# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Hiromitsu Maeda' _publ_contact_author_email maedahir@ph.ritsumei.ac.jp loop_ _publ_author_name Y.Bando S.Sakamoto I.Yamada Y.Haketa H.Maeda data_90113 _database_code_depnum_ccdc_archive 'CCDC 852919' #TrackingRef '2b_1.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C32 H33 B F2 N2 O11' _chemical_formula_weight 670.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2xc' _symmetry_Int_Tables_number 14 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 10.818(2) _cell_length_b 20.488(6) _cell_length_c 14.235(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.575(8) _cell_angle_gamma 90.00 _cell_volume 3151.9(13) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1400 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9667 _exptl_absorpt_correction_T_max 0.9887 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\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 30398 _diffrn_reflns_av_R_equivalents 0.0463 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 27.49 _reflns_number_total 7164 _reflns_number_gt 5418 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0526P)^2^+1.6714P] 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 7164 _refine_ls_number_parameters 439 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0658 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1180 _refine_ls_wR_factor_gt 0.1080 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _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 O1 O 0.26733(14) 0.54665(6) 0.72154(9) 0.0318(3) Uani 1 1 d . . . O2 O 0.22101(15) 0.64598(6) 0.81102(9) 0.0320(3) Uani 1 1 d . . . B1 B 0.2340(2) 0.61682(11) 0.71708(14) 0.0268(5) Uani 1 1 d . . . F1 F 0.12294(12) 0.62312(6) 0.66689(8) 0.0366(3) Uani 1 1 d . . . F2 F 0.32587(12) 0.64949(6) 0.67283(8) 0.0371(3) Uani 1 1 d . . . N1 N 0.30867(14) 0.41635(7) 0.70816(10) 0.0197(3) Uani 1 1 d . . . H1 H 0.2965 0.4358 0.6534 0.024 Uiso 1 1 calc R . . N2 N 0.19164(14) 0.71064(7) 0.97720(10) 0.0204(3) Uani 1 1 d . . . H2 H 0.2028 0.7372 0.9297 0.024 Uiso 1 1 calc R . . O3 O 0.27813(12) 0.16692(6) 0.96731(10) 0.0278(3) Uani 1 1 d . . . O4 O 0.10987(11) 0.22482(6) 0.99961(9) 0.0248(3) Uani 1 1 d . . . O5 O 0.12556(13) 0.39778(7) 1.08464(10) 0.0311(3) Uani 1 1 d . . . O6 O 0.20081(12) 0.30472(7) 1.14752(9) 0.0267(3) Uani 1 1 d . . . O7 O 0.40867(12) 0.49816(6) 1.15279(9) 0.0275(3) Uani 1 1 d . . . O8 O 0.31399(12) 0.46462(6) 1.28128(9) 0.0230(3) Uani 1 1 d . . . O9 O 0.25584(14) 0.66826(7) 1.39629(9) 0.0325(3) Uani 1 1 d . . . O10 O 0.38299(12) 0.58630(6) 1.36404(8) 0.0250(3) Uani 1 1 d . . . C1 C 0.33463(16) 0.35203(8) 0.72021(12) 0.0206(4) Uani 1 1 d . . . H3 H 0.3426 0.3208 0.6716 0.025 Uiso 1 1 calc R . . C2 C 0.34743(16) 0.34002(8) 0.81537(12) 0.0181(3) Uani 1 1 d . . . C3 C 0.32909(15) 0.39893(8) 0.86257(11) 0.0164(3) Uani 1 1 d . . . C4 C 0.30414(15) 0.44671(8) 0.79451(11) 0.0170(3) Uani 1 1 d . . . C5 C 0.27383(15) 0.51434(8) 0.80115(11) 0.0172(3) Uani 1 1 d . . . C6 C 0.25092(16) 0.54474(8) 0.88510(12) 0.0192(3) Uani 1 1 d . . . H4 H 0.2550 0.5203 0.9418 0.023 Uiso 1 1 calc R . . C7 C 0.22211(15) 0.61027(8) 0.88758(11) 0.0171(3) Uani 1 1 d . . . C8 C 0.19546(15) 0.64321(8) 0.97248(12) 0.0172(3) Uani 1 1 d . . . C9 C 0.17071(15) 0.62028(8) 1.06154(11) 0.0168(3) Uani 1 1 d . . . C10 C 0.15291(15) 0.67440(8) 1.11917(12) 0.0188(3) Uani 1 1 d . . . C11 C 0.16812(16) 0.72983(9) 1.06600(12) 0.0208(4) Uani 1 1 d . . . H5 H 0.1631 0.7736 1.0876 0.025 Uiso 1 1 calc R . . C12 C 0.38179(16) 0.28397(8) 0.87911(12) 0.0194(3) Uani 1 1 d . . . H6 H 0.3888 0.2418 0.8445 0.023 Uiso 1 1 calc R . . C13 C 0.50526(17) 0.30407(9) 0.93262(14) 0.0252(4) Uani 1 1 d . . . H7 H 0.5299 0.2700 0.9790 0.030 Uiso 1 1 calc R . . H8 H 0.5718 0.3083 0.8875 0.030 Uiso 1 1 calc R . . C14 C 0.48717(16) 0.36980(9) 0.98353(13) 0.0239(4) Uani 1 1 d . . . H9 H 0.5445 0.4028 0.9592 0.029 Uiso 1 1 calc R . . H10 H 0.5065 0.3644 1.0517 0.029 Uiso 1 1 calc R . . C15 C 0.35067(16) 0.39380(8) 0.96738(11) 0.0180(3) Uani 1 1 d . . . H11 H 0.3343 0.4357 1.0006 0.022 Uiso 1 1 calc R . . C16 C 0.28568(15) 0.28154(8) 0.95423(11) 0.0174(3) Uani 1 1 d . . . C17 C 0.22558(15) 0.21874(8) 0.97457(11) 0.0176(3) Uani 1 1 d . . . C18 C 0.05064(17) 0.16505(10) 1.02757(14) 0.0282(4) Uani 1 1 d . . . H12 H 0.0361 0.1370 0.9724 0.042 Uiso 1 1 calc R . . H13 H -0.0285 0.1753 1.0550 0.042 Uiso 1 1 calc R . . H14 H 0.1042 0.1423 1.0743 0.042 Uiso 1 1 calc R . . C19 C 0.27123(15) 0.33782(8) 1.00053(11) 0.0173(3) Uani 1 1 d . . . C20 C 0.18991(16) 0.35043(9) 1.08043(12) 0.0197(3) Uani 1 1 d . . . C21 C 0.1172(2) 0.31243(11) 1.22363(14) 0.0356(5) Uani 1 1 d . . . H15 H 0.1378 0.3525 1.2584 0.053 Uiso 1 1 calc R . . H16 H 0.1255 0.2749 1.2662 0.053 Uiso 1 1 calc R . . H17 H 0.0319 0.3150 1.1977 0.053 Uiso 1 1 calc R . . C22 C 0.15159(15) 0.55630(8) 1.11030(11) 0.0178(3) Uani 1 1 d . . . H18 H 0.1677 0.5179 1.0692 0.021 Uiso 1 1 calc R . . C23 C 0.01615(16) 0.55766(9) 1.14438(12) 0.0232(4) Uani 1 1 d . . . H19 H -0.0430 0.5603 1.0894 0.028 Uiso 1 1 calc R . . H20 H -0.0008 0.5170 1.1791 0.028 Uiso 1 1 calc R . . C24 C -0.00120(17) 0.61739(10) 1.20923(13) 0.0262(4) Uani 1 1 d . . . H21 H -0.0240 0.6024 1.2723 0.031 Uiso 1 1 calc R . . H22 H -0.0689 0.6453 1.1829 0.031 Uiso 1 1 calc R . . C25 C 0.12114(16) 0.65743(9) 1.21779(12) 0.0210(4) Uani 1 1 d . . . H23 H 0.1143 0.6968 1.2588 0.025 Uiso 1 1 calc R . . C26 C 0.23533(16) 0.55747(8) 1.19936(11) 0.0179(3) Uani 1 1 d . . . C27 C 0.32976(16) 0.50480(8) 1.20906(11) 0.0178(3) Uani 1 1 d . . . C28 C 0.4115(2) 0.41651(10) 1.29527(14) 0.0318(5) Uani 1 1 d . . . H24 H 0.4185 0.3908 1.2377 0.048 Uiso 1 1 calc R . . H25 H 0.3917 0.3875 1.3472 0.048 Uiso 1 1 calc R . . H26 H 0.4901 0.4387 1.3103 0.048 Uiso 1 1 calc R . . C29 C 0.22007(16) 0.60983(8) 1.25459(12) 0.0184(3) Uani 1 1 d . . . C30 C 0.28677(16) 0.62476(8) 1.34455(12) 0.0192(3) Uani 1 1 d . . . C31 C 0.44642(19) 0.59678(10) 1.45483(13) 0.0295(4) Uani 1 1 d . . . H27 H 0.4847 0.6401 1.4561 0.044 Uiso 1 1 calc R . . H28 H 0.5105 0.5634 1.4651 0.044 Uiso 1 1 calc R . . H29 H 0.3868 0.5939 1.5045 0.044 Uiso 1 1 calc R . . O11 O 0.27159(14) 0.03521(7) 0.02032(10) 0.0321(3) Uani 1 1 d . . . H30 H 0.2665 0.0710 -0.0084 0.048 Uiso 1 1 calc R . . C32 C 0.1671(2) -0.00294(12) -0.00361(18) 0.0413(5) Uani 1 1 d . . . H31 H 0.1841 -0.0486 0.0128 0.062 Uiso 1 1 calc R . . H32 H 0.1477 0.0005 -0.0713 0.062 Uiso 1 1 calc R . . H33 H 0.0966 0.0126 0.0310 0.062 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0587(10) 0.0202(7) 0.0166(6) 0.0039(5) 0.0033(6) 0.0129(6) O2 0.0601(10) 0.0162(6) 0.0200(6) 0.0041(5) 0.0053(6) 0.0098(6) B1 0.0414(13) 0.0205(10) 0.0187(9) 0.0055(8) 0.0039(9) 0.0094(9) F1 0.0426(7) 0.0334(7) 0.0334(6) -0.0020(5) -0.0037(5) 0.0132(5) F2 0.0468(7) 0.0271(6) 0.0385(7) 0.0055(5) 0.0152(6) 0.0081(5) N1 0.0263(8) 0.0167(7) 0.0164(7) 0.0008(5) 0.0027(6) 0.0021(6) N2 0.0259(8) 0.0135(7) 0.0214(7) 0.0007(6) -0.0028(6) 0.0024(6) O3 0.0306(7) 0.0146(6) 0.0390(8) 0.0025(5) 0.0124(6) 0.0018(5) O4 0.0188(6) 0.0192(6) 0.0367(7) 0.0061(5) 0.0040(5) 0.0000(5) O5 0.0395(8) 0.0213(7) 0.0335(7) 0.0025(6) 0.0130(6) 0.0072(6) O6 0.0304(7) 0.0301(7) 0.0201(6) 0.0078(5) 0.0060(5) 