# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Joong Suk Oh' _publ_contact_author_email oh.joongsuk@gmail.com loop_ _publ_author_name 'Joong Suk Oh' 'Tae Hee Ryu' 'Jae Heon Lee' 'Choong Eui Song' data_ma _database_code_depnum_ccdc_archive 'CCDC 836783' #TrackingRef 'BCD-TU.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H44 N6 S, C7 H8' _chemical_formula_sum 'C46 H52 N6 S' _chemical_formula_weight 721.00 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) ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.6327(11) _cell_length_b 11.6667(10) _cell_length_c 15.0995(13) _cell_angle_alpha 90.00 _cell_angle_beta 104.810(4) _cell_angle_gamma 90.00 _cell_volume 1981.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9954 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 22.34 _exptl_crystal_description BLOCK _exptl_crystal_colour colourless _exptl_crystal_size_min 0.36 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.46 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 772 _exptl_absorpt_coefficient_mu 0.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9459 _exptl_absorpt_correction_T_max 0.9573 _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 '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 28496 _diffrn_reflns_av_R_equivalents 0.0227 _diffrn_reflns_av_sigmaI/netI 0.0366 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.59 _reflns_number_total 9417 _reflns_number_gt 6530 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.1357P)^2^+0.1308P] 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 0.90(10) _refine_ls_number_reflns 9417 _refine_ls_number_parameters 444 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1018 _refine_ls_R_factor_gt 0.0684 _refine_ls_wR_factor_ref 0.2095 _refine_ls_wR_factor_gt 0.1819 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.67961(8) 0.25390(8) 0.16765(5) 0.0548(2) Uani 1 1 d . . . N1 N 0.5817(4) 0.5851(4) 0.3899(3) 0.0864(11) Uani 1 1 d . . . N2 N 1.0786(3) 0.3724(3) 0.35228(19) 0.0601(8) Uani 1 1 d . . . N3 N 0.8671(2) 0.3895(2) 0.23171(16) 0.0491(6) Uani 1 1 d . . . H3 H 0.9181 0.4381 0.2219 0.059 Uiso 1 1 calc R . . N4 N 0.8319(2) 0.3453(2) 0.08136(15) 0.0395(5) Uani 1 1 d . . . H4 H 0.8967 0.3824 0.0844 0.047 Uiso 1 1 calc R . . N5 N 0.9565(3) 0.0136(3) -0.0884(2) 0.0546(7) Uani 1 1 d . . . N6 N 0.7151(3) 0.5056(2) -0.04571(18) 0.0486(6) Uani 1 1 d . . . C1 C 0.7587(3) 0.4428(3) 0.3465(2) 0.0551(8) Uani 1 1 d . . . C2 C 0.7312(4) 0.5502(4) 0.3085(3) 0.0687(10) Uani 1 1 d . . . H2 H 0.7720 0.5788 0.2677 0.082 Uiso 1 1 calc R . . C3 C 0.6413(5) 0.6169(4) 0.3312(4) 0.0916(17) Uani 1 1 d . . . H3A H 0.6233 0.6877 0.3027 0.110 Uiso 1 1 calc R . . C4 C 0.6071(4) 0.4800(4) 0.4282(3) 0.0710(11) Uani 1 1 d . . . C5 C 0.5454(5) 0.4425(7) 0.4938(4) 0.0987(19) Uani 1 1 d . . . H5 H 0.4899 0.4916 0.5081 0.118 Uiso 1 1 calc R . . C6 C 0.5637(5) 0.3396(6) 0.5358(4) 0.0943(17) Uani 1 1 d . . . H6 H 0.5221 0.3185 0.5784 0.113 Uiso 1 1 calc R . . C7 C 0.6450(4) 0.2669(5) 0.5143(3) 0.0781(12) Uani 1 1 d . . . H7 H 0.6578 0.1956 0.5427 0.094 Uiso 1 1 calc R . . C8 C 0.7081(4) 0.2955(4) 0.4524(3) 0.0656(10) Uani 1 1 d . . . H8 H 0.7615 0.2431 0.4390 0.079 Uiso 1 1 calc R . . C9 C 0.6932(3) 0.4035(4) 0.4088(3) 0.0594(9) Uani 1 1 d . . . C10 C 0.8594(3) 0.3723(3) 0.32619(19) 0.0492(7) Uani 1 1 d . . . H10 H 0.8477 0.2909 0.3370 0.059 Uiso 1 1 calc R . . C11 C 0.9801(3) 0.4137(3) 0.3890(2) 0.0522(8) Uani 1 1 d . . . H11 H 0.9805 0.4976 0.3859 0.063 Uiso 1 1 calc R . . C12 C 1.0006(3) 0.3806(4) 0.4912(2) 0.0672(11) Uani 1 1 d . . . H12A H 1.0102 0.4493 0.5286 0.081 Uiso 1 1 calc R . . H12B H 0.9326 0.3384 0.5000 0.081 Uiso 1 1 calc R . . C13 C 1.1111(4) 0.3076(4) 0.5191(3) 0.0644(10) Uani 1 1 d . . . H13 H 1.1230 0.2814 0.5824 0.077 Uiso 1 1 calc R . . C14 C 1.0964(5) 0.2061(4) 0.4549(4) 0.0912(15) Uani 1 1 d . . . H14A H 1.0252 0.1638 0.4567 0.109 Uiso 1 1 calc R . . H14B H 1.1640 0.1551 0.4741 0.109 Uiso 1 1 calc R . . C15 C 1.0869(4) 0.2478(5) 0.3572(3) 0.0836(13) Uani 1 1 d . . . H15A H 1.1562 0.2229 0.3379 0.100 Uiso 1 1 calc R . . H15B H 1.0171 0.2145 0.3159 0.100 Uiso 1 1 calc R . . C16 C 1.1903(3) 0.4218(4) 0.4084(2) 0.0662(10) Uani 1 1 d . . . H16A H 1.1833 0.5046 0.4091 0.079 Uiso 1 1 calc R . . H16B H 1.2549 0.4028 0.3812 0.079 Uiso 1 1 calc R . . C17 C 1.2194(3) 0.3753(3) 0.5089(2) 0.0577(9) Uani 1 1 d . . . H17 H 1.2846 0.3203 0.5151 0.069 Uiso 1 1 calc R . . C18 C 1.2633(4) 0.4679(4) 0.5783(3) 0.0772(12) Uani 1 1 d . . . H18 H 1.3160 0.5194 0.5627 0.093 Uiso 1 1 calc R . . C19 C 1.2407(5) 0.4872(5) 0.6538(3) 0.0920(16) Uani 1 1 d . . . H19A H 1.1889 0.4395 0.6743 0.110 Uiso 1 1 calc R . . H19B H 1.2758 0.5492 0.6893 0.110 Uiso 1 1 calc R . . C20 C 0.7974(3) 0.3322(2) 0.15816(18) 0.0390(6) Uani 1 1 d . . . C21 C 0.7680(3) 0.3016(2) -0.00661(18) 0.0364(6) Uani 1 1 d . . . H21 H 0.6884 0.2782 -0.0029 0.044 Uiso 1 1 calc R . . C22 C 0.8302(3) 0.1981(2) -0.03461(18) 0.0399(6) Uani 1 1 d . . . C23 C 0.9506(3) 0.1989(3) -0.0204(2) 0.0485(7) Uani 1 1 d . . . H23 H 0.9941 0.2624 0.0065 0.058 Uiso 1 1 calc R . . C24 C 1.0096(3) 0.1044(3) -0.0462(2) 0.0559(8) Uani 1 1 d . . . H24 H 1.0922 0.1066 -0.0322 0.067 Uiso 1 1 calc R . . C25 C 0.8345(3) 0.0098(3) -0.1054(2) 0.0500(7) Uani 1 1 d . . . C26 C 0.7739(4) -0.0856(3) -0.1537(3) 0.0686(11) Uani 1 1 d . . . H26 H 0.8168 -0.1421 -0.1749 