# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Suning Wang' _publ_contact_author_email WANGS@CHEM.QUEENSU.CA _publ_section_title ; Linear and Star-Shaped Benzimidazolyl Derivatives: Syntheses, Photophysical Properties and Use as Highly Efficient Electron Transport Materials in OLEDs ; loop_ _publ_author_name 'Suning Wang.' 'Xiaodong Feng.' 'Sijin Han.' 'Zachary M. Hudson' 'Zheng-Hong Lu.' ; W.White ; # Attachment '1.cif' data_ww145 _database_code_depnum_ccdc_archive 'CCDC 629285' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H18 N4' _chemical_formula_weight 386.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 19.548(6) _cell_length_b 7.058(2) _cell_length_c 13.842(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.886(6) _cell_angle_gamma 90.00 _cell_volume 1909.6(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description 'thing plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.9839 _exptl_absorpt_correction_T_max 0.9959 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4443 _diffrn_reflns_av_R_equivalents 0.0554 _diffrn_reflns_av_sigmaI/netI 0.1803 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.08 _diffrn_reflns_theta_max 28.23 _reflns_number_total 2121 _reflns_number_gt 649 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0299P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2121 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1930 _refine_ls_R_factor_gt 0.0537 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0823 _refine_ls_goodness_of_fit_ref 0.738 _refine_ls_restrained_S_all 0.738 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.31854(15) -0.0400(4) 0.2449(2) 0.0509(9) Uani 1 1 d . . . C2 C -0.38825(16) -0.0745(4) 0.2380(2) 0.0654(10) Uani 1 1 d . . . H2A H -0.4149 -0.0793 0.2930 0.078 Uiso 1 1 calc R . . C3 C -0.41701(15) -0.1012(5) 0.1479(3) 0.0701(10) Uani 1 1 d . . . H3A H -0.4637 -0.1244 0.1419 0.084 Uiso 1 1 calc R . . C4 C -0.37723(16) -0.0943(4) 0.0656(2) 0.0655(10) Uani 1 1 d . . . H4A H -0.3983 -0.1123 0.0056 0.079 Uiso 1 1 calc R . . C5 C -0.30732(14) -0.0614(4) 0.0696(2) 0.0539(9) Uani 1 1 d . . . H5A H -0.2808 -0.0582 0.0145 0.065 Uiso 1 1 calc R . . C6 C -0.27958(13) -0.0337(4) 0.1614(2) 0.0433(8) Uani 1 1 d . . . C7 C -0.21602(14) 0.0042(4) 0.2923(2) 0.0596(9) Uani 1 1 d . . . H7A H -0.1776 0.0231 0.3316 0.072 Uiso 1 1 calc R . . C8 C -0.15185(13) -0.0021(4) 0.1382(2) 0.0438(8) Uani 1 1 d . . . C9 C -0.14833(13) 0.1025(4) 0.0553(2) 0.0559(9) Uani 1 1 d . . . H9A H -0.1859 0.1731 0.0346 0.067 Uiso 1 1 calc R . . C10 C -0.08897(14) 0.1035(4) 0.0020(2) 0.0543(9) Uani 1 1 d . . . H10A H -0.0878 0.1753 -0.0543 0.065 Uiso 1 1 calc R . . C11 C -0.03150(12) 0.0021(4) 0.0294(2) 0.0450(7) Uani 1 1 d . . . C12 C -0.03607(13) -0.0999(5) 0.1151(2) 0.0574(9) Uani 1 1 d . . . H12A H 0.0017 -0.1683 0.1370 0.069 Uiso 1 1 calc R . . C13 C -0.09537(13) -0.1024(5) 0.16871(19) 0.0566(10) Uani 1 1 d . . . H13A H -0.0969 -0.1723 0.2256 0.068 Uiso 1 1 calc R . . N1 N -0.27737(13) -0.0143(4) 0.32673(16) 0.0620(8) Uani 1 1 d . . . N2 N -0.21272(10) -0.0065(3) 0.19382(16) 0.0469(7) 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 0.056(2) 0.048(3) 0.049(2) -0.0057(17) 0.0167(19) -0.0043(16) C2 0.058(2) 0.066(3) 0.073(3) -0.006(2) 0.025(2) -0.0029(18) C3 0.046(2) 0.071(3) 0.093(3) -0.004(2) 0.003(2) -0.0032(17) C4 0.060(2) 0.065(3) 0.071(3) 0.000(2) -0.010(2) 0.0013(18) C5 0.056(2) 0.052(3) 0.054(2) 0.0014(17) 0.0076(18) 0.0011(16) C6 0.0439(18) 0.043(2) 0.043(2) -0.0039(17) 0.0063(15) -0.0018(15) C7 0.066(2) 0.067(3) 0.046(2) -0.002(2) 0.0020(17) -0.0127(19) C8 0.0427(17) 0.051(2) 0.0377(18) 0.0024(18) 0.0069(15) -0.0060(17) C9 0.052(2) 0.062(3) 0.053(2) 0.0117(19) 0.0140(17) 0.0108(16) C10 0.064(2) 0.054(3) 0.045(2) 0.0134(17) 0.0148(17) 0.0072(17) C11 0.0477(19) 0.048(2) 0.0395(19) 0.0020(18) 0.0008(14) -0.0095(18) C12 0.0368(17) 0.083(3) 0.053(2) 0.018(2) -0.0023(16) -0.0015(15) C13 0.0459(19) 0.082(3) 0.042(2) 0.0174(18) 0.0013(16) -0.0032(18) N1 0.0700(17) 0.072(2) 0.0446(17) -0.0063(16) 0.0208(15) -0.0146(15) N2 0.0476(15) 0.056(2) 0.0374(15) -0.0032(14) 0.0116(12) -0.0059(13) _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 C2 1.386(3) . ? C1 N1 1.391(3) . ? C1 C6 1.395(3) . ? C2 C3 1.372(3) . ? C3 C4 1.391(4) . ? C4 C5 1.386(3) . ? C5 C6 1.387(3) . ? C6 N2 1.389(3) . ? C7 N1 1.304(3) . ? C7 N2 1.368(3) . ? C8 C9 1.368(3) . ? C8 C13 1.372(3) . ? C8 N2 1.427(3) . ? C9 C10 1.384(3) . ? C10 C11 1.380(3) . ? C11 C12 1.392(3) . ? C11 C11 1.487(5) 5 ? C12 C13 1.386(3) . ? 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 C2 C1 N1 129.4(3) . . ? C2 C1 C6 119.8(3) . . ? N1 C1 C6 110.8(2) . . ? C3 C2 C1 118.4(3) . . ? C2 C3 C4 120.9(3) . . ? C5 C4 C3 122.4(3) . . ? C4 C5 C6 115.6(3) . . ? C5 C6 N2 131.9(3) . . ? C5 C6 C1 122.9(3) . . ? N2 C6 C1 105.0(2) . . ? N1 C7 N2 114.6(2) . . ? C9 C8 C13 119.1(3) . . ? C9 C8 N2 121.2(3) . . ? C13 C8 N2 119.8(3) . . ? C8 C9 C10 120.2(3) . . ? C11 C10 C9 122.5(3) . . ? C10 C11 C12 116.1(2) . . ? C10 C11 C11 122.5(4) . 5 ? C12 C11 C11 121.4(3) . 5 ? C13 C12 C11 121.9(3) . . ? C8 C13 C12 120.3(3) . . ? C7 N1 C1 103.8(2) . . ? C7 N2 C6 105.7(2) . . ? C7 N2 C8 126.1(2) . . ? C6 N2 C8 128.1(2) . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.129 _refine_diff_density_min -0.148 _refine_diff_density_rms 0.034 # Attachment '2.CIF' data_ww149 _database_code_depnum_ccdc_archive 'CCDC 629286' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H18 N6' _chemical_formula_weight 426.47 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pca2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y, z+1/2' 'x+1/2, -y, z' _cell_length_a 16.7951(9) _cell_length_b 16.5308(12) _cell_length_c 7.4080(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2056.7(2) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 1620 _cell_measurement_theta_min 2.43 _cell_measurement_theta_max 23.75 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 888 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_T_max 0.9957 _exptl_absorpt_process_details 'Bruker SAINT' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Bruker _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7922 _diffrn_reflns_av_R_equivalents 0.0562 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 27.05 _reflns_number_total 3955 _reflns_number_gt 3102 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker Apex2' _computing_cell_refinement 'Bruker Saint' _computing_data_reduction 'Bruker Saint' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker Shelxl' _computing_publication_material 'Bruker Sjelxl' _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^)+(0.0360P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4(3) _refine_ls_number_reflns 3955 _refine_ls_number_parameters 299 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0667 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1029 _refine_ls_wR_factor_gt 0.0922 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.44438(12) 0.35291(11) 0.6491(3) 0.0276(5) Uani 1 1 d . . . N2 N 0.43403(12) 0.47274(11) 0.7917(3) 0.0334(5) Uani 1 1 d . . . N3 N 0.68461(11) 0.22416(10) 0.4422(3) 0.0267(5) Uani 1 1 d . . . N4 N 0.42601(12) 0.12806(11) 0.2262(3) 0.0267(5) Uani 1 1 d . . . N5 N 0.80511(11) 0.17277(11) 0.5071(4) 0.0359(5) Uani 1 1 d . . . N6 N 0.31546(12) 0.06268(12) 0.1336(3) 0.0339(5) Uani 1 1 d . . . C1 C 0.38897(15) 0.41495(13) 0.8822(4) 0.0292(6) Uani 1 1 d . . . C2 C 0.34317(16) 0.42251(15) 1.0384(4) 0.0376(6) Uani 1 1 d . . . H2A H 0.3386 0.4730 1.0988 0.045 Uiso 1 1 calc R . . C3 C 0.30486(16) 0.35493(16) 1.1026(4) 0.0412(7) Uani 1 1 d . . . H3A H 0.2731 0.3590 1.2083 0.049 Uiso 1 1 calc R . . C4 C 0.31172(15) 0.27994(15) 1.0150(4) 0.0365(6) Uani 1 1 d . . . H4A H 0.2845 0.2344 1.0630 0.044 Uiso 1 1 calc R . . C5 C 0.35692(15) 0.27075(14) 0.8613(4) 0.0313(6) Uani 1 1 d . . . H5A H 0.3621 0.2199 0.8027 0.038 Uiso 1 1 calc R . . C6 C 0.39453(14) 0.33983(13) 0.7964(3) 0.0260(5) Uani 1 1 d . . . C7 C 0.46626(15) 0.43361(14) 0.6580(4) 0.0330(6) Uani 1 1 d . . . H7A H 0.5016 0.4581 0.5742 0.040 Uiso 1 1 calc R . . C8 C 0.81192(14) 0.25603(13) 0.4771(4) 0.0290(6) Uani 1 1 d . . . C9 C 0.87882(14) 0.30613(14) 0.4860(4) 0.0349(6) Uani 1 1 d . . . H9A H 0.9299 0.2848 0.5136 0.042 Uiso 1 1 calc R . . C10 C 0.86813(16) 0.38721(14) 0.4535(4) 0.0377(6) Uani 1 1 d . . . H10A H 0.9126 0.4226 0.4615 0.045 Uiso 1 1 calc R . . C11 C 0.79325(16) 0.41917(14) 0.4088(4) 0.0373(7) Uani 1 1 d . . . H11A H 0.7886 0.4754 0.3845 0.045 Uiso 1 1 calc R . . C12 C 0.72632(15) 0.37124(13) 0.3993(4) 0.0331(6) Uani 1 1 d . . . H12A H 0.6755 0.3927 0.3694 0.040 Uiso 1 1 calc R . . C13 C 0.73748(14) 0.28936(12) 0.4362(3) 0.0271(5) Uani 1 1 d . . . C14 C 0.72947(14) 0.15753(13) 0.4850(4) 0.0327(6) Uani 1 1 d . . . H14A H 0.7074 0.1049 0.4975 0.039 Uiso 1 1 calc R . . C15 C 0.37148(14) 0.06428(13) -0.0064(4) 0.0276(6) Uani 1 1 d . . . C16 C 0.36428(15) 0.03503(13) -0.1824(4) 0.0314(6) Uani 1 1 d . . . H16A H 0.3169 0.0092 -0.2222 0.038 Uiso 1 1 calc R . . C17 C 0.42858(16) 0.04505(14) -0.2966(4) 0.0336(6) Uani 1 1 d . . . H17A H 0.4253 0.0261 -0.4175 0.040 Uiso 1 1 calc R . . C18 C 0.49815(16) 0.08260(14) -0.2372(3) 0.0327(6) Uani 1 1 d . . . H18A H 0.5419 0.0870 -0.3179 0.039 Uiso 1 1 calc R . . C19 C 0.50566(14) 0.11342(13) -0.0658(4) 0.0277(5) Uani 1 1 d . . . H19A H 0.5530 0.1398 -0.0275 0.033 Uiso 1 1 calc R . . C20 C 0.44099(13) 0.10415(12) 0.0488(3) 0.0239(5) Uani 1 1 d . . . C21 C 0.35042(15) 0.10095(14) 0.2656(4) 0.0308(6) Uani 1 1 d . . . H21A H 0.3258 0.1094 0.3795 0.037 Uiso 1 1 calc R . . C22 C 0.48082(14) 0.29312(13) 0.5372(4) 0.0275(5) Uani 1 1 d . . . C23 C 0.43528(13) 0.24097(12) 0.4356(4) 0.0265(5) Uani 1 1 d . . . H23A H 0.3789 0.2459 0.4340 0.032 Uiso 1 1 calc R . . C24 C 0.47295(14) 0.18080(13) 0.3350(3) 0.0243(5) Uani 1 1 d . . . C25 C 0.55565(14) 0.17392(13) 0.3353(3) 0.0258(5) Uani 1 1 d . . . H25A H 0.5813 0.1324 0.2683 0.031 Uiso 1 1 calc R . . C26 C 0.59968(14) 0.22875(13) 0.4351(3) 0.0259(5) Uani 1 1 d . . . C27 C 0.56325(14) 0.28823(13) 0.5388(4) 0.0281(5) Uani 1 1 d . . . H27A H 0.5941 0.3247 0.6091 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0275(11) 0.0262(9) 0.0290(11) -0.0021(9) 0.0044(11) 0.0008(8) N2 0.0356(13) 0.0265(9) 0.0380(13) -0.0021(10) 0.0050(12) 0.0025(9) N3 0.0217(10) 0.0284(9) 0.0299(11) -0.0016(10) -0.0024(11) -0.0009(8) N4 0.0224(11) 0.0314(9) 0.0261(11) -0.0010(9) 0.0010(10) -0.0009(9) N5 0.0266(12) 0.0330(10) 0.0481(14) -0.0039(11) -0.0067(12) 0.0005(9) N6 0.0262(12) 0.0389(11) 0.0367(13) -0.0006(11) -0.0013(11) -0.0037(10) C1 0.0301(13) 0.0282(11) 0.0293(13) -0.0012(11) -0.0015(13) 0.0045(10) C2 0.0412(16) 0.0349(12) 0.0366(15) -0.0032(13) 0.0070(16) 0.0081(12) C3 0.0403(17) 0.0482(15) 0.0352(16) 0.0051(14) 0.0105(15) 0.0095(13) C4 0.0333(14) 0.0380(13) 0.0382(15) 0.0095(13) 0.0065(15) 0.0021(11) C5 0.0321(15) 0.0270(11) 0.0348(14) 0.0007(11) -0.0021(14) 0.0044(10) C6 0.0227(13) 0.0296(11) 0.0256(13) 0.0017(11) -0.0011(12) 0.0043(10) C7 0.0352(15) 0.0289(11) 0.0348(15) 0.0035(12) 0.0047(14) 0.0022(11) C8 0.0268(13) 0.0323(11) 0.0280(15) -0.0023(11) -0.0016(12) -0.0010(10) C9 0.0277(13) 