data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Pena-Cabrera, Eduardo' 'Gomez-Duran, Cesar Frnando' 'Garcia-Moreno, Inmaculada' 'Martin, Virginia' 'Sastre, Roberto' 'Bartuelos, Jorge' 'Lopez Arbeloa, F.' 'Lopez Arbeloa, I\~A+-igo' 'Costela, Angel' _publ_contact_author_name 'Pena-Cabrera, Eduardo' _publ_contact_author_email eduardop@quijote.ugto.mx _publ_section_title ; 8-PropargylaminoBODIPY: Unprecedented Blue-emitting Pyrromethene Dye. Synthesis, Photophysics and Laser Properties. ; # Attachment '- 8_PAB_Pena.cif' data_fla01_clm _database_code_depnum_ccdc_archive 'CCDC 750168' #TrackingRef '- 8_PAB_Pena.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 B F2 N3' _chemical_formula_weight 245.04 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' _cell_length_a 20.0082(11) _cell_length_b 10.2344(6) _cell_length_c 21.5661(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4416.1(4) _cell_formula_units_Z 16 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.474 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 0.113 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9777 _exptl_absorpt_correction_T_max 0.9910 _exptl_absorpt_process_details ? _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12327 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0951 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.78 _diffrn_reflns_theta_max 26.50 _reflns_number_total 4553 _reflns_number_gt 2673 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^ > 2\s(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^)+(0.0276P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4553 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0679 _refine_ls_wR_factor_gt 0.0638 _refine_ls_goodness_of_fit_ref 0.792 _refine_ls_restrained_S_all 0.792 _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 C2 C 0.20039(9) 0.54168(19) 0.06619(7) 0.0158(4) Uani 1 1 d . . . H2 H 0.1850 0.6113 0.0408 0.019 Uiso 1 1 calc R . . C3 C 0.25846(9) 0.47154(19) 0.05632(7) 0.0185(4) Uani 1 1 d . . . H3 H 0.2895 0.4841 0.0235 0.022 Uiso 1 1 calc R . . C4 C 0.26292(8) 0.37923(17) 0.10342(7) 0.0158(4) Uani 1 1 d . . . H4 H 0.2976 0.3169 0.1089 0.019 Uiso 1 1 calc R . . C5 C 0.20690(8) 0.39540(18) 0.14098(7) 0.0120(4) Uani 1 1 d . . . C6 C 0.18624(8) 0.32403(17) 0.19514(7) 0.0116(4) Uani 1 1 d . . . C7 C 0.12318(8) 0.35292(17) 0.22341(7) 0.0120(4) Uani 1 1 d . . . C8 C 0.08469(8) 0.29160(18) 0.26920(7) 0.0154(4) Uani 1 1 d . . . H8 H 0.0974 