# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Andrew D. Smith' _publ_contact_author_email ads10@st-andrews.ac.uk loop_ _publ_author_name 'Craig D. Campbell' 'Chris. J. Collett' 'Jennifer E. Thomson' A.M.Z.Slawin 'Andrew D. Smith' data_10 _database_code_depnum_ccdc_archive 'CCDC 809724' #TrackingRef '10.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H14 N3 O.B F4 ' _chemical_formula_sum 'C12 H14 B F4 N3 O' _chemical_formula_weight 303.07 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 Iba2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'x+1, -y+1, z+1/2' '-x+1, y+1, z+1/2' _cell_length_a 10.628(4) _cell_length_b 34.498(9) _cell_length_c 7.374(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2703.5(16) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 1543 _cell_measurement_theta_min 1.92 _cell_measurement_theta_max 21.20 _exptl_crystal_description platelet _exptl_crystal_colour colourless _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.030 _exptl_crystal_size_min 0.010 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.489 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1248 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9118 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7878 _diffrn_reflns_av_R_equivalents 0.1295 _diffrn_reflns_av_sigmaI/netI 0.0833 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 41 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 25.34 _reflns_number_total 2227 _reflns_number_gt 1558 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0417P)^2^+1.3392P] 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 -1.5(13) _refine_ls_number_reflns 2227 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1024 _refine_ls_R_factor_gt 0.0586 _refine_ls_wR_factor_ref 0.1106 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.040 _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 0.3320(3) 0.13145(10) 0.0283(5) 0.0264(10) Uani 1 1 d . . . N2 N 0.2100(3) 0.14089(9) 0.0745(5) 0.0199(8) Uani 1 1 d . . . C3 C 0.1404(4) 0.10952(12) 0.1000(6) 0.0209(10) Uani 1 1 d . . . H3A H 0.0541 0.1088 0.1331 0.025 Uiso 1 1 calc R . . N3A N 0.2148(3) 0.07931(10) 0.0702(5) 0.0189(8) Uani 1 1 d . . . C4 C 0.2093(4) 0.03677(11) 0.0770(7) 0.0257(11) Uani 1 1 d . . . H4A H 0.1657 0.0259 -0.0304 0.031 Uiso 1 1 calc R . . H4B H 0.1673 0.0275 0.1887 0.031 Uiso 1 1 calc R . . C5 C 0.3506(4) 0.02675(12) 0.0765(7) 0.0281(11) Uani 1 1 d . . . H5A H 0.3805 0.0221 0.2017 0.034 Uiso 1 1 calc R . . H5B H 0.3660 0.0031 0.0036 0.034 Uiso 1 1 calc R . . C6 C 0.4199(4) 0.06160(12) -0.0070(7) 0.0269(12) Uani 1 1 d . . . H6A H 0.5016 0.0662 0.0536 0.032 Uiso 1 1 calc R . . H6B H 0.4339 0.0579 -0.1386 0.032 Uiso 1 1 calc R . . C1A C 0.3302(4) 0.09366(13) 0.0285(6) 0.0196(10) Uani 1 1 d . . . C7 C 0.1738(4) 0.18082(12) 0.0934(6) 0.0215(10) Uani 1 1 d . . . C8 C 0.2494(4) 0.20931(11) 0.0244(6) 0.0201(10) Uani 1 1 d . . . H8A H 0.3263 0.2028 -0.0338 0.024 Uiso 1 1 calc R . . C9 C 0.2135(4) 0.24774(13) 0.0398(6) 0.0208(10) Uani 1 1 d . . . H9A H 0.2653 0.2677 -0.0081 0.025 Uiso 1 1 calc R . . C10 C 0.1008(4) 0.25694(11) 0.1260(6) 0.0186(10) Uani 1 1 d . . . C11 C 0.0264(4) 0.22781(11) 0.1964(6) 