Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_compound _database_code_CSD 163357 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Marco Bandini' 'Pier Giorgio Cozzi' 'Magda Monari' 'Rossana Perciaccante' 'Simona Selva' 'Achille Umani-Ronchi' _publ_contact_author_name 'Prof Achille Umani-Ronchi' _publ_contact_author_address ; Prof Achille Umani-Ronchi Dipartimento Chimico "G. Ciamician" Universita di Bologna Via Selmi 2 Bologna 40126 ITALY ; _publ_contact_author_email 'UMANI@CIAM.UNIBO.IT' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H21 B N2 O4' _chemical_formula_weight 328.17 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' 'O' 'O' 0.0106 0.0060 '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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.9871(3) _cell_length_b 9.4340(4) _cell_length_c 11.1411(4) _cell_angle_alpha 67.378(2) _cell_angle_beta 75.067(2) _cell_angle_gamma 77.487(2) _cell_volume 835.12(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2422 _cell_measurement_theta_min 2.36 _cell_measurement_theta_max 24.62 _exptl_crystal_description parallelepiped _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.305 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 1.00 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker SMART 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 11678 _diffrn_reflns_av_R_equivalents 0.0293 _diffrn_reflns_av_sigmaI/netI 0.0536 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.02 _diffrn_reflns_theta_max 30.06 _reflns_number_total 4866 _reflns_number_gt 2210 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SIR97 (Altomare, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP (Johnson, 1976)' _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 w=1/[\s^2^(Fo^2^)+(0.0638P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4860 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0991 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1260 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 0.814 _refine_ls_restrained_S_all 0.831 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly #_atom_site_disorder_group B1 B 0.5725(2) 0.9387(2) 0.2442(2) 0.0458(4) Uani 1 d . . O1 O 0.46971(13) 1.34049(12) 0.02685(12) 0.0659(3) Uani 1 d . . O2 O 0.17048(13) 1.02677(15) 0.41344(13) 0.0759(4) Uani 1 d . . O3 O 0.70494(11) 0.89822(12) 0.31248(10) 0.0532(3) Uani 1 d . . O4 O 0.59485(10) 0.81892(11) 0.18357(10) 0.0474(3) Uani 1 d . . N1 N 0.57055(13) 1.10257(13) 0.13846(12) 0.0456(3) Uani 1 d . . N2 N 0.41502(13) 0.93967(14) 