# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/265 data_global # 1. SUBMISSION DETAILS _publ_contact_autor ; Dieter E. Kaufmann ; _publ_contact_author_phone '049 5323/722027' _publ_contact_author_fax '049 5323/722834' _publ_contact_author_email 'dieter.kaufmann@tu-clausthal.de' _publ_requested_journal 'JCS, Perk. Trans. 2, ...., 2000 ' #============================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Synthesis and Properties of Fluorescent Organoboranes: Dyes of the Triarylmethane Type ; loop_ _publ_author_name _publ_author_address 'Kaufmann, Dieter E.' ; Institut f\"ur Organische Chemie Technische Universit\"at Clausthal Leibnizstr. 6 38678 Clausthal-Zellerfeld Germany ; 'Albrecht,Karsten' ; Institut f\"ur Organische Chemie Technische Universit\"at Clausthal Leibnizstr. 6 38678 Clausthal-Zellerfeld Germany ; 'Kaiser, Volker' ; Institut f\"ur Anorganische und Analytische Chemie Technische Universit\"at Clausthal Paul-Ernst-Str. 4 38678 Clausthal-Zellerfeld Germany ; 'Boese, Roland' ; Institut f\"ur Anorganische Chemie Universit\"at-GH Essen Universit\"atsstr. 5-7 45117 Essen Germany ; 'Adams, J\"org' ; Institut f\"ur Physikalische Chemie Technische Universit\"at Clausthal Arnold-Sommerfeld-Str. 4 38678 Clausthal-Zellerfeld Germany ; #============================================================================= # 4. TEXT _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_experimental ; ; _publ_section_references ; Sheldrick, G. M.: SHELXL-93, a program for refining crystal structures. University of G\"ottingen. ; _publ_section_figure_captions ; ; _publ_section_acknowledgements ; ; data_alb4 _audit_creation_method SHELXL _chemical_name_systematic ; 2-(N,N-Dimethylaminophenyl)dimesitylboran ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C26 H32 B N' _chemical_formula_weight 369.34 _chemical_melting_point 144 _chemical_compound_source ? 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' _symmetry_cell_setting 'first setting, choice 1' _symmetry_space_group_name_H-M 'C2/c (No.15)' 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 28.728(20) _cell_length_b 9.7130(10) _cell_length_c 16.9970(10) _cell_angle_alpha 90.00 _cell_angle_beta 105.95(2) _cell_angle_gamma 90.00 _cell_volume 4560.2(32) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 8 _cell_measurement_theta_max 11 _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.076 _exptl_crystal_density_method ? _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_type 'not corrected' _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Enraf Nonius CAD4' _diffrn_measurement_method Omega-scans _diffrn_refln_scan_width 1.10 _diffrn_refln_scan_mode_backgd