0.0431(13) 0.0340(16) -0.0069(13) -0.0029(14) -0.0045(11) C10 0.0388(16) 0.0406(13) 0.0336(15) -0.0048(14) 0.0055(14) -0.0154(12) C11 0.0461(16) 0.0311(11) 0.0347(15) 0.0020(12) 0.0085(14) -0.0060(12) C12 0.0353(15) 0.0331(12) 0.0307(14) 0.0008(12) 0.0021(13) 0.0001(11) C13 0.0283(13) 0.0304(11) 0.0225(12) -0.0044(11) -0.0018(13) -0.0026(10) C14 0.0294(15) 0.0293(11) 0.0396(16) -0.0008(12) -0.0048(14) 0.0016(10) C15 0.0275(13) 0.0232(10) 0.0320(14) 0.0008(11) -0.0047(13) -0.0006(10) C16 0.0324(15) 0.0258(11) 0.0361(15) -0.0020(11) -0.0088(14) 0.0003(11) C17 0.0436(17) 0.0317(12) 0.0254(13) -0.0032(11) -0.0077(14) 0.0090(12) C18 0.0364(15) 0.0337(12) 0.0280(13) 0.0017(12) 0.0029(13) 0.0069(11) C19 0.0234(13) 0.0300(11) 0.0298(13) 0.0017(11) -0.0010(13) 0.0017(10) C20 0.0231(13) 0.0234(10) 0.0252(12) 0.0010(10) -0.0006(12) 0.0040(10) C21 0.0242(14) 0.0356(12) 0.0327(14) 0.0034(12) 0.0047(13) -0.0029(10) C22 0.0285(13) 0.0284(10) 0.0257(12) 0.0018(11) 0.0016(13) 0.0054(10) C23 0.0228(12) 0.0302(11) 0.0265(12) 0.0030(11) -0.0016(13) 0.0001(10) C24 0.0220(13) 0.0280(10) 0.0230(12) 0.0016(10) -0.0024(12) -0.0017(10) C25 0.0252(13) 0.0263(10) 0.0259(13) -0.0022(10) -0.0015(12) 0.0002(10) C26 0.0242(13) 0.0280(10) 0.0256(12) 0.0022(11) -0.0022(13) 0.0007(10) C27 0.0304(13) 0.0281(11) 0.0256(12) -0.0010(11) -0.0022(13) -0.0022(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C7 1.385(3) . ? N1 C6 1.392(3) . ? N1 C22 1.428(3) . ? N2 C7 1.301(3) . ? N2 C1 1.391(3) . ? N3 C14 1.372(3) . ? N3 C13 1.397(3) . ? N3 C26 1.429(3) . ? N4 C21 1.378(3) . ? N4 C20 1.396(3) . ? N4 C24 1.425(3) . ? N5 C14 1.305(3) . ? N5 C8 1.399(3) . ? N6 C21 1.304(3) . ? N6 C15 1.401(3) . ? C1 C2 1.396(4) . ? C1 C6 1.398(3) . ? C2 C3 1.374(4) . ? C2 H2A 0.9500 . ? C3 C4 1.404(4) . ? C3 H3A 0.9500 . ? C4 C5 1.377(4) . ? C4 H4A 0.9500 . ? C5 C6 1.391(3) . ? C5 H5A 0.9500 . ? C7 H7A 0.9500 . ? C8 C9 1.397(3) . ? C8 C13 1.400(3) . ? C9 C10 1.373(3) . ? C9 H9A 0.9500 . ? C10 C11 1.404(4) . ? C10 H10A 0.9500 . ? C11 C12 1.377(3) . ? C11 H11A 0.9500 . ? C12 C13 1.394(3) . ? C12 H12A 0.9500 . ? C14 H14A 0.9500 . ? C15 C16 1.396(4) . ? C15 C20 1.402(3) . ? C16 C17 1.382(4) . ? C16 H16A 0.9500 . ? C17 C18 1.395(4) . ? C17 H17A 0.9500 . ? C18 C19 1.374(4) . ? C18 H18A 0.9500 . ? C19 C20 1.387(3) . ? C19 H19A 0.9500 . ? C21 H21A 0.9500 . ? C22 C23 1.376(3) . ? C22 C27 1.387(3) . ? C23 C24 1.395(3) . ? C23 H23A 0.9500 . ? C24 C25 1.394(3) . ? C25 C26 1.384(3) . ? C25 H25A 0.9500 . ? C26 C27 1.390(3) . ? C27 H27A 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 N1 C6 105.8(2) . . ? C7 N1 C22 125.5(2) . . ? C6 N1 C22 127.25(19) . . ? C7 N2 C1 104.58(19) . . ? C14 N3 C13 106.12(18) . . ? C14 N3 C26 126.82(18) . . ? C13 N3 C26 126.31(17) . . ? C21 N4 C20 105.9(2) . . ? C21 N4 C24 126.1(2) . . ? C20 N4 C24 127.3(2) . . ? C14 N5 C8 104.44(19) . . ? C21 N6 C15 104.10(19) . . ? N2 C1 C2 129.6(2) . . ? N2 C1 C6 110.8(2) . . ? C2 C1 C6 119.6(2) . . ? C3 C2 C1 118.2(2) . . ? C3 C2 H2A 120.9 . . ? C1 C2 H2A 120.9 . . ? C2 C3 C4 121.3(3) . . ? C2 C3 H3A 119.3 . . ? C4 C3 H3A 119.3 . . ? C5 C4 C3 121.7(2) . . ? C5 C4 H4A 119.2 . . ? C3 C4 H4A 119.2 . . ? C4 C5 C6 116.5(2) . . ? C4 C5 H5A 121.8 . . ? C6 C5 H5A 121.8 . . ? C5 C6 N1 132.2(2) . . ? C5 C6 C1 122.8(2) . . ? N1 C6 C1 105.0(2) . . ? N2 C7 N1 113.9(2) . . ? N2 C7 H7A 123.1 . . ? N1 C7 H7A 123.1 . . ? C9 C8 N5 129.9(2) . . ? C9 C8 C13 119.7(2) . . ? N5 C8 C13 110.4(2) . . ? C10 C9 C8 117.7(2) . . ? C10 C9 H9A 121.1 . . ? C8 C9 H9A 121.1 . . ? C9 C10 C11 121.7(2) . . ? C9 C10 H10A 119.1 . . ? C11 C10 H10A 119.1 . . ? C12 C11 C10 121.8(2) . . ? C12 C11 H11A 119.1 . . ? C10 C11 H11A 119.1 . . ? C11 C12 C13 116.0(2) . . ? C11 C12 H12A 122.0 . . ? C13 C12 H12A 122.0 . . ? C12 C13 N3 132.1(2) . . ? C12 C13 C8 123.0(2) . . ? N3 C13 C8 104.90(18) . . ? N5 C14 N3 114.1(2) . . ? N5 C14 H14A 122.9 . . ? N3 C14 H14A 122.9 . . ? C16 C15 N6 128.8(2) . . ? C16 C15 C20 120.5(2) . . ? N6 C15 C20 110.6(2) . . ? C17 C16 C15 117.6(2) . . ? C17 C16 H16A 121.2 . . ? C15 C16 H16A 121.2 . . ? C16 C17 C18 121.0(2) . . ? C16 C17 H17A 119.5 . . ? C18 C17 H17A 119.5 . . ? C19 C18 C17 122.3(3) . . ? C19 C18 H18A 118.9 . . ? C17 C18 H18A 118.9 . . ? C18 C19 C20 116.9(2) . . ? C18 C19 H19A 121.5 . . ? C20 C19 H19A 121.5 . . ? C19 C20 N4 133.3(2) . . ? C19 C20 C15 121.7(2) . . ? N4 C20 C15 104.9(2) . . ? N6 C21 N4 114.5(2) . . ? N6 C21 H21A 122.8 . . ? N4 C21 H21A 122.8 . . ? C23 C22 C27 121.5(2) . . ? C23 C22 N1 120.9(2) . . ? C27 C22 N1 117.6(2) . . ? C22 C23 C24 119.1(2) . . ? C22 C23 H23A 120.4 . . ? C24 C23 H23A 120.4 . . ? C25 C24 C23 120.6(2) . . ? C25 C24 N4 120.2(2) . . ? C23 C24 N4 119.2(2) . . ? C26 C25 C24 118.7(2) . . ? C26 C25 H25A 120.7 . . ? C24 C25 H25A 120.7 . . ? C25 C26 C27 121.6(2) . . ? C25 C26 N3 121.2(2) . . ? C27 C26 N3 117.2(2) . . ? C22 C27 C26 118.4(2) . . ? C22 C27 H27A 120.8 . . ? C26 C27 H27A 120.8 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.05 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.174 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.046 # Attachment '5.cif' data_ww135 _database_code_depnum_ccdc_archive 'CCDC 746268' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C85 H56 Cl2 N12' _chemical_formula_weight 1316.