# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1427 #=============================================================================== data_global #=============================================================================== _audit_creation_date 9-09-99 # 1. SUBMISSION DETAILS _publ_contact_author_name # Name of author for correspondance ; ; _publ_contact_author_address # Address of author for correspondance ; ; _publ_contact_author_phone 'xxxxxxxxxx' _publ_contact_author_fax 'xxxxxxxxxx' _publ_contact_author_email xxx@xx.xx.xx _publ_requested_journal 'Chem. Comm.' _publ_contact_letter ; ; _publ_requested_category FM #=============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=============================================================================== # 3. TITLE AND AUTHOR LIST _publ_section_title ; ? ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Dupont Karl' #<--'Last name, first name' ; Research School of Chemistry National Laboratory Ouchnock Islandia ; # 4. TEXT _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; Burla, M.C., Camalli, M., Cascarano, G.,Giacovazzo, C., Polidori, G., Spagna, R. &Viterbo, D. (1989). SIR. J. Appl. Cryst. 22, 389-393. OpenMoleN, Interactive Intelligent Structure solution (1997) Nonius B.V., Delft, The Netherlands. KappaCCD Operation Manual (1997), Nonius B.V., Delft, The Nederlands. Otwinowski, Z. & Minor, W. (1997), Methods in Enzymology, 276, 307-326. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; #=============================================================================== # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the ? in the data_? line below # by a unique identifier. data_st410 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C68 H68 Cl12 N8 O4' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C68 H68 Cl12 N8 O4' _chemical_formula_weight 1486.79 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 Cl ? 0.132 0.159 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'I 41/a' _symmetry_space_group_name_Hall '-I 4ad' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' 1/2-x,-y,1/2+z 3/4-y,1/4+x,1/4+z 3/4+y,3/4-x,3/4+z -x,-y,-z 1/2+x,+y,1/2-z 3/4+y,1/4-x,1/4-z 3/4-y,3/4+x,3/4-z 1/2+x,1/2+y,1/2+z -x,1/2-y,+z 1/4-y,3/4+x,3/4+z 1/4+y,1/4-x,1/4+z 1/2-x,1/2-y,1/2-z +x,1/2+y,-z 1/4+y,3/4-x,3/4-z 1/4-y,1/4+x,1/4-z _cell_length_a 17.3435(6) _cell_length_b 17.3435(6) _cell_length_c 24.104(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 7250.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 14248 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 32.0 _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.36 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 3072 _exptl_absorpt_coefficient_mu 0.510 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 14248 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 39. mm. Scan angle = 2.0 deg 1 scans of 150 sec per frame. Data collection was divided into 1 sets with the following starting angles and number of frames : Set 1 Theta = 9.59 Omega = 180.00 Kappa = 0.00 64 frames Friedel pairs were not averaged. Internal R = 0.06 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 14248 _diffrn_reflns_av_R_equivalents 0 _diffrn_reflns_av_sigmaI/netI 0.333 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 31.99 _reflns_number_total 5968 _reflns_number_gt 2474 _reflns_threshold_expression >3.