0.0047(6) O7 0.0300(7) 0.0274(7) 0.0258(7) 0.0047(5) 0.0098(6) 0.0079(6) O8 0.0267(7) 0.0198(6) 0.0229(6) 0.0055(5) 0.0043(5) 0.0042(5) O9 0.0430(8) 0.0295(8) 0.0242(7) -0.0110(6) -0.0070(6) 0.0123(6) O10 0.0245(7) 0.0281(7) 0.0217(6) -0.0064(5) -0.0068(5) 0.0071(5) C1 0.0246(9) 0.0159(8) 0.0216(8) -0.0013(6) 0.0047(7) 0.0017(7) C2 0.0184(8) 0.0150(8) 0.0211(8) 0.0015(6) 0.0042(7) 0.0002(6) C3 0.0151(8) 0.0154(8) 0.0187(8) 0.0013(6) 0.0012(6) -0.0011(6) C4 0.0172(8) 0.0174(8) 0.0164(8) -0.0012(6) 0.0022(6) -0.0009(6) C5 0.0160(8) 0.0167(8) 0.0188(8) 0.0035(6) -0.0006(6) -0.0004(6) C6 0.0244(9) 0.0153(8) 0.0178(8) 0.0017(6) 0.0022(7) 0.0006(7) C7 0.0158(8) 0.0165(8) 0.0187(8) 0.0029(6) -0.0015(6) -0.0014(6) C8 0.0167(8) 0.0121(8) 0.0224(8) 0.0002(6) -0.0031(7) 0.0010(6) C9 0.0161(8) 0.0142(8) 0.0196(8) -0.0018(6) -0.0032(6) 0.0016(6) C10 0.0174(8) 0.0173(8) 0.0214(8) -0.0032(6) -0.0037(6) 0.0026(7) C11 0.0221(9) 0.0154(8) 0.0243(9) -0.0043(7) -0.0062(7) 0.0040(7) C12 0.0210(8) 0.0154(8) 0.0224(8) 0.0019(6) 0.0049(7) 0.0019(7) C13 0.0186(9) 0.0250(10) 0.0322(10) 0.0067(8) 0.0015(7) 0.0036(7) C14 0.0205(9) 0.0243(10) 0.0264(9) 0.0057(7) -0.0041(7) -0.0031(7) C15 0.0214(8) 0.0140(8) 0.0185(8) 0.0011(6) -0.0007(7) -0.0012(6) C16 0.0181(8) 0.0155(8) 0.0186(8) 0.0032(6) 0.0003(7) 0.0022(6) C17 0.0193(8) 0.0183(8) 0.0150(7) 0.0020(6) 0.0004(6) 0.0007(7) C18 0.0217(9) 0.0257(10) 0.0374(11) 0.0113(8) 0.0028(8) -0.0026(8) C19 0.0181(8) 0.0165(8) 0.0171(8) 0.0035(6) -0.0016(6) 0.0014(6) C20 0.0217(8) 0.0181(9) 0.0193(8) -0.0005(6) -0.0003(7) -0.0029(7) C21 0.0409(12) 0.0441(13) 0.0227(10) 0.0057(9) 0.0117(9) -0.0001(10) C22 0.0208(8) 0.0154(8) 0.0172(8) -0.0016(6) -0.0003(6) -0.0005(6) C23 0.0190(8) 0.0269(10) 0.0236(9) -0.0007(7) -0.0004(7) -0.0037(7) C24 0.0187(9) 0.0338(11) 0.0263(9) -0.0047(8) 0.0027(7) 0.0029(8) C25 0.0227(9) 0.0206(9) 0.0193(8) -0.0051(7) -0.0026(7) 0.0059(7) C26 0.0191(8) 0.0173(8) 0.0172(8) 0.0016(6) 0.0015(6) 0.0001(7) C27 0.0210(8) 0.0146(8) 0.0177(8) -0.0008(6) -0.0001(7) -0.0020(6) C28 0.0368(11) 0.0272(10) 0.0316(10) 0.0111(8) 0.0047(9) 0.0122(9) C29 0.0179(8) 0.0193(8) 0.0181(8) -0.0012(6) 0.0006(7) 0.0019(7) C30 0.0219(8) 0.0163(8) 0.0193(8) -0.0002(6) 0.0009(7) 0.0009(7) C31 0.0291(10) 0.0349(11) 0.0235(9) -0.0033(8) -0.0088(8) 0.0032(8) O11 0.0418(8) 0.0254(7) 0.0286(7) 0.0014(6) -0.0020(6) -0.0039(6) C32 0.0355(12) 0.0360(13) 0.0528(14) -0.0024(10) 0.0046(10) -0.0061(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C5 1.312(2) . ? O1 B1 1.483(2) . ? O2 C7 1.312(2) . ? O2 B1 1.477(2) . ? B1 F2 1.375(3) . ? B1 F1 1.376(3) . ? N1 C1 1.357(2) . ? N1 C4 1.381(2) . ? N1 H1 0.8800 . ? N2 C11 1.359(2) . ? N2 C8 1.384(2) . ? N2 H2 0.8800 . ? O3 C17 1.211(2) . ? O4 C17 1.323(2) . ? O4 C18 1.446(2) . ? O5 C20 1.197(2) . ? O6 C20 1.339(2) . ? O6 C21 1.451(2) . ? O7 C27 1.204(2) . ? O8 C27 1.334(2) . ? O8 C28 1.451(2) . ? O9 C30 1.213(2) . ? O10 C30 1.325(2) . ? O10 C31 1.452(2) . ? C1 C2 1.378(2) . ? C1 H3 0.9500 . ? C2 C3 1.400(2) . ? C2 C12 1.500(2) . ? C3 C4 1.395(2) . ? C3 C15 1.503(2) . ? C4 C5 1.428(2) . ? C5 C6 1.380(2) . ? C6 C7 1.379(2) . ? C6 H4 0.9500 . ? C7 C8 1.425(2) . ? C8 C9 1.389(2) . ? C9 C10 1.398(2) . ? C9 C22 1.502(2) . ? C10 C11 1.379(2) . ? C10 C25 1.501(2) . ? C11 H5 0.9500 . ? C12 C16 1.525(2) . ? C12 C13 1.563(3) . ? C12 H6 1.0000 . ? C13 C14 1.546(3) . ? C13 H7 0.9900 . ? C13 H8 0.9900 . ? C14 C15 1.564(2) . ? C14 H9 0.9900 . ? C14 H10 0.9900 . ? C15 C19 1.521(2) . ? C15 H11 1.0000 . ? C16 C19 1.341(2) . ? C16 C17 1.476(2) . ? C18 H12 0.9800 . ? C18 H13 0.9800 . ? C18 H14 0.9800 . ? C19 C20 1.491(2) . ? C21 H15 0.9800 . ? C21 H16 0.9800 . ? C21 H17 0.9800 . ? C22 C26 1.525(2) . ? C22 C23 1.564(2) . ? C22 H18 1.0000 . ? C23 C24 1.549(3) . ? C23 H19 0.9900 . ? C23 H20 0.9900 . ? C24 C25 1.557(3) . ? C24 H21 0.9900 . ? C24 H22 0.9900 . ? C25 C29 1.523(2) . ? C25 H23 1.0000 . ? C26 C29 1.344(2) . ? C26 C27 1.488(2) . ? C28 H24 0.9800 . ? C28 H25 0.9800 . ? C28 H26 0.9800 . ? C29 C30 1.473(2) . ? C31 H27 0.9800 . ? C31 H28 0.9800 . ? C31 H29 0.9800 . ? O11 C32 1.404(3) . ? O11 H30 0.8400 . ? C32 H31 0.9800 . ? C32 H32 0.9800 . ? C32 H33 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 C5 O1 B1 121.99(14) . . ? C7 O2 B1 121.91(15) . . ? F2 B1 F1 110.41(16) . . ? F2 B1 O2 108.54(18) . . ? F1 B1 O2 108.41(16) . . ? F2 B1 O1 108.19(16) . . ? F1 B1 O1 108.56(18) . . ? O2 B1 O1 112.73(15) . . ? C1 N1 C4 109.91(14) . . ? C1 N1 H1 125.0 . . ? C4 N1 H1 125.0 . . ? C11 N2 C8 109.96(14) . . ? C11 N2 H2 125.0 . . ? C8 N2 H2 125.0 . . ? C17 O4 C18 115.52(14) . . ? C20 O6 C21 114.75(15) . . ? C27 O8 C28 114.07(14) . . ? C30 O10 C31 115.72(14) . . ? N1 C1 C2 108.00(15) . . ? N1 C1 H3 126.0 . . ? C2 C1 H3 126.0 . . ? C1 C2 C3 107.93(15) . . ? C1 C2 C12 137.96(16) . . ? C3 C2 C12 113.98(15) . . ? C4 C3 C2 107.38(14) . . ? C4 C3 C15 139.02(15) . . ? C2 C3 C15 113.39(14) . . ? N1 C4 C3 106.77(14) . . ? N1 C4 C5 120.91(15) . . ? C3 C4 C5 132.27(15) . . ? O1 C5 C6 121.04(16) . . ? O1 C5 C4 115.85(15) . . ? C6 C5 C4 123.10(15) . . ? C7 C6 C5 120.75(16) . . ? C7 C6 H4 119.6 . . ? C5 C6 H4 119.6 . . ? O2 C7 C6 121.01(15) . . ? O2 C7 C8 116.46(15) . . ? C6 C7 C8 122.51(15) . . ? N2 C8 C9 106.61(14) . . ? N2 C8 C7 121.45(15) . . ? C9 C8 C7 131.94(16) . . ? C8 C9 C10 107.73(15) . . ? C8 C9 C22 138.85(15) . . ? C10 C9 C22 113.31(14) . . ? C11 C10 C9 107.95(15) . . ? C11 C10 C25 137.92(16) . . ? C9 C10 C25 114.11(15) . . ? N2 C11 C10 107.72(15) . . ? N2 C11 H5 126.1 . . ? C10 C11 H5 126.1 . . ? C2 C12 C16 106.90(14) . . ? C2 C12 C13 106.03(14) . . ? C16 C12 C13 105.16(14) . . ? C2 C12 H6 112.7 . . ? C16 C12 H6 112.7 . . ? C13 C12 H6 112.7 . . ? C14 C13 C12 109.55(14) . . ? C14 C13 H7 109.8 . . ? C12 C13 H7 109.8 . . ? C14 C13 H8 109.8 . . ? C12 C13 H8 109.8 . . ? H7 C13 H8 108.2 . . ? C13 C14 C15 110.10(14) . . ? C13 C14 H9 109.6 . . ? C15 C14 H9 109.6 . . ? C13 C14 H10 109.6 . . ? C15 C14 H10 109.6 . . ? H9 C14 H10 108.2 . . ? C3 C15 C19 107.21(14) . . ? C3 C15 C14 105.75(14) . . ? C19 C15 C14 105.09(13) . . ? C3 C15 H11 112.7 . . ? C19 C15 H11 112.7 . . ? C14 C15 H11 112.7 . . ? C19 C16 C17 126.24(15) . . ? C19 C16 C12 114.51(15) . . ? C17 C16 C12 119.07(14) . . ? O3 C17 O4 124.00(16) . . ? O3 C17 C16 122.34(15) . . ? O4 C17 C16 113.65(14) . . ? O4 C18 H12 109.5 . . ? O4 C18 H13 109.5 . . ? H12 C18 H13 109.5 . . ? O4 C18 H14 109.5 . . ? H12 C18 H14 109.5 . . ? H13 C18 H14 109.5 . . ? C16 C19 C20 127.57(15) . . ? C16 C19 C15 114.59(14) . . ? C20 C19 C15 117.82(14) . . ? O5 C20 O6 124.32(16) . . ? O5 C20 C19 122.89(16) . . ? O6 C20 C19 112.74(15) . . ? O6 C21 H15 109.5 . . ? O6 C21 H16 109.5 . . ? H15 C21 H16 109.5 . . ? O6 C21 H17 109.5 . . ? H15 C21 H17 109.5 . . ? H16 C21 H17 109.5 . . ? C9 C22 C26 106.35(13) . . ? C9 C22 C23 106.15(14) . . ? C26 C22 C23 105.76(13) . . ? C9 C22 H18 112.7 . . ? C26 C22 H18 112.7 . . ? C23 C22 H18 112.7 . . ? C24 C23 C22 109.83(14) . . ? C24 C23 H19 109.7 . . ? C22 C23 H19 109.7 . . ? C24 C23 H20 109.7 . . ? C22 C23 H20 109.7 . . ? H19 C23 H20 108.2 . . ? C23 C24 C25 109.71(14) . . ? C23 C24 H21 109.7 . . ? C25 C24 H21 109.7 . . ? C23 C24 H22 109.7 . . ? C25 C24 H22 109.7 . . ? H21 C24 H22 108.2 . . ? C10 C25 C29 106.44(14) . . ? C10 