Py-2NO ligand enabled Ni(ii)-catalyzed asymmetric Michael addition reaction of indoles with β,γ-unsaturated α-keto esters
Chen, Zi-Yue; Wang, Xi-Rui; Xu, Ke-Lan; Hu, Pan; Tian, You-Ping; Wang, Hui-Juan; Zhou, Ying; Liu, Xiong-Li; New Journal of Chemistry 48 (2024) 1688–1695; doi:10.1039/D3NJ05076A

data_7062947
_publ_section_title
;
 Py-2NO ligand enabled Ni(ii)-catalyzed asymmetric Michael addition
 reaction of indoles with \b,\g-unsaturated \a-keto esters
;
_journal_issue                   4
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              1688
_journal_page_last               1695
_journal_paper_doi               10.1039/D3NJ05076A
_journal_volume                  48
_journal_year                    2024
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C29 H29 N5 O2, 0.5(H4 O2)'
_chemical_formula_sum            'C29 H31 N5 O3'
_chemical_formula_weight         497.59
_space_group_crystal_system      trigonal
_space_group_IT_number           154
_space_group_name_Hall           'P 32 2"'
_space_group_name_H-M_alt        'P 32 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-05-13
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-09-01 deposited with the CCDC.	2023-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   9.35380(10)
_cell_length_b                   9.35380(10)
_cell_length_c                   24.4673(3)
_cell_measurement_reflns_used    8147
_cell_measurement_temperature    162(18)
_cell_measurement_theta_max      71.2780
_cell_measurement_theta_min      5.4160
_cell_volume                     1853.93(4)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      162(18)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     78.00 103.00   0.50    0.50    --   42.30  38.00 150.00   50
  2  \w     11.00 131.00   0.50    0.50    --   42.30  38.00   0.00  240
  3  \w     81.00 131.00   0.50    0.50    --   42.30  77.00  30.00  100
  4  \w     80.00 132.00   0.50    0.50    --   42.30  77.00-150.00  104
  5  \w     -5.00  37.00   0.50    0.50    --   42.30  38.00 150.00   84
  6  \w     88.00 114.00   0.50    0.50    --   42.30  77.00 150.00   52
  7  \w     98.00 131.00   0.50    0.50    --   42.30  77.00 -60.00   66
  8  \w     94.00 120.00   0.50    0.50    --   42.30  77.00-180.00   52
  9  \w     70.00 178.00   0.50    0.50    --  101.60  50.00 150.00  216
 10  \w     74.00 190.00   0.50    0.50    --  101.60  50.00  60.00  232
 11  \w     70.00 191.00   0.50    0.50    --  101.60  50.00  90.00  242
 12  \w     20.00 124.00   0.50    0.50    --  101.60 -64.00-120.00  208
 13  \w     87.00 113.00   0.50    0.50    --  101.60  77.00  30.00   52
 14  \w    143.00 190.00   0.50    0.50    --  101.60  82.00 150.00   94
 15  \w    131.00 157.00   0.50    0.50    --  101.60  77.00  60.00   52
 16  \w    134.00 150.00   0.50    0.50    --  101.60  50.00 120.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1486719000
_diffrn_orient_matrix_UB_12      0.1479078000
_diffrn_orient_matrix_UB_13      -0.0273974000
_diffrn_orient_matrix_UB_21      0.0238943000
_diffrn_orient_matrix_UB_22      -0.1191863000
_diffrn_orient_matrix_UB_23      -0.0372897000
_diffrn_orient_matrix_UB_31      -0.1160653000
_diffrn_orient_matrix_UB_32      0.0091521000
_diffrn_orient_matrix_UB_33      -0.0427343000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0136
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            8924
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.405
_diffrn_reflns_theta_min         5.424
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.713
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.03771
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.064
_refine_ls_abs_structure_details
;
 Flack x determined using 952 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2390
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.085
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0378
_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^)+(0.0639P)^2^+0.4867P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1037
_reflns_Friedel_coverage         0.680
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2379
_reflns_number_total             2390
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj05076a2.cif
_cod_data_source_block           c-1
_cod_depositor_comments
'Adding full bibliography for 7062946--7062948.cif.'
_cod_original_cell_volume        1853.93(5)
_cod_database_code               7062947
_shelx_shelxl_version_number     2018/3
_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 O(H,H) groups
2. Others
 Fixed Sof: H2A(0.5) H2B(0.5)
3.a Free rotating group:
 O2(H2A,H2B)
3.b Ternary CH refined with riding coordinates:
 C8(H8), C13(H13)
3.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C15(H15), C16(H16)
;
_shelx_res_checksum              6080
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 18.774
_oxdiff_exptl_absorpt_empirical_full_min 0.755