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_4124180
_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            'C43 H59 N3 Ni O'
_chemical_formula_weight         692.64
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                91.6260(19)
_cell_angle_beta                 109.3194(17)
_cell_angle_gamma                114.9560(18)
_cell_formula_units_Z            2
_cell_length_a                   11.6854(8)
_cell_length_b                   13.0659(9)
_cell_length_c                   14.9978(10)
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      31.49
_cell_measurement_theta_min      2.96
_cell_volume                     1921.0(2)
_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 APEX2 CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0217
_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       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            79302
_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         30.999
_diffrn_reflns_theta_min         1.467
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.541
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2009)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.197
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             748
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.740
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     451
_refine_ls_number_reflns         12233
_refine_ls_number_restraints     85
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0327
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0416P)^2^+0.9938P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0881
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11320
_reflns_number_total             12233
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b05597_si_002.cif
_cod_data_source_block           X15054
_cod_depositor_comments
'Adding full bibliography for 4124179--4124180.cif.'
_cod_database_code               4124180
_shelx_estimated_absorpt_t_min   0.817
_shelx_estimated_absorpt_t_max   0.859
_shelxl_version_number           2014/6
_shelx_res_checksum              40821
_shelx_hkl_checksum              16413