# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 #TrackingRef '- compounds_3_4_6.cif' # #------------------------------------------------------------------------- #2 Person making the deposition # _publ_contact_author 'Burzlaff, Nicolai' _publ_contact_author_email burzlaff@chemie.uni-erlangen.de _journal_volume ? _journal_page_first ? _journal_page_last ? _journal_year ? _ccdc_journal_depnumber ? # #------------------------------------------------------------------------- #4 Chemical and physical data # # Note that the units for melting point are Kelvin # The compound_id is the identifier for the compound in the published # paper, eg. 4a, II, etc. # Provide a brief description of any significant biological activity, # eg. antimalarial activity # If the compound exhibits polymorphism provide brief details, # eg. monoclinic form, low-temperature phase, etc. # For chemdiag leave blank - no longer necessary _ccdc_compound_id ? _ccdc_biological_activity ? _ccdc_polymorph ? _ccdc_chemdiag_type ? _ccdc_chemdiag_records ; ? ; # #------------------------------------------------------------------------- #5 Other data relating to the structure determination and refinement # # Record the radiation type if not X-rays, eg. neutron # Record the temperature of the data collection (Kelvin) # if not room-temperature # Record R_squared if this is the only reliability factor given by # your refinement program # Describe briefly any disorder, eg. t-Butyl C31-33 disordered over # two sites with occupancies 0.6 and 0.4 # Under ccdc_comments record any other important information _ccdc_temp_data_collection ? _ccdc_ls_R_squared ? _ccdc_disorder ? _ccdc_comments ; ? ; _publ_author_name N.Burzlaff _publ_contact_author_name 'Burzlaff, Nicolai' # Attachment '- compounds_3_4_6.cif' data_tgbu03 _database_code_depnum_ccdc_archive 'CCDC 807802' #TrackingRef '- compounds_3_4_6.cif' _audit_creation_date 2009-11-22T22:48:09-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H36 N6' _chemical_formula_sum 'C27 H36 N6' _chemical_formula_weight 444.62 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 25.4805(12) _cell_length_b 7.7565(5) _cell_length_c 17.8684(7) _cell_angle_alpha 90 _cell_angle_beta 133.701(3) _cell_angle_gamma 90 _cell_volume 2553.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 136 _cell_measurement_theta_min 6 _cell_measurement_theta_max 20 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.16 _exptl_crystal_density_diffrn 1.157 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker-AXS, 2002' _exptl_absorpt_correction_T_min 0.952022 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_detector_area_resol_mean 9 _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method ; \f- and \w-rotations with 2.00 \% and 100 sec per frame ; _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_unetI/netI 0.0263 _diffrn_reflns_number 39319 _diffrn_reflns_limit_h_min -34 _diffrn_reflns_limit_h_max 34 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.85 _diffrn_reflns_theta_max 28.52 _diffrn_reflns_theta_full 28.52 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 3470 _reflns_number_gt 2971 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'COLLECT (Bruker-Nonius, 2002)' _computing_cell_refinement 'EVALCCD (Duisenberg, 2003)' _computing_data_reduction 'EVALCCD (Duisenberg, 2003)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1986)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0699P)^2^+0.6097P] 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_number_reflns 3470 _refine_ls_number_parameters 298 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0423 _refine_ls_wR_factor_ref 0.1141 _refine_ls_wR_factor_gt 0.1074 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_diff_density_max 0.241 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.048 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.08535(10) 0.6440(2) 0.15127(15) 0.0176(4) Uani 1 1 d . . . H1 H 0.0698 0.6818 0.0861 0.021 Uiso 1 1 calc R . . C2 C 0.07353(10) 0.4524(3) 0.14540(16) 0.0209(4) Uani 1 1 d . . . C3 C 0.05574(14) 0.1973(3) 0.1677(2) 0.0406(6) Uani 1 1 d . . . H3 H 0.0422 0.1061 0.1852 0.049 Uiso 1 1 calc R . . C4 C 0.08445(14) 0.1792(3) 0.1274(2) 0.0400(6) Uani 1 1 d . . . H4 H 0.0945 0.0764 0.1126 0.048 Uiso 1 1 calc R . . C5 C 0.12979(14) 0.3904(4) 0.0744(2) 0.0358(5) Uani 1 1 d . . . H5A H 0.0935 0.4359 0.0055 0.054 Uiso 1 1 calc R . . H5B H 0.1515 0.29 0.0737 0.054 Uiso 1 1 calc R . . H5C H 0.1665 0.4761 0.1191 0.054 Uiso 1 1 calc R . . C11 C 0.21329(11) 0.5828(3) 0.32225(16) 0.0238(4) Uani 1 1 d . . . H11 H 0.2065 0.4767 0.3388 0.029 Uiso 1 1 calc R . . C12 C 0.27625(11) 0.6754(3) 0.37996(15) 0.0230(4) Uani 1 1 d . . . C13 C 0.25825(10) 0.8232(3) 0.32166(15) 0.0213(4) Uani 1 1 d . . . C14 C 0.32505(12) 0.9321(3) 0.37810(18) 0.0338(5) Uani 1 1 d . . . C15 C 0.37374(14) 0.8234(5) 0.3721(2) 0.0529(8) Uani 1 1 d . . . H15A H 0.347 0.7916 0.3011 0.064 Uiso 1 1 calc R . . H15B H 0.4166 0.888 0.3997 0.064 Uiso 1 1 calc R . . C16 C 0.39493(14) 0.6622(5) 0.4383(3) 0.0529(8) Uani 1 1 d . . . H16A H 0.4471 0.6552 0.4962 0.064 Uiso 1 1 calc R . . H16B H 0.378 0.5579 0.3972 0.064 Uiso 1 1 calc R . . C17 C 0.35639(12) 0.6892(4) 0.47592(18) 0.0340(5) Uani 1 1 d . . . H17 H 0.3741 0.6187 0.5351 0.041 Uiso 1 1 calc R . . C18 C 0.36225(13) 0.8883(4) 0.49219(18) 0.0334(5) Uani 1 1 d . . . C19 C 0.32023(16) 0.9541(5) 0.5181(2) 0.0531(8) Uani 1 1 d . . . H19A H 0.271 0.9138 0.467 0.08 Uiso 1 1 calc R . . H19B H 0.3206 1.0779 0.5186 0.08 Uiso 1 1 calc R . . H19C H 0.3425 0.9123 0.5851 0.08 Uiso 1 1 calc R . . C20 C 0.44032(15) 0.9558(5) 0.5755(2) 0.0526(8) Uani 1 1 d . . . H20A H 0.4683 0.9149 0.5614 0.079 Uiso 1 1 calc R . . H20B H 0.4616 0.9152 0.6422 0.079 Uiso 1 1 calc R . . H20C H 0.4399 1.0796 0.575 0.079 Uiso 1 1 calc R . . C21 C 0.31333(18) 1.1182(4) 0.3458(3) 0.0662(11) Uani 1 1 d . . . H21A H 0.3594 1.1751 0.3869 0.099 Uiso 1 1 calc R . . H21B H 0.2849 1.1737 0.356 0.099 Uiso 1 1 calc R . . H21C H 0.2882 1.1246 0.2741 0.099 Uiso 1 1 calc R . . C31 C 0.05897(10) 0.7616(3) 0.25510(14) 0.0211(4) Uani 1 1 d . . . H31 H 0.1037 0.745 0.3222 0.025 Uiso 1 1 calc R . . C32 C -0.00412(10) 0.8150(3) 0.22606(15) 0.0207(4) Uani 1 1 d . . . C33 C -0.05515(10) 0.8166(3) 0.11758(15) 0.0197(4) Uani 1 1 d . . . C34 C -0.12689(11) 0.8787(3) 0.07740(16) 0.0247(4) Uani 1 1 d . . . C35 C -0.11339(14) 1.0730(3) 0.1084(2) 0.0355(5) Uani 1 1 d . . . H35A H -0.1582 1.1294 0.0789 0.043 Uiso 1 1 calc R . . H35B H -0.0935 1.132 0.0848 0.043 Uiso 1 1 calc R . . C36 C -0.05788(15) 1.0721(4) 0.2290(2) 0.0394(6) Uani 1 1 d . . . H36A H -0.0135 1.1318 0.2591 0.047 Uiso 1 1 calc R . . H36B H -0.0783 1.1255 0.2533 0.047 Uiso 1 1 calc R . . C37 C -0.04373(12) 0.8773(3) 0.25582(17) 0.0309(5) Uani 1 1 d . . . H37 H -0.0217 0.8466 0.3257 0.037 Uiso 1 1 calc R . . C38 C -0.12057(12) 0.7971(4) 0.16420(19) 