# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is © The Royal Society of Chemistry and Owner Societies 2010 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_Cambridge 0171 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Noel Boens' _publ_contact_author_email noel.boens@chem.kuleuven.be _publ_section_title ; Generalized solvent scales as a tool for investigating solvent dependence of spectroscopic and kinetic parameters. Application to fluorescent BODIPY dyes ; loop_ _publ_author_name 'Noel Boens' 'M.Van der Auweraer' 'W.De Borggraeve' 'Javier Catalan' 'Lesley Pandey' ; A.Filarowski ; 'Gosia Kluba' # Attachment '- olo3dc.cif' data_olo3dc _database_code_depnum_ccdc_archive 'CCDC 711447' #TrackingRef '- olo3dc.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-[4-(methoxycarbonyl)phenyl] -1,3,5,7-tetramethyl-4,4-difluoro-3a, 4a-diaza-4-bora-s-indacene ; _chemical_name_common ; 8-(4-(methoxycarbonyl)phenyl) -1,3,5,7-tetramethyl-4,4- difluoro-3a, 4a-diaza-4-bora-s-indacene ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H21 B F2 N2 O2' _chemical_formula_weight 382.21 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 'C 2 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 32.787(6) _cell_length_b 7.992(5) _cell_length_c 7.252(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.19(4) _cell_angle_gamma 90.00 _cell_volume 1900.3(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2350 _cell_measurement_theta_min 2.81 _cell_measurement_theta_max 25.06 _exptl_crystal_description plate _exptl_crystal_colour 'darkly in red brown' _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.895 _exptl_absorpt_correction_T_max 0.911 _exptl_absorpt_process_details 'CrysAlis Red.1.171.30, Oxford Diffraction ' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'KM4 CCD' _diffrn_measurement_method /w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10097 _diffrn_reflns_av_R_equivalents 0.0386 _diffrn_reflns_av_sigmaI/netI 0.0364 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 38 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 25.06 _reflns_number_total 2889 _reflns_number_gt 2482 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'KM4CCD Software, (Oxford Diffraction Poland Sp, 1995-2003' _computing_cell_refinement 'KM4CCD Software, (Oxford Diffraction Poland Sp, 1995-2003' _computing_data_reduction 'KM4CCD Software, (Oxford Diffraction Poland Sp, 1995-2003' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP III (Farrugia, 1997 )' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0443P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(6) _refine_ls_number_reflns 