# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is © The Royal Society of Chemistry and Owner Societies 2010 data_global _journal_coden_Cambridge 171 loop_ _publ_author_name 'Clennan, Edward' 'El-Idreesy, Tamer' _publ_contact_author_name 'Clennan, Edward' _publ_contact_author_email clennane@uwyo.edu _publ_section_title ; Computational and Experimental Evidence for the First Direct Spectroscopic Detection of the Pyrylogen Neutral Redox Partner ; # Attachment '- tt01.cif' data_tt01 _database_code_depnum_ccdc_archive 'CCDC 770737' #TrackingRef '- tt01.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C29 H23 N O, C2 H3 N, 2(B F4)' _chemical_formula_sum 'C31 H26 B2 F8 N2 O' _chemical_formula_weight 616.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' 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 30.0651(5) _cell_length_b 13.6116(2) _cell_length_c 15.4512(2) _cell_angle_alpha 90.00 _cell_angle_beta 114.351(1) _cell_angle_gamma 90.00 _cell_volume 5760.63(15) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6991 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 29.26 _exptl_crystal_description trigonal_prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.421 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2528 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9450 _exptl_absorpt_correction_T_max 0.9696 _exptl_absorpt_process_details 'SADABS V. 2007/2 (Bruker AXS Inc., 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18821 _diffrn_reflns_av_R_equivalents 0.0261 _diffrn_reflns_av_sigmaI/netI 0.0330 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 28.70 _reflns_number_total 7425 _reflns_number_gt 5793 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 V. 2.2 (Bruker AXS Inc, 2007)' _computing_cell_refinement 'Bruker APEX2 V. 2.2 (Bruker AXS Inc, 2007)' _computing_data_reduction 'Bruker SAINT V. 7.34a (Bruker AXS Inc, 2007)' _computing_structure_solution 'XS V. 2008/1 (Sheldrick, 2008)' _computing_structure_refinement 'XL V. 2008/1 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL V. 6.14 (Bruker, 2001)' _computing_publication_material 'Bruker SHELXTL V. 6.14 (Bruker, 2001)' _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^)+(0.0788P)^2^+7.5839P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 7425 _refine_ls_number_parameters 501 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0696 _refine_ls_R_factor_gt 0.0549 _refine_ls_wR_factor_ref 0.1612 _refine_ls_wR_factor_gt 0.1488 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.002 _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 0.03665(4) 0.38397(8) 0.42917(8) 0.0212(2) Uani 1 1 d . . . C1 C 0.06057(6) 0.46818(12) 0.46480(11) 0.0209(3) Uani 1 1 d . . . C2 C 0.10922(6) 0.46448(13) 0.52685(12) 0.0221(3) Uani 1 1 d . . . H2 H 0.1257(8) 0.5230(16) 0.5523(15) 0.027(5) Uiso 1 1 d . . . C3 C 0.13300(6) 0.37407(12) 0.54722(11) 0.0206(3) Uani 1 1 d . . . C4 C 0.10721(6) 0.28881(12) 0.50633(11) 0.0216(3) Uani 1 1 d . . . H4 H 0.1212(8) 0.2255(16) 0.5184(14) 0.024(5) Uiso 1 1 d . . . C5 C 0.05837(6) 0.29529(12) 0.44836(11) 0.0210(3) Uani 1 1 d . . . C6 C 0.18554(6) 0.36626(12) 0.61209(11) 0.0201(3) Uani 1 1 d . . . C7 C 0.20679(6) 0.42904(13) 0.68979(12) 0.0240(3) Uani 1 1 d . . . H7 H 0.1891(8) 0.4793(16) 0.7034(15) 0.029(5) Uiso 1 1 d . . . C8 C 0.25507(6) 0.41657(13) 0.75011(12) 0.0253(3) Uani 1 1 d . . . H8 H 0.2715(8) 0.4567(16) 0.8051(16) 0.029(5) Uiso 1 1 d . . . N1 N 0.28182(5) 0.34495(10) 0.73440(10) 0.0213(3) Uani 1 1 d . . . C9 C 0.26229(6) 0.28428(13) 0.65938(12) 0.0230(3) Uani 1 1 d . . . H9 H 0.2822(8) 0.2353(16) 0.6527(14) 0.024(5) Uiso 1 1 d . . . C10 C 0.21410(6) 0.29382(12) 0.59689(12) 0.0223(3) Uani 1 1 d . . . H10 H 0.2013(7) 0.2523(15) 0.5452(15) 0.022(5) Uiso 1 1 d . . . C11 C 0.03025(6) 0.55562(12) 0.43062(12) 0.0223(3) Uani 1 1 d . . . C12 C -0.01629(7) 0.54861(14) 0.35643(14) 0.0330(4) Uani 1 1 d . . . H12 H -0.0286(9) 0.4883(18) 0.3271(17) 0.038(6) Uiso 1 1 d . . . C13 C -0.04468(8) 0.63185(16) 0.32396(16) 0.0392(5) Uani 1 1 d . . . H13 H -0.0789(11) 0.628(2) 