# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2006 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name "Donal O'Shea" _publ_contact_author_address ; Department of Chemistry University College Dublin Dublin 4 REPUBLIC OF IRELAND ; _publ_contact_author_email DONAL.F.OSHEA@UCD.IE _publ_section_title ; Impact of a Conformationally Restricted Receptor on the BF2 Chelated Azadipyrromethene Fluorosensing Platform ; loop_ _publ_author_name O.Donal 'John Killoran' ## -END- ## # Attachment 'X-ray structure 1b.cif' data_osh30 _database_code_depnum_ccdc_archive 'CCDC 285001' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; BF2 chelated (3,5-Diphenyl-1H-pyrrol-2-yl)-(3-(4- dimethylamino-2,6 -dimethylphenyl)-5-phenylpyrrol-2-ylidene)-amine ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H31 B N4 F2' _chemical_formula_weight 568.46 _chemical_absolute_configuration unk 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0000 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 42.555(7) _cell_length_b 5.3195(9) _cell_length_c 12.780(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.405(4) _cell_angle_gamma 90.00 _cell_volume 2814.3(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1305 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 22.19 _exptl_crystal_description lath _exptl_crystal_colour black _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1192 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5272 _exptl_absorpt_correction_T_max 0.9991 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 8079 _diffrn_reflns_av_R_equivalents 0.0702 _diffrn_reflns_av_sigmaI/netI 0.0769 _diffrn_reflns_limit_h_min -48 _diffrn_reflns_limit_h_max 48 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 24.14 _reflns_number_total 2219 _reflns_number_gt 1710 _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^)+(0.0568P)^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_abs_structure_details ? _refine_ls_number_reflns 2219 _refine_ls_number_parameters 392 _refine_ls_number_restraints 124 _refine_ls_R_factor_all 0.0774 _refine_ls_R_factor_gt 0.0478 _refine_ls_wR_factor_ref 0.1081 _refine_ls_wR_factor_gt 0.0974 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.029 _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 B B 0.37849(14) -0.0312(12) 0.3164(5) 0.0205(13) Uani 1 1 d U . . F1 F 0.39011(6) -0.2728(6) 0.3142(2) 0.0227(7) Uani 1 1 d U . . F2 F 0.36250(6) 0.0418(5) 0.2123(2) 0.0223(7) Uani 1 1 d U . . N1 N 0.38948(9) 0.2426(8) 0.5248(3) 0.0193(10) Uani 1 1 d U . . N2 N 0.40694(9) 0.1528(8) 0.3620(3) 0.0184(10) Uani 1 1 d U . . N3 N 0.35481(8) -0.0116(8) 0.3915(3) 0.0177(10) Uani 1 1 d U . . N4 N 0.34532(10) 0.5826(9) 0.9445(3) 0.0285(12) Uani 1 1 d U . . C1 C 0.41131(11) 0.2611(10) 0.4653(4) 0.0175(11) Uani 1 1 d U . . C2 C 0.43944(11) 0.4103(10) 0.4879(4) 0.0191(12) Uani 1 1 d U . . C3 C 0.45252(11) 0.3930(11) 0.3984(4) 0.0212(12) Uani 1 1 d U . . H3 H 0.4713 0.4709 0.3899 0.025 Uiso 1 1 calc R . . C4 C 0.43235(11) 0.2369(10) 0.3230(4) 0.0181(11) Uani 1 1 d U . . C5 C 0.45175(10) 0.5636(10) 0.5847(4) 0.0177(12) Uani 1 1 d U . . C6 C 0.44729(11) 0.4963(11) 0.6866(4) 0.0218(13) Uani 1 1 d U . . H6 H 0.4351 0.3555 0.6944 0.026 Uiso 1 1 calc R . . C7 C 0.46120(11) 0.6406(11) 0.7754(4) 0.0215(12) Uani 1 1 d U . . H7 H 0.4581 0.5961 0.8427 0.026 Uiso 1 1 calc R . . C8 C 0.47955(12) 0.8489(11) 0.7661(4) 0.0244(13) Uani 1 1 d U . . H8 H 0.4897 0.9389 0.8269 0.029 Uiso 1 1 calc R . . C9 C 0.48282(11) 0.9235(11) 0.6650(4) 0.0254(13) Uani 1 1 d U . . H9 H 0.4943 1.0686 0.6574 0.031 Uiso 1 1 calc R . . C10 C 0.46907(11) 0.7820(10) 0.5763(4) 0.0216(13) Uani 1 1 d U . . H10 H 0.4714 0.8332 0.5089 0.026 Uiso 1 1 calc R . . C11 C 0.43787(11) 0.1866(10) 0.2142(4) 0.0178(12) Uani 1 1 d U . . C12 C 0.45658(11) 0.3617(11) 0.1741(4) 0.0215(13) Uani 1 1 d U . . H12 H 0.4652 0.4991 0.2160 0.026 Uiso 1 1 calc R . . C13 C 0.46251(12) 0.3322(11) 0.0713(4) 0.0243(13) Uani 1 1 d U . . H13 H 0.4752 0.4489 0.0457 0.029 Uiso 1 1 calc R . . C14 C 0.44962(12) 0.1318(11) 0.0086(4) 0.0248(13) Uani 1 1 d U . . H14 H 0.4530 0.1151 -0.0604 0.030 Uiso 1 1 calc R . . C15 C 0.43150(11) -0.0469(11) 0.0484(4) 0.0240(13) Uani 1 1 d U . . H15 H 0.4230 -0.1842 0.0061 0.029 Uiso 1 1 calc R . . C16 C 0.42596(11) -0.0210(11) 