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_1569454
_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         'C31 H24 N2 O2 S'
_chemical_formula_sum            'C31 H25 N2 O2 S'
_chemical_formula_weight         489.59
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2022-08-30
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-03-13 deposited with the CCDC.	2023-06-08 downloaded from the CCDC.
;
_cell_angle_alpha                98.03(2)
_cell_angle_beta                 92.58(2)
_cell_angle_gamma                90.20(2)
_cell_formula_units_Z            2
_cell_length_a                   8.348(5)
_cell_length_b                   9.154(5)
_cell_length_c                   16.683(9)
_cell_measurement_reflns_used    7524
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.40
_cell_measurement_theta_min      2.25
_cell_volume                     1261.0(12)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 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 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298.0
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0623
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39197
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.026
_diffrn_reflns_theta_min         2.787
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.160
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6291
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1264 before and 0.0645 after correction.
The Ratio of minimum to maximum transmission is 0.8437.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colour
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       cube
_exptl_crystal_F_000             514
_refine_diff_density_max         0.304
_refine_diff_density_min         -0.385
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 3137 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     653
_refine_ls_number_reflns         11140
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0613P)^2^+0.1229P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1304
_reflns_Friedel_coverage         0.913
_reflns_Friedel_fraction_full    0.935
_reflns_Friedel_fraction_max     0.790
_reflns_number_gt                8118
_reflns_number_total             11140
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc01787g2.cif
_cod_data_source_block           awjl_b
_cod_depositor_comments
'Adding full bibliography for 1569453--1569454.cif.'
_cod_original_cell_volume        1260.9(12)
_cod_database_code               1569454
_shelx_shelxl_version_number     2018/3
_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:
 C52(H52), C7(H7), C11(H11), C41(H41), C51(H51), C19(H19), C48(H48), C13(H13),
 C34(H34), C10(H10), C21(H21), C20(H20), C35(H35), C38(H38), C3(H3), C43(H43),
 C4(H4), C12(H12), C27(H27), C42(H42), C45(H45), C57(H57), C26(H26), C50(H50),
 C49(H49), C18(H18), C14(H14), C60(H60), C17(H17), C61(H61), C44(H44), C62(H62),
  C24(H24), C23(H23), C22(H22), C56(H56)
2.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C29(H29A,H29B,H29C), C32(H32A,H32B,H32C), C55(H55A,H55B,H55C)
;
_shelx_res_checksum              68369
_shelx_hkl_checksum              95173
_olex2_submission_special_instructions 'No special instructions were received'