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_7062946
_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 O6, 6(H2 O)'
_chemical_formula_sum            'C29 H41 N5 O12'
_chemical_formula_weight         651.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'I 2y'
_space_group_name_H-M_alt        'I 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-29
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-06-04 deposited with the CCDC.	2023-12-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.351(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.5408(7)
_cell_length_b                   8.9758(5)
_cell_length_c                   16.0958(7)
_cell_measurement_reflns_used    2908
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.1740
_cell_measurement_theta_min      4.6780
_cell_volume                     1506.71(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.970
_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   -115.00 -16.00   1.00    1.00    --  -40.23 -37.00  60.00   99
  2  \w    -73.00  36.00   1.00    1.00    --  -40.23  77.00 -60.00  109
  3  \w   -115.00 -16.00   1.00    1.00    --  -40.23 -37.00   0.00   99
  4  \w    -96.00  -2.00   1.00    1.00    --  -40.23 125.00 150.00   94
  5  \w     22.00  47.00   1.00    1.00    --   40.23  37.00-180.00   25
  6  \w      1.00  78.00   1.00    1.00    --   40.23 -99.00 150.00   77
  7  \w     76.00 166.00   1.00    1.20    --  108.83  77.00  30.00   90
  8  \w     38.00  78.00   1.00    1.20    --  108.83-125.00 -90.00   40
  9  \w     82.00 110.00   1.00    1.20    --  108.83  61.00  30.00   28
 10  \w     85.00 112.00   1.00    1.20    --  108.83  61.00   0.00   27
 11  \w    104.00 169.00   1.00    1.20    --  108.83 111.00-166.00   65
 12  \w     31.00 161.00   1.00    1.20    --  108.83 -15.00  30.00  130
 13  \w    135.00 164.00   1.00    1.20    --  108.83  77.00  90.00   29
 14  \w     81.00 127.00   1.00    1.20    --  108.83  61.00  60.00   46
 15  \w     76.00 176.00   1.00    1.20    --  108.83  77.00  60.00  100
 16  \w    125.00 152.00   1.00    1.20    --  108.83  77.00   0.00   27
 17  \w     82.00 108.00   1.00    1.20    --  108.83  61.00  90.00   26
 18  \w     80.00 151.00   1.00    1.20    --  108.83  61.00 120.00   71
 19  \w     50.00  79.00   1.00    1.20    --  108.83 -94.00 -90.00   29
 20  \w     76.00 103.00   1.00    1.20    --  108.83  77.00   0.00   27
 21  \w     76.00 103.00   1.00    1.20    --  108.83  77.00  90.00   27
 22  \w     40.00  75.00   1.00    1.20    --  108.83 -61.00  60.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0662604000
_diffrn_orient_matrix_UB_12      -0.0210855000
_diffrn_orient_matrix_UB_13      -0.0784234000
_diffrn_orient_matrix_UB_21      0.1101260000
_diffrn_orient_matrix_UB_22      -0.0853613000
_diffrn_orient_matrix_UB_23      0.0530768000
_diffrn_orient_matrix_UB_31      -0.0731052000
_diffrn_orient_matrix_UB_32      -0.1473272000
_diffrn_orient_matrix_UB_33      -0.0194782000
_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  0.0253
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4899
_diffrn_reflns_point_group_measured_fraction_full 0.930
_diffrn_reflns_point_group_measured_fraction_max 0.890
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.805
_diffrn_reflns_theta_min         4.719
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.949
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.21815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       block
_exptl_crystal_F_000             692
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.440
_refine_diff_density_min         -0.773
_refine_diff_density_rms         0.097
_refine_ls_abs_structure_details
;
 Flack x determined using 938 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.06(18)
_refine_ls_extinction_coef       0.0035(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0710
_refine_ls_R_factor_gt           0.0647
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1160P)^2^+2.5360P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1763
_refine_ls_wR_factor_ref         0.1830
_reflns_Friedel_coverage         0.722
_reflns_Friedel_fraction_full    0.855
_reflns_Friedel_fraction_max     0.800
_reflns_number_gt                2515
_reflns_number_total             2755
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj05076a2.cif
_cod_data_source_block           d62-2no
_cod_depositor_comments
'Adding full bibliography for 7062946--7062948.cif.'
_cod_original_cell_volume        1506.70(14)
_cod_database_code               7062946
_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) groups, All O(H,H) groups
2. Others
 Fixed Sof: H2WA(0.5) H2WB(0.5) H3WA(0.5) H3WB(0.5)
3.a Free rotating group:
 O1W(H1WA,H1WB), O2W(H2WA,H2WB), O3W(H3WA,H3WB), O4W(H4WA,H4WB)
3.b Ternary CH refined with riding coordinates:
 C8(H8), C10(H10), C12(H12)
3.c Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C11(H11A,H11B)
3.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6), C14(H14), C15(H15)
3.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              7252
_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 3.569
_oxdiff_exptl_absorpt_empirical_full_min 0.559