0.082 Uiso 1 1 calc R . . C27 C 0.6558(4) -0.0956(3) -0.1694(3) 0.0669(10) Uani 1 1 d . . . H27 H 0.6178 -0.1592 -0.2010 0.080 Uiso 1 1 calc R . . C28 C 0.5882(4) -0.0119(3) -0.1389(3) 0.0616(9) Uani 1 1 d . . . H28 H 0.5064 -0.0208 -0.1493 0.074 Uiso 1 1 calc R . . C29 C 0.6428(3) 0.0825(3) -0.0941(2) 0.0501(7) Uani 1 1 d . . . H29 H 0.5975 0.1374 -0.0739 0.060 Uiso 1 1 calc R . . C30 C 0.7683(3) 0.0989(2) -0.07744(19) 0.0400(6) Uani 1 1 d . . . C31 C 0.7548(3) 0.3978(2) -0.08000(18) 0.0385(6) Uani 1 1 d . . . H31 H 0.8337 0.4117 -0.0898 0.046 Uiso 1 1 calc R . . C32 C 0.6706(3) 0.3650(3) -0.1739(2) 0.0483(7) Uani 1 1 d . . . H32A H 0.7120 0.3724 -0.2218 0.058 Uiso 1 1 calc R . . H32B H 0.6448 0.2861 -0.1725 0.058 Uiso 1 1 calc R . . C33 C 0.5628(3) 0.4453(3) -0.1932(3) 0.0601(9) Uani 1 1 d . . . H33 H 0.5042 0.4216 -0.2492 0.072 Uiso 1 1 calc R . . C34 C 0.5075(3) 0.4417(4) -0.1111(3) 0.0742(11) Uani 1 1 d . . . H34A H 0.4346 0.4860 -0.1243 0.089 Uiso 1 1 calc R . . H34B H 0.4890 0.3632 -0.0986 0.089 Uiso 1 1 calc R . . C35 C 0.5969(4) 0.4916(3) -0.0291(3) 0.0626(10) Uani 1 1 d . . . H35A H 0.5686 0.5657 -0.0144 0.075 Uiso 1 1 calc R . . H35B H 0.6031 0.4417 0.0232 0.075 Uiso 1 1 calc R . . C36 C 0.7062(4) 0.5925(3) -0.1179(2) 0.0577(9) Uani 1 1 d . . . H36A H 0.7797 0.5934 -0.1371 0.069 Uiso 1 1 calc R . . H36B H 0.6963 0.6675 -0.0931 0.069 Uiso 1 1 calc R . . C37 C 0.6014(3) 0.5696(3) -0.2020(2) 0.0563(8) Uani 1 1 d . . . H37 H 0.5355 0.6200 -0.1981 0.068 Uiso 1 1 calc R . . C38 C 0.6330(4) 0.5944(3) -0.2898(3) 0.0669(10) Uani 1 1 d . . . H38 H 0.6917 0.5488 -0.3035 0.080 Uiso 1 1 calc R . . C39 C 0.5874(5) 0.6725(4) -0.3486(3) 0.0842(14) Uani 1 1 d . . . H39A H 0.5284 0.7204 -0.3381 0.101 Uiso 1 1 calc R . . H39B H 0.6136 0.6810 -0.4015 0.101 Uiso 1 1 calc R . . C40 C 0.0036(8) 0.8031(7) 0.2440(6) 0.124(2) Uiso 1 1 d . . . C41 C -0.0822(8) 0.7655(9) 0.2025(6) 0.136(2) Uiso 1 1 d . . . H41 H -0.0980 0.6880 0.2074 0.163 Uiso 1 1 calc R . . C42 C -0.1512(11) 0.8238(11) 0.1533(7) 0.169(4) Uiso 1 1 d . . . H42 H -0.2209 0.7883 0.1211 0.202 Uiso 1 1 calc R . . C43 C -0.1412(11) 0.9459(11) 0.1364(8) 0.169(4) Uiso 1 1 d . . . H43 H -0.1984 0.9862 0.0933 0.203 Uiso 1 1 calc R . . C44 C -0.0539(9) 0.9898(9) 0.1823(6) 0.144(3) Uiso 1 1 d . . . H44 H -0.0448 1.0683 0.1757 0.173 Uiso 1 1 calc R . . C45 C 0.0332(9) 0.9334(8) 0.2434(7) 0.147(3) Uiso 1 1 d . . . H45 H 0.1011 0.9676 0.2799 0.177 Uiso 1 1 calc R . . C46 C 0.0833(14) 0.7225(14) 0.2953(10) 0.226(6) Uiso 1 1 d . . . H46A H 0.1535 0.7612 0.3296 0.339 Uiso 1 1 calc R . . H46B H 0.1047 0.6679 0.2547 0.339 Uiso 1 1 calc R . . H46C H 0.0462 0.6835 0.3367 0.339 