2889 _refine_ls_number_parameters 258 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0677 _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_restrained_S_all 1.006 _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 -0.69029(4) 0.38266(15) -0.87399(15) 0.0281(3) Uani 1 1 d . . . F2 F -0.72714(3) 0.58752(15) -0.73567(14) 0.0242(3) Uani 1 1 d . . . O1 O -0.53937(5) 1.51279(19) -1.1805(2) 0.0312(4) Uani 1 1 d . . . O2 O -0.49399(4) 1.31173(19) -1.2489(2) 0.0310(4) Uani 1 1 d . . . N1 N -0.65383(5) 0.6159(2) -0.7412(2) 0.0198(4) Uani 1 1 d . . . N2 N -0.69500(5) 0.6499(2) -1.0263(2) 0.0196(4) Uani 1 1 d . . . C1 C -0.64014(6) 0.5608(3) -0.5753(3) 0.0238(5) Uani 1 1 d . . . C2 C -0.60645(6) 0.6566(3) -0.5240(3) 0.0239(5) Uani 1 1 d . . . H2 H -0.5913 0.6435 -0.4131 0.029 Uiso 1 1 calc R . . C3 C -0.59865(6) 0.7734(3) -0.6595(3) 0.0231(5) Uani 1 1 d . . . C4 C -0.62885(6) 0.7475(3) -0.7986(3) 0.0198(4) Uani 1 1 d . . . C5 C -0.63665(6) 0.8280(3) -0.9677(2) 0.0185(4) Uani 1 1 d . . . C6 C -0.66905(6) 0.7804(2) -1.0800(3) 0.0189(4) Uani 1 1 d . . . C7 C -0.68331(6) 0.8408(3) -1.2552(3) 0.0210(4) Uani 1 1 d . . . C8 C -0.71674(6) 0.7456(3) -1.2996(3) 0.0220(4) Uani 1 1 d . . . H8 H -0.7326 0.7565 -1.4087 0.026 Uiso 1 1 calc R . . C9 C -0.72364(6) 0.6302(3) -1.1586(3) 0.0215(5) Uani 1 1 d . . . C10 C -0.65877(7) 0.4163(3) -0.4761(3) 0.0301(5) Uani 1 1 d . . . H10A H -0.6886 0.4231 -0.4854 0.045 Uiso 1 1 calc R . . H10B H -0.6506 0.4194 -0.3460 0.045 Uiso 1 1 calc R . . H10C H -0.6494 0.3114 -0.5317 0.045 Uiso 1 1 calc R . . C11 C -0.56445(7) 0.8984(3) -0.6547(3) 0.0324(5) Uani 1 1 d . . . H11A H -0.5514 0.8961 -0.5330 0.049 Uiso 1 1 calc R . . H11B H -0.5753 1.0106 -0.6784 0.049 Uiso 1 1 calc R . . H11C H -0.5444 0.8700 -0.7494 0.049 Uiso 1 1 calc R . . C12 C -0.66786(6) 0.9850(3) -1.3672(3) 0.0267(5) Uani 1 1 d . . . H12A H -0.6781 0.9755 -1.4939 0.040 Uiso 1 1 calc R . . H12B H -0.6380 0.9836 -1.3679 0.040 Uiso 1 1 calc R . . H12C H -0.6774 1.0902 -1.3131 0.040 Uiso 1 1 calc R . . C13 C -0.75669(7) 0.5029(3) -1.1461(3) 0.0314(5) Uani 1 1 d . . . H13A H -0.7458 0.3927 -1.1790 0.047 Uiso 1 1 calc R . . H13B H -0.7788 0.5326 -1.2312 0.047 Uiso 1 1 calc R . . H13C H -0.7672 0.4997 -1.0198 0.047 Uiso 1 1 calc R . . C14 C -0.60908(6) 0.9665(3) -1.0268(3) 0.0192(4) Uani 1 1 d . . . C15 C -0.57142(6) 0.9294(3) -1.1067(2) 0.0198(4) Uani 1 1 d . . . H15 H -0.5633 0.8164 -1.1237 0.024 Uiso 1 1 calc R . . C16 C -0.54598(6) 1.0594(3) -1.1610(3) 0.0231(5) Uani 1 1 d . . . H16 H -0.5204 1.0347 -1.2155 0.028 Uiso 1 1 calc R . . C17 C -0.55756(6) 1.2253(3) -1.1364(3) 