# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email jiao421@mail.ahnu.edu.cn _publ_contact_author_name 'Lijuan Jiao' loop_ _publ_author_name 'Weidong Pang' 'Xian-Fu Zhang' 'Jinyuan Zhou' 'Changjiang Yu' 'Erhong Hao' 'Lijuan Jiao' data_110228a_0m _database_code_depnum_ccdc_archive 'CCDC 867740' #TrackingRef '- 2a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H18 B2 F4 N4 O' _chemical_formula_weight 488.05 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' B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'C2/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.151(11) _cell_length_b 7.492(4) _cell_length_c 28.471(15) _cell_angle_alpha 90.00 _cell_angle_beta 99.012(6) _cell_angle_gamma 90.00 _cell_volume 4456(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2725 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 21.26 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2000 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9745 _exptl_absorpt_correction_T_max 0.9800 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 18201 _diffrn_reflns_av_R_equivalents 0.0958 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.68 _reflns_number_total 5186 _reflns_number_gt 2293 _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^)+(0.1500P)^2^+0.0100P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5186 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1969 _refine_ls_R_factor_gt 0.0903 _refine_ls_wR_factor_ref 0.3084 _refine_ls_wR_factor_gt 0.2566 _refine_ls_goodness_of_fit_ref 1.088 _refine_ls_restrained_S_all 1.088 _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 B1 B 0.3397(3) 0.4222(9) 0.0597(2) 0.0581(17) Uani 1 1 d . . . C1 C 0.4282(3) 0.3252(8) 0.1244(2) 0.0641(15) Uani 1 1 d . . . H1 H 0.4573 0.3008 0.1039 0.077 Uiso 1 1 calc R . . F1 F 0.37405(17) 0.5389(5) 0.03685(11) 0.0832(11) Uani 1 1 d . . . N1 N 0.3708(2) 0.3924(5) 0.11086(13) 0.0491(10) Uani 1 1 d . . . O1 O 0.4602(2) 0.5979(7) 0.42876(15) 0.0965(15) Uani 1 1 d . . . B2 B 0.1053(3) 0.3942(8) 0.2457(2) 0.0540(15) Uani 1 1 d . . . C2 C 0.4399(3) 0.2950(8) 0.1735(2) 0.0617(15) Uani 1 1 d . . . H2 H 0.4770 0.2500 0.1914 0.074 Uiso 1 1 calc R . . F2 F 0.33410(18) 0.2614(5) 0.03565(11) 0.0873(11) Uani 1 1 d . . . N2 N 0.2733(2) 0.4967(5) 0.06194(14) 0.0541(11) Uani 1 1 d . . . C3 C 0.3846(2) 0.3465(7) 0.18941(18) 0.0549(13) Uani 1 1 d . . . H3 H 0.3769 0.3398 0.2207 0.066 Uiso 1 1 calc R . . F3 F 0.07834(14) 0.2392(4) 0.22585(11) 0.0719(9) Uani 1 1 d . . . N3 N 0.17085(18) 0.4238(5) 0.23215(13) 0.0473(10) Uani 1 1 d . . . C4 C 0.3419(2) 0.4105(6) 0.15084(16) 0.0463(12) Uani 1 1 d . . . F4 F 0.06575(15) 0.5360(5) 0.22959(11) 0.0752(10) Uani 1 1 d . . . N4 N 0.11494(19) 0.3827(5) 0.29985(14) 0.0504(10) Uani 1 1 d . . . C5 C 0.2796(2) 0.4741(6) 0.14698(16) 0.0453(12) Uani 1 1 d . . . C6 C 0.2466(3) 0.5239(6) 0.10243(16) 0.0495(12) Uani 1 1 d . . . C7 C 0.1870(3) 0.6033(7) 0.08904(19) 0.0576(14) Uani 1 1 d . . . H7 H 0.1586 0.6361 0.1094 0.069 Uiso 1 1 calc R . . C8 C 0.1773(3) 0.6248(8) 0.0406(2) 0.0694(16) Uani 1 1 d . . . H8 H 0.1416 0.6743 0.0219 0.083 Uiso 1 1 calc R . . C9 C 0.2309(3) 0.5583(8) 0.02537(19) 0.0663(16) Uani 1 1 d . . . H9 H 0.2372 0.5560 -0.0062 0.080 Uiso 1 1 calc R . . C10 C 0.1845(2) 0.4285(6) 0.18826(17) 0.0488(12) Uani 1 1 d . . . H10 H 0.1555 0.4018 0.1611 0.059 Uiso 1 1 calc R . . C11 C 0.2474(2) 0.4781(6) 0.18809(16) 0.0414(11) Uani 1 1 d . . . C12 C 0.2727(2) 0.5086(6) 0.23617(16) 0.0456(12) Uani 1 1 d . . . H12 H 0.3140 0.5472 0.2478 0.055 Uiso 1 1 calc R . . C13 C 0.2255(2) 0.4710(6) 0.26282(15) 0.0409(11) Uani 1 1 d . . . C14 C 0.2269(2) 0.4628(6) 0.31262(16) 0.0425(11) Uani 1 1 d . . . C15 C 0.1719(2) 0.4155(6) 0.33013(17) 0.0432(11) Uani 1 1 d . . . C16 C 0.1607(3) 0.3776(7) 0.37680(18) 0.0555(13) Uani 1 1 d . . . H16 H 0.1906 0.3845 0.4044 0.067 Uiso 1 1 calc R . . C17 C 0.0985(3) 0.3295(7) 0.3739(2) 0.0591(14) Uani 1 1 d . . . H17 H 0.0774 0.3020 0.3992 0.071 Uiso 1 1 calc R . . C18 C 0.0722(3) 0.3290(7) 0.3260(2) 0.0610(14) Uani 1 1 d . . . H18 H 0.0304 0.2955 0.3141 0.073 Uiso 1 1 calc R . . C19 C 0.2865(2) 0.4943(6) 0.34496(16) 0.0431(11) Uani 1 1 d . . . C20 C 0.2888(2) 0.5889(6) 0.38674(15) 0.0471(12) Uani 1 1 d . . . H20 H 0.2507 0.6295 0.3953 0.057 Uiso 1 1 calc R . . C21 C 0.3453(3) 0.6255(7) 0.41619(17) 0.0566(14) Uani 1 1 d . . . H21 H 0.3452 0.6892 0.4442 0.068 Uiso 1 1 calc R . . C22 C 0.4013(3) 0.5674(9) 0.4039(2) 0.0678(16) Uani 1 1 d . . . C23 C 0.4000(3) 0.4674(8) 0.36254(19) 0.0645(15) Uani 1 1 d . . . H23 H 0.4381 0.4248 0.3543 0.077 Uiso 1 1 calc R . . C24 C 0.3438(2) 0.4313(7) 0.33406(17) 0.0524(13) Uani 1 1 d . . . H24 H 0.3439 0.3631 0.3068 0.063 Uiso 1 1 calc R . . C25 C 0.4649(3) 0.7100(12) 0.4689(2) 0.101(2) Uani 1 1 d . . . H25A H 0.4477 0.8253 0.4595 0.151 Uiso 1 1 calc R . . H25B H 0.5091 0.7221 0.4829 0.151 Uiso 1 1 calc R . . H25C H 0.4413 0.6589 0.4918 0.151 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 B1 0.073(5) 0.055(4) 0.050(3) -0.003(3) 0.018(3) -0.009(3) C1 0.046(3) 0.074(4) 0.074(4) 0.000(3) 0.014(3) 0.002(3) F1 0.092(3) 0.097(3) 0.065(2) 0.0200(18) 0.0254(19) -0.010(2) N1 0.054(3) 0.047(2) 0.048(2) 0.0030(19) 0.014(2) -0.003(2) O1 0.066(3) 0.150(5) 0.069(3) -0.005(3) -0.005(2) -0.013(3) B2 0.046(3) 0.055(4) 0.061(4) -0.007(3) 0.006(3) 0.013(3) C2 0.046(3) 0.068(4) 0.071(4) 0.011(3) 0.007(3) 0.005(3) F2 0.113(3) 0.076(2) 0.071(2) -0.0255(18) 0.008(2) 0.005(2) N2 0.068(3) 0.049(3) 0.044(2) 0.0008(19) 0.005(2) -0.008(2) C3 0.055(3) 0.056(3) 0.051(3) 0.008(2) 0.001(3) -0.002(3) F3 0.0578(19) 0.082(2) 0.078(2) -0.0249(18) 0.0162(16) -0.0176(16) N3 0.050(2) 0.045(2) 0.047(2) -0.0039(18) 0.009(2) 0.0020(18) C4 0.056(3) 0.036(3) 0.047(3) 0.000(2) 0.010(2) -0.008(2) F4 0.065(2) 0.090(2) 0.069(2) 0.0070(18) 0.0078(16) 0.0274(18) N4 0.046(2) 0.047(2) 0.059(3) 0.001(2) 0.012(2) 0.0038(19) C5 0.060(3) 0.031(2) 0.044(3) -0.001(2) 0.007(2) -0.008(2) C6 0.070(3) 0.038(3) 0.041(3) -0.003(2) 0.007(2) -0.005(2) C7 0.066(4) 0.049(3) 0.056(3) 0.005(2) 0.003(3) 0.001(3) C8 0.073(4) 0.065(4) 0.065(4) 0.010(3) -0.004(3) 0.006(3) C9 0.074(4) 0.071(4) 0.049(3) 0.009(3) -0.006(3) -0.008(3) C10 0.054(3) 0.045(3) 0.047(3) -0.002(2) 0.005(2) 0.003(2) C11 0.043(3) 0.035(2) 0.045(3) 0.002(2) 0.004(2) 0.004(2) C12 0.056(3) 0.035(3) 0.045(3) 0.002(2) 0.006(2) 0.003(2) C13 0.045(3) 0.034(2) 0.043(3) -0.002(2) 0.005(2) 0.003(2) C14 0.046(3) 0.035(2) 0.048(3) -0.002(2) 0.009(2) 0.002(2) C15 0.044(3) 0.036(3) 0.050(3) -0.002(2) 0.010(2) 0.002(2) C16 0.062(4) 0.050(3) 0.055(3) 0.003(2) 0.011(3) 0.007(3) C17 0.051(3) 0.062(3) 0.067(4) 0.009(3) 0.019(3) 0.011(3) C18 0.059(3) 0.055(3) 0.071(4) 0.003(3) 0.018(3) 0.007(3) C19 0.049(3) 0.034(3) 0.048(3) 0.004(2) 0.014(2) 0.007(2) C20 0.056(3) 0.041(3) 0.045(3) 0.004(2) 0.010(2) 0.004(2) C21 0.069(4) 0.059(3) 0.042(3) 0.003(2) 0.009(3) -0.007(3) C22 0.058(4) 0.088(5) 0.056(3) 0.008(3) 0.006(3) -0.004(3) C23 0.052(3) 0.084(4) 0.060(3) 0.010(3) 0.016(3) 0.014(3) C24 0.051(3) 0.058(3) 0.048(3) 0.004(2) 0.008(2) 0.006(2) C25 0.073(5) 0.145(7) 