0.275(2) 0.056(8) Uiso 1 1 d . . . C14 C -0.02715(7) 0.72220(14) 0.36423(15) 0.0338(4) Uani 1 1 d . . . H14 H -0.0442(9) 0.7776(19) 0.3425(18) 0.041(6) Uiso 1 1 d . . . C15 C 0.01874(7) 0.72986(14) 0.43837(15) 0.0323(4) Uani 1 1 d . . . H15 H 0.0313(9) 0.7924(19) 0.4666(18) 0.041(6) Uiso 1 1 d . . . C16 C 0.04739(6) 0.64701(13) 0.47190(14) 0.0282(4) Uani 1 1 d . . . H16 H 0.0773(9) 0.6524(18) 0.5240(17) 0.039(6) Uiso 1 1 d . . . C17 C 0.02552(6) 0.21336(12) 0.40424(12) 0.0229(3) Uani 1 1 d . . . C18 C 0.04022(7) 0.11758(14) 0.43596(15) 0.0316(4) Uani 1 1 d . . . H18 H 0.0710(10) 0.1053(19) 0.4855(19) 0.047(7) Uiso 1 1 d . . . C19 C 0.00894(8) 0.03978(15) 0.39520(17) 0.0410(5) Uani 1 1 d . . . H19 H 0.0184(10) -0.029(2) 0.4174(18) 0.048(7) Uiso 1 1 d . . . C20 C -0.03672(8) 0.05644(16) 0.32221(16) 0.0388(5) Uani 1 1 d . . . H20 H -0.0576(9) 0.0052(19) 0.2919(18) 0.043(6) Uiso 1 1 d . . . C21 C -0.05116(7) 0.15088(16) 0.28988(14) 0.0320(4) Uani 1 1 d . . . H21 H -0.0813(9) 0.1640(18) 0.2381(18) 0.042(6) Uiso 1 1 d . . . C22 C -0.02061(6) 0.22984(14) 0.33114(12) 0.0265(4) Uani 1 1 d . . . H22 H -0.0315(8) 0.2960(17) 0.3064(15) 0.029(5) Uiso 1 1 d . . . C23 C 0.33448(6) 0.33482(14) 0.80038(12) 0.0259(4) Uani 1 1 d . . . H23A H 0.3500(8) 0.3942(17) 0.7969(16) 0.032(6) Uiso 1 1 d . . . H23B H 0.3467(8) 0.2836(16) 0.7752(15) 0.029(5) Uiso 1 1 d . . . C24 C 0.34137(6) 0.31273(13) 0.90049(12) 0.0244(3) Uani 1 1 d . . . C25 C 0.37070(7) 0.37401(15) 0.97415(14) 0.0333(4) Uani 1 1 d . . . H25 H 0.3838(9) 0.4336(19) 0.9580(18) 0.044(7) Uiso 1 1 d . . . C26 C 0.37890(9) 0.35171(19) 1.06709(15) 0.0443(6) Uani 1 1 d . . . H26 H 0.3994(11) 0.394(2) 1.114(2) 0.063(9) Uiso 1 1 d . . . C27 C 0.35821(9) 0.2697(2) 1.08699(15) 0.0469(6) Uani 1 1 d . . . H27 H 0.3631(11) 0.258(2) 1.148(2) 0.061(8) Uiso 1 1 d . . . C28 C 0.32870(9) 0.20912(19) 1.01427(17) 0.0445(5) Uani 1 1 d . . . H28 H 0.3129(10) 0.156(2) 1.026(2) 0.055(8) Uiso 1 1 d . . . C29 C 0.32009(7) 0.23019(15) 0.92083(15) 0.0336(4) Uani 1 1 d . . . H29 H 0.3011(8) 0.1912(17) 0.8735(16) 0.030(6) Uiso 1 1 d . . . F1 F 0.09144(4) 0.40624(10) 0.31120(8) 0.0392(3) Uani 1 1 d . . . B1 B 0.13741(7) 0.42353(15) 0.31395(14) 0.0257(4) Uani 1 1 d . . . F2 F 0.13835(5) 0.39583(10) 0.22783(9) 0.0445(3) Uani 1 1 d . . . F3 F 0.17212(5) 0.36918(10) 0.38739(9) 0.0411(3) Uani 1 1 d . . . F4 F 0.14912(5) 0.52197(9) 0.32961(10) 0.0475(3) Uani 1 1 d . . . B2 B 0.16774(8) 0.12437(16) 0.71407(15) 0.0293(4) Uani 1 1 d . . . F5 F 0.16552(6) 0.09053(10) 0.62816(9) 0.0539(4) Uani 1 1 d . . . F6 F 0.14447(7) 0.21366(11) 0.70238(11) 0.0605(4) Uani 1 1 d . . . F7 F 0.14906(7) 0.05657(12) 0.75619(12) 0.0674(5) Uani 1 1 d . . . F8 F 0.21622(6) 0.13866(15) 0.77295(13) 0.0743(5) Uani 1 1 d . . . N2 N 0.16258(8) -0.11479(14) 0.91832(14) 0.0434(4) Uani 1 1 d . . . C30 C 0.19144(8) -0.05517(15) 0.94629(13) 0.0338(4) Uani 1 1 d . . . C31 C 0.22923(9) 0.0197(2) 0.98100(18) 0.0444(5) Uani 1 1 d . . . H31A H 0.2214(13) 0.069(3) 1.014(3) 0.081(11) Uiso 1 1 d . . . H31B H 0.2566(16) -0.008(3) 1.022(3) 0.105(13) Uiso 1 1 d . . . H31C H 0.2363(13) 0.052(3) 0.929(3) 0.082(10) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0175(5) 0.0207(5) 0.0218(5) 0.0010(4) 0.0046(4) 0.0008(4) C1 0.0204(7) 0.0205(7) 0.0213(7) 0.0006(6) 0.0081(6) 0.0004(6) C2 0.0197(7) 0.0226(8) 0.0216(7) -0.0006(6) 0.0060(6) 0.0006(6) C3 0.0192(7) 0.0245(8) 0.0179(7) 0.0006(6) 0.0075(6) 0.0017(6) C4 0.0205(8) 0.0221(8) 0.0207(7) 0.0013(6) 0.0069(6) 0.0019(6) C5 0.0216(8) 0.0213(7) 0.0195(7) 0.0019(6) 0.0081(6) 0.0017(6) C6 0.0176(7) 0.0227(8) 0.0187(7) 0.0022(6) 0.0063(6) 0.0017(6) C7 0.0220(8) 0.0254(8) 0.0229(8) -0.0028(6) 0.0075(6) 0.0036(6) C8 0.0231(8) 0.0293(9) 0.0203(7) -0.0046(6) 0.0057(6) 0.0022(7) N1 0.0166(6) 0.0256(7) 0.0194(6) 0.0023(5) 0.0053(5) 0.0016(5) C9 0.0219(8) 0.0241(8) 0.0231(8) 0.0004(6) 0.0093(6) 0.0043(6) C10 0.0215(8) 0.0235(8) 0.0207(7) -0.0018(6) 0.0074(6) 0.0011(6) C11 0.0185(7) 0.0220(8) 0.0247(8) 0.0028(6) 0.0071(6) 0.0025(6) C12 0.0276(9) 0.0257(9) 0.0335(10) -0.0003(7) 0.0004(7) 0.0034(7) C13 