0.0330(6) Uani 1 1 d . . . C39 C -0.12091(16) 0.5998(4) 0.1638(3) 0.0504(8) Uani 1 1 d . . . H39A H -0.0839 0.5582 0.167 0.076 Uiso 1 1 calc R . . H39B H -0.1674 0.559 0.1015 0.076 Uiso 1 1 calc R . . H39C H -0.1116 0.5583 0.2227 0.076 Uiso 1 1 calc R . . C40 C -0.18000(14) 0.8623(5) 0.1595(2) 0.0521(8) Uani 1 1 d . . . H40A H -0.18 0.9861 0.16 0.078 Uiso 1 1 calc R . . H40B H -0.1705 0.82 0.2184 0.078 Uiso 1 1 calc R . . H40C H -0.2265 0.8215 0.0971 0.078 Uiso 1 1 calc R . . C41 C -0.19387(11) 0.8392(5) -0.03453(18) 0.0414(7) Uani 1 1 d . . . H41A H -0.2359 0.8851 -0.0513 0.062 Uiso 1 1 calc R . . H41B H -0.199 0.7166 -0.0448 0.062 Uiso 1 1 calc R . . H41C H -0.1892 0.8908 -0.0785 0.062 Uiso 1 1 calc R . . N1 N 0.04882(10) 0.3699(2) 0.17990(16) 0.0303(4) Uani 1 1 d . . . N2 N 0.09605(10) 0.3436(2) 0.11258(14) 0.0269(4) Uani 1 1 d . . . N11 N 0.18947(9) 0.8300(2) 0.23281(13) 0.0221(4) Uani 1 1 d . . . N12 N 0.16214(8) 0.6793(2) 0.23464(12) 0.0179(3) Uani 1 1 d . . . N31 N -0.02864(8) 0.7692(2) 0.07845(12) 0.0203(3) Uani 1 1 d . . . N32 N 0.04295(8) 0.7375(2) 0.16538(12) 0.0175(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0144(8) 0.0166(9) 0.0189(9) 0.0004(7) 0.0104(8) 0.0003(7) C2 0.0131(9) 0.0185(9) 0.0245(10) -0.0009(8) 0.0104(8) -0.0003(7) C3 0.0420(14) 0.0206(11) 0.0585(17) 0.0040(11) 0.0344(14) -0.0043(11) C4 0.0394(14) 0.0173(11) 0.0567(17) -0.0025(11) 0.0308(14) 0.0014(10) C5 0.0368(13) 0.0344(13) 0.0460(14) -0.0049(11) 0.0323(12) 0.0033(10) C11 0.0192(9) 0.0223(10) 0.0238(10) 0.0060(8) 0.0126(8) 0.0021(8) C12 0.0173(9) 0.0257(10) 0.0215(9) 0.0005(8) 0.0117(8) -0.0003(8) C13 0.0209(9) 0.0239(9) 0.0223(9) -0.0039(8) 0.0161(8) -0.0056(8) C14 0.0243(11) 0.0404(14) 0.0280(11) -0.0060(10) 0.0148(9) -0.0152(10) C15 0.0321(13) 0.087(2) 0.0516(16) -0.0193(18) 0.0336(13) -0.0223(15) C16 0.0227(12) 0.063(2) 0.0611(18) -0.0158(16) 0.0243(13) -0.0018(12) C17 0.0165(10) 0.0409(13) 0.0266(11) 0.0002(10) 0.0080(9) -0.0028(10) C18 0.0229(11) 0.0410(14) 0.0244(11) -0.0080(10) 0.0118(10) -0.0071(10) C19 0.0434(15) 0.074(2) 0.0348(14) -0.0254(15) 0.0242(13) -0.0081(16) C20 0.0300(13) 0.0560(18) 0.0388(14) -0.0164(14) 0.0113(12) -0.0169(14) C21 0.0503(18) 0.0491(19) 0.0524(18) 0.0045(15) 0.0177(15) -0.0306(15) C31 0.0188(9) 0.0218(9) 0.0163(8) 0.0019(8) 0.0098(8) 0.0019(8) C32 0.0206(9) 0.0210(9) 0.0198(9) 0.0019(8) 0.0136(8) 0.0014(8) C33 0.0174(9) 0.0186(9) 0.0204(9) 0.0017(8) 0.0120(8) 0.0008(7) C34 0.0188(9) 0.0337(11) 0.0220(10) 0.0046(9) 0.0143(9) 0.0070(8) C35 0.0367(12) 0.0325(13) 0.0397(13) 0.0107(10) 0.0273(11) 0.0162(10) C36 0.0413(14) 0.0395(15) 0.0417(14) -0.0065(12) 0.0303(13) 0.0084(12) C37 0.0287(11) 0.0457(14) 0.0237(10) 0.0067(10) 0.0202(10) 0.0095(10) C38 0.0248(11) 0.0470(16) 0.0341(11) 0.0123(11) 0.0229(10) 0.0085(10) C39 0.0389(15) 0.0492(17) 0.0664(19) 0.0170(15) 0.0376(15) -0.0018(13) C40 0.0358(14) 0.087(2) 0.0509(15) 0.0186(16) 0.0364(13) 0.0158(15) C41 0.0179(10) 0.0666(19) 0.0289(11) -0.0025(13) 0.0121(10) 0.0101(12) N1 0.0271(9) 0.0231(10) 0.0417(11) 0.0016(8) 0.0241(9) -0.0030(8) N2 0.0248(9) 0.0182(9) 0.0356(10) -0.0031(8) 0.0201(9) 0.0008(7) N11 0.0208(8) 0.0218(8) 0.0204(8) -0.0010(7) 0.0130(7) -0.0060(7) N12 0.0152(7) 0.0168(7) 0.0185(8) 0.0011(7) 0.0104(7) -0.0012(6) N31 0.0151(7) 0.0228(8) 0.0185(7) 0.0004(7) 0.0098(6) 0.0031(7) N32 0.0151(7) 0.0171(8) 0.0170(7) 0.0009(6) 0.0098(7) 0.0012(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N12 1.447(2) . ? C1 N32 1.461(2) . ? C1 C2 1.505(3) . ? C1 H1 0.98 . ? C2 N1 1.312(3) . ? C2 N2 1.361(3) . ? C3 C4 1.342(4) . ? C3 N1 1.387(3) . ? C3 H3 0.93 . ? C4 N2 1.375(3) . ? C4 H4 0.93 . ? C5 N2 1.465(3) . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C11 C12 1.366(3) . ? C11 N12 1.375(3) . ? C11 H11 0.93 . ? C12 C13 1.396(3) . ? C12 C17 1.511(3) . ? C13 N11 1.323(3) . ? C13 C14 1.502(3) . ? C14 C21 1.506(4) . ? C14 C15 1.564(4) . ? C14 C18 1.581(3) . ? C15 C16 1.541(5) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 C17 1.541(4) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C18 1.559(4) . ? C17 H17 0.98 . ? C18 C19 1.519(4) . ? C18 C20 1.535(3) . ? C19 H19A 0.96 . ? C19 H19B 0.96 . ? C19 H19C 0.96 . ? C20 H20A 0.96 . ? C20 H20B 0.96 . ? C20 H20C 0.96 . ? C21 H21A 0.96 . ? C21 H21B 0.96 . ? C21 H21C 0.96 . ? C31 N32 1.367(3) . ? C31 C32 1.368(3) . ? C31 H31 0.93 . ? C32 C33 1.402(3) . ? C32 C37 1.509(3) . ? C33 N31 1.316(3) . ? C33 C34 1.509(3) . ? C34 C41 1.513(3) . ? C34 C35 1.559(3) . ? C34 C38 1.577(3) . ? C35 C36 1.560(4) . ? C35 H35A 0.97 . ? C35 H35B 0.97 . ? C36 C37 1.550(4) . ? C36 H36A 0.97 . ? C36 H36B 0.97 . ? C37 C38 1.572(3) . ? C37 H37 0.98 . ? C38 C39 1.531(4) . ? C38 C40 1.543(3) . ? C39 H39A 0.96 . ? C39 H39B 0.96 . ? C39 H39C 0.96 . ? C40 H40A 0.96 . ? C40 H40B 0.96 . ? C40 H40C 0.96 . ? C41 H41A 0.96 . ? C41 H41B 0.96 . ? C41 H41C 0.96 . ? N11 N12 1.373(2) . ? N31 N32 1.373(2) . ? 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 N12 C1 N32 111.31(15) . . ? N12 C1 C2 108.76(16) . . ? N32 C1 C2 111.46(16) . . ? N12 C1 H1 108.4 . . ? N32 C1 H1 108.4 . . ? C2 C1 H1 108.4 . . ? N1 C2 N2 112.45(19) . . ? N1 C2 C1 125.92(19) . . ? N2 C2 C1 121.25(18) . . ? C4 C3 N1 111.2(2) . . ? C4 C3 H3 124.4 . . ? N1 C3 H3 124.4 . . ? C3 C4 N2 106.0(2) . . ? C3 C4 H4 127 . . ? N2 C4 H4 127 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C12 C11 N12 105.55(18) . . ? C12 C11 H11 127.2 . . ? N12 C11 H11 127.2 . . ? C11 C12 C13 105.03(17) . . ? C11 C12 C17 148.8(2) . . ? C13 C12 C17 106.14(19) . . ? N11 C13 C12 114.10(18) . . ? N11 C13 C14 136.9(2) . . ? C12 C13 C14 108.98(18) . . ? C13 C14 C21 116.7(2) . . ? C13 C14 C15 103.6(2) . . ? C21 C14 C15 116.6(3) . . ? C13 C14 C18 97.85(18) . . ? C21 C14 C18 118.9(2) . . ? C15 C14 C18 100.1(2) . . ? C16 C15 C14 105.0(2) . . ? C16 C15 H15A 110.7 . . ? C14 C15 H15A 110.7 . . ? C16 C15 H15B 110.7 . . ? C14 C15 H15B 110.7 . . ? H15A C15 H15B 108.8 . . ? C15 C16 C17 103.5(2) . . ? C15 C16 H16A 111.1 . . ? C17 C16 H16A 111.1 . . ? C15 C16 H16B 111.1 . . ? C17 C16 H16B 111.1 . . ? H16A C16 H16B 109 . . ? C12 C17 C16 105.3(2) . . ? C12 C17 C18 99.3(2) . . ? C16 C17 C18 102.0(2) . . ? C12 C17 H17 116 . . ? C16 C17 H17 116 . . ? C18 C17 H17 116 . . ? C19 C18 C20 107.7(2) . . ? C19 C18 C17 113.1(2) . . ? C20 C18 C17 114.3(2) . . ? C19 C18 C14 113.6(2) . . ? C20 C18 C14 113.5(2) . . ? C17 C18 C14 94.45(19) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C14 C21 H21A 109.5 . . ? C14 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C14 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N32 C31 C32 106.02(16) . . ? N32 C31 H31 127 . . ? C32 C31 H31 127 . . ? C31 C32 C33 104.55(17) . . ? C31 C32 C37 149.31(19) . . ? C33 C32 C37 106.10(16) . . ? N31 C33 C32 113.95(17) . . ? N31 C33 C34 137.24(18) . . ? C32 C33 C34 108.79(16) . . ? C33 C34 C41 116.96(18) . . ? C33 C34 C35 104.04(18) . . ? C41 C34 C35 115.8(2) . . ? C33 