# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Lei Zhu' _publ_contact_author_email LZHU@CHEM.FSU.EDU loop_ _publ_author_name L.Zhu R.J.Clark J.A.Kerszulis T.Ye L.Zhang data_zhu24 _database_code_depnum_ccdc_archive 'CCDC 715264' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H28 B N O3' _chemical_formula_sum 'C30 H28 B N O3' _chemical_formula_weight 461.34 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' 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 P2(1)/n _symmetry_space_group_name_Hall -p2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 15.4162(4) _cell_length_b 7.3575(2) _cell_length_c 20.8718(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.8650(10) _cell_angle_gamma 90.00 _cell_volume 2364.42(11) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 9969 _cell_measurement_theta_min 2.65 _cell_measurement_theta_max 28.22 _exptl_crystal_description rectangular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.296 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 0.984 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 30530 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0155 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 26.37 _reflns_number_total 4833 _reflns_number_gt 4106 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^2^+0.4139P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4833 _refine_ls_number_parameters 322 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0341 _refine_ls_wR_factor_ref 0.1229 _refine_ls_wR_factor_gt 0.1129 _refine_ls_goodness_of_fit_ref 0.883 _refine_ls_restrained_S_all 0.883 _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 0.57483(7) 1.31403(17) 0.32934(5) 0.0284(3) Uani 1 1 d . . . C2 C 0.52948(8) 1.48204(17) 0.31861(6) 0.0316(3) Uani 1 1 d . . . H2 H 0.5038 1.5074 0.2773 0.038 Uiso 1 1 calc R . . C3 C 0.52243(9) 1.60610(19) 0.36650(6) 0.0374(3) Uani 1 1 d . . . H3 H 0.4919 1.7164 0.3580 0.045 Uiso 1 1 calc R . . C4 C 0.55987(9) 1.5733(2) 0.42882(6) 0.0410(3) Uani 1 1 d . . . H4 H 0.5538 1.6604 0.4619 0.049 Uiso 1 1 calc R . . C5 C 0.60422(9) 1.4178(2) 0.44115(6) 0.0387(3) Uani 1 1 d . . . H5 H 0.6298 1.3978 0.4829 0.046 Uiso 1 1 calc R . . C6 C 0.61354(8) 1.28237(18) 0.39266(6) 0.0320(3) Uani 1 1 d . . . C7 C 0.65919(8) 1.12258(19) 0.40537(6) 0.0350(3) Uani 1 1 d . . . H7 H 0.6847 1.1031 0.4472 0.042 Uiso 1 1 calc R . . C8 C 0.66874(8) 0.99009(18) 0.35865(6) 0.0320(3) Uani 1 1 d . . . C9 C 0.71693(8) 0.8275(2) 0.37231(7) 0.0388(3) Uani 1 1 d . . . H9 H 0.7427 0.8091 0.4141 0.047 Uiso 1 1 calc R . . C10 C 0.72638(8) 0.6992(2) 0.32660(7) 0.0415(3) Uani 1 1 d . . . H10 H 0.7586 0.5919 0.3365 0.050 Uiso 1 1 calc R . . C11 C 0.68827(8) 0.72499(18) 0.26399(7) 0.0377(3) Uani 1 1 d . . . H11 H 0.6955 0.6347 0.2322 0.045 Uiso 1 1 calc R . . C12 C 0.64146(8) 0.87730(17) 0.24887(6) 0.0323(3) Uani 1 1 d . . . H12 H 0.6160 0.8909 0.2067 0.039 Uiso 1 1 calc R . . C13 C 0.62980(7) 1.01772(16) 0.29539(6) 0.0283(3) Uani 1 1 d . . . C14 C 0.58415(7) 1.18079(16) 0.28154(5) 0.0269(2) Uani 1 1 d . . . C15 C 0.55122(7) 1.21564(16) 0.21346(5) 0.0272(3) Uani 1 1 d . . . H15A H 0.5446 1.3484 0.2072 0.033 Uiso 1 1 calc R . . H15B H 0.5953 1.1727 0.1841 0.033 Uiso 1 1 calc R . . C16 C 0.39140(8) 1.20859(17) 0.22704(6) 0.0314(3) Uani 1 1 d . . . H16A H 0.4030 1.2075 0.2736 0.047 Uiso 1 1 calc R . . H16B H 0.3385 1.1390 0.2162 0.047 Uiso 1 1 calc R . . H16C H 0.3836 1.3343 0.2123 0.047 Uiso 1 1 calc R . . C17 C 0.45180(8) 1.12712(15) 0.12249(5) 0.0276(3) Uani 1 1 d . . . H17A H 0.3896 1.1068 0.1107 0.033 Uiso 1 1 calc R . . H17B H 0.4685 1.2472 0.1056 0.033 Uiso 1 1 calc R . . C18 C 0.50544(7) 0.98081(15) 0.09315(5) 0.0258(2) Uani 1 1 d . . . C19 C 0.58008(8) 1.02822(17) 0.06179(5) 0.0309(3) Uani 1 1 d . . . H19 H 0.5965 1.1523 0.0590 0.037 Uiso 1 1 calc R . . C20 C 0.63029(8) 0.8951(2) 0.03465(6) 0.0363(3) Uani 1 1 d . . . H20 H 0.6815 0.9275 0.0139 0.044 Uiso 1 1 calc R . . C21 C 0.60533(8) 0.71541(19) 0.03802(6) 0.0369(3) Uani 1 1 d . . . H21 H 0.6393 0.6236 0.0194 0.044 Uiso 1 1 calc R . . C22 C 0.53034(8) 0.66847(17) 0.06868(6) 0.0315(3) Uani 1 1 d . . . H22 H 0.5137 0.5443 0.0700 0.038 Uiso 1 1 calc R . . C23 C 0.47887(7) 0.79814(15) 0.09748(5) 0.0254(2) Uani 1 1 d . . . C24 C 0.34548(9) 0.74151(18) 0.24611(6) 0.0373(3) Uani 1 1 d . . . H24A H 0.2937 0.8080 0.2303 0.056 Uiso 1 1 calc R . . H24B H 0.3632 0.7845 0.2892 0.056 Uiso 1 1 calc R . . H24C H 0.3324 0.6113 0.2477 0.056 Uiso 1 1 calc R . . C25 C 0.28179(8) 0.54414(17) 0.10514(5) 0.0288(3) Uani 1 1 d . . . C26 C 0.22877(9) 0.39536(19) 0.09314(6) 0.0356(3) Uani 1 1 d . . . H26 H 0.2511 0.2750 0.0954 0.043 Uiso 1 1 calc R . . C27 C 0.14085(9) 0.4290(2) 0.07750(6) 0.0418(3) Uani 1 1 d . . . H27 H 0.1028 0.3293 0.0689 0.050 Uiso 1 1 calc R . . C28 C 0.10821(9) 0.6031(2) 0.07435(6) 0.0442(4) Uani 1 1 d . . . H28 H 0.0481 0.6214 0.0641 0.053 Uiso 1 1 calc R . . C29 C 0.16235(8) 0.7539(2) 0.08599(6) 0.0393(3) Uani 1 1 d . . . H29 H 0.1400 0.8741 0.0838 0.047 Uiso 1 1 calc R . . C30 C 0.24925(8) 0.72170(17) 0.10075(5) 0.0301(3) Uani 1 1 d . . . B1 B 0.39374(8) 0.73930(17) 0.13516(6) 0.0264(3) Uani 1 1 d . . . N1 N 0.46596(6) 1.12515(13) 0.19519(4) 0.0246(2) Uani 1 1 d . . . H1N H 0.4648(10) 1.002(2) 0.2078(7) 0.038(4) Uiso 1 1 d . . . O1 O 0.41418(5) 0.77163(11) 0.20413(4) 0.0298(2) Uani 1 1 d . . . O2 O 0.31261(5) 0.84474(11) 0.11399(4) 0.0320(2) Uani 1 1 d . . . O3 O 0.36790(5) 0.54487(11) 0.12261(4) 0.0300(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0247(5) 0.0351(6) 0.0256(6) -0.0021(5) 0.0030(4) -0.0050(5) C2 0.0301(6) 0.0342(6) 0.0305(6) -0.0033(5) 0.0016(5) -0.0028(5) C3 0.0347(6) 0.0377(7) 0.0403(7) -0.0073(5) 0.0060(5) -0.0022(5) C4 0.0440(7) 0.0468(8) 0.0330(7) -0.0135(6) 0.0094(6) -0.0080(6) C5 0.0406(7) 0.0504(8) 0.0253(6) -0.0064(5) 0.0034(5) -0.0089(6) C6 0.0282(6) 0.0421(7) 0.0259(6) -0.0013(5) 0.0029(5) -0.0062(5) C7 0.0297(6) 0.0494(8) 0.0256(6) 0.0042(5) -0.0014(5) -0.0052(5) C8 0.0232(5) 0.0406(7) 0.0323(6) 0.0046(5) 0.0013(5) -0.0026(5) C9 0.0267(6) 0.0483(8) 0.0413(7) 0.0105(6) -0.0005(5) 0.0017(5) C10 0.0267(6) 0.0421(7) 0.0562(9) 0.0089(6) 0.0051(6) 0.0062(5) C11 0.0291(6) 0.0378(7) 0.0468(7) -0.0027(6) 0.0080(5) 0.0014(5) C12 0.0266(6) 0.0359(6) 0.0347(6) -0.0008(5) 0.0044(5) -0.0009(5) C13 0.0220(5) 0.0339(6) 0.0292(6) 0.0016(5) 0.0042(4) -0.0027(4) C14 0.0229(5) 0.0325(6) 0.0253(5) -0.0006(4) 0.0021(4) -0.0037(4) C15 0.0268(6) 0.0294(6) 0.0255(5) -0.0023(4) 0.0019(4) -0.0026(4) C16 0.0278(6) 0.0335(6) 0.0331(6) -0.0056(5) 0.0035(5) 0.0043(5) C17 0.0326(6) 0.0265(6) 0.0233(5) -0.0004(4) -0.0028(5) 0.0015(4) C18 0.0284(6) 0.0296(6) 0.0191(5) -0.0002(4) -0.0024(4) 0.0004(4) C19 0.0323(6) 0.0361(6) 0.0242(5) 0.0007(5) -0.0016(5) -0.0059(5) C20 0.0291(6) 0.0519(8) 0.0281(6) -0.0008(5) 0.0039(5) -0.0036(5) C21 0.0327(6) 0.0445(7) 0.0339(6) -0.0050(5) 0.0064(5) 0.0086(6) C22 0.0332(6) 0.0302(6) 0.0313(6) -0.0015(5) 0.0032(5) 0.0028(5) C23 0.0257(5) 0.0285(6) 0.0219(5) -0.0010(4) -0.0008(4) 0.0019(4) C24 0.0387(7) 0.0407(7) 0.0335(6) 0.0029(5) 0.0130(5) 0.0018(6) C25 0.0270(6) 0.0359(6) 0.0239(5) 0.0007(5) 0.0041(4) -0.0011(5) C26 0.0378(7) 0.0406(7) 0.0290(6) -0.0019(5) 0.0066(5) -0.0089(5) C27 0.0351(7) 0.0607(9) 0.0300(6) -0.0025(6) 0.0051(5) -0.0165(6) C28 0.0262(6) 0.0726(10) 0.0339(7) 0.0035(6) 0.0012(5) -0.0044(6) C29 0.0313(6) 0.0533(8) 0.0333(6) 0.0069(6) 0.0018(5) 0.0068(6) C30 0.0279(6) 0.0372(6) 0.0253(6) 0.0033(5) 0.0033(4) 0.0000(5) B1 0.0266(6) 0.0235(6) 0.0291(6) 0.0001(5) 0.0026(5) 0.0023(5) N1 0.0258(5) 0.0241(5) 0.0239(5) -0.0014(4) 0.0011(4) 0.0008(4) O1 0.0301(4) 0.0334(4) 0.0265(4) 0.0004(3) 0.0060(3) 0.0000(3) O2 0.0272(4) 0.0295(4) 0.0392(5) 0.0027(3) 0.0008(3) 0.0032(3) O3 0.0264(4) 0.0256(4) 0.0380(5) -0.0005(3) 0.0015(3) 0.0003(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 C14 1.4112(16) . ? C1 C2 1.4323(17) . ? C1 C6 1.4415(16) . ? C2 C3 1.3620(17) . ? C2 H2 0.9500 . ? C3 C4 1.4171(19) . ? C3 H3 0.9500 . ? C4 C5 1.351(2) . ? C4 H4 0.9500 . ? C5 C6 1.4324(18) . ? C5 H5 0.9500 . ? C6 C7 1.3889(19) . ? C7 C8 1.3917(19) . ? C7 H7 0.9500 . ? C8 C9 1.4294(18) . ? C8 C13 1.4374(17) . ? C9 C10 1.355(2) . ? C9 H9 0.9500 . ? C10 C11 1.419(2) . ? C10 H10 0.9500 . ? C11 C12 1.3614(18) . ? C11 H11 0.9500 . ? C12 C13 1.4352(17) . ? C12 H12 0.9500 . ? C13 C14 1.4136(17) . ? C14 C15 1.5067(16) . ? C15 N1 1.5053(14) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N1 1.4888(14) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.5061(16) . ? C17 N1 1.5223(14) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.3962(16) . ? C18 C23 1.4092(16) . ? C19 C20 1.3866(18) . ? C19 H19 0.9500 . ? C20 C21 1.380(2) . ? C20 H20 0.9500 . ? C21 C22 1.3926(18) . ? C21 H21 0.9500 . ? C22 C23 1.3960(16) . ? C22 H22 0.9500 . ? C23 B1 1.6222(17) . ? C24 O1 1.4252(14) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 O3 1.3589(14) . ? C25 C26 1.3815(18) . ? C25 C30 1.4008(17) . ? C26 C27 1.4003(19) . ? C26 H26 0.9500 . ? C27 C28 1.377(2) . ? C27 H27 0.9500 . ? C28 C29 1.402(2) . ? C28 H28 0.9500 . ? C29 C30 1.3800(17) . ? C29 H29 0.9500 . ? C30 O2 1.3502(15) . ? B1 O1 1.4775(15) . ? B1 O3 1.5044(15) . ? B1 O2 1.5185(15) . ? N1 H1N 0.942(16) . ? 