Enantioselective Assembly of Cycloenones with a Nitrile-Containing All-Carbon Quaternary Center from Malononitriles Enabled by Ni Catalysis.
Lu, Zhiwu; Hu, Xu-Dong; Zhang, Hui; Zhang, Xiao-Wen; Cai, Jinhui; Usman, Muhammad; Cong, Hengjiang; Liu, Wen-Bo; Journal of the American Chemical Society 142 (2020) 7328–7333; doi:10.1021/jacs.0c02075

data_4134698
_publ_section_title
;
 Enantioselective Assembly of Cycloenones with a Nitrile-Containing
 All-Carbon Quaternary Center from Malononitriles Enabled by Ni Catalysis.
;
_journal_issue                   16
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7328
_journal_page_last               7333
_journal_paper_doi               10.1021/jacs.0c02075
_journal_volume                  142
_journal_year                    2020
_chemical_formula_moiety         'C26 H23 N O'
_chemical_formula_sum            'C26 H23 N O'
_chemical_formula_weight         365.45
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_audit_creation_date             2019-09-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 96.4970(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.43000(10)
_cell_length_b                   12.18180(10)
_cell_length_c                   25.8958(2)
_cell_measurement_reflns_used    14167
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      73.9000
_cell_measurement_theta_min      3.3840
_cell_volume                     2015.36(4)
_computing_cell_refinement
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_collection
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_computing_data_reduction
'CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)'
_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    'XT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      200.00(10)
_diffrn_detector                 'Hybrid Pixel Counting (HPC) detector'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku HyPix-6000HE'
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.980
_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    -22.00   4.00   0.50    0.50    --    5.00 -57.00 150.00   52
  2  \w    -54.00 -28.00   0.50    0.50    --    5.00 -57.00 150.00   52
  3  \w    -25.00  94.00   0.50    0.50    --    5.00  57.00-180.00  238
  4  \w     61.00  93.00   0.50    0.50    --    5.00  57.00  30.00   64
  5  \w    -84.00 -13.00   0.50    0.50    --  -46.90  76.00 -90.00  142
  6  \w    -10.00  33.00   0.50    0.50    --  -46.90  76.00 -90.00   86
  7  \w   -133.00 -56.00   0.50    0.50    --  -46.90 -38.00-120.00  154
  8  \w   -141.00 -85.00   0.50    0.50    -- -102.20 -19.00 120.00  112
  9  \w   -186.00 -65.00   0.50    0.50    -- -102.20 -74.00 -18.62  242
 10  \w    -91.00 -66.00   0.50    0.50    -- -102.20 -70.00  39.29   50
 11  \w   -116.00 -13.00   0.50    0.50    -- -102.20  57.00  90.00  206
 12  \w   -104.00 -13.00   0.50    0.50    -- -102.20  76.00-180.00  182
 13  \w   -186.00 -66.00   0.50    0.50    -- -102.20 -38.00-180.00  240
 14  \w    -91.00 -65.00   0.50    0.50    -- -102.20 -76.00   0.00   52
 15  \w   -130.00-104.00   0.50    0.50    -- -102.20  57.00  60.00   52
 16  \w    -90.00 -65.00   0.50    0.50    -- -102.20 -72.00   3.53   50
 17  \w   -122.00 -97.00   0.50    0.50    -- -102.20  76.00   0.00   50
 18  \w    -94.00 -13.00   0.50    0.50    -- -102.20  76.00 -60.00  162
 19  \w   -139.00 -13.00   0.50    0.50    -- -102.20  76.00  90.00  252
 20  \w    -91.00 -66.00   0.50    0.50    -- -102.20 -71.00  15.64   50
 21  \w    -75.00 -49.00   0.50    0.50    -- -102.20 -19.00 120.00   52
 22  \w   -192.00-166.00   0.50    0.50    -- -102.20 -72.00   3.53   52
 23  \w   -165.00 -66.00   0.50    0.50    -- -102.20 -70.00  34.28  198
 24  \w   -120.00 -70.00   0.50    0.50    -- -102.20 -71.00  11.35  100
 25  \w   -162.00 -65.00   0.50    0.50    -- -102.20 -73.00  -1.27  194
 26  \w   -114.00 -89.00   0.50    0.50    -- -102.20  76.00  30.00   50
 27  \w    -90.00 -65.00   0.50    0.50    -- -102.20 -76.00  37.80   50
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'profile data from \w-scans and \phi-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0154513000
_diffrn_orient_matrix_UB_12      0.1138296000
_diffrn_orient_matrix_UB_13      0.0251875000
_diffrn_orient_matrix_UB_21      -0.0582544000
_diffrn_orient_matrix_UB_22      0.0511441000
_diffrn_orient_matrix_UB_23      -0.0541134000
_diffrn_orient_matrix_UB_31      -0.2335298000
_diffrn_orient_matrix_UB_32      -0.0202696000
_diffrn_orient_matrix_UB_33      0.0048267000
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  'VariMax VHF'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0237
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            21974
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.082
_diffrn_reflns_theta_min         3.436
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Cu
_diffrn_source_type              'Rigaku MicroMax-007HF'
_diffrn_source_voltage           40.0
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67484
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       needle
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.027
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     345
_refine_ls_number_reflns         4006
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0394
_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^)+(0.0487P)^2^+0.4410P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1009
_refine_ls_wR_factor_ref         0.1020
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3810
_reflns_number_total             4006
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c02075_si_002.cif
_cod_data_source_block           liuwenbo-lzw-2-15-2-200k-190917
_cod_depositor_comments
'Adding full bibliography for 4134698--4134699.cif.'
_cod_database_code               4134698
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'H C N O'
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 98.03
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     39.93
_olex2_refinement_description
;
;
_shelx_res_checksum              28325
_shelx_hkl_checksum              74739
_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 1.439
_oxdiff_exptl_absorpt_empirical_full_min 0.612