# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Herbert Hopfl' _publ_contact_author_email hhopfl@uaem.mx _publ_author_name 'Herbert Hopfl' # Attachment '- Compound 1 solvent-free (861082).cif' data_72herbm _database_code_depnum_ccdc_archive 'CCDC 861082' #TrackingRef '- Compound 1 solvent-free (861082).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H20 B2 N2 O4' _chemical_formula_sum 'C23 H20 B2 N2 O4' _chemical_formula_weight 410.03 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' O O 0.0106 0.0060 '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 Monoclinic _symmetry_space_group_name_H-M C2/c 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 19.867(3) _cell_length_b 9.9419(13) _cell_length_c 13.4309(17) _cell_angle_alpha 90.00 _cell_angle_beta 127.844(2) _cell_angle_gamma 90.00 _cell_volume 2094.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3570 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 28.24 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.98 _exptl_absorpt_correction_T_max 0.99 _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 9818 _diffrn_reflns_av_R_equivalents 0.0703 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1838 _reflns_number_gt 1587 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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. Only weakly diffracting crystals could be grown for this compound, causing higher than usual refinement statistics. ; _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^)+(0.0570P)^2^+14.9977P] 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 1838 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1215 _refine_ls_R_factor_gt 0.1044 _refine_ls_wR_factor_ref 0.2105 _refine_ls_wR_factor_gt 0.2014 _refine_ls_goodness_of_fit_ref 1.202 _refine_ls_restrained_S_all 1.202 _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 B1 B 0.1578(3) 0.4297(5) 0.3129(5) 0.0177(11) Uani 1 1 d . . . N1 N 0.3114(2) 0.8287(4) 0.2561(3) 0.0163(9) Uani 1 1 d . . . O1 O 0.15337(18) 0.3375(3) 0.3905(3) 0.0137(7) Uani 1 1 d . . . O2 O 0.08057(18) 0.4952(3) 0.2139(3) 0.0142(7) Uani 1 1 d . . . C1 C 0.2423(3) 0.7482(4) 0.1764(4) 0.0166(10) Uani 1 1 d . . . H1 H 0.2122 0.7574 0.0881 0.020 Uiso 1 1 calc R . . C2 C 0.2150(3) 0.6552(5) 0.2192(4) 0.0172(10) Uani 1 1 d . . . H2 H 0.1653 0.6038 0.1606 0.021 Uiso 1 1 calc R . . C3 C 0.2602(3) 0.6345(4) 0.3503(4) 0.0146(10) Uani 1 1 d . . . C4 C 0.2363(3) 0.5349(4) 0.4000(4) 0.0160(10) Uani 1 1 d . . . C5 C 0.2857(3) 0.5293(5) 0.5304(4) 0.0208(11) Uani 1 1 d . . . H5 H 0.2716 0.4638 0.5665 0.025 Uiso 1 1 calc R . . C6 C 0.3551(3) 0.6148(5) 0.6124(4) 0.0253(12) Uani 1 1 d . . . H6 H 0.3861 0.6066 0.7010 0.030 Uiso 1 1 calc R . . C7 C 0.3782(3) 0.7093(5) 0.5649(4) 0.0221(11) Uani 1 1 d . . . H7 H 0.4255 0.7668 