Inherent directing group-enabled Co(III)-catalyzed C-H allylation/vinylation of isoquinolones.
Sachin, ?; Sharma, Tamanna; Chandra, Devesh; Sumit, ?; Sharma, Upendra; Chemical communications (Cambridge, England) 60 (2024) 5626–5629; doi:10.1039/d4cc01146e

data_7133019
_publ_section_title
;
 Inherent directing group-enabled Co(III)-catalyzed C-H
 allylation/vinylation of isoquinolones.
;
_journal_issue                   43
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5626
_journal_page_last               5629
_journal_paper_doi               10.1039/d4cc01146e
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C18 H14 Cl N O'
_chemical_formula_sum            'C18 H14 Cl N O'
_chemical_formula_weight         295.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-10-10
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2024-05-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.254(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8569(6)
_cell_length_b                   16.8285(13)
_cell_length_c                   11.2120(8)
_cell_measurement_reflns_used    1763
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.3850
_cell_measurement_theta_min      4.8610
_cell_volume                     1436.81(19)
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac5-024 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9974
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.983
_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   -101.00 -51.00   1.00    1.00    --  -24.78 -57.00-180.00   50
  2  \w    -63.00  42.00   1.00    1.00    --  -24.78  77.00  60.00  105
  3  \w    -15.00  37.00   1.00    1.00    --   24.78  77.00 150.00   52
  4  \w   -125.00 -48.00   1.00    1.50    --  -69.25 178.00-120.00   77
  5  \w    114.00 155.00   1.00    1.50    --   69.25 111.00-180.00   41
  6  \w    109.00 154.00   1.00    1.50    --   69.25 111.00 -30.00   45
  7  \w    106.00 153.00   1.00    1.50    --   69.25 111.00  60.00   47
  8  \w    -21.00 159.00   1.00    1.50    --   69.25  12.00 -60.00  180
  9  \w    122.00 165.00   1.00    2.44    --  113.72  43.00-180.00   43
 10  \w     83.00 118.00   1.00    2.44    --  113.72  43.00-180.00   35
 11  \w     26.00 158.00   1.00    2.44    --  113.72 -21.00 -30.00  132
 12  \w     25.00 106.00   1.00    2.44    --  113.72 -89.00-120.00   81
 13  \w     29.00 108.00   1.00    2.44    --  113.72-104.00  90.00   79
 14  \w     48.00 103.00   1.00    2.44    --  113.72-104.00-150.00   55
 15  \w     34.00 143.00   1.00    2.44    --  113.72 -65.00  60.00  109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1950274000
_diffrn_orient_matrix_UB_12      -0.0146465000
_diffrn_orient_matrix_UB_13      0.0629698000
_diffrn_orient_matrix_UB_21      -0.0396565000
_diffrn_orient_matrix_UB_22      0.0108804000
_diffrn_orient_matrix_UB_23      0.1269498000
_diffrn_orient_matrix_UB_31      -0.0364565000
_diffrn_orient_matrix_UB_32      -0.0896821000
_diffrn_orient_matrix_UB_33      0.0049254000
_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  0.0256
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4102
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.974
_diffrn_reflns_theta_min         4.844
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.323
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.416
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.635
_exptl_crystal_size_mid          0.387
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0009(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2554
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0614
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0908P)^2^+0.1112P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1395
_refine_ls_wR_factor_ref         0.1540
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2042
_reflns_number_total             2554
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc01146e2.cif
_cod_data_source_block           ussrnb1_134_1_rt_cu_auto
_cod_depositor_comments          'Adding full bibliography for 7133019.cif.'
_cod_database_code               7133019
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C72  H56  Cl4  N4  O4  '
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C17(H17), C11(H11), C5(H5), C13(H13), C1(H1), C12(H12), C4(H4),
 C3(H3), C2(H2)
2.c X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
;
_shelx_res_checksum              5899
_shelx_hkl_checksum              20212
_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 1.541
_oxdiff_exptl_absorpt_empirical_full_min 0.700