# 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_email liyj@iccas.ac.cn _publ_contact_author_name 'Yuliang Li' loop_ _publ_author_name 'Songhua Chen' 'Nan Chen' 'Yongli Yan' 'Taifeng Liu' 'Yanwen Yu' ; Yongjun Li ; 'Huibiao Liu' 'Yong Sheng Zhao' 'Yuliang Li' data_a _database_code_depnum_ccdc_archive 'CCDC 859087' #TrackingRef 'web_deposit_cif_file_0_SonghuaChen_1324090378.BTN-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H20 N4 O2 S' _chemical_formula_sum 'C34 H20 N4 O2 S' _chemical_formula_weight 548.60 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 10.064(2) _cell_length_b 8.9812(18) _cell_length_c 28.804(6) _cell_angle_alpha 90.00 _cell_angle_beta 97.80(3) _cell_angle_gamma 90.00 _cell_volume 2579.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3923 _cell_measurement_theta_min 2.2677 _cell_measurement_theta_max 26.3585 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1136 _exptl_absorpt_coefficient_mu 0.167 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3515 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating Anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007HF + CCD (Saturn724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean 28.5714 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9997 _diffrn_reflns_av_R_equivalents 0.0748 _diffrn_reflns_av_sigmaI/netI 0.0904 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4514 _reflns_number_gt 3482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2008)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2008)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; Mercury: visualization and analysis of crystal structures, C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006. ; _computing_publication_material 'SHELX-97 (Sheldrick, 1997)' _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^)+(0.0348P)^2^+5.4913P] 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 4514 _refine_ls_number_parameters 370 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1291 _refine_ls_R_factor_gt 0.0991 _refine_ls_wR_factor_ref 0.1908 _refine_ls_wR_factor_gt 0.1746 _refine_ls_goodness_of_fit_ref 1.143 _refine_ls_restrained_S_all 1.143 _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 0.98374(11) 2.15584(13) 0.54531(5) 0.0389(3) Uani 1 1 d . . . C16 C 0.6826(4) 0.8337(4) 0.39595(16) 0.0273(10) Uani 1 1 d . . . C34 C 0.8190(4) 1.9954(4) 0.56896(16) 0.0278(10) Uani 1 1 d . . . C21 C 0.7432(4) 1.2285(4) 0.44846(17) 0.0290(10) Uani 1 1 d . . . N1 N 0.7084(3) 0.4249(4) 0.32536(14) 0.0318(9) Uani 1 1 d . . . C28 C 0.7391(4) 1.7399(5) 0.54890(17) 0.0301(11) Uani 1 1 d . . . C12 C 0.6027(4) 0.3355(4) 0.30503(16) 0.0281(10) Uani 1 1 d . . . C32 C 0.7195(4) 2.1414(5) 0.62658(17) 0.0319(11) Uani 1 1 d . . . C17 C 0.7606(4) 0.8196(5) 0.35932(17) 0.0338(11) Uani 1 1 d . . . H17 H 0.8096 0.9031 0.3506 0.041 Uiso 1 1 calc R . . C13 C 0.6964(4) 0.5638(4) 0.34787(16) 0.0279(10) Uani 1 1 d . . . C15 C 0.6080(4) 0.7097(5) 0.40610(17) 0.0315(11) Uani 1 1 d . . . H15 H 0.5508 0.7178 0.4296 0.038 Uiso 1 1 calc R . . N2 N 0.9123(3) 1.9950(4) 0.53956(14) 0.0326(9) Uani 1 1 d . . . O2 O 0.6471(4) 2.2699(4) 0.68778(14) 0.0527(10) Uani 1 1 d . . . C20 C 0.7464(4) 1.0935(5) 0.42015(17) 0.0314(11) Uani 1 1 d . . . H20 H 0.8040 1.0953 0.3966 0.038 Uiso 1 1 calc R . . C26 C 0.8400(4) 1.3381(5) 0.44549(17) 0.0310(11) Uani 1 1 d . . . H26 H 0.9064 1.3224 0.4255 0.037 Uiso 1 1 calc R . . C19 C 0.6777(4) 0.9692(5) 0.42369(17) 0.0315(11) Uani 1 1 d . . . H19 H 0.6188 0.9681 0.4468 0.038 Uiso 1 1 calc R . . N3 N 0.9050(4) 2.2324(4) 0.58419(15) 0.0364(10) Uani 1 1 d . . . C24 C 0.7469(4) 1.4919(4) 0.50075(17) 0.0309(11) Uani 1 1 d . . . N4 N 0.7043(4) 2.2785(5) 0.65276(17) 0.0424(11) Uani 1 1 d . . . C14 C 0.6147(4) 0.5759(5) 0.38313(17) 0.0301(11) Uani 1 1 d . . . H14 H 0.5642 0.4928 0.3912 0.036 Uiso 1 1 calc R . . C30 C 0.6443(4) 1.8904(5) 0.60752(17) 0.0338(11) Uani 1 1 d . . . H30 H 0.5853 1.8112 0.6125 0.041 Uiso 1 1 calc R . . C25 C 0.8419(4) 1.4679(5) 0.47067(17) 0.0324(11) Uani 1 1 d . . . H25 H 0.9080 1.5414 0.4676 0.039 Uiso 1 1 calc R . . O1 O 0.7443(4) 2.3951(4) 0.63751(16) 0.0642(12) Uani 1 1 d . . . C27 C 0.7455(4) 1.6277(5) 0.52677(17) 0.0328(11) Uani 1 1 d . . . C29 C 0.7327(4) 1.8734(4) 0.57537(17) 0.0298(10) Uani 1 1 d . . . C23 C 0.6509(4) 1.3830(5) 0.50450(18) 0.0358(12) Uani 1 1 d . . . H23 H 0.5859 1.3982 0.5250 0.043 Uiso 1 1 calc R . . C1 C 0.8290(4) 0.3504(5) 0.32196(17) 0.0309(11) Uani 1 1 d . . . C4 C 1.0346(5) 0.1622(5) 0.30748(19) 0.0418(13) Uani 1 1 d . . . H4 H 1.1068 0.0987 0.3025 0.050 Uiso 1 1 calc R . . C22 C 0.6484(4) 1.2533(5) 0.47895(19) 0.0366(12) Uani 1 1 d . . . H22 H 0.5820 1.1802 0.4820 0.044 Uiso 1 1 calc R . . C6 C 0.7993(4) 0.2124(5) 0.30044(16) 0.0281(10) Uani 1 1 d . . . C18 C 0.7672(4) 0.6870(5) 0.33578(17) 0.0328(11) Uani 1 1 d . . . H18 H 0.8206 0.6799 0.3111 0.039 Uiso 1 1 calc R . . C33 C 0.8142(4) 2.1315(5) 0.59421(17) 0.0305(11) Uani 1 1 d . . . C31 C 0.6402(4) 2.0236(5) 0.63314(17) 0.0352(11) Uani 1 1 d . . . H31 H 0.5799 2.0309 0.6557 0.042 Uiso 1 1 calc R . . C7 C 0.6543(4) 0.2011(5) 0.28976(17) 0.0310(10) Uani 1 1 d . . . C2 C 0.9603(4) 0.3946(5) 0.33764(17) 0.0323(11) Uani 1 1 d . . . H2 H 0.9790 0.4871 0.3531 0.039 Uiso 1 1 calc R . . C11 C 0.4657(4) 0.3653(5) 0.29775(17) 0.0344(11) Uani 1 1 d . . . H11 H 0.4308 0.4558 0.3082 0.041 Uiso 1 1 calc R . . C3 C 1.0615(4) 0.2987(5) 0.32978(18) 0.0377(12) Uani 1 1 d . . . H3 H 1.1520 0.3263 0.3398 0.045 Uiso 1 1 calc R . . C8 C 0.5684(5) 0.0940(5) 0.26817(17) 0.0350(11) Uani 1 1 d . . . H8 H 0.6021 0.0016 0.2587 0.042 Uiso 1 1 calc R . . C10 C 0.3826(5) 0.2592(5) 0.27501(18) 0.0404(12) Uani 1 1 d . . . H10 H 0.2890 0.2782 0.2689 0.048 Uiso 1 1 calc R . . C9 C 0.4323(5) 0.1243(5) 0.26066(18) 0.0395(12) Uani 1 1 d . . . H9 H 0.3721 0.0524 0.2456 0.047 Uiso 1 1 calc R . . C5 C 0.9047(4) 0.1181(5) 0.29250(18) 0.0373(12) Uani 1 1 d . . . H5 H 0.8870 0.0253 0.2771 0.045 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 0.0351(6) 0.0333(6) 0.0488(9) -0.0002(6) 0.0082(6) -0.0034(5) C16 0.027(2) 0.028(2) 0.027(3) -0.0016(19) 0.0012(19) 0.0033(18) C34 0.025(2) 0.025(2) 0.032(3) -0.0040(19) -0.0001(19) 0.0018(17) C21 0.031(2) 0.025(2) 0.030(3) 0.0028(19) -0.0011(19) -0.0002(18) N1 0.0315(19) 0.0230(18) 0.041(3) -0.0079(17) 0.0046(17) -0.0002(15) C28 0.029(2) 0.025(2) 0.036(3) -0.001(2) 0.006(2) -0.0031(18) C12 0.031(2) 0.022(2) 0.032(3) -0.0024(19) 0.0064(19) -0.0031(18) C32 0.032(2) 0.029(2) 0.033(3) -0.006(2) -0.002(2) 0.0030(19) C17 0.037(2) 0.029(2) 0.037(3) 0.000(2) 0.012(2) -0.008(2) C13 0.027(2) 0.027(2) 0.028(3) -0.0029(19) 0.0003(19) -0.0006(18) C15 0.027(2) 0.034(2) 0.034(3) -0.004(2) 0.0043(19) -0.0007(19) N2 0.0321(19) 0.033(2) 0.034(3) 0.0007(18) 0.0087(18) 0.0023(16) O2 0.058(2) 0.060(2) 0.041(3) -0.017(2) 0.0092(19) 0.0157(19) C20 0.032(2) 0.033(2) 0.029(3) -0.003(2) 0.004(2) 0.0001(19) C26 0.030(2) 0.032(2) 0.031(3) 0.001(2) 0.0063(19) 0.0006(19) C19 0.031(2) 0.031(2) 0.032(3) -0.006(2) 0.003(2) 0.0028(19) N3 0.034(2) 0.0305(19) 0.044(3) -0.0049(18) 0.0028(18) 0.0000(17) C24 0.037(2) 0.023(2) 0.033(3) 0.000(2) 0.005(2) -0.0006(18) N4 0.037(2) 0.042(2) 0.046(3) -0.014(2) -0.003(2) 0.0086(19) C14 0.025(2) 0.027(2) 0.038(3) 0.002(2) 0.002(2) -0.0027(18) C30 0.035(2) 0.033(2) 0.033(3) 0.001(2) 0.003(2) -0.0024(19) C25 0.031(2) 0.029(2) 0.037(3) 0.003(2) 0.004(2) -0.0025(19) O1 0.071(3) 0.034(2) 0.092(4) -0.022(2) 0.028(2) -0.0040(19) C27 0.033(2) 0.029(2) 0.035(3) 0.001(2) 0.000(2) -0.0008(19) C29 0.032(2) 0.027(2) 0.031(3) 0.000(2) 0.003(2) 0.0026(18) C23 0.040(3) 0.028(2) 0.041(3) -0.002(2) 0.012(2) -0.002(2) C1 0.030(2) 0.029(2) 0.036(3) 0.002(2) 0.013(2) 0.0037(19) C4 0.035(2) 0.037(3) 0.056(4) 0.006(3) 0.015(2) 0.010(2) C22 0.033(2) 0.028(2) 0.051(4) -0.005(2) 0.014(2) -0.0055(19) C6 0.033(2) 0.029(2) 0.025(3) 