# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2009 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Xiaodong Shi' _publ_contact_author_email XIAODONG.SHI@MAIL.WVU.EDU _publ_section_title ; 1,2,3-Triazole-Boranes: Stable and Efficient Reagents for Ketone and Aldehyde Reductive Amination in Organic Solvents or in Water ; loop_ _publ_author_name 'Xiaodong Shi.' 'Yunfeng Chen.' 'Haifeng Duan.' 'Wenyan Liao.' 'Yu-Xiu Liu.' ; J.L.Petersen ; # Attachment '2a.cif' data_ms77alt _database_code_depnum_ccdc_archive 'CCDC 741401' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H10 B N3' _chemical_formula_weight 146.99 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 triclinic _symmetry_space_group_name_H-M P_-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.1841(7) _cell_length_b 8.4683(7) _cell_length_c 12.0614(10) _cell_angle_alpha 92.839(2) _cell_angle_beta 103.1050(10) _cell_angle_gamma 94.8700(10) _cell_volume 809.17(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3490 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 27.46 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.207 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9677 _exptl_absorpt_correction_T_max 0.9763 _exptl_absorpt_process_details SADABS _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5506 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.57 _diffrn_reflns_theta_max 27.55 _reflns_number_total 3518 _reflns_number_gt 2661 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1140P)^2^+0.0584P] 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 SHELXL _refine_ls_extinction_coef 0.008(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3518 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0637 _refine_ls_wR_factor_ref 0.1984 _refine_ls_wR_factor_gt 0.1812 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 N1 N 0.32245(16) 0.27772(15) 1.00618(10) 0.0442(3) Uani 1 1 d . . . N2 N 0.46696(17) 0.21828(15) 1.01318(10) 0.0468(3) Uani 1 1 d . . . N3 N 0.52978(16) 0.26961(15) 0.92789(10) 0.0444(3) Uani 1 1 d . . . N4 N 1.06467(15) 0.77902(15) 0.42156(10) 0.0433(3) Uani 1 1 d . . . N5 N 0.99724(16) 0.72277(15) 0.50217(10) 0.0461(3) Uani 1 1 d . . . N6 N 0.84671(16) 0.77677(15) 0.48971(10) 0.0440(3) Uani 1 1 d . . . C1 C 0.29027(18) 0.36956(16) 0.91436(12) 0.0416(4) Uani 1 1 d . . . C2 C 0.42566(19) 0.36517(16) 0.86306(11) 0.0416(4) Uani 1 1 d . . . C3 C 0.4343(2) 0.44607(19) 0.76576(13) 0.0553(4) Uani 1 1 d . . . H3 H 0.5257 0.4438 0.7320 0.066 Uiso 1 1 calc R . . C4 C 0.2997(3) 0.5289(2) 0.72339(15) 0.0647(5) Uani 1 1 d . . . H4 H 0.2997 0.5845 0.6588 