0.34195(12) 0.0492(3) Uani 1 d . . C1 C 0.7042(2) 1.1677(2) 0.03339(15) 0.0498(4) Uani 1 d . . C2 C 0.6189(2) 1.3133(2) -0.0546(2) 0.0648(5) Uani 1 d . . H2A H 0.5964(22) 1.2969(22) -0.1351(20) 0.094(6) Uiso 1 d . . H2B H 0.6704(20) 1.4053(22) -0.0823(17) 0.074(5) Uiso 1 d . . C3 C 0.4473(2) 1.2083(2) 0.1293(2) 0.0520(4) Uani 1 d . . C4 C 0.3070(2) 1.1919(2) 0.2161(2) 0.0632(5) Uani 1 d . . H4 H 0.2146(23) 1.2754(22) 0.2071(17) 0.088(6) Uiso 1 d . . C5 C 0.3002(2) 1.0545(2) 0.3208(2) 0.0562(4) Uani 1 d . . C6 C 0.2085(2) 0.8860(3) 0.5202(2) 0.0775(6) Uani 1 d . . H6A H 0.1227(24) 0.8245(24) 0.5518(20) 0.091(6) Uiso 1 d . . H6B H 0.2127(26) 0.9284(27) 0.5966(24) 0.130(9) Uiso 1 d . . C7 C 0.3607(2) 0.8075(2) 0.4621(2) 0.0535(4) Uani 1 d . . C8 C 0.3340(3) 0.6788(3) 0.4229(2) 0.0718(5) Uani 1 d . . H8A H 0.2566(25) 0.7247(24) 0.3612(21) 0.101(7) Uiso 1 d . . H8B H 0.2878(21) 0.5940(20) 0.5032(18) 0.078(5) Uiso 1 d . . H8C H 0.4374(26) 0.6286(24) 0.3829(21) 0.104(7) Uiso 1 d . . C9 C 0.4691(3) 0.7472(3) 0.5594(2) 0.0731(5) Uani 1 d . . H9A H 0.4163(23) 0.6652(23) 0.6435(22) 0.096(6) Uiso 1 d . . H9B H 0.5689(25) 0.6909(22) 0.5247(19) 0.088(6) Uiso 1 d . . H9C H 0.4826(25) 0.8312(28) 0.5769(20) 0.102(8) Uiso 1 d . . C10 C 0.8161(2) 1.2074(3) 0.0936(2) 0.0721(5) Uani 1 d . . H10A H 0.7534(24) 1.2808(24) 0.1417(20) 0.097(7) Uiso 1 d . . H10B H 0.8657(23) 1.1123(24) 0.1602(20) 0.093(7) Uiso 1 d . . H10C H 0.8955(21) 1.2599(21) 0.0252(19) 0.076(5) Uiso 1 d . . C11 C 0.7850(3) 1.0613(2) -0.0426(2) 0.0650(5) Uani 1 d . . H11A H 0.8398(21) 0.9649(22) 0.0144(18) 0.078(5) Uiso 1 d . . H11B H 0.8653(22) 1.1099(20) -0.1165(19) 0.078(5) Uiso 1 d . . H11C H 0.7103(23) 1.0335(22) -0.0751(18) 0.083(6) Uiso 1 d . . C12 C 0.7251(2) 0.7216(2) 0.21551(15) 0.0485(4) Uani 1 d . . C13 C 0.7900(2) 0.7682(2) 0.2929(2) 0.0512(4) Uani 1 d . . C14 C 0.9220(2) 0.6859(2) 0.3394(2) 0.0675(5) Uani 1 d . . H14 H 0.9609(19) 0.7209(20) 0.3969(17) 0.069(5) Uiso 1 d . . C15 C 0.9893(2) 0.5558(2) 0.3039(2) 0.0786(6) Uani 1 d . . H15 H 1.0870(23) 0.4979(22) 0.3349(18) 0.087(6) Uiso 1 d . . C16 C 0.9258(2) 0.5126(2) 0.2262(2) 0.0768(6) Uani 1 d . . H16 H 0.9777(25) 0.4210(26) 0.2048(20) 0.109(7) Uiso 1 d . . C17 C 0.7916(2) 0.5950(2) 0.1803(2) 0.0610(5) Uani 1 d . . H17 H 0.7468(21) 0.5630(22) 0.1243(18) 0.083(6) Uiso 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 B1 0.0379(9) 0.0443(9) 0.0563(10) -0.0196(8) -0.0080(8) -0.0053(7) O1 0.0608(7) 0.0420(6) 0.0819(8) -0.0159(6) -0.0069(6) 0.0004(5) O2 0.0421(6) 0.0828(9) 0.0880(9) -0.0309(8) 