0.004(2) 0.0133(19) -0.0003(19) C18 0.038(2) 0.029(2) 0.032(3) -0.003(2) 0.010(2) -0.002(2) C33 0.026(2) 0.031(2) 0.033(3) -0.003(2) 0.0008(19) -0.0030(19) C31 0.028(2) 0.044(3) 0.032(3) -0.002(2) 0.003(2) 0.005(2) C7 0.037(2) 0.028(2) 0.029(3) 0.001(2) 0.010(2) 0.0006(19) C2 0.034(2) 0.033(2) 0.030(3) 0.000(2) 0.004(2) -0.0006(19) C11 0.036(2) 0.033(2) 0.035(3) -0.002(2) 0.009(2) 0.002(2) C3 0.024(2) 0.044(3) 0.045(4) 0.005(2) 0.004(2) 0.004(2) C8 0.047(3) 0.031(2) 0.030(3) -0.007(2) 0.015(2) -0.002(2) C10 0.033(2) 0.045(3) 0.043(4) 0.000(2) 0.005(2) -0.005(2) C9 0.042(3) 0.036(3) 0.041(3) -0.005(2) 0.009(2) -0.011(2) C5 0.041(3) 0.031(2) 0.043(3) 0.001(2) 0.017(2) 0.003(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 N3 1.611(4) . ? S1 N2 1.612(4) . ? C16 C15 1.396(6) . ? C16 C17 1.404(6) . ? C16 C19 1.461(6) . ? C34 N2 1.347(6) . ? C34 C29 1.425(6) . ? C34 C33 1.427(6) . ? C21 C26 1.396(6) . ? C21 C22 1.399(6) . ? C21 C20 1.464(6) . ? N1 C12 1.396(5) . ? N1 C1 1.401(5) . ? N1 C13 1.419(5) . ? C28 C27 1.198(6) . ? C28 C29 1.428(6) . ? C12 C11 1.393(6) . ? C12 C7 1.408(6) . ? C32 C31 1.354(6) . ? C32 C33 1.423(6) . ? C32 N4 1.463(6) . ? C17 C18 1.377(6) . ? C17 H17 0.9500 . ? C13 C18 1.386(6) . ? C13 C14 1.395(6) . ? C15 C14 1.378(6) . ? C15 H15 0.9500 . ? O2 N4 1.230(5) . ? C20 C19 1.324(6) . ? C20 H20 0.9500 . ? C26 C25 1.371(6) . ? C26 H26 0.9500 . ? C19 H19 0.9500 . ? N3 C33 1.346(5) . ? C24 C23 1.389(6) . ? C24 C25 1.392(6) . ? C24 C27 1.432(6) . ? N4 O1 1.224(5) . ? C14 H14 0.9500 . ? C30 C29 1.377(6) . ? C30 C31 1.409(6) . ? C30 H30 0.9500 . ? C25 H25 0.9500 . ? C23 C22 1.376(6) . ? C23 H23 0.9500 . ? C1 C2 1.394(6) . ? C1 C6 1.399(6) . ? C4 C5 1.378(6) . ? C4 C3 1.393(7) . ? C4 H4 0.9500 . ? C22 H22 0.9500 . ? C6 C5 1.401(6) . ? C6 C7 1.453(6) . ? C18 H18 0.9500 . ? C31 H31 0.9500 . ? C7 C8 1.383(6) . ? C2 C3 1.376(6) . ? C2 H2 0.9500 . ? C11 C10 1.373(6) . ? C11 H11 0.9500 . ? C3 H3 0.9500 . ? C8 C9 1.385(6) . ? C8 H8 0.9500 . ? C10 C9 1.395(6) . ? C10 H10 0.9500 . ? C9 H9 0.9500 . ? C5 H5 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 N3 S1 N2 101.5(2) . . ? C15 C16 C17 117.2(4) . . ? C15 C16 C19 119.4(4) . . ? C17 C16 C19 123.4(4) . . ? N2 C34 C29 124.6(4) . . ? N2 C34 C33 113.4(4) . . ? C29 C34 C33 121.9(4) . . ? C26 C21 C22 117.9(4) . . ? C26 C21 C20 118.8(4) . . ? C22 C21 C20 123.3(4) . . ? C12 N1 C1 108.3(3) . . ? C12 N1 C13 126.1(3) . . ? C1 N1 C13 125.5(4) . . ? C27 C28 C29 179.5(5) . . ? C11 C12 N1 129.4(4) . . ? C11 C12 C7 121.2(4) . . ? N1 C12 C7 109.4(3) . . ? C31 C32 C33 120.2(4) . . ? C31 C32 N4 118.8(4) . . ? C33 C32 N4 121.1(4) . . ? C18 C17 C16 121.2(4) . . ? C18 C17 H17 119.4 . . ? C16 C17 H17 119.4 . . ? C18 C13 C14 119.7(4) . . ? C18 C13 N1 120.6(4) . . ? C14 C13 N1 119.8(4) . . ? C14 C15 C16 122.2(4) . . ? C14 C15 H15 118.9 . . ? C16 C15 H15 118.9 . . ? C34 N2 S1 105.8(3) . . ? C19 C20 C21 127.2(4) . . ? C19 C20 H20 116.4 . . ? C21 C20 H20 116.4 . . ? C25 C26 C21 121.7(4) . . ? C25 C26 H26 119.1 . . ? C21 C26 H26 119.1 . . ? C20 C19 C16 127.2(4) . . ? C20 C19 H19 116.4 . . ? C16 C19 H19 116.4 . . ? C33 N3 S1 105.9(3) . . ? C23 C24 C25 118.9(4) . . ? C23 C24 C27 120.2(4) . . ? C25 C24 C27 120.9(4) . . ? O1 N4 O2 124.2(4) . . ? O1 N4 C32 118.2(5) . . ? O2 N4 C32 117.6(4) . . ? C15 C14 C13 119.3(4) . . ? C15 C14 H14 120.3 . . ? C13 C14 H14 120.3 . . ? C29 C30 C31 120.9(4) . . ? C29 C30 H30 119.5 . . ? C31 C30 H30 119.5 . . ? C26 C25 C24 120.0(4) . . ? C26 C25 H25 120.0 . . ? C24 C25 H25 120.0 . . ? C28 C27 C24 177.3(5) . . ? C30 C29 C34 117.6(4) . . ? C30 C29 C28 122.1(4) . . ? C34 C29 C28 120.3(4) . . ? C22 C23 C24 121.1(4) . . ? C22 C23 H23 119.4 . . ? C24 C23 H23 119.4 . . ? C2 C1 C6 122.1(4) . . ? C2 C1 N1 129.3(4) . . ? C6 C1 N1 108.6(4) . . ? C5 C4 C3 121.0(4) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C23 C22 C21 120.4(4) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C1 C6 C5 