MO _diffrn_standards_number 2 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 8 _diffrn_reflns_number 5911 _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 1 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 30.03 _reflns_number_total 4459 _reflns_number_observed 1768 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'CAD4 EXPRESS' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4 (Harms, 1993)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1000P)^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 ? _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4458 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1844 _refine_ls_R_factor_obs 0.0744 _refine_ls_wR_factor_all 0.2454 _refine_ls_wR_factor_obs 0.2004 _refine_ls_goodness_of_fit_all 1.196 _refine_ls_goodness_of_fit_obs 1.613 _refine_ls_restrained_S_all 1.197 _refine_ls_restrained_S_obs 1.613 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group B1 B 0.12212(12) 0.1188(5) 0.1762(2) 0.0560(11) Uani 1 d . . N1 N 0.13998(12) -0.0955(3) 0.3127(2) 0.0893(10) Uani 1 d . . C1 C 0.11358(11) 0.2961(4) 0.0587(2) 0.0608(9) Uani 1 d . . C2 C 0.20503(11) 0.1732(4) 0.2827(2) 0.0596(9) Uani 1 d . . C3 C 0.09151(10) 0.2041(3) 0.1011(2) 0.0594(9) Uani 1 d . . C4 C 0.12196(10) -0.0406(4) 0.1673(2) 0.0626(11) Uani 1 d . . C5 C 0.15488(10) 0.1995(3) 0.2532(2) 0.0551(9) Uani 1 d . . C6 C 0.04091(11) 0.1858(4) 0.0702(2) 0.0681(10) Uani 1 d . . C7 C 0.13584(12) 0.3050(4) 0.2914(2) 0.0631(9) Uani 1 d . . C8 C 0.21444(14) 0.3547(4) 0.3840(2) 0.0697(10) Uani 1 d . . C9 C 0.01555(12) 0.2573(4) 0.0019(2) 0.0828(12) Uani 1 d . . H9 H -0.01770(12) 0.2436(4) -0.0171(2) 0.099 Uiso 1 calc R . C10 C 0.16566(14) 0.3776(4) 0.3562(2) 0.0741(11) Uani 1 d . . H10 H 0.15191(14) 0.4447(4) 0.3819(2) 0.089 Uiso 1 calc R . C11 C 0.23338(12) 0.2524(4) 0.3464(2) 0.0669(10) Uani 1 d . . H11 H 0.26646(12) 0.2351(4) 0.3642(2) 0.080 Uiso 1 calc R . C12 C 0.23035(11) 0.0635(4) 0.2473(2) 0.0815(12) Uani 1 d . . H12A H 0.20718(11) 0.0163(4) 0.2042(2) 0.122 Uiso 1 calc R . H12B H 0.24547(11) -0.0010(4) 0.2893(2) 0.122 Uiso 1 calc R . H12C H 0.25453(11) 0.1053(4) 0.2257(2) 0.122 Uiso 1 calc R . C13 C 0.16776(11) 0.3185(4) 0.0847(2) 0.0748(11) Uani 1 d . . H13A H 0.18203(11) 0.2638(4) 0.1322(2) 0.112 Uiso 1 calc R . H13B H 0.17453(11) 0.4140(4) 0.0973(2) 0.112 Uiso 1 calc R . H13C H 0.18112(11) 0.2919(4) 0.0410(2) 0.112 Uiso 1 calc R . C14 C 0.08623(12) 0.3665(4) -0.0093(2) 0.0739(10) Uani 1 d . . H14 H 0.10168(12) 0.4284(4) -0.0354(2) 0.089 Uiso 1 calc R . C15 C 0.13264(11) -0.1374(5) 0.2305(2) 0.0705(10) Uani 1 d . . C16 C 0.12137(13) -0.2285(6) 0.0718(3) 0.098(2) Uani 1 d . . H16 H 