# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name H.Maeda K.Kinoshita K.Naritani _publ_contact_author_name 'Hiromitsu Maeda' _publ_contact_author_email maedahir@ph.ritsumei.ac.jp data_01214mae _database_code_depnum_ccdc_archive 'CCDC 809340' #TrackingRef '- Self2mer_HMaeda.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H42 B F2 N3 O4' _chemical_formula_weight 557.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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/a _symmetry_space_group_name_Hall '-P 2yab' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 18.0991(3) _cell_length_b 10.0405(2) _cell_length_c 18.2608(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.7402(10) _cell_angle_gamma 90.00 _cell_volume 3037.62(9) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 20204 _cell_measurement_theta_min 4.405 _cell_measurement_theta_max 68.18 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.724 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7136 _exptl_absorpt_correction_T_max 0.8688 _exptl_absorpt_process_details ; Higashi, T. (1995). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 1.54187 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 29033 _diffrn_reflns_av_R_equivalents 0.0658 _diffrn_reflns_av_sigmaI/netI 0.0678 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 4.91 _diffrn_reflns_theta_max 68.21 _reflns_number_total 5521 _reflns_number_gt 3403 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _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^)+(0.1000P)^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 5521 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1144 _refine_ls_R_factor_gt 0.0720 _refine_ls_wR_factor_ref 0.2205 _refine_ls_wR_factor_gt 0.1867 _refine_ls_goodness_of_fit_ref 1.219 _refine_ls_restrained_S_all 1.219 _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 F2 F 0.34657(6) 0.46743(13) 0.09136(7) 0.0464(4) Uani 1 1 d . . . F1 F 0.32822(6) 0.68493(13) 0.05355(7) 0.0447(4) Uani 1 1 d . . . O1 O 0.45769(7) 0.59420(15) 0.10090(8) 0.0388(4) Uani 1 1 d . . . O2 O 0.38857(7) 0.63102(15) 0.18960(8) 0.0385(4) Uani 1 1 d . . . C7 C 0.43394(11) 0.7811(2) 0.29590(13) 0.0347(6) Uani 1 1 d . . . C1 C 0.51164(11) 0.6847(2) 0.14177(12) 0.0345(6) Uani 1 1 d . . . C3 C 0.44230(11) 0.7234(2) 0.22785(13) 0.0353(6) Uani 1 1 d . . . C4 C 0.57880(11) 0.6989(2) 0.12047(13) 0.0362(6) Uani 1 1 d . . . C6 C 0.69819(11) 0.7704(2) 0.12996(13) 