# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/489 data_ASN81 _audit_creation_date 98-11-30 _audit_creation_method 'STADI4, X-RED' _audit_author_name 'J. Richter' _audit_contact_author 'J. Richter' _audit_contact_author_address ; STOE & CIE GmbH Hilpertstr. 10 D-64295 Darmstadt Germany ; _audit_contact_author_email 100066.3306@compuserve.com _audit_contact_author_fax '+49 6151 891293 ' _audit_contact_author_phone '+49 6151 891225 / 899174' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 B N O4' _chemical_formula_weight 357.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0311 0.0180 '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+1/2, z' 'x, -y+1/2, z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, -z' '-x, y-1/2, -z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 12.9858(4) _cell_length_b 11.7576(3) _cell_length_c 25.6292(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3913.1(2) _cell_formula_units_Z 8 _cell_measurement_temperature 180(2) _cell_measurement_reflns_used 75 _cell_measurement_theta_min 30.2 _cell_measurement_theta_max 39.6 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1536 _exptl_absorpt_coefficient_mu 0.664 _exptl_absorpt_correction_type Numerical _exptl_absorpt_correction_T_min 0.6915 _exptl_absorpt_correction_T_max 0.9488 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 -1.00 0.0800 0.00 0.00 1.00 0.0800 0.00 -1.00 0.00 0.2300 0.00 2.00 1.00 0.2300 -1.00 0.00 0.00 0.3000 1.00 0.00 1.00 0.2700 _exptl_special_details ; ? ; _diffrn_ambient_temperature 180(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_collimation '0.8 mm' _diffrn_radiation_detector 'NaI(Tl) scintillation counter' _diffrn_radiation_monochromator 'planar graphite' _diffrn_radiation_polarisn_norm 90 _diffrn_measurement_device_type 'STOE STADI4 4-circle-diffractometer' _diffrn_measurement_method ; Scan width (omega) = 1.45 - 1.70, scan ratio 2theta:omega = 1.00 I(Net) and sigma(I) calculated according to Blessing (1987) ; _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 60 _diffrn_standards_decay_% 0 _diffrn_reflns_number 5132 _diffrn_reflns_av_R_equivalents 0.0991 _diffrn_reflns_av_sigmaI/netI 0.0726 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.45 _diffrn_reflns_theta_max 64.54 _reflns_number_total 3170 _reflns_number_gt 2560 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'STADI4 (STOE, 1996)' _computing_cell_refinement 'STADI4 (STOE, 1996)' _computing_data_reduction 'X-RED (STOE, 1996)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ; PLATON98 (Spek, 1998) and ORTEX (McArdle, 1995) ; _computing_publication_material 'local program' _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^)+(0.0447P)^2^+1.7692P] 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 