Supplementary Material (ESI) for Dalton Transactions This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _audit_creation_date 10-05-05 _publ_contact_author_name 'Raymond Ziessel' _publ_contact_author_address ; Laboratoire de Chimie Universit\'e Louis Pasteur, d'Electronique et de Photonique Moleculaires ECPM, 1 rue Blaise Pascal Strasbourg F-67008 FRANCE ; _publ_contact_author_phone 0390241593 _publ_contact_author_fax 0390241232 _publ_contact_author_email ZIESSEL@CHIMIE.U-STRASBG.FR _publ_contact_letter ; ; _publ_requested_category FM _publ_section_title ; Syntheses and properties of Urea and Thiourea-Substituted Boron Dipyrromethene Dyes as Fluorescent Probes ; loop_ _publ_author_name _publ_author_address 'Ziessel, Raymond' ; Laboratoire de Chimie Mol\'eculaire, Ecole de Chimie, Polym\`eres, Mat\'eriaux (ECPM), Universite Louis Pasteur (ULP), 25 rue Becquerel 67087 Strasbourg Cedex 02 France ; L.Bonardi ; Laboratoire de Chimie Mol\'eculaire, Ecole de Chimie, Polym\`eres, Mat\'eriaux (ECPM), Universite Louis Pasteur (ULP), 25 rue Becquerel 67087 Strasbourg Cedex 02 France ; P.Retailleau ; ICSN-CNRS 1 avenue de la Terrasse 91198 Gif sur Yvette France ; G.Ulrich ; Laboratoire de Chimie Mol\'eculaire, Ecole de Chimie, Polym\`eres, Mat\'eriaux (ECPM), Universite Louis Pasteur (ULP), 25 rue Becquerel 67087 Strasbourg Cedex 02 France ; _publ_section_abstract ; ? ; _publ_section_comment ; ? ; _publ_section_exptl_prep ; ? ; _publ_section_exptl_refinement ; ? ; _publ_section_references ; A.L. Spek, (2005) PLATON 2005, Utrecht University, The Netherland. Sheldrick, G.M. (1997). SHELXL97. Program for the refinement of crystal structures. University of Gottingen. Germany. ; _publ_section_figure_captions ; ? ; _publ_section_acknowledgements ; ? ; data_lb128 _database_code_depnum_ccdc_archive 'CCDC 289577' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H25 B F2 N4 O4' _chemical_formula_sum 'C23 H25 B F2 N4 O4' _chemical_formula_weight 470.28 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' B B .0090 .0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F .0727 .0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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 13.345(3) _cell_length_b 8.431(4) _cell_length_c 41.094(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4624(2) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.7 _cell_measurement_theta_max 19.0 _exptl_crystal_description plate _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1968 _exptl_absorpt_coefficient_mu 0.870 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type Cuk\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_source 'Enraf Nonius FR590' _diffrn_detector 'scintillation LiI' _diffrn_detector_dtime 1.195 _diffrn_measurement_device '\k-geometry diffractometer' _diffrn_measurement_device_type 'Enraf Nonius CAD4' _diffrn_measurement_method 