C25 C24 106.16(14) . . ? C29 C25 C24 105.73(15) . . ? C10 C25 H23 112.7 . . ? C29 C25 H23 112.7 . . ? C24 C25 H23 112.7 . . ? C29 C26 C27 128.77(16) . . ? C29 C26 C22 114.50(15) . . ? C27 C26 C22 116.45(14) . . ? O7 C27 O8 124.18(16) . . ? O7 C27 C26 121.63(15) . . ? O8 C27 C26 114.08(14) . . ? O8 C28 H24 109.5 . . ? O8 C28 H25 109.5 . . ? H24 C28 H25 109.5 . . ? O8 C28 H26 109.5 . . ? H24 C28 H26 109.5 . . ? H25 C28 H26 109.5 . . ? C26 C29 C30 127.27(16) . . ? C26 C29 C25 114.37(15) . . ? C30 C29 C25 118.36(14) . . ? O9 C30 O10 123.06(16) . . ? O9 C30 C29 122.86(16) . . ? O10 C30 C29 114.08(14) . . ? O10 C31 H27 109.5 . . ? O10 C31 H28 109.5 . . ? H27 C31 H28 109.5 . . ? O10 C31 H29 109.5 . . ? H27 C31 H29 109.5 . . ? H28 C31 H29 109.5 . . ? C32 O11 H30 109.5 . . ? O11 C32 H31 109.5 . . ? O11 C32 H32 109.5 . . ? H31 C32 H32 109.5 . . ? O11 C32 H33 109.5 . . ? H31 C32 H33 109.5 . . ? H32 C32 H33 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 C7 O2 B1 F2 -128.80(18) . . . . ? C7 O2 B1 F1 111.24(19) . . . . ? C7 O2 B1 O1 -9.0(3) . . . . ? C5 O1 B1 F2 125.21(18) . . . . ? C5 O1 B1 F1 -114.95(19) . . . . ? C5 O1 B1 O2 5.2(3) . . . . ? C4 N1 C1 C2 -0.1(2) . . . . ? N1 C1 C2 C3 -0.2(2) . . . . ? N1 C1 C2 C12 -175.66(19) . . . . ? C1 C2 C3 C4 0.40(19) . . . . ? C12 C2 C3 C4 177.07(14) . . . . ? C1 C2 C3 C15 -175.35(14) . . . . ? C12 C2 C3 C15 1.3(2) . . . . ? C1 N1 C4 C3 0.32(19) . . . . ? C1 N1 C4 C5 -177.70(15) . . . . ? C2 C3 C4 N1 -0.44(18) . . . . ? C15 C3 C4 N1 173.61(19) . . . . ? C2 C3 C4 C5 177.27(18) . . . . ? C15 C3 C4 C5 -8.7(4) . . . . ? B1 O1 C5 C6 -0.7(3) . . . . ? B1 O1 C5 C4 178.57(17) . . . . ? N1 C4 C5 O1 -8.7(2) . . . . ? C3 C4 C5 O1 173.85(17) . . . . ? N1 C4 C5 C6 170.53(16) . . . . ? C3 C4 C5 C6 -6.9(3) . . . . ? O1 C5 C6 C7 -0.9(3) . . . . ? C4 C5 C6 C7 179.95(16) . . . . ? B1 O2 C7 C6 8.2(3) . . . . ? B1 O2 C7 C8 -173.44(17) . . . . ? C5 C6 C7 O2 -3.0(3) . . . . ? C5 C6 C7 C8 178.74(16) . . . . ? C11 N2 C8 C9 1.27(19) . . . . ? C11 N2 C8 C7 -178.21(15) . . . . ? O2 C7 C8 N2 -11.7(2) . . . . ? C6 C7 C8 N2 166.66(16) . . . . ? O2 C7 C8 C9 168.98(18) . . . . ? C6 C7 C8 C9 -12.7(3) . . . . ? N2 C8 C9 C10 -0.34(19) . . . . ? C7 C8 C9 C10 179.07(17) . . . . ? N2 C8 C9 C22 175.48(19) . . . . ? C7 C8 C9 C22 -5.1(4) . . . . ? C8 C9 C10 C11 -0.69(19) . . . . ? C22 C9 C10 C11 -177.69(15) . . . . ? C8 C9 C10 C25 178.19(14) . . . . ? C22 C9 C10 C25 1.2(2) . . . . ? C8 N2 C11 C10 -1.7(2) . . . . ? C9 C10 C11 N2 1.5(2) . . . . ? C25 C10 C11 N2 -177.01(19) . . . . ? C1 C2 C12 C16 -133.1(2) . . . . ? C3 C2 C12 C16 51.66(19) . . . . ? C1 C2 C12 C13 115.1(2) . . . . ? C3 C2 C12 C13 -60.16(18) . . . . ? C2 C12 C13 C14 55.81(18) . . . . ? C16 C12 C13 C14 -57.22(17) . . . . ? C12 C13 C14 C15 1.59(19) . . . . ? C4 C3 C15 C19 132.9(2) . . . . ? C2 C3 C15 C19 -53.25(18) . . . . ? C4 C3 C15 C14 -115.3(2) . . . . ? C2 C3 C15 C14 58.50(18) . . . . ? C13 C14 C15 C3 -57.91(17) . . . . ? C13 C14 C15 C19 55.33(17) . . . . ? C2 C12 C16 C19 -53.91(19) . . . . ? C13 C12 C16 C19 58.51(19) . . . . ? C2 C12 C16 C17 130.71(16) . . . . ? C13 C12 C16 C17 -116.87(16) . . . . ? C18 O4 C17 O3 5.8(2) . . . . ? C18 O4 C17 C16 -175.19(15) . . . . ? C19 C16 C17 O3 -143.14(19) . . . . ? C12 C16 C17 O3 31.7(2) . . . . ? C19 C16 C17 O4 37.9(2) . . . . ? C12 C16 C17 O4 -147.34(15) . . . . ? C17 C16 C19 C20 -1.8(3) . . . . ? C12 C16 C19 C20 -176.75(16) . . . . ? C17 C16 C19 C15 176.69(15) . . . . ? C12 C16 C19 C15 1.7(2) . . . . ? C3 C15 C19 C16 52.02(19) . . . . ? C14 C15 C19 C16 -60.17(18) . . . . ? C3 C15 C19 C20 -129.38(15) . . . . ? C14 C15 C19 C20 118.43(16) . . . . ? C21 O6 C20 O5 6.6(3) . . . . ? C21 O6 C20 C19 -175.91(16) . . . . ? C16 C19 C20 O5 -135.1(2) . . . . ? C15 C19 C20 O5 46.5(2) . . . . ? C16 C19 C20 O6 47.4(2) . . . . ? C15 C19 C20 O6 -131.03(16) . . . . ? C8 C9 C22 C26 130.5(2) . . . . ? C10 C9 C22 C26 -53.89(18) . . . . ? C8 C9 C22 C23 -117.2(2) . . . . ? C10 C9 C22 C23 58.42(18) . . . . ? C9 C22 C23 C24 -57.50(18) . . . . ? C26 C22 C23 C24 55.22(18) . . . . ? C22 C23 C24 C25 1.1(2) . . . . ? C11 C10 C25 C29 -129.3(2) . . . . ? C9 C10 C25 C29 52.34(19) . . . . ? C11 C10 C25 C24 118.4(2) . . . . ? C9 C10 C25 C24 -59.99(19) . . . . ? C23 C24 C25 C10 55.88(19) . . . . ? C23 C24 C25 C29 -56.94(18) . . . . ? C9 C22 C26 C29 53.47(18) . . . . ? C23 C22 C26 C29 -59.11(19) . . . . ? C9 C22 C26 C27 -120.98(16) . . . . ? C23 C22 C26 C27 126.44(15) . . . . ? C28 O8 C27 O7 8.4(3) . . . . ? C28 O8 C27 C26 -175.33(15) . . . . ? C29 C26 C27 O7 -113.1(2) . . . . ? C22 C26 C27 O7 60.5(2) . . . . ? C29 C26 C27 O8 70.5(2) . . . . ? C22 C26 C27 O8 -115.93(16) . . . . ? C27 C26 C29 C30 -6.4(3) . . . . ? C22 C26 C29 C30 180.00(16) . . . . ? C27 C26 C29 C25 174.18(16) . . . . ? C22 C26 C29 C25 0.6(2) . . . . ? C10 C25 C29 C26 -53.6(2) . . . . ? C24 C25 C29 C26 59.00(19) . . . . ? C10 C25 C29 C30 126.88(16) . . . . ? C24 C25 C29 C30 -120.50(16) . . . . ? C31 O10 C30 O9 3.4(3) . . . . ? C31 O10 C30 C29 -176.26(15) . . . . ? C26 C29 C30 O9 -169.53(18) . . . . ? C25 C29 C30 O9 9.9(3) . . . . ? C26 C29 C30 O10 10.2(3) . . . . ? C25 C29 C30 O10 -170.40(15) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.793 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.053 # Attachment '3a.CIF' data_00317mae _database_code_depnum_ccdc_archive 'CCDC 852920' #TrackingRef '3a.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C35 H25 B F2 N2 O2' _chemical_formula_sum 'C35 H25 B F2 N2 O2' _chemical_formula_weight 554.38 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.810(4) _cell_length_b 11.458(5) _cell_length_c 12.236(6) _cell_angle_alpha 101.958(18) _cell_angle_beta 107.036(17) _cell_angle_gamma 99.465(15) _cell_volume 1375.9(10) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.338 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9469 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\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 13561 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 27.47 _reflns_number_total 6228 _reflns_number_gt 4844 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'CrystalStructure 3.8' _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^)+(0.0467P)^2^+0.3168P] 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 6228 _refine_ls_number_parameters 379 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0574 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1039 _refine_ls_wR_factor_gt 0.0952 _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_restrained_S_all 1.055 _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 -0.19290(14) 0.72834(13) 0.05796(13) 0.0246(3) Uani 1 1 d . . . H1 H -0.2805 0.7394 0.0279 0.029 Uiso 1 1 calc R . . C2 C -0.15817(14) 0.64170(12) 0.11728(12) 0.0215(3) Uani 1 1 d . . . C3 C -0.01809(13) 0.65777(12) 0.14815(12) 0.0201(3) Uani 1 1 d . . . C4 C 0.02703(13) 0.75467(13) 0.10488(12) 0.0217(3) Uani 1 1 d . . . N1 N -0.08277(11) 0.79418(11) 0.04979(11) 0.0246(3) Uani 1 1 d . . . H2 H -0.0809 0.8537 0.0145 0.030 Uiso 1 1 calc R . . C5 C 0.15588(13) 0.81942(12) 0.11221(11) 0.0198(3) Uani 1 1 d . . . C6 C 0.27592(13) 0.81223(12) 0.18788(12) 0.0201(3) Uani 1 1 d . . . H3 H 0.2771 0.7627 0.2414 0.024 Uiso 1 1 calc R . . C7 C 