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_4128306
_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         'C23 H21 N O3 S'
_chemical_formula_sum            'C23 H21 N O3 S'
_chemical_formula_weight         391.47
_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-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 97.001(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.5476(3)
_cell_length_b                   8.4528(5)
_cell_length_c                   21.0022(13)
_cell_measurement_reflns_used    404
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.328
_cell_measurement_theta_min      2.119
_cell_volume                     977.51(10)
_computing_cell_refinement
'SHELXTL, Acta Cryst., Sect. A 2008, 64, 112-122.'
_computing_data_collection       'APEX3 v2018.1.0'
_computing_data_reduction        'Saint, APEX v2018.1.0.'
_computing_molecular_graphics    Ortep3
_computing_publication_material  'APEX3 v2018.1.0'
_computing_structure_refinement  'SHELXTL-2016/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT, Acta Cryst., Sect. A 2015, A71, 3-8.'
_diffrn_ambient_temperature      293(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  0.0940
_diffrn_reflns_av_unetI/netI     0.0644
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            16356
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.328
_diffrn_reflns_theta_min         2.119
_exptl_absorpt_coefficient_mu    1.665
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.592
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_description       platelet
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.352
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.078
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 953 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.071(17)
_refine_ls_extinction_coef       0.0073(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     255
_refine_ls_number_reflns         3552
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0428
_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^)+(0.0214P)^2^+0.1424P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0902
_reflns_Friedel_coverage         0.842
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.975
_reflns_number_gt                2647
_reflns_number_total             3552
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b07251_si_001.cif
_cod_data_source_block           Z_YL_II_15A_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4128306
_shelx_estimated_absorpt_t_min   0.592
_shelx_estimated_absorpt_t_max   0.881
_shelx_res_checksum              64957
_shelx_hkl_checksum              76145