Nickel-catalyzed C3-alkylation of indoles with alcohols via a borrowing hydrogen strategy
Hu, Miao; Jiang, Yong; Sun, Nan; Hu, Baoxiang; Shen, Zhenlu; Hu, Xinquan; Jin, Liqun; New Journal of Chemistry 45 (2021) 10057–10062; doi:10.1039/D1NJ01581H

data_7060660
_publ_section_title
;
 Nickel-catalyzed C3-alkylation of indoles with alcohols via a borrowing
 hydrogen strategy
;
_journal_issue                   22
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10057
_journal_page_last               10062
_journal_paper_doi               10.1039/D1NJ01581H
_journal_volume                  45
_journal_year                    2021
_chemical_formula_moiety         'C32 H34 Cl4 N2 Ni2 O4'
_chemical_formula_sum            'C32 H34 Cl4 N2 Ni2 O4'
_chemical_formula_weight         769.83
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-13
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145)
;
_audit_update_record
;
2021-01-07 deposited with the CCDC.	2021-05-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0105(6)
_cell_length_b                   11.6307(5)
_cell_length_c                   21.7397(9)
_cell_measurement_reflns_used    6375
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.349
_cell_measurement_theta_min      2.529
_cell_volume                     3289.7(2)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0589
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            26736
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.502
_diffrn_reflns_theta_min         2.442
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.509
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1155 before and 0.0535 after correction.
The Ratio of minimum to maximum transmission is 0.8836.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.554
_exptl_crystal_description       block
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.062
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3772
_refine_ls_number_restraints     10
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0318
_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^)+(0.0266P)^2^+2.7145P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0676
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2900
_reflns_number_total             3772
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1nj01581h2.cif
_cod_data_source_block           a
_cod_depositor_comments          'Adding full bibliography for 7060660.cif.'
_cod_database_code               7060660
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.864
_shelx_estimated_absorpt_t_min   0.840
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Restrained distances
 O3-H3
 0.85 with sigma of 0.01
 H3-O3
 0.82 with sigma of 0.02
 Ni1-H3
 2.763848 with sigma of 0.02
 C1-H3
 2.5 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C10A \\sim C10: within 2A with sigma of 0.005 and sigma for terminal atoms of
0.01 within 2A
4. Others
 Sof(H9BC)=Sof(H9BD)=Sof(H11C)=Sof(H11D)=Sof(C10A)=Sof(H10C)=Sof(H10D)=1-FVAR(1)
 Sof(H9AA)=Sof(H9AB)=Sof(H11A)=Sof(H11B)=Sof(C10)=Sof(H10A)=Sof(H10B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C9(H9AA,H9AB), C9(H9BC,H9BD), C1(H1A,H1B), C11(H11A,H11B), C11(H11C,H11D),
 C10(H10A,H10B), C10A(H10C,H10D)
5.b Aromatic/amide H refined with riding coordinates:
 C16(H16), C15(H15), C14(H14), C3(H3A), C7(H7), C4(H4), C5(H5), C6(H6)
;
_shelx_res_checksum              74554
_olex2_submission_special_instructions 'No special instructions were received'