# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 222 loop_ _publ_author_name _publ_author_address 'Aaron Sadow' ; 1605 Gilman Hall, Iowa State University, Ames, Iowa, 50011, USA ; 'James F. Dunne' ; 1711 Gilman Hall, Iowa State University, Ames, Iowa, 50011, USA ; 'Arkady Ellern' ; 1605 Gilman Hall, Iowa State University, Ames, Iowa, 50011, USA ; 'Kuntal Manna' ; 1605 Gilman Hall, Iowa State University, Ames, Iowa, 50011, USA ; 'Marek Pruski' ; 1605 Gilman Hall, Iowa State University, Ames, Iowa, 50011, USA ; 'Jerzy W. Wiench' ; 1605 Gilman Hall, Iowa State University, Ames, Iowa, 50011, USA ; _publ_contact_author_name 'Aaron Sadow' _publ_contact_author_email SADOW@IASTATE.EDU _publ_section_title ; Bis(oxazolinyl)phenylborane: A Lewis Acid-containing Ligand for Aluminum(III), Methide Abstraction-based Coordination, and Comparisons with Tris(oxazolinyl)boratoaluminum Catalyzed Lactide Ring Opening Polymerization ; _publ_contact_author_address ;1605 Gilman Hall Department of Chemistry Iowa State University Ames, IA 50011 ; _publ_contact_author_fax +1-515-294-0105 _publ_contact_author_phone +1-515-294-8069 _publ_contact_letter ; This X-Ray structure Determination has been done in Molecular Structure Lab of Chemistry Department of Iowa State University by Dr. Arkady Ellern. #=================================================================== ; _publ_requested_journal D # Attachment 'PhBOx21.cif' data_sad21 _database_code_depnum_ccdc_archive 'CCDC 736433' _vrf_PLAT027_sad21 ; PROBLEM: _diffrn_reflns_theta_full (too) Low ............ 23.36 Deg. RESPONSE: No reasonabler high resolution data because of non-merohedral twinning. ; _vrf_PLAT029_sad21 ; PROBLEM: _diffrn_measured_fraction_theta_full Low ....... 0.93 RESPONSE: No reasonabler high resolution data because of non-merohedral twinning. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H30 Al B N2 O2' _chemical_formula_weight 356.24 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Al Al 0.0645 0.0514 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 6.942(7) _cell_length_b 22.74(2) _cell_length_c 13.445(13) _cell_angle_alpha 90.00 _cell_angle_beta 98.61(2) _cell_angle_gamma 90.00 _cell_volume 2099(3) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 819 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 23.21 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.127 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9573 _exptl_absorpt_correction_T_max 0.9678 _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13278 _diffrn_reflns_av_R_equivalents 0.1564 _diffrn_reflns_av_sigmaI/netI 0.0835 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 23.36 _reflns_number_total 2823 _reflns_number_gt 1886 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0942P)^2^+6.4258P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2823 