0.2176 0.2930 0.018 Uiso 1 1 calc R . . C9 C 0.02449(8) 0.35901(18) 0.27338(7) 0.0178(4) Uani 1 1 d . . . H9 H -0.0117 0.3393 0.3003 0.021 Uiso 1 1 calc R . . C10 C 0.02725(9) 0.46041(18) 0.23085(7) 0.0170(4) Uani 1 1 d . . . H10 H -0.0072 0.5227 0.2243 0.020 Uiso 1 1 calc R . . C13 C 0.22449(8) 0.15726(18) 0.27308(7) 0.0160(4) Uani 1 1 d . . . H13A H 0.2041 0.2126 0.3057 0.019 Uiso 1 1 calc R . . H13B H 0.2705 0.1354 0.2865 0.019 Uiso 1 1 calc R . . C14 C 0.18551(8) 0.03539(18) 0.26742(7) 0.0142(4) Uani 1 1 d . . . C15 C 0.15521(9) -0.06272(19) 0.26315(7) 0.0196(4) Uani 1 1 d . . . H15 H 0.1308 -0.1419 0.2597 0.024 Uiso 1 1 calc R . . C22 C 0.21333(8) 0.47511(18) 0.40131(7) 0.0141(4) Uani 1 1 d . . . H22 H 0.2417 0.5407 0.3846 0.017 Uiso 1 1 calc R . . C23 C 0.23398(8) 0.35189(18) 0.41953(7) 0.0145(4) Uani 1 1 d . . . H23 H 0.2781 0.3180 0.4169 0.017 Uiso 1 1 calc R . . C24 C 0.17825(8) 0.28714(17) 0.44236(7) 0.0131(4) Uani 1 1 d . . . H24 H 0.1772 0.2009 0.4587 0.016 Uiso 1 1 calc R . . C25 C 0.12362(8) 0.37267(17) 0.43689(7) 0.0101(4) Uani 1 1 d . . . C26 C 0.05278(8) 0.36106(17) 0.44852(7) 0.0096(4) Uani 1 1 d . . . C27 C 0.00813(8) 0.45759(17) 0.42326(7) 0.0105(4) Uani 1 1 d . . . C28 C -0.06141(8) 0.45574(18) 0.41605(7) 0.0137(4) Uani 1 1 d . . . H28 H -0.0911 0.3899 0.4303 0.016 Uiso 1 1 calc R . . C29 C -0.07864(8) 0.56902(18) 0.38397(7) 0.0153(4) Uani 1 1 d . . . H29 H -0.1224 0.5945 0.3720 0.018 Uiso 1 1 calc R . . C30 C -0.02007(8) 0.63766(18) 0.37281(7) 0.0141(4) Uani 1 1 d . . . H30 H -0.0173 0.7190 0.3518 0.017 Uiso 1 1 calc R . . C33 C 0.06107(8) 0.15102(17) 0.50665(7) 0.0148(4) Uani 1 1 d . . . H33A H 0.0324 0.1095 0.5385 0.018 Uiso 1 1 calc R . . H33B H 0.1024 0.1814 0.5273 0.018 Uiso 1 1 calc R . . C34 C 0.07850(8) 0.05339(18) 0.45909(8) 0.0156(4) Uani 1 1 d . . . C35 C 0.09276(9) -0.02250(19) 0.42012(9) 0.0204(4) Uani 1 1 d . . . H35 H 0.1042 -0.0836 0.3887 0.024 Uiso 1 1 calc R . . B1 B 0.11040(10) 0.5602(2) 0.15272(9) 0.0158(5) Uani 1 1 d . . . B21 B 0.10548(10) 0.6140(2) 0.40294(9) 0.0130(5) Uani 1 1 d . . . N1 N 0.16856(7) 0.49622(14) 0.11765(6) 0.0129(3) Uani 1 1 d . . . N11 N 0.08612(7) 0.45791(15) 0.20001(6) 0.0140(3) Uani 1 1 d . . . N12 N 0.22795(7) 0.23199(14) 0.21546(6) 0.0146(3) Uani 1 1 d . . . H12 H 0.2619 0.2139 0.1910 0.018 Uiso 1 1 calc R . . N21 N 0.14679(6) 0.48860(14) 0.41078(5) 0.0103(3) Uani 1 1 d . . . N31 N 0.03263(6) 0.57079(14) 0.39659(6) 0.0114(3) Uani 1 1 d . . . N32 N 0.02609(7) 