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^)+0.0004 Fo^4^)+1.0' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2474 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_all 0.183 _refine_ls_R_factor_gt 0.067 _refine_ls_wR_factor_all 0.140 _refine_ls_wR_factor_ref 0.079 _refine_ls_goodness_of_fit_all 2.483 _refine_ls_goodness_of_fit_ref 1.414 _refine_ls_shift/su_max 0.003 _refine_ls_shift/esd_mean 0.000 _refine_diff_density_max 0.373 _refine_diff_density_min -0.102 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol C1 0.9439(2) 0.0940(2) 0.0947(2) 0.023(2) Uani ? ? C C2 0.8874(2) 0.1384(2) 0.1205(2) 0.023(2) Uani ? ? C C3 0.8451(2) 0.1937(2) 0.0911(2) 0.022(2) Uani ? ? C C4 0.8553(2) 0.1988(2) 0.0342(2) 0.026(2) Uani ? ? C C5 0.9081(2) 0.1519(2) 0.0073(2) 0.026(2) Uani ? ? C C6 0.9531(2) 0.1011(2) 0.0377(2) 0.025(2) Uani ? ? C O 0.8747(1) 0.1289(1) 0.1770(1) 0.026(1) Uani ? ? O C7 0.8165(2) 0.0723(2) 0.1890(2) 0.034(2) Uani ? ? C C8 0.8100(3) 0.0629(3) 0.2507(2) 0.043(2) Uani ? ? C C9 0.7480(3) 0.0053(3) 0.2669(2) 0.050(3) Uani ? ? C N1 0.9146(2) 0.1554(2) -0.0518(1) 0.028(2) Uani ? ? N C10 0.9813(2) 0.1564(2) -0.0720(2) 0.030(2) Uani ? ? C C11 0.9963(3) 0.1503(2) -0.1323(2) 0.030(2) Uani ? ? C C12 1.0705(3) 0.1542(3) -0.1523(2) 0.041(2) Uani ? ? C C13 1.0835(3) 0.1445(3) -0.2079(2) 0.054(3) Uani ? ? C N2 1.0287(3) 0.1311(2) -0.2448(2) 0.052(2) Uani ? ? N C14 0.9560(3) 0.1277(3) -0.2251(2) 0.049(3) Uani ? ? C C15 0.9365(3) 0.1369(3) -0.1704(2) 0.040(2) Uani ? ? C C16 0.9988(2) 0.0444(2) 0.1284(2) 0.025(2) Uani ? ? C C17 0.6814(3) 0.2827(3) -0.1212(2) 0.050(3) Uani ? ? C CL1 0.76019(7) 0.22518(8) -0.10201(6) 0.0558(7) Uani ? ? Cl CL2 0.71095(9) 0.37471(9) -0.14170(8) 0.0722(9) Uani ? ? Cl CL3 0.6257(1) 0.2407(1) -0.17205(8) 0.099(1) Uani ? ? Cl H1 0.8258 0.2348 0.0134 0.0338 Uiso calc C4 H H2 0.9907 0.0706 0.0192 0.0321 Uiso calc C6 H H3 0.8304 0.0245 0.1727 0.0443 Uiso calc C7 H H4 0.7684 0.0889 0.1744 0.0443 Uiso calc C7 H H5 0.7978 0.1114 0.2667 0.0557 Uiso calc C8 H H6 0.8581 0.0454 0.2648 0.0557 Uiso calc C8 H H7 0.7459 0.0011 0.3062 0.0652 Uiso calc C9 H H8 0.6995 0.0224 0.2533 0.0652 Uiso calc C9 H H9 0.7598 -0.0436 0.2513 0.0652 Uiso calc C9 H H10 1.0240 0.1613 -0.0476 0.0405 Uiso calc C10 H H11 1.1123 0.1636 -0.1277 0.0540 Uiso calc C12 H H12 1.1352 0.1475 -0.2207 0.0701 Uiso calc C13 H H13 0.9156 0.1183 -0.2508 0.0672 Uiso calc C14 H H14 0.8843 0.1342 -0.1587 0.0523 Uiso calc C15 H H15 1.0258 0.0106 0.1043 0.0327 Uiso calc C16 H H16 0.9703 0.0150 0.1546 0.0327 Uiso calc C16 H H17 0.6502 0.2875 -0.0890 0.0658 Uiso calc C17 H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol C1 0.022(2) 0.018(2) 0.029(2) -0.004(1) -0.004(2) -0.001(2) C C2 0.024(2) 0.024(2) 0.022(2) -0.007(1) -0.004(2) -0.002(2) C C3 0.017(2) 0.024(2) 0.028(2) -0.005(1) -0.003(2) -0.003(2) C C4 0.025(2) 0.025(2) 0.028(2) -0.001(2) -0.006(2) 0.000(2) C C5 0.027(2) 0.024(2) 0.027(2) -0.002(2) -0.003(2) -0.003(2) C C6 0.024(2) 0.021(2) 0.029(2) -0.000(1) 0.000(2) -0.004(2) C O 0.026(1) 0.027(1) 0.026(1) -0.005(1) -0.001(1) 0.001(1) O C7 0.030(2) 0.033(2) 0.040(2) -0.006(2) -0.000(2) 0.003(2) C C8 0.047(3) 0.043(2) 0.038(2) -0.004(2) 0.011(2) 0.002(2) C C9 0.047(3) 