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_7160910
_publ_section_title
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 Copper-catalyzed N-arylation of Isatins Employing Aryl(TMP)iodonium Salts
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_journal_name_full               'Organic &amp; Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01451D
_journal_year                    2025
_chemical_formula_moiety         'C14 H8 Br N O2'
_chemical_formula_sum            'C14 H8 Br N O2'
_chemical_formula_weight         302.12
_chemical_name_common            1-(4-bromophenyl)isatin
_chemical_name_systematic        1-(4-bromophenyl)indoline-2,3-dione
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-12
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-06-12 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                98.65(5)
_cell_angle_beta                 88.67(5)
_cell_angle_gamma                89.92(5)
_cell_formula_units_Z            8
_cell_length_a                   3.938(6)
_cell_length_b                   13.90(2)
_cell_length_c                   43.76(6)
_cell_measurement_reflns_used    11731
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.108
_cell_measurement_theta_min      1.413
_cell_volume                     2367(6)
_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  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.920
_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_unetI/netI     0.4577
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11731
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.108
_diffrn_reflns_theta_min         1.413
_exptl_absorpt_coefficient_mu    3.465
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.792
_refine_diff_density_min         -1.488
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         11731
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.842
_refine_ls_R_factor_all          0.2525
_refine_ls_R_factor_gt           0.0983
_refine_ls_shift/su_max          0.003
_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          0.2385
_refine_ls_wR_factor_ref         0.3318
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4339
_reflns_number_total             11731
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob01451d3.cif
_cod_data_source_block           ajt_164p_181124_0u
_cod_database_code               7160910
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
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1. Others
 Fixed Uiso: H5D(0.038) H5C(0.037) H7B(0.03) H14C(0.037) H7A(0.031) H7D(0.033)
 H7C(0.03) H12C(0.04) H6D(0.044) H10C(0.032) H6C(0.036) H5A(0.032) H13C(0.04)
 H14D(0.033) H11D(0.048) H5B(0.032) H14B(0.035) H6B(0.034) H10D(0.034)
 H11A(0.047) H11C(0.044) H13B(0.031) H12A(0.046) H14A(0.045) H12D(0.047)
 H13D(0.045) H10B(0.04) H11B(0.041) H10A(0.043) H12B(0.055) H6A(0.04)
 H13A(0.047)
 Fixed X: H5D(0.506281) H5C(-0.339443) H7B(0.190957) H14C(0.194892)
 H7A(1.133909) H7D(0.635978) H7C(-0.30094) H12C(-0.034338) H6D(0.431486) H10C(-
 0.219293) H6C(-0.479161) H5A(1.02275) H13C(0.185531) H14D(0.761837)
 H11D(1.09212) H5B(0.142452) H14B(0.696594) H6B(0.035751) H10D(1.120833)
 H11A(1.233131) H11C(-0.235488) H13B(0.680134) H12A(1.421565) H14A(1.624992)
 H12D(0.924158) H13D(0.738242) H10B(0.258093) H11B(0.267663) H10A(1.258982)
 H12B(0.466937) H6A(0.924944) H13A(1.597893)
 Fixed Y: H5D(0.312617) H5C(0.773928) H7B(0.592305) H14C(0.934671)
 H7A(1.117518) H7D(0.383599) H7C(0.905651) H12C(0.995173) H6D(0.41791)
 H10C(0.730327) H6C(0.903059) H5A(1.185678) H13C(1.04496) H14D(0.135183)
 H11D(0.458533) H5B(0.730362) H14B(0.567921) H6B(0.597229) H10D(0.386874)
 H11A(1.290821) H11C(0.841384) H13B(0.454169) H12A(1.131073) H14A(1.116601)
 H12D(0.369679) H13D(0.211814) H10B(0.768658) H11B(0.660809) H10A(1.365276)
 H12B(0.497593) H6A(1.082236) H13A(1.041599)
 Fixed Z: H5D(0.017983) H5C(0.041988) H7B(0.368969) H14C(0.164291)
 H7A(0.388475) H7D(0.11099) H7C(0.13122) H12C(0.256888) H6D(0.064259)
 H10C(0.211816) H6C(0.08023) H5A(0.482772) H13C(0.211577) H14D(0.170437)
 H11D(0.197205) H5B(0.457266) H14B(0.334373) H6B(0.421809) H10D(0.143734)
 H11A(0.278796) H11C(0.255751) H13B(0.29002) H12A(0.264678) H14A(0.354937)
 H12D(0.233994) H13D(0.222164) H10B(0.290799) H11B(0.242621) H10A(0.330917)
 H12B(0.244862) H6A(0.437179) H13A(0.304554)
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_shelx_res_checksum              88305
_olex2_submission_special_instructions 'No special instructions were received'