0.0374(6) Uani 1 1 d . . . H29 H 0.7486 0.8154 0.1483 0.045 Uiso 1 1 calc R . . C2 C 0.50272(11) 0.7568(2) 0.20295(13) 0.0366(6) Uani 1 1 d . . . H38 H 0.5381 0.8288 0.2275 0.044 Uiso 1 1 calc R . . C5 C 0.66800(11) 0.6890(2) 0.06388(13) 0.0382(6) Uani 1 1 d . . . H30 H 0.6939 0.6677 0.0293 0.046 Uiso 1 1 calc R . . C8 C 0.46032(12) 0.9213(3) 0.39798(13) 0.0455(7) Uani 1 1 d . . . H31 H 0.4841 0.9906 0.4355 0.055 Uiso 1 1 calc R . . C9 C 0.39791(12) 0.8404(2) 0.39522(14) 0.0461(7) Uani 1 1 d . . . H32 H 0.3712 0.8437 0.4306 0.055 Uiso 1 1 calc R . . B1 B 0.37878(13) 0.5942(3) 0.10666(15) 0.0348(6) Uani 1 1 d . . . O4 O 0.20776(9) 0.57701(17) 0.30225(9) 0.0508(5) Uani 1 1 d . . . O3 O 0.10081(8) 0.48430(17) 0.31322(9) 0.0505(5) Uani 1 1 d . . . C15 C 0.23133(12) 0.4116(2) 0.40087(13) 0.0405(6) Uani 1 1 d . . . C16 C 0.17527(12) 0.5002(2) 0.33259(14) 0.0423(6) Uani 1 1 d . . . C14 C 0.31466(13) 0.4169(3) 0.42568(14) 0.0484(7) Uani 1 1 d . . . H33 H 0.3379 0.4779 0.4012 0.058 Uiso 1 1 calc R . . C13 C 0.36418(14) 0.3329(3) 0.48622(15) 0.0535(7) Uani 1 1 d . . . H34 H 0.4211 0.3362 0.5028 0.064 Uiso 1 1 calc R . . C10 C 0.19909(13) 0.3229(2) 0.43850(14) 0.0473(7) Uani 1 1 d . . . H35 H 0.1423 0.3199 0.4228 0.057 Uiso 1 1 calc R . . C11 C 0.24791(14) 0.2395(3) 0.49806(15) 0.0541(7) Uani 1 1 d . . . H36 H 0.2249 0.1783 0.5226 0.065 Uiso 1 1 calc R . . C12 C 0.33054(14) 0.2454(3) 0.52185(16) 0.0576(8) Uani 1 1 d . . . H37 H 0.3644 0.1883 0.5632 0.069 Uiso 1 1 calc R . . N1 N 0.27555(10) 0.17248(18) 0.20542(11) 0.0402(5) Uani 1 1 d . . . C17 C 0.35398(13) 0.2112(3) 0.27307(15) 0.0484(7) Uani 1 1 d . . . H15 H 0.3893 0.1317 0.2886 0.058 Uiso 1 1 calc R . . H16 H 0.3422 0.2364 0.3197 0.058 Uiso 1 1 calc R . . C20 C 0.28944(12) 0.1325(2) 0.13103(14) 0.0453(6) Uani 1 1 d . . . H8 H 0.2377 0.0989 0.0904 0.054 Uiso 1 1 calc R . . H9 H 0.3036 0.2138 0.1088 0.054 Uiso 1 1 calc R . . C21 C 0.35360(12) 0.0289(3) 0.14208(14) 0.0502(7) Uani 1 1 d . . . H10 H 0.3387 -0.0559 0.1603 0.060 Uiso 1 1 calc R . . H11 H 0.4058 0.0591 0.1834 0.060 Uiso 1 1 calc R . . C18 C 0.40065(14) 0.3237(3) 0.25668(17) 0.0596(8) Uani 1 1 d . . . H17 H 0.3687 0.4069 0.2466 0.071 Uiso 1 1 calc R . . H18 H 0.4106 0.3031 0.2084 0.071 Uiso 1 1 calc R . . C22 C 0.36179(12) 0.0072(3) 0.06326(14) 0.0478(7) Uani 1 1 d . . . H12 H 0.3100 -0.0226 0.0226 0.072 Uiso 1 1 calc R . . H13 H 0.4030 -0.0607 0.0704 0.072 Uiso 1 1 calc R . . H14 H 0.3777 0.0909 