0.26309(14) 0.48044(6) 0.0127(3) Uani 1 1 d . . . H32 H -0.0174 0.2662 0.4864 0.015 Uiso 1 1 calc R . . F1 F 0.06022(5) 0.59877(10) 0.11289(4) 0.0231(3) Uani 1 1 d . . . F2 F 0.13456(5) 0.67141(10) 0.18465(4) 0.0195(3) Uani 1 1 d . . . F21 F 0.12677(4) 0.68561(10) 0.35169(4) 0.0180(2) Uani 1 1 d . . . F22 F 0.11267(4) 0.69306(10) 0.45667(4) 0.0163(2) 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 C2 0.0208(10) 0.0126(10) 0.0141(9) 0.0043(8) -0.0029(8) -0.0028(9) C3 0.0184(10) 0.0214(11) 0.0158(9) 0.0024(9) 0.0033(8) 0.0001(10) C4 0.0155(10) 0.0134(10) 0.0185(9) 0.0016(9) 0.0017(8) 0.0018(9) C5 0.0110(9) 0.0129(10) 0.0122(8) -0.0009(8) -0.0019(7) -0.0028(8) C6 0.0115(9) 0.0080(9) 0.0154(9) -0.0029(8) -0.0052(7) -0.0035(9) C7 0.0132(9) 0.0108(10) 0.0120(9) -0.0014(8) -0.0019(7) -0.0016(9) C8 0.0169(10) 0.0182(10) 0.0110(9) -0.0019(8) -0.0010(7) -0.0027(9) C9 0.0154(10) 0.0208(11) 0.0171(9) -0.0049(9) 0.0053(8) -0.0043(10) C10 0.0125(9) 0.0151(11) 0.0235(9) -0.0056(9) 0.0019(8) 0.0041(9) C13 0.0170(9) 0.0170(10) 0.0138(9) 0.0033(9) -0.0016(7) -0.0008(9) C14 0.0154(9) 0.0155(10) 0.0117(9) 0.0029(9) 0.0008(7) 0.0034(10) C15 0.0200(10) 0.0146(11) 0.0242(10) 0.0011(9) 0.0039(8) 0.0003(10) C22 0.0105(9) 0.0178(10) 0.0139(9) -0.0020(8) 0.0035(7) -0.0034(9) C23 0.0082(9) 0.0170(10) 0.0184(9) -0.0040(9) 0.0005(7) 0.0026(9) C24 0.0149(9) 0.0098(10) 0.0145(9) -0.0019(8) -0.0025(7) 0.0012(9) C25 0.0106(9) 0.0101(10) 0.0097(8) -0.0018(8) -0.0018(7) -0.0012(8) C26 0.0127(9) 0.0078(9) 0.0084(8) -0.0029(8) 0.0004(7) -0.0022(8) C27 0.0123(9) 0.0096(10) 0.0096(8) -0.0022(8) 0.0003(7) -0.0012(9) C28 0.0128(9) 0.0148(10) 0.0133(9) 0.0003(9) 0.0017(7) -0.0013(9) C29 0.0110(9) 0.0187(11) 0.0162(9) -0.0001(9) -0.0025(7) 0.0048(9) C30 0.0182(10) 0.0118(10) 0.0124(9) 0.0024(8) -0.0036(7) 0.0032(9) C33 0.0138(9) 0.0120(10) 0.0186(9) 0.0051(9) 0.0003(8) 0.0004(9) C34 0.0116(10) 0.0117(10) 0.0237(10) 0.0044(9) -0.0012(8) -0.0008(9) C35 0.0192(10) 0.0142(10) 0.0278(10) 0.0016(10) -0.0012(9) 0.0030(10) B1 0.0126(11) 0.0153(12) 0.0195(11) -0.0005(10) -0.0051(9) -0.0010(10) B21 0.0136(10) 0.0115(11) 0.0140(10) 0.0028(10) 0.0041(9) -0.0004(10) N1 0.0155(8) 0.0108(8) 0.0124(7) 0.0000(6) -0.0020(6) -0.0008(7) N11 0.0114(8) 0.0131(8) 0.0176(7) -0.0022(7) 0.0014(6) 0.0002(8) N12 0.0132(8) 0.0153(8) 0.0153(7) 0.0033(7) 0.0032(6) 0.0009(8) N21 0.0100(7) 0.0095(8) 0.0115(7) 0.0026(6) 0.0007(6) -0.0032(7) N31 0.0119(7) 0.0098(8) 0.0123(7) 0.0014(7) 0.0007(6) 