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.2011(16) _cell_length_b 9.2379(11) _cell_length_c 56.398(7) _cell_angle_alpha 90.00 _cell_angle_beta 93.0210(10) _cell_angle_gamma 90.00 _cell_volume 6868.2(14) _cell_formula_units_Z 4 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 9976 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 22.41 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2736 _exptl_absorpt_coefficient_mu 0.152 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9488 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details 'Bruker SAINT' _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 59676 _diffrn_reflns_av_R_equivalents 0.0420 _diffrn_reflns_av_sigmaI/netI 0.0323 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -64 _diffrn_reflns_limit_l_max 64 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 24.21 _reflns_number_total 10992 _reflns_number_gt 8635 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1074P)^2^+16.9098P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 10992 _refine_ls_number_parameters 895 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1140 _refine_ls_R_factor_gt 0.0950 _refine_ls_wR_factor_ref 0.2554 _refine_ls_wR_factor_gt 0.2432 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.7994(2) 0.5479(3) 0.17046(6) 0.1489(10) Uani 1 1 d . . . Cl2 Cl 0.6968(2) 0.4792(4) 0.12486(7) 0.1654(13) Uani 1 1 d . . . C1 C 0.5782(3) 0.9060(5) 0.12371(7) 0.0330(9) Uani 1 1 d . . . C2 C 0.6345(3) 0.9190(4) 0.10325(7) 0.0294(9) Uani 1 1 d . . . C3 C 0.7315(3) 0.9788(4) 0.10514(7) 0.0286(9) Uani 1 1 d . . . C4 C 0.7766(3) 1.0157(5) 0.12778(7) 0.0329(9) Uani 1 1 d . . . C5 C 0.7207(3) 1.0016(5) 0.14802(7) 0.0355(10) Uani 1 1 d . . . C6 C 0.6207(3) 0.9497(5) 0.14577(7) 0.0345(10) Uani 1 1 d . . . C7 C 0.4728(3) 0.8452(4) 0.12189(7) 0.0316(9) Uani 1 1 d . . . C8 C 0.3987(3) 0.9054(5) 0.10630(7) 0.0342(10) Uani 1 1 d . . . H8A H 0.4149 0.9872 0.0970 0.041 Uiso 1 1 calc R . . C9 C 0.3022(3) 0.8477(5) 0.10420(7) 0.0354(10) Uani 1 1 d . . . H9A H 0.2526 0.8884 0.0934 0.043 Uiso 1 1 calc R . . C10 C 0.2783(3) 0.7296(5) 0.11807(8) 0.0363(10) Uani 1 1 d . . . C11 C 0.3509(3) 0.6681(5) 0.13356(8) 0.0407(11) Uani 1 1 d . . . H11A H 0.3344 0.5866 0.1429 0.049 Uiso 1 1 calc R . . C12 C 0.4474(3) 0.7257(5) 0.13538(7) 0.0384(10) Uani 1 1 d . . . H12A H 0.4972 0.6832 0.1460 0.046 Uiso 1 1 calc R . . C13 C 0.1157(4) 0.6559(6) 0.13492(11) 0.0586(14) Uani 1 1 d . . . H13A H 0.1362 0.6773 0.1509 0.070 Uiso 1 1 calc R . . C14 C 0.0270(4) 0.5936(5) 0.10379(11) 0.0561(14) Uani 1 1 d . . . C15 C -0.0491(4) 0.5488(6) 0.08666(16) 0.078(2) Uani 1 1 d . . . H15A H -0.1144 0.5202 0.0912 0.093 Uiso 1 1 calc R . . C16 C -0.0255(6) 0.5481(6) 0.06353(15) 0.083(2) Uani 1 1 d . . . H16A H -0.0767 0.5217 0.0519 0.100 Uiso 1 1 calc R . . C17 C 0.0688(5) 0.5838(6) 0.05615(12) 0.0713(18) Uani 1 1 d . . . H17A H 0.0817 0.5797 0.0397 0.086 Uiso 1 1 calc R . . C18 C 0.1452(4) 0.6257(5) 0.07247(10) 0.0545(13) Uani 1 1 d . . . H18A H 0.2111 0.6491 0.0677 0.065 Uiso 1 1 calc R . . C19 C 0.1216(4) 0.6322(5) 0.09616(9) 0.0463(12) Uani 1 1 d . . . C20 C 0.5936(3) 0.8652(4) 0.07971(7) 0.0293(9) Uani 1 1 d . . . C21 C 0.5786(3) 0.9564(4) 0.06003(7) 0.0312(9) Uani 1 1 d . . . H21A H 0.5947 1.0563 0.0615 0.037 Uiso 1 1 calc R . . C22 C 0.5406(3) 0.9028(5) 0.03846(7) 0.0315(9) Uani 1 1 d . . . H22A H 0.5295 0.9665 0.0254 0.038 Uiso 1 1 calc R . . C23 C 0.5187(3) 0.7564(4) 0.03583(7) 0.0291(9) Uani 1 1 d . . . C24 C 0.5333(3) 0.6643(4) 0.05495(7) 0.0330(9) Uani 1 1 d . . . H24A H 0.5188 0.5640 0.0532 0.040 Uiso 1 1 calc R . . C25 C 0.5691(3) 0.7181(5) 0.07672(7) 0.0346(10) Uani 1 1 d . . . H25A H 0.5772 0.6543 0.0899 0.041 Uiso 1 1 calc R . . C26 C 0.5105(3) 0.7461(5) -0.00825(7) 0.0340(9) Uani 1 1 d . . . H26A H 0.5684 0.8053 -0.0101 0.041 Uiso 1 1 calc R . . C27 C 0.3799(3) 0.6171(4) -0.01589(7) 0.0327(9) Uani 1 1 d . . . C28 C 0.2982(3) 0.5411(5) -0.02652(8) 0.0411(11) Uani 1 1 d . . . H28A H 0.2866 0.5397 -0.0433 0.049 Uiso 1 1 calc R . . C29 C 0.2350(3) 0.4682(5) -0.01199(9) 0.0456(12) Uani 1 1 d . . . H29A H 0.1787 0.4166 -0.0189 0.055 Uiso 1 1 calc R . . C30 C 0.2517(3) 0.4684(5) 0.01237(9) 0.0458(12) Uani 1 1 d . . . H30A H 0.2071 0.4151 0.0218 0.055 Uiso 1 1 calc R . . C31 C 0.3320(3) 0.5443(5) 0.02368(8) 0.0401(10) Uani 1 1 d . . . H31A H 0.3429 0.5453 0.0405 0.048 Uiso 1 1 calc R . . C32 C 0.3948(3) 0.6185(4) 0.00879(7) 0.0301(9) Uani 1 1 d . . . C33 C 0.7916(3) 1.0089(4) 0.08386(7) 0.0309(9) Uani 1 1 d . . . C34 C 0.8374(3) 0.8994(5) 0.07135(7) 0.0327(9) Uani 1 1 d . . . H34A H 0.8236 0.8012 0.0750 0.039 Uiso 1 1 calc R . . C35 C 0.9027(3) 0.9311(4) 0.05373(7) 0.0320(9) Uani 1 1 d . . . H35A H 0.9340 0.8552 0.0454 0.038 Uiso 1 1 calc R . . C36 C 0.9222(3) 1.0745(4) 0.04821(7) 0.0310(9) Uani 1 1 d . . . C37 C 0.8742(3) 1.1851(4) 0.06027(7) 0.0345(10) Uani 1 1 d . . . H37A H 0.8861 1.2834 0.0564 0.041 Uiso 1 1 calc R . . C38 C 0.8100(3) 1.1511(5) 0.07778(7) 0.0355(10) Uani 1 1 d . . . H38A H 0.7775 1.2268 0.0859 0.043 Uiso 1 1 calc R . . C39 C 0.9762(3) 1.2143(4) 0.01322(7) 0.0333(9) Uani 1 1 d . . . H39A H 0.9166 1.2719 0.0116 0.040 Uiso 1 1 calc R . . C40 C 1.1214(3) 1.1233(4) 0.00787(7) 0.0320(9) Uani 1 1 d . . . C41 C 1.2162(3) 1.0857(5) -0.00060(8) 0.0370(10) Uani 1 1 d . . . H41A H 1.2421 1.1334 -0.0139 0.044 Uiso 1 1 calc R . . C42 C 1.2696(3) 0.9779(5) 0.01104(9) 0.0413(11) Uani 1 1 d . . . H42A H 1.3328 0.9481 0.0053 0.050 Uiso 1 1 calc R . . C43 C 1.2336(3) 0.9109(5) 0.03106(9) 0.0433(11) Uani 1 1 d . . . H43A H 1.2742 0.8392 0.0390 0.052 Uiso 1 1 calc R . . C44 C 1.1407(3) 0.9456(5) 0.03968(8) 0.0376(10) Uani 1 1 d . . . H44A H 1.1161 0.8998 0.0533 0.045 Uiso 1 1 calc R . . C45 C 1.0853(3) 1.0517(4) 0.02723(7) 0.0300(9) Uani 1 1 d . . . C46 C 0.8836(3) 1.0695(5) 0.12933(7) 0.0330(9) Uani 1 1 d . . . C47 C 0.9614(3) 0.9825(5) 0.12179(8) 0.0389(10) Uani 