# Supplementary Material (ESI) for New Journal of Chemistry # This journal is © The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2009 data_global _journal_coden_Cambridge 440 loop_ _publ_author_name 'Nizhnik, Yakov' 'Lu, Jianjiang' 'Rosokha, Sergiy' 'Kochi, Jay' _publ_contact_author_name 'Rosokha, Sergiy' _publ_contact_author_email SROSOKHA@UH.EDU _publ_section_title ; Lewis Acid Effects on Donor/Acceptor Associations and Redox Reactions: Ternary Complexes of Heteroaromatic N-Oxides with Boron Trifluoride and Organic Donors ; # Attachment '- 4-NQO-BF3-rev.cif' data_yak10 _database_code_depnum_ccdc_archive 'CCDC 742367' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 B F3 N2 O3' _chemical_formula_sum 'C9 H6 B F3 N2 O3' _chemical_formula_weight 257.97 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.4823(9) _cell_length_b 12.217(2) _cell_length_c 15.168(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1015.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 301 _cell_measurement_theta_min 3.37 _cell_measurement_theta_max 22.38 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.687 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.159 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9688 _exptl_absorpt_correction_T_max 0.9842 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method 'omega-scan, full sphere' _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 6559 _diffrn_reflns_av_R_equivalents 0.0403 _diffrn_reflns_av_sigmaI/netI 0.0393 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 30.47 _reflns_number_total 1760 _reflns_number_gt 1317 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT & SADABS (Bruker, 2003)' _computing_structure_solution 'SHELXTL (Bruker, 2003)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'SHELXL, XCIF (Bruker, 1999)' _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^)+(0.0459P)^2^+0.0758P] 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 0.1(11) _refine_ls_number_reflns 1760 _refine_ls_number_parameters 163 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0663 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.0999 _refine_ls_wR_factor_gt 0.0904 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 N1 N 0.2937(4) 0.43710(16) 0.03922(13) 0.0298(4) Uani 1 1 d . . . N2 N 0.5562(5) 0.36041(18) 0.29004(15) 0.0390(5) Uani 1 1 d . . . O1 O 0.1995(3) 0.45981(13) -0.04244(11) 0.0350(4) Uani 1 1 d . . . O2 O 0.4052(5) 0.33663(17) 0.34593(13) 0.0524(6) Uani 1 1 d . . . O3 O 0.7785(4) 0.35384(18) 0.29984(13) 0.0528(6) Uani 1 1 d . . . C1 C 0.1791(5) 0.36447(19) 0.08851(16) 0.0325(5) Uani 1 1 d . . . H1 H 0.0389 0.3279 0.0664 0.039 Uiso 1 1 calc R . . C2 C 0.2641(5) 0.34150(19) 0.17302(16) 0.0338(6) Uani 1 1 d . . . H2 H 0.1836 0.2892 0.2091 0.041 Uiso 1 1 calc R . . C3 C 0.4641(5) 0.39517(18) 0.20270(15) 0.0306(5) Uani 1 1 d . . . C4 C 0.5861(5) 0.47659(18) 0.15309(16) 0.0290(5) Uani 1 1 d . . . C5 C 0.7863(5) 0.5410(2) 0.18195(17) 0.0356(6) Uani 1 1 d . . . H5 H 0.8505 0.5309 0.2396 0.043 Uiso 1 1 calc R . . C6 C 0.8866(5) 0.6171(2) 0.12740(18) 0.0395(6) Uani 1 1 d . . . H6 H 1.0205 0.6598 0.1474 0.047 Uiso 1 1 calc R . . C7 C 0.7950(5) 0.6335(2) 0.04170(18) 0.0395(6) Uani 1 1 d . . . H7 H 0.8702 0.6860 0.0044 0.047 Uiso 1 1 calc R . . C8 C 0.5997(6) 0.5752(2) 0.01133(16) 0.0355(6) Uani 1 1 d . . . H8 H 0.5366 0.5876 -0.0461 0.043 Uiso 1 1 calc R . . C9 C 0.4946(5) 0.49650(18) 0.06696(15) 0.0287(5) Uani 1 1 d . . . B1 B 0.2715(6) 0.3766(3) -0.11151(19) 0.0378(7) Uani 1 1 d . . . F1 F 0.5213(3) 0.37732(13) -0.12195(10) 0.0468(4) Uani 1 1 d . . . F2 F 0.1527(4) 0.40862(15) -0.18627(10) 0.0647(6) Uani 1 1 d . . . F3 F 0.1991(3) 0.27293(11) -0.08417(10) 0.0423(4) 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 N1 0.0335(10) 0.0300(10) 0.0260(10) -0.0046(8) 0.0014(9) 0.0050(10) N2 0.0575(15) 0.0322(11) 0.0272(11) -0.0026(9) -0.0011(11) 0.0006(12) O1 0.0425(10) 0.0347(9) 0.0279(8) -0.0001(7) -0.0058(8) 0.0090(9) O2 0.0774(15) 0.0529(12) 0.0269(9) 0.0064(9) 0.0047(10) -0.0173(12) O3 0.0605(13) 0.0557(13) 0.0420(12) 0.0019(10) -0.0122(11) 0.0099(12) C1 0.0316(12) 0.0316(12) 0.0343(13) -0.0045(10) 0.0043(11) -0.0032(11) C2 0.0391(14) 0.0302(12) 0.0321(13) 0.0000(10) 0.0079(11) -0.0034(12) C3 0.0420(14) 0.0265(11) 0.0233(11) -0.0027(10) 0.0037(10) 0.0046(11) C4 0.0341(12) 0.0254(11) 0.0275(12) -0.0076(9) 0.0055(10) 0.0020(11) C5 0.0385(13) 0.0336(12) 0.0347(13) -0.0098(10) 0.0024(12) 0.0000(12) C6 0.0388(13) 0.0321(12) 0.0476(16) -0.0111(12) 0.0074(13) -0.0070(12) C7 0.0514(15) 0.0298(12) 0.0374(14) -0.0049(11) 0.0147(13) -0.0065(14) C8 0.0496(15) 0.0289(12) 0.0282(12) -0.0011(10) 0.0071(11) 0.0020(12) C9 0.0332(12) 0.0247(10) 0.0283(12) -0.0041(9) 0.0041(10) 0.0025(11) B1 0.0506(18) 0.0358(14) 0.0270(14) -0.0034(12) -0.0061(13) 0.0080(15) F1 0.0540(10) 0.0436(9) 0.0428(9) -0.0044(7) 0.0134(8) 0.0011(9) F2 0.0993(16) 0.0599(11) 0.0348(9) -0.0045(8) -0.0267(10) 0.0204(11) F3 0.0485(9) 0.0361(7) 0.0423(9) -0.0059(7) -0.0058(8) -0.0025(8) _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 N1 C1 1.320(3) . ? N1 O1 1.370(3) . ? N1 C9 1.384(3) . ? N2 O2 1.220(3) . ? N2 O3 1.231(3) . ? N2 C3 1.480(3) . ? O1 B1 1.513(3) . ? C1 C2 1.393(3) . ? C1 H1 0.9500 . ? C2 C3 1.354(4) . ? C2 H2 0.9500 . ? C3 C4 1.415(3) . ? C4 C5 1.420(3) . ? C4 C9 1.420(3) . ? C5 C6 1.361(4) . ? C5 H5 0.9500 . ? C6 C7 1.408(4) . ? C6 H6 0.9500 . ? C7 C8 1.366(4) . ? C7 H7 0.9500 . ? C8 C9 1.403(3) . ? C8 H8 0.9500 . ? B1 F2 1.365(3) . ? B1 F1 1.378(4) . ? B1 F3 1.390(3) . ? 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 N1 O1 117.9(2) . . ? C1 N1 C9 124.0(2) . . ? O1 N1 C9 117.9(2) . . ? O2 N2 O3 124.9(2) . . ? O2 N2 C3 117.3(2) . . ? O3 N2 C3 117.7(2) . . ? N1 O1 B1 113.05(18) . . ? N1 C1 C2 119.8(2) . . ? N1 C1 H1 120.1 . . ? C2 C1 H1 120.1 . . ? C3 C2 C1 118.6(2) . . ? C3 C2 H2 120.7 . . ? C1 C2 H2 120.7 . . ? C2 C3 C4 123.1(2) . . ? C2 C3 N2 115.8(2) . . ? C4 C3 N2 121.1(2) . . ? C3 C4 C5 126.2(2) . . ? C3 C4 C9 116.3(2) . . ? C5 C4 C9 117.5(2) . . ? C6 C5 C4 120.2(3) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 121.0(3) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C8 C7 C6 121.1(3) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 118.5(3) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? N1 C9 C8 120.2(2) . . ? N1 C9 C4 118.1(2) . . ? C8 C9 C4 121.7(2) . . ? F2 B1 F1 112.1(3) . . ? F2 B1 F3 111.9(3) . . ? F1 B1 F3 108.9(2) . . ? F2 B1 O1 104.9(2) . . ? F1 B1 O1 109.5(2) . . ? F3 B1 O1 109.3(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.225 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.048 # Attachment '- 5-NQO-2pyrene-BF3-rev.cif' data_yak09 _database_code_depnum_ccdc_archive 'CCDC 742368' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H6 B F3 N2 O3, 2(C16 H10)' _chemical_formula_sum 'C41 H26 B F3 N2 O3' _chemical_formula_weight 662.45 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 'P 21' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 14.799(3) _cell_length_b 8.1970(14) _cell_length_c 25.036(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.744(5) _cell_angle_gamma 90.00 _cell_volume 3036.8(10) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 2390 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 20.33 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.449 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1368 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9796 _exptl_absorpt_correction_T_max 0.9877 _exptl_absorpt_process_details '(SADABS; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Bruker SMART' _diffrn_measurement_method 'omega-scan, full sphere' _diffrn_standards_number none _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 31925 _diffrn_reflns_av_R_equivalents 0.0594 _diffrn_reflns_av_sigmaI/netI 0.0995 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 0.81 _diffrn_reflns_theta_max 28.36 _reflns_number_total 14640 _reflns_number_gt 7477 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2003)' _computing_cell_refinement 'SAINT (Bruker, 2003)' _computing_data_reduction 'SAINT & SADABS (Bruker, 2003)' _computing_structure_solution 'SHELXTL (Bruker, 2003)' _computing_structure_refinement SHELXTL _computing_molecular_graphics 'XP (Bruker, 1999)' _computing_publication_material 'SHELXL, XCIF (Bruker, 1999)' _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^)+(0.0820P)^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 -0.2(11) _refine_ls_number_reflns 14640 _refine_ls_number_parameters 929 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1589 _refine_ls_R_factor_gt 0.0802 _refine_ls_wR_factor_ref 0.2143 _refine_ls_wR_factor_gt 0.1716 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _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 N1 N 0.9759(2) 0.6495(5) 0.38748(14) 0.0415(9) Uani 1 1 d . . . N2 N 0.8900(3) 0.2298(5) 0.30675(19) 0.0564(11) Uani 1 1 d . . . O1 O 1.0107(2) 0.7781(4) 0.41459(12) 0.0522(8) Uani 1 1 d . A . O2 O 0.8254(3) 0.1602(5) 0.32607(17) 0.0855(13) Uani 1 1 d . . . O3 O 0.9314(3) 0.1828(5) 0.26807(16) 0.0722(11) Uani 1 1 d . . . C1 C 0.9482(3) 0.5189(7) 0.41428(19) 0.0514(12) Uani 1 1 d . . . H1 H 0.9491 0.5202 0.4522 0.062 Uiso 1 1 calc R . . C2 C 0.9183(3) 0.3821(6) 0.38757(18) 0.0507(12) Uani 1 1 d . . . H2 H 0.8965 0.2904 0.4067 0.061 Uiso 1 1 calc R . . C3 C 0.9206(3) 0.3804(6) 0.33323(18) 0.0461(11) Uani 1 1 d . . . C4 C 0.9509(3) 0.5173(5) 0.30314(16) 0.0369(10) Uani 1 1 d . . . C5 C 0.9546(3) 0.5247(6) 0.24688(18) 0.0432(11) Uani 1 1 d . . . H5 H 0.9359 0.4337 0.2260 0.052 Uiso 1 1 calc R . . C6 C 0.9853(3) 0.6632(6) 0.22243(18) 0.0470(12) Uani 1 1 d . . . H6 H 0.9894 0.6668 0.1846 0.056 Uiso 1 1 calc R . . C7 C 1.0107(3) 0.7996(6) 0.25283(18) 0.0466(11) Uani 1 1 d . . . H7 H 1.0310 0.8952 0.2352 0.056 Uiso 1 1 calc R . . C8 C 1.0070(3) 0.7975(6) 0.30729(17) 0.0408(10) Uani 1 1 d . . . H8 H 1.0236 0.8909 0.3276 0.049 Uiso 1 1 calc R . . C9 C 0.9784(3) 0.6560(5) 0.33220(16) 0.0368(10) Uani 1 1 d . . . B1 B 0.9428(4) 0.8850(9) 0.4425(2) 0.0551(16) Uani 1 1 d . . . F1A F 0.9420(14) 0.827(2) 0.4946(4) 0.116(5) Uani 0.50(2) 1 d P A 1 F2A F 0.9830(12) 1.0264(13) 0.4475(8) 0.131(8) Uani 0.50(2) 1 d P A 1 F3A F 0.8584(5) 0.854(2) 0.4245(7) 0.095(7) Uani 0.50(2) 1 d P A 1 F2B F 0.8930(10) 0.9610(18) 0.3992(3) 0.083(5) Uani 0.50(2) 1 d P A 2 F1B F 0.9842(10) 1.011(2) 0.4624(5) 0.109(6) Uani 0.50(2) 1 d P A 2 F3B F 0.8890(12) 0.8165(13) 0.4726(8) 0.106(7) Uani 0.50(2) 1 d P A 2 N3 N 0.4953(2) 0.7379(5) 0.12714(16) 0.0458(10) Uani 1 1 d . . . N4 N 0.4138(3) 0.2906(6) 0.1918(2) 0.0622(12) Uani 1 1 d . . . O4 O 0.5257(2) 0.8817(4) 0.10727(13) 0.0598(9) Uani 1 1 d . . . O5 O 0.4205(5) 0.2573(7) 0.2375(2) 0.143(3) Uani 1 1 d . . . O6 O 0.3804(4) 0.2009(6) 0.1604(2) 0.1127(18) Uani 1 1 d . . . B2 B 0.4830(4) 0.9538(8) 0.0572(2) 0.0540(15) Uani 1 1 d . . . F4 F 0.3925(2) 0.9184(4) 0.05790(13) 0.0792(10) Uani 1 1 d . . . F5 F 0.5235(3) 0.8904(5) 0.01393(12) 0.0964(12) Uani 1 1 d . . . F6 F 0.5018(3) 1.1170(4) 0.06128(14) 0.0877(10) Uani 1 1 d . . . C10 C 0.7428(3) 0.7388(5) 0.25711(17) 0.0396(10) Uani 1 1 d . . . C11 C 0.7629(3) 0.8658(6) 0.21989(18) 0.0436(11) Uani 1 1 d . . . H11 H 0.7845 0.9676 0.2330 0.052 Uiso 1 1 calc R . . C12 C 0.7523(3) 0.8454(6) 0.16808(19) 0.0447(11) Uani 1 1 d . . . H12 H 0.7636 0.9352 0.1451 0.054 Uiso 1 1 calc R . . C13 C 0.7247(3) 0.6944(6) 0.14499(16) 0.0406(11) Uani 1 1 d . . . C14 C 0.7120(3) 0.6723(7) 0.09020(18) 0.0516(12) Uani 1 1 d . . . H14 H 0.7233 0.7595 0.0662 0.062 Uiso 1 1 calc R . . C15 C 0.6829(3) 0.5238(8) 0.07102(19) 0.0551(13) Uani 1 1 d . . . H15 H 0.6739 0.5111 0.0336 0.066 Uiso 1 1 calc R . . C16 C 0.6667(3) 0.3940(7) 0.10370(19) 0.0525(13) Uani 1 1 d . . . H16 H 0.6472 0.2933 0.0887 0.063 Uiso 1 1 calc R . . C17 C 0.6785(3) 0.4078(6) 0.1594(2) 0.0476(12) Uani 1 1 d . . . C18 C 0.6596(3) 0.2832(6) 0.1962(2) 0.0579(14) Uani 1 1 d . . . H18 H 0.6415 0.1798 0.1826 0.069 Uiso 1 1 calc R . . C19 C 0.6654(3) 0.3014(7) 0.2484(2) 0.0554(13) Uani 1 1 d . . . H19 H 0.6508 0.2128 0.2712 0.067 Uiso 1 1 calc R . . C20 C 0.6941(3) 0.4576(6) 0.27161(19) 0.0468(12) Uani 1 1 d . . . C21 C 0.7003(3) 0.4824(7) 0.32654(19) 0.0574(14) Uani 1 1 d . . . H21 H 0.6860 0.3963 0.3504 0.069 Uiso 1 1 calc R . . C22 C 0.7270(3) 0.6314(7) 0.34628(19) 0.0568(14) Uani 1 1 d . . . H22 H 0.7305 0.6470 0.3839 0.068 Uiso 1 1 calc R . . C23 C 0.7490(3) 0.7605(7) 0.31260(18) 0.0496(12) Uani 1 1 d . . . H23 H 0.7681 0.8621 0.3271 0.060 Uiso 1 1 calc R . . C24 C 0.7152(3) 0.5838(5) 0.23658(16) 0.0327(9) Uani 1 1 d . . . C25 C 0.7065(3) 0.5634(5) 0.18023(17) 0.0358(10) Uani 1 1 d . . . C26 C 0.4942(3) 0.7289(6) 0.18235(18) 0.0427(11) Uani 1 1 d . . . C27 C 0.5206(3) 0.8665(6) 0.2130(2) 0.0489(12) Uani 1 1 d . . . H27 H 0.5386 0.9648 0.1960 0.059 Uiso 1 1 calc R . . C28 C 0.5199(3) 0.8550(8) 0.2670(2) 0.0579(14) Uani 1 1 d . . . H28 H 0.5370 0.9469 0.2880 0.069 Uiso 1 1 calc R . . C29 C 0.4947(3) 0.7125(7) 0.2924(2) 0.0566(14) Uani 1 1 d . . . H29 H 0.4958 0.7074 0.3303 0.068 Uiso 1 1 calc R . . C30 C 0.4683(3) 0.5796(7) 0.2637(2) 0.0586(15) Uani 1 1 d . . . H30 H 0.4502 0.4838 0.2820 0.070 Uiso 1 1 calc R . . C31 C 0.4672(3) 0.5806(6) 0.20645(19) 0.0435(11) Uani 1 1 d . . . C32 C 0.4425(3) 0.4536(6) 0.1716(2) 0.0471(12) Uani 1 1 d . . . C33 C 0.4451(3) 0.4694(6) 0.1177(2) 0.0529(13) Uani 1 1 d . . . H33 H 0.4280 0.3811 0.0952 0.063 Uiso 1 1 calc R . . C34 C 0.4733(3) 0.6165(7) 0.0957(2) 0.0519(13) Uani 1 1 d . . . H34 H 0.4765 0.6287 0.0580 0.062 Uiso 1 1 calc R . . C35 C 0.6491(5) 0.5155(11) 0.4804(2) 0.089(2) Uani 1 1 d . . . C36 C 0.5841(5) 0.6277(10) 0.4732(2) 0.092(2) Uani 1 1 d . . . H36 H 0.5964 0.7327 0.4877 0.110 Uiso 1 1 calc R . . C37 C 0.5031(4) 0.6100(7) 0.4479(2) 0.0585(14) Uani 1 1 d . . . H37 H 0.4603 0.6963 0.4465 0.070 Uiso 1 1 calc R . . C38 C 0.4845(4) 0.4520(11) 0.4227(2) 0.087(2) Uani 1 1 d . . . C39 C 0.4110(5) 0.4276(11) 0.3984(3) 0.107(3) Uani 1 1 d . . . H39 H 0.3661 0.5098 0.3950 0.129 Uiso 1 1 calc R . . C40 C 0.3984(6) 0.2562(12) 0.3747(3) 0.098(3) Uani 1 1 d . . . H40 H 0.3437 0.2381 0.3553 0.117 Uiso 1 1 calc R . . C41 C 0.4533(4) 0.1329(13) 0.3779(2) 0.092(3) Uani 1 1 d . . . H41 H 0.4398 0.0284 0.3635 0.110 Uiso 1 1 calc R . . C42 C 0.5385(5) 0.1710(10) 0.4060(3) 0.091(2) Uani 1 1 d . . . C43 C 0.6013(5) 0.0605(11) 0.4123(3) 0.097(2) Uani 1 1 d . . . H43 H 0.5895 -0.0440 0.3973 0.117 Uiso 1 1 calc R . . C44 C 0.6805(4) 0.0800(7) 0.4378(2) 0.0601(14) Uani 1 1 d . . . H44 H 0.7225 -0.0077 0.4391 0.072 Uiso 1 1 calc R . . C45 C 0.7034(4) 0.2347(11) 0.4636(2) 0.084(2) Uani 1 1 d . . . C46 C 0.7770(5) 0.2633(12) 0.4874(3) 0.106(3) Uani 1 1 d . . . H46 H 0.8223 0.1814 0.4905 0.127 Uiso 1 1 calc R . . C47 C 0.7918(6) 0.4310(13) 0.5112(2) 0.106(3) Uani 1 1 d . . . H47 H 0.8472 0.4519 0.5295 0.128 Uiso 1 1 calc R . . C48 C 0.7306(4) 0.5525(13) 0.5078(2) 0.097(3) Uani 1 1 d . . . H48 