Cobalt-catalyzed regioselective (4+2)-annulation of benzamides with allenyl carbinol acetates: access to 3-vinylisoquinolinones.
Kumar, Pravin; Dash, Om Prakash; Volla, Chandra M. R.; Chemical communications (Cambridge, England) 61 (2025) 16962–16965; doi:10.1039/d5cc04210k

data_7134995
_publ_section_title
;
 Cobalt-catalyzed regioselective (4+2)-annulation of benzamides with
 allenyl carbinol acetates: access to 3-vinylisoquinolinones.
;
_journal_issue                   87
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              16962
_journal_page_last               16965
_journal_paper_doi               10.1039/d5cc04210k
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C27 H20 N2 O, H2 O'
_chemical_formula_sum            'C27 H22 N2 O2'
_chemical_formula_weight         406.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'I -2ya'
_space_group_name_H-M_alt        'I 1 a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2025-07-22
_audit_creation_method
;
Olex2 1.5-ac6-016
(compiled 2024.01.13 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6897)
;
_audit_update_record
;
2025-07-23 deposited with the CCDC.	2025-09-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.124(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8439(2)
_cell_length_b                   38.1781(14)
_cell_length_c                   9.1909(5)
_cell_measurement_reflns_used    7199
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      27.3830
_cell_measurement_theta_min      2.1200
_cell_volume                     2045.26(15)
_computing_cell_refinement       'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_data_collection
'PROGRAM:BIS V6.2.16/2021-10-22 && APEX4 2021.4-0                                '
_computing_data_reduction        'CrysAlisPro 1.171.43.105a (Rigaku OD, 2024)'
_computing_molecular_graphics    'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-016 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \f    -62.01 170.99   1.00    4.00   9.42 -12.98 -31.50    --   233
  2  \w   -108.63  15.37   1.00    4.00    --  -12.98 -59.25  20.08  124
  3  \w   -108.63  15.37   1.00    4.00    --  -12.98 -59.25  71.08  124
  4  \w   -108.63  15.37   1.00    4.00    --  -12.98 -59.25 122.08  124
  5  \f    -24.02 159.98   1.00    4.00  16.12 -12.98 -59.25    --   184
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type
'Saxi-CrysAlisPro-abstract goniometer imported SAXI images'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0273891000
_diffrn_orient_matrix_UB_12      0.0136545000
_diffrn_orient_matrix_UB_13      -0.0481360000
_diffrn_orient_matrix_UB_21      0.0256560000
_diffrn_orient_matrix_UB_22      0.0112228000
_diffrn_orient_matrix_UB_23      0.0604778000
_diffrn_orient_matrix_UB_31      0.1157211000
_diffrn_orient_matrix_UB_32      -0.0057291000
_diffrn_orient_matrix_UB_33      0.0038351000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1006
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            20772
_diffrn_reflns_point_group_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         2.134
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.105a (Rigaku Oxford Diffraction, 2024)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_description       plate
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.076
_exptl_crystal_size_mid          0.054
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1324 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         3420
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0492
_refine_ls_R_factor_gt           0.0454
_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^)+(0.0802P)^2^+0.3916P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1273
_reflns_Friedel_coverage         0.894
_reflns_Friedel_fraction_full    0.902
_reflns_Friedel_fraction_max     0.902
_reflns_number_gt                3207
_reflns_number_total             3420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc04210k2.cif
_cod_data_source_block           cmrv_op_pk_58_autored
_cod_depositor_comments          'Adding full bibliography for 7134995.cif.'
_cod_database_code               7134995
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.998
_shelx_estimated_absorpt_t_min   0.994
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C005(H005), C009(H009), C00A(H00A), C00B(H00B), C00C(H00C), C00F(H00F),
 C00G(H00G), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00T(H00T), C00U(H00U)
2.c Idealised Me refined as rotating group:
 C00S(H00D,H00E,H00H)
;
_shelx_res_checksum              23660
_shelx_hkl_checksum              30024
_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 1.756
_oxdiff_exptl_absorpt_empirical_full_min 0.479