0.39459(13) 0.87759(12) 0.18536(11) 0.0190(3) Uani 1 1 d . . . C8 C 0.52515(13) 0.87787(12) 0.25803(12) 0.0193(3) Uani 1 1 d . . . C9 C 0.57556(13) 0.84407(12) 0.36322(12) 0.0181(3) Uani 1 1 d . . . C10 C 0.71587(13) 0.87080(12) 0.39377(12) 0.0196(3) Uani 1 1 d . . . C11 C 0.74596(13) 0.91766(12) 0.30638(12) 0.0215(3) Uani 1 1 d . . . H4 H 0.8329 0.9419 0.3030 0.026 Uiso 1 1 calc R . . N2 N 0.63245(11) 0.92334(10) 0.22721(10) 0.0210(2) Uani 1 1 d . . . H5 H 0.6274 0.9519 0.1650 0.025 Uiso 1 1 calc R . . O1 O 0.15138(9) 0.89172(9) 0.04041(9) 0.0260(2) Uani 1 1 d . . . O2 O 0.39462(9) 0.94460(9) 0.10968(9) 0.0238(2) Uani 1 1 d . . . B1 B 0.27279(16) 0.97630(15) 0.04530(14) 0.0234(3) Uani 1 1 d . . . F1 F 0.27083(9) 0.96911(9) -0.06924(8) 0.0352(2) Uani 1 1 d . . . F2 F 0.27200(9) 1.09431(8) 0.10038(9) 0.0355(2) Uani 1 1 d . . . C12 C -0.25745(13) 0.54683(13) 0.13284(12) 0.0219(3) Uani 1 1 d . . . C13 C -0.24986(15) 0.42407(14) 0.11466(13) 0.0267(3) Uani 1 1 d . . . H6 H -0.1764 0.4006 0.0965 0.032 Uiso 1 1 calc R . . C14 C -0.34918(16) 0.33634(15) 0.12307(14) 0.0317(3) Uani 1 1 d . . . H7 H -0.3436 0.2530 0.1102 0.038 Uiso 1 1 calc R . . C15 C -0.45635(15) 0.36975(15) 0.15018(14) 0.0324(4) Uani 1 1 d . . . H8 H -0.5240 0.3096 0.1562 0.039 Uiso 1 1 calc R . . C16 C -0.46452(16) 0.49110(16) 0.16850(14) 0.0339(4) Uani 1 1 d . . . H9 H -0.5379 0.5142 0.1872 0.041 Uiso 1 1 calc R . . C17 C -0.36601(14) 0.57906(14) 0.15973(13) 0.0276(3) Uani 1 1 d . . . H10 H -0.3726 0.6621 0.1722 0.033 Uiso 1 1 calc R . . C18 C 0.05969(13) 0.58265(12) 0.21135(12) 0.0199(3) Uani 1 1 d . . . C19 C 0.14016(14) 0.51952(13) 0.16415(13) 0.0248(3) Uani 1 1 d . . . H11 H 0.1499 0.5281 0.0913 0.030 Uiso 1 1 calc R . . C20 C 0.20609(14) 0.44437(14) 0.22259(15) 0.0301(3) Uani 1 1 d . . . H12 H 0.2602 0.4013 0.1893 0.036 Uiso 1 1 calc R . . C21 C 0.19369(15) 0.43160(14) 0.32881(15) 0.0319(3) Uani 1 1 d . . . H13 H 0.2393 0.3802 0.3687 0.038 Uiso 1 1 calc R . . C22 C 0.11482(16) 0.49379(14) 0.37695(14) 0.0315(3) Uani 1 1 d . . . H14 H 0.1070 0.4860 0.4506 0.038 Uiso 1 1 calc R . . C23 C 0.04703(15) 0.56753(13) 0.31819(13) 0.0259(3) Uani 1 1 d . . . H15 H -0.0089 0.6084 0.3510 0.031 Uiso 1 1 calc R . . C24 C 0.50130(13) 0.79614(12) 0.43512(11) 0.0183(3) Uani 1 1 d . . . C25 C 0.52786(14) 0.69513(13) 0.47655(12) 0.0224(3) Uani 1 1 d . . . H16 H 0.5878 0.6524 0.4525 0.027 Uiso 1 1 calc R . . C26 C 0.46707(15) 0.65671(14) 0.55269(13) 0.0274(3) Uani 1 1 d . . . H17 H 0.4861 0.5882 0.5811 0.033 Uiso 1 1 calc R . . C27 C 0.37891(15) 0.71796(14) 0.58728(13) 0.0279(3) Uani 1 1 d . . . H18 H 0.3377 0.6917 0.6397 0.034 Uiso 1 1 calc R . . C28 C 0.35060(14) 0.81739(13) 0.54573(13) 0.0253(3) Uani 1 1 d . . . H19 H 0.2896 0.8591 0.5691 0.030 Uiso 1 1 calc R . . C29 C 0.41123(13) 0.85583(12) 0.47012(12) 0.0208(3) Uani 1 1 d . . . H20 H 0.3912 0.9240 0.4416 0.025 Uiso 1 1 calc R . . C30 C 0.81701(13) 0.85781(12) 0.49917(12) 0.0207(3) Uani 1 1 d . . . C31 C 0.92058(14) 0.80575(13) 0.48487(13) 0.0260(3) Uani 1 1 d . . . H21 H 0.9259 0.7799 0.4078 0.031 Uiso 1 1 calc R . . C32 C 1.01624(14) 0.79096(14) 0.58152(15) 0.0305(3) Uani 1 1 d . . . H22 H 1.0851 0.7532 0.5700 0.037 Uiso 1 1 calc R . . C33 C 1.01175(15) 0.83110(14) 0.69482(14) 0.0319(3) Uani 1 1 d . . . H23 H 1.0773 0.8211 0.7611 0.038 Uiso 1 1 calc R . . C34 C 0.91131(16) 0.88580(14) 0.71071(14) 0.0314(3) Uani 1 1 d . . . H24 H 0.9089 0.9148 0.7885 0.038 Uiso 1 1 calc R . . C35 C 0.81372(15) 0.89880(13) 0.61395(13) 0.0259(3) Uani 1 1 d . . . H25 H 0.7445 0.9357 0.6258 0.031 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0186(6) 0.0276(7) 0.0280(7) 0.0105(6) 0.0067(6) 0.0055(6) C2 0.0215(7) 0.0225(7) 0.0207(6) 0.0063(5) 0.0073(6) 0.0048(6) C3 0.0196(6) 0.0226(7) 0.0193(6) 0.0073(5) 0.0075(5) 0.0048(5) C4 0.0207(6) 0.0244(7) 0.0214(6) 0.0104(5) 0.0060(6) 0.0065(6) N1 0.0216(6) 0.0266(6) 0.0284(6) 0.0162(5) 0.0067(5) 0.0055(5) C5 0.0235(7) 0.0200(6) 0.0182(6) 0.0087(5) 0.0084(5) 0.0050(5) C6 0.0219(6) 0.0204(6) 0.0195(6) 0.0103(5) 0.0066(5) 0.0038(5) C7 0.0237(7) 0.0184(6) 0.0181(6) 0.0082(5) 0.0091(5) 0.0061(5) C8 0.0204(6) 0.0190(6) 0.0221(6) 0.0088(5) 0.0104(6) 0.0047(5) C9 0.0202(6) 0.0161(6) 0.0206(6) 0.0069(5) 0.0086(5) 0.0058(5) C10 0.0201(6) 0.0186(6) 0.0219(7) 0.0056(5) 0.0084(6) 0.0069(5) C11 0.0197(6) 0.0224(7) 0.0245(7) 0.0069(5) 0.0100(6) 0.0048(5) N2 0.0221(6) 0.0234(6) 0.0214(6) 0.0113(5) 0.0097(5) 0.0051(5) O1 0.0210(5) 0.0330(6) 0.0287(5) 0.0208(4) 0.0071(4) 0.0057(4) O2 0.0219(5) 0.0296(5) 0.0269(5) 0.0187(4) 0.0101(4) 0.0069(4) B1 0.0227(7) 0.0262(8) 0.0244(8) 0.0153(6) 0.0070(7) 0.0049(6) F1 0.0285(5) 0.0530(6) 0.0241(4) 0.0215(4) 0.0066(4) 0.0001(4) F2 0.0322(5) 0.0272(5) 0.0464(6) 0.0141(4) 0.0082(4) 0.0092(4) C12 0.0205(6) 0.0254(7) 0.0180(6) 0.0074(5) 0.0049(5) 0.0018(6) C13 0.0298(8) 0.0265(7) 0.0252(7) 0.0096(6) 0.0103(6) 0.0051(6) C14 0.0368(8) 0.0269(8) 0.0277(8) 0.0110(6) 0.0072(7) -0.0004(7) C15 0.0249(7) 0.0394(9) 0.0280(8) 0.0159(7) 0.0048(6) -0.0063(7) C16 0.0243(7) 0.0460(10) 0.0330(8) 0.0137(7) 0.0123(7) 0.0041(7) C17 0.0244(7) 0.0287(8) 0.0301(8) 0.0084(6) 0.0106(6) 0.0045(6) C18 0.0177(6) 0.0177(6) 0.0223(6) 0.0067(5) 0.0046(5) 0.0015(5) C19 0.0229(7) 0.0234(7) 0.0302(7) 0.0078(6) 0.0125(6) 0.0037(6) C20 0.0202(7) 0.0238(7) 0.0470(9) 0.0094(7) 0.0117(7) 0.0070(6) C21 0.0250(7) 0.0236(7) 0.0438(9) 0.0162(7) 0.0019(7) 0.0057(6) C22 0.0379(9) 0.0301(8) 0.0270(8) 0.0151(6) 0.0071(7) 0.0072(7) C23 0.0301(7) 0.0250(7) 0.0258(7) 0.0099(6) 0.0109(6) 0.0085(6) C24 0.0183(6) 0.0196(6) 0.0167(6) 0.0070(5) 0.0050(5) 0.0030(5) C25 0.0228(7) 0.0231(7) 0.0243(7) 0.0104(6) 0.0083(6) 0.0074(6) C26 0.0312(8) 0.0268(7) 0.0282(7) 0.0171(6) 0.0094(6) 0.0065(6) C27 0.0292(7) 0.0346(8) 0.0241(7) 0.0138(6) 0.0132(6) 0.0035(6) C28 0.0234(7) 0.0284(7) 0.0257(7) 0.0058(6) 0.0122(6) 0.0057(6) C29 0.0212(7) 0.0197(6) 0.0222(7) 0.0078(5) 0.0069(6) 0.0050(5) C30 0.0185(6) 0.0186(6) 0.0241(7) 0.0076(5) 0.0055(6) 0.0029(5) C31 0.0225(7) 0.0274(7) 0.0301(8) 0.0096(6) 0.0100(6) 0.0074(6) C32 0.0177(7) 0.0311(8) 0.0433(9) 0.0137(7) 0.0079(7) 0.0072(6) C33 0.0228(7) 0.0307(8) 0.0327(8) 0.0120(7) -0.0036(6) 0.0003(6) C34 0.0366(8) 0.0285(8) 0.0226(7) 0.0064(6) 0.0035(7) 0.0031(7) C35 0.0269(7) 0.0257(7) 0.0267(7) 0.0079(6) 0.0093(6) 0.0092(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 N1 1.3424(18) . ? C1 C2 1.384(2) . ? C1 H1 0.9500 . ? C2 C3 1.4191(19) . ? C2 C12 1.4802(19) . ? C3 C4 1.4027(19) . ? C3 C18 1.4760(19) . ? C4 N1 1.3793(18) . ? C4 C5 1.4345(19) . ? N1 H2 0.8800 . ? C5 O1 1.3230(16) . ? C5 C6 1.382(2) . ? C6 C7 1.3871(18) . ? C6 H3 0.9500 . ? C7 O2 1.3198(16) . ? C7 C8 1.430(2) . ? C8 N2 1.3777(16) . ? C8 C9 1.4030(19) . ? C9 C10 1.4148(19) . ? C9 C24 1.4797(18) . ? C10 C11 1.3864(19) . ? C10 C30 1.4790(19) . ? C11 N2 1.3432(18) . ? C11 H4 0.9500 . ? N2 H5 0.8800 . ? O1 B1 1.4754(18) . ? O2 B1 1.4679(19) . ? B1 F1 1.3804(19) . ? B1 F2 1.383(2) . ? C12 C17 1.393(2) . ? C12 C13 1.398(2) . ? C13 C14 1.388(2) . ? C13 H6 0.9500 . ? C14 C15 1.385(2) . ? C14 H7 0.9500 . ? C15 C16 1.383(2) . ? C15 H8 0.9500 . ? C16 C17 1.386(2) . ? C16 H9 0.9500 . ? C17 H10 0.9500 . ? C18 C19 1.3935(19) . ? C18 C23 1.396(2) . ? C19 C20 1.385(2) . ? C19 H11 0.9500 . ? C20 C21 1.379(2) . ? C20 