0.1515(4) 0.0202(12) Uani 1 1 d U . . H16 H 0.4143 -0.1432 0.1782 0.024 Uiso 1 1 calc R . . C17 C 0.36271(11) 0.1169(10) 0.4908(4) 0.0168(12) Uani 1 1 d U . . C18 C 0.33538(11) 0.1149(10) 0.5381(4) 0.0197(12) Uani 1 1 d U . . C19 C 0.31089(11) 0.0014(11) 0.4638(4) 0.0224(13) Uani 1 1 d U . . H19 H 0.2897 -0.0175 0.4699 0.027 Uiso 1 1 calc R . . C20 C 0.32343(12) -0.0815(10) 0.3767(4) 0.0197(12) Uani 1 1 d U . . C21 C 0.33598(11) 0.2213(10) 0.6458(4) 0.0196(12) Uani 1 1 d U . . C22 C 0.36039(11) 0.1441(10) 0.7360(4) 0.0209(12) Uani 1 1 d U . . C23 C 0.36215(11) 0.2634(11) 0.8341(4) 0.0221(13) Uani 1 1 d U . . H23 H 0.3779 0.2116 0.8934 0.027 Uiso 1 1 calc R . . C24 C 0.34136(11) 0.4569(11) 0.8474(4) 0.0200(12) Uani 1 1 d U . . C25 C 0.31619(11) 0.5185(10) 0.7582(4) 0.0218(13) Uani 1 1 d U . . H25 H 0.3013 0.6415 0.7656 0.026 Uiso 1 1 calc R . . C26 C 0.31310(11) 0.3993(10) 0.6595(4) 0.0195(12) Uani 1 1 d U . . C27 C 0.30491(11) -0.2346(10) 0.2868(4) 0.0197(12) Uani 1 1 d U . . C28 C 0.27208(11) -0.1817(10) 0.2473(4) 0.0226(13) Uani 1 1 d U . . H28 H 0.2628 -0.0460 0.2749 0.027 Uiso 1 1 calc R . . C29 C 0.25319(12) -0.3291(11) 0.1676(4) 0.0286(14) Uani 1 1 d U . . H29 H 0.2315 -0.2908 0.1406 0.034 Uiso 1 1 calc R . . C30 C 0.26709(12) -0.5352(11) 0.1285(4) 0.0284(14) Uani 1 1 d U . . H30 H 0.2546 -0.6363 0.0755 0.034 Uiso 1 1 calc R . . C31 C 0.29935(11) -0.5903(11) 0.1679(4) 0.0250(13) Uani 1 1 d U . . H31 H 0.3084 -0.7282 0.1411 0.030 Uiso 1 1 calc R . . C32 C 0.31828(12) -0.4430(10) 0.2465(4) 0.0237(13) Uani 1 1 d U . . H32 H 0.3400 -0.4823 0.2728 0.028 Uiso 1 1 calc R . . C33 C 0.38333(12) -0.0692(10) 0.7304(4) 0.0230(13) Uani 1 1 d U . . H33A H 0.3727 -0.1911 0.6788 0.035 Uiso 1 1 calc R . . H33B H 0.3899 -0.1471 0.7998 0.035 Uiso 1 1 calc R . . H33C H 0.4020 -0.0052 0.7091 0.035 Uiso 1 1 calc R . . C34 C 0.36712(11) 0.4812(12) 1.0394(4) 0.0288(14) Uani 1 1 d U . . H34A H 0.3605 0.3136 1.0522 0.043 Uiso 1 1 calc R . . H34B H 0.3666 0.5852 1.1003 0.043 Uiso 1 1 calc R . . H34C H 0.3887 0.4776 1.0284 0.043 Uiso 1 1 calc R . . C35 C 0.32196(12) 0.7688(11) 0.9576(4) 0.0291(14) Uani 1 1 d U . . H35A H 0.3203 0.8953 0.9030 0.044 Uiso 1 1 calc R . . H35B H 0.3287 0.8452 1.0272 0.044 Uiso 1 1 calc R . . H35C H 0.3013 0.6901 0.9512 0.044 Uiso 1 1 calc R . . C36 C 0.28438(11) 0.4687(12) 0.5690(4) 0.0270(13) Uani 1 1 d U . . H36A H 0.2681 0.3411 0.5623 0.041 Uiso 1 1 calc R . . H36B H 0.2912 0.4819 0.5028 0.041 Uiso 1 1 calc R . . H36C H 0.2757 0.6270 0.5849 0.041 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 B 0.021(3) 0.024(4) 0.014(3) 0.005(3) -0.003(2) 0.004(3) F1 0.0264(16) 0.0256(18) 0.0143(15) 0.0014(14) 0.0007(12) 0.0008(14) F2 0.0264(15) 0.0313(19) 0.0063(14) 0.0016(13) -0.0019(12) -0.0007(14) N1 0.017(2) 0.025(3) 0.014(2) 0.002(2) 0.0000(19) 0.002(2) N2 0.019(2) 0.026(3) 0.008(2) -0.002(2) -0.0023(18) -0.0011(19) N3 0.016(2) 0.027(3) 0.009(2) 0.001(2) -0.0005(17) 0.001(2) N4 0.035(3) 0.036(3) 0.010(2) -0.001(2) -0.004(2) 0.012(2) C1 0.018(3) 0.020(3) 0.013(3) 0.002(2) 0.001(2) 0.004(2) C2 0.016(3) 0.026(3) 0.013(3) 0.004(2) -0.002(2) 0.002(2) C3 0.018(3) 0.031(3) 0.013(3) -0.003(3) 0.001(2) -0.003(2) C4 0.015(3) 0.023(3) 0.014(3) 0.002(2) -0.002(2) 0.009(2) C5 0.013(3) 0.021(3) 0.017(3) 0.000(2) 0.000(2) 0.001(2) C6 0.024(3) 0.024(3) 0.017(3) 0.001(3) 0.003(2) 0.000(3) C7 0.020(3) 0.036(3) 0.007(3) -0.002(3) 0.001(2) 0.001(3) C8 0.022(3) 0.033(3) 0.014(3) -0.008(3) -0.004(2) 0.002(3) C9 0.021(3) 0.028(3) 0.024(3) -0.006(3) 0.000(2) -0.005(3) C10 0.020(3) 0.028(3) 0.016(3) 0.000(3) 0.002(2) -0.001(2) C11 0.016(3) 0.024(3) 0.010(3) 0.002(2) -0.002(2) 0.002(2) C12 0.022(3) 0.030(3) 0.010(3) -0.003(2) -0.002(2) 0.001(2) C13 0.026(3) 0.034(3) 0.012(3) 0.004(3) 0.002(2) 0.001(3) C14 0.029(3) 0.034(4) 0.011(3) -0.002(3) 0.005(2) 0.007(3) C15 0.027(3) 0.029(3) 0.013(3) -0.003(3) -0.001(2) 0.003(3) C16 0.019(3) 0.025(3) 0.015(3) 0.003(2) 0.000(2) 0.003(2) C17 0.011(2) 0.021(3) 0.015(3) 0.003(2) -0.004(2) -0.001(2) C18 0.021(3) 0.021(3) 0.014(3) -0.002(2) 0.000(2) 0.001(2) C19 0.017(3) 0.031(4) 0.018(3) 0.001(3) 0.001(2) -0.005(3) C20 0.024(3) 0.025(3) 0.008(3) 0.005(2) 0.001(2) 0.001(2) C21 0.018(3) 0.028(3) 0.011(3) -0.002(2) 0.001(2) -0.002(2) C22 0.023(3) 0.026(3) 0.014(3) 0.000(3) 