Ni-catalyzed Enantioselective Reductive Arylcyanation/Cyclization of N-(2-iodo-aryl) Acrylamide
Dong, Kaiwu; Wang, Guangzhu; Ren, Xinyi; Shen, Chaoren; Chemical Communications  (2022) –; doi:10.1039/D1CC04996H

data_7129393
_publ_section_title
;
 Ni-catalyzed Enantioselective Reductive Arylcyanation/Cyclization of
 N-(2-iodo-aryl) Acrylamide
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC04996H
_journal_year                    2022
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C16 H18 N2 O'
_chemical_formula_sum            'C16 H18 N2 O'
_chemical_formula_weight         254.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-03-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-05-12 deposited with the CCDC.	2021-12-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6715(2)
_cell_length_b                   9.0287(3)
_cell_length_c                   17.7211(5)
_cell_measurement_reflns_used    23172
_cell_measurement_temperature    169(2)
_cell_measurement_theta_max      74.1940
_cell_measurement_theta_min      4.8970
_cell_volume                     1387.43(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.32a (Rigaku OD, 2017)'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      169(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.985
_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    -19.00  24.00   1.00    1.00    --    0.00  38.00  30.00   43
  2  \w    -13.00  53.00   1.00    1.00    --    0.00  38.00-180.00   66
  3  \w     51.00  89.00   1.00    1.00    --    0.00  38.00 120.00   38
  4  \w    -45.00 -15.00   1.00    1.00    --    0.00 -57.00-120.00   30
  5  \w     -9.00  23.00   1.00    1.00    --    0.00 -57.00-120.00   32
  6  \w    -18.00  35.00   1.00    1.00    --    0.00  38.00 120.00   53
  7  \w     28.00  89.00   1.00    1.00    --    0.00  38.00  30.00   61
  8  \w    -79.00   2.00   1.00    1.00    --    0.00 -19.00 150.00   81
  9  \w    -18.00  85.00   1.00    1.00    --    0.00  38.00 -60.00  103
 10  \w    -28.00   9.00   1.00    1.00    --    0.00  77.00 120.00   37
 11  \w     71.00 126.00   1.00    1.00    --   95.80 -77.00  90.00   55
 12  \w     65.00  90.00   1.00    1.00    --   95.80  77.00-150.00   25
 13  \w     71.00  98.00   1.00    1.00    --   95.80  61.00 -90.00   27
 14  \w     65.00  90.00   1.00    1.00    --   95.80  77.00   0.00   25
 15  \w     65.00  91.00   1.00    1.00    --   95.80  77.00 120.00   26
 16  \w     31.00  67.00   1.00    1.00    --   95.80 -77.00  90.00   36
 17  \w     73.00 169.00   1.00    1.00    --   95.80  52.00  -6.28   96
 18  \w    104.00 169.00   1.00    1.00    --   95.80  82.00 -60.00   65
 19  \w     75.00 184.00   1.00    1.00    --   95.80  45.00-120.00  109
 20  \w     79.00 128.00   1.00    1.00    --   95.80 -82.00 120.00   49
 21  \w     65.00 153.00   1.00    1.00    --   95.80  77.00 150.00   88
 22  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -60.00   25
 23  \w      7.00  84.00   1.00    1.00    --   95.80 -61.00-120.00   77
 24  \w     88.00 118.00   1.00    1.00    --   95.80 -61.00-120.00   30
 25  \w     65.00  93.00   1.00    1.00    --   95.80  77.00 -30.00   28
 26  \w     63.00  89.00   1.00    1.00    --   95.80  82.00-150.00   26
 27  \w     65.00  92.00   1.00    1.00    --   95.80  77.00-120.00   27
 28  \w     65.00  90.00   1.00    1.00    --   95.80  77.00 -90.00   25
 29  \w     31.00 128.00   1.00    1.00    --   95.80 -82.00  30.00   97
 30  \w     68.00  94.00   1.00    1.00    --   95.80  77.00  60.00   26
 31  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 -60.00   26
 32  \w    115.00 179.00   1.00    1.00    --   95.80  75.00 140.12   64
 33  \w     32.00  68.00   1.00    1.00    --   95.80 -82.00 120.00   36
 34  \w     74.00 100.00   1.00    1.00    --   95.80  61.00 -30.00   26
 35  \w     76.00 111.00   1.00    1.00    --   95.80  45.00 150.00   35
 36  \w     64.00  89.00   1.00    1.00    --   95.80  82.00   0.00   25
