# Supplementary data for Dalton Trans. # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Peter Iovine' _publ_contact_author_email PIOVINE@SANDIEGO.EDU _publ_section_title ; Hetero-arylboroxines: The First Rational Synthesis, X-ray Crystallographic and Computational Analysis ; _publ_author_name 'Peter Iovine' data_Iovinecompd3a _database_code_depnum_ccdc_archive 'CCDC 671272' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'JL_15A batch 2' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 B3 F2 N O3' _chemical_formula_weight 404.81 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca 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 11.5420(10) _cell_length_b 18.9350(15) _cell_length_c 19.6870(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4302.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4218 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 21.11 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1680 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9819 _exptl_absorpt_correction_T_max 0.9819 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 0.3 _diffrn_refln_scan_rate 5 _space_group.centring_type primitive _space_group.IT_number 61 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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_reflns_number 23336 _diffrn_reflns_av_R_equivalents 0.0450 _diffrn_reflns_av_sigmaI/netI 0.0296 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3806 _reflns_number_gt 2885 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2004 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.0525P)^2^+1.0031P] 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 3806 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0697 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1281 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C1 C 0.22548(18) 0.17480(10) 0.39130(10) 0.0603(5) Uani 1 1 d . . . C2 C 0.2674(2) 0.11977(13) 0.35161(13) 0.0872(7) Uani 1 1 d . . . H2 H 0.2298 0.0764 0.3520 0.105 Uiso 1 1 calc R . . C3 C 0.3645(3) 0.12896(18) 0.31164(16) 0.1128(10) Uani 1 1 d . . . H3 H 0.3912 0.0917 0.2851 0.135 Uiso 1 1 calc R . . C4 C 0.4220(3) 0.1922(2) 0.31062(15) 0.1080(10) Uani 1 1 d . . . H4 H 0.4879 0.1973 0.2839 0.130 Uiso 1 1 calc R . . C5 C 0.3828(2) 0.24820(15) 0.34893(13) 0.0823(7) Uani 1 1 d . . . H5 H 0.4213 0.2913 0.3483 0.099 Uiso 1 1 calc R . . C6 C 0.28431(18) 0.23869(11) 0.38857(10) 0.0617(5) Uani 1 1 d . . . C7 C 0.2280(2) 0.29308(11) 0.43251(11) 0.0713(6) Uani 1 1 d . . . H7A H 0.2320 0.3393 0.4115 0.086 Uiso 1 1 calc R . . H7B H 0.2652 0.2952 0.4766 0.086 Uiso 1 1 calc R . . C8 C 0.0480(3) 0.30142(14) 0.49895(14) 0.1039(9) Uani 1 1 d . . . H8A H 0.0492 0.3519 0.4946 0.156 Uiso 1 1 calc R . . H8B H 0.0888 0.2879 0.5394 0.156 Uiso 1 1 calc R . . H8C H -0.0308 0.2854 0.5017 0.156 Uiso 1 1 calc R . . C9 C 0.0396(2) 0.28849(13) 0.37637(13) 0.0855(7) Uani 1 1 d . . . H9A H -0.0364 0.2679 0.3780 0.128 Uiso 1 1 calc R . . H9B H 0.0802 0.2710 0.3373 0.128 Uiso 1 1 calc R . . H9C H 0.0330 0.3389 0.3735 0.128 Uiso 1 1 calc R . . C10 C -0.16805(17) 0.07377(10) 0.44682(10) 0.0547(5) Uani 1 1 d . . . C11 C -0.21780(18) 0.08695(11) 0.38410(11) 0.0658(6) Uani 1 1 d . . . H11 H -0.1805 0.1170 0.3538 0.079 Uiso 1 1 calc R . . C12 C -0.3219(2) 0.05627(13) 0.36556(13) 0.0762(6) Uani 1 1 d . . . H12 H -0.3549 0.0655 0.3234 0.091 Uiso 1 1 calc R . . C13 C -0.37480(19) 0.01240(12) 0.41034(13) 0.0721(6) Uani 1 1 d . . . C14 C -0.33059(18) -0.00262(11) 0.47234(13) 0.0709(6) Uani 1 1 d . . . H14 H -0.3690 -0.0330 0.5019 0.085 Uiso 1 1 calc R . . C15 C -0.22667(18) 0.02852(10) 0.49058(11) 0.0607(5) Uani 1 1 d . . . H15 H -0.1953 0.0190 0.5331 0.073 Uiso 1 1 calc R . . C16 C 0.13143(17) 0.11236(10) 0.62935(10) 0.0540(5) Uani 1 1 d . . . C17 C 0.2358(2) 0.13872(13) 0.65318(11) 0.0746(6) Uani 1 1 d . . . H17 H 0.2809 0.1663 0.6244 0.090 Uiso 1 1 calc R . . C18 C 0.2749(2) 0.12548(14) 0.71794(13) 0.0858(7) Uani 1 1 d . . . H18 H 0.3455 0.1434 0.7328 0.103 Uiso 1 1 calc R . . C19 C 0.2084(2) 0.08591(13) 0.75939(11) 0.0738(6) Uani 1 1 d . . . C20 C 0.1043(2) 0.05965(12) 0.73977(12) 0.0760(6) Uani 1 1 