H 0.7417 0.6571 0.5229 0.117 Uiso 1 1 calc R . . C49 C 0.6295(3) 0.3690(7) 0.45706(18) 0.0535(13) Uani 1 1 d . . . C50 C 0.5549(3) 0.3230(7) 0.42915(17) 0.0490(12) Uani 1 1 d . . . C51 C 0.1683(3) 0.3406(6) 0.27924(19) 0.0464(12) Uani 1 1 d . . . C52 C 0.1420(3) 0.2284(7) 0.3182(3) 0.0665(16) Uani 1 1 d . . . H52 H 0.1245 0.1217 0.3075 0.080 Uiso 1 1 calc R . . C53 C 0.1408(4) 0.2678(9) 0.3710(3) 0.0747(18) Uani 1 1 d . . . H53 H 0.1231 0.1883 0.3964 0.090 Uiso 1 1 calc R . . C54 C 0.1651(4) 0.4222(10) 0.3880(2) 0.0748(19) Uani 1 1 d . . . H54 H 0.1620 0.4489 0.4248 0.090 Uiso 1 1 calc R . . C55 C 0.1944(3) 0.5403(7) 0.35138(18) 0.0524(13) Uani 1 1 d . . . C56 C 0.2229(4) 0.7011(8) 0.3668(2) 0.0657(16) Uani 1 1 d . . . H56 H 0.2223 0.7307 0.4034 0.079 Uiso 1 1 calc R . . C57 C 0.2497(3) 0.8076(7) 0.3316(2) 0.0603(15) Uani 1 1 d . . . H57 H 0.2696 0.9116 0.3436 0.072 Uiso 1 1 calc R . . C58 C 0.2502(3) 0.7729(6) 0.27521(19) 0.0475(12) Uani 1 1 d . . . C59 C 0.2767(3) 0.8862(7) 0.2370(2) 0.0592(14) Uani 1 1 d . . . H59 H 0.2964 0.9914 0.2480 0.071 Uiso 1 1 calc R . . C60 C 0.2748(3) 0.8478(8) 0.1839(2) 0.0637(16) Uani 1 1 d . . . H60 H 0.2933 0.9274 0.1587 0.076 Uiso 1 1 calc R . . C61 C 0.2472(3) 0.6984(7) 0.1660(2) 0.0554(14) Uani 1 1 d . . . H61 H 0.2452 0.6762 0.1288 0.066 Uiso 1 1 calc R . . C62 C 0.2213(3) 0.5760(6) 0.20302(17) 0.0435(11) Uani 1 1 d . . . C63 C 0.1947(3) 0.4153(6) 0.18751(19) 0.0500(12) Uani 1 1 d . . . H63 H 0.1950 0.3867 0.1507 0.060 Uiso 1 1 calc R . . C64 C 0.1694(3) 0.3036(7) 0.2235(2) 0.0539(13) Uani 1 1 d . . . H64 H 0.1519 0.1979 0.2117 0.065 Uiso 1 1 calc R . . C65 C 0.1947(3) 0.4970(6) 0.29620(17) 0.0412(11) Uani 1 1 d . . . C66 C 0.2228(2) 0.6157(5) 0.25840(16) 0.0360(10) Uani 1 1 d . . . C67 C 0.0609(4) 0.5814(7) 0.04518(18) 0.0573(14) Uani 1 1 d . . . C68 C 0.1072(5) 0.7019(8) 0.0220(2) 0.0762(18) Uani 1 1 d . . . H68 H 0.0791 0.8049 0.0168 0.091 Uiso 1 1 calc R . . C69 C 0.1964(4) 0.6792(8) 0.0053(2) 0.0662(15) Uani 1 1 d . . . H69 H 0.2267 0.7676 -0.0113 0.079 Uiso 1 1 calc R . . C70 C 0.2427(5) 0.5317(9) 0.0122(2) 0.0750(18) Uani 1 1 d . . . H70 H 0.3033 0.5192 0.0009 0.090 Uiso 1 1 calc R . . C71 C 0.1948(3) 0.3994(7) 0.03698(18) 0.0535(13) Uani 1 1 d . . . C72 C 0.2347(4) 0.2471(8) 0.0454(2) 0.0611(15) Uani 1 1 d . . . H72 H 0.2952 0.2309 0.0343 0.073 Uiso 1 1 calc R . . C73 C 0.1918(3) 0.1241(7) 0.06832(18) 0.0525(13) Uani 1 1 d . . . H73 H 0.2213 0.0217 0.0720 0.063 Uiso 1 1 calc R . . C74 C 0.1008(3) 0.1434(6) 0.08768(17) 0.0520(13) Uani 1 1 d . . . C75 C 0.0539(4) 0.0218(7) 0.11438(19) 0.0605(14) Uani 1 1 d . . . H75 H 0.0814 -0.0812 0.1207 0.073 Uiso 1 1 calc R . . C76 C -0.0325(4) 0.0511(8) 0.1317(2) 0.0637(15) Uani 1 1 d . . . H76 H -0.0633 -0.0349 0.1492 0.076 Uiso 1 1 calc R . . C77 C -0.0765(3) 0.1949(7) 0.12520(19) 0.0540(13) Uani 1 1 d . . . H77 H -0.1360 0.2101 0.1381 0.065 Uiso 1 1 calc R . . C78 C -0.0306(3) 0.3210(7) 0.09869(19) 0.0580(14) Uani 1 1 d . . . C79 C -0.0708(4) 0.4739(7) 0.0901(2) 0.0647(15) Uani 1 1 d . . . H79 H -0.1299 0.4912 0.1033 0.078 Uiso 1 1 calc R . . C80 C -0.0307(3) 0.5967(7) 0.06436(18) 0.0511(12) Uani 1 1 d . . . H80 H -0.0628 0.6956 0.0586 0.061 Uiso 1 1 calc R . . C81 C 0.1071(3) 0.4252(6) 0.05347(16) 0.0417(11) Uani 1 1 d . . . C82 C 0.0571(3) 0.2995(6) 0.07928(16) 0.0426(11) 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 N1 0.042(2) 0.043(2) 0.039(2) -0.0048(19) 0.0009(16) 0.0061(18) N2 0.068(3) 0.030(2) 0.071(3) -0.003(2) -0.008(2) 0.003(2) O1 0.0513(18) 0.054(2) 0.0511(18) -0.0187(17) 0.0006(15) -0.0042(17) O2 0.102(3) 0.049(3) 0.106(3) 0.001(2) 0.017(3) -0.027(2) O3 0.091(3) 0.046(2) 0.080(3) -0.018(2) 0.001(2) -0.006(2) C1 0.059(3) 0.056(3) 0.039(2) 0.004(3) 0.006(2) 0.004(3) C2 0.065(3) 0.041(3) 0.047(3) 0.005(2) 0.009(2) 0.001(3) C3 0.048(3) 0.032(3) 0.058(3) -0.006(2) -0.001(2) 0.003(2) C4 0.040(2) 0.029(2) 0.042(2) -0.004(2) -0.0005(19) 0.0045(19) C5 0.042(2) 0.039(3) 0.049(3) -0.011(2) -0.006(2) 0.004(2) C6 0.049(3) 0.053(3) 0.039(2) -0.003(2) 0.002(2) 0.003(2) C7 0.046(3) 0.043(3) 0.050(3) 0.002(2) 0.005(2) 0.000(2) C8 0.042(2) 0.033(3) 0.048(3) -0.007(2) 0.007(2) 0.002(2) C9 0.040(2) 0.029(3) 0.040(2) -0.005(2) 0.0002(18) 0.0033(19) B1 0.062(4) 0.057(4) 0.046(3) -0.021(3) 0.002(3) 0.010(3) F1A 0.152(12) 0.153(11) 0.043(5) -0.018(6) 0.024(6) 0.011(9) F2A 0.155(13) 0.016(5) 0.223(16) 0.009(7) 0.104(12) -0.005(6) F3A 0.055(5) 0.109(12) 0.121(11) -0.063(11) -0.024(6) 0.025(6) F2B 0.107(8) 0.079(8) 0.062(5) -0.016(5) -0.018(5) 0.045(6) F1B 0.104(9) 0.141(14) 0.082(6) -0.091(8) -0.019(6) 0.007(8) F3B 0.133(13) 0.063(6) 0.125(13) 0.011(8) 0.083(11) 0.011(7) N3 0.040(2) 0.040(2) 0.057(2) 0.011(2) -0.0016(18) 0.0023(18) N4 0.048(2) 0.048(3) 0.091(4) 0.000(3) 0.012(2) -0.011(2) O4 0.062(2) 0.052(2) 0.065(2) 0.0244(19) -0.0080(17) -0.0076(18) O5 0.228(7) 0.091(4) 0.110(4) 0.050(3) -0.069(4) -0.077(4) O6 0.175(5) 0.065(3) 0.098(3) -0.013(3) 0.042(3) -0.049(3) B2 0.069(4) 0.041(4) 0.052(3) -0.001(3) -0.002(3) 0.006(3) F4 0.062(2) 0.084(3) 0.090(2) 0.035(2) -0.0121(16) 0.0063(18) F5 0.130(3) 0.103(3) 0.0578(19) -0.016(2) 0.036(2) -0.017(3) F6 0.119(3) 0.046(2) 0.097(2) 0.0129(19) -0.011(2) -0.0002(19) C10 0.032(2) 0.036(3) 0.051(3) 0.001(2) 0.0042(18) 0.0052(19) C11 0.044(2) 0.031(3) 0.056(3) -0.003(2) -0.003(2) -0.001(2) C12 0.041(2) 0.035(3) 0.058(3) 0.008(2) 0.000(2) -0.003(2) C13 0.033(2) 0.052(3) 0.037(2) 0.004(2) 0.0024(18) 0.004(2) C14 0.048(3) 0.060(3) 0.046(3) -0.003(3) 0.000(2) 0.013(2) C15 0.048(3) 0.075(4) 0.042(3) -0.015(3) -0.007(2) 0.010(3) C16 0.042(3) 0.052(3) 0.064(3) -0.024(3) -0.002(2) -0.001(2) C17 0.035(2) 0.040(3) 0.068(3) -0.012(3) -0.005(2) 0.006(2) C18 0.046(3) 0.028(3) 0.099(4) -0.007(3) 0.003(3) -0.003(2) C19 0.055(3) 0.041(3) 0.071(3) 0.017(3) 0.013(3) -0.002(2) C20 0.037(2) 0.048(3) 0.055(3) 0.013(2) 0.006(2) 0.002(2) C21 0.059(3) 0.069(4) 0.045(3) 0.014(3) 0.014(2) 0.005(3) C22 0.054(3) 0.077(4) 0.040(3) 0.002(3) 0.006(2) 0.009(3) C23 0.040(2) 0.064(4) 0.045(3) -0.013(3) 0.001(2) 0.003(2) C24 0.031(2) 0.028(2) 0.039(2) 0.0020(19) 0.0054(17) 0.0051(17) C25 0.028(2) 0.032(3) 0.047(2) -0.003(2) 0.0021(18) 0.0053(18) C26 0.031(2) 0.045(3) 0.053(3) 0.010(2) -0.0006(19) 0.006(2) C27 0.035(2) 0.041(3) 0.071(3) 0.007(3) -0.003(2) 0.003(2) C28 0.044(3) 0.073(4) 0.057(3) -0.005(3) -0.003(2) 0.004(3) C29 0.048(3) 0.066(4) 0.056(3) 0.007(3) 0.003(2) 0.000(3) C30 0.039(3) 0.065(4) 0.072(3) 0.021(3) 0.012(2) 0.005(3) C31 0.033(2) 0.036(3) 0.062(3) 0.004(2) 0.003(2) 0.0099(19) C32 0.035(2) 0.033(3) 0.074(3) 0.013(3) 0.011(2) 0.008(2) C33 0.043(3) 0.040(3) 0.076(4) 0.007(3) 0.003(2) 0.001(2) C34 0.048(3) 0.048(3) 0.060(3) 0.002(3) -0.006(2) 0.009(2) C35 0.105(6) 0.110(6) 0.053(3) 0.009(4) 0.024(4) -0.020(5) C36 0.081(5) 0.124(6) 0.071(4) 0.041(4) 0.045(4) 0.038(5) C37 0.077(4) 0.042(3) 0.057(3) 0.001(3) 0.026(3) 0.018(3) C38 0.053(3) 0.159(8) 0.050(3) 0.042(4) 0.008(3) 0.007(4) C39 0.082(5) 0.139(8) 0.102(5) 0.051(6) 0.040(4) 0.035(5) C40 0.101(6) 0.121(8) 0.072(4) -0.018(5) 0.014(4) -0.056(5) C41 0.045(3) 0.163(8) 0.067(4) 0.013(5) 0.005(3) -0.019(4) C42 0.106(6) 0.090(5) 0.079(4) 0.014(4) 0.041(4) -0.004(5) C43 0.084(5) 0.119(7) 0.090(5) 0.049(5) 0.034(4) 0.036(5) C44 0.063(3) 0.050(3) 0.068(3) 0.003(3) 0.017(3) 0.018(3) C45 0.060(4) 0.147(7) 0.046(3) 0.040(4) 0.006(3) -0.007(4) C46 0.103(6) 0.153(8) 0.062(4) 0.041(5) 0.036(4) 0.061(6) C47 0.107(6) 0.166(9) 0.045(3) -0.012(5) 0.008(4) -0.058(6) C48 