Supplementary Material for Chemical Communications This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Pi-Tai Chou' 'Chung-Chih Cheng' 'Yun Chi' 'Gene-Hsiang Lee' 'Shie-Ming Peng' 'Yi-Hwa Song' 'Pei-Chi Wu' 'Wei-Shan Yu' _publ_contact_author_name 'Prof Pi-Tai Chou' _publ_contact_author_address ; Department of Chemistry National Taiwan University Taipei 106 TAIWAN ; _publ_contact_author_email CHOP@CCMS.NTU.EDU.TW _publ_requested_journal 'Chemical Communications' _publ_section_title ; Syntheses and Remarkable Photophysical Properties of 2-(2-Pyridyl) Pyrazolate Boron Complexes; Photoinduced Electron Transfer ; data_ic8899 _database_code_CSD 201833 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H15 B F3 N3' _chemical_formula_weight 377.17 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 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 9.2385(5) _cell_length_b 11.4876(6) _cell_length_c 17.0928(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1814.03(17) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3782 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 22.15 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.381 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 SMART APEX 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 14266 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4153 _reflns_number_gt 3680 _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^)+(0.0694P)^2^+0.0761P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.3(9) _refine_ls_number_reflns 4153 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0541 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.1244 _refine_ls_wR_factor_gt 0.1204 _refine_ls_goodness_of_fit_ref 1.093 _refine_ls_restrained_S_all 1.093 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.3968(2) 0.49463(17) 0.19307(11) 0.0413(4) Uani 1 1 d . . . N1 N 0.38207(16) 0.46521(13) 0.28598(8) 0.0431(3) Uani 1 1 d . . . N2 N 0.29929(16) 0.60623(12) 0.19887(8) 0.0416(3) Uani 1 1 d . . . N3 N 0.25291(18) 0.68168(13) 0.14496(9) 0.0466(4) Uani 1 1 d . . . C1 C 0.4384(3) 0.37339(18) 0.32254(12) 0.0553(5) Uani 1 1 d . . . H1A H 0.4933 0.3199 0.2944 0.066 Uiso 1 1 calc R . . C2 C 0.4165(3) 0.3567(2) 0.40104(14) 0.0658(6) Uani 1 1 d . . . H2A H 0.4567 0.2926 0.4262 0.079 Uiso 1 1 calc R . . C3 C 0.3351(3) 0.4349(2) 0.44200(13) 0.0666(6) Uani 1 1 d . . . H3A H 0.3180 0.4232 0.4950 0.080 Uiso 1 1 calc R . . C4 C 0.2777(2) 0.5316(2) 0.40505(12) 0.0585(5) Uani 1 1 d . . . H4A H 0.2245 0.5866 0.4328 0.070 Uiso 1 1 calc R . . C5 C 0.30182(19) 0.54436(16) 0.32533(11) 0.0458(4) Uani 1 1 d . . . C6 C 0.2527(2) 0.63272(16) 0.27069(11) 0.0443(4) Uani 1 1 d . . . C7 C 0.1703(2) 0.73263(18) 0.26560(13) 0.0555(5) Uani 1 1 d . . . H7A H 0.1239 0.7732 0.3055 0.067 Uiso 1 1 calc R . . C8 C 0.1737(2) 0.75747(16) 0.18643(12) 0.0500(4) Uani 1 