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 C14 C1 C2 123.71(11) . . ? C14 C1 C6 118.94(11) . . ? C2 C1 C6 117.35(11) . . ? C3 C2 C1 121.32(12) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 121.04(13) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 119.89(12) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.47(12) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C7 C6 C5 121.43(12) . . ? C7 C6 C1 119.63(11) . . ? C5 C6 C1 118.93(12) . . ? C6 C7 C8 121.96(11) . . ? C6 C7 H7 119.0 . . ? C8 C7 H7 119.0 . . ? C7 C8 C9 121.24(11) . . ? C7 C8 C13 119.38(12) . . ? C9 C8 C13 119.38(12) . . ? C10 C9 C8 121.04(12) . . ? C10 C9 H9 119.5 . . ? C8 C9 H9 119.5 . . ? C9 C10 C11 120.09(13) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C12 C11 C10 120.93(12) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C11 C12 C13 121.23(12) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C14 C13 C12 123.41(11) . . ? C14 C13 C8 119.25(11) . . ? C12 C13 C8 117.33(11) . . ? C1 C14 C13 120.81(11) . . ? C1 C14 C15 120.48(11) . . ? C13 C14 C15 118.56(10) . . ? N1 C15 C14 114.35(9) . . ? N1 C15 H15A 108.7 . . ? C14 C15 H15A 108.7 . . ? N1 C15 H15B 108.7 . . ? C14 C15 H15B 108.7 . . ? H15A C15 H15B 107.6 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 N1 110.13(9) . . ? C18 C17 H17A 109.6 . . ? N1 C17 H17A 109.6 . . ? C18 C17 H17B 109.6 . . ? N1 C17 H17B 109.6 . . ? H17A C17 H17B 108.1 . . ? C19 C18 C23 121.15(10) . . ? C19 C18 C17 119.62(11) . . ? C23 C18 C17 119.23(10) . . ? C20 C19 C18 120.34(12) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C21 C20 C19 119.54(11) . . ? C21 C20 H20 120.2 . . ? C19 C20 H20 120.2 . . ? C20 C21 C22 120.07(12) . . ? C20 C21 H21 120.0 . . ? C22 C21 H21 120.0 . . ? C21 C22 C23 122.09(12) . . ? C21 C22 H22 119.0 . . ? C23 C22 H22 119.0 . . ? C22 C23 C18 116.80(10) . . ? C22 C23 B1 121.16(10) . . ? C18 C23 B1 122.03(10) . . ? O1 C24 H24A 109.5 . . ? O1 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O1 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O3 C25 C26 127.80(11) . . ? O3 C25 C30 110.84(10) . . ? C26 C25 C30 121.36(11) . . ? C25 C26 C27 117.34(13) . . ? C25 C26 H26 121.3 . . ? C27 C26 H26 121.3 . . ? C28 C27 C26 121.51(13) . . ? C28 C27 H27 119.2 . . ? C26 C27 H27 119.2 . . ? C27 C28 C29 120.99(12) . . ? C27 C28 H28 119.5 . . ? C29 C28 H28 119.5 . . ? C30 C29 C28 117.77(13) . . ? C30 C29 H29 121.1 . . ? C28 C29 H29 121.1 . . ? O2 C30 C29 127.95(12) . . ? O2 C30 C25 111.03(10) . . ? C29 C30 C25 121.00(12) . . ? O1 B1 O3 111.37(9) . . ? O1 B1 O2 109.49(9) . . ? O3 B1 O2 103.19(9) . . ? O1 B1 C23 106.92(9) . . ? O3 B1 C23 112.52(9) . . ? O2 B1 C23 113.40(9) . . ? C16 N1 C15 112.85(9) . . ? C16 N1 C17 111.45(9) . . ? C15 N1 C17 109.16(9) . . ? C16 N1 H1N 104.2(9) . . ? C15 N1 H1N 112.5(9) . . ? C17 N1 H1N 106.4(9) . . ? C24 O1 B1 116.43(9) . . ? C30 O2 B1 107.09(9) . . ? C25 O3 B1 107.28(9) . . ? 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 C14 C1 C2 C3 -179.98(11) . . . . ? C6 C1 C2 C3 -0.67(17) . . . . ? C1 C2 C3 C4 0.02(19) . . . . ? C2 C3 C4 C5 0.8(2) . . . . ? C3 C4 C5 C6 -0.9(2) . . . . ? C4 C5 C6 C7 179.96(12) . . . . ? C4 C5 C6 C1 0.24(19) . . . . ? C14 C1 C6 C7 0.16(17) . . . . ? C2 C1 C6 C7 -179.19(11) . . . . ? C14 C1 C6 C5 179.88(11) . . . . ? C2 C1 C6 C5 0.54(16) . . . . ? C5 C6 C7 C8 -179.96(12) . . . . ? C1 C6 C7 C8 -0.24(18) . . . . ? C6 C7 C8 C9 179.15(11) . . . . ? C6 C7 C8 C13 -0.51(18) . . . . ? C7 C8 C9 C10 -179.71(12) . . . . ? C13 C8 C9 C10 -0.05(18) . . . . ? C8 C9 C10 C11 0.07(19) . . . . ? C9 C10 C11 C12 -0.4(2) . . . . ? C10 C11 C12 C13 0.68(19) . . . . ? C11 C12 C13 C14 177.94(11) . . . . ? C11 C12 C13 C8 -0.64(17) . . . . ? C7 C8 C13 C14 1.34(17) . . . . ? C9 C8 C13 C14 -178.33(10) . . . . ? C7 C8 C13 C12 179.99(11) . . . . ? C9 C8 C13 C12 0.32(16) . . . . ? C2 C1 C14 C13 179.99(10) . . . . ? C6 C1 C14 C13 0.69(16) . . . . ? C2 C1 C14 C15 4.49(17) . . . . ? C6 C1 C14 C15 -174.81(10) . . . . ? C12 C13 C14 C1 180.00(10) . . . . ? C8 C13 C14 C1 -1.44(16) . . . . ? C12 C13 C14 C15 -4.41(16) . . . . ? C8 C13 C14 C15 174.15(10) . . . . ? C1 C14 C15 N1 -101.67(12) . . . . ? C13 C14 C15 N1 82.73(13) . . . . ? N1 C17 C18 C19 -105.57(11) . . . . ? N1 C17 C18 C23 74.91(13) . . . . ? C23 C18 C19 C20 -0.64(17) . . . . ? C17 C18 C19 C20 179.86(10) . . . . ? C18 C19 C20 C21 0.92(18) . . . . ? C19 C20 C21 C22 -0.19(19) . . . . ? C20 C21 C22 C23 -0.86(19) . . . . ? C21 C22 C23 C18 1.12(17) . . . . ? C21 C22 C23 B1 -177.74(11) . . . . ? C19 C18 C23 C22 -0.37(16) . . . . ? C17 C18 C23 C22 179.13(10) . . . . ? C19 C18 C23 B1 178.48(10) . . . . ? C17 C18 C23 B1 -2.02(16) . . . . ? O3 C25 C26 C27 178.21(11) . . . . ? C30 C25 C26 C27 -1.10(17) . . . . ? C25 C26 C27 C28 -0.19(18) . . . . ? C26 C27 C28 C29 0.8(2) . . . . ? C27 C28 C29 C30 -0.07(19) . . . . ? C28 C29 C30 O2 -179.57(11) . . . . ? C28 C29 C30 C25 -1.21(18) . . . . ? O3 C25 C30 O2 1.04(13) . . . . ? C26 C25 C30 O2 -179.54(10) . . . . ? O3 C25 C30 C29 -177.57(10) . . . . ? C26 C25 C30 C29 1.85(17) . . . . ? C22 C23 B1 O1 110.06(11) . . . . ? C18 C23 B1 O1 -68.74(13) . . . . ? C22 C23 B1 O3 -12.53(15) . . . . ? C18 C23 B1 O3 168.68(10) . . . . ? C22 C23 B1 O2 -129.17(11) . . . . ? C18 C23 B1 O2 52.03(14) . . . . ? C14 C15 N1 C16 70.53(12) . . . . ? C14 C15 N1 C17 -164.96(9) . . . . ? C18 C17 N1 C16 -156.66(10) . . . . ? C18 C17 N1 C15 78.02(11) . . . . ? O3 B1 O1 C24 -61.22(12) . . . . ? O2 B1 O1 C24 52.26(13) . . . . ? C23 B1 O1 C24 175.49(9) . . . . ? C29 C30 O2 B1 172.97(12) . . . . ? C25 C30 O2 B1 -5.52(12) . . . . ? O1 B1 O2 C30 -111.23(10) . . . . ? O3 B1 O2 C30 7.45(11) . . . . ? C23 B1 O2 C30 129.46(10) . . . . ? C26 C25 O3 B1 -175.39(11) . . . . ? C30 C25 O3 B1 3.98(12) . . . . ? O1 B1 O3 C25 110.52(10) . . . . ? O2 B1 O3 C25 -6.85(11) . . . . ? C23 B1 O3 C25 -129.44(9) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.302 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.032 # Attachment '1-8.cif' data_zhu25 _database_code_depnum_ccdc_archive 'CCDC 715265' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C30 H27 B N2 O5' _chemical_formula_sum 'C30 H27 B N2 O5' _chemical_formula_weight 506.35 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' 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 P2(1)/c _symmetry_space_group_name_Hall -P2ybc 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 10.7385(4) _cell_length_b 12.4075(5) _cell_length_c 19.1650(8) _cell_angle_alpha 90.00 _cell_angle_beta 105.615(2) _cell_angle_gamma 90.00 _cell_volume 2459.26(17) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9064 _cell_measurement_theta_min 2.21 _cell_measurement_theta_max 19.23 _exptl_crystal_description parallalpiped _exptl_crystal_colour yellow _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.368 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9835 _exptl_absorpt_correction_T_max 0.9844 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19127 