Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual Catalysis.
Tasker, Sarah Z.; Jamison, Timothy F.; Journal of the American Chemical Society 137 (2015) 9531–9534; doi:10.1021/jacs.5b05597

data_4124179
_publ_section_title
;
 Highly Regioselective Indoline Synthesis under Nickel/Photoredox Dual
 Catalysis.
;
_journal_issue                   30
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9531
_journal_page_last               9534
_journal_paper_doi               10.1021/jacs.5b05597
_journal_volume                  137
_journal_year                    2015
_chemical_formula_sum            'C41 H56 I N3 Ni O3'
_chemical_formula_weight         824.49
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                68.5985(9)
_cell_angle_beta                 77.8452(10)
_cell_angle_gamma                82.4777(10)
_cell_formula_units_Z            2
_cell_length_a                   11.9159(2)
_cell_length_b                   13.6522(3)
_cell_length_c                   13.8179(3)
_cell_measurement_reflns_used    9083
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.68
_cell_measurement_theta_min      2.16
_cell_volume                     2042.34(7)
_computing_cell_refinement       'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_data_collection       'APEX2 v2011.4.0 (Bruker-AXS, 2011)'
_computing_data_reduction        'SAINT 7.46A (Bruker-AXS, 2011)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Smart APEX CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_unetI/netI     0.0196
_diffrn_reflns_laue_measured_fraction_full 1.000
_diffrn_reflns_laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            99315
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.574
_diffrn_reflns_theta_min         1.605
_diffrn_source                   'fine-focus sealed tube, graphite'
_exptl_absorpt_coefficient_mu    1.269
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.080
_refine_diff_density_max         1.083
_refine_diff_density_min         -0.772
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         11448
_refine_ls_number_restraints     2133
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.0311
_refine_ls_R_factor_gt           0.0251
_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^)+(0.0310P)^2^+1.0384P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0593
_refine_ls_wR_factor_ref         0.0631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10142
_reflns_number_total             11448
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b05597_si_003.cif
_cod_data_source_block           14042
_cod_depositor_comments
'Adding full bibliography for 4124179--4124180.cif.'
_cod_database_code               4124179
_shelx_estimated_absorpt_t_min   0.718
_shelx_estimated_absorpt_t_max   0.905
_shelxl_version_number           2014/6
_shelx_res_checksum              13725
_shelx_hkl_checksum              99577