119.1(4) . . ? C1 C6 C7 107.7(4) . . ? C5 C6 C7 133.1(4) . . ? C17 C18 C13 120.4(4) . . ? C17 C18 H18 119.8 . . ? C13 C18 H18 119.8 . . ? N3 C33 C32 129.3(4) . . ? N3 C33 C34 113.3(4) . . ? C32 C33 C34 117.3(4) . . ? C32 C31 C30 122.0(5) . . ? C32 C31 H31 119.0 . . ? C30 C31 H31 119.0 . . ? C8 C7 C12 120.1(4) . . ? C8 C7 C6 133.8(4) . . ? C12 C7 C6 106.0(4) . . ? C3 C2 C1 117.3(4) . . ? C3 C2 H2 121.3 . . ? C1 C2 H2 121.3 . . ? C10 C11 C12 117.7(4) . . ? C10 C11 H11 121.2 . . ? C12 C11 H11 121.2 . . ? C2 C3 C4 121.6(4) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C7 C8 C9 118.6(4) . . ? C7 C8 H8 120.7 . . ? C9 C8 H8 120.7 . . ? C11 C10 C9 121.6(4) . . ? C11 C10 H10 119.2 . . ? C9 C10 H10 119.2 . . ? C8 C9 C10 120.8(4) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C4 C5 C6 118.8(4) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? 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 C1 N1 C12 C11 -176.0(5) . . . . ? C13 N1 C12 C11 7.0(8) . . . . ? C1 N1 C12 C7 1.8(5) . . . . ? C13 N1 C12 C7 -175.1(4) . . . . ? C15 C16 C17 C18 -2.6(6) . . . . ? C19 C16 C17 C18 176.6(4) . . . . ? C12 N1 C13 C18 -129.5(5) . . . . ? C1 N1 C13 C18 54.1(6) . . . . ? C12 N1 C13 C14 51.8(6) . . . . ? C1 N1 C13 C14 -124.6(5) . . . . ? C17 C16 C15 C14 3.2(6) . . . . ? C19 C16 C15 C14 -176.0(4) . . . . ? C29 C34 N2 S1 -179.4(4) . . . . ? C33 C34 N2 S1 0.1(5) . . . . ? N3 S1 N2 C34 0.5(3) . . . . ? C26 C21 C20 C19 168.5(5) . . . . ? C22 C21 C20 C19 -10.9(7) . . . . ? C22 C21 C26 C25 -1.3(7) . . . . ? C20 C21 C26 C25 179.3(4) . . . . ? C21 C20 C19 C16 -178.9(4) . . . . ? C15 C16 C19 C20 176.7(4) . . . . ? C17 C16 C19 C20 -2.5(7) . . . . ? N2 S1 N3 C33 -0.9(3) . . . . ? C31 C32 N4 O1 -158.7(4) . . . . ? C33 C32 N4 O1 20.4(6) . . . . ? C31 C32 N4 O2 18.5(6) . . . . ? C33 C32 N4 O2 -162.4(4) . . . . ? C16 C15 C14 C13 -1.3(7) . . . . ? C18 C13 C14 C15 -1.4(6) . . . . ? N1 C13 C14 C15 177.3(4) . . . . ? C21 C26 C25 C24 1.1(7) . . . . ? C23 C24 C25 C26 -0.3(7) . . . . ? C27 C24 C25 C26 -178.9(4) . . . . ? C29 C28 C27 C24 152(100) . . . . ? C23 C24 C27 C28 -14(11) . . . . ? C25 C24 C27 C28 164(11) . . . . ? C31 C30 C29 C34 -0.2(7) . . . . ? C31 C30 C29 C28 -180.0(4) . . . . ? N2 C34 C29 C30 178.7(4) . . . . ? C33 C34 C29 C30 -0.7(6) . . . . ? N2 C34 C29 C28 -1.5(7) . . . . ? C33 C34 C29 C28 179.0(4) . . . . ? C27 C28 C29 C30 -132(100) . . . . ? C27 C28 C29 C34 49(54) . . . . ? C25 C24 C23 C22 -0.3(7) . . . . ? C27 C24 C23 C22 178.4(4) . . . . ? C12 N1 C1 C2 -179.3(5) . . . . ? C13 N1 C1 C2 -2.3(8) . . . . ? C12 N1 C1 C6 -1.3(5) . . . . ? C13 N1 C1 C6 175.6(4) . . . . ? C24 C23 C22 C21 0.0(7) . . . . ? C26 C21 C22 C23 0.8(7) . . . . ? C20 C21 C22 C23 -179.9(4) . . . . ? C2 C1 C6 C5 -2.8(7) . . . . ? N1 C1 C6 C5 179.0(4) . . . . ? C2 C1 C6 C7 178.5(4) . . . . ? N1 C1 C6 C7 0.4(5) . . . . ? C16 C17 C18 C13 0.1(7) . . . . ? C14 C13 C18 C17 2.0(7) . . . . ? N1 C13 C18 C17 -176.7(4) . . . . ? S1 N3 C33 C32 179.3(4) . . . . ? S1 N3 C33 C34 1.1(5) . . . . ? C31 C32 C33 N3 -176.9(5) . . . . ? N4 C32 C33 N3 4.0(7) . . . . ? C31 C32 C33 C34 1.2(6) . . . . ? N4 C32 C33 C34 -177.8(4) . . . . ? N2 C34 C33 N3 -0.8(6) . . . . ? C29 C34 C33 N3 178.7(4) . . . . ? N2 C34 C33 C32 -179.3(4) . . . . ? C29 C34 C33 C32 0.3(6) . . . . ? C33 C32 C31 C30 -2.3(7) . . . . ? N4 C32 C31 C30 176.8(4) . . . . ? C29 C30 C31 C32 1.8(7) . . . . ? C11 C12 C7 C8 -1.7(7) . . . . ? N1 C12 C7 C8 -179.8(4) . . . . ? C11 C12 C7 C6 176.5(4) . . . . ? N1 C12 C7 C6 -1.6(5) . . . . ? C1 C6 C7 C8 178.6(5) . . . . ? C5 C6 C7 C8 0.1(9) . . . . ? C1 C6 C7 C12 0.7(5) . . . . ? C5 C6 C7 C12 -177.7(5) . . . . ? C6 C1 C2 C3 2.1(7) . . . . ? N1 C1 C2 C3 179.8(5) . . . . ? N1 C12 C11 C10 177.4(5) . . . . ? C7 C12 C11 C10 -0.2(7) . . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? C5 C4 C3 C2 -0.1(8) . . . . ? C12 C7 C8 C9 2.1(7) . . . . ? C6 C7 C8 C9 -175.5(5) . . . . ? C12 C11 C10 C9 1.7(8) . . . . ? C7 C8 C9 C10 -0.7(7) . . . . ? C11 C10 C9 C8 -1.2(8) . . . . ? C3 C4 C5 C6 -0.6(8) . . . . ? C1 C6 C5 C4 2.0(7) . . . . ? C7 C6 C5 C4 -179.7(5) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.298 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.067 # Attachment 'web_deposit_cif_file_1_SonghuaChen_1324090378.BTN-7.cif' data_a2 _database_code_depnum_ccdc_archive 'CCDC 859088' #TrackingRef 'web_deposit_cif_file_1_SonghuaChen_1324090378.BTN-7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H21 N3 S' _chemical_formula_sum 'C34 H21 N3 S' _chemical_formula_weight 503.60 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 9.0702(18) _cell_length_b 39.586(8) _cell_length_c 7.4369(15) _cell_angle_alpha 90.00 _cell_angle_beta 106.217(3) _cell_angle_gamma 90.00 _cell_volume 2564.0(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 5932 _cell_measurement_theta_min 2.06 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1048 _exptl_absorpt_coefficient_mu 0.155 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9696 _exptl_absorpt_correction_T_max 0.9756 _exptl_absorpt_process_details 'CrystalClear (Rigaku Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator Confocal _diffrn_measurement_device_type 'MM007-HF CCD(Saturn 724+)' _diffrn_measurement_method '\w scans at fixed \c = 45\%' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16145 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0467 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -46 _diffrn_reflns_limit_k_max 47 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.03 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4503 _reflns_number_gt 3932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Inc., 2007)' _computing_cell_refinement 'CrystalClear (Rigaku Inc., 2007)' _computing_data_reduction 'CrystalClear (Rigaku Inc., 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Olex2 Ver 1.1' _computing_publication_material 'SHELX97 (Sheldrick, 2008)' _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^)+(0.0409P)^2^+2.0317P] 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 4503 _refine_ls_number_parameters 343 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0862 _refine_ls_R_factor_gt 0.0746 _refine_ls_wR_factor_ref 0.1501 _refine_ls_wR_factor_gt 0.1445 _refine_ls_goodness_of_fit_ref 1.199 _refine_ls_restrained_S_all 1.199 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.54497(12) 0.13731(2) 0.68034(13) 0.0560(3) Uani 1 1 d . . . N1 N 0.4943(3) 0.13518(7) 0.8703(4) 0.0468(7) Uani 1 1 d . . . N2 N 0.6012(3) 0.09907(7) 0.6620(4) 0.0455(7) Uani 1 1 d . . . N3 N 1.1267(2) -0.17763(6) -0.4518(3) 0.0283(5) Uani 1 1 d . . . C1 C 0.6168(3) 0.04812(8) 0.8592(4) 0.0371(7) Uani 1 1 d . . . C2 C 0.5929(3) 0.03703(8) 1.0231(4) 0.0402(7) Uani 1 1 d . . . H2 H 0.6169 0.0142 1.0578 0.048 Uiso 1 1 calc R . . C3 C 0.5343(4) 0.05753(8) 1.1455(4) 0.0401(7) Uani 1 1 d . . . H3 H 0.5219 0.0483 1.2583 0.048 Uiso 1 1 calc R . . C4 C 0.4964(4) 0.09035(8) 1.0997(4) 0.0408(8) Uani 1 1 d . . . H4 H 0.4543 0.1042 1.1775 0.049 Uiso 1 1 calc R . . C5 C 0.5212(3) 0.10325(7) 0.9339(4) 0.0343(7) Uani 1 1 d . . . C6 C 0.5825(3) 0.08253(8) 0.8145(4) 0.0366(7) Uani 1 1 d . . . C7 C 0.6731(4) 0.02615(8) 0.7395(5) 0.0439(8) Uani 1 1 d . . . C8 C 0.7156(4) 0.00632(8) 0.6440(5) 0.0448(8) Uani 1 1 d . . . C9 C 0.7641(3) -0.01772(8) 0.5270(4) 0.0409(8) Uani 1 1 d . . . C10 C 0.8233(4) -0.00688(9) 0.3841(5) 0.0484(9) Uani 1 1 d . . . H10 H 0.8338 0.0166 0.3655 0.058 Uiso 1 1 calc R . . C11 C 0.8674(4) -0.02979(9) 0.2680(4) 0.0470(8) Uani 1 1 d . . . H11 H 0.9076 -0.0218 0.1707 0.056 Uiso 1 1 calc R . . C12 C 0.8531(3) -0.06446(8) 0.2929(4) 0.0386(7) Uani 1 1 d . . . C13 C 0.7961(4) -0.07507(9) 0.4374(5) 0.0491(9) Uani 1 1 d . . . H13 H 0.7869 -0.0986 0.4576 0.059 Uiso 1 1 calc R . . C14 C 0.7521(4) -0.05223(9) 0.5534(5) 0.0501(9) Uani 1 1 d . . . H14 H 0.7134 -0.0602 0.6518 0.060 Uiso 1 1 calc R . . C15 C 