d . . . H20 H 0.0591 0.0336 0.7698 0.091 Uiso 1 1 calc R . . C21 C 0.06683(19) 0.07244(11) 0.67429(11) 0.0647(5) Uani 1 1 d . . . H21 H -0.0036 0.0537 0.6601 0.078 Uiso 1 1 calc R . . B1 B 0.1201(2) 0.18023(12) 0.44310(12) 0.0584(6) Uani 1 1 d . . . B2 B -0.0502(2) 0.10760(11) 0.46853(12) 0.0548(5) Uani 1 1 d . . . B3 B 0.09114(19) 0.12562(12) 0.55503(12) 0.0548(5) Uani 1 1 d . . . N1 N 0.10477(15) 0.26917(8) 0.43914(9) 0.0647(5) Uani 1 1 d . . . O1 O 0.01071(12) 0.14837(7) 0.42503(7) 0.0670(4) Uani 1 1 d . . . O2 O -0.01138(11) 0.09593(7) 0.53351(7) 0.0623(4) Uani 1 1 d . . . O3 O 0.15443(12) 0.16605(7) 0.51272(7) 0.0645(4) Uani 1 1 d . . . F1 F -0.47652(12) -0.01872(9) 0.39162(8) 0.1080(5) Uani 1 1 d . . . F2 F 0.24729(16) 0.07085(9) 0.82296(7) 0.1103(6) 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 C1 0.0681(13) 0.0551(11) 0.0578(12) 0.0065(9) -0.0071(10) 0.0011(10) C2 0.112(2) 0.0655(14) 0.0844(17) 0.0029(13) 0.0082(16) 0.0116(14) C3 0.134(3) 0.101(2) 0.103(2) 0.0091(18) 0.036(2) 0.040(2) C4 0.091(2) 0.134(3) 0.099(2) 0.032(2) 0.0304(16) 0.032(2) C5 0.0671(15) 0.0965(17) 0.0833(17) 0.0258(15) -0.0021(13) -0.0094(14) C6 0.0613(12) 0.0662(13) 0.0576(12) 0.0095(10) -0.0064(10) -0.0057(10) C7 0.0826(16) 0.0598(12) 0.0716(14) 0.0033(11) -0.0020(12) -0.0213(11) C8 0.130(2) 0.0770(16) 0.105(2) -0.0162(15) 0.0408(18) 0.0009(16) C9 0.0778(16) 0.0728(15) 0.1059(19) 0.0232(14) -0.0049(14) 0.0113(12) C10 0.0564(11) 0.0477(10) 0.0599(12) -0.0092(9) -0.0009(9) 0.0009(9) C11 0.0641(13) 0.0667(13) 0.0667(14) -0.0028(10) -0.0052(11) -0.0042(10) C12 0.0704(15) 0.0840(15) 0.0742(15) -0.0119(13) -0.0199(12) 0.0003(13) C13 0.0561(13) 0.0747(14) 0.0855(17) -0.0219(13) -0.0082(12) -0.0103(11) C14 0.0645(13) 0.0643(13) 0.0840(16) -0.0107(12) 0.0052(12) -0.0152(11) C15 0.0623(13) 0.0557(11) 0.0640(13) -0.0071(10) -0.0023(10) -0.0043(10) C16 0.0538(11) 0.0531(10) 0.0550(11) -0.0027(9) 0.0025(9) -0.0007(9) C17 0.0741(15) 0.0899(16) 0.0597(13) 0.0055(12) -0.0043(11) -0.0201(12) C18 0.0858(17) 0.1041(19) 0.0674(15) -0.0033(14) -0.0182(13) -0.0185(15) C19 0.0969(18) 0.0763(15) 0.0484(13) -0.0078(11) -0.0070(12) 0.0168(14) C20 0.0929(18) 0.0733(14) 0.0618(14) 0.0086(11) 0.0151(12) 0.0072(13) C21 0.0644(13) 0.0660(12) 0.0637(13) 0.0038(10) 0.0035(10) -0.0024(10) B1 0.0643(14) 0.0528(13) 0.0581(14) 0.0048(10) -0.0083(11) -0.0103(11) B2 0.0598(14) 0.0470(12) 0.0574(14) -0.0033(10) -0.0021(11) -0.0002(10) B3 0.0531(13) 0.0505(12) 0.0608(14) -0.0022(10) 0.0017(11) -0.0039(10) N1 0.0727(12) 0.0519(10) 0.0695(11) 0.0011(8) 0.0065(9) -0.0027(8) O1 0.0709(9) 0.0691(9) 0.0609(9) 0.0075(7) -0.0118(7) -0.0191(7) O2 0.0587(8) 0.0672(9) 0.0609(8) 0.0055(7) -0.0045(7) -0.0143(7) O3 0.0657(9) 0.0690(9) 0.0588(9) 0.0082(7) -0.0080(7) -0.0190(7) F1 0.0733(9) 0.1260(13) 0.1247(13) -0.0244(10) -0.0203(8) -0.0326(9) F2 0.1531(15) 0.1219(12) 0.0558(8) 0.0019(8) -0.0213(9) 0.0162(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 C1 C6 1.388(3) . ? C1 C2 1.390(3) . ? C1 B1 1.590(3) . ? C2 C3 1.380(4) . ? C2 H2 0.9300 . ? C3 C4 1.368(4) . ? C3 H3 0.9300 . ? C4 C5 1.378(4) . ? C4 H4 0.9300 . ? C5 C6 1.391(3) . ? C5 H5 0.9300 . ? C6 C7 1.494(3) . ? C7 N1 1.498(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N1 1.479(3) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 N1 1.492(3) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.384(3) . ? C10 C15 1.391(3) . ? C10 B2 1.563(3) . ? C11 C12 1.384(3) . ? C11 H11 0.9300 . ? C12 C13 1.356(3) . ? C12 H12 0.9300 . ? C13 C14 1.353(3) . ? C13 F1 1.364(2) . ? C14 C15 1.384(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 C21 1.382(3) . ? C16 C17 1.386(3) . ? C16 B3 1.556(3) . ? C17 C18 1.376(3) . ? C17 H17 0.9300 . ? C18 C19 1.348(3) . ? C18 H18 0.9300 . ? C19 C20 1.356(3) . ? C19 F2 1.360(2) . ? C20 C21 1.381(3) . ? C20 H20 0.9300 . ? C21 H21 0.9300 . ? B1 O1 1.444(3) . ? B1 O3 1.452(3) . ? B1 N1 1.695(3) . ? B2 O1 1.350(3) . ? B2 O2 1.373(3) . ? B3 O3 1.347(3) . ? B3 O2 1.377(3) . ? 