0.080(5) -0.017(5) -0.004(4) -0.025(4) _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 B1 F1 1.365(7) . ? B1 F2 1.382(7) . ? B1 N1 1.517(7) . ? B1 N2 1.522(8) . ? C1 N1 1.314(6) . ? C1 C2 1.399(7) . ? N1 C4 1.381(6) . ? O1 C22 1.352(6) . ? O1 C25 1.410(8) . ? B2 F3 1.376(7) . ? B2 F4 1.385(6) . ? B2 N3 1.513(7) . ? B2 N4 1.525(7) . ? C2 C3 1.376(7) . ? N2 C9 1.345(6) . ? N2 C6 1.377(6) . ? C3 C4 1.393(6) . ? N3 C10 1.326(6) . ? N3 C13 1.381(5) . ? C4 C5 1.389(7) . ? N4 C18 1.321(6) . ? N4 C15 1.390(6) . ? C5 C6 1.399(6) . ? C5 C11 1.444(7) . ? C6 C7 1.393(7) . ? C7 C8 1.372(7) . ? C8 C9 1.371(8) . ? C10 C11 1.382(7) . ? C11 C12 1.408(6) . ? C12 C13 1.374(6) . ? C13 C14 1.415(6) . ? C14 C15 1.381(6) . ? C14 C19 1.459(6) . ? C15 C16 1.415(7) . ? C16 C17 1.353(7) . ? C17 C18 1.389(7) . ? C19 C20 1.379(6) . ? C19 C24 1.380(7) . ? C20 C21 1.375(7) . ? C21 C22 1.359(8) . ? C22 C23 1.391(8) . ? C23 C24 1.358(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 F1 B1 F2 109.4(5) . . ? F1 B1 N1 111.7(5) . . ? F2 B1 N1 109.8(5) . . ? F1 B1 N2 110.4(5) . . ? F2 B1 N2 109.4(5) . . ? N1 B1 N2 106.2(4) . . ? N1 C1 C2 111.5(5) . . ? C1 N1 C4 107.7(4) . . ? C1 N1 B1 125.4(5) . . ? C4 N1 B1 126.5(4) . . ? C22 O1 C25 118.0(5) . . ? F3 B2 F4 108.7(4) . . ? F3 B2 N3 110.8(4) . . ? F4 B2 N3 109.4(5) . . ? F3 B2 N4 110.4(5) . . ? F4 B2 N4 110.9(4) . . ? N3 B2 N4 106.5(4) . . ? C3 C2 C1 104.9(5) . . ? C9 N2 C6 106.6(5) . . ? C9 N2 B1 127.0(5) . . ? C6 N2 B1 126.3(4) . . ? C2 C3 C4 108.5(5) . . ? C10 N3 C13 107.8(4) . . ? C10 N3 B2 126.0(4) . . ? C13 N3 B2 125.8(4) . . ? N1 C4 C5 120.4(4) . . ? N1 C4 C3 107.4(4) . . ? C5 C4 C3 132.1(5) . . ? C18 N4 C15 107.9(4) . . ? C18 N4 B2 126.3(5) . . ? C15 N4 B2 125.6(4) . . ? C4 C5 C6 119.7(5) . . ? C4 C5 C11 120.3(4) . . ? C6 C5 C11 119.8(5) . . ? N2 C6 C7 107.9(4) . . ? N2 C6 C5 120.5(5) . . ? C7 C6 C5 131.6(5) . . ? C8 C7 C6 108.2(5) . . ? C9 C8 C7 105.9(5) . . ? N2 C9 C8 111.4(5) . . ? N3 C10 C11 111.2(4) . . ? C10 C11 C12 105.1(4) . . ? C10 C11 C5 125.0(4) . . ? C12 C11 C5 129.5(4) . . ? C13 C12 C11 107.8(4) . . ? C12 C13 N3 108.2(4) . . ? C12 C13 C14 131.2(4) . . ? N3 C13 C14 120.4(4) . . ? C15 C14 C13 119.1(4) . . ? C15 C14 C19 120.5(4) . . ? C13 C14 C19 120.4(4) . . ? C14 C15 N4 121.3(4) . . ? C14 C15 C16 131.7(5) . . ? N4 C15 C16 106.9(4) . . ? C17 C16 C15 107.5(5) . . ? C16 C17 C18 107.3(5) . . ? N4 C18 C17 110.3(5) . . ? C20 C19 C24 117.1(5) . . ? C20 C19 C14 122.5(4) . . ? C24 C19 C14 120.3(4) . . ? C21 C20 C19 122.6(5) . . ? C22 C21 C20 119.2(5) . . ? O1 C22 C21 125.4(6) . . ? O1 C22 C23 115.4(5) . . ? C21 C22 C23 119.3(5) . . ? C24 C23 C22 120.7(5) . . ? C23 C24 C19 121.0(5) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.68 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.317 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.069 # Attachment '- 2b.cif' data_jlj-3 _database_code_depnum_ccdc_archive 'CCDC 867741' #TrackingRef '- 2b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H26 B2 F4 N4 O' _chemical_formula_weight 544.16 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.7354(3) _cell_length_b 14.3655(3) _cell_length_c 13.8591(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.259(2) _cell_angle_gamma 90.00 _cell_volume 2690.90(10) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 4175 _cell_measurement_theta_min 3.0737 _cell_measurement_theta_max 67.4564 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1128 _exptl_absorpt_coefficient_mu 0.847 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7617 _exptl_absorpt_correction_T_max 0.8099 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Enhance Ultra (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 15.9149 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10133 _diffrn_reflns_av_R_equivalents 0.0213 _diffrn_reflns_av_sigmaI/netI 0.0291 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 4.18 _diffrn_reflns_theta_max 67.54 _reflns_number_total 4752 _reflns_number_gt 3736 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_cell_refinement 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_data_reduction 'CrysAlisPro (Oxford Diffraction Ltd.)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 (L. J. Farrugia, 2001)' _computing_publication_material SHELXL-97 _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^)+(0.0604P)^2^+0.3570P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4752 _refine_ls_number_parameters 366 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0556 _refine_ls_R_factor_gt 0.0424 _refine_ls_wR_factor_ref 0.1218 _refine_ls_wR_factor_gt 0.1094 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group F1 F 1.27495(9) 0.48527(8) 0.70483(9) 0.0667(3) Uani 1 1 d . . . F2 F 1.23894(8) 0.47429(8) 0.54015(9) 0.0669(3) Uani 1 1 d . . . F4 F 0.78247(9) 0.03147(8) 0.68517(10) 0.0723(4) Uani 1 1 d . . . N1 N 1.39142(11) 0.40666(10) 0.62403(11) 0.0506(4) Uani 1 1 d . . . O1 O 1.57283(10) -0.06386(10) 0.87657(13) 0.0751(5) Uani 1 1 d . . . F3 F 0.72945(8) 0.17534(9) 0.63399(9) 0.0710(3) Uani 1 1 d . . . N4 N 0.86816(10) 0.11131(11) 0.57282(11) 0.0503(4) Uani 1 1 d . . . N3 N 0.88447(11) 0.16249(11) 0.74554(11) 0.0493(4) Uani 1 1 d . . . N2 N 1.23072(10) 0.33480(10) 0.63544(11) 0.0456(3) Uani 1 1 d . . . C3 C 1.41461(13) 0.13534(13) 0.82031(14) 0.0525(4) Uani 1 1 d . . . H3 H 1.3684 0.1673 0.8492 0.063 Uiso 1 1 calc R . . C4 C 1.43437(12) 0.16508(12) 0.72993(14) 0.0474(4) Uani 1 1 d . . . C16 C 1.01891(12) 0.18451(12) 0.65541(13) 0.0451(4) Uani 1 1 d . . . C23 C 0.96238(12) 0.14764(13) 0.57078(13) 0.0470(4) Uani 1 1 d . . . C14 C 1.11752(12) 0.22580(13) 0.65313(13) 0.0465(4) Uani 1 1 d . . . C21 C 0.86473(15) 0.18181(15) 0.83500(15) 0.0602(5) Uani 1 1 d . . . C7 C 1.38454(12) 0.24923(12) 0.68426(12) 0.0444(4) Uani 1 1 d . . . C17 C 0.98262(12) 0.18822(13) 0.74359(13) 0.0483(4) Uani 1 1 d . . . C8 C 1.43864(13) 0.32421(12) 0.65826(13) 0.0461(4) Uani 1 1 d . . . C11 C 1.46099(15) 0.46711(15) 0.60872(18) 0.0660(6) Uani 1 1 d . . . H11 H 1.4489 0.5278 0.5865 0.079 Uiso 1 1 calc R . . C6 C 1.54993(14) 0.03778(14) 0.73395(17) 0.0625(5) Uani 1 1 d . . . H6 H 1.5945 0.0043 0.7043 0.075 Uiso 1 1 calc R . . C9 C 1.54119(14) 0.33750(14) 0.66204(15) 0.0561(5) Uani 1 1 d . . . H9 H 1.5907 0.2939 0.6821 0.067 Uiso 1 1 calc R . . C13 C 1.20992(12) 0.18606(12) 0.68129(13) 0.0469(4) Uani 1 1 d . . . H13 H 1.2229 0.1254 0.7034 0.056 Uiso 1 1 calc R . . C18 C 1.02464(15) 0.22126(16) 0.83826(15) 0.0613(5) Uani 1 1 d . . . C1 C 1.53015(13) 0.01070(13) 0.82419(16) 0.0572(5) Uani 1 1 d . . . C12 C 1.28056(12) 0.25406(12) 0.67033(13) 0.0446(4) Uani 1 1 d . . . C15 C 1.13339(12) 0.31691(12) 0.62537(13) 0.0479(4) Uani 1 1 d . . . H15 H 1.0835 0.3595 0.6030 0.057 Uiso 1 1 calc R . . B1 B 1.28134(16) 0.42974(14) 0.62438(16) 0.0488(5) Uani 1 1 d . . . C27 C 0.83244(15) 0.07538(14) 0.48364(15) 0.0588(5) Uani 1 1 d . . . C2 C 1.46248(14) 0.05944(14) 0.86729(15) 0.0579(5) Uani 1 1 d . . . H2 H 1.4493 0.0410 0.9280 0.069 Uiso 1 1 calc R . . C24 C 0.98304(14) 0.13291(14) 0.47457(14) 0.0556(5) Uani 1 1 d . . . C5 C 1.50260(14) 0.11554(14) 0.68785(16) 0.0581(5) Uani 1 1 d . . . H5 