C34 C38 97.86(16) . . ? C41 C34 C38 118.3(2) . . ? C35 C34 C38 101.01(18) . . ? C34 C35 C36 104.68(19) . . ? C34 C35 H35A 110.8 . . ? C36 C35 H35A 110.8 . . ? C34 C35 H35B 110.8 . . ? C36 C35 H35B 110.8 . . ? H35A C35 H35B 108.9 . . ? C37 C36 C35 103.1(2) . . ? C37 C36 H36A 111.1 . . ? C35 C36 H36A 111.1 . . ? C37 C36 H36B 111.1 . . ? C35 C36 H36B 111.1 . . ? H36A C36 H36B 109.1 . . ? C32 C37 C36 105.85(19) . . ? C32 C37 C38 99.28(17) . . ? C36 C37 C38 101.96(19) . . ? C32 C37 H37 115.9 . . ? C36 C37 H37 115.9 . . ? C38 C37 H37 115.9 . . ? C39 C38 C40 109.0(2) . . ? C39 C38 C37 113.5(2) . . ? C40 C38 C37 113.4(2) . . ? C39 C38 C34 113.6(2) . . ? C40 C38 C34 112.7(2) . . ? C37 C38 C34 94.17(17) . . ? C38 C39 H39A 109.5 . . ? C38 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? C38 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? C38 C40 H40A 109.5 . . ? C38 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C38 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C34 C41 H41A 109.5 . . ? C34 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C34 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? C2 N1 C3 104.0(2) . . ? C2 N2 C4 106.34(19) . . ? C2 N2 C5 127.20(19) . . ? C4 N2 C5 126.4(2) . . ? C13 N11 N12 102.14(16) . . ? N11 N12 C11 113.18(15) . . ? N11 N12 C1 118.94(15) . . ? C11 N12 C1 127.78(17) . . ? C33 N31 N32 102.55(15) . . ? C31 N32 N31 112.91(15) . . ? C31 N32 C1 127.83(16) . . ? N31 N32 C1 117.17(15) . . ? #------------------------------------------------------------------ data_ambu01 _database_code_depnum_ccdc_archive 'CCDC 807803' #TrackingRef '- compounds_3_4_6.cif' _audit_creation_date 2011-04-07T21:28:29-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C28 H38 N4 O S' _chemical_formula_weight 478.68 _chemical_absolute_configuration rmad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 26.0261(6) _cell_length_b 7.9220(2) _cell_length_c 16.4224(5) _cell_angle_alpha 90 _cell_angle_beta 127.099(4) _cell_angle_gamma 90 _cell_volume 2700.61(19) _cell_formula_units_Z 4 _cell_measurement_temperature 220(2) _cell_measurement_reflns_used 3804 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 22.97 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.177 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.146 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker-AXS, 2008' _exptl_absorpt_correction_T_min 0.6978 _exptl_absorpt_correction_T_max 0.7455 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 220(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0433 _diffrn_reflns_av_unetI/netI 0.0499 _diffrn_reflns_number 16574 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 27.44 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _reflns_number_total 6038 _reflns_number_gt 4927 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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. The thienyl moiety of the ligand is disordered. The main fraction shows an occupancy of 0.72, the second fraction is rotated by 180 degrees and shows an occupancy of 0.28. 91 restrains (SIMU) have been applied to perform an anisotropic refinement of this thienly moiety. ; _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^)+(0.0553P)^2^+0.0743P] 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_number_reflns 6038 _refine_ls_number_parameters 367 _refine_ls_number_restraints 91 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1091 _refine_ls_wR_factor_gt 0.101 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.03 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(8) _refine_diff_density_max 0.196 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.34176(9) 0.1185(2) 0.31634(14) 0.0273(4) Uani 1 1 d . A . H1 H 0.3836 0.1295 0.3835 0.033 Uiso 1 1 calc R . . C2 C 0.32959(9) -0.0671(2) 0.29306(14) 0.0298(4) Uani 1 1 d . . . C3A C 0.3486(3) -0.1693(11) 0.2506(6) 0.0508(16) Uani 0.718(3) 1 d PDU A 1 H3A H 0.3694 -0.129 0.2243 0.061 Uiso 0.718(3) 1 calc PR A 1 C4A C 0.3348(4) -0.3412(10) 0.2486(6) 0.0460(13) Uani 0.718(3) 1 d PDU A 1 H4A H 0.3465 -0.4257 0.2234 0.055 Uiso 0.718(3) 1 calc PR A 1 C5A C 0.3025(4) -0.3692(7) 0.2877(8) 0.0445(11) Uani 0.718(3) 1 d PDU A 1 H5A H 0.2888 -0.4748 0.2924 0.053 Uiso 0.718(3) 1 calc PR A 1 S1A S 0.28971(7) -0.18372(14) 0.32786(11) 0.0515(4) Uani 0.718(3) 1 d PDU A 1 C3B C 0.2967(7) -0.1639(18) 0.3052(11) 0.056(3) Uani 0.282(3) 1 d PDU A 2 H3B H 0.2699 -0.1246 0.3208 0.067 Uiso 0.282(3) 1 calc PR A 2 C4B C 0.3032(13) -0.334(2) 0.294(2) 0.056(3) Uani 0.282(3) 1 d PDU A 2 H4B H 0.2836 -0.4194 0.3048 0.067 Uiso 0.282(3) 1 calc PR A 2 C5B C 0.3405(12) -0.362(2) 0.2645(19) 0.052(4) Uani 0.282(3) 1 d PDU A 2 H5B H 0.3495 -0.4671 0.251 0.062 Uiso 0.282(3) 1 calc PR A 2 S1B S 0.3697(2) -0.1726(6) 0.2555(5) 0.0530(11) Uani 0.282(3) 1 d PDU A 2 C13 C 0.20240(9) 0.2500(2) 0.28176(13) 0.0293(4) Uani 1 1 d . . . C12 C 0.24538(9) 0.2822(2) 0.38691(13) 0.0320(4) Uani 1 1 d . . . C11 C 0.30449(9) 0.2456(2) 0.41243(13) 0.0312(4) Uani 1 1 d . A . H11 H 0.3439 0.2534 0.4768 0.037 Uiso 1 1 calc R . . C17 C 0.20517(9) 0.3525(3) 0.41689(15) 0.0386(5) Uani 1 1 d . . . H17 H 0.2242 0.3458 0.4896 0.046 Uiso 1 1 calc R . . C16 C 0.18524(11) 0.5310(3) 0.36898(17) 0.0476(5) Uani 1 1 d . . . H16A H 0.1634 0.5924 0.3912 0.057 Uiso 1 1 calc R . . H16B H 0.2224 0.5954 0.3868 0.057 Uiso 1 1 calc R . . C15 C 0.13933(10) 0.4952(3) 0.25346(16) 0.0439(5) Uani 1 1 d . . . H15A H 0.1562 0.5421 0.2194 0.053 Uiso 1 1 calc R . . H15B H 0.0971 0.5431 0.2233 0.053 Uiso 1 1 calc R . . C14 C 0.13562(9) 0.2995(3) 0.24485(14) 0.0352(4) Uani 1 1 d . . . C21 C 0.07914(10) 0.2308(3) 0.14360(15) 0.0509(6) Uani 1 1 d . . . H21A H 0.0398 0.2722 0.1293 0.076 Uiso 1 1 calc R . . H21B H 0.0795 0.1097 0.1463 0.076 Uiso 1 1 calc R . . H21C H 0.0821 0.2667 0.0908 0.076 Uiso 1 1 calc R . . C18 C 0.14159(10) 0.2510(3) 0.34311(15) 0.0409(5) Uani 1 1 d . . . C20 C 0.08573(11) 0.3149(4) 0.34302(18) 0.0599(6) Uani 1 1 d . . . H20A H 0.08 0.4338 0.3291 0.09 Uiso 1 1 calc R . . H20B H 0.0954 0.2942 0.4086 0.09 Uiso 1 1 calc R . . H20C H 0.0469 0.2565 0.2913 0.09 Uiso 1 1 calc R . . C19 C 0.14938(12) 0.0619(3) 0.3649(2) 0.0588(7) Uani 1 1 d . . . H19A H 0.1843 0.02 0.3657 0.088 Uiso 1 1 calc R . . H19B H 0.1103 0.0049 0.3127 0.088 Uiso 1 1 calc R . . H19C H 0.1584 0.0418 0.4301 0.088 Uiso 1 1 calc R . . C33 C 0.39364(9) 0.2637(2) 0.17798(13) 0.0305(4) Uani 1 1 d . . . C32 C 0.32813(9) 0.2843(2) 0.10019(14) 0.0330(4) Uani 1 1 d . . . C31 C 0.29868(9) 0.2438(2) 0.14339(13) 0.0333(4) Uani 1 1 d . A . H31 H 0.2546 0.2418 0.1112 0.04 Uiso 1 1 calc R . . C37 C 0.32263(10) 0.3503(3) 0.00895(15) 0.0433(5) Uani 1 1 d . . . H37 H 0.2807 0.3356 -0.0575 0.052 Uiso 1 1 calc R . . C36 C 0.34907(11) 0.5317(3) 0.03647(16) 0.0451(5) Uani 1 1 d . . . H36A H 0.3281 0.5976 0.0586 0.054 Uiso 1 1 calc R . . H36B H 0.3431 0.5876 -0.0213 0.054 Uiso 1 1 