High-performance anionic stereogenic-at-cobalt(III) complex/halide salts/oxone catalytic system for enantioselective halocyclization of olefins.
Fang, Yi-Jun; Wu, Xiao-Bao; Wang, Qi-Ming; Xie, Zu-Kui; Yao, Chuan-Zhi; Jiang, Hua-Jie; Yu, Jie; Chemical communications (Cambridge, England) 61 (2025) 2814–2817; doi:10.1039/d4cc06610c

data_7134185
_publ_section_title
;
 High-performance anionic stereogenic-at-cobalt(III) complex/halide
 salts/oxone catalytic system for enantioselective halocyclization of
 olefins.
;
_journal_issue                   13
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2814
_journal_page_last               2817
_journal_paper_doi               10.1039/d4cc06610c
_journal_volume                  61
_journal_year                    2025
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C13 H17 Br N2 O4 S'
_chemical_formula_sum            'C13 H17 Br N2 O4 S'
_chemical_formula_weight         377.25
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2024-08-09
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-08-09 deposited with the CCDC.	2025-01-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.87(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.403(11)
_cell_length_b                   5.914(4)
_cell_length_c                   22.599(16)
_cell_measurement_reflns_used    744
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      19.085
_cell_measurement_theta_min      2.797
_cell_volume                     1602(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1062
_diffrn_reflns_av_unetI/netI     0.1727
_diffrn_reflns_Laue_measured_fraction_full 0.966
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            5439
_diffrn_reflns_point_group_measured_fraction_full 0.845
_diffrn_reflns_point_group_measured_fraction_max 0.846
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.675
_diffrn_reflns_theta_min         2.798
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.712
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1283 before and 0.0580 after correction.
The Ratio of minimum to maximum transmission is 0.5491.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_description       plate
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.907
_refine_diff_density_min         -0.407
_refine_diff_density_rms         0.101
_refine_ls_abs_structure_details
;
 Flack x determined using 289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2581
_refine_ls_number_restraints     19
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1754
_refine_ls_R_factor_gt           0.0782
_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^)+(0.0948P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1750
_refine_ls_wR_factor_ref         0.2212
_reflns_Friedel_coverage         0.584
_reflns_Friedel_fraction_full    0.696
_reflns_Friedel_fraction_max     0.696
_reflns_number_gt                1263
_reflns_number_total             2581
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc06610c2.cif
_cod_data_source_block           210713fyj
_cod_depositor_comments
'Adding full bibliography for 7134183--7134186.cif.'
_cod_database_code               7134185
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.687
_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. Uiso/Uaniso restraints and constraints
C2 \\sim C3 \\sim C4 \\sim C5: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
3.a Ternary CH refined with riding coordinates:
 C1(H1), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C10(H10), C12(H12), C13(H13)
3.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C)
;
_shelx_res_checksum              98375
_shelx_hkl_checksum              17207
_olex2_submission_special_instructions 'No special instructions were received'