Harnessing sulfilimine as an oxidizing directing group in Cp*Co(iii)-catalyzed [4+2] annulation with alkynes and 1,3-diynes
Ghosh, Arijit; Pawar, Amit B.; Chemical Communications 61 (2025) 8240–8243; doi:10.1039/D5CC01230A

data_7134524
_publ_section_title
;
 Harnessing sulfilimine as an oxidizing directing group in
 Cp*Co(iii)-catalyzed [4+2] annulation with alkynes and 1,3-diynes
;
_journal_issue                   45
_journal_name_full               'Chemical Communications'
_journal_page_first              8240
_journal_page_last               8243
_journal_paper_doi               10.1039/D5CC01230A
_journal_volume                  61
_journal_year                    2025
_chemical_formula_moiety         'C31 H31 N O'
_chemical_formula_sum            'C31 H31 N O'
_chemical_formula_weight         433.57
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-08-29
_audit_creation_method
;
Olex2 1.5-ac5-024
(compiled 2022.04.12 svn.rca3783a0 for Rigaku Oxford Diffraction, GUI svn.r6498)
;
_audit_update_record
;
2025-02-21 deposited with the CCDC.	2025-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.422(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5297(4)
_cell_length_b                   13.4796(4)
_cell_length_c                   18.0553(5)
_cell_measurement_reflns_used    2439
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.8640
_cell_measurement_theta_min      4.1080
_cell_volume                     2560.41(14)
_computing_cell_refinement       'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_computing_data_collection
'CrysAlisPro system (CCD 43.101a (release 13-12-2023))'
_computing_data_reduction        'CrysAlisPro 1.171.43.101a (Rigaku OD, 2023)'
_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 0.989
_diffrn_measured_fraction_theta_max 0.979
_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     32.00  59.00   1.00    1.00    --  -24.78  37.00  90.00   27
  2  \w    -84.00  30.00   1.00    1.00    --  -24.78  37.00  90.00  114
  3  \w    -19.00  39.00   1.00    1.00    --   24.78  77.00-180.00   58
  4  \w   -111.00 -85.00   1.00    1.50    --  -69.25 -96.00-148.00   26
  5  \w   -158.00-132.00   1.00    1.50    --  -69.25 -96.00-148.00   26
  6  \w    108.00 152.00   1.00    1.50    --   69.25 111.00   0.00   44
  7  \w    106.00 151.00   1.00    1.50    --   69.25  77.00 -90.00   45
  8  \w    -12.00 131.00   1.00    1.50    --   69.25 -37.00 -60.00  143
  9  \w    106.00 148.00   1.00    1.50    --   69.25  77.00  30.00   42
 10  \w     19.00 107.00   1.00    1.50    --   69.25-111.00 150.00   88
 11  \w     33.00 178.00   1.00    2.99    --  113.72 -32.00 -30.00  145
 12  \w     27.00 166.00   1.00    2.99    --  113.72 -21.00 120.00  139
 13  \w     42.00 150.00   1.00    2.99    --  113.72 -54.00 150.00  108
 14  \w    119.00 149.00   1.00    2.99    --  113.72 104.00  90.00   30
 15  \w    104.00 139.00   1.00    2.99    --  113.72  77.00 150.00   35
 16  \w    125.00 168.00   1.00    2.99    --  113.72 138.00  30.00   43
 17  \w     27.00  95.00   1.00    2.99    --  113.72-104.00 -30.00   68
;
_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      0.1452634000
_diffrn_orient_matrix_UB_12      -0.0042509000
_diffrn_orient_matrix_UB_13      -0.0060031000
_diffrn_orient_matrix_UB_21      -0.0173611000
_diffrn_orient_matrix_UB_22      -0.0404456000
_diffrn_orient_matrix_UB_23      -0.0796100000
_diffrn_orient_matrix_UB_31      -0.0005774000
_diffrn_orient_matrix_UB_32      0.1068675000
_diffrn_orient_matrix_UB_33      -0.0304322000
_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  0.0309
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            7700
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.069
_diffrn_reflns_theta_min         4.094
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.43.101a (Rigaku Oxford Diffraction, 2023)
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    1.125
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.385
_exptl_crystal_size_mid          0.303
_exptl_crystal_size_min          0.179
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         4678
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0953
_refine_ls_R_factor_gt           0.0748
_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^)+(0.1506P)^2^+0.0327P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2116
_refine_ls_wR_factor_ref         0.2507
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3240
_reflns_number_total             4678
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01230a2.cif
_cod_data_source_block           ag_tbu_rt_cu_auto
_cod_depositor_comments
'Adding full bibliography for 7134523--7134524.cif.'
_cod_database_code               7134524
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'C31 H31 N1 O1 '
_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
2.a Aromatic/amide H refined with riding coordinates:
 C24(H24), C27(H27), C23(H23), C26(H26), C13(H13), C12(H12), C6(H6), C3(H3),
 C16(H16), C5(H5), C15(H15), C4(H4)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C21(H21A,H21B,H21C), C20(H20A,H20B,H20C), C29(H29A,H29B,
 H29C), C31(H31A,H31B,H31C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              64415
_shelx_hkl_checksum              85056
_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 1.852
_oxdiff_exptl_absorpt_empirical_full_min 0.739