . . ? C12 N3 C11 O2 -177.9(2) . . . . ? C20 N3 C11 O2 -7.7(3) . . . . ? C12 N3 C11 C10 1.7(3) . . . . ? C20 N3 C11 C10 171.89(19) . . . . ? C14 C10 C11 O2 -69.7(2) . . . . ? C9 C10 C11 O2 52.4(2) . . . . ? C7 C10 C11 O2 161.62(19) . . . . ? C14 C10 C11 N3 110.8(2) . . . . ? C9 C10 C11 N3 -127.1(2) . . . . ? C7 C10 C11 N3 -18.0(3) . . . . ? C11 N3 C12 C13 -13.2(3) . . . . ? C20 N3 C12 C13 176.3(2) . . . . ? N3 C12 C13 C7 41.1(3) . . . . ? C6 C7 C13 C12 170.95(19) . . . . ? C10 C7 C13 C12 -57.9(2) . . . . ? C8 C7 C13 C12 59.1(2) . . . . ? C9 C10 C14 C19 25.0(3) . . . . ? C7 C10 C14 C19 -93.7(2) . . . . ? C11 C10 C14 C19 139.2(2) . . . . ? C9 C10 C14 C15 -157.12(19) . . . . ? C7 C10 C14 C15 84.2(2) . . . . ? C11 C10 C14 C15 -42.9(3) . . . . ? C19 C14 C15 C16 2.3(4) . . . . ? C10 C14 C15 C16 -175.6(2) . . . . ? C14 C15 C16 C17 -1.5(4) . . . . ? C15 C16 C17 C18 -0.4(5) . . . . ? C16 C17 C18 C19 1.4(5) . . . . ? C15 C14 C19 C18 -1.3(3) . . . . ? C10 C14 C19 C18 176.5(2) . . . . ? C17 C18 C19 C14 -0.5(4) . . . . ? C11 N3 C20 C21 -104.7(2) . . . . ? C12 N3 C20 C21 66.7(3) . . . . ? N3 C20 C21 C22 -128.6(2) . . . . ? N3 C20 C21 C26 51.5(3) . . . . ? C26 C21 C22 C23 -0.1(4) . . . . ? C20 C21 C22 C23 180.0(3) . . . . ? C21 C22 C23 C24 -0.4(5) . . . . ? C22 C23 C24 C25 0.6(5) . . . . ? C23 C24 C25 C26 -0.2(5) . . . . ? C24 C25 C26 C21 -0.4(5) . . . . ? C22 C21 C26 C25 0.5(4) . . . . ? C20 C21 C26 C25 -179.6(2) . . . . ? O3 S1 C27 C32 159.53(18) . . . . ? O4 S1 C27 C32 27.4(2) . . . . ? N2 S1 C27 C32 -83.37(19) . . . . ? O3 S1 C27 C28 -19.2(2) . . . . ? O4 S1 C27 C28 -151.31(18) . . . . ? N2 S1 C27 C28 97.92(19) . . . . ? C32 C27 C28 C29 0.3(4) . . . . ? S1 C27 C28 C29 178.98(19) . . . . ? C27 C28 C29 C30 0.3(4) . . . . ? C28 C29 C30 C31 -0.6(4) . . . . ? C28 C29 C30 C33 179.1(2) . . . . ? C29 C30 C31 C32 0.4(4) . . . . ? C33 C30 C31 C32 -179.4(2) . . . . ? C30 C31 C32 C27 0.2(4) . . . . ? C28 C27 C32 C31 -0.5(3) . . . . ? S1 C27 C32 C31 -179.24(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1 O4 0.81(3) 2.20(3) 2.975(3) 163(2) 3_665 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.331 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.042