# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Lijuan Jiao' _publ_contact_author_email 'jiao421@mail.ahnu.edu.cn ' loop_ _publ_author_name 'Min Zhang' 'Erhong Hao' 'Jinyuan Zhou' 'Changjiang Yu' 'Guifeng Bai' 'Fengyun Wang' 'Lijuan Jiao' data_110804a_0m _database_code_depnum_ccdc_archive 'CCDC 863478' #TrackingRef 'BODIPY-1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H16 B F2 N3' _chemical_formula_weight 347.17 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.162(3) _cell_length_b 8.550(3) _cell_length_c 12.743(5) _cell_angle_alpha 82.561(4) _cell_angle_beta 81.071(4) _cell_angle_gamma 72.465(4) _cell_volume 834.4(6) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3232 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 27.34 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.382 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9731 _exptl_absorpt_correction_T_max 0.9769 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 7025 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 27.62 _reflns_number_total 3720 _reflns_number_gt 2760 _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^)+(0.1100P)^2^+3.5975P] 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 SHELXL _refine_ls_extinction_coef 0.028(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3720 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1195 _refine_ls_R_factor_gt 0.1015 _refine_ls_wR_factor_ref 0.3389 _refine_ls_wR_factor_gt 0.3297 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 B1 B 0.3624(8) 0.2014(7) 0.8507(5) 0.0444(13) Uani 1 1 d . . . C1 C 0.6864(7) 0.0516(7) 0.8211(5) 0.0511(13) Uani 1 1 d . . . H1 H 0.6802 -0.0443 0.8632 0.061 Uiso 1 1 calc R . . C2 C 0.8367(8) 0.0807(8) 0.7693(5) 0.0600(16) Uani 1 1 d . . . H2 H 0.9480 0.0093 0.7700 0.072 Uiso 1 1 calc R . . C3 C 0.7915(7) 0.2356(7) 0.7164(5) 0.0522(14) Uani 1 1 d . . . H3 H 0.8671 0.2881 0.6751 0.063 Uiso 1 1 calc R . . C4 C 0.6118(7) 0.2997(6) 0.7358(4) 0.0422(11) Uani 1 1 d . . . C5 C 0.4956(7) 0.4550(6) 0.7080(4) 0.0419(11) Uani 1 1 d . . . C6 C 0.5686(6) 0.5809(6) 0.6427(4) 0.0414(11) Uani 1 1 d . . . C7 C 0.6747(8) 0.5481(7) 0.5472(4) 0.0508(13) Uani 1 1 d . . . H7 H 0.6967 0.4463 0.5209 0.061 Uiso 1 1 calc R . . C8 C 0.7488(8) 0.6651(8) 0.4900(5) 0.0555(15) Uani 1 1 d . . . H8 H 0.8206 0.6403 0.4265 0.067 Uiso 1 1 calc R . . C9 C 0.7166(8) 0.8179(7) 0.5267(5) 0.0514(13) Uani 1 1 d . . . C10 C 0.6084(8) 0.8521(7) 0.6201(5) 0.0545(14) Uani 1 1 d . . . H10 H 0.5842 0.9552 0.6449 0.065 Uiso 1 1 calc R . . C11 C 0.5347(7) 0.7371(7) 0.6779(4) 0.0479(12) Uani 1 1 d . . . H11 H 0.4620 0.7636 0.7408 0.057 Uiso 1 1 calc R . . C12 C 0.7984(9) 0.9449(9) 0.4647(6) 0.0696(19) Uani 1 1 d . . . H12A H 0.9203 0.9109 0.4701 0.104 Uiso 1 1 calc R . . H12B H 0.7462 1.0494 0.4936 0.104 Uiso 1 1 calc R . . H12C H 0.7804 0.9550 0.3912 0.104 Uiso 1 1 calc R . . C13 C 0.3225(6) 0.4896(6) 0.7444(4) 0.0399(11) Uani 1 1 d . . . C14 C 0.1822(7) 0.6292(7) 0.7206(5) 0.0497(13) Uani 1 1 d . . . H14 H 0.1907 0.7220 0.6757 0.060 Uiso 1 1 calc R . . C15 C 0.0345(7) 0.6043(7) 0.7741(5) 0.0531(14) Uani 1 1 d . . . H15 H -0.0763 0.6760 0.7720 0.064 Uiso 1 1 calc R . . C16 C 0.0795(6) 0.4477(6) 0.8347(4) 0.0414(11) Uani 1 1 d . . . C17 C -0.0426(6) 0.3822(6) 0.9057(4) 0.0439(12) Uani 1 1 d . . . C18 C -0.2209(7) 0.4480(8) 0.9218(5) 0.0558(15) Uani 1 1 d . . . H18 H -0.2841 0.5463 0.8887 0.067 Uiso 1 1 calc R . . C19 C -0.2887(8) 0.3438(8) 0.9948(5) 0.0606(16) Uani 1 1 d . . . H19 H -0.4054 0.3580 1.0189 0.073 Uiso 1 1 calc R . . C20 C -0.1551(8) 0.2170(8) 1.0252(5) 0.0585(15) Uani 1 1 d . . . H20 H -0.1639 0.1294 1.0751 0.070 Uiso 1 1 calc R . . F1 F 0.3523(4) 0.1799(5) 0.9611(3) 0.0661(11) Uani 1 1 d . . . F2 F 0.2978(4) 0.0866(4) 0.8165(3) 0.0671(11) Uani 1 1 d . . . N1 N 0.5490(5) 0.1828(5) 0.8019(3) 0.0422(10) Uani 1 1 d . . . N2 N 0.2539(5) 0.3777(5) 0.8147(3) 0.0384(9) Uani 1 1 d . . . N3 N -0.0060(6) 0.2387(6) 0.9707(4) 0.0521(12) Uani 1 1 d . . . H3A H 0.0958 0.1726 0.9762 0.062 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 B1 0.043(3) 0.041(3) 0.046(3) -0.001(2) 0.004(2) -0.012(2) C1 0.048(3) 0.043(3) 0.054(3) 0.000(2) -0.006(2) -0.004(2) C2 0.044(3) 0.058(4) 0.065(4) -0.004(3) 0.000(3) 0.001(3) C3 0.039(3) 0.060(3) 0.055(3) -0.004(3) 0.003(2) -0.014(2) C4 0.039(3) 0.044(3) 0.042(3) 0.000(2) -0.002(2) -0.012(2) C5 0.045(3) 0.044(3) 0.037(2) -0.004(2) -0.004(2) -0.014(2) C6 0.042(3) 0.043(3) 0.040(3) -0.004(2) -0.002(2) -0.013(2) C7 0.058(3) 0.052(3) 0.047(3) -0.012(2) 0.004(2) -0.023(3) C8 0.052(3) 0.069(4) 0.050(3) -0.008(3) 0.007(2) -0.029(3) C9 0.053(3) 0.052(3) 0.054(3) 0.002(2) -0.003(2) -0.027(3) C10 0.055(3) 0.044(3) 0.067(4) -0.008(3) -0.004(3) -0.018(3) C11 0.052(3) 0.045(3) 0.046(3) -0.007(2) 0.002(2) -0.016(2) C12 0.064(4) 0.067(4) 0.084(5) 0.006(3) 0.001(3) -0.039(3) C13 0.041(3) 0.038(2) 0.040(2) -0.0013(19) -0.0021(19) -0.012(2) C14 0.046(3) 0.045(3) 0.055(3) 0.002(2) -0.008(2) -0.009(2) C15 0.043(3) 0.044(3) 0.065(4) -0.001(2) -0.003(2) -0.004(2) C16 0.036(2) 0.042(3) 0.045(3) -0.008(2) -0.004(2) -0.009(2) C17 0.037(3) 0.046(3) 0.047(3) -0.008(2) -0.003(2) -0.010(2) C18 0.034(3) 0.054(3) 0.073(4) -0.004(3) -0.002(3) -0.006(2) C19 0.038(3) 0.075(4) 0.069(4) -0.016(3) 0.009(3) -0.021(3) C20 0.048(3) 0.069(4) 0.059(4) -0.001(3) 0.005(3) -0.026(3) F1 0.0503(19) 0.079(2) 0.0488(19) 0.0175(17) 0.0007(15) -0.0010(17) F2 0.052(2) 0.0452(19) 0.104(3) -0.0172(18) 0.0086(19) -0.0177(15) N1 0.038(2) 0.041(2) 0.043(2) -0.0003(17) -0.0012(17) -0.0075(18) N2 0.038(2) 0.037(2) 0.039(2) -0.0051(16) -0.0004(16) -0.0098(17) N3 0.041(2) 0.056(3) 0.055(3) 0.000(2) -0.001(2) -0.014(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F1 1.387(7) . ? B1 F2 1.388(7) . ? B1 N1 1.522(7) . ? B1 N2 1.552(7) . ? C1 N1 1.354(7) . ? C1 C2 1.376(8) . ? C1 H1 0.9300 . ? C2 C3 1.377(8) . ? C2 H2 0.9300 . ? C3 C4 1.397(7) . ? C3 H3 0.9300 . ? C4 N1 1.389(6) . ? C4 C5 1.418(7) . ? C5 C13 1.371(7) . ? C5 C6 1.485(7) . ? C6 C7 1.387(7) . ? C6 C11 1.399(7) . ? C7 C8 1.392(8) . ? C7 H7 0.9300 . ? C8 C9 1.381(8) . ? C8 H8 0.9300 . ? C9 C10 1.375(8) . ? C9 C12 1.516(8) . ? C10 C11 1.379(8) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 N2 1.406(6) . ? C13 C14 1.420(7) . ? C14 C15 1.351(8) . ? C14 H14 0.9300 . ? C15 C16 1.431(8) . ? C15 H15 0.9300 . ? C16 N2 1.365(6) . ? C16 C17 1.431(7) . ? C17 N3 1.369(7) . ? C17 C18 1.386(7) . ? C18 C19 1.375(9) . ? C18 H18 0.9300 . ? C19 C20 1.351(9) . ? C19 H19 0.9300 . ? C20 N3 1.355(7) . ? C20 H20 0.9300 . ? N3 H3A 0.8600 . ? 