SHELXL _refine_ls_extinction_coef 0.00046(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3170 _refine_ls_number_parameters 263 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0582 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1098 _refine_ls_wR_factor_gt 0.0991 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 0.51751(16) 0.21434(18) 0.73750(7) 0.0312(5) Uani 1 1 d . . . O1 O 0.58367(9) 0.17820(10) 0.69305(4) 0.0307(3) Uani 1 1 d . . . O2 O 0.41254(9) 0.22502(11) 0.71492(5) 0.0354(3) Uani 1 1 d . . . C1 C 0.52165(12) 0.17455(14) 0.64952(6) 0.0259(4) Uani 1 1 d . . . C2 C 0.55040(13) 0.14556(14) 0.59942(7) 0.0283(4) Uani 1 1 d . . . C3 C 0.47079(14) 0.14687(16) 0.56224(7) 0.0351(4) Uani 1 1 d . . . H3 H 0.4865 0.1292 0.5270 0.042 Uiso 1 1 calc R . . C4 C 0.37035(15) 0.17308(17) 0.57542(8) 0.0386(5) Uani 1 1 d . . . H4 H 0.3188 0.1719 0.5491 0.046 Uiso 1 1 calc R . . C5 C 0.34275(14) 0.20130(16) 0.62644(7) 0.0353(4) Uani 1 1 d . . . H5 H 0.2737 0.2193 0.6355 0.042 Uiso 1 1 calc R . . C6 C 0.42031(13) 0.20174(15) 0.66290(7) 0.0290(4) Uani 1 1 d . . . C7 C 0.66081(13) 0.11518(15) 0.58556(7) 0.0308(4) Uani 1 1 d . . . H7 H 0.6974 0.0969 0.6189 0.037 Uiso 1 1 calc R . . C8 C 0.66698(16) 0.01019(18) 0.55085(8) 0.0434(5) Uani 1 1 d . . . H8A H 0.6300 -0.0528 0.5675 0.065 Uiso 1 1 calc R . . H8B H 0.7393 -0.0110 0.5458 0.065 Uiso 1 1 calc R . . H8C H 0.6356 0.0269 0.5169 0.065 Uiso 1 1 calc R . . C9 C 0.71633(17) 0.21568(18) 0.56061(10) 0.0539(6) Uani 1 1 d . . . H9A H 0.6818 0.2363 0.5279 0.081 Uiso 1 1 calc R . . H9B H 0.7879 0.1947 0.5533 0.081 Uiso 1 1 calc R . . H9C H 0.7149 0.2807 0.5845 0.081 Uiso 1 1 calc R . . O3 O 0.52389(9) 0.13056(10) 0.78012(4) 0.0308(3) Uani 1 1 d . . . O4 O 0.54769(10) 0.32443(10) 0.76125(4) 0.0335(3) Uani 1 1 d . . . C10 C 0.54655(12) 0.18968(15) 0.82495(7) 0.0267(4) Uani 1 1 d . . . C11 C 0.55513(13) 0.14677(15) 0.87468(7) 0.0293(4) Uani 1 1 d . A . C12 C 0.57444(14) 0.22747(17) 0.91391(7) 0.0360(4) Uani 1 1 d . . . H12 H 0.5795 0.2026 0.9491 0.043 Uiso 1 1 calc R . . C13 C 0.58627(15) 0.34185(17) 0.90293(7) 0.0390(5) Uani 1 1 d . . . H13 H 0.5989 0.3935 0.9307 0.047 Uiso 1 1 calc R . . C14 C 0.58008(14) 0.38295(16) 0.85202(7) 0.0349(4) Uani 1 1 d . . . H14 H 0.5892 0.4613 0.8443 0.042 Uiso 1 1 calc R . . C15 C 0.56024(13) 0.30470(15) 0.81354(7) 0.0279(4) Uani 1 1 d . . . C16 C 0.54255(15) 0.02081(16) 0.88583(8) 0.0379(5) Uani 1 1 d . . . H16A H 0.5529 -0.0227 0.8527 0.046 Uiso 0.545(13) 1 calc PR A 1 H16B H 0.5895 -0.0195 0.8610 0.046 Uiso 0.455(13) 1 d PR A 2 C17A C 0.4375(4) -0.0050(5) 0.9069(5) 0.068(2) Uani 0.545(13) 1 d P A 1 H17A H 0.4328 -0.0861 0.9153 0.102 Uiso 0.545(13) 1 calc PR A 1 H17B H 0.3855 0.0142 0.8807 0.102 Uiso 0.545(13) 1 calc PR A 1 H17C H 0.4255 0.0400 