0.005(2) -0.004(2) C23 0.018(3) 0.034(3) 0.010(3) 0.004(3) -0.006(2) 0.000(3) C24 0.015(3) 0.033(3) 0.012(3) 0.001(2) 0.001(2) 0.000(2) C25 0.021(3) 0.027(3) 0.016(3) -0.003(3) 0.001(2) -0.001(2) C26 0.014(3) 0.033(4) 0.010(3) 0.001(3) -0.001(2) -0.003(2) C27 0.021(3) 0.023(3) 0.014(3) 0.002(2) 0.002(2) -0.006(3) C28 0.021(3) 0.026(3) 0.020(3) -0.002(2) 0.004(2) 0.000(2) C29 0.023(3) 0.040(4) 0.019(3) -0.001(3) -0.004(2) -0.006(3) C30 0.030(3) 0.034(4) 0.020(3) -0.007(3) 0.004(2) -0.011(3) C31 0.025(3) 0.029(4) 0.020(3) -0.011(3) 0.004(2) -0.007(3) C32 0.024(3) 0.024(3) 0.022(3) 0.001(3) 0.005(2) 0.003(3) C33 0.029(3) 0.029(3) 0.010(3) 0.002(3) 0.001(2) 0.002(3) C34 0.034(3) 0.037(4) 0.013(3) -0.001(3) 0.000(2) -0.001(3) C35 0.038(3) 0.032(4) 0.016(3) -0.004(3) 0.002(3) 0.004(3) C36 0.028(3) 0.035(4) 0.016(3) -0.001(3) 0.000(2) 0.003(3) _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 B F1 1.380(7) . ? B F2 1.402(6) . ? B N3 1.547(7) . ? B N2 1.561(7) . ? N1 C17 1.305(6) . ? N1 C1 1.334(6) . ? N2 C4 1.367(6) . ? N2 C1 1.413(6) . ? N3 C20 1.356(6) . ? N3 C17 1.412(6) . ? N4 C24 1.385(6) . ? N4 C35 1.440(6) . ? N4 C34 1.449(6) . ? C1 C2 1.409(7) . ? C2 C3 1.385(7) . ? C2 C5 1.473(7) . ? C3 C4 1.404(7) . ? C3 H3 0.9300 . ? C4 C11 1.487(7) . ? C5 C10 1.393(7) . ? C5 C6 1.406(6) . ? C6 C7 1.384(7) . ? C6 H6 0.9300 . ? C7 C8 1.377(8) . ? C7 H7 0.9300 . ? C8 C9 1.389(7) . ? C8 H8 0.9300 . ? C9 C10 1.373(7) . ? C9 H9 0.9300 . ? C10 H10 0.9300 . ? C11 C16 1.389(7) . ? C11 C12 1.398(7) . ? C12 C13 1.402(7) . ? C12 H12 0.9300 . ? C13 C14 1.370(7) . ? C13 H13 0.9300 . ? C14 C15 1.392(7) . ? C14 H14 0.9300 . ? C15 C16 1.399(7) . ? C15 H15 0.9300 . ? C16 H16 0.9300 . ? C17 C18 1.430(6) . ? C18 C19 1.376(7) . ? C18 C21 1.484(7) . ? C19 C20 1.412(7) . ? C19 H19 0.9300 . ? C20 C27 1.478(7) . ? C21 C26 1.398(7) . ? C21 C22 1.422(6) . ? C22 C23 1.391(7) . ? C22 C33 1.509(7) . ? C23 C24 1.393(7) . ? C23 H23 0.9300 . ? C24 C25 1.410(6) . ? C25 C26 1.391(7) . ? C25 H25 0.9300 . ? C26 C36 1.520(6) . ? C27 C32 1.398(7) . ? C27 C28 1.400(6) . ? C28 C29 1.385(7) . ? C28 H28 0.9300 . ? C29 C30 1.393(8) . ? C29 H29 0.9300 . ? C30 C31 1.379(7) . ? C30 H30 0.9300 . ? C31 C32 1.377(7) . ? C31 H31 0.9300 . ? C32 H32 0.9300 . ? C33 H33A 0.9600 . ? C33 H33B 0.9600 . ? C33 H33C 0.9600 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 H35A 0.9600 . ? C35 H35B 0.9600 . ? C35 H35C 0.9600 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 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 F1 B F2 109.6(5) . . ? F1 B N3 111.3(4) . . ? F2 B N3 109.1(4) . . ? F1 B N2 109.9(4) . . ? F2 B N2 110.1(4) . . ? N3 B N2 106.7(4) . . ? C17 N1 C1 121.2(4) . . ? C4 N2 C1 105.3(4) . . ? C4 N2 B 132.8(4) . . ? C1 N2 B 121.8(4) . . ? C20 N3 C17 106.2(4) . . ? C20 N3 B 131.1(4) . . ? C17 N3 B 122.4(4) . . ? C24 N4 C35 119.5(4) . . ? C24 N4 C34 119.4(4) . . ? C35 N4 C34 119.0(4) . . ? N1 C1 C2 126.6(5) . . ? N1 C1 N2 123.0(4) . . ? C2 C1 N2 110.0(4) . . ? C3 C2 C1 106.2(4) . . ? C3 C2 C5 126.7(4) . . ? C1 C2 C5 127.1(4) . . ? C2 C3 C4 107.9(4) . . ? C2 C3 H3 126.1 . . ? C4 C3 H3 126.1 . . ? N2 C4 C3 110.7(4) . . ? N2 C4 C11 126.3(4) . . ? C3 C4 C11 123.0(4) . . ? C10 C5 C6 118.1(5) . . ? C10 C5 C2 119.2(5) . . ? C6 C5 C2 122.7(5) . . ? C7 C6 C5 119.6(5) . . ? C7 C6 H6 120.2 . . ? C5 C6 H6 120.2 . . ? C8 C7 C6 121.2(5) . . ? C8 C7 H7 119.4 . . ? C6 C7 H7 119.4 . . ? C7 C8 C9 119.5(5) . . ? C7 C8 H8 120.3 . . ? C9 C8 H8 120.3 . . ? C10 C9 C8 119.7(5) . . ? C10 C9 H9 120.2 . . ? C8 C9 H9 120.2 . . ? C9 C10 C5 121.7(5) . . ? C9 C10 H10 119.1 . . ? C5 C10 H10 119.1 . . ? C16 C11 C12 118.7(4) . . ? C16 C11 C4 124.5(5) . . ? C12 C11 C4 116.8(5) . . ? C11 C12 C13 120.7(5) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C14 C13 C12 120.0(5) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 119.9(5) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C16 120.4(5) . . ? C14 C15 H15 119.8 . . ? C16 C15 H15 119.8 . . ? C11 C16 C15 120.2(5) . . ? C11 C16 H16 119.9 . . ? C15 C16 H16 119.9 . . ? N1 C17 N3 123.7(4) . . ? N1 C17 C18 126.5(5) . . ? N3 C17 C18 109.2(4) . . ? C19 C18 C17 105.8(4) . . ? C19 C18 C21 130.9(4) . . ? C17 C18 C21 123.3(4) . . ? C18 C19 C20 108.5(4) . . ? C18 C19 H19 125.8 . . ? C20 C19 H19 125.8 . . ? N3 C20 C19 