0.048(3) 0.197(10) 0.047(3) 0.024(5) 0.002(3) -0.042(5) C49 0.065(3) 0.061(4) 0.035(2) 0.006(3) 0.013(2) -0.013(3) C50 0.049(3) 0.064(4) 0.034(2) -0.003(2) 0.011(2) -0.011(2) C51 0.039(2) 0.039(3) 0.061(3) 0.002(2) -0.001(2) 0.000(2) C52 0.045(3) 0.055(4) 0.099(5) 0.031(3) -0.002(3) -0.007(3) C53 0.058(3) 0.092(5) 0.074(4) 0.041(4) 0.013(3) 0.003(3) C54 0.056(3) 0.115(6) 0.053(3) 0.015(4) 0.007(3) 0.011(4) C55 0.045(3) 0.069(4) 0.043(3) 0.005(3) 0.002(2) 0.012(3) C56 0.057(3) 0.084(5) 0.056(3) -0.019(3) -0.009(3) 0.018(3) C57 0.055(3) 0.055(4) 0.070(3) -0.029(3) -0.021(3) 0.014(3) C58 0.032(2) 0.044(3) 0.066(3) 0.004(3) -0.007(2) 0.005(2) C59 0.043(3) 0.048(3) 0.087(4) 0.017(3) -0.007(3) 0.004(2) C60 0.045(3) 0.068(4) 0.078(4) 0.034(3) -0.001(3) -0.002(3) C61 0.046(3) 0.072(4) 0.048(3) 0.011(3) -0.001(2) 0.010(3) C62 0.030(2) 0.054(3) 0.047(3) 0.004(2) -0.0033(19) 0.003(2) C63 0.048(3) 0.054(3) 0.048(3) -0.015(3) -0.010(2) 0.009(2) C64 0.041(3) 0.041(3) 0.080(4) -0.019(3) -0.005(2) 0.000(2) C65 0.032(2) 0.045(3) 0.046(3) 0.004(2) -0.0023(19) 0.003(2) C66 0.025(2) 0.038(3) 0.045(2) -0.001(2) -0.0026(17) 0.0051(18) C67 0.082(4) 0.055(3) 0.035(2) 0.005(2) -0.016(2) -0.011(3) C68 0.109(5) 0.064(4) 0.055(3) 0.009(3) -0.018(3) -0.019(4) C69 0.089(4) 0.061(4) 0.048(3) 0.006(3) 0.006(3) -0.028(3) C70 0.100(4) 0.085(5) 0.040(3) -0.010(3) 0.002(3) -0.019(4) C71 0.057(3) 0.064(4) 0.040(3) -0.001(3) 0.004(2) -0.012(3) C72 0.050(3) 0.082(5) 0.051(3) -0.015(3) -0.002(2) 0.005(3) C73 0.061(3) 0.050(3) 0.047(3) -0.004(3) -0.005(2) 0.014(3) C74 0.068(3) 0.049(3) 0.038(2) 0.008(2) -0.013(2) -0.022(3) C75 0.082(4) 0.044(3) 0.056(3) 0.001(3) -0.009(3) 0.001(3) C76 0.056(3) 0.080(5) 0.055(3) 0.003(3) -0.002(3) -0.007(3) C77 0.050(3) 0.064(4) 0.048(3) 0.009(3) -0.001(2) -0.014(3) C78 0.056(3) 0.066(4) 0.051(3) -0.015(3) -0.015(2) 0.007(3) C79 0.075(4) 0.064(4) 0.055(3) -0.015(3) -0.015(3) 0.011(3) C80 0.058(3) 0.047(3) 0.048(3) 0.003(2) -0.017(2) 0.012(2) C81 0.058(3) 0.038(3) 0.029(2) 0.000(2) -0.010(2) -0.002(2) C82 0.038(2) 0.057(3) 0.032(2) -0.002(2) -0.0089(18) -0.004(2) _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 N1 C1 1.331(6) . ? N1 O1 1.352(5) . ? N1 C9 1.386(5) . ? N2 O3 1.216(5) . ? N2 O2 1.219(5) . ? N2 C3 1.470(6) . ? O1 B1 1.511(6) . ? C1 C2 1.376(7) . ? C1 H1 0.9500 . ? C2 C3 1.361(6) . ? C2 H2 0.9500 . ? C3 C4 1.427(6) . ? C4 C9 1.407(6) . ? C4 C5 1.412(6) . ? C5 C6 1.370(7) . ? C5 H5 0.9500 . ? C6 C7 1.401(7) . ? C6 H6 0.9500 . ? C7 C8 1.365(6) . ? C7 H7 0.9500 . ? C8 C9 1.386(6) . ? C8 H8 0.9500 . ? B1 F3B 1.238(11) . ? B1 F1B 1.295(14) . ? B1 F2A 1.308(13) . ? B1 F3A 1.348(9) . ? B1 F1A 1.389(13) . ? B1 F2B 1.445(10) . ? N3 C34 1.307(6) . ? N3 O4 1.358(5) . ? N3 C26 1.385(6) . ? N4 O5 1.179(6) . ? N4 O6 1.181(6) . ? N4 C32 1.492(6) . ? O4 B2 1.517(7) . ? B2 F5 1.348(7) . ? B2 F6 1.371(7) . ? B2 F4 1.371(7) . ? C10 C23 1.402(6) . ? C10 C24 1.428(6) . ? C10 C11 1.431(6) . ? C11 C12 1.315(6) . ? C11 H11 0.9500 . ? C12 C13 1.424(6) . ? C12 H12 0.9500 . ? C13 C14 1.394(6) . ? C13 C25 1.418(6) . ? C14 C15 1.375(7) . ? C14 H14 0.9500 . ? C15 C16 1.366(7) . ? C15 H15 0.9500 . ? C16 C17 1.408(6) . ? C16 H16 0.9500 . ? C17 C18 1.406(7) . ? C17 C25 1.437(6) . ? C18 C19 1.318(7) . ? C18 H18 0.9500 . ? C19 C20 1.466(7) . ? C19 H19 0.9500 . ? C20 C21 1.392(7) . ? C20 C24 1.394(6) . ? C21 C22 1.374(8) . ? C21 H21 0.9500 . ? C22 C23 1.394(7) . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? C24 C25 1.425(6) . ? C26 C27 1.416(7) . ? C26 C31 1.417(7) . ? C27 C28 1.357(7) . ? C27 H27 0.9500 . ? C28 C29 1.382(7) . ? C28 H28 0.9500 . ? C29 C30 1.360(7) . ? C29 H29 0.9500 . ? C30 C31 1.433(7) . ? C30 H30 0.9500 . ? C31 C32 1.404(7) . ? C32 C33 1.358(7) . ? C33 C34 1.391(7) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 C36 1.341(9) . ? C35 C49 1.365(9) . ? C35 C48 1.412(9) . ? C36 C37 1.357(9) . ? C36 H36 0.9500 . ? C37 C38 1.465(9) . ? C37 H37 0.9500 . ? C38 C39 1.255(9) . ? C38 C50 1.491(9) . ? C39 C40 1.536(11) . ? C39 H39 0.9500 . ? C40 C41 1.299(11) . ? C40 H40 0.9500 . ? C41 C42 1.469(9) . ? C41 H41 0.9500 . ? C42 C43 1.306(9) . ? C42 C50 1.393(9) . ? C43 C44 1.337(9) . ? C43 H43 0.9500 . ? C44 C45 1.460(9) . ? C44 H44 0.9500 . ? C45 C46 1.258(10) . ? C45 C49 1.558(9) . ? C46 C47 1.513(12) . ? C46 H46 0.9500 . ? C47 C48 1.348(12) . ? C47 H47 0.9500 . ? C48 H48 0.9500 . ? C49 C50 1.353(7) . ? C51 C52 1.400(7) . ? C51 C65 1.404(7) . ? C51 C64 1.429(7) . ? C52 C53 1.361(8) . ? C52 H52 0.9500 . ? C53 C54 1.382(9) . ? C53 H53 0.9500 . ? C54 C55 1.405(8) . ? C54 H54 0.9500 . ? C55 C65 1.426(6) . ? C55 C56 1.435(8) . ? C56 C57 1.306(8) . ? C56 H56 0.9500 . ? C57 C58 1.439(7) . ? C57 H57 0.9500 . ? C58 C59 1.393(7) . ? C58 C66 1.413(6) . ? C59 C60 1.366(8) . ? C59 H59 0.9500 . ? C60 C61 1.365(8) . ? C60 H60 0.9500 . ? C61 C62 1.422(7) . ? C61 H61 0.9500 . ? C62 C66 1.424(6) . ? C62 C63 1.427(7) . ? C63 C64 1.341(7) . ? C63 H63 0.9500 . ? C64 H64 0.9500 . ? C65 C66 1.423(6) . ? C67 C68 1.338(7) . ? C67 C80 1.450(7) . ? C67 C81 1.465(7) . ? C68 C69 1.402(8) . ? C68 H68 0.9500 . ? C69 C70 1.399(9) . ? C69 H69 0.9500 . ? C70 C71 1.440(8) . ? C70 H70 0.9500 . ? C71 C81 1.384(6) . ? C71 C72 1.396(8) . ? C72 C73 1.326(7) . ? C72 H72 0.9500 . ? C73 C74 1.445(7) . ? C73 H73 0.9500 . ? C74 C75 1.391(7) . ? C74 C82 1.448(7) . ? C75 C76 1.376(7) . ? C75 H75 0.9500 . ? C76 C77 1.355(8) . ? C76 H76 0.9500 . ? C77 C78 1.408(7) . ? C77 H77 0.9500 . ? C78 C79 1.402(8) . ? C78 C82 1.403(7) . ? C79 C80 1.338(8) . ? C79 H79 0.9500 . ? C80 H80 0.9500 . ? C81 C82 1.428(6) . ? 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 N1 O1 119.5(4) . . ? C1 N1 C9 123.1(4) . . ? O1 N1 C9 117.2(4) . . ? O3 N2 O2 125.1(5) . . ? O3 N2 C3 118.0(4) . . ? O2 N2 C3 116.9(5) . . ? N1 O1 B1 115.7(4) . . ? N1 C1 C2 120.6(4) . . ? N1 C1 H1 119.7 . . ? C2 C1 H1 119.7 . . ? C3 C2 C1 118.8(5) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 122.1(4) . . ? C2 C3 N2 116.6(5) . . ? C4 C3 N2 121.3(4) . . ? C9 C4 C5 117.8(4) . . ? C9 C4 C3 116.9(4) . . ? C5 C4 C3 125.2(4) . . ? C6 C5 C4 119.9(4) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.4(4) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? C8 C7 C6 121.2(5) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 118.5(4) . . ? C7 C8 H8 120.8 . . ? C9 C8 H8 120.8 . . ? C8 C9 N1 119.6(4) . . ? C8 C9 C4 122.1(4) . . ? N1 C9 C4 118.3(4) . . ? F3B B1 F1B 115.5(11) . . ? F3B B1 F2A 129.8(10) . . ? F1B B1 F2A 17.5(11) . . ? F3B B1 F3A 61.1(8) . . ? F1B B1 F3A 135.5(10) . . ? F2A B1 F3A 128.3(11) . . ? F3B B1 F1A 42.1(8) . . ? F1B B1 F1A 85.5(9) . . ? F2A B1 F1A 103.0(10) . . ? F3A B1 F1A 103.3(10) . . ? F3B B1 F2B 109.2(9) . . ? F1B B1 F2B 100.4(9) . . ? F2A B1 F2B 85.2(10) . . ? F3A B1 F2B 50.9(6) . . ? F1A B1 F2B 147.5(8) . . ? F3B B1 O1 117.0(7) . . ? F1B B1 O1 109.0(8) . . ? F2A B1 O1 104.7(9) . . ? F3A B1 O1 110.6(5) . . ? F1A B1 O1 104.4(8) . . ? F2B B1 O1 103.8(5) . . ? C34 N3 O4 121.4(4) . . ? C34 N3 C26 123.7(4) . . ? O4 N3 C26 114.9(4) . . ? O5 N4 O6 122.1(5) . . ? O5 N4 C32 121.1(5) . . ? O6 N4 C32 116.7(5) . . ? N3 O4 B2 120.3(4) . . ? F5 B2 F6 110.1(5) . . ? F5 B2 F4 112.0(5) . . ? F6 B2 F4 113.8(5) . . ? F5 B2 O4 109.2(5) . . ? F6 B2 O4 103.6(4) . . ? F4 B2 O4 107.6(4) . . ? C23 C10 C24 119.0(4) . . ? C23 C10 C11 122.8(4) . . ? C24 C10 C11 118.3(4) . . ? C12 C11 C10 121.8(4) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 122.7(4) . . ? C11 C12 H12 118.6 . . ? C13 C12 