0.9385 0.102 Uiso 0.545(13) 1 calc PR A 1 C18A C 0.6252(6) -0.0182(6) 0.9266(3) 0.0603(18) Uani 0.545(13) 1 d P A 1 H18A H 0.6161 0.0246 0.9591 0.090 Uiso 0.545(13) 1 calc PR A 1 H18B H 0.6943 -0.0039 0.9126 0.090 Uiso 0.545(13) 1 calc PR A 1 H18C H 0.6171 -0.0997 0.9335 0.090 Uiso 0.545(13) 1 calc PR A 1 C17B C 0.4305(4) -0.0150(5) 0.8703(5) 0.058(2) Uani 0.455(13) 1 d P A 2 H17D H 0.4208 -0.0961 0.8774 0.086 Uiso 0.455(13) 1 calc PR A 2 H17E H 0.4199 -0.0005 0.8330 0.086 Uiso 0.455(13) 1 calc PR A 2 H17F H 0.3808 0.0294 0.8906 0.086 Uiso 0.455(13) 1 calc PR A 2 C18B C 0.5688(12) -0.0182(8) 0.9382(4) 0.080(3) Uani 0.455(13) 1 d P A 2 H18D H 0.6408 0.0007 0.9458 0.120 Uiso 0.455(13) 1 calc PR A 2 H18E H 0.5592 -0.1007 0.9404 0.120 Uiso 0.455(13) 1 calc PR A 2 H18F H 0.5240 0.0194 0.9637 0.120 Uiso 0.455(13) 1 calc PR A 2 N1 N 0.65483(12) -0.05110(14) 0.73271(7) 0.0438(4) Uani 1 1 d . . . H1A H 0.6239 0.0123 0.7187 0.053 Uiso 1 1 calc R . . H1B H 0.6051 -0.0913 0.7504 0.053 Uiso 1 1 calc R . . C19 C 0.73261(19) -0.0148(2) 0.76953(9) 0.0682(7) Uani 1 1 d . . . H19A H 0.7643 -0.0817 0.7858 0.102 Uiso 1 1 calc R . . H19B H 0.7007 0.0326 0.7965 0.102 Uiso 1 1 calc R . . H19C H 0.7855 0.0293 0.7512 0.102 Uiso 1 1 calc R . . C20 C 0.69418(16) -0.12206(19) 0.68983(8) 0.0479(5) Uani 1 1 d . . . H20A H 0.7491 -0.0812 0.6715 0.072 Uiso 1 1 calc R . . H20B H 0.6381 -0.1389 0.6654 0.072 Uiso 1 1 calc R . . H20C H 0.7215 -0.1933 0.7040 0.072 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 0.0341(11) 0.0307(11) 0.0288(11) -0.0023(8) -0.0019(8) 0.0036(9) O1 0.0279(6) 0.0376(7) 0.0267(6) -0.0044(5) -0.0047(5) 0.0048(5) O2 0.0305(6) 0.0452(8) 0.0306(7) -0.0039(6) 0.0002(5) 0.0074(6) C1 0.0278(8) 0.0223(8) 0.0274(8) 0.0005(7) -0.0048(7) 0.0002(7) C2 0.0328(9) 0.0225(9) 0.0295(9) 0.0005(7) -0.0025(7) -0.0013(7) C3 0.0401(10) 0.0361(10) 0.0291(9) -0.0016(8) -0.0061(8) -0.0009(8) C4 0.0372(10) 0.0407(11) 0.0380(11) 0.0007(9) -0.0133(8) 0.0009(9) C5 0.0296(9) 0.0342(10) 0.0421(10) 0.0015(8) -0.0048(8) 0.0024(8) C6 0.0308(9) 0.0255(9) 0.0306(9) 0.0004(7) -0.0010(7) 0.0017(7) C7 0.0342(9) 0.0302(9) 0.0281(9) 0.0002(7) -0.0002(7) 0.0017(8) C8 0.0449(11) 0.0416(11) 0.0437(11) -0.0097(9) 0.0000(9) 0.0063(9) C9 0.0416(12) 0.0434(13) 0.0767(16) 0.0077(11) 0.0134(11) -0.0020(10) O3 0.0396(7) 0.0247(6) 0.0280(6) -0.0041(5) -0.0049(5) -0.0005(5) O4 0.0453(7) 0.0256(6) 0.0294(7) 0.0005(5) -0.0007(5) 0.0023(5) C10 0.0250(8) 0.0265(9) 0.0288(9) -0.0059(7) -0.0002(7) 0.0007(7) C11 0.0266(9) 0.0312(10) 0.0301(9) -0.0016(8) 0.0017(7) 0.0001(7) C12 0.0388(10) 0.0418(11) 0.0275(9) -0.0038(8) -0.0004(8) -0.0003(8) C13 0.0424(11) 0.0394(11) 0.0351(10) -0.0136(9) 0.0007(8) -0.0020(9) C14 0.0376(10) 0.0259(9) 0.0413(11) -0.0084(8) 0.0027(8) -0.0016(8) C15 