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_7134523
_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         'C15 H19 N O'
_chemical_formula_sum            'C15 H19 N O'
_chemical_formula_weight         229.31
_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             2024-07-25
_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                 102.511(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7665(7)
_cell_length_b                   18.8687(13)
_cell_length_c                   8.1487(5)
_cell_measurement_reflns_used    1382
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      68.7640
_cell_measurement_theta_min      4.6920
_cell_volume                     1315.89(16)
_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 0.991
_diffrn_measured_fraction_theta_max 0.974
_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    -61.00  16.00   1.00    1.00    --  -24.78  57.00   0.00   77
  2  \w     21.00  52.00   1.00    1.00    --  -24.78  57.00   0.00   31
  3  \w     31.00  76.00   1.00    1.00    --   24.78  57.00  90.00   45
  4  \w     -7.00  26.00   1.00    1.00    --   24.78  57.00  90.00   33
  5  \w   -123.00 -48.00   1.00    2.00    --  -69.25 178.00  30.00   75
  6  \w   -157.00 -84.00   1.00    2.00    --  -69.25 -77.00-150.00   73
  7  \w   -116.00 -83.00   1.00    2.00    --  -69.25 -77.00 150.00   33
  8  \w     67.00 138.00   1.00    2.00    --   69.25 178.00-180.00   71
  9  \w    103.00 131.00   1.00    2.00    --   69.25  77.00-180.00   28
 10  \w     26.00 147.00   1.00    2.00    --   69.25  50.00-120.00  121
 11  \w    136.00 178.00   1.00    2.52    --  113.72  21.00  30.00   42
 12  \w     75.00 133.00   1.00    2.52    --  113.72  21.00  30.00   58
 13  \w     30.00  72.00   1.00    2.52    --  113.72  21.00  30.00   42
 14  \w     26.00 153.00   1.00    2.52    --  113.72 -77.00 -30.00  127
 15  \w     28.00 108.00   1.00    2.52    --  113.72-104.00 150.00   80
 16  \w     54.00 104.00   1.00    2.52    --  113.72-104.00  90.00   50
 17  \w     46.00 160.00   1.00    2.52    --  113.72 -43.00 -60.00  114
;
_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      -0.1783031000
_diffrn_orient_matrix_UB_12      -0.0065168000
_diffrn_orient_matrix_UB_13      -0.0206265000
_diffrn_orient_matrix_UB_21      0.0196366000
_diffrn_orient_matrix_UB_22      0.0018873000
_diffrn_orient_matrix_UB_23      0.1924454000
_diffrn_orient_matrix_UB_31      -0.0147560000
_diffrn_orient_matrix_UB_32      0.0813759000
_diffrn_orient_matrix_UB_33      -0.0061189000
_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  0.0205
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            3772
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.151
_diffrn_reflns_theta_min         4.687
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.559
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.655
_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    1.157
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       monoclinic
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.642
_exptl_crystal_size_mid          0.152
_exptl_crystal_size_min          0.144
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.987
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     160
_refine_ls_number_reflns         2393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0568
_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^)+(0.1150P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1546
_refine_ls_wR_factor_ref         0.1760
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1786
_reflns_number_total             2393
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5cc01230a2.cif
_cod_data_source_block           ag_rt_cu_auto
_cod_depositor_comments
'Adding full bibliography for 7134523--7134524.cif.'
_cod_database_code               7134523
_shelx_shelxl_version_number     2018/1
_chemical_oxdiff_formula         'c h n o'
_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 Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C10(H10A,H10B), C14(H14A,H14B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C1(H1A), C3(H3), C2(H2)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              51535
_shelx_hkl_checksum              30277
_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 1.454
_oxdiff_exptl_absorpt_empirical_full_min 0.786