0.0097(6) -0.0028(6) O3 0.0424(6) 0.0580(6) 0.0608(7) -0.0202(5) -0.0121(5) -0.0081(5) O4 0.0376(5) 0.0413(5) 0.0635(6) -0.0209(5) -0.0111(5) 0.0005(4) N1 0.0382(6) 0.0407(6) 0.0572(7) -0.0202(6) -0.0040(5) -0.0041(5) N2 0.0386(6) 0.0483(7) 0.0592(8) -0.0209(6) -0.0037(6) -0.0057(5) C1 0.0456(8) 0.0460(8) 0.0547(9) -0.0177(7) -0.0014(7) -0.0096(7) C2 0.0625(11) 0.0481(10) 0.0729(12) -0.0154(9) -0.0040(9) -0.0069(8) C3 0.0492(9) 0.0406(8) 0.0654(10) -0.0203(7) -0.0096(8) -0.0031(7) C4 0.0443(9) 0.0516(10) 0.0838(12) -0.0241(9) -0.0044(9) 0.0054(8) C5 0.0381(8) 0.0596(10) 0.0719(11) -0.0318(9) 0.0002(8) -0.0052(7) C6 0.0586(12) 0.0789(14) 0.0749(13) -0.0214(11) 0.0108(10) -0.0074(10) C7 0.0453(8) 0.0582(10) 0.0549(9) -0.0195(8) 0.0007(7) -0.0153(7) C8 0.0786(14) 0.0710(13) 0.0677(12) -0.0246(11) 0.0057(11) -0.0367(11) C9 0.0708(14) 0.0821(15) 0.0618(12) -0.0163(11) -0.0106(10) -0.0197(12) C10 0.0624(12) 0.0862(15) 0.0714(13) -0.0247(12) -0.0033(11) -0.0340(11) C11 0.0670(12) 0.0580(11) 0.0605(11) -0.0225(9) 0.0052(10) -0.0067(10) C12 0.0354(7) 0.0405(8) 0.0579(9) -0.0097(7) -0.0027(7) -0.0029(6) C13 0.0348(7) 0.0495(9) 0.0571(9) -0.0085(7) -0.0039(7) -0.0057(7) C14 0.0418(9) 0.0759(13) 0.0670(11) -0.0036(9) -0.0114(8) -0.0109(9) C15 0.0419(10) 0.0677(12) 0.0893(14) 0.0003(11) -0.0072(10) 0.0091(9) C16 0.0537(11) 0.0549(11) 0.0915(14) -0.0099(10) -0.0011(10) 0.0094(9) C17 0.0506(10) 0.0452(9) 0.0726(11) -0.0162(8) -0.0013(9) 0.0020(7) _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 O3 1.479(2) . ? B1 O4 1.481(2) . ? B1 N1 1.541(2) . ? B1 N2 1.548(2) . ? O1 C3 1.339(2) . ? O1 C2 1.446(2) . ? O2 C5 1.341(2) . ? O2 C6 1.447(2) . ? O3 C13 1.361(2) . ? O4 C12 1.355(2) . ? N1 C3 1.316(2) . ? N1 C1 1.494(2) . ? N2 C5 1.319(2) . ? N2 C7 1.493(2) . ? C1 C11 1.508(2) . ? C1 C10 1.519(2) . ? C1 C2 1.527(2) . ? C2 H2A 1.04(2) . ? C2 H2B 0.98(2) . ? C3 C4 1.375(2) . ? C4 C5 1.370(2) . ? C4 H4 1.01(2) . ? C6 C7 1.520(2) . ? C6 H6A 0.98(2) . ? C6 H6B 1.08(2) . ? C7 C9 1.509(2) . ? C7 C8 1.520(2) . ? C8 H8A 1.02(2) . ? C8 H8B 1.01(2) . ? C8 H8C 1.02(2) . ? C9 H9A 1.04(2) . ? C9 H9B 1.00(2) . ? C9 H9C 0.92(2) . ? C10 H10A 1.02(2) . ? C10 H10B 1.02(2) . ? C10 H10C 0.96(2) . ? C11 H11A 1.00(2) . ? C11 H11B 0.98(2) . ? C11 H11C 0.96(2) . ? C12 C17 1.367(2) . ? C12 C13 1.392(2) . ? C13 C14 1.373(2) . ? C14 C15 1.399(3) . ? C14 H14 0.99(2) . ? C15 C16 1.367(3) . ? C15 H15 1.00(2) . ? C16 C17 1.388(3) . ? C16 H16 0.97(2) . ? C17 H17 0.98(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 O3 B1 O4 104.55(11) . . ? O3 B1 N1 111.81(12) . . ? O4 