1 d . . . C9 C 0.1021(3) 0.8552(2) 0.14500(16) 0.0685(6) Uani 1 1 d . . . C10 C 0.55968(19) 0.52779(15) 0.17136(11) 0.0441(4) Uani 1 1 d . . . C11 C 0.6581(3) 0.5677(2) 0.22627(14) 0.0643(6) Uani 1 1 d . . . H11A H 0.6301 0.5715 0.2785 0.077 Uiso 1 1 calc R . . C12 C 0.7966(3) 0.6020(3) 0.20592(19) 0.0829(8) Uani 1 1 d . . . H12A H 0.8600 0.6287 0.2442 0.099 Uiso 1 1 calc R . . C13 C 0.8403(3) 0.5968(2) 0.12965(19) 0.0760(7) Uani 1 1 d . . . H13A H 0.9340 0.6183 0.1160 0.091 Uiso 1 1 calc R . . C14 C 0.7460(3) 0.5599(2) 0.07394(16) 0.0755(7) Uani 1 1 d . . . H14A H 0.7750 0.5567 0.0219 0.091 Uiso 1 1 calc R . . C15 C 0.6067(2) 0.5271(2) 0.09431(13) 0.0592(5) Uani 1 1 d . . . H15A H 0.5429 0.5039 0.0552 0.071 Uiso 1 1 calc R . . C16 C 0.3215(2) 0.39239(15) 0.14321(10) 0.0424(4) Uani 1 1 d . . . C17 C 0.1746(2) 0.3947(2) 0.12611(11) 0.0531(5) Uani 1 1 d . . . H17A H 0.1187 0.4568 0.1437 0.064 Uiso 1 1 calc R . . C18 C 0.1097(3) 0.3065(2) 0.08339(13) 0.0669(6) Uani 1 1 d . . . H18A H 0.0116 0.3107 0.0715 0.080 Uiso 1 1 calc R . . C19 C 0.1898(3) 0.2128(2) 0.05864(14) 0.0729(7) Uani 1 1 d . . . H19A H 0.1459 0.1535 0.0302 0.088 Uiso 1 1 calc R . . C20 C 0.3344(3) 0.2068(2) 0.07583(14) 0.0676(6) Uani 1 1 d . . . H20A H 0.3886 0.1429 0.0599 0.081 Uiso 1 1 calc R . . C21 C 0.3995(2) 0.29680(17) 0.11715(12) 0.0543(5) Uani 1 1 d . . . H21A H 0.4981 0.2928 0.1276 0.065 Uiso 1 1 calc R . . F1 F 0.0401(2) 0.82381(14) 0.07832(10) 0.0900(5) Uani 1 1 d . . . F2 F 0.1939(2) 0.94070(12) 0.12604(11) 0.0982(6) Uani 1 1 d . . . F3 F 0.0009(2) 0.90370(18) 0.18972(12) 0.1199(7) 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 0.0501(10) 0.0363(9) 0.0376(9) -0.0020(8) -0.0021(8) 0.0042(8) N1 0.0479(8) 0.0407(8) 0.0407(7) -0.0024(6) -0.0042(6) -0.0026(7) N2 0.0468(8) 0.0387(7) 0.0392(7) -0.0023(6) -0.0009(6) 0.0017(6) N3 0.0509(8) 0.0430(8) 0.0460(8) 0.0033(6) -0.0033(7) 0.0016(7) C1 0.0693(13) 0.0452(10) 0.0515(11) 0.0007(9) -0.0087(10) 0.0022(10) C2 0.0874(17) 0.0541(12) 0.0559(12) 0.0112(10) -0.0140(12) -0.0065(12) C3 0.0820(16) 0.0770(15) 0.0409(10) 0.0098(10) -0.0026(10) -0.0148(13) C4 0.0652(13) 0.0678(13) 0.0424(10) -0.0066(9) 0.0025(9) -0.0028(11) C5 0.0468(9) 0.0477(10) 0.0428(9) -0.0041(8) -0.0011(8) -0.0076(8) C6 0.0445(9) 0.0458(9) 0.0426(9) -0.0071(7) 0.0009(8) -0.0021(8) C7 0.0569(11) 0.0549(11) 0.0548(11) -0.0107(9) 0.0041(9) 0.0100(10) C8 0.0469(10) 0.0435(9) 0.0596(12) -0.0020(8) -0.0047(9) 0.0035(8) C9 0.0757(15) 0.0541(12) 0.0758(15) 0.0024(11) -0.0122(13) 0.0129(11) C10 0.0454(9) 0.0362(8) 0.0508(10) -0.0031(7) -0.0028(8) 0.0031(7) C11 0.0635(13) 0.0701(13) 0.0593(13) 0.0029(11) -0.0099(11) -0.0125(11) C12 0.0610(14) 0.0895(19) 0.098(2) 0.0167(16) -0.0258(14) -0.0231(13) C13 0.0467(11) 0.0695(15) 0.112(2) 0.0093(15) 0.0041(13) -0.0059(10) C14 0.0676(14) 0.0737(15) 0.0851(18) -0.0095(13) 