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 C6 C1 C2 117.5(2) . . ? C6 C1 B1 110.03(18) . . ? C2 C1 B1 132.5(2) . . ? C3 C2 C1 120.6(3) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.4(3) . . ? C3 C4 H4 119.8 . . ? C5 C4 H4 119.8 . . ? C4 C5 C6 118.4(3) . . ? C4 C5 H5 120.8 . . ? C6 C5 H5 120.8 . . ? C1 C6 C5 122.3(2) . . ? C1 C6 C7 111.44(18) . . ? C5 C6 C7 126.3(2) . . ? C6 C7 N1 104.78(16) . . ? C6 C7 H7A 110.8 . . ? N1 C7 H7A 110.8 . . ? C6 C7 H7B 110.8 . . ? N1 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C15 117.50(19) . . ? C11 C10 B2 122.06(19) . . ? C15 C10 B2 120.44(18) . . ? C12 C11 C10 121.3(2) . . ? C12 C11 H11 119.3 . . ? C10 C11 H11 119.3 . . ? C13 C12 C11 118.4(2) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C14 C13 C12 123.1(2) . . ? C14 C13 F1 118.5(2) . . ? C12 C13 F1 118.4(2) . . ? C13 C14 C15 118.1(2) . . ? C13 C14 H14 120.9 . . ? C15 C14 H14 120.9 . . ? C14 C15 C10 121.6(2) . . ? C14 C15 H15 119.2 . . ? C10 C15 H15 119.2 . . ? C21 C16 C17 116.69(19) . . ? C21 C16 B3 121.95(18) . . ? C17 C16 B3 121.34(18) . . ? C18 C17 C16 122.2(2) . . ? C18 C17 H17 118.9 . . ? C16 C17 H17 118.9 . . ? C19 C18 C17 118.4(2) . . ? C19 C18 H18 120.8 . . ? C17 C18 H18 120.8 . . ? C18 C19 C20 122.4(2) . . ? C18 C19 F2 119.0(2) . . ? C20 C19 F2 118.6(2) . . ? C19 C20 C21 118.6(2) . . ? C19 C20 H20 120.7 . . ? C21 C20 H20 120.7 . . ? C20 C21 C16 121.6(2) . . ? C20 C21 H21 119.2 . . ? C16 C21 H21 119.2 . . ? O1 B1 O3 113.19(17) . . ? O1 B1 C1 118.94(18) . . ? O3 B1 C1 112.63(18) . . ? O1 B1 N1 108.20(17) . . ? O3 B1 N1 104.81(16) . . ? C1 B1 N1 96.58(15) . . ? O1 B2 O2 120.85(18) . . ? O1 B2 C10 120.93(19) . . ? O2 B2 C10 118.20(18) . . ? O3 B3 O2 120.53(19) . . ? O3 B3 C16 120.75(18) . . ? O2 B3 C16 118.71(18) . . ? C8 N1 C9 109.6(2) . . ? C8 N1 C7 111.40(19) . . ? C9 N1 C7 109.40(17) . . ? C8 N1 B1 114.83(17) . . ? C9 N1 B1 109.53(16) . . ? C7 N1 B1 101.83(15) . . ? B2 O1 B1 122.55(17) . . ? B2 O2 B3 120.08(17) . . ? B3 O3 B1 122.76(16) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.133 _refine_diff_density_min -0.155 _refine_diff_density_rms 0.028 data_Iovinecompd3b _database_code_depnum_ccdc_archive 'CCDC 671273' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common SN49B _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 B3 N O5' _chemical_formula_weight 428.88 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.8312(13) _cell_length_b 12.0846(12) _cell_length_c 15.7327(16) _cell_angle_alpha 90.00 _cell_angle_beta 112.252(2) _cell_angle_gamma 90.00 _cell_volume 2257.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3069 _cell_measurement_theta_min 2.19 _cell_measurement_theta_max 26.81 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.262 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9831 _exptl_absorpt_correction_T_max 0.9898 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 0.3 _diffrn_refln_scan_rate 5 _space_group.centring_type primitive _space_group.IT_number 14 _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_reflns_number 9555 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0471 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 28.27 _reflns_number_total 4959 _reflns_number_gt 3455 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2004 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.0799P)^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_number_reflns 4959 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0506 _refine_ls_wR_factor_ref 0.1378 _refine_ls_wR_factor_gt 0.1255 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 C1 C 0.21223(12) 0.02019(12) 0.62322(11) 0.0234(3) Uani 1 1 d . . . C2 C 0.20921(13) 0.02091(13) 0.71022(12) 0.0280(4) Uani 1 1 d . . . H2 H 0.2518 0.0744 0.7538 0.034 Uiso 1 1 calc R . . C3 C 0.14458(14) -0.05572(14) 0.73452(12) 0.0320(4) Uani 1 1 d . . . H3 H 0.1432 -0.0542 0.7945 0.038 Uiso 1 1 calc R . . C4 C 0.08229(15) -0.13416(15) 0.67182(13) 0.0384(4) Uani 1 1 d . . . H4 H 0.0386 -0.1866 0.6889 0.046 Uiso 1 1 calc R . . C5 C 0.08348(15) -0.13632(15) 0.58404(13) 0.0381(4) Uani 1 1 d . . . H5 H 0.0408 -0.1898 0.5406 0.046 Uiso 1 1 calc R . . C6 C 0.14792(13) -0.05911(13) 0.56095(12) 0.0280(4) Uani 1 1 d . . . C7 C 0.15830(14) -0.04931(14) 0.46921(12) 0.0323(4) Uani 1 1 d . . . H7A H 0.1587 -0.1233 0.4423 