0.0224(10) Uani 1 1 d . . . H11A H -0.0503 0.2342 0.2553 0.027 Uiso 1 1 calc R . . C12 C 0.0616(4) 0.18986(11) 0.1826(6) 0.0224(11) Uani 1 1 d . . . H12A H 0.0107 0.1699 0.2327 0.027 Uiso 1 1 calc R . . O10 O 0.0567(2) 0.29384(8) 0.1485(4) 0.0255(8) Uani 1 1 d . . . C13 C 0.1262(4) 0.32507(12) 0.0675(7) 0.0308(12) Uani 1 1 d . . . H13A H 0.2115 0.3256 0.1177 0.046 Uiso 1 1 calc R . . H13B H 0.0839 0.3497 0.0936 0.046 Uiso 1 1 calc R . . H13C H 0.1305 0.3212 -0.0640 0.046 Uiso 1 1 calc R . . B1 B 0.1898(5) 0.08038(15) 0.5660(8) 0.0246(13) Uani 1 1 d . . . F1 F 0.2812(2) 0.09403(8) 0.4488(4) 0.0425(8) Uani 1 1 d . . . F2 F 0.1464(2) 0.11024(6) 0.6753(3) 0.0285(7) Uani 1 1 d . . . F3 F 0.0888(2) 0.06618(7) 0.4629(4) 0.0363(7) Uani 1 1 d . . . F4 F 0.2382(3) 0.05114(8) 0.6704(4) 0.0523(9) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.016(2) 0.031(2) 0.033(3) -0.0015(18) 0.0043(19) 0.0034(16) N2 0.0159(19) 0.025(2) 0.018(2) 0.0021(18) 0.0001(18) -0.0007(16) C3 0.018(2) 0.024(2) 0.021(3) -0.003(2) -0.001(2) -0.002(2) N3A 0.0185(19) 0.023(2) 0.0151(19) 0.0022(17) 0.0009(18) -0.0020(16) C4 0.027(2) 0.020(2) 0.030(3) -0.003(2) -0.001(2) -0.0049(18) C5 0.027(2) 0.028(3) 0.029(3) -0.002(2) 0.000(3) 0.0040(19) C6 0.022(2) 0.030(3) 0.029(3) -0.005(2) 0.001(2) 0.003(2) C1A 0.018(2) 0.026(3) 0.015(3) 0.0032(19) 0.001(2) -0.0018(19) C7 0.018(2) 0.029(3) 0.017(3) -0.001(2) -0.005(2) -0.0019(19) C8 0.015(2) 0.029(3) 0.016(2) 0.001(2) -0.0008(19) -0.0024(19) C9 0.018(2) 0.023(2) 0.022(3) 0.002(2) -0.004(2) -0.0048(19) C10 0.018(2) 0.022(2) 0.015(3) -0.0023(19) -0.007(2) -0.0001(19) C11 0.016(2) 0.034(3) 0.018(3) -0.006(2) 0.004(2) 0.003(2) C12 0.021(2) 0.030(3) 0.017(3) -0.003(2) 0.002(2) -0.0055(19) O10 0.0211(17) 0.0224(16) 0.033(2) -0.0012(15) 0.0010(15) 0.0004(13) C13 0.021(2) 0.029(3) 0.042(3) 0.000(3) 0.002(3) 0.001(2) B1 0.020(3) 0.028(3) 0.026(3) 0.006(3) -0.007(3) 0.006(2) F1 0.0253(15) 0.072(2) 0.0306(17) -0.0047(16) 0.0066(15) -0.0093(14) F2 0.0231(13) 0.0308(14) 0.0317(17) -0.0057(14) -0.0029(14) 0.0038(11) F3 0.0232(15) 0.0492(17) 0.0365(16) -0.0131(15) -0.0008(14) -0.0029(13) F4 0.075(2) 0.0458(17) 0.036(2) 0.0018(15) -0.0100(18) 0.0275(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 N1 C1A 1.304(5) . ? N1 N2 1.381(5) . ? N2 C3 1.324(5) . ? N2 C7 1.437(5) . ? C3 N3A 1.327(5) . ? C3 H3A 0.9500 . ? N3A C1A 1.358(5) . ? N3A C4 1.469(5) . ? C4 C5 1.541(6) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.538(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C1A 1.483(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.367(6) . ? C7 C12 1.397(6) . ? C8 C9 1.385(6) . ? C8 H8A 0.9500 . ? C9 C10 1.392(6) . ? C9 H9A 0.9500 . ? C10 O10 1.367(5) . ? C10 C11 1.380(6) . ? C11 C12 1.365(5) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? O10 C13 1.436(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? B1 F4 1.369(6) . ? B1 F1 1.383(6) . ? B1 F2 1.387(6) . ? B1 F3 1.404(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 C1A N1 N2 102.8(3) . . ? C3 N2 N1 111.5(3) . . ? C3 N2 C7 128.4(4) . . ? N1 N2 C7 120.1(3) . . ? N3A C3 N2 106.6(4) . . ? N3A C3 H3A 126.7 . . ? N2 C3 H3A 126.7 . . ? C3 N3A C1A 106.8(4) . . ? C3 N3A C4 139.0(4) . . ? C1A