# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Mark E. Thompson' _publ_contact_author_address ;University of Southern California Los Angeles, CA 90089 ; _publ_contact_author_email met@usc.edu _publ_contact_author_phone 213-740-5704 _publ_contact_author_fax 213-740-8594 loop_ _publ_author_name _publ_author_address 'Whited, Matthew T.' ;University of Southern California Los Angeles, CA 90089 ; 'Patel, Niral' ;University of Southern California Los Angeles, CA 90089 ; 'Roberts, Sean T.' ;University of Southern California Los Angeles, CA 90089 ; 'Djurovich, Peter I.' ;University of Southern California Los Angeles, CA 90089 ; 'Bradforth, Stephen E.' ;University of Southern California Los Angeles, CA 90089 ; 'Thompson, Mark E.' ;University of Southern California Los Angeles, CA 90089 ; data_mtw04 _database_code_depnum_ccdc_archive 'CCDC 820543' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H24 B2 F4 N4' _chemical_formula_sum 'C28 H24 B2 F4 N4' _chemical_formula_weight 514.13 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 Orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall -P2ac2ab 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' '-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 12.808(3) _cell_length_b 12.205(2) _cell_length_c 15.019(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2347.8(8) _cell_formula_units_Z 4 _cell_measurement_temperature 105(2) _cell_measurement_reflns_used 1442 _cell_measurement_theta_min 2.6732 _cell_measurement_theta_max 23.1621 _exptl_crystal_description prism _exptl_crystal_colour red _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 0.108 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5788 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 105(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 'Bruker APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13598 _diffrn_reflns_av_R_equivalents 0.1065 _diffrn_reflns_av_sigmaI/netI 0.1070 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.55 _reflns_number_total 2688 _reflns_number_gt 1506 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT, SADABS and XPREP' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2688 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1215 _refine_ls_R_factor_gt 0.0571 _refine_ls_wR_factor_ref 0.0926 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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 0.12894(19) 0.8049(2) 0.34245(15) 0.0250(6) Uani 1 1 d . . . F1 F 0.19443(8) 0.86431(10) 0.39880(7) 0.0350(4) Uani 1 1 d . . . F2 F 0.10368(9) 0.70658(10) 0.38305(7) 0.0351(4) Uani 1 1 d . . . N1 N 0.18200(12) 0.78565(14) 0.25183(10) 0.0233(4) Uani 1 1 d . . . N2 N 0.02940(11) 0.87256(15) 0.32392(10) 0.0220(4) Uani 1 1 d . . . C1 C 0.32774(16) 0.66706(19) 0.30759(14) 0.0356(6) Uani 1 1 d . . . H1A H 0.3421 0.7186 0.3543 0.053 Uiso 1 1 calc R . . H1B H 0.3923 0.6403 0.2835 0.053 Uiso 1 1 calc R . . H1C H 0.2882 0.6068 0.3311 0.053 Uiso 1 1 calc R . . C2 C 0.26671(15) 0.72209(18) 0.23596(13) 0.0260(5) Uani 1 1 d . . . C3 C 0.28491(16) 0.71842(18) 0.14447(13) 0.0282(5) Uani 1 1 d . . . H3 H 0.3384 0.6802 0.1164 0.034 Uiso 1 1 calc R . . C4 C 0.21037(15) 0.78097(18) 0.10302(13) 0.0249(5) Uani 1 1 d . . . H4 H 0.2037 0.7921 0.0420 0.030 Uiso 1 1 calc R . . C5 C 0.14591(15) 0.82517(17) 0.16966(13) 0.0218(5) Uani 1 1 d . . . C6 C 0.06072(14) 0.89670(18) 0.16521(12) 0.0207(5) Uani 1 1 d . . . C7 C 0.00414(14) 0.92198(17) 0.24247(13) 0.0225(5) Uani 1 1 d . . . C8 C -0.07999(14) 0.99379(18) 0.25739(13) 0.0241(5) Uani 1 1 d . . . H8 H -0.1118 1.0384 0.2152 0.029 Uiso 1 1 calc R . . C9 C -0.10643(16) 0.98592(19) 0.34550(13) 0.0280(6) Uani 1 1 d . . . H9 H -0.1599 1.0239 0.3738 0.034 Uiso 1 1 calc R . . C10 C -0.03874(15) 0.91054(18) 0.38549(13) 0.0250(5) Uani 1 1 d . . . C11 C -0.03720(16) 0.8715(2) 0.47979(13) 0.0317(6) Uani 1 1 d . . . H11A H -0.0538 0.7949 0.4815 0.048 Uiso 1 1 calc R . . H11B H -0.0878 