0.039 Uiso 1 1 calc R . . H7B H 0.0953 -0.0055 0.4259 0.039 Uiso 1 1 calc R . . C8 C 0.36089(15) -0.07453(14) 0.52169(13) 0.0383(5) Uani 1 1 d . . . H8A H 0.3528 -0.1266 0.4718 0.057 Uiso 1 1 calc R . . H8B H 0.3568 -0.1150 0.5743 0.057 Uiso 1 1 calc R . . H8C H 0.4338 -0.0368 0.5400 0.057 Uiso 1 1 calc R . . C9 C 0.27106(16) 0.06503(14) 0.40676(12) 0.0371(4) Uani 1 1 d . . . H9A H 0.3423 0.1051 0.4225 0.056 Uiso 1 1 calc R . . H9B H 0.2082 0.1173 0.3837 0.056 Uiso 1 1 calc R . . H9C H 0.2643 0.0099 0.3593 0.056 Uiso 1 1 calc R . . C10 C 0.57866(12) 0.22153(12) 0.67912(11) 0.0230(3) Uani 1 1 d . . . C11 C 0.64014(13) 0.31272(13) 0.66861(11) 0.0258(4) Uani 1 1 d . . . H11 H 0.6011 0.3715 0.6293 0.031 Uiso 1 1 calc R . . C12 C 0.75490(13) 0.31996(13) 0.71322(11) 0.0280(4) Uani 1 1 d . . . H12 H 0.7943 0.3823 0.7038 0.034 Uiso 1 1 calc R . . C13 C 0.81313(12) 0.23582(13) 0.77219(11) 0.0264(4) Uani 1 1 d . . . C14 C 0.75547(13) 0.14414(13) 0.78502(11) 0.0278(4) Uani 1 1 d . . . H14 H 0.7947 0.0864 0.8254 0.033 Uiso 1 1 calc R . . C15 C 0.63989(13) 0.13810(13) 0.73805(11) 0.0263(4) Uani 1 1 d . . . H15 H 0.6010 0.0747 0.7463 0.032 Uiso 1 1 calc R . . C16 C 0.99068(16) 0.16291(16) 0.86939(16) 0.0527(6) Uani 1 1 d . . . H16A H 0.9680 0.1496 0.9214 0.079 Uiso 1 1 calc R . . H16B H 1.0709 0.1817 0.8923 0.079 Uiso 1 1 calc R . . H16C H 0.9772 0.0960 0.8315 0.079 Uiso 1 1 calc R . . C17 C 0.20570(13) 0.40132(12) 0.49568(11) 0.0228(3) Uani 1 1 d . . . C18 C 0.09162(13) 0.40094(13) 0.44027(11) 0.0252(4) Uani 1 1 d . . . H18 H 0.0527 0.3322 0.4279 0.030 Uiso 1 1 calc R . . C19 C 0.03225(13) 0.49618(13) 0.40239(11) 0.0263(4) Uani 1 1 d . . . H19 H -0.0453 0.4923 0.3639 0.032 Uiso 1 1 calc R . . C20 C 0.08706(13) 0.59696(13) 0.42126(11) 0.0264(4) Uani 1 1 d . . . C21 C 0.20101(14) 0.60079(13) 0.47782(12) 0.0341(4) Uani 1 1 d . . . H21 H 0.2389 0.6699 0.4923 0.041 Uiso 1 1 calc R . . C22 C 0.25843(14) 0.50449(13) 0.51270(12) 0.0303(4) Uani 1 1 d . . . H22 H 0.3365 0.5084 0.5496 0.036 Uiso 1 1 calc R . . C23 C -0.07524(14) 0.69600(14) 0.32383(13) 0.0362(4) Uani 1 1 d . . . H23A H -0.0804 0.6513 0.2704 0.054 Uiso 1 1 calc R . . H23B H -0.0992 0.7719 0.3041 0.054 Uiso 1 1 calc R . . H23C H -0.1241 0.6643 0.3526 0.054 Uiso 1 1 calc R . . B1 B 0.27825(15) 0.09621(14) 0.57698(13) 0.0241(4) Uani 1 1 d . . . B2 B 0.44917(15) 0.21100(14) 0.62783(13) 0.0239(4) Uani 1 1 d . . . B3 B 0.27156(15) 0.29382(14) 0.53721(12) 0.0224(4) Uani 1 1 d . . . N1 N 0.26861(12) 0.00873(11) 0.48964(10) 0.0286(3) Uani 1 1 d . . . O1 O 0.39682(9) 0.11440(9) 0.62954(8) 0.0288(3) Uani 1 1 d . . . O2 O 0.38828(8) 0.30131(8) 0.58028(8) 0.0257(3) Uani 1 1 d . . . O3 O 0.21845(8) 0.19654(8) 0.53403(7) 0.0246(3) Uani 1 1 d . . . O4 O 0.92682(9) 0.25169(10) 0.81578(9) 0.0373(3) Uani 1 1 d . . . O5 O 0.03835(10) 0.69671(9) 0.38839(8) 0.0355(3) 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 C1 0.0212(8) 0.0206(8) 0.0271(9) 0.0010(6) 0.0077(7) 0.0027(6) C2 0.0257(8) 0.0263(9) 0.0285(9) 0.0007(7) 0.0063(7) 0.0041(7) C3 0.0346(9) 0.0369(10) 0.0268(9) 0.0057(8) 0.0143(8) 0.0032(8) C4 0.0391(10) 0.0395(10) 0.0408(11) 0.0052(9) 0.0198(9) -0.0103(8) C5 0.0449(11) 0.0334(10) 0.0376(11) -0.0063(8) 0.0174(9) -0.0162(8) C6 0.0294(9) 0.0256(9) 0.0302(9) 0.0007(7) 0.0125(7) -0.0016(7) C7 0.0392(10) 0.0267(9) 0.0330(10) -0.0062(7) 0.0157(8) -0.0096(7) C8 0.0464(11) 0.0272(9) 0.0509(12) 0.0034(8) 0.0295(10) 0.0083(8) C9 0.0527(11) 0.0320(10) 0.0367(11) 0.0009(8) 0.0282(9) -0.0017(8) C10 0.0225(8) 0.0236(8) 0.0243(9) -0.0018(6) 0.0105(7) 0.0017(6) C11 0.0247(8) 0.0226(8) 0.0282(9) 0.0004(7) 0.0079(7) 0.0032(6) C12 0.0258(8) 0.0227(8) 0.0344(10) -0.0017(7) 0.0104(7) -0.0034(6) C13 0.0208(8) 0.0263(8) 0.0287(9) -0.0061(7) 0.0058(7) 0.0019(6) C14 0.0281(9) 0.0260(9) 0.0264(9) 0.0024(7) 0.0069(7) 0.0059(7) C15 0.0265(8) 0.0235(8) 0.0306(9) 0.0002(7) 0.0128(7) 0.0009(7) C16 0.0273(10) 0.0343(11) 0.0729(16) 0.0011(10) -0.0078(10) 0.0054(8) C17 0.0234(8) 0.0227(8) 0.0225(8) 0.0003(6) 0.0087(7) -0.0004(6) C18 0.0239(8) 0.0211(8) 0.0303(9) -0.0011(6) 0.0098(7) -0.0030(6) C19 0.0213(8) 0.0270(9) 0.0292(9) -0.0009(7) 0.0081(7) -0.0019(7) C20 