N3A C4 114.1(3) . . ? N3A C4 C5 100.6(3) . . ? N3A C4 H4A 111.6 . . ? C5 C4 H4A 111.6 . . ? N3A C4 H4B 111.6 . . ? C5 C4 H4B 111.6 . . ? H4A C4 H4B 109.4 . . ? C6 C5 C4 107.0(3) . . ? C6 C5 H5A 110.3 . . ? C4 C5 H5A 110.3 . . ? C6 C5 H5B 110.3 . . ? C4 C5 H5B 110.3 . . ? H5A C5 H5B 108.6 . . ? C1A C6 C5 101.8(3) . . ? C1A C6 H6A 111.4 . . ? C5 C6 H6A 111.4 . . ? C1A C6 H6B 111.4 . . ? C5 C6 H6B 111.4 . . ? H6A C6 H6B 109.3 . . ? N1 C1A N3A 112.2(3) . . ? N1 C1A C6 137.4(4) . . ? N3A C1A C6 110.4(4) . . ? C8 C7 C12 121.1(4) . . ? C8 C7 N2 119.7(4) . . ? C12 C7 N2 119.2(4) . . ? C7 C8 C9 119.7(4) . . ? C7 C8 H8A 120.1 . . ? C9 C8 H8A 120.1 . . ? C8 C9 C10 119.5(4) . . ? C8 C9 H9A 120.2 . . ? C10 C9 H9A 120.2 . . ? O10 C10 C11 115.9(4) . . ? O10 C10 C9 124.2(4) . . ? C11 C10 C9 119.9(4) . . ? C12 C11 C10 120.9(4) . . ? C12 C11 H11A 119.6 . . ? C10 C11 H11A 119.6 . . ? C11 C12 C7 118.9(4) . . ? C11 C12 H12A 120.6 . . ? C7 C12 H12A 120.6 . . ? C10 O10 C13 118.2(3) . . ? O10 C13 H13A 109.5 . . ? O10 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O10 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? F4 B1 F1 109.8(4) . . ? F4 B1 F2 110.2(5) . . ? F1 B1 F2 110.1(4) . . ? F4 B1 F3 109.6(4) . . ? F1 B1 F3 108.5(4) . . ? F2 B1 F3 108.6(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 C1A N1 N2 C3 -0.2(5) . . . . ? C1A N1 N2 C7 178.4(4) . . . . ? N1 N2 C3 N3A -0.3(5) . . . . ? C7 N2 C3 N3A -178.8(4) . . . . ? N2 C3 N3A C1A 0.6(5) . . . . ? N2 C3 N3A C4 177.3(5) . . . . ? C3 N3A C4 C5 -163.6(5) . . . . ? C1A N3A C4 C5 13.0(5) . . . . ? N3A C4 C5 C6 -22.7(5) . . . . ? C4 C5 C6 C1A 24.2(5) . . . . ? N2 N1 C1A N3A 0.6(5) . . . . ? N2 N1 C1A C6 179.5(5) . . . . ? C3 N3A C1A N1 -0.8(5) . . . . ? C4 N3A C1A N1 -178.4(4) . . . . ? C3 N3A C1A C6 180.0(4) . . . . ? C4 N3A C1A C6 2.4(5) . . . . ? C5 C6 C1A N1 164.4(6) . . . . ? C5 C6 C1A N3A -16.6(5) . . . . ? C3 N2 C7 C8 -165.9(4) . . . . ? N1 N2 C7 C8 15.7(6) . . . . ? C3 N2 C7 C12 14.2(7) . . . . ? N1 N2 C7 C12 -164.2(4) . . . . ? C12 C7 C8 C9 -1.2(7) . . . . ? N2 C7 C8 C9 178.9(4) . . . . ? C7 C8 C9 C10 0.2(6) . . . . ? C8 C9 C10 O10 179.9(4) . . . . ? C8 C9 C10 C11 0.5(6) . . . . ? O10 C10 C11 C12 -179.6(4) . . . . ? C9 C10 C11 C12 -0.1(7) . . . . ? C10 C11 C12 C7 -0.9(7) . . . . ? C8 C7 C12 C11 1.6(7) . . . . ? N2 C7 C12 C11 -178.5(4) . . . . ? C11 C10 O10 C13 -176.0(4) . . . . ? C9 C10 O10 C13 4.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.203 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.058 # Attachment '2.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 809725' #TrackingRef '2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 N3,B F4' _chemical_formula_sum 'C11 H12 B F4 N3' _chemical_formula_weight 273.05 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' F F 0.0171 0.0103 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 6.7538(9) _cell_length_b 10.5562(15) _cell_length_c 17.047(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1215.3(3) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4617 _cell_measurement_theta_min 2.2692 _cell_measurement_theta_max 28.6226 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1500 