Iridium-Catalyzed Asymmetric Hydrogenation of 2H-Chromenes: A Highly Enantioselective Approach to Isoflavan Derivatives.
Xia, Jingzhao; Nie, Yu; Yang, Guoqiang; Liu, Yangang; Zhang, Wanbin; Organic letters 19 (2017) 4884–4887; doi:10.1021/acs.orglett.7b02341

data_1547568
_publ_section_title
;
 Iridium-Catalyzed Asymmetric Hydrogenation of 2H-Chromenes: A Highly
 Enantioselective Approach to Isoflavan Derivatives.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4884
_journal_page_last               4887
_journal_paper_doi               10.1021/acs.orglett.7b02341
_journal_volume                  19
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C15 H13 Cl O'
_chemical_formula_sum            'C15 H13 Cl O'
_chemical_formula_weight         244.70
_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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.0030(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.76240(10)
_cell_length_b                   22.9736(6)
_cell_length_c                   9.5587(2)
_cell_measurement_reflns_used    9983
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      4.81
_cell_volume                     1216.37(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker D8 VENTURE CMOS photon 100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12176
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.292
_diffrn_reflns_theta_min         4.813
_exptl_absorpt_coefficient_mu    2.598
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details
;
 Flack x determined using 1934 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.048(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.661
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4315
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.661
_refine_ls_R_factor_all          0.0251
_refine_ls_R_factor_gt           0.0244
_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          0.0738
_refine_ls_wR_factor_ref         0.0749
_reflns_Friedel_coverage         0.902
_reflns_Friedel_fraction_full    0.946
_reflns_Friedel_fraction_max     0.945
_reflns_number_gt                4220
_reflns_number_total             4315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b02341_si_002.cif
_cod_data_source_block           t_a
_cod_database_code               1547568
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.625
_shelx_estimated_absorpt_t_max   0.625
_shelx_res_checksum              36651
_shelx_hkl_checksum              31787