H12 0.9500 . ? C21 C22 1.379(2) . ? C21 H13 0.9500 . ? C22 C23 1.384(2) . ? C22 H14 0.9500 . ? C23 H15 0.9500 . ? C24 C29 1.3932(19) . ? C24 C25 1.3949(19) . ? C25 C26 1.3883(19) . ? C25 H16 0.9500 . ? C26 C27 1.383(2) . ? C26 H17 0.9500 . ? C27 C28 1.383(2) . ? C27 H18 0.9500 . ? C28 C29 1.3815(19) . ? C28 H19 0.9500 . ? C29 H20 0.9500 . ? C30 C31 1.390(2) . ? C30 C35 1.399(2) . ? C31 C32 1.386(2) . ? C31 H21 0.9500 . ? C32 C33 1.385(2) . ? C32 H22 0.9500 . ? C33 C34 1.381(2) . ? C33 H23 0.9500 . ? C34 C35 1.389(2) . ? C34 H24 0.9500 . ? C35 H25 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 108.95(12) . . ? N1 C1 H1 125.5 . . ? C2 C1 H1 125.5 . . ? C1 C2 C3 107.24(12) . . ? C1 C2 C12 123.02(13) . . ? C3 C2 C12 129.57(13) . . ? C4 C3 C2 106.52(12) . . ? C4 C3 C18 128.61(12) . . ? C2 C3 C18 124.86(12) . . ? N1 C4 C3 107.38(12) . . ? N1 C4 C5 118.20(12) . . ? C3 C4 C5 134.32(13) . . ? C1 N1 C4 109.90(12) . . ? C1 N1 H2 125.0 . . ? C4 N1 H2 125.0 . . ? O1 C5 C6 121.26(12) . . ? O1 C5 C4 113.73(12) . . ? C6 C5 C4 124.99(12) . . ? C5 C6 C7 119.75(12) . . ? C5 C6 H3 120.1 . . ? C7 C6 H3 120.1 . . ? O2 C7 C6 120.84(12) . . ? O2 C7 C8 113.64(11) . . ? C6 C7 C8 125.49(12) . . ? N2 C8 C9 107.29(12) . . ? N2 C8 C7 118.49(12) . . ? C9 C8 C7 134.19(12) . . ? C8 C9 C10 106.84(11) . . ? C8 C9 C24 128.25(12) . . ? C10 C9 C24 124.83(12) . . ? C11 C10 C9 107.00(12) . . ? C11 C10 C30 124.08(12) . . ? C9 C10 C30 128.89(12) . . ? N2 C11 C10 109.02(12) . . ? N2 C11 H4 125.5 . . ? C10 C11 H4 125.5 . . ? C11 N2 C8 109.83(11) . . ? C11 N2 H5 125.1 . . ? C8 N2 H5 125.1 . . ? C5 O1 B1 121.51(11) . . ? C7 O2 B1 121.49(11) . . ? F1 B1 F2 109.79(12) . . ? F1 B1 O2 108.17(12) . . ? F2 B1 O2 109.96(13) . . ? F1 B1 O1 108.65(12) . . ? F2 B1 O1 108.22(12) . . ? O2 B1 O1 112.03(11) . . ? C17 C12 C13 118.77(13) . . ? C17 C12 C2 119.15(13) . . ? C13 C12 C2 121.98(13) . . ? C14 C13 C12 120.32(14) . . ? C14 C13 H6 119.8 . . ? C12 C13 H6 119.8 . . ? C15 C14 C13 120.30(15) . . ? C15 C14 H7 119.9 . . ? C13 C14 H7 119.9 . . ? C16 C15 C14 119.76(14) . . ? C16 C15 H8 120.1 . . ? C14 C15 H8 120.1 . . ? C15 C16 C17 120.25(15) . . ? C15 C16 H9 119.9 . . ? C17 C16 H9 119.9 . . ? C16 C17 C12 120.62(15) . . ? C16 C17 H10 119.7 . . ? C12 C17 H10 119.7 . . ? C19 C18 C23 118.27(13) . . ? C19 C18 C3 121.95(12) . . ? C23 C18 C3 119.66(12) . . ? C20 C19 C18 120.51(14) . . ? C20 C19 H11 119.7 . . ? C18 C19 H11 119.7 . . ? C21 C20 C19 120.44(14) . . ? C21 C20 H12 119.8 . . ? C19 C20 H12 119.8 . . ? C22 C21 C20 119.77(14) . . ? C22 C21 H13 120.1 . . ? C20 C21 H13 120.1 . . ? C21 C22 C23 120.12(14) . . ? C21 C22 H14 119.9 . . ? C23 C22 H14 119.9 . . ? C22 C23 C18 120.86(14) . . ? C22 C23 H15 119.6 . . ? C18 C23 H15 119.6 . . ? C29 C24 C25 118.67(12) . . ? C29 C24 C9 120.97(12) . . ? C25 C24 C9 120.20(12) . . ? C26 C25 C24 120.32(13) . . ? C26 C25 H16 119.8 . . ? C24 C25 H16 119.8 . . ? C27 C26 C25 120.11(13) . . ? C27 C26 H17 119.9 . . ? C25 C26 H17 119.9 . . ? C28 C27 C26 120.11(13) . . ? C28 C27 H18 119.9 . . ? C26 C27 H18 119.9 . . ? C29 C28 C27 119.83(13) . . ? C29 C28 H19 120.1 . . ? C27 C28 H19 120.1 . . ? C28 C29 C24 120.96(13) . . ? C28 C29 H20 119.5 . . ? C24 C29 H20 119.5 . . ? C31 C30 C35 118.50(13) . . ? C31 C30 C10 119.39(12) . . ? C35 C30 C10 122.09(12) . . ? C32 C31 C30 120.92(14) . . ? C32 C31 H21 119.5 . . ? C30 C31 H21 119.5 . . ? C33 C32 C31 120.17(14) . . ? C33 C32 H22 119.9 . . ? C31 C32 H22 119.9 . . ? C34 C33 C32 119.54(15) . . ? C34 C33 H23 120.2 . . ? C32 C33 H23 120.2 . . ? C33 C34 C35 120.55(15) . . ? C33 C34 H24 119.7 . . ? C35 C34 H24 119.7 . . ? C34 C35 C30 120.28(14) . . ? C34 C35 H25 119.9 . . ? C30 C35 H25 119.9 . . ? 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 N1 C1 C2 C3 0.88(16) . . . . ? N1 C1 C2 C12 -174.74(12) . . . . ? C1 C2 C3 C4 -0.36(15) . . . . ? C12 C2 C3 C4 174.88(13) . . . . ? C1 C2 C3 C18 -179.18(13) . . . . ? C12 C2 C3 C18 -3.9(2) . . . . ? C2 C3 C4 N1 -0.27(15) . . . . ? C18 C3 C4 N1 178.49(13) . . . . ? C2 C3 C4 C5 175.90(15) . . . . ? C18 C3 C4 C5 -5.3(3) . . . . ? C2 C1 N1 C4 -1.08(16) . . . . ? C3 C4 N1 C1 0.83(16) . . . . ? C5 C4 N1 C1 -176.05(12) . . . . ? N1 C4 C5 O1 -15.25(18) . . . . ? C3 C4 C5 O1 168.91(14) . . . . ? N1 C4 C5 C6 163.19(13) . . . . ? C3 C4 C5 C6 -12.7(3) . . . . ? O1 C5 C6 C7 -2.9(2) . . . . ? C4 C5 C6 C7 178.79(13) . . . . ? C5 C6 C7 O2 -1.5(2) . . . . ? C5 C6 C7 C8 -179.65(13) . . . . ? O2 C7 C8 N2 -13.11(17) . . . . ? C6 C7 C8 N2 165.14(12) . . . . ? O2 C7 C8 C9 164.41(14) . . . . ? C6 C7 C8 C9 -17.3(2) . . . . ? N2 C8 C9 C10 -0.03(14) . . . . ? C7 C8 C9 C10 -177.75(14) . . . . ? N2 C8 C9 C24 176.77(12) . . . . ? C7 C8 C9 C24 -0.9(2) . . . . ? C8 C9 C10 C11 -0.88(14) . . . . ? C24 C9 C10 C11 -177.82(12) . . . . ? C8 C9 C10 C30 177.07(13) . . . . ? C24 C9 C10 C30 0.1(2) . . . . ? C9 C10 C11 N2 1.51(15) . . . . ? C30 C10 C11 N2 -176.57(12) . . . . ? C10 C11 N2 C8 -1.57(15) . . . . ? C9 C8 N2 C11 0.99(15) . . . . ? C7 C8 N2 C11 179.12(12) . . . . ? C6 C5 O1 B1 -5.7(2) . . . . ? C4 C5 O1 B1 172.84(12) . . . . ? C6 C7 O2 B1 14.37(19) . . . . ? C8 C7 O2 B1 -167.30(12) . . . . ? C7 O2 B1 F1 -140.69(12) . . . . ? C7 O2 B1 F2 99.42(14) . . . . ? C7 O2 B1 O1 -20.96(18) . . . . ? C5 O1 B1 F1 136.00(13) . . . . ? C5 O1 B1 F2 -104.83(14) . . . . ? C5 O1 B1 O2 16.55(18) . . . . ? C1 C2 C12 C17 -40.8(2) . . . . ? C3 C2 C12 C17 144.65(15) . . . . ? C1 C2 C12 C13 135.46(15) . . . . ? C3 C2 C12 C13 -39.1(2) . . . . ? C17 C12 C13 C14 0.2(2) . . . . ? C2 C12 C13 C14 -176.08(13) . . . . ? C12 C13 C14 C15 -0.3(2) . . . . ? C13 C14 C15 C16 0.2(2) . . . . ? C14 C15 C16 C17 0.1(2) . . . . ? C15 C16 C17 C12 -0.2(2) . . . . ? C13 C12 C17 C16 0.1(2) . . . . ? C2 C12 C17 C16 176.47(13) . . . . ? C4 C3 C18 C19 -55.0(2) . . . . ? C2 C3 C18 C19 123.51(15) . . . . ? C4 C3 C18 C23 128.93(15) . . . . ? C2 C3 C18 C23 -52.52(19) . . . . ? C23 C18 C19 C20 -0.3(2) . . . . ? C3 C18 C19 C20 -176.41(13) . . . . ? C18 C19 C20 C21 -0.4(2) . . . . ? C19 C20 C21 C22 0.2(2) . . . . ? C20 C21 C22 C23 0.8(2) . . . . ? C21 C22 C23 C18 -1.6(2) . . . . ? C19 C18 C23 C22 1.3(2) . . . . ? C3 C18 C23 C22 177.50(14) . . . . ? C8 C9 C24 C29 -50.4(2) . . . . ? C10 C9 C24 C29 125.89(15) . . . . ? C8 C9 C24 C25 134.41(15) . . . . ? C10 C9 C24 C25 -49.32(19) . . . . ? C29 C24 C25 C26 -1.1(2) . . . . ? C9 C24 C25 C26 174.25(13) . . . . ? C24 C25 C26 C27 0.5(2) . . . . ? C25 C26 C27 C28 0.3(2) . . . . ? C26 C27 C28 C29 -0.4(2) . . . . ? C27 C28 C29 C24 -0.2(2) . . . . ? C25 C24 C29 C28 1.0(2) . . . . ? C9 C24 C29 C28 -174.32(13) . . . . ? C11 C10 C30 C31 -46.98(19) . . . . ? C9 C10 C30 C31 135.39(15) . . . . ? C11 C10 C30 C35 131.61(15) . . . . ? C9 C10 C30 C35 -46.0(2) . . . . ? C35 C30 C31 C32 2.1(2) . . . . ? C10 C30 C31 C32 -179.29(13) . . . . ? C30 C31 C32 C33 -1.7(2) . . . . ? C31 C32 C33 C34 0.1(2) . . . . ? C32 C33 C34 C35 1.2(2) . . . . ? C33 C34 C35 C30 -0.8(2) . . . . ? C31 C30 C35 C34 -0.9(2) . . . . ? C10 C30 C35 C34 -179.45(13) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.251 _refine_diff_density_min -0.236 _refine_diff_density_rms 0.043 # Attachment '3b.CIF' data_1227ma _database_code_depnum_ccdc_archive 'CCDC 852921' #TrackingRef '3b.