0.6200 0.026 Uiso 1 1 calc R . . C8 C 0.3308(3) 0.7210(4) 0.4319(4) 0.0166(10) Uani 1 1 d . . . C9 C 0.3535(3) 0.8153(4) 0.3791(4) 0.0150(10) Uani 1 1 d . . . H9 H 0.4012 0.8719 0.4342 0.018 Uiso 1 1 calc R . . C10 C 0.0803(3) 0.2544(4) 0.3237(4) 0.0156(10) Uani 1 1 d . . . H10A H 0.0803 0.1962 0.3835 0.019 Uiso 1 1 calc R . . H10B H 0.0810 0.1959 0.2647 0.019 Uiso 1 1 calc R . . C11 C 0.0000 0.3418(6) 0.2500 0.0141(13) Uani 1 2 d S . . C12 C 0.0022(3) 0.4274(4) 0.1568(4) 0.0140(9) Uani 1 1 d . . . H12A H -0.0086 0.3685 0.0889 0.017 Uiso 1 1 calc R . . H12B H -0.0443 0.4946 0.1175 0.017 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 B1 0.020(3) 0.018(3) 0.023(3) 0.001(2) 0.017(2) 0.000(2) N1 0.019(2) 0.0142(19) 0.017(2) -0.0029(16) 0.0123(17) 0.0006(16) O1 0.0134(15) 0.0127(15) 0.0147(16) 0.0021(12) 0.0085(13) 0.0009(12) O2 0.0147(16) 0.0122(15) 0.0160(16) 0.0021(12) 0.0096(13) -0.0011(13) C1 0.016(2) 0.013(2) 0.021(2) -0.0049(18) 0.012(2) -0.0013(18) C2 0.016(2) 0.017(2) 0.020(2) -0.0008(19) 0.012(2) -0.0029(19) C3 0.019(2) 0.008(2) 0.020(2) 0.0004(17) 0.014(2) 0.0042(18) C4 0.020(2) 0.013(2) 0.019(2) 0.0016(18) 0.014(2) 0.0083(18) C5 0.028(3) 0.017(2) 0.027(3) 0.001(2) 0.021(2) 0.000(2) C6 0.035(3) 0.023(3) 0.015(2) 0.001(2) 0.014(2) -0.001(2) C7 0.026(3) 0.017(2) 0.017(3) -0.0032(19) 0.011(2) -0.004(2) C8 0.017(2) 0.012(2) 0.022(2) -0.0013(18) 0.012(2) 0.0018(18) C9 0.018(2) 0.013(2) 0.013(2) -0.0033(17) 0.009(2) -0.0019(18) C10 0.023(2) 0.014(2) 0.013(2) 0.0010(18) 0.012(2) -0.0001(19) C11 0.021(3) 0.015(3) 0.008(3) 0.000 0.010(3) 0.000 C12 0.014(2) 0.013(2) 0.015(2) 0.0010(18) 0.0087(19) 0.0053(18) _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 O2 1.429(6) . ? B1 O1 1.431(6) . ? B1 C4 1.630(7) . ? B1 N1 1.714(6) 4_545 ? N1 C9 1.323(5) . ? N1 C1 1.366(6) . ? N1 B1 1.714(6) 4 ? O1 C10 1.413(5) . ? O2 C12 1.415(5) . ? C1 C2 1.365(6) . ? C2 C3 1.417(6) . ? C3 C8 1.422(6) . ? C3 C4 1.428(6) . ? C4 C5 1.388(6) . ? C5 C6 1.405(7) . ? C6 C7 1.364(7) . ? C7 C8 1.423(6) . ? C8 C9 1.407(6) . ? C10 C11 1.530(5) . ? C11 C10 1.530(5) 2 ? C11 C12 1.537(5) 2 ? C11 C12 1.537(5) . ? 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 O2 B1 O1 117.4(4) . . ? O2 B1 C4 112.6(4) . . ? O1 B1 C4 110.3(4) . . ? O2 B1 N1 107.5(4) . 4_545 ? O1 B1 N1 102.7(3) . 4_545 ? C4 B1 N1 105.2(3) . 4_545 ? C9 N1 C1 118.7(4) . . ? C9 N1 B1 124.8(4) . 4 ? C1 N1 B1 116.1(4) . 4 ? C10 O1 B1 114.2(3) . . ? C12 O2 B1 118.9(3) . . ? C2 C1 N1 122.3(4) . . ? C1 C2 C3 120.6(4) . . ? C2 C3 C8 116.3(4) . . ? C2 C3 C4 122.8(4) . . ? C8 C3 C4 120.9(4) . . ? C5 C4 C3 115.9(4) . . ? C5 C4 B1 120.3(4) . . ? C3 C4 B1 123.8(4) . . ? C4 C5 C6 124.0(4) . . ? C7 C6 C5 120.1(4) . . ? C6 C7 C8 119.3(4) . . ? C9 C8 C3 119.0(4) . . ? C9 C8 C7 121.1(4) . . ? C3 C8 C7 119.9(4) . . ? N1 C9 C8 122.9(4) . . ? O1 C10 C11 109.6(4) . . ? C10 C11 C10 110.8(5) 2 . ? C10 C11 C12 107.6(2) 2 2 ? C10 C11 C12 109.1(2) . 