0.0461 0.072 Uiso 1 1 calc R . . C19 C 0.48126(15) 0.3429(3) 0.32846(19) 0.0773(11) Uani 1 1 d . . . H19 H 0.4713 0.3596 0.3766 0.116 Uiso 1 1 calc R . . H20 H 0.5099 0.4191 0.3186 0.116 Uiso 1 1 calc R . . H21 H 0.5142 0.2625 0.3361 0.116 Uiso 1 1 calc R . . N3 N 0.64537(9) 0.77643(18) 0.16462(11) 0.0364(5) Uani 1 1 d . . . H41 H 0.6519 0.8219 0.2080 0.044 Uiso 1 1 calc R . . N2 N 0.48221(9) 0.88518(19) 0.33802(11) 0.0399(5) Uani 1 1 d . . . H42 H 0.5210 0.9222 0.3276 0.048 Uiso 1 1 calc R . . C23 C 0.59273(11) 0.6432(2) 0.05674(13) 0.0360(6) Uani 1 1 d . . . H39 H 0.5577 0.5855 0.0165 0.043 Uiso 1 1 calc R . . C24 C 0.38080(11) 0.7525(2) 0.33117(13) 0.0414(6) Uani 1 1 d . . . H40 H 0.3403 0.6856 0.3148 0.050 Uiso 1 1 calc R . . C25 C 0.21721(12) 0.2885(2) 0.18218(15) 0.0456(7) Uani 1 1 d . . . H1 H 0.2151 0.3255 0.2316 0.055 Uiso 1 1 calc R . . H2 H 0.2394 0.3588 0.1587 0.055 Uiso 1 1 calc R . . C26 C 0.13185(13) 0.2591(2) 0.12388(16) 0.0522(7) Uani 1 1 d . . . H3 H 0.1082 0.1898 0.1465 0.063 Uiso 1 1 calc R . . H4 H 0.1324 0.2246 0.0733 0.063 Uiso 1 1 calc R . . C27 C 0.24080(13) 0.0538(2) 0.23320(14) 0.0463(7) Uani 1 1 d . . . H22 H 0.1921 0.0222 0.1876 0.056 Uiso 1 1 calc R . . H23 H 0.2809 -0.0193 0.2483 0.056 Uiso 1 1 calc R . . C28 C 0.21842(14) 0.0817(3) 0.30286(15) 0.0537(7) Uani 1 1 d . . . H24 H 0.1816 0.1593 0.2901 0.064 Uiso 1 1 calc R . . H25 H 0.2677 0.1042 0.3505 0.064 Uiso 1 1 calc R . . C29 C 0.17769(13) -0.0372(2) 0.32149(14) 0.0500(7) Uani 1 1 d . . . H26 H 0.1265 -0.0549 0.2760 0.075 Uiso 1 1 calc R . . H27 H 0.1673 -0.0185 0.3692 0.075 Uiso 1 1 calc R . . H28 H 0.2129 -0.1153 0.3313 0.075 Uiso 1 1 calc R . . C30 C 0.08032(13) 0.3849(3) 0.10690(15) 0.0551(8) Uani 1 1 d . . . H5 H 0.0757 0.4142 0.1561 0.083 Uiso 1 1 calc R . . H6 H 0.0264 0.3659 0.0658 0.083 Uiso 1 1 calc R . . H7 H 0.1057 0.4553 0.0879 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 F2 0.0446(6) 0.0418(7) 0.0603(7) -0.0085(6) 0.0289(5) -0.0112(6) F1 0.0342(5) 0.0504(8) 0.0515(7) -0.0008(6) 0.0194(5) 0.0011(6) O1 0.0304(6) 0.0386(9) 0.0523(8) -0.0078(7) 0.0217(6) -0.0051(6) O2 0.0324(6) 0.0399(9) 0.0487(8) -0.0036(7) 0.0219(6) -0.0059(6) C7 0.0299(8) 0.0352(12) 0.0424(11) -0.0025(10) 0.0179(8) -0.0001(9) C1 0.0316(9) 0.0283(11) 0.0460(11) 0.0008(10) 0.0181(8) 0.0016(9) C3 0.0264(8) 0.0312(12) 0.0493(12) 0.0029(10) 0.0163(8) 0.0050(9) C4 0.0295(8) 0.0323(12) 0.0517(12) 0.0022(10) 0.0213(8) 0.0026(9) C6 0.0310(9) 