0.050(3) 0.054(3) -0.003(2) 0.019(2) 0.005(2) C N1 0.033(2) 0.027(2) 0.024(2) 0.005(1) -0.002(1) -0.001(1) N C10 0.041(2) 0.024(2) 0.029(2) -0.001(2) -0.005(2) -0.000(2) C C11 0.047(2) 0.018(2) 0.031(2) 0.003(2) 0.006(2) 0.001(2) C C12 0.048(2) 0.034(2) 0.042(2) -0.006(2) 0.008(2) -0.002(2) C C13 0.055(3) 0.048(3) 0.058(3) -0.005(2) 0.019(3) -0.002(3) C N2 0.071(3) 0.056(2) 0.036(2) 0.001(2) 0.015(2) 0.000(2) N C14 0.071(3) 0.054(3) 0.030(2) 0.012(3) -0.004(2) 0.002(2) C C15 0.047(2) 0.040(2) 0.033(2) 0.011(2) 0.001(2) 0.005(2) C C16 0.028(2) 0.019(2) 0.028(2) -0.002(2) 0.001(2) 0.001(2) C C17 0.045(3) 0.065(3) 0.042(3) -0.006(2) -0.009(2) 0.014(2) C CL1 0.0480(7) 0.0651(8) 0.0557(7) 0.0077(6) -0.0027(6) 0.0085(7) Cl CL2 0.0643(8) 0.0557(8) 0.105(1) -0.0059(7) -0.0124(9) 0.0109(8) Cl CL3 0.133(1) 0.078(1) 0.094(1) -0.026(1) -0.0705(8) 0.0139(9) Cl # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.392(5) . . ? C1 C6 1.390(5) . . ? C1 C16 1.519(5) . . ? C2 C3 1.400(5) . . ? C2 O 1.389(5) . . ? C3 C4 1.385(5) . . ? C3 C16 1.519(5) . 7_565 ? C4 C5 1.386(5) . . ? C5 C6 1.386(5) . . ? C5 N1 1.429(5) . . ? O C7 1.438(5) . . ? C7 C8 1.500(6) . . ? C8 C9 1.518(7) . . ? N1 C10 1.256(5) . . ? C10 C11 1.479(6) . . ? C11 C12 1.375(6) . . ? C11 C15 1.404(6) . . ? C12 C13 1.370(7) . . ? C13 N2 1.323(7) . . ? N2 C14 1.349(7) . . ? C14 C15 1.370(7) . . ? C17 CL1 1.753(5) . . ? C17 CL2 1.748(6) . . ? C17 CL3 1.723(5) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 118.2(3) . . . ? C2 C1 C16 121.1(3) . . . ? C6 C1 C16 120.4(3) . . . ? C1 C2 C3 121.4(3) . . . ? C1 C2 O 118.9(3) . . . ? C3 C2 O 119.7(3) . . . ? C2 C3 C4 118.6(3) . . . ? C2 C3 C16 120.5(3) . . 7_565 ? C4 C3 C16 120.8(3) . . 7_565 ? C3 C4 C5 120.6(3) . . . ? C4 C5 C6 119.9(4) . . . ? C4 C5 N1 119.5(3) . . . ? C6 C5 N1 120.6(3) . . . ? C1 C6 C5 121.0(3) . . . ? C2 O C7 113.0(3) . . . ? O C7 C8 109.2(3) . . . ? C7 C8 C9 112.3(4) . . . ? C5 N1 C10 117.5(3) . . . ? N1 C10 C11 122.9(4) . . . ? C10 C11 C12 120.3(4) . . . ? C10 C11 C15 121.7(4) . . . ? C12 C11 C15 118.0(4) . . . ? C11 C12 C13 119.4(4) . . . ? C12 C13 N2 124.2(5) . . . ? C13 N2 C14 116.2(4) . . . ? N2 C14 C15 124.4(5) . . . ? C11 C15 C14 117.8(4) . . . ? CL1 C17 CL2 111.5(3) . . . ? CL1 C17 CL3 112.6(3) . . . ? CL2 C17 CL3 110.4(3) . . . ? data_st430 #=============================================================================== # 5. CHEMICAL DATA _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety 'C77 H77 N9 O8' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C77 H77 N9 O8' _chemical_formula_weight 1256.53 _chemical_melting_point ? _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 International_Tables_Vol_IV_Table_2.3.1 H ? 0.000 0.000 International_Tables_Vol_IV_Table_2.3.1 N ? 0.004 0.003 International_Tables_Vol_IV_Table_2.3.1 O ? 