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 19.26 _reflns_number_total 2044 _reflns_number_gt 1815 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0546P)^2^+2.7363P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2044 _refine_ls_number_parameters 349 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.1185 _refine_ls_wR_factor_gt 0.1143 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.2640(3) 0.5957(3) 0.52186(19) 0.0347(10) Uani 1 1 d . . . C2 C 0.2383(3) 0.6816(3) 0.5659(2) 0.0420(10) Uani 1 1 d . . . H2 H 0.2695 0.6764 0.6171 0.050 Uiso 1 1 calc R . . C3 C 0.1708(4) 0.7700(3) 0.5363(3) 0.0507(11) Uani 1 1 d . . . H3 H 0.1574 0.8267 0.5668 0.061 Uiso 1 1 calc R . . C4 C 0.1199(4) 0.7790(4) 0.4607(3) 0.0553(12) Uani 1 1 d . . . H4 H 0.0707 0.8406 0.4407 0.066 Uiso 1 1 calc R . . C5 C 0.1409(4) 0.7002(4) 0.4166(2) 0.0509(12) Uani 1 1 d . . . H5 H 0.1055 0.7069 0.3657 0.061 Uiso 1 1 calc R . . C6 C 0.2156(3) 0.6069(3) 0.4451(2) 0.0400(10) Uani 1 1 d . . . C7 C 0.2435(4) 0.5289(4) 0.4002(2) 0.0442(11) Uani 1 1 d . . . H7 H 0.2086 0.5360 0.3494 0.053 Uiso 1 1 calc R . . C8 C 0.3213(3) 0.4401(3) 0.4270(2) 0.0388(10) Uani 1 1 d . . . C9 C 0.3556(4) 0.3626(4) 0.3802(2) 0.0472(11) Uani 1 1 d . . . H9 H 0.3243 0.3710 0.3292 0.057 Uiso 1 1 calc R . . C10 C 0.4315(4) 0.2779(4) 0.4072(2) 0.0498(11) Uani 1 1 d . . . H10 H 0.4527 0.2271 0.3751 0.060 Uiso 1 1 calc R . . C11 C 0.4797(3) 0.2640(3) 0.4825(2) 0.0429(10) Uani 1 1 d . . . H11 H 0.5326 0.2035 0.5009 0.051 Uiso 1 1 calc R . . C12 C 0.4510(3) 0.3365(3) 0.5290(2) 0.0369(10) Uani 1 1 d . . . H12 H 0.4858 0.3263 0.5797 0.044 Uiso 1 1 calc R . . C13 C 0.3702(3) 0.4272(3) 0.50389(19) 0.0330(9) Uani 1 1 d . . . C14 C 0.3381(3) 0.5039(3) 0.55069(18) 0.0317(9) Uani 1 1 d . . . C15 C 0.3832(3) 0.4849(3) 0.63122(17) 0.0324(9) Uani 1 1 d . . . H15A H 0.3831 0.5538 0.6572 0.039 Uiso 1 1 calc R . . H15B H 0.4728 0.4568 0.6442 0.039 Uiso 1 1 calc R . . C16 C 0.1696(3) 0.4534(3) 0.6547(2) 0.0433(10) Uani 1 1 d . . . H16A H 0.1835 0.5090 0.6924 0.065 Uiso 1 1 calc R . . H16B H 0.1125 0.3974 0.6648 0.065 Uiso 1 1 calc R . . H16C H 0.1296 0.4860 0.6074 0.065 Uiso 1 1 calc R . . C17 C 0.3578(3) 0.3490(3) 0.72530(17) 0.0379(10) Uani 1 1 d . . . H17A H 0.3860 0.4037 0.7639 0.045 Uiso 1 1 calc R . . H17B H 0.2935 0.3017 0.7385 0.045 Uiso 1 1 calc R . . C18 C 0.4731(3) 0.2824(3) 0.72038(18) 0.0349(10) Uani 1 1 d . . . C19 C 0.5965(4) 0.3243(3) 0.75116(19) 0.0417(10) Uani 1 1 d . . . H19 H 0.6061 0.3903 0.7773 0.050 Uiso 1 1 calc R . . C20 C 0.7042(4) 0.2704(4) 0.7437(2) 0.0499(11) Uani 1 1 d . . . H20 H 0.7879 0.2987 0.7652 0.060 Uiso 1 1 calc R . . C21 C 0.6909(4) 0.1751(4) 0.7051(2) 0.0520(11) Uani 1 1 d . . . H21 H 0.7650 0.1387 0.6989 0.062 Uiso 1 1 calc R . . C22 C 0.5689(4) 0.1332(3) 0.6758(2) 0.0454(11) Uani 1 1 d . . . H22 H 0.5612 0.0670 0.6501 0.055 Uiso 1 1 calc R . . C23 C 0.4563(3) 0.1840(3) 0.68220(18) 0.0364(10) Uani 1 1 d . . . C24 C 0.2043(3) 0.1758(3) 0.5260(2) 0.0374(10) Uani 1 1 d . . . C25 C 0.1364(3) 0.2273(3) 0.4638(2) 0.0422(10) Uani 1 1 d . . . H25 H 0.0964 0.2954 0.4647 0.051 Uiso 1 1 calc R . . C26 C 0.1303(3) 0.1720(4) 0.3987(2) 0.0399(10) Uani 1 1 d . . . C27 C 0.1880(4) 0.0747(4) 0.3955(2) 0.0526(11) Uani 1 1 d . . . H27 H 0.1811 0.0413 0.3500 0.059(13) Uiso 1 1 calc R . . C28 C 0.2565(4) 0.0252(3) 0.4587(2) 0.0517(11) Uani 1 1 d . . . H28 H 0.2975 -0.0423 0.4575 0.062 Uiso 1 1 calc R . . C29 C 0.2638(4) 0.0769(3) 0.5243(2) 0.0433(11) Uani 1 1 d . . . C30 C 0.1344(4) 0.0491(3) 0.6797(2) 0.0554(12) Uani 1 1 d . . . H30A H 0.0719 0.1085 0.6711 0.083 Uiso 1 1 calc R . . H30B H 0.1209 0.0030 0.7186 0.083 Uiso 1 1 calc R . . H30C H 0.1222 0.0064 0.6354 0.083 Uiso 1 1 calc R . . B1 B 0.3166(4) 0.1306(3) 0.6455(2) 0.0402(12) Uani 1 1 d . . . O1 O 0.2258(2) 0.21249(18) 0.59515(13) 0.0393(7) Uani 1 1 d . . . O2 O 0.3265(2) 0.04342(19) 0.59058(15) 0.0484(7) Uani 1 1 d . . . O3 O 0.2616(2) 0.09131(19) 0.70023(12) 0.0444(7) Uani 1 1 d . . . N1 N 0.2953(3) 0.4049(2) 0.65410(15) 0.0324(8) Uani 1 1 d . . . H1N H 0.276(3) 0.351(3) 0.6187(18) 0.039 Uiso 1 1 d . . . N2 N 0.0634(3) 0.2247(3) 0.3313(2) 0.0553(10) Uani 1 1 d . . . O4 O 0.0138(3) 0.3145(3) 0.33473(14) 0.0658(9) Uani 1 1 d . . . O5 O 0.0552(3) 0.1774(3) 0.27304(15) 0.0651(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.032(2) 0.035(3) 0.036(3) 0.002(2) 0.007(2) -0.0109(19) C2 0.036(2) 0.040(3) 0.047(3) 0.011(3) 0.0067(19) -0.002(2) C3 0.045(3) 0.044(3) 0.063(4) 0.006(2) 0.015(2) -0.001(2) C4 0.037(3) 0.046(3) 0.078(4) 0.024(3) 0.007(3) 0.000(2) C5 0.038(3) 0.058(3) 0.049(3) 0.019(3) -0.001(2) -0.012(2) C6 0.034(2) 0.044(3) 0.038(3) 0.011(2) 0.002(2) -0.012(2) C7 0.043(2) 0.054(3) 0.030(2) 0.006(3) 0.000(2) -0.019(2) C8 0.039(2) 0.042(3) 0.034(3) -0.003(2) 0.008(2) -0.020(2) C9 0.048(3) 0.060(3) 0.032(2) -0.008(3) 0.009(2) -0.024(3) C10 0.047(3) 0.058(3) 0.048(3) -0.017(2) 0.019(2) -0.019(3) C11 0.040(2) 0.042(3) 0.048(3) -0.004(2) 0.015(2) -0.0098(19) C12 0.039(2) 0.039(3) 0.033(2) -0.002(2) 0.0096(19) -0.011(2) C13 0.033(2) 0.035(3) 0.030(3) 0.002(2) 0.0074(18) -0.011(2) C14 0.030(2) 0.032(2) 0.031(2) 0.004(2) 0.0048(18) -0.010(2) C15 0.033(2) 0.027(2) 0.037(2) 0.0022(18) 0.0093(18) -0.0049(18) C16 0.039(2) 0.042(2) 0.050(3) 0.007(2) 0.0154(19) 0.000(2) C17 0.048(2) 0.038(2) 0.026(2) 0.0040(18) 0.0061(18) -0.005(2) C18 0.037(3) 0.037(3) 0.028(2) 0.0103(19) 0.0048(18) 0.000(2) C19 0.043(3) 0.043(2) 0.035(2) 0.0074(19) 0.003(2) -0.003(2) C20 0.037(3) 0.057(3) 0.049(3) 0.017(2) -0.001(2) -0.006(2) C21 0.044(3) 0.052(3) 0.060(3) 0.020(3) 0.014(2) 0.011(2) C22 0.054(3) 0.036(2) 0.046(3) 0.012(2) 0.014(2) 0.006(2) C23 0.045(3) 0.033(2) 0.029(2) 0.011(2) 0.0070(18) 0.003(2) C24 0.035(2) 0.041(3) 0.032(3) -0.001(2) 0.002(2) -0.012(2) C25 0.034(2) 0.042(2) 0.048(3) 0.000(3) 0.009(2) -0.012(2) C26 0.036(2) 0.057(3) 0.022(3) -0.002(2) -0.0008(19) -0.013(2) C27 0.053(3) 0.050(3) 0.054(4) -0.012(3) 0.015(2) -0.011(2) C28 0.061(3) 0.043(3) 0.052(3) -0.008(3) 0.016(2) -0.010(2) C29 0.049(3) 0.037(3) 0.043(3) -0.001(3) 0.011(2) -0.013(2) C30 0.051(3) 0.059(3) 0.050(3) 0.011(2) 0.003(2) -0.013(2) B1 0.050(3) 0.031(3) 0.036(3) 0.005(2) 0.005(2) -0.001(2) O1 0.0457(16) 0.0340(15) 0.0335(17) 0.0008(13) 0.0027(12) -0.0054(12) O2 0.0650(18) 0.0346(16) 0.0424(19) 0.0009(14) 0.0088(15) -0.0005(13) O3 0.0472(17) 0.0427(16) 0.0391(16) 0.0057(13) 0.0041(13) -0.0089(13) N1 0.0374(19) 0.0304(19) 0.0281(19) 0.0008(15) 0.0067(15) -0.0022(16) N2 0.044(2) 0.064(3) 0.057(3) -0.004(3) 0.013(2) -0.008(2) O4 0.063(2) 0.076(2) 0.052(2) 0.0015(17) 0.0046(15) 0.0063(18) O5 0.069(2) 0.094(2) 0.0305(18) -0.0201(17) 0.0100(14) -0.0036(17) _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 C14 1.414(5) . ? C1 C6 1.428(5) . ? C1 C2 1.432(5) . ? C2 C3 1.353(5) . ? C2 H2 0.9500 . ? C3 C4 1.408(6) . ? C3 H3 0.9500 . ? C4 C5 1.350(6) . ? C4 H4 0.9500 . ? C5 C6 1.431(5) . ? C5 H5 0.9500 . ? C6 C7 1.381(5) . ? C7 C8 1.394(5) . ? C7 H7 0.9500 . ? C8 C9 1.429(5) . ? C8 C13 1.435(5) . ? C9 C10 1.344(5) . ? C9 H9 0.9500 . ? C10 C11 1.407(5) . ? C10 H10 0.9500 . ? C11 C12 1.360(5) . ? C11 H11 0.9500 . ? C12 C13 1.423(5) . ? C12 H12 0.9500 . ? C13 C14 1.413(5) . ? C14 C15 1.507(5) . ? C15 N1 1.513(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N1 1.482(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.512(5) . ? C17 N1 1.517(4) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.397(5) . ? C18 C23 1.411(5) . ? C19 C20 1.377(5) . ? C19 H19 0.9500 . ? C20 C21 1.382(6) . ? C20 H20 0.9500 . ? C21 C22 1.381(5) . ? C21 H21 0.9500 . ? C22 C23 1.398(5) . ? C22 H22 0.9500 . ? C23 B1 1.617(6) . ? C24 O1 1.360(4) . ? C24 C25 1.376(5) . ? C24 C29 1.388(5) . ? C25 C26 1.410(5) . ? C25 H25 0.9500 . ? C26 C27 1.367(5) . ? C26 N2 1.454(5) . ? C27 C28 1.380(5) . ? C27 H27 0.9500 . ? C28 C29 1.396(5) . ? C28 H28 0.9500 . ? C29 O2 1.334(4) . ? C30 O3 1.417(4) . ? C30 H30A 0.9800 . ? C30 H30B 0.9800 . ? C30 H30C 0.9800 . ? B1 O3 1.421(5) . ? B1 O2 1.532(5) . ? B1 O1 1.552(5) . ? N1 H1N 0.94(3) . ? N2 O5 1.243(4) . ? N2 O4 