0.0380(13) 0.0501(12) 0.0012(10) 0.0236(8) -0.0018(9) C2 0.0282(9) 0.0354(12) 0.0488(12) -0.0021(10) 0.0183(8) -0.0011(9) C5 0.0367(9) 0.0397(13) 0.0481(11) 0.0019(10) 0.0272(8) 0.0025(9) C8 0.0404(10) 0.0558(15) 0.0435(12) -0.0055(11) 0.0204(9) 0.0044(11) C9 0.0451(10) 0.0566(16) 0.0458(12) -0.0011(11) 0.0277(9) 0.0055(11) B1 0.0257(9) 0.0382(14) 0.0440(13) -0.0043(11) 0.0175(9) -0.0048(10) O4 0.0458(8) 0.0509(10) 0.0551(9) 0.0081(8) 0.0198(7) -0.0003(8) O3 0.0380(7) 0.0523(10) 0.0619(10) 0.0040(8) 0.0210(7) 0.0070(7) C15 0.0396(10) 0.0388(13) 0.0459(12) -0.0013(10) 0.0201(9) 0.0073(10) C16 0.0413(10) 0.0332(12) 0.0568(13) -0.0059(11) 0.0245(9) 0.0010(10) C14 0.0415(10) 0.0494(15) 0.0579(13) 0.0004(12) 0.0238(10) 0.0033(11) C13 0.0388(11) 0.0578(16) 0.0599(15) 0.0046(13) 0.0157(11) 0.0120(11) C10 0.0420(10) 0.0495(15) 0.0553(13) -0.0036(12) 0.0246(10) 0.0022(11) C11 0.0581(12) 0.0510(16) 0.0591(14) 0.0120(12) 0.0299(11) 0.0115(12) C12 0.0552(13) 0.0614(18) 0.0568(15) 0.0130(13) 0.0232(11) 0.0210(13) N1 0.0380(8) 0.0342(11) 0.0499(10) 0.0003(9) 0.0191(8) -0.0021(8) C17 0.0414(11) 0.0473(15) 0.0522(14) 0.0017(12) 0.0144(10) -0.0013(11) C20 0.0401(10) 0.0465(14) 0.0536(13) 0.0013(11) 0.0234(9) 0.0032(10) C21 0.0394(10) 0.0522(15) 0.0641(14) 0.0080(12) 0.0260(10) 0.0031(11) C18 0.0505(13) 0.0534(17) 0.0722(17) 0.0023(14) 0.0220(12) -0.0083(12) C22 0.0379(10) 0.0487(15) 0.0638(14) 0.0048(12) 0.0278(10) 0.0031(11) C19 0.0424(13) 0.092(2) 0.083(2) 0.0105(18) 0.0102(14) -0.0144(15) N3 0.0312(7) 0.0355(10) 0.0476(9) -0.0042(8) 0.0211(7) -0.0034(7) N2 0.0317(8) 0.0457(11) 0.0458(10) -0.0001(9) 0.0194(7) 0.0007(8) C23 0.0329(9) 0.0340(12) 0.0443(11) -0.0021(10) 0.0187(8) 0.0010(9) C24 0.0321(9) 0.0457(14) 0.0490(12) 0.0041(11) 0.0192(9) 0.0018(10) C25 0.0410(10) 0.0382(13) 0.0604(14) 0.0026(11) 0.0231(10) 0.0044(10) C26 0.0440(11) 0.0483(15) 0.0645(15) -0.0049(13) 0.0220(11) 0.0063(11) C27 0.0467(11) 0.0387(14) 0.0562(13) 0.0038(11) 0.0234(10) -0.0003(10) C28 0.0546(12) 0.0553(16) 0.0579(14) -0.0044(13) 0.0297(11) -0.0023(12) C29 0.0503(11) 0.0484(15) 0.0589(14) -0.0035(12) 0.0299(10) -0.0080(11) C30 0.0431(11) 0.0593(17) 0.0625(15) -0.0019(13) 0.0209(11) 0.0111(12) _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 F2 B1 1.381(3) . ? F1 B1 1.376(3) . ? O1 C1 1.323(2) . ? O1 B1 1.474(3) . ? O2 C3 1.321(2) . ? O2 B1 1.499(3) . ? C7 N2 1.381(3) . ? C7 C24 1.386(3) . ? C7 C3 1.433(3) . ? C1 C2 1.394(3) . ? C1 C4 