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 0.0488(5) 0.0676(5) 0.0502(4) 0.0026(4) 0.0165(3) -0.0166(4) N1 0.074(2) 0.094(3) 0.096(3) -0.025(2) 0.029(2) 0.012(2) N2 0.0424(15) 0.092(2) 0.0455(14) -0.0123(14) 0.0096(12) -0.0028(14) N3 0.0493(15) 0.0613(16) 0.0376(12) -0.0046(11) 0.0126(11) -0.0110(13) N4 0.0380(12) 0.0422(12) 0.0378(11) -0.0010(9) 0.0088(10) -0.0088(10) N5 0.0508(17) 0.0556(16) 0.0590(16) 0.0060(13) 0.0168(13) 0.0190(13) N6 0.0558(16) 0.0412(13) 0.0473(13) -0.0027(11) 0.0103(12) 0.0042(12) C1 0.0495(19) 0.062(2) 0.0490(17) -0.0132(15) 0.0042(15) -0.0035(15) C2 0.069(3) 0.070(2) 0.065(2) -0.0023(18) 0.014(2) 0.003(2) C3 0.084(3) 0.074(3) 0.101(3) -0.018(3) -0.006(3) 0.020(3) C4 0.055(2) 0.079(3) 0.082(3) -0.034(2) 0.0223(19) -0.0049(19) C5 0.064(3) 0.139(5) 0.104(4) -0.063(4) 0.041(3) -0.015(3) C6 0.085(4) 0.125(5) 0.087(3) -0.036(3) 0.048(3) -0.034(3) C7 0.072(3) 0.099(3) 0.069(2) -0.012(2) 0.030(2) -0.022(3) C8 0.054(2) 0.076(2) 0.072(2) -0.0150(19) 0.0260(18) -0.0135(18) C9 0.0414(18) 0.078(2) 0.0591(19) -0.0212(18) 0.0132(15) -0.0044(17) C10 0.0413(16) 0.072(2) 0.0359(14) -0.0015(14) 0.0130(12) -0.0008(15) C11 0.0464(18) 0.070(2) 0.0384(14) -0.0082(14) 0.0077(13) 0.0024(15) C12 0.0483(19) 0.115(3) 0.0396(15) -0.0019(19) 0.0130(14) -0.001(2) C13 0.062(2) 0.074(2) 0.0528(19) 0.0079(18) 0.0065(17) -0.0045(18) C14 0.092(4) 0.066(2) 0.103(4) -0.006(2) 0.002(3) -0.003(2) C15 0.063(2) 0.095(3) 0.087(3) -0.038(3) 0.010(2) 0.009(2) C16 0.046(2) 0.097(3) 0.0556(19) -0.0008(19) 0.0139(16) -0.0078(19) C17 0.0433(18) 0.074(2) 0.0527(18) -0.0059(16) 0.0058(14) 0.0030(16) C18 0.073(3) 0.091(3) 0.066(2) -0.013(2) 0.015(2) -0.016(2) C19 0.096(4) 0.120(4) 0.056(2) -0.022(3) 0.014(2) -0.015(3) C20 0.0408(15) 0.0373(13) 0.0379(13) 0.0023(11) 0.0079(12) 0.0017(11) C21 0.0320(14) 0.0404(13) 0.0358(13) -0.0012(10) 0.0065(11) -0.0007(11) C22 0.0414(16) 0.0412(14) 0.0347(13) 0.0060(11) 0.0051(12) 0.0036(12) C23 0.0408(17) 0.0478(16) 0.0559(17) -0.0006(14) 0.0104(14) 0.0062(13) C24 0.0419(17) 0.064(2) 0.0606(19) 0.0044(17) 0.0118(15) 0.0132(16) C25 0.058(2) 0.0427(15) 0.0479(16) -0.0026(13) 0.0110(15) 0.0076(14) C26 0.088(3) 0.0392(17) 0.077(2) -0.0080(16) 0.019(2) 0.0096(18) C27 0.079(3) 0.0499(19) 0.067(2) -0.0153(17) 0.009(2) -0.0094(19) C28 0.061(2) 0.054(2) 0.067(2) -0.0033(17) 0.0104(18) -0.0135(17) C29 0.0485(18) 0.0419(15) 0.0572(18) -0.0038(13) 0.0085(14) -0.0013(13) C30 0.0413(15) 0.0392(14) 0.0396(14) 0.0047(11) 0.0105(12) 0.0001(12) C31 0.0372(14) 0.0407(14) 0.0375(13) 0.0012(11) 0.0091(11) 0.0016(12) C32 0.0533(19) 0.0458(15) 0.0403(14) -0.0004(12) 0.0019(13) 0.0001(14) C33 0.049(2) 0.060(2) 0.0607(19) 0.0116(16) -0.0044(16) 0.0001(16) C34 