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 F1 B1 F2 108.6(5) . . ? F1 B1 N1 110.1(5) . . ? F2 B1 N1 111.2(4) . . ? F1 B1 N2 110.1(4) . . ? F2 B1 N2 109.5(5) . . ? N1 B1 N2 107.3(4) . . ? N1 C1 C2 110.1(5) . . ? N1 C1 H1 124.9 . . ? C2 C1 H1 124.9 . . ? C1 C2 C3 107.2(5) . . ? C1 C2 H2 126.4 . . ? C3 C2 H2 126.4 . . ? C2 C3 C4 107.8(5) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? N1 C4 C3 107.6(5) . . ? N1 C4 C5 119.3(4) . . ? C3 C4 C5 133.0(5) . . ? C13 C5 C4 120.7(5) . . ? C13 C5 C6 121.3(5) . . ? C4 C5 C6 117.9(5) . . ? C7 C6 C11 117.7(5) . . ? C7 C6 C5 122.1(5) . . ? C11 C6 C5 120.2(5) . . ? C6 C7 C8 121.1(5) . . ? C6 C7 H7 119.5 . . ? C8 C7 H7 119.5 . . ? C9 C8 C7 120.5(5) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 118.5(5) . . ? C10 C9 C12 121.0(6) . . ? C8 C9 C12 120.5(6) . . ? C9 C10 C11 121.6(5) . . ? C9 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C10 C11 C6 120.5(5) . . ? C10 C11 H11 119.7 . . ? C6 C11 H11 119.7 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C5 C13 N2 122.0(4) . . ? C5 C13 C14 130.5(5) . . ? N2 C13 C14 107.5(4) . . ? C15 C14 C13 108.5(5) . . ? C15 C14 H14 125.8 . . ? C13 C14 H14 125.8 . . ? C14 C15 C16 107.7(5) . . ? C14 C15 H15 126.2 . . ? C16 C15 H15 126.2 . . ? N2 C16 C15 108.7(4) . . ? N2 C16 C17 127.4(5) . . ? C15 C16 C17 123.9(5) . . ? N3 C17 C18 105.8(5) . . ? N3 C17 C16 126.6(5) . . ? C18 C17 C16 127.6(5) . . ? C19 C18 C17 108.6(5) . . ? C19 C18 H18 125.7 . . ? C17 C18 H18 125.7 . . ? C20 C19 C18 107.5(5) . . ? C20 C19 H19 126.2 . . ? C18 C19 H19 126.2 . . ? C19 C20 N3 108.5(5) . . ? C19 C20 H20 125.7 . . ? N3 C20 H20 125.7 . . ? C1 N1 C4 107.4(4) . . ? C1 N1 B1 125.6(4) . . ? C4 N1 B1 126.9(4) . . ? C16 N2 C13 107.6(4) . . ? C16 N2 B1 128.6(4) . . ? C13 N2 B1 123.6(4) . . ? C20 N3 C17 109.5(5) . . ? C20 N3 H3A 125.3 . . ? C17 N3 H3A 125.3 . . ? _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 27.62 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.415 _refine_diff_density_min -0.319 _refine_diff_density_rms 0.083 #===END # Attachment 'BODIPY-1e.cif' data_110728b_0m _database_code_depnum_ccdc_archive 'CCDC 863479' #TrackingRef 'BODIPY-1e.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 B F2 N3' _chemical_formula_weight 375.22 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' B B 0.0013 0.0007 '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' F F 0.0171 0.0103 '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 10.0277(7) _cell_length_b 17.2775(12) _cell_length_c 11.1652(8) _cell_angle_alpha 90.00 _cell_angle_beta 94.1610(10) _cell_angle_gamma 90.00 _cell_volume 1929.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6227 _cell_measurement_theta_min 2.18 _cell_measurement_theta_max 26.62 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9726 _exptl_absorpt_correction_T_max 0.9779 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 16484 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0211 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.04 _diffrn_reflns_theta_max 27.63 _reflns_number_total 4466 _reflns_number_gt 3089 _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^)+(0.1200P)^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 4466 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0684 _refine_ls_R_factor_gt 0.0463 _refine_ls_wR_factor_ref 0.1858 _refine_ls_wR_factor_gt 0.1624 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.003 _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 B1 B 0.32433(18) 0.25561(11) 0.96702(18) 0.0560(5) Uani 1 1 d . . . C1 C 0.23551(19) 0.13489(10) 0.85252(16) 0.0629(4) Uani 1 1 d . . . H1 H 0.3076 0.1030 0.8754 0.075 Uiso 1 1 calc R . . C2 C 0.1234(2) 0.11242(11) 0.78102(16) 0.0678(5) Uani 1 1 d . . . H2 H 0.1068 0.0636 0.7482 0.081 Uiso 1 1 calc R . . C3 C 0.04117(19) 0.17611(11) 0.76783(14) 0.0622(5) Uani 1 1 d . . . H3 H -0.0413 0.1782 0.7241 0.075 Uiso 1 1 calc R . . C4 C 0.10409(16) 0.23715(10) 0.83204(14) 0.0532(4) Uani 1 1 d . . . C5 C 0.06629(15) 0.31431(9) 0.84796(13) 0.0498(4) Uani 1 1 d . . . C6 C 0.14708(15) 0.36380(9) 0.91883(13) 0.0492(4) Uani 1 1 d . . . C7 C 0.13214(16) 0.44296(10) 0.94275(14) 0.0563(4) Uani 1 1 d . . . H7 H 0.0618 0.4743 0.9135 0.068 Uiso 1 1 calc R . . C8 C 0.23903(18) 0.46553(10) 1.01642(15) 0.0602(4) Uani 1 1 d . . . H8 H 0.2552 0.5152 1.0462 0.072 Uiso 1 1 calc R . . C9 C 0.32125(16) 0.39988(9) 1.03964(13) 0.0520(4) Uani 1 1 d . . . C10 C 0.44205(16) 0.40018(10) 1.11702(14) 0.0564(4) Uani 1 1 d . . . C11 C 0.5148(2) 0.46372(12) 1.15837(17) 0.0749(5) Uani 1 1 d . . . H11 H 0.4951 0.5151 1.1398 0.090 Uiso 1 1 calc R . . C12 C 0.6228(2) 0.43750(15) 1.23274(17) 0.0832(6) Uani 1 1 d . . . H12 H 0.6886 0.4680 1.2722 0.100 Uiso 1 1 calc R . . C13 C 0.6146(2) 0.35938(14) 1.23709(18) 0.0774(6) Uani 1 1 d . . . H13 H 0.6732 0.3267 1.2812 0.093 Uiso 1 1 calc R . . C14 C -0.06089(15) 0.34320(9) 0.78539(13) 0.0494(4) Uani 1 1 d . . . C15 C -0.05760(17) 0.38076(10) 0.67476(14) 0.0568(4) Uani 1 1 d . . . C16 C -0.17730(19) 0.40370(10) 0.61546(14) 0.0611(5) Uani 1 1 d . . . H16 H -0.1752 0.4288 0.5419 0.073 Uiso 1 1 calc R . . C17 C -0.29938(17) 0.39072(9) 0.66134(15) 0.0581(4) Uani 1 1 d . . . C18 C -0.30005(16) 0.35457(9) 0.77221(15) 0.0592(4) Uani 1 1 d . . . H18 H -0.3814 0.3460 0.8050 0.071 Uiso 1 1 calc R . . C19 C -0.18293(16) 0.33073(9) 0.83593(14) 0.0533(4) Uani 1 1 d . . . C20 C 0.0724(2) 0.39704(16) 0.61879(19) 0.0928(7) Uani 1 1 d . . . H20A H 0.1164 0.4402 0.6588 0.139 Uiso 1 1 calc R . . H20B H 0.0542 0.4090 0.5352 0.139 Uiso 1 1 calc R . . H20C H 0.1290 0.3523 0.6269 0.139 Uiso 1 1 calc R . . C21 C -0.4261(2) 0.41529(13) 0.5921(2) 0.0836(6) Uani 1 1 d . . . H21A H -0.4159 0.4670 0.5626 0.125 Uiso 1 1 calc R . . H21B H -0.4985 0.4139 0.6438 0.125 Uiso 1 1 calc R . . H21C H -0.4449 0.3807 0.5258 0.125 Uiso 1 1 calc R . . C22 C -0.1894(2) 0.29361(14) 0.95754(16) 0.0778(6) Uani 1 1 d . . . H22A H -0.1485 0.2434 0.9570 0.117 Uiso 1 1 calc R . . H22B H -0.2811 0.2885 0.9756 0.117 Uiso 1 1 calc R . . H22C H -0.1426 0.3253 1.0174 0.117 Uiso 1 1 calc R . . F1 F 0.33876(11) 0.22028(6) 1.07930(9) 0.0755(3) Uani 1 1 d . . . F2 F 0.44731(10) 0.25947(7) 0.92024(12) 0.0838(4) Uani 1 1 d . . . N1 N 0.22463(13) 0.20976(8) 0.88402(11) 0.0541(4) Uani 1 1 d . . . N2 N 0.26611(12) 0.33855(8) 0.97977(11) 0.0491(3) Uani 1 1 d . . . N3 N 0.50680(15) 0.33716(10) 1.16644(14) 0.0689(4) Uani 1 1 d . . . H3A H 0.4823 0.2899 1.1542 0.083 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 B1 0.0428(9) 0.0582(11) 0.0670(11) -0.0002(8) 0.0035(8) 0.0054(8) C1 0.0689(11) 0.0555(10) 0.0652(10) -0.0051(8) 0.0111(8) 0.0127(8) C2 0.0830(13) 0.0595(10) 0.0606(10) -0.0124(8) 0.0042(9) 0.0036(9) C3 0.0639(11) 0.0686(11) 0.0533(9) -0.0088(7) -0.0010(7) -0.0003(8) C4 0.0491(8) 0.0596(10) 0.0510(8) -0.0013(7) 0.0032(6) 0.0034(7) C5 0.0453(8) 0.0576(10) 0.0465(7) 0.0018(6) 0.0036(6) 0.0036(6) C6 0.0439(8) 0.0557(9) 0.0481(8) 0.0017(6) 0.0027(6) 0.0061(6) C7 0.0566(9) 0.0565(10) 0.0554(8) 0.0031(7) 0.0018(7) 0.0074(7) C8 0.0660(10) 0.0528(10) 0.0613(9) -0.0020(7) 0.0012(8) 0.0000(8) C9 0.0508(8) 0.0575(9) 0.0479(8) 0.0025(7) 0.0055(6) -0.0029(7) C10 0.0509(9) 0.0675(11) 0.0506(8) 0.0045(7) 0.0028(7) -0.0054(7) C11 0.0787(12) 0.0765(13) 0.0670(11) 0.0076(9) -0.0112(9) -0.0193(10) C12 0.0716(12) 0.1063(17) 0.0688(12) 0.0070(11) -0.0144(9) -0.0271(12) C13 0.0614(11) 0.0937(16) 0.0743(12) 0.0102(10) -0.0141(9) -0.0062(10) C14 0.0490(8) 0.0534(9) 0.0452(7) -0.0020(6) -0.0015(6) 0.0039(6) C15 0.0592(10) 0.0619(10) 0.0495(8) 0.0016(7) 0.0040(7) 0.0036(8) C16 0.0727(12) 0.0583(10) 0.0502(8) 0.0058(7) -0.0094(8) 0.0012(8) C17 0.0604(10) 0.0488(9) 