calc R . . C35 C 0.42156(10) 0.5070(3) 0.12479(16) 0.0421(5) Uani 1 1 d . . . H35A H 0.4481 0.5544 0.1072 0.051 Uiso 1 1 calc R . . H35B H 0.4329 0.5602 0.1868 0.051 Uiso 1 1 calc R . . C34 C 0.43047(9) 0.3131(3) 0.13838(15) 0.0381(4) Uani 1 1 d . . . C41 C 0.49906(11) 0.2509(4) 0.1969(2) 0.0628(7) Uani 1 1 d . . . H41A H 0.5174 0.29 0.1642 0.094 Uiso 1 1 calc R . . H41B H 0.4995 0.1298 0.1983 0.094 Uiso 1 1 calc R . . H41C H 0.5239 0.2935 0.2655 0.094 Uiso 1 1 calc R . . C38 C 0.38035(12) 0.2531(3) 0.02465(17) 0.0473(5) Uani 1 1 d . . . C39 C 0.37028(17) 0.0614(3) 0.0124(2) 0.0729(9) Uani 1 1 d . . . H39A H 0.3605 0.0209 0.0567 0.109 Uiso 1 1 calc R . . H39B H 0.4088 0.0078 0.0299 0.109 Uiso 1 1 calc R . . H39C H 0.3352 0.0354 -0.0571 0.109 Uiso 1 1 calc R . . C40 C 0.39589(14) 0.3149(4) -0.04751(19) 0.0662(7) Uani 1 1 d . . . H40A H 0.4023 0.4349 -0.0408 0.099 Uiso 1 1 calc R . . H40B H 0.3607 0.2877 -0.1167 0.099 Uiso 1 1 calc R . . H40C H 0.4344 0.2604 -0.0298 0.099 Uiso 1 1 calc R . . N12 N 0.29423(7) 0.19495(19) 0.32369(11) 0.0285(3) Uani 1 1 d . . . N11 N 0.22997(7) 0.1949(2) 0.24132(11) 0.0309(3) Uani 1 1 d . A . N32 N 0.34668(7) 0.20654(18) 0.24363(10) 0.0263(3) Uani 1 1 d . . . N31 N 0.40685(7) 0.21638(19) 0.26604(11) 0.0300(3) Uani 1 1 d . A . O70 O 0.53711(16) 0.2743(5) 0.4484(3) 0.0679(10) Uani 0.5 1 d P B 1 H70 H 0.5018 0.2364 0.4016 0.102 Uiso 0.5 1 calc PR B 1 C70 C 0.5298(3) 0.4350(10) 0.4712(6) 0.097(2) Uani 0.5 1 d P B 1 H70A H 0.4997 0.4957 0.4091 0.145 Uiso 0.5 1 calc PR B 1 H70B H 0.5706 0.4919 0.5096 0.145 Uiso 0.5 1 calc PR B 1 H70C H 0.5139 0.4298 0.5109 0.145 Uiso 0.5 1 calc PR B 1 O80 O 0.53081(18) 0.0892(6) 0.4461(3) 0.0765(12) Uani 0.5 1 d P C 2 H80 H 0.5083 0.1638 0.4444 0.115 Uiso 0.5 1 calc PR C 2 C80 C 0.5126(3) -0.0712(11) 0.4627(5) 0.099(2) Uani 0.5 1 d P C 2 H80A H 0.5504 -0.13 0.5169 0.149 Uiso 0.5 1 calc PR C 2 H80B H 0.4909 -0.1371 0.4013 0.149 Uiso 0.5 1 calc PR C 2 H80C H 0.4842 -0.0534 0.4809 0.149 Uiso 0.5 1 calc PR C 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0253(9) 0.0262(9) 0.0271(9) 0.0022(7) 0.0141(8) 0.0031(7) C2 0.0312(10) 0.0268(9) 0.0320(10) 0.0022(7) 0.0193(9) 0.0018(7) C3A 0.062(4) 0.039(2) 0.062(2) 0.0031(17) 0.043(3) -0.001(3) C4A 0.067(2) 0.028(2) 0.058(3) -0.0034(19) 0.046(2) 0.0013(19) C5A 0.0614(19) 0.017(2) 0.068(2) 0.001(2) 0.0457(18) -0.001(2) S1A 0.0758(6) 0.0271(4) 0.0855(8) 0.0025(5) 0.0664(6) -0.0024(4) C3B 0.076(5) 0.039(5) 0.076(5) 0.006(4) 0.058(4) 0.000(4) C4B 0.069(4) 0.027(5) 0.073(4) 0.002(4) 0.044(3) 0.000(4) C5B 0.068(4) 0.017(4) 0.067(5) 0.000(4) 0.039(4) -0.002(4) S1B 0.081(3) 0.0232(11) 0.0802(19) -0.0073(11) 0.062(2) -0.0011(18) C13 0.0305(9) 0.0270(8) 0.0305(9) 0.0009(7) 0.0185(8) 0.0012(7) C12 0.0350(10) 0.0308(10) 0.0322(10) -0.0008(7) 0.0214(9) -0.0015(8) C11 0.0339(10) 0.0318(9) 0.0258(8) -0.0013(7) 0.0169(8) -0.0031(8) C17 0.0409(11) 0.0499(13) 0.0350(10) -0.0005(9) 0.0281(9) 0.0013(9) C16 0.0620(14) 0.0408(12) 0.0608(14) -0.0038(11) 0.0480(13) 0.0064(11) C15 0.0496(12) 0.0409(11) 0.0550(13) 0.0122(10) 0.0388(11) 0.0154(10) C14 0.0306(10) 0.0430(11) 0.0321(10) 0.0031(8) 0.0190(9) 0.0063(9) C21 0.0307(11) 0.0734(16) 0.0404(11) -0.0033(11) 0.0171(10) 0.0039(10) C18 0.0356(11) 0.0507(12) 0.0395(11) 0.0062(9) 0.0244(9) 0.0014(9) C20 0.0466(13) 0.0929(19) 0.0572(14) 0.0109(14) 0.0402(12) 0.0043(14) C19 0.0509(14) 0.0547(15) 0.0666(16) 0.0157(12) 0.0332(13) -0.0072(11) C33 0.0282(9) 0.0275(9) 0.0338(9) 0.0016(8) 0.0178(8) 0.0020(7) C32 0.0290(10) 0.0351(11) 0.0312(9) -0.0020(8) 0.0161(8) -0.0011(7) C31 0.0230(9) 0.0387(10) 0.0293(9) -0.0025(8) 0.0111(8) -0.0031(8) C37 0.0386(11) 0.0564(14) 0.0308(10) 0.0032(9) 0.0188(9) -0.0041(10) C36 0.0514(13) 0.0452(12) 0.0450(12) 0.0126(10) 0.0324(11) 0.0084(10) C35 0.0419(11) 0.0387(11) 0.0475(12) 0.0047(10) 0.0278(10) -0.0036(10) C34 0.0342(10) 0.0401(10) 0.0458(11) 0.0058(9) 0.0271(10) 0.0028(9) C41 0.0442(13) 0.0715(17) 0.0867(18) 0.0283(14) 0.0468(14) 0.0160(12) C38 0.0599(14) 0.0473(12) 0.0495(12) -0.0053(10) 0.0408(12) -0.0048(11) C39 0.116(3) 0.0521(15) 0.086(2) -0.0180(14) 0.080(2) -0.0140(15) C40 0.0891(19) 0.0703(16) 0.0682(17) -0.0012(15) 0.0627(16) -0.0026(16) N12 0.0253(7) 0.0276(8) 0.0284(7) -0.0022(6) 0.0140(6) 0.0012(6) N11 0.0255(8) 0.0321(8) 0.0299(8) -0.0023(6) 0.0140(7) 0.0015(6) N32 0.0231(7) 0.0245(7) 0.0268(7) 0.0013(6) 0.0126(6) -0.0004(6) N31 0.0242(7) 0.0261(8) 0.0375(8) 0.0033(6) 0.0174(7) 0.0015(6) O70 0.0393(18) 0.078(3) 0.051(2) 0.0003(19) 0.0084(17) -0.0054(17) C70 0.059(4) 0.095(5) 0.089(5) -0.004(4) 0.020(4) -0.015(4) O80 0.052(2) 0.096(3) 0.058(2) 0.002(2) 0.021(2) 0.015(2) C80 0.065(4) 0.124(7) 0.078(5) -0.004(4) 0.027(4) 0.017(4) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N12 1.446(2) . ? C1 N32 1.454(2) . ? C1 C2 1.504(2) . ? C2 C3B 1.252(13) . ? C2 C3A 1.342(7) . ? C2 S1B 1.717(4) . ? C2 S1A 1.724(2) . ? C3A C4A 1.404(10) . ? C4A C5A 1.349(6) . ? C5A S1A 1.722(6) . ? C3B C4B 1.384(17) . ? C4B C5B 1.335(15) . ? C5B S1B 1.725(18) . ? C13 N11 1.312(2) . ? C13 C12 1.403(2) . ? C13 C14 1.507(2) . ? C12 C11 1.359(3) . ? C12 C17 1.507(2) . ? C11 N12 1.374(2) . ? C17 C16 1.547(3) . ? C17 C18 1.560(3) . ? C16 C15 1.540(3) . ? C15 C14 1.555(3) . ? C14 C21 1.508(3) . ? C14 C18 1.573(3) . ? C18 C19 1.525(3) . ? C18 C20 1.538(3) . ? C33 N31 1.323(2) . ? C33 C32 1.392(2) . ? C33 C34 1.499(2) . ? C32 C31 1.360(3) . ? C32 C37 1.510(3) . ? C31 N32 1.370(2) . ? C37 C36 1.539(3) . ? C37 C38 1.565(3) . ? C36 C35 1.549(3) . ? C35 C34 1.549(3) . ? C34 C41 1.511(3) . ? C34 C38 1.574(3) . ? C38 C39 1.534(3) . ? C38 C40 1.545(3) . ? N12 N11 1.3775(19) . ? N32 N31 1.378(2) . ? O70 C70 1.373(8) . ? O80 C80 1.439(8) . ? 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 N12 C1 N32 111.80(14) . . ? N12 C1 C2 111.77(15) . . ? N32 C1 C2 111.70(15) . . ? C3B C2 C1 128.2(7) . . ? C3A C2 C1 129.4(4) . . ? C3B C2 S1B 112.5(7) . . ? C1 C2 S1B 119.1(2) . . ? C3A C2 S1A 109.4(3) . . ? C1 C2 S1A 121.08(14) . . ? C2 C3A C4A 115.4(6) . . ? C5A C4A C3A 111.8(6) . . ? C4A C5A S1A 111.2(6) . . ? C5A S1A C2 92.1(3) . . ? C2 C3B C4B 115.0(13) . . ? C5B C4B C3B 112.6(19) . . ? C4B C5B S1B 110.0(17) . . ? C2 S1B C5B 89.8(8) . . ? N11 C13 C12 114.20(16) . . ? N11 C13 C14 137.15(16) . . ? C12 C13 C14 108.54(15) . . ? C11 C12 C13 104.76(15) . . ? C11 C12 C17 149.09(17) . . ? C13 C12 C17 105.90(16) . . ? C12 C11 N12 105.99(15) . . ? C12 C17 C16 104.93(15) . . ? C12 C17 C18 100.13(15) . . ? C16 C17 C18 101.71(17) . . ? C15 C16 C17 103.35(17) . . ? C16 C15 C14 104.79(16) . . ? C13 C14 C21 118.08(16) . . ? C13 C14 C15 103.26(16) . . ? C21 C14 C15 115.21(17) . . ? C13 C14 C18 98.50(14) . . ? C21 C14 C18 118.07(17) . . ? C15 C14 C18 100.83(15) . . ? C19 C18 C20 108.4(2) . . ? C19 C18 C17 113.31(18) . . ? C20 C18 C17 112.96(18) . . ? C19 C18 C14 113.42(18) . . ? C20 C18 C14 114.22(17) . . ? C17 C18 C14 94.18(15) . . ? N31 C33 