0.0292(9) 0.0232(8) 0.0246(9) 0.0020(6) 0.0076(7) 0.0029(7) C21 0.0321(9) 0.0210(8) 0.0370(11) 0.0012(7) -0.0008(8) -0.0066(7) C22 0.0247(8) 0.0254(9) 0.0320(10) 0.0023(7) 0.0009(7) -0.0039(7) C23 0.0306(9) 0.0325(10) 0.0398(11) 0.0060(8) 0.0069(8) 0.0093(8) B1 0.0245(9) 0.0203(9) 0.0282(10) -0.0010(7) 0.0108(8) 0.0014(7) B2 0.0254(9) 0.0222(9) 0.0259(10) -0.0011(7) 0.0119(8) 0.0008(7) B3 0.0228(9) 0.0229(9) 0.0222(9) -0.0027(7) 0.0095(8) -0.0024(7) N1 0.0361(8) 0.0218(7) 0.0339(8) 0.0005(6) 0.0201(7) -0.0004(6) O1 0.0222(6) 0.0228(6) 0.0400(7) 0.0043(5) 0.0102(5) 0.0003(4) O2 0.0212(6) 0.0208(6) 0.0333(7) 0.0009(5) 0.0083(5) -0.0009(4) O3 0.0222(6) 0.0202(6) 0.0311(6) 0.0009(5) 0.0098(5) 0.0001(4) O4 0.0222(6) 0.0299(6) 0.0489(8) -0.0022(6) 0.0011(6) 0.0014(5) O5 0.0334(7) 0.0224(6) 0.0385(7) 0.0027(5) -0.0002(6) 0.0042(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 C1 C2 1.384(2) . ? C1 C6 1.395(2) . ? C1 B1 1.599(2) . ? C2 C3 1.390(2) . ? C2 H2 0.9500 . ? C3 C4 1.383(2) . ? C3 H3 0.9500 . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.383(2) . ? C5 H5 0.9500 . ? C6 C7 1.504(2) . ? C7 N1 1.501(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 N1 1.489(2) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 N1 1.482(2) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.393(2) . ? C10 C11 1.401(2) . ? C10 B2 1.553(2) . ? C11 C12 1.373(2) . ? C11 H11 0.9500 . ? C12 C13 1.389(2) . ? C12 H12 0.9500 . ? C13 O4 1.3702(18) . ? C13 C14 1.389(2) . ? C14 C15 1.386(2) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C16 O4 1.418(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.392(2) . ? C17 C22 1.395(2) . ? C17 B3 1.553(2) . ? C18 C19 1.384(2) . ? C18 H18 0.9500 . ? C19 C20 1.381(2) . ? C19 H19 0.9500 . ? C20 O5 1.3661(18) . ? C20 C21 1.395(2) . ? C21 C22 1.376(2) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 O5 1.426(2) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? B1 O1 1.447(2) . ? B1 O3 1.457(2) . ? B1 N1 1.701(2) . ? B2 O1 1.352(2) . ? B2 O2 1.385(2) . ? B3 O3 1.3502(19) . ? B3 O2 1.393(2) . ? 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 C2 C1 C6 117.91(15) . . ? C2 C1 B1 131.64(15) . . ? C6 C1 B1 110.45(14) . . ? C1 C2 C3 120.73(16) . . ? C1 C2 H2 119.6 . . ? C3 C2 H2 119.6 . . ? C4 C3 C2 120.28(16) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C3 C4 C5 120.11(16) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C6 C5 C4 118.80(17) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C6 C1 122.16(16) . . ? C5 C6 C7 125.75(16) . . ? C1 C6 C7 112.09(14) . . ? N1 C7 C6 104.49(13) . . ? N1 C7 H7A 110.9 . . ? C6 C7 H7A 110.9 . . ? N1 C7 H7B 110.9 . . ? C6 C7 H7B 110.9 . . ? H7A C7 H7B 108.9 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 116.54(14) . . ? C15 C10 B2 120.60(14) . . ? C11 C10 B2 122.86(14) . . ? C12 C11 C10 122.17(15) . . ? C12 C11 H11 118.9 . . ? C10 C11 H11 118.9 . . ? C11 C12 C13 119.76(15) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? O4 C13 C12 115.68(14) . . ? O4 C13 C14 124.32(14) . . ? C12 C13 C14 119.99(15) . . ? C15 C14 C13 119.07(15) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C10 122.45(15) . . ? C14 C15 H15 118.8 . . ? C10 C15 H15 118.8 . . ? O4 C16 H16A 109.5 . . ? O4 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O4 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C18 C17 C22 116.22(14) . . ? C18 C17 B3 122.46(14) . . ? C22 C17 B3 121.32(14) . . ? C19 C18 C17 122.94(14) . . ? C19 C18 H18 118.5 . . ? C17 C18 H18 118.5 . . ? C20 C19 C18 119.22(14) . . ? C20 C19 H19 120.4 . . ? C18 C19 H19 120.4 . . ? O5 C20 C19 125.02(14) . . ? O5 C20 C21 115.53(14) . . ? C19 C20 C21 119.45(14) . . ? C22 C21 C20 120.00(15) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C21 C22 C17 122.13(15) . . ? C21 C22 H22 118.9 . . ? C17 C22 H22 118.9 . . ? O5 C23 H23A 109.5 . . ? O5 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O5 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? O1 B1 O3 113.18(13) . . ? O1 B1 C1 116.79(14) . . ? O3 B1 C1 114.36(13) . . ? O1 B1 N1 107.17(12) . . ? O3 B1 N1 106.15(12) . . ? C1 B1 N1 96.98(11) . . ? O1 B2 O2 120.54(14) . . ? O1 B2 C10 