Metal-free site-selective functionalization with cyclic diaryl λ<sup>3</sup>-chloranes: suppression of benzyne formation for ligand-coupling reactions.
Patra, Koushik; Dey, Manas Pratim; Baidya, Mahiuddin; Chemical science 15 (2024) 16605–16611; doi:10.1039/d4sc04108a

data_1572592
_publ_section_title
;
 Metal-free site-selective functionalization with cyclic diaryl
 &#x3bb;<sup>3</sup>-chloranes: suppression of benzyne formation for
 ligand-coupling reactions.
;
_journal_issue                   40
_journal_name_full               'Chemical science'
_journal_page_first              16605
_journal_page_last               16611
_journal_paper_doi               10.1039/d4sc04108a
_journal_volume                  15
_journal_year                    2024
_chemical_formula_sum            'C20 H22 Cl N S2'
_chemical_formula_weight         375.95
_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   geom
_audit_block_doi                 10.5517/ccdc.csd.cc2jkvml
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2024-03-17 deposited with the CCDC.	2024-09-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
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_cell_angle_gamma                90
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_cell_length_c                   14.347(2)
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_cell_measurement_theta_min      2.77
_cell_volume                     1910.0(5)
_computing_cell_refinement       'APEX4/SAINT (Bruker, 2021)'
_computing_data_collection       'APEX4 (Bruker, 2021)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2021)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019), WinGX'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture Diffractometer'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            55860
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.344
_diffrn_reflns_theta_min         3.118
_diffrn_source                   'fine focus sealed tube'
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5420
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.307
_exptl_crystal_description       block
_exptl_crystal_F_000             792
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_exptl_crystal_size_mid          0.147
_exptl_crystal_size_min          0.092
_refine_diff_density_max         0.393
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_refine_ls_number_reflns         3879
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0620
_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^)+(0.0681P)^2^+1.8933P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1506
_refine_ls_wR_factor_ref         0.1619
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3071
_reflns_number_total             3879
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4sc04108a2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 1572592--1572593.cif.'
_cod_original_cell_volume        1909.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1572592
_shelx_shelxl_version_number     2019/3
_shelx_estimated_absorpt_t_min   0.906
_shelx_estimated_absorpt_t_max   0.962
_shelx_res_checksum              51810
_shelx_hkl_checksum              20860