1.244(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C14 C1 C6 119.5(3) . . ? C14 C1 C2 123.1(3) . . ? C6 C1 C2 117.4(3) . . ? C3 C2 C1 121.5(4) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 120.8(4) . . ? C2 C3 H3 119.6 . . ? C4 C3 H3 119.6 . . ? C5 C4 C3 120.2(4) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 121.1(4) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C7 C6 C1 119.5(4) . . ? C7 C6 C5 121.5(4) . . ? C1 C6 C5 119.0(4) . . ? C6 C7 C8 122.3(4) . . ? C6 C7 H7 118.9 . . ? C8 C7 H7 118.9 . . ? C7 C8 C9 122.1(4) . . ? C7 C8 C13 118.9(4) . . ? C9 C8 C13 118.9(4) . . ? C10 C9 C8 121.1(4) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.6(4) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 120.4(4) . . ? C12 C11 H11 119.8 . . ? C10 C11 H11 119.8 . . ? C11 C12 C13 121.7(3) . . ? C11 C12 H12 119.1 . . ? C13 C12 H12 119.1 . . ? C14 C13 C12 123.3(3) . . ? C14 C13 C8 119.5(3) . . ? C12 C13 C8 117.2(3) . . ? C13 C14 C1 120.2(3) . . ? C13 C14 C15 118.6(3) . . ? C1 C14 C15 121.2(3) . . ? C14 C15 N1 110.3(3) . . ? C14 C15 H15A 109.6 . . ? N1 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? N1 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 N1 111.4(3) . . ? C18 C17 H17A 109.3 . . ? N1 C17 H17A 109.3 . . ? C18 C17 H17B 109.3 . . ? N1 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? C19 C18 C23 121.1(3) . . ? C19 C18 C17 118.0(4) . . ? C23 C18 C17 120.8(3) . . ? C20 C19 C18 120.2(4) . . ? C20 C19 H19 119.9 . . ? C18 C19 H19 119.9 . . ? C19 C20 C21 120.2(4) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C22 C21 C20 119.4(4) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 122.9(4) . . ? C21 C22 H22 118.6 . . ? C23 C22 H22 118.6 . . ? C22 C23 C18 116.3(3) . . ? C22 C23 B1 120.0(3) . . ? C18 C23 B1 123.7(3) . . ? O1 C24 C25 126.9(4) . . ? O1 C24 C29 111.1(3) . . ? C25 C24 C29 122.0(4) . . ? C24 C25 C26 115.3(4) . . ? C24 C25 H25 122.3 . . ? C26 C25 H25 122.3 . . ? C27 C26 C25 123.9(4) . . ? C27 C26 N2 118.6(4) . . ? C25 C26 N2 117.5(4) . . ? C26 C27 C28 119.6(4) . . ? C26 C27 H27 120.2 . . ? C28 C27 H27 120.2 . . ? C27 C28 C29 118.3(4) . . ? C27 C28 H28 120.8 . . ? C29 C28 H28 120.8 . . ? O2 C29 C24 111.8(3) . . ? O2 C29 C28 127.4(4) . . ? C24 C29 C28 120.9(4) . . ? O3 C30 H30A 109.5 . . ? O3 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O3 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? O3 B1 O2 112.6(3) . . ? O3 B1 O1 111.5(3) . . ? O2 B1 O1 100.6(3) . . ? O3 B1 C23 109.9(3) . . ? O2 B1 C23 111.1(3) . . ? O1 B1 C23 110.9(3) . . ? C24 O1 B1 107.5(3) . . ? C29 O2 B1 108.9(3) . . ? C30 O3 B1 118.9(3) . . ? C16 N1 C15 112.1(3) . . ? C16 N1 C17 111.2(3) . . ? C15 N1 C17 113.6(3) . . ? C16 N1 H1N 106(2) . . ? C15 N1 H1N 107(2) . . ? C17 N1 H1N 106(2) . . ? O5 N2 O4 122.8(4) . . ? O5 N2 C26 119.0(4) . . ? O4 N2 C26 118.1(4) . . ? 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 C14 C1 C2 C3 177.7(3) . . . . ? C6 C1 C2 C3 0.1(5) . . . . ? C1 C2 C3 C4 1.9(5) . . . . ? C2 C3 C4 C5 -1.7(6) . . . . ? C3 C4 C5 C6 -0.6(6) . . . . ? C14 C1 C6 C7 -1.0(5) . . . . ? C2 C1 C6 C7 176.6(3) . . . . ? C14 C1 C6 C5 -179.9(3) . . . . ? C2 C1 C6 C5 -2.2(5) . . . . ? C4 C5 C6 C7 -176.4(3) . . . . ? C4 C5 C6 C1 2.5(5) . . . . ? C1 C6 C7 C8 -2.0(5) . . . . ? C5 C6 C7 C8 176.8(3) . . . . ? C6 C7 C8 C9 -176.6(3) . . . . ? C6 C7 C8 C13 2.3(5) . . . . ? C7 C8 C9 C10 179.6(3) . . . . ? C13 C8 C9 C10 0.6(5) . . . . ? C8 C9 C10 C11 -0.4(5) . . . . ? C9 C10 C11 C12 -0.5(5) . . . . ? C10 C11 C12 C13 1.1(5) . . . . ? C11 C12 C13 C14 179.8(3) . . . . ? C11 C12 C13 C8 -0.8(5) . . . . ? C7 C8 C13 C14 0.4(5) . . . . ? C9 C8 C13 C14 179.3(3) . . . . ? C7 C8 C13 C12 -179.0(3) . . . . ? C9 C8 C13 C12 -0.1(4) . . . . ? C12 C13 C14 C1 176.0(3) . . . . ? C8 C13 C14 C1 -3.3(5) . . . . ? C12 C13 C14 C15 -4.6(5) . . . . ? C8 C13 C14 C15 176.0(3) . . . . ? C6 C1 C14 C13 3.6(5) . . . . ? C2 C1 C14 C13 -173.9(3) . . . . ? C6 C1 C14 C15 -175.7(3) . . . . ? C2 C1 C14 C15 6.8(5) . . . . ? C13 C14 C15 N1 -79.8(4) . . . . ? C1 C14 C15 N1 99.5(3) . . . . ? N1 C17 C18 C19 102.5(3) . . . . ? N1 C17 C18 C23 -73.9(4) . . . . ? C23 C18 C19 C20 0.9(5) . . . . ? C17 C18 C19 C20 -175.5(3) . . . . ? C18 C19 C20 C21 0.7(5) . . . . ? C19 C20 C21 C22 -1.7(5) . . . . ? C20 C21 C22 C23 1.1(6) . . . . ? C21 C22 C23 C18 0.5(5) . . . . ? C21 C22 C23 B1 179.3(3) . . . . ? C19 C18 C23 C22 -1.5(5) . . . . ? C17 C18 C23 C22 174.8(3) . . . . ? C19 C18 C23 B1 179.8(3) . . . . ? C17 C18 C23 B1 -3.9(5) . . . . ? O1 C24 C25 C26 179.0(3) . . . . ? C29 C24 C25 C26 0.8(5) . . . . ? C24 C25 C26 C27 -0.8(5) . . . . ? C24 C25 C26 N2 -177.9(3) . . . . ? C25 C26 C27 C28 0.3(6) . . . . ? N2 C26 C27 C28 177.4(3) . . . . ? C26 C27 C28 C29 0.2(6) . . . . ? O1 C24 C29 O2 0.0(4) . . . . ? C25 C24 C29 O2 178.5(3) . . . . ? O1 C24 C29 C28 -178.8(3) . . . . ? C25 C24 C29 C28 -0.2(5) . . . . ? C27 C28 C29 O2 -178.8(3) . . . . ? C27 C28 C29 C24 -0.3(5) . . . . ? C22 C23 B1 O3 110.2(4) . . . . ? C18 C23 B1 O3 -71.1(4) . . . . ? C22 C23 B1 O2 -15.0(5) . . . . ? C18 C23 B1 O2 163.6(3) . . . . ? C22 C23 B1 O1 -126.0(3) . . . . ? C18 C23 B1 O1 52.7(4) . . . . ? C25 C24 O1 B1 -175.3(3) . . . . ? C29 C24 O1 B1 3.2(4) . . . . ? O3 B1 O1 C24 -124.2(3) . . . . ? O2 B1 O1 C24 -4.6(3) . . . . ? C23 B1 O1 C24 113.0(3) . . . . ? C24 C29 O2 B1 -3.2(4) . . . . ? C28 C29 O2 B1 175.4(4) . . . . ? O3 B1 O2 C29 123.5(3) . . . . ? O1 B1 O2 C29 4.7(4) . . . . ? C23 B1 O2 C29 -112.8(3) . . . . ? O2 B1 O3 C30 -60.5(4) . . . . ? O1 B1 O3 C30 51.6(4) . . . . ? C23 B1 O3 C30 175.0(3) . . . . ? C14 C15 N1 C16 -74.8(4) . . . . ? C14 C15 N1 C17 158.0(3) . . . . ? C18 C17 N1 C16 169.6(3) . . . . ? C18 C17 N1 C15 -62.7(4) . . . . ? C27 C26 N2 O5 3.6(5) . . . . ? C25 C26 N2 O5 -179.2(3) . . . . ? C27 C26 N2 O4 -178.3(3) . . . . ? C25 C26 N2 O4 -1.1(5) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 19.26 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.416 _refine_diff_density_min -0.227 _refine_diff_density_rms 0.037 # Attachment '1-DCM.cif' data_zhu19 _database_code_depnum_ccdc_archive 'CCDC 715266' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H22 B N O2' _chemical_formula_sum 'C23 H22 B N O2' _chemical_formula_weight 355.23 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' 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 P2(1)/n _symmetry_space_group_name_Hall -P2yn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.8636(13) _cell_length_b 12.4780(16) _cell_length_c 15.734(2) _cell_angle_alpha 90.00 _cell_angle_beta 98.544(2) _cell_angle_gamma 90.00 _cell_volume 1915.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 6589 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.57 _exptl_crystal_description thin _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.232 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9302 _exptl_absorpt_correction_T_max 0.9939 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 22109 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0232 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 29.01 _reflns_number_total 4833 _reflns_number_gt 3868 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0478P)^2^+0.5218P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4833 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0517 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.1049 _refine_ls_wR_factor_gt 0.0975 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.84061(11) 0.70328(9) -0.09332(8) 0.0269(2) Uani 1 1 d . . . H1 H 0.8581 0.7348 -0.1456 0.032 Uiso 1 1 calc R . . C2 C 0.81746(12) 0.76720(9) -0.02740(8) 0.0306(3) Uani 1 1 d . . . H2 H 0.8183 0.8429 -0.0338 0.037 Uiso 1 1 calc R . . C3 C 0.79193(12) 0.72141(9) 0.05110(8) 0.0289(3) Uani 1 1 d . . . H3 H 0.7751 0.7669 0.0968 0.035 Uiso 1 1 calc R . . C4 C 0.79118(11) 0.61315(9) 0.06189(7) 0.0241(2) Uani 1 1 d . . . H4 H 0.7743 0.5846 0.1153 0.029 Uiso 1 1 calc R . . C5 C 0.81526(10) 0.54123(8) -0.00540(7) 0.0203(2) Uani 1 1 d . . . C6 C 0.83915(10) 0.58877(9) -0.08545(7) 0.0220(2) Uani 1 1 d . . . C7 C 0.86093(11) 0.52344(9) -0.15388(7) 0.0242(2) Uani 1 1 d . . . H7 