1 1 d . . . H47A H 0.9473 0.8863 0.1167 0.047 Uiso 1 1 calc R . . C48 C 1.0591(3) 1.0351(5) 0.12167(8) 0.0425(11) Uani 1 1 d . . . H48A H 1.1120 0.9757 0.1163 0.051 Uiso 1 1 calc R . . C49 C 1.0798(3) 1.1740(5) 0.12932(7) 0.0359(10) Uani 1 1 d . . . C50 C 1.0042(3) 1.2601(5) 0.13738(7) 0.0369(10) Uani 1 1 d . . . H50A H 1.0193 1.3555 0.1428 0.044 Uiso 1 1 calc R . . C51 C 0.9066(3) 1.2082(5) 0.13759(7) 0.0371(10) Uani 1 1 d . . . H51A H 0.8545 1.2674 0.1434 0.045 Uiso 1 1 calc R . . C52 C 1.2431(4) 1.2733(5) 0.14724(9) 0.0485(12) Uani 1 1 d . . . H52A H 1.2217 1.2751 0.1631 0.058 Uiso 1 1 calc R . . C53 C 1.3334(3) 1.2942(5) 0.11728(8) 0.0422(11) Uani 1 1 d . . . C54 C 1.4090(4) 1.3181(6) 0.10143(10) 0.0565(14) Uani 1 1 d . . . H54A H 1.4737 1.3538 0.1068 0.068 Uiso 1 1 calc R . . C55 C 1.3878(5) 1.2887(6) 0.07783(10) 0.0612(15) Uani 1 1 d . . . H55A H 1.4386 1.3048 0.0668 0.073 Uiso 1 1 calc R . . C56 C 1.2938(4) 1.2359(6) 0.06972(9) 0.0528(13) Uani 1 1 d . . . H56A H 1.2821 1.2152 0.0533 0.063 Uiso 1 1 calc R . . C57 C 1.2177(4) 1.2129(5) 0.08484(8) 0.0455(11) Uani 1 1 d . . . H57A H 1.1529 1.1790 0.0792 0.055 Uiso 1 1 calc R . . C58 C 1.2393(3) 1.2414(5) 0.10881(8) 0.0369(10) Uani 1 1 d . . . C59 C 0.7669(3) 1.0367(5) 0.17202(8) 0.0420(11) Uani 1 1 d . . . C60 C 0.8472(4) 0.9538(6) 0.18168(8) 0.0517(13) Uani 1 1 d . . . H60A H 0.8792 0.8848 0.1721 0.062 Uiso 1 1 calc R . . C61 C 0.8804(4) 0.9712(8) 0.20498(9) 0.0689(18) Uani 1 1 d . . . H61A H 0.9336 0.9122 0.2116 0.083 Uiso 1 1 calc R . . C62 C 0.8367(4) 1.0740(9) 0.21860(9) 0.073(2) Uani 1 1 d . . . C63 C 0.7613(4) 1.1651(8) 0.20886(9) 0.0651(16) Uani 1 1 d . . . H63A H 0.7337 1.2393 0.2182 0.078 Uiso 1 1 calc R . . C64 C 0.7271(4) 1.1465(6) 0.18557(8) 0.0482(12) Uani 1 1 d . . . H64A H 0.6763 1.2089 0.1787 0.058 Uiso 1 1 calc R . . C65 C 0.8813(5) 1.2079(13) 0.25536(13) 0.127(4) Uani 1 1 d . . . H65A H 0.8700 1.3004 0.2483 0.152 Uiso 1 1 calc R . . C66 C 0.9143(7) 1.0351(19) 0.28057(14) 0.141(5) Uani 1 1 d . . . C67 C 0.9418(8) 0.962(2) 0.30104(16) 0.167(7) Uani 1 1 d . . . H67A H 0.9618 1.0093 0.3155 0.200 Uiso 1 1 calc R . . C68 C 0.9376(9) 0.804(2) 0.29852(17) 0.162(7) Uani 1 1 d . . . H68A H 0.9573 0.7459 0.3118 0.194 Uiso 1 1 calc R . . C69 C 0.9055(6) 0.7359(14) 0.27713(13) 0.127(4) Uani 1 1 d . . . H69A H 0.9012 0.6333 0.2764 0.153 Uiso 1 1 calc R . . C70 C 0.8797(6) 0.8190(15) 0.25684(12) 0.113(4) Uani 1 1 d . . . H70A H 0.8576 0.7764 0.2421 0.136 Uiso 1 1 calc R . . C71 C 0.8886(5) 0.9665(13) 0.25975(11) 0.093(3) Uani 1 1 d . . . C72 C 0.5633(3) 0.9425(5) 0.16798(7) 0.0362(10) Uani 1 1 d . . . C73 C 0.4898(4) 1.0435(6) 0.17222(8) 0.0474(12) Uani 1 1 d . . . H73A H 0.4670 1.1074 0.1599 0.057 Uiso 1 1 calc R . . C74 C 0.4484(4) 1.0532(6) 0.19438(9) 0.0551(14) Uani 1 1 d . . . H74A H 0.3990 1.1249 0.1972 0.066 Uiso 1 1 calc R . . C75 C 0.4796(4) 0.9578(6) 0.21216(8) 0.0498(13) Uani 1 1 d . . . C76 C 0.5487(4) 0.8512(6) 0.20788(8) 0.0526(13) Uani 1 1 d . . . H76A H 0.5675 0.7823 0.2198 0.063 Uiso 1 1 calc R . . C77 C 0.5910(4) 0.8455(6) 0.18570(8) 0.0467(12) Uani 1 1 d . . . H77A H 0.6399 0.7731 0.1828 0.056 Uiso 1 1 calc R . . C78 C 0.3426(4) 0.9893(9) 0.24063(10) 0.081(2) Uani 1 1 d . . . H78A H 0.2897 1.0043 0.2288 0.097 Uiso 1 1 calc R . . C79 C 0.4224(5) 0.9697(7) 0.27400(9) 0.0690(17) Uani 1 1 d . . . C80 C 0.4524(6) 0.9645(7) 0.29803(10) 0.0742(18) Uani 1 1 d . . . H80A H 0.4039 0.9697 0.3098 0.089 Uiso 1 1 calc R . . C81 C 0.5542(6) 0.9515(8) 0.30421(11) 0.082(2) Uani 1 1 d . . . H81A H 0.5759 0.9457 0.3205 0.098 Uiso 1 1 calc R . . C82 C 0.6256(6) 0.9467(10) 0.28713(11) 0.097(2) Uani 1 1 d . . . H82A H 0.6955 0.9409 0.2920 0.117 Uiso 1 1 calc R . . C83 C 0.5980(5) 0.9500(9) 0.26292(10) 0.083(2) Uani 1 1 d . . . H83A H 0.6470 0.9460 0.2512 0.099 Uiso 1 1 calc R . . C84 C 0.4954(4) 0.9594(7) 0.25694(9) 0.0614(15) Uani 1 1 d . . . C85 C 0.7868(9) 0.5971(9) 0.14261(18) 0.142(4) Uani 1 1 d . . . H85A H 0.8540 0.5939 0.1356 0.170 Uiso 1 1 calc R . . H85B H 0.7622 0.6983 0.1417 0.170 Uiso 1 1 calc R . . N1 N 0.1782(3) 0.6705(4) 0.11657(7) 0.0427(9) Uani 1 1 d . . . N2 N 0.0251(3) 0.6096(5) 0.12838(10) 0.0681(14) Uani 1 1 d . . . N3 N 0.4798(2) 0.7051(4) 0.01338(6) 0.0297(8) Uani 1 1 d . . . N4 N 0.4546(3) 0.6983(4) -0.02636(6) 0.0371(8) Uani 1 1 d . . . N5 N 0.9906(2) 1.1114(4) 0.03049(6) 0.0315(8) Uani 1 1 d . . . N6 N 1.0512(2) 1.2266(4) -0.00086(6) 0.0343(8) Uani 1 1 d . . . N7 N 1.1819(3) 1.2283(4) 0.12863(6) 0.0414(9) Uani 1 1 d . . . N8 N 1.3334(3) 1.3139(5) 0.14180(7) 0.0503(10) Uani 1 1 d . . . N9 N 0.8680(4) 1.0859(9) 0.24317(8) 0.100(2) Uani 1 1 d . . . N10 N 0.9113(5) 1.1923(13) 0.27798(11) 0.127(4) Uani 1 1 d . . . N11 N 0.4404(4) 0.9686(6) 0.23532(7) 0.0635(13) Uani 1 1 d . . . N12 N 0.3269(4) 0.9871(8) 0.26316(9) 0.0913(19) 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 Cl1 0.148(2) 0.121(2) 0.179(3) -0.007(2) 0.024(2) 0.0054(18) Cl2 0.120(2) 0.138(2) 0.231(4) 0.015(2) -0.060(2) 0.0194(18) C1 0.032(2) 0.038(2) 0.029(2) 0.0004(18) 0.0009(17) 0.0022(18) C2 0.029(2) 0.029(2) 0.030(2) -0.0004(17) -0.0010(16) 0.0013(17) C3 0.033(2) 0.028(2) 0.026(2) 0.0000(16) 0.0034(16) 0.0039(17) C4 0.030(2) 0.037(2) 0.031(2) -0.0014(18) 0.0008(17) -0.0009(18) C5 0.036(2) 0.044(3) 0.027(2) -0.0015(19) -0.0010(17) -0.002(2) C6 0.032(2) 0.040(2) 0.031(2) 0.0007(19) 0.0011(18) 0.0025(19) C7 0.036(2) 0.033(2) 0.026(2) -0.0014(17) 0.0028(17) -0.0028(18) C8 0.037(2) 0.035(2) 0.031(2) 0.0024(18) 0.0067(18) -0.0003(19) C9 0.030(2) 0.039(2) 0.038(2) 0.0038(19) 0.0030(18) -0.0018(19) C10 0.032(2) 0.037(2) 