120.14(14) . . ? O2 B2 C10 119.32(14) . . ? O3 B3 O2 120.60(14) . . ? O3 B3 C17 121.76(14) . . ? O2 B3 C17 117.63(13) . . ? C9 N1 C8 109.22(13) . . ? C9 N1 C7 111.01(13) . . ? C8 N1 C7 108.74(13) . . ? C9 N1 B1 113.98(12) . . ? C8 N1 B1 109.96(13) . . ? C7 N1 B1 103.75(12) . . ? B2 O1 B1 122.85(13) . . ? B2 O2 B3 119.60(13) . . ? B3 O3 B1 122.52(13) . . ? C13 O4 C16 117.24(13) . . ? C20 O5 C23 117.50(13) . . ? _diffrn_measured_fraction_theta_max 0.886 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.318 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.052 data_Iovinecompd3c _database_code_depnum_ccdc_archive 'CCDC 671274' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common pmiz6d _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 B3 N O5' _chemical_formula_weight 452.90 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 P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.0525(12) _cell_length_b 12.2950(11) _cell_length_c 16.2138(14) _cell_angle_alpha 90.00 _cell_angle_beta 111.504(2) _cell_angle_gamma 90.00 _cell_volume 2420.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 208(2) _cell_measurement_reflns_used 3999 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 26.08 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.243 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 952 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9900 _exptl_absorpt_correction_T_max 0.9967 _exptl_absorpt_process_details SADABS _diffrn_refln_scan_width 0.3 _diffrn_refln_scan_rate 10 _space_group.centring_type primitive _space_group.IT_number 14 _exptl_special_details ; ? ; _diffrn_ambient_temperature 208(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_reflns_number 14020 _diffrn_reflns_av_R_equivalents 0.0351 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4286 _reflns_number_gt 2754 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution SIR-2004 _computing_structure_refinement SHELXL-97 _computing_molecular_graphics ORTEP-32 _computing_publication_material WinGX _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^)+(0.1071P)^2^+0.3728P] 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 4286 _refine_ls_number_parameters 311 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0943 _refine_ls_R_factor_gt 0.0616 _refine_ls_wR_factor_ref 0.1975 _refine_ls_wR_factor_gt 0.1710 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 C1 C 0.7911(2) 0.4995(2) 0.86680(17) 0.0578(7) Uani 1 1 d . . . C2 C 0.8347(3) 0.4817(3) 0.8011(2) 0.0787(9) Uani 1 1 d . . . H2 H 0.8339 0.4114 0.7782 0.094 Uiso 1 1 calc R . . C3 C 0.8800(3) 0.5688(3) 0.7689(2) 0.0844(10) Uani 1 1 d . . . H3 H 0.9096 0.5567 0.7248 0.101 Uiso 1 1 calc R . . C4 C 0.8804(3) 0.6717(4) 0.8027(3) 0.0933(11) Uani 1 1 d . . . H4 H 0.9104 0.7294 0.7810 0.112 Uiso 1 1 calc R . . C5 C 0.8385(3) 0.6923(3) 0.8668(2) 0.0803(10) Uani 1 1 d . . . H5 H 0.8399 0.7629 0.8894 0.096 Uiso 1 1 calc R . . C6 C 0.7938(2) 0.6059(2) 0.89787(18) 0.0609(7) Uani 1 1 d . . . C7 C 0.7407(2) 0.6150(2) 0.96390(19) 0.0682(8) Uani 1 1 d . . . H7A H 0.6637 0.6378 0.9356 0.082 Uiso 1 1 calc R . . H7B H 0.7796 0.6677 1.0101 0.082 Uiso 1 1 calc R . . C8 C 0.6620(3) 0.4883(3) 1.0401(2) 0.0973(12) Uani 1 1 d . . . H8A H 0.6739 0.5391 1.0885 0.146 Uiso 1 1 calc R . . H8B H 0.6661 0.4145 1.0622 0.146 Uiso 1 1 calc R . . H8C H 0.5899 0.5007 0.9948 0.146 Uiso 1 1 calc R . . C9 C 0.8582(3) 0.4893(3) 1.07215(19) 0.0767(9) Uani 1 1 d . . . H9A H 0.9149 0.5024 1.0479 0.115 Uiso 1 1 calc R . . H9B H 0.8647 0.4155 1.0946 0.115 Uiso 1 1 calc R . . H9C H 0.8670 0.5401 1.1201 0.115 Uiso 1 1 calc R . . C10 C 0.7933(2) 0.1235(2) 0.99870(16) 0.0546(7) Uani 1 1 d . . . C11 C 0.7381(2) 0.0264(2) 0.99792(19) 0.0648(8) Uani 1 1 d . . . H11 H 0.6618 0.0227 0.9662 0.078 Uiso 1 1 calc R . . C12 C 0.7926(2) -0.0648(2) 1.04249(18) 0.0635(8) Uani 1 1 d . . . H12 H 0.7532 -0.1293 1.0405 0.076 Uiso 1 1 calc R . . C13 C 0.9052(2) -0.0616(2) 1.09022(16) 0.0558(7) Uani 1 1 d . . . C14 C 0.9606(2) 0.0347(2) 1.09161(18) 0.0606(7) Uani 1 1 d . . . H14 H 1.0368 0.0384 1.1238 0.073 Uiso 1 1 calc R . . C15 C 0.9060(2) 0.1249(2) 1.04676(17) 0.0593(7) Uani 