# 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 #============================================================================ # 1. SUBMISSION DETAILS _publ_contact_author # Name and address of author for correspondence ; Holger F. Bettinger Institut f\"ur Organische Chemie Universit\"at T\"ubingen Auf der Morgenstelle 18 D-72076 T\"ubingen Bundesrepublik Deutschland ; _publ_contact_author_phone '049 7071 29 72072' _publ_contact_author_fax '049 7071 29 5244' _publ_contact_author_email holger.bettinger@uni-tuebingen.de #============================================================================ # 2. TITLE AND AUTHOR LIST _publ_section_title ; >From the Borole to the Azaborine Motife via a Formal Dyotropic Rearrangement ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Sunanda Biswas' ; Holger F. Betiinger Institut f\"ur Organische Chemie Universit\"at T\"ubingen Auf der Morgenstelle 18 D-72076 T\"ubingen ; C.Maichle-Mossmer ; Institut f\"ur Anorganische Chemie Universit\"at T\"ubingen Auf der Morgenstelle 18 D-72076 T\"ubingen ; H.F.Bettinger '' #+++++++++++++++++++++++++++++++++ data_orisb1b _database_code_depnum_ccdc_archive 'CCDC 845872' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 B N O Si' _chemical_formula_weight 267.20 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' N N 0.0061 0.0033 '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' Si Si 0.0817 0.0704 '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 P21/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 15.288(2) _cell_length_b 5.8962(5) _cell_length_c 16.276(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.042(11) _cell_angle_gamma 90.00 _cell_volume 1463.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 10757 _cell_measurement_theta_min 9.02 _cell_measurement_theta_max 59.10 _exptl_crystal_description coloumn _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.151 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'STOE IPDS II' _diffrn_measurement_method omega-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21898 _diffrn_reflns_av_R_equivalents 0.0898 _diffrn_reflns_av_sigmaI/netI 0.0379 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.67 _diffrn_reflns_theta_max 27.10 _reflns_number_total 3229 _reflns_number_gt 2701 _reflns_threshold_expression >2sigma(I) _computing_data_collection X-AREA _computing_cell_refinement X-AREA _computing_data_reduction X-AREA _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0324P)^2^+1.0559P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refU _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3229 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0751 _refine_ls_R_factor_gt 0.0597 _refine_ls_wR_factor_ref 0.1231 _refine_ls_wR_factor_gt 0.1169 _refine_ls_goodness_of_fit_ref 1.233 _refine_ls_restrained_S_all 1.233 _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 0.87824(18) -0.1882(4) 0.10725(18) 0.0371(6) Uani 1 1 d . . . C2 C 0.67933(16) -0.1376(4) 0.08045(16) 0.0330(5) Uani 1 1 d . . . C3 C 0.7860(2) 0.2202(4) 0.17670(17) 0.0373(6) Uani 1 1 d . . . C11 C 0.62028(14) 0.4846(4) -0.10278(13) 0.0280(5) Uani 1 1 d . . . C12 C 0.52845(15) 0.4777(5) -0.10844(15) 0.0352(5) Uani 1 1 d . . . C13 C 0.48056(16) 0.6446(5) -0.14956(16) 0.0392(6) Uani 1 1 d . . . C14 C 0.52294(16) 0.8227(5) -0.18610(16) 0.0373(6) Uani 1 1 d . . . C15 C 0.61354(16) 0.8281(4) -0.18204(14) 0.0319(5) Uani 1 1 d . . . C16 C 0.66502(14) 0.6611(4) -0.14052(12) 0.0250(4) Uani 1 1 d . . . C17 C 0.76204(13) 0.6649(4) -0.13605(12) 0.0240(4) Uani 1 1 d . . . C18 C 0.80869(15) 0.8348(4) -0.17504(14) 0.0305(5) Uani 1 1 d . . . C19 C 0.89954(16) 0.8352(4) -0.16973(15) 0.0343(5) Uani 1 1 d . . . C20 C 0.94635(15) 0.6669(5) -0.12607(15) 0.0342(5) Uani 1 1 d . . . C21 C 0.90180(14) 0.4987(5) -0.08788(13) 0.0308(5) Uani 1 1 d . . . C22 C 0.80944(13) 0.4939(4) -0.09153(12) 0.0249(4) Uani 1 1 d . . . H1 H 0.6364(18) 0.224(5) -0.0367(17) 0.039(8) Uiso 1 1 d . . . H1A H 0.933(2) -0.115(6) 0.103(2) 0.067(10) Uiso 1 1 d . . . H1B H 0.875(2) -0.303(6) 0.066(2) 0.067(10) Uiso 1 1 d . . . H2A H 