0.0619(9) -0.0018(7) -0.0165(8) 0.0002(7) C18 0.0464(9) 0.0622(10) 0.0677(10) 0.0035(8) -0.0056(7) -0.0028(7) C19 0.0485(8) 0.0579(9) 0.0525(8) 0.0050(7) -0.0030(7) -0.0028(7) C20 0.0745(14) 0.137(2) 0.0694(12) 0.0241(13) 0.0222(10) 0.0075(13) C21 0.0713(12) 0.0835(14) 0.0906(14) 0.0069(11) -0.0308(10) 0.0050(10) C22 0.0609(11) 0.1050(16) 0.0673(11) 0.0266(10) 0.0039(9) -0.0009(10) F1 0.0782(7) 0.0648(7) 0.0799(7) 0.0129(5) -0.0194(5) 0.0001(5) F2 0.0462(6) 0.0878(8) 0.1195(9) -0.0197(7) 0.0203(6) 0.0037(5) N1 0.0498(7) 0.0554(8) 0.0576(7) -0.0036(6) 0.0064(6) 0.0081(6) N2 0.0412(6) 0.0550(8) 0.0509(7) 0.0010(5) 0.0021(5) 0.0021(5) N3 0.0597(9) 0.0716(10) 0.0732(9) 0.0056(7) -0.0107(7) -0.0032(7) _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 B1 F2 1.375(2) . ? B1 F1 1.392(2) . ? B1 N1 1.533(2) . ? B1 N2 1.558(2) . ? C1 N1 1.347(2) . ? C1 C2 1.387(3) . ? C1 H1 0.9300 . ? C2 C3 1.376(3) . ? C2 H2 0.9300 . ? C3 C4 1.399(2) . ? C3 H3 0.9300 . ? C4 N1 1.386(2) . ? C4 C5 1.401(2) . ? C5 C6 1.386(2) . ? C5 C14 1.495(2) . ? C6 N2 1.4000(18) . ? C6 C7 1.404(2) . ? C7 C8 1.360(2) . ? C7 H7 0.9300 . ? C8 C9 1.415(2) . ? C8 H8 0.9300 . ? C9 N2 1.350(2) . ? C9 C10 1.436(2) . ? C10 N3 1.364(2) . ? C10 C11 1.379(3) . ? C11 C12 1.392(3) . ? C11 H11 0.9300 . ? C12 C13 1.353(3) . ? C12 H12 0.9300 . ? C13 N3 1.347(2) . ? C13 H13 0.9300 . ? C14 C15 1.398(2) . ? C14 C19 1.401(2) . ? C15 C16 1.386(2) . ? C15 C20 1.512(3) . ? C16 C17 1.379(3) . ? C16 H16 0.9300 . ? C17 C18 1.387(2) . ? C17 C21 1.500(2) . ? C18 C19 1.391(2) . ? C18 H18 0.9300 . ? C19 C22 1.507(2) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? N3 H3A 0.8600 . ? 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 F2 B1 F1 109.01(14) . . ? F2 B1 N1 111.03(15) . . ? F1 B1 N1 109.77(14) . . ? F2 B1 N2 110.03(14) . . ? F1 B1 N2 109.64(14) . . ? N1 B1 N2 107.35(13) . . ? N1 C1 C2 109.96(16) . . ? N1 C1 H1 125.0 . . ? C2 C1 H1 125.0 . . ? C3 C2 C1 106.99(16) . . ? C3 C2 H2 126.5 . . ? C1 C2 H2 126.5 . . ? C2 C3 C4 107.67(16) . . ? C2 C3 H3 126.2 . . ? C4 C3 H3 126.2 . . ? N1 C4 C3 107.72(15) . . ? N1 C4 C5 120.52(14) . . ? C3 C4 C5 131.76(15) . . ? C6 C5 C4 120.48(14) . . ? C6 C5 C14 120.29(14) . . ? C4 C5 C14 119.21(14) . . ? C5 C6 N2 121.85(14) . . ? C5 C6 C7 130.08(14) . . ? N2 C6 C7 108.07(13) . . ? C8 C7 C6 107.71(14) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? C7 C8 C9 107.70(15) . . ? C7 C8 H8 126.1 . . ? C9 C8 H8 126.1 . . ? N2 C9 C8 109.04(14) . . ? N2 C9 C10 126.74(14) . . ? C8 C9 C10 124.21(15) . . ? N3 C10 C11 105.99(15) . . ? N3 C10 C9 126.64(15) . . ? C11 C10 C9 127.36(17) . . ? C10 C11 C12 108.08(19) . . ? C10 C11 H11 126.0 . . ? C12 C11 H11 126.0 . . ? C13 C12 C11 107.40(17) . . ? C13 C12 H12 126.3 . . ? C11 C12 H12 126.3 . . ? N3 C13 C12 108.16(17) . . ? N3 C13 H13 125.9 . . ? C12 C13 H13 125.9 . . ? C15 C14 C19 120.31(14) . . ? C15 C14 C5 119.60(14) . . ? C19 C14 C5 120.06(13) . . ? C16 C15 C14 118.67(15) . . ? C16 C15 C20 119.47(16) . . ? C14 C15 C20 121.86(15) . . ? C17 C16 C15 122.50(15) . . ? C17 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? C16 C17 C18 117.82(14) . . ? C16 C17 C21 120.28(17) . . ? C18 C17 C21 121.90(18) . . ? C17 C18 C19 122.10(16) . . ? C17 C18 H18 119.0 . . ? C19 C18 H18 119.0 . . ? C18 C19 C14 118.57(14) . . ? C18 C19 C22 119.80(15) . . ? C14 C19 C22 121.62(14) . . ? C15 C20 H20A 109.5 . . ? C15 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C15 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C17 C21 H21A 109.5 . . ? C17 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C17 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C19 C22 H22A 109.5 . . ? C19 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C19 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C1 N1 C4 107.66(14) . . ? C1 N1 B1 126.32(14) . . ? C4 N1 B1 125.97(14) . . ? C9 N2 C6 107.47(13) . . ? C9 N2 B1 128.66(13) . . ? C6 N2 B1 123.65(13) . . ? C13 N3 C10 110.35(17) . . ? C13 N3 H3A 124.8 . . ? C10 N3 H3A 124.8 . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.225 _refine_diff_density_min -0.170 _refine_diff_density_rms 0.034 #===END # Attachment 'BODIPY-6.cif' data_110905a_0m _database_code_depnum_ccdc_archive 'CCDC 863480' #TrackingRef 'BODIPY-6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C46 H40 B2 F4 N6 O2' _chemical_formula_weight 806.46 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P21/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 36.086(17) _cell_length_b 13.768(7) _cell_length_c 7.995(4) _cell_angle_alpha 90.00 _cell_angle_beta 95.653(6) _cell_angle_gamma 90.00 _cell_volume 3953(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4420 _cell_measurement_theta_min 2.27 _cell_measurement_theta_max 23.58 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.355 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9706 _exptl_absorpt_correction_T_max 0.9734 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 27118 _diffrn_reflns_av_R_equivalents 0.0692 _diffrn_reflns_av_sigmaI/netI 0.0672 _diffrn_reflns_limit_h_min -42 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6929 _reflns_number_gt 3426 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.8000P)^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 6929 _refine_ls_number_parameters 547 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.3150 _refine_ls_R_factor_gt 0.2648 _refine_ls_wR_factor_ref 0.7801 _refine_ls_wR_factor_gt 0.7374 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.010 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 B1 B 0.4192(3) -0.0503(9) 0.3854(14) 0.044(3) Uani 1 1 d . . . B2 B 0.0807(3) 0.4497(10) 1.1109(17) 0.052(3) Uani 1 1 d . . . C1 C 0.3923(3) -0.2061(9) 0.5120(18) 0.061(3) Uani 1 1 d . . . H1 H 0.4096 -0.2498 0.4768 0.073 Uiso 1 1 calc R . . C2 C 0.3624(4) -0.2299(10) 0.598(2) 0.075(4) Uani 1 1 d . . . H2 H 0.3557 -0.2921 0.6286 0.090 Uiso 1 1 calc R . . C3 C 0.3443(3) -0.1460(9) 0.6299(17) 0.061(3) Uani 1 1 d . . . H3 H 0.3233 -0.1407 0.6878 0.073 Uiso 1 1 calc R . . C4 C 0.3626(3) -0.0716(8) 0.5619(16) 0.054(3) Uani 1 1 d . . . C5 C 0.3568(3) 0.0324(8) 0.5674(14) 0.049(3) Uani 1 1 d . . . C6 C 0.3810(3) 0.0923(8) 0.4931(15) 0.052(3) Uani 1 1 d . . . C7 C 0.3814(3) 0.1953(8) 0.4824(15) 0.057(3) Uani 1 1 d . . . H7 H 0.3643 0.2369 0.5248 0.068 Uiso 1 1 calc R . . C8 C 0.4105(3) 0.2230(9) 0.4011(17) 0.058(3) Uani 1 1 d . . . H8 H 0.4170 0.2860 0.3743 0.070 Uiso 1 1 calc R . . C9 C 0.4297(3) 0.1345(8) 0.3640(14) 0.054(3) Uani 1 1 d . . . C10 C 0.4628(3) 0.1381(9) 0.2793(17) 0.060(3) Uani 1 1 d . . . C11 C 0.4780(3) 0.2207(11) 0.2101(18) 0.070(4) Uani 1 1 d . . . H11 H 0.4683 0.2832 0.2085 0.085 Uiso 1 1 calc R . . C12 C 0.5107(3) 0.1910(10) 0.1436(19) 0.066(4) Uani 1 1 d . . . H12 H 0.5266 0.2305 0.0889 0.080 Uiso 1 1 calc R . . C13 C 0.5150(3) 0.0938(10) 0.1737(15) 0.058(3) Uani 1 1 d . . . C14 C 0.5455(3) 0.0328(13) 0.1400(19) 0.075(4) Uani 1 1 d D . . H14 H 0.5641 0.0576 0.0790 0.089 Uiso 1 1 calc R . . C15 C 0.3238(3) 0.0692(7) 0.6423(13) 0.039(2) Uani 1 1 d . . . C16 C 0.2935(3) 0.1006(8) 0.5371(16) 0.054(3) Uani 1 1 d . . . C17 