1 1 d . . . H15 H 0.9459 0.1892 1.0486 0.071 Uiso 1 1 calc R . . C16 C 0.9611(2) -0.1607(2) 1.14163(19) 0.0646(8) Uani 1 1 d . . . C17 C 1.0786(3) -0.1532(3) 1.1996(2) 0.0861(10) Uani 1 1 d . . . H17A H 1.1014 -0.2207 1.2322 0.129 Uiso 1 1 calc R . . H17B H 1.0886 -0.0936 1.2411 0.129 Uiso 1 1 calc R . . H17C H 1.1227 -0.1404 1.1637 0.129 Uiso 1 1 calc R . . C18 C 0.4347(2) 0.30364(19) 0.81294(16) 0.0495(6) Uani 1 1 d . . . C19 C 0.3732(2) 0.3899(2) 0.76648(16) 0.0512(6) Uani 1 1 d . . . H19 H 0.4073 0.4577 0.7685 0.061 Uiso 1 1 calc R . . C20 C 0.2625(2) 0.3788(2) 0.71708(17) 0.0562(7) Uani 1 1 d . . . H20 H 0.2223 0.4392 0.6862 0.067 Uiso 1 1 calc R . . C21 C 0.2097(2) 0.2802(2) 0.71237(18) 0.0559(7) Uani 1 1 d . . . C22 C 0.2711(2) 0.1930(2) 0.7583(2) 0.0732(9) Uani 1 1 d . . . H22 H 0.2374 0.1249 0.7558 0.088 Uiso 1 1 calc R . . C23 C 0.3807(2) 0.2052(2) 0.8074(2) 0.0695(8) Uani 1 1 d . . . H23 H 0.4208 0.1449 0.8384 0.083 Uiso 1 1 calc R . . C24 C 0.0902(2) 0.2642(2) 0.6592(2) 0.0697(8) Uani 1 1 d . . . C25 C 0.0206(3) 0.3607(3) 0.6189(3) 0.1273(18) Uani 1 1 d . . . H25A H 0.0469 0.3942 0.5762 0.191 Uiso 1 1 calc R . . H25B H 0.0249 0.4127 0.6650 0.191 Uiso 1 1 calc R . . H25C H -0.0552 0.3378 0.5893 0.191 Uiso 1 1 calc R . . B1 B 0.7333(2) 0.4213(2) 0.91569(19) 0.0507(7) Uani 1 1 d . . . B2 B 0.7312(2) 0.2283(2) 0.95167(19) 0.0541(7) Uani 1 1 d . . . B3 B 0.5620(2) 0.3155(2) 0.86687(19) 0.0511(7) Uani 1 1 d . . . N1 N 0.74797(18) 0.50445(18) 1.00147(14) 0.0582(6) Uani 1 1 d . . . O1 O 0.78701(13) 0.31997(14) 0.95123(12) 0.0585(5) Uani 1 1 d . . . O2 O 0.61737(14) 0.22441(14) 0.91205(12) 0.0578(5) Uani 1 1 d . . . O3 O 0.61504(13) 0.40921(13) 0.86765(11) 0.0534(5) Uani 1 1 d . . . O4 O 0.90938(19) -0.24401(17) 1.13600(15) 0.0894(7) Uani 1 1 d . . . O5 O 0.04961(16) 0.17387(17) 0.64752(17) 0.0889(7) 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 C1 0.0420(14) 0.0728(19) 0.0528(14) 0.0076(13) 0.0106(12) 0.0101(13) C2 0.068(2) 0.089(2) 0.0741(19) 0.0083(17) 0.0210(17) 0.0171(17) C3 0.061(2) 0.115(3) 0.079(2) 0.028(2) 0.0276(17) 0.004(2) C4 0.074(2) 0.111(3) 0.085(2) 0.020(2) 0.017(2) -0.019(2) C5 0.068(2) 0.077(2) 0.079(2) 0.0080(17) 0.0062(18) -0.0185(16) C6 0.0473(15) 0.0547(17) 0.0673(16) 0.0093(13) 0.0051(13) -0.0057(12) C7 0.0651(18) 0.0569(17) 0.0689(17) -0.0072(14) 0.0083(15) 0.0023(14) C8 0.091(3) 0.129(3) 0.085(2) -0.024(2) 0.047(2) -0.014(2) C9 0.077(2) 0.074(2) 0.0570(16) -0.0040(14) -0.0022(15) -0.0009(16) C10 0.0501(15) 0.0487(15) 0.0563(14) -0.0024(12) 0.0094(12) 0.0011(12) C11 0.0465(16) 0.0540(16) 0.0735(18) -0.0035(13) -0.0018(14) -0.0022(12) C12 0.0573(17) 0.0424(14) 0.0720(17) -0.0033(13) 0.0014(14) -0.0045(12) C13 0.0525(16) 0.0484(15) 0.0561(14) -0.0078(12) 0.0079(12) 0.0032(12) C14 0.0436(15) 0.0616(17) 0.0687(17) 0.0017(13) 0.0112(13) 0.0018(13) C15 0.0456(15) 0.0560(16) 0.0678(16) 0.0052(13) 0.0108(13) -0.0015(12) C16 0.0609(18) 0.0503(16) 0.0687(17) -0.0079(13) 0.0073(14) 0.0040(14) C17 0.063(2) 0.069(2) 0.099(2) 0.0116(18) -0.0023(18) 0.0117(16) C18 0.0442(14) 0.0450(14) 0.0552(14) -0.0056(11) 0.0133(12) 0.0009(11) C19 0.0470(14) 0.0460(14) 0.0553(14) -0.0029(11) 0.0124(12) -0.0029(11) C20 0.0520(16) 0.0476(15) 0.0601(15) 0.0004(12) 0.0102(13) 0.0076(12) C21 0.0440(14) 0.0496(15) 0.0673(16) -0.0049(12) 0.0124(12) 0.0003(12) C22 0.0475(17) 0.0466(16) 0.107(2) 0.0062(15) 0.0070(16) -0.0066(13) C23 0.0483(16) 0.0480(16) 0.096(2) 0.0107(14) 0.0076(15) 0.0026(13) C24 0.0467(16) 0.0605(18) 0.089(2) -0.0104(15) 0.0095(15) -0.0003(14) C25 0.051(2) 0.076(2) 0.199(4) 0.005(3) -0.020(2) 0.0103(17) B1 0.0429(16) 0.0474(16) 0.0562(16) -0.0027(13) 0.0114(13) -0.0005(13) B2 0.0484(17) 0.0530(18) 0.0517(16) -0.0031(13) 0.0076(14) 0.0005(14) B3 0.0457(17) 0.0488(17) 0.0555(16) -0.0054(13) 0.0148(14) -0.0005(13) N1 0.0545(13) 0.0603(14) 0.0542(12) -0.0039(10) 0.0133(11) -0.0016(10) O1 0.0444(10) 0.0492(10) 0.0716(11) 0.0040(8) 0.0090(9) -0.0009(8) O2 0.0437(10) 0.0494(10) 0.0693(11) 0.0026(8) 0.0078(9) -0.0003(8) O3 0.0410(9) 0.0471(10) 0.0632(10) -0.0007(8) 0.0086(8) -0.0005(8) O4 0.0839(16) 0.0544(13) 0.0957(16) 0.0021(11) -0.0074(13) -0.0020(11) O5 