H12 118.6 . . ? C14 C13 C25 119.3(4) . . ? C14 C13 C12 123.1(5) . . ? C25 C13 C12 117.5(4) . . ? C15 C14 C13 119.7(5) . . ? C15 C14 H14 120.1 . . ? C13 C14 H14 120.1 . . ? C16 C15 C14 122.5(4) . . ? C16 C15 H15 118.8 . . ? C14 C15 H15 118.8 . . ? C15 C16 C17 120.7(5) . . ? C15 C16 H16 119.6 . . ? C17 C16 H16 119.6 . . ? C18 C17 C16 124.6(5) . . ? C18 C17 C25 117.8(4) . . ? C16 C17 C25 117.5(5) . . ? C19 C18 C17 123.8(5) . . ? C19 C18 H18 118.1 . . ? C17 C18 H18 118.1 . . ? C18 C19 C20 120.5(5) . . ? C18 C19 H19 119.8 . . ? C20 C19 H19 119.8 . . ? C21 C20 C24 120.0(5) . . ? C21 C20 C19 122.3(5) . . ? C24 C20 C19 117.7(4) . . ? C22 C21 C20 120.0(5) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C23 121.7(4) . . ? C21 C22 H22 119.1 . . ? C23 C22 H22 119.1 . . ? C22 C23 C10 119.4(5) . . ? C22 C23 H23 120.3 . . ? C10 C23 H23 120.3 . . ? C20 C24 C25 121.2(4) . . ? C20 C24 C10 119.9(4) . . ? C25 C24 C10 118.9(4) . . ? C13 C25 C24 120.8(4) . . ? C13 C25 C17 120.2(4) . . ? C24 C25 C17 119.0(4) . . ? N3 C26 C27 119.4(4) . . ? N3 C26 C31 118.6(4) . . ? C27 C26 C31 122.0(4) . . ? C28 C27 C26 118.6(5) . . ? C28 C27 H27 120.7 . . ? C26 C27 H27 120.7 . . ? C27 C28 C29 121.5(5) . . ? C27 C28 H28 119.3 . . ? C29 C28 H28 119.3 . . ? C30 C29 C28 120.8(5) . . ? C30 C29 H29 119.6 . . ? C28 C29 H29 119.6 . . ? C29 C30 C31 121.6(5) . . ? C29 C30 H30 119.2 . . ? C31 C30 H30 119.2 . . ? C32 C31 C26 116.4(4) . . ? C32 C31 C30 128.1(5) . . ? C26 C31 C30 115.6(5) . . ? C33 C32 C31 122.4(4) . . ? C33 C32 N4 115.8(5) . . ? C31 C32 N4 121.7(5) . . ? C32 C33 C34 119.2(5) . . ? C32 C33 H33 120.4 . . ? C34 C33 H33 120.4 . . ? N3 C34 C33 119.7(5) . . ? N3 C34 H34 120.2 . . ? C33 C34 H34 120.2 . . ? C36 C35 C49 113.4(7) . . ? C36 C35 C48 121.6(9) . . ? C49 C35 C48 124.9(8) . . ? C35 C36 C37 128.1(8) . . ? C35 C36 H36 115.9 . . ? C37 C36 H36 115.9 . . ? C36 C37 C38 117.1(6) . . ? C36 C37 H37 121.5 . . ? C38 C37 H37 121.5 . . ? C39 C38 C37 120.4(8) . . ? C39 C38 C50 122.6(8) . . ? C37 C38 C50 117.0(5) . . ? C38 C39 C40 115.7(8) . . ? C38 C39 H39 122.2 . . ? C40 C39 H39 122.2 . . ? C41 C40 C39 127.9(8) . . ? C41 C40 H40 116.0 . . ? C39 C40 H40 116.0 . . ? C40 C41 C42 113.4(9) . . ? C40 C41 H41 123.3 . . ? C42 C41 H41 123.3 . . ? C43 C42 C50 116.8(8) . . ? C43 C42 C41 121.0(9) . . ? C50 C42 C41 122.2(7) . . ? C42 C43 C44 126.3(9) . . ? C42 C43 H43 116.8 . . ? C44 C43 H43 116.8 . . ? C43 C44 C45 120.7(6) . . ? C43 C44 H44 119.6 . . ? C45 C44 H44 119.6 . . ? C46 C45 C44 124.4(8) . . ? C46 C45 C49 121.4(8) . . ? C44 C45 C49 114.1(5) . . ? C45 C46 C47 118.4(8) . . ? C45 C46 H46 120.8 . . ? C47 C46 H46 120.8 . . ? C48 C47 C46 123.6(8) . . ? C48 C47 H47 118.2 . . ? C46 C47 H47 118.2 . . ? C47 C48 C35 116.1(9) . . ? C47 C48 H48 121.9 . . ? C35 C48 H48 121.9 . . ? C50 C49 C35 129.3(6) . . ? C50 C49 C45 115.1(5) . . ? C35 C49 C45 115.6(6) . . ? C49 C50 C42 126.8(6) . . ? C49 C50 C38 115.0(6) . . ? C42 C50 C38 118.2(6) . . ? C52 C51 C65 117.9(5) . . ? C52 C51 C64 123.2(5) . . ? C65 C51 C64 118.9(4) . . ? C53 C52 C51 121.9(6) . . ? C53 C52 H52 119.0 . . ? C51 C52 H52 119.0 . . ? C52 C53 C54 120.6(6) . . ? C52 C53 H53 119.7 . . ? C54 C53 H53 119.7 . . ? C53 C54 C55 120.8(5) . . ? C53 C54 H54 119.6 . . ? C55 C54 H54 119.6 . . ? C54 C55 C65 117.7(5) . . ? C54 C55 C56 123.3(5) . . ? C65 C55 C56 118.9(5) . . ? C57 C56 C55 121.6(5) . . ? C57 C56 H56 119.2 . . ? C55 C56 H56 119.2 . . ? C56 C57 C58 122.3(5) . . ? C56 C57 H57 118.8 . . ? C58 C57 H57 118.8 . . ? C59 C58 C66 119.0(5) . . ? C59 C58 C57 123.1(5) . . ? C66 C58 C57 117.8(5) . . ? C60 C59 C58 120.8(5) . . ? C60 C59 H59 119.6 . . ? C58 C59 H59 119.6 . . ? C61 C60 C59 121.9(5) . . ? C61 C60 H60 119.1 . . ? C59 C60 H60 119.1 . . ? C60 C61 C62 120.1(5) . . ? C60 C61 H61 119.9 . . ? C62 C61 H61 119.9 . . ? C61 C62 C66 118.2(4) . . ? C61 C62 C63 123.4(4) . . ? C66 C62 C63 118.5(4) . . ? C64 C63 C62 121.7(4) . . ? C64 C63 H63 119.1 . . ? C62 C63 H63 119.1 . . ? C63 C64 C51 121.1(5) . . ? C63 C64 H64 119.4 . . ? C51 C64 H64 119.4 . . ? C51 C65 C66 120.4(4) . . ? C51 C65 C55 121.0(5) . . ? C66 C65 C55 118.6(4) . . ? C58 C66 C65 120.7(4) . . ? C58 C66 C62 119.9(4) . . ? C65 C66 C62 119.4(4) . . ? C68 C67 C80 124.5(6) . . ? C68 C67 C81 117.8(5) . . ? C80 C67 C81 117.7(5) . . ? C67 C68 C69 121.4(6) . . ? C67 C68 H68 119.3 . . ? C69 C68 H68 119.3 . . ? C70 C69 C68 122.6(6) . . ? C70 C69 H69 118.7 . . ? C68 C69 H69 118.7 . . ? C69 C70 C71 117.4(6) . . ? C69 C70 H70 121.3 . . ? C71 C70 H70 121.3 . . ? C81 C71 C72 119.2(5) . . ? C81 C71 C70 118.8(5) . . ? C72 C71 C70 122.0(5) . . ? C73 C72 C71 122.8(5) . . ? C73 C72 H72 118.6 . . ? C71 C72 H72 118.6 . . ? C72 C73 C74 121.0(5) . . ? C72 C73 H73 119.5 . . ? C74 C73 H73 119.5 . . ? C75 C74 C73 123.8(5) . . ? C75 C74 C82 118.5(5) . . ? C73 C74 C82 117.7(4) . . ? C76 C75 C74 119.9(5) . . ? C76 C75 H75 120.1 . . ? C74 C75 H75 120.1 . . ? C77 C76 C75 124.1(6) . . ? C77 C76 H76 117.9 . . ? C75 C76 H76 117.9 . . ? C76 C77 C78 117.5(5) . . ? C76 C77 H77 121.3 . . ? C78 C77 H77 121.3 . . ? C79 C78 C82 116.8(5) . . ? C79 C78 C77 121.5(5) . . ? C82 C78 C77 121.7(5) . . ? C80 C79 C78 123.8(6) . . ? C80 C79 H79 118.1 . . ? C78 C79 H79 118.1 . . ? C79 C80 C67 121.1(5) . . ? C79 C80 H80 119.4 . . ? C67 C80 H80 119.4 . . ? C71 C81 C82 121.2(4) . . ? C71 C81 C67 121.9(5) . . ? C82 C81 C67 116.9(4) . . ? C78 C82 C81 123.6(5) . . ? C78 C82 C74 118.3(4) . . ? C81 C82 C74 118.1(4) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.644 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.053 # Attachment '- NPO-BF3-pyrene.cif' data_yak12 _database_code_depnum_ccdc_archive 'CCDC 743147' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H16 B Cl2 F3 N2 O3' _chemical_formula_weight 495.08 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' 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 7.0332(14) _cell_length_b 10.3535(19) _cell_length_c 29.588(6) _cell_angle_alpha 90.00 _cell_angle_beta 91.623(5) _cell_angle_gamma 90.00 _cell_volume 2153.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 727 _cell_measurement_theta_min 2.75 _cell_measurement_theta_max 25.69 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.527 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.356 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9322 _exptl_absorpt_correction_T_max 0.9585 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 24464 _diffrn_reflns_av_R_equivalents 0.0610 _diffrn_reflns_av_sigmaI/netI 0.0617 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 30.55 _reflns_number_total 6358 _reflns_number_gt 3107 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1069P)^2^+0.4302P] 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 6358 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1556 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.2358 _refine_ls_wR_factor_gt 0.1912 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 0.6796(3) 0.5935(2) 0.25075(7) 0.0436(5) Uani 1 1 d . . . O2 O 0.3846(3) 0.3741(3) 0.06734(8) 0.0589(7) Uani 1 1 d . . . O3 O 0.3652(4) 0.5793(3) 0.05366(8) 0.0639(7) Uani 1 1 d . . . N1 N 0.6036(3) 0.5668(2) 0.20844(8) 0.0349(5) Uani 1 1 d . . . N2 N 0.4019(3) 0.4863(3) 0.07808(9) 0.0451(6) Uani 1 1 d . . . B1 B 0.5399(5) 0.5786(3) 0.28858(11) 0.0393(8) Uani 1 1 d . . . F1 F 0.6447(3) 0.61141(19) 0.32643(6) 0.0548(5) Uani 1 1 d . . . F2 F 0.4751(3) 0.45317(16) 0.28907(6) 0.0504(5) Uani 1 1 d . . . F3 F 0.3888(3) 0.66081(17) 0.28099(6) 