C32 113.77(16) . . ? N31 C33 C34 137.37(16) . . ? C32 C33 C34 108.73(15) . . ? C31 C32 C33 104.92(15) . . ? C31 C32 C37 148.57(18) . . ? C33 C32 C37 106.36(16) . . ? C32 C31 N32 106.57(15) . . ? C32 C37 C36 105.91(17) . . ? C32 C37 C38 99.15(16) . . ? C36 C37 C38 101.32(17) . . ? C37 C36 C35 103.48(17) . . ? C34 C35 C36 104.61(17) . . ? C33 C34 C41 117.26(17) . . ? C33 C34 C35 103.99(16) . . ? C41 C34 C35 115.57(18) . . ? C33 C34 C38 98.45(15) . . ? C41 C34 C38 118.19(19) . . ? C35 C34 C38 100.57(16) . . ? C39 C38 C40 108.4(2) . . ? C39 C38 C37 113.2(2) . . ? C40 C38 C37 112.8(2) . . ? C39 C38 C34 114.1(2) . . ? C40 C38 C34 113.69(19) . . ? C37 C38 C34 94.20(15) . . ? C11 N12 N11 112.70(14) . . ? C11 N12 C1 125.61(15) . . ? N11 N12 C1 120.72(14) . . ? C13 N11 N12 102.34(13) . . ? C31 N32 N31 112.00(14) . . ? C31 N32 C1 128.46(14) . . ? N31 N32 C1 117.19(14) . . ? C33 N31 N32 102.71(14) . . ? #-------------------------------------------------------- data_sbbu01 _database_code_depnum_ccdc_archive 'CCDC 807804' #TrackingRef '- compounds_3_4_6.cif' _audit_creation_date 2009-11-22T22:11:03-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C27 H40 N6' _chemical_formula_sum 'C27 H40 N6' _chemical_formula_weight 448.65 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration rm #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) _symmetry_space_group_name_Hall 'P 2yb' _symmetry_Int_Tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.8408(3) _cell_length_b 11.2369(4) _cell_length_c 27.0450(9) _cell_angle_alpha 90 _cell_angle_beta 93.068(2) _cell_angle_gamma 90 _cell_volume 2682.89(16) _cell_formula_units_Z 4 _cell_measurement_temperature 230(2) _cell_measurement_reflns_used 2723 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 20.82 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.111 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.068 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS, Bruker-AXS, 2008' _exptl_absorpt_correction_T_min 0.6982 _exptl_absorpt_correction_T_max 0.7455 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 230(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number 0 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_unetI/netI 0.0516 _diffrn_reflns_number 18702 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.51 _diffrn_reflns_theta_max 25.35 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 5177 _reflns_number_gt 3902 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0890P)^2^+0.1669P] 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_number_reflns 5177 _refine_ls_number_parameters 622 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1485 _refine_ls_wR_factor_gt 0.1328 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_diff_density_max 0.395 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.039 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.0187(4) 0.2261(4) 0.29382(13) 0.0403(9) Uani 1 1 d . . . H1 H 0.9189 0.1981 0.3028 0.048 Uiso 1 1 calc R . . C2 C 0.9962(4) 0.3422(4) 0.26712(13) 0.0368(9) Uani 1 1 d . . . C3 C 0.9884(4) 0.4804(4) 0.21353(14) 0.0418(9) Uani 1 1 d . . . H3 H 1.0022 0.522 0.1844 0.05 Uiso 1 1 calc R . . C4 C 0.9171(4) 0.5246(4) 0.25248(14) 0.0419(9) Uani 1 1 d . . . H4 H 0.8743 0.5997 0.2554 0.05 Uiso 1 1 calc R . . C5 C 0.8576(5) 0.4428(5) 0.33542(14) 0.0557(12) Uani 1 1 d . . . H5A H 0.8109 0.3684 0.3431 0.083 Uiso 1 1 calc R . . H5B H 0.7832 0.505 0.335 0.083 Uiso 1 1 calc R . . H5C H 0.9369 0.4602 0.36 0.083 Uiso 1 1 calc R . . C11 C 1.2418(5) 0.3023(4) 0.34720(14) 0.0471(10) Uani 1 1 d . . . H11 H 1.2944 0.3429 0.3236 0.056 Uiso 1 1 calc R . . C12 C 1.2835(5) 0.2916(5) 0.39608(14) 0.0532(12) Uani 1 1 d . . . C13 C 1.1681(5) 0.2268(4) 0.41603(14) 0.0496(11) Uani 1 1 d . . . C14 C 1.1584(6) 0.1992(4) 0.47036(15) 0.0556(12) Uani 1 1 d . . . H14 H 1.0981 0.262 0.485 0.067 Uiso 1 1 calc R . . C15 C 1.3212(6) 0.2078(7) 0.49384(17) 0.0800(18) Uani 1 1 d . . . H15A H 1.3807 0.1416 0.4826 0.096 Uiso 1 1 calc R . . H15B H 1.3182 0.2024 0.5296 0.096 Uiso 1 1 calc R . . C16 C 1.3977(8) 0.3262(8) 0.47993(19) 0.100(2) Uani 1 1 d . . . H16A H 1.3346 0.3922 0.4892 0.12 Uiso 1 1 calc R . . H16B H 1.4944 0.3332 0.4984 0.12 Uiso 1 1 calc R . . C17 C 1.4226(6) 0.3333(6) 0.42533(16) 0.0752(17) Uani 1 1 d . . . H17 H 1.4329 0.4181 0.4178 0.09 Uiso 1 1 calc R . . C18 C 1.5623(7) 0.2758(11) 0.4097(2) 0.138(4) Uani 1 1 d . . . H18A H 1.6477 0.3056 0.4293 0.207 Uiso 1 1 calc R . . H18B H 1.5753 0.2931 0.3754 0.207 Uiso 1 1 calc R . . H18C H 1.5549 0.1913 0.4141 0.207 Uiso 1 1 calc R . . C19 C 1.0797(5) 0.0782(4) 0.47996(15) 0.0512(11) Uani 1 1 d . . . H19 H 0.9806 0.0795 0.4619 0.061 Uiso 1 1 calc R . . C20 C 1.1670(8) -0.0244(5) 0.4605(2) 0.0872(18) Uani 1 1 d . . . H20A H 1.1832 -0.0118 0.4261 0.131 Uiso 1 1 calc R . . H20B H 1.1107 -0.0966 0.4643 0.131 Uiso 1 1 calc R . . H20C H 1.2629 -0.0306 0.4787 0.131 Uiso 1 1 calc R . . C21 C 1.0525(8) 0.0616(7) 0.5338(2) 0.095(2) Uani 1 1 d . . . H21A H 0.9984 0.1291 0.5456 0.143 Uiso 1 1 calc R . . H21B H 1.1479 0.0544 0.5523 0.143 Uiso 1 1 calc R . . H21C H 0.9939 -0.0092 0.538 0.143 Uiso 1 1 calc R . . C31 C 1.2197(4) 0.1298(4) 0.24424(15) 0.0447(9) Uani 1 1 d . . . H31 H 1.2989 0.1832 0.2502 0.054 Uiso 1 1 calc R . . C32 C 1.2226(4) 0.0305(4) 0.21543(15) 0.0425(9) Uani 1 1 d . . . C33 C 1.0780(5) -0.0176(4) 0.21696(14) 0.0423(9) Uani 1 1 d . . . C34 C 1.0239(5) -0.1310(4) 0.19167(17) 0.0520(11) Uani 1 1 d . . . H34 H 1.0156 -0.1917 0.2174 0.062 Uiso 1 1 calc R . . C35 C 1.1479(6) -0.1725(5) 0.1575(2) 0.0775(16) Uani 1 1 d . . . H35A H 1.1332 -0.2564 0.1503 0.093 Uiso 1 1 calc R . . H35B H 1.1361 -0.1295 0.1264 0.093 Uiso 1 1 calc R . . C36 C 1.3093(6) -0.1540(5) 0.1793(2) 0.0767(16) Uani 1 1 d . . . H36A H 1.3209 -0.1949 0.2109 0.092 Uiso 1 1 calc R . . H36B H 1.3802 -0.189 0.1573 0.092 Uiso 1 1 calc R . . C37 C 1.3476(5) -0.0237(4) 0.18691(17) 0.0559(11) Uani 1 1 d . . . H37 H 1.4407 -0.0199 0.2082 0.067 Uiso 1 1 calc R . . C38 C 1.3770(6) 0.0430(5) 0.1399(2) 0.0751(16) Uani 1 1 d . . . H38A H 1.4582 0.0053 0.1236 0.113 Uiso 1 1 calc R . . H38B H 1.4045 0.1237 0.1478 0.113 Uiso 1 1 calc R . . H38C H 1.2871 0.0424 0.1183 0.113 Uiso 1 1 calc R . . C39 C 0.8664(6) -0.1157(4) 0.16608(18) 0.0571(12) Uani 1 1 d . . . H39 H 0.7992 -0.0876 0.1913 0.069 Uiso 1 1 calc R . . C40 C 0.8613(6) -0.0234(5) 0.12517(19) 0.0715(14) Uani 1 1 d . . . H40A H 0.76 -0.0179 0.1107 0.107 Uiso 1 1 calc R . . H40B H 0.929 -0.0464 0.1003 0.107 Uiso 1 1 calc R . . H40C H 0.8916 0.0524 0.1387 0.107 Uiso 1 1 calc R . . C41 C 0.8028(8) -0.2348(6) 0.1469(3) 0.0919(19) Uani 1 1 d . . . H41A H 0.8057 -0.2917 0.1734 0.138 Uiso 1 1 calc R . . H41B H 0.8629 -0.2634 0.1208 0.138 Uiso 1 1 calc R . . H41C H 0.7 -0.2242 0.1344 0.138 Uiso 1 1 calc R . . C51 C 0.5340(4) 0.5074(3) 0.20745(12) 0.0334(8) Uani 1 1 d . . . H51 H 0.6283 0.5436 0.1972 0.04 Uiso 