0.0406(19) 0.081(3) 0.104(3) 0.025(2) 0.025(2) 0.0044(18) C35 0.065(2) 0.058(2) 0.070(2) 0.0076(17) 0.0265(19) 0.0216(18) C36 0.072(2) 0.0423(16) 0.0563(18) 0.0051(14) 0.0112(17) 0.0033(16) C37 0.0482(19) 0.0545(18) 0.0609(19) 0.0112(15) 0.0041(15) 0.0151(15) C38 0.078(3) 0.054(2) 0.068(2) 0.0105(18) 0.018(2) 0.0079(19) C39 0.101(4) 0.074(3) 0.063(2) 0.000(2) -0.007(2) -0.008(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 C20 1.683(3) . ? N1 C3 1.311(7) . ? N1 C4 1.355(7) . ? N2 C15 1.457(6) . ? N2 C11 1.475(5) . ? N2 C16 1.475(5) . ? N3 C20 1.370(4) . ? N3 C10 1.466(4) . ? N3 H3 0.8600 . ? N4 C20 1.329(4) . ? N4 C21 1.440(3) . ? N4 H4 0.8600 . ? N5 C24 1.307(5) . ? N5 C25 1.377(5) . ? N6 C35 1.468(5) . ? N6 C36 1.473(4) . ? N6 C31 1.478(4) . ? C1 C2 1.382(6) . ? C1 C9 1.429(6) . ? C1 C10 1.525(5) . ? C2 C3 1.415(7) . ? C2 H2 0.9300 . ? C3 H3A 0.9300 . ? C4 C9 1.427(6) . ? C4 C5 1.431(8) . ? C5 C6 1.349(9) . ? C5 H5 0.9300 . ? C6 C7 1.370(8) . ? C6 H6 0.9300 . ? C7 C8 1.368(6) . ? C7 H7 0.9300 . ? C8 C9 1.412(6) . ? C8 H8 0.9300 . ? C10 C11 1.556(5) . ? C10 H10 0.9800 . ? C11 C12 1.548(5) . ? C11 H11 0.9800 . ? C12 C13 1.510(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.512(7) . ? C13 C17 1.528(6) . ? C13 H13 0.9800 . ? C14 C15 1.530(8) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.565(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.499(6) . ? C17 H17 0.9800 . ? C18 C19 1.255(7) . ? C18 H18 0.9300 . ? C19 H19A 0.9300 . ? C19 H19B 0.9300 . ? C21 C22 1.521(4) . ? C21 C31 1.557(4) . ? C21 H21 0.9800 . ? C22 C23 1.362(5) . ? C22 C30 1.428(4) . ? C23 C24 1.405(5) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? C25 C26 1.416(5) . ? C25 C30 1.421(4) . ? C26 C27 1.339(6) . ? C26 H26 0.9300 . ? C27 C28 1.403(6) . ? C27 H27 0.9300 . ? C28 C29 1.361(5) . ? C28 H28 0.9300 . ? C29 C30 1.430(5) . ? C29 H29 0.9300 . ? C31 C32 1.551(4) . ? C31 H31 0.9800 . ? C32 C33 1.533(5) . ? C32 H32A 0.9700 . ? C32 H32B 0.9700 . ? C33 C37 1.533(5) . ? C33 C34 1.536(6) . ? C33 H33 0.9800 . ? C34 C35 1.515(6) . ? C34 H34A 0.9700 . ? C34 H34B 0.9700 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 C37 1.543(5) . ? C36 H36A 0.9700 . ? C36 H36B 0.9700 . ? C37 C38 1.492(6) . ? C37 H37 0.9800 . ? C38 C39 1.287(6) . ? C38 H38 0.9300 . ? C39 H39A 0.9300 . ? C39 H39B 0.9300 . ? C40 C41 1.123(10) . ? C40 C46 1.406(15) . ? C40 C45 1.559(13) . ? C40 C42 1.978(15) . ? C41 C42 1.163(12) . ? C41 H41 0.9300 . ? C42 C43 1.457(16) . ? C42 H42 0.9300 . ? C43 C44 1.190(13) . ? C43 H43 0.9300 . ? C44 C45 1.353(12) . ? C44 H44 0.9300 . ? C45 H45 0.9300 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 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 