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.492 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.133 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8943 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7908 _diffrn_reflns_av_R_equivalents 0.0233 _diffrn_reflns_av_sigmaI/netI 0.0253 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 25.33 _reflns_number_total 2196 _reflns_number_gt 2082 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0821P)^2^+0.2594P] 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 0.4(10) _refine_ls_number_reflns 2196 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1195 _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.046 _refine_ls_shift/su_mean 0.011 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 C1A C 0.5352(3) 0.0642(2) 0.15458(12) 0.0210(5) Uani 1 1 d . . . N1 N 0.5258(3) 0.18208(18) 0.13173(10) 0.0221(4) Uani 1 1 d . . . N2 N 0.5606(3) 0.17404(16) 0.05206(10) 0.0180(4) Uani 1 1 d . . . C3 C 0.5921(3) 0.0545(2) 0.02945(12) 0.0198(5) Uani 1 1 d . . . H3A H 0.6202 0.0258 -0.0222 0.024 Uiso 1 1 calc R . . N3A N 0.5762(3) -0.01608(17) 0.09362(10) 0.0203(4) Uani 1 1 d . . . C4 C 0.5847(4) -0.1505(2) 0.11659(14) 0.0274(5) Uani 1 1 d . . . H4A H 0.7010 -0.1936 0.0935 0.033 Uiso 1 1 calc R . . H4B H 0.4626 -0.1962 0.1014 0.033 Uiso 1 1 calc R . . C5 C 0.6033(4) -0.1386(2) 0.20645(14) 0.0330(6) Uani 1 1 d . . . H5A H 0.7441 -0.1412 0.2225 0.040 Uiso 1 1 calc R . . H5B H 0.5322 -0.2087 0.2328 0.040 Uiso 1 1 calc R . . C6 C 0.5092(4) -0.0089(2) 0.22864(13) 0.0285(5) Uani 1 1 d . . . H6A H 0.3675 -0.0181 0.2424 0.034 Uiso 1 1 calc R . . H6B H 0.5802 0.0314 0.2729 0.034 Uiso 1 1 calc R . . C7 C 0.5631(3) 0.28581(19) 0.00418(13) 0.0199(5) Uani 1 1 d . . . C8 C 0.5905(3) 0.4025(2) 0.03940(14) 0.0246(5) Uani 1 1 d . . . H8A H 0.6061 0.4089 0.0946 0.030 Uiso 1 1 calc R . . C9 C 0.5947(4) 0.5099(2) -0.00746(15) 0.0291(5) Uani 1 1 d . . . H9A H 0.6145 0.5908 0.0157 0.035 Uiso 1 1 calc R . . C10 C 0.5700(3) 0.4996(2) -0.08854(14) 0.0272(5) Uani 1 1 d . . . H10A H 0.5726 0.5733 -0.1205 0.033 Uiso 1 1 calc R . . C11 C 0.5418(3) 0.3821(2) -0.12225(14) 0.0252(5) Uani 1 1 d . . . H11A H 0.5249 0.3757 -0.1774 0.030 Uiso 1 1 calc R . . C12 C 0.5376(3) 0.2727(2) -0.07655(12) 0.0216(5) Uani 1 1 d . . . H12A H 0.5180 0.1918 -0.0997 0.026 Uiso 1 1 calc R . . B1 B 0.5413(4) -0.1355(2) -0.14184(15) 0.0245(5) Uani 1 1 d . . . F1 F 0.3523(3) -0.10941(19) -0.16676(11) 0.0582(5) Uani 1 1 d . . . F2 F 0.6494(3) -0.02321(16) -0.13977(9) 0.0501(5) Uani 1 1 d . . . F3 F 0.6285(3) -0.22082(14) -0.19321(8) 0.0433(4) Uani 1 1 d . . . F4 F 0.5305(3) -0.18721(14) -0.06699(8) 0.0412(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 C1A 0.0157(10) 0.0283(11) 0.0190(11) -0.0022(9) 0.0000(9) 0.0006(8) N1 0.0211(10) 0.0308(10) 0.0144(8) -0.0029(8) 0.0015(8) 0.0014(8) N2 0.0161(9) 0.0213(9) 0.0167(8) 0.0003(7) -0.0006(7) 0.0000(7) C3 0.0192(11) 0.0200(10) 0.0202(10) -0.0016(8) 0.0008(9) 0.0005(8) N3A 0.0199(9) 0.0226(9) 0.0183(9) 0.0009(7) 0.0007(8) -0.0004(8) C4 0.0356(13) 0.0209(11) 0.0257(12) 0.0045(9) 0.0007(11) 0.0013(10) C5 0.0424(14) 0.0345(13) 0.0222(12) 0.0084(10) 0.0033(11) 0.0048(12) C6 0.0301(12) 0.0367(13) 0.0188(11) 