2 ? C10 C11 C12 109.1(2) 2 . ? C10 C11 C12 107.6(2) . . ? C12 C11 C12 112.7(5) 2 . ? O2 C12 C11 113.2(3) . . ? 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 O2 B1 O1 C10 41.1(5) . . . . ? C4 B1 O1 C10 171.8(3) . . . . ? N1 B1 O1 C10 -76.5(4) 4_545 . . . ? O1 B1 O2 C12 -30.3(6) . . . . ? C4 B1 O2 C12 -160.0(3) . . . . ? N1 B1 O2 C12 84.7(4) 4_545 . . . ? C9 N1 C1 C2 0.4(6) . . . . ? B1 N1 C1 C2 174.6(4) 4 . . . ? N1 C1 C2 C3 -2.6(7) . . . . ? C1 C2 C3 C8 3.8(6) . . . . ? C1 C2 C3 C4 -177.5(4) . . . . ? C2 C3 C4 C5 -178.4(4) . . . . ? C8 C3 C4 C5 0.3(6) . . . . ? C2 C3 C4 B1 2.9(6) . . . . ? C8 C3 C4 B1 -178.4(4) . . . . ? O2 B1 C4 C5 131.0(4) . . . . ? O1 B1 C4 C5 -2.2(6) . . . . ? N1 B1 C4 C5 -112.3(4) 4_545 . . . ? O2 B1 C4 C3 -50.4(6) . . . . ? O1 B1 C4 C3 176.4(4) . . . . ? N1 B1 C4 C3 66.3(5) 4_545 . . . ? C3 C4 C5 C6 0.3(7) . . . . ? B1 C4 C5 C6 179.1(4) . . . . ? C4 C5 C6 C7 -0.7(7) . . . . ? C5 C6 C7 C8 0.5(7) . . . . ? C2 C3 C8 C9 -2.9(6) . . . . ? C4 C3 C8 C9 178.3(4) . . . . ? C2 C3 C8 C7 178.3(4) . . . . ? C4 C3 C8 C7 -0.4(6) . . . . ? C6 C7 C8 C9 -178.7(4) . . . . ? C6 C7 C8 C3 0.0(7) . . . . ? C1 N1 C9 C8 0.5(6) . . . . ? B1 N1 C9 C8 -173.2(4) 4 . . . ? C3 C8 C9 N1 0.8(6) . . . . ? C7 C8 C9 N1 179.6(4) . . . . ? B1 O1 C10 C11 -57.1(4) . . . . ? O1 C10 C11 C10 179.9(4) . . . 2 ? O1 C10 C11 C12 -61.9(4) . . . 2 ? O1 C10 C11 C12 60.7(4) . . . . ? B1 O2 C12 C11 36.0(5) . . . . ? C10 C11 C12 O2 -170.3(3) 2 . . . ? C10 C11 C12 O2 -50.0(5) . . . . ? C12 C11 C12 O2 70.3(3) 2 . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.337 _refine_diff_density_min -0.347 _refine_diff_density_rms 0.078 data_j4crdrem _database_code_depnum_ccdc_archive 'CCDC 861083' #TrackingRef '- Compound 1 (861083).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H20 B2 N2 O4, C2 H6 O' _chemical_formula_sum 'C25 H26 B2 N2 O5' _chemical_formula_weight 456.10 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' O O 0.0106 0.0060 '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/c 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 19.946(3) _cell_length_b 9.9565(15) _cell_length_c 13.585(2) _cell_angle_alpha 90.00 _cell_angle_beta 127.486(2) _cell_angle_gamma 90.00 _cell_volume 2140.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2398 _cell_measurement_theta_min 2.42 _cell_measurement_theta_max 27.23 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.892 _exptl_absorpt_correction_T_max 0.980 _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 9999 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.42 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1885 _reflns_number_gt 1651 