C 0.2610(3) 0.1246(9) 0.6204(18) 0.062(3) Uani 1 1 d . . . H17 H 0.2393 0.1421 0.5547 0.075 Uiso 1 1 calc R . . C18 C 0.2605(4) 0.1230(9) 0.7905(19) 0.070(4) Uani 1 1 d . . . C19 C 0.2896(3) 0.0900(8) 0.8837(15) 0.050(3) Uani 1 1 d . . . H19 H 0.2870 0.0786 0.9966 0.060 Uiso 1 1 calc R . . C20 C 0.3250(3) 0.0702(8) 0.8263(14) 0.047(3) Uani 1 1 d . . . C21 C 0.2944(4) 0.1075(9) 0.3514(12) 0.057(3) Uani 1 1 d . . . H21A H 0.3067 0.1664 0.3244 0.085 Uiso 1 1 calc R . . H21B H 0.2694 0.1078 0.2978 0.085 Uiso 1 1 calc R . . H21C H 0.3076 0.0528 0.3124 0.085 Uiso 1 1 calc R . . C22 C 0.2251(5) 0.1492(12) 0.871(2) 0.092(5) Uani 1 1 d . . . H22A H 0.2071 0.0982 0.8504 0.138 Uiso 1 1 calc R . . H22B H 0.2151 0.2088 0.8238 0.138 Uiso 1 1 calc R . . H22C H 0.2310 0.1570 0.9902 0.138 Uiso 1 1 calc R . . C23 C 0.3575(3) 0.0359(10) 0.9411(13) 0.058(3) Uani 1 1 d . . . H23A H 0.3533 -0.0299 0.9745 0.087 Uiso 1 1 calc R . . H23B H 0.3605 0.0767 1.0388 0.087 Uiso 1 1 calc R . . H23C H 0.3796 0.0387 0.8836 0.087 Uiso 1 1 calc R . . C24 C 0.1083(4) 0.2962(9) 0.9910(18) 0.069(4) Uani 1 1 d . . . H24 H 0.0914 0.2531 1.0313 0.083 Uiso 1 1 calc R . . C25 C 0.1374(4) 0.2697(9) 0.902(2) 0.076(4) Uani 1 1 d . . . H25 H 0.1433 0.2073 0.8687 0.091 Uiso 1 1 calc R . . C26 C 0.1563(3) 0.3551(8) 0.8709(17) 0.061(3) Uani 1 1 d . . . H26 H 0.1776 0.3605 0.8154 0.073 Uiso 1 1 calc R . . C27 C 0.1368(3) 0.4317(8) 0.9396(14) 0.048(3) Uani 1 1 d . . . C28 C 0.1433(3) 0.5290(8) 0.9431(12) 0.047(3) Uani 1 1 d . . . C29 C 0.1186(3) 0.5915(9) 1.0022(13) 0.048(3) Uani 1 1 d . . . C30 C 0.1180(3) 0.6941(9) 1.0191(16) 0.060(3) Uani 1 1 d . . . H30 H 0.1353 0.7363 0.9794 0.072 Uiso 1 1 calc R . . C31 C 0.0897(4) 0.7207(9) 1.0986(18) 0.067(3) Uani 1 1 d . . . H31 H 0.0837 0.7843 1.1237 0.080 Uiso 1 1 calc R . . C32 C 0.0698(3) 0.6373(7) 1.1403(12) 0.041(2) Uani 1 1 d . . . C33 C 0.0361(3) 0.6390(8) 1.2213(13) 0.045(3) Uani 1 1 d . . . C34 C 0.0214(3) 0.7190(9) 1.2933(17) 0.065(3) Uani 1 1 d . . . H34 H 0.0315 0.7812 1.2985 0.078 Uiso 1 1 calc R . . C35 C -0.0109(4) 0.6902(10) 1.3563(19) 0.075(4) Uani 1 1 d . . . H35 H -0.0269 0.7305 1.4087 0.090 Uiso 1 1 calc R . . C36 C -0.0157(4) 0.5941(10) 1.3301(16) 0.061(3) Uani 1 1 d . . . C37 C -0.0449(4) 0.5280(10) 1.3569(17) 0.072(4) Uani 1 1 d . . . H37 H -0.0636 0.5523 1.4174 0.086 Uiso 1 1 calc R . . C38 C 0.1753(3) 0.5676(7) 0.8553(14) 0.052(3) Uani 1 1 d . . . C39 C 0.2090(3) 0.5955(9) 0.9639(15) 0.062(3) Uani 1 1 d . . . C40 C 0.2382(3) 0.6233(9) 0.8837(15) 0.060(3) Uani 1 1 d . . . H40 H 0.2596 0.6431 0.9490 0.072 Uiso 1 1 calc R . . C41 C 0.2387(4) 0.6249(8) 0.7093(15) 0.057(3) Uani 1 1 d . . . C42 C 0.2029(3) 0.6048(7) 0.6028(12) 0.048(3) Uani 1 1 d . . . H42 H 0.1998 0.6155 0.4875 0.058 Uiso 1 1 calc R . . C43 C 0.1765(3) 0.5708(9) 0.6875(15) 0.057(3) Uani 1 1 d . . . C44 C 0.2125(3) 0.5909(9) 1.1469(17) 0.065(3) Uani 1 1 d . . . H44A H 0.2381 0.5987 1.1894 0.097 Uiso 1 1 calc R . . H44B H 0.2036 0.5291 1.1819 0.097 Uiso 1 1 calc R . . H44C H 0.1979 0.6418 1.1901 0.097 Uiso 1 1 calc R . . C45 C 0.2754(4) 0.6503(11) 0.636(2) 0.079(4) Uani 1 1 d . . . H45A H 0.2849 0.7103 0.6836 0.119 Uiso 1 1 calc R . . H45B H 0.2708 0.6570 0.5162 0.119 Uiso 1 1 calc R . . H45C H 0.2932 0.5995 0.6623 0.119 Uiso 1 1 calc R . . C46 C 0.1427(4) 0.5449(11) 0.5712(17) 0.076(4) Uani 1 1 d . . . H46A H 0.1456 0.5690 0.4606 0.115 Uiso 1 1 calc R . . H46B H 0.1210 0.5736 0.6114 0.115 Uiso 1 1 calc R . . H46C H 0.1399 0.4756 0.5673 0.115 Uiso 1 1 calc R . . F1 F 0.45558(17) -0.0761(5) 0.4456(9) 0.063(2) Uani 1 1 d . . . F2 F 0.4143(2) -0.0713(5) 0.2167(9) 0.064(2) Uani 1 1 d . . . F3 F 0.04461(18) 0.4238(5) 1.0580(9) 0.061(2) Uani 1 1 d . . . F4 F 0.0867(2) 0.4276(5) 1.2815(9) 0.073(2) Uani 1 1 d . . . N1 N 0.3926(3) -0.1075(7) 0.4866(12) 0.052(2) Uani 1 1 d . . . N2 N 0.4121(2) 0.0588(6) 0.4160(12) 0.047(2) Uani 1 1 d . . . N3 N 0.4865(3) 0.0636(8) 0.2537(13) 0.062(3) Uani 1 1 d . . . H3A H 0.4834 0.0046 0.2852 0.074 Uiso 1 1 calc R . . N4 N 0.1076(3) 0.3922(7) 1.0117(12) 0.058(3) Uani 1 1 d . . . N5 N 0.0882(2) 0.5591(6) 1.0838(11) 0.045(2) Uani 1 1 d . . . N6 N 0.0138(3) 0.5624(6) 1.2462(11) 0.048(2) Uani 1 1 d . . . H6 H 0.0174 0.5037 1.2151 0.058 Uiso 1 1 calc R . . O2 O -0.0486(3) 0.4458(8) 1.3121(15) 0.086(3) Uani 1 1 d . . . O1 O 0.5478(3) -0.0531(8) 0.1910(13) 0.076(3) Uani 1 1 d 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 B1 0.052(7) 0.053(7) 0.030(6) 0.019(5) 0.021(5) 0.018(5) B2 0.037(6) 0.062(8) 0.057(8) 0.013(6) 0.007(5) 0.014(5) C1 0.038(6) 0.050(7) 0.097(9) 0.004(6) 0.018(6) 0.008(5) C2 0.067(8) 0.052(7) 0.113(12) 0.022(7) 0.039(8) -0.010(6) C3 0.041(6) 0.067(8) 0.079(8) 0.011(6) 0.022(6) 0.003(5) C4 0.040(6) 0.047(6) 0.074(8) 0.009(5) 0.005(5) -0.004(5) C5 0.034(5) 0.047(6) 0.065(7) -0.018(5) 0.000(5) -0.001(4) C6 0.043(6) 0.047(6) 0.068(7) -0.010(5) 0.017(5) -0.003(5) C7 0.073(7) 0.034(6) 0.068(7) 0.007(5) 0.030(6) 0.004(5) C8 0.051(6) 0.041(6) 0.084(8) 0.004(6) 0.015(6) 0.003(5) C9 0.058(7) 0.051(7) 0.056(7) 0.010(5) 0.020(6) -0.002(5) C10 0.048(6) 0.054(7) 0.078(8) -0.007(6) 0.010(6) -0.004(5) C11 0.032(6) 0.081(9) 0.099(10) 0.015(8) 0.009(6) 0.000(6) C12 0.040(6) 0.070(8) 0.094(9) 0.015(7) 0.030(6) -0.005(6) C13 0.047(6) 0.076(8) 0.053(7) 0.008(6) 0.018(5) 0.007(6) C14 0.035(6) 0.107(12) 0.082(9) -0.001(8) 0.007(6) -0.011(7) C15 0.035(5) 0.031(5) 0.051(6) 0.001(4) 0.001(4) 0.002(4) C16 0.041(6) 0.038(6) 0.077(8) -0.012(5) -0.028(5) 0.002(4) C17 0.045(6) 0.055(7) 0.089(10) 0.002(6) 0.016(6) 0.006(5) C18 0.068(8) 0.053(7) 0.088(10) -0.001(7) 0.004(7) -0.024(6) C19 0.025(5) 0.050(6) 0.074(7) 0.002(5) -0.007(5) -0.007(4) C20 0.051(6) 0.045(6) 0.048(6) 0.020(5) 0.015(5) 0.008(5) C21 0.076(8) 0.066(7) 0.023(5) 0.002(5) -0.021(5) -0.021(6) C22 0.103(12) 0.094(12) 0.083(10) -0.004(8) 0.027(9) 0.018(9) C23 0.054(7) 0.080(8) 0.037(6) 0.009(5) -0.005(5) 0.019(6) C24 0.082(9) 0.049(7) 0.078(9) 0.016(6) 0.019(7) 0.004(6) C25 0.082(9) 0.036(6) 0.111(12) -0.009(7) 0.023(8) 0.003(6) C26 0.062(7) 0.045(7) 0.076(8) -0.010(5) 0.013(6) -0.001(5) C27 0.051(6) 0.051(6) 0.044(6) -0.006(5) 0.008(5) -0.006(5) C28 0.054(6) 0.055(7) 0.035(5) -0.029(5) 0.021(5) -0.015(5) C29 0.040(6) 0.063(7) 0.040(6) -0.010(5) 0.003(4) -0.004(5) C30 0.041(6) 0.056(7) 0.083(9) 0.004(6) 0.006(6) -0.005(5) C31 0.074(8) 0.045(7) 0.086(9) -0.002(6) 0.026(7) -0.005(6) C32 0.040(5) 0.047(6) 0.038(5) -0.006(4) 0.009(4) -0.001(4) C33 0.046(6) 0.047(6) 0.042(6) -0.016(4) 0.005(5) -0.002(4) C34 0.068(8) 0.048(7) 0.082(9) -0.027(6) 0.023(7) 0.002(6) C35 0.089(9) 0.062(8) 0.079(9) -0.010(7) 0.032(7) 0.006(7) C36 0.064(7) 0.063(8) 0.055(7) -0.006(6) 0.001(6) 0.005(6) C37 0.101(10) 0.051(8) 0.072(8) 0.003(6) 0.048(8) -0.014(7) C38 0.070(7) 0.039(6) 0.050(6) -0.005(5) 0.020(6) -0.001(5) C39 0.059(7) 0.071(8) 0.059(7) -0.029(6) 0.028(6) -0.003(6) C40 0.049(6) 0.072(8) 0.057(7) 0.002(6) -0.005(5) -0.019(6) C41 0.072(8) 0.046(6) 0.057(7) -0.001(5) 0.032(6) -0.021(5) C42 0.072(7) 0.040(6) 0.038(5) 0.002(4) 0.033(5) 0.017(5) C43 0.057(7) 0.066(8) 0.050(7) 0.004(5) 0.018(6) 0.010(6) C44 0.054(7) 0.051(7) 0.091(9) 