1.425(3) . ? C3 C2 1.384(3) . ? C4 N3 1.388(2) . ? C4 C23 1.402(3) . ? C6 N3 1.344(3) . ? C6 C5 1.376(3) . ? C6 H29 0.9500 . ? C2 H38 0.9500 . ? C5 C23 1.393(3) . ? C5 H30 0.9500 . ? C8 N2 1.355(3) . ? C8 C9 1.375(3) . ? C8 H31 0.9500 . ? C9 C24 1.397(3) . ? C9 H32 0.9500 . ? O4 C16 1.228(3) . ? O3 C16 1.258(2) . ? C15 C10 1.388(3) . ? C15 C14 1.390(3) . ? C15 C16 1.536(3) . ? C14 C13 1.392(3) . ? C14 H33 0.9500 . ? C13 C12 1.373(4) . ? C13 H34 0.9500 . ? C10 C11 1.375(3) . ? C10 H35 0.9500 . ? C11 C12 1.381(3) . ? C11 H36 0.9500 . ? C12 H37 0.9500 . ? N1 C17 1.510(3) . ? N1 C25 1.514(3) . ? N1 C27 1.526(3) . ? N1 C20 1.531(3) . ? C17 C18 1.511(4) . ? C17 H15 0.9900 . ? C17 H16 0.9900 . ? C20 C21 1.511(3) . ? C20 H8 0.9900 . ? C20 H9 0.9900 . ? C21 C22 1.521(3) . ? C21 H10 0.9900 . ? C21 H11 0.9900 . ? C18 C19 1.531(3) . ? C18 H17 0.9900 . ? C18 H18 0.9900 . ? C22 H12 0.9800 . ? C22 H13 0.9800 . ? C22 H14 0.9800 . ? C19 H19 0.9800 . ? C19 H20 0.9800 . ? C19 H21 0.9800 . ? N3 H41 0.8800 . ? N2 H42 0.8800 . ? C23 H39 0.9500 . ? C24 H40 0.9500 . ? C25 C26 1.511(3) . ? C25 H1 0.9900 . ? C25 H2 0.9900 . ? C26 C30 1.525(3) . ? C26 H3 0.9900 . ? C26 H4 0.9900 . ? C27 C28 1.508(4) . ? C27 H22 0.9900 . ? C27 H23 0.9900 . ? C28 C29 1.512(4) . ? C28 H24 0.9900 . ? C28 H25 0.9900 . ? C29 H26 0.9800 . ? C29 H27 0.9800 . ? C29 H28 0.9800 . ? C30 H5 0.9800 . ? C30 H6 0.9800 . ? C30 H7 0.9800 . ? 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 C1 O1 B1 118.44(17) . . ? C3 O2 B1 118.02(17) . . ? N2 C7 C24 107.4(2) . . ? N2 C7 C3 121.68(19) . . ? C24 C7 C3 130.9(2) . . ? O1 C1 C2 120.77(19) . . ? O1 C1 C4 115.58(19) . . ? C2 C1 C4 123.62(18) . . ? O2 C3 C2 120.5(2) . . ? O2 C3 C7 115.47(19) . . ? C2 C3 C7 124.03(19) . . ? N3 C4 C23 107.55(18) . . ? N3 C4 C1 122.3(2) . . ? C23 C4 C1 130.16(19) . . ? N3 C6 C5 109.47(18) . . ? N3 C6 H29 125.3 . . ? C5 C6 H29 125.3 . . ? C3 C2 C1 119.93(19) . . ? C3 C2 H38 120.0 . . ? C1 C2 H38 120.0 . . ? C6 C5 C23 107.8(2) . . ? C6 C5 H30 126.1 . . ? C23 C5 H30 126.1 . . ? N2 C8 C9 108.4(2) . . ? N2 C8 H31 125.8 . . ? C9 C8 H31 125.8 . . ? C8 C9 C24 107.8(2) . . ? C8 C9 H32 126.1 . . ? C24 C9 H32 126.1 . . ? F1 B1 F2 111.16(16) . . ? F1 B1 O1 109.77(19) . . ? F2 B1 O1 109.15(19) . . ? F1 B1 O2 108.87(19) . . ? F2 B1 O2 107.48(19) . . ? O1 B1 O2 110.38(15) . . ? C10 C15 C14 118.7(2) . . ? C10 C15 C16 120.10(19) . . ? C14 C15 C16 121.2(2) . . ? O4 C16 O3 127.3(2) . . ? O4 C16 C15 