0.041(2) -0.004(2) 0.0049(19) 0.0004(19) C11 0.045(3) 0.039(3) 0.039(2) 0.005(2) 0.009(2) -0.007(2) C12 0.038(2) 0.041(3) 0.036(2) 0.002(2) 0.0023(19) 0.002(2) C13 0.055(3) 0.054(3) 0.068(4) 0.007(3) 0.015(3) -0.014(3) C14 0.043(3) 0.039(3) 0.087(4) 0.017(3) 0.000(3) -0.008(2) C15 0.049(3) 0.039(3) 0.142(7) 0.017(4) -0.019(4) -0.018(3) C16 0.100(6) 0.039(3) 0.106(6) 0.018(3) -0.048(5) -0.018(3) C17 0.096(5) 0.036(3) 0.078(4) 0.007(3) -0.033(4) -0.015(3) C18 0.062(3) 0.039(3) 0.061(3) 0.004(2) -0.008(3) -0.003(2) C19 0.042(3) 0.032(2) 0.065(3) 0.011(2) -0.006(2) -0.002(2) C20 0.024(2) 0.035(2) 0.029(2) -0.0021(17) 0.0018(16) 0.0005(17) C21 0.030(2) 0.029(2) 0.035(2) -0.0012(18) 0.0017(17) -0.0029(17) C22 0.028(2) 0.034(2) 0.033(2) 0.0055(18) -0.0001(17) -0.0003(18) C23 0.028(2) 0.031(2) 0.028(2) -0.0011(17) 0.0039(16) 0.0003(17) C24 0.039(2) 0.024(2) 0.035(2) 0.0004(18) 0.0027(18) 0.0002(18) C25 0.039(2) 0.034(2) 0.030(2) 0.0014(18) 0.0028(18) 0.0011(19) C26 0.034(2) 0.035(2) 0.032(2) 0.0016(18) 0.0013(18) 0.0008(19) C27 0.033(2) 0.030(2) 0.035(2) 0.0002(18) -0.0004(18) 0.0034(18) C28 0.039(2) 0.041(3) 0.042(3) -0.005(2) -0.010(2) 0.002(2) C29 0.037(3) 0.039(3) 0.059(3) -0.003(2) -0.012(2) -0.005(2) C30 0.039(3) 0.041(3) 0.058(3) 0.004(2) 0.004(2) -0.010(2) C31 0.044(3) 0.035(2) 0.041(2) 0.000(2) 0.007(2) -0.002(2) C32 0.029(2) 0.027(2) 0.034(2) -0.0035(17) 0.0008(17) -0.0004(17) C33 0.028(2) 0.033(2) 0.031(2) -0.0025(18) -0.0014(17) -0.0007(17) C34 0.035(2) 0.030(2) 0.034(2) 0.0004(18) 0.0043(18) -0.0058(18) C35 0.036(2) 0.029(2) 0.032(2) -0.0060(18) 0.0078(18) -0.0006(18) C36 0.031(2) 0.031(2) 0.031(2) -0.0009(18) 0.0034(17) -0.0018(18) C37 0.040(2) 0.026(2) 0.038(2) 0.0004(18) 0.0081(19) -0.0013(18) C38 0.035(2) 0.034(2) 0.038(2) -0.0043(19) 0.0108(19) 0.0037(19) C39 0.032(2) 0.030(2) 0.038(2) -0.0016(18) 0.0022(18) -0.0023(18) C40 0.031(2) 0.033(2) 0.032(2) -0.0032(18) -0.0012(17) -0.0059(18) C41 0.032(2) 0.039(2) 0.040(2) -0.001(2) 0.0052(19) -0.0094(19) C42 0.028(2) 0.037(2) 0.060(3) -0.003(2) 0.008(2) 0.0016(19) C43 0.039(3) 0.036(2) 0.055(3) 0.001(2) 0.003(2) 0.005(2) C44 0.039(2) 0.035(2) 0.039(2) 0.0028(19) 0.0048(19) -0.0019(19) C45 0.027(2) 0.030(2) 0.033(2) -0.0026(18) 0.0043(17) -0.0073(17) C46 0.032(2) 0.038(2) 0.028(2) -0.0003(18) -0.0015(17) -0.0007(19) C47 0.038(2) 0.031(2) 0.048(3) -0.005(2) 0.003(2) -0.0009(19) C48 0.035(2) 0.043(3) 0.050(3) -0.006(2) 0.008(2) 0.000(2) C49 0.034(2) 0.041(3) 0.033(2) 0.0027(19) 0.0007(18) -0.0057(19) C50 0.043(3) 0.036(2) 0.031(2) -0.0035(19) -0.0047(19) -0.007(2) C51 0.040(2) 0.038(2) 0.034(2) -0.0046(19) -0.0002(18) 0.003(2) C52 0.054(3) 0.050(3) 0.042(3) -0.002(2) 0.003(2) -0.016(2) C53 0.043(3) 0.034(2) 0.049(3) 0.002(2) 0.001(2) -0.012(2) C54 0.048(3) 0.044(3) 0.079(4) 0.004(3) 0.016(3) -0.015(2) C55 0.077(4) 0.045(3) 0.064(4) 0.002(3) 0.033(3) -0.011(3) C56 0.071(4) 0.045(3) 0.043(3) 0.006(2) 0.013(3) -0.007(3) C57 0.055(3) 0.036(3) 0.045(3) 0.004(2) 0.000(2) -0.004(2) C58 0.038(2) 0.031(2) 0.042(3) 0.0001(19) 0.0050(19) -0.0019(19) C59 0.037(2) 0.058(3) 0.031(2) -0.002(2) 0.0024(19) -0.009(2) C60 0.042(3) 0.077(4) 0.037(3) 0.004(2) 0.002(2) 0.003(3) C61 0.043(3) 0.124(6) 0.039(3) 0.006(3) -0.004(2) 0.008(3) C62 0.045(3) 0.143(6) 0.030(3) -0.009(3) -0.002(2) -0.015(4) C63 0.050(3) 0.104(5) 0.042(3) -0.020(3) 0.006(2) -0.008(3) C64 0.043(3) 0.067(3) 0.035(2) -0.008(2) 0.000(2) -0.005(2) C65 0.070(5) 0.249(12) 0.062(4) -0.073(6) 0.013(4) -0.047(6) C66 0.073(5) 0.302(17) 0.045(5) -0.038(8) -0.006(4) -0.010(9) C67 0.090(6) 0.37(2) 0.036(4) 0.011(9) 0.005(4) 0.059(12) C68 0.102(7) 0.34(2) 0.048(5) 0.016(9) 0.002(4) 0.074(12) C69 0.094(6) 0.225(12) 0.064(5) 0.033(6) 0.018(4) 0.043(7) C70 0.081(5) 0.219(12) 0.040(4) 0.002(6) 0.002(3) 0.048(7) C71 0.063(4) 0.180(9) 0.036(4) -0.011(5) 0.005(3) 0.011(5) C72 0.033(2) 0.044(3) 0.032(2) -0.0022(19) 0.0030(18) -0.003(2) C73 0.044(3) 0.061(3) 0.037(3) 0.009(2) 0.003(2) 0.005(2) C74 0.046(3) 0.076(4) 0.044(3) 0.003(3) 0.015(2) 0.013(3) C75 0.047(3) 0.069(3) 0.034(2) 0.005(2) 0.013(2) 0.001(3) C76 0.061(3) 0.065(3) 0.032(2) 0.008(2) 0.004(2) 0.003(3) C77 0.050(3) 0.055(3) 0.035(2) 0.002(2) 0.004(2) 0.006(2) C78 0.050(3) 0.143(7) 0.050(3) 0.009(4) 0.021(3) 0.015(4) C79 0.089(5) 0.079(4) 0.041(3) 0.007(3) 0.019(3) 0.000(4) C80 0.102(5) 0.074(4) 0.048(3) 0.001(3) 0.025(3) 0.001(4) C81 0.105(6) 0.091(5) 0.049(4) -0.003(3) 0.000(4) 0.007(4) C82 0.097(5) 0.142(7) 0.052(4) 0.004(4) -0.005(4) -0.003(5) C83 0.071(4) 0.131(6) 0.047(3) 0.004(4) 0.007(3) 0.000(4) C84 0.067(4) 0.085(4) 0.034(3) 0.005(3) 0.013(3) -0.001(3) C85 0.208(11) 0.077(5) 0.152(9) 0.012(6) 0.113(8) -0.019(6) N1 0.035(2) 0.040(2) 0.053(2) 0.0057(18) 0.0074(18) -0.0090(17) N2 0.051(3) 0.051(3) 0.105(4) 0.007(3) 0.027(3) -0.017(2) N3 0.0322(18) 0.0286(18) 0.0285(18) -0.0006(14) 0.0030(14) -0.0007(15) N4 0.039(2) 0.042(2) 0.0312(19) 0.0050(16) 0.0013(16) 0.0009(17) N5 0.0336(19) 0.0282(18) 0.0333(18) 0.0008(15) 0.0070(15) -0.0025(15) N6 0.0286(18) 0.035(2) 0.040(2) 0.0008(16) 0.0032(15) -0.0017(15) N7 0.041(2) 0.045(2) 0.038(2) -0.0026(17) -0.0014(17) -0.0113(18) N8 0.048(2) 0.049(2) 0.053(3) -0.001(2) -0.0054(19) -0.016(2) N9 0.053(3) 0.214(8) 0.033(3) -0.025(4) -0.002(2) -0.009(4) N10 0.076(4) 0.260(11) 0.045(4) -0.049(6) 0.000(3) -0.035(6) N11 0.064(3) 0.093(4) 0.035(2) 0.008(2) 0.013(2) 0.008(3) N12 0.075(4) 0.141(6) 0.060(3) 0.019(3) 0.028(3) 0.016(4) _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 Cl1 C85 1.635(10) . ? Cl2 C85 1.864(12) . ? C1 C6 1.397(6) . ? C1 C2 1.410(6) . ? C1 C7 1.500(6) . ? C2 C3 1.394(6) . ? C2 