H 1.5169 0.1346 0.6278 0.070 Uiso 1 1 calc R . . C20 C 0.95008(17) 0.21672(17) 0.89319(15) 0.0691(6) Uani 1 1 d . . . H20 H 0.9560 0.2342 0.9586 0.083 Uiso 1 1 calc R . . B2 B 0.81232(15) 0.11895(16) 0.65956(17) 0.0518(5) Uani 1 1 d . . . C26 C 0.90212(16) 0.08771(16) 0.42289(15) 0.0672(6) Uani 1 1 d . . . H26 H 0.8950 0.0685 0.3579 0.081 Uiso 1 1 calc R . . C19 C 1.12924(19) 0.2511(2) 0.87697(18) 0.0967(9) Uani 1 1 d . . . H19A H 1.1347 0.2705 0.9440 0.145 Uiso 1 1 calc R . . H19B H 1.1464 0.3021 0.8384 0.145 Uiso 1 1 calc R . . H19C H 1.1733 0.1999 0.8732 0.145 Uiso 1 1 calc R . . C28 C 0.73408(16) 0.02809(17) 0.46012(19) 0.0762(7) Uani 1 1 d . . . H28A H 0.7389 -0.0331 0.4883 0.114 Uiso 1 1 calc R . . H28B H 0.7144 0.0234 0.3903 0.114 Uiso 1 1 calc R . . H28C H 0.6858 0.0636 0.4867 0.114 Uiso 1 1 calc R . . C25 C 1.07317(16) 0.15950(19) 0.43445(15) 0.0726(6) Uani 1 1 d . . . H25A H 1.0751 0.1248 0.3756 0.109 Uiso 1 1 calc R . . H25B H 1.1312 0.1459 0.4821 0.109 Uiso 1 1 calc R . . H25C H 1.0711 0.2249 0.4198 0.109 Uiso 1 1 calc R . . C10 C 1.55419(15) 0.42613(16) 0.63088(18) 0.0693(6) Uani 1 1 d . . . H10 H 1.6141 0.4539 0.6255 0.083 Uiso 1 1 calc R . . C29 C 1.65215(16) -0.11014(16) 0.8429(2) 0.0910(9) Uani 1 1 d . . . H29A H 1.6285 -0.1369 0.7795 0.136 Uiso 1 1 calc R . . H29B H 1.6776 -0.1585 0.8882 0.136 Uiso 1 1 calc R . . H29C H 1.7038 -0.0662 0.8381 0.136 Uiso 1 1 calc R . . C22 C 0.76573(17) 0.1692(2) 0.86244(18) 0.0831(7) Uani 1 1 d . . . H22A H 0.7160 0.1955 0.8124 0.125 Uiso 1 1 calc R . . H22B H 0.7643 0.2001 0.9236 0.125 Uiso 1 1 calc R . . H22C H 0.7530 0.1040 0.8690 0.125 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 F1 0.0704(7) 0.0567(7) 0.0737(8) -0.0123(6) 0.0151(6) 0.0039(6) F2 0.0665(7) 0.0634(7) 0.0688(7) 0.0234(6) 0.0065(6) 0.0067(6) F4 0.0697(7) 0.0654(7) 0.0842(8) 0.0048(6) 0.0199(6) -0.0203(6) N1 0.0488(8) 0.0466(8) 0.0579(9) 0.0077(7) 0.0137(7) -0.0020(7) O1 0.0536(8) 0.0586(8) 0.1080(12) 0.0263(9) 0.0005(8) 0.0071(7) F3 0.0459(6) 0.0870(9) 0.0792(8) -0.0007(7) 0.0086(5) 0.0126(6) N4 0.0443(8) 0.0521(9) 0.0537(9) -0.0028(7) 0.0064(6) -0.0034(7) N3 0.0442(8) 0.0542(9) 0.0522(8) 0.0011(7) 0.0157(6) -0.0002(7) N2 0.0409(7) 0.0429(8) 0.0536(8) 0.0050(7) 0.0099(6) 0.0034(6) C3 0.0450(9) 0.0548(11) 0.0580(11) 0.0100(9) 0.0097(8) 0.0020(8) C4 0.0367(8) 0.0482(10) 0.0573(10) 0.0076(8) 0.0083(7) -0.0007(7) C16 0.0395(8) 0.0458(9) 0.0509(9) 0.0011(8) 0.0102(7) 0.0030(7) C23 0.0429(9) 0.0493(10) 0.0496(10) 0.0006(8) 0.0106(7) 0.0023(8) C14 0.0404(9) 0.0505(10) 0.0497(9) 0.0012(8) 0.0112(7) 0.0002(7) C21 0.0629(12) 0.0679(12) 0.0550(11) 0.0032(10) 0.0245(9) 0.0052(10) C7 0.0412(9) 0.0483(10) 0.0443(9) 0.0036(8) 0.0091(7) 0.0019(7) C17 0.0426(9) 0.0514(10) 0.0519(10) -0.0040(8) 0.0108(7) -0.0034(8) C8 0.0437(9) 0.0489(10) 0.0462(9) 0.0048(8) 0.0095(7) 0.0002(7) C11 0.0616(12) 0.0529(11) 0.0863(15) 0.0153(11) 0.0205(11) -0.0082(10) C6 0.0454(10) 0.0569(12) 0.0882(15) 0.0066(11) 0.0197(10) 0.0082(9) C9 0.0431(9) 0.0627(12) 0.0628(11) 0.0094(10) 0.0099(8) -0.0034(8) C13 0.0433(9) 0.0446(9) 0.0535(10) 0.0075(8) 0.0104(7) 0.0013(7) C18 0.0604(11) 0.0689(13) 0.0550(11) -0.0104(10) 0.0110(9) -0.0071(10) C1 0.0381(9) 0.0481(10) 0.0816(14) 0.0157(10) 0.0000(9) -0.0030(8) C12 0.0418(8) 0.0435(9) 0.0491(9) 0.0046(8) 0.0096(7) 0.0039(7) C15 0.0411(9) 0.0480(10) 0.0546(10) 0.0049(8) 0.0089(7) 0.0049(7) B1 0.0509(11) 0.0424(11) 0.0532(11) 0.0056(9) 0.0098(9) 0.0020(9) C27 0.0587(11) 0.0561(11) 0.0572(11) -0.0042(9) -0.0014(9) -0.0007(9) C2 0.0498(10) 0.0603(11) 0.0617(11) 0.0149(10) 0.0045(9) -0.0015(9) C24 0.0570(11) 0.0621(11) 0.0478(10) 0.0030(9) 0.0100(8) 0.0077(9) C5 0.0498(10) 0.0587(11) 0.0687(12) 0.0117(10) 0.0187(9) 0.0071(9) C20 0.0772(14) 0.0835(15) 0.0496(11) -0.0114(11) 0.0191(10) -0.0025(12) B2 0.0393(10) 0.0564(12) 0.0610(12) 0.0032(10) 0.0121(9) -0.0028(9) C26 0.0748(14) 0.0755(14) 0.0496(11) -0.0064(10) 0.0067(10) 0.0037(12) C19 0.0816(17) 0.141(3) 0.0650(14) -0.0336(16) 0.0075(12) -0.0391(17) C28 0.0645(13) 0.0717(15) 0.0848(16) -0.0122(13) -0.0080(11) -0.0097(11) C25 0.0679(13) 0.1009(18) 0.0538(11) 0.0046(12) 0.0238(10) 0.0097(12) C10 0.0496(11) 0.0727(14) 0.0869(15) 0.0118(12) 0.0159(10) -0.0153(10) C29 0.0575(13) 0.0566(13) 0.154(3) 0.0164(16) 0.0055(15) 0.0148(11) C22 0.0710(14) 0.112(2) 0.0753(15) 0.0034(14) 0.0383(12) 0.0030(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag F1 B1 1.386(2) . ? F2 B1 1.367(2) . ? F4 B2 1.388(2) . ? N1 C11 1.336(2) . ? N1 C8 1.392(2) . ? N1 B1 1.549(2) . ? O1 C1 1.366(2) . ? O1 C29 1.424(3) . ? F3 B2 1.391(2) . ? N4 C27 1.349(2) . ? N4 C23 1.400(2) . ? N4 B2 1.541(3) . ? N3 C21 1.344(2) . ? N3 C17 1.403(2) . ? N3 B2 1.540(3) . ? N2 C15 1.344(2) . ? N2 C12 1.389(2) . ? N2 B1 1.551(2) . ? C3 C2 1.376(3) . ? C3 C4 1.395(3) . ? C3 H3 0.9300 . ? C4 C5 1.385(3) . ? C4 C7 1.475(2) . ? C16 C23 1.391(2) . ? C16 C17 1.401(2) . ? C16 C14 1.484(2) . ? C23 C24 1.428(3) . ? C14 C13 1.383(2) . ? C14 C15 1.392(3) . ? C21 C20 1.393(3) . ? C21 C22 1.487(3) . ? C7 C8 1.392(2) . ? C7 C12 1.408(2) . ? C17 C18 1.418(3) . ? C8 C9 1.413(2) . ? C11 C10 1.393(3) . ? C11 H11 0.9300 . ? C6 C1 1.382(3) . ? C6 C5 1.390(3) . ? C6 H6 0.9300 . ? C9 C10 1.366(3) . ? C9 H9 0.9300 . ? C13 C12 1.404(2) . ? C13 H13 0.9300 . ? C18 C20 1.382(3) . ? C18 C19 1.504(3) . ? C1 C2 1.382(3) . ? C15 H15 0.9300 . ? C27 C26 1.394(3) . ? C27 C28 1.495(3) . ? C2 H2 0.9300 . ? C24 C26 1.373(3) . ? C24 C25 1.494(3) . ? C5 H5 0.9300 . ? C20 H20 0.9300 . ? C26 H26 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C10 H10 0.9300 . ? C29 H29A 0.9600 . ? C29 H29B 0.9600 . ? C29 H29C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? 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 C11 N1 C8 107.71(16) . . ? C11 N1 B1 125.99(16) . . ? C8 N1 B1 125.22(15) . . ? C1 O1 C29 118.2(2) . . ? C27 N4 C23 108.11(16) . . ? C27 N4 B2 126.29(16) . . ? C23 N4 B2 125.41(15) . . ? C21 N3 C17 108.41(16) . . ? C21 N3 B2 126.13(16) . . ? C17 N3 B2 125.46(15) . . ? C15 N2 C12 107.21(14) . . ? C15 N2 B1 127.81(15) . . ? C12 N2 B1 124.53(14) . . ? C2 C3 C4 120.97(18) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 118.36(17) . . ? C5 C4 C7 122.50(17) . . ? C3 C4 C7 119.12(16) . . ? C23 C16 C17 121.21(16) . . ? C23 C16 C14 120.59(15) . . ? C17 C16 C14 118.12(16) . . ? C16 C23 N4 120.28(16) . . ? C16 C23 C24 132.07(17) . . ? N4 C23 C24 107.56(16) . . ? C13 C14 C15 106.57(15) . . ? C13 C14 C16 128.61(16) . . ? C15 C14 C16 124.75(16) . . ? N3 C21 C20 108.73(17) . . ? N3 C21 C22 123.7(2) . . ? C20 C21 C22 127.6(2) . . ? C8 C7 C12 120.09(16) . . ? C8 C7 C4 121.13(15) . . ? C12 C7 C4 118.75(15) . . ? C16 C17 N3 119.96(16) . . ? C16 C17 C18 132.12(17) . . ? N3 C17 C18 107.73(16) . . ? C7 C8 N1 120.58(15) . . ? C7 C8 C9 132.02(17) . . ? N1 C8 C9 107.36(15) . . ? N1 C11 C10 110.21(18) . . ? N1 C11 H11 124.9 . . ? C10 C11 H11 124.9 . . ? C1 C6 C5 119.41(19) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C10 C9 C8 107.44(18) . . ? C10 C9 H9 126.3 . . ? C8 C9 H9 126.3 . . ? C14 C13 C12 107.42(16) . . ? C14 C13 H13 126.3 . . ? C12 C13 H13 126.3 . . ? C20 C18 