0.008 0.006 International_Tables_Vol_IV_Table_2.3.1 #=============================================================================== # 6. CRYSTAL DATA _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41' _symmetry_space_group_name_Hall ' P 4w' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' -x,-y,1/2+z -y,+x,1/4+z +y,-x,3/4+z _cell_length_a 17.208(1) _cell_length_b 17.208(1) _cell_length_c 23.775(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 7039(1) _cell_formula_units_Z 4 _cell_measurement_temperature 173 _cell_measurement_reflns_used 45424 _cell_measurement_theta_min 1.4 _cell_measurement_theta_max 30.0 _cell_special_details ; Cell parameters refined using Scalepack part of DENZO Z. Otwinowski, W. Minor, 1997 ; _exptl_crystal_description prism _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.19 _exptl_crystal_density_method 'none' _exptl_crystal_F_000 2664 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? #=============================================================================== # 7. EXPERIMENTAL DATA _diffrn_special_details ; ? ; _diffrn_ambient_temperature 173 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type Mo-K\a _diffrn_source xray_tube _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method '\p scans' _diffrn_measurement_details ; 45424 reflections were collected using program Collect ("Collect" Data collection software, Nonius B.V., 1998) The conditions were as follow : crystal to detector distance = 35. mm. Scan angle = 1.6 deg 1 scans of 160 sec per frame. Data collection was divided into 1 set(s) with the following starting angles and number of frames : Set 1 Theta = 10.50 Omega = 180.00 Kappa = 0.00 132 frames Friedel pairs were not averaged. Internal R = 0.06 ; _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 45424 _diffrn_reflns_av_R_equivalents 0.060 _diffrn_reflns_av_sigmaI/netI 0.500 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 2.5 _diffrn_reflns_theta_max 30.05 _reflns_number_total 10545 _reflns_number_gt 2724 _reflns_threshold_expression >2.0\s(I) _computing_structure_solution Direct_methods_(SIR,_Burla_et_al.,_1989) _computing_structure_refinement LSFM_OpenMoleN_(_1997) _computing_molecular_graphics ? _computing_publication_material CIFGEN_IN_OpenMoleN_(_1997) #=============================================================================== # 8. REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme '4Fo^2^/(\s^2^(Fo^2^) + 0.0064 Fo^4^)' _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_expression ? _refine_ls_extinction_coef ? _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 2724 _refine_ls_number_parameters 376 _refine_ls_number_restraints 1 _refine_ls_number_constraints 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_R_factor_all 0.308 _refine_ls_R_factor_gt 0.099 _refine_ls_wR_factor_all 0.224 _refine_ls_wR_factor_ref 0.121 _refine_ls_goodness_of_fit_all 3.220 _refine_ls_goodness_of_fit_ref 1.676 _refine_ls_shift/su_max 0.018 _refine_ls_shift/esd_mean 0.003 _refine_diff_density_max 0.504 _refine_diff_density_min -0.140 #=============================================================================== # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom _atom_site_type_symbol C1 0.4491(8) 0.2823(8) 0.8773 0.052(4) Uiso ? ? C C2 0.4368(8) 0.2752(8) 0.9326(6) 0.054(4) Uiso ? ? C C3 0.3869(8) 0.3223(8) 0.9656(6) 0.055(4) Uiso ? ? C C4 0.3440(8) 0.3780(8) 0.9334(6) 0.058(4) Uiso ? ? C C5 0.3538(8) 0.3881(8) 0.8780(6) 0.051(4) Uiso ? ? C C6 0.4088(8) 0.3426(8) 0.8488(6) 0.057(4) Uiso ? ? C N1 0.3746(7) 0.3149(7) 1.0230(5) 0.059(3) Uiso ? ? N C7 0.369(1) 0.248(1) 1.0437(7) 0.086(5) Uiso ? ? C C8 0.362(1) 0.228(1) 1.1028(7) 0.078(5) Uiso ? ? C C9 0.348(1) 0.151(1) 1.1212(8) 0.104(6) Uiso ? ? C C10 0.345(1) 0.136(1) 1.1769(9) 