C3 N1 C4 116.7(4) . . ? C15 N2 C11 110.7(3) . . ? C15 N2 C16 108.8(3) . . ? C11 N2 C16 108.1(3) . . ? C20 N3 C10 123.5(3) . . ? C20 N3 H3 118.3 . . ? C10 N3 H3 118.3 . . ? C20 N4 C21 124.3(2) . . ? C20 N4 H4 117.8 . . ? C21 N4 H4 117.8 . . ? C24 N5 C25 117.0(3) . . ? C35 N6 C36 108.1(3) . . ? C35 N6 C31 110.8(3) . . ? C36 N6 C31 107.2(2) . . ? C2 C1 C9 117.3(4) . . ? C2 C1 C10 120.9(4) . . ? C9 C1 C10 121.7(3) . . ? C1 C2 C3 120.4(5) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? N1 C3 C2 124.0(5) . . ? N1 C3 H3A 118.0 . . ? C2 C3 H3A 118.0 . . ? N1 C4 C9 124.4(4) . . ? N1 C4 C5 118.6(4) . . ? C9 C4 C5 116.9(5) . . ? C6 C5 C4 123.5(5) . . ? C6 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C5 C6 C7 118.2(5) . . ? C5 C6 H6 120.9 . . ? C7 C6 H6 120.9 . . ? C8 C7 C6 122.3(5) . . ? C8 C7 H7 118.8 . . ? C6 C7 H7 118.8 . . ? C7 C8 C9 120.8(4) . . ? C7 C8 H8 119.6 . . ? C9 C8 H8 119.6 . . ? C8 C9 C4 118.1(4) . . ? C8 C9 C1 124.8(3) . . ? C4 C9 C1 117.1(4) . . ? N3 C10 C1 111.3(3) . . ? N3 C10 C11 106.3(3) . . ? C1 C10 C11 109.3(3) . . ? N3 C10 H10 110.0 . . ? C1 C10 H10 110.0 . . ? C11 C10 H10 110.0 . . ? N2 C11 C12 110.9(3) . . ? N2 C11 C10 109.6(2) . . ? C12 C11 C10 114.6(3) . . ? N2 C11 H11 107.1 . . ? C12 C11 H11 107.1 . . ? C10 C11 H11 107.1 . . ? C13 C12 C11 108.8(3) . . ? C13 C12 H12A 109.9 . . ? C11 C12 H12A 109.9 . . ? C13 C12 H12B 109.9 . . ? C11 C12 H12B 109.9 . . ? H12A C12 H12B 108.3 . . ? C12 C13 C14 108.3(3) . . ? C12 C13 C17 110.2(3) . . ? C14 C13 C17 107.6(4) . . ? C12 C13 H13 110.2 . . ? C14 C13 H13 110.2 . . ? C17 C13 H13 110.2 . . ? C13 C14 C15 109.7(4) . . ? C13 C14 H14A 109.7 . . ? C15 C14 H14A 109.7 . . ? C13 C14 H14B 109.7 . . ? C15 C14 H14B 109.7 . . ? H14A C14 H14B 108.2 . . ? N2 C15 C14 110.8(4) . . ? N2 C15 H15A 109.5 . . ? C14 C15 H15A 109.5 . . ? N2 C15 H15B 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 108.1 . . ? N2 C16 C17 111.3(3) . . ? N2 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? N2 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C13 116.4(3) . . ? C18 C17 C16 112.2(4) . . ? C13 C17 C16 107.2(3) . . ? C18 C17 H17 106.8 . . ? C13 C17 H17 106.8 . . ? C16 C17 H17 106.8 . . ? C19 C18 C17 130.6(5) . . ? C19 C18 H18 114.7 . . ? C17 C18 H18 114.7 . . ? C18 C19 H19A 120.0 . . ? C18 C19 H19B 120.0 . . ? H19A C19 H19B 120.0 . . ? N4 C20 N3 113.8(3) . . ? N4 C20 S1 124.8(2) . . ? N3 C20 S1 121.5(2) . . ? N4 C21 C22 111.5(2) . . ? N4 C21 C31 109.5(2) . . ? C22 C21 C31 110.0(2) . . ? N4 C21 H21 108.6 . . ? C22 C21 H21 108.6 . . ? C31 C21 H21 108.6 . . ? C23 C22 C30 117.1(3) . . ? C23 C22 C21 119.6(3) . . ? C30 C22 C21 123.2(3) . . ? C22 C23 C24 120.4(3) . . ? C22 