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1355 _refine_ls_R_factor_gt 0.0900 _refine_ls_wR_factor_ref 0.2605 _refine_ls_wR_factor_gt 0.2220 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_restrained_S_all 1.144 _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 Al1 Al 0.2545(3) 0.67091(7) 0.24706(13) 0.0325(6) Uani 1 1 d . . . B1 B 0.1087(10) 0.5279(3) 0.2913(5) 0.0307(16) Uani 1 1 d . . . C1 C 0.0092(9) 0.6264(3) 0.0517(4) 0.0348(15) Uani 1 1 d . . . C2 C -0.0757(10) 0.6869(3) 0.0326(5) 0.0419(17) Uani 1 1 d . . . H2A H -0.1782 0.6930 0.0743 0.063 Uiso 1 1 calc R . . H2B H -0.1311 0.6906 -0.0386 0.063 Uiso 1 1 calc R . . H2C H 0.0269 0.7164 0.0495 0.063 Uiso 1 1 calc R . . C3 C 0.1733(10) 0.6146(3) -0.0109(5) 0.053(2) Uani 1 1 d . . . H3A H 0.2787 0.6431 0.0074 0.080 Uiso 1 1 calc R . . H3B H 0.1222 0.6186 -0.0826 0.080 Uiso 1 1 calc R . . H3C H 0.2236 0.5747 0.0026 0.080 Uiso 1 1 calc R . . C4 C -0.1443(10) 0.5780(3) 0.0350(4) 0.0407(16) Uani 1 1 d . . . H4A H -0.2760 0.5940 0.0377 0.049 Uiso 1 1 calc R . . H4B H -0.1436 0.5585 -0.0308 0.049 Uiso 1 1 calc R . . C5 C 0.0405(8) 0.5649(3) 0.1890(4) 0.0296(14) Uani 1 1 d . . . C6 C 0.2256(8) 0.4711(2) 0.2585(4) 0.0297(15) Uani 1 1 d . . . C7 C 0.3971(9) 0.4786(3) 0.2181(4) 0.0370(16) Uani 1 1 d . . . H7 H 0.4411 0.5175 0.2094 0.044 Uiso 1 1 calc R . . C8 C 0.5085(10) 0.4322(3) 0.1894(5) 0.053(2) Uani 1 1 d . . . H8 H 0.6244 0.4394 0.1618 0.063 Uiso 1 1 calc R . . C9 C 0.4455(12) 0.3754(4) 0.2023(5) 0.061(2) Uani 1 1 d . . . H9 H 0.5193 0.3430 0.1840 0.073 Uiso 1 1 calc R . . C10 C 0.2782(13) 0.3656(3) 0.2410(5) 0.058(2) Uani 1 1 d . . . H10 H 0.2349 0.3265 0.2487 0.069 Uiso 1 1 calc R . . C11 C 0.1681(10) 0.4133(3) 0.2700(4) 0.0411(17) Uani 1 1 d . . . H11 H 0.0527 0.4056 0.2979 0.049 Uiso 1 1 calc R . . C12 C -0.0808(9) 0.5133(3) 0.3448(4) 0.0456(17) Uani 1 1 d . . . H12A H -0.0410 0.4897 0.4055 0.068 Uiso 1 1 calc R . . H12B H -0.1760 0.4912 0.2980 0.068 Uiso 1 1 calc R . . H12C H -0.1398 0.5501 0.3632 0.068 Uiso 1 1 calc R . . C13 C 0.2536(8) 0.5677(3) 0.3686(4) 0.0306(14) Uani 1 1 d . . . C14 C 0.4630(10) 0.5802(3) 0.5146(4) 0.0436(18) Uani 1 1 d . . . H14A H 0.5987 0.5692 0.5085 0.052 Uiso 1 1 calc R . . H14B H 0.4471 0.5801 0.5866 0.052 Uiso 1 1 calc R . . C15 C 0.4106(9) 0.6402(3) 0.4667(4) 0.0388(16) Uani 1 1 d . . . C16 C 0.2662(13) 0.6717(4) 0.5227(5) 0.070(3) Uani 1 1 d . . . H16A H 0.3311 0.6830 0.5897 0.106 Uiso 1 1 calc R . . H16B H 0.1571 0.6453 0.5293 0.106 Uiso 1 1 calc R . . H16C H 0.2172 0.7069 0.4852 0.106 Uiso 1 1 calc R . . C17 C 0.5869(11) 0.6772(3) 0.4606(6) 0.065(2) Uani 1 1 d . . . H17A H 0.6710 0.6573 0.4188 0.097 Uiso 1 1 calc R . . H17B H 0.6587 0.6832 0.5283 0.097 Uiso 1 1 calc R . . H17C H 0.5463 0.7154 0.4307 0.097 Uiso 1 1 calc R . . C18 C 0.1028(11) 0.7412(3) 0.2765(5) 0.0527(19) Uani 1 