'non-profiled omega/2theta scans' _diffrn_standards_number 3 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l -1 3 3 3 -3 1 2 1 -5 _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 2 _diffrn_standards_decay_corr_max 1.028 _diffrn_standards_decay_corr_min 0.976 _diffrn_orient_matrix_type ; x-axis points to radiation source the matrix is specified in reciprocal space ; _diffrn_orient_matrix_UB_11 0.015427 _diffrn_orient_matrix_UB_12 0.033979 _diffrn_orient_matrix_UB_13 -0.021401 _diffrn_orient_matrix_UB_21 0.011558 _diffrn_orient_matrix_UB_22 0.065847 _diffrn_orient_matrix_UB_23 0.011373 _diffrn_orient_matrix_UB_31 0.117057 _diffrn_orient_matrix_UB_32 -0.011000 _diffrn_orient_matrix_UB_33 0.001724 _diffrn_reflns_number 7816 _diffrn_reflns_av_R_equivalents 0.0556 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 3 _diffrn_reflns_limit_k_min -3 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -2 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 67.15 _reflns_number_total 4109 _reflns_number_gt 2958 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 Express (Enraf Nonius, 1994)' _computing_cell_refinement 'CAD4 Express (Enraf Nonius, 1994)' _computing_data_reduction 'XCAD4 (Harms & Wocadlo, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1980-2004)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0814P)^2^+0.9651P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4109 _refine_ls_number_parameters 312 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0760 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1529 _refine_ls_wR_factor_gt 0.1363 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.035 _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 0.4569(2) 0.6551(3) 0.05922(6) 0.0491(6) Uani 1 1 d . . . F1 F 0.42637(13) 0.7631(2) 0.03589(3) 0.0827(5) Uani 1 1 d . . . F2 F 0.45360(11) 0.50279(19) 0.04661(4) 0.0769(5) Uani 1 1 d . . . O3 O 0.6929(2) 0.4163(4) 0.21712(7) 0.1136(9) Uani 1 1 d . . . O4 O 0.6560(2) 0.5403(4) 0.26124(6) 0.1255(11) Uani 1 1 d . . . O1 O 0.58477(19) 1.1068(4) 0.24856(5) 0.1128(9) Uani 1 1 d . . . O2 O 0.5293(2) 1.1918(3) 0.20258(7) 0.1141(9) Uani 1 1 d . . . N1A N 0.56174(19) 1.0882(4) 0.22039(6) 0.0810(8) Uani 1 1 d . . . N2A N 0.65724(19) 0.5277(4) 0.23182(7) 0.0871(9) Uani 1 1 d . . . N1 N 0.56451(13) 0.6938(2) 0.07055(4) 0.0435(4) Uani 1 1 d . . . N2 N 0.38832(13) 0.6663(2) 0.08923(4) 0.0422(4) Uani 1 1 d . . . C1 C 0.59312(15) 0.7232(2) 0.10271(5) 0.0406(5) Uani 1 1 d . . . C2 C 0.69827(17) 0.7541(3) 0.10283(5) 0.0471(5) Uani 1 1 d . . . C10 C 0.76470(19) 0.7966(4) 0.13092(6) 0.0641(7) Uani 1 1 d . . . H10A H 0.8271 0.8374 0.1229 0.077 Uiso 1 1 calc R . . H10B H 0.7771 0.7038 0.1439 0.077 Uiso 1 1 calc R . . H10C H 0.7324 0.8758 0.1440 0.077 Uiso 1 1 calc R . . C3 C 0.73061(18) 0.7438(3) 0.07089(6) 0.0516(6) Uani 1 1 d . . . C11 C 0.8346(2) 0.7722(3) 0.05796(7) 0.0652(7) Uani 