0.0211(4) Uani 1 1 d . . . C18 C -0.59519(6) 1.2618(3) -1.0568(3) 0.0221(4) Uani 1 1 d . . . H18 H -0.6033 1.3749 -1.0402 0.026 Uiso 1 1 calc R . . C19 C -0.62072(6) 1.1333(2) -1.0019(3) 0.0220(5) Uani 1 1 d . . . H19 H -0.6463 1.1585 -0.9469 0.026 Uiso 1 1 calc R . . C20 C -0.53042(6) 1.3663(3) -1.1897(3) 0.0231(5) Uani 1 1 d . . . C21 C -0.46462(6) 1.4394(3) -1.2979(3) 0.0343(6) Uani 1 1 d . . . H21A H -0.4757 1.5085 -1.3979 0.051 Uiso 1 1 calc R . . H21B H -0.4393 1.3862 -1.3388 0.051 Uiso 1 1 calc R . . H21C H -0.4590 1.5100 -1.1903 0.051 Uiso 1 1 calc R . . B1 B -0.69273(7) 0.5536(3) -0.8416(3) 0.0207(5) 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 F1 0.0321(7) 0.0169(7) 0.0354(6) 0.0010(5) 0.0010(5) 0.0005(5) F2 0.0206(6) 0.0260(7) 0.0261(6) 0.0014(5) 0.0069(5) -0.0003(5) O1 0.0323(9) 0.0231(9) 0.0383(8) 0.0055(6) -0.0043(7) -0.0043(7) O2 0.0220(8) 0.0327(9) 0.0385(8) 0.0099(7) 0.0016(7) -0.0063(7) N1 0.0201(8) 0.0181(10) 0.0214(8) 0.0028(7) 0.0043(7) 0.0033(7) N2 0.0174(8) 0.0196(9) 0.0218(8) -0.0017(7) 0.0023(7) -0.0004(7) C1 0.0256(11) 0.0219(12) 0.0238(10) 0.0039(9) 0.0038(9) 0.0089(9) C2 0.0219(10) 0.0285(12) 0.0213(10) 0.0010(9) -0.0006(8) 0.0072(10) C3 0.0197(10) 0.0257(12) 0.0241(10) -0.0041(9) 0.0015(8) 0.0030(10) C4 0.0174(9) 0.0203(11) 0.0216(10) 0.0008(8) 0.0042(8) 0.0020(9) C5 0.0186(10) 0.0168(10) 0.0201(9) -0.0018(8) 0.0072(8) 0.0041(9) C6 0.0180(9) 0.0165(11) 0.0224(9) 0.0010(8) 0.0047(8) 0.0006(9) C7 0.0212(10) 0.0196(11) 0.0223(10) 0.0001(8) 0.0034(8) 0.0031(9) C8 0.0226(10) 0.0261(12) 0.0173(9) -0.0007(9) -0.0001(8) 0.0007(10) C9 0.0197(10) 0.0214(12) 0.0233(10) -0.0042(9) 0.0021(8) 0.0021(9) C10 0.0344(12) 0.0256(13) 0.0302(11) 0.0087(9) 0.0054(9) 0.0031(11) C11 0.0281(11) 0.0419(15) 0.0273(11) 0.0005(10) -0.0040(9) -0.0047(11) C12 0.0257(11) 0.0269(13) 0.0275(11) 0.0042(9) -0.0002(9) 0.0001(10) C13 0.0283(12) 0.0314(14) 0.0345(11) -0.0016(10) -0.0035(10) -0.0079(11) C14 0.0192(10) 0.0198(11) 0.0187(9) 0.0019(8) 0.0010(8) -0.0015(9) C15 0.0199(10) 0.0183(11) 0.0212(10) 0.0000(8) 0.0012(8) 0.0002(9) C16 0.0172(10) 0.0311(13) 0.0212(9) 0.0011(10) 0.0030(8) 0.0000(10) C17 0.0208(10) 0.0238(11) 0.0185(9) 0.0017(8) -0.0049(8) -0.0004(9) C18 0.0238(10) 0.0166(11) 0.0257(10) 0.0023(9) -0.0037(8) 0.0023(9) C19 0.0186(10) 0.0220(12) 0.0254(10) -0.0005(9) 0.0020(8) 0.0014(9) C20 0.0235(11) 0.0243(13) 0.0215(10) 0.0039(9) -0.0053(8) -0.0037(10) C21 0.0254(11) 0.0398(14) 0.0378(12) 0.0162(11) -0.0011(10) -0.0134(11) B1 0.0199(12) 0.0177(13) 0.0243(11) 0.0000(10) 0.0049(10) -0.0005(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 1.388(3) . ? F2 B1 