0.9117 0.5138 0.048 Uiso 1 1 calc R . . H11C H 0.0310 0.8830 0.5046 0.048 Uiso 1 1 calc R . . C12 C 0.02965(15) 0.94788(17) 0.07959(12) 0.0221(5) Uani 1 1 d . . . C13 C 0.10332(15) 0.99738(17) 0.02459(12) 0.0211(5) Uani 1 1 d . . . H13 H 0.1734 0.9951 0.0405 0.025 Uiso 1 1 calc R . . C14 C 0.07475(15) 1.04948(17) -0.05268(13) 0.0221(5) Uani 1 1 d . . . H14 H 0.1254 1.0834 -0.0875 0.027 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 0.0291(14) 0.0246(16) 0.0213(14) 0.0025(12) -0.0054(11) -0.0032(13) F1 0.0299(7) 0.0465(9) 0.0287(7) -0.0079(6) -0.0059(5) -0.0006(6) F2 0.0464(8) 0.0295(8) 0.0294(7) 0.0076(6) 0.0035(6) 0.0045(7) N1 0.0255(9) 0.0233(11) 0.0212(10) -0.0016(9) -0.0018(8) 0.0014(9) N2 0.0223(9) 0.0257(11) 0.0179(10) 0.0008(8) 0.0001(8) 0.0000(9) C1 0.0306(13) 0.0372(17) 0.0391(14) 0.0023(12) -0.0035(10) 0.0065(12) C2 0.0243(12) 0.0228(13) 0.0311(13) 0.0008(11) -0.0014(10) 0.0006(11) C3 0.0302(12) 0.0231(13) 0.0312(13) -0.0035(11) 0.0047(10) 0.0003(11) C4 0.0275(11) 0.0249(14) 0.0224(11) -0.0008(10) 0.0012(9) -0.0016(11) C5 0.0266(12) 0.0212(13) 0.0177(11) 0.0020(10) -0.0009(9) -0.0028(11) C6 0.0194(11) 0.0208(12) 0.0219(12) -0.0013(10) -0.0029(9) -0.0039(10) C7 0.0230(11) 0.0246(13) 0.0200(12) 0.0017(10) -0.0046(9) -0.0021(10) C8 0.0227(12) 0.0274(14) 0.0220(12) 0.0017(10) -0.0029(9) 0.0007(10) C9 0.0240(12) 0.0341(15) 0.0259(13) -0.0040(11) 0.0015(10) 0.0041(11) C10 0.0235(11) 0.0291(14) 0.0225(12) -0.0010(11) 0.0016(9) -0.0049(11) C11 0.0352(13) 0.0360(15) 0.0239(12) 0.0025(11) -0.0001(10) -0.0031(12) C12 0.0247(11) 0.0230(13) 0.0186(12) -0.0015(10) 0.0012(9) 0.0012(11) C13 0.0177(11) 0.0238(13) 0.0218(11) -0.0050(10) -0.0043(9) 0.0015(10) C14 0.0253(12) 0.0235(13) 0.0176(11) -0.0013(10) 0.0004(9) -0.0045(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 F2 1.384(3) . ? B1 F1 1.395(3) . ? B1 N1 1.539(3) . ? B1 N2 1.544(3) . ? N1 C2 1.355(2) . ? N1 C5 1.403(2) . ? N2 C10 1.353(2) . ? N2 C7 1.402(2) . ? C1 C2 1.490(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C3 1.394(3) . ? C3 C4 1.372(3) . ? C3 H3 0.9300 . ? C4 C5 1.405(3) . ? C4 H4 0.9300 . ? C5 C6 1.399(3) . ? C6 C7 1.403(3) . ? C6 C12 1.484(3) . ? C7 C8 1.407(3) . ? C8 C9 1.369(3) . ? C8 H8 0.9300 . ? C9 C10 1.400(3) . ? C9 H9 0.9300 . ? C10 C11 1.494(3) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.392(3) . ? C12 C14 1.397(2) 5_575 ? C13 C14 1.373(3) . ? C13 H13 0.9300 . ? C14 C12 1.397(2) 5_575 ? C14 H14 0.9300 . ? 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 108.91(18) . . ? F2 B1 N1 111.15(19) . . ? F1 B1 N1 110.50(18) . . ? F2 B1 N2 110.49(18) . . ? F1 B1 N2 109.11(19) . . ? N1 B1 N2 106.66(16) . . ? C2 N1 C5 107.81(16) . . ? C2 N1 B1 126.61(17) . . ? C5 N1 B1 125.44(17) . . ? C10 N2 C7 107.46(17) . . ? C10 N2 B1 126.33(17) . . ? C7 N2 B1 125.30(16) . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N1 C2 C3 109.01(18) . . ? N1 C2 C1 123.45(18) . . ? C3 C2 C1 127.54(19) . . ? C4 C3 C2 108.24(19) . . ? C4 C3 H3 125.9 . . ? C2 C3 H3 125.9 . . ? C3 C4 C5 107.41(18) . . ? C3 C4 H4 126.3 . . ? C5 C4 H4 126.3 . . ? C6 C5 N1 120.90(17) . . ? C6 C5 C4 131.58(19) . . ? N1 C5 C4 107.51(18) . . ? C5 C6 C7 120.04(18) . . ? C5 C6 C12 120.88(17) . . ? C7 C6 C12 119.07(18) . . ? N2 C7 C6 120.54(18) . . ? N2 C7 C8 107.81(16) . . ? C6 C7 C8 131.64(18) . . ? C9 C8 C7 107.43(18) . . ? C9 C8 H8 126.3 . . ? C7 C8 H8 126.3 . . ? C8 C9 C10 107.92(18) . . ? C8 C9 H9 126.0 . . ? C10 C9 H9 126.0 . . ? N2 C10 C9 109.36(18) . . ? N2 C10 C11 122.00(19) . . ? C9 C10 C11 128.64(19) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C13 C12 C14 117.83(18) . 5_575 ? C13 C12 C6 121.01(18) . . ? C14 C12 C6 121.14(17) 5_575 . ? C14 C13 C12 121.47(18) . . ? C14 C13 H13 119.3 . . ? C12 C13 H13 119.3 . . ? C13 C14 C12 120.68(18) . 5_575 ? C13 C14 H14 119.7 . . ? C12 C14 H14 119.7 5_575 . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.285 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.053