0.0490(5) Uani 1 1 d . . . C1 C 0.5899(4) 0.4432(3) 0.19553(10) 0.0365(6) Uani 1 1 d . . . H1 H 0.6268 0.3759 0.2158 0.044 Uiso 1 1 calc R . . C2 C 0.5219(4) 0.4148(3) 0.15262(9) 0.0368(6) Uani 1 1 d . . . H2 H 0.5091 0.3278 0.1427 0.044 Uiso 1 1 calc R . . C3 C 0.4731(4) 0.5156(3) 0.12462(10) 0.0363(6) Uani 1 1 d . . . C4 C 0.4894(4) 0.6421(3) 0.13846(10) 0.0399(7) Uani 1 1 d . . . H4 H 0.4548 0.7109 0.1186 0.048 Uiso 1 1 calc R . . C5 C 0.5563(4) 0.6664(3) 0.18134(10) 0.0409(7) Uani 1 1 d . . . H5 H 0.5693 0.7527 0.1919 0.049 Uiso 1 1 calc R . . C6 C 0.0405(4) 0.2052(3) 0.39082(10) 0.0422(7) Uani 1 1 d . . . C7 C 0.0110(5) 0.3266(3) 0.37092(12) 0.0524(8) Uani 1 1 d . . . H7 H 0.0310 0.4026 0.3884 0.063 Uiso 1 1 calc R . . C8 C -0.0472(5) 0.3368(4) 0.32598(12) 0.0551(9) Uani 1 1 d . . . H8 H -0.0664 0.4198 0.3130 0.066 Uiso 1 1 calc R . . C9 C -0.0774(4) 0.2286(4) 0.29990(11) 0.0495(8) Uani 1 1 d . . . H9 H -0.1153 0.2379 0.2690 0.059 Uiso 1 1 calc R . . C10 C -0.0532(4) 0.1048(3) 0.31824(9) 0.0397(7) Uani 1 1 d . . . C11 C -0.0876(4) -0.0122(4) 0.29258(10) 0.0462(8) Uani 1 1 d . . . H11 H -0.1286 -0.0058 0.2618 0.055 Uiso 1 1 calc R . . C12 C -0.0633(4) -0.1286(3) 0.31102(10) 0.0438(7) Uani 1 1 d . . . H12 H -0.0902 -0.2032 0.2933 0.053 Uiso 1 1 calc R . . C13 C 0.0025(4) -0.1438(3) 0.35709(10) 0.0401(7) Uani 1 1 d . . . C14 C 0.0371(5) -0.2650(3) 0.37658(11) 0.0500(8) Uani 1 1 d . . . H14 H 0.0139 -0.3410 0.3593 0.060 Uiso 1 1 calc R . . C15 C 0.1052(5) -0.2751(4) 0.42116(12) 0.0552(9) Uani 1 1 d . . . H15 H 0.1294 -0.3580 0.4338 0.066 Uiso 1 1 calc R . . C16 C 0.1375(4) -0.1671(4) 0.44696(11) 0.0496(8) Uani 1 1 d . . . H16 H 0.1827 -0.1763 0.4773 0.059 Uiso 1 1 calc R . . C17 C 0.1048(4) -0.0430(3) 0.42922(10) 0.0391(7) Uani 1 1 d . . . C18 C 0.1371(4) 0.0728(3) 0.45462(10) 0.0430(7) Uani 1 1 d . . . H18 H 0.1818 0.0664 0.4851 0.052 Uiso 1 1 calc R . . C19 C 0.1064(4) 0.1892(3) 0.43682(10) 0.0443(7) Uani 1 1 d . . . H19 H 0.1287 0.2636 0.4550 0.053 Uiso 1 1 calc R . . C20 C 0.0079(4) 0.0930(3) 0.36426(9) 0.0354(6) Uani 1 1 d . . . C21 C 0.0377(4) -0.0319(3) 0.38351(9) 0.0353(7) Uani 1 1 d . . . Cl1 Cl 0.44316(18) 0.45286(12) 0.41455(5) 0.0980(5) Uani 1 1 d . . . Cl2 Cl 0.7785(2) 0.48032(18) 0.47301(4) 0.1168(6) Uani 1 1 d . . . C22 C 0.6146(6) 0.5561(4) 0.43677(14) 0.0674(11) Uani 1 1 d . . . H22A H 0.5512 0.6261 0.4534 0.081 Uiso 1 1 calc R . . H22B H 0.6834 0.5962 0.4116 0.081 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 0.0387(12) 0.0543(13) 0.0376(11) -0.0051(9) -0.0015(9) -0.0074(10) O2 0.0574(15) 0.0673(18) 0.0517(14) -0.0178(12) -0.0038(11) -0.0006(13) O3 0.0609(16) 0.0825(19) 0.0477(14) 0.0171(13) -0.0104(12) -0.0015(14) N1 0.0308(12) 0.0376(14) 0.0365(12) 0.0000(10) 0.0038(10) -0.0027(10) N2 0.0282(13) 0.065(2) 0.0416(14) -0.0002(14) 0.0030(11) -0.0004(12) B1 0.045(2) 0.0364(19) 0.0358(17) -0.0011(14) -0.0020(14) -0.0004(15) F1 0.0601(12) 0.0633(13) 0.0405(10) -0.0050(9) -0.0104(9) -0.0083(10) F2 0.0699(13) 0.0339(10) 0.0476(11) 0.0034(8) 0.0040(9) -0.0079(9) F3 0.0519(11) 0.0440(11) 0.0510(11) -0.0024(8) 0.0010(8) 0.0092(8) C1 0.0352(15) 0.0343(16) 0.0402(15) 0.0024(12) 0.0055(12) 0.0028(12) C2 0.0386(16) 0.0340(16) 0.0381(15) -0.0035(12) 0.0053(12) 0.0002(12) C3 0.0256(14) 0.0462(18) 0.0374(15) -0.0011(13) 0.0048(11) 0.0013(12) C4 0.0321(15) 0.0418(18) 0.0460(17) 0.0122(13) 0.0040(12) 0.0062(13) C5 0.0349(16) 0.0357(16) 0.0523(18) 0.0009(14) 0.0067(13) -0.0014(12) C6 0.0347(16) 0.052(2) 0.0401(16) -0.0046(14) 0.0076(12) -0.0055(14) C7 0.051(2) 0.051(2) 0.056(2) 0.0011(16) 0.0072(16) -0.0018(16) C8 0.050(2) 0.058(2) 0.058(2) 0.0119(18) 0.0045(16) 0.0013(17) C9 0.0350(16) 0.073(2) 0.0409(17) 0.0158(17) 0.0003(13) -0.0015(16) C10 0.0245(14) 0.062(2) 0.0334(14) 0.0008(13) 0.0049(11) -0.0034(13) C11 0.0291(15) 0.079(2) 0.0302(14) -0.0046(15) 0.0022(11) -0.0088(15) C12 0.0369(16) 0.058(2) 0.0367(16) -0.0114(14) 0.0038(12) -0.0108(14) C13 0.0271(14) 0.0517(19) 0.0419(16) -0.0059(14) 0.0057(12) -0.0051(13) C14 0.0481(19) 0.049(2) 0.0532(19) -0.0054(16) 0.0062(15) -0.0024(16) C15 0.054(2) 0.049(2) 0.062(2) 0.0076(17) 0.0018(17) 0.0034(16) C16 0.0400(18) 0.066(2) 0.0421(17) 0.0054(16) -0.0028(14) 0.0027(16) C17 0.0276(14) 0.0549(19) 0.0348(15) 0.0011(13) 0.0020(11) 0.0020(13) C18 0.0340(16) 0.067(2) 0.0279(14) -0.0061(14) -0.0007(12) -0.0017(15) C19 0.0406(17) 0.055(2) 0.0374(16) -0.0110(14) 0.0014(13) -0.0078(15) C20 0.0217(13) 0.0521(18) 0.0325(14) -0.0028(12) 0.0048(10) -0.0028(12) C21 0.0226(13) 0.0514(19) 0.0320(14) -0.0049(12) 0.0028(10) -0.0028(12) Cl1 0.0757(8) 0.0837(9) 0.1358(12) -0.0468(8) 0.0243(7) -0.0145(6) Cl2 0.1019(10) 0.1811(16) 0.0678(8) 0.0388(8) 0.0085(7) 0.0451(10) C22 0.072(3) 0.064(3) 0.067(3) 0.0098(19) 0.000(2) -0.005(2) _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 N1 1.375(3) . ? O1 B1 1.518(4) . ? O2 N2 1.209(4) . ? O3 N2 1.227(4) . ? N1 C1 1.338(4) . ? N1 C5 1.342(4) . ? N2 C3 1.484(4) . ? B1 F1 1.366(4) . ? B1 F3 1.375(4) . ? B1 F2 1.376(4) . ? C1 C2 1.376(4) . ? C1 H1 0.9500 . ? C2 C3 1.371(4) . ? C2 H2 0.9500 . ? C3 C4 1.376(4) . ? C4 C5 1.364(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? C6 C7 1.401(5) . ? C6 C20 1.418(4) . ? C6 C19 1.435(4) . ? C7 C8 1.384(5) . ? C7 H7 0.9500 . ? C8 C9 1.373(5) . ? C8 H8 0.9500 . ? C9 C10 1.401(4) . ? C9 H9 0.9500 . ? C10 C20 1.422(4) . ? C10 C11 1.446(5) . ? C11 C12 1.332(5) . ? C11 H11 0.9500 . ? C12 C13 1.436(4) . ? C12 H12 0.9500 . ? C13 C14 1.399(5) . ? C13 C21 1.415(4) . ? C14 C15 1.394(5) . ? C14 H14 0.9500 . ? C15 C16 1.369(5) . ? C15 H15 0.9500 . ? C16 C17 1.404(4) . ? C16 H16 0.9500 . ? C17 C21 1.424(4) . ? C17 C18 1.430(4) . ? C18 C19 1.331(4) . ? C18 H18 0.9500 . ? C19 H19 0.9500 . ? C20 C21 1.426(4) . ? Cl1 C22 1.728(4) . ? Cl2 C22 1.739(4) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? 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 O1 B1 114.1(2) . . ? C1 N1 C5 123.3(3) . . ? C1 N1 O1 118.4(2) . . ? C5 N1 O1 118.2(2) . . ? O2 N2 O3 125.5(3) . . ? O2 N2 C3 118.0(3) . . ? O3 N2 C3 116.4(3) . . ? F1 B1 F3 112.1(3) . . ? F1 B1 F2 113.4(3) . . ? F3 B1 F2 109.4(3) . . ? F1 B1 O1 103.5(3) . . ? F3 B1 O1 109.3(2) . . ? F2 B1 O1 109.0(3) . . ? N1 C1 C2 119.3(3) . . ? N1 C1 H1 120.4 . . ? C2 C1 H1 120.4 . . ? C3 C2 C1 118.0(3) . . ? C3 C2 H2 121.0 . . ? C1 C2 H2 121.0 . . ? C2 C3 C4 121.9(3) . . ? C2 C3 N2 118.5(3) . . ? C4 C3 N2 119.6(3) . . ? C5 C4 C3 118.4(3) . . ? C5 C4 H4 120.8 . . ? C3 C4 H4 120.8 . . ? N1 C5 C4 119.2(3) . . ? N1 C5 H5 120.4 . . ? C4 C5 H5 120.4 . . ? C7 C6 C20 118.9(3) . . ? C7 C6 C19 122.8(3) . . ? C20 C6 C19 118.3(3) . . ? C8 C7 C6 120.5(3) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 121.0(3) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C8 C9 C10 120.9(3) . . ? C8 C9 H9 119.5 . . ? C10 C9 H9 119.5 . . ? C9 C10 C20 118.7(3) . . ? C9 C10 C11 123.1(3) . . ? C20 C10 C11 118.2(3) . . ? C12 C11 C10 121.7(3) . . ? C12 C11 H11 119.2 . . ? C10 C11 H11 119.2 . . ? C11 C12 C13 121.5(3) . . ? C11 C12 H12 119.2 . . ? C13 C12 H12 119.2 . . ? C14 C13 C21 118.7(3) . . ? C14 C13 C12 122.5(3) . . ? C21 C13 C12 118.7(3) . . ? C15 C14 C13 120.6(3) . . ? C15 C14 H14 119.7 . . ? C13 C14 H14 119.7 . . ? C16 C15 C14 120.9(3) . . ? C16 C15 H15 119.6 . . ? C14 C15 H15 119.6 . . ? C15 C16 C17 121.0(3) . . ? C15 C16 H16 119.5 . . ? C17 C16 H16 119.5 . . ? C16 C17 C21 118.3(3) . . ? C16 C17 C18 123.3(3) . . ? C21 C17 C18 118.4(3) . . ? C19 C18 C17 122.0(3) . . ? C19 C18 H18 119.0 . . ? C17 C18 H18 119.0 . . ? C18 C19 C6 121.6(3) . . ? C18 C19 H19 119.2 . . ? C6 C19 H19 119.2 . . ? C6 C20 C10 120.0(3) . . ? C6 C20 C21 120.2(3) . . ? C10 C20 C21 119.8(3) . . ? C13 C21 C17 120.4(3) . . ? C13 C21 C20 120.0(3) . . ? C17 C21 C20 119.6(3) . . ? Cl1 C22 Cl2 113.5(2) . . ? Cl1 C22 H22A 108.9 . . ? Cl2 C22 H22A 108.9 . . ? Cl1 C22 H22B 108.9 . . ? Cl2 C22 H22B 108.9 . . ? H22A C22 H22B 107.7 . . ? _diffrn_measured_fraction_theta_max 0.966 _diffrn_reflns_theta_full 29.90 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.656 _refine_diff_density_min -0.670 _refine_diff_density_rms 0.093 # Attachment '- NPO-BF3.cif' data_yak14 _database_code_depnum_ccdc_archive 'CCDC 743148' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H4 B F3 N2 O3' _chemical_formula_weight 207.91 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 Orthorhombic _symmetry_space_group_name_H-M 'Pca2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 11.996(3) _cell_length_b 6.0475(13) _cell_length_c 11.156(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 809.