0.117(7) Uiso ? ? C N2 0.349(1) 0.187(1) 1.2154(7) 0.116(6) Uiso ? ? N C11 0.364(1) 0.263(1) 1.2015(8) 0.094(6) Uiso ? ? C C12 0.369(1) 0.284(1) 1.1432(7) 0.091(6) Uiso ? ? C O1 0.4228(6) 0.3539(6) 0.7934(4) 0.069(3) Uiso ? ? O C13 0.483(1) 0.415(1) 0.7819(8) 0.094(6) Uiso ? ? C C14 0.490(2) 0.422(2) 0.717(1) 0.18(1) Uiso ? ? C C15 0.533(3) 0.500(4) 0.706(2) 0.40(3) Uiso ? ? C C16 0.2984(8) 0.4408(8) 0.8441(6) 0.060(4) Uiso ? ? C C17 0.2429(8) 0.3895(8) 0.8089(5) 0.048(4) Uiso ? ? C C18 0.2591(8) 0.3803(8) 0.7523(6) 0.052(4) Uiso ? ? C C19 0.2162(8) 0.3294(8) 0.7192(6) 0.051(4) Uiso ? ? C C20 0.1557(8) 0.2863(8) 0.7483(6) 0.051(4) Uiso ? ? C C21 0.1401(8) 0.2956(8) 0.8040(6) 0.047(4) Uiso ? ? C C22 0.1831(7) 0.3484(7) 0.8335(5) 0.045(4) Uiso ? ? C N3 0.2302(6) 0.3138(6) 0.6617(5) 0.055(3) Uiso ? ? N C23 0.3026(8) 0.3106(9) 0.6460(6) 0.061(4) Uiso ? ? C C24 0.3266(8) 0.3028(9) 0.5876(6) 0.061(4) Uiso ? ? C C25 0.2742(8) 0.3078(8) 0.5446(6) 0.056(4) Uiso ? ? C C26 0.302(1) 0.2972(9) 0.4872(7) 0.077(5) Uiso ? ? C N4 0.3751(7) 0.2845(8) 0.4760(5) 0.078(4) Uiso ? ? N C27 0.422(1) 0.2776(9) 0.5196(7) 0.074(5) Uiso ? ? C C28 0.4025(9) 0.2881(9) 0.5743(6) 0.069(5) Uiso ? ? C O2 0.1671(5) 0.3627(5) 0.8905(4) 0.057(3) Uiso ? ? O C29 0.108(1) 0.426(1) 0.9006(8) 0.100(6) Uiso ? ? C C30 0.109(1) 0.437(1) 0.9693(8) 0.112(7) Uiso ? ? C C31 0.048(1) 0.493(1) 0.989(1) 0.150(9) Uiso ? ? C C32 0.0834(8) 0.2434(8) 0.8343(6) 0.048(4) Uiso ? ? C C33 0.1268(7) 0.1870(7) 0.8741(5) 0.043(4) Uiso ? ? C C34 0.1279(8) 0.2021(8) 0.9315(5) 0.049(4) Uiso ? ? C C35 0.1739(8) 0.1599(8) 0.9666(6) 0.048(4) Uiso ? ? C C36 0.2223(8) 0.1008(8) 0.9441(6) 0.049(4) Uiso ? ? C C37 0.2205(7) 0.0830(7) 0.8870(5) 0.042(4) Uiso ? ? C C38 0.1695(7) 0.1257(7) 0.8528(5) 0.040(3) Uiso ? ? C N5 0.1771(6) 0.1729(7) 1.0264(5) 0.054(3) Uiso ? ? N C39 0.1819(8) 0.2458(8) 1.0420(6) 0.052(4) Uiso ? ? C C40 0.1775(7) 0.2706(7) 1.1010(5) 0.041(3) Uiso ? ? C C41 0.1676(9) 0.2222(9) 1.1451(6) 0.064(4) Uiso ? ? C C42 0.1676(9) 0.2454(9) 1.1984(6) 0.069(5) Uiso ? ? C N6 0.1752(7) 0.3240(8) 1.2110(5) 0.076(4) Uiso ? ? N C43 0.1800(9) 0.3739(9) 1.1686(6) 0.063(4) Uiso ? ? C C44 0.1835(8) 0.3502(8) 1.1141(6) 0.055(4) Uiso ? ? C O3 0.1630(5) 0.1074(5) 0.7963(4) 0.048(2) Uiso ? ? O C45 0.0988(8) 0.0545(8) 0.7833(6) 0.053(4) Uiso ? ? C C46 0.0869(8) 0.0502(8) 0.7214(6) 0.051(4) Uiso ? ? C C47 0.0226(9) -0.003(1) 0.7029(7) 0.072(5) Uiso ? ? C C48 0.2761(8) 0.0264(8) 0.8621(6) 0.055(4) Uiso ? ? C C49 0.3376(7) 0.0693(7) 0.8261(5) 0.044(4) Uiso ? ? C C50 0.3265(8) 0.0740(8) 0.7686(5) 0.049(4) Uiso ? ? C C51 0.3714(8) 0.1226(8) 0.7357(6) 0.050(4) Uiso ? ? C C52 0.4295(8) 0.1688(8) 0.7610(6) 0.058(4) Uiso ? ? C C53 0.4419(8) 0.1652(8) 0.8180(6) 0.058(4) Uiso ? ? C C54 0.3973(8) 0.1125(8) 0.8497(6) 0.051(4) Uiso ? ? C N7 0.3611(6) 0.1257(6) 0.6746(5) 0.056(3) Uiso ? ? N C55 0.2918(7) 0.1277(7) 0.6582(5) 0.039(3) Uiso ? ? C C56 0.2734(8) 0.1187(8) 0.5970(6) 0.053(4) Uiso ? ? C C57 0.1968(8) 0.1241(8) 0.5803(6) 0.056(4) Uiso ? ? C C58 0.1785(8) 0.1106(8) 0.5235(6) 0.058(4) Uiso ? ? C N8 0.2328(7) 0.0943(7) 0.4852(5) 0.063(3) Uiso ? ? N C59 0.3070(9) 0.0905(9) 0.5007(6) 0.063(4) Uiso ? ? C C60 0.3307(8) 0.1023(8) 0.5552(6) 0.056(4) Uiso ? ? C O4 0.4119(5) 0.1029(5) 0.9082(4) 0.057(3) Uiso ? ? O C61 0.475(1) 0.043(1) 0.9165(8) 