0.0038(10) -0.0012(10) 0.0014(11) C7 0.0153(11) 0.0201(11) 0.0243(11) 0.0023(9) -0.0003(9) 0.0016(9) C8 0.0224(12) 0.0248(11) 0.0267(12) -0.0038(9) -0.0026(9) 0.0011(9) C9 0.0244(12) 0.0221(11) 0.0409(13) -0.0035(10) 0.0001(11) 0.0003(10) C10 0.0208(11) 0.0254(12) 0.0355(13) 0.0063(10) 0.0001(10) 0.0030(9) C11 0.0178(11) 0.0312(12) 0.0267(12) 0.0063(9) 0.0030(10) 0.0007(10) C12 0.0183(11) 0.0248(11) 0.0217(11) -0.0003(9) 0.0010(9) 0.0006(9) B1 0.0318(13) 0.0204(12) 0.0212(12) -0.0007(10) 0.0023(11) -0.0007(11) F1 0.0458(10) 0.0701(13) 0.0587(11) 0.0084(10) -0.0082(9) 0.0138(9) F2 0.0749(12) 0.0391(9) 0.0363(8) -0.0109(7) 0.0220(8) -0.0274(9) F3 0.0685(10) 0.0309(8) 0.0305(8) -0.0056(6) 0.0084(8) 0.0089(8) F4 0.0690(11) 0.0317(8) 0.0230(7) 0.0035(6) 0.0012(8) -0.0049(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 C1A N1 1.306(3) . ? C1A N3A 1.369(3) . ? C1A C6 1.490(3) . ? N1 N2 1.381(2) . ? N2 C3 1.336(3) . ? N2 C7 1.435(3) . ? C3 N3A 1.328(3) . ? C3 H3A 0.9500 . ? N3A C4 1.473(3) . ? C4 C5 1.542(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.556(4) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.382(3) . ? C7 C12 1.394(3) . ? C8 C9 1.388(3) . ? C8 H8A 0.9500 . ? C9 C10 1.397(3) . ? C9 H9A 0.9500 . ? C10 C11 1.380(3) . ? C10 H10A 0.9500 . ? C11 C12 1.393(3) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? B1 F1 1.373(3) . ? B1 F3 1.387(3) . ? B1 F4 1.389(3) . ? B1 F2 1.393(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 C1A N3A 111.93(18) . . ? N1 C1A C6 137.8(2) . . ? N3A C1A C6 110.27(19) . . ? C1A N1 N2 103.09(17) . . ? C3 N2 N1 111.65(17) . . ? C3 N2 C7 127.62(17) . . ? N1 N2 C7 120.72(17) . . ? N3A C3 N2 106.23(18) . . ? N3A C3 H3A 126.9 . . ? N2 C3 H3A 126.9 . . ? C3 N3A C1A 107.10(18) . . ? C3 N3A C4 139.15(19) . . ? C1A N3A C4 113.72(18) . . ? N3A C4 C5 100.88(19) . . ? N3A C4 H4A 111.6 . . ? C5 C4 H4A 111.6 . . ? N3A C4 H4B 111.6 . . ? C5 C4 H4B 111.6 . . ? H4A C4 H4B 109.4 . . ? C4 C5 C6 106.25(19) . . ? C4 C5 H5A 110.5 . . ? C6 C5 H5A 110.5 . . ? C4 C5 H5B 110.5 . . ? C6 C5 H5B 110.5 . . ? H5A C5 H5B 108.7 . . ? C1A C6 C5 101.62(18) . . ? C1A C6 H6A 111.4 . . ? C5 C6 H6A 111.4 . . ? C1A C6 H6B 111.4 . . ? C5 C6 H6B 111.4 . . ? H6A C6 H6B 109.3 . . ? C8 C7 C12 122.3(2) . . ? C8 C7 N2 119.15(19) . . ? C12 C7 N2 118.60(18) . . ? C7 C8 C9 118.8(2) . . ? C7 C8 H8A 120.6 . . ? C9 C8 H8A 120.6 . . ? C8 C9 C10 120.2(2) . . ? C8 C9 H9A 119.9 . . ? C10 C9 H9A 119.9 . . ? C11 C10 C9 119.9(2) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C10 C11 C12 121.0(2) . . ? C10 C11 H11A 119.5 . . ? C12 C11 H11A 119.5 . . ? C11 C12 C7 117.9(2) . . ? C11 C12 H12A 121.1 . . ? C7 C12 H12A 121.1 . . ? F1 B1 F3 109.3(2) . . ? F1 B1 F4 108.3(2) . . ? F3 B1 F4 110.3(2) . . ? F1 B1 F2 108.9(2) . . ? F3 B1 F2 110.2(2) . . ? F4 B1 F2 109.8(2) . . ? 