110.2(4) . . ? N3 C20 C27 126.1(4) . . ? C19 C20 C27 123.6(4) . . ? C26 C21 C22 119.6(4) . . ? C26 C21 C18 120.8(4) . . ? C22 C21 C18 119.6(5) . . ? C23 C22 C21 118.4(5) . . ? C23 C22 C33 119.0(4) . . ? C21 C22 C33 122.5(4) . . ? C22 C23 C24 123.0(4) . . ? C22 C23 H23 118.5 . . ? C24 C23 H23 118.5 . . ? N4 C24 C23 121.1(4) . . ? N4 C24 C25 121.6(5) . . ? C23 C24 C25 117.3(5) . . ? C26 C25 C24 121.4(5) . . ? C26 C25 H25 119.3 . . ? C24 C25 H25 119.3 . . ? C25 C26 C21 120.0(4) . . ? C25 C26 C36 118.0(5) . . ? C21 C26 C36 122.0(4) . . ? C32 C27 C28 119.0(5) . . ? C32 C27 C20 122.3(4) . . ? C28 C27 C20 118.5(5) . . ? C29 C28 C27 120.8(5) . . ? C29 C28 H28 119.6 . . ? C27 C28 H28 119.6 . . ? C28 C29 C30 119.2(5) . . ? C28 C29 H29 120.4 . . ? C30 C29 H29 120.4 . . ? C31 C30 C29 120.4(5) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C32 C31 C30 120.7(5) . . ? C32 C31 H31 119.7 . . ? C30 C31 H31 119.7 . . ? C31 C32 C27 120.0(5) . . ? C31 C32 H32 120.0 . . ? C27 C32 H32 120.0 . . ? C22 C33 H33A 109.5 . . ? C22 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C22 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N4 C34 H34A 109.5 . . ? N4 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N4 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N4 C35 H35A 109.5 . . ? N4 C35 H35B 109.5 . . ? H35A C35 H35B 109.5 . . ? N4 C35 H35C 109.5 . . ? H35A C35 H35C 109.5 . . ? H35B C35 H35C 109.5 . . ? C26 C36 H36A 109.5 . . ? C26 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C26 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 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 F1 B N2 C4 68.5(7) . . . . ? F2 B N2 C4 -52.4(7) . . . . ? N3 B N2 C4 -170.6(5) . . . . ? F1 B N2 C1 -108.2(5) . . . . ? F2 B N2 C1 130.9(5) . . . . ? N3 B N2 C1 12.6(6) . . . . ? F1 B N3 C20 -77.6(6) . . . . ? F2 B N3 C20 43.5(7) . . . . ? N2 B N3 C20 162.5(5) . . . . ? F1 B N3 C17 109.5(5) . . . . ? F2 B N3 C17 -129.4(5) . . . . ? N2 B N3 C17 -10.4(6) . . . . ? C17 N1 C1 C2 173.3(5) . . . . ? C17 N1 C1 N2 1.3(8) . . . . ? C4 N2 C1 N1 173.2(5) . . . . ? B N2 C1 N1 -9.3(7) . . . . ? C4 N2 C1 C2 0.0(5) . . . . ? B N2 C1 C2 177.5(4) . . . . ? N1 C1 C2 C3 -173.1(5) . . . . ? N2 C1 C2 C3 -0.3(6) . . . . ? N1 C1 C2 C5 4.3(8) . . . . ? N2 C1 C2 C5 177.2(4) . . . . ? C1 C2 C3 C4 0.4(6) . . . . ? C5 C2 C3 C4 -177.0(5) . . . . ? C1 N2 C4 C3 0.3(5) . . . . ? B N2 C4 C3 -176.8(5) . . . . ? C1 N2 C4 C11 -176.6(5) . . . . ? B N2 C4 C11 6.3(8) . . . . ? C2 C3 C4 N2 -0.5(6) . . . . ? C2 C3 C4 C11 176.5(5) . . . . ? C3 C2 C5 C10 27.6(8) . . . . ? C1 C2 C5 C10 -149.4(5) . . . . ? C3 C2 C5 C6 -151.2(5) . . . . ? C1 C2 C5 C6 31.9(7) . . . . ? C10 C5 C6 C7 -2.7(7) . . . . ? C2 C5 C6 C7 176.0(5) . . . . ? C5 C6 C7 C8 -0.4(7) . . . . ? C6 C7 C8 C9 3.4(7) . . . . ? C7 C8 C9 C10 -3.2(7) . . . . ? C8 C9 C10 C5 0.0(7) . . . . ? C6 C5 C10 C9 2.9(7) . . . . ? C2 C5 C10 C9 -175.9(4) . . . . ? N2 C4 C11 C16 -25.6(8) . . . . ? C3 C4 C11 C16 158.0(5) . . . . ? N2 C4 C11 C12 154.9(5) . . . . ? C3 C4 C11 C12 -21.6(7) . . . . ? C16 C11 C12 C13 1.7(7) . . . . ? C4 C11 C12 C13 -178.7(4) . . . . ? C11 C12 C13 C14 0.7(7) . . . . ? C12 C13 C14 C15 -2.0(7) . . . . ? C13 C14 C15 C16 0.9(7) . . . . ? C12 C11 C16 C15 -2.8(7) . . . . ? C4 C11 C16 C15 177.7(5) . . . . ? C14 C15 C16 C11 1.5(7) . . . . ? C1 N1 C17 N3 1.2(7) . . . . ? C1 N1 C17 C18 -169.5(5) . . . . ? C20 N3 C17 N1 -170.0(5) . . . . ? B N3 C17 N1 4.4(7) . . . . ? C20 N3 C17 C18 2.2(5) . . . . ? B N3 C17 C18 176.6(4) . . . . ? N1 C17 C18 C19 167.8(5) . . . . ? N3 C17 C18 C19 -4.0(6) . . . . ? N1 C17 C18 C21 -11.7(8) . . . . ? N3 C17 C18 C21 176.4(5) . . . . ? C17 C18 C19 C20 4.3(6) . . . . ? C21 C18 C19 C20 -176.2(5) . . . . ? C17 N3 C20 C19 0.6(6) . . . . ? B N3 C20 C19 -173.2(5) . . . . ? C17 N3 C20 C27 -176.1(5) . . . . ? B N3 C20 C27 10.2(9) . . . . ? C18 C19 C20 N3 -3.2(6) . . . . ? C18 C19 C20 C27 173.6(5) . . . . ? C19 C18 C21 C26 -53.1(8) . . . . ? C17 C18 C21 C26 126.3(5) . . . . ? C19 C18 C21 C22 127.9(6) . . . . ? C17 C18 C21 C22 -52.8(7) . . . . ? C26 C21 C22 C23 -4.8(7) . . . . ? C18 C21 C22 C23 174.3(5) . . . . ? C26 C21 C22 C33 172.3(4) . . . . ? C18 C21 C22 C33 -8.6(7) . . . . ? C21 C22 C23 C24 -0.9(7) . . . . ? C33 C22 C23 C24 -178.1(5) . . . . ? C35 N4 C24 C23 -175.4(5) . . . . ? C34 N4 