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C39 H33 B F2 N2 O6' _chemical_formula_sum 'C39 H33 B F2 N2 O6' _chemical_formula_weight 674.48 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 C2/c _symmetry_space_group_name_Hall '-C 2yc' _symmetry_Int_Tables_number 15 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 14.7974(4) _cell_length_b 20.7489(5) _cell_length_c 10.5484(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.9674(15) _cell_angle_gamma 90.00 _cell_volume 3226.51(13) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.835 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.6802 _exptl_absorpt_correction_T_max 0.9212 _exptl_absorpt_process_details ? _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 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17983 _diffrn_reflns_av_R_equivalents 0.0500 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.68 _diffrn_reflns_theta_max 68.21 _reflns_number_total 2963 _reflns_number_gt 2385 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0658P)^2^+0.4389P] 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 2963 _refine_ls_number_parameters 229 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0526 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1164 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _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 O1 O 0.46653(8) 0.07657(5) 0.14087(10) 0.0407(3) Uani 1 1 d . . . F1 F 0.57002(8) -0.00152(5) 0.21416(9) 0.0500(3) Uani 1 1 d . . . O2 O 0.23831(9) 0.39364(6) -0.53957(11) 0.0507(4) Uani 1 1 d . . . C1 C 0.5000 0.17425(11) 0.2500 0.0334(5) Uani 1 2 d S . . H1 H 0.5000 0.2200 0.2500 0.040 Uiso 1 2 calc SR . . N1 N 0.41248(9) 0.12371(6) -0.07671(12) 0.0365(3) Uani 1 1 d . . . H2 H 0.4204 0.0817 -0.0711 0.044 Uiso 1 1 calc R . . O3 O 0.40739(10) 0.48200(6) 0.16521(13) 0.0587(4) Uani 1 1 d . . . C2 C 0.46640(11) 0.14076(7) 0.14232(14) 0.0339(4) Uani 1 1 d . . . C3 C 0.28311(11) 0.31856(8) -0.22270(15) 0.0374(4) Uani 1 1 d . . . H3 H 0.2681 0.3238 -0.1376 0.045 Uiso 1 1 calc R . . C4 C 0.37653(11) 0.22021(8) -0.15641(15) 0.0351(4) Uani 1 1 d . . . C5 C 0.42999(11) 0.16676(8) 0.02254(14) 0.0335(4) Uani 1 1 d . . . C6 C 0.45558(12) 0.34328(8) -0.02300(15) 0.0398(4) Uani 1 1 d . . . H4 H 0.4855 0.3348 -0.0973 0.048 Uiso 1 1 calc R . . C7 C 0.38167(11) 0.15519(8) -0.18252(15) 0.0373(4) Uani 1 1 d . . . H5 H 0.3658 0.1358 -0.2630 0.045 Uiso 1 1 calc R . . C8 C 0.40763(11) 0.22869(8) -0.02624(14) 0.0332(4) Uani 1 1 d . . . C9 C 0.24722(12) 0.36099(8) -0.31561(15) 0.0391(4) Uani 1 1 d . . . H6 H 0.2077 0.3946 -0.2941 0.047 Uiso 1 1 calc R . . C10 C 0.34073(11) 0.26847(8) -0.25155(15) 0.0361(4) Uani 1 1 d . . . C11 C 0.37146(12) 0.30637(8) 0.14584(15) 0.0375(4) Uani 1 1 d . . . H7 H 0.3440 0.2725 0.1894 0.045 Uiso 1 1 calc R . . C12 C 0.36108(12) 0.26235(9) -0.37773(15) 0.0420(4) Uani 1 1 d . . . H8 H 0.3998 0.2284 -0.4001 0.050 Uiso 1 1 calc R . . C13 C 0.40909(13) 0.41823(8) 0.12999(17) 0.0455(5) Uani 1 1 d . . . C14 C 0.45439(13) 0.40490(8) 0.02336(17) 0.0453(5) Uani 1 1 d . . . H9 H 0.4845 0.4384 -0.0175 0.054 Uiso 1 1 calc R . . C15 C 0.36849(12) 0.36898(8) 0.19301(16) 0.0423(4) Uani 1 1 d . . . H10 H 0.3389 0.3778 0.2676 0.051 Uiso 1 1 calc R . . C16 C 0.41360(11) 0.29243(8) 0.03678(14) 0.0343(4) Uani 1 1 d . . . C17 C 0.26943(12) 0.35413(8) -0.44014(15) 0.0414(4) Uani 1 1 d . . . C21 C 0.18598(15) 0.44836(10) -0.50919(17) 0.0585(6) Uani 1 1 d . . . H11 H 0.1302 0.4339 -0.4742 0.088 Uiso 1 1 calc R . . H12 H 0.1705 0.4737 -0.5864 0.088 Uiso 1 1 calc R . . H13 H 0.2213 0.4750 -0.4461 0.088 Uiso 1 1 calc R . . C19 C 0.32637(13) 0.30440(9) -0.47054(16) 0.0450(5) Uani 1 1 d . . . H14 H 0.3415 0.2993 -0.5557 0.054 Uiso 1 1 calc R . . C20 C 0.36191(17) 0.49658(10) 0.2756(2) 0.0680(7) Uani 1 1 d . . . H15 H 0.2976 0.4853 0.2602 0.102 Uiso 1 1 calc R . . H16 H 0.3676 0.5427 0.2944 0.102 Uiso 1 1 calc R . . H17 H 0.3893 0.4718 0.3481 0.102 Uiso 1 1 calc R . . B1 B 0.5000 0.03707(13) 0.2500 0.0378(6) Uani 1 2 d S . . 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 O1 0.0679(8) 0.0239(6) 0.0283(6) -0.0007(4) -0.0066(5) -0.0003(5) F1 0.0745(8) 0.0414(6) 0.0328(5) -0.0034(4) -0.0038(5) 0.0154(5) O2 0.0712(9) 0.0444(8) 0.0340(6) 0.0027(5) -0.0101(6) 0.0179(6) C1 0.0451(13) 0.0231(12) 0.0310(11) 0.000 -0.0022(9) 0.000 N1 0.0525(8) 0.0261(7) 0.0295(7) -0.0014(6) -0.0044(6) 0.0006(6) O3 0.0784(10) 0.0295(7) 0.0632(9) -0.0067(6) -0.0223(7) 0.0021(6) C2 0.0456(9) 0.0253(9) 0.0304(8) 0.0017(6) 0.0009(7) 0.0003(7) C3 0.0447(9) 0.0363(10) 0.0298(8) -0.0019(7) -0.0050(7) -0.0025(7) C4 0.0424(9) 0.0333(9) 0.0287(8) 0.0005(7) -0.0021(6) -0.0008(7) C5 0.0428(9) 0.0282(9) 0.0285(8) -0.0018(7) -0.0017(6) -0.0017(7) C6 0.0484(10) 0.0361(10) 0.0329(9) 0.0066(7) -0.0095(7) -0.0050(8) C7 0.0491(10) 0.0360(10) 0.0255(8) -0.0014(7) -0.0046(7) 0.0015(7) C8 0.0389(9) 0.0309(9) 0.0289(8) 0.0018(6) -0.0031(6) -0.0018(7) C9 0.0442(10) 0.0333(9) 0.0378(9) -0.0033(7) -0.0072(7) 0.0024(7) C10 0.0419(9) 0.0335(10) 0.0312(9) 0.0008(7) -0.0061(7) -0.0014(7) C11 0.0479(10) 0.0288(9) 0.0339(8) 0.0010(7) -0.0065(7) 0.0004(7) C12 0.0496(10) 0.0419(11) 0.0336(9) 0.0016(7) -0.0011(7) 0.0077(8) C13 0.0572(11) 0.0246(9) 0.0498(11) 0.0001(8) -0.0231(8) -0.0006(8) C14 0.0570(11) 0.0328(10) 0.0427(10) 0.0083(8) -0.0154(8) -0.0082(8) C15 0.0527(11) 0.0359(10) 0.0359(9) -0.0040(7) -0.0104(7) 0.0051(8) C16 0.0435(9) 0.0285(9) 0.0288(8) 0.0014(6) -0.0093(7) -0.0010(7) C17 0.0507(10) 0.0398(10) 0.0315(9) 0.0027(7) -0.0097(7) 0.0035(8) C21 0.0796(14) 0.0515(12) 0.0409(10) -0.0011(9) -0.0147(9) 0.0264(10) C19 0.0563(11) 0.0473(11) 0.0303(9) 0.0011(8) -0.0019(8) 0.0091(9) C20 0.0952(17) 0.0403(12) 0.0622(14) -0.0150(10) -0.0292(12) 0.0193(11) B1 0.0600(17) 0.0248(14) 0.0276(12) 0.000 -0.0019(12) 0.000 _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 O1 C2 1.3321(18) . ? O1 B1 1.4640(18) . ? F1 B1 1.3876(18) . ? O2 C17 1.3786(19) . ? O2 C21 1.426(2) . ? C1 C2 1.3865(18) . ? C1 C2 1.3865(18) 2_655 ? C1 H1 0.9500 . ? N1 C7 1.3386(19) . ? N1 C5 1.3835(18) . ? N1 H2 0.8800 . ? O3 C13 1.375(2) . ? O3 C20 1.427(3) . ? C2 C5 1.435(2) . ? C3 C9 1.388(2) . ? C3 C10 1.395(2) . ? C3 H3 0.9500 . ? C4 C7 1.380(2) . ? C4 C8 1.421(2) . ? C4 C10 1.483(2) . ? C5 C8 1.413(2) . ? C6 C14 1.370(2) . ? C6 C16 1.402(2) . ? C6 H4 0.9500 . ? C7 H5 0.9500 . ? C8 C16 1.479(2) . ? C9 C17 1.389(2) . ? C9 H6 0.9500 . ? C10 C12 1.396(2) . ? C11 C16 1.386(2) . ? C11 C15 1.393(2) . ? C11 H7 0.9500 . ? C12 C19 1.377(2) . ? C12 H8 0.9500 . ? C13 C15 1.384(2) . ? C13 C14 1.386(3) . ? C14 H9 0.9500 . ? C15 H10 0.9500 . ? C17 C19 1.387(2) . ? C21 H11 0.9800 . ? C21 H12 0.9800 . ? C21 H13 0.9800 . ? C19 H14 0.9500 . ? C20 H15 0.9800 . ? C20 H16 0.9800 . ? C20 H17 0.9800 . ? B1 F1 1.3876(18) 2_655 ? B1 O1 1.4640(18) 2_655 ? 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 O1 B1 123.47(13) . . ? C17 O2 C21 117.03(13) . . ? C2 C1 C2 119.8(2) . 