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 N3A C1A N1 N2 0.7(2) . . . . ? C6 C1A N1 N2 -177.4(2) . . . . ? C1A N1 N2 C3 -0.8(2) . . . . ? C1A N1 N2 C7 -179.87(18) . . . . ? N1 N2 C3 N3A 0.6(2) . . . . ? C7 N2 C3 N3A 179.59(19) . . . . ? N2 C3 N3A C1A -0.2(2) . . . . ? N2 C3 N3A C4 177.9(2) . . . . ? N1 C1A N3A C3 -0.4(2) . . . . ? C6 C1A N3A C3 178.30(18) . . . . ? N1 C1A N3A C4 -178.96(19) . . . . ? C6 C1A N3A C4 -0.3(3) . . . . ? C3 N3A C4 C5 166.0(3) . . . . ? C1A N3A C4 C5 -16.1(3) . . . . ? N3A C4 C5 C6 25.4(2) . . . . ? N1 C1A C6 C5 -165.4(3) . . . . ? N3A C1A C6 C5 16.4(2) . . . . ? C4 C5 C6 C1A -25.9(2) . . . . ? C3 N2 C7 C8 -159.4(2) . . . . ? N1 N2 C7 C8 19.5(3) . . . . ? C3 N2 C7 C12 20.6(3) . . . . ? N1 N2 C7 C12 -160.52(19) . . . . ? C12 C7 C8 C9 -0.7(3) . . . . ? N2 C7 C8 C9 179.3(2) . . . . ? C7 C8 C9 C10 0.5(3) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C9 C10 C11 C12 -0.1(3) . . . . ? C10 C11 C12 C7 -0.1(3) . . . . ? C8 C7 C12 C11 0.4(3) . . . . ? N2 C7 C12 C11 -179.57(19) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.628 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.053 # Attachment '9.cif' data_9 _database_code_depnum_ccdc_archive 'CCDC 809726' #TrackingRef '9.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_absolute_configuration unk _chemical_formula_moiety 'C11 H7 F5 N3,B F4' _chemical_formula_sum 'C11 H7 B F9 N3' _chemical_formula_weight 363.01 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' 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 8.2061(17) _cell_length_b 7.6948(16) _cell_length_c 10.792(2) _cell_angle_alpha 90.00 _cell_angle_beta 101.725(5) _cell_angle_gamma 90.00 _cell_volume 667.2(2) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2238 _cell_measurement_theta_min 1.9271 _cell_measurement_theta_max 28.4883 _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.1000 _exptl_crystal_size_mid 0.1000 _exptl_crystal_size_min 0.1000 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.807 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.198 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8056 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4345 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.33 _reflns_number_total 2050 _reflns_number_gt 1644 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0757P)^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 SHELXL _refine_ls_extinction_coef 0.018(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(12) _refine_ls_number_reflns 2050 _refine_ls_number_parameters 218 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0528 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1303 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 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 0.1843(4) 0.6191(5) 0.6469(3) 0.0356(9) Uani 1 1 d . . . N2 N 0.2510(4) 0.6853(5) 0.5491(3) 0.0299(8) Uani 1 1 d . . . C3 C 0.4082(5) 0.7312(6) 0.5859(4) 0.0361(11) Uani 1 1 d . . . H3A H 0.4797 0.7756 0.5343 0.043 Uiso 1 1 calc R . . N3A N 0.4460(4) 0.7028(6) 0.7097(3) 0.0332(8) Uani 1 1 d . . . C4 C 0.5889(5) 0.7190(8) 0.8160(4) 0.0394(11) Uani 1 1 d . . . H4A H 0.6102 0.8420 0.8411 0.047 Uiso 1 1 calc R . . H4B H 0.6907 0.6684 0.7948 0.047 Uiso 1 1 calc R . . C5 C 0.5335(6) 0.6183(10) 0.9169(5) 0.068(2) Uani 1 1 d . . . H5A H 0.5622 0.6821 0.9981 0.082 Uiso 1 1 calc R . . H5B H 0.5913 0.5046 0.9276 0.082 Uiso 1 1 calc R . . C6 C 0.3457(5) 0.5899(7) 0.8816(4) 0.0405(12) Uani 1 1 d . . . H6A H 0.3161 0.4681 0.8968 0.049 Uiso 1 1 calc R . . H6B H 0.2860 0.6687 0.9296 0.049 Uiso 1 