1 1 calc R . . C52 C 0.5711(4) 0.3844(3) 0.22464(13) 0.0344(8) Uani 1 1 d . . . C53 C 0.5998(5) 0.2270(4) 0.26827(18) 0.0508(11) Uani 1 1 d . . . H53 H 0.5951 0.1735 0.2944 0.061 Uiso 1 1 calc R . . C54 C 0.6692(5) 0.2056(4) 0.22591(17) 0.0500(11) Uani 1 1 d . . . H54 H 0.7189 0.1362 0.2174 0.06 Uiso 1 1 calc R . . C55 C 0.7042(6) 0.3252(5) 0.14856(16) 0.0614(13) Uani 1 1 d . . . H55A H 0.625 0.3044 0.1244 0.092 Uiso 1 1 calc R . . H55B H 0.7912 0.2761 0.144 0.092 Uiso 1 1 calc R . . H55C H 0.731 0.4073 0.1446 0.092 Uiso 1 1 calc R . . C61 C 0.3461(4) 0.5729(4) 0.26952(13) 0.0363(8) Uani 1 1 d . . . H61 H 0.2593 0.5336 0.2574 0.044 Uiso 1 1 calc R . . C62 C 0.3630(4) 0.6363(4) 0.31274(13) 0.0363(8) Uani 1 1 d . . . C63 C 0.5145(4) 0.6749(3) 0.31502(12) 0.0314(8) Uani 1 1 d . . . C64 C 0.5869(4) 0.7474(3) 0.35635(13) 0.0365(8) Uani 1 1 d D . . H64 H 0.6414 0.6916 0.3787 0.044 Uiso 1 1 calc R . . C65 C 0.4604(5) 0.8022(4) 0.38535(14) 0.0462(10) Uani 1 1 d D . . H65A H 0.5035 0.8364 0.4159 0.055 Uiso 1 1 calc R . . H65B H 0.4124 0.8658 0.366 0.055 Uiso 1 1 calc R . . C66 C 0.3416(5) 0.7101(5) 0.39750(15) 0.0559(12) Uani 1 1 d D . . H66A H 0.2719 0.7452 0.4198 0.067 Uiso 1 1 calc R . . H66B H 0.3913 0.6435 0.4144 0.067 Uiso 1 1 calc R . . C67 C 0.2522(5) 0.6643(4) 0.35134(15) 0.0515(11) Uani 1 1 d D . . H67 H 0.2013 0.5903 0.36 0.062 Uiso 1 1 calc R . . C68 C 0.1341(6) 0.7511(6) 0.3325(2) 0.0814(19) Uani 1 1 d . . . H68A H 0.0648 0.7665 0.3579 0.122 Uiso 1 1 calc R . . H68B H 0.0798 0.7184 0.3039 0.122 Uiso 1 1 calc R . . H68C H 0.1821 0.8241 0.3235 0.122 Uiso 1 1 calc R . . C69 C 0.7049(4) 0.8372(4) 0.33882(14) 0.0426(9) Uani 1 1 d . . . H69 H 0.7823 0.7911 0.3226 0.051 Uiso 1 1 calc R . . C70 C 0.7847(6) 0.9022(5) 0.38199(19) 0.0699(15) Uani 1 1 d . . . H70A H 0.8279 0.8454 0.4052 0.105 Uiso 1 1 calc R . . H70B H 0.7131 0.9511 0.3981 0.105 Uiso 1 1 calc R . . H70C H 0.8636 0.9514 0.37 0.105 Uiso 1 1 calc R . . C71 C 0.6371(6) 0.9229(5) 0.3005(2) 0.0666(14) Uani 1 1 d . . . H71A H 0.5896 0.8789 0.2735 0.1 Uiso 1 1 calc R . . H71B H 0.7157 0.9723 0.2884 0.1 Uiso 1 1 calc R . . H71C H 0.563 0.972 0.3154 0.1 Uiso 1 1 calc R . . C81 C 0.3098(4) 0.4331(4) 0.15416(13) 0.0398(9) Uani 1 1 d . . . H81 H 0.2778 0.3706 0.1736 0.048 Uiso 1 1 calc R . . C82 C 0.2458(5) 0.4692(4) 0.10983(13) 0.0466(10) Uani 1 1 d . . . C83 C 0.3337(5) 0.5649(4) 0.09529(14) 0.0477(10) Uani 1 1 d . B . C84 C 0.3090(7) 0.6340(5) 0.04798(16) 0.0731(15) Uani 1 1 d D . . H84 H 0.2753 0.7104 0.061 0.088 Uiso 1 1 calc R A 1 C85 C 0.1658(12) 0.5906(11) 0.0233(3) 0.174(5) Uani 1 1 d D B . H85A H 0.09 0.6504 0.0297 0.209 Uiso 1 1 calc R . . H85B H 0.1805 0.5936 -0.0119 0.209 Uiso 1 1 calc R . . C86 C 0.0997(10) 0.4837(12) 0.0317(3) 0.155(5) Uani 1 1 d D . . H86A H 0.1399 0.4283 0.0083 0.186 Uiso 1 1 calc R B . H86B H -0.0071 0.4929 0.0223 0.186 Uiso 1 1 calc R . . C87 C 0.1076(5) 0.4223(6) 0.08052(16) 0.0690(16) Uani 1 1 d D B . H87 H 0.0181 0.4459 0.098 0.083 Uiso 1 1 calc R . . C88 C 0.1077(9) 0.2882(9) 0.0770(3) 0.143(4) Uani 1 1 d . . . H88A H 0.0188 0.2623 0.058 0.214 Uiso 1 1 calc R B . H88B H 0.108 0.2547 0.1096 0.214 Uiso 1 1 calc R . . H88C H 0.1964 0.2624 0.061 0.214 Uiso 1 1 calc R . . C89 C 0.450(3) 0.672(2) 0.0237(7) 0.105(6) Uani 0.5 1 d PD B 1 H89 H 0.5132 0.714 0.049 0.126 Uiso 0.5 1 calc PR B 1 C90 C 0.538(5) 0.562(3) 0.0094(12) 0.191(18) Uani 0.5 1 d PD B 1 H90A H 0.5579 0.5132 0.0381 0.286 Uiso 0.5 1 calc PR B 1 H90B H 0.6326 0.5859 -0.0037 0.286 Uiso 0.5 1 calc PR B 1 H90C H 0.48 0.518 -0.0153 0.286 Uiso 0.5 1 calc PR B 1 C91 C 0.422(4) 0.760(2) -0.0191(7) 0.185(14) Uani 0.5 1 d PD B 1 H91A H 0.3617 0.8257 -0.0083 0.278 Uiso 0.5 1 calc PR B 1 H91B H 0.3688 0.7209 -0.0463 0.278 Uiso 0.5 1 calc PR B 1 H91C H 0.5168 0.7899 -0.0295 0.278 Uiso 0.5 1 calc PR B 1 C92 C 0.430(2) 0.6070(15) 0.0100(6) 0.074(5) Uani 0.5 1 d PD B 2 H92 H 0.4088 0.5264 -0.0023 0.088 Uiso 0.5 1 calc PR B 2 C93 C 0.593(2) 0.608(3) 0.0289(7) 0.117(9) Uani 0.5 1 d PD B 2 H93A H 0.6059 0.557 0.0573 0.175 Uiso 0.5 1 calc PR B 2 H93B H 0.6226 0.6877 0.038 0.175 Uiso 0.5 1 calc PR B 2 H93C H 0.6559 0.58 0.0033 0.175 Uiso 0.5 1 calc PR B 2 C94 C 0.401(3) 0.6903(16) -0.0338(6) 0.105(6) Uani 0.5 1 d PD B 2 H94A H 0.2945 0.6907 -0.0433 0.157 Uiso 0.5 1 calc PR B 2 H94B H 0.4568 0.6633 -0.0611 0.157 Uiso 0.5 1 calc PR B 2 H94C H 0.4326 0.7693 -0.0247 0.157 Uiso 0.5 1 calc PR B 2 N1 N 1.0380(4) 0.3663(3) 0.22234(11) 0.0399(8) Uani 1 1 d . . . N2 N 0.9216(3) 0.4347(3) 0.28673(11) 0.0401(8) Uani 1 1 d . . . N11 N 1.0603(4) 0.1963(4) 0.38184(12) 0.0524(9) Uani 1 1 d . . . N12 N 1.1102(4) 0.2432(3) 0.33937(10) 0.0431(8) Uani 1 1 d . . . N31 N 0.9907(4) 0.0455(3) 0.24593(12) 0.0421(8) Uani 1 1 d . . . N32 N 1.0816(4) 0.1362(3) 0.26242(11) 0.0396(7) Uani 1 1 d . . . N51 N 0.5369(4) 0.3391(3) 0.26747(12) 0.0418(8) Uani 1 1 d . . . N52 N 0.6515(4) 0.3065(3) 0.19810(12) 0.0426(8) Uani 1 1 d . . . N61 N 0.5870(3) 0.6391(3) 0.27569(10) 0.0332(7) Uani 1 1 d . . . N62 N 0.4812(3) 0.5787(3) 0.24771(10) 0.0316(7) Uani 1 1 d . . . N81 N 0.4462(4) 0.5889(3) 0.12861(11) 0.0450(8) Uani 1 1 d . . . N82 N 0.4290(3) 0.5059(3) 0.16444(10) 0.0349(7) Uani 1 1 d . B . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.035(2) 0.055(2) 0.0309(19) -0.0002(18) -0.0011(15) -0.009(2) C2 0.0272(18) 0.049(2) 0.0340(19) -0.0074(17) -0.0021(15) -0.0060(19) C3 0.036(2) 0.047(2) 0.042(2) 0.0029(18) -0.0007(16) 0.000(2) C4 0.031(2) 0.044(2) 0.050(2) -0.0043(19) -0.0017(17) -0.003(2) C5 0.054(3) 0.077(3) 0.037(2) -0.015(2) 0.0101(19) 0.007(3) C11 0.050(3) 0.054(3) 0.037(2) 0.0002(19) -0.0014(18) -0.016(2) C12 0.056(3) 0.069(3) 0.035(2) -0.001(2) -0.0006(19) -0.019(2) C13 0.051(2) 0.062(3) 0.036(2) 0.004(2) 0.0011(18) -0.006(2) C14 0.073(3) 0.053(3) 0.041(2) 0.002(2) 0.004(2) -0.005(3) C15 0.076(4) 0.126(5) 0.036(2) 0.010(3) -0.011(2) -0.033(4) C16 0.106(5) 0.142(6) 0.050(3) -0.002(3) -0.008(3) -0.060(5) C17 0.083(4) 0.097(4) 0.043(3) 0.003(3) -0.017(2) -0.043(4) C18 0.049(3) 0.289(13) 0.073(4) -0.028(6) -0.009(3) -0.042(6) C19 0.059(3) 0.056(3) 0.039(2) 0.003(2) 0.0056(19) -0.004(2) C20 0.118(5) 0.065(3) 0.079(4) 0.003(3) 0.005(3) 0.004(4) C21 0.122(5) 0.105(5) 0.061(3) 0.018(3) 0.023(3) -0.021(5) C31 0.032(2) 0.049(2) 0.053(2) -0.004(2) -0.0022(17) -0.001(2) C32 0.036(2) 0.042(2) 0.049(2) 0.0056(18) -0.0050(17) 0.004(2) C33 0.045(2) 0.037(2) 0.045(2) 0.0051(18) -0.0019(17) 0.000(2) C34 0.056(3) 0.036(2) 0.064(3) 0.002(2) -0.002(2) -0.001(2) C35 0.071(4) 0.054(3) 0.107(4) -0.033(3) 0.001(3) 0.008(3) C36 0.062(3) 0.053(3) 0.115(5) -0.009(3) 0.005(3) 0.016(3) C37 0.048(3) 0.054(3) 0.065(3) -0.003(2) -0.002(2) 0.015(2) C38 0.070(3) 0.079(4) 0.078(4) -0.005(3) 0.027(3) 0.013(3) C39 0.060(3) 0.052(3) 0.059(3) -0.006(2) -0.001(2) -0.011(3) C40 0.069(3) 0.078(4) 0.066(3) 0.006(3) -0.009(2) 0.002(3) C41 0.090(5) 0.070(4) 0.114(5) -0.013(3) -0.014(4) -0.024(4) C51 