B1 N1 111.32(12) . . ? O3 B1 N2 111.57(12) . . ? O4 B1 N2 111.93(11) . . ? N1 B1 N2 105.81(11) . . ? C3 O1 C2 107.21(12) . . ? C5 O2 C6 107.40(13) . . ? C13 O3 B1 107.03(11) . . ? C12 O4 B1 107.51(11) . . ? C3 N1 C1 109.48(12) . . ? C3 N1 B1 123.87(12) . . ? C1 N1 B1 126.64(11) . . ? C5 N2 C7 109.40(12) . . ? C5 N2 B1 123.57(13) . . ? C7 N2 B1 126.55(12) . . ? N1 C1 C11 112.26(13) . . ? N1 C1 C10 110.06(13) . . ? C11 C1 C10 111.7(2) . . ? N1 C1 C2 100.22(12) . . ? C11 C1 C2 110.53(15) . . ? C10 C1 C2 111.5(2) . . ? O1 C2 C1 105.51(13) . . ? O1 C2 H2A 106.6(11) . . ? C1 C2 H2A 112.2(11) . . ? O1 C2 H2B 107.1(10) . . ? C1 C2 H2B 113.1(10) . . ? H2A C2 H2B 111.8(15) . . ? N1 C3 O1 113.94(13) . . ? N1 C3 C4 125.15(15) . . ? O1 C3 C4 120.89(14) . . ? C5 C4 C3 115.69(15) . . ? C5 C4 H4 120.9(10) . . ? C3 C4 H4 123.4(11) . . ? N2 C5 O2 113.72(15) . . ? N2 C5 C4 125.26(14) . . ? O2 C5 C4 121.02(14) . . ? O2 C6 C7 105.47(14) . . ? O2 C6 H6A 108.8(12) . . ? C7 C6 H6A 114.0(12) . . ? O2 C6 H6B 102.8(12) . . ? C7 C6 H6B 116.4(12) . . ? H6A C6 H6B 108.5(17) . . ? N2 C7 C9 112.69(13) . . ? N2 C7 C8 110.53(13) . . ? C9 C7 C8 111.2(2) . . ? N2 C7 C6 100.66(13) . . ? C9 C7 C6 109.9(2) . . ? C8 C7 C6 111.4(2) . . ? C7 C8 H8A 107.8(12) . . ? C7 C8 H8B 110.6(10) . . ? H8A C8 H8B 108.1(15) . . ? C7 C8 H8C 110.3(12) . . ? H8A C8 H8C 113.8(17) . . ? H8B C8 H8C 106.3(15) . . ? C7 C9 H9A 107.3(11) . . ? C7 C9 H9B 111.4(11) . . ? H9A C9 H9B 105.9(15) . . ? C7 C9 H9C 106.7(14) . . ? H9A C9 H9C 111.8(16) . . ? H9B C9 H9C 113.7(18) . . ? C1 C10 H10A 107.0(11) . . ? C1 C10 H10B 112.6(11) . . ? H10A C10 H10B 108.6(16) . . ? C1 C10 H10C 110.1(11) . . ? H10A C10 H10C 108.6(16) . . ? H10B C10 H10C 109.7(15) . . ? C1 C11 H11A 111.2(10) . . ? C1 C11 H11B 111.2(10) . . ? H11A C11 H11B 105.7(14) . . ? C1 C11 H11C 109.8(11) . . ? H11A C11 H11C 108.9(15) . . ? H11B C11 H11C 109.9(15) . . ? O4 C12 C17 128.2(2) . . ? O4 C12 C13 110.19(13) . . ? C17 C12 C13 121.6(2) . . ? O3 C13 C14 128.3(2) . . ? O3 C13 C12 110.71(13) . . ? C14 C13 C12 121.0(2) . . ? C13 C14 C15 117.3(2) . . ? C13 C14 H14 118.0(10) . . ? C15 C14 H14 124.7(10) . . ? C16 C15 C14 121.2(2) . . ? C16 C15 H15 121.2(11) . . ? C14 C15 H15 117.5(11) . . ? C15 C16 C17 121.5(2) . . ? C15 C16 H16 117.5(13) . . ? C17 C16 H16 121.1(13) . . ? C12 C17 C16 117.5(2) . . ? C12 C17 H17 121.6(11) . . ? C16 C17 H17 120.9(11) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 30.06 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.196 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.043