C20 1.492(5) . ? C3 C4 1.421(6) . ? C3 C33 1.499(5) . ? C4 C5 1.397(6) . ? C4 C46 1.496(6) . ? C5 C6 1.404(6) . ? C5 C59 1.491(6) . ? C6 C72 1.499(6) . ? C7 C12 1.391(6) . ? C7 C8 1.396(6) . ? C8 C9 1.380(6) . ? C8 H8A 0.9500 . ? C9 C10 1.388(6) . ? C9 H9A 0.9500 . ? C10 C11 1.385(6) . ? C10 N1 1.429(5) . ? C11 C12 1.379(6) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C13 N2 1.306(7) . ? C13 N1 1.363(6) . ? C13 H13A 0.9500 . ? C14 C19 1.390(7) . ? C14 N2 1.396(8) . ? C14 C15 1.418(8) . ? C15 C16 1.357(10) . ? C15 H15A 0.9500 . ? C16 C17 1.374(10) . ? C16 H16A 0.9500 . ? C17 C18 1.384(8) . ? C17 H17A 0.9500 . ? C18 C19 1.389(7) . ? C18 H18A 0.9500 . ? C19 N1 1.384(6) . ? C20 C21 1.399(6) . ? C20 C25 1.405(6) . ? C21 C22 1.383(6) . ? C21 H21A 0.9500 . ? C22 C23 1.390(6) . ? C22 H22A 0.9500 . ? C23 C24 1.379(6) . ? C23 N3 1.422(5) . ? C24 C25 1.384(6) . ? C24 H24A 0.9500 . ? C25 H25A 0.9500 . ? C26 N4 1.306(5) . ? C26 N3 1.359(5) . ? C26 H26A 0.9500 . ? C27 N4 1.394(5) . ? C27 C32 1.395(6) . ? C27 C28 1.396(6) . ? C28 C29 1.375(7) . ? C28 H28A 0.9500 . ? C29 C30 1.380(7) . ? C29 H29A 0.9500 . ? C30 C31 1.396(6) . ? C30 H30A 0.9500 . ? C31 C32 1.392(6) . ? C31 H31A 0.9500 . ? C32 N3 1.391(5) . ? C33 C38 1.383(6) . ? C33 C34 1.389(6) . ? C34 C35 1.380(6) . ? C34 H34A 0.9500 . ? C35 C36 1.389(6) . ? C35 H35A 0.9500 . ? C36 C37 1.397(6) . ? C36 N5 1.423(5) . ? C37 C38 1.371(6) . ? C37 H37A 0.9500 . ? C38 H38A 0.9500 . ? C39 N6 1.307(5) . ? C39 N5 1.367(5) . ? C39 H39A 0.9500 . ? C40 C45 1.383(6) . ? C40 N6 1.401(5) . ? C40 C41 1.407(6) . ? C41 C42 1.368(6) . ? C41 H41A 0.9500 . ? C42 C43 1.393(6) . ? C42 H42A 0.9500 . ? C43 C44 1.380(6) . ? C43 H43A 0.9500 . ? C44 C45 1.391(6) . ? C44 H44A 0.9500 . ? C45 N5 1.387(5) . ? C46 C47 1.388(6) . ? C46 C51 1.391(6) . ? C47 C48 1.378(6) . ? C47 H47A 0.9500 . ? C48 C49 1.376(6) . ? C48 H48A 0.9500 . ? C49 C50 1.373(6) . ? C49 N7 1.441(5) . ? C50 C51 1.376(6) . ? C50 H50A 0.9500 . ? C51 H51A 0.9500 . ? C52 N8 1.301(6) . ? C52 N7 1.355(6) . ? C52 H52A 0.9500 . ? C53 C54 1.392(7) . ? C53 N8 1.395(6) . ? C53 C58 1.396(6) . ? C54 C55 1.372(8) . ? C54 H54A 0.9500 . ? C55 C56 1.388(8) . ? C55 H55A 0.9500 . ? C56 C57 1.368(7) . ? C56 H56A 0.9500 . ? C57 C58 1.391(6) . ? C57 H57A 0.9500 . ? C58 N7 1.389(6) . ? C59 C64 1.390(7) . ? C59 C60 1.395(7) . ? C60 C61 1.373(7) . ? C60 H60A 0.9500 . ? C61 C62 1.368(9) . ? C61 H61A 0.9500 . ? C62 C63 1.394(9) . ? C62 N9 1.429(7) . ? C63 C64 1.377(7) . ? C63 H63A 0.9500 . ? C64 H64A 0.9500 . ? C65 N10 1.323(10) . ? C65 N9 1.327(11) . ? C65 H65A 0.9500 . ? C66 C71 1.362(12) . ? C66 C67 1.369(16) . ? C66 N10 1.460(15) . ? C67 C68 1.47(2) . ? C67 H67A 0.9500 . ? C68 C69 1.407(15) . ? C68 H68A 0.9500 . ? C69 C70 1.405(11) . ? C69 H69A 0.9500 . ? C70 C71 1.376(13) . ? C70 H70A 0.9500 . ? C71 N9 1.462(12) . ? C72 C73 1.376(7) . ? C72 C77 1.377(6) . ? C73 C74 1.393(7) . ? C73 H73A 0.9500 . ? C74 C75 1.381(7) . ? C74 H74A 0.9500 . ? C75 C76 1.372(7) . ? C75 N11 1.434(6) . ? C76 C77 1.398(6) . ? C76 H76A 0.9500 . ? C77 H77A 0.9500 . ? C78 N12 1.299(7) . ? C78 N11 1.353(7) . ? C78 H78A 0.9500 . ? C79 N12 1.382(8) . ? C79 C80 1.393(8) . ? C79 C84 1.400(7) . ? C80 C81 1.376(10) . ? C80 H80A 0.9500 . ? C81 C82 1.383(10) . ? C81 H81A 0.9500 . ? C82 C83 1.395(9) . ? C82 H82A 0.9500 . ? C83 C84 1.381(8) . ? C83 H83A 0.9500 . ? C84 N11 1.389(7) . ? C85 H85A 0.9900 . ? C85 H85B 0.9900 . ? 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 C6 C1 C2 120.0(4) . . ? C6 C1 C7 119.8(4) . . ? C2 C1 C7 120.2(3) . . ? C3 C2 C1 119.5(4) . . ? C3 C2 C20 119.2(3) . . ? C1 C2 C20 121.3(3) . . ? C2 C3 C4 120.2(4) . . ? C2 C3 C33 122.3(3) . . ? C4 C3 C33 117.4(3) . . ? C5 C4 C3 119.8(4) . . ? C5 C4 C46 121.4(4) . . ? C3 C4 C46 118.8(3) . . ? C4 C5 C6 119.5(4) . . ? C4 C5 C59 120.9(4) . . ? C6 C5 C59 119.6(4) . . ? C1 C6 C5 120.7(4) . . ? C1 C6 C72 122.3(4) . . ? C5 C6 C72 117.0(4) . . ? C12 C7 C8 118.7(4) . . ? C12 C7 C1 120.6(4) . . ? C8 C7 C1 120.7(4) . . ? C9 C8 C7 120.8(4) . . ? C9 C8 H8A 119.6 . . ? C7 C8 H8A 119.6 . . ? C8 C9 C10 119.4(4) . . ? C8 C9 H9A 120.3 . . ? C10 C9 H9A 120.3 . . ? C11 C10 C9 120.5(4) . . ? C11 C10 N1 119.2(4) . . ? C9 C10 N1 120.3(4) . . ? C12 C11 C10 119.7(4) . . ? C12 C11 H11A 120.2 . . ? C10 C11 H11A 120.2 . . ? C11 C12 C7 120.9(4) . . ? C11 C12 H12A 119.6 . . ? C7 C12 H12A 119.6 . . ? N2 C13 N1 113.5(5) . . ? N2 C13 H13A 123.2 . . ? N1 C13 H13A 123.2 . . ? C19 C14 N2 110.1(5) . . ? C19 C14 C15 118.7(6) . . ? N2 C14 C15 131.2(6) . . ? C16 C15 C14 117.8(6) . . ? C16 C15 H15A 121.1 . . ? C14 C15 H15A 121.1 . . ? C15 C16 C17 123.2(6) . . ? C15 C16 H16A 118.4 . . ? C17 C16 H16A 118.4 . . ? C16 C17 C18 120.4(7) . . ? C16 C17 H17A 119.8 . . ? C18 C17 H17A 119.8 . . ? C17 C18 C19 117.4(6) . . ? C17 C18 H18A 121.3 . . ? C19 C18 H18A 121.3 . . ? N1 C19 C18 132.3(4) . . ? N1 C19 C14 105.2(5) . . ? C18 C19 C14 122.5(5) . . ? C21 C20 C25 117.7(4) . . ? C21 C20 C2 122.3(4) . . ? C25 C20 C2 120.0(4) . . ? C22 C21 C20 120.8(4) . . ? C22 C21 H21A 119.6 . . ? C20 C21 H21A 119.6 . . ? C21 C22 C23 120.4(4) . . ? C21 C22 H22A 119.8 . . ? C23 C22 H22A 119.8 . . ? C24 C23 C22 119.8(4) . . ? C24 C23 N3 121.3(4) . . ? C22 C23 N3 118.8(4) . . ? C23 C24 C25 119.9(4) . . ? C23 C24 H24A 120.0 . . ? C25 C24 H24A 120.0 . . ? C24 C25 C20 121.3(4) . . ? C24 C25 H25A 119.3 . . ? C20 C25 H25A 119.3 . . ? N4 C26 N3 115.2(4) . . ? N4 C26 H26A 122.4 . . ? N3 C26 H26A 122.4 . . ? N4 C27 C32 110.6(4) . . ? N4 C27 C28 129.5(4) . . ? C32 C27 C28 119.9(4) . . ? C29 C28 C27 118.0(4) . . ? C29 C28 H28A 121.0 . . ? C27 C28 H28A 121.0 . . ? C28 C29 C30 121.5(4) . . ? C28 C29 H29A 119.3 . . ? C30 C29 H29A 119.3 . . ? C29 C30 C31 122.2(4) . . ? C29 C30 H30A 118.9 . . ? C31 C30 H30A 118.9 . . ? C32 C31 C30 115.7(4) . . ? C32 C31 H31A 122.2 . . ? C30 C31 H31A 122.2 . . ? N3 C32 C31 132.2(4) . . ? N3 C32 C27 105.1(3) . . ? C31 C32 C27 122.7(4) . . ? C38 C33 C34 118.6(4) . . ? C38 C33 C3 118.8(4) . . ? C34 C33 C3 122.3(4) . . ? C35 C34 C33 121.1(4) . . ? C35 C34 H34A 119.5 . . ? C33 C34 H34A 119.5 . . ? C34 C35 C36 119.6(4) . . ? C34 C35 H35A 120.2 . . ? C36 C35 H35A 120.2 . . ? C35 C36 C37 119.6(4) . . ? C35 C36 N5 121.2(4) . . ? C37 C36 N5 119.2(4) . . ? C38 C37 C36 119.8(4) . . ? C38 C37 H37A 120.1 . . ? C36 C37 H37A 120.1 . . ? C37 C38 C33 121.3(4) . . ? C37 C38 H38A 119.3 . . ? C33 C38 H38A 119.3 . . ? N6 C39 N5 114.3(4) . . ? N6 C39 H39A 122.8 . . ? N5 C39 H39A 122.8 . . ? C45 C40 N6 110.8(4) . . ? C45 C40 C41 120.0(4) . . ? N6 C40 C41 129.2(4) . . ? C42 C41 C40 117.6(4) . . ? C42 C41 H41A 121.2 . . ? C40 C41 H41A 121.2 . . ? C41 C42 C43 121.5(4) . . ? C41 C42 H42A 119.2 . . ? C43 C42 H42A 119.2 . . ? C44 C43 C42 122.0(4) . . ? C44 C43 H43A 119.0 . . ? C42 C43 H43A 119.0 . . ? C43 C44 C45 116.1(4) . . ? C43 C44 H44A 122.0 . . ? C45 C44 H44A 122.0 . . ? C40 C45 N5 105.3(4) . . ? C40 C45 C44 122.8(4) . . ? N5 C45 C44 131.8(4) . . ? C47 C46 C51 119.0(4) . . ? C47 C46 C4 120.1(4) . . ? C51 C46 C4 120.9(4) . . ? C48 C47 C46 120.3(4) . . ? C48 C47 H47A 119.8 . . ? C46 C47 H47A 119.8 . . ? C49 C48 C47 119.8(4) . . ? C49 C48 H48A 120.1 . . ? C47 C48 H48A 120.1 . . ? C50 C49 C48 120.6(4) . . ? C50 C49 N7 120.3(4) . . ? C48 C49 N7 119.1(4) . . ? C49 C50 C51 119.9(4) . . ? C49 C50 H50A 120.1 . . ? C51 C50 H50A 120.1 . . ? C50 C51 C46 120.4(4) . . ? C50 C51 H51A 119.8 . . ? C46 C51 H51A 119.8 . . ? N8 C52 N7 115.0(4) . . ? N8 C52 H52A 122.5 . . ? N7 C52 H52A 122.5 . . ? C54 C53 N8 130.8(4) . . ? C54 C53 C58 119.4(5) . . ? N8 C53 C58 109.8(4) . . ? C55 C54 C53 118.3(5) . . ? C55 C54 H54A 120.8 . . ? C53 C54 H54A 120.8 . . ? C54 C55 C56 121.5(5) . . ? C54 C55 H55A 119.3 . . ? C56 C55 H55A 119.3 . . ? C57 C56 C55 121.5(5) . . ? C57 C56 H56A 119.3 . . ? C55 C56 H56A 119.3 . . ? C56 C57 C58 117.2(5) . . ? C56 C57 H57A 121.4 . . ? C58 C57 H57A 121.4 . . ? N7 C58 C57 132.3(4) . . ? N7 C58 C53 105.6(4) . . ? C57 C58 C53 122.1(4) . . ? C64 C59 C60 119.2(4) . . ? C64 C59 C5 120.6(4) . . ? C60 C59 C5 120.1(4) . . ? C61 C60 C59 120.4(5) . . ? C61 C60 H60A 119.8 . . ? C59 C60 H60A 119.8 . . ? C62 C61 C60 119.8(5) . . ? C62 C61 H61A 120.1 . . ? C60 C61 H61A 120.1 . . ? C61 C62 C63 120.7(5) . . ? C61 C62 N9 119.2(6) . . ? C63 C62 N9 120.0(6) . . ? C64 C63 C62 119.5(5) . . ? C64 C63 H63A 120.3 . . ? C62 C63 H63A 120.3 . . ? C63 C64 C59 120.1(5) . . ? C63 C64 H64A 120.0 . . ? C59 C64 H64A 120.0 . . ? N10 C65 N9 115.6(11) . . ? N10 C65 H65A 122.2 . . ? N9 C65 H65A 122.2 . . ? C71 C66 C67 122.7(16) . . ? C71 C66 N10 111.9(10) . . ? C67 C66 N10 125.4(12) . . ? C66 C67 C68 113.7(13) . . ? C66 C67 H67A 123.2 . . ? C68 C67 H67A 123.2 . . ? C69 C68 C67 122.5(12) . . ? C69 C68 H68A 118.7 . . ? C67 C68 H68A 118.7 . . ? C70 C69 C68 120.1(13) . . ? C70 C69 H69A 119.9 . . ? C68 C69 H69A 119.9 . . ? C71 C70 C69 115.4(9) . . ? C71 C70 H70A 122.3 . . ? C69 C70 H70A 122.3 . . ? C66 C71 C70 125.4(11) . . ? C66 C71 N9 103.3(11) . . ? C70 C71 N9 131.2(7) . . ? C73 C72 C77 118.5(4) . . ? C73 C72 C6 120.5(4) . . ? C77 C72 C6 120.6(4) . . ? C72 C73 C74 120.9(5) . . ? C72 C73 H73A 119.6 . . ? C74 C73 H73A 119.6 . . ? C75 C74 C73 119.6(5) . . ? C75 C74 H74A 120.2 . . ? C73 C74 H74A 120.2 . . ? C76 C75 C74 120.4(4) . . ? C76 C75 N11 119.1(5) . . ? C74 C75 N11 120.5(5) . . ? C75 C76 C77 119.0(5) . . ? C75 C76 H76A 120.5 . . ? C77 C76 H76A 120.5 . . ? C72 C77 C76 121.5(5) . . ? C72 C77 H77A 119.3 . . ? C76 C77 H77A 119.3 . . ? N12 C78 N11 114.7(6) . . ? N12 C78 H78A 122.7 . . ? N11 C78 H78A 122.7 . . ? N12 C79 C80 129.8(6) . . ? N12 C79 C84 110.4(5) . . ? C80 C79 C84 119.7(6) . . ? C81 C80 C79 118.3(6) . . ? C81 C80 H80A 120.9 . . ? C79 C80 H80A 120.9 . . ? C80 C81 C82 121.2(6) . . ? C80 C81 H81A 119.4 . . ? C82 C81 H81A 119.4 . . ? C81 C82 C83 121.9(7) . . ? C81 C82 H82A 119.1 . . ? C83 C82 H82A 119.1 . . ? C84 C83 C82 116.3(6) . . ? C84 C83 H83A 121.9 . . ? C82 C83 H83A 121.9 . . ? C83 C84 N11 132.8(5) . . ? C83 C84 C79 122.5(5) . . ? N11 C84 C79 104.6(5) . . ? Cl1 C85 Cl2 112.5(5) . . ? Cl1 C85 H85A 109.1 . . ? Cl2 C85 H85A 109.1 . . ? Cl1 C85 H85B 109.1 . . ? Cl2 C85 H85B 109.1 . . ? H85A C85 H85B 107.8 . . ? C13 N1 C19 106.6(4) . . ? C13 N1 C10 126.0(4) . . ? C19 N1 C10 127.1(4) . . ? C13 N2 C14 104.6(4) . . ? C26 N3 C32 105.6(3) . . ? C26 N3 C23 126.6(3) . . ? C32 N3 C23 127.4(3) . . ? C26 N4 C27 103.5(3) . . ? C39 N5 C45 106.0(3) . . ? C39 N5 C36 126.6(3) . . ? C45 N5 C36 127.4(3) . . ? C39 N6 C40 103.6(3) . . ? C52 N7 C58 105.6(4) . . ? C52 N7 C49 127.3(4) . . ? C58 N7 C49 127.1(4) . . ? C52 N8 C53 104.1(4) . . ? C65 N9 C62 126.2(8) . . ? C65 N9 C71 107.1(7) . . ? C62 N9 C71 126.6(7) . . ? C65 N10 C66 102.1(8) . . ? C78 N11 C84 106.0(4) . . ? C78 N11 C75 127.3(5) . . ? C84 N11 C75 126.7(5) . . ? C78 N12 C79 104.2(5) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.21 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.671 _refine_diff_density_min -1.088 _refine_diff_density_rms 0.073 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons 1 0.212 -0.122 0.181 73.2 16.8 2 0.788 0.121 0.819 73.2 16.9 3 0.788 0.378 0.319 73.2 16.9 4 0.212 0.621 0.681 73.2 16.7 _platon_squeeze_details ;Disordered water molecules were removed by Squeeze. ;