2_655 ? C2 C1 H1 120.1 . . ? C2 C1 H1 120.1 2_655 . ? C7 N1 C5 110.12(13) . . ? C7 N1 H2 124.9 . . ? C5 N1 H2 124.9 . . ? C13 O3 C20 116.45(16) . . ? O1 C2 C1 120.65(15) . . ? O1 C2 C5 111.50(13) . . ? C1 C2 C5 127.84(15) . . ? C9 C3 C10 121.49(15) . . ? C9 C3 H3 119.3 . . ? C10 C3 H3 119.3 . . ? C7 C4 C8 107.16(14) . . ? C7 C4 C10 123.20(14) . . ? C8 C4 C10 129.59(15) . . ? N1 C5 C8 106.80(13) . . ? N1 C5 C2 117.06(14) . . ? C8 C5 C2 136.11(14) . . ? C14 C6 C16 121.48(17) . . ? C14 C6 H4 119.3 . . ? C16 C6 H4 119.3 . . ? N1 C7 C4 109.33(14) . . ? N1 C7 H5 125.3 . . ? C4 C7 H5 125.3 . . ? C5 C8 C4 106.58(14) . . ? C5 C8 C16 130.28(14) . . ? C4 C8 C16 123.14(14) . . ? C3 C9 C17 119.69(16) . . ? C3 C9 H6 120.2 . . ? C17 C9 H6 120.2 . . ? C3 C10 C12 117.54(15) . . ? C3 C10 C4 123.02(14) . . ? C12 C10 C4 119.35(15) . . ? C16 C11 C15 121.43(16) . . ? C16 C11 H7 119.3 . . ? C15 C11 H7 119.3 . . ? C19 C12 C10 121.50(16) . . ? C19 C12 H8 119.3 . . ? C10 C12 H8 119.3 . . ? O3 C13 C15 124.17(18) . . ? O3 C13 C14 115.64(17) . . ? C15 C13 C14 120.19(16) . . ? C6 C14 C13 119.88(17) . . ? C6 C14 H9 120.1 . . ? C13 C14 H9 120.1 . . ? C13 C15 C11 119.23(17) . . ? C13 C15 H10 120.4 . . ? C11 C15 H10 120.4 . . ? C11 C16 C6 117.73(15) . . ? C11 C16 C8 123.09(15) . . ? C6 C16 C8 118.83(15) . . ? O2 C17 C19 115.85(15) . . ? O2 C17 C9 124.60(16) . . ? C19 C17 C9 119.55(15) . . ? O2 C21 H11 109.5 . . ? O2 C21 H12 109.5 . . ? H11 C21 H12 109.5 . . ? O2 C21 H13 109.5 . . ? H11 C21 H13 109.5 . . ? H12 C21 H13 109.5 . . ? C12 C19 C17 120.23(16) . . ? C12 C19 H14 119.9 . . ? C17 C19 H14 119.9 . . ? O3 C20 H15 109.5 . . ? O3 C20 H16 109.5 . . ? H15 C20 H16 109.5 . . ? O3 C20 H17 109.5 . . ? H15 C20 H17 109.5 . . ? H16 C20 H17 109.5 . . ? F1 B1 F1 109.5(2) 2_655 . ? F1 B1 O1 108.57(6) 2_655 2_655 ? F1 B1 O1 109.12(6) . 2_655 ? F1 B1 O1 109.12(6) 2_655 . ? F1 B1 O1 108.57(6) . . ? O1 B1 O1 111.91(19) 2_655 . ? 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 C2 C1 0.8(2) . . . . ? B1 O1 C2 C5 179.90(11) . . . . ? C2 C1 C2 O1 -0.40(10) 2_655 . . . ? C2 C1 C2 C5 -179.32(19) 2_655 . . . ? C7 N1 C5 C8 0.43(18) . . . . ? C7 N1 C5 C2 -178.05(14) . . . . ? O1 C2 C5 N1 -7.9(2) . . . . ? C1 C2 C5 N1 171.10(14) . . . . ? O1 C2 C5 C8 174.19(18) . . . . ? C1 C2 C5 C8 -6.8(3) . . . . ? C5 N1 C7 C4 -0.83(19) . . . . ? C8 C4 C7 N1 0.88(19) . . . . ? C10 C4 C7 N1 -176.97(15) . . . . ? N1 C5 C8 C4 0.11(18) . . . . ? C2 C5 C8 C4 178.17(18) . . . . ? N1 C5 C8 C16 -179.37(16) . . . . ? C2 C5 C8 C16 -1.3(3) . . . . ? C7 C4 C8 C5 -0.60(18) . . . . ? C10 C4 C8 C5 177.06(16) . . . . ? C7 C4 C8 C16 178.94(15) . . . . ? C10 C4 C8 C16 -3.4(3) . . . . ? C10 C3 C9 C17 -0.6(3) . . . . ? C9 C3 C10 C12 -0.1(2) . . . . ? C9 C3 C10 C4 -176.73(15) . . . . ? C7 C4 C10 C3 137.69(18) . . . . ? C8 C4 C10 C3 -39.6(3) . . . . ? C7 C4 C10 C12 -38.9(2) . . . . ? C8 C4 C10 C12 143.79(18) . . . . ? C3 C10 C12 C19 0.5(3) . . . . ? C4 C10 C12 C19 177.29(16) . . . . ? C20 O3 C13 C15 1.3(2) . . . . ? C20 O3 C13 C14 -179.34(15) . . . . ? C16 C6 C14 C13 -1.5(2) . . . . ? O3 C13 C14 C6 -176.54(15) . . . . ? C15 C13 C14 C6 2.9(3) . . . . ? O3 C13 C15 C11 177.47(15) . . . . ? C14 C13 C15 C11 -1.9(2) . . . . ? C16 C11 C15 C13 -0.5(2) . . . . ? C15 C11 C16 C6 1.7(2) . . . . ? C15 C11 C16 C8 -171.42(15) . . . . ? C14 C6 C16 C11 -0.7(2) . . . . ? C14 C6 C16 C8 172.72(15) . . . . ? C5 C8 C16 C11 -56.0(2) . . . . ? C4 C8 C16 C11 124.60(18) . . . . ? C5 C8 C16 C6 130.92(18) . . . . ? C4 C8 C16 C6 -48.5(2) . . . . ? C21 O2 C17 C19 -174.82(17) . . . . ? C21 O2 C17 C9 5.6(3) . . . . ? C3 C9 C17 O2 -179.56(16) . . . . ? C3 C9 C17 C19 0.8(3) . . . . ? C10 C12 C19 C17 -0.3(3) . . . . ? O2 C17 C19 C12 179.95(16) . . . . ? C9 C17 C19 C12 -0.4(3) . . . . ? C2 O1 B1 F1 119.77(17) . . . 2_655 ? C2 O1 B1 F1 -120.92(17) . . . . ? C2 O1 B1 O1 -0.41(10) . . . 2_655 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 68.21 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.180 _refine_diff_density_min -0.243 _refine_diff_density_rms 0.047 data_90609mae _database_code_depnum_ccdc_archive 'CCDC 852922' #TrackingRef '4b_rev.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H17 B F2 N2 O6' _chemical_formula_weight 370.12 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.030(5) _cell_length_b 9.349(5) _cell_length_c 11.595(5) _cell_angle_alpha 85.300(19) _cell_angle_beta 72.98(2) _cell_angle_gamma 81.74(2) _cell_volume 823.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 384 _exptl_absorpt_coefficient_mu 0.128 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9626 _exptl_absorpt_correction_T_max 0.9810 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\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 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8212 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0377 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.25 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3754 _reflns_number_gt 2995 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0503P)^2^+0.1423P] 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 3754 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0501 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.1002 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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 F1 F 0.37943(10) 0.69296(9) 0.60246(8) 0.0265(2) Uani 1 1 d . . . F2 F 0.56111(11) 0.76641(9) 0.42562(7) 0.0274(2) Uani 1 1 d . . . O1 O 0.58771(12) 0.84154(10) 0.60400(8) 0.0203(2) Uani 1 1 d . . . O2 O 0.67300(13) 0.59098(10) 0.54451(8) 0.0217(2) Uani 1 1 d . . . O3 O 0.97051(12) 0.42673(11) 0.80444(8) 0.0224(2) Uani 1 1 d . . . O4 O 0.70267(14) 1.12719(11) 1.00096(9) 0.0281(2) Uani 1 1 d . . . O5 O 1.09938(13) 0.12558(10) 0.73533(9) 0.0250(2) Uani 1 1 d . . . N2 N 0.57132(15) 1.06384(12) 0.74436(10) 0.0208(2) Uani 1 1 d . . . H1 H 0.5200 1.0877 0.6869 0.025 Uiso 1 1 calc R . . N1 N 0.84143(15) 0.32191(12) 0.55967(10) 0.0219(3) Uani 1 1 d . . . H2 H 0.7872 0.3347 0.5030 0.026 Uiso 1 1 calc R . . O6 O 0.79293(14) 0.81725(11) 0.91200(9) 0.0264(2) Uani 1 1 d . . . C11 C 0.65289(17) 0.92856(14) 0.76455(12) 0.0189(3) Uani 1 1 d . . . C12 C 0.66017(16) 0.81092(14) 0.69344(11) 0.0176(3) Uani 1 1 d . . . C13 C 0.73993(17) 0.67228(14) 0.71139(12) 0.0199(3) Uani 1 1 d . . . H3 H 0.7880 0.6503 0.7774 0.024 Uiso 1 1 calc R . . C14 C 0.74882(17) 0.56654(14) 0.63230(11) 0.0184(3) Uani 1 1 d . . . C15 C 0.58174(18) 1.15476(15) 0.82605(13) 0.0235(3) Uani 1 1 d . . . H4 H 0.5370 1.2545 0.8297 0.028 Uiso 1 1 calc R . . C16 C 1.00120(17) 0.21873(15) 0.67797(12) 0.0202(3) Uani 1 1 d . . . C17 C 0.71397(17) 0.93597(15) 0.86538(12) 0.0200(3) Uani 1 1 d . . . C18 C 0.84145(17) 0.42522(14) 0.63721(11) 0.0188(3) Uani 1 1 d . . . C19 C 0.66814(17) 1.07889(15) 0.90339(12) 0.0213(3) Uani 1 1 d . . . B1 B 0.5495(2) 0.72276(17) 0.54384(14) 0.0205(3) Uani 1 1 d . . . C22 C 0.93731(18) 0.19709(15) 0.58316(13) 0.0226(3) Uani 1 1 d . . . H5 H 0.9571 0.1100 0.5416 0.027 Uiso 1 1 calc R . . C23 C 0.94218(17) 0.36206(14) 0.71185(12) 0.0187(3) Uani 1 1 d . . . C24 C 0.6423(2) 1.27670(16) 1.02305(14) 0.0306(3) Uani 1 1 d . . . H6 H 0.7049 1.3364 0.9552 0.046 Uiso 1 1 calc R . . H7 H 0.6645 1.3011 1.0974 0.046 Uiso 1 1 calc R . . H8 H 0.5160 1.2951 1.0318 0.046 Uiso 1 1 calc R . . C25 C 0.8931(2) 0.83857(18) 0.99056(16) 0.0364(4) Uani 1 1 d . . . H9 H 0.9796 0.9041 0.9506 0.055 Uiso 1 1 calc R . . H10 H 0.9538 0.7454 1.0104 0.055 Uiso 1 1 calc R . . H11 H 0.8148 0.8809 1.0648 0.055 Uiso 1 1 calc R . . C26 C 1.15873(19) -0.01233(15) 