1 1 d . . . H11A H 0.8673 0.8508 0.0715 0.075 Uiso 1 1 calc R . . H11B H 0.8294 0.8159 0.0362 0.075 Uiso 1 1 calc R . . C12 C 0.8996(2) 0.6259(4) 0.05671(11) 0.1040(12) Uani 1 1 d . . . H12A H 0.9657 0.6546 0.0496 0.125 Uiso 1 1 calc R . . H12B H 0.8712 0.5509 0.0418 0.125 Uiso 1 1 calc R . . H12C H 0.9034 0.5793 0.0780 0.125 Uiso 1 1 calc R . . C4 C 0.64672(18) 0.7058(3) 0.05161(5) 0.0508(5) Uani 1 1 d . . . C1B C 0.6427(2) 0.6847(4) 0.01590(6) 0.0730(8) Uani 1 1 d . . . H1BA H 0.6050 0.5909 0.0108 0.088 Uiso 1 1 calc R . . H1BB H 0.7095 0.6743 0.0075 0.088 Uiso 1 1 calc R . . H1BC H 0.6109 0.7752 0.0062 0.088 Uiso 1 1 calc R . . C9 C 0.52083(15) 0.7221(2) 0.12727(4) 0.0382(4) Uani 1 1 d . . . C8 C 0.41959(16) 0.6953(2) 0.12116(4) 0.0389(5) Uani 1 1 d . . . C7 C 0.33361(16) 0.6870(2) 0.14167(5) 0.0432(5) Uani 1 1 d . . . C13 C 0.32706(19) 0.7066(4) 0.17778(6) 0.0633(7) Uani 1 1 d . . . H13A H 0.2604 0.6818 0.1849 0.076 Uiso 1 1 calc R . . H13B H 0.3428 0.8142 0.1835 0.076 Uiso 1 1 calc R . . H13C H 0.3738 0.6363 0.1881 0.076 Uiso 1 1 calc R . . C6 C 0.25278(17) 0.6526(3) 0.12181(5) 0.0460(5) Uani 1 1 d . . . C14 C 0.14548(17) 0.6308(3) 0.13172(6) 0.0556(6) Uani 1 1 d . . . H14A H 0.1434 0.5945 0.1541 0.064 Uiso 1 1 calc R . . H14B H 0.1157 0.5488 0.1183 0.064 Uiso 1 1 calc R . . C15 C 0.0838(2) 0.7793(3) 0.12877(9) 0.0819(9) Uani 1 1 d . . . H15A H 0.0856 0.8164 0.1067 0.098 Uiso 1 1 calc R . . H15B H 0.1105 0.8595 0.1429 0.098 Uiso 1 1 calc R . . H15C H 0.0157 0.7570 0.1348 0.098 Uiso 1 1 calc R . . C5 C 0.28854(16) 0.6394(3) 0.08975(5) 0.0469(5) Uani 1 1 d . . . C1C C 0.2298(2) 0.6009(4) 0.06003(6) 0.0698(7) Uani 1 1 d . . . H1CA H 0.2745 0.5899 0.0419 0.084 Uiso 1 1 calc R . . H1CB H 0.1829 0.6847 0.0558 0.084 Uiso 1 1 calc R . . H1CC H 0.1942 0.5033 0.0633 0.084 Uiso 1 1 calc R . . C1A C 0.55269(15) 0.7509(3) 0.16156(5) 0.0429(5) Uani 1 1 d . . . C2A C 0.54531(16) 0.9022(3) 0.17469(5) 0.0482(5) Uani 1 1 d . . . H2A H 0.5234 0.9864 0.1619 0.055 Uiso 1 1 calc R . . C3A C 0.57086(18) 0.9263(3) 0.20687(5) 0.0580(6) Uani 1 1 d . . . C4A C 0.60517(18) 0.8061(4) 0.22646(6) 0.0651(8) Uani 1 1 d . . . H4A H 0.6207 0.8234 0.2482 0.075 Uiso 1 1 calc R . . C5A C 0.61550(18) 0.6587(4) 0.21238(6) 0.0600(7) Uani 1 1 d . . . C6A C 0.58949(16) 0.6281(3) 0.18057(5) 0.0521(6) Uani 1 1 d . . . H6A H 0.5965 0.5267 0.1720 0.060 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 0.0574(15) 0.0522(15) 0.0376(11) -0.0048(11) -0.0077(11) 0.0000(12) F1 0.0817(10) 0.1165(14) 0.0500(7) 0.0308(8) -0.0071(7) 0.0128(10) F2 0.0737(9) 0.0791(11) 0.0777(10) -0.0441(8) -0.0047(8) -0.0082(8) O3 0.0946(17) 0.130(2) 0.116(2) 0.0469(18) -0.0047(15) 0.0442(17) O4 0.123(2) 0.188(3) 0.0657(13) 0.0518(16) -0.0280(13) 0.006(2) O1 0.1163(19) 0.152(2) 0.0697(13) -0.0631(15) -0.0162(13) 0.0032(17) O2 0.156(3) 0.0856(17) 0.1005(17) -0.0427(15) -0.0314(18) 0.0164(17) N1A 