0.008(6) 0.016(6) 0.012(6) C45 0.056(8) 0.090(10) 0.099(11) 0.018(8) 0.041(8) -0.009(7) C46 0.096(11) 0.078(9) 0.059(8) -0.010(7) 0.026(7) 0.006(8) F1 0.044(4) 0.066(4) 0.077(5) 0.016(3) 0.002(3) 0.009(3) F2 0.078(5) 0.062(4) 0.054(4) -0.009(3) 0.019(4) 0.003(3) F3 0.059(4) 0.046(4) 0.081(5) -0.017(3) 0.023(4) -0.008(3) F4 0.106(6) 0.066(5) 0.048(4) -0.004(3) 0.015(4) 0.002(4) N1 0.049(5) 0.046(5) 0.064(6) 0.000(4) 0.015(4) 0.005(4) N2 0.040(5) 0.041(5) 0.059(5) -0.003(4) 0.002(4) 0.001(4) N3 0.046(5) 0.086(8) 0.056(6) 0.018(5) 0.021(5) -0.003(5) N4 0.063(6) 0.053(6) 0.059(6) 0.003(5) 0.014(5) -0.004(5) N5 0.046(5) 0.049(5) 0.044(5) -0.002(4) 0.023(4) -0.001(4) N6 0.056(5) 0.040(5) 0.049(5) 0.007(4) 0.011(4) 0.004(4) O2 0.086(7) 0.072(7) 0.106(8) -0.001(6) 0.032(6) 0.001(5) O1 0.071(6) 0.073(7) 0.086(7) 0.000(5) 0.019(5) 0.014(5) _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 B1 F2 1.374(13) . ? B1 F1 1.398(13) . ? B1 N1 1.533(14) . ? B1 N2 1.548(14) . ? B2 F3 1.377(14) . ? B2 F4 1.394(15) . ? B2 N4 1.532(15) . ? B2 N5 1.548(16) . ? C1 N1 1.372(15) . ? C1 C2 1.376(16) . ? C1 H1 0.9300 . ? C2 C3 1.363(18) . ? C2 H2 0.9300 . ? C3 C4 1.361(15) . ? C3 H3 0.9300 . ? C4 N1 1.383(14) . ? C4 C5 1.448(15) . ? C5 C6 1.377(15) . ? C5 C15 1.473(14) . ? C6 N2 1.411(13) . ? C6 C7 1.421(16) . ? C7 C8 1.344(16) . ? C7 H7 0.9300 . ? C8 C9 1.446(16) . ? C8 H8 0.9300 . ? C9 N2 1.308(13) . ? C9 C10 1.432(16) . ? C10 N3 1.363(15) . ? C10 C11 1.400(17) . ? C11 C12 1.402(16) . ? C11 H11 0.9300 . ? C12 C13 1.367(18) . ? C12 H12 0.9300 . ? C13 N3 1.333(14) . ? C13 C14 1.431(18) . ? C14 O1 1.251(18) . ? C14 H14 0.9300 . ? C15 C16 1.382(14) . ? C15 C20 1.468(15) . ? C16 C17 1.443(16) . ? C16 C21 1.491(16) . ? C17 C18 1.362(19) . ? C17 H17 0.9300 . ? C18 C19 1.307(17) . ? C18 C22 1.530(19) . ? C19 C20 1.426(15) . ? C19 H19 0.9300 . ? C20 C23 1.494(15) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 N4 1.333(16) . ? C24 C25 1.377(18) . ? C24 H24 0.9300 . ? C25 C26 1.392(17) . ? C25 H25 0.9300 . ? C26 C27 1.408(15) . ? C26 H26 0.9300 . ? C27 C28 1.359(15) . ? C27 N4 1.365(14) . ? C28 C29 1.356(15) . ? C28 C38 1.508(14) . ? C29 N5 1.405(13) . ? C29 C30 1.420(17) . ? C30 C31 1.308(17) . ? C30 H30 0.9300 . ? C31 C32 1.412(16) . ? C31 H31 0.9300 . ? C32 N5 1.366(12) . ? C32 C33 1.434(14) . ? C33 N6 1.351(14) . ? C33 C34 1.373(15) . ? C34 C35 1.372(18) . ? C34 H34 0.9300 . ? C35 C36 1.348(19) . ? C35 H35 0.9300 . ? C36 N6 1.385(15) . ? C36 C37 1.425(18) . ? C37 O2 1.190(16) . ? C37 H37 0.9300 . ? C38 C43 1.347(16) . ? C38 C39 1.474(17) . ? C39 C40 1.340(16) . ? C39 C44 1.458(18) . ? C40 C41 1.396(17) . ? C40 H40 0.9300 . ? C41 C42 1.502(17) . ? C41 C45 1.539(15) . ? C42 C43 1.310(15) . ? C42 H42 0.9300 . ? C43 C46 1.500(18) . ? C44 H44A 0.9600 . ? C44 H44B 0.9600 . ? C44 H44C 0.9600 . ? C45 H45A 0.9600 . ? C45 H45B 0.9600 . ? C45 H45C 0.9600 . ? C46 H46A 0.9600 . ? C46 H46B 0.9600 . ? C46 H46C 0.9600 . ? N3 H3A 0.8600 . ? N6 H6 0.8600 . ? 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 F2 B1 F1 108.2(8) . . ? F2 B1 N1 112.5(10) . . ? F1 B1 N1 107.7(8) . . ? F2 B1 N2 110.6(8) . . ? F1 B1 N2 110.9(10) . . ? N1 B1 N2 107.0(8) . . ? F3 B2 F4 107.1(10) . . ? F3 B2 N4 109.6(10) . . ? F4 B2 N4 110.4(9) . . ? F3 B2 N5 112.4(9) . . ? F4 B2 N5 109.7(10) . . ? N4 B2 N5 107.6(9) . . ? N1 C1 C2 109.1(10) . . ? N1 C1 H1 125.4 . . ? C2 C1 H1 125.4 . . ? C3 C2 C1 107.8(11) . . ? C3 C2 H2 126.1 . . ? C1 C2 H2 126.1 . . ? C4 C3 C2 107.7(10) . . ? C4 C3 H3 126.2 . . ? C2 C3 H3 126.2 . . ? C3 C4 N1 109.6(10) . . ? C3 C4 C5 131.0(11) . . ? N1 C4 C5 119.3(9) . . ? C6 C5 C4 118.6(10) . . ? C6 C5 C15 122.8(10) . . ? C4 C5 C15 118.5(9) . . ? C5 C6 N2 124.0(10) . . ? C5 C6 C7 129.4(10) . . ? N2 C6 C7 106.6(9) . . ? C8 C7 C6 109.0(10) . . ? C8 C7 H7 125.5 . . ? C6 C7 H7 125.5 . . ? C7 C8 C9 105.8(10) . . ? C7 C8 H8 127.1 . . ? C9 C8 H8 127.1 . . ? N2 C9 C10 129.1(11) . . ? N2 C9 C8 110.5(10) . . ? C10 C9 C8 120.4(10) . . ? N3 C10 C11 106.1(11) . . ? N3 C10 C9 127.5(11) . . ? C11 C10 C9 126.4(11) . . ? C10 C11 C12 106.9(12) . . ? C10 C11 H11 126.5 . . ? C12 C11 H11 126.6 . . ? C13 C12 C11 107.7(10) . . ? C13 C12 H12 126.1 . . ? C11 C12 H12 126.1 . . ? N3 C13 C12 108.0(10) . . ? N3 C13 C14 123.6(13) . . ? C12 C13 C14 128.2(11) . . ? O1 C14 C13 121.4(12) . . ? O1 C14 H14 119.3 . . ? C13 C14 H14 119.3 . . ? C16 C15 C20 123.3(10) . . ? C16 C15 C5 118.8(10) . . ? C20 C15 C5 117.8(9) . . ? C15 C16 C17 114.9(11) . . ? C15 C16 C21 122.2(11) . . ? C17 C16 C21 122.9(10) . . ? C18 C17 C16 123.3(12) . . ? C18 C17 H17 118.4 . . ? C16 C17 H17 118.3 . . ? C19 C18 C17 119.0(13) . . ? C19 C18 C22 119.9(13) . . ? C17 C18 C22 120.8(13) . . ? C18 C19 C20 125.3(12) . . ? C18 C19 H19 117.4 . . ? C20 C19 H19 117.4 . . ? C19 C20 C15 112.7(10) . . ? C19 C20 C23 122.5(10) . . ? C15 C20 C23 123.8(9) . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C18 C22 H22A 109.5 . . ? C18 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C18 C22 H22C 109.4 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C20 C23 H23A 109.5 . . ? C20 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C20 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? N4 C24 C25 110.7(11) . . ? N4 C24 H24 124.7 . . ? C25 C24 H24 124.7 . . ? C24 C25 C26 106.2(11) . . ? C24 C25 H25 126.9 . . ? C26 C25 H25 126.9 . . ? C25 C26 C27 107.0(11) . . ? C25 C26 H26 126.5 . . ? C27 C26 H26 126.5 . . ? C28 C27 N4 121.5(10) . . ? C28 C27 C26 131.0(10) . . ? N4 C27 C26 107.6(10) . . ? C29 C28 C27 121.1(10) . . ? C29 C28 C38 119.9(10) . . ? C27 C28 C38 118.4(9) . . ? C28 C29 N5 122.0(11) . . ? C28 C29 C30 133.0(10) . . ? N5 C29 C30 104.6(9) . . ? C31 C30 C29 110.1(10) . . ? C31 C30 H30 124.9 . . ? C29 C30 H30 124.9 . . ? C30 C31 C32 109.2(11) . . ? C30 C31 H31 125.4 . . ? C32 C31 H31 125.4 . . ? N5 C32 C31 106.7(9) . . ? N5 C32 C33 128.6(9) . . ? C31 C32 C33 124.7(10) . . ? N6 C33 C34 107.8(10) . . ? N6 C33 C32 126.6(9) . . ? C34 C33 C32 125.5(11) . . ? C33 C34 C35 107.3(11) . . ? C33 C34 H34 126.3 . . ? C35 C34 H34 126.3 . . ? C36 C35 C34 109.2(11) . . ? C36 C35 H35 125.4 . . ? C34 C35 H35 125.4 . . ? C35 C36 N6 106.9(11) . . ? C35 C36 C37 133.6(12) . . ? N6 C36 C37 119.2(11) . . ? O2 C37 C36 128.6(13) . . ? O2 C37 H37 115.7 . . ? C36 C37 H37 115.7 . . ? C43 C38 C39 118.3(11) . . ? C43 C38 C28 125.1(11) . . ? C39 C38 C28 116.4(9) . . ? C40 C39 C44 120.0(11) . . ? C40 C39 C38 115.7(11) . . ? C44 C39 C38 124.3(10) . . ? C39 C40 C41 124.9(11) . . ? C39 C40 H40 117.6 . . ? C41 C40 H40 117.5 . . ? C40 C41 C42 117.8(10) . . ? C40 C41 C45 118.8(12) . . ? C42 C41 C45 123.4(10) . . ? C43 C42 C41 113.8(10) . . ? C43 C42 H42 123.1 . . ? C41 C42 H42 123.1 . . ? C42 C43 C38 128.4(13) . . ? C42 C43 C46 110.7(11) . . ? C38 C43 C46 120.5(11) . . ? C39 C44 H44A 109.5 . . ? C39 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C39 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? C41 C45 H45A 109.5 . . ? C41 C45 H45B 109.5 . . ? H45A C45 H45B 109.5 . . ? C41 C45 H45C 109.5 . . ? H45A C45 H45C 109.5 . . ? H45B C45 H45C 109.5 . . ? C43 C46 H46A 109.5 . . ? C43 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? C43 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? C1 N1 C4 105.8(9) . . ? C1 N1 B1 126.9(9) . . ? C4 N1 B1 127.2(9) . . ? C9 N2 C6 108.1(9) . . ? C9 N2 B1 129.0(9) . . ? C6 N2 B1 122.5(9) . . ? C13 N3 C10 111.3(11) . . ? C13 N3 H3A 124.4 . . ? C10 N3 H3A 124.4 . . ? C24 N4 C27 108.5(10) . . ? C24 N4 B2 126.7(10) . . ? C27 N4 B2 124.6(10) . . ? C32 N5 C29 109.3(9) . . ? C32 N5 B2 128.6(8) . . ? C29 N5 B2 121.9(9) . . ? C33 N6 C36 108.8(9) . . ? C33 N6 H6 125.6 . . ? C36 N6 H6 125.