Ir/BiphPHOX-catalyzed asymmetric hydrogenation of 3-substituted 2,5-dihydropyrroles and 2,5-dihydrothiophene 1,1-dioxides
Meng, Ke; Xia, Jingzhao; Wang, Yanzhao; Zhang, Xinghua; Yang, Guoqiang; Zhang, Wanbin; Organic Chemistry Frontiers 4 (2017) 1601–; doi:10.1039/C7QO00248C

data_1553778
_publ_section_title
;
 Ir/BiphPHOX-catalyzed asymmetric hydrogenation of 3-substituted
 2,5-dihydropyrroles and 2,5-dihydrothiophene 1,1-dioxides
;
_journal_issue                   8
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1601
_journal_paper_doi               10.1039/C7QO00248C
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C17 H19 N O2 S'
_chemical_formula_sum            'C17 H19 N O2 S'
_chemical_formula_weight         301.39
_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
_audit_update_record
;
2017-03-15 deposited with the CCDC.
2017-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.45
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.3637(4)
_cell_length_b                   6.0455(3)
_cell_length_c                   11.3636(4)
_cell_measurement_reflns_used    4049
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.39
_cell_measurement_theta_min      3.93
_cell_volume                     772.20(5)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_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  0.0501
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7602
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.542
_diffrn_reflns_theta_min         3.933
_exptl_absorpt_coefficient_mu    1.889
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.296
_exptl_crystal_description       block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2362
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0352
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0353P)^2^+0.1143P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0792
_refine_ls_wR_factor_ref         0.0830
_reflns_Friedel_coverage         0.816
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                2130
_reflns_number_total             2362
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00248c2.cif
_cod_data_source_block           t
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1553778
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.681
_shelx_estimated_absorpt_t_max   0.765
_shelx_res_checksum              48448
_shelx_hkl_checksum              7134