H 0.8772 0.5554 -0.2062 0.029 Uiso 1 1 calc R . . C8 C 0.85940(11) 0.41195(9) -0.14723(7) 0.0231(2) Uani 1 1 d . . . C9 C 0.87774(12) 0.34452(10) -0.21806(8) 0.0288(3) Uani 1 1 d . . . H9 H 0.8919 0.3761 -0.2710 0.035 Uiso 1 1 calc R . . C10 C 0.87531(12) 0.23618(10) -0.21097(8) 0.0318(3) Uani 1 1 d . . . H10 H 0.8863 0.1927 -0.2591 0.038 Uiso 1 1 calc R . . C11 C 0.85654(12) 0.18767(10) -0.13225(8) 0.0304(3) Uani 1 1 d . . . H11 H 0.8555 0.1118 -0.1278 0.036 Uiso 1 1 calc R . . C12 C 0.83991(11) 0.24890(9) -0.06279(8) 0.0252(2) Uani 1 1 d . . . H12 H 0.8291 0.2148 -0.0102 0.030 Uiso 1 1 calc R . . C13 C 0.83843(10) 0.36346(8) -0.06743(7) 0.0210(2) Uani 1 1 d . . . C14 C 0.81655(10) 0.42832(8) 0.00286(7) 0.0197(2) Uani 1 1 d . . . C15 C 0.80223(11) 0.37521(9) 0.08721(7) 0.0210(2) Uani 1 1 d . . . H15A H 0.8778(13) 0.3233(10) 0.1017(8) 0.025 Uiso 1 1 d . . . H15B H 0.8153(13) 0.4288(11) 0.1356(8) 0.025 Uiso 1 1 d . . . N1 N 0.67233(9) 0.31583(7) 0.08840(6) 0.02004(19) Uani 1 1 d . . . C17 C 0.55215(11) 0.38476(9) 0.06326(8) 0.0279(3) Uani 1 1 d . . . H17A H 0.5564 0.4465 0.1021 0.042 Uiso 1 1 calc R . . H17B H 0.4683 0.3438 0.0667 0.042 Uiso 1 1 calc R . . H17C H 0.5516 0.4099 0.0042 0.042 Uiso 1 1 calc R . . C18 C 0.67034(11) 0.27375(9) 0.17624(7) 0.0230(2) Uani 1 1 d . . . H18A H 0.5809 0.2389 0.1790 0.028 Uiso 1 1 calc R . . H18B H 0.6805 0.3339 0.2177 0.028 Uiso 1 1 calc R . . C19 C 0.78425(11) 0.19372(8) 0.20120(7) 0.0209(2) Uani 1 1 d . . . C20 C 0.89473(12) 0.22272(9) 0.26287(7) 0.0248(2) Uani 1 1 d . . . H20 H 0.8945 0.2905 0.2903 0.030 Uiso 1 1 calc R . . C21 C 1.00506(12) 0.15383(10) 0.28473(8) 0.0292(3) Uani 1 1 d . . . H21 H 1.0800 0.1746 0.3266 0.035 Uiso 1 1 calc R . . C22 C 1.00507(12) 0.05480(10) 0.24510(8) 0.0313(3) Uani 1 1 d . . . H22 H 1.0812 0.0080 0.2586 0.038 Uiso 1 1 calc R . . C23 C 0.89366(12) 0.02395(9) 0.18554(8) 0.0281(3) Uani 1 1 d . . . H23 H 0.8937 -0.0451 0.1601 0.034 Uiso 1 1 calc R . . C24 C 0.78113(11) 0.09185(9) 0.16183(7) 0.0227(2) Uani 1 1 d . . . B1 B 0.65874(13) 0.05077(10) 0.09288(9) 0.0245(3) Uani 1 1 d . . . O1 O 0.62856(10) -0.05525(7) 0.09294(6) 0.0347(2) Uani 1 1 d . . . H1O H 0.5595(16) -0.0757(13) 0.0536(10) 0.042 Uiso 1 1 d . . . O2 O 0.58613(8) 0.11717(6) 0.03387(5) 0.0284(2) Uani 1 1 d . . . H2O H 0.6178(15) 0.1850(12) 0.0412(9) 0.034 Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0243(5) 0.0244(6) 0.0310(6) 0.0082(5) 0.0006(5) -0.0023(4) C2 0.0302(6) 0.0183(5) 0.0421(7) 0.0036(5) 0.0016(5) -0.0006(4) C3 0.0278(6) 0.0234(6) 0.0352(6) -0.0048(5) 0.0034(5) 0.0004(4) C4 0.0232(5) 0.0230(5) 0.0259(5) -0.0002(4) 0.0032(4) -0.0011(4) C5 0.0156(5) 0.0210(5) 0.0233(5) 0.0014(4) -0.0002(4) -0.0013(4) C6 0.0172(5) 0.0223(5) 0.0256(5) 0.0033(4) 0.0001(4) -0.0012(4) C7 0.0206(5) 0.0294(6) 0.0222(5) 0.0044(4) 0.0018(4) -0.0019(4) C8 0.0176(5) 0.0281(6) 0.0232(5) -0.0012(4) 0.0012(4) -0.0005(4) C9 0.0264(6) 0.0361(6) 0.0244(6) -0.0035(5) 0.0051(4) -0.0006(5) C10 0.0275(6) 0.0361(7) 0.0324(6) -0.0123(5) 0.0064(5) 0.0001(5) C11 0.0268(6) 0.0244(6) 0.0404(7) -0.0067(5) 0.0064(5) 0.0004(4) C12 0.0216(5) 0.0242(5) 0.0302(6) 0.0002(4) 0.0048(4) 0.0011(4) C13 0.0158(5) 0.0226(5) 0.0240(5) -0.0005(4) 0.0007(4) 0.0001(4) C14 0.0159(5) 0.0202(5) 0.0222(5) 0.0007(4) 0.0008(4) -0.0012(4) C15 0.0196(5) 0.0197(5) 0.0233(5) 0.0011(4) 0.0016(4) -0.0016(4) N1 0.0178(4) 0.0174(4) 0.0248(5) 0.0027(3) 0.0025(3) 0.0008(3) C17 0.0209(5) 0.0242(5) 0.0381(7) 0.0054(5) 0.0030(5) 0.0043(4) C18 0.0239(5) 0.0200(5) 0.0264(5) 0.0016(4) 0.0082(4) 0.0008(4) C19 0.0227(5) 0.0197(5) 0.0209(5) 0.0039(4) 0.0058(4) -0.0004(4) C20 0.0298(6) 0.0228(5) 0.0219(5) 0.0008(4) 0.0044(4) -0.0038(4) C21 0.0276(6) 0.0315(6) 0.0265(6) 0.0053(5) -0.0024(5) -0.0042(5) C22 0.0267(6) 0.0267(6) 0.0383(7) 0.0070(5) -0.0023(5) 0.0036(5) C23 0.0281(6) 0.0199(5) 0.0350(6) 0.0021(5) 0.0006(5) 0.0017(4) C24 0.0236(5) 0.0192(5) 0.0251(5) 0.0036(4) 0.0023(4) -0.0005(4) B1 0.0241(6) 0.0194(6) 0.0297(6) 0.0000(5) 0.0024(5) 0.0000(5) O1 0.0382(5) 0.0179(4) 0.0428(5) 0.0020(4) -0.0110(4) -0.0029(3) O2 0.0286(4) 0.0178(4) 0.0356(5) 0.0022(3) -0.0058(3) -0.0035(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 C2 1.3544(17) . ? C1 C6 1.4345(15) . ? C1 H1 0.9500 . ? C2 C3 1.4169(17) . ? C2 H2 0.9500 . ? C3 C4 1.3616(16) . ? C3 H3 0.9500 . ? C4 C5 1.4343(15) . ? C4 H4 0.9500 . ? C5 C14 1.4147(14) . ? C5 C6 1.4429(15) . ? C6 C7 1.3923(16) . ? C7 C8 1.3952(16) . ? C7 H7 0.9500 . ? C8 C9 1.4292(16) . ? C8 C13 1.4362(15) . ? C9 C10 1.3569(18) . ? C9 H9 0.9500 . ? C10 C11 1.4152(18) . ? C10 H10 0.9500 . ? C11 C12 1.3632(16) . ? C11 H11 0.9500 . ? C12 C13 1.4312(15) . ? C12 H12 0.9500 . ? C13 C14 1.4126(15) . ? C14 C15 1.5086(15) . ? C15 N1 1.4826(13) . ? C15 H15A 0.989(13) . ? C15 H15B 1.006(13) . ? N1 C17 1.4705(13) . ? N1 C18 1.4813(14) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.5108(15) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.3949(15) . ? C19 C24 1.4124(15) . ? C20 C21 1.3893(17) . ? C20 H20 0.9500 . ? C21 C22 1.3841(18) . ? C21 H21 0.9500 . ? C22 C23 1.3886(17) . ? C22 H22 0.9500 . ? C23 C24 1.4021(15) . ? C23 H23 0.9500 . ? C24 B1 1.5837(17) . ? B1 O1 1.3560(15) . ? B1 O2 1.3653(15) . ? O1 H1O 0.887(16) . ? O2 H2O 0.903(15) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 121.04(11) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C1 C2 C3 120.13(11) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 120.91(11) . . ? C4 C3 H3 119.5 . . ? C2 C3 H3 119.5 . . ? C3 C4 C5 121.61(11) . . ? C3 C4 H4 119.2 . . ? C5 C4 H4 119.2 . . ? C14 C5 C4 123.75(10) . . ? C14 C5 C6 119.29(10) . . ? C4 C5 C6 116.97(10) . . ? C7 C6 C1 120.79(10) . . ? C7 C6 C5 119.89(10) . . ? C1 C6 C5 119.33(10) . . ? C6 C7 C8 121.40(10) . . ? C6 C7 H7 119.3 . . ? C8 C7 H7 119.3 . . ? C7 C8 C9 121.63(11) . . ? C7 C8 C13 119.36(10) . . ? C9 C8 C13 119.01(10) . . ? C10 C9 C8 121.11(11) . . ? C10 C9 H9 119.4 . . ? C8 C9 H9 119.4 . . ? C9 C10 C11 120.28(11) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C12 C11 C10 120.58(11) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 121.37(11) . . ? C11 C12 H12 119.3 . . ? C13 C12 H12 119.3 . . ? C14 C13 C12 122.27(10) . . ? C14 C13 C8 120.10(10) . . ? C12 C13 C8 117.62(10) . . ? C13 C14 C5 119.94(10) . . ? C13 C14 C15 118.82(9) . . ? C5 C14 C15 121.16(10) . . ? N1 C15 C14 115.13(9) . . ? N1 C15 H15A 107.0(7) . . ? C14 C15 H15A 109.0(7) . . ? N1 C15 H15B 109.7(7) . . ? C14 C15 H15B 110.8(7) . . ? H15A C15 H15B 104.7(10) . . ? C17 N1 C18 109.66(8) . . ? C17 N1 C15 111.59(8) . . ? C18 N1 C15 108.68(8) . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 C19 111.37(8) . . ? N1 C18 H18A 109.4 . . ? C19 C18 H18A 109.4 . . ? N1 C18 H18B 109.4 . . ? C19 C18 H18B 109.4 . . ? H18A C18 H18B 108.0 . . ? C20 C19 C24 120.15(10) . . ? C20 C19 C18 118.91(10) . . ? C24 C19 C18 120.93(10) . . ? C21 C20 C19 120.93(11) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C20 119.56(11) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C23 119.90(11) . . ? C21 C22 H22 120.0 . . ? C23 C22 H22 120.0 . . ? C22 C23 C24 121.86(11) . . ? C22 C23 H23 119.1 . . ? C24 C23 H23 119.1 . . ? C23 C24 C19 117.55(10) . . ? C23 C24 B1 118.64(10) . . ? C19 C24 B1 123.81(10) . . ? O1 B1 O2 119.97(11) . . ? O1 B1 C24 117.41(10) . . ? O2 B1 C24 122.61(10) . . ? B1 O1 H1O 115.2(10) . . ? B1 O2 H2O 110.2(9) . . ? 