0.0298(10) 0.0348(10) 0.0376(11) 0.0038(8) -0.0014(8) 0.0077(8) C14 0.0302(9) 0.0253(9) 0.0436(11) 0.0094(8) 0.0130(8) 0.0090(7) C15 0.0283(9) 0.0213(8) 0.0481(11) -0.0007(8) 0.0167(8) -0.0009(7) C16 0.0195(8) 0.0265(8) 0.0351(9) -0.0020(7) 0.0077(7) -0.0008(7) C17 0.0210(8) 0.0239(8) 0.0225(8) -0.0014(6) 0.0075(6) -0.0013(6) C18 0.0275(9) 0.0249(9) 0.0358(10) 0.0001(7) 0.0063(8) -0.0013(7) C19 0.0394(11) 0.0249(9) 0.0534(13) -0.0031(9) 0.0136(10) -0.0061(8) C20 0.0310(10) 0.0363(11) 0.0476(12) -0.0141(9) 0.0148(9) -0.0130(8) C21 0.0213(8) 0.0427(11) 0.0307(9) -0.0076(8) 0.0094(7) -0.0055(8) C22 0.0216(8) 0.0311(9) 0.0255(8) -0.0020(7) 0.0084(6) -0.0005(7) C23 0.0158(7) 0.0330(9) 0.0252(8) 0.0024(7) 0.0048(6) 0.0019(7) C24 0.0177(7) 0.0274(8) 0.0241(8) 0.0018(6) 0.0047(6) 0.0055(6) C25 0.0269(9) 0.0324(10) 0.0315(9) -0.0034(8) 0.0031(7) 0.0051(8) C26 0.0407(12) 0.0533(13) 0.0258(9) -0.0082(9) 0.0005(8) 0.0169(10) C27 0.0475(13) 0.0666(16) 0.0249(10) 0.0113(10) 0.0131(9) 0.0259(12) C28 0.0426(12) 0.0503(13) 0.0438(12) 0.0188(10) 0.0211(10) 0.0093(10) C29 0.0293(9) 0.0349(10) 0.0328(10) 0.0027(8) 0.0089(8) -0.0009(8) F1 0.0264(6) 0.0585(8) 0.0312(6) 0.0040(5) 0.0102(5) -0.0032(5) B1 0.0275(9) 0.0266(9) 0.0232(9) 0.0003(7) 0.0105(7) -0.0004(8) F2 0.0649(9) 0.0447(7) 0.0338(6) -0.0049(5) 0.0303(6) -0.0065(6) F3 0.0361(6) 0.0481(7) 0.0392(6) 0.0117(5) 0.0157(5) 0.0166(5) F4 0.0537(8) 0.0277(6) 0.0546(8) -0.0066(5) 0.0159(6) -0.0056(6) B2 0.0323(11) 0.0280(10) 0.0245(9) 0.0045(7) 0.0086(8) 0.0006(8) F5 0.0902(11) 0.0404(7) 0.0327(6) 0.0016(5) 0.0268(7) 0.0118(7) F6 0.0965(12) 0.0491(8) 0.0486(8) 0.0176(6) 0.0426(8) 0.0299(8) F7 0.1032(14) 0.0505(9) 0.0607(9) -0.0005(7) 0.0459(10) -0.0264(9) F8 0.0437(9) 0.0982(13) 0.0602(10) -0.0034(9) 0.0003(7) -0.0083(9) N2 0.0555(12) 0.0373(10) 0.0406(10) 0.0067(8) 0.0230(9) 0.0022(9) C30 0.0412(11) 0.0368(10) 0.0241(8) 0.0068(8) 0.0141(8) 0.0121(9) C31 0.0367(12) 0.0505(13) 0.0384(11) -0.0009(10) 0.0077(9) 0.0072(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 C1 1.3444(19) . ? O1 C5 1.3460(19) . ? O1 F1 2.9330(17) . ? C1 C2 1.380(2) . ? C1 C11 1.459(2) . ? C2 C3 1.393(2) . ? C2 H2 0.93(2) . ? C3 C4 1.394(2) . ? C3 C6 1.485(2) . ? C4 C5 1.372(2) . ? C4 F6 2.946(2) . ? C4 H4 0.94(2) . ? C5 C17 1.459(2) . ? C6 C10 1.390(2) . ? C6 C7 1.396(2) . ? C7 C8 1.374(2) . ? C7 H7 0.94(2) . ? C8 N1 1.348(2) . ? C8 H8 0.96(2) . ? N1 C9 1.345(2) . ? N1 C23 1.495(2) . ? C9 C10 1.376(2) . ? C9 H9 0.93(2) . ? C10 H10 0.92(2) . ? C11 C16 1.396(2) . ? C11 C12 1.399(2) . ? C12 C13 1.382(3) . ? C12 H12 0.94(2) . ? C13 C14 1.381(3) . ? C13 H13 0.99(3) . ? C14 C15 1.387(3) . ? C14 H14 0.90(3) . ? C15 C16 1.383(3) . ? C15 H15 0.96(3) . ? C16 H16 0.93(2) . ? C17 C18 1.399(2) . ? C17 C22 1.399(2) . ? C18 C19 1.383(3) . ? C18 H18 0.94(3) . ? C19 C20 1.390(3) . ? C19 H19 1.00(3) . ? C20 C21 1.383(3) . ? C20 H20 0.93(3) . ? C21 C22 1.386(3) . ? C21 H21 0.95(3) . ? C22 H22 0.98(2) . ? C23 C24 1.504(2) . ? C23 H23A 0.95(2) . ? C23 H23B 0.94(2) . ? C24 C29 1.391(3) . ? C24 C25 1.393(3) . ? C25 C26 1.387(3) . ? C25 H25 0.98(3) . ? C26 C27 1.373(4) . ? C26 H26 0.93(3) . ? C27 C28 1.382(4) . ? C27 H27 0.90(3) . ? C28 C29 1.388(3) . ? C28 H28 0.93(3) . ? C29 H29 0.89(2) . ? F1 B1 1.385(2) . ? B1 F4 1.381(2) . ? B1 F2 1.395(2) . ? B1 F3 1.396(2) . ? B2 F7 1.376(3) . ? B2 F6 1.377(3) . ? B2 F8 1.377(3) . ? B2 F5 1.380(2) . ? N2 C30 1.135(3) . ? C30 C31 1.454(3) . ? C31 H31A 0.93(4) . ? C31 H31B 0.89(4) . ? C31 H31C 1.01(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C5 123.06(12) . . ? C1 O1 F1 79.85(9) . . ? C5 O1 F1 83.34(9) . . ? O1 C1 C2 119.22(14) . . ? O1 C1 C11 113.47(13) . . ? C2 C1 C11 127.31(15) . . ? C1 C2 C3 119.18(15) . . ? C1 C2 H2 119.1(13) . . ? C3 C2 H2 121.6(13) . . ? C2 C3 C4 119.70(15) . . ? C2 C3 C6 121.34(14) . . ? C4 C3 C6 118.97(14) . . ? C5 C4 C3 119.21(15) . . ? C5 C4 F6 122.99(12) . . ? C3 C4 F6 85.32(10) . . ? C5 C4 H4 117.2(13) . . ? C3 C4 H4 123.5(13) . . ? F6 C4 H4 62.0(12) . . ? O1 C5 C4 119.53(14) . . ? O1 C5 C17 114.16(14) . . ? C4 C5 C17 126.31(15) . . ? C10 