0.0333(19) 0.036(2) 0.0312(18) -0.0042(15) 0.0038(14) 0.0006(17) C52 0.0278(19) 0.0332(19) 0.042(2) -0.0043(16) 0.0000(16) -0.0030(17) C53 0.047(3) 0.034(2) 0.071(3) 0.007(2) -0.008(2) 0.003(2) C54 0.042(2) 0.042(2) 0.065(3) -0.012(2) -0.008(2) 0.003(2) C55 0.055(3) 0.077(3) 0.053(3) -0.025(2) 0.010(2) 0.006(3) C61 0.0290(19) 0.041(2) 0.039(2) -0.0043(17) 0.0012(15) -0.0049(18) C62 0.037(2) 0.039(2) 0.0334(19) -0.0054(16) 0.0056(15) 0.0000(19) C63 0.0299(19) 0.0300(19) 0.0342(19) -0.0006(14) 0.0002(15) 0.0004(16) C64 0.037(2) 0.038(2) 0.0335(18) -0.0017(16) -0.0061(15) 0.0022(18) C65 0.049(2) 0.051(2) 0.039(2) -0.0127(18) 0.0025(18) -0.002(2) C66 0.055(3) 0.072(3) 0.043(2) -0.012(2) 0.017(2) -0.004(3) C67 0.041(2) 0.066(3) 0.049(2) -0.017(2) 0.0153(19) -0.009(2) C68 0.039(3) 0.129(5) 0.075(3) -0.048(3) -0.003(2) 0.023(3) C69 0.036(2) 0.042(2) 0.050(2) -0.0130(18) 0.0014(17) -0.0041(19) C70 0.053(3) 0.079(4) 0.077(3) -0.035(3) 0.001(2) -0.014(3) C71 0.067(3) 0.050(3) 0.084(3) 0.014(3) 0.009(3) -0.010(3) C81 0.036(2) 0.048(2) 0.036(2) -0.0039(18) 0.0046(16) -0.002(2) C82 0.042(2) 0.066(3) 0.0316(19) -0.0107(19) -0.0010(16) 0.003(2) C83 0.066(3) 0.046(2) 0.0302(19) -0.0052(17) -0.0019(19) 0.010(2) C84 0.115(4) 0.065(3) 0.037(2) 0.000(2) -0.009(3) 0.017(4) C85 0.178(9) 0.220(12) 0.114(7) 0.094(8) -0.096(7) -0.040(9) C86 0.128(7) 0.258(14) 0.073(5) 0.033(7) -0.053(4) -0.064(8) C87 0.040(3) 0.125(5) 0.042(2) -0.014(3) -0.0054(19) 0.005(3) C88 0.120(7) 0.132(7) 0.168(8) -0.042(6) -0.064(6) -0.047(6) C89 0.124(17) 0.128(17) 0.064(10) 0.055(11) 0.010(10) -0.009(14) C90 0.21(3) 0.24(4) 0.14(3) 0.03(2) 0.09(2) 0.08(3) C91 0.28(3) 0.18(2) 0.092(14) 0.095(16) -0.049(16) -0.10(2) C92 0.112(12) 0.064(9) 0.044(7) 0.021(6) -0.001(7) -0.015(10) C93 0.113(15) 0.18(2) 0.057(10) 0.030(11) 0.029(9) -0.024(16) C94 0.141(15) 0.107(13) 0.067(9) 0.023(9) 0.024(9) -0.009(12) N1 0.0375(18) 0.050(2) 0.0320(16) 0.0008(14) 0.0051(13) -0.0031(17) N2 0.0304(17) 0.0528(19) 0.0370(16) -0.0078(16) 0.0006(13) -0.0006(17) N11 0.054(2) 0.070(2) 0.0331(18) 0.0093(17) 0.0008(16) -0.014(2) N12 0.0378(18) 0.066(2) 0.0253(15) 0.0034(15) -0.0004(13) -0.0120(18) N31 0.0412(19) 0.0421(19) 0.0424(18) 0.0035(14) -0.0031(15) -0.0050(17) N32 0.0357(17) 0.0416(18) 0.0414(17) -0.0011(15) 0.0002(13) -0.0016(17) N51 0.0396(19) 0.0392(18) 0.0465(19) 0.0054(15) 0.0009(14) -0.0006(17) N52 0.0374(19) 0.045(2) 0.0455(18) -0.0133(16) -0.0002(15) 0.0030(17) N61 0.0317(16) 0.0332(16) 0.0344(16) -0.0024(13) -0.0011(13) -0.0017(15) N62 0.0296(15) 0.0310(15) 0.0343(15) -0.0056(13) 0.0016(12) -0.0017(14) N81 0.064(2) 0.0391(18) 0.0324(17) 0.0015(14) 0.0058(16) -0.0003(18) N82 0.0376(17) 0.0400(17) 0.0273(15) -0.0009(13) 0.0048(12) -0.0012(16) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N32 1.449(5) . ? C1 N12 1.450(5) . ? C1 C2 1.499(6) . ? C1 H1 0.98 . ? C2 N1 1.313(5) . ? C2 N2 1.354(5) . ? C3 C4 1.351(5) . ? C3 N1 1.372(5) . ? C3 H3 0.93 . ? C4 N2 1.370(5) . ? C4 H4 0.93 . ? C5 N2 1.463(5) . ? C5 H5A 0.96 . ? C5 H5B 0.96 . ? C5 H5C 0.96 . ? C11 N12 1.347(5) . ? C11 C12 1.359(6) . ? C11 H11 0.93 . ? C12 C13 1.386(6) . ? C12 C17 1.501(6) . ? C13 N11 1.336(6) . ? C13 C14 1.509(5) . ? C14 C15 1.545(7) . ? C14 C19 1.555(7) . ? C14 H14 0.98 . ? C15 C16 1.548(9) . ? C15 H15A 0.97 . ? C15 H15B 0.97 . ? C16 C17 1.507(7) . ? C16 H16A 0.97 . ? C16 H16B 0.97 . ? C17 C18 1.476(10) . ? C17 H17 0.98 . ? C18 H18A 0.96 . ? C18 H18B 0.96 . ? C18 H18C 0.96 . ? C19 C20 1.498(7) . ? C19 C21 1.500(6) . ? C19 H19 0.98 . ? C20 H20A 0.96 . ? C20 H20B 0.96 . ? C20 H20C 0.96 . ? C21 H21A 0.96 . ? C21 H21B 0.96 . ? C21 H21C 0.96 . ? C31 N32 1.343(5) . ? C31 C32 1.361(6) . ? C31 H31 0.93 . ? C32 C33 1.391(6) . ? C32 C37 1.510(6) . ? C33 N31 1.333(5) . ? C33 C34 1.512(6) . ? C34 C39 1.531(7) . ? C34 C35 1.544(7) . ? C34 H34 0.98 . ? C35 C36 1.530(8) . ? C35 H35A 0.97 . ? C35 H35B 0.97 . ? C36 C37 1.514(7) . ? C36 H36A 0.97 . ? C36 H36B 0.97 . ? C37 C38 1.511(7) . ? C37 H37 0.98 . ? C38 H38A 0.96 . ? C38 H38B 0.96 . ? C38 H38C 0.96 . ? C39 C40 1.515(7) . ? C39 C41 1.532(7) . ? C39 H39 0.98 . ? C40 H40A 0.96 . ? C40 H40B 0.96 . ? C40 H40C 0.96 . ? C41 H41A 0.96 . ? C41 H41B 0.96 . ? C41 H41C 0.96 . ? C51 N62 1.449(4) . ? C51 N82 1.449(5) . ? C51 C52 1.490(5) . ? C51 H51 0.98 . ? C52 N51 1.315(5) . ? C52 N52 1.356(5) . ? C53 C54 1.350(6) . ? C53 N51 1.376(5) . ? C53 H53 0.93 . ? C54 N52 1.365(6) . ? C54 H54 0.93 . ? C55 N52 1.457(5) . ? C55 H55A 0.96 . ? C55 H55B 0.96 . ? C55 H55C 0.96 . ? C61 N62 1.361(4) . ? C61 C62 1.370(5) . ? C61 H61 0.93 . ? C62 C63 1.406(5) . ? C62 C67 1.503(5) . ? C63 N61 1.333(4) . ? C63 C64 1.499(5) . ? C64 C65 1.530(5) . ? C64 C69 1.544(5) . ? C64 H64 0.98 . ? C65 C66 1.522(6) . ? C65 H65A 0.97 . ? C65 H65B 0.97 . ? C66 C67 1.531(6) . ? C66 H66A 0.97 . ? C66 H66B 0.97 . ? C67 C68 1.499(8) . ? C67 H67 0.98 . ? C68 H68A 0.96 . ? C68 H68B 0.96 . ? C68 H68C 0.96 . ? C69 C71 1.515(7) . ? C69 C70 1.519(6) . ? C69 H69 0.98 . ? C70 H70A 0.96 . ? C70 H70B 0.96 . ? C70 H70C 0.96 . ? C71 H71A 0.96 . ? C71 H71B 0.96 . ? C71 H71C 0.96 . ? C81 N82 1.351(5) . ? C81 C82 1.360(5) . ? C81 H81 0.93 . ? C82 C83 1.396(6) . ? C82 C87 1.515(6) . ? C83 N81 1.333(6) . ? C83 C84 1.502(6) . ? C84 C85 1.481(10) . ? C84 C89 1.50(2) . ? C84 C92 1.55(2) . ? C84 H84 0.98 . ? C85 C86 1.361(11) . ? C85 H85A 0.97 . ? C85 H85B 0.97 . ? C86 C87 1.487(9) . ? C86 H86A 0.97 . ? C86 H86B 0.97 . ? C87 C88 1.510(11) . ? C87 H87 0.98 . ? C88 H88A 0.96 . ? C88 H88B 0.96 . ? C88 H88C 0.96 . ? C89 C90 1.524(17) . ? C89 C91 1.532(15) . ? C89 H89 0.98 . ? C90 H90A 0.96 . ? C90 H90B 0.96 . ? C90 H90C 0.96 . ? C91 H91A 0.96 . ? C91 H91B 0.96 . ? C91 H91C 0.96 . ? C92 C93 1.508(16) . ? C92 C94 1.522(14) . ? C92 H92 0.98 . ? C93 H93A 0.96 . ? C93 H93B 0.96 . ? C93 H93C 0.96 . ? C94 H94A 0.96 . ? C94 H94B 0.96 . ? C94 H94C 0.96 . ? N11 N12 1.359(4) . ? N31 N32 1.358(5) . ? N61 N62 1.355(4) . ? N81 N82 1.359(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N32 C1 N12 112.1(3) . . ? N32 C1 C2 111.7(3) . . ? N12 C1 C2 110.3(3) . . ? N32 C1 H1 107.5 . . ? N12 C1 H1 107.5 . . ? C2 C1 H1 107.5 . . ? N1 C2 N2 111.7(4) . . ? N1 C2 C1 125.9(3) . . ? N2 C2 C1 122.3(3) . . ? C4 C3 N1 111.5(4) . . ? C4 C3 H3 124.2 . . ? N1 C3 H3 124.2 . . ? C3 C4 N2 104.9(4) . . ? C3 C4 H4 127.5 . . ? N2 C4 H4 127.5 . . ? N2 C5 H5A 109.5 . . ? N2 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N2 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N12 C11 C12 107.2(4) . . ? N12 C11 H11 126.4 . . ? C12 C11 H11 126.4 . . ? C11 C12 C13 105.0(4) . . ? C11 C12 C17 131.1(4) . . ? C13 C12 C17 123.9(4) . . ? N11 C13 C12 112.2(3) . . ? N11 C13 C14 123.0(4) . . ? C12 C13 C14 124.7(4) . . ? C13 C14 C15 106.7(4) . . ? C13 C14 C19 113.1(4) . . ? C15 C14 C19 113.7(4) . . ? C13 C14 H14 107.7 . . ? C15 C14 H14 107.7 . . ? C19 C14 H14 107.7 . . ? C14 C15 C16 111.3(5) . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15B 109.4 . . ? C16 C15 H15B 109.4 . . ? H15A C15 H15B 108 . . ? C17 C16 C15 111.9(5) . . ? C17 C16 H16A 109.2 . . ? C15 C16 H16A 109.2 . . ? C17 C16 H16B 109.2 . . ? C15 C16 H16B 109.2 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C12 112.7(5) . . ? C18 C17 C16 115.2(6) . . ? C12 C17 C16 110.0(4) . . ? C18 C17 H17 106.1 . . ? C12 C17 H17 106.1 . . ? C16 C17 H17 106.1 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C21 111.0(5) . . ? C20 C19 C14 111.8(4) . . ? C21 C19 C14 111.5(4) . . ? C20 C19 H19 107.4 . . ? C21 C19 H19 107.4 . . ? C14 C19 H19 107.4 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C19 C21 H21A 109.5 . . ? C19 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C19 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N32 C31 C32 107.4(4) . . ? N32 C31 H31 126.3 . . ? C32 C31 H31 126.3 . . ? C31 C32 C33 104.9(4) . . ? C31 C32 C37 131.2(4) . . ? C33 C32 C37 123.9(4) . . ? N31 C33 C32 111.9(4) . . ? N31 C33 C34 122.4(4) . . ? C32 C33 C34 125.7(4) . . ? C33 C34 C39 111.6(4) . . ? C33 C34 C35 107.9(4) . . ? C39 C34 C35 114.9(4) . . ? C33 C34 H34 107.4 . . ? C39 C34 H34 107.4 . . ? C35 C34 H34 107.4 . . ? C36 C35 C34 113.9(4) . . ? C36 C35 H35A 108.8 . . ? C34 C35 H35A 108.8 . . ? C36 C35 H35B 108.8 . . ? C34 C35 H35B 108.8 . . ? H35A C35 H35B 107.7 . . ? C37 C36 C35 112.4(4) . . ? C37 C36 H36A 109.1 . . ? C35 C36 H36A 109.1 . . ? C37 C36 H36B 109.1 . . ? C35 C36 H36B 109.1 . . ? H36A C36 H36B 107.9 . . ? C32 C37 C38 113.2(4) . . ? C32 C37 C36 107.1(4) . . ? C38 C37 C36 114.4(5) . . ? C32 C37 H37 107.3 . . ? C38 C37 H37 107.3 . . ? C36 C37 H37 107.3 . . ? C37 C38 H38A 109.5 . . ? C37 C38 H38B 109.5 . . ? H38A C38 H38B 109.5 . . ? C37 C38 H38C 109.5 . . ? H38A C38 H38C 109.5 . . ? H38B C38 H38C 109.5 . . ? C40 C39 C34 113.4(4) . . ? C40 C39 C41 110.8(4) . . ? C34 C39 C41 111.3(4) . . ? C40 C39 H39 107 . . ? C34 C39 H39 107 . . ? C41 C39 H39 107 . . ? C39 C40 H40A 109.5 . . ? C39 C40 H40B 109.5 . . ? H40A C40 H40B 109.5 . . ? C39 C40 H40C 109.5 . . ? H40A C40 H40C 109.5 . . ? H40B C40 H40C 109.5 . . ? C39 C41 H41A 109.5 . . ? C39 C41 H41B 109.5 . . ? H41A C41 H41B 109.5 . . ? C39 C41 H41C 109.5 . . ? H41A C41 H41C 109.5 . . ? H41B C41 H41C 109.5 . . ? N62 C51 N82 113.0(3) . . ? N62 C51 C52 110.7(3) . . ? N82 C51 C52 111.1(3) . . ? N62 C51 H51 107.2 . . ? N82 C51 H51 107.2 . . ? C52 C51 H51 107.2 . . ? N51 C52 N52 111.6(3) . . ? N51 C52 C51 125.2(3) . . ? N52 C52 C51 123.1(3) . . ? C54 C53 N51 110.6(4) . . ? C54 C53 H53 124.7 . . ? N51 C53 H53 124.7 . . ? C53 C54 N52 106.0(4) . . ? C53 C54 H54 127 . . ? N52 C54 H54 127 . . ? N52 C55 H55A 109.5 . . ? N52 C55 H55B 109.5 . . ? H55A C55 H55B 109.5 . . ? N52 C55 H55C 109.5 . . ? H55A C55 H55C 109.5 . . ? H55B C55 H55C 109.5 . . ? N62 C61 C62 106.7(3) . . ? N62 C61 H61 126.7 . . ? C62 C61 H61 126.7 . . ? C61 C62 C63 105.0(3) . . ? C61 C62 C67 131.0(4) . . ? C63 C62 C67 124.1(3) . . ? N61 C63 C62 111.7(3) . . ? N61 C63 C64 123.7(3) . . ? C62 C63 C64 124.6(3) . . ? C63 C64 C65 107.8(3) . . ? C63 C64 C69 113.2(3) . . ? C65 C64 C69 114.8(3) . . ? C63 C64 H64 106.8 . . ? C65 C64 H64 106.8 . . ? C69 C64 H64 106.8 . . ? C66 C65 C64 111.6(3) . . ? C66 C65 H65A 109.3 . . ? C64 C65 H65A 109.3 . . ? C66 C65 H65B 109.3 . . ? C64 C65 H65B 109.3 . . ? H65A C65 H65B 108 . . ? C65 C66 C67 112.6(3) . . ? C65 C66 H66A 109.1 . . ? C67 C66 H66A 109.1 . . ? C65 C66 H66B 109.1 . . ? C67 C66 H66B 109.1 . . ? H66A C66 H66B 107.8 . . ? C68 C67 C62 111.6(4) . . ? C68 C67 C66 112.3(4) . . ? C62 C67 C66 108.0(3) . . ? C68 C67 H67 108.3 . . ? C62 C67 H67 108.3 . . ? C66 C67 H67 108.3 . . ? C67 C68 H68A 109.5 . . ? C67 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C67 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? C71 C69 C70 111.7(4) . . ? C71 C69 C64 112.1(3) . . ? C70 C69 C64 111.9(3) . . ? C71 C69 H69 106.9 . . ? C70 C69 H69 106.9 . . ? C64 C69 H69 106.9 . . ? C69 C70 H70A 109.5 . . ? C69 C70 H70B 109.5 . . ? H70A C70 H70B 109.5 . . ? C69 C70 H70C 109.5 . . ? H70A C70 H70C 109.5 . . ? H70B C70 H70C 109.5 . . ? C69 C71 H71A 109.5 . . ? C69 C71 H71B 109.5 . . ? H71A C71 H71B 109.5 . . ? C69 C71 H71C 109.5 . . ? H71A C71 H71C 109.5 . . ? H71B C71 H71C 109.5 . . ? N82 C81 C82 106.5(4) . . ? N82 C81 H81 126.8 . . ? C82 C81 H81 126.8 . . ? C81 C82 C83 105.4(4) . . ? C81 C82 C87 130.1(4) . . ? C83 C82 C87 124.5(4) . . ? N81 C83 C82 111.8(4) . . ? N81 C83 C84 122.8(4) . . ? C82 C83 C84 125.4(4) . . ? C85 C84 C83 107.2(5) . . ? C85 C84 C89 127.3(10) . . ? C83 C84 C89 115.7(8) . . ? C85 C84 C92 103.9(8) . . ? C83 C84 C92 112.9(6) . . ? C89 C84 C92 31.7(8) . . ? C85 C84 H84 100.4 . . ? C83 C84 H84 100.4 . . ? C89 C84 H84 100.4 . . ? C92 C84 H84 129.9 . . ? C86 C85 C84 125.4(7) . . ? C86 C85 H85A 106 . . ? C84 C85 H85A 106 . . ? C86 C85 H85B 106 . . ? C84 C85 H85B 106 . . ? H85A C85 H85B 106.3 . . ? C85 C86 C87 123.8(7) . . ? C85 C86 H86A 106.4 . . ? C87 C86 H86A 106.4 . . ? C85 C86 H86B 106.4 . . ? C87 C86 H86B 106.4 . . ? H86A C86 H86B 106.4 . . ? C86 C87 C88 114.0(7) . . ? C86 C87 C82 107.6(5) . . ? C88 C87 C82 112.1(5) . . ? C86 C87 H87 107.6 . . ? C88 C87 H87 107.6 . . ? C82 C87 H87 107.6 . . ? C87 C88 H88A 109.5 . . ? C87 C88 H88B 109.5 . . ? H88A C88 H88B 109.5 . . ? C87 C88 H88C 109.5 . . ? H88A C88 H88C 109.5 . . ? H88B C88 H88C 109.5 . . ? C84 C89 C90 109(2) . . ? C84 C89 C91 114.1(19) . . ? C90 C89 C91 113(2) . . ? C84 C89 H89 106.6 . . ? C90 C89 H89 106.6 . . ? C91 C89 H89 106.6 . . ? C89 C90 H90A 109.5 . . ? C89 C90 H90B 109.5 . . ? H90A C90 H90B 109.5 . . ? C89 C90 H90C 109.5 . . ? H90A C90 H90C 109.5 . . ? H90B C90 H90C 109.5 . . ? C89 C91 H91A 109.5 . . ? C89 C91 H91B 109.5 . . ? H91A C91 H91B 109.5 . . ? C89 C91 H91C 109.5 . . ? H91A C91 H91C 109.5 . . ? H91B C91 H91C 109.5 . . ? C93 C92 C94 112.2(17) . . ? C93 C92 C84 117.2(13) . . ? C94 C92 C84 107.6(13) . . ? C93 C92 H92 106.4 . . ? C94 C92 H92 106.4 . . ? C84 C92 H92 106.4 . . ? C92 C93 H93A 109.5 . . ? C92 C93 H93B 109.5 . . ? H93A C93 H93B 109.5 . . ? C92 C93 H93C 109.5 . . ? H93A C93 H93C 109.5 . . ? H93B C93 H93C 109.5 . . ? C92 C94 H94A 109.5 . . ? C92 C94 H94B 109.5 . . ? H94A C94 H94B 109.5 . . ? C92 C94 H94C 109.5 . . ? H94A C94 H94C 109.5 . . ? H94B C94 H94C 109.5 . . ? C2 N1 C3 104.4(3) . . ? C2 N2 C4 107.4(3) . . ? C2 N2 C5 128.3(4) . . ? C4 N2 C5 124.3(4) . . ? C13 N11 N12 103.5(3) . . ? C11 N12 N11 112.1(3) . . ? C11 N12 C1 129.6(3) . . ? N11 N12 C1 118.4(3) . . ? C33 N31 N32 104.0(3) . . ? C31 N32 N31 111.9(3) . . ? C31 N32 C1 129.6(4) . . ? N31 N32 C1 118.5(3) . . ? C52 N51 C53 104.8(3) . . ? C52 N52 C54 107.0(3) . . ? C52 N52 C55 126.6(4) . . ? C54 N52 C55 126.4(4) . . ? C63 N61 N62 104.5(3) . . ? N61 N62 C61 112.2(3) . . ? N61 N62 C51 117.1(3) . . ? C61 N62 C51 128.7(3) . . ? C83 N81 N82 103.6(3) . . ? C81 N82 N81 112.6(3) . . ? C81 N82 C51 129.1(3) . . ? N81 N82 C51 118.2(3) . . ?