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 C6 C1 C2 C3 0.32(17) . . . . ? C1 C2 C3 C4 0.48(18) . . . . ? C2 C3 C4 C5 -0.35(18) . . . . ? C3 C4 C5 C14 179.51(11) . . . . ? C3 C4 C5 C6 -0.54(16) . . . . ? C2 C1 C6 C7 179.01(10) . . . . ? C2 C1 C6 C5 -1.22(16) . . . . ? C14 C5 C6 C7 1.02(15) . . . . ? C4 C5 C6 C7 -178.93(10) . . . . ? C14 C5 C6 C1 -178.75(10) . . . . ? C4 C5 C6 C1 1.30(14) . . . . ? C1 C6 C7 C8 -179.81(10) . . . . ? C5 C6 C7 C8 0.42(16) . . . . ? C6 C7 C8 C9 178.16(10) . . . . ? C6 C7 C8 C13 -1.63(16) . . . . ? C7 C8 C9 C10 -179.64(11) . . . . ? C13 C8 C9 C10 0.15(17) . . . . ? C8 C9 C10 C11 -0.99(18) . . . . ? C9 C10 C11 C12 0.37(18) . . . . ? C10 C11 C12 C13 1.11(17) . . . . ? C11 C12 C13 C14 177.73(10) . . . . ? C11 C12 C13 C8 -1.90(16) . . . . ? C7 C8 C13 C14 1.41(15) . . . . ? C9 C8 C13 C14 -178.38(10) . . . . ? C7 C8 C13 C12 -178.95(10) . . . . ? C9 C8 C13 C12 1.26(15) . . . . ? C12 C13 C14 C5 -179.61(10) . . . . ? C8 C13 C14 C5 0.02(15) . . . . ? C12 C13 C14 C15 3.54(15) . . . . ? C8 C13 C14 C15 -176.84(9) . . . . ? C4 C5 C14 C13 178.73(10) . . . . ? C6 C5 C14 C13 -1.22(15) . . . . ? C4 C5 C14 C15 -4.49(15) . . . . ? C6 C5 C14 C15 175.56(9) . . . . ? C13 C14 C15 N1 -71.75(12) . . . . ? C5 C14 C15 N1 111.43(11) . . . . ? C14 C15 N1 C17 -55.83(12) . . . . ? C14 C15 N1 C18 -176.88(9) . . . . ? C17 N1 C18 C19 174.29(9) . . . . ? C15 N1 C18 C19 -63.49(11) . . . . ? N1 C18 C19 C20 108.87(11) . . . . ? N1 C18 C19 C24 -69.87(12) . . . . ? C24 C19 C20 C21 1.99(16) . . . . ? C18 C19 C20 C21 -176.76(10) . . . . ? C19 C20 C21 C22 -0.34(17) . . . . ? C20 C21 C22 C23 -1.62(18) . . . . ? C21 C22 C23 C24 1.96(19) . . . . ? C22 C23 C24 C19 -0.32(17) . . . . ? C22 C23 C24 B1 179.53(11) . . . . ? C20 C19 C24 C23 -1.63(16) . . . . ? C18 C19 C24 C23 177.09(10) . . . . ? C20 C19 C24 B1 178.52(10) . . . . ? C18 C19 C24 B1 -2.76(16) . . . . ? C23 C24 B1 O1 34.08(16) . . . . ? C19 C24 B1 O1 -146.07(11) . . . . ? C23 C24 B1 O2 -144.77(12) . . . . ? C19 C24 B1 O2 35.08(18) . . . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 29.01 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.334 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.038 # Attachment '1-MeOH.cif' data_zhu20 _database_code_depnum_ccdc_archive 'CCDC 715267' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H24 B N O2' _chemical_formula_sum 'C24 H24 B N O2' _chemical_formula_weight 369.25 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' O O 0.0106 0.0060 '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 _symmetry_space_group_name_Hall -P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.9127(3) _cell_length_b 10.3809(4) _cell_length_c 19.5778(7) _cell_angle_alpha 91.736(2) _cell_angle_beta 91.472(2) _cell_angle_gamma 101.463(2) _cell_volume 1972.48(12) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 9050 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 24.71 _exptl_crystal_description irregular _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9158 _exptl_absorpt_correction_T_max 0.9816 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 31551 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0277 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.71 _reflns_number_total 6723 _reflns_number_gt 5170 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0527P)^2^+0.3116P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0075(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6723 _refine_ls_number_parameters 516 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0929 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.20810(14) 0.76003(13) 0.01679(7) 0.0298(3) Uani 1 1 d . . . H1 H -0.1997 0.7848 0.0641 0.036 Uiso 1 1 calc R . . C2 C -0.32346(15) 0.77190(14) -0.01906(8) 0.0347(4) Uani 1 1 d . . . H2 H -0.3939 0.8052 0.0034 0.042 Uiso 1 1 calc R . . C3 C -0.34051(16) 0.73553(14) -0.08932(8) 0.0375(4) Uani 1 1 d . . . H3 H -0.4221 0.7440 -0.1138 0.045 Uiso 1 1 calc R . . C4 C -0.24036(16) 0.68852(14) -0.12176(8) 0.0356(4) Uani 1 1 d . . . H4 H -0.2528 0.6640 -0.1690 0.043 Uiso 1 1 calc R . . C5 C -0.11647(15) 0.67509(13) -0.08640(7) 0.0292(3) Uani 1 1 d . . . C6 C -0.01393(15) 0.62729(13) -0.12001(7) 0.0320(4) Uani 1 1 d . . . H6 H -0.0265 0.6044 -0.1674 0.038 Uiso 1 1 calc R . . C7 C 0.10690(15) 0.61193(13) -0.08620(7) 0.0290(3) Uani 1 1 d . . . C8 C 0.21048(16) 0.55922(14) -0.12024(8) 0.0359(4) Uani 1 1 d . . . H8 H 0.1971 0.5338 -0.1673 0.043 Uiso 1 1 calc R . . C9 C 0.32743(17) 0.54460(15) -0.08689(8) 0.0402(4) Uani 1 1 d . . . H9 H 0.3952 0.5093 -0.1105 0.048 Uiso 1 1 calc R . . C10 C 0.34835(16) 0.58210(14) -0.01682(8) 0.0373(4) Uani 1 1 d . . . H10 H 0.4310 0.5726 0.0063 0.045 Uiso 1 1 calc R . . C11 C 0.25221(15) 0.63139(13) 0.01789(8) 0.0317(3) Uani 1 1 d . . . H11 H 0.2687 0.6551 0.0651 0.038 Uiso 1 1 calc R . . C12 C 0.12682(14) 0.64847(13) -0.01475(7) 0.0273(3) Uani 1 1 d . . . C13 C 0.02396(14) 0.69715(13) 0.02046(7) 0.0259(3) Uani 1 1 d . . . C14 C -0.09831(14) 0.71112(13) -0.01455(7) 0.0267(3) Uani 1 1 d . . . C15 C 0.04619(14) 0.72682(13) 0.09667(7) 0.0271(3) Uani 1 1 d . . . H15A H -0.0441 0.7268 0.1172 0.032 Uiso 1 1 calc R . . H15B H 0.0851 0.6558 0.1174 0.032 Uiso 1 1 calc R . . C16 C 0.06638(16) 0.96276(14) 0.10312(8) 0.0377(4) Uani 1 1 d . . . H16A H 0.0307 0.9582 0.0558 0.057 Uiso 1 1 calc R . . H16B H 0.1301 1.0470 0.1122 0.057 Uiso 1 1 calc R . . H16C H -0.0103 0.9553 0.1343 0.057 Uiso 1 1 calc R . . C17 C 0.19002(15) 0.85939(14) 0.18567(7) 0.0315(3) Uani 1 1 d . . . H17A H 0.1102 0.8350 0.2153 0.038 Uiso 1 1 calc R . . H17B H 0.2357 0.9509 0.1985 0.038 Uiso 1 1 calc R . . C18 C 0.29019(14) 0.76976(14) 0.19935(7) 0.0284(3) Uani 1 1 d . . . C19 C 0.24753(16) 0.65861(15) 0.23728(7) 0.0334(4) Uani 1 1 d . . . H19 H 0.1554 0.6389 0.2521 0.040 Uiso 1 1 calc R . . C20 C 0.33639(17) 0.57628(15) 0.25388(7) 0.0389(4) Uani 1 1 d . . . H20 H 0.3049 0.5003 0.2793 0.047 Uiso 1 1 calc R . . C21 C 0.47108(17) 0.60478(16) 0.23336(8) 0.0399(4) Uani 1 1 d . . . H21 H 0.5333 0.5499 0.2454 0.048 Uiso 1 1 calc R . . C22 C 0.51412(16) 0.71421(15) 0.19501(7) 0.0347(4) Uani 1 1 d . . . H22 H 0.6067 0.7328 0.1808 0.042 Uiso 1 1 calc R . . C23 C 0.42682(14) 0.79852(14) 0.17634(7) 0.0283(3) Uani 1 1 d . . . C24 C 0.68549(16) 1.06501(15) 0.08889(8) 0.0391(4) Uani 1 1 d . . . H24A H 0.6668 1.0372 0.0407 0.059 Uiso 1 1 calc R . . H24B H 0.7852 1.0862 0.0982 0.059 Uiso 1 1 calc R . . H24C H 0.6465 1.1430 0.0988 0.059 Uiso 1 1 calc R . . B1 B 0.48455(17) 0.91425(16) 0.12794(8) 0.0288(4) Uani 1 1 d . . . O1 O 0.40517(11) 0.96491(10) 0.08345(5) 0.0359(3) Uani 1 1 d . . . H1O H 0.3134(17) 0.9236(16) 0.0843(8) 0.043 Uiso 1 1 d . . . O2 O 0.62377(10) 0.96035(9) 0.13147(5) 0.0337(3) Uani 1 1 d . . . N1 N 0.13924(11) 0.85451(11) 0.11375(6) 0.0277(3) Uani 1 1 d . . . C31 C 0.66192(16) 0.32148(15) 0.46588(7) 0.0378(4) Uani 1 1 d . . . H31 H 0.7252 0.3097 0.4317 0.045 Uiso 1 1 calc R . . C32 C 0.69372(19) 0.42614(16) 0.51060(8) 0.0456(4) Uani 1 1 d . . . H32 H 0.7784 0.4868 0.5070 0.055 Uiso 1 1 calc R . . C33 C 0.6029(2) 0.44615(17) 0.56226(8) 0.0491(5) Uani 1 1 d . . . H33 H 0.6262 0.5206 0.5928 0.059 Uiso 1 1 calc R . . C34 C 0.48316(19) 0.36017(17) 0.56849(8) 0.0442(4) Uani 1 1 d . . . H34 H 0.4235 0.3741 0.6040 0.053 Uiso 1 1 calc R . . C35 C 0.44435(16) 0.24854(15) 0.52269(7) 0.0358(4) Uani 1 1 d . . . C36 C 0.32260(16) 0.15781(16) 0.52904(7) 0.0381(4) Uani 1 1 d . . . H36 H 0.2630 0.1711 0.5647 0.046 Uiso 1 1 calc R . . C37 C 0.28460(15) 0.04821(15) 0.48521(7) 0.0334(4) Uani 1 1 d . . . C38 C 0.16068(16) -0.04594(16) 0.49425(8) 0.0401(4) Uani 1 1 d . . . H38 H 0.1033 -0.0330 0.5309 0.048 Uiso 1 1 calc R . . C39 C 0.12313(16) -0.15296(17) 0.45186(8) 0.0425(4) Uani 1 1 d . . . H39 H 0.0405 -0.2146 0.4589 0.051 Uiso 1 1 calc R . . C40 C 0.20741(16) -0.17264(16) 0.39709(8) 0.0396(4) Uani 1 1 d . . . H40 H 0.1804 -0.2476 0.3672 0.047 Uiso 1 1 calc R . . C41 C 0.32632(15) -0.08642(15) 0.38639(7) 0.0337(4) Uani 1 1 d . . . H41 H 0.3805 -0.1023 0.3489 0.040 Uiso 1 1 calc R . . C42 C 0.37263(15) 0.02814(14) 0.43008(7) 0.0299(3) Uani 1 1 d . . . C43 C 0.49724(15) 0.11884(14) 0.42262(7) 0.0300(3) Uani 1 1 d . . . C44 C 0.53489(15) 0.22852(14) 0.46910(7) 0.0324(4) Uani 1 1 d . . . C45 C 0.59639(15) 0.09951(14) 0.36764(7) 0.0316(3) Uani 1 1 d . . . H45A H 0.6896 0.1076 0.3889 0.038 Uiso 1 1 calc R . . H45B H 0.5684 0.0093 0.3474 0.038 Uiso 1 1 calc R . . C46 C 0.47130(16) 0.17596(17) 0.27369(8) 0.0435(4) Uani 1 1 d . . . H46A H 0.4757 0.2443 0.2399 0.065 Uiso 1 1 calc R . . H46B H 0.3973 0.1817 0.3052 0.065 Uiso 1 1 calc R . . H46C H 0.4529 0.0892 0.2502 0.065 Uiso 1 1 calc R . . C47 C 0.71394(15) 0.17882(16) 0.26527(7) 0.0363(4) Uani 1 1 d . . . H47A H 0.7107 0.2358 0.2259 0.044 Uiso 1 1 calc R . . H47B H 0.6971 0.0865 0.2475 