0.629(2) -0.032(6) 0.0808(18) 0.057(9) Uiso 1 1 d . . . H2B H 0.673(2) -0.228(6) 0.030(2) 0.061(9) Uiso 1 1 d . . . H2C H 0.6751(19) -0.236(5) 0.127(2) 0.054(9) Uiso 1 1 d . . . H3A H 0.843(2) 0.287(6) 0.1873(19) 0.062(10) Uiso 1 1 d . . . H3B H 0.765(2) 0.155(6) 0.224(2) 0.067(10) Uiso 1 1 d . . . H3C H 0.745(2) 0.351(7) 0.162(2) 0.082(12) Uiso 1 1 d . . . H11C H 0.880(2) -0.259(7) 0.165(2) 0.087(12) Uiso 1 1 d . . . H12 H 0.5020(17) 0.353(5) -0.0812(16) 0.037(7) Uiso 1 1 d . . . H13 H 0.4176(17) 0.638(5) -0.1551(16) 0.039(7) Uiso 1 1 d . . . H14 H 0.4904(18) 0.939(5) -0.2175(17) 0.046(8) Uiso 1 1 d . . . H15 H 0.6405(16) 0.944(4) -0.2081(15) 0.032(7) Uiso 1 1 d . . . H18 H 0.7771(16) 0.947(4) -0.2072(15) 0.035(7) Uiso 1 1 d . . . H19 H 0.9280(18) 0.948(5) -0.1977(17) 0.045(8) Uiso 1 1 d . . . H20 H 1.0116(18) 0.668(5) -0.1249(17) 0.048(8) Uiso 1 1 d . . . H21 H 0.9315(17) 0.385(5) -0.0581(17) 0.041(7) Uiso 1 1 d . . . N1 N 0.66722(12) 0.3171(3) -0.05764(12) 0.0303(4) Uani 1 1 d . . . B1 B 0.76005(16) 0.3099(4) -0.04534(14) 0.0261(5) Uani 1 1 d . . . Si1 Si 0.78649(4) 0.01376(10) 0.08987(3) 0.02447(16) Uani 1 1 d . . . O1 O 0.80290(10) 0.1553(3) 0.00560(10) 0.0330(4) 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 0.0387(14) 0.0289(12) 0.0426(14) -0.0004(12) -0.0047(11) 0.0058(11) C2 0.0332(12) 0.0339(13) 0.0319(12) 0.0006(11) 0.0025(10) -0.0050(11) C3 0.0458(15) 0.0291(12) 0.0378(13) -0.0072(11) 0.0084(11) -0.0064(12) C11 0.0283(11) 0.0317(11) 0.0238(10) -0.0024(10) 0.0017(8) -0.0027(10) C12 0.0287(11) 0.0396(13) 0.0375(12) 0.0026(11) 0.0045(9) -0.0059(11) C13 0.0245(12) 0.0491(15) 0.0438(14) -0.0021(12) 0.0002(10) 0.0005(11) C14 0.0331(12) 0.0399(14) 0.0386(13) 0.0003(11) -0.0001(10) 0.0089(11) C15 0.0366(12) 0.0297(12) 0.0294(11) 0.0017(10) 0.0024(9) 0.0018(10) C16 0.0280(10) 0.0262(10) 0.0209(9) -0.0020(9) 0.0013(8) -0.0015(9) C17 0.0270(10) 0.0268(10) 0.0182(9) -0.0032(8) 0.0017(8) -0.0026(9) C18 0.0348(12) 0.0295(11) 0.0271(11) 0.0045(10) 0.0022(9) -0.0045(10) C19 0.0345(12) 0.0368(13) 0.0322(12) 0.0058(11) 0.0056(10) -0.0102(11) C20 0.0247(11) 0.0433(14) 0.0345(12) 0.0010(11) 0.0029(9) -0.0055(10) C21 0.0280(11) 0.0363(12) 0.0282(11) 0.0038(11) 0.0021(8) 0.0004(11) C22 0.0280(10) 0.0279(10) 0.0189(9) -0.0006(9) 0.0017(7) -0.0032(9) N1 0.0297(10) 0.0302(10) 0.0311(10) 0.0098(9) 0.0027(8) -0.0059(8) B1 0.0319(12) 0.0264(12) 0.0201(11) 0.0010(10) 0.0030(9) -0.0012(10) Si1 0.0286(3) 0.0208(3) 0.0240(3) 0.0015(2) 0.0018(2) -0.0007(3) O1 0.0325(8) 0.0346(9) 0.0323(8) 0.0111(7) 0.0050(7) 0.0032(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 C1 Si1 1.846(3) . ? C2 Si1 1.863(2) . ? C3 Si1 1.866(3) . ? C11 N1 1.399(3) . ? C11 C12 1.401(3) . ? C11 C16 1.409(3) . ? C12 C13 1.372(4) . ? C13 C14 1.390(4) . ? C14 C15 1.382(3) . ? C15 C16 1.404(3) . ? C16 C17 1.480(3) . ? C17 C18 1.407(3) . ? C17 C22 1.412(3) . ? C18 C19 1.386(3) . ? C19 C20 1.389(4) . ? C20 C21 1.376(3) . ? C21 C22 1.409(3) . ? C22 B1 1.547(3) . ? N1 B1 1.420(3) . ? B1 O1 1.368(3) . ? Si1 O1 1.6398(16) . ? 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 N1 C11 C12 119.2(2) . . ? N1 C11 C16 120.24(19) . . ? C12 C11 C16 120.5(2) . . ? C13 C12 C11 120.6(2) . . ? C12 C13 C14 120.1(2) . . ? C15 C14 C13 119.5(2) . . ? C14 C15 C16 122.2(2) . . ? C15 C16 C11 117.1(2) . . ? C15 C16 C17 122.6(2) . . ? C11 C16 C17 120.34(19) . . ? C18 C17 C22 118.82(19) . . ? C18 C17 C16 121.8(2) . . ? C22 C17 C16 119.39(19) . . ? C19 C18 C17 120.7(2) . . ? C18 C19 C20 120.6(2) . . ? C21 C20 C19 119.5(2) . . ? C20 C21 C22 121.4(2) . . ? C21 C22 C17 118.9(2) . . ? C21 C22 B1 121.0(2) . . ? C17 C22 B1 119.99(19) . . ? C11 N1 B1 124.5(2) . . ? O1 B1 N1 122.4(2) . . ? O1 B1 C22 122.2(2) . . ? N1 B1 C22 115.3(2) . . ? O1 Si1 C1 107.27(11) . . ? O1 Si1 C2 111.14(10) . . ? C1 Si1 C2 110.97(13) . . ? O1 Si1 C3 108.10(11) . . ? C1 Si1 C3 110.38(13) . . ? C2 Si1 C3 108.94(12) . . ? B1 O1 Si1 138.68(15) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.10 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.335 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.048