1.394(3) . ? O1 C20 1.209(3) . ? O2 C20 1.343(3) . ? O2 C21 1.448(3) . ? N1 C1 1.356(3) . ? N1 C4 1.397(3) . ? N1 B1 1.549(3) . ? N2 C9 1.350(2) . ? N2 C6 1.402(3) . ? N2 B1 1.546(3) . ? C1 C2 1.394(3) . ? C1 C10 1.493(3) . ? C2 C3 1.380(3) . ? C2 H2 0.9500 . ? C3 C4 1.426(3) . ? C3 C11 1.502(3) . ? C4 C5 1.407(3) . ? C5 C6 1.389(3) . ? C5 C14 1.493(3) . ? C6 C7 1.436(3) . ? C7 C8 1.371(3) . ? C7 C12 1.499(3) . ? C8 C9 1.396(3) . ? C8 H8 0.9500 . ? C9 C13 1.489(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.397(3) . ? C14 C19 1.398(3) . ? C15 C16 1.390(3) . ? C15 H15 0.9500 . ? C16 C17 1.391(3) . ? C16 H16 0.9500 . ? C17 C18 1.395(3) . ? C17 C20 1.487(3) . ? C18 C19 1.384(3) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 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 C20 O2 C21 116.27(18) . . ? C1 N1 C4 108.43(16) . . ? C1 N1 B1 125.59(17) . . ? C4 N1 B1 125.79(16) . . ? C9 N2 C6 108.09(16) . . ? C9 N2 B1 126.10(17) . . ? C6 N2 B1 125.69(16) . . ? N1 C1 C2 108.55(18) . . ? N1 C1 C10 122.98(19) . . ? C2 C1 C10 128.43(19) . . ? C3 C2 C1 109.27(18) . . ? C3 C2 H2 125.4 . . ? C1 C2 H2 125.4 . . ? C2 C3 C4 106.00(18) . . ? C2 C3 C11 124.99(18) . . ? C4 C3 C11 129.01(18) . . ? N1 C4 C5 119.88(18) . . ? N1 C4 C3 107.75(16) . . ? C5 C4 C3 132.36(19) . . ? C6 C5 C4 121.48(19) . . ? C6 C5 C14 119.80(17) . . ? C4 C5 C14 118.72(18) . . ? C5 C6 N2 120.28(17) . . ? C5 C6 C7 132.28(18) . . ? N2 C6 C7 107.44(16) . . ? C8 C7 C6 106.20(18) . . ? C8 C7 C12 124.78(18) . . ? C6 C7 C12 128.91(18) . . ? C7 C8 C9 109.02(17) . . ? C7 C8 H8 125.5 . . ? C9 C8 H8 125.5 . . ? N2 C9 C8 109.24(17) . . ? N2 C9 C13 122.76(18) . . ? C8 C9 C13 128.00(18) . . ? C1 C10 H10A 109.5 . . ? C1 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C1 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C3 C11 H11A 109.5 . . ? C3 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C3 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C15 C14 C19 119.86(18) . . ? C15 C14 C5 119.87(18) . . ? C19 C14 C5 120.27(18) . . ? C16 C15 C14 119.36(19) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 120.80(18) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C16 C17 C18 119.6(2) . . ? C16 C17 C20 121.65(18) . . ? C18 C17 C20 118.69(19) . . ? C19 C18 C17 120.0(2) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C18 C19 C14 120.31(19) . . ? C18 C19 H19 119.8 . . ? C14 C19 H19 119.8 . . ? O1 C20 O2 123.2(2) . . ? O1 C20 C17 125.0(2) . . ? O2 C20 C17 111.77(19) . . ? O2 C21 H21A 109.5 . . ? O2 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O2 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? F1 B1 F2 109.39(17) . . ? F1 B1 N2 110.23(16) . . ? F2 B1 N2 110.13(17) . . ? F1 B1 N1 110.37(17) . . ? F2 B1 N1 110.18(16) . . ? N2 B1 N1 106.51(16) . . ? 