0.044 Uiso 1 1 calc R . . C48 C 0.85587(15) 0.21291(15) 0.29921(7) 0.0336(4) Uani 1 1 d . . . C49 C 0.93020(17) 0.11333(16) 0.30693(8) 0.0438(4) Uani 1 1 d . . . H49 H 0.8913 0.0269 0.2899 0.053 Uiso 1 1 calc R . . C50 C 1.05926(18) 0.13724(18) 0.33880(10) 0.0527(5) Uani 1 1 d . . . H50 H 1.1077 0.0677 0.3439 0.063 Uiso 1 1 calc R . . C51 C 1.11709(18) 0.26208(18) 0.36308(10) 0.0522(5) Uani 1 1 d . . . H51 H 1.2047 0.2789 0.3860 0.063 Uiso 1 1 calc R . . C52 C 1.04678(16) 0.36321(17) 0.35385(8) 0.0419(4) Uani 1 1 d . . . H52 H 1.0892 0.4497 0.3694 0.050 Uiso 1 1 calc R . . C53 C 0.91543(15) 0.34259(15) 0.32243(7) 0.0334(4) Uani 1 1 d . . . C54 C 0.86628(18) 0.69780(16) 0.30227(9) 0.0485(4) Uani 1 1 d . . . H54A H 0.8402 0.7051 0.2541 0.073 Uiso 1 1 calc R . . H54B H 0.9334 0.7766 0.3176 0.073 Uiso 1 1 calc R . . H54C H 0.7843 0.6895 0.3300 0.073 Uiso 1 1 calc R . . B31 B 0.84191(18) 0.46313(17) 0.31505(8) 0.0323(4) Uani 1 1 d . . . O31 O 0.70428(10) 0.45409(11) 0.31365(5) 0.0363(3) Uani 1 1 d . . . H31O H 0.6567(16) 0.3697(17) 0.3205(8) 0.044 Uiso 1 1 d . . . O32 O 0.92615(10) 0.58419(10) 0.30968(6) 0.0416(3) Uani 1 1 d . . . N31 N 0.60294(12) 0.19490(12) 0.31223(6) 0.0316(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0289(8) 0.0262(8) 0.0324(8) -0.0001(6) -0.0009(6) 0.0013(6) C2 0.0290(8) 0.0283(8) 0.0459(9) 0.0008(7) -0.0012(7) 0.0038(6) C3 0.0327(9) 0.0304(8) 0.0467(9) 0.0022(7) -0.0130(7) 0.0011(7) C4 0.0405(9) 0.0282(8) 0.0349(8) -0.0017(7) -0.0102(7) 0.0012(7) C5 0.0328(8) 0.0215(7) 0.0309(8) 0.0017(6) -0.0024(6) 0.0000(6) C6 0.0415(9) 0.0256(8) 0.0262(7) -0.0003(6) 0.0006(7) 0.0004(7) C7 0.0330(8) 0.0204(7) 0.0310(8) 0.0010(6) 0.0051(7) -0.0014(6) C8 0.0436(10) 0.0271(8) 0.0357(8) -0.0012(6) 0.0107(7) 0.0030(7) C9 0.0380(10) 0.0287(8) 0.0547(10) -0.0008(7) 0.0167(8) 0.0070(7) C10 0.0309(9) 0.0280(8) 0.0530(10) 0.0003(7) 0.0027(7) 0.0061(7) C11 0.0305(8) 0.0238(8) 0.0393(8) -0.0008(6) -0.0012(7) 0.0024(6) C12 0.0277(8) 0.0175(7) 0.0348(8) 0.0013(6) 0.0018(6) 0.0001(6) C13 0.0273(8) 0.0199(7) 0.0284(7) 0.0013(6) 0.0001(6) 0.0000(6) C14 0.0286(8) 0.0187(7) 0.0308(8) 0.0022(6) -0.0005(6) 0.0001(6) C15 0.0261(8) 0.0240(7) 0.0301(8) 0.0008(6) -0.0002(6) 0.0027(6) C16 0.0354(9) 0.0262(8) 0.0501(10) -0.0007(7) -0.0073(7) 0.0041(7) C17 0.0284(8) 0.0345(8) 0.0301(8) -0.0061(6) -0.0007(6) 0.0038(7) C18 0.0305(8) 0.0315(8) 0.0218(7) -0.0046(6) -0.0040(6) 0.0039(6) C19 0.0328(8) 0.0398(9) 0.0246(7) 0.0001(6) -0.0011(6) 0.0005(7) C20 0.0479(10) 0.0367(9) 0.0292(8) 0.0073(7) -0.0041(7) 0.0011(8) C21 0.0435(10) 0.0386(9) 0.0391(9) 0.0073(7) -0.0070(7) 0.0118(8) C22 0.0318(8) 0.0374(9) 0.0346(8) 0.0016(7) -0.0016(7) 0.0066(7) C23 0.0298(8) 0.0294(8) 0.0246(7) -0.0039(6) -0.0048(6) 0.0045(6) C24 0.0408(9) 0.0322(9) 0.0411(9) 0.0015(7) 0.0050(7) -0.0008(7) B1 0.0305(9) 0.0285(9) 0.0272(8) -0.0056(7) -0.0011(7) 0.0064(7) O1 0.0319(6) 0.0359(6) 0.0390(6) 0.0083(5) -0.0018(5) 0.0037(5) O2 0.0311(6) 0.0325(6) 0.0351(6) 0.0030(4) 0.0001(4) 0.0002(5) N1 0.0276(7) 0.0230(6) 0.0315(6) -0.0012(5) -0.0050(5) 0.0034(5) C31 0.0423(10) 0.0419(9) 0.0292(8) 0.0033(7) -0.0052(7) 0.0087(8) C32 0.0561(11) 0.0407(10) 0.0363(9) 0.0015(7) -0.0109(8) 0.0021(8) C33 0.0706(13) 0.0418(10) 0.0343(9) -0.0074(7) -0.0110(9) 0.0126(9) C34 0.0576(12) 0.0469(10) 0.0312(8) -0.0044(7) -0.0017(8) 0.0191(9) C35 0.0451(10) 0.0391(9) 0.0265(8) -0.0003(7) -0.0024(7) 0.0171(8) C36 0.0409(10) 0.0477(10) 0.0304(8) 0.0014(7) 0.0041(7) 0.0197(8) C37 0.0337(9) 0.0402(9) 0.0297(8) 0.0048(7) 0.0007(7) 0.0155(7) C38 0.0330(9) 0.0539(11) 0.0369(9) 0.0066(8) 0.0057(7) 0.0155(8) C39 0.0324(9) 0.0481(10) 0.0460(10) 0.0081(8) 0.0010(7) 0.0050(8) C40 0.0393(9) 0.0387(9) 0.0400(9) 0.0004(7) -0.0023(7) 0.0066(8) C41 0.0349(9) 0.0374(9) 0.0305(8) 0.0022(7) 0.0000(7) 0.0110(7) C42 0.0314(8) 0.0351(8) 0.0258(7) 0.0031(6) -0.0015(6) 0.0132(7) C43 0.0322(8) 0.0345(8) 0.0251(7) 0.0037(6) -0.0013(6) 0.0109(7) C44 0.0377(9) 0.0349(9) 0.0265(7) 0.0040(6) -0.0045(6) 0.0123(7) C45 0.0319(8) 0.0336(8) 0.0286(8) 0.0009(6) -0.0006(6) 0.0056(7) C46 0.0370(9) 0.0547(11) 0.0355(9) 0.0055(8) -0.0089(7) 0.0019(8) C47 0.0409(9) 0.0394(9) 0.0261(8) -0.0018(6) 0.0041(7) 0.0022(7) C48 0.0341(9) 0.0389(9) 0.0280(8) 0.0013(6) 0.0078(6) 0.0069(7) C49 0.0451(10) 0.0374(9) 0.0507(10) 0.0022(8) 0.0137(8) 0.0109(8) C50 0.0408(11) 0.0491(11) 0.0745(13) 0.0166(9) 0.0129(9) 0.0209(9) C51 0.0330(10) 0.0552(12) 0.0704(12) 0.0148(9) -0.0009(9) 0.0120(9) C52 0.0323(9) 0.0424(10) 0.0497(10) 0.0050(8) -0.0002(7) 0.0044(7) C53 0.0306(8) 0.0391(9) 0.0305(8) 0.0041(7) 0.0052(6) 0.0059(7) C54 0.0444(10) 0.0354(9) 0.0662(12) 0.0036(8) 0.0110(9) 0.0079(8) B31 0.0313(10) 0.0382(10) 0.0262(9) 0.0006(7) 0.0000(7) 0.0046(8) O31 0.0310(6) 0.0345(6) 0.0433(6) 0.0068(5) -0.0006(5) 0.0058(5) O32 0.0342(6) 0.0337(6) 0.0565(7) 0.0027(5) 0.0046(5) 0.0053(5) N31 0.0310(7) 0.0376(7) 0.0246(6) 0.0015(5) -0.0032(5) 0.0039(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.355(2) . ? C1 C14 1.433(2) . ? C1 H1 0.9500 . ? C2 C3 1.412(2) . ? C2 H2 0.9500 . ? C3 C4 1.354(2) . ? C3 H3 0.9500 . ? C4 C5 1.427(2) . ? C4 H4 0.9500 . ? C5 C6 1.388(2) . ? C5 C14 1.4421(19) . ? C6 C7 1.393(2) . ? C6 H6 0.9500 . ? C7 C8 1.426(2) . ? C7 C12 1.4365(19) . ? C8 C9 1.353(2) . ? C8 H8 0.9500 . ? C9 C10 1.413(2) . ? C9 H9 0.9500 . ? C10 C11 1.356(2) . ? C10 H10 0.9500 . ? C11 C12 1.428(2) . ? C11 H11 0.9500 . ? C12 C13 1.411(2) . ? C13 C14 1.4117(19) . ? C13 C15 1.5158(18) . ? C15 N1 1.4802(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 N1 1.4686(18) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 N1 1.4791(17) . ? C17 C18 1.514(2) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.391(2) . ? C18 C23 1.416(2) . ? C19 C20 1.383(2) . ? C19 H19 0.9500 . ? C20 C21 1.382(2) . ? C20 H20 0.9500 . ? C21 C22 1.383(2) . ? C21 H21 0.9500 . ? C22 C23 1.397(2) . ? C22 H22 0.9500 . ? C23 B1 1.579(2) . ? C24 O2 1.4376(17) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? B1 O1 1.3459(19) . ? B1 O2 1.3672(19) . ? O1 H1O 0.926(17) . ? C31 C32 1.356(2) . ? C31 C44 1.430(2) . ? C31 H31 0.9500 . ? C32 C33 1.409(2) . ? C32 H32 0.9500 . ? C33 C34 1.347(2) . ? C33 H33 0.9500 . ? C34 C35 1.427(2) . ? C34 H34 0.9500 . ? C35 C36 1.386(2) . ? C35 C44 1.435(2) . ? C36 C37 1.388(2) . ? C36 H36 0.9500 . ? C37 C38 1.428(2) . ? C37 C42 1.441(2) . ? C38 C39 1.351(2) . ? C38 H38 0.9500 . ? C39 C40 1.411(2) . ? C39 H39 0.9500 . ? C40 C41 1.356(2) . ? C40 H40 0.9500 . ? C41 C42 1.435(2) . ? C41 H41 0.9500 . ? C42 C43 1.410(2) . ? C43 C44 1.419(2) . ? C43 C45 1.511(2) . ? C45 N31 1.4848(18) . ? C45 H45A 0.9900 . ? C45 H45B 0.9900 . ? C46 N31 1.4660(18) . ? C46 H46A 0.9800 . ? C46 H46B 0.9800 . ? C46 H46C 0.9800 . ? C47 N31 1.4830(19) . ? C47 C48 1.512(2) . ? C47 H47A 0.9900 . ? C47 H47B 0.9900 . ? C48 C49 1.393(2) . ? C48 C53 1.415(2) . ? C49 C50 1.382(2) . ? C49 H49 0.9500 . ? C50 C51 1.374(3) . ? C50 H50 0.9500 . ? C51 C52 1.384(2) . ? C51 H51 0.9500 . ? C52 C53 1.400(2) . ? C52 H52 0.9500 . ? C53 B31 1.577(2) . ? C54 O32 1.4312(19) . ? C54 H54A 0.9800 . ? C54 H54B 0.9800 . ? C54 H54C 0.9800 . ? B31 O31 1.348(2) . ? B31 O32 1.372(2) . ? O31 H31O 0.924(17) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C14 121.88(14) . . ? C2 C1 H1 119.1 . . ? C14 C1 H1 119.1 . . ? C1 C2 C3 120.96(15) . . ? C1 C2 H2 119.5 . . ? C3 C2 H2 119.5 . . ? C4 C3 C2 119.89(14) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C3 C4 C5 121.30(14) . . ? C3 C4 H4 119.3 . . ? C5 C4 H4 119.3 . . ? C6 C5 C4 121.03(13) . . ? C6 C5 C14 119.67(13) . . ? C4 C5 C14 119.29(13) . . ? C5 C6 C7 121.88(13) . . ? C5 C6 H6 119.1 . . ? C7 C6 H6 119.1 . . ? C6 C7 C8 121.90(13) . . ? C6 C7 C12 119.02(13) . . ? C8 C7 C12 119.07(13) . . ? C9 C8 C7 121.42(14) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 119.71(14) . . ? C8 C9 H9 120.1 . . ? C10 C9 H9 120.1 . . ? C11 C10 C9 121.01(15) . . ? C11 C10 H10 119.5 . . ? C9 C10 H10 119.5 . . ? C10 C11 C12 121.57(14) . . ? C10 C11 H11 119.2 . . ? C12 C11 H11 119.2 . . ? C13 C12 C11 122.71(13) . . ? C13 C12 C7 120.07(13) . . ? C11 C12 C7 117.21(13) . . ? C12 C13 