0.0785(16) 0.103(2) 0.0613(14) -0.0426(15) -0.0089(12) 0.0001(16) N2A 0.0575(14) 0.132(3) 0.0716(17) 0.0420(17) -0.0143(12) 0.0041(16) N1 0.0546(10) 0.0398(9) 0.0361(8) -0.0037(7) 0.0009(8) -0.0028(8) N2 0.0466(9) 0.0422(10) 0.0377(9) -0.0009(7) -0.0076(7) -0.0013(8) C1 0.0470(11) 0.0391(11) 0.0356(9) -0.0023(8) -0.0013(9) 0.0001(9) C2 0.0487(12) 0.0409(11) 0.0519(12) -0.0027(9) 0.0005(10) -0.0030(10) C10 0.0492(13) 0.0757(18) 0.0674(15) -0.0111(14) -0.0051(12) -0.0091(13) C3 0.0568(13) 0.0417(12) 0.0562(12) -0.0012(10) 0.0088(11) -0.0057(11) C11 0.0637(15) 0.0545(15) 0.0774(17) -0.0004(13) 0.0194(13) -0.0109(13) C12 0.0716(19) 0.077(2) 0.163(4) -0.007(2) 0.045(2) 0.0024(17) C4 0.0635(14) 0.0436(12) 0.0453(11) -0.0002(10) 0.0092(11) -0.0039(11) C1B 0.0865(19) 0.086(2) 0.0461(13) -0.0027(13) 0.0145(13) -0.0079(16) C9 0.0435(11) 0.0340(10) 0.0371(9) -0.0015(8) -0.0038(8) 0.0018(9) C8 0.0471(11) 0.0345(10) 0.0350(9) 0.0000(8) -0.0038(8) 0.0008(9) C7 0.0458(11) 0.0404(11) 0.0435(10) 0.0040(9) -0.0012(9) -0.0016(9) C13 0.0554(14) 0.0856(19) 0.0490(12) 0.0005(13) 0.0086(11) -0.0074(14) C6 0.0445(11) 0.0372(11) 0.0563(12) 0.0057(9) -0.0048(10) -0.0008(9) C14 0.0469(12) 0.0479(13) 0.0721(15) 0.0084(11) -0.0047(11) -0.0073(10) C15 0.0544(15) 0.0607(17) 0.130(3) 0.0164(18) 0.0097(16) 0.0057(14) C5 0.0487(12) 0.0407(12) 0.0514(12) 0.0039(9) -0.0125(10) -0.0044(9) C1C 0.0640(15) 0.083(2) 0.0627(15) -0.0049(14) -0.0226(13) -0.0102(15) C1A 0.0393(10) 0.0535(13) 0.0358(9) -0.0032(9) -0.0028(8) -0.0002(9) C2A 0.0458(11) 0.0573(13) 0.0415(10) -0.0096(10) -0.0034(9) 0.0008(10) C3A 0.0510(13) 0.0804(17) 0.0426(11) -0.0178(12) -0.0028(10) -0.0013(13) C4A 0.0516(13) 0.108(2) 0.0353(11) -0.0038(13) -0.0041(10) -0.0102(14) C5A 0.0428(12) 0.090(2) 0.0470(12) 0.0168(13) -0.0065(10) 0.0010(13) C6A 0.0455(12) 0.0636(14) 0.0472(11) 0.0071(11) -0.0041(10) 0.0031(11) _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 1.384(3) . ? B F2 1.385(3) . ? B N2 1.539(3) . ? B N1 1.545(3) . ? O3 N2A 1.214(4) . ? O4 N2A 1.214(3) . ? O1 N1A 1.208(3) . ? O2 N1A 1.219(4) . ? N1A C3A 1.479(4) . ? N2A C5A 1.472(4) . ? N1 C4 1.349(3) . ? N1 C1 1.398(2) . ? N2 C5 1.351(3) . ? N2 C8 1.398(2) . ? C1 C9 1.396(3) . ? C1 C2 1.427(3) . ? C2 C3 1.384(3) . ? C2 C10 1.499(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C3 C4 1.408(3) . ? C3 C11 1.505(3) . ? C11 C12 1.509(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C4 C1B 1.479(3) . ? C1B H1BA 0.9600 . ? C1B H1BB 0.9600 . ? C1B H1BC 0.9600 . ? C9 C8 1.393(3) . ? C9 C1A 1.491(3) . ? C8 C7 1.425(3) . ? C7 C6 1.384(3) . ? C7 C13 1.495(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C6 C5 1.406(3) . ? C6 C14 1.500(3) . ? C14 C15 1.504(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C5 C1C 1.487(3) . ? C1C H1CA 0.9600 . ? C1C H1CB 0.9600 . ? C1C H1CC 0.9600 . ? C1A C6A 1.387(3) . ? C1A C2A 1.389(3) . ? C2A C3A 1.381(3) . ? C2A