C24 C23 -12.2(7) . . . . ? C35 N4 C24 C25 4.4(7) . . . . ? C34 N4 C24 C25 167.6(5) . . . . ? C22 C23 C24 N4 -175.5(5) . . . . ? C22 C23 C24 C25 4.7(7) . . . . ? N4 C24 C25 C26 177.2(5) . . . . ? C23 C24 C25 C26 -3.0(7) . . . . ? C24 C25 C26 C21 -2.6(7) . . . . ? C24 C25 C26 C36 177.3(5) . . . . ? C22 C21 C26 C25 6.5(7) . . . . ? C18 C21 C26 C25 -172.6(5) . . . . ? C22 C21 C26 C36 -173.4(5) . . . . ? C18 C21 C26 C36 7.6(7) . . . . ? N3 C20 C27 C32 40.7(8) . . . . ? C19 C20 C27 C32 -135.6(5) . . . . ? N3 C20 C27 C28 -145.1(5) . . . . ? C19 C20 C27 C28 38.7(7) . . . . ? C32 C27 C28 C29 -1.7(7) . . . . ? C20 C27 C28 C29 -176.1(5) . . . . ? C27 C28 C29 C30 1.4(8) . . . . ? C28 C29 C30 C31 -0.6(8) . . . . ? C29 C30 C31 C32 0.1(8) . . . . ? C30 C31 C32 C27 -0.4(8) . . . . ? C28 C27 C32 C31 1.1(7) . . . . ? C20 C27 C32 C31 175.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.881 _diffrn_reflns_theta_full 24.14 _diffrn_measured_fraction_theta_full 0.881 _refine_diff_density_max 0.275 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.056 ## -END- ## data_osh38 _database_code_depnum_ccdc_archive 'CCDC 285002' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; BF2 chelated (3,5-Diphenyl-1H-pyrrol-2-yl)-(3-(4- dimethylaminophenyl) -5-phenylpyrrol-2-ylidene)-amine ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H27 B N4 F2' _chemical_formula_weight 540.41 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.755(3) _cell_length_b 10.824(3) _cell_length_c 12.163(4) _cell_angle_alpha 91.726(6) _cell_angle_beta 113.148(5) _cell_angle_gamma 96.565(6) _cell_volume 1288.9(7) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 1344 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 23.97 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6896 _exptl_absorpt_correction_T_max 0.9963 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(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 8293 _diffrn_reflns_av_R_equivalents 0.0477 _diffrn_reflns_av_sigmaI/netI 0.0806 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 24.00 _reflns_number_total 4000 _reflns_number_gt 2719 _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^)+(0.0259P)^2^+8.1530P] 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 4000 _refine_ls_number_parameters 372 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1241 _refine_ls_R_factor_gt 0.0865 _refine_ls_wR_factor_ref 0.2235 _refine_ls_wR_factor_gt 0.2086 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.178 _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 B B 0.2674(7) 0.2442(6) 0.1786(6) 0.0175(15) Uani 1 1 d . . . F1 F 0.1522(3) 0.2429(3) 0.2016(3) 0.0242(9) Uani 1 1 d . . . F2 F 0.3092(3) 0.3614(3) 0.1528(3) 0.0248(9) Uani 1 1 d . . . N1 N 0.4297(5) 0.0375(5) 0.1762(4) 0.0180(12) Uani 1 1 d . . . N2 N 0.2389(5) 0.1458(4) 0.0712(4) 0.0176(11) Uani 1 1 d . . . N3 N 0.3879(5) 0.2022(4) 0.2874(4) 0.0175(11) Uani 1 1 d . . . N4 N 0.9606(5) -0.2332(5) 0.4746(5) 0.0273(13) Uani 1 1 d . . . C1 C 0.3171(6) 0.0494(6) 0.0802(5) 0.0186(14) Uani 1 1 d . . . C2 C 0.2523(6) -0.0375(6) -0.0208(5) 0.0190(14) Uani 1 1 d . . . C3 C 0.1341(6) 0.0081(6) -0.0900(5) 0.0193(14) Uani 1 1 d . . . H3 H 0.0677 -0.0305 -0.1642 0.023 Uiso 1 1 calc R . . C4 C 0.1272(6) 0.1197(5) -0.0342(5) 0.0159(13) Uani 1 1 d . . . C5 C 0.2953(6) -0.1563(6) -0.0412(5) 0.0196(14) Uani 1 1 d . . . C6 C 0.1967(7) -0.2569(6) -0.1043(6) 0.0253(15) Uani 1 1 d . . . H6 H 0.1027 -0.2475 -0.1340 0.030 Uiso 1 1 calc R . . C7 C 0.2352(7) -0.3697(6) -0.1236(6) 0.0285(16) Uani 1 1 d . . . H7 H 0.1671 -0.4374 -0.1671 0.034 Uiso 1 1 calc R . . C8 C 0.3702(7) -0.3860(6) -0.0811(6) 0.0302(17) Uani 1 1 d . . . H8 H 0.3953 -0.4644 -0.0953 0.036 Uiso 1 1 calc R . . C9 C 0.4695(7) -0.2878(6) -0.0174(6) 0.0295(16) Uani 1 1 d . . . H9 H 0.5632 -0.2987 0.0124 0.035 Uiso 1 1 calc R . . C10 C 0.4323(7) -0.1731(6) 0.0031(6) 0.0241(15) Uani 1 1 d . . . H10 H 0.5007 -0.1060 0.0474 0.029 Uiso 1 1 calc R . . C11 C 0.0203(6) 0.1992(6) -0.0838(5) 0.0185(14) Uani 1 1 d . . . C12 C 0.0420(7) 0.3291(6) -0.0731(6) 0.0238(15) Uani 1 1 d . . . H12 H 0.1314 0.3721 -0.0299 0.029 Uiso 1 1 calc R . . C13 C -0.0664(7) 0.3963(6) -0.1253(6) 0.0272(16) Uani 1 1 d . . . H13 H -0.0500 0.4849 -0.1182 0.033 Uiso 1 1 calc R . . C14 C -0.1976(6) 