1 calc R . . C1A C 0.3081(5) 0.6321(7) 0.7438(4) 0.0347(10) Uani 1 1 d . . . C7 C 0.1553(5) 0.6944(7) 0.4226(3) 0.0291(9) Uani 1 1 d . . . F8 F 0.1149(4) 0.3928(4) 0.4169(3) 0.0510(8) Uani 1 1 d . . . C8 C 0.0915(6) 0.5479(6) 0.3586(4) 0.0350(11) Uani 1 1 d . . . F9 F -0.0529(4) 0.4118(4) 0.1727(3) 0.0539(8) Uani 1 1 d . . . C9 C 0.0073(5) 0.5560(7) 0.2356(4) 0.0351(11) Uani 1 1 d . . . F10 F -0.0881(3) 0.7226(4) 0.0526(2) 0.0441(7) Uani 1 1 d . . . C10 C -0.0093(5) 0.7135(7) 0.1744(4) 0.0317(10) Uani 1 1 d . . . F11 F 0.0405(3) 1.0146(3) 0.1741(2) 0.0408(7) Uani 1 1 d . . . C11 C 0.0549(5) 0.8614(6) 0.2350(4) 0.0293(9) Uani 1 1 d . . . F12 F 0.2005(3) 0.9968(3) 0.4200(2) 0.0390(7) Uani 1 1 d . . . C12 C 0.1360(5) 0.8520(6) 0.3613(4) 0.0308(10) Uani 1 1 d . . . B1 B 0.5083(7) 0.6818(9) 0.2752(4) 0.0410(13) Uani 1 1 d . . . F1 F 0.4641(4) 0.5568(4) 0.3544(3) 0.0541(8) Uani 1 1 d . . . F2 F 0.3812(3) 0.6899(6) 0.1692(2) 0.0707(11) Uani 1 1 d . . . F3 F 0.6537(3) 0.6399(6) 0.2402(3) 0.0742(13) Uani 1 1 d . . . F4 F 0.5168(5) 0.8390(4) 0.3403(3) 0.0676(10) 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 0.0317(18) 0.047(2) 0.0274(18) 0.0048(18) 0.0032(16) -0.0033(17) N2 0.0309(19) 0.032(2) 0.0261(17) 0.0027(16) 0.0034(15) -0.0022(15) C3 0.035(2) 0.038(3) 0.035(2) 0.001(2) 0.006(2) -0.0030(19) N3A 0.0331(19) 0.035(2) 0.0302(17) 0.0036(17) 0.0039(15) -0.0007(16) C4 0.032(2) 0.050(3) 0.031(2) 0.004(2) -0.005(2) -0.001(2) C5 0.043(3) 0.116(6) 0.039(3) 0.002(3) -0.005(2) -0.031(3) C6 0.039(2) 0.052(3) 0.029(2) 0.006(2) 0.004(2) -0.002(2) C1A 0.034(2) 0.038(3) 0.032(2) 0.002(2) 0.006(2) -0.002(2) C7 0.031(2) 0.033(2) 0.0222(19) 0.000(2) 0.0022(18) 0.0005(18) F8 0.070(2) 0.0335(17) 0.0457(16) 0.0026(14) 0.0020(14) -0.0102(14) C8 0.042(2) 0.030(3) 0.032(2) 0.004(2) 0.006(2) -0.002(2) F9 0.070(2) 0.0412(18) 0.0447(15) -0.0124(14) -0.0011(15) -0.0133(16) C9 0.038(2) 0.035(3) 0.032(2) -0.008(2) 0.007(2) -0.013(2) F10 0.0429(14) 0.061(2) 0.0262(12) -0.0019(14) 0.0018(11) -0.0059(13) C10 0.029(2) 0.046(3) 0.0179(18) 0.002(2) -0.0006(17) -0.005(2) F11 0.0397(14) 0.0401(17) 0.0392(15) 0.0094(13) -0.0002(12) 0.0005(12) C11 0.030(2) 0.032(3) 0.026(2) 0.007(2) 0.0060(17) 0.0016(18) F12 0.0433(14) 0.0280(15) 0.0404(15) -0.0021(12) -0.0043(12) -0.0019(12) C12 0.030(2) 0.028(2) 0.033(2) -0.002(2) 0.0027(18) 0.0016(18) B1 0.044(3) 0.056(4) 0.026(2) 0.007(3) 0.013(2) 0.004(3) F1 0.082(2) 0.0374(18) 0.0496(16) 0.0049(15) 0.0283(15) 0.0024(15) F2 0.0501(18) 0.130(3) 0.0323(14) 0.012(2) 0.0093(13) 0.023(2) F3 0.0324(14) 0.144(4) 0.0476(16) -0.006(2) 0.0115(13) 0.0111(19) F4 0.104(3) 0.046(2) 0.065(2) -0.0040(17) 0.0455(19) -0.0201(19) _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 C1A 1.305(5) . ? N1 N2 1.381(5) . ? N2 C3 1.318(5) . ? N2 C7 1.433(5) . ? C3 N3A 1.327(6) . ? C3 H3A 0.9500 . ? N3A C1A 1.371(6) . ? N3A C4 1.470(5) . ? C4 C5 1.481(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.526(6) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C6 C1A 1.492(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.369(7) . ? C7 C12 1.375(7) . ? F8 C8 1.345(6) . ? C8 C9 1.367(6) . ? F9 C9 1.342(5) . ? C9 C10 1.374(7) . ? F10 C10 1.344(4) . ? C10 C11 1.363(6) . ? F11 C11 1.343(5) . ? C11 C12 1.392(6) . ? F12 C12 1.337(5) . ? B1 F3 1.361(6) . ? B1 F2 1.384(5) . ? B1 F1 1.384(6) . ? B1 F4 1.394(7) . ? 