Supplementary Material (ESI) for Chemical Communications This journal is (c) The Royal Society of Chemistry 2003 data_global _publ_contact_author_email CLYBURNE@SFU.CA _publ_contact_author_name 'Dr Jason A. C Clyburne' _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name J.A.C.Clyburne A.J.Jennings H.Jong I.D.McKenzie T.Ramnial data_02144b _database_code_CSD 203381 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H27 B N2' _chemical_formula_weight 318.26 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbcn loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y+1/2, z+1/2' '-x, y, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y-1/2, -z-1/2' 'x, -y, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 16.0680(3) _cell_length_b 7.24710(10) _cell_length_c 16.1949(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1885.84(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.73 _exptl_crystal_size_mid 0.53 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.121 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9544 _exptl_absorpt_correction_T_max 0.9822 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Nonius Kappa-CCD' _diffrn_measurement_method 'phi/omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21686 _diffrn_reflns_av_R_equivalents 0.052 _diffrn_reflns_av_sigmaI/netI 0.0338 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.82 _diffrn_reflns_theta_max 27.48 _reflns_number_total 2160 _reflns_number_gt 1554 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius COLLECT' _computing_cell_refinement 'Nonius DENZO' _computing_data_reduction 'Nonius DENZO' _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. ; _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^)+(0.1251P)^2^+0.5969P] 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 2160 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0682 _refine_ls_wR_factor_ref 0.2056 _refine_ls_wR_factor_gt 0.1896 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.002 _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 0.5000 0.4430(4) 0.7500 0.0341(7) Uani 1 2 d S . . H1A H 0.5219 0.4987 0.8170 0.051 Uiso 0.50 1 calc PR . . H1B H 0.4306 0.4987 0.7353 0.051 Uiso 0.50 1 calc PR . . H1C H 0.5476 0.4987 0.6977 0.051 Uiso 0.50 1 calc PR . . C2 C 0.5000 0.2228(3) 0.7500 0.0264(6) Uani 1 2 d S . . N3 N 0.46763(9) 0.1085(2) 0.69221(9) 0.0284(4) Uani 1 1 d . . . C4 C 0.47959(11) -0.0747(2) 0.71376(12) 0.0334(5) Uani 1 1 d . . . H4A H 0.4597 -0.1953 0.6787 0.050 Uiso 1 1 calc R . . C11 C 0.42546(11) 0.1675(2) 0.61808(11) 0.0259(4) Uani 1 1 d . . . C12 C 0.33833(11) 0.1610(3) 0.61674(12) 0.0319(5) Uani 1 1 d . . . C13 C 0.29897(12) 0.2136(3) 0.54415(12) 0.0354(5) Uani 1 1 d . . . H13A H 0.2400 0.2079 0.5413 0.042 Uiso 1 1 calc R . . C14 C 0.34291(11) 0.2740(2) 0.47570(12) 0.0307(5) Uani 1 1 d . . . C15 C 0.42947(11) 0.2807(2) 0.48049(12) 0.0277(4) Uani 1 1 d . . . H15A H 0.4600 0.3246 0.4343 0.033 Uiso 1 1 calc R . . C16 C 0.47234(11) 0.2255(2) 0.55054(11) 0.0256(4) Uani 1 1 d . . . C17 C 0.28957(13) 0.1021(4) 0.69162(13) 0.0469(6) Uani 1 1 d . . . H17A H 0.2299 0.1064 0.6791 0.070 Uiso 1 1 calc R . . H17B H 0.3018 0.1856 0.7376 0.070 Uiso 1 1 calc R . . H17C H 0.3053 -0.0241 0.7068 0.070 Uiso 1 1 calc R . . C18 C 0.29884(13) 0.3279(3) 0.39722(13) 0.0425(6) Uani 1 1 d . . . H18A H 0.3399 0.3659 0.3558 0.064 Uiso 1 1 calc R . . H18B H 0.2608 0.4306 0.4085 0.064 Uiso 1 1 calc R . . H18C H 0.2671 0.2223 0.3763 0.064 Uiso 1 1 calc R . . C19 C 0.56587(12) 0.2273(3) 0.55280(12) 0.0338(5) Uani 1 1 d . . . H19A H 0.5848 0.3083 0.5975 0.051 Uiso 1 1 calc R . . H19B H 0.5873 0.2729 0.5000 0.051 Uiso 1 1 calc R . . H19C H 0.5865 0.1019 0.5624 0.051 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 0.0521(18) 0.0212(13) 0.0290(17) 0.000 -0.0039(14) 0.000 C2 0.0305(12) 0.0253(12) 0.0234(13) 0.000 0.0004(10) 0.000 N3 0.0373(8) 0.0235(7) 0.0243(9) -0.0009(6) -0.0023(6) -0.0006(6) C4 0.0448(11) 0.0231(9) 0.0324(11) -0.0013(7) -0.0006(8) -0.0014(7) C11 0.0314(9) 0.0257(9) 0.0208(9) -0.0015(7) -0.0015(7) -0.0001(7) C12 0.0319(9) 0.0366(10) 0.0272(11) 0.0002(8) 0.0037(7) -0.0013(7) C13 0.0252(9) 0.0446(12) 0.0363(12) 0.0039(9) -0.0001(8) -0.0010(8) C14 0.0332(9) 0.0304(9) 0.0283(10) 0.0008(7) -0.0041(8) -0.0003(7) C15 0.0327(9) 0.0282(9) 0.0223(10) -0.0004(7) 0.0025(7) -0.0025(7) C16 0.0303(9) 0.0222(8) 0.0244(10) -0.0024(7) 0.0002(7) -0.0010(6) C17 0.0395(11) 0.0647(15) 0.0364(13) 0.0093(11) 0.0103(9) -0.0015(10) C18 0.0407(11) 0.0495(13) 0.0373(13) 0.0081(9) -0.0111(9) -0.0032(9) C19 0.0296(10) 0.0353(10) 0.0364(12) 0.0013(8) 0.0007(8) -0.0004(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 C2 1.596(4) . ? C2 N3 1.354(2) . ? C2 N3 1.354(2) 3_656 ? N3 C4 1.386(2) . ? N3 C11 1.444(2) . ? C4 C4 1.345(4) 3_656 ? C11 C16 1.393(2) . ? C11 C12 1.401(3) . ? C12 C13 1.388(3) . ? C12 C17 1.506(3) . ? C13 C14 1.385(3) . ? C14 C15 1.394(3) . ? C14 C18 1.507(3) . ? C15 C16 1.386(2) . ? C16 C19 1.503(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 N3 C2 N3 104.5(2) . 3_656 ? N3 C2 B1 127.75(10) . . ? N3 C2 B1 127.75(10) 3_656 . ? C2 N3 C4 111.04(16) . . ? C2 N3 C11 125.00(15) . . ? C4 N3 C11 123.96(15) . . ? C4 C4 N3 106.71(10) 3_656 . ? C16 C11 C12 122.58(17) . . ? C16 C11 N3 119.25(15) . . ? C12 C11 N3 118.16(15) . . ? C13 C12 C11 117.33(16) . . ? C13 C12 C17 121.52(17) . . ? C11 C12 C17 121.14(17) . . ? C14 C13 C12 122.15(18) . . ? C13 C14 C15 118.37(17) . . ? C13 C14 C18 121.17(17) . . ? C15 C14 C18 120.45(17) . . ? C16 C15 C14 122.10(16) . . ? C15 C16 C11 117.44(16) . . ? C15 C16 C19 120.95(16) . . ? C11 C16 C19 121.60(16) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.431 _refine_diff_density_min -0.262 _refine_diff_density_rms 0.063