0.8971(4) -0.08975(8) 0.1721(4) 0.0412(8) Uani 1 1 d . . . H15 H 0.8702 -0.1125 0.1878 0.049 Uiso 1 1 calc R . . C16 C 0.9696(3) -0.08411(8) 0.0448(4) 0.0406(8) Uani 1 1 d . . . H16 H 0.9997 -0.0614 0.0325 0.049 Uiso 1 1 calc R . . C17 C 1.0092(3) -0.10899(7) -0.0806(4) 0.0339(7) Uani 1 1 d . . . C18 C 1.0944(4) -0.09900(8) -0.1990(5) 0.0432(8) Uani 1 1 d . . . H18 H 1.1273 -0.0762 -0.1962 0.052 Uiso 1 1 calc R . . C19 C 1.1331(4) -0.12128(7) -0.3210(4) 0.0394(7) Uani 1 1 d . . . H19 H 1.1920 -0.1137 -0.4006 0.047 Uiso 1 1 calc R . . C20 C 1.0869(3) -0.15418(7) -0.3275(4) 0.0281(6) Uani 1 1 d . . . C21 C 0.9998(4) -0.16489(8) -0.2129(5) 0.0502(9) Uani 1 1 d . . . H21 H 0.9659 -0.1877 -0.2181 0.060 Uiso 1 1 calc R . . C22 C 0.9622(4) -0.14253(8) -0.0913(5) 0.0528(9) Uani 1 1 d . . . H22 H 0.9026 -0.1502 -0.0126 0.063 Uiso 1 1 calc R . . C23 C 1.0262(3) -0.19180(6) -0.6102(4) 0.0268(6) Uani 1 1 d . . . C24 C 0.8677(3) -0.18857(7) -0.6769(4) 0.0337(7) Uani 1 1 d . . . H24 H 0.8120 -0.1748 -0.6142 0.040 Uiso 1 1 calc R . . C25 C 0.7939(3) -0.20612(8) -0.8374(4) 0.0386(7) Uani 1 1 d . . . H25 H 0.6855 -0.2044 -0.8860 0.046 Uiso 1 1 calc R . . C26 C 0.8762(4) -0.22639(8) -0.9295(4) 0.0411(8) Uani 1 1 d . . . H26 H 0.8231 -0.2382 -1.0398 0.049 Uiso 1 1 calc R . . C27 C 1.0330(4) -0.22943(7) -0.8622(4) 0.0363(7) Uani 1 1 d . . . H27 H 1.0878 -0.2433 -0.9259 0.044 Uiso 1 1 calc R . . C28 C 1.1111(3) -0.21219(7) -0.7007(4) 0.0297(6) Uani 1 1 d . . . C29 C 1.2697(3) -0.20975(7) -0.5932(4) 0.0304(6) Uani 1 1 d . . . C30 C 1.4068(4) -0.22366(7) -0.6119(5) 0.0393(8) Uani 1 1 d . . . H30 H 1.4065 -0.2381 -0.7140 0.047 Uiso 1 1 calc R . . C31 C 1.5407(4) -0.21599(8) -0.4798(5) 0.0436(8) Uani 1 1 d . . . H31 H 1.6344 -0.2250 -0.4922 0.052 Uiso 1 1 calc R . . C32 C 1.5436(3) -0.19522(8) -0.3271(4) 0.0418(8) Uani 1 1 d . . . H32 H 1.6389 -0.1906 -0.2376 0.050 Uiso 1 1 calc R . . C33 C 1.4109(3) -0.18130(7) -0.3039(4) 0.0354(7) Uani 1 1 d . . . H33 H 1.4123 -0.1674 -0.1995 0.042 Uiso 1 1 calc R . . C34 C 1.2751(3) -0.18855(7) -0.4399(4) 0.0281(6) 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 S1 0.0800(7) 0.0433(5) 0.0515(6) 0.0070(4) 0.0294(5) 0.0057(5) N1 0.0598(18) 0.0361(15) 0.0484(17) 0.0006(13) 0.0213(14) 0.0098(13) N2 0.0573(18) 0.0462(16) 0.0381(15) -0.0029(13) 0.0218(13) 0.0022(13) N3 0.0291(12) 0.0321(13) 0.0253(12) -0.0049(10) 0.0102(10) 0.0026(10) C1 0.0316(16) 0.0368(17) 0.0418(18) -0.0104(14) 0.0083(14) 0.0021(13) C2 0.0430(18) 0.0350(17) 0.0431(19) -0.0009(14) 0.0128(15) 0.0009(14) C3 0.0469(19) 0.0353(17) 0.0403(18) 0.0064(14) 0.0155(15) 0.0002(14) C4 0.0453(18) 0.0466(19) 0.0367(17) -0.0042(15) 0.0216(15) 0.0023(15) C5 0.0366(16) 0.0300(15) 0.0367(17) -0.0068(13) 0.0108(13) 0.0048(12) C6 0.0336(16) 0.0404(17) 0.0353(17) -0.0085(14) 0.0086(13) 0.0022(13) C7 0.0398(18) 0.0446(19) 0.0460(19) -0.0164(16) 0.0098(15) 0.0056(15) C8 0.0389(18) 0.0480(19) 0.0437(19) -0.0156(16) 0.0056(15) 0.0072(15) C9 0.0345(17) 0.0475(19) 0.0377(17) -0.0168(15) 0.0050(14) 0.0098(14) C10 0.057(2) 0.0436(19) 0.0414(19) -0.0083(16) 0.0091(17) 0.0121(16) C11 0.057(2) 0.051(2) 0.0347(18) -0.0047(16) 0.0158(16) 0.0093(16) C12 0.0330(16) 0.0408(18) 0.0398(18) -0.0113(15) 0.0063(14) 0.0051(13) C13 0.054(2) 0.0438(19) 0.057(2) -0.0141(17) 0.0271(18) -0.0004(16) C14 0.052(2) 0.049(2) 0.056(2) -0.0192(18) 0.0275(18) -0.0004(16) C15 0.0420(18) 0.0375(17) 0.0452(19) -0.0087(15) 0.0140(15) 0.0042(14) C16 0.0399(18) 0.0409(18) 0.0420(19) -0.0121(15) 0.0131(15) -0.0009(14) C17 0.0349(16) 0.0331(16) 0.0341(16) -0.0111(13) 0.0105(13) 0.0006(12) C18 0.0472(19) 0.0326(17) 0.056(2) -0.0126(16) 0.0244(16) -0.0083(14) C19 0.0458(18) 0.0371(17) 0.0446(19) -0.0099(15) 0.0279(15) -0.0054(14) C20 0.0286(15) 0.0316(15) 0.0242(14) -0.0055(12) 0.0075(12) 0.0031(11) C21 0.083(3) 0.0336(17) 0.048(2) -0.0066(15) 0.0414(19) -0.0062(17) C22 0.085(3) 0.0412(19) 0.048(2) -0.0098(16) 0.045(2) -0.0102(18) C23 