0.3365(6) -0.1871(5) 0.0228(15) Uani 1 1 d . . . H14 H -0.2713 0.3835 -0.2203 0.027 Uiso 1 1 calc R . . C15 C -0.2211(6) 0.2071(6) -0.2005(5) 0.0225(15) Uani 1 1 d . . . H15 H -0.3110 0.1652 -0.2437 0.027 Uiso 1 1 calc R . . C16 C -0.1140(6) 0.1393(6) -0.1512(5) 0.0202(14) Uani 1 1 d . . . H16 H -0.1307 0.0507 -0.1627 0.024 Uiso 1 1 calc R . . C17 C 0.4641(6) 0.1126(5) 0.2734(5) 0.0185(14) Uani 1 1 d . . . C18 C 0.5754(6) 0.1015(5) 0.3868(5) 0.0164(13) Uani 1 1 d . . . C19 C 0.5554(6) 0.1813(6) 0.4670(6) 0.0218(15) Uani 1 1 d . . . H19 H 0.6100 0.1937 0.5507 0.026 Uiso 1 1 calc R . . C20 C 0.4419(6) 0.2414(5) 0.4057(5) 0.0187(14) Uani 1 1 d . . . C21 C 0.6791(6) 0.0211(6) 0.4078(6) 0.0207(14) Uani 1 1 d . . . C22 C 0.7521(6) -0.0109(6) 0.5241(6) 0.0204(14) Uani 1 1 d . . . H22 H 0.7356 0.0248 0.5886 0.025 Uiso 1 1 calc R . . C23 C 0.8466(6) -0.0922(6) 0.5479(6) 0.0219(15) Uani 1 1 d . . . H23 H 0.8935 -0.1124 0.6280 0.026 Uiso 1 1 calc R . . C24 C 0.8748(6) -0.1460(6) 0.4549(6) 0.0206(14) Uani 1 1 d . . . C25 C 0.8070(6) -0.1085(6) 0.3391(6) 0.0216(15) Uani 1 1 d . . . H25 H 0.8265 -0.1402 0.2747 0.026 Uiso 1 1 calc R . . C26 C 0.7126(6) -0.0264(6) 0.3176(6) 0.0225(15) Uani 1 1 d . . . H26 H 0.6693 -0.0018 0.2387 0.027 Uiso 1 1 calc R . . C27 C 0.3928(6) 0.3318(5) 0.4666(6) 0.0190(14) Uani 1 1 d . . . C28 C 0.3244(6) 0.4283(6) 0.4121(6) 0.0209(14) Uani 1 1 d . . . H28 H 0.3010 0.4353 0.3289 0.025 Uiso 1 1 calc R . . C29 C 0.2896(6) 0.5139(6) 0.4762(6) 0.0260(15) Uani 1 1 d . . . H29 H 0.2420 0.5793 0.4371 0.031 Uiso 1 1 calc R . . C30 C 0.3231(7) 0.5059(6) 0.5972(6) 0.0279(16) Uani 1 1 d . . . H30 H 0.3009 0.5669 0.6418 0.033 Uiso 1 1 calc R . . C31 C 0.3897(7) 0.4081(6) 0.6535(6) 0.0286(16) Uani 1 1 d . . . H31 H 0.4107 0.4004 0.7363 0.034 Uiso 1 1 calc R . . C32 C 0.4249(6) 0.3230(6) 0.5895(6) 0.0245(15) Uani 1 1 d . . . H32 H 0.4716 0.2571 0.6286 0.029 Uiso 1 1 calc R . . C33 C 1.0353(7) -0.2672(7) 0.5952(6) 0.0353(18) Uani 1 1 d . . . H33A H 1.0869 -0.1919 0.6472 0.053 Uiso 1 1 calc R . . H33B H 1.0985 -0.3249 0.5935 0.053 Uiso 1 1 calc R . . H33C H 0.9709 -0.3076 0.6263 0.053 Uiso 1 1 calc R . . C34 C 0.9772(8) -0.2956(7) 0.3765(7) 0.0367(19) Uani 1 1 d . . . H34A H 0.8874 -0.3222 0.3117 0.055 Uiso 1 1 calc R . . H34B H 1.0233 -0.3688 0.4038 0.055 Uiso 1 1 calc R . . H34C H 1.0322 -0.2384 0.3468 0.055 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 B 0.011(4) 0.020(4) 0.016(4) 0.001(3) 0.000(3) 0.002(3) F1 0.0153(19) 0.033(2) 0.023(2) -0.0013(16) 0.0046(16) 0.0078(16) F2 0.025(2) 0.0196(19) 0.024(2) 0.0019(15) 0.0030(16) 0.0043(15) N1 0.014(3) 0.024(3) 0.015(3) 0.002(2) 0.004(2) 0.005(2) N2 0.016(3) 0.018(3) 0.020(3) 0.004(2) 0.008(2) 0.004(2) N3 0.017(3) 0.018(3) 0.019(3) 0.001(2) 0.008(2) 0.006(2) N4 0.026(3) 0.039(3) 0.022(3) 0.011(3) 0.011(3) 0.019(3) C1 0.017(3) 0.020(3) 0.018(3) 0.001(3) 0.006(3) 0.001(3) C2 0.019(3) 0.021(3) 0.020(3) 0.004(3) 0.010(3) 0.004(3) C3 0.017(3) 0.024(3) 0.013(3) 0.002(3) 0.003(3) 0.002(3) C4 0.017(3) 0.016(3) 0.018(3) 0.000(3) 0.012(3) 0.002(3) C5 0.024(4) 0.019(3) 0.016(3) 0.005(3) 0.008(3) 0.004(3) C6 0.023(4) 0.026(4) 0.020(4) 0.005(3) 0.001(3) 0.006(3) C7 0.030(4) 0.023(4) 0.025(4) -0.005(3) 0.005(3) 0.001(3) C8 0.043(4) 0.021(4) 0.031(4) 0.000(3) 0.017(3) 0.014(3) C9 0.026(4) 0.028(4) 0.035(4) 0.003(3) 0.013(3) 0.008(3) C10 0.025(4) 0.025(4) 0.023(4) 0.003(3) 0.010(3) 0.007(3) C11 0.021(3) 0.021(3) 0.013(3) 0.002(3) 0.006(3) 0.006(3) C12 0.026(4) 0.020(3) 0.020(4) 0.002(3) 0.003(3) 0.005(3) C13 0.032(4) 0.022(4) 0.027(4) 0.006(3) 0.009(3) 0.009(3) C14 0.024(4) 0.025(4) 0.019(3) 0.008(3) 0.007(3) 0.012(3) C15 0.019(3) 0.031(4) 0.017(3) 0.006(3) 0.006(3) 0.006(3) C16 0.024(4) 0.021(3) 0.018(3) 0.007(3) 0.010(3) 0.008(3) C17 0.019(3) 0.017(3) 0.022(4) 0.007(3) 0.009(3) 0.007(3) C18 0.010(3) 0.015(3) 0.019(3) 0.001(3) 0.000(3) 0.000(2) C19 0.026(4) 0.018(3) 0.019(3) 0.001(3) 0.006(3) 0.004(3) C20 0.014(3) 0.017(3) 0.020(3) -0.001(3) 0.003(3) -0.001(3) C21 0.017(3) 0.020(3) 0.023(4) 0.003(3) 0.006(3) 0.001(3) C22 0.017(3) 0.023(3) 0.018(3) -0.001(3) 0.004(3) 0.002(3) C23 0.019(3) 0.029(4) 0.015(3) 0.003(3) 0.004(3) 0.003(3) C24 0.012(3) 0.025(4) 0.023(4) 0.007(3) 0.004(3) 0.005(3) C25 0.016(3) 0.032(4) 0.019(3) 0.004(3) 0.007(3) 0.008(3) C26 0.013(3) 