C6 C7 118.97(15) . . ? C10 C6 C3 119.75(14) . . ? C7 C6 C3 121.26(14) . . ? C8 C7 C6 119.25(16) . . ? C8 C7 H7 118.3(13) . . ? C6 C7 H7 122.4(13) . . ? N1 C8 C7 120.60(16) . . ? N1 C8 H8 116.4(13) . . ? C7 C8 H8 123.0(13) . . ? C9 N1 C8 121.22(14) . . ? C9 N1 C23 119.63(14) . . ? C8 N1 C23 119.13(14) . . ? N1 C9 C10 120.39(15) . . ? N1 C9 H9 117.6(13) . . ? C10 C9 H9 122.0(13) . . ? C9 C10 C6 119.56(15) . . ? C9 C10 H10 119.4(13) . . ? C6 C10 H10 121.1(13) . . ? C16 C11 C12 119.41(16) . . ? C16 C11 C1 120.24(15) . . ? C12 C11 C1 120.35(15) . . ? C13 C12 C11 120.05(18) . . ? C13 C12 H12 118.7(15) . . ? C11 C12 H12 121.2(15) . . ? C14 C13 C12 120.17(18) . . ? C14 C13 H13 118.0(16) . . ? C12 C13 H13 121.7(16) . . ? C13 C14 C15 120.26(18) . . ? C13 C14 H14 121.8(16) . . ? C15 C14 H14 117.9(16) . . ? C16 C15 C14 120.12(18) . . ? C16 C15 H15 119.1(15) . . ? C14 C15 H15 120.8(15) . . ? C15 C16 C11 119.98(17) . . ? C15 C16 H16 119.4(15) . . ? C11 C16 H16 120.5(15) . . ? C18 C17 C22 119.81(16) . . ? C18 C17 C5 119.57(15) . . ? C22 C17 C5 120.63(15) . . ? C19 C18 C17 119.78(18) . . ? C19 C18 H18 119.3(16) . . ? C17 C18 H18 120.9(16) . . ? C18 C19 C20 120.2(2) . . ? C18 C19 H19 121.2(15) . . ? C20 C19 H19 118.6(15) . . ? C21 C20 C19 120.18(18) . . ? C21 C20 H20 118.1(16) . . ? C19 C20 H20 121.7(16) . . ? C20 C21 C22 120.32(18) . . ? C20 C21 H21 122.0(15) . . ? C22 C21 H21 117.7(16) . . ? C21 C22 C17 119.68(17) . . ? C21 C22 H22 118.8(13) . . ? C17 C22 H22 121.5(13) . . ? N1 C23 C24 112.21(14) . . ? N1 C23 H23A 106.9(14) . . ? C24 C23 H23A 111.5(14) . . ? N1 C23 H23B 105.7(13) . . ? C24 C23 H23B 111.4(13) . . ? H23A C23 H23B 108.8(19) . . ? C29 C24 C25 119.60(18) . . ? C29 C24 C23 120.83(17) . . ? C25 C24 C23 119.53(17) . . ? C26 C25 C24 119.8(2) . . ? C26 C25 H25 121.8(15) . . ? C24 C25 H25 118.3(15) . . ? C27 C26 C25 120.4(2) . . ? C27 C26 H26 123.2(19) . . ? C25 C26 H26 116.4(19) . . ? C26 C27 C28 120.1(2) . . ? C26 C27 H27 119.2(19) . . ? C28 C27 H27 120.7(19) . . ? C27 C28 C29 120.3(2) . . ? C27 C28 H28 121.2(18) . . ? C29 C28 H28 118.5(18) . . ? C28 C29 C24 119.7(2) . . ? C28 C29 H29 120.7(15) . . ? C24 C29 H29 119.6(15) . . ? B1 F1 O1 143.84(11) . . ? F4 B1 F1 110.43(16) . . ? F4 B1 F2 108.99(16) . . ? F1 B1 F2 109.72(15) . . ? F4 B1 F3 108.70(16) . . ? F1 B1 F3 109.70(15) . . ? F2 B1 F3 109.27(16) . . ? F7 B2 F6 111.70(19) . . ? F7 B2 F8 108.03(18) . . ? F6 B2 F8 107.72(19) . . ? F7 B2 F5 111.33(18) . . ? F6 B2 F5 110.37(16) . . ? F8 B2 F5 107.51(19) . . ? B2 F6 C4 113.49(12) . . ? N2 C30 C31 178.4(2) . . ? C30 C31 H31A 112(2) . . ? C30 C31 H31B 108(3) . . ? H31A C31 H31B 107(3) . . ? C30 C31 H31C 114(2) . . ? H31A C31 H31C 108(3) . . ? H31B C31 H31C 108(3) . . ? 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 C8 N1 C23 C24 61.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.078 _refine_diff_density_min -0.550 _refine_diff_density_rms 0.061 # Attachment '- tt03a.cif' data_tt03a _database_code_depnum_ccdc_archive 'CCDC 770738' #TrackingRef '- tt03a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H23 N O3, 2(B F4), 2(C2 H4 O2)' _chemical_formula_sum 'C30 H31 B2 F8 N O7' _chemical_formula_weight 691.18 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7453(2) _cell_length_b 14.2435(3) _cell_length_c 14.7221(3) _cell_angle_alpha 118.767(1) _cell_angle_beta 91.692(1) _cell_angle_gamma 95.485(1) _cell_volume 1594.15(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3506 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 27.07 _exptl_crystal_description rectangular_prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.130 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9575 _exptl_absorpt_correction_T_max 0.9825 _exptl_absorpt_process_details 'SADABS (Bruker AXS Inc, 2007)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16479 _diffrn_reflns_av_R_equivalents 0.0294 _diffrn_reflns_av_sigmaI/netI 0.0493 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 28.70 _reflns_number_total 8187 _reflns_number_gt 4755 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 V. 2.2 (Bruker AXS Inc, 2007)' _computing_cell_refinement 'Bruker APEX2 V. 2.2 (Bruker AXS Inc, 2007)' _computing_data_reduction 'Bruker SAINT V. 7.34a (Bruker AXS Inc, 2007)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL V. 6.14 (Bruker, 2001)' _computing_publication_material 'Bruker SHELXTL V. 6.14 (Bruker, 2001)' _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^)+(0.0943P)^2^+0.1763P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8187 _refine_ls_number_parameters 569 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1088 _refine_ls_R_factor_gt 0.0603 _refine_ls_wR_factor_ref 0.1876 _refine_ls_wR_factor_gt 0.1586 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.036 _refine_ls_shift/su_max 0.084 _refine_ls_shift/su_mean 0.002 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 0.79079(16) 0.09418(11) 0.05497(10) 0.0318(3) Uani 1 1 d . . . C1 C 0.8833(2) 0.17050(16) 0.13776(15) 0.0301(4) Uani 1 1 d . . . C2 C 0.8838(2) 0.27696(17) 0.16331(17) 0.0327(4) Uani 1 1 d . . . H2 H 0.954(3) 0.3306(18) 0.2211(18) 0.033(6) Uiso 1 1 d . . . C3 C 0.7915(2) 0.30320(16) 0.10236(16) 0.0313(4) Uani 1 1 d . . . C4 C 0.6974(2) 0.22193(17) 0.01821(16) 0.0332(4) Uani 1 1 d . . . H4 H 0.634(3) 0.2384(18) -0.0274(18) 0.037(6) Uiso 1 1 d . . . C5 C 0.6978(2) 0.11650(16) -0.00459(15) 0.0300(4) Uani 1 1 d . . . C6 C 0.7917(2) 0.41704(16) 0.12612(16) 0.0321(4) Uani 1 1 d . A . C7 C 0.9268(3) 0.48769(18) 0.15722(19) 0.0393(5) Uani 1 1 d . . . H7 H 1.019(3) 0.468(2) 0.162(2) 0.052(7) Uiso 1 1 d . . . C8 C 0.9214(3) 0.59251(19) 0.17926(19) 0.0418(5) Uani 1 1 d . A . H8 H 1.013(4) 0.648(2) 0.202(2) 0.075(9) Uiso 1 1 d . . . N1 N 0.7859(2) 0.62710(14) 0.17233(14) 0.0364(4) Uani 1 1 d . . . C9 C 0.6537(3) 0.55997(18) 0.14099(19) 0.0415(5) Uani 1 1 d . A . H9 H 0.564(3) 0.5822(18) 0.1342(17) 0.034(6) Uiso 1 1 d . . . C10 C 0.6544(3) 0.45399(18) 0.11614(19) 0.0402(5) Uani 1 1 d . . . H10 H 0.568(3) 0.4123(19) 0.0939(18) 0.036(6) Uiso 1 1 d . . . C23 C 0.7836(3) 0.74245(18) 0.20616(19) 0.0417(5) Uani 1 1 d . A . H23A H 0.699(3) 0.754(2) 0.1763(19) 0.046(7) Uiso 1 1 d . . . H23B H 0.882(3) 0.772(2) 0.193(2) 0.050(7) Uiso 1 1 d . . . C24 C 0.7762(3) 0.80495(18) 0.32216(18) 0.0416(5) Uani 1 1 d . . . O2 O 0.7761(3) 0.76585(15) 0.37824(14) 0.0619(5) Uani 1 1 d . A . O3 O 0.7746(2) 0.90829(13) 0.35167(13) 0.0531(5) Uani 1 1 d . A . C25 C 0.7610(5) 0.9797(2) 0.4621(2) 0.0814(11) Uani 1 1 d . . . H25A H 0.8290 0.9614 0.5047 0.098 Uiso 1 1 calc R A . H25B H 0.6535 0.9707 0.4785 0.098 Uiso 1 1 calc R . . C26 C 0.8056(7) 1.0912(3) 0.4858(3) 0.1261(19) Uani 1 1 d . A . H26A H 0.7968 1.1400 0.5597 0.129 Uiso 1 1 calc R . . H26B H 0.7375 1.1089 0.4436 0.129 Uiso 1 1 calc R . . H26C H 0.9124 1.0996 0.4699 0.129 Uiso 1 1 calc R . . C11 C 0.9745(2) 0.12598(16) 0.18902(16) 0.0324(4) Uani 1 1 d . . . C12 C 0.9658(3) 0.01431(18) 0.14868(18) 0.0353(5) Uani 1 1 d . . . H12 H 0.906(3) -0.0284(18) 0.0896(18) 0.032(6) Uiso 1 1 d . . . C13 C 1.0546(3) -0.02711(19) 0.19695(19) 0.0393(5) Uani 1 1 d . . . H13 H 1.049(3) -0.105(2) 0.1636(18) 0.042(6) Uiso 1 1 d . . . C14 C 1.1496(3) 0.0411(2) 0.28530(18) 0.0410(5) Uani 1 1 d . . . H14 H 1.210(3) 0.0073(19) 0.3120(18) 0.041(6) Uiso 1 1 d . . . C15 C 1.1576(3) 0.1517(2) 0.32631(19) 0.0455(6) Uani 1 1 d . . . H15 H 1.220(3) 0.199(2) 0.387(2) 0.053(7) Uiso 1 1 d . . . C16 C 1.0704(3) 0.1943(2) 0.27836(18) 0.0405(5) Uani 1 1 d . . . H16 H 1.079(3) 0.266(2) 0.308(2) 0.046(7) Uiso 1 1 d . . . C17 C 0.6072(2) 0.02200(16) -0.08932(16) 0.0326(4) Uani 1 1 d . . . C18 C 0.5012(3) 0.03457(19) -0.15367(18) 0.0412(5) Uani 1 1 d . . . H18 H 0.484(3) 0.102(2) -0.1404(18) 0.041(6) Uiso 1 1 d . . . C19 C 0.4171(3) -0.0548(2) -0.2350(2) 0.0494(6) Uani 1 1 d . . . H19 H 0.350(4) -0.047(3) -0.280(3) 0.080(10) Uiso 1 1 d . . . C20 C 0.4368(3) -0.1569(2) -0.2538(2) 0.0480(6) Uani 1 1 d . . . H20 H 0.382(3) -0.219(2) -0.310(2) 0.046(7) Uiso 1 1 d . . . C21 C 0.5407(3) -0.1705(2) -0.19028(19) 0.0441(6) Uani 1 1 d . . . H21 H 0.555(3) -0.234(2) -0.201(2) 0.057(8) Uiso 1 1 d . . . C22 C 0.6262(3) -0.08253(17) -0.10779(17) 