Synthesis of chiral chromanols via a RuPHOX-Ru catalyzed asymmetric hydrogenation of chromones.
Ma, Yujie; Li, Jing; Ye, Jianxun; Liu, Delong; Zhang, Wanbin; Chemical communications (Cambridge, England) 54 (2018) 13571–13574; doi:10.1039/c8cc07787h

data_7122583
_publ_section_title
;
 Synthesis of chiral chromanols via a RuPHOX-Ru catalyzed asymmetric
 hydrogenation of chromones.
;
_journal_issue                   96
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              13571
_journal_page_last               13574
_journal_paper_doi               10.1039/c8cc07787h
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C10 H12 O2'
_chemical_formula_sum            'C10 H12 O2'
_chemical_formula_weight         164.20
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_audit_update_record
;
2018-09-28 deposited with the CCDC.
2018-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.13(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.506(10)
_cell_length_b                   4.840(8)
_cell_length_c                   16.85(2)
_cell_measurement_reflns_used    4416
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      68.07
_cell_measurement_theta_min      2.68
_cell_volume                     914(2)
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.953
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0616
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.953
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6738
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.955
_diffrn_reflns_theta_full        59.368
_diffrn_reflns_theta_max         59.368
_diffrn_reflns_theta_min         2.693
_exptl_absorpt_coefficient_mu    0.663
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       block
_exptl_crystal_F_000             352
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_transmission_factor_max   0.7531
_exptl_transmission_factor_min   0.5070
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         2470
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0696
_refine_ls_R_factor_gt           0.0556
_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^)+(0.0574P)^2^+0.2010P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1365
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.761
_reflns_Friedel_fraction_full    0.958
_reflns_Friedel_fraction_max     0.957
_reflns_number_gt                2021
_reflns_number_total             2470
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc07787h2.cif
_cod_data_source_block           t_a
_cod_depositor_comments
'Adding full bibliography for 7122581--7122584.cif.'
_cod_database_code               7122583
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.868
_shelx_estimated_absorpt_t_max   0.884
_shelx_res_checksum              99351
_shelx_hkl_checksum              92841