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_4514666
_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_sum            'C108 H92 Cl12 N8 O4'
_chemical_formula_weight         1991.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 91.7380(10)
_cell_angle_gamma                90
_cell_formula_units_Z            1
_cell_length_a                   16.9269(5)
_cell_length_b                   16.7619(5)
_cell_length_c                   8.8583(3)
_cell_measurement_reflns_used    9899
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.5398
_cell_measurement_theta_min      2.2709
_cell_volume                     2512.18(14)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            10041
_diffrn_reflns_point_group_measured_fraction_full 0.696
_diffrn_reflns_point_group_measured_fraction_max 0.696
_diffrn_reflns_theta_full        65.043
_diffrn_reflns_theta_max         65.043
_diffrn_reflns_theta_min         3.712
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    3.473
_exptl_absorpt_correction_T_max  0.788
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET)
(compiled Nov  6 2009,16:24:50)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       acicular
_exptl_crystal_F_000             1032
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 834 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.062(9)
_refine_ls_extinction_coef       0.00196(17)
_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   1.071
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     391
_refine_ls_number_reflns         2977
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.0317
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0395P)^2^+1.5790P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0811
_refine_ls_wR_factor_ref         0.0813
_reflns_Friedel_coverage         0.405
_reflns_Friedel_fraction_full    0.402
_reflns_Friedel_fraction_max     0.402
_reflns_number_gt                2960
_reflns_number_total             2977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs9b02081_si_003.cif
_cod_data_source_block           cu_pyy_3_9_0m
_cod_database_code               4514666
_shelx_shelxl_version_number     2014/7
_exptl_absorpt_special_details
;
 ?
;
_shelx_res_checksum              92020
_shelx_hkl_checksum              37721