H2A 0.9300 . ? C3A C4A 1.373(4) . ? C4A C5A 1.378(4) . ? C4A H4A 0.9300 . ? C5A C6A 1.377(3) . ? C6A H6A 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 F1 B F2 109.98(19) . . ? F1 B N2 109.9(2) . . ? F2 B N2 109.8(2) . . ? F1 B N1 110.1(2) . . ? F2 B N1 109.7(2) . . ? N2 B N1 107.36(16) . . ? O1 N1A O2 124.9(3) . . ? O1 N1A C3A 117.3(3) . . ? O2 N1A C3A 117.7(2) . . ? O4 N2A O3 124.6(3) . . ? O4 N2A C5A 118.0(3) . . ? O3 N2A C5A 117.3(3) . . ? C4 N1 C1 108.06(18) . . ? C4 N1 B 126.75(17) . . ? C1 N1 B 125.19(17) . . ? C5 N2 C8 107.99(17) . . ? C5 N2 B 126.04(17) . . ? C8 N2 B 125.83(18) . . ? C9 C1 N1 119.57(18) . . ? C9 C1 C2 132.70(19) . . ? N1 C1 C2 107.70(17) . . ? C3 C2 C1 106.98(19) . . ? C3 C2 C10 124.1(2) . . ? C1 C2 C10 128.9(2) . . ? C2 C10 H10A 109.5 . . ? C2 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C2 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C2 C3 C4 107.4(2) . . ? C2 C3 C11 127.7(2) . . ? C4 C3 C11 124.8(2) . . ? C3 C11 C12 114.4(2) . . ? C3 C11 H11A 108.7 . . ? C12 C11 H11A 108.7 . . ? C3 C11 H11B 108.7 . . ? C12 C11 H11B 108.7 . . ? H11A C11 H11B 107.6 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C4 C3 109.82(19) . . ? N1 C4 C1B 122.2(2) . . ? C3 C4 C1B 127.9(2) . . ? C4 C1B H1BA 109.5 . . ? C4 C1B H1BB 109.5 . . ? H1BA C1B H1BB 109.5 . . ? C4 C1B H1BC 109.5 . . ? H1BA C1B H1BC 109.5 . . ? H1BB C1B H1BC 109.5 . . ? C8 C9 C1 122.75(18) . . ? C8 C9 C1A 118.25(18) . . ? C1 C9 C1A 119.00(18) . . ? C9 C8 N2 119.15(18) . . ? C9 C8 C7 133.01(18) . . ? N2 C8 C7 107.82(17) . . ? C6 C7 C8 106.79(18) . . ? C6 C7 C13 124.3(2) . . ? C8 C7 C13 128.93(19) . . ? C7 C13 H13A 109.5 . . ? C7 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C7 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 C6 C5 107.75(19) . . ? C7 C6 C14 127.6(2) . . ? C5 C6 C14 124.7(2) . . ? C6 C14 C15 113.5(2) . . ? C6 C14 H14A 108.9 . . ? C15 C14 H14A 108.9 . . ? C6 C14 H14B 108.9 . . ? C15 C14 H14B 108.9 . . ? H14A C14 H14B 107.7 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N2 C5 C6 109.64(18) . . ? N2 C5 C1C 122.9(2) . . ? C6 C5 C1C 127.5(2) . . ? C5 C1C H1CA 109.5 . . ? C5 C1C H1CB 109.5 . . ? H1CA C1C H1CB 109.5 . . ? C5 C1C H1CC 109.5 . . ? H1CA C1C H1CC 109.5 . . ? H1CB C1C H1CC 109.5 . . ? C6A C1A C2A 119.45(19) . . ? C6A C1A C9 120.8(2) . . ? C2A C1A C9 119.77(19) . . ? C3A C2A C1A 119.3(2) . . ? C3A C2A H2A 120.3 . . ? C1A C2A H2A 120.3 . . ? C4A C3A C2A 122.4(2) . . ? C4A C3A N1A 119.2(2) . . ? C2A C3A N1A 118.4(2) . . ? C3A C4A C5A 116.9(2) . . ? C3A C4A H4A 121.5 . . ? C5A C4A H4A 121.5 . . ? C6A C5A C4A 122.9(2) . . ? C6A C5A N2A 118.0(3) . . ? C4A C5A N2A 119.1(2) . . ? C5A C6A C1A 119.0(2) . . ? C5A C6A H6A 120.5 . . ? C1A C6A H6A 120.5 . . ? 