0.0017(7) N32 0.0081(7) 0.0108(8) 0.0191(7) 0.0027(7) 0.0008(6) 0.0003(7) F1 0.0167(5) 0.0233(6) 0.0294(6) 0.0048(5) -0.0070(5) 0.0038(5) F2 0.0178(6) 0.0124(6) 0.0284(6) -0.0050(5) 0.0014(4) -0.0014(5) F21 0.0177(5) 0.0171(6) 0.0192(5) 0.0078(5) 0.0031(4) 0.0000(5) F22 0.0175(5) 0.0123(6) 0.0192(5) -0.0030(5) 0.0001(4) -0.0022(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 C2 N1 1.362(2) . ? C2 C3 1.382(2) . ? C2 H2 0.9500 . ? C3 C4 1.390(2) . ? C3 H3 0.9500 . ? C4 C5 1.393(2) . ? C4 H4 0.9500 . ? C5 N1 1.381(2) . ? C5 C6 1.438(2) . ? C6 N12 1.333(2) . ? C6 C7 1.432(2) . ? C7 N11 1.400(2) . ? C7 C8 1.401(2) . ? C8 C9 1.391(2) . ? C8 H8 0.9500 . ? C9 C10 1.386(2) . ? C9 H9 0.9500 . ? C10 N11 1.353(2) . ? C10 H10 0.9500 . ? C13 N12 1.461(2) . ? C13 C14 1.476(2) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 C15 1.176(2) . ? C15 H15 0.9500 . ? C22 N21 1.354(2) . ? C22 C23 1.384(2) . ? C22 H22 0.9500 . ? C23 C24 1.387(2) . ? C23 H23 0.9500 . ? C24 C25 1.405(2) . ? C24 H24 0.9500 . ? C25 N21 1.393(2) . ? C25 C26 1.444(2) . ? C26 N32 1.328(2) . ? C26 C27 1.439(2) . ? C27 N31 1.383(2) . ? C27 C28 1.400(2) . ? C28 C29 1.393(2) . ? C28 H28 0.9500 . ? C29 C30 1.387(2) . ? C29 H29 0.9500 . ? C30 N31 1.3576(19) . ? C30 H30 0.9500 . ? C33 N32 1.458(2) . ? C33 C34 1.474(3) . ? C33 H33A 0.9900 . ? C33 H33B 0.9900 . ? C34 C35 1.179(2) . ? C35 H35 0.9500 . ? B1 F1 1.379(2) . ? B1 F2 1.416(2) . ? B1 N1 1.535(2) . ? B1 N11 1.540(3) . ? B21 F21 1.393(2) . ? B21 F22 1.421(2) . ? B21 N31 1.529(2) . ? B21 N21 1.536(2) . ? N12 H12 0.8800 . ? N32 H32 0.8800 . ? 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 N1 C2 C3 109.95(15) . . ? N1 C2 H2 125.0 . . ? C3 C2 H2 125.0 . . ? C2 C3 C4 107.12(15) . . ? C2 C3 H3 126.4 . . ? C4 C3 H3 126.4 . . ? C3 C4 C5 107.02(16) . . ? C3 C4 H4 126.5 . . ? C5 C4 H4 126.5 . . ? N1 C5 C4 108.90(15) . . ? N1 C5 C6 121.05(15) . . ? C4 C5 C6 130.03(16) . . ? N12 C6 C7 123.90(15) . . ? N12 C6 C5 116.49(14) . . ? C7 C6 C5 119.60(15) . . ? N11 C7 C8 107.87(14) . . ? N11 C7 C6 118.15(14) . . ? C8 C7 C6 133.78(16) . . ? C9 C8 C7 107.43(15) . . ? C9 C8 H8 126.3 . . ? C7 C8 H8 126.3 . . ? C10 C9 C8 107.09(15) . . ? C10 C9 H9 126.5 . . ? C8 C9 H9 126.5 . . ? N11 C10 C9 110.24(16) . . ? N11 C10 H10 124.9 . . ? C9 C10 H10 124.9 . . ? N12 C13 C14 113.39(13) . . ? N12 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? N12 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C15 C14 C13 179.06(19) . . ? C14 C15 H15 