0.078 Uiso 1 1 calc R . . C5 C 0.1612(3) 0.5324(2) 0.77452(16) 0.0643(5) Uani 1 1 d . . . H5 H 0.0726 0.5900 0.7424 0.077 Uiso 1 1 calc R . . C6 C 0.1529(2) 0.45386(19) 0.86981(14) 0.0551(4) Uani 1 1 d . . . H6 H 0.0612 0.4563 0.9032 0.066 Uiso 1 1 calc R . . C7 C 0.6896(2) 0.2196(2) 0.91184(15) 0.0623(5) Uani 1 1 d . . . H7A H 0.7809 0.2787 0.9662 0.093 Uiso 1 1 calc R . . H7B H 0.7004 0.2389 0.8359 0.093 Uiso 1 1 calc R . . H7C H 0.6925 0.1083 0.9228 0.093 Uiso 1 1 calc R . . C8 C 0.95679(19) 0.87128(17) 0.35515(11) 0.0408(4) Uani 1 1 d . . . C9 C 0.81462(18) 0.87077(17) 0.39954(11) 0.0416(4) Uani 1 1 d . . . C10 C 0.6768(2) 0.95364(19) 0.35254(14) 0.0539(4) Uani 1 1 d . . . H10 H 0.5817 0.9533 0.3826 0.065 Uiso 1 1 calc R . . C11 C 0.6919(3) 1.0352(2) 0.25930(16) 0.0638(5) Uani 1 1 d . . . H11 H 0.6042 1.0926 0.2252 0.077 Uiso 1 1 calc R . . C12 C 0.8354(3) 1.0351(2) 0.21344(14) 0.0630(5) Uani 1 1 d . . . H12 H 0.8388 1.0917 0.1497 0.076 Uiso 1 1 calc R . . C13 C 0.9701(2) 0.9548(2) 0.25904(13) 0.0553(4) Uani 1 1 d . . . H13 H 1.0647 0.9553 0.2284 0.066 Uiso 1 1 calc R . . C14 C 0.7379(2) 0.7323(2) 0.56594(15) 0.0631(5) Uani 1 1 d . . . H14A H 0.7545 0.8126 0.6276 0.095 Uiso 0.58(2) 1 calc PR A 1 H14B H 0.7653 0.6326 0.5961 0.095 Uiso 0.58(2) 1 calc PR A 1 H14C H 0.6222 0.7226 0.5244 0.095 Uiso 0.58(2) 1 calc PR A 1 H14D H 0.6696 0.8168 0.5745 0.095 Uiso 0.42(2) 1 d PR A 2 H14E H 0.8060 0.7135 0.6391 0.095 Uiso 0.42(2) 1 d PR A 2 H14F H 0.6665 0.6375 0.5343 0.095 Uiso 0.42(2) 1 d PR A 2 B1 B 0.2086(3) 0.2419(3) 1.09348(18) 0.0626(5) Uani 1 1 d . . . H1A H 0.2689 0.1854 1.1543 0.094 Uiso 1 1 calc R . . H1B H 0.1069 0.1785 1.0549 0.094 Uiso 1 1 calc R . . H1C H 0.1809 0.3402 1.1243 0.094 Uiso 1 1 calc R . . B2 B 1.2438(3) 0.7397(3) 0.40635(17) 0.0603(5) Uani 1 1 d . . . H2A H 1.2308 0.6723 0.3379 0.091 Uiso 0.72(3) 1 calc PR B 1 H2B H 1.2988 0.6864 0.4708 0.091 Uiso 0.72(3) 1 calc PR B 1 H2C H 1.3107 0.8366 0.4010 0.091 Uiso 0.72(3) 1 calc PR B 1 H2D H 1.2389 0.6295 0.3817 0.091 Uiso 0.28(3) 1 d PR B 2 H2E H 1.3248 0.7616 0.4778 0.091 Uiso 0.28(3) 1 d PR B 2 H2F H 1.2765 0.8042 0.3503 0.091 Uiso 0.28(3) 1 d PR B 2 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 N1 0.0454(7) 0.0465(7) 0.0433(6) 0.0052(5) 0.0139(5) 0.0080(5) N2 0.0487(7) 0.0544(7) 0.0401(6) 0.0081(5) 0.0119(5) 0.0147(6) N3 0.0430(7) 0.0538(7) 0.0391(6) 0.0063(5) 0.0118(5) 0.0125(5) N4 0.0399(7) 0.0500(7) 0.0415(6) 0.0075(5) 0.0115(5) 0.0054(5) N5 0.0415(7) 0.0548(7) 0.0437(6) 0.0103(5) 0.0110(5) 0.0067(5) N6 0.0387(6) 0.0518(7) 0.0435(6) 0.0093(5) 0.0122(5) 0.0048(5) C1 0.0428(8) 0.0388(7) 