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 C1A N1 N2 102.6(3) . . ? C3 N2 N1 112.6(3) . . ? C3 N2 C7 126.0(4) . . ? N1 N2 C7 121.4(3) . . ? N2 C3 N3A 105.8(4) . . ? N2 C3 H3A 127.1 . . ? N3A C3 H3A 127.1 . . ? C3 N3A C1A 107.4(4) . . ? C3 N3A C4 139.3(4) . . ? C1A N3A C4 113.3(4) . . ? N3A C4 C5 102.4(4) . . ? N3A C4 H4A 111.3 . . ? C5 C4 H4A 111.3 . . ? N3A C4 H4B 111.3 . . ? C5 C4 H4B 111.3 . . ? H4A C4 H4B 109.2 . . ? C4 C5 C6 109.7(4) . . ? C4 C5 H5A 109.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5B 109.7 . . ? C6 C5 H5B 109.7 . . ? H5A C5 H5B 108.2 . . ? C1A C6 C5 102.2(4) . . ? C1A C6 H6A 111.3 . . ? C5 C6 H6A 111.3 . . ? C1A C6 H6B 111.3 . . ? C5 C6 H6B 111.3 . . ? H6A C6 H6B 109.2 . . ? N1 C1A N3A 111.5(4) . . ? N1 C1A C6 138.7(4) . . ? N3A C1A C6 109.8(3) . . ? C8 C7 C12 119.2(3) . . ? C8 C7 N2 121.4(4) . . ? C12 C7 N2 119.3(4) . . ? F8 C8 C9 119.4(4) . . ? F8 C8 C7 119.4(4) . . ? C9 C8 C7 121.2(4) . . ? F9 C9 C8 121.0(4) . . ? F9 C9 C10 119.7(4) . . ? C8 C9 C10 119.2(4) . . ? F10 C10 C11 119.2(4) . . ? F10 C10 C9 119.8(4) . . ? C11 C10 C9 121.0(3) . . ? F11 C11 C10 120.7(4) . . ? F11 C11 C12 120.1(4) . . ? C10 C11 C12 119.2(4) . . ? F12 C12 C7 120.7(4) . . ? F12 C12 C11 119.1(4) . . ? C7 C12 C11 120.1(4) . . ? F3 B1 F2 109.7(4) . . ? F3 B1 F1 111.2(5) . . ? F2 B1 F1 107.1(4) . . ? F3 B1 F4 112.9(5) . . ? F2 B1 F4 109.3(5) . . ? F1 B1 F4 106.5(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C1A N1 N2 C3 1.5(5) . . . . ? C1A N1 N2 C7 179.6(4) . . . . ? N1 N2 C3 N3A -2.5(6) . . . . ? C7 N2 C3 N3A 179.6(5) . . . . ? N2 C3 N3A C1A 2.4(6) . . . . ? N2 C3 N3A C4 179.8(6) . . . . ? C3 N3A C4 C5 -166.9(7) . . . . ? C1A N3A C4 C5 10.5(6) . . . . ? N3A C4 C5 C6 -16.1(7) . . . . ? C4 C5 C6 C1A 15.8(7) . . . . ? N2 N1 C1A N3A 0.1(5) . . . . ? N2 N1 C1A C6 -178.6(6) . . . . ? C3 N3A C1A N1 -1.6(6) . . . . ? C4 N3A C1A N1 -179.7(5) . . . . ? C3 N3A C1A C6 177.5(4) . . . . ? C4 N3A C1A C6 -0.7(6) . . . . ? C5 C6 C1A N1 169.5(7) . . . . ? C5 C6 C1A N3A -9.1(6) . . . . ? C3 N2 C7 C8 117.3(5) . . . . ? N1 N2 C7 C8 -60.5(6) . . . . ? C3 N2 C7 C12 -58.5(6) . . . . ? N1 N2 C7 C12 123.7(5) . . . . ? C12 C7 C8 F8 177.8(4) . . . . ? N2 C7 C8 F8 2.1(6) . . . . ? C12 C7 C8 C9 -0.9(7) . . . . ? N2 C7 C8 C9 -176.7(4) . . . . ? F8 C8 C9 F9 0.3(7) . . . . ? C7 C8 C9 F9 179.1(4) . . . . ? F8 C8 C9 C10 -176.9(4) . . . . ? C7 C8 C9 C10 1.8(7) . . . . ? F9 C9 C10 F10 1.0(6) . . . . ? C8 C9 C10 F10 178.3(4) . . . . ? F9 C9 C10 C11 -178.1(4) . . . . ? C8 C9 C10 C11 -0.8(7) . . . . ? F10 C10 C11 F11 -0.2(6) . . . . ? C9 C10 C11 F11 179.0(4) . . . . ? F10 C10 C11 C12 179.8(4) . . . . ? C9 C10 C11 C12 -1.1(7) . . . . ? C8 C7 C12 F12 -178.2(4) . . . . ? N2 C7 C12 F12 -2.4(6) . . . . ? C8 C7 C12 C11 -1.0(6) . . . . ? N2 C7 C12 C11 174.8(4) . . . . ? F11 C11 C12 F12 -0.8(6) . . . . ? C10 C11 C12 F12 179.3(4) . . . . ? F11 C11 C12 C7 -178.0(4) . . . . ? C10 C11 C12 C7 2.0(7) . . . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.394 _refine_diff_density_min -0.334 _refine_diff_density_rms 0.070