116.76(18) . . ? O3 C16 C15 115.9(2) . . ? C15 C14 C13 120.2(2) . . ? C15 C14 H33 119.9 . . ? C13 C14 H33 119.9 . . ? C12 C13 C14 119.8(2) . . ? C12 C13 H34 120.1 . . ? C14 C13 H34 120.1 . . ? C11 C10 C15 121.2(2) . . ? C11 C10 H35 119.4 . . ? C15 C10 H35 119.4 . . ? C10 C11 C12 119.5(3) . . ? C10 C11 H36 120.2 . . ? C12 C11 H36 120.2 . . ? C13 C12 C11 120.6(2) . . ? C13 C12 H37 119.7 . . ? C11 C12 H37 119.7 . . ? C17 N1 C25 110.54(17) . . ? C17 N1 C27 107.85(17) . . ? C25 N1 C27 111.08(17) . . ? C17 N1 C20 110.94(17) . . ? C25 N1 C20 107.35(17) . . ? C27 N1 C20 109.09(17) . . ? N1 C17 C18 116.5(2) . . ? N1 C17 H15 108.2 . . ? C18 C17 H15 108.2 . . ? N1 C17 H16 108.2 . . ? C18 C17 H16 108.2 . . ? H15 C17 H16 107.3 . . ? C21 C20 N1 116.99(18) . . ? C21 C20 H8 108.0 . . ? N1 C20 H8 108.0 . . ? C21 C20 H9 108.0 . . ? N1 C20 H9 108.0 . . ? H8 C20 H9 107.3 . . ? C20 C21 C22 109.56(19) . . ? C20 C21 H10 109.8 . . ? C22 C21 H10 109.8 . . ? C20 C21 H11 109.8 . . ? C22 C21 H11 109.8 . . ? H10 C21 H11 108.2 . . ? C17 C18 C19 109.9(2) . . ? C17 C18 H17 109.7 . . ? C19 C18 H17 109.7 . . ? C17 C18 H18 109.7 . . ? C19 C18 H18 109.7 . . ? H17 C18 H18 108.2 . . ? C21 C22 H12 109.5 . . ? C21 C22 H13 109.5 . . ? H12 C22 H13 109.5 . . ? C21 C22 H14 109.5 . . ? H12 C22 H14 109.5 . . ? H13 C22 H14 109.5 . . ? C18 C19 H19 109.5 . . ? C18 C19 H20 109.5 . . ? H19 C19 H20 109.5 . . ? C18 C19 H21 109.5 . . ? H19 C19 H21 109.5 . . ? H20 C19 H21 109.5 . . ? C6 N3 C4 108.49(18) . . ? C6 N3 H41 125.8 . . ? C4 N3 H41 125.8 . . ? C8 N2 C7 109.11(19) . . ? C8 N2 H42 125.4 . . ? C7 N2 H42 125.4 . . ? C5 C23 C4 106.67(18) . . ? C5 C23 H39 126.7 . . ? C4 C23 H39 126.7 . . ? C7 C24 C9 107.3(2) . . ? C7 C24 H40 126.4 . . ? C9 C24 H40 126.4 . . ? C26 C25 N1 116.56(19) . . ? C26 C25 H1 108.2 . . ? N1 C25 H1 108.2 . . ? C26 C25 H2 108.2 . . ? N1 C25 H2 108.2 . . ? H1 C25 H2 107.3 . . ? C25 C26 C30 110.5(2) . . ? C25 C26 H3 109.6 . . ? C30 C26 H3 109.6 . . ? C25 C26 H4 109.6 . . ? C30 C26 H4 109.6 . . ? H3 C26 H4 108.1 . . ? C28 C27 N1 115.0(2) . . ? C28 C27 H22 108.5 . . ? N1 C27 H22 108.5 . . ? C28 C27 H23 108.5 . . ? N1 C27 H23 108.5 . . ? H22 C27 H23 107.5 . . ? C27 C28 C29 111.4(2) . . ? C27 C28 H24 109.4 . . ? C29 C28 H24 109.4 . . ? C27 C28 H25 109.4 . . ? C29 C28 H25 109.4 . . ? H24 C28 H25 108.0 . . ? C28 C29 H26 109.5 . . ? C28 C29 H27 109.5 . . ? H26 C29 H27 109.5 . . ? C28 C29 H28 109.5 . . ? H26 C29 H28 109.5 . . ? H27 C29 H28 109.5 . . ? C26 C30 H5 109.5 . . ? C26 C30 H6 109.5 . . ? H5 C30 H6 109.5 . . ? C26 C30 H7 109.5 . . ? H5 C30 H7 109.5 . . ? H6 C30 H7 109.5 . . ? 