C17 105.93(18) . . ? C20 C18 C19 124.9(2) . . ? C17 C18 C19 129.14(19) . . ? O1 C1 C2 115.19(19) . . ? O1 C1 C6 124.5(2) . . ? C2 C1 C6 120.29(18) . . ? N2 C12 C13 108.14(14) . . ? N2 C12 C7 120.92(15) . . ? C13 C12 C7 130.86(16) . . ? N2 C15 C14 110.66(15) . . ? N2 C15 H15 124.7 . . ? C14 C15 H15 124.7 . . ? F2 B1 F1 109.82(16) . . ? F2 B1 N1 111.42(16) . . ? F1 B1 N1 109.11(16) . . ? F2 B1 N2 111.45(16) . . ? F1 B1 N2 109.44(16) . . ? N1 B1 N2 105.49(14) . . ? N4 C27 C26 109.15(17) . . ? N4 C27 C28 122.7(2) . . ? C26 C27 C28 128.1(2) . . ? C3 C2 C1 119.91(19) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C26 C24 C23 106.27(17) . . ? C26 C24 C25 125.02(19) . . ? C23 C24 C25 128.70(18) . . ? C4 C5 C6 121.04(19) . . ? C4 C5 H5 119.5 . . ? C6 C5 H5 119.5 . . ? C18 C20 C21 109.14(18) . . ? C18 C20 H20 125.4 . . ? C21 C20 H20 125.4 . . ? F4 B2 F3 109.09(15) . . ? F4 B2 N3 110.40(17) . . ? F3 B2 N3 110.20(17) . . ? F4 B2 N4 110.24(17) . . ? F3 B2 N4 109.96(16) . . ? N3 B2 N4 106.94(14) . . ? C24 C26 C27 108.90(18) . . ? C24 C26 H26 125.6 . . ? C27 C26 H26 125.6 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C9 C10 C11 107.27(18) . . ? C9 C10 H10 126.4 . . ? C11 C10 H10 126.4 . . ? O1 C29 H29A 109.5 . . ? O1 C29 H29B 109.5 . . ? H29A C29 H29B 109.5 . . ? O1 C29 H29C 109.5 . . ? H29A C29 H29C 109.5 . . ? H29B C29 H29C 109.5 . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C2 C3 C4 C5 0.8(3) . . . . ? C2 C3 C4 C7 -177.35(17) . . . . ? C17 C16 C23 N4 -1.5(3) . . . . ? C14 C16 C23 N4 -178.09(16) . . . . ? C17 C16 C23 C24 -177.3(2) . . . . ? C14 C16 C23 C24 6.0(3) . . . . ? C27 N4 C23 C16 -176.32(17) . . . . ? B2 N4 C23 C16 8.4(3) . . . . ? C27 N4 C23 C24 0.5(2) . . . . ? B2 N4 C23 C24 -174.82(17) . . . . ? C23 C16 C14 C13 -99.4(2) . . . . ? C17 C16 C14 C13 83.9(2) . . . . ? C23 C16 C14 C15 84.0(2) . . . . ? C17 C16 C14 C15 -92.7(2) . . . . ? C17 N3 C21 C20 -2.3(2) . . . . ? B2 N3 C21 C20 177.40(19) . . . . ? C17 N3 C21 C22 176.1(2) . . . . ? B2 N3 C21 C22 -4.2(3) . . . . ? C5 C4 C7 C8 -54.3(3) . . . . ? C3 C4 C7 C8 123.80(19) . . . . ? C5 C4 C7 C12 127.95(19) . . . . ? C3 C4 C7 C12 -54.0(2) . . . . ? C23 C16 C17 N3 -5.9(3) . . . . ? C14 C16 C17 N3 170.76(15) . . . . ? C23 C16 C17 C18 179.7(2) . . . . ? C14 C16 C17 C18 -3.6(3) . . . . ? C21 N3 C17 C16 -173.26(17) . . . . ? B2 N3 C17 C16 7.1(3) . . . . ? C21 N3 C17 C18 2.4(2) . . . . ? B2 N3 C17 C18 -177.28(18) . . . . ? C12 C7 C8 N1 4.0(3) . . . . ? C4 C7 C8 N1 -173.75(16) . . . . ? C12 C7 C8 C9 -178.46(19) . . . . ? C4 C7 C8 C9 3.8(3) . . . . ? C11 N1 C8 C7 177.52(18) . . . . ? B1 N1 C8 C7 8.8(3) . . . . ? C11 N1 C8 C9 -0.6(2) . . . . ? B1 N1 C8 C9 -169.26(17) . . . . ? C8 N1 C11 C10 0.8(3) . . . . ? B1 N1 C11 C10 169.37(19) . . . . ? C7 C8 C9 C10 -177.6(2) . . . . ? N1 C8 C9 C10 0.1(2) . . . . ? C15 C14 C13 C12 0.1(2) . . . . ? C16 C14 C13 C12 -176.94(17) . . . . ? C16 C17 C18 C20 173.4(2) . . . . ? N3 C17 C18 C20 -1.5(2) . . . . ? C16 C17 C18 C19 -9.6(4) . . . . ? N3 C17 C18 C19 175.5(2) . . . . ? C29 O1 C1 C2 -172.19(19) . . . . ? C29 O1 C1 C6 8.4(3) . . . . ? C5 C6 C1 O1 -179.39(18) . . . . ? C5 C6 C1 C2 1.2(3) . . . . ? C15 N2 C12 C13 -0.04(19) . . . . ? B1 N2 C12 C13 172.82(16) . . . . ? C15 N2 C12 C7 177.03(16) . . . . ? B1 N2 C12 C7 -10.1(3) . . . . ? C14 C13 C12 N2 -0.1(2) . . . . ? C14 C13 C12 C7 -176.73(18) . . . . ? C8 C7 C12 N2 -3.3(3) . . . . ? C4 C7 C12 N2 174.46(16) . . . . ? C8 C7 C12 C13 172.98(18) . . . . ? C4 C7 C12 C13 -9.2(3) . . . . ? C12 N2 C15 C14 0.1(2) . . . . ? B1 N2 C15 C14 -172.42(17) . . . . ? C13 C14 C15 N2 -0.2(2) . . . . ? C16 C14 C15 N2 177.05(16) . . . . ? C11 N1 B1 F2 53.6(3) . . . . ? C8 N1 B1 F2 -139.72(17) . . . . ? C11 N1 B1 F1 -67.8(2) . . . . ? C8 N1 B1 F1 98.9(2) . . . . ? C11 N1 B1 N2 174.73(18) . . . . ? C8 N1 B1 N2 -18.6(2) . . . . ? C15 N2 B1 F2 -48.4(2) . . . . ? C12 N2 B1 F2 140.22(17) . . . . ? C15 N2 B1 F1 73.2(2) . . . . ? C12 N2 B1 F1 -98.1(2) . . . . ? C15 N2 B1 N1 -169.49(16) . . . . ? C12 N2 B1 N1 19.2(2) . . . . ? C23 N4 C27 C26 0.0(2) . . . . ? B2 N4 C27 C26 175.21(18) . . . . ? C23 N4 C27 C28 178.24(19) . . . . ? B2 N4 C27 C28 -6.5(3) . . . . ? C4 C3 C2 C1 -1.0(3) . . . . ? O1 C1 C2 C3 -179.49(17) . . . . ? C6 C1 C2 C3 -0.1(3) . . . . ? C16 C23 C24 C26 175.5(2) . . . . ? N4 C23 C24 C26 -0.7(2) . . . . ? C16 C23 C24 C25 -4.3(4) . . . . ? N4 C23 C24 C25 179.4(2) . . . . ? C3 C4 C5 C6 0.4(3) . . . . ? C7 C4 C5 C6 178.48(18) . . . . ? C1 C6 C5 C4 -1.4(3) . . . . ? C17 C18 C20 C21 0.2(3) . . . . ? C19 C18 C20 C21 -177.0(2) . . . . ? N3 C21 C20 C18 1.3(3) . . . . ? C22 C21 C20 C18 -177.0(2) . . . . ? C21 N3 B2 F4 -60.6(3) . . . . ? C17 N3 B2 F4 119.00(19) . . . . ? C21 N3 B2 F3 60.0(3) . . . . ? C17 N3 B2 F3 -120.43(18) . . . . ? C21 N3 B2 N4 179.47(18) . . . . ? C17 N3 B2 N4 -0.9(2) . . . . ? C27 N4 B2 F4 58.7(2) . . . . ? C23 N4 B2 F4 -126.84(18) . . . . ? C27 N4 B2 F3 -61.6(2) . . . . ? C23 N4 B2 F3 112.85(19) . . . . ? C27 N4 B2 N3 178.76(17) . . . . ? C23 N4 B2 N3 -6.8(2) . . . . ? C23 C24 C26 C27 0.7(2) . . . . ? C25 C24 C26 C27 -179.5(2) . . . . ? N4 C27 C26 C24 -0.4(3) . . . . ? C28 C27 C26 C24 -178.6(2) . . . . ? C8 C9 C10 C11 0.3(3) . . . . ? N1 C11 C10 C9 -0.7(3) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 67.54 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.138 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.035 # Attachment '- 2c.cif' data_110112b_0m _database_code_depnum_ccdc_archive 'CCDC 867742' #TrackingRef '- 2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C24 H14 B2 Cl2 F4 N4' _chemical_formula_weight 526.91 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' 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 10.6288(9) _cell_length_b 11.0950(9) _cell_length_c 19.9094(17) _cell_angle_alpha 90.00 _cell_angle_beta 103.6880(10) _cell_angle_gamma 90.00 _cell_volume 2281.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7122 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 27.15 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.534 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.340 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9290 _exptl_absorpt_correction_T_max 0.9382 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 19393 _diffrn_reflns_av_R_equivalents 0.0338 _diffrn_reflns_av_sigmaI/netI 0.0307 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 27.60 _reflns_number_total 5248 _reflns_number_gt 3784 _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^)+(0.0801P)^2^+1.3790P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5248 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0742 _refine_ls_R_factor_gt 0.0527 _refine_ls_wR_factor_ref 0.1635 _refine_ls_wR_factor_gt 0.1456 _refine_ls_goodness_of_fit_ref 1.040 _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 B1 B 0.2107(3) 1.0034(2) 0.04840(15) 0.0418(6) Uani 1 1 d . . . C1 C 0.4087(3) 1.1395(3) 0.0541(2) 0.0770(11) Uani 1 1 d . . . H1 H 0.3635 1.2008 0.0268 0.092 Uiso 1 1 calc R . . Cl1 Cl 0.54107(8) 0.65431(8) 0.07173(4) 0.0682(3) Uani 1 1 d . . . F1 F 0.17507(18) 0.99253(19) -0.02145(9) 0.0713(5) Uani 