0.036(4) 0.014(3) 0.003(3) 0.000(3) 0.006(3) C27 0.016(3) 0.016(3) 0.023(3) -0.004(3) 0.007(3) -0.004(3) C28 0.014(3) 0.023(4) 0.021(3) -0.001(3) 0.003(3) 0.002(3) C29 0.016(3) 0.028(4) 0.032(4) 0.004(3) 0.007(3) 0.006(3) C30 0.026(4) 0.025(4) 0.034(4) -0.005(3) 0.015(3) 0.004(3) C31 0.033(4) 0.034(4) 0.019(4) -0.005(3) 0.013(3) 0.002(3) C32 0.024(4) 0.024(4) 0.025(4) 0.002(3) 0.008(3) 0.007(3) C33 0.028(4) 0.047(5) 0.032(4) 0.015(4) 0.008(3) 0.022(4) C34 0.037(4) 0.046(5) 0.038(4) 0.012(4) 0.020(4) 0.026(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 B F1 1.371(8) . ? B F2 1.384(8) . ? B N3 1.568(8) . ? B N2 1.569(8) . ? N1 C17 1.314(8) . ? N1 C1 1.334(8) . ? N2 C4 1.362(8) . ? N2 C1 1.395(8) . ? N3 C20 1.355(8) . ? N3 C17 1.387(7) . ? N4 C24 1.356(8) . ? N4 C34 1.436(9) . ? N4 C33 1.451(8) . ? C1 C2 1.409(9) . ? C2 C3 1.376(8) . ? C2 C5 1.462(8) . ? C3 C4 1.391(8) . ? C3 H3 0.9500 . ? C4 C11 1.462(8) . ? C5 C10 1.392(9) . ? C5 C6 1.394(9) . ? C6 C7 1.376(9) . ? C6 H6 0.9500 . ? C7 C8 1.371(9) . ? C7 H7 0.9500 . ? C8 C9 1.383(9) . ? C8 H8 0.9500 . ? C9 C10 1.392(9) . ? C9 H9 0.9500 . ? C10 H10 0.9500 . ? C11 C12 1.393(9) . ? C11 C16 1.415(9) . ? C12 C13 1.390(9) . ? C12 H12 0.9500 . ? C13 C14 1.380(9) . ? C13 H13 0.9500 . ? C14 C15 1.387(9) . ? C14 H14 0.9500 . ? C15 C16 1.379(9) . ? C15 H15 0.9500 . ? C16 H16 0.9500 . ? C17 C18 1.447(8) . ? C18 C19 1.380(9) . ? C18 C21 1.441(8) . ? C19 C20 1.401(9) . ? C19 H19 0.9500 . ? C20 C27 1.473(8) . ? C21 C26 1.384(9) . ? C21 C22 1.399(9) . ? C22 C23 1.371(9) . ? C22 H22 0.9500 . ? C23 C24 1.407(9) . ? C23 H23 0.9500 . ? C24 C25 1.406(8) . ? C25 C26 1.378(9) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 C28 1.380(9) . ? C27 C32 1.406(9) . ? C28 C29 1.368(9) . ? C28 H28 0.9500 . ? C29 C30 1.378(9) . ? C29 H29 0.9500 . ? C30 C31 1.392(9) . ? C30 H30 0.9500 . ? C31 C32 1.365(9) . ? C31 H31 0.9500 . ? C32 H32 0.9500 . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? 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 B F2 111.5(5) . . ? F1 B N3 111.4(5) . . ? F2 B N3 108.8(5) . . ? F1 B N2 109.5(5) . . ? F2 B N2 110.1(5) . . ? N3 B N2 105.4(5) . . ? C17 N1 C1 119.4(5) . . ? C4 N2 C1 106.4(5) . . ? C4 N2 B 129.7(5) . . ? C1 N2 B 122.7(5) . . ? C20 N3 C17 106.6(5) . . ? C20 N3 B 131.2(5) . . ? C17 N3 B 122.2(5) . . ? C24 N4 C34 120.7(5) . . ? C24 N4 C33 120.6(5) . . ? C34 N4 C33 118.7(5) . . ? N1 C1 N2 123.9(5) . . ? N1 C1 C2 126.0(5) . . ? N2 C1 C2 109.8(5) . . ? C3 C2 C1 105.2(5) . . ? C3 C2 C5 127.6(6) . . ? C1 C2 C5 126.9(6) . . ? C2 C3 C4 109.3(5) . . ? C2 C3 H3 125.3 . . ? C4 C3 H3 125.3 . . ? N2 C4 C3 109.2(5) . . ? N2 C4 C11 125.4(5) . . ? C3 C4 C11 125.3(6) . . ? C10 C5 C6 118.8(6) . . ? C10 C5 C2 121.9(6) . . ? C6 C5 C2 119.4(6) . . ? C7 C6 C5 120.2(6) . . ? C7 C6 H6 119.9 . . ? C5 C6 H6 119.9 . . ? C8 C7 C6 121.1(6) . . ? C8 C7 H7 119.5 . . ? C6 C7 H7 119.5 . . ? C7 C8 C9 119.6(6) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C8 C9 C10 120.0(6) . . ? C8 C9 H9 120.0 . . ? C10 C9 H9 120.0 . . ? C9 C10 C5 120.3(6) . . ? C9 C10 H10 119.8 . . ? C5 C10 H10 119.8 . . ? C12 C11 C16 117.8(6) . . ? C12 C11 C4 124.8(6) . . ? C16 C11 C4 117.4(5) . . ? C13 C12 C11 120.4(6) . . ? C13 C12 H12 119.8 . . ? C11 C12 H12 119.8 . . ? C14 C13 C12 121.1(6) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C13 C14 C15 119.5(6) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? C16 C15 C14 120.0(6) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C15 C16 C11 121.2(6) . . ? C15 C16 H16 119.4 . . ? C11 C16 H16 119.4 . . ? N1 C17 N3 124.8(5) . . ? N1 C17 C18 124.7(5) . . ? N3 C17 C18 109.9(5) . . ? C19 C18 C21 129.4(6) . . ? C19 C18 C17 104.1(5) . . ? C21 C18 C17 126.4(6) . . ? C18 C19 C20 109.3(6) . . ? C18 C19 H19 125.4 . . ? C20 C19 H19 125.4 . . ? N3 C20 C19 110.0(5) . . ? N3 C20 C27 127.4(5) . . ? C19 C20 C27 122.6(6) . . ? C26 C21 C22 117.1(6) . . ? C26 C21 C18 123.1(6) . . ? C22 C21 C18 119.8(6) . . ? C23 C22 C21 122.1(6) . . ? C23 C22 H22 119.0 . . ? C21 C22 H22 119.0 . . ? C22 C23 C24 120.7(6) . . ? C22 C23 H23 119.7 . . ? C24 C23 H23 119.7 . . ? N4 C24 C25 120.8(6) . . ? N4 C24 C23 121.8(6) . . ? C25 C24 C23 117.3(6) . . ? C26 C25 C24 120.8(6) . . ? C26 C25 H25 119.6 . . ? C24 C25 H25 119.6 . . ? C25 C26 C21 121.9(6) . . ? C25 