Copper nanoparticle-catalyzed synthesis of N-arylated indoles, carbazoles, and N-alkylated indoles
Pandey, Ankit; Kaur, Bhupinder; Dwivedi, Khilesh C.; Balakrishna, Maravanji S.; New Journal of Chemistry 49 (2025) 17936–17950; doi:10.1039/D5NJ02820E

data_7064012
_publ_section_title
;
 Copper nanoparticle-catalyzed synthesis of N-arylated indoles,
 carbazoles, and N-alkylated indoles
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              17936
_journal_page_last               17950
_journal_paper_doi               10.1039/D5NJ02820E
_journal_volume                  49
_journal_year                    2025
_chemical_formula_moiety         '2(C28 H26 Cu I N O2 P)'
_chemical_formula_sum            'C56 H52 Cu2 I2 N2 O4 P2'
_chemical_formula_weight         1259.81
_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   mixed
_audit_creation_date             2025-01-06
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2025-02-17 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                82.501(2)
_cell_angle_beta                 77.156(2)
_cell_angle_gamma                76.439(2)
_cell_formula_units_Z            2
_cell_length_a                   12.3061(9)
_cell_length_b                   12.7758(8)
_cell_length_c                   17.5598(12)
_cell_measurement_reflns_used    5251
_cell_measurement_temperature    150.0
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.66
_cell_volume                     2607.7(3)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      150.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0751
_diffrn_reflns_av_unetI/netI     0.0369
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            123215
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.359
_diffrn_reflns_theta_min         1.902
_exptl_absorpt_coefficient_mu    2.108
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4826
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1438 before and 0.0867 after correction.
The Ratio of minimum to maximum transmission is 0.6421.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       block
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.67
_exptl_crystal_size_mid          0.057
_exptl_crystal_size_min          0.052
_refine_diff_density_max         1.691
_refine_diff_density_min         -1.349
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     625
_refine_ls_number_reflns         13021
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0324
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0349P)^2^+2.6486P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0768
_refine_ls_wR_factor_ref         0.0814
_reflns_Friedel_coverage         0.000
_reflns_number_gt                11042
_reflns_number_total             13021
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5nj02820e2.cif
_cod_data_source_block           Compound_9
_cod_depositor_comments
'Adding full bibliography for 7064007--7064013.cif.'
_cod_database_code               7064012
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.898
_shelx_estimated_absorpt_t_min   0.332
_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 Ternary CH refined with riding coordinates:
 C26'(H26'), C26(H26)
2.b Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C2(H2), C5'(H5'), C15'(H15'), C3(H3), C19'(H19'), C4'(H4'),
 C17'(H17'), C16'(H16'), C5(H5), C3'(H3'), C4(H4), C15(H15), C19(H19), C16(H16),
  C25'(H25'), C9'(H9'), C21'(H21'), C17(H17), C18'(H18'), C25(H25), C21(H21),
 C18(H18), C12'(H12'), C9(H9), C24(H24), C22'(H22'), C10'(H10'), C11'(H11'),
 C12(H12), C11(H11), C10(H10), C23'(H23'), C22(H22), C23(H23), C24'(H24')
2.c Idealised Me refined as rotating group:
 C28'(H28D,H28E,H28F), C27(H27A,H27B,H27C), C27'(H27D,H27E,H27F), C28(H28A,
 H28B,H28C)
;
_shelx_res_checksum              97112
_olex2_submission_special_instructions 'No special instructions were received'