0.0266(14) -0.0100(13) C15 0.0574(11) 0.0623(12) 0.0577(11) -0.0139(10) 0.0076(10) -0.0100(10) C16 0.0495(10) 0.0420(9) 0.0358(8) -0.0010(7) -0.0004(7) -0.0044(8) C17 0.0524(11) 0.0614(12) 0.0457(10) -0.0002(9) 0.0016(9) -0.0056(9) C18 0.0663(13) 0.0819(16) 0.0527(11) 0.0025(11) -0.0092(11) -0.0256(13) C19 0.102(2) 0.0654(15) 0.0517(12) -0.0110(11) 0.0003(13) -0.0351(14) C20 0.0946(18) 0.0448(11) 0.0633(14) -0.0121(10) 0.0134(12) -0.0085(12) C21 0.0608(11) 0.0432(10) 0.0590(11) -0.0066(9) 0.0032(10) -0.0009(9) F1 0.1000(11) 0.0759(10) 0.0941(11) 0.0119(8) -0.0402(9) 0.0054(8) F2 0.1304(14) 0.0507(8) 0.1134(13) 0.0169(8) -0.0289(11) -0.0113(9) F3 0.1206(15) 0.1170(14) 0.1222(15) 0.0145(12) 0.0103(13) 0.0777(13) _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 N2 1.570(2) . ? B1 C10 1.596(3) . ? B1 C16 1.609(3) . ? B1 N1 1.629(2) . ? N1 C1 1.332(2) . ? N1 C5 1.352(2) . ? N2 N3 1.336(2) . ? N2 C6 1.336(2) . ? N3 C8 1.340(2) . ? C1 C2 1.371(3) . ? C2 C3 1.365(4) . ? C3 C4 1.383(3) . ? C4 C5 1.388(3) . ? C5 C6 1.452(3) . ? C6 C7 1.380(3) . ? C7 C8 1.383(3) . ? C8 C9 1.483(3) . ? C9 F1 1.326(3) . ? C9 F3 1.330(3) . ? C9 F2 1.337(3) . ? C10 C11 1.384(3) . ? C10 C15 1.387(3) . ? C11 C12 1.384(4) . ? C12 C13 1.366(4) . ? C13 C14 1.359(4) . ? C14 C15 1.385(3) . ? C16 C21 1.387(3) . ? C16 C17 1.388(3) . ? C17 C18 1.386(3) . ? C18 C19 1.373(4) . ? C19 C20 1.369(4) . ? C20 C21 1.389(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 N2 B1 C10 111.15(15) . . ? N2 B1 C16 112.41(15) . . ? C10 B1 C16 117.30(15) . . ? N2 B1 N1 93.43(13) . . ? C10 B1 N1 110.80(15) . . ? C16 B1 N1 109.18(14) . . ? C1 N1 C5 120.88(16) . . ? C1 N1 B1 126.08(16) . . ? C5 N1 B1 113.03(15) . . ? N3 N2 C6 112.50(15) . . ? N3 N2 B1 132.10(14) . . ? C6 N2 B1 115.40(14) . . ? N2 N3 C8 103.40(15) . . ? N1 C1 C2 120.8(2) . . ? C3 C2 C1 119.4(2) . . ? C2 C3 C4 120.4(2) . . ? C3 C4 C5 118.1(2) . . ? N1 C5 C4 120.36(19) . . ? N1 C5 C6 108.75(16) . . ? C4 C5 C6 130.89(19) . . ? N2 C6 C7 108.02(17) . . ? N2 C6 C5 109.33(16) . . ? C7 C6 C5 142.59(18) . . ? C6 C7 C8 102.73(17) . . ? N3 C8 C7 113.33(18) . . ? N3 C8 C9 118.9(2) . . ? C7 C8 C9 127.80(19) . . ? F1 C9 F3 107.7(2) . . ? F1 C9 F2 105.4(2) . . ? F3 C9 F2 106.1(2) . . ? F1 C9 C8 113.43(19) . . ? F3 C9 C8 110.9(2) . . ? F2 C9 C8 112.9(2) . . ? C11 C10 C15 116.11(19) . . ? C11 C10 B1 122.70(18) . . ? C15 C10 B1 120.99(17) . . ? C10 C11 C12 122.1(2) . . ? C13 C12 C11 120.0(3) . . ? C14 C13 C12 119.5(2) . . ? C13 C14 C15 120.3(2) . . ? C10 C15 C14 121.9(2) . . ? C21 C16 C17 117.09(18) . . ? C21 C16 B1 121.57(17) . . ? C17 C16 B1 121.32(17) . . ? C18 C17 C16 121.3(2) . . ? C19 C18 C17 120.1(2) . . ? C20 C19 C18 119.9(2) . . ? C19 C20 C21 119.6(2) . . ? C16 C21 C20 121.8(2) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.212 _refine_diff_density_min -0.153 _refine_diff_density_rms 0.033 #===END