C14 120.10(12) . . ? C12 C13 C15 118.05(12) . . ? C14 C13 C15 121.77(12) . . ? C13 C14 C1 124.08(13) . . ? C13 C14 C5 119.24(13) . . ? C1 C14 C5 116.67(12) . . ? N1 C15 C13 113.53(11) . . ? N1 C15 H15A 108.9 . . ? C13 C15 H15A 108.9 . . ? N1 C15 H15B 108.9 . . ? C13 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C17 C18 114.05(11) . . ? N1 C17 H17A 108.7 . . ? C18 C17 H17A 108.7 . . ? N1 C17 H17B 108.7 . . ? C18 C17 H17B 108.7 . . ? H17A C17 H17B 107.6 . . ? C19 C18 C23 119.47(13) . . ? C19 C18 C17 118.85(13) . . ? C23 C18 C17 121.65(13) . . ? C20 C19 C18 121.40(14) . . ? C20 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? C21 C20 C19 119.88(14) . . ? C21 C20 H20 120.1 . . ? C19 C20 H20 120.1 . . ? C20 C21 C22 119.19(15) . . ? C20 C21 H21 120.4 . . ? C22 C21 H21 120.4 . . ? C21 C22 C23 122.58(15) . . ? C21 C22 H22 118.7 . . ? C23 C22 H22 118.7 . . ? C22 C23 C18 117.45(13) . . ? C22 C23 B1 117.91(13) . . ? C18 C23 B1 124.55(13) . . ? O2 C24 H24A 109.5 . . ? O2 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O2 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? O1 B1 O2 120.00(14) . . ? O1 B1 C23 123.59(13) . . ? O2 B1 C23 116.38(13) . . ? B1 O1 H1O 112.3(10) . . ? B1 O2 C24 120.20(12) . . ? C16 N1 C17 109.46(11) . . ? C16 N1 C15 110.08(11) . . ? C17 N1 C15 110.48(10) . . ? C32 C31 C44 121.26(15) . . ? C32 C31 H31 119.4 . . ? C44 C31 H31 119.4 . . ? C31 C32 C33 120.94(16) . . ? C31 C32 H32 119.5 . . ? C33 C32 H32 119.5 . . ? C34 C33 C32 120.25(16) . . ? C34 C33 H33 119.9 . . ? C32 C33 H33 119.9 . . ? C33 C34 C35 121.14(16) . . ? C33 C34 H34 119.4 . . ? C35 C34 H34 119.4 . . ? C36 C35 C34 121.93(15) . . ? C36 C35 C44 119.00(14) . . ? C34 C35 C44 119.06(15) . . ? C35 C36 C37 122.37(14) . . ? C35 C36 H36 118.8 . . ? C37 C36 H36 118.8 . . ? C36 C37 C38 121.20(14) . . ? C36 C37 C42 119.42(14) . . ? C38 C37 C42 119.38(14) . . ? C39 C38 C37 121.54(15) . . ? C39 C38 H38 119.2 . . ? C37 C38 H38 119.2 . . ? C38 C39 C40 119.60(15) . . ? C38 C39 H39 120.2 . . ? C40 C39 H39 120.2 . . ? C41 C40 C39 121.18(15) . . ? C41 C40 H40 119.4 . . ? C39 C40 H40 119.4 . . ? C40 C41 C42 121.87(14) . . ? C40 C41 H41 119.1 . . ? C42 C41 H41 119.1 . . ? C43 C42 C41 124.27(13) . . ? C43 C42 C37 119.31(13) . . ? C41 C42 C37 116.42(13) . . ? C42 C43 C44 120.04(13) . . ? C42 C43 C45 121.55(13) . . ? C44 C43 C45 118.36(13) . . ? C43 C44 C31 122.85(14) . . ? C43 C44 C35 119.83(14) . . ? C31 C44 C35 117.31(14) . . ? N31 C45 C43 113.55(12) . . ? N31 C45 H45A 108.9 . . ? C43 C45 H45A 108.9 . . ? N31 C45 H45B 108.9 . . ? C43 C45 H45B 108.9 . . ? H45A C45 H45B 107.7 . . ? N31 C46 H46A 109.5 . . ? N31 C46 H46B 109.5 . . ? H46A C46 H46B 109.5 . . ? N31 C46 H46C 109.5 . . ? H46A C46 H46C 109.5 . . ? H46B C46 H46C 109.5 . . ? N31 C47 C48 112.97(11) . . ? N31 C47 H47A 109.0 . . ? C48 C47 H47A 109.0 . . ? N31 C47 H47B 109.0 . . ? C48 C47 H47B 109.0 . . ? H47A C47 H47B 107.8 . . ? C49 C48 C53 119.37(14) . . ? C49 C48 C47 118.64(14) . . ? C53 C48 C47 121.98(13) . . ? C50 C49 C48 121.58(16) . . ? C50 C49 H49 119.2 . . ? C48 C49 H49 119.2 . . ? C51 C50 C49 119.70(16) . . ? C51 C50 H50 120.1 . . ? C49 C50 H50 120.1 . . ? C50 C51 C52 119.55(16) . . ? C50 C51 H51 120.2 . . ? C52 C51 H51 120.2 . . ? C51 C52 C53 122.36(16) . . ? C51 C52 H52 118.8 . . ? C53 C52 H52 118.8 . . ? C52 C53 C48 117.38(14) . . ? C52 C53 B31 118.96(14) . . ? C48 C53 B31 123.66(13) . . ? O32 C54 H54A 109.5 . . ? O32 C54 H54B 109.5 . . ? H54A C54 H54B 109.5 . . ? O32 C54 H54C 109.5 . . ? H54A C54 H54C 109.5 . . ? H54B C54 H54C 109.5 . . ? O31 B31 O32 119.12(14) . . ? O31 B31 C53 124.42(14) . . ? O32 B31 C53 116.46(13) . . ? B31 O31 H31O 112.7(10) . . ? B31 O32 C54 119.44(12) . . ? C46 N31 C47 109.58(11) . . ? C46 N31 C45 110.98(11) . . ? C47 N31 C45 109.73(11) . . ? 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 C14 C1 C2 C3 0.3(2) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 -179.75(13) . . . . ? C3 C4 C5 C14 0.6(2) . . . . ? C4 C5 C6 C7 -179.18(13) . . . . ? C14 C5 C6 C7 0.4(2) . . . . ? C5 C6 C7 C8 178.13(13) . . . . ? C5 C6 C7 C12 -1.0(2) . . . . ? C6 C7 C8 C9 -179.94(14) . . . . ? C12 C7 C8 C9 -0.9(2) . . . . ? C7 C8 C9 C10 0.0(2) . . . . ? C8 C9 C10 C11 0.7(2) . . . . ? C9 C10 C11 C12 -0.5(2) . . . . ? C10 C11 C12 C13 178.75(13) . . . . ? C10 C11 C12 C7 -0.4(2) . . . . ? C6 C7 C12 C13 1.00(19) . . . . ? C8 C7 C12 C13 -178.12(12) . . . . ? C6 C7 C12 C11 -179.87(12) . . . . ? C8 C7 C12 C11 1.01(19) . . . . ? C11 C12 C13 C14 -179.61(12) . . . . ? C7 C12 C13 C14 -0.53(19) . . . . ? C11 C12 C13 C15 -2.59(19) . . . . ? C7 C12 C13 C15 176.49(11) . . . . ? C12 C13 C14 C1 -179.77(12) . . . . ? C15 C13 C14 C1 3.3(2) . . . . ? C12 C13 C14 C5 0.02(19) . . . . ? C15 C13 C14 C5 -176.89(12) . . . . ? C2 C1 C14 C13 179.85(13) . . . . ? C2 C1 C14 C5 0.06(19) . . . . ? C6 C5 C14 C13 0.04(19) . . . . ? C4 C5 C14 C13 179.67(12) . . . . ? C6 C5 C14 C1 179.84(12) . . . . ? C4 C5 C14 C1 -0.52(18) . . . . ? C12 C13 C15 N1 79.89(15) . . . . ? C14 C13 C15 N1 -103.14(14) . . . . ? N1 C17 C18 C19 -109.27(14) . . . . ? N1 C17 C18 C23 72.71(17) . . . . ? C23 C18 C19 C20 0.9(2) . . . . ? C17 C18 C19 C20 -177.17(13) . . . . ? C18 C19 C20 C21 0.8(2) . . . . ? C19 C20 C21 C22 -1.4(2) . . . . ? C20 C21 C22 C23 0.5(2) . . . . ? C21 C22 C23 C18 1.2(2) . . . . ? C21 C22 C23 B1 -175.57(13) . . . . ? C19 C18 C23 C22 -1.83(19) . . . . ? C17 C18 C23 C22 176.18(12) . . . . ? C19 C18 C23 B1 174.69(12) . . . . ? C17 C18 C23 B1 -7.3(2) . . . . ? C22 C23 B1 O1 150.26(14) . . . . ? C18 C23 B1 O1 -26.2(2) . . . . ? C22 C23 B1 O2 -27.80(19) . . . . ? C18 C23 B1 O2 155.70(13) . . . . ? O1 B1 O2 C24 1.4(2) . . . . ? C23 B1 O2 C24 179.57(12) . . . . ? C18 C17 N1 C16 -168.60(12) . . . . ? C18 C17 N1 C15 70.03(15) . . . . ? C13 C15 N1 C16 76.31(14) . . . . ? C13 C15 N1 C17 -162.69(11) . . . . ? C44 C31 C32 C33 0.6(2) . . . . ? C31 C32 C33 C34 0.8(3) . . . . ? C32 C33 C34 C35 -1.0(2) . . . . ? C33 C34 C35 C36 178.88(15) . . . . ? C33 C34 C35 C44 -0.2(2) . . . . ? C34 C35 C36 C37 -179.32(14) . . . . ? C44 C35 C36 C37 -0.3(2) . . . . ? C35 C36 C37 C38 177.97(14) . . . . ? C35 C36 C37 C42 -1.2(2) . . . . ? C36 C37 C38 C39 -179.90(15) . . . . ? C42 C37 C38 C39 -0.7(2) . . . . ? C37 C38 C39 C40 -0.3(2) . . . . ? C38 C39 C40 C41 0.5(2) . . . . ? C39 C40 C41 C42 0.3(2) . . . . ? C40 C41 C42 C43 178.00(14) . . . . ? C40 C41 C42 C37 -1.2(2) . . . . ? C36 C37 C42 C43 1.3(2) . . . . ? C38 C37 C42 C43 -177.87(13) . . . . ? C36 C37 C42 C41 -179.40(13) . . . . ? C38 C37 C42 C41 1.38(19) . . . . ? C41 C42 C43 C44 -179.19(13) . . . . ? C37 C42 C43 C44 0.0(2) . . . . ? C41 C42 C43 C45 -1.9(2) . . . . ? C37 C42 C43 C45 177.31(12) . . . . ? C42 C43 C44 C31 177.72(13) . . . . ? C45 C43 C44 C31 0.3(2) . . . . ? C42 C43 C44 C35 -1.5(2) . . . . ? C45 C43 C44 C35 -178.87(12) . . . . ? C32 C31 C44 C43 179.11(14) . . . . ? C32 C31 C44 C35 -1.7(2) . . . . ? C36 C35 C44 C43 1.6(2) . . . . ? C34 C35 C44 C43 -179.29(13) . . . . ? C36 C35 C44 C31 -177.63(13) . . . . ? C34 C35 C44 C31 1.5(2) . . . . ? C42 C43 C45 N31 109.57(15) . . . . ? C44 C43 C45 N31 -73.07(16) . . . . ? N31 C47 C48 C49 114.54(15) . . . . ? N31 C47 C48 C53 -66.22(18) . . . . ? C53 C48 C49 C50 2.1(2) . . . . ? C47 C48 C49 C50 -178.60(14) . . . . ? C48 C49 C50 C51 -0.6(3) . . . . ? C49 C50 C51 C52 -1.6(3) . . . . ? C50 C51 C52 C53 2.2(3) . . . . ? C51 C52 C53 C48 -0.7(2) . . . . ? C51 C52 C53 B31 179.06(15) . . . . ? C49 C48 C53 C52 -1.5(2) . . . . ? C47 C48 C53 C52 179.29(13) . . . . ? C49 C48 C53 B31 178.80(14) . . . . ? C47 C48 C53 B31 -0.4(2) . . . . ? C52 C53 B31 O31 -150.87(15) . . . . ? C48 C53 B31 O31 28.8(2) . . . . ? C52 C53 B31 O32 29.2(2) . . . . ? C48 C53 B31 O32 -151.05(14) . . . . ? O31 B31 O32 C54 -0.4(2) . . . . ? C53 B31 O32 C54 179.48(13) . . . . ? C48 C47 N31 C46 173.04(13) . . . . ? C48 C47 N31 C45 -64.86(15) . . . . ? C43 C45 N31 C46 -65.40(16) . . . . ? C43 C45 N31 C47 173.35(12) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.71 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.236 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.033