0.0352(15) 0.0237(14) 0.0234(14) 0.0009(11) 0.0114(12) -0.0014(11) C24 0.0359(16) 0.0342(16) 0.0336(16) 0.0007(13) 0.0142(13) -0.0008(13) C25 0.0344(16) 0.0445(18) 0.0342(17) 0.0030(14) 0.0050(14) -0.0107(14) C26 0.053(2) 0.0415(18) 0.0299(16) -0.0049(14) 0.0124(15) -0.0177(15) C27 0.054(2) 0.0261(15) 0.0347(16) -0.0059(13) 0.0222(15) -0.0067(13) C28 0.0420(17) 0.0222(14) 0.0298(15) -0.0007(12) 0.0180(13) -0.0046(12) C29 0.0399(16) 0.0219(13) 0.0342(16) 0.0006(12) 0.0184(13) 0.0004(12) C30 0.051(2) 0.0299(16) 0.0461(19) 0.0016(14) 0.0283(16) 0.0074(14) C31 0.0395(18) 0.0375(18) 0.060(2) 0.0127(16) 0.0245(17) 0.0125(14) C32 0.0320(16) 0.0456(19) 0.0448(19) 0.0129(16) 0.0059(14) 0.0042(14) C33 0.0392(17) 0.0364(16) 0.0312(16) 0.0010(13) 0.0111(13) 0.0031(13) C34 0.0304(15) 0.0264(14) 0.0285(15) 0.0019(12) 0.0097(12) 0.0022(11) _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 N1 1.605(3) . ? S1 N2 1.615(3) . ? N1 C5 1.348(4) . ? N2 C6 1.361(4) . ? N3 C23 1.390(3) . ? N3 C34 1.393(3) . ? N3 C20 1.426(3) . ? C1 C2 1.369(4) . ? C1 C6 1.416(4) . ? C1 C7 1.437(4) . ? C2 C3 1.428(4) . ? C2 H2 0.9500 . ? C3 C4 1.363(4) . ? C3 H3 0.9500 . ? C4 C5 1.410(4) . ? C4 H4 0.9500 . ? C5 C6 1.431(4) . ? C7 C8 1.193(4) . ? C8 C9 1.438(4) . ? C9 C10 1.386(4) . ? C9 C14 1.389(5) . ? C10 C11 1.386(4) . ? C10 H10 0.9500 . ? C11 C12 1.396(4) . ? C11 H11 0.9500 . ? C12 C13 1.382(4) . ? C12 C15 1.473(4) . ? C13 C14 1.383(4) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C15 C16 1.313(4) . ? C15 H15 0.9500 . ? C16 C17 1.469(4) . ? C16 H16 0.9500 . ? C17 C18 1.382(4) . ? C17 C22 1.390(4) . ? C18 C19 1.380(4) . ? C18 H18 0.9500 . ? C19 C20 1.365(4) . ? C19 H19 0.9500 . ? C20 C21 1.380(4) . ? C21 C22 1.375(4) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 C24 1.389(4) . ? C23 C28 1.410(4) . ? C24 C25 1.382(4) . ? C24 H24 0.9500 . ? C25 C26 1.399(4) . ? C25 H25 0.9500 . ? C26 C27 1.375(4) . ? C26 H26 0.9500 . ? C27 C28 1.391(4) . ? C27 H27 0.9500 . ? C28 C29 1.440(4) . ? C29 C30 1.402(4) . ? C29 C34 1.405(4) . ? C30 C31 1.366(5) . ? C30 H30 0.9500 . ? C31 C32 1.396(5) . ? C31 H31 0.9500 . ? C32 C33 1.378(4) . ? C32 H32 0.9500 . ? C33 C34 1.388(4) . ? C33 H33 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 N1 S1 N2 101.54(14) . . ? C5 N1 S1 106.8(2) . . ? C6 N2 S1 105.3(2) . . ? C23 N3 C34 108.8(2) . . ? C23 N3 C20 125.9(2) . . ? C34 N3 C20 125.2(2) . . ? C2 C1 C6 116.0(3) . . ? C2 C1 C7 122.0(3) . . ? C6 C1 C7 122.0(3) . . ? C1 C2 C3 124.4(3) . . ? C1 C2 H2 117.8 . . ? C3 C2 H2 117.8 . . ? C4 C3 C2 119.7(3) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 118.2(3) . . ? C3 C4 H4 120.9 . . ? C5 C4 H4 120.9 . . ? N1 C5 C4 126.1(3) . . ? N1 C5 C6 112.6(3) . . ? C4 C5 C6 121.3(3) . . ? N2 C6 C1 126.0(3) . . ? N2 C6 C5 113.7(3) . . ? C1 C6 C5 120.2(3) . . ? C8 C7 C1 176.0(4) . . ? C7 C8 C9 179.0(4) . . ? C10 C9 C14 118.4(3) . . ? C10 C9 C8 120.5(3) . . ? C14 C9 C8 121.1(3) . . ? C9 C10 C11 121.1(3) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C12 120.5(3) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C13 C12 C11 118.1(3) . . ? C13 C12 C15 119.5(3) . . ? C11 C12 C15 122.4(3) . . ? C12 C13 C14 121.5(3) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C13 C14 C9 120.5(3) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? C16 C15 C12 126.8(3) . . ? C16 C15 H15 116.6 . . ? C12 C15 H15 116.6 . . ? C15 C16 C17 127.2(3) . . ? C15 C16 H16 116.4 . . ? C17 C16 H16 116.4 . . ? C18 C17 C22 117.0(3) . . ? C18 C17 C16 119.5(3) . . ? C22 C17 C16 123.5(3) . . ? C19 C18 C17 121.8(3) . . ? C19 C18 H18 119.1 . . ? C17 C18 H18 119.1 . . ? C20 C19 C18 120.1(3) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 119.6(3) . . ? C19 C20 N3 120.9(2) . . ? C21 C20 N3 119.5(3) . . ? C22 C21 C20 119.9(3) . . ? C22 C21 H21 120.1 . . ? C20 C21 H21 120.1 . . ? C21 C22 C17 121.6(3) . . ? C21 C22 H22 119.2 . . ? C17 C22 H22 119.2 . . ? C24 C23 N3 129.3(2) . . ? C24 C23 