0.0366(5) Uani 1 1 d . . . H22 H 0.700(3) -0.095(2) -0.068(2) 0.065(9) Uiso 1 1 d . . . B1 B 0.7660(3) 0.6893(2) -0.0508(2) 0.0391(6) Uani 1 1 d . . . F1 F 0.76635(19) 0.65204(15) -0.15549(12) 0.0707(5) Uani 1 1 d . A . F2 F 0.7199(4) 0.59628(19) -0.0428(2) 0.0717(11) Uani 0.717(7) 1 d P A 1 F3 F 0.9040(3) 0.7331(3) 0.00132(17) 0.0751(16) Uani 0.717(7) 1 d P A 1 F4 F 0.6521(6) 0.7538(4) -0.0102(4) 0.0748(13) Uani 0.717(7) 1 d P A 1 F2A F 0.8552(12) 0.7921(6) -0.0247(8) 0.100(4) Uani 0.283(7) 1 d P A 2 F3A F 0.8610(13) 0.6453(9) -0.0097(6) 0.097(5) Uani 0.283(7) 1 d P A 2 F4A F 0.6428(10) 0.7145(12) -0.0002(8) 0.075(4) Uani 0.283(7) 1 d P A 2 B2 B 0.3214(3) 0.7502(3) 0.2360(3) 0.0524(7) Uani 1 1 d . . . F5 F 0.2709(10) 0.6754(7) 0.2636(8) 0.077(2) Uani 0.717(7) 1 d P A 1 F6 F 0.4080(9) 0.7144(6) 0.1550(7) 0.077(2) Uani 0.717(7) 1 d P A 1 F7 F 0.1972(10) 0.7902(6) 0.2264(7) 0.079(2) Uani 0.717(7) 1 d P A 1 F8 F 0.4324(6) 0.8210(6) 0.3069(5) 0.140(2) Uani 0.717(7) 1 d P A 1 F5A F 0.303(3) 0.6839(15) 0.2793(17) 0.070(5) Uani 0.283(7) 1 d P A 2 F6A F 0.365(3) 0.6797(19) 0.1301(16) 0.098(7) Uani 0.283(7) 1 d P A 2 F7A F 0.183(2) 0.7673(16) 0.1890(19) 0.093(7) Uani 0.283(7) 1 d P A 2 F8A F 0.3742(15) 0.8624(6) 0.3103(9) 0.083(3) Uani 0.283(7) 1 d P A 2 C27 C 0.4844(4) 0.5907(3) 0.3795(3) 0.0803(10) Uani 1 1 d . . . H27A H 0.4609 0.5450 0.3043 0.120 Uiso 1 1 calc R . . H27B H 0.5264 0.6636 0.3949 0.120 Uiso 1 1 calc R . . H27C H 0.3899 0.5940 0.4146 0.120 Uiso 1 1 calc R . . C28 C 0.5988(3) 0.5446(3) 0.4170(3) 0.0636(8) Uani 1 1 d . . . O4 O 0.6508(3) 0.45946(18) 0.35369(16) 0.0724(6) Uani 1 1 d . . . O5 O 0.6425(3) 0.59399(17) 0.51417(18) 0.0734(6) Uani 1 1 d . . . H5A H 0.7222 0.5653 0.5301 0.110 Uiso 1 1 d R . . C29 C 0.9683(4) 0.3667(3) 0.5648(2) 0.0650(8) Uani 1 1 d . . . H29A H 0.9724 0.2921 0.5105 0.097 Uiso 1 1 calc R . . H29B H 0.9212 0.3667 0.6243 0.097 Uiso 1 1 calc R . . H29C H 1.0731 0.4052 0.5870 0.097 Uiso 1 1 calc R . . C30 C 0.8757(3) 0.4209(2) 0.5235(2) 0.0528(6) Uani 1 1 d . . . O6 O 0.8566(2) 0.51866(15) 0.58213(15) 0.0667(6) Uani 1 1 d . . . O7 O 0.8153(2) 0.36643(15) 0.43091(14) 0.0625(5) Uani 1 1 d . . . H7A H 0.7499 0.4014 0.4182 0.094 Uiso 1 1 d 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 0.0328(8) 0.0297(7) 0.0347(7) 0.0163(6) 0.0035(6) 0.0086(6) C1 0.0265(10) 0.0325(10) 0.0326(10) 0.0163(9) 0.0042(8) 0.0069(8) C2 0.0281(10) 0.0348(11) 0.0393(11) 0.0205(10) 0.0038(9) 0.0076(9) C3 0.0272(10) 0.0338(10) 0.0395(11) 0.0218(9) 0.0076(8) 0.0096(8) C4 0.0316(11) 0.0362(11) 0.0370(11) 0.0213(9) 0.0036(9) 0.0079(9) C5 0.0284(10) 0.0347(11) 0.0325(10) 0.0194(9) 0.0066(8) 0.0101(8) C6 0.0323(11) 0.0326(10) 0.0365(11) 0.0202(9) 0.0036(8) 0.0072(8) C7 0.0306(11) 0.0383(12) 0.0520(13) 0.0236(11) 0.0038(10) 0.0084(9) C8 0.0366(12) 0.0376(12) 0.0534(14) 0.0241(11) 0.0055(10) 0.0031(10) N1 0.0410(10) 0.0315(9) 0.0434(10) 0.0239(8) 0.0006(8) 0.0033(8) C9 0.0352(12) 0.0401(12) 0.0577(14) 0.0303(11) -0.0023(10) 0.0086(10) C10 0.0328(12) 0.0340(11) 0.0576(14) 0.0263(11) -0.0046(10) 0.0015(10) C23 0.0545(15) 0.0311(11) 0.0460(13) 0.0242(10) 0.0007(11) 0.0048(10) C24 0.0442(13) 0.0396(12) 0.0472(13) 0.0265(11) 0.0026(10) 0.0021(10) O2 0.0899(15) 0.0545(11) 0.0521(11) 0.0345(9) 0.0054(10) 0.0093(10) O3 0.0758(13) 0.0372(9) 0.0464(10) 0.0201(8) 0.0119(9) 0.0071(8) C25 0.133(3) 0.0508(17) 0.0490(17) 0.0150(14) 0.0264(19) 0.0081(19) C26 0.225(6) 0.064(2) 0.062(2) 0.0109(19) 0.021(3) 0.009(3) C11 0.0293(10) 0.0363(11) 0.0381(11) 0.0215(9) 0.0085(8) 0.0125(8) C12 0.0313(11) 0.0345(11) 0.0440(12) 0.0219(10) 0.0020(9) 0.0062(9) C13 0.0366(12) 0.0395(12) 0.0536(14) 0.0306(11) 0.0099(10) 0.0112(10) C14 0.0398(12) 0.0533(14) 0.0477(13) 0.0357(12) 0.0115(10) 0.0202(11) C15 0.0476(14) 0.0499(14) 0.0401(13) 0.0217(11) -0.0021(11) 0.0141(11) C16 0.0464(13) 0.0370(12) 0.0395(12) 0.0183(10) 0.0014(10) 0.0142(10) C17 0.0310(10) 0.0342(10) 0.0328(10) 0.0158(9) 0.0068(8) 0.0055(8) C18 0.0376(12) 0.0391(12) 0.0471(13) 0.0208(11) -0.0005(10) 0.0081(10) C19 0.0400(13) 0.0574(16) 0.0473(14) 0.0238(12) -0.0059(11) 