Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.
Lebedev, Yury N.; Polishchuk, Iuliia; Maity, Bholanath; Cavallo, Luigi; Rueping, Magnus; Journal of the American Chemical Society  (2019) –; doi:10.1021/jacs.9b10364

data_4133741
_publ_section_title
;
 Asymmetric Hydroboration of Heteroaryl Ketones by Aluminum Catalysis.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.9b10364
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C13 H20 B N O3'
_chemical_formula_weight         249.11
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.465(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.3514(10)
_cell_length_b                   13.1538(9)
_cell_length_c                   14.7984(10)
_cell_measurement_reflns_used    9048
_cell_measurement_temperature    125(2)
_cell_measurement_theta_max      33.15
_cell_measurement_theta_min      2.23
_cell_volume                     2727.7(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      125(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0712
_diffrn_reflns_av_unetI/netI     0.0657
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            96736
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.181
_diffrn_reflns_theta_min         1.793
_diffrn_source                   'sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.6399
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.213
_exptl_crystal_description       block
_exptl_crystal_F_000             1072
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 6367 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         20714
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0567
_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^)+(0.0675P)^2^+0.6647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1310
_refine_ls_wR_factor_ref         0.1444
_reflns_Friedel_coverage         0.924
_reflns_Friedel_fraction_full    0.991
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                16604
_reflns_number_total             20714
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10364_si_005.cif
_cod_data_source_block           AcPyHBPin
_cod_depositor_comments
;

2020-05-25
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_sg_symbol_H-M      'P 21'
_cod_original_formula_sum        'C52 H80 B4 N4 O12'
_cod_original_formula_units_Z    2
_cod_original_formula_weight     996.44
_cod_database_code               4133741
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.921
_shelx_estimated_absorpt_t_max   0.959
_shelx_res_checksum              31037
_shelx_hkl_checksum              24254