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -1.4(17) . . . . ? C1 C2 C3 C4 1.0(18) . . . . ? C2 C3 C4 N1 -0.3(16) . . . . ? C2 C3 C4 C5 -175.8(13) . . . . ? C3 C4 C5 C6 176.8(13) . . . . ? N1 C4 C5 C6 1.7(17) . . . . ? C3 C4 C5 C15 -7.2(19) . . . . ? N1 C4 C5 C15 177.7(10) . . . . ? C4 C5 C6 N2 -2.2(17) . . . . ? C15 C5 C6 N2 -178.0(10) . . . . ? C4 C5 C6 C7 -179.6(12) . . . . ? C15 C5 C6 C7 4.6(19) . . . . ? C5 C6 C7 C8 178.9(12) . . . . ? N2 C6 C7 C8 1.1(14) . . . . ? C6 C7 C8 C9 -1.7(14) . . . . ? C7 C8 C9 N2 1.8(15) . . . . ? C7 C8 C9 C10 -178.9(11) . . . . ? N2 C9 C10 N3 -10(2) . . . . ? C8 C9 C10 N3 171.2(12) . . . . ? N2 C9 C10 C11 172.4(13) . . . . ? C8 C9 C10 C11 -7(2) . . . . ? N3 C10 C11 C12 0.4(15) . . . . ? C9 C10 C11 C12 178.7(13) . . . . ? C10 C11 C12 C13 -0.5(16) . . . . ? C11 C12 C13 N3 0.4(15) . . . . ? C11 C12 C13 C14 -175.1(14) . . . . ? N3 C13 C14 O1 -3(2) . . . . ? C12 C13 C14 O1 172.0(14) . . . . ? C6 C5 C15 C16 73.1(14) . . . . ? C4 C5 C15 C16 -102.7(12) . . . . ? C6 C5 C15 C20 -107.0(13) . . . . ? C4 C5 C15 C20 77.2(12) . . . . ? C20 C15 C16 C17 -6.8(15) . . . . ? C5 C15 C16 C17 173.1(9) . . . . ? C20 C15 C16 C21 174.1(10) . . . . ? C5 C15 C16 C21 -6.0(15) . . . . ? C15 C16 C17 C18 4.2(17) . . . . ? C21 C16 C17 C18 -176.8(12) . . . . ? C16 C17 C18 C19 -6.3(19) . . . . ? C16 C17 C18 C22 -180.0(12) . . . . ? C17 C18 C19 C20 11.3(19) . . . . ? C22 C18 C19 C20 -174.9(12) . . . . ? C18 C19 C20 C15 -13.1(16) . . . . ? C18 C19 C20 C23 177.8(12) . . . . ? C16 C15 C20 C19 10.7(15) . . . . ? C5 C15 C20 C19 -169.2(9) . . . . ? C16 C15 C20 C23 179.6(11) . . . . ? C5 C15 C20 C23 -0.3(16) . . . . ? N4 C24 C25 C26 1.9(17) . . . . ? C24 C25 C26 C27 -1.7(17) . . . . ? C25 C26 C27 C28 -179.5(13) . . . . ? C25 C26 C27 N4 0.9(15) . . . . ? N4 C27 C28 C29 -7.2(18) . . . . ? C26 C27 C28 C29 173.3(12) . . . . ? N4 C27 C28 C38 -177.8(10) . . . . ? C26 C27 C28 C38 2.7(19) . . . . ? C27 C28 C29 N5 9.1(17) . . . . ? C38 C28 C29 N5 179.6(9) . . . . ? C27 C28 C29 C30 -179.5(12) . . . . ? C38 C28 C29 C30 -9.0(19) . . . . ? C28 C29 C30 C31 -173.9(13) . . . . ? N5 C29 C30 C31 -1.4(13) . . . . ? C29 C30 C31 C32 0.3(16) . . . . ? C30 C31 C32 N5 1.0(15) . . . . ? C30 C31 C32 C33 -177.0(11) . . . . ? N5 C32 C33 N6 -5.7(18) . . . . ? C31 C32 C33 N6 171.9(11) . . . . ? N5 C32 C33 C34 171.6(12) . . . . ? C31 C32 C33 C34 -10.8(19) . . . . ? N6 C33 C34 C35 -2.4(15) . . . . ? C32 C33 C34 C35 179.9(12) . . . . ? C33 C34 C35 C36 2.1(17) . . . . ? C34 C35 C36 N6 -1.1(16) . . . . ? C34 C35 C36 C37 -174.5(15) . . . . ? C35 C36 C37 O2 170.6(17) . . . . ? N6 C36 C37 O2 -2(2) . . . . ? C29 C28 C38 C43 -100.2(13) . . . . ? C27 C28 C38 C43 70.6(16) . . . . ? C29 C28 C38 C39 85.6(13) . . . . ? C27 C28 C38 C39 -103.7(12) . . . . ? C43 C38 C39 C40 0.9(17) . . . . ? C28 C38 C39 C40 175.6(11) . . . . ? C43 C38 C39 C44 -176.8(11) . . . . ? C28 C38 C39 C44 -2.1(17) . . . . ? C44 C39 C40 C41 176.0(12) . . . . ? C38 C39 C40 C41 -2(2) . . . . ? C39 C40 C41 C42 7(2) . . . . ? C39 C40 C41 C45 -174.8(13) . . . . ? C40 C41 C42 C43 -11.6(16) . . . . ? C45 C41 C42 C43 170.5(11) . . . . ? C41 C42 C43 C38 12.3(18) . . . . ? C41 C42 C43 C46 -175.4(10) . . . . ? C39 C38 C43 C42 -7.2(19) . . . . ? C28 C38 C43 C42 178.6(11) . . . . ? C39 C38 C43 C46 -178.9(11) . . . . ? C28 C38 C43 C46 7.0(18) . . . . ? C2 C1 N1 C4 1.1(14) . . . . ? C2 C1 N1 B1 -175.2(12) . . . . ? C3 C4 N1 C1 -0.5(14) . . . . ? C5 C4 N1 C1 175.6(11) . . . . ? C3 C4 N1 B1 175.8(11) . . . . ? C5 C4 N1 B1 -8.2(18) . . . . ? F2 B1 N1 C1 66.6(14) . . . . ? F1 B1 N1 C1 -52.5(15) . . . . ? N2 B1 N1 C1 -171.8(11) . . . . ? F2 B1 N1 C4 -109.0(12) . . . . ? F1 B1 N1 C4 131.9(11) . . . . ? N2 B1 N1 C4 12.7(15) . . . . ? C10 C9 N2 C6 179.7(12) . . . . ? C8 C9 N2 C6 -1.1(14) . . . . ? C10 C9 N2 B1 -7(2) . . . . ? C8 C9 N2 B1 171.8(10) . . . . ? C5 C6 N2 C9 -177.8(11) . . . . ? C7 C6 N2 C9 0.1(13) . . . . ? C5 C6 N2 B1 8.7(17) . . . . ? C7 C6 N2 B1 -173.4(10) . . . . ? F2 B1 N2 C9 -61.6(15) . . . . ? F1 B1 N2 C9 58.4(14) . . . . ? N1 B1 N2 C9 175.6(11) . . . . ? F2 B1 N2 C6 110.5(11) . . . . ? F1 B1 N2 C6 -129.5(10) . . . . ? N1 B1 N2 C6 -12.4(14) . . . . ? C12 C13 N3 C10 -0.2(15) . . . . ? C14 C13 N3 C10 175.6(13) . . . . ? C11 C10 N3 C13 -0.2(15) . . . . ? C9 C10 N3 C13 -178.4(12) . . . . ? C25 C24 N4 C27 -1.3(15) . . . . ? C25 C24 N4 B2 -176.9(12) . . . . ? C28 C27 N4 C24 -179.4(11) . . . . ? C26 C27 N4 C24 0.2(14) . . . . ? C28 C27 N4 B2 -3.7(18) . . . . ? C26 C27 N4 B2 175.9(11) . . . . ? F3 B2 N4 C24 -51.9(16) . . . . ? F4 B2 N4 C24 65.9(16) . . . . ? N5 B2 N4 C24 -174.4(11) . . . . ? F3 B2 N4 C27 133.3(11) . . . . ? F4 B2 N4 C27 -109.0(13) . . . . ? N5 B2 N4 C27 10.8(15) . . . . ? C31 C32 N5 C29 -1.9(13) . . . . ? C33 C32 N5 C29 175.9(10) . . . . ? C31 C32 N5 B2 173.5(11) . . . . ? C33 C32 N5 B2 -8.6(18) . . . . ? C28 C29 N5 C32 175.6(10) . . . . ? C30 C29 N5 C32 2.1(11) . . . . ? C28 C29 N5 B2 -0.2(16) . . . . ? C30 C29 N5 B2 -173.7(10) . . . . ? F3 B2 N5 C32 55.6(15) . . . . ? F4 B2 N5 C32 -63.4(14) . . . . ? N4 B2 N5 C32 176.4(10) . . . . ? F3 B2 N5 C29 -129.4(10) . . . . ? F4 B2 N5 C29 111.5(11) . . . . ? N4 B2 N5 C29 -8.7(14) . . . . ? C34 C33 N6 C36 1.7(13) . . . . ? C32 C33 N6 C36 179.4(10) . . . . ? C35 C36 N6 C33 -0.4(14) . . . . ? C37 C36 N6 C33 174.2(12) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.812 _refine_diff_density_min -0.923 _refine_diff_density_rms 0.168 # Attachment 'BODIPY-7.cif' data_110728a_0m _database_code_depnum_ccdc_archive 'CCDC 863481' #TrackingRef 'BODIPY-7.