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 301 _cell_measurement_theta_min 3.37 _cell_measurement_theta_max 22.38 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.706 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_absorpt_coefficient_mu 0.177 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9655 _exptl_absorpt_correction_T_max 0.9860 _exptl_absorpt_process_details none _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 7360 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0506 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.37 _diffrn_reflns_theta_max 30.64 _reflns_number_total 2319 _reflns_number_gt 1643 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0387P)^2^+0.1787P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.1(11) _refine_ls_number_reflns 2319 _refine_ls_number_parameters 127 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0493 _refine_ls_wR_factor_ref 0.1057 _refine_ls_wR_factor_gt 0.0919 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 0.86296(15) 0.7083(3) 1.00325(17) 0.0344(4) Uani 1 1 d . . . O2 O 0.96450(17) -0.1824(4) 0.75743(19) 0.0469(6) Uani 1 1 d . . . O3 O 1.09853(16) -0.1726(3) 0.8876(2) 0.0449(5) Uani 1 1 d . . . N1 N 0.89611(16) 0.5006(3) 0.97085(19) 0.0291(4) Uani 1 1 d . . . N2 N 1.01514(18) -0.0967(4) 0.84006(19) 0.0323(5) Uani 1 1 d . . . C1 C 0.8365(2) 0.3971(4) 0.8849(2) 0.0322(5) Uani 1 1 d . . . H1 H 0.7699 0.4617 0.8550 0.039 Uiso 1 1 calc R . . C2 C 0.8729(2) 0.1977(4) 0.8413(2) 0.0326(6) Uani 1 1 d . . . H2 H 0.8326 0.1211 0.7809 0.039 Uiso 1 1 calc R . . C3 C 0.9700(2) 0.1126(4) 0.8881(2) 0.0279(5) Uani 1 1 d . . . C4 C 1.0288(2) 0.2162(4) 0.9782(2) 0.0322(6) Uani 1 1 d . . . H4 H 1.0939 0.1513 1.0115 0.039 Uiso 1 1 calc R . . C5 C 0.9897(2) 0.4168(4) 1.0180(2) 0.0325(5) Uani 1 1 d . . . H5 H 1.0288 0.4955 1.0785 0.039 Uiso 1 1 calc R . . B1 B 0.8062(2) 0.7223(5) 1.1251(3) 0.0350(6) Uani 1 1 d . . . F1 F 0.88071(15) 0.6825(4) 1.21462(16) 0.0623(6) Uani 1 1 d . . . F2 F 0.76602(12) 0.9349(2) 1.12674(19) 0.0498(4) Uani 1 1 d . . . F3 F 0.72266(11) 0.5670(2) 1.12742(18) 0.0470(4) 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 O1 0.0416(9) 0.0244(9) 0.0372(10) -0.0012(8) 0.0075(8) 0.0022(8) O2 0.0578(13) 0.0416(12) 0.0412(11) -0.0167(10) -0.0031(10) 0.0033(10) O3 0.0405(10) 0.0381(11) 0.0563(12) -0.0070(11) -0.0018(10) 0.0093(8) N1 0.0320(9) 0.0254(10) 0.0299(11) -0.0003(9) 0.0043(9) 0.0011(9) N2 0.0334(11) 0.0305(11) 0.0330(12) -0.0025(10) 0.0066(10) 0.0001(9) C1 0.0281(11) 0.0371(13) 0.0314(13) 0.0008(12) -0.0017(10) 0.0012(10) C2 0.0322(12) 0.0360(14) 0.0294(13) -0.0031(11) -0.0022(10) -0.0021(11) C3 0.0342(12) 0.0242(11) 0.0254(11) 0.0007(10) 0.0050(10) -0.0031(10) C4 0.0333(12) 0.0347(13) 0.0287(13) 0.0025(12) -0.0030(11) 0.0024(11) C5 0.0351(12) 0.0346(13) 0.0278(12) -0.0013(11) -0.0065(10) -0.0008(11) B1 0.0373(14) 0.0395(17) 0.0281(13) -0.0066(15) 0.0008(14) 0.0052(11) F1 0.0628(12) 0.0831(15) 0.0411(10) -0.0176(11) -0.0197(9) 0.0188(10) F2 0.0552(9) 0.0408(8) 0.0535(10) -0.0107(10) 0.0101(10) 0.0096(7) F3 0.0413(8) 0.0498(9) 0.0499(10) 0.0032(10) 0.0099(9) -0.0028(7) _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 N1 1.366(2) . ? O1 B1 1.523(4) . ? O2 N2 1.219(3) . ? O3 N2 1.222(3) . ? N1 C5 1.340(3) . ? N1 C1 1.350(3) . ? N2 C3 1.478(3) . ? C1 C2 1.372(4) . ? C1 H1 0.9500 . ? C2 C3 1.375(3) . ? C2 H2 0.9500 . ? C3 C4 1.378(4) . ? C4 C5 1.374(4) . ? C4 H4 0.9500 . ? C5 H5 0.9500 . ? B1 F1 1.362(4) . ? B1 F2 1.373(3) . ? B1 F3 1.374(3) . ? 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 O1 B1 114.67(19) . . ? C5 N1 C1 123.2(2) . . ? C5 N1 O1 119.2(2) . . ? C1 N1 O1 117.4(2) . . ? O2 N2 O3 125.2(2) . . ? O2 N2 C3 117.1(2) . . ? O3 N2 C3 117.7(2) . . ? N1 C1 C2 119.4(2) . . ? N1 C1 H1 120.3 . . ? C2 C1 H1 120.3 . . ? C1 C2 C3 117.7(2) . . ? C1 C2 H2 121.2 . . ? C3 C2 H2 121.2 . . ? C2 C3 C4 122.7(2) . . ? C2 C3 N2 119.5(2) . . ? C4 C3 N2 117.8(2) . . ? C5 C4 C3 117.5(2) . . ? C5 C4 H4 121.2 . . ? C3 C4 H4 121.2 . . ? N1 C5 C4 119.5(2) . . ? N1 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? F1 B1 F2 112.7(3) . . ? F1 B1 F3 110.1(3) . . ? F2 B1 F3 112.6(2) . . ? F1 B1 O1 110.6(2) . . ? F2 B1 O1 102.8(3) . . ? F3 B1 O1 107.8(2) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 29.50 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.248 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.049 # Attachment '- NPO-pyrene.cif' data_yak11 _database_code_depnum_ccdc_archive 'CCDC 743149' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H24 N2 O3' _chemical_formula_weight 544.58 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' 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 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1578(16) _cell_length_b 8.2030(16) _cell_length_c 10.141(2) _cell_angle_alpha 89.462(4) _cell_angle_beta 76.889(4) _cell_angle_gamma 80.215(4) _cell_volume 651.0(2) _cell_formula_units_Z 1 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1443 _cell_measurement_theta_min 0.00 _cell_measurement_theta_max 0.00 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.389 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 284 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9825 _exptl_absorpt_correction_T_max 0.9868 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '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 9011 _diffrn_reflns_av_R_equivalents 0.0297 _diffrn_reflns_av_sigmaI/netI 0.0454 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 30.51 _reflns_number_total 3789 _reflns_number_gt 2386 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0949P)^2^+0.0765P] 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 3789 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1022 _refine_ls_R_factor_gt 0.0648 _refine_ls_wR_factor_ref 0.1877 _refine_ls_wR_factor_gt 0.1606 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _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 0.07552(19) 0.5138(2) 0.45326(15) 0.0273(3) Uani 1 1 d . . . C2 C 0.0628(2) 0.6189(2) 0.34236(16) 0.0318(4) Uani 1 1 d . . . C3 C 0.2130(2) 0.6457(2) 0.25265(17) 0.0401(4) Uani 1 1 d . . . H3 H 0.2064 0.7169 0.1789 0.048 Uiso 1 1 calc R . . C4 C 0.3714(2) 0.5690(3) 0.27056(19) 0.0446(5) Uani 1 1 d . . . H4 H 0.4721 0.5881 0.2085 0.053 Uiso 1 1 calc R . . C5 C 0.3850(2) 0.4652(2) 0.37713(19) 