1 1 d . . . N1 N 0.3554(2) 1.03944(19) 0.07131(12) 0.0478(5) Uani 1 1 d . . . B2 B -0.1083(3) 0.3796(2) 0.13481(15) 0.0414(6) Uani 1 1 d . . . C2 C 0.5432(3) 1.1397(4) 0.0829(3) 0.0974(16) Uani 1 1 d . . . H2 H 0.6011 1.2005 0.0787 0.117 Uiso 1 1 calc R . . Cl2 Cl 0.51680(9) 0.93472(9) 0.29021(5) 0.0847(3) Uani 1 1 d . . . F2 F 0.13569(16) 1.08863(14) 0.06970(11) 0.0666(5) Uani 1 1 d . . . N2 N 0.20005(17) 0.88048(16) 0.08444(10) 0.0346(4) Uani 1 1 d . . . C3 C 0.5724(3) 1.0348(3) 0.1179(2) 0.0716(10) Uani 1 1 d . . . H3 H 0.6544 1.0092 0.1413 0.086 Uiso 1 1 calc R . . F3 F -0.04313(18) 0.28243(14) 0.11736(9) 0.0653(5) Uani 1 1 d . . . N3 N -0.02300(18) 0.44973(17) 0.19597(10) 0.0378(4) Uani 1 1 d . . . C4 C 0.4545(2) 0.9709(2) 0.11232(14) 0.0465(6) Uani 1 1 d . . . F4 F -0.22147(16) 0.34280(15) 0.15152(9) 0.0614(5) Uani 1 1 d . . . N4 N -0.13854(18) 0.47138(16) 0.07463(10) 0.0363(4) Uani 1 1 d . . . C5 C 0.4295(2) 0.8626(2) 0.13995(12) 0.0370(5) Uani 1 1 d . . . C6 C 0.3023(2) 0.81788(19) 0.12710(12) 0.0335(5) Uani 1 1 d . . . C7 C 0.2530(2) 0.71261(19) 0.14945(12) 0.0340(5) Uani 1 1 d . . . H7 H 0.2998 0.6549 0.1790 0.041 Uiso 1 1 calc R . . C8 C 0.1198(2) 0.70988(19) 0.11906(11) 0.0318(4) Uani 1 1 d . . . C9 C 0.0921(2) 0.81548(19) 0.07920(12) 0.0341(5) Uani 1 1 d . . . H9 H 0.0107 0.8370 0.0530 0.041 Uiso 1 1 calc R . . C10 C 0.5397(2) 0.7940(2) 0.18377(12) 0.0378(5) Uani 1 1 d . . . C11 C 0.6009(2) 0.7015(2) 0.15662(13) 0.0437(6) Uani 1 1 d . . . C12 C 0.7088(3) 0.6429(3) 0.19532(17) 0.0566(7) Uani 1 1 d . . . H12 H 0.7476 0.5812 0.1759 0.068 Uiso 1 1 calc R . . C13 C 0.7576(3) 0.6765(3) 0.26219(18) 0.0651(9) Uani 1 1 d . . . H13 H 0.8316 0.6390 0.2881 0.078 Uiso 1 1 calc R . . C14 C 0.6987(3) 0.7653(3) 0.29172(16) 0.0661(9) Uani 1 1 d . . . H14 H 0.7312 0.7866 0.3377 0.079 Uiso 1 1 calc R . . C15 C 0.5906(3) 0.8227(2) 0.25253(14) 0.0508(7) Uani 1 1 d . . . C16 C 0.0324(2) 0.61131(18) 0.12545(11) 0.0303(4) Uani 1 1 d . . . C17 C 0.0482(2) 0.55219(19) 0.18960(12) 0.0334(5) Uani 1 1 d . . . C18 C 0.1147(2) 0.5869(2) 0.25635(12) 0.0388(5) Uani 1 1 d . . . H18 H 0.1702 0.6525 0.2675 0.047 Uiso 1 1 calc R . . C19 C 0.0831(3) 0.5062(3) 0.30242(13) 0.0493(6) Uani 1 1 d . . . H19 H 0.1122 0.5075 0.3503 0.059 Uiso 1 1 calc R . . C20 C -0.0007(3) 0.4228(2) 0.26346(13) 0.0488(6) Uani 1 1 d . . . H20 H -0.0363 0.3574 0.2816 0.059 Uiso 1 1 calc R . . C21 C -0.0662(2) 0.57375(19) 0.06872(11) 0.0325(5) Uani 1 1 d . . . C22 C -0.1114(2) 0.6202(2) 0.00156(12) 0.0397(5) Uani 1 1 d . . . H22 H -0.0799 0.6875 -0.0169 0.048 Uiso 1 1 calc R . . C23 C -0.2118(3) 0.5463(2) -0.03162(13) 0.0482(6) Uani 1 1 d . . . H23 H -0.2618 0.5556 -0.0764 0.058 Uiso 1 1 calc R . . C24 C -0.2240(2) 0.4560(2) 0.01424(13) 0.0464(6) Uani 1 1 d . . . H24 H -0.2835 0.3933 0.0044 0.056 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 B1 0.0338(13) 0.0389(13) 0.0476(16) 0.0120(12) -0.0005(12) -0.0048(11) C1 0.0527(18) 0.0613(18) 0.106(3) 0.0409(19) -0.0025(17) -0.0174(15) Cl1 0.0692(5) 0.0840(6) 0.0495(4) -0.0102(4) 0.0103(4) 0.0105(4) F1 0.0714(12) 0.0885(13) 0.0436(9) 0.0205(8) -0.0069(8) -0.0250(10) N1 0.0355(11) 0.0416(11) 0.0604(14) 0.0168(10) -0.0003(10) -0.0076(8) B2 0.0436(15) 0.0364(13) 0.0430(15) 0.0027(11) 0.0080(12) -0.0086(11) C2 0.0507(19) 0.081(2) 0.146(4) 0.053(3) -0.007(2) -0.0299(17) Cl2 0.0787(6) 0.0911(6) 0.0711(6) -0.0342(5) -0.0084(4) 0.0307(5) F2 0.0503(9) 0.0408(8) 0.1076(15) 0.0131(9) 0.0168(9) 0.0083(7) N2 0.0272(9) 0.0342(9) 0.0388(10) 0.0073(8) 0.0005(7) -0.0013(7) C3 0.0360(14) 0.069(2) 0.100(3) 0.0269(18) -0.0022(15) -0.0173(13) F3 0.0912(13) 0.0388(8) 0.0644(11) -0.0012(7) 0.0155(9) 0.0083(8) N3 0.0364(10) 0.0368(9) 0.0376(10) 0.0063(8) 0.0037(8) -0.0045(8) C4 0.0306(12) 0.0465(13) 0.0568(16) 0.0086(11) -0.0006(11) -0.0064(10) F4 0.0520(9) 0.0674(10) 0.0627(10) 0.0084(8) 0.0094(8) -0.0269(8) N4 0.0336(10) 0.0354(9) 0.0370(10) -0.0016(8) 0.0028(8) -0.0072(8) C5 0.0288(11) 0.0393(11) 0.0398(12) 0.0020(9) 0.0016(9) -0.0013(9) C6 0.0279(11) 0.0322(10) 0.0374(12) 0.0029(8) 0.0018(9) -0.0001(8) C7 0.0300(11) 0.0322(10) 0.0370(12) 0.0026(9) 0.0026(9) 0.0012(8) C8 0.0273(10) 0.0320(10) 0.0349(11) 0.0004(8) 0.0051(9) -0.0013(8) C9 0.0254(10) 0.0341(10) 0.0392(12) 0.0026(9) 0.0007(9) -0.0009(8) C10 0.0266(10) 0.0394(11) 0.0435(13) 0.0041(10) 0.0007(9) -0.0020(9) C11 0.0353(12) 0.0502(13) 0.0447(14) 0.0020(11) 0.0078(10) -0.0003(10) C12 0.0409(14) 0.0586(16) 0.0703(19) 0.0025(14) 0.0134(13) 0.0148(12) C13 0.0424(16) 0.072(2) 0.070(2) 0.0071(16) -0.0080(14) 0.0192(14) C14 0.0549(17) 0.078(2) 0.0519(17) -0.0095(15) -0.0149(14) 0.0166(15) C15 0.0418(14) 0.0532(15) 0.0500(15) -0.0085(12) -0.0038(12) 0.0076(11) C16 0.0264(10) 0.0285(9) 0.0353(11) -0.0008(8) 0.0061(8) 0.0009(8) C17 0.0283(10) 0.0330(10) 0.0368(11) 0.0029(9) 0.0034(9) -0.0010(8) C18 0.0338(12) 0.0424(12) 0.0368(12) 0.0005(10) 0.0012(9) -0.0016(9) C19 0.0465(14) 0.0643(16) 0.0333(12) 0.0074(11) 0.0020(11) -0.0035(12) C20 0.0504(15) 0.0527(15) 0.0408(13) 0.0135(11) 0.0059(11) -0.0077(12) C21 0.0300(11) 0.0316(10) 0.0343(11) 0.0008(8) 0.0047(9) -0.0005(8) C22 0.0427(13) 0.0396(12) 0.0346(12) 0.0007(9) 0.0045(10) -0.0003(10) C23 0.0480(15) 0.0516(14) 0.0376(13) -0.0031(11) -0.0044(11) -0.0010(11) C24 0.0410(13) 0.0477(13) 0.0444(14) -0.0060(11) -0.0023(11) -0.0099(11) _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 B1 F1 1.357(3) . ? B1 F2 1.368(3) . ? B1 N1 1.549(3) . ? B1 N2 1.557(3) . ? C1 N1 1.328(3) . ? C1 C2 1.409(5) . ? Cl1 C11 1.739(3) . ? N1 C4 1.395(3) . ? B2 F3 1.370(3) . ? B2 F4 1.383(3) . ? B2 N3 1.545(3) . ? B2 N4 1.547(3) . ? C2 C3 1.355(5) . ? Cl2 C15 1.732(3) . ? N2 C9 1.338(3) . ? N2 C6 1.396(3) . ? C3 C4 1.420(4) . ? N3 C20 1.342(3) . ? N3 C17 1.388(3) . ? C4 C5 1.373(3) . ? N4 C24 1.335(3) . ? N4 C21 1.392(3) . ? C5 C6 1.406(3) . ? C5 C10 1.493(3) . ? C6 C7 1.395(3) . ? C7 C8 1.402(3) . ? C8 C9 1.407(3) . ? C8 C16 1.460(3) . ? C10 C15 1.385(3) . ? C10 C11 1.391(4) . ? C11 C12 1.383(4) . ? C12 C13 1.362(4) . ? C13 C14 1.372(4) . ? C14 C15 1.383(4) . ? C16 C21 1.410(3) . ? C16 C17 1.410(3) . ? C17 C18 1.403(3) . ? C18 C19 1.379(4) . ? C19 C20 1.387(4) . ? C21 C22 1.407(3) . ? C22 C23 1.383(3) . ? C23 C24 1.382(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag F1 B1 F2 109.7(2) . . ? F1 B1 N1 110.0(2) . . ? F2 B1 N1 109.9(2) . . ? F1 B1 N2 111.2(2) . . ? F2 B1 N2 110.6(2) . . ? N1 B1 N2 105.41(18) . . ? N1 C1 C2 110.5(3) . . ? C1 N1 C4 107.3(2) . . ? C1 N1 B1 126.4(2) . . ? C4 N1 B1 126.22(19) . . ? F3 B2 F4 110.4(2) . . ? F3 B2 N3 111.0(2) . . ? F4 B2 N3 109.9(2) . . ? F3 B2 N4 110.3(2) . . ? F4 B2 N4 110.3(2) . . ? N3 B2 N4 104.75(18) . . ? C3 C2 C1 107.1(3) . . ? C9 N2 C6 107.99(17) . . ? C9 N2 B1 126.20(18) . . ? C6 N2 B1 125.81(18) . . ? C2 C3 C4 107.3(3) . . ? C20 N3 C17 107.6(2) . . ? C20 N3 B2 127.5(2) . . ? C17 N3 B2 124.85(19) . . ? C5 C4 N1 121.3(2) . . ? C5 C4 C3 131.0(2) . . ? N1 C4 C3 107.7(2) . . ? C24 N4 C21 107.44(19) . . ? C24 N4 B2 125.9(2) . . ? C21 N4 B2 125.78(18) . . ? C4 C5 C6 120.3(2) . . ? C4 C5 C10 118.7(2) . . ? C6 C5 C10 120.9(2) . . ? C7 C6 N2 108.28(18) . . ? C7 