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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. The EtOH solvent molecules in the crystal structure are disordered over two sites with an occupancy of 0.50. DFIX, SIMU, DELU and ISOR instructions have been used during the refinement in order to model the EtOH geometry and thermal motion. ; _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^)+(0.0742P)^2^+4.6708P] 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 1885 _refine_ls_number_parameters 171 _refine_ls_number_restraints 36 _refine_ls_R_factor_all 0.0741 _refine_ls_R_factor_gt 0.0655 _refine_ls_wR_factor_ref 0.1663 _refine_ls_wR_factor_gt 0.1611 _refine_ls_goodness_of_fit_ref 1.172 _refine_ls_restrained_S_all 1.169 _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 B1 B 0.15824(19) 0.4306(3) 0.3123(3) 0.0169(7) Uani 1 1 d . . . N1 N 0.31166(13) 0.8274(2) 0.25475(19) 0.0157(5) Uani 1 1 d . . . O1 O 0.15254(10) 0.34005(18) 0.38963(16) 0.0156(5) Uani 1 1 d . . . O2 O 0.08176(11) 0.49743(17) 0.21535(16) 0.0169(5) Uani 1 1 d . . . C1 C 0.24376(16) 0.7457(3) 0.1761(2) 0.0164(6) Uani 1 1 d . . . H1 H 0.2147 0.7538 0.0892 0.020 Uiso 1 1 calc R . . C2 C 0.21666(16) 0.6530(3) 0.2187(2) 0.0177(6) Uani 1 1 d . . . H2 H 0.1686 0.5994 0.1611 0.021 Uiso 1 1 calc R . . C3 C 0.25895(16) 0.6352(3) 0.3475(2) 0.0161(6) Uani 1 1 d . . . C4 C 0.23583(16) 0.5353(3) 0.3977(2) 0.0161(6) Uani 1 1 d . . . C5 C 0.28361(17) 0.5307(3) 0.5252(2) 0.0202(6) Uani 1 1 d . . . H5 H 0.2702 0.4646 0.5611 0.024 Uiso 1 1 calc R . . C6 C 0.35111(19) 0.6184(3) 0.6047(3) 0.0245(7) Uani 1 1 d . . . H6 H 0.3811 0.6114 0.6919 0.029 Uiso 1 1 calc R . . C7 C 0.37401(18) 0.7132(3) 0.5583(3) 0.0232(7) Uani 1 1 d . . . H7 H 0.4198 0.7722 0.6124 0.028 Uiso 1 1 calc R . . C8 C 0.32868(16) 0.7231(3) 0.4281(2) 0.0171(6) Uani 1 1 d . . . C9 C 0.35137(17) 0.8167(3) 0.3751(2) 0.0171(6) Uani 1 1 d . . . H9 H 0.3977 0.8750 0.4289 0.021 Uiso 1 1 calc R . . C10 C 0.07941(16) 0.2573(3) 0.3233(2) 0.0173(6) Uani 1 1 d . . . H10A H 0.0787 0.1998 0.3821 0.021 Uiso 1 1 calc R . . H10B H 0.0806 0.1982 0.2658 0.021 Uiso 1 1 calc R . . C11 C 0.0000 0.3445(4) 0.2500 0.0155(8) Uani 1 2 d S . . C12 C 0.00353(16) 0.4296(3) 0.1591(2) 0.0171(6) Uani 1 1 d . . . H12A H -0.0068 0.3706 0.0925 0.021 Uiso 1 1 calc R . . H12B H -0.0425 0.4969 0.1202 0.021 Uiso 1 1 calc R . . O31 O 0.0336(4) 0.8171(7) 0.0668(7) 0.0759(18) Uani 0.50 1 d PDU A -1 H31 H 0.069(6) 0.767(10) 0.126(7) 0.114 Uiso 0.50 1 d PD B -1 C31 C 0.0552(9) 0.9548(12) 0.0617(18) 0.080(4) Uani 0.50 1 d PDU A -1 H31A H 0.0934 0.9575 0.0381 0.096 Uiso 0.50 1 calc PR A -1 H31B H 0.0836 0.9989 0.1433 0.096 Uiso 0.50 1 calc PR A -1 C32 C -0.0281(7) 1.0252(13) -0.0361(15) 0.065(3) Uani 0.50 1 d PDU A -1 H32A H -0.0637 0.9656 -0.1076 0.098 Uiso 0.50 1 calc PR A -1 