Asymmetric addition of Grignard reagents to ketones: culmination of the ligand-mediated methodology allows modular construction of chiral tertiary alcohols
Monasterolo, Claudio; O'Gara, Ryan; Kavanagh, Saranna; Byrne, Sadbh Elise; Bieszczad, Bartosz; Murray, Orla; Wiesinger, Michael; Lynch, Rebecca; Nikitin, Kirill; Gilheany, Declan Gerard; Chemical Science  (2022) –; doi:10.1039/D1SC06350B

data_1566845
_publ_section_title
;
 Asymmetric addition of Grignard reagents to ketones: culmination of the
 ligand-mediated methodology allows modular construction of chiral
 tertiary alcohols
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC06350B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         '2 (C48 H83 Br3 Mg3 N4 O3), 3 (C7 H8)'
_chemical_formula_sum            'C117 H190 Br6 Mg6 N8 O6'
_chemical_formula_weight         2430.09
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2022-03-14 deposited with the CCDC.	2022-03-30 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 93.454(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   19.2717(2)
_cell_length_b                   16.1154(2)
_cell_length_c                   19.6920(3)
_cell_measurement_reflns_used    21334
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      75.1470
_cell_measurement_theta_min      3.5210
_cell_volume                     6104.66(14)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3196
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0620
_diffrn_reflns_av_sigmaI/netI    0.0730
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            79195
_diffrn_reflns_theta_full        76.92
_diffrn_reflns_theta_max         76.92
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    3.090
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_correction_T_min  0.783
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
; 
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015) 
Numerical absorption correction based on gaussian integration over 
a multifaceted crystal model 
Empirical absorption correction using spherical harmonics, 
implemented in SCALE3 ABSPACK scaling algorithm. 
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2556
_exptl_crystal_size_max          0.126
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.017
_refine_diff_density_max         1.256
_refine_diff_density_min         -0.817
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.019(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1328
_refine_ls_number_reflns         24793
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0576
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0534P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0991
_refine_ls_wR_factor_ref         0.1078
_reflns_number_gt                20800
_reflns_number_total             24793
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            d1sc06350b2.cif
_cod_data_source_block           gil92
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1566845