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 N1 C4 -56.5(3) . . . . ? F2 B N1 C4 64.7(3) . . . . ? N2 B N1 C4 -176.08(19) . . . . ? F1 B N1 C1 123.3(2) . . . . ? F2 B N1 C1 -115.6(2) . . . . ? N2 B N1 C1 3.7(3) . . . . ? F1 B N2 C5 61.0(3) . . . . ? F2 B N2 C5 -60.1(3) . . . . ? N1 B N2 C5 -179.31(19) . . . . ? F1 B N2 C8 -123.8(2) . . . . ? F2 B N2 C8 115.2(2) . . . . ? N1 B N2 C8 -4.1(3) . . . . ? C4 N1 C1 C9 178.34(19) . . . . ? B N1 C1 C9 -1.5(3) . . . . ? C4 N1 C1 C2 -0.1(2) . . . . ? B N1 C1 C2 -179.9(2) . . . . ? C9 C1 C2 C3 -177.8(2) . . . . ? N1 C1 C2 C3 0.4(2) . . . . ? C9 C1 C2 C10 -0.1(4) . . . . ? N1 C1 C2 C10 178.1(2) . . . . ? C1 C2 C3 C4 -0.5(3) . . . . ? C10 C2 C3 C4 -178.4(2) . . . . ? C1 C2 C3 C11 177.7(2) . . . . ? C10 C2 C3 C11 -0.2(4) . . . . ? C2 C3 C11 C12 90.8(3) . . . . ? C4 C3 C11 C12 -91.3(4) . . . . ? C1 N1 C4 C3 -0.2(2) . . . . ? B N1 C4 C3 179.6(2) . . . . ? C1 N1 C4 C1B -178.7(2) . . . . ? B N1 C4 C1B 1.1(4) . . . . ? C2 C3 C4 N1 0.5(3) . . . . ? C11 C3 C4 N1 -177.8(2) . . . . ? C2 C3 C4 C1B 178.9(3) . . . . ? C11 C3 C4 C1B 0.6(4) . . . . ? N1 C1 C9 C8 -1.1(3) . . . . ? C2 C1 C9 C8 176.9(2) . . . . ? N1 C1 C9 C1A 178.95(18) . . . . ? C2 C1 C9 C1A -3.0(4) . . . . ? C1 C9 C8 N2 0.8(3) . . . . ? C1A C9 C8 N2 -179.31(18) . . . . ? C1 C9 C8 C7 179.3(2) . . . . ? C1A C9 C8 C7 -0.8(3) . . . . ? C5 N2 C8 C9 178.16(19) . . . . ? B N2 C8 C9 2.2(3) . . . . ? C5 N2 C8 C7 -0.7(2) . . . . ? B N2 C8 C7 -176.7(2) . . . . ? C9 C8 C7 C6 -178.3(2) . . . . ? N2 C8 C7 C6 0.3(2) . . . . ? C9 C8 C7 C13 0.3(4) . . . . ? N2 C8 C7 C13 178.9(2) . . . . ? C8 C7 C6 C5 0.2(2) . . . . ? C13 C7 C6 C5 -178.5(2) . . . . ? C8 C7 C6 C14 179.7(2) . . . . ? C13 C7 C6 C14 1.0(4) . . . . ? C7 C6 C14 C15 94.5(3) . . . . ? C5 C6 C14 C15 -86.1(3) . . . . ? C8 N2 C5 C6 0.8(2) . . . . ? B N2 C5 C6 176.8(2) . . . . ? C8 N2 C5 C1C -178.7(2) . . . . ? B N2 C5 C1C -2.8(4) . . . . ? C7 C6 C5 N2 -0.6(3) . . . . ? C14 C6 C5 N2 179.8(2) . . . . ? C7 C6 C5 C1C 178.9(2) . . . . ? C14 C6 C5 C1C -0.7(4) . . . . ? C8 C9 C1A C6A 96.2(2) . . . . ? C1 C9 C1A C6A -83.9(3) . . . . ? C8 C9 C1A C2A -83.6(3) . . . . ? C1 C9 C1A C2A 96.3(2) . . . . ? C6A C1A C2A C3A -2.7(3) . . . . ? C9 C1A C2A C3A 177.2(2) . . . . ? C1A C2A C3A C4A 1.1(4) . . . . ? C1A C2A C3A N1A -179.6(2) . . . . ? O1 N1A C3A C4A -0.4(4) . . . . ? O2 N1A C3A C4A -178.7(3) . . . . ? O1 N1A C3A C2A -179.8(2) . . . . ? O2 N1A C3A C2A 2.0(4) . . . . ? C2A C3A C4A C5A 1.4(4) . . . . ? N1A C3A C4A C5A -177.9(2) . . . . ? C3A C4A C5A C6A -2.5(4) . . . . ? C3A C4A C5A N2A 176.7(2) . . . . ? O4 N2A C5A C6A -161.2(3) . . . . ? O3 N2A C5A C6A 20.6(4) . . . . ? O4 N2A C5A C4A 19.5(4) . . . . ? O3 N2A C5A C4A -158.6(3) . . . . ? C4A C5A C6A C1A 1.0(4) . . . . ? N2A C5A C6A C1A -178.2(2) . . . . ? C2A C1A C6A C5A 1.6(3) . . . . ? C9 C1A C6A C5A -178.2(2) . . . . ? _diffrn_measured_fraction_theta_max .996 _diffrn_reflns_theta_full 67.15 _diffrn_measured_fraction_theta_full .996 _refine_diff_density_max .228 _refine_diff_density_min -.277 _refine_diff_density_rms .047