Copper-catalyzed N-arylation of Isatins Employing Aryl(TMP)iodonium Salts
Rakshit, Ankita J.; Saikia, Raktim Abha; Deka, Snata; Thakur, Ashim Jyoti; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D5OB01451D

data_7160908
_publ_section_title
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 Copper-catalyzed N-arylation of Isatins Employing Aryl(TMP)iodonium Salts
;
_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01451D
_journal_year                    2025
_chemical_formula_moiety         'C14 H8 Cl N O2'
_chemical_formula_sum            'C14 H8 Cl N O2'
_chemical_formula_weight         257.66
_chemical_name_systematic        1-(4-chlorophenyl)isatin
_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             2025-06-03
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-06-03 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   3.9146(19)
_cell_length_b                   13.289(7)
_cell_length_c                   21.939(11)
_cell_measurement_reflns_used    489
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      12.64
_cell_measurement_theta_min      3.07
_cell_volume                     1141.3(10)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.2063
_diffrn_reflns_av_unetI/netI     0.1942
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            16725
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.516
_diffrn_reflns_theta_min         1.792
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.325
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4360
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1213 before and 0.0853 after correction.
The Ratio of minimum to maximum transmission is 0.5847.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       needle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2892
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.931
_refine_ls_R_factor_all          0.2295
_refine_ls_R_factor_gt           0.0816
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1679
_refine_ls_wR_factor_ref         0.2374
_reflns_Friedel_coverage         0.663
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                1092
_reflns_number_total             2892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01451d3.cif
_cod_data_source_block           vd76_a
_cod_database_code               7160908
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C2-C1
 1.35 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C14(H14), C7(H7), C4(H4), C13(H13), C11(H11), C6(H6), C5(H5)
;
_shelx_res_checksum              50803
_olex2_submission_special_instructions 'No special instructions were received'