1 d . . . H18A H -0.0196 0.7286 0.2980 0.079 Uiso 1 1 calc R . . H18B H 0.0742 0.7654 0.2158 0.079 Uiso 1 1 calc R . . H18C H 0.1788 0.7642 0.3303 0.079 Uiso 1 1 calc R . . C19 C 0.4937(11) 0.6852(3) 0.1940(5) 0.058(2) Uani 1 1 d . . . H19A H 0.5751 0.7126 0.2382 0.087 Uiso 1 1 calc R . . H19B H 0.4637 0.7023 0.1265 0.087 Uiso 1 1 calc R . . H19C H 0.5637 0.6481 0.1904 0.087 Uiso 1 1 calc R . . N1 N 0.0917(7) 0.6169(2) 0.1613(3) 0.0289(11) Uani 1 1 d . . . N2 N 0.3062(7) 0.6223(2) 0.3647(3) 0.0292(12) Uani 1 1 d . . . O1 O -0.0858(6) 0.53672(18) 0.1182(3) 0.0408(12) Uani 1 1 d . . . O2 O 0.3234(6) 0.54049(17) 0.4562(3) 0.0384(11) 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 Al1 0.0359(11) 0.0329(10) 0.0282(10) -0.0003(8) 0.0035(8) -0.0016(8) B1 0.030(4) 0.041(4) 0.020(3) 0.000(3) -0.002(3) -0.002(3) C1 0.034(4) 0.045(4) 0.023(3) 0.005(3) -0.001(3) 0.003(3) C2 0.046(4) 0.045(4) 0.032(3) 0.008(3) -0.002(3) -0.001(3) C3 0.053(5) 0.084(5) 0.024(3) 0.002(3) 0.010(3) 0.017(4) C4 0.048(4) 0.045(4) 0.024(3) 0.001(3) -0.009(3) 0.006(3) C5 0.028(3) 0.037(3) 0.022(3) -0.004(3) 0.001(3) 0.003(3) C6 0.033(4) 0.038(3) 0.014(3) -0.003(2) -0.007(3) -0.006(3) C7 0.039(4) 0.049(4) 0.021(3) -0.008(3) -0.001(3) 0.000(3) C8 0.047(4) 0.067(5) 0.040(4) -0.024(4) -0.010(3) 0.007(4) C9 0.062(5) 0.062(5) 0.048(4) -0.025(4) -0.024(4) 0.018(4) C10 0.082(6) 0.041(4) 0.043(4) -0.011(3) -0.018(4) -0.005(4) C11 0.046(4) 0.040(4) 0.033(3) -0.003(3) -0.008(3) -0.006(3) C12 0.041(4) 0.068(5) 0.026(3) 0.002(3) 0.001(3) -0.011(3) C13 0.035(3) 0.038(4) 0.019(3) 0.002(3) 0.004(3) 0.008(3) C14 0.052(4) 0.046(4) 0.027(3) -0.012(3) -0.012(3) -0.006(3) C15 0.041(4) 0.040(4) 0.030(3) -0.009(3) -0.011(3) -0.003(3) C16 0.095(6) 0.079(6) 0.032(4) -0.023(4) -0.007(4) 0.037(5) C17 0.066(5) 0.070(5) 0.050(4) -0.002(4) -0.016(4) -0.021(4) C18 0.069(5) 0.042(4) 0.043(4) -0.005(3) -0.004(4) 0.008(3) C19 0.066(5) 0.058(5) 0.049(4) 0.000(4) 0.006(4) -0.009(4) N1 0.034(3) 0.038(3) 0.016(2) 0.004(2) 0.007(2) 0.003(2) N2 0.031(3) 0.035(3) 0.022(2) -0.009(2) 0.003(2) -0.001(2) O1 0.052(3) 0.043(2) 0.021(2) -0.0002(18) -0.0168(19) -0.005(2) O2 0.054(3) 0.037(2) 0.020(2) -0.0006(17) -0.0095(19) -0.0050(19) _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 Al1 N2 1.918(5) . ? Al1 N1 1.931(5) . ? Al1 C19 1.931(8) . ? Al1 C18 1.986(7) . ? B1 C13 1.612(8) . ? B1 C6 1.621(9) . ? B1 C5 1.622(8) . ? B1 C12 1.625(10) . ? C1 C2 1.502(9) . ? C1 N1 1.514(7) . ? C1 C4 1.526(9) . ? C1 C3 1.538(9) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C4 O1 1.470(7) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N1 1.305(7) . ? C5 O1 1.355(6) . ? C6 C11 1.391(8) . ? C6 C7 1.391(9) . ? C7 C8 1.396(9) . ? C7 H7 0.9500 . ? C8 C9 1.382(11) . ? C8 H8 0.9500 . ? C9 C10 1.360(11) . ? C9 H9 0.9500 . ? C10 C11 1.413(10) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N2 1.298(7) . ? C13 O2 1.354(6) . ? C14 O2 1.465(7) . ? C14 C15 1.530(9) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C17 1.497(10) . ? C15 N2 1.508(7) . ? C15 C16 1.520(10) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? 