180.0 . . ? N21 C22 C23 110.10(16) . . ? N21 C22 H22 125.0 . . ? C23 C22 H22 125.0 . . ? C22 C23 C24 107.22(15) . . ? C22 C23 H23 126.4 . . ? C24 C23 H23 126.4 . . ? C23 C24 C25 107.32(15) . . ? C23 C24 H24 126.3 . . ? C25 C24 H24 126.3 . . ? N21 C25 C24 107.81(13) . . ? N21 C25 C26 117.83(15) . . ? C24 C25 C26 134.22(16) . . ? N32 C26 C27 117.70(14) . . ? N32 C26 C25 123.13(15) . . ? C27 C26 C25 119.14(15) . . ? N31 C27 C28 108.49(15) . . ? N31 C27 C26 120.83(14) . . ? C28 C27 C26 130.52(17) . . ? C29 C28 C27 106.85(16) . . ? C29 C28 H28 126.6 . . ? C27 C28 H28 126.6 . . ? C30 C29 C28 107.37(15) . . ? C30 C29 H29 126.3 . . ? C28 C29 H29 126.3 . . ? N31 C30 C29 109.59(15) . . ? N31 C30 H30 125.2 . . ? C29 C30 H30 125.2 . . ? N32 C33 C34 112.16(13) . . ? N32 C33 H33A 109.2 . . ? C34 C33 H33A 109.2 . . ? N32 C33 H33B 109.2 . . ? C34 C33 H33B 109.2 . . ? H33A C33 H33B 107.9 . . ? C35 C34 C33 178.50(19) . . ? C34 C35 H35 180.0 . . ? F1 B1 F2 108.75(16) . . ? F1 B1 N1 111.56(14) . . ? F2 B1 N1 108.89(14) . . ? F1 B1 N11 112.18(15) . . ? F2 B1 N11 109.39(14) . . ? N1 B1 N11 105.99(15) . . ? F21 B21 F22 108.45(15) . . ? F21 B21 N31 111.87(14) . . ? F22 B21 N31 109.54(13) . . ? F21 B21 N21 111.25(14) . . ? F22 B21 N21 109.37(14) . . ? N31 B21 N21 106.33(14) . . ? C2 N1 C5 107.01(14) . . ? C2 N1 B1 127.63(15) . . ? C5 N1 B1 124.10(14) . . ? C10 N11 C7 107.37(14) . . ? C10 N11 B1 125.96(16) . . ? C7 N11 B1 126.41(14) . . ? C6 N12 C13 128.33(14) . . ? C6 N12 H12 115.8 . . ? C13 N12 H12 115.8 . . ? C22 N21 C25 107.54(15) . . ? C22 N21 B21 126.71(15) . . ? C25 N21 B21 125.26(13) . . ? C30 N31 C27 107.70(13) . . ? C30 N31 B21 128.93(14) . . ? C27 N31 B21 122.86(14) . . ? C26 N32 C33 127.00(14) . . ? C26 N32 H32 116.5 . . ? C33 N32 H32 116.5 . . ? 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 N1 C2 C3 C4 -0.07(19) . . . . ? C2 C3 C4 C5 0.2(2) . . . . ? C3 C4 C5 N1 -0.20(19) . . . . ? C3 C4 C5 C6 178.59(17) . . . . ? N1 C5 C6 N12 -177.41(14) . . . . ? C4 C5 C6 N12 3.9(3) . . . . ? N1 C5 C6 C7 3.5(2) . . . . ? C4 C5 C6 C7 -175.15(17) . . . . ? N12 C6 C7 N11 175.79(14) . . . . ? C5 C6 C7 N11 -5.2(2) . . . . ? N12 C6 C7 C8 -10.0(3) . . . . ? C5 C6 C7 C8 169.03(17) . . . . ? N11 C7 C8 C9 0.17(18) . . . . ? C6 C7 C8 C9 -174.49(17) . . . . ? C7 C8 C9 C10 -0.53(19) . . . . ? C8 C9 C10 N11 0.7(2) . . . . ? N12 C13 C14 C15 121(12) . . . . ? N21 C22 C23 C24 -1.18(19) . . . . ? C22 C23 C24 C25 0.72(18) . . . . ? C23 C24 C25 N21 -0.02(17) . . . . ? C23 