Cobalt-catalyzed enantioselective C-H/N-H annulation of aryl sulfonamides with allenes or alkynes: facile access to C-N axially chiral sultams.
Si, Xiao-Ju; Zhao, Xiaofang; Wang, Jianli; Wang, Xinhai; Zhang, Yuanshuo; Yang, Dandan; Song, Mao-Ping; Niu, Jun-Long; Chemical science 14 (2023) 7291–7303; doi:10.1039/d3sc01787g

data_1569453
_publ_section_title
;
 Cobalt-catalyzed enantioselective C-H/N-H annulation of aryl sulfonamides
 with allenes or alkynes: facile access to C-N axially chiral sultams.
;
_journal_issue                   26
_journal_name_full               'Chemical science'
_journal_page_first              7291
_journal_page_last               7303
_journal_paper_doi               10.1039/d3sc01787g
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C28 H24 N2 O4 S'
_chemical_formula_sum            'C28 H24 N2 O4 S'
_chemical_formula_weight         484.55
_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             2022-08-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-02-14 deposited with the CCDC.	2023-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7020(3)
_cell_length_b                   10.7451(4)
_cell_length_c                   25.9020(9)
_cell_measurement_reflns_used    4827
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      73.0580
_cell_measurement_theta_min      3.4900
_cell_volume                     2421.94(15)
_computing_cell_refinement       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.27b (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.943
_diffrn_measured_fraction_theta_max 1.000
_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     -6.00  86.00   0.50    0.50    --    0.00  38.00  60.00  184
  2  \w     49.00  83.00   0.50    0.50    --    0.00  57.00 -60.00   68
  3  \w     10.00  62.00   0.50    0.50    --   98.80 -45.00 150.00  104
  4  \w     61.00  97.00   0.50    0.50    --   98.80  82.00-180.00   72
  5  \w      9.00  41.00   0.50    0.50    --   98.80 -61.00   0.00   64
  6  \w     55.00 122.00   0.50    0.50    --   98.80 -61.00   0.00  134
  7  \w     71.00 115.00   0.50    0.50    --   98.80 -45.00 150.00   88
  8  \w    107.00 176.00   0.50    0.50    --   98.80  82.00-180.00  138
  9  \w    136.00 182.00   0.50    0.50    --   98.80  61.00 120.00   92
 10  \w     73.00 119.00   0.50    0.50    --   98.80  61.00 120.00   92
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1234550000
_diffrn_orient_matrix_UB_12      -0.1018795000
_diffrn_orient_matrix_UB_13      0.0054482000
_diffrn_orient_matrix_UB_21      -0.0416042000
_diffrn_orient_matrix_UB_22      0.0153137000
_diffrn_orient_matrix_UB_23      -0.0574708000
_diffrn_orient_matrix_UB_31      0.1198652000
_diffrn_orient_matrix_UB_32      -0.0997479000
_diffrn_orient_matrix_UB_33      -0.0142764000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0895
_diffrn_reflns_av_unetI/netI     0.0984
_diffrn_reflns_Laue_measured_fraction_full 0.943
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            7568
_diffrn_reflns_point_group_measured_fraction_full 0.886
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         64.990
_diffrn_reflns_theta_min         3.413
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.497
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.27b (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       prism
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.469
_refine_diff_density_rms         0.094
_refine_ls_abs_structure_details
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.03(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.159
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3888
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.159
_refine_ls_R_factor_all          0.0840
_refine_ls_R_factor_gt           0.0589
_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^)+(0.1075P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1715
_refine_ls_wR_factor_ref         0.1748
_reflns_Friedel_coverage         0.638
_reflns_Friedel_fraction_full    0.809
_reflns_Friedel_fraction_max     0.865
_reflns_number_gt                3432
_reflns_number_total             3888
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01787g2.cif
_cod_data_source_block           hy
_cod_depositor_comments
'Adding full bibliography for 1569453--1569454.cif.'
_cod_database_code               1569453
_shelxl_version_number           2013-2
_chemical_oxdiff_usercomment     ' '
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.956
_reflns_odcompleteness_completeness 99.92
_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 Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C13(H13), C16(H16),
 C17(H17), C19(H19), C20(H20), C21(H21), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C28(H28A,H28B,H28C)
;
_shelx_res_checksum              5144
_shelx_hkl_checksum              61397
_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 3.569
_oxdiff_exptl_absorpt_empirical_full_min 0.407