0.68246(14) 0.0260(3) Uani 1 1 d . . . H12 H 1.0572 -0.0602 0.6839 0.039 Uiso 1 1 calc R . . H13 H 1.2296 -0.0723 0.7285 0.039 Uiso 1 1 calc R . . H14 H 1.2300 0.0010 0.5988 0.039 Uiso 1 1 calc R . . C27 C 1.1437(2) 0.4622(2) 0.78022(17) 0.0491(5) Uani 1 1 d . . . H15 H 1.2279 0.3755 0.7564 0.074 Uiso 1 1 calc R . . H16 H 1.1582 0.4992 0.8529 0.074 Uiso 1 1 calc R . . H17 H 1.1645 0.5364 0.7146 0.074 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 F1 0.0227(4) 0.0263(4) 0.0330(5) -0.0044(4) -0.0110(3) -0.0028(3) F2 0.0376(5) 0.0258(4) 0.0211(4) -0.0009(3) -0.0155(4) 0.0040(4) O1 0.0234(5) 0.0190(5) 0.0217(5) -0.0001(4) -0.0132(4) 0.0006(4) O2 0.0262(5) 0.0204(5) 0.0215(5) -0.0031(4) -0.0136(4) 0.0029(4) O3 0.0234(5) 0.0251(5) 0.0216(5) -0.0049(4) -0.0114(4) 0.0000(4) O4 0.0300(5) 0.0295(6) 0.0292(5) -0.0112(4) -0.0135(4) -0.0015(4) O5 0.0283(5) 0.0209(5) 0.0282(5) -0.0023(4) -0.0155(4) 0.0057(4) N2 0.0238(6) 0.0176(5) 0.0237(6) -0.0001(4) -0.0119(5) -0.0008(4) N1 0.0242(6) 0.0217(6) 0.0232(6) -0.0035(5) -0.0136(5) 0.0017(5) O6 0.0343(6) 0.0217(5) 0.0307(5) -0.0023(4) -0.0229(4) 0.0012(4) C11 0.0172(6) 0.0186(6) 0.0219(6) 0.0003(5) -0.0080(5) -0.0013(5) C12 0.0141(6) 0.0226(7) 0.0164(6) 0.0000(5) -0.0049(5) -0.0026(5) C13 0.0205(6) 0.0212(7) 0.0197(6) 0.0001(5) -0.0099(5) 0.0000(5) C14 0.0172(6) 0.0219(7) 0.0175(6) 0.0011(5) -0.0076(5) -0.0026(5) C15 0.0236(7) 0.0193(7) 0.0281(7) -0.0028(6) -0.0078(6) -0.0023(5) C16 0.0190(6) 0.0205(7) 0.0211(6) -0.0011(5) -0.0073(5) 0.0010(5) C17 0.0175(6) 0.0226(7) 0.0209(6) -0.0010(5) -0.0072(5) -0.0022(5) C18 0.0201(6) 0.0189(6) 0.0178(6) -0.0028(5) -0.0060(5) -0.0009(5) C19 0.0185(6) 0.0249(7) 0.0221(6) -0.0050(5) -0.0059(5) -0.0049(5) B1 0.0223(7) 0.0211(7) 0.0205(7) -0.0015(6) -0.0111(6) 0.0008(6) C22 0.0240(7) 0.0202(7) 0.0248(7) -0.0047(5) -0.0106(6) 0.0028(5) C23 0.0186(6) 0.0198(6) 0.0189(6) -0.0021(5) -0.0075(5) -0.0006(5) C24 0.0320(8) 0.0281(8) 0.0316(8) -0.0111(6) -0.0045(6) -0.0079(6) C25 0.0454(9) 0.0335(8) 0.0437(9) -0.0017(7) -0.0347(8) -0.0018(7) C26 0.0254(7) 0.0193(7) 0.0326(8) -0.0032(6) -0.0100(6) 0.0041(5) C27 0.0397(10) 0.0754(14) 0.0403(10) -0.0172(10) -0.0093(8) -0.0297(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 B1 1.3923(19) . ? F2 B1 1.3778(18) . ? O1 C12 1.3238(17) . ? O1 B1 1.4713(19) . ? O2 C14 1.3205(17) . ? O2 B1 1.4676(18) . ? O3 C23 1.3633(17) . ? O3 C27 1.418(2) . ? O4 C19 1.3653(17) . ? O4 C24 1.4302(19) . ? O5 C16 1.3554(17) . ? O5 C26 1.4308(17) . ? N2 C15 1.3511(19) . ? N2 C11 1.3735(18) . ? N2 H1 0.8800 . ? N1 C22 1.3569(18) . ? N1 C18 1.3724(18) . ? N1 H2 0.8800 . ? O6 C17 1.3514(17) . ? O6 C25 1.4215(19) . ? C11 C17 1.4039(19) . ? C11 C12 1.4124(19) . ? C12 C13 1.3888(19) . ? C13 C14 1.3833(19) . ? C13 H3 0.9500 . ? C14 C18 1.4255(19) . ? C15 C19 1.381(2) . ? C15 H4 0.9500 . ? C16 C22 1.382(2) . ? C16 C23 1.4032(19) . ? C17 C19 1.405(2) . ? C18 C23 1.3931(19) . ? C22 H5 0.9500 . ? C24 H6 0.9800 . ? C24 H7 0.9800 . ? C24 H8 0.9800 . ? C25 H9 0.9800 . ? C25 H10 0.9800 . ? C25 H11 0.9800 . ? C26 H12 0.9800 . ? C26 H13 0.9800 . ? C26 H14 0.9800 . ? C27 H15 0.9800 . ? C27 H16 0.9800 . ? C27 H17 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 C12 O1 B1 119.34(11) . . ? C14 O2 B1 119.26(11) . . ? C23 O3 C27 113.81(11) . . ? C19 O4 C24 114.51(12) . . ? C16 O5 C26 114.69(11) . . ? C15 N2 C11 109.78(12) . . ? C15 N2 H1 125.1 . . ? C11 N2 H1 125.1 . . ? C22 N1 C18 110.00(12) . . ? C22 N1 H2 125.0 . . ? C18 N1 H2 125.0 . . ? C17 O6 C25 117.71(12) . . ? N2 C11 C17 106.97(12) . . ? N2 C11 C12 122.15(12) . . ? C17 C11 C12 130.85(13) . . ? O1 C12 C13 120.74(12) . . ? O1 C12 C11 115.24(12) . . ? C13 C12 C11 124.00(13) . . ? C14 C13 C12 119.46(13) . . ? C14 C13 H3 120.3 . . ? C12 C13 H3 120.3 . . ? O2 C14 C13 121.72(12) . . ? O2 C14 C18 114.93(12) . . ? C13 C14 C18 123.34(12) . . ? N2 C15 C19 108.84(12) . . ? N2 C15 H4 125.6 . . ? C19 C15 H4 125.6 . . ? O5 C16 C22 130.02(12) . . ? O5 C16 C23 122.61(12) . . ? C22 C16 C23 107.36(12) . . ? O6 C17 C11 121.30(12) . . ? O6 C17 C19 131.36(13) . . ? C11 C17 C19 107.27(12) . . ? N1 C18 C23 106.97(12) . . ? N1 C18 C14 121.37(12) . . ? C23 C18 C14 131.66(13) . . ? O4 C19 C15 128.48(13) . . ? O4 C19 C17 124.37(13) . . ? C15 C19 C17 107.13(12) . . ? F2 B1 F1 109.38(12) . . ? F2 B1 O2 108.40(11) . . ? F1 B1 O2 109.40(12) . . ? F2 B1 O1 108.61(12) . . ? F1 B1 O1 108.68(11) . . ? O2 B1 O1 112.33(12) . . ? N1 C22 C16 108.11(12) . . ? N1 C22 H5 125.9 . . ? C16 C22 H5 125.9 . . ? O3 C23 C18 125.75(12) . . ? O3 C23 C16 126.62(12) . . ? C18 C23 C16 107.56(12) . . ? O4 C24 H6 109.5 . . ? O4 C24 H7 109.5 . . ? H6 C24 H7 109.5 . . ? O4 C24 H8 109.5 . . ? H6 C24 H8 109.5 . . ? H7 C24 H8 109.5 . . ? O6 C25 H9 109.5 . . ? O6 C25 H10 109.5 . . ? H9 C25 H10 109.5 . . ? O6 C25 H11 109.5 . . ? H9 C25 H11 109.5 . . ? H10 C25 H11 109.5 . . ? O5 C26 H12 109.5 . . ? O5 C26 H13 109.5 . . ? H12 C26 H13 109.5 . . ? O5 C26 H14 109.5 . . ? H12 C26 H14 109.5 . . ? H13 C26 H14 109.5 . . ? O3 C27 H15 109.5 . . ? O3 C27 H16 109.5 . . ? H15 C27 H16 109.5 . . ? O3 C27 H17 109.5 . . ? H15 C27 H17 109.5 . . ? H16 C27 H17 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 C15 N2 C11 C17 1.10(15) . . . . ? C15 N2 C11 C12 179.15(12) . . . . ? B1 O1 C12 C13 16.24(18) . . . . ? B1 O1 C12 C11 -165.15(11) . . . . ? N2 C11 C12 O1 1.99(18) . . . . ? C17 C11 C12 O1 179.52(13) . . . . ? N2 C11 C12 C13 -179.45(12) . . . . ? C17 C11 C12 C13 -1.9(2) . . . . ? O1 C12 C13 C14 2.22(19) . . . . ? C11 C12 C13 C14 -176.26(12) . . . . ? B1 O2 C14 C13 -11.64(19) . . . . ? B1 O2 C14 C18 169.37(12) . . . . ? C12 C13 C14 O2 -4.6(2) . . . . ? C12 C13 C14 C18 174.26(12) . . . . ? C11 N2 C15 C19 -1.21(16) . . . . ? C26 O5 C16 C22 6.3(2) . . . . ? C26 O5 C16 C23 -175.40(12) . . . . ? C25 O6 C17 C11 162.95(14) . . . . ? C25 O6 C17 C19 -20.7(2) . . . . ? N2 C11 C17 O6 176.58(12) . . . . ? C12 C11 C17 O6 -1.2(2) . . . . ? N2 C11 C17 C19 -0.57(15) . . . . ? C12 C11 C17 C19 -178.38(13) . . . . ? C22 N1 C18 C23 0.21(15) . . . . ? C22 N1 C18 C14 -179.51(12) . . . . ? O2 C14 C18 N1 -3.46(19) . . . . ? C13 C14 C18 N1 177.57(12) . . . . ? O2 C14 C18 C23 176.90(13) . . . . ? C13 C14 C18 C23 -2.1(2) . . . . ? C24 O4 C19 C15 -0.9(2) . . . . ? C24 O4 C19 C17 -179.44(13) . . . . ? N2 C15 C19 O4 -177.88(13) . . . . ? N2 C15 C19 C17 0.82(16) . . . . ? O6 C17 C19 O4 1.9(2) . . . . ? C11 C17 C19 O4 178.63(12) . . . . ? O6 C17 C19 C15 -176.89(14) . . . . ? C11 C17 C19 C15 -0.14(15) . . . . ? C14 O2 B1 F2 147.84(12) . . . . ? C14 O2 B1 F1 -92.96(15) . . . . ? C14 O2 B1 O1 27.82(17) . . . . ? C12 O1 B1 F2 -150.11(11) . . . . ? C12 O1 B1 F1 90.97(14) . . . . ? C12 O1 B1 O2 -30.22(17) . . . . ? C18 N1 C22 C16 0.10(16) . . . . ? O5 C16 C22 N1 178.17(13) . . . . ? C23 C16 C22 N1 -0.37(16) . . . . ? C27 O3 C23 C18 -108.42(17) . . . . ? C27 O3 C23 C16 74.91(19) . . . . ? N1 C18 C23 O3 -177.63(12) . . . . ? C14 C18 C23 O3 2.0(2) . . . . ? N1 C18 C23 C16 -0.44(15) . . . . ? C14 C18 C23 C16 179.25(14) . . . . ? O5 C16 C23 O3 -1.0(2) . . . . ? C22 C16 C23 O3 177.67(13) . . . . ? O5 C16 C23 C18 -178.18(12) . . . . ? C22 C16 C23 C18 0.50(15) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.321 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.047