C6 C5 130.9(2) . . ? N2 C6 C5 120.78(19) . . ? C6 C7 C8 107.30(18) . . ? C7 C8 C9 106.29(18) . . ? C7 C8 C16 125.23(19) . . ? C9 C8 C16 128.37(19) . . ? N2 C9 C8 110.12(18) . . ? C15 C10 C11 116.4(2) . . ? C15 C10 C5 122.0(2) . . ? C11 C10 C5 121.6(2) . . ? C12 C11 C10 122.2(2) . . ? C12 C11 Cl1 117.7(2) . . ? C10 C11 Cl1 120.17(19) . . ? C13 C12 C11 119.4(3) . . ? C12 C13 C14 120.6(3) . . ? C13 C14 C15 119.5(3) . . ? C14 C15 C10 122.0(3) . . ? C14 C15 Cl2 119.2(2) . . ? C10 C15 Cl2 118.83(19) . . ? C21 C16 C17 119.64(19) . . ? C21 C16 C8 121.30(19) . . ? C17 C16 C8 119.06(19) . . ? N3 C17 C18 107.56(19) . . ? N3 C17 C16 120.88(19) . . ? C18 C17 C16 130.9(2) . . ? C19 C18 C17 107.7(2) . . ? C18 C19 C20 106.6(2) . . ? N3 C20 C19 110.5(2) . . ? N4 C21 C22 107.91(19) . . ? N4 C21 C16 119.63(19) . . ? C22 C21 C16 132.5(2) . . ? C23 C22 C21 106.8(2) . . ? C24 C23 C22 107.2(2) . . ? N4 C24 C23 110.6(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.60 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.783 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.055 # Attachment '- 2d.cif' data_110322a_0m _database_code_depnum_ccdc_archive 'CCDC 867743' #TrackingRef '- 2d.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H22 B2 Cl2 F4 N4' _chemical_formula_weight 583.02 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' 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)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 19.4958(14) _cell_length_b 14.4053(11) _cell_length_c 20.2393(15) _cell_angle_alpha 90.00 _cell_angle_beta 91.3190(10) _cell_angle_gamma 90.00 _cell_volume 5682.6(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6241 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 20.82 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2384 _exptl_absorpt_coefficient_mu 0.280 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9566 _exptl_absorpt_correction_T_max 0.9645 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 48743 _diffrn_reflns_av_R_equivalents 0.0694 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 27.56 _reflns_number_total 13059 _reflns_number_gt 4986 _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^)+(0.1043P)^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 0.0007(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 13059 _refine_ls_number_parameters 730 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1816 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.2348 _refine_ls_wR_factor_gt 0.1787 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.7418(2) 0.2633(3) 1.1249(2) 0.0567(11) Uani 1 1 d . . . B2 B 0.6087(2) 0.1879(4) 0.7686(2) 0.0674(12) Uani 1 1 d . . . B3 B 0.3871(2) 0.3053(3) 0.2799(2) 0.0621(11) Uani 1 1 d . . . B4 B 0.7709(2) 0.2762(3) 0.4037(2) 0.0637(12) Uani 1 1 d . . . C1 C 0.8223(2) 0.2917(4) 1.2254(2) 0.0957(16) Uani 1 1 d . . . H1 H 0.7878 0.3014 1.2556 0.115 Uiso 1 1 calc R . . C2 C 0.8926(2) 0.2965(4) 1.2407(2) 0.0950(15) Uani 1 1 d . . . H2 H 0.9129 0.3079 1.2819 0.114 Uiso 1 1 calc R . . C3 C 0.92524(19) 0.2812(3) 1.18334(19) 0.0720(11) Uani 1 1 d . . . H3 H 0.9724 0.2822 1.1778 0.086 Uiso 1 1 calc R . . C4 C 0.87568(17) 0.2637(3) 1.13403(17) 0.0593(9) Uani 1 1 d . . . C5 C 0.88103(17) 0.2405(3) 1.06790(17) 0.0608(10) Uani 1 1 d . . . C6 C 0.82344(17) 0.2247(3) 1.02795(17) 0.0592(9) Uani 1 1 d . . . C7 C 0.81558(18) 0.2049(3) 0.96033(17) 0.0675(11) Uani 1 1 d . . . H7 H 0.8507 0.1943 0.9309 0.081 Uiso 1 1 calc R . . C8 C 0.74569(18) 0.2043(3) 0.94546(16) 0.0603(10) Uani 1 1 d . . . C9 C 0.71270(18) 0.2220(3) 1.00410(17) 0.0659(10) Uani 1 1 d . . . H9 H 0.6653 0.2247 1.0083 0.079 Uiso 1 1 calc R . . C10 C 0.95111(19) 0.2318(4) 1.04064(18) 0.0773(13) Uani 1 1 d . . . C11 C 0.9884(2) 0.1494(5) 1.0475(2) 0.1047(18) Uani 1 1 d . . . C12 C 1.0568(3) 0.1476(7) 1.0254(3) 0.156(3) Uani 1 1 d . . . H12 H 1.0829 0.0941 1.0313 0.188 Uiso 1 1 calc R . . C13 C 1.0850(4) 0.2224(10) 0.9958(4) 0.200(7) Uani 1 1 d . . . H13 H 1.1297 0.2194 0.9808 0.240 Uiso 1 1 calc R . . C14 C 1.0495(4) 0.2987(7) 0.9884(4) 0.171(4) Uani 1 1 d . . . H14 H 1.0697 0.3497 0.9684 0.205 Uiso 1 1 calc R . . C15 C 0.9821(3) 0.3056(5) 1.0098(3) 0.1157(19) Uani 1 1 d . . . C16 C 0.69658(17) 0.1125(3) 0.85058(18) 0.0598(9) Uani 1 1 d . . . C17 C 0.72289(19) 0.0212(3) 0.8636(2) 0.0763(12) Uani 1 1 d . . . C18 C 0.6959(2) -0.0329(3) 0.8134(3) 0.0916(14) Uani 1 1 d . . . H18 H 0.7047 -0.0959 0.8081 0.110 Uiso 1 1 calc R . . C19 C 0.6537(2) 0.0195(4) 0.7720(2) 0.0812(12) Uani 1 1 d . . . C20 C 0.7703(2) -0.0112(3) 0.9174(2) 0.1048(16) Uani 1 1 d . . . H20A H 0.7718 -0.0778 0.9174 0.157 Uiso 1 1 calc R . . H20B H 0.7543 0.0103 0.9591 0.157 Uiso 1 1 calc R . . H20C H 0.8154 0.0129 0.9102 0.157 Uiso 1 1 calc R . . C21 C 0.6119(3) -0.0116(4) 0.7135(3) 0.131(2) Uani 1 1 d . . . H21A H 0.5641 -0.0021 0.7219 0.197 Uiso 1 1 calc R . . H21B H 0.6200 -0.0763 0.7057 0.197 Uiso 1 1 calc R . . H21C H 0.6245 0.0236 0.6754 0.197 Uiso 1 1 calc R . . C22 C 0.70849(17) 0.1969(3) 0.88115(17) 0.0580(9) Uani 1 1 d . . . C23 C 0.68187(19) 0.2791(3) 0.85477(18) 0.0643(10) Uani 1 1 d . . . C24 C 0.6930(2) 0.3738(3) 0.8716(2) 0.0819(12) Uani 1 1 d . . . C25 C 0.6553(3) 0.4245(4) 0.8275(3) 0.1066(16) Uani 1 1 d . . . H25 H 0.6531 0.4890 0.8266 0.128 Uiso 1 1 calc R . . C26 C 0.6204(2) 0.3656(4) 0.7837(3) 0.0991(15) Uani 1 1 d . . . C27 C 0.7395(3) 0.4154(3) 0.9234(2) 0.1174(18) Uani 1 1 d . . . H27A H 0.7376 0.4818 0.9204 0.176 Uiso 1 1 calc R . . H27B H 0.7857 0.3948 0.9167 0.176 Uiso 1 1 calc R . . H27C H 0.7252 0.3961 0.9663 0.176 Uiso 1 1 calc R . . C28 C 0.5728(3) 0.3902(4) 0.7275(3) 0.150(2) Uani 1 1 d . . . H28A H 0.5923 0.3705 0.6867 0.225 Uiso 1 1 calc R . . H28B H 0.5660 0.4562 0.7265 0.225 Uiso 1 1 calc R . . H28C H 0.5295 0.3599 0.7331 0.225 Uiso 1 1 calc R . . C29 C 0.2829(2) 0.3089(3) 0.1988(2) 0.0823(13) Uani 1 1 d . . . H29 H 0.2502 0.3221 0.2302 0.099 Uiso 1 1 calc R . . C30 C 0.2688(2) 0.2958(3) 0.1323(2) 0.0850(13) Uani 1 1 d . . . H30 H 0.2257 0.2979 0.1116 0.102 Uiso 1 1 calc R . . C31 C 0.3295(2) 0.2794(3) 0.10232(19) 0.0704(11) Uani 1 1 d . . . H31 H 0.3358 0.2685 0.0576 0.085 Uiso 1 1 calc R . . C32 C 0.38065(17) 0.2819(3) 0.15221(16) 0.0569(9) Uani 1 1 d . . . C33 C 0.45091(17) 0.2700(2) 0.14933(16) 0.0555(9) Uani 1 1 d . . . C34 C 0.49241(16) 0.2748(2) 0.20633(16) 0.0533(9) Uani 1 1 d . . . C35 C 0.56342(18) 0.2659(3) 0.21565(17) 0.0631(10) Uani 1 1 d . . . H35 H 0.5950 0.2535 0.1831 0.076 Uiso 1 1 calc R . . C36 C 0.57804(17) 0.2790(3) 0.28190(17) 0.0577(9) Uani 1 1 d . . . C37 C 0.51503(18) 0.2954(3) 0.31095(18) 0.0637(10) Uani 1 1 d . . . H37 H 0.5097 0.3067 0.3558 0.076 Uiso 1 1 calc R . . C38 C 0.48124(19) 0.2545(3) 0.08365(18) 0.0690(11) Uani 1 1 d . . . C39 C 0.5042(2) 0.3275(4) 0.0458(2) 0.0966(15) Uani 1 1 d . . . C40 C 0.5283(3) 0.3161(6) -0.0167(3) 0.131(2) Uani 1 1 d . . . H40 H 0.5446 0.3667 -0.0402 0.158 Uiso 1 1 calc R . . C41 C 0.5281(3) 0.2315(7) -0.0437(3) 0.135(3) Uani 1 1 d . . . H41 H 0.5419 0.2237 -0.0870 0.162 Uiso 1 1 calc R . . C42 C 0.5079(3) 0.1573(5) -0.0085(3) 0.141(3) Uani 1 1 d . . . H42 