C24 C25 C26 175.44(17) . . . . ? N21 C25 C26 N32 -170.90(14) . . . . ? C24 C25 C26 N32 14.0(3) . . . . ? N21 C25 C26 C27 10.8(2) . . . . ? C24 C25 C26 C27 -164.33(16) . . . . ? N32 C26 C27 N31 171.52(14) . . . . ? C25 C26 C27 N31 -10.1(2) . . . . ? N32 C26 C27 C28 -13.6(3) . . . . ? C25 C26 C27 C28 164.76(16) . . . . ? N31 C27 C28 C29 0.62(18) . . . . ? C26 C27 C28 C29 -174.70(16) . . . . ? C27 C28 C29 C30 -0.51(18) . . . . ? C28 C29 C30 N31 0.22(18) . . . . ? N32 C33 C34 C35 38(7) . . . . ? C3 C2 N1 C5 -0.05(18) . . . . ? C3 C2 N1 B1 167.44(15) . . . . ? C4 C5 N1 C2 0.15(18) . . . . ? C6 C5 N1 C2 -178.76(15) . . . . ? C4 C5 N1 B1 -167.89(15) . . . . ? C6 C5 N1 B1 13.2(2) . . . . ? F1 B1 N1 C2 48.4(2) . . . . ? F2 B1 N1 C2 -71.7(2) . . . . ? N11 B1 N1 C2 170.74(15) . . . . ? F1 B1 N1 C5 -146.13(15) . . . . ? F2 B1 N1 C5 93.83(19) . . . . ? N11 B1 N1 C5 -23.8(2) . . . . ? C9 C10 N11 C7 -0.61(19) . . . . ? C9 C10 N11 B1 -175.01(15) . . . . ? C8 C7 N11 C10 0.27(17) . . . . ? C6 C7 N11 C10 175.89(15) . . . . ? C8 C7 N11 B1 174.64(15) . . . . ? C6 C7 N11 B1 -9.7(2) . . . . ? F1 B1 N11 C10 -42.2(2) . . . . ? F2 B1 N11 C10 78.5(2) . . . . ? N1 B1 N11 C10 -164.22(15) . . . . ? F1 B1 N11 C7 144.40(15) . . . . ? F2 B1 N11 C7 -94.84(19) . . . . ? N1 B1 N11 C7 22.4(2) . . . . ? C7 C6 N12 C13 -9.8(3) . . . . ? C5 C6 N12 C13 171.12(15) . . . . ? C14 C13 N12 C6 89.4(2) . . . . ? C23 C22 N21 C25 1.17(18) . . . . ? C23 C22 N21 B21 173.43(14) . . . . ? C24 C25 N21 C22 -0.70(17) . . . . ? C26 C25 N21 C22 -177.02(13) . . . . ? C24 C25 N21 B21 -173.10(14) . . . . ? C26 C25 N21 B21 10.6(2) . . . . ? F21 B21 N21 C22 38.7(2) . . . . ? F22 B21 N21 C22 -81.11(19) . . . . ? N31 B21 N21 C22 160.69(14) . . . . ? F21 B21 N21 C25 -150.39(14) . . . . ? F22 B21 N21 C25 89.84(18) . . . . ? N31 B21 N21 C25 -28.4(2) . . . . ? C29 C30 N31 C27 0.17(18) . . . . ? C29 C30 N31 B21 -171.70(15) . . . . ? C28 C27 N31 C30 -0.49(18) . . . . ? C26 C27 N31 C30 175.37(14) . . . . ? C28 C27 N31 B21 171.99(14) . . . . ? C26 C27 N31 B21 -12.2(2) . . . . ? F21 B21 N31 C30 -39.0(2) . . . . ? F22 B21 N31 C30 81.3(2) . . . . ? N21 B21 N31 C30 -160.59(14) . . . . ? F21 B21 N31 C27 150.27(15) . . . . ? F22 B21 N31 C27 -89.44(18) . . . . ? N21 B21 N31 C27 28.6(2) . . . . ? C27 C26 N32 C33 175.91(14) . . . . ? C25 C26 N32 C33 -2.4(2) . . . . ? C34 C33 N32 C26 -76.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.243 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.051