0.0409(4) Uani 1 1 d . . . H5 H 0.4945 0.4130 0.3871 0.049 Uiso 1 1 calc R . . C6 C 0.2387(2) 0.4366(2) 0.47020(17) 0.0320(4) Uani 1 1 d . . . C7 C 0.2470(2) 0.3320(2) 0.58432(18) 0.0379(4) Uani 1 1 d . . . H7 H 0.3552 0.2798 0.5973 0.046 Uiso 1 1 calc R . . C8 C -0.1042(2) 0.6929(2) 0.32738(17) 0.0366(4) Uani 1 1 d . . . H8 H -0.1141 0.7616 0.2527 0.044 Uiso 1 1 calc R . . C9 C 0.05514(19) 0.05811(19) 0.00164(15) 0.0279(4) Uani 1 1 d . . . C10 C 0.2326(2) 0.0164(2) -0.05961(16) 0.0303(4) Uani 1 1 d . . . C11 C 0.3380(2) 0.1335(2) -0.05536(17) 0.0364(4) Uani 1 1 d . . . H11 H 0.4564 0.1078 -0.0970 0.044 Uiso 1 1 calc R . . C12 C 0.2713(2) 0.2859(2) 0.00885(18) 0.0379(4) Uani 1 1 d . . . H12 H 0.3450 0.3629 0.0126 0.045 Uiso 1 1 calc R . . C13 C 0.0982(2) 0.3285(2) 0.06797(17) 0.0364(4) Uani 1 1 d . . . H13 H 0.0548 0.4344 0.1109 0.044 Uiso 1 1 calc R . . C14 C -0.0124(2) 0.2172(2) 0.06485(15) 0.0302(4) Uani 1 1 d . . . C15 C -0.1931(2) 0.2554(2) 0.12493(16) 0.0351(4) Uani 1 1 d . . . H15 H -0.2400 0.3614 0.1667 0.042 Uiso 1 1 calc R . . C16 C 0.2967(2) -0.1450(2) -0.12330(17) 0.0348(4) Uani 1 1 d . . . H16 H 0.4148 -0.1740 -0.1650 0.042 Uiso 1 1 calc R . . C17 C 0.1545(5) 1.0737(5) 0.3482(4) 0.0385(8) Uani 0.50 1 d P . . C18 C 0.0591(4) 0.9949(4) 0.4714(3) 0.0344(7) Uani 0.50 1 d P . . C19 C 0.0398(3) 0.9194(2) 0.5915(2) 0.0527(6) Uani 1 1 d . . . C20 C 0.2333(5) 0.9168(5) 0.5291(3) 0.0350(8) Uani 0.50 1 d P . . N1 N 0.2600(2) 0.9890(2) 0.40758(18) 0.0512(5) Uani 1 1 d . . . O1 O 0.2736(4) 1.0528(5) 0.2950(3) 0.0672(9) Uani 0.50 1 d P . . O2 O 0.4369(3) 0.9868(4) 0.3505(3) 0.0504(7) Uani 0.50 1 d P . . O3 O 0.3458(4) 0.9093(5) 0.4641(4) 0.0656(9) Uani 0.50 1 d P . . 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 0.0277(8) 0.0283(8) 0.0256(7) -0.0044(6) -0.0054(6) -0.0045(6) C2 0.0381(9) 0.0304(9) 0.0274(8) -0.0018(6) -0.0072(7) -0.0076(7) C3 0.0490(11) 0.0429(11) 0.0281(8) 0.0011(7) -0.0029(7) -0.0147(9) C4 0.0384(10) 0.0546(13) 0.0379(10) -0.0071(9) 0.0044(8) -0.0176(9) C5 0.0297(9) 0.0474(11) 0.0432(10) -0.0099(8) -0.0036(7) -0.0052(8) C6 0.0291(8) 0.0331(9) 0.0332(8) -0.0074(7) -0.0075(7) -0.0027(7) C7 0.0361(9) 0.0368(10) 0.0419(10) -0.0024(8) -0.0170(8) 0.0020(7) C8 0.0457(10) 0.0338(9) 0.0329(9) 0.0043(7) -0.0159(7) -0.0044(8) C9 0.0318(8) 0.0287(8) 0.0231(7) 0.0042(6) -0.0089(6) -0.0018(6) C10 0.0309(8) 0.0325(9) 0.0271(8) 0.0050(6) -0.0087(6) -0.0017(7) C11 0.0317(9) 0.0441(11) 0.0342(9) 0.0072(8) -0.0088(7) -0.0077(7) C12 0.0430(10) 0.0383(10) 0.0365(9) 0.0061(7) -0.0119(8) -0.0152(8) C13 0.0477(10) 0.0310(9) 0.0315(9) 0.0016(7) -0.0121(7) -0.0057(8) C14 0.0364(9) 0.0293(9) 0.0247(7) 0.0033(6) -0.0096(6) -0.0020(7) C15 0.0385(9) 0.0315(9) 0.0309(8) -0.0012(7) -0.0068(7) 0.0042(7) C16 0.0311(9) 0.0376(10) 0.0321(8) 0.0023(7) -0.0061(7) 0.0025(7) C17 0.045(2) 0.040(2) 0.0294(17) 0.0015(15) -0.0081(16) -0.0036(17) C18 0.0295(16) 0.0349(18) 0.0356(18) -0.0049(15) -0.0048(13) -0.0001(15) C19 0.0837(16) 0.0353(10) 0.0338(10) -0.0036(8) -0.0100(10) 0.0005(10) C20 0.0333(19) 0.038(2) 0.0287(17) 0.0025(14) -0.0048(14) 0.0041(15) N1 0.0605(12) 0.0432(10) 0.0403(10) -0.0072(8) 0.0013(8) 0.0009(9) O1 0.0535(19) 0.080(2) 0.057(2) -0.0046(17) 0.0159(16) -0.0185(18) O2 0.0317(14) 0.069(2) 0.0435(15) 0.0003(14) 0.0054(11) -0.0073(13) O3 0.0345(17) 0.071(2) 0.088(3) -0.0173(19) -0.0194(18) 0.0089(16) _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 C6 1.420(2) . ? C1 C2 1.422(2) . ? C1 C1 1.424(3) 2_566 ? C2 C3 1.399(2) . ? C2 C8 1.435(2) . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? C4 C5 1.382(3) . ? C4 H4 0.9500 . ? C5 C6 1.397(2) . ? C5 H5 0.9500 . ? C6 C7 1.441(2) . ? C7 C8 1.343(3) 2_566 ? C7 H7 0.9500 . ? C8 C7 1.343(3) 2_566 ? C8 H8 0.9500 . ? C9 C9 1.423(3) 2 ? C9 C10 1.424(2) . ? C9 C14 1.424(2) . ? C10 C11 1.401(2) . ? C10 C16 1.439(2) . ? C11 C12 1.381(3) . ? C11 H11 0.9500 . ? C12 C13 1.388(3) . ? C12 H12 0.9500 . ? C13 C14 1.394(2) . ? C13 H13 0.9500 . ? C14 C15 1.443(2) . ? C15 C16 1.342(2) 2 ? C15 H15 0.9500 . ? C16 C15 1.342(2) 2 ? C16 H16 0.9500 . ? C17 O1 0.986(4) . ? C17 N1 1.269(4) . ? C17 C18 1.516(5) . ? C17 C19 1.556(5) 2_576 ? C18 C18 0.997(6) 2_576 ? C18 C19 1.259(4) 2_576 ? C18 C19 1.350(4) . ? C18 N1 1.612(4) . ? C18 C20 1.683(5) . ? C19 C18 1.259(4) 2_576 ? C19 C17 1.556(5) 2_576 ? C19 C20 1.558(4) . ? C20 O3 0.993(4) . ? C20 N1 1.350(4) . ? N1 O3 1.125(4) . ? N1 O1 1.241(4) . ? N1 O2 1.425(3) . ? O1 O2 1.573(5) . ? O2 O3 1.429(5) . ? 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 C6 C1 C2 119.88(15) . . ? C6 C1 C1 120.29(18) . 2_566 ? C2 C1 C1 119.83(18) . 2_566 ? C3 C2 C1 118.83(16) . . ? C3 C2 C8 122.83(16) . . ? C1 C2 C8 118.33(15) . . ? C4 C3 C2 120.53(17) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C5 C4 C3 121.07(17) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C4 C5 C6 120.38(17) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C5 C6 C1 119.30(16) . . ? C5 C6 C7 122.26(16) . . ? C1 C6 C7 118.44(15) . . ? C8 C7 C6 121.03(16) 2_566 . ? C8 C7 H7 119.5 2_566 . ? C6 C7 H7 119.5 . . ? C7 C8 C2 122.06(16) 2_566 . ? C7 C8 H8 119.0 2_566 . ? C2 C8 H8 119.0 . . ? C9 C9 C10 120.11(18) 2 . ? C9 C9 C14 119.98(18) 2 . ? C10 C9 C14 119.91(15) . . ? C11 C10 C9 118.89(15) . . ? C11 C10 C16 122.55(15) . . ? C9 C10 C16 118.56(15) . . ? C12 C11 C10 120.51(16) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 121.11(17) . . ? C11 C12 H12 119.4 . . ? C13 C12 H12 119.4 . . ? C12 C13 C14 120.56(17) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C9 118.99(15) . . ? C13 C14 C15 122.71(16) . . ? C9 C14 C15 118.29(15) . . ? C16 C15 C14 121.72(16) 2 . ? C16 C15 H15 119.1 2 . ? C14 C15 H15 119.1 . . ? C15 C16 C10 121.34(16) 2 . ? C15 C16 H16 119.3 2 . ? C10 C16 H16 119.3 . . ? O1 C17 N1 65.4(3) . . ? O1 C17 C18 133.6(4) . . ? N1 C17 C18 70.1(2) . . ? O1 C17 C19 167.4(4) . 2_576 ? N1 C17 C19 118.5(3) . 2_576 ? C18 C17 C19 48.37(19) . 2_576 ? C18 C18 C19 72.5(4) 2_576 2_576 ? C18 C18 C19 62.8(4) 2_576 . ? C19 C18 C19 135.2(3) 2_576 . ? C18 C18 C17 138.8(5) 2_576 . ? C19 C18 C17 67.5(2) 2_576 . ? C19 C18 C17 155.9(3) . . ? C18 C18 N1 168.1(5) 2_576 . ? C19 C18 N1 115.2(3) 2_576 . ? C19 C18 N1 109.0(2) . . ? C17 C18 N1 47.74(18) . . ? C18 C18 C20 122.6(5) 2_576 . ? C19 C18 C20 162.2(3) 2_576 . ? C19 C18 C20 60.7(2) . . ? C17 C18 C20 95.8(3) . . ? N1 C18 C20 48.34(17) . . ? C18 C19 C18 44.8(3) 2_576 . ? C18 C19 C17 64.2(2) 2_576 2_576 ? C18 C19 C17 108.4(2) . 2_576 ? C18 C19 C20 114.4(2) 2_576 . ? C18 C19 C20 70.3(2) . . ? C17 C19 C20 178.5(2) 2_576 . ? O3 C20 N1 54.8(3) . . ? O3 C20 C19 162.9(4) . . ? N1 C20 C19 112.1(3) . . ? O3 C20 C18 116.9(3) . . ? N1 C20 C18 63.10(19) . . ? C19 C20 C18 49.05(18) . . ? O3 N1 O1 137.3(3) . . ? O3 N1 C17 175.8(3) . . ? O1 N1 C17 46.3(2) . . ? O3 N1 C20 46.2(2) . . ? O1 N1 C20 175.5(3) . . ? C17 N1 C20 130.1(3) . . ? O3 N1 O2 67.0(3) . . ? O1 N1 O2 71.9(2) . . ? C17 N1 O2 117.0(3) . . ? C20 N1 O2 112.2(3) . . ? O3 N1 C18 113.9(3) . . ? O1 N1 C18 107.4(2) . . ? C17 N1 C18 62.2(2) . . ? C20 N1 C18 68.6(2) . . ? O2 N1 C18 179.0(2) . . ? C17 O1 N1 68.4(3) . . ? C17 O1 O2 126.3(4) . . ? N1 O1 O2 59.5(2) . . ? N1 O2 O3 46.42(15) . . ? N1 O2 O1 48.61(16) . . ? O3 O2 O1 94.4(2) . . ? C20 O3 N1 78.9(3) . . ? C20 O3 O2 143.3(4) . . ? N1 O3 O2 66.6(3) . . ? _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 29.40 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.581 _refine_diff_density_min -0.163 _refine_diff_density_rms 0.060