0.0521(12) 0.0644(14) 0.1263(19) -0.0141(12) 0.0045(12) -0.0063(10) _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 C1 C2 1.396(4) . ? C1 C6 1.398(4) . ? C1 B1 1.600(4) . ? C2 C3 1.412(5) . ? C2 H2 0.9400 . ? C3 C4 1.378(5) . ? C3 H3 0.9400 . ? C4 C5 1.363(5) . ? C4 H4 0.9400 . ? C5 C6 1.392(4) . ? C5 H5 0.9400 . ? C6 C7 1.477(4) . ? C7 N1 1.479(4) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C8 N1 1.485(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C9 N1 1.487(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 H9C 0.9700 . ? C10 C15 1.391(3) . ? C10 C11 1.391(4) . ? C10 B2 1.564(4) . ? C11 C12 1.381(4) . ? C11 H11 0.9400 . ? C12 C13 1.389(4) . ? C12 H12 0.9400 . ? C13 C14 1.382(4) . ? C13 C16 1.505(4) . ? C14 C15 1.374(4) . ? C14 H14 0.9400 . ? C15 H15 0.9400 . ? C16 O4 1.212(3) . ? C16 C17 1.479(4) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C17 H17C 0.9700 . ? C18 C19 1.376(3) . ? C18 C23 1.387(4) . ? C18 B3 1.575(4) . ? C19 C20 1.378(3) . ? C19 H19 0.9400 . ? C20 C21 1.384(3) . ? C20 H20 0.9400 . ? C21 C22 1.382(4) . ? C21 C24 1.492(4) . ? C22 C23 1.366(4) . ? C22 H22 0.9400 . ? C23 H23 0.9400 . ? C24 O5 1.215(3) . ? C24 C25 1.491(4) . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? C25 H25C 0.9700 . ? B1 O1 1.442(3) . ? B1 O3 1.460(3) . ? B1 N1 1.680(4) . ? B2 O1 1.343(3) . ? B2 O2 1.387(3) . ? B3 O3 1.342(3) . ? B3 O2 1.388(3) . ? 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 C2 C1 C6 117.3(3) . . ? C2 C1 B1 133.0(3) . . ? C6 C1 B1 109.8(2) . . ? C1 C2 C3 120.4(3) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 119.3(3) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C5 C4 C3 122.0(4) . . ? C5 C4 H4 119.0 . . ? C3 C4 H4 119.0 . . ? C4 C5 C6 118.2(3) . . ? C4 C5 H5 120.9 . . ? C6 C5 H5 120.9 . . ? C5 C6 C1 122.8(3) . . ? C5 C6 C7 125.1(3) . . ? C1 C6 C7 112.1(2) . . ? C6 C7 N1 104.6(2) . . ? C6 C7 H7A 110.8 . . ? N1 C7 H7A 110.8 . . ? C6 C7 H7B 110.8 . . ? N1 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? N1 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? N1 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? N1 C9 H9A 109.5 . . ? N1 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? N1 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 117.0(2) . . ? C15 C10 B2 121.0(2) . . ? C11 C10 B2 122.0(2) . . ? C12 C11 C10 121.8(3) . . ? C12 C11 H11 119.1 . . ? C10 C11 H11 119.1 . . ? C11 C12 C13 120.3(3) . . ? C11 C12 H12 119.8 . . ? C13 C12 H12 119.8 . . ? C14 C13 C12 118.3(2) . . ? C14 C13 C16 122.7(2) . . ? C12 C13 C16 119.0(2) . . ? C15 C14 C13 121.1(3) . . ? C15 C14 H14 119.5 . . ? C13 C14 H14 119.5 . . ? C14 C15 C10 121.5(3) . . ? C14 C15 H15 119.2 . . ? C10 C15 H15 119.2 . . ? O4 C16 C17 121.3(3) . . ? O4 C16 C13 120.0(3) . . ? C17 C16 C13 118.7(3) . . ? C16 C17 H17A 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C19 C18 C23 117.1(2) . . ? C19 C18 B3 121.2(2) . . ? C23 C18 B3 121.7(2) . . ? C18 C19 C20 121.3(2) . . ? C18 C19 H19 119.3 . . ? C20 C19 H19 119.3 . . ? C19 C20 C21 120.9(2) . . ? C19 C20 H20 119.6 . . ? C21 C20 H20 119.6 . . ? C22 C21 C20 118.1(2) . . ? C22 C21 C24 119.1(2) . . ? C20 C21 C24 122.8(2) . . ? C23 C22 C21 120.4(3) . . ? C23 C22 H22 119.8 . . ? C21 C22 H22 119.8 . . ? C22 C23 C18 122.2(3) . . ? C22 C23 H23 118.9 . . ? C18 C23 H23 118.9 . . ? O5 C24 C25 119.9(3) . . ? O5 C24 C21 120.9(3) . . ? C25 C24 C21 119.2(3) . . ? C24 C25 H25A 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C24 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O1 B1 O3 112.9(2) . . ? O1 B1 C1 118.0(2) . . ? O3 B1 C1 113.3(2) . . ? O1 B1 N1 107.7(2) . . ? O3 B1 N1 106.3(2) . . ? C1 B1 N1 96.5(2) . . ? O1 B2 O2 121.2(2) . . ? O1 B2 C10 120.6(2) . . ? O2 B2 C10 118.2(2) . . ? O3 B3 O2 121.4(2) . . ? O3 B3 C18 121.4(2) . . ? O2 B3 C18 117.2(2) . . ? C7 N1 C8 110.6(2) . . ? C7 N1 C9 109.3(2) . . ? C8 N1 C9 109.0(2) . . ? C7 N1 B1 104.36(19) . . ? C8 N1 B1 113.2(2) . . ? C9 N1 B1 110.2(2) . . ? B2 O1 B1 122.8(2) . . ? B2 O2 B3 118.6(2) . . ? B3 O3 B1 122.3(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 0.340 _refine_diff_density_min -0.168 _refine_diff_density_rms 0.047