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 Al1 N1 98.4(2) . . ? N2 Al1 C19 109.7(3) . . ? N1 Al1 C19 110.2(3) . . ? N2 Al1 C18 109.8(3) . . ? N1 Al1 C18 110.5(3) . . ? C19 Al1 C18 116.7(3) . . ? C13 B1 C6 109.5(5) . . ? C13 B1 C5 109.3(5) . . ? C6 B1 C5 106.1(5) . . ? C13 B1 C12 107.3(5) . . ? C6 B1 C12 115.4(5) . . ? C5 B1 C12 109.2(5) . . ? C2 C1 N1 112.3(5) . . ? C2 C1 C4 112.9(5) . . ? N1 C1 C4 101.2(4) . . ? C2 C1 C3 111.7(5) . . ? N1 C1 C3 107.7(5) . . ? C4 C1 C3 110.6(5) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C1 C3 H3A 109.5 . . ? C1 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C1 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? O1 C4 C1 104.0(4) . . ? O1 C4 H4A 111.0 . . ? C1 C4 H4A 111.0 . . ? O1 C4 H4B 111.0 . . ? C1 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? N1 C5 O1 113.8(5) . . ? N1 C5 B1 130.9(5) . . ? O1 C5 B1 115.2(5) . . ? C11 C6 C7 115.8(6) . . ? C11 C6 B1 124.0(6) . . ? C7 C6 B1 120.2(5) . . ? C6 C7 C8 123.9(6) . . ? C6 C7 H7 118.0 . . ? C8 C7 H7 118.0 . . ? C9 C8 C7 118.2(7) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C10 C9 C8 120.3(7) . . ? C10 C9 H9 119.9 . . ? C8 C9 H9 119.9 . . ? C9 C10 C11 120.6(7) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C6 C11 C10 121.3(7) . . ? C6 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? B1 C12 H12A 109.5 . . ? B1 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? B1 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N2 C13 O2 114.0(5) . . ? N2 C13 B1 131.6(5) . . ? O2 C13 B1 114.3(5) . . ? O2 C14 C15 103.2(4) . . ? O2 C14 H14A 111.1 . . ? C15 C14 H14A 111.1 . . ? O2 C14 H14B 111.1 . . ? C15 C14 H14B 111.1 . . ? H14A C14 H14B 109.1 . . ? C17 C15 N2 112.8(5) . . ? C17 C15 C16 111.6(6) . . ? N2 C15 C16 108.3(5) . . ? C17 C15 C14 112.3(5) . . ? N2 C15 C14 101.2(4) . . ? C16 C15 C14 110.1(6) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? Al1 C18 H18A 109.5 . . ? Al1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? Al1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? Al1 C19 H19A 109.5 . . ? Al1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? Al1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C5 N1 C1 109.2(4) . . ? C5 N1 Al1 124.5(4) . . ? C1 N1 Al1 126.3(4) . . ? C13 N2 C15 108.7(4) . . ? C13 N2 Al1 124.5(4) . . ? C15 N2 Al1 126.8(4) . . ? C5 O1 C4 108.0(4) . . ? C13 O2 C14 107.8(4) . . ? _diffrn_measured_fraction_theta_max 0.967 _diffrn_reflns_theta_full 23.36 _diffrn_measured_fraction_theta_full 0.967 _refine_diff_density_max 0.505 _refine_diff_density_min -0.346 _refine_diff_density_rms 0.085