H32B H -0.0167 1.1078 -0.0628 0.098 Uiso 0.50 1 calc PR A -1 H32C H -0.0573 1.0473 -0.0007 0.098 Uiso 0.50 1 calc PR A -1 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 0.0193(15) 0.0166(15) 0.0200(15) 0.0015(12) 0.0146(13) 0.0022(12) N1 0.0166(11) 0.0142(11) 0.0190(12) -0.0006(9) 0.0122(10) 0.0010(9) O1 0.0143(9) 0.0164(9) 0.0185(10) 0.0019(7) 0.0113(8) -0.0003(7) O2 0.0153(10) 0.0165(10) 0.0209(10) 0.0025(8) 0.0120(8) 0.0003(7) C1 0.0153(13) 0.0173(13) 0.0166(13) -0.0005(10) 0.0097(11) 0.0013(10) C2 0.0156(13) 0.0167(14) 0.0194(14) -0.0013(11) 0.0100(12) -0.0006(10) C3 0.0178(13) 0.0138(13) 0.0214(14) 0.0000(11) 0.0143(12) 0.0046(10) C4 0.0178(13) 0.0147(13) 0.0212(14) 0.0026(11) 0.0146(12) 0.0049(10) C5 0.0298(15) 0.0169(14) 0.0241(15) 0.0026(11) 0.0215(13) 0.0012(12) C6 0.0348(17) 0.0241(15) 0.0171(14) -0.0009(12) 0.0170(13) -0.0022(12) C7 0.0277(16) 0.0216(15) 0.0176(14) -0.0045(12) 0.0125(13) -0.0036(12) C8 0.0186(14) 0.0149(13) 0.0208(14) -0.0014(11) 0.0137(12) 0.0017(11) C9 0.0184(13) 0.0162(14) 0.0195(14) -0.0038(11) 0.0130(12) -0.0012(10) C10 0.0202(14) 0.0169(14) 0.0181(13) 0.0027(11) 0.0133(12) 0.0000(11) C11 0.0157(18) 0.0178(19) 0.0154(18) 0.000 0.0108(16) 0.000 C12 0.0134(13) 0.0202(14) 0.0181(14) 0.0019(11) 0.0098(11) 0.0017(10) O31 0.061(4) 0.072(4) 0.086(4) -0.011(3) 0.040(3) 0.006(3) C31 0.076(8) 0.083(5) 0.081(7) -0.003(5) 0.047(6) -0.001(5) C32 0.050(7) 0.064(5) 0.067(7) -0.015(4) 0.027(5) -0.020(5) _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 O2 1.435(3) . ? B1 O1 1.440(3) . ? B1 C4 1.625(4) . ? B1 N1 1.707(4) 4_545 ? N1 C9 1.317(3) . ? N1 C1 1.370(3) . ? N1 B1 1.707(4) 4 ? O1 C10 1.421(3) . ? O2 C12 1.423(3) . ? C1 C2 1.364(4) . ? C2 C3 1.417(4) . ? C3 C8 1.430(4) . ? C3 C4 1.431(4) . ? C4 C5 1.378(4) . ? C5 C6 1.404(4) . ? C6 C7 1.360(4) . ? C7 C8 1.417(4) . ? C8 C9 1.410(4) . ? C10 C11 1.528(3) . ? C11 C10 1.528(3) 2 ? C11 C12 1.534(3) 2 ? C11 C12 1.534(3) . ? O31 C31 1.452(9) . ? C31 C32 1.526(8) . ? 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 O2 B1 O1 116.6(2) . . ? O2 B1 C4 112.1(2) . . ? O1 B1 C4 110.2(2) . . ? O2 B1 N1 108.2(2) . 4_545 ? O1 B1 N1 102.8(2) . 4_545 ? C4 B1 N1 105.99(19) . 4_545 ? C9 N1 C1 118.9(2) . . ? C9 N1 B1 124.7(2) . 4 ? C1 N1 B1 116.3(2) . 4 ? C10 O1 B1 114.00(19) . . ? C12 O2 B1 118.6(2) . . ? C2 C1 N1 122.0(2) . . ? C1 C2 C3 121.1(2) . . ? C2 C3 C8 116.1(2) . . ? C2 C3 C4 123.6(2) . . ? C8 C3 C4 120.4(2) . . ? C5 C4 C3 116.4(2) . . ? C5 C4 B1 120.3(2) . . ? C3 C4 B1 123.3(2) . . ? C4 C5 C6 123.5(3) . . ? C7 C6 C5 120.7(3) . . ? C6 C7 C8 119.2(3) . . ? C9 C8 C7 121.6(2) . . ? C9 C8 C3 118.6(2) . . ? C7 C8 C3 119.8(2) . . ? N1 C9 C8 123.4(2) . . ? O1 C10 C11 109.9(2) . . ? C10 C11 C10 110.7(3) 2 . ? C10 C11 C12 107.53(13) 2 2 ? C10 C11 C12 109.05(14) . 