0.0280(8) 0.0263(9) 0.0295(9) -0.0015(7) 0.0013(7) 0.0022(7) C16 0.0443(11) 0.0321(10) 0.0373(10) 0.0038(8) 0.0069(8) 0.0004(8) C17A 0.056(3) 0.052(3) 0.097(7) 0.017(3) 0.012(3) -0.017(2) C18A 0.069(4) 0.037(3) 0.075(4) 0.012(3) -0.015(3) 0.007(3) C17B 0.048(3) 0.041(3) 0.083(6) 0.008(3) 0.010(3) -0.016(2) C18B 0.127(10) 0.057(4) 0.056(4) 0.018(3) -0.019(5) 0.004(6) N1 0.0353(9) 0.0355(9) 0.0605(11) -0.0045(8) 0.0101(8) -0.0010(7) C19 0.0517(14) 0.0893(19) 0.0636(14) -0.0222(14) -0.0187(12) 0.0287(14) C20 0.0474(12) 0.0526(13) 0.0435(11) 0.0017(10) 0.0098(9) 0.0002(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 B1 O3 1.473(2) . ? B1 O4 1.483(2) . ? B1 O2 1.486(2) . ? B1 O1 1.489(2) . ? O1 C1 1.3766(19) . ? O2 C6 1.365(2) . ? C1 C2 1.380(2) . ? C1 C6 1.397(2) . ? C2 C3 1.406(2) . ? C2 C7 1.520(2) . ? C3 C4 1.382(3) . ? C4 C5 1.396(3) . ? C5 C6 1.374(2) . ? C7 C8 1.524(3) . ? C7 C9 1.525(3) . ? O3 C10 1.375(2) . ? O4 C15 1.370(2) . ? C10 C11 1.375(2) . ? C10 C15 1.395(3) . ? C11 C12 1.405(3) . ? C11 C16 1.517(3) . ? C12 C13 1.383(3) . ? C13 C14 1.394(3) . ? C14 C15 1.373(2) . ? C16 C18B 1.460(8) . ? C16 C17A 1.498(6) . ? C16 C17B 1.566(7) . ? C16 C18A 1.567(7) . ? N1 C19 1.447(3) . ? N1 C20 1.471(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 O3 B1 O4 105.32(13) . . ? O3 B1 O2 113.38(15) . . ? O4 B1 O2 109.18(15) . . ? O3 B1 O1 110.12(15) . . ? O4 B1 O1 114.24(15) . . ? O2 B1 O1 104.81(13) . . ? C1 O1 B1 106.93(13) . . ? C6 O2 B1 107.19(13) . . ? O1 C1 C2 127.11(15) . . ? O1 C1 C6 110.19(14) . . ? C2 C1 C6 122.68(15) . . ? C1 C2 C3 115.40(16) . . ? C1 C2 C7 122.07(15) . . ? C3 C2 C7 122.53(16) . . ? C4 C3 C2 122.05(17) . . ? C3 C4 C5 121.62(17) . . ? C6 C5 C4 116.73(17) . . ? O2 C6 C5 127.66(16) . . ? O2 C6 C1 110.82(14) . . ? C5 C6 C1 121.51(16) . . ? C2 C7 C8 112.12(15) . . ? C2 C7 C9 111.23(15) . . ? C8 C7 C9 110.99(16) . . ? C10 O3 B1 107.08(13) . . ? C15 O4 B1 106.57(13) . . ? O3 C10 C11 127.34(16) . . ? O3 C10 C15 110.02(15) . . ? C11 C10 C15 122.65(16) . . ? C10 C11 C12 115.46(17) . . ? C10 C11 C16 121.59(16) . . ? C12 C11 C16 122.94(17) . . ? C13 C12 C11 122.09(18) . . ? C12 C13 C14 121.42(17) . . ? C15 C14 C13 116.80(17) . . ? O4 C15 C14 127.70(16) . . ? O4 C15 C10 110.73(15) . . ? C14 C15 C10 121.53(16) . . ? C18B C16 C17A 79.5(5) . . ? C18B C16 C11 117.0(4) . . ? C17A C16 C11 111.3(3) . . ? C18B C16 C17B 111.5(5) . . ? C17A C16 C17B 36.1(3) . . ? C11 C16 C17B 108.3(3) . . ? C18B C16 C18A 30.1(4) . . ? C17A C16 C18A 108.9(4) . . ? C11 C16 C18A 109.7(3) . . ? C17B C16 C18A 136.7(4) . . ? C19 N1 C20 114.33(17) . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 64.54 _diffrn_measured_fraction_theta_full 0.962 _refine_diff_density_max 0.212 _refine_diff_density_min -0.278 _refine_diff_density_rms 0.045