0.102(6) Uiso ? ? C C62 0.504(2) 0.046(2) 0.990(1) 0.17(1) Uiso ? ? C C63 0.440(2) 0.013(2) 1.010(1) 0.22(1) Uiso ? ? C C64 0.4970(9) 0.2231(8) 0.8465(6) 0.062(4) Uiso ? ? C C65 0.7335(8) 0.0401(8) 0.7509(6) 0.053(4) Uiso ? ? C C66 0.7039(9) 0.0473(9) 0.8057(6) 0.064(4) Uiso ? ? C C67 0.7381(8) 0.0110(8) 0.8504(6) 0.060(4) Uiso ? ? C C68 0.8006(9) -0.0360(9) 0.8421(7) 0.068(5) Uiso ? ? C C69 0.8316(9) -0.0444(9) 0.7870(6) 0.067(5) Uiso ? ? C C70 0.7976(8) -0.0065(9) 0.7441(6) 0.059(4) Uiso ? ? C O5 0.8394(7) -0.0769(6) 0.8850(5) 0.085(3) Uiso ? ? O C71 0.6968(8) 0.0825(8) 0.7021(6) 0.051(4) Uiso ? ? C C72 0.6169(9) 0.1003(9) 0.6993(6) 0.066(4) Uiso ? ? C C73 0.5828(8) 0.1364(8) 0.6539(6) 0.058(4) Uiso ? ? C C74 0.6283(9) 0.1545(9) 0.6069(7) 0.070(5) Uiso ? ? C C75 0.7060(9) 0.1378(9) 0.6083(6) 0.066(5) Uiso ? ? C C76 0.7403(8) 0.1018(9) 0.6546(6) 0.064(4) Uiso ? ? C O6 0.5955(6) 0.1911(7) 0.5615(5) 0.086(3) Uiso ? ? O N9 0.580(1) -0.187(1) 0.8587(8) 0.135(6) Uiso ? ? N O7 0.5710(9) -0.1290(9) 0.8861(6) 0.143(6) Uiso ? ? O O8 0.539(1) -0.2357(9) 0.8408(7) 0.157(6) Uiso ? ? O C77 0.669(1) -0.208(1) 0.8533(8) 0.101(6) Uiso ? ? C H1 0.4640 0.2349 0.9516 0.0697 Uiso calc C2 H H2 0.3068 0.4094 0.9522 0.0759 Uiso calc C4 H H3 0.4138 0.2208 1.0310 0.1123 Uiso calc C7 H H4 0.3240 0.2258 1.0266 0.1123 Uiso calc C7 H H5 0.3398 0.1102 1.0947 0.1353 Uiso calc C9 H H6 0.3386 0.0835 1.1883 0.1515 Uiso calc C10 H H7 0.3705 0.3013 1.2299 0.1226 Uiso calc C11 H H8 0.3775 0.3362 1.1326 0.1185 Uiso calc C12 H H9 0.5309 0.4001 0.7980 0.1221 Uiso calc C13 H H10 0.4664 0.4631 0.7974 0.1221 Uiso calc C13 H H11 0.4404 0.4221 0.7004 0.2373 Uiso calc C14 H H12 0.5197 0.3793 0.7031 0.2373 Uiso calc C14 H H13 0.5395 0.5067 0.6666 0.5171 Uiso calc C15 H H14 0.5037 0.5417 0.7208 0.5171 Uiso calc C15 H H15 0.5829 0.4989 0.7235 0.5171 Uiso calc C15 H H16 0.3278 0.4732 0.8198 0.0784 Uiso calc C16 H H17 0.2690 0.4721 0.8692 0.0784 Uiso calc C16 H H18 0.3002 0.4093 0.7358 0.0679 Uiso calc C18 H H19 0.1257 0.2499 0.7275 0.0659 Uiso calc C20 H H20 0.3417 0.3134 0.6741 0.0793 Uiso calc C23 H H21 0.2209 0.3180 0.5520 0.0733 Uiso calc C25 H H22 0.2653 0.2996 0.4571 0.1006 Uiso calc C26 H H23 0.4749 0.2642 0.5119 0.0961 Uiso calc C27 H H24 0.4408 0.2852 0.6030 0.0892 Uiso calc C28 H H25 0.0576 0.4099 0.8881 0.1304 Uiso calc C29 H H26 0.1219 0.4725 0.8820 0.1304 Uiso calc C29 H H27 0.1583 0.4566 0.9802 0.1454 Uiso calc C30 H H28 0.1000 0.3884 0.9867 0.1454 Uiso calc C30 H H29 0.0503 0.4983 1.0284 0.1947 Uiso calc C31 H H30 0.0563 0.5424 0.9716 0.1947 Uiso calc C31 H H31 -0.0020 0.4742 0.9782 0.1947 Uiso calc C31 H H32 0.0548 0.2141 0.8074 0.0626 Uiso calc C32 H H33 0.0486 0.2744 0.8558 0.0626 Uiso calc C32 H H34 0.0962 0.2423 0.9464 0.0632 Uiso calc C34 H H35 0.2564 0.0731 0.9683 0.0632 Uiso calc C36 H H36 0.1409 0.2720 1.0231 0.0679 Uiso calc C39 H H37 0.2304 0.2641 1.0284 0.0679 Uiso calc C39 H H38 0.1603 0.1685 1.1376 0.0832 Uiso calc C41 H H39 0.1624 0.2085 1.2278 0.0901 Uiso calc C42 H H40 0.1810 0.4279 1.1765 0.0823 Uiso calc C43 H H41 0.1901 0.3873 1.0849 0.0719 Uiso calc C44 H H42 0.0526 0.0731 0.8006 0.0683 Uiso calc C45 H H43 0.1105 0.0042 0.7973 0.0683 Uiso calc C45 H H44 0.1340 0.0328 0.7048 0.0661 Uiso calc C46 H H45 0.0752 0.1010 0.7082 0.0661 Uiso calc C46 H H46 0.0189 -0.0029 