0.11799(13) -0.2580(6) 0.0185(3) 0.118 Uiso 1 calc R . C17 C 0.03696(14) 0.3479(4) -0.0396(2) 0.0849(12) Uani 1 d . . C18 C 0.01282(12) 0.0931(4) 0.1108(2) 0.0926(13) Uani 1 d . . H18A H 0.03455(12) 0.0496(4) 0.1573(2) 0.139 Uiso 1 calc R . H18B H -0.00346(12) 0.0240(4) 0.0728(2) 0.139 Uiso 1 calc R . H18C H -0.01062(12) 0.1464(4) 0.1285(2) 0.139 Uiso 1 calc R . C19 C 0.11599(11) -0.0907(5) 0.0881(2) 0.0786(12) Uani 1 d . . H19 H 0.10808(11) -0.0290(5) 0.0446(2) 0.094 Uiso 1 calc R . C20 C 0.08279(13) 0.3415(5) 0.2668(2) 0.0972(13) Uani 1 d . . H20A H 0.06603(13) 0.2847(5) 0.2217(2) 0.146 Uiso 1 calc R . H20B H 0.07896(13) 0.4365(5) 0.2509(2) 0.146 Uiso 1 calc R . H20C H 0.06961(13) 0.3264(5) 0.3123(2) 0.146 Uiso 1 calc R . C21 C 0.2466(2) 0.4380(4) 0.4531(2) 0.0976(14) Uani 1 d . . H21A H 0.2795(2) 0.4067(4) 0.4636(2) 0.146 Uiso 1 calc R . H21B H 0.2360(2) 0.4266(4) 0.5016(2) 0.146 Uiso 1 calc R . H21C H 0.2448(2) 0.5336(4) 0.4381(2) 0.146 Uiso 1 calc R . C22 C 0.13709(13) -0.2767(5) 0.2127(3) 0.0936(13) Uani 1 d . . H22 H 0.14390(13) -0.3407(5) 0.2550(3) 0.112 Uiso 1 calc R . C23 C 0.0078(2) 0.4224(5) -0.1151(2) 0.124(2) Uani 1 d . . H23A H 0.0288(2) 0.4808(5) -0.1355(2) 0.186 Uiso 1 calc R . H23B H -0.0167(2) 0.4772(5) -0.1016(2) 0.186 Uiso 1 calc R . H23C H -0.0072(2) 0.3564(5) -0.1563(2) 0.186 Uiso 1 calc R . C24 C 0.1009(2) -0.0278(5) 0.3354(3) 0.126(2) Uani 1 d . . H24A H 0.1110(2) -0.0055(5) 0.3926(3) 0.189 Uiso 1 calc R . H24B H 0.0734(2) -0.0880(5) 0.3246(3) 0.189 Uiso 1 calc R . H24C H 0.0924(2) 0.0551(5) 0.3040(3) 0.189 Uiso 1 calc R . C25 C 0.1685(2) -0.1810(6) 0.3777(3) 0.137(2) Uani 1 d . . H25A H 0.1702(2) -0.1391(6) 0.4296(3) 0.205 Uiso 1 calc R . H25B H 0.2006(2) -0.1906(6) 0.3716(3) 0.205 Uiso 1 calc R . H25C H 0.1537(2) -0.2701(6) 0.3752(3) 0.205 Uiso 1 calc R . C26 C 0.13162(15) -0.3201(5) 0.1345(4) 0.1029(15) Uani 1 d . . H26 H 0.13494(15) -0.4130(5) 0.1240(4) 0.124 Uiso 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 0.051(2) 0.055(4) 0.067(2) 0.001(2) 0.024(2) 0.001(2) N1 0.104(2) 0.074(3) 0.093(2) 0.020(2) 0.033(2) 0.006(2) C1 0.060(2) 0.062(3) 0.062(2) -0.007(2) 0.019(2) -0.002(2) C2 0.062(2) 0.055(2) 0.060(2) 0.003(2) 0.0139(15) 0.001(2) C3 0.056(2) 0.055(3) 0.067(2) -0.001(2) 0.017(2) -0.003(2) C4 0.049(2) 0.064(4) 0.074(2) -0.005(2) 0.016(2) 0.000(2) C5 0.061(2) 0.050(2) 0.056(2) 0.002(2) 0.0203(15) 0.007(2) C6 0.055(2) 0.066(3) 0.079(2) 0.003(2) 0.012(2) 0.001(2) C7 0.069(2) 0.059(3) 0.064(2) 0.002(2) 0.022(2) 0.008(2) C8 0.090(3) 0.062(3) 0.055(2) 0.002(2) 0.016(2) -0.005(2) C9 0.053(2) 0.101(3) 0.087(2) 0.013(2) 0.008(2) 0.006(2) C10 0.103(3) 0.062(3) 0.061(2) -0.005(2) 0.029(2) 0.007(2) C11 0.069(2) 