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C44 H42 N6' _chemical_formula_weight 654.84 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.481(6) _cell_length_b 12.320(8) _cell_length_c 17.351(11) _cell_angle_alpha 70.679(8) _cell_angle_beta 80.779(9) _cell_angle_gamma 83.598(9) _cell_volume 1884(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1981 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 20.37 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.154 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9783 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 6530 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.1029 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 6530 _reflns_number_gt 3304 _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^)+(0.4100P)^2^+0.2500P] 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 6530 _refine_ls_number_parameters 457 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2280 _refine_ls_R_factor_gt 0.1705 _refine_ls_wR_factor_ref 0.5599 _refine_ls_wR_factor_gt 0.5341 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _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 C1 C 0.8574(10) 0.4892(7) 0.3162(6) 0.057(2) Uani 1 1 d . . . H1 H 0.8319 0.4355 0.2946 0.069 Uiso 1 1 calc R . . C2 C 0.9359(10) 0.4670(8) 0.3797(6) 0.067(3) Uani 1 1 d . . . H2 H 0.9721 0.3947 0.4097 0.080 Uiso 1 1 calc R . . C3 C 0.9528(10) 0.5684(7) 0.3920(5) 0.057(2) Uani 1 1 d . . . H3 H 1.0040 0.5766 0.4309 0.068 Uiso 1 1 calc R . . C4 C 0.8811(8) 0.6572(7) 0.3368(5) 0.0424(18) Uani 1 1 d . . . C5 C 0.8637(8) 0.7762(6) 0.3279(4) 0.0396(17) Uani 1 1 d . . . C6 C 0.9487(9) 0.8122(7) 0.3819(5) 0.0467(19) Uani 1 1 d . . . C7 C 0.8818(10) 0.8172(7) 0.4580(5) 0.056(2) Uani 1 1 d . . . C8 C 0.9697(15) 0.8422(9) 0.5084(7) 0.079(3) Uani 1 1 d . . . H8 H 0.9279 0.8473 0.5594 0.095 Uiso 1 1 calc R . . C9 C 1.1104(15) 0.8587(9) 0.4860(8) 0.081(3) Uani 1 1 d . . . C10 C 1.1686(12) 0.8559(9) 0.4081(8) 0.082(3) Uani 1 1 d . . . H10 H 1.2646 0.8707 0.3906 0.099 Uiso 1 1 calc R . . C11 C 1.0915(9) 0.8324(7) 0.3551(6) 0.056(2) Uani 1 1 d . . . C12 C 0.7258(12) 0.7998(10) 0.4869(6) 0.080(3) Uani 1 1 d . . . H12A H 0.7076 0.7213 0.4953 0.121 Uiso 1 1 calc R . . H12B H 0.6702 0.8505 0.4461 0.121 Uiso 1 1 calc R . . H12C H 0.6996 0.8165 0.5377 0.121 Uiso 1 1 calc R . . C13 C 1.2049(17) 0.8813(13) 0.5404(11) 0.145(8) Uani 1 1 d . . . H13A H 1.2323 0.9595 0.5178 0.218 Uiso 1 1 calc R . . H13B H 1.2891 0.8297 0.5434 0.218 Uiso 1 1 calc R . . H13C H 1.1536 0.8692 0.5946 0.218 Uiso 1 1 calc R . . C14 C 1.1625(11) 0.8249(10) 0.2730(7) 0.075(3) Uani 1 1 d . . . H14A H 1.1769 0.7456 0.2754 0.112 Uiso 1 1 calc R . . H14B H 1.2533 0.8588 0.2597 0.112 Uiso 1 1 calc R . . H14C H 1.1027 0.8656 0.2314 0.112 Uiso 1 1 calc R . . C15 C 0.7756(8) 0.8573(7) 0.2800(5) 0.049(2) Uani 1 1 d . . . C16 C 0.7563(9) 0.9768(7) 0.2735(5) 0.053(2) Uani 1 1 d . . . H16 H 0.8035 1.0148 0.2991 0.064 Uiso 1 1 calc R . . C17 C 0.6558(10) 1.0233(7) 0.2226(6) 0.057(2) Uani 1 1 d . . . H17 H 0.6212 1.1000 0.2066 0.068 Uiso 1 1 calc R . . C18 C 0.6129(9) 0.9350(7) 0.1982(5) 0.049(2) Uani 1 1 d . . . C19 C 0.5069(9) 0.9465(7) 0.1466(5) 0.052(2) Uani 1 1 d . . . C20 C 0.4134(9) 1.0395(8) 0.1126(6) 0.063(2) Uani 1 1 d . . . H20 H 0.4086 1.1121 0.1186 0.075 Uiso 1 1 calc R . . C21 C 0.3300(10) 1.0048(9) 0.0689(6) 0.069(3) Uani 1 1 d . . . H21 H 0.2577 1.0501 0.0405 0.082 Uiso 1 1 calc R . . C22 C 0.3694(9) 0.8937(9) 0.0735(5) 0.061(2) Uani 1 1 d . . . H22 H 0.3305 0.8498 0.0487 0.074 Uiso 1 1 calc R . . C23 C 0.4494(10) 0.6463(9) 0.3836(6) 0.065(3) Uani 1 1 d . . . H23 H 0.4815 0.6982 0.4046 0.078 Uiso 1 1 calc R . . C24 C 0.3494(11) 0.5652(9) 0.4241(6) 0.071(3) Uani 1 1 d . . . H24 H 0.3022 0.5523 0.4773 0.085 Uiso 1 1 calc R . . C25 C 0.3331(9) 0.5075(8) 0.3712(5) 0.058(2) Uani 1 1 d . . . H25 H 0.2718 0.4487 0.3823 0.070 Uiso 1 1 calc R . . C26 C 0.4223(9) 0.5507(7) 0.2989(5) 0.050(2) Uani 1 1 d . . . C27 C 0.4516(8) 0.5096(7) 0.2290(5) 0.0481(19) Uani 1 1 d . . . C28 C 0.3577(9) 0.4173(7) 0.2312(5) 0.051(2) Uani 1 1 d . . . C29 C 0.2286(9) 0.4482(7) 0.1983(5) 0.054(2) Uani 1 1 d . . . C30 C 0.1436(9) 0.3598(8) 0.2033(5) 0.055(2) Uani 1 1 d . . . H30 H 0.0575 0.3793 0.1813 0.066 Uiso 1 1 calc R . . C31 C 0.1815(10) 0.2463(8) 0.2390(6) 0.060(2) Uani 1 1 d . . . C32 C 0.3075(11) 0.2175(8) 0.2714(6) 0.068(3) Uani 1 1 d . . . H32 H 0.3335 0.1401 0.2962 0.081 Uiso 1 1 calc R . . C33 C 0.3996(10) 0.3011(8) 0.2685(5) 0.058(2) Uani 1 1 d . . . C34 C 0.1791(12) 0.5725(9) 0.1596(7) 0.075(3) Uani 1 1 d . . . H34A H 0.1604 0.6101 0.2009 0.112 Uiso 1 1 calc R . . H34B H 0.0932 0.5760 0.1359 0.112 Uiso 1 1 calc R . . H34C H 0.2524 0.6105 0.1172 0.112 Uiso 1 1 calc R . . C35 C 0.0843(12) 0.1547(9) 0.2423(8) 0.085(3) Uani 1 1 d . . . H35A H -0.0040 0.1619 0.2765 0.128 Uiso 1 1 calc R . . H35B H 0.1304 0.0797 0.2647 0.128 Uiso 1 1 calc R . . H35C H 0.0651 0.1643 0.1877 0.128 Uiso 1 1 calc R . . C36 C 0.5365(12) 0.2681(9) 0.3059(7) 0.080(3) Uani 1 1 d . . . H36A H 0.5285 0.1954 0.3491 0.120 Uiso 1 1 calc R . . H36B H 0.5546 0.3260 0.3283 0.120 Uiso 1 1 calc R . . H36C H 0.6141 0.2617 0.2644 0.120 Uiso 1 1 calc R . . C37 C 0.5537(9) 0.5440(7) 0.1619(5) 0.051(2) Uani 1 1 d . . . C38 C 0.5859(10) 0.4992(9) 0.0944(6) 0.067(3) Uani 1 1 d . . . H38 H 0.5387 0.4425 0.0861 0.081 Uiso 1 1 calc R . . C39 C 0.6979(11) 0.5551(9) 0.0452(6) 0.072(3) Uani 1 1 d . . . H39 H 0.7417 0.5449 -0.0041 0.087 Uiso 1 1 calc R . . C40 C 0.7372(8) 0.6326(8) 0.0821(5) 0.053(2) Uani 1 1 d . . . C41 C 0.8504(9) 0.7092(8) 0.0507(5) 0.053(2) Uani 1 1 d . . . C42 C 0.9551(10) 0.7248(10) -0.0161(6) 0.071(3) Uani 1 1 d . . . H42 H 0.9656 0.6858 -0.0545 0.086 Uiso 1 1 calc R . . C43 C 1.0415(10) 0.8074(10) -0.0166(6) 0.073(3) Uani 1 1 d . . . H43 H 1.1215 0.8326 -0.0547 0.088 Uiso 1 1 calc R . . C44 C 0.9915(9) 0.8456(8) 0.0470(6) 0.062(2) Uani 1 1 d . . . H44 H 1.0285 0.9030 0.0603 0.075 Uiso 1 1 calc R . . N1 N 0.8237(7) 0.6038(5) 0.2904(4) 0.0475(16) Uani 1 1 d . . . H1A H 0.7739 0.6390 0.2510 0.057 Uiso 1 1 calc R . . N2 N 0.6867(7) 0.8348(6) 0.2316(4) 0.0457(16) Uani 1 1 d . . . N3 N 0.4762(8) 0.8593(6) 0.1212(4) 0.0557(19) Uani 1 1 d . . . H3A H 0.5188 0.7916 0.1338 0.067 Uiso 1 1 calc R . . N4 N 0.4910(7) 0.6360(6) 0.3085(4) 0.0518(18) Uani 1 1 d . . . H4 H 0.5524 0.6774 0.2716 0.062 Uiso 1 1 calc R . . N5 N 0.6501(7) 0.6292(6) 0.1516(4) 0.0491(17) Uani 1 1 d . . . N6 N 0.8753(7) 0.7841(6) 0.0887(4) 0.0544(18) Uani 1 1 d . . . H6 H 0.8253 0.7919 0.1328 0.065 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 C1 0.063(5) 0.042(5) 0.067(6) -0.018(4) -0.012(4) 0.000(4) C2 0.067(6) 0.052(6) 0.076(6) -0.014(5) -0.013(5) 0.005(5) C3 0.070(6) 0.050(5) 0.046(5) -0.006(4) -0.014(4) -0.009(4) C4 0.040(4) 0.042(4) 0.053(4) -0.023(4) -0.012(3) -0.004(3) C5 0.045(4) 0.037(4) 0.037(4) -0.010(3) -0.011(3) -0.002(3) C6 0.054(5) 0.046(5) 0.043(4) -0.018(3) -0.014(4) 0.003(4) C7 0.074(6) 0.043(5) 0.053(5) -0.016(4) -0.015(4) 0.002(4) C8 0.116(10) 0.060(7) 0.073(7) -0.030(5) -0.038(7) 0.007(6) C9 0.112(10) 0.060(7) 0.094(8) -0.045(6) -0.051(7) 0.016(6) C10 0.071(7) 0.058(6) 0.123(10) -0.018(6) -0.047(7) -0.009(5) C11 0.063(6) 0.039(5) 0.081(6) -0.030(4) -0.031(5) 0.002(4) C12 0.099(8) 0.081(8) 0.054(6) -0.017(5) 0.003(5) -0.009(6) C13 0.166(14) 0.125(12) 0.216(18) -0.109(13) -0.156(14) 0.055(11) C14 0.061(6) 0.088(8) 0.078(7) -0.031(6) -0.002(5) -0.014(5) C15 0.046(4) 0.044(5) 0.061(5) -0.021(4) -0.009(4) -0.007(4) C16 0.062(5) 0.044(5) 0.057(5) -0.017(4) -0.015(4) -0.001(4) C17 0.066(5) 0.041(5) 0.066(6) -0.018(4) -0.014(4) -0.002(4) C18 0.054(5) 0.042(5) 0.050(5) -0.014(4) -0.012(4) 0.003(4) C19 0.048(5) 0.048(5) 0.057(5) -0.012(4) -0.010(4) -0.003(4) C20 0.051(5) 0.063(6) 0.064(6) -0.005(5) -0.016(4) 0.004(4) C21 0.062(6) 0.073(7) 0.063(6) -0.008(5) -0.016(5) -0.001(5) C22 0.058(5) 0.071(7) 0.052(5) -0.010(4) -0.019(4) -0.007(5) C23 0.064(6) 0.081(7) 0.056(5) -0.028(5) -0.010(4) -0.007(5) C24 0.079(7) 0.080(7) 0.050(5) -0.023(5) 0.013(5) -0.018(5) C25 0.064(5) 0.058(6) 0.059(5) -0.030(4) 0.006(4) -0.013(4) C26 0.056(5) 0.046(5) 