H 0.5095 0.0985 -0.0273 0.170 Uiso 1 1 calc R . . C43 C 0.4849(2) 0.1676(4) 0.0555(2) 0.1059(17) Uani 1 1 d . . . C44 C 0.64534(17) 0.2767(3) 0.31734(16) 0.0572(9) Uani 1 1 d . . . C45 C 0.67050(18) 0.1924(3) 0.34207(18) 0.0640(10) Uani 1 1 d . . . C46 C 0.6465(2) 0.0998(3) 0.3360(2) 0.0856(13) Uani 1 1 d . . . C47 C 0.6951(3) 0.0462(3) 0.3678(3) 0.1038(16) Uani 1 1 d . . . H47 H 0.6932 -0.0180 0.3719 0.125 Uiso 1 1 calc R . . C48 C 0.7474(2) 0.1017(3) 0.3929(2) 0.0828(12) Uani 1 1 d . . . C49 C 0.5820(3) 0.0650(4) 0.3020(3) 0.127(2) Uani 1 1 d . . . H49A H 0.5787 -0.0010 0.3077 0.191 Uiso 1 1 calc R . . H49B H 0.5833 0.0793 0.2557 0.191 Uiso 1 1 calc R . . H49C H 0.5429 0.0945 0.3209 0.191 Uiso 1 1 calc R . . C50 C 0.8104(3) 0.0733(3) 0.4314(2) 0.1096(17) Uani 1 1 d . . . H50A H 0.8504 0.0943 0.4090 0.164 Uiso 1 1 calc R . . H50B H 0.8116 0.0069 0.4353 0.164 Uiso 1 1 calc R . . H50C H 0.8096 0.1006 0.4747 0.164 Uiso 1 1 calc R . . C51 C 0.68142(18) 0.3591(3) 0.32676(16) 0.0579(9) Uani 1 1 d . . . C52 C 0.6721(2) 0.4497(3) 0.3004(2) 0.0768(12) Uani 1 1 d . . . C53 C 0.7254(3) 0.5019(3) 0.3238(2) 0.0969(15) Uani 1 1 d . . . H53 H 0.7323 0.5644 0.3148 0.116 Uiso 1 1 calc R . . C54 C 0.7679(2) 0.4464(3) 0.3635(2) 0.0802(12) Uani 1 1 d . . . C55 C 0.6162(2) 0.4851(3) 0.2542(2) 0.0988(15) Uani 1 1 d . . . H55A H 0.6244 0.5493 0.2442 0.148 Uiso 1 1 calc R . . H55B H 0.5726 0.4791 0.2749 0.148 Uiso 1 1 calc R . . H55C H 0.6159 0.4496 0.2141 0.148 Uiso 1 1 calc R . . C56 C 0.8329(2) 0.4735(3) 0.3999(2) 0.1084(16) Uani 1 1 d . . . H56A H 0.8319 0.4504 0.4443 0.163 Uiso 1 1 calc R . . H56B H 0.8368 0.5400 0.4007 0.163 Uiso 1 1 calc R . . H56C H 0.8715 0.4476 0.3778 0.163 Uiso 1 1 calc R . . Cl1 Cl 0.95188(9) 0.05604(12) 1.08388(8) 0.1402(6) Uani 1 1 d . . . Cl2 Cl 0.93559(11) 0.40754(15) 0.99820(11) 0.1831(9) Uani 1 1 d . . . Cl3 Cl 0.50591(11) 0.43864(12) 0.08146(9) 0.1646(8) Uani 1 1 d . . . Cl4 Cl 0.45892(12) 0.07321(12) 0.10050(10) 0.1945(11) Uani 1 1 d . . . F1 F 0.70110(10) 0.19768(15) 1.15445(10) 0.0697(6) Uani 1 1 d . . . F2 F 0.70764(11) 0.34681(15) 1.12474(11) 0.0813(7) Uani 1 1 d . . . F3 F 0.54164(10) 0.17374(19) 0.78888(12) 0.0973(8) Uani 1 1 d . . . F4 F 0.60950(12) 0.19277(18) 0.70069(11) 0.0941(8) Uani 1 1 d . . . F5 F 0.36428(11) 0.23566(18) 0.32036(11) 0.0878(7) Uani 1 1 d . . . F6 F 0.37559(11) 0.38924(18) 0.30986(11) 0.0894(7) Uani 1 1 d . . . F7 F 0.84025(11) 0.26857(17) 0.39444(13) 0.0973(8) Uani 1 1 d . . . F8 F 0.75870(14) 0.28798(18) 0.47059(10) 0.0987(8) Uani 1 1 d . . . N1 N 0.81154(14) 0.2715(2) 1.16182(14) 0.0662(9) Uani 1 1 d . . . N2 N 0.75839(13) 0.2348(2) 1.05406(13) 0.0587(8) Uani 1 1 d . . . N3 N 0.63721(15) 0.2771(2) 0.79960(15) 0.0706(9) Uani 1 1 d . . . N4 N 0.65412(14) 0.1081(2) 0.79372(14) 0.0611(8) Uani 1 1 d . . . N5 N 0.35010(14) 0.3000(2) 0.21176(14) 0.0611(8) Uani 1 1 d . . . N6 N 0.46375(13) 0.2928(2) 0.26695(13) 0.0565(8) Uani 1 1 d . . . N7 N 0.73295(15) 0.1912(2) 0.37771(14) 0.0616(8) Uani 1 1 d . . . N8 N 0.74204(15) 0.3602(2) 0.36512(13) 0.0603(8) 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 B1 0.039(2) 0.073(3) 0.058(3) -0.002(2) 0.0014(19) 0.009(2) B2 0.046(3) 0.103(4) 0.052(3) 0.005(3) -0.009(2) 0.002(2) B3 0.051(3) 0.079(3) 0.057(3) -0.008(2) 0.011(2) 0.012(2) B4 0.051(3) 0.089(3) 0.050(3) -0.001(2) -0.008(2) 0.007(2) C1 0.062(3) 0.168(5) 0.057(3) -0.033(3) 0.000(2) 0.010(3) C2 0.061(3) 0.159(5) 0.064(3) -0.034(3) -0.014(2) 0.009(3) C3 0.048(2) 0.107(3) 0.061(2) -0.016(2) -0.0054(19) 0.001(2) C4 0.041(2) 0.084(3) 0.053(2) -0.0074(19) -0.0002(17) 0.0041(18) C5 0.045(2) 0.083(3) 0.055(2) 0.0001(19) 0.0009(17) -0.0004(18) C6 0.043(2) 0.085(3) 0.050(2) -0.0002(19) 0.0023(17) -0.0047(18) C7 0.048(2) 0.105(3) 0.050(2) -0.001(2) 0.0089(17) -0.001(2) C8 0.049(2) 0.086(3) 0.046(2) 0.0018(19) -0.0045(17) -0.0043(18) C9 0.043(2) 0.100(3) 0.054(2) 0.001(2) -0.0058(18) -0.0014(19) C10 0.043(2) 0.140(4) 0.049(2) -0.015(2) 0.0036(18) -0.013(3) C11 0.063(3) 0.185(6) 0.065(3) -0.040(3) -0.013(2) 0.047(3) C12 0.066(4) 0.307(11) 0.096(5) -0.065(6) -0.011(3) 0.063(5) C13 0.060(5) 0.44(2) 0.098(6) -0.079(9) 0.018(4) -0.027(7) C14 0.091(5) 0.314(13) 0.110(5) -0.047(7) 0.038(5) -0.095(6) C15 0.075(4) 0.180(6) 0.093(4) -0.008(4) 0.018(3) -0.036(4) C16 0.047(2) 0.076(3) 0.056(2) 0.007(2) -0.0007(18) -0.0087(19) C17 0.055(2) 0.085(3) 0.089(3) 0.020(3) -0.001(2) -0.013(2) C18 0.082(3) 0.072(3) 0.120(4) 0.008(3) -0.010(3) -0.017(2) C19 0.067(3) 0.089(3) 0.087(3) -0.004(3) -0.006(2) -0.021(2) C20 0.097(3) 0.101(4) 0.116(4) 0.036(3) -0.022(3) -0.001(3) C21 0.124(4) 0.124(5) 0.144(5) -0.040(4) -0.042(4) -0.034(4) C22 0.0383(19) 0.086(3) 0.050(2) 0.005(2) -0.0006(16) 0.0003(18) C23 0.055(2) 0.082(3) 0.055(2) -0.004(2) -0.0058(19) 0.000(2) C24 0.082(3) 0.086(3) 0.077(3) -0.009(3) -0.012(2) 0.009(2) C25 0.109(4) 0.081(3) 0.128(4) 0.001(3) -0.036(3) 0.010(3) C26 0.091(3) 0.095(4) 0.111(4) 0.022(3) -0.023(3) 0.016(3) C27 0.157(5) 0.093(4) 0.101(4) -0.018(3) -0.032(4) -0.009(3) C28 0.142(5) 0.127(5) 0.177(6) 0.042(4) -0.085(5) 0.015(4) C29 0.045(2) 0.126(4) 0.076(3) -0.010(3) 0.001(2) 0.016(2) C30 0.058(3) 0.118(4) 0.078(3) -0.008(3) -0.018(2) 0.013(2) C31 0.060(3) 0.096(3) 0.054(2) -0.006(2) -0.006(2) 0.006(2) C32 0.049(2) 0.078(3) 0.044(2) -0.0073(18) 0.0004(17) 0.0054(18) C33 0.051(2) 0.073(2) 0.042(2) -0.0077(17) 0.0034(17) 0.0058(17) C34 0.0404(19) 0.073(2) 0.047(2) -0.0091(17) 0.0031(16) 0.0073(16) C35 0.050(2) 0.089(3) 0.051(2) -0.0073(19) 0.0040(17) 0.0091(19) C36 0.046(2) 0.076(3) 0.051(2) -0.0070(18) -0.0032(17) 0.0069(17) C37 0.052(2) 0.094(3) 0.046(2) -0.0061(19) -0.0001(18) 0.0089(19) C38 0.050(2) 0.110(3) 0.047(2) -0.010(2) 0.0016(18) 0.007(2) C39 0.092(3) 0.147(5) 0.051(3) 0.016(3) 0.013(2) 0.020(3) C40 0.113(5) 0.216(8) 0.065(4) 0.030(4) 0.021(3) 0.041(5) C41 0.068(3) 0.279(10) 0.059(4) -0.029(5) 0.012(3) 0.019(5) C42 0.108(5) 0.216(8) 0.102(5) -0.088(5) 0.037(4) -0.026(5) C43 0.082(3) 0.150(5) 0.088(3) -0.050(3) 0.031(3) -0.022(3) C44 0.045(2) 0.079(3) 0.047(2) -0.0073(19) -0.0036(16) 0.0107(19) C45 0.052(2) 0.078(3) 0.062(2) 0.000(2) -0.0050(19) 0.004(2) C46 0.082(3) 0.073(3) 0.101(3) 0.000(3) -0.020(3) -0.007(2) C47 0.104(4) 0.073(3) 0.133(4) 0.014(3) -0.035(3) -0.002(3) C48 0.088(3) 0.075(3) 0.085(3) 0.007(2) -0.014(2) 0.009(3) C49 0.097(4) 0.095(4) 0.187(6) -0.006(4) -0.048(4) -0.027(3) C50 0.116(4) 0.095(4) 0.116(4) 0.016(3) -0.040(3) 0.023(3) C51 0.054(2) 0.069(3) 0.050(2) -0.0075(19) -0.0072(17) 0.0098(19) C52 0.084(3) 0.071(3) 0.075(3) -0.010(2) -0.019(2) 0.017(2) C53 0.112(4) 0.065(3) 0.112(4) -0.008(3) -0.035(3) 0.004(3) C54 0.080(3) 0.074(3) 0.085(3) -0.012(2) -0.026(2) 0.000(2) C55 0.112(4) 0.077(3) 0.105(4) 0.003(3) -0.038(3) 0.020(3) C56 0.102(4) 0.097(4) 0.125(4) -0.014(3) -0.041(3) -0.015(3) Cl1 0.1517(14) 0.1406(14) 0.1278(12) -0.0057(10) -0.0081(10) 0.0588(11) Cl2 0.1699(18) 0.1620(18) 0.218(2) 0.0429(15) 0.0244(15) -0.0757(15) Cl3 0.242(2) 0.1187(13) 0.1350(14) 0.0469(11) 0.0576(14) 0.0184(12) Cl4 0.260(2) 0.1221(13) 0.208(2) -0.0844(13) 0.1415(19) -0.0627(14) F1 0.0539(12) 0.0890(15) 0.0667(13) 0.0043(11) 