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 B1 O1 C1 C2 15.2(3) . . . . ? B1 O1 C1 C4 -166.66(18) . . . . ? B1 O2 C3 C2 -18.2(3) . . . . ? B1 O2 C3 C7 163.23(18) . . . . ? N2 C7 C3 O2 -175.32(17) . . . . ? C24 C7 C3 O2 3.3(3) . . . . ? N2 C7 C3 C2 6.2(3) . . . . ? C24 C7 C3 C2 -175.2(2) . . . . ? O1 C1 C4 N3 -171.26(18) . . . . ? C2 C1 C4 N3 6.8(3) . . . . ? O1 C1 C4 C23 8.3(3) . . . . ? C2 C1 C4 C23 -173.6(2) . . . . ? O2 C3 C2 C1 -5.8(3) . . . . ? C7 C3 C2 C1 172.63(19) . . . . ? O1 C1 C2 C3 7.6(3) . . . . ? C4 C1 C2 C3 -170.3(2) . . . . ? N3 C6 C5 C23 0.5(2) . . . . ? N2 C8 C9 C24 -0.3(3) . . . . ? C1 O1 B1 F1 83.9(2) . . . . ? C1 O1 B1 F2 -154.05(17) . . . . ? C1 O1 B1 O2 -36.1(3) . . . . ? C3 O2 B1 F1 -82.8(2) . . . . ? C3 O2 B1 F2 156.71(16) . . . . ? C3 O2 B1 O1 37.8(2) . . . . ? C10 C15 C16 O4 179.5(2) . . . . ? C14 C15 C16 O4 -1.2(3) . . . . ? C10 C15 C16 O3 -1.5(3) . . . . ? C14 C15 C16 O3 177.8(2) . . . . ? C10 C15 C14 C13 1.1(4) . . . . ? C16 C15 C14 C13 -178.2(2) . . . . ? C15 C14 C13 C12 -0.5(4) . . . . ? C14 C15 C10 C11 -1.4(4) . . . . ? C16 C15 C10 C11 177.9(2) . . . . ? C15 C10 C11 C12 1.1(4) . . . . ? C14 C13 C12 C11 0.1(4) . . . . ? C10 C11 C12 C13 -0.5(4) . . . . ? C25 N1 C17 C18 -61.1(3) . . . . ? C27 N1 C17 C18 177.3(2) . . . . ? C20 N1 C17 C18 57.9(3) . . . . ? C17 N1 C20 C21 52.0(3) . . . . ? C25 N1 C20 C21 172.82(19) . . . . ? C27 N1 C20 C21 -66.7(2) . . . . ? N1 C20 C21 C22 -177.14(18) . . . . ? N1 C17 C18 C19 -175.5(2) . . . . ? C5 C6 N3 C4 -0.6(2) . . . . ? C23 C4 N3 C6 0.4(2) . . . . ? C1 C4 N3 C6 -179.91(19) . . . . ? C9 C8 N2 C7 0.2(2) . . . . ? C24 C7 N2 C8 0.0(2) . . . . ? C3 C7 N2 C8 178.90(19) . . . . ? C6 C5 C23 C4 -0.3(2) . . . . ? N3 C4 C23 C5 -0.1(2) . . . . ? C1 C4 C23 C5 -179.7(2) . . . . ? N2 C7 C24 C9 -0.2(2) . . . . ? C3 C7 C24 C9 -179.0(2) . . . . ? C8 C9 C24 C7 0.3(2) . . . . ? C17 N1 C25 C26 -171.1(2) . . . . ? C27 N1 C25 C26 -51.4(3) . . . . ? C20 N1 C25 C26 67.8(3) . . . . ? N1 C25 C26 C30 179.5(2) . . . . ? C17 N1 C27 C28 63.6(2) . . . . ? C25 N1 C27 C28 -57.7(2) . . . . ? C20 N1 C27 C28 -175.85(17) . . . . ? N1 C27 C28 C29 174.85(17) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 68.21 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.252 _refine_diff_density_min -0.291 _refine_diff_density_rms 0.056