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_1553777
_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         ' C10 H12 O2 S'
_chemical_formula_sum            'C10 H12 O2 S'
_chemical_formula_weight         196.26
_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
_audit_update_record
;
2017-03-15 deposited with the CCDC.
2017-05-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.7817(12)
_cell_length_b                   8.2558(10)
_cell_length_c                   19.972(2)
_cell_measurement_reflns_used    7254
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      5.80
_cell_volume                     953.3(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0918
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            7722
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.297
_diffrn_reflns_theta_min         5.799
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    2.721
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.312
_refine_diff_density_rms         0.050
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     119
_refine_ls_number_reflns         1709
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0340
_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^)+(0.0438P)^2^+0.3361P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0898
_refine_ls_wR_factor_ref         0.0900
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                1701
_reflns_number_total             1709
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00248c2.cif
_cod_data_source_block           a
_cod_original_formula_sum        ' C10 H12 O2 S'
_cod_database_code               1553777
_shelxl_version_number           2014-3
_shelx_res_checksum              84706
_shelx_hkl_checksum              78700