0.0112(10) 0.0035(11) F2 0.0703(15) 0.0787(15) 0.0945(16) -0.0080(12) -0.0076(12) 0.0158(12) F3 0.0429(13) 0.150(2) 0.0983(18) 0.0003(16) -0.0069(12) -0.0033(13) F4 0.0908(17) 0.134(2) 0.0566(15) 0.0044(13) -0.0160(12) -0.0045(15) F5 0.0737(16) 0.126(2) 0.0643(14) 0.0059(14) 0.0126(12) -0.0081(13) F6 0.0692(15) 0.1102(19) 0.0886(16) -0.0393(14) 0.0012(12) 0.0210(13) F7 0.0516(14) 0.1037(18) 0.136(2) 0.0124(16) -0.0130(13) 0.0052(12) F8 0.127(2) 0.122(2) 0.0465(14) -0.0042(13) -0.0184(13) 0.0038(16) N1 0.0467(18) 0.103(3) 0.0486(19) -0.0133(17) 0.0023(14) 0.0072(16) N2 0.0358(16) 0.093(2) 0.0467(17) 0.0016(15) -0.0039(14) -0.0004(14) N3 0.058(2) 0.089(3) 0.065(2) 0.0060(18) -0.0152(16) 0.0073(18) N4 0.0482(17) 0.080(2) 0.0544(18) 0.0000(16) -0.0067(14) -0.0130(16) N5 0.0447(17) 0.084(2) 0.0545(19) -0.0091(15) 0.0017(14) 0.0110(15) N6 0.0424(16) 0.085(2) 0.0416(16) -0.0072(14) -0.0003(14) 0.0087(14) N7 0.0571(19) 0.069(2) 0.0580(19) 0.0030(16) -0.0065(15) 0.0069(15) N8 0.0575(19) 0.071(2) 0.0522(18) -0.0077(15) -0.0102(15) 0.0041(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 B1 F2 1.375(5) . ? B1 F1 1.379(5) . ? B1 N2 1.534(5) . ? B1 N1 1.540(5) . ? B2 F4 1.376(5) . ? B2 F3 1.394(5) . ? B2 N3 1.529(6) . ? B2 N4 1.532(6) . ? B3 F6 1.373(5) . ? B3 F5 1.376(5) . ? B3 N6 1.533(5) . ? B3 N5 1.543(5) . ? B4 F7 1.374(5) . ? B4 F8 1.391(5) . ? B4 N7 1.518(5) . ? B4 N8 1.539(5) . ? C1 N1 1.332(5) . ? C1 C2 1.399(6) . ? C2 C3 1.354(5) . ? C3 C4 1.396(5) . ? C4 C5 1.386(5) . ? C4 N1 1.387(4) . ? C5 C6 1.387(5) . ? C5 C10 1.490(5) . ? C6 N2 1.393(4) . ? C6 C7 1.403(5) . ? C7 C8 1.389(5) . ? C8 C9 1.387(5) . ? C8 C22 1.479(5) . ? C9 N2 1.345(4) . ? C10 C15 1.379(7) . ? C10 C11 1.397(7) . ? C11 C12 1.417(7) . ? C11 Cl1 1.698(7) . ? C12 C13 1.355(13) . ? C13 C14 1.305(14) . ? C14 C15 1.398(8) . ? C15 Cl2 1.738(7) . ? C16 C22 1.381(5) . ? C16 N4 1.404(4) . ? C16 C17 1.434(5) . ? C17 C18 1.376(6) . ? C17 C20 1.486(6) . ? C18 C19 1.385(6) . ? C19 N4 1.350(5) . ? C19 C21 1.490(6) . ? C22 C23 1.395(5) . ? C23 N3 1.400(5) . ? C23 C24 1.422(6) . ? C24 C25 1.357(6) . ? C24 C27 1.495(6) . ? C25 C26 1.394(6) . ? C26 N3 1.353(5) . ? C26 C28 1.495(6) . ? C29 N5 1.337(4) . ? C29 C30 1.382(5) . ? C30 C31 1.363(5) . ? C31 C32 1.404(5) . ? C32 N5 1.381(4) . ? C32 C33 1.383(5) . ? C33 C34 1.395(5) . ? C33 C38 1.484(5) . ? C34 N6 1.384(4) . ? C34 C35 1.399(4) . ? C35 C36 1.377(5) . ? C36 C37 1.394(5) . ? C36 C44 1.481(5) . ? C37 N6 1.324(4) . ? C38 C43 1.377(6) . ? C38 C39 1.381(6) . ? C39 C40 1.371(7) . ? C39 Cl3 1.755(6) . ? C40 C41 1.336(9) . ? C41 C42 1.348(9) . ? C42 C43 1.389(7) . ? C43 Cl4 1.719(6) . ? C44 C51 1.391(5) . ? C44 C45 1.398(5) . ? C45 N7 1.401(4) . ? C45 C46 1.419(5) . ? C46 C47 1.371(6) . ? C46 C49 1.505(6) . ? C47 C48 1.382(6) . ? C48 N7 1.352(5) . ? C48 C50 1.497(6) . ? C51 N8 1.399(4) . ? C51 C52 1.420(5) . ? C52 C53 1.359(6) . ? C52 C55 1.509(5) . ? C53 C54 1.393(6) . ? C54 N8 1.342(5) . ? C54 C56 1.501(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 F2 B1 F1 108.5(3) . . ? F2 B1 N2 110.2(3) . . ? F1 B1 N2 110.9(3) . . ? F2 B1 N1 110.9(3) . . ? F1 B1 N1 110.7(3) . . ? N2 B1 N1 105.7(3) . . ? F4 B2 F3 109.6(3) . . ? F4 B2 N3 110.8(4) . . ? F3 B2 N3 109.7(4) . . ? F4 B2 N4 110.5(3) . . ? F3 B2 N4 109.3(3) . . ? N3 B2 N4 107.0(3) . . ? F6 B3 F5 108.7(3) . . ? F6 B3 N6 110.4(3) . . ? F5 B3 N6 110.2(3) . . ? F6 B3 N5 111.2(3) . . ? F5 B3 N5 110.2(3) . . ? N6 B3 N5 106.2(3) . . ? F7 B4 F8 109.4(3) . . ? F7 B4 N7 111.2(3) . . ? F8 B4 N7 110.0(3) . . ? F7 B4 N8 110.1(3) . . ? F8 B4 N8 109.2(3) . . ? N7 B4 N8 106.8(3) . . ? N1 C1 C2 110.9(4) . . ? C3 C2 C1 106.2(4) . . ? C2 C3 C4 108.1(3) . . ? C5 C4 N1 120.0(3) . . ? C5 C4 C3 131.9(3) . . ? N1 C4 C3 108.1(3) . . ? C4 C5 C6 121.6(3) . . ? C4 C5 C10 117.9(3) . . ? C6 C5 C10 120.5(3) . . ? C5 C6 N2 119.6(3) . . ? C5 C6 C7 132.1(3) . . ? N2 C6 C7 108.1(3) . . ? C8 C7 C6 107.3(3) . . ? C9 C8 C7 106.6(3) . . ? C9 C8 C22 122.6(3) . . ? C7 C8 C22 130.6(3) . . ? N2 C9 C8 110.9(3) . . ? C15 C10 C11 117.9(5) . . ? C15 C10 C5 121.2(5) . . ? C11 C10 C5 120.9(4) . . ? C10 C11 C12 118.4(7) . . ? C10 C11 Cl1 119.6(4) . . ? C12 C11 Cl1 122.0(6) . . ? C13 C12 C11 121.3(8) . . ? C14 C13 C12 120.1(8) . . ? C13 C14 C15 121.6(10) . . ? C10 C15 C14 120.7(7) . . ? C10 C15 Cl2 118.7(4) . . ? C14 C15 Cl2 120.6(6) . . ? C22 C16 N4 119.8(3) . . ? C22 C16 C17 132.0(4) . . ? N4 C16 C17 108.1(3) . . ? C18 C17 C16 104.7(4) . . ? C18 C17 C20 125.7(4) . . ? C16 C17 C20 129.6(4) . . ? C17 C18 C19 110.5(4) . . ? N4 C19 C18 108.6(4) . . ? N4 C19 C21 122.8(4) . . ? C18 C19 C21 128.6(5) . . ? C16 C22 C23 121.3(3) . . ? C16 C22 C8 122.1(3) . . ? C23 C22 C8 116.5(4) . . ? C22 C23 N3 120.4(4) . . ? C22 C23 C24 132.0(4) . . ? N3 C23 C24 107.5(3) . . ? C25 C24 C23 106.3(4) . . ? C25 C24 C27 123.9(5) . . ? C23 C24 C27 129.7(4) . . ? C24 C25 C26 109.9(4) . . ? N3 C26 C25 108.0(4) . . ? N3 C26 C28 123.3(5) . . ? C25 C26 C28 128.7(5) . . ? N5 C29 C30 110.5(4) . . ? C31 C30 C29 107.6(4) . . ? C30 C31 C32 106.6(3) . . ? N5 C32 C33 120.5(3) . . ? N5 C32 C31 108.6(3) . . ? C33 C32 C31 130.9(3) . . ? C32 C33 C34 121.0(3) . . ? C32 C33 C38 118.2(3) . . ? C34 C33 C38 120.8(3) . . ? N6 C34 C33 120.3(3) . . ? N6 C34 C35 108.4(3) . . ? C33 C34 C35 131.3(3) . . ? C36 C35 C34 107.5(3) . . ? C35 C36 C37 105.6(3) . . ? C35 C36 C44 129.0(3) . . ? C37 C36 C44 125.4(3) . . ? N6 C37 C36 111.8(3) . . ? C43 C38 C39 116.3(4) . . ? C43 C38 C33 122.1(4) . . ? C39 C38 C33 121.5(4) . . ? C40 C39 C38 122.9(6) . . ? C40 C39 Cl3 119.0(5) . . ? C38 C39 Cl3 118.0(3) . . ? C41 C40 C39 119.3(7) . . ? C40 C41 C42 120.3(6) . . ? C41 C42 C43 120.9(6) . . ? C38 C43 C42 120.2(6) . . ? C38 C43 Cl4 118.8(3) . . ? C42 C43 Cl4 121.0(5) . . ? C51 C44 C45 121.3(3) . . ? C51 C44 C36 119.1(3) . . ? C45 C44 C36 119.5(3) . . ? C44 C45 N7 119.3(3) . . ? C44 C45 C46 132.4(4) . . ? N7 C45 C46 108.2(3) . . ? C47 C46 C45 105.4(4) . . ? C47 C46 C49 126.0(4) . . ? C45 C46 C49 128.5(4) . . ? C46 C47 C48 110.0(4) . . ? N7 C48 C47 108.6(4) . . ? N7 C48 C50 122.9(4) . . ? C47 C48 C50 128.5(4) . . ? C44 C51 N8 120.2(3) . . ? C44 C51 C52 132.3(3) . . ? N8 C51 C52 107.3(3) . . ? C53 C52 C51 106.7(4) . . ? C53 C52 C55 124.4(4) . . ? C51 C52 C55 128.9(4) . . ? C52 C53 C54 108.9(4) . . ? N8 C54 C53 109.0(4) . . ? N8 C54 C56 122.9(4) . . ? C53 C54 C56 128.2(4) . . ? C1 N1 C4 106.6(3) . . ? C1 N1 B1 127.1(3) . . ? C4 N1 B1 126.2(3) . . ? C9 N2 C6 107.1(3) . . ? C9 N2 B1 126.1(3) . . ? C6 N2 B1 126.6(3) . . ? C26 N3 C23 108.2(4) . . ? C26 N3 B2 127.6(4) . . ? C23 N3 B2 124.0(3) . . ? C19 N4 C16 108.0(3) . . ? C19 N4 B2 127.0(3) . . ? C16 N4 B2 124.4(3) . . ? C29 N5 C32 106.7(3) . . ? C29 N5 B3 127.3(3) . . ? C32 N5 B3 125.9(3) . . ? C37 N6 C34 106.7(3) . . ? C37 N6 B3 127.3(3) . . ? C34 N6 B3 126.0(3) . . ? C48 N7 C45 107.7(3) . . ? C48 N7 B4 126.3(3) . . ? C45 N7 B4 125.3(3) . . ? C54 N8 C51 108.1(3) . . ? C54 N8 B4 127.4(3) . . ? C51 N8 B4 124.5(3) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.56 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.736 _refine_diff_density_min -0.683 _refine_diff_density_rms 0.046