C26 H26 119.0 . . ? C21 C26 H26 119.0 . . ? C28 C27 C32 118.3(6) . . ? C28 C27 C20 124.1(6) . . ? C32 C27 C20 117.5(5) . . ? C29 C28 C27 121.0(6) . . ? C29 C28 H28 119.5 . . ? C27 C28 H28 119.5 . . ? C28 C29 C30 120.5(6) . . ? C28 C29 H29 119.7 . . ? C30 C29 H29 119.7 . . ? C29 C30 C31 119.5(6) . . ? C29 C30 H30 120.2 . . ? C31 C30 H30 120.2 . . ? C32 C31 C30 119.9(6) . . ? C32 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C31 C32 C27 120.8(6) . . ? C31 C32 H32 119.6 . . ? C27 C32 H32 119.6 . . ? N4 C33 H33A 109.5 . . ? N4 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? N4 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? N4 C34 H34A 109.5 . . ? N4 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? N4 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 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 F1 B N2 C4 42.6(8) . . . . ? F2 B N2 C4 -80.3(7) . . . . ? N3 B N2 C4 162.5(5) . . . . ? F1 B N2 C1 -123.2(6) . . . . ? F2 B N2 C1 114.0(6) . . . . ? N3 B N2 C1 -3.2(7) . . . . ? F1 B N3 C20 -51.1(8) . . . . ? F2 B N3 C20 72.3(8) . . . . ? N2 B N3 C20 -169.7(6) . . . . ? F1 B N3 C17 130.9(6) . . . . ? F2 B N3 C17 -105.8(6) . . . . ? N2 B N3 C17 12.3(7) . . . . ? C17 N1 C1 N2 6.9(9) . . . . ? C17 N1 C1 C2 -166.7(6) . . . . ? C4 N2 C1 N1 -174.7(6) . . . . ? B N2 C1 N1 -6.1(9) . . . . ? C4 N2 C1 C2 -0.3(7) . . . . ? B N2 C1 C2 168.3(5) . . . . ? N1 C1 C2 C3 174.1(6) . . . . ? N2 C1 C2 C3 -0.2(7) . . . . ? N1 C1 C2 C5 -0.6(10) . . . . ? N2 C1 C2 C5 -174.9(6) . . . . ? C1 C2 C3 C4 0.6(7) . . . . ? C5 C2 C3 C4 175.2(6) . . . . ? C1 N2 C4 C3 0.6(6) . . . . ? B N2 C4 C3 -166.9(6) . . . . ? C1 N2 C4 C11 -176.7(6) . . . . ? B N2 C4 C11 15.8(10) . . . . ? C2 C3 C4 N2 -0.8(7) . . . . ? C2 C3 C4 C11 176.5(6) . . . . ? C3 C2 C5 C10 154.5(6) . . . . ? C1 C2 C5 C10 -32.0(10) . . . . ? C3 C2 C5 C6 -27.1(10) . . . . ? C1 C2 C5 C6 146.4(6) . . . . ? C10 C5 C6 C7 -1.0(9) . . . . ? C2 C5 C6 C7 -179.5(6) . . . . ? C5 C6 C7 C8 0.4(10) . . . . ? C6 C7 C8 C9 0.2(11) . . . . ? C7 C8 C9 C10 -0.1(10) . . . . ? C8 C9 C10 C5 -0.5(10) . . . . ? C6 C5 C10 C9 1.1(9) . . . . ? C2 C5 C10 C9 179.5(6) . . . . ? N2 C4 C11 C12 35.2(9) . . . . ? C3 C4 C11 C12 -141.7(7) . . . . ? N2 C4 C11 C16 -147.2(6) . . . . ? C3 C4 C11 C16 35.9(9) . . . . ? C16 C11 C12 C13 1.4(9) . . . . ? C4 C11 C12 C13 178.9(6) . . . . ? C11 C12 C13 C14 0.9(10) . . . . ? C12 C13 C14 C15 -2.0(10) . . . . ? C13 C14 C15 C16 0.6(9) . . . . ? C14 C15 C16 C11 1.7(9) . . . . ? C12 C11 C16 C15 -2.7(9) . . . . ? C4 C11 C16 C15 179.6(6) . . . . ? C1 N1 C17 N3 3.2(9) . . . . ? C1 N1 C17 C18 173.5(6) . . . . ? C20 N3 C17 N1 167.8(6) . . . . ? B N3 C17 N1 -13.7(9) . . . . ? C20 N3 C17 C18 -3.7(7) . . . . ? B N3 C17 C18 174.8(5) . . . . ? N1 C17 C18 C19 -167.9(6) . . . . ? N3 C17 C18 C19 3.6(7) . . . . ? N1 C17 C18 C21 10.5(10) . . . . ? N3 C17 C18 C21 -178.0(6) . . . . ? C21 C18 C19 C20 179.6(6) . . . . ? C17 C18 C19 C20 -2.2(7) . . . . ? C17 N3 C20 C19 2.3(7) . . . . ? B N3 C20 C19 -176.0(6) . . . . ? C17 N3 C20 C27 -177.0(6) . . . . ? B N3 C20 C27 4.7(10) . . . . ? C18 C19 C20 N3 0.0(7) . . . . ? C18 C19 C20 C27 179.3(5) . . . . ? C19 C18 C21 C26 -160.6(7) . . . . ? C17 C18 C21 C26 21.5(10) . . . . ? C19 C18 C21 C22 18.7(10) . . . . ? C17 C18 C21 C22 -159.2(6) . . . . ? C26 C21 C22 C23 -4.2(9) . . . . ? C18 C21 C22 C23 176.5(6) . . . . ? C21 C22 C23 C24 0.6(10) . . . . ? C34 N4 C24 C25 -4.2(10) . . . . ? C33 N4 C24 C25 177.0(6) . . . . ? C34 N4 C24 C23 173.8(6) . . . . ? C33 N4 C24 C23 -5.0(10) . . . . ? C22 C23 C24 N4 -175.3(6) . . . . ? C22 C23 C24 C25 2.8(9) . . . . ? N4 C24 C25 C26 175.4(6) . . . . ? C23 C24 C25 C26 -2.7(9) . . . . ? C24 C25 C26 C21 -0.9(10) . . . . ? C22 C21 C26 C25 4.3(9) . . . . ? C18 C21 C26 C25 -176.4(6) . . . . ? N3 C20 C27 C28 -28.9(10) . . . . ? C19 C20 C27 C28 151.9(6) . . . . ? N3 C20 C27 C32 154.9(6) . . . . ? C19 C20 C27 C32 -24.3(9) . . . . ? C32 C27 C28 C29 0.6(9) . . . . ? C20 C27 C28 C29 -175.6(6) . . . . ? C27 C28 C29 C30 0.4(10) . . . . ? C28 C29 C30 C31 -1.7(10) . . . . ? C29 C30 C31 C32 1.9(10) . . . . ? C30 C31 C32 C27 -1.0(10) . . . . ? C28 C27 C32 C31 -0.3(9) . . . . ? C20 C27 C32 C31 176.2(6) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.379 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.083