0.0030(12) C20 0.0444(14) 0.0428(13) 0.0438(13) 0.0128(11) -0.0011(11) -0.0045(11) C21 0.0483(14) 0.0338(12) 0.0460(13) 0.0160(10) 0.0101(11) 0.0036(10) C22 0.0360(12) 0.0366(11) 0.0394(12) 0.0194(10) 0.0076(9) 0.0079(9) B1 0.0381(14) 0.0389(13) 0.0418(14) 0.0200(11) 0.0059(11) 0.0088(11) F1 0.0591(10) 0.0960(13) 0.0476(9) 0.0264(9) 0.0030(7) 0.0160(9) F2 0.083(2) 0.0557(14) 0.0877(19) 0.0443(13) 0.0009(15) 0.0075(13) F3 0.0360(12) 0.107(3) 0.0439(13) 0.0096(16) 0.0027(9) -0.0072(16) F4 0.072(2) 0.088(2) 0.090(2) 0.0541(18) 0.0412(17) 0.052(2) F2A 0.099(6) 0.044(4) 0.127(7) 0.017(4) 0.044(6) 0.000(4) F3A 0.142(12) 0.122(9) 0.067(5) 0.060(6) 0.039(6) 0.101(10) F4A 0.025(3) 0.130(10) 0.050(4) 0.031(5) 0.000(3) -0.004(5) B2 0.0368(15) 0.068(2) 0.0643(19) 0.0406(17) 0.0060(14) 0.0093(14) F5 0.050(2) 0.121(4) 0.110(5) 0.096(3) 0.003(2) 0.0090(19) F6 0.075(3) 0.091(4) 0.102(5) 0.068(4) 0.045(3) 0.047(3) F7 0.060(3) 0.0579(18) 0.127(4) 0.048(2) 0.002(2) 0.0283(17) F8 0.071(3) 0.182(6) 0.147(4) 0.080(5) -0.044(3) -0.058(3) F5A 0.100(14) 0.081(7) 0.063(6) 0.055(5) 0.022(8) 0.053(9) F6A 0.135(16) 0.137(17) 0.061(7) 0.069(10) 0.033(8) 0.071(12) F7A 0.033(4) 0.130(15) 0.20(2) 0.144(16) 0.013(9) 0.018(7) F8A 0.109(9) 0.041(4) 0.082(6) 0.019(3) 0.018(6) -0.005(4) C27 0.0579(19) 0.101(3) 0.114(3) 0.075(2) 0.0234(19) 0.0209(18) C28 0.0519(16) 0.071(2) 0.080(2) 0.0465(18) 0.0110(15) -0.0004(15) O4 0.0788(15) 0.0735(14) 0.0614(13) 0.0292(11) 0.0074(11) 0.0144(12) O5 0.0677(14) 0.0626(13) 0.0822(16) 0.0299(12) 0.0084(12) 0.0038(10) C29 0.0674(19) 0.0724(19) 0.0579(17) 0.0351(15) 0.0012(14) 0.0034(15) C30 0.0463(14) 0.0533(15) 0.0496(15) 0.0200(13) 0.0032(12) -0.0061(12) O6 0.0669(13) 0.0465(11) 0.0609(12) 0.0080(9) -0.0002(10) -0.0048(9) O7 0.0635(12) 0.0551(11) 0.0535(11) 0.0155(9) -0.0075(9) 0.0041(9) _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 1.344(2) . ? O1 C1 1.349(2) . ? C1 C2 1.375(3) . ? C1 C11 1.459(3) . ? C2 C3 1.391(3) . ? C2 H2 0.97(2) . ? C3 C4 1.389(3) . ? C3 C6 1.485(3) . ? C4 C5 1.373(3) . ? C4 H4 0.98(2) . ? C5 C17 1.455(3) . ? C6 C7 1.384(3) . ? C6 C10 1.387(3) . ? C7 C8 1.373(3) . ? C7 H7 0.89(3) . ? C8 N1 1.345(3) . ? C8 H8 1.00(3) . ? N1 C9 1.341(3) . ? N1 C23 1.472(3) . ? N1 F3A 2.901(8) . ? C9 C10 1.372(3) . ? C9 H9 0.90(2) . ? C10 H10 0.86(2) . ? C23 C24 1.506(3) . ? C23 H23A 0.92(3) . ? C23 H23B 0.98(3) . ? C24 O2 1.198(3) . ? C24 O3 1.321(3) . ? O3 C25 1.461(3) . ? C25 C26 1.462(5) . ? C25 H25A 0.9900 . ? C25 H25B 0.9900 . ? C26 H26A 0.9800 . ? C26 H26B 0.9800 . ? C26 H26C 0.9800 . ? C11 C16 1.388(3) . ? C11 C12 1.398(3) . ? C12 C13 1.384(3) . ? C12 H12 0.90(2) . ? C13 C14 1.375(3) . ? C13 H13 0.97(2) . ? C14 C15 1.383(3) . ? C14 H14 0.94(3) . ? C15 C16 1.384(3) . ? C15 H15 0.93(3) . ? C16 H16 0.90(3) . ? C17 C18 1.390(3) . ? C17 C22 1.406(3) . ? C18 C19 1.377(3) . ? C18 H18 0.91(2) . ? C19 C20 1.372(4) . ? C19 H19 0.92(4) . ? C20 C21 1.377(4) . ? C20 H20 0.94(3) . ? C21 C22 1.381(3) . ? C21 H21 0.86(3) . ? C22 H22 0.95(3) . ? B1 F4A 1.307(11) . ? B1 F3 1.332(3) . ? B1 F1 1.368(3) . ? B1 F4 1.369(5) . ? B1 F3A 1.373(7) . ? B1 F2 1.408(3) . ? B1 F2A 1.456(7) . ? B2 F7 1.308(9) . ? B2 F8 1.337(6) . ? B2 F6 1.341(8) . ? B2 F5 1.355(9) . ? B2 F5A 1.37(2) . ? B2 F8A 1.453(10) . ? B2 F6A 1.48(2) . ? B2 F7A 1.48(2) . ? C27 C28 1.475(5) . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 O4 1.260(4) . ? C28 O5 1.279(4) . ? O5 H5A 0.9191 . ? C29 C30 1.470(4) . ? C29 H29A 0.9800 . ? C29 H29B 0.9800 . ? C29 H29C 0.9800 . ? C30 O7 1.265(3) . ? C30 O6 1.268(3) . ? O7 H7A 0.8651 . ? 