0.6631 0.0933 Uiso calc C47 H H47 0.0337 -0.0548 0.7153 0.0933 Uiso calc C47 H H48 -0.0252 0.0134 0.7188 0.0933 Uiso calc C47 H H49 0.2484 -0.0091 0.8390 0.0712 Uiso calc C48 H H50 0.3015 -0.0012 0.8914 0.0712 Uiso calc C48 H H51 0.2873 0.0433 0.7514 0.0633 Uiso calc C50 H H52 0.4601 0.2027 0.7385 0.0749 Uiso calc C52 H H53 0.5297 0.1965 0.8723 0.0811 Uiso calc C64 H H54 0.5281 0.2482 0.8188 0.0811 Uiso calc C64 H H55 0.6589 0.0782 0.8118 0.0835 Uiso calc C66 H H56 0.7182 0.0186 0.8873 0.0777 Uiso calc C67 H H57 0.8757 -0.0764 0.7806 0.0870 Uiso calc C69 H H58 0.8189 -0.0123 0.7075 0.0766 Uiso calc C70 H H59 0.5849 0.0867 0.7304 0.0860 Uiso calc C72 H H60 0.5290 0.1488 0.6544 0.0757 Uiso calc C73 H H61 0.7375 0.1511 0.5769 0.0858 Uiso calc C75 H H62 0.7942 0.0901 0.6538 0.0833 Uiso calc C76 H # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.34(2) . . ? C1 C6 1.42(2) . . ? C1 C64 1.50(2) . . ? C2 C3 1.42(2) . . ? C3 C4 1.43(2) . . ? C3 N1 1.39(2) . . ? C4 C5 1.34(2) . . ? C5 C6 1.41(2) . . ? C5 C16 1.54(2) . . ? C6 O1 1.35(2) . . ? N1 C7 1.26(2) . . ? C7 C8 1.45(3) . . ? C8 C9 1.42(3) . . ? C8 C12 1.36(2) . . ? C9 C10 1.35(3) . . ? C10 N2 1.28(3) . . ? N2 C11 1.36(3) . . ? C11 C12 1.43(3) . . ? O1 C13 1.49(2) . . ? C13 C14 1.54(3) . . ? C14 C15 1.56(8) . . ? C16 C17 1.55(2) . . ? C17 C18 1.38(2) . . ? C17 C22 1.38(2) . . ? C18 C19 1.39(2) . . ? C19 C20 1.45(2) . . ? C19 N3 1.41(2) . . ? C20 C21 1.36(2) . . ? C21 C22 1.37(2) . . ? C21 C32 1.51(2) . . ? C22 O2 1.40(2) . . ? N3 C23 1.30(2) . . ? C23 C24 1.46(2) . . ? C24 C25 1.37(2) . . ? C24 C28 1.37(2) . . ? C25 C26 1.46(2) . . ? C26 N4 1.31(2) . . ? N4 C27 1.32(2) . . ? C27 C28 1.36(2) . . ? O2 C29 1.51(2) . . ? C29 C30 1.65(3) . . ? C30 C31 1.49(3) . . ? C32 C33 1.55(2) . . ? C33 C34 1.39(2) . . ? C33 C38 1.38(2) . . ? C34 C35 1.36(2) . . ? C35 C36 1.42(2) . . ? C35 N5 1.44(2) . . ? C36 C37 1.39(2) . . ? C37 C38 1.40(2) . . ? C37 C48 1.49(2) . . ? C38 O3 1.38(2) . . ? N5 C39 1.31(2) . . ? C39 C40 1.47(2) . . ? C40 C41 1.35(2) . . ? C40 C44 1.41(2) . . ? C41 C42 1.33(2) . . ? C42 N6 1.39(2) . . ? N6 C43 1.33(2) . . ? C43 C44 1.36(2) . . ? O3 C45 1.46(2) . . ? C45 C46 1.49(2) . . ? C46 C47 1.51(2) . . ? C48 C49 1.55(2) . . ? C49 C50 1.38(2) . . ? C49 C54 1.39(2) . . ? C50 C51 1.38(2) . . ? C51 C52 1.41(2) . . ? C51 N7 1.46(2) . . ? C52 C53 1.37(2) . . ? C53 C54 1.41(2) . . ? C53 C64 1.53(2) . . ? C54 O4 1.42(2) . . ? N7 C55 1.25(2) . . ? C55 C56 1.50(2) . . ? C56 C57 1.38(2) . . ? C56 C60 1.43(2) . . ? C57 C58 1.41(2) . . ? C58 N8 1.33(2) . . ? N8 C59 1.33(2) . . ? C59 C60 1.38(2) . . ? O4 C61 1.51(2) . . ? C61 C62 1.82(4) . . ? C62 C63 1.32(4) . . ? C65 C66 1.40(2) . . ? C65 C70 1.37(2) . . ? C65 C71 1.51(2) . . ? C66 C67 1.37(2) . . ? C67 C68 1.36(2) . . ? C68 C69 1.42(2) . . ? C68 O5 1.41(2) . . ? C69 C70 1.34(2) . . ? C71 C72 1.41(2) . . ? C71 C76 1.39(2) . . ? C72 C73 1.38(2) . . ? C73 C74 1.40(2) . . ? C74 C75 1.37(2) . . ? C74 O6 1.37(2) . . ? C75 C76 1.39(2) . . ? N9 O7 1.20(2) . . ? N9 O8 1.18(2) . . ? N9 C77 1.57(3) . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 117(1) . . . ? C2 C1 C64 120(1) . . . ? C6 C1 C64 122(1) . . . ? C1 C2 C3 125(1) . . . ? C2 C3 C4 113(1) . . . ? C2 C3 N1 125(1) . . . ? C4 C3 N1 120(1) . . . ? C3 C4 C5 123(1) . . . ? C4 C5 C6 119(1) . . . ? C4 C5 C16 120(1) . . . ? C6 C5 C16 118(1) . . . ? C1 C6 C5 119(1) . . . ? C1 C6 O1 118(1) . . . ? C5 C6 O1 121(1) . . . ? C3 N1 C7 118(1) . . . ? N1 C7 C8 127(1) . . . ? C7 C8 C9 122(1) . . . ? C7 C8 C12 120(1) . . . ? C9 C8 C12 117(1) . . . ? C8 C9 C10 119(2) . . . ? C9 C10 N2 124(2) . . . ? C10 N2 C11 119(2) . . . ? N2 C11 C12 118(1) . . . ? C8 C12 C11 120(1) . . . ? C6 O1 C13 113(1) . . . ? O1 C13 C14 107(2) . . . ? C13 C14 C15 106(3) . . . ? C5 C16 C17 109(1) . . . ? C16 C17 C18 117(1) . . . ? C16 C17 C22 121(1) . . . ? C18 C17 C22 120(1) . . . ? C17 C18 C19 121(1) . . . ? C18 C19 C20 115(1) . . . ? C18 C19 N3 125(1) . . . ? C20 C19 N3 119(1) . . . ? C19 C20 C21 123(1) . . . ? C20 C21 C22 118(1) . . . ? C20 C21 C32 121(1) . . . ? C22 C21 C32 120(1) . . . ? C17 C22 C21 121(1) . . . ? C17 C22 O2 117(1) . . . ? C21 C22 O2 120(1) . . . ? C19 N3 C23 116(1) . . . ? N3 C23 C24 123(1) . . . ? C23 C24 C25 121(1) . . . ? C23 C24 C28 120(1) . . . ? C25 C24 C28 118(1) . . . ? C24 C25 C26 118(1) . . . ? C25 C26 N4 121(1) . . . ? C26 N4 C27 116(1) . . . ? N4 C27 C28 125(1) . . . ? C24 C28 C27 119(1) . . . ? C22 O2 C29 114(1) . . . ? O2 C29 C30 103(1) . . . ? C29 C30 C31 111(2) . . . ? C21 C32 C33 110(1) . . . ? C32 C33 C34 119(1) . . . ? C32 C33 C38 120(1) . . . ? C34 C33 C38 119(1) . . . ? C33 C34 C35 120(1) . . . ? C34 C35 C36 119(1) . . . ? C34 C35 N5 123(1) . . . ? C36 C35 N5 117(1) . . . ? C35 C36 C37 120(1) . . . ? C36 C37 C38 117(1) . . . ? C36 C37 C48 121(1) . . . ? C38 C37 C48 120(1) . . . ? C33 C38 C37 121(1) . . . ? C33 C38 O3 119(1) . . . ? C37 C38 O3 119(1) . . . ? C35 N5 C39 115(1) . . . ? N5 C39 C40 123(1) . . . ? C39 C40 C41 124(1) . . . ? C39 C40 C44 119(1) . . . ? C41 C40 C44 115(1) . . . ? C40 C41 C42 123(1) . . . ? C41 C42 N6 119(1) . . . ? C42 N6 C43 118(1) . . . ? N6 C43 C44 122(1) . . . ? C40 C44 C43 119(1) . . . ? C38 O3 C45 113(1) . . . ? O3 C45 C46 110(1) . . . ? C45 C46 C47 114(1) . . . ? C37 C48 C49 110(1) . . . ? C48 C49 C50 118(1) . . . ? C48 C49 C54 122(1) . . . ? C50 C49 C54 118(1) . . . ? C49 C50 C51 121(1) . . . ? C50 C51 C52 119(1) . . . ? C50 C51 N7 121(1) . . . ? C52 C51 N7 119(1) . . . ? C51 C52 C53 120(1) . . . ? C52 C53 C54 118(1) . . . ? C52 C53 C64 120(1) . . . ? C54 C53 C64 121(1) . . . ? C49 C54 C53 122(1) . . . ? C49 C54 O4 117(1) . . . ? C53 C54 O4 120(1) . . . ? C51 N7 C55 115(1) . . . ? N7 C55 C56 119(1) . . . ? C55 C56 C57 118(1) . . . ? C55 C56 C60 123(1) . . . ? C57 C56 C60 118(1) . . . ? C56 C57 C58 118(1) . . . ? C57 C58 N8 122(1) . . . ? C58 N8 C59 119(1) . . . ? N8 C59 C60 122(1) . . . ? C56 C60 C59 118(1) . . . ? C54 O4 C61 109(1) . . . ? O4 C61 C62 107(1) . . . ? C61 C62 C63 95(2) . . . ? C1 C64 C53 108(1) . . . ? C66 C65 C70 116(1) . . . ? C66 C65 C71 121(1) . . . ? C70 C65 C71 121(1) . . . ? C65 C66 C67 121(1) . . . ? C66 C67 C68 120(1) . . . ? C67 C68 C69 119(1) . . . ? C67 C68 O5 124(1) . . . ? C69 C68 O5 116(1) . . . ? C68 C69 C70 119(1) . . . ? C65 C70 C69 122(1) . . . ? C65 C71 C72 123(1) . . . ? C65 C71 C76 120(1) . . . ? C72 C71 C76 115(1) . . . ? C71 C72 C73 123(1) . . . ? C72 C73 C74 119(1) . . . ? C73 C74 C75 118(1) . . . ? C73 C74 O6 119(1) . . . ? C75 C74 O6 121(1) . . . ? C74 C75 C76 121(1) . . . ? C71 C76 C75 121(1) . . . ? O7 N9 O8 135(2) . . . ? O7 N9 C77 111(2) . . . ? O8 N9 C77 112(2) . . . ?