0.065(3) 0.063(2) 0.000(2) 0.011(2) -0.001(2) C12 0.059(2) 0.089(3) 0.094(2) -0.017(2) 0.017(2) 0.007(2) C13 0.068(2) 0.078(3) 0.083(2) 0.003(2) 0.028(2) -0.013(2) C14 0.078(2) 0.075(3) 0.070(2) 0.013(2) 0.022(2) -0.001(2) C15 0.063(2) 0.054(4) 0.093(3) 0.002(2) 0.019(2) 0.000(2) C16 0.071(3) 0.095(4) 0.116(4) -0.049(4) 0.005(2) 0.001(3) C17 0.076(2) 0.095(3) 0.078(2) 0.013(2) 0.012(2) 0.011(2) C18 0.059(2) 0.099(4) 0.118(3) 0.015(3) 0.021(2) -0.012(2) C19 0.062(2) 0.083(4) 0.080(2) -0.023(2) 0.002(2) -0.001(2) C20 0.089(3) 0.099(3) 0.105(3) -0.011(3) 0.029(2) 0.032(2) C21 0.131(3) 0.086(3) 0.069(2) -0.019(2) 0.015(2) -0.019(3) C22 0.077(3) 0.063(4) 0.134(4) 0.006(3) 0.018(3) 0.003(2) C23 0.102(3) 0.158(5) 0.101(3) 0.049(3) 0.009(2) 0.023(3) C24 0.150(4) 0.123(5) 0.127(4) 0.015(3) 0.076(3) 0.020(4) C25 0.167(5) 0.126(5) 0.106(3) 0.035(3) 0.018(3) 0.012(4) C26 0.080(3) 0.067(4) 0.151(4) -0.029(4) 0.012(3) 0.004(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 C4 1.555(6) . B1 C3 1.573(5) . B1 C5 1.593(5) . N1 C15 1.415(5) . N1 C24 1.440(5) . N1 C25 1.444(5) . C1 C14 1.386(4) . C1 C3 1.403(4) . C1 C13 1.513(4) . C2 C11 1.394(4) . C2 C5 1.413(4) . C2 C12 1.506(4) . C3 C6 1.415(4) . C4 C15 1.396(5) . C4 C19 1.397(5) . C5 C7 1.402(4) . C6 C9 1.376(5) . C6 C18 1.499(4) . C7 C10 1.388(4) . C7 C20 1.507(5) . C8 C10 1.368(5) . C8 C11 1.372(5) . C8 C21 1.515(5) . C9 C17 1.374(5) . C14 C17 1.379(5) . C15 C22 1.400(5) . C16 C26 1.357(6) . C16 C19 1.384(5) . C17 C23 1.511(5) . C22 C26 1.362(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 C4 B1 C3 117.4(3) . . C4 B1 C5 123.7(3) . . C3 B1 C5 118.7(3) . . C15 N1 C24 118.7(3) . . C15 N1 C25 119.3(4) . . C24 N1 C25 112.2(4) . . C14 C1 C3 120.6(3) . . C14 C1 C13 118.3(3) . . C3 C1 C13 121.0(3) . . C11 C2 C5 119.9(3) . . C11 C2 C12 117.3(3) . . C5 C2 C12 122.9(3) . . C1 C3 C6 116.9(3) . . C1 C3 B1 121.4(3) . . C6 C3 B1 121.6(3) . . C15 C4 C19 116.7(4) . . C15 C4 B1 127.0(3) . . C19 C4 B1 115.9(4) . . C7 C5 C2 117.2(3) . . C7 C5 B1 121.5(3) . . C2 C5 B1 121.2(3) . . C9 C6 C3 120.1(3) . . C9 C6 C18 117.7(3) . . C3 C6 C18 122.2(3) . . C10 C7 C5 120.3(3) . . C10 C7 C20 117.2(3) . . C5 C7 C20 122.5(3) . . C10 C8 C11 117.2(3) . . C10 C8 C21 121.9(4) . . C11 C8 C21 120.8(4) . . C17 C9 C6 123.2(3) . . C8 C10 C7 122.7(3) . . C8 C11 C2 122.6(3) . . C17 C14 C1 122.4(3) . . C4 C15 C22 119.9(4) . . C4 C15 N1 120.5(4) . . C22 C15 N1 119.6(4) . . C26 C16 C19 119.2(4) . . C9 C17 C14 116.8(3) . . C9 C17 C23 121.4(4) . . C14 C17 C23 121.8(4) . . C16 C19 C4 122.6(4) . . C26 C22 C15 121.1(5) . . C16 C26 C22 120.4(5) . . _refine_diff_density_max 0.254 _refine_diff_density_min -0.209 _refine_diff_density_rms 0.044