0.0417(7) 0.0017(5) 0.0060(6) 0.0061(6) C2 0.0445(8) 0.0413(7) 0.0377(7) 0.0022(5) 0.0063(5) 0.0055(6) C3 0.0689(11) 0.0516(9) 0.0451(8) 0.0082(6) 0.0134(7) 0.0015(8) C4 0.0885(14) 0.0496(9) 0.0505(9) 0.0145(7) 0.0022(9) 0.0072(9) C5 0.0673(12) 0.0499(9) 0.0671(11) 0.0093(8) -0.0072(9) 0.0169(8) C6 0.0481(9) 0.0492(9) 0.0653(10) 0.0016(7) 0.0054(7) 0.0126(7) C7 0.0522(10) 0.0838(12) 0.0586(9) 0.0101(8) 0.0205(7) 0.0263(9) C8 0.0433(8) 0.0410(7) 0.0375(7) 0.0045(5) 0.0087(5) 0.0023(6) C9 0.0405(8) 0.0413(7) 0.0415(7) 0.0025(5) 0.0078(6) 0.0013(6) C10 0.0445(9) 0.0501(9) 0.0635(10) 0.0025(7) 0.0039(7) 0.0088(7) C11 0.0671(12) 0.0513(9) 0.0637(10) 0.0105(7) -0.0078(9) 0.0114(8) C12 0.0825(13) 0.0523(9) 0.0495(9) 0.0173(7) 0.0037(8) 0.0039(9) C13 0.0676(11) 0.0549(9) 0.0449(8) 0.0100(6) 0.0171(7) 0.0007(8) C14 0.0550(10) 0.0778(12) 0.0648(10) 0.0202(8) 0.0289(8) 0.0045(9) B1 0.0603(12) 0.0746(13) 0.0626(11) 0.0138(9) 0.0312(9) 0.0109(10) B2 0.0479(10) 0.0767(13) 0.0639(11) 0.0144(9) 0.0232(8) 0.0150(9) _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 N1 N2 1.3112(18) . ? N1 C1 1.3743(18) . ? N1 B1 1.580(2) . ? N2 N3 1.3258(18) . ? N3 C2 1.3675(19) . ? N3 C7 1.459(2) . ? N4 N5 1.3120(18) . ? N4 C8 1.3747(19) . ? N4 B2 1.578(2) . ? N5 N6 1.3297(18) . ? N6 C9 1.3700(19) . ? N6 C14 1.459(2) . ? C1 C2 1.388(2) . ? C1 C6 1.401(2) . ? C2 C3 1.400(2) . ? C3 C4 1.371(3) . ? C4 C5 1.409(3) . ? C5 C6 1.368(3) . ? C8 C9 1.387(2) . ? C8 C13 1.408(2) . ? C9 C10 1.404(2) . ? C10 C11 1.372(3) . ? C11 C12 1.408(3) . ? C12 C13 1.367(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 N2 N1 C1 109.94(12) . . ? N2 N1 B1 122.28(14) . . ? C1 N1 B1 127.78(14) . . ? N1 N2 N3 107.38(12) . . ? N2 N3 C2 111.51(13) . . ? N2 N3 C7 120.03(13) . . ? C2 N3 C7 128.45(14) . . ? N5 N4 C8 110.27(13) . . ? N5 N4 B2 122.72(14) . . ? C8 N4 B2 127.00(14) . . ? N4 N5 N6 107.16(12) . . ? N5 N6 C9 111.32(12) . . ? N5 N6 C14 120.51(14) . . ? C9 N6 C14 128.16(14) . . ? N1 C1 C2 106.87(13) . . ? N1 C1 C6 131.75(15) . . ? C2 C1 C6 121.37(15) . . ? N3 C2 C1 104.30(13) . . ? N3 C2 C3 133.41(16) . . ? C1 C2 C3 122.29(15) . . ? C4 C3 C2 115.79(18) . . ? C3 C4 C5 122.11(18) . . ? C6 C5 C4 122.14(16) . . ? C5 C6 C1 116.30(17) . . ? N4 C8 C9 106.67(13) . . ? N4 C8 C13 131.86(15) . . ? C9 C8 C13 121.46(15) . . ? N6 C9 C8 104.57(13) . . ? N6 C9 C10 133.00(15) . . ? C8 C9 C10 122.43(15) . . ? C11 C10 C9 115.49(17) . . ? C10 C11 C12 122.27(17) . . ? C13 C12 C11 122.46(17) . . ? C12 C13 C8 115.89(17) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.254 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.051