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 C4 N1 C1 C2 0.3(2) . . . . ? B1 N1 C1 C2 -174.90(18) . . . . ? C4 N1 C1 C10 -177.63(18) . . . . ? B1 N1 C1 C10 7.1(3) . . . . ? N1 C1 C2 C3 -0.3(2) . . . . ? C10 C1 C2 C3 177.6(2) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C1 C2 C3 C11 -179.4(2) . . . . ? C1 N1 C4 C5 -179.79(18) . . . . ? B1 N1 C4 C5 -4.6(3) . . . . ? C1 N1 C4 C3 -0.3(2) . . . . ? B1 N1 C4 C3 174.94(17) . . . . ? C2 C3 C4 N1 0.1(2) . . . . ? C11 C3 C4 N1 179.5(2) . . . . ? C2 C3 C4 C5 179.5(2) . . . . ? C11 C3 C4 C5 -1.0(4) . . . . ? N1 C4 C5 C6 0.4(3) . . . . ? C3 C4 C5 C6 -178.9(2) . . . . ? N1 C4 C5 C14 -179.10(16) . . . . ? C3 C4 C5 C14 1.5(3) . . . . ? C4 C5 C6 N2 0.1(3) . . . . ? C14 C5 C6 N2 179.66(17) . . . . ? C4 C5 C6 C7 -180.0(2) . . . . ? C14 C5 C6 C7 -0.4(3) . . . . ? C9 N2 C6 C5 179.74(17) . . . . ? B1 N2 C6 C5 3.4(3) . . . . ? C9 N2 C6 C7 -0.2(2) . . . . ? B1 N2 C6 C7 -176.52(17) . . . . ? C5 C6 C7 C8 -180.0(2) . . . . ? N2 C6 C7 C8 -0.1(2) . . . . ? C5 C6 C7 C12 -3.8(4) . . . . ? N2 C6 C7 C12 176.15(19) . . . . ? C6 C7 C8 C9 0.3(2) . . . . ? C12 C7 C8 C9 -176.13(18) . . . . ? C6 N2 C9 C8 0.4(2) . . . . ? B1 N2 C9 C8 176.67(18) . . . . ? C6 N2 C9 C13 -179.35(18) . . . . ? B1 N2 C9 C13 -3.0(3) . . . . ? C7 C8 C9 N2 -0.4(2) . . . . ? C7 C8 C9 C13 179.3(2) . . . . ? C6 C5 C14 C15 -99.7(2) . . . . ? C4 C5 C14 C15 79.9(2) . . . . ? C6 C5 C14 C19 80.6(2) . . . . ? C4 C5 C14 C19 -99.8(2) . . . . ? C19 C14 C15 C16 -0.2(3) . . . . ? C5 C14 C15 C16 -179.92(18) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C15 C16 C17 C20 178.63(16) . . . . ? C16 C17 C18 C19 0.3(3) . . . . ? C20 C17 C18 C19 -178.52(17) . . . . ? C17 C18 C19 C14 -0.4(3) . . . . ? C15 C14 C19 C18 0.4(3) . . . . ? C5 C14 C19 C18 -179.94(18) . . . . ? C21 O2 C20 O1 1.7(3) . . . . ? C21 O2 C20 C17 -177.78(15) . . . . ? C16 C17 C20 O1 176.2(2) . . . . ? C18 C17 C20 O1 -5.0(3) . . . . ? C16 C17 C20 O2 -4.3(2) . . . . ? C18 C17 C20 O2 174.45(16) . . . . ? C9 N2 B1 F1 58.3(2) . . . . ? C6 N2 B1 F1 -125.99(19) . . . . ? C9 N2 B1 F2 -62.5(2) . . . . ? C6 N2 B1 F2 113.2(2) . . . . ? C9 N2 B1 N1 178.07(17) . . . . ? C6 N2 B1 N1 -6.2(2) . . . . ? C1 N1 B1 F1 -59.1(2) . . . . ? C4 N1 B1 F1 126.51(19) . . . . ? C1 N1 B1 F2 61.8(3) . . . . ? C4 N1 B1 F2 -112.6(2) . . . . ? C1 N1 B1 N2 -178.75(17) . . . . ? C4 N1 B1 N2 6.8(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.174 _refine_diff_density_min -0.150 _refine_diff_density_rms 0.033