Ni-Catalyzed Regio- and Enantioselective Domino Reductive Cyclization: One-Pot Synthesis of 2,3-Fused Cyclopentannulated Indolines
Ping, Yuanyuan; Wang, Kuai; Pan, Qi; Ding, Zhengtian; Zhou, Zhijun; Guo, Ya; Kong, Wangqing; ACS Catalysis 9 (2019) 7335–; doi:10.1021/acscatal.9b02081

data_4514665
_publ_section_title
;
 Ni-Catalyzed Regio- and Enantioselective Domino Reductive Cyclization:
 One-Pot Synthesis of 2,3-Fused Cyclopentannulated Indolines
;
_journal_issue                   8
_journal_name_full               'ACS Catalysis'
_journal_page_first              7335
_journal_paper_doi               10.1021/acscatal.9b02081
_journal_volume                  9
_journal_year                    2019
_chemical_formula_moiety         'C20 H21 N'
_chemical_formula_sum            'C20 H21 N'
_chemical_formula_weight         275.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-04-25
_audit_creation_method
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_cell_angle_alpha                90
_cell_angle_beta                 90.785(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.2763(6)
_cell_length_b                   11.8965(6)
_cell_length_c                   12.9403(7)
_cell_measurement_reflns_used    9928
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      69.45
_cell_measurement_theta_min      3.42
_cell_volume                     1581.83(15)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            16635
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.255
_diffrn_reflns_theta_min         4.303
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.502
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6113
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.156
_exptl_crystal_description       block
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.187
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0063(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     194
_refine_ls_number_reflns         2814
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.124
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0561
_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^)+(0.0427P)^2^+0.7781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1411
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2561
_reflns_number_total             2814
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02081_si_002.cif
_cod_data_source_block           cu_190423b_0m
_cod_database_code               4514665
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups 
 At 1.5 times of: 
  All C(H,H,H) groups 
2.a Ternary CH refined with riding coordinates: 
 C5(H5) 
2.b Secondary CH2 refined with riding coordinates: 
 C3(H3A,H3B) 
2.c Aromatic/amide H refined with riding coordinates: 
 C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17), C18(H18), 
 C19(H19) 
2.d Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C13(H13A,H13B,H13C), C20(H20A,H20B,H20C) 
;
_shelx_res_checksum              83184
_shelx_hkl_checksum              7487
_olex2_submission_special_instructions 'No special instructions were received'