Ruthenium-Catalyzed Enantioselective C-H Functionalization: A Practical Access to Optically Active Indoline Derivatives.
Li, Zhong-Yuan; Lakmal, Hetti Handi Chaminda; Qian, Xiaolin; Zhu, Zhenyu; Donnadieu, Bruno; McClain, Sarah J.; Xu, Xue; Cui, Xin; Journal of the American Chemical Society 141 (2019) 15730–15736; doi:10.1021/jacs.9b07251

data_4128305
_publ_section_title
;
 Ruthenium-Catalyzed Enantioselective C-H Functionalization: A Practical
 Access to Optically Active Indoline Derivatives.
;
_journal_issue                   40
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              15730
_journal_page_last               15736
_journal_paper_doi               10.1021/jacs.9b07251
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C30 H31 Cl4 N Ru'
_chemical_formula_sum            'C30 H31 Cl4 N Ru'
_chemical_formula_weight         648.43
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8236(2)
_cell_length_b                   14.7618(4)
_cell_length_c                   24.4735(7)
_cell_measurement_reflns_used    1475
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      66.857
_cell_measurement_theta_min      3.496
_cell_volume                     2826.45(13)
_computing_cell_refinement       'APEX3 v2018.7.2'
_computing_data_collection       'APEX3 v2018.7.2'
_computing_data_reduction        'Saint, APEX v2018.7.2.'
_computing_molecular_graphics    'POV-Ray v 3.7'
_computing_publication_material  'APEX3 v2018.7.2'
_computing_structure_refinement  'SHELXTL-2016/6 (Sheldrick, 2014)'
_computing_structure_solution    SHELXL2018/3
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker AXS D8 Venture '
_diffrn_measurement_method       'profile data from \q/2\q scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_av_unetI/netI     0.0487
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            50230
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        66.857
_diffrn_reflns_theta_max         66.857
_diffrn_reflns_theta_min         3.496
_exptl_absorpt_coefficient_mu    8.116
_exptl_absorpt_correction_T_max  0.770
_exptl_absorpt_correction_T_min  0.166
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_description       platelet
_exptl_crystal_F_000             1320
_exptl_crystal_size_max          0.345
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.034
_refine_diff_density_max         0.692
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.074
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.016(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         5016
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0309
_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^)+(0.0241P)^2^+1.3668P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0607
_refine_ls_wR_factor_ref         0.0625
_reflns_Friedel_coverage         0.747
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                4603
_reflns_number_total             5016
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07251_si_002.cif
_cod_data_source_block           Cu_Xui062419_final
_cod_database_code               4128305
_shelx_estimated_absorpt_t_min   0.166
_shelx_estimated_absorpt_t_max   0.770
_shelx_res_checksum              80677
_shelx_hkl_checksum              68877