C28 122.1(3) . . ? N3 C23 C28 108.6(2) . . ? C25 C24 C23 117.7(3) . . ? C25 C24 H24 121.1 . . ? C23 C24 H24 121.1 . . ? C24 C25 C26 121.0(3) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C27 C26 C25 120.8(3) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C28 119.8(3) . . ? C26 C27 H27 120.1 . . ? C28 C27 H27 120.1 . . ? C27 C28 C23 118.6(3) . . ? C27 C28 C29 134.5(3) . . ? C23 C28 C29 106.9(2) . . ? C30 C29 C34 118.9(3) . . ? C30 C29 C28 134.0(3) . . ? C34 C29 C28 107.1(2) . . ? C31 C30 C29 118.5(3) . . ? C31 C30 H30 120.8 . . ? C29 C30 H30 120.8 . . ? C30 C31 C32 121.8(3) . . ? C30 C31 H31 119.1 . . ? C32 C31 H31 119.1 . . ? C33 C32 C31 121.2(3) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C32 C33 C34 117.0(3) . . ? C32 C33 H33 121.5 . . ? C34 C33 H33 121.5 . . ? C33 C34 N3 128.8(3) . . ? C33 C34 C29 122.5(3) . . ? N3 C34 C29 108.6(2) . . ? 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 N2 S1 N1 C5 0.7(3) . . . . ? N1 S1 N2 C6 -0.7(2) . . . . ? C6 C1 C2 C3 1.2(5) . . . . ? C7 C1 C2 C3 -178.7(3) . . . . ? C1 C2 C3 C4 0.9(5) . . . . ? C2 C3 C4 C5 -1.9(5) . . . . ? S1 N1 C5 C4 178.6(3) . . . . ? S1 N1 C5 C6 -0.5(3) . . . . ? C3 C4 C5 N1 -178.1(3) . . . . ? C3 C4 C5 C6 0.9(5) . . . . ? S1 N2 C6 C1 -180.0(3) . . . . ? S1 N2 C6 C5 0.5(3) . . . . ? C2 C1 C6 N2 178.2(3) . . . . ? C7 C1 C6 N2 -1.9(5) . . . . ? C2 C1 C6 C5 -2.2(4) . . . . ? C7 C1 C6 C5 177.6(3) . . . . ? N1 C5 C6 N2 0.0(4) . . . . ? C4 C5 C6 N2 -179.1(3) . . . . ? N1 C5 C6 C1 -179.6(3) . . . . ? C4 C5 C6 C1 1.3(4) . . . . ? C2 C1 C7 C8 30(5) . . . . ? C6 C1 C7 C8 -150(5) . . . . ? C1 C7 C8 C9 62(24) . . . . ? C7 C8 C9 C10 105(22) . . . . ? C7 C8 C9 C14 -74(22) . . . . ? C14 C9 C10 C11 1.0(5) . . . . ? C8 C9 C10 C11 -178.6(3) . . . . ? C9 C10 C11 C12 -0.1(5) . . . . ? C10 C11 C12 C13 -0.9(5) . . . . ? C10 C11 C12 C15 179.4(3) . . . . ? C11 C12 C13 C14 0.9(5) . . . . ? C15 C12 C13 C14 -179.4(3) . . . . ? C12 C13 C14 C9 0.1(5) . . . . ? C10 C9 C14 C13 -1.0(5) . . . . ? C8 C9 C14 C13 178.6(3) . . . . ? C13 C12 C15 C16 -171.1(3) . . . . ? C11 C12 C15 C16 8.6(5) . . . . ? C12 C15 C16 C17 -177.8(3) . . . . ? C15 C16 C17 C18 -176.1(3) . . . . ? C15 C16 C17 C22 5.6(5) . . . . ? C22 C17 C18 C19 -0.8(5) . . . . ? C16 C17 C18 C19 -179.2(3) . . . . ? C17 C18 C19 C20 0.2(5) . . . . ? C18 C19 C20 C21 0.7(5) . . . . ? C18 C19 C20 N3 -179.5(3) . . . . ? C23 N3 C20 C19 -109.9(3) . . . . ? C34 N3 C20 C19 66.1(4) . . . . ? C23 N3 C20 C21 69.9(4) . . . . ? C34 N3 C20 C21 -114.1(3) . . . . ? C19 C20 C21 C22 -0.9(5) . . . . ? N3 C20 C21 C22 179.3(3) . . . . ? C20 C21 C22 C17 0.3(6) . . . . ? C18 C17 C22 C21 0.6(5) . . . . ? C16 C17 C22 C21 178.9(3) . . . . ? C34 N3 C23 C24 178.8(3) . . . . ? C20 N3 C23 C24 -4.6(4) . . . . ? C34 N3 C23 C28 0.3(3) . . . . ? C20 N3 C23 C28 176.8(2) . . . . ? N3 C23 C24 C25 -178.6(3) . . . . ? C28 C23 C24 C25 -0.1(4) . . . . ? C23 C24 C25 C26 -0.1(4) . . . . ? C24 C25 C26 C27 0.1(5) . . . . ? C25 C26 C27 C28 0.0(4) . . . . ? C26 C27 C28 C23 -0.2(4) . . . . ? C26 C27 C28 C29 179.5(3) . . . . ? C24 C23 C28 C27 0.3(4) . . . . ? N3 C23 C28 C27 179.0(2) . . . . ? C24 C23 C28 C29 -179.5(2) . . . . ? N3 C23 C28 C29 -0.8(3) . . . . ? C27 C28 C29 C30 0.8(6) . . . . ? C23 C28 C29 C30 -179.4(3) . . . . ? C27 C28 C29 C34 -178.7(3) . . . . ? C23 C28 C29 C34 1.1(3) . . . . ? C34 C29 C30 C31 0.0(4) . . . . ? C28 C29 C30 C31 -179.5(3) . . . . ? C29 C30 C31 C32 0.9(5) . . . . ? C30 C31 C32 C33 -0.5(5) . . . . ? C31 C32 C33 C34 -0.7(4) . . . . ? C32 C33 C34 N3 -179.2(3) . . . . ? C32 C33 C34 C29 1.6(4) . . . . ? C23 N3 C34 C33 -178.8(3) . . . . ? C20 N3 C34 C33 4.6(4) . . . . ? C23 N3 C34 C29 0.4(3) . . . . ? C20 N3 C34 C29 -176.1(2) . . . . ? C30 C29 C34 C33 -1.2(4) . . . . ? C28 C29 C34 C33 178.4(3) . . . . ? C30 C29 C34 N3 179.5(2) . . . . ? C28 C29 C34 N3 -0.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.303 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.044