Borane as an efficient directing group. Stereoselective 1,2-addition of organometallic reagents to borane P-stereogenic N-phosphanylimines
Areli Flores-Gaspar; Silvia Orgue; Arnald Grabulosa; Antoni Riera; Xavier Verdaguer; Chem.Commun. 51 (2015) 1941–; doi:10.1039/C4cc09106J

data_7116448
_publ_section_title
;
 Borane as an efficient directing group. Stereoselective 1,2-addition of
 organometallic reagents to borane P-stereogenic N-phosphanylimines
;
_journal_name_full               Chem.Commun.
_journal_page_first              1941
_journal_paper_doi               10.1039/C4cc09106J
_journal_volume                  51
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_sum            'C12 H21 B N P'
_chemical_formula_weight         221.08
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2014-12-04 deposited with the CCDC.
2014-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.7930(18)
_cell_length_b                   11.0539(18)
_cell_length_c                   11.3385(18)
_cell_measurement_reflns_used    5724
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      34.29
_cell_measurement_theta_min      2.57
_cell_volume                     1352.7(4)
_computing_cell_refinement       'Bruker APEX2 v2011.4-0'
_computing_data_collection       'Bruker APEX2 v2011.4-0'
_computing_data_reduction        'Bruker SAINT V7.60A'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    Sir2011
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 512
_diffrn_detector_type            '4K CCD area detector APEX II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'APEX DUO Kappa 4-axis goniometer'
_diffrn_measurement_method
;
 Fullsphere data collection, phi and omega scans
;
_diffrn_measurement_specimen_support 'magnetic support with MicroMount'
_diffrn_radiation_monochromator  'Quazar MX Multilayer Optics'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.870
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         34.882
_diffrn_reflns_theta_min         2.573
_diffrn_source                   'Microfocus source E025 IuS'
_diffrn_source_current           0.6
_diffrn_source_power             50
_diffrn_source_size              '0.2 mm x 0.2 mm fine focus'
_diffrn_source_type              'Bruker APEX DUO'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  0.942
_exptl_absorpt_correction_T_min  0.854
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
; 
 SADABS Version 2008/1 Bruker-Nonius
 Blessing, Acta Cryst. (1995) A51 33-38
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.086
_exptl_crystal_description       block
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: hexanes-ethylacetate'
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.390
_refine_diff_density_rms         0.080
_refine_ls_abs_structure_details
;
 Flack x determined using 1736 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.863
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     141
_refine_ls_number_reflns         5134
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.863
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0383
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1167
_reflns_Friedel_coverage         0.617
_reflns_Friedel_fraction_full    0.981
_reflns_Friedel_fraction_max     0.756
_reflns_number_gt                4719
_reflns_number_total             5134
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc09106j2a.cif
_cod_data_source_block           mo_AFG74_0m
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7116448
_shelx_estimated_absorpt_t_min   0.888
_shelx_estimated_absorpt_t_max   0.942
_shelxl_version_number           2014/6
_shelx_res_checksum              75809
_shelx_hkl_checksum              97273