2 ? C10 C11 C12 109.05(14) 2 . ? C10 C11 C12 107.53(13) . . ? C12 C11 C12 113.0(3) 2 . ? O2 C12 C11 113.76(18) . . ? O31 C31 C32 106.1(9) . . ? 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 O2 B1 O1 C10 42.4(3) . . . . ? C4 B1 O1 C10 171.63(19) . . . . ? N1 B1 O1 C10 -75.8(2) 4_545 . . . ? O1 B1 O2 C12 -31.7(3) . . . . ? C4 B1 O2 C12 -160.0(2) . . . . ? N1 B1 O2 C12 83.5(2) 4_545 . . . ? C9 N1 C1 C2 -0.6(4) . . . . ? B1 N1 C1 C2 176.0(2) 4 . . . ? N1 C1 C2 C3 -1.3(4) . . . . ? C1 C2 C3 C8 2.3(4) . . . . ? C1 C2 C3 C4 -176.9(2) . . . . ? C2 C3 C4 C5 179.7(2) . . . . ? C8 C3 C4 C5 0.5(4) . . . . ? C2 C3 C4 B1 0.0(4) . . . . ? C8 C3 C4 B1 -179.2(2) . . . . ? O2 B1 C4 C5 130.1(2) . . . . ? O1 B1 C4 C5 -1.6(3) . . . . ? N1 B1 C4 C5 -112.1(2) 4_545 . . . ? O2 B1 C4 C3 -50.3(3) . . . . ? O1 B1 C4 C3 178.1(2) . . . . ? N1 B1 C4 C3 67.5(3) 4_545 . . . ? C3 C4 C5 C6 0.8(4) . . . . ? B1 C4 C5 C6 -179.5(2) . . . . ? C4 C5 C6 C7 -1.2(4) . . . . ? C5 C6 C7 C8 0.2(4) . . . . ? C6 C7 C8 C9 -178.0(3) . . . . ? C6 C7 C8 C3 1.0(4) . . . . ? C2 C3 C8 C9 -1.7(3) . . . . ? C4 C3 C8 C9 177.6(2) . . . . ? C2 C3 C8 C7 179.3(2) . . . . ? C4 C3 C8 C7 -1.4(4) . . . . ? C1 N1 C9 C8 1.3(4) . . . . ? B1 N1 C9 C8 -175.0(2) 4 . . . ? C7 C8 C9 N1 178.9(2) . . . . ? C3 C8 C9 N1 -0.1(4) . . . . ? B1 O1 C10 C11 -57.7(2) . . . . ? O1 C10 C11 C10 179.3(2) . . . 2 ? O1 C10 C11 C12 -62.5(2) . . . 2 ? O1 C10 C11 C12 60.3(2) . . . . ? B1 O2 C12 C11 36.8(3) . . . . ? C10 C11 C12 O2 -169.8(2) 2 . . . ? C10 C11 C12 O2 -49.7(3) . . . . ? C12 C11 C12 O2 70.68(18) 2 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.347 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.073 # Attachment '- Compound 2 (861084).cif' data_j4crachm _database_code_depnum_ccdc_archive 'CCDC 861084' #TrackingRef '- Compound 2 (861084).cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H16 B2 N2 O4, 4(C2 H6 O),H2 O, C7 H8' _chemical_formula_sum 'C30 H50 B2 N2 O9' _chemical_formula_weight 604.34 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M P4(3)2(1)2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-y+1/2, x+1/2, z+3/4' 'y+1/2, -x+1/2, z+1/4' '-x+1/2, y+1/2, -z+3/4' 'x+1/2, -y+1/2, -z+1/4' 'y, x, -z' '-y, -x, -z+1/2' _cell_length_a 9.4861(11) _cell_length_b 9.4861(11) _cell_length_c 36.031(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3242.3(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 6787 _cell_measurement_theta_min 2.24 _cell_measurement_theta_max 24.66 _exptl_crystal_description 'rectangular prism' _exptl_crystal_colour yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.238 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.97 _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 30879 _diffrn_reflns_av_R_equivalents 0.0744 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2853 _reflns_number_gt 2250 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _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. Although relatively large crystals could be grown for this compound, they diffracted only weakly. This can be attributed to the presence of large amounts of disordered solvent in the crystal lattice: 64 percent of the total unit cell volume. The electron density was too diffuse to be meaningfully modeled and its scattering contributions were removed using the SQUEEZE routine in PLATON. The low resolution of the data affects the reliability of the bond lengths and angles, and the refinement of the anisotropic thermal parameters. ; _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^)+(0.1310P)^2^+0.0986P] 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 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 2853 _refine_ls_number_parameters 105 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0907 _refine_ls_R_factor_gt 0.0722 _refine_ls_wR_factor_ref 0.2083 _refine_ls_wR_factor_gt 0.1993 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 -0.115 -0.052 -0.003 2070 787 ' ' _platon_squeeze_details ; The unit cell contains 16 EtOH, 4 H2O and 4 toluene molecules which have been treated as a diffuse contribution to the overall scattering without specific atom positions by SQUEEZE/PLATON ; loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group B1 B 0.3352(4) 0.3072(3) 0.07449(9) 0.0375(8) Uani 1 1 d . . . N1 N -0.0221(3) 0.2214(2) 0.15116(6) 0.0382(7) Uani 1 1 d . . . O1 O 0.3321(2) 0.2083(2) 0.04469(5) 0.0394(6) Uani 1 1 d . . . O2 O 0.3388(2) 0.4556(2) 0.06420(5) 0.0437(6) Uani 1 1 d . . . C1 C 0.0370(3) 0.1203(3) 0.13029(7) 0.0387(8) Uani 1 1 d . . . H1 H 0.0000 0.0274 0.1320 0.046 Uiso 1 1 calc R . . C2 C 0.1482(3) 0.1436(3) 0.10664(8) 0.0434(8) Uani 1 1 d . . . H2 H 0.1865 0.0676 0.0928 0.052 Uiso 1 1 calc R . . C3 C 0.2042(3) 0.2767(3) 0.10301(7) 0.0348(7) Uani 1 1 d . . . C4 C 0.1444(4) 0.3829(3) 0.12507(8) 0.0460(8) Uani 1 1 d . . . H4 H 0.1800 0.4763 0.1236 0.055 Uiso 1 1 calc R . . C5 C 0.0357(4) 0.3536(3) 0.14855(8) 0.0467(8) Uani 1 1 d . . . H5 H -0.0012 0.4271 0.1636 0.056 Uiso 1 1 calc R . . C6 C 0.4121(4) 0.2431(3) 0.01327(8) 0.0441(8) Uani 1 1 d . . . H6A H 0.3872 0.1776 -0.0071 0.053 Uiso 1 1 calc R . . H6B H 0.5131 0.2290 0.0191 0.053 Uiso 1 1 calc R . . C7 C 0.3914(3) 0.3914(3) 0.0000 0.0342(10) Uani 1 2 d S . . C8 C 0.4226(3) 0.4903(3) 0.03273(7) 0.0403(8) Uani 1 1 d . . . H8A H 0.5236 0.4832 0.0394 0.048 Uiso 1 1 calc R . . H8B H 0.4033 0.5888 0.0252 0.048 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 B1 0.046(2) 0.0315(18) 0.0353(18) -0.0030(14) -0.0015(16) 0.0007(16) N1 0.0605(17) 0.0229(12) 0.0313(12) -0.0034(10) -0.0090(12) 0.0066(12) O1 0.0557(13) 0.0395(12) 