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_4133740
_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            'C54.5 H39 Al Cl F12 N O4'
_chemical_formula_weight         1062.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2054(5)
_cell_length_b                   22.5851(16)
_cell_length_c                   26.1244(15)
_cell_measurement_reflns_used    3864
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.5200
_cell_measurement_theta_min      3.4360
_cell_volume                     4841.4(5)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 10.3782
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0955
_diffrn_reflns_av_unetI/netI     0.1099
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            32779
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.849
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.248
_diffrn_reflns_theta_min         3.411
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.15223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       needles
_exptl_crystal_F_000             2172
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         1.282
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.092
_refine_ls_abs_structure_details
; 
 Flack x determined using 1758 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.02(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     777
_refine_ls_number_reflns         10153
_refine_ls_number_restraints     323
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1562
_refine_ls_R_factor_gt           0.0985
_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^)+(0.1766P)^2^+0.5404P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2511
_refine_ls_wR_factor_ref         0.2991
_reflns_Friedel_coverage         0.676
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.771
_reflns_number_gt                6029
_reflns_number_total             10153
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b10364_si_004.cif
_cod_data_source_block           exp_130
_cod_original_formula_sum        'C54.50 H39 Al Cl F12 N O4'
_cod_database_code               4133740
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.936
_shelx_estimated_absorpt_t_max   0.981
_shelx_res_checksum              2934
_shelx_hkl_checksum              57068