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 C1 123.42(16) . . ? O1 C1 C2 118.93(18) . . ? O1 C1 C11 113.10(17) . . ? C2 C1 C11 127.96(19) . . ? C1 C2 C3 119.4(2) . . ? C1 C2 H2 118.0(13) . . ? C3 C2 H2 122.4(13) . . ? C4 C3 C2 119.64(19) . . ? C4 C3 C6 119.42(18) . . ? C2 C3 C6 120.94(19) . . ? C5 C4 C3 119.64(19) . . ? C5 C4 H4 119.4(13) . . ? C3 C4 H4 120.9(13) . . ? O1 C5 C4 118.94(18) . . ? O1 C5 C17 114.20(17) . . ? C4 C5 C17 126.85(19) . . ? C7 C6 C10 118.75(19) . . ? C7 C6 C3 121.42(18) . . ? C10 C6 C3 119.83(19) . . ? C8 C7 C6 119.5(2) . . ? C8 C7 H7 117.9(17) . . ? C6 C7 H7 122.6(17) . . ? N1 C8 C7 120.5(2) . . ? N1 C8 H8 115.1(18) . . ? C7 C8 H8 124.3(18) . . ? C9 N1 C8 121.23(19) . . ? C9 N1 C23 120.0(2) . . ? C8 N1 C23 118.7(2) . . ? C9 N1 F3A 104.0(3) . . ? C8 N1 F3A 92.6(2) . . ? C23 N1 F3A 76.2(2) . . ? N1 C9 C10 120.1(2) . . ? N1 C9 H9 121.5(14) . . ? C10 C9 H9 118.4(14) . . ? C9 C10 C6 119.9(2) . . ? C9 C10 H10 117.8(16) . . ? C6 C10 H10 122.3(16) . . ? N1 C23 C24 110.19(18) . . ? N1 C23 H23A 111.9(16) . . ? C24 C23 H23A 106.9(15) . . ? N1 C23 H23B 109.4(15) . . ? C24 C23 H23B 105.1(15) . . ? H23A C23 H23B 113(2) . . ? O2 C24 O3 126.0(2) . . ? O2 C24 C23 124.3(2) . . ? O3 C24 C23 109.67(19) . . ? C24 O3 C25 116.5(2) . . ? O3 C25 C26 108.7(3) . . ? O3 C25 H25A 109.9 . . ? C26 C25 H25A 109.9 . . ? O3 C25 H25B 109.9 . . ? C26 C25 H25B 109.9 . . ? H25A C25 H25B 108.3 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C16 C11 C12 119.5(2) . . ? C16 C11 C1 120.20(19) . . ? C12 C11 C1 120.28(19) . . ? C13 C12 C11 119.8(2) . . ? C13 C12 H12 122.1(14) . . ? C11 C12 H12 118.0(14) . . ? C14 C13 C12 120.3(2) . . ? C14 C13 H13 122.8(14) . . ? C12 C13 H13 116.8(14) . . ? C13 C14 C15 120.2(2) . . ? C13 C14 H14 115.7(14) . . ? C15 C14 H14 124.0(15) . . ? C14 C15 C16 120.1(2) . . ? C14 C15 H15 121.3(17) . . ? C16 C15 H15 118.5(17) . . ? C15 C16 C11 120.0(2) . . ? C15 C16 H16 117.0(17) . . ? C11 C16 H16 123.0(17) . . ? C18 C17 C22 119.3(2) . . ? C18 C17 C5 119.84(19) . . ? C22 C17 C5 120.89(19) . . ? C19 C18 C17 120.0(2) . . ? C19 C18 H18 119.7(15) . . ? C17 C18 H18 120.2(15) . . ? C20 C19 C18 120.7(2) . . ? C20 C19 H19 119(2) . . ? C18 C19 H19 121(2) . . ? C19 C20 C21 119.9(2) . . ? C19 C20 H20 121.3(16) . . ? C21 C20 H20 118.8(16) . . ? C20 C21 C22 120.7(2) . . ? C20 C21 H21 121(2) . . ? C22 C21 H21 118(2) . . ? C21 C22 C17 119.3(2) . . ? C21 C22 H22 118.5(17) . . ? C17 C22 H22 122.0(17) . . ? F4A B1 F3 118.9(5) . . ? F4A B1 F1 123.6(5) . . ? F3 B1 F1 113.8(2) . . ? F4A B1 F4 27.7(6) . . ? F3 B1 F4 113.7(3) . . ? F1 B1 F4 111.1(3) . . ? F4A B1 F3A 111.0(7) . . ? F3 B1 F3A 52.7(5) . . ? F1 B1 F3A 116.2(3) . . ? F4 B1 F3A 132.1(4) . . ? F4A B1 F2 77.7(7) . . ? F3 B1 F2 108.2(3) . . ? F1 B1 F2 104.2(2) . . ? F4 B1 F2 104.9(3) . . ? F3A B1 F2 56.3(6) . . ? F4A B1 F2A 105.3(7) . . ? F3 B1 F2A 50.0(5) . . ? F1 B1 F2A 93.1(5) . . ? F4 B1 F2A 82.1(4) . . ? F3A B1 F2A 102.7(8) . . ? F2 B1 F2A 157.1(6) . . ? B1 F3A N1 121.0(5) . . ? F7 B2 F8 115.6(5) . . ? F7 B2 F6 116.5(6) . . ? F8 B2 F6 96.5(5) . . ? F7 B2 F5 104.6(6) . . ? F8 B2 F5 109.3(6) . . ? F6 B2 F5 114.6(6) . . ? F7 B2 F5A 115.0(10) . . ? F8 B2 F5A 96.0(11) . . ? F6 B2 F5A 114.0(8) . . ? F5 B2 F5A 13.8(14) . . ? F7 B2 F8A 82.7(6) . . ? F8 B2 F8A 33.0(4) . . ? F6 B2 F8A 110.6(6) . . ? F5 B2 F8A 123.7(7) . . ? F5A B2 F8A 114.2(10) . . ? F7 B2 F6A 107.6(10) . . ? F8 B2 F6A 117.6(10) . . ? F6 B2 F6A 21.7(11) . . ? F5 B2 F6A 100.5(10) . . ? F5A B2 F6A 104.4(11) . . ? F8A B2 F6A 131.0(10) . . ? F7 B2 F7A 19.1(11) . . ? F8 B2 F7A 130.8(8) . . ? F6 B2 F7A 100.3(9) . . ? F5 B2 F7A 104.9(7) . . ? F5A B2 F7A 117.9(12) . . ? F8A B2 F7A 98.1(9) . . ? F6A B2 F7A 88.9(13) . . ? C28 C27 H27A 109.5 . . ? C28 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C28 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? O4 C28 O5 122.1(3) . . ? O4 C28 C27 120.0(3) . . ? O5 C28 C27 117.9(3) . . ? C28 O5 H5A 112.7 . . ? C30 C29 H29A 109.5 . . ? C30 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? C30 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? O7 C30 O6 122.7(3) . . ? O7 C30 C29 118.0(3) . . ? O6 C30 C29 119.2(2) . . ? C30 O7 H7A 110.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C23 C24 O2 1.7(4) . . . . ? N1 C23 C24 O3 179.8(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5A O6 0.92 1.73 2.639(3) 169.2 . O7 H7A O4 0.87 1.78 2.615(3) 160.4 . _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 28.70 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.423 _refine_diff_density_min -0.378 _refine_diff_density_rms 0.050