 37  \w    118.00 179.00   1.00    1.00    --   95.80  61.00 -30.00   61
 38  \w     64.00  89.00   1.00    1.00    --   95.80  82.00 120.00   25
 39  \w     76.00 138.00   1.00    1.00    --   95.80  45.00  30.00   62
 40  \w     72.00  99.00   1.00    1.00    --   95.80  61.00 120.00   27
 41  \w    102.00 128.00   1.00    1.00    --   95.80  61.00 120.00   26
 42  \w     63.00  89.00   1.00    1.00    --   95.80  82.00 150.00   26
 43  \w     75.00 101.00   1.00    1.00    --   95.80  45.00-150.00   26
 44  \w    110.00 183.00   1.00    1.00    --   95.80  45.00-150.00   73
 45  \w     71.00 102.00   1.00    1.00    --   95.80  61.00 -60.00   31
 46  \w     73.00  98.00   1.00    1.00    --   95.80  61.00  60.00   25
 47  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  30.00   25
 48  \w     31.00  57.00   1.00    1.00    --   95.80 -82.00 -60.00   26
 49  \w     83.00 127.00   1.00    1.00    --   95.80 -82.00 -60.00   44
 50  \w     63.00  88.00   1.00    1.00    --   95.80  82.00 -30.00   25
 51  \w     65.00  90.00   1.00    1.00    --   95.80  77.00  90.00   25
 52  \w    149.00 174.00   1.00    1.00    --   95.80  77.00-180.00   25
 53  \w     75.00 121.00   1.00    1.00    --   95.80  45.00  60.00   46
 54  \w     63.00  88.00   1.00    1.00    --   95.80  82.00-180.00   25
 55  \w     65.00  91.00   1.00    1.00    --   95.80  77.00-180.00   26
 56  \w     78.00 177.00   1.00    1.00    --   95.80  45.00 -90.00   99
 57  \w     67.00  93.00   1.00    1.00    --   95.80  75.00 140.12   26
 58  \w     15.00 121.00   1.00    1.00    --   95.80 -82.00-120.00  106
 59  \w     68.00 172.00   1.00    1.00    --   95.80  68.00  67.17  104
 60  \w     68.00 173.00   1.00    1.00    --   95.80  68.00  90.96  105
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1438220000
_diffrn_orient_matrix_UB_12      0.0597425000
_diffrn_orient_matrix_UB_13      -0.0410725000
_diffrn_orient_matrix_UB_21      0.0794038000
_diffrn_orient_matrix_UB_22      -0.0260548000
_diffrn_orient_matrix_UB_23      -0.0766080000
_diffrn_orient_matrix_UB_31      -0.0675513000
_diffrn_orient_matrix_UB_32      -0.1576630000
_diffrn_orient_matrix_UB_33      -0.0028644000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0500
_diffrn_reflns_av_unetI/netI     0.0154
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            27293
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.015
_diffrn_reflns_theta_max         67.015
_diffrn_reflns_theta_min         4.991
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.605
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.32a (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.218
_exptl_crystal_description       block
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.095
_refine_diff_density_rms         0.022
_refine_ls_abs_structure_details
;
 Flack x determined using 1003 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(7)
_refine_ls_extinction_coef       0.0152(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2443
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0252
_refine_ls_R_factor_gt           0.0250
_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^)+(0.0295P)^2^+0.1841P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0625
_refine_ls_wR_factor_ref         0.0626
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                2421
_reflns_number_total             2443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc04996h2.cif
_cod_data_source_block           exp_1837
_cod_database_code               7129393
_shelx_shelxl_version_number     2016/6
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C9(H9A,H9B), C15(H15A,H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_shelx_res_checksum              77958
_shelx_hkl_checksum              77035
_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 3.476
_oxdiff_exptl_absorpt_empirical_full_min 0.568