0.047(5) -0.011(4) -0.009(4) -0.008(4) C27 0.047(4) 0.045(5) 0.054(5) -0.018(4) -0.011(4) -0.002(4) C28 0.054(5) 0.048(5) 0.055(5) -0.019(4) -0.008(4) -0.007(4) C29 0.057(5) 0.047(5) 0.060(5) -0.019(4) -0.004(4) -0.012(4) C30 0.052(5) 0.060(6) 0.058(5) -0.028(4) -0.004(4) -0.005(4) C31 0.064(6) 0.062(6) 0.059(5) -0.022(4) 0.001(4) -0.025(5) C32 0.091(7) 0.051(6) 0.069(6) -0.024(5) -0.011(5) -0.015(5) C33 0.070(6) 0.046(5) 0.060(5) -0.015(4) -0.016(4) -0.001(4) C34 0.080(7) 0.062(7) 0.083(7) -0.016(5) -0.028(6) -0.002(5) C35 0.088(8) 0.065(7) 0.109(9) -0.025(6) -0.023(7) -0.026(6) C36 0.092(7) 0.064(7) 0.094(8) -0.031(6) -0.047(6) 0.021(6) C37 0.053(5) 0.046(5) 0.063(5) -0.026(4) -0.011(4) -0.009(4) C38 0.070(6) 0.078(7) 0.070(6) -0.043(5) -0.002(5) -0.024(5) C39 0.079(6) 0.094(8) 0.060(6) -0.047(5) 0.017(5) -0.039(6) C40 0.047(5) 0.070(6) 0.045(4) -0.026(4) -0.002(4) -0.009(4) C41 0.053(5) 0.063(6) 0.046(5) -0.018(4) -0.004(4) -0.014(4) C42 0.061(6) 0.102(8) 0.056(5) -0.034(5) 0.007(4) -0.017(6) C43 0.048(5) 0.101(8) 0.064(6) -0.021(6) 0.008(4) -0.016(5) C44 0.056(5) 0.060(6) 0.067(6) -0.009(5) -0.010(5) -0.020(4) N1 0.050(4) 0.040(4) 0.056(4) -0.018(3) -0.017(3) 0.002(3) N2 0.048(4) 0.048(4) 0.048(4) -0.025(3) -0.008(3) -0.002(3) N3 0.060(4) 0.056(5) 0.053(4) -0.014(3) -0.015(3) -0.008(3) N4 0.048(4) 0.056(4) 0.056(4) -0.022(3) -0.005(3) -0.014(3) N5 0.056(4) 0.046(4) 0.047(4) -0.018(3) -0.002(3) -0.010(3) N6 0.053(4) 0.047(4) 0.057(4) -0.009(3) -0.002(3) -0.009(3) _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 N1 1.350(11) . ? C1 C2 1.365(13) . ? C1 H1 0.9300 . ? C2 C3 1.364(13) . ? C2 H2 0.9300 . ? C3 C4 1.387(11) . ? C3 H3 0.9300 . ? C4 N1 1.396(10) . ? C4 C5 1.416(10) . ? C5 C15 1.369(11) . ? C5 C6 1.524(11) . ? C6 C11 1.382(12) . ? C6 C7 1.386(11) . ? C7 C8 1.423(14) . ? C7 C12 1.499(13) . ? C8 C9 1.346(16) . ? C8 H8 0.9300 . ? C9 C10 1.387(17) . ? C9 C13 1.507(14) . ? C10 C11 1.379(13) . ? C10 H10 0.9300 . ? C11 C14 1.502(13) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 N2 1.388(10) . ? C15 C16 1.432(11) . ? C16 C17 1.352(12) . ? C16 H16 0.9300 . ? C17 C18 1.410(12) . ? C17 H17 0.9300 . ? C18 N2 1.347(10) . ? C18 C19 1.415(11) . ? C19 N3 1.363(11) . ? C19 C20 1.393(12) . ? C20 C21 1.366(13) . ? C20 H20 0.9300 . ? C21 C22 1.357(13) . ? C21 H21 0.9300 . ? C22 N3 1.353(11) . ? C22 H22 0.9300 . ? C23 N4 1.344(11) . ? C23 C24 1.387(13) . ? C23 H23 0.9300 . ? C24 C25 1.368(13) . ? C24 H24 0.9300 . ? C25 C26 1.375(11) . ? C25 H25 0.9300 . ? C26 N4 1.363(10) . ? C26 C27 1.440(11) . ? C27 C37 1.369(12) . ? C27 C28 1.508(11) . ? C28 C29 1.395(12) . ? C28 C33 1.403(12) . ? C29 C30 1.398(11) . ? C29 C34 1.509(13) . ? C30 C31 1.362(13) . ? C30 H30 0.9300 . ? C31 C32 1.363(14) . ? C31 C35 1.516(12) . ? C32 C33 1.406(12) . ? C32 H32 0.9300 . ? C33 C36 1.500(13) . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 N5 1.416(10) . ? C37 C38 1.431(12) . ? C38 C39 1.347(13) . ? C38 H38 0.9300 . ? C39 C40 1.422(12) . ? C39 H39 0.9300 . ? C40 N5 1.339(10) . ? C40 C41 1.428(11) . ? C41 N6 1.359(11) . ? C41 C42 1.375(12) . ? C42 C43 1.373(14) . ? C42 H42 0.9300 . ? C43 C44 1.337(13) . ? C43 H43 0.9300 . ? C44 N6 1.371(10) . ? C44 H44 0.9300 . ? N1 H1A 0.8600 . ? N3 H3A 0.8600 . ? N4 H4 0.8600 . ? N6 H6 0.8600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 107.1(8) . . ? N1 C1 H1 126.4 . . ? C2 C1 H1 126.4 . . ? C3 C2 C1 108.8(8) . . ? C3 C2 H2 125.6 . . ? C1 C2 H2 125.6 . . ? C2 C3 C4 108.9(8) . . ? C2 C3 H3 125.5 . . ? C4 C3 H3 125.5 . . ? C3 C4 N1 104.7(7) . . ? C3 C4 C5 129.8(7) . . ? N1 C4 C5 125.5(7) . . ? C15 C5 C4 126.9(7) . . ? C15 C5 C6 118.8(7) . . ? C4 C5 C6 114.2(6) . . ? C11 C6 C7 122.7(8) . . ? C11 C6 C5 118.6(7) . . ? C7 C6 C5 118.7(7) . . ? C6 C7 C8 116.1(9) . . ? C6 C7 C12 123.4(8) . . ? C8 C7 C12 120.5(9) . . ? C9 C8 C7 123.4(10) . . ? C9 C8 H8 118.3 . . ? C7 C8 H8 118.3 . . ? C8 C9 C10 117.1(10) . . ? C8 C9 C13 123.6(13) . . ? C10 C9 C13 119.3(13) . . ? C11 C10 C9 123.4(11) . . ? C11 C10 H10 118.3 . . ? C9 C10 H10 118.3 . . ? C10 C11 C6 117.3(9) . . ? C10 C11 C14 120.8(9) . . ? C6 C11 C14 121.8(8) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C5 C15 N2 124.7(7) . . ? C5 C15 C16 126.2(8) . . ? N2 C15 C16 109.2(7) . . ? C17 C16 C15 106.2(8) . . ? C17 C16 H16 126.9 . . ? C15 C16 H16 126.9 . . ? C16 C17 C18 108.0(8) . . ? C16 C17 H17 126.0 . . ? C18 C17 H17 126.0 . . ? N2 C18 C17 110.4(7) . . ? N2 C18 C19 123.4(7) . . ? C17 C18 C19 126.2(8) . . ? N3 C19 C20 105.6(8) . . ? N3 C19 C18 123.4(7) . . ? C20 C19 C18 131.0(9) . . ? C21 C20 C19 107.7(9) . . ? C21 C20 H20 126.1 . . ? C19 C20 H20 126.1 . . ? C22 C21 C20 109.1(9) . . ? C22 C21 H21 125.4 . . ? C20 C21 H21 125.4 . . ? N3 C22 C21 106.8(9) . . ? N3 C22 H22 126.6 . . ? C21 C22 H22 126.6 . . ? N4 C23 C24 107.1(8) . . ? N4 C23 H23 126.5 . . ? C24 C23 H23 126.5 . . ? C25 C24 C23 107.4(8) . . ? C25 C24 H24 126.3 . . ? C23 C24 H24 126.3 . . ? C24 C25 C26 108.8(8) . . ? C24 C25 H25 125.6 . . ? C26 C25 H25 125.6 . . ? N4 C26 C25 106.3(7) . . ? N4 C26 C27 125.0(7) . . ? C25 C26 C27 128.5(8) . . ? C37 C27 C26 127.8(8) . . ? C37 C27 C28 117.1(7) . . ? C26 C27 C28 115.1(7) . . ? C29 C28 C33 120.8(8) . . ? C29 C28 C27 119.8(7) . . ? C33 C28 C27 119.4(8) . . ? C28 C29 C30 117.8(8) . . ? C28 C29 C34 121.9(8) . . ? C30 C29 C34 120.3(8) . . ? C31 C30 C29 122.8(9) . . ? C31 C30 H30 118.6 . . ? C29 C30 H30 118.6 . . ? C30 C31 C32 118.7(9) . . ? C30 C31 C35 120.1(10) . . ? C32 C31 C35 121.2(9) . . ? C31 C32 C33 122.1(9) . . ? C31 C32 H32 119.0 . . ? C33 C32 H32 119.0 . . ? C28 C33 C32 117.9(9) . . ? C28 C33 C36 120.8(8) . . ? C32 C33 C36 121.4(9) . . ? C29 C34 H34A 109.5 . . ? C29 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C29 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C31 C35 H35A 109.5 . . ? C31 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? C31 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C33 C36 H36A 109.5 . . ? C33 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C33 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C27 C37 N5 123.4(7) . . ? C27 C37 C38 127.3(8) . . ? N5 C37 C38 109.2(7) . . ? C39 C38 C37 106.5(8) . . ? C39 C38 H38 126.7 . . ? C37 C38 H38 126.7 . . ? C38 C39 C40 107.7(8) . . ? C38 C39 H39 126.1 . . ? C40 C39 H39 126.1 . . ? N5 C40 C39 111.4(7) . . ? N5 C40 C41 122.0(8) . . ? C39 C40 C41 126.6(8) . . ? N6 C41 C42 105.4(8) . . ? N6 C41 C40 122.2(7) . . ? C42 C41 C40 132.4(9) . . ? C43 C42 C41 108.7(9) . . ? C43 C42 H42 125.6 . . ? C41 C42 H42 125.6 . . ? C44 C43 C42 108.6(8) . . ? C44 C43 H43 125.7 . . ? C42 C43 H43 125.7 . . ? C43 C44 N6 107.0(8) . . ? C43 C44 H44 126.5 . . ? N6 C44 H44 126.5 . . ? C1 N1 C4 110.4(7) . . ? C1 N1 H1A 124.8 . . ? C4 N1 H1A 124.8 . . ? C18 N2 C15 106.2(7) . . ? C22 N3 C19 110.8(8) . . ? C22 N3 H3A 124.6 . . ? C19 N3 H3A 124.6 . . ? C23 N4 C26 110.5(7) . . ? C23 N4 H4 124.7 . . ? C26 N4 H4 124.7 . . ? C40 N5 C37 105.1(7) . . ? C41 N6 C44 110.3(8) . . ? C41 N6 H6 124.8 . . ? C44 N6 H6 124.8 . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.599 _refine_diff_density_min -0.407 _refine_diff_density_rms 0.128 #===END