0.0228(10) -0.0026(9) -0.0002(9) -0.0016(10) O2 0.0683(15) 0.0340(11) 0.0289(10) 0.0064(9) 0.0033(10) -0.0041(10) C1 0.067(2) 0.0180(14) 0.0316(14) -0.0041(12) 0.0120(15) 0.0030(13) C2 0.0558(19) 0.0366(17) 0.0377(16) -0.0146(14) 0.0057(14) -0.0016(14) C3 0.055(2) 0.0289(15) 0.0203(13) 0.0031(12) -0.0061(13) 0.0044(13) C4 0.070(2) 0.0315(17) 0.0363(16) -0.0048(13) 0.0075(16) -0.0022(15) C5 0.072(2) 0.0276(17) 0.0408(17) -0.0112(14) 0.0116(17) -0.0002(15) C6 0.053(2) 0.051(2) 0.0277(15) 0.0032(13) -0.0062(14) 0.0082(16) C7 0.0366(15) 0.0366(15) 0.0294(19) -0.0026(13) 0.0026(13) -0.0119(18) C8 0.0503(19) 0.0350(17) 0.0355(16) 0.0113(13) -0.0101(13) 0.0012(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag B1 O1 1.426(4) . ? B1 O2 1.456(4) . ? B1 N1 1.636(4) 6 ? B1 C3 1.638(5) . ? N1 C1 1.342(3) . ? N1 C5 1.372(4) . ? O1 C6 1.402(3) . ? O2 C8 1.424(3) . ? C1 C2 1.374(4) . ? C2 C3 1.376(4) . ? C3 C4 1.404(4) . ? C4 C5 1.362(4) . ? C6 C7 1.498(4) . ? C7 C6 1.498(4) 7 ? C7 C8 1.536(3) . ? C7 C8 1.536(3) 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 _geom_angle_publ_flag O1 B1 O2 116.4(2) . . ? O1 B1 N1 108.1(2) . 6 ? O2 B1 N1 106.1(2) . 6 ? O1 B1 C3 109.9(2) . . ? O2 B1 C3 110.4(2) . . ? N1 B1 C3 105.2(2) 6 . ? C1 N1 C5 116.7(3) . . ? C1 N1 B1 121.8(2) . 6_455 ? C5 N1 B1 121.3(2) . 6_455 ? C6 O1 B1 116.3(2) . . ? C8 O2 B1 116.1(2) . . ? N1 C1 C2 123.5(3) . . ? C1 C2 C3 120.3(3) . . ? C2 C3 C4 116.6(3) . . ? C2 C3 B1 121.0(3) . . ? C4 C3 B1 122.4(3) . . ? C5 C4 C3 120.8(3) . . ? C4 C5 N1 122.1(3) . . ? O1 C6 C7 114.0(2) . . ? C6 C7 C6 110.4(3) . 7 ? C6 C7 C8 107.64(15) . . ? C6 C7 C8 110.24(16) 7 . ? C8 C7 C8 110.7(3) . 7 ? O2 C8 C7 111.3(2) . . ? 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 O2 B1 O1 C6 36.9(4) . . . . ? N1 B1 O1 C6 -82.3(3) 6 . . . ? C3 B1 O1 C6 163.3(2) . . . . ? O1 B1 O2 C8 -38.3(4) . . . . ? N1 B1 O2 C8 82.1(3) 6 . . . ? C3 B1 O2 C8 -164.4(2) . . . . ? C5 N1 C1 C2 -1.1(4) . . . . ? B1 N1 C1 C2 173.3(3) 6_455 . . . ? N1 C1 C2 C3 -0.8(5) . . . . ? C1 C2 C3 C4 1.5(4) . . . . ? C1 C2 C3 B1 -179.1(3) . . . . ? O1 B1 C3 C2 27.5(4) . . . . ? O2 B1 C3 C2 157.2(3) . . . . ? N1 B1 C3 C2 -88.7(3) 6 . . . ? O1 B1 C3 C4 -153.1(3) . . . . ? O2 B1 C3 C4 -23.4(4) . . . . ? N1 B1 C3 C4 90.7(3) 6 . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? B1 C3 C4 C5 -179.8(3) . . . . ? C3 C4 C5 N1 -1.5(5) . . . . ? C1 N1 C5 C4 2.3(4) . . . . ? B1 N1 C5 C4 -172.2(3) 6_455 . . . ? B1 O1 C6 C7 -47.4(3) . . . . ? O1 C6 C7 C6 -65.0(2) . . . 7 ? O1 C6 C7 C8 55.3(3) . . . . ? O1 C6 C7 C8 176.2(2) . . . 7 ? B1 O2 C8 C7 48.1(3) . . . . ? C6 C7 C8 O2 -55.1(3) . . . . ? C6 C7 C8 O2 65.3(3) 7 . . . ? C8 C7 C8 O2 -175.7(3) 7 . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.282 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.058