C23 H23 119.8 . . ? C24 C23 H23 119.8 . . ? N5 C24 C23 124.6(3) . . ? N5 C24 H24 117.7 . . ? C23 C24 H24 117.7 . . ? N5 C25 C26 118.3(3) . . ? N5 C25 C30 122.1(3) . . ? C26 C25 C30 119.6(3) . . ? C27 C26 C25 120.8(4) . . ? C27 C26 H26 119.6 . . ? C25 C26 H26 119.6 . . ? C26 C27 C28 121.2(3) . . ? C26 C27 H27 119.4 . . ? C28 C27 H27 119.4 . . ? C29 C28 C27 119.7(4) . . ? C29 C28 H28 120.1 . . ? C27 C28 H28 120.1 . . ? C28 C29 C30 121.5(3) . . ? C28 C29 H29 119.3 . . ? C30 C29 H29 119.3 . . ? C25 C30 C22 118.7(3) . . ? C25 C30 C29 117.1(3) . . ? C22 C30 C29 124.2(3) . . ? N6 C31 C32 110.4(2) . . ? N6 C31 C21 110.3(2) . . ? C32 C31 C21 113.4(2) . . ? N6 C31 H31 107.5 . . ? C32 C31 H31 107.5 . . ? C21 C31 H31 107.5 . . ? C33 C32 C31 108.6(3) . . ? C33 C32 H32A 110.0 . . ? C31 C32 H32A 110.0 . . ? C33 C32 H32B 110.0 . . ? C31 C32 H32B 110.0 . . ? H32A C32 H32B 108.4 . . ? C32 C33 C37 110.6(3) . . ? C32 C33 C34 108.6(3) . . ? C37 C33 C34 106.7(3) . . ? C32 C33 H33 110.3 . . ? C37 C33 H33 110.3 . . ? C34 C33 H33 110.3 . . ? C35 C34 C33 107.9(3) . . ? C35 C34 H34A 110.1 . . ? C33 C34 H34A 110.1 . . ? C35 C34 H34B 110.1 . . ? C33 C34 H34B 110.1 . . ? H34A C34 H34B 108.4 . . ? N6 C35 C34 112.4(3) . . ? N6 C35 H35A 109.1 . . ? C34 C35 H35A 109.1 . . ? N6 C35 H35B 109.1 . . ? C34 C35 H35B 109.1 . . ? H35A C35 H35B 107.9 . . ? N6 C36 C37 112.4(3) . . ? N6 C36 H36A 109.1 . . ? C37 C36 H36A 109.1 . . ? N6 C36 H36B 109.1 . . ? C37 C36 H36B 109.1 . . ? H36A C36 H36B 107.9 . . ? C38 C37 C33 113.9(3) . . ? C38 C37 C36 112.0(3) . . ? C33 C37 C36 106.3(3) . . ? C38 C37 H37 108.2 . . ? C33 C37 H37 108.2 . . ? C36 C37 H37 108.2 . . ? C39 C38 C37 126.7(4) . . ? C39 C38 H38 116.6 . . ? C37 C38 H38 116.6 . . ? C38 C39 H39A 120.0 . . ? C38 C39 H39B 120.0 . . ? H39A C39 H39B 120.0 . . ? C41 C40 C46 114.4(11) . . ? C41 C40 C45 122.9(10) . . ? C46 C40 C45 122.7(10) . . ? C41 C40 C42 30.7(7) . . ? C46 C40 C42 144.9(9) . . ? C45 C40 C42 92.3(7) . . ? C40 C41 C42 119.9(12) . . ? C40 C41 H41 120.1 . . ? C42 C41 H41 120.1 . . ? C41 C42 C43 127.6(13) . . ? C41 C42 C40 29.5(6) . . ? C43 C42 C40 98.2(9) . . ? C41 C42 H42 116.2 . . ? C43 C42 H42 116.2 . . ? C40 C42 H42 145.7 . . ? C44 C43 C42 114.4(12) . . ? C44 C43 H43 122.8 . . ? C42 C43 H43 122.8 . . ? C43 C44 C45 124.5(11) . . ? C43 C44 H44 117.8 . . ? C45